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In the title compound, C15H13BrN2O2S, the 4-methoxy­benzoyl and 2-bromo­phenyl fragments are located trans and cis, respectively, with respect to the thione group across the C-N bonds. The central carbonyl­thio­urea (N2C2SO) moiety makes dihedral angles with the 4-methoxy­benzoyl and 2-bromo­phenyl fragments of 10.57 (12) and 46.88 (13)°, respectively.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804025590/hg6091sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804025590/hg6091Isup2.hkl
Contains datablock I

CCDC reference: 255909

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.042
  • wR factor = 0.100
  • Data-to-parameter ratio = 15.2

checkCIF/PLATON results

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No errors found in this datablock

Computing details top

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 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

N-(2-Bromophenyl)-N'-(4-methoxybenzoyl)thiourea top
Crystal data top
C15H13BrN2O2SF(000) = 736
Mr = 365.24Dx = 1.629 Mg m3
Monoclinic, P21/nMelting point = 433.9–435.0 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 13.576 (2) ÅCell parameters from 1580 reflections
b = 4.0362 (6) Åθ = 1.5–26.0°
c = 27.495 (4) ŵ = 2.91 mm1
β = 98.621 (3)°T = 293 K
V = 1489.6 (4) Å3Slab, colourless
Z = 40.30 × 0.13 × 0.09 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2891 independent reflections
Radiation source: fine-focus sealed tube2095 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
Detector resolution: 88.66 pixels mm-1θmax = 26.0°, θmin = 1.5°
ω scansh = 1516
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 44
Tmin = 0.471, Tmax = 0.772l = 3333
7392 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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0489P)2 + 0.0218P]
where P = (Fo2 + 2Fc2)/3
2891 reflections(Δ/σ)max < 0.001
190 parametersΔρmax = 0.33 e Å3
0 restraintsΔρmin = 0.22 e Å3
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.91691 (3)0.24916 (10)0.044550 (14)0.06425 (17)
S10.69119 (6)0.3320 (2)0.18377 (3)0.0464 (2)
O11.00933 (17)0.6384 (8)0.17491 (8)0.0691 (8)
O21.23825 (16)0.4963 (7)0.39155 (8)0.0621 (7)
N10.87942 (18)0.4706 (7)0.21192 (9)0.0471 (7)
H1A0.86360.41520.24000.057*
N20.82544 (18)0.5545 (7)0.12959 (9)0.0473 (7)
H2A0.88640.60960.12890.057*
C11.0179 (2)0.3902 (8)0.30274 (12)0.0443 (8)
H1B0.95530.29490.30180.053*
C21.0838 (2)0.3820 (9)0.34541 (12)0.0486 (8)
H2B1.06570.28140.37320.058*
C31.1778 (2)0.5227 (8)0.34770 (11)0.0441 (8)
C41.2045 (2)0.6731 (8)0.30663 (12)0.0451 (8)
H4A1.26710.76900.30780.054*
C51.1371 (2)0.6798 (8)0.26369 (12)0.0429 (8)
H5A1.15530.78170.23600.051*
C61.0432 (2)0.5393 (8)0.26056 (11)0.0379 (7)
C70.9779 (2)0.5551 (9)0.21272 (12)0.0480 (8)
C80.8023 (2)0.4610 (8)0.17318 (11)0.0395 (7)
C90.7602 (2)0.5721 (8)0.08469 (11)0.0410 (7)
C100.7901 (2)0.4484 (8)0.04176 (11)0.0442 (8)
C110.7299 (3)0.4712 (9)0.00280 (12)0.0561 (9)
H11A0.75050.38480.03100.067*
C120.6381 (3)0.6240 (10)0.00549 (13)0.0635 (10)
H12A0.59680.64230.03560.076*
C130.6080 (3)0.7491 (9)0.03651 (14)0.0588 (10)
H13A0.54600.85020.03470.071*
C140.6685 (2)0.7256 (8)0.08067 (12)0.0483 (8)
H14A0.64760.81470.10860.058*
C151.3366 (3)0.6285 (11)0.39567 (14)0.0667 (11)
H15A1.37050.59510.42850.100*
H15B1.33310.86130.38850.100*
H15C1.37230.51800.37280.100*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0535 (2)0.0776 (3)0.0662 (3)0.00495 (19)0.02389 (19)0.00403 (19)
S10.0375 (4)0.0600 (6)0.0429 (5)0.0049 (4)0.0103 (4)0.0035 (4)
O10.0454 (14)0.119 (2)0.0445 (14)0.0192 (14)0.0123 (11)0.0110 (14)
O20.0445 (14)0.092 (2)0.0482 (15)0.0065 (13)0.0018 (11)0.0054 (13)
N10.0366 (14)0.076 (2)0.0308 (14)0.0026 (14)0.0100 (11)0.0008 (13)
N20.0373 (14)0.067 (2)0.0380 (15)0.0068 (14)0.0083 (12)0.0019 (14)
C10.0327 (16)0.052 (2)0.050 (2)0.0006 (15)0.0126 (15)0.0020 (16)
C20.0431 (19)0.059 (2)0.046 (2)0.0009 (16)0.0143 (16)0.0081 (16)
C30.0364 (17)0.053 (2)0.044 (2)0.0029 (15)0.0087 (15)0.0013 (16)
C40.0344 (16)0.054 (2)0.049 (2)0.0048 (15)0.0121 (15)0.0045 (15)
C50.0381 (17)0.051 (2)0.0421 (19)0.0016 (14)0.0146 (15)0.0012 (15)
C60.0328 (16)0.0429 (19)0.0389 (17)0.0001 (14)0.0084 (13)0.0039 (14)
C70.0394 (18)0.059 (2)0.048 (2)0.0046 (16)0.0136 (16)0.0041 (16)
C80.0406 (18)0.044 (2)0.0349 (17)0.0000 (14)0.0088 (14)0.0041 (14)
C90.0384 (17)0.046 (2)0.0389 (18)0.0070 (15)0.0073 (14)0.0058 (15)
C100.0427 (18)0.048 (2)0.044 (2)0.0054 (15)0.0137 (15)0.0030 (15)
C110.070 (2)0.062 (3)0.037 (2)0.010 (2)0.0126 (18)0.0027 (17)
C120.066 (3)0.074 (3)0.047 (2)0.007 (2)0.0054 (19)0.0116 (19)
C130.051 (2)0.067 (3)0.056 (2)0.0050 (19)0.0009 (18)0.0104 (19)
C140.0493 (19)0.052 (2)0.045 (2)0.0029 (16)0.0109 (16)0.0037 (15)
C150.045 (2)0.094 (3)0.058 (2)0.009 (2)0.0028 (18)0.003 (2)
Geometric parameters (Å, º) top
Br1—C101.891 (3)C4—H4A0.9300
S1—C81.662 (3)C5—C61.386 (4)
O1—C71.229 (4)C5—H5A0.9300
O2—C31.357 (3)C6—C71.474 (4)
O2—C151.427 (4)C9—C141.380 (4)
N1—C71.376 (4)C9—C101.397 (4)
N1—C81.378 (4)C10—C111.370 (4)
N1—H1A0.8600C11—C121.382 (5)
N2—C81.338 (4)C11—H11A0.9300
N2—C91.409 (4)C12—C131.377 (5)
N2—H2A0.8600C12—H12A0.9300
C1—C21.365 (4)C13—C141.364 (5)
C1—C61.395 (4)C13—H13A0.9300
C1—H1B0.9300C14—H14A0.9300
C2—C31.389 (4)C15—H15A0.9600
C2—H2B0.9300C15—H15B0.9600
C3—C41.378 (4)C15—H15C0.9600
C4—C51.381 (5)
C3—O2—C15118.4 (3)N2—C8—N1115.6 (3)
C7—N1—C8130.0 (3)N2—C8—S1125.9 (2)
C7—N1—H1A115.0N1—C8—S1118.5 (2)
C8—N1—H1A115.0C14—C9—C10117.8 (3)
C8—N2—C9126.7 (3)C14—C9—N2122.3 (3)
C8—N2—H2A116.7C10—C9—N2119.9 (3)
C9—N2—H2A116.7C11—C10—C9121.4 (3)
C2—C1—C6120.9 (3)C11—C10—Br1118.8 (3)
C2—C1—H1B119.6C9—C10—Br1119.7 (2)
C6—C1—H1B119.6C10—C11—C12119.3 (3)
C1—C2—C3120.6 (3)C10—C11—H11A120.3
C1—C2—H2B119.7C12—C11—H11A120.3
C3—C2—H2B119.7C13—C12—C11119.8 (3)
O2—C3—C4124.4 (3)C13—C12—H12A120.1
O2—C3—C2115.9 (3)C11—C12—H12A120.1
C4—C3—C2119.7 (3)C14—C13—C12120.4 (4)
C3—C4—C5119.2 (3)C14—C13—H13A119.8
C3—C4—H4A120.4C12—C13—H13A119.8
C5—C4—H4A120.4C13—C14—C9121.2 (3)
C4—C5—C6122.0 (3)C13—C14—H14A119.4
C4—C5—H5A119.0C9—C14—H14A119.4
C6—C5—H5A119.0O2—C15—H15A109.5
C5—C6—C1117.6 (3)O2—C15—H15B109.5
C5—C6—C7117.6 (3)H15A—C15—H15B109.5
C1—C6—C7124.8 (3)O2—C15—H15C109.5
O1—C7—N1120.9 (3)H15A—C15—H15C109.5
O1—C7—C6121.9 (3)H15B—C15—H15C109.5
N1—C7—C6117.2 (3)
C6—C1—C2—C30.0 (5)C9—N2—C8—N1178.9 (3)
C15—O2—C3—C40.8 (5)C9—N2—C8—S12.1 (5)
C15—O2—C3—C2178.4 (3)C7—N1—C8—N21.6 (5)
C1—C2—C3—O2178.9 (3)C7—N1—C8—S1177.5 (3)
C1—C2—C3—C40.3 (5)C8—N2—C9—C1448.3 (5)
O2—C3—C4—C5178.8 (3)C8—N2—C9—C10135.4 (3)
C2—C3—C4—C50.3 (5)C14—C9—C10—C111.4 (5)
C3—C4—C5—C60.0 (5)N2—C9—C10—C11177.8 (3)
C4—C5—C6—C10.4 (4)C14—C9—C10—Br1177.8 (2)
C4—C5—C6—C7178.9 (3)N2—C9—C10—Br11.4 (4)
C2—C1—C6—C50.4 (5)C9—C10—C11—C120.9 (5)
C2—C1—C6—C7178.9 (3)Br1—C10—C11—C12178.3 (3)
C8—N1—C7—O10.1 (6)C10—C11—C12—C130.4 (6)
C8—N1—C7—C6179.7 (3)C11—C12—C13—C140.5 (6)
C5—C6—C7—O111.8 (5)C12—C13—C14—C91.1 (5)
C1—C6—C7—O1167.4 (3)C10—C9—C14—C131.5 (5)
C5—C6—C7—N1168.5 (3)N2—C9—C14—C13177.8 (3)
C1—C6—C7—N112.2 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O10.861.942.640 (3)138
C14—H14A···S10.932.843.224 (3)106
C1—H1B···S1i0.932.803.686 (3)160
N1—H1A···S1ii0.862.873.478 (3)129
Symmetry codes: (i) x+3/2, y1/2, z+1/2; (ii) x+3/2, y+1/2, z+1/2.
 

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