2-Bromo-N-(dibenzyl-carbamothioyl)benzamide.

The 2-bromo-benzoyl group in the title compound, C(22)H(19)BrN(2)OS, adopts an E conformation with respect to the thiono S atom across the N-C bond. In the crystal structure, the mol-ecule is stablized by N-H⋯O inter-molecular hydrogen bonds, forming a one-dimensional chain along the b axis.

Related literature

For related structures, see: Yamin & Hassan (2004 ▶); Hassan et al. (2008a ▶,b ▶,c ▶, 2009 ▶). For the synthesis, see: Hassan et al. (2008a ▶). For reference bond distances, see: Allen et al. (2004 ▶).

Experimental

Crystal data

C22H19BrN2OS

M = 439.36

Tetragonal,

a = 12.2833 (16) Å

c = 14.002 (4) Å

V = 2112.6 (7) Å3

Z = 4

Mo Kα radiation

μ = 2.06 mm−1

T = 273 K

0.35 × 0.31 × 0.23 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.533, T max = 0.649

15683 measured reflections

5217 independent reflections

2506 reflections with I > 2σ(I)

R int = 0.064

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.118

S = 0.93

5217 reflections

244 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.57 e Å−3

Δρmin = −0.20 e Å−3

Absolute structure: Flack (1983 ▶), with 2474 Friedel pairs

Flack parameter: −0.001 (11)

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶), ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶), PARST (Nardelli, 1995 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811014711/dn2677sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811014711/dn2677Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C22H19BrN2OS	Dx = 1.381 Mg m−3
Mr = 439.36	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P43	Cell parameters from 2531 reflections
Hall symbol: P 4cw	θ = 1.7–28.4°
a = 12.2833 (16) Å	µ = 2.06 mm−1
c = 14.002 (4) Å	T = 273 K
V = 2112.6 (7) Å3	Block, colourless
Z = 4	0.35 × 0.31 × 0.23 mm
F(000) = 896

Bruker SMART APEX CCD area-detector diffractometer	5217 independent reflections
Radiation source: fine-focus sealed tube	2506 reflections with I > 2σ(I)
graphite	Rint = 0.064
ω scans	θmax = 28.4°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −12→16
Tmin = 0.533, Tmax = 0.649	k = −14→16
15683 measured reflections	l = −18→18

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050	H-atom parameters constrained
wR(F2) = 0.118	w = 1/[σ2(Fo2) + (0.0418P)2] where P = (Fo2 + 2Fc2)/3
S = 0.93	(Δ/σ)max < 0.001
5217 reflections	Δρmax = 0.57 e Å−3
244 parameters	Δρmin = −0.20 e Å−3
1 restraint	Absolute structure: Flack (1983), with 2474 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.001 (11)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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.

	x	y	z	Uiso*/Ueq
Br1	0.20156 (4)	0.59332 (4)	0.23207 (5)	0.0975 (2)
S1	0.48743 (15)	0.81061 (10)	−0.01270 (10)	0.1136 (5)
O1	0.5373 (2)	0.6765 (2)	0.2480 (2)	0.0656 (7)
N1	0.4138 (2)	0.6950 (2)	0.1306 (2)	0.0552 (8)
H1A	0.3584	0.6663	0.1027	0.066*
N2	0.4512 (3)	0.8761 (3)	0.1662 (2)	0.0642 (9)
C1	0.3189 (3)	0.4915 (3)	0.2306 (3)	0.0685 (11)
C2	0.2938 (5)	0.3838 (5)	0.2467 (4)	0.0973 (16)
H2A	0.2218	0.3628	0.2562	0.117*
C3	0.3751 (6)	0.3079 (4)	0.2485 (4)	0.1067 (18)
H3A	0.3579	0.2349	0.2578	0.128*
C4	0.4787 (5)	0.3375 (4)	0.2371 (5)	0.0959 (15)
H4A	0.5333	0.2851	0.2400	0.115*
C5	0.5061 (4)	0.4451 (3)	0.2210 (3)	0.0684 (11)
H5A	0.5786	0.4647	0.2126	0.082*
C6	0.4249 (3)	0.5240 (3)	0.2174 (3)	0.0567 (10)
C7	0.4632 (3)	0.6395 (3)	0.2022 (3)	0.0517 (10)
C8	0.4501 (4)	0.7972 (3)	0.1011 (3)	0.0638 (11)
C9	0.3979 (4)	0.8690 (3)	0.2597 (3)	0.0694 (12)
H9A	0.4523	0.8763	0.3095	0.083*
H9B	0.3645	0.7979	0.2663	0.083*
C10	0.3114 (4)	0.9563 (4)	0.2731 (4)	0.0733 (13)
C11	0.2355 (5)	0.9757 (5)	0.2031 (5)	0.120 (2)
H11A	0.2383	0.9383	0.1454	0.144*
C12	0.1542 (6)	1.0525 (7)	0.2202 (8)	0.156 (3)
H12A	0.1035	1.0672	0.1726	0.187*
C13	0.1477 (6)	1.1055 (6)	0.3037 (9)	0.137 (3)
H13A	0.0923	1.1556	0.3145	0.164*
C14	0.2215 (7)	1.0855 (5)	0.3709 (6)	0.116 (2)
H14A	0.2171	1.1222	0.4289	0.139*
C15	0.3049 (5)	1.0111 (4)	0.3565 (4)	0.0841 (14)
H15A	0.3562	0.9991	0.4041	0.101*
C16	0.5113 (4)	0.9773 (3)	0.1497 (4)	0.0799 (13)
H16A	0.4655	1.0387	0.1664	0.096*
H16B	0.5292	0.9831	0.0824	0.096*
C17	0.6145 (4)	0.9818 (3)	0.2075 (4)	0.0722 (13)
C18	0.6297 (6)	1.0599 (5)	0.2746 (5)	0.117 (2)
H18A	0.5758	1.1119	0.2839	0.140*
C19	0.7213 (7)	1.0642 (6)	0.3286 (7)	0.161 (4)
H19A	0.7279	1.1164	0.3763	0.193*
C20	0.8018 (6)	0.9934 (7)	0.3131 (6)	0.134 (3)
H20A	0.8672	1.0007	0.3459	0.160*
C21	0.7890 (5)	0.9132 (6)	0.2515 (7)	0.132 (3)
H21A	0.8432	0.8609	0.2443	0.158*
C22	0.6946 (5)	0.9072 (5)	0.1976 (4)	0.1103 (19)
H22A	0.6861	0.8508	0.1539	0.132*

	U11	U22	U33	U12	U13	U23
Br1	0.0739 (3)	0.1215 (4)	0.0970 (4)	−0.0048 (3)	0.0148 (3)	0.0028 (4)
S1	0.1990 (16)	0.0888 (8)	0.0531 (7)	−0.0186 (9)	0.0167 (10)	0.0149 (8)
O1	0.0769 (17)	0.0579 (16)	0.0620 (19)	−0.0059 (14)	−0.0219 (16)	0.0042 (14)
N1	0.064 (2)	0.056 (2)	0.0457 (18)	−0.0031 (16)	−0.0102 (15)	0.0076 (14)
N2	0.082 (2)	0.050 (2)	0.061 (2)	0.0049 (18)	−0.0021 (18)	0.0128 (18)
C1	0.083 (3)	0.072 (3)	0.051 (2)	−0.016 (2)	0.003 (3)	0.007 (2)
C2	0.108 (4)	0.097 (4)	0.087 (4)	−0.042 (4)	0.011 (3)	0.011 (3)
C3	0.156 (6)	0.066 (3)	0.098 (4)	−0.026 (4)	−0.007 (4)	0.014 (3)
C4	0.134 (5)	0.063 (3)	0.090 (4)	0.012 (3)	−0.004 (4)	0.019 (3)
C5	0.092 (3)	0.057 (2)	0.056 (3)	0.000 (2)	−0.005 (2)	0.013 (2)
C6	0.075 (3)	0.055 (2)	0.041 (2)	−0.009 (2)	−0.0036 (19)	0.0091 (18)
C7	0.060 (2)	0.056 (2)	0.039 (2)	0.007 (2)	−0.0019 (18)	0.0025 (17)
C8	0.079 (3)	0.054 (3)	0.058 (3)	0.001 (2)	−0.009 (2)	0.013 (2)
C9	0.076 (3)	0.065 (3)	0.067 (3)	0.006 (2)	−0.003 (2)	0.004 (2)
C10	0.070 (3)	0.056 (3)	0.094 (4)	0.001 (2)	−0.003 (3)	−0.004 (2)
C11	0.110 (4)	0.113 (4)	0.135 (6)	0.034 (4)	−0.056 (4)	−0.034 (4)
C12	0.117 (5)	0.139 (6)	0.212 (10)	0.046 (5)	−0.072 (6)	−0.031 (7)
C13	0.082 (5)	0.090 (5)	0.237 (10)	0.007 (4)	0.039 (6)	−0.006 (6)
C14	0.143 (6)	0.065 (4)	0.140 (6)	−0.003 (4)	0.042 (5)	−0.017 (4)
C15	0.099 (4)	0.058 (3)	0.095 (4)	−0.002 (3)	0.009 (3)	−0.009 (3)
C16	0.109 (4)	0.049 (3)	0.082 (3)	−0.004 (3)	0.005 (3)	0.013 (2)
C17	0.080 (3)	0.048 (2)	0.089 (4)	0.000 (2)	0.011 (3)	−0.002 (2)
C18	0.129 (5)	0.079 (4)	0.143 (5)	0.021 (4)	−0.033 (4)	−0.041 (4)
C19	0.125 (6)	0.128 (5)	0.229 (10)	0.021 (5)	−0.057 (6)	−0.094 (6)
C20	0.095 (5)	0.148 (6)	0.159 (7)	−0.013 (5)	−0.022 (4)	−0.042 (5)
C21	0.087 (4)	0.143 (6)	0.166 (7)	0.027 (4)	0.004 (5)	−0.039 (6)
C22	0.105 (4)	0.110 (4)	0.116 (5)	0.013 (4)	0.007 (4)	−0.041 (3)

Br1—C1	1.909 (4)	C10—C11	1.372 (7)
S1—C8	1.666 (4)	C11—C12	1.394 (10)
O1—C7	1.203 (4)	C11—H11A	0.9300
N1—C7	1.356 (5)	C12—C13	1.341 (11)
N1—C8	1.396 (5)	C12—H12A	0.9300
N1—H1A	0.8602	C13—C14	1.329 (11)
N2—C8	1.330 (5)	C13—H13A	0.9300
N2—C16	1.464 (6)	C14—C15	1.388 (8)
N2—C9	1.467 (5)	C14—H14A	0.9300
C1—C6	1.375 (5)	C15—H15A	0.9300
C1—C2	1.376 (6)	C16—C17	1.505 (7)
C2—C3	1.367 (8)	C16—H16A	0.9700
C2—H2A	0.9300	C16—H16B	0.9700
C3—C4	1.334 (8)	C17—C22	1.352 (7)
C3—H3A	0.9300	C17—C18	1.355 (7)
C4—C5	1.382 (6)	C18—C19	1.356 (9)
C4—H4A	0.9300	C18—H18A	0.9300
C5—C6	1.392 (5)	C19—C20	1.334 (9)
C5—H5A	0.9300	C19—H19A	0.9300
C6—C7	1.509 (5)	C20—C21	1.319 (10)
C9—C10	1.521 (6)	C20—H20A	0.9300
C9—H9A	0.9700	C21—C22	1.386 (9)
C9—H9B	0.9700	C21—H21A	0.9300
C10—C15	1.350 (7)	C22—H22A	0.9300
C7—N1—C8	121.9 (3)	C10—C11—C12	118.7 (6)
C7—N1—H1A	119.0	C10—C11—H11A	120.6
C8—N1—H1A	119.2	C12—C11—H11A	120.6
C8—N2—C16	121.0 (4)	C13—C12—C11	121.4 (7)
C8—N2—C9	124.3 (3)	C13—C12—H12A	119.3
C16—N2—C9	114.6 (4)	C11—C12—H12A	119.3
C6—C1—C2	120.9 (4)	C14—C13—C12	119.1 (7)
C6—C1—Br1	121.7 (3)	C14—C13—H13A	120.4
C2—C1—Br1	117.3 (4)	C12—C13—H13A	120.4
C3—C2—C1	119.7 (5)	C13—C14—C15	121.4 (7)
C3—C2—H2A	120.2	C13—C14—H14A	119.3
C1—C2—H2A	120.2	C15—C14—H14A	119.3
C4—C3—C2	120.6 (5)	C10—C15—C14	119.9 (6)
C4—C3—H3A	119.7	C10—C15—H15A	120.1
C2—C3—H3A	119.7	C14—C15—H15A	120.1
C3—C4—C5	120.8 (5)	N2—C16—C17	111.8 (4)
C3—C4—H4A	119.6	N2—C16—H16A	109.3
C5—C4—H4A	119.6	C17—C16—H16A	109.3
C4—C5—C6	119.9 (5)	N2—C16—H16B	109.3
C4—C5—H5A	120.1	C17—C16—H16B	109.3
C6—C5—H5A	120.1	H16A—C16—H16B	107.9
C1—C6—C5	118.1 (4)	C22—C17—C18	116.8 (5)
C1—C6—C7	126.0 (4)	C22—C17—C16	122.2 (5)
C5—C6—C7	115.9 (4)	C18—C17—C16	121.0 (5)
O1—C7—N1	122.9 (3)	C17—C18—C19	121.9 (6)
O1—C7—C6	121.1 (3)	C17—C18—H18A	119.1
N1—C7—C6	115.9 (3)	C19—C18—H18A	119.1
N2—C8—N1	117.1 (3)	C20—C19—C18	119.9 (7)
N2—C8—S1	125.5 (3)	C20—C19—H19A	120.0
N1—C8—S1	117.4 (3)	C18—C19—H19A	120.0
N2—C9—C10	112.3 (4)	C21—C20—C19	120.3 (7)
N2—C9—H9A	109.1	C21—C20—H20A	119.8
C10—C9—H9A	109.1	C19—C20—H20A	119.8
N2—C9—H9B	109.1	C20—C21—C22	119.7 (6)
C10—C9—H9B	109.1	C20—C21—H21A	120.2
H9A—C9—H9B	107.9	C22—C21—H21A	120.2
C15—C10—C11	119.4 (5)	C17—C22—C21	121.1 (5)
C15—C10—C9	119.9 (5)	C17—C22—H22A	119.4
C11—C10—C9	120.6 (5)	C21—C22—H22A	119.4

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Br1	0.86	2.79	3.220 (3)	113.
N1—H1A···O1i	0.86	2.20	2.903 (4)	139.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Br1	0.86	2.79	3.220 (3)	113
N1—H1A⋯O1i	0.86	2.20	2.903 (4)	139

Symmetry code: (i) .