2-Hydr­oxy-N′-(4-isopropyl­cyclo­hexyl­carbon­yl)-3-methyl­benzohydrazide

Shu, T.-P.; Wen, J.-L.; Chen, S.-Z.; Lei, K.-W.

doi:10.1107/S160053680900556X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page o575

doi:10.1107/S160053680900556X

Open

access

ADDENDA AND ERRATA

A correction has been published for this article. To view the correction, click here.

2-Hydroxy-N′-(4-isopropylcyclohexylcarbonyl)-3-methylbenzohydrazide

Tian-Pin Shu,^a Jun-Long Wen,^a Su-Zhen Chen ^a and Ke-Wei Lei ^a ^*

^aState Key Laboratory Base of Novel Functional Materials and Preparation Science, Institute of Solid Materials Chemistry, Faculty of Materials Science and Chemical Engineering, Ningbo University, Ningbo 315211, People's Republic of China
^*Correspondence e-mail: leikeweipublic@hotmail.com

(Received 23 December 2008; accepted 17 February 2009; online 21 February 2009)

The crystal structure of the title compound, C₁₈H₂₆N₂O₃, is stabilized by intermolecular N—H⋯O and O—H⋯O hydrogen bonds. One of the methyl groups is disordered with occupancies of 0.51 (3):0.49 (3).

Related literature

For the properties of metallocrowns, see: Alexiou et al. (2002 ); Gaynor et al. (2002 ); Lah & Pecoraro (1989 ); Lehaire et al. (2002 ); Liu et al. (2001 , 2008 ); Saalfrank et al. (2001 ).

Experimental

Crystal data

C₁₈H₂₆N₂O₃
M_r = 318.41
Monoclinic, P 2₁ /c
a = 16.193 (5) Å
b = 16.194 (5) Å
c = 6.856 (2) Å
β = 97.892 (4)°
V = 1780.8 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.43 × 0.26 × 0.22 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: none T_min = 0.970, T_max = 0.983
8728 measured reflections
6453 independent reflections
3925 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.080
wR(F²) = 0.211
S = 1.05
6453 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.60 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2ⁱ	0.86	2.05	2.821 (4)	149
O1—H1B⋯O3	0.82	1.92	2.636 (4)	145
N2—H2A⋯O3ⁱⁱ	0.86	2.10	2.898 (4)	154
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) -x, -y+1, -z.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680900556X/jh2073sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680900556X/jh2073Isup2.hkl

checkCIF report

Comment top

Metallacrowns are important compounds. Because of their potentially unique properties (Alexiou et al., 2002; Gaynor et al., 2002; Lah & Pecoraro, 1989; Lehaire et al., 2002; Liu et al., 2001; Saalfrank et al., 2001), they have gained increasing attention over the past decade. These compounds can be readily assembled using a trianionic pentadentate ligand,N-acylsalicylhydrazide,having a trivalent octahedral metal ion. The size of the metallacrown can be controlled by modifying the close-contact interaction between the N-acyl residues of the ligands (Liu et al., 2008). We now report structure of a designed pentadentate ligand, N-4-isoPropylcyclohexyl-3-methyl-salicylhydrazide.

A view of the title structure is illustrated in Fig.1. Because of C1 splited into C1 and C1', It made the U_eq of neighbor atoms lower or larger than usual U_eq. The molecular conformation is characterized by N—H···O hydrogen bonds and the crystal packing is stabilized by N—H···O and O—H···O hydrogen bonds(Fig.2).

Related literature top

For the properties of metallocrowns, see: Alexiou et al. (2002); Gaynor et al. (2002); Lah & Pecoraro (1989); Lehaire et al. (2002); Liu et al. (2001, 2008); Saalfrank et al. (2001).

Experimental top

Trimethylaceto chloride (6.025 g, 50.0 mmol) was added to 50 ml chloroform solution of 4-isoPropylcyclohexyl acid with an external ice-water bath and triethylamine(5.200 g, 50.0 mmol). stirred for about 30 min slowly warmed to ambient temperature. To the above solution, 3-methyl-salicylhydrazide (7.636 g, 46.0 mmol)was added and stirred for 30 min. A white suspension began to appear after a while.the resulting white precipitate was filtered and rinsed with chloroform and diethyl ether. The title compound was recrystallized from methanol solution.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The structure of (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme. [symmetry code: (i) –X, 0.5+Y, 0.5-Z].
	Fig. 2. Packing diagram of (I). hydrogen bonds are shown as dashed lines.

2-Hydroxy-N'-(4-isopropylcyclohexylcarbonyl)-3-methylbenzohydrazide top

Crystal data top

C₁₈H₂₆N₂O₃	F(000) = 688
M_r = 318.41	D_x = 1.188 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5099 reflections
a = 16.193 (5) Å	θ = 2.5–26.2°
b = 16.194 (5) Å	µ = 0.08 mm⁻¹
c = 6.856 (2) Å	T = 296 K
β = 97.892 (4)°	Block, colourless
V = 1780.8 (9) Å³	0.43 × 0.26 × 0.22 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	3925 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.025
Graphite monochromator	θ_max = 32.5°, θ_min = 1.8°
ϕ and ω scans	h = −16→24
8728 measured reflections	k = −17→24
6453 independent reflections	l = −7→10

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)] = 0.080	H-atom parameters constrained
wR(F²) = 0.211	w = 1/[σ²(F_o²) + (0.0912P)² + 2.6628P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
6453 reflections	Δρ_max = 0.40 e Å⁻³
217 parameters	Δρ_min = −0.60 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.016 (5)

Crystal data top

C₁₈H₂₆N₂O₃	V = 1780.8 (9) Å³
M_r = 318.41	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.193 (5) Å	µ = 0.08 mm⁻¹
b = 16.194 (5) Å	T = 296 K
c = 6.856 (2) Å	0.43 × 0.26 × 0.22 mm
β = 97.892 (4)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3925 reflections with I > 2σ(I)
8728 measured reflections	R_int = 0.025
6453 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.080	0 restraints
wR(F²) = 0.211	H-atom parameters constrained
S = 1.05	Δρ_max = 0.40 e Å⁻³
6453 reflections	Δρ_min = −0.60 e Å⁻³
217 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	Occ. (<1)
O1	0.26649 (17)	0.4109 (2)	0.1034 (4)	0.0739 (9)
H1B	0.2257	0.4290	0.1481	0.111*
O2	−0.02604 (18)	0.29519 (17)	0.2523 (4)	0.0721 (9)
O3	0.10747 (16)	0.44725 (15)	0.0967 (4)	0.0527 (7)
N1	0.01874 (18)	0.36122 (18)	−0.0854 (5)	0.0512 (9)
H1A	0.0117	0.3227	−0.1724	0.061*
N2	−0.04755 (18)	0.38761 (18)	0.0058 (5)	0.0513 (8)
H2A	−0.0782	0.4274	−0.0462	0.062*
C1	−0.458 (2)	0.3768 (18)	0.388 (6)	0.056 (4)	0.49 (3)
H1C	−0.4868	0.4194	0.3090	0.084*	0.49 (3)
H1D	−0.4921	0.3564	0.4804	0.084*	0.49 (3)
H1E	−0.4444	0.3325	0.3043	0.084*	0.49 (3)
C1'	−0.454 (2)	0.3490 (17)	0.412 (6)	0.056 (4)	0.51 (3)
H1'A	−0.5058	0.3693	0.4471	0.084*	0.51 (3)
H1'B	−0.4431	0.2950	0.4669	0.084*	0.51 (3)
H1'C	−0.4580	0.3460	0.2709	0.084*	0.51 (3)
C2	0.3959 (3)	0.3661 (4)	−0.0978 (10)	0.106 (2)
H2B	0.4317	0.3483	−0.1904	0.159*
H2C	0.4051	0.3319	0.0176	0.159*
H2D	0.4082	0.4225	−0.0618	0.159*
C3	−0.3787 (3)	0.4114 (4)	0.4969 (7)	0.0834 (15)
H3A	−0.3790	0.4699	0.4600	0.100*
C4	−0.2983 (3)	0.3734 (3)	0.2158 (6)	0.0757 (14)
H4A	−0.3073	0.4287	0.1626	0.091*
H4B	−0.3448	0.3394	0.1591	0.091*
C5	−0.3791 (4)	0.4114 (5)	0.7111 (8)	0.119 (2)
H5A	−0.4301	0.4355	0.7407	0.179*
H5B	−0.3326	0.4430	0.7733	0.179*
H5C	−0.3748	0.3556	0.7591	0.179*
C6	−0.2185 (2)	0.3391 (3)	0.1563 (6)	0.0697 (12)
H6A	−0.2224	0.3394	0.0138	0.084*
H6B	−0.2116	0.2824	0.2005	0.084*
C7	0.2006 (3)	0.3240 (3)	−0.4629 (6)	0.0659 (12)
H7A	0.1872	0.3061	−0.5923	0.079*
C8	0.2827 (3)	0.3312 (3)	−0.3797 (7)	0.0722 (13)
H8A	0.3242	0.3168	−0.4546	0.087*
C9	−0.2194 (3)	0.4244 (3)	0.5271 (6)	0.0668 (12)
H9A	−0.2261	0.4820	0.4885	0.080*
H9B	−0.2155	0.4219	0.6694	0.080*
C10	0.3056 (3)	0.3589 (3)	−0.1909 (7)	0.0667 (12)
C11	−0.1385 (2)	0.3919 (3)	0.4654 (6)	0.0639 (11)
H11A	−0.0927	0.4272	0.5202	0.077*
H11B	−0.1278	0.3368	0.5182	0.077*
C12	−0.2964 (2)	0.3765 (3)	0.4368 (6)	0.0594 (11)
H12A	−0.2903	0.3197	0.4858	0.071*
C13	0.1385 (3)	0.3435 (2)	−0.3521 (5)	0.0519 (10)
H13A	0.0829	0.3375	−0.4057	0.062*
C14	−0.0656 (2)	0.3531 (2)	0.1735 (5)	0.0489 (9)
C15	0.2426 (2)	0.3815 (2)	−0.0817 (6)	0.0525 (10)
C16	−0.1424 (2)	0.3893 (2)	0.2434 (5)	0.0491 (9)
H16A	−0.1494	0.4459	0.1934	0.059*
C17	0.1590 (2)	0.3722 (2)	−0.1597 (5)	0.0438 (9)
C18	0.0941 (2)	0.3959 (2)	−0.0379 (5)	0.0432 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0567 (17)	0.097 (2)	0.0653 (19)	−0.0119 (16)	0.0002 (14)	−0.0117 (16)
O2	0.078 (2)	0.0557 (17)	0.084 (2)	0.0235 (15)	0.0142 (16)	0.0192 (15)
O3	0.0640 (16)	0.0435 (14)	0.0507 (15)	−0.0001 (12)	0.0089 (12)	−0.0073 (12)
N1	0.0474 (18)	0.0430 (17)	0.065 (2)	−0.0004 (14)	0.0150 (15)	−0.0112 (14)
N2	0.0483 (18)	0.0446 (17)	0.063 (2)	0.0103 (14)	0.0156 (15)	0.0052 (15)
C1	0.052 (4)	0.062 (15)	0.054 (8)	0.001 (11)	0.007 (5)	−0.002 (10)
C1'	0.052 (4)	0.062 (15)	0.054 (8)	0.001 (11)	0.007 (5)	−0.002 (10)
C2	0.049 (3)	0.133 (5)	0.137 (5)	−0.003 (3)	0.021 (3)	0.000 (4)
C3	0.066 (3)	0.111 (4)	0.078 (3)	0.003 (3)	0.026 (2)	−0.003 (3)
C4	0.052 (2)	0.114 (4)	0.060 (3)	0.003 (2)	0.005 (2)	−0.012 (2)
C5	0.089 (4)	0.182 (7)	0.091 (4)	−0.019 (4)	0.029 (3)	−0.020 (4)
C6	0.055 (2)	0.094 (3)	0.060 (2)	−0.002 (2)	0.0059 (19)	−0.022 (2)
C7	0.091 (3)	0.052 (2)	0.060 (2)	−0.007 (2)	0.028 (2)	−0.0087 (19)
C8	0.077 (3)	0.061 (3)	0.087 (3)	0.001 (2)	0.041 (3)	−0.007 (2)
C9	0.066 (3)	0.080 (3)	0.056 (2)	−0.004 (2)	0.013 (2)	−0.015 (2)
C10	0.052 (2)	0.064 (3)	0.087 (3)	−0.0014 (19)	0.021 (2)	0.004 (2)
C11	0.055 (2)	0.079 (3)	0.057 (2)	−0.007 (2)	0.0021 (19)	−0.006 (2)
C12	0.059 (2)	0.062 (2)	0.058 (2)	−0.0005 (19)	0.0116 (19)	0.0021 (19)
C13	0.062 (2)	0.042 (2)	0.052 (2)	−0.0038 (17)	0.0107 (18)	−0.0033 (16)
C14	0.050 (2)	0.039 (2)	0.058 (2)	0.0026 (17)	0.0056 (17)	0.0026 (17)
C15	0.051 (2)	0.049 (2)	0.058 (2)	−0.0037 (17)	0.0101 (18)	0.0030 (17)
C16	0.052 (2)	0.043 (2)	0.053 (2)	0.0033 (16)	0.0103 (17)	0.0060 (16)
C17	0.049 (2)	0.0339 (18)	0.050 (2)	−0.0022 (15)	0.0113 (16)	0.0022 (15)
C18	0.052 (2)	0.0313 (17)	0.046 (2)	0.0023 (15)	0.0077 (16)	0.0037 (16)

Geometric parameters (Å, º) top

O1—C15	1.360 (5)	C4—H4B	0.9700
O1—H1B	0.8200	C5—H5A	0.9600
O2—C14	1.220 (4)	C5—H5B	0.9600
O3—C18	1.239 (4)	C5—H5C	0.9600
N1—C18	1.342 (5)	C6—C16	1.527 (6)
N1—N2	1.382 (4)	C6—H6A	0.9700
N1—H1A	0.8600	C6—H6B	0.9700
N2—C14	1.346 (5)	C7—C13	1.376 (6)
N2—H2A	0.8600	C7—C8	1.378 (7)
C1—C3	1.50 (4)	C7—H7A	0.9300
C1—H1C	0.9600	C8—C10	1.372 (6)
C1—H1D	0.9600	C8—H8A	0.9300
C1—H1E	0.9600	C9—C11	1.525 (6)
C1'—C3	1.63 (4)	C9—C12	1.526 (6)
C1'—H1'A	0.9600	C9—H9A	0.9700
C1'—H1'B	0.9600	C9—H9B	0.9700
C1'—H1'C	0.9600	C10—C15	1.394 (6)
C2—C10	1.518 (7)	C11—C16	1.515 (5)
C2—H2B	0.9600	C11—H11A	0.9700
C2—H2C	0.9600	C11—H11B	0.9700
C2—H2D	0.9600	C12—H12A	0.9800
C3—C5	1.469 (7)	C13—C17	1.395 (5)
C3—C12	1.554 (6)	C13—H13A	0.9300
C3—H3A	0.9800	C14—C16	1.511 (5)
C4—C12	1.512 (6)	C15—C17	1.395 (5)
C4—C6	1.514 (6)	C16—H16A	0.9800
C4—H4A	0.9700	C17—C18	1.479 (5)

C15—O1—H1B	109.5	H6A—C6—H6B	107.9
C18—N1—N2	119.8 (3)	C13—C7—C8	119.2 (4)
C18—N1—H1A	120.1	C13—C7—H7A	120.4
N2—N1—H1A	120.1	C8—C7—H7A	120.4
C14—N2—N1	122.1 (3)	C10—C8—C7	122.6 (4)
C14—N2—H2A	118.9	C10—C8—H8A	118.7
N1—N2—H2A	118.9	C7—C8—H8A	118.7
C3—C1—H1C	109.5	C11—C9—C12	113.4 (3)
C3—C1—H1D	109.5	C11—C9—H9A	108.9
C3—C1—H1E	109.5	C12—C9—H9A	108.9
C3—C1'—H1'A	109.5	C11—C9—H9B	108.9
C3—C1'—H1'B	109.5	C12—C9—H9B	108.9
H1'A—C1'—H1'B	109.5	H9A—C9—H9B	107.7
C3—C1'—H1'C	109.5	C8—C10—C15	118.0 (4)
H1'A—C1'—H1'C	109.5	C8—C10—C2	122.8 (4)
H1'B—C1'—H1'C	109.5	C15—C10—C2	119.2 (4)
C10—C2—H2B	109.5	C16—C11—C9	111.7 (3)
C10—C2—H2C	109.5	C16—C11—H11A	109.3
H2B—C2—H2C	109.5	C9—C11—H11A	109.3
C10—C2—H2D	109.5	C16—C11—H11B	109.3
H2B—C2—H2D	109.5	C9—C11—H11B	109.3
H2C—C2—H2D	109.5	H11A—C11—H11B	107.9
C5—C3—C1	112.2 (16)	C4—C12—C9	109.0 (4)
C5—C3—C12	112.8 (4)	C4—C12—C3	112.2 (4)
C1—C3—C12	115.8 (16)	C9—C12—C3	112.9 (4)
C5—C3—C1'	104.6 (14)	C4—C12—H12A	107.5
C1—C3—C1'	17.0 (13)	C9—C12—H12A	107.5
C12—C3—C1'	107.9 (14)	C3—C12—H12A	107.5
C5—C3—H3A	104.9	C7—C13—C17	120.1 (4)
C1—C3—H3A	104.9	C7—C13—H13A	119.9
C12—C3—H3A	104.9	C17—C13—H13A	119.9
C1'—C3—H3A	121.9	O2—C14—N2	122.3 (3)
C12—C4—C6	112.4 (4)	O2—C14—C16	124.3 (3)
C12—C4—H4A	109.1	N2—C14—C16	113.3 (3)
C6—C4—H4A	109.1	O1—C15—C10	117.2 (4)
C12—C4—H4B	109.1	O1—C15—C17	122.1 (3)
C6—C4—H4B	109.1	C10—C15—C17	120.6 (4)
H4A—C4—H4B	107.8	C14—C16—C11	114.0 (3)
C3—C5—H5A	109.5	C14—C16—C6	108.9 (3)
C3—C5—H5B	109.5	C11—C16—C6	109.1 (3)
H5A—C5—H5B	109.5	C14—C16—H16A	108.2
C3—C5—H5C	109.5	C11—C16—H16A	108.2
H5A—C5—H5C	109.5	C6—C16—H16A	108.2
H5B—C5—H5C	109.5	C15—C17—C13	119.4 (3)
C4—C6—C16	111.9 (4)	C15—C17—C18	118.9 (3)
C4—C6—H6A	109.2	C13—C17—C18	121.7 (3)
C16—C6—H6A	109.2	O3—C18—N1	121.5 (3)
C4—C6—H6B	109.2	O3—C18—C17	122.0 (3)
C16—C6—H6B	109.2	N1—C18—C17	116.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2ⁱ	0.86	2.05	2.821 (4)	149
O1—H1B···O3	0.82	1.92	2.636 (4)	145
N2—H2A···O3ⁱⁱ	0.86	2.10	2.898 (4)	154

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

Experimental details

Crystal data
Chemical formula	C₁₈H₂₆N₂O₃
M_r	318.41
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	16.193 (5), 16.194 (5), 6.856 (2)
β (°)	97.892 (4)
V (Å³)	1780.8 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.43 × 0.26 × 0.22

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8728, 6453, 3925
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.756

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.080, 0.211, 1.05
No. of reflections	6453
No. of parameters	217
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.60

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2ⁱ	0.8598	2.0489	2.821 (4)	149.02
O1—H1B···O3	0.8196	1.9213	2.636 (4)	145.12
N2—H2A···O3ⁱⁱ	0.8603	2.1024	2.898 (4)	153.59

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

Acknowledgements

This project was sponsored by the K. C. Wong Magna Fund of Ningbo University and Ningbo Municipal Natural Science Foundation (2008 A610051)

References

Alexiou, M., Dendrinou-Samara, C., Raptopoulou, C. P., Terzis, A. & Kessissoglou, D. P. (2002). Inorg. Chem. 41, 4732–4738. Web of Science CSD CrossRef PubMed CAS Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Gaynor, D., Starikova, Z. A., Ostrovsky, S., Haase, W. & Nolan, K. B. (2002). Chem. Commun. pp. 506–507. Web of Science CSD CrossRef Google Scholar
Lah, M. S. & Pecoraro, V. L. (1989). J. Am. Chem. Soc. 111, 7258–7259. CSD CrossRef CAS Web of Science Google Scholar
Lehaire, M. L., Scopelliti, R., Piotrowski, H. & Severin, K. (2002). Angew. Chem. Int. Ed. 41, 1419–1421. CrossRef CAS Google Scholar
Liu, W., Lee, K., Park, M., John, R. P., Moon, D., Zou, Y., Liu, X., Ri, H.-C., Kim, G. H. & Lah, M. S. (2008). Inorg. Chem. 47, 8807–8812. Web of Science CSD CrossRef PubMed CAS Google Scholar
Liu, S. X., Lin, S., Lin, B. Z., Lin, C. C. & Huang, J. Q. (2001). Angew. Chem. Int. Ed. 40, 1084–1087. CrossRef CAS Google Scholar
Saalfrank, R. W., Bernt, I., Chowdhry, M. M., Hampel, F. & Vaughan, G. B. M. (2001). Chem. Eur. J. 7, 2765–2768. CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar