N-Benzyl-N-cyclo­hexyl­benzene­sulfonamide

Haider, Z.; Khan, I.U.; Zia-ur-Rehman, M.; Arshad, M.N.

doi:10.1107/S1600536809046960

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3053

doi:10.1107/S1600536809046960

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N-Benzyl-N-cyclohexylbenzenesulfonamide

Zeeshan Haider,^a Islam Ullah Khan,^a ^* Muhammad Zia-ur-Rehman ^b and Muhammad Nadeem Arshad ^a

^aDepartment of Chemistry, Government College University, Lahore 54000, Pakistan, and ^bApplied Chemistry Research Centre, PCSIR Laboratories Complex, Ferozpure Road, Lahore 54600, Pakistan
^*Correspondence e-mail: iukhan.gcu@gmail.com

(Received 4 November 2009; accepted 6 November 2009; online 11 November 2009)

In the title compound, C₁₉H₂₃NO₂S, the cyclohexyl ring exists in a chair form. The dihedral angle between the two terminal phenyl rings is 86.70 (6)°. No significant interactions are observed except for a weak intramolecular C—H⋯O hydrogen bond.

Related literature

For the biological activity of sulfonamides, see: Innocenti et al. (2004 ); Ozbek et al. (2007 ); Parari et al. (2008 ); Ratish et al. (2009 ); Selnam et al. (2001 ); For related structures, see: Khan et al. (2009 ); Zia-ur-Rehman et al. (2009 ) Gowda et al. (2007a ,b ,c ). For bond length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₉H₂₃NO₂S
M_r = 329.44
Orthorhombic, P 2₁ 2₁ 2₁
a = 9.1996 (5) Å
b = 11.0406 (5) Å
c = 17.1897 (9) Å
V = 1745.94 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 296 K
0.39 × 0.34 × 0.28 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.928, T_max = 0.948
10897 measured reflections
4306 independent reflections
3507 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.094
S = 1.03
4306 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.24 e Å⁻³
Absolute structure: Flack (1983 ), 1853 Friedel pairs
Flack parameter: 0.03 (7)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O2	0.98	2.34	2.874 (2)	113

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and local programs.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809046960/is2484sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809046960/is2484Isup2.hkl

checkCIF report

Comment top

Sulfonamides are familiar as biologically active compounds and possess anti-microbial (Ozbek et al., 2007; Parari et al., 2008), anti-inflamatory (Ratish et al., 2009), anti HIV (Selnam et al., 2001) and carbonic anhydrase inhibiton activity (Innocenti et al., 2004). In the present paper, the structure of N-cyclohexyl-N-propyl benzene sulfonamide has been determined as part of a research program involving the synthesis of various sulfur containing heterocycles (Zia-ur-Rehman et al., 2009; Khan et al., 2009).

In the molecule of (I) (Fig. 1), bond lengths and bond angles are almost similar to those in the related molecules (Gowda et al., 2007a,b,c) and are within normal ranges (Allen et al., 1987). The benzene rings are essentially planar while cyclohexane ring is in the chair form. The dihedral angles between the phenyl (C1–C6) & benzyl ring (C14–C19), the phenyl (C1–C6) ring & the mean plane of cyclohexyl ring (C7–C12), and the benzyl (C14–C19) ring & the mean plane cyclohexyl ring (C7–C12) are 86.70 (6), 42.43 (8) and 55.47 (8)°, respectively, while the r.m.s. deviation for the phenyl (C1–C6), benzyl (C14–C19) and cyclohexyl (C7–C12) rings are 0.0021, 0.0036 and 0.2365 Å, respectively. An intramolecular C—H···O hydrogen bond gives rise to a five-membered hydrogen bonded ring (Table 1).

Related literature top

For the biological activity of sulfonamides, see: Innocenti et al. (2004); Ozbek et al. (2007); Parari et al. (2008); Ratish et al. (2009); Selnam et al. (2001); For related structures, see: Khan et al. (2009); Zia-ur-Rehman et al. (2009) Gowda et al. (2007a,b,c). For bond length data, see: Allen et al. (1987).

Experimental top

A mixture of N-cyclohexylbenzene sulfonamide (1 g, 0.43 mmol), sodium hydride (0.21 g, 0.88 mmol) and N, N-dimethylformamide (10 ml) was stirred at room temperature for half an hour followed by addition of benzyl chloride (0.114 g, 0.90 mmol). Stirring was continued further for a period of three hours and the contents were poured over crushed ice. Precipitated product was isolated, washed and crystallized from methanol-water mixture (50:50).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and local programs.

Figures top

Fig. 1. The molecular structure of (I), with displacement ellipsoids at the 50% probability level.

N-Benzyl-N-cyclohexylbenzenesulfonamide top

Crystal data top

C₁₉H₂₃NO₂S	F(000) = 704
M_r = 329.44	D_x = 1.253 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3979 reflections
a = 9.1996 (5) Å	θ = 2.3–21.8°
b = 11.0406 (5) Å	µ = 0.20 mm⁻¹
c = 17.1897 (9) Å	T = 296 K
V = 1745.94 (15) Å³	Blocks, colourless
Z = 4	0.39 × 0.34 × 0.28 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	4306 independent reflections
Radiation source: fine-focus sealed tube	3507 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ϕ and ω scans	θ_max = 28.3°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→11
T_min = 0.928, T_max = 0.948	k = −11→14
10897 measured reflections	l = −22→17

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-atom parameters constrained
wR(F²) = 0.094	w = 1/[σ²(F_o²) + (0.049P)² + 0.1094P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
4306 reflections	Δρ_max = 0.24 e Å⁻³
208 parameters	Δρ_min = −0.24 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1853 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.03 (7)

Crystal data top

C₁₉H₂₃NO₂S	V = 1745.94 (15) Å³
M_r = 329.44	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 9.1996 (5) Å	µ = 0.20 mm⁻¹
b = 11.0406 (5) Å	T = 296 K
c = 17.1897 (9) Å	0.39 × 0.34 × 0.28 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	4306 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3507 reflections with I > 2σ(I)
T_min = 0.928, T_max = 0.948	R_int = 0.023
10897 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	H-atom parameters constrained
wR(F²) = 0.094	Δρ_max = 0.24 e Å⁻³
S = 1.03	Δρ_min = −0.24 e Å⁻³
4306 reflections	Absolute structure: Flack (1983), 1853 Friedel pairs
208 parameters	Absolute structure parameter: 0.03 (7)
0 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
C1	0.3444 (2)	0.27298 (15)	0.91369 (9)	0.0423 (4)
C2	0.4528 (2)	0.2866 (2)	0.96899 (11)	0.0596 (5)
H2	0.5302	0.2325	0.9709	0.072*
C3	0.4447 (3)	0.3813 (2)	1.02106 (13)	0.0737 (7)
H3	0.5170	0.3910	1.0583	0.088*
C4	0.3305 (3)	0.4615 (2)	1.01838 (13)	0.0720 (7)
H4	0.3252	0.5250	1.0539	0.086*
C5	0.2244 (3)	0.4475 (2)	0.96314 (14)	0.0676 (6)
H5	0.1478	0.5023	0.9611	0.081*
C6	0.2295 (2)	0.3532 (2)	0.91061 (11)	0.0542 (5)
H6	0.1566	0.3438	0.8736	0.065*
C7	0.61067 (18)	0.20568 (15)	0.77713 (10)	0.0396 (4)
H7	0.6361	0.1620	0.8249	0.048*
C8	0.6733 (2)	0.33204 (18)	0.78485 (14)	0.0587 (5)
H8A	0.6285	0.3732	0.8286	0.070*
H8B	0.6528	0.3782	0.7381	0.070*
C9	0.8375 (2)	0.3243 (2)	0.79731 (14)	0.0647 (6)
H9A	0.8777	0.4054	0.8002	0.078*
H9B	0.8572	0.2838	0.8463	0.078*
C10	0.9099 (2)	0.2560 (2)	0.73209 (13)	0.0653 (6)
H10A	0.8985	0.3008	0.6839	0.078*
H10B	1.0131	0.2489	0.7428	0.078*
C11	0.8458 (2)	0.1321 (2)	0.72278 (14)	0.0717 (6)
H11A	0.8666	0.0845	0.7689	0.086*
H11B	0.8908	0.0922	0.6787	0.086*
C12	0.6807 (2)	0.13740 (19)	0.71029 (12)	0.0574 (5)
H12A	0.6593	0.1780	0.6616	0.069*
H12B	0.6416	0.0559	0.7077	0.069*
C13	0.3750 (2)	0.28365 (15)	0.71472 (9)	0.0407 (4)
H13A	0.4319	0.3571	0.7088	0.049*
H13B	0.2811	0.3064	0.7358	0.049*
C14	0.35265 (19)	0.22767 (13)	0.63549 (9)	0.0385 (3)
C15	0.2610 (2)	0.12964 (17)	0.62532 (12)	0.0556 (5)
H15	0.2141	0.0962	0.6681	0.067*
C16	0.2385 (3)	0.0808 (2)	0.55228 (14)	0.0647 (6)
H16	0.1760	0.0153	0.5463	0.078*
C17	0.3074 (3)	0.1283 (2)	0.48873 (12)	0.0646 (6)
H17	0.2917	0.0955	0.4396	0.077*
C18	0.4001 (3)	0.2249 (2)	0.49795 (12)	0.0668 (6)
H18	0.4484	0.2568	0.4551	0.080*
C19	0.4216 (2)	0.27463 (17)	0.57071 (11)	0.0535 (5)
H19	0.4833	0.3407	0.5762	0.064*
N1	0.44909 (16)	0.20318 (12)	0.77103 (8)	0.0402 (3)
O1	0.21214 (15)	0.12969 (13)	0.81853 (8)	0.0590 (4)
O2	0.43915 (17)	0.05891 (11)	0.88027 (8)	0.0592 (4)
S1	0.35656 (5)	0.15399 (4)	0.84502 (2)	0.04355 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0453 (9)	0.0462 (9)	0.0352 (8)	−0.0024 (8)	0.0063 (8)	0.0056 (7)
C2	0.0564 (12)	0.0720 (13)	0.0504 (11)	0.0075 (11)	−0.0061 (10)	0.0019 (10)
C3	0.0780 (16)	0.0892 (17)	0.0539 (12)	−0.0098 (14)	−0.0089 (12)	−0.0100 (12)
C4	0.0928 (19)	0.0669 (13)	0.0564 (12)	−0.0073 (14)	0.0093 (14)	−0.0126 (11)
C5	0.0761 (15)	0.0617 (13)	0.0651 (14)	0.0124 (12)	0.0139 (12)	−0.0008 (11)
C6	0.0508 (11)	0.0621 (11)	0.0495 (10)	0.0073 (10)	0.0009 (8)	0.0008 (10)
C7	0.0378 (9)	0.0447 (9)	0.0364 (8)	0.0043 (7)	−0.0017 (7)	0.0039 (7)
C8	0.0437 (11)	0.0513 (10)	0.0812 (14)	0.0000 (9)	0.0033 (10)	−0.0147 (10)
C9	0.0432 (11)	0.0695 (13)	0.0815 (14)	−0.0033 (10)	−0.0042 (10)	−0.0146 (12)
C10	0.0351 (10)	0.0957 (17)	0.0651 (13)	0.0074 (11)	−0.0003 (9)	−0.0016 (13)
C11	0.0513 (12)	0.0869 (16)	0.0768 (14)	0.0229 (13)	0.0006 (11)	−0.0247 (13)
C12	0.0501 (11)	0.0611 (11)	0.0610 (12)	0.0101 (9)	−0.0006 (9)	−0.0166 (10)
C13	0.0418 (9)	0.0388 (8)	0.0416 (9)	0.0036 (7)	−0.0034 (7)	0.0009 (7)
C14	0.0357 (8)	0.0376 (7)	0.0423 (8)	0.0045 (7)	−0.0080 (7)	0.0032 (6)
C15	0.0549 (11)	0.0551 (11)	0.0570 (11)	−0.0136 (10)	−0.0014 (9)	0.0008 (9)
C16	0.0671 (14)	0.0558 (11)	0.0712 (14)	−0.0153 (11)	−0.0111 (11)	−0.0097 (11)
C17	0.0855 (16)	0.0613 (12)	0.0469 (11)	0.0000 (11)	−0.0204 (11)	−0.0056 (10)
C18	0.0957 (18)	0.0657 (14)	0.0390 (10)	−0.0094 (13)	−0.0041 (10)	0.0078 (10)
C19	0.0662 (13)	0.0471 (10)	0.0472 (11)	−0.0115 (10)	−0.0069 (9)	0.0067 (9)
N1	0.0387 (8)	0.0455 (8)	0.0365 (7)	0.0043 (6)	−0.0002 (6)	0.0043 (6)
O1	0.0469 (7)	0.0690 (9)	0.0610 (8)	−0.0151 (7)	0.0052 (6)	−0.0039 (7)
O2	0.0711 (9)	0.0436 (7)	0.0629 (8)	0.0059 (7)	0.0071 (7)	0.0168 (6)
S1	0.0449 (2)	0.0415 (2)	0.0442 (2)	−0.0025 (2)	0.0035 (2)	0.00529 (19)

Geometric parameters (Å, º) top

C1—C6	1.380 (3)	C10—H10B	0.9700
C1—C2	1.386 (3)	C11—C12	1.535 (3)
C1—S1	1.7696 (18)	C11—H11A	0.9700
C2—C3	1.378 (3)	C11—H11B	0.9700
C2—H2	0.9300	C12—H12A	0.9700
C3—C4	1.375 (3)	C12—H12B	0.9700
C3—H3	0.9300	C13—N1	1.480 (2)
C4—C5	1.370 (3)	C13—C14	1.510 (2)
C4—H4	0.9300	C13—H13A	0.9700
C5—C6	1.379 (3)	C13—H13B	0.9700
C5—H5	0.9300	C14—C19	1.382 (2)
C6—H6	0.9300	C14—C15	1.383 (2)
C7—N1	1.490 (2)	C15—C16	1.382 (3)
C7—C8	1.515 (3)	C15—H15	0.9300
C7—C12	1.518 (2)	C16—C17	1.368 (3)
C7—H7	0.9800	C16—H16	0.9300
C8—C9	1.528 (3)	C17—C18	1.374 (3)
C8—H8A	0.9700	C17—H17	0.9300
C8—H8B	0.9700	C18—C19	1.380 (3)
C9—C10	1.506 (3)	C18—H18	0.9300
C9—H9A	0.9700	C19—H19	0.9300
C9—H9B	0.9700	N1—S1	1.6240 (14)
C10—C11	1.498 (3)	O1—S1	1.4299 (14)
C10—H10A	0.9700	O2—S1	1.4305 (14)

C6—C1—C2	120.51 (18)	C12—C11—H11A	109.3
C6—C1—S1	119.94 (14)	C10—C11—H11B	109.3
C2—C1—S1	119.54 (15)	C12—C11—H11B	109.3
C3—C2—C1	119.3 (2)	H11A—C11—H11B	107.9
C3—C2—H2	120.4	C7—C12—C11	109.44 (16)
C1—C2—H2	120.4	C7—C12—H12A	109.8
C4—C3—C2	120.6 (2)	C11—C12—H12A	109.8
C4—C3—H3	119.7	C7—C12—H12B	109.8
C2—C3—H3	119.7	C11—C12—H12B	109.8
C5—C4—C3	119.6 (2)	H12A—C12—H12B	108.2
C5—C4—H4	120.2	N1—C13—C14	114.01 (13)
C3—C4—H4	120.2	N1—C13—H13A	108.7
C4—C5—C6	121.0 (2)	C14—C13—H13A	108.7
C4—C5—H5	119.5	N1—C13—H13B	108.7
C6—C5—H5	119.5	C14—C13—H13B	108.7
C5—C6—C1	119.05 (19)	H13A—C13—H13B	107.6
C5—C6—H6	120.5	C19—C14—C15	118.11 (16)
C1—C6—H6	120.5	C19—C14—C13	120.72 (15)
N1—C7—C8	113.74 (14)	C15—C14—C13	121.17 (16)
N1—C7—C12	111.15 (15)	C16—C15—C14	120.77 (19)
C8—C7—C12	111.24 (15)	C16—C15—H15	119.6
N1—C7—H7	106.8	C14—C15—H15	119.6
C8—C7—H7	106.8	C17—C16—C15	120.4 (2)
C12—C7—H7	106.8	C17—C16—H16	119.8
C7—C8—C9	109.69 (17)	C15—C16—H16	119.8
C7—C8—H8A	109.7	C16—C17—C18	119.5 (2)
C9—C8—H8A	109.7	C16—C17—H17	120.2
C7—C8—H8B	109.7	C18—C17—H17	120.2
C9—C8—H8B	109.7	C17—C18—C19	120.1 (2)
H8A—C8—H8B	108.2	C17—C18—H18	119.9
C10—C9—C8	111.14 (18)	C19—C18—H18	119.9
C10—C9—H9A	109.4	C18—C19—C14	121.02 (18)
C8—C9—H9A	109.4	C18—C19—H19	119.5
C10—C9—H9B	109.4	C14—C19—H19	119.5
C8—C9—H9B	109.4	C13—N1—C7	119.61 (14)
H9A—C9—H9B	108.0	C13—N1—S1	118.13 (12)
C11—C10—C9	111.26 (19)	C7—N1—S1	118.29 (11)
C11—C10—H10A	109.4	O1—S1—O2	119.39 (9)
C9—C10—H10A	109.4	O1—S1—N1	107.48 (8)
C11—C10—H10B	109.4	O2—S1—N1	107.38 (8)
C9—C10—H10B	109.4	O1—S1—C1	107.04 (9)
H10A—C10—H10B	108.0	O2—S1—C1	107.20 (8)
C10—C11—C12	111.71 (18)	N1—S1—C1	107.90 (7)
C10—C11—H11A	109.3

C6—C1—C2—C3	0.1 (3)	C16—C17—C18—C19	−1.0 (4)
S1—C1—C2—C3	178.36 (17)	C17—C18—C19—C14	1.0 (3)
C1—C2—C3—C4	0.0 (3)	C15—C14—C19—C18	−0.2 (3)
C2—C3—C4—C5	−0.4 (4)	C13—C14—C19—C18	−179.12 (19)
C3—C4—C5—C6	0.7 (4)	C14—C13—N1—C7	90.42 (18)
C4—C5—C6—C1	−0.6 (3)	C14—C13—N1—S1	−112.35 (15)
C2—C1—C6—C5	0.3 (3)	C8—C7—N1—C13	49.3 (2)
S1—C1—C6—C5	−178.03 (16)	C12—C7—N1—C13	−77.18 (18)
N1—C7—C8—C9	175.43 (16)	C8—C7—N1—S1	−107.91 (16)
C12—C7—C8—C9	−58.1 (2)	C12—C7—N1—S1	125.63 (14)
C7—C8—C9—C10	56.9 (2)	C13—N1—S1—O1	37.74 (14)
C8—C9—C10—C11	−56.2 (3)	C7—N1—S1—O1	−164.73 (12)
C9—C10—C11—C12	55.8 (3)	C13—N1—S1—O2	167.36 (12)
N1—C7—C12—C11	−174.82 (17)	C7—N1—S1—O2	−35.11 (15)
C8—C7—C12—C11	57.3 (2)	C13—N1—S1—C1	−77.38 (14)
C10—C11—C12—C7	−56.0 (3)	C7—N1—S1—C1	80.15 (14)
N1—C13—C14—C19	−115.08 (18)	C6—C1—S1—O1	−25.17 (17)
N1—C13—C14—C15	66.1 (2)	C2—C1—S1—O1	156.51 (15)
C19—C14—C15—C16	−0.5 (3)	C6—C1—S1—O2	−154.38 (14)
C13—C14—C15—C16	178.40 (19)	C2—C1—S1—O2	27.30 (17)
C14—C15—C16—C17	0.5 (3)	C6—C1—S1—N1	90.25 (16)
C15—C16—C17—C18	0.3 (4)	C2—C1—S1—N1	−88.07 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O2	0.98	2.34	2.874 (2)	113

Experimental details

Crystal data
Chemical formula	C₁₉H₂₃NO₂S
M_r	329.44
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	296
a, b, c (Å)	9.1996 (5), 11.0406 (5), 17.1897 (9)
V (Å³)	1745.94 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.39 × 0.34 × 0.28

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.928, 0.948
No. of measured, independent and observed [I > 2σ(I)] reflections	10897, 4306, 3507
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.666

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.094, 1.03
No. of reflections	4306
No. of parameters	208
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.24
Absolute structure	Flack (1983), 1853 Friedel pairs
Absolute structure parameter	0.03 (7)

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and Mercury (Macrae et al., 2006), SHELXTL (Sheldrick, 2008) and local programs.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O2	0.98	2.34	2.874 (2)	113

Acknowledgements

The authors are grateful to the Higher Education Commission of Pakistan for the financial support to purchase the diffractometer.

References

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