1-(3-Meth­oxy­phen­yl)-4,5-dimethyl-2-phenyl-1H-imidazole

Rizwana Begum, S.; Hema, R.; Srinivasan, N.; Anitha, A.G.

doi:10.1107/S1600536813016966

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 7| July 2013| Page o1154

https://doi.org/10.1107/S1600536813016966

Open

access

1-(3-Methoxyphenyl)-4,5-dimethyl-2-phenyl-1H-imidazole

S. Rizwana Begum,^a R. Hema,^a ^* N. Srinivasan ^b and A. G. Anitha ^a

^aDepartment of Physics, Seethalakshmi Ramaswami College (Autonomous), Tiruchirappalli 620 002, India, and ^bDepartment of Chemistry, S.K.P. Engineering College, Thiruvanamalai 606 611, India
^*Correspondence e-mail: raghema2000@yahoo.co.in

(Received 8 June 2013; accepted 19 June 2013; online 26 June 2013)

In the title compound, C₁₈H₁₈N₂O, the imidazole ring makes dihedral angles of 68.26 (7) and 22.45 (9)° with the methoxyphenyl and phenyl rings, respectively. The dihedral angle between the methoxyphenyl and phenyl ring is 71.86 (7)°. In the crystal, weak intermolecular C—H⋯O and C—H⋯N hydrogen bonds link the molecules into columns propagated in [101].

Related literature

For related structures, see: Gayathri et al. (2010 ); Rosepriya et al. (2011 ). For graph-set motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₈H₁₈N₂O
M_r = 278.34
Triclinic, $[P \overline 1]$
a = 8.0199 (1) Å
b = 9.4807 (1) Å
c = 10.4971 (2) Å
α = 108.339 (1)°
β = 94.910 (1)°
γ = 90.535 (1)°
V = 754.27 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.35 × 0.30 × 0.30 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.974, T_max = 0.977
14252 measured reflections
2644 independent reflections
2159 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.148
S = 1.04
2644 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯O1ⁱ	0.96	2.57	3.316 (3)	135
C7—H7⋯N2ⁱⁱ	0.93	2.58	3.493 (2)	168
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 (Farrugia, 2012 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536813016966/cv5418sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813016966/cv5418Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813016966/cv5418Isup3.cml

checkCIF report

Comment top

In a continuation of structural studies of 4,5-dimethyl-1H-imidazole derivatives (Gayathri et al., 2010; Rosepriya et al., 2011), herewith we present the title compound, (I).

In (I) (Fig. 1), the imidazole ring is essentially planar [maximum deviation of 0.0036 (11) Å for N2 and -0.0036 (11) Å N1]. The imidazole ring makes dihedral angle of 68.26 (7)° and 22.45 (9)° with the methoxyphenyl (C6–C11) and phenyl (C13–C18) rings, respectively. The dihedral angle between the methoxyphenyl and phenyl rings is 71.86 (7)°.

The crystal structure is stabilized by weak C—H···O and C—H···N intermolecular interactions (Table 1). The C—H···O interactions link pairs of molecules across centres of inversion to give the ring motif R(16) (Bernstein et al., 1995). Atom C7 acts as a donor for a weak intermolecular C—H···N interaction via H7 with the nitrogen atom in the imidazole moiety, thus forming extended chains with a graph set motif C(6) (Bernstein et al., 1995).

Related literature top

For related structures, see: Gayathri et al. (2010); Rosepriya et al. (2011). For graph-set motifs, see: Bernstein et al. (1995).

Experimental top

To pure butane-2,3-dione (1.48 g, 15 mmol) in ethanol (10 ml), m-methoxy aniline (1.5 g, 15 mmol), ammonium acetate (1.15 g, 15 mmol) and benzaldehyde (1.5 g, 15 mmol) was added about 1 h by maintaining the temperature at 333 K. The reaction mixture was refluxed for 7 days and extracted with dichloromethane. The solid separated was purified by column chromatography using hexane: ethyl acetate as the eluent. Yield: 1.91 g (46%).

Structure description top

In a continuation of structural studies of 4,5-dimethyl-1H-imidazole derivatives (Gayathri et al., 2010; Rosepriya et al., 2011), herewith we present the title compound, (I).

For related structures, see: Gayathri et al. (2010); Rosepriya et al. (2011). For graph-set motifs, see: Bernstein et al. (1995).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound,showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented by circles of arbitrary radii.

1-(3-Methoxyphenyl)-4,5-dimethyl-2-phenyl-1H-imidazole top

Crystal data top

C₁₈H₁₈N₂O	Z = 2
M_r = 278.34	F(000) = 296
Triclinic, P1	D_x = 1.226 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0199 (1) Å	Cell parameters from 2644 reflections
b = 9.4807 (1) Å	θ = 2.3–30.6°
c = 10.4971 (2) Å	µ = 0.08 mm⁻¹
α = 108.339 (1)°	T = 293 K
β = 94.910 (1)°	Block, colourless
γ = 90.535 (1)°	0.35 × 0.30 × 0.30 mm
V = 754.27 (2) Å³

Data collection top

Bruker Kappa APEXII CCD diffractometer	2644 independent reflections
Radiation source: fine-focus sealed tube	2159 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ω and φ scan	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −9→9
T_min = 0.974, T_max = 0.977	k = −11→11
14252 measured reflections	l = −12→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)] = 0.046	H-atom parameters constrained
wR(F²) = 0.148	w = 1/[σ²(F_o²) + (0.0747P)² + 0.2805P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
2644 reflections	Δρ_max = 0.33 e Å⁻³
191 parameters	Δρ_min = −0.22 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.028 (7)

Crystal data top

C₁₈H₁₈N₂O	γ = 90.535 (1)°
M_r = 278.34	V = 754.27 (2) Å³
Triclinic, P1	Z = 2
a = 8.0199 (1) Å	Mo Kα radiation
b = 9.4807 (1) Å	µ = 0.08 mm⁻¹
c = 10.4971 (2) Å	T = 293 K
α = 108.339 (1)°	0.35 × 0.30 × 0.30 mm
β = 94.910 (1)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	2644 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	2159 reflections with I > 2σ(I)
T_min = 0.974, T_max = 0.977	R_int = 0.021
14252 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.148	H-atom parameters constrained
S = 1.04	Δρ_max = 0.33 e Å⁻³
2644 reflections	Δρ_min = −0.22 e Å⁻³
191 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
C1	0.7362 (2)	0.4690 (2)	−0.02515 (17)	0.0442 (4)
C2	0.7291 (3)	0.7075 (2)	0.05116 (19)	0.0521 (5)
C3	0.7842 (3)	0.6639 (2)	0.15818 (19)	0.0513 (5)
C4	0.6975 (4)	0.8605 (2)	0.0466 (3)	0.0792 (7)
H4A	0.6594	0.8561	−0.0438	0.119*
H4B	0.7993	0.9205	0.0751	0.119*
H4C	0.6135	0.9036	0.1057	0.119*
C5	0.8313 (3)	0.7516 (3)	0.3018 (2)	0.0713 (7)
H5A	0.8654	0.6856	0.3514	0.107*
H5B	0.7368	0.8053	0.3393	0.107*
H5C	0.9222	0.8206	0.3072	0.107*
C6	0.8135 (2)	0.4174 (2)	0.19308 (17)	0.0440 (4)
C7	0.6791 (2)	0.3354 (2)	0.21018 (19)	0.0500 (5)
H7	0.5731	0.3408	0.1689	0.060*
C8	0.7059 (3)	0.2451 (2)	0.2900 (2)	0.0569 (5)
H8	0.6170	0.1879	0.3015	0.068*
C9	0.8613 (3)	0.2385 (2)	0.3528 (2)	0.0557 (5)
H9	0.8773	0.1770	0.4061	0.067*
C10	0.9949 (2)	0.3234 (2)	0.33671 (17)	0.0483 (5)
C11	0.9717 (2)	0.4125 (2)	0.25552 (17)	0.0466 (5)
H11	1.0610	0.4685	0.2429	0.056*
C12	1.2812 (3)	0.4015 (3)	0.3979 (2)	0.0701 (6)
H12A	1.3781	0.3800	0.4479	0.105*
H12B	1.2553	0.5040	0.4365	0.105*
H12C	1.3037	0.3830	0.3058	0.105*
C13	0.7294 (2)	0.3179 (2)	−0.12117 (18)	0.0482 (5)
C14	0.8223 (3)	0.2026 (2)	−0.1019 (2)	0.0621 (6)
H14	0.8895	0.2175	−0.0217	0.075*
C15	0.8159 (3)	0.0654 (3)	−0.2010 (3)	0.0743 (7)
H15	0.8778	−0.0114	−0.1864	0.089*
C16	0.7189 (4)	0.0416 (3)	−0.3206 (3)	0.0770 (7)
H16	0.7157	−0.0505	−0.3872	0.092*
C17	0.6270 (3)	0.1548 (3)	−0.3408 (2)	0.0765 (7)
H17	0.5617	0.1395	−0.4219	0.092*
C18	0.6304 (3)	0.2911 (2)	−0.2422 (2)	0.0611 (6)
H18	0.5654	0.3663	−0.2568	0.073*
N1	0.78868 (18)	0.51065 (17)	0.10977 (14)	0.0450 (4)
N2	0.70075 (19)	0.58661 (17)	−0.06211 (15)	0.0489 (4)
O1	1.14352 (18)	0.30952 (17)	0.40312 (15)	0.0643 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0460 (9)	0.0516 (11)	0.0371 (9)	0.0035 (7)	0.0034 (7)	0.0172 (8)
C2	0.0646 (12)	0.0465 (11)	0.0461 (11)	−0.0015 (8)	−0.0005 (8)	0.0172 (9)
C3	0.0627 (12)	0.0481 (11)	0.0416 (10)	−0.0036 (8)	−0.0016 (8)	0.0140 (8)
C4	0.119 (2)	0.0510 (13)	0.0667 (15)	−0.0024 (13)	−0.0097 (14)	0.0222 (11)
C5	0.1036 (18)	0.0594 (13)	0.0453 (12)	−0.0065 (12)	−0.0068 (11)	0.0125 (10)
C6	0.0527 (10)	0.0467 (10)	0.0339 (9)	0.0052 (8)	0.0062 (7)	0.0141 (8)
C7	0.0503 (10)	0.0528 (11)	0.0474 (10)	0.0035 (8)	0.0058 (8)	0.0163 (9)
C8	0.0627 (12)	0.0527 (12)	0.0594 (12)	−0.0002 (9)	0.0132 (9)	0.0217 (10)
C9	0.0733 (13)	0.0490 (11)	0.0520 (11)	0.0099 (9)	0.0110 (9)	0.0246 (9)
C10	0.0579 (11)	0.0516 (11)	0.0357 (9)	0.0134 (8)	0.0049 (8)	0.0136 (8)
C11	0.0499 (10)	0.0529 (11)	0.0395 (9)	0.0028 (8)	0.0061 (7)	0.0175 (8)
C12	0.0587 (13)	0.0918 (17)	0.0619 (14)	0.0079 (11)	−0.0043 (10)	0.0295 (13)
C13	0.0544 (10)	0.0507 (11)	0.0417 (10)	0.0035 (8)	0.0101 (8)	0.0162 (9)
C14	0.0744 (14)	0.0645 (14)	0.0477 (11)	0.0183 (11)	0.0104 (10)	0.0166 (10)
C15	0.0971 (18)	0.0581 (14)	0.0686 (15)	0.0237 (12)	0.0217 (13)	0.0173 (12)
C16	0.1025 (19)	0.0565 (14)	0.0621 (15)	0.0029 (12)	0.0126 (13)	0.0031 (11)
C17	0.0965 (18)	0.0652 (15)	0.0556 (14)	−0.0038 (13)	−0.0093 (12)	0.0061 (11)
C18	0.0733 (14)	0.0555 (12)	0.0511 (12)	0.0024 (10)	−0.0042 (10)	0.0147 (10)
N1	0.0508 (9)	0.0488 (9)	0.0371 (8)	0.0020 (6)	0.0013 (6)	0.0165 (7)
N2	0.0566 (9)	0.0512 (9)	0.0410 (8)	0.0011 (7)	0.0000 (7)	0.0189 (7)
O1	0.0634 (9)	0.0770 (10)	0.0610 (9)	0.0117 (7)	−0.0025 (7)	0.0360 (8)

Geometric parameters (Å, º) top

C1—N2	1.317 (2)	C9—C10	1.386 (3)
C1—N1	1.372 (2)	C9—H9	0.9300
C1—C13	1.467 (3)	C10—O1	1.358 (2)
C2—C3	1.356 (3)	C10—C11	1.380 (3)
C2—N2	1.368 (2)	C11—H11	0.9300
C2—C4	1.490 (3)	C12—O1	1.416 (3)
C3—N1	1.382 (2)	C12—H12A	0.9600
C3—C5	1.488 (3)	C12—H12B	0.9600
C4—H4A	0.9600	C12—H12C	0.9600
C4—H4B	0.9600	C13—C14	1.386 (3)
C4—H4C	0.9600	C13—C18	1.389 (3)
C5—H5A	0.9600	C14—C15	1.383 (3)
C5—H5B	0.9600	C14—H14	0.9300
C5—H5C	0.9600	C15—C16	1.373 (4)
C6—C7	1.380 (3)	C15—H15	0.9300
C6—C11	1.385 (2)	C16—C17	1.368 (4)
C6—N1	1.431 (2)	C16—H16	0.9300
C7—C8	1.380 (3)	C17—C18	1.377 (3)
C7—H7	0.9300	C17—H17	0.9300
C8—C9	1.371 (3)	C18—H18	0.9300
C8—H8	0.9300

N2—C1—N1	110.51 (16)	O1—C10—C9	115.68 (17)
N2—C1—C13	122.63 (16)	C11—C10—C9	119.90 (17)
N1—C1—C13	126.73 (16)	C10—C11—C6	119.00 (17)
C3—C2—N2	110.20 (17)	C10—C11—H11	120.5
C3—C2—C4	128.78 (19)	C6—C11—H11	120.5
N2—C2—C4	121.02 (17)	O1—C12—H12A	109.5
C2—C3—N1	105.96 (16)	O1—C12—H12B	109.5
C2—C3—C5	130.95 (19)	H12A—C12—H12B	109.5
N1—C3—C5	123.08 (17)	O1—C12—H12C	109.5
C2—C4—H4A	109.5	H12A—C12—H12C	109.5
C2—C4—H4B	109.5	H12B—C12—H12C	109.5
H4A—C4—H4B	109.5	C14—C13—C18	117.98 (19)
C2—C4—H4C	109.5	C14—C13—C1	124.16 (18)
H4A—C4—H4C	109.5	C18—C13—C1	117.77 (17)
H4B—C4—H4C	109.5	C15—C14—C13	120.5 (2)
C3—C5—H5A	109.5	C15—C14—H14	119.7
C3—C5—H5B	109.5	C13—C14—H14	119.7
H5A—C5—H5B	109.5	C16—C15—C14	120.6 (2)
C3—C5—H5C	109.5	C16—C15—H15	119.7
H5A—C5—H5C	109.5	C14—C15—H15	119.7
H5B—C5—H5C	109.5	C17—C16—C15	119.3 (2)
C7—C6—C11	121.60 (17)	C17—C16—H16	120.3
C7—C6—N1	119.22 (16)	C15—C16—H16	120.3
C11—C6—N1	119.18 (16)	C16—C17—C18	120.6 (2)
C6—C7—C8	118.36 (18)	C16—C17—H17	119.7
C6—C7—H7	120.8	C18—C17—H17	119.7
C8—C7—H7	120.8	C17—C18—C13	120.9 (2)
C9—C8—C7	121.02 (19)	C17—C18—H18	119.5
C9—C8—H8	119.5	C13—C18—H18	119.5
C7—C8—H8	119.5	C1—N1—C3	106.80 (15)
C8—C9—C10	120.11 (18)	C1—N1—C6	127.92 (15)
C8—C9—H9	119.9	C3—N1—C6	124.33 (15)
C10—C9—H9	119.9	C1—N2—C2	106.53 (15)
O1—C10—C11	124.41 (18)	C10—O1—C12	117.98 (16)

N2—C2—C3—N1	−0.6 (2)	C15—C16—C17—C18	−0.4 (4)
C4—C2—C3—N1	178.6 (2)	C16—C17—C18—C13	1.3 (4)
N2—C2—C3—C5	−179.7 (2)	C14—C13—C18—C17	−1.1 (3)
C4—C2—C3—C5	−0.5 (4)	C1—C13—C18—C17	175.5 (2)
C11—C6—C7—C8	−1.0 (3)	N2—C1—N1—C3	0.2 (2)
N1—C6—C7—C8	179.48 (16)	C13—C1—N1—C3	176.15 (17)
C6—C7—C8—C9	1.0 (3)	N2—C1—N1—C6	169.31 (16)
C7—C8—C9—C10	0.1 (3)	C13—C1—N1—C6	−14.8 (3)
C8—C9—C10—O1	179.81 (17)	C2—C3—N1—C1	0.2 (2)
C8—C9—C10—C11	−1.2 (3)	C5—C3—N1—C1	179.5 (2)
O1—C10—C11—C6	−179.95 (16)	C2—C3—N1—C6	−169.35 (17)
C9—C10—C11—C6	1.1 (3)	C5—C3—N1—C6	9.9 (3)
C7—C6—C11—C10	0.0 (3)	C7—C6—N1—C1	−61.6 (2)
N1—C6—C11—C10	179.45 (15)	C11—C6—N1—C1	118.9 (2)
N2—C1—C13—C14	153.96 (19)	C7—C6—N1—C3	105.7 (2)
N1—C1—C13—C14	−21.5 (3)	C11—C6—N1—C3	−73.8 (2)
N2—C1—C13—C18	−22.4 (3)	N1—C1—N2—C2	−0.6 (2)
N1—C1—C13—C18	162.10 (19)	C13—C1—N2—C2	−176.70 (16)
C18—C13—C14—C15	0.1 (3)	C3—C2—N2—C1	0.7 (2)
C1—C13—C14—C15	−176.29 (19)	C4—C2—N2—C1	−178.6 (2)
C13—C14—C15—C16	0.7 (4)	C11—C10—O1—C12	5.4 (3)
C14—C15—C16—C17	−0.6 (4)	C9—C10—O1—C12	−175.63 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···O1ⁱ	0.96	2.57	3.316 (3)	135
C7—H7···N2ⁱⁱ	0.93	2.58	3.493 (2)	168

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₈N₂O
M_r	278.34
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.0199 (1), 9.4807 (1), 10.4971 (2)
α, β, γ (°)	108.339 (1), 94.910 (1), 90.535 (1)
V (Å³)	754.27 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.35 × 0.30 × 0.30

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.974, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	14252, 2644, 2159
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.148, 1.04
No. of reflections	2644
No. of parameters	191
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.22

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···O1ⁱ	0.96	2.57	3.316 (3)	135
C7—H7···N2ⁱⁱ	0.93	2.58	3.493 (2)	168

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

Acknowledgements

The authors are grateful to the SAIF, IIT Madras, for the data collection.

References

Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. CrossRef Web of Science IUCr Journals Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Gayathri, P., Jayabharathi, J., Srinivasan, N., Thiruvalluvar, A. & Butcher, R. J. (2010). Acta Cryst. E66, o1703. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rosepriya, S., Thiruvalluvar, A., Jayabharathi, J., Srinivasan, N., Butcher, R. J., Jasinski, J. P. & Golen, J. A. (2011). Acta Cryst. E67, o1065. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar