


Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536811032533/pv2443sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536811032533/pv2443Isup2.hkl |
![]() | Chemical Markup Language (CML) file https://doi.org/10.1107/S1600536811032533/pv2443Isup3.cml |
CCDC reference: 845406
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean
(C-C) = 0.004 Å
- Disorder in main residue
- R factor = 0.038
- wR factor = 0.085
- Data-to-parameter ratio = 15.9
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT934_ALERT_3_B Number of (Iobs-Icalc)/SigmaW .gt. 10 Outliers . 1
Alert level C DENSD01_ALERT_1_C The ratio of the submitted crystal density and that calculated from the formula is outside the range 0.99 <> 1.01 Crystal density given = 1.679 Calculated crystal density = 1.619 PLAT044_ALERT_1_C Calculated and Reported Dx Differ .............. ? PLAT046_ALERT_1_C Reported Z, MW and D(calc) are Inconsistent .... 1.619 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.6 Ratio PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 2 PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 93
Alert level G PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF .... ? PLAT301_ALERT_3_G Note: Main Residue Disorder ................... 25 Perc. PLAT432_ALERT_2_G Short Inter X...Y Contact Br2 .. C12 .. 3.07 Ang. PLAT432_ALERT_2_G Short Inter X...Y Contact Br2 .. C23 .. 3.35 Ang. PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... # 13 C15 -N1 -C21 1.555 1.555 1.555 12.10 Deg. PLAT811_ALERT_5_G No ADDSYM Analysis: Too Many Excluded Atoms .... !
0 ALERT level A = Most likely a serious problem - resolve or explain 1 ALERT level B = A potentially serious problem, consider carefully 6 ALERT level C = Check. Ensure it is not caused by an omission or oversight 6 ALERT level G = General information/check it is not something unexpected 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 2 ALERT type 5 Informative message, check
A mixture of 2-bromoaniline (300 mg, 1.7 mmol) and triethylamine (529 mg, 5.2 mmol) was prepared in dichloromethane (20ml). Toluene sulfonylchloride (650 mg, 3.4 mmol) was added to the mixture and stirred for about two hours. The mixture was poured on ice and pH was adjusted about 2-3. The precipitate obtained was filtered, washed and dried. Suitable crystals were produced in methanol by slow evaporation.
The H-atoms were positioned at idealized geometry with C—H = 0.95 and 0.98 Å for aryl and methyl groups, respectively, and were refined using a riding model with Uiso(H) = 1.2 Ueq(C) for aromatic & Uiso(H) = 1.5 Ueq(C) for methyl groups. The bromobenzene ring was disordered over two positions with occupancy ratio 0.74: 0.26. The occupancy factors were established in earlier stages of refinement and were fixed in the final refinement cycles. The benzene ring of the smaller fraction of the bromobenzene fragment was constrained as a regular hexagon
Data collection: APEX2 (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009) and X-SEED (Barbour, 2001); software used to prepare material for publication: WinGX (Farrugia, 1999).
C20H18BrNO4S2 | F(000) = 976 |
Mr = 480.38 | Dx = 1.679 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 9904 reflections |
a = 10.5819 (15) Å | θ = 2.3–28.1° |
b = 13.1465 (19) Å | µ = 2.32 mm−1 |
c = 14.235 (2) Å | T = 100 K |
β = 95.478 (2)° | Blocks, colorless |
V = 1971.2 (5) Å3 | 0.38 × 0.33 × 0.24 mm |
Z = 4 |
Bruker KAPPA APEXII CCD diffractometer | 4792 independent reflections |
Radiation source: fine-focus sealed tube | 4320 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
ϕ and ω scans | θmax = 28.3°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −14→13 |
Tmin = 0.472, Tmax = 0.605 | k = −17→17 |
23193 measured reflections | l = −18→18 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.085 | H-atom parameters constrained |
S = 1.24 | w = 1/[σ2(Fo2) + (0.0125P)2 + 3.1006P] where P = (Fo2 + 2Fc2)/3 |
4792 reflections | (Δ/σ)max = 0.001 |
301 parameters | Δρmax = 0.52 e Å−3 |
0 restraints | Δρmin = −0.53 e Å−3 |
C20H18BrNO4S2 | V = 1971.2 (5) Å3 |
Mr = 480.38 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.5819 (15) Å | µ = 2.32 mm−1 |
b = 13.1465 (19) Å | T = 100 K |
c = 14.235 (2) Å | 0.38 × 0.33 × 0.24 mm |
β = 95.478 (2)° |
Bruker KAPPA APEXII CCD diffractometer | 4792 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | 4320 reflections with I > 2σ(I) |
Tmin = 0.472, Tmax = 0.605 | Rint = 0.031 |
23193 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.085 | H-atom parameters constrained |
S = 1.24 | Δρmax = 0.52 e Å−3 |
4792 reflections | Δρmin = −0.53 e Å−3 |
301 parameters |
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. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Br1 | 0.25875 (4) | 0.31399 (3) | 0.20992 (2) | 0.02691 (9) | 0.74 |
Br2 | −0.06672 (10) | 0.62953 (9) | 0.15927 (9) | 0.0346 (3) | 0.26 |
S1 | 0.30298 (5) | 0.58728 (4) | 0.18802 (4) | 0.01811 (12) | |
S2 | 0.19193 (5) | 0.55064 (5) | 0.36828 (4) | 0.01938 (12) | |
O2 | 0.06261 (16) | 0.55206 (14) | 0.38987 (12) | 0.0240 (4) | |
O3 | 0.42299 (16) | 0.56000 (13) | 0.23665 (13) | 0.0239 (4) | |
O4 | 0.27382 (16) | 0.63481 (13) | 0.39241 (12) | 0.0236 (4) | |
O7 | 0.26821 (17) | 0.55219 (13) | 0.09413 (12) | 0.0237 (4) | |
N1 | 0.18608 (18) | 0.54032 (15) | 0.24974 (13) | 0.0180 (4) | |
C1 | 0.2899 (2) | 0.72024 (17) | 0.19019 (17) | 0.0185 (4) | |
C2 | 0.1987 (2) | 0.76797 (19) | 0.12845 (17) | 0.0214 (5) | |
H2 | 0.1401 | 0.7290 | 0.0885 | 0.026* | |
C3 | 0.1949 (2) | 0.87387 (19) | 0.12623 (18) | 0.0225 (5) | |
H3 | 0.1324 | 0.9074 | 0.0850 | 0.027* | |
C4 | 0.2817 (2) | 0.93112 (18) | 0.18389 (17) | 0.0206 (5) | |
C5 | 0.3712 (2) | 0.88108 (18) | 0.24575 (18) | 0.0219 (5) | |
H5 | 0.4299 | 0.9197 | 0.2858 | 0.026* | |
C6 | 0.3756 (2) | 0.77596 (19) | 0.24962 (17) | 0.0216 (5) | |
H6 | 0.4363 | 0.7424 | 0.2923 | 0.026* | |
C7 | 0.2787 (2) | 1.04533 (19) | 0.1779 (2) | 0.0261 (5) | |
H7A | 0.3330 | 1.0680 | 0.1298 | 0.039* | |
H7B | 0.3100 | 1.0743 | 0.2392 | 0.039* | |
H7C | 0.1914 | 1.0681 | 0.1607 | 0.039* | |
C8 | 0.2633 (2) | 0.43825 (19) | 0.41368 (17) | 0.0220 (5) | |
C9 | 0.3953 (2) | 0.4307 (2) | 0.42161 (17) | 0.0236 (5) | |
H9 | 0.4458 | 0.4872 | 0.4069 | 0.028* | |
C10 | 0.4515 (2) | 0.3396 (2) | 0.45122 (18) | 0.0264 (5) | |
H10 | 0.5415 | 0.3342 | 0.4573 | 0.032* | |
C11 | 0.3788 (3) | 0.2558 (2) | 0.47224 (19) | 0.0291 (6) | |
C12 | 0.2467 (3) | 0.2666 (2) | 0.4662 (2) | 0.0335 (6) | |
H12 | 0.1960 | 0.2107 | 0.4823 | 0.040* | |
C13 | 0.1884 (3) | 0.3570 (2) | 0.4371 (2) | 0.0295 (6) | |
H13 | 0.0986 | 0.3634 | 0.4333 | 0.035* | |
C14 | 0.4414 (3) | 0.1552 (2) | 0.4977 (2) | 0.0378 (7) | |
H14A | 0.3871 | 0.1155 | 0.5361 | 0.057* | |
H14B | 0.5238 | 0.1670 | 0.5335 | 0.057* | |
H14C | 0.4538 | 0.1175 | 0.4399 | 0.057* | |
C15 | 0.0847 (5) | 0.4829 (4) | 0.2018 (3) | 0.0202 (11) | 0.74 |
C16 | 0.1015 (5) | 0.3805 (4) | 0.1793 (4) | 0.0237 (10) | 0.74 |
C17 | 0.0016 (5) | 0.3249 (3) | 0.1337 (3) | 0.0275 (9) | 0.74 |
H17 | 0.0112 | 0.2545 | 0.1213 | 0.033* | 0.74 |
C18 | −0.1120 (5) | 0.3739 (5) | 0.1067 (3) | 0.0291 (10) | 0.74 |
H18 | −0.1805 | 0.3365 | 0.0755 | 0.035* | 0.74 |
C19 | −0.1272 (4) | 0.4763 (4) | 0.1243 (3) | 0.0275 (9) | 0.74 |
H19 | −0.2045 | 0.5095 | 0.1033 | 0.033* | 0.74 |
C20 | −0.0293 (5) | 0.5305 (4) | 0.1728 (3) | 0.0213 (9) | 0.74 |
H20 | −0.0404 | 0.6005 | 0.1862 | 0.026* | 0.74 |
C21 | 0.1025 (10) | 0.4648 (7) | 0.1985 (9) | 0.012 (4)* | 0.26 |
C22 | 0.1370 (9) | 0.3627 (8) | 0.1979 (8) | 0.025 (4) | 0.26 |
H22 | 0.2186 | 0.3422 | 0.2249 | 0.030* | 0.26 |
C23 | 0.0520 (12) | 0.2907 (6) | 0.1578 (7) | 0.038 (3) | 0.26 |
H23 | 0.0756 | 0.2210 | 0.1574 | 0.046* | 0.26 |
C24 | −0.0673 (11) | 0.3207 (8) | 0.1183 (6) | 0.043 (4) | 0.26 |
H24 | −0.1254 | 0.2715 | 0.0909 | 0.052* | 0.26 |
C25 | −0.1018 (8) | 0.4227 (9) | 0.1189 (7) | 0.028 (3) | 0.26 |
H25 | −0.1834 | 0.4432 | 0.0919 | 0.034* | 0.26 |
C26 | −0.0169 (10) | 0.4947 (6) | 0.1590 (8) | 0.024 (3) | 0.26 |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.03615 (19) | 0.01695 (15) | 0.02757 (18) | 0.00531 (14) | 0.00269 (14) | −0.00062 (13) |
Br2 | 0.0257 (5) | 0.0338 (6) | 0.0445 (6) | 0.0085 (4) | 0.0044 (4) | 0.0156 (5) |
S1 | 0.0176 (3) | 0.0155 (3) | 0.0215 (3) | 0.0006 (2) | 0.0035 (2) | 0.0015 (2) |
S2 | 0.0177 (3) | 0.0218 (3) | 0.0185 (3) | −0.0002 (2) | 0.0010 (2) | 0.0017 (2) |
O2 | 0.0198 (8) | 0.0302 (9) | 0.0221 (9) | 0.0010 (7) | 0.0028 (7) | 0.0013 (7) |
O3 | 0.0193 (8) | 0.0196 (8) | 0.0327 (10) | 0.0025 (7) | 0.0020 (7) | 0.0044 (7) |
O4 | 0.0249 (9) | 0.0241 (9) | 0.0215 (9) | −0.0024 (7) | 0.0003 (7) | −0.0010 (7) |
O7 | 0.0282 (9) | 0.0207 (8) | 0.0232 (9) | −0.0016 (7) | 0.0069 (7) | −0.0007 (7) |
N1 | 0.0181 (9) | 0.0184 (9) | 0.0175 (9) | −0.0026 (8) | 0.0016 (7) | −0.0001 (7) |
C1 | 0.0197 (11) | 0.0141 (10) | 0.0220 (11) | 0.0007 (8) | 0.0037 (9) | 0.0023 (9) |
C2 | 0.0208 (11) | 0.0214 (12) | 0.0216 (12) | −0.0004 (9) | −0.0008 (9) | 0.0015 (9) |
C3 | 0.0208 (11) | 0.0221 (12) | 0.0247 (12) | 0.0034 (9) | 0.0026 (9) | 0.0065 (9) |
C4 | 0.0199 (11) | 0.0166 (11) | 0.0267 (12) | 0.0008 (9) | 0.0094 (9) | 0.0033 (9) |
C5 | 0.0201 (11) | 0.0199 (11) | 0.0256 (12) | −0.0042 (9) | 0.0022 (9) | 0.0005 (9) |
C6 | 0.0199 (11) | 0.0213 (12) | 0.0233 (12) | 0.0000 (9) | −0.0001 (9) | 0.0046 (9) |
C7 | 0.0249 (12) | 0.0175 (11) | 0.0367 (14) | 0.0030 (9) | 0.0072 (11) | 0.0042 (10) |
C8 | 0.0204 (11) | 0.0246 (12) | 0.0207 (11) | 0.0016 (9) | 0.0002 (9) | 0.0067 (9) |
C9 | 0.0211 (12) | 0.0281 (13) | 0.0212 (12) | −0.0026 (10) | −0.0007 (9) | 0.0044 (10) |
C10 | 0.0217 (12) | 0.0341 (14) | 0.0231 (12) | 0.0026 (10) | 0.0009 (10) | 0.0049 (10) |
C11 | 0.0308 (14) | 0.0323 (14) | 0.0249 (13) | 0.0049 (11) | 0.0058 (11) | 0.0100 (11) |
C12 | 0.0281 (14) | 0.0325 (15) | 0.0412 (16) | 0.0007 (11) | 0.0094 (12) | 0.0171 (12) |
C13 | 0.0215 (12) | 0.0332 (14) | 0.0340 (14) | −0.0008 (11) | 0.0047 (11) | 0.0121 (12) |
C14 | 0.0371 (16) | 0.0335 (15) | 0.0436 (17) | 0.0088 (13) | 0.0087 (13) | 0.0165 (13) |
C15 | 0.024 (2) | 0.0188 (18) | 0.019 (2) | −0.0033 (19) | 0.0044 (16) | −0.0018 (15) |
C16 | 0.029 (2) | 0.023 (2) | 0.020 (2) | −0.0013 (18) | 0.0029 (18) | 0.0049 (17) |
C17 | 0.040 (3) | 0.018 (2) | 0.025 (2) | −0.011 (2) | 0.006 (2) | −0.0035 (16) |
C18 | 0.032 (3) | 0.033 (3) | 0.022 (2) | −0.017 (2) | 0.0014 (17) | −0.004 (2) |
C19 | 0.024 (2) | 0.035 (2) | 0.0238 (19) | −0.0046 (18) | 0.0000 (14) | 0.0022 (19) |
C20 | 0.0201 (19) | 0.026 (3) | 0.018 (2) | −0.0012 (17) | 0.0031 (14) | −0.0011 (18) |
C22 | 0.050 (10) | 0.012 (6) | 0.013 (6) | −0.003 (6) | 0.004 (6) | −0.002 (5) |
C23 | 0.066 (10) | 0.021 (6) | 0.029 (7) | −0.010 (6) | 0.017 (6) | 0.001 (5) |
C24 | 0.065 (13) | 0.042 (10) | 0.023 (7) | −0.033 (10) | 0.010 (8) | 0.002 (6) |
C25 | 0.030 (7) | 0.029 (9) | 0.025 (6) | −0.021 (7) | −0.003 (5) | 0.006 (7) |
C26 | 0.027 (6) | 0.028 (8) | 0.017 (6) | 0.006 (6) | 0.005 (5) | 0.002 (5) |
Br1—C16 | 1.893 (5) | C10—C11 | 1.393 (4) |
Br2—C26 | 1.849 (8) | C10—H10 | 0.9500 |
S1—O7 | 1.4284 (18) | C11—C12 | 1.399 (4) |
S1—O3 | 1.4328 (18) | C11—C14 | 1.509 (4) |
S1—N1 | 1.700 (2) | C12—C13 | 1.384 (4) |
S1—C1 | 1.754 (2) | C12—H12 | 0.9500 |
S2—O4 | 1.4271 (18) | C13—H13 | 0.9500 |
S2—O2 | 1.4310 (18) | C14—H14A | 0.9800 |
S2—N1 | 1.688 (2) | C14—H14B | 0.9800 |
S2—C8 | 1.755 (2) | C14—H14C | 0.9800 |
N1—C15 | 1.431 (4) | C15—C20 | 1.386 (7) |
N1—C21 | 1.475 (8) | C15—C16 | 1.399 (8) |
C1—C6 | 1.389 (3) | C16—C17 | 1.394 (7) |
C1—C2 | 1.391 (3) | C17—C18 | 1.385 (7) |
C2—C3 | 1.393 (3) | C17—H17 | 0.9500 |
C2—H2 | 0.9500 | C18—C19 | 1.382 (7) |
C3—C4 | 1.393 (4) | C18—H18 | 0.9500 |
C3—H3 | 0.9500 | C19—C20 | 1.385 (6) |
C4—C5 | 1.395 (3) | C19—H19 | 0.9500 |
C4—C7 | 1.504 (3) | C20—H20 | 0.9500 |
C5—C6 | 1.384 (3) | C21—C22 | 1.3900 |
C5—H5 | 0.9500 | C21—C26 | 1.3900 |
C6—H6 | 0.9500 | C22—C23 | 1.3900 |
C7—H7A | 0.9800 | C22—H22 | 0.9500 |
C7—H7B | 0.9800 | C23—C24 | 1.3900 |
C7—H7C | 0.9800 | C23—H23 | 0.9500 |
C8—C13 | 1.390 (4) | C24—C25 | 1.3900 |
C8—C9 | 1.393 (3) | C24—H24 | 0.9500 |
C9—C10 | 1.385 (4) | C25—C26 | 1.3900 |
C9—H9 | 0.9500 | C25—H25 | 0.9500 |
O7—S1—O3 | 120.57 (11) | C10—C11—C12 | 118.4 (2) |
O7—S1—N1 | 103.36 (10) | C10—C11—C14 | 120.4 (2) |
O3—S1—N1 | 108.33 (10) | C12—C11—C14 | 121.1 (3) |
O7—S1—C1 | 108.94 (11) | C13—C12—C11 | 121.3 (3) |
O3—S1—C1 | 107.99 (11) | C13—C12—H12 | 119.4 |
N1—S1—C1 | 106.86 (10) | C11—C12—H12 | 119.4 |
O4—S2—O2 | 120.62 (11) | C12—C13—C8 | 118.9 (2) |
O4—S2—N1 | 105.45 (10) | C12—C13—H13 | 120.5 |
O2—S2—N1 | 105.73 (10) | C8—C13—H13 | 120.5 |
O4—S2—C8 | 109.51 (11) | C11—C14—H14A | 109.5 |
O2—S2—C8 | 108.59 (11) | C11—C14—H14B | 109.5 |
N1—S2—C8 | 105.90 (11) | H14A—C14—H14B | 109.5 |
C15—N1—C21 | 12.1 (5) | C11—C14—H14C | 109.5 |
C15—N1—S2 | 118.3 (2) | H14A—C14—H14C | 109.5 |
C21—N1—S2 | 120.7 (6) | H14B—C14—H14C | 109.5 |
C15—N1—S1 | 119.6 (2) | C20—C15—C16 | 119.5 (4) |
C21—N1—S1 | 114.9 (6) | C20—C15—N1 | 119.7 (5) |
S2—N1—S1 | 121.89 (12) | C16—C15—N1 | 120.7 (5) |
C6—C1—C2 | 121.3 (2) | C17—C16—C15 | 120.2 (5) |
C6—C1—S1 | 119.23 (18) | C17—C16—Br1 | 118.4 (4) |
C2—C1—S1 | 119.32 (18) | C15—C16—Br1 | 121.4 (4) |
C1—C2—C3 | 118.8 (2) | C18—C17—C16 | 119.0 (4) |
C1—C2—H2 | 120.6 | C18—C17—H17 | 120.5 |
C3—C2—H2 | 120.6 | C16—C17—H17 | 120.5 |
C4—C3—C2 | 120.7 (2) | C19—C18—C17 | 121.0 (4) |
C4—C3—H3 | 119.7 | C19—C18—H18 | 119.5 |
C2—C3—H3 | 119.7 | C17—C18—H18 | 119.5 |
C3—C4—C5 | 119.1 (2) | C18—C19—C20 | 119.8 (4) |
C3—C4—C7 | 119.8 (2) | C18—C19—H19 | 120.1 |
C5—C4—C7 | 121.0 (2) | C20—C19—H19 | 120.1 |
C6—C5—C4 | 121.0 (2) | C19—C20—C15 | 120.3 (4) |
C6—C5—H5 | 119.5 | C19—C20—H20 | 119.9 |
C4—C5—H5 | 119.5 | C15—C20—H20 | 119.9 |
C5—C6—C1 | 119.0 (2) | C22—C21—C26 | 120.0 |
C5—C6—H6 | 120.5 | C22—C21—N1 | 120.5 (7) |
C1—C6—H6 | 120.5 | C26—C21—N1 | 119.2 (7) |
C4—C7—H7A | 109.5 | C23—C22—C21 | 120.0 |
C4—C7—H7B | 109.5 | C23—C22—H22 | 120.0 |
H7A—C7—H7B | 109.5 | C21—C22—H22 | 120.0 |
C4—C7—H7C | 109.5 | C22—C23—C24 | 120.0 |
H7A—C7—H7C | 109.5 | C22—C23—H23 | 120.0 |
H7B—C7—H7C | 109.5 | C24—C23—H23 | 120.0 |
C13—C8—C9 | 121.0 (2) | C23—C24—C25 | 120.0 |
C13—C8—S2 | 120.03 (19) | C23—C24—H24 | 120.0 |
C9—C8—S2 | 118.86 (19) | C25—C24—H24 | 120.0 |
C10—C9—C8 | 119.0 (2) | C26—C25—C24 | 120.0 |
C10—C9—H9 | 120.5 | C26—C25—H25 | 120.0 |
C8—C9—H9 | 120.5 | C24—C25—H25 | 120.0 |
C9—C10—C11 | 121.2 (2) | C25—C26—C21 | 120.0 |
C9—C10—H10 | 119.4 | C25—C26—Br2 | 118.7 (6) |
C11—C10—H10 | 119.4 | C21—C26—Br2 | 121.3 (6) |
O4—S2—N1—C15 | −162.2 (3) | C8—C9—C10—C11 | 0.6 (4) |
O2—S2—N1—C15 | −33.4 (4) | C9—C10—C11—C12 | −2.3 (4) |
C8—S2—N1—C15 | 81.8 (3) | C9—C10—C11—C14 | 175.6 (3) |
O4—S2—N1—C21 | −175.9 (5) | C10—C11—C12—C13 | 2.1 (4) |
O2—S2—N1—C21 | −47.0 (5) | C14—C11—C12—C13 | −175.9 (3) |
C8—S2—N1—C21 | 68.1 (5) | C11—C12—C13—C8 | 0.0 (4) |
O4—S2—N1—S1 | 23.07 (16) | C9—C8—C13—C12 | −1.8 (4) |
O2—S2—N1—S1 | 151.89 (13) | S2—C8—C13—C12 | 175.3 (2) |
C8—S2—N1—S1 | −92.98 (15) | C21—N1—C15—C20 | −167 (4) |
O7—S1—N1—C15 | −1.2 (4) | S2—N1—C15—C20 | 88.1 (4) |
O3—S1—N1—C15 | −130.2 (3) | S1—N1—C15—C20 | −97.1 (4) |
C1—S1—N1—C15 | 113.7 (3) | C21—N1—C15—C16 | 10 (3) |
O7—S1—N1—C21 | 11.4 (5) | S2—N1—C15—C16 | −95.3 (4) |
O3—S1—N1—C21 | −117.6 (5) | S1—N1—C15—C16 | 79.5 (4) |
C1—S1—N1—C21 | 126.2 (5) | C20—C15—C16—C17 | −4.2 (6) |
O7—S1—N1—S2 | 173.46 (13) | N1—C15—C16—C17 | 179.2 (5) |
O3—S1—N1—S2 | 44.46 (16) | C20—C15—C16—Br1 | 175.9 (4) |
C1—S1—N1—S2 | −71.67 (16) | N1—C15—C16—Br1 | −0.7 (6) |
O7—S1—C1—C6 | −145.08 (19) | C15—C16—C17—C18 | 3.3 (7) |
O3—S1—C1—C6 | −12.5 (2) | Br1—C16—C17—C18 | −176.8 (4) |
N1—S1—C1—C6 | 103.9 (2) | C16—C17—C18—C19 | −0.1 (7) |
O7—S1—C1—C2 | 31.2 (2) | C17—C18—C19—C20 | −2.3 (8) |
O3—S1—C1—C2 | 163.77 (19) | C18—C19—C20—C15 | 1.4 (7) |
N1—S1—C1—C2 | −79.9 (2) | C16—C15—C20—C19 | 1.8 (6) |
C6—C1—C2—C3 | 0.5 (4) | N1—C15—C20—C19 | 178.5 (4) |
S1—C1—C2—C3 | −175.65 (19) | C15—N1—C21—C22 | −159 (4) |
C1—C2—C3—C4 | 0.8 (4) | S2—N1—C21—C22 | −77.5 (7) |
C2—C3—C4—C5 | −1.4 (4) | S1—N1—C21—C22 | 84.8 (7) |
C2—C3—C4—C7 | 177.8 (2) | C15—N1—C21—C26 | 14 (3) |
C3—C4—C5—C6 | 0.8 (4) | S2—N1—C21—C26 | 95.9 (7) |
C7—C4—C5—C6 | −178.5 (2) | S1—N1—C21—C26 | −101.7 (6) |
C4—C5—C6—C1 | 0.5 (4) | C26—C21—C22—C23 | 0.0 |
C2—C1—C6—C5 | −1.2 (4) | N1—C21—C22—C23 | 173.4 (11) |
S1—C1—C6—C5 | 174.99 (19) | C21—C22—C23—C24 | 0.0 |
O4—S2—C8—C13 | 151.7 (2) | C22—C23—C24—C25 | 0.0 |
O2—S2—C8—C13 | 18.1 (3) | C23—C24—C25—C26 | 0.0 |
N1—S2—C8—C13 | −95.1 (2) | C24—C25—C26—C21 | 0.0 |
O4—S2—C8—C9 | −31.2 (2) | C24—C25—C26—Br2 | −179.5 (8) |
O2—S2—C8—C9 | −164.8 (2) | C22—C21—C26—C25 | 0.0 |
N1—S2—C8—C9 | 82.1 (2) | N1—C21—C26—C25 | −173.5 (11) |
C13—C8—C9—C10 | 1.6 (4) | C22—C21—C26—Br2 | 179.5 (8) |
S2—C8—C9—C10 | −175.6 (2) | N1—C21—C26—Br2 | 6.0 (8) |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O3i | 0.95 | 2.45 | 3.199 (3) | 135 |
Symmetry code: (i) −x+1, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C20H18BrNO4S2 |
Mr | 480.38 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 100 |
a, b, c (Å) | 10.5819 (15), 13.1465 (19), 14.235 (2) |
β (°) | 95.478 (2) |
V (Å3) | 1971.2 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 2.32 |
Crystal size (mm) | 0.38 × 0.33 × 0.24 |
Data collection | |
Diffractometer | Bruker KAPPA APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2001) |
Tmin, Tmax | 0.472, 0.605 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 23193, 4792, 4320 |
Rint | 0.031 |
(sin θ/λ)max (Å−1) | 0.666 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.085, 1.24 |
No. of reflections | 4792 |
No. of parameters | 301 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.52, −0.53 |
Computer programs: APEX2 (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and X-SEED (Barbour, 2001), WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O3i | 0.95 | 2.45 | 3.199 (3) | 135.3 |
Symmetry code: (i) −x+1, y+1/2, −z+1/2. |
O-Bromoaryl sulfonamides have been used for intramolecular arylation via palladium catalysis (Ames & Opalko, 1984). Herein, we report the crystal structure of the title compound which was synthesised as a precursor of cyclic sultams (Arshad et al., 2011).
The N-atom of O-bromoaniline is directly attached to two p-toluene sulfonyl moieties. The interesting feature in the crystal structure is that bromobenzene group is disordered over two positions (C15—C20/Br1) and (C21—C26/Br2) with the occupancy of 0.74 and 0.26, respectively. The dihedral angle between the two disordered parts of the ring is 6.6 (6)°. The two toluene rings (C1—C7) & (C8—C14) are oriented at dihedral angle of 45.34 (89)°. The part (C15—C20/Br1) of bromobenzene ring formed dihedral angles of 24.0 (2)° and 38.77 (11)° with both of the toluene rings (C1—C7) & (C8—C14,) respectively, while the other part is oriented at dihedral angles of 19.6 (6)° and 34.8 (2)° with respect to the toluene rings. No classical hydrogen bonding has been observed in the molecule, only C—H···O type interactions connect the molecules in a zig-zag mode (Fig. 2 and Tab. 1).