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organic compounds
In the molecule of the title compound, C14H11ClN2OS, the dihedral angle between the o-chlorophenyl ring and the central carbonylthiourea fragment is 29.36 (8)°. There is an intramolecular N—H
Cl/O bifurcated hydrogen bond. The molecules are linked by N—HS hydrogen bonds, forming dimers which are arranged parallel to (100).
Cl/O bifurcated hydrogen bond. The molecules are linked by N—HS hydrogen bonds, forming dimers which are arranged parallel to (100).Supporting information
 | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804017544/ob6388sup1.cif |
 | Structure factor file (CIF format) https://doi.org/10.1107/S1600536804017544/ob6388Isup2.hkl |
CCDC reference: 248841
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean
![[sigma]](//journals.iucr.org/logos/entities/sigma_rmgif.gif)
(C-C) = 0.003 Å - R factor = 0.043
- wR factor = 0.113
- Data-to-parameter ratio = 17.7
![[sigma]](http://journals.iucr.org/logos/entities/sigma_rmgif.gif){kind=small}
(C-C) = 0.003 ÅcheckCIF/PLATON results
No syntax errors found
Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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
Alert level C
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; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
N'-Benzoyl-N-(o-cholorophenyl)thiourea top
Crystal data top
| C14H11ClN2OS | F(000) = 600 |
| Mr = 290.76 | Dx = 1.449 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| a = 8.1435 (8) Å | Cell parameters from 2207 reflections |
| b = 12.3788 (13) Å | θ = 2.3–27.5° |
| c = 13.2782 (14) Å | µ = 0.44 mm−1 |
| β = 95.332 (2)° | T = 293 K |
| V = 1332.7 (2) Å3 | Block, colourless |
| Z = 4 | 0.39 × 0.35 × 0.34 mm |
Data collection top
| Bruker SMART APEX CCD area-detector diffractometer | 3039 independent reflections |
| Radiation source: fine-focus sealed tube | 2336 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.020 |
| Detector resolution: 83.66 pixels mm-1 | θmax = 27.5°, θmin = 2.3° |
| ω scans | h = −10→10 |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −15→16 |
| Tmin = 0.849, Tmax = 0.866 | l = −17→12 |
| 7955 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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.113 | H-atom parameters constrained |
| S = 1.02 | w = 1/[σ2(Fo2) + (0.0497P)2 + 0.3301P] where P = (Fo2 + 2Fc2)/3 |
| 3039 reflections | (Δ/σ)max < 0.001 |
| 172 parameters | Δρmax = 0.29 e Å−3 |
| 0 restraints | Δρmin = −0.20 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
| x | y | z | Uiso*/Ueq | ||
| S1 | 0.23411 (8) | 0.46492 (4) | 0.06478 (5) | 0.0680 (2) | |
| O1 | 0.02818 (17) | 0.15698 (10) | −0.08225 (10) | 0.0545 (4) | |
| N1 | 0.0585 (2) | 0.33750 (12) | −0.05882 (12) | 0.0517 (4) | |
| H1A | 0.0246 | 0.3986 | −0.0836 | 0.062* | |
| N2 | 0.19520 (18) | 0.24978 (11) | 0.07583 (11) | 0.0451 (4) | |
| H2A | 0.1523 | 0.1940 | 0.0450 | 0.054* | |
| C5 | −0.1775 (3) | 0.18870 (17) | −0.26140 (15) | 0.0569 (5) | |
| H5 | −0.1840 | 0.1223 | −0.2292 | 0.068* | |
| C4 | −0.2592 (3) | 0.2043 (2) | −0.35639 (17) | 0.0678 (6) | |
| H4 | −0.3211 | 0.1484 | −0.3876 | 0.081* | |
| C3 | −0.2495 (3) | 0.3012 (2) | −0.40465 (17) | 0.0662 (6) | |
| H3 | −0.3046 | 0.3111 | −0.4685 | 0.079* | |
| C2 | −0.1584 (3) | 0.38399 (18) | −0.35891 (16) | 0.0618 (6) | |
| H2 | −0.1512 | 0.4498 | −0.3920 | 0.074* | |
| C1 | −0.0774 (2) | 0.36954 (16) | −0.26383 (14) | 0.0515 (5) | |
| H1 | −0.0166 | 0.4260 | −0.2329 | 0.062* | |
| C6 | −0.0863 (2) | 0.27172 (15) | −0.21423 (14) | 0.0446 (4) | |
| C7 | 0.0026 (2) | 0.24864 (14) | −0.11327 (14) | 0.0444 (4) | |
| C8 | 0.1617 (2) | 0.34384 (14) | 0.03045 (14) | 0.0469 (4) | |
| C9 | 0.2914 (2) | 0.22849 (14) | 0.16777 (13) | 0.0417 (4) | |
| C14 | 0.3118 (2) | 0.30061 (17) | 0.24792 (14) | 0.0526 (5) | |
| H14 | 0.2641 | 0.3688 | 0.2417 | 0.063* | |
| C13 | 0.4021 (3) | 0.27197 (19) | 0.33648 (16) | 0.0601 (5) | |
| H13 | 0.4165 | 0.3216 | 0.3892 | 0.072* | |
| C12 | 0.4715 (3) | 0.17088 (19) | 0.34822 (16) | 0.0624 (6) | |
| H12 | 0.5322 | 0.1522 | 0.4085 | 0.075* | |
| C11 | 0.4506 (3) | 0.09781 (18) | 0.27039 (16) | 0.0587 (5) | |
| H11 | 0.4963 | 0.0291 | 0.2778 | 0.070* | |
| C10 | 0.3616 (2) | 0.12699 (15) | 0.18127 (14) | 0.0471 (4) | |
| Cl1 | 0.33880 (8) | 0.03377 (4) | 0.08345 (4) | 0.0718 (2) |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| S1 | 0.0842 (4) | 0.0398 (3) | 0.0728 (4) | −0.0031 (2) | −0.0304 (3) | −0.0030 (2) |
| O1 | 0.0727 (9) | 0.0409 (7) | 0.0472 (8) | −0.0038 (6) | −0.0089 (7) | 0.0023 (6) |
| N1 | 0.0632 (10) | 0.0380 (8) | 0.0494 (9) | 0.0057 (7) | −0.0191 (8) | −0.0018 (7) |
| N2 | 0.0538 (8) | 0.0380 (8) | 0.0410 (8) | 0.0009 (6) | −0.0090 (7) | −0.0013 (6) |
| C5 | 0.0639 (12) | 0.0541 (12) | 0.0507 (11) | −0.0065 (9) | −0.0052 (10) | −0.0040 (9) |
| C4 | 0.0685 (14) | 0.0752 (15) | 0.0557 (13) | −0.0090 (11) | −0.0148 (11) | −0.0127 (12) |
| C3 | 0.0688 (14) | 0.0830 (16) | 0.0440 (11) | 0.0096 (12) | −0.0092 (10) | 0.0000 (11) |
| C2 | 0.0723 (14) | 0.0632 (13) | 0.0481 (12) | 0.0087 (11) | −0.0037 (10) | 0.0070 (10) |
| C1 | 0.0570 (11) | 0.0511 (11) | 0.0451 (10) | 0.0013 (9) | −0.0019 (9) | −0.0015 (9) |
| C6 | 0.0440 (9) | 0.0477 (10) | 0.0409 (9) | 0.0035 (8) | −0.0021 (7) | −0.0034 (8) |
| C7 | 0.0463 (9) | 0.0433 (10) | 0.0426 (10) | −0.0002 (8) | −0.0008 (8) | −0.0029 (8) |
| C8 | 0.0493 (10) | 0.0427 (10) | 0.0462 (10) | 0.0054 (8) | −0.0085 (8) | −0.0037 (8) |
| C9 | 0.0399 (8) | 0.0463 (9) | 0.0379 (9) | −0.0008 (7) | −0.0021 (7) | 0.0020 (8) |
| C14 | 0.0559 (11) | 0.0540 (11) | 0.0467 (11) | 0.0034 (9) | −0.0012 (9) | −0.0047 (9) |
| C13 | 0.0630 (12) | 0.0727 (14) | 0.0434 (11) | −0.0047 (11) | −0.0019 (9) | −0.0101 (10) |
| C12 | 0.0605 (12) | 0.0778 (15) | 0.0457 (11) | 0.0032 (11) | −0.0120 (10) | 0.0050 (11) |
| C11 | 0.0625 (12) | 0.0603 (13) | 0.0513 (12) | 0.0097 (10) | −0.0061 (10) | 0.0093 (10) |
| C10 | 0.0521 (10) | 0.0459 (10) | 0.0422 (10) | 0.0020 (8) | −0.0011 (8) | 0.0012 (8) |
| Cl1 | 0.1107 (5) | 0.0455 (3) | 0.0553 (3) | 0.0155 (3) | −0.0138 (3) | −0.0050 (2) |
Geometric parameters (Å, º) top
| S1—C8 | 1.6588 (19) | C2—H2 | 0.9300 |
| O1—C7 | 1.218 (2) | C1—C6 | 1.383 (3) |
| N1—C7 | 1.371 (2) | C1—H1 | 0.9300 |
| N1—C8 | 1.390 (2) | C6—C7 | 1.491 (3) |
| N1—H1A | 0.8600 | C9—C10 | 1.385 (2) |
| N2—C8 | 1.328 (2) | C9—C14 | 1.387 (3) |
| N2—C9 | 1.413 (2) | C14—C13 | 1.374 (3) |
| N2—H2A | 0.8600 | C14—H14 | 0.9300 |
| C5—C6 | 1.383 (3) | C13—C12 | 1.376 (3) |
| C5—C4 | 1.384 (3) | C13—H13 | 0.9300 |
| C5—H5 | 0.9300 | C12—C11 | 1.372 (3) |
| C4—C3 | 1.366 (3) | C12—H12 | 0.9300 |
| C4—H4 | 0.9300 | C11—C10 | 1.377 (3) |
| C3—C2 | 1.374 (3) | C11—H11 | 0.9300 |
| C3—H3 | 0.9300 | C10—Cl1 | 1.7344 (19) |
| C2—C1 | 1.380 (3) | ||
| C7—N1—C8 | 129.78 (16) | O1—C7—N1 | 122.09 (16) |
| C7—N1—H1A | 115.1 | O1—C7—C6 | 122.40 (16) |
| C8—N1—H1A | 115.1 | N1—C7—C6 | 115.48 (16) |
| C8—N2—C9 | 129.03 (15) | N2—C8—N1 | 114.83 (16) |
| C8—N2—H2A | 115.5 | N2—C8—S1 | 127.95 (14) |
| C9—N2—H2A | 115.5 | N1—C8—S1 | 117.17 (13) |
| C6—C5—C4 | 120.1 (2) | C10—C9—C14 | 117.77 (16) |
| C6—C5—H5 | 119.9 | C10—C9—N2 | 118.04 (16) |
| C4—C5—H5 | 119.9 | C14—C9—N2 | 124.06 (16) |
| C3—C4—C5 | 120.4 (2) | C13—C14—C9 | 120.46 (19) |
| C3—C4—H4 | 119.8 | C13—C14—H14 | 119.8 |
| C5—C4—H4 | 119.8 | C9—C14—H14 | 119.8 |
| C4—C3—C2 | 120.0 (2) | C14—C13—C12 | 120.9 (2) |
| C4—C3—H3 | 120.0 | C14—C13—H13 | 119.6 |
| C2—C3—H3 | 120.0 | C12—C13—H13 | 119.6 |
| C3—C2—C1 | 120.0 (2) | C11—C12—C13 | 119.57 (19) |
| C3—C2—H2 | 120.0 | C11—C12—H12 | 120.2 |
| C1—C2—H2 | 120.0 | C13—C12—H12 | 120.2 |
| C2—C1—C6 | 120.49 (19) | C12—C11—C10 | 119.5 (2) |
| C2—C1—H1 | 119.8 | C12—C11—H11 | 120.2 |
| C6—C1—H1 | 119.8 | C10—C11—H11 | 120.2 |
| C1—C6—C5 | 118.96 (17) | C11—C10—C9 | 121.80 (18) |
| C1—C6—C7 | 123.60 (16) | C11—C10—Cl1 | 118.70 (15) |
| C5—C6—C7 | 117.40 (17) | C9—C10—Cl1 | 119.50 (14) |
| C6—C5—C4—C3 | 0.5 (3) | C7—N1—C8—N2 | −8.9 (3) |
| C5—C4—C3—C2 | 0.0 (4) | C7—N1—C8—S1 | 168.51 (17) |
| C4—C3—C2—C1 | −0.4 (3) | C8—N2—C9—C10 | −155.35 (19) |
| C3—C2—C1—C6 | 0.5 (3) | C8—N2—C9—C14 | 28.8 (3) |
| C2—C1—C6—C5 | 0.0 (3) | C10—C9—C14—C13 | 1.4 (3) |
| C2—C1—C6—C7 | 177.64 (19) | N2—C9—C14—C13 | 177.32 (18) |
| C4—C5—C6—C1 | −0.4 (3) | C9—C14—C13—C12 | −1.2 (3) |
| C4—C5—C6—C7 | −178.27 (19) | C14—C13—C12—C11 | 0.2 (3) |
| C8—N1—C7—O1 | 7.0 (3) | C13—C12—C11—C10 | 0.6 (3) |
| C8—N1—C7—C6 | −171.04 (18) | C12—C11—C10—C9 | −0.3 (3) |
| C1—C6—C7—O1 | −160.94 (19) | C12—C11—C10—Cl1 | 179.30 (17) |
| C5—C6—C7—O1 | 16.8 (3) | C14—C9—C10—C11 | −0.7 (3) |
| C1—C6—C7—N1 | 17.0 (3) | N2—C9—C10—C11 | −176.87 (18) |
| C5—C6—C7—N1 | −165.23 (17) | C14—C9—C10—Cl1 | 179.72 (15) |
| C9—N2—C8—N1 | −178.33 (17) | N2—C9—C10—Cl1 | 3.6 (2) |
| C9—N2—C8—S1 | 4.6 (3) |
Hydrogen-bond geometry (Å, º) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1A···S1i | 0.86 | 2.73 | 3.4105 (17) | 137 |
| N2—H2A···Cl1 | 0.86 | 2.52 | 2.9165 (15) | 109 |
| N2—H2A···O1 | 0.86 | 1.94 | 2.654 (2) | 139 |
| C14—H14···S1 | 0.93 | 2.62 | 3.188 (2) | 120 |
| Symmetry code: (i) −x, −y+1, −z. |
