4-[1-(4-Hy­droxy-3-meth­oxy­benz­yl)-1H-benzimidazol-2-yl]-2-meth­oxy­phenol

Xiao, Z.; Gao, T.; Huang, F.; Jiang, T.

doi:10.1107/S1600536811043935

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o3087

doi:10.1107/S1600536811043935

Open

access

4-[1-(4-Hydroxy-3-methoxybenzyl)-1H-benzimidazol-2-yl]-2-methoxyphenol

Zuo-an Xiao,^a ^* Tao Gao,^a Fa-jun Huang ^a and Ting-ting Jiang ^a

^aSchool of Chemical Engineering and Food Science, Xiangfan University, Xiangfan 441053, People's Republic of China
^*Correspondence e-mail: blueice8250@yahoo.com.cn

(Received 17 October 2011; accepted 23 October 2011; online 29 October 2011)

In the title molecule, C₂₂H₂₀N₂O₄, the dihedral angles between the benzimidazole ring system and the benzene rings are 44.26 (2) and 82.91 (2)°. Intramolecular O—H⋯O hydrogen bonds occur. In the crystal, O—H⋯N and O—H⋯O hydrogen bonds connect the molecules into a two-dimension network parallel to (10 $[\overline{2}]$ ) and weak intermolecular C—H⋯O hydrogen bonds complete the formation of a three-dimensional network.

Related literature

For the biological appications of benzimidazole compounds, see: Santoro et al. (2000 ); Sundberg et al. (1977 ). For related structures, see: Li et al. (2005 ); Liu et al. (2003 ); Xi et al. (2006 ).

Experimental

Crystal data

C₂₂H₂₀N₂O₄
M_r = 376.40
Monoclinic, P 2₁ /c
a = 7.9717 (9) Å
b = 16.4327 (19) Å
c = 14.3560 (16) Å
β = 95.133 (2)°
V = 1873.0 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.966, T_max = 0.983
14067 measured reflections
4625 independent reflections
3718 reflections with I > 2σ(I)
R_int = 0.064

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.154
S = 1.06
4625 reflections
261 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4A⋯O3	0.89 (2)	2.25 (2)	2.6598 (18)	108.0 (18)
O1—H1A⋯O2	0.85 (3)	2.22 (3)	2.6631 (18)	113 (2)
O4—H4A⋯N2ⁱ	0.89 (2)	1.90 (2)	2.7671 (18)	165 (2)
O1—H1A⋯O4ⁱⁱ	0.85 (3)	2.07 (3)	2.7934 (17)	143 (2)
C15—H15B⋯O4ⁱⁱⁱ	0.97	2.59	3.402 (2)	141
Symmetry codes: (i) $[x+1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811043935/lh5356sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811043935/lh5356Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811043935/lh5356Isup3.cml

checkCIF report

Comment top

Benzimidazole is a common species in biological and biochemical structures (Sundberg et al., 1977; Santoro et al., 2000). Many benzimidazole derivatives have already been reported (e.g. Liu et al., 2003; Li et al., 2005; Xi et al., 2006) and the preparation of the title compound, (I), is part of our effort to contribute to this research. Herein we report the crystal structure of (I).

In the molecule (Fig. 1) the dihedral angles between the benzimidazole ring system and the benzene rings are [C8-C13] 44.26 (2)° and [C16-C21] 82.91 (2)°. All bond lengths and bond angles are as expected. In the crystal, (Fig.2) molecules are linked by O—H···N and O—H···O and weak C—H···O hydrogen bonds to form a three-dimensional network.

Related literature top

For the biological appications of benzimidazole compounds, see: Santoro et al. (2000); Sundberg et al. (1977). For related structures, see: Li et al. (2005); Liu et al. (2003); Xi et al. (2006).

Experimental top

3-Methoxy-4-hydroxyphenyl formaldehyde (10 mmol) and 1,2-diaminobenzene(5 mmol) were mixed in hot water (333 K), the resulting mixture was stirred and refluxed for 3 h at 333 K. The solution was filtered, and the resulting yellow precipitate was recystallized from methanol to obtain pure product. Yellow crystals suitable for an X-ray diffraction study were obtained by slow evaporation of methanol and dimethyl sulfoxide (1:1 v/v) for two months.

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: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Part of the crystal structure with hydrogen bonds shown as dashed lines.

4-[1-(4-Hydroxy-3-methoxybenzyl)-1H-benzimidazol-2-yl]-2-methoxyphenol top

Crystal data top

C₂₂H₂₀N₂O₄	F(000) = 792
M_r = 376.40	D_x = 1.335 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5118 reflections
a = 7.9717 (9) Å	θ = 2.5–27.7°
b = 16.4327 (19) Å	µ = 0.09 mm⁻¹
c = 14.3560 (16) Å	T = 298 K
β = 95.133 (2)°	Block, yellow
V = 1873.0 (4) Å³	0.20 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	4625 independent reflections
Radiation source: fine-focus sealed tube	3718 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.064
ϕ and ω scans	θ_max = 28.3°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→9
T_min = 0.966, T_max = 0.983	k = −21→21
14067 measured reflections	l = −17→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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.154	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0713P)² + 0.3997P] where P = (F_o² + 2F_c²)/3
4625 reflections	(Δ/σ)_max = 0.001
261 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₂H₂₀N₂O₄	V = 1873.0 (4) Å³
M_r = 376.40	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.9717 (9) Å	µ = 0.09 mm⁻¹
b = 16.4327 (19) Å	T = 298 K
c = 14.3560 (16) Å	0.20 × 0.20 × 0.20 mm
β = 95.133 (2)°

Data collection top

Bruker SMART CCD diffractometer	4625 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3718 reflections with I > 2σ(I)
T_min = 0.966, T_max = 0.983	R_int = 0.064
14067 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.154	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.30 e Å⁻³
4625 reflections	Δρ_min = −0.23 e Å⁻³
261 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	0.6594 (2)	0.37261 (10)	0.41671 (11)	0.0434 (4)
C2	0.4947 (2)	0.34793 (10)	0.39288 (11)	0.0402 (4)
C3	0.3707 (3)	0.40430 (12)	0.36173 (13)	0.0558 (5)
H3	0.2600	0.3884	0.3457	0.067*
C4	0.4192 (4)	0.48403 (13)	0.35583 (16)	0.0709 (7)
H4	0.3397	0.5228	0.3348	0.085*
C5	0.5838 (4)	0.50832 (13)	0.38041 (17)	0.0763 (7)
H5	0.6112	0.5631	0.3757	0.092*
C6	0.7085 (3)	0.45372 (12)	0.41172 (15)	0.0635 (6)
H6	0.8186	0.4702	0.4285	0.076*
C7	0.63537 (19)	0.23907 (9)	0.43023 (10)	0.0346 (3)
C8	0.67801 (19)	0.15292 (9)	0.44647 (10)	0.0358 (3)
C9	0.6102 (2)	0.09509 (10)	0.38356 (11)	0.0414 (4)
H9	0.5444	0.1114	0.3301	0.050*
C10	0.6401 (2)	0.01332 (10)	0.40007 (12)	0.0448 (4)
H10	0.5953	−0.0251	0.3572	0.054*
C11	0.7358 (2)	−0.01188 (10)	0.47960 (11)	0.0398 (4)
C12	0.8042 (2)	0.04607 (10)	0.54392 (11)	0.0378 (4)
C13	0.7768 (2)	0.12775 (10)	0.52693 (11)	0.0380 (4)
H13	0.8239	0.1662	0.5690	0.046*
C14	0.9622 (3)	0.06781 (14)	0.69039 (15)	0.0690 (6)
H14A	1.0387	0.1045	0.6640	0.104*
H14B	1.0213	0.0374	0.7402	0.104*
H14C	0.8729	0.0983	0.7145	0.104*
C15	0.9316 (2)	0.29712 (12)	0.45926 (12)	0.0464 (4)
H15A	0.9819	0.3390	0.4232	0.056*
H15B	0.9686	0.2449	0.4371	0.056*
C16	0.9974 (2)	0.30661 (9)	0.56100 (11)	0.0378 (4)
C17	1.1623 (2)	0.28316 (10)	0.58622 (11)	0.0388 (4)
H17	1.2285	0.2639	0.5409	0.047*
C18	1.2289 (2)	0.28829 (10)	0.67832 (11)	0.0378 (3)
C19	1.1305 (2)	0.31602 (9)	0.74762 (11)	0.0366 (3)
C20	0.9677 (2)	0.34072 (12)	0.72206 (12)	0.0474 (4)
H20	0.9015	0.3604	0.7672	0.057*
C21	0.9017 (2)	0.33641 (12)	0.62925 (13)	0.0480 (4)
H21	0.7920	0.3538	0.6128	0.058*
C22	1.4913 (2)	0.22847 (16)	0.65140 (15)	0.0648 (6)
H22A	1.4335	0.1811	0.6261	0.097*
H22B	1.5945	0.2124	0.6861	0.097*
H22C	1.5159	0.2640	0.6013	0.097*
N1	0.74880 (17)	0.30206 (8)	0.44092 (10)	0.0397 (3)
N2	0.48213 (17)	0.26436 (8)	0.40272 (9)	0.0383 (3)
O1	0.76267 (19)	−0.09254 (7)	0.49438 (9)	0.0544 (4)
H1A	0.804 (3)	−0.1004 (16)	0.550 (2)	0.082*
O2	0.89395 (17)	0.01375 (7)	0.62064 (9)	0.0531 (3)
O3	1.38974 (16)	0.26905 (11)	0.71051 (9)	0.0636 (4)
O4	1.19250 (16)	0.31888 (8)	0.83918 (8)	0.0454 (3)
H4A	1.291 (3)	0.2940 (14)	0.8496 (17)	0.068*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0577 (10)	0.0391 (9)	0.0322 (8)	0.0003 (7)	−0.0019 (7)	−0.0008 (6)
C2	0.0504 (9)	0.0387 (8)	0.0303 (7)	0.0052 (7)	−0.0021 (6)	−0.0002 (6)
C3	0.0647 (12)	0.0525 (11)	0.0487 (10)	0.0180 (9)	−0.0039 (9)	0.0068 (8)
C4	0.1036 (19)	0.0459 (11)	0.0609 (13)	0.0260 (12)	−0.0050 (12)	0.0066 (9)
C5	0.128 (2)	0.0345 (10)	0.0656 (14)	0.0008 (12)	0.0037 (14)	0.0063 (9)
C6	0.0835 (15)	0.0465 (11)	0.0597 (12)	−0.0137 (10)	0.0017 (11)	−0.0027 (9)
C7	0.0386 (8)	0.0384 (8)	0.0260 (7)	0.0014 (6)	−0.0018 (6)	−0.0012 (6)
C8	0.0375 (8)	0.0373 (8)	0.0319 (7)	0.0048 (6)	−0.0003 (6)	0.0000 (6)
C9	0.0462 (9)	0.0437 (9)	0.0324 (8)	0.0032 (7)	−0.0064 (6)	0.0004 (6)
C10	0.0551 (10)	0.0415 (9)	0.0362 (8)	−0.0009 (7)	−0.0046 (7)	−0.0055 (7)
C11	0.0469 (9)	0.0351 (8)	0.0375 (8)	0.0044 (7)	0.0043 (7)	0.0005 (6)
C12	0.0388 (8)	0.0420 (8)	0.0317 (8)	0.0055 (6)	−0.0017 (6)	0.0027 (6)
C13	0.0409 (9)	0.0385 (8)	0.0337 (8)	0.0038 (6)	−0.0030 (6)	−0.0031 (6)
C14	0.0909 (16)	0.0644 (13)	0.0461 (11)	0.0108 (11)	−0.0258 (11)	0.0005 (9)
C15	0.0391 (9)	0.0624 (11)	0.0371 (9)	−0.0039 (7)	0.0004 (7)	−0.0058 (8)
C16	0.0365 (8)	0.0377 (8)	0.0382 (8)	−0.0044 (6)	−0.0021 (6)	−0.0050 (6)
C17	0.0375 (8)	0.0442 (9)	0.0349 (8)	−0.0002 (7)	0.0043 (6)	−0.0060 (6)
C18	0.0344 (8)	0.0421 (8)	0.0365 (8)	0.0009 (6)	0.0006 (6)	−0.0033 (6)
C19	0.0401 (8)	0.0342 (8)	0.0353 (8)	−0.0015 (6)	0.0018 (6)	−0.0065 (6)
C20	0.0415 (9)	0.0594 (11)	0.0414 (9)	0.0091 (8)	0.0049 (7)	−0.0131 (8)
C21	0.0344 (8)	0.0615 (11)	0.0469 (10)	0.0080 (8)	−0.0029 (7)	−0.0096 (8)
C22	0.0434 (11)	0.0933 (16)	0.0573 (12)	0.0176 (10)	0.0016 (9)	−0.0170 (11)
N1	0.0397 (7)	0.0421 (7)	0.0359 (7)	−0.0014 (5)	−0.0052 (5)	−0.0024 (5)
N2	0.0401 (7)	0.0391 (7)	0.0341 (7)	0.0040 (5)	−0.0048 (5)	0.0033 (5)
O1	0.0800 (10)	0.0352 (6)	0.0460 (7)	0.0036 (6)	−0.0051 (7)	0.0024 (5)
O2	0.0673 (8)	0.0450 (7)	0.0432 (7)	0.0066 (6)	−0.0160 (6)	0.0057 (5)
O3	0.0439 (7)	0.1088 (12)	0.0369 (7)	0.0244 (7)	−0.0025 (5)	−0.0126 (7)
O4	0.0447 (7)	0.0573 (8)	0.0335 (6)	0.0082 (5)	0.0000 (5)	−0.0089 (5)

Geometric parameters (Å, º) top

C1—C2	1.388 (2)	C14—O2	1.411 (2)
C1—N1	1.389 (2)	C14—H14A	0.9600
C1—C6	1.393 (3)	C14—H14B	0.9600
C2—N2	1.385 (2)	C14—H14C	0.9600
C2—C3	1.398 (2)	C15—N1	1.460 (2)
C3—C4	1.371 (3)	C15—C16	1.515 (2)
C3—H3	0.9300	C15—H15A	0.9700
C4—C5	1.386 (4)	C15—H15B	0.9700
C4—H4	0.9300	C16—C21	1.384 (2)
C5—C6	1.384 (3)	C16—C17	1.386 (2)
C5—H5	0.9300	C17—C18	1.383 (2)
C6—H6	0.9300	C17—H17	0.9300
C7—N2	1.3171 (19)	C18—O3	1.361 (2)
C7—N1	1.374 (2)	C18—C19	1.397 (2)
C7—C8	1.470 (2)	C19—O4	1.3630 (19)
C8—C9	1.387 (2)	C19—C20	1.378 (2)
C8—C13	1.401 (2)	C20—C21	1.390 (2)
C9—C10	1.381 (2)	C20—H20	0.9300
C9—H9	0.9300	C21—H21	0.9300
C10—C11	1.379 (2)	C22—O3	1.394 (2)
C10—H10	0.9300	C22—H22A	0.9600
C11—O1	1.3564 (19)	C22—H22B	0.9600
C11—C12	1.402 (2)	C22—H22C	0.9600
C12—O2	1.3659 (18)	O1—H1A	0.85 (3)
C12—C13	1.378 (2)	O4—H4A	0.89 (2)
C13—H13	0.9300

C2—C1—N1	105.72 (14)	O2—C14—H14C	109.5
C2—C1—C6	122.08 (17)	H14A—C14—H14C	109.5
N1—C1—C6	132.19 (18)	H14B—C14—H14C	109.5
N2—C2—C1	109.87 (14)	N1—C15—C16	114.96 (14)
N2—C2—C3	129.36 (17)	N1—C15—H15A	108.5
C1—C2—C3	120.74 (17)	C16—C15—H15A	108.5
C4—C3—C2	117.3 (2)	N1—C15—H15B	108.5
C4—C3—H3	121.4	C16—C15—H15B	108.5
C2—C3—H3	121.4	H15A—C15—H15B	107.5
C3—C4—C5	121.7 (2)	C21—C16—C17	118.88 (15)
C3—C4—H4	119.2	C21—C16—C15	123.63 (15)
C5—C4—H4	119.2	C17—C16—C15	117.49 (15)
C6—C5—C4	122.1 (2)	C18—C17—C16	120.46 (15)
C6—C5—H5	118.9	C18—C17—H17	119.8
C4—C5—H5	118.9	C16—C17—H17	119.8
C5—C6—C1	116.1 (2)	O3—C18—C17	125.46 (15)
C5—C6—H6	121.9	O3—C18—C19	113.94 (14)
C1—C6—H6	121.9	C17—C18—C19	120.59 (14)
N2—C7—N1	112.29 (14)	O4—C19—C20	119.87 (15)
N2—C7—C8	123.14 (14)	O4—C19—C18	121.33 (14)
N1—C7—C8	124.57 (14)	C20—C19—C18	118.80 (15)
C9—C8—C13	119.48 (15)	C19—C20—C21	120.45 (16)
C9—C8—C7	119.06 (13)	C19—C20—H20	119.8
C13—C8—C7	121.35 (14)	C21—C20—H20	119.8
C10—C9—C8	120.24 (14)	C16—C21—C20	120.77 (15)
C10—C9—H9	119.9	C16—C21—H21	119.6
C8—C9—H9	119.9	C20—C21—H21	119.6
C11—C10—C9	120.55 (15)	O3—C22—H22A	109.5
C11—C10—H10	119.7	O3—C22—H22B	109.5
C9—C10—H10	119.7	H22A—C22—H22B	109.5
O1—C11—C10	119.40 (15)	O3—C22—H22C	109.5
O1—C11—C12	120.92 (14)	H22A—C22—H22C	109.5
C10—C11—C12	119.67 (15)	H22B—C22—H22C	109.5
O2—C12—C13	125.79 (14)	C7—N1—C1	106.44 (13)
O2—C12—C11	114.31 (14)	C7—N1—C15	127.93 (14)
C13—C12—C11	119.90 (14)	C1—N1—C15	124.98 (14)
C12—C13—C8	120.15 (14)	C7—N2—C2	105.67 (13)
C12—C13—H13	119.9	C11—O1—H1A	109.8 (18)
C8—C13—H13	119.9	C12—O2—C14	117.93 (14)
O2—C14—H14A	109.5	C18—O3—C22	119.05 (14)
O2—C14—H14B	109.5	C19—O4—H4A	112.7 (16)
H14A—C14—H14B	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4A···O3	0.89 (2)	2.25 (2)	2.6598 (18)	108.0 (18)
O1—H1A···O2	0.85 (3)	2.22 (3)	2.6631 (18)	113 (2)
O4—H4A···N2ⁱ	0.89 (2)	1.90 (2)	2.7671 (18)	165 (2)
O1—H1A···O4ⁱⁱ	0.85 (3)	2.07 (3)	2.7934 (17)	143 (2)
C15—H15B···O4ⁱⁱⁱ	0.97	2.59	3.402 (2)	141

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

Experimental details

Crystal data
Chemical formula	C₂₂H₂₀N₂O₄
M_r	376.40
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	7.9717 (9), 16.4327 (19), 14.3560 (16)
β (°)	95.133 (2)
V (Å³)	1873.0 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.966, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	14067, 4625, 3718
R_int	0.064
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.154, 1.06
No. of reflections	4625
No. of parameters	261
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.23

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4A···O3	0.89 (2)	2.25 (2)	2.6598 (18)	108.0 (18)
O1—H1A···O2	0.85 (3)	2.22 (3)	2.6631 (18)	113 (2)
O4—H4A···N2ⁱ	0.89 (2)	1.90 (2)	2.7671 (18)	165 (2)
O1—H1A···O4ⁱⁱ	0.85 (3)	2.07 (3)	2.7934 (17)	143 (2)
C15—H15B···O4ⁱⁱⁱ	0.97	2.59	3.402 (2)	141.3

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

Acknowledgements

The authors are grateful to the Science Technology Research Programme of the Education Office of Hubei Province (grant No. Q20092503) for financial support.

References

Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Li, J., Meng, X.-G. & Liao, Z.-R. (2005). Acta Cryst. E61, o3421–o3423. Web of Science CSD CrossRef IUCr Journals Google Scholar
Liu, Y.-C., Ma, J.-F., Hu, N.-H. & Jia, H.-Q. (2003). Acta Cryst. E59, m361–m363. Web of Science CSD CrossRef IUCr Journals Google Scholar
Santoro, S. W., Joyce, G. F., Sakthivel, K., Gramatikova, S. & Barbas, C. F. (2000). J. Am. Chem. Soc. 122, 2433–2439. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sundberg, R. J., Yilmaz, I. & Mente, D. C. (1977). Inorg. Chem. 16, 1470–1476. CSD CrossRef CAS Web of Science Google Scholar
Xi, Y., Jiang, M., Li, J., Wang, C., Yan, J.-F. & Zhang, F.-X. (2006). Acta Chim. Sin. 64, 1183–1188. CAS Google Scholar