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

Manivel, P.; Hathwar, V.R.; Maiyalagan, T.; Arslan, N.B.; Nawaz Khan, F.

doi:10.1107/S1600536809001573

organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page o334

doi:10.1107/S1600536809001573

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

P. Manivel,^a Venkatesha R. Hathwar,^b T. Maiyalagan,^a N. Burcu Arslan ^c and F. Nawaz Khan ^a ^*

^aChemistry Division, School of Science and Humanities, VIT University, Vellore 632 014, Tamil Nadu, India, ^bSolid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore 560 012, Karnataka, India, and ^cOndokuz Mayıs University, Arts and Sciences Faculty, Department of Physics, 55139-Samsun, Turkey
^*Correspondence e-mail: nawaz_f@yahoo.co.in

(Received 5 January 2009; accepted 13 January 2009; online 17 January 2009)

In the title compound, C₂₃H₁₅ClFNOS, the isoquinoline system and the 4-chloro-3-fluorophenyl ring are aligned at 80.4 (1)°. The dihedral angle between the isoquinoline system and the pendant (unsubstituted) phenyl ring is 19.91 (1)°.

Related literature

For related structures, see: Hathwar et al. (2008 ); Manivel et al. (2009a ,b ).

Experimental

Crystal data

C₂₃H₁₅ClFNOS
M_r = 407.87
Orthorhombic, P b c a
a = 16.9008 (11) Å
b = 9.8036 (7) Å
c = 23.3226 (16) Å
V = 3864.3 (5) Å³
Z = 8
Mo Kα radiation
μ = 0.33 mm⁻¹
T = 290 (2) K
0.24 × 0.18 × 0.11 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.925, T_max = 0.965
27428 measured reflections
3595 independent reflections
2424 reflections with I > 2σ(I)
R_int = 0.063

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.128
S = 1.04
3595 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.19 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: PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809001573/ng2534sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809001573/ng2534Isup2.hkl

checkCIF report

Comment top

In compound (I), the S atom also located in the plane. The F atom deviates by 0.014 A from mean plane of phenyl ring containing F and Cl atoms. In this ring F– C and Cl—C bond distances are 1.348 (4) A, 1.727 (3) A, respectively. The orientation of isoquinoline ring system with respect to the another phenyl ring is given by the torsion angles for N1—C2—C10—C15 and C3—C2—C10—C11 are respectively -160.1 (2)°, -163.1 (3)° similarly for C16—S1—C1—N1 and C16—S1—C1—C8 are respectively -0.8 (2)° and 179.56 (19)° (Table 1).

Related literature top

For related structures, see: Hathwar et al. (2008); Manivel et al. (2009a,b).

Experimental top

3-Phenylisoquinoline-1-thiol and 2-bromo-1-(3-fluoro-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: PLATON (Spek, 2003).

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-Chloro-3-fluorophenyl)-2-[(3-phenylisoquinolin-1-yl)sulfanyl]ethanone top

Crystal data top

C₂₃H₁₅ClFNOS	F(000) = 1680
M_r = 407.87	D_x = 1.402 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3595 reflections
a = 16.9008 (11) Å	θ = 1.8–25.5°
b = 9.8036 (7) Å	µ = 0.33 mm⁻¹
c = 23.3226 (16) Å	T = 290 K
V = 3864.3 (5) Å³	Block, colourless
Z = 8	0.24 × 0.18 × 0.11 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3595 independent reflections
Radiation source: fine-focus sealed tube	2424 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.063
ϕ and ω scans	θ_max = 25.5°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→20
T_min = 0.925, T_max = 0.965	k = −11→11
27428 measured reflections	l = −28→28

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.128	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0566P)² + 1.1665P] where P = (F_o² + 2F_c²)/3
3595 reflections	(Δ/σ)_max = 0.001
253 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₂₃H₁₅ClFNOS	V = 3864.3 (5) Å³
M_r = 407.87	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 16.9008 (11) Å	µ = 0.33 mm⁻¹
b = 9.8036 (7) Å	T = 290 K
c = 23.3226 (16) Å	0.24 × 0.18 × 0.11 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3595 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2424 reflections with I > 2σ(I)
T_min = 0.925, T_max = 0.965	R_int = 0.063
27428 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.128	H-atom parameters constrained
S = 1.04	Δρ_max = 0.32 e Å⁻³
3595 reflections	Δρ_min = −0.19 e Å⁻³
253 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.07142 (12)	0.8183 (2)	0.28005 (9)	0.0633 (6)
F1	0.09785 (13)	0.8393 (2)	0.06905 (9)	0.1057 (7)
S1	0.03138 (4)	0.61721 (7)	0.37120 (3)	0.0495 (2)
Cl1	−0.02952 (8)	0.70329 (14)	0.00961 (4)	0.1221 (5)
N1	0.12270 (12)	0.4853 (2)	0.29715 (9)	0.0399 (5)
C1	0.11497 (15)	0.5201 (2)	0.35092 (11)	0.0393 (6)
C2	0.18572 (14)	0.4054 (2)	0.28104 (11)	0.0405 (6)
C3	0.24276 (16)	0.3684 (3)	0.31906 (11)	0.0474 (7)
H3	0.2861	0.3180	0.3066	0.057*
C4	0.29398 (18)	0.3701 (3)	0.41884 (13)	0.0593 (8)
H4	0.3384	0.3205	0.4079	0.071*
C5	0.2845 (2)	0.4076 (3)	0.47468 (14)	0.0688 (9)
H5	0.3225	0.3827	0.5016	0.083*
C6	0.2188 (2)	0.4828 (3)	0.49197 (13)	0.0643 (9)
H6	0.2135	0.5085	0.5302	0.077*
C7	0.16226 (18)	0.5189 (3)	0.45299 (12)	0.0538 (7)
H7	0.1180	0.5676	0.4650	0.065*
C8	0.17027 (16)	0.4832 (2)	0.39492 (11)	0.0422 (6)
C9	0.23657 (16)	0.4063 (3)	0.37753 (11)	0.0451 (6)
C10	0.18550 (14)	0.3638 (2)	0.21970 (11)	0.0419 (6)
C11	0.13897 (17)	0.4309 (3)	0.18011 (12)	0.0515 (7)
H11	0.1085	0.5046	0.1921	0.062*
C12	0.13641 (19)	0.3920 (3)	0.12340 (12)	0.0597 (8)
H12	0.1046	0.4392	0.0976	0.072*
C13	0.18110 (19)	0.2828 (3)	0.10499 (13)	0.0641 (9)
H13	0.1805	0.2569	0.0666	0.077*
C14	0.22641 (19)	0.2130 (4)	0.14375 (14)	0.0715 (10)
H14	0.2556	0.1379	0.1317	0.086*
C15	0.22938 (17)	0.2524 (3)	0.20044 (13)	0.0598 (8)
H15	0.2609	0.2042	0.2261	0.072*
C16	−0.01524 (15)	0.6351 (3)	0.30300 (11)	0.0439 (6)
H16A	−0.0177	0.5461	0.2849	0.053*
H16B	−0.0692	0.6659	0.3089	0.053*
C17	0.02538 (15)	0.7327 (2)	0.26264 (12)	0.0426 (6)
C18	0.00791 (15)	0.7226 (2)	0.20013 (12)	0.0422 (6)
C19	0.05916 (17)	0.7874 (3)	0.16253 (13)	0.0520 (7)
H19	0.1020	0.8366	0.1766	0.062*
C20	0.0465 (2)	0.7788 (3)	0.10523 (15)	0.0647 (9)
C21	−0.0164 (2)	0.7098 (4)	0.08298 (14)	0.0679 (9)
C22	−0.0680 (2)	0.6464 (3)	0.11953 (15)	0.0714 (9)
H22	−0.1116	0.6000	0.1049	0.086*
C23	−0.05585 (18)	0.6510 (3)	0.17826 (13)	0.0572 (8)
H23	−0.0904	0.6062	0.2029	0.069*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0674 (14)	0.0532 (12)	0.0694 (14)	−0.0142 (11)	−0.0162 (11)	−0.0004 (10)
F1	0.1066 (17)	0.1363 (19)	0.0742 (14)	−0.0033 (15)	0.0267 (12)	0.0272 (13)
S1	0.0554 (5)	0.0517 (4)	0.0412 (4)	0.0142 (3)	0.0010 (3)	−0.0073 (3)
Cl1	0.1660 (12)	0.1504 (11)	0.0500 (6)	0.0166 (9)	−0.0195 (6)	0.0006 (6)
N1	0.0408 (13)	0.0394 (12)	0.0396 (12)	0.0018 (10)	0.0016 (10)	−0.0030 (9)
C1	0.0454 (16)	0.0322 (13)	0.0404 (15)	−0.0012 (11)	0.0021 (12)	−0.0003 (11)
C2	0.0372 (15)	0.0380 (14)	0.0462 (15)	−0.0010 (11)	0.0047 (12)	−0.0020 (12)
C3	0.0381 (15)	0.0473 (15)	0.0570 (17)	0.0062 (12)	0.0002 (14)	−0.0042 (14)
C4	0.0579 (19)	0.0559 (18)	0.064 (2)	0.0096 (15)	−0.0138 (16)	0.0034 (16)
C5	0.081 (2)	0.068 (2)	0.058 (2)	0.0080 (19)	−0.0261 (18)	0.0111 (17)
C6	0.090 (2)	0.0590 (19)	0.0443 (17)	0.0110 (18)	−0.0115 (17)	0.0026 (14)
C7	0.070 (2)	0.0462 (16)	0.0448 (17)	0.0078 (15)	−0.0052 (14)	0.0015 (13)
C8	0.0501 (16)	0.0346 (13)	0.0419 (15)	−0.0011 (12)	−0.0037 (12)	0.0025 (11)
C9	0.0481 (16)	0.0368 (14)	0.0505 (16)	−0.0013 (12)	−0.0068 (13)	0.0021 (12)
C10	0.0368 (15)	0.0425 (14)	0.0464 (16)	−0.0034 (12)	0.0067 (12)	−0.0055 (12)
C11	0.0665 (19)	0.0400 (15)	0.0479 (17)	0.0057 (14)	0.0020 (15)	−0.0024 (13)
C12	0.077 (2)	0.0564 (17)	0.0457 (17)	0.0053 (16)	−0.0019 (15)	0.0004 (14)
C13	0.065 (2)	0.081 (2)	0.0468 (18)	0.0032 (18)	0.0075 (16)	−0.0157 (16)
C14	0.058 (2)	0.091 (3)	0.065 (2)	0.0256 (19)	0.0001 (17)	−0.0299 (19)
C15	0.0466 (18)	0.074 (2)	0.0585 (19)	0.0217 (16)	−0.0017 (14)	−0.0164 (16)
C16	0.0429 (16)	0.0415 (15)	0.0472 (16)	0.0076 (12)	0.0010 (12)	−0.0031 (12)
C17	0.0383 (15)	0.0353 (14)	0.0543 (17)	0.0055 (12)	−0.0039 (13)	−0.0023 (12)
C18	0.0410 (15)	0.0341 (13)	0.0514 (17)	0.0041 (12)	−0.0020 (13)	0.0016 (12)
C19	0.0485 (17)	0.0474 (17)	0.060 (2)	0.0057 (13)	0.0024 (14)	0.0034 (14)
C20	0.069 (2)	0.069 (2)	0.056 (2)	0.0130 (18)	0.0129 (18)	0.0134 (16)
C21	0.087 (3)	0.072 (2)	0.0453 (18)	0.018 (2)	−0.0032 (18)	0.0037 (16)
C22	0.081 (2)	0.070 (2)	0.064 (2)	−0.0032 (18)	−0.0258 (19)	−0.0049 (17)
C23	0.0612 (19)	0.0512 (17)	0.059 (2)	−0.0033 (14)	−0.0071 (16)	0.0041 (14)

Geometric parameters (Å, º) top

O1—C17	1.215 (3)	C10—C15	1.395 (3)
F1—C20	1.348 (4)	C11—C12	1.377 (4)
S1—C1	1.768 (3)	C11—H11	0.9300
S1—C16	1.784 (3)	C12—C13	1.378 (4)
Cl1—C21	1.727 (3)	C12—H12	0.9300
N1—C1	1.306 (3)	C13—C14	1.368 (4)
N1—C2	1.375 (3)	C13—H13	0.9300
C1—C8	1.434 (3)	C14—C15	1.378 (4)
C2—C3	1.359 (3)	C14—H14	0.9300
C2—C10	1.487 (3)	C15—H15	0.9300
C3—C9	1.417 (3)	C16—C17	1.508 (4)
C3—H3	0.9300	C16—H16A	0.9700
C4—C5	1.363 (4)	C16—H16B	0.9700
C4—C9	1.413 (4)	C17—C18	1.491 (4)
C4—H4	0.9300	C18—C23	1.383 (4)
C5—C6	1.392 (4)	C18—C19	1.387 (4)
C5—H5	0.9300	C19—C20	1.356 (4)
C6—C7	1.366 (4)	C19—H19	0.9300
C6—H6	0.9300	C20—C21	1.363 (5)
C7—C8	1.405 (4)	C21—C22	1.369 (5)
C7—H7	0.9300	C22—C23	1.386 (4)
C8—C9	1.410 (3)	C22—H22	0.9300
C10—C11	1.380 (4)	C23—H23	0.9300

C1—S1—C16	99.63 (12)	C13—C12—H12	120.1
C1—N1—C2	119.3 (2)	C14—C13—C12	119.3 (3)
N1—C1—C8	123.8 (2)	C14—C13—H13	120.3
N1—C1—S1	118.51 (19)	C12—C13—H13	120.3
C8—C1—S1	117.71 (19)	C13—C14—C15	120.9 (3)
C3—C2—N1	121.5 (2)	C13—C14—H14	119.5
C3—C2—C10	123.8 (2)	C15—C14—H14	119.5
N1—C2—C10	114.7 (2)	C14—C15—C10	120.6 (3)
C2—C3—C9	120.4 (2)	C14—C15—H15	119.7
C2—C3—H3	119.8	C10—C15—H15	119.7
C9—C3—H3	119.8	C17—C16—S1	114.70 (19)
C5—C4—C9	120.2 (3)	C17—C16—H16A	108.6
C5—C4—H4	119.9	S1—C16—H16A	108.6
C9—C4—H4	119.9	C17—C16—H16B	108.6
C4—C5—C6	120.9 (3)	S1—C16—H16B	108.6
C4—C5—H5	119.6	H16A—C16—H16B	107.6
C6—C5—H5	119.6	O1—C17—C18	120.0 (2)
C7—C6—C5	120.2 (3)	O1—C17—C16	121.5 (3)
C7—C6—H6	119.9	C18—C17—C16	118.6 (2)
C5—C6—H6	119.9	C23—C18—C19	119.1 (3)
C6—C7—C8	120.6 (3)	C23—C18—C17	123.3 (3)
C6—C7—H7	119.7	C19—C18—C17	117.7 (2)
C8—C7—H7	119.7	C20—C19—C18	119.7 (3)
C7—C8—C9	119.2 (2)	C20—C19—H19	120.1
C7—C8—C1	124.3 (2)	C18—C19—H19	120.1
C9—C8—C1	116.5 (2)	F1—C20—C19	119.2 (3)
C8—C9—C4	118.9 (3)	F1—C20—C21	118.8 (3)
C8—C9—C3	118.4 (2)	C19—C20—C21	122.0 (3)
C4—C9—C3	122.7 (3)	C20—C21—C22	119.0 (3)
C11—C10—C15	117.4 (2)	C20—C21—Cl1	119.7 (3)
C11—C10—C2	120.9 (2)	C22—C21—Cl1	121.2 (3)
C15—C10—C2	121.6 (2)	C21—C22—C23	120.4 (3)
C12—C11—C10	121.9 (3)	C21—C22—H22	119.8
C12—C11—H11	119.0	C23—C22—H22	119.8
C10—C11—H11	119.0	C18—C23—C22	119.8 (3)
C11—C12—C13	119.8 (3)	C18—C23—H23	120.1
C11—C12—H12	120.1	C22—C23—H23	120.1

C2—N1—C1—C8	2.0 (4)	C15—C10—C11—C12	−1.1 (4)
C2—N1—C1—S1	−177.53 (17)	C2—C10—C11—C12	−178.4 (3)
C16—S1—C1—N1	−0.8 (2)	C10—C11—C12—C13	0.2 (4)
C16—S1—C1—C8	179.56 (19)	C11—C12—C13—C14	1.2 (5)
C1—N1—C2—C3	−4.0 (4)	C12—C13—C14—C15	−1.6 (5)
C1—N1—C2—C10	175.8 (2)	C13—C14—C15—C10	0.6 (5)
N1—C2—C3—C9	3.1 (4)	C11—C10—C15—C14	0.7 (4)
C10—C2—C3—C9	−176.7 (2)	C2—C10—C15—C14	178.0 (3)
C9—C4—C5—C6	−0.5 (5)	C1—S1—C16—C17	−73.20 (19)
C4—C5—C6—C7	0.7 (5)	S1—C16—C17—O1	−19.3 (3)
C5—C6—C7—C8	−1.2 (4)	S1—C16—C17—C18	160.73 (18)
C6—C7—C8—C9	1.6 (4)	O1—C17—C18—C23	−164.7 (3)
C6—C7—C8—C1	−178.2 (3)	C16—C17—C18—C23	15.2 (4)
N1—C1—C8—C7	−179.4 (2)	O1—C17—C18—C19	16.0 (4)
S1—C1—C8—C7	0.1 (3)	C16—C17—C18—C19	−164.1 (2)
N1—C1—C8—C9	0.7 (4)	C23—C18—C19—C20	−0.6 (4)
S1—C1—C8—C9	−179.71 (18)	C17—C18—C19—C20	178.7 (2)
C7—C8—C9—C4	−1.5 (4)	C18—C19—C20—F1	−178.3 (2)
C1—C8—C9—C4	178.4 (2)	C18—C19—C20—C21	1.2 (5)
C7—C8—C9—C3	178.5 (2)	F1—C20—C21—C22	179.0 (3)
C1—C8—C9—C3	−1.6 (3)	C19—C20—C21—C22	−0.5 (5)
C5—C4—C9—C8	0.9 (4)	F1—C20—C21—Cl1	−0.8 (4)
C5—C4—C9—C3	−179.1 (3)	C19—C20—C21—Cl1	179.7 (2)
C2—C3—C9—C8	−0.2 (4)	C20—C21—C22—C23	−0.8 (5)
C2—C3—C9—C4	179.8 (3)	Cl1—C21—C22—C23	179.0 (2)
C3—C2—C10—C11	−163.1 (3)	C19—C18—C23—C22	−0.7 (4)
N1—C2—C10—C11	17.1 (3)	C17—C18—C23—C22	−180.0 (3)
C3—C2—C10—C15	19.7 (4)	C21—C22—C23—C18	1.4 (5)
N1—C2—C10—C15	−160.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···S1	0.93	2.68	3.076 (3)	107
C11—H11···N1	0.93	2.47	2.795 (4)	101

Experimental details

Crystal data
Chemical formula	C₂₃H₁₅ClFNOS
M_r	407.87
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	290
a, b, c (Å)	16.9008 (11), 9.8036 (7), 23.3226 (16)
V (Å³)	3864.3 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.33
Crystal size (mm)	0.24 × 0.18 × 0.11

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.925, 0.965
No. of measured, independent and observed [I > 2σ(I)] reflections	27428, 3595, 2424
R_int	0.063
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.128, 1.04
No. of reflections	3595
No. of parameters	253
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.19

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia,1997) and CAMERON (Watkin et al., 1993), PLATON (Spek, 2003).

Acknowledgements

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

References

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