(2E)-3-[4-(Benz­yloxy)phen­yl]-1-(pyridin-3-yl)prop-2-en-1-one

Fun, H.-K.; Quah, C.K.; Nayak, P.S.; Narayana, B.; Sarojini, B.K.

doi:10.1107/S1600536812034897

organic compounds

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ISSN: 2056-9890

Volume 68| Part 9| September 2012| Page o2724

doi:10.1107/S1600536812034897

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(2E)-3-[4-(Benzyloxy)phenyl]-1-(pyridin-3-yl)prop-2-en-1-one

Hoong-Kun Fun,^a ^*‡ Ching Kheng Quah,^a § Prakash S. Nayak,^b B. Narayana ^b and B. K. Sarojini ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, and ^cDepartment of Chemistry, P. A. College of Engineering, Nadupadavu, Mangalore 574 153, India
^*Correspondence e-mail: hkfun@usm.my

(Received 31 July 2012; accepted 7 August 2012; online 15 August 2012)

The title compound, C₂₁H₁₇NO₂, exists in an E conformation with respect to the C=C bond. The pyridine ring forms dihedral angles of 5.57 (7) and 82.30 (9)°, respectively, with the central benzene ring and the terminal phenyl ring. The dihedral angle between the benzene and phenyl rings is 87.69 (8)°. No significant intermolecular interactions are observed.

Related literature

For the pharmacological activity of chalcones, see: Matsuda et al. (2003 ); Lopez et al. (2001 ); Agarwal et al. (2005 ). For related structures, see: Bibila Mayaya Bisseyou et al. (2007 ); Liu et al. (2005 ); Jasinski et al. (2011 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₁H₁₇NO₂
M_r = 315.36
Monoclinic, P 2₁ /c
a = 5.9845 (6) Å
b = 38.187 (4) Å
c = 8.5412 (7) Å
β = 123.372 (5)°
V = 1630.1 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.40 × 0.33 × 0.17 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.968, T_max = 0.986
18812 measured reflections
4751 independent reflections
3171 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.141
S = 1.02
4751 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812034897/is5181sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812034897/is5181Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812034897/is5181Isup3.cml

checkCIF report

Comment top

Chalcones constitute an important family of substances belonging to flavonoids and isoflavonoids and are abundant in edible plants. Chalcones exhibit many pharmacological activities, including anti-leishmanial, anti-inflammatory (Matsuda et al., 2003), anti-mitotic, anti-invasive, anti-tuberculosis, anti-fungal (Lopez et al., 2001) and anti-malarial (Agarwal et al., 2005). Nitrogen moiety containing heterocyclic chalcones plays important roles as anti-ulcer, herbicidal, anti-bacterial, analgesic, sedative, anti-phlogistic and virucidal agents. The crystal structures of some chalcones derived from acetyl pyridine viz., (Z)-3-(2,6-dichlorophenyl)-1-(pyridin-3-yl)-2- (1H-1,2,4-triazol-1-yl)prop-2-en-1-one (Liu et al., 2005), 3-(3-chlorophenyl)-1-(2-methylimidazo[1,2-a]pyridin-3-yl)prop-2-en-1-one (Bibila Mayaya Bisseyou et al., 2007) and (2E)-3-(3-bromo-4-methoxyphenyl)-1-(pyridin-2-yl)prop-2-en-1-one (Jasinski et al., 2011) have been reported. In continuation of our studies on chalcones and their derivatives, the title compound (I) was prepared and its crystal structure is reported.

The title compound (Fig. 1) exists in an E configuration with respect to the C14═C15 bond [1.3217 (19) Å]. The pyridin-3-yl ring (N1/C17–C21) forms dihedral angles of 5.57 (7) and 82.30 (9)° with the benzene (C8–C13) and phenyl (C1–C6) rings, respectively. The dihedral angle between the benzene and phenyl rings is 87.69 (8)°. Bond lengths and angles are within normal ranges and are comparable to related structures (Bibila Mayaya Bisseyou et al., 2007; Liu et al., 2005; Jasinski et al., 2011). No significant intermolecular hydrogen bonds are observed.

Related literature top

For the pharmacological activity of chalcones, see: Matsuda et al. (2003); Lopez et al. (2001); Agarwal et al. (2005). For related structures, see: Bibila Mayaya Bisseyou et al. (2007); Liu et al. (2005); Jasinski et al. (2011). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

To a mixture of 3-acetylpyridine (1.1 mL, 0.01 mol) and 4-benzyloxybenzaldehyde (2.12 g, 0.01 mol) in ethanol (100 mL), 15 mL of 10% sodium hydroxide solution was added and stirred at 0–5 °C for 3 h. The precipitate formed was collected by filtration and purified by recrystallization from ethanol. Single crystals were grown from acetone and toluene (1:1) mixture by slow evaporation method (m.p. 403–407 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: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

Fig. 1. The molecular structure of the title compound showing 30% probability displacement ellipsoids for non-H atoms.

(2E)-3-[4-(Benzyloxy)phenyl]-1-(pyridin-3-yl)prop-2-en-1-one top

Crystal data top

C₂₁H₁₇NO₂	F(000) = 664
M_r = 315.36	D_x = 1.285 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4372 reflections
a = 5.9845 (6) Å	θ = 2.9–26.5°
b = 38.187 (4) Å	µ = 0.08 mm⁻¹
c = 8.5412 (7) Å	T = 100 K
β = 123.372 (5)°	Block, yellow
V = 1630.1 (3) Å³	0.40 × 0.33 × 0.17 mm
Z = 4

Data collection top

Bruker SMART APEXII DUO CCD area-detector diffractometer	4751 independent reflections
Radiation source: fine-focus sealed tube	3171 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ϕ and ω scans	θ_max = 30.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→8
T_min = 0.968, T_max = 0.986	k = −53→47
18812 measured reflections	l = −11→11

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.141	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.059P)² + 0.2532P] where P = (F_o² + 2F_c²)/3
4751 reflections	(Δ/σ)_max = 0.001
217 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₂₁H₁₇NO₂	V = 1630.1 (3) Å³
M_r = 315.36	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.9845 (6) Å	µ = 0.08 mm⁻¹
b = 38.187 (4) Å	T = 100 K
c = 8.5412 (7) Å	0.40 × 0.33 × 0.17 mm
β = 123.372 (5)°

Data collection top

Bruker SMART APEXII DUO CCD area-detector diffractometer	4751 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3171 reflections with I > 2σ(I)
T_min = 0.968, T_max = 0.986	R_int = 0.028
18812 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.141	H-atom parameters constrained
S = 1.02	Δρ_max = 0.17 e Å⁻³
4751 reflections	Δρ_min = −0.15 e Å⁻³
217 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	−0.1642 (2)	−0.12817 (2)	0.76557 (15)	0.0534 (3)
O2	0.6625 (3)	0.04322 (3)	0.69065 (19)	0.0690 (3)
N1	0.5921 (3)	0.14650 (3)	0.7813 (2)	0.0668 (4)
C1	−0.2000 (4)	−0.20724 (4)	0.8950 (3)	0.0637 (4)
H1A	−0.0178	−0.2048	0.9949	0.076*
C2	−0.3631 (4)	−0.23073 (4)	0.9115 (3)	0.0725 (5)
H2A	−0.2924	−0.2442	1.0225	0.087*
C3	−0.6271 (4)	−0.23442 (4)	0.7671 (3)	0.0700 (5)
H3A	−0.7382	−0.2506	0.7778	0.084*
C4	−0.7299 (4)	−0.21464 (4)	0.6074 (3)	0.0673 (4)
H4A	−0.9128	−0.2169	0.5085	0.081*
C5	−0.5668 (3)	−0.19132 (4)	0.5905 (2)	0.0583 (4)
H5A	−0.6381	−0.1779	0.4792	0.070*
C6	−0.3010 (3)	−0.18749 (3)	0.7344 (2)	0.0496 (3)
C7	−0.1254 (3)	−0.16226 (3)	0.7147 (2)	0.0524 (3)
H7A	0.0645	−0.1693	0.7978	0.063*
H7B	−0.1734	−0.1621	0.5838	0.063*
C8	−0.0323 (3)	−0.10096 (3)	0.74586 (18)	0.0425 (3)
C9	−0.0638 (3)	−0.06836 (3)	0.8049 (2)	0.0480 (3)
H9A	−0.1686	−0.0664	0.8569	0.058*
C10	0.0551 (3)	−0.03911 (3)	0.7886 (2)	0.0467 (3)
H10A	0.0300	−0.0170	0.8282	0.056*
C11	0.2133 (2)	−0.04140 (3)	0.71422 (18)	0.0427 (3)
C12	0.2424 (3)	−0.07406 (3)	0.65656 (19)	0.0485 (3)
H12A	0.3472	−0.0761	0.6045	0.058*
C13	0.1238 (3)	−0.10387 (4)	0.6723 (2)	0.0484 (3)
H13A	0.1490	−0.1260	0.6332	0.058*
C14	0.3499 (3)	−0.01114 (3)	0.69900 (19)	0.0467 (3)
H14A	0.4507	−0.0153	0.6454	0.056*
C15	0.3490 (3)	0.02140 (4)	0.7514 (2)	0.0507 (3)
H15A	0.2462	0.0269	0.8021	0.061*
C16	0.5021 (3)	0.04934 (4)	0.73355 (19)	0.0470 (3)
C17	0.4655 (3)	0.08627 (3)	0.77386 (18)	0.0433 (3)
C18	0.6038 (3)	0.11266 (4)	0.7499 (2)	0.0562 (4)
H18A	0.7154	0.1060	0.7079	0.067*
C19	0.4329 (4)	0.15510 (4)	0.8397 (2)	0.0652 (4)
H19A	0.4199	0.1791	0.8629	0.078*
C20	0.2878 (4)	0.13133 (4)	0.8679 (3)	0.0687 (5)
H20A	0.1783	0.1388	0.9103	0.082*
C21	0.3026 (3)	0.09635 (4)	0.8339 (2)	0.0579 (4)
H21A	0.2022	0.0794	0.8516	0.069*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0640 (6)	0.0392 (5)	0.0748 (7)	−0.0061 (4)	0.0494 (6)	−0.0041 (4)
O2	0.0864 (8)	0.0557 (6)	0.1028 (9)	−0.0082 (5)	0.0761 (8)	−0.0071 (6)
N1	0.0781 (10)	0.0477 (7)	0.0865 (10)	−0.0058 (6)	0.0528 (9)	0.0013 (6)
C1	0.0684 (10)	0.0500 (8)	0.0743 (10)	0.0020 (7)	0.0402 (9)	0.0058 (7)
C2	0.0935 (14)	0.0524 (9)	0.0850 (12)	0.0029 (9)	0.0576 (12)	0.0134 (8)
C3	0.0904 (13)	0.0484 (8)	0.0985 (13)	−0.0127 (8)	0.0693 (12)	−0.0046 (8)
C4	0.0667 (10)	0.0617 (9)	0.0824 (12)	−0.0148 (8)	0.0466 (9)	−0.0097 (8)
C5	0.0647 (10)	0.0507 (8)	0.0662 (9)	−0.0047 (7)	0.0403 (8)	−0.0012 (7)
C6	0.0615 (9)	0.0347 (6)	0.0651 (9)	−0.0013 (6)	0.0427 (8)	−0.0047 (6)
C7	0.0595 (9)	0.0414 (7)	0.0660 (9)	−0.0045 (6)	0.0407 (8)	−0.0062 (6)
C8	0.0407 (7)	0.0410 (6)	0.0458 (7)	−0.0022 (5)	0.0237 (6)	0.0015 (5)
C9	0.0504 (8)	0.0456 (7)	0.0593 (8)	0.0005 (6)	0.0372 (7)	0.0008 (6)
C10	0.0479 (7)	0.0395 (6)	0.0576 (8)	0.0009 (5)	0.0321 (7)	0.0009 (5)
C11	0.0384 (6)	0.0453 (7)	0.0424 (6)	−0.0012 (5)	0.0209 (6)	0.0035 (5)
C12	0.0489 (8)	0.0525 (7)	0.0535 (8)	−0.0048 (6)	0.0342 (7)	−0.0043 (6)
C13	0.0510 (8)	0.0446 (7)	0.0555 (8)	−0.0037 (6)	0.0330 (7)	−0.0067 (6)
C14	0.0465 (7)	0.0492 (7)	0.0482 (7)	−0.0024 (6)	0.0284 (6)	0.0036 (6)
C15	0.0560 (8)	0.0477 (7)	0.0596 (8)	−0.0048 (6)	0.0390 (7)	0.0015 (6)
C16	0.0510 (8)	0.0485 (7)	0.0486 (7)	−0.0030 (6)	0.0320 (6)	0.0021 (6)
C17	0.0433 (7)	0.0467 (7)	0.0409 (6)	−0.0022 (5)	0.0238 (6)	0.0033 (5)
C18	0.0607 (9)	0.0508 (8)	0.0707 (10)	−0.0041 (6)	0.0447 (8)	0.0024 (7)
C19	0.0721 (11)	0.0509 (8)	0.0724 (11)	−0.0003 (7)	0.0397 (9)	−0.0062 (7)
C20	0.0771 (11)	0.0644 (10)	0.0856 (12)	−0.0041 (8)	0.0582 (10)	−0.0135 (8)
C21	0.0640 (9)	0.0580 (8)	0.0682 (9)	−0.0079 (7)	0.0469 (8)	−0.0041 (7)

Geometric parameters (Å, º) top

O1—C8	1.3700 (15)	C9—H9A	0.9500
O1—C7	1.4313 (15)	C10—C11	1.4037 (18)
O2—C16	1.2235 (16)	C10—H10A	0.9500
N1—C18	1.3297 (19)	C11—C12	1.3869 (18)
N1—C19	1.337 (2)	C11—C14	1.4620 (17)
C1—C6	1.380 (2)	C12—C13	1.3866 (18)
C1—C2	1.388 (2)	C12—H12A	0.9500
C1—H1A	0.9500	C13—H13A	0.9500
C2—C3	1.376 (3)	C14—C15	1.3217 (19)
C2—H2A	0.9500	C14—H14A	0.9500
C3—C4	1.373 (3)	C15—C16	1.4682 (18)
C3—H3A	0.9500	C15—H15A	0.9500
C4—C5	1.386 (2)	C16—C17	1.4963 (18)
C4—H4A	0.9500	C17—C21	1.3826 (19)
C5—C6	1.383 (2)	C17—C18	1.3889 (18)
C5—H5A	0.9500	C18—H18A	0.9500
C6—C7	1.5019 (18)	C19—C20	1.366 (2)
C7—H7A	0.9900	C19—H19A	0.9500
C7—H7B	0.9900	C20—C21	1.380 (2)
C8—C13	1.3877 (18)	C20—H20A	0.9500
C8—C9	1.3943 (18)	C21—H21A	0.9500
C9—C10	1.3718 (18)

C8—O1—C7	116.85 (10)	C11—C10—H10A	119.6
C18—N1—C19	116.22 (13)	C12—C11—C10	117.68 (11)
C6—C1—C2	120.41 (17)	C12—C11—C14	119.58 (12)
C6—C1—H1A	119.8	C10—C11—C14	122.73 (12)
C2—C1—H1A	119.8	C13—C12—C11	122.20 (12)
C3—C2—C1	119.97 (16)	C13—C12—H12A	118.9
C3—C2—H2A	120.0	C11—C12—H12A	118.9
C1—C2—H2A	120.0	C12—C13—C8	119.10 (12)
C4—C3—C2	120.02 (15)	C12—C13—H13A	120.4
C4—C3—H3A	120.0	C8—C13—H13A	120.4
C2—C3—H3A	120.0	C15—C14—C11	127.31 (12)
C3—C4—C5	120.03 (17)	C15—C14—H14A	116.3
C3—C4—H4A	120.0	C11—C14—H14A	116.3
C5—C4—H4A	120.0	C14—C15—C16	121.93 (13)
C6—C5—C4	120.44 (16)	C14—C15—H15A	119.0
C6—C5—H5A	119.8	C16—C15—H15A	119.0
C4—C5—H5A	119.8	O2—C16—C15	121.97 (13)
C1—C6—C5	119.13 (14)	O2—C16—C17	119.18 (12)
C1—C6—C7	120.75 (14)	C15—C16—C17	118.83 (11)
C5—C6—C7	120.12 (13)	C21—C17—C18	116.88 (13)
O1—C7—C6	108.00 (11)	C21—C17—C16	124.77 (12)
O1—C7—H7A	110.1	C18—C17—C16	118.36 (11)
C6—C7—H7A	110.1	N1—C18—C17	124.98 (14)
O1—C7—H7B	110.1	N1—C18—H18A	117.5
C6—C7—H7B	110.1	C17—C18—H18A	117.5
H7A—C7—H7B	108.4	N1—C19—C20	123.70 (15)
O1—C8—C13	124.89 (11)	N1—C19—H19A	118.2
O1—C8—C9	115.53 (11)	C20—C19—H19A	118.2
C13—C8—C9	119.58 (12)	C19—C20—C21	119.08 (15)
C10—C9—C8	120.64 (12)	C19—C20—H20A	120.5
C10—C9—H9A	119.7	C21—C20—H20A	120.5
C8—C9—H9A	119.7	C20—C21—C17	119.14 (14)
C9—C10—C11	120.79 (12)	C20—C21—H21A	120.4
C9—C10—H10A	119.6	C17—C21—H21A	120.4

C6—C1—C2—C3	0.0 (3)	C11—C12—C13—C8	0.9 (2)
C1—C2—C3—C4	−0.6 (3)	O1—C8—C13—C12	178.71 (12)
C2—C3—C4—C5	0.9 (3)	C9—C8—C13—C12	−0.9 (2)
C3—C4—C5—C6	−0.7 (2)	C12—C11—C14—C15	−178.19 (14)
C2—C1—C6—C5	0.2 (2)	C10—C11—C14—C15	0.7 (2)
C2—C1—C6—C7	−179.44 (14)	C11—C14—C15—C16	178.09 (13)
C4—C5—C6—C1	0.1 (2)	C14—C15—C16—O2	−8.9 (2)
C4—C5—C6—C7	179.77 (13)	C14—C15—C16—C17	172.68 (13)
C8—O1—C7—C6	−176.20 (12)	O2—C16—C17—C21	−176.13 (15)
C1—C6—C7—O1	−96.55 (15)	C15—C16—C17—C21	2.4 (2)
C5—C6—C7—O1	83.83 (16)	O2—C16—C17—C18	3.9 (2)
C7—O1—C8—C13	3.3 (2)	C15—C16—C17—C18	−177.67 (13)
C7—O1—C8—C9	−177.05 (12)	C19—N1—C18—C17	−0.2 (3)
O1—C8—C9—C10	−178.79 (12)	C21—C17—C18—N1	0.4 (2)
C13—C8—C9—C10	0.9 (2)	C16—C17—C18—N1	−179.58 (15)
C8—C9—C10—C11	−0.7 (2)	C18—N1—C19—C20	0.2 (3)
C9—C10—C11—C12	0.6 (2)	N1—C19—C20—C21	−0.4 (3)
C9—C10—C11—C14	−178.24 (13)	C19—C20—C21—C17	0.5 (3)
C10—C11—C12—C13	−0.7 (2)	C18—C17—C21—C20	−0.5 (2)
C14—C11—C12—C13	178.21 (13)	C16—C17—C21—C20	179.44 (15)

Experimental details

Crystal data
Chemical formula	C₂₁H₁₇NO₂
M_r	315.36
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	5.9845 (6), 38.187 (4), 8.5412 (7)
β (°)	123.372 (5)
V (Å³)	1630.1 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.40 × 0.33 × 0.17

Data collection
Diffractometer	Bruker SMART APEXII DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.968, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	18812, 4751, 3171
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.704

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.141, 1.02
No. of reflections	4751
No. of parameters	217
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.15

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: A-5525-2009.

Acknowledgements

The authors would like to thank Universiti Sains Malaysia (USM) for the Research University Grant (No. 1001/PFIZIK/811160). BN also thanks the UGC, New Delhi, and the Government of India for the purchase of chemicals through the SAP–DRS-Phase 1 programme.

References

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