N-(2,2-Dimethyl-propano-yl)-N'-(2-meth-oxy-phen-yl)thio-urea.

In the title compound, C(13)H(18)N(2)O(2)S, the carbonyl-thio-urea fragment is nearly planar with an r.m.s. deviation of 0.0096 Å. The dihedral angle between carbonyl-thio-urea group and the benzene ring is 19.16 (16)°. There are two intra-molecular N-H⋯O hydrogen bonds, which lead to two pseudo-six-membered rings. Weak intra-molecular C-H⋯S hydrogen bonding also occurs.

Related literature

For related structures, see: Saeed & Flörke (2007 ▶); Yusof et al. (2008 ▶); Shoukat et al. (2007 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C13H18N2O2S

M = 266.35

Orthorhombic,

a = 5.9181 (10) Å

b = 13.492 (2) Å

c = 17.592 (3) Å

V = 1404.7 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 273 K

0.50 × 0.14 × 0.09 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.895, T max = 0.980

8711 measured reflections

2763 independent reflections

2227 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.147

S = 1.13

2763 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.18 e Å−3

Absolute structure: Flack (1983 ▶), 1141

Flack parameter: 0.63 (15)

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

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812010914/bq2346sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812010914/bq2346Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812010914/bq2346Isup3.cml

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

C13H18N2O2S	F(000) = 568
Mr = 266.35	Dx = 1.259 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 770 reflections
a = 5.9181 (10) Å	θ = 1.9–26.0°
b = 13.492 (2) Å	µ = 0.23 mm−1
c = 17.592 (3) Å	T = 273 K
V = 1404.7 (4) Å3	Slab, colourless
Z = 4	0.50 × 0.14 × 0.09 mm

Bruker SMART APEX CCD area-detector diffractometer	2763 independent reflections
Radiation source: fine-focus sealed tube	2227 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
Detector resolution: 83.66 pixels mm-1	θmax = 26.0°, θmin = 1.9°
ω scan	h = −7→6
Absorption correction: multi-scan (SADABS; Bruker, 2000)	k = −16→16
Tmin = 0.895, Tmax = 0.980	l = −20→21
8711 measured 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)] = 0.068	H-atom parameters constrained
wR(F2) = 0.147	w = 1/[σ2(Fo2) + (0.0655P)2 + 0.2181P] where P = (Fo2 + 2Fc2)/3
S = 1.13	(Δ/σ)max < 0.001
2763 reflections	Δρmax = 0.32 e Å−3
163 parameters	Δρmin = −0.18 e Å−3
0 restraints	Absolute structure: Flack (1983), 1141 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.63 (15)

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	0.1312 (2)	0.79180 (7)	0.57763 (7)	0.0693 (4)
O1	0.3640 (5)	0.47260 (17)	0.56305 (13)	0.0559 (7)
O2	0.7537 (5)	0.5571 (2)	0.67865 (15)	0.0662 (8)
C6	0.2391 (6)	0.6781 (2)	0.58348 (19)	0.0442 (8)
N2	0.3935 (5)	0.6446 (2)	0.63138 (15)	0.0453 (7)
H2A	0.4306	0.5836	0.6243	0.054*
N1	0.1602 (5)	0.60835 (18)	0.53095 (15)	0.0427 (7)
H1A	0.0573	0.6290	0.5003	0.051*
C5	0.2250 (6)	0.5112 (2)	0.52178 (18)	0.0384 (8)
C8	0.7025 (7)	0.6429 (3)	0.71748 (19)	0.0474 (9)
C9	0.8272 (8)	0.6805 (3)	0.7766 (2)	0.0623 (11)
H9A	0.9588	0.6489	0.7924	0.075*
C4	0.1096 (6)	0.4544 (2)	0.45732 (18)	0.0445 (8)
C7	0.5083 (7)	0.6910 (2)	0.69201 (17)	0.0434 (9)
C3	0.2134 (8)	0.3508 (3)	0.4531 (2)	0.0682 (12)
H3A	0.1901	0.3171	0.5005	0.102*
H3B	0.3724	0.3562	0.4432	0.102*
H3C	0.1427	0.3140	0.4128	0.102*
C2	0.1488 (9)	0.5089 (3)	0.3823 (2)	0.0726 (13)
H2B	0.0831	0.5738	0.3850	0.109*
H2C	0.0798	0.4724	0.3416	0.109*
H2D	0.3082	0.5146	0.3731	0.109*
C12	0.4381 (8)	0.7757 (3)	0.7293 (2)	0.0599 (12)
H12A	0.3061	0.8075	0.7142	0.072*
C11	0.5629 (10)	0.8133 (3)	0.7888 (2)	0.0731 (15)
H11A	0.5165	0.8711	0.8129	0.088*
C10	0.7544 (9)	0.7660 (3)	0.8125 (2)	0.0714 (14)
H10A	0.8365	0.7915	0.8532	0.086*
C13	0.9241 (8)	0.4949 (3)	0.7089 (2)	0.0744 (13)
H13A	0.9422	0.4379	0.6769	0.112*
H13B	0.8817	0.4740	0.7591	0.112*
H13C	1.0642	0.5307	0.7113	0.112*
C1	−0.1417 (7)	0.4454 (3)	0.4742 (3)	0.0734 (12)
H1B	−0.2072	0.5103	0.4777	0.110*
H1C	−0.1626	0.4110	0.5215	0.110*
H1D	−0.2141	0.4090	0.4341	0.110*

	U11	U22	U33	U12	U13	U23
S1	0.0848 (8)	0.0424 (5)	0.0806 (7)	0.0145 (6)	−0.0263 (7)	−0.0102 (5)
O1	0.0650 (17)	0.0465 (13)	0.0562 (14)	0.0105 (13)	−0.0175 (14)	−0.0061 (11)
O2	0.068 (2)	0.0701 (18)	0.0609 (15)	0.0127 (16)	−0.0192 (15)	−0.0080 (14)
C6	0.045 (2)	0.0429 (18)	0.0448 (18)	−0.0036 (16)	0.0009 (18)	0.0016 (15)
N2	0.0535 (19)	0.0360 (14)	0.0465 (16)	0.0025 (14)	−0.0089 (15)	−0.0053 (12)
N1	0.0445 (17)	0.0396 (15)	0.0440 (15)	0.0033 (13)	−0.0109 (14)	−0.0057 (12)
C5	0.0366 (19)	0.0403 (17)	0.0385 (17)	−0.0044 (15)	0.0033 (15)	0.0015 (14)
C8	0.054 (2)	0.048 (2)	0.0405 (18)	−0.0111 (18)	−0.0028 (17)	0.0069 (16)
C9	0.061 (3)	0.074 (3)	0.051 (2)	−0.020 (2)	−0.010 (2)	0.008 (2)
C4	0.039 (2)	0.0484 (19)	0.0462 (19)	−0.0020 (17)	0.0003 (16)	−0.0068 (15)
C7	0.057 (2)	0.0386 (18)	0.0351 (18)	−0.0119 (18)	−0.0021 (17)	0.0025 (14)
C3	0.074 (3)	0.057 (2)	0.074 (3)	0.002 (2)	−0.016 (2)	−0.027 (2)
C2	0.100 (4)	0.078 (3)	0.039 (2)	−0.011 (3)	−0.004 (2)	−0.0070 (19)
C12	0.085 (3)	0.050 (2)	0.045 (2)	−0.007 (2)	−0.003 (2)	−0.0055 (17)
C11	0.119 (5)	0.050 (2)	0.050 (2)	−0.015 (3)	−0.002 (3)	−0.0072 (18)
C10	0.100 (4)	0.068 (3)	0.046 (2)	−0.041 (3)	−0.016 (3)	0.000 (2)
C13	0.063 (3)	0.088 (3)	0.073 (3)	0.012 (2)	−0.007 (2)	0.008 (2)
C1	0.051 (3)	0.080 (3)	0.090 (3)	−0.014 (2)	−0.002 (2)	−0.021 (2)

S1—C6	1.665 (3)	C7—C12	1.382 (5)
O1—C5	1.215 (4)	C3—H3A	0.9600
O2—C8	1.378 (5)	C3—H3B	0.9600
O2—C13	1.416 (5)	C3—H3C	0.9600
C6—N2	1.323 (4)	C2—H2B	0.9600
C6—N1	1.399 (4)	C2—H2C	0.9600
N2—C7	1.411 (4)	C2—H2D	0.9600
N2—H2A	0.8600	C12—C11	1.378 (6)
N1—C5	1.375 (4)	C12—H12A	0.9300
N1—H1A	0.8600	C11—C10	1.366 (7)
C5—C4	1.530 (5)	C11—H11A	0.9300
C8—C9	1.373 (5)	C10—H10A	0.9300
C8—C7	1.394 (5)	C13—H13A	0.9600
C9—C10	1.385 (6)	C13—H13B	0.9600
C9—H9A	0.9300	C13—H13C	0.9600
C4—C1	1.522 (5)	C1—H1B	0.9600
C4—C2	1.529 (5)	C1—H1C	0.9600
C4—C3	1.529 (5)	C1—H1D	0.9600
C8—O2—C13	117.9 (3)	C4—C3—H3C	109.5
N2—C6—N1	114.9 (3)	H3A—C3—H3C	109.5
N2—C6—S1	128.3 (3)	H3B—C3—H3C	109.5
N1—C6—S1	116.8 (3)	C4—C2—H2B	109.5
C6—N2—C7	131.5 (3)	C4—C2—H2C	109.5
C6—N2—H2A	114.3	H2B—C2—H2C	109.5
C7—N2—H2A	114.3	C4—C2—H2D	109.5
C5—N1—C6	128.7 (3)	H2B—C2—H2D	109.5
C5—N1—H1A	115.7	H2C—C2—H2D	109.5
C6—N1—H1A	115.7	C11—C12—C7	120.2 (4)
O1—C5—N1	121.9 (3)	C11—C12—H12A	119.9
O1—C5—C4	122.0 (3)	C7—C12—H12A	119.9
N1—C5—C4	116.1 (3)	C10—C11—C12	120.4 (4)
C9—C8—O2	124.6 (4)	C10—C11—H11A	119.8
C9—C8—C7	121.0 (4)	C12—C11—H11A	119.8
O2—C8—C7	114.4 (3)	C11—C10—C9	120.5 (4)
C8—C9—C10	119.1 (4)	C11—C10—H10A	119.7
C8—C9—H9A	120.5	C9—C10—H10A	119.7
C10—C9—H9A	120.5	O2—C13—H13A	109.5
C1—C4—C2	110.8 (4)	O2—C13—H13B	109.5
C1—C4—C3	109.2 (3)	H13A—C13—H13B	109.5
C2—C4—C3	109.6 (3)	O2—C13—H13C	109.5
C1—C4—C5	109.4 (3)	H13A—C13—H13C	109.5
C2—C4—C5	109.4 (3)	H13B—C13—H13C	109.5
C3—C4—C5	108.4 (3)	C4—C1—H1B	109.5
C12—C7—C8	118.7 (3)	C4—C1—H1C	109.5
C12—C7—N2	125.5 (4)	H1B—C1—H1C	109.5
C8—C7—N2	115.7 (3)	C4—C1—H1D	109.5
C4—C3—H3A	109.5	H1B—C1—H1D	109.5
C4—C3—H3B	109.5	H1C—C1—H1D	109.5
H3A—C3—H3B	109.5
N1—C6—N2—C7	−178.8 (3)	O1—C5—C4—C3	−4.2 (5)
S1—C6—N2—C7	2.0 (6)	N1—C5—C4—C3	176.6 (3)
N2—C6—N1—C5	−1.5 (5)	C9—C8—C7—C12	−2.3 (5)
S1—C6—N1—C5	177.9 (3)	O2—C8—C7—C12	177.6 (3)
C6—N1—C5—O1	2.2 (5)	C9—C8—C7—N2	−179.4 (3)
C6—N1—C5—C4	−178.6 (3)	O2—C8—C7—N2	0.5 (4)
C13—O2—C8—C9	10.6 (5)	C6—N2—C7—C12	19.9 (6)
C13—O2—C8—C7	−169.3 (3)	C6—N2—C7—C8	−163.3 (3)
O2—C8—C9—C10	−178.1 (3)	C8—C7—C12—C11	2.2 (6)
C7—C8—C9—C10	1.7 (5)	N2—C7—C12—C11	178.9 (3)
O1—C5—C4—C1	114.7 (4)	C7—C12—C11—C10	−1.4 (6)
N1—C5—C4—C1	−64.5 (4)	C12—C11—C10—C9	0.8 (6)
O1—C5—C4—C2	−123.7 (4)	C8—C9—C10—C11	−1.0 (6)
N1—C5—C4—C2	57.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1	0.86	1.89	2.619 (4)	142
N2—H2A···O2	0.86	2.17	2.575 (4)	109
C12—H12A···S1	0.93	2.62	3.235 (4)	124

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1	0.86	1.89	2.619 (4)	142
N2—H2A⋯O2	0.86	2.17	2.575 (4)	109
C12—H12A⋯S1	0.93	2.62	3.235 (4)	124