5-Phenyl-3-(2-thien­yl)-1,2,4-triazolo[3,4-a]isoquinoline

Khan, F.N.; Manivel, P.; Prabakaran, K.; Hathwar, V.R.; Ng, S.W.

doi:10.1107/S1600536810003181

organic compounds

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ISSN: 2056-9890

Volume 66| Part 2| February 2010| Page o488

https://doi.org/10.1107/S1600536810003181

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5-Phenyl-3-(2-thienyl)-1,2,4-triazolo[3,4-a]isoquinoline

F. Nawaz Khan,^a P. Manivel,^a K. Prabakaran,^a Venkatesha R. Hathwar ^b and Seik Weng Ng ^c ^*

^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 ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 19 January 2010; accepted 25 January 2010; online 30 January 2010)

In the title molecule, C₂₀H₁₃N₃S, the triazoloisoquinoline ring system is approximately planar, with an r.m.s. deviation of 0.045 Å and a maximum deviation of 0.090 (2) Å from the mean plane for the triazole ring C atom which is bonded to the thiophene ring. The phenyl ring is twisted by 52.0 (1)° with respect to the mean plane of the triazoloisoquinoline ring system. The thiophene ring is rotationally disordered by approximately 180° over two sites, the ratio of refined occupancies being 0.73 (1):0.27 (1).

Related literature

For the synthesis and antihelmintic activity of triazolo compounds similar to the title compound, see: Nadkarni et al. (2001 ).

Experimental

Crystal data

C₂₀H₁₃N₃S
M_r = 327.39
Orthorhombic, P 2₁ 2₁ 2
a = 19.7715 (17) Å
b = 8.7735 (7) Å
c = 9.3027 (8) Å
V = 1613.7 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 293 K
0.32 × 0.30 × 0.24 mm

Data collection

Bruker SMART area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.937, T_max = 0.952
10809 measured reflections
3670 independent reflections
2414 reflections with I > 2σ(I)
R_int = 0.045

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.128
S = 1.03
3670 reflections
230 parameters
45 restraints
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.21 e Å⁻³
Absolute structure: Flack (1983 ), 1631 Friedel pairs
Flack parameter: 0.05 (13)

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: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810003181/lh2984sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810003181/lh2984Isup2.hkl

checkCIF report

Comment top

The molecular structure of the title compound is shown in Fig. 1.

Related literature top

For the synthesis and antihelmintic activity of triazolo compounds similar to the title compound, see: Nadkarni et al. (2001).

Experimental top

2-(3-Phenylisoquinolin-1-yl)hydrazine (1 mmol) was condensed with thienyl-2-carbaldehye (1.1 mmol) under refluxing conditions isopropanol (10 ml) solvent to give the corresponding 2-(3-phenylisoquinolin-1-yl)-1-(2-thienylmethylene)hydrazine in high yield. The compound was then oxidatively cyclized in nitrobenzene (10 ml) at 473 K. The product was recrystallized from dichlomethane to give block-shaped crystals.

Structure description top

The molecular structure of the title compound is shown in Fig. 1.

For the synthesis and antihelmintic activity of triazolo compounds similar to the title compound, see: Nadkarni et al. (2001).

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: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C₂₀H₁₃N₃S at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. The disorder is not shown.

5-Phenyl-3-(2-thienyl)-1,2,4-triazolo[3,4-a]isoquinoline top

Crystal data top

C₂₀H₁₃N₃S	F(000) = 680
M_r = 327.39	D_x = 1.348 Mg m⁻³
Orthorhombic, P2₁2₁2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2 2ab	Cell parameters from 1886 reflections
a = 19.7715 (17) Å	θ = 2.4–20.1°
b = 8.7735 (7) Å	µ = 0.21 mm⁻¹
c = 9.3027 (8) Å	T = 293 K
V = 1613.7 (2) Å³	Block, yellow
Z = 4	0.32 × 0.30 × 0.24 mm

Data collection top

Bruker SMART area-detector diffractometer	3670 independent reflections
Radiation source: fine-focus sealed tube	2414 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
φ and ω scans	θ_max = 27.5°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −25→25
T_min = 0.937, T_max = 0.952	k = −11→10
10809 measured reflections	l = −10→12

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.057	H-atom parameters constrained
wR(F²) = 0.128	w = 1/[σ²(F_o²) + (0.0577P)²] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
3670 reflections	Δρ_max = 0.20 e Å⁻³
230 parameters	Δρ_min = −0.21 e Å⁻³
45 restraints	Absolute structure: Flack (1983), 1631 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.05 (13)

Crystal data top

C₂₀H₁₃N₃S	V = 1613.7 (2) Å³
M_r = 327.39	Z = 4
Orthorhombic, P2₁2₁2	Mo Kα radiation
a = 19.7715 (17) Å	µ = 0.21 mm⁻¹
b = 8.7735 (7) Å	T = 293 K
c = 9.3027 (8) Å	0.32 × 0.30 × 0.24 mm

Data collection top

Bruker SMART area-detector diffractometer	3670 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2414 reflections with I > 2σ(I)
T_min = 0.937, T_max = 0.952	R_int = 0.045
10809 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	H-atom parameters constrained
wR(F²) = 0.128	Δρ_max = 0.20 e Å⁻³
S = 1.03	Δρ_min = −0.21 e Å⁻³
3670 reflections	Absolute structure: Flack (1983), 1631 Friedel pairs
230 parameters	Absolute structure parameter: 0.05 (13)
45 restraints

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	0.59650 (8)	0.46180 (17)	0.63475 (18)	0.0639 (5)	0.731 (3)
S1'	0.5970 (3)	0.1599 (5)	0.7573 (7)	0.0639 (5)	0.27
N1	0.50872 (10)	0.2300 (3)	0.3908 (2)	0.0425 (6)
N2	0.41393 (12)	0.1323 (3)	0.4794 (3)	0.0563 (7)
N3	0.45695 (12)	0.1669 (3)	0.5908 (3)	0.0555 (7)
C1	0.55374 (13)	0.2743 (3)	0.2800 (3)	0.0468 (7)
C2	0.52959 (14)	0.2706 (4)	0.1445 (3)	0.0583 (8)
H2	0.5581	0.3016	0.0707	0.070*
C3	0.46266 (14)	0.2218 (4)	0.1071 (3)	0.0563 (8)
C4	0.43864 (17)	0.2247 (5)	−0.0345 (4)	0.0718 (10)
H4	0.4665	0.2600	−0.1078	0.086*
C5	0.37500 (18)	0.1765 (4)	−0.0660 (4)	0.0746 (11)
H5	0.3598	0.1784	−0.1607	0.090*
C6	0.33259 (17)	0.1246 (4)	0.0419 (4)	0.0715 (10)
H6	0.2891	0.0924	0.0193	0.086*
C7	0.35420 (15)	0.1203 (4)	0.1817 (4)	0.0615 (9)
H7	0.3254	0.0858	0.2538	0.074*
C8	0.41991 (14)	0.1682 (3)	0.2156 (3)	0.0483 (7)
C9	0.44535 (13)	0.1724 (3)	0.3605 (3)	0.0449 (7)
C10	0.51257 (13)	0.2250 (3)	0.5399 (3)	0.0448 (7)
C11	0.56696 (13)	0.2788 (3)	0.6329 (3)	0.0492 (7)
C12	0.5985 (3)	0.2087 (6)	0.7424 (7)	0.0665 (19)	0.731 (3)
H12	0.5866	0.1084	0.7623	0.080*	0.731 (3)
C13	0.6458 (4)	0.2730 (7)	0.8243 (11)	0.0695 (18)	0.731 (3)
H13	0.6711	0.2269	0.8965	0.083*	0.731 (3)
C14	0.6491 (3)	0.4187 (7)	0.7808 (6)	0.0649 (19)	0.731 (3)
H14	0.6770	0.4906	0.8243	0.078*	0.731 (3)
C12'	0.5862 (10)	0.4243 (14)	0.659 (2)	0.0665 (19)	0.27
H12'	0.5619	0.5062	0.6221	0.080*	0.269 (3)
C13'	0.6415 (10)	0.447 (3)	0.740 (2)	0.0695 (18)	0.27
H13'	0.6697	0.5313	0.7463	0.083*	0.269 (3)
C14'	0.6445 (15)	0.3135 (19)	0.811 (3)	0.0649 (19)	0.27
H14B	0.6729	0.3042	0.8903	0.078*	0.269 (3)
C15	0.62471 (13)	0.3176 (3)	0.3121 (3)	0.0460 (7)
C16	0.66749 (13)	0.2237 (3)	0.3895 (3)	0.0491 (7)
H16	0.6519	0.1311	0.4251	0.059*
C17	0.73382 (14)	0.2682 (4)	0.4135 (3)	0.0565 (8)
H17	0.7625	0.2051	0.4657	0.068*
C18	0.75759 (15)	0.4039 (4)	0.3615 (4)	0.0634 (9)
H18	0.8019	0.4337	0.3797	0.076*
C19	0.71543 (15)	0.4960 (4)	0.2821 (4)	0.0659 (9)
H19	0.7315	0.5875	0.2449	0.079*
C20	0.64940 (14)	0.4525 (4)	0.2576 (3)	0.0569 (8)
H20	0.6212	0.5150	0.2036	0.068*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0616 (8)	0.0510 (8)	0.0790 (10)	−0.0019 (6)	−0.0066 (7)	−0.0081 (7)
S1'	0.0616 (8)	0.0510 (8)	0.0790 (10)	−0.0019 (6)	−0.0066 (7)	−0.0081 (7)
N1	0.0383 (11)	0.0443 (14)	0.0448 (14)	0.0009 (10)	0.0050 (10)	0.0028 (11)
N2	0.0483 (14)	0.0649 (16)	0.0557 (16)	−0.0058 (12)	0.0043 (13)	0.0079 (13)
N3	0.0510 (14)	0.0667 (17)	0.0489 (15)	−0.0028 (13)	0.0059 (12)	0.0061 (13)
C1	0.0424 (14)	0.0469 (15)	0.0511 (18)	0.0034 (13)	0.0072 (13)	0.0010 (15)
C2	0.0534 (17)	0.077 (2)	0.0448 (18)	−0.0024 (16)	0.0093 (14)	0.0053 (17)
C3	0.0519 (17)	0.067 (2)	0.0497 (19)	0.0066 (15)	−0.0018 (14)	−0.0057 (16)
C4	0.064 (2)	0.100 (3)	0.051 (2)	0.009 (2)	0.0022 (17)	−0.004 (2)
C5	0.067 (2)	0.101 (3)	0.056 (2)	0.014 (2)	−0.0124 (18)	−0.015 (2)
C6	0.056 (2)	0.078 (2)	0.080 (3)	0.0023 (18)	−0.018 (2)	−0.014 (2)
C7	0.0504 (18)	0.067 (2)	0.067 (2)	−0.0026 (16)	−0.0045 (15)	0.0007 (17)
C8	0.0467 (16)	0.0454 (16)	0.0529 (18)	0.0058 (13)	0.0007 (14)	−0.0047 (14)
C9	0.0413 (14)	0.0432 (16)	0.0501 (17)	−0.0003 (12)	0.0024 (14)	0.0033 (14)
C10	0.0472 (15)	0.0431 (16)	0.0440 (17)	0.0028 (13)	0.0045 (13)	0.0023 (14)
C11	0.0463 (15)	0.0544 (17)	0.0470 (17)	0.0081 (13)	0.0031 (13)	−0.0061 (15)
C12	0.073 (3)	0.045 (3)	0.082 (4)	0.002 (3)	0.012 (3)	0.011 (3)
C13	0.054 (3)	0.091 (4)	0.064 (3)	0.015 (4)	−0.004 (2)	−0.002 (4)
C14	0.063 (3)	0.068 (4)	0.063 (4)	0.005 (3)	−0.019 (3)	−0.021 (3)
C12'	0.073 (3)	0.045 (3)	0.082 (4)	0.002 (3)	0.012 (3)	0.011 (3)
C13'	0.054 (3)	0.091 (4)	0.064 (3)	0.015 (4)	−0.004 (2)	−0.002 (4)
C14'	0.063 (3)	0.068 (4)	0.063 (4)	0.005 (3)	−0.019 (3)	−0.021 (3)
C15	0.0441 (14)	0.0470 (17)	0.0471 (17)	−0.0013 (13)	0.0073 (13)	−0.0016 (13)
C16	0.0470 (15)	0.0484 (16)	0.0520 (18)	0.0027 (14)	0.0057 (14)	0.0051 (14)
C17	0.0451 (15)	0.069 (2)	0.0555 (18)	0.0142 (16)	0.0029 (13)	−0.0004 (17)
C18	0.0441 (17)	0.080 (2)	0.066 (2)	−0.0092 (16)	0.0086 (16)	−0.0034 (19)
C19	0.0613 (19)	0.063 (2)	0.074 (2)	−0.0157 (17)	0.0121 (17)	0.0096 (18)
C20	0.0518 (17)	0.0544 (18)	0.064 (2)	−0.0016 (15)	0.0031 (15)	0.0112 (16)

Geometric parameters (Å, º) top

S1—C11	1.708 (3)	C10—C11	1.459 (4)
S1—C14	1.752 (4)	C11—C12	1.344 (5)
S1'—C11	1.667 (5)	C11—C12'	1.355 (8)
S1'—C14'	1.717 (9)	C12—C13	1.331 (6)
N1—C9	1.380 (3)	C12—H12	0.9300
N1—C10	1.389 (3)	C13—C14	1.342 (6)
N1—C1	1.417 (3)	C13—H13	0.9300
N2—C9	1.316 (4)	C14—H14	0.9300
N2—N3	1.375 (3)	C12'—C13'	1.343 (8)
N3—C10	1.301 (3)	C12'—H12'	0.9300
C1—C2	1.348 (4)	C13'—C14'	1.342 (8)
C1—C15	1.484 (4)	C13'—H13'	0.9300
C2—C3	1.434 (4)	C14'—H14B	0.9300
C2—H2	0.9300	C15—C20	1.377 (4)
C3—C8	1.398 (4)	C15—C16	1.383 (4)
C3—C4	1.400 (4)	C16—C17	1.387 (4)
C4—C5	1.359 (5)	C16—H16	0.9300
C4—H4	0.9300	C17—C18	1.368 (4)
C5—C6	1.385 (5)	C17—H17	0.9300
C5—H5	0.9300	C18—C19	1.376 (4)
C6—C7	1.369 (5)	C18—H18	0.9300
C6—H6	0.9300	C19—C20	1.379 (4)
C7—C8	1.402 (4)	C19—H19	0.9300
C7—H7	0.9300	C20—H20	0.9300
C8—C9	1.439 (4)

C11—S1—C14	90.5 (2)	C10—C11—S1'	118.2 (3)
C11—S1'—C14'	84.6 (8)	C12—C11—S1	105.3 (3)
C9—N1—C10	104.0 (2)	C10—C11—S1	124.2 (2)
C9—N1—C1	121.5 (2)	S1'—C11—S1	117.3 (2)
C10—N1—C1	134.5 (2)	C13—C12—C11	124.5 (5)
C9—N2—N3	106.4 (2)	C13—C12—H12	117.8
C10—N3—N2	109.6 (2)	C11—C12—H12	117.8
C2—C1—N1	116.8 (2)	C12—C13—C14	105.4 (6)
C2—C1—C15	122.0 (3)	C12—C13—H13	127.3
N1—C1—C15	121.2 (2)	C14—C13—H13	127.3
C1—C2—C3	124.2 (3)	C13—C14—S1	114.2 (5)
C1—C2—H2	117.9	C13—C14—H14	122.9
C3—C2—H2	117.9	S1—C14—H14	122.9
C8—C3—C4	118.7 (3)	C13'—C12'—C11	118.0 (17)
C8—C3—C2	118.9 (3)	C13'—C12'—H12'	121.0
C4—C3—C2	122.4 (3)	C11—C12'—H12'	121.0
C5—C4—C3	120.8 (3)	C14'—C13'—C12'	100.6 (19)
C5—C4—H4	119.6	C14'—C13'—H13'	129.7
C3—C4—H4	119.6	C12'—C13'—H13'	129.7
C4—C5—C6	120.4 (3)	C13'—C14'—S1'	121.1 (17)
C4—C5—H5	119.8	C13'—C14'—H14B	119.4
C6—C5—H5	119.8	S1'—C14'—H14B	119.4
C7—C6—C5	120.6 (3)	C20—C15—C16	119.1 (3)
C7—C6—H6	119.7	C20—C15—C1	118.8 (3)
C5—C6—H6	119.7	C16—C15—C1	122.0 (3)
C6—C7—C8	119.7 (3)	C15—C16—C17	119.6 (3)
C6—C7—H7	120.2	C15—C16—H16	120.2
C8—C7—H7	120.2	C17—C16—H16	120.2
C3—C8—C7	119.9 (3)	C18—C17—C16	120.9 (3)
C3—C8—C9	117.2 (2)	C18—C17—H17	119.6
C7—C8—C9	122.8 (3)	C16—C17—H17	119.6
N2—C9—N1	110.8 (3)	C17—C18—C19	119.5 (3)
N2—C9—C8	127.9 (2)	C17—C18—H18	120.2
N1—C9—C8	121.2 (3)	C19—C18—H18	120.2
N3—C10—N1	109.2 (2)	C18—C19—C20	120.0 (3)
N3—C10—C11	122.3 (2)	C18—C19—H19	120.0
N1—C10—C11	128.5 (2)	C20—C19—H19	120.0
C12—C11—C12'	99.4 (9)	C19—C20—C15	120.9 (3)
C12—C11—C10	130.1 (3)	C19—C20—H20	119.6
C12'—C11—C10	128.3 (9)	C15—C20—H20	119.6
C12'—C11—S1'	111.4 (9)

C9—N2—N3—C10	−0.4 (3)	N1—C10—C11—C12'	69.1 (13)
C9—N1—C1—C2	5.9 (4)	N3—C10—C11—S1'	53.0 (4)
C10—N1—C1—C2	−176.4 (3)	N1—C10—C11—S1'	−129.4 (4)
C9—N1—C1—C15	−172.2 (2)	N3—C10—C11—S1	−120.4 (3)
C10—N1—C1—C15	5.5 (5)	N1—C10—C11—S1	57.2 (4)
N1—C1—C2—C3	−1.5 (5)	C14'—S1'—C11—C12	−2 (3)
C15—C1—C2—C3	176.5 (3)	C14'—S1'—C11—C12'	−10.5 (17)
C1—C2—C3—C8	−2.8 (5)	C14'—S1'—C11—C10	−175.0 (13)
C1—C2—C3—C4	177.7 (4)	C14'—S1'—C11—S1	−1.1 (13)
C8—C3—C4—C5	0.0 (5)	C14—S1—C11—C12	1.2 (5)
C2—C3—C4—C5	179.6 (3)	C14—S1—C11—C12'	58 (5)
C3—C4—C5—C6	0.5 (6)	C14—S1—C11—C10	174.5 (3)
C4—C5—C6—C7	−0.3 (6)	C14—S1—C11—S1'	1.0 (4)
C5—C6—C7—C8	−0.3 (5)	C12'—C11—C12—C13	−12.8 (12)
C4—C3—C8—C7	−0.6 (5)	C10—C11—C12—C13	−176.7 (7)
C2—C3—C8—C7	179.8 (3)	S1'—C11—C12—C13	175 (3)
C4—C3—C8—C9	−177.6 (3)	S1—C11—C12—C13	−4.0 (9)
C2—C3—C8—C9	2.8 (4)	C11—C12—C13—C14	4.9 (11)
C6—C7—C8—C3	0.8 (5)	C12—C13—C14—S1	−3.3 (8)
C6—C7—C8—C9	177.6 (3)	C11—S1—C14—C13	1.3 (5)
N3—N2—C9—N1	1.2 (3)	C12—C11—C12'—C13'	21 (2)
N3—N2—C9—C8	−175.8 (3)	C10—C11—C12'—C13'	−174.8 (14)
C10—N1—C9—N2	−1.4 (3)	S1'—C11—C12'—C13'	23 (2)
C1—N1—C9—N2	176.9 (2)	S1—C11—C12'—C13'	−104 (6)
C10—N1—C9—C8	175.8 (3)	C11—C12'—C13'—C14'	−22 (3)
C1—N1—C9—C8	−5.9 (4)	C12'—C13'—C14'—S1'	13 (3)
C3—C8—C9—N2	178.0 (3)	C11—S1'—C14'—C13'	−2 (3)
C7—C8—C9—N2	1.2 (5)	C2—C1—C15—C20	52.5 (4)
C3—C8—C9—N1	1.3 (4)	N1—C1—C15—C20	−129.5 (3)
C7—C8—C9—N1	−175.5 (3)	C2—C1—C15—C16	−124.6 (4)
N2—N3—C10—N1	−0.5 (3)	N1—C1—C15—C16	53.4 (4)
N2—N3—C10—C11	177.5 (3)	C20—C15—C16—C17	1.4 (4)
C9—N1—C10—N3	1.2 (3)	C1—C15—C16—C17	178.5 (3)
C1—N1—C10—N3	−176.9 (3)	C15—C16—C17—C18	−0.1 (4)
C9—N1—C10—C11	−176.6 (3)	C16—C17—C18—C19	−1.2 (5)
C1—N1—C10—C11	5.3 (5)	C17—C18—C19—C20	1.1 (5)
N3—C10—C11—C12	51.1 (6)	C18—C19—C20—C15	0.2 (5)
N1—C10—C11—C12	−131.3 (5)	C16—C15—C20—C19	−1.5 (4)
N3—C10—C11—C12'	−108.5 (13)	C1—C15—C20—C19	−178.7 (3)

Experimental details

Crystal data
Chemical formula	C₂₀H₁₃N₃S
M_r	327.39
Crystal system, space group	Orthorhombic, P2₁2₁2
Temperature (K)	293
a, b, c (Å)	19.7715 (17), 8.7735 (7), 9.3027 (8)
V (Å³)	1613.7 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.32 × 0.30 × 0.24

Data collection
Diffractometer	Bruker SMART area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.937, 0.952
No. of measured, independent and observed [I > 2σ(I)] reflections	10809, 3670, 2414
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.128, 1.03
No. of reflections	3670
No. of parameters	230
No. of restraints	45
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.21
Absolute structure	Flack (1983), 1631 Friedel pairs
Absolute structure parameter	0.05 (13)

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Acknowledgements

We thank the Department of Science and Technology, India, for use of the diffraction facility at IISc under the IRHPA–DST program; FNK thanks the DST for Fast Track Proposal funding. We thank VIT University and the University of Malaya for supporting this study.

References

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