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Acta Cryst. (2011). E67, o46    [ doi:10.1107/S1600536810050373 ]

1-(4-Bromophenyl)-3-butanoylthiourea

S. Saeed, N. Rashid, J. P. Jasinski, R. J. Butcher and M. Shoaib

Abstract top

In the title compound, C11H13BrN2OS, there are two independent molecules (A and B) in the asymmetric unit. The dihedral angle between the mean planes of the benzene ring and the carbamothioyl group is 63.66 (molecule A) and 80.3 (0)° (molecule B). The butanamide group in molecule A is disordered [0.532 (6) and 0.468 (6) occupancy]. The carbamothioyl group is twisted by 63.6 (6) (molecule A) and 80.3 (0)° (molecule B) from the respective benzene ring. A strong intramolecular N-H...O hydrogen bond occurs in each molecule. The crystal packing is stabilized by weak intermolecular N-H...O and N-H...S hydrogen-bond interactions, the latter forming an infinite co-operative hydrogen-bonded two-dimensional network along [110].

Comment top

The background to this study has been set in our previous work on the structural chemistry of N, N'-disubstituted thiourea (Saeed et al., 2008a,b). Herein, as a continuation of these studies, the structure of the title compound, (I), C11H13BrN2OS, is described. With two molecules in the asymmetric unit, the dihedral angle between the mean planes of the benzene ring and carbamothioyl group is 63.66° (A) Fig. 1) and 80.3 (0)° (B) (Fig. 2), respectively. The butanamide group in A is disordered (0.532 (6) & 0.4686 occupancy). The carbamothioyl group is twisted by 63.6 (6)° (A) and 80.3 (0)° (B) from the mean plane of the respective benzene ring. Bond distances and angles are in normal ranges (Allen et al. , 1987). Crystal packing is stabilized by strong intramolecular N—H···O and weak intermolecular N—H···O and N—H···S hydrogen bond interactions, the latter forming an infinite cooperative hydrogen bonded 2-D network along 110. (Fig. 3).

Related literature top

For general background to the chemistry of thiourea derivatives, see: Zhang et al. (2004); For related structures, see: Saeed et al. (2008a,b, 2009). For an epoxy resin curing agent, see: Saeed et al. (2009). For bond-length data, see: Allen et al. (1987).

Experimental top

A solution of butanoyl chloride (0.01 mol) in anhydrous acetone (75 ml) and 3% tetrabutylammonium bromide (TBAB) as a phase-transfer catalyst (PTC) in anhydrous acetone was added dropwise to a suspension of dry potassium thiocyanate (0.01 mol) in acetone (50 ml) and the reaction mixture was refluxed for 50 min. After cooling to room temperature, a solution of p-bromoaniline (0.01 mol) in anhydrous acetone (25 ml) was added dropwise and the resulting mixture refluxed for 3 h. Hydrochloric acid (0.1 N, 300 ml) was added, and the solution was filtered. The solid product was washed with water and purified by re-crystallization from ethyl acetate (yield: 92%).

Refinement top

N-H bond lengths were set to 0.88Å. All other H atoms were placed in calculated positions and then refined using the riding model approximation with atom–H lengths of 0.95 Å (CH), 0.99 Å (CH2), or 0.98 Å (CH3). Isotropic displacement parameters for these atoms were set to 1.2 (CH, CH2, NH) or 1.50 (CH3) times Ueq of the parent atom.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. Molecular structure of C11H13BrN2OS, (A) showing the atom labeling scheme and 50% probability displacement ellipsoids. Dashed lined indicate intramolecular N—H···O hydrogen bonding. Only the predominate butanamide component (0.532 (6) occupancy) is displayed.
[Figure 2] Fig. 2. Molecular structure of C11H13BrN2OS, (B) showing the atom labeling scheme and 50% probability displacement ellipsoids. Dashed lined indicate intramolecular N—H···O hydrogen bonding.
[Figure 3] Fig. 3. Packing diagram of the title compound viewed down the c axis. Dashed lines indicate strong N—H···O, weak N—H···O and N—H···S hydrogen bonds and are also displaying an R22(8) graph set motif betwen adjacent A–B molecules.
1-(4-Bromophenyl)-3-butanoylthiourea top
Crystal data top
C11H13BrN2OSZ = 4
Mr = 301.20F(000) = 608
Triclinic, P1Dx = 1.593 Mg m−3
Hall symbol: -P 1Melting point: 409 K
a = 6.1746 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.7883 (4) ÅCell parameters from 6019 reflections
c = 19.6450 (8) Åθ = 5.1–28.4°
α = 87.719 (3)°µ = 3.42 mm−1
β = 81.557 (4)°T = 123 K
γ = 76.047 (4)°Prism, colorless
V = 1256.23 (9) Å30.53 × 0.24 × 0.11 mm
Data collection top
Oxford Diffraction Xcalibur Ruby Gemini
diffractometer		5362 independent reflections
Radiation source: Enhance (Mo) X-ray Source3535 reflections with I > 2σ(I)
graphiteRint = 0.054
Detector resolution: 10.5081 pixels mm-1θmax = 28.5°, θmin = 5.1°
ω scansh = −8→8
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2007)		k = −13→14
Tmin = 0.187, Tmax = 1.000l = −24→26
13276 measured reflections
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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095H-atom parameters constrained
S = 0.92 w = 1/[σ2(Fo2) + (0.0504P)2]
where P = (Fo2 + 2Fc2)/3
5362 reflections(Δ/σ)max = 0.001
307 parametersΔρmax = 0.83 e Å−3
18 restraintsΔρmin = −0.74 e Å−3
Crystal data top
C11H13BrN2OSγ = 76.047 (4)°
Mr = 301.20V = 1256.23 (9) Å3
Triclinic, P1Z = 4
a = 6.1746 (3) ÅMo Kα radiation
b = 10.7883 (4) ŵ = 3.42 mm−1
c = 19.6450 (8) ÅT = 123 K
α = 87.719 (3)°0.53 × 0.24 × 0.11 mm
β = 81.557 (4)°
Data collection top
Oxford Diffraction Xcalibur Ruby Gemini
diffractometer		5362 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2007)		3535 reflections with I > 2σ(I)
Tmin = 0.187, Tmax = 1.000Rint = 0.054
13276 measured reflectionsθmax = 28.5°
Refinement top
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.095Δρmax = 0.83 e Å−3
S = 0.92Δρmin = −0.74 e Å−3
5362 reflectionsAbsolute structure: ?
307 parametersFlack parameter: ?
18 restraintsRogers parameter: ?
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*/UeqOcc. (<1)
Br1A1.12197 (6)0.33692 (3)0.30413 (2)0.02775 (12)
S1A0.6977 (2)0.04500 (13)0.07060 (6)0.0486 (3)
O1A0.3799 (6)0.4183 (4)−0.03038 (17)0.0751 (13)
N1A0.6368 (5)0.2974 (4)0.06119 (16)0.0360 (8)
H1AA0.58350.36900.03980.043*
N2A0.4761 (6)0.2029 (4)−0.01539 (17)0.0454 (10)0.468 (6)
H2AB0.46920.1311−0.03370.054*0.468 (6)
N2C0.4761 (6)0.2029 (4)−0.01539 (17)0.0454 (10)0.532 (6)
H2CA0.45770.1312−0.03080.054*0.532 (6)
C1A0.7542 (6)0.3041 (4)0.11839 (19)0.0267 (9)
C2A0.9809 (6)0.2465 (4)0.11540 (19)0.0276 (9)
H2AA1.06080.19970.07580.033*
C3A1.0908 (6)0.2578 (4)0.17075 (19)0.0256 (9)
H3AA1.24700.21950.16940.031*
C4A0.9692 (6)0.3256 (3)0.22803 (19)0.0239 (8)
C5A0.7432 (6)0.3813 (3)0.23116 (19)0.0252 (9)
H5AA0.66210.42710.27100.030*
C6A0.6355 (6)0.3701 (3)0.1759 (2)0.0264 (9)
H6AA0.47910.40800.17750.032*
C7A0.6030 (6)0.1894 (5)0.0382 (2)0.0380 (11)
C8A0.359 (8)0.3127 (6)−0.044 (2)0.066 (3)0.468 (6)
C9A0.1864 (14)0.2620 (8)−0.0861 (4)0.0248 (13)0.468 (6)
H9AA0.27270.2012−0.12250.030*0.468 (6)
H9AB0.08920.2179−0.05430.030*0.468 (6)
C10A0.047 (4)0.375 (3)−0.1171 (9)0.045 (3)0.468 (6)
H10A0.14730.4270−0.14150.054*0.468 (6)
H10B−0.05410.4286−0.07990.054*0.468 (6)
C11A−0.095 (6)0.340 (4)−0.1676 (15)0.044 (5)0.468 (6)
H11A−0.15110.4151−0.19540.066*0.468 (6)
H11B−0.22210.3113−0.14190.066*0.468 (6)
H11C−0.00140.2714−0.19770.066*0.468 (6)
C8C0.375 (7)0.3120 (5)−0.0481 (19)0.066 (3)0.532 (6)
C9C0.2633 (12)0.3155 (7)−0.1089 (4)0.0248 (13)0.532 (6)
H9CA0.29770.2288−0.12870.030*0.532 (6)
H9CB0.32000.3727−0.14410.030*0.532 (6)
C10C0.008 (4)0.364 (2)−0.0892 (8)0.045 (3)0.532 (6)
H10C−0.04070.3218−0.04600.054*0.532 (6)
H10D−0.02800.4570−0.08090.054*0.532 (6)
C11C−0.119 (5)0.338 (3)−0.1444 (11)0.044 (5)0.532 (6)
H11D−0.27940.3790−0.13250.066*0.532 (6)
H11E−0.10060.2454−0.14840.066*0.532 (6)
H11F−0.06040.3718−0.18850.066*0.532 (6)
Br1B0.29893 (6)−0.08278 (4)0.22800 (2)0.03337 (13)
S1B0.40894 (16)0.38143 (8)0.43013 (5)0.0282 (2)
O1B0.9939 (4)0.1368 (2)0.52752 (12)0.0214 (5)
N1B0.7056 (5)0.1586 (3)0.43688 (15)0.0199 (7)
H1BA0.82140.11060.45430.024*
N2B0.7405 (5)0.3202 (3)0.50548 (14)0.0214 (7)
H2BB0.69380.40150.51660.026*
C1B0.6082 (5)0.1031 (3)0.38714 (17)0.0170 (8)
C2B0.7103 (6)0.0919 (3)0.31965 (18)0.0199 (8)
H2BA0.84300.12170.30620.024*
C3B0.6197 (6)0.0373 (3)0.27136 (19)0.0223 (8)
H3BA0.68850.02970.22470.027*
C4B0.4275 (6)−0.0060 (3)0.29247 (19)0.0214 (8)
C5B0.3250 (6)0.0038 (3)0.35972 (19)0.0222 (8)
H5BA0.1928−0.02660.37320.027*
C6B0.4171 (6)0.0584 (3)0.40740 (19)0.0217 (8)
H6BA0.34890.06520.45410.026*
C7B0.6293 (6)0.2788 (3)0.45781 (17)0.0196 (8)
C8B0.9147 (5)0.2507 (3)0.53771 (17)0.0188 (8)
C9B0.9965 (6)0.3278 (3)0.58645 (19)0.0227 (8)
H9BA0.87480.35700.62520.027*
H9BB1.03030.40450.56200.027*
C10B1.2057 (6)0.2531 (3)0.6150 (2)0.0286 (9)
H10E1.32260.21620.57630.034*
H10F1.16800.18170.64370.034*
C11B1.2993 (7)0.3366 (4)0.6579 (2)0.0366 (10)
H11G1.43830.28620.67320.055*
H11H1.18810.36820.69810.055*
H11I1.33190.40900.63010.055*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br1A0.0310 (2)0.0221 (2)0.0329 (2)−0.00409 (16)−0.01694 (17)−0.00039 (17)
S1A0.0591 (8)0.0681 (8)0.0314 (6)−0.0304 (7)−0.0239 (5)0.0060 (6)
O1A0.079 (3)0.080 (3)0.047 (2)0.038 (2)−0.039 (2)−0.024 (2)
N1A0.0339 (19)0.055 (2)0.0200 (18)−0.0100 (17)−0.0101 (15)0.0062 (17)
N2A0.033 (2)0.071 (3)0.026 (2)0.0062 (19)−0.0118 (16)−0.0179 (19)
N2C0.033 (2)0.071 (3)0.026 (2)0.0062 (19)−0.0118 (16)−0.0179 (19)
C1A0.030 (2)0.035 (2)0.017 (2)−0.0117 (18)−0.0078 (16)0.0106 (17)
C2A0.028 (2)0.038 (2)0.018 (2)−0.0102 (18)−0.0037 (16)0.0027 (18)
C3A0.0193 (19)0.030 (2)0.029 (2)−0.0085 (17)−0.0036 (16)0.0036 (18)
C4A0.030 (2)0.0193 (19)0.029 (2)−0.0116 (17)−0.0162 (17)0.0082 (16)
C5A0.027 (2)0.0217 (19)0.028 (2)−0.0061 (17)−0.0066 (17)−0.0009 (16)
C6A0.021 (2)0.025 (2)0.034 (2)−0.0037 (16)−0.0096 (17)0.0024 (18)
C7A0.024 (2)0.070 (3)0.020 (2)−0.010 (2)−0.0043 (17)−0.003 (2)
C8A0.050 (5)0.091 (4)0.038 (4)0.037 (3)−0.022 (4)−0.034 (3)
C9A0.032 (4)0.025 (3)0.022 (3)−0.014 (2)−0.007 (3)−0.002 (3)
C10A0.033 (8)0.056 (6)0.049 (11)−0.013 (4)−0.010 (8)−0.004 (10)
C11A0.036 (6)0.049 (3)0.055 (15)−0.014 (4)−0.024 (9)0.009 (10)
C8C0.050 (5)0.091 (4)0.038 (4)0.037 (3)−0.022 (4)−0.034 (3)
C9C0.032 (4)0.025 (3)0.022 (3)−0.014 (2)−0.007 (3)−0.002 (3)
C10C0.033 (8)0.056 (6)0.049 (11)−0.013 (4)−0.010 (8)−0.004 (10)
C11C0.036 (6)0.049 (3)0.055 (15)−0.014 (4)−0.024 (9)0.009 (10)
Br1B0.0354 (2)0.0344 (2)0.0352 (3)−0.01105 (19)−0.01454 (18)−0.00672 (19)
S1B0.0362 (6)0.0152 (5)0.0327 (6)0.0040 (4)−0.0195 (4)−0.0041 (4)
O1B0.0235 (13)0.0133 (12)0.0262 (14)−0.0003 (11)−0.0065 (11)−0.0011 (11)
N1B0.0211 (15)0.0125 (15)0.0247 (17)0.0024 (12)−0.0080 (13)−0.0045 (13)
N2B0.0286 (17)0.0113 (14)0.0233 (17)0.0020 (13)−0.0105 (13)−0.0025 (13)
C1B0.0212 (18)0.0084 (16)0.021 (2)0.0001 (14)−0.0076 (15)0.0001 (14)
C2B0.0202 (18)0.0138 (17)0.026 (2)−0.0039 (15)−0.0037 (15)0.0014 (15)
C3B0.026 (2)0.0197 (19)0.0192 (19)−0.0004 (16)−0.0036 (15)−0.0008 (15)
C4B0.027 (2)0.0111 (17)0.028 (2)−0.0042 (15)−0.0118 (16)−0.0013 (15)
C5B0.0173 (18)0.0152 (18)0.033 (2)−0.0018 (15)−0.0053 (16)0.0019 (16)
C6B0.0193 (19)0.0188 (18)0.023 (2)0.0026 (15)−0.0012 (15)−0.0010 (16)
C7B0.026 (2)0.0151 (18)0.0185 (19)−0.0039 (16)−0.0065 (16)0.0019 (15)
C8B0.0199 (18)0.0179 (18)0.0180 (19)−0.0033 (16)−0.0037 (15)0.0029 (15)
C9B0.0237 (19)0.0149 (18)0.028 (2)0.0022 (15)−0.0087 (16)−0.0027 (15)
C10B0.030 (2)0.0149 (19)0.041 (2)0.0011 (16)−0.0171 (18)−0.0005 (17)
C11B0.031 (2)0.023 (2)0.058 (3)−0.0008 (18)−0.022 (2)−0.005 (2)
Geometric parameters (Å, °) top
Br1A—C4A1.904 (3)C10C—H10C0.9900
S1A—C7A1.663 (5)C10C—H10D0.9900
O1A—C8C1.220 (4)C11C—H11D0.9800
O1A—C8A1.220 (4)C11C—H11E0.9800
N1A—C7A1.338 (5)C11C—H11F0.9800
N1A—C1A1.437 (4)Br1B—C4B1.902 (3)
N1A—H1AA0.8800S1B—C7B1.678 (3)
N2A—C8A1.376 (4)O1B—C8B1.221 (3)
N2A—C7A1.385 (5)N1B—C7B1.328 (4)
N2A—H2AB0.8800N1B—C1B1.438 (4)
C1A—C6A1.374 (5)N1B—H1BA0.8800
C1A—C2A1.382 (5)N2B—C8B1.376 (4)
C2A—C3A1.387 (5)N2B—C7B1.386 (4)
C2A—H2AA0.9500N2B—H2BB0.8800
C3A—C4A1.385 (5)C1B—C2B1.378 (5)
C3A—H3AA0.9500C1B—C6B1.380 (5)
C4A—C5A1.373 (5)C2B—C3B1.385 (5)
C5A—C6A1.377 (5)C2B—H2BA0.9500
C5A—H5AA0.9500C3B—C4B1.381 (5)
C6A—H6AA0.9500C3B—H3BA0.9500
C8A—C9A1.644 (14)C4B—C5B1.375 (5)
C9A—C10A1.48 (3)C5B—C6B1.382 (5)
C9A—H9AA0.9900C5B—H5BA0.9500
C9A—H9AB0.9900C6B—H6BA0.9500
C10A—C11A1.53 (5)C8B—C9B1.508 (4)
C10A—H10A0.9900C9B—C10B1.518 (5)
C10A—H10B0.9900C9B—H9BA0.9900
C11A—H11A0.9800C9B—H9BB0.9900
C11A—H11B0.9800C10B—C11B1.521 (5)
C11A—H11C0.9800C10B—H10E0.9900
C8C—C9C1.459 (11)C10B—H10F0.9900
C9C—C10C1.53 (2)C11B—H11G0.9800
C9C—H9CA0.9900C11B—H11H0.9800
C9C—H9CB0.9900C11B—H11I0.9800
C10C—C11C1.50 (4)
C8C—O1A—C8A5(6)H10C—C10C—H10D107.9
C7A—N1A—C1A124.4 (4)C10C—C11C—H11D109.5
C7A—N1A—H1AA117.8C10C—C11C—H11E109.5
C1A—N1A—H1AA117.8H11D—C11C—H11E109.5
C8A—N2A—C7A129.2 (5)C10C—C11C—H11F109.5
C8A—N2A—H2AB115.4H11D—C11C—H11F109.5
C7A—N2A—H2AB115.4H11E—C11C—H11F109.5
C6A—C1A—C2A120.9 (3)C7B—N1B—C1B123.1 (3)
C6A—C1A—N1A118.3 (3)C7B—N1B—H1BA118.4
C2A—C1A—N1A120.8 (3)C1B—N1B—H1BA118.4
C1A—C2A—C3A119.4 (3)C8B—N2B—C7B128.4 (3)
C1A—C2A—H2AA120.3C8B—N2B—H2BB115.8
C3A—C2A—H2AA120.3C7B—N2B—H2BB115.8
C4A—C3A—C2A118.9 (3)C2B—C1B—C6B120.4 (3)
C4A—C3A—H3AA120.5C2B—C1B—N1B119.6 (3)
C2A—C3A—H3AA120.5C6B—C1B—N1B120.0 (3)
C5A—C4A—C3A121.5 (3)C1B—C2B—C3B120.2 (3)
C5A—C4A—Br1A120.3 (3)C1B—C2B—H2BA119.9
C3A—C4A—Br1A118.2 (3)C3B—C2B—H2BA119.9
C4A—C5A—C6A119.2 (3)C4B—C3B—C2B118.6 (3)
C4A—C5A—H5AA120.4C4B—C3B—H3BA120.7
C6A—C5A—H5AA120.4C2B—C3B—H3BA120.7
C1A—C6A—C5A120.0 (3)C5B—C4B—C3B121.8 (3)
C1A—C6A—H6AA120.0C5B—C4B—Br1B118.3 (3)
C5A—C6A—H6AA120.0C3B—C4B—Br1B120.0 (3)
N1A—C7A—N2A116.0 (4)C4B—C5B—C6B119.0 (3)
N1A—C7A—S1A124.5 (3)C4B—C5B—H5BA120.5
N2A—C7A—S1A119.5 (3)C6B—C5B—H5BA120.5
O1A—C8A—N2A122.2 (5)C1B—C6B—C5B120.0 (3)
O1A—C8A—C9A133.9 (10)C1B—C6B—H6BA120.0
N2A—C8A—C9A103.4 (6)C5B—C6B—H6BA120.0
C10A—C9A—C8A107.3 (12)N1B—C7B—N2B117.1 (3)
C10A—C9A—H9AA110.3N1B—C7B—S1B124.1 (3)
C8A—C9A—H9AA110.3N2B—C7B—S1B118.9 (2)
C10A—C9A—H9AB110.3O1B—C8B—N2B122.5 (3)
C8A—C9A—H9AB110.3O1B—C8B—C9B123.6 (3)
H9AA—C9A—H9AB108.5N2B—C8B—C9B113.9 (3)
C9A—C10A—C11A113 (2)C8B—C9B—C10B112.9 (3)
C9A—C10A—H10A109.0C8B—C9B—H9BA109.0
C11A—C10A—H10A109.0C10B—C9B—H9BA109.0
C9A—C10A—H10B109.0C8B—C9B—H9BB109.0
C11A—C10A—H10B109.0C10B—C9B—H9BB109.0
H10A—C10A—H10B107.8H9BA—C9B—H9BB107.8
O1A—C8C—C9C112.4 (6)C9B—C10B—C11B111.9 (3)
C8C—C9C—C10C110 (2)C9B—C10B—H10E109.2
C8C—C9C—H9CA109.7C11B—C10B—H10E109.2
C10C—C9C—H9CA109.7C9B—C10B—H10F109.2
C8C—C9C—H9CB109.7C11B—C10B—H10F109.2
C10C—C9C—H9CB109.7H10E—C10B—H10F107.9
H9CA—C9C—H9CB108.2C10B—C11B—H11G109.5
C11C—C10C—C9C111.9 (16)C10B—C11B—H11H109.5
C11C—C10C—H10C109.2H11G—C11B—H11H109.5
C9C—C10C—H10C109.2C10B—C11B—H11I109.5
C11C—C10C—H10D109.2H11G—C11B—H11I109.5
C9C—C10C—H10D109.2H11H—C11B—H11I109.5
C7A—N1A—C1A—C6A−115.5 (4)O1A—C8C—C9C—C10C−74 (4)
C7A—N1A—C1A—C2A65.0 (5)C8C—C9C—C10C—C11C−165.1 (18)
C6A—C1A—C2A—C3A−1.3 (6)C7B—N1B—C1B—C2B100.1 (4)
N1A—C1A—C2A—C3A178.2 (3)C7B—N1B—C1B—C6B−81.5 (4)
C1A—C2A—C3A—C4A0.7 (5)C6B—C1B—C2B—C3B0.9 (5)
C2A—C3A—C4A—C5A0.2 (5)N1B—C1B—C2B—C3B179.2 (3)
C2A—C3A—C4A—Br1A178.8 (3)C1B—C2B—C3B—C4B−0.4 (5)
C3A—C4A—C5A—C6A−0.4 (6)C2B—C3B—C4B—C5B0.0 (5)
Br1A—C4A—C5A—C6A−179.0 (3)C2B—C3B—C4B—Br1B−179.5 (2)
C2A—C1A—C6A—C5A1.1 (6)C3B—C4B—C5B—C6B0.0 (5)
N1A—C1A—C6A—C5A−178.5 (3)Br1B—C4B—C5B—C6B179.5 (2)
C4A—C5A—C6A—C1A−0.2 (5)C2B—C1B—C6B—C5B−1.0 (5)
C1A—N1A—C7A—N2A176.9 (3)N1B—C1B—C6B—C5B−179.3 (3)
C1A—N1A—C7A—S1A−1.9 (5)C4B—C5B—C6B—C1B0.5 (5)
C8A—N2A—C7A—N1A−8(3)C1B—N1B—C7B—N2B−179.4 (3)
C8A—N2A—C7A—S1A171 (3)C1B—N1B—C7B—S1B0.7 (5)
C8C—O1A—C8A—N2A85 (4)C8B—N2B—C7B—N1B−4.1 (5)
C8C—O1A—C8A—C9A−104 (7)C8B—N2B—C7B—S1B175.8 (3)
C7A—N2A—C8A—O1A11 (7)C7B—N2B—C8B—O1B−0.8 (6)
C7A—N2A—C8A—C9A−162.5 (8)C7B—N2B—C8B—C9B179.5 (3)
O1A—C8A—C9A—C10A6(7)O1B—C8B—C9B—C10B6.9 (5)
N2A—C8A—C9A—C10A178 (3)N2B—C8B—C9B—C10B−173.3 (3)
C8A—C9A—C10A—C11A171 (3)C8B—C9B—C10B—C11B174.0 (3)
C8A—O1A—C8C—C9C98 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1A—H1AA···O1A0.881.972.666 (5)135
N1A—H1AA···O1Ai0.882.363.083 (6)140
N2A—H2AB···S1Aii0.882.543.382 (4)160
N1B—H1BA···O1B0.881.982.662 (4)134
N2B—H2BB···S1Biii0.882.503.370 (3)169
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, −y, −z; (iii) −x+1, −y+1, −z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1A—H1AA···O1A0.881.972.666 (5)135
N1A—H1AA···O1Ai0.882.363.083 (6)140
N2A—H2AB···S1Aii0.882.543.382 (4)160
N1B—H1BA···O1B0.881.982.662 (4)134
N2B—H2BB···S1Biii0.882.503.370 (3)169
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, −y, −z; (iii) −x+1, −y+1, −z+1.
Acknowledgements top

RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase an X-ray diffractometer.

references
References top

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.

Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.

Saeed, S., Bhatti, M. H., Tahir, M. K. & Jones, P. G. (2008a). Acta Cryst. E64, o1369.

Saeed, S., Bhatti, M. H., Yunus, U. & Jones, P. G. (2008b). Acta Cryst. E64, o1566.

Saeed, S., Rashid, N., Tahir, A. & Jones, P. G. (2009). Acta Cryst. E65, o1870–o1871.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Spek, A. L. (2009). Acta Cryst. D65, 148–155.

Zhang, Y.-M., Wei, T.-B., Xian, L. & &Gao, L.-M. (2004). Phosphorus Sulphur Silicon Relat. Elem. 179, 2007–2013.