N′-Ferrocenyl-2-hydroxy­benzohydrazide

Xu, Y.; Chen, C.-L.; Zhou, J.; Li, M.-X.

doi:10.1107/S1600536807065634

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page m177

https://doi.org/10.1107/S1600536807065634

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N′-Ferrocenyl-2-hydroxybenzohydrazide

Ying Xu,^a Chun-Ling Chen,^a Jing Zhou ^a and Ming-Xue Li ^a ^*

^aInstitute of Molecular and Crystal Engineering, College of Chemistry and Chemical Engineering, Henan University, Kaifeng 475001, People's Republic of China
^*Correspondence e-mail: limingxue@henu.edu.cn

(Received 13 November 2007; accepted 5 December 2007; online 12 December 2007)

The title complex, [Fe(C₅H₅)(C₁₃H₁₁N₂O₃)], was prepared via self-assembly using ferrocenyl hydrazide and ethyl salicylate. The compound is potentially a tridentate ferrocene-based ligand. The conformation of the molecule allows the formation of an intramolecular N—H⋯O hydrogen bond involving the hydroxyl group. The CONHNHCO unit and the rings bonded to it are nearly coplanar. The crystal structure is stabilized by intermolecular O—H⋯O(carbonyl) and N—H⋯O(carbonyl) hydrogen bonds.

Related literature

For related literature about applications of ferrocene complexes, see: Beer (1992 ); Beer & Smith (1997 ); Long (1995 ); Miller & Epstein (1994 ); Nguyen et al. (1999 ).

Experimental

Crystal data

[Fe(C₅H₅)(C₁₃H₁₁N₂O₃)]
M_r = 364.18
Monoclinic, C 2/c
a = 20.680 (3) Å
b = 9.9673 (15) Å
c = 16.941 (3) Å
β = 121.704 (3)°
V = 2970.8 (8) Å³
Z = 8
Mo Kα radiation
μ = 1.03 mm⁻¹
T = 293 (2) K
0.20 × 0.18 × 0.16 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.820, T_max = 0.852
7479 measured reflections
2611 independent reflections
1053 reflections with I > 2σ(I)
R_int = 0.129

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.086
S = 0.57
2611 reflections
230 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯O3	0.860 (10)	1.95 (2)	2.631 (4)	135 (3)
O3—H3B⋯O1ⁱ	0.822 (10)	1.908 (15)	2.705 (4)	163 (4)
N1—H1B⋯O2ⁱⁱ	0.871 (10)	2.03 (2)	2.810 (4)	148 (4)
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x+2, y, -z+{\script{3\over 2}}]$ .

Data collection: SMART (Bruker, 2000); cell refinement: SAINT-Plus (Bruker, 2000); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536807065634/bh2153sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807065634/bh2153Isup2.hkl

checkCIF report

Comment top

The synthesis, isolation and characterization of ferrocene in 1951 marked an important milestone in the evolution of modern organometallic chemistry. Potential applications in material sciences, such as molecular sensors (Beer, 1992; Beer & Smith, 1997), molecular magnetic materials (Miller & Epstein, 1994), and nonlinear optical materials (Nguyen et al., 1999; Long, 1995) attracted much attention. We report here the crystal structure of the title compound, (I), a new ferrocene-based complex (Fig. 1).

The title compound belongs to space group C2/c. The bond lengths O1?C11 and O2?C12 are 1.240 (5) and 1.233 (4) Å, respectively, as excepted for double bonds. The bond length O3—C18, 1.349 (5) Å, corresponds to a single bond. The N1—C11 and N2—C12 bond distances are 1.340 (5) and 1.343 (5) Å, respectively, which make clear they are in the normal range for N—C single bonds. The bond length N1—N2 = 1.381 (4) Å is also consistent with a single N—N bond. An intramolecular N2—H2B···O3 hydrogen bond is observed in the molecular structure.

In the crystal, molecules are connected by intermolecular hydrogen bonds involving carbonyl O atoms O2 and O3 as acceptor and N—H or O—H groups as donors.

Related literature top

For related literature about applications of ferrocene complexes, see: Beer (1992); Beer & Smith (1997); Long (1995); Miller & Epstein (1994); Nguyen et al. (1999).

Experimental top

All reagents were commercially available and of analytical grade. Ferrocenyl hydrazide (1.22 g, 5 mmol) and ethyl salicylate (0.83 g, 5 mmol) were mixed in ethanol and refluxed for 7 h. The resulting red solid was filtered, washed with ethanol and dried under reduced pressure. Anal. Calc. for C₁₈H₁₆FeN₂O₃: C 59.37, H 4.43, N 7.69%. Found: C 59.48, H 4.31, N 7.52%.

Structure description top

In the crystal, molecules are connected by intermolecular hydrogen bonds involving carbonyl O atoms O2 and O3 as acceptor and N—H or O—H groups as donors.

For related literature about applications of ferrocene complexes, see: Beer (1992); Beer & Smith (1997); Long (1995); Miller & Epstein (1994); Nguyen et al. (1999).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT-Plus (Bruker, 2000); data reduction: SAINT-Plus (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997a).

Figures top

Fig. 1. The molecular structure of (I) with displacement ellipsoids drawn at the 50% probability level.

N'-Ferrocenyl-2-hydroxybenzohydrazide top

Crystal data top

[Fe(C₅H₅)(C₁₃H₁₁N₂O₃)]	F(000) = 1504
M_r = 364.18	D_x = 1.628 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 397 reflections
a = 20.680 (3) Å	θ = 2.3–28.0°
b = 9.9673 (15) Å	µ = 1.04 mm⁻¹
c = 16.941 (3) Å	T = 293 K
β = 121.704 (3)°	Block, red
V = 2970.8 (8) Å³	0.20 × 0.18 × 0.16 mm
Z = 8

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2611 independent reflections
Radiation source: fine-focus sealed tube	1053 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.129
0.3° wide ω scans	θ_max = 25.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −24→18
T_min = 0.820, T_max = 0.852	k = −11→11
7479 measured reflections	l = −20→20

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.086	H atoms treated by a mixture of independent and constrained refinement
S = 0.57	w = 1/[σ²(F_o²) + (0.02P)²] where P = (F_o² + 2F_c²)/3
2611 reflections	(Δ/σ)_max < 0.001
230 parameters	Δρ_max = 0.48 e Å⁻³
3 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

[Fe(C₅H₅)(C₁₃H₁₁N₂O₃)]	V = 2970.8 (8) Å³
M_r = 364.18	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 20.680 (3) Å	µ = 1.04 mm⁻¹
b = 9.9673 (15) Å	T = 293 K
c = 16.941 (3) Å	0.20 × 0.18 × 0.16 mm
β = 121.704 (3)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2611 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	1053 reflections with I > 2σ(I)
T_min = 0.820, T_max = 0.852	R_int = 0.129
7479 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	3 restraints
wR(F²) = 0.086	H atoms treated by a mixture of independent and constrained refinement
S = 0.57	Δρ_max = 0.48 e Å⁻³
2611 reflections	Δρ_min = −0.34 e Å⁻³
230 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Fe1	0.94540 (4)	0.77786 (6)	0.86429 (4)	0.03507 (19)
O1	0.83150 (16)	0.4726 (3)	0.79890 (19)	0.0410 (9)
O2	0.92978 (15)	0.2865 (3)	0.63670 (17)	0.0437 (8)
O3	0.75985 (16)	0.1341 (3)	0.6733 (2)	0.0417 (8)
H3B	0.7289 (10)	0.099 (3)	0.683 (2)	0.060 (9)*
N1	0.9235 (2)	0.3971 (3)	0.7765 (2)	0.0308 (10)
H1B	0.9700 (8)	0.387 (4)	0.790 (2)	0.058 (16)*
N2	0.87479 (18)	0.2969 (4)	0.7205 (2)	0.0340 (9)
H2B	0.8365 (9)	0.276 (3)	0.7248 (17)	0.034 (5)*
C1	0.8498 (3)	0.8152 (5)	0.7406 (3)	0.0489 (14)
H1A	0.8151	0.7473	0.6970	0.059*
C2	0.8456 (3)	0.8730 (4)	0.8133 (3)	0.0432 (13)
H2A	0.8071	0.8530	0.8287	0.052*
C3	0.9052 (3)	0.9656 (4)	0.8594 (3)	0.0451 (14)
H3A	0.9161	1.0216	0.9126	0.054*
C4	0.9463 (3)	0.9629 (4)	0.8144 (3)	0.0454 (14)
H4A	0.9919	1.0160	0.8322	0.055*
C5	0.9131 (3)	0.8688 (5)	0.7419 (3)	0.0529 (15)
H5A	0.9302	0.8462	0.6995	0.064*
C6	1.0186 (3)	0.6269 (4)	0.8847 (3)	0.0376 (13)
H6A	1.0360	0.6011	0.8430	0.045*
C7	1.0541 (2)	0.7191 (4)	0.9589 (3)	0.0415 (13)
H7A	1.1002	0.7706	0.9767	0.050*
C8	1.0106 (3)	0.7288 (4)	1.0008 (3)	0.0444 (13)
H8A	1.0216	0.7865	1.0533	0.053*
C9	0.9489 (3)	0.6410 (4)	0.9538 (3)	0.0337 (12)
H9A	0.9093	0.6261	0.9681	0.040*
C10	0.9534 (3)	0.5776 (4)	0.8825 (3)	0.0304 (12)
C11	0.8976 (3)	0.4797 (4)	0.8161 (3)	0.0302 (12)
C12	0.8800 (2)	0.2468 (4)	0.6504 (3)	0.0272 (11)
C13	0.8246 (2)	0.1417 (4)	0.5917 (3)	0.0269 (11)
C14	0.8305 (3)	0.0933 (4)	0.5195 (3)	0.0388 (13)
H14A	0.8674	0.1284	0.5097	0.047*
C15	0.7828 (3)	−0.0064 (4)	0.4615 (3)	0.0490 (15)
H15A	0.7875	−0.0372	0.4129	0.059*
C16	0.7285 (3)	−0.0601 (4)	0.4754 (3)	0.0422 (14)
H16A	0.6968	−0.1283	0.4371	0.051*
C17	0.7214 (2)	−0.0123 (4)	0.5463 (3)	0.0375 (13)
H17A	0.6845	−0.0485	0.5556	0.045*
C18	0.7675 (3)	0.0877 (4)	0.6038 (3)	0.0300 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.0332 (4)	0.0339 (3)	0.0390 (4)	0.0019 (4)	0.0195 (3)	−0.0003 (4)
O1	0.0258 (18)	0.0442 (19)	0.058 (2)	−0.0049 (17)	0.0251 (17)	−0.0128 (15)
O2	0.0409 (17)	0.061 (2)	0.0440 (17)	−0.0154 (18)	0.0328 (15)	−0.0120 (16)
O3	0.0369 (18)	0.052 (2)	0.0518 (19)	−0.0128 (17)	0.0345 (16)	−0.0080 (16)
N1	0.026 (2)	0.029 (2)	0.043 (2)	0.000 (2)	0.022 (2)	−0.0085 (17)
N2	0.029 (2)	0.038 (2)	0.043 (2)	−0.005 (2)	0.0246 (18)	−0.0056 (19)
C1	0.043 (3)	0.058 (3)	0.031 (3)	0.006 (3)	0.010 (3)	0.001 (2)
C2	0.044 (3)	0.037 (3)	0.056 (3)	0.013 (3)	0.031 (3)	0.010 (2)
C3	0.049 (3)	0.031 (3)	0.059 (3)	−0.007 (3)	0.031 (3)	−0.007 (2)
C4	0.042 (3)	0.036 (3)	0.066 (4)	0.002 (3)	0.034 (3)	0.011 (3)
C5	0.051 (3)	0.069 (4)	0.048 (3)	0.019 (3)	0.032 (3)	0.021 (3)
C6	0.033 (3)	0.044 (3)	0.033 (3)	0.010 (3)	0.016 (2)	−0.003 (2)
C7	0.021 (2)	0.033 (3)	0.048 (3)	0.011 (3)	0.002 (2)	0.005 (3)
C8	0.049 (3)	0.039 (3)	0.040 (3)	0.000 (3)	0.020 (3)	−0.006 (2)
C9	0.039 (3)	0.029 (3)	0.038 (3)	0.002 (2)	0.024 (2)	−0.002 (2)
C10	0.028 (3)	0.027 (2)	0.037 (3)	−0.001 (2)	0.018 (2)	−0.005 (2)
C11	0.033 (3)	0.028 (3)	0.027 (3)	0.001 (3)	0.013 (2)	0.003 (2)
C12	0.024 (2)	0.030 (3)	0.031 (2)	0.005 (2)	0.016 (2)	0.008 (2)
C13	0.025 (3)	0.023 (2)	0.032 (3)	0.000 (2)	0.014 (2)	0.002 (2)
C14	0.038 (3)	0.042 (3)	0.046 (3)	0.000 (3)	0.028 (3)	0.000 (2)
C15	0.052 (4)	0.056 (3)	0.045 (3)	−0.006 (3)	0.030 (3)	−0.014 (3)
C16	0.038 (3)	0.043 (3)	0.044 (3)	−0.017 (3)	0.021 (3)	−0.019 (2)
C17	0.033 (3)	0.040 (3)	0.041 (3)	−0.012 (2)	0.020 (3)	−0.007 (2)
C18	0.034 (3)	0.030 (3)	0.031 (3)	0.005 (2)	0.020 (2)	0.002 (2)

Geometric parameters (Å, º) top

Fe1—C2	2.008 (4)	C3—H3A	0.9800
Fe1—C9	2.013 (4)	C4—C5	1.405 (6)
Fe1—C10	2.014 (4)	C4—H4A	0.9800
Fe1—C1	2.021 (4)	C5—H5A	0.9800
Fe1—C5	2.028 (5)	C6—C7	1.412 (5)
Fe1—C6	2.031 (4)	C6—C10	1.416 (6)
Fe1—C3	2.031 (4)	C6—H6A	0.9800
Fe1—C8	2.031 (4)	C7—C8	1.412 (6)
Fe1—C4	2.033 (4)	C7—H7A	0.9800
Fe1—C7	2.045 (4)	C8—C9	1.400 (5)
O1—C11	1.240 (5)	C8—H8A	0.9800
O2—C12	1.233 (4)	C9—C10	1.410 (5)
O3—C18	1.349 (5)	C9—H9A	0.9800
O3—H3B	0.822 (10)	C10—C11	1.478 (5)
N1—C11	1.340 (5)	C12—C13	1.484 (5)
N1—N2	1.381 (4)	C13—C14	1.379 (6)
N1—H1B	0.871 (10)	C13—C18	1.407 (6)
N2—C12	1.343 (5)	C14—C15	1.381 (5)
N2—H2B	0.860 (10)	C14—H14A	0.9300
C1—C5	1.402 (6)	C15—C16	1.373 (6)
C1—C2	1.404 (6)	C15—H15A	0.9300
C1—H1A	0.9800	C16—C17	1.370 (6)
C2—C3	1.403 (6)	C16—H16A	0.9300
C2—H2A	0.9800	C17—C18	1.369 (5)
C3—C4	1.410 (6)	C17—H17A	0.9300

C2—Fe1—C9	105.43 (18)	C4—C3—H3A	126.6
C2—Fe1—C10	121.17 (19)	Fe1—C3—H3A	126.6
C9—Fe1—C10	41.01 (16)	C5—C4—C3	109.2 (4)
C2—Fe1—C1	40.79 (16)	C5—C4—Fe1	69.5 (3)
C9—Fe1—C1	122.31 (19)	C3—C4—Fe1	69.6 (3)
C10—Fe1—C1	107.34 (18)	C5—C4—H4A	125.4
C2—Fe1—C5	68.7 (2)	C3—C4—H4A	125.4
C9—Fe1—C5	159.32 (19)	Fe1—C4—H4A	125.4
C10—Fe1—C5	123.77 (19)	C1—C5—C4	107.0 (5)
C1—Fe1—C5	40.53 (17)	C1—C5—Fe1	69.5 (3)
C2—Fe1—C6	158.24 (18)	C4—C5—Fe1	70.0 (3)
C9—Fe1—C6	68.96 (18)	C1—C5—H5A	126.5
C10—Fe1—C6	40.98 (16)	C4—C5—H5A	126.5
C1—Fe1—C6	123.23 (18)	Fe1—C5—H5A	126.5
C5—Fe1—C6	108.72 (19)	C7—C6—C10	107.0 (4)
C2—Fe1—C3	40.66 (16)	C7—C6—Fe1	70.3 (2)
C9—Fe1—C3	120.45 (18)	C10—C6—Fe1	68.9 (2)
C10—Fe1—C3	156.7 (2)	C7—C6—H6A	126.5
C1—Fe1—C3	68.42 (18)	C10—C6—H6A	126.5
C5—Fe1—C3	68.83 (19)	Fe1—C6—H6A	126.5
C6—Fe1—C3	160.36 (19)	C8—C7—C6	108.7 (4)
C2—Fe1—C8	121.38 (19)	C8—C7—Fe1	69.2 (2)
C9—Fe1—C8	40.51 (16)	C6—C7—Fe1	69.2 (2)
C10—Fe1—C8	68.62 (17)	C8—C7—H7A	125.6
C1—Fe1—C8	158.0 (2)	C6—C7—H7A	125.6
C5—Fe1—C8	159.5 (2)	Fe1—C7—H7A	125.6
C6—Fe1—C8	68.81 (18)	C9—C8—C7	107.6 (4)
C3—Fe1—C8	106.29 (19)	C9—C8—Fe1	69.0 (2)
C2—Fe1—C4	67.96 (18)	C7—C8—Fe1	70.2 (2)
C9—Fe1—C4	157.47 (19)	C9—C8—H8A	126.2
C10—Fe1—C4	160.9 (2)	C7—C8—H8A	126.2
C1—Fe1—C4	67.63 (19)	Fe1—C8—H8A	126.2
C5—Fe1—C4	40.48 (17)	C8—C9—C10	108.4 (4)
C6—Fe1—C4	125.03 (19)	C8—C9—Fe1	70.5 (2)
C3—Fe1—C4	40.59 (17)	C10—C9—Fe1	69.5 (2)
C8—Fe1—C4	123.09 (19)	C8—C9—H9A	125.8
C2—Fe1—C7	158.59 (19)	C10—C9—H9A	125.8
C9—Fe1—C7	68.03 (18)	Fe1—C9—H9A	125.8
C10—Fe1—C7	68.14 (18)	C9—C10—C6	108.2 (4)
C1—Fe1—C7	159.89 (19)	C9—C10—C11	124.8 (4)
C5—Fe1—C7	124.4 (2)	C6—C10—C11	127.0 (4)
C6—Fe1—C7	40.55 (15)	C9—C10—Fe1	69.5 (2)
C3—Fe1—C7	123.62 (18)	C6—C10—Fe1	70.2 (2)
C8—Fe1—C7	40.54 (16)	C11—C10—Fe1	124.7 (3)
C4—Fe1—C7	109.83 (19)	O1—C11—N1	121.9 (4)
C18—O3—H3B	120 (3)	O1—C11—C10	122.7 (4)
C11—N1—N2	116.7 (4)	N1—C11—C10	115.3 (4)
C11—N1—H1B	128 (2)	O2—C12—N2	120.7 (4)
N2—N1—H1B	114 (2)	O2—C12—C13	121.8 (4)
C12—N2—N1	120.5 (3)	N2—C12—C13	117.6 (4)
C12—N2—H2B	119 (2)	C14—C13—C18	117.9 (4)
N1—N2—H2B	120 (2)	C14—C13—C12	116.4 (4)
C5—C1—C2	108.5 (4)	C18—C13—C12	125.7 (4)
C5—C1—Fe1	70.0 (3)	C13—C14—C15	121.4 (5)
C2—C1—Fe1	69.1 (3)	C13—C14—H14A	119.3
C5—C1—H1A	125.7	C15—C14—H14A	119.3
C2—C1—H1A	125.7	C16—C15—C14	120.1 (5)
Fe1—C1—H1A	125.7	C16—C15—H15A	120.0
C3—C2—C1	108.5 (4)	C14—C15—H15A	120.0
C3—C2—Fe1	70.6 (3)	C17—C16—C15	119.3 (4)
C1—C2—Fe1	70.1 (3)	C17—C16—H16A	120.3
C3—C2—H2A	125.8	C15—C16—H16A	120.3
C1—C2—H2A	125.8	C18—C17—C16	121.4 (4)
Fe1—C2—H2A	125.8	C18—C17—H17A	119.3
C2—C3—C4	106.8 (4)	C16—C17—H17A	119.3
C2—C3—Fe1	68.8 (2)	O3—C18—C17	120.8 (4)
C4—C3—Fe1	69.8 (3)	O3—C18—C13	119.2 (4)
C2—C3—H3A	126.6	C17—C18—C13	120.0 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O3	0.86 (1)	1.95 (2)	2.631 (4)	135 (3)
O3—H3B···O1ⁱ	0.82 (1)	1.91 (2)	2.705 (4)	163 (4)
N1—H1B···O2ⁱⁱ	0.87 (1)	2.03 (2)	2.810 (4)	148 (4)

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

Experimental details

Crystal data
Chemical formula	[Fe(C₅H₅)(C₁₃H₁₁N₂O₃)]
M_r	364.18
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	20.680 (3), 9.9673 (15), 16.941 (3)
β (°)	121.704 (3)
V (Å³)	2970.8 (8)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.04
Crystal size (mm)	0.20 × 0.18 × 0.16

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.820, 0.852
No. of measured, independent and observed [I > 2σ(I)] reflections	7479, 2611, 1053
R_int	0.129
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.086, 0.57
No. of reflections	2611
No. of parameters	230
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.34

Computer programs: SMART (Bruker, 2000), SAINT-Plus (Bruker, 2000), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O3	0.860 (10)	1.95 (2)	2.631 (4)	135 (3)
O3—H3B···O1ⁱ	0.822 (10)	1.908 (15)	2.705 (4)	163 (4)
N1—H1B···O2ⁱⁱ	0.871 (10)	2.03 (2)	2.810 (4)	148 (4)

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

Acknowledgements

This work was financially supported by the Foundation of the Educational Department of Henan Province (No. 2007150012).

References

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