2-(4-Chloro­phen­yl)-6-methyl-4-(3-methyl­phen­yl)quinoline

Prabhuswamy, M.; Swaroop, T.R.; Madan Kumar, S.; Rangappa, K.S.; Lokanath, N.K.

doi:10.1107/S1600536812043954

organic compounds

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page o3250

doi:10.1107/S1600536812043954

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2-(4-Chlorophenyl)-6-methyl-4-(3-methylphenyl)quinoline

M Prabhuswamy,^a T. R. Swaroop,^b S. Madan Kumar,^a K. S. Rangappa ^b and N. K. Lokanath ^a ^*

^aDepartment of Studies in Physics, Manasagangotri, University of Mysore, Mysore 570 006, India, and ^bDepartment of Studies in Chemistry, Manasagangotri, University of Mysore, Mysore 570 006, India
^*Correspondence e-mail: lokanath@physics.uni-mysore.ac.in

(Received 13 October 2012; accepted 23 October 2012; online 31 October 2012)

In the title compound, C₂₃H₁₈ClN, the dihedral angles between the quinoline unit and the chlorobenzene and methylbenzene rings are 2.57 (9) and 56.06 (9)°, respectively. The crystal structure is stabilized by π–π interactions [minimum ring centroid separation = 3.733 (2) Å].

Related literature

For quinolines, see: Michael (1997 ); Balasubramanian et al. (1996 ). For a related structure, see: Asiri et al. (2011 ).

Experimental

Crystal data

C₂₃H₁₈ClN
M_r = 343.83
Monoclinic, P 2₁ /c
a = 7.982 (3) Å
b = 17.921 (6) Å
c = 12.478 (4) Å
β = 92.581 (6)°
V = 1783.1 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 293 K
0.23 × 0.22 × 0.22 mm

Data collection

Oxford Diffraction Xcalibur CCD diffractometer
16998 measured reflections
3392 independent reflections
2508 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.168
S = 1.04
3392 reflections
228 parameters
H-atom parameters constrained
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.45 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812043954/zs2238sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812043954/zs2238Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812043954/zs2238Isup3.cml

checkCIF report

Comment top

Quinolines and their derivatives occur in numerous natural products (Michael, 1997) and may exhibit interesting physiochemical activities, finding applications as pharmaceuticals and agrochemicals as well as being general synthetic platforms (Balasubramanian et al., 1996).

In the title molecule, C₂₃ H₁₈ Cl N, (Fig. 1), dihedral angles between the quinoline moiety and the chlorobenzene and methylbenzene rings are 2.57 (9) and 56.06 (9)°, respectively, with the conformation of the chlorobenzene ring influenced by the presence of an intramolecular C5—H···N1 interaction [2.764 (3) Å]. The overall geometry of the title compound is similar to 4-(4-chlorophenyl)-8-methyl-2-oxo-1,2,5,6,7,8-hexahydroquinoline -3-carbonitrile (Asiri et al., 2011).

The crystal structure (Fig. 2) is stabilized by aromatic ring π··· π interactions with the ring centroids defined as follows: Cg(1), N1/C7/C8/C9/C10/C15; Cg(2), C1/C2/C3/C4/C5/C6 and Cg(3), C10/C11/C12/C13/C14/C15. The distance between Cg(1) and Cg(1) is 3.7427 (18) Å [-x+3, -y+2, -z+1], Cg(1) and Cg(2) is 3.7679 (19) Å [-x+2,-y+2,1 -z], Cg(1) and Cg(3) is 3.7635 (18) Å [-x+3, -y+2, -z+1], Cg(2) and Cg(3) is 3.733 (2) Å [-x+2, -y+2, -z+1].

Related literature top

For quinolines, see: Michael (1997); Balasubramanian et al. (1996). For a related structure, see: Asiri et al. (2011).

Experimental top

The enaminone [3-(4-chlorophenyl)-1-m-tolyl-3-(p-tolyamino)prop-2-en-1-one] (5 mmol) was taken in polyphosphoric acid (5 mL) and heated at 140 °C for 5 h. After completion of the reaction (monitored by TLC), the reaction mixture was diluted with water (50 mL). The aqueous layer was extracted with ethyl acetate (3 x 20 mL), the combined ethyl acetate layer was washed with 0.1 N NaOH (2 x 25 mL), followed by brine solution (25 mL). The organic layer was then dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford the crude product which was purified by column chromatography over silica gel (60–120 mesh) using a hexane:ethyl acetate mixture (9.5:0.5) as eluent. The pure title compound was crystallized in an ethyl acetate–hexane mixture to obtain pale yellow single crystals. ¹H NMR (CDCl₃, 300 MHz): 8.49 (d, 2H, J=8.4 Hz), 7.92 (d, 1H, J=7.2 Hz), 7.79 (s, 1H), 7.55–7.66 (m, 5H), 7.19 (d, 1H), 2.34 (s, 3H), 2.35 (s, 3H). Mass: Calc. 343.2 found 344.2 (M⁺+1): m.p. 98–100 °C (uncorrected).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. ORTEP diagram of the title compound showing 50% probability ellipsoids.
	Fig. 2. A packing diagram of the title compound, viewed along the crystallographic a axis.

2-(4-Chlorophenyl)-6-methyl-4-(3-methylphenyl)quinoline top

Crystal data top

C₂₃H₁₈ClN	F(000) = 720
M_r = 343.83	D_x = 1.281 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 371–373 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.982 (3) Å	Cell parameters from 3392 reflections
b = 17.921 (6) Å	θ = 2.0–25.7°
c = 12.478 (4) Å	µ = 0.22 mm⁻¹
β = 92.581 (6)°	T = 293 K
V = 1783.1 (11) Å³	Block, yellow
Z = 4	0.23 × 0.22 × 0.22 mm

Data collection top

Oxford Diffraction Xcalibur CCD diffractometer	2508 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.044
Graphite monochromator	θ_max = 25.7°, θ_min = 2.0°
Detector resolution: 16.0839 pixels mm^-1	h = −9→9
ω scans	k = −21→21
16998 measured reflections	l = −15→15
3392 independent 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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.168	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0922P)² + 0.5751P] P = (F_o² + 2F_c²)/3
3392 reflections	(Δ/σ)_max = 0.001
228 parameters	Δρ_max = 0.49 e Å⁻³
0 restraints	Δρ_min = −0.45 e Å⁻³

Crystal data top

C₂₃H₁₈ClN	V = 1783.1 (11) Å³
M_r = 343.83	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.982 (3) Å	µ = 0.22 mm⁻¹
b = 17.921 (6) Å	T = 293 K
c = 12.478 (4) Å	0.23 × 0.22 × 0.22 mm
β = 92.581 (6)°

Data collection top

Oxford Diffraction Xcalibur CCD diffractometer	2508 reflections with I > 2σ(I)
16998 measured reflections	R_int = 0.044
3392 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.168	H-atom parameters constrained
S = 1.04	Δρ_max = 0.49 e Å⁻³
3392 reflections	Δρ_min = −0.45 e Å⁻³
228 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
Cl1	0.89231 (10)	1.22893 (5)	0.85463 (6)	0.0816 (3)
N1	1.2557 (2)	0.97450 (10)	0.55301 (13)	0.0406 (6)
C1	0.9786 (3)	1.17421 (15)	0.7563 (2)	0.0542 (8)
C2	0.9969 (4)	1.20263 (15)	0.6569 (2)	0.0640 (9)
C3	1.0682 (4)	1.15951 (14)	0.5796 (2)	0.0607 (9)
C4	1.1224 (3)	1.08789 (12)	0.60147 (17)	0.0404 (7)
C5	1.0989 (3)	1.06052 (14)	0.70260 (18)	0.0510 (8)
C6	1.0278 (3)	1.10238 (15)	0.7802 (2)	0.0590 (9)
C7	1.2017 (2)	1.04084 (11)	0.52008 (17)	0.0387 (6)
C8	1.2226 (3)	1.06583 (11)	0.41476 (17)	0.0411 (6)
C9	1.2984 (3)	1.02293 (11)	0.34173 (16)	0.0380 (6)
C10	1.3536 (2)	0.95017 (11)	0.37377 (16)	0.0369 (6)
C11	1.4245 (3)	0.89791 (11)	0.30488 (18)	0.0413 (7)
C12	1.4739 (3)	0.82860 (11)	0.33979 (19)	0.0451 (7)
C13	1.4533 (3)	0.81027 (12)	0.44755 (19)	0.0512 (8)
C14	1.3836 (3)	0.85844 (12)	0.51636 (19)	0.0486 (7)
C15	1.3289 (2)	0.92982 (11)	0.48076 (16)	0.0379 (6)
C16	1.3247 (3)	1.05256 (11)	0.23256 (16)	0.0417 (7)
C17	1.1911 (3)	1.08107 (13)	0.17090 (18)	0.0523 (8)
C18	1.2162 (4)	1.10960 (14)	0.0705 (2)	0.0630 (10)
C19	1.3729 (4)	1.11009 (13)	0.03096 (19)	0.0639 (9)
C20	1.5098 (4)	1.08379 (13)	0.0910 (2)	0.0555 (8)
C21	1.4827 (3)	1.05492 (11)	0.19201 (18)	0.0467 (7)
C22	1.6837 (4)	1.08762 (18)	0.0504 (3)	0.0827 (11)
C23	1.5477 (4)	0.77324 (13)	0.2648 (2)	0.0612 (9)
H2	0.96150	1.25100	0.64090	0.0770*
H3	1.07990	1.17910	0.51130	0.0730*
H5	1.13240	1.01200	0.71880	0.0610*
H6	1.01310	1.08260	0.84800	0.0710*
H8	1.18350	1.11290	0.39470	0.0490*
H11	1.43820	0.91080	0.23360	0.0500*
H13	1.48850	0.76370	0.47260	0.0610*
H14	1.37150	0.84460	0.58740	0.0580*
H17	1.08400	1.08090	0.19740	0.0630*
H18	1.12600	1.12860	0.02940	0.0750*
H19	1.38760	1.12850	−0.03770	0.0770*
H21	1.57340	1.03670	0.23350	0.0560*
H22A	1.75030	1.04790	0.08160	0.1240*
H22B	1.73340	1.13470	0.06980	0.1240*
H22C	1.67850	1.08260	−0.02630	0.1240*
H23A	1.47600	0.73030	0.25820	0.0920*
H23B	1.65660	0.75820	0.29280	0.0920*
H23C	1.55780	0.79580	0.19560	0.0920*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0855 (6)	0.0839 (6)	0.0764 (5)	0.0060 (4)	0.0149 (4)	−0.0363 (4)
N1	0.0447 (10)	0.0354 (9)	0.0415 (10)	−0.0025 (8)	0.0002 (8)	0.0039 (7)
C1	0.0449 (13)	0.0615 (16)	0.0562 (14)	−0.0035 (11)	0.0027 (11)	−0.0205 (12)
C2	0.0766 (18)	0.0471 (14)	0.0690 (17)	0.0126 (13)	0.0111 (14)	−0.0059 (13)
C3	0.0819 (19)	0.0481 (14)	0.0527 (14)	0.0151 (13)	0.0097 (13)	0.0048 (11)
C4	0.0347 (11)	0.0415 (12)	0.0448 (12)	−0.0022 (9)	−0.0009 (9)	−0.0023 (9)
C5	0.0576 (14)	0.0497 (13)	0.0457 (13)	0.0044 (11)	0.0039 (10)	0.0013 (10)
C6	0.0653 (16)	0.0642 (16)	0.0477 (13)	0.0006 (13)	0.0060 (12)	−0.0022 (11)
C7	0.0359 (11)	0.0364 (11)	0.0433 (11)	−0.0029 (8)	−0.0032 (9)	0.0012 (9)
C8	0.0463 (12)	0.0325 (10)	0.0441 (11)	0.0039 (9)	−0.0012 (9)	0.0032 (9)
C9	0.0396 (11)	0.0340 (10)	0.0401 (11)	−0.0022 (9)	−0.0026 (9)	0.0023 (8)
C10	0.0356 (11)	0.0307 (10)	0.0438 (11)	−0.0037 (8)	−0.0036 (8)	0.0026 (8)
C11	0.0454 (12)	0.0345 (11)	0.0440 (11)	−0.0031 (9)	0.0015 (9)	0.0000 (9)
C12	0.0448 (13)	0.0326 (11)	0.0576 (13)	−0.0005 (9)	−0.0018 (10)	−0.0033 (10)
C13	0.0620 (15)	0.0300 (11)	0.0612 (15)	0.0031 (10)	−0.0007 (12)	0.0081 (10)
C14	0.0601 (14)	0.0359 (11)	0.0496 (13)	−0.0009 (10)	−0.0005 (11)	0.0109 (9)
C15	0.0370 (11)	0.0322 (10)	0.0441 (11)	−0.0042 (8)	−0.0016 (9)	0.0030 (8)
C16	0.0567 (13)	0.0268 (10)	0.0415 (11)	0.0019 (9)	0.0021 (10)	0.0002 (8)
C17	0.0626 (16)	0.0441 (13)	0.0495 (13)	0.0051 (11)	−0.0037 (11)	0.0025 (10)
C18	0.089 (2)	0.0514 (15)	0.0472 (14)	0.0086 (13)	−0.0120 (14)	0.0055 (11)
C19	0.112 (2)	0.0409 (13)	0.0391 (12)	−0.0041 (14)	0.0070 (14)	0.0062 (10)
C20	0.0813 (18)	0.0334 (11)	0.0529 (14)	−0.0071 (11)	0.0155 (13)	−0.0022 (10)
C21	0.0614 (14)	0.0315 (11)	0.0476 (12)	0.0009 (10)	0.0061 (10)	0.0026 (9)
C22	0.102 (2)	0.0675 (18)	0.082 (2)	−0.0143 (17)	0.0404 (18)	0.0048 (16)
C23	0.0752 (18)	0.0396 (13)	0.0686 (17)	0.0096 (12)	0.0006 (14)	−0.0068 (11)

Geometric parameters (Å, º) top

Cl1—C1	1.737 (3)	C17—C18	1.376 (3)
N1—C7	1.324 (3)	C18—C19	1.365 (4)
N1—C15	1.358 (3)	C19—C20	1.380 (4)
C1—C2	1.355 (4)	C20—C21	1.388 (3)
C1—C6	1.375 (4)	C20—C22	1.501 (5)
C2—C3	1.379 (4)	C2—H2	0.9300
C3—C4	1.378 (3)	C3—H3	0.9300
C4—C5	1.375 (3)	C5—H5	0.9300
C4—C7	1.484 (3)	C6—H6	0.9300
C5—C6	1.368 (3)	C8—H8	0.9300
C7—C8	1.405 (3)	C11—H11	0.9300
C8—C9	1.355 (3)	C13—H13	0.9300
C9—C10	1.428 (3)	C14—H14	0.9300
C9—C16	1.486 (3)	C17—H17	0.9300
C10—C11	1.407 (3)	C18—H18	0.9300
C10—C15	1.406 (3)	C19—H19	0.9300
C11—C12	1.368 (3)	C21—H21	0.9300
C12—C13	1.401 (3)	C22—H22A	0.9600
C12—C23	1.502 (3)	C22—H22B	0.9600
C13—C14	1.355 (3)	C22—H22C	0.9600
C14—C15	1.417 (3)	C23—H23A	0.9600
C16—C17	1.384 (3)	C23—H23B	0.9600
C16—C21	1.381 (3)	C23—H23C	0.9600

C7—N1—C15	117.87 (17)	C21—C20—C22	120.5 (3)
Cl1—C1—C2	119.8 (2)	C16—C21—C20	121.8 (2)
Cl1—C1—C6	119.60 (19)	C1—C2—H2	120.00
C2—C1—C6	120.6 (2)	C3—C2—H2	120.00
C1—C2—C3	119.7 (2)	C2—C3—H3	119.00
C2—C3—C4	121.3 (2)	C4—C3—H3	119.00
C3—C4—C5	117.4 (2)	C4—C5—H5	119.00
C3—C4—C7	122.3 (2)	C6—C5—H5	119.00
C5—C4—C7	120.4 (2)	C1—C6—H6	121.00
C4—C5—C6	122.2 (2)	C5—C6—H6	121.00
C1—C6—C5	118.9 (2)	C7—C8—H8	119.00
N1—C7—C4	116.17 (18)	C9—C8—H8	119.00
N1—C7—C8	121.72 (18)	C10—C11—H11	119.00
C4—C7—C8	122.09 (18)	C12—C11—H11	119.00
C7—C8—C9	121.55 (19)	C12—C13—H13	119.00
C8—C9—C10	118.12 (18)	C14—C13—H13	119.00
C8—C9—C16	119.97 (18)	C13—C14—H14	120.00
C10—C9—C16	121.91 (18)	C15—C14—H14	120.00
C9—C10—C11	124.36 (19)	C16—C17—H17	120.00
C9—C10—C15	116.61 (17)	C18—C17—H17	120.00
C11—C10—C15	119.00 (18)	C17—C18—H18	120.00
C10—C11—C12	121.9 (2)	C19—C18—H18	120.00
C11—C12—C13	118.3 (2)	C18—C19—H19	119.00
C11—C12—C23	121.1 (2)	C20—C19—H19	119.00
C13—C12—C23	120.61 (19)	C16—C21—H21	119.00
C12—C13—C14	121.9 (2)	C20—C21—H21	119.00
C13—C14—C15	120.4 (2)	C20—C22—H22A	109.00
N1—C15—C10	124.08 (18)	C20—C22—H22B	109.00
N1—C15—C14	117.40 (18)	C20—C22—H22C	109.00
C10—C15—C14	118.52 (18)	H22A—C22—H22B	110.00
C9—C16—C17	120.3 (2)	H22A—C22—H22C	109.00
C9—C16—C21	121.1 (2)	H22B—C22—H22C	109.00
C17—C16—C21	118.6 (2)	C12—C23—H23A	109.00
C16—C17—C18	120.2 (2)	C12—C23—H23B	109.00
C17—C18—C19	120.3 (3)	C12—C23—H23C	109.00
C18—C19—C20	121.2 (2)	H23A—C23—H23B	109.00
C19—C20—C21	117.9 (3)	H23A—C23—H23C	110.00
C19—C20—C22	121.5 (2)	H23B—C23—H23C	110.00

C15—N1—C7—C8	−1.7 (3)	C8—C9—C10—C11	175.9 (2)
C7—N1—C15—C14	−178.93 (18)	C10—C9—C16—C21	−54.9 (3)
C7—N1—C15—C10	1.2 (3)	C10—C9—C16—C17	127.5 (2)
C15—N1—C7—C4	179.95 (17)	C15—C10—C11—C12	−1.7 (3)
Cl1—C1—C6—C5	−178.59 (19)	C9—C10—C15—N1	0.6 (3)
Cl1—C1—C2—C3	178.8 (2)	C11—C10—C15—N1	−177.30 (18)
C6—C1—C2—C3	−1.1 (4)	C11—C10—C15—C14	2.8 (3)
C2—C1—C6—C5	1.4 (4)	C9—C10—C15—C14	−179.27 (19)
C1—C2—C3—C4	−0.4 (5)	C9—C10—C11—C12	−179.4 (2)
C2—C3—C4—C7	−179.1 (2)	C10—C11—C12—C23	179.4 (2)
C2—C3—C4—C5	1.5 (4)	C10—C11—C12—C13	−0.4 (3)
C3—C4—C7—N1	176.7 (2)	C23—C12—C13—C14	−178.5 (2)
C5—C4—C7—C8	177.7 (2)	C11—C12—C13—C14	1.3 (4)
C5—C4—C7—N1	−3.9 (3)	C12—C13—C14—C15	−0.1 (4)
C3—C4—C5—C6	−1.3 (4)	C13—C14—C15—C10	−2.0 (3)
C7—C4—C5—C6	179.3 (2)	C13—C14—C15—N1	178.1 (2)
C3—C4—C7—C8	−1.6 (3)	C9—C16—C17—C18	178.9 (2)
C4—C5—C6—C1	−0.1 (4)	C21—C16—C17—C18	1.3 (3)
N1—C7—C8—C9	0.3 (3)	C9—C16—C21—C20	−178.7 (2)
C4—C7—C8—C9	178.6 (2)	C17—C16—C21—C20	−1.1 (3)
C7—C8—C9—C10	1.5 (3)	C16—C17—C18—C19	−0.1 (4)
C7—C8—C9—C16	−177.4 (2)	C17—C18—C19—C20	−1.5 (4)
C8—C9—C10—C15	−1.9 (3)	C18—C19—C20—C21	1.7 (4)
C16—C9—C10—C11	−5.3 (3)	C18—C19—C20—C22	−176.9 (2)
C8—C9—C16—C17	−53.6 (3)	C19—C20—C21—C16	−0.4 (3)
C8—C9—C16—C21	123.9 (2)	C22—C20—C21—C16	178.2 (2)
C16—C9—C10—C15	176.97 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···N1	0.93	2.43	2.764 (3)	101

Experimental details

Crystal data
Chemical formula	C₂₃H₁₈ClN
M_r	343.83
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	7.982 (3), 17.921 (6), 12.478 (4)
β (°)	92.581 (6)
V (Å³)	1783.1 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.23 × 0.22 × 0.22

Data collection
Diffractometer	Oxford Diffraction Xcalibur CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	16998, 3392, 2508
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.610

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.168, 1.04
No. of reflections	3392
No. of parameters	228
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.45

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2006).

Acknowledgements

SMK thanks the UGC–BRS and the University of Mysore for the award of a fellowship.

References

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