N-(3-Eth­oxy­phen­yl)-4-methyl­benzene­sulfonamide

Aziz-ur-Rehman; Siddiqa, A.; Akkurt, M.; Abbasi, M.A.; Jahangir, M.; Khan, I.U.

doi:10.1107/S1600536810022427

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1682

doi:10.1107/S1600536810022427

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N-(3-Ethoxyphenyl)-4-methylbenzenesulfonamide

Aziz-ur-Rehman,^a ‡ Asia Siddiqa,^a Mehmet Akkurt,^b ^* Muhammad Athar Abbasi,^a Muhammad Jahangir ^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 9 June 2010; accepted 11 June 2010; online 16 June 2010)

In the title compound, C₁₅H₁₇NO₃S, the two aromatic rings make a dihedral angle of 69.42 (9)° with each other and the bridging C—N—S—C torsion angle is 65.76 (16)°. Weak intramolecular C—H⋯O interactions may affect the molecular conformation. Two neighbouring molecules generate a hydrogen-bonded dimer about a center of inversion through a pair of intermolecular N—H⋯O interactions, forming an R₂²(8) ring motif. Furthermore, two intermolecular C—H⋯π interactions contribute to the stability of the crystal packing.

Related literature

For the biological activity of sulfonamides, see: Berredjem et al. (2000 ); Lee & Lee (2002 ); Soledade et al. (2006 ); Xiao & Timberlake (2000 ).

Experimental

Crystal data

C₁₅H₁₇NO₃S
M_r = 291.37
Monoclinic, P 2₁ /c
a = 8.4612 (3) Å
b = 13.1862 (5) Å
c = 13.4237 (4) Å
β = 99.326 (2)°
V = 1477.90 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 296 K
0.34 × 0.18 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer
13221 measured reflections
3608 independent reflections
2532 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.118
S = 1.00
3608 reflections
186 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C2–C7 and C8–C13 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2ⁱ	0.821 (16)	2.140 (17)	2.9476 (19)	167.9 (16)
C4—H4⋯O2	0.93	2.54	2.914 (2)	104
C13—H13⋯O1	0.93	2.42	3.019 (2)	122
C14—H14A⋯Cg1ⁱⁱ	0.97	2.90	3.752 (3)	147
C15—H15C⋯Cg2ⁱⁱⁱ	0.96	2.96	3.763 (3)	147
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) -x+1, -y+1, -z.

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/S1600536810022427/sj5019sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810022427/sj5019Isup2.hkl

checkCIF report

Comment top

Sulfonamide is an important functionality found in a number of synthetic as well as natural compounds possessing versatile type of biological activities e.g. herbicidal, anti-malarial, anti-convulsant and anti-hypertensive (Soledade et al., 2006; Xiao & Timberlake, 2000; Berredjem et al., 2000; Lee & Lee, 2002) activities. In the present paper, the structure of N-(3-ethoxyphenyl)-4-methylbenzene sulfonamide has been determined as part of a research program involving the synthesis and biological evaluation of sulfur containing compounds.

In the title compound (I), Fig. 1), the dihedral angle between the two aromatic rings (C2–C7 and C8–C13) is 69.42 (9)° and the bridging C5—S1—N1—C8 torsion angle is 65.76 (16)°. In the crystal structure, two neighbouring molecules generate a hydrogen-bonded dimer about a center of inversion through a pair of intermolecular N—H···O interactions, forming an R₂²(8) ring motif (Table 1, Fig. 2).

In the structure, two intermolecular C—H···π interactions contribute to the stability of crystal packing (Table 1).

Related literature top

For the biological activity of sulfonamides, see: Berredjem et al. (2000); Lee & Lee (2002); Soledade et al. (2006); Xiao & Timberlake (2000).

Experimental top

A mixture of 4-methyl benzene sulfonyl chloride (10.0 mmoles; 1.90 g), 3-ethoxy aniline (meta-phenetidine) (10.0 mmoles; 1.25 g), aqueous sodium carbonate (10%; 10.0 ml) and water (25 ml) was stirred for half an hour at room temperature. The crude mixture was washed with water and dried. Product was dissolved in methanol and crystallized by slow evaporation of the solvent. Yield 72%. 4-Methyl benzene sulfonyl chloride and meta-phenetidine were purchased from Sigma Aldrich while all other chemicals involved were obtained from Merk, Germany.

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 of (I), with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. View of the N—H···O dimer in the unit cell of (I). H-atoms not involved in hydrogen bonds have been omitted for clarity.

N-(3-Ethoxyphenyl)-4-methylbenzenesulfonamide top

Crystal data top

C₁₅H₁₇NO₃S	F(000) = 616
M_r = 291.37	D_x = 1.309 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4223 reflections
a = 8.4612 (3) Å	θ = 2.9–26.1°
b = 13.1862 (5) Å	µ = 0.23 mm⁻¹
c = 13.4237 (4) Å	T = 296 K
β = 99.326 (2)°	Needle, colourless
V = 1477.90 (9) Å³	0.34 × 0.18 × 0.16 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	2532 reflections with I > 2σ(I)
Radiation source: sealed tube	R_int = 0.036
Graphite monochromator	θ_max = 28.3°, θ_min = 3.4°
ϕ and ω scans	h = −11→11
13221 measured reflections	k = −17→15
3608 independent reflections	l = −17→17

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0564P)² + 0.2791P] where P = (F_o² + 2F_c²)/3
3608 reflections	(Δ/σ)_max < 0.001
186 parameters	Δρ_max = 0.30 e Å⁻³
1 restraint	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₁₅H₁₇NO₃S	V = 1477.90 (9) Å³
M_r = 291.37	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.4612 (3) Å	µ = 0.23 mm⁻¹
b = 13.1862 (5) Å	T = 296 K
c = 13.4237 (4) Å	0.34 × 0.18 × 0.16 mm
β = 99.326 (2)°

Data collection top

Bruker APEXII CCD diffractometer	2532 reflections with I > 2σ(I)
13221 measured reflections	R_int = 0.036
3608 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	1 restraint
wR(F²) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.30 e Å⁻³
3608 reflections	Δρ_min = −0.31 e Å⁻³
186 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	0.26616 (5)	0.52544 (3)	0.38686 (3)	0.0408 (1)
O1	0.17864 (15)	0.57574 (10)	0.30139 (9)	0.0518 (4)
O2	0.32376 (14)	0.58201 (9)	0.47639 (9)	0.0495 (4)
O3	0.30011 (17)	0.42300 (12)	−0.00035 (9)	0.0653 (5)
N1	0.42808 (16)	0.47848 (12)	0.35383 (11)	0.0439 (5)
C1	−0.1104 (3)	0.1674 (2)	0.4986 (2)	0.1033 (13)
C2	−0.0197 (2)	0.25798 (16)	0.47044 (18)	0.0623 (7)
C3	0.0767 (2)	0.31285 (17)	0.54323 (16)	0.0639 (8)
C4	0.1627 (2)	0.39529 (15)	0.51876 (14)	0.0532 (6)
C5	0.15151 (18)	0.42365 (13)	0.41926 (13)	0.0414 (5)
C6	0.0547 (2)	0.37042 (16)	0.34460 (15)	0.0562 (7)
C7	−0.0295 (2)	0.28784 (18)	0.37117 (18)	0.0673 (8)
C8	0.43243 (18)	0.41644 (13)	0.26721 (12)	0.0402 (5)
C9	0.5253 (2)	0.32988 (15)	0.28030 (15)	0.0548 (6)
C10	0.5428 (3)	0.27331 (17)	0.19682 (16)	0.0668 (8)
C11	0.4705 (2)	0.30085 (16)	0.10134 (15)	0.0591 (7)
C12	0.3773 (2)	0.38714 (15)	0.08949 (13)	0.0484 (6)
C13	0.3581 (2)	0.44493 (14)	0.17269 (13)	0.0466 (5)
C14	0.3347 (3)	0.37772 (18)	−0.09048 (13)	0.0624 (7)
C15	0.2431 (3)	0.4353 (2)	−0.17758 (16)	0.0836 (9)
H1A	−0.20100	0.15520	0.44690	0.1550*
H1B	−0.14680	0.18010	0.56160	0.1550*
H1C	−0.04160	0.10910	0.50520	0.1550*
H1N	0.486 (2)	0.4612 (14)	0.4062 (12)	0.0530*
H3	0.08400	0.29390	0.61060	0.0770*
H4	0.22780	0.43140	0.56900	0.0640*
H6	0.04630	0.38990	0.27740	0.0670*
H7	−0.09440	0.25150	0.32100	0.0810*
H9	0.57500	0.31030	0.34430	0.0660*
H10	0.60510	0.21490	0.20500	0.0800*
H11	0.48420	0.26180	0.04570	0.0710*
H13	0.29490	0.50300	0.16470	0.0560*
H14A	0.30240	0.30710	−0.09370	0.0750*
H14B	0.44870	0.38110	−0.09240	0.0750*
H15A	0.13040	0.42930	−0.17630	0.1250*
H15B	0.26700	0.40800	−0.23980	0.1250*
H15C	0.27350	0.50550	−0.17240	0.1250*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0391 (2)	0.0417 (2)	0.0397 (2)	0.0033 (2)	0.0004 (2)	−0.0018 (2)
O1	0.0518 (7)	0.0531 (8)	0.0479 (7)	0.0098 (6)	0.0001 (6)	0.0050 (6)
O2	0.0518 (7)	0.0455 (7)	0.0489 (7)	0.0015 (6)	0.0017 (5)	−0.0086 (5)
O3	0.0699 (9)	0.0826 (11)	0.0410 (7)	0.0166 (8)	0.0018 (6)	−0.0055 (7)
N1	0.0358 (7)	0.0540 (9)	0.0399 (8)	0.0022 (7)	0.0003 (6)	−0.0013 (7)
C1	0.0842 (17)	0.085 (2)	0.149 (3)	−0.0305 (15)	0.0439 (18)	−0.0015 (18)
C2	0.0435 (10)	0.0584 (13)	0.0886 (15)	−0.0062 (9)	0.0214 (10)	−0.0050 (11)
C3	0.0656 (12)	0.0657 (14)	0.0642 (13)	−0.0056 (11)	0.0218 (10)	0.0055 (10)
C4	0.0529 (10)	0.0608 (12)	0.0452 (10)	−0.0080 (9)	0.0060 (8)	−0.0050 (8)
C5	0.0345 (8)	0.0430 (10)	0.0457 (9)	0.0040 (7)	0.0037 (7)	−0.0041 (7)
C6	0.0475 (10)	0.0644 (13)	0.0532 (11)	−0.0058 (9)	−0.0022 (8)	−0.0056 (9)
C7	0.0462 (11)	0.0712 (15)	0.0816 (15)	−0.0128 (10)	0.0013 (10)	−0.0184 (12)
C8	0.0346 (8)	0.0438 (10)	0.0425 (9)	−0.0024 (7)	0.0069 (7)	0.0006 (7)
C9	0.0572 (11)	0.0536 (12)	0.0514 (10)	0.0122 (9)	0.0018 (9)	0.0024 (9)
C10	0.0728 (13)	0.0579 (13)	0.0669 (13)	0.0228 (11)	0.0030 (11)	−0.0065 (10)
C11	0.0590 (11)	0.0627 (13)	0.0549 (11)	0.0076 (10)	0.0076 (9)	−0.0155 (9)
C12	0.0431 (9)	0.0583 (11)	0.0428 (9)	0.0007 (8)	0.0044 (7)	−0.0032 (8)
C13	0.0441 (9)	0.0489 (10)	0.0459 (9)	0.0067 (8)	0.0049 (7)	0.0001 (8)
C14	0.0626 (12)	0.0828 (15)	0.0420 (10)	−0.0107 (11)	0.0092 (9)	−0.0129 (10)
C15	0.0858 (16)	0.116 (2)	0.0468 (12)	−0.0155 (16)	0.0038 (11)	0.0010 (13)

Geometric parameters (Å, º) top

S1—O1	1.4245 (13)	C11—C12	1.379 (3)
S1—O2	1.4313 (13)	C12—C13	1.383 (3)
S1—N1	1.6291 (15)	C14—C15	1.500 (3)
S1—C5	1.7517 (17)	C1—H1A	0.9600
O3—C12	1.360 (2)	C1—H1B	0.9600
O3—C14	1.422 (2)	C1—H1C	0.9600
N1—C8	1.427 (2)	C3—H3	0.9300
N1—H1N	0.821 (16)	C4—H4	0.9300
C1—C2	1.501 (3)	C6—H6	0.9300
C2—C7	1.379 (3)	C7—H7	0.9300
C2—C3	1.373 (3)	C9—H9	0.9300
C3—C4	1.377 (3)	C10—H10	0.9300
C4—C5	1.375 (3)	C11—H11	0.9300
C5—C6	1.379 (3)	C13—H13	0.9300
C6—C7	1.379 (3)	C14—H14A	0.9700
C8—C13	1.374 (2)	C14—H14B	0.9700
C8—C9	1.381 (3)	C15—H15A	0.9600
C9—C10	1.374 (3)	C15—H15B	0.9600
C10—C11	1.377 (3)	C15—H15C	0.9600

S1···H13	3.0500	H1N···O2ⁱⁱ	2.140 (17)
S1···H10ⁱ	3.0600	H3···H1B	2.4700
O1···C13	3.019 (2)	H4···O2	2.5400
O2···N1ⁱⁱ	2.9476 (19)	H4···H15B^vii	2.5500
O1···H13	2.4200	H6···O1	2.6900
O1···H7ⁱⁱⁱ	2.8600	H7···H1A	2.4000
O1···H10ⁱ	2.6000	H7···O1^vi	2.8600
O1···H15A^iv	2.8700	H9···H1N	2.3300
O1···H6	2.6900	H9···O2ⁱⁱ	2.8100
O2···H4	2.5400	H10···S1^viii	3.0600
O2···H11ⁱ	2.9200	H10···O1^viii	2.6000
O2···H1Nⁱⁱ	2.140 (17)	H11···C14	2.5600
O2···H9ⁱⁱ	2.8100	H11···H14A	2.3000
N1···O2ⁱⁱ	2.9476 (19)	H11···H14B	2.4100
C6···C8	3.569 (2)	H11···O2^viii	2.9200
C8···C6	3.569 (2)	H13···S1	3.0500
C13···O1	3.019 (2)	H13···O1	2.4200
C7···H14A^v	3.0400	H13···H1Aⁱⁱⁱ	2.5500
C11···H14A	2.7700	H14A···C11	2.7700
C11···H14B	2.7900	H14A···H11	2.3000
C14···H11	2.5600	H14A···C7^ix	3.0400
H1A···H7	2.4000	H14B···C11	2.7900
H1A···H13^vi	2.5500	H14B···H11	2.4100
H1B···H3	2.4700	H15A···O1^iv	2.8700
H1N···H9	2.3300	H15B···H4^x	2.5500

O1—S1—O2	119.70 (8)	C2—C1—H1B	109.00
O1—S1—N1	107.95 (8)	C2—C1—H1C	109.00
O1—S1—C5	108.68 (8)	H1A—C1—H1B	109.00
O2—S1—N1	103.87 (7)	H1A—C1—H1C	109.00
O2—S1—C5	108.53 (8)	H1B—C1—H1C	110.00
N1—S1—C5	107.48 (8)	C2—C3—H3	119.00
C12—O3—C14	118.24 (16)	C4—C3—H3	119.00
S1—N1—C8	125.00 (11)	C3—C4—H4	120.00
C8—N1—H1N	116.6 (12)	C5—C4—H4	120.00
S1—N1—H1N	106.5 (12)	C5—C6—H6	121.00
C1—C2—C7	121.2 (2)	C7—C6—H6	121.00
C3—C2—C7	118.23 (19)	C2—C7—H7	119.00
C1—C2—C3	120.6 (2)	C6—C7—H7	119.00
C2—C3—C4	121.5 (2)	C8—C9—H9	121.00
C3—C4—C5	119.36 (17)	C10—C9—H9	121.00
S1—C5—C4	119.72 (13)	C9—C10—H10	119.00
C4—C5—C6	120.44 (17)	C11—C10—H10	119.00
S1—C5—C6	119.81 (14)	C10—C11—H11	120.00
C5—C6—C7	118.99 (19)	C12—C11—H11	121.00
C2—C7—C6	121.5 (2)	C8—C13—H13	120.00
N1—C8—C9	117.35 (15)	C12—C13—H13	120.00
N1—C8—C13	121.82 (15)	O3—C14—H14A	110.00
C9—C8—C13	120.63 (16)	O3—C14—H14B	110.00
C8—C9—C10	118.64 (18)	C15—C14—H14A	110.00
C9—C10—C11	121.7 (2)	C15—C14—H14B	110.00
C10—C11—C12	118.99 (19)	H14A—C14—H14B	108.00
O3—C12—C13	114.97 (17)	C14—C15—H15A	109.00
O3—C12—C11	124.94 (17)	C14—C15—H15B	109.00
C11—C12—C13	120.09 (17)	C14—C15—H15C	109.00
C8—C13—C12	119.93 (17)	H15A—C15—H15B	110.00
O3—C14—C15	107.41 (19)	H15A—C15—H15C	109.00
C2—C1—H1A	109.00	H15B—C15—H15C	109.00

O1—S1—N1—C8	−51.29 (16)	C1—C2—C3—C4	179.04 (19)
O2—S1—N1—C8	−179.35 (14)	C2—C3—C4—C5	0.2 (3)
C5—S1—N1—C8	65.76 (16)	C3—C4—C5—C6	0.3 (3)
O1—S1—C5—C4	−147.64 (14)	C3—C4—C5—S1	−177.61 (14)
O2—S1—C5—C4	−15.96 (16)	C4—C5—C6—C7	−0.6 (3)
N1—S1—C5—C4	95.79 (15)	S1—C5—C6—C7	177.28 (14)
O1—S1—C5—C6	34.49 (16)	C5—C6—C7—C2	0.4 (3)
O2—S1—C5—C6	166.16 (14)	N1—C8—C9—C10	−174.51 (18)
N1—S1—C5—C6	−82.09 (15)	C9—C8—C13—C12	−0.6 (3)
C14—O3—C12—C13	169.88 (18)	N1—C8—C13—C12	174.16 (16)
C12—O3—C14—C15	−176.27 (18)	C13—C8—C9—C10	0.5 (3)
C14—O3—C12—C11	−9.5 (3)	C8—C9—C10—C11	0.0 (3)
S1—N1—C8—C9	−133.67 (15)	C9—C10—C11—C12	−0.4 (3)
S1—N1—C8—C13	51.4 (2)	C10—C11—C12—C13	0.3 (3)
C3—C2—C7—C6	0.1 (3)	C10—C11—C12—O3	179.66 (19)
C1—C2—C7—C6	−179.4 (2)	O3—C12—C13—C8	−179.21 (16)
C7—C2—C3—C4	−0.4 (3)	C11—C12—C13—C8	0.2 (3)

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

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C2–C7 and C8–C13 benzene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ⁱⁱ	0.821 (16)	2.140 (17)	2.9476 (19)	167.9 (16)
C4—H4···O2	0.93	2.54	2.914 (2)	104
C13—H13···O1	0.93	2.42	3.019 (2)	122
C14—H14A···Cg1^ix	0.97	2.90	3.752 (3)	147
C15—H15C···Cg2^xi	0.96	2.96	3.763 (3)	147

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

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)	8.4612 (3), 13.1862 (5), 13.4237 (4)
β (°)	99.326 (2)
V (Å³)	1477.90 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.34 × 0.18 × 0.16

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	13221, 3608, 2532
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.118, 1.00
No. of reflections	3608
No. of parameters	186
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.31

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

Cg1 and Cg2 are the centroids of the C2–C7 and C8–C13 benzene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ⁱ	0.821 (16)	2.140 (17)	2.9476 (19)	167.9 (16)
C4—H4···O2	0.93	2.54	2.914 (2)	104
C13—H13···O1	0.93	2.42	3.019 (2)	122
C14—H14A···Cg1ⁱⁱ	0.97	2.90	3.752 (3)	147
C15—H15C···Cg2ⁱⁱⁱ	0.96	2.96	3.763 (3)	147

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

Footnotes

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

Acknowledgements

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

References

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Volume 66| Part 7| July 2010| Page o1682

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