1,2-Diphenyl-2-[4-(4-pyridyl)benzyl­idene­hydrazono]ethan-1-one

Patra, G.K.; Ng, S.W.

doi:10.1107/S1600536809026087

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o1810

doi:10.1107/S1600536809026087

Open

access

1,2-Diphenyl-2-[4-(4-pyridyl)benzylidenehydrazono]ethan-1-one

Goutam Kumar Patra ^a and Seik Weng Ng ^b ^*

^aDepartment of Chemistry, Vijaygarh Jyotish Ray College, 8/2 Vijaygarh, Jadavpur, Kolkata 700 032, India, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 24 June 2009; accepted 5 July 2009; online 11 July 2009)

In the title compound, C₂₆H₁₉N₃O, the dimethylene hydrazine (—C=N—N=C—) unit is approximately planar, the torsion angle around the N—N bond being 162.2 (6)°. The phenyl and benzoylphenyl rings at one end of the hydrazine unit are aligned at angles of 9.5 (5) and 88.5 (4)°, respectively, with respect to the hydrazine unit, whereas the benzene ring at the other end is twisted by an angle of 14.4 (4)°. In the crystal structure, molecules are linked into centrosymmetric dimers by intermolecular C—H⋯O hydrogen bonds. The monoclinic crystal under investigation shows pseudo-merohedral twinning with twin fractions of 0.63 and 0.37.

Related literature

For the crystal structures of other carbaldehyde N′-benzoyl-N′-phenylhydrazones, see: Abbasi et al. (2007 ); Chowdhury et al. (2003 ); Liu et al. (2007 ); Schweizer et al. (1987 ).

Experimental

Crystal data

C₂₆H₁₉N₃O
M_r = 389.44
Monoclinic, P 2₁ /c
a = 7.1182 (2) Å
b = 23.2745 (7) Å
c = 11.8040 (4) Å
β = 90.278 (2)°
V = 1955.6 (1) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 140 K
0.45 × 0.15 × 0.05 mm

Data collection

Bruker SMART APEX area-detector diffractometer
Absorption correction: none
11057 measured reflections
3433 independent reflections
2825 reflections with I > 2σ(I)
R_int = 0.054

Refinement

R[F² > 2σ(F²)] = 0.093
wR(F²) = 0.252
S = 1.08
3433 reflections
260 parameters
H-atom parameters constrained
Δρ_max = 0.63 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C26—H26⋯O1ⁱ	0.95	2.57	3.502 (7)	166
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); 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, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809026087/ci2837sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809026087/ci2837Isup2.hkl

checkCIF report

Related literature top

For the crystal structures of other carbaldehyde N'-benzoyl-N'-phenylhydrazones, see: Abbasi et al. (2007); Chowdhury et al. (2003); Liu et al. (2007); Schweizer et al. (1987).

Experimental top

Benzil monohydrazone (0.224 g, 1 mmol) was dissolved in methanol (20 ml) and to this was added 4-pyridylbenzaldehyde (0.183 g, 1 mmol). The resulting yellowish mixture was heated for 6 h. The solvent was evaporated and the solid was recrystallized from methanol in 80% yield; m.p. 461 K.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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, 2009).

Figures top

Fig. 1. Displacement ellipsoid plot (Barbour, 2001) of C₂₆H₁₉N₃O at the 70% probability level; H atoms are drawn as spheres of arbitrary radius.

1,2-Diphenyl-2-[4-(4-pyridyl)benzylidenehydrazono]ethan-1-one top

Crystal data top

C₂₆H₁₉N₃O	F(000) = 816
M_r = 389.44	D_x = 1.323 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2404 reflections
a = 7.1182 (2) Å	θ = 2.5–23.3°
b = 23.2745 (7) Å	µ = 0.08 mm⁻¹
c = 11.8040 (4) Å	T = 140 K
β = 90.278 (2)°	Prism, brown
V = 1955.6 (1) Å³	0.45 × 0.15 × 0.05 mm
Z = 4

Data collection top

Bruker SMART APEX area-detector diffractometer	2825 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.054
Graphite monochromator	θ_max = 25.0°, θ_min = 0.9°
ω scans	h = −8→8
11057 measured reflections	k = −27→27
3433 independent reflections	l = −13→14

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)] = 0.093	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.252	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.1142P)² + 4.6222P] where P = (F_o² + 2F_c²)/3
3433 reflections	(Δ/σ)_max = 0.001
260 parameters	Δρ_max = 0.63 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

C₂₆H₁₉N₃O	V = 1955.6 (1) Å³
M_r = 389.44	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.1182 (2) Å	µ = 0.08 mm⁻¹
b = 23.2745 (7) Å	T = 140 K
c = 11.8040 (4) Å	0.45 × 0.15 × 0.05 mm
β = 90.278 (2)°

Data collection top

Bruker SMART APEX area-detector diffractometer	2825 reflections with I > 2σ(I)
11057 measured reflections	R_int = 0.054
3433 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.093	0 restraints
wR(F²) = 0.252	H-atom parameters constrained
S = 1.08	Δρ_max = 0.63 e Å⁻³
3433 reflections	Δρ_min = −0.38 e Å⁻³
260 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	0.5484 (6)	0.38713 (17)	0.8664 (3)	0.0404 (10)
N1	0.2040 (9)	0.37367 (17)	0.7012 (4)	0.0419 (13)
N2	0.2387 (8)	0.43390 (17)	0.6961 (3)	0.0343 (11)
N3	0.2956 (9)	0.8061 (2)	0.3966 (4)	0.0487 (15)
C1	0.2861 (6)	0.41267 (14)	0.9747 (2)	0.0366 (15)
C2	0.3933 (5)	0.4384 (2)	1.0593 (3)	0.0541 (18)
H2	0.5266	0.4374	1.0554	0.065*
C3	0.3056 (6)	0.46560 (18)	1.1495 (3)	0.0542 (18)
H3	0.3789	0.4832	1.2074	0.065*
C4	0.1107 (6)	0.46707 (17)	1.1552 (3)	0.0477 (17)
H4	0.0507	0.4857	1.2169	0.057*
C5	0.0034 (5)	0.4413 (2)	1.0705 (4)	0.0566 (19)
H5	−0.1298	0.4424	1.0744	0.068*
C6	0.0911 (5)	0.41414 (17)	0.9803 (3)	0.0427 (15)
H6	0.0178	0.3966	0.9224	0.051*
C7	0.3789 (9)	0.3850 (2)	0.8787 (4)	0.0323 (13)
C8	0.2589 (8)	0.3512 (2)	0.7921 (4)	0.0276 (11)
C9	0.2362 (8)	0.2882 (2)	0.8099 (4)	0.0263 (11)
C10	0.1549 (8)	0.2553 (2)	0.7251 (5)	0.0346 (13)
H10	0.1065	0.2733	0.6589	0.041*
C11	0.1442 (9)	0.1956 (2)	0.7373 (5)	0.0386 (14)
H11	0.0916	0.1726	0.6787	0.046*
C12	0.2116 (10)	0.1704 (2)	0.8361 (5)	0.0387 (14)
H12	0.2102	0.1298	0.8435	0.046*
C13	0.2799 (9)	0.2034 (2)	0.9232 (5)	0.0379 (14)
H13	0.3164	0.1859	0.9925	0.045*
C14	0.2956 (9)	0.2619 (2)	0.9104 (4)	0.0366 (14)
H14	0.3470	0.2845	0.9700	0.044*
C15	0.2301 (10)	0.4523 (2)	0.5948 (4)	0.0415 (16)
H15	0.2082	0.4252	0.5360	0.050*
C16	0.2517 (9)	0.5124 (2)	0.5636 (4)	0.0350 (13)
C17	0.2450 (11)	0.5271 (2)	0.4494 (4)	0.0472 (18)
H17	0.2366	0.4978	0.3937	0.057*
C18	0.2504 (10)	0.5839 (2)	0.4160 (4)	0.0380 (14)
H18	0.2482	0.5931	0.3377	0.046*
C19	0.2593 (8)	0.62806 (19)	0.4964 (4)	0.0250 (11)
C20	0.2708 (9)	0.6123 (2)	0.6106 (4)	0.0309 (12)
H20	0.2821	0.6416	0.6665	0.037*
C21	0.2661 (9)	0.5562 (2)	0.6441 (4)	0.0328 (13)
H21	0.2727	0.5469	0.7224	0.039*
C22	0.2679 (8)	0.6892 (2)	0.4604 (4)	0.0268 (11)
C23	0.2038 (10)	0.7331 (2)	0.5287 (5)	0.0394 (15)
H23	0.1455	0.7245	0.5990	0.047*
C24	0.2249 (10)	0.7896 (2)	0.4943 (6)	0.0478 (16)
H24	0.1852	0.8188	0.5451	0.057*
C25	0.3562 (10)	0.7637 (2)	0.3315 (5)	0.0415 (15)
H25	0.4118	0.7738	0.2613	0.050*
C26	0.3452 (9)	0.7060 (2)	0.3573 (5)	0.0365 (13)
H26	0.3898	0.6780	0.3054	0.044*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.043 (3)	0.040 (2)	0.038 (2)	−0.0029 (19)	0.004 (2)	−0.0039 (18)
N1	0.079 (4)	0.018 (2)	0.029 (2)	−0.004 (2)	0.003 (3)	−0.0024 (18)
N2	0.058 (3)	0.0164 (19)	0.028 (2)	−0.002 (2)	−0.005 (2)	−0.0011 (16)
N3	0.071 (4)	0.030 (2)	0.045 (3)	−0.003 (3)	−0.005 (3)	0.007 (2)
C1	0.073 (5)	0.012 (2)	0.024 (2)	0.009 (3)	−0.003 (3)	0.0020 (18)
C2	0.054 (4)	0.074 (5)	0.035 (4)	0.005 (4)	0.000 (3)	−0.018 (3)
C3	0.084 (6)	0.053 (4)	0.026 (3)	−0.004 (4)	−0.001 (3)	−0.019 (3)
C4	0.073 (5)	0.038 (3)	0.033 (3)	0.008 (3)	0.006 (3)	0.000 (3)
C5	0.058 (5)	0.069 (5)	0.042 (4)	0.000 (4)	−0.002 (3)	−0.013 (3)
C6	0.047 (4)	0.040 (3)	0.041 (3)	0.002 (3)	0.000 (3)	−0.012 (3)
C7	0.052 (4)	0.019 (2)	0.026 (3)	0.000 (2)	0.001 (3)	0.008 (2)
C8	0.040 (3)	0.024 (2)	0.019 (2)	0.006 (2)	−0.001 (2)	−0.0001 (19)
C9	0.032 (3)	0.022 (2)	0.025 (2)	0.003 (2)	−0.002 (2)	−0.0011 (18)
C10	0.047 (4)	0.032 (3)	0.026 (3)	0.001 (3)	−0.001 (3)	0.006 (2)
C11	0.054 (4)	0.029 (3)	0.032 (3)	−0.006 (3)	0.000 (3)	−0.009 (2)
C12	0.060 (4)	0.018 (2)	0.038 (3)	−0.009 (3)	0.007 (3)	0.003 (2)
C13	0.054 (4)	0.032 (3)	0.028 (3)	−0.004 (3)	−0.002 (3)	0.000 (2)
C14	0.048 (4)	0.037 (3)	0.026 (3)	−0.006 (3)	0.002 (3)	−0.002 (2)
C15	0.084 (5)	0.018 (2)	0.022 (3)	0.007 (3)	0.005 (3)	−0.0030 (19)
C16	0.060 (4)	0.023 (2)	0.022 (2)	0.007 (3)	0.004 (3)	0.0016 (19)
C17	0.100 (6)	0.022 (3)	0.020 (2)	0.003 (3)	0.006 (3)	−0.005 (2)
C18	0.070 (4)	0.023 (2)	0.021 (2)	0.009 (3)	−0.001 (3)	−0.0002 (19)
C19	0.032 (3)	0.018 (2)	0.026 (2)	0.005 (2)	0.002 (2)	−0.0038 (18)
C20	0.047 (4)	0.022 (2)	0.025 (2)	−0.004 (2)	0.004 (3)	−0.0036 (19)
C21	0.052 (4)	0.031 (3)	0.015 (2)	0.002 (3)	−0.005 (3)	0.0019 (19)
C22	0.030 (3)	0.025 (2)	0.025 (2)	0.001 (2)	−0.004 (2)	0.0019 (18)
C23	0.058 (4)	0.030 (3)	0.029 (3)	0.008 (3)	0.009 (3)	0.000 (2)
C24	0.061 (4)	0.031 (3)	0.051 (4)	0.001 (3)	0.002 (4)	−0.011 (3)
C25	0.055 (4)	0.033 (3)	0.037 (3)	0.000 (3)	0.011 (3)	0.007 (2)
C26	0.043 (3)	0.035 (3)	0.031 (3)	0.003 (3)	0.007 (3)	0.005 (2)

Geometric parameters (Å, º) top

O1—C7	1.217 (7)	C12—C13	1.370 (8)
N1—C8	1.255 (7)	C12—H12	0.95
N1—N2	1.425 (6)	C13—C14	1.374 (8)
N2—C15	1.271 (7)	C13—H13	0.95
N3—C24	1.318 (8)	C14—H14	0.95
N3—C25	1.325 (8)	C15—C16	1.455 (7)
C1—C2	1.39	C15—H15	0.95
C1—C6	1.39	C16—C21	1.397 (7)
C1—C7	1.463 (6)	C16—C17	1.392 (7)
C2—C3	1.39	C17—C18	1.378 (7)
C2—H2	0.95	C17—H17	0.95
C3—C4	1.39	C18—C19	1.400 (7)
C3—H3	0.95	C18—H18	0.95
C4—C5	1.39	C19—C20	1.399 (7)
C4—H4	0.95	C19—C22	1.487 (6)
C5—C6	1.39	C20—C21	1.366 (7)
C5—H5	0.95	C20—H20	0.95
C6—H6	0.95	C21—H21	0.95
C7—C8	1.544 (8)	C22—C23	1.379 (7)
C8—C9	1.490 (7)	C22—C26	1.394 (7)
C9—C10	1.384 (7)	C23—C24	1.387 (8)
C9—C14	1.399 (7)	C23—H23	0.95
C10—C11	1.399 (8)	C24—H24	0.95
C10—H10	0.95	C25—C26	1.378 (8)
C11—C12	1.389 (8)	C25—H25	0.95
C11—H11	0.95	C26—H26	0.95

C8—N1—N2	113.1 (4)	C14—C13—H13	119.9
C15—N2—N1	111.3 (4)	C13—C14—C9	120.1 (5)
C24—N3—C25	114.6 (5)	C13—C14—H14	119.9
C2—C1—C6	120.0	C9—C14—H14	119.9
C2—C1—C7	119.8 (4)	N2—C15—C16	123.8 (5)
C6—C1—C7	120.1 (4)	N2—C15—H15	118.1
C1—C2—C3	120.0	C16—C15—H15	118.1
C1—C2—H2	120.0	C21—C16—C17	118.7 (4)
C3—C2—H2	120.0	C21—C16—C15	122.5 (4)
C4—C3—C2	120.0	C17—C16—C15	118.7 (5)
C4—C3—H3	120.0	C18—C17—C16	120.8 (5)
C2—C3—H3	120.0	C18—C17—H17	119.6
C5—C4—C3	120.0	C16—C17—H17	119.6
C5—C4—H4	120.0	C17—C18—C19	120.8 (5)
C3—C4—H4	120.0	C17—C18—H18	119.6
C4—C5—C6	120.0	C19—C18—H18	119.6
C4—C5—H5	120.0	C20—C19—C18	117.6 (4)
C6—C5—H5	120.0	C20—C19—C22	121.5 (4)
C5—C6—C1	120.0	C18—C19—C22	120.8 (4)
C5—C6—H6	120.0	C21—C20—C19	121.8 (4)
C1—C6—H6	120.0	C21—C20—H20	119.1
O1—C7—C1	121.7 (5)	C19—C20—H20	119.1
O1—C7—C8	119.2 (5)	C20—C21—C16	120.2 (4)
C1—C7—C8	119.1 (5)	C20—C21—H21	119.9
N1—C8—C9	119.8 (4)	C16—C21—H21	119.9
N1—C8—C7	121.5 (4)	C23—C22—C26	115.9 (5)
C9—C8—C7	117.9 (4)	C23—C22—C19	121.8 (4)
C10—C9—C14	119.7 (5)	C26—C22—C19	122.3 (5)
C10—C9—C8	119.2 (4)	C22—C23—C24	119.6 (5)
C14—C9—C8	121.1 (5)	C22—C23—H23	120.2
C11—C10—C9	119.8 (5)	C24—C23—H23	120.2
C11—C10—H10	120.1	N3—C24—C23	125.1 (6)
C9—C10—H10	120.1	N3—C24—H24	117.4
C10—C11—C12	119.1 (5)	C23—C24—H24	117.4
C10—C11—H11	120.4	N3—C25—C26	125.4 (5)
C12—C11—H11	120.4	N3—C25—H25	117.3
C13—C12—C11	120.9 (5)	C26—C25—H25	117.3
C13—C12—H12	119.6	C25—C26—C22	119.2 (5)
C11—C12—H12	119.6	C25—C26—H26	120.4
C12—C13—C14	120.1 (5)	C22—C26—H26	120.4
C12—C13—H13	119.9

C8—N1—N2—C15	162.2 (6)	C12—C13—C14—C9	2.1 (9)
C6—C1—C2—C3	0.0	C10—C9—C14—C13	2.5 (9)
C7—C1—C2—C3	178.9 (4)	C8—C9—C14—C13	−177.5 (5)
C1—C2—C3—C4	0.0	N1—N2—C15—C16	177.4 (6)
C2—C3—C4—C5	0.0	N2—C15—C16—C21	−6.3 (11)
C3—C4—C5—C6	0.0	N2—C15—C16—C17	178.1 (7)
C4—C5—C6—C1	0.0	C21—C16—C17—C18	−0.7 (11)
C2—C1—C6—C5	0.0	C15—C16—C17—C18	175.0 (7)
C7—C1—C6—C5	−178.9 (4)	C16—C17—C18—C19	−1.2 (11)
C2—C1—C7—O1	−5.1 (6)	C17—C18—C19—C20	2.8 (10)
C6—C1—C7—O1	173.8 (4)	C17—C18—C19—C22	179.1 (6)
C2—C1—C7—C8	173.7 (3)	C18—C19—C20—C21	−2.6 (9)
C6—C1—C7—C8	−7.5 (6)	C22—C19—C20—C21	−178.9 (5)
N2—N1—C8—C9	−178.8 (5)	C19—C20—C21—C16	0.7 (10)
N2—N1—C8—C7	−9.0 (8)	C17—C16—C21—C20	0.9 (10)
O1—C7—C8—N1	−84.7 (7)	C15—C16—C21—C20	−174.6 (6)
C1—C7—C8—N1	96.5 (6)	C20—C19—C22—C23	−29.9 (9)
O1—C7—C8—C9	85.3 (6)	C18—C19—C22—C23	153.9 (6)
C1—C7—C8—C9	−93.5 (6)	C20—C19—C22—C26	148.4 (6)
N1—C8—C9—C10	0.1 (8)	C18—C19—C22—C26	−27.8 (9)
C7—C8—C9—C10	−170.0 (5)	C26—C22—C23—C24	−2.2 (9)
N1—C8—C9—C14	−179.9 (6)	C19—C22—C23—C24	176.3 (6)
C7—C8—C9—C14	10.0 (8)	C25—N3—C24—C23	−2.9 (11)
C14—C9—C10—C11	−4.3 (9)	C22—C23—C24—N3	3.2 (11)
C8—C9—C10—C11	175.7 (5)	C24—N3—C25—C26	1.9 (10)
C9—C10—C11—C12	1.6 (9)	N3—C25—C26—C22	−1.2 (10)
C10—C11—C12—C13	3.0 (10)	C23—C22—C26—C25	1.3 (9)
C11—C12—C13—C14	−4.9 (10)	C19—C22—C26—C25	−177.2 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C26—H26···O1ⁱ	0.95	2.57	3.502 (7)	166

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₆H₁₉N₃O
M_r	389.44
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	140
a, b, c (Å)	7.1182 (2), 23.2745 (7), 11.8040 (4)
β (°)	90.278 (2)
V (Å³)	1955.6 (1)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.45 × 0.15 × 0.05

Data collection
Diffractometer	Bruker SMART APEX area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	11057, 3433, 2825
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.093, 0.252, 1.08
No. of reflections	3433
No. of parameters	260
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.63, −0.38

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C26—H26···O1ⁱ	0.95	2.57	3.502 (7)	166

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

The authors thank Vijaygarh Jyotish Ray College and the University of Malaya for supporting this study.

References

Abbasi, A., Mohammadi Ziarani, G. & Tarighi, S. (2007). Acta Cryst. E63, o2579–o2580. Web of Science CSD CrossRef IUCr Journals Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chowdhury, S., Drew, M. G. B. & Datta, D. (2003). Inorg. Chem. Commun. 6, 1014–1016. Web of Science CSD CrossRef CAS Google Scholar
Liu, Q.-K., Ma, J.-P., Huang, R.-Q. & Dong, Y.-B. (2007). Acta Cryst. E63, o2646–o2647. Web of Science CSD CrossRef IUCr Journals Google Scholar
Schweizer, E. E., Hayes, J. E., Lee, K. J. & Rheingold, A. L. (1987). J. Org. Chem. 52, 1324–1332. CSD CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar