1-(4-Chloro­phen­yl)-2-[(3-phenyl­isoquinolin-1-yl)sulfan­yl]ethanone

Manivel, P.; Hathwar, V.R.; Nithya, P.; Subashini, R.; Nawaz Khan, F.

doi:10.1107/S1600536809000257

organic compounds

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Volume 65| Part 2| February 2009| Page o254

doi:10.1107/S1600536809000257

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1-(4-Chlorophenyl)-2-[(3-phenylisoquinolin-1-yl)sulfanyl]ethanone

P. Manivel,^a Venkatesha R. Hathwar,^b P. Nithya,^a R. Subashini ^a and F. Nawaz Khan ^a ^*

^aChemistry Division, School of Science and Humanities, VIT University, Vellore 632 014, Tamil Nadu, India, and ^bSolid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore 560 012, Karnataka, India
^*Correspondence e-mail: nawaz_f@yahoo.co.in

(Received 27 December 2008; accepted 5 January 2009; online 8 January 2009)

The title compound, C₂₃H₁₆ClNOS, exhibits dihedral angles of 11.73 (1) and 66.07 (1)°, respectively, between the mean plane of the isoquinoline system and the attached phenyl ring, and between the isoquinoline system and the chlorophenyl ring. The dihedral angle between the phenyl and chlorophenyl rings is 54.66 (1)°.

Related literature

For general background, see: Cremlyn et al. (1996 ); Carreno (1995 ); Kondo et al. (2000 ); Mosberg & Omnaas (1985 ); McReynolds et al. (2004 ). For related crystal structures, see: Hathwar et al. (2008 ); Manivel et al. (2009 ).

Experimental

Crystal data

C₂₃H₁₆ClNOS
M_r = 389.89
Orthorhombic, P b c a
a = 9.5874 (14) Å
b = 17.888 (3) Å
c = 22.025 (3) Å
V = 3777.3 (10) Å³
Z = 8
Mo Kα radiation
μ = 0.33 mm⁻¹
T = 290 (2) K
0.26 × 0.20 × 0.14 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.901, T_max = 0.956
25674 measured reflections
3332 independent reflections
1915 reflections with I > 2σ(I)
R_int = 0.116

Refinement

R[F² > 2σ(F²)] = 0.071
wR(F²) = 0.125
S = 1.04
3332 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: SMART (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); 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 ) and CAMERON (Watkin et al., 1993 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809000257/ng2532sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809000257/ng2532Isup2.hkl

checkCIF report

Comment top

Organic thioethers are useful synthetic intermediates, key reagents in organic synthesis, bio-organic, medicinal, and heterocyclic chemistry (Cremlyn, 1996 and McReynolds et al., 2004). They are also useful as heteroatomic functional groups in organic synthesis, for example, chiral sulphoxides can be generated by the oxidation of thioethers which are useful as auxiliaries in asymmetric syntheses (Carreno, 1995). Many syntheses have been reported for the preparation of thioethers in literature (Kondo et al., 2000) whereas commonly used method is the alkylation of thiols (Mosberg et al., 1985 and references there in).

The compound (I) forms the dihedral angles of 11.73 (1)° and 66.07 (1)° between mean plane of isoquinoline moiety and phenyl ring and mean plane of isoquinoline moiety and chlorophenyl ring respectively. The crystal packing is stabilized by C—H···O inter molecular Hydrogen bonds (Figure 2).

Related literature top

For general background, see: Cremlyn et al. (1996); Carreno (1995); Kondo et al. (2000); Mosberg & Omnaas (1985); McReynolds et al. (2004). For related crystal structures, see: Hathwar et al. (2008); Manivel et al. (2009).

Experimental top

3-Phenylisoquinoline-1-thiol and 2-bromo-1-(4-chlorophenyl)ethanone were mixed in the ratio 1:1.05 equivalents with ethanol in a round bottom flask. Then it was heated under nitrogen atmosphere on an oil bath at 323 K. After 2 h, the products were filtered and dissolved in chloroform. Further, it was washed with water, dried and concentrated. The single-crystal for X-ray structue anlaysis was obtained from ether solution by slow evaporation.

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. ORTEP diagram of the asymmetric unit of (I) with 50% probability displacement ellipsoids.
	Fig. 2. The crystal packing diagram of (I).The dotted lines indicate intermolecular C—H···O hydrogen bonds. All H atoms have been omitted for clarity.

1-(4-Chlorophenyl)-2-[(3-phenylisoquinolin-1-yl)sulfanyl]ethanone top

Crystal data top

C₂₃H₁₆ClNOS	F(000) = 1616
M_r = 389.89	D_x = 1.371 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 871 reflections
a = 9.5874 (14) Å	θ = 1.9–25.0°
b = 17.888 (3) Å	µ = 0.33 mm⁻¹
c = 22.025 (3) Å	T = 290 K
V = 3777.3 (10) Å³	Rod, colourless
Z = 8	0.26 × 0.20 × 0.14 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3332 independent reflections
Radiation source: fine-focus sealed tube	1915 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.116
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
T_min = 0.901, T_max = 0.956	k = −21→21
25674 measured reflections	l = −24→26

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)] = 0.071	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.125	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0308P)² + 0.7191P] where P = (F_o² + 2F_c²)/3
3332 reflections	(Δ/σ)_max < 0.001
244 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₃H₁₆ClNOS	V = 3777.3 (10) Å³
M_r = 389.89	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 9.5874 (14) Å	µ = 0.33 mm⁻¹
b = 17.888 (3) Å	T = 290 K
c = 22.025 (3) Å	0.26 × 0.20 × 0.14 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3332 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1915 reflections with I > 2σ(I)
T_min = 0.901, T_max = 0.956	R_int = 0.116
25674 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.071	0 restraints
wR(F²) = 0.125	H-atom parameters constrained
S = 1.04	Δρ_max = 0.23 e Å⁻³
3332 reflections	Δρ_min = −0.23 e Å⁻³
244 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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
Cl1	−0.16890 (17)	0.07371 (9)	0.25163 (6)	0.1375 (6)
S1	−0.09127 (10)	0.34062 (5)	−0.06818 (5)	0.0545 (3)
O1	0.0295 (2)	0.19469 (13)	−0.02148 (12)	0.0588 (7)
N1	0.0851 (3)	0.36685 (14)	0.02265 (13)	0.0406 (7)
C1	0.0416 (3)	0.39062 (18)	−0.03051 (16)	0.0401 (9)
C2	0.1941 (3)	0.40302 (18)	0.05067 (15)	0.0390 (9)
C3	0.2597 (4)	0.46147 (19)	0.02355 (16)	0.0460 (9)
H3	0.3348	0.4841	0.0430	0.055*
C4	0.2805 (4)	0.54850 (19)	−0.06405 (19)	0.0554 (10)
H4	0.3564	0.5724	−0.0463	0.067*
C5	0.2337 (5)	0.5720 (2)	−0.1189 (2)	0.0644 (12)
H5	0.2784	0.6111	−0.1387	0.077*
C6	0.1184 (5)	0.5375 (2)	−0.14581 (18)	0.0665 (12)
H6	0.0862	0.5543	−0.1832	0.080*
C7	0.0532 (4)	0.47981 (19)	−0.11778 (17)	0.0570 (11)
H7	−0.0237	0.4575	−0.1360	0.068*
C8	0.1007 (4)	0.45349 (17)	−0.06155 (16)	0.0410 (8)
C9	0.2160 (4)	0.48838 (17)	−0.03338 (16)	0.0428 (9)
C10	0.2362 (4)	0.3727 (2)	0.11049 (16)	0.0439 (9)
C11	0.3618 (4)	0.3927 (2)	0.13781 (17)	0.0656 (12)
H11	0.4201	0.4267	0.1184	0.079*
C12	0.4012 (5)	0.3632 (3)	0.19275 (19)	0.0801 (13)
H12	0.4854	0.3779	0.2100	0.096*
C13	0.3193 (5)	0.3129 (3)	0.22247 (19)	0.0778 (13)
H13	0.3463	0.2933	0.2598	0.093*
C14	0.1957 (5)	0.2919 (2)	0.19589 (19)	0.0748 (13)
H14	0.1390	0.2570	0.2152	0.090*
C15	0.1543 (4)	0.3218 (2)	0.14102 (17)	0.0594 (11)
H15	0.0694	0.3072	0.1243	0.071*
C16	−0.1538 (3)	0.28339 (18)	−0.00757 (16)	0.0486 (10)
H16A	−0.1685	0.3150	0.0276	0.058*
H16B	−0.2440	0.2634	−0.0193	0.058*
C17	−0.0618 (4)	0.21887 (18)	0.01117 (18)	0.0454 (10)
C18	−0.0910 (4)	0.18457 (17)	0.07171 (18)	0.0470 (9)
C19	−0.2116 (4)	0.1996 (2)	0.10416 (18)	0.0529 (10)
H19	−0.2767	0.2330	0.0885	0.064*
C20	−0.2360 (4)	0.1656 (3)	0.15937 (19)	0.0693 (12)
H20	−0.3179	0.1754	0.1806	0.083*
C21	−0.1389 (6)	0.1174 (3)	0.18275 (19)	0.0769 (13)
C22	−0.0177 (5)	0.1022 (2)	0.1514 (2)	0.0762 (13)
H22	0.0480	0.0695	0.1675	0.091*
C23	0.0055 (4)	0.1354 (2)	0.0962 (2)	0.0630 (11)
H23	0.0869	0.1249	0.0750	0.076*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1541 (14)	0.1891 (16)	0.0694 (9)	−0.0056 (13)	−0.0200 (9)	0.0362 (10)
S1	0.0462 (6)	0.0542 (5)	0.0632 (7)	−0.0085 (5)	−0.0116 (6)	−0.0032 (5)
O1	0.0391 (15)	0.0504 (15)	0.087 (2)	0.0030 (12)	0.0112 (15)	−0.0136 (14)
N1	0.0357 (17)	0.0379 (15)	0.0481 (19)	−0.0030 (14)	0.0007 (16)	−0.0072 (14)
C1	0.032 (2)	0.038 (2)	0.050 (2)	0.0031 (16)	0.0014 (18)	−0.0074 (18)
C2	0.036 (2)	0.037 (2)	0.045 (2)	0.0020 (17)	0.0029 (17)	−0.0125 (17)
C3	0.044 (2)	0.040 (2)	0.054 (2)	−0.0063 (17)	−0.005 (2)	−0.0126 (19)
C4	0.055 (3)	0.040 (2)	0.071 (3)	−0.0047 (19)	0.010 (2)	−0.005 (2)
C5	0.074 (3)	0.043 (2)	0.076 (3)	−0.001 (2)	0.017 (3)	0.006 (2)
C6	0.084 (3)	0.058 (3)	0.058 (3)	0.005 (2)	0.003 (3)	0.011 (2)
C7	0.060 (3)	0.048 (2)	0.063 (3)	0.000 (2)	−0.004 (2)	0.003 (2)
C8	0.042 (2)	0.0353 (18)	0.046 (2)	0.0077 (17)	0.0068 (19)	−0.0053 (18)
C9	0.043 (2)	0.0303 (19)	0.055 (2)	−0.0010 (17)	0.007 (2)	−0.0096 (18)
C10	0.040 (2)	0.047 (2)	0.045 (2)	−0.0009 (18)	0.001 (2)	−0.0121 (19)
C11	0.057 (3)	0.087 (3)	0.054 (3)	−0.015 (2)	−0.002 (2)	0.004 (2)
C12	0.064 (3)	0.119 (4)	0.057 (3)	−0.018 (3)	−0.013 (3)	0.003 (3)
C13	0.082 (4)	0.101 (4)	0.050 (3)	−0.005 (3)	−0.010 (3)	0.006 (3)
C14	0.084 (3)	0.078 (3)	0.063 (3)	−0.016 (3)	−0.009 (3)	0.019 (3)
C15	0.060 (3)	0.059 (3)	0.058 (3)	−0.009 (2)	−0.011 (2)	0.005 (2)
C16	0.033 (2)	0.044 (2)	0.068 (3)	−0.0058 (17)	−0.0008 (19)	−0.0072 (19)
C17	0.031 (2)	0.0346 (19)	0.071 (3)	−0.0067 (17)	−0.005 (2)	−0.011 (2)
C18	0.039 (2)	0.0350 (18)	0.067 (3)	−0.0037 (18)	−0.005 (2)	−0.012 (2)
C19	0.047 (3)	0.053 (2)	0.058 (3)	−0.002 (2)	−0.008 (2)	−0.008 (2)
C20	0.059 (3)	0.091 (3)	0.058 (3)	−0.009 (3)	−0.006 (3)	−0.013 (3)
C21	0.084 (4)	0.090 (3)	0.057 (3)	−0.012 (3)	−0.019 (3)	−0.003 (3)
C22	0.077 (4)	0.062 (3)	0.090 (4)	0.004 (3)	−0.030 (3)	0.007 (3)
C23	0.050 (3)	0.050 (2)	0.089 (3)	0.002 (2)	−0.008 (2)	−0.001 (2)

Geometric parameters (Å, º) top

Cl1—C21	1.731 (4)	C11—C12	1.373 (5)
S1—C1	1.764 (3)	C11—H11	0.9300
S1—C16	1.786 (3)	C12—C13	1.362 (5)
O1—C17	1.212 (4)	C12—H12	0.9300
N1—C1	1.314 (4)	C13—C14	1.374 (5)
N1—C2	1.375 (4)	C13—H13	0.9300
C1—C8	1.433 (4)	C14—C15	1.379 (5)
C2—C3	1.359 (4)	C14—H14	0.9300
C2—C10	1.481 (4)	C15—H15	0.9300
C3—C9	1.407 (4)	C16—C17	1.510 (4)
C3—H3	0.9300	C16—H16A	0.9700
C4—C5	1.355 (5)	C16—H16B	0.9700
C4—C9	1.412 (4)	C17—C18	1.494 (5)
C4—H4	0.9300	C18—C23	1.385 (5)
C5—C6	1.398 (5)	C18—C19	1.385 (5)
C5—H5	0.9300	C19—C20	1.380 (5)
C6—C7	1.355 (5)	C19—H19	0.9300
C6—H6	0.9300	C20—C21	1.369 (6)
C7—C8	1.401 (4)	C20—H20	0.9300
C7—H7	0.9300	C21—C22	1.380 (6)
C8—C9	1.413 (4)	C22—C23	1.371 (5)
C10—C15	1.378 (4)	C22—H22	0.9300
C10—C11	1.392 (5)	C23—H23	0.9300

C1—S1—C16	100.46 (17)	C11—C12—H12	119.4
C1—N1—C2	119.3 (3)	C12—C13—C14	118.2 (4)
N1—C1—C8	123.6 (3)	C12—C13—H13	120.9
N1—C1—S1	119.0 (3)	C14—C13—H13	120.9
C8—C1—S1	117.3 (3)	C13—C14—C15	121.0 (4)
C3—C2—N1	121.1 (3)	C13—C14—H14	119.5
C3—C2—C10	123.1 (3)	C15—C14—H14	119.5
N1—C2—C10	115.8 (3)	C10—C15—C14	121.3 (4)
C2—C3—C9	121.2 (3)	C10—C15—H15	119.4
C2—C3—H3	119.4	C14—C15—H15	119.4
C9—C3—H3	119.4	C17—C16—S1	116.5 (2)
C5—C4—C9	121.1 (4)	C17—C16—H16A	108.2
C5—C4—H4	119.4	S1—C16—H16A	108.2
C9—C4—H4	119.4	C17—C16—H16B	108.2
C4—C5—C6	120.3 (4)	S1—C16—H16B	108.2
C4—C5—H5	119.9	H16A—C16—H16B	107.3
C6—C5—H5	119.9	O1—C17—C18	121.2 (3)
C7—C6—C5	120.5 (4)	O1—C17—C16	122.2 (3)
C7—C6—H6	119.8	C18—C17—C16	116.6 (3)
C5—C6—H6	119.8	C23—C18—C19	118.6 (4)
C6—C7—C8	120.6 (4)	C23—C18—C17	118.9 (4)
C6—C7—H7	119.7	C19—C18—C17	122.5 (3)
C8—C7—H7	119.7	C20—C19—C18	120.7 (4)
C7—C8—C9	119.6 (3)	C20—C19—H19	119.6
C7—C8—C1	123.8 (3)	C18—C19—H19	119.6
C9—C8—C1	116.5 (3)	C21—C20—C19	119.6 (4)
C3—C9—C4	123.8 (3)	C21—C20—H20	120.2
C3—C9—C8	118.2 (3)	C19—C20—H20	120.2
C4—C9—C8	118.0 (3)	C20—C21—C22	120.6 (4)
C15—C10—C11	116.9 (4)	C20—C21—Cl1	120.1 (4)
C15—C10—C2	121.4 (3)	C22—C21—Cl1	119.3 (4)
C11—C10—C2	121.8 (3)	C23—C22—C21	119.7 (4)
C12—C11—C10	121.3 (4)	C23—C22—H22	120.2
C12—C11—H11	119.3	C21—C22—H22	120.2
C10—C11—H11	119.3	C22—C23—C18	120.8 (4)
C13—C12—C11	121.3 (4)	C22—C23—H23	119.6
C13—C12—H12	119.4	C18—C23—H23	119.6

C2—N1—C1—C8	−0.6 (4)	C3—C2—C10—C11	−12.3 (5)
C2—N1—C1—S1	176.3 (2)	N1—C2—C10—C11	165.9 (3)
C16—S1—C1—N1	14.4 (3)	C15—C10—C11—C12	−0.4 (6)
C16—S1—C1—C8	−168.5 (2)	C2—C10—C11—C12	−178.8 (4)
C1—N1—C2—C3	−1.8 (4)	C10—C11—C12—C13	0.4 (7)
C1—N1—C2—C10	179.9 (3)	C11—C12—C13—C14	0.3 (7)
N1—C2—C3—C9	1.8 (5)	C12—C13—C14—C15	−1.0 (7)
C10—C2—C3—C9	180.0 (3)	C11—C10—C15—C14	−0.3 (6)
C9—C4—C5—C6	1.0 (6)	C2—C10—C15—C14	178.1 (3)
C4—C5—C6—C7	−0.8 (6)	C13—C14—C15—C10	1.0 (6)
C5—C6—C7—C8	−0.3 (6)	C1—S1—C16—C17	−73.9 (3)
C6—C7—C8—C9	1.2 (5)	S1—C16—C17—O1	−18.5 (4)
C6—C7—C8—C1	−176.9 (3)	S1—C16—C17—C18	163.1 (2)
N1—C1—C8—C7	−178.9 (3)	O1—C17—C18—C23	13.8 (5)
S1—C1—C8—C7	4.2 (4)	C16—C17—C18—C23	−167.7 (3)
N1—C1—C8—C9	2.9 (5)	O1—C17—C18—C19	−165.7 (3)
S1—C1—C8—C9	−174.0 (2)	C16—C17—C18—C19	12.8 (4)
C2—C3—C9—C4	−179.5 (3)	C23—C18—C19—C20	−0.8 (5)
C2—C3—C9—C8	0.7 (5)	C17—C18—C19—C20	178.7 (3)
C5—C4—C9—C3	−180.0 (3)	C18—C19—C20—C21	1.0 (6)
C5—C4—C9—C8	−0.2 (5)	C19—C20—C21—C22	−0.5 (6)
C7—C8—C9—C3	178.9 (3)	C19—C20—C21—Cl1	−179.4 (3)
C1—C8—C9—C3	−2.8 (4)	C20—C21—C22—C23	−0.2 (6)
C7—C8—C9—C4	−0.9 (4)	Cl1—C21—C22—C23	178.7 (3)
C1—C8—C9—C4	177.3 (3)	C21—C22—C23—C18	0.4 (6)
C3—C2—C10—C15	169.4 (3)	C19—C18—C23—C22	0.1 (5)
N1—C2—C10—C15	−12.4 (4)	C17—C18—C23—C22	−179.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1ⁱ	0.93	2.51	3.322 (4)	147
C16—H16B···O1ⁱⁱ	0.97	2.47	3.128 (4)	125

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

Experimental details

Crystal data
Chemical formula	C₂₃H₁₆ClNOS
M_r	389.89
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	290
a, b, c (Å)	9.5874 (14), 17.888 (3), 22.025 (3)
V (Å³)	3777.3 (10)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.33
Crystal size (mm)	0.26 × 0.20 × 0.14

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.901, 0.956
No. of measured, independent and observed [I > 2σ(I)] reflections	25674, 3332, 1915
R_int	0.116
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.071, 0.125, 1.04
No. of reflections	3332
No. of parameters	244
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.23

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993).

Acknowledgements

We thank the Department of Science and Technology, India, for use of the CCD facility set up under the IRHPA–DST program at IISc. We thank Prof T. N. Guru Row, IISc, Bangalore, for useful crystallographic discussions. FNK thanks the DST for Fast Track Proposal funding.

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