(E)-2-(3-Cinnamoyl-thio-ureido)acetic acid dimethyl sulfoxide disolvate.

In the title compound, C(12)H(12)N(2)O(3)S·2C(2)H(6)OS, the acetic acid and cinnamoyl groups adopt Z and E configurations, respectively, with respect to the thio group about the C-N bonds. The components of the asymmetric unit are connected by N-H⋯O and O-H⋯O hydrogen bonds and in the crystal weak inter-molecular C-H⋯O and C-H⋯S hydrogen bonds further connect the components into chains along the b axis. In the main mol-ecule, an intra-molecular N-H⋯O hydrogen bond is also present.

Related literature

For related structures, see: Hassan et al. (2009 ▶, 2010a ▶,b ▶,c ▶, 2011 ▶); Nasir et al. (2011 ▶). For the synthesis, see: Hassan et al. (2008 ▶). For standard bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C12H12N2O3S·2C2H6OS

M = 420.55

Triclinic,

a = 7.327 (3) Å

b = 12.064 (5) Å

c = 13.691 (6) Å

α = 65.794 (8)°

β = 75.603 (9)°

γ = 85.484 (9)°

V = 1068.6 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.37 mm−1

T = 298 K

0.42 × 0.21 × 0.18 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.859, T max = 0.936

10964 measured reflections

3774 independent reflections

2650 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.085

wR(F 2) = 0.251

S = 1.06

3774 reflections

240 parameters

H-atom parameters constrained

Δρmax = 0.72 e Å−3

Δρmin = −0.25 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 ▶) and SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811036750/lh5324sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811036750/lh5324Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811036750/lh5324Isup3.cml

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

C12H12N2O3S·2C2H6OS	Z = 2
Mr = 420.55	F(000) = 444
Triclinic, P1	Dx = 1.307 Mg m−3
Hall symbol: -P 1	Melting point: 407 K
a = 7.327 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.064 (5) Å	θ = 1.7–25.0°
c = 13.691 (6) Å	µ = 0.37 mm−1
α = 65.794 (8)°	T = 298 K
β = 75.603 (9)°	Block, colourless
γ = 85.484 (9)°	0.42 × 0.21 × 0.18 mm
V = 1068.6 (8) Å3

Bruker SMART APEX CCD diffractometer	3774 independent reflections
Radiation source: fine-focus sealed tube	2650 reflections with I > 2σ(I)
graphite	Rint = 0.046
ω scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.859, Tmax = 0.936	k = −14→14
10964 measured reflections	l = −16→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)] = 0.085	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.251	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.1544P)2 + 0.4047P] where P = (Fo2 + 2Fc2)/3
3774 reflections	(Δ/σ)max < 0.001
240 parameters	Δρmax = 0.72 e Å−3
0 restraints	Δρmin = −0.25 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	0.4518 (2)	0.84669 (10)	0.40846 (9)	0.0689 (5)
S2	0.3003 (3)	1.64039 (11)	0.16460 (11)	0.0800 (6)
S3	0.66629 (18)	0.58770 (10)	0.36710 (9)	0.0580 (4)
O1	0.6554 (5)	1.1084 (3)	0.0515 (2)	0.0642 (10)
O2	0.4605 (6)	1.3125 (3)	0.1829 (3)	0.0754 (11)
O3	0.2971 (6)	1.3022 (3)	0.3467 (3)	0.0697 (11)
H3A	0.3008	1.3765	0.3147	0.105*
O4	0.2660 (7)	1.5335 (3)	0.2747 (3)	0.0836 (13)
O5	0.7343 (5)	0.6780 (3)	0.2502 (2)	0.0626 (9)
N1	0.6120 (5)	0.9232 (3)	0.1959 (3)	0.0457 (9)
H1A	0.6309	0.8470	0.2128	0.055*
N2	0.4931 (5)	1.0710 (3)	0.2566 (3)	0.0495 (9)
H2A	0.5327	1.1210	0.1891	0.059*
C1	0.9539 (8)	0.8304 (6)	−0.1493 (5)	0.0762 (16)
H1	0.9122	0.7733	−0.0774	0.091*
C2	1.0432 (9)	0.7939 (8)	−0.2298 (6)	0.097 (2)
H2	1.0635	0.7115	−0.2118	0.116*
C3	1.1037 (10)	0.8736 (11)	−0.3359 (8)	0.116 (3)
H3	1.1623	0.8466	−0.3903	0.139*
C4	1.0773 (10)	0.9927 (10)	−0.3607 (5)	0.105 (3)
H4	1.1197	1.0486	−0.4331	0.126*
C5	0.9890 (8)	1.0335 (7)	−0.2812 (4)	0.0843 (18)
H5	0.9724	1.1163	−0.2998	0.101*
C6	0.9249 (7)	0.9513 (5)	−0.1739 (4)	0.0648 (13)
C7	0.8281 (7)	0.9974 (5)	−0.0920 (4)	0.0618 (13)
H7A	0.8061	1.0803	−0.1186	0.074*
C8	0.7671 (7)	0.9352 (4)	0.0163 (4)	0.0608 (13)
H8A	0.7811	0.8514	0.0475	0.073*
C9	0.6774 (6)	0.9993 (4)	0.0869 (3)	0.0492 (11)
C10	0.5195 (6)	0.9548 (4)	0.2819 (3)	0.0444 (10)
C11	0.4015 (7)	1.1193 (4)	0.3357 (3)	0.0491 (11)
H11A	0.4714	1.0991	0.3921	0.059*
H11B	0.2754	1.0838	0.3711	0.059*
C12	0.3910 (6)	1.2548 (4)	0.2786 (3)	0.0492 (11)
C13	0.1632 (10)	1.6099 (7)	0.0894 (5)	0.106 (2)
H13A	0.1832	1.5281	0.0948	0.159*
H13B	0.1992	1.6657	0.0134	0.159*
H13C	0.0324	1.6191	0.1188	0.159*
C14	0.5210 (8)	1.6206 (5)	0.0879 (4)	0.0731 (15)
H14A	0.6180	1.6301	0.1201	0.110*
H14B	0.5404	1.6803	0.0134	0.110*
H14C	0.5254	1.5407	0.0884	0.110*
C15	0.8192 (9)	0.6064 (6)	0.4402 (4)	0.0790 (16)
H15A	0.9473	0.6011	0.4033	0.118*
H15B	0.7928	0.5438	0.5136	0.118*
H15C	0.8011	0.6846	0.4436	0.118*
C16	0.7496 (11)	0.4446 (5)	0.3663 (5)	0.093 (2)
H16A	0.6882	0.4229	0.3220	0.139*
H16B	0.7219	0.3834	0.4403	0.139*
H16C	0.8833	0.4507	0.3360	0.139*

	U11	U22	U33	U12	U13	U23
S1	0.1061 (11)	0.0398 (7)	0.0338 (6)	0.0062 (6)	0.0081 (6)	−0.0032 (5)
S2	0.1332 (14)	0.0414 (7)	0.0428 (7)	0.0122 (7)	−0.0026 (7)	−0.0070 (6)
S3	0.0743 (8)	0.0416 (6)	0.0401 (6)	0.0072 (5)	−0.0023 (5)	−0.0063 (5)
O1	0.101 (3)	0.0401 (17)	0.0329 (16)	0.0086 (16)	−0.0024 (16)	−0.0054 (13)
O2	0.125 (3)	0.0399 (17)	0.0402 (19)	0.0064 (18)	0.0049 (19)	−0.0102 (15)
O3	0.115 (3)	0.0444 (18)	0.0399 (17)	0.0144 (19)	−0.0037 (18)	−0.0176 (15)
O4	0.148 (4)	0.0432 (19)	0.0376 (18)	0.017 (2)	0.000 (2)	−0.0100 (15)
O5	0.100 (3)	0.0400 (16)	0.0360 (17)	0.0079 (16)	−0.0103 (16)	−0.0081 (14)
N1	0.069 (2)	0.0281 (16)	0.0323 (17)	0.0028 (15)	−0.0075 (16)	−0.0075 (14)
N2	0.071 (2)	0.0331 (18)	0.0317 (18)	0.0024 (16)	−0.0019 (16)	−0.0070 (14)
C1	0.076 (4)	0.087 (4)	0.063 (3)	0.011 (3)	−0.005 (3)	−0.036 (3)
C2	0.079 (4)	0.133 (6)	0.102 (6)	0.017 (4)	−0.012 (4)	−0.079 (5)
C3	0.078 (5)	0.205 (10)	0.105 (6)	−0.006 (6)	0.001 (4)	−0.114 (7)
C4	0.087 (5)	0.180 (9)	0.043 (3)	−0.043 (5)	0.013 (3)	−0.049 (5)
C5	0.083 (4)	0.105 (5)	0.041 (3)	−0.022 (3)	0.010 (3)	−0.016 (3)
C6	0.061 (3)	0.083 (4)	0.048 (3)	0.002 (3)	−0.005 (2)	−0.028 (3)
C7	0.080 (3)	0.057 (3)	0.040 (2)	0.002 (2)	−0.005 (2)	−0.016 (2)
C8	0.080 (3)	0.044 (3)	0.046 (3)	0.002 (2)	−0.002 (2)	−0.014 (2)
C9	0.066 (3)	0.038 (2)	0.034 (2)	0.0030 (19)	−0.004 (2)	−0.0099 (18)
C10	0.058 (3)	0.036 (2)	0.035 (2)	0.0030 (18)	−0.0094 (19)	−0.0114 (17)
C11	0.065 (3)	0.044 (2)	0.030 (2)	0.004 (2)	−0.0035 (19)	−0.0121 (18)
C12	0.068 (3)	0.044 (2)	0.035 (2)	0.006 (2)	−0.011 (2)	−0.0163 (19)
C13	0.091 (5)	0.121 (6)	0.063 (4)	−0.011 (4)	−0.010 (3)	0.004 (4)
C14	0.095 (4)	0.069 (3)	0.042 (3)	−0.011 (3)	−0.011 (3)	−0.010 (2)
C15	0.097 (4)	0.079 (4)	0.049 (3)	0.020 (3)	−0.015 (3)	−0.019 (3)
C16	0.130 (5)	0.037 (3)	0.076 (4)	0.007 (3)	0.008 (4)	−0.007 (3)

S1—C10	1.664 (4)	C4—C5	1.372 (9)
S2—O4	1.506 (3)	C4—H4	0.9300
S2—C14	1.754 (6)	C5—C6	1.378 (7)
S2—C13	1.757 (7)	C5—H5	0.9300
S3—O5	1.501 (3)	C6—C7	1.457 (7)
S3—C15	1.758 (6)	C7—C8	1.331 (6)
S3—C16	1.789 (6)	C7—H7A	0.9300
O1—C9	1.215 (5)	C8—C9	1.477 (6)
O2—C12	1.199 (5)	C8—H8A	0.9300
O3—C12	1.313 (5)	C11—C12	1.500 (6)
O3—H3A	0.8200	C11—H11A	0.9700
N1—C9	1.375 (5)	C11—H11B	0.9700
N1—C10	1.386 (5)	C13—H13A	0.9600
N1—H1A	0.8600	C13—H13B	0.9600
N2—C10	1.310 (5)	C13—H13C	0.9600
N2—C11	1.434 (5)	C14—H14A	0.9600
N2—H2A	0.8600	C14—H14B	0.9600
C1—C2	1.353 (8)	C14—H14C	0.9600
C1—C6	1.368 (8)	C15—H15A	0.9600
C1—H1	0.9300	C15—H15B	0.9600
C2—C3	1.353 (12)	C15—H15C	0.9600
C2—H2	0.9300	C16—H16A	0.9600
C3—C4	1.344 (13)	C16—H16B	0.9600
C3—H3	0.9300	C16—H16C	0.9600
O4—S2—C14	106.8 (3)	O1—C9—C8	123.3 (4)
O4—S2—C13	105.6 (3)	N1—C9—C8	113.7 (4)
C14—S2—C13	97.0 (3)	N2—C10—N1	116.2 (3)
O5—S3—C15	105.7 (3)	N2—C10—S1	124.2 (3)
O5—S3—C16	104.9 (2)	N1—C10—S1	119.6 (3)
C15—S3—C16	97.7 (3)	N2—C11—C12	109.5 (3)
C12—O3—H3A	109.5	N2—C11—H11A	109.8
C9—N1—C10	127.7 (3)	C12—C11—H11A	109.8
C9—N1—H1A	116.1	N2—C11—H11B	109.8
C10—N1—H1A	116.1	C12—C11—H11B	109.8
C10—N2—C11	123.4 (3)	H11A—C11—H11B	108.2
C10—N2—H2A	118.3	O2—C12—O3	124.4 (4)
C11—N2—H2A	118.3	O2—C12—C11	124.1 (4)
C2—C1—C6	119.9 (6)	O3—C12—C11	111.5 (4)
C2—C1—H1	120.0	S2—C13—H13A	109.5
C6—C1—H1	120.0	S2—C13—H13B	109.5
C1—C2—C3	122.0 (8)	H13A—C13—H13B	109.5
C1—C2—H2	119.0	S2—C13—H13C	109.5
C3—C2—H2	119.0	H13A—C13—H13C	109.5
C4—C3—C2	118.5 (6)	H13B—C13—H13C	109.5
C4—C3—H3	120.8	S2—C14—H14A	109.5
C2—C3—H3	120.8	S2—C14—H14B	109.5
C3—C4—C5	121.3 (7)	H14A—C14—H14B	109.5
C3—C4—H4	119.4	S2—C14—H14C	109.5
C5—C4—H4	119.4	H14A—C14—H14C	109.5
C4—C5—C6	119.7 (7)	H14B—C14—H14C	109.5
C4—C5—H5	120.1	S3—C15—H15A	109.5
C6—C5—H5	120.1	S3—C15—H15B	109.5
C1—C6—C5	118.5 (5)	H15A—C15—H15B	109.5
C1—C6—C7	123.1 (5)	S3—C15—H15C	109.5
C5—C6—C7	118.4 (5)	H15A—C15—H15C	109.5
C8—C7—C6	127.9 (5)	H15B—C15—H15C	109.5
C8—C7—H7A	116.0	S3—C16—H16A	109.5
C6—C7—H7A	116.0	S3—C16—H16B	109.5
C7—C8—C9	119.9 (4)	H16A—C16—H16B	109.5
C7—C8—H8A	120.0	S3—C16—H16C	109.5
C9—C8—H8A	120.0	H16A—C16—H16C	109.5
O1—C9—N1	122.9 (4)	H16B—C16—H16C	109.5
C6—C1—C2—C3	−0.9 (10)	C10—N1—C9—O1	−2.1 (8)
C1—C2—C3—C4	1.5 (12)	C10—N1—C9—C8	−179.0 (4)
C2—C3—C4—C5	−0.8 (12)	C7—C8—C9—O1	−0.2 (8)
C3—C4—C5—C6	−0.3 (11)	C7—C8—C9—N1	176.6 (4)
C2—C1—C6—C5	−0.2 (9)	C11—N2—C10—N1	−179.4 (4)
C2—C1—C6—C7	179.3 (6)	C11—N2—C10—S1	−0.1 (7)
C4—C5—C6—C1	0.8 (9)	C9—N1—C10—N2	−0.9 (7)
C4—C5—C6—C7	−178.7 (6)	C9—N1—C10—S1	179.8 (4)
C1—C6—C7—C8	5.5 (9)	C10—N2—C11—C12	−178.7 (4)
C5—C6—C7—C8	−175.0 (6)	N2—C11—C12—O2	−4.4 (7)
C6—C7—C8—C9	177.8 (5)	N2—C11—C12—O3	175.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O5	0.86	2.02	2.867 (5)	167.
N2—H2A···O1	0.86	1.94	2.625 (4)	136.
O3—H3A···O4	0.82	1.76	2.562 (5)	166.
C14—H14C···O2	0.96	2.54	3.423 (8)	153
C14—H14A···O5i	0.96	2.43	3.319 (7)	154
C15—H15B···O4ii	0.96	2.58	3.468 (7)	153
C16—H16B···S1iii	0.96	2.85	3.702 (7)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O5	0.86	2.02	2.867 (5)	167
N2—H2A⋯O1	0.86	1.94	2.625 (4)	136
O3—H3A⋯O4	0.82	1.76	2.562 (5)	166
C14—H14C⋯O2	0.96	2.54	3.423 (8)	153
C14—H14A⋯O5i	0.96	2.43	3.319 (7)	154
C15—H15B⋯O4ii	0.96	2.58	3.468 (7)	153
C16—H16B⋯S1iii	0.96	2.85	3.702 (7)	148

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