N-(2-Chloro­phenyl)-N′-(4-methoxy­benzoyl)­thio­urea

In the title compound, C₁₅H₁₃ClN₂O₂S, the dihedral angle between the 2-chloro­phenyl and 4-methoxy­phenyl groups is 54.12 (13)°. The mol­ecule is stabil­ized by intermolecular C—H...S and N—H...S interactions, forming double-column chains arranged parallel to the b axis.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.059
• wR factor = 0.140
• Data-to-parameter ratio = 16.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT414_ALERT_2_C Short Intra D-H..H-X       H1     ..  H1A     ..       1.99 Ang.
PLAT420_ALERT_2_C D-H Without Acceptor       N1     -   H1     ...          ?

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); 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-(2-Chlorophenyl)-N-(4-methoxybenzoyl)thiourea

Crystal data

C15H13ClN2O2S	F(000) = 664
Mr = 320.78	Dx = 1.453 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 13.438 (3) Å	Cell parameters from 2167 reflections
b = 3.9893 (9) Å	θ = 1.5–27.0°
c = 27.727 (6) Å	µ = 0.41 mm^−1
β = 99.508 (4)°	T = 273 K
V = 1466.0 (5) Å^3	Block, colourless
Z = 4	0.22 × 0.19 × 0.16 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer	3162 independent reflections
Radiation source: fine-focus sealed tube	2649 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
Detector resolution: 83.66 pixels mm^-1	θmax = 27.0°, θmin = 1.5°
ω scans	h = −13→17
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −5→5
Tmin = 0.916, Tmax = 0.938	l = −35→27
7879 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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.140	H-atom parameters constrained
S = 1.19	w = 1/[σ^2(Fo^2) + (0.0589P)^2 + 0.3777P] where P = (Fo^2 + 2Fc^2)/3
3162 reflections	(Δ/σ)max = 0.001
191 parameters	Δρmax = 0.33 e Å^−3
0 restraints	Δρmin = −0.18 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.41573 (6)	−0.2117 (2)	0.04847 (3)	0.0738 (3)
S1	0.19169 (4)	−0.16876 (18)	0.18381 (2)	0.0447 (2)
O1	0.51528 (14)	0.1285 (6)	0.17833 (7)	0.0692 (6)
O2	0.74579 (13)	−0.0232 (6)	0.39513 (6)	0.0591 (5)
N1	0.38261 (14)	−0.0358 (6)	0.21388 (7)	0.0447 (5)
H1	0.3662	−0.0932	0.2414	0.054*
N2	0.32877 (15)	0.0564 (6)	0.13186 (7)	0.0461 (5)
H2	0.3907	0.1115	0.1321	0.055*
C1	0.52146 (17)	−0.1171 (6)	0.30500 (9)	0.0431 (6)
H1A	0.4575	−0.2097	0.3034	0.052*
C2	0.58848 (19)	−0.1278 (7)	0.34809 (9)	0.0479 (6)
H2A	0.5693	−0.2264	0.3755	0.057*
C3	0.68438 (17)	0.0068 (7)	0.35105 (8)	0.0425 (6)
C4	0.71249 (18)	0.1590 (7)	0.31041 (9)	0.0434 (6)
H4	0.7762	0.2540	0.3122	0.052*
C5	0.64447 (17)	0.1672 (7)	0.26735 (9)	0.0435 (6)
H5	0.6636	0.2670	0.2400	0.052*
C6	0.54857 (17)	0.0317 (6)	0.26356 (8)	0.0391 (5)
C7	0.48254 (18)	0.0471 (7)	0.21546 (9)	0.0456 (6)
C8	0.30453 (17)	−0.0402 (6)	0.17439 (8)	0.0394 (5)
C9	0.26362 (18)	0.0783 (6)	0.08634 (8)	0.0410 (6)
C10	0.29672 (19)	−0.0371 (7)	0.04432 (9)	0.0484 (6)
C11	0.2368 (2)	−0.0077 (8)	−0.00068 (9)	0.0596 (7)
H11	0.2599	−0.0835	−0.0286	0.072*
C12	0.1427 (2)	0.1335 (9)	−0.00446 (10)	0.0639 (8)
H12	0.1018	0.1509	−0.0349	0.077*
C13	0.1088 (2)	0.2491 (8)	0.03648 (10)	0.0591 (8)
H13	0.0449	0.3437	0.0338	0.071*
C14	0.16971 (19)	0.2252 (7)	0.08169 (9)	0.0495 (6)
H14	0.1471	0.3090	0.1092	0.059*
C15	0.8456 (2)	0.1038 (9)	0.39970 (10)	0.0648 (9)
H15A	0.8808	−0.0104	0.3771	0.097*
H15B	0.8801	0.0681	0.4325	0.097*
H15C	0.8433	0.3394	0.3926	0.097*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0559 (4)	0.1049 (7)	0.0652 (5)	0.0132 (4)	0.0234 (4)	−0.0060 (4)
S1	0.0371 (3)	0.0562 (4)	0.0415 (3)	−0.0043 (3)	0.0086 (2)	0.0024 (3)
O1	0.0446 (10)	0.123 (2)	0.0415 (10)	−0.0171 (11)	0.0107 (8)	0.0116 (11)
O2	0.0448 (10)	0.0889 (15)	0.0420 (10)	−0.0067 (10)	0.0023 (8)	0.0063 (10)
N1	0.0359 (10)	0.0672 (15)	0.0320 (10)	−0.0029 (10)	0.0087 (8)	0.0005 (9)
N2	0.0365 (10)	0.0672 (15)	0.0359 (10)	−0.0049 (10)	0.0096 (8)	0.0027 (10)
C1	0.0337 (12)	0.0491 (15)	0.0487 (14)	−0.0031 (10)	0.0130 (10)	0.0010 (11)
C2	0.0440 (14)	0.0608 (17)	0.0417 (13)	−0.0015 (12)	0.0152 (11)	0.0093 (12)
C3	0.0401 (12)	0.0494 (15)	0.0381 (12)	0.0015 (11)	0.0066 (10)	−0.0040 (11)
C4	0.0345 (12)	0.0520 (15)	0.0456 (13)	−0.0046 (11)	0.0123 (10)	−0.0051 (11)
C5	0.0385 (12)	0.0530 (15)	0.0421 (13)	−0.0037 (11)	0.0153 (10)	0.0010 (11)
C6	0.0353 (12)	0.0449 (14)	0.0388 (12)	−0.0003 (10)	0.0112 (9)	−0.0021 (10)
C7	0.0383 (12)	0.0585 (17)	0.0417 (13)	−0.0021 (12)	0.0114 (10)	−0.0011 (12)
C8	0.0383 (12)	0.0439 (14)	0.0372 (12)	0.0013 (10)	0.0094 (10)	−0.0037 (10)
C9	0.0419 (13)	0.0449 (15)	0.0364 (12)	−0.0051 (10)	0.0065 (10)	0.0031 (10)
C10	0.0487 (14)	0.0564 (17)	0.0419 (13)	−0.0022 (12)	0.0126 (11)	0.0013 (12)
C11	0.0739 (19)	0.070 (2)	0.0365 (13)	−0.0073 (16)	0.0129 (13)	−0.0019 (13)
C12	0.0679 (19)	0.077 (2)	0.0413 (15)	−0.0043 (16)	−0.0072 (13)	0.0094 (14)
C13	0.0568 (17)	0.064 (2)	0.0541 (16)	0.0059 (14)	0.0011 (13)	0.0130 (14)
C14	0.0510 (15)	0.0549 (17)	0.0436 (14)	0.0053 (12)	0.0109 (11)	0.0038 (12)
C15	0.0448 (15)	0.090 (3)	0.0564 (17)	−0.0103 (15)	−0.0017 (13)	−0.0012 (16)

Geometric parameters (Å, º)

Cl1—C10	1.731 (3)	C4—H4	0.9300
S1—C8	1.662 (2)	C5—C6	1.385 (3)
O1—C7	1.228 (3)	C5—H5	0.9300
O2—C3	1.362 (3)	C6—C7	1.476 (3)
O2—C15	1.419 (3)	C9—C14	1.378 (3)
N1—C7	1.377 (3)	C9—C10	1.392 (3)
N1—C8	1.386 (3)	C10—C11	1.374 (4)
N1—H1	0.8600	C11—C12	1.372 (4)
N2—C8	1.331 (3)	C11—H11	0.9300
N2—C9	1.415 (3)	C12—C13	1.371 (4)
N2—H2	0.8600	C12—H12	0.9300
C1—C2	1.373 (3)	C13—C14	1.382 (4)
C1—C6	1.394 (3)	C13—H13	0.9300
C1—H1A	0.9300	C14—H14	0.9300
C2—C3	1.386 (3)	C15—H15A	0.9600
C2—H2A	0.9300	C15—H15B	0.9600
C3—C4	1.386 (3)	C15—H15C	0.9600
C4—C5	1.379 (3)
C3—O2—C15	118.2 (2)	N2—C8—N1	115.6 (2)
C7—N1—C8	129.5 (2)	N2—C8—S1	126.28 (18)
C7—N1—H1	115.3	N1—C8—S1	118.11 (16)
C8—N1—H1	115.3	C14—C9—C10	118.5 (2)
C8—N2—C9	127.0 (2)	C14—C9—N2	122.1 (2)
C8—N2—H2	116.5	C10—C9—N2	119.3 (2)
C9—N2—H2	116.5	C11—C10—C9	120.8 (3)
C2—C1—C6	120.5 (2)	C11—C10—Cl1	119.4 (2)
C2—C1—H1A	119.8	C9—C10—Cl1	119.80 (19)
C6—C1—H1A	119.8	C12—C11—C10	119.9 (3)
C1—C2—C3	120.6 (2)	C12—C11—H11	120.0
C1—C2—H2A	119.7	C10—C11—H11	120.0
C3—C2—H2A	119.7	C13—C12—C11	120.2 (2)
O2—C3—C2	116.0 (2)	C13—C12—H12	119.9
O2—C3—C4	124.2 (2)	C11—C12—H12	119.9
C2—C3—C4	119.8 (2)	C12—C13—C14	120.0 (3)
C5—C4—C3	118.9 (2)	C12—C13—H13	120.0
C5—C4—H4	120.5	C14—C13—H13	120.0
C3—C4—H4	120.5	C9—C14—C13	120.7 (3)
C4—C5—C6	122.1 (2)	C9—C14—H14	119.7
C4—C5—H5	118.9	C13—C14—H14	119.7
C6—C5—H5	118.9	O2—C15—H15A	109.5
C5—C6—C1	118.0 (2)	O2—C15—H15B	109.5
C5—C6—C7	117.7 (2)	H15A—C15—H15B	109.5
C1—C6—C7	124.2 (2)	O2—C15—H15C	109.5
O1—C7—N1	121.3 (2)	H15A—C15—H15C	109.5
O1—C7—C6	121.6 (2)	H15B—C15—H15C	109.5
N1—C7—C6	117.2 (2)
C6—C1—C2—C3	−0.4 (4)	C9—N2—C8—N1	−179.3 (2)
C15—O2—C3—C2	178.6 (3)	C9—N2—C8—S1	1.8 (4)
C15—O2—C3—C4	−1.2 (4)	C7—N1—C8—N2	−1.6 (4)
C1—C2—C3—O2	−178.6 (2)	C7—N1—C8—S1	177.4 (2)
C1—C2—C3—C4	1.1 (4)	C8—N2—C9—C14	46.2 (4)
O2—C3—C4—C5	178.5 (2)	C8—N2—C9—C10	−137.0 (3)
C2—C3—C4—C5	−1.2 (4)	C14—C9—C10—C11	−0.6 (4)
C3—C4—C5—C6	0.8 (4)	N2—C9—C10—C11	−177.5 (3)
C4—C5—C6—C1	−0.1 (4)	C14—C9—C10—Cl1	178.1 (2)
C4—C5—C6—C7	−178.6 (2)	N2—C9—C10—Cl1	1.2 (3)
C2—C1—C6—C5	−0.1 (4)	C9—C10—C11—C12	−0.7 (5)
C2—C1—C6—C7	178.4 (2)	Cl1—C10—C11—C12	−179.3 (2)
C8—N1—C7—O1	−1.1 (5)	C10—C11—C12—C13	0.8 (5)
C8—N1—C7—C6	179.3 (2)	C11—C12—C13—C14	0.4 (5)
C5—C6—C7—O1	11.0 (4)	C10—C9—C14—C13	1.7 (4)
C1—C6—C7—O1	−167.4 (3)	N2—C9—C14—C13	178.5 (2)
C5—C6—C7—N1	−169.4 (2)	C12—C13—C14—C9	−1.6 (4)
C1—C6—C7—N1	12.2 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.86	1.93	2.638 (3)	138
C14—H14···S1	0.93	2.80	3.209 (3)	107
C1—H1A···S1^i	0.93	2.78	3.666 (3)	159

Symmetry code: (i) −x+1/2, y−1/2, −z+1/2.