8-Bromo-3-phenyl-3a,4-dihydro-3H-chromeno[4,3-c]isoxazole-3a-carbo­nitrile

Suresh, G.; Srinivasan, J.; Bakthadoss, M.; Aravindhan, S.

doi:10.1107/S1600536813002511

organic compounds

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ISSN: 2056-9890

Volume 69| Part 2| February 2013| Page o312

doi:10.1107/S1600536813002511

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8-Bromo-3-phenyl-3a,4-dihydro-3H-chromeno[4,3-c]isoxazole-3a-carbonitrile

G. Suresh,^a J. Srinivasan,^b M. Bakthadoss ^b and S. Aravindhan ^a ^*

^aDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, and ^bDepartment of Organic Chemistry, University of Madras, Chennai 600 025, India
^*Correspondence e-mail: aravindhanpresidency@gmail.com

(Received 28 December 2012; accepted 24 January 2013; online 31 January 2013)

In the title compound, C₁₇H₁₁BrN₂O₂, the five-membered isoxazole ring has an envelope conformation with the C atom bearing the phenyl ring as the flap. The pyran ring has a half-chair conformation. In the chromeno ring system, the dihedral angle between the mean plane of the pyran ring and the benzene ring is 4.68 (2)°. The dihedral angle between the mean planes of the chromeno ring system and the isoxazole ring is 13.79 (15)°. The latter forms a dihedral angle of 34.10 (17)° with the phenyl ring. In the crystal, molecules are linked by C—H⋯N hydrogen bonds, forming an undulating two-dimensional network parallel to the ab plane.

Related literature

For the biological importance of 4H-chromene derivatives, see: Cai (2007 , 2008 ); Cai et al. (2006 ); Caine (1993 ); Gabor (1988 ); Brooks (1998 ); Valenti et al. (1993 ); Hyana & Saimoto (1987 ); Tang et al. (2007 ). For related structures, see: Gangadharan et al. (2011 ); Swaminathan et al. (2011 ). For puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₇H₁₁BrN₂O₂
M_r = 355.19
Monoclinic, P 2₁ /c
a = 15.1034 (8) Å
b = 6.0676 (3) Å
c = 16.0865 (10) Å
β = 99.953 (2)°
V = 1452.00 (14) Å³
Z = 4
Mo Kα radiation
μ = 2.84 mm⁻¹
T = 298 K
0.35 × 0.28 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.437, T_max = 0.601
9947 measured reflections
3175 independent reflections
2214 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.102
S = 1.09
3175 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.68 e Å⁻³
Δρ_min = −0.96 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯N2ⁱ	0.93	2.62	3.519 (5)	164
C15—H15⋯N2ⁱⁱ	0.93	2.61	3.334 (5)	135
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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: ORTEP-3 for Windows (Farrugia, 2012 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97 and PLATON.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813002511/su2547sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813002511/su2547Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813002511/su2547Isup3.cml

checkCIF report

Comment top

4H-Chromenes are biologically important compounds used as synthetic ligands in the design of drugs and discovery processes. They exhibit numerous biological and pharmacological properties, such as anti-viral, anti-fungal, anti-inflammatory, anti- diabetic, cardionthonic, anti anaphylactic and anti-cancer activity (Cai, 2008, 2007; Cai et al., 2006; Gabor, 1988; Brooks, 1998; Valenti et al., 1993; Hyana & Saimoto, 1987; Tang et al., 2007). Chromenopyrrole compounds are used in the treatment of impulsive disorders (Caine, 1993). Continuing our interest in such compounds we have synthesized the title compound and report herein on its crystal structure.

The molecular structure of the title molecule is illustrated in Fig. 1. The five-membered isoxazole ring (N1/O2/C7/C8/C6) adopts an envelope conformation with atom C7 as the flap: puckering parameters (Cremer & Pople, 1975) being q2 = 0.28795 (2) Å and Φ = 143.4 (2)°. In the chromeno ring system, the dihedral angle between the mean plane of the pyran ring and the benzene ring is 4.68 (2)°. The dihedral angle between the mean planes of the chromeno ring system (fusion of benzene and pyran rings) and the isoxazole ring is 13.79 (15)°. The isoxazole ring mean planes forms a dihedral angle of 34.10 (17)° with phenyl ring (C11—C16). The dihedral angle between the chromeno ring system mean plane and this phenyl ring is 25.42 (13)°. The atom Br1 deviates by 0.0379 (5) Å from the chromeno ring mean plane (O1,C1—C6/C8—C10). The geometric parameters of the title molecule agree well with those reported for closely related structures (Gangadharan et al., 2011; Swaminathan et al., 2011).

In the crystal, molecules are linked by intermolecular C—H···N hydrogen bonds forming an undulating two-dimensional network parallel to the ab plane (Fig. 2 and Table 1).

Related literature top

For the biological importance of 4H-chromene derivatives, see: Cai (2007, 2008); Cai et al. (2006); Caine (1993); Gabor (1988); Brooks (1998); Valenti et al. (1993); Hyana & Saimoto (1987); Tang et al. (2007). For related structures, see: Gangadharan et al. (2011); Swaminathan et al. (2011). For puckering parameters, see: Cremer & Pople (1975).

Experimental top

To a solution of (E)-2-((4-bromo-2-((E)-(hydroxyimino)methyl)phenoxy)methyl) -3-phenylacrylonitrile (2 mmol) in CCl₄ at 273 - 283 K was added pinch wise NCS (4 mmol) over 3 h. After Et₃N (4 mmol) was added to the reaction mixture which was stirred at room temperature for 2 h. After completion of the reaction, the mixture was evaporated under reduced pressure and the resulting crude mass was diluted with water (15 ml) and extracted with ethyl acetate (3 × 15 ml). The combining organic layer was washed with brine (2 × 10 ml) and dried over anhydrous Na₂SO₄. The organic layer was evaporated and purified by column chromatography (silica gel 60–120 mesh; 7% EtOAc in hexanes) to provide the desired pure title product as a colourless solid. Single crystals suitable for X-ray diffraction were obtained by slow evaporation of a solution of the title compound in ethyl acetate at room temperature.

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: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title molecule, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A view along the b axis of the crystal packing of the title compound. The molecules are linked by C—H···N hydrogen bonds (dashed lines; see Table 1 for details).

8-Bromo-3-phenyl-3a,4-dihydro-3H-chromeno[4,3-c]isoxazole-3a-carbonitrile top

Crystal data top

C₁₇H₁₁BrN₂O₂	F(000) = 712
M_r = 355.19	D_x = 1.625 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3175 reflections
a = 15.1034 (8) Å	θ = 2.6–28.6°
b = 6.0676 (3) Å	µ = 2.84 mm⁻¹
c = 16.0865 (10) Å	T = 298 K
β = 99.953 (2)°	Block, colourless
V = 1452.00 (14) Å³	0.35 × 0.28 × 0.20 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	3175 independent reflections
Radiation source: fine-focus sealed tube	2214 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ω and ϕ scans	θ_max = 28.6°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −20→17
T_min = 0.437, T_max = 0.601	k = −7→6
9947 measured reflections	l = −21→20

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.102	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0261P)² + 2.1957P] where P = (F_o² + 2F_c²)/3
3175 reflections	(Δ/σ)_max = 0.001
199 parameters	Δρ_max = 0.68 e Å⁻³
0 restraints	Δρ_min = −0.96 e Å⁻³

Crystal data top

C₁₇H₁₁BrN₂O₂	V = 1452.00 (14) Å³
M_r = 355.19	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.1034 (8) Å	µ = 2.84 mm⁻¹
b = 6.0676 (3) Å	T = 298 K
c = 16.0865 (10) Å	0.35 × 0.28 × 0.20 mm
β = 99.953 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3175 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	2214 reflections with I > 2σ(I)
T_min = 0.437, T_max = 0.601	R_int = 0.031
9947 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.102	H-atom parameters constrained
S = 1.09	Δρ_max = 0.68 e Å⁻³
3175 reflections	Δρ_min = −0.96 e Å⁻³
199 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
Br1	0.36162 (2)	0.32449 (7)	0.91825 (3)	0.05691 (17)
C1	0.5050 (3)	−0.1845 (7)	0.8336 (2)	0.0511 (10)
H1	0.4920	−0.3179	0.8057	0.061*
C2	0.4363 (2)	−0.0557 (7)	0.8528 (2)	0.0497 (10)
H2	0.3770	−0.1023	0.8383	0.060*
C3	0.4558 (2)	0.1418 (6)	0.8935 (2)	0.0409 (8)
C4	0.5432 (2)	0.2124 (6)	0.9171 (2)	0.0388 (8)
H4	0.5555	0.3452	0.9457	0.047*
C5	0.6132 (2)	0.0817 (6)	0.8976 (2)	0.0347 (7)
C6	0.7069 (2)	0.1465 (5)	0.9180 (2)	0.0327 (7)
C7	0.8603 (2)	0.0893 (6)	0.9367 (2)	0.0350 (8)
H7	0.8709	−0.0167	0.9834	0.042*
C8	0.7744 (2)	0.0220 (5)	0.87679 (19)	0.0328 (7)
C9	0.7483 (2)	−0.2215 (6)	0.8748 (2)	0.0442 (9)
H9A	0.7887	−0.3049	0.8460	0.053*
H9B	0.7545	−0.2768	0.9321	0.053*
C10	0.5935 (2)	−0.1162 (6)	0.8556 (2)	0.0397 (8)
C11	0.9454 (2)	0.1107 (6)	0.90087 (19)	0.0335 (8)
C12	0.9955 (2)	0.3024 (6)	0.9084 (2)	0.0463 (9)
H12	0.9750	0.4258	0.9336	0.056*
C13	1.0765 (3)	0.3117 (7)	0.8784 (2)	0.0540 (10)
H13	1.1104	0.4404	0.8846	0.065*
C14	1.1064 (2)	0.1313 (7)	0.8398 (2)	0.0527 (10)
H14	1.1606	0.1374	0.8199	0.063*
C15	1.0561 (2)	−0.0576 (7)	0.8308 (2)	0.0522 (10)
H15	1.0756	−0.1793	0.8038	0.063*
C16	0.9764 (2)	−0.0679 (6)	0.8617 (2)	0.0456 (9)
H16	0.9431	−0.1976	0.8560	0.055*
C17	0.7720 (2)	0.1102 (6)	0.7912 (2)	0.0380 (8)
N1	0.74127 (18)	0.2977 (5)	0.96850 (19)	0.0449 (7)
N2	0.7691 (2)	0.1831 (7)	0.7260 (2)	0.0633 (10)
O1	0.65812 (17)	−0.2523 (4)	0.83272 (17)	0.0518 (7)
O2	0.83596 (15)	0.2996 (4)	0.96973 (16)	0.0481 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0352 (2)	0.0664 (3)	0.0693 (3)	0.00649 (18)	0.00961 (17)	0.0061 (2)
C1	0.052 (2)	0.045 (2)	0.056 (2)	−0.0149 (19)	0.0085 (18)	−0.008 (2)
C2	0.0376 (19)	0.057 (3)	0.053 (2)	−0.0119 (18)	0.0041 (17)	0.001 (2)
C3	0.0349 (17)	0.047 (2)	0.0410 (18)	0.0027 (16)	0.0061 (14)	0.0104 (17)
C4	0.0389 (17)	0.038 (2)	0.0381 (17)	0.0003 (15)	0.0040 (14)	0.0013 (16)
C5	0.0369 (17)	0.032 (2)	0.0340 (17)	−0.0008 (14)	0.0043 (14)	0.0040 (15)
C6	0.0357 (16)	0.027 (2)	0.0335 (16)	0.0036 (14)	0.0016 (13)	0.0014 (15)
C7	0.0383 (17)	0.032 (2)	0.0326 (17)	0.0088 (14)	0.0006 (14)	−0.0005 (15)
C8	0.0345 (16)	0.030 (2)	0.0336 (16)	0.0013 (14)	0.0045 (13)	−0.0002 (14)
C9	0.0441 (19)	0.030 (2)	0.060 (2)	0.0007 (16)	0.0144 (17)	−0.0027 (18)
C10	0.0440 (19)	0.035 (2)	0.0419 (19)	−0.0032 (16)	0.0114 (15)	−0.0004 (16)
C11	0.0320 (16)	0.036 (2)	0.0285 (15)	0.0068 (14)	−0.0057 (13)	0.0014 (14)
C12	0.053 (2)	0.039 (2)	0.046 (2)	0.0008 (18)	0.0048 (17)	−0.0044 (18)
C13	0.052 (2)	0.055 (3)	0.053 (2)	−0.012 (2)	0.0028 (18)	0.006 (2)
C14	0.0397 (19)	0.075 (3)	0.044 (2)	0.000 (2)	0.0071 (16)	0.008 (2)
C15	0.046 (2)	0.058 (3)	0.054 (2)	0.010 (2)	0.0119 (18)	−0.010 (2)
C16	0.0390 (18)	0.041 (2)	0.055 (2)	0.0029 (16)	0.0043 (16)	−0.0070 (19)
C17	0.0292 (16)	0.046 (2)	0.0365 (19)	−0.0046 (15)	−0.0017 (14)	0.0008 (17)
N1	0.0341 (15)	0.045 (2)	0.0549 (18)	0.0062 (14)	0.0051 (13)	−0.0105 (16)
N2	0.0420 (17)	0.095 (3)	0.049 (2)	−0.0085 (18)	−0.0012 (15)	0.022 (2)
O1	0.0490 (15)	0.0387 (15)	0.0700 (18)	−0.0083 (12)	0.0170 (13)	−0.0172 (14)
O2	0.0321 (12)	0.0495 (16)	0.0604 (16)	0.0037 (11)	0.0012 (11)	−0.0236 (13)

Geometric parameters (Å, º) top

Br1—C3	1.899 (3)	C8—C9	1.528 (5)
C1—C2	1.376 (5)	C9—O1	1.425 (4)
C1—C10	1.385 (5)	C9—H9A	0.9700
C1—H1	0.9300	C9—H9B	0.9700
C2—C3	1.373 (5)	C10—O1	1.377 (4)
C2—H2	0.9300	C11—C16	1.375 (5)
C3—C4	1.377 (5)	C11—C12	1.382 (5)
C4—C5	1.400 (5)	C12—C13	1.390 (5)
C4—H4	0.9300	C12—H12	0.9300
C5—C10	1.384 (5)	C13—C14	1.373 (6)
C5—C6	1.451 (4)	C13—H13	0.9300
C6—N1	1.275 (4)	C14—C15	1.369 (6)
C6—C8	1.512 (4)	C14—H14	0.9300
C7—O2	1.454 (4)	C15—C16	1.381 (5)
C7—C11	1.502 (4)	C15—H15	0.9300
C7—C8	1.532 (4)	C16—H16	0.9300
C7—H7	0.9800	C17—N2	1.132 (4)
C8—C17	1.472 (5)	N1—O2	1.427 (3)

C2—C1—C10	120.3 (4)	O1—C9—H9A	109.4
C2—C1—H1	119.9	C8—C9—H9A	109.4
C10—C1—H1	119.9	O1—C9—H9B	109.4
C3—C2—C1	119.6 (3)	C8—C9—H9B	109.4
C3—C2—H2	120.2	H9A—C9—H9B	108.0
C1—C2—H2	120.2	O1—C10—C5	123.2 (3)
C2—C3—C4	121.3 (3)	O1—C10—C1	116.7 (3)
C2—C3—Br1	120.2 (3)	C5—C10—C1	120.0 (3)
C4—C3—Br1	118.5 (3)	C16—C11—C12	118.6 (3)
C3—C4—C5	119.1 (3)	C16—C11—C7	119.3 (3)
C3—C4—H4	120.4	C12—C11—C7	122.1 (3)
C5—C4—H4	120.4	C11—C12—C13	120.4 (4)
C10—C5—C4	119.6 (3)	C11—C12—H12	119.8
C10—C5—C6	117.7 (3)	C13—C12—H12	119.8
C4—C5—C6	122.7 (3)	C14—C13—C12	120.1 (4)
N1—C6—C5	127.9 (3)	C14—C13—H13	119.9
N1—C6—C8	114.0 (3)	C12—C13—H13	119.9
C5—C6—C8	118.1 (3)	C15—C14—C13	119.7 (3)
O2—C7—C11	110.6 (3)	C15—C14—H14	120.2
O2—C7—C8	102.9 (2)	C13—C14—H14	120.2
C11—C7—C8	118.0 (3)	C14—C15—C16	120.1 (4)
O2—C7—H7	108.3	C14—C15—H15	119.9
C11—C7—H7	108.3	C16—C15—H15	119.9
C8—C7—H7	108.3	C11—C16—C15	121.1 (4)
C17—C8—C6	108.6 (3)	C11—C16—H16	119.5
C17—C8—C9	111.6 (3)	C15—C16—H16	119.5
C6—C8—C9	107.5 (3)	N2—C17—C8	178.2 (4)
C17—C8—C7	111.9 (3)	C6—N1—O2	108.2 (3)
C6—C8—C7	98.8 (2)	C10—O1—C9	117.3 (3)
C9—C8—C7	117.3 (3)	N1—O2—C7	107.7 (2)
O1—C9—C8	111.0 (3)

C10—C1—C2—C3	0.4 (6)	C4—C5—C10—O1	178.8 (3)
C1—C2—C3—C4	−1.3 (5)	C6—C5—C10—O1	−0.1 (5)
C1—C2—C3—Br1	178.6 (3)	C4—C5—C10—C1	−0.3 (5)
C2—C3—C4—C5	1.3 (5)	C6—C5—C10—C1	−179.2 (3)
Br1—C3—C4—C5	−178.6 (2)	C2—C1—C10—O1	−178.8 (3)
C3—C4—C5—C10	−0.5 (5)	C2—C1—C10—C5	0.4 (6)
C3—C4—C5—C6	178.3 (3)	O2—C7—C11—C16	−175.9 (3)
C10—C5—C6—N1	−166.3 (3)	C8—C7—C11—C16	−58.0 (4)
C4—C5—C6—N1	14.9 (5)	O2—C7—C11—C12	6.3 (4)
C10—C5—C6—C8	12.9 (4)	C8—C7—C11—C12	124.3 (3)
C4—C5—C6—C8	−166.0 (3)	C16—C11—C12—C13	−1.3 (5)
N1—C6—C8—C17	−99.7 (3)	C7—C11—C12—C13	176.4 (3)
C5—C6—C8—C17	81.0 (4)	C11—C12—C13—C14	1.1 (6)
N1—C6—C8—C9	139.5 (3)	C12—C13—C14—C15	0.1 (6)
C5—C6—C8—C9	−39.8 (4)	C13—C14—C15—C16	−1.1 (6)
N1—C6—C8—C7	17.1 (4)	C12—C11—C16—C15	0.3 (5)
C5—C6—C8—C7	−162.1 (3)	C7—C11—C16—C15	−177.5 (3)
O2—C7—C8—C17	88.2 (3)	C14—C15—C16—C11	0.9 (6)
C11—C7—C8—C17	−33.8 (4)	C5—C6—N1—O2	179.0 (3)
O2—C7—C8—C6	−26.0 (3)	C8—C6—N1—O2	−0.2 (4)
C11—C7—C8—C6	−148.0 (3)	C5—C10—O1—C9	18.8 (5)
O2—C7—C8—C9	−141.0 (3)	C1—C10—O1—C9	−162.1 (3)
C11—C7—C8—C9	97.0 (4)	C8—C9—O1—C10	−47.8 (4)
C17—C8—C9—O1	−62.8 (4)	C6—N1—O2—C7	−18.5 (4)
C6—C8—C9—O1	56.1 (4)	C11—C7—O2—N1	155.3 (3)
C7—C8—C9—O1	166.2 (3)	C8—C7—O2—N1	28.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···N2ⁱ	0.93	2.62	3.519 (5)	164
C15—H15···N2ⁱⁱ	0.93	2.61	3.334 (5)	135

Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x+2, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₁BrN₂O₂
M_r	355.19
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	15.1034 (8), 6.0676 (3), 16.0865 (10)
β (°)	99.953 (2)
V (Å³)	1452.00 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.84
Crystal size (mm)	0.35 × 0.28 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.437, 0.601
No. of measured, independent and observed [I > 2σ(I)] reflections	9947, 3175, 2214
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.673

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.102, 1.09
No. of reflections	3175
No. of parameters	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.68, −0.96

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···N2ⁱ	0.93	2.62	3.519 (5)	164
C15—H15···N2ⁱⁱ	0.93	2.61	3.334 (5)	135

Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x+2, y−1/2, −z+3/2.

Acknowledgements

GS and SA thank UGC, India, for financial support. GS also thanks the SAIF, IIT-Madras, for for the instrumentation facility.

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