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
CCDC references: 2246703; 2246702; 2246701
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 |
Mr = 163.58 | Dx = 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 | Rint = 0.032 |
Detector resolution: 7.3910 pixels mm-1 | θmax = 29.2°, θmin = 1.1° |
φ and ω scans | h = −12→13 |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | k = −13→13 |
Tmin = 0.703, Tmax = 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(Fo2) + (0.0356P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.085 | (Δ/σ)max = 0.001 |
S = 1.05 | Δρmax = 0.36 e Å−3 |
9072 reflections | Δρmin = −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 | Uiso*/Ueq | |
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···N3iv | 0.95 | 2.52 | 3.332 (7) | 144 |
C19—H19···O9iv | 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···N6iv | 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 |
Mr = 265.34 | Dx = 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 | Rint = 0.055 |
Detector resolution: 7.3910 pixels mm-1 | θmax = 27.1°, θmin = 2.2° |
φ and ω scans | h = −8→8 |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | k = −31→31 |
Tmin = 0.003, Tmax = 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(Fo2) + (0.0815P)2 + 6.1207P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.139 | (Δ/σ)max < 0.001 |
S = 1.08 | Δρmax = 2.15 e Å−3 |
6456 reflections | Δρmin = −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
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 | Uiso*/Ueq | 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 | Dx = 2.118 Mg m−3 |
Mr = 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 | Rint = 0.036 |
Detector resolution: 7.3910 pixels mm-1 | θmax = 35.0°, θmin = 3.1° |
φ and ω scans | h = −11→11 |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | k = −26→26 |
Tmin = 0.448, Tmax = 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(Fo2) + (0.0118P)2 + 0.1534P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.036 | (Δ/σ)max = 0.001 |
S = 1.02 | Δρmax = 0.50 e Å−3 |
5019 reflections | Δρmin = −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
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 | Uiso*/Ueq | 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 topCSD 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) |