The two bromophenyl rings in the title compound, C
13H
10Br
2N
2S, adopt a
cis–
cis configuration to S with respect to the C—N thiourea bonds. The crystal packing is characterized by N—H
S hydrogen bonds.
Supporting information
CCDC reference: 638521
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.003 Å
- R factor = 0.028
- wR factor = 0.072
- Data-to-parameter ratio = 16.3
checkCIF/PLATON results
No syntax errors found
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
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.
Crystal data top
C13H10Br2N2S | F(000) = 752 |
Mr = 386.11 | The 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/c | Dx = 1.887 Mg m−3 |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 14.077 (1) Å | Cell parameters from 5020 reflections |
b = 7.0804 (6) Å | θ = 2.9–29.4° |
c = 14.054 (1) Å | µ = 6.10 mm−1 |
β = 104.026 (1)° | T = 100 K |
V = 1359.01 (18) Å3 | Block, colorless |
Z = 4 | 0.46 × 0.42 × 0.37 mm |
Data collection top
Bruker SMART Apex diffractometer | 3318 independent reflections |
Radiation source: fine focus sealed Siemens Mo tube | 2769 reflections with I > 2σ(I) |
Parallel mounted graphite monochromator | Rint = 0.029 |
Detector resolution: 4096x4096 / 62x62 (binned 512) pixels mm-1 | θmax = 28.3°, θmin = 3.0° |
φ and ω scans | h = −18→18 |
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) | k = −9→9 |
Tmin = 0.073, Tmax = 0.106 | l = −15→18 |
10894 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: heavy-atom method |
Least-squares matrix: full | Secondary atom site location: structure-invariant direct methods |
R[F2 > 2σ(F2)] = 0.028 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.072 | All 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 parameters | Δρmax = 0.95 e Å−3 |
0 restraints | Δρmin = −0.42 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
Br1 | −0.36823 (2) | 0.19030 (3) | 0.51761 (2) | 0.0285 (1) | |
Br2 | 0.46781 (2) | 0.19606 (3) | 0.16394 (2) | 0.0269 (1) | |
S | 0.08535 (4) | 0.15939 (7) | 0.39401 (4) | 0.0150 (1) | |
N1 | −0.04879 (13) | 0.4225 (3) | 0.31854 (13) | 0.0157 (5) | |
N2 | 0.09041 (13) | 0.4346 (3) | 0.26553 (13) | 0.0165 (5) | |
C1 | −0.09820 (16) | 0.3287 (3) | 0.46781 (17) | 0.0168 (6) | |
C2 | −0.17251 (16) | 0.2784 (3) | 0.51259 (18) | 0.0185 (6) | |
C3 | −0.26763 (16) | 0.2620 (3) | 0.45654 (18) | 0.0190 (6) | |
C4 | −0.29103 (17) | 0.2971 (3) | 0.35681 (18) | 0.0205 (6) | |
C5 | −0.21641 (16) | 0.3469 (3) | 0.31242 (17) | 0.0175 (6) | |
C6 | −0.12027 (15) | 0.3619 (3) | 0.36726 (16) | 0.0149 (6) | |
C7 | 0.04089 (14) | 0.3482 (3) | 0.32398 (15) | 0.0138 (6) | |
C8 | 0.18026 (14) | 0.3759 (3) | 0.24581 (16) | 0.0157 (6) | |
C9 | 0.18244 (15) | 0.3507 (3) | 0.14874 (16) | 0.0153 (5) | |
C10 | 0.26821 (16) | 0.3002 (3) | 0.12420 (18) | 0.0181 (6) | |
C11 | 0.35179 (15) | 0.2735 (3) | 0.19824 (17) | 0.0185 (6) | |
C12 | 0.35166 (17) | 0.2991 (3) | 0.29596 (18) | 0.0207 (6) | |
C13 | 0.26545 (16) | 0.3522 (3) | 0.31977 (17) | 0.0188 (6) | |
H1 | −0.0312 (16) | 0.340 (3) | 0.5055 (17) | 0.008 (5)* | |
H2 | −0.1601 (18) | 0.251 (3) | 0.5822 (18) | 0.017 (6)* | |
H4 | −0.356 (2) | 0.286 (3) | 0.319 (2) | 0.028 (7)* | |
H5 | −0.2302 (16) | 0.377 (3) | 0.2480 (18) | 0.015 (6)* | |
H9 | 0.1236 (17) | 0.374 (3) | 0.1001 (17) | 0.015 (6)* | |
H10 | 0.272 (2) | 0.287 (4) | 0.060 (2) | 0.027 (7)* | |
H12 | 0.411 (2) | 0.285 (3) | 0.346 (2) | 0.026 (7)* | |
H13 | 0.2597 (17) | 0.378 (3) | 0.3902 (19) | 0.022 (6)* | |
H21 | −0.0697 (16) | 0.492 (3) | 0.2746 (18) | 0.017 (6)* | |
H22 | 0.055 (2) | 0.495 (4) | 0.224 (2) | 0.036 (8)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.0248 (1) | 0.0338 (2) | 0.0324 (2) | −0.0052 (1) | 0.0178 (1) | −0.0010 (1) |
Br2 | 0.0177 (1) | 0.0320 (1) | 0.0337 (2) | 0.0020 (1) | 0.0117 (1) | −0.0026 (1) |
S | 0.0178 (2) | 0.0136 (2) | 0.0137 (3) | 0.0010 (2) | 0.0038 (2) | 0.0013 (2) |
N1 | 0.0190 (8) | 0.0143 (8) | 0.0146 (9) | 0.0038 (7) | 0.0058 (7) | 0.0054 (7) |
N2 | 0.0183 (8) | 0.0165 (9) | 0.0160 (10) | 0.0027 (7) | 0.0068 (7) | 0.0046 (7) |
C1 | 0.0208 (10) | 0.0130 (9) | 0.0174 (11) | −0.0002 (8) | 0.0065 (9) | −0.0008 (8) |
C2 | 0.0232 (11) | 0.0163 (10) | 0.0181 (12) | 0.0006 (8) | 0.0092 (9) | 0.0001 (9) |
C3 | 0.0210 (10) | 0.0149 (9) | 0.0257 (12) | −0.0003 (8) | 0.0145 (9) | −0.0017 (9) |
C4 | 0.0173 (10) | 0.0212 (11) | 0.0232 (12) | 0.0006 (8) | 0.0052 (9) | −0.0014 (9) |
C5 | 0.0217 (10) | 0.0165 (10) | 0.0151 (11) | 0.0027 (8) | 0.0058 (9) | 0.0011 (8) |
C6 | 0.0186 (10) | 0.0110 (9) | 0.0176 (11) | 0.0020 (8) | 0.0094 (8) | −0.0009 (8) |
C7 | 0.0184 (10) | 0.0126 (9) | 0.0102 (10) | −0.0016 (7) | 0.0030 (8) | −0.0037 (7) |
C8 | 0.0165 (9) | 0.0128 (9) | 0.0189 (11) | −0.0001 (8) | 0.0065 (8) | 0.0012 (8) |
C9 | 0.0156 (9) | 0.0148 (9) | 0.0148 (10) | −0.0006 (8) | 0.0022 (8) | 0.0017 (8) |
C10 | 0.0214 (10) | 0.0178 (10) | 0.0166 (12) | −0.0031 (8) | 0.0077 (9) | −0.0016 (8) |
C11 | 0.0144 (9) | 0.0157 (10) | 0.0274 (13) | −0.0012 (8) | 0.0092 (9) | −0.0001 (9) |
C12 | 0.0186 (10) | 0.0249 (11) | 0.0181 (12) | −0.0025 (8) | 0.0034 (9) | 0.0016 (9) |
C13 | 0.0205 (10) | 0.0209 (10) | 0.0156 (11) | −0.0025 (8) | 0.0055 (9) | 0.0005 (9) |
Geometric parameters (Å, º) top
Br1—C3 | 1.895 (2) | C8—C13 | 1.394 (3) |
Br2—C11 | 1.893 (2) | C8—C9 | 1.384 (3) |
S—C7 | 1.688 (2) | C9—C10 | 1.381 (3) |
N1—C6 | 1.414 (3) | C10—C11 | 1.382 (3) |
N1—C7 | 1.353 (3) | C11—C12 | 1.386 (3) |
N2—C7 | 1.346 (3) | C12—C13 | 1.387 (3) |
N2—C8 | 1.421 (3) | C1—H1 | 0.97 (2) |
N1—H21 | 0.79 (2) | C2—H2 | 0.97 (2) |
N2—H22 | 0.79 (3) | C4—H4 | 0.94 (3) |
C1—C6 | 1.391 (3) | C5—H5 | 0.90 (2) |
C1—C2 | 1.392 (3) | C9—H9 | 0.95 (2) |
C2—C3 | 1.384 (3) | C10—H10 | 0.92 (3) |
C3—C4 | 1.382 (3) | C12—H12 | 0.96 (3) |
C4—C5 | 1.391 (3) | C13—H13 | 1.03 (3) |
C5—C6 | 1.390 (3) | | |
| | | |
Br1···Br2i | 3.5362 (5) | C9···C4viii | 3.520 (3) |
Br2···Br1ii | 3.5362 (5) | C9···C5viii | 3.570 (3) |
Br2···C4iii | 3.729 (2) | C10···Six | 3.625 (3) |
Br2···C12iv | 3.739 (2) | C10···C3viii | 3.460 (3) |
Br2···H4v | 2.95 (3) | C10···C4iii | 3.581 (3) |
S···C1 | 3.239 (2) | C10···C4viii | 3.537 (3) |
S···C13 | 3.265 (2) | C10···C5iii | 3.456 (3) |
S···N2iii | 3.316 (2) | C11···C5iii | 3.555 (3) |
S···C9vi | 3.510 (2) | C11···C4iii | 3.520 (3) |
S···N1iii | 3.355 (2) | C12···Br2x | 3.739 (2) |
S···C2vii | 3.472 (2) | C13···S | 3.265 (2) |
S···C10vi | 3.625 (3) | C1···H1xi | 2.94 (2) |
S···H21iii | 2.61 (2) | C7···H22iii | 2.84 (3) |
S···H22iii | 2.53 (3) | C7···H1 | 2.97 (2) |
S···H2vii | 3.08 (2) | C7···H13 | 3.00 (3) |
S···H13 | 2.91 (2) | C7···H21iii | 2.95 (2) |
S···H1 | 2.83 (2) | H1···S | 2.83 (2) |
S···H9vi | 2.83 (2) | H1···C7 | 2.97 (2) |
S···H10vi | 3.09 (3) | H1···C1xi | 2.94 (2) |
N1···Sviii | 3.355 (2) | H1···H1xi | 2.45 (3) |
N2···Sviii | 3.316 (2) | H2···Svii | 3.08 (2) |
C1···S | 3.239 (2) | H4···Br2xii | 2.95 (3) |
C2···Svii | 3.472 (2) | H5···H21 | 2.35 (3) |
C3···C10iii | 3.460 (3) | H9···H22 | 2.35 (4) |
C4···C11viii | 3.520 (3) | H9···Six | 2.83 (2) |
C4···Br2viii | 3.729 (2) | H10···Six | 3.09 (3) |
C4···C9iii | 3.520 (3) | H13···S | 2.91 (2) |
C4···C10iii | 3.537 (3) | H13···C7 | 3.00 (3) |
C4···C10viii | 3.581 (3) | H21···H5 | 2.35 (3) |
C5···C10viii | 3.456 (3) | H21···H22 | 2.05 (4) |
C5···C8iii | 3.500 (3) | H21···Sviii | 2.61 (2) |
C5···C9iii | 3.570 (3) | H21···C7viii | 2.95 (2) |
C5···C11viii | 3.555 (3) | H22···H9 | 2.35 (4) |
C6···C9viii | 3.564 (3) | H22···H21 | 2.05 (4) |
C8···C5viii | 3.500 (3) | H22···Sviii | 2.53 (3) |
C9···Six | 3.510 (2) | H22···C7viii | 2.84 (3) |
C9···C6iii | 3.564 (3) | | |
| | | |
C6—N1—C7 | 128.21 (19) | C9—C10—C11 | 118.9 (2) |
C7—N2—C8 | 127.1 (2) | Br2—C11—C10 | 118.53 (17) |
C6—N1—H21 | 113.2 (17) | C10—C11—C12 | 121.5 (2) |
C7—N1—H21 | 116.9 (17) | Br2—C11—C12 | 119.92 (17) |
C7—N2—H22 | 112 (2) | C11—C12—C13 | 119.1 (2) |
C8—N2—H22 | 116 (2) | C8—C13—C12 | 119.9 (2) |
C2—C1—C6 | 119.7 (2) | C2—C1—H1 | 120.9 (14) |
C1—C2—C3 | 119.6 (2) | C6—C1—H1 | 119.4 (14) |
Br1—C3—C2 | 119.40 (18) | C1—C2—H2 | 122.4 (16) |
Br1—C3—C4 | 119.14 (18) | C3—C2—H2 | 118.0 (15) |
C2—C3—C4 | 121.5 (2) | C3—C4—H4 | 121.1 (17) |
C3—C4—C5 | 118.7 (2) | C5—C4—H4 | 120.2 (17) |
C4—C5—C6 | 120.7 (2) | C4—C5—H5 | 120.4 (15) |
N1—C6—C1 | 122.2 (2) | C6—C5—H5 | 118.8 (15) |
N1—C6—C5 | 117.79 (19) | C8—C9—H9 | 117.5 (15) |
C1—C6—C5 | 119.9 (2) | C10—C9—H9 | 121.8 (15) |
N1—C7—N2 | 113.76 (19) | C9—C10—H10 | 122.2 (18) |
S—C7—N1 | 123.37 (16) | C11—C10—H10 | 118.9 (18) |
S—C7—N2 | 122.82 (16) | C11—C12—H12 | 120.2 (16) |
N2—C8—C13 | 122.4 (2) | C13—C12—H12 | 120.6 (16) |
C9—C8—C13 | 119.9 (2) | C8—C13—H13 | 116.2 (14) |
N2—C8—C9 | 117.62 (19) | C12—C13—H13 | 123.9 (14) |
C8—C9—C10 | 120.6 (2) | | |
| | | |
C7—N1—C6—C1 | 49.9 (3) | C2—C3—C4—C5 | 1.1 (3) |
C7—N1—C6—C5 | −134.1 (2) | C3—C4—C5—C6 | −0.3 (3) |
C6—N1—C7—S | 0.0 (3) | C4—C5—C6—N1 | −176.8 (2) |
C6—N1—C7—N2 | 177.7 (2) | C4—C5—C6—C1 | −0.6 (3) |
C8—N2—C7—S | 6.1 (3) | N2—C8—C9—C10 | 177.7 (2) |
C8—N2—C7—N1 | −171.7 (2) | C13—C8—C9—C10 | 0.7 (3) |
C7—N2—C8—C9 | 124.7 (2) | N2—C8—C13—C12 | −178.4 (2) |
C7—N2—C8—C13 | −58.4 (3) | C9—C8—C13—C12 | −1.5 (3) |
C6—C1—C2—C3 | 0.0 (3) | C8—C9—C10—C11 | 0.6 (3) |
C2—C1—C6—N1 | 176.8 (2) | C9—C10—C11—Br2 | 177.91 (16) |
C2—C1—C6—C5 | 0.8 (3) | C9—C10—C11—C12 | −1.0 (3) |
C1—C2—C3—Br1 | 179.19 (16) | Br2—C11—C12—C13 | −178.72 (16) |
C1—C2—C3—C4 | −0.9 (3) | C10—C11—C12—C13 | 0.2 (3) |
Br1—C3—C4—C5 | −179.05 (16) | C11—C12—C13—C8 | 1.1 (3) |
Symmetry codes: (i) x−1, −y+1/2, z+1/2; (ii) x+1, −y+1/2, z−1/2; (iii) −x, y−1/2, −z+1/2; (iv) −x+1, y−1/2, −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, z−1/2; (x) −x+1, y+1/2, −z+1/2; (xi) −x, −y+1, −z+1; (xii) x−1, y, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H21···Sviii | 0.79 (2) | 2.61 (2) | 3.355 (2) | 158 (2) |
N2—H22···Sviii | 0.79 (3) | 2.53 (3) | 3.316 (2) | 168 (3) |
C1—H1···S | 0.97 (2) | 2.83 (2) | 3.239 (2) | 106.2 (15) |
C9—H9···Six | 0.95 (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, z−1/2. |