(E)-2-(3-Cinnamoyl­thio­ureido)acetic acid dimethyl sulfoxide disolvate

Hassan, I.N.; Wan Daud, W.R.; Yamin, B.M.; Kassim, M.B.

doi:10.1107/S1600536811036750

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 10| October 2011| Page o2686

https://doi.org/10.1107/S1600536811036750

Open

access

(E)-2-(3-Cinnamoylthioureido)acetic acid dimethyl sulfoxide disolvate

Ibrahim N. Hassan,^a ^* Wan Ramli Wan Daud,^b,^a Bohari M. Yamin ^c and Mohammad B. Kassim ^c,^a

^aFuel Cell Institute, Universiti Kebangsaan Malaysia, UKM 43600 Bangi Selangor, Malaysia, ^bDepartment of Chemical and Process Engineering, Faculty of Engineering, Universiti Kebangsaan Malaysia, UKM 43600 Bangi Selangor, Malaysia, and ^cSchool of Chemical Sciences and Food Technology, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, UKM 43600 Bangi Selangor, Malaysia
^*Correspondence e-mail: ibnhum@gmail.com

(Received 22 August 2011; accepted 10 September 2011; online 17 September 2011)

In the title compound, C₁₂H₁₂N₂O₃S·2C₂H₆OS, 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 intermolecular C—H⋯O and C—H⋯S hydrogen bonds further connect the components into chains along the b axis. In the main molecule, an intramolecular 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_r = 420.55
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.085
wR(F²) = 0.251
S = 1.06
3774 reflections
240 parameters
H-atom parameters constrained
Δρ_max = 0.72 e Å⁻³
Δρ_min = −0.25 e Å⁻³

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) x, y+1, z; (ii) -x+1, -y+2, -z+1; (iii) -x+1, -y+1, -z+1.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811036750/lh5324sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811036750/lh5324Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811036750/lh5324Isup3.cml

checkCIF report

Comment top

The title compound (I) is the thiourea carboxylic acid version of our previously reported ester molecules (E)-methyl-2-(3-cinnamoylthioureido)acetate (II) (Hassan et al., 2010a)and (E)-ethyl-2-(3- cinnmoylthioureido)acetate (III) (Hassan et al., 2010b) and analogous to methyl-2-(3-benzoylthioureido)acetate (IV) (Hassan et al., 2009). The molecule maintains the same E-Z configuration with respect to the positions of the acetic acid and cinnamoyl groups, relative to the S atom across the C—N bonds, respectively (Fig. 1). In general, the bond lengths (Allen et al., 1987) and angles in (I) are in normal ranges and comparable to those in (II), (III) and (IV). The the C═S bond length [1.665 (4) Å] is the same within experimental error to that in (II) [1.666 (3) Å] and that of (III) [1.656 (5) Å]. The C7═C8 bond length [1.331 (6) Å] is slightly longer than that reported by Hassan et al. (2010c) [1.320 (3) Å]. The carbonyl C═O bond length [1.215 (5) Å] is the same within experimental error to that reported by Nasir et al. (2011) [1.213 (3) Å]. The S1/O1/O2/N1/N2/C1—C12 fragment is essentially planar with a maximum deviation of 0.043 (5) Å, for atom C7. In the crystal, the components of the asymmtric unit are connected by N—H···O and O—H···O hydrogen bonds and weak intermolecular C—H···O and C—H···S hydrogen bonds connect the components into one-dimensional chains along the b axis (Fig. 2). In the main molecule an intramolecular N—H···O hydrogen bond is also present.

Related literature top

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 top

The title compound was synthesized according to a previously reported method (Hassan et al., 2008). A yellowish crystal, suitable for X-ray crystallography, was obtained by a slow evaporation from CH₂Cl₂ solution at room temperature (yield 79%).

Structure description top

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).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of (I), with displacement ellipsoids are drawn at the 50% probability level. Hydrogen bonds are shown as dashed lines.
	Fig. 2. A packing diagram of (I) viewed along the c axis. Hydrogen bonds are shown by dashed lines.

(E)-2-(3-Cinnamoylthioureido)acetic acid dimethyl sulfoxide disolvate top

Crystal data top

C₁₂H₁₂N₂O₃S·2C₂H₆OS	Z = 2
M_r = 420.55	F(000) = 444
Triclinic, P1	D_x = 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

Data collection top

Bruker SMART APEX CCD diffractometer	3774 independent reflections
Radiation source: fine-focus sealed tube	2650 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.046
ω scans	θ_max = 25.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
T_min = 0.859, T_max = 0.936	k = −14→14
10964 measured reflections	l = −16→16

Refinement top

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(F_o²) + (0.1544P)² + 0.4047P] where P = (F_o² + 2F_c²)/3
3774 reflections	(Δ/σ)_max < 0.001
240 parameters	Δρ_max = 0.72 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₂H₁₂N₂O₃S·2C₂H₆OS	γ = 85.484 (9)°
M_r = 420.55	V = 1068.6 (8) Å³
Triclinic, P1	Z = 2
a = 7.327 (3) Å	Mo Kα radiation
b = 12.064 (5) Å	µ = 0.37 mm⁻¹
c = 13.691 (6) Å	T = 298 K
α = 65.794 (8)°	0.42 × 0.21 × 0.18 mm
β = 75.603 (9)°

Data collection top

Bruker SMART APEX CCD diffractometer	3774 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2650 reflections with I > 2σ(I)
T_min = 0.859, T_max = 0.936	R_int = 0.046
10964 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.085	0 restraints
wR(F²) = 0.251	H-atom parameters constrained
S = 1.06	Δρ_max = 0.72 e Å⁻³
3774 reflections	Δρ_min = −0.25 e Å⁻³
240 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x, y+1, z; (ii) −x+1, −y+2, −z+1; (iii) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₂N₂O₃S·2C₂H₆OS
M_r	420.55
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	7.327 (3), 12.064 (5), 13.691 (6)
α, β, γ (°)	65.794 (8), 75.603 (9), 85.484 (9)
V (Å³)	1068.6 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.37
Crystal size (mm)	0.42 × 0.21 × 0.18

Data collection
Diffractometer	Bruker SMART APEX CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.859, 0.936
No. of measured, independent and observed [I > 2σ(I)] reflections	10964, 3774, 2650
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.085, 0.251, 1.06
No. of reflections	3774
No. of parameters	240
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.72, −0.25

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996) and SHELXTL (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O5	0.86	2.02	2.867 (5)	167.2
N2—H2A···O1	0.86	1.94	2.625 (4)	136.1
O3—H3A···O4	0.82	1.76	2.562 (5)	166.0
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) x, y+1, z; (ii) −x+1, −y+2, −z+1; (iii) −x+1, −y+1, −z+1.

Acknowledgements

The authors thank Universiti Kebangsaan Malaysia for providing facilities and grants (postdoctoral for INH, UKM-GUP-BTT-07–30-190 and UKM-OUP-TK-16–73/2010&2011) and the Kementerian Pengajian Tinggi, Malaysia, for the research fund No. UKM-ST-06-FRGS0111–2009.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CSD CrossRef Web of Science Google Scholar
Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Hassan, I. N., Yamin, B. M. & Kassim, M. B. (2008). Acta Cryst. E64, o1727. Web of Science CSD CrossRef IUCr Journals Google Scholar
Hassan, I. N., Yamin, B. M. & Kassim, M. B. (2009). Acta Cryst. E65, o3078. Web of Science CSD CrossRef IUCr Journals Google Scholar
Hassan, I. N., Yamin, B. M. & Kassim, M. B. (2010a). Acta Cryst. E66, o2242. Web of Science CSD CrossRef IUCr Journals Google Scholar
Hassan, I. N., Yamin, B. M. & Kassim, M. B. (2010b). Acta Cryst. E66, o2784. Web of Science CSD CrossRef IUCr Journals Google Scholar
Hassan, I. N., Yamin, B. M. & Kassim, M. B. (2010c). Acta Cryst. E66, o2796. Web of Science CSD CrossRef IUCr Journals Google Scholar
Hassan, I. N., Yi, C. Y. & Kassim, M. B. (2011). Acta Cryst. E67, o780. Web of Science CSD CrossRef IUCr Journals Google Scholar
Nasir, M. F. M., Hassan, I. N., Wan Daud, W. R., Yamin, B. M. & Kassim, M. B. (2011). Acta Cryst. E67, o1987. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar