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

In the mol­ecule of the title compound, C₁₄H₁₁ClN₂OS, the dihedral angle between the two aromatic rings is 19.02 (9)°. In the crystal packing, the mol­ecules are linked by inter­molecular C—H...S and N—H...S hydrogen bonds into centro­symmetric dimers stacked along the [010] direction.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C)= 0.002 Å
• R factor = 0.040
• wR factor = 0.091
• Data-to-parameter ratio = 18.3

checkCIF/PLATON results

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Computing details

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-(3-chlorophenyl)thiourea

Crystal data

C14H11ClN2OS	F(000) = 600
Mr = 290.76	Dx = 1.486 Mg m^−3
Monoclinic, P21/n	Melting point: 393 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 11.2191 (9) Å	Cell parameters from 3339 reflections
b = 4.5955 (4) Å	θ = 2.3–28.1°
c = 25.631 (2) Å	µ = 0.45 mm^−1
β = 100.438 (2)°	T = 120 K
V = 1299.61 (19) Å^3	Prism, colourless
Z = 4	0.44 × 0.20 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer	3144 independent reflections
Radiation source: sealed tube	2510 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.058
φ and ω scans	θmax = 28.1°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −13→14
Tmin = 0.828, Tmax = 0.932	k = −5→6
12106 measured reflections	l = −33→33

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.040	Hydrogen site location: difference Fourier map
wR(F^2) = 0.091	H-atom parameters constrained
S = 0.96	w = 1/[σ^2(Fo^2) + (0.0488P)^2] where P = (Fo^2 + 2Fc^2)/3
3144 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.36 e Å^−3
0 restraints	Δρmin = −0.35 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.71466 (4)	1.44328 (10)	0.167424 (19)	0.03415 (14)
S1	0.90939 (4)	0.69429 (11)	0.053631 (15)	0.02801 (13)
O1	1.25206 (11)	0.4032 (3)	0.16313 (4)	0.0282 (3)
N1	1.05886 (12)	0.7242 (3)	0.14844 (5)	0.0198 (3)
H1A	1.1256	0.6501	0.1670	0.024*
N2	1.11053 (12)	0.4052 (3)	0.08727 (5)	0.0188 (3)
H2B	1.0901	0.3197	0.0562	0.023*
C1	1.00439 (14)	0.9389 (3)	0.17588 (6)	0.0194 (3)
C2	1.07128 (16)	1.0120 (4)	0.22559 (6)	0.0245 (4)
H2A	1.1468	0.9197	0.2381	0.029*
C3	1.02774 (17)	1.2182 (4)	0.25653 (6)	0.0286 (4)
H3A	1.0740	1.2677	0.2902	0.034*
C4	0.91801 (16)	1.3531 (4)	0.23922 (7)	0.0265 (4)
H4A	0.8876	1.4942	0.2605	0.032*
C5	0.85372 (14)	1.2771 (4)	0.19009 (6)	0.0229 (4)
C6	0.89429 (14)	1.0727 (3)	0.15774 (6)	0.0207 (3)
H6A	0.8478	1.0257	0.1240	0.025*
C7	1.02853 (14)	0.6120 (3)	0.09973 (6)	0.0184 (3)
C8	1.21898 (14)	0.3184 (4)	0.11730 (6)	0.0197 (3)
C9	1.29719 (14)	0.1236 (3)	0.09202 (6)	0.0188 (3)
C10	1.41988 (15)	0.1188 (4)	0.11472 (6)	0.0234 (4)
H10A	1.4484	0.2325	0.1454	0.028*
C11	1.49992 (16)	−0.0492 (4)	0.09302 (7)	0.0277 (4)
H11A	1.5836	−0.0497	0.1084	0.033*
C12	1.45831 (16)	−0.2175 (4)	0.04866 (7)	0.0306 (4)
H12A	1.5135	−0.3335	0.0336	0.037*
C13	1.33646 (16)	−0.2170 (4)	0.02616 (7)	0.0273 (4)
H13A	1.3082	−0.3330	−0.0042	0.033*
C14	1.25586 (15)	−0.0484 (4)	0.04775 (6)	0.0212 (3)
H14A	1.1722	−0.0499	0.0324	0.025*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0224 (2)	0.0312 (3)	0.0496 (3)	0.00389 (19)	0.00863 (19)	−0.0074 (2)
S1	0.0234 (2)	0.0413 (3)	0.0172 (2)	0.0115 (2)	−0.00195 (16)	−0.00391 (18)
O1	0.0255 (6)	0.0400 (8)	0.0169 (5)	0.0077 (5)	−0.0020 (5)	−0.0045 (5)
N1	0.0185 (7)	0.0240 (7)	0.0155 (6)	0.0025 (6)	−0.0005 (5)	−0.0011 (5)
N2	0.0188 (7)	0.0217 (7)	0.0147 (6)	0.0021 (5)	0.0000 (5)	−0.0030 (5)
C1	0.0214 (8)	0.0184 (8)	0.0195 (7)	−0.0022 (7)	0.0067 (6)	0.0009 (6)
C2	0.0286 (9)	0.0252 (9)	0.0192 (8)	0.0015 (7)	0.0025 (7)	0.0004 (7)
C3	0.0374 (11)	0.0291 (10)	0.0192 (8)	−0.0010 (8)	0.0052 (7)	−0.0045 (7)
C4	0.0326 (10)	0.0239 (9)	0.0261 (8)	−0.0009 (8)	0.0132 (7)	−0.0036 (7)
C5	0.0191 (8)	0.0215 (9)	0.0303 (9)	−0.0009 (7)	0.0102 (7)	0.0014 (7)
C6	0.0191 (8)	0.0222 (9)	0.0210 (8)	−0.0034 (7)	0.0043 (6)	−0.0010 (6)
C7	0.0174 (8)	0.0204 (8)	0.0177 (7)	−0.0009 (6)	0.0035 (6)	0.0015 (6)
C8	0.0186 (8)	0.0216 (8)	0.0185 (7)	−0.0016 (7)	0.0020 (6)	0.0035 (6)
C9	0.0195 (8)	0.0190 (8)	0.0177 (7)	0.0008 (6)	0.0029 (6)	0.0047 (6)
C10	0.0216 (9)	0.0247 (9)	0.0225 (8)	0.0009 (7)	0.0006 (7)	0.0000 (7)
C11	0.0196 (9)	0.0272 (9)	0.0354 (9)	0.0028 (7)	0.0024 (7)	0.0005 (8)
C12	0.0281 (10)	0.0267 (10)	0.0384 (10)	0.0061 (8)	0.0103 (8)	−0.0046 (8)
C13	0.0286 (10)	0.0259 (9)	0.0272 (9)	−0.0006 (8)	0.0042 (7)	−0.0060 (7)
C14	0.0205 (8)	0.0214 (9)	0.0210 (8)	−0.0003 (7)	0.0019 (6)	0.0038 (6)

Geometric parameters (Å, º)

Cl1—C5	1.7398 (17)	C4—H4A	0.9500
S1—C7	1.6594 (16)	C5—C6	1.383 (2)
O1—C8	1.2295 (18)	C6—H6A	0.9500
N1—C7	1.3367 (19)	C8—C9	1.482 (2)
N1—C1	1.413 (2)	C9—C14	1.392 (2)
N1—H1A	0.8800	C9—C10	1.394 (2)
N2—C8	1.376 (2)	C10—C11	1.376 (2)
N2—C7	1.399 (2)	C10—H10A	0.9500
N2—H2B	0.8800	C11—C12	1.385 (2)
C1—C6	1.383 (2)	C11—H11A	0.9500
C1—C2	1.398 (2)	C12—C13	1.384 (2)
C2—C3	1.380 (2)	C12—H12A	0.9500
C2—H2A	0.9500	C13—C14	1.380 (2)
C3—C4	1.378 (2)	C13—H13A	0.9500
C3—H3A	0.9500	C14—H14A	0.9500
C4—C5	1.378 (2)
C7—N1—C1	132.41 (14)	N1—C7—N2	114.12 (13)
C7—N1—H1A	113.8	N1—C7—S1	127.81 (13)
C1—N1—H1A	113.8	N2—C7—S1	118.06 (11)
C8—N2—C7	128.36 (13)	O1—C8—N2	121.73 (15)
C8—N2—H2B	115.8	O1—C8—C9	120.60 (14)
C7—N2—H2B	115.8	N2—C8—C9	117.65 (13)
C6—C1—C2	119.94 (15)	C14—C9—C10	119.30 (15)
C6—C1—N1	125.70 (14)	C14—C9—C8	124.28 (15)
C2—C1—N1	114.36 (14)	C10—C9—C8	116.41 (14)
C3—C2—C1	120.09 (16)	C11—C10—C9	120.49 (15)
C3—C2—H2A	120.0	C11—C10—H10A	119.8
C1—C2—H2A	120.0	C9—C10—H10A	119.8
C4—C3—C2	120.81 (16)	C10—C11—C12	119.87 (16)
C4—C3—H3A	119.6	C10—C11—H11A	120.1
C2—C3—H3A	119.6	C12—C11—H11A	120.1
C3—C4—C5	118.00 (15)	C13—C12—C11	120.11 (16)
C3—C4—H4A	121.0	C13—C12—H12A	119.9
C5—C4—H4A	121.0	C11—C12—H12A	119.9
C4—C5—C6	123.05 (15)	C14—C13—C12	120.23 (16)
C4—C5—Cl1	118.89 (13)	C14—C13—H13A	119.9
C6—C5—Cl1	118.06 (13)	C12—C13—H13A	119.9
C1—C6—C5	118.11 (14)	C13—C14—C9	119.99 (15)
C1—C6—H6A	120.9	C13—C14—H14A	120.0
C5—C6—H6A	120.9	C9—C14—H14A	120.0
C7—N1—C1—C6	5.6 (3)	C8—N2—C7—S1	174.92 (12)
C7—N1—C1—C2	−174.92 (16)	C7—N2—C8—O1	6.5 (3)
C6—C1—C2—C3	−0.2 (2)	C7—N2—C8—C9	−171.93 (14)
N1—C1—C2—C3	−179.71 (15)	O1—C8—C9—C14	160.55 (16)
C1—C2—C3—C4	0.4 (3)	N2—C8—C9—C14	−21.0 (2)
C2—C3—C4—C5	−0.4 (3)	O1—C8—C9—C10	−20.0 (2)
C3—C4—C5—C6	0.1 (3)	N2—C8—C9—C10	158.45 (14)
C3—C4—C5—Cl1	179.77 (13)	C14—C9—C10—C11	1.4 (2)
C2—C1—C6—C5	−0.1 (2)	C8—C9—C10—C11	−178.14 (15)
N1—C1—C6—C5	179.36 (15)	C9—C10—C11—C12	−0.7 (3)
C4—C5—C6—C1	0.2 (2)	C10—C11—C12—C13	0.0 (3)
Cl1—C5—C6—C1	−179.53 (12)	C11—C12—C13—C14	0.1 (3)
C1—N1—C7—N2	178.25 (15)	C12—C13—C14—C9	0.5 (3)
C1—N1—C7—S1	−0.4 (3)	C10—C9—C14—C13	−1.3 (2)
C8—N2—C7—N1	−3.9 (2)	C8—C9—C14—C13	178.21 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.88	1.83	2.592 (2)	143
N2—H2B···S1^i	0.88	2.82	3.607 (1)	150
C14—H14A···S1^i	0.95	2.76	3.330 (2)	119

Symmetry code: (i) −x+2, −y+1, −z.