1-(4-Acetyl-phen-yl)-3-butyrylthio-urea.

The title compound, C(13)H(16)N(2)O(2)S, crystallizes in the thio-amide form with an intra-molecular hydrogen bond of type N-H⋯O(butyr-yl). Mol-ecules are linked into chains parallel to [10] by a further hydrogen bond of type N-H⋯O(acet-yl). C-H⋯O and C-H⋯S hydrogen bonds are also present.

Related literature

For related literature, see: D’hooghe et al. (2005 ▶); Glasser & Doughty (1964 ▶); Huebner et al. (1953 ▶); Jain & Rao (2003 ▶); Morales et al. (2000 ▶); Ru et al. (1994 ▶); Xu et al. (2004 ▶); Xue et al. (2003 ▶); Zeng et al. (2003 ▶); Zheng et al. (2004 ▶); Douglas & Dains (1934 ▶).

Experimental

Crystal data

C13H16N2O2S

M = 264.34

Triclinic,

a = 7.5111 (5) Å

b = 9.7585 (8) Å

c = 10.5036 (5) Å

α = 65.283 (5)°

β = 76.245 (4)°

γ = 68.589 (5)°

V = 647.78 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.25 mm−1

T = 100 (2) K

0.35 × 0.20 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur S diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 ▶) T min = 0.940, T max = 0.976

22401 measured reflections

3613 independent reflections

3036 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.087

S = 1.06

3613 reflections

173 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.45 e Å−3

Δρmin = −0.22 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP (Siemens, 1994 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808022095/pk2104sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808022095/pk2104Isup2.hkl

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

C13H16N2O2S	Z = 2
Mr = 264.34	F000 = 280
Triclinic, P1	Dx = 1.355 Mg m−3
Hall symbol: -P 1	Melting point: 458 K
a = 7.5111 (5) Å	Mo Kα radiation λ = 0.71073 Å
b = 9.7585 (8) Å	Cell parameters from 13985 reflections
c = 10.5036 (5) Å	θ = 2.6–30.6º
α = 65.283 (5)º	µ = 0.25 mm−1
β = 76.245 (4)º	T = 100 (2) K
γ = 68.589 (5)º	Tablet, pale yellow
V = 647.78 (8) Å3	0.35 × 0.20 × 0.10 mm

Oxford Diffraction Xcalibur S diffractometer	3613 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3036 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.030
Detector resolution: 16 pixels mm-1	θmax = 30.7º
T = 100(2) K	θmin = 2.6º
ω scans	h = −10→10
Absorption correction: multi-scan(CrysAlis RED; Oxford Diffraction, 2008)	k = −13→13
Tmin = 0.940, Tmax = 0.976	l = −15→15
22401 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)] = 0.031	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.087	w = 1/[σ2(Fo2) + (0.0536P)2 + 0.0789P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.003
3613 reflections	Δρmax = 0.45 e Å−3
173 parameters	Δρmin = −0.22 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
S	0.29224 (4)	0.76793 (3)	0.30824 (3)	0.01606 (9)
O1	0.44460 (12)	0.23350 (9)	0.43763 (8)	0.01882 (17)
O2	1.01149 (11)	0.57384 (9)	−0.32905 (8)	0.01832 (17)
N1	0.30196 (13)	0.47376 (10)	0.46308 (9)	0.01281 (18)
H01	0.223 (2)	0.5166 (17)	0.5163 (15)	0.020 (3)*
N2	0.50761 (13)	0.49957 (11)	0.26018 (9)	0.01395 (18)
H02	0.522 (2)	0.4018 (19)	0.2950 (17)	0.032 (4)*
C1	0.19337 (17)	0.00779 (13)	0.85964 (12)	0.0201 (2)
H1A	0.2003	0.0630	0.9169	0.030*
H1B	0.2504	−0.1064	0.9066	0.030*
H1C	0.0587	0.0302	0.8482	0.030*
C2	0.30349 (17)	0.06471 (12)	0.71538 (12)	0.0192 (2)
H2A	0.4416	0.0343	0.7261	0.023*
H2B	0.2907	0.0134	0.6556	0.023*
C3	0.22642 (15)	0.24316 (12)	0.64468 (11)	0.0149 (2)
H3A	0.0909	0.2712	0.6285	0.018*
H3B	0.2281	0.2925	0.7096	0.018*
C4	0.33675 (14)	0.31196 (12)	0.50663 (11)	0.0134 (2)
C5	0.37498 (14)	0.57496 (12)	0.33954 (10)	0.01180 (19)
C6	0.60770 (14)	0.55630 (12)	0.12737 (10)	0.01210 (19)
C7	0.70848 (15)	0.44211 (12)	0.06708 (11)	0.0145 (2)
H7	0.7064	0.3359	0.1171	0.017*
C8	0.81080 (15)	0.48184 (12)	−0.06408 (11)	0.0145 (2)
H8	0.8775	0.4033	−0.1039	0.017*
C9	0.81661 (14)	0.63750 (12)	−0.13858 (11)	0.0126 (2)
C10	0.71839 (15)	0.74982 (12)	−0.07705 (11)	0.0148 (2)
H10	0.7227	0.8555	−0.1264	0.018*
C11	0.61396 (15)	0.71148 (12)	0.05482 (11)	0.0148 (2)
H11	0.5478	0.7900	0.0949	0.018*
C12	0.92871 (14)	0.67675 (12)	−0.27915 (11)	0.0143 (2)
C13	0.93843 (19)	0.84247 (14)	−0.35931 (12)	0.0241 (3)
H13A	1.0270	0.8463	−0.4451	0.036*
H13B	0.9845	0.8759	−0.3005	0.036*
H13C	0.8102	0.9136	−0.3848	0.036*

	U11	U22	U33	U12	U13	U23
S	0.01598 (13)	0.01249 (13)	0.01624 (14)	−0.00382 (9)	0.00445 (9)	−0.00563 (10)
O1	0.0236 (4)	0.0161 (4)	0.0159 (4)	−0.0068 (3)	0.0050 (3)	−0.0081 (3)
O2	0.0209 (4)	0.0178 (4)	0.0143 (4)	−0.0047 (3)	0.0052 (3)	−0.0086 (3)
N1	0.0140 (4)	0.0132 (4)	0.0103 (4)	−0.0044 (3)	0.0036 (3)	−0.0058 (3)
N2	0.0168 (4)	0.0127 (4)	0.0110 (4)	−0.0054 (3)	0.0035 (3)	−0.0050 (3)
C1	0.0255 (5)	0.0160 (5)	0.0161 (5)	−0.0089 (4)	0.0005 (4)	−0.0023 (4)
C2	0.0232 (5)	0.0127 (5)	0.0181 (5)	−0.0055 (4)	0.0031 (4)	−0.0050 (4)
C3	0.0153 (5)	0.0142 (5)	0.0127 (5)	−0.0054 (4)	0.0024 (4)	−0.0037 (4)
C4	0.0137 (4)	0.0148 (5)	0.0120 (5)	−0.0052 (4)	−0.0007 (4)	−0.0048 (4)
C5	0.0112 (4)	0.0149 (5)	0.0100 (5)	−0.0049 (3)	−0.0002 (3)	−0.0048 (4)
C6	0.0117 (4)	0.0153 (5)	0.0095 (4)	−0.0050 (4)	0.0010 (3)	−0.0051 (4)
C7	0.0163 (5)	0.0132 (5)	0.0138 (5)	−0.0052 (4)	0.0017 (4)	−0.0059 (4)
C8	0.0148 (4)	0.0148 (5)	0.0139 (5)	−0.0041 (4)	0.0013 (4)	−0.0072 (4)
C9	0.0124 (4)	0.0155 (5)	0.0099 (5)	−0.0043 (4)	0.0001 (4)	−0.0051 (4)
C10	0.0171 (5)	0.0139 (5)	0.0126 (5)	−0.0054 (4)	0.0017 (4)	−0.0052 (4)
C11	0.0172 (5)	0.0141 (5)	0.0131 (5)	−0.0044 (4)	0.0024 (4)	−0.0073 (4)
C12	0.0143 (4)	0.0165 (5)	0.0112 (5)	−0.0048 (4)	0.0008 (4)	−0.0054 (4)
C13	0.0345 (6)	0.0192 (5)	0.0167 (5)	−0.0126 (5)	0.0104 (5)	−0.0077 (4)

S—C5	1.6629 (11)	C12—C13	1.4993 (15)
O1—C4	1.2246 (13)	N1—H01	0.835 (16)
O2—C12	1.2243 (13)	N2—H02	0.840 (16)
N1—C4	1.3864 (13)	C1—H1A	0.9800
N1—C5	1.3948 (12)	C1—H1B	0.9800
N2—C5	1.3458 (13)	C1—H1C	0.9800
N2—C6	1.4061 (12)	C2—H2A	0.9900
C1—C2	1.5245 (15)	C2—H2B	0.9900
C2—C3	1.5185 (14)	C3—H3A	0.9900
C3—C4	1.5036 (14)	C3—H3B	0.9900
C6—C11	1.3949 (14)	C7—H7	0.9500
C6—C7	1.4008 (14)	C8—H8	0.9500
C7—C8	1.3807 (14)	C10—H10	0.9500
C8—C9	1.3999 (14)	C11—H11	0.9500
C9—C10	1.3923 (14)	C13—H13A	0.9800
C9—C12	1.4856 (14)	C13—H13B	0.9800
C10—C11	1.3921 (14)	C13—H13C	0.9800
C4—N1—C5	128.62 (9)	H1A—C1—H1B	109.5
C5—N2—C6	131.77 (9)	C2—C1—H1C	109.5
C3—C2—C1	110.45 (9)	H1A—C1—H1C	109.5
C4—C3—C2	114.32 (8)	H1B—C1—H1C	109.5
O1—C4—N1	122.98 (9)	C3—C2—H2A	109.6
O1—C4—C3	123.40 (9)	C1—C2—H2A	109.6
N1—C4—C3	113.60 (9)	C3—C2—H2B	109.6
N2—C5—N1	113.62 (9)	C1—C2—H2B	109.6
N2—C5—S	128.35 (8)	H2A—C2—H2B	108.1
N1—C5—S	118.03 (7)	C4—C3—H3A	108.7
C11—C6—C7	119.43 (9)	C2—C3—H3A	108.7
C11—C6—N2	125.91 (9)	C4—C3—H3B	108.7
C7—C6—N2	114.66 (9)	C2—C3—H3B	108.7
C8—C7—C6	120.86 (9)	H3A—C3—H3B	107.6
C7—C8—C9	120.25 (10)	C8—C7—H7	119.6
C10—C9—C8	118.54 (9)	C6—C7—H7	119.6
C10—C9—C12	122.35 (9)	C7—C8—H8	119.9
C8—C9—C12	119.11 (9)	C9—C8—H8	119.9
C11—C10—C9	121.78 (9)	C11—C10—H10	119.1
C10—C11—C6	119.12 (9)	C9—C10—H10	119.1
O2—C12—C9	119.80 (9)	C10—C11—H11	120.4
O2—C12—C13	120.49 (9)	C6—C11—H11	120.4
C9—C12—C13	119.71 (9)	C12—C13—H13A	109.5
C4—N1—H01	115.4 (10)	C12—C13—H13B	109.5
C5—N1—H01	115.9 (10)	H13A—C13—H13B	109.5
C5—N2—H02	111.5 (11)	C12—C13—H13C	109.5
C6—N2—H02	116.4 (11)	H13A—C13—H13C	109.5
C2—C1—H1A	109.5	H13B—C13—H13C	109.5
C2—C1—H1B	109.5
C1—C2—C3—C4	175.26 (9)	C6—C7—C8—C9	0.55 (16)
C5—N1—C4—O1	0.85 (17)	C7—C8—C9—C10	0.39 (15)
C5—N1—C4—C3	−177.92 (9)	C7—C8—C9—C12	179.66 (9)
C2—C3—C4—O1	18.45 (15)	C8—C9—C10—C11	−0.70 (16)
C2—C3—C4—N1	−162.79 (9)	C12—C9—C10—C11	−179.95 (10)
C6—N2—C5—N1	176.36 (10)	C9—C10—C11—C6	0.07 (16)
C6—N2—C5—S	−3.91 (17)	C7—C6—C11—C10	0.87 (15)
C4—N1—C5—N2	−5.70 (15)	N2—C6—C11—C10	−179.38 (10)
C4—N1—C5—S	174.53 (8)	C10—C9—C12—O2	−179.50 (10)
C5—N2—C6—C11	11.68 (18)	C8—C9—C12—O2	1.26 (15)
C5—N2—C6—C7	−168.56 (11)	C10—C9—C12—C13	0.06 (16)
C11—C6—C7—C8	−1.19 (16)	C8—C9—C12—C13	−179.18 (10)
N2—C6—C7—C8	179.03 (9)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H02···O1	0.840 (16)	1.874 (16)	2.6211 (12)	147.4 (16)
N1—H01···O2i	0.835 (16)	2.087 (16)	2.9057 (12)	166.7 (13)
C3—H3B···O2i	0.99	2.54	3.1345 (13)	118
C1—H1C···Sii	0.98	3.01	3.8996 (13)	151
C3—H3A···Sii	0.99	2.92	3.8444 (11)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H02⋯O1	0.840 (16)	1.874 (16)	2.6211 (12)	147.4 (16)
N1—H01⋯O2i	0.835 (16)	2.087 (16)	2.9057 (12)	166.7 (13)
C3—H3B⋯O2i	0.99	2.54	3.1345 (13)	118
C1—H1C⋯Sii	0.98	3.01	3.8996 (13)	151
C3—H3A⋯Sii	0.99	2.92	3.8444 (11)	155

Symmetry codes: (i) ; (ii) .