Ethyl 2-[3-(3,5-Dinitrobenzo­yl)thio­ureido]benzoate

Saeed, S.; Rashid, N.; Bhatti, M.H.; Wong, W.-T.

doi:10.1107/S1600536811012918

organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page o1114

doi:10.1107/S1600536811012918

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Ethyl 2-[3-(3,5-Dinitrobenzoyl)thioureido]benzoate

Sohail Saeed,^a ^* Naghmana Rashid,^a Moazzam H. Bhatti ^a and Wing-Tak Wong ^b

^aDepartment of Chemistry, Research Complex, Allama Iqbal Open University, Islamabad 44000, Pakistan, and ^bDepartment of Chemistry, The University of Hong Kong, Pokfulam Road, Pokfulam, Hong Kong SAR, People's Republic of China
^*Correspondence e-mail: Sohail262001@yahoo.com

(Received 14 March 2011; accepted 6 April 2011; online 13 April 2011)

In the title compound, C₁₇H₁₄N₄O₇S, the dihedral angle between the two benzene rings is 9.04 (15)°. The centroid–centroid distance of 3.9825 (19) Å between nearly parallel benzene rings of adjacent molecules suggests the existence of π-π stacking. Intermolecular and intra-molecular N—H⋯O hydrogen bonding is present in the structure. The ethoxy group is disordered over two sets of sites with an occupancy ratio of 0.580 (15):0.420 (15). The crystal studied was an inversion twin.

Related literature

For background to the chemistry of thiourea derivatives and their bioloical activity, and a related structure, see: Saeed et al. (2010 ).

Experimental

Crystal data

C₁₇H₁₄N₄O₇S
M_r = 418.38
Monoclinic, C c
a = 11.7264 (19) Å
b = 16.617 (3) Å
c = 9.9630 (16) Å
β = 101.522 (2)°
V = 1902.3 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 299 K
0.27 × 0.16 × 0.08 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.943, T_max = 0.983
4944 measured reflections
3011 independent reflections
2727 reflections with I > 2σ(I)
R_int = 0.014

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.095
S = 1.10
3011 reflections
301 parameters
42 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.24 e Å⁻³
Absolute structure: Flack (1983 ), 1340 Friedel pairs
Flack parameter: 0.39 (8)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2	0.91 (3)	1.95 (3)	2.672 (3)	134 (2)
N1—H1⋯O3	0.91 (3)	2.01 (3)	2.700 (3)	131 (2)
N2—H2⋯O3ⁱ	0.77 (3)	2.32 (3)	3.086 (3)	172 (2)
Symmetry code: (i) $[x, -y, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 2006 ); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811012918/xu5177sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811012918/xu5177Isup2.hkl

checkCIF report

Comment top

The background to this study has been set in our previous work on the structural chemistry of N,N'-disubstituted thiourea (Saeed et al., 2010). Herein, as a continuation of these studies, the structure of the title compound, (I), C₁₇H₁₄N₄O₇S, is described.

The compound is slightly twisted. The nitro groups are 3.9 (5)° and 17 (1)° from the phenyl ring plane of C10—C15. The thiourea plane is making a dihedral angle of 5.3 (2)° with the amido group and makes a dihedral angle of 31.35 (17)° with the phenyl ring plane of C2—C7.

There are inter-molecular N—H···O H-bond interactions which link the molecules to form 1-D chain in the crystal lattice. There are also weak π···π between neighbouring rings in the crystal lattice.

Related literature top

For background to this study and a related structure, see: Saeed et al. (2010).

Experimental top

A solution of 3,5-dinitrobenzoyl chloride (0.01 mol) in anhydrous acetone (75 ml) and 3% tetrabutylammonium bromide (TBAB) as a phase-transfer catalyst (PTC) in anhydrous acetone was added dropwise to a suspension of dry potassium thiocyanate (0.01 mol) in acetone (50 ml) and the reaction mixture was refluxed for 50 min. After cooling to room temperature, a solution of ethyl-orthoamino benzoate (0.01 mol) in anhydrous acetone (25 ml) was added dropwise and the resulting mixture refluxed for 3 h. Hydrochloric acid (0.1 N, 300 ml) was added, and the solution was filtered. The solid product was washed with water and purified by re-crystallization from ethyl acetate.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The ORTEP plot of the compound was shown at 50% probability thermal ellipsoids with the atom numbering scheme (only the major component was shown).
	Fig. 2. Packing diagram of the title compound viewed down the a axis.

Ethyl 2-[3-(3,5-Dinitrobenzoyl)thioureido]benzoate top

Crystal data top

C₁₇H₁₄N₄O₇S	F(000) = 864
M_r = 418.38	D_x = 1.461 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 6458 reflections
a = 11.7264 (19) Å	θ = 2.1–25.0°
b = 16.617 (3) Å	µ = 0.22 mm⁻¹
c = 9.9630 (16) Å	T = 299 K
β = 101.522 (2)°	Block, yellow
V = 1902.3 (5) Å³	0.27 × 0.16 × 0.08 mm
Z = 4

Data collection top

Bruker SMART 1000 CCD diffractometer	3011 independent reflections
Radiation source: fine-focus sealed tube	2727 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.014
ω and ϕ scans	θ_max = 25.0°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −13→13
T_min = 0.943, T_max = 0.983	k = −19→15
4944 measured reflections	l = −11→11

Refinement top

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)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.095	w = 1/[σ²(F_o²) + (0.0536P)² + 0.3273P] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max < 0.001
3011 reflections	Δρ_max = 0.22 e Å⁻³
301 parameters	Δρ_min = −0.24 e Å⁻³
42 restraints	Absolute structure: Flack (1983), 1340 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.39 (8)

Crystal data top

C₁₇H₁₄N₄O₇S	V = 1902.3 (5) Å³
M_r = 418.38	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 11.7264 (19) Å	µ = 0.22 mm⁻¹
b = 16.617 (3) Å	T = 299 K
c = 9.9630 (16) Å	0.27 × 0.16 × 0.08 mm
β = 101.522 (2)°

Data collection top

Bruker SMART 1000 CCD diffractometer	3011 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	2727 reflections with I > 2σ(I)
T_min = 0.943, T_max = 0.983	R_int = 0.014
4944 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.095	Δρ_max = 0.22 e Å⁻³
S = 1.10	Δρ_min = −0.24 e Å⁻³
3011 reflections	Absolute structure: Flack (1983), 1340 Friedel pairs
301 parameters	Absolute structure parameter: 0.39 (8)
42 restraints

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	Occ. (<1)
S1	0.94150 (8)	0.19793 (4)	0.68183 (8)	0.0759 (3)
O2	0.8103 (2)	0.05570 (13)	1.0967 (3)	0.0866 (7)
O3	0.99391 (19)	−0.01499 (10)	0.97679 (18)	0.0663 (5)
O4	1.0187 (3)	−0.31100 (14)	0.9255 (4)	0.1022 (8)
O5	1.1263 (3)	−0.35915 (14)	0.7937 (3)	0.1095 (10)
O6	1.2496 (4)	−0.1832 (2)	0.4646 (3)	0.1355 (14)
O7	1.2710 (4)	−0.0571 (3)	0.5114 (4)	0.1459 (15)
N1	0.9176 (2)	0.13747 (12)	0.9269 (2)	0.0543 (5)
H1	0.911 (2)	0.0912 (17)	0.974 (3)	0.064 (8)*
H2	0.997 (2)	0.0472 (15)	0.704 (3)	0.045 (7)*
N2	0.9902 (2)	0.05353 (12)	0.7789 (2)	0.0555 (5)
N3	1.0798 (3)	−0.30348 (14)	0.8423 (3)	0.0773 (8)
N4	1.2402 (3)	−0.1244 (3)	0.5338 (3)	0.0976 (10)
C1	0.7736 (3)	0.11786 (17)	1.1281 (3)	0.0647 (7)
C2	0.8103 (2)	0.19844 (15)	1.0865 (3)	0.0563 (6)
C3	0.7770 (3)	0.26756 (18)	1.1485 (3)	0.0713 (8)
H3	0.7296	0.2626	1.2125	0.086*
C4	0.8124 (4)	0.3418 (2)	1.1176 (4)	0.0842 (10)
H4	0.7885	0.3870	1.1596	0.101*
C5	0.8830 (3)	0.35007 (17)	1.0248 (3)	0.0782 (9)
H5	0.9080	0.4010	1.0051	0.094*
C6	0.9179 (3)	0.28322 (16)	0.9596 (3)	0.0657 (7)
H6	0.9662	0.2896	0.8968	0.079*
C7	0.8809 (2)	0.20717 (14)	0.9882 (2)	0.0531 (6)
C8	0.9476 (2)	0.13033 (14)	0.8043 (3)	0.0525 (6)
C9	1.0156 (2)	−0.01157 (13)	0.8622 (2)	0.0518 (6)
C10	1.0713 (2)	−0.08065 (14)	0.8043 (3)	0.0539 (6)
C11	1.0528 (2)	−0.15737 (14)	0.8509 (3)	0.0555 (6)
H11	1.0103	−0.1650	0.9193	0.067*
C12	1.0991 (2)	−0.22190 (15)	0.7933 (3)	0.0595 (7)
C13	1.1609 (3)	−0.21360 (18)	0.6905 (3)	0.0695 (8)
H13	1.1890	−0.2582	0.6508	0.083*
C14	1.1797 (3)	−0.1366 (2)	0.6489 (3)	0.0677 (8)
C15	1.1379 (3)	−0.07002 (16)	0.7053 (3)	0.0618 (7)
H15	1.1542	−0.0186	0.6775	0.074*
O1	0.7136 (10)	0.1247 (5)	1.2262 (9)	0.083 (2)	0.580 (15)
C16	0.6730 (10)	0.0532 (7)	1.2838 (13)	0.113 (4)	0.580 (15)
H16A	0.6931	0.0548	1.3830	0.135*	0.580 (15)
H16B	0.7077	0.0056	1.2523	0.135*	0.580 (15)
C17	0.5404 (10)	0.0522 (6)	1.2345 (19)	0.161 (6)	0.580 (15)
H17A	0.5070	0.0125	1.2851	0.193*	0.580 (15)
H17B	0.5219	0.0392	1.1387	0.193*	0.580 (15)
H17C	0.5093	0.1042	1.2489	0.193*	0.580 (15)
O1'	0.6758 (12)	0.1178 (7)	1.1805 (14)	0.085 (3)	0.420 (15)
C16'	0.6436 (15)	0.0411 (7)	1.2287 (14)	0.084 (4)	0.420 (15)
H16C	0.7119	0.0073	1.2549	0.101*	0.420 (15)
H16D	0.5889	0.0139	1.1571	0.101*	0.420 (15)
C17'	0.5883 (19)	0.0568 (8)	1.3511 (18)	0.134 (6)	0.420 (15)
H17D	0.5738	0.0065	1.3920	0.161*	0.420 (15)
H17E	0.5162	0.0850	1.3219	0.161*	0.420 (15)
H17F	0.6399	0.0888	1.4169	0.161*	0.420 (15)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.1117 (6)	0.0590 (4)	0.0655 (4)	0.0263 (4)	0.0381 (4)	0.0158 (3)
O2	0.1105 (17)	0.0589 (12)	0.1056 (17)	0.0112 (11)	0.0580 (14)	0.0120 (11)
O3	0.1054 (16)	0.0478 (10)	0.0498 (10)	0.0112 (9)	0.0252 (10)	−0.0004 (7)
O4	0.131 (2)	0.0570 (13)	0.122 (2)	−0.0046 (13)	0.031 (2)	0.0083 (13)
O5	0.118 (2)	0.0524 (12)	0.153 (3)	0.0257 (13)	0.0147 (19)	−0.0192 (14)
O6	0.172 (3)	0.163 (3)	0.0823 (18)	0.073 (3)	0.052 (2)	−0.0065 (18)
O7	0.179 (4)	0.131 (3)	0.163 (3)	0.028 (3)	0.119 (3)	0.026 (2)
N1	0.0734 (15)	0.0413 (10)	0.0509 (12)	0.0056 (9)	0.0185 (10)	−0.0003 (8)
N2	0.0776 (15)	0.0480 (11)	0.0434 (12)	0.0094 (10)	0.0178 (11)	−0.0029 (9)
N3	0.0820 (18)	0.0479 (13)	0.092 (2)	0.0105 (12)	−0.0056 (16)	−0.0079 (13)
N4	0.099 (2)	0.123 (3)	0.0795 (19)	0.049 (2)	0.0396 (17)	0.0068 (19)
C1	0.076 (2)	0.0658 (17)	0.0559 (15)	0.0108 (14)	0.0209 (14)	0.0059 (12)
C2	0.0635 (17)	0.0569 (14)	0.0459 (13)	0.0114 (11)	0.0046 (12)	−0.0053 (10)
C3	0.081 (2)	0.0679 (18)	0.0663 (18)	0.0144 (14)	0.0178 (16)	−0.0096 (14)
C4	0.103 (3)	0.0639 (19)	0.086 (2)	0.0187 (17)	0.0186 (19)	−0.0250 (16)
C5	0.103 (2)	0.0453 (14)	0.084 (2)	0.0031 (14)	0.0121 (18)	−0.0134 (13)
C6	0.080 (2)	0.0526 (14)	0.0644 (17)	−0.0012 (12)	0.0144 (15)	−0.0065 (12)
C7	0.0631 (16)	0.0459 (12)	0.0478 (13)	0.0070 (10)	0.0049 (12)	−0.0029 (10)
C8	0.0577 (15)	0.0476 (13)	0.0520 (13)	0.0034 (10)	0.0100 (11)	−0.0010 (10)
C9	0.0643 (17)	0.0453 (13)	0.0462 (14)	0.0029 (10)	0.0119 (12)	−0.0023 (10)
C10	0.0649 (17)	0.0507 (13)	0.0445 (12)	0.0062 (11)	0.0069 (12)	−0.0030 (10)
C11	0.0637 (17)	0.0486 (13)	0.0516 (13)	0.0047 (11)	0.0056 (12)	−0.0062 (10)
C12	0.0622 (17)	0.0462 (13)	0.0641 (17)	0.0098 (11)	−0.0015 (14)	−0.0033 (11)
C13	0.0718 (19)	0.0740 (18)	0.0574 (16)	0.0290 (14)	0.0001 (14)	−0.0162 (14)
C14	0.0655 (18)	0.082 (2)	0.0568 (16)	0.0240 (14)	0.0151 (14)	0.0023 (14)
C15	0.0686 (18)	0.0592 (14)	0.0581 (15)	0.0113 (13)	0.0138 (13)	0.0029 (12)
O1	0.103 (6)	0.083 (3)	0.075 (4)	0.006 (3)	0.043 (4)	0.008 (3)
C16	0.130 (8)	0.116 (7)	0.104 (7)	−0.012 (5)	0.053 (6)	0.018 (5)
C17	0.191 (12)	0.086 (5)	0.212 (14)	−0.002 (6)	0.056 (10)	0.002 (7)
O1'	0.087 (6)	0.081 (4)	0.093 (7)	0.005 (4)	0.035 (5)	−0.008 (4)
C16'	0.090 (7)	0.070 (5)	0.108 (8)	−0.013 (4)	0.055 (6)	0.007 (5)
C17'	0.209 (14)	0.092 (7)	0.135 (10)	0.039 (8)	0.116 (10)	0.024 (7)

Geometric parameters (Å, º) top

S1—C8	1.649 (2)	C6—C7	1.385 (4)
O2—C1	1.185 (3)	C6—H6	0.9300
O3—C9	1.219 (3)	C9—C10	1.493 (3)
O4—N3	1.205 (4)	C10—C15	1.386 (4)
O5—N3	1.222 (4)	C10—C11	1.388 (3)
O6—N4	1.213 (4)	C11—C12	1.377 (4)
O7—N4	1.210 (5)	C11—H11	0.9300
N1—C8	1.342 (3)	C12—C13	1.375 (4)
N1—C7	1.416 (3)	C13—C14	1.376 (5)
N1—H1	0.91 (3)	C13—H13	0.9300
N2—C9	1.360 (3)	C14—C15	1.375 (4)
N2—C8	1.412 (3)	C15—H15	0.9300
N2—H2	0.77 (3)	O1—C16	1.442 (8)
N3—C12	1.474 (4)	C16—C17	1.535 (9)
N4—C14	1.478 (4)	C16—H16A	0.9700
C1—O1	1.318 (10)	C16—H16B	0.9700
C1—O1'	1.351 (14)	C17—H17A	0.9600
C1—C2	1.490 (4)	C17—H17B	0.9600
C2—C3	1.396 (4)	C17—H17C	0.9600
C2—C7	1.410 (4)	O1'—C16'	1.440 (9)
C3—C4	1.356 (5)	C16'—C17'	1.514 (9)
C3—H3	0.9300	C16'—H16C	0.9700
C4—C5	1.365 (5)	C16'—H16D	0.9700
C4—H4	0.9300	C17'—H17D	0.9600
C5—C6	1.389 (4)	C17'—H17E	0.9600
C5—H5	0.9300	C17'—H17F	0.9600

C8—N1—C7	128.5 (2)	N2—C9—C10	115.8 (2)
C8—N1—H1	117.1 (18)	C15—C10—C11	120.2 (2)
C7—N1—H1	114.0 (18)	C15—C10—C9	122.0 (2)
C9—N2—C8	130.7 (2)	C11—C10—C9	117.9 (2)
C9—N2—H2	115.4 (18)	C12—C11—C10	118.4 (3)
C8—N2—H2	113.8 (19)	C12—C11—H11	120.8
O4—N3—O5	124.6 (3)	C10—C11—H11	120.8
O4—N3—C12	118.4 (2)	C13—C12—C11	122.8 (3)
O5—N3—C12	117.1 (3)	C13—C12—N3	118.5 (2)
O7—N4—O6	125.1 (4)	C11—C12—N3	118.6 (3)
O7—N4—C14	118.6 (3)	C12—C13—C14	117.2 (2)
O6—N4—C14	116.2 (4)	C12—C13—H13	121.4
O2—C1—O1	123.2 (5)	C14—C13—H13	121.4
O2—C1—O1'	118.9 (6)	C15—C14—C13	122.3 (3)
O2—C1—C2	124.7 (3)	C15—C14—N4	118.1 (3)
O1—C1—C2	110.8 (4)	C13—C14—N4	119.5 (3)
O1'—C1—C2	115.0 (5)	C14—C15—C10	119.0 (3)
C3—C2—C7	118.5 (2)	C14—C15—H15	120.5
C3—C2—C1	119.6 (3)	C10—C15—H15	120.5
C7—C2—C1	121.9 (2)	C1—O1—C16	119.4 (9)
C4—C3—C2	121.5 (3)	O1—C16—C17	106.0 (9)
C4—C3—H3	119.2	O1—C16—H16A	110.5
C2—C3—H3	119.2	C17—C16—H16A	110.5
C3—C4—C5	120.0 (3)	O1—C16—H16B	110.5
C3—C4—H4	120.0	C17—C16—H16B	110.5
C5—C4—H4	120.0	H16A—C16—H16B	108.7
C4—C5—C6	120.7 (3)	C1—O1'—C16'	115.3 (10)
C4—C5—H5	119.6	O1'—C16'—C17'	107.4 (10)
C6—C5—H5	119.6	O1'—C16'—H16C	110.2
C7—C6—C5	120.0 (3)	C17'—C16'—H16C	110.2
C7—C6—H6	120.0	O1'—C16'—H16D	110.2
C5—C6—H6	120.0	C17'—C16'—H16D	110.2
C6—C7—C2	119.3 (2)	H16C—C16'—H16D	108.5
C6—C7—N1	121.5 (2)	C16'—C17'—H17D	109.5
C2—C7—N1	119.1 (2)	C16'—C17'—H17E	109.5
N1—C8—N2	114.2 (2)	H17D—C17'—H17E	109.5
N1—C8—S1	129.22 (19)	C16'—C17'—H17F	109.5
N2—C8—S1	116.62 (19)	H17D—C17'—H17F	109.5
O3—C9—N2	123.2 (2)	H17E—C17'—H17F	109.5
O3—C9—C10	121.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.91 (3)	1.95 (3)	2.672 (3)	134 (2)
N1—H1···O3	0.91 (3)	2.01 (3)	2.700 (3)	131 (2)
N2—H2···O3ⁱ	0.77 (3)	2.32 (3)	3.086 (3)	172 (2)

Symmetry code: (i) x, −y, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₄N₄O₇S
M_r	418.38
Crystal system, space group	Monoclinic, Cc
Temperature (K)	299
a, b, c (Å)	11.7264 (19), 16.617 (3), 9.9630 (16)
β (°)	101.522 (2)
V (Å³)	1902.3 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.27 × 0.16 × 0.08

Data collection
Diffractometer	Bruker SMART 1000 CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.943, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	4944, 3011, 2727
R_int	0.014
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.095, 1.10
No. of reflections	3011
No. of parameters	301
No. of restraints	42
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.24
Absolute structure	Flack (1983), 1340 Friedel pairs
Absolute structure parameter	0.39 (8)

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPII (Johnson, 1976) and Mercury (Macrae et al., 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.91 (3)	1.95 (3)	2.672 (3)	134 (2)
N1—H1···O3	0.91 (3)	2.01 (3)	2.700 (3)	131 (2)
N2—H2···O3ⁱ	0.77 (3)	2.32 (3)	3.086 (3)	172 (2)

Symmetry code: (i) x, −y, z−1/2.

Acknowledgements

The authors are grateful to Allama Iqbal Open University, Islamabad, Pakistan, for the allocation of research and analytical laboratory facilities.

References

Bruker. (1998). SMART, Madison, Wisconsin, USA. Google Scholar
Bruker. (2006). SAINT, Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CrossRef CAS IUCr Journals Google Scholar
Saeed, S., Rashid, N. & Wong, W.-T. (2010). Acta Cryst. E66, o980. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2004). 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