1-Benzoyl-3-(4-hy-droxy-phen-yl)thio-urea.

In the title compound, C(14)H(12)N(2)O(2)S, the amino-phenol and the benzoyl groups adopt a syn-anti configuration with respect to the thiono C=S group across the thio-urea C-N. The dihedral angle between the mean planes of the benzoyl and hy-droxy-phenyl rings is 36.77 (8)°. The mol-ecules are stabilized by intra-molecular N-H⋯O hydrogen bonds. In the crystal, weak inter-molecular C-H⋯O, O-H⋯S and N-H⋯O hydrogen bonds link the mol-ecules into a chain along the c axis.

Related literature

For the preparation and chemical properties of related compounds, see: Zhang et al. (2001 ▶). For related structures, see: Abosadiya et al. (2007 ▶); Hung et al. (2010 ▶); Yamin & Yusof (2003 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C14H12N2O2S

M = 272.33

Orthorhombic,

a = 5.5865 (10) Å

b = 14.451 (2) Å

c = 16.462 (3) Å

V = 1329.0 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 298 K

0.50 × 0.48 × 0.35 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.886, T max = 0.919

7608 measured reflections

2351 independent reflections

2143 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.085

S = 1.05

2351 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.14 e Å−3

Absolute structure: Flack (1983 ▶), 958 Friedel pairs

Flack parameter: 0.09 (9)

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810045988/jj2068sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810045988/jj2068Isup2.hkl

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

C14H12N2O2S	F(000) = 568
Mr = 272.33	Dx = 1.361 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1024 reflections
a = 5.5865 (10) Å	θ = 1.9–25.0°
b = 14.451 (2) Å	µ = 0.24 mm−1
c = 16.462 (3) Å	T = 298 K
V = 1329.0 (4) Å3	Block, brown
Z = 4	0.50 × 0.48 × 0.35 mm

Bruker SMART APEX CCD area-detector diffractometer	2351 independent reflections
Radiation source: fine-focus sealed tube	2143 reflections with I > 2σ(I)
graphite	Rint = 0.018
ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −6→6
Tmin = 0.886, Tmax = 0.919	k = −15→17
7608 measured reflections	l = −19→17

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)] = 0.031	H-atom parameters constrained
wR(F2) = 0.085	w = 1/[σ2(Fo2) + (0.0494P)2 + 0.1346P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
2351 reflections	Δρmax = 0.13 e Å−3
173 parameters	Δρmin = −0.14 e Å−3
0 restraints	Absolute structure: Flack (1983), 958 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.09 (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.

	x	y	z	Uiso*/Ueq
S1	1.13932 (14)	−0.04354 (4)	0.71251 (4)	0.0812 (2)
O1	0.7785 (3)	0.23667 (10)	0.72476 (9)	0.0719 (4)
N1	0.8692 (3)	0.09206 (10)	0.76731 (8)	0.0518 (4)
H1B	0.8429	0.0530	0.8057	0.062*
N2	1.0996 (3)	0.12902 (11)	0.65596 (9)	0.0565 (4)
H2B	1.0469	0.1841	0.6646	0.068*
C1	0.5090 (4)	0.10914 (14)	0.89160 (13)	0.0632 (5)
H1A	0.6077	0.0573	0.8928	0.076*
C2	0.3268 (5)	0.11715 (16)	0.94751 (14)	0.0712 (6)
H2A	0.3032	0.0712	0.9862	0.085*
C3	0.1812 (4)	0.19276 (18)	0.94584 (14)	0.0726 (6)
H3A	0.0581	0.1983	0.9836	0.087*
C4	0.2149 (4)	0.26068 (17)	0.88890 (14)	0.0734 (6)
H4A	0.1140	0.3119	0.8879	0.088*
C5	0.3978 (4)	0.25336 (14)	0.83317 (12)	0.0632 (5)
H5A	0.4208	0.3000	0.7950	0.076*
C6	0.5475 (3)	0.17701 (12)	0.83367 (10)	0.0487 (4)
C7	0.7395 (4)	0.17240 (12)	0.77127 (10)	0.0512 (4)
C8	1.0373 (4)	0.06508 (13)	0.70994 (11)	0.0527 (4)
C9	1.2439 (4)	0.11670 (13)	0.58521 (11)	0.0504 (4)
C10	1.1577 (4)	0.15191 (12)	0.51275 (11)	0.0520 (5)
H10A	1.0118	0.1829	0.5119	0.062*
C11	1.2858 (4)	0.14146 (12)	0.44198 (11)	0.0518 (5)
H11A	1.2257	0.1643	0.3933	0.062*
C12	1.5042 (3)	0.09692 (12)	0.44377 (12)	0.0515 (5)
C13	1.5928 (4)	0.06247 (16)	0.51603 (11)	0.0596 (5)
H13A	1.7399	0.0323	0.5170	0.072*
C14	1.4626 (4)	0.07290 (16)	0.58682 (12)	0.0594 (5)
H14A	1.5229	0.0503	0.6356	0.071*
O2	1.6406 (3)	0.08472 (10)	0.37487 (9)	0.0682 (4)
H2C	1.5717	0.1079	0.3359	0.102*

	U11	U22	U33	U12	U13	U23
S1	0.1110 (5)	0.0497 (3)	0.0828 (4)	0.0182 (3)	0.0277 (4)	0.0010 (3)
O1	0.1018 (11)	0.0536 (8)	0.0603 (8)	0.0184 (8)	0.0223 (8)	0.0179 (6)
N1	0.0712 (10)	0.0432 (8)	0.0410 (7)	0.0061 (8)	0.0053 (7)	0.0030 (6)
N2	0.0712 (10)	0.0480 (8)	0.0504 (8)	0.0014 (8)	0.0101 (8)	−0.0027 (7)
C1	0.0732 (14)	0.0513 (11)	0.0649 (12)	0.0051 (10)	0.0142 (10)	0.0055 (9)
C2	0.0783 (15)	0.0630 (13)	0.0723 (13)	−0.0108 (12)	0.0191 (12)	0.0028 (11)
C3	0.0575 (13)	0.0890 (17)	0.0713 (13)	−0.0058 (12)	0.0105 (11)	−0.0166 (13)
C4	0.0649 (14)	0.0824 (16)	0.0728 (14)	0.0219 (12)	0.0005 (12)	−0.0090 (12)
C5	0.0755 (14)	0.0596 (12)	0.0546 (11)	0.0119 (11)	−0.0026 (11)	0.0023 (9)
C6	0.0573 (11)	0.0472 (10)	0.0416 (8)	0.0009 (8)	−0.0045 (8)	−0.0040 (7)
C7	0.0669 (11)	0.0461 (10)	0.0406 (9)	0.0026 (9)	−0.0032 (8)	0.0018 (7)
C8	0.0627 (11)	0.0508 (10)	0.0446 (9)	−0.0008 (8)	−0.0022 (8)	−0.0056 (8)
C9	0.0560 (11)	0.0481 (9)	0.0471 (9)	−0.0079 (9)	0.0045 (8)	−0.0071 (8)
C10	0.0548 (11)	0.0411 (9)	0.0600 (11)	0.0009 (9)	0.0083 (9)	0.0050 (8)
C11	0.0618 (12)	0.0426 (10)	0.0509 (10)	−0.0032 (8)	0.0049 (9)	0.0051 (8)
C12	0.0543 (11)	0.0470 (10)	0.0531 (10)	−0.0119 (9)	0.0061 (8)	−0.0105 (8)
C13	0.0464 (10)	0.0724 (13)	0.0602 (11)	−0.0001 (10)	−0.0044 (9)	−0.0115 (10)
C14	0.0522 (11)	0.0780 (13)	0.0480 (10)	−0.0026 (10)	−0.0083 (8)	−0.0081 (9)
O2	0.0727 (10)	0.0735 (9)	0.0583 (8)	0.0002 (8)	0.0169 (7)	−0.0080 (7)

S1—C8	1.670 (2)	C4—H4A	0.9300
O1—C7	1.223 (2)	C5—C6	1.385 (3)
N1—C7	1.370 (2)	C5—H5A	0.9300
N1—C8	1.388 (2)	C6—C7	1.486 (3)
N1—H1B	0.8600	C9—C14	1.376 (3)
N2—C8	1.328 (2)	C9—C10	1.384 (3)
N2—C9	1.428 (2)	C10—C11	1.376 (3)
N2—H2B	0.8600	C10—H10A	0.9300
C1—C2	1.377 (3)	C11—C12	1.379 (3)
C1—C6	1.385 (3)	C11—H11A	0.9300
C1—H1A	0.9300	C12—O2	1.378 (2)
C2—C3	1.362 (3)	C12—C13	1.381 (3)
C2—H2A	0.9300	C13—C14	1.382 (3)
C3—C4	1.370 (3)	C13—H13A	0.9300
C3—H3A	0.9300	C14—H14A	0.9300
C4—C5	1.377 (3)	O2—H2C	0.8200
C7—N1—C8	128.94 (15)	O1—C7—C6	121.81 (17)
C7—N1—H1B	115.5	N1—C7—C6	116.91 (15)
C8—N1—H1B	115.5	N2—C8—N1	115.91 (16)
C8—N2—C9	127.36 (16)	N2—C8—S1	125.54 (15)
C8—N2—H2B	116.3	N1—C8—S1	118.53 (13)
C9—N2—H2B	116.3	C14—C9—C10	119.66 (17)
C2—C1—C6	121.0 (2)	C14—C9—N2	122.90 (17)
C2—C1—H1A	119.5	C10—C9—N2	117.43 (17)
C6—C1—H1A	119.5	C11—C10—C9	120.56 (18)
C3—C2—C1	119.7 (2)	C11—C10—H10A	119.7
C3—C2—H2A	120.2	C9—C10—H10A	119.7
C1—C2—H2A	120.2	C10—C11—C12	119.57 (18)
C2—C3—C4	120.4 (2)	C10—C11—H11A	120.2
C2—C3—H3A	119.8	C12—C11—H11A	120.2
C4—C3—H3A	119.8	O2—C12—C11	122.08 (18)
C3—C4—C5	120.2 (2)	O2—C12—C13	117.68 (18)
C3—C4—H4A	119.9	C11—C12—C13	120.24 (18)
C5—C4—H4A	119.9	C12—C13—C14	119.87 (19)
C4—C5—C6	120.4 (2)	C12—C13—H13A	120.1
C4—C5—H5A	119.8	C14—C13—H13A	120.1
C6—C5—H5A	119.8	C9—C14—C13	120.08 (19)
C1—C6—C5	118.32 (18)	C9—C14—H14A	120.0
C1—C6—C7	123.80 (17)	C13—C14—H14A	120.0
C5—C6—C7	117.87 (17)	C12—O2—H2C	109.5
O1—C7—N1	121.28 (18)
C6—C1—C2—C3	0.2 (3)	C9—N2—C8—S1	7.0 (3)
C1—C2—C3—C4	0.1 (4)	C7—N1—C8—N2	7.5 (3)
C2—C3—C4—C5	−0.5 (4)	C7—N1—C8—S1	−171.15 (16)
C3—C4—C5—C6	0.6 (3)	C8—N2—C9—C14	−49.9 (3)
C2—C1—C6—C5	−0.1 (3)	C8—N2—C9—C10	130.9 (2)
C2—C1—C6—C7	−179.5 (2)	C14—C9—C10—C11	1.6 (3)
C4—C5—C6—C1	−0.3 (3)	N2—C9—C10—C11	−179.13 (16)
C4—C5—C6—C7	179.15 (19)	C9—C10—C11—C12	−1.2 (3)
C8—N1—C7—O1	−7.2 (3)	C10—C11—C12—O2	−179.80 (17)
C8—N1—C7—C6	171.87 (17)	C10—C11—C12—C13	0.4 (3)
C1—C6—C7—O1	−174.8 (2)	O2—C12—C13—C14	−179.95 (18)
C5—C6—C7—O1	5.8 (3)	C11—C12—C13—C14	−0.2 (3)
C1—C6—C7—N1	6.1 (3)	C10—C9—C14—C13	−1.4 (3)
C5—C6—C7—N1	−173.29 (17)	N2—C9—C14—C13	179.44 (19)
C9—N2—C8—N1	−171.58 (17)	C12—C13—C14—C9	0.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O1	0.86	1.95	2.631 (2)	135
N1—H1B···O2i	0.86	2.29	3.109 (2)	158
O2—H2C···S1ii	0.82	2.53	3.1533 (18)	134
C1—H1A···O2i	0.93	2.51	3.429 (3)	172
C11—H11A···O1iii	0.93	2.43	3.262 (2)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯O1	0.86	1.95	2.631 (2)	135
N1—H1B⋯O2i	0.86	2.29	3.109 (2)	158
O2—H2C⋯S1ii	0.82	2.53	3.1533 (18)	134
C1—H1A⋯O2i	0.93	2.51	3.429 (3)	172
C11—H11A⋯O1iii	0.93	2.43	3.262 (2)	149

Symmetry codes: (i) ; (ii) ; (iii) .