1-Benzoyl-3-(4-chloro­phen­yl)thio­urea

Khawar Rauf, M.; Badshah, A.; Flörke, U.; Saeed, A.

doi:10.1107/S160053680600910X

1-Benzoyl-3-(4-chlorophenyl)thiourea

M. Khawar Rauf, A. Badshah, U. Flörke and A. Saeed

In the crystal structure of the title compound, C₁₄H₁₁ClN₂OS, the dihedral angle between the two aromatic ring planes is 43.93 (6)°. The crystal packing shows dimers formed by intermolecular N—H

S hydrogen bonds which are stacked along [100].

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680600910X/bt2023sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680600910X/bt2023Isup2.hkl Contains datablock I

CCDC reference: 604982

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Key indicators

Single-crystal X-ray study
T = 120 K
Mean (C-C) = 0.003 Å
R factor = 0.044
wR factor = 0.111
Data-to-parameter ratio = 16.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT432_ALERT_2_C Short Inter X...Y Contact  S1     ..  C14     ..       3.21 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 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
   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: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2002); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

1-benzoyl-3-(4-chlorophenyl)thiourea top

Crystal data top

C₁₄H₁₁ClN₂OS	Z = 2
M_r = 290.76	F(000) = 300
Triclinic, P1	D_x = 1.484 Mg m⁻³
a = 3.9530 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.2293 (14) Å	Cell parameters from 1779 reflections
c = 14.8754 (17) Å	θ = 2.8–26.2°
α = 65.832 (2)°	µ = 0.45 mm⁻¹
β = 89.487 (2)°	T = 120 K
γ = 82.995 (3)°	Needle, colorless
V = 650.52 (13) Å³	0.43 × 0.19 × 0.06 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2884 independent reflections
Radiation source: sealed tube	2424 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
φ and ω scans	θ_max = 27.3°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −5→5
T_min = 0.832, T_max = 0.974	k = −15→13
5434 measured reflections	l = −19→18

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)] = 0.044	Hydrogen site location: difference Fourier map
wR(F²) = 0.111	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0585P)² + 0.0457P] where P = (F_o² + 2F_c²)/3
2884 reflections	(Δ/σ)_max < 0.001
172 parameters	Δρ_max = 0.49 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

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	−0.32523 (15)	−0.15813 (5)	0.46103 (4)	0.03529 (18)
S1	0.28439 (13)	0.38422 (4)	0.12246 (3)	0.02085 (15)
O1	0.3094 (4)	0.19386 (13)	−0.08349 (10)	0.0284 (4)
N1	0.1260 (4)	0.19714 (14)	0.08655 (11)	0.0196 (4)
H1A	0.1195	0.1700	0.0402	0.023*
N2	0.3399 (4)	0.35176 (14)	−0.04063 (11)	0.0190 (4)
H2B	0.3928	0.4259	−0.0634	0.023*
C1	0.0119 (5)	0.11961 (17)	0.17882 (13)	0.0186 (4)
C2	0.0109 (5)	0.13927 (18)	0.26408 (14)	0.0237 (4)
H2A	0.0832	0.2109	0.2634	0.028*
C3	−0.0965 (6)	0.05372 (19)	0.35063 (14)	0.0263 (5)
H3A	−0.0981	0.0666	0.4095	0.032*
C4	−0.2010 (5)	−0.05007 (18)	0.35090 (15)	0.0240 (5)
C5	−0.2081 (5)	−0.06938 (18)	0.26676 (15)	0.0244 (5)
H5A	−0.2866	−0.1402	0.2676	0.029*
C6	−0.0996 (5)	0.01544 (18)	0.18009 (15)	0.0226 (4)
H6A	−0.1015	0.0023	0.1214	0.027*
C7	0.2417 (5)	0.30431 (17)	0.05759 (13)	0.0169 (4)
C8	0.3647 (5)	0.29837 (18)	−0.10588 (13)	0.0200 (4)
C9	0.4671 (5)	0.37530 (17)	−0.20650 (13)	0.0184 (4)
C10	0.6567 (5)	0.31817 (18)	−0.25793 (14)	0.0222 (4)
H10A	0.7216	0.2332	−0.2280	0.027*
C11	0.7508 (5)	0.3850 (2)	−0.35252 (15)	0.0253 (5)
H11A	0.8825	0.3463	−0.3875	0.030*
C12	0.6517 (5)	0.5089 (2)	−0.39617 (14)	0.0260 (5)
H12A	0.7169	0.5550	−0.4611	0.031*
C13	0.4592 (5)	0.56560 (19)	−0.34596 (14)	0.0240 (5)
H13A	0.3899	0.6503	−0.3767	0.029*
C14	0.3669 (5)	0.49903 (18)	−0.25064 (14)	0.0211 (4)
H14A	0.2356	0.5380	−0.2158	0.025*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0427 (4)	0.0239 (3)	0.0278 (3)	−0.0119 (2)	0.0121 (2)	0.0027 (2)
S1	0.0289 (3)	0.0168 (3)	0.0174 (2)	−0.0086 (2)	0.00585 (19)	−0.00612 (19)
O1	0.0478 (10)	0.0171 (7)	0.0222 (7)	−0.0115 (7)	0.0084 (6)	−0.0079 (6)
N1	0.0278 (9)	0.0151 (8)	0.0154 (8)	−0.0066 (7)	0.0034 (7)	−0.0050 (6)
N2	0.0276 (9)	0.0123 (8)	0.0150 (8)	−0.0056 (7)	0.0037 (6)	−0.0029 (6)
C1	0.0195 (10)	0.0137 (9)	0.0167 (9)	−0.0011 (8)	0.0014 (7)	−0.0007 (7)
C2	0.0325 (12)	0.0159 (10)	0.0202 (10)	−0.0066 (9)	0.0031 (8)	−0.0039 (8)
C3	0.0356 (12)	0.0225 (11)	0.0165 (9)	−0.0055 (9)	0.0038 (8)	−0.0033 (8)
C4	0.0239 (11)	0.0162 (10)	0.0234 (10)	−0.0041 (8)	0.0064 (8)	0.0007 (8)
C5	0.0245 (11)	0.0145 (10)	0.0300 (11)	−0.0068 (8)	0.0040 (8)	−0.0039 (8)
C6	0.0249 (11)	0.0192 (10)	0.0222 (10)	−0.0046 (8)	0.0025 (8)	−0.0066 (8)
C7	0.0161 (9)	0.0138 (9)	0.0161 (9)	−0.0005 (7)	−0.0002 (7)	−0.0017 (7)
C8	0.0215 (10)	0.0187 (10)	0.0180 (9)	−0.0026 (8)	0.0012 (7)	−0.0058 (8)
C9	0.0221 (10)	0.0192 (10)	0.0140 (9)	−0.0070 (8)	0.0011 (7)	−0.0058 (7)
C10	0.0260 (11)	0.0207 (10)	0.0213 (10)	−0.0050 (8)	0.0011 (8)	−0.0095 (8)
C11	0.0248 (11)	0.0333 (12)	0.0221 (10)	−0.0084 (9)	0.0057 (8)	−0.0147 (9)
C12	0.0299 (12)	0.0324 (12)	0.0146 (9)	−0.0141 (9)	0.0047 (8)	−0.0060 (8)
C13	0.0290 (12)	0.0197 (10)	0.0189 (9)	−0.0067 (9)	−0.0012 (8)	−0.0026 (8)
C14	0.0234 (11)	0.0218 (10)	0.0186 (9)	−0.0052 (8)	0.0017 (8)	−0.0081 (8)

Geometric parameters (Å, º) top

Cl1—C4	1.7443 (19)	C5—C6	1.388 (3)
S1—C7	1.652 (2)	C5—H5A	0.9500
O1—C8	1.229 (2)	C6—H6A	0.9500
N1—C7	1.339 (2)	C8—C9	1.490 (2)
N1—C1	1.419 (2)	C9—C14	1.387 (3)
N1—H1A	0.8800	C9—C10	1.391 (3)
N2—C8	1.371 (2)	C10—C11	1.382 (3)
N2—C7	1.404 (2)	C10—H10A	0.9500
N2—H2B	0.8800	C11—C12	1.387 (3)
C1—C2	1.384 (3)	C11—H11A	0.9500
C1—C6	1.391 (3)	C12—C13	1.380 (3)
C2—C3	1.389 (3)	C12—H12A	0.9500
C2—H2A	0.9500	C13—C14	1.387 (3)
C3—C4	1.380 (3)	C13—H13A	0.9500
C3—H3A	0.9500	C14—H14A	0.9500
C4—C5	1.367 (3)

C7—N1—C1	131.30 (17)	N1—C7—N2	114.11 (17)
C7—N1—H1A	114.3	N1—C7—S1	128.34 (14)
C1—N1—H1A	114.3	N2—C7—S1	117.55 (14)
C8—N2—C7	128.88 (16)	O1—C8—N2	122.81 (17)
C8—N2—H2B	115.6	O1—C8—C9	121.70 (17)
C7—N2—H2B	115.6	N2—C8—C9	115.48 (17)
C2—C1—C6	119.82 (18)	C14—C9—C10	120.11 (17)
C2—C1—N1	125.47 (18)	C14—C9—C8	122.11 (17)
C6—C1—N1	114.70 (17)	C10—C9—C8	117.71 (17)
C1—C2—C3	119.6 (2)	C11—C10—C9	120.04 (19)
C1—C2—H2A	120.2	C11—C10—H10A	120.0
C3—C2—H2A	120.2	C9—C10—H10A	120.0
C4—C3—C2	119.75 (19)	C10—C11—C12	119.65 (19)
C4—C3—H3A	120.1	C10—C11—H11A	120.2
C2—C3—H3A	120.1	C12—C11—H11A	120.2
C5—C4—C3	121.21 (18)	C13—C12—C11	120.48 (18)
C5—C4—Cl1	119.73 (16)	C13—C12—H12A	119.8
C3—C4—Cl1	119.06 (16)	C11—C12—H12A	119.8
C4—C5—C6	119.34 (19)	C12—C13—C14	120.05 (19)
C4—C5—H5A	120.3	C12—C13—H13A	120.0
C6—C5—H5A	120.3	C14—C13—H13A	120.0
C5—C6—C1	120.23 (19)	C9—C14—C13	119.65 (18)
C5—C6—H6A	119.9	C9—C14—H14A	120.2
C1—C6—H6A	119.9	C13—C14—H14A	120.2

C7—N1—C1—C2	−2.9 (3)	C8—N2—C7—S1	172.27 (15)
C7—N1—C1—C6	178.36 (19)	C7—N2—C8—O1	−2.4 (3)
C6—C1—C2—C3	1.0 (3)	C7—N2—C8—C9	178.21 (17)
N1—C1—C2—C3	−177.68 (19)	O1—C8—C9—C14	146.0 (2)
C1—C2—C3—C4	0.0 (3)	N2—C8—C9—C14	−34.5 (3)
C2—C3—C4—C5	−1.4 (3)	O1—C8—C9—C10	−31.1 (3)
C2—C3—C4—Cl1	178.47 (16)	N2—C8—C9—C10	148.36 (19)
C3—C4—C5—C6	1.8 (3)	C14—C9—C10—C11	1.1 (3)
Cl1—C4—C5—C6	−178.16 (15)	C8—C9—C10—C11	178.33 (18)
C4—C5—C6—C1	−0.7 (3)	C9—C10—C11—C12	−0.7 (3)
C2—C1—C6—C5	−0.7 (3)	C10—C11—C12—C13	−0.2 (3)
N1—C1—C6—C5	178.12 (17)	C11—C12—C13—C14	0.8 (3)
C1—N1—C7—N2	178.35 (18)	C10—C9—C14—C13	−0.6 (3)
C1—N1—C7—S1	−1.1 (3)	C8—C9—C14—C13	−177.62 (18)
C8—N2—C7—N1	−7.2 (3)	C12—C13—C14—C9	−0.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.88	1.90	2.640 (2)	140
N2—H2B···S1ⁱ	0.88	2.61	3.4686 (17)	165

Symmetry code: (i) −x+1, −y+1, −z.

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1-Benzoyl-3-(4-chloro­phen­yl)thio­urea

Supporting information

Key indicators

checkCIF/PLATON results

1-Benzoyl-3-(4-chlorophenyl)thiourea