1-(3-Chloro­benzo­yl)-3-phenyl­thio­urea

Khawar Rauf, M.; Badshah, A.; Bolte, M.

doi:10.1107/S1600536806012773

1-(3-Chlorobenzoyl)-3-phenylthiourea

The phenyl and benzoyl groups in the title compound, C₁₄H₁₁ClN₂OS, are cis and trans, respectively, with respect to the C=S bond. The crystal packing is characterized by N—H

O and N—H

S hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806012773/fl2016sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806012773/fl2016Isup2.hkl Contains datablock I

CCDC reference: 608329

checkCIF report

Key indicators

Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.002 Å
R factor = 0.037
wR factor = 0.102
Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    S1     -   C2      ..       5.99 su

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PLATON.

1-(3-Chlorobenzoyl)-3-phenylthiourea top

Crystal data top

C₁₄H₁₁ClN₂OS	F(000) = 300
M_r = 290.76	D_x = 1.446 Mg m⁻³
Triclinic, P1	Melting point: 410 K
a = 7.6340 (12) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.8940 (14) Å	Cell parameters from 5339 reflections
c = 11.0219 (18) Å	θ = 3.9–25.6°
α = 83.129 (13)°	µ = 0.43 mm⁻¹
β = 70.328 (12)°	T = 173 K
γ = 71.382 (12)°	Block, colourless
V = 667.74 (18) Å³	0.47 × 0.44 × 0.42 mm
Z = 2

Data collection top

Stoe IPDS-II two-circle diffractometer	2471 independent reflections
Radiation source: fine-focus sealed tube	2242 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
ω scans	θ_max = 25.6°, θ_min = 3.9°
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)	h = −9→9
T_min = 0.822, T_max = 0.839	k = −10→9
5414 measured reflections	l = −13→12

Refinement top

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-atom parameters constrained
wR(F²) = 0.102	w = 1/[σ²(F_o²) + (0.0614P)² + 0.294P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
2471 reflections	Δρ_max = 0.31 e Å⁻³
173 parameters	Δρ_min = −0.40 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.081 (7)

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.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.74465 (7)	1.33073 (5)	0.94282 (4)	0.02720 (18)
S1	0.87654 (7)	0.91439 (5)	0.39177 (4)	0.02330 (17)
C1	0.7434 (2)	0.8092 (2)	0.76852 (16)	0.0165 (4)
O1	0.6825 (2)	0.69257 (15)	0.79108 (12)	0.0236 (3)
N1	0.8059 (2)	0.86939 (17)	0.64438 (14)	0.0181 (3)
H1	0.8615	0.9445	0.6356	0.022*
C2	0.7906 (2)	0.8245 (2)	0.53194 (16)	0.0168 (4)
N2	0.7031 (2)	0.71214 (18)	0.54496 (14)	0.0210 (3)
H2	0.6646	0.6704	0.6222	0.025*
C11	0.7531 (2)	0.8957 (2)	0.87342 (16)	0.0156 (4)
C12	0.7468 (2)	1.0554 (2)	0.86095 (16)	0.0163 (4)
H12	0.7402	1.1119	0.7830	0.020*
C13	0.7504 (2)	1.1315 (2)	0.96279 (16)	0.0179 (4)
C14	0.7579 (2)	1.0513 (2)	1.07833 (17)	0.0209 (4)
H14	0.7606	1.1039	1.1475	0.025*
C15	0.7614 (3)	0.8926 (2)	1.09105 (17)	0.0222 (4)
H15	0.7663	0.8370	1.1696	0.027*
C16	0.7577 (2)	0.8142 (2)	0.99013 (16)	0.0191 (4)
H16	0.7584	0.7065	1.0002	0.023*
C21	0.6678 (3)	0.6550 (2)	0.44133 (16)	0.0174 (4)
C22	0.8217 (3)	0.5556 (2)	0.34859 (18)	0.0225 (4)
H22	0.9517	0.5309	0.3498	0.027*
C23	0.7819 (3)	0.4934 (2)	0.25427 (18)	0.0259 (4)
H23	0.8856	0.4264	0.1903	0.031*
C24	0.5910 (3)	0.5285 (2)	0.25301 (17)	0.0233 (4)
H24	0.5647	0.4851	0.1887	0.028*
C25	0.4395 (3)	0.6272 (2)	0.34593 (18)	0.0218 (4)
H25	0.3093	0.6505	0.3454	0.026*
C26	0.4772 (3)	0.6924 (2)	0.44040 (16)	0.0198 (4)
H26	0.3737	0.7615	0.5031	0.024*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0376 (3)	0.0210 (3)	0.0261 (3)	−0.00755 (19)	−0.0129 (2)	−0.00693 (18)
S1	0.0379 (3)	0.0302 (3)	0.0102 (2)	−0.0225 (2)	−0.00708 (19)	0.00142 (18)
C1	0.0184 (8)	0.0188 (8)	0.0127 (8)	−0.0058 (6)	−0.0052 (6)	−0.0002 (6)
O1	0.0367 (7)	0.0245 (7)	0.0154 (6)	−0.0181 (6)	−0.0075 (5)	0.0016 (5)
N1	0.0278 (8)	0.0216 (7)	0.0107 (7)	−0.0156 (6)	−0.0058 (6)	0.0000 (5)
C2	0.0209 (8)	0.0179 (8)	0.0131 (8)	−0.0063 (7)	−0.0056 (6)	−0.0032 (6)
N2	0.0338 (8)	0.0239 (8)	0.0117 (7)	−0.0182 (6)	−0.0068 (6)	0.0009 (6)
C11	0.0149 (8)	0.0220 (8)	0.0108 (8)	−0.0059 (6)	−0.0040 (6)	−0.0022 (6)
C12	0.0164 (8)	0.0211 (8)	0.0108 (8)	−0.0045 (6)	−0.0042 (6)	−0.0015 (6)
C13	0.0156 (8)	0.0210 (9)	0.0169 (8)	−0.0041 (6)	−0.0049 (6)	−0.0045 (7)
C14	0.0175 (8)	0.0328 (10)	0.0144 (8)	−0.0064 (7)	−0.0064 (7)	−0.0066 (7)
C15	0.0228 (9)	0.0329 (10)	0.0117 (8)	−0.0082 (7)	−0.0077 (7)	0.0025 (7)
C16	0.0210 (9)	0.0231 (9)	0.0140 (8)	−0.0083 (7)	−0.0056 (7)	0.0024 (7)
C21	0.0285 (9)	0.0162 (8)	0.0122 (8)	−0.0126 (7)	−0.0073 (7)	0.0018 (6)
C22	0.0233 (9)	0.0242 (9)	0.0222 (9)	−0.0085 (7)	−0.0080 (7)	−0.0029 (7)
C23	0.0323 (10)	0.0255 (10)	0.0180 (9)	−0.0080 (8)	−0.0041 (8)	−0.0062 (7)
C24	0.0396 (11)	0.0236 (9)	0.0163 (9)	−0.0170 (8)	−0.0141 (8)	0.0011 (7)
C25	0.0272 (9)	0.0217 (9)	0.0228 (9)	−0.0121 (7)	−0.0141 (8)	0.0084 (7)
C26	0.0261 (9)	0.0158 (8)	0.0163 (8)	−0.0064 (7)	−0.0057 (7)	0.0018 (7)

Geometric parameters (Å, º) top

Cl1—C13	1.7476 (19)	C14—H14	0.9500
S1—C2	1.6772 (18)	C15—C16	1.393 (2)
C1—O1	1.233 (2)	C15—H15	0.9500
C1—N1	1.391 (2)	C16—H16	0.9500
C1—C11	1.497 (2)	C21—C26	1.389 (3)
N1—C2	1.398 (2)	C21—C22	1.397 (2)
N1—H1	0.8800	C22—C23	1.392 (3)
C2—N2	1.339 (2)	C22—H22	0.9500
N2—C21	1.438 (2)	C23—C24	1.394 (3)
N2—H2	0.8800	C23—H23	0.9500
C11—C12	1.398 (2)	C24—C25	1.388 (3)
C11—C16	1.404 (2)	C24—H24	0.9500
C12—C13	1.390 (2)	C25—C26	1.399 (3)
C12—H12	0.9500	C25—H25	0.9500
C13—C14	1.393 (3)	C26—H26	0.9500
C14—C15	1.394 (3)

O1—C1—N1	122.24 (15)	C16—C15—C14	120.90 (16)
O1—C1—C11	122.01 (15)	C16—C15—H15	119.5
N1—C1—C11	115.75 (15)	C14—C15—H15	119.5
C1—N1—C2	127.60 (15)	C15—C16—C11	119.55 (16)
C1—N1—H1	116.2	C15—C16—H16	120.2
C2—N1—H1	116.2	C11—C16—H16	120.2
N2—C2—N1	116.51 (15)	C26—C21—C22	121.07 (16)
N2—C2—S1	124.15 (13)	C26—C21—N2	118.65 (15)
N1—C2—S1	119.33 (13)	C22—C21—N2	120.15 (16)
C2—N2—C21	124.46 (15)	C23—C22—C21	119.03 (17)
C2—N2—H2	117.8	C23—C22—H22	120.5
C21—N2—H2	117.8	C21—C22—H22	120.5
C12—C11—C16	119.68 (15)	C22—C23—C24	120.51 (17)
C12—C11—C1	122.18 (15)	C22—C23—H23	119.7
C16—C11—C1	118.04 (15)	C24—C23—H23	119.7
C13—C12—C11	119.89 (15)	C25—C24—C23	119.83 (17)
C13—C12—H12	120.1	C25—C24—H24	120.1
C11—C12—H12	120.1	C23—C24—H24	120.1
C12—C13—C14	120.92 (17)	C24—C25—C26	120.42 (17)
C12—C13—Cl1	118.47 (13)	C24—C25—H25	119.8
C14—C13—Cl1	120.61 (14)	C26—C25—H25	119.8
C13—C14—C15	119.04 (16)	C21—C26—C25	119.13 (16)
C13—C14—H14	120.5	C21—C26—H26	120.4
C15—C14—H14	120.5	C25—C26—H26	120.4

O1—C1—N1—C2	7.9 (3)	Cl1—C13—C14—C15	179.70 (13)
C11—C1—N1—C2	−171.62 (15)	C13—C14—C15—C16	0.1 (3)
C1—N1—C2—N2	1.1 (3)	C14—C15—C16—C11	0.8 (3)
C1—N1—C2—S1	179.90 (13)	C12—C11—C16—C15	−1.7 (2)
N1—C2—N2—C21	177.63 (15)	C1—C11—C16—C15	−178.23 (15)
S1—C2—N2—C21	−1.1 (3)	C2—N2—C21—C26	−110.3 (2)
O1—C1—C11—C12	−154.50 (17)	C2—N2—C21—C22	73.8 (2)
N1—C1—C11—C12	25.1 (2)	C26—C21—C22—C23	−0.2 (3)
O1—C1—C11—C16	21.9 (2)	N2—C21—C22—C23	175.71 (16)
N1—C1—C11—C16	−158.53 (15)	C21—C22—C23—C24	−0.5 (3)
C16—C11—C12—C13	1.7 (2)	C22—C23—C24—C25	0.4 (3)
C1—C11—C12—C13	178.04 (15)	C23—C24—C25—C26	0.4 (3)
C11—C12—C13—C14	−0.8 (2)	C22—C21—C26—C25	1.0 (3)
C11—C12—C13—Cl1	179.41 (12)	N2—C21—C26—C25	−174.96 (15)
C12—C13—C14—C15	−0.1 (2)	C24—C25—C26—C21	−1.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S1ⁱ	0.88	2.60	3.4465 (16)	161
N2—H2···O1	0.88	1.95	2.6516 (19)	136

Symmetry code: (i) −x+2, −y+2, −z+1.

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1-(3-Chloro­benzo­yl)-3-phenyl­thio­urea

Supporting information

Key indicators

checkCIF/PLATON results

1-(3-Chlorobenzoyl)-3-phenylthiourea