1,3-Bis(hydroxy­meth­yl)benzimidazolin-2-one

Devarajegowda, H.C.; Madhura, V.; Palakshamurthy, B.S.; Jeyaseelan, S.; Kulkarni, M.V.

doi:10.1107/S1600536809040963

organic compounds

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Volume 65| Part 11| November 2009| Page o2735

https://doi.org/10.1107/S1600536809040963

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1,3-Bis(hydroxymethyl)benzimidazolin-2-one

H. C. Devarajegowda,^a ^* V. Madhura,^b B. S. Palakshamurthy,^a S. Jeyaseelan ^a and Manohar V. Kulkarni ^b

^aDepartment of Physics, Yuvaraja's College (Constituent College), University of Mysore, Mysore 570 005, Karnataka, India, and ^bDepartment of Chemistry, Karnatak University, Dharwad 580 003, Karnataka, India
^*Correspondence e-mail: devarajegowda@yahoo.com

(Received 24 September 2009; accepted 7 October 2009; online 17 October 2009)

The title compound, C₉H₁₀N₂O₃, crystallizes with one and a half molecules in the asymmetric unit, one lying on a general position and the other on a twofold rotation axis. The dihedral angle between the two independent benzimidazole ring systems is 18.96 (5)°. In the crystal, molecules are linked into a three-dimensional network by O—H⋯O hydrogen bonding involving N-hydroxymethyl and carbonyl groups, and C—H⋯O hydrogen bonds.

Related literature

For general background to 2-benzimidazolones, see: Raghu et al. (2005 ); Porret & Hebermeier (1974 ); Habermeier (1976 ); Trask-Morrel et al. (1988 ); Hammach et al. (2006 ); Bansal et al. (1981 ). For related structures, see: Anklekar & Kulkarni (1995 ); Schwiebert et al. (1996 ). For the synthesis, see: Zinner & Spangenberg (1958 ).

Experimental

Crystal data

C₉H₁₀N₂O₃
M_r = 194.19
Monoclinic, C 2/c
a = 13.5515 (14) Å
b = 11.0848 (12) Å
c = 17.6253 (19) Å
β = 94.216 (2)°
V = 2640.4 (5) Å³
Z = 12
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 273 K
0.22 × 0.20 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.976, T_max = 0.986
13521 measured reflections
2684 independent reflections
2395 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.110
S = 1.10
2684 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O4	0.82	1.99	2.8003 (16)	169
O2—H2A⋯O5ⁱ	0.82	1.93	2.7503 (18)	176
O5—H5A⋯O3ⁱⁱ	0.82	1.84	2.6551 (17)	175
C3—H3⋯O2ⁱⁱⁱ	0.93	2.58	3.489 (2)	164
C14—H14B⋯O1ⁱⁱ	0.97	2.54	3.364 (2)	143
Symmetry codes: (i) $[x, -y+1, z-{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{3\over 2}}, -y+{\script{3\over 2}}, -z]$ .

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); 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 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536809040963/ci2925sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809040963/ci2925Isup2.hkl

checkCIF report

Comment top

1,3-Bishydroxyalkylated benzimidazolones are an important class of functionalized benzimidazoles which have been found to be useful as polymer intermediates (Raghu et al., 2005; Porret et al., 1974), fire retardants (Habermeier, 1976), and in curing process in textile industry (Trask-Morrel et al., 1988). Solid state chemistry of hydroxy methylated benzimidazole derivatives leading to thermal extrusion of formaldehyde has been reported (Anklekar et al., 1995) by our group. Design and synthesis of benzimidazolone p38 MAP kinase inhibitors (Hammach et al., 2006) is based on the analysis of their crystal structure data. Benzimidazolones have been reported to crystallize as hydrogen bonded molecular tapes (Schwiebert et al., 1996) which has been used to engineer structures of organic solids. In view of the therapeutic importance of aromatic and hetero aromatic compounds (Bansal et al., 1981) containing N-hydroxymethyl group, we report here the crystal structure of title compound.

The asymmetric unit of the title compound contains one and a half molecules, one lying on a general position and and the other on a twofold rotation axis (Fig.1). Atoms O4 and C13 lie on the twofold rotation axis. The two independent benzimidazole ring systems form a dihedral angle of 18.96 (5)°. There are no intramolecular hydrogen bonding between N-hydroxymethyl and carbonyl groups.

In the crystal, O—H···O hydrogen bonding involving N-hydroxymethyl and carbonyl groups results in the formation of three-dimensional network (Fig.2). In addition, C—H···O hydrogen bonds (Table 1) are observed. This type of intermolecular association is similar to that observed in the structure of benzimidazolone (Schwiebert et al., 1996).

Related literature top

For general background to 2-benzimidazolones, see: Raghu et al. (2005); Porret et al. (1974); Habermeier (1976); Trask-Morrel et al. (1988); Hammach et al. (2006); Bansal et al. (1981). For related structures, see: Anklekar et al. (1995); Schwiebert et al. (1996). For the synthesis, see: Zinner et al. (1958).

Experimental top

The title compound was prepared by following a literature method (Zinner et al., 1958). A mixture of 2-hydroxy benzimidazole (13.4 g, 0.01 M) and 37% formalin (30 ml, 1M) was refluxed for 30 minutes in presence of 100 ml water. The solid product formed was filtered and single crystals were grown by slow evaporation in water (yield 92%, m.p. 433 K). Spectral data IRν_CO = 1700 cm^-1, ν_OH = 3300 cm^-1. ¹H NMR -(CDCl₃+DMSO-d6)δ p.p.m. - 5.3(4H, d, CH₂) appeared as singlet on D₂O exchange, 6.2(2H, t, OH) vanished on D₂O exchange, 7.4–7.8 (4H, m, Ar-H). Mass m/z = 134 (100%).

Structure description top

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Packing of the molecules viewed down the b axis. Hydrogen bonds are shown as dashed lines.

1,3-Bis(hydroxymethyl)benzimidazolin-2-one top

Crystal data top

C₉H₁₀N₂O₃	F(000) = 1224
M_r = 194.19	D_x = 1.465 Mg m⁻³
Monoclinic, C2/c	Melting point: 433 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 13.5515 (14) Å	Cell parameters from 2684 reflections
b = 11.0848 (12) Å	θ = 2.3–26.4°
c = 17.6253 (19) Å	µ = 0.11 mm⁻¹
β = 94.216 (2)°	T = 273 K
V = 2640.4 (5) Å³	Plate, white
Z = 12	0.22 × 0.20 × 0.10 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2684 independent reflections
Radiation source: fine-focus sealed tube	2395 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ω and φ scans	θ_max = 26.4°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −16→16
T_min = 0.976, T_max = 0.986	k = −13→13
13521 measured reflections	l = −22→22

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) = 0.110	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0486P)² + 1.5821P] where P = (F_o² + 2F_c²)/3
2684 reflections	(Δ/σ)_max = 0.001
191 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₉H₁₀N₂O₃	V = 2640.4 (5) Å³
M_r = 194.19	Z = 12
Monoclinic, C2/c	Mo Kα radiation
a = 13.5515 (14) Å	µ = 0.11 mm⁻¹
b = 11.0848 (12) Å	T = 273 K
c = 17.6253 (19) Å	0.22 × 0.20 × 0.10 mm
β = 94.216 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2684 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	2395 reflections with I > 2σ(I)
T_min = 0.976, T_max = 0.986	R_int = 0.025
13521 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.110	H-atom parameters constrained
S = 1.10	Δρ_max = 0.16 e Å⁻³
2684 reflections	Δρ_min = −0.24 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
O1	0.36019 (9)	0.44213 (11)	0.19000 (7)	0.0555 (3)
H1A	0.4009	0.3984	0.2131	0.083*
O2	0.51268 (9)	0.85515 (11)	−0.04107 (7)	0.0560 (3)
H2A	0.4597	0.8565	−0.0667	0.084*
O3	0.32846 (8)	0.69395 (11)	0.07135 (7)	0.0525 (3)
N1	0.44553 (9)	0.54147 (11)	0.09507 (7)	0.0390 (3)
N2	0.49663 (9)	0.72131 (11)	0.06132 (7)	0.0420 (3)
C1	0.61458 (12)	0.44272 (15)	0.11034 (9)	0.0469 (4)
H1	0.5932	0.3665	0.1238	0.056*
C2	0.71420 (13)	0.46756 (18)	0.10526 (10)	0.0568 (5)
H2	0.7604	0.4063	0.1146	0.068*
C3	0.74639 (13)	0.5819 (2)	0.08647 (10)	0.0582 (5)
H3	0.8138	0.5963	0.0847	0.070*
C4	0.67978 (12)	0.67501 (17)	0.07028 (9)	0.0499 (4)
H4	0.7012	0.7516	0.0576	0.060*
C5	0.58057 (11)	0.64950 (13)	0.07380 (8)	0.0388 (3)
C6	0.54853 (11)	0.53545 (13)	0.09463 (8)	0.0372 (3)
C7	0.41401 (11)	0.65604 (14)	0.07545 (8)	0.0398 (3)
C8	0.49544 (14)	0.84582 (14)	0.03582 (10)	0.0511 (4)
H8A	0.4317	0.8813	0.0440	0.061*
H8B	0.5458	0.8909	0.0658	0.061*
C9	0.37880 (12)	0.44495 (14)	0.11304 (9)	0.0456 (4)
H9A	0.3166	0.4549	0.0827	0.055*
H9B	0.4072	0.3684	0.0993	0.055*
O4	0.5000	0.27510 (13)	0.2500	0.0467 (4)
O5	0.33811 (9)	0.12882 (13)	0.36950 (7)	0.0628 (4)
H5A	0.2848	0.1462	0.3858	0.094*
N3	0.42148 (9)	0.09011 (11)	0.26254 (7)	0.0396 (3)
C10	0.45046 (15)	−0.24348 (15)	0.25741 (9)	0.0553 (5)
H10	0.4179	−0.3167	0.2617	0.066*
C11	0.39872 (13)	−0.13699 (15)	0.26601 (9)	0.0487 (4)
H11	0.3325	−0.1370	0.2765	0.058*
C12	0.45049 (11)	−0.03066 (13)	0.25817 (8)	0.0385 (3)
C13	0.5000	0.16353 (19)	0.2500	0.0379 (4)
C14	0.32941 (11)	0.13248 (16)	0.28957 (9)	0.0468 (4)
H14A	0.3162	0.2143	0.2722	0.056*
H14B	0.2752	0.0814	0.2701	0.056*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0523 (7)	0.0567 (7)	0.0602 (7)	0.0107 (6)	0.0216 (5)	0.0184 (6)
O2	0.0488 (7)	0.0629 (8)	0.0571 (7)	0.0001 (6)	0.0090 (5)	0.0226 (6)
O3	0.0415 (6)	0.0568 (7)	0.0603 (7)	0.0122 (5)	0.0109 (5)	0.0124 (5)
N1	0.0370 (6)	0.0371 (6)	0.0436 (7)	0.0016 (5)	0.0077 (5)	0.0042 (5)
N2	0.0454 (7)	0.0366 (7)	0.0451 (7)	0.0036 (5)	0.0122 (5)	0.0077 (5)
C1	0.0514 (9)	0.0423 (8)	0.0477 (9)	0.0097 (7)	0.0092 (7)	0.0043 (7)
C2	0.0463 (10)	0.0675 (12)	0.0574 (10)	0.0190 (8)	0.0094 (8)	0.0066 (9)
C3	0.0382 (9)	0.0814 (13)	0.0561 (10)	0.0022 (8)	0.0110 (7)	0.0020 (9)
C4	0.0479 (9)	0.0547 (10)	0.0486 (9)	−0.0070 (7)	0.0143 (7)	0.0017 (7)
C5	0.0424 (8)	0.0402 (8)	0.0349 (7)	0.0031 (6)	0.0095 (6)	0.0012 (6)
C6	0.0392 (8)	0.0397 (8)	0.0335 (7)	0.0020 (6)	0.0079 (5)	−0.0001 (6)
C7	0.0419 (8)	0.0417 (8)	0.0366 (7)	0.0048 (6)	0.0084 (6)	0.0045 (6)
C8	0.0629 (11)	0.0366 (8)	0.0547 (10)	0.0025 (7)	0.0103 (8)	0.0081 (7)
C9	0.0437 (8)	0.0404 (8)	0.0528 (9)	−0.0040 (7)	0.0052 (7)	0.0027 (7)
O4	0.0426 (8)	0.0344 (8)	0.0635 (10)	0.000	0.0068 (7)	0.000
O5	0.0400 (6)	0.0918 (10)	0.0575 (7)	0.0004 (6)	0.0105 (5)	−0.0143 (7)
N3	0.0328 (6)	0.0377 (7)	0.0490 (7)	−0.0017 (5)	0.0069 (5)	−0.0008 (5)
C10	0.0860 (13)	0.0370 (8)	0.0426 (9)	−0.0116 (8)	0.0021 (8)	0.0014 (7)
C11	0.0562 (10)	0.0459 (9)	0.0439 (8)	−0.0124 (7)	0.0032 (7)	0.0019 (7)
C12	0.0416 (8)	0.0376 (8)	0.0363 (7)	−0.0008 (6)	0.0020 (6)	0.0000 (6)
C13	0.0346 (10)	0.0381 (11)	0.0410 (11)	0.000	0.0025 (8)	0.000
C14	0.0329 (8)	0.0504 (9)	0.0575 (10)	0.0001 (7)	0.0052 (6)	−0.0001 (7)

Geometric parameters (Å, º) top

O1—C9	1.3981 (19)	C5—C6	1.395 (2)
O1—H1A	0.82	C8—H8A	0.97
O2—C8	1.396 (2)	C8—H8B	0.97
O2—H2A	0.82	C9—H9A	0.97
O3—C7	1.2304 (18)	C9—H9B	0.97
N1—C7	1.3759 (19)	O4—C13	1.237 (3)
N1—C6	1.3980 (19)	O5—C14	1.406 (2)
N1—C9	1.4509 (19)	O5—H5A	0.82
N2—C7	1.371 (2)	N3—C13	1.3704 (17)
N2—C5	1.3925 (19)	N3—C12	1.3990 (19)
N2—C8	1.451 (2)	N3—C14	1.4462 (19)
C1—C6	1.378 (2)	C10—C10ⁱ	1.387 (4)
C1—C2	1.387 (2)	C10—C11	1.387 (3)
C1—H1	0.93	C11—C12	1.384 (2)
C2—C3	1.388 (3)	C11—H11	0.93
C2—H2	0.93	C12—C12ⁱ	1.393 (3)
C3—C4	1.387 (3)	C13—N3ⁱ	1.3704 (17)
C3—H3	0.93	C14—H14A	0.97
C4—C5	1.380 (2)	C14—H14B	0.97
C4—H4	0.93

C9—O1—H1A	109.4	O2—C8—H8B	109.2
C8—O2—H2A	109.5	N2—C8—H8B	109.2
C7—N1—C6	109.53 (12)	H8A—C8—H8B	107.9
C7—N1—C9	123.27 (13)	O1—C9—N1	112.84 (13)
C6—N1—C9	127.20 (12)	O1—C9—H9A	109.0
C7—N2—C5	109.76 (12)	N1—C9—H9A	109.0
C7—N2—C8	124.58 (14)	O1—C9—H9B	109.0
C5—N2—C8	125.66 (13)	N1—C9—H9B	109.0
C6—C1—C2	117.39 (16)	H9A—C9—H9B	107.8
C6—C1—H1	121.3	C14—O5—H5A	109.5
C2—C1—H1	121.3	C13—N3—C12	109.55 (12)
C1—C2—C3	121.40 (16)	C13—N3—C14	124.00 (13)
C1—C2—H2	119.3	C12—N3—C14	125.57 (13)
C3—C2—H2	119.3	C10ⁱ—C10—C11	121.66 (10)
C4—C3—C2	121.16 (16)	C10ⁱ—C10—H10	119.2
C4—C3—H3	119.4	C11—C10—H10	119.2
C2—C3—H3	119.4	C12—C11—C10	116.74 (16)
C5—C4—C3	117.36 (16)	C12—C11—H11	121.6
C5—C4—H4	121.3	C10—C11—H11	121.6
C3—C4—H4	121.3	C11—C12—C12ⁱ	121.59 (10)
C4—C5—N2	131.54 (15)	C11—C12—N3	131.53 (14)
C4—C5—C6	121.39 (14)	C12ⁱ—C12—N3	106.88 (8)
N2—C5—C6	107.05 (13)	O4—C13—N3	126.43 (9)
C1—C6—C5	121.26 (14)	O4—C13—N3ⁱ	126.43 (9)
C1—C6—N1	131.97 (14)	N3—C13—N3ⁱ	107.14 (18)
C5—C6—N1	106.76 (12)	O5—C14—N3	108.05 (13)
O3—C7—N2	125.99 (14)	O5—C14—H14A	110.1
O3—C7—N1	127.14 (14)	N3—C14—H14A	110.1
N2—C7—N1	106.87 (12)	O5—C14—H14B	110.1
O2—C8—N2	111.86 (14)	N3—C14—H14B	110.1
O2—C8—H8A	109.2	H14A—C14—H14B	108.4
N2—C8—H8A	109.2

C6—C1—C2—C3	1.2 (3)	C8—N2—C7—N1	177.40 (14)
C1—C2—C3—C4	−1.5 (3)	C6—N1—C7—O3	−178.71 (15)
C2—C3—C4—C5	0.1 (3)	C9—N1—C7—O3	1.2 (2)
C3—C4—C5—N2	179.76 (16)	C6—N1—C7—N2	1.10 (16)
C3—C4—C5—C6	1.6 (2)	C9—N1—C7—N2	−178.97 (13)
C7—N2—C5—C4	−177.04 (16)	C7—N2—C8—O2	−105.28 (17)
C8—N2—C5—C4	4.1 (3)	C5—N2—C8—O2	73.5 (2)
C7—N2—C5—C6	1.36 (16)	C7—N1—C9—O1	−88.27 (17)
C8—N2—C5—C6	−177.55 (14)	C6—N1—C9—O1	91.64 (17)
C2—C1—C6—C5	0.5 (2)	C10ⁱ—C10—C11—C12	0.8 (3)
C2—C1—C6—N1	−179.32 (15)	C10—C11—C12—C12ⁱ	0.5 (3)
C4—C5—C6—C1	−1.9 (2)	C10—C11—C12—N3	179.38 (15)
N2—C5—C6—C1	179.46 (14)	C13—N3—C12—C11	−179.51 (14)
C4—C5—C6—N1	177.94 (13)	C14—N3—C12—C11	10.9 (3)
N2—C5—C6—N1	−0.65 (16)	C13—N3—C12—C12ⁱ	−0.50 (18)
C7—N1—C6—C1	179.60 (16)	C14—N3—C12—C12ⁱ	−170.07 (15)
C9—N1—C6—C1	−0.3 (3)	C12—N3—C13—O4	−179.81 (7)
C7—N1—C6—C5	−0.27 (16)	C14—N3—C13—O4	−10.04 (16)
C9—N1—C6—C5	179.81 (14)	C12—N3—C13—N3ⁱ	0.19 (7)
C5—N2—C7—O3	178.30 (15)	C14—N3—C13—N3ⁱ	169.96 (16)
C8—N2—C7—O3	−2.8 (2)	C13—N3—C14—O5	−89.75 (16)
C5—N2—C7—N1	−1.52 (16)	C12—N3—C14—O5	78.38 (18)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O4	0.82	1.99	2.8003 (16)	169
O2—H2A···O5ⁱⁱ	0.82	1.93	2.7503 (18)	176
O5—H5A···O3ⁱⁱⁱ	0.82	1.84	2.6551 (17)	175
C3—H3···O2^iv	0.93	2.58	3.489 (2)	164
C14—H14B···O1ⁱⁱⁱ	0.97	2.54	3.364 (2)	143

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

Experimental details

Crystal data
Chemical formula	C₉H₁₀N₂O₃
M_r	194.19
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	273
a, b, c (Å)	13.5515 (14), 11.0848 (12), 17.6253 (19)
β (°)	94.216 (2)
V (Å³)	2640.4 (5)
Z	12
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.22 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.976, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	13521, 2684, 2395
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.110, 1.10
No. of reflections	2684
No. of parameters	191
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.24

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O4	0.82	1.99	2.8003 (16)	169
O2—H2A···O5ⁱ	0.82	1.93	2.7503 (18)	176
O5—H5A···O3ⁱⁱ	0.82	1.84	2.6551 (17)	175
C3—H3···O2ⁱⁱⁱ	0.93	2.58	3.489 (2)	164
C14—H14B···O1ⁱⁱ	0.97	2.54	3.364 (2)	143

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

Acknowledgements

The authors thank Professor T. N. Guru Row and Miss Brinda Selvaraj, Solid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore, for their help with the data collection.

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