2-Hy­droxy-5-nitro-N-phenyl­benzamide

Raza, A.R.; Nisar, B.; Tahir, M.N.

doi:10.1107/S1600536810024621

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1852

doi:10.1107/S1600536810024621

Open

access

2-Hydroxy-5-nitro-N-phenylbenzamide

Abdul Rauf Raza,^a Bushra Nisar ^a and M. Nawaz Tahir ^b ^*

^aDepartment of Chemistry, University of Sargodha, Sargodha, Pakistan, and ^bDepartment of Physics, University of Sargodha, Sargodha, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 22 June 2010; accepted 23 June 2010; online 26 June 2010)

The molecule of the title compound, C₁₃H₁₀N₂O₄, is almost planar with a dihedral angle between the benzene rings of 1.99 (13)°. The nitro group and its parent benzene ring are oriented at a dihedral angle of 7.6 (3)°. Intramolecular C—H⋯O and N—H⋯O hydrogen bonds form two planar S(6) motifs. Intermolecular O—H⋯O=C hydrogen bonds join molecules into chains extending along the c axis.

Related literature

For similar structures, see: Raza et al. (2009a ,b ). For graph-set notation of hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₃H₁₀N₂O₄
M_r = 258.23
Monoclinic, P c
a = 9.9012 (2) Å
b = 4.7821 (1) Å
c = 12.3369 (4) Å
β = 97.919 (1)°
V = 578.56 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 296 K
0.34 × 0.12 × 0.10 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.979, T_max = 0.988
4381 measured reflections
1042 independent reflections
966 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.071
S = 1.06
1042 reflections
173 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O4ⁱ	0.82	1.79	2.609 (2)	176
N2—H2A⋯O1	0.86	1.95	2.675 (2)	141
C2—H2⋯O4ⁱ	0.93	2.54	3.212 (3)	130
C9—H9⋯O4	0.93	2.26	2.853 (3)	121
C11—H11⋯O2ⁱⁱ	0.93	2.59	3.335 (4)	137
Symmetry codes: (i) $[x, -y+2, z-{\script{1\over 2}}]$ ; (ii) x-1, y-2, z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810024621/gk2288sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810024621/gk2288Isup2.hkl

checkCIF report

Comment top

The title compound (I), (Fig. 1) has been synthesized as a precursor for benzoxazepines.

Previously, we have reported the crystal structures of N-phenyl-2-hydroxy-3-nitrobenzamide (Raza et al., 2009a). The title compound differs from it due to the attachement of nitro group at position-5 instead of position-3. We, also have reported the crystal structure of 2-hydroxy-5-nitrobenzamide (Raza et al., 2009b) which is related to (I).

In (I), the phenyl rings, A (C1–C6) of 2-hydroxy-5-nitrobenzamide and B (C8–C13) attached with 2-hydroxy-5-nitrobenzamide are planar with r. m. s. deviation of 0.0027 Å and 0.0031 Å, respectively. The O-atom of hydroxy group is at a distance of 0.014 (3) Å from the mean square plane of parent ring A. Nitro group C (O2/N1/O3) is of course planar. The dihedral angle between A/B, A/C and B/C is 1.99 (13)°, 7.63 (33)° and 6.20 (34)°, respectively. There exist a weak intramolecular H-bonding of C—H···O type forming an S(5) and a S(6) ring motif (Bernstein et al., 1995), whereas H-bonding of N—H···O type complete an S(6) ring motif. The intermolecular H-bonding of C—H···O and O—H···O types complete R₂¹(6) ring motif (Table 1, Fig. 2). The molecules are essentially stabilized in the form of one dimensional chains extending along the c-axis. However, weak interactions of C—H···O type form 2-dimensional polymeric sheets (Fig. 2).

Related literature top

For similar structures, see: Raza et al. (2009a,b). For graph-set notation of hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

A solution of N-pheny-2-hydroxybenzamide (5.3 g, 0.025 mol) in ethyl acetate (EtOAc) (25 mL) was added dropwise to a nitrating mixture of HNO₃ (2.25 mL, 3.15 g , 0.05 mol) and H₂SO₄ (1.33 mL, 2.45 g, 0.025 mol) with constant stirring while the temperature was kept below 278 K. The reaction mixture was refluxed for 5 h, cooled to room temperature, neutralized with aqueous NaHCO₃ (10%) and extracted with EtOAc (3 × 25 mL). The organic extract was combined, dried over anhydrous Na₂SO₄, filtered and concentrated under reduced pressure to afford reddish brown solid. The column chromatographic purification with 0, 2.5, and 5 % EtOAc in n-hexane (0.5 L each) over a silica gel packed column (25.5 cm) afforded the title compound I in 5th-34th fraction of 50 mL each upon leaving at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. View of the title compound with the atom numbering scheme. The displacement ellipsoids are drawn at the 50% probability level. H-atoms are shown by small circles of arbitrary radii.
	Fig. 2. The partial packing (PLATON; Spek, 2009) which shows that molecules form polymeric chains extending along the c-axis. Hydrogen bonds are shown by dashed lines.

2-Hydroxy-5-nitro-N-phenylbenzamide top

Crystal data top

C₁₃H₁₀N₂O₄	F(000) = 268
M_r = 258.23	D_x = 1.482 Mg m⁻³
Monoclinic, Pc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yc	Cell parameters from 931 reflections
a = 9.9012 (2) Å	θ = 2.8–26.0°
b = 4.7821 (1) Å	µ = 0.11 mm⁻¹
c = 12.3369 (4) Å	T = 296 K
β = 97.919 (1)°	Needle, colorless
V = 578.56 (3) Å³	0.34 × 0.12 × 0.10 mm
Z = 2

Data collection top

Bruker Kappa APEXII CCD diffractometer	1042 independent reflections
Radiation source: fine-focus sealed tube	966 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
Detector resolution: 8.20 pixels mm^-1	θ_max = 25.3°, θ_min = 3.7°
ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −5→5
T_min = 0.979, T_max = 0.988	l = −14→14
4381 measured reflections

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.071	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0447P)² + 0.0284P] where P = (F_o² + 2F_c²)/3
1042 reflections	(Δ/σ)_max < 0.001
173 parameters	Δρ_max = 0.13 e Å⁻³
2 restraints	Δρ_min = −0.13 e Å⁻³

Crystal data top

C₁₃H₁₀N₂O₄	V = 578.56 (3) Å³
M_r = 258.23	Z = 2
Monoclinic, Pc	Mo Kα radiation
a = 9.9012 (2) Å	µ = 0.11 mm⁻¹
b = 4.7821 (1) Å	T = 296 K
c = 12.3369 (4) Å	0.34 × 0.12 × 0.10 mm
β = 97.919 (1)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	1042 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	966 reflections with I > 2σ(I)
T_min = 0.979, T_max = 0.988	R_int = 0.022
4381 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	2 restraints
wR(F²) = 0.071	H-atom parameters constrained
S = 1.06	Δρ_max = 0.13 e Å⁻³
1042 reflections	Δρ_min = −0.13 e Å⁻³
173 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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
O1	0.87642 (17)	0.9971 (4)	−0.04316 (13)	0.0503 (6)
O2	1.3304 (2)	1.6021 (5)	0.27212 (18)	0.0782 (8)
O3	1.2680 (2)	1.2889 (5)	0.38093 (16)	0.0688 (8)
O4	0.88497 (17)	0.7133 (3)	0.27868 (13)	0.0484 (5)
N1	1.25998 (19)	1.4015 (5)	0.29149 (17)	0.0502 (7)
N2	0.78477 (17)	0.6615 (4)	0.10417 (14)	0.0398 (6)
C1	0.9697 (2)	1.0963 (5)	0.03785 (17)	0.0374 (7)
C2	1.0633 (2)	1.2998 (5)	0.01674 (19)	0.0452 (8)
C3	1.1591 (2)	1.4007 (5)	0.09772 (19)	0.0440 (8)
C4	1.1606 (2)	1.2957 (5)	0.20283 (19)	0.0395 (7)
C5	1.0696 (2)	1.0964 (5)	0.22608 (17)	0.0382 (7)
C6	0.9712 (2)	0.9923 (4)	0.14475 (17)	0.0353 (7)
C7	0.8756 (2)	0.7790 (4)	0.18042 (17)	0.0356 (6)
C8	0.6844 (2)	0.4564 (4)	0.11679 (19)	0.0378 (7)
C9	0.6723 (3)	0.3201 (5)	0.2141 (2)	0.0467 (8)
C10	0.5716 (3)	0.1191 (5)	0.2159 (2)	0.0562 (9)
C11	0.4843 (3)	0.0530 (5)	0.1231 (3)	0.0565 (9)
C12	0.4959 (2)	0.1904 (5)	0.0268 (2)	0.0563 (9)
C13	0.5957 (3)	0.3893 (5)	0.0230 (2)	0.0494 (8)
H1	0.88228	1.08314	−0.09982	0.0754*
H2	1.06061	1.36856	−0.05404	0.0542*
H2A	0.78731	0.71755	0.03824	0.0477*
H3	1.22149	1.53593	0.08284	0.0528*
H5	1.07351	1.02973	0.29727	0.0459*
H9	0.73090	0.36301	0.27744	0.0561*
H10	0.56322	0.02735	0.28111	0.0674*
H11	0.41778	−0.08347	0.12537	0.0677*
H12	0.43598	0.14877	−0.03597	0.0675*
H13	0.60379	0.47916	−0.04261	0.0592*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0561 (9)	0.0674 (11)	0.0251 (9)	−0.0152 (8)	−0.0027 (7)	0.0045 (8)
O2	0.0822 (13)	0.0874 (15)	0.0612 (13)	−0.0397 (13)	−0.0041 (10)	−0.0068 (11)
O3	0.0754 (13)	0.0863 (14)	0.0391 (12)	−0.0147 (11)	−0.0117 (9)	0.0010 (10)
O4	0.0645 (10)	0.0525 (9)	0.0267 (9)	−0.0075 (8)	0.0014 (7)	0.0006 (7)
N1	0.0480 (11)	0.0581 (13)	0.0424 (13)	−0.0011 (10)	−0.0009 (9)	−0.0086 (10)
N2	0.0470 (11)	0.0462 (11)	0.0258 (10)	−0.0058 (8)	0.0041 (8)	0.0007 (8)
C1	0.0381 (11)	0.0458 (12)	0.0275 (12)	0.0011 (10)	0.0016 (8)	−0.0024 (9)
C2	0.0503 (14)	0.0554 (14)	0.0301 (13)	−0.0010 (11)	0.0060 (10)	0.0036 (10)
C3	0.0416 (12)	0.0488 (14)	0.0419 (14)	−0.0062 (10)	0.0067 (10)	−0.0030 (11)
C4	0.0372 (11)	0.0447 (12)	0.0356 (13)	0.0026 (10)	0.0014 (9)	−0.0067 (10)
C5	0.0429 (12)	0.0432 (12)	0.0279 (12)	0.0038 (10)	0.0026 (9)	−0.0006 (9)
C6	0.0386 (11)	0.0378 (12)	0.0288 (12)	0.0050 (9)	0.0026 (8)	−0.0015 (8)
C7	0.0427 (11)	0.0380 (11)	0.0258 (11)	0.0029 (10)	0.0032 (8)	−0.0015 (9)
C8	0.0392 (11)	0.0380 (12)	0.0364 (12)	0.0033 (9)	0.0063 (9)	−0.0007 (9)
C9	0.0515 (13)	0.0488 (14)	0.0396 (14)	−0.0017 (11)	0.0056 (10)	0.0038 (11)
C10	0.0593 (15)	0.0536 (15)	0.0581 (18)	−0.0024 (12)	0.0169 (13)	0.0125 (12)
C11	0.0476 (13)	0.0478 (14)	0.075 (2)	−0.0085 (11)	0.0117 (13)	0.0008 (13)
C12	0.0479 (14)	0.0542 (15)	0.0637 (18)	−0.0065 (12)	−0.0030 (12)	−0.0065 (13)
C13	0.0534 (14)	0.0517 (15)	0.0412 (14)	−0.0063 (12)	0.0002 (11)	0.0012 (11)

Geometric parameters (Å, º) top

O1—C1	1.350 (3)	C6—C7	1.498 (3)
O2—N1	1.229 (3)	C8—C13	1.390 (3)
O3—N1	1.221 (3)	C8—C9	1.386 (3)
O4—C7	1.243 (3)	C9—C10	1.387 (4)
O1—H1	0.8200	C10—C11	1.373 (4)
N1—C4	1.457 (3)	C11—C12	1.376 (4)
N2—C8	1.420 (3)	C12—C13	1.377 (3)
N2—C7	1.333 (3)	C2—H2	0.9300
N2—H2A	0.8600	C3—H3	0.9300
C1—C6	1.408 (3)	C5—H5	0.9300
C1—C2	1.393 (3)	C9—H9	0.9300
C2—C3	1.367 (3)	C10—H10	0.9300
C3—C4	1.389 (3)	C11—H11	0.9300
C4—C5	1.369 (3)	C12—H12	0.9300
C5—C6	1.391 (3)	C13—H13	0.9300

O1···N2	2.675 (2)	C8···C11^viii	3.480 (3)
O1···O4ⁱ	2.609 (2)	C8···C6^vii	3.583 (3)
O2···C11ⁱⁱ	3.335 (4)	C8···C1^vii	3.557 (3)
O3···C3ⁱⁱⁱ	3.364 (3)	C9···C7^vii	3.339 (3)
O4···C2^iv	3.212 (3)	C9···O4	2.853 (3)
O4···C9	2.853 (3)	C9···C6^vii	3.556 (3)
O4···O1^iv	2.609 (2)	C10···C7^vii	3.501 (3)
O4···C1^iv	3.319 (3)	C11···C8^vii	3.480 (3)
O1···H2A	1.9500	C11···C3^xi	3.599 (4)
O2···H3	2.4500	C11···O2^xii	3.335 (4)
O2···H12^v	2.7300	C1···H2A	2.5600
O2···H11ⁱⁱ	2.5900	C7···H9	2.8100
O3···H5	2.4000	C7···H1^iv	2.7800
O3···H12^vi	2.7800	H1···H2	2.2400
O3···H2ⁱⁱⁱ	2.8300	H1···O4ⁱ	1.7900
O3···H3ⁱⁱⁱ	2.7300	H1···C7ⁱ	2.7800
O4···H5	2.3900	H1···H5ⁱ	2.4800
O4···H9	2.2600	H2···H1	2.2400
O4···H1^iv	1.7900	H2···O3^x	2.8300
O4···H2^iv	2.5400	H2···O4ⁱ	2.5400
N2···O1	2.675 (2)	H2A···O1	1.9500
N2···C1^vii	3.426 (3)	H2A···C1	2.5600
C1···N2^viii	3.426 (3)	H2A···H13	2.2600
C1···C8^viii	3.557 (3)	H3···O2	2.4500
C1···O4ⁱ	3.319 (3)	H3···O3^x	2.7300
C2···O4ⁱ	3.212 (3)	H5···O3	2.4000
C3···C6^viii	3.478 (3)	H5···O4	2.3900
C3···C11^ix	3.599 (4)	H5···H1^iv	2.4800
C3···O3^x	3.364 (3)	H9···O4	2.2600
C6···C8^viii	3.583 (3)	H9···C7	2.8100
C6···C3^vii	3.478 (3)	H11···O2^xii	2.5900
C6···C9^viii	3.556 (3)	H12···O2^xiii	2.7300
C7···C10^viii	3.501 (3)	H12···O3^xiv	2.7800
C7···C9^viii	3.339 (3)	H13···H2A	2.2600

C1—O1—H1	109.00	N2—C8—C13	116.1 (2)
O2—N1—O3	123.5 (2)	C9—C8—C13	119.5 (2)
O2—N1—C4	117.9 (2)	C8—C9—C10	119.2 (2)
O3—N1—C4	118.6 (2)	C9—C10—C11	121.2 (2)
C7—N2—C8	128.92 (18)	C10—C11—C12	119.5 (2)
C8—N2—H2A	116.00	C11—C12—C13	120.3 (2)
C7—N2—H2A	116.00	C8—C13—C12	120.3 (2)
O1—C1—C2	120.8 (2)	C1—C2—H2	119.00
O1—C1—C6	119.16 (19)	C3—C2—H2	119.00
C2—C1—C6	120.04 (19)	C2—C3—H3	121.00
C1—C2—C3	121.5 (2)	C4—C3—H3	121.00
C2—C3—C4	118.2 (2)	C4—C5—H5	120.00
N1—C4—C3	119.6 (2)	C6—C5—H5	119.00
N1—C4—C5	118.7 (2)	C8—C9—H9	120.00
C3—C4—C5	121.7 (2)	C10—C9—H9	120.00
C4—C5—C6	120.9 (2)	C9—C10—H10	119.00
C5—C6—C7	116.10 (18)	C11—C10—H10	119.00
C1—C6—C7	126.17 (19)	C10—C11—H11	120.00
C1—C6—C5	117.73 (19)	C12—C11—H11	120.00
O4—C7—N2	122.28 (19)	C11—C12—H12	120.00
O4—C7—C6	119.55 (18)	C13—C12—H12	120.00
N2—C7—C6	118.16 (18)	C8—C13—H13	120.00
N2—C8—C9	124.4 (2)	C12—C13—H13	120.00

O3—N1—C4—C3	−173.4 (2)	N1—C4—C5—C6	178.9 (2)
O2—N1—C4—C5	−171.8 (2)	C3—C4—C5—C6	−0.4 (3)
O2—N1—C4—C3	7.4 (3)	C4—C5—C6—C1	0.8 (3)
O3—N1—C4—C5	7.4 (3)	C4—C5—C6—C7	−178.9 (2)
C8—N2—C7—C6	179.93 (17)	C1—C6—C7—N2	4.2 (3)
C7—N2—C8—C9	−6.5 (3)	C5—C6—C7—O4	2.4 (3)
C8—N2—C7—O4	1.4 (3)	C5—C6—C7—N2	−176.16 (19)
C7—N2—C8—C13	174.8 (2)	C1—C6—C7—O4	−177.2 (2)
C6—C1—C2—C3	0.8 (3)	N2—C8—C9—C10	−178.7 (2)
O1—C1—C6—C5	179.3 (2)	C13—C8—C9—C10	0.0 (4)
O1—C1—C2—C3	−179.5 (2)	N2—C8—C13—C12	179.3 (2)
C2—C1—C6—C5	−1.0 (3)	C9—C8—C13—C12	0.5 (4)
C2—C1—C6—C7	178.6 (2)	C8—C9—C10—C11	0.1 (4)
O1—C1—C6—C7	−1.2 (3)	C9—C10—C11—C12	−0.7 (4)
C1—C2—C3—C4	−0.3 (3)	C10—C11—C12—C13	1.1 (4)
C2—C3—C4—C5	0.1 (3)	C11—C12—C13—C8	−1.0 (4)
C2—C3—C4—N1	−179.1 (2)

Symmetry codes: (i) x, −y+2, z−1/2; (ii) x+1, y+2, z; (iii) x, −y+3, z+1/2; (iv) x, −y+2, z+1/2; (v) x+1, −y+2, z+1/2; (vi) x+1, −y+1, z+1/2; (vii) x, y−1, z; (viii) x, y+1, z; (ix) x+1, y+1, z; (x) x, −y+3, z−1/2; (xi) x−1, y−1, z; (xii) x−1, y−2, z; (xiii) x−1, −y+2, z−1/2; (xiv) x−1, −y+1, z−1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4ⁱ	0.82	1.79	2.609 (2)	176
N2—H2A···O1	0.86	1.95	2.675 (2)	141
C2—H2···O4ⁱ	0.93	2.54	3.212 (3)	130
C5—H5···O4	0.93	2.39	2.729 (3)	101
C9—H9···O4	0.93	2.26	2.853 (3)	121
C11—H11···O2^xii	0.93	2.59	3.335 (4)	137

Symmetry codes: (i) x, −y+2, z−1/2; (xii) x−1, y−2, z.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₀N₂O₄
M_r	258.23
Crystal system, space group	Monoclinic, Pc
Temperature (K)	296
a, b, c (Å)	9.9012 (2), 4.7821 (1), 12.3369 (4)
β (°)	97.919 (1)
V (Å³)	578.56 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.34 × 0.12 × 0.10

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.979, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	4381, 1042, 966
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.071, 1.06
No. of reflections	1042
No. of parameters	173
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.13

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4ⁱ	0.82	1.79	2.609 (2)	176
N2—H2A···O1	0.86	1.95	2.675 (2)	141
C2—H2···O4ⁱ	0.93	2.54	3.212 (3)	130
C5—H5···O4	0.93	2.39	2.729 (3)	101
C9—H9···O4	0.93	2.26	2.853 (3)	121
C11—H11···O2ⁱⁱ	0.93	2.59	3.335 (4)	137

Symmetry codes: (i) x, −y+2, z−1/2; (ii) x−1, y−2, z.

Acknowledgements

The authors acknowledge the provision of funds for the purchase of diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan. ARR also acknowledges the Higher Education Commission, Government of Pakistan, for generous support of a research project (20-819).

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573. CrossRef CAS Web of Science Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc. Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Raza, A. R., Danish, M., Tahir, M. N., Nisar, B. & Park, G. (2009a). Acta Cryst. E65, o1042. Web of Science CSD CrossRef IUCr Journals Google Scholar
Raza, A. R., Tahir, M. N., Nisar, B., Danish, M. & Iqbal, M. S. (2009b). Acta Cryst. E65, o3260. Web of Science CSD CrossRef IUCr Journals 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