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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229623002152/dv3021sup1.cif
Contains datablocks 1, 2, 3, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229623002152/dv30211sup2.hkl
Contains datablock 1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229623002152/dv30212sup3.hkl
Contains datablock 2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229623002152/dv30213sup4.hkl
Contains datablock 3

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229623002152/dv30211sup5.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229623002152/dv30212sup6.cml
Supplementary material

cml

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
C4H2ClNO2SF(000) = 984
Mr = 163.58Dx = 1.796 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 9.7839 (11) ÅCell parameters from 5075 reflections
b = 10.2313 (11) Åθ = 2.3–28.6°
c = 18.272 (2) ŵ = 0.89 mm1
β = 97.125 (1)°T = 125 K
V = 1814.9 (3) Å3Block, colourless
Z = 120.11 × 0.09 × 0.09 mm
Data collection top
Bruker D8 Venture
diffractometer
9072 independent reflections
Radiation source: microfocus sealed tube, Incoatec IµS 3.07423 reflections with I > 2σ(I)
Multilayer mirror monochromatorRint = 0.032
Detector resolution: 7.3910 pixels mm-1θmax = 29.2°, θmin = 1.1°
φ and ω scansh = 1213
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
k = 1313
Tmin = 0.703, Tmax = 0.746l = 2424
23045 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.036 w = 1/[σ2(Fo2) + (0.0356P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.085(Δ/σ)max = 0.001
S = 1.05Δρmax = 0.36 e Å3
9072 reflectionsΔρmin = 0.41 e Å3
488 parametersAbsolute structure: Refined as an inversion twin.
1 restraintAbsolute 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
xyzUiso*/Ueq
Cl10.21183 (12)0.71322 (13)0.50527 (6)0.0272 (3)
S10.13355 (12)0.80145 (12)0.16277 (7)0.0199 (3)
O10.1665 (3)0.6455 (3)0.26784 (16)0.0185 (7)
O20.1639 (3)0.5395 (4)0.15982 (16)0.0260 (7)
N10.1388 (4)0.8640 (4)0.2479 (2)0.0207 (9)
C10.1567 (4)0.6404 (5)0.1922 (2)0.0194 (9)
C20.1565 (5)0.7725 (5)0.2932 (3)0.0201 (11)
C30.1679 (4)0.7917 (5)0.3706 (2)0.0210 (10)
H30.1550020.8767110.3911160.025*
C40.1961 (4)0.6932 (5)0.4136 (2)0.0214 (10)
H40.2080590.6082740.3926930.026*
Cl60.82218 (12)0.53332 (12)1.00683 (6)0.0260 (3)
S60.86351 (11)0.43606 (11)0.66067 (6)0.0199 (3)
O110.8409 (3)0.5930 (3)0.76582 (16)0.0187 (7)
O120.8424 (3)0.6988 (3)0.65762 (15)0.0269 (8)
N60.8600 (4)0.3741 (4)0.7462 (2)0.0199 (9)
C210.8465 (4)0.5978 (5)0.6899 (2)0.0174 (9)
C220.8491 (4)0.4672 (5)0.7917 (3)0.0157 (10)
C230.8442 (4)0.4512 (5)0.8703 (2)0.0183 (10)
H230.8510580.3658810.8909430.022*
C240.8303 (4)0.5529 (5)0.9140 (2)0.0202 (10)
H240.8248010.6383570.8935240.024*
Cl50.50105 (12)0.46063 (14)0.67119 (6)0.0272 (3)
S50.54187 (11)0.55865 (12)0.32488 (6)0.0212 (3)
O90.4957 (3)0.4039 (3)0.42791 (18)0.0198 (8)
O100.4708 (3)0.3044 (3)0.31701 (16)0.0271 (8)
N50.5544 (4)0.6172 (4)0.41198 (19)0.0216 (8)
C170.4969 (4)0.4021 (5)0.3515 (2)0.0205 (10)
C180.5278 (4)0.5271 (5)0.4562 (3)0.0197 (11)
C190.5296 (4)0.5427 (5)0.5348 (2)0.0209 (10)
H190.5508340.6258870.5563380.025*
C200.5023 (4)0.4440 (5)0.5780 (2)0.0194 (10)
H200.4827600.3606840.5562800.023*
Cl20.52737 (13)0.29244 (13)0.17200 (6)0.0306 (3)
S20.49491 (12)0.19247 (11)0.17457 (6)0.0201 (3)
O30.5245 (3)0.3491 (3)0.06980 (16)0.0187 (7)
O40.5267 (3)0.4556 (4)0.17784 (16)0.0270 (7)
N20.4953 (4)0.1310 (4)0.08869 (19)0.0215 (9)
C50.5175 (4)0.3543 (4)0.1450 (2)0.0179 (9)
C60.5093 (4)0.2239 (5)0.0430 (2)0.0169 (10)
C70.5103 (4)0.2087 (5)0.0351 (2)0.0177 (10)
H70.4989810.1237870.0560970.021*
C80.5265 (4)0.3089 (6)0.0786 (2)0.0215 (10)
H80.5382200.3935620.0573780.026*
Cl30.17278 (12)0.54355 (13)0.33616 (6)0.0258 (3)
S30.19237 (12)0.43315 (11)0.01105 (6)0.0218 (3)
O50.1630 (3)0.5920 (3)0.09259 (17)0.0198 (8)
O60.1356 (3)0.6912 (3)0.01818 (16)0.0283 (8)
N30.2080 (4)0.3759 (4)0.0764 (2)0.0209 (9)
C90.1587 (4)0.5936 (5)0.0160 (2)0.0192 (10)
C100.1901 (4)0.4699 (5)0.1213 (3)0.0162 (10)
C110.1931 (4)0.4558 (5)0.2000 (2)0.0182 (9)
H110.2100380.3721810.2219050.022*
C120.1727 (4)0.5577 (5)0.2425 (2)0.0202 (10)
H120.1575290.6412100.2202590.024*
Cl40.83476 (13)0.69470 (13)0.16361 (6)0.0269 (3)
S40.83374 (12)0.80884 (11)0.51123 (7)0.0194 (3)
O70.8651 (3)0.6503 (3)0.40772 (15)0.0172 (7)
O80.8897 (3)0.5508 (3)0.51863 (15)0.0268 (7)
N40.8157 (4)0.8656 (4)0.4242 (2)0.0199 (9)
C130.8679 (4)0.6491 (5)0.4844 (2)0.0187 (9)
C140.8332 (4)0.7732 (5)0.3796 (3)0.0170 (11)
C150.8237 (4)0.7865 (5)0.3002 (2)0.0195 (10)
H150.8031480.8694260.2782370.023*
C160.8433 (4)0.6845 (5)0.2576 (2)0.0199 (10)
H160.8628830.6019810.2803480.024*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0328 (6)0.0339 (7)0.0153 (6)0.0039 (6)0.0041 (4)0.0000 (5)
S10.0261 (6)0.0177 (6)0.0161 (6)0.0009 (5)0.0040 (4)0.0020 (5)
O10.0234 (15)0.0150 (17)0.0170 (17)0.0005 (13)0.0021 (12)0.0011 (14)
O20.0349 (18)0.0196 (18)0.0236 (18)0.0008 (15)0.0045 (13)0.0052 (16)
N10.0262 (19)0.018 (2)0.018 (2)0.0004 (16)0.0039 (15)0.0008 (18)
C10.016 (2)0.023 (2)0.019 (2)0.0022 (17)0.0011 (16)0.0016 (19)
C20.020 (2)0.020 (3)0.021 (3)0.0021 (19)0.0028 (17)0.000 (2)
C30.026 (2)0.020 (3)0.017 (2)0.000 (2)0.0017 (17)0.002 (2)
C40.028 (2)0.023 (3)0.013 (2)0.001 (2)0.0015 (17)0.003 (2)
Cl60.0332 (6)0.0313 (7)0.0137 (5)0.0023 (6)0.0034 (4)0.0017 (5)
S60.0257 (6)0.0192 (6)0.0154 (6)0.0026 (5)0.0048 (4)0.0006 (5)
O110.0236 (16)0.0153 (18)0.0174 (18)0.0018 (13)0.0036 (13)0.0004 (14)
O120.0410 (19)0.0223 (19)0.0176 (16)0.0039 (14)0.0039 (13)0.0054 (14)
N60.0266 (19)0.018 (2)0.015 (2)0.0010 (16)0.0021 (14)0.0011 (17)
C210.0171 (19)0.021 (2)0.014 (2)0.0016 (17)0.0010 (16)0.0003 (19)
C220.017 (2)0.010 (3)0.019 (2)0.0020 (17)0.0007 (16)0.001 (2)
C230.020 (2)0.017 (2)0.017 (2)0.0007 (18)0.0002 (16)0.001 (2)
C240.024 (2)0.024 (3)0.012 (2)0.002 (2)0.0014 (16)0.001 (2)
Cl50.0298 (6)0.0383 (8)0.0137 (5)0.0049 (6)0.0039 (4)0.0012 (5)
S50.0266 (5)0.0219 (6)0.0151 (5)0.0061 (5)0.0023 (4)0.0012 (5)
O90.0262 (17)0.0176 (18)0.0158 (18)0.0032 (14)0.0030 (13)0.0001 (15)
O100.0400 (18)0.0217 (18)0.0199 (16)0.0055 (15)0.0056 (13)0.0042 (14)
N50.0260 (19)0.021 (2)0.0175 (19)0.0039 (16)0.0038 (15)0.0003 (16)
C170.023 (2)0.020 (2)0.019 (2)0.0024 (19)0.0041 (18)0.000 (2)
C180.016 (2)0.022 (3)0.021 (3)0.000 (2)0.0029 (18)0.001 (2)
C190.021 (2)0.022 (3)0.020 (2)0.001 (2)0.0031 (17)0.005 (2)
C200.019 (2)0.022 (3)0.017 (2)0.0010 (19)0.0012 (17)0.001 (2)
Cl20.0430 (7)0.0353 (8)0.0140 (5)0.0111 (6)0.0053 (5)0.0005 (5)
S20.0252 (6)0.0199 (7)0.0155 (6)0.0005 (5)0.0033 (4)0.0014 (5)
O30.0251 (15)0.0169 (17)0.0138 (16)0.0004 (13)0.0017 (12)0.0005 (13)
O40.0405 (19)0.0238 (18)0.0173 (16)0.0007 (15)0.0064 (13)0.0021 (15)
N20.030 (2)0.018 (2)0.016 (2)0.0010 (16)0.0034 (15)0.0000 (17)
C50.0180 (19)0.018 (2)0.017 (2)0.0007 (16)0.0008 (16)0.0026 (18)
C60.018 (2)0.017 (3)0.016 (2)0.0017 (19)0.0004 (16)0.001 (2)
C70.024 (2)0.013 (2)0.016 (2)0.0009 (19)0.0040 (17)0.002 (2)
C80.025 (2)0.025 (3)0.014 (2)0.004 (2)0.0005 (17)0.002 (2)
Cl30.0318 (6)0.0314 (7)0.0145 (5)0.0046 (5)0.0042 (4)0.0009 (5)
S30.0307 (6)0.0199 (7)0.0147 (6)0.0053 (5)0.0023 (4)0.0002 (5)
O50.0282 (16)0.0148 (18)0.0162 (18)0.0016 (13)0.0024 (13)0.0012 (14)
O60.0434 (19)0.0215 (19)0.0202 (17)0.0031 (15)0.0042 (13)0.0020 (15)
N30.030 (2)0.018 (2)0.014 (2)0.0056 (16)0.0001 (15)0.0005 (17)
C90.021 (2)0.021 (2)0.015 (2)0.0009 (18)0.0015 (16)0.0009 (19)
C100.018 (2)0.012 (3)0.018 (2)0.0022 (19)0.0012 (16)0.001 (2)
C110.022 (2)0.015 (2)0.018 (2)0.0011 (18)0.0052 (16)0.0007 (19)
C120.025 (2)0.022 (3)0.014 (2)0.000 (2)0.0019 (17)0.001 (2)
Cl40.0366 (6)0.0308 (7)0.0134 (5)0.0025 (5)0.0040 (4)0.0002 (5)
S40.0260 (6)0.0183 (6)0.0138 (6)0.0022 (5)0.0018 (4)0.0021 (5)
O70.0231 (15)0.0144 (16)0.0145 (16)0.0017 (12)0.0043 (11)0.0009 (13)
O80.0421 (18)0.0205 (18)0.0178 (15)0.0054 (15)0.0045 (13)0.0042 (15)
N40.0225 (18)0.021 (2)0.016 (2)0.0011 (16)0.0028 (14)0.0005 (17)
C130.017 (2)0.024 (2)0.015 (2)0.0005 (17)0.0036 (16)0.0024 (18)
C140.014 (2)0.019 (3)0.019 (3)0.0009 (18)0.0037 (16)0.003 (2)
C150.023 (2)0.020 (3)0.016 (2)0.0005 (19)0.0042 (17)0.006 (2)
C160.021 (2)0.026 (3)0.013 (2)0.001 (2)0.0028 (16)0.000 (2)
Geometric parameters (Å, º) top
Cl1—C41.714 (5)Cl2—C81.716 (5)
S1—N11.688 (4)S2—N21.691 (4)
S1—C11.757 (5)S2—C51.764 (5)
O1—C11.398 (5)O3—C51.385 (5)
O1—C21.379 (6)O3—C61.372 (6)
O2—C11.187 (5)O4—C51.195 (5)
N1—C21.276 (6)N2—C61.284 (6)
C2—C31.445 (6)C6—C71.438 (5)
C3—H30.9500C7—H70.9500
C3—C41.328 (6)C7—C81.319 (7)
C4—H40.9500C8—H80.9500
Cl6—C241.719 (4)Cl3—C121.717 (4)
S6—N61.692 (4)S3—N31.691 (4)
S6—C211.753 (5)S3—C91.757 (5)
O11—C211.396 (5)O5—C91.395 (5)
O11—C221.371 (5)O5—C101.368 (5)
O12—C211.188 (5)O6—C91.185 (6)
N6—C221.277 (6)N3—C101.291 (6)
C22—C231.451 (6)C10—C111.443 (6)
C23—H230.9500C11—H110.9500
C23—C241.329 (6)C11—C121.330 (6)
C24—H240.9500C12—H120.9500
Cl5—C201.713 (4)Cl4—C161.712 (5)
S5—N51.691 (4)S4—N41.681 (4)
S5—C171.746 (5)S4—C131.750 (5)
O9—C171.398 (5)O7—C131.399 (5)
O9—C181.383 (6)O7—C141.380 (5)
O10—C171.192 (6)O8—C131.189 (5)
N5—C181.274 (6)N4—C141.274 (6)
C18—C191.443 (6)C14—C151.448 (5)
C19—H190.9500C15—H150.9500
C19—C201.328 (6)C15—C161.331 (6)
C20—H200.9500C16—H160.9500
N1—S1—C193.1 (2)N2—S2—C592.9 (2)
C2—O1—C1110.9 (4)C6—O3—C5111.9 (3)
C2—N1—S1110.0 (4)C6—N2—S2109.9 (3)
O1—C1—S1107.2 (3)O3—C5—S2106.9 (3)
O2—C1—S1131.6 (4)O4—C5—S2131.6 (4)
O2—C1—O1121.2 (4)O4—C5—O3121.5 (4)
O1—C2—C3116.4 (5)O3—C6—C7116.2 (4)
N1—C2—O1118.9 (4)N2—C6—O3118.4 (4)
N1—C2—C3124.7 (5)N2—C6—C7125.4 (5)
C2—C3—H3119.2C6—C7—H7119.0
C4—C3—C2121.5 (5)C8—C7—C6122.0 (5)
C4—C3—H3119.2C8—C7—H7119.0
Cl1—C4—H4118.7Cl2—C8—H8118.7
C3—C4—Cl1122.6 (4)C7—C8—Cl2122.6 (4)
C3—C4—H4118.7C7—C8—H8118.7
N6—S6—C2193.3 (2)N3—S3—C993.2 (2)
C22—O11—C21111.6 (4)C10—O5—C9112.0 (4)
C22—N6—S6109.6 (3)C10—N3—S3109.8 (3)
O11—C21—S6106.7 (3)O5—C9—S3106.7 (3)
O12—C21—S6131.9 (4)O6—C9—S3132.1 (4)
O12—C21—O11121.4 (4)O6—C9—O5121.2 (4)
O11—C22—C23116.1 (4)O5—C10—C11116.9 (4)
N6—C22—O11118.8 (4)N3—C10—O5118.2 (4)
N6—C22—C23125.1 (4)N3—C10—C11124.8 (4)
C22—C23—H23119.2C10—C11—H11119.4
C24—C23—C22121.7 (5)C12—C11—C10121.2 (5)
C24—C23—H23119.2C12—C11—H11119.4
Cl6—C24—H24119.2Cl3—C12—H12118.9
C23—C24—Cl6121.5 (4)C11—C12—Cl3122.3 (4)
C23—C24—H24119.2C11—C12—H12118.9
N5—S5—C1793.1 (2)N4—S4—C1393.4 (2)
C18—O9—C17110.9 (4)C14—O7—C13110.9 (4)
C18—N5—S5110.1 (3)C14—N4—S4110.0 (3)
O9—C17—S5107.4 (3)O7—C13—S4106.9 (3)
O10—C17—S5131.9 (4)O8—C13—S4132.1 (3)
O10—C17—O9120.7 (4)O8—C13—O7120.9 (4)
O9—C18—C19116.6 (5)O7—C14—C15116.2 (5)
N5—C18—O9118.5 (4)N4—C14—O7118.7 (4)
N5—C18—C19125.0 (5)N4—C14—C15125.1 (5)
C18—C19—H19119.0C14—C15—H15119.4
C20—C19—C18121.9 (5)C16—C15—C14121.2 (5)
C20—C19—H19119.0C16—C15—H15119.4
Cl5—C20—H20118.6Cl4—C16—H16118.4
C19—C20—Cl5122.8 (4)C15—C16—Cl4123.2 (4)
C19—C20—H20118.6C15—C16—H16118.4
S1—N1—C2—O10.6 (5)S2—N2—C6—O31.6 (5)
S1—N1—C2—C3179.0 (3)S2—N2—C6—C7178.2 (3)
O1—C2—C3—C44.5 (6)O3—C6—C7—C80.8 (6)
N1—S1—C1—O10.3 (3)N2—S2—C5—O30.3 (3)
N1—S1—C1—O2179.9 (4)N2—S2—C5—O4179.9 (4)
N1—C2—C3—C4175.1 (5)N2—C6—C7—C8179.4 (5)
C1—S1—N1—C20.1 (3)C5—S2—N2—C60.7 (3)
C1—O1—C2—N10.9 (6)C5—O3—C6—N21.9 (5)
C1—O1—C2—C3178.8 (3)C5—O3—C6—C7177.9 (3)
C2—O1—C1—S10.7 (4)C6—O3—C5—S21.2 (4)
C2—O1—C1—O2179.5 (4)C6—O3—C5—O4179.0 (4)
C2—C3—C4—Cl1179.4 (3)C6—C7—C8—Cl2179.8 (3)
S6—N6—C22—O110.7 (5)S3—N3—C10—O50.1 (5)
S6—N6—C22—C23179.4 (3)S3—N3—C10—C11178.5 (3)
O11—C22—C23—C241.0 (6)O5—C10—C11—C121.1 (6)
N6—S6—C21—O110.7 (3)N3—S3—C9—O50.5 (3)
N6—S6—C21—O12179.3 (4)N3—S3—C9—O6179.5 (5)
N6—C22—C23—C24178.8 (4)N3—C10—C11—C12179.5 (4)
C21—S6—N6—C220.8 (3)C9—S3—N3—C100.3 (3)
C21—O11—C22—N60.2 (5)C9—O5—C10—N30.3 (5)
C21—O11—C22—C23180.0 (3)C9—O5—C10—C11178.3 (3)
C22—O11—C21—S60.5 (4)C10—O5—C9—S30.5 (4)
C22—O11—C21—O12179.2 (4)C10—O5—C9—O6179.5 (4)
C22—C23—C24—Cl6179.1 (3)C10—C11—C12—Cl3178.9 (3)
S5—N5—C18—O90.3 (5)S4—N4—C14—O71.3 (5)
S5—N5—C18—C19179.7 (3)S4—N4—C14—C15179.3 (3)
O9—C18—C19—C200.2 (6)O7—C14—C15—C160.8 (6)
N5—S5—C17—O90.7 (3)N4—S4—C13—O70.9 (3)
N5—S5—C17—O10179.8 (5)N4—S4—C13—O8178.6 (4)
N5—C18—C19—C20179.2 (4)N4—C14—C15—C16179.8 (5)
C17—S5—N5—C180.2 (4)C13—S4—N4—C140.2 (3)
C17—O9—C18—N50.9 (5)C13—O7—C14—N42.1 (5)
C17—O9—C18—C19179.7 (4)C13—O7—C14—C15178.5 (3)
C18—O9—C17—S50.9 (4)C14—O7—C13—S41.7 (4)
C18—O9—C17—O10179.5 (4)C14—O7—C13—O8177.9 (4)
C18—C19—C20—Cl5178.9 (3)C14—C15—C16—Cl4179.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O7i0.952.823.738 (6)163
C4—H4···N4ii0.952.553.358 (7)143
C23—H23···O5iii0.952.823.739 (6)162
C24—H24···N3iv0.952.523.332 (7)144
C19—H19···O9iv0.952.903.772 (6)153
C20—H20···N5iii0.952.593.398 (7)143
C7—H7···O3ii0.952.833.742 (6)162
C8—H8···N2i0.952.513.306 (7)142
C11—H11···O11iii0.952.913.785 (6)153
C12—H12···N6iv0.952.473.262 (7)141
C15—H15···O1i0.952.853.724 (6)154
C16—H16···N1ii0.952.513.289 (7)140
Symmetry codes: (i) x+1, y+1/2, z; (ii) x+1, y1/2, z; (iii) x+1, y1/2, z+1; (iv) x+1, y+1/2, z+1.
rac-2,3-Dibromo-3-chloropropanamide (2) top
Crystal data top
C3H4Br2ClNOF(000) = 992
Mr = 265.34Dx = 2.409 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 6.5967 (2) ÅCell parameters from 9991 reflections
b = 24.1942 (9) Åθ = 3.2–29.2°
c = 9.1724 (3) ŵ = 11.36 mm1
β = 91.904 (1)°T = 100 K
V = 1463.12 (8) Å3Plate, colourless
Z = 80.28 × 0.16 × 0.09 mm
Data collection top
Bruker D8 Venture
diffractometer
6456 independent reflections
Radiation source: microfocus sealed tube, Incoatec IµS 3.05710 reflections with I > 2σ(I)
Multilayer mirror monochromatorRint = 0.055
Detector resolution: 7.3910 pixels mm-1θmax = 27.1°, θmin = 2.2°
φ and ω scansh = 88
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
k = 3131
Tmin = 0.003, Tmax = 0.020l = 1111
55465 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.048 w = 1/[σ2(Fo2) + (0.0815P)2 + 6.1207P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.139(Δ/σ)max < 0.001
S = 1.08Δρmax = 2.15 e Å3
6456 reflectionsΔρmin = 1.09 e Å3
330 parametersAbsolute structure: Refined as an inversion twin.
20 restraintsAbsolute structure parameter: 0.36 (3)
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
xyzUiso*/UeqOcc. (<1)
Br10.50262 (18)0.42390 (6)0.39370 (15)0.0336 (3)
Br20.0647 (2)0.31951 (6)0.50278 (17)0.0367 (3)
O10.0263 (13)0.4412 (4)0.3090 (8)0.0248 (18)
N10.0006 (16)0.4709 (4)0.5436 (10)0.023 (2)
H1A0.0887350.4963500.5217780.027*
H1B0.0394230.4673790.6339890.027*
C10.0775 (18)0.4376 (5)0.4393 (13)0.023 (2)
Cl10.3898 (11)0.2953 (3)0.5101 (10)0.0318 (14)0.790 (19)
C20.241 (2)0.3975 (6)0.4850 (15)0.022 (3)0.790 (19)
H20.2499770.3976580.5936040.027*0.790 (19)
C30.206 (2)0.3400 (6)0.4326 (15)0.021 (3)0.790 (19)
H30.2163750.3384750.3236960.025*0.790 (19)
Br31.24147 (18)0.42218 (6)0.90633 (16)0.0340 (3)
Br40.6737 (2)0.31877 (7)0.99094 (17)0.0401 (3)
O20.7698 (13)0.4431 (4)0.8074 (9)0.0241 (18)
N20.7492 (15)0.4690 (4)1.0423 (10)0.022 (2)
H2B0.6600040.4949561.0203520.026*
H2C0.7899730.4638321.1336670.026*
C40.8221 (18)0.4376 (5)0.9381 (13)0.023 (2)
Cl21.1256 (10)0.2896 (3)0.9763 (8)0.0261 (12)0.86 (2)
C50.985 (2)0.3953 (6)0.9835 (15)0.024 (3)0.86 (2)
H50.9966870.3926481.0922690.028*0.86 (2)
C60.938 (2)0.3392 (6)0.9189 (16)0.024 (3)0.86 (2)
H60.9304850.3416730.8100090.029*0.86 (2)
Br50.74005 (19)0.57855 (6)0.35901 (17)0.0361 (3)
Br60.1720 (2)0.68113 (7)0.24460 (18)0.0405 (4)
O30.2669 (13)0.5582 (4)0.4397 (9)0.0232 (17)
N30.2421 (16)0.5301 (5)0.2051 (11)0.026 (2)
H3B0.1579890.5031580.2258010.032*
H3C0.2788630.5350090.1146430.032*
C70.314 (2)0.5633 (5)0.3106 (13)0.024 (3)
Cl30.6239 (12)0.7105 (3)0.2630 (12)0.0234 (15)0.789 (19)
C80.482 (2)0.6037 (6)0.2695 (16)0.021 (3)0.789 (19)
H80.4921350.6047630.1610140.025*0.789 (19)
C90.440 (2)0.6607 (7)0.3256 (17)0.024 (3)0.789 (19)
H90.4396600.6605530.4345610.028*0.789 (19)
Br70.00734 (19)0.57685 (6)0.83633 (16)0.0335 (3)
Br80.5604 (2)0.68245 (7)0.77338 (19)0.0435 (4)
O40.4649 (13)0.5577 (4)0.9451 (9)0.0251 (18)
N40.4886 (16)0.5309 (5)0.7086 (10)0.025 (2)
H4A0.5721390.5035900.7310300.030*
H4B0.4509950.5368200.6170120.030*
C100.420 (2)0.5629 (5)0.8122 (14)0.025 (2)
Cl40.1061 (10)0.7086 (3)0.7369 (8)0.0266 (11)0.817 (19)
C110.251 (2)0.6031 (6)0.7628 (15)0.024 (3)0.817 (19)
H110.2423680.6042100.6537550.029*0.817 (19)
C120.287 (2)0.6613 (6)0.8207 (17)0.024 (3)0.817 (19)
H120.2729430.6616020.9289670.029*0.817 (19)
Cl1A0.430 (5)0.3001 (15)0.482 (4)0.0318 (14)0.210 (19)
Cl2A1.166 (7)0.2983 (18)0.987 (6)0.0261 (12)0.14 (2)
Cl3A0.656 (5)0.7030 (15)0.281 (5)0.0234 (15)0.211 (19)
Cl4A0.060 (5)0.6990 (12)0.735 (4)0.0266 (11)0.183 (19)
C2A0.138 (5)0.3804 (11)0.500 (5)0.022 (3)0.210 (19)
H2A0.1848000.3857020.6013680.027*0.210 (19)
C3A0.311 (6)0.3600 (13)0.408 (5)0.021 (3)0.210 (19)
H3A0.2632070.3510380.3086590.025*0.210 (19)
C5A0.874 (6)0.3793 (13)1.001 (7)0.024 (3)0.14 (2)
H5A0.9220760.3836941.1045450.028*0.14 (2)
C6A1.050 (7)0.3599 (17)0.912 (8)0.024 (3)0.14 (2)
H6A0.9996430.3517790.8107650.029*0.14 (2)
C8A0.377 (6)0.6201 (12)0.247 (5)0.021 (3)0.211 (19)
H8A0.4326750.6150720.1474550.025*0.211 (19)
C9A0.550 (6)0.6410 (15)0.358 (6)0.024 (3)0.211 (19)
H9A0.4961030.6478860.4568950.028*0.211 (19)
C11A0.361 (6)0.6217 (12)0.756 (6)0.024 (3)0.183 (19)
H11A0.3227570.6180000.6498140.029*0.183 (19)
C12A0.173 (6)0.6409 (14)0.833 (6)0.024 (3)0.183 (19)
H12A0.2104390.6522500.9348870.029*0.183 (19)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0229 (6)0.0304 (7)0.0475 (8)0.0031 (5)0.0021 (5)0.0092 (6)
Br20.0268 (6)0.0326 (7)0.0505 (8)0.0044 (6)0.0001 (5)0.0080 (6)
O10.031 (4)0.029 (5)0.015 (4)0.003 (4)0.002 (3)0.001 (3)
N10.031 (5)0.024 (5)0.013 (4)0.005 (4)0.001 (4)0.002 (4)
C10.025 (6)0.023 (6)0.020 (5)0.005 (5)0.003 (4)0.006 (4)
Cl10.027 (3)0.020 (2)0.048 (4)0.006 (2)0.002 (2)0.006 (2)
C20.023 (8)0.029 (9)0.016 (6)0.003 (6)0.008 (6)0.004 (6)
C30.021 (7)0.028 (8)0.013 (6)0.002 (6)0.007 (5)0.003 (5)
Br30.0230 (6)0.0305 (7)0.0487 (8)0.0015 (5)0.0031 (5)0.0072 (6)
Br40.0294 (7)0.0365 (8)0.0545 (9)0.0023 (6)0.0013 (6)0.0026 (7)
O20.029 (4)0.024 (5)0.020 (4)0.003 (3)0.002 (3)0.006 (3)
N20.024 (5)0.026 (5)0.015 (4)0.002 (4)0.003 (4)0.007 (4)
C40.025 (5)0.017 (6)0.027 (6)0.003 (5)0.005 (4)0.004 (4)
Cl20.022 (3)0.017 (3)0.040 (2)0.0054 (17)0.000 (2)0.0030 (19)
C50.028 (7)0.025 (7)0.017 (6)0.008 (6)0.003 (5)0.002 (5)
C60.021 (6)0.022 (7)0.030 (7)0.000 (5)0.005 (5)0.004 (6)
Br50.0238 (6)0.0314 (7)0.0533 (8)0.0038 (5)0.0029 (5)0.0106 (7)
Br60.0295 (7)0.0380 (8)0.0538 (9)0.0035 (6)0.0003 (6)0.0093 (7)
O30.028 (4)0.027 (5)0.014 (4)0.007 (4)0.001 (3)0.001 (3)
N30.025 (5)0.034 (6)0.019 (5)0.001 (4)0.003 (4)0.004 (4)
C70.030 (6)0.026 (6)0.016 (5)0.003 (5)0.001 (4)0.000 (4)
Cl30.018 (3)0.008 (3)0.045 (4)0.002 (2)0.010 (3)0.000 (2)
C80.018 (7)0.025 (8)0.020 (6)0.000 (6)0.003 (5)0.001 (5)
C90.022 (7)0.022 (7)0.027 (7)0.002 (6)0.003 (6)0.005 (6)
Br70.0243 (6)0.0284 (7)0.0477 (7)0.0020 (5)0.0020 (5)0.0037 (6)
Br80.0304 (7)0.0382 (8)0.0618 (10)0.0032 (6)0.0002 (6)0.0104 (7)
O40.032 (5)0.029 (5)0.014 (4)0.002 (4)0.002 (3)0.000 (3)
N40.029 (5)0.033 (6)0.014 (4)0.002 (5)0.002 (4)0.001 (4)
C100.029 (6)0.021 (6)0.025 (6)0.002 (5)0.002 (5)0.001 (5)
Cl40.021 (3)0.011 (2)0.0485 (19)0.0031 (18)0.005 (2)0.002 (2)
C110.033 (8)0.024 (8)0.017 (6)0.005 (6)0.004 (6)0.001 (5)
C120.019 (6)0.027 (8)0.028 (7)0.010 (5)0.004 (5)0.001 (6)
Cl1A0.027 (3)0.020 (2)0.048 (4)0.006 (2)0.002 (2)0.006 (2)
Cl2A0.022 (3)0.017 (3)0.040 (2)0.0054 (17)0.000 (2)0.0030 (19)
Cl3A0.018 (3)0.008 (3)0.045 (4)0.002 (2)0.010 (3)0.000 (2)
Cl4A0.021 (3)0.011 (2)0.0485 (19)0.0031 (18)0.005 (2)0.002 (2)
C2A0.023 (8)0.029 (9)0.016 (6)0.003 (6)0.008 (6)0.004 (6)
C3A0.021 (7)0.028 (8)0.013 (6)0.002 (6)0.007 (5)0.003 (5)
C5A0.028 (7)0.025 (7)0.017 (6)0.008 (6)0.003 (5)0.002 (5)
C6A0.021 (6)0.022 (7)0.030 (7)0.000 (5)0.005 (5)0.004 (6)
C8A0.018 (7)0.025 (8)0.020 (6)0.000 (6)0.003 (5)0.001 (5)
C9A0.022 (7)0.022 (7)0.027 (7)0.002 (6)0.003 (6)0.005 (6)
C11A0.033 (8)0.024 (8)0.017 (6)0.005 (6)0.004 (6)0.001 (5)
C12A0.019 (6)0.027 (8)0.028 (7)0.010 (5)0.004 (5)0.001 (6)
Geometric parameters (Å, º) top
Br1—C21.997 (16)C7—C81.533 (19)
Br1—C3A2.00 (3)C7—C8A1.56 (3)
Br2—C31.944 (14)Cl3—C91.813 (16)
Br2—C2A1.99 (3)C8—H81.0000
O1—C11.256 (14)C8—C91.50 (2)
N1—H1A0.8800C9—H91.0000
N1—H1B0.8800Br7—C111.961 (15)
N1—C11.338 (15)Br7—C12A1.95 (3)
C1—C21.519 (18)Br8—C121.939 (14)
C1—C2A1.55 (3)Br8—C11A1.97 (3)
Cl1—C31.789 (15)O4—C101.251 (15)
C2—H21.0000N4—H4A0.8800
C2—C31.49 (2)N4—H4B0.8800
C3—H31.0000N4—C101.317 (16)
Br3—C51.965 (15)C10—C111.54 (2)
Br3—C6A1.97 (3)C10—C11A1.56 (3)
Br4—C61.946 (14)Cl4—C121.806 (16)
Br4—C5A1.97 (3)C11—H111.0000
O2—C41.243 (14)C11—C121.519 (19)
N2—H2B0.8800C12—H121.0000
N2—H2C0.8800Cl1A—C3A1.79 (3)
N2—C41.324 (15)Cl2A—C6A1.80 (3)
C4—C51.533 (17)Cl3A—C9A1.81 (3)
C4—C5A1.56 (3)Cl4A—C12A1.81 (3)
Cl2—C61.793 (15)C2A—H2A1.0000
C5—H51.0000C2A—C3A1.48 (3)
C5—C61.509 (19)C3A—H3A1.0000
C6—H61.0000C5A—H5A1.0000
Br5—C81.964 (15)C5A—C6A1.52 (3)
Br5—C9A1.96 (3)C6A—H6A1.0000
Br6—C91.961 (15)C8A—H8A1.0000
Br6—C8A2.00 (3)C8A—C9A1.59 (7)
O3—C71.240 (15)C9A—H9A1.0000
N3—H3B0.8800C11A—H11A1.0000
N3—H3C0.8800C11A—C12A1.52 (3)
N3—C71.333 (16)C12A—H12A1.0000
H1A—N1—H1B120.0O4—C10—C11119.8 (11)
C1—N1—H1A120.0O4—C10—C11A118 (2)
C1—N1—H1B120.0N4—C10—C11115.0 (11)
O1—C1—N1122.0 (11)N4—C10—C11A113 (2)
O1—C1—C2121.6 (11)Br7—C11—H11109.2
O1—C1—C2A119.0 (19)C10—C11—Br7108.8 (9)
N1—C1—C2116.3 (10)C10—C11—H11109.2
N1—C1—C2A112.2 (19)C12—C11—Br7107.8 (9)
Br1—C2—H2109.8C12—C11—C10112.5 (12)
C1—C2—Br1107.0 (10)C12—C11—H11109.2
C1—C2—H2109.8Br8—C12—H12109.7
C3—C2—Br1107.6 (10)Cl4—C12—Br8110.1 (8)
C3—C2—C1112.8 (11)Cl4—C12—H12109.7
C3—C2—H2109.8C11—C12—Br8107.5 (10)
Br2—C3—H3110.5C11—C12—Cl4110.2 (10)
Cl1—C3—Br2109.9 (8)C11—C12—H12109.7
Cl1—C3—H3110.5Br2—C2A—H2A108.2
C2—C3—Br2106.3 (10)C1—C2A—Br2119 (2)
C2—C3—Cl1108.9 (10)C1—C2A—H2A108.2
C2—C3—H3110.5C3A—C2A—Br2105 (2)
H2B—N2—H2C120.0C3A—C2A—C1107 (3)
C4—N2—H2B120.0C3A—C2A—H2A108.2
C4—N2—H2C120.0Br1—C3A—H3A109.0
O2—C4—N2122.7 (11)Cl1A—C3A—Br1112 (2)
O2—C4—C5120.2 (11)Cl1A—C3A—H3A109.0
O2—C4—C5A120 (3)C2A—C3A—Br1105 (2)
N2—C4—C5117.1 (11)C2A—C3A—Cl1A113 (3)
N2—C4—C5A109 (3)C2A—C3A—H3A109.0
Br3—C5—H5110.0Br4—C5A—H5A108.3
C4—C5—Br3106.6 (9)C4—C5A—Br4121 (2)
C4—C5—H5110.0C4—C5A—H5A108.3
C6—C5—Br3109.1 (9)C6A—C5A—Br4106 (3)
C6—C5—C4111.0 (11)C6A—C5A—C4104 (3)
C6—C5—H5110.0C6A—C5A—H5A108.3
Br4—C6—H6110.0Br3—C6A—H6A108.6
Cl2—C6—Br4110.4 (8)Cl2A—C6A—Br3113 (3)
Cl2—C6—H6110.0Cl2A—C6A—H6A108.6
C5—C6—Br4105.8 (9)C5A—C6A—Br3106 (3)
C5—C6—Cl2110.7 (10)C5A—C6A—Cl2A112 (4)
C5—C6—H6110.0C5A—C6A—H6A108.6
H3B—N3—H3C120.0Br6—C8A—H8A110.3
C7—N3—H3B120.0C7—C8A—Br6118 (2)
C7—N3—H3C120.0C7—C8A—H8A110.3
O3—C7—N3122.7 (12)C7—C8A—C9A104 (3)
O3—C7—C8120.2 (11)C9A—C8A—Br6104 (2)
O3—C7—C8A122 (2)C9A—C8A—H8A110.3
N3—C7—C8116.6 (11)Br5—C9A—H9A111.7
N3—C7—C8A111 (2)Cl3A—C9A—Br5113 (2)
Br5—C8—H8109.6Cl3A—C9A—H9A111.7
C7—C8—Br5108.9 (9)C8A—C9A—Br5102 (2)
C7—C8—H8109.6C8A—C9A—Cl3A107 (3)
C9—C8—Br5107.8 (9)C8A—C9A—H9A111.7
C9—C8—C7111.2 (12)Br8—C11A—H11A107.0
C9—C8—H8109.6C10—C11A—Br8120 (2)
Br6—C9—H9110.2C10—C11A—H11A107.0
Cl3—C9—Br6108.5 (8)C12A—C11A—Br8107 (2)
Cl3—C9—H9110.2C12A—C11A—C10109 (3)
C8—C9—Br6105.8 (10)C12A—C11A—H11A107.0
C8—C9—Cl3111.8 (10)Br7—C12A—H12A109.6
C8—C9—H9110.2Cl4A—C12A—Br7113 (2)
H4A—N4—H4B120.0Cl4A—C12A—H12A109.6
C10—N4—H4A120.0C11A—C12A—Br7106 (2)
C10—N4—H4B120.0C11A—C12A—Cl4A109 (3)
O4—C10—N4124.6 (12)C11A—C12A—H12A109.6
Br1—C2—C3—Br2172.7 (6)Br5—C8—C9—Br6175.7 (7)
Br1—C2—C3—Cl168.9 (10)Br5—C8—C9—Cl366.3 (12)
Br2—C2A—C3A—Br1175.6 (18)Br6—C8A—C9A—Br5178.3 (18)
Br2—C2A—C3A—Cl1A62 (3)Br6—C8A—C9A—Cl3A63 (3)
O1—C1—C2—Br167.0 (14)O3—C7—C8—Br564.4 (15)
O1—C1—C2—C351.2 (17)O3—C7—C8—C954.2 (17)
O1—C1—C2A—Br261 (3)O3—C7—C8A—Br662 (4)
O1—C1—C2A—C3A59 (3)O3—C7—C8A—C9A52 (3)
N1—C1—C2—Br1109.0 (11)N3—C7—C8—Br5107.4 (11)
N1—C1—C2—C3132.8 (12)N3—C7—C8—C9133.9 (13)
N1—C1—C2A—Br291 (3)N3—C7—C8A—Br694 (3)
N1—C1—C2A—C3A149 (2)N3—C7—C8A—C9A152 (2)
C1—C2—C3—Br254.9 (13)C7—C8—C9—Br656.4 (13)
C1—C2—C3—Cl1173.3 (10)C7—C8—C9—Cl3174.4 (10)
C1—C2A—C3A—Br148 (3)C7—C8A—C9A—Br555 (3)
C1—C2A—C3A—Cl1A169 (3)C7—C8A—C9A—Cl3A173 (2)
Br3—C5—C6—Br4176.1 (6)Br7—C11—C12—Br8171.2 (7)
Br3—C5—C6—Cl264.3 (11)Br7—C11—C12—Cl468.8 (11)
Br4—C5A—C6A—Br3175 (3)Br8—C11A—C12A—Br7173 (2)
Br4—C5A—C6A—Cl2A61 (4)Br8—C11A—C12A—Cl4A66 (3)
O2—C4—C5—Br367.9 (13)O4—C10—C11—Br764.9 (14)
O2—C4—C5—C650.7 (16)O4—C10—C11—C1254.4 (17)
O2—C4—C5A—Br458 (5)O4—C10—C11A—Br861 (4)
O2—C4—C5A—C6A61 (4)O4—C10—C11A—C12A62 (3)
N2—C4—C5—Br3109.0 (11)N4—C10—C11—Br7106.6 (11)
N2—C4—C5—C6132.3 (12)N4—C10—C11—C12134.1 (12)
N2—C4—C5A—Br492 (4)N4—C10—C11A—Br894 (3)
N2—C4—C5A—C6A149 (3)N4—C10—C11A—C12A143 (3)
C4—C5—C6—Br459.0 (12)C10—C11—C12—Br851.3 (13)
C4—C5—C6—Cl2178.6 (10)C10—C11—C12—Cl4171.2 (10)
C4—C5A—C6A—Br346 (4)C10—C11A—C12A—Br742 (4)
C4—C5A—C6A—Cl2A170 (3)C10—C11A—C12A—Cl4A164 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O30.882.062.932 (13)170
N1—H1B···O2i0.882.142.974 (13)157
C2—H2···O2i1.002.253.154 (16)150
N2—H2B···O40.882.092.968 (14)173
N2—H2C···O1ii0.882.062.896 (13)159
C5—H5···O1ii1.002.323.189 (16)145
N3—H3B···O10.882.092.962 (14)171
N3—H3C···O4iii0.882.092.920 (13)158
C8—H8···O4iii1.002.293.175 (17)147
N4—H4A···O20.882.072.944 (14)174
N4—H4B···O30.882.062.902 (13)159
C11—H11···O31.002.273.161 (16)148
C2A—H2A···O2i1.002.373.28 (4)150
C5A—H5A···O1ii1.002.353.25 (6)149
C8A—H8A···O4iii1.002.333.22 (5)147
C11A—H11A···O31.002.433.32 (5)148
Symmetry codes: (i) x1, y, z; (ii) x+1, y, z+1; (iii) x, y, z1.
rac-5-(1,2-Dibromo-2-phenylethyl)-1,3,4-oxathiazol-2-one (3) top
Crystal data top
C10H7Br2NO2SDx = 2.118 Mg m3
Mr = 365.05Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca21Cell parameters from 9932 reflections
a = 7.1195 (2) Åθ = 3.1–35.0°
b = 16.4402 (5) ŵ = 7.24 mm1
c = 9.7821 (3) ÅT = 100 K
V = 1144.96 (6) Å3Rect. Prism, colourless
Z = 40.21 × 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 3.04815 reflections with I > 2σ(I)
Multilayer mirror monochromatorRint = 0.036
Detector resolution: 7.3910 pixels mm-1θmax = 35.0°, θmin = 3.1°
φ and ω scansh = 1111
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
k = 2626
Tmin = 0.448, Tmax = 0.747l = 1515
43632 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.016 w = 1/[σ2(Fo2) + (0.0118P)2 + 0.1534P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.036(Δ/σ)max = 0.001
S = 1.02Δρmax = 0.50 e Å3
5019 reflectionsΔρmin = 0.38 e Å3
255 parametersAbsolute structure: Refined as an inversion twin.
220 restraintsAbsolute structure parameter: 0.040 (6)
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
xyzUiso*/UeqOcc. (<1)
S10.5403 (2)0.44452 (14)0.7052 (2)0.0175 (2)0.883 (4)
O10.6961 (4)0.50389 (19)0.4757 (4)0.0188 (4)0.883 (4)
O20.5069 (4)0.39365 (17)0.4616 (3)0.0132 (4)0.883 (4)
N10.4023 (6)0.3619 (2)0.6761 (3)0.0164 (5)0.883 (4)
C10.5980 (9)0.4550 (4)0.5332 (8)0.0138 (6)0.883 (4)
C20.4019 (3)0.34742 (13)0.5477 (3)0.0132 (3)0.883 (4)
C30.2979 (3)0.28028 (11)0.4789 (2)0.0132 (4)0.883 (4)
H30.2440250.3004270.3907740.016*0.883 (4)
C40.1438 (3)0.24127 (11)0.5639 (2)0.0135 (4)0.883 (4)
H40.1996080.2224920.6522720.016*0.883 (4)
C50.0473 (4)0.17027 (15)0.4973 (3)0.0142 (4)0.883 (4)
C60.0196 (5)0.17478 (18)0.3631 (3)0.0178 (4)0.883 (4)
H60.0010180.2228970.3110820.021*0.883 (4)
C70.1133 (7)0.1089 (2)0.3058 (3)0.0185 (5)0.883 (4)
H70.1573680.1119680.2143160.022*0.883 (4)
C80.1428 (6)0.0386 (2)0.3819 (4)0.0190 (7)0.883 (4)
H80.2090450.0058800.3430640.023*0.883 (4)
C90.0755 (4)0.03364 (15)0.5142 (3)0.0189 (4)0.883 (4)
H90.0947430.0145370.5659510.023*0.883 (4)
C100.0207 (4)0.09914 (16)0.5720 (3)0.0154 (4)0.883 (4)
H100.0681500.0951540.6625060.019*0.883 (4)
Br10.48888 (7)0.19548 (4)0.44095 (6)0.01456 (9)0.883 (4)
Br20.04519 (14)0.32648 (7)0.60411 (7)0.01761 (10)0.883 (4)
Br2A0.0407 (14)0.3295 (6)0.5833 (17)0.042 (3)0.117 (4)
S1A0.564 (2)0.4441 (12)0.715 (2)0.0175 (2)0.117 (4)
N1A0.418 (6)0.368 (2)0.708 (3)0.024 (5)0.117 (4)
C1A0.581 (8)0.447 (4)0.525 (7)0.0138 (6)0.117 (4)
C2A0.416 (2)0.3401 (10)0.595 (2)0.0132 (3)0.117 (4)
O1A0.658 (4)0.4908 (17)0.460 (3)0.026 (4)0.117 (4)
O2A0.483 (4)0.3799 (17)0.485 (2)0.020 (4)0.117 (4)
C3A0.317 (2)0.2561 (11)0.5610 (16)0.023 (3)0.117 (4)
H3A0.2929630.2260900.6481240.027*0.117 (4)
C4A0.142 (2)0.2646 (10)0.4859 (17)0.020 (3)0.117 (4)
H4A0.1708130.2927440.3976230.024*0.117 (4)
Br1A0.4910 (10)0.1916 (4)0.4461 (16)0.050 (2)0.117 (4)
C6A0.035 (4)0.1687 (13)0.3235 (17)0.029 (5)0.117 (4)
H6A0.0270580.2090790.2542590.034*0.117 (4)
C5A0.041 (3)0.1836 (9)0.4521 (18)0.018 (3)0.117 (4)
C10A0.030 (3)0.1246 (10)0.5534 (15)0.018 (3)0.117 (4)
H10A0.0820350.1347490.6412440.021*0.117 (4)
C9A0.057 (3)0.0506 (9)0.526 (2)0.0189 (4)0.117 (4)
H9A0.0640450.0101880.5954810.023*0.117 (4)
C8A0.132 (5)0.0356 (13)0.398 (3)0.029 (7)0.117 (4)
H8A0.1916330.0149290.3791080.035*0.117 (4)
C7A0.121 (5)0.0947 (16)0.296 (2)0.027 (6)0.117 (4)
H7A0.1731410.0845160.2084950.033*0.117 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0180 (6)0.0199 (2)0.0146 (4)0.0042 (4)0.0026 (3)0.0035 (3)
O10.0169 (11)0.0158 (11)0.0237 (9)0.0061 (7)0.0031 (9)0.0016 (8)
O20.0145 (9)0.0116 (9)0.0134 (11)0.0027 (6)0.0007 (7)0.0008 (7)
N10.0198 (10)0.0133 (12)0.0161 (13)0.0035 (8)0.0005 (11)0.0013 (10)
C10.0137 (16)0.0109 (17)0.0169 (14)0.0006 (10)0.0020 (11)0.0043 (11)
C20.0138 (7)0.0115 (7)0.0144 (9)0.0011 (6)0.0023 (7)0.0009 (7)
C30.0137 (7)0.0114 (7)0.0146 (8)0.0002 (6)0.0013 (6)0.0011 (6)
C40.0134 (7)0.0112 (7)0.0158 (9)0.0002 (5)0.0011 (6)0.0002 (6)
C50.0140 (8)0.0122 (9)0.0166 (10)0.0026 (7)0.0016 (9)0.0005 (8)
C60.0182 (10)0.0162 (10)0.0191 (11)0.0053 (7)0.0048 (10)0.0004 (9)
C70.0153 (13)0.0207 (13)0.0194 (11)0.0043 (9)0.0025 (9)0.0041 (9)
C80.0145 (15)0.0182 (16)0.0243 (12)0.0043 (11)0.0033 (10)0.0076 (11)
C90.0196 (10)0.0115 (10)0.0255 (10)0.0035 (8)0.0054 (8)0.0033 (9)
C100.0180 (9)0.0113 (10)0.0170 (9)0.0011 (8)0.0017 (7)0.0004 (8)
Br10.01267 (17)0.01285 (18)0.01815 (15)0.00092 (14)0.00122 (13)0.00465 (15)
Br20.01344 (17)0.01324 (18)0.02615 (19)0.00243 (12)0.00060 (14)0.00444 (12)
Br2A0.026 (2)0.024 (2)0.077 (7)0.0024 (14)0.013 (3)0.008 (3)
S1A0.0180 (6)0.0199 (2)0.0146 (4)0.0042 (4)0.0026 (3)0.0035 (3)
N1A0.031 (12)0.020 (9)0.019 (8)0.014 (8)0.007 (8)0.009 (7)
C1A0.0137 (16)0.0109 (17)0.0169 (14)0.0006 (10)0.0020 (11)0.0043 (11)
C2A0.0138 (7)0.0115 (7)0.0144 (9)0.0011 (6)0.0023 (7)0.0009 (7)
O1A0.025 (10)0.020 (8)0.034 (10)0.013 (5)0.003 (7)0.002 (6)
O2A0.024 (8)0.023 (8)0.012 (7)0.009 (5)0.001 (5)0.005 (5)
C3A0.024 (6)0.030 (7)0.014 (6)0.010 (5)0.003 (5)0.003 (6)
C4A0.028 (7)0.019 (6)0.013 (6)0.002 (5)0.004 (5)0.002 (5)
Br1A0.034 (3)0.020 (2)0.096 (5)0.0028 (18)0.004 (3)0.004 (3)
C6A0.025 (10)0.036 (10)0.024 (9)0.000 (7)0.010 (9)0.005 (8)
C5A0.018 (7)0.014 (6)0.022 (8)0.001 (4)0.000 (8)0.001 (6)
C10A0.016 (7)0.015 (7)0.021 (8)0.002 (6)0.002 (6)0.005 (6)
C9A0.0196 (10)0.0115 (10)0.0255 (10)0.0035 (8)0.0054 (8)0.0033 (9)
C8A0.024 (16)0.017 (12)0.046 (10)0.001 (10)0.004 (9)0.015 (9)
C7A0.015 (10)0.029 (11)0.038 (10)0.005 (8)0.006 (8)0.021 (7)
Geometric parameters (Å, º) top
S1—N11.701 (4)Br2A—C4A1.93 (2)
S1—C11.741 (9)S1A—N1A1.62 (4)
O1—C11.204 (7)S1A—C1A1.86 (7)
O2—C11.388 (5)N1A—C2A1.20 (3)
O2—C21.358 (3)C1A—O1A1.10 (6)
N1—C21.278 (3)C1A—O2A1.36 (5)
C2—C31.490 (3)C2A—O2A1.35 (3)
C3—H31.0000C2A—C3A1.58 (2)
C3—C41.519 (3)C3A—H3A1.0000
C3—Br11.9822 (19)C3A—C4A1.45 (2)
C4—H41.0000C3A—Br1A1.98 (2)
C4—C51.503 (3)C4A—H4A1.0000
C4—Br21.982 (2)C4A—C5A1.55 (2)
C5—C61.398 (3)C6A—H6A0.9500
C5—C101.392 (3)C6A—C5A1.3900
C6—H60.9500C6A—C7A1.3900
C6—C71.389 (4)C5A—C10A1.3900
C7—H70.9500C10A—H10A0.9500
C7—C81.391 (4)C10A—C9A1.3900
C8—H80.9500C9A—H9A0.9500
C8—C91.382 (4)C9A—C8A1.3900
C9—H90.9500C8A—H8A0.9500
C9—C101.396 (3)C8A—C7A1.3900
C10—H100.9500C7A—H7A0.9500
N1—S1—C193.06 (19)N1A—S1A—C1A91.1 (19)
C2—O2—C1110.6 (4)C2A—N1A—S1A110 (3)
C2—N1—S1108.3 (3)O1A—C1A—S1A128 (4)
O1—C1—S1130.8 (4)O1A—C1A—O2A128 (6)
O1—C1—O2121.4 (6)O2A—C1A—S1A103 (4)
O2—C1—S1107.8 (4)N1A—C2A—O2A123 (2)
O2—C2—C3114.1 (2)N1A—C2A—C3A123 (2)
N1—C2—O2120.3 (3)O2A—C2A—C3A114.4 (18)
N1—C2—C3125.6 (3)C2A—O2A—C1A110 (4)
C2—C3—H3109.6C2A—C3A—H3A109.2
C2—C3—C4115.11 (16)C2A—C3A—Br1A108.1 (11)
C2—C3—Br1105.36 (13)C4A—C3A—C2A113.6 (15)
C4—C3—H3109.6C4A—C3A—H3A109.2
C4—C3—Br1107.52 (12)C4A—C3A—Br1A107.4 (11)
Br1—C3—H3109.6Br1A—C3A—H3A109.2
C3—C4—H4108.5Br2A—C4A—H4A107.9
C3—C4—Br2107.50 (13)C3A—C4A—Br2A112.4 (12)
C5—C4—C3114.87 (17)C3A—C4A—H4A107.9
C5—C4—H4108.5C3A—C4A—C5A115.1 (15)
C5—C4—Br2108.95 (15)C5A—C4A—Br2A105.4 (12)
Br2—C4—H4108.5C5A—C4A—H4A107.9
C6—C5—C4121.4 (2)C5A—C6A—H6A120.0
C10—C5—C4119.2 (2)C5A—C6A—C7A120.0
C10—C5—C6119.4 (2)C7A—C6A—H6A120.0
C5—C6—H6120.0C6A—C5A—C4A121.7 (13)
C7—C6—C5120.1 (2)C10A—C5A—C4A118.3 (13)
C7—C6—H6120.0C10A—C5A—C6A120.0
C6—C7—H7119.9C5A—C10A—H10A120.0
C6—C7—C8120.3 (3)C5A—C10A—C9A120.0
C8—C7—H7119.9C9A—C10A—H10A120.0
C7—C8—H8120.1C10A—C9A—H9A120.0
C9—C8—C7119.9 (2)C8A—C9A—C10A120.0
C9—C8—H8120.1C8A—C9A—H9A120.0
C8—C9—H9119.9C9A—C8A—H8A120.0
C8—C9—C10120.2 (2)C9A—C8A—C7A120.0
C10—C9—H9119.9C7A—C8A—H8A120.0
C5—C10—C9120.2 (2)C6A—C7A—H7A120.0
C5—C10—H10119.9C8A—C7A—C6A120.0
C9—C10—H10119.9C8A—C7A—H7A120.0
S1—N1—C2—O22.2 (4)Br2A—C4A—C5A—C6A100.0 (16)
S1—N1—C2—C3179.85 (19)Br2A—C4A—C5A—C10A81.2 (15)
O2—C2—C3—C4165.4 (2)S1A—N1A—C2A—O2A17 (4)
O2—C2—C3—Br176.3 (2)S1A—N1A—C2A—C3A168.4 (18)
N1—S1—C1—O1179.7 (7)S1A—C1A—O2A—C2A0 (5)
N1—S1—C1—O20.0 (5)N1A—S1A—C1A—O1A176 (7)
N1—C2—C3—C416.5 (4)N1A—S1A—C1A—O2A7 (4)
N1—C2—C3—Br1101.7 (3)N1A—C2A—O2A—C1A11 (5)
C1—S1—N1—C21.2 (4)N1A—C2A—C3A—C4A107 (3)
C1—O2—C2—N12.2 (5)N1A—C2A—C3A—Br1A134 (3)
C1—O2—C2—C3179.6 (4)C1A—S1A—N1A—C2A13 (4)
C2—O2—C1—S11.1 (6)C2A—C3A—C4A—Br2A58.7 (17)
C2—O2—C1—O1178.7 (6)C2A—C3A—C4A—C5A179.4 (14)
C2—C3—C4—C5176.43 (18)O1A—C1A—O2A—C2A177 (6)
C2—C3—C4—Br262.15 (19)O2A—C2A—C3A—C4A68 (2)
C3—C4—C5—C648.8 (3)O2A—C2A—C3A—Br1A51 (2)
C3—C4—C5—C10132.5 (2)C3A—C2A—O2A—C1A174 (3)
C4—C5—C6—C7178.0 (3)C3A—C4A—C5A—C6A135.6 (16)
C4—C5—C10—C9177.3 (2)C3A—C4A—C5A—C10A43.3 (19)
C5—C6—C7—C80.7 (4)C4A—C5A—C10A—C9A178.9 (19)
C6—C5—C10—C91.4 (3)Br1A—C3A—C4A—Br2A178.3 (9)
C6—C7—C8—C91.2 (4)Br1A—C3A—C4A—C5A61.0 (16)
C7—C8—C9—C100.5 (4)C6A—C5A—C10A—C9A0.0
C8—C9—C10—C50.8 (3)C5A—C6A—C7A—C8A0.0
C10—C5—C6—C70.6 (4)C5A—C10A—C9A—C8A0.0
Br1—C3—C4—C559.39 (19)C10A—C9A—C8A—C7A0.0
Br1—C3—C4—Br2179.19 (9)C9A—C8A—C7A—C6A0.0
Br2—C4—C5—C671.8 (3)C7A—C6A—C5A—C4A178.9 (19)
Br2—C4—C5—C10106.8 (2)C7A—C6A—C5A—C10A0.0
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···N1i1.002.553.550 (4)175
C6—H6···N1i0.952.733.675 (5)173
C4A—H4A···N1Ai1.002.323.24 (4)152
C6A—H6A···N1Ai0.952.773.57 (5)143
Symmetry code: (i) x+1/2, y, z1/2.
Bond lengths (Å) in known 1,3,4-oxathiazol-2-one structures top
CSD refcodeFragmentNC—C (Å)C—C HybridizationOC—O (Å)NC—O (Å)CN (Å)N—S (Å)S—C (Å)CO (Å)
CEDGUO11.49 (4)sp2sp31.384 (3)1.366 (3)1.262 (3)1.690 (2)1.752 (3)1.188 (3)
GEHZEB11.443 (2)sp2sp21.385 (2)1.368 (2)1.276 (2)1.676 (1)1.738 (2)1.186 (2)
HEMYON11.491 (5)sp2sp31.392 (5)1.377 (5)1.272 (5)1.697 (3)1.750 (4)1.188 (6)
JELVUU11.447 (3)sp2sp21.385 (3)1.361 (2)1.278 (3)1.679 (2)1.746 (2)1.187 (3)
JELVUU21.449 (3)sp2sp21.391 (2)1.364 (2)1.271 (3)1.684 (2)1.761 (2)1.186 (2)
JELWAB11.451 (2)sp2sp21.385 (2)1.375 (1)1.277 (2)1.682 (1)1.746 (1)1.192 (2)
OPIROV11.440 (5)sp2sp21.416 (5)1.383 (4)1.292 (5)1.734 (4)1.713 (4)1.215 (5)
OPIRUB11.434 (6)sp2sp21.421 (9)1.465 (7)1.286 (7)1.736 (6)1.802 (7)1.119 (7)
OPISAI11.461 (5)sp2sp21.400 (5)1.422 (4)1.237 (4)1.711 (2)1.733 (4)1.177 (5)
OPISEM11.41 (1)sp2sp21.376 (8)1.373 (8)1.280 (8)1.705 (7)1.736 (5)1.233 (7)
TUHVAT11.436 (8)sp2sp21.349 (8)1.436 (8)1.272 (9)1.656 (5)1.718 (7)1.214 (8)
ZARBOJ11.500 (4)sp2sp31.391 (3)1.379 (2)1.276 (3)1.694 (2)1.756 (3)1.184 (3)
ZARBOJ21.499 (4)sp2sp31.380(*)1.377 (3)1.269 (3)1.697 (3)1.762 (3)1.186 (4)
ZARBUP11.499 (3)sp2sp31.396 (3)1.375 (3)1.274 (3)1.692 (2)1.754 (2)1.174 (3)
ZIZFET11.457 (6)sp2sp21.380 (6)1.379 (6)1.268 (6)1.683 (4)1.754 (5)1.188 (7)
ZIZFET21.463 (7)sp2sp21.388 (6)1.380 (6)1.266 (5)1.677 (4)1.751 (5)1.184 (6)
(1)1 (of 6)1.445 (6)sp2sp21.398 (5)1.379 (6)1.276 (6)1.688 (4)1.757 (5)1.187 (5)
(3)11.490 (3)sp2sp31.388 (5)1.358 (3)1.278 (3)1.701 (4)1.741 (9)1.204 (7)
 

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