Buy article online - an online subscription or single-article purchase is required to access this article.
organic compounds
In the title compound, C15H13ClN2O2S, the dihedral angle between the 2-chlorophenyl and 4-methoxyphenyl groups is 54.12 (13)°. The molecule is stabilized by intermolecular C—HS and N—HS interactions, forming double-column chains arranged parallel to the b axis.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804024985/ac6114sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804024985/ac6114Isup2.hkl |
CCDC reference: 255892
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.004 Å
- R factor = 0.059
- wR factor = 0.140
- Data-to-parameter ratio = 16.6
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT414_ALERT_2_C Short Intra D-H..H-X H1 .. H1A .. 1.99 Ang. PLAT420_ALERT_2_C D-H Without Acceptor N1 - H1 ... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
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-Chlorophenyl)-N-(4-methoxybenzoyl)thiourea top
Crystal data top
C15H13ClN2O2S | F(000) = 664 |
Mr = 320.78 | Dx = 1.453 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 13.438 (3) Å | Cell parameters from 2167 reflections |
b = 3.9893 (9) Å | θ = 1.5–27.0° |
c = 27.727 (6) Å | µ = 0.41 mm−1 |
β = 99.508 (4)° | T = 273 K |
V = 1466.0 (5) Å3 | Block, colourless |
Z = 4 | 0.22 × 0.19 × 0.16 mm |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 3162 independent reflections |
Radiation source: fine-focus sealed tube | 2649 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
Detector resolution: 83.66 pixels mm-1 | θmax = 27.0°, θmin = 1.5° |
ω scans | h = −13→17 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −5→5 |
Tmin = 0.916, Tmax = 0.938 | l = −35→27 |
7879 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)] = 0.059 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.140 | H-atom parameters constrained |
S = 1.19 | w = 1/[σ2(Fo2) + (0.0589P)2 + 0.3777P] where P = (Fo2 + 2Fc2)/3 |
3162 reflections | (Δ/σ)max = 0.001 |
191 parameters | Δρmax = 0.33 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.41573 (6) | −0.2117 (2) | 0.04847 (3) | 0.0738 (3) | |
S1 | 0.19169 (4) | −0.16876 (18) | 0.18381 (2) | 0.0447 (2) | |
O1 | 0.51528 (14) | 0.1285 (6) | 0.17833 (7) | 0.0692 (6) | |
O2 | 0.74579 (13) | −0.0232 (6) | 0.39513 (6) | 0.0591 (5) | |
N1 | 0.38261 (14) | −0.0358 (6) | 0.21388 (7) | 0.0447 (5) | |
H1 | 0.3662 | −0.0932 | 0.2414 | 0.054* | |
N2 | 0.32877 (15) | 0.0564 (6) | 0.13186 (7) | 0.0461 (5) | |
H2 | 0.3907 | 0.1115 | 0.1321 | 0.055* | |
C1 | 0.52146 (17) | −0.1171 (6) | 0.30500 (9) | 0.0431 (6) | |
H1A | 0.4575 | −0.2097 | 0.3034 | 0.052* | |
C2 | 0.58848 (19) | −0.1278 (7) | 0.34809 (9) | 0.0479 (6) | |
H2A | 0.5693 | −0.2264 | 0.3755 | 0.057* | |
C3 | 0.68438 (17) | 0.0068 (7) | 0.35105 (8) | 0.0425 (6) | |
C4 | 0.71249 (18) | 0.1590 (7) | 0.31041 (9) | 0.0434 (6) | |
H4 | 0.7762 | 0.2540 | 0.3122 | 0.052* | |
C5 | 0.64447 (17) | 0.1672 (7) | 0.26735 (9) | 0.0435 (6) | |
H5 | 0.6636 | 0.2670 | 0.2400 | 0.052* | |
C6 | 0.54857 (17) | 0.0317 (6) | 0.26356 (8) | 0.0391 (5) | |
C7 | 0.48254 (18) | 0.0471 (7) | 0.21546 (9) | 0.0456 (6) | |
C8 | 0.30453 (17) | −0.0402 (6) | 0.17439 (8) | 0.0394 (5) | |
C9 | 0.26362 (18) | 0.0783 (6) | 0.08634 (8) | 0.0410 (6) | |
C10 | 0.29672 (19) | −0.0371 (7) | 0.04432 (9) | 0.0484 (6) | |
C11 | 0.2368 (2) | −0.0077 (8) | −0.00068 (9) | 0.0596 (7) | |
H11 | 0.2599 | −0.0835 | −0.0286 | 0.072* | |
C12 | 0.1427 (2) | 0.1335 (9) | −0.00446 (10) | 0.0639 (8) | |
H12 | 0.1018 | 0.1509 | −0.0349 | 0.077* | |
C13 | 0.1088 (2) | 0.2491 (8) | 0.03648 (10) | 0.0591 (8) | |
H13 | 0.0449 | 0.3437 | 0.0338 | 0.071* | |
C14 | 0.16971 (19) | 0.2252 (7) | 0.08169 (9) | 0.0495 (6) | |
H14 | 0.1471 | 0.3090 | 0.1092 | 0.059* | |
C15 | 0.8456 (2) | 0.1038 (9) | 0.39970 (10) | 0.0648 (9) | |
H15A | 0.8808 | −0.0104 | 0.3771 | 0.097* | |
H15B | 0.8801 | 0.0681 | 0.4325 | 0.097* | |
H15C | 0.8433 | 0.3394 | 0.3926 | 0.097* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0559 (4) | 0.1049 (7) | 0.0652 (5) | 0.0132 (4) | 0.0234 (4) | −0.0060 (4) |
S1 | 0.0371 (3) | 0.0562 (4) | 0.0415 (3) | −0.0043 (3) | 0.0086 (2) | 0.0024 (3) |
O1 | 0.0446 (10) | 0.123 (2) | 0.0415 (10) | −0.0171 (11) | 0.0107 (8) | 0.0116 (11) |
O2 | 0.0448 (10) | 0.0889 (15) | 0.0420 (10) | −0.0067 (10) | 0.0023 (8) | 0.0063 (10) |
N1 | 0.0359 (10) | 0.0672 (15) | 0.0320 (10) | −0.0029 (10) | 0.0087 (8) | 0.0005 (9) |
N2 | 0.0365 (10) | 0.0672 (15) | 0.0359 (10) | −0.0049 (10) | 0.0096 (8) | 0.0027 (10) |
C1 | 0.0337 (12) | 0.0491 (15) | 0.0487 (14) | −0.0031 (10) | 0.0130 (10) | 0.0010 (11) |
C2 | 0.0440 (14) | 0.0608 (17) | 0.0417 (13) | −0.0015 (12) | 0.0152 (11) | 0.0093 (12) |
C3 | 0.0401 (12) | 0.0494 (15) | 0.0381 (12) | 0.0015 (11) | 0.0066 (10) | −0.0040 (11) |
C4 | 0.0345 (12) | 0.0520 (15) | 0.0456 (13) | −0.0046 (11) | 0.0123 (10) | −0.0051 (11) |
C5 | 0.0385 (12) | 0.0530 (15) | 0.0421 (13) | −0.0037 (11) | 0.0153 (10) | 0.0010 (11) |
C6 | 0.0353 (12) | 0.0449 (14) | 0.0388 (12) | −0.0003 (10) | 0.0112 (9) | −0.0021 (10) |
C7 | 0.0383 (12) | 0.0585 (17) | 0.0417 (13) | −0.0021 (12) | 0.0114 (10) | −0.0011 (12) |
C8 | 0.0383 (12) | 0.0439 (14) | 0.0372 (12) | 0.0013 (10) | 0.0094 (10) | −0.0037 (10) |
C9 | 0.0419 (13) | 0.0449 (15) | 0.0364 (12) | −0.0051 (10) | 0.0065 (10) | 0.0031 (10) |
C10 | 0.0487 (14) | 0.0564 (17) | 0.0419 (13) | −0.0022 (12) | 0.0126 (11) | 0.0013 (12) |
C11 | 0.0739 (19) | 0.070 (2) | 0.0365 (13) | −0.0073 (16) | 0.0129 (13) | −0.0019 (13) |
C12 | 0.0679 (19) | 0.077 (2) | 0.0413 (15) | −0.0043 (16) | −0.0072 (13) | 0.0094 (14) |
C13 | 0.0568 (17) | 0.064 (2) | 0.0541 (16) | 0.0059 (14) | 0.0011 (13) | 0.0130 (14) |
C14 | 0.0510 (15) | 0.0549 (17) | 0.0436 (14) | 0.0053 (12) | 0.0109 (11) | 0.0038 (12) |
C15 | 0.0448 (15) | 0.090 (3) | 0.0564 (17) | −0.0103 (15) | −0.0017 (13) | −0.0012 (16) |
Geometric parameters (Å, º) top
Cl1—C10 | 1.731 (3) | C4—H4 | 0.9300 |
S1—C8 | 1.662 (2) | C5—C6 | 1.385 (3) |
O1—C7 | 1.228 (3) | C5—H5 | 0.9300 |
O2—C3 | 1.362 (3) | C6—C7 | 1.476 (3) |
O2—C15 | 1.419 (3) | C9—C14 | 1.378 (3) |
N1—C7 | 1.377 (3) | C9—C10 | 1.392 (3) |
N1—C8 | 1.386 (3) | C10—C11 | 1.374 (4) |
N1—H1 | 0.8600 | C11—C12 | 1.372 (4) |
N2—C8 | 1.331 (3) | C11—H11 | 0.9300 |
N2—C9 | 1.415 (3) | C12—C13 | 1.371 (4) |
N2—H2 | 0.8600 | C12—H12 | 0.9300 |
C1—C2 | 1.373 (3) | C13—C14 | 1.382 (4) |
C1—C6 | 1.394 (3) | C13—H13 | 0.9300 |
C1—H1A | 0.9300 | C14—H14 | 0.9300 |
C2—C3 | 1.386 (3) | C15—H15A | 0.9600 |
C2—H2A | 0.9300 | C15—H15B | 0.9600 |
C3—C4 | 1.386 (3) | C15—H15C | 0.9600 |
C4—C5 | 1.379 (3) | ||
C3—O2—C15 | 118.2 (2) | N2—C8—N1 | 115.6 (2) |
C7—N1—C8 | 129.5 (2) | N2—C8—S1 | 126.28 (18) |
C7—N1—H1 | 115.3 | N1—C8—S1 | 118.11 (16) |
C8—N1—H1 | 115.3 | C14—C9—C10 | 118.5 (2) |
C8—N2—C9 | 127.0 (2) | C14—C9—N2 | 122.1 (2) |
C8—N2—H2 | 116.5 | C10—C9—N2 | 119.3 (2) |
C9—N2—H2 | 116.5 | C11—C10—C9 | 120.8 (3) |
C2—C1—C6 | 120.5 (2) | C11—C10—Cl1 | 119.4 (2) |
C2—C1—H1A | 119.8 | C9—C10—Cl1 | 119.80 (19) |
C6—C1—H1A | 119.8 | C12—C11—C10 | 119.9 (3) |
C1—C2—C3 | 120.6 (2) | C12—C11—H11 | 120.0 |
C1—C2—H2A | 119.7 | C10—C11—H11 | 120.0 |
C3—C2—H2A | 119.7 | C13—C12—C11 | 120.2 (2) |
O2—C3—C2 | 116.0 (2) | C13—C12—H12 | 119.9 |
O2—C3—C4 | 124.2 (2) | C11—C12—H12 | 119.9 |
C2—C3—C4 | 119.8 (2) | C12—C13—C14 | 120.0 (3) |
C5—C4—C3 | 118.9 (2) | C12—C13—H13 | 120.0 |
C5—C4—H4 | 120.5 | C14—C13—H13 | 120.0 |
C3—C4—H4 | 120.5 | C9—C14—C13 | 120.7 (3) |
C4—C5—C6 | 122.1 (2) | C9—C14—H14 | 119.7 |
C4—C5—H5 | 118.9 | C13—C14—H14 | 119.7 |
C6—C5—H5 | 118.9 | O2—C15—H15A | 109.5 |
C5—C6—C1 | 118.0 (2) | O2—C15—H15B | 109.5 |
C5—C6—C7 | 117.7 (2) | H15A—C15—H15B | 109.5 |
C1—C6—C7 | 124.2 (2) | O2—C15—H15C | 109.5 |
O1—C7—N1 | 121.3 (2) | H15A—C15—H15C | 109.5 |
O1—C7—C6 | 121.6 (2) | H15B—C15—H15C | 109.5 |
N1—C7—C6 | 117.2 (2) | ||
C6—C1—C2—C3 | −0.4 (4) | C9—N2—C8—N1 | −179.3 (2) |
C15—O2—C3—C2 | 178.6 (3) | C9—N2—C8—S1 | 1.8 (4) |
C15—O2—C3—C4 | −1.2 (4) | C7—N1—C8—N2 | −1.6 (4) |
C1—C2—C3—O2 | −178.6 (2) | C7—N1—C8—S1 | 177.4 (2) |
C1—C2—C3—C4 | 1.1 (4) | C8—N2—C9—C14 | 46.2 (4) |
O2—C3—C4—C5 | 178.5 (2) | C8—N2—C9—C10 | −137.0 (3) |
C2—C3—C4—C5 | −1.2 (4) | C14—C9—C10—C11 | −0.6 (4) |
C3—C4—C5—C6 | 0.8 (4) | N2—C9—C10—C11 | −177.5 (3) |
C4—C5—C6—C1 | −0.1 (4) | C14—C9—C10—Cl1 | 178.1 (2) |
C4—C5—C6—C7 | −178.6 (2) | N2—C9—C10—Cl1 | 1.2 (3) |
C2—C1—C6—C5 | −0.1 (4) | C9—C10—C11—C12 | −0.7 (5) |
C2—C1—C6—C7 | 178.4 (2) | Cl1—C10—C11—C12 | −179.3 (2) |
C8—N1—C7—O1 | −1.1 (5) | C10—C11—C12—C13 | 0.8 (5) |
C8—N1—C7—C6 | 179.3 (2) | C11—C12—C13—C14 | 0.4 (5) |
C5—C6—C7—O1 | 11.0 (4) | C10—C9—C14—C13 | 1.7 (4) |
C1—C6—C7—O1 | −167.4 (3) | N2—C9—C14—C13 | 178.5 (2) |
C5—C6—C7—N1 | −169.4 (2) | C12—C13—C14—C9 | −1.6 (4) |
C1—C6—C7—N1 | 12.2 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O1 | 0.86 | 1.93 | 2.638 (3) | 138 |
C14—H14···S1 | 0.93 | 2.80 | 3.209 (3) | 107 |
C1—H1A···S1i | 0.93 | 2.78 | 3.666 (3) | 159 |
Symmetry code: (i) −x+1/2, y−1/2, −z+1/2. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register