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

The title compound, C(12)H(14)N(2)O(3)S, adopts a cis-trans geometry of the thio-urea group and is stabilized by intra-molecular hydrogen bonds between the carbonyl O atoms and the H atom of the thio-amide group and by a C-H⋯S interaction. Mol-ecules are linked by two inter-molecular hydrogen bonds (C-H⋯O and N-H⋯O), forming a one-dimensional chain parallel to the c axis.

Related literature

For related literature, see: Allen et al. (1987 ▶); Ngah et al. (2005 ▶); Yamin & Hassan (2004 ▶); Yamin & Yusof (2003 ▶).

Experimental

Crystal data

C12H14N2O3S

M = 266.31

Monoclinic,

a = 11.908 (4) Å

b = 7.795 (3) Å

c = 14.024 (5) Å

β = 95.600 (5)°

V = 1295.5 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 298 (2) K

0.46 × 0.36 × 0.22 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.893, T max = 0.947

6762 measured reflections

2537 independent reflections

1967 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.107

S = 1.05

2537 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.23 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/S1600536808024896/at2606sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808024896/at2606Isup2.hkl

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

C12H14N2O3S	F000 = 560
Mr = 266.31	Dx = 1.365 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2409 reflections
a = 11.908 (4) Å	θ = 1.7–26.0º
b = 7.795 (3) Å	µ = 0.25 mm−1
c = 14.024 (5) Å	T = 298 (2) K
β = 95.600 (5)º	Block, colourless
V = 1295.5 (8) Å3	0.46 × 0.36 × 0.22 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	2537 independent reflections
Radiation source: fine-focus sealed tube	1967 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.021
T = 298(2) K	θmax = 26.0º
ω scans	θmin = 1.7º
Absorption correction: multi-scan(SADABS; Bruker, 2000)	h = −14→13
Tmin = 0.893, Tmax = 0.947	k = −9→9
6762 measured reflections	l = −16→17

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)] = 0.041	H-atom parameters constrained
wR(F2) = 0.107	w = 1/[σ2(Fo2) + (0.0476P)2 + 0.3616P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
2537 reflections	Δρmax = 0.20 e Å−3
164 parameters	Δρmin = −0.23 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
S1	0.36516 (4)	0.11910 (9)	0.60927 (4)	0.0632 (2)
O1	0.01958 (11)	0.1765 (2)	0.44591 (9)	0.0615 (4)
O2	0.21706 (12)	0.0629 (2)	0.25554 (10)	0.0657 (4)
O3	0.37578 (11)	−0.0928 (2)	0.25994 (9)	0.0626 (4)
N1	0.15088 (12)	0.2028 (2)	0.57452 (10)	0.0454 (4)
H1	0.1613	0.2428	0.6319	0.055*
N2	0.22969 (13)	0.0690 (2)	0.45050 (11)	0.0506 (4)
H2	0.1650	0.0821	0.4183	0.061*
C1	−0.03537 (15)	0.2974 (3)	0.68490 (13)	0.0482 (5)
H1A	0.0242	0.2412	0.7196	0.058*
C2	−0.11815 (16)	0.3747 (3)	0.73213 (14)	0.0540 (5)
H2A	−0.1145	0.3696	0.7986	0.065*
C3	−0.20575 (16)	0.4590 (3)	0.68161 (15)	0.0545 (5)
H3	−0.2610	0.5118	0.7139	0.065*
C4	−0.21224 (16)	0.4658 (3)	0.58254 (15)	0.0564 (5)
H4	−0.2714	0.5237	0.5483	0.068*
C5	−0.13077 (15)	0.3864 (3)	0.53472 (14)	0.0506 (5)
H5	−0.1361	0.3887	0.4681	0.061*
C6	−0.04087 (14)	0.3032 (2)	0.58545 (12)	0.0417 (4)
C7	0.04366 (15)	0.2218 (3)	0.52873 (13)	0.0455 (4)
C8	0.24393 (15)	0.1270 (2)	0.53931 (13)	0.0438 (4)
C9	0.31818 (16)	−0.0154 (3)	0.40544 (13)	0.0530 (5)
H9A	0.3234	−0.1342	0.4260	0.064*
H9B	0.3898	0.0398	0.4250	0.064*
C10	0.29539 (15)	−0.0079 (3)	0.29841 (13)	0.0477 (5)
C11	0.36926 (19)	−0.1060 (4)	0.15628 (15)	0.0689 (6)
H11A	0.3349	−0.0035	0.1270	0.083*
H11B	0.3236	−0.2041	0.1345	0.083*
C12	0.4835 (2)	−0.1258 (5)	0.1294 (2)	0.1037 (11)
H12A	0.5247	−0.0212	0.1424	0.155*
H12B	0.4808	−0.1518	0.0623	0.155*
H12C	0.5205	−0.2176	0.1658	0.155*

	U11	U22	U33	U12	U13	U23
S1	0.0420 (3)	0.0982 (5)	0.0482 (3)	0.0141 (3)	−0.0011 (2)	−0.0037 (3)
O1	0.0460 (8)	0.0913 (11)	0.0454 (8)	0.0093 (7)	−0.0038 (6)	−0.0176 (7)
O2	0.0519 (8)	0.0904 (12)	0.0549 (8)	0.0172 (8)	0.0059 (7)	0.0103 (8)
O3	0.0517 (8)	0.0912 (11)	0.0451 (8)	0.0174 (8)	0.0064 (6)	−0.0090 (7)
N1	0.0373 (8)	0.0613 (11)	0.0374 (8)	0.0036 (7)	0.0020 (6)	−0.0044 (7)
N2	0.0394 (8)	0.0679 (11)	0.0440 (9)	0.0061 (8)	0.0027 (7)	−0.0091 (8)
C1	0.0392 (9)	0.0605 (13)	0.0441 (10)	0.0027 (9)	−0.0004 (8)	0.0007 (9)
C2	0.0479 (11)	0.0718 (14)	0.0423 (10)	−0.0006 (10)	0.0049 (8)	−0.0038 (10)
C3	0.0431 (10)	0.0649 (14)	0.0567 (12)	0.0026 (10)	0.0109 (9)	−0.0082 (10)
C4	0.0413 (10)	0.0695 (14)	0.0582 (12)	0.0115 (10)	0.0030 (9)	0.0066 (10)
C5	0.0427 (10)	0.0663 (14)	0.0420 (10)	0.0027 (10)	0.0005 (8)	0.0031 (9)
C6	0.0340 (9)	0.0472 (11)	0.0437 (9)	−0.0023 (8)	0.0020 (7)	−0.0009 (8)
C7	0.0403 (9)	0.0530 (12)	0.0425 (10)	−0.0013 (8)	0.0000 (8)	−0.0003 (8)
C8	0.0403 (9)	0.0491 (11)	0.0426 (10)	0.0020 (8)	0.0069 (8)	0.0048 (8)
C9	0.0486 (11)	0.0632 (14)	0.0479 (11)	0.0103 (10)	0.0078 (9)	−0.0017 (10)
C10	0.0407 (10)	0.0548 (12)	0.0480 (10)	−0.0036 (9)	0.0075 (8)	−0.0022 (9)
C11	0.0648 (13)	0.0956 (18)	0.0464 (12)	0.0088 (13)	0.0057 (10)	−0.0100 (12)
C12	0.0712 (17)	0.176 (3)	0.0673 (16)	0.0198 (19)	0.0224 (13)	−0.0087 (19)

S1—C8	1.6656 (19)	C3—C4	1.385 (3)
O1—C7	1.221 (2)	C3—H3	0.9300
O2—C10	1.194 (2)	C4—C5	1.379 (3)
O3—C10	1.322 (2)	C4—H4	0.9300
O3—C11	1.452 (2)	C5—C6	1.387 (3)
N1—C7	1.380 (2)	C5—H5	0.9300
N1—C8	1.388 (2)	C6—C7	1.485 (3)
N1—H1	0.8600	C9—C10	1.500 (3)
N2—C8	1.320 (2)	C9—H9A	0.9700
N2—C9	1.439 (2)	C9—H9B	0.9700
N2—H2	0.8600	C11—C12	1.455 (3)
C1—C2	1.379 (3)	C11—H11A	0.9700
C1—C6	1.390 (2)	C11—H11B	0.9700
C1—H1A	0.9300	C12—H12A	0.9600
C2—C3	1.370 (3)	C12—H12B	0.9600
C2—H2A	0.9300	C12—H12C	0.9600
C10—O3—C11	118.29 (16)	O1—C7—C6	121.65 (16)
C7—N1—C8	127.91 (15)	N1—C7—C6	116.19 (15)
C7—N1—H1	116.0	N2—C8—N1	116.61 (15)
C8—N1—H1	116.0	N2—C8—S1	124.54 (14)
C8—N2—C9	122.58 (15)	N1—C8—S1	118.83 (14)
C8—N2—H2	118.7	N2—C9—C10	110.66 (16)
C9—N2—H2	118.7	N2—C9—H9A	109.5
C2—C1—C6	120.11 (17)	C10—C9—H9A	109.5
C2—C1—H1A	119.9	N2—C9—H9B	109.5
C6—C1—H1A	119.9	C10—C9—H9B	109.5
C3—C2—C1	120.33 (18)	H9A—C9—H9B	108.1
C3—C2—H2A	119.8	O2—C10—O3	125.96 (18)
C1—C2—H2A	119.8	O2—C10—C9	125.28 (18)
C2—C3—C4	120.14 (18)	O3—C10—C9	108.75 (16)
C2—C3—H3	119.9	O3—C11—C12	107.9 (2)
C4—C3—H3	119.9	O3—C11—H11A	110.1
C5—C4—C3	119.86 (18)	C12—C11—H11A	110.1
C5—C4—H4	120.1	O3—C11—H11B	110.1
C3—C4—H4	120.1	C12—C11—H11B	110.1
C4—C5—C6	120.32 (18)	H11A—C11—H11B	108.4
C4—C5—H5	119.8	C11—C12—H12A	109.5
C6—C5—H5	119.8	C11—C12—H12B	109.5
C5—C6—C1	119.22 (17)	H12A—C12—H12B	109.5
C5—C6—C7	117.04 (16)	C11—C12—H12C	109.5
C1—C6—C7	123.72 (16)	H12A—C12—H12C	109.5
O1—C7—N1	122.16 (17)	H12B—C12—H12C	109.5
C6—C1—C2—C3	−0.6 (3)	C5—C6—C7—N1	154.41 (18)
C1—C2—C3—C4	0.6 (3)	C1—C6—C7—N1	−26.8 (3)
C2—C3—C4—C5	0.5 (3)	C9—N2—C8—N1	−178.79 (17)
C3—C4—C5—C6	−1.5 (3)	C9—N2—C8—S1	2.7 (3)
C4—C5—C6—C1	1.5 (3)	C7—N1—C8—N2	1.6 (3)
C4—C5—C6—C7	−179.66 (19)	C7—N1—C8—S1	−179.77 (16)
C2—C1—C6—C5	−0.5 (3)	C8—N2—C9—C10	−158.69 (18)
C2—C1—C6—C7	−179.21 (19)	C11—O3—C10—O2	−1.2 (3)
C8—N1—C7—O1	−3.0 (3)	C11—O3—C10—C9	178.55 (19)
C8—N1—C7—C6	177.93 (17)	N2—C9—C10—O2	2.4 (3)
C5—C6—C7—O1	−24.7 (3)	N2—C9—C10—O3	−177.34 (17)
C1—C6—C7—O1	154.1 (2)	C10—O3—C11—C12	153.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.86	1.95	2.633 (2)	135
N2—H2···O2	0.86	2.43	2.724 (2)	101
C9—H9B···S1	0.97	2.70	3.045 (2)	101
N1—H1···O2i	0.86	2.35	3.164 (2)	158
C2—H2A···O1i	0.93	2.51	3.298 (3)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1	0.86	1.95	2.633 (2)	135
N2—H2⋯O2	0.86	2.43	2.724 (2)	101
C9—H9B⋯S1	0.97	2.70	3.045 (2)	101
N1—H1⋯O2i	0.86	2.35	3.164 (2)	158
C2—H2A⋯O1i	0.93	2.51	3.298 (3)	143

Symmetry code: (i) .