N′-(2-Chloro­benzyl­idene)-3,4,5-tri­methoxy­benzohydrazide methanol solvate

He, D.-H.; Zhu, Y.-C.; Yang, Z.-R.; Song, S.-Y.; Chen, Q.-J.

doi:10.1107/S1600536808023891

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1649

doi:10.1107/S1600536808023891

Open

access

N′-(2-Chlorobenzylidene)-3,4,5-trimethoxybenzohydrazide methanol solvate

Dao-Hang He,^a ^* Yong-Chuang Zhu,^a Zhuo-Ru Yang,^a Shao-Yun Song ^b and Qi-Jin Chen ^b

^aSchool of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, People's Republic of China, and ^bCollege of Life Sciences, Sun Yat-sen University, Guangzhou 510275, People's Republic of China
^*Correspondence e-mail: daohanghe@yahoo.com.cn

(Received 8 July 2008; accepted 28 July 2008; online 31 July 2008)

In the title compound, C₁₇H₁₇ClN₂O₄·CH₄O, the dihedral angle between the benzene ring planes is 5.29 (6)°. Intermolecular N—H⋯O and O—H⋯O hydrogen bonds link the molecules into a chain along the a axis.

Related literature

For related literature, see: Allen et al. (1987 ), Bernardino et al. (2006 ); Ganjali et al. (2006 ); Gardner et al. (1991 ); Patole et al. (2003 )

Experimental

Crystal data

C₁₇H₁₇ClN₂O₄·CH₄O
M_r = 380.82
Orthorhombic, P n a 2₁
a = 12.9356 (7) Å
b = 4.8718 (3) Å
c = 29.4119 (16) Å
V = 1853.53 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 173 (2) K
0.48 × 0.40 × 0.39 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.895, T_max = 0.913
9008 measured reflections
3916 independent reflections
3561 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.080
S = 1.09
3916 reflections
240 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.17 e Å⁻³
Absolute structure: Flack (1983 ), 1846 Friedel pairs
Flack parameter: 0.04 (5)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O5ⁱ	0.88	2.01	2.8673 (19)	165
O5—H5⋯O4	0.84	1.97	2.7904 (18)	166
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ .

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT-Plus (Bruker, 2003 ); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536808023891/hb2761sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808023891/hb2761Isup2.hkl

checkCIF report

Comment top

Molecules involving Schiff bases have attracted much attention due to their diverse range of bioactivities in pharmaceutical and agrochemical field (e.g. Bernardino et al., 2006; Ganjali et al., 2006). We now report the synthesis and structure of the title compound, (I), obtained by the condensation of 3,4,5-trimethoxybenzohydrazide with 2-chlorobenzaldehyde as a methanol solvate (Fig. 1).

The bond lengths and bond angles for (I) are within normal ranges (Allen et al., 1987). The two benzene rings are approximately planar, with a dihedral angle of 5.29 (6)°. The methanol molecules in the crystal are lined to the Schiff base moieties through intermolecular N—H···O and O—H···O hydrogen bonds to form a chain along the a axis, which helps to consolidate the packing (Fig 2).

Related literature top

For related literature, see: Allen et al. (1987), Bernardino et al. (2006); Ganjali et al. (2006); Gardner et al. (1991); Patole et al. (2003)

Experimental top

A mixture of 3,4,5-trimethoxybenzohydrazide (1 mmol) and 2-chlorobenzaldehyde in anhydrous ethanol (10 ml) was refluxed for 2 h. When the solution was cooled to room temperature, some white needles separated out. After filtration, colorless blocks of (I) were obtained by slow evaporation of a methanol solution.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus (Bruker, 2003); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I) with displacement ellipsoids for the non-hydrogen atoms drawn at the 50% probability level.
	Fig. 2. The packing of (I), viewed down the b axis. The dashed lines represent the hydrogen bonding interactions.

(I) top

Crystal data top

C₁₇H₁₇ClN₂O₄·CH₄O	F(000) = 800
M_r = 380.82	D_x = 1.365 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 5318 reflections
a = 12.9356 (7) Å	θ = 2.6–27.0°
b = 4.8718 (3) Å	µ = 0.24 mm⁻¹
c = 29.4119 (16) Å	T = 173 K
V = 1853.53 (18) Å³	Block, colorless
Z = 4	0.48 × 0.40 × 0.39 mm

Data collection top

Bruker SMART 1000 CCD diffractometer	3916 independent reflections
Radiation source: fine-focus sealed tube	3561 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ω scans	θ_max = 27.0°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −16→8
T_min = 0.895, T_max = 0.913	k = −5→6
9008 measured reflections	l = −37→36

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.031	H-atom parameters constrained
wR(F²) = 0.080	w = 1/[σ²(F_o²) + (0.039P)² + 0.3064P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max = 0.012
3916 reflections	Δρ_max = 0.20 e Å⁻³
240 parameters	Δρ_min = −0.17 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1846 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.04 (5)

Crystal data top

C₁₇H₁₇ClN₂O₄·CH₄O	V = 1853.53 (18) Å³
M_r = 380.82	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 12.9356 (7) Å	µ = 0.24 mm⁻¹
b = 4.8718 (3) Å	T = 173 K
c = 29.4119 (16) Å	0.48 × 0.40 × 0.39 mm

Data collection top

Bruker SMART 1000 CCD diffractometer	3916 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	3561 reflections with I > 2σ(I)
T_min = 0.895, T_max = 0.913	R_int = 0.021
9008 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	H-atom parameters constrained
wR(F²) = 0.080	Δρ_max = 0.20 e Å⁻³
S = 1.09	Δρ_min = −0.17 e Å⁻³
3916 reflections	Absolute structure: Flack (1983), 1846 Friedel pairs
240 parameters	Absolute structure parameter: 0.04 (5)
1 restraint

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
Cl1	0.88399 (4)	−0.29291 (12)	0.98890 (2)	0.04522 (15)
C1	0.93423 (13)	0.2105 (4)	0.75620 (6)	0.0215 (3)
C2	0.85309 (13)	0.0229 (4)	0.75340 (6)	0.0211 (3)
H2	0.8352	−0.0866	0.7789	0.025*
C3	0.79858 (12)	−0.0025 (3)	0.71285 (6)	0.0213 (3)
C4	0.82468 (13)	0.1595 (3)	0.67522 (6)	0.0209 (3)
C5	0.90935 (13)	0.3386 (4)	0.67796 (6)	0.0221 (3)
C6	0.96347 (13)	0.3656 (4)	0.71860 (6)	0.0216 (3)
H6	1.0201	0.4892	0.7207	0.026*
C7	0.99585 (13)	0.2484 (4)	0.79886 (6)	0.0231 (4)
C8	0.96354 (14)	0.0864 (4)	0.91319 (7)	0.0308 (4)
H8	0.8949	0.0174	0.9121	0.037*
C9	1.02227 (15)	0.0827 (4)	0.95597 (6)	0.0286 (4)
C10	0.99287 (15)	−0.0824 (4)	0.99280 (7)	0.0319 (4)
C11	1.04956 (19)	−0.0869 (5)	1.03275 (7)	0.0403 (5)
H11	1.0289	−0.2029	1.0571	0.048*
C12	1.13525 (18)	0.0753 (5)	1.03723 (7)	0.0435 (5)
H12	1.1731	0.0753	1.0649	0.052*
C13	1.16701 (18)	0.2405 (5)	1.00118 (7)	0.0416 (5)
H13	1.2270	0.3517	1.0041	0.050*
C14	1.11093 (16)	0.2419 (5)	0.96120 (7)	0.0362 (5)
H14	1.1334	0.3541	0.9367	0.043*
C15	0.69115 (15)	−0.3585 (4)	0.74240 (6)	0.0260 (4)
H15A	0.7517	−0.4661	0.7515	0.039*
H15B	0.6361	−0.4827	0.7324	0.039*
H15C	0.6668	−0.2497	0.7683	0.039*
C16	0.71561 (18)	0.3559 (4)	0.61922 (7)	0.0386 (5)
H16A	0.6581	0.3954	0.6399	0.058*
H16B	0.6884	0.3175	0.5888	0.058*
H16C	0.7619	0.5150	0.6179	0.058*
C17	1.01472 (14)	0.6703 (4)	0.63995 (7)	0.0302 (4)
H17A	0.9989	0.8111	0.6627	0.045*
H17B	1.0217	0.7565	0.6100	0.045*
H17C	1.0796	0.5785	0.6480	0.045*
C18	1.2215 (2)	0.7735 (5)	0.86998 (9)	0.0501 (6)
H18A	1.1903	0.7780	0.9003	0.075*
H18B	1.1739	0.8569	0.8480	0.075*
H18C	1.2866	0.8763	0.8703	0.075*
N1	0.94896 (12)	0.1728 (3)	0.83814 (5)	0.0268 (3)
H1	0.8841	0.1185	0.8385	0.032*
N2	1.00645 (11)	0.1840 (3)	0.87756 (5)	0.0269 (3)
O1	0.71872 (9)	−0.1791 (3)	0.70587 (4)	0.0259 (3)
O2	0.77131 (9)	0.1235 (3)	0.63530 (4)	0.0259 (3)
O3	0.93290 (10)	0.4729 (3)	0.63872 (4)	0.0308 (3)
O4	1.08391 (10)	0.3399 (3)	0.79778 (4)	0.0298 (3)
O5	1.24118 (9)	0.4964 (3)	0.85732 (5)	0.0328 (3)
H5	1.1900	0.4338	0.8431	0.049*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0469 (3)	0.0485 (3)	0.0403 (3)	−0.0043 (2)	0.0087 (2)	0.0094 (3)
C1	0.0212 (8)	0.0249 (9)	0.0183 (8)	0.0027 (7)	−0.0023 (7)	−0.0007 (7)
C2	0.0216 (8)	0.0220 (8)	0.0196 (8)	0.0027 (6)	0.0005 (7)	0.0018 (7)
C3	0.0197 (8)	0.0211 (8)	0.0231 (8)	0.0018 (6)	0.0002 (7)	−0.0038 (7)
C4	0.0212 (8)	0.0242 (9)	0.0171 (8)	0.0044 (7)	−0.0033 (6)	−0.0027 (6)
C5	0.0219 (8)	0.0239 (9)	0.0205 (8)	0.0015 (7)	0.0007 (6)	0.0009 (7)
C6	0.0205 (8)	0.0243 (8)	0.0201 (8)	−0.0005 (7)	−0.0017 (6)	−0.0003 (7)
C7	0.0219 (8)	0.0280 (9)	0.0195 (8)	0.0017 (7)	−0.0028 (7)	−0.0007 (7)
C8	0.0255 (9)	0.0425 (11)	0.0244 (9)	−0.0010 (8)	−0.0022 (7)	0.0010 (8)
C9	0.0308 (10)	0.0370 (10)	0.0179 (8)	0.0040 (8)	−0.0003 (7)	−0.0002 (8)
C10	0.0353 (10)	0.0339 (10)	0.0266 (9)	0.0074 (8)	0.0055 (8)	−0.0001 (8)
C11	0.0580 (14)	0.0406 (12)	0.0221 (9)	0.0135 (11)	0.0047 (9)	0.0069 (9)
C12	0.0540 (14)	0.0538 (14)	0.0227 (9)	0.0139 (11)	−0.0115 (9)	−0.0045 (10)
C13	0.0419 (12)	0.0519 (14)	0.0309 (11)	0.0028 (10)	−0.0109 (9)	−0.0042 (10)
C14	0.0397 (11)	0.0458 (12)	0.0233 (9)	−0.0009 (10)	−0.0031 (8)	0.0043 (9)
C15	0.0269 (9)	0.0232 (9)	0.0278 (9)	−0.0019 (7)	0.0025 (7)	−0.0004 (7)
C16	0.0433 (12)	0.0374 (11)	0.0351 (11)	0.0081 (10)	−0.0179 (9)	−0.0010 (9)
C17	0.0269 (9)	0.0345 (10)	0.0293 (9)	−0.0029 (8)	−0.0006 (8)	0.0078 (8)
C18	0.0638 (15)	0.0453 (13)	0.0412 (13)	0.0120 (12)	−0.0099 (12)	−0.0078 (11)
N1	0.0206 (7)	0.0415 (9)	0.0184 (7)	−0.0044 (6)	−0.0041 (6)	0.0019 (6)
N2	0.0257 (7)	0.0370 (9)	0.0180 (7)	0.0010 (6)	−0.0053 (6)	0.0009 (6)
O1	0.0263 (6)	0.0282 (7)	0.0232 (6)	−0.0049 (5)	−0.0047 (5)	0.0008 (5)
O2	0.0292 (6)	0.0276 (6)	0.0208 (6)	0.0011 (5)	−0.0064 (5)	−0.0028 (5)
O3	0.0309 (6)	0.0399 (7)	0.0217 (6)	−0.0096 (6)	−0.0052 (6)	0.0076 (6)
O4	0.0243 (6)	0.0426 (8)	0.0225 (7)	−0.0089 (6)	−0.0040 (5)	0.0029 (6)
O5	0.0231 (6)	0.0405 (7)	0.0347 (7)	0.0025 (6)	−0.0042 (5)	−0.0078 (6)

Geometric parameters (Å, º) top

Cl1—C10	1.746 (2)	C12—H12	0.9500
C1—C6	1.392 (2)	C13—C14	1.382 (3)
C1—C2	1.394 (2)	C13—H13	0.9500
C1—C7	1.498 (2)	C14—H14	0.9500
C2—C3	1.391 (2)	C15—O1	1.430 (2)
C2—H2	0.9500	C15—H15A	0.9800
C3—O1	1.360 (2)	C15—H15B	0.9800
C3—C4	1.401 (2)	C15—H15C	0.9800
C4—O2	1.373 (2)	C16—O2	1.423 (2)
C4—C5	1.402 (2)	C16—H16A	0.9800
C5—O3	1.361 (2)	C16—H16B	0.9800
C5—C6	1.391 (2)	C16—H16C	0.9800
C6—H6	0.9500	C17—O3	1.430 (2)
C7—O4	1.224 (2)	C17—H17A	0.9800
C7—N1	1.356 (2)	C17—H17B	0.9800
C8—N2	1.278 (2)	C17—H17C	0.9800
C8—C9	1.470 (2)	C18—O5	1.423 (3)
C8—H8	0.9500	C18—H18A	0.9800
C9—C14	1.393 (3)	C18—H18B	0.9800
C9—C10	1.402 (3)	C18—H18C	0.9800
C10—C11	1.385 (3)	N1—N2	1.378 (2)
C11—C12	1.368 (3)	N1—H1	0.8800
C11—H11	0.9500	O5—H5	0.8400
C12—C13	1.393 (3)

C6—C1—C2	120.90 (15)	C14—C13—H13	120.1
C6—C1—C7	117.00 (15)	C12—C13—H13	120.1
C2—C1—C7	122.07 (14)	C13—C14—C9	121.6 (2)
C3—C2—C1	119.38 (15)	C13—C14—H14	119.2
C3—C2—H2	120.3	C9—C14—H14	119.2
C1—C2—H2	120.3	O1—C15—H15A	109.5
O1—C3—C2	124.80 (15)	O1—C15—H15B	109.5
O1—C3—C4	114.85 (15)	H15A—C15—H15B	109.5
C2—C3—C4	120.34 (15)	O1—C15—H15C	109.5
O2—C4—C3	118.83 (15)	H15A—C15—H15C	109.5
O2—C4—C5	121.43 (15)	H15B—C15—H15C	109.5
C3—C4—C5	119.55 (14)	O2—C16—H16A	109.5
O3—C5—C6	124.76 (15)	O2—C16—H16B	109.5
O3—C5—C4	115.15 (14)	H16A—C16—H16B	109.5
C6—C5—C4	120.09 (15)	O2—C16—H16C	109.5
C5—C6—C1	119.63 (16)	H16A—C16—H16C	109.5
C5—C6—H6	120.2	H16B—C16—H16C	109.5
C1—C6—H6	120.2	O3—C17—H17A	109.5
O4—C7—N1	122.52 (16)	O3—C17—H17B	109.5
O4—C7—C1	121.23 (15)	H17A—C17—H17B	109.5
N1—C7—C1	116.24 (15)	O3—C17—H17C	109.5
N2—C8—C9	118.82 (17)	H17A—C17—H17C	109.5
N2—C8—H8	120.6	H17B—C17—H17C	109.5
C9—C8—H8	120.6	O5—C18—H18A	109.5
C14—C9—C10	117.21 (17)	O5—C18—H18B	109.5
C14—C9—C8	120.89 (18)	H18A—C18—H18B	109.5
C10—C9—C8	121.89 (18)	O5—C18—H18C	109.5
C11—C10—C9	121.40 (19)	H18A—C18—H18C	109.5
C11—C10—Cl1	118.27 (16)	H18B—C18—H18C	109.5
C9—C10—Cl1	120.33 (15)	C7—N1—N2	117.68 (14)
C12—C11—C10	120.1 (2)	C7—N1—H1	121.2
C12—C11—H11	119.9	N2—N1—H1	121.2
C10—C11—H11	119.9	C8—N2—N1	116.16 (15)
C11—C12—C13	119.97 (19)	C3—O1—C15	117.56 (13)
C11—C12—H12	120.0	C4—O2—C16	115.90 (14)
C13—C12—H12	120.0	C5—O3—C17	117.86 (14)
C14—C13—C12	119.7 (2)	C18—O5—H5	109.5

C6—C1—C2—C3	−2.2 (2)	C14—C9—C10—C11	0.1 (3)
C7—C1—C2—C3	179.86 (15)	C8—C9—C10—C11	179.16 (19)
C1—C2—C3—O1	179.51 (15)	C14—C9—C10—Cl1	−178.94 (15)
C1—C2—C3—C4	−0.2 (2)	C8—C9—C10—Cl1	0.2 (3)
O1—C3—C4—O2	−1.7 (2)	C9—C10—C11—C12	1.1 (3)
C2—C3—C4—O2	178.07 (15)	Cl1—C10—C11—C12	−179.86 (17)
O1—C3—C4—C5	−176.74 (15)	C10—C11—C12—C13	−1.5 (3)
C2—C3—C4—C5	3.0 (2)	C11—C12—C13—C14	0.7 (3)
O2—C4—C5—O3	0.7 (2)	C12—C13—C14—C9	0.5 (3)
C3—C4—C5—O3	175.62 (15)	C10—C9—C14—C13	−0.8 (3)
O2—C4—C5—C6	−178.40 (16)	C8—C9—C14—C13	−180.0 (2)
C3—C4—C5—C6	−3.5 (2)	O4—C7—N1—N2	−4.4 (3)
O3—C5—C6—C1	−177.87 (16)	C1—C7—N1—N2	174.82 (16)
C4—C5—C6—C1	1.1 (3)	C9—C8—N2—N1	177.74 (17)
C2—C1—C6—C5	1.7 (3)	C7—N1—N2—C8	−173.39 (17)
C7—C1—C6—C5	179.79 (15)	C2—C3—O1—C15	−2.3 (2)
C6—C1—C7—O4	−21.9 (3)	C4—C3—O1—C15	177.43 (14)
C2—C1—C7—O4	156.15 (17)	C3—C4—O2—C16	118.71 (19)
C6—C1—C7—N1	158.87 (16)	C5—C4—O2—C16	−66.3 (2)
C2—C1—C7—N1	−23.1 (2)	C6—C5—O3—C17	−4.5 (3)
N2—C8—C9—C14	16.3 (3)	C4—C5—O3—C17	176.48 (15)
N2—C8—C9—C10	−162.78 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O5ⁱ	0.88	2.01	2.8673 (19)	165
O5—H5···O4	0.84	1.97	2.7904 (18)	166

Symmetry code: (i) x−1/2, −y+1/2, z.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₇ClN₂O₄·CH₄O
M_r	380.82
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	173
a, b, c (Å)	12.9356 (7), 4.8718 (3), 29.4119 (16)
V (Å³)	1853.53 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.48 × 0.40 × 0.39

Data collection
Diffractometer	Bruker SMART 1000 CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.895, 0.913
No. of measured, independent and observed [I > 2σ(I)] reflections	9008, 3916, 3561
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.080, 1.09
No. of reflections	3916
No. of parameters	240
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.17
Absolute structure	Flack (1983), 1846 Friedel pairs
Absolute structure parameter	0.04 (5)

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2003), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O5ⁱ	0.88	2.01	2.8673 (19)	165
O5—H5···O4	0.84	1.97	2.7904 (18)	166

Symmetry code: (i) x−1/2, −y+1/2, z.

Acknowledgements

The authors thank the Natural Science Youth Foundation of South China University of Technology for financial assistance (E5050570).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin. Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bernardino, A. M. R., Gomes, A. O., Charret, K. S., Freita, A. C. C., Machado, G. M. C., Canto-Cavalheiro, M. M., Leon, L. L. & Amaral, V. F. (2006). Eur. J. Med. Chem. 41, 80–87. Web of Science CrossRef PubMed CAS Google Scholar
Bruker (2001). SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2003). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Ganjali, M. R., Faridbod, F., Norouzi, P. & Adib, M. (2006). Sens. Actuators B, 120, 119–124. Web of Science CrossRef CAS Google Scholar
Gardner, T. S., Weins, R. & Lee, J. (1991). J. Org. Chem. 26, 1514–1530. CrossRef Web of Science Google Scholar
Patole, J., Sandbhor, U., Padhye, S., Deobagkar, D. N., Anson, C. E. & Powell, A. (2003). Bioorg. Med. Chem. Lett. 13, 51–55. Web of Science CSD CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2003). 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