Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807035179/si2028sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807035179/si2028Isup2.hkl |
CCDC reference: 657831
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.005 Å
- R factor = 0.063
- wR factor = 0.131
- Data-to-parameter ratio = 13.8
checkCIF/PLATON results
No syntax errors found
Alert level C REFLT03_ALERT_3_C Reflection count < 95% complete From the CIF: _diffrn_reflns_theta_max 26.00 From the CIF: _diffrn_reflns_theta_full 26.00 From the CIF: _reflns_number_total 3219 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 3404 Completeness (_total/calc) 94.57% PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.95 PLAT230_ALERT_2_C Hirshfeld Test Diff for Cl1 - C16 .. 6.92 su PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 5 PLAT420_ALERT_2_C D-H Without Acceptor N1 - H1A ... ?
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 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 4 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
A solution of 2-chloroaniline (0.63 g, 2.5 mmol) in 20 ml acetone was added dropwise to a two-necked round-bottomed flask containing an equimolar solution of biphenylcarbomoylisothiocyanate (0.60 g, 2.5 mmol) in 20 ml of acetone. The mixture was refluxed for about 3 h. The light yellow solution was filtered and allowed to evaporate at room temperature. Some colourless crystals were obtained after five days of evaporation (yield 0.71 g, 85%).
H atoms on C were positioned geometrically with C—H 0.93, 0.96 and 0.97 Å, for aromatic, methlylene and methyl H atoms respectively, constrained to ride on their parent atoms with Uiso(H)= 1.2Ueq(C). The hydrogen atom attached to the N atom were located from the difference map and refined isotropically.
Many aroylthiourea compounds reported so far are based on a benzene group. The title compound, (I), is also an aroylthiourea derivative but having a biphenyl group (Fig.1). The molecule maintains the trans-cis configuration with respect to the position of the biphenylcarbonyl and chlorobenzene groups about the thiono sulfur atom across their C14—N1 and C14—N2 bonds, respectively. The biphenyl fragment is not planar with C1—C6—C7—C12 and C5—C6—C7—C8 torsion angles of -18.9 (5) and -21.2 (5)° respectively. The bond lengths and angles are in normal ranges (Allen et al., 1987) and close to those observed in (II) (Yusof & Yamin, 2004) and (III) (Shoukat et al., 2007). The benzene C7—C12, the carbonyl-thiourea C13/O1/N1/C14/S1/N2 and the chlorobenzene Cl1/C15—C20 fragments are each planar with maximum deviation of 0.026 (3)Å for N1 atom from the least squares plane of the carbonyl-thiourea moiety. The central carbonyl-thiourea moiety makes dihedral angles with the C7—C12 benzene ring and chlorobenzene fragment of 24.39 (13) and 61.63 (10)°, respectively. There is an N2—H2A···O1 intramolecular hydrogen bond (D—H= 0.863 (12), H···A= 1.882 (18) D···A= 2.619 (4)Å and D—H···A =142 (3)°) formimg a pseudo six-membered ring [C13—N1—C14—N2—H2A···O1]. The crystal packing is stabilized by weak van der Waals and π···π interactions, between the benzene (C7—C12)i rings ((i): 1 - x, -y, -z) with the distance between the centroids of 3.629 (2) Å.
Many N-aroyl-N'(chlorophenyl)thiourea compounds, such as N-benzoyl-N'-(2-chlorophenyl)thiourea (Yusof & Yamin, 2004) and N-pivaloyl-N'-(2-chlorophenyl)thiourea (Shoukat et al., 2007), possess a trans–cis configuration with respect to the position of the carbomoyl and chlorophenyl groups against the thiono S atom about their thiourea C—N bonds, respectively.
For bond-length data, see: Allen et al. (1987).
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
Fig. 1. Molecular structure of compound, (1), with displacement ellipsoid drawn at the 50% probablity level. The dashed line indicates the intramolecular hydrogen bond. |
C20H15ClN2OS | F(000) = 760 |
Mr = 366.85 | Dx = 1.406 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 993 reflections |
a = 9.2448 (14) Å | θ = 1.5–26.0° |
b = 7.2284 (11) Å | µ = 0.35 mm−1 |
c = 25.934 (4) Å | T = 298 K |
β = 90.295 (3)° | Slab, colourless |
V = 1733.0 (5) Å3 | 0.50 × 0.30 × 0.07 mm |
Z = 4 |
Bruker SMART APEX CCD area-detector diffractometer | 3219 independent reflections |
Radiation source: fine-focus sealed tube | 1742 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.064 |
Detector resolution: 83.66 pixels mm-1 | θmax = 26.0°, θmin = 1.5° |
ω scans | h = −11→10 |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | k = −8→8 |
Tmin = 0.844, Tmax = 0.975 | l = −29→31 |
8945 measured reflections |
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)] = 0.063 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.131 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0507P)2 + 0.1441P] where P = (Fo2 + 2Fc2)/3 |
3219 reflections | (Δ/σ)max < 0.001 |
234 parameters | Δρmax = 0.17 e Å−3 |
2 restraints | Δρmin = −0.17 e Å−3 |
C20H15ClN2OS | V = 1733.0 (5) Å3 |
Mr = 366.85 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 9.2448 (14) Å | µ = 0.35 mm−1 |
b = 7.2284 (11) Å | T = 298 K |
c = 25.934 (4) Å | 0.50 × 0.30 × 0.07 mm |
β = 90.295 (3)° |
Bruker SMART APEX CCD area-detector diffractometer | 3219 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | 1742 reflections with I > 2σ(I) |
Tmin = 0.844, Tmax = 0.975 | Rint = 0.064 |
8945 measured reflections |
R[F2 > 2σ(F2)] = 0.063 | 2 restraints |
wR(F2) = 0.131 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Δρmax = 0.17 e Å−3 |
3219 reflections | Δρmin = −0.17 e Å−3 |
234 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 | 1.27749 (11) | 0.44805 (15) | 0.13364 (4) | 0.0817 (4) | |
S1 | 0.88704 (10) | 0.09939 (17) | 0.21077 (4) | 0.0781 (4) | |
O1 | 0.9742 (3) | 0.1787 (4) | 0.04062 (9) | 0.0664 (8) | |
N1 | 0.8363 (3) | 0.1431 (4) | 0.11180 (11) | 0.0503 (7) | |
H1A | 0.7484 (15) | 0.138 (5) | 0.1217 (12) | 0.071 (12)* | |
N2 | 1.0760 (3) | 0.1311 (4) | 0.13409 (11) | 0.0523 (8) | |
H2A | 1.084 (3) | 0.143 (4) | 0.1011 (4) | 0.051 (10)* | |
C1 | 0.3650 (4) | 0.3033 (5) | −0.12193 (13) | 0.0567 (10) | |
H1B | 0.4552 | 0.2864 | −0.1370 | 0.068* | |
C2 | 0.2491 (4) | 0.3507 (6) | −0.15248 (14) | 0.0695 (11) | |
H2B | 0.2623 | 0.3679 | −0.1877 | 0.083* | |
C3 | 0.1151 (4) | 0.3727 (5) | −0.13193 (15) | 0.0640 (10) | |
H3A | 0.0369 | 0.4040 | −0.1528 | 0.077* | |
C4 | 0.0972 (4) | 0.3481 (5) | −0.08032 (15) | 0.0618 (10) | |
H4A | 0.0062 | 0.3637 | −0.0658 | 0.074* | |
C5 | 0.2130 (4) | 0.3003 (5) | −0.04933 (13) | 0.0548 (9) | |
H5A | 0.1983 | 0.2811 | −0.0143 | 0.066* | |
C6 | 0.3507 (3) | 0.2803 (4) | −0.06939 (12) | 0.0431 (8) | |
C7 | 0.4769 (3) | 0.2416 (4) | −0.03535 (12) | 0.0426 (8) | |
C8 | 0.4740 (4) | 0.2821 (4) | 0.01696 (13) | 0.0502 (9) | |
H8A | 0.3892 | 0.3289 | 0.0310 | 0.060* | |
C9 | 0.5914 (4) | 0.2560 (5) | 0.04891 (13) | 0.0512 (9) | |
H9A | 0.5839 | 0.2819 | 0.0839 | 0.061* | |
C10 | 0.7212 (3) | 0.1910 (4) | 0.02908 (12) | 0.0441 (8) | |
C11 | 0.7267 (4) | 0.1514 (5) | −0.02322 (13) | 0.0526 (9) | |
H11A | 0.8127 | 0.1087 | −0.0374 | 0.063* | |
C12 | 0.6070 (4) | 0.1741 (5) | −0.05464 (13) | 0.0515 (9) | |
H12A | 0.6133 | 0.1438 | −0.0894 | 0.062* | |
C13 | 0.8543 (4) | 0.1702 (5) | 0.06013 (13) | 0.0487 (9) | |
C14 | 0.9399 (4) | 0.1239 (5) | 0.15061 (12) | 0.0496 (9) | |
C15 | 1.2018 (3) | 0.1052 (5) | 0.16435 (12) | 0.0464 (9) | |
C16 | 1.3065 (4) | 0.2418 (5) | 0.16584 (12) | 0.0517 (9) | |
C17 | 1.4339 (4) | 0.2124 (7) | 0.19269 (15) | 0.0722 (12) | |
H17A | 1.5049 | 0.3036 | 0.1934 | 0.087* | |
C18 | 1.4555 (4) | 0.0495 (8) | 0.21814 (15) | 0.0808 (14) | |
H18A | 1.5412 | 0.0305 | 0.2364 | 0.097* | |
C19 | 1.3519 (5) | −0.0868 (7) | 0.21709 (14) | 0.0812 (13) | |
H19A | 1.3671 | −0.1973 | 0.2347 | 0.097* | |
C20 | 1.2259 (4) | −0.0589 (6) | 0.18997 (13) | 0.0645 (11) | |
H20A | 1.1562 | −0.1516 | 0.1889 | 0.077* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0681 (7) | 0.0663 (7) | 0.1108 (9) | −0.0126 (6) | 0.0092 (6) | 0.0044 (7) |
S1 | 0.0552 (6) | 0.1315 (11) | 0.0477 (6) | −0.0086 (6) | 0.0052 (5) | −0.0061 (6) |
O1 | 0.0459 (15) | 0.096 (2) | 0.0570 (16) | −0.0027 (14) | 0.0110 (12) | 0.0065 (14) |
N1 | 0.0387 (18) | 0.067 (2) | 0.0453 (19) | −0.0106 (16) | 0.0027 (15) | −0.0040 (15) |
N2 | 0.0409 (18) | 0.071 (2) | 0.0447 (19) | −0.0087 (15) | 0.0037 (15) | 0.0036 (17) |
C1 | 0.050 (2) | 0.072 (3) | 0.048 (2) | −0.0094 (19) | 0.0071 (18) | −0.002 (2) |
C2 | 0.067 (3) | 0.092 (3) | 0.050 (2) | −0.010 (2) | −0.005 (2) | 0.006 (2) |
C3 | 0.052 (2) | 0.071 (3) | 0.069 (3) | −0.004 (2) | −0.008 (2) | 0.007 (2) |
C4 | 0.049 (2) | 0.067 (3) | 0.069 (3) | 0.0027 (19) | 0.007 (2) | 0.001 (2) |
C5 | 0.057 (2) | 0.053 (2) | 0.055 (2) | −0.0055 (18) | 0.010 (2) | 0.0032 (19) |
C6 | 0.048 (2) | 0.034 (2) | 0.048 (2) | −0.0089 (16) | 0.0040 (17) | 0.0003 (16) |
C7 | 0.049 (2) | 0.035 (2) | 0.043 (2) | −0.0113 (16) | 0.0084 (17) | 0.0013 (16) |
C8 | 0.046 (2) | 0.052 (2) | 0.052 (2) | −0.0012 (17) | 0.0104 (18) | −0.0009 (19) |
C9 | 0.055 (2) | 0.055 (2) | 0.043 (2) | −0.0039 (18) | 0.0033 (18) | −0.0032 (18) |
C10 | 0.049 (2) | 0.039 (2) | 0.043 (2) | −0.0098 (16) | 0.0041 (17) | −0.0018 (17) |
C11 | 0.049 (2) | 0.055 (2) | 0.054 (2) | −0.0022 (18) | 0.0115 (18) | −0.0031 (19) |
C12 | 0.053 (2) | 0.054 (2) | 0.048 (2) | −0.0052 (18) | 0.0076 (18) | −0.0029 (18) |
C13 | 0.052 (2) | 0.046 (2) | 0.048 (2) | −0.0071 (17) | 0.0042 (19) | −0.0005 (17) |
C14 | 0.049 (2) | 0.051 (2) | 0.049 (2) | −0.0133 (17) | 0.0039 (18) | −0.0087 (18) |
C15 | 0.040 (2) | 0.055 (3) | 0.044 (2) | 0.0010 (18) | 0.0050 (16) | −0.0039 (19) |
C16 | 0.050 (2) | 0.056 (2) | 0.049 (2) | −0.0038 (19) | 0.0036 (18) | −0.0089 (19) |
C17 | 0.048 (3) | 0.106 (4) | 0.063 (3) | −0.013 (2) | 0.004 (2) | −0.013 (3) |
C18 | 0.050 (3) | 0.137 (5) | 0.056 (3) | 0.013 (3) | −0.002 (2) | 0.004 (3) |
C19 | 0.069 (3) | 0.112 (4) | 0.062 (3) | 0.016 (3) | 0.009 (2) | 0.025 (3) |
C20 | 0.063 (3) | 0.071 (3) | 0.060 (2) | 0.001 (2) | 0.009 (2) | 0.011 (2) |
Cl1—C16 | 1.729 (4) | C7—C8 | 1.388 (4) |
S1—C14 | 1.647 (3) | C7—C12 | 1.393 (4) |
O1—C13 | 1.222 (3) | C8—C9 | 1.375 (4) |
N1—C13 | 1.365 (4) | C8—H8A | 0.9300 |
N1—C14 | 1.393 (4) | C9—C10 | 1.390 (4) |
N1—H1A | 0.855 (10) | C9—H9A | 0.9300 |
N2—C14 | 1.332 (4) | C10—C11 | 1.387 (4) |
N2—C15 | 1.413 (4) | C10—C13 | 1.475 (4) |
N2—H2A | 0.865 (10) | C11—C12 | 1.381 (4) |
C1—C2 | 1.373 (5) | C11—H11A | 0.9300 |
C1—C6 | 1.380 (4) | C12—H12A | 0.9300 |
C1—H1B | 0.9300 | C15—C20 | 1.378 (5) |
C2—C3 | 1.360 (5) | C15—C16 | 1.383 (4) |
C2—H2B | 0.9300 | C16—C17 | 1.382 (5) |
C3—C4 | 1.361 (5) | C17—C18 | 1.364 (5) |
C3—H3A | 0.9300 | C17—H17A | 0.9300 |
C4—C5 | 1.379 (4) | C18—C19 | 1.374 (6) |
C4—H4A | 0.9300 | C18—H18A | 0.9300 |
C5—C6 | 1.386 (4) | C19—C20 | 1.373 (5) |
C5—H5A | 0.9300 | C19—H19A | 0.9300 |
C6—C7 | 1.486 (4) | C20—H20A | 0.9300 |
C13—N1—C14 | 129.6 (3) | C11—C10—C9 | 117.9 (3) |
C13—N1—H1A | 115 (2) | C11—C10—C13 | 118.5 (3) |
C14—N1—H1A | 116 (2) | C9—C10—C13 | 123.5 (3) |
C14—N2—C15 | 126.4 (3) | C12—C11—C10 | 121.3 (3) |
C14—N2—H2A | 114 (2) | C12—C11—H11A | 119.4 |
C15—N2—H2A | 119 (2) | C10—C11—H11A | 119.4 |
C2—C1—C6 | 121.4 (3) | C11—C12—C7 | 121.4 (3) |
C2—C1—H1B | 119.3 | C11—C12—H12A | 119.3 |
C6—C1—H1B | 119.3 | C7—C12—H12A | 119.3 |
C3—C2—C1 | 120.8 (4) | O1—C13—N1 | 121.9 (3) |
C3—C2—H2B | 119.6 | O1—C13—C10 | 121.6 (3) |
C1—C2—H2B | 119.6 | N1—C13—C10 | 116.4 (3) |
C2—C3—C4 | 119.0 (3) | N2—C14—N1 | 114.2 (3) |
C2—C3—H3A | 120.5 | N2—C14—S1 | 126.5 (3) |
C4—C3—H3A | 120.5 | N1—C14—S1 | 119.3 (2) |
C3—C4—C5 | 120.5 (3) | C20—C15—C16 | 119.4 (3) |
C3—C4—H4A | 119.7 | C20—C15—N2 | 120.8 (3) |
C5—C4—H4A | 119.7 | C16—C15—N2 | 119.7 (3) |
C4—C5—C6 | 121.3 (3) | C17—C16—C15 | 119.9 (4) |
C4—C5—H5A | 119.4 | C17—C16—Cl1 | 120.4 (3) |
C6—C5—H5A | 119.4 | C15—C16—Cl1 | 119.7 (3) |
C1—C6—C5 | 116.8 (3) | C18—C17—C16 | 119.9 (4) |
C1—C6—C7 | 122.0 (3) | C18—C17—H17A | 120.0 |
C5—C6—C7 | 121.1 (3) | C16—C17—H17A | 120.0 |
C8—C7—C12 | 116.5 (3) | C17—C18—C19 | 120.6 (4) |
C8—C7—C6 | 121.5 (3) | C17—C18—H18A | 119.7 |
C12—C7—C6 | 121.9 (3) | C19—C18—H18A | 119.7 |
C9—C8—C7 | 122.7 (3) | C20—C19—C18 | 119.7 (4) |
C9—C8—H8A | 118.6 | C20—C19—H19A | 120.2 |
C7—C8—H8A | 118.6 | C18—C19—H19A | 120.2 |
C8—C9—C10 | 120.2 (3) | C19—C20—C15 | 120.5 (4) |
C8—C9—H9A | 119.9 | C19—C20—H20A | 119.7 |
C10—C9—H9A | 119.9 | C15—C20—H20A | 119.7 |
C6—C1—C2—C3 | −1.4 (6) | C14—N1—C13—C10 | −178.2 (3) |
C1—C2—C3—C4 | 0.4 (6) | C11—C10—C13—O1 | 24.0 (5) |
C2—C3—C4—C5 | −0.5 (6) | C9—C10—C13—O1 | −153.1 (3) |
C3—C4—C5—C6 | 1.6 (5) | C11—C10—C13—N1 | −156.7 (3) |
C2—C1—C6—C5 | 2.4 (5) | C9—C10—C13—N1 | 26.2 (5) |
C2—C1—C6—C7 | −175.8 (3) | C15—N2—C14—N1 | −176.2 (3) |
C4—C5—C6—C1 | −2.5 (5) | C15—N2—C14—S1 | 5.1 (5) |
C4—C5—C6—C7 | 175.7 (3) | C13—N1—C14—N2 | −0.9 (5) |
C1—C6—C7—C8 | 156.9 (3) | C13—N1—C14—S1 | 177.9 (3) |
C5—C6—C7—C8 | −21.2 (5) | C14—N2—C15—C20 | 60.3 (5) |
C1—C6—C7—C12 | −18.9 (5) | C14—N2—C15—C16 | −123.6 (4) |
C5—C6—C7—C12 | 163.0 (3) | C20—C15—C16—C17 | 0.3 (5) |
C12—C7—C8—C9 | −0.8 (5) | N2—C15—C16—C17 | −175.8 (3) |
C6—C7—C8—C9 | −176.8 (3) | C20—C15—C16—Cl1 | 179.8 (2) |
C7—C8—C9—C10 | 1.7 (5) | N2—C15—C16—Cl1 | 3.7 (4) |
C8—C9—C10—C11 | −1.0 (5) | C15—C16—C17—C18 | −0.7 (5) |
C8—C9—C10—C13 | 176.1 (3) | Cl1—C16—C17—C18 | 179.8 (3) |
C9—C10—C11—C12 | −0.5 (5) | C16—C17—C18—C19 | 0.4 (6) |
C13—C10—C11—C12 | −177.8 (3) | C17—C18—C19—C20 | 0.3 (6) |
C10—C11—C12—C7 | 1.4 (5) | C18—C19—C20—C15 | −0.8 (6) |
C8—C7—C12—C11 | −0.7 (5) | C16—C15—C20—C19 | 0.5 (5) |
C6—C7—C12—C11 | 175.3 (3) | N2—C15—C20—C19 | 176.5 (3) |
C14—N1—C13—O1 | 1.1 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O1 | 0.86 (1) | 1.88 (2) | 2.619 (4) | 142 (3) |
Experimental details
Crystal data | |
Chemical formula | C20H15ClN2OS |
Mr | 366.85 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 298 |
a, b, c (Å) | 9.2448 (14), 7.2284 (11), 25.934 (4) |
β (°) | 90.295 (3) |
V (Å3) | 1733.0 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.35 |
Crystal size (mm) | 0.50 × 0.30 × 0.07 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2000) |
Tmin, Tmax | 0.844, 0.975 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8945, 3219, 1742 |
Rint | 0.064 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.063, 0.131, 1.02 |
No. of reflections | 3219 |
No. of parameters | 234 |
No. of restraints | 2 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.17, −0.17 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SAINT, SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O1 | 0.863 (12) | 1.882 (18) | 2.619 (4) | 142 (3) |
Many aroylthiourea compounds reported so far are based on a benzene group. The title compound, (I), is also an aroylthiourea derivative but having a biphenyl group (Fig.1). The molecule maintains the trans-cis configuration with respect to the position of the biphenylcarbonyl and chlorobenzene groups about the thiono sulfur atom across their C14—N1 and C14—N2 bonds, respectively. The biphenyl fragment is not planar with C1—C6—C7—C12 and C5—C6—C7—C8 torsion angles of -18.9 (5) and -21.2 (5)° respectively. The bond lengths and angles are in normal ranges (Allen et al., 1987) and close to those observed in (II) (Yusof & Yamin, 2004) and (III) (Shoukat et al., 2007). The benzene C7—C12, the carbonyl-thiourea C13/O1/N1/C14/S1/N2 and the chlorobenzene Cl1/C15—C20 fragments are each planar with maximum deviation of 0.026 (3)Å for N1 atom from the least squares plane of the carbonyl-thiourea moiety. The central carbonyl-thiourea moiety makes dihedral angles with the C7—C12 benzene ring and chlorobenzene fragment of 24.39 (13) and 61.63 (10)°, respectively. There is an N2—H2A···O1 intramolecular hydrogen bond (D—H= 0.863 (12), H···A= 1.882 (18) D···A= 2.619 (4)Å and D—H···A =142 (3)°) formimg a pseudo six-membered ring [C13—N1—C14—N2—H2A···O1]. The crystal packing is stabilized by weak van der Waals and π···π interactions, between the benzene (C7—C12)i rings ((i): 1 - x, -y, -z) with the distance between the centroids of 3.629 (2) Å.