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

Zhu, Y.-C.; He, D.-H.

doi:10.1107/S1600536808021764

organic compounds

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Volume 64| Part 8| August 2008| Page o1630

doi:10.1107/S1600536808021764

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

Yong-Chuang Zhu ^a and Dao-Hang He ^a ^*

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

(Received 8 July 2008; accepted 13 July 2008; online 31 July 2008)

The title compound, C₁₇H₁₇BrN₂O₄·CH₄O, was synthesized by the condensation of 3,4,5-trimethoxybenzohydrazide and 2-bromobenzaldehyde. The two aromatic rings are approximately planar, the dihedral angle being 3.08 (9)°. The molecules are linked by intermolecular N—H⋯O and O—H⋯O hydrogen bonds into chains along the a axis.

Related literature

For related literature, see: Constable & Holmes (1987 ); Ganjali et al. (2006 ); Gardner et al. (1991 ); Jing et al. (2006 ); Kuriakose et al. (2007 ); Patole et al. (2003 ); Zhou et al. (2005 ).

Experimental

Crystal data

C₁₇H₁₇BrN₂O₄·CH₄O
M_r = 425.28
Orthorhombic, P n a 2₁
a = 12.9234 (7) Å
b = 4.9159 (3) Å
c = 29.3975 (17) Å
V = 1867.63 (19) Å³
Z = 4
Mo Kα radiation
μ = 2.23 mm⁻¹
T = 173 (2) K
0.36 × 0.35 × 0.33 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.455, T_max = 0.479
8158 measured reflections
3799 independent reflections
3206 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.080
S = 1.04
3799 reflections
240 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.26 e Å⁻³
Absolute structure: Flack (1983 ), 1720 Friedel pairs
Flack parameter: −0.008 (8)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O5ⁱ	0.88	2.01	2.871 (4)	164
O5—H5⋯O4	0.84	1.96	2.794 (3)	175
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z]$ .

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, global. DOI: 10.1107/S1600536808021764/wn2271sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808021764/wn2271Isup2.hkl

checkCIF report

Comment top

Hydrazones are acknowledged to possess a diverse range of bioactivities; these include antibacterial, antiviral, antineoplastic, and anti-inflammatory (Constable & Holmes, 1987; Ganjali et al., 2006; Gardner et al., 1991; Patole et al., 2003). In addition, many hydrazones have also been used as ligands because they can readily form stable complexes with most metal ions (Kuriakose et al., 2007; Zhou et al., 2005). We report here the synthesis and crystal structure of the title compound, obtained by the condensation of 3,4,5-trimethoxybenzohydrazide and 2-bromobenzaldehyde.

The asymmetric unit of the title compound comprises one N'-(2-bromobenzylidene)-3,4,5-trimethoxybenzohydrazide and a methanol solvent molecule (Fig. 1). The two aromatic rings are approximately planar, with a dihedral angle of 3.08 (9)°. Similar geometry has been observed in related hydrazone analogues (Jing et al., 2006). The methanol molecules in the crystal structure are linked to N'-(2-bromobenzylidene)-3,4,5-trimethoxybenzohydrazide through intermolecular N—H···O and O—H···O hydrogen bonds into chains along the a axis (Fig. 2).

Related literature top

For related literature, see: Constable & Holmes (1987); Ganjali et al. (2006); Gardner et al. (1991); Jing et al. (2006); Kuriakose et al. (2007); Patole et al. (2003); Zhou et al. (2005).

Experimental top

A mixture of 3,4,5-trimethoxybenzohydrazide (1 mmol) and 2-bromobenzaldehyde (1 mmol) 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 single crystals suitable for X-ray analysis 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 structure of the two independent molecules in the asymmetric unit of the title compound, with the atom numbering. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms are represented by spheres of arbitrary radius.
	Fig. 2. The packing of the title compound, viewed down the b axis. The dashed lines represent the hydrogen bonds. H atoms not involved in hydrogen bonding have been omitted.

N'-(2-Bromobenzylidene)-3,4,5-trimethoxybenzohydrazide methanol solvate top

Crystal data top

C₁₇H₁₇BrN₂O₄·CH₄O	F(000) = 872
M_r = 425.28	D_x = 1.512 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 4139 reflections
a = 12.9234 (7) Å	θ = 2.8–26.8°
b = 4.9159 (3) Å	µ = 2.23 mm⁻¹
c = 29.3975 (17) Å	T = 173 K
V = 1867.63 (19) Å³	Block, colorless
Z = 4	0.36 × 0.35 × 0.33 mm

Data collection top

Bruker SMART 1000 CCD diffractometer	3799 independent reflections
Radiation source: fine-focus sealed tube	3206 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω scans	θ_max = 27.0°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −15→16
T_min = 0.455, T_max = 0.479	k = −2→6
8158 measured reflections	l = −34→37

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)] = 0.030	H-atom parameters constrained
wR(F²) = 0.080	w = 1/[σ²(F_o²) + 0.8008P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
3799 reflections	Δρ_max = 0.33 e Å⁻³
240 parameters	Δρ_min = −0.26 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1720 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.008 (8)

Crystal data top

C₁₇H₁₇BrN₂O₄·CH₄O	V = 1867.63 (19) Å³
M_r = 425.28	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 12.9234 (7) Å	µ = 2.23 mm⁻¹
b = 4.9159 (3) Å	T = 173 K
c = 29.3975 (17) Å	0.36 × 0.35 × 0.33 mm

Data collection top

Bruker SMART 1000 CCD diffractometer	3799 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	3206 reflections with I > 2σ(I)
T_min = 0.455, T_max = 0.479	R_int = 0.027
8158 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	H-atom parameters constrained
wR(F²) = 0.080	Δρ_max = 0.33 e Å⁻³
S = 1.04	Δρ_min = −0.26 e Å⁻³
3799 reflections	Absolute structure: Flack (1983), 1720 Friedel pairs
240 parameters	Absolute structure parameter: −0.008 (8)
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
Br1	0.61656 (2)	1.31840 (7)	0.659414 (16)	0.03707 (11)
C1	0.5590 (2)	0.7908 (6)	0.89278 (10)	0.0193 (6)
C2	0.6409 (2)	0.9755 (6)	0.89566 (11)	0.0195 (6)
H2	0.6593	1.0831	0.8701	0.023*
C3	0.6953 (2)	1.0008 (6)	0.93627 (11)	0.0207 (7)
C4	0.6698 (2)	0.8389 (6)	0.97327 (10)	0.0186 (6)
C5	0.5855 (2)	0.6608 (6)	0.97056 (11)	0.0215 (7)
C6	0.5308 (2)	0.6357 (6)	0.93023 (11)	0.0211 (7)
H6	0.4742	0.5129	0.9282	0.025*
C7	0.4968 (2)	0.7557 (6)	0.85047 (11)	0.0212 (7)
C8	0.5282 (3)	0.9221 (7)	0.73624 (12)	0.0276 (7)
H8	0.5962	0.9952	0.7377	0.033*
C9	0.4707 (3)	0.9235 (7)	0.69320 (11)	0.0254 (7)
C10	0.4991 (2)	1.0835 (6)	0.65573 (14)	0.0264 (7)
C11	0.4448 (3)	1.0814 (8)	0.61551 (12)	0.0337 (8)
H11	0.4657	1.1955	0.5911	0.040*
C12	0.3603 (3)	0.9139 (8)	0.61066 (13)	0.0362 (9)
H12	0.3235	0.9084	0.5827	0.043*
C13	0.3292 (3)	0.7520 (8)	0.64720 (12)	0.0344 (9)
H13	0.2709	0.6357	0.6441	0.041*
C14	0.3830 (3)	0.7604 (8)	0.68790 (14)	0.0312 (8)
H14	0.3598	0.6530	0.7127	0.037*
C15	0.8028 (3)	1.3547 (7)	0.90665 (12)	0.0254 (7)
H15A	0.8276	1.2478	0.8807	0.038*
H15B	0.8577	1.4779	0.9168	0.038*
H15C	0.7422	1.4611	0.8975	0.038*
C16	0.7819 (3)	0.6441 (7)	1.02794 (14)	0.0378 (9)
H16A	0.7402	0.4792	1.0242	0.057*
H16B	0.8003	0.6660	1.0601	0.057*
H16C	0.8451	0.6289	1.0097	0.057*
C17	0.4812 (3)	0.3298 (7)	1.00811 (13)	0.0294 (8)
H17A	0.4160	0.4211	1.0006	0.044*
H17B	0.4748	0.2407	1.0378	0.044*
H17C	0.4968	0.1932	0.9848	0.044*
C18	0.2740 (4)	0.2319 (9)	0.78016 (15)	0.0461 (11)
H18A	0.3183	0.2281	0.7531	0.069*
H18B	0.2092	0.1360	0.7737	0.069*
H18C	0.3096	0.1426	0.8055	0.069*
N2	0.4860 (2)	0.8218 (6)	0.77170 (9)	0.0247 (6)
N1	0.5432 (2)	0.8335 (6)	0.81116 (9)	0.0254 (6)
H1A	0.6079	0.8897	0.8109	0.030*
O1	0.77516 (17)	1.1759 (4)	0.94291 (7)	0.0240 (5)
O2	0.72395 (17)	0.8738 (5)	1.01327 (8)	0.0247 (5)
O3	0.56273 (16)	0.5255 (5)	1.00977 (8)	0.0279 (5)
O4	0.40936 (17)	0.6632 (5)	0.85149 (8)	0.0282 (5)
O5	0.25214 (18)	0.5045 (5)	0.79189 (9)	0.0319 (6)
H5	0.2973	0.5615	0.8101	0.048*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.03845 (18)	0.03817 (18)	0.03459 (19)	−0.00184 (16)	0.0079 (2)	0.0056 (2)
C1	0.0208 (15)	0.0234 (15)	0.0137 (16)	0.0046 (13)	−0.0037 (12)	−0.0005 (12)
C2	0.0212 (15)	0.0209 (15)	0.0165 (16)	0.0034 (13)	−0.0004 (12)	0.0008 (12)
C3	0.0181 (14)	0.0212 (16)	0.0228 (17)	0.0016 (13)	0.0009 (13)	−0.0054 (13)
C4	0.0209 (15)	0.0203 (15)	0.0144 (16)	0.0027 (13)	−0.0023 (12)	−0.0036 (12)
C5	0.0218 (15)	0.0231 (17)	0.0195 (17)	0.0003 (13)	−0.0024 (13)	0.0030 (13)
C6	0.0201 (15)	0.0238 (16)	0.0194 (17)	0.0007 (13)	−0.0051 (12)	0.0003 (13)
C7	0.0206 (15)	0.0247 (16)	0.0183 (16)	0.0010 (13)	−0.0012 (13)	−0.0004 (12)
C8	0.0235 (16)	0.0360 (18)	0.0232 (18)	−0.0025 (15)	−0.0004 (14)	0.0030 (15)
C9	0.0271 (17)	0.0318 (17)	0.0172 (17)	0.0048 (15)	−0.0029 (13)	−0.0024 (13)
C10	0.0313 (15)	0.0282 (14)	0.0196 (17)	0.0088 (12)	0.0059 (18)	−0.0007 (16)
C11	0.047 (2)	0.037 (2)	0.0170 (18)	0.0092 (18)	0.0041 (16)	0.0035 (15)
C12	0.047 (2)	0.043 (2)	0.0192 (19)	0.0102 (19)	−0.0100 (16)	−0.0003 (16)
C13	0.0344 (18)	0.042 (2)	0.027 (2)	−0.0003 (16)	−0.0079 (16)	−0.0059 (14)
C14	0.033 (2)	0.040 (2)	0.021 (2)	0.0007 (18)	−0.0008 (15)	0.0053 (14)
C15	0.0242 (16)	0.0260 (18)	0.0260 (19)	−0.0014 (15)	0.0021 (14)	−0.0016 (14)
C16	0.040 (2)	0.036 (2)	0.037 (2)	0.0072 (19)	−0.0187 (18)	−0.0032 (17)
C17	0.0250 (17)	0.0339 (19)	0.0294 (19)	−0.0035 (16)	0.0007 (14)	0.0083 (16)
C18	0.057 (3)	0.046 (2)	0.036 (2)	0.011 (2)	−0.004 (2)	−0.0082 (19)
N2	0.0217 (13)	0.0366 (16)	0.0159 (14)	−0.0002 (12)	−0.0058 (11)	0.0011 (12)
N1	0.0185 (13)	0.0413 (18)	0.0162 (14)	−0.0031 (13)	−0.0030 (10)	0.0024 (12)
O1	0.0251 (11)	0.0277 (12)	0.0193 (12)	−0.0046 (10)	−0.0042 (9)	0.0012 (9)
O2	0.0305 (12)	0.0285 (12)	0.0150 (12)	−0.0001 (10)	−0.0068 (10)	−0.0019 (9)
O3	0.0277 (12)	0.0379 (13)	0.0181 (12)	−0.0087 (11)	−0.0042 (10)	0.0067 (10)
O4	0.0232 (11)	0.0409 (14)	0.0205 (13)	−0.0073 (11)	−0.0049 (10)	0.0038 (10)
O5	0.0230 (12)	0.0402 (14)	0.0326 (14)	0.0039 (11)	−0.0045 (11)	−0.0067 (11)

Geometric parameters (Å, º) top

Br1—C10	1.911 (3)	C12—H12	0.9500
C1—C6	1.388 (4)	C13—C14	1.384 (5)
C1—C2	1.397 (4)	C13—H13	0.9500
C1—C7	1.491 (4)	C14—H14	0.9500
C2—C3	1.391 (4)	C15—O1	1.427 (4)
C2—H2	0.9500	C15—H15A	0.9800
C3—O1	1.358 (4)	C15—H15B	0.9800
C3—C4	1.388 (4)	C15—H15C	0.9800
C4—O2	1.379 (4)	C16—O2	1.422 (4)
C4—C5	1.400 (5)	C16—H16A	0.9800
C5—O3	1.363 (4)	C16—H16B	0.9800
C5—C6	1.386 (4)	C16—H16C	0.9800
C6—H6	0.9500	C17—O3	1.428 (4)
C7—O4	1.218 (4)	C17—H17A	0.9800
C7—N1	1.357 (4)	C17—H17B	0.9800
C8—N2	1.276 (4)	C17—H17C	0.9800
C8—C9	1.467 (4)	C18—O5	1.412 (5)
C8—H8	0.9500	C18—H18A	0.9800
C9—C14	1.398 (5)	C18—H18B	0.9800
C9—C10	1.402 (5)	C18—H18C	0.9800
C10—C11	1.375 (5)	N2—N1	1.377 (4)
C11—C12	1.375 (6)	N1—H1A	0.8800
C11—H11	0.9500	O5—H5	0.8400
C12—C13	1.396 (5)

C6—C1—C2	120.5 (3)	C14—C13—H13	119.9
C6—C1—C7	117.1 (3)	C12—C13—H13	119.9
C2—C1—C7	122.3 (3)	C13—C14—C9	121.4 (4)
C3—C2—C1	119.5 (3)	C13—C14—H14	119.3
C3—C2—H2	120.2	C9—C14—H14	119.3
C1—C2—H2	120.2	O1—C15—H15A	109.5
O1—C3—C4	115.6 (3)	O1—C15—H15B	109.5
O1—C3—C2	124.3 (3)	H15A—C15—H15B	109.5
C4—C3—C2	120.1 (3)	O1—C15—H15C	109.5
O2—C4—C3	118.5 (3)	H15A—C15—H15C	109.5
O2—C4—C5	121.4 (3)	H15B—C15—H15C	109.5
C3—C4—C5	119.9 (3)	O2—C16—H16A	109.5
O3—C5—C6	124.7 (3)	O2—C16—H16B	109.5
O3—C5—C4	115.2 (3)	H16A—C16—H16B	109.5
C6—C5—C4	120.1 (3)	O2—C16—H16C	109.5
C5—C6—C1	119.7 (3)	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	122.4 (3)	O3—C17—H17B	109.5
O4—C7—C1	121.5 (3)	H17A—C17—H17B	109.5
N1—C7—C1	116.1 (3)	O3—C17—H17C	109.5
N2—C8—C9	119.3 (3)	H17A—C17—H17C	109.5
N2—C8—H8	120.3	H17B—C17—H17C	109.5
C9—C8—H8	120.3	O5—C18—H18A	109.5
C14—C9—C10	116.5 (3)	O5—C18—H18B	109.5
C14—C9—C8	120.3 (3)	H18A—C18—H18B	109.5
C10—C9—C8	123.2 (3)	O5—C18—H18C	109.5
C11—C10—C9	122.6 (3)	H18A—C18—H18C	109.5
C11—C10—Br1	117.3 (3)	H18B—C18—H18C	109.5
C9—C10—Br1	120.1 (3)	C8—N2—N1	116.2 (3)
C12—C11—C10	119.9 (3)	C7—N1—N2	117.9 (3)
C12—C11—H11	120.0	C7—N1—H1A	121.1
C10—C11—H11	120.0	N2—N1—H1A	121.1
C11—C12—C13	119.4 (3)	C3—O1—C15	118.2 (2)
C11—C12—H12	120.3	C4—O2—C16	115.3 (2)
C13—C12—H12	120.3	C5—O3—C17	117.4 (3)
C14—C13—C12	120.2 (4)	C18—O5—H5	109.5

C6—C1—C2—C3	0.9 (4)	C14—C9—C10—C11	−0.5 (5)
C7—C1—C2—C3	179.4 (3)	C8—C9—C10—C11	179.6 (3)
C1—C2—C3—O1	−179.2 (3)	C14—C9—C10—Br1	179.1 (2)
C1—C2—C3—C4	1.5 (4)	C8—C9—C10—Br1	−0.9 (4)
O1—C3—C4—O2	2.0 (4)	C9—C10—C11—C12	−1.2 (5)
C2—C3—C4—O2	−178.6 (3)	Br1—C10—C11—C12	179.2 (3)
O1—C3—C4—C5	177.0 (3)	C10—C11—C12—C13	1.5 (5)
C2—C3—C4—C5	−3.6 (4)	C11—C12—C13—C14	0.0 (6)
O2—C4—C5—O3	−0.7 (4)	C12—C13—C14—C9	−1.8 (6)
C3—C4—C5—O3	−175.6 (3)	C10—C9—C14—C13	1.9 (5)
O2—C4—C5—C6	178.2 (3)	C8—C9—C14—C13	−178.1 (3)
C3—C4—C5—C6	3.3 (4)	C9—C8—N2—N1	−178.4 (3)
O3—C5—C6—C1	177.8 (3)	O4—C7—N1—N2	4.1 (5)
C4—C5—C6—C1	−1.0 (5)	C1—C7—N1—N2	−175.7 (3)
C2—C1—C6—C5	−1.2 (5)	C8—N2—N1—C7	173.1 (3)
C7—C1—C6—C5	−179.7 (3)	C4—C3—O1—C15	−177.9 (3)
C6—C1—C7—O4	21.3 (4)	C2—C3—O1—C15	2.7 (4)
C2—C1—C7—O4	−157.2 (3)	C3—C4—O2—C16	−117.3 (3)
C6—C1—C7—N1	−159.0 (3)	C5—C4—O2—C16	67.8 (4)
C2—C1—C7—N1	22.5 (4)	C6—C5—O3—C17	4.7 (5)
N2—C8—C9—C14	−15.7 (5)	C4—C5—O3—C17	−176.5 (3)
N2—C8—C9—C10	164.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O5ⁱ	0.88	2.01	2.871 (4)	164
O5—H5···O4	0.84	1.96	2.794 (3)	175

Symmetry code: (i) x+1/2, −y+3/2, z.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₇BrN₂O₄·CH₄O
M_r	425.28
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	173
a, b, c (Å)	12.9234 (7), 4.9159 (3), 29.3975 (17)
V (Å³)	1867.63 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.23
Crystal size (mm)	0.36 × 0.35 × 0.33

Data collection
Diffractometer	Bruker SMART 1000 CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.455, 0.479
No. of measured, independent and observed [I > 2σ(I)] reflections	8158, 3799, 3206
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.080, 1.04
No. of reflections	3799
No. of parameters	240
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.26
Absolute structure	Flack (1983), 1720 Friedel pairs
Absolute structure parameter	−0.008 (8)

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—H1A···O5ⁱ	0.88	2.01	2.871 (4)	164.2
O5—H5···O4	0.84	1.96	2.794 (3)	174.8

Symmetry code: (i) x+1/2, −y+3/2, z.

Acknowledgements

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

References

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