Butyl 2-(3-benzoyl-thio-ureido)acetate.

In the title compound, C(14)H(18)N(2)O(3)S, the butyl acetate fragment and the benzoyl group adopt a cis-trans configuration, respectively, with respect to the thiono S atom across the C-N bonds. In the crystal packing, the mol-ecules are linked by inter-molecular N-H⋯O and C-H⋯O hydrogen bonds to form a one-dimensional chain along the c axis. The terminal butyl C atom is disordered with occupancies 0.82 (2)and 0.18 (2).

Related literature

For information on bond lengths, see: Allen et al. (1987 ▶); For related structures, see: Hassan et al. (2008a ▶,b ▶); Yamin & Hassan (2004 ▶); Yamin & Yusof (2003 ▶).

Experimental

Crystal data

C14H18N2O3S

M = 294.36

Monoclinic,

a = 14.051 (3) Å

b = 7.9482 (18) Å

c = 14.116 (3) Å

β = 102.753 (3)°

V = 1537.5 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 298 (2) K

0.46 × 0.28 × 0.25 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.906, T max = 0.947

7933 measured reflections

2853 independent reflections

2098 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.136

S = 1.03

2853 reflections

187 parameters

6 restraints

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.27 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, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808033540/at2648sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808033540/at2648Isup2.hkl

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

C14H18N2O3S	F(000) = 624
Mr = 294.36	Dx = 1.272 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2213 reflections
a = 14.051 (3) Å	θ = 3.0–25.5°
b = 7.9482 (18) Å	µ = 0.22 mm−1
c = 14.116 (3) Å	T = 298 K
β = 102.753 (3)°	Block, colourless
V = 1537.5 (6) Å3	0.46 × 0.28 × 0.25 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	2853 independent reflections
Radiation source: fine-focus sealed tube	2098 reflections with I > 2σ(I)
graphite	Rint = 0.022
ω scans	θmax = 25.5°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −17→15
Tmin = 0.906, Tmax = 0.947	k = −9→9
7933 measured reflections	l = −17→16

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0696P)2 + 0.3732P] where P = (Fo2 + 2Fc2)/3
2853 reflections	(Δ/σ)max < 0.001
187 parameters	Δρmax = 0.24 e Å−3
6 restraints	Δρmin = −0.26 e Å−3

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	Occ. (<1)
C5	0.38240 (15)	0.4009 (3)	0.51713 (17)	0.0528 (6)
H5	0.3785	0.4057	0.4506	0.063*
C4	0.31404 (17)	0.4833 (3)	0.55659 (18)	0.0588 (6)
H4	0.2645	0.5445	0.5167	0.071*
C3	0.31902 (17)	0.4750 (3)	0.65504 (18)	0.0606 (6)
H3	0.2730	0.5312	0.6816	0.073*
C2	0.39148 (17)	0.3842 (3)	0.71373 (17)	0.0626 (7)
H2	0.3936	0.3768	0.7799	0.075*
C1	0.46139 (16)	0.3037 (3)	0.67530 (16)	0.0545 (6)
H1	0.5114	0.2445	0.7158	0.065*
C6	0.45697 (14)	0.3111 (3)	0.57640 (15)	0.0460 (5)
C7	0.52769 (15)	0.2248 (3)	0.52830 (15)	0.0480 (5)
C8	0.69838 (15)	0.1216 (3)	0.55880 (15)	0.0477 (5)
C9	0.75837 (16)	−0.0258 (3)	0.43410 (16)	0.0563 (6)
H9A	0.7547	−0.1438	0.4503	0.068*
H9B	0.8220	0.0155	0.4671	0.068*
C10	0.74863 (17)	−0.0094 (3)	0.32743 (17)	0.0526 (5)
C11	0.82911 (19)	−0.0919 (4)	0.20303 (18)	0.0751 (8)
H11A	0.8197	0.0214	0.1771	0.090*
H11B	0.7797	−0.1641	0.1645	0.090*
C12	0.92815 (19)	−0.1537 (4)	0.1994 (2)	0.0751 (8)
H12A	0.9353	−0.2686	0.2231	0.090*
H12B	0.9765	−0.0855	0.2424	0.090*
C13	0.9475 (2)	−0.1483 (5)	0.0995 (2)	0.0897 (9)
H13A	0.9217	−0.2484	0.0637	0.108*
H13B	0.9161	−0.0507	0.0648	0.108*
C14'	1.050 (2)	−0.139 (7)	0.108 (2)	0.111 (3)	0.18 (2)
H14E	1.0727	−0.0282	0.1288	0.166*	0.18 (2)
H14F	1.0652	−0.1633	0.0466	0.166*	0.18 (2)
H14D	1.0819	−0.2199	0.1554	0.166*	0.18 (2)
C14	1.0392 (5)	−0.2373 (17)	0.0885 (5)	0.111 (3)	0.82 (2)
H14B	1.0456	−0.2286	0.0223	0.166*	0.82 (2)
H14A	1.0356	−0.3537	0.1055	0.166*	0.82 (2)
H14C	1.0947	−0.1862	0.1306	0.166*	0.82 (2)
S1	0.80227 (5)	0.10476 (11)	0.64102 (5)	0.0744 (3)
O1	0.50502 (11)	0.1805 (2)	0.44383 (11)	0.0647 (5)
O2	0.68594 (12)	0.0656 (2)	0.27269 (13)	0.0709 (5)
O3	0.82116 (12)	−0.0935 (2)	0.30338 (11)	0.0648 (5)
N1	0.61986 (12)	0.2016 (2)	0.58446 (12)	0.0492 (5)
H1A	0.6302	0.2413	0.6425	0.059*
N2	0.68439 (13)	0.0652 (2)	0.46870 (13)	0.0517 (5)
H2A	0.6292	0.0835	0.4295	0.062*

	U11	U22	U33	U12	U13	U23
C5	0.0497 (12)	0.0591 (14)	0.0492 (13)	−0.0022 (11)	0.0100 (10)	0.0037 (11)
C4	0.0504 (13)	0.0584 (15)	0.0658 (15)	0.0052 (11)	0.0090 (11)	0.0063 (12)
C3	0.0552 (14)	0.0631 (16)	0.0670 (16)	0.0002 (11)	0.0209 (12)	−0.0101 (12)
C2	0.0611 (15)	0.0801 (18)	0.0481 (13)	−0.0007 (13)	0.0154 (11)	−0.0050 (12)
C1	0.0499 (12)	0.0630 (15)	0.0481 (13)	0.0003 (11)	0.0057 (10)	0.0024 (11)
C6	0.0421 (11)	0.0488 (12)	0.0463 (12)	−0.0056 (9)	0.0077 (9)	−0.0015 (10)
C7	0.0460 (12)	0.0511 (13)	0.0459 (12)	−0.0034 (10)	0.0076 (9)	0.0015 (10)
C8	0.0470 (12)	0.0481 (13)	0.0495 (13)	−0.0026 (10)	0.0137 (10)	0.0069 (10)
C9	0.0539 (13)	0.0606 (15)	0.0566 (14)	0.0078 (11)	0.0171 (11)	0.0027 (11)
C10	0.0485 (12)	0.0540 (14)	0.0575 (14)	−0.0006 (11)	0.0162 (11)	−0.0009 (11)
C11	0.0707 (17)	0.101 (2)	0.0565 (15)	0.0157 (15)	0.0201 (13)	−0.0033 (14)
C12	0.0645 (16)	0.092 (2)	0.0718 (17)	0.0078 (14)	0.0222 (13)	−0.0051 (15)
C13	0.087 (2)	0.110 (2)	0.0789 (19)	0.0225 (18)	0.0322 (16)	0.0006 (17)
C14'	0.104 (3)	0.147 (7)	0.093 (3)	0.051 (4)	0.048 (3)	0.010 (4)
C14	0.104 (3)	0.147 (7)	0.093 (3)	0.051 (4)	0.048 (3)	0.010 (4)
S1	0.0534 (4)	0.1112 (6)	0.0549 (4)	0.0174 (4)	0.0040 (3)	−0.0017 (4)
O1	0.0538 (9)	0.0881 (12)	0.0482 (10)	0.0065 (9)	0.0030 (7)	−0.0130 (9)
O2	0.0631 (11)	0.0901 (13)	0.0620 (11)	0.0204 (10)	0.0188 (9)	0.0141 (9)
O3	0.0613 (10)	0.0803 (12)	0.0557 (10)	0.0175 (9)	0.0195 (8)	−0.0007 (8)
N1	0.0449 (10)	0.0609 (12)	0.0418 (9)	0.0013 (9)	0.0096 (7)	−0.0019 (8)
N2	0.0454 (10)	0.0605 (12)	0.0494 (11)	0.0029 (9)	0.0109 (8)	−0.0034 (9)

C5—C4	1.377 (3)	C10—O2	1.195 (3)
C5—C6	1.386 (3)	C10—O3	1.324 (3)
C5—H5	0.9300	C11—O3	1.445 (3)
C4—C3	1.378 (3)	C11—C12	1.487 (4)
C4—H4	0.9300	C11—H11A	0.9700
C3—C2	1.368 (3)	C11—H11B	0.9700
C3—H3	0.9300	C12—C13	1.494 (4)
C2—C1	1.380 (3)	C12—H12A	0.9700
C2—H2	0.9300	C12—H12B	0.9700
C1—C6	1.385 (3)	C13—C14'	1.42 (3)
C1—H1	0.9300	C13—C14	1.507 (7)
C6—C7	1.489 (3)	C13—H13A	0.9700
C7—O1	1.216 (2)	C13—H13B	0.9700
C7—N1	1.373 (3)	C14'—H14E	0.9600
C8—N2	1.322 (3)	C14'—H14F	0.9600
C8—N1	1.389 (3)	C14'—H14D	0.9600
C8—S1	1.658 (2)	C14—H14B	0.9600
C9—N2	1.437 (3)	C14—H14A	0.9600
C9—C10	1.487 (3)	C14—H14C	0.9600
C9—H9A	0.9700	N1—H1A	0.8600
C9—H9B	0.9700	N2—H2A	0.8600
C4—C5—C6	120.2 (2)	O3—C11—H11B	110.1
C4—C5—H5	119.9	C12—C11—H11B	110.1
C6—C5—H5	119.9	H11A—C11—H11B	108.5
C5—C4—C3	120.0 (2)	C11—C12—C13	112.9 (2)
C5—C4—H4	120.0	C11—C12—H12A	109.0
C3—C4—H4	120.0	C13—C12—H12A	109.0
C2—C3—C4	120.1 (2)	C11—C12—H12B	109.0
C2—C3—H3	120.0	C13—C12—H12B	109.0
C4—C3—H3	120.0	H12A—C12—H12B	107.8
C3—C2—C1	120.4 (2)	C14'—C13—C12	108.2 (12)
C3—C2—H2	119.8	C14'—C13—C14	32.8 (19)
C1—C2—H2	119.8	C12—C13—C14	115.0 (3)
C2—C1—C6	119.9 (2)	C14'—C13—H13A	110.1
C2—C1—H1	120.0	C12—C13—H13A	110.1
C6—C1—H1	120.0	C14—C13—H13A	77.9
C1—C6—C5	119.4 (2)	C14'—C13—H13B	110.1
C1—C6—C7	123.66 (19)	C12—C13—H13B	110.1
C5—C6—C7	116.99 (19)	C14—C13—H13B	128.8
O1—C7—N1	122.4 (2)	H13A—C13—H13B	108.4
O1—C7—C6	121.58 (19)	C13—C14'—H14E	109.5
N1—C7—C6	115.97 (18)	C13—C14'—H14F	109.5
N2—C8—N1	116.64 (19)	C13—C14'—H14D	109.5
N2—C8—S1	124.56 (17)	C13—C14—H14B	109.5
N1—C8—S1	118.80 (16)	C13—C14—H14A	109.5
N2—C9—C10	112.83 (19)	H14B—C14—H14A	109.5
N2—C9—H9A	109.0	C13—C14—H14C	109.5
C10—C9—H9A	109.0	H14B—C14—H14C	109.5
N2—C9—H9B	109.0	H14A—C14—H14C	109.5
C10—C9—H9B	109.0	C10—O3—C11	118.49 (19)
H9A—C9—H9B	107.8	C7—N1—C8	127.81 (18)
O2—C10—O3	125.8 (2)	C7—N1—H1A	116.1
O2—C10—C9	126.0 (2)	C8—N1—H1A	116.1
O3—C10—C9	108.1 (2)	C8—N2—C9	122.18 (19)
O3—C11—C12	107.8 (2)	C8—N2—H2A	118.9
O3—C11—H11A	110.1	C9—N2—H2A	118.9
C12—C11—H11A	110.1

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2i	0.86	2.39	3.203 (2)	158
N2—H2A···O1	0.86	1.96	2.631 (2)	134
C2—H2···O1i	0.93	2.53	3.328 (3)	144
C9—H9B···S1	0.97	2.63	3.032 (2)	105

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2i	0.86	2.39	3.203 (2)	158
N2—H2A⋯O1	0.86	1.96	2.631 (2)	134
C2—H2⋯O1i	0.93	2.53	3.328 (3)	144

Symmetry code: (i) .