2-(6-Meth­oxy­naphthalen-2-yl)-1-(morpholin-4-yl)propan-1-one

Nasirullah; Islam, N.U.; Tahir, M.N.; Khan, I.; Zulfiqar, M.

doi:10.1107/S1600536812034083

organic compounds

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ISSN: 2056-9890

Volume 68| Part 9| September 2012| Page o2636

doi:10.1107/S1600536812034083

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2-(6-Methoxynaphthalen-2-yl)-1-(morpholin-4-yl)propan-1-one

Nasirullah,^a Nazar Ul Islam,^a M. Nawaz Tahir,^b ^* Ikhtiar Khan ^a and Muhammad Zulfiqar ^b

^aInstitute of Chemical Sciences, University of Peshawar, Peshawar, Pakistan, and ^bUniversity of Sargodha, Department of Physics, Sargodha, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 22 July 2012; accepted 31 July 2012; online 4 August 2012)

In the title compound, C₁₈H₂₁NO₃, the naphthalene group and the basal plane of the morpholine ring (r.m.s. deviations = 0.0177 and 0.0069 Å, respectively) are oriented at a dihedral angle of 44.0 (2)°. In the crystal, molecules are linked by C—H⋯π interactions.

Related literature

For the crystal structure of the related compound, naproxen [systematic name: (+)-2-(6-methoxy-2-naphthyl)-propionic acid], see: Ravikumar et al. (1985 ).

Experimental

Crystal data

C₁₈H₂₁NO₃
M_r = 299.36
Monoclinic, P 2₁
a = 9.5947 (15) Å
b = 6.6293 (8) Å
c = 12.340 (2) Å
β = 92.221 (5)°
V = 784.3 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.33 × 0.23 × 0.17 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.972, T_max = 0.986
6522 measured reflections
1681 independent reflections
1029 reflections with I > 2σ(I)
R_int = 0.047

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.142
S = 1.02
1681 reflections
201 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the C1–C6 and C3/C4/C7–C10 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯Cg3ⁱ	0.93	2.98	3.679 (5)	133
C15—H15A⋯Cg3ⁱⁱ	0.97	2.95	3.756 (5)	141
C16—H16A⋯Cg2ⁱⁱ	0.97	2.79	3.675 (5)	153
Symmetry codes: (i) $[-x+2, y+{\script{1\over 2}}, -z]$ ; (ii) x-1, y, z.

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); 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 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812034083/su2485sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812034083/su2485Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812034083/su2485Isup3.cml

checkCIF report

Comment top

The title compound is the morpholine derivative of Naproxen [(+)-2-(6-methoxy-2-naphthyl)-propionic acid], whose crystal structure has been reported on by (Ravikumar et al., 1985). The title compound was synthesized in order to study its biological properties and we report herein on its synthesis and crystal structure.

The molecular structure of the title compound is illustrated in Fig. 1. The naphthaline group A (C1–C10) and the basal plane of the morpholine group B (atoms C15—C18) are planar with r.m.s. deviations of 0.0177 Å and 0.0069 Å, respectively. The dihedral angle between planes A/B is 43.97 (23)°. The O1 and C11 atoms of the methoxy group are at a distance of -0.0911 (44) and -0.2335 (74) Å, respectively, from the mean plane of the naphthaline group. The morpholine group has a chair conformation with atoms N1 and O3 at a distance of 0.5827 (79) and -0.6752 (77) Å, respectively, from the basal plane B.

In the crystal, molecules are linked via C—H···π interactions (Table 1).

Related literature top

For the crystal structure of the related compound, naproxen [systematic name: (+)-2-(6-methoxy-2-naphthyl)-propionic acid], see: Ravikumar et al. (1985).

Experimental top

A solution of morpholine (0.35 g, 40.2 mmol) in 5 ml of dichloromethane (DCM) was added to a solution of naproxen acid chloride (0.5 g, 20.1 mmol) in DCM (10 ml). The reaction mixture was stirred at room temperature for 3 h. After completion the reaction mixture was filtered and the filtrate concentrated to give the crude product. The product was purified by flash column chromatogrphy using n-hexane: ethyl acetate (50:50). The resulting jelly like product was recystallized from diethyl ether and hexane (1:1) to give the title compound as colourless prism-like crystals, suitable for X-ray diffraction analysis [Yield: 65.0%, M.p.: 388 K].

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

Fig. 1. A view of the molecular structure of the title molecule, with atom numbering. Displacement ellipsoids are drawn at the 50% probability level.

2-(6-Methoxynaphthalen-2-yl)-1-(morpholin-4-yl)propan-1-one top

Crystal data top

C₁₈H₂₁NO₃	F(000) = 320
M_r = 299.36	D_x = 1.268 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1029 reflections
a = 9.5947 (15) Å	θ = 1.7–26.0°
b = 6.6293 (8) Å	µ = 0.09 mm⁻¹
c = 12.340 (2) Å	T = 296 K
β = 92.221 (5)°	Prism, colourless
V = 784.3 (2) Å³	0.33 × 0.23 × 0.17 mm
Z = 2

Data collection top

Bruker Kappa APEXII CCD diffractometer	1681 independent reflections
Radiation source: fine-focus sealed tube	1029 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
Detector resolution: 8.00 pixels mm^-1	θ_max = 26.0°, θ_min = 1.7°
ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −8→7
T_min = 0.972, T_max = 0.986	l = −15→15
6522 measured reflections

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.142	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0707P)²] where P = (F_o² + 2F_c²)/3
1681 reflections	(Δ/σ)_max < 0.001
201 parameters	Δρ_max = 0.18 e Å⁻³
1 restraint	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₈H₂₁NO₃	V = 784.3 (2) Å³
M_r = 299.36	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 9.5947 (15) Å	µ = 0.09 mm⁻¹
b = 6.6293 (8) Å	T = 296 K
c = 12.340 (2) Å	0.33 × 0.23 × 0.17 mm
β = 92.221 (5)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	1681 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1029 reflections with I > 2σ(I)
T_min = 0.972, T_max = 0.986	R_int = 0.047
6522 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	1 restraint
wR(F²) = 0.142	H-atom parameters constrained
S = 1.02	Δρ_max = 0.18 e Å⁻³
1681 reflections	Δρ_min = −0.19 e Å⁻³
201 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 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
O1	1.3551 (3)	0.2256 (4)	−0.0544 (3)	0.0602 (11)
O2	0.6416 (3)	0.3801 (5)	0.3319 (3)	0.0829 (16)
O3	0.2888 (3)	0.8958 (5)	0.3399 (3)	0.0884 (14)
N1	0.5373 (4)	0.6801 (5)	0.3199 (3)	0.0609 (14)
C1	0.9024 (4)	0.5452 (6)	0.2733 (3)	0.0465 (16)
C2	0.9648 (4)	0.6297 (6)	0.1868 (3)	0.0460 (14)
C3	1.0673 (4)	0.5277 (6)	0.1281 (3)	0.0425 (14)
C4	1.1077 (4)	0.3316 (6)	0.1603 (3)	0.0436 (16)
C5	1.0438 (4)	0.2470 (6)	0.2511 (4)	0.0513 (14)
C6	0.9445 (4)	0.3484 (6)	0.3041 (4)	0.0530 (17)
C7	1.1283 (4)	0.6141 (7)	0.0367 (4)	0.0511 (14)
C8	1.2234 (4)	0.5100 (7)	−0.0192 (3)	0.0533 (17)
C9	1.2619 (4)	0.3142 (7)	0.0120 (4)	0.0496 (16)
C10	1.2068 (4)	0.2259 (6)	0.1004 (3)	0.0482 (14)
C11	1.3915 (5)	0.0220 (7)	−0.0360 (5)	0.081 (2)
C12	0.7953 (4)	0.6652 (7)	0.3314 (4)	0.0522 (16)
C13	0.8407 (5)	0.7042 (9)	0.4502 (4)	0.079 (2)
C14	0.6520 (4)	0.5624 (7)	0.3276 (4)	0.0573 (19)
C15	0.3990 (4)	0.5883 (8)	0.3042 (5)	0.083 (2)
C16	0.2948 (5)	0.6889 (8)	0.3671 (5)	0.074 (2)
C17	0.4198 (5)	0.9877 (8)	0.3664 (6)	0.093 (3)
C18	0.5324 (5)	0.8992 (7)	0.3048 (5)	0.076 (2)
H2	0.93901	0.75949	0.16555	0.0550*
H5	1.07044	0.11908	0.27494	0.0613*
H6	0.90287	0.28688	0.36230	0.0634*
H7	1.10287	0.74354	0.01461	0.0612*
H8	1.26357	0.56916	−0.07875	0.0638*
H10	1.23423	0.09657	0.12116	0.0575*
H11A	1.43560	0.00846	0.03477	0.1220*
H11B	1.45462	−0.02119	−0.08983	0.1220*
H11C	1.30890	−0.05985	−0.04048	0.1220*
H12	0.78519	0.79615	0.29504	0.0627*
H13A	0.84608	0.57838	0.48862	0.1191*
H13B	0.77382	0.79042	0.48299	0.1191*
H13C	0.93047	0.76826	0.45328	0.1191*
H15A	0.37086	0.59422	0.22793	0.0991*
H15B	0.40414	0.44741	0.32518	0.0991*
H16A	0.20434	0.62728	0.35244	0.0888*
H16B	0.31828	0.67402	0.44387	0.0888*
H17A	0.44130	0.97154	0.44335	0.1111*
H17B	0.41381	1.13106	0.35108	0.1111*
H18A	0.51725	0.92988	0.22838	0.0903*
H18B	0.62088	0.95783	0.32891	0.0903*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0555 (18)	0.053 (2)	0.073 (2)	0.0001 (15)	0.0157 (16)	−0.0012 (16)
O2	0.052 (2)	0.039 (2)	0.158 (4)	0.0020 (15)	0.009 (2)	0.000 (2)
O3	0.062 (2)	0.056 (2)	0.147 (3)	0.0147 (17)	0.002 (2)	0.007 (2)
N1	0.044 (2)	0.037 (2)	0.102 (3)	0.0007 (17)	0.007 (2)	−0.0035 (19)
C1	0.036 (2)	0.050 (3)	0.053 (3)	0.000 (2)	−0.004 (2)	−0.003 (2)
C2	0.040 (2)	0.037 (2)	0.060 (3)	−0.0007 (19)	−0.010 (2)	0.003 (2)
C3	0.037 (2)	0.042 (2)	0.048 (3)	0.0008 (19)	−0.0062 (19)	0.0000 (19)
C4	0.036 (2)	0.046 (3)	0.048 (3)	−0.0011 (18)	−0.007 (2)	0.004 (2)
C5	0.048 (2)	0.038 (2)	0.068 (3)	0.0066 (19)	0.003 (2)	0.008 (2)
C6	0.054 (3)	0.050 (3)	0.055 (3)	0.004 (2)	0.001 (2)	0.010 (2)
C7	0.046 (2)	0.040 (2)	0.067 (3)	−0.004 (2)	−0.003 (2)	0.007 (2)
C8	0.052 (3)	0.054 (3)	0.054 (3)	−0.009 (2)	0.004 (2)	0.006 (2)
C9	0.044 (2)	0.049 (3)	0.056 (3)	−0.006 (2)	0.003 (2)	−0.009 (2)
C10	0.042 (2)	0.044 (2)	0.058 (3)	0.0044 (19)	−0.004 (2)	0.001 (2)
C11	0.079 (4)	0.063 (4)	0.104 (4)	0.026 (3)	0.037 (3)	0.016 (3)
C12	0.042 (2)	0.049 (3)	0.066 (3)	0.002 (2)	0.007 (2)	−0.004 (2)
C13	0.064 (3)	0.099 (4)	0.075 (4)	−0.007 (3)	0.000 (3)	−0.029 (3)
C14	0.048 (3)	0.043 (3)	0.081 (4)	0.001 (2)	0.004 (2)	−0.003 (2)
C15	0.044 (3)	0.060 (4)	0.144 (5)	−0.004 (2)	0.002 (3)	−0.012 (3)
C16	0.046 (3)	0.065 (4)	0.111 (4)	−0.001 (3)	−0.001 (3)	0.003 (3)
C17	0.067 (4)	0.048 (3)	0.165 (6)	0.000 (3)	0.023 (4)	−0.010 (4)
C18	0.062 (3)	0.047 (3)	0.119 (5)	0.007 (2)	0.023 (3)	0.012 (3)

Geometric parameters (Å, º) top

O1—C9	1.369 (5)	C17—C18	1.467 (8)
O1—C11	1.410 (5)	C2—H2	0.9300
O2—C14	1.214 (6)	C5—H5	0.9300
O3—C16	1.413 (6)	C6—H6	0.9300
O3—C17	1.423 (6)	C7—H7	0.9300
N1—C14	1.349 (6)	C8—H8	0.9300
N1—C15	1.466 (6)	C10—H10	0.9300
N1—C18	1.465 (6)	C11—H11A	0.9600
C1—C2	1.364 (5)	C11—H11B	0.9600
C1—C6	1.413 (6)	C11—H11C	0.9600
C1—C12	1.503 (6)	C12—H12	0.9800
C2—C3	1.416 (5)	C13—H13A	0.9600
C3—C4	1.409 (6)	C13—H13B	0.9600
C3—C7	1.412 (6)	C13—H13C	0.9600
C4—C5	1.414 (6)	C15—H15A	0.9700
C4—C10	1.413 (5)	C15—H15B	0.9700
C5—C6	1.355 (6)	C16—H16A	0.9700
C7—C8	1.354 (6)	C16—H16B	0.9700
C8—C9	1.400 (6)	C17—H17A	0.9700
C9—C10	1.363 (6)	C17—H17B	0.9700
C12—C13	1.535 (7)	C18—H18A	0.9700
C12—C14	1.534 (6)	C18—H18B	0.9700
C15—C16	1.452 (7)

C9—O1—C11	118.5 (4)	C8—C7—H7	120.00
C16—O3—C17	109.5 (4)	C7—C8—H8	120.00
C14—N1—C15	120.1 (4)	C9—C8—H8	120.00
C14—N1—C18	127.2 (4)	C4—C10—H10	120.00
C15—N1—C18	111.7 (4)	C9—C10—H10	120.00
C2—C1—C6	117.4 (4)	O1—C11—H11A	109.00
C2—C1—C12	119.0 (4)	O1—C11—H11B	109.00
C6—C1—C12	123.6 (4)	O1—C11—H11C	109.00
C1—C2—C3	122.6 (4)	H11A—C11—H11B	110.00
C2—C3—C4	119.0 (3)	H11A—C11—H11C	109.00
C2—C3—C7	122.2 (4)	H11B—C11—H11C	109.00
C4—C3—C7	118.8 (4)	C1—C12—H12	108.00
C3—C4—C5	117.8 (3)	C13—C12—H12	108.00
C3—C4—C10	119.6 (3)	C14—C12—H12	108.00
C5—C4—C10	122.6 (4)	C12—C13—H13A	109.00
C4—C5—C6	121.4 (4)	C12—C13—H13B	109.00
C1—C6—C5	121.8 (4)	C12—C13—H13C	109.00
C3—C7—C8	120.6 (4)	H13A—C13—H13B	109.00
C7—C8—C9	120.6 (4)	H13A—C13—H13C	110.00
O1—C9—C8	113.9 (4)	H13B—C13—H13C	109.00
O1—C9—C10	125.3 (4)	N1—C15—H15A	109.00
C8—C9—C10	120.8 (4)	N1—C15—H15B	109.00
C4—C10—C9	119.7 (4)	C16—C15—H15A	109.00
C1—C12—C13	111.8 (4)	C16—C15—H15B	109.00
C1—C12—C14	112.3 (4)	H15A—C15—H15B	108.00
C13—C12—C14	109.0 (4)	O3—C16—H16A	110.00
O2—C14—N1	120.7 (4)	O3—C16—H16B	110.00
O2—C14—C12	121.1 (4)	C15—C16—H16A	110.00
N1—C14—C12	118.2 (4)	C15—C16—H16B	110.00
N1—C15—C16	112.2 (4)	H16A—C16—H16B	108.00
O3—C16—C15	110.0 (4)	O3—C17—H17A	109.00
O3—C17—C18	111.8 (5)	O3—C17—H17B	109.00
N1—C18—C17	110.6 (4)	C18—C17—H17A	109.00
C1—C2—H2	119.00	C18—C17—H17B	109.00
C3—C2—H2	119.00	H17A—C17—H17B	108.00
C4—C5—H5	119.00	N1—C18—H18A	110.00
C6—C5—H5	119.00	N1—C18—H18B	110.00
C1—C6—H6	119.00	C17—C18—H18A	110.00
C5—C6—H6	119.00	C17—C18—H18B	110.00
C3—C7—H7	120.00	H18A—C18—H18B	108.00

C11—O1—C9—C10	4.6 (6)	C4—C3—C7—C8	0.3 (6)
C11—O1—C9—C8	−174.5 (4)	C7—C3—C4—C10	−0.5 (6)
C17—O3—C16—C15	−62.1 (6)	C2—C3—C7—C8	−178.3 (4)
C16—O3—C17—C18	61.9 (6)	C7—C3—C4—C5	−179.1 (4)
C18—N1—C15—C16	−50.5 (6)	C2—C3—C4—C5	−0.5 (6)
C14—N1—C15—C16	140.2 (5)	C2—C3—C4—C10	178.1 (4)
C18—N1—C14—O2	−174.4 (5)	C3—C4—C5—C6	1.6 (6)
C18—N1—C14—C12	5.9 (7)	C3—C4—C10—C9	−0.2 (6)
C15—N1—C14—O2	−7.0 (7)	C5—C4—C10—C9	178.3 (4)
C15—N1—C18—C17	48.5 (6)	C10—C4—C5—C6	−177.0 (4)
C14—N1—C18—C17	−143.2 (5)	C4—C5—C6—C1	−1.7 (7)
C15—N1—C14—C12	173.4 (4)	C3—C7—C8—C9	0.6 (6)
C6—C1—C12—C14	−61.7 (5)	C7—C8—C9—C10	−1.4 (6)
C6—C1—C2—C3	0.4 (6)	C7—C8—C9—O1	177.8 (4)
C2—C1—C12—C13	−118.0 (4)	O1—C9—C10—C4	−177.9 (4)
C6—C1—C12—C13	61.1 (5)	C8—C9—C10—C4	1.1 (6)
C12—C1—C6—C5	−178.4 (4)	C13—C12—C14—N1	91.2 (5)
C2—C1—C12—C14	119.2 (4)	C13—C12—C14—O2	−88.5 (6)
C2—C1—C6—C5	0.7 (6)	C1—C12—C14—N1	−144.5 (4)
C12—C1—C2—C3	179.6 (4)	C1—C12—C14—O2	35.8 (6)
C1—C2—C3—C7	178.1 (4)	N1—C15—C16—O3	57.1 (6)
C1—C2—C3—C4	−0.5 (6)	O3—C17—C18—N1	−54.8 (6)

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg3 are the centroids of the C1–C6 and C3/C4/C7–C10 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···Cg3ⁱ	0.93	2.98	3.679 (5)	133
C15—H15A···Cg3ⁱⁱ	0.97	2.95	3.756 (5)	141
C16—H16A···Cg2ⁱⁱ	0.97	2.79	3.675 (5)	153

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

Experimental details

Crystal data
Chemical formula	C₁₈H₂₁NO₃
M_r	299.36
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	296
a, b, c (Å)	9.5947 (15), 6.6293 (8), 12.340 (2)
β (°)	92.221 (5)
V (Å³)	784.3 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.33 × 0.23 × 0.17

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.972, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	6522, 1681, 1029
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.142, 1.02
No. of reflections	1681
No. of parameters	201
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.19

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

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg3 are the centroids of the C1–C6 and C3/C4/C7–C10 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···Cg3ⁱ	0.93	2.98	3.679 (5)	133
C15—H15A···Cg3ⁱⁱ	0.97	2.95	3.756 (5)	141
C16—H16A···Cg2ⁱⁱ	0.97	2.79	3.675 (5)	153

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

Acknowledgements

The authors acknowledge the provision of funds for the purchase of a diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan. They also acknowledge the technical support provided by Syed Muhammad Hussain Rizvi of Bana International, Karachi, Pakistan.

References

Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2009). 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
Ravikumar, K., Rajan, S. S., Pattabhi, V. & Gabe, E. J. (1985). Acta Cryst. C41, 280–282. CSD CrossRef CAS Web of Science 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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ISSN: 2056-9890

Volume 68| Part 9| September 2012| Page o2636

doi:10.1107/S1600536812034083

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