Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807043541/wn2200sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807043541/wn2200Isup2.hkl |
CCDC reference: 667332
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.003 Å
- R factor = 0.037
- wR factor = 0.102
- Data-to-parameter ratio = 13.4
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 ....... ? PLAT150_ALERT_1_C Volume as Calculated Differs from that Given ... 3727.00 Ang-3 PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) 600 Ang. PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C16 PLAT431_ALERT_2_C Short Inter HL..A Contact Cl1 .. S1 .. 3.53 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 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 0 ALERT type 5 Informative message, check
Powdered ammonium thiocyanate (15 mmol), 5-chloro-3-methyl-1-phenylpyrazole-4-carbonyl chloride (10 mmol), PEG-400 (0.15 mmol) and acetone (25 ml) were placed in a dried round-bottomed flask containing a magnetic stirrer bar. The mixture was stirred at room temperature for 1 h, then 4-methylaniline (9.5 mmol) was added, and the mixture was stirred for 10 h. The mixture was poured into water (20 ml). The resulting solid was filtered, dried and recrystallized from DMF-EtOH to give N-(4-methylphenyl)-N'-(5-chloro-3-methyl-1-phenylpyrazol-4-yl- carbonyl)thiourea. Single crystals of the title compound were obtained by slow evaporation of a solution in DMF-EtOH (1:1, v/v).
H atoms bonded to N atoms were located in a difference map and refined with distance restraints of N—H = 0.83 (3) Å, and with Uiso(H) = 1.2Ueq(N). Other H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93–0.96 Å; Uiso(H) = xUeq(carrier atom) where x = 1.5 for methyl groups and 1.2 for Csp2.
In this paper, the synthesis and crystal structure of the title compound is reported. The molecular structure and the atom-numbering scheme are shown in Fig.1. The pyrazole ring makes dihedral angles of 74.3 (3)° and 2.9 (3)° with the C1—C6 ring and the C13—C18 rings, respectively; these two six-membered rings are twisted by 71.6 (3)° with respect to each other. However in the similar structure, 1-(3-methoxyphenyl)-3-(4-methylbenzoyl)thiourea (Saeed et al., 2007), the dihedral angle between the two phenyl ring planes is 48.3 (1)°. All bond lengths and angles are in the normal ranges (Saeed et al., 2007; Wang et al., 2007). The crystal packing of the title compound is stabilized by intramolcular N—H···O and intermolecular N—H···S hydrogen bonds.
For related literature, see: Saeed & Flörke (2007); Wang et al. (2007).
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).
C19H17ClN4OS | Dx = 1.372 Mg m−3 |
Mr = 384.88 | Melting point: 437 K |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 14.935 (6) Å | Cell parameters from 3035 reflections |
b = 16.321 (6) Å | θ = 2.2–25.9° |
c = 15.469 (6) Å | µ = 0.33 mm−1 |
β = 98.786 (6)° | T = 294 K |
V = 3727 (2) Å3 | Prism, colourless |
Z = 8 | 0.24 × 0.22 × 0.10 mm |
F(000) = 1600 |
Bruker SMART 1K CCD area-detector diffractometer | 3275 independent reflections |
Radiation source: fine-focus sealed tube | 2512 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
phi and ω scans | θmax = 25.0°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −17→13 |
Tmin = 0.924, Tmax = 0.968 | k = −19→16 |
7376 measured reflections | l = −18→18 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.037 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.102 | w = 1/[σ2(Fo2) + (0.0444P)2 + 3.1362P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.002 |
3275 reflections | Δρmax = 0.26 e Å−3 |
244 parameters | Δρmin = −0.29 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0135 (6) |
C19H17ClN4OS | V = 3727 (2) Å3 |
Mr = 384.88 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 14.935 (6) Å | µ = 0.33 mm−1 |
b = 16.321 (6) Å | T = 294 K |
c = 15.469 (6) Å | 0.24 × 0.22 × 0.10 mm |
β = 98.786 (6)° |
Bruker SMART 1K CCD area-detector diffractometer | 3275 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2512 reflections with I > 2σ(I) |
Tmin = 0.924, Tmax = 0.968 | Rint = 0.028 |
7376 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | 0 restraints |
wR(F2) = 0.102 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.26 e Å−3 |
3275 reflections | Δρmin = −0.29 e Å−3 |
244 parameters |
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. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.26808 (4) | 0.10959 (3) | 0.18875 (4) | 0.0489 (2) | |
S1 | 0.25725 (4) | 0.37690 (4) | 0.04136 (5) | 0.0548 (2) | |
O1 | 0.52013 (11) | 0.25072 (9) | 0.15254 (13) | 0.0601 (5) | |
N1 | 0.38841 (11) | 0.00224 (10) | 0.15040 (11) | 0.0368 (4) | |
N2 | 0.47254 (11) | −0.00682 (11) | 0.12675 (12) | 0.0416 (5) | |
N3 | 0.36918 (12) | 0.25941 (11) | 0.10169 (13) | 0.0435 (5) | |
H3A | 0.3265 (16) | 0.2329 (15) | 0.0743 (16) | 0.052* | |
N4 | 0.42555 (14) | 0.38937 (11) | 0.12986 (14) | 0.0505 (5) | |
H4A | 0.4725 (18) | 0.3629 (16) | 0.1476 (17) | 0.061* | |
C1 | 0.33371 (14) | −0.06761 (12) | 0.16252 (14) | 0.0362 (5) | |
C2 | 0.26236 (16) | −0.08688 (15) | 0.09905 (17) | 0.0514 (6) | |
H2 | 0.2502 | −0.0555 | 0.0484 | 0.062* | |
C3 | 0.20897 (16) | −0.15344 (15) | 0.11148 (19) | 0.0590 (7) | |
H3 | 0.1600 | −0.1668 | 0.0692 | 0.071* | |
C4 | 0.22750 (16) | −0.19991 (14) | 0.18540 (18) | 0.0530 (6) | |
H4 | 0.1914 | −0.2449 | 0.1932 | 0.064* | |
C5 | 0.29946 (17) | −0.18026 (14) | 0.24817 (17) | 0.0529 (6) | |
H5 | 0.3119 | −0.2120 | 0.2985 | 0.064* | |
C6 | 0.35346 (15) | −0.11362 (13) | 0.23706 (15) | 0.0435 (5) | |
H6 | 0.4024 | −0.1002 | 0.2794 | 0.052* | |
C7 | 0.59176 (15) | 0.08158 (16) | 0.08879 (18) | 0.0533 (6) | |
H7A | 0.6216 | 0.0298 | 0.0861 | 0.080* | |
H7B | 0.6283 | 0.1167 | 0.1297 | 0.080* | |
H7C | 0.5831 | 0.1066 | 0.0320 | 0.080* | |
C8 | 0.50222 (13) | 0.06866 (13) | 0.11763 (14) | 0.0375 (5) | |
C9 | 0.43742 (13) | 0.12760 (12) | 0.13398 (14) | 0.0355 (5) | |
C10 | 0.36644 (13) | 0.08160 (12) | 0.15463 (13) | 0.0345 (5) | |
C11 | 0.44734 (14) | 0.21691 (13) | 0.13126 (14) | 0.0397 (5) | |
C12 | 0.35583 (15) | 0.34383 (13) | 0.09374 (15) | 0.0418 (5) | |
C13 | 0.43399 (15) | 0.47650 (13) | 0.12661 (15) | 0.0456 (6) | |
C14 | 0.51457 (17) | 0.50783 (15) | 0.1089 (2) | 0.0638 (8) | |
H14 | 0.5615 | 0.4727 | 0.1007 | 0.077* | |
C15 | 0.52592 (18) | 0.59178 (16) | 0.1034 (2) | 0.0632 (7) | |
H15 | 0.5807 | 0.6123 | 0.0911 | 0.076* | |
C16 | 0.45840 (17) | 0.64529 (14) | 0.11565 (16) | 0.0499 (6) | |
C17 | 0.37896 (19) | 0.61242 (15) | 0.13533 (19) | 0.0615 (7) | |
H17 | 0.3325 | 0.6476 | 0.1450 | 0.074* | |
C18 | 0.36606 (18) | 0.52902 (15) | 0.14119 (18) | 0.0586 (7) | |
H18 | 0.3118 | 0.5086 | 0.1549 | 0.070* | |
C19 | 0.4709 (2) | 0.73671 (15) | 0.1069 (2) | 0.0743 (9) | |
H19A | 0.4915 | 0.7598 | 0.1635 | 0.111* | |
H19B | 0.4141 | 0.7613 | 0.0827 | 0.111* | |
H19C | 0.5148 | 0.7471 | 0.0690 | 0.111* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0403 (3) | 0.0417 (3) | 0.0680 (4) | 0.0026 (2) | 0.0185 (3) | −0.0021 (3) |
S1 | 0.0537 (4) | 0.0364 (3) | 0.0676 (4) | 0.0055 (3) | −0.0116 (3) | 0.0025 (3) |
O1 | 0.0356 (9) | 0.0367 (9) | 0.1031 (15) | −0.0072 (7) | −0.0047 (9) | 0.0049 (9) |
N1 | 0.0299 (9) | 0.0296 (9) | 0.0509 (11) | 0.0002 (7) | 0.0065 (8) | 0.0045 (8) |
N2 | 0.0306 (9) | 0.0356 (10) | 0.0586 (12) | 0.0026 (8) | 0.0071 (8) | 0.0041 (8) |
N3 | 0.0365 (10) | 0.0298 (10) | 0.0601 (13) | −0.0037 (8) | −0.0063 (9) | 0.0035 (9) |
N4 | 0.0461 (12) | 0.0318 (11) | 0.0691 (14) | −0.0025 (9) | −0.0054 (10) | 0.0013 (9) |
C1 | 0.0337 (11) | 0.0270 (10) | 0.0480 (13) | −0.0008 (8) | 0.0068 (9) | 0.0008 (9) |
C2 | 0.0478 (14) | 0.0456 (14) | 0.0570 (15) | −0.0052 (11) | −0.0043 (12) | 0.0107 (11) |
C3 | 0.0436 (14) | 0.0480 (15) | 0.0786 (19) | −0.0120 (11) | −0.0125 (13) | 0.0035 (13) |
C4 | 0.0434 (13) | 0.0352 (13) | 0.0799 (18) | −0.0081 (10) | 0.0080 (12) | 0.0083 (12) |
C5 | 0.0569 (15) | 0.0416 (13) | 0.0593 (16) | −0.0058 (11) | 0.0057 (12) | 0.0148 (11) |
C6 | 0.0431 (12) | 0.0369 (12) | 0.0482 (14) | −0.0051 (10) | 0.0002 (10) | 0.0032 (10) |
C7 | 0.0370 (12) | 0.0513 (14) | 0.0735 (18) | −0.0021 (11) | 0.0142 (12) | 0.0003 (13) |
C8 | 0.0295 (10) | 0.0364 (12) | 0.0453 (13) | −0.0008 (9) | 0.0017 (9) | 0.0040 (9) |
C9 | 0.0304 (11) | 0.0323 (11) | 0.0420 (12) | −0.0029 (9) | −0.0005 (9) | 0.0043 (9) |
C10 | 0.0302 (10) | 0.0314 (11) | 0.0411 (12) | 0.0019 (9) | 0.0032 (9) | 0.0010 (9) |
C11 | 0.0347 (12) | 0.0348 (12) | 0.0485 (13) | −0.0027 (9) | 0.0030 (10) | 0.0029 (10) |
C12 | 0.0478 (13) | 0.0313 (11) | 0.0455 (13) | −0.0015 (10) | 0.0041 (10) | 0.0029 (10) |
C13 | 0.0492 (14) | 0.0312 (12) | 0.0535 (14) | −0.0044 (10) | −0.0018 (11) | −0.0024 (10) |
C14 | 0.0417 (14) | 0.0396 (14) | 0.107 (2) | 0.0002 (11) | 0.0025 (14) | −0.0073 (14) |
C15 | 0.0478 (15) | 0.0444 (15) | 0.097 (2) | −0.0118 (12) | 0.0092 (14) | −0.0041 (14) |
C16 | 0.0573 (15) | 0.0365 (13) | 0.0533 (15) | −0.0059 (11) | 0.0002 (12) | −0.0042 (11) |
C17 | 0.0652 (17) | 0.0389 (14) | 0.085 (2) | 0.0006 (12) | 0.0254 (15) | −0.0131 (13) |
C18 | 0.0616 (16) | 0.0401 (14) | 0.0791 (19) | −0.0066 (12) | 0.0266 (14) | −0.0096 (13) |
C19 | 0.087 (2) | 0.0382 (15) | 0.097 (2) | −0.0115 (14) | 0.0136 (18) | −0.0058 (14) |
Cl1—C10 | 1.698 (2) | C6—H6 | 0.9300 |
S1—C12 | 1.659 (2) | C7—C8 | 1.488 (3) |
O1—C11 | 1.219 (2) | C7—H7A | 0.9600 |
N1—C10 | 1.340 (3) | C7—H7B | 0.9600 |
N1—N2 | 1.369 (2) | C7—H7C | 0.9600 |
N1—C1 | 1.431 (3) | C8—C9 | 1.415 (3) |
N2—C8 | 1.324 (3) | C9—C10 | 1.376 (3) |
N3—C11 | 1.375 (3) | C9—C11 | 1.466 (3) |
N3—C12 | 1.395 (3) | C13—C18 | 1.373 (3) |
N3—H3A | 0.83 (2) | C13—C14 | 1.373 (3) |
N4—C12 | 1.331 (3) | C14—C15 | 1.385 (4) |
N4—C13 | 1.429 (3) | C14—H14 | 0.9300 |
N4—H4A | 0.83 (3) | C15—C16 | 1.369 (4) |
C1—C6 | 1.370 (3) | C15—H15 | 0.9300 |
C1—C2 | 1.371 (3) | C16—C17 | 1.378 (4) |
C2—C3 | 1.378 (3) | C16—C19 | 1.512 (3) |
C2—H2 | 0.9300 | C17—C18 | 1.380 (3) |
C3—C4 | 1.365 (4) | C17—H17 | 0.9300 |
C3—H3 | 0.9300 | C18—H18 | 0.9300 |
C4—C5 | 1.372 (3) | C19—H19A | 0.9600 |
C4—H4 | 0.9300 | C19—H19B | 0.9600 |
C5—C6 | 1.380 (3) | C19—H19C | 0.9600 |
C5—H5 | 0.9300 | ||
C10—N1—N2 | 111.03 (16) | C10—C9—C8 | 104.05 (18) |
C10—N1—C1 | 127.92 (17) | C10—C9—C11 | 129.34 (19) |
N2—N1—C1 | 120.95 (16) | C8—C9—C11 | 126.59 (19) |
C8—N2—N1 | 105.29 (16) | N1—C10—C9 | 108.24 (18) |
C11—N3—C12 | 129.08 (19) | N1—C10—Cl1 | 120.34 (15) |
C11—N3—H3A | 116.9 (17) | C9—C10—Cl1 | 131.25 (16) |
C12—N3—H3A | 112.4 (17) | O1—C11—N3 | 122.6 (2) |
C12—N4—C13 | 127.5 (2) | O1—C11—C9 | 122.16 (19) |
C12—N4—H4A | 114.4 (19) | N3—C11—C9 | 115.26 (18) |
C13—N4—H4A | 116.9 (19) | N4—C12—N3 | 114.99 (19) |
C6—C1—C2 | 121.4 (2) | N4—C12—S1 | 127.06 (17) |
C6—C1—N1 | 119.54 (19) | N3—C12—S1 | 117.95 (16) |
C2—C1—N1 | 119.06 (19) | C18—C13—C14 | 119.5 (2) |
C1—C2—C3 | 118.9 (2) | C18—C13—N4 | 123.0 (2) |
C1—C2—H2 | 120.5 | C14—C13—N4 | 117.5 (2) |
C3—C2—H2 | 120.5 | C13—C14—C15 | 120.0 (2) |
C4—C3—C2 | 120.5 (2) | C13—C14—H14 | 120.0 |
C4—C3—H3 | 119.8 | C15—C14—H14 | 120.0 |
C2—C3—H3 | 119.8 | C16—C15—C14 | 121.5 (2) |
C3—C4—C5 | 120.0 (2) | C16—C15—H15 | 119.2 |
C3—C4—H4 | 120.0 | C14—C15—H15 | 119.2 |
C5—C4—H4 | 120.0 | C15—C16—C17 | 117.4 (2) |
C4—C5—C6 | 120.4 (2) | C15—C16—C19 | 120.9 (2) |
C4—C5—H5 | 119.8 | C17—C16—C19 | 121.7 (2) |
C6—C5—H5 | 119.8 | C16—C17—C18 | 122.2 (2) |
C1—C6—C5 | 118.8 (2) | C16—C17—H17 | 118.9 |
C1—C6—H6 | 120.6 | C18—C17—H17 | 118.9 |
C5—C6—H6 | 120.6 | C13—C18—C17 | 119.4 (2) |
C8—C7—H7A | 109.5 | C13—C18—H18 | 120.3 |
C8—C7—H7B | 109.5 | C17—C18—H18 | 120.3 |
H7A—C7—H7B | 109.5 | C16—C19—H19A | 109.5 |
C8—C7—H7C | 109.5 | C16—C19—H19B | 109.5 |
H7A—C7—H7C | 109.5 | H19A—C19—H19B | 109.5 |
H7B—C7—H7C | 109.5 | C16—C19—H19C | 109.5 |
N2—C8—C9 | 111.37 (18) | H19A—C19—H19C | 109.5 |
N2—C8—C7 | 119.65 (19) | H19B—C19—H19C | 109.5 |
C9—C8—C7 | 128.9 (2) | ||
C10—N1—N2—C8 | 0.8 (2) | C11—C9—C10—N1 | −178.5 (2) |
C1—N1—N2—C8 | 177.37 (18) | C8—C9—C10—Cl1 | 175.06 (17) |
C10—N1—C1—C6 | −107.7 (3) | C11—C9—C10—Cl1 | −3.3 (4) |
N2—N1—C1—C6 | 76.3 (3) | C12—N3—C11—O1 | −3.0 (4) |
C10—N1—C1—C2 | 72.2 (3) | C12—N3—C11—C9 | 178.1 (2) |
N2—N1—C1—C2 | −103.8 (2) | C10—C9—C11—O1 | 144.7 (2) |
C6—C1—C2—C3 | 0.8 (4) | C8—C9—C11—O1 | −33.4 (4) |
N1—C1—C2—C3 | −179.0 (2) | C10—C9—C11—N3 | −36.4 (3) |
C1—C2—C3—C4 | −0.7 (4) | C8—C9—C11—N3 | 145.5 (2) |
C2—C3—C4—C5 | 0.3 (4) | C13—N4—C12—N3 | 175.1 (2) |
C3—C4—C5—C6 | 0.0 (4) | C13—N4—C12—S1 | −4.7 (4) |
C2—C1—C6—C5 | −0.5 (4) | C11—N3—C12—N4 | −9.3 (4) |
N1—C1—C6—C5 | 179.3 (2) | C11—N3—C12—S1 | 170.60 (19) |
C4—C5—C6—C1 | 0.1 (4) | C12—N4—C13—C18 | 45.8 (4) |
N1—N2—C8—C9 | −0.8 (2) | C12—N4—C13—C14 | −134.9 (3) |
N1—N2—C8—C7 | −177.85 (19) | C18—C13—C14—C15 | −1.9 (4) |
N2—C8—C9—C10 | 0.6 (2) | N4—C13—C14—C15 | 178.8 (2) |
C7—C8—C9—C10 | 177.3 (2) | C13—C14—C15—C16 | 0.3 (4) |
N2—C8—C9—C11 | 179.1 (2) | C14—C15—C16—C17 | 1.2 (4) |
C7—C8—C9—C11 | −4.3 (4) | C14—C15—C16—C19 | −178.3 (3) |
N2—N1—C10—C9 | −0.4 (2) | C15—C16—C17—C18 | −1.2 (4) |
C1—N1—C10—C9 | −176.71 (19) | C19—C16—C17—C18 | 178.3 (3) |
N2—N1—C10—Cl1 | −176.19 (14) | C14—C13—C18—C17 | 1.9 (4) |
C1—N1—C10—Cl1 | 7.5 (3) | N4—C13—C18—C17 | −178.9 (2) |
C8—C9—C10—N1 | −0.1 (2) | C16—C17—C18—C13 | −0.3 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···S1i | 0.83 (2) | 2.70 (2) | 3.484 (2) | 158 (2) |
N4—H4A···O1 | 0.83 (3) | 1.96 (3) | 2.662 (3) | 141 (2) |
Symmetry code: (i) −x+1/2, −y+1/2, −z. |
Experimental details
Crystal data | |
Chemical formula | C19H17ClN4OS |
Mr | 384.88 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 294 |
a, b, c (Å) | 14.935 (6), 16.321 (6), 15.469 (6) |
β (°) | 98.786 (6) |
V (Å3) | 3727 (2) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.33 |
Crystal size (mm) | 0.24 × 0.22 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART 1K CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.924, 0.968 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7376, 3275, 2512 |
Rint | 0.028 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.102, 1.03 |
No. of reflections | 3275 |
No. of parameters | 244 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.26, −0.29 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···S1i | 0.83 (2) | 2.70 (2) | 3.484 (2) | 158 (2) |
N4—H4A···O1 | 0.83 (3) | 1.96 (3) | 2.662 (3) | 141 (2) |
Symmetry code: (i) −x+1/2, −y+1/2, −z. |
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In this paper, the synthesis and crystal structure of the title compound is reported. The molecular structure and the atom-numbering scheme are shown in Fig.1. The pyrazole ring makes dihedral angles of 74.3 (3)° and 2.9 (3)° with the C1—C6 ring and the C13—C18 rings, respectively; these two six-membered rings are twisted by 71.6 (3)° with respect to each other. However in the similar structure, 1-(3-methoxyphenyl)-3-(4-methylbenzoyl)thiourea (Saeed et al., 2007), the dihedral angle between the two phenyl ring planes is 48.3 (1)°. All bond lengths and angles are in the normal ranges (Saeed et al., 2007; Wang et al., 2007). The crystal packing of the title compound is stabilized by intramolcular N—H···O and intermolecular N—H···S hydrogen bonds.