N-(3,4-Dichloro­phen­yl)-N′-(phenyl­acetyl)­thio­urea

The mol­ecule in the title compound, C₁₅H₁₂Cl₂N₂OS, adopts a trans–cis configuration with respect to the positions of the phenyl­acetyl and 3,4-dichloro­phenyl groups relative to the S atom across their C—N bonds. In the crystal structure, the mol­ecules are linked by N—H...O and C—H...O inter­actions, forming a chain along the c axis.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C)= 0.003 Å
• R factor = 0.035
• wR factor = 0.093
• Data-to-parameter ratio = 15.0

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

N-(3,4-Dichlorophenyl)-N'-phenylacetylthiourea

Crystal data

C15H12Cl2N2OS	F(000) = 696
Mr = 339.23	Dx = 1.471 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 977 reflections
a = 8.139 (2) Å	θ = 2.0–25.5°
b = 20.381 (5) Å	µ = 0.56 mm^−1
c = 9.476 (3) Å	T = 298 K
β = 103.070 (4)°	Block, colourless
V = 1531.3 (7) Å^3	0.48 × 0.31 × 0.25 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer	2854 independent reflections
Radiation source: fine-focus sealed tube	2337 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
Detector resolution: 83.66 pixels mm^-1	θmax = 25.5°, θmin = 2.0°
ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −24→18
Tmin = 0.775, Tmax = 0.873	l = −10→11
8052 measured reflections

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.093	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0453P)^2 + 0.4844P] where P = (Fo^2 + 2Fc^2)/3
2854 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.40 e Å^−3
0 restraints	Δρmin = −0.36 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	0.11065 (9)	0.37416 (3)	−0.16585 (7)	0.0709 (2)
Cl2	0.26369 (10)	0.48893 (3)	−0.32452 (7)	0.0763 (2)
S1	0.35864 (8)	0.60519 (3)	0.41707 (5)	0.05285 (18)
O1	0.51125 (17)	0.72743 (7)	0.06593 (13)	0.0445 (3)
N1	0.48723 (19)	0.70163 (8)	0.29409 (16)	0.0371 (4)
H1	0.5093	0.7162	0.3815	0.045*
N2	0.3815 (2)	0.61730 (8)	0.13868 (17)	0.0439 (4)
H2	0.4129	0.6438	0.0793	0.053*
C1	0.8262 (3)	0.84776 (11)	0.1159 (2)	0.0460 (5)
H1A	0.7385	0.8700	0.0547	0.055*
C2	0.9884 (3)	0.85248 (13)	0.0942 (2)	0.0599 (6)
H2A	1.0093	0.8781	0.0190	0.072*
C3	1.1172 (3)	0.81969 (14)	0.1825 (3)	0.0667 (7)
H3	1.2259	0.8226	0.1671	0.080*
C4	1.0869 (3)	0.78219 (13)	0.2944 (3)	0.0674 (7)
H4	1.1750	0.7597	0.3545	0.081*
C5	0.9260 (3)	0.77782 (11)	0.3177 (2)	0.0519 (5)
H5	0.9065	0.7529	0.3944	0.062*
C6	0.7938 (2)	0.81014 (9)	0.22791 (19)	0.0378 (4)
C7	0.6178 (2)	0.80499 (10)	0.2532 (2)	0.0419 (5)
H7A	0.6228	0.8079	0.3562	0.050*
H7B	0.5506	0.8414	0.2060	0.050*
C8	0.5347 (2)	0.74153 (9)	0.19544 (19)	0.0359 (4)
C9	0.4075 (2)	0.63997 (9)	0.27462 (19)	0.0369 (4)
C10	0.3124 (3)	0.55825 (9)	0.0750 (2)	0.0407 (4)
C11	0.2432 (3)	0.50874 (10)	0.1437 (2)	0.0514 (5)
H11	0.2389	0.5129	0.2405	0.062*
C12	0.1810 (3)	0.45343 (10)	0.0667 (2)	0.0537 (6)
H12	0.1335	0.4205	0.1125	0.064*
C13	0.1873 (3)	0.44563 (10)	−0.0760 (2)	0.0476 (5)
C14	0.2547 (3)	0.49518 (10)	−0.1452 (2)	0.0463 (5)
C15	0.3166 (3)	0.55084 (10)	−0.0697 (2)	0.0454 (5)
H15	0.3620	0.5841	−0.1163	0.054*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0938 (5)	0.0420 (3)	0.0707 (4)	−0.0099 (3)	0.0055 (3)	−0.0147 (3)
Cl2	0.1215 (6)	0.0666 (4)	0.0446 (3)	−0.0098 (4)	0.0265 (3)	−0.0163 (3)
S1	0.0741 (4)	0.0536 (3)	0.0358 (3)	−0.0180 (3)	0.0229 (3)	0.0002 (2)
O1	0.0636 (9)	0.0437 (8)	0.0291 (7)	−0.0101 (7)	0.0163 (6)	−0.0018 (6)
N1	0.0474 (9)	0.0377 (9)	0.0282 (7)	−0.0053 (7)	0.0130 (7)	−0.0032 (6)
N2	0.0644 (11)	0.0379 (9)	0.0319 (8)	−0.0119 (8)	0.0158 (8)	0.0005 (7)
C1	0.0480 (12)	0.0521 (13)	0.0380 (11)	−0.0089 (10)	0.0101 (9)	0.0003 (9)
C2	0.0586 (14)	0.0731 (17)	0.0521 (13)	−0.0209 (13)	0.0216 (12)	−0.0040 (12)
C3	0.0454 (13)	0.0804 (18)	0.0780 (17)	−0.0138 (13)	0.0214 (13)	−0.0155 (15)
C4	0.0503 (14)	0.0655 (16)	0.0797 (18)	0.0061 (12)	0.0011 (13)	−0.0039 (14)
C5	0.0616 (14)	0.0424 (12)	0.0510 (12)	−0.0018 (10)	0.0116 (10)	0.0041 (10)
C6	0.0460 (11)	0.0339 (10)	0.0344 (10)	−0.0058 (8)	0.0108 (8)	−0.0071 (8)
C7	0.0516 (11)	0.0394 (11)	0.0389 (10)	−0.0045 (9)	0.0189 (9)	−0.0049 (8)
C8	0.0379 (10)	0.0378 (10)	0.0342 (10)	−0.0001 (8)	0.0129 (8)	0.0003 (8)
C9	0.0403 (10)	0.0383 (10)	0.0336 (10)	−0.0014 (8)	0.0116 (8)	−0.0001 (8)
C10	0.0501 (11)	0.0355 (10)	0.0360 (10)	−0.0028 (9)	0.0090 (8)	0.0003 (8)
C11	0.0729 (14)	0.0430 (12)	0.0384 (11)	−0.0096 (11)	0.0127 (10)	0.0029 (9)
C12	0.0732 (15)	0.0381 (12)	0.0491 (13)	−0.0078 (11)	0.0123 (11)	0.0056 (10)
C13	0.0552 (12)	0.0345 (11)	0.0485 (12)	0.0020 (9)	0.0018 (10)	−0.0043 (9)
C14	0.0570 (12)	0.0436 (12)	0.0367 (10)	0.0038 (10)	0.0073 (9)	−0.0034 (9)
C15	0.0616 (13)	0.0385 (11)	0.0380 (11)	−0.0027 (10)	0.0152 (9)	0.0013 (9)

Geometric parameters (Å, º)

Cl1—C13	1.731 (2)	C4—C5	1.379 (3)
Cl2—C14	1.722 (2)	C4—H4	0.9300
S1—C9	1.6509 (18)	C5—C6	1.379 (3)
O1—C8	1.233 (2)	C5—H5	0.9300
N1—C8	1.359 (2)	C6—C7	1.509 (3)
N1—C9	1.407 (2)	C7—C8	1.504 (3)
N1—H1	0.8600	C7—H7A	0.9700
N2—C9	1.340 (2)	C7—H7B	0.9700
N2—C10	1.405 (2)	C10—C15	1.387 (3)
N2—H2	0.8600	C10—C11	1.387 (3)
C1—C6	1.382 (3)	C11—C12	1.375 (3)
C1—C2	1.385 (3)	C11—H11	0.9300
C1—H1A	0.9300	C12—C13	1.374 (3)
C2—C3	1.360 (4)	C12—H12	0.9300
C2—H2A	0.9300	C13—C14	1.383 (3)
C3—C4	1.374 (4)	C14—C15	1.375 (3)
C3—H3	0.9300	C15—H15	0.9300
C8—N1—C9	129.68 (15)	C8—C7—H7B	109.3
C8—N1—H1	115.2	C6—C7—H7B	109.3
C9—N1—H1	115.2	H7A—C7—H7B	108.0
C9—N2—C10	132.00 (16)	O1—C8—N1	122.77 (17)
C9—N2—H2	114.0	O1—C8—C7	121.20 (16)
C10—N2—H2	114.0	N1—C8—C7	116.03 (15)
C6—C1—C2	120.4 (2)	N2—C9—N1	113.69 (15)
C6—C1—H1A	119.8	N2—C9—S1	128.56 (15)
C2—C1—H1A	119.8	N1—C9—S1	117.74 (13)
C3—C2—C1	120.2 (2)	C15—C10—C11	119.18 (19)
C3—C2—H2A	119.9	C15—C10—N2	114.89 (17)
C1—C2—H2A	119.9	C11—C10—N2	125.93 (18)
C2—C3—C4	120.0 (2)	C12—C11—C10	119.2 (2)
C2—C3—H3	120.0	C12—C11—H11	120.4
C4—C3—H3	120.0	C10—C11—H11	120.4
C3—C4—C5	120.1 (2)	C13—C12—C11	121.7 (2)
C3—C4—H4	119.9	C13—C12—H12	119.1
C5—C4—H4	119.9	C11—C12—H12	119.1
C6—C5—C4	120.5 (2)	C12—C13—C14	119.27 (19)
C6—C5—H5	119.8	C12—C13—Cl1	119.47 (17)
C4—C5—H5	119.8	C14—C13—Cl1	121.26 (17)
C5—C6—C1	118.76 (19)	C15—C14—C13	119.59 (19)
C5—C6—C7	120.36 (18)	C15—C14—Cl2	118.84 (17)
C1—C6—C7	120.88 (18)	C13—C14—Cl2	121.57 (16)
C8—C7—C6	111.56 (15)	C14—C15—C10	121.09 (19)
C8—C7—H7A	109.3	C14—C15—H15	119.5
C6—C7—H7A	109.3	C10—C15—H15	119.5
C6—C1—C2—C3	0.5 (3)	C8—N1—C9—S1	−177.32 (15)
C1—C2—C3—C4	−0.6 (4)	C9—N2—C10—C15	−176.0 (2)
C2—C3—C4—C5	−0.2 (4)	C9—N2—C10—C11	3.9 (4)
C3—C4—C5—C6	1.0 (4)	C15—C10—C11—C12	0.2 (3)
C4—C5—C6—C1	−1.0 (3)	N2—C10—C11—C12	−179.7 (2)
C4—C5—C6—C7	179.7 (2)	C10—C11—C12—C13	0.7 (4)
C2—C1—C6—C5	0.3 (3)	C11—C12—C13—C14	−1.4 (3)
C2—C1—C6—C7	179.61 (19)	C11—C12—C13—Cl1	178.75 (18)
C5—C6—C7—C8	−79.4 (2)	C12—C13—C14—C15	1.0 (3)
C1—C6—C7—C8	101.4 (2)	Cl1—C13—C14—C15	−179.08 (16)
C9—N1—C8—O1	0.2 (3)	C12—C13—C14—Cl2	−179.12 (17)
C9—N1—C8—C7	179.88 (18)	Cl1—C13—C14—Cl2	0.8 (3)
C6—C7—C8—O1	−60.4 (2)	C13—C14—C15—C10	−0.1 (3)
C6—C7—C8—N1	119.95 (18)	Cl2—C14—C15—C10	−179.95 (16)
C10—N2—C9—N1	177.62 (19)	C11—C10—C15—C14	−0.5 (3)
C10—N2—C9—S1	−2.3 (3)	N2—C10—C15—C14	179.39 (19)
C8—N1—C9—N2	2.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.86	1.90	2.638 (2)	143
C11—H11···S1	0.93	2.56	3.218 (2)	128
N1—H1···O1^i	0.86	2.09	2.922 (2)	163
C7—H7A···O1^i	0.97	2.47	3.337 (2)	148

Symmetry code: (i) x, −y+3/2, z+1/2.