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

In the title compound, C(11)H(12)N(2)O(3)S, the methyl acetate and benzoyl groups adopt a cis-trans configuration with respect to the thiono S atom across the C-N bonds. An intra-molecular N-H⋯O hydrogen bond is observed. In the crystal packing, mol-ecules are linked by inter-molecular N-H⋯S and C-H⋯O hydrogen bonds to form a two-dimensional network lying parallel to (101).

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Hassan et al. (2008a ▶,b ▶,c ▶); Yamin & Hassan (2004 ▶). For the preparation, see: Hassan et al. (2008a ▶).

Experimental

Crystal data

C11H12N2O3S

M = 252.29

Monoclinic,

a = 14.5804 (15) Å

b = 4.9740 (5) Å

c = 16.9133 (16) Å

β = 96.210 (2)°

V = 1219.4 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 298 K

0.48 × 0.14 × 0.06 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.884, T max = 0.984

6881 measured reflections

2264 independent reflections

1600 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.089

wR(F 2) = 0.172

S = 1.24

2264 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAIn class="Chemical">NT; 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 datablocks global, I. DOI: 10.1107/S1600536809046169/ci2952sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809046169/ci2952Isup2.hkl

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

C11H12N2O3S	F(000) = 528
Mr = 252.29	Dx = 1.374 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 871 reflections
a = 14.5804 (15) Å	θ = 1.8–25.5°
b = 4.9740 (5) Å	µ = 0.26 mm−1
c = 16.9133 (16) Å	T = 298 K
β = 96.210 (2)°	Needle, colourless
V = 1219.4 (2) Å3	0.48 × 0.14 × 0.06 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	2264 independent reflections
Radiation source: fine-focus sealed tube	1600 reflections with I > 2σ(I)
graphite	Rint = 0.048
ω scans	θmax = 25.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −17→17
Tmin = 0.884, Tmax = 0.984	k = −5→6
6881 measured reflections	l = −17→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)] = 0.089	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.172	H-atom parameters constrained
S = 1.24	w = 1/[σ2(Fo2) + (0.0474P)2 + 0.746P] where P = (Fo2 + 2Fc2)/3
2264 reflections	(Δ/σ)max = 0.001
154 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.18 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
S1	0.50901 (8)	0.0880 (3)	0.62465 (7)	0.0818 (5)
O1	0.2035 (2)	0.1002 (7)	0.53998 (17)	0.0725 (10)
N1	0.3541 (2)	−0.0034 (7)	0.53458 (18)	0.0545 (9)
H1A	0.3909	−0.0822	0.5055	0.065*
C9	0.3780 (3)	0.4046 (9)	0.7161 (2)	0.0610 (12)
H9A	0.3380	0.5543	0.7257	0.073*
H9B	0.4388	0.4763	0.7105	0.073*
C6	0.2391 (3)	−0.2034 (9)	0.4391 (2)	0.0494 (10)
N2	0.3429 (2)	0.2733 (8)	0.64340 (18)	0.0576 (10)
H2A	0.2854	0.2906	0.6265	0.069*
O3	0.4423 (2)	0.3093 (7)	0.84511 (17)	0.0740 (10)
C7	0.2621 (3)	−0.0237 (9)	0.5083 (2)	0.0535 (11)
C1	0.2954 (3)	−0.4110 (9)	0.4191 (2)	0.0555 (11)
H1B	0.3509	−0.4435	0.4501	0.067*
O2	0.3394 (2)	0.0172 (7)	0.7891 (2)	0.0812 (10)
C10	0.3840 (3)	0.2182 (10)	0.7862 (2)	0.0553 (11)
C8	0.3961 (3)	0.1265 (9)	0.6015 (2)	0.0542 (11)
C5	0.1559 (3)	−0.1619 (9)	0.3927 (2)	0.0602 (12)
H5A	0.1168	−0.0250	0.4056	0.072*
C4	0.1308 (3)	−0.3236 (10)	0.3269 (3)	0.0654 (13)
H4A	0.0753	−0.2938	0.2956	0.078*
C3	0.1877 (4)	−0.5258 (11)	0.3085 (3)	0.0704 (14)
H3A	0.1707	−0.6352	0.2647	0.084*
C2	0.2700 (3)	−0.5688 (10)	0.3542 (3)	0.0640 (13)
H2B	0.3088	−0.7062	0.3409	0.077*
C11	0.4497 (4)	0.1530 (13)	0.9180 (3)	0.0918 (19)
H11A	0.4937	0.2362	0.9568	0.138*
H11B	0.4698	−0.0259	0.9074	0.138*
H11C	0.3906	0.1454	0.9381	0.138*

	U11	U22	U33	U12	U13	U23
S1	0.0492 (7)	0.1335 (14)	0.0612 (8)	0.0052 (8)	−0.0012 (5)	−0.0188 (8)
O1	0.0499 (18)	0.093 (3)	0.075 (2)	0.0001 (17)	0.0082 (15)	−0.0248 (19)
N1	0.0436 (19)	0.070 (3)	0.049 (2)	0.0069 (17)	0.0017 (15)	−0.0076 (18)
C9	0.065 (3)	0.059 (3)	0.058 (3)	−0.006 (2)	0.006 (2)	−0.009 (2)
C6	0.049 (2)	0.055 (3)	0.045 (2)	−0.014 (2)	0.0068 (19)	0.003 (2)
N2	0.052 (2)	0.066 (3)	0.054 (2)	0.0030 (19)	−0.0007 (17)	−0.0090 (19)
O3	0.073 (2)	0.095 (3)	0.0531 (18)	−0.0153 (19)	0.0021 (15)	−0.0035 (18)
C7	0.048 (2)	0.058 (3)	0.055 (3)	−0.002 (2)	0.008 (2)	0.002 (2)
C1	0.062 (3)	0.051 (3)	0.054 (3)	−0.004 (2)	0.005 (2)	0.001 (2)
O2	0.092 (2)	0.065 (2)	0.086 (2)	−0.017 (2)	0.0060 (18)	0.0004 (19)
C10	0.051 (3)	0.056 (3)	0.060 (3)	0.001 (2)	0.014 (2)	−0.009 (2)
C8	0.054 (3)	0.062 (3)	0.045 (2)	−0.001 (2)	0.0012 (19)	0.001 (2)
C5	0.058 (3)	0.060 (3)	0.063 (3)	−0.007 (2)	0.008 (2)	−0.003 (2)
C4	0.059 (3)	0.075 (4)	0.059 (3)	−0.016 (3)	−0.006 (2)	0.006 (3)
C3	0.093 (4)	0.063 (3)	0.054 (3)	−0.018 (3)	0.005 (3)	−0.004 (3)
C2	0.080 (3)	0.051 (3)	0.062 (3)	0.000 (2)	0.011 (2)	−0.005 (2)
C11	0.098 (4)	0.123 (5)	0.055 (3)	0.017 (4)	0.008 (3)	0.011 (3)

S1—C8	1.661 (4)	O3—C11	1.452 (5)
O1—C7	1.223 (5)	C1—C2	1.368 (6)
N1—C7	1.371 (5)	C1—H1B	0.93
N1—C8	1.387 (5)	O2—C10	1.197 (5)
N1—H1A	0.86	C5—C4	1.389 (6)
C9—N2	1.437 (5)	C5—H5A	0.93
C9—C10	1.499 (6)	C4—C3	1.361 (6)
C9—H9A	0.97	C4—H4A	0.93
C9—H9B	0.97	C3—C2	1.372 (6)
C6—C1	1.384 (6)	C3—H3A	0.93
C6—C5	1.386 (5)	C2—H2B	0.93
C6—C7	1.482 (6)	C11—H11A	0.96
N2—C8	1.326 (5)	C11—H11B	0.96
N2—H2A	0.86	C11—H11C	0.96
O3—C10	1.318 (5)
C7—N1—C8	129.0 (3)	O2—C10—C9	124.3 (4)
C7—N1—H1A	115.5	O3—C10—C9	111.3 (4)
C8—N1—H1A	115.5	N2—C8—N1	117.4 (4)
N2—C9—C10	112.4 (4)	N2—C8—S1	124.0 (3)
N2—C9—H9A	109.1	N1—C8—S1	118.6 (3)
C10—C9—H9A	109.1	C6—C5—C4	120.4 (4)
N2—C9—H9B	109.1	C6—C5—H5A	119.8
C10—C9—H9B	109.1	C4—C5—H5A	119.8
H9A—C9—H9B	107.9	C3—C4—C5	119.8 (4)
C1—C6—C5	118.6 (4)	C3—C4—H4A	120.1
C1—C6—C7	123.6 (4)	C5—C4—H4A	120.1
C5—C6—C7	117.9 (4)	C4—C3—C2	120.2 (5)
C8—N2—C9	122.3 (4)	C4—C3—H3A	119.9
C8—N2—H2A	118.9	C2—C3—H3A	119.9
C9—N2—H2A	118.9	C1—C2—C3	120.5 (5)
C10—O3—C11	116.2 (4)	C1—C2—H2B	119.8
O1—C7—N1	121.8 (4)	C3—C2—H2B	119.8
O1—C7—C6	122.7 (4)	O3—C11—H11A	109.5
N1—C7—C6	115.5 (4)	O3—C11—H11B	109.5
C2—C1—C6	120.5 (4)	H11A—C11—H11B	109.5
C2—C1—H1B	119.7	O3—C11—H11C	109.5
C6—C1—H1B	119.7	H11A—C11—H11C	109.5
O2—C10—O3	124.4 (4)	H11B—C11—H11C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1	0.86	2.02	2.676 (4)	132
C9—H9B···S1	0.97	2.68	3.027 (4)	101
N1—H1A···S1i	0.86	2.77	3.547 (3)	151
C9—H9A···O2ii	0.97	2.54	3.358 (6)	142
C9—H9A···O2iii	0.97	2.58	3.211 (5)	123

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1	0.86	2.02	2.676 (4)	132
N1—H1A⋯S1i	0.86	2.77	3.547 (3)	151
C9—H9A⋯O2ii	0.97	2.54	3.358 (6)	142
C9—H9A⋯O2iii	0.97	2.58	3.211 (5)	123

Symmetry codes: (i) ; (ii) ; (iii) .