3-[2-Hy-droxy-3-(2,4,6-trimethyl-phen-yl)prop-yl]-3-methyl-1-phenyl-thio-urea.

In the title compound, C(20)H(26)N(2)OS, four non-H atoms of the thio-urea unit are approximately planar (r.m.s. deviation = 0.005 Å); the phenyl and benzene rings are twisted out of this plane by 28.55 (7) and 60.00 (7)°, respectively. An intra-molecular N-H⋯O hydrogen bond occurs. The hy-droxy group is hydrogen bonded to the double-bond S atom of an inversion-related mol-ecule, generating a hydrogen-bonded dimer in the crystal structure.

Related literature

The title compund was prepared by a reaction of 1-methyl­amino-3-(2,4,6-trimethyl­phen­yl)propan-2-ol and phenyl iso­thio­cyanate; for the structure of the reactant 1-methyl­amino-3-(2,4,6-trimethyl­phen­yl)propan-2-ol, see: Maharramov et al. (2011 ▶).

Experimental

Crystal data

C20H26N2OS

M = 342.49

Monoclinic,

a = 14.6313 (11) Å

b = 8.1579 (6) Å

c = 16.4455 (12) Å

β = 109.040 (1)°

V = 1855.6 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.18 mm−1

T = 100 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.947, T max = 0.964

10052 measured reflections

4160 independent reflections

3542 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.112

S = 1.04

4160 reflections

229 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.38 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811012736/xu5185sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811012736/xu5185Isup2.hkl

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

C20H26N2OS	F(000) = 736
Mr = 342.49	Dx = 1.226 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4968 reflections
a = 14.6313 (11) Å	θ = 2.6–29.2°
b = 8.1579 (6) Å	µ = 0.18 mm−1
c = 16.4455 (12) Å	T = 100 K
β = 109.040 (1)°	Prism, colorless
V = 1855.6 (2) Å3	0.30 × 0.20 × 0.20 mm
Z = 4

Bruker SMART APEX diffractometer	4160 independent reflections
Radiation source: fine-focus sealed tube	3542 reflections with I > 2σ(I)
graphite	Rint = 0.028
φ and ω scans	θmax = 27.5°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→18
Tmin = 0.947, Tmax = 0.964	k = −10→10
10052 measured reflections	l = −20→20

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0617P)2 + 0.4837P] where P = (Fo2 + 2Fc2)/3
4160 reflections	(Δ/σ)max = 0.001
229 parameters	Δρmax = 0.38 e Å−3
2 restraints	Δρmin = −0.24 e Å−3

	x	y	z	Uiso*/Ueq
S1	0.35275 (3)	0.49063 (4)	0.61941 (2)	0.02172 (11)
O1	0.61082 (7)	0.26588 (12)	0.52099 (7)	0.0223 (2)
H1	0.6434 (13)	0.330 (2)	0.5027 (12)	0.041 (6)*
N1	0.51088 (8)	0.30365 (14)	0.65553 (7)	0.0197 (3)
N2	0.42327 (8)	0.31882 (14)	0.51317 (8)	0.0196 (2)
H2	0.4785 (9)	0.292 (2)	0.5069 (12)	0.032 (5)*
C1	0.81508 (10)	0.13935 (16)	0.59751 (10)	0.0216 (3)
C2	0.89199 (11)	0.21843 (18)	0.65953 (10)	0.0260 (3)
C3	0.97052 (11)	0.2735 (2)	0.63719 (12)	0.0320 (4)
H3	1.0215	0.3293	0.6790	0.038*
C4	0.97654 (12)	0.2495 (2)	0.55560 (12)	0.0340 (4)
C5	0.90094 (12)	0.1692 (2)	0.49568 (11)	0.0319 (4)
H5	0.9043	0.1508	0.4397	0.038*
C6	0.82014 (11)	0.11434 (18)	0.51461 (10)	0.0254 (3)
C7	0.89290 (13)	0.2418 (2)	0.75097 (11)	0.0364 (4)
H7A	0.9484	0.3098	0.7824	0.055*
H7B	0.8979	0.1348	0.7792	0.055*
H7C	0.8330	0.2961	0.7506	0.055*
C8	1.06343 (14)	0.3063 (2)	0.53256 (16)	0.0496 (5)
H8A	1.0423	0.3813	0.4834	0.074*
H8B	1.0956	0.2112	0.5174	0.074*
H8C	1.1087	0.3630	0.5819	0.074*
C9	0.74118 (12)	0.0268 (2)	0.44548 (11)	0.0327 (4)
H9A	0.7578	0.0233	0.3924	0.049*
H9B	0.6800	0.0856	0.4348	0.049*
H9C	0.7345	−0.0852	0.4643	0.049*
C10	0.72773 (10)	0.08517 (17)	0.62059 (10)	0.0223 (3)
H10A	0.7491	0.0465	0.6810	0.027*
H10B	0.6964	−0.0080	0.5834	0.027*
C11	0.65378 (10)	0.22347 (17)	0.61007 (9)	0.0195 (3)
H11	0.6861	0.3218	0.6435	0.023*
C12	0.57030 (10)	0.16888 (16)	0.64028 (9)	0.0195 (3)
H12A	0.5280	0.0943	0.5965	0.023*
H12B	0.5971	0.1057	0.6942	0.023*
C13	0.54069 (11)	0.36552 (19)	0.74324 (9)	0.0253 (3)
H13A	0.5239	0.4819	0.7427	0.038*
H13B	0.6107	0.3523	0.7697	0.038*
H13C	0.5075	0.3040	0.7765	0.038*
C14	0.43142 (10)	0.36483 (16)	0.59459 (9)	0.0175 (3)
C15	0.34745 (10)	0.33743 (15)	0.43473 (9)	0.0177 (3)
C16	0.25039 (10)	0.36157 (17)	0.42568 (10)	0.0228 (3)
H16	0.2307	0.3745	0.4749	0.027*
C17	0.18274 (11)	0.36650 (18)	0.34365 (10)	0.0274 (3)
H17	0.1166	0.3841	0.3374	0.033*
C18	0.20929 (11)	0.34643 (19)	0.27106 (10)	0.0280 (3)
H18	0.1619	0.3497	0.2155	0.034*
C19	0.30580 (11)	0.32148 (18)	0.28011 (9)	0.0251 (3)
H19	0.3249	0.3065	0.2307	0.030*
C20	0.37432 (10)	0.31839 (16)	0.36127 (9)	0.0212 (3)
H20	0.4405	0.3031	0.3671	0.025*

	U11	U22	U33	U12	U13	U23
S1	0.0242 (2)	0.02255 (18)	0.0209 (2)	0.00347 (13)	0.01083 (14)	0.00010 (13)
O1	0.0211 (5)	0.0255 (5)	0.0227 (5)	0.0022 (4)	0.0102 (4)	0.0086 (4)
N1	0.0209 (6)	0.0219 (6)	0.0169 (6)	0.0021 (4)	0.0072 (5)	0.0012 (4)
N2	0.0176 (6)	0.0247 (6)	0.0176 (6)	0.0025 (5)	0.0074 (5)	0.0004 (5)
C1	0.0210 (7)	0.0185 (6)	0.0264 (7)	0.0061 (5)	0.0092 (6)	0.0057 (5)
C2	0.0215 (7)	0.0253 (7)	0.0294 (8)	0.0078 (6)	0.0056 (6)	0.0039 (6)
C3	0.0195 (7)	0.0279 (8)	0.0450 (10)	0.0049 (6)	0.0057 (7)	0.0036 (7)
C4	0.0255 (8)	0.0285 (8)	0.0531 (11)	0.0098 (6)	0.0196 (7)	0.0149 (7)
C5	0.0342 (9)	0.0333 (8)	0.0348 (9)	0.0116 (7)	0.0203 (7)	0.0108 (7)
C6	0.0267 (8)	0.0221 (7)	0.0285 (8)	0.0090 (6)	0.0105 (6)	0.0062 (6)
C7	0.0317 (9)	0.0433 (10)	0.0289 (9)	0.0076 (7)	0.0029 (7)	−0.0013 (7)
C8	0.0328 (10)	0.0438 (11)	0.0815 (16)	0.0091 (8)	0.0315 (10)	0.0224 (10)
C9	0.0361 (9)	0.0370 (9)	0.0247 (8)	0.0071 (7)	0.0096 (7)	−0.0018 (7)
C10	0.0236 (7)	0.0190 (6)	0.0257 (7)	0.0040 (5)	0.0101 (6)	0.0064 (5)
C11	0.0198 (7)	0.0193 (6)	0.0201 (7)	0.0017 (5)	0.0074 (5)	0.0045 (5)
C12	0.0197 (7)	0.0186 (6)	0.0211 (7)	0.0013 (5)	0.0080 (5)	0.0039 (5)
C13	0.0280 (8)	0.0306 (8)	0.0167 (7)	−0.0006 (6)	0.0064 (6)	−0.0002 (6)
C14	0.0192 (7)	0.0162 (6)	0.0188 (7)	−0.0029 (5)	0.0086 (5)	0.0009 (5)
C15	0.0200 (7)	0.0148 (6)	0.0183 (7)	−0.0014 (5)	0.0061 (5)	−0.0005 (5)
C16	0.0215 (7)	0.0233 (7)	0.0246 (7)	−0.0015 (5)	0.0089 (6)	−0.0005 (6)
C17	0.0185 (7)	0.0290 (8)	0.0315 (8)	−0.0016 (6)	0.0039 (6)	0.0005 (6)
C18	0.0272 (8)	0.0293 (8)	0.0218 (8)	−0.0048 (6)	0.0000 (6)	0.0012 (6)
C19	0.0311 (8)	0.0259 (7)	0.0177 (7)	−0.0043 (6)	0.0070 (6)	−0.0006 (6)
C20	0.0220 (7)	0.0207 (6)	0.0220 (7)	−0.0019 (5)	0.0086 (6)	−0.0011 (5)

S1—C14	1.6885 (14)	C8—H8C	0.9800
O1—C11	1.4353 (17)	C9—H9A	0.9800
O1—H1	0.826 (9)	C9—H9B	0.9800
N1—C14	1.3583 (17)	C9—H9C	0.9800
N1—C13	1.4544 (18)	C10—C11	1.5333 (19)
N1—C12	1.4730 (17)	C10—H10A	0.9900
N2—C14	1.3578 (18)	C10—H10B	0.9900
N2—C15	1.4086 (17)	C11—C12	1.5275 (19)
N2—H2	0.875 (9)	C11—H11	1.0000
C1—C6	1.404 (2)	C12—H12A	0.9900
C1—C2	1.405 (2)	C12—H12B	0.9900
C1—C10	1.5130 (19)	C13—H13A	0.9800
C2—C3	1.390 (2)	C13—H13B	0.9800
C2—C7	1.512 (2)	C13—H13C	0.9800
C3—C4	1.387 (3)	C15—C16	1.393 (2)
C3—H3	0.9500	C15—C20	1.396 (2)
C4—C5	1.383 (3)	C16—C17	1.389 (2)
C4—C8	1.513 (2)	C16—H16	0.9500
C5—C6	1.391 (2)	C17—C18	1.380 (2)
C5—H5	0.9500	C17—H17	0.9500
C6—C9	1.510 (2)	C18—C19	1.386 (2)
C7—H7A	0.9800	C18—H18	0.9500
C7—H7B	0.9800	C19—C20	1.3835 (19)
C7—H7C	0.9800	C19—H19	0.9500
C8—H8A	0.9800	C20—H20	0.9500
C8—H8B	0.9800
C11—O1—H1	114.3 (14)	C1—C10—H10A	109.1
C14—N1—C13	120.79 (12)	C11—C10—H10A	109.1
C14—N1—C12	124.00 (12)	C1—C10—H10B	109.1
C13—N1—C12	115.16 (11)	C11—C10—H10B	109.1
C14—N2—C15	131.51 (12)	H10A—C10—H10B	107.9
C14—N2—H2	113.4 (12)	O1—C11—C12	105.77 (11)
C15—N2—H2	113.7 (12)	O1—C11—C10	110.52 (11)
C6—C1—C2	119.22 (14)	C12—C11—C10	111.01 (11)
C6—C1—C10	121.17 (13)	O1—C11—H11	109.8
C2—C1—C10	119.61 (13)	C12—C11—H11	109.8
C3—C2—C1	119.47 (15)	C10—C11—H11	109.8
C3—C2—C7	118.83 (15)	N1—C12—C11	114.64 (11)
C1—C2—C7	121.68 (14)	N1—C12—H12A	108.6
C4—C3—C2	121.91 (16)	C11—C12—H12A	108.6
C4—C3—H3	119.0	N1—C12—H12B	108.6
C2—C3—H3	119.0	C11—C12—H12B	108.6
C5—C4—C3	117.90 (15)	H12A—C12—H12B	107.6
C5—C4—C8	120.58 (17)	N1—C13—H13A	109.5
C3—C4—C8	121.51 (18)	N1—C13—H13B	109.5
C4—C5—C6	122.24 (16)	H13A—C13—H13B	109.5
C4—C5—H5	118.9	N1—C13—H13C	109.5
C6—C5—H5	118.9	H13A—C13—H13C	109.5
C5—C6—C1	119.24 (15)	H13B—C13—H13C	109.5
C5—C6—C9	118.75 (15)	N2—C14—N1	113.87 (12)
C1—C6—C9	122.01 (14)	N2—C14—S1	123.98 (10)
C2—C7—H7A	109.5	N1—C14—S1	122.12 (10)
C2—C7—H7B	109.5	C16—C15—C20	119.25 (13)
H7A—C7—H7B	109.5	C16—C15—N2	125.74 (13)
C2—C7—H7C	109.5	C20—C15—N2	114.87 (12)
H7A—C7—H7C	109.5	C17—C16—C15	119.10 (14)
H7B—C7—H7C	109.5	C17—C16—H16	120.4
C4—C8—H8A	109.5	C15—C16—H16	120.4
C4—C8—H8B	109.5	C18—C17—C16	121.61 (14)
H8A—C8—H8B	109.5	C18—C17—H17	119.2
C4—C8—H8C	109.5	C16—C17—H17	119.2
H8A—C8—H8C	109.5	C17—C18—C19	119.26 (14)
H8B—C8—H8C	109.5	C17—C18—H18	120.4
C6—C9—H9A	109.5	C19—C18—H18	120.4
C6—C9—H9B	109.5	C20—C19—C18	119.91 (14)
H9A—C9—H9B	109.5	C20—C19—H19	120.0
C6—C9—H9C	109.5	C18—C19—H19	120.0
H9A—C9—H9C	109.5	C19—C20—C15	120.85 (13)
H9B—C9—H9C	109.5	C19—C20—H20	119.6
C1—C10—C11	112.30 (11)	C15—C20—H20	119.6
C6—C1—C2—C3	1.4 (2)	C14—N1—C12—C11	90.19 (16)
C10—C1—C2—C3	−177.61 (13)	C13—N1—C12—C11	−92.18 (14)
C6—C1—C2—C7	−177.09 (13)	O1—C11—C12—N1	−76.40 (14)
C10—C1—C2—C7	3.9 (2)	C10—C11—C12—N1	163.70 (12)
C1—C2—C3—C4	−1.5 (2)	C15—N2—C14—N1	170.80 (13)
C7—C2—C3—C4	177.01 (14)	C15—N2—C14—S1	−10.8 (2)
C2—C3—C4—C5	0.5 (2)	C13—N1—C14—N2	167.94 (12)
C2—C3—C4—C8	−178.50 (15)	C12—N1—C14—N2	−14.56 (18)
C3—C4—C5—C6	0.6 (2)	C13—N1—C14—S1	−10.48 (18)
C8—C4—C5—C6	179.65 (15)	C12—N1—C14—S1	167.02 (10)
C4—C5—C6—C1	−0.7 (2)	C14—N2—C15—C16	−22.3 (2)
C4—C5—C6—C9	−179.63 (14)	C14—N2—C15—C20	162.14 (13)
C2—C1—C6—C5	−0.3 (2)	C20—C15—C16—C17	−0.2 (2)
C10—C1—C6—C5	178.68 (13)	N2—C15—C16—C17	−175.56 (13)
C2—C1—C6—C9	178.57 (13)	C15—C16—C17—C18	0.7 (2)
C10—C1—C6—C9	−2.4 (2)	C16—C17—C18—C19	−0.3 (2)
C6—C1—C10—C11	−94.33 (16)	C17—C18—C19—C20	−0.6 (2)
C2—C1—C10—C11	84.66 (16)	C18—C19—C20—C15	1.1 (2)
C1—C10—C11—O1	67.26 (15)	C16—C15—C20—C19	−0.7 (2)
C1—C10—C11—C12	−175.70 (12)	N2—C15—C20—C19	175.19 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···S1i	0.83 (1)	2.50 (1)	3.219 (1)	146 (2)
N2—H2···O1	0.88 (1)	1.89 (1)	2.739 (2)	165 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯S1i	0.83 (1)	2.50 (1)	3.219 (1)	146 (2)
N2—H2⋯O1	0.88 (1)	1.89 (1)	2.739 (2)	165 (2)

Symmetry code: (i) .