N-Benzyl-N,4-dimethyl­benzene­sulfonamide

Khan, I.U.; Akkurt, M.; Sharif, S.; Ahmad, W.

doi:10.1107/S1600536810044156

organic compounds

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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page o3053

https://doi.org/10.1107/S1600536810044156

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N-Benzyl-N,4-dimethylbenzenesulfonamide

Islam Ullah Khan,^a Mehmet Akkurt,^b ^* Shahzad Sharif ^a and Waqar Ahmad ^a

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

(Received 27 October 2010; accepted 28 October 2010; online 6 November 2010)

The molecule of the title compound, C₁₅H₁₇NO₂S, has a C—S—N—C torsion angle of 71.4 (2)°, and the dihedral angle between the benzene rings is 82.83 (16)°. In the crystal, molecules are linked into chains along the b axis via C—H⋯O hydrogen bonds. A C—H⋯π interaction is also present in the crystal structure.

Related literature

For the pharmacological activities of sulfonamides, see: Maren (1976 ); Boyd (1988 ). For our previous studies on derivatives of sulfonamide, see: Khan, Ahmad, Arshad et al. (2010 ); Khan, Ahmad, Sharif et al. (2010 ).

Experimental

Crystal data

C₁₅H₁₇NO₂S
M_r = 275.37
Monoclinic, P 2₁ /c
a = 15.0386 (16) Å
b = 8.2632 (7) Å
c = 12.0758 (12) Å
β = 105.902 (4)°
V = 1443.2 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 296 K
0.28 × 0.17 × 0.09 mm

Data collection

Bruker APEXII CCD diffractometer
13504 measured reflections
3569 independent reflections
1580 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.155
S = 1.01
3569 reflections
174 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C10–C15 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1ⁱ	0.93	2.53	3.414 (3)	158
C9—H9A⋯Cg2ⁱⁱ	0.97	2.99	3.721 (3)	133
Symmetry codes: (i) x, y-1, z; (ii) -x, -y, -z+1.

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: https://doi.org/10.1107/S1600536810044156/xu5070sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810044156/xu5070Isup2.hkl

checkCIF report

Comment top

Sulfonamides have extensively been reported for their wide variety of pharmacological activities such as antibacterial (Maren, 1976) and diuretic (Boyd, 1988). The present structure is continuous to our previous reported derivative of sulfonamide (Khan, Ahmad, Arshad et al. et al., 2010; Khan, Ahmad, Sharif et al., 2010).

In the title molecule (I), (Fig. 1), the molecule has a C4—S1—N1—C9 torsion angle of 71.4 (2)°. The dihedral angle between the sulfonyl benzene ring (C1–C6) and the phenyl ring (C10–C15) is 82.83 (16)°. In the structure, molecules are linked into chains along the b axis via C—H···O hydrogen bonding (Table 1, Fig. 2). In the structure, there is a C—H···π interaction (Table 1).

Related literature top

For the pharmacological activities of sulfonamides, see: Maren (1976); Boyd (1988). For our previous studies on derivatives of sulfonamide, see: Khan, Ahmad, Arshad et al. (2010); Khan, Ahmad, Sharif et al. (2010).

Experimental top

A mixture of N-benzyl-4-methylbenzenesulfonamide (0.5 g, 2.02 mmol) and sodium hydride (0.2 g, 8.333 mmol) in N,N-dimethylformamide (10 ml) was stirred at room temperature for 30 min followed by the addition of methyl iodide (0.25 ml, 2.02 mmol). After the consumption of reactants (as monitored by TLC), the contents were poured over crushed ice. The precipitated product was isolated, washed, dried and recrystallized from chloroform solution to yield colourless blocks of title compound.

Structure description top

For the pharmacological activities of sulfonamides, see: Maren (1976); Boyd (1988). For our previous studies on derivatives of sulfonamide, see: Khan, Ahmad, Arshad et al. (2010); Khan, Ahmad, Sharif et al. (2010).

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. The title molecule showing the atomic numbering scheme and 30% probability displacement ellipsoids.
	Fig. 2. The packing and hydrogen bonding of the title compound in the unit cell. Hydrogen bonds are shown as dashed lines. For the sake of clarity, the H atoms not involved in the motif have been omitted.

N-Benzyl-N,4-dimethylbenzenesulfonamide top

Crystal data top

C₁₅H₁₇NO₂S	F(000) = 584
M_r = 275.37	D_x = 1.267 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1987 reflections
a = 15.0386 (16) Å	θ = 2.8–19.5°
b = 8.2632 (7) Å	µ = 0.22 mm⁻¹
c = 12.0758 (12) Å	T = 296 K
β = 105.902 (4)°	Block, colourless
V = 1443.2 (2) Å³	0.28 × 0.17 × 0.09 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	1580 reflections with I > 2σ(I)
Radiation source: sealed tube	R_int = 0.042
Graphite monochromator	θ_max = 28.3°, θ_min = 1.4°
φ and ω scans	h = −19→20
13504 measured reflections	k = −9→11
3569 independent reflections	l = −14→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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.155	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0492P)² + 0.4014P] where P = (F_o² + 2F_c²)/3
3569 reflections	(Δ/σ)_max < 0.001
174 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₅H₁₇NO₂S	V = 1443.2 (2) Å³
M_r = 275.37	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.0386 (16) Å	µ = 0.22 mm⁻¹
b = 8.2632 (7) Å	T = 296 K
c = 12.0758 (12) Å	0.28 × 0.17 × 0.09 mm
β = 105.902 (4)°

Data collection top

Bruker APEXII CCD diffractometer	1580 reflections with I > 2σ(I)
13504 measured reflections	R_int = 0.042
3569 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.155	H-atom parameters constrained
S = 1.01	Δρ_max = 0.18 e Å⁻³
3569 reflections	Δρ_min = −0.24 e Å⁻³
174 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	0.28540 (5)	0.19774 (9)	0.52072 (8)	0.0817 (3)
O1	0.33542 (16)	0.3390 (2)	0.5047 (3)	0.1286 (12)
O2	0.27578 (16)	0.1610 (3)	0.63199 (19)	0.1120 (10)
N1	0.18117 (15)	0.2182 (2)	0.4348 (2)	0.0696 (9)
C1	0.40480 (17)	−0.2407 (4)	0.3876 (2)	0.0683 (10)
C2	0.41527 (19)	−0.0886 (4)	0.3473 (3)	0.0836 (12)
C3	0.38139 (19)	0.0469 (4)	0.3880 (3)	0.0799 (11)
C4	0.33502 (16)	0.0309 (3)	0.4717 (2)	0.0603 (9)
C5	0.32447 (17)	−0.1215 (3)	0.5129 (2)	0.0647 (10)
C6	0.35966 (18)	−0.2545 (3)	0.4714 (2)	0.0685 (10)
C7	0.4415 (2)	−0.3883 (4)	0.3416 (3)	0.1029 (16)
C8	0.1774 (2)	0.2578 (4)	0.3159 (3)	0.1013 (14)
C9	0.11230 (18)	0.0967 (3)	0.4439 (3)	0.0719 (10)
C10	0.01606 (19)	0.1670 (3)	0.4037 (2)	0.0644 (10)
C11	−0.0138 (2)	0.2751 (4)	0.4709 (3)	0.0804 (12)
C12	−0.1020 (3)	0.3421 (4)	0.4332 (4)	0.0991 (16)
C13	−0.1597 (2)	0.2996 (5)	0.3276 (5)	0.1090 (18)
C14	−0.1292 (3)	0.1911 (5)	0.2621 (4)	0.1128 (17)
C15	−0.0424 (2)	0.1256 (4)	0.2990 (3)	0.0876 (12)
H2	0.44620	−0.07680	0.29080	0.1000*
H3	0.38960	0.14860	0.35930	0.0960*
H5	0.29330	−0.13430	0.56900	0.0780*
H6	0.35270	−0.35620	0.50080	0.0820*
H7A	0.47420	−0.45520	0.40460	0.1540*
H7B	0.48270	−0.35560	0.29750	0.1540*
H7C	0.39090	−0.44830	0.29330	0.1540*
H8A	0.19200	0.16320	0.27810	0.1520*
H8B	0.22130	0.34170	0.31490	0.1520*
H8C	0.11630	0.29440	0.27650	0.1520*
H9A	0.12430	0.06140	0.52320	0.0860*
H9B	0.11700	0.00330	0.39720	0.0860*
H11	0.02490	0.30430	0.54230	0.0970*
H12	−0.12190	0.41580	0.47950	0.1190*
H13	−0.21850	0.34440	0.30170	0.1310*
H14	−0.16780	0.16060	0.19100	0.1350*
H15	−0.02290	0.05200	0.25230	0.1050*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0745 (6)	0.0657 (5)	0.1035 (7)	−0.0062 (4)	0.0218 (4)	−0.0202 (4)
O1	0.1010 (18)	0.0631 (13)	0.222 (3)	−0.0296 (12)	0.0449 (18)	−0.0325 (16)
O2	0.1209 (19)	0.139 (2)	0.0748 (15)	0.0202 (15)	0.0246 (13)	−0.0337 (14)
N1	0.0700 (15)	0.0538 (13)	0.0903 (17)	0.0006 (11)	0.0308 (13)	0.0105 (12)
C1	0.0508 (16)	0.081 (2)	0.0685 (18)	0.0036 (13)	0.0088 (14)	−0.0079 (15)
C2	0.072 (2)	0.102 (2)	0.089 (2)	−0.0027 (17)	0.0428 (17)	0.0009 (19)
C3	0.075 (2)	0.0688 (19)	0.105 (2)	−0.0117 (15)	0.0399 (18)	0.0143 (17)
C4	0.0522 (15)	0.0594 (16)	0.0693 (17)	−0.0067 (11)	0.0168 (13)	−0.0028 (13)
C5	0.0607 (16)	0.0711 (18)	0.0654 (17)	−0.0030 (13)	0.0223 (13)	0.0058 (14)
C6	0.0670 (17)	0.0595 (16)	0.0749 (19)	0.0011 (13)	0.0127 (15)	0.0067 (14)
C7	0.088 (2)	0.109 (3)	0.106 (3)	0.0236 (19)	0.017 (2)	−0.027 (2)
C8	0.100 (2)	0.098 (2)	0.115 (3)	0.0158 (18)	0.045 (2)	0.051 (2)
C9	0.0745 (19)	0.0558 (15)	0.089 (2)	−0.0018 (13)	0.0286 (16)	0.0104 (14)
C10	0.0669 (18)	0.0530 (15)	0.0741 (19)	−0.0062 (13)	0.0209 (15)	0.0130 (14)
C11	0.073 (2)	0.081 (2)	0.086 (2)	−0.0004 (16)	0.0199 (17)	0.0049 (18)
C12	0.086 (3)	0.086 (2)	0.138 (3)	0.0105 (19)	0.052 (3)	0.022 (2)
C13	0.063 (2)	0.104 (3)	0.153 (4)	0.003 (2)	0.018 (3)	0.065 (3)
C14	0.089 (3)	0.122 (3)	0.110 (3)	−0.017 (2)	−0.002 (2)	0.031 (3)
C15	0.086 (2)	0.085 (2)	0.087 (2)	−0.0165 (18)	0.0154 (19)	0.0012 (18)

Geometric parameters (Å, º) top

S1—O1	1.430 (2)	C14—C15	1.370 (6)
S1—O2	1.423 (2)	C2—H2	0.9300
S1—N1	1.634 (2)	C3—H3	0.9300
S1—C4	1.746 (3)	C5—H5	0.9300
N1—C8	1.459 (4)	C6—H6	0.9300
N1—C9	1.468 (3)	C7—H7A	0.9600
C1—C2	1.372 (5)	C7—H7B	0.9600
C1—C6	1.369 (4)	C7—H7C	0.9600
C1—C7	1.506 (5)	C8—H8A	0.9600
C2—C3	1.376 (5)	C8—H8B	0.9600
C3—C4	1.383 (4)	C8—H8C	0.9600
C4—C5	1.379 (3)	C9—H9A	0.9700
C5—C6	1.373 (4)	C9—H9B	0.9700
C9—C10	1.511 (4)	C11—H11	0.9300
C10—C11	1.363 (4)	C12—H12	0.9300
C10—C15	1.371 (4)	C13—H13	0.9300
C11—C12	1.394 (6)	C14—H14	0.9300
C12—C13	1.377 (7)	C15—H15	0.9300
C13—C14	1.356 (6)

O1···C6ⁱ	3.414 (3)	H2···H7B^x	2.5000
O1···C7ⁱⁱ	3.384 (4)	H3···O1	2.6500
O2···C8ⁱⁱⁱ	3.061 (4)	H5···O2	2.5900
O1···H6ⁱ	2.5300	H5···C13^ix	2.9700
O1···H8B	2.4600	H6···O1^v	2.5300
O1···H3	2.6500	H6···H7A	2.5500
O2···H5	2.5900	H7A···H6	2.5500
O2···H9A	2.4400	H7A···H7A^xi	2.3400
O2···H7C^iv	2.8300	H7B···H2	2.3600
O2···H8Aⁱⁱⁱ	2.8300	H7B···H2^viii	2.5000
O2···H8Bⁱⁱⁱ	2.5600	H7C···O2^xii	2.8300
C3···C8	3.427 (5)	H8A···C3	2.9500
C5···C9	3.559 (4)	H8A···C4	2.9200
C6···O1^v	3.414 (3)	H8A···H9B	2.4400
C7···O1ⁱⁱ	3.384 (4)	H8A···O2^vi	2.8300
C8···C15	3.434 (5)	H8B···O1	2.4600
C8···C3	3.427 (5)	H8B···O2^vi	2.5600
C8···O2^vi	3.061 (4)	H8C···C10	2.6500
C9···C5	3.559 (4)	H8C···C15	2.8400
C15···C8	3.434 (5)	H8C···C15^xiii	3.0000
C2···H13^vii	3.0600	H8C···H15^xiii	2.5200
C3···H8A	2.9500	H9A···O2	2.4400
C4···H8A	2.9200	H9A···H11	2.5500
C6···H14^vii	3.0900	H9B···H8A	2.4400
C7···H2^viii	3.0500	H9B···H15	2.3700
C10···H8C	2.6500	H11···H9A	2.5500
C13···H5^ix	2.9700	H13···C2^xiii	3.0600
C15···H8C	2.8400	H14···C6^xiii	3.0900
C15···H8C^vii	3.0000	H15···H9B	2.3700
H2···H7B	2.3600	H15···H8C^vii	2.5200
H2···C7^x	3.0500

O1—S1—O2	119.68 (18)	C4—C5—H5	120.00
O1—S1—N1	106.15 (14)	C6—C5—H5	120.00
O1—S1—C4	108.00 (14)	C1—C6—H6	119.00
O2—S1—N1	107.07 (14)	C5—C6—H6	119.00
O2—S1—C4	108.37 (13)	C1—C7—H7A	110.00
N1—S1—C4	106.92 (11)	C1—C7—H7B	110.00
S1—N1—C8	114.8 (2)	C1—C7—H7C	109.00
S1—N1—C9	117.09 (18)	H7A—C7—H7B	109.00
C8—N1—C9	112.9 (2)	H7A—C7—H7C	109.00
C2—C1—C6	117.8 (3)	H7B—C7—H7C	109.00
C2—C1—C7	121.4 (3)	N1—C8—H8A	109.00
C6—C1—C7	120.7 (3)	N1—C8—H8B	109.00
C1—C2—C3	121.9 (3)	N1—C8—H8C	109.00
C2—C3—C4	119.6 (3)	H8A—C8—H8B	110.00
S1—C4—C3	121.4 (2)	H8A—C8—H8C	109.00
S1—C4—C5	119.77 (19)	H8B—C8—H8C	110.00
C3—C4—C5	118.8 (2)	N1—C9—H9A	110.00
C4—C5—C6	120.4 (2)	N1—C9—H9B	110.00
C1—C6—C5	121.5 (2)	C10—C9—H9A	110.00
N1—C9—C10	110.3 (2)	C10—C9—H9B	110.00
C9—C10—C11	120.2 (3)	H9A—C9—H9B	108.00
C9—C10—C15	121.1 (3)	C10—C11—H11	120.00
C11—C10—C15	118.7 (3)	C12—C11—H11	120.00
C10—C11—C12	120.3 (3)	C11—C12—H12	120.00
C11—C12—C13	120.2 (4)	C13—C12—H12	120.00
C12—C13—C14	118.7 (4)	C12—C13—H13	121.00
C13—C14—C15	121.1 (4)	C14—C13—H13	121.00
C10—C15—C14	121.0 (3)	C13—C14—H14	120.00
C1—C2—H2	119.00	C15—C14—H14	119.00
C3—C2—H2	119.00	C10—C15—H15	120.00
C2—C3—H3	120.00	C14—C15—H15	119.00
C4—C3—H3	120.00

O1—S1—N1—C8	50.6 (2)	C7—C1—C2—C3	179.5 (3)
O2—S1—N1—C8	179.5 (2)	C1—C2—C3—C4	−0.2 (5)
C4—S1—N1—C8	−64.5 (2)	C2—C3—C4—C5	0.4 (4)
O1—S1—N1—C9	−173.5 (2)	C2—C3—C4—S1	−176.6 (2)
O2—S1—N1—C9	−44.5 (2)	S1—C4—C5—C6	177.2 (2)
C4—S1—N1—C9	71.4 (2)	C3—C4—C5—C6	0.1 (4)
O1—S1—C4—C3	−26.5 (3)	C4—C5—C6—C1	−0.9 (4)
O2—S1—C4—C3	−157.5 (2)	N1—C9—C10—C11	−74.0 (3)
N1—S1—C4—C3	87.4 (2)	N1—C9—C10—C15	105.2 (3)
O1—S1—C4—C5	156.6 (2)	C9—C10—C11—C12	179.0 (3)
O2—S1—C4—C5	25.5 (2)	C15—C10—C11—C12	−0.2 (5)
N1—S1—C4—C5	−89.6 (2)	C9—C10—C15—C14	−179.2 (3)
C8—N1—C9—C10	−68.8 (3)	C11—C10—C15—C14	0.0 (5)
S1—N1—C9—C10	154.48 (19)	C10—C11—C12—C13	0.0 (6)
C6—C1—C2—C3	−0.5 (4)	C11—C12—C13—C14	0.5 (6)
C7—C1—C6—C5	−178.9 (3)	C12—C13—C14—C15	−0.7 (6)
C2—C1—C6—C5	1.1 (4)	C13—C14—C15—C10	0.4 (6)

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

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C10–C15 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O2	0.93	2.59	2.938 (3)	103
C6—H6···O1^v	0.93	2.53	3.414 (3)	158
C8—H8B···O1	0.96	2.46	2.886 (5)	107
C8—H8B···O2^vi	0.96	2.56	3.061 (4)	113
C9—H9A···O2	0.97	2.44	2.903 (4)	109
C9—H9A···Cg2^ix	0.97	2.99	3.721 (3)	133

Symmetry codes: (v) x, y−1, z; (vi) x, −y+1/2, z−1/2; (ix) −x, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₇NO₂S
M_r	275.37
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	15.0386 (16), 8.2632 (7), 12.0758 (12)
β (°)	105.902 (4)
V (Å³)	1443.2 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.28 × 0.17 × 0.09

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	13504, 3569, 1580
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.155, 1.01
No. of reflections	3569
No. of parameters	174
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.24

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

Cg2 is the centroid of the C10–C15 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1ⁱ	0.93	2.53	3.414 (3)	158
C9—H9A···Cg2ⁱⁱ	0.97	2.99	3.721 (3)	133

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

Acknowledgements

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

References

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Volume 66| Part 12| December 2010| Page o3053

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