N-(4-Chloro-butano-yl)-N'-(2,5-dimeth-oxy-phen-yl)thio-urea.

The title mol-ecule, C(13)H(17)ClN(2)O(3)S, shows an anti and syn disposition of the butanoyl and 2,5-dimethoxyphenyl groups with respect to the thione and is stabilized by intra-molecular N-H⋯O and weak C-H⋯S hydrogen bonds. In the crystal, inter-molecular N-H⋯S hydrogen bonds link the mol-ecules into centrosymmetric dimers. The crystal structure is stabilized by weak C-H⋯O and C-H⋯S contacts.

Related literature

For the structures of related thio­ureas, see: Yamin et al. (2011 ▶); Yusof et al. (2011 ▶).

Experimental

Crystal data

C13H17ClN2O3S

M = 316.80

Triclinic,

a = 7.6882 (18) Å

b = 9.151 (2) Å

c = 10.939 (3) Å

α = 98.536 (5)°

β = 97.787 (5)°

γ = 101.489 (5)°

V = 734.9 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.41 mm−1

T = 298 K

0.29 × 0.25 × 0.19 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.890, T max = 0.926

9303 measured reflections

3351 independent reflections

2928 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.105

S = 1.06

3351 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.22 e Å−3

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 datablock(s) global, I. DOI: 10.1107/S1600536811036002/bh2378sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811036002/bh2378Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811036002/bh2378Isup3.cml

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

C13H17ClN2O3S	Z = 2
Mr = 316.80	F(000) = 332
Triclinic, P1	Dx = 1.432 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.6882 (18) Å	Cell parameters from 934 reflections
b = 9.151 (2) Å	θ = 1.9–27.5°
c = 10.939 (3) Å	µ = 0.41 mm−1
α = 98.536 (5)°	T = 298 K
β = 97.787 (5)°	Slab, colourless
γ = 101.489 (5)°	0.29 × 0.25 × 0.19 mm
V = 734.9 (3) Å3

Bruker SMART APEX CCD area-detector diffractometer	3351 independent reflections
Radiation source: fine-focus sealed tube	2928 reflections with I > 2/s(I)
graphite	Rint = 0.018
Detector resolution: 83.66 pixels mm-1	θmax = 27.5°, θmin = 1.9°
ω scan	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2000)	k = −11→11
Tmin = 0.890, Tmax = 0.926	l = −14→14
9303 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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.053P)2 + 0.1878P] where P = (Fo2 + 2Fc2)/3
3351 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.22 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
Cl1	0.76739 (8)	0.42437 (6)	0.51080 (5)	0.06766 (17)
S1	0.35046 (6)	0.36496 (4)	1.10956 (4)	0.04799 (14)
O1	0.38199 (19)	0.05467 (12)	0.74925 (12)	0.0523 (3)
O2	0.0551 (2)	−0.00809 (15)	1.36092 (13)	0.0633 (4)
O3	0.23484 (18)	−0.21076 (12)	0.90512 (12)	0.0521 (3)
N1	0.40933 (18)	0.27749 (13)	0.88324 (12)	0.0393 (3)
H1A	0.4464	0.3739	0.8901	0.047*
N2	0.29315 (17)	0.07994 (13)	0.97717 (12)	0.0379 (3)
H2A	0.3046	0.0287	0.9073	0.045*
C1	0.5613 (3)	0.2829 (2)	0.45811 (17)	0.0549 (4)
H1B	0.4647	0.3319	0.4332	0.066*
H1C	0.5743	0.2142	0.3851	0.066*
C2	0.5121 (3)	0.19342 (19)	0.55845 (15)	0.0466 (4)
H2B	0.6092	0.1445	0.5826	0.056*
H2C	0.4052	0.1144	0.5235	0.056*
C3	0.4770 (3)	0.28733 (18)	0.67463 (15)	0.0457 (4)
H3A	0.5857	0.3630	0.7127	0.055*
H3B	0.3837	0.3401	0.6506	0.055*
C4	0.4193 (2)	0.19249 (17)	0.76973 (15)	0.0388 (3)
C5	0.3481 (2)	0.22955 (16)	0.98775 (14)	0.0353 (3)
C6	0.2192 (2)	−0.00946 (16)	1.06058 (14)	0.0356 (3)
C7	0.1739 (2)	0.04605 (17)	1.17392 (15)	0.0414 (3)
H7A	0.1919	0.1500	1.2009	0.050*
C8	0.1013 (2)	−0.05441 (19)	1.24712 (15)	0.0435 (4)
C9	0.0757 (2)	−0.20879 (19)	1.20822 (17)	0.0475 (4)
H9A	0.0292	−0.2752	1.2584	0.057*
C10	0.1191 (2)	−0.26447 (18)	1.09489 (17)	0.0463 (4)
H10A	0.1010	−0.3686	1.0688	0.056*
C11	0.1893 (2)	−0.16674 (17)	1.01961 (15)	0.0394 (3)
C12	0.0271 (3)	0.1408 (2)	1.38725 (18)	0.0584 (5)
H12A	−0.0043	0.1587	1.4693	0.088*
H12B	−0.0689	0.1522	1.3260	0.088*
H12C	0.1354	0.2125	1.3843	0.088*
C13	0.1689 (3)	−0.36576 (19)	0.84650 (18)	0.0540 (4)
H13A	0.2096	−0.3825	0.7675	0.081*
H13B	0.0396	−0.3895	0.8329	0.081*
H13C	0.2130	−0.4296	0.8997	0.081*

	U11	U22	U33	U12	U13	U23
Cl1	0.0734 (3)	0.0600 (3)	0.0700 (3)	0.0030 (2)	0.0293 (3)	0.0139 (2)
S1	0.0672 (3)	0.0281 (2)	0.0468 (2)	−0.00080 (17)	0.0255 (2)	0.00220 (16)
O1	0.0760 (8)	0.0283 (6)	0.0488 (7)	−0.0001 (5)	0.0206 (6)	0.0022 (5)
O2	0.1019 (11)	0.0522 (7)	0.0481 (7)	0.0223 (7)	0.0333 (7)	0.0227 (6)
O3	0.0739 (8)	0.0282 (5)	0.0537 (7)	0.0013 (5)	0.0262 (6)	0.0057 (5)
N1	0.0517 (8)	0.0240 (6)	0.0410 (7)	0.0006 (5)	0.0160 (6)	0.0058 (5)
N2	0.0488 (7)	0.0259 (6)	0.0370 (6)	0.0008 (5)	0.0123 (5)	0.0050 (5)
C1	0.0685 (12)	0.0546 (11)	0.0401 (9)	0.0094 (9)	0.0141 (8)	0.0050 (8)
C2	0.0597 (10)	0.0363 (8)	0.0413 (9)	0.0074 (7)	0.0120 (7)	0.0007 (6)
C3	0.0657 (11)	0.0325 (8)	0.0403 (8)	0.0090 (7)	0.0179 (7)	0.0059 (6)
C4	0.0438 (8)	0.0312 (7)	0.0396 (8)	0.0029 (6)	0.0103 (6)	0.0055 (6)
C5	0.0372 (7)	0.0290 (7)	0.0388 (7)	0.0027 (6)	0.0092 (6)	0.0076 (5)
C6	0.0370 (7)	0.0299 (7)	0.0395 (8)	0.0027 (6)	0.0060 (6)	0.0117 (6)
C7	0.0515 (9)	0.0320 (7)	0.0409 (8)	0.0056 (6)	0.0094 (7)	0.0113 (6)
C8	0.0517 (9)	0.0422 (8)	0.0388 (8)	0.0086 (7)	0.0097 (7)	0.0152 (7)
C9	0.0557 (10)	0.0405 (8)	0.0491 (9)	0.0047 (7)	0.0120 (8)	0.0226 (7)
C10	0.0565 (10)	0.0293 (7)	0.0527 (9)	0.0031 (7)	0.0114 (8)	0.0134 (7)
C11	0.0426 (8)	0.0313 (7)	0.0437 (8)	0.0035 (6)	0.0089 (6)	0.0095 (6)
C12	0.0805 (13)	0.0503 (10)	0.0482 (10)	0.0129 (9)	0.0235 (9)	0.0116 (8)
C13	0.0685 (12)	0.0324 (8)	0.0579 (11)	0.0048 (8)	0.0158 (9)	0.0026 (7)

Cl1—C1	1.798 (2)	C3—C4	1.507 (2)
S1—C5	1.6750 (16)	C3—H3A	0.9700
O1—C4	1.2156 (19)	C3—H3B	0.9700
O2—C8	1.370 (2)	C6—C7	1.385 (2)
O2—C12	1.415 (2)	C6—C11	1.405 (2)
O3—C11	1.370 (2)	C7—C8	1.390 (2)
O3—C13	1.4267 (19)	C7—H7A	0.9300
N1—C4	1.3839 (19)	C8—C9	1.380 (2)
N1—C5	1.3905 (19)	C9—C10	1.378 (3)
N1—H1A	0.8600	C9—H9A	0.9300
N2—C5	1.3324 (18)	C10—C11	1.384 (2)
N2—C6	1.4149 (18)	C10—H10A	0.9300
N2—H2A	0.8600	C12—H12A	0.9600
C1—C2	1.508 (2)	C12—H12B	0.9600
C1—H1B	0.9700	C12—H12C	0.9600
C1—H1C	0.9700	C13—H13A	0.9600
C2—C3	1.513 (2)	C13—H13B	0.9600
C2—H2B	0.9700	C13—H13C	0.9600
C2—H2C	0.9700
C8—O2—C12	117.89 (13)	N1—C5—S1	116.73 (10)
C11—O3—C13	117.32 (13)	C7—C6—C11	119.81 (13)
C4—N1—C5	129.36 (12)	C7—C6—N2	125.40 (13)
C4—N1—H1A	115.3	C11—C6—N2	114.78 (13)
C5—N1—H1A	115.3	C6—C7—C8	119.69 (14)
C5—N2—C6	131.35 (13)	C6—C7—H7A	120.2
C5—N2—H2A	114.3	C8—C7—H7A	120.2
C6—N2—H2A	114.3	O2—C8—C9	116.42 (14)
C2—C1—Cl1	112.05 (13)	O2—C8—C7	123.06 (15)
C2—C1—H1B	109.2	C9—C8—C7	120.50 (15)
Cl1—C1—H1B	109.2	C10—C9—C8	119.96 (15)
C2—C1—H1C	109.2	C10—C9—H9A	120.0
Cl1—C1—H1C	109.2	C8—C9—H9A	120.0
H1B—C1—H1C	107.9	C9—C10—C11	120.59 (15)
C1—C2—C3	114.17 (14)	C9—C10—H10A	119.7
C1—C2—H2B	108.7	C11—C10—H10A	119.7
C3—C2—H2B	108.7	O3—C11—C10	125.02 (14)
C1—C2—H2C	108.7	O3—C11—C6	115.55 (13)
C3—C2—H2C	108.7	C10—C11—C6	119.43 (15)
H2B—C2—H2C	107.6	O2—C12—H12A	109.5
C4—C3—C2	112.46 (13)	O2—C12—H12B	109.5
C4—C3—H3A	109.1	H12A—C12—H12B	109.5
C2—C3—H3A	109.1	O2—C12—H12C	109.5
C4—C3—H3B	109.1	H12A—C12—H12C	109.5
C2—C3—H3B	109.1	H12B—C12—H12C	109.5
H3A—C3—H3B	107.8	O3—C13—H13A	109.5
O1—C4—N1	122.66 (14)	O3—C13—H13B	109.5
O1—C4—C3	123.84 (14)	H13A—C13—H13B	109.5
N1—C4—C3	113.49 (13)	O3—C13—H13C	109.5
N2—C5—N1	115.06 (13)	H13A—C13—H13C	109.5
N2—C5—S1	128.21 (12)	H13B—C13—H13C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1	0.86	1.93	2.663 (2)	141
N2—H2A···O3	0.86	2.15	2.5895 (18)	112
C7—H7A···S1	0.93	2.51	3.1853 (18)	129
N1—H1A···S1i	0.86	2.58	3.4058 (16)	161
C3—H3A···S1i	0.97	2.83	3.5633 (19)	133
C12—H12A···O2ii	0.96	2.50	3.259 (3)	136

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1	0.86	1.93	2.663 (2)	141
C7—H7A⋯S1	0.93	2.51	3.1853 (18)	129
N1—H1A⋯S1i	0.86	2.58	3.4058 (16)	161
C3—H3A⋯S1i	0.97	2.83	3.5633 (19)	133
C12—H12A⋯O2ii	0.96	2.50	3.259 (3)	136

Symmetry codes: (i) ; (ii) .