3-{(E)-[1-(2-Hy-droxy-phen-yl)ethyl-idene]amino}-1-(2-methyl-phen-yl)thio-urea.

In the title thio-urea derivative, C(16)H(17)N(3)OS, the hy-droxy- and methyl-substituted benzene rings form dihedral angles of 9.62 (12) and 55.69 (6)°, respectively, with the central CN(3)S chromophore (r.m.s. deviation = 0.0117 Å). An intra-molecular O-H⋯N hydrogen bond ensures the coplanarity of the central atoms. The H atoms of the NH groups are syn and the conformation about the N=C double bond [1.295 (4) Å] is E. In the crystal, helical supra-molecular chains sustained primarily by N-H⋯S hydrogen bonds are found. Additional stabilization is provided by C-H⋯π and π-π [ring centroid(hy-droxy-benzene)⋯ring centroid(methyl-benzene) = 3.8524 (18) Å] inter-actions.

Related literature

For pharmaceutical applications of thio­ruea derivatives, see: Venkatachalam et al. (2004 ▶); Bruce et al. (2007 ▶). For related thio­urea structures, see: Normaya et al. (2011 ▶); Salam et al. (2011 ▶); Dzulkifli et al. (2011 ▶).

Experimental

Crystal data

C16H17N3OS

M = 299.39

Monoclinic,

a = 14.6966 (8) Å

b = 7.3586 (4) Å

c = 14.0926 (8) Å

β = 94.358 (5)°

V = 1519.66 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 100 K

0.30 × 0.10 × 0.05 mm

Data collection

Agilent Supernova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.419, T max = 1.000

7614 measured reflections

3375 independent reflections

2094 reflections with I > 2σ(I)

R int = 0.066

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.174

S = 1.00

3375 reflections

201 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.34 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811013729/hg5025sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811013729/hg5025Isup2.hkl

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

C16H17N3OS	F(000) = 632
Mr = 299.39	Dx = 1.309 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1905 reflections
a = 14.6966 (8) Å	θ = 2.8–29.3°
b = 7.3586 (4) Å	µ = 0.22 mm−1
c = 14.0926 (8) Å	T = 100 K
β = 94.358 (5)°	Prism, light-yellow
V = 1519.66 (15) Å3	0.30 × 0.10 × 0.05 mm
Z = 4

Agilent Supernova Dual diffractometer with an Atlas detector	3375 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2094 reflections with I > 2σ(I)
Mirror	Rint = 0.066
Detector resolution: 10.4041 pixels mm-1	θmax = 27.5°, θmin = 2.8°
ω scans	h = −14→19
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −9→7
Tmin = 0.419, Tmax = 1.000	l = −18→15
7614 measured reflections

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.174	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0769P)2] where P = (Fo2 + 2Fc2)/3
3375 reflections	(Δ/σ)max < 0.001
201 parameters	Δρmax = 0.34 e Å−3
3 restraints	Δρmin = −0.34 e Å−3

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
S1	0.46230 (5)	0.24817 (10)	0.38597 (5)	0.0188 (2)
O1	0.21619 (14)	0.2307 (3)	0.31997 (15)	0.0250 (5)
H1O	0.2693 (11)	0.261 (4)	0.308 (2)	0.038*
N1	0.33770 (15)	0.3710 (3)	0.22261 (17)	0.0182 (6)
N2	0.42781 (16)	0.4196 (3)	0.21980 (18)	0.0190 (6)
H2N	0.4433 (19)	0.497 (3)	0.1764 (16)	0.023*
N3	0.57409 (16)	0.4362 (3)	0.27942 (17)	0.0197 (6)
H3N	0.5801 (19)	0.496 (4)	0.2259 (13)	0.024*
C1	0.1592 (2)	0.2588 (4)	0.2410 (2)	0.0229 (7)
C2	0.0685 (2)	0.2066 (5)	0.2458 (3)	0.0309 (8)
H2	0.0496	0.1544	0.3027	0.037*
C3	0.0062 (2)	0.2298 (5)	0.1692 (3)	0.0331 (9)
H3A	−0.0553	0.1927	0.1732	0.040*
C4	0.0327 (2)	0.3073 (5)	0.0857 (3)	0.0320 (8)
H4	−0.0104	0.3236	0.0327	0.038*
C5	0.1220 (2)	0.3603 (4)	0.0806 (2)	0.0260 (8)
H5A	0.1396	0.4142	0.0236	0.031*
C6	0.18777 (19)	0.3372 (4)	0.1568 (2)	0.0200 (7)
C7	0.28345 (19)	0.3879 (4)	0.1464 (2)	0.0189 (7)
C8	0.3131 (2)	0.4548 (4)	0.0530 (2)	0.0229 (7)
H8A	0.3795	0.4432	0.0525	0.034*
H8B	0.2957	0.5827	0.0445	0.034*
H8C	0.2834	0.3824	0.0012	0.034*
C9	0.48965 (19)	0.3751 (4)	0.2920 (2)	0.0174 (7)
C10	0.65424 (19)	0.4166 (4)	0.3422 (2)	0.0172 (7)
C11	0.6563 (2)	0.4776 (4)	0.4351 (2)	0.0201 (7)
H11	0.6024	0.5242	0.4592	0.024*
C12	0.7355 (2)	0.4712 (4)	0.4928 (2)	0.0252 (7)
H12A	0.7364	0.5112	0.5570	0.030*
C13	0.8147 (2)	0.4057 (4)	0.4568 (2)	0.0253 (7)
H13	0.8703	0.4035	0.4960	0.030*
C14	0.8128 (2)	0.3441 (4)	0.3647 (2)	0.0231 (7)
H14	0.8671	0.2974	0.3414	0.028*
C15	0.73287 (19)	0.3485 (4)	0.3047 (2)	0.0195 (7)
C16	0.7318 (2)	0.2841 (4)	0.2034 (2)	0.0260 (8)
H16A	0.7815	0.1969	0.1974	0.039*
H16B	0.7401	0.3882	0.1615	0.039*
H16C	0.6733	0.2253	0.1851	0.039*

	U11	U22	U33	U12	U13	U23
S1	0.0225 (4)	0.0163 (4)	0.0179 (4)	−0.0009 (3)	0.0039 (3)	−0.0001 (3)
O1	0.0214 (11)	0.0291 (13)	0.0247 (13)	−0.0029 (10)	0.0027 (10)	−0.0005 (10)
N1	0.0150 (12)	0.0148 (13)	0.0247 (15)	−0.0010 (10)	0.0019 (10)	−0.0010 (11)
N2	0.0179 (13)	0.0166 (14)	0.0222 (15)	−0.0023 (10)	0.0002 (11)	0.0044 (11)
N3	0.0187 (13)	0.0205 (14)	0.0199 (15)	−0.0006 (11)	0.0016 (11)	0.0052 (11)
C1	0.0245 (16)	0.0172 (16)	0.0269 (18)	0.0046 (13)	0.0018 (13)	−0.0085 (14)
C2	0.0234 (17)	0.030 (2)	0.040 (2)	−0.0028 (14)	0.0098 (15)	−0.0020 (16)
C3	0.0198 (17)	0.031 (2)	0.049 (2)	−0.0018 (14)	0.0039 (16)	−0.0077 (17)
C4	0.0248 (18)	0.0298 (19)	0.040 (2)	0.0018 (15)	−0.0039 (15)	0.0006 (17)
C5	0.0242 (17)	0.0207 (17)	0.032 (2)	0.0010 (14)	−0.0026 (14)	−0.0014 (15)
C6	0.0174 (15)	0.0158 (16)	0.0266 (18)	−0.0010 (12)	0.0003 (13)	−0.0037 (13)
C7	0.0209 (15)	0.0104 (15)	0.0250 (18)	0.0038 (12)	0.0004 (13)	−0.0030 (13)
C8	0.0248 (16)	0.0192 (17)	0.0247 (18)	−0.0002 (13)	0.0021 (13)	−0.0036 (14)
C9	0.0180 (15)	0.0151 (15)	0.0197 (16)	0.0034 (12)	0.0045 (12)	−0.0028 (13)
C10	0.0185 (15)	0.0126 (15)	0.0205 (17)	−0.0006 (12)	0.0014 (12)	0.0014 (12)
C11	0.0272 (16)	0.0095 (14)	0.0239 (18)	0.0015 (13)	0.0045 (13)	−0.0009 (13)
C12	0.0354 (19)	0.0158 (16)	0.0235 (18)	−0.0033 (14)	−0.0037 (14)	0.0013 (14)
C13	0.0249 (17)	0.0192 (17)	0.030 (2)	−0.0021 (13)	−0.0091 (14)	0.0055 (14)
C14	0.0171 (15)	0.0183 (16)	0.034 (2)	0.0001 (13)	0.0034 (13)	0.0026 (15)
C15	0.0262 (16)	0.0132 (15)	0.0200 (17)	−0.0058 (13)	0.0063 (13)	−0.0003 (13)
C16	0.0275 (17)	0.0240 (18)	0.0276 (19)	−0.0018 (14)	0.0094 (14)	−0.0020 (14)

S1—C9	1.694 (3)	C6—C7	1.473 (4)
O1—C1	1.357 (4)	C7—C8	1.500 (4)
O1—H1O	0.842 (10)	C8—H8A	0.9800
N1—C7	1.295 (4)	C8—H8B	0.9800
N1—N2	1.375 (3)	C8—H8C	0.9800
N2—C9	1.352 (4)	C10—C11	1.383 (4)
N2—H2N	0.880 (10)	C10—C15	1.400 (4)
N3—C9	1.344 (3)	C11—C12	1.369 (4)
N3—C10	1.426 (4)	C11—H11	0.9500
N3—H3N	0.882 (10)	C12—C13	1.391 (4)
C1—C2	1.394 (4)	C12—H12A	0.9500
C1—C6	1.411 (4)	C13—C14	1.373 (4)
C2—C3	1.372 (5)	C13—H13	0.9500
C2—H2	0.9500	C14—C15	1.395 (4)
C3—C4	1.390 (5)	C14—H14	0.9500
C3—H3A	0.9500	C15—C16	1.503 (4)
C4—C5	1.376 (4)	C16—H16A	0.9800
C4—H4	0.9500	C16—H16B	0.9800
C5—C6	1.400 (4)	C16—H16C	0.9800
C5—H5A	0.9500
C1—O1—H1O	108 (2)	H8A—C8—H8B	109.5
C7—N1—N2	119.0 (2)	C7—C8—H8C	109.5
C9—N2—N1	120.6 (2)	H8A—C8—H8C	109.5
C9—N2—H2N	119 (2)	H8B—C8—H8C	109.5
N1—N2—H2N	119.3 (19)	N3—C9—N2	113.2 (2)
C9—N3—C10	127.7 (2)	N3—C9—S1	124.3 (2)
C9—N3—H3N	115.6 (19)	N2—C9—S1	122.4 (2)
C10—N3—H3N	116.7 (19)	C11—C10—C15	121.0 (3)
O1—C1—C2	116.8 (3)	C11—C10—N3	120.9 (3)
O1—C1—C6	123.2 (3)	C15—C10—N3	117.9 (3)
C2—C1—C6	120.0 (3)	C12—C11—C10	120.5 (3)
C3—C2—C1	120.8 (3)	C12—C11—H11	119.7
C3—C2—H2	119.6	C10—C11—H11	119.7
C1—C2—H2	119.6	C11—C12—C13	119.5 (3)
C2—C3—C4	120.2 (3)	C11—C12—H12A	120.2
C2—C3—H3A	119.9	C13—C12—H12A	120.2
C4—C3—H3A	119.9	C14—C13—C12	120.1 (3)
C5—C4—C3	119.4 (3)	C14—C13—H13	120.0
C5—C4—H4	120.3	C12—C13—H13	120.0
C3—C4—H4	120.3	C13—C14—C15	121.5 (3)
C4—C5—C6	122.1 (3)	C13—C14—H14	119.3
C4—C5—H5A	119.0	C15—C14—H14	119.3
C6—C5—H5A	119.0	C14—C15—C10	117.4 (3)
C5—C6—C1	117.6 (3)	C14—C15—C16	121.1 (3)
C5—C6—C7	120.1 (3)	C10—C15—C16	121.5 (3)
C1—C6—C7	122.3 (3)	C15—C16—H16A	109.5
N1—C7—C6	115.1 (3)	C15—C16—H16B	109.5
N1—C7—C8	123.9 (3)	H16A—C16—H16B	109.5
C6—C7—C8	120.9 (3)	C15—C16—H16C	109.5
C7—C8—H8A	109.5	H16A—C16—H16C	109.5
C7—C8—H8B	109.5	H16B—C16—H16C	109.5
C7—N1—N2—C9	−168.5 (3)	C10—N3—C9—N2	178.6 (3)
O1—C1—C2—C3	−179.9 (3)	C10—N3—C9—S1	−3.6 (4)
C6—C1—C2—C3	0.3 (5)	N1—N2—C9—N3	−178.5 (2)
C1—C2—C3—C4	−0.5 (5)	N1—N2—C9—S1	3.7 (4)
C2—C3—C4—C5	0.1 (5)	C9—N3—C10—C11	−56.4 (4)
C3—C4—C5—C6	0.6 (5)	C9—N3—C10—C15	129.0 (3)
C4—C5—C6—C1	−0.8 (5)	C15—C10—C11—C12	−0.5 (4)
C4—C5—C6—C7	177.0 (3)	N3—C10—C11—C12	−174.9 (3)
O1—C1—C6—C5	−179.4 (3)	C10—C11—C12—C13	1.1 (4)
C2—C1—C6—C5	0.3 (4)	C11—C12—C13—C14	−1.5 (5)
O1—C1—C6—C7	2.8 (5)	C12—C13—C14—C15	1.2 (5)
C2—C1—C6—C7	−177.4 (3)	C13—C14—C15—C10	−0.6 (4)
N2—N1—C7—C6	−178.4 (2)	C13—C14—C15—C16	178.8 (3)
N2—N1—C7—C8	1.2 (4)	C11—C10—C15—C14	0.2 (4)
C5—C6—C7—N1	176.2 (3)	N3—C10—C15—C14	174.8 (3)
C1—C6—C7—N1	−6.1 (4)	C11—C10—C15—C16	−179.2 (3)
C5—C6—C7—C8	−3.4 (4)	N3—C10—C15—C16	−4.6 (4)
C1—C6—C7—C8	174.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···N1	0.842 (10)	1.81 (2)	2.551 (3)	145 (3)
N2—H2n···S1i	0.880 (10)	2.508 (16)	3.323 (2)	154 (3)
N3—H3n···S1i	0.882 (10)	2.485 (17)	3.286 (3)	151 (2)
C8—H8b···Cg1i	0.98	2.59	3.501 (3)	155

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C10–C15 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯N1	0.84 (1)	1.81 (2)	2.551 (3)	145 (3)
N2—H2n⋯S1i	0.88 (1)	2.51 (2)	3.323 (2)	154 (3)
N3—H3n⋯S1i	0.88 (1)	2.49 (2)	3.286 (3)	151 (2)
C8—H8b⋯Cg1i	0.98	2.59	3.501 (3)	155

Symmetry code: (i) .