3-(4-Chloro­phen­yl)-5-phenyl-4,5-di­hydro-1,3-oxazole

Islor, A.M.; Yaradoni, R.; Garudachari, B.; Gerber, T.; Hosten, E.; Betz, R.

doi:10.1107/S1600536812043711

organic compounds

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page o3215

doi:10.1107/S1600536812043711

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3-(4-Chlorophenyl)-5-phenyl-4,5-dihydro-1,3-oxazole

Arun M. Islor,^a Rajiv Yaradoni,^a B. Garudachari,^a Thomas Gerber,^b Eric Hosten ^b and Richard Betz ^b ^*

^aNational Institute of Technology-Karnataka, Department of Chemistry, Medicinal Chemistry Laboratory, Surathkal, Mangalore 575 025, India, and ^bNelson Mandela Metropolitan University, Summerstrand Campus, Department of Chemistry, University Way, Summerstrand, PO Box 77000, Port Elizabeth, 6031, South Africa
^*Correspondence e-mail: richard.betz@webmail.co.za

(Received 9 October 2012; accepted 22 October 2012; online 27 October 2012)

In the title compound, C₁₅H₁₂ClNO, the isoxazoline ring adopts an envelope conformation with the C atom bearing an unsubstituted phenyl ring as the flap atom. The chlorinated phenyl group is nearly in-plane with the four coplanar atoms of the heterocycle and the corresponding mean planes enclosing an angle of 1.16 (7)°. The unsubstituted phenyl group attached to the envelope flap atom approaches a nearly perpendicular orientation relative to the isoxazoline ring with a dihedral angle of 74.93 (7)°. In the crystal, weak C—H⋯O, C—H⋯N and C—H⋯π interactions connect the molecules into layers perpendicular to the a axis.

Related literature

For the biological and medicinal importance of isoxazole compounds, see: Miller et al. (2009 ); Prasad et al. (2007 ). For their use in ring-opening polymerizations, see: Wiesbrock et al. (2005 ). For the puckering analysis of five-membered rings, see: Cremer & Pople (1975 ). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ); Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₅H₁₂ClNO
M_r = 257.71
Monoclinic, C 2/c
a = 29.797 (5) Å
b = 10.717 (5) Å
c = 8.086 (5) Å
β = 103.088 (5)°
V = 2515 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 200 K
0.58 × 0.42 × 0.21 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.850, T_max = 0.943
11843 measured reflections
3132 independent reflections
2637 reflections with I > 2σ(I)
R_int = 0.014

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.103
S = 1.03
3132 reflections
163 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C11–C16 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯N1ⁱ	0.95	2.74	3.657 (2)	163
C12—H12⋯O1ⁱ	0.95	2.65	3.390 (2)	135
C2—H2B⋯O1ⁱⁱ	0.99	2.67	3.466 (2)	138
C26—H26⋯O1ⁱⁱ	0.95	2.70	3.431 (2)	134
C22—H22⋯Cgⁱⁱⁱ	0.95	2.81	3.721 (3)	162
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x, -y, z-{\script{1\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

Data collection: APEX2 (Bruker, 2010 ); cell refinement: SAINT (Bruker, 2010); 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 Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812043711/gk2526sup1.cif

Supporting information file. DOI: 10.1107/S1600536812043711/gk2526Isup2.cdx

Structure factors: contains datablock I. DOI: 10.1107/S1600536812043711/gk2526Isup3.hkl

Supporting information file. DOI: 10.1107/S1600536812043711/gk2526Isup4.cml

checkCIF report

Comment top

Isoxazoles are well known organic compounds which are included in a variety of complex biologically active structures and play a role as catalyst, ligands and intermediates for functional compounds (Miller et al., 2009; Prasad et al., 2007). Isoxazoles appear in numerous medicinally active compounds and natural products of biological significance. Additionally, they are valuable as synthetic intermediates or protecting groups in organic synthesis. Also, isoxazoles serve as monomers for the synthesis of substituted poly(imine)s by cationic ring-opening polymerization (Wiesbrock et al., 2005). Due to our interest in developing new isoxazole-based heterocycles, we have synthesized the title compound to study its crystal structure.

The title molecule features a chlorinated as well as a non-halogenated phenyl group as substituents on a central isoxazole core. The latter one adopts a ⁵E conformation with the flap atom on C3 (Cremer & Pople, 1975). While the halogenated phenyl group is nearly in-plane with the isoxazoline moiety – the least-squares planes defined by the respective intracyclic atoms intersect at an angle of 7.16 (7) ° only – the non-substituted phenyl group adopts a nearly perpendicular orientation towards the isoxazole moiety. The corresponding least-squares planes in the latter case enclose an angle of 74.93 (7) ° (Fig. 1).

In the crystal, only weak C–H···O and C–H···N contacts whose range falls slightly below the sum of van-der-Waals radii of the atoms participating in them are observed. The hydrogen atom that is part of the C–H···N contact stems from the chlorinated phenyl substituent and is also the origin of a bifuracated hydrogen bond that extends to the oxygen atom as acceptor. The C–H···O contacts are supported by the intracyclic methylene group as well as a hydrogen atom on the non-substituted phenyl group. Taking into account the latter two findings, the oxygen atom acts as threefold acceptor. Metrical parameters as well as information about the symmetry codes for these contacts are summarized in Table 1. In total, the molecules are connected to layers perpendicular to the crystallographic a axis. In terms of graph-set analysis (Etter et al., 1990; Bernstein et al., 1995), the descriptor for these contacts is C¹₁(4)C¹₁(5)C¹₁(5)C¹₁(6) on the unary level. The shortest intercentroid distance between two aromatic systems was measured at 4.709 (3) Å and is observed between the halogenated phenyl group and its symmetry-generated equivalent (Fig. 2).

The packing of the title compound in the crystal structure is shown in Figure 3.

Related literature top

For the biological and medicinal importance of isoxazole compounds, see: Miller et al. (2009); Prasad et al. (2007). For their use in ring-opening polymerizations, see: Wiesbrock et al. (2005). For the puckering analysis of five-membered rings, see: Cremer & Pople (1975). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990); Bernstein et al. (1995).

Experimental top

An equimolar mixture of 1-(4-chlorophenyl)-N-hydroxymethanimine (0.5 g, 0.0032 mol), N-chloro succinamide (0.58 g, 0.0032 mol) and sodium bicarbonate (0.537 g, 0,0064 mol) in dichloromethane (10 ml) and water (10 ml) was stirred at 0 °C for 1 h. Styrene (0.366 g, 0.0035 mol) was then added to the reaction mixture and stirring was continued for another 12 h at room temperature. After completion of the reaction, the reaction mixture was concentrated and purified by column chromatography using petrol ether and ethyl acetate (v/v = 1:1) as the eluent to afford the title compound as a white solid, yield: 0.63 g (76.8%) (ChemSpider ID: 10496235).

Computing details top

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); 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 Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with anisotropic displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Intermolecular contacts, viewed approximately along [0 - 1 -1]. Symmetry operators: ⁱ x, -y, z + 1/2; ⁱⁱ -x + 1/2, y + 1/2, -z + 1/2.
	Fig. 3. Molecular packing of the title compound, viewed along [0 1 0] (anisotropic displacement ellipsoids drawn at 50% probability level).

3-(4-Chlorophenyl)-5-phenyl-4,5-dihydro-1,3-oxazole top

Crystal data top

C₁₅H₁₂ClNO	F(000) = 1072
M_r = 257.71	D_x = 1.361 Mg m⁻³
Monoclinic, C2/c	Melting point = 406–408 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71069 Å
a = 29.797 (5) Å	Cell parameters from 7100 reflections
b = 10.717 (5) Å	θ = 2.8–28.3°
c = 8.086 (5) Å	µ = 0.29 mm⁻¹
β = 103.088 (5)°	T = 200 K
V = 2515 (2) Å³	Block, colourless
Z = 8	0.58 × 0.42 × 0.21 mm

Data collection top

Bruker APEXII CCD diffractometer	3132 independent reflections
Radiation source: fine-focus sealed tube	2637 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.014
ϕ and ω scans	θ_max = 28.3°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −39→39
T_min = 0.850, T_max = 0.943	k = −14→13
11843 measured reflections	l = −10→9

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.103	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0463P)² + 1.7436P] where P = (F_o² + 2F_c²)/3
3132 reflections	(Δ/σ)_max < 0.001
163 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₅H₁₂ClNO	V = 2515 (2) Å³
M_r = 257.71	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 29.797 (5) Å	µ = 0.29 mm⁻¹
b = 10.717 (5) Å	T = 200 K
c = 8.086 (5) Å	0.58 × 0.42 × 0.21 mm
β = 103.088 (5)°

Data collection top

Bruker APEXII CCD diffractometer	3132 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	2637 reflections with I > 2σ(I)
T_min = 0.850, T_max = 0.943	R_int = 0.014
11843 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.103	H-atom parameters constrained
S = 1.03	Δρ_max = 0.31 e Å⁻³
3132 reflections	Δρ_min = −0.23 e Å⁻³
163 parameters

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

	x	y	z	U_iso*/U_eq
Cl1	0.047465 (13)	0.13436 (5)	−0.07319 (6)	0.06357 (16)
O1	0.30314 (3)	0.00728 (10)	0.48581 (13)	0.0473 (3)
N1	0.25598 (4)	−0.00421 (12)	0.40628 (16)	0.0450 (3)
C1	0.24324 (4)	0.09115 (11)	0.31161 (15)	0.0300 (2)
C2	0.28171 (4)	0.18052 (11)	0.30834 (17)	0.0349 (3)
H2A	0.2724	0.2680	0.3214	0.042*
H2B	0.2931	0.1724	0.2029	0.042*
C3	0.31733 (5)	0.13540 (12)	0.46363 (16)	0.0373 (3)
H3	0.3141	0.1857	0.5645	0.045*
C11	0.19537 (4)	0.10199 (11)	0.21455 (15)	0.0295 (2)
C12	0.18093 (4)	0.20517 (12)	0.11130 (16)	0.0346 (3)
H12	0.2025	0.2686	0.1017	0.042*
C13	0.13540 (5)	0.21625 (13)	0.02230 (17)	0.0405 (3)
H13	0.1256	0.2869	−0.0475	0.049*
C14	0.10459 (4)	0.12302 (13)	0.03681 (17)	0.0389 (3)
C15	0.11790 (4)	0.01975 (13)	0.13904 (17)	0.0388 (3)
H15	0.0962	−0.0432	0.1484	0.047*
C16	0.16323 (4)	0.00951 (12)	0.22721 (17)	0.0354 (3)
H16	0.1727	−0.0612	0.2973	0.043*
C21	0.36712 (4)	0.13532 (11)	0.45344 (15)	0.0321 (3)
C22	0.39722 (5)	0.22193 (12)	0.54584 (18)	0.0409 (3)
H22	0.3864	0.2811	0.6151	0.049*
C23	0.44339 (5)	0.22225 (14)	0.5373 (2)	0.0504 (4)
H23	0.4639	0.2825	0.5993	0.060*
C24	0.45938 (5)	0.13514 (15)	0.4389 (2)	0.0491 (4)
H24	0.4909	0.1347	0.4339	0.059*
C25	0.42940 (5)	0.04860 (15)	0.3476 (2)	0.0480 (3)
H25	0.4404	−0.0113	0.2797	0.058*
C26	0.38362 (5)	0.04870 (13)	0.35468 (17)	0.0399 (3)
H26	0.3632	−0.0111	0.2913	0.048*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.03330 (19)	0.0913 (3)	0.0612 (3)	0.01429 (18)	0.00056 (16)	0.0042 (2)
O1	0.0324 (5)	0.0532 (6)	0.0521 (6)	−0.0033 (4)	0.0008 (4)	0.0226 (5)
N1	0.0310 (6)	0.0492 (7)	0.0523 (7)	−0.0030 (5)	0.0042 (5)	0.0185 (6)
C1	0.0321 (6)	0.0295 (5)	0.0294 (5)	0.0008 (4)	0.0095 (4)	0.0000 (4)
C2	0.0312 (6)	0.0296 (6)	0.0435 (7)	0.0008 (5)	0.0074 (5)	0.0034 (5)
C3	0.0353 (6)	0.0426 (7)	0.0338 (6)	−0.0007 (5)	0.0076 (5)	−0.0058 (5)
C11	0.0320 (5)	0.0282 (5)	0.0294 (5)	0.0029 (4)	0.0093 (4)	−0.0022 (4)
C12	0.0383 (6)	0.0325 (6)	0.0343 (6)	0.0027 (5)	0.0108 (5)	0.0022 (5)
C13	0.0434 (7)	0.0421 (7)	0.0359 (6)	0.0129 (6)	0.0088 (5)	0.0065 (5)
C14	0.0304 (6)	0.0504 (7)	0.0355 (6)	0.0099 (5)	0.0066 (5)	−0.0044 (6)
C15	0.0326 (6)	0.0397 (7)	0.0449 (7)	−0.0007 (5)	0.0106 (5)	−0.0045 (5)
C16	0.0347 (6)	0.0306 (6)	0.0413 (6)	0.0023 (5)	0.0092 (5)	0.0028 (5)
C21	0.0326 (6)	0.0332 (6)	0.0290 (5)	−0.0006 (4)	0.0036 (4)	0.0011 (5)
C22	0.0439 (7)	0.0338 (6)	0.0428 (7)	−0.0031 (5)	0.0054 (5)	−0.0050 (5)
C23	0.0421 (8)	0.0454 (8)	0.0583 (9)	−0.0138 (6)	0.0002 (6)	0.0011 (7)
C24	0.0320 (7)	0.0534 (9)	0.0615 (9)	0.0014 (6)	0.0099 (6)	0.0110 (7)
C25	0.0443 (8)	0.0490 (8)	0.0529 (8)	0.0073 (6)	0.0160 (6)	−0.0014 (7)
C26	0.0385 (7)	0.0413 (7)	0.0390 (7)	−0.0019 (5)	0.0069 (5)	−0.0068 (6)

Geometric parameters (Å, º) top

Cl1—C14	1.7372 (14)	C13—H13	0.9500
O1—N1	1.4121 (14)	C14—C15	1.385 (2)
O1—C3	1.4597 (18)	C15—C16	1.3816 (18)
N1—C1	1.2818 (17)	C15—H15	0.9500
C1—C11	1.4688 (16)	C16—H16	0.9500
C1—C2	1.4985 (17)	C21—C26	1.3853 (19)
C2—C3	1.5277 (19)	C21—C22	1.3859 (18)
C2—H2A	0.9900	C22—C23	1.393 (2)
C2—H2B	0.9900	C22—H22	0.9500
C3—C21	1.5043 (18)	C23—C24	1.380 (2)
C3—H3	1.0000	C23—H23	0.9500
C11—C12	1.3936 (17)	C24—C25	1.380 (2)
C11—C16	1.3979 (18)	C24—H24	0.9500
C12—C13	1.3893 (18)	C25—C26	1.378 (2)
C12—H12	0.9500	C25—H25	0.9500
C13—C14	1.380 (2)	C26—H26	0.9500

N1—O1—C3	108.20 (9)	C13—C14—Cl1	119.96 (11)
C1—N1—O1	109.39 (10)	C15—C14—Cl1	118.45 (11)
N1—C1—C11	120.17 (11)	C16—C15—C14	119.06 (12)
N1—C1—C2	113.33 (11)	C16—C15—H15	120.5
C11—C1—C2	126.46 (10)	C14—C15—H15	120.5
C1—C2—C3	100.08 (10)	C15—C16—C11	120.79 (12)
C1—C2—H2A	111.8	C15—C16—H16	119.6
C3—C2—H2A	111.8	C11—C16—H16	119.6
C1—C2—H2B	111.8	C26—C21—C22	119.26 (12)
C3—C2—H2B	111.8	C26—C21—C3	121.01 (11)
H2A—C2—H2B	109.5	C22—C21—C3	119.73 (12)
O1—C3—C21	108.85 (10)	C21—C22—C23	120.04 (13)
O1—C3—C2	103.42 (10)	C21—C22—H22	120.0
C21—C3—C2	117.74 (11)	C23—C22—H22	120.0
O1—C3—H3	108.8	C24—C23—C22	120.07 (13)
C21—C3—H3	108.8	C24—C23—H23	120.0
C2—C3—H3	108.8	C22—C23—H23	120.0
C12—C11—C16	118.86 (11)	C23—C24—C25	119.78 (14)
C12—C11—C1	120.90 (11)	C23—C24—H24	120.1
C16—C11—C1	120.22 (11)	C25—C24—H24	120.1
C13—C12—C11	120.73 (12)	C26—C25—C24	120.30 (14)
C13—C12—H12	119.6	C26—C25—H25	119.8
C11—C12—H12	119.6	C24—C25—H25	119.8
C14—C13—C12	118.98 (12)	C25—C26—C21	120.55 (13)
C14—C13—H13	120.5	C25—C26—H26	119.7
C12—C13—H13	120.5	C21—C26—H26	119.7
C13—C14—C15	121.58 (12)

C3—O1—N1—C1	13.27 (15)	C13—C14—C15—C16	−0.6 (2)
O1—N1—C1—C11	−179.87 (10)	Cl1—C14—C15—C16	179.98 (10)
O1—N1—C1—C2	2.47 (16)	C14—C15—C16—C11	0.26 (19)
N1—C1—C2—C3	−15.95 (14)	C12—C11—C16—C15	0.04 (18)
C11—C1—C2—C3	166.57 (11)	C1—C11—C16—C15	178.79 (11)
N1—O1—C3—C21	−148.44 (11)	O1—C3—C21—C26	44.82 (16)
N1—O1—C3—C2	−22.50 (13)	C2—C3—C21—C26	−72.34 (16)
C1—C2—C3—O1	21.97 (12)	O1—C3—C21—C22	−134.27 (12)
C1—C2—C3—C21	142.02 (11)	C2—C3—C21—C22	108.56 (14)
N1—C1—C11—C12	179.87 (12)	C26—C21—C22—C23	0.8 (2)
C2—C1—C11—C12	−2.81 (18)	C3—C21—C22—C23	179.87 (12)
N1—C1—C11—C16	1.15 (18)	C21—C22—C23—C24	−1.0 (2)
C2—C1—C11—C16	178.47 (12)	C22—C23—C24—C25	0.7 (2)
C16—C11—C12—C13	0.01 (18)	C23—C24—C25—C26	−0.1 (2)
C1—C11—C12—C13	−178.73 (11)	C24—C25—C26—C21	−0.1 (2)
C11—C12—C13—C14	−0.36 (19)	C22—C21—C26—C25	−0.2 (2)
C12—C13—C14—C15	0.7 (2)	C3—C21—C26—C25	−179.31 (13)
C12—C13—C14—Cl1	−179.94 (10)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C11–C16 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···N1ⁱ	0.95	2.74	3.657 (2)	163
C12—H12···O1ⁱ	0.95	2.65	3.390 (2)	135
C2—H2B···O1ⁱⁱ	0.99	2.67	3.466 (2)	138
C26—H26···O1ⁱⁱ	0.95	2.70	3.431 (2)	134
C22—H22···Cgⁱⁱⁱ	0.95	2.81	3.721 (3)	162

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₂ClNO
M_r	257.71
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	200
a, b, c (Å)	29.797 (5), 10.717 (5), 8.086 (5)
β (°)	103.088 (5)
V (Å³)	2515 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.29
Crystal size (mm)	0.58 × 0.42 × 0.21

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.850, 0.943
No. of measured, independent and observed [I > 2σ(I)] reflections	11843, 3132, 2637
R_int	0.014
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.103, 1.03
No. of reflections	3132
No. of parameters	163
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.23

Computer programs: APEX2 (Bruker, 2010), SAINT (Bruker, 2010), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C11–C16 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···N1ⁱ	0.95	2.74	3.657 (2)	163
C12—H12···O1ⁱ	0.95	2.65	3.390 (2)	135
C2—H2B···O1ⁱⁱ	0.99	2.67	3.466 (2)	138
C26—H26···O1ⁱⁱ	0.95	2.70	3.431 (2)	134
C22—H22···Cgⁱⁱⁱ	0.95	2.81	3.721 (3)	162

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

Acknowledgements

AMI is thankful to the Department of Atomic Energy, Board for Research in Nuclear Sciences, Government of India, for the Young Scientist award.

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