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In the title compound, C24H20Br2N2O4S, the indole ring system is planar and the S atom has a distorted tetrahedral configuration. The sulfonyl-bound phenyl ring is orthogonal to the indole ring system and the conformation of the phenyl­sulfonyl substituent with respect to the indole moiety is influenced by intramolecular C—H...O hydrogen bonds involving the two sulfonyl O atoms. The mean plane through the acetyl­amido group makes a dihedral angle of 57.0 (1)° with the phenyl ring of the benzyl moiety. In the crystal, glide-related mol­ecules are linked together by N—H...O hydrogen bonds and C—H...π interactions to form molecular chains, which extend through the crystal. Inversion-related chains are interlinked by C—H...π interactions to form molecular layers parallel to the bc plane. These layers are interconnected through π–π interactions involving the five- and six-membered rings of the indole moiety.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270103001410/na1592sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270103001410/na1592Isup2.hkl
Contains datablock I

CCDC reference: 208022

Comment top

Indole derivatives have been found to exhibit interesting antibacterial and antifungal properties (Wang & Ng, 2002; Singh et al., 2000; Tsotinis et al., 1997; Quetin-Leclercq et al., 1995). Polyhalogenated indole derivatives exhibit marked antimicrobial activity against Gram-positive and Gram-negative bacteria and fungi (Piscopo, Diurno, Mazzoni, Ciaccio & Veneruso, 1990; Piscopo, Diurno, Mazzoni & Ciaccio, 1990). Pyrido[1,2a]indole derivatives have been identified as potent inhibitors of human immunodeficiency virus type 1 (Taylor et al., 1999) and 5-chloro-3-(phenylsulfonyl)indole-2-carboxamide is reported to be a highly potent non-nucleoside inhibitor of HIV-1 reverse transcriptase (Williams et al., 1993). Indole derivatives also exhibit antitumour activities (Andreani et al., 2001; Bradlow et al., 1999; Cirrincione et al., 1999; Tiwari et al., 1994; Dashwood et al., 1994). Some of the indole alkaloids extracted from plants possess interesting cytotoxic, antitumour or antiparasitic properties (Quetin-Leclercq, 1994; Mukhopadhyay et al., 1981). In view of this wide range of biological activities of indole derivatives, we have undertaken the X-ray structure analysis of the title compound, (I), in order to study its conformation in the solid state. \sch

In compound (I), the indole ring system is planar, with atom C4 deviating by a maximum of 0.022 (4) Å from the weighted least-squares plane through that ring; the dihedral angle formed by the benzene and pyrrole planes is 1.0 (2) Å. The angles at the fused benzene ring of the indole moiety show the same trend as that observed by Benassi et al. (1991) in benzocyclopentanes [average values in square brackets]: C8—C3—C4 120.2 (3) and C3—C8—C7 121.4 (3) [α 120.6 (6)], C3—C4—C5 118.4 (4) and C8—C7—C6 116.5 (4) [β 118.6 (2)], C4—C5—C6 120.9 (4) and C5—C6—C7 122.6 (4) [γ 120.8 (2)], C2—C3—C8 106.6 (3) and N1—C8—C3 107.3 (3) [ε 110.4 (1)], and C2—C3—C4 133.2 (3) and N1—C8—C7 131.3 (3) [δ 128.9 (4)°].

As observed in other related structures (Yokum & Fronczek, 1997; Sankaranarayanan et al., 2000), atom N1 is slightly out of the plane defined by atoms S1, C1 and C8 [deviation 0.141 (2) Å]. The N-Csp2 bond lengths, N1—C1 [1.423 (4) Å] and N1—C8 [1.422 (4) Å], are longer than the mean value reported for N atoms with planar [1.355 (14) Å] and pyramidal [1.416 (18) Å] configurations (Allen et al., 1987). This length increase may be a result of the electron-withdrawing character of the phenylsulfonyl group.

Atom S1 has a distorted tetrahedral configuration, with angles O2—S1—O1 [120.1 (2)°] and N1—S1—C9 [104.5 (1)°] deviating significantly from ideal tetrahedral values. Similar distortions in the sulfonyl group have been reported and are attributed to the repulsive interaction between the short SO bonds (Sankaranarayanan et al., 2001; Seshadri et al., 2002). The conformation of the phenylsulfonyl group with respect to the indole moiety is described by the torsion angles O1—S1—N1—C1 [36.3 (3)°], O2—S1—N1—C8 [−35.2 (3)°] and N1—S1—C9—C10 [116.1 (3)°]. This conformation is influenced by the intramolecular C—H···O hydrogen bonds, C7—H7···O2 and C15—H15A···O1, involving the sulfonyl atoms O1 and O2, which lie almost in the plane of the indole system (Fig. 1 and Table 2). The sulfonyl-bound phenyl ring is orthogonal to the indole ring system, forming a dihedral angle of 89.09 (8)°. The S—N, S—O and S—C distances are comparable with the values reported for related phenylsulfonyl indoles (Sankaranarayanan et al., 2001; Seshadri et al., 2002)

The conformation of the attachment of the benzyl substituent to the indole ring system is described by the N1—C1—C15—C16 torsion angle of 85.9 (3)°; the C1—C15—C16—C17 torsion angle of 38.6 (4)° shows how the phenyl ring of the benzyl moiety is oriented. The mean plane through the acetylamido group makes a dihedral angle of 57.0 (1)° with the benzyl phenyl ring. The low value [10.1 (5)°] of the C20—C19—O3—C22 torsion angle is in agreement with the tendency the methoxy group shows to be coplanar with phenyl, as usually do all the anysoles (Domiano et al., 1979). The sum of the angles around atom N2 is 360°, indicating sp2 hybridization. The N2—C21 bond length of 1.420 (4) Å is closer to the average Car—Nsp3pyramidal value of 1.419 (17) Å than to the Car—Nsp2planar value of 1.353 (7) Å (Allen et al., 1987). This is probably due to some lack of accuracy in the previous data, while the lack of π conjugation of N with phenyl is indicated by the lack of coplanarity of the acetylamido group and the benzyl phenyl ring. The mean planes through the phenyl rings of the benzyl and phenylsulfonyl groups are tilted by 28.7 (1)° and the centroids of these rings are separated by 4.095 (2) Å, indicating the absence of π···π interactions. However, a weak intramolecular C—H···π interaction is observed between these rings, with atoms C10 and H10 separated from the centroid of the benzyl phenyl ring by 3.244 (4) and 2.92 Å, respectively, and the angle subtended at H10 being 102°.

In the crystal of (I), glide-related molecules are linked together by N—H···O hydrogen bonds (Table 2) to form molecular chains, extended through the crystal. The molecular chain structure is further stabilized by C—H···π interactions involving atom C22 and the benzyl phenyl ring of the symmetry-related molecule at (x, 3/2 − y, z − 1/2). Neighbouring inversion-related chains are interlinked by C—H···π interactions involving atom C12 and benzene ring of the indole moiety at (-x, 1 − y, −z), to form layers parallel to the bc plane (Fig. 2). This interaction results in the formation of centrosymmetrically C—H···π-bonded dimeric pairs. The geometry of the C—H···π interaction is given in Table 2, in which Cg1 and Cg2 denote the centroids of the rings C3—C8 and C16—C21, respectively. Since the sulfonyl phenyl ring is orthogonal to the indole moiety, the benzene ring of the indole moiety and the symmetry-related phenyl rings are arranged to form a T-shaped structure, with their centroids separated by 5.123 (2) Å. This distance is slightly larger than the separation of 5.10 Å reported for normal T-shaped π···π stacking interactions (Hobza et al., 1994). These dimeric pairs are packed along the cell diagonal such that the indole moieties of the (1 − x, 1 − y, 1 − z) adjacent pairs face each other, with the centroids of the five- and six-membered rings separated by 3.769 (2) Å, an indication for π···π interactions (Fig. 3). In addition to these interactions, a short intermolecular contact of 3.247 (4) Å is observed between atom Br1 and atom C13 of the molecule translated one unit along the c axis.

Experimental top

To a solution of 3-bromo-1-phenylsulfonylindol-2-ylmethanol (3.6 g, 10 mmol) in chloroform (200 ml), a solution of 4-bromo-3-methoxyactanilide (2.34 g, 10 mmol) in the same solvent (25 ml) was added, followed by anhydrous magnesium sulfate (10 g) and boron trifluoride etherate (2.0 ml). The resulting solution was refluxed for 3 h. Water (100 ml) was then added, and the organic layer was separated and washed with 20% hydrochloric acid (1 × 50 ml), followed by water and saturated bicarbonate solution. The solvent was removed by distillation after drying over anhydrous sodium sulfate. The residue was chromatographed on a silica gel column (350 mesh) and eluted successively with 20% ethyl acetate in hexane, followed by 25% and then finally with 30%. The 30% ethyl acetate in hexane eluent gave 2-arylmethylindole, which was then crystallized from hexane-chloroform (2:1) to give crystals of (I) (m.p. 455–457 K).

Refinement top

The H atoms were fixed geometrically and allowed to ride on the corresponding non-H atoms, with an N—H distance of 0.86 Å and C—H distances in the range 0.93–0.96 Å. The isotropic displacement parameters were set equal to 1.5Ueq(C) for methyl H atoms and 1.2Ueq(C) for all others. Rotating group refinement was used for the methyl groups.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2002).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing the intramolecular interactions. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.
[Figure 2] Fig. 2. A view of the molecular network of (I) down the a axis. For clarity, only the H atoms involved in the hydrogen bonds are shown.
[Figure 3] Fig. 3. A view of the C—H···π hydrogen-bonded dimers and π···π interactions in (I).
N-{4-Bromo-2-[(3-bromo-1-phenylsulfonyl-1H-indol-2-yl)methyl]- 5-methoxyphenyl}acetamide top
Crystal data top
C24H20Br2N2O4SF(000) = 1184
Mr = 592.30Dx = 1.620 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4221 reflections
a = 10.2647 (11) Åθ = 2.3–25.0°
b = 24.976 (3) ŵ = 3.46 mm1
c = 9.7963 (11) ÅT = 293 K
β = 104.760 (2)°Block, colourless
V = 2428.6 (5) Å30.34 × 0.30 × 0.24 mm
Z = 4
Data collection top
Siemens SMART CCD area-detector
diffractometer
5984 independent reflections
Radiation source: fine-focus sealed tube3727 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
Detector resolution: 8.33 pixels mm-1θmax = 28.3°, θmin = 2.3°
ω scansh = 1311
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 3317
Tmin = 0.343, Tmax = 0.436l = 1211
15276 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.097 w = 1/[σ2(Fo2) + (0.0316P)2 + 2.342P]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.001
5984 reflectionsΔρmax = 0.85 e Å3
301 parametersΔρmin = 0.74 e Å3
0 restraintsExtinction correction: SHELXTL (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0023 (3)
Crystal data top
C24H20Br2N2O4SV = 2428.6 (5) Å3
Mr = 592.30Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.2647 (11) ŵ = 3.46 mm1
b = 24.976 (3) ÅT = 293 K
c = 9.7963 (11) Å0.34 × 0.30 × 0.24 mm
β = 104.760 (2)°
Data collection top
Siemens SMART CCD area-detector
diffractometer
5984 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
3727 reflections with I > 2σ(I)
Tmin = 0.343, Tmax = 0.436Rint = 0.031
15276 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.097H-atom parameters constrained
S = 1.00Δρmax = 0.85 e Å3
5984 reflectionsΔρmin = 0.74 e Å3
301 parameters
Special details top

Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different ϕ angle (0, 88 and 180°) for the crystal and each exposure of 10 s covered 0.3° in ω. The crystal-to-detector distance was 5 cm and the detector swing angle was −35°. Crystal decay was monitored by repeating 50 initial frames at the end of data collection and analysing the intensity of duplicate reflections, and was found to be negligible.

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
Br10.20399 (5)0.525447 (19)0.61987 (4)0.07004 (16)
Br20.20760 (3)0.621306 (16)0.15807 (5)0.06130 (15)
S10.40916 (8)0.57943 (3)0.16260 (8)0.0389 (2)
O10.4415 (2)0.63271 (9)0.2115 (2)0.0526 (6)
O20.5023 (2)0.54912 (11)0.1093 (3)0.0578 (7)
O30.1301 (2)0.73029 (10)0.0752 (3)0.0604 (7)
O40.3592 (2)0.72820 (9)0.5837 (2)0.0497 (6)
N10.3829 (2)0.54460 (10)0.2993 (2)0.0346 (6)
N20.3329 (2)0.73313 (10)0.3483 (3)0.0354 (6)
H2N0.36790.74450.28270.042*
C10.3208 (3)0.56454 (12)0.4033 (3)0.0307 (6)
C20.2842 (3)0.52187 (13)0.4687 (3)0.0384 (7)
C30.3200 (3)0.47336 (13)0.4120 (3)0.0407 (8)
C40.3070 (4)0.41946 (15)0.4442 (4)0.0571 (10)
H40.26890.40960.51700.069*
C50.3514 (4)0.38179 (17)0.3664 (5)0.0708 (13)
H50.34260.34570.38570.085*
C60.4095 (4)0.39641 (17)0.2593 (5)0.0724 (13)
H60.43850.36960.20800.087*
C70.4261 (4)0.44930 (15)0.2253 (4)0.0579 (10)
H70.46600.45860.15340.069*
C80.3801 (3)0.48770 (13)0.3041 (3)0.0406 (8)
C90.2518 (3)0.57966 (14)0.0381 (3)0.0398 (7)
C100.1868 (4)0.62804 (17)0.0019 (4)0.0652 (11)
H100.22610.66000.04050.078*
C110.0608 (5)0.6275 (2)0.0940 (5)0.0909 (17)
H110.01520.65950.12110.109*
C120.0037 (4)0.5800 (3)0.1487 (4)0.0887 (17)
H120.08180.58010.21040.106*
C130.0697 (4)0.5330 (2)0.1144 (4)0.0711 (13)
H130.03020.50120.15370.085*
C140.1966 (4)0.53231 (16)0.0206 (4)0.0541 (9)
H140.24330.50030.00210.065*
C150.3125 (3)0.62219 (12)0.4397 (3)0.0343 (7)
H15A0.39510.63970.43310.041*
H15B0.30820.62460.53730.041*
C160.1946 (3)0.65302 (12)0.3494 (3)0.0317 (6)
C170.0678 (3)0.62949 (12)0.3038 (3)0.0359 (7)
H170.05450.59510.33400.043*
C180.0383 (3)0.65597 (13)0.2152 (3)0.0375 (7)
C190.0219 (3)0.70722 (13)0.1671 (3)0.0403 (8)
C200.1018 (3)0.73212 (13)0.2160 (3)0.0390 (7)
H200.11380.76690.18780.047*
C210.2082 (3)0.70546 (12)0.3070 (3)0.0324 (7)
C220.1075 (4)0.77914 (17)0.0098 (5)0.0755 (13)
H22A0.18810.78920.05960.113*
H22B0.03540.77440.03520.113*
H22C0.08390.80670.07990.113*
C230.4004 (3)0.74286 (12)0.4833 (3)0.0370 (7)
C240.5303 (3)0.77309 (15)0.5012 (4)0.0556 (9)
H24A0.59870.75700.57530.083*
H24B0.51750.80960.52520.083*
H24C0.55770.77200.41460.083*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0761 (3)0.0823 (3)0.0614 (3)0.0004 (2)0.0353 (2)0.0172 (2)
Br20.02974 (17)0.0598 (3)0.0847 (3)0.00649 (17)0.00305 (17)0.0132 (2)
S10.0360 (4)0.0478 (5)0.0344 (4)0.0036 (4)0.0116 (3)0.0020 (4)
O10.0622 (15)0.0485 (15)0.0496 (14)0.0176 (12)0.0188 (12)0.0005 (12)
O20.0439 (14)0.0796 (18)0.0549 (15)0.0058 (13)0.0219 (12)0.0100 (13)
O30.0345 (12)0.0635 (17)0.0766 (18)0.0074 (12)0.0023 (12)0.0328 (14)
O40.0588 (15)0.0541 (15)0.0391 (13)0.0126 (12)0.0177 (11)0.0125 (11)
N10.0363 (13)0.0363 (14)0.0290 (13)0.0035 (11)0.0044 (11)0.0006 (11)
N20.0324 (13)0.0374 (15)0.0372 (14)0.0059 (11)0.0105 (11)0.0001 (12)
C10.0261 (14)0.0364 (17)0.0253 (15)0.0026 (12)0.0013 (11)0.0017 (13)
C20.0346 (16)0.0448 (19)0.0337 (16)0.0025 (14)0.0050 (13)0.0059 (15)
C30.0327 (16)0.0376 (18)0.0420 (18)0.0008 (14)0.0084 (14)0.0063 (15)
C40.051 (2)0.044 (2)0.064 (2)0.0009 (18)0.0085 (18)0.011 (2)
C50.069 (3)0.040 (2)0.082 (3)0.003 (2)0.019 (2)0.006 (2)
C60.076 (3)0.045 (2)0.078 (3)0.022 (2)0.013 (2)0.020 (2)
C70.066 (2)0.048 (2)0.052 (2)0.0157 (19)0.0007 (18)0.0097 (18)
C80.0373 (17)0.0349 (18)0.0397 (18)0.0058 (14)0.0085 (14)0.0018 (15)
C90.0404 (17)0.055 (2)0.0252 (15)0.0003 (16)0.0110 (13)0.0020 (15)
C100.082 (3)0.069 (3)0.039 (2)0.019 (2)0.0054 (19)0.0001 (19)
C110.092 (4)0.123 (5)0.046 (3)0.059 (3)0.004 (2)0.002 (3)
C120.049 (2)0.166 (6)0.043 (2)0.015 (3)0.0027 (19)0.003 (3)
C130.061 (3)0.107 (4)0.041 (2)0.025 (3)0.0041 (19)0.001 (2)
C140.056 (2)0.063 (2)0.0386 (19)0.0117 (19)0.0034 (16)0.0074 (18)
C150.0308 (14)0.0377 (17)0.0309 (16)0.0024 (14)0.0018 (12)0.0034 (14)
C160.0319 (15)0.0331 (16)0.0297 (15)0.0028 (13)0.0070 (12)0.0022 (13)
C170.0315 (15)0.0328 (17)0.0428 (18)0.0005 (13)0.0082 (13)0.0053 (14)
C180.0235 (14)0.0412 (18)0.0457 (19)0.0001 (13)0.0050 (13)0.0017 (15)
C190.0284 (15)0.045 (2)0.0467 (19)0.0068 (14)0.0077 (14)0.0108 (15)
C200.0370 (17)0.0348 (17)0.0451 (19)0.0025 (14)0.0105 (14)0.0066 (14)
C210.0290 (14)0.0376 (17)0.0324 (16)0.0018 (13)0.0109 (12)0.0010 (13)
C220.057 (2)0.078 (3)0.088 (3)0.017 (2)0.011 (2)0.046 (3)
C230.0332 (16)0.0289 (16)0.049 (2)0.0003 (13)0.0098 (15)0.0084 (15)
C240.0418 (19)0.051 (2)0.070 (2)0.0121 (17)0.0083 (18)0.0100 (19)
Geometric parameters (Å, º) top
Br1—C21.871 (3)C9—C101.382 (5)
Br2—C181.894 (3)C10—C111.392 (6)
S1—O21.419 (2)C10—H100.93
S1—O11.425 (2)C11—C121.370 (7)
S1—N11.675 (3)C11—H110.93
S1—C91.759 (3)C12—C131.355 (7)
O3—C191.366 (4)C12—H120.93
O3—C221.424 (4)C13—C141.389 (5)
O4—C231.221 (4)C13—H130.93
N1—C81.422 (4)C14—H140.93
N1—C11.423 (4)C15—C161.515 (4)
N2—C231.350 (4)C15—H15A0.97
N2—C211.420 (4)C15—H15B0.97
N2—H2N0.86C16—C211.392 (4)
C1—C21.345 (4)C16—C171.394 (4)
C1—C151.491 (4)C17—C181.376 (4)
C2—C31.420 (4)C17—H170.93
C3—C41.397 (5)C18—C191.389 (4)
C3—C81.399 (5)C19—C201.385 (4)
C4—C51.360 (6)C20—C211.391 (4)
C4—H40.93C20—H200.93
C5—C61.382 (7)C22—H22A0.96
C5—H50.93C22—H22B0.96
C6—C71.384 (6)C22—H22C0.96
C6—H60.93C23—C241.503 (4)
C7—C81.387 (5)C24—H24A0.96
C7—H70.93C24—H24B0.96
C9—C141.373 (5)C24—H24C0.96
O2—S1—O1120.06 (15)C13—C12—H12119.5
O2—S1—N1106.12 (15)C11—C12—H12119.5
O1—S1—N1106.70 (13)C12—C13—C14120.0 (4)
O2—S1—C9109.40 (15)C12—C13—H13120.0
O1—S1—C9108.91 (16)C14—C13—H13120.0
N1—S1—C9104.48 (14)C9—C14—C13119.0 (4)
C19—O3—C22117.4 (3)C9—C14—H14120.5
C8—N1—C1108.0 (2)C13—C14—H14120.5
C8—N1—S1123.7 (2)C1—C15—C16115.9 (2)
C1—N1—S1125.7 (2)C1—C15—H15A108.3
C23—N2—C21124.6 (3)C16—C15—H15A108.3
C23—N2—H2N117.7C1—C15—H15B108.3
C21—N2—H2N117.7C16—C15—H15B108.3
C2—C1—N1107.1 (3)H15A—C15—H15B107.4
C2—C1—C15127.7 (3)C21—C16—C17117.2 (3)
N1—C1—C15124.9 (3)C21—C16—C15121.8 (3)
C1—C2—C3111.0 (3)C17—C16—C15121.0 (3)
C1—C2—Br1124.9 (2)C18—C17—C16121.6 (3)
C3—C2—Br1124.1 (2)C18—C17—H17119.2
C4—C3—C8120.2 (3)C16—C17—H17119.2
C4—C3—C2133.2 (3)C17—C18—C19120.8 (3)
C8—C3—C2106.6 (3)C17—C18—Br2119.0 (2)
C5—C4—C3118.4 (4)C19—C18—Br2120.2 (2)
C5—C4—H4120.8O3—C19—C20123.9 (3)
C3—C4—H4120.8O3—C19—C18117.6 (3)
C4—C5—C6120.9 (4)C20—C19—C18118.4 (3)
C4—C5—H5119.6C19—C20—C21120.5 (3)
C6—C5—H5119.6C19—C20—H20119.7
C5—C6—C7122.6 (4)C21—C20—H20119.7
C5—C6—H6118.7C20—C21—C16121.3 (3)
C7—C6—H6118.7C20—C21—N2117.0 (3)
C6—C7—C8116.5 (4)C16—C21—N2121.6 (3)
C6—C7—H7121.8O3—C22—H22A109.5
C8—C7—H7121.8O3—C22—H22B109.5
C7—C8—C3121.4 (3)H22A—C22—H22B109.5
C7—C8—N1131.3 (3)O3—C22—H22C109.5
C3—C8—N1107.3 (3)H22A—C22—H22C109.5
C14—C9—C10121.6 (3)H22B—C22—H22C109.5
C14—C9—S1119.7 (3)O4—C23—N2122.5 (3)
C10—C9—S1118.6 (3)O4—C23—C24122.4 (3)
C9—C10—C11118.0 (4)N2—C23—C24115.0 (3)
C9—C10—H10121.0C23—C24—H24A109.5
C11—C10—H10121.0C23—C24—H24B109.5
C12—C11—C10120.2 (5)H24A—C24—H24B109.5
C12—C11—H11119.9C23—C24—H24C109.5
C10—C11—H11119.9H24A—C24—H24C109.5
C13—C12—C11121.1 (4)H24B—C24—H24C109.5
O2—S1—N1—C835.2 (3)O1—S1—C9—C102.4 (3)
O1—S1—N1—C8164.4 (2)N1—S1—C9—C10116.1 (3)
C9—S1—N1—C880.3 (3)C14—C9—C10—C111.6 (6)
O2—S1—N1—C1165.4 (2)S1—C9—C10—C11178.4 (3)
O1—S1—N1—C136.3 (3)C9—C10—C11—C120.7 (7)
C9—S1—N1—C179.0 (3)C10—C11—C12—C132.1 (7)
C8—N1—C1—C20.8 (3)C11—C12—C13—C141.1 (7)
S1—N1—C1—C2162.8 (2)C10—C9—C14—C132.6 (5)
C8—N1—C1—C15175.2 (2)S1—C9—C14—C13177.4 (3)
S1—N1—C1—C1522.8 (4)C12—C13—C14—C91.2 (6)
N1—C1—C2—C30.1 (3)C2—C1—C15—C16101.0 (4)
C15—C1—C2—C3174.0 (3)N1—C1—C15—C1685.9 (3)
N1—C1—C2—Br1177.4 (2)C1—C15—C16—C21140.6 (3)
C15—C1—C2—Br13.3 (4)C1—C15—C16—C1738.6 (4)
C1—C2—C3—C4178.5 (3)C21—C16—C17—C183.0 (4)
Br1—C2—C3—C41.2 (5)C15—C16—C17—C18176.3 (3)
C1—C2—C3—C81.0 (3)C16—C17—C18—C190.5 (5)
Br1—C2—C3—C8178.3 (2)C16—C17—C18—Br2180.0 (2)
C8—C3—C4—C51.3 (5)C22—O3—C19—C2010.1 (5)
C2—C3—C4—C5179.2 (3)C22—O3—C19—C18170.7 (3)
C3—C4—C5—C60.7 (6)C17—C18—C19—O3177.6 (3)
C4—C5—C6—C70.2 (6)Br2—C18—C19—O32.0 (4)
C5—C6—C7—C80.5 (6)C17—C18—C19—C203.2 (5)
C6—C7—C8—C30.1 (5)Br2—C18—C19—C20177.3 (2)
C6—C7—C8—N1178.9 (3)O3—C19—C20—C21178.5 (3)
C4—C3—C8—C71.0 (5)C18—C19—C20—C212.4 (5)
C2—C3—C8—C7179.4 (3)C19—C20—C21—C161.2 (5)
C4—C3—C8—N1178.2 (3)C19—C20—C21—N2177.9 (3)
C2—C3—C8—N11.5 (3)C17—C16—C21—C203.8 (4)
C1—N1—C8—C7179.5 (3)C15—C16—C21—C20175.5 (3)
S1—N1—C8—C717.1 (5)C17—C16—C21—N2179.6 (3)
C1—N1—C8—C31.4 (3)C15—C16—C21—N21.1 (4)
S1—N1—C8—C3163.9 (2)C23—N2—C21—C20123.7 (3)
O2—S1—C9—C1449.4 (3)C23—N2—C21—C1659.5 (4)
O1—S1—C9—C14177.6 (3)C21—N2—C23—O40.2 (5)
N1—S1—C9—C1463.9 (3)C21—N2—C23—C24179.8 (3)
O2—S1—C9—C10130.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7···O20.932.352.928 (5)120
C10—H10···O10.932.502.886 (5)105
C15—H15A···O10.972.342.886 (4)115
C15—H15A···N20.972.502.936 (4)107
C15—H15B···Br10.972.893.346 (3)110
N2—H2N···O4i0.862.052.843 (3)154
C10—H10···Cg20.932.923.244 (5)102
C22—H22B···Cg2i0.962.853.661 (6)143
C12—H12···Cg1ii0.932.883.784 (5)164
Symmetry codes: (i) x, y+3/2, z1/2; (ii) x, y+1, z.

Experimental details

Crystal data
Chemical formulaC24H20Br2N2O4S
Mr592.30
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)10.2647 (11), 24.976 (3), 9.7963 (11)
β (°) 104.760 (2)
V3)2428.6 (5)
Z4
Radiation typeMo Kα
µ (mm1)3.46
Crystal size (mm)0.34 × 0.30 × 0.24
Data collection
DiffractometerSiemens SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.343, 0.436
No. of measured, independent and
observed [I > 2σ(I)] reflections
15276, 5984, 3727
Rint0.031
(sin θ/λ)max1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.097, 1.00
No. of reflections5984
No. of parameters301
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.85, 0.74

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXTL (Sheldrick, 1997), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2002).

Selected geometric parameters (Å, º) top
S1—O21.419 (2)N1—C81.422 (4)
S1—O11.425 (2)N1—C11.423 (4)
S1—N11.675 (3)N2—C231.350 (4)
S1—C91.759 (3)N2—C211.420 (4)
O4—C231.221 (4)
O2—S1—O1120.06 (15)N1—S1—C9104.48 (14)
O2—S1—N1106.12 (15)C5—C6—C7122.6 (4)
O1—S1—N1106.70 (13)C6—C7—C8116.5 (4)
O2—S1—C9109.40 (15)C1—C15—C16115.9 (2)
O1—S1—C9108.91 (16)
O2—S1—N1—C835.2 (3)O2—S1—C9—C10130.6 (3)
O1—S1—N1—C8164.4 (2)O1—S1—C9—C102.4 (3)
O2—S1—N1—C1165.4 (2)N1—C1—C15—C1685.9 (3)
O1—S1—N1—C136.3 (3)C1—C15—C16—C1738.6 (4)
O2—S1—C9—C1449.4 (3)C22—O3—C19—C2010.1 (5)
O1—S1—C9—C14177.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7···O20.932.352.928 (5)120
C10—H10···O10.932.502.886 (5)105
C15—H15A···O10.972.342.886 (4)115
C15—H15A···N20.972.502.936 (4)107
C15—H15B···Br10.972.893.346 (3)110
N2—H2N···O4i0.862.052.843 (3)154
C10—H10···Cg20.932.923.244 (5)102
C22—H22B···Cg2i0.962.853.661 (6)143
C12—H12···Cg1ii0.932.883.784 (5)164
Symmetry codes: (i) x, y+3/2, z1/2; (ii) x, y+1, z.
 

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