Synthesis and crystal structures of halogenated oxa­thia­zolones and an unexpected pro­pan­amide

George, T.; McWilliams, S.W.; Masuda, J.D.; Schriver, M.J.

doi:10.1107/S2053229623002152

Synthesis and crystal structures of halogenated oxathiazolones and an unexpected propanamide

T. George, S. W. McWilliams, J. D. Masuda and M. J. Schriver

The known 1,3,4-oxathiazol-2-ones with crystal structures reported in the Cambridge Structural Database are limited (13 to date) and this article expands the library to 15. In addition, convenient starting materials for the future exploration of 1,3,4-oxathiazol-2-ones are detailed. An unexpected halogenated propanamide has also been identified as a by-product of one reaction, presumably reacting with HCl generated in situ. The space group of 5-[(E)-2-chloroethenyl]-1,3,4-oxathiazol-2-one, C₄H₂ClNO₂S, (1), is P2₁, with a high Z′ value of 6; the space group of rac-2,3-dibromo-3-chloropropanamide, C₃H₄Br₂ClNO, (2), is P2₁, with Z′ = 4; and the structure of rac-5-(1,2-dibromo-2-phenylethyl)-1,3,4-oxathiazol-2-one, C₁₀H₇Br₂NO₂S, (3), crystallizes in the space group Pca2₁, with Z′ = 1. Both of the structures of compounds 2 and 3 are modeled with two-component disorder and each molecular site hosts both of the enantiomers of the racemic pairs (S,S)/(R,R) and (R,S)/(S,R), respectively.

Keywords: oxathiazolone; intermolecular interaction; disorder; high Z′; propanamide; halogenation; heterocycle; antitubercular; crystal structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229623002152/dv3021sup1.cif Contains datablocks 1, 2, 3, global
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229623002152/dv30211sup2.hkl Contains datablock 1
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229623002152/dv30212sup3.hkl Contains datablock 2
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229623002152/dv30213sup4.hkl Contains datablock 3
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229623002152/dv30211sup5.cml Supplementary material
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229623002152/dv30212sup6.cml Supplementary material
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229623002152/dv30213sup7.cml Supplementary material

CCDC references: 2246703; 2246702; 2246701

Computing details top

For all structures, data collection: APEX4 (Bruker, 2021). Cell refinement: SAINT (Bruker, 2019) for (1); SAINT (Bruker, 2018) for (2), (3). Data reduction: SAINT (Bruker, 2019) for (1); SAINT (Bruker, 2018) for (2), (3). Program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a) for (1); SHELXT2018 (Sheldrick, 2015a) for (2), (3). For all structures, program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009), ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2020); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

5-[(E)-2-Chloroethenyl]-1,3,4-oxathiazol-2-one (1) top

Crystal data top

C₄H₂ClNO₂S	F(000) = 984
M_r = 163.58	D_x = 1.796 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 9.7839 (11) Å	Cell parameters from 5075 reflections
b = 10.2313 (11) Å	θ = 2.3–28.6°
c = 18.272 (2) Å	µ = 0.89 mm⁻¹
β = 97.125 (1)°	T = 125 K
V = 1814.9 (3) Å³	Block, colourless
Z = 12	0.11 × 0.09 × 0.09 mm

Data collection top

Bruker D8 Venture diffractometer	9072 independent reflections
Radiation source: microfocus sealed tube, Incoatec IµS 3.0	7423 reflections with I > 2σ(I)
Multilayer mirror monochromator	R_int = 0.032
Detector resolution: 7.3910 pixels mm^-1	θ_max = 29.2°, θ_min = 1.1°
φ and ω scans	h = −12→13
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −13→13
T_min = 0.703, T_max = 0.746	l = −24→24
23045 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.036	w = 1/[σ²(F_o²) + (0.0356P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.085	(Δ/σ)_max = 0.001
S = 1.05	Δρ_max = 0.36 e Å⁻³
9072 reflections	Δρ_min = −0.41 e Å⁻³
488 parameters	Absolute structure: Refined as an inversion twin.
1 restraint	Absolute structure parameter: 0.44 (8)
Primary atom site location: dual

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component inversion twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.21183 (12)	0.71322 (13)	−0.50527 (6)	0.0272 (3)
S1	0.13355 (12)	0.80145 (12)	−0.16277 (7)	0.0199 (3)
O1	0.1665 (3)	0.6455 (3)	−0.26784 (16)	0.0185 (7)
O2	0.1639 (3)	0.5395 (4)	−0.15982 (16)	0.0260 (7)
N1	0.1388 (4)	0.8640 (4)	−0.2479 (2)	0.0207 (9)
C1	0.1567 (4)	0.6404 (5)	−0.1922 (2)	0.0194 (9)
C2	0.1565 (5)	0.7725 (5)	−0.2932 (3)	0.0201 (11)
C3	0.1679 (4)	0.7917 (5)	−0.3706 (2)	0.0210 (10)
H3	0.155002	0.876711	−0.391116	0.025*
C4	0.1961 (4)	0.6932 (5)	−0.4136 (2)	0.0214 (10)
H4	0.208059	0.608274	−0.392693	0.026*
Cl6	0.82218 (12)	0.53332 (12)	1.00683 (6)	0.0260 (3)
S6	0.86351 (11)	0.43606 (11)	0.66067 (6)	0.0199 (3)
O11	0.8409 (3)	0.5930 (3)	0.76582 (16)	0.0187 (7)
O12	0.8424 (3)	0.6988 (3)	0.65762 (15)	0.0269 (8)
N6	0.8600 (4)	0.3741 (4)	0.7462 (2)	0.0199 (9)
C21	0.8465 (4)	0.5978 (5)	0.6899 (2)	0.0174 (9)
C22	0.8491 (4)	0.4672 (5)	0.7917 (3)	0.0157 (10)
C23	0.8442 (4)	0.4512 (5)	0.8703 (2)	0.0183 (10)
H23	0.851058	0.365881	0.890943	0.022*
C24	0.8303 (4)	0.5529 (5)	0.9140 (2)	0.0202 (10)
H24	0.824801	0.638357	0.893524	0.024*
Cl5	0.50105 (12)	0.46063 (14)	0.67119 (6)	0.0272 (3)
S5	0.54187 (11)	0.55865 (12)	0.32488 (6)	0.0212 (3)
O9	0.4957 (3)	0.4039 (3)	0.42791 (18)	0.0198 (8)
O10	0.4708 (3)	0.3044 (3)	0.31701 (16)	0.0271 (8)
N5	0.5544 (4)	0.6172 (4)	0.41198 (19)	0.0216 (8)
C17	0.4969 (4)	0.4021 (5)	0.3515 (2)	0.0205 (10)
C18	0.5278 (4)	0.5271 (5)	0.4562 (3)	0.0197 (11)
C19	0.5296 (4)	0.5427 (5)	0.5348 (2)	0.0209 (10)
H19	0.550834	0.625887	0.556338	0.025*
C20	0.5023 (4)	0.4440 (5)	0.5780 (2)	0.0194 (10)
H20	0.482760	0.360684	0.556280	0.023*
Cl2	0.52737 (13)	0.29244 (13)	−0.17200 (6)	0.0306 (3)
S2	0.49491 (12)	0.19247 (11)	0.17457 (6)	0.0201 (3)
O3	0.5245 (3)	0.3491 (3)	0.06980 (16)	0.0187 (7)
O4	0.5267 (3)	0.4556 (4)	0.17784 (16)	0.0270 (7)
N2	0.4953 (4)	0.1310 (4)	0.08869 (19)	0.0215 (9)
C5	0.5175 (4)	0.3543 (4)	0.1450 (2)	0.0179 (9)
C6	0.5093 (4)	0.2239 (5)	0.0430 (2)	0.0169 (10)
C7	0.5103 (4)	0.2087 (5)	−0.0351 (2)	0.0177 (10)
H7	0.498981	0.123787	−0.056097	0.021*
C8	0.5265 (4)	0.3089 (6)	−0.0786 (2)	0.0215 (10)
H8	0.538220	0.393562	−0.057378	0.026*
Cl3	0.17278 (12)	0.54355 (13)	0.33616 (6)	0.0258 (3)
S3	0.19237 (12)	0.43315 (11)	−0.01105 (6)	0.0218 (3)
O5	0.1630 (3)	0.5920 (3)	0.09259 (17)	0.0198 (8)
O6	0.1356 (3)	0.6912 (3)	−0.01818 (16)	0.0283 (8)
N3	0.2080 (4)	0.3759 (4)	0.0764 (2)	0.0209 (9)
C9	0.1587 (4)	0.5936 (5)	0.0160 (2)	0.0192 (10)
C10	0.1901 (4)	0.4699 (5)	0.1213 (3)	0.0162 (10)
C11	0.1931 (4)	0.4558 (5)	0.2000 (2)	0.0182 (9)
H11	0.210038	0.372181	0.221905	0.022*
C12	0.1727 (4)	0.5577 (5)	0.2425 (2)	0.0202 (10)
H12	0.157529	0.641210	0.220259	0.024*
Cl4	0.83476 (13)	0.69470 (13)	0.16361 (6)	0.0269 (3)
S4	0.83374 (12)	0.80884 (11)	0.51123 (7)	0.0194 (3)
O7	0.8651 (3)	0.6503 (3)	0.40772 (15)	0.0172 (7)
O8	0.8897 (3)	0.5508 (3)	0.51863 (15)	0.0268 (7)
N4	0.8157 (4)	0.8656 (4)	0.4242 (2)	0.0199 (9)
C13	0.8679 (4)	0.6491 (5)	0.4844 (2)	0.0187 (9)
C14	0.8332 (4)	0.7732 (5)	0.3796 (3)	0.0170 (11)
C15	0.8237 (4)	0.7865 (5)	0.3002 (2)	0.0195 (10)
H15	0.803148	0.869426	0.278237	0.023*
C16	0.8433 (4)	0.6845 (5)	0.2576 (2)	0.0199 (10)
H16	0.862883	0.601981	0.280348	0.024*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0328 (6)	0.0339 (7)	0.0153 (6)	0.0039 (6)	0.0041 (4)	0.0000 (5)
S1	0.0261 (6)	0.0177 (6)	0.0161 (6)	0.0009 (5)	0.0040 (4)	−0.0020 (5)
O1	0.0234 (15)	0.0150 (17)	0.0170 (17)	−0.0005 (13)	0.0021 (12)	0.0011 (14)
O2	0.0349 (18)	0.0196 (18)	0.0236 (18)	0.0008 (15)	0.0045 (13)	0.0052 (16)
N1	0.0262 (19)	0.018 (2)	0.018 (2)	−0.0004 (16)	0.0039 (15)	0.0008 (18)
C1	0.016 (2)	0.023 (2)	0.019 (2)	−0.0022 (17)	0.0011 (16)	−0.0016 (19)
C2	0.020 (2)	0.020 (3)	0.021 (3)	−0.0021 (19)	0.0028 (17)	0.000 (2)
C3	0.026 (2)	0.020 (3)	0.017 (2)	0.000 (2)	0.0017 (17)	0.002 (2)
C4	0.028 (2)	0.023 (3)	0.013 (2)	−0.001 (2)	−0.0015 (17)	0.003 (2)
Cl6	0.0332 (6)	0.0313 (7)	0.0137 (5)	0.0023 (6)	0.0034 (4)	−0.0017 (5)
S6	0.0257 (6)	0.0192 (6)	0.0154 (6)	0.0026 (5)	0.0048 (4)	−0.0006 (5)
O11	0.0236 (16)	0.0153 (18)	0.0174 (18)	0.0018 (13)	0.0036 (13)	−0.0004 (14)
O12	0.0410 (19)	0.0223 (19)	0.0176 (16)	0.0039 (14)	0.0039 (13)	0.0054 (14)
N6	0.0266 (19)	0.018 (2)	0.015 (2)	0.0010 (16)	0.0021 (14)	−0.0011 (17)
C21	0.0171 (19)	0.021 (2)	0.014 (2)	0.0016 (17)	0.0010 (16)	0.0003 (19)
C22	0.017 (2)	0.010 (3)	0.019 (2)	0.0020 (17)	0.0007 (16)	0.001 (2)
C23	0.020 (2)	0.017 (2)	0.017 (2)	−0.0007 (18)	−0.0002 (16)	0.001 (2)
C24	0.024 (2)	0.024 (3)	0.012 (2)	−0.002 (2)	0.0014 (16)	0.001 (2)
Cl5	0.0298 (6)	0.0383 (8)	0.0137 (5)	−0.0049 (6)	0.0039 (4)	0.0012 (5)
S5	0.0266 (5)	0.0219 (6)	0.0151 (5)	−0.0061 (5)	0.0023 (4)	0.0012 (5)
O9	0.0262 (17)	0.0176 (18)	0.0158 (18)	−0.0032 (14)	0.0030 (13)	−0.0001 (15)
O10	0.0400 (18)	0.0217 (18)	0.0199 (16)	−0.0055 (15)	0.0056 (13)	−0.0042 (14)
N5	0.0260 (19)	0.021 (2)	0.0175 (19)	−0.0039 (16)	0.0038 (15)	0.0003 (16)
C17	0.023 (2)	0.020 (2)	0.019 (2)	0.0024 (19)	0.0041 (18)	0.000 (2)
C18	0.016 (2)	0.022 (3)	0.021 (3)	0.000 (2)	0.0029 (18)	−0.001 (2)
C19	0.021 (2)	0.022 (3)	0.020 (2)	−0.001 (2)	0.0031 (17)	−0.005 (2)
C20	0.019 (2)	0.022 (3)	0.017 (2)	−0.0010 (19)	0.0012 (17)	−0.001 (2)
Cl2	0.0430 (7)	0.0353 (8)	0.0140 (5)	−0.0111 (6)	0.0053 (5)	−0.0005 (5)
S2	0.0252 (6)	0.0199 (7)	0.0155 (6)	−0.0005 (5)	0.0033 (4)	0.0014 (5)
O3	0.0251 (15)	0.0169 (17)	0.0138 (16)	−0.0004 (13)	0.0017 (12)	−0.0005 (13)
O4	0.0405 (19)	0.0238 (18)	0.0173 (16)	−0.0007 (15)	0.0064 (13)	−0.0021 (15)
N2	0.030 (2)	0.018 (2)	0.016 (2)	0.0010 (16)	0.0034 (15)	0.0000 (17)
C5	0.0180 (19)	0.018 (2)	0.017 (2)	0.0007 (16)	0.0008 (16)	0.0026 (18)
C6	0.018 (2)	0.017 (3)	0.016 (2)	0.0017 (19)	−0.0004 (16)	−0.001 (2)
C7	0.024 (2)	0.013 (2)	0.016 (2)	−0.0009 (19)	0.0040 (17)	−0.002 (2)
C8	0.025 (2)	0.025 (3)	0.014 (2)	−0.004 (2)	−0.0005 (17)	−0.002 (2)
Cl3	0.0318 (6)	0.0314 (7)	0.0145 (5)	0.0046 (5)	0.0042 (4)	−0.0009 (5)
S3	0.0307 (6)	0.0199 (7)	0.0147 (6)	0.0053 (5)	0.0023 (4)	−0.0002 (5)
O5	0.0282 (16)	0.0148 (18)	0.0162 (18)	0.0016 (13)	0.0024 (13)	−0.0012 (14)
O6	0.0434 (19)	0.0215 (19)	0.0202 (17)	0.0031 (15)	0.0042 (13)	0.0020 (15)
N3	0.030 (2)	0.018 (2)	0.014 (2)	0.0056 (16)	−0.0001 (15)	0.0005 (17)
C9	0.021 (2)	0.021 (2)	0.015 (2)	0.0009 (18)	−0.0015 (16)	−0.0009 (19)
C10	0.018 (2)	0.012 (3)	0.018 (2)	0.0022 (19)	−0.0012 (16)	0.001 (2)
C11	0.022 (2)	0.015 (2)	0.018 (2)	0.0011 (18)	0.0052 (16)	0.0007 (19)
C12	0.025 (2)	0.022 (3)	0.014 (2)	0.000 (2)	0.0019 (17)	0.001 (2)
Cl4	0.0366 (6)	0.0308 (7)	0.0134 (5)	0.0025 (5)	0.0040 (4)	−0.0002 (5)
S4	0.0260 (6)	0.0183 (6)	0.0138 (6)	0.0022 (5)	0.0018 (4)	−0.0021 (5)
O7	0.0231 (15)	0.0144 (16)	0.0145 (16)	0.0017 (12)	0.0043 (11)	0.0009 (13)
O8	0.0421 (18)	0.0205 (18)	0.0178 (15)	0.0054 (15)	0.0045 (13)	0.0042 (15)
N4	0.0225 (18)	0.021 (2)	0.016 (2)	−0.0011 (16)	0.0028 (14)	0.0005 (17)
C13	0.017 (2)	0.024 (2)	0.015 (2)	−0.0005 (17)	0.0036 (16)	−0.0024 (18)
C14	0.014 (2)	0.019 (3)	0.019 (3)	0.0009 (18)	0.0037 (16)	0.003 (2)
C15	0.023 (2)	0.020 (3)	0.016 (2)	0.0005 (19)	0.0042 (17)	0.006 (2)
C16	0.021 (2)	0.026 (3)	0.013 (2)	−0.001 (2)	0.0028 (16)	0.000 (2)

Geometric parameters (Å, º) top

Cl1—C4	1.714 (5)	Cl2—C8	1.716 (5)
S1—N1	1.688 (4)	S2—N2	1.691 (4)
S1—C1	1.757 (5)	S2—C5	1.764 (5)
O1—C1	1.398 (5)	O3—C5	1.385 (5)
O1—C2	1.379 (6)	O3—C6	1.372 (6)
O2—C1	1.187 (5)	O4—C5	1.195 (5)
N1—C2	1.276 (6)	N2—C6	1.284 (6)
C2—C3	1.445 (6)	C6—C7	1.438 (5)
C3—H3	0.9500	C7—H7	0.9500
C3—C4	1.328 (6)	C7—C8	1.319 (7)
C4—H4	0.9500	C8—H8	0.9500
Cl6—C24	1.719 (4)	Cl3—C12	1.717 (4)
S6—N6	1.692 (4)	S3—N3	1.691 (4)
S6—C21	1.753 (5)	S3—C9	1.757 (5)
O11—C21	1.396 (5)	O5—C9	1.395 (5)
O11—C22	1.371 (5)	O5—C10	1.368 (5)
O12—C21	1.188 (5)	O6—C9	1.185 (6)
N6—C22	1.277 (6)	N3—C10	1.291 (6)
C22—C23	1.451 (6)	C10—C11	1.443 (6)
C23—H23	0.9500	C11—H11	0.9500
C23—C24	1.329 (6)	C11—C12	1.330 (6)
C24—H24	0.9500	C12—H12	0.9500
Cl5—C20	1.713 (4)	Cl4—C16	1.712 (5)
S5—N5	1.691 (4)	S4—N4	1.681 (4)
S5—C17	1.746 (5)	S4—C13	1.750 (5)
O9—C17	1.398 (5)	O7—C13	1.399 (5)
O9—C18	1.383 (6)	O7—C14	1.380 (5)
O10—C17	1.192 (6)	O8—C13	1.189 (5)
N5—C18	1.274 (6)	N4—C14	1.274 (6)
C18—C19	1.443 (6)	C14—C15	1.448 (5)
C19—H19	0.9500	C15—H15	0.9500
C19—C20	1.328 (6)	C15—C16	1.331 (6)
C20—H20	0.9500	C16—H16	0.9500

N1—S1—C1	93.1 (2)	N2—S2—C5	92.9 (2)
C2—O1—C1	110.9 (4)	C6—O3—C5	111.9 (3)
C2—N1—S1	110.0 (4)	C6—N2—S2	109.9 (3)
O1—C1—S1	107.2 (3)	O3—C5—S2	106.9 (3)
O2—C1—S1	131.6 (4)	O4—C5—S2	131.6 (4)
O2—C1—O1	121.2 (4)	O4—C5—O3	121.5 (4)
O1—C2—C3	116.4 (5)	O3—C6—C7	116.2 (4)
N1—C2—O1	118.9 (4)	N2—C6—O3	118.4 (4)
N1—C2—C3	124.7 (5)	N2—C6—C7	125.4 (5)
C2—C3—H3	119.2	C6—C7—H7	119.0
C4—C3—C2	121.5 (5)	C8—C7—C6	122.0 (5)
C4—C3—H3	119.2	C8—C7—H7	119.0
Cl1—C4—H4	118.7	Cl2—C8—H8	118.7
C3—C4—Cl1	122.6 (4)	C7—C8—Cl2	122.6 (4)
C3—C4—H4	118.7	C7—C8—H8	118.7
N6—S6—C21	93.3 (2)	N3—S3—C9	93.2 (2)
C22—O11—C21	111.6 (4)	C10—O5—C9	112.0 (4)
C22—N6—S6	109.6 (3)	C10—N3—S3	109.8 (3)
O11—C21—S6	106.7 (3)	O5—C9—S3	106.7 (3)
O12—C21—S6	131.9 (4)	O6—C9—S3	132.1 (4)
O12—C21—O11	121.4 (4)	O6—C9—O5	121.2 (4)
O11—C22—C23	116.1 (4)	O5—C10—C11	116.9 (4)
N6—C22—O11	118.8 (4)	N3—C10—O5	118.2 (4)
N6—C22—C23	125.1 (4)	N3—C10—C11	124.8 (4)
C22—C23—H23	119.2	C10—C11—H11	119.4
C24—C23—C22	121.7 (5)	C12—C11—C10	121.2 (5)
C24—C23—H23	119.2	C12—C11—H11	119.4
Cl6—C24—H24	119.2	Cl3—C12—H12	118.9
C23—C24—Cl6	121.5 (4)	C11—C12—Cl3	122.3 (4)
C23—C24—H24	119.2	C11—C12—H12	118.9
N5—S5—C17	93.1 (2)	N4—S4—C13	93.4 (2)
C18—O9—C17	110.9 (4)	C14—O7—C13	110.9 (4)
C18—N5—S5	110.1 (3)	C14—N4—S4	110.0 (3)
O9—C17—S5	107.4 (3)	O7—C13—S4	106.9 (3)
O10—C17—S5	131.9 (4)	O8—C13—S4	132.1 (3)
O10—C17—O9	120.7 (4)	O8—C13—O7	120.9 (4)
O9—C18—C19	116.6 (5)	O7—C14—C15	116.2 (5)
N5—C18—O9	118.5 (4)	N4—C14—O7	118.7 (4)
N5—C18—C19	125.0 (5)	N4—C14—C15	125.1 (5)
C18—C19—H19	119.0	C14—C15—H15	119.4
C20—C19—C18	121.9 (5)	C16—C15—C14	121.2 (5)
C20—C19—H19	119.0	C16—C15—H15	119.4
Cl5—C20—H20	118.6	Cl4—C16—H16	118.4
C19—C20—Cl5	122.8 (4)	C15—C16—Cl4	123.2 (4)
C19—C20—H20	118.6	C15—C16—H16	118.4

S1—N1—C2—O1	0.6 (5)	S2—N2—C6—O3	1.6 (5)
S1—N1—C2—C3	−179.0 (3)	S2—N2—C6—C7	−178.2 (3)
O1—C2—C3—C4	−4.5 (6)	O3—C6—C7—C8	0.8 (6)
N1—S1—C1—O1	−0.3 (3)	N2—S2—C5—O3	−0.3 (3)
N1—S1—C1—O2	179.9 (4)	N2—S2—C5—O4	179.9 (4)
N1—C2—C3—C4	175.1 (5)	N2—C6—C7—C8	−179.4 (5)
C1—S1—N1—C2	−0.1 (3)	C5—S2—N2—C6	−0.7 (3)
C1—O1—C2—N1	−0.9 (6)	C5—O3—C6—N2	−1.9 (5)
C1—O1—C2—C3	178.8 (3)	C5—O3—C6—C7	177.9 (3)
C2—O1—C1—S1	0.7 (4)	C6—O3—C5—S2	1.2 (4)
C2—O1—C1—O2	−179.5 (4)	C6—O3—C5—O4	−179.0 (4)
C2—C3—C4—Cl1	−179.4 (3)	C6—C7—C8—Cl2	−179.8 (3)
S6—N6—C22—O11	0.7 (5)	S3—N3—C10—O5	0.1 (5)
S6—N6—C22—C23	−179.4 (3)	S3—N3—C10—C11	178.5 (3)
O11—C22—C23—C24	1.0 (6)	O5—C10—C11—C12	−1.1 (6)
N6—S6—C21—O11	0.7 (3)	N3—S3—C9—O5	0.5 (3)
N6—S6—C21—O12	179.3 (4)	N3—S3—C9—O6	−179.5 (5)
N6—C22—C23—C24	−178.8 (4)	N3—C10—C11—C12	−179.5 (4)
C21—S6—N6—C22	−0.8 (3)	C9—S3—N3—C10	−0.3 (3)
C21—O11—C22—N6	−0.2 (5)	C9—O5—C10—N3	0.3 (5)
C21—O11—C22—C23	180.0 (3)	C9—O5—C10—C11	−178.3 (3)
C22—O11—C21—S6	−0.5 (4)	C10—O5—C9—S3	−0.5 (4)
C22—O11—C21—O12	−179.2 (4)	C10—O5—C9—O6	179.5 (4)
C22—C23—C24—Cl6	179.1 (3)	C10—C11—C12—Cl3	178.9 (3)
S5—N5—C18—O9	0.3 (5)	S4—N4—C14—O7	−1.3 (5)
S5—N5—C18—C19	179.7 (3)	S4—N4—C14—C15	179.3 (3)
O9—C18—C19—C20	0.2 (6)	O7—C14—C15—C16	0.8 (6)
N5—S5—C17—O9	−0.7 (3)	N4—S4—C13—O7	0.9 (3)
N5—S5—C17—O10	179.8 (5)	N4—S4—C13—O8	−178.6 (4)
N5—C18—C19—C20	−179.2 (4)	N4—C14—C15—C16	−179.8 (5)
C17—S5—N5—C18	0.2 (4)	C13—S4—N4—C14	0.2 (3)
C17—O9—C18—N5	−0.9 (5)	C13—O7—C14—N4	2.1 (5)
C17—O9—C18—C19	179.7 (4)	C13—O7—C14—C15	−178.5 (3)
C18—O9—C17—S5	0.9 (4)	C14—O7—C13—S4	−1.7 (4)
C18—O9—C17—O10	−179.5 (4)	C14—O7—C13—O8	177.9 (4)
C18—C19—C20—Cl5	−178.9 (3)	C14—C15—C16—Cl4	−179.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O7ⁱ	0.95	2.82	3.738 (6)	163
C4—H4···N4ⁱⁱ	0.95	2.55	3.358 (7)	143
C23—H23···O5ⁱⁱⁱ	0.95	2.82	3.739 (6)	162
C24—H24···N3^iv	0.95	2.52	3.332 (7)	144
C19—H19···O9^iv	0.95	2.90	3.772 (6)	153
C20—H20···N5ⁱⁱⁱ	0.95	2.59	3.398 (7)	143
C7—H7···O3ⁱⁱ	0.95	2.83	3.742 (6)	162
C8—H8···N2ⁱ	0.95	2.51	3.306 (7)	142
C11—H11···O11ⁱⁱⁱ	0.95	2.91	3.785 (6)	153
C12—H12···N6^iv	0.95	2.47	3.262 (7)	141
C15—H15···O1ⁱ	0.95	2.85	3.724 (6)	154
C16—H16···N1ⁱⁱ	0.95	2.51	3.289 (7)	140

Symmetry codes: (i) −x+1, y+1/2, −z; (ii) −x+1, y−1/2, −z; (iii) −x+1, y−1/2, −z+1; (iv) −x+1, y+1/2, −z+1.

rac-2,3-Dibromo-3-chloropropanamide (2) top

Crystal data top

C₃H₄Br₂ClNO	F(000) = 992
M_r = 265.34	D_x = 2.409 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 6.5967 (2) Å	Cell parameters from 9991 reflections
b = 24.1942 (9) Å	θ = 3.2–29.2°
c = 9.1724 (3) Å	µ = 11.36 mm⁻¹
β = 91.904 (1)°	T = 100 K
V = 1463.12 (8) Å³	Plate, colourless
Z = 8	0.28 × 0.16 × 0.09 mm

Data collection top

Bruker D8 Venture diffractometer	6456 independent reflections
Radiation source: microfocus sealed tube, Incoatec IµS 3.0	5710 reflections with I > 2σ(I)
Multilayer mirror monochromator	R_int = 0.055
Detector resolution: 7.3910 pixels mm^-1	θ_max = 27.1°, θ_min = 2.2°
φ and ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −31→31
T_min = 0.003, T_max = 0.020	l = −11→11
55465 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.048	w = 1/[σ²(F_o²) + (0.0815P)² + 6.1207P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.139	(Δ/σ)_max < 0.001
S = 1.08	Δρ_max = 2.15 e Å⁻³
6456 reflections	Δρ_min = −1.09 e Å⁻³
330 parameters	Absolute structure: Refined as an inversion twin.
20 restraints	Absolute structure parameter: 0.36 (3)
Primary atom site location: dual

Special details top

Refinement. Refined as a 2-component inversion twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Br1	−0.50262 (18)	0.42390 (6)	0.39370 (15)	0.0336 (3)
Br2	0.0647 (2)	0.31951 (6)	0.50278 (17)	0.0367 (3)
O1	−0.0263 (13)	0.4412 (4)	0.3090 (8)	0.0248 (18)
N1	−0.0006 (16)	0.4709 (4)	0.5436 (10)	0.023 (2)
H1A	0.088735	0.496350	0.521778	0.027*
H1B	−0.039423	0.467379	0.633989	0.027*
C1	−0.0775 (18)	0.4376 (5)	0.4393 (13)	0.023 (2)
Cl1	−0.3898 (11)	0.2953 (3)	0.5101 (10)	0.0318 (14)	0.790 (19)
C2	−0.241 (2)	0.3975 (6)	0.4850 (15)	0.022 (3)	0.790 (19)
H2	−0.249977	0.397658	0.593604	0.027*	0.790 (19)
C3	−0.206 (2)	0.3400 (6)	0.4326 (15)	0.021 (3)	0.790 (19)
H3	−0.216375	0.338475	0.323696	0.025*	0.790 (19)
Br3	1.24147 (18)	0.42218 (6)	0.90633 (16)	0.0340 (3)
Br4	0.6737 (2)	0.31877 (7)	0.99094 (17)	0.0401 (3)
O2	0.7698 (13)	0.4431 (4)	0.8074 (9)	0.0241 (18)
N2	0.7492 (15)	0.4690 (4)	1.0423 (10)	0.022 (2)
H2B	0.660004	0.494956	1.020352	0.026*
H2C	0.789973	0.463832	1.133667	0.026*
C4	0.8221 (18)	0.4376 (5)	0.9381 (13)	0.023 (2)
Cl2	1.1256 (10)	0.2896 (3)	0.9763 (8)	0.0261 (12)	0.86 (2)
C5	0.985 (2)	0.3953 (6)	0.9835 (15)	0.024 (3)	0.86 (2)
H5	0.996687	0.392648	1.092269	0.028*	0.86 (2)
C6	0.938 (2)	0.3392 (6)	0.9189 (16)	0.024 (3)	0.86 (2)
H6	0.930485	0.341673	0.810009	0.029*	0.86 (2)
Br5	0.74005 (19)	0.57855 (6)	0.35901 (17)	0.0361 (3)
Br6	0.1720 (2)	0.68113 (7)	0.24460 (18)	0.0405 (4)
O3	0.2669 (13)	0.5582 (4)	0.4397 (9)	0.0232 (17)
N3	0.2421 (16)	0.5301 (5)	0.2051 (11)	0.026 (2)
H3B	0.157989	0.503158	0.225801	0.032*
H3C	0.278863	0.535009	0.114643	0.032*
C7	0.314 (2)	0.5633 (5)	0.3106 (13)	0.024 (3)
Cl3	0.6239 (12)	0.7105 (3)	0.2630 (12)	0.0234 (15)	0.789 (19)
C8	0.482 (2)	0.6037 (6)	0.2695 (16)	0.021 (3)	0.789 (19)
H8	0.492135	0.604763	0.161014	0.025*	0.789 (19)
C9	0.440 (2)	0.6607 (7)	0.3256 (17)	0.024 (3)	0.789 (19)
H9	0.439660	0.660553	0.434561	0.028*	0.789 (19)
Br7	−0.00734 (19)	0.57685 (6)	0.83633 (16)	0.0335 (3)
Br8	0.5604 (2)	0.68245 (7)	0.77338 (19)	0.0435 (4)
O4	0.4649 (13)	0.5577 (4)	0.9451 (9)	0.0251 (18)
N4	0.4886 (16)	0.5309 (5)	0.7086 (10)	0.025 (2)
H4A	0.572139	0.503590	0.731030	0.030*
H4B	0.450995	0.536820	0.617012	0.030*
C10	0.420 (2)	0.5629 (5)	0.8122 (14)	0.025 (2)
Cl4	0.1061 (10)	0.7086 (3)	0.7369 (8)	0.0266 (11)	0.817 (19)
C11	0.251 (2)	0.6031 (6)	0.7628 (15)	0.024 (3)	0.817 (19)
H11	0.242368	0.604210	0.653755	0.029*	0.817 (19)
C12	0.287 (2)	0.6613 (6)	0.8207 (17)	0.024 (3)	0.817 (19)
H12	0.272943	0.661602	0.928967	0.029*	0.817 (19)
Cl1A	−0.430 (5)	0.3001 (15)	0.482 (4)	0.0318 (14)	0.210 (19)
Cl2A	1.166 (7)	0.2983 (18)	0.987 (6)	0.0261 (12)	0.14 (2)
Cl3A	0.656 (5)	0.7030 (15)	0.281 (5)	0.0234 (15)	0.211 (19)
Cl4A	0.060 (5)	0.6990 (12)	0.735 (4)	0.0266 (11)	0.183 (19)
C2A	−0.138 (5)	0.3804 (11)	0.500 (5)	0.022 (3)	0.210 (19)
H2A	−0.184800	0.385702	0.601368	0.027*	0.210 (19)
C3A	−0.311 (6)	0.3600 (13)	0.408 (5)	0.021 (3)	0.210 (19)
H3A	−0.263207	0.351038	0.308659	0.025*	0.210 (19)
C5A	0.874 (6)	0.3793 (13)	1.001 (7)	0.024 (3)	0.14 (2)
H5A	0.922076	0.383694	1.104545	0.028*	0.14 (2)
C6A	1.050 (7)	0.3599 (17)	0.912 (8)	0.024 (3)	0.14 (2)
H6A	0.999643	0.351779	0.810765	0.029*	0.14 (2)
C8A	0.377 (6)	0.6201 (12)	0.247 (5)	0.021 (3)	0.211 (19)
H8A	0.432675	0.615072	0.147455	0.025*	0.211 (19)
C9A	0.550 (6)	0.6410 (15)	0.358 (6)	0.024 (3)	0.211 (19)
H9A	0.496103	0.647886	0.456895	0.028*	0.211 (19)
C11A	0.361 (6)	0.6217 (12)	0.756 (6)	0.024 (3)	0.183 (19)
H11A	0.322757	0.618000	0.649814	0.029*	0.183 (19)
C12A	0.173 (6)	0.6409 (14)	0.833 (6)	0.024 (3)	0.183 (19)
H12A	0.210439	0.652250	0.934887	0.029*	0.183 (19)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0229 (6)	0.0304 (7)	0.0475 (8)	0.0031 (5)	0.0021 (5)	0.0092 (6)
Br2	0.0268 (6)	0.0326 (7)	0.0505 (8)	0.0044 (6)	0.0001 (5)	0.0080 (6)
O1	0.031 (4)	0.029 (5)	0.015 (4)	−0.003 (4)	0.002 (3)	−0.001 (3)
N1	0.031 (5)	0.024 (5)	0.013 (4)	−0.005 (4)	0.001 (4)	−0.002 (4)
C1	0.025 (6)	0.023 (6)	0.020 (5)	−0.005 (5)	0.003 (4)	−0.006 (4)
Cl1	0.027 (3)	0.020 (2)	0.048 (4)	−0.006 (2)	−0.002 (2)	0.006 (2)
C2	0.023 (8)	0.029 (9)	0.016 (6)	−0.003 (6)	0.008 (6)	−0.004 (6)
C3	0.021 (7)	0.028 (8)	0.013 (6)	−0.002 (6)	−0.007 (5)	0.003 (5)
Br3	0.0230 (6)	0.0305 (7)	0.0487 (8)	−0.0015 (5)	0.0031 (5)	0.0072 (6)
Br4	0.0294 (7)	0.0365 (8)	0.0545 (9)	−0.0023 (6)	0.0013 (6)	0.0026 (7)
O2	0.029 (4)	0.024 (5)	0.020 (4)	0.003 (3)	0.002 (3)	−0.006 (3)
N2	0.024 (5)	0.026 (5)	0.015 (4)	0.002 (4)	0.003 (4)	−0.007 (4)
C4	0.025 (5)	0.017 (6)	0.027 (6)	0.003 (5)	−0.005 (4)	0.004 (4)
Cl2	0.022 (3)	0.017 (3)	0.040 (2)	0.0054 (17)	0.000 (2)	−0.0030 (19)
C5	0.028 (7)	0.025 (7)	0.017 (6)	0.008 (6)	−0.003 (5)	0.002 (5)
C6	0.021 (6)	0.022 (7)	0.030 (7)	0.000 (5)	0.005 (5)	−0.004 (6)
Br5	0.0238 (6)	0.0314 (7)	0.0533 (8)	0.0038 (5)	0.0029 (5)	0.0106 (7)
Br6	0.0295 (7)	0.0380 (8)	0.0538 (9)	0.0035 (6)	−0.0003 (6)	0.0093 (7)
O3	0.028 (4)	0.027 (5)	0.014 (4)	−0.007 (4)	0.001 (3)	−0.001 (3)
N3	0.025 (5)	0.034 (6)	0.019 (5)	−0.001 (4)	−0.003 (4)	0.004 (4)
C7	0.030 (6)	0.026 (6)	0.016 (5)	−0.003 (5)	−0.001 (4)	0.000 (4)
Cl3	0.018 (3)	0.008 (3)	0.045 (4)	−0.002 (2)	0.010 (3)	0.000 (2)
C8	0.018 (7)	0.025 (8)	0.020 (6)	0.000 (6)	−0.003 (5)	0.001 (5)
C9	0.022 (7)	0.022 (7)	0.027 (7)	0.002 (6)	0.003 (6)	−0.005 (6)
Br7	0.0243 (6)	0.0284 (7)	0.0477 (7)	−0.0020 (5)	0.0020 (5)	0.0037 (6)
Br8	0.0304 (7)	0.0382 (8)	0.0618 (10)	−0.0032 (6)	0.0002 (6)	0.0104 (7)
O4	0.032 (5)	0.029 (5)	0.014 (4)	0.002 (4)	0.002 (3)	0.000 (3)
N4	0.029 (5)	0.033 (6)	0.014 (4)	0.002 (5)	0.002 (4)	0.001 (4)
C10	0.029 (6)	0.021 (6)	0.025 (6)	−0.002 (5)	−0.002 (5)	−0.001 (5)
Cl4	0.021 (3)	0.011 (2)	0.0485 (19)	0.0031 (18)	0.005 (2)	0.002 (2)
C11	0.033 (8)	0.024 (8)	0.017 (6)	−0.005 (6)	0.004 (6)	−0.001 (5)
C12	0.019 (6)	0.027 (8)	0.028 (7)	−0.010 (5)	0.004 (5)	0.001 (6)
Cl1A	0.027 (3)	0.020 (2)	0.048 (4)	−0.006 (2)	−0.002 (2)	0.006 (2)
Cl2A	0.022 (3)	0.017 (3)	0.040 (2)	0.0054 (17)	0.000 (2)	−0.0030 (19)
Cl3A	0.018 (3)	0.008 (3)	0.045 (4)	−0.002 (2)	0.010 (3)	0.000 (2)
Cl4A	0.021 (3)	0.011 (2)	0.0485 (19)	0.0031 (18)	0.005 (2)	0.002 (2)
C2A	0.023 (8)	0.029 (9)	0.016 (6)	−0.003 (6)	0.008 (6)	−0.004 (6)
C3A	0.021 (7)	0.028 (8)	0.013 (6)	−0.002 (6)	−0.007 (5)	0.003 (5)
C5A	0.028 (7)	0.025 (7)	0.017 (6)	0.008 (6)	−0.003 (5)	0.002 (5)
C6A	0.021 (6)	0.022 (7)	0.030 (7)	0.000 (5)	0.005 (5)	−0.004 (6)
C8A	0.018 (7)	0.025 (8)	0.020 (6)	0.000 (6)	−0.003 (5)	0.001 (5)
C9A	0.022 (7)	0.022 (7)	0.027 (7)	0.002 (6)	0.003 (6)	−0.005 (6)
C11A	0.033 (8)	0.024 (8)	0.017 (6)	−0.005 (6)	0.004 (6)	−0.001 (5)
C12A	0.019 (6)	0.027 (8)	0.028 (7)	−0.010 (5)	0.004 (5)	0.001 (6)

Geometric parameters (Å, º) top

Br1—C2	1.997 (16)	C7—C8	1.533 (19)
Br1—C3A	2.00 (3)	C7—C8A	1.56 (3)
Br2—C3	1.944 (14)	Cl3—C9	1.813 (16)
Br2—C2A	1.99 (3)	C8—H8	1.0000
O1—C1	1.256 (14)	C8—C9	1.50 (2)
N1—H1A	0.8800	C9—H9	1.0000
N1—H1B	0.8800	Br7—C11	1.961 (15)
N1—C1	1.338 (15)	Br7—C12A	1.95 (3)
C1—C2	1.519 (18)	Br8—C12	1.939 (14)
C1—C2A	1.55 (3)	Br8—C11A	1.97 (3)
Cl1—C3	1.789 (15)	O4—C10	1.251 (15)
C2—H2	1.0000	N4—H4A	0.8800
C2—C3	1.49 (2)	N4—H4B	0.8800
C3—H3	1.0000	N4—C10	1.317 (16)
Br3—C5	1.965 (15)	C10—C11	1.54 (2)
Br3—C6A	1.97 (3)	C10—C11A	1.56 (3)
Br4—C6	1.946 (14)	Cl4—C12	1.806 (16)
Br4—C5A	1.97 (3)	C11—H11	1.0000
O2—C4	1.243 (14)	C11—C12	1.519 (19)
N2—H2B	0.8800	C12—H12	1.0000
N2—H2C	0.8800	Cl1A—C3A	1.79 (3)
N2—C4	1.324 (15)	Cl2A—C6A	1.80 (3)
C4—C5	1.533 (17)	Cl3A—C9A	1.81 (3)
C4—C5A	1.56 (3)	Cl4A—C12A	1.81 (3)
Cl2—C6	1.793 (15)	C2A—H2A	1.0000
C5—H5	1.0000	C2A—C3A	1.48 (3)
C5—C6	1.509 (19)	C3A—H3A	1.0000
C6—H6	1.0000	C5A—H5A	1.0000
Br5—C8	1.964 (15)	C5A—C6A	1.52 (3)
Br5—C9A	1.96 (3)	C6A—H6A	1.0000
Br6—C9	1.961 (15)	C8A—H8A	1.0000
Br6—C8A	2.00 (3)	C8A—C9A	1.59 (7)
O3—C7	1.240 (15)	C9A—H9A	1.0000
N3—H3B	0.8800	C11A—H11A	1.0000
N3—H3C	0.8800	C11A—C12A	1.52 (3)
N3—C7	1.333 (16)	C12A—H12A	1.0000

H1A—N1—H1B	120.0	O4—C10—C11	119.8 (11)
C1—N1—H1A	120.0	O4—C10—C11A	118 (2)
C1—N1—H1B	120.0	N4—C10—C11	115.0 (11)
O1—C1—N1	122.0 (11)	N4—C10—C11A	113 (2)
O1—C1—C2	121.6 (11)	Br7—C11—H11	109.2
O1—C1—C2A	119.0 (19)	C10—C11—Br7	108.8 (9)
N1—C1—C2	116.3 (10)	C10—C11—H11	109.2
N1—C1—C2A	112.2 (19)	C12—C11—Br7	107.8 (9)
Br1—C2—H2	109.8	C12—C11—C10	112.5 (12)
C1—C2—Br1	107.0 (10)	C12—C11—H11	109.2
C1—C2—H2	109.8	Br8—C12—H12	109.7
C3—C2—Br1	107.6 (10)	Cl4—C12—Br8	110.1 (8)
C3—C2—C1	112.8 (11)	Cl4—C12—H12	109.7
C3—C2—H2	109.8	C11—C12—Br8	107.5 (10)
Br2—C3—H3	110.5	C11—C12—Cl4	110.2 (10)
Cl1—C3—Br2	109.9 (8)	C11—C12—H12	109.7
Cl1—C3—H3	110.5	Br2—C2A—H2A	108.2
C2—C3—Br2	106.3 (10)	C1—C2A—Br2	119 (2)
C2—C3—Cl1	108.9 (10)	C1—C2A—H2A	108.2
C2—C3—H3	110.5	C3A—C2A—Br2	105 (2)
H2B—N2—H2C	120.0	C3A—C2A—C1	107 (3)
C4—N2—H2B	120.0	C3A—C2A—H2A	108.2
C4—N2—H2C	120.0	Br1—C3A—H3A	109.0
O2—C4—N2	122.7 (11)	Cl1A—C3A—Br1	112 (2)
O2—C4—C5	120.2 (11)	Cl1A—C3A—H3A	109.0
O2—C4—C5A	120 (3)	C2A—C3A—Br1	105 (2)
N2—C4—C5	117.1 (11)	C2A—C3A—Cl1A	113 (3)
N2—C4—C5A	109 (3)	C2A—C3A—H3A	109.0
Br3—C5—H5	110.0	Br4—C5A—H5A	108.3
C4—C5—Br3	106.6 (9)	C4—C5A—Br4	121 (2)
C4—C5—H5	110.0	C4—C5A—H5A	108.3
C6—C5—Br3	109.1 (9)	C6A—C5A—Br4	106 (3)
C6—C5—C4	111.0 (11)	C6A—C5A—C4	104 (3)
C6—C5—H5	110.0	C6A—C5A—H5A	108.3
Br4—C6—H6	110.0	Br3—C6A—H6A	108.6
Cl2—C6—Br4	110.4 (8)	Cl2A—C6A—Br3	113 (3)
Cl2—C6—H6	110.0	Cl2A—C6A—H6A	108.6
C5—C6—Br4	105.8 (9)	C5A—C6A—Br3	106 (3)
C5—C6—Cl2	110.7 (10)	C5A—C6A—Cl2A	112 (4)
C5—C6—H6	110.0	C5A—C6A—H6A	108.6
H3B—N3—H3C	120.0	Br6—C8A—H8A	110.3
C7—N3—H3B	120.0	C7—C8A—Br6	118 (2)
C7—N3—H3C	120.0	C7—C8A—H8A	110.3
O3—C7—N3	122.7 (12)	C7—C8A—C9A	104 (3)
O3—C7—C8	120.2 (11)	C9A—C8A—Br6	104 (2)
O3—C7—C8A	122 (2)	C9A—C8A—H8A	110.3
N3—C7—C8	116.6 (11)	Br5—C9A—H9A	111.7
N3—C7—C8A	111 (2)	Cl3A—C9A—Br5	113 (2)
Br5—C8—H8	109.6	Cl3A—C9A—H9A	111.7
C7—C8—Br5	108.9 (9)	C8A—C9A—Br5	102 (2)
C7—C8—H8	109.6	C8A—C9A—Cl3A	107 (3)
C9—C8—Br5	107.8 (9)	C8A—C9A—H9A	111.7
C9—C8—C7	111.2 (12)	Br8—C11A—H11A	107.0
C9—C8—H8	109.6	C10—C11A—Br8	120 (2)
Br6—C9—H9	110.2	C10—C11A—H11A	107.0
Cl3—C9—Br6	108.5 (8)	C12A—C11A—Br8	107 (2)
Cl3—C9—H9	110.2	C12A—C11A—C10	109 (3)
C8—C9—Br6	105.8 (10)	C12A—C11A—H11A	107.0
C8—C9—Cl3	111.8 (10)	Br7—C12A—H12A	109.6
C8—C9—H9	110.2	Cl4A—C12A—Br7	113 (2)
H4A—N4—H4B	120.0	Cl4A—C12A—H12A	109.6
C10—N4—H4A	120.0	C11A—C12A—Br7	106 (2)
C10—N4—H4B	120.0	C11A—C12A—Cl4A	109 (3)
O4—C10—N4	124.6 (12)	C11A—C12A—H12A	109.6

Br1—C2—C3—Br2	172.7 (6)	Br5—C8—C9—Br6	−175.7 (7)
Br1—C2—C3—Cl1	−68.9 (10)	Br5—C8—C9—Cl3	66.3 (12)
Br2—C2A—C3A—Br1	−175.6 (18)	Br6—C8A—C9A—Br5	178.3 (18)
Br2—C2A—C3A—Cl1A	62 (3)	Br6—C8A—C9A—Cl3A	−63 (3)
O1—C1—C2—Br1	−67.0 (14)	O3—C7—C8—Br5	64.4 (15)
O1—C1—C2—C3	51.2 (17)	O3—C7—C8—C9	−54.2 (17)
O1—C1—C2A—Br2	61 (3)	O3—C7—C8A—Br6	−62 (4)
O1—C1—C2A—C3A	−59 (3)	O3—C7—C8A—C9A	52 (3)
N1—C1—C2—Br1	109.0 (11)	N3—C7—C8—Br5	−107.4 (11)
N1—C1—C2—C3	−132.8 (12)	N3—C7—C8—C9	133.9 (13)
N1—C1—C2A—Br2	−91 (3)	N3—C7—C8A—Br6	94 (3)
N1—C1—C2A—C3A	149 (2)	N3—C7—C8A—C9A	−152 (2)
C1—C2—C3—Br2	54.9 (13)	C7—C8—C9—Br6	−56.4 (13)
C1—C2—C3—Cl1	173.3 (10)	C7—C8—C9—Cl3	−174.4 (10)
C1—C2A—C3A—Br1	−48 (3)	C7—C8A—C9A—Br5	55 (3)
C1—C2A—C3A—Cl1A	−169 (3)	C7—C8A—C9A—Cl3A	173 (2)
Br3—C5—C6—Br4	−176.1 (6)	Br7—C11—C12—Br8	171.2 (7)
Br3—C5—C6—Cl2	64.3 (11)	Br7—C11—C12—Cl4	−68.8 (11)
Br4—C5A—C6A—Br3	175 (3)	Br8—C11A—C12A—Br7	−173 (2)
Br4—C5A—C6A—Cl2A	−61 (4)	Br8—C11A—C12A—Cl4A	66 (3)
O2—C4—C5—Br3	67.9 (13)	O4—C10—C11—Br7	−64.9 (14)
O2—C4—C5—C6	−50.7 (16)	O4—C10—C11—C12	54.4 (17)
O2—C4—C5A—Br4	−58 (5)	O4—C10—C11A—Br8	61 (4)
O2—C4—C5A—C6A	61 (4)	O4—C10—C11A—C12A	−62 (3)
N2—C4—C5—Br3	−109.0 (11)	N4—C10—C11—Br7	106.6 (11)
N2—C4—C5—C6	132.3 (12)	N4—C10—C11—C12	−134.1 (12)
N2—C4—C5A—Br4	92 (4)	N4—C10—C11A—Br8	−94 (3)
N2—C4—C5A—C6A	−149 (3)	N4—C10—C11A—C12A	143 (3)
C4—C5—C6—Br4	−59.0 (12)	C10—C11—C12—Br8	51.3 (13)
C4—C5—C6—Cl2	−178.6 (10)	C10—C11—C12—Cl4	171.2 (10)
C4—C5A—C6A—Br3	46 (4)	C10—C11A—C12A—Br7	−42 (4)
C4—C5A—C6A—Cl2A	170 (3)	C10—C11A—C12A—Cl4A	−164 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3	0.88	2.06	2.932 (13)	170
N1—H1B···O2ⁱ	0.88	2.14	2.974 (13)	157
C2—H2···O2ⁱ	1.00	2.25	3.154 (16)	150
N2—H2B···O4	0.88	2.09	2.968 (14)	173
N2—H2C···O1ⁱⁱ	0.88	2.06	2.896 (13)	159
C5—H5···O1ⁱⁱ	1.00	2.32	3.189 (16)	145
N3—H3B···O1	0.88	2.09	2.962 (14)	171
N3—H3C···O4ⁱⁱⁱ	0.88	2.09	2.920 (13)	158
C8—H8···O4ⁱⁱⁱ	1.00	2.29	3.175 (17)	147
N4—H4A···O2	0.88	2.07	2.944 (14)	174
N4—H4B···O3	0.88	2.06	2.902 (13)	159
C11—H11···O3	1.00	2.27	3.161 (16)	148
C2A—H2A···O2ⁱ	1.00	2.37	3.28 (4)	150
C5A—H5A···O1ⁱⁱ	1.00	2.35	3.25 (6)	149
C8A—H8A···O4ⁱⁱⁱ	1.00	2.33	3.22 (5)	147
C11A—H11A···O3	1.00	2.43	3.32 (5)	148

Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z+1; (iii) x, y, z−1.

rac-5-(1,2-Dibromo-2-phenylethyl)-1,3,4-oxathiazol-2-one (3) top

Crystal data top

C₁₀H₇Br₂NO₂S	D_x = 2.118 Mg m⁻³
M_r = 365.05	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca2₁	Cell parameters from 9932 reflections
a = 7.1195 (2) Å	θ = 3.1–35.0°
b = 16.4402 (5) Å	µ = 7.24 mm⁻¹
c = 9.7821 (3) Å	T = 100 K
V = 1144.96 (6) Å³	Rect. Prism, colourless
Z = 4	0.21 × 0.13 × 0.07 mm
F(000) = 704

Data collection top

Bruker D8 Venture diffractometer	5019 independent reflections
Radiation source: microfocus sealed tube, Incoatec IµS 3.0	4815 reflections with I > 2σ(I)
Multilayer mirror monochromator	R_int = 0.036
Detector resolution: 7.3910 pixels mm^-1	θ_max = 35.0°, θ_min = 3.1°
φ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −26→26
T_min = 0.448, T_max = 0.747	l = −15→15
43632 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.016	w = 1/[σ²(F_o²) + (0.0118P)² + 0.1534P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.036	(Δ/σ)_max = 0.001
S = 1.02	Δρ_max = 0.50 e Å⁻³
5019 reflections	Δρ_min = −0.38 e Å⁻³
255 parameters	Absolute structure: Refined as an inversion twin.
220 restraints	Absolute structure parameter: 0.040 (6)
Primary atom site location: dual

Special details top

Refinement. Refined as a 2-component inversion twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	0.5403 (2)	0.44452 (14)	0.7052 (2)	0.0175 (2)	0.883 (4)
O1	0.6961 (4)	0.50389 (19)	0.4757 (4)	0.0188 (4)	0.883 (4)
O2	0.5069 (4)	0.39365 (17)	0.4616 (3)	0.0132 (4)	0.883 (4)
N1	0.4023 (6)	0.3619 (2)	0.6761 (3)	0.0164 (5)	0.883 (4)
C1	0.5980 (9)	0.4550 (4)	0.5332 (8)	0.0138 (6)	0.883 (4)
C2	0.4019 (3)	0.34742 (13)	0.5477 (3)	0.0132 (3)	0.883 (4)
C3	0.2979 (3)	0.28028 (11)	0.4789 (2)	0.0132 (4)	0.883 (4)
H3	0.244025	0.300427	0.390774	0.016*	0.883 (4)
C4	0.1438 (3)	0.24127 (11)	0.5639 (2)	0.0135 (4)	0.883 (4)
H4	0.199608	0.222492	0.652272	0.016*	0.883 (4)
C5	0.0473 (4)	0.17027 (15)	0.4973 (3)	0.0142 (4)	0.883 (4)
C6	−0.0196 (5)	0.17478 (18)	0.3631 (3)	0.0178 (4)	0.883 (4)
H6	−0.001018	0.222897	0.311082	0.021*	0.883 (4)
C7	−0.1133 (7)	0.1089 (2)	0.3058 (3)	0.0185 (5)	0.883 (4)
H7	−0.157368	0.111968	0.214316	0.022*	0.883 (4)
C8	−0.1428 (6)	0.0386 (2)	0.3819 (4)	0.0190 (7)	0.883 (4)
H8	−0.209045	−0.005880	0.343064	0.023*	0.883 (4)
C9	−0.0755 (4)	0.03364 (15)	0.5142 (3)	0.0189 (4)	0.883 (4)
H9	−0.094743	−0.014537	0.565951	0.023*	0.883 (4)
C10	0.0207 (4)	0.09914 (16)	0.5720 (3)	0.0154 (4)	0.883 (4)
H10	0.068150	0.095154	0.662506	0.019*	0.883 (4)
Br1	0.48888 (7)	0.19548 (4)	0.44095 (6)	0.01456 (9)	0.883 (4)
Br2	−0.04519 (14)	0.32648 (7)	0.60411 (7)	0.01761 (10)	0.883 (4)
Br2A	−0.0407 (14)	0.3295 (6)	0.5833 (17)	0.042 (3)	0.117 (4)
S1A	0.564 (2)	0.4441 (12)	0.715 (2)	0.0175 (2)	0.117 (4)
N1A	0.418 (6)	0.368 (2)	0.708 (3)	0.024 (5)	0.117 (4)
C1A	0.581 (8)	0.447 (4)	0.525 (7)	0.0138 (6)	0.117 (4)
C2A	0.416 (2)	0.3401 (10)	0.595 (2)	0.0132 (3)	0.117 (4)
O1A	0.658 (4)	0.4908 (17)	0.460 (3)	0.026 (4)	0.117 (4)
O2A	0.483 (4)	0.3799 (17)	0.485 (2)	0.020 (4)	0.117 (4)
C3A	0.317 (2)	0.2561 (11)	0.5610 (16)	0.023 (3)	0.117 (4)
H3A	0.292963	0.226090	0.648124	0.027*	0.117 (4)
C4A	0.142 (2)	0.2646 (10)	0.4859 (17)	0.020 (3)	0.117 (4)
H4A	0.170813	0.292744	0.397623	0.024*	0.117 (4)
Br1A	0.4910 (10)	0.1916 (4)	0.4461 (16)	0.050 (2)	0.117 (4)
C6A	−0.035 (4)	0.1687 (13)	0.3235 (17)	0.029 (5)	0.117 (4)
H6A	−0.027058	0.209079	0.254259	0.034*	0.117 (4)
C5A	0.041 (3)	0.1836 (9)	0.4521 (18)	0.018 (3)	0.117 (4)
C10A	0.030 (3)	0.1246 (10)	0.5534 (15)	0.018 (3)	0.117 (4)
H10A	0.082035	0.134749	0.641244	0.021*	0.117 (4)
C9A	−0.057 (3)	0.0506 (9)	0.526 (2)	0.0189 (4)	0.117 (4)
H9A	−0.064045	0.010188	0.595481	0.023*	0.117 (4)
C8A	−0.132 (5)	0.0356 (13)	0.398 (3)	0.029 (7)	0.117 (4)
H8A	−0.191633	−0.014929	0.379108	0.035*	0.117 (4)
C7A	−0.121 (5)	0.0947 (16)	0.296 (2)	0.027 (6)	0.117 (4)
H7A	−0.173141	0.084516	0.208495	0.033*	0.117 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0180 (6)	0.0199 (2)	0.0146 (4)	−0.0042 (4)	−0.0026 (3)	−0.0035 (3)
O1	0.0169 (11)	0.0158 (11)	0.0237 (9)	−0.0061 (7)	0.0031 (9)	−0.0016 (8)
O2	0.0145 (9)	0.0116 (9)	0.0134 (11)	−0.0027 (6)	−0.0007 (7)	−0.0008 (7)
N1	0.0198 (10)	0.0133 (12)	0.0161 (13)	−0.0035 (8)	−0.0005 (11)	−0.0013 (10)
C1	0.0137 (16)	0.0109 (17)	0.0169 (14)	−0.0006 (10)	−0.0020 (11)	−0.0043 (11)
C2	0.0138 (7)	0.0115 (7)	0.0144 (9)	−0.0011 (6)	−0.0023 (7)	0.0009 (7)
C3	0.0137 (7)	0.0114 (7)	0.0146 (8)	0.0002 (6)	−0.0013 (6)	−0.0011 (6)
C4	0.0134 (7)	0.0112 (7)	0.0158 (9)	0.0002 (5)	−0.0011 (6)	0.0002 (6)
C5	0.0140 (8)	0.0122 (9)	0.0166 (10)	−0.0026 (7)	−0.0016 (9)	−0.0005 (8)
C6	0.0182 (10)	0.0162 (10)	0.0191 (11)	−0.0053 (7)	−0.0048 (10)	0.0004 (9)
C7	0.0153 (13)	0.0207 (13)	0.0194 (11)	−0.0043 (9)	−0.0025 (9)	−0.0041 (9)
C8	0.0145 (15)	0.0182 (16)	0.0243 (12)	−0.0043 (11)	0.0033 (10)	−0.0076 (11)
C9	0.0196 (10)	0.0115 (10)	0.0255 (10)	−0.0035 (8)	0.0054 (8)	−0.0033 (9)
C10	0.0180 (9)	0.0113 (10)	0.0170 (9)	−0.0011 (8)	0.0017 (7)	−0.0004 (8)
Br1	0.01267 (17)	0.01285 (18)	0.01815 (15)	0.00092 (14)	0.00122 (13)	−0.00465 (15)
Br2	0.01344 (17)	0.01324 (18)	0.02615 (19)	0.00243 (12)	0.00060 (14)	−0.00444 (12)
Br2A	0.026 (2)	0.024 (2)	0.077 (7)	0.0024 (14)	0.013 (3)	−0.008 (3)
S1A	0.0180 (6)	0.0199 (2)	0.0146 (4)	−0.0042 (4)	−0.0026 (3)	−0.0035 (3)
N1A	0.031 (12)	0.020 (9)	0.019 (8)	−0.014 (8)	0.007 (8)	−0.009 (7)
C1A	0.0137 (16)	0.0109 (17)	0.0169 (14)	−0.0006 (10)	−0.0020 (11)	−0.0043 (11)
C2A	0.0138 (7)	0.0115 (7)	0.0144 (9)	−0.0011 (6)	−0.0023 (7)	0.0009 (7)
O1A	0.025 (10)	0.020 (8)	0.034 (10)	−0.013 (5)	−0.003 (7)	−0.002 (6)
O2A	0.024 (8)	0.023 (8)	0.012 (7)	−0.009 (5)	0.001 (5)	−0.005 (5)
C3A	0.024 (6)	0.030 (7)	0.014 (6)	−0.010 (5)	0.003 (5)	−0.003 (6)
C4A	0.028 (7)	0.019 (6)	0.013 (6)	−0.002 (5)	0.004 (5)	−0.002 (5)
Br1A	0.034 (3)	0.020 (2)	0.096 (5)	0.0028 (18)	0.004 (3)	−0.004 (3)
C6A	0.025 (10)	0.036 (10)	0.024 (9)	0.000 (7)	−0.010 (9)	−0.005 (8)
C5A	0.018 (7)	0.014 (6)	0.022 (8)	−0.001 (4)	0.000 (8)	−0.001 (6)
C10A	0.016 (7)	0.015 (7)	0.021 (8)	−0.002 (6)	−0.002 (6)	−0.005 (6)
C9A	0.0196 (10)	0.0115 (10)	0.0255 (10)	−0.0035 (8)	0.0054 (8)	−0.0033 (9)
C8A	0.024 (16)	0.017 (12)	0.046 (10)	−0.001 (10)	0.004 (9)	−0.015 (9)
C7A	0.015 (10)	0.029 (11)	0.038 (10)	−0.005 (8)	−0.006 (8)	−0.021 (7)

Geometric parameters (Å, º) top

S1—N1	1.701 (4)	Br2A—C4A	1.93 (2)
S1—C1	1.741 (9)	S1A—N1A	1.62 (4)
O1—C1	1.204 (7)	S1A—C1A	1.86 (7)
O2—C1	1.388 (5)	N1A—C2A	1.20 (3)
O2—C2	1.358 (3)	C1A—O1A	1.10 (6)
N1—C2	1.278 (3)	C1A—O2A	1.36 (5)
C2—C3	1.490 (3)	C2A—O2A	1.35 (3)
C3—H3	1.0000	C2A—C3A	1.58 (2)
C3—C4	1.519 (3)	C3A—H3A	1.0000
C3—Br1	1.9822 (19)	C3A—C4A	1.45 (2)
C4—H4	1.0000	C3A—Br1A	1.98 (2)
C4—C5	1.503 (3)	C4A—H4A	1.0000
C4—Br2	1.982 (2)	C4A—C5A	1.55 (2)
C5—C6	1.398 (3)	C6A—H6A	0.9500
C5—C10	1.392 (3)	C6A—C5A	1.3900
C6—H6	0.9500	C6A—C7A	1.3900
C6—C7	1.389 (4)	C5A—C10A	1.3900
C7—H7	0.9500	C10A—H10A	0.9500
C7—C8	1.391 (4)	C10A—C9A	1.3900
C8—H8	0.9500	C9A—H9A	0.9500
C8—C9	1.382 (4)	C9A—C8A	1.3900
C9—H9	0.9500	C8A—H8A	0.9500
C9—C10	1.396 (3)	C8A—C7A	1.3900
C10—H10	0.9500	C7A—H7A	0.9500

N1—S1—C1	93.06 (19)	N1A—S1A—C1A	91.1 (19)
C2—O2—C1	110.6 (4)	C2A—N1A—S1A	110 (3)
C2—N1—S1	108.3 (3)	O1A—C1A—S1A	128 (4)
O1—C1—S1	130.8 (4)	O1A—C1A—O2A	128 (6)
O1—C1—O2	121.4 (6)	O2A—C1A—S1A	103 (4)
O2—C1—S1	107.8 (4)	N1A—C2A—O2A	123 (2)
O2—C2—C3	114.1 (2)	N1A—C2A—C3A	123 (2)
N1—C2—O2	120.3 (3)	O2A—C2A—C3A	114.4 (18)
N1—C2—C3	125.6 (3)	C2A—O2A—C1A	110 (4)
C2—C3—H3	109.6	C2A—C3A—H3A	109.2
C2—C3—C4	115.11 (16)	C2A—C3A—Br1A	108.1 (11)
C2—C3—Br1	105.36 (13)	C4A—C3A—C2A	113.6 (15)
C4—C3—H3	109.6	C4A—C3A—H3A	109.2
C4—C3—Br1	107.52 (12)	C4A—C3A—Br1A	107.4 (11)
Br1—C3—H3	109.6	Br1A—C3A—H3A	109.2
C3—C4—H4	108.5	Br2A—C4A—H4A	107.9
C3—C4—Br2	107.50 (13)	C3A—C4A—Br2A	112.4 (12)
C5—C4—C3	114.87 (17)	C3A—C4A—H4A	107.9
C5—C4—H4	108.5	C3A—C4A—C5A	115.1 (15)
C5—C4—Br2	108.95 (15)	C5A—C4A—Br2A	105.4 (12)
Br2—C4—H4	108.5	C5A—C4A—H4A	107.9
C6—C5—C4	121.4 (2)	C5A—C6A—H6A	120.0
C10—C5—C4	119.2 (2)	C5A—C6A—C7A	120.0
C10—C5—C6	119.4 (2)	C7A—C6A—H6A	120.0
C5—C6—H6	120.0	C6A—C5A—C4A	121.7 (13)
C7—C6—C5	120.1 (2)	C10A—C5A—C4A	118.3 (13)
C7—C6—H6	120.0	C10A—C5A—C6A	120.0
C6—C7—H7	119.9	C5A—C10A—H10A	120.0
C6—C7—C8	120.3 (3)	C5A—C10A—C9A	120.0
C8—C7—H7	119.9	C9A—C10A—H10A	120.0
C7—C8—H8	120.1	C10A—C9A—H9A	120.0
C9—C8—C7	119.9 (2)	C8A—C9A—C10A	120.0
C9—C8—H8	120.1	C8A—C9A—H9A	120.0
C8—C9—H9	119.9	C9A—C8A—H8A	120.0
C8—C9—C10	120.2 (2)	C9A—C8A—C7A	120.0
C10—C9—H9	119.9	C7A—C8A—H8A	120.0
C5—C10—C9	120.2 (2)	C6A—C7A—H7A	120.0
C5—C10—H10	119.9	C8A—C7A—C6A	120.0
C9—C10—H10	119.9	C8A—C7A—H7A	120.0

S1—N1—C2—O2	2.2 (4)	Br2A—C4A—C5A—C6A	100.0 (16)
S1—N1—C2—C3	−179.85 (19)	Br2A—C4A—C5A—C10A	−81.2 (15)
O2—C2—C3—C4	−165.4 (2)	S1A—N1A—C2A—O2A	−17 (4)
O2—C2—C3—Br1	76.3 (2)	S1A—N1A—C2A—C3A	168.4 (18)
N1—S1—C1—O1	179.7 (7)	S1A—C1A—O2A—C2A	0 (5)
N1—S1—C1—O2	0.0 (5)	N1A—S1A—C1A—O1A	176 (7)
N1—C2—C3—C4	16.5 (4)	N1A—S1A—C1A—O2A	−7 (4)
N1—C2—C3—Br1	−101.7 (3)	N1A—C2A—O2A—C1A	11 (5)
C1—S1—N1—C2	−1.2 (4)	N1A—C2A—C3A—C4A	107 (3)
C1—O2—C2—N1	−2.2 (5)	N1A—C2A—C3A—Br1A	−134 (3)
C1—O2—C2—C3	179.6 (4)	C1A—S1A—N1A—C2A	13 (4)
C2—O2—C1—S1	1.1 (6)	C2A—C3A—C4A—Br2A	−58.7 (17)
C2—O2—C1—O1	−178.7 (6)	C2A—C3A—C4A—C5A	−179.4 (14)
C2—C3—C4—C5	−176.43 (18)	O1A—C1A—O2A—C2A	177 (6)
C2—C3—C4—Br2	62.15 (19)	O2A—C2A—C3A—C4A	−68 (2)
C3—C4—C5—C6	−48.8 (3)	O2A—C2A—C3A—Br1A	51 (2)
C3—C4—C5—C10	132.5 (2)	C3A—C2A—O2A—C1A	−174 (3)
C4—C5—C6—C7	−178.0 (3)	C3A—C4A—C5A—C6A	−135.6 (16)
C4—C5—C10—C9	177.3 (2)	C3A—C4A—C5A—C10A	43.3 (19)
C5—C6—C7—C8	0.7 (4)	C4A—C5A—C10A—C9A	−178.9 (19)
C6—C5—C10—C9	−1.4 (3)	Br1A—C3A—C4A—Br2A	−178.3 (9)
C6—C7—C8—C9	−1.2 (4)	Br1A—C3A—C4A—C5A	61.0 (16)
C7—C8—C9—C10	0.5 (4)	C6A—C5A—C10A—C9A	0.0
C8—C9—C10—C5	0.8 (3)	C5A—C6A—C7A—C8A	0.0
C10—C5—C6—C7	0.6 (4)	C5A—C10A—C9A—C8A	0.0
Br1—C3—C4—C5	−59.39 (19)	C10A—C9A—C8A—C7A	0.0
Br1—C3—C4—Br2	179.19 (9)	C9A—C8A—C7A—C6A	0.0
Br2—C4—C5—C6	71.8 (3)	C7A—C6A—C5A—C4A	178.9 (19)
Br2—C4—C5—C10	−106.8 (2)	C7A—C6A—C5A—C10A	0.0

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···N1ⁱ	1.00	2.55	3.550 (4)	175
C6—H6···N1ⁱ	0.95	2.73	3.675 (5)	173
C4A—H4A···N1Aⁱ	1.00	2.32	3.24 (4)	152
C6A—H6A···N1Aⁱ	0.95	2.77	3.57 (5)	143

Symmetry code: (i) −x+1/2, y, z−1/2.

Bond lengths (Å) in known 1,3,4-oxathiazol-2-one structures top

CSD refcode	Fragment	N═C—C (Å)	C—C Hybridization	O═C—O (Å)	N═C—O (Å)	C═N (Å)	N—S (Å)	S—C (Å)	C═O (Å)
CEDGUO	1	1.49 (4)	sp²–sp³	1.384 (3)	1.366 (3)	1.262 (3)	1.690 (2)	1.752 (3)	1.188 (3)
GEHZEB	1	1.443 (2)	sp²–sp²	1.385 (2)	1.368 (2)	1.276 (2)	1.676 (1)	1.738 (2)	1.186 (2)
HEMYON	1	1.491 (5)	sp²–sp³	1.392 (5)	1.377 (5)	1.272 (5)	1.697 (3)	1.750 (4)	1.188 (6)
JELVUU	1	1.447 (3)	sp²–sp²	1.385 (3)	1.361 (2)	1.278 (3)	1.679 (2)	1.746 (2)	1.187 (3)
JELVUU	2	1.449 (3)	sp²–sp²	1.391 (2)	1.364 (2)	1.271 (3)	1.684 (2)	1.761 (2)	1.186 (2)
JELWAB	1	1.451 (2)	sp²–sp²	1.385 (2)	1.375 (1)	1.277 (2)	1.682 (1)	1.746 (1)	1.192 (2)
OPIROV	1	1.440 (5)	sp²–sp²	1.416 (5)	1.383 (4)	1.292 (5)	1.734 (4)	1.713 (4)	1.215 (5)
OPIRUB	1	1.434 (6)	sp²–sp²	1.421 (9)	1.465 (7)	1.286 (7)	1.736 (6)	1.802 (7)	1.119 (7)
OPISAI	1	1.461 (5)	sp²–sp²	1.400 (5)	1.422 (4)	1.237 (4)	1.711 (2)	1.733 (4)	1.177 (5)
OPISEM	1	1.41 (1)	sp²–sp²	1.376 (8)	1.373 (8)	1.280 (8)	1.705 (7)	1.736 (5)	1.233 (7)
TUHVAT	1	1.436 (8)	sp²–sp²	1.349 (8)	1.436 (8)	1.272 (9)	1.656 (5)	1.718 (7)	1.214 (8)
ZARBOJ	1	1.500 (4)	sp²–sp³	1.391 (3)	1.379 (2)	1.276 (3)	1.694 (2)	1.756 (3)	1.184 (3)
ZARBOJ	2	1.499 (4)	sp²–sp³	1.380(*)	1.377 (3)	1.269 (3)	1.697 (3)	1.762 (3)	1.186 (4)
ZARBUP	1	1.499 (3)	sp²–sp³	1.396 (3)	1.375 (3)	1.274 (3)	1.692 (2)	1.754 (2)	1.174 (3)
ZIZFET	1	1.457 (6)	sp²–sp²	1.380 (6)	1.379 (6)	1.268 (6)	1.683 (4)	1.754 (5)	1.188 (7)
ZIZFET	2	1.463 (7)	sp²–sp²	1.388 (6)	1.380 (6)	1.266 (5)	1.677 (4)	1.751 (5)	1.184 (6)
(1)	1 (of 6)	1.445 (6)	sp²–sp²	1.398 (5)	1.379 (6)	1.276 (6)	1.688 (4)	1.757 (5)	1.187 (5)
(3)	1	1.490 (3)	sp²–sp³	1.388 (5)	1.358 (3)	1.278 (3)	1.701 (4)	1.741 (9)	1.204 (7)

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Synthesis and crystal structures of halogenated oxa­thia­zolones and an unexpected pro­pan­amide

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Synthesis and crystal structures of halogenated oxathiazolones and an unexpected propanamide