3-Benzoyl-1-[4-(methyl-sulfan-yl)phen-yl]thio-urea.

The title compound, C15H14N2OS2, adopts a helix conformation. An intra-molecular N-H⋯O hydrogen bond leads to a six-membered pseudo-ring [r.m.s. deviation = 0.0212 Å, maximum deviation = 0.033 (1) Å for the N atom bearing the benzoyl group] in the central unit. The benzene and (methyl-sulfan-yl)benzene ring [r.m.s = 0.0028 Å and largest deviation of 0.067 (3) Å for the methyl-sulfanyl C atom] make dihedral angles of 31.76 (8) and 54.68 (6)°, respectively, with the pseudo-ring plane. The dihedral angle between the benzene rings is 85.71 (8)°. In the crystal, pairs of weak N-H⋯S inter-actions form inversion dimers and mediate a linear chain along [001].

Related literature

For related compounds found in CSD (Allen, 2002 ▶) see: Al-abbasi et al. (2010 ▶); Cao et al. (1996 ▶). For the structure of the unsubstituted compound, see: Yamin & Yusof (2003 ▶). For details of the synthesis, see: Zhang et al. (2001 ▶).

Experimental

Crystal data

C15H14N2OS2

M = 302.42

Triclinic,

a = 5.9131 (2) Å

b = 9.5826 (3) Å

c = 13.3149 (4) Å

α = 96.729 (1)°

β = 91.533 (1)°

γ = 94.503 (1)°

V = 746.46 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.35 mm−1

T = 308 K

0.7 × 0.34 × 0.24 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2010 ▶) T min = 0.917, T max = 1.0

11518 measured reflections

3285 independent reflections

2908 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.099

S = 1

3285 reflections

183 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813013159/qm2097sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813013159/qm2097Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813013159/qm2097Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C15H14N2OS2	Z = 2
Mr = 302.42	F(000) = 316
Triclinic, P1	Dx = 1.345 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.9131 (2) Å	Cell parameters from 7480 reflections
b = 9.5826 (3) Å	θ = 5.0–54.1°
c = 13.3149 (4) Å	µ = 0.35 mm−1
α = 96.729 (1)°	T = 308 K
β = 91.533 (1)°	Prism, colourless
γ = 94.503 (1)°	0.7 × 0.34 × 0.24 mm
V = 746.46 (4) Å3

Bruker APEXII CCD diffractometer	2908 reflections with I > 2σ(I)
Multilayer optics monochromator	Rint = 0.021
φ and ω scans	θmax = 27.1°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2010)	h = −7→7
Tmin = 0.917, Tmax = 1.0	k = −12→11
11518 measured reflections	l = −17→17
3285 independent reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034	H-atom parameters constrained
wR(F2) = 0.099	w = 1/[σ2(Fo2) + (0.0481P)2 + 0.2312P] where P = (Fo2 + 2Fc2)/3
S = 1	(Δ/σ)max = 0.029
3285 reflections	Δρmax = 0.19 e Å−3
183 parameters	Δρmin = −0.22 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.038 (4)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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.

	x	y	z	Uiso*/Ueq
N2	0.6544 (2)	0.96378 (13)	0.72447 (9)	0.0477 (3)
H2	0.6015	0.8875	0.6881	0.057*
S1	0.66478 (9)	1.12397 (4)	0.90198 (3)	0.06291 (17)
C7	−0.0806 (4)	0.4643 (2)	0.83445 (17)	0.0745 (6)
H7	−0.1007	0.368	0.8133	0.089*
C4	−0.0192 (3)	0.75005 (17)	0.89870 (12)	0.0506 (3)
H4	0.0007	0.8462	0.9205	0.061*
C11	0.9002 (3)	1.18452 (18)	0.53854 (11)	0.0519 (4)
H11	0.8552	1.2143	0.4776	0.062*
C1	0.5795 (2)	0.98624 (14)	0.81784 (10)	0.0418 (3)
C2	0.3113 (3)	0.77171 (15)	0.78408 (11)	0.0460 (3)
C5	−0.1955 (3)	0.6678 (2)	0.93446 (15)	0.0647 (5)
H5	−0.2941	0.7087	0.9803	0.078*
C12	1.1161 (2)	1.22405 (16)	0.57927 (11)	0.0453 (3)
C13	1.1798 (3)	1.17840 (18)	0.67070 (12)	0.0518 (4)
H13	1.3244	1.2054	0.699	0.062*
N1	0.4143 (2)	0.88724 (12)	0.84430 (9)	0.0433 (3)
H1	0.3711	0.8995	0.9056	0.052*
O1	0.3658 (2)	0.73896 (13)	0.69735 (9)	0.0679 (4)
C10	0.7507 (3)	1.10043 (17)	0.58862 (11)	0.0509 (4)
H10	0.6051	1.0746	0.5611	0.061*
C3	0.1268 (2)	0.68897 (15)	0.83058 (11)	0.0445 (3)
C14	1.0303 (3)	1.09336 (18)	0.71986 (12)	0.0504 (4)
H14	1.0751	1.0624	0.7804	0.061*
C9	0.8147 (2)	1.05463 (14)	0.67869 (10)	0.0428 (3)
S2	1.32148 (7)	1.32969 (6)	0.52237 (4)	0.06877 (17)
C8	0.0945 (3)	0.54539 (17)	0.79760 (14)	0.0604 (4)
H8	0.1906	0.5041	0.7508	0.072*
C6	−0.2246 (3)	0.5255 (2)	0.90207 (17)	0.0748 (6)
H6	−0.343	0.4706	0.9263	0.09*
C15	1.1792 (3)	1.3752 (2)	0.41292 (15)	0.0684 (5)
H15A	1.1327	1.2911	0.3684	0.103*
H15B	1.2801	1.4357	0.3787	0.103*
H15C	1.0482	1.4235	0.4326	0.103*

	U11	U22	U33	U12	U13	U23
N2	0.0555 (7)	0.0429 (6)	0.0431 (6)	−0.0071 (5)	0.0160 (5)	0.0024 (5)
S1	0.0905 (3)	0.0470 (2)	0.0462 (2)	−0.0230 (2)	0.0246 (2)	−0.00146 (16)
C7	0.0898 (14)	0.0473 (9)	0.0854 (14)	−0.0157 (9)	0.0241 (11)	0.0132 (9)
C4	0.0487 (8)	0.0492 (8)	0.0547 (9)	0.0025 (6)	0.0078 (6)	0.0100 (7)
C11	0.0503 (8)	0.0663 (10)	0.0393 (7)	−0.0055 (7)	0.0054 (6)	0.0138 (7)
C1	0.0477 (7)	0.0374 (7)	0.0416 (7)	0.0016 (5)	0.0110 (6)	0.0095 (5)
C2	0.0521 (8)	0.0418 (7)	0.0440 (7)	−0.0021 (6)	0.0100 (6)	0.0065 (6)
C5	0.0528 (9)	0.0740 (11)	0.0698 (11)	0.0033 (8)	0.0211 (8)	0.0161 (9)
C12	0.0423 (7)	0.0493 (8)	0.0451 (7)	0.0007 (6)	0.0133 (6)	0.0085 (6)
C13	0.0373 (7)	0.0671 (10)	0.0525 (8)	0.0004 (6)	0.0061 (6)	0.0148 (7)
N1	0.0512 (7)	0.0402 (6)	0.0384 (6)	−0.0042 (5)	0.0125 (5)	0.0070 (5)
O1	0.0822 (9)	0.0649 (7)	0.0496 (7)	−0.0246 (6)	0.0248 (6)	−0.0069 (5)
C10	0.0470 (8)	0.0623 (9)	0.0406 (7)	−0.0116 (7)	0.0048 (6)	0.0043 (6)
C3	0.0480 (8)	0.0426 (7)	0.0433 (7)	−0.0032 (6)	0.0057 (6)	0.0107 (6)
C14	0.0465 (8)	0.0622 (9)	0.0463 (8)	0.0070 (7)	0.0092 (6)	0.0187 (7)
C9	0.0471 (7)	0.0409 (7)	0.0403 (7)	0.0000 (6)	0.0151 (6)	0.0041 (5)
S2	0.0501 (3)	0.0899 (4)	0.0694 (3)	−0.0149 (2)	0.0089 (2)	0.0348 (3)
C8	0.0725 (11)	0.0450 (8)	0.0630 (10)	−0.0055 (7)	0.0204 (8)	0.0063 (7)
C6	0.0698 (12)	0.0687 (12)	0.0873 (14)	−0.0163 (9)	0.0230 (10)	0.0250 (10)
C15	0.0701 (11)	0.0769 (12)	0.0640 (11)	0.0050 (9)	0.0201 (9)	0.0291 (9)

N2—C1	1.3303 (18)	C5—H5	0.93
N2—C9	1.4331 (17)	C12—C13	1.393 (2)
N2—H2	0.86	C12—S2	1.7635 (14)
S1—C1	1.6643 (15)	C13—C14	1.384 (2)
C7—C6	1.370 (3)	C13—H13	0.93
C7—C8	1.380 (2)	N1—H1	0.86
C7—H7	0.93	C10—C9	1.378 (2)
C4—C3	1.381 (2)	C10—H10	0.93
C4—C5	1.386 (2)	C3—C8	1.391 (2)
C4—H4	0.93	C14—C9	1.380 (2)
C11—C12	1.380 (2)	C14—H14	0.93
C11—C10	1.386 (2)	S2—C15	1.778 (2)
C11—H11	0.93	C8—H8	0.93
C1—N1	1.3890 (17)	C6—H6	0.93
C2—O1	1.2193 (17)	C15—H15A	0.96
C2—N1	1.3783 (18)	C15—H15B	0.96
C2—C3	1.4891 (19)	C15—H15C	0.96
C5—C6	1.377 (3)
C1—N2—C9	126.20 (12)	C2—N1—H1	116.1
C1—N2—H2	116.9	C1—N1—H1	116.1
C9—N2—H2	116.9	C9—C10—C11	120.90 (14)
C6—C7—C8	120.07 (17)	C9—C10—H10	119.5
C6—C7—H7	120	C11—C10—H10	119.5
C8—C7—H7	120	C4—C3—C8	119.70 (14)
C3—C4—C5	119.86 (15)	C4—C3—C2	122.95 (13)
C3—C4—H4	120.1	C8—C3—C2	117.22 (13)
C5—C4—H4	120.1	C9—C14—C13	119.77 (14)
C12—C11—C10	119.89 (14)	C9—C14—H14	120.1
C12—C11—H11	120.1	C13—C14—H14	120.1
C10—C11—H11	120.1	C10—C9—C14	119.61 (13)
N2—C1—N1	116.19 (12)	C10—C9—N2	117.94 (13)
N2—C1—S1	124.91 (11)	C14—C9—N2	122.42 (13)
N1—C1—S1	118.88 (10)	C12—S2—C15	104.62 (8)
O1—C2—N1	122.34 (13)	C7—C8—C3	119.92 (16)
O1—C2—C3	121.47 (13)	C7—C8—H8	120
N1—C2—C3	116.18 (12)	C3—C8—H8	120
C6—C5—C4	119.95 (16)	C7—C6—C5	120.50 (16)
C6—C5—H5	120	C7—C6—H6	119.8
C4—C5—H5	120	C5—C6—H6	119.8
C11—C12—C13	119.09 (13)	S2—C15—H15A	109.5
C11—C12—S2	124.05 (12)	S2—C15—H15B	109.5
C13—C12—S2	116.87 (11)	H15A—C15—H15B	109.5
C14—C13—C12	120.74 (14)	S2—C15—H15C	109.5
C14—C13—H13	119.6	H15A—C15—H15C	109.5
C12—C13—H13	119.6	H15B—C15—H15C	109.5
C2—N1—C1	127.82 (12)
C9—N2—C1—N1	176.58 (13)	O1—C2—C3—C8	30.6 (2)
C9—N2—C1—S1	−2.0 (2)	N1—C2—C3—C8	−150.00 (15)
C3—C4—C5—C6	0.0 (3)	C12—C13—C14—C9	−0.8 (2)
C10—C11—C12—C13	−0.1 (2)	C11—C10—C9—C14	0.2 (2)
C10—C11—C12—S2	179.62 (12)	C11—C10—C9—N2	−177.77 (14)
C11—C12—C13—C14	0.7 (2)	C13—C14—C9—C10	0.4 (2)
S2—C12—C13—C14	−179.05 (12)	C13—C14—C9—N2	178.27 (13)
O1—C2—N1—C1	3.7 (3)	C1—N2—C9—C10	−124.24 (17)
C3—C2—N1—C1	−175.71 (13)	C1—N2—C9—C14	57.8 (2)
N2—C1—N1—C2	−3.1 (2)	C11—C12—S2—C15	3.27 (17)
S1—C1—N1—C2	175.56 (12)	C13—C12—S2—C15	−177.03 (13)
C12—C11—C10—C9	−0.4 (2)	C6—C7—C8—C3	1.1 (3)
C5—C4—C3—C8	0.6 (2)	C4—C3—C8—C7	−1.2 (3)
C5—C4—C3—C2	176.20 (15)	C2—C3—C8—C7	−177.03 (17)
O1—C2—C3—C4	−145.13 (17)	C8—C7—C6—C5	−0.5 (4)
N1—C2—C3—C4	34.3 (2)	C4—C5—C6—C7	−0.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.86	1.93	2.6250 (16)	137
N1—H1···S1i	0.86	2.61	3.4358 (12)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1	0.86	1.93	2.6250 (16)	137
N1—H1⋯S1i	0.86	2.61	3.4358 (12)	161

Symmetry code: (i) .