Methyl 3-(3-benzoyl-thio-ureido)propano-ate.

In the title compound, C(12)H(14)N(2)O(3)S, the propyl acetate group and the benzoyl group adopt a cis-trans conformation, respectively, with respect to the thiono S atom across the C-N bonds. The phenyl ring is twisted relative to the the thio-urea mean plane, forming a dihedral angle of 24.16 (9)°. An intra-molecular N-H⋯O hydrogen bond occurs. The crystal packing is stabilized by inter-molecular N-H⋯O and C-H⋯O hydrogen bonds, forming a chain along the a axis.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For related strutures, see: Yamin & Hassan (2004 ▶); Hassan et al. (2008a ▶,b ▶,c ▶, 2009 ▶), Hung et al. (2010 ▶). For a related synthesis, see: Hassan et al. (2008

Experimental

Crystal data

C12H14N2O3S

M = 266.31

Triclinic,

a = 7.5901 (18) Å

b = 8.2688 (19) Å

c = 10.547 (3) Å

α = 86.168 (5)°

β = 86.892 (4)°

γ = 81.545 (4)°

V = 652.6 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.25 mm−1

T = 298 K

0.35 × 0.31 × 0.23 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.918, T max = 0.945

8953 measured reflections

3229 independent reflections

2654 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.141

S = 1.12

3229 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.27 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: ORTEPIII (Burnett & Johnson, 1996 ▶), ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶), PARST (Nardelli, 1995 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681100568X/dn2657sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681100568X/dn2657Isup2.hkl

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

C12H14N2O3S	Z = 2
Mr = 266.31	F(000) = 280
Triclinic, P1	Dx = 1.355 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5901 (18) Å	Cell parameters from 2861 reflections
b = 8.2688 (19) Å	θ = 1.9–28.3°
c = 10.547 (3) Å	µ = 0.25 mm−1
α = 86.168 (5)°	T = 298 K
β = 86.892 (4)°	Block, colourless
γ = 81.545 (4)°	0.35 × 0.31 × 0.23 mm
V = 652.6 (3) Å3

Bruker SMART APEX CCD area-detector diffractometer	3229 independent reflections
Radiation source: fine-focus sealed tube	2654 reflections with I > 2σ(I)
graphite	Rint = 0.024
ω scans	θmax = 28.3°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −10→10
Tmin = 0.918, Tmax = 0.945	k = −11→11
8953 measured reflections	l = −14→14

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141	H-atom parameters constrained
S = 1.12	w = 1/[σ2(Fo2) + (0.0624P)2 + 0.1657P] where P = (Fo2 + 2Fc2)/3
3229 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.22 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	0.38506 (7)	0.35748 (7)	0.87738 (5)	0.05290 (19)
O1	0.2339 (2)	0.3507 (2)	0.46757 (14)	0.0658 (5)
O2	−0.1984 (2)	0.2418 (2)	0.71396 (14)	0.0594 (4)
O3	−0.1813 (2)	0.1042 (2)	0.90333 (16)	0.0656 (5)
N1	0.4213 (2)	0.3096 (2)	0.63147 (15)	0.0442 (4)
H1A	0.5305	0.2778	0.6496	0.053*
N2	0.1375 (2)	0.4127 (2)	0.70422 (15)	0.0472 (4)
H2A	0.1086	0.4052	0.6273	0.057*
C1	0.6740 (3)	0.1203 (3)	0.4582 (2)	0.0572 (6)
H1B	0.6873	0.0919	0.5444	0.069*
C2	0.7984 (3)	0.0513 (3)	0.3688 (3)	0.0685 (7)
H2B	0.8948	−0.0242	0.3949	0.082*
C3	0.7794 (3)	0.0944 (3)	0.2416 (2)	0.0644 (6)
H3A	0.8635	0.0484	0.1820	0.077*
C4	0.6379 (3)	0.2044 (3)	0.2022 (2)	0.0630 (6)
H4A	0.6256	0.2331	0.1160	0.076*
C5	0.5136 (3)	0.2726 (3)	0.2903 (2)	0.0544 (5)
H5A	0.4173	0.3473	0.2630	0.065*
C6	0.5295 (3)	0.2318 (2)	0.41872 (18)	0.0429 (4)
C7	0.3820 (3)	0.3027 (3)	0.50660 (18)	0.0457 (5)
C8	0.3050 (3)	0.3619 (2)	0.73260 (17)	0.0412 (4)
C9	−0.0010 (3)	0.4804 (3)	0.7945 (2)	0.0524 (5)
H9A	−0.0993	0.5396	0.7477	0.063*
H9B	0.0463	0.5584	0.8432	0.063*
C10	−0.0714 (3)	0.3532 (3)	0.88575 (19)	0.0548 (6)
H10A	0.0264	0.2960	0.9341	0.066*
H10B	−0.1579	0.4087	0.9453	0.066*
C11	−0.1567 (2)	0.2306 (3)	0.82278 (19)	0.0498 (5)
C12	−0.2732 (4)	−0.0183 (4)	0.8564 (3)	0.0828 (8)
H12A	−0.2834	−0.1032	0.9219	0.124*
H12B	−0.2074	−0.0642	0.7838	0.124*
H12C	−0.3900	0.0309	0.8323	0.124*

	U11	U22	U33	U12	U13	U23
S1	0.0462 (3)	0.0734 (4)	0.0374 (3)	0.0019 (2)	−0.0064 (2)	−0.0099 (2)
O1	0.0455 (8)	0.1087 (14)	0.0376 (8)	0.0111 (8)	−0.0050 (6)	−0.0092 (8)
O2	0.0487 (9)	0.0918 (12)	0.0405 (8)	−0.0169 (8)	−0.0049 (6)	−0.0074 (8)
O3	0.0587 (10)	0.0788 (12)	0.0545 (9)	0.0018 (8)	−0.0010 (8)	0.0032 (8)
N1	0.0347 (8)	0.0593 (10)	0.0377 (8)	−0.0015 (7)	−0.0020 (6)	−0.0076 (7)
N2	0.0380 (8)	0.0664 (11)	0.0360 (8)	−0.0001 (8)	−0.0033 (6)	−0.0086 (7)
C1	0.0571 (13)	0.0664 (14)	0.0464 (11)	0.0019 (11)	−0.0066 (10)	−0.0101 (10)
C2	0.0546 (14)	0.0803 (17)	0.0663 (15)	0.0120 (12)	−0.0043 (11)	−0.0194 (13)
C3	0.0532 (13)	0.0839 (17)	0.0544 (13)	−0.0035 (12)	0.0137 (10)	−0.0200 (12)
C4	0.0623 (14)	0.0824 (17)	0.0419 (11)	−0.0071 (12)	0.0108 (10)	−0.0037 (11)
C5	0.0491 (12)	0.0660 (14)	0.0450 (11)	−0.0022 (10)	0.0038 (9)	0.0005 (10)
C6	0.0407 (10)	0.0494 (11)	0.0400 (10)	−0.0096 (8)	0.0009 (8)	−0.0072 (8)
C7	0.0434 (10)	0.0571 (12)	0.0362 (9)	−0.0061 (9)	−0.0008 (8)	−0.0039 (8)
C8	0.0406 (10)	0.0456 (10)	0.0369 (9)	−0.0042 (8)	−0.0007 (7)	−0.0043 (8)
C9	0.0415 (10)	0.0669 (14)	0.0467 (11)	0.0063 (9)	−0.0034 (9)	−0.0172 (10)
C10	0.0410 (10)	0.0857 (16)	0.0365 (10)	−0.0008 (10)	0.0006 (8)	−0.0160 (10)
C11	0.0300 (9)	0.0757 (14)	0.0398 (10)	0.0046 (9)	0.0044 (8)	−0.0075 (10)
C12	0.0768 (19)	0.0713 (18)	0.098 (2)	−0.0117 (15)	0.0022 (16)	0.0070 (16)

S1—C8	1.6699 (19)	C3—C4	1.365 (4)
O1—C7	1.220 (2)	C3—H3A	0.9300
O2—C11	1.201 (2)	C4—C5	1.375 (3)
O3—C11	1.331 (3)	C4—H4A	0.9300
O3—C12	1.438 (3)	C5—C6	1.381 (3)
N1—C7	1.373 (2)	C5—H5A	0.9300
N1—C8	1.397 (2)	C6—C7	1.491 (3)
N1—H1A	0.8600	C9—C10	1.514 (3)
N2—C8	1.323 (2)	C9—H9A	0.9700
N2—C9	1.454 (2)	C9—H9B	0.9700
N2—H2A	0.8600	C10—C11	1.489 (3)
C1—C2	1.387 (3)	C10—H10A	0.9700
C1—C6	1.388 (3)	C10—H10B	0.9700
C1—H1B	0.9300	C12—H12A	0.9600
C2—C3	1.375 (4)	C12—H12B	0.9600
C2—H2B	0.9300	C12—H12C	0.9600
C11—O3—C12	116.5 (2)	O1—C7—C6	120.56 (18)
C7—N1—C8	127.78 (16)	N1—C7—C6	116.94 (17)
C7—N1—H1A	116.1	N2—C8—N1	116.04 (16)
C8—N1—H1A	116.1	N2—C8—S1	125.16 (15)
C8—N2—C9	124.28 (16)	N1—C8—S1	118.80 (14)
C8—N2—H2A	117.9	N2—C9—C10	113.98 (18)
C9—N2—H2A	117.9	N2—C9—H9A	108.8
C2—C1—C6	119.8 (2)	C10—C9—H9A	108.8
C2—C1—H1B	120.1	N2—C9—H9B	108.8
C6—C1—H1B	120.1	C10—C9—H9B	108.8
C3—C2—C1	120.0 (2)	H9A—C9—H9B	107.7
C3—C2—H2B	120.0	C11—C10—C9	114.09 (17)
C1—C2—H2B	120.0	C11—C10—H10A	108.7
C4—C3—C2	120.5 (2)	C9—C10—H10A	108.7
C4—C3—H3A	119.8	C11—C10—H10B	108.7
C2—C3—H3A	119.8	C9—C10—H10B	108.7
C3—C4—C5	119.8 (2)	H10A—C10—H10B	107.6
C3—C4—H4A	120.1	O2—C11—O3	123.6 (2)
C5—C4—H4A	120.1	O2—C11—C10	125.4 (2)
C4—C5—C6	121.0 (2)	O3—C11—C10	110.98 (18)
C4—C5—H5A	119.5	O3—C12—H12A	109.5
C6—C5—H5A	119.5	O3—C12—H12B	109.5
C5—C6—C1	118.93 (19)	H12A—C12—H12B	109.5
C5—C6—C7	117.30 (18)	O3—C12—H12C	109.5
C1—C6—C7	123.63 (18)	H12A—C12—H12C	109.5
O1—C7—N1	122.51 (18)	H12B—C12—H12C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1	0.86	1.94	2.625 (2)	136
N1—H1A···O2i	0.86	2.17	3.022 (2)	169
C1—H1B···O2i	0.93	2.50	3.187 (3)	130
C9—H9A···O1ii	0.97	2.59	3.464 (3)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1	0.86	1.94	2.625 (2)	136
N1—H1A⋯O2i	0.86	2.17	3.022 (2)	169
C1—H1B⋯O2i	0.93	2.50	3.187 (3)	130
C9—H9A⋯O1ii	0.97	2.59	3.464 (3)	150

Symmetry codes: (i) ; (ii) .