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
CCDC reference: 255909
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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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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
C15H13BrN2O2S | F(000) = 736 |
Mr = 365.24 | Dx = 1.629 Mg m−3 |
Monoclinic, P21/n | Melting point = 433.9–435.0 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 13.576 (2) Å | Cell parameters from 1580 reflections |
b = 4.0362 (6) Å | θ = 1.5–26.0° |
c = 27.495 (4) Å | µ = 2.91 mm−1 |
β = 98.621 (3)° | T = 293 K |
V = 1489.6 (4) Å3 | Slab, colourless |
Z = 4 | 0.30 × 0.13 × 0.09 mm |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 2891 independent reflections |
Radiation source: fine-focus sealed tube | 2095 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
Detector resolution: 88.66 pixels mm-1 | θmax = 26.0°, θmin = 1.5° |
ω scans | h = −15→16 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −4→4 |
Tmin = 0.471, Tmax = 0.772 | l = −33→33 |
7392 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.100 | H-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 parameters | Δρmax = 0.33 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
Br1 | 0.91691 (3) | 0.24916 (10) | 0.044550 (14) | 0.06425 (17) | |
S1 | 0.69119 (6) | 0.3320 (2) | 0.18377 (3) | 0.0464 (2) | |
O1 | 1.00933 (17) | 0.6384 (8) | 0.17491 (8) | 0.0691 (8) | |
O2 | 1.23825 (16) | 0.4963 (7) | 0.39155 (8) | 0.0621 (7) | |
N1 | 0.87942 (18) | 0.4706 (7) | 0.21192 (9) | 0.0471 (7) | |
H1A | 0.8636 | 0.4152 | 0.2400 | 0.057* | |
N2 | 0.82544 (18) | 0.5545 (7) | 0.12959 (9) | 0.0473 (7) | |
H2A | 0.8864 | 0.6096 | 0.1289 | 0.057* | |
C1 | 1.0179 (2) | 0.3902 (8) | 0.30274 (12) | 0.0443 (8) | |
H1B | 0.9553 | 0.2949 | 0.3018 | 0.053* | |
C2 | 1.0838 (2) | 0.3820 (9) | 0.34541 (12) | 0.0486 (8) | |
H2B | 1.0657 | 0.2814 | 0.3732 | 0.058* | |
C3 | 1.1778 (2) | 0.5227 (8) | 0.34770 (11) | 0.0441 (8) | |
C4 | 1.2045 (2) | 0.6731 (8) | 0.30663 (12) | 0.0451 (8) | |
H4A | 1.2671 | 0.7690 | 0.3078 | 0.054* | |
C5 | 1.1371 (2) | 0.6798 (8) | 0.26369 (12) | 0.0429 (8) | |
H5A | 1.1553 | 0.7817 | 0.2360 | 0.051* | |
C6 | 1.0432 (2) | 0.5393 (8) | 0.26056 (11) | 0.0379 (7) | |
C7 | 0.9779 (2) | 0.5551 (9) | 0.21272 (12) | 0.0480 (8) | |
C8 | 0.8023 (2) | 0.4610 (8) | 0.17318 (11) | 0.0395 (7) | |
C9 | 0.7602 (2) | 0.5721 (8) | 0.08469 (11) | 0.0410 (7) | |
C10 | 0.7901 (2) | 0.4484 (8) | 0.04176 (11) | 0.0442 (8) | |
C11 | 0.7299 (3) | 0.4712 (9) | −0.00280 (12) | 0.0561 (9) | |
H11A | 0.7505 | 0.3848 | −0.0310 | 0.067* | |
C12 | 0.6381 (3) | 0.6240 (10) | −0.00549 (13) | 0.0635 (10) | |
H12A | 0.5968 | 0.6423 | −0.0356 | 0.076* | |
C13 | 0.6080 (3) | 0.7491 (9) | 0.03651 (14) | 0.0588 (10) | |
H13A | 0.5460 | 0.8502 | 0.0347 | 0.071* | |
C14 | 0.6685 (2) | 0.7256 (8) | 0.08067 (12) | 0.0483 (8) | |
H14A | 0.6476 | 0.8147 | 0.1086 | 0.058* | |
C15 | 1.3366 (3) | 0.6285 (11) | 0.39567 (14) | 0.0667 (11) | |
H15A | 1.3705 | 0.5951 | 0.4285 | 0.100* | |
H15B | 1.3331 | 0.8613 | 0.3885 | 0.100* | |
H15C | 1.3723 | 0.5180 | 0.3728 | 0.100* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.0535 (2) | 0.0776 (3) | 0.0662 (3) | 0.00495 (19) | 0.02389 (19) | −0.00403 (19) |
S1 | 0.0375 (4) | 0.0600 (6) | 0.0429 (5) | −0.0049 (4) | 0.0103 (4) | 0.0035 (4) |
O1 | 0.0454 (14) | 0.119 (2) | 0.0445 (14) | −0.0192 (14) | 0.0123 (11) | 0.0110 (14) |
O2 | 0.0445 (14) | 0.092 (2) | 0.0482 (15) | −0.0065 (13) | 0.0018 (11) | 0.0054 (13) |
N1 | 0.0366 (14) | 0.076 (2) | 0.0308 (14) | −0.0026 (14) | 0.0100 (11) | −0.0008 (13) |
N2 | 0.0373 (14) | 0.067 (2) | 0.0380 (15) | −0.0068 (14) | 0.0083 (12) | 0.0019 (14) |
C1 | 0.0327 (16) | 0.052 (2) | 0.050 (2) | −0.0006 (15) | 0.0126 (15) | 0.0020 (16) |
C2 | 0.0431 (19) | 0.059 (2) | 0.046 (2) | −0.0009 (16) | 0.0143 (16) | 0.0081 (16) |
C3 | 0.0364 (17) | 0.053 (2) | 0.044 (2) | 0.0029 (15) | 0.0087 (15) | −0.0013 (16) |
C4 | 0.0344 (16) | 0.054 (2) | 0.049 (2) | −0.0048 (15) | 0.0121 (15) | −0.0045 (15) |
C5 | 0.0381 (17) | 0.051 (2) | 0.0421 (19) | −0.0016 (14) | 0.0146 (15) | −0.0012 (15) |
C6 | 0.0328 (16) | 0.0429 (19) | 0.0389 (17) | 0.0001 (14) | 0.0084 (13) | −0.0039 (14) |
C7 | 0.0394 (18) | 0.059 (2) | 0.048 (2) | −0.0046 (16) | 0.0136 (16) | −0.0041 (16) |
C8 | 0.0406 (18) | 0.044 (2) | 0.0349 (17) | 0.0000 (14) | 0.0088 (14) | −0.0041 (14) |
C9 | 0.0384 (17) | 0.046 (2) | 0.0389 (18) | −0.0070 (15) | 0.0073 (14) | 0.0058 (15) |
C10 | 0.0427 (18) | 0.048 (2) | 0.044 (2) | −0.0054 (15) | 0.0137 (15) | 0.0030 (15) |
C11 | 0.070 (2) | 0.062 (3) | 0.037 (2) | −0.010 (2) | 0.0126 (18) | 0.0027 (17) |
C12 | 0.066 (3) | 0.074 (3) | 0.047 (2) | −0.007 (2) | −0.0054 (19) | 0.0116 (19) |
C13 | 0.051 (2) | 0.067 (3) | 0.056 (2) | 0.0050 (19) | 0.0009 (18) | 0.0104 (19) |
C14 | 0.0493 (19) | 0.052 (2) | 0.045 (2) | 0.0029 (16) | 0.0109 (16) | 0.0037 (15) |
C15 | 0.045 (2) | 0.094 (3) | 0.058 (2) | −0.009 (2) | −0.0028 (18) | −0.003 (2) |
Geometric parameters (Å, º) top
Br1—C10 | 1.891 (3) | C4—H4A | 0.9300 |
S1—C8 | 1.662 (3) | C5—C6 | 1.386 (4) |
O1—C7 | 1.229 (4) | C5—H5A | 0.9300 |
O2—C3 | 1.357 (3) | C6—C7 | 1.474 (4) |
O2—C15 | 1.427 (4) | C9—C14 | 1.380 (4) |
N1—C7 | 1.376 (4) | C9—C10 | 1.397 (4) |
N1—C8 | 1.378 (4) | C10—C11 | 1.370 (4) |
N1—H1A | 0.8600 | C11—C12 | 1.382 (5) |
N2—C8 | 1.338 (4) | C11—H11A | 0.9300 |
N2—C9 | 1.409 (4) | C12—C13 | 1.377 (5) |
N2—H2A | 0.8600 | C12—H12A | 0.9300 |
C1—C2 | 1.365 (4) | C13—C14 | 1.364 (5) |
C1—C6 | 1.395 (4) | C13—H13A | 0.9300 |
C1—H1B | 0.9300 | C14—H14A | 0.9300 |
C2—C3 | 1.389 (4) | C15—H15A | 0.9600 |
C2—H2B | 0.9300 | C15—H15B | 0.9600 |
C3—C4 | 1.378 (4) | C15—H15C | 0.9600 |
C4—C5 | 1.381 (5) | | |
| | | |
C3—O2—C15 | 118.4 (3) | N2—C8—N1 | 115.6 (3) |
C7—N1—C8 | 130.0 (3) | N2—C8—S1 | 125.9 (2) |
C7—N1—H1A | 115.0 | N1—C8—S1 | 118.5 (2) |
C8—N1—H1A | 115.0 | C14—C9—C10 | 117.8 (3) |
C8—N2—C9 | 126.7 (3) | C14—C9—N2 | 122.3 (3) |
C8—N2—H2A | 116.7 | C10—C9—N2 | 119.9 (3) |
C9—N2—H2A | 116.7 | C11—C10—C9 | 121.4 (3) |
C2—C1—C6 | 120.9 (3) | C11—C10—Br1 | 118.8 (3) |
C2—C1—H1B | 119.6 | C9—C10—Br1 | 119.7 (2) |
C6—C1—H1B | 119.6 | C10—C11—C12 | 119.3 (3) |
C1—C2—C3 | 120.6 (3) | C10—C11—H11A | 120.3 |
C1—C2—H2B | 119.7 | C12—C11—H11A | 120.3 |
C3—C2—H2B | 119.7 | C13—C12—C11 | 119.8 (3) |
O2—C3—C4 | 124.4 (3) | C13—C12—H12A | 120.1 |
O2—C3—C2 | 115.9 (3) | C11—C12—H12A | 120.1 |
C4—C3—C2 | 119.7 (3) | C14—C13—C12 | 120.4 (4) |
C3—C4—C5 | 119.2 (3) | C14—C13—H13A | 119.8 |
C3—C4—H4A | 120.4 | C12—C13—H13A | 119.8 |
C5—C4—H4A | 120.4 | C13—C14—C9 | 121.2 (3) |
C4—C5—C6 | 122.0 (3) | C13—C14—H14A | 119.4 |
C4—C5—H5A | 119.0 | C9—C14—H14A | 119.4 |
C6—C5—H5A | 119.0 | O2—C15—H15A | 109.5 |
C5—C6—C1 | 117.6 (3) | O2—C15—H15B | 109.5 |
C5—C6—C7 | 117.6 (3) | H15A—C15—H15B | 109.5 |
C1—C6—C7 | 124.8 (3) | O2—C15—H15C | 109.5 |
O1—C7—N1 | 120.9 (3) | H15A—C15—H15C | 109.5 |
O1—C7—C6 | 121.9 (3) | H15B—C15—H15C | 109.5 |
N1—C7—C6 | 117.2 (3) | | |
| | | |
C6—C1—C2—C3 | 0.0 (5) | C9—N2—C8—N1 | −178.9 (3) |
C15—O2—C3—C4 | −0.8 (5) | C9—N2—C8—S1 | 2.1 (5) |
C15—O2—C3—C2 | 178.4 (3) | C7—N1—C8—N2 | −1.6 (5) |
C1—C2—C3—O2 | −178.9 (3) | C7—N1—C8—S1 | 177.5 (3) |
C1—C2—C3—C4 | 0.3 (5) | C8—N2—C9—C14 | 48.3 (5) |
O2—C3—C4—C5 | 178.8 (3) | C8—N2—C9—C10 | −135.4 (3) |
C2—C3—C4—C5 | −0.3 (5) | C14—C9—C10—C11 | −1.4 (5) |
C3—C4—C5—C6 | 0.0 (5) | N2—C9—C10—C11 | −177.8 (3) |
C4—C5—C6—C1 | 0.4 (4) | C14—C9—C10—Br1 | 177.8 (2) |
C4—C5—C6—C7 | −178.9 (3) | N2—C9—C10—Br1 | 1.4 (4) |
C2—C1—C6—C5 | −0.4 (5) | C9—C10—C11—C12 | 0.9 (5) |
C2—C1—C6—C7 | 178.9 (3) | Br1—C10—C11—C12 | −178.3 (3) |
C8—N1—C7—O1 | −0.1 (6) | C10—C11—C12—C13 | −0.4 (6) |
C8—N1—C7—C6 | −179.7 (3) | C11—C12—C13—C14 | 0.5 (6) |
C5—C6—C7—O1 | 11.8 (5) | C12—C13—C14—C9 | −1.1 (5) |
C1—C6—C7—O1 | −167.4 (3) | C10—C9—C14—C13 | 1.5 (5) |
C5—C6—C7—N1 | −168.5 (3) | N2—C9—C14—C13 | 177.8 (3) |
C1—C6—C7—N1 | 12.2 (5) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O1 | 0.86 | 1.94 | 2.640 (3) | 138 |
C14—H14A···S1 | 0.93 | 2.84 | 3.224 (3) | 106 |
C1—H1B···S1i | 0.93 | 2.80 | 3.686 (3) | 160 |
N1—H1A···S1ii | 0.86 | 2.87 | 3.478 (3) | 129 |
Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) −x+3/2, y+1/2, −z+1/2. |