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In the title compound, C20H18BrNO4S2, the mean planes formed by the toluene substituents are inclined at a dihedral angle of 45.34 (8)°. The bromo­benzene group is disordered over two positions with an occupancy ratio of 0.74:0.26, resulting in two conformations of the ring; the two rings are oriented at a dihedral angle of 6.6 (6)° with each other. In the crystal structure, weak C—H...O inter­actions connect the mol­ecules in a zigzag manner along the a axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536811032533/pv2443sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536811032533/pv2443Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S1600536811032533/pv2443Isup3.cml
Supplementary material

CCDC reference: 845406

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](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

Comment top

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).

Related literature top

For general background, see: Ames & Opalko (1984); Arshad et al. (2011). For related crystal structures, see: Zhao et al. (2007); Song (2008); Hanson & Hitchcock (2004).

Experimental top

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.

Refinement top

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

Computing details top

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).

Figures top
[Figure 1] Fig. 1. An ORTEP diagram of the title compound with thermal ellipsoids drawn at the 50% probability level; smaller fraction of the disordered bromobenzene ring has been plotted with dashed lines.
[Figure 2] Fig. 2. Unit cell packing for the title compound showing weak C—H···O interactions as dashed lines.
N-(2-Bromophenyl)-4-methyl-N- (4-methylphenylsulfonyl)benzenesulfonamide top
Crystal data top
C20H18BrNO4S2F(000) = 976
Mr = 480.38Dx = 1.679 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9904 reflections
a = 10.5819 (15) Åθ = 2.3–28.1°
b = 13.1465 (19) ŵ = 2.32 mm1
c = 14.235 (2) ÅT = 100 K
β = 95.478 (2)°Blocks, colorless
V = 1971.2 (5) Å30.38 × 0.33 × 0.24 mm
Z = 4
Data collection top
Bruker KAPPA APEXII CCD
diffractometer
4792 independent reflections
Radiation source: fine-focus sealed tube4320 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
ϕ and ω scansθmax = 28.3°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 1413
Tmin = 0.472, Tmax = 0.605k = 1717
23193 measured reflectionsl = 1818
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085H-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 parametersΔρmax = 0.52 e Å3
0 restraintsΔρmin = 0.53 e Å3
Crystal data top
C20H18BrNO4S2V = 1971.2 (5) Å3
Mr = 480.38Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.5819 (15) ŵ = 2.32 mm1
b = 13.1465 (19) ÅT = 100 K
c = 14.235 (2) Å0.38 × 0.33 × 0.24 mm
β = 95.478 (2)°
Data collection top
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 = 0.605Rint = 0.031
23193 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.085H-atom parameters constrained
S = 1.24Δρmax = 0.52 e Å3
4792 reflectionsΔρmin = 0.53 e Å3
301 parameters
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. 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Br10.25875 (4)0.31399 (3)0.20992 (2)0.02691 (9)0.74
Br20.06672 (10)0.62953 (9)0.15927 (9)0.0346 (3)0.26
S10.30298 (5)0.58728 (4)0.18802 (4)0.01811 (12)
S20.19193 (5)0.55064 (5)0.36828 (4)0.01938 (12)
O20.06261 (16)0.55206 (14)0.38987 (12)0.0240 (4)
O30.42299 (16)0.56000 (13)0.23665 (13)0.0239 (4)
O40.27382 (16)0.63481 (13)0.39241 (12)0.0236 (4)
O70.26821 (17)0.55219 (13)0.09413 (12)0.0237 (4)
N10.18608 (18)0.54032 (15)0.24974 (13)0.0180 (4)
C10.2899 (2)0.72024 (17)0.19019 (17)0.0185 (4)
C20.1987 (2)0.76797 (19)0.12845 (17)0.0214 (5)
H20.14010.72900.08850.026*
C30.1949 (2)0.87387 (19)0.12623 (18)0.0225 (5)
H30.13240.90740.08500.027*
C40.2817 (2)0.93112 (18)0.18389 (17)0.0206 (5)
C50.3712 (2)0.88108 (18)0.24575 (18)0.0219 (5)
H50.42990.91970.28580.026*
C60.3756 (2)0.77596 (19)0.24962 (17)0.0216 (5)
H60.43630.74240.29230.026*
C70.2787 (2)1.04533 (19)0.1779 (2)0.0261 (5)
H7A0.33301.06800.12980.039*
H7B0.31001.07430.23920.039*
H7C0.19141.06810.16070.039*
C80.2633 (2)0.43825 (19)0.41368 (17)0.0220 (5)
C90.3953 (2)0.4307 (2)0.42161 (17)0.0236 (5)
H90.44580.48720.40690.028*
C100.4515 (2)0.3396 (2)0.45122 (18)0.0264 (5)
H100.54150.33420.45730.032*
C110.3788 (3)0.2558 (2)0.47224 (19)0.0291 (6)
C120.2467 (3)0.2666 (2)0.4662 (2)0.0335 (6)
H120.19600.21070.48230.040*
C130.1884 (3)0.3570 (2)0.4371 (2)0.0295 (6)
H130.09860.36340.43330.035*
C140.4414 (3)0.1552 (2)0.4977 (2)0.0378 (7)
H14A0.38710.11550.53610.057*
H14B0.52380.16700.53350.057*
H14C0.45380.11750.43990.057*
C150.0847 (5)0.4829 (4)0.2018 (3)0.0202 (11)0.74
C160.1015 (5)0.3805 (4)0.1793 (4)0.0237 (10)0.74
C170.0016 (5)0.3249 (3)0.1337 (3)0.0275 (9)0.74
H170.01120.25450.12130.033*0.74
C180.1120 (5)0.3739 (5)0.1067 (3)0.0291 (10)0.74
H180.18050.33650.07550.035*0.74
C190.1272 (4)0.4763 (4)0.1243 (3)0.0275 (9)0.74
H190.20450.50950.10330.033*0.74
C200.0293 (5)0.5305 (4)0.1728 (3)0.0213 (9)0.74
H200.04040.60050.18620.026*0.74
C210.1025 (10)0.4648 (7)0.1985 (9)0.012 (4)*0.26
C220.1370 (9)0.3627 (8)0.1979 (8)0.025 (4)0.26
H220.21860.34220.22490.030*0.26
C230.0520 (12)0.2907 (6)0.1578 (7)0.038 (3)0.26
H230.07560.22100.15740.046*0.26
C240.0673 (11)0.3207 (8)0.1183 (6)0.043 (4)0.26
H240.12540.27150.09090.052*0.26
C250.1018 (8)0.4227 (9)0.1189 (7)0.028 (3)0.26
H250.18340.44320.09190.034*0.26
C260.0169 (10)0.4947 (6)0.1590 (8)0.024 (3)0.26
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.03615 (19)0.01695 (15)0.02757 (18)0.00531 (14)0.00269 (14)0.00062 (13)
Br20.0257 (5)0.0338 (6)0.0445 (6)0.0085 (4)0.0044 (4)0.0156 (5)
S10.0176 (3)0.0155 (3)0.0215 (3)0.0006 (2)0.0035 (2)0.0015 (2)
S20.0177 (3)0.0218 (3)0.0185 (3)0.0002 (2)0.0010 (2)0.0017 (2)
O20.0198 (8)0.0302 (9)0.0221 (9)0.0010 (7)0.0028 (7)0.0013 (7)
O30.0193 (8)0.0196 (8)0.0327 (10)0.0025 (7)0.0020 (7)0.0044 (7)
O40.0249 (9)0.0241 (9)0.0215 (9)0.0024 (7)0.0003 (7)0.0010 (7)
O70.0282 (9)0.0207 (8)0.0232 (9)0.0016 (7)0.0069 (7)0.0007 (7)
N10.0181 (9)0.0184 (9)0.0175 (9)0.0026 (8)0.0016 (7)0.0001 (7)
C10.0197 (11)0.0141 (10)0.0220 (11)0.0007 (8)0.0037 (9)0.0023 (9)
C20.0208 (11)0.0214 (12)0.0216 (12)0.0004 (9)0.0008 (9)0.0015 (9)
C30.0208 (11)0.0221 (12)0.0247 (12)0.0034 (9)0.0026 (9)0.0065 (9)
C40.0199 (11)0.0166 (11)0.0267 (12)0.0008 (9)0.0094 (9)0.0033 (9)
C50.0201 (11)0.0199 (11)0.0256 (12)0.0042 (9)0.0022 (9)0.0005 (9)
C60.0199 (11)0.0213 (12)0.0233 (12)0.0000 (9)0.0001 (9)0.0046 (9)
C70.0249 (12)0.0175 (11)0.0367 (14)0.0030 (9)0.0072 (11)0.0042 (10)
C80.0204 (11)0.0246 (12)0.0207 (11)0.0016 (9)0.0002 (9)0.0067 (9)
C90.0211 (12)0.0281 (13)0.0212 (12)0.0026 (10)0.0007 (9)0.0044 (10)
C100.0217 (12)0.0341 (14)0.0231 (12)0.0026 (10)0.0009 (10)0.0049 (10)
C110.0308 (14)0.0323 (14)0.0249 (13)0.0049 (11)0.0058 (11)0.0100 (11)
C120.0281 (14)0.0325 (15)0.0412 (16)0.0007 (11)0.0094 (12)0.0171 (12)
C130.0215 (12)0.0332 (14)0.0340 (14)0.0008 (11)0.0047 (11)0.0121 (12)
C140.0371 (16)0.0335 (15)0.0436 (17)0.0088 (13)0.0087 (13)0.0165 (13)
C150.024 (2)0.0188 (18)0.019 (2)0.0033 (19)0.0044 (16)0.0018 (15)
C160.029 (2)0.023 (2)0.020 (2)0.0013 (18)0.0029 (18)0.0049 (17)
C170.040 (3)0.018 (2)0.025 (2)0.011 (2)0.006 (2)0.0035 (16)
C180.032 (3)0.033 (3)0.022 (2)0.017 (2)0.0014 (17)0.004 (2)
C190.024 (2)0.035 (2)0.0238 (19)0.0046 (18)0.0000 (14)0.0022 (19)
C200.0201 (19)0.026 (3)0.018 (2)0.0012 (17)0.0031 (14)0.0011 (18)
C220.050 (10)0.012 (6)0.013 (6)0.003 (6)0.004 (6)0.002 (5)
C230.066 (10)0.021 (6)0.029 (7)0.010 (6)0.017 (6)0.001 (5)
C240.065 (13)0.042 (10)0.023 (7)0.033 (10)0.010 (8)0.002 (6)
C250.030 (7)0.029 (9)0.025 (6)0.021 (7)0.003 (5)0.006 (7)
C260.027 (6)0.028 (8)0.017 (6)0.006 (6)0.005 (5)0.002 (5)
Geometric parameters (Å, º) top
Br1—C161.893 (5)C10—C111.393 (4)
Br2—C261.849 (8)C10—H100.9500
S1—O71.4284 (18)C11—C121.399 (4)
S1—O31.4328 (18)C11—C141.509 (4)
S1—N11.700 (2)C12—C131.384 (4)
S1—C11.754 (2)C12—H120.9500
S2—O41.4271 (18)C13—H130.9500
S2—O21.4310 (18)C14—H14A0.9800
S2—N11.688 (2)C14—H14B0.9800
S2—C81.755 (2)C14—H14C0.9800
N1—C151.431 (4)C15—C201.386 (7)
N1—C211.475 (8)C15—C161.399 (8)
C1—C61.389 (3)C16—C171.394 (7)
C1—C21.391 (3)C17—C181.385 (7)
C2—C31.393 (3)C17—H170.9500
C2—H20.9500C18—C191.382 (7)
C3—C41.393 (4)C18—H180.9500
C3—H30.9500C19—C201.385 (6)
C4—C51.395 (3)C19—H190.9500
C4—C71.504 (3)C20—H200.9500
C5—C61.384 (3)C21—C221.3900
C5—H50.9500C21—C261.3900
C6—H60.9500C22—C231.3900
C7—H7A0.9800C22—H220.9500
C7—H7B0.9800C23—C241.3900
C7—H7C0.9800C23—H230.9500
C8—C131.390 (4)C24—C251.3900
C8—C91.393 (3)C24—H240.9500
C9—C101.385 (4)C25—C261.3900
C9—H90.9500C25—H250.9500
O7—S1—O3120.57 (11)C10—C11—C12118.4 (2)
O7—S1—N1103.36 (10)C10—C11—C14120.4 (2)
O3—S1—N1108.33 (10)C12—C11—C14121.1 (3)
O7—S1—C1108.94 (11)C13—C12—C11121.3 (3)
O3—S1—C1107.99 (11)C13—C12—H12119.4
N1—S1—C1106.86 (10)C11—C12—H12119.4
O4—S2—O2120.62 (11)C12—C13—C8118.9 (2)
O4—S2—N1105.45 (10)C12—C13—H13120.5
O2—S2—N1105.73 (10)C8—C13—H13120.5
O4—S2—C8109.51 (11)C11—C14—H14A109.5
O2—S2—C8108.59 (11)C11—C14—H14B109.5
N1—S2—C8105.90 (11)H14A—C14—H14B109.5
C15—N1—C2112.1 (5)C11—C14—H14C109.5
C15—N1—S2118.3 (2)H14A—C14—H14C109.5
C21—N1—S2120.7 (6)H14B—C14—H14C109.5
C15—N1—S1119.6 (2)C20—C15—C16119.5 (4)
C21—N1—S1114.9 (6)C20—C15—N1119.7 (5)
S2—N1—S1121.89 (12)C16—C15—N1120.7 (5)
C6—C1—C2121.3 (2)C17—C16—C15120.2 (5)
C6—C1—S1119.23 (18)C17—C16—Br1118.4 (4)
C2—C1—S1119.32 (18)C15—C16—Br1121.4 (4)
C1—C2—C3118.8 (2)C18—C17—C16119.0 (4)
C1—C2—H2120.6C18—C17—H17120.5
C3—C2—H2120.6C16—C17—H17120.5
C4—C3—C2120.7 (2)C19—C18—C17121.0 (4)
C4—C3—H3119.7C19—C18—H18119.5
C2—C3—H3119.7C17—C18—H18119.5
C3—C4—C5119.1 (2)C18—C19—C20119.8 (4)
C3—C4—C7119.8 (2)C18—C19—H19120.1
C5—C4—C7121.0 (2)C20—C19—H19120.1
C6—C5—C4121.0 (2)C19—C20—C15120.3 (4)
C6—C5—H5119.5C19—C20—H20119.9
C4—C5—H5119.5C15—C20—H20119.9
C5—C6—C1119.0 (2)C22—C21—C26120.0
C5—C6—H6120.5C22—C21—N1120.5 (7)
C1—C6—H6120.5C26—C21—N1119.2 (7)
C4—C7—H7A109.5C23—C22—C21120.0
C4—C7—H7B109.5C23—C22—H22120.0
H7A—C7—H7B109.5C21—C22—H22120.0
C4—C7—H7C109.5C22—C23—C24120.0
H7A—C7—H7C109.5C22—C23—H23120.0
H7B—C7—H7C109.5C24—C23—H23120.0
C13—C8—C9121.0 (2)C23—C24—C25120.0
C13—C8—S2120.03 (19)C23—C24—H24120.0
C9—C8—S2118.86 (19)C25—C24—H24120.0
C10—C9—C8119.0 (2)C26—C25—C24120.0
C10—C9—H9120.5C26—C25—H25120.0
C8—C9—H9120.5C24—C25—H25120.0
C9—C10—C11121.2 (2)C25—C26—C21120.0
C9—C10—H10119.4C25—C26—Br2118.7 (6)
C11—C10—H10119.4C21—C26—Br2121.3 (6)
O4—S2—N1—C15162.2 (3)C8—C9—C10—C110.6 (4)
O2—S2—N1—C1533.4 (4)C9—C10—C11—C122.3 (4)
C8—S2—N1—C1581.8 (3)C9—C10—C11—C14175.6 (3)
O4—S2—N1—C21175.9 (5)C10—C11—C12—C132.1 (4)
O2—S2—N1—C2147.0 (5)C14—C11—C12—C13175.9 (3)
C8—S2—N1—C2168.1 (5)C11—C12—C13—C80.0 (4)
O4—S2—N1—S123.07 (16)C9—C8—C13—C121.8 (4)
O2—S2—N1—S1151.89 (13)S2—C8—C13—C12175.3 (2)
C8—S2—N1—S192.98 (15)C21—N1—C15—C20167 (4)
O7—S1—N1—C151.2 (4)S2—N1—C15—C2088.1 (4)
O3—S1—N1—C15130.2 (3)S1—N1—C15—C2097.1 (4)
C1—S1—N1—C15113.7 (3)C21—N1—C15—C1610 (3)
O7—S1—N1—C2111.4 (5)S2—N1—C15—C1695.3 (4)
O3—S1—N1—C21117.6 (5)S1—N1—C15—C1679.5 (4)
C1—S1—N1—C21126.2 (5)C20—C15—C16—C174.2 (6)
O7—S1—N1—S2173.46 (13)N1—C15—C16—C17179.2 (5)
O3—S1—N1—S244.46 (16)C20—C15—C16—Br1175.9 (4)
C1—S1—N1—S271.67 (16)N1—C15—C16—Br10.7 (6)
O7—S1—C1—C6145.08 (19)C15—C16—C17—C183.3 (7)
O3—S1—C1—C612.5 (2)Br1—C16—C17—C18176.8 (4)
N1—S1—C1—C6103.9 (2)C16—C17—C18—C190.1 (7)
O7—S1—C1—C231.2 (2)C17—C18—C19—C202.3 (8)
O3—S1—C1—C2163.77 (19)C18—C19—C20—C151.4 (7)
N1—S1—C1—C279.9 (2)C16—C15—C20—C191.8 (6)
C6—C1—C2—C30.5 (4)N1—C15—C20—C19178.5 (4)
S1—C1—C2—C3175.65 (19)C15—N1—C21—C22159 (4)
C1—C2—C3—C40.8 (4)S2—N1—C21—C2277.5 (7)
C2—C3—C4—C51.4 (4)S1—N1—C21—C2284.8 (7)
C2—C3—C4—C7177.8 (2)C15—N1—C21—C2614 (3)
C3—C4—C5—C60.8 (4)S2—N1—C21—C2695.9 (7)
C7—C4—C5—C6178.5 (2)S1—N1—C21—C26101.7 (6)
C4—C5—C6—C10.5 (4)C26—C21—C22—C230.0
C2—C1—C6—C51.2 (4)N1—C21—C22—C23173.4 (11)
S1—C1—C6—C5174.99 (19)C21—C22—C23—C240.0
O4—S2—C8—C13151.7 (2)C22—C23—C24—C250.0
O2—S2—C8—C1318.1 (3)C23—C24—C25—C260.0
N1—S2—C8—C1395.1 (2)C24—C25—C26—C210.0
O4—S2—C8—C931.2 (2)C24—C25—C26—Br2179.5 (8)
O2—S2—C8—C9164.8 (2)C22—C21—C26—C250.0
N1—S2—C8—C982.1 (2)N1—C21—C26—C25173.5 (11)
C13—C8—C9—C101.6 (4)C22—C21—C26—Br2179.5 (8)
S2—C8—C9—C10175.6 (2)N1—C21—C26—Br26.0 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5···O3i0.952.453.199 (3)135
Symmetry code: (i) x+1, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC20H18BrNO4S2
Mr480.38
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)10.5819 (15), 13.1465 (19), 14.235 (2)
β (°) 95.478 (2)
V3)1971.2 (5)
Z4
Radiation typeMo Kα
µ (mm1)2.32
Crystal size (mm)0.38 × 0.33 × 0.24
Data collection
DiffractometerBruker KAPPA APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2001)
Tmin, Tmax0.472, 0.605
No. of measured, independent and
observed [I > 2σ(I)] reflections
23193, 4792, 4320
Rint0.031
(sin θ/λ)max1)0.666
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.085, 1.24
No. of reflections4792
No. of parameters301
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5···O3i0.952.453.199 (3)135.3
Symmetry code: (i) x+1, y+1/2, z+1/2.
 

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