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The two bromo­phenyl rings in the title compound, C13H10Br2N2S, adopt a ciscis configuration to S with respect to the C—N thio­urea bonds. The crystal packing is characterized by N—H...S hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806056479/om2078sup1.cif
Contains datablocks DATNAM, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806056479/om2078Isup2.hkl
Contains datablock I

CCDC reference: 638521

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.028
  • wR factor = 0.072
  • Data-to-parameter ratio = 16.3

checkCIF/PLATON results

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Alert level B PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.50 Ratio
Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.29 PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct... 8 PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3 PLAT431_ALERT_2_C Short Inter HL..A Contact Br1 .. Br2 .. 3.54 Ang.
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 4 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 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus and XPREP (Bruker, 2001); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

(I) top
Crystal data top
C13H10Br2N2SF(000) = 752
Mr = 386.11The final unit cell was obtained from the xyz centroids of 5020 reflections after integration using the SAINTPLUS software package (Bruker, 2000).
Reduced cell calculations did not indicate any higher metric lattice symmetry and examination of the finalatomic coordinates of the structure did not yield extra symmetry elements (Spek, 1988; Le Page 1987, 1988)
Monoclinic, P21/cDx = 1.887 Mg m3
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 14.077 (1) ÅCell parameters from 5020 reflections
b = 7.0804 (6) Åθ = 2.9–29.4°
c = 14.054 (1) ŵ = 6.10 mm1
β = 104.026 (1)°T = 100 K
V = 1359.01 (18) Å3Block, colorless
Z = 40.46 × 0.42 × 0.37 mm
Data collection top
Bruker SMART Apex
diffractometer
3318 independent reflections
Radiation source: fine focus sealed Siemens Mo tube2769 reflections with I > 2σ(I)
Parallel mounted graphite monochromatorRint = 0.029
Detector resolution: 4096x4096 / 62x62 (binned 512) pixels mm-1θmax = 28.3°, θmin = 3.0°
φ and ω scansh = 1818
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
k = 99
Tmin = 0.073, Tmax = 0.106l = 1518
10894 measured reflections
Refinement top
Refinement on F2Primary atom site location: heavy-atom method
Least-squares matrix: fullSecondary atom site location: structure-invariant direct methods
R[F2 > 2σ(F2)] = 0.028Hydrogen site location: difference Fourier map
wR(F2) = 0.072All H-atom parameters refined
S = 1.04 w = 1/[σ2(Fo2) + (0.0404P)2 + 0.2476P]
where P = (Fo2 + 2Fc2)/3
3318 reflections(Δ/σ)max = 0.001
203 parametersΔρmax = 0.95 e Å3
0 restraintsΔρmin = 0.42 e Å3
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
Br10.36823 (2)0.19030 (3)0.51761 (2)0.0285 (1)
Br20.46781 (2)0.19606 (3)0.16394 (2)0.0269 (1)
S0.08535 (4)0.15939 (7)0.39401 (4)0.0150 (1)
N10.04879 (13)0.4225 (3)0.31854 (13)0.0157 (5)
N20.09041 (13)0.4346 (3)0.26553 (13)0.0165 (5)
C10.09820 (16)0.3287 (3)0.46781 (17)0.0168 (6)
C20.17251 (16)0.2784 (3)0.51259 (18)0.0185 (6)
C30.26763 (16)0.2620 (3)0.45654 (18)0.0190 (6)
C40.29103 (17)0.2971 (3)0.35681 (18)0.0205 (6)
C50.21641 (16)0.3469 (3)0.31242 (17)0.0175 (6)
C60.12027 (15)0.3619 (3)0.36726 (16)0.0149 (6)
C70.04089 (14)0.3482 (3)0.32398 (15)0.0138 (6)
C80.18026 (14)0.3759 (3)0.24581 (16)0.0157 (6)
C90.18244 (15)0.3507 (3)0.14874 (16)0.0153 (5)
C100.26821 (16)0.3002 (3)0.12420 (18)0.0181 (6)
C110.35179 (15)0.2735 (3)0.19824 (17)0.0185 (6)
C120.35166 (17)0.2991 (3)0.29596 (18)0.0207 (6)
C130.26545 (16)0.3522 (3)0.31977 (17)0.0188 (6)
H10.0312 (16)0.340 (3)0.5055 (17)0.008 (5)*
H20.1601 (18)0.251 (3)0.5822 (18)0.017 (6)*
H40.356 (2)0.286 (3)0.319 (2)0.028 (7)*
H50.2302 (16)0.377 (3)0.2480 (18)0.015 (6)*
H90.1236 (17)0.374 (3)0.1001 (17)0.015 (6)*
H100.272 (2)0.287 (4)0.060 (2)0.027 (7)*
H120.411 (2)0.285 (3)0.346 (2)0.026 (7)*
H130.2597 (17)0.378 (3)0.3902 (19)0.022 (6)*
H210.0697 (16)0.492 (3)0.2746 (18)0.017 (6)*
H220.055 (2)0.495 (4)0.224 (2)0.036 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0248 (1)0.0338 (2)0.0324 (2)0.0052 (1)0.0178 (1)0.0010 (1)
Br20.0177 (1)0.0320 (1)0.0337 (2)0.0020 (1)0.0117 (1)0.0026 (1)
S0.0178 (2)0.0136 (2)0.0137 (3)0.0010 (2)0.0038 (2)0.0013 (2)
N10.0190 (8)0.0143 (8)0.0146 (9)0.0038 (7)0.0058 (7)0.0054 (7)
N20.0183 (8)0.0165 (9)0.0160 (10)0.0027 (7)0.0068 (7)0.0046 (7)
C10.0208 (10)0.0130 (9)0.0174 (11)0.0002 (8)0.0065 (9)0.0008 (8)
C20.0232 (11)0.0163 (10)0.0181 (12)0.0006 (8)0.0092 (9)0.0001 (9)
C30.0210 (10)0.0149 (9)0.0257 (12)0.0003 (8)0.0145 (9)0.0017 (9)
C40.0173 (10)0.0212 (11)0.0232 (12)0.0006 (8)0.0052 (9)0.0014 (9)
C50.0217 (10)0.0165 (10)0.0151 (11)0.0027 (8)0.0058 (9)0.0011 (8)
C60.0186 (10)0.0110 (9)0.0176 (11)0.0020 (8)0.0094 (8)0.0009 (8)
C70.0184 (10)0.0126 (9)0.0102 (10)0.0016 (7)0.0030 (8)0.0037 (7)
C80.0165 (9)0.0128 (9)0.0189 (11)0.0001 (8)0.0065 (8)0.0012 (8)
C90.0156 (9)0.0148 (9)0.0148 (10)0.0006 (8)0.0022 (8)0.0017 (8)
C100.0214 (10)0.0178 (10)0.0166 (12)0.0031 (8)0.0077 (9)0.0016 (8)
C110.0144 (9)0.0157 (10)0.0274 (13)0.0012 (8)0.0092 (9)0.0001 (9)
C120.0186 (10)0.0249 (11)0.0181 (12)0.0025 (8)0.0034 (9)0.0016 (9)
C130.0205 (10)0.0209 (10)0.0156 (11)0.0025 (8)0.0055 (9)0.0005 (9)
Geometric parameters (Å, º) top
Br1—C31.895 (2)C8—C131.394 (3)
Br2—C111.893 (2)C8—C91.384 (3)
S—C71.688 (2)C9—C101.381 (3)
N1—C61.414 (3)C10—C111.382 (3)
N1—C71.353 (3)C11—C121.386 (3)
N2—C71.346 (3)C12—C131.387 (3)
N2—C81.421 (3)C1—H10.97 (2)
N1—H210.79 (2)C2—H20.97 (2)
N2—H220.79 (3)C4—H40.94 (3)
C1—C61.391 (3)C5—H50.90 (2)
C1—C21.392 (3)C9—H90.95 (2)
C2—C31.384 (3)C10—H100.92 (3)
C3—C41.382 (3)C12—H120.96 (3)
C4—C51.391 (3)C13—H131.03 (3)
C5—C61.390 (3)
Br1···Br2i3.5362 (5)C9···C4viii3.520 (3)
Br2···Br1ii3.5362 (5)C9···C5viii3.570 (3)
Br2···C4iii3.729 (2)C10···Six3.625 (3)
Br2···C12iv3.739 (2)C10···C3viii3.460 (3)
Br2···H4v2.95 (3)C10···C4iii3.581 (3)
S···C13.239 (2)C10···C4viii3.537 (3)
S···C133.265 (2)C10···C5iii3.456 (3)
S···N2iii3.316 (2)C11···C5iii3.555 (3)
S···C9vi3.510 (2)C11···C4iii3.520 (3)
S···N1iii3.355 (2)C12···Br2x3.739 (2)
S···C2vii3.472 (2)C13···S3.265 (2)
S···C10vi3.625 (3)C1···H1xi2.94 (2)
S···H21iii2.61 (2)C7···H22iii2.84 (3)
S···H22iii2.53 (3)C7···H12.97 (2)
S···H2vii3.08 (2)C7···H133.00 (3)
S···H132.91 (2)C7···H21iii2.95 (2)
S···H12.83 (2)H1···S2.83 (2)
S···H9vi2.83 (2)H1···C72.97 (2)
S···H10vi3.09 (3)H1···C1xi2.94 (2)
N1···Sviii3.355 (2)H1···H1xi2.45 (3)
N2···Sviii3.316 (2)H2···Svii3.08 (2)
C1···S3.239 (2)H4···Br2xii2.95 (3)
C2···Svii3.472 (2)H5···H212.35 (3)
C3···C10iii3.460 (3)H9···H222.35 (4)
C4···C11viii3.520 (3)H9···Six2.83 (2)
C4···Br2viii3.729 (2)H10···Six3.09 (3)
C4···C9iii3.520 (3)H13···S2.91 (2)
C4···C10iii3.537 (3)H13···C73.00 (3)
C4···C10viii3.581 (3)H21···H52.35 (3)
C5···C10viii3.456 (3)H21···H222.05 (4)
C5···C8iii3.500 (3)H21···Sviii2.61 (2)
C5···C9iii3.570 (3)H21···C7viii2.95 (2)
C5···C11viii3.555 (3)H22···H92.35 (4)
C6···C9viii3.564 (3)H22···H212.05 (4)
C8···C5viii3.500 (3)H22···Sviii2.53 (3)
C9···Six3.510 (2)H22···C7viii2.84 (3)
C9···C6iii3.564 (3)
C6—N1—C7128.21 (19)C9—C10—C11118.9 (2)
C7—N2—C8127.1 (2)Br2—C11—C10118.53 (17)
C6—N1—H21113.2 (17)C10—C11—C12121.5 (2)
C7—N1—H21116.9 (17)Br2—C11—C12119.92 (17)
C7—N2—H22112 (2)C11—C12—C13119.1 (2)
C8—N2—H22116 (2)C8—C13—C12119.9 (2)
C2—C1—C6119.7 (2)C2—C1—H1120.9 (14)
C1—C2—C3119.6 (2)C6—C1—H1119.4 (14)
Br1—C3—C2119.40 (18)C1—C2—H2122.4 (16)
Br1—C3—C4119.14 (18)C3—C2—H2118.0 (15)
C2—C3—C4121.5 (2)C3—C4—H4121.1 (17)
C3—C4—C5118.7 (2)C5—C4—H4120.2 (17)
C4—C5—C6120.7 (2)C4—C5—H5120.4 (15)
N1—C6—C1122.2 (2)C6—C5—H5118.8 (15)
N1—C6—C5117.79 (19)C8—C9—H9117.5 (15)
C1—C6—C5119.9 (2)C10—C9—H9121.8 (15)
N1—C7—N2113.76 (19)C9—C10—H10122.2 (18)
S—C7—N1123.37 (16)C11—C10—H10118.9 (18)
S—C7—N2122.82 (16)C11—C12—H12120.2 (16)
N2—C8—C13122.4 (2)C13—C12—H12120.6 (16)
C9—C8—C13119.9 (2)C8—C13—H13116.2 (14)
N2—C8—C9117.62 (19)C12—C13—H13123.9 (14)
C8—C9—C10120.6 (2)
C7—N1—C6—C149.9 (3)C2—C3—C4—C51.1 (3)
C7—N1—C6—C5134.1 (2)C3—C4—C5—C60.3 (3)
C6—N1—C7—S0.0 (3)C4—C5—C6—N1176.8 (2)
C6—N1—C7—N2177.7 (2)C4—C5—C6—C10.6 (3)
C8—N2—C7—S6.1 (3)N2—C8—C9—C10177.7 (2)
C8—N2—C7—N1171.7 (2)C13—C8—C9—C100.7 (3)
C7—N2—C8—C9124.7 (2)N2—C8—C13—C12178.4 (2)
C7—N2—C8—C1358.4 (3)C9—C8—C13—C121.5 (3)
C6—C1—C2—C30.0 (3)C8—C9—C10—C110.6 (3)
C2—C1—C6—N1176.8 (2)C9—C10—C11—Br2177.91 (16)
C2—C1—C6—C50.8 (3)C9—C10—C11—C121.0 (3)
C1—C2—C3—Br1179.19 (16)Br2—C11—C12—C13178.72 (16)
C1—C2—C3—C40.9 (3)C10—C11—C12—C130.2 (3)
Br1—C3—C4—C5179.05 (16)C11—C12—C13—C81.1 (3)
Symmetry codes: (i) x1, y+1/2, z+1/2; (ii) x+1, y+1/2, z1/2; (iii) x, y1/2, z+1/2; (iv) x+1, y1/2, z+1/2; (v) x+1, y, z; (vi) x, y+1/2, z+1/2; (vii) x, y, z+1; (viii) x, y+1/2, z+1/2; (ix) x, y+1/2, z1/2; (x) x+1, y+1/2, z+1/2; (xi) x, y+1, z+1; (xii) x1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H21···Sviii0.79 (2)2.61 (2)3.355 (2)158 (2)
N2—H22···Sviii0.79 (3)2.53 (3)3.316 (2)168 (3)
C1—H1···S0.97 (2)2.83 (2)3.239 (2)106.2 (15)
C9—H9···Six0.95 (2)2.83 (2)3.510 (2)129.7 (18)
Symmetry codes: (viii) x, y+1/2, z+1/2; (ix) x, y+1/2, z1/2.
 

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