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

The title compound, C(13)H(16)N(2)O(3)S, is a thio-urea derivative with benzoyl and propoxycarbonyl-methyl groups attached to the two terminal N atoms. These groups adopt trans and cis configurations, respectively, with respect to the S atom across the thio-urea C-N bonds. The compound crystallizes in the P2(1)/c space group with Z = 8, resulting in two unique molecules in the asymmetric unit linked by C-H⋯S and C-H⋯O hydrogen bonds, forming a one-dimensional zigzag chain along the c axis.

Related literature

For information on bond lengths and angles, see: Allen et al. (1987 ▶). For related literature on an analogous molecule, see: Hassan et al. (2008 ▶). For related structures, see: Yamin & Hassan (2004 ▶); Yamin & Yusof (2003 ▶).

Experimental

Crystal data

C13H16N2O3S

M = 280.34

Monoclinic,

a = 11.6722 (19) Å

b = 15.105 (3) Å

c = 16.584 (3) Å

β = 104.737 (3)°

V = 2827.6 (8) Å3

Z = 8

Mo Kα radiation

μ = 0.23 mm−1

T = 298 (2) K

0.34 × 0.29 × 0.09 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.925, T max = 0.979

15002 measured reflections

5262 independent reflections

2854 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.162

S = 1.05

5262 reflections

359 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.17 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/S1600536808030596/at2635sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808030596/at2635Isup2.hkl

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

C13H16N2O3S	F(000) = 1184
Mr = 280.34	Dx = 1.317 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1848 reflections
a = 11.6722 (19) Å	θ = 1.8–25.5°
b = 15.105 (3) Å	µ = 0.23 mm−1
c = 16.584 (3) Å	T = 298 K
β = 104.737 (3)°	Block, yellowish
V = 2827.6 (8) Å3	0.34 × 0.29 × 0.09 mm
Z = 8

Bruker SMART APEX CCD area-detector diffractometer	5262 independent reflections
Radiation source: fine-focus sealed tube	2854 reflections with I > 2σ(I)
graphite	Rint = 0.045
ω scans	θmax = 25.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −14→14
Tmin = 0.925, Tmax = 0.979	k = −14→18
15002 measured reflections	l = −19→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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.162	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0665P)2 + 0.3497P] where P = (Fo2 + 2Fc2)/3
5262 reflections	(Δ/σ)max < 0.001
359 parameters	Δρmax = 0.21 e Å−3
4 restraints	Δρmin = −0.17 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
C1	−0.1076 (3)	0.8544 (3)	0.0140 (2)	0.0722 (11)
H1A	−0.1024	0.8130	−0.0264	0.087*
C2	−0.2152 (3)	0.8706 (3)	0.0310 (3)	0.0848 (13)
H2A	−0.2822	0.8397	0.0024	0.102*
C3	−0.2240 (3)	0.9320 (3)	0.0899 (3)	0.0768 (12)
H3A	−0.2962	0.9418	0.1024	0.092*
C4	−0.1257 (3)	0.9787 (3)	0.1302 (2)	0.0693 (11)
H4A	−0.1319	1.0215	0.1692	0.083*
C5	−0.0180 (3)	0.9630 (2)	0.1138 (2)	0.0574 (9)
H5A	0.0481	0.9954	0.1413	0.069*
C6	−0.0074 (3)	0.8993 (2)	0.05653 (19)	0.0496 (8)
C7	0.1050 (3)	0.8780 (2)	0.0338 (2)	0.0497 (8)
C8	0.3228 (3)	0.9015 (2)	0.0755 (2)	0.0516 (8)
C9	0.4434 (3)	0.8520 (2)	−0.01556 (19)	0.0613 (10)
H9A	0.4869	0.8037	0.0170	0.074*
H9B	0.4912	0.9052	−0.0031	0.074*
C10	0.4199 (3)	0.8311 (2)	−0.1062 (2)	0.0587 (9)
C11	0.5118 (3)	0.7963 (3)	−0.2139 (2)	0.0736 (11)
H11A	0.4604	0.8405	−0.2472	0.088*
H11B	0.4796	0.7382	−0.2314	0.088*
C12	0.6336 (4)	0.8042 (3)	−0.2255 (2)	0.0941 (14)
H12A	0.6655	0.8618	−0.2060	0.113*
H12B	0.6838	0.7596	−0.1919	0.113*
C13	0.6363 (4)	0.7930 (4)	−0.3139 (3)	0.1222 (19)
H13A	0.7164	0.7981	−0.3184	0.183*
H13B	0.5885	0.8381	−0.3472	0.183*
H13C	0.6056	0.7358	−0.3333	0.183*
C14	0.6343 (3)	0.9685 (2)	0.3361 (2)	0.0616 (9)
H14A	0.5673	0.9970	0.3044	0.074*
C15	0.7394 (3)	0.9753 (3)	0.3139 (2)	0.0733 (11)
H15A	0.7429	1.0078	0.2670	0.088*
C16	0.8391 (3)	0.9346 (3)	0.3604 (3)	0.0784 (12)
H16A	0.9099	0.9380	0.3446	0.094*
C17	0.8334 (3)	0.8889 (3)	0.4306 (3)	0.0912 (13)
H17A	0.9013	0.8626	0.4636	0.109*
C18	0.7284 (3)	0.8816 (3)	0.4524 (2)	0.0773 (12)
H18A	0.7256	0.8504	0.5002	0.093*
C19	0.6270 (3)	0.9199 (2)	0.40472 (19)	0.0505 (8)
C20	0.5155 (3)	0.9068 (2)	0.4304 (2)	0.0577 (9)
C21	0.2955 (3)	0.9159 (2)	0.3802 (2)	0.0533 (9)
C22	0.1736 (3)	0.8807 (2)	0.4749 (2)	0.0619 (10)
H22A	0.1218	0.8419	0.4352	0.074*
H22B	0.1356	0.9381	0.4727	0.074*
C23	0.1951 (3)	0.8429 (2)	0.5608 (2)	0.0577 (9)
C24	0.1014 (3)	0.8073 (3)	0.66818 (19)	0.0659 (10)
H24A	0.1632	0.8375	0.7091	0.079*
H24B	0.1196	0.7445	0.6705	0.079*
C25	−0.0153 (3)	0.8223 (3)	0.6859 (2)	0.0830 (12)
H25A	−0.0768	0.7951	0.6424	0.100*
H25B	−0.0310	0.8854	0.6855	0.100*
C26	−0.0200 (4)	0.7843 (3)	0.7694 (2)	0.1020 (15)
H26A	−0.0966	0.7953	0.7787	0.153*
H26B	0.0397	0.8119	0.8128	0.153*
H26C	−0.0060	0.7217	0.7697	0.153*
S1	0.43593 (8)	0.94060 (8)	0.14867 (6)	0.0800 (4)
S2	0.18284 (8)	0.94066 (8)	0.30082 (6)	0.0798 (4)
O1	0.10454 (18)	0.83491 (16)	−0.02851 (14)	0.0655 (7)
O2	0.3254 (2)	0.8365 (2)	−0.15350 (16)	0.1033 (11)
O3	0.51810 (19)	0.80959 (16)	−0.12641 (13)	0.0662 (7)
O4	0.5165 (2)	0.88349 (19)	0.50080 (15)	0.0841 (9)
O5	0.2888 (2)	0.81729 (17)	0.60138 (14)	0.0708 (7)
O6	0.09492 (18)	0.84165 (16)	0.58525 (13)	0.0653 (7)
N1	0.2084 (2)	0.90800 (19)	0.08632 (17)	0.0533 (7)
N2	0.3327 (2)	0.8649 (2)	0.00618 (17)	0.0571 (8)
N3	0.4114 (2)	0.92075 (19)	0.37143 (16)	0.0533 (7)
N4	0.2860 (2)	0.8897 (2)	0.45399 (18)	0.0600 (8)
H3B	0.416 (3)	0.935 (2)	0.3220 (10)	0.074 (12)*
H2B	0.2684 (17)	0.847 (2)	−0.0292 (16)	0.070 (12)*
H1B	0.206 (3)	0.9362 (19)	0.1312 (13)	0.069 (11)*
H4B	0.346 (2)	0.870 (3)	0.4919 (18)	0.105 (16)*

	U11	U22	U33	U12	U13	U23
C1	0.051 (2)	0.085 (3)	0.079 (3)	0.003 (2)	0.014 (2)	−0.016 (2)
C2	0.041 (2)	0.104 (4)	0.107 (3)	−0.006 (2)	0.015 (2)	−0.014 (3)
C3	0.049 (2)	0.100 (3)	0.085 (3)	0.008 (2)	0.026 (2)	0.005 (3)
C4	0.056 (2)	0.096 (3)	0.061 (2)	0.004 (2)	0.0243 (19)	−0.002 (2)
C5	0.049 (2)	0.073 (3)	0.051 (2)	0.0037 (18)	0.0134 (16)	0.0041 (18)
C6	0.0412 (19)	0.059 (2)	0.048 (2)	0.0043 (17)	0.0091 (16)	0.0127 (17)
C7	0.046 (2)	0.058 (2)	0.044 (2)	0.0019 (17)	0.0083 (17)	0.0041 (17)
C8	0.0446 (19)	0.061 (2)	0.051 (2)	0.0042 (16)	0.0159 (16)	0.0015 (17)
C9	0.047 (2)	0.085 (3)	0.053 (2)	0.0110 (19)	0.0149 (17)	−0.0033 (18)
C10	0.053 (2)	0.073 (3)	0.050 (2)	0.010 (2)	0.0144 (19)	0.0010 (18)
C11	0.075 (3)	0.101 (3)	0.048 (2)	0.008 (2)	0.0221 (19)	0.001 (2)
C12	0.081 (3)	0.145 (4)	0.064 (3)	0.015 (3)	0.033 (2)	0.000 (2)
C13	0.102 (4)	0.199 (6)	0.075 (3)	−0.003 (4)	0.038 (3)	0.000 (3)
C14	0.051 (2)	0.081 (3)	0.049 (2)	−0.0051 (19)	0.0066 (17)	0.0075 (19)
C15	0.062 (2)	0.103 (3)	0.059 (2)	−0.019 (2)	0.023 (2)	0.001 (2)
C16	0.054 (2)	0.097 (3)	0.091 (3)	−0.007 (2)	0.031 (2)	−0.009 (3)
C17	0.051 (2)	0.111 (4)	0.107 (4)	0.010 (2)	0.010 (2)	0.030 (3)
C18	0.048 (2)	0.100 (3)	0.080 (3)	0.005 (2)	0.009 (2)	0.029 (2)
C19	0.0401 (18)	0.062 (2)	0.048 (2)	−0.0049 (17)	0.0094 (16)	−0.0031 (17)
C20	0.053 (2)	0.072 (3)	0.048 (2)	−0.0006 (18)	0.0109 (18)	0.0033 (18)
C21	0.0461 (19)	0.066 (2)	0.048 (2)	0.0012 (17)	0.0133 (16)	−0.0017 (17)
C22	0.0465 (19)	0.087 (3)	0.054 (2)	−0.0023 (19)	0.0160 (17)	0.0005 (19)
C23	0.050 (2)	0.073 (3)	0.052 (2)	−0.006 (2)	0.0149 (19)	−0.0118 (18)
C24	0.064 (2)	0.091 (3)	0.045 (2)	−0.007 (2)	0.0166 (18)	0.0012 (19)
C25	0.068 (3)	0.125 (4)	0.063 (3)	0.006 (2)	0.028 (2)	0.004 (2)
C26	0.099 (3)	0.152 (4)	0.065 (3)	−0.006 (3)	0.040 (2)	0.009 (3)
S1	0.0493 (5)	0.1229 (10)	0.0681 (7)	−0.0131 (6)	0.0158 (5)	−0.0340 (6)
S2	0.0485 (5)	0.1340 (10)	0.0562 (6)	0.0120 (6)	0.0123 (5)	0.0196 (6)
O1	0.0526 (14)	0.0873 (19)	0.0552 (15)	0.0002 (13)	0.0114 (12)	−0.0157 (13)
O2	0.0507 (16)	0.198 (3)	0.0565 (17)	0.0217 (19)	0.0055 (14)	−0.0217 (18)
O3	0.0530 (14)	0.100 (2)	0.0487 (15)	0.0152 (13)	0.0182 (11)	−0.0011 (12)
O4	0.0499 (15)	0.149 (3)	0.0520 (16)	−0.0021 (15)	0.0104 (12)	0.0278 (16)
O5	0.0522 (15)	0.102 (2)	0.0575 (16)	0.0037 (14)	0.0133 (12)	0.0067 (13)
O6	0.0513 (14)	0.100 (2)	0.0476 (14)	−0.0055 (13)	0.0177 (11)	0.0008 (12)
N1	0.0449 (16)	0.071 (2)	0.0453 (18)	0.0000 (15)	0.0131 (14)	−0.0076 (15)
N2	0.0401 (17)	0.085 (2)	0.0465 (18)	0.0048 (16)	0.0106 (15)	−0.0061 (15)
N3	0.0414 (16)	0.077 (2)	0.0415 (17)	0.0009 (14)	0.0106 (14)	0.0073 (15)
N4	0.0470 (17)	0.090 (2)	0.0461 (18)	−0.0001 (17)	0.0174 (15)	0.0069 (16)

C1—C2	1.378 (5)	C14—H14A	0.9300
C1—C6	1.380 (4)	C15—C16	1.367 (5)
C1—H1A	0.9300	C15—H15A	0.9300
C2—C3	1.368 (5)	C16—C17	1.370 (5)
C2—H2A	0.9300	C16—H16A	0.9300
C3—C4	1.368 (5)	C17—C18	1.368 (5)
C3—H3A	0.9300	C17—H17A	0.9300
C4—C5	1.373 (4)	C18—C19	1.373 (4)
C4—H4A	0.9300	C18—H18A	0.9300
C5—C6	1.378 (4)	C19—C20	1.482 (4)
C5—H5A	0.9300	C20—O4	1.217 (4)
C6—C7	1.490 (4)	C20—N3	1.369 (4)
C7—O1	1.220 (3)	C21—N4	1.317 (4)
C7—N1	1.373 (4)	C21—N3	1.399 (4)
C8—N2	1.307 (4)	C21—S2	1.649 (3)
C8—N1	1.395 (4)	C22—N4	1.446 (4)
C8—S1	1.658 (3)	C22—C23	1.496 (4)
C9—N2	1.440 (4)	C22—H22A	0.9700
C9—C10	1.492 (4)	C22—H22B	0.9700
C9—H9A	0.9700	C23—O5	1.193 (4)
C9—H9B	0.9700	C23—O6	1.332 (4)
C10—O2	1.182 (4)	C24—O6	1.454 (4)
C10—O3	1.314 (4)	C24—C25	1.483 (4)
C11—O3	1.447 (4)	C24—H24A	0.9700
C11—C12	1.487 (5)	C24—H24B	0.9700
C11—H11A	0.9700	C25—C26	1.512 (5)
C11—H11B	0.9700	C25—H25A	0.9700
C12—C13	1.484 (5)	C25—H25B	0.9700
C12—H12A	0.9700	C26—H26A	0.9600
C12—H12B	0.9700	C26—H26B	0.9600
C13—H13A	0.9600	C26—H26C	0.9600
C13—H13B	0.9600	N1—H1B	0.863 (10)
C13—H13C	0.9600	N2—H2B	0.871 (10)
C14—C15	1.371 (4)	N3—H3B	0.862 (10)
C14—C19	1.375 (4)	N4—H4B	0.867 (10)
C2—C1—C6	120.4 (4)	C15—C16—H16A	120.4
C2—C1—H1A	119.8	C17—C16—H16A	120.4
C6—C1—H1A	119.8	C18—C17—C16	120.4 (4)
C3—C2—C1	120.3 (4)	C18—C17—H17A	119.8
C3—C2—H2A	119.9	C16—C17—H17A	119.8
C1—C2—H2A	119.9	C17—C18—C19	120.8 (4)
C4—C3—C2	119.5 (3)	C17—C18—H18A	119.6
C4—C3—H3A	120.2	C19—C18—H18A	119.6
C2—C3—H3A	120.2	C18—C19—C14	118.4 (3)
C3—C4—C5	120.6 (4)	C18—C19—C20	118.0 (3)
C3—C4—H4A	119.7	C14—C19—C20	123.6 (3)
C5—C4—H4A	119.7	O4—C20—N3	121.3 (3)
C4—C5—C6	120.3 (3)	O4—C20—C19	121.3 (3)
C4—C5—H5A	119.9	N3—C20—C19	117.3 (3)
C6—C5—H5A	119.9	N4—C21—N3	115.1 (3)
C5—C6—C1	118.8 (3)	N4—C21—S2	124.8 (2)
C5—C6—C7	124.3 (3)	N3—C21—S2	120.0 (2)
C1—C6—C7	116.8 (3)	N4—C22—C23	108.8 (3)
O1—C7—N1	121.8 (3)	N4—C22—H22A	109.9
O1—C7—C6	121.0 (3)	C23—C22—H22A	109.9
N1—C7—C6	117.2 (3)	N4—C22—H22B	109.9
N2—C8—N1	116.4 (3)	C23—C22—H22B	109.9
N2—C8—S1	124.2 (2)	H22A—C22—H22B	108.3
N1—C8—S1	119.4 (2)	O5—C23—O6	125.0 (3)
N2—C9—C10	109.5 (3)	O5—C23—C22	124.6 (3)
N2—C9—H9A	109.8	O6—C23—C22	110.4 (3)
C10—C9—H9A	109.8	O6—C24—C25	107.7 (3)
N2—C9—H9B	109.8	O6—C24—H24A	110.2
C10—C9—H9B	109.8	C25—C24—H24A	110.2
H9A—C9—H9B	108.2	O6—C24—H24B	110.2
O2—C10—O3	125.1 (3)	C25—C24—H24B	110.2
O2—C10—C9	123.7 (3)	H24A—C24—H24B	108.5
O3—C10—C9	111.1 (3)	C24—C25—C26	111.9 (3)
O3—C11—C12	108.2 (3)	C24—C25—H25A	109.2
O3—C11—H11A	110.1	C26—C25—H25A	109.2
C12—C11—H11A	110.1	C24—C25—H25B	109.2
O3—C11—H11B	110.1	C26—C25—H25B	109.2
C12—C11—H11B	110.1	H25A—C25—H25B	107.9
H11A—C11—H11B	108.4	C25—C26—H26A	109.5
C13—C12—C11	112.4 (4)	C25—C26—H26B	109.5
C13—C12—H12A	109.1	H26A—C26—H26B	109.5
C11—C12—H12A	109.1	C25—C26—H26C	109.5
C13—C12—H12B	109.1	H26A—C26—H26C	109.5
C11—C12—H12B	109.1	H26B—C26—H26C	109.5
H12A—C12—H12B	107.9	C10—O3—C11	117.6 (3)
C12—C13—H13A	109.5	C23—O6—C24	117.0 (3)
C12—C13—H13B	109.5	C7—N1—C8	127.7 (3)
H13A—C13—H13B	109.5	C7—N1—H1B	120 (2)
C12—C13—H13C	109.5	C8—N1—H1B	112 (2)
H13A—C13—H13C	109.5	C8—N2—C9	124.3 (3)
H13B—C13—H13C	109.5	C8—N2—H2B	118 (2)
C15—C14—C19	120.7 (3)	C9—N2—H2B	118 (2)
C15—C14—H14A	119.7	C20—N3—C21	128.6 (3)
C19—C14—H14A	119.7	C20—N3—H3B	117 (2)
C16—C15—C14	120.4 (4)	C21—N3—H3B	114 (2)
C16—C15—H15A	119.8	C21—N4—C22	123.1 (3)
C14—C15—H15A	119.8	C21—N4—H4B	122 (3)
C15—C16—C17	119.2 (3)	C22—N4—H4B	114 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O1	0.87 (2)	1.92 (2)	2.617 (3)	136 (2)
N2—H2B···O2	0.87 (2)	2.33 (2)	2.663 (4)	103 (2)
N4—H4B···O4	0.87 (3)	1.97 (2)	2.605 (4)	129 (3)
N4—H4B···O5	0.87 (3)	2.23 (3)	2.671 (4)	111 (2)
C5—H5A···S2	0.93	2.84	3.396 (3)	120
C13—H13B···O4i	0.96	2.54	3.329 (6)	139
C14—H14A···S1	0.93	2.78	3.397 (3)	125
C24—H24A···O2ii	0.97	2.57	3.441 (4)	150
C26—H26B···O1ii	0.96	2.57	3.384 (4)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯O1	0.87 (2)	1.92 (2)	2.617 (3)	136 (2)
N2—H2B⋯O2	0.87 (2)	2.33 (2)	2.663 (4)	103.1 (17)
N4—H4B⋯O4	0.87 (3)	1.97 (2)	2.605 (4)	129 (3)
N4—H4B⋯O5	0.87 (3)	2.23 (3)	2.671 (4)	111 (2)
C5—H5A⋯S2	0.93	2.84	3.396 (3)	120
C13—H13B⋯O4i	0.96	2.54	3.329 (6)	139
C14—H14A⋯S1	0.93	2.78	3.397 (3)	125
C24—H24A⋯O2ii	0.97	2.57	3.441 (4)	150
C26—H26B⋯O1ii	0.96	2.57	3.384 (4)	143

Symmetry codes: (i) ; (ii) .