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The title compound, C22H18Br2N2O2S, crystallizes in the centrosymmetric space group P\overline 1 with two mol­ecules in the asymmetric unit. The two crystallographically independent mol­ecules differ in the orientation of the aniline substituent with respect to the indole moiety. In both mol­ecules, the S atom shows a distorted tetrahedral geometry. The molecular structure is stabilized by C—H...O, N—H...O, N—H...Br and C—H...π intramolecular interactions and the molecular packing is stabilized by C—H...Br, C—H...O and C—H...π interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802023322/ci6189sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802023322/ci6189Isup2.hkl
Contains datablock I

CCDC reference: 204696

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.014 Å
  • R factor = 0.056
  • wR factor = 0.135
  • Data-to-parameter ratio = 13.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes

ABSTM_02 When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.797 Tmax scaled 0.306 Tmin scaled 0.240

Comment top

Indoles have been of interest for many years, since a large number of natural products contain these heterocyclic nuclei and they are found in numerous commercial products including pharmaceuticals, fragrances and dyes (Padwa et al., 1999). These type of compounds are also used as antimicrobial and anti-inflammatory agents (El-Sayed et al., 1986). Sulfonamide-containing drugs behave as diuretics (Crawford & Kenedy, 1959; Cameron & Cameron, 1975). Investigations using spectroscopic methods have revealed the DNA-binding activity of the indole molecule (Sivaraman et al., 1996). The indole ring system is also found to occur in plants (Nigovic' et al., 2000); for example, indole-3-acetic acid is a naturally occurring plant-growth harmone that controls several plant-growth activities (Moore, 1989; Fargasova, 1994). Against this background, and in order to obtain detailed information of its molecular conformation in the solid state, X-ray studies on the title compound, (I), were carried out.

The asymmetric unit of (I) consists of two crystallographically independent molecules, viz. A and B. The corresponding bond lengths and angles of A and B agree with each other, but the orientation of aniline substituent with respect to the indole moiety in A is different from that in B. This can be seen from the N1—C8—C9—N2 and C8—C9—N2—C10 torsion angles of 95.5 (8) [−60.5 (10)° in B] and 176.5 (6)° [−83.2 (9)°], respectively. The geometry of molecule A agrees with that of a closely related molecule, namely 2-bromo-N-[3-bromo-N-(phenylsulfonyl)indol-2-ylmethyl]aniline, (II) (Govind et al., 2002).

The torsion angles O2—S1—N1—C1 [−46.0 (6) and −48.2 (6)° in A and B] and O2—S1—C17—C22 [−156.1 (6) and −164.8 (6)°] describe the conformation of the phenylsulfonyl group with respect to the indole moiety; the mean plane through the indole moiety and the phenyl ring bound to the sulfonyl group form a dihedral angle of 84.8 (4)° in molecule A and 86.5 (4)° in molecule B. In A, the phenyl ring of the aniline substituent forms a dihedral angle of 84.9 (4)° with the indole moiety, while in B this value is 77.8 (4)°. In both molecules, the S atom is in a distorted tetrahedral configuration. As reported previously for related phenylsulfonylindole derivatives (Sankaranarayanan et al., 2001; Govind et al., 2002; Seshadri et al., 2002), significant distortion from the ideal value is observed for O—S—O and N—S—C angles (Table 1). The relatively large values of the C—N distances in the indole moiety are due to the electron-withdrawing character of the phenylsulfonyl group. The molecular structure is stabilized by C—H···O, N—H···O, N—H···Br and C—H···π intramolecular interactions (Table 2). The observed intramolecular interactions are similar to those reported for (II) (Govind et al., 2002). A short Br···Br contact of 3.500 (2) Å is observed between atoms Br2A and Br1B. The molecular packing in the crystal is stabilized by C—H···Br, C—H···O and C—H···π interactions. In Table 2, Cg(PS) denotes the phenyl ring bound to the sulfonyl group and Cg(PA) denotes that of the aniline substituent.

Experimental top

A solution of 1-phenylsulfonyl-2-bromomethyl-2-bromoindole (4.29 g, 10 mmol) and 2-bromo-4-methylaniline (2 equivalents) in dry DMF (25 ml) containing finely powdered K2CO3 (200 mg) was stirred at room temperature for 12 h. The reaction mixture was then poured on to ice (200 g) and the solid formed was filtered off immediately and washed with an excess of water. The crude product was dried over CaCl2 and recrystallized from ethyl acetate–hexane (1:9) to give colourless crystals of the title compound.

Refinement top

All the H atoms were fixed geometrically and allowed to ride on the corresponding non-H atoms. Owing to the poor diffraction quality of the crystal, the ratio of observed to unique reflections is low (45%).

Computing details top

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

Figures top
[Figure 1] Fig. 1. A view of the two crystallographically independent molecules in the asymmetric unit. Displacement ellipsoids are shown at the 30% probability level.
2-Bromo-N-[3-bromo-1-(phenylsulfonyl)indol-2-ylmethyl]-4-methylaniline top
Crystal data top
C22H18Br2N2O2SZ = 4
Mr = 534.26F(000) = 1064
Triclinic, P1Dx = 1.677 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71069 Å
a = 12.436 (3) ÅCell parameters from 25 reflections
b = 12.715 (3) Åθ = 1.4–25.0°
c = 16.073 (3) ŵ = 3.95 mm1
α = 70.13 (3)°T = 293 K
β = 69.23 (3)°Prism, colorless
γ = 66.22 (3)°0.40 × 0.30 × 0.30 mm
V = 2116.2 (10) Å3
Data collection top
Enraf-Nonius CA-D4
diffractometer
3320 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.053
Graphite monochromatorθmax = 25.0°, θmin = 1.4°
non–profiled ω/2θ scansh = 014
Absorption correction: ψ scan
(North et al., 1968)
k = 1315
Tmin = 0.301, Tmax = 0.384l = 1719
7786 measured reflections3 standard reflections every 300 min
7411 independent reflections intensity decay: 1%
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)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135H-atom parameters constrained
S = 0.95 w = 1/[σ2(Fo2) + (0.0576P)2]
where P = (Fo2 + 2Fc2)/3
7411 reflections(Δ/σ)max < 0.001
559 parametersΔρmax = 0.63 e Å3
0 restraintsΔρmin = 0.47 e Å3
Crystal data top
C22H18Br2N2O2Sγ = 66.22 (3)°
Mr = 534.26V = 2116.2 (10) Å3
Triclinic, P1Z = 4
a = 12.436 (3) ÅMo Kα radiation
b = 12.715 (3) ŵ = 3.95 mm1
c = 16.073 (3) ÅT = 293 K
α = 70.13 (3)°0.40 × 0.30 × 0.30 mm
β = 69.23 (3)°
Data collection top
Enraf-Nonius CA-D4
diffractometer
3320 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.053
Tmin = 0.301, Tmax = 0.3843 standard reflections every 300 min
7786 measured reflections intensity decay: 1%
7411 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0560 restraints
wR(F2) = 0.135H-atom parameters constrained
S = 0.95Δρmax = 0.63 e Å3
7411 reflectionsΔρmin = 0.47 e Å3
559 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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*/Ueq
Br1A0.50694 (8)0.02260 (7)0.32919 (6)0.0595 (3)
Br2A0.01052 (8)0.31929 (9)0.37830 (6)0.0751 (3)
S1A0.3273 (2)0.36634 (19)0.52996 (14)0.0543 (6)
O1A0.2403 (5)0.3152 (5)0.5962 (3)0.0605 (15)
O2A0.3971 (5)0.4071 (5)0.5583 (4)0.0717 (17)
N1A0.4279 (5)0.2627 (5)0.4743 (4)0.0440 (16)
N2A0.1945 (5)0.1853 (5)0.4776 (4)0.0483 (16)
H2AN0.19160.24890.43040.04 (2)*
C1A0.5354 (7)0.2803 (6)0.4075 (5)0.044 (2)
C2A0.5984 (8)0.3552 (7)0.3956 (6)0.061 (2)
H2A0.57120.40720.43570.016 (16)*
C3A0.7001 (8)0.3521 (8)0.3244 (7)0.067 (3)
H3A0.74530.40290.31510.11 (3)*
C4A0.7408 (8)0.2778 (9)0.2664 (7)0.070 (3)
H4A0.81220.27880.21700.05 (2)*
C5A0.6795 (7)0.2038 (7)0.2784 (5)0.053 (2)
H5A0.70840.15100.23870.06 (2)*
C6A0.5735 (7)0.2060 (6)0.3497 (5)0.0424 (19)
C7A0.4898 (6)0.1421 (6)0.3804 (5)0.0365 (18)
C8A0.4022 (6)0.1766 (7)0.4536 (5)0.0420 (19)
C9A0.3039 (6)0.1246 (7)0.5100 (5)0.046 (2)
H9A0.28540.12890.57230.06 (2)*
H9B0.33200.04290.50860.035 (19)*
C10A0.0944 (7)0.1457 (7)0.5185 (5)0.0424 (19)
C11A0.0924 (8)0.0534 (8)0.5954 (5)0.056 (2)
H11A0.16210.01430.62030.05 (2)*
C12A0.0081 (10)0.0168 (9)0.6369 (6)0.072 (3)
H12A0.00770.04580.69110.04 (2)*
C13A0.1096 (9)0.0676 (9)0.6034 (7)0.067 (3)
C14A0.1072 (7)0.1564 (8)0.5260 (6)0.060 (2)
H14A0.17570.19220.49970.06 (2)*
C15A0.0075 (7)0.1963 (7)0.4847 (5)0.053 (2)
C16A0.2230 (10)0.0303 (12)0.6493 (9)0.103 (4)
H16A0.21010.03280.70220.13 (5)*
H16B0.23970.00390.60730.19 (6)*
H16C0.29060.09640.66750.25 (9)*
C17A0.2608 (7)0.4782 (7)0.4482 (5)0.051 (2)
C18A0.3095 (9)0.5685 (8)0.3950 (6)0.065 (2)
H18A0.38050.57090.40430.06 (3)*
C19A0.2553 (11)0.6523 (9)0.3300 (7)0.079 (3)
H19A0.29040.71320.29240.07 (3)*
C20A0.1533 (10)0.6532 (9)0.3169 (6)0.075 (3)
H20A0.11680.71430.27080.06 (2)*
C21A0.1022 (9)0.5661 (8)0.3692 (6)0.068 (3)
H21A0.02990.56610.36030.07 (3)*
C22A0.1567 (8)0.4784 (7)0.4350 (5)0.060 (2)
H22A0.12220.41700.47190.05 (2)*
Br1B0.27014 (8)0.30022 (8)0.21782 (6)0.0677 (3)
Br2B0.46958 (8)0.20930 (9)0.23130 (6)0.0739 (3)
S1B0.71865 (18)0.16883 (19)0.03088 (14)0.0512 (6)
O1B0.6861 (5)0.0913 (5)0.0570 (4)0.0679 (16)
O2B0.7783 (5)0.2465 (5)0.0989 (3)0.0692 (17)
N1B0.5901 (5)0.2539 (5)0.0251 (4)0.0444 (16)
N2B0.4314 (6)0.1543 (6)0.0252 (5)0.0564 (18)
H2BN0.49450.12040.06740.22 (7)*
C1B0.5907 (7)0.3439 (6)0.0560 (5)0.0425 (19)
C2B0.6717 (8)0.4060 (7)0.0276 (6)0.058 (2)
H2B0.74330.39020.02160.028 (18)*
C3B0.6444 (10)0.4948 (8)0.0730 (7)0.077 (3)
H3B0.70040.53780.05480.16 (5)*
C4B0.5421 (9)0.5216 (8)0.1419 (7)0.065 (3)
H4B0.52720.58140.17210.04 (2)*
C5B0.4620 (9)0.4618 (8)0.1673 (6)0.068 (3)
H5B0.38770.48230.21340.07 (3)*
C6B0.4861 (7)0.3706 (6)0.1256 (5)0.048 (2)
C7B0.4228 (6)0.2928 (6)0.1364 (5)0.0397 (18)
C8B0.4824 (7)0.2226 (6)0.0796 (5)0.0422 (19)
C9B0.4499 (7)0.1307 (7)0.0642 (5)0.051 (2)
H9C0.37690.12250.10960.05 (2)*
H9D0.51300.05630.07370.08 (3)*
C10B0.3250 (7)0.2247 (6)0.0508 (5)0.0440 (19)
C11B0.2143 (7)0.2615 (7)0.0104 (6)0.055 (2)
H11B0.20990.23740.07470.08 (3)*
C12B0.1101 (8)0.3311 (7)0.0190 (7)0.064 (2)
H12B0.03510.35570.02540.05 (2)*
C13B0.1104 (8)0.3661 (7)0.1108 (6)0.063 (2)
C14B0.2205 (8)0.3286 (7)0.1710 (6)0.058 (2)
H14B0.22540.35030.23530.019 (16)*
C15B0.3228 (7)0.2607 (7)0.1416 (5)0.050 (2)
C16B0.0031 (9)0.4418 (11)0.1427 (8)0.093 (3)
H16D0.01470.45750.20800.36 (13)*
H16E0.03440.51510.12410.21 (8)*
H16F0.06250.40160.11540.16 (6)*
C17B0.8056 (7)0.0869 (7)0.0491 (5)0.045 (2)
C18B0.8956 (7)0.1223 (8)0.0503 (6)0.057 (2)
H18B0.91010.19280.00870.07 (3)*
C19B0.9647 (8)0.0547 (9)0.1126 (7)0.069 (3)
H19B1.02880.07800.11310.07 (3)*
C20B0.9440 (9)0.0428 (10)0.1728 (7)0.072 (3)
H20B0.99350.08800.21530.10 (4)*
C21B0.8536 (10)0.0789 (8)0.1737 (6)0.074 (3)
H21B0.83810.14790.21740.07 (3)*
C22B0.7840 (8)0.0134 (8)0.1099 (6)0.060 (2)
H22B0.72150.03820.10850.07 (3)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br1A0.0604 (6)0.0531 (6)0.0758 (6)0.0167 (5)0.0233 (5)0.0233 (5)
Br2A0.0478 (6)0.0995 (8)0.0736 (7)0.0218 (5)0.0232 (5)0.0087 (6)
S1A0.0660 (15)0.0606 (15)0.0425 (13)0.0205 (13)0.0138 (12)0.0191 (12)
O1A0.075 (4)0.060 (4)0.038 (3)0.021 (3)0.006 (3)0.011 (3)
O2A0.090 (4)0.081 (4)0.067 (4)0.025 (4)0.031 (3)0.034 (3)
N1A0.038 (4)0.051 (4)0.055 (4)0.020 (3)0.014 (3)0.019 (3)
N2A0.043 (4)0.044 (4)0.055 (4)0.020 (3)0.017 (3)0.003 (4)
C1A0.042 (5)0.044 (5)0.059 (5)0.012 (4)0.027 (4)0.014 (4)
C2A0.059 (6)0.064 (6)0.085 (7)0.033 (5)0.019 (5)0.030 (5)
C3A0.045 (6)0.075 (7)0.094 (8)0.035 (5)0.020 (5)0.011 (6)
C4A0.036 (5)0.081 (7)0.086 (7)0.022 (5)0.000 (5)0.023 (6)
C5A0.044 (5)0.048 (5)0.065 (6)0.007 (4)0.011 (5)0.024 (5)
C6A0.042 (5)0.045 (5)0.052 (5)0.016 (4)0.022 (4)0.011 (4)
C7A0.041 (5)0.029 (4)0.047 (5)0.008 (4)0.021 (4)0.010 (4)
C8A0.040 (5)0.049 (5)0.042 (5)0.017 (4)0.022 (4)0.001 (4)
C9A0.043 (5)0.042 (6)0.051 (6)0.013 (4)0.013 (4)0.006 (4)
C10A0.043 (5)0.057 (5)0.039 (5)0.027 (4)0.008 (4)0.014 (4)
C11A0.055 (6)0.072 (6)0.050 (5)0.034 (5)0.008 (5)0.011 (5)
C12A0.099 (9)0.072 (7)0.051 (6)0.053 (7)0.009 (6)0.022 (6)
C13A0.062 (7)0.074 (7)0.072 (7)0.038 (6)0.020 (6)0.046 (6)
C14A0.032 (5)0.076 (7)0.084 (7)0.012 (5)0.007 (5)0.047 (6)
C15A0.036 (5)0.082 (6)0.054 (5)0.028 (5)0.003 (4)0.037 (5)
C16A0.081 (8)0.122 (10)0.126 (11)0.075 (8)0.024 (7)0.054 (11)
C17A0.049 (5)0.063 (6)0.044 (5)0.019 (5)0.000 (4)0.025 (5)
C18A0.061 (7)0.059 (7)0.066 (7)0.019 (6)0.003 (5)0.027 (5)
C19A0.088 (8)0.050 (7)0.070 (7)0.012 (7)0.004 (7)0.019 (6)
C20A0.082 (8)0.057 (7)0.046 (6)0.015 (6)0.018 (6)0.009 (5)
C21A0.073 (7)0.060 (7)0.056 (6)0.023 (6)0.011 (5)0.002 (5)
C22A0.076 (7)0.045 (6)0.054 (6)0.023 (5)0.014 (5)0.005 (5)
Br1B0.0500 (6)0.0833 (7)0.0538 (6)0.0118 (5)0.0042 (4)0.0177 (5)
Br2B0.0720 (7)0.0854 (7)0.0695 (6)0.0262 (6)0.0046 (5)0.0369 (6)
S1B0.0479 (13)0.0561 (14)0.0413 (12)0.0074 (11)0.0052 (10)0.0192 (11)
O1B0.060 (4)0.078 (4)0.075 (4)0.003 (3)0.021 (3)0.049 (3)
O2B0.064 (4)0.079 (4)0.039 (3)0.020 (3)0.002 (3)0.004 (3)
N1B0.043 (4)0.036 (4)0.052 (4)0.008 (3)0.009 (3)0.016 (3)
N2B0.056 (5)0.051 (4)0.069 (5)0.005 (4)0.027 (4)0.026 (4)
C1B0.050 (5)0.027 (5)0.044 (5)0.010 (4)0.012 (4)0.003 (4)
C2B0.054 (6)0.046 (6)0.070 (6)0.017 (5)0.008 (5)0.014 (5)
C3B0.084 (8)0.049 (6)0.107 (9)0.025 (6)0.044 (7)0.004 (6)
C4B0.078 (7)0.039 (6)0.090 (8)0.013 (5)0.039 (6)0.018 (5)
C5B0.083 (7)0.055 (6)0.070 (6)0.003 (6)0.034 (6)0.034 (5)
C6B0.060 (6)0.025 (5)0.056 (5)0.008 (4)0.020 (5)0.010 (4)
C7B0.040 (5)0.034 (5)0.038 (4)0.005 (4)0.006 (4)0.012 (4)
C8B0.045 (5)0.039 (5)0.044 (5)0.016 (4)0.006 (4)0.012 (4)
C9B0.050 (5)0.039 (5)0.063 (6)0.017 (5)0.011 (5)0.012 (4)
C10B0.051 (5)0.040 (5)0.050 (5)0.020 (4)0.012 (5)0.015 (4)
C11B0.051 (6)0.058 (6)0.059 (6)0.021 (5)0.015 (5)0.012 (5)
C12B0.043 (6)0.067 (6)0.078 (7)0.014 (5)0.012 (5)0.020 (5)
C13B0.062 (6)0.062 (6)0.062 (6)0.024 (5)0.022 (5)0.001 (5)
C14B0.072 (7)0.056 (6)0.057 (6)0.030 (5)0.021 (6)0.009 (5)
C15B0.056 (6)0.051 (5)0.055 (6)0.025 (5)0.012 (5)0.018 (4)
C16B0.064 (7)0.099 (9)0.098 (9)0.000 (7)0.041 (6)0.013 (7)
C17B0.044 (5)0.044 (5)0.044 (5)0.009 (4)0.004 (4)0.019 (4)
C18B0.050 (6)0.061 (7)0.067 (6)0.010 (5)0.008 (5)0.040 (6)
C19B0.056 (6)0.075 (8)0.082 (7)0.003 (6)0.024 (6)0.040 (6)
C20B0.071 (7)0.067 (8)0.072 (7)0.004 (6)0.023 (6)0.037 (6)
C21B0.106 (9)0.041 (6)0.057 (6)0.014 (6)0.018 (6)0.003 (5)
C22B0.055 (6)0.052 (6)0.068 (6)0.009 (5)0.005 (5)0.028 (5)
Geometric parameters (Å, º) top
Br1A—C7A1.869 (7)Br1B—C7B1.872 (7)
Br2A—C15A1.884 (8)Br2B—C15B1.911 (8)
S1A—O1A1.416 (5)S1B—O2B1.415 (5)
S1A—O2A1.426 (5)S1B—O1B1.426 (5)
S1A—N1A1.667 (6)S1B—N1B1.668 (6)
S1A—C17A1.728 (8)S1B—C17B1.753 (8)
N1A—C8A1.421 (8)N1B—C1B1.398 (8)
N1A—C1A1.432 (9)N1B—C8B1.442 (9)
N2A—C10A1.391 (8)N2B—C10B1.379 (9)
N2A—C9A1.449 (8)N2B—C9B1.448 (9)
N2A—H2AN0.90N2B—H2BN0.90
C1A—C6A1.380 (9)C1B—C2B1.384 (10)
C1A—C2A1.388 (10)C1B—C6B1.389 (9)
C2A—C3A1.370 (11)C2B—C3B1.414 (11)
C2A—H2A0.96C2B—H2B0.96
C3A—C4A1.378 (11)C3B—C4B1.367 (12)
C3A—H3A0.96C3B—H3B0.96
C4A—C5A1.361 (11)C4B—C5B1.360 (11)
C4A—H4A0.96C4B—H4B0.96
C5A—C6A1.405 (10)C5B—C6B1.411 (10)
C5A—H5A0.96C5B—H5B0.96
C6A—C7A1.426 (9)C6B—C7B1.430 (10)
C7A—C8A1.349 (9)C7B—C8B1.311 (9)
C8A—C9A1.487 (9)C8B—C9B1.496 (9)
C9A—H9A0.96C9B—H9C0.96
C9A—H9B0.96C9B—H9D0.96
C10A—C15A1.382 (10)C10B—C15B1.380 (10)
C10A—C11A1.387 (10)C10B—C11B1.384 (10)
C11A—C12A1.375 (11)C11B—C12B1.383 (10)
C11A—H11A0.96C11B—H11B0.96
C12A—C13A1.374 (12)C12B—C13B1.387 (11)
C12A—H12A0.96C12B—H12B0.96
C13A—C14A1.367 (12)C13B—C14B1.374 (11)
C13A—C16A1.523 (12)C13B—C16B1.505 (11)
C14A—C15A1.389 (10)C14B—C15B1.360 (10)
C14A—H14A0.96C14B—H14B0.96
C16A—H16A0.96C16B—H16D0.96
C16A—H16B0.96C16B—H16E0.96
C16A—H16C0.96C16B—H16F0.96
C17A—C22A1.383 (10)C17B—C18B1.372 (10)
C17A—C18A1.393 (11)C17B—C22B1.377 (10)
C18A—C19A1.359 (12)C18B—C19B1.382 (11)
C18A—H18A0.96C18B—H18B0.96
C19A—C20A1.354 (12)C19B—C20B1.343 (12)
C19A—H19A0.96C19B—H19B0.96
C20A—C21A1.375 (12)C20B—C21B1.370 (12)
C20A—H20A0.96C20B—H20B0.96
C21A—C22A1.385 (11)C21B—C22B1.400 (11)
C21A—H21A0.96C21B—H21B0.96
C22A—H22A0.96C22B—H22B0.96
O1A—S1A—O2A119.9 (3)O2B—S1B—O1B119.7 (3)
O1A—S1A—N1A106.4 (3)O2B—S1B—N1B106.2 (3)
O2A—S1A—N1A105.5 (3)O1B—S1B—N1B106.7 (3)
O1A—S1A—C17A110.0 (4)O2B—S1B—C17B108.2 (4)
O2A—S1A—C17A109.0 (4)O1B—S1B—C17B109.6 (4)
N1A—S1A—C17A104.9 (3)N1B—S1B—C17B105.6 (3)
C8A—N1A—C1A107.0 (6)C1B—N1B—C8B107.6 (6)
C8A—N1A—S1A126.0 (5)C1B—N1B—S1B120.8 (5)
C1A—N1A—S1A121.7 (5)C8B—N1B—S1B127.0 (5)
C10A—N2A—C9A120.6 (6)C10B—N2B—C9B125.2 (7)
C10A—N2A—H2AN119.8C10B—N2B—H2BN117.6
C9A—N2A—H2AN119.6C9B—N2B—H2BN117.2
C6A—C1A—C2A121.4 (8)C2B—C1B—C6B120.4 (7)
C6A—C1A—N1A107.9 (6)C2B—C1B—N1B131.5 (7)
C2A—C1A—N1A130.7 (7)C6B—C1B—N1B108.0 (6)
C3A—C2A—C1A117.4 (8)C1B—C2B—C3B117.4 (8)
C3A—C2A—H2A121.5C1B—C2B—H2B121.5
C1A—C2A—H2A121.1C3B—C2B—H2B121.1
C2A—C3A—C4A122.4 (8)C4B—C3B—C2B122.8 (9)
C2A—C3A—H3A118.8C4B—C3B—H3B118.7
C4A—C3A—H3A118.8C2B—C3B—H3B118.5
C5A—C4A—C3A120.3 (8)C5B—C4B—C3B118.9 (9)
C5A—C4A—H4A120.0C5B—C4B—H4B120.5
C3A—C4A—H4A119.7C3B—C4B—H4B120.6
C4A—C5A—C6A119.0 (8)C4B—C5B—C6B120.6 (9)
C4A—C5A—H5A120.4C4B—C5B—H5B120.0
C6A—C5A—H5A120.5C6B—C5B—H5B119.4
C1A—C6A—C5A119.6 (7)C1B—C6B—C5B119.8 (8)
C1A—C6A—C7A107.2 (7)C1B—C6B—C7B105.9 (6)
C5A—C6A—C7A133.2 (7)C5B—C6B—C7B134.3 (8)
C8A—C7A—C6A109.9 (6)C8B—C7B—C6B111.4 (7)
C8A—C7A—Br1A126.1 (6)C8B—C7B—Br1B126.0 (6)
C6A—C7A—Br1A123.9 (6)C6B—C7B—Br1B122.5 (5)
C7A—C8A—N1A108.0 (6)C7B—C8B—N1B107.0 (6)
C7A—C8A—C9A126.5 (7)C7B—C8B—C9B130.3 (7)
N1A—C8A—C9A125.1 (7)N1B—C8B—C9B122.6 (6)
N2A—C9A—C8A112.0 (6)N2B—C9B—C8B115.4 (6)
N2A—C9A—H9A109.1N2B—C9B—H9C108.5
C8A—C9A—H9A109.3C8B—C9B—H9C108.2
N2A—C9A—H9B109.3N2B—C9B—H9D108.2
C8A—C9A—H9B109.1C8B—C9B—H9D108.8
H9A—C9A—H9B108.0H9C—C9B—H9D107.5
C15A—C10A—C11A116.9 (7)N2B—C10B—C15B120.7 (7)
C15A—C10A—N2A121.8 (7)N2B—C10B—C11B123.9 (7)
C11A—C10A—N2A121.3 (7)C15B—C10B—C11B115.4 (7)
C12A—C11A—C10A121.0 (9)C12B—C11B—C10B121.4 (8)
C12A—C11A—H11A119.3C12B—C11B—H11B119.5
C10A—C11A—H11A119.7C10B—C11B—H11B119.1
C13A—C12A—C11A122.0 (9)C11B—C12B—C13B122.0 (9)
C13A—C12A—H12A118.9C11B—C12B—H12B119.0
C11A—C12A—H12A119.1C13B—C12B—H12B118.9
C14A—C13A—C12A117.5 (8)C14B—C13B—C12B116.2 (8)
C14A—C13A—C16A119.6 (11)C14B—C13B—C16B121.9 (9)
C12A—C13A—C16A122.9 (11)C12B—C13B—C16B121.9 (9)
C13A—C14A—C15A121.2 (8)C15B—C14B—C13B121.4 (8)
C13A—C14A—H14A119.6C15B—C14B—H14B119.3
C15A—C14A—H14A119.2C13B—C14B—H14B119.3
C10A—C15A—C14A121.4 (8)C14B—C15B—C10B123.6 (8)
C10A—C15A—Br2A119.6 (6)C14B—C15B—Br2B117.6 (6)
C14A—C15A—Br2A119.0 (7)C10B—C15B—Br2B118.7 (6)
C13A—C16A—H16A109.4C13B—C16B—H16D110.2
C13A—C16A—H16B109.6C13B—C16B—H16E108.9
H16A—C16A—H16B109.5H16D—C16B—H16E109.5
C13A—C16A—H16C109.4C13B—C16B—H16F109.3
H16A—C16A—H16C109.5H16D—C16B—H16F109.5
H16B—C16A—H16C109.5H16E—C16B—H16F109.5
C22A—C17A—C18A119.1 (8)C18B—C17B—C22B120.2 (8)
C22A—C17A—S1A119.3 (7)C18B—C17B—S1B119.9 (7)
C18A—C17A—S1A121.6 (7)C22B—C17B—S1B119.9 (7)
C19A—C18A—C17A119.0 (10)C17B—C18B—C19B118.8 (9)
C19A—C18A—H18A120.7C17B—C18B—H18B120.6
C17A—C18A—H18A120.2C19B—C18B—H18B120.6
C20A—C19A—C18A122.2 (10)C20B—C19B—C18B121.6 (10)
C20A—C19A—H19A119.0C20B—C19B—H19B119.1
C18A—C19A—H19A118.8C18B—C19B—H19B119.3
C19A—C20A—C21A120.0 (10)C19B—C20B—C21B120.6 (10)
C19A—C20A—H20A120.0C19B—C20B—H20B119.8
C21A—C20A—H20A120.0C21B—C20B—H20B119.6
C20A—C21A—C22A119.0 (10)C20B—C21B—C22B118.9 (9)
C20A—C21A—H21A120.5C20B—C21B—H21B120.5
C22A—C21A—H21A120.4C22B—C21B—H21B120.6
C17A—C22A—C21A120.6 (9)C17B—C22B—C21B119.9 (9)
C17A—C22A—H22A119.5C17B—C22B—H22B120.0
C21A—C22A—H22A119.9C21B—C22B—H22B120.1
O1A—S1A—N1A—C8A34.7 (6)O2B—S1B—N1B—C1B48.2 (6)
O2A—S1A—N1A—C8A163.1 (6)O1B—S1B—N1B—C1B176.9 (5)
C17A—S1A—N1A—C8A81.8 (6)C17B—S1B—N1B—C1B66.6 (6)
O1A—S1A—N1A—C1A174.3 (5)O2B—S1B—N1B—C8B159.1 (6)
O2A—S1A—N1A—C1A46.0 (6)O1B—S1B—N1B—C8B30.4 (7)
C17A—S1A—N1A—C1A69.1 (6)C17B—S1B—N1B—C8B86.1 (7)
C8A—N1A—C1A—C6A0.8 (7)C8B—N1B—C1B—C2B179.5 (7)
S1A—N1A—C1A—C6A156.6 (5)S1B—N1B—C1B—C2B23.1 (11)
C8A—N1A—C1A—C2A179.1 (7)C8B—N1B—C1B—C6B1.5 (8)
S1A—N1A—C1A—C2A23.3 (11)S1B—N1B—C1B—C6B158.9 (5)
C6A—C1A—C2A—C3A0.3 (11)C6B—C1B—C2B—C3B1.1 (11)
N1A—C1A—C2A—C3A179.8 (7)N1B—C1B—C2B—C3B178.9 (7)
C1A—C2A—C3A—C4A0.5 (13)C1B—C2B—C3B—C4B0.7 (13)
C2A—C3A—C4A—C5A0.1 (14)C2B—C3B—C4B—C5B1.0 (14)
C3A—C4A—C5A—C6A1.0 (13)C3B—C4B—C5B—C6B2.4 (13)
C2A—C1A—C6A—C5A1.4 (11)C2B—C1B—C6B—C5B0.2 (11)
N1A—C1A—C6A—C5A178.7 (6)N1B—C1B—C6B—C5B178.0 (6)
C2A—C1A—C6A—C7A179.9 (6)C2B—C1B—C6B—C7B178.9 (6)
N1A—C1A—C6A—C7A0.1 (8)N1B—C1B—C6B—C7B0.6 (8)
C4A—C5A—C6A—C1A1.7 (11)C4B—C5B—C6B—C1B2.0 (12)
C4A—C5A—C6A—C7A179.9 (7)C4B—C5B—C6B—C7B179.8 (8)
C1A—C6A—C7A—C8A0.8 (8)C1B—C6B—C7B—C8B0.6 (9)
C5A—C6A—C7A—C8A179.3 (8)C5B—C6B—C7B—C8B179.0 (8)
C1A—C6A—C7A—Br1A175.9 (5)C1B—C6B—C7B—Br1B176.2 (5)
C5A—C6A—C7A—Br1A2.6 (11)C5B—C6B—C7B—Br1B2.2 (12)
C6A—C7A—C8A—N1A1.3 (8)C6B—C7B—C8B—N1B1.5 (8)
Br1A—C7A—C8A—N1A175.3 (4)Br1B—C7B—C8B—N1B175.1 (5)
C6A—C7A—C8A—C9A174.7 (6)C6B—C7B—C8B—C9B177.8 (7)
Br1A—C7A—C8A—C9A1.9 (10)Br1B—C7B—C8B—C9B1.1 (12)
C1A—N1A—C8A—C7A1.4 (7)C1B—N1B—C8B—C7B1.8 (8)
S1A—N1A—C8A—C7A155.7 (5)S1B—N1B—C8B—C7B157.5 (5)
C1A—N1A—C8A—C9A174.8 (6)C1B—N1B—C8B—C9B178.5 (6)
S1A—N1A—C8A—C9A30.8 (9)S1B—N1B—C8B—C9B25.9 (10)
C10A—N2A—C9A—C8A176.5 (6)C10B—N2B—C9B—C8B83.2 (9)
C7A—C8A—C9A—N2A92.2 (9)C7B—C8B—C9B—N2B115.3 (9)
N1A—C8A—C9A—N2A95.5 (8)N1B—C8B—C9B—N2B60.5 (10)
C9A—N2A—C10A—C15A175.0 (7)C9B—N2B—C10B—C15B167.1 (7)
C9A—N2A—C10A—C11A5.1 (10)C9B—N2B—C10B—C11B14.6 (11)
C15A—C10A—C11A—C12A1.6 (11)N2B—C10B—C11B—C12B179.3 (7)
N2A—C10A—C11A—C12A178.3 (7)C15B—C10B—C11B—C12B1.0 (11)
C10A—C11A—C12A—C13A1.4 (13)C10B—C11B—C12B—C13B1.1 (12)
C11A—C12A—C13A—C14A0.4 (13)C11B—C12B—C13B—C14B0.7 (12)
C11A—C12A—C13A—C16A178.6 (8)C11B—C12B—C13B—C16B180.0 (9)
C12A—C13A—C14A—C15A2.0 (12)C12B—C13B—C14B—C15B0.3 (12)
C16A—C13A—C14A—C15A177.1 (8)C16B—C13B—C14B—C15B179.6 (9)
C11A—C10A—C15A—C14A0.1 (11)C13B—C14B—C15B—C10B0.3 (12)
N2A—C10A—C15A—C14A179.8 (7)C13B—C14B—C15B—Br2B177.8 (6)
C11A—C10A—C15A—Br2A178.2 (5)N2B—C10B—C15B—C14B179.0 (7)
N2A—C10A—C15A—Br2A1.8 (10)C11B—C10B—C15B—C14B0.6 (11)
C13A—C14A—C15A—C10A1.8 (12)N2B—C10B—C15B—Br2B0.9 (9)
C13A—C14A—C15A—Br2A179.9 (6)C11B—C10B—C15B—Br2B177.5 (5)
O1A—S1A—C17A—C22A22.8 (7)O2B—S1B—C17B—C18B14.6 (7)
O2A—S1A—C17A—C22A156.1 (6)O1B—S1B—C17B—C18B146.7 (6)
N1A—S1A—C17A—C22A91.3 (7)N1B—S1B—C17B—C18B98.7 (6)
O1A—S1A—C17A—C18A157.3 (6)O2B—S1B—C17B—C22B164.8 (6)
O2A—S1A—C17A—C18A24.0 (7)O1B—S1B—C17B—C22B32.7 (7)
N1A—S1A—C17A—C18A88.7 (7)N1B—S1B—C17B—C22B81.9 (6)
C22A—C17A—C18A—C19A1.8 (12)C22B—C17B—C18B—C19B0.8 (11)
S1A—C17A—C18A—C19A178.1 (6)S1B—C17B—C18B—C19B178.5 (6)
C17A—C18A—C19A—C20A2.1 (13)C17B—C18B—C19B—C20B1.4 (12)
C18A—C19A—C20A—C21A1.2 (14)C18B—C19B—C20B—C21B0.6 (13)
C19A—C20A—C21A—C22A0.0 (13)C19B—C20B—C21B—C22B0.8 (13)
C18A—C17A—C22A—C21A0.7 (12)C18B—C17B—C22B—C21B0.5 (11)
S1A—C17A—C22A—C21A179.3 (6)S1B—C17B—C22B—C21B179.9 (6)
C20A—C21A—C22A—C17A0.2 (13)C20B—C21B—C22B—C17B1.3 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2A—H2A···O2A0.962.352.956 (11)120
C9A—H9A···O1A0.962.342.894 (10)116
N2A—H2AN···Br2A0.902.643.080 (7)111
C2B—H2B···O2B0.962.362.954 (10)119
C9B—H9D···O1B0.962.482.845 (11)102
N2B—H2BN···Br2B0.902.573.044 (7)114
N2B—H2BN···O1B0.902.322.832 (11)116
C16A—H16C···Br2Bi0.962.883.772 (14)155
C20A—H20A···O2Bii0.962.573.217 (10)125
C5A—H5A···Cg(PS)0.962.783.680 (9)157
C3B—H3B···Cg(PA)ii0.962.893.763 (13)151
Symmetry codes: (i) x1, y, z+1; (ii) x+1, y+1, z.

Experimental details

Crystal data
Chemical formulaC22H18Br2N2O2S
Mr534.26
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)12.436 (3), 12.715 (3), 16.073 (3)
α, β, γ (°)70.13 (3), 69.23 (3), 66.22 (3)
V3)2116.2 (10)
Z4
Radiation typeMo Kα
µ (mm1)3.95
Crystal size (mm)0.40 × 0.30 × 0.30
Data collection
DiffractometerEnraf-Nonius CA-D4
diffractometer
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.301, 0.384
No. of measured, independent and
observed [I > 2σ(I)] reflections
7786, 7411, 3320
Rint0.053
(sin θ/λ)max1)0.594
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.135, 0.95
No. of reflections7411
No. of parameters559
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.63, 0.47

Computer programs: CAD-4 EXPRESS (Enraf-Nonius, 1994), CAD-4 EXPRESS, XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ZORTEP (Zsolnai, 1997), SHELXL97 and PARST (Nardelli, 1995).

Selected geometric parameters (Å, º) top
N1A—C8A1.421 (8)N1B—C1B1.398 (8)
N1A—C1A1.432 (9)N1B—C8B1.442 (9)
N2A—C10A1.391 (8)N2B—C10B1.379 (9)
N2A—C9A1.449 (8)N2B—C9B1.448 (9)
O1A—S1A—O2A119.9 (3)O2B—S1B—O1B119.7 (3)
N1A—S1A—C17A104.9 (3)N1B—S1B—C17B105.6 (3)
O2A—S1A—N1A—C1A46.0 (6)O2B—S1B—N1B—C1B48.2 (6)
C10A—N2A—C9A—C8A176.5 (6)C10B—N2B—C9B—C8B83.2 (9)
N1A—C8A—C9A—N2A95.5 (8)N1B—C8B—C9B—N2B60.5 (10)
O2A—S1A—C17A—C22A156.1 (6)O2B—S1B—C17B—C22B164.8 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2A—H2A···O2A0.962.352.956 (11)120
C9A—H9A···O1A0.962.342.894 (10)116
N2A—H2AN···Br2A0.902.643.080 (7)111
C2B—H2B···O2B0.962.362.954 (10)119
C9B—H9D···O1B0.962.482.845 (11)102
N2B—H2BN···Br2B0.902.573.044 (7)114
N2B—H2BN···O1B0.902.322.832 (11)116
C16A—H16C···Br2Bi0.962.883.772 (14)155
C20A—H20A···O2Bii0.962.573.217 (10)125
C5A—H5A···Cg(PS)0.962.783.680 (9)157
C3B—H3B···Cg(PA)ii0.962.893.763 (13)151
Symmetry codes: (i) x1, y, z+1; (ii) x+1, y+1, z.
 

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