N-Ethyl-N-(2-meth­oxy­phen­yl)benzene­sulfonamide

Aziz-ur-Rehman; Rafique, H.; Akkurt, M.; Dilber, N.; Abbasi, M.A.; Khan, I.U.

doi:10.1107/S1600536810023287

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1728

doi:10.1107/S1600536810023287

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N-Ethyl-N-(2-methoxyphenyl)benzenesulfonamide

Aziz-ur-Rehman,^a ‡ Humaira Rafique,^a Mehmet Akkurt,^b ^* Nabila Dilber,^a Muhammad Athar Abbasi ^a and Islam Ullah Khan ^a

^aDepartment of Chemistry, Government College University, Lahore 54000, Pakistan, and ^bDepartment of Physics, Faculty of Arts and Sciences, Erciyes University, 38039 Kayseri, Turkey
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 15 June 2010; accepted 16 June 2010; online 23 June 2010)

In the title molecule, C₁₅H₁₇NO₃S, the C—S—N—C_benzene torsion angle is 81.45 (16)°, and the two aromatic rings form a dihedral angle of 45.83 (12)°. In the crystal structure, weak intermolecular C—H⋯O hydrogen bonds link the molecules into chains parallel to the b axis.

Related literature

For the biological activity of sulfonamides, see: Ozbek et al. (2007 ); Parari et al. (2008 ). For related structures, see: Mariam et al. (2009 ); Arshad et al. (2009 ); Asiri et al. (2009 ); Khan et al. (2010 ); Akkurt et al. (2010a ,b ).

Experimental

Crystal data

C₁₅H₁₇NO₃S
M_r = 291.37
Monoclinic, P 2₁ /c
a = 9.3098 (5) Å
b = 9.5664 (6) Å
c = 17.1949 (10) Å
β = 104.040 (2)°
V = 1485.65 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 296 K
0.15 × 0.10 × 0.06 mm

Data collection

Bruker APEXII CCD diffractometer
13197 measured reflections
3670 independent reflections
1963 reflections with I > 2σ(I)
R_int = 0.045

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.157
S = 0.99
3670 reflections
183 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O2ⁱ	0.93	2.53	3.300 (3)	140
Symmetry code: (i) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810023287/cv2735sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810023287/cv2735Isup2.hkl

checkCIF report

Comment top

Sulfonamides are known as biologically active compounds (Ozbek et al., 2007; Parari et al., 2008). As a contribution to a structural study of sulfonamide derivatives (Mariam et al., 2009; Arshad et al., 2009; Asiri et al., 2009; Khan et al., 2010; Akkurt et al., 2010a,b) we present here the title compound, (I).

The title molecule (Fig. 1) is bent at the S atoms with the C1—S1—N1—C9 torsion angle of 81.45 (16)°. The dihedral angle between the phenyl (C1–C6) and benzene (C9–C14) rings is 45.83 (12)°.

In the crystal structure of (I), weak intermolecular C—H···O hydrogen bonds (Table 1) link the molecules into chains parallel to b axis.

Related literature top

For the biological activity of sulfonamides, see: Ozbek et al. (2007); Parari et al. (2008). For related structures, see: Mariam et al. (2009); Arshad et al. (2009\bbr00); Asiri et al. (2009); Khan et al. (2010); Akkurt et al. (2010a,b).

Experimental top

A mixture of N-(2-methoxyphenyl)benzenesulfonamide (1.24 g, 5.0 mmol), sodium hydride (0.24 g, 10 mmol) and N,N-dimethylformamide (10 ml) was stirred at room temperature for 30 min and then ethyl iodide (0.4 ml, 5.0 mmol) was added. The stirring was continued further for a period of 3 h and the contents were poured over crushed ice. The precipitated product was isolated, washed and re-crystallized from methanolic solution. It was crystallized by slow evaporation of the solvent. Yield 72%.

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: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

Fig. 1. Molecular structure of (I) showing the atom labelling scheme, Displacement ellipsoids are drawn at the 30% probability level.

N-Ethyl-N-(2-methoxyphenyl)benzenesulfonamide top

Crystal data top

C₁₅H₁₇NO₃S	F(000) = 616
M_r = 291.37	D_x = 1.303 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3431 reflections
a = 9.3098 (5) Å	θ = 2.3–24.5°
b = 9.5664 (6) Å	µ = 0.22 mm⁻¹
c = 17.1949 (10) Å	T = 296 K
β = 104.040 (2)°	Block, colourless
V = 1485.65 (15) Å³	0.15 × 0.10 × 0.06 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	1963 reflections with I > 2σ(I)
Radiation source: sealed tube	R_int = 0.045
Graphite monochromator	θ_max = 28.3°, θ_min = 3.1°
ϕ and ω scans	h = −12→10
13197 measured reflections	k = −11→12
3670 independent reflections	l = −20→22

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.157	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0842P)²] where P = (F_o² + 2F_c²)/3
3670 reflections	(Δ/σ)_max < 0.001
183 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₁₅H₁₇NO₃S	V = 1485.65 (15) Å³
M_r = 291.37	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.3098 (5) Å	µ = 0.22 mm⁻¹
b = 9.5664 (6) Å	T = 296 K
c = 17.1949 (10) Å	0.15 × 0.10 × 0.06 mm
β = 104.040 (2)°

Data collection top

Bruker APEXII CCD diffractometer	1963 reflections with I > 2σ(I)
13197 measured reflections	R_int = 0.045
3670 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.157	H-atom parameters constrained
S = 0.99	Δρ_max = 0.30 e Å⁻³
3670 reflections	Δρ_min = −0.27 e Å⁻³
183 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 e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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	0.86267 (6)	0.81474 (6)	0.18075 (4)	0.0619 (2)
O1	0.99631 (18)	0.7591 (2)	0.16733 (12)	0.0964 (8)
O2	0.81194 (19)	0.94809 (17)	0.14864 (9)	0.0771 (7)
O3	0.57342 (18)	0.66902 (16)	0.25621 (9)	0.0675 (6)
N1	0.73281 (18)	0.70249 (17)	0.14324 (10)	0.0532 (6)
C1	0.8828 (2)	0.8200 (2)	0.28471 (13)	0.0557 (7)
C2	0.8216 (3)	0.9285 (2)	0.31844 (14)	0.0687 (9)
C3	0.8335 (3)	0.9308 (3)	0.39875 (16)	0.0899 (11)
C4	0.9055 (4)	0.8251 (4)	0.44612 (18)	0.1036 (15)
C5	0.9646 (4)	0.7163 (4)	0.4127 (2)	0.1047 (14)
C6	0.9558 (3)	0.7136 (3)	0.33214 (17)	0.0809 (10)
C7	0.7640 (3)	0.5514 (2)	0.15704 (15)	0.0723 (9)
C8	0.6825 (4)	0.4652 (3)	0.09012 (17)	0.1080 (13)
C9	0.5821 (2)	0.7500 (2)	0.12968 (11)	0.0476 (7)
C10	0.5011 (2)	0.7321 (2)	0.18716 (12)	0.0498 (7)
C11	0.3558 (2)	0.7784 (2)	0.17143 (14)	0.0633 (9)
C12	0.2933 (3)	0.8395 (2)	0.09883 (17)	0.0740 (10)
C13	0.3707 (3)	0.8566 (2)	0.04225 (15)	0.0722 (9)
C14	0.5157 (3)	0.8111 (2)	0.05732 (13)	0.0605 (8)
C15	0.5112 (3)	0.6721 (3)	0.32343 (15)	0.0878 (11)
H2	0.77210	1.00010	0.28620	0.0820*
H3	0.79260	1.00430	0.42150	0.1080*
H4	0.91440	0.82730	0.50120	0.1240*
H5	1.01110	0.64350	0.44500	0.1260*
H6	0.99860	0.64090	0.30970	0.0970*
H7A	0.86930	0.53530	0.16450	0.0870*
H7B	0.73710	0.52310	0.20580	0.0870*
H8A	0.57950	0.46310	0.09050	0.1620*
H8B	0.72140	0.37180	0.09570	0.1620*
H8C	0.69320	0.50430	0.04040	0.1620*
H11	0.30120	0.76820	0.20970	0.0760*
H12	0.19550	0.86980	0.08830	0.0890*
H13	0.32660	0.89860	−0.00640	0.0870*
H14	0.56880	0.82170	0.01840	0.0730*
H15A	0.47490	0.76430	0.32950	0.1320*
H15B	0.58550	0.64750	0.37070	0.1320*
H15C	0.43090	0.60650	0.31570	0.1320*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0444 (4)	0.0686 (4)	0.0765 (4)	−0.0128 (3)	0.0219 (3)	−0.0093 (3)
O1	0.0473 (10)	0.1239 (15)	0.1290 (16)	−0.0121 (10)	0.0426 (10)	−0.0311 (12)
O2	0.0798 (12)	0.0655 (11)	0.0836 (11)	−0.0281 (9)	0.0152 (8)	0.0088 (8)
O3	0.0664 (10)	0.0780 (11)	0.0630 (10)	0.0078 (8)	0.0252 (8)	0.0158 (7)
N1	0.0449 (10)	0.0534 (11)	0.0631 (11)	−0.0040 (8)	0.0167 (8)	−0.0081 (8)
C1	0.0362 (11)	0.0496 (12)	0.0761 (15)	−0.0024 (9)	0.0033 (10)	−0.0073 (10)
C2	0.0755 (17)	0.0528 (14)	0.0751 (16)	0.0057 (12)	0.0132 (12)	−0.0031 (11)
C3	0.111 (2)	0.0808 (19)	0.0776 (19)	0.0022 (17)	0.0224 (16)	−0.0168 (15)
C4	0.127 (3)	0.106 (3)	0.0640 (17)	−0.010 (2)	−0.0037 (17)	−0.0083 (16)
C5	0.110 (3)	0.089 (2)	0.087 (2)	0.0113 (18)	−0.0303 (18)	0.0097 (17)
C6	0.0691 (17)	0.0680 (16)	0.089 (2)	0.0152 (13)	−0.0131 (14)	−0.0081 (13)
C7	0.0600 (15)	0.0580 (15)	0.1008 (18)	0.0077 (11)	0.0233 (13)	−0.0162 (12)
C8	0.143 (3)	0.0672 (18)	0.122 (2)	−0.0313 (18)	0.048 (2)	−0.0282 (16)
C9	0.0446 (12)	0.0434 (11)	0.0553 (12)	−0.0076 (9)	0.0130 (9)	−0.0070 (9)
C10	0.0464 (12)	0.0459 (11)	0.0576 (12)	−0.0058 (9)	0.0135 (9)	−0.0012 (9)
C11	0.0455 (13)	0.0638 (14)	0.0839 (17)	−0.0052 (10)	0.0224 (11)	−0.0003 (12)
C12	0.0492 (14)	0.0662 (16)	0.099 (2)	0.0021 (11)	0.0035 (13)	0.0004 (13)
C13	0.0691 (18)	0.0655 (15)	0.0701 (16)	−0.0038 (12)	−0.0059 (13)	0.0066 (12)
C14	0.0645 (15)	0.0628 (14)	0.0537 (13)	−0.0128 (11)	0.0132 (11)	−0.0029 (10)
C15	0.093 (2)	0.110 (2)	0.0686 (17)	−0.0052 (17)	0.0353 (14)	0.0107 (14)

Geometric parameters (Å, º) top

S1—O1	1.4226 (19)	C12—C13	1.354 (4)
S1—O2	1.4243 (17)	C13—C14	1.382 (4)
S1—N1	1.6286 (18)	C2—H2	0.9300
S1—C1	1.752 (2)	C3—H3	0.9300
O3—C10	1.356 (2)	C4—H4	0.9300
O3—C15	1.413 (3)	C5—H5	0.9300
N1—C7	1.482 (3)	C6—H6	0.9300
N1—C9	1.439 (3)	C7—H7A	0.9700
C1—C2	1.378 (3)	C7—H7B	0.9700
C1—C6	1.376 (3)	C8—H8A	0.9600
C2—C3	1.359 (4)	C8—H8B	0.9600
C3—C4	1.368 (5)	C8—H8C	0.9600
C4—C5	1.367 (5)	C11—H11	0.9300
C5—C6	1.368 (4)	C12—H12	0.9300
C7—C8	1.468 (4)	C13—H13	0.9300
C9—C10	1.392 (3)	C14—H14	0.9300
C9—C14	1.378 (3)	C15—H15A	0.9600
C10—C11	1.386 (3)	C15—H15B	0.9600
C11—C12	1.373 (4)	C15—H15C	0.9600

O1···C11ⁱ	3.336 (3)	C11···H15A	2.6800
O1···C12ⁱ	3.347 (3)	C11···H15C	2.9200
O2···C6ⁱⁱ	3.300 (3)	C15···H11	2.5800
O2···C14	3.113 (3)	H2···O2	2.5300
O3···N1	2.734 (2)	H2···C11^v	3.0800
O3···C2	3.383 (3)	H2···H15C^v	2.4600
O3···C7	2.965 (3)	H3···H8C^viii	2.4400
O3···C1	3.152 (3)	H4···O1^viii	2.8900
O1···H11ⁱ	2.7600	H6···O1	2.6900
O1···H7A	2.4400	H6···O2^vi	2.5300
O1···H4ⁱⁱⁱ	2.8900	H7A···O1	2.4400
O1···H12ⁱ	2.7600	H7A···C1^vi	3.0600
O1···H6	2.6900	H7A···C2^vi	3.0000
O2···H13^iv	2.8800	H7B···O3	2.3800
O2···H15C^v	2.9100	H7B···C10	2.9300
O2···H2	2.5300	H8A···C9	2.8200
O2···H6ⁱⁱ	2.5300	H8A···H15A^ix	2.4700
O3···H7B	2.3800	H8C···C3ⁱⁱⁱ	3.0900
N1···O3	2.734 (2)	H8C···H3ⁱⁱⁱ	2.4400
C1···O3	3.152 (3)	H11···O1^vii	2.7600
C2···O3	3.383 (3)	H11···C15	2.5800
C6···O2^vi	3.300 (3)	H11···H15A	2.2900
C6···C7	3.472 (4)	H11···H15C	2.4700
C7···C6	3.472 (4)	H12···O1^vii	2.7600
C7···O3	2.965 (3)	H13···O2^iv	2.8800
C11···O1^vii	3.336 (3)	H14···H15Bⁱⁱⁱ	2.6000
C12···O1^vii	3.347 (3)	H15A···C11	2.6800
C14···O2	3.113 (3)	H15A···H11	2.2900
C1···H7Aⁱⁱ	3.0600	H15A···C8^v	2.9600
C2···H7Aⁱⁱ	3.0000	H15A···H8A^v	2.4700
C3···H8C^viii	3.0900	H15B···H14^viii	2.6000
C8···H15A^ix	2.9600	H15C···C11	2.9200
C9···H8A	2.8200	H15C···H11	2.4700
C10···H7B	2.9300	H15C···O2^ix	2.9100
C11···H2^ix	3.0800	H15C···H2^ix	2.4600

O1—S1—O2	119.54 (11)	C4—C3—H3	120.00
O1—S1—N1	106.47 (10)	C3—C4—H4	120.00
O1—S1—C1	107.15 (11)	C5—C4—H4	120.00
O2—S1—N1	107.01 (10)	C4—C5—H5	120.00
O2—S1—C1	108.24 (10)	C6—C5—H5	120.00
N1—S1—C1	107.96 (9)	C1—C6—H6	120.00
C10—O3—C15	119.46 (18)	C5—C6—H6	120.00
S1—N1—C7	118.81 (15)	N1—C7—H7A	109.00
S1—N1—C9	117.18 (13)	N1—C7—H7B	109.00
C7—N1—C9	118.65 (18)	C8—C7—H7A	109.00
S1—C1—C2	119.88 (16)	C8—C7—H7B	109.00
S1—C1—C6	119.90 (18)	H7A—C7—H7B	108.00
C2—C1—C6	120.2 (2)	C7—C8—H8A	109.00
C1—C2—C3	120.0 (2)	C7—C8—H8B	109.00
C2—C3—C4	120.1 (3)	C7—C8—H8C	109.00
C3—C4—C5	120.1 (3)	H8A—C8—H8B	109.00
C4—C5—C6	120.6 (3)	H8A—C8—H8C	109.00
C1—C6—C5	119.1 (3)	H8B—C8—H8C	109.00
N1—C7—C8	112.2 (2)	C10—C11—H11	120.00
N1—C9—C10	121.41 (17)	C12—C11—H11	120.00
N1—C9—C14	119.11 (19)	C11—C12—H12	119.00
C10—C9—C14	119.5 (2)	C13—C12—H12	119.00
O3—C10—C9	115.92 (17)	C12—C13—H13	120.00
O3—C10—C11	124.52 (19)	C14—C13—H13	120.00
C9—C10—C11	119.56 (19)	C9—C14—H14	120.00
C10—C11—C12	119.4 (2)	C13—C14—H14	120.00
C11—C12—C13	121.5 (2)	O3—C15—H15A	109.00
C12—C13—C14	119.6 (2)	O3—C15—H15B	109.00
C9—C14—C13	120.5 (2)	O3—C15—H15C	109.00
C1—C2—H2	120.00	H15A—C15—H15B	109.00
C3—C2—H2	120.00	H15A—C15—H15C	109.00
C2—C3—H3	120.00	H15B—C15—H15C	109.00

O1—S1—N1—C7	42.39 (19)	S1—C1—C2—C3	178.2 (2)
O1—S1—N1—C9	−163.78 (15)	C6—C1—C2—C3	0.1 (4)
O2—S1—N1—C7	171.30 (16)	S1—C1—C6—C5	−177.1 (2)
O2—S1—N1—C9	−34.87 (17)	C2—C1—C6—C5	1.0 (4)
C1—S1—N1—C7	−72.39 (18)	C1—C2—C3—C4	−0.4 (4)
C1—S1—N1—C9	81.45 (16)	C2—C3—C4—C5	−0.5 (5)
O1—S1—C1—C2	144.01 (19)	C3—C4—C5—C6	1.7 (6)
O1—S1—C1—C6	−38.0 (2)	C4—C5—C6—C1	−1.9 (5)
O2—S1—C1—C2	13.9 (2)	N1—C9—C10—O3	0.7 (3)
O2—S1—C1—C6	−168.12 (19)	N1—C9—C10—C11	−179.48 (18)
N1—S1—C1—C2	−101.66 (19)	C14—C9—C10—O3	178.90 (18)
N1—S1—C1—C6	76.4 (2)	C14—C9—C10—C11	−1.2 (3)
C15—O3—C10—C9	167.2 (2)	N1—C9—C14—C13	179.41 (18)
C15—O3—C10—C11	−12.7 (3)	C10—C9—C14—C13	1.1 (3)
S1—N1—C7—C8	−148.4 (2)	O3—C10—C11—C12	−179.24 (19)
C9—N1—C7—C8	58.1 (3)	C9—C10—C11—C12	0.9 (3)
S1—N1—C9—C10	−93.0 (2)	C10—C11—C12—C13	−0.5 (3)
S1—N1—C9—C14	88.8 (2)	C11—C12—C13—C14	0.4 (3)
C7—N1—C9—C10	60.9 (3)	C12—C13—C14—C9	−0.7 (3)
C7—N1—C9—C14	−117.4 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2	0.93	2.53	2.905 (3)	104
C6—H6···O2^vi	0.93	2.53	3.300 (3)	140
C7—H7A···O1	0.97	2.44	2.911 (3)	109
C7—H7B···O3	0.97	2.38	2.965 (3)	118

Symmetry code: (vi) −x+2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₇NO₃S
M_r	291.37
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	9.3098 (5), 9.5664 (6), 17.1949 (10)
β (°)	104.040 (2)
V (Å³)	1485.65 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.15 × 0.10 × 0.06

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	13197, 3670, 1963
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.157, 0.99
No. of reflections	3670
No. of parameters	183
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.27

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), 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
C6—H6···O2ⁱ	0.93	2.53	3.300 (3)	140

Symmetry code: (i) −x+2, y−1/2, −z+1/2.

Footnotes

‡Additional corresponding author, e-mail: azizhej@hotmail.com.

Acknowledgements

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

References

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