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Acta Cryst. (2007). E63, o3854
https://doi.org/10.1107/S1600536807037932
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4,4′,6,6′-Tetra­bromo-2,2′-[dithio­bis(o-phenyl­enenitrilo­methyl­idyne)]diphenol

L.-X. Jin, Z. Liu, J.-H. Xia and G.-Z. Li
The title Schiff base, C26H16Br4N2O2S2, was synthesized from 3,5-dibromo­salicylaldehyde and 2-amino­benzene­thiol. C—H...Br hydrogen bonds link the mol­ecules into a one-dimensional chain which resembles a staircase. The chains are further joined to form a three-dimensional supra­molecular network via C—H...Br hydrogen bonds and S...Br inter­actions.
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Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807037932/at2337sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807037932/at2337Isup2.hkl
Contains datablock I

CCDC reference: 660321

checkCIF report

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](Wave) = 0.000 Å
  • R factor = 0.048
  • wR factor = 0.103
  • Data-to-parameter ratio = 14.5

checkCIF/PLATON results

No syntax errors found




Alert level G
ABSTM02_ALERT_3_G  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      0.935
            Tmax scaled      0.540 Tmin scaled      0.259


   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   0 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check
Comment top

Schiff bases, the organic ligands, have recently been focused by the coordination chemists as versatile spacers because of their preparative accessibilities, structural varieties and varied denticities (Rahaman et al., 2005). The potential biological activity of compounds containing sulfur and nitrogen may be better than other compounds, such as antitumor, antibacterial and et al. (Zhong et al., 2006; Ravoof et al., 2007; Lv et al., 2006), and applies of Schiff base in analysis are very comprehensive today. So we report herein the ligand 3,5-dibromosalicylaldehyde (2-aminobenzenethiol), (I).

One molecule is composed by two Schiff bases which are boned by S1—S2 (Elmali et al., 1995). Two Schiff bases are not in one face, and distances between O, N, S are not far away, so it is conferred that two metal atoms can be coordinated at least (Fig.1). As shown in Fig. 2 and Fig. 3, weak C—H···Br hydrogen bonds and S···Br are also found in this ligand. The C—H···Br hydrogen bonds line the molecules like a chain (Fig. 2). The S···Br weak interaction connected each adjacent ligand to form a two-dimensional network structure (Fig. 3). Both supramolecular role contribute to the stability of the structure (Taylor et al., 1984).

This new Schiff base (I) is a new analysis reagent, put forward the spectrophotometric determination of copperII. The new reagent gives yellow coloured water solution with copperII at room temperature. The complex shows an absorbance maximum at 400 nm. and a higher absorption peak if more copperII was added. So an analysis method can be established.

Related literature top

One molecule is composed of two Schiff bases which are bonded by S1—S2 (Elmali et al., 1995). For related literature, see: Ghosh & Bharadwaj (2004); Ghosh et al. (2005); Lv et al. (2006); Raghuraman et al. (2003); Rahaman et al. (2005); Ravoof et al. (2007); Taylor & Kennard (1984); Zhong et al. (2006).

Experimental top

The schiff base was prepared as follows: a solution of 3,5-dibromosalicyaldehyde in ethanol was put in a flask. To this solution, 2-aminobenzenethiol in ethanol was added slowly. After stirring at 323 K for 1 h, the title compound (I) was obtained as Red–brown crystalline solid by slow evaporation of ethanol from the reaction mixture at room temperature.

Refinement top

All H atoms were positioned geometrically and refined as riding on their carrier C and O atoms, with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C) and O—H = 0.82 Å and Uiso(H) = 1.5Ueq(O).

Structure description top

Schiff bases, the organic ligands, have recently been focused by the coordination chemists as versatile spacers because of their preparative accessibilities, structural varieties and varied denticities (Rahaman et al., 2005). The potential biological activity of compounds containing sulfur and nitrogen may be better than other compounds, such as antitumor, antibacterial and et al. (Zhong et al., 2006; Ravoof et al., 2007; Lv et al., 2006), and applies of Schiff base in analysis are very comprehensive today. So we report herein the ligand 3,5-dibromosalicylaldehyde (2-aminobenzenethiol), (I).

One molecule is composed by two Schiff bases which are boned by S1—S2 (Elmali et al., 1995). Two Schiff bases are not in one face, and distances between O, N, S are not far away, so it is conferred that two metal atoms can be coordinated at least (Fig.1). As shown in Fig. 2 and Fig. 3, weak C—H···Br hydrogen bonds and S···Br are also found in this ligand. The C—H···Br hydrogen bonds line the molecules like a chain (Fig. 2). The S···Br weak interaction connected each adjacent ligand to form a two-dimensional network structure (Fig. 3). Both supramolecular role contribute to the stability of the structure (Taylor et al., 1984).

This new Schiff base (I) is a new analysis reagent, put forward the spectrophotometric determination of copperII. The new reagent gives yellow coloured water solution with copperII at room temperature. The complex shows an absorbance maximum at 400 nm. and a higher absorption peak if more copperII was added. So an analysis method can be established.

One molecule is composed of two Schiff bases which are bonded by S1—S2 (Elmali et al., 1995). For related literature, see: Ghosh & Bharadwaj (2004); Ghosh et al. (2005); Lv et al. (2006); Raghuraman et al. (2003); Rahaman et al. (2005); Ravoof et al. (2007); Taylor & Kennard (1984); Zhong et al. (2006).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure of the ligand (I), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. one-dimensional chain structure of the ligand (I).
[Figure 3] Fig. 3. two-dimensional layer structure of the ligand (I).
4,4',6,6'-Tetrabromo-2,2'-[dithiobis(o-phenylenenitrilomethylidyne)]diphenol top
Crystal data top
C26H16Br4N2O2S2V = 1346.9 (4) Å3
Mr = 772.17Z = 2
Triclinic, P1F(000) = 748
Hall symbol: -P 1Dx = 1.904 Mg m−3
a = 10.4361 (17) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.4199 (18) ŵ = 6.16 mm−1
c = 12.938 (2) ÅT = 298 K
α = 89.721 (3)°Block, red
β = 71.536 (2)°0.28 × 0.16 × 0.10 mm
γ = 68.211 (2)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		4705 independent reflections
Radiation source: fine-focus sealed tube2583 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
φ and ω scansθmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −12→12
Tmin = 0.277, Tmax = 0.578k = −12→13
7083 measured reflectionsl = −12→15
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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0364P)2]
where P = (Fo2 + 2Fc2)/3
4705 reflections(Δ/σ)max = 0.001
325 parametersΔρmax = 0.67 e Å−3
0 restraintsΔρmin = −0.52 e Å−3
Crystal data top
C26H16Br4N2O2S2γ = 68.211 (2)°
Mr = 772.17V = 1346.9 (4) Å3
Triclinic, P1Z = 2
a = 10.4361 (17) ÅMo Kα radiation
b = 11.4199 (18) ŵ = 6.16 mm−1
c = 12.938 (2) ÅT = 298 K
α = 89.721 (3)°0.28 × 0.16 × 0.10 mm
β = 71.536 (2)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		4705 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2583 reflections with I > 2σ(I)
Tmin = 0.277, Tmax = 0.578Rint = 0.034
7083 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.103H-atom parameters constrained
S = 1.00Δρmax = 0.67 e Å−3
4705 reflectionsΔρmin = −0.52 e Å−3
325 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
Br10.93027 (8)0.39861 (7)0.41754 (6)0.0631 (3)
Br21.44706 (8)−0.03777 (8)0.21997 (6)0.0723 (3)
Br30.86654 (8)0.71957 (8)1.26383 (6)0.0698 (3)
Br40.43115 (9)0.78697 (8)1.67614 (6)0.0690 (3)
N10.9772 (5)0.0487 (5)0.7093 (4)0.0394 (13)
N20.4884 (5)0.5127 (5)1.2167 (4)0.0421 (13)
O10.8957 (4)0.2397 (4)0.6008 (3)0.0470 (11)
H10.88770.19620.65120.071*
O20.6965 (5)0.5945 (5)1.1942 (4)0.0650 (14)
H20.64940.56041.17520.098*
S10.79827 (19)0.24089 (17)0.88492 (13)0.0501 (5)
S20.70339 (18)0.33660 (18)1.03865 (14)0.0532 (5)
C11.0880 (7)−0.0061 (6)0.6243 (5)0.0430 (17)
H1A1.1525−0.08800.62510.052*
C21.1179 (6)0.0547 (6)0.5251 (5)0.0374 (16)
C31.0214 (7)0.1775 (6)0.5193 (5)0.0382 (16)
C41.0596 (7)0.2332 (6)0.4252 (5)0.0422 (16)
C51.1858 (7)0.1714 (6)0.3370 (5)0.0446 (17)
H51.20810.21080.27450.054*
C61.2785 (7)0.0504 (7)0.3425 (5)0.0480 (18)
C71.2461 (7)−0.0082 (6)0.4356 (5)0.0423 (16)
H71.3097−0.08960.43880.051*
C80.9465 (6)−0.0068 (6)0.8074 (5)0.0369 (15)
C90.8537 (7)0.0765 (6)0.9017 (5)0.0420 (17)
C100.8122 (7)0.0326 (7)1.0005 (5)0.0555 (19)
H100.74910.08921.06350.067*
C110.8654 (8)−0.0968 (8)1.0051 (7)0.064 (2)
H110.8363−0.12771.07140.077*
C120.9606 (8)−0.1799 (7)0.9129 (7)0.059 (2)
H120.9987−0.26660.91760.071*
C131.0006 (7)−0.1362 (7)0.8129 (6)0.0528 (19)
H131.0632−0.19300.75000.063*
C140.4397 (7)0.5530 (6)1.3193 (5)0.0420 (16)
H140.35780.54071.36460.050*
C150.5082 (7)0.6176 (6)1.3676 (5)0.0397 (16)
C160.6351 (7)0.6344 (6)1.3020 (5)0.0448 (17)
C170.6972 (7)0.6964 (6)1.3508 (6)0.0496 (18)
C180.6378 (7)0.7390 (6)1.4610 (6)0.0485 (18)
H180.68190.77891.49260.058*
C190.5134 (7)0.7235 (6)1.5254 (5)0.0452 (17)
C200.4499 (7)0.6628 (6)1.4787 (5)0.0407 (16)
H200.36630.65171.52230.049*
C210.4218 (7)0.4508 (6)1.1691 (5)0.0355 (15)
C220.5164 (6)0.3641 (6)1.0753 (5)0.0379 (16)
C230.4613 (7)0.3024 (7)1.0211 (5)0.0533 (19)
H230.52380.24310.95960.064*
C240.3122 (8)0.3284 (7)1.0579 (6)0.060 (2)
H240.27520.28691.02050.072*
C250.2190 (7)0.4150 (7)1.1490 (6)0.0525 (19)
H250.11900.43251.17270.063*
C260.2731 (7)0.4755 (6)1.2052 (5)0.0462 (17)
H260.21000.53321.26760.055*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0645 (5)0.0435 (5)0.0624 (5)−0.0110 (4)−0.0094 (4)0.0119 (4)
Br20.0602 (5)0.0741 (6)0.0529 (5)−0.0136 (4)0.0046 (4)−0.0175 (4)
Br30.0690 (6)0.0919 (7)0.0651 (5)−0.0507 (5)−0.0212 (5)0.0118 (5)
Br40.0817 (6)0.0751 (6)0.0438 (5)−0.0226 (5)−0.0222 (4)−0.0088 (4)
N10.045 (3)0.039 (3)0.029 (3)−0.016 (3)−0.006 (3)−0.008 (3)
N20.047 (3)0.040 (3)0.036 (3)−0.015 (3)−0.012 (3)−0.004 (3)
O10.045 (3)0.039 (3)0.037 (3)−0.004 (2)−0.003 (2)0.005 (2)
O20.067 (3)0.098 (4)0.036 (3)−0.049 (3)−0.005 (3)−0.008 (3)
S10.0536 (12)0.0460 (12)0.0376 (10)−0.0185 (9)0.0003 (9)−0.0019 (8)
S20.0445 (11)0.0661 (13)0.0423 (11)−0.0238 (10)−0.0031 (9)−0.0131 (9)
C10.048 (4)0.034 (4)0.044 (4)−0.008 (3)−0.021 (4)0.004 (3)
C20.035 (4)0.038 (4)0.034 (4)−0.010 (3)−0.009 (3)−0.007 (3)
C30.035 (4)0.043 (4)0.035 (4)−0.013 (3)−0.012 (3)−0.004 (3)
C40.043 (4)0.043 (4)0.034 (4)−0.014 (3)−0.008 (3)0.004 (3)
C50.047 (4)0.046 (5)0.038 (4)−0.018 (4)−0.012 (4)0.009 (3)
C60.043 (4)0.060 (5)0.039 (4)−0.024 (4)−0.007 (4)−0.009 (4)
C70.039 (4)0.032 (4)0.047 (4)−0.005 (3)−0.013 (4)−0.007 (3)
C80.041 (4)0.045 (5)0.031 (4)−0.022 (3)−0.016 (3)0.005 (3)
C90.045 (4)0.051 (5)0.039 (4)−0.024 (4)−0.019 (4)0.014 (4)
C100.060 (5)0.058 (5)0.043 (5)−0.024 (4)−0.009 (4)0.007 (4)
C110.064 (5)0.081 (7)0.066 (6)−0.045 (5)−0.027 (5)0.042 (5)
C120.053 (5)0.050 (5)0.082 (6)−0.023 (4)−0.031 (5)0.019 (5)
C130.059 (5)0.045 (5)0.059 (5)−0.022 (4)−0.023 (4)0.005 (4)
C140.043 (4)0.042 (4)0.041 (4)−0.019 (3)−0.011 (4)−0.002 (3)
C150.044 (4)0.044 (4)0.030 (4)−0.018 (3)−0.010 (3)0.003 (3)
C160.051 (5)0.048 (5)0.035 (4)−0.022 (4)−0.011 (4)0.004 (3)
C170.051 (5)0.047 (5)0.057 (5)−0.022 (4)−0.023 (4)0.010 (4)
C180.060 (5)0.045 (5)0.056 (5)−0.025 (4)−0.034 (4)0.004 (4)
C190.056 (5)0.043 (4)0.041 (4)−0.018 (4)−0.023 (4)0.001 (3)
C200.042 (4)0.036 (4)0.037 (4)−0.010 (3)−0.011 (3)0.001 (3)
C210.037 (4)0.041 (4)0.028 (4)−0.015 (3)−0.010 (3)−0.003 (3)
C220.042 (4)0.042 (4)0.030 (4)−0.020 (3)−0.006 (3)0.001 (3)
C230.052 (5)0.070 (5)0.035 (4)−0.033 (4)0.000 (4)−0.013 (4)
C240.075 (6)0.077 (6)0.051 (5)−0.047 (5)−0.030 (5)0.004 (4)
C250.043 (4)0.062 (5)0.051 (5)−0.027 (4)−0.006 (4)0.006 (4)
C260.044 (4)0.049 (5)0.040 (4)−0.019 (4)−0.005 (4)0.002 (3)
Geometric parameters (Å, º) top
Br1—C41.895 (6)C10—C111.381 (9)
Br2—C61.886 (6)C10—H100.9300
Br3—C171.882 (6)C11—C121.368 (10)
Br4—C191.886 (6)C11—H110.9300
N1—C11.265 (7)C12—C131.379 (9)
N1—C81.414 (7)C12—H120.9300
N2—C141.279 (7)C13—H130.9300
N2—C211.415 (7)C14—C151.458 (8)
O1—C31.333 (6)C14—H140.9300
O1—H10.8200C15—C201.386 (8)
O2—C161.337 (7)C15—C161.409 (8)
O2—H20.8200C16—C171.388 (9)
S1—C91.781 (6)C17—C181.370 (8)
S1—S22.025 (2)C18—C191.376 (8)
S2—C221.758 (6)C18—H180.9300
C1—C21.458 (8)C19—C201.373 (8)
C1—H1A0.9300C20—H200.9300
C2—C71.400 (8)C21—C261.387 (8)
C2—C31.408 (8)C21—C221.398 (8)
C3—C41.386 (8)C22—C231.372 (8)
C4—C51.378 (8)C23—C241.386 (8)
C5—C61.378 (8)C23—H230.9300
C5—H50.9300C24—C251.373 (9)
C6—C71.385 (8)C24—H240.9300
C7—H70.9300C25—C261.371 (9)
C8—C91.382 (8)C25—H250.9300
C8—C131.383 (8)C26—H260.9300
C9—C101.370 (8)
C1—N1—C8123.7 (5)C12—C13—C8119.2 (7)
C14—N2—C21122.5 (5)C12—C13—H13120.4
C3—O1—H1109.5C8—C13—H13120.4
C16—O2—H2109.5N2—C14—C15122.3 (6)
C9—S1—S2105.9 (2)N2—C14—H14118.9
C22—S2—S1105.3 (2)C15—C14—H14118.9
N1—C1—C2122.3 (6)C20—C15—C16119.2 (6)
N1—C1—H1A118.9C20—C15—C14120.5 (6)
C2—C1—H1A118.9C16—C15—C14120.3 (6)
C7—C2—C3119.6 (6)O2—C16—C17118.8 (6)
C7—C2—C1119.6 (6)O2—C16—C15122.4 (6)
C3—C2—C1120.8 (6)C17—C16—C15118.7 (6)
O1—C3—C4119.9 (6)C18—C17—C16120.7 (6)
O1—C3—C2121.9 (5)C18—C17—Br3120.2 (5)
C4—C3—C2118.2 (6)C16—C17—Br3119.1 (5)
C5—C4—C3122.3 (6)C17—C18—C19120.8 (6)
C5—C4—Br1119.5 (5)C17—C18—H18119.6
C3—C4—Br1118.2 (5)C19—C18—H18119.6
C6—C5—C4119.2 (6)C20—C19—C18119.4 (6)
C6—C5—H5120.4C20—C19—Br4120.7 (5)
C4—C5—H5120.4C18—C19—Br4119.9 (5)
C5—C6—C7120.5 (6)C19—C20—C15121.1 (6)
C5—C6—Br2119.6 (5)C19—C20—H20119.4
C7—C6—Br2119.9 (5)C15—C20—H20119.4
C6—C7—C2120.2 (6)C26—C21—C22119.9 (6)
C6—C7—H7119.9C26—C21—N2124.9 (6)
C2—C7—H7119.9C22—C21—N2115.1 (5)
C9—C8—C13119.7 (6)C23—C22—C21119.5 (6)
C9—C8—N1116.1 (6)C23—C22—S2124.2 (5)
C13—C8—N1124.2 (6)C21—C22—S2116.3 (5)
C10—C9—C8120.9 (6)C22—C23—C24120.0 (6)
C10—C9—S1123.7 (6)C22—C23—H23120.0
C8—C9—S1115.4 (5)C24—C23—H23120.0
C9—C10—C11119.0 (7)C25—C24—C23120.6 (7)
C9—C10—H10120.5C25—C24—H24119.7
C11—C10—H10120.5C23—C24—H24119.7
C12—C11—C10120.6 (7)C26—C25—C24120.0 (6)
C12—C11—H11119.7C26—C25—H25120.0
C10—C11—H11119.7C24—C25—H25120.0
C11—C12—C13120.5 (7)C25—C26—C21120.1 (6)
C11—C12—H12119.7C25—C26—H26120.0
C13—C12—H12119.7C21—C26—H26120.0
C9—S1—S2—C22−90.3 (3)C21—N2—C14—C15−179.5 (5)
C8—N1—C1—C2−178.9 (5)N2—C14—C15—C20178.4 (6)
N1—C1—C2—C7176.7 (6)N2—C14—C15—C16−1.9 (9)
N1—C1—C2—C3−1.4 (9)C20—C15—C16—O2−179.3 (6)
C7—C2—C3—O1177.8 (5)C14—C15—C16—O20.9 (9)
C1—C2—C3—O1−4.0 (9)C20—C15—C16—C17−0.3 (9)
C7—C2—C3—C4−1.6 (9)C14—C15—C16—C17180.0 (6)
C1—C2—C3—C4176.6 (5)O2—C16—C17—C18179.9 (6)
O1—C3—C4—C5−177.7 (5)C15—C16—C17—C180.9 (10)
C2—C3—C4—C51.7 (9)O2—C16—C17—Br3−0.8 (8)
O1—C3—C4—Br10.8 (8)C15—C16—C17—Br3−179.9 (4)
C2—C3—C4—Br1−179.8 (4)C16—C17—C18—C19−1.2 (10)
C3—C4—C5—C6−0.7 (9)Br3—C17—C18—C19179.5 (5)
Br1—C4—C5—C6−179.2 (5)C17—C18—C19—C201.0 (10)
C4—C5—C6—C7−0.5 (9)C17—C18—C19—Br4−178.4 (5)
C4—C5—C6—Br2177.3 (5)C18—C19—C20—C15−0.5 (9)
C5—C6—C7—C20.5 (9)Br4—C19—C20—C15179.0 (5)
Br2—C6—C7—C2−177.3 (4)C16—C15—C20—C190.1 (9)
C3—C2—C7—C60.6 (9)C14—C15—C20—C19179.9 (6)
C1—C2—C7—C6−177.6 (6)C14—N2—C21—C2631.8 (9)
C1—N1—C8—C9159.1 (6)C14—N2—C21—C22−151.8 (6)
C1—N1—C8—C13−22.2 (9)C26—C21—C22—C23−1.2 (9)
C13—C8—C9—C10−1.3 (9)N2—C21—C22—C23−177.8 (5)
N1—C8—C9—C10177.5 (5)C26—C21—C22—S2−178.4 (4)
C13—C8—C9—S1177.3 (4)N2—C21—C22—S25.0 (7)
N1—C8—C9—S1−4.0 (7)S1—S2—C22—C2315.4 (6)
S2—S1—C9—C1010.7 (6)S1—S2—C22—C21−167.6 (4)
S2—S1—C9—C8−167.8 (4)C21—C22—C23—C241.5 (10)
C8—C9—C10—C110.5 (10)S2—C22—C23—C24178.4 (5)
S1—C9—C10—C11−177.8 (5)C22—C23—C24—C25−0.5 (10)
C9—C10—C11—C121.3 (10)C23—C24—C25—C26−0.7 (10)
C10—C11—C12—C13−2.5 (11)C24—C25—C26—C210.9 (10)
C11—C12—C13—C81.8 (10)C22—C21—C26—C250.0 (9)
C9—C8—C13—C120.1 (9)N2—C21—C26—C25176.3 (6)
N1—C8—C13—C12−178.5 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C11—H11···Br3i0.933.063.942 (7)158
C1—H1A···Br4ii0.933.013.753 (6)138
Symmetry codes: (i) x, y−1, z; (ii) x+1, y−1, z−1.

Experimental details

Crystal data
Chemical formulaC26H16Br4N2O2S2
Mr772.17
Crystal system, space groupTriclinic, P1
Temperature (K)298
a, b, c (Å)10.4361 (17), 11.4199 (18), 12.938 (2)
α, β, γ (°)89.721 (3), 71.536 (2), 68.211 (2)
V (Å3)1346.9 (4)
Z2
Radiation typeMo Kα
µ (mm−1)6.16
Crystal size (mm)0.28 × 0.16 × 0.10
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.277, 0.578
No. of measured, independent and
observed [I > 2σ(I)] reflections		7083, 4705, 2583
Rint0.034
(sin θ/λ)max (Å−1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.103, 1.00
No. of reflections4705
No. of parameters325
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.67, −0.52

Computer programs: SMART (Bruker, 2001), SMART, SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C11—H11···Br3i0.933.063.942 (7)158.3
C1—H1A···Br4ii0.933.013.753 (6)138.1
Symmetry codes: (i) x, y−1, z; (ii) x+1, y−1, z−1.
 

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