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The title compound, C15H13BrN2S2, crystallizes with two independent mol­ecules in the asymmetric unit. Both mol­ecules display a `C-shaped' conformation, with a trans configuration with respect to the C=N double bond. Inter­molecular N—H...S inter­actions are observed.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807050209/bi2244sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807050209/bi2244Isup2.hkl
Contains datablock I

CCDC reference: 667372

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.011 Å
  • R factor = 0.044
  • wR factor = 0.122
  • Data-to-parameter ratio = 15.0

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 32 Perc. PLAT331_ALERT_2_B Small Average Phenyl C-C Dist. C25 -C30 1.36 Ang.
Alert level C GOODF01_ALERT_2_C The least squares goodness of fit parameter lies outside the range 0.80 <> 2.00 Goodness of fit given = 0.792 RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.105 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.10 PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C9 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C26 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C27 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C8 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C10 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C16 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C25 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C28 PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C10 -C15 1.37 Ang. PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 11
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 14 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 11 ALERT type 2 Indicator that the structure model may be wrong or deficient 5 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

As an extension of our work on the structural characterization of Schiff-base compounds (Qiu, Fang et al., 2006; Qiu, Luo et al., 2006), we report here the crystal structure of the title compound. The asymmetric unit consists of two independent molecules (Fig. 1), both of which display a "C-shaped" conformation. In both independent molecules, all bond lengths and angles lie within normal ranges: the C7=N1 and C22=N3 bond lengths of 1.272 (7) and 1.257 (7) Å conform to the expected value for a C=N double bond. The bond lengths of 1.324 (6) and 1.338 (7) Å for C8—N2 and C23—N4, respectively, lie between the expected values for a double and single bond, because of conjugation effects in the molecule. The dihedral angle between the two benzene rings in each molecule is 107.9 (6) and 105.1 (6) ° for the two independent molecules, respectively. In the crystal, intermolecular N—H···S interactions are observed.

Related literature top

For related Schiff base structures, see: Qiu, Fang et al. (2006); Qiu, Luo, et al. (2006).

Experimental top

The title compound was synthesized by reaction of equivalent amounts of S-benzyldithiocarbazate (1 mmol, 0.20 g) and 2-bromobenzaldehyde (1 mmol, 0.19 g) in ethanol (20 ml) for 1 h at 373–383 K. Single crystals suitable for X-ray diffraction analysis were obtained by slow evaporation of an ethanol solution.

Refinement top

Atoms H2 and H4 were visible in a difference Fourier map, but were placed in calculated positions (N—H = 0.86 Å) and refined as riding with Uiso(H) = 1.2Ueq(N). All other H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms with C—H distances of 0.93 or 0.97 Å and with Uiso(H) = 1.2Ueq(C). The higher-angle diffraction data were weak, with only 1750 out of 5399 unique reflections observed (I > 2σ(I)) to θmax = 25.0°, and the resulting structure is of relatively low precision.

Structure description top

As an extension of our work on the structural characterization of Schiff-base compounds (Qiu, Fang et al., 2006; Qiu, Luo et al., 2006), we report here the crystal structure of the title compound. The asymmetric unit consists of two independent molecules (Fig. 1), both of which display a "C-shaped" conformation. In both independent molecules, all bond lengths and angles lie within normal ranges: the C7=N1 and C22=N3 bond lengths of 1.272 (7) and 1.257 (7) Å conform to the expected value for a C=N double bond. The bond lengths of 1.324 (6) and 1.338 (7) Å for C8—N2 and C23—N4, respectively, lie between the expected values for a double and single bond, because of conjugation effects in the molecule. The dihedral angle between the two benzene rings in each molecule is 107.9 (6) and 105.1 (6) ° for the two independent molecules, respectively. In the crystal, intermolecular N—H···S interactions are observed.

For related Schiff base structures, see: Qiu, Fang et al. (2006); Qiu, Luo, et al. (2006).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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 (Bruker, 1997).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound showing displacement ellipsoids at 30% for non-H atoms. Dashed lines denote N—H···S hydrogen bonds.
S-Benzyl 3-(2-bromobenzylidene)dithiocarbazate top
Crystal data top
C15H13BrN2S2F(000) = 1472
Mr = 365.30Dx = 1.540 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3876 reflections
a = 22.465 (6) Åθ = 4.2–25°
b = 5.9323 (17) ŵ = 2.86 mm1
c = 23.668 (7) ÅT = 298 K
β = 92.432 (5)°Block, yellow
V = 3151.4 (16) Å30.12 × 0.07 × 0.06 mm
Z = 8
Data collection top
Bruker SMART APEX CCD
diffractometer
5399 independent reflections
Radiation source: fine-focus sealed tube1750 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.105
ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2626
Tmin = 0.725, Tmax = 0.847k = 66
17549 measured reflectionsl = 2827
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122H-atom parameters constrained
S = 0.79 w = 1/[σ2(Fo2) + (0.0502P)2]
where P = (Fo2 + 2Fc2)/3
5399 reflections(Δ/σ)max = 0.001
361 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.31 e Å3
Crystal data top
C15H13BrN2S2V = 3151.4 (16) Å3
Mr = 365.30Z = 8
Monoclinic, P21/nMo Kα radiation
a = 22.465 (6) ŵ = 2.86 mm1
b = 5.9323 (17) ÅT = 298 K
c = 23.668 (7) Å0.12 × 0.07 × 0.06 mm
β = 92.432 (5)°
Data collection top
Bruker SMART APEX CCD
diffractometer
5399 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
1750 reflections with I > 2σ(I)
Tmin = 0.725, Tmax = 0.847Rint = 0.105
17549 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.122H-atom parameters constrained
S = 0.79Δρmax = 0.26 e Å3
5399 reflectionsΔρmin = 0.31 e Å3
361 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
Br10.38156 (4)0.81077 (15)1.06812 (3)0.1124 (4)
Br20.43680 (3)1.27449 (14)0.61505 (4)0.1031 (3)
C10.3175 (3)0.7293 (14)1.0175 (3)0.077 (2)
C20.3203 (3)0.5446 (11)0.9824 (3)0.0654 (18)
C30.2709 (3)0.4962 (12)0.9467 (3)0.083 (2)
H3A0.27110.36990.92340.099*
C40.2221 (3)0.6354 (15)0.9459 (3)0.102 (3)
H4A0.19000.60460.92100.123*
C50.2195 (4)0.8175 (14)0.9808 (3)0.101 (3)
H5A0.18560.90740.98110.122*
C60.2683 (4)0.8640 (13)1.0155 (3)0.098 (2)
H6A0.26790.99151.03830.117*
C70.3727 (3)0.3955 (12)0.9836 (3)0.0703 (19)
H7A0.40270.41351.01150.084*
C80.4342 (2)0.0640 (12)0.9179 (2)0.0659 (18)
C90.4007 (3)0.3370 (11)0.8268 (3)0.085 (2)
H9A0.44180.31700.81680.102*
H9B0.39840.47070.85020.102*
C100.3617 (3)0.3658 (12)0.7741 (3)0.0601 (17)
C110.3642 (3)0.2141 (12)0.7310 (3)0.082 (2)
H11A0.38810.08680.73530.098*
C120.3316 (4)0.2477 (14)0.6813 (3)0.101 (3)
H12A0.33390.14480.65180.121*
C130.2960 (3)0.4325 (18)0.6755 (3)0.100 (3)
H13A0.27360.45420.64200.120*
C140.2928 (3)0.5855 (13)0.7178 (4)0.091 (2)
H14A0.26810.71080.71340.110*
C150.3257 (3)0.5547 (12)0.7667 (3)0.075 (2)
H15A0.32410.66110.79550.090*
C160.4832 (3)1.1731 (14)0.6791 (3)0.0723 (19)
C170.5172 (3)0.9776 (13)0.6768 (3)0.075 (2)
C180.5487 (3)0.9139 (13)0.7264 (3)0.095 (2)
H18A0.57250.78550.72680.114*
C190.5445 (4)1.0426 (17)0.7755 (3)0.109 (3)
H19A0.56500.99700.80850.131*
C200.5111 (4)1.2324 (16)0.7760 (3)0.106 (3)
H20A0.50881.31710.80880.128*
C210.4808 (3)1.2978 (12)0.7275 (4)0.092 (2)
H21A0.45811.42910.72740.110*
C220.5213 (3)0.8447 (12)0.6253 (3)0.071 (2)
H22A0.49550.87560.59460.085*
C230.5898 (3)0.3934 (12)0.5621 (2)0.0720 (19)
C240.6815 (3)0.0966 (11)0.5928 (2)0.080 (2)
H24A0.65550.03330.58820.096*
H24B0.69740.13210.55630.096*
C250.7320 (3)0.0452 (14)0.6356 (3)0.075 (2)
C260.7806 (4)0.1761 (14)0.6396 (3)0.127 (3)
H26A0.78310.30180.61630.153*
C270.8270 (4)0.1273 (18)0.6777 (4)0.144 (4)
H27A0.86000.22170.68030.173*
C280.8248 (4)0.0578 (18)0.7116 (3)0.110 (3)
H28A0.85600.09040.73740.133*
C290.7776 (5)0.1902 (14)0.7070 (3)0.111 (3)
H29A0.77610.31920.72930.133*
C300.7304 (3)0.1405 (13)0.6698 (3)0.084 (2)
H30A0.69720.23410.66800.101*
N10.3769 (2)0.2421 (10)0.9464 (2)0.0724 (15)
N20.4263 (2)0.1106 (10)0.9516 (2)0.0770 (16)
H20.45320.14150.97740.092*
N30.5589 (2)0.6892 (10)0.6216 (2)0.0774 (17)
N40.5567 (2)0.5759 (10)0.5714 (2)0.0795 (17)
H40.53290.62390.54460.095*
S10.49163 (8)0.2385 (3)0.92583 (7)0.0950 (7)
S20.37642 (7)0.0936 (3)0.86578 (7)0.0773 (6)
S30.58178 (8)0.2452 (3)0.50331 (7)0.0931 (6)
S40.64041 (7)0.3345 (3)0.61861 (7)0.0773 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.1210 (7)0.1233 (8)0.0901 (6)0.0066 (6)0.0297 (5)0.0369 (5)
Br20.0768 (5)0.1047 (7)0.1263 (7)0.0116 (5)0.0130 (5)0.0037 (5)
C10.080 (5)0.100 (7)0.052 (4)0.017 (5)0.001 (4)0.007 (4)
C20.084 (5)0.058 (5)0.053 (4)0.017 (4)0.006 (4)0.004 (4)
C30.083 (5)0.091 (6)0.072 (5)0.005 (5)0.016 (4)0.027 (4)
C40.079 (6)0.107 (7)0.118 (7)0.039 (5)0.022 (5)0.008 (6)
C50.100 (7)0.087 (7)0.117 (7)0.044 (5)0.002 (5)0.019 (5)
C60.112 (7)0.096 (7)0.083 (6)0.020 (6)0.004 (5)0.027 (5)
C70.074 (5)0.065 (5)0.071 (5)0.007 (4)0.014 (4)0.004 (4)
C80.051 (4)0.082 (5)0.064 (4)0.013 (4)0.013 (3)0.012 (4)
C90.074 (5)0.084 (5)0.095 (5)0.026 (4)0.018 (4)0.022 (4)
C100.063 (4)0.057 (5)0.060 (5)0.014 (4)0.004 (4)0.002 (4)
C110.092 (5)0.080 (6)0.073 (5)0.024 (4)0.009 (4)0.005 (5)
C120.129 (7)0.091 (7)0.082 (6)0.004 (6)0.005 (5)0.018 (5)
C130.097 (7)0.128 (9)0.071 (6)0.023 (6)0.031 (5)0.027 (6)
C140.067 (5)0.077 (6)0.127 (7)0.009 (4)0.023 (5)0.012 (6)
C150.084 (5)0.057 (6)0.084 (6)0.001 (4)0.001 (4)0.013 (4)
C160.062 (5)0.069 (6)0.085 (6)0.019 (4)0.001 (4)0.007 (5)
C170.078 (5)0.065 (6)0.082 (6)0.005 (4)0.002 (5)0.012 (5)
C180.103 (6)0.090 (6)0.091 (6)0.022 (5)0.018 (5)0.011 (5)
C190.124 (7)0.122 (8)0.079 (6)0.014 (6)0.023 (5)0.026 (6)
C200.109 (7)0.116 (8)0.093 (7)0.023 (6)0.006 (5)0.030 (6)
C210.072 (5)0.083 (6)0.121 (7)0.000 (4)0.003 (5)0.010 (6)
C220.063 (5)0.077 (6)0.070 (5)0.008 (4)0.014 (4)0.003 (4)
C230.075 (5)0.078 (6)0.061 (4)0.012 (4)0.014 (4)0.009 (4)
C240.087 (5)0.079 (5)0.073 (5)0.001 (4)0.008 (4)0.013 (4)
C250.080 (6)0.071 (6)0.074 (5)0.003 (5)0.007 (4)0.010 (5)
C260.123 (7)0.142 (8)0.112 (7)0.056 (7)0.055 (6)0.060 (6)
C270.107 (7)0.183 (11)0.138 (8)0.075 (7)0.055 (6)0.060 (7)
C280.100 (7)0.132 (9)0.097 (7)0.031 (6)0.026 (6)0.006 (6)
C290.149 (9)0.088 (7)0.092 (6)0.008 (7)0.028 (6)0.021 (5)
C300.090 (6)0.056 (6)0.106 (6)0.011 (4)0.004 (5)0.005 (5)
N10.072 (4)0.071 (4)0.072 (4)0.026 (3)0.018 (3)0.016 (3)
N20.061 (4)0.087 (5)0.081 (4)0.014 (3)0.025 (3)0.023 (3)
N30.071 (4)0.081 (5)0.080 (4)0.004 (3)0.004 (3)0.010 (4)
N40.088 (4)0.082 (5)0.067 (4)0.009 (4)0.021 (3)0.016 (4)
S10.0782 (13)0.1111 (17)0.0922 (14)0.0329 (12)0.0366 (11)0.0305 (12)
S20.0734 (12)0.0855 (14)0.0711 (11)0.0169 (10)0.0206 (9)0.0137 (10)
S30.0904 (13)0.1104 (17)0.0763 (12)0.0126 (12)0.0227 (10)0.0276 (12)
S40.0794 (12)0.0836 (14)0.0674 (11)0.0011 (10)0.0161 (9)0.0111 (10)
Geometric parameters (Å, º) top
Br1—C11.895 (7)C16—C171.391 (8)
Br2—C161.901 (7)C17—C181.397 (8)
C1—C61.363 (8)C17—C221.457 (8)
C1—C21.379 (8)C18—C191.397 (8)
C2—C31.396 (7)C18—H18A0.930
C2—C71.471 (8)C19—C201.353 (9)
C3—C41.372 (8)C19—H19A0.930
C3—H3A0.930C20—C211.366 (9)
C4—C51.362 (9)C20—H20A0.930
C4—H4A0.930C21—H21A0.930
C5—C61.370 (8)C22—N31.257 (7)
C5—H5A0.930C22—H22A0.930
C6—H6A0.930C23—N41.338 (7)
C7—N11.272 (7)C23—S31.650 (6)
C7—H7A0.930C23—S41.752 (6)
C8—N21.324 (6)C24—C251.520 (8)
C8—S11.659 (6)C24—S41.808 (6)
C8—S21.761 (5)C24—H24A0.970
C9—C101.502 (7)C24—H24B0.970
C9—S21.810 (6)C25—C261.339 (8)
C9—H9A0.970C25—C301.369 (8)
C9—H9B0.970C26—C271.381 (9)
C10—C111.363 (8)C26—H26A0.930
C10—C151.389 (8)C27—C281.361 (10)
C11—C121.373 (9)C27—H27A0.930
C11—H11A0.930C28—C291.320 (10)
C12—C131.360 (9)C28—H28A0.930
C12—H12A0.930C29—C301.381 (9)
C13—C141.356 (9)C29—H29A0.930
C13—H13A0.930C30—H30A0.930
C14—C151.359 (8)N1—N21.359 (6)
C14—H14A0.930N2—H20.860
C15—H15A0.930N3—N41.364 (6)
C16—C211.366 (8)N4—H40.860
C6—C1—C2120.1 (6)C18—C17—C22120.6 (7)
C6—C1—Br1117.8 (6)C17—C18—C19120.1 (7)
C2—C1—Br1122.1 (6)C17—C18—H18A119.9
C1—C2—C3118.2 (6)C19—C18—H18A119.9
C1—C2—C7121.5 (7)C20—C19—C18121.2 (8)
C3—C2—C7120.2 (6)C20—C19—H19A119.4
C4—C3—C2119.9 (7)C18—C19—H19A119.4
C4—C3—H3A120.0C19—C20—C21119.2 (8)
C2—C3—H3A120.0C19—C20—H20A120.4
C5—C4—C3121.6 (7)C21—C20—H20A120.4
C5—C4—H4A119.2C20—C21—C16120.9 (7)
C3—C4—H4A119.2C20—C21—H21A119.5
C4—C5—C6117.9 (7)C16—C21—H21A119.5
C4—C5—H5A121.0N3—C22—C17121.5 (7)
C6—C5—H5A121.0N3—C22—H22A119.2
C1—C6—C5122.1 (7)C17—C22—H22A119.2
C1—C6—H6A119.0N4—C23—S3121.8 (5)
C5—C6—H6A119.0N4—C23—S4112.6 (5)
N1—C7—C2119.9 (6)S3—C23—S4125.6 (5)
N1—C7—H7A120.0C25—C24—S4108.0 (4)
C2—C7—H7A120.0C25—C24—H24A110.1
N2—C8—S1122.9 (5)S4—C24—H24A110.1
N2—C8—S2112.8 (4)C25—C24—H24B110.1
S1—C8—S2124.3 (4)S4—C24—H24B110.1
C10—C9—S2109.7 (4)H24A—C24—H24B108.4
C10—C9—H9A109.7C26—C25—C30117.9 (7)
S2—C9—H9A109.7C26—C25—C24120.9 (8)
C10—C9—H9B109.7C30—C25—C24121.2 (7)
S2—C9—H9B109.7C25—C26—C27121.0 (8)
H9A—C9—H9B108.2C25—C26—H26A119.5
C11—C10—C15118.7 (6)C27—C26—H26A119.5
C11—C10—C9120.3 (7)C28—C27—C26120.6 (8)
C15—C10—C9120.8 (7)C28—C27—H27A119.7
C10—C11—C12120.5 (7)C26—C27—H27A119.7
C10—C11—H11A119.7C29—C28—C27118.8 (8)
C12—C11—H11A119.7C29—C28—H28A120.6
C13—C12—C11119.5 (7)C27—C28—H28A120.6
C13—C12—H12A120.2C28—C29—C30121.1 (8)
C11—C12—H12A120.2C28—C29—H29A119.4
C14—C13—C12121.0 (8)C30—C29—H29A119.4
C14—C13—H13A119.5C25—C30—C29120.7 (7)
C12—C13—H13A119.5C25—C30—H30A119.7
C13—C14—C15119.6 (7)C29—C30—H30A119.7
C13—C14—H14A120.2C7—N1—N2115.6 (5)
C15—C14—H14A120.2C8—N2—N1121.6 (5)
C14—C15—C10120.6 (6)C8—N2—H2119.2
C14—C15—H15A119.7N1—N2—H2119.2
C10—C15—H15A119.7C22—N3—N4115.0 (6)
C21—C16—C17121.7 (7)C23—N4—N3122.8 (6)
C21—C16—Br2117.2 (7)C23—N4—H4118.6
C17—C16—Br2121.1 (6)N3—N4—H4118.6
C16—C17—C18116.9 (7)C8—S2—C9102.0 (3)
C16—C17—C22122.5 (7)C23—S4—C24102.8 (3)
C6—C1—C2—C32.4 (10)C18—C19—C20—C210.4 (13)
Br1—C1—C2—C3179.6 (5)C19—C20—C21—C160.8 (12)
C6—C1—C2—C7179.9 (6)C17—C16—C21—C201.1 (11)
Br1—C1—C2—C72.1 (9)Br2—C16—C21—C20177.7 (6)
C1—C2—C3—C42.1 (10)C16—C17—C22—N3169.0 (6)
C7—C2—C3—C4179.7 (6)C18—C17—C22—N310.0 (10)
C2—C3—C4—C52.3 (12)S4—C24—C25—C2675.2 (8)
C3—C4—C5—C62.6 (13)S4—C24—C25—C30107.2 (6)
C2—C1—C6—C52.8 (11)C30—C25—C26—C271.1 (13)
Br1—C1—C6—C5179.1 (6)C24—C25—C26—C27178.8 (7)
C4—C5—C6—C12.8 (12)C25—C26—C27—C281.1 (15)
C1—C2—C7—N1172.1 (6)C26—C27—C28—C290.3 (15)
C3—C2—C7—N110.5 (10)C27—C28—C29—C301.6 (14)
S2—C9—C10—C1168.9 (7)C26—C25—C30—C290.2 (11)
S2—C9—C10—C15115.6 (6)C24—C25—C30—C29177.5 (6)
C15—C10—C11—C120.0 (10)C28—C29—C30—C251.6 (13)
C9—C10—C11—C12175.6 (6)C2—C7—N1—N2178.9 (5)
C10—C11—C12—C130.9 (11)S1—C8—N2—N1175.6 (5)
C11—C12—C13—C140.8 (12)S2—C8—N2—N12.7 (8)
C12—C13—C14—C150.3 (12)C7—N1—N2—C8175.6 (6)
C13—C14—C15—C101.3 (11)C17—C22—N3—N4178.6 (5)
C11—C10—C15—C141.2 (10)S3—C23—N4—N3174.1 (4)
C9—C10—C15—C14176.7 (6)S4—C23—N4—N35.5 (8)
C21—C16—C17—C180.2 (10)C22—N3—N4—C23173.9 (6)
Br2—C16—C17—C18178.5 (5)N2—C8—S2—C9178.8 (5)
C21—C16—C17—C22178.8 (6)S1—C8—S2—C92.9 (5)
Br2—C16—C17—C222.5 (9)C10—C9—S2—C8170.6 (5)
C16—C17—C18—C190.9 (10)N4—C23—S4—C24176.3 (5)
C22—C17—C18—C19180.0 (7)S3—C23—S4—C244.1 (5)
C17—C18—C19—C201.2 (12)C25—C24—S4—C23173.6 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4···S3i0.862.883.669 (5)154
N2—H2···S1ii0.862.623.455 (5)164
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y, z+2.

Experimental details

Crystal data
Chemical formulaC15H13BrN2S2
Mr365.30
Crystal system, space groupMonoclinic, P21/n
Temperature (K)298
a, b, c (Å)22.465 (6), 5.9323 (17), 23.668 (7)
β (°) 92.432 (5)
V3)3151.4 (16)
Z8
Radiation typeMo Kα
µ (mm1)2.86
Crystal size (mm)0.12 × 0.07 × 0.06
Data collection
DiffractometerBruker SMART APEX CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.725, 0.847
No. of measured, independent and
observed [I > 2σ(I)] reflections
17549, 5399, 1750
Rint0.105
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.122, 0.79
No. of reflections5399
No. of parameters361
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.26, 0.31

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4···S3i0.862.883.669 (5)153.9
N2—H2···S1ii0.862.623.455 (5)163.5
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y, z+2.
 

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