N-{[4-(4-Meth­oxy­benzene­sulfonamido)­phen­yl]sulfon­yl}acetamide

Mustafa, G.; Akkurt, M.; Khan, I.U.; Naseem, R.; Sajjad, B.

doi:10.1107/S1600536810023925

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1768

doi:10.1107/S1600536810023925

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N-{[4-(4-Methoxybenzenesulfonamido)phenyl]sulfonyl}acetamide

Ghulam Mustafa,^a Mehmet Akkurt,^b ^* Islam Ullah Khan,^c Rahat Naseem ^a and Beenish Sajjad ^a

^aDepartment of Chemistry, University of Gujrat, H. H. Campus, Gujrat 50700, Pakistan, ^bDepartment of Physics, Faculty of Arts and Sciences, Erciyes University, 38039 Kayseri, Turkey, and ^cMaterials Chemistry Laboratory, Department of Chemistry, Government College University, Lahore 54000, Pakistan
^*Correspondence e-mail: akkurt@erciyes.edu.tr, iukhan.gcu@gmail.com

(Received 16 June 2010; accepted 20 June 2010; online 23 June 2010)

In the title compound, C₁₅H₁₆N₂O₆S₂, the dihedral angle between the benzene rings is 83.2 (3)°. The molecular conformation is stabilized by an intramolecular C—H⋯O interaction. In the crystal structure, molecules are linked by N—H⋯O and C—H⋯O hydrogen bonds and additional stabilization is provided by weak C—H⋯π interactions.

Related literature

For previous studies on the synthesis of sulfonamide derivatives with phenyl glycine, see: Ashfaq et al. (2009 , 2010 ).

Experimental

Crystal data

C₁₅H₁₆N₂O₆S₂
M_r = 384.44
Monoclinic, P 2₁ /c
a = 5.3651 (10) Å
b = 20.551 (3) Å
c = 15.034 (2) Å
β = 94.040 (7)°
V = 1653.5 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.36 mm⁻¹
T = 296 K
0.25 × 0.08 × 0.07 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
13678 measured reflections
3771 independent reflections
1608 reflections with I > 2σ(I)
R_int = 0.114

Refinement

R[F² > 2σ(F²)] = 0.084
wR(F²) = 0.189
S = 0.89
3771 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.83 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O4ⁱ	0.86	2.09	2.932 (5)	168
N2—H2⋯O5ⁱⁱ	0.86	2.26	3.071 (5)	157
C13—H13⋯O2	0.93	2.35	2.986 (6)	126
C15—H15C⋯O6ⁱⁱ	0.96	2.45	3.348 (7)	156
C15—H15B⋯Cg1ⁱⁱⁱ	0.96	2.79	3.722 (6)	164
C15—H15A⋯Cg2ⁱⁱⁱ	0.96	2.79	3.589 (6)	141
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) x+1, y, z; (iii) -x+2, -y, -z+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 (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/S1600536810023925/hb5502sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810023925/hb5502Isup2.hkl

checkCIF report

Comment top

Sulphacetamide sodium is an antibiotic which is being used for eye infections. Because the antiobiotics lose their efficacy after long term used, so there is a need to derivatize them to get better therapeutic result. In this paper, a new derivative of it is being reported. Previously this drug has also been derivatized by other researchers (Ashfaq et al., 2009, 2010). Here we present the crystal structure of the title compound (I), (Fig. 1).

In (I), the benzene rings (C1–C6) and (C8–C13) are twisted with a dihedral angle of 83.2 (3) ° to each other. Molecular conformation is stabilized by intramolecular C–H···O interactions. Intermolecular N—H···O and C—H···O hydrogen bonds and C—H···π interactions contribute to the stabilization of the crystal structure (Table 1, Fig. 2).

Related literature top

For previous studies on the synthesis of sulfonamide derivatives with phenyl glycine, see: Ashfaq et al. (2009, 2010).

Experimental top

Sodium sulphacetamide (0.5 g, 2.32 mmol) was taken in 50 ml round bottom flask and dissolved in 20 ml of distilled water. Then, methoxy benzene sulfonyl chloride (0.46 g, 2.32 mmol) was added with continuous stirring at ambient temperature. The pH of this solution was strictly maintained between 8 and 9 by using NaHCO₃ (3 M). The consumption of suspended methoxy benzene sulfonyl chloride was an indication of reaction completion. Then pH was adjusted to 2–3 using HCl (3 N). The precipitates formed were filtered, washed three to four times with distilled water and recrystallised using methanol to yield colourless rods of (I).

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

Figures top

	Fig. 1. The title molecule with displacement ellipsoids for non-H atoms drawn at the 30% probability level.
	Fig. 2. The packing and hydrogen bonding of (I) viewed down a axis. H atoms not participating in hydrogen bonding have been omitted for clarity.

N-{[4-(4-Methoxybenzenesulfonamido)phenyl]sulfonyl}acetamide top

Crystal data top

C₁₅H₁₆N₂O₆S₂	F(000) = 800
M_r = 384.44	D_x = 1.544 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1463 reflections
a = 5.3651 (10) Å	θ = 2.9–20.1°
b = 20.551 (3) Å	µ = 0.36 mm⁻¹
c = 15.034 (2) Å	T = 296 K
β = 94.040 (7)°	Rod, colourless
V = 1653.5 (4) Å³	0.25 × 0.08 × 0.07 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	1608 reflections with I > 2σ(I)
Radiation source: sealed tube	R_int = 0.114
Graphite monochromator	θ_max = 28.4°, θ_min = 3.3°
phi and ω scans	h = −7→7
13678 measured reflections	k = −27→26
3771 independent reflections	l = −20→20

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)] = 0.084	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.189	H-atom parameters constrained
S = 0.89	w = 1/[σ²(F_o²) + (0.068P)²] where P = (F_o² + 2F_c²)/3
3771 reflections	(Δ/σ)_max < 0.001
226 parameters	Δρ_max = 0.83 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₁₅H₁₆N₂O₆S₂	V = 1653.5 (4) Å³
M_r = 384.44	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.3651 (10) Å	µ = 0.36 mm⁻¹
b = 20.551 (3) Å	T = 296 K
c = 15.034 (2) Å	0.25 × 0.08 × 0.07 mm
β = 94.040 (7)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	1608 reflections with I > 2σ(I)
13678 measured reflections	R_int = 0.114
3771 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.084	0 restraints
wR(F²) = 0.189	H-atom parameters constrained
S = 0.89	Δρ_max = 0.83 e Å⁻³
3771 reflections	Δρ_min = −0.32 e Å⁻³
226 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	0.3465 (3)	0.17871 (7)	0.68802 (9)	0.0373 (5)
S2	0.7590 (2)	0.14262 (6)	1.14309 (8)	0.0290 (4)
O1	0.7672 (11)	−0.0692 (3)	0.5765 (3)	0.082 (2)
O2	0.1176 (7)	0.16711 (19)	0.7264 (2)	0.0455 (14)
O3	0.3551 (7)	0.2208 (2)	0.6128 (2)	0.0515 (16)
O4	0.8828 (6)	0.19627 (17)	1.1877 (2)	0.0386 (11)
O5	0.5388 (6)	0.11632 (18)	1.1764 (2)	0.0377 (11)
O6	0.7458 (7)	0.00642 (18)	1.0809 (3)	0.0444 (14)
N1	0.5446 (8)	0.2099 (2)	0.7634 (2)	0.0348 (14)
N2	0.9779 (7)	0.0863 (2)	1.1487 (3)	0.0335 (14)
C1	0.4677 (10)	0.1033 (3)	0.6585 (3)	0.0373 (19)
C2	0.6748 (11)	0.1020 (3)	0.6078 (4)	0.051 (2)
C3	0.7658 (13)	0.0438 (4)	0.5824 (4)	0.060 (3)
C4	0.6569 (12)	−0.0140 (4)	0.6055 (4)	0.055 (2)
C5	0.4498 (13)	−0.0129 (3)	0.6561 (4)	0.054 (2)
C6	0.3601 (11)	0.0463 (3)	0.6810 (4)	0.0450 (19)
C7	0.671 (2)	−0.1301 (4)	0.5999 (5)	0.102 (4)
C8	0.5896 (9)	0.1915 (2)	0.8531 (3)	0.0274 (16)
C9	0.7968 (9)	0.2181 (3)	0.8989 (3)	0.0345 (17)
C10	0.8521 (9)	0.2034 (3)	0.9879 (3)	0.0353 (17)
C11	0.6938 (9)	0.1611 (2)	1.0304 (3)	0.0278 (16)
C12	0.4918 (9)	0.1342 (2)	0.9844 (3)	0.0322 (17)
C13	0.4361 (10)	0.1492 (3)	0.8956 (3)	0.0345 (17)
C14	0.9434 (9)	0.0225 (3)	1.1177 (3)	0.0310 (17)
C15	1.1613 (10)	−0.0206 (3)	1.1364 (4)	0.0426 (17)
H1	0.63300	0.24180	0.74610	0.0420*
H2	1.12300	0.09690	1.17230	0.0400*
H2A	0.75010	0.14060	0.59160	0.0610*
H3	0.90470	0.04290	0.54880	0.0720*
H5	0.37410	−0.05130	0.67260	0.0650*
H6	0.22080	0.04750	0.71450	0.0540*
H7A	0.66710	−0.13270	0.66350	0.1520*
H7B	0.77580	−0.16400	0.57940	0.1520*
H7C	0.50490	−0.13500	0.57270	0.1520*
H9	0.90000	0.24620	0.86980	0.0420*
H10	0.99190	0.22120	1.01900	0.0420*
H12	0.39030	0.10540	1.01310	0.0380*
H13	0.29670	0.13110	0.86470	0.0420*
H15A	1.12360	−0.06320	1.11290	0.0640*
H15B	1.19890	−0.02350	1.19970	0.0640*
H15C	1.30280	−0.00320	1.10880	0.0640*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0361 (8)	0.0443 (9)	0.0310 (7)	0.0051 (6)	−0.0015 (6)	0.0047 (6)
S2	0.0303 (7)	0.0313 (7)	0.0256 (6)	0.0004 (5)	0.0039 (5)	−0.0046 (5)
O1	0.110 (4)	0.070 (4)	0.066 (3)	0.033 (3)	0.003 (3)	−0.024 (3)
O2	0.032 (2)	0.054 (3)	0.050 (2)	0.0047 (18)	−0.0006 (17)	−0.0042 (19)
O3	0.061 (3)	0.058 (3)	0.034 (2)	0.008 (2)	−0.0071 (19)	0.0161 (19)
O4	0.045 (2)	0.034 (2)	0.0362 (19)	−0.0048 (17)	−0.0013 (17)	−0.0108 (17)
O5	0.0298 (19)	0.050 (2)	0.0343 (19)	0.0003 (17)	0.0090 (15)	−0.0001 (17)
O6	0.034 (2)	0.035 (2)	0.063 (3)	−0.0026 (17)	−0.0055 (18)	−0.0050 (19)
N1	0.040 (2)	0.036 (3)	0.028 (2)	−0.006 (2)	−0.0013 (19)	0.0099 (19)
N2	0.027 (2)	0.038 (3)	0.034 (2)	−0.0021 (19)	−0.0081 (18)	0.001 (2)
C1	0.033 (3)	0.048 (4)	0.030 (3)	−0.001 (3)	−0.005 (2)	−0.002 (2)
C2	0.046 (4)	0.056 (4)	0.050 (4)	−0.010 (3)	0.003 (3)	−0.011 (3)
C3	0.050 (4)	0.083 (5)	0.048 (4)	0.006 (4)	0.010 (3)	−0.018 (4)
C4	0.054 (4)	0.067 (5)	0.042 (3)	0.019 (4)	−0.014 (3)	−0.015 (3)
C5	0.072 (5)	0.045 (4)	0.043 (3)	0.007 (3)	−0.010 (3)	0.002 (3)
C6	0.048 (3)	0.052 (4)	0.035 (3)	0.003 (3)	0.004 (3)	0.003 (3)
C7	0.189 (10)	0.054 (5)	0.060 (5)	0.039 (6)	−0.002 (6)	−0.005 (4)
C8	0.029 (3)	0.025 (3)	0.028 (2)	0.004 (2)	0.001 (2)	0.005 (2)
C9	0.036 (3)	0.033 (3)	0.035 (3)	−0.014 (2)	0.007 (2)	0.005 (2)
C10	0.033 (3)	0.036 (3)	0.037 (3)	−0.004 (2)	0.003 (2)	−0.004 (2)
C11	0.033 (3)	0.026 (3)	0.025 (2)	0.002 (2)	0.006 (2)	−0.002 (2)
C12	0.034 (3)	0.029 (3)	0.033 (3)	−0.009 (2)	−0.001 (2)	0.003 (2)
C13	0.031 (3)	0.039 (3)	0.033 (3)	−0.004 (2)	−0.002 (2)	0.004 (2)
C14	0.026 (3)	0.037 (3)	0.030 (3)	−0.004 (2)	0.002 (2)	0.003 (2)
C15	0.037 (3)	0.041 (3)	0.050 (3)	0.013 (3)	0.004 (2)	−0.002 (3)

Geometric parameters (Å, º) top

S1—O2	1.413 (4)	C8—C13	1.384 (7)
S1—O3	1.427 (4)	C8—C9	1.379 (7)
S1—N1	1.629 (4)	C9—C10	1.383 (7)
S1—C1	1.750 (6)	C10—C11	1.401 (7)
S2—O4	1.430 (4)	C11—C12	1.361 (7)
S2—O5	1.422 (3)	C12—C13	1.382 (6)
S2—N2	1.647 (4)	C14—C15	1.478 (8)
S2—C11	1.747 (5)	C2—H2A	0.9300
O1—C4	1.365 (10)	C3—H3	0.9300
O1—C7	1.408 (10)	C5—H5	0.9300
O6—C14	1.207 (6)	C6—H6	0.9300
N1—C8	1.405 (5)	C7—H7A	0.9600
N2—C14	1.399 (7)	C7—H7B	0.9600
N1—H1	0.8600	C7—H7C	0.9600
N2—H2	0.8600	C9—H9	0.9300
C1—C6	1.359 (9)	C10—H10	0.9300
C1—C2	1.391 (8)	C12—H12	0.9300
C2—C3	1.357 (10)	C13—H13	0.9300
C3—C4	1.379 (11)	C15—H15A	0.9600
C4—C5	1.390 (9)	C15—H15B	0.9600
C5—C6	1.370 (9)	C15—H15C	0.9600

O2—S1—O3	120.2 (2)	S2—C11—C12	120.1 (3)
O2—S1—N1	109.0 (2)	C10—C11—C12	120.5 (4)
O2—S1—C1	107.7 (3)	C11—C12—C13	120.7 (4)
O3—S1—N1	104.9 (2)	C8—C13—C12	119.4 (5)
O3—S1—C1	107.6 (2)	O6—C14—C15	125.5 (5)
N1—S1—C1	106.8 (2)	N2—C14—C15	114.5 (4)
O4—S2—O5	119.9 (2)	O6—C14—N2	120.0 (5)
O4—S2—N2	102.2 (2)	C1—C2—H2A	120.00
O4—S2—C11	110.0 (2)	C3—C2—H2A	120.00
O5—S2—N2	108.8 (2)	C2—C3—H3	119.00
O5—S2—C11	108.0 (2)	C4—C3—H3	119.00
N2—S2—C11	107.2 (2)	C4—C5—H5	121.00
C4—O1—C7	119.0 (6)	C6—C5—H5	121.00
S1—N1—C8	128.4 (3)	C1—C6—H6	119.00
S2—N2—C14	124.4 (3)	C5—C6—H6	119.00
S1—N1—H1	116.00	O1—C7—H7A	109.00
C8—N1—H1	116.00	O1—C7—H7B	109.00
S2—N2—H2	118.00	O1—C7—H7C	109.00
C14—N2—H2	118.00	H7A—C7—H7B	110.00
S1—C1—C2	118.8 (5)	H7A—C7—H7C	110.00
S1—C1—C6	121.9 (4)	H7B—C7—H7C	110.00
C2—C1—C6	119.3 (6)	C8—C9—H9	120.00
C1—C2—C3	119.2 (6)	C10—C9—H9	120.00
C2—C3—C4	121.4 (6)	C9—C10—H10	121.00
O1—C4—C5	124.7 (7)	C11—C10—H10	121.00
C3—C4—C5	119.5 (7)	C11—C12—H12	120.00
O1—C4—C3	115.8 (6)	C13—C12—H12	120.00
C4—C5—C6	118.3 (6)	C8—C13—H13	120.00
C1—C6—C5	122.3 (6)	C12—C13—H13	120.00
C9—C8—C13	120.2 (4)	C14—C15—H15A	109.00
N1—C8—C9	116.8 (4)	C14—C15—H15B	109.00
N1—C8—C13	123.0 (4)	C14—C15—H15C	109.00
C8—C9—C10	120.5 (5)	H15A—C15—H15B	109.00
C9—C10—C11	118.8 (5)	H15A—C15—H15C	109.00
S2—C11—C10	119.4 (4)	H15B—C15—H15C	110.00

O2—S1—N1—C8	42.8 (5)	S2—N2—C14—O6	3.0 (7)
O3—S1—N1—C8	172.7 (4)	S2—N2—C14—C15	−175.4 (4)
C1—S1—N1—C8	−73.3 (5)	S1—C1—C2—C3	−178.1 (5)
O2—S1—C1—C2	171.0 (4)	C6—C1—C2—C3	−0.4 (8)
O2—S1—C1—C6	−6.7 (5)	S1—C1—C6—C5	178.2 (5)
O3—S1—C1—C2	40.0 (5)	C2—C1—C6—C5	0.6 (9)
O3—S1—C1—C6	−137.6 (5)	C1—C2—C3—C4	0.2 (9)
N1—S1—C1—C2	−72.1 (5)	C2—C3—C4—O1	−179.5 (6)
N1—S1—C1—C6	110.2 (5)	C2—C3—C4—C5	−0.2 (10)
O4—S2—N2—C14	176.6 (4)	O1—C4—C5—C6	179.6 (6)
O5—S2—N2—C14	48.9 (5)	C3—C4—C5—C6	0.3 (9)
C11—S2—N2—C14	−67.7 (4)	C4—C5—C6—C1	−0.5 (9)
O4—S2—C11—C10	30.0 (5)	N1—C8—C9—C10	178.9 (5)
O4—S2—C11—C12	−150.4 (4)	C13—C8—C9—C10	−0.7 (8)
O5—S2—C11—C10	162.5 (4)	N1—C8—C13—C12	−179.2 (4)
O5—S2—C11—C12	−17.9 (4)	C9—C8—C13—C12	0.4 (8)
N2—S2—C11—C10	−80.4 (4)	C8—C9—C10—C11	0.0 (8)
N2—S2—C11—C12	99.2 (4)	C9—C10—C11—S2	−179.4 (4)
C7—O1—C4—C3	178.1 (6)	C9—C10—C11—C12	1.1 (8)
C7—O1—C4—C5	−1.2 (9)	S2—C11—C12—C13	179.0 (4)
S1—N1—C8—C9	169.1 (4)	C10—C11—C12—C13	−1.4 (7)
S1—N1—C8—C13	−11.4 (7)	C11—C12—C13—C8	0.7 (8)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4ⁱ	0.86	2.09	2.932 (5)	168
N2—H2···O5ⁱⁱ	0.86	2.26	3.071 (5)	157
C13—H13···O2	0.93	2.35	2.986 (6)	126
C15—H15C···O6ⁱⁱ	0.96	2.45	3.348 (7)	156
C15—H15B···Cg1ⁱⁱⁱ	0.96	2.79	3.722 (6)	164
C15—H15A···Cg2ⁱⁱⁱ	0.96	2.79	3.589 (6)	141

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₆N₂O₆S₂
M_r	384.44
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	5.3651 (10), 20.551 (3), 15.034 (2)
β (°)	94.040 (7)
V (Å³)	1653.5 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.36
Crystal size (mm)	0.25 × 0.08 × 0.07

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	13678, 3771, 1608
R_int	0.114
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.084, 0.189, 0.89
No. of reflections	3771
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.83, −0.32

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4ⁱ	0.86	2.09	2.932 (5)	168
N2—H2···O5ⁱⁱ	0.86	2.26	3.071 (5)	157
C13—H13···O2	0.93	2.35	2.986 (6)	126
C15—H15C···O6ⁱⁱ	0.96	2.45	3.348 (7)	156
C15—H15B···Cg1ⁱⁱⁱ	0.96	2.79	3.722 (6)	164
C15—H15A···Cg2ⁱⁱⁱ	0.96	2.79	3.589 (6)	141

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

Acknowledgements

GM greatly acknowledge the Vice Chancellor, University of Gujrat, Professor Dr Nizam Uddin, for creating a healthy research environment in the University of Gujrat.

References

Ashfaq, M., Khan, I. U., Arshad, M. N., Ahmad, H. & Asghar, M. N. (2010). Acta Cryst. E66, o299. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Bruker (2007). APEX2 and SAINT. 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
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

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Volume 66| Part 7| July 2010| Page o1768

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