2-(1,3-Benzodioxol-5-yl)-3-phenyl­quinazolin-4(3H)-one

Chandra; Raghavendra, G.M.; Jeyaseelan, S.; Mantelingu, K.; Mahendra, M.

doi:10.1107/S1600536813016346

organic compounds

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ISSN: 2056-9890

Volume 69| Part 7| July 2013| Page o1113

https://doi.org/10.1107/S1600536813016346

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2-(1,3-Benzodioxol-5-yl)-3-phenylquinazolin-4(3H)-one

Chandra,^a G. M. Raghavendra,^b S. Jeyaseelan,^c K. Mantelingu ^b and M. Mahendra ^a ^*

^aDepartment of Studies in Physics, Manasagangotri, University of Mysore, Mysore 570 006, India, ^bDepartment of Studies in Chemistry, Manasagangotri, University of Mysore, Mysore 570 006, India, and ^cDepartment of Physics, St Philomena's College, Mysore, India
^*Correspondence e-mail: mahendra@physics.uni-mysore.ac.in

(Received 7 June 2013; accepted 12 June 2013; online 19 June 2013)

In the molecule of the title compound, C₂₁H₁₄N₂O₃, the quinazoline ring system [maximum deviation = 0.076 (1) Å] makes dihedral angles of 40.57 (9) and 42.31 (11)°, respectively, with the phenyl and 1,3-benzodioxole rings. The dihedral angle between the phenyl ring and the 1,3-benzodioxole ring is 4.34 (10)°. In the crystal, C—H⋯O hydrogen bonds link the molecules into infinite zigzag chains extending along [100].

Related literature

For the biological and pharmaceutical importance of quinazolines, see: Arfan et al. (2008 ); Bartroli et al. (1998 ); Kung et al. (1999 ); Mannschreck et al. (1984 ).

Experimental

Crystal data

C₂₁H₁₄N₂O₃
M_r = 342.34
Monoclinic, P 2₁
a = 8.984 (4) Å
b = 6.056 (3) Å
c = 15.248 (6) Å
β = 95.357 (6)°
V = 826.0 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 273 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
9157 measured reflections
3751 independent reflections
3163 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.101
S = 1.04
3751 reflections
235 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17⋯O5ⁱ	0.93	2.37	3.185 (3)	146
C25—H23A⋯O5ⁱⁱ	0.97	2.49	3.416 (3)	160
Symmetry codes: (i) x, y+1, z; (ii) x-1, y+1, z.

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536813016346/fk2072sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813016346/fk2072Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813016346/fk2072Isup3.cml

checkCIF report

Comment top

Quinazoline and their derivatives are an interesting class of heterocyclic compounds that have drawn much attention because of their biological and pharmaceutical activities; such as anti-bacterial (Kung et al., 1999), antimicrobial (Arfan et al., 2008) antifungal (Bartroli et al., 1998) and anticonvulsant activities (Mannschreck et al., 1984). In view of their importance, the crystal structure determination of the title compound was carried out and the results are presented herein.

In the molecular structure of the title compound (Fig. 1), the dihedral angles between the quinazoline moiety (N3–C4/C6–C11/N1–C2) and the phenyl ring (C12/C13/C14/C15/C16/C17) as well as the 1,3-benzodioxole ring (C18–C19/C20–C24/C25–C26) are 40.57 (9)° and 42.31 (11)°, respectively. The dihedral angle between the phenyl ring (C12/C13/C14/C15/C16/C17) and 1,3-benzodioxole ring (C18–C19/C20–C24/C25–C26) is 4.34 (10)°. The crystal packing exhibits intermolecular C—H···O interactions (Fig. 2) that link molecules into endless zig-zag chains extended along [100].

Related literature top

For the biological and pharmaceutical importance of quinazolines, see: Arfan et al. (2008); Bartroli et al. (1998); Kung et al. (1999); Mannschreck et al. (1984).

Experimental top

To a solution of 2-amino-N-phenylbenzamide (1 mmol) and benzo[d][1,3]dioxole-5-carbaldehyde (1 mmol) in ethyl acetate (2 ml) was added propyl phosphonic anhydride (1 mmol) and the reaction mixture was stirred for about 2 hrs at room temperature, then 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) (1 mmol) was added and stirred for about 30 minutes. The reaction mixture was diluted with water and extracted to ethyl acetate and it was washed with 10% NaHCO3, water, brine solution and dried over anhydrous sodium sulfate and concentrated under reduced pressure to get a crude product which was recrystalized by slow evaporation in ethyl acetate at room temperature to get the title compound.

Structure description top

For the biological and pharmaceutical importance of quinazolines, see: Arfan et al. (2008); Bartroli et al. (1998); Kung et al. (1999); Mannschreck et al. (1984).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound with anisotropic displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Packing diagram of the molecule viewed along b-axis. Intermolecular hydrogen bonding drawn as dotted lines.

2-(1,3-Benzodioxol-5-yl)-3-phenylquinazolin-4(3H)-one top

Crystal data top

C₂₁H₁₄N₂O₃	F(000) = 356
M_r = 342.34	D_x = 1.377 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 3751 reflections
a = 8.984 (4) Å	θ = 1.3–28.0°
b = 6.056 (3) Å	µ = 0.09 mm⁻¹
c = 15.248 (6) Å	T = 273 K
β = 95.357 (6)°	Block, yellow
V = 826.0 (6) Å³	0.30 × 0.25 × 0.20 mm
Z = 2

Data collection top

Bruker APEXII CCD area-detector diffractometer	R_int = 0.023
ω and φ scans	θ_max = 28.0°, θ_min = 1.3°
9157 measured reflections	h = −11→11
3751 independent reflections	k = −8→7
3163 reflections with I > 2σ(I)	l = −19→19

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.101	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0558P)² + 0.0215P] where P = (F_o² + 2F_c²)/3
3751 reflections	(Δ/σ)_max < 0.001
235 parameters	Δρ_max = 0.16 e Å⁻³
1 restraint	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₂₁H₁₄N₂O₃	V = 826.0 (6) Å³
M_r = 342.34	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 8.984 (4) Å	µ = 0.09 mm⁻¹
b = 6.056 (3) Å	T = 273 K
c = 15.248 (6) Å	0.30 × 0.25 × 0.20 mm
β = 95.357 (6)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3163 reflections with I > 2σ(I)
9157 measured reflections	R_int = 0.023
3751 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	1 restraint
wR(F²) = 0.101	H-atom parameters constrained
S = 1.04	Δρ_max = 0.16 e Å⁻³
3751 reflections	Δρ_min = −0.20 e Å⁻³
235 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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
O5	1.05179 (14)	0.2056 (2)	0.70071 (8)	0.0591 (4)
O24	0.44816 (14)	1.2103 (3)	0.88187 (8)	0.0637 (4)
O26	0.47712 (16)	1.2832 (2)	0.73629 (9)	0.0690 (5)
N1	0.69195 (15)	0.5808 (3)	0.61645 (9)	0.0552 (5)
N3	0.88645 (14)	0.4809 (2)	0.72424 (8)	0.0416 (4)
C2	0.76074 (16)	0.6048 (3)	0.69362 (10)	0.0435 (5)
C4	0.93930 (17)	0.3085 (3)	0.67377 (10)	0.0443 (5)
C6	0.85398 (17)	0.2701 (3)	0.58978 (11)	0.0490 (5)
C7	0.8883 (2)	0.0937 (4)	0.53638 (13)	0.0621 (7)
C8	0.8062 (2)	0.0598 (5)	0.45769 (15)	0.0835 (9)
C9	0.6918 (3)	0.2064 (6)	0.42996 (16)	0.1048 (12)
C10	0.6579 (3)	0.3796 (6)	0.48092 (14)	0.0923 (9)
C11	0.73748 (19)	0.4136 (4)	0.56322 (11)	0.0569 (6)
C12	0.98242 (16)	0.5453 (3)	0.80117 (9)	0.0413 (5)
C13	1.00197 (18)	0.4050 (3)	0.87253 (10)	0.0487 (5)
C14	1.09842 (19)	0.4651 (4)	0.94460 (12)	0.0591 (6)
C15	1.1735 (2)	0.6638 (4)	0.94456 (12)	0.0608 (7)
C16	1.15312 (19)	0.8023 (3)	0.87348 (13)	0.0588 (6)
C17	1.05718 (18)	0.7432 (3)	0.80046 (11)	0.0490 (5)
C18	0.69538 (15)	0.7673 (3)	0.75203 (10)	0.0423 (5)
C19	0.67842 (17)	0.7258 (3)	0.84001 (10)	0.0484 (5)
C20	0.59554 (18)	0.8651 (3)	0.88969 (11)	0.0526 (6)
C21	0.53344 (17)	1.0466 (3)	0.84817 (11)	0.0476 (5)
C22	0.55001 (18)	1.0905 (3)	0.76149 (11)	0.0490 (5)
C23	0.62930 (17)	0.9549 (3)	0.71145 (10)	0.0471 (5)
C25	0.3916 (2)	1.3373 (4)	0.80727 (13)	0.0644 (7)
H7	0.96700	−0.00050	0.55440	0.0750*
H8	0.82650	−0.06040	0.42280	0.1000*
H9	0.63780	0.18510	0.37560	0.1260*
H10	0.58160	0.47610	0.46110	0.1110*
H13	0.95090	0.27130	0.87220	0.0580*
H14	1.11260	0.37170	0.99310	0.0710*
H15	1.23820	0.70390	0.99310	0.0730*
H16	1.20370	0.93640	0.87410	0.0710*
H17	1.04380	0.83620	0.75180	0.0590*
H19	0.72360	0.60150	0.86660	0.0580*
H20	0.58330	0.83540	0.94840	0.0630*
H23A	0.28690	1.30300	0.79170	0.0770*
H23B	0.40020	1.49370	0.82050	0.0770*
H26	0.63900	0.98610	0.65250	0.0570*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O5	0.0584 (7)	0.0551 (7)	0.0635 (7)	0.0186 (6)	0.0045 (6)	0.0065 (6)
O24	0.0545 (7)	0.0728 (9)	0.0645 (7)	0.0097 (7)	0.0101 (6)	−0.0164 (7)
O26	0.0705 (9)	0.0601 (8)	0.0795 (8)	0.0209 (7)	0.0228 (7)	0.0092 (7)
N1	0.0408 (7)	0.0766 (11)	0.0470 (7)	0.0126 (8)	−0.0016 (6)	−0.0096 (8)
N3	0.0370 (6)	0.0445 (7)	0.0430 (6)	0.0033 (6)	0.0025 (5)	0.0029 (6)
C2	0.0338 (7)	0.0526 (10)	0.0441 (8)	0.0033 (7)	0.0035 (6)	0.0023 (7)
C4	0.0430 (8)	0.0414 (9)	0.0497 (9)	0.0006 (7)	0.0105 (7)	0.0053 (7)
C6	0.0392 (8)	0.0560 (11)	0.0533 (9)	−0.0022 (8)	0.0125 (7)	−0.0040 (8)
C7	0.0522 (10)	0.0674 (13)	0.0688 (11)	−0.0017 (9)	0.0163 (9)	−0.0163 (10)
C8	0.0590 (12)	0.108 (2)	0.0847 (14)	0.0021 (14)	0.0134 (11)	−0.0491 (15)
C9	0.0626 (13)	0.169 (3)	0.0792 (14)	0.0229 (17)	−0.0125 (11)	−0.0633 (17)
C10	0.0616 (12)	0.142 (2)	0.0694 (13)	0.0328 (15)	−0.0145 (10)	−0.0415 (15)
C11	0.0403 (8)	0.0769 (13)	0.0534 (9)	0.0035 (9)	0.0033 (7)	−0.0150 (9)
C12	0.0325 (7)	0.0455 (9)	0.0458 (8)	0.0052 (7)	0.0040 (6)	0.0019 (7)
C13	0.0408 (8)	0.0539 (10)	0.0514 (9)	0.0014 (8)	0.0039 (6)	0.0096 (8)
C14	0.0481 (9)	0.0804 (14)	0.0480 (9)	0.0125 (10)	0.0005 (7)	0.0101 (9)
C15	0.0433 (9)	0.0767 (15)	0.0607 (11)	0.0098 (9)	−0.0041 (8)	−0.0119 (10)
C16	0.0437 (9)	0.0525 (10)	0.0799 (12)	−0.0023 (9)	0.0036 (8)	−0.0120 (10)
C17	0.0425 (8)	0.0440 (9)	0.0601 (10)	0.0036 (7)	0.0026 (7)	0.0071 (8)
C18	0.0303 (7)	0.0518 (9)	0.0444 (8)	0.0002 (7)	0.0013 (6)	−0.0016 (7)
C19	0.0390 (8)	0.0597 (10)	0.0458 (8)	0.0077 (8)	0.0001 (6)	0.0028 (8)
C20	0.0425 (8)	0.0740 (13)	0.0413 (8)	0.0036 (9)	0.0035 (6)	−0.0016 (8)
C21	0.0345 (7)	0.0593 (11)	0.0487 (8)	−0.0016 (7)	0.0031 (6)	−0.0131 (8)
C22	0.0395 (8)	0.0478 (9)	0.0599 (10)	0.0020 (8)	0.0064 (7)	−0.0001 (8)
C23	0.0395 (8)	0.0580 (10)	0.0443 (8)	0.0009 (8)	0.0063 (6)	0.0022 (8)
C25	0.0517 (10)	0.0643 (12)	0.0785 (12)	0.0096 (9)	0.0130 (9)	−0.0074 (10)

Geometric parameters (Å, º) top

O5—C4	1.225 (2)	C15—C16	1.369 (3)
O24—C21	1.381 (2)	C16—C17	1.390 (3)
O24—C25	1.427 (3)	C18—C19	1.387 (2)
O26—C22	1.375 (2)	C18—C23	1.399 (3)
O26—C25	1.423 (2)	C19—C20	1.395 (2)
N1—C2	1.285 (2)	C20—C21	1.362 (3)
N1—C11	1.383 (3)	C21—C22	1.370 (2)
N3—C2	1.399 (2)	C22—C23	1.366 (2)
N3—C4	1.406 (2)	C7—H7	0.9300
N3—C12	1.443 (2)	C8—H8	0.9300
C2—C18	1.485 (2)	C9—H9	0.9300
C4—C6	1.449 (2)	C10—H10	0.9300
C6—C7	1.395 (3)	C13—H13	0.9300
C6—C11	1.391 (3)	C14—H14	0.9300
C7—C8	1.364 (3)	C15—H15	0.9300
C8—C9	1.394 (4)	C16—H16	0.9300
C9—C10	1.357 (5)	C17—H17	0.9300
C10—C11	1.400 (3)	C19—H19	0.9300
C12—C13	1.379 (2)	C20—H20	0.9300
C12—C17	1.374 (3)	C23—H26	0.9300
C13—C14	1.383 (3)	C25—H23A	0.9700
C14—C15	1.380 (3)	C25—H23B	0.9700

C21—O24—C25	105.01 (14)	O24—C21—C22	109.49 (15)
C22—O26—C25	105.05 (14)	C20—C21—C22	121.91 (16)
C2—N1—C11	118.47 (15)	O26—C22—C21	110.03 (15)
C2—N3—C4	121.26 (13)	O26—C22—C23	127.86 (15)
C2—N3—C12	121.91 (13)	C21—C22—C23	122.12 (16)
C4—N3—C12	116.04 (12)	C18—C23—C22	117.59 (14)
N1—C2—N3	123.30 (15)	O24—C25—O26	107.75 (16)
N1—C2—C18	116.16 (14)	C6—C7—H7	120.00
N3—C2—C18	120.49 (13)	C8—C7—H7	120.00
O5—C4—N3	120.30 (14)	C7—C8—H8	120.00
O5—C4—C6	124.52 (16)	C9—C8—H8	120.00
N3—C4—C6	115.17 (14)	C8—C9—H9	119.00
C4—C6—C7	120.76 (16)	C10—C9—H9	119.00
C4—C6—C11	118.60 (16)	C9—C10—H10	120.00
C7—C6—C11	120.64 (16)	C11—C10—H10	120.00
C6—C7—C8	119.9 (2)	C12—C13—H13	120.00
C7—C8—C9	119.6 (2)	C14—C13—H13	120.00
C8—C9—C10	121.2 (2)	C13—C14—H14	120.00
C9—C10—C11	120.3 (3)	C15—C14—H14	120.00
N1—C11—C6	122.83 (15)	C14—C15—H15	120.00
N1—C11—C10	118.6 (2)	C16—C15—H15	120.00
C6—C11—C10	118.4 (2)	C15—C16—H16	120.00
N3—C12—C13	119.83 (15)	C17—C16—H16	120.00
N3—C12—C17	118.99 (14)	C12—C17—H17	120.00
C13—C12—C17	121.15 (14)	C16—C17—H17	120.00
C12—C13—C14	119.28 (17)	C18—C19—H19	119.00
C13—C14—C15	119.95 (18)	C20—C19—H19	119.00
C14—C15—C16	120.36 (17)	C19—C20—H20	122.00
C15—C16—C17	120.23 (17)	C21—C20—H20	122.00
C12—C17—C16	119.03 (16)	C18—C23—H26	121.00
C2—C18—C19	123.05 (16)	C22—C23—H26	121.00
C2—C18—C23	116.63 (14)	O24—C25—H23A	110.00
C19—C18—C23	119.63 (15)	O24—C25—H23B	110.00
C18—C19—C20	121.88 (16)	O26—C25—H23A	110.00
C19—C20—C21	116.88 (15)	O26—C25—H23B	110.00
O24—C21—C20	128.60 (15)	H23A—C25—H23B	108.00

C25—O24—C21—C20	−170.35 (18)	C11—C6—C7—C8	−0.6 (3)
C25—O24—C21—C22	9.67 (19)	C4—C6—C11—N1	−5.3 (3)
C21—O24—C25—O26	−15.83 (19)	C4—C6—C11—C10	178.3 (2)
C25—O26—C22—C21	−10.09 (19)	C7—C6—C11—N1	175.08 (18)
C25—O26—C22—C23	170.00 (18)	C7—C6—C11—C10	−1.4 (3)
C22—O26—C25—O24	15.97 (19)	C6—C7—C8—C9	2.2 (3)
C11—N1—C2—N3	4.8 (3)	C7—C8—C9—C10	−1.7 (4)
C11—N1—C2—C18	−172.49 (16)	C8—C9—C10—C11	−0.4 (4)
C2—N1—C11—C6	0.3 (3)	C9—C10—C11—N1	−174.8 (2)
C2—N1—C11—C10	176.7 (2)	C9—C10—C11—C6	1.9 (4)
C4—N3—C2—N1	−4.8 (2)	N3—C12—C13—C14	177.68 (15)
C4—N3—C2—C18	172.43 (14)	C17—C12—C13—C14	0.1 (3)
C12—N3—C2—N1	164.67 (16)	N3—C12—C17—C16	−178.07 (15)
C12—N3—C2—C18	−18.1 (2)	C13—C12—C17—C16	−0.5 (2)
C2—N3—C4—O5	178.13 (15)	C12—C13—C14—C15	0.1 (3)
C2—N3—C4—C6	−0.4 (2)	C13—C14—C15—C16	0.0 (3)
C12—N3—C4—O5	8.1 (2)	C14—C15—C16—C17	−0.4 (3)
C12—N3—C4—C6	−170.47 (14)	C15—C16—C17—C12	0.6 (3)
C2—N3—C12—C13	120.18 (17)	C2—C18—C19—C20	−169.50 (15)
C2—N3—C12—C17	−62.2 (2)	C23—C18—C19—C20	0.7 (2)
C4—N3—C12—C13	−69.84 (18)	C2—C18—C23—C22	170.86 (14)
C4—N3—C12—C17	107.81 (17)	C19—C18—C23—C22	0.1 (2)
N1—C2—C18—C19	135.61 (17)	C18—C19—C20—C21	−1.0 (2)
N1—C2—C18—C23	−34.8 (2)	C19—C20—C21—O24	−179.44 (16)
N3—C2—C18—C19	−41.8 (2)	C19—C20—C21—C22	0.5 (2)
N3—C2—C18—C23	147.76 (15)	O24—C21—C22—O26	0.25 (19)
O5—C4—C6—C7	6.2 (3)	O24—C21—C22—C23	−179.83 (16)
O5—C4—C6—C11	−173.46 (17)	C20—C21—C22—O26	−179.74 (15)
N3—C4—C6—C7	−175.32 (16)	C20—C21—C22—C23	0.2 (3)
N3—C4—C6—C11	5.0 (2)	O26—C22—C23—C18	179.41 (16)
C4—C6—C7—C8	179.72 (19)	C21—C22—C23—C18	−0.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···O5ⁱ	0.93	2.37	3.185 (3)	146
C25—H23A···O5ⁱⁱ	0.97	2.49	3.416 (3)	160

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

Experimental details

Crystal data
Chemical formula	C₂₁H₁₄N₂O₃
M_r	342.34
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	273
a, b, c (Å)	8.984 (4), 6.056 (3), 15.248 (6)
β (°)	95.357 (6)
V (Å³)	826.0 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	9157, 3751, 3163
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.101, 1.04
No. of reflections	3751
No. of parameters	235
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.20

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···O5ⁱ	0.93	2.37	3.185 (3)	145.8
C25—H23A···O5ⁱⁱ	0.97	2.49	3.416 (3)	160.0

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

Acknowledgements

Chandra would like to thank the University of Mysore for the award of an RFSMS fellowship under the head DV5/Physics/389/RFSMS/2009–2010/10.07.2012.

References

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