N′-Benzoyl-N-p-bromo­phenyl­thio­urea

In the title compound, C₁₄H₁₁BrN₂OS, the bromophenyl and benzoyl groups lie cis and trans, respectively, to the S atom across the thio­urea C—N bonds. Owing to the presence of the Br atom in the para position, the dihedral angle between the bromophenyl group and the central carbonyl­thio­urea plane is increased to 20.40 (11)°, in comparison with 7.52 (9)° in its unsubstituted phenyl analogue. The mol­ecules are linked by intermolecular contacts N—H...S and C—H...O to form linear chains parallel to the a axis.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.033
• wR factor = 0.091
• Data-to-parameter ratio = 17.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes



ABSTM_02  When printed, the submitted absorption T values will be replaced
          by the scaled T values. Since the ratio of scaled T's is
          identical to the ratio of reported T values, the scaling does
          not imply a change to the absorption corrections used in the
          study.
          Ratio of Tmax expected/reported      0.921
          Tmax scaled      0.499 Tmin scaled      0.388

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).

N-para-bromophenyl-N'-benzoylthiourea

Crystal data

C14H11BrN2OS	F(000) = 672
Mr = 335.22	Dx = 1.637 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.846 (3) Å	Cell parameters from 2075 reflections
b = 5.9486 (14) Å	θ = 1.5–27.5°
c = 16.972 (4) Å	µ = 3.16 mm^−1
β = 103.311 (4)°	T = 273 K
V = 1360.3 (6) Å^3	Block, colourless
Z = 4	0.33 × 0.30 × 0.22 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer	3081 independent reflections
Radiation source: fine-focus sealed tube	2284 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
Detector resolution: 83.66 pixels mm^-1	θmax = 27.5°, θmin = 1.5°
ω scans	h = −12→17
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	k = −7→7
Tmin = 0.421, Tmax = 0.542	l = −21→22
7554 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.091	H-atom parameters constrained
S = 0.91	w = 1/[σ^2(Fo^2) + (0.0511P)^2 + 0.2498P] where P = (Fo^2 + 2Fc^2)/3
3081 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.41 e Å^−3
0 restraints	Δρmin = −0.48 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.01734 (2)	−0.79273 (5)	1.181023 (19)	0.05398 (13)
S1	0.42452 (5)	−0.28673 (13)	1.03348 (5)	0.0542 (2)
N2	0.23294 (15)	−0.1636 (3)	0.99858 (14)	0.0418 (5)
H2A	0.1913	−0.0697	0.9710	0.050*
O1	0.17969 (14)	0.1708 (3)	0.89885 (13)	0.0546 (5)
C12	0.08809 (17)	−0.5974 (4)	1.12586 (15)	0.0369 (5)
C7	0.26637 (19)	0.1778 (4)	0.89443 (16)	0.0406 (6)
C9	0.18987 (18)	−0.3196 (4)	1.04365 (15)	0.0356 (5)
C8	0.32534 (17)	−0.1355 (4)	0.99101 (15)	0.0369 (5)
C13	0.17833 (19)	−0.6632 (4)	1.11359 (17)	0.0413 (6)
H13A	0.2051	−0.8011	1.1333	0.050*
C1	0.3775 (2)	0.2848 (5)	0.80210 (18)	0.0483 (7)
H1A	0.4133	0.1524	0.8151	0.058*
C14	0.22957 (18)	−0.5251 (4)	1.07205 (16)	0.0421 (6)
H14A	0.2905	−0.5702	1.0632	0.051*
N1	0.33758 (15)	0.0423 (3)	0.94071 (13)	0.0421 (5)
H1B	0.3977	0.0709	0.9384	0.051*
C10	0.09817 (19)	−0.2553 (4)	1.05700 (17)	0.0404 (6)
H10A	0.0710	−0.1175	1.0376	0.048*
C6	0.29995 (18)	0.3344 (4)	0.83817 (15)	0.0387 (6)
C11	0.04735 (18)	−0.3934 (4)	1.09848 (16)	0.0412 (6)
H11A	−0.0135	−0.3494	1.1078	0.049*
C5	0.2469 (2)	0.5315 (4)	0.81750 (17)	0.0474 (6)
H5A	0.1934	0.5638	0.8401	0.057*
C3	0.3507 (2)	0.6300 (6)	0.72896 (19)	0.0636 (9)
H3A	0.3689	0.7313	0.6932	0.076*
C2	0.4016 (2)	0.4321 (6)	0.74676 (19)	0.0622 (8)
H2B	0.4526	0.3969	0.7215	0.075*
C4	0.2730 (2)	0.6795 (5)	0.7638 (2)	0.0589 (8)
H4A	0.2380	0.8132	0.7511	0.071*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0507 (2)	0.04973 (18)	0.0683 (2)	−0.00084 (13)	0.02749 (16)	0.01107 (13)
S1	0.0296 (4)	0.0623 (4)	0.0708 (5)	0.0057 (3)	0.0117 (3)	0.0240 (4)
N2	0.0291 (11)	0.0460 (12)	0.0515 (14)	0.0049 (9)	0.0117 (10)	0.0109 (10)
O1	0.0310 (10)	0.0654 (13)	0.0684 (14)	0.0071 (9)	0.0139 (9)	0.0208 (10)
C12	0.0323 (13)	0.0379 (12)	0.0411 (14)	−0.0040 (10)	0.0102 (11)	−0.0020 (11)
C7	0.0335 (14)	0.0466 (15)	0.0432 (15)	0.0009 (11)	0.0116 (11)	0.0024 (11)
C9	0.0296 (12)	0.0400 (13)	0.0371 (13)	−0.0027 (10)	0.0077 (10)	−0.0009 (10)
C8	0.0303 (13)	0.0430 (12)	0.0364 (14)	0.0000 (10)	0.0052 (10)	0.0013 (11)
C13	0.0358 (14)	0.0340 (12)	0.0536 (17)	0.0016 (10)	0.0095 (12)	0.0007 (11)
C1	0.0347 (14)	0.0612 (16)	0.0472 (17)	0.0012 (13)	0.0055 (12)	0.0126 (13)
C14	0.0326 (13)	0.0391 (13)	0.0567 (17)	0.0034 (11)	0.0144 (12)	−0.0024 (12)
N1	0.0270 (10)	0.0506 (12)	0.0498 (13)	0.0017 (9)	0.0109 (9)	0.0121 (10)
C10	0.0326 (14)	0.0386 (12)	0.0504 (16)	0.0054 (10)	0.0105 (12)	0.0078 (11)
C6	0.0328 (13)	0.0442 (14)	0.0362 (14)	−0.0041 (10)	0.0018 (10)	0.0036 (11)
C11	0.0292 (12)	0.0451 (13)	0.0518 (16)	0.0025 (11)	0.0143 (11)	0.0005 (12)
C5	0.0432 (15)	0.0467 (14)	0.0482 (17)	0.0022 (12)	0.0019 (12)	0.0013 (13)
C3	0.0556 (19)	0.0696 (19)	0.059 (2)	−0.0177 (16)	−0.0009 (15)	0.0250 (17)
C2	0.0426 (16)	0.087 (2)	0.057 (2)	−0.0048 (16)	0.0123 (14)	0.0220 (17)
C4	0.057 (2)	0.0463 (16)	0.064 (2)	−0.0022 (14)	−0.0033 (16)	0.0145 (14)

Geometric parameters (Å, º)

Br1—C12	1.900 (2)	C1—C6	1.385 (4)
S1—C8	1.661 (3)	C1—H1A	0.9300
N2—C8	1.325 (3)	C14—H14A	0.9300
N2—C9	1.418 (3)	N1—H1B	0.8600
N2—H2A	0.8600	C10—C11	1.376 (3)
O1—C7	1.220 (3)	C10—H10A	0.9300
C12—C13	1.370 (3)	C6—C5	1.385 (3)
C12—C11	1.373 (3)	C11—H11A	0.9300
C7—N1	1.372 (3)	C5—C4	1.374 (4)
C7—C6	1.483 (3)	C5—H5A	0.9300
C9—C14	1.381 (3)	C3—C2	1.369 (5)
C9—C10	1.393 (3)	C3—C4	1.374 (5)
C8—N1	1.394 (3)	C3—H3A	0.9300
C13—C14	1.380 (3)	C2—H2B	0.9300
C13—H13A	0.9300	C4—H4A	0.9300
C1—C2	1.381 (4)
C8—N2—C9	132.1 (2)	C7—N1—C8	128.6 (2)
C8—N2—H2A	114.0	C7—N1—H1B	115.7
C9—N2—H2A	114.0	C8—N1—H1B	115.7
C13—C12—C11	121.3 (2)	C11—C10—C9	120.8 (2)
C13—C12—Br1	119.47 (19)	C11—C10—H10A	119.6
C11—C12—Br1	119.28 (17)	C9—C10—H10A	119.6
O1—C7—N1	122.1 (2)	C5—C6—C1	119.2 (2)
O1—C7—C6	121.3 (2)	C5—C6—C7	117.9 (2)
N1—C7—C6	116.6 (2)	C1—C6—C7	122.7 (2)
C14—C9—C10	119.4 (2)	C12—C11—C10	118.8 (2)
C14—C9—N2	125.8 (2)	C12—C11—H11A	120.6
C10—C9—N2	114.9 (2)	C10—C11—H11A	120.6
N2—C8—N1	114.3 (2)	C4—C5—C6	120.4 (3)
N2—C8—S1	127.57 (19)	C4—C5—H5A	119.8
N1—C8—S1	118.15 (18)	C6—C5—H5A	119.8
C12—C13—C14	120.1 (2)	C2—C3—C4	120.2 (3)
C12—C13—H13A	119.9	C2—C3—H3A	119.9
C14—C13—H13A	119.9	C4—C3—H3A	119.9
C2—C1—C6	119.9 (3)	C3—C2—C1	120.2 (3)
C2—C1—H1A	120.0	C3—C2—H2B	119.9
C6—C1—H1A	120.0	C1—C2—H2B	119.9
C13—C14—C9	119.7 (2)	C5—C4—C3	120.0 (3)
C13—C14—H14A	120.2	C5—C4—H4A	120.0
C9—C14—H14A	120.2	C3—C4—H4A	120.0
C8—N2—C9—C14	−21.3 (4)	C2—C1—C6—C5	0.5 (4)
C8—N2—C9—C10	160.6 (3)	C2—C1—C6—C7	176.4 (3)
C9—N2—C8—N1	−179.2 (2)	O1—C7—C6—C5	27.4 (4)
C9—N2—C8—S1	1.2 (4)	N1—C7—C6—C5	−152.7 (2)
C11—C12—C13—C14	−0.9 (4)	O1—C7—C6—C1	−148.5 (3)
Br1—C12—C13—C14	178.6 (2)	N1—C7—C6—C1	31.4 (4)
C12—C13—C14—C9	0.6 (4)	C13—C12—C11—C10	0.9 (4)
C10—C9—C14—C13	−0.4 (4)	Br1—C12—C11—C10	−178.6 (2)
N2—C9—C14—C13	−178.4 (3)	C9—C10—C11—C12	−0.7 (4)
O1—C7—N1—C8	7.9 (4)	C1—C6—C5—C4	−2.1 (4)
C6—C7—N1—C8	−172.0 (2)	C7—C6—C5—C4	−178.1 (3)
N2—C8—N1—C7	−5.3 (4)	C4—C3—C2—C1	−2.4 (5)
S1—C8—N1—C7	174.3 (2)	C6—C1—C2—C3	1.7 (5)
C14—C9—C10—C11	0.4 (4)	C6—C5—C4—C3	1.4 (5)
N2—C9—C10—C11	178.7 (2)	C2—C3—C4—C5	0.8 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1	0.86	1.87	2.606 (3)	143
C14—H14A···S1	0.93	2.64	3.246 (3)	123
N1—H1B···S1^i	0.86	2.72	3.534 (2)	158
C11—H11A···O1^ii	0.93	2.51	3.421 (3)	165

Symmetry codes: (i) −x+1, −y, −z+2; (ii) −x, −y, −z+2.