1-(4-Chloro­phen­yl)-3-(4-methyl­benzo­yl)thio­urea

Saeed, A.; Flörke, U.

doi:10.1107/S1600536806022501

1-(4-Chlorophenyl)-3-(4-methylbenzoyl)thiourea

In the structure of the title compound, C₁₅H₁₃ClN₂OS, the dihedral angle between the two aromatic ring planes is 30.46 (8)°. Intermolecular N—H

S hydrogen bonds link the molecules into dimeric units which are stacked along [010].

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806022501/om2022sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806022501/om2022Isup2.hkl Contains datablock I

CCDC reference: 613796

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Key indicators

Single-crystal X-ray study
T = 120 K
Mean (C-C)= 0.003 Å
R factor = 0.043
wR factor = 0.109
Data-to-parameter ratio = 18.8

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No errors found in this datablock

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-(4-Chlorophenyl)-3-(4-methylbenzoyl)thiourea top

Crystal data top

C₁₅H₁₃ClN₂OS	F(000) = 632
M_r = 304.78	D_x = 1.443 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3569 reflections
a = 12.0097 (8) Å	θ = 2.2–28.1°
b = 6.3118 (4) Å	µ = 0.42 mm⁻¹
c = 18.8101 (13) Å	T = 120 K
β = 100.337 (1)°	Plate, colorless
V = 1402.72 (16) Å³	0.48 × 0.24 × 0.09 mm
Z = 4

Data collection top

Bruker SMART APEX-I diffractometer	3401 independent reflections
Radiation source: sealed tube	2905 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
φ and ω scans	θ_max = 28.1°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −14→15
T_min = 0.825, T_max = 0.963	k = −8→8
13563 measured reflections	l = −24→24

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)] = 0.043	Hydrogen site location: difference Fourier map
wR(F²) = 0.109	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0577P)² + 0.5904P] where P = (F_o² + 2F_c²)/3
3401 reflections	(Δ/σ)_max < 0.001
181 parameters	Δρ_max = 0.49 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Special details top

Experimental. ¹H NMR (CDCl₃): δ 2.43 (3H, s, ArCH₃), 7.31–7.75 (aromatic), 9.19 (1H, s, broad, NH), 12.76 (1H, s, broad, NH); ¹³C NMR (CDCl₃): δ 23.9 (CH₃), 126.2 (4 CH), 129.0 (2 CH), 129.20 (2CH), 130.7 (C), 132.1 (C), 134.8 (C), 142.3 (C), 168.1 (C═O), 178.4 (C═S). EIMS m/e: 304, 306, 168.9,126, 119, 91, 64.9.

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	0.48119 (5)	0.01325 (7)	0.19470 (3)	0.03474 (15)
S1	0.09352 (4)	0.85729 (8)	0.08769 (2)	0.02765 (14)
O1	0.34926 (11)	1.0711 (2)	−0.04939 (7)	0.0289 (3)
N1	0.29415 (12)	0.7946 (2)	0.04500 (7)	0.0203 (3)
H1A	0.3420	0.8504	0.0199	0.024*
N2	0.18287 (13)	1.0696 (2)	−0.00688 (8)	0.0210 (3)
H2B	0.1172	1.1347	−0.0115	0.025*
C1	0.33294 (15)	0.6059 (3)	0.08288 (9)	0.0192 (3)
C2	0.26801 (16)	0.4793 (3)	0.11994 (10)	0.0259 (4)
H2A	0.1923	0.5181	0.1221	0.031*
C3	0.31430 (17)	0.2959 (3)	0.15380 (10)	0.0274 (4)
H3A	0.2707	0.2100	0.1800	0.033*
C4	0.42318 (16)	0.2387 (3)	0.14937 (9)	0.0230 (4)
C5	0.48776 (16)	0.3606 (3)	0.11171 (10)	0.0269 (4)
H5A	0.5625	0.3182	0.1082	0.032*
C6	0.44256 (15)	0.5460 (3)	0.07896 (10)	0.0243 (4)
H6A	0.4871	0.6325	0.0537	0.029*
C7	0.19736 (14)	0.9009 (3)	0.04119 (9)	0.0198 (3)
C8	0.25655 (15)	1.1501 (3)	−0.04845 (9)	0.0208 (3)
C9	0.21392 (14)	1.3399 (3)	−0.09208 (9)	0.0191 (3)
C10	0.13269 (15)	1.4750 (3)	−0.07303 (9)	0.0214 (4)
H10A	0.1024	1.4475	−0.0307	0.026*
C11	0.09570 (15)	1.6494 (3)	−0.11535 (9)	0.0221 (4)
H11A	0.0395	1.7394	−0.1020	0.027*
C12	0.13973 (15)	1.6949 (3)	−0.17722 (9)	0.0219 (4)
C13	0.22205 (16)	1.5610 (3)	−0.19544 (9)	0.0254 (4)
H13A	0.2536	1.5906	−0.2372	0.031*
C14	0.25896 (15)	1.3849 (3)	−0.15374 (9)	0.0234 (4)
H14A	0.3150	1.2947	−0.1672	0.028*
C15	0.09912 (19)	1.8846 (3)	−0.22293 (10)	0.0313 (4)
H15A	0.0494	1.9703	−0.1985	0.047*
H15B	0.0573	1.8373	−0.2698	0.047*
H15C	0.1643	1.9699	−0.2303	0.047*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0455 (3)	0.0221 (2)	0.0341 (3)	0.0093 (2)	0.0004 (2)	0.00809 (18)
S1	0.0260 (3)	0.0308 (3)	0.0290 (2)	0.00797 (18)	0.01258 (18)	0.01063 (18)
O1	0.0230 (7)	0.0272 (7)	0.0382 (7)	0.0045 (5)	0.0099 (6)	0.0108 (6)
N1	0.0202 (7)	0.0185 (7)	0.0231 (7)	0.0001 (6)	0.0062 (6)	0.0048 (6)
N2	0.0217 (7)	0.0178 (7)	0.0242 (7)	0.0040 (6)	0.0062 (6)	0.0037 (6)
C1	0.0227 (8)	0.0154 (7)	0.0185 (7)	0.0004 (6)	0.0013 (6)	0.0010 (6)
C2	0.0250 (9)	0.0222 (9)	0.0311 (9)	0.0018 (7)	0.0067 (7)	0.0062 (7)
C3	0.0337 (10)	0.0219 (9)	0.0273 (9)	−0.0035 (7)	0.0069 (8)	0.0049 (7)
C4	0.0320 (10)	0.0146 (8)	0.0197 (8)	0.0027 (7)	−0.0028 (7)	−0.0003 (6)
C5	0.0243 (9)	0.0227 (9)	0.0326 (9)	0.0048 (7)	0.0019 (7)	0.0005 (7)
C6	0.0247 (9)	0.0211 (8)	0.0277 (9)	0.0002 (7)	0.0064 (7)	0.0033 (7)
C7	0.0222 (8)	0.0162 (8)	0.0207 (8)	0.0001 (6)	0.0034 (6)	0.0000 (6)
C8	0.0220 (8)	0.0181 (8)	0.0226 (8)	−0.0012 (6)	0.0049 (6)	0.0012 (6)
C9	0.0217 (8)	0.0150 (7)	0.0200 (7)	−0.0006 (6)	0.0020 (6)	0.0004 (6)
C10	0.0278 (9)	0.0171 (8)	0.0203 (8)	−0.0011 (7)	0.0071 (7)	−0.0003 (6)
C11	0.0257 (9)	0.0170 (8)	0.0236 (8)	0.0019 (7)	0.0042 (7)	−0.0036 (6)
C12	0.0285 (9)	0.0159 (8)	0.0196 (8)	−0.0023 (7)	−0.0009 (7)	−0.0011 (6)
C13	0.0311 (10)	0.0245 (9)	0.0216 (8)	−0.0001 (7)	0.0070 (7)	0.0024 (7)
C14	0.0245 (9)	0.0212 (9)	0.0256 (8)	0.0019 (7)	0.0076 (7)	0.0000 (7)
C15	0.0475 (12)	0.0216 (9)	0.0249 (9)	0.0058 (8)	0.0067 (8)	0.0043 (7)

Geometric parameters (Å, º) top

Cl1—C4	1.7393 (17)	C5—H5A	0.9500
S1—C7	1.6696 (18)	C6—H6A	0.9500
O1—C8	1.223 (2)	C8—C9	1.490 (2)
N1—C7	1.333 (2)	C9—C10	1.390 (2)
N1—C1	1.422 (2)	C9—C14	1.394 (2)
N1—H1A	0.8800	C10—C11	1.384 (2)
N2—C8	1.379 (2)	C10—H10A	0.9500
N2—C7	1.388 (2)	C11—C12	1.392 (2)
N2—H2B	0.8800	C11—H11A	0.9500
C1—C6	1.384 (2)	C12—C13	1.389 (3)
C1—C2	1.388 (2)	C12—C15	1.504 (2)
C2—C3	1.389 (2)	C13—C14	1.386 (2)
C2—H2A	0.9500	C13—H13A	0.9500
C3—C4	1.373 (3)	C14—H14A	0.9500
C3—H3A	0.9500	C15—H15A	0.9800
C4—C5	1.376 (3)	C15—H15B	0.9800
C5—C6	1.387 (2)	C15—H15C	0.9800

C7—N1—C1	130.71 (15)	O1—C8—N2	122.47 (16)
C7—N1—H1A	114.6	O1—C8—C9	122.92 (15)
C1—N1—H1A	114.6	N2—C8—C9	114.61 (15)
C8—N2—C7	129.34 (15)	C10—C9—C14	118.98 (15)
C8—N2—H2B	115.3	C10—C9—C8	122.61 (15)
C7—N2—H2B	115.3	C14—C9—C8	118.40 (15)
C6—C1—C2	119.65 (16)	C11—C10—C9	120.48 (16)
C6—C1—N1	115.53 (15)	C11—C10—H10A	119.8
C2—C1—N1	124.78 (16)	C9—C10—H10A	119.8
C1—C2—C3	119.70 (17)	C10—C11—C12	120.92 (16)
C1—C2—H2A	120.1	C10—C11—H11A	119.5
C3—C2—H2A	120.1	C12—C11—H11A	119.5
C4—C3—C2	119.89 (17)	C13—C12—C11	118.35 (16)
C4—C3—H3A	120.1	C13—C12—C15	121.03 (16)
C2—C3—H3A	120.1	C11—C12—C15	120.62 (16)
C3—C4—C5	121.03 (16)	C14—C13—C12	121.16 (16)
C3—C4—Cl1	119.15 (14)	C14—C13—H13A	119.4
C5—C4—Cl1	119.79 (14)	C12—C13—H13A	119.4
C4—C5—C6	119.25 (17)	C13—C14—C9	120.10 (16)
C4—C5—H5A	120.4	C13—C14—H14A	120.0
C6—C5—H5A	120.4	C9—C14—H14A	120.0
C1—C6—C5	120.46 (17)	C12—C15—H15A	109.5
C1—C6—H6A	119.8	C12—C15—H15B	109.5
C5—C6—H6A	119.8	H15A—C15—H15B	109.5
N1—C7—N2	115.31 (15)	C12—C15—H15C	109.5
N1—C7—S1	127.95 (13)	H15A—C15—H15C	109.5
N2—C7—S1	116.73 (12)	H15B—C15—H15C	109.5

C7—N1—C1—C6	−175.68 (17)	C7—N2—C8—O1	2.5 (3)
C7—N1—C1—C2	6.7 (3)	C7—N2—C8—C9	−177.62 (16)
C6—C1—C2—C3	1.1 (3)	O1—C8—C9—C10	−155.54 (18)
N1—C1—C2—C3	178.67 (16)	N2—C8—C9—C10	24.6 (2)
C1—C2—C3—C4	−1.2 (3)	O1—C8—C9—C14	23.4 (3)
C2—C3—C4—C5	0.0 (3)	N2—C8—C9—C14	−156.45 (16)
C2—C3—C4—Cl1	177.84 (14)	C14—C9—C10—C11	1.1 (3)
C3—C4—C5—C6	1.2 (3)	C8—C9—C10—C11	−179.96 (15)
Cl1—C4—C5—C6	−176.63 (14)	C9—C10—C11—C12	−0.8 (3)
C2—C1—C6—C5	0.1 (3)	C10—C11—C12—C13	−0.1 (3)
N1—C1—C6—C5	−177.69 (15)	C10—C11—C12—C15	179.99 (16)
C4—C5—C6—C1	−1.2 (3)	C11—C12—C13—C14	0.7 (3)
C1—N1—C7—N2	−174.03 (15)	C15—C12—C13—C14	−179.43 (17)
C1—N1—C7—S1	6.8 (3)	C12—C13—C14—C9	−0.3 (3)
C8—N2—C7—N1	−3.8 (3)	C10—C9—C14—C13	−0.6 (3)
C8—N2—C7—S1	175.44 (14)	C8—C9—C14—C13	−179.53 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.88	1.92	2.6567 (19)	140
N2—H2B···S1ⁱ	0.88	2.68	3.4250 (15)	144

Symmetry code: (i) −x, −y+2, −z.

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1-(4-Chloro­phen­yl)-3-(4-methyl­benzo­yl)thio­urea

Supporting information

Key indicators

checkCIF/PLATON results

1-(4-Chlorophenyl)-3-(4-methylbenzoyl)thiourea