Bis(2,2′,2′′-nitrilo­triacetamide-κ3O,N,O′)cobalt(II) dinitrate tetra­hydrate

Ran, J.-W.; Pei, J.

doi:10.1107/S1600536813012968

metal-organic compounds

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Volume 69| Part 6| June 2013| Page m325

doi:10.1107/S1600536813012968

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Bis(2,2′,2′′-nitrilotriacetamide-κ³O,N,O′)cobalt(II) dinitrate tetrahydrate

Jing-Wen Ran ^a ^* and Jun Pei ^b

^aCollege of Chemical Engineering, Huanggang Normal University, Huanggang 438000, People's Republic of China, and ^bCollege of Education Science and Technology, Huanggang Normal University, Huanggang 438000, People's Republic of China
^*Correspondence e-mail: ranjw@126.com

(Received 21 December 2012; accepted 12 May 2013; online 18 May 2013)

In the centrosymmetric title compound, [Co(C₆H₁₂N₄O₃)₂](NO₃)₂·4H₂O, the Co^II ion, lying on an inversion center, is O,N,O′-chelated by two nitrilotriacetamide molecules, forming a distorted octahedral geometry. In the crystal, extensive O—H⋯O and N—H⋯O hydrogen bonds link the complex cations, nitrate anions and lattice water molecules into a three-dimensional network.

Related literature

For related structures, see: Kumari et al. (2012 ). For the synthesis of the ligand, see: Smith et al. (1995 ).

Experimental

Crystal data

[Co(C₆H₁₂N₄O₃)₂](NO₃)₂·4H₂O
M_r = 631.41
Triclinic, $[P \overline 1]$
a = 8.4910 (17) Å
b = 9.1410 (18) Å
c = 9.2580 (19) Å
α = 91.55 (3)°
β = 96.03 (3)°
γ = 110.68 (3)°
V = 667.0 (2) Å³
Z = 1
Mo Kα radiation
μ = 0.73 mm⁻¹
T = 293 K
0.36 × 0.32 × 0.25 mm

Data collection

Siemens P4 diffractometer
Absorption correction: ψ scan (XSCANS; Siemens, 1994 ) T_min = 0.779, T_max = 0.838
3692 measured reflections
2301 independent reflections
2185 reflections with I > 2σ(I)
R_int = 0.016
2 standard reflections every 150 reflections intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.080
S = 1.05
2301 reflections
191 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O6ⁱ	0.86	2.26	3.026 (3)	149
N2—H2B⋯O3ⁱⁱ	0.86	1.96	2.816 (2)	173
N3—H3C⋯O8ⁱⁱⁱ	0.86	2.11	2.958 (3)	168
N3—H3D⋯O5ⁱⁱ	0.86	2.16	3.001 (3)	166
N4—H4A⋯O7^iv	0.86	2.20	2.992 (3)	152
N4—H4B⋯O7	0.86	2.30	3.045 (3)	145
O7—H7A⋯O6	0.88 (2)	2.05 (2)	2.877 (3)	156 (3)
O7—H7B⋯O8^v	0.87 (2)	1.96 (2)	2.826 (3)	176 (3)
O8—H8A⋯O1ⁱ	0.85 (2)	2.14 (2)	2.976 (2)	166 (3)
O8—H8B⋯O6	0.85 (2)	2.16 (2)	2.980 (3)	161 (3)
O8—H8B⋯O5	0.85 (2)	2.42 (3)	3.078 (3)	134 (3)
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) -x+1, -y, -z+2; (iii) x+1, y, z+1; (iv) -x+1, -y, -z+1; (v) -x+1, -y+1, -z+1.

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: XSCANS; 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 I, global. DOI: 10.1107/S1600536813012968/hy2611sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813012968/hy2611Isup2.hkl

checkCIF report

Comment top

Transition metal compounds have been of great interest for many years. They are very important in the development of coordination chemistry. As an extension of work on the structural characterization of Co compounds, we report here the crystal structure of a new mononuclear cobalt(II) compound.

The title compound consists of a [Co(NTA)₂]²⁺ cation (NTA = nitrilotriacetamide), two nitrate anions and four solvent water molecules. The Co^II atom has a distorted octahedral coordination environment (Fig. 1), which is centrosymmetric as the Co^II atom occupies an inversion center. In the equatorial plane, the Co—N1 distance is 2.1696 (16) Å and the Co—O1 distance is 2.1057 (14) Å. The axial Co—O2 bond is appreciably shortened, which is 2.0329 (14) Å. In the crystal, extensive O—H···O and N—H···O hydrogen bonds (Table 1) link the complex cations, nitrate anions and lattice water molecules into a three-dimensional network (Fig. 2).

Related literature top

For related structures, see: Kumari et al. (2012). For the synthesis of the ligand, see: Smith et al. (1995).

Experimental top

The ligand was prepared according to the literature method (Smith et al., 1995). The title compound was synthesized by adding water solution of Co(NO₃)₂.6H₂O (291 mg, 2 mmol) to a solution of the ligand (752 mg, 4 mmol) in methanol/water (v/v 3:1, 20 ml). The mixture was stirred for 30 min at room temperature. The solution was filtered and the filtrate was allowed to stand in air for 1 week, and pink crystals were formed at the bottom of the vessel on slow evaporation of the solvent at room temperature (yield: 30%).

Computing details top

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS (Siemens, 1994); data reduction: XSCANS (Siemens, 1994); 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 molecular structure of the complex cation in the title compound. Displacement ellipsoids are drawn at the 30% probability level. [Symmetry code: (A) 2-x, 1-y, 2-z.]
	Fig. 2. The packing diagram for the title compound, viewed down the a axis, with hydrogen bonds drawn as dashed lines.

Bis(2,2',2''-nitrilotriacetamide-κ³O,N,O')cobalt(II) dinitrate tetrahydrate top

Crystal data top

[Co(C₆H₁₂N₄O₃)₂](NO₃)₂·4H₂O	Z = 1
M_r = 631.41	F(000) = 329
Triclinic, P1	D_x = 1.572 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4910 (17) Å	Cell parameters from 4804 reflections
b = 9.1410 (18) Å	θ = 2.4–28.3°
c = 9.2580 (19) Å	µ = 0.73 mm⁻¹
α = 91.55 (3)°	T = 293 K
β = 96.03 (3)°	Block, pink
γ = 110.68 (3)°	0.36 × 0.32 × 0.25 mm
V = 667.0 (2) Å³

Data collection top

Siemens P4 diffractometer	2185 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.016
Graphite monochromator	θ_max = 25.0°, θ_min = 2.2°
ω scans	h = −8→10
Absorption correction: ψ scan (XSCANS; Siemens, 1994)	k = −10→6
T_min = 0.779, T_max = 0.838	l = −11→11
3692 measured reflections	2 standard reflections every 150 reflections
2301 independent reflections	intensity decay: none

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)] = 0.028	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.080	w = 1/[σ²(F_o²) + (0.0402P)² + 0.3421P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
2301 reflections	Δρ_max = 0.32 e Å⁻³
191 parameters	Δρ_min = −0.22 e Å⁻³
6 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: 0.036 (4)

Crystal data top

[Co(C₆H₁₂N₄O₃)₂](NO₃)₂·4H₂O	γ = 110.68 (3)°
M_r = 631.41	V = 667.0 (2) Å³
Triclinic, P1	Z = 1
a = 8.4910 (17) Å	Mo Kα radiation
b = 9.1410 (18) Å	µ = 0.73 mm⁻¹
c = 9.2580 (19) Å	T = 293 K
α = 91.55 (3)°	0.36 × 0.32 × 0.25 mm
β = 96.03 (3)°

Data collection top

Siemens P4 diffractometer	2185 reflections with I > 2σ(I)
Absorption correction: ψ scan (XSCANS; Siemens, 1994)	R_int = 0.016
T_min = 0.779, T_max = 0.838	2 standard reflections every 150 reflections
3692 measured reflections	intensity decay: none
2301 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	6 restraints
wR(F²) = 0.080	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.32 e Å⁻³
2301 reflections	Δρ_min = −0.22 e Å⁻³
191 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
Co1	1.0000	0.5000	1.0000	0.02488 (14)
O1	1.04636 (18)	0.42993 (15)	1.21011 (14)	0.0357 (3)
N1	0.84838 (18)	0.25174 (17)	0.97367 (17)	0.0255 (3)
O2	0.77965 (17)	0.51316 (15)	1.05517 (16)	0.0358 (3)
N2	0.5284 (2)	0.37589 (19)	1.1249 (2)	0.0385 (4)
H2A	0.5140	0.4602	1.1531	0.046*
H2B	0.4520	0.2860	1.1335	0.046*
C2	0.6662 (2)	0.3843 (2)	1.0691 (2)	0.0279 (4)
C4	0.7310 (2)	0.0285 (2)	0.7776 (2)	0.0309 (4)
C1	0.6803 (2)	0.2307 (2)	1.0199 (2)	0.0344 (5)
H1A	0.6607	0.1616	1.0990	0.041*
H1B	0.5929	0.1810	0.9393	0.041*
C5	0.9455 (3)	0.1821 (2)	1.0737 (2)	0.0311 (4)
H5A	1.0417	0.1752	1.0298	0.037*
H5B	0.8741	0.0772	1.0931	0.037*
C6	1.0065 (2)	0.2848 (2)	1.2144 (2)	0.0320 (4)
C3	0.8369 (3)	0.2003 (2)	0.8196 (2)	0.0319 (4)
H3A	0.9508	0.2204	0.7957	0.038*
H3B	0.7894	0.2642	0.7604	0.038*
O3	0.7098 (2)	−0.07085 (16)	0.86712 (17)	0.0436 (4)
N3	1.0164 (3)	0.2180 (2)	1.3353 (2)	0.0498 (5)
H3C	1.0514	0.2739	1.4165	0.060*
H3D	0.9878	0.1178	1.3342	0.060*
N4	0.6714 (3)	−0.0027 (2)	0.6381 (2)	0.0481 (5)
H4A	0.6138	−0.0976	0.6053	0.058*
H4B	0.6903	0.0720	0.5802	0.058*
O4	0.3650 (3)	0.0756 (2)	0.7431 (3)	0.0729 (6)
N5	0.3013 (3)	0.1744 (2)	0.7124 (2)	0.0490 (5)
O6	0.3922 (3)	0.3140 (2)	0.7051 (3)	0.0790 (7)
O5	0.1443 (3)	0.1328 (2)	0.6828 (3)	0.0753 (6)
O8	0.1387 (2)	0.4513 (2)	0.58788 (17)	0.0494 (4)
O7	0.6172 (3)	0.2799 (2)	0.5059 (2)	0.0606 (5)
H8A	0.072 (4)	0.470 (4)	0.642 (3)	0.091*
H8B	0.195 (4)	0.405 (4)	0.637 (3)	0.091*
H7A	0.566 (4)	0.319 (4)	0.566 (3)	0.091*
H7B	0.689 (4)	0.364 (3)	0.475 (4)	0.091*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.0248 (2)	0.0160 (2)	0.0289 (2)	0.00148 (14)	0.00284 (14)	0.00066 (13)
O1	0.0466 (8)	0.0217 (7)	0.0305 (7)	0.0042 (6)	−0.0021 (6)	0.0001 (5)
N1	0.0247 (8)	0.0181 (7)	0.0304 (8)	0.0039 (6)	0.0024 (6)	−0.0002 (6)
O2	0.0316 (7)	0.0186 (7)	0.0550 (9)	0.0044 (6)	0.0126 (6)	0.0028 (6)
N2	0.0346 (9)	0.0217 (8)	0.0584 (11)	0.0066 (7)	0.0156 (8)	0.0010 (8)
C2	0.0262 (9)	0.0220 (9)	0.0330 (10)	0.0064 (8)	0.0018 (7)	0.0018 (7)
C4	0.0296 (10)	0.0236 (9)	0.0357 (11)	0.0052 (8)	0.0043 (8)	−0.0038 (8)
C1	0.0269 (10)	0.0204 (9)	0.0521 (12)	0.0030 (8)	0.0085 (9)	−0.0014 (8)
C5	0.0367 (10)	0.0199 (9)	0.0347 (10)	0.0091 (8)	−0.0002 (8)	0.0008 (7)
C6	0.0331 (10)	0.0254 (10)	0.0334 (10)	0.0069 (8)	−0.0013 (8)	0.0026 (8)
C3	0.0374 (11)	0.0220 (9)	0.0291 (10)	0.0025 (8)	0.0027 (8)	0.0003 (7)
O3	0.0528 (9)	0.0226 (7)	0.0426 (9)	−0.0009 (6)	0.0011 (7)	0.0011 (6)
N3	0.0765 (14)	0.0299 (9)	0.0343 (10)	0.0119 (9)	−0.0060 (9)	0.0041 (8)
N4	0.0604 (12)	0.0313 (9)	0.0387 (10)	0.0034 (9)	−0.0061 (9)	−0.0075 (8)
O4	0.0603 (12)	0.0588 (12)	0.1021 (17)	0.0247 (10)	0.0046 (11)	0.0217 (11)
N5	0.0592 (13)	0.0371 (11)	0.0523 (12)	0.0154 (10)	0.0204 (10)	0.0052 (9)
O6	0.0978 (16)	0.0309 (9)	0.0995 (16)	0.0039 (10)	0.0445 (13)	−0.0050 (10)
O5	0.0557 (12)	0.0608 (12)	0.1194 (19)	0.0294 (10)	0.0200 (12)	0.0227 (12)
O8	0.0611 (11)	0.0471 (10)	0.0394 (9)	0.0186 (8)	0.0064 (8)	0.0022 (7)
O7	0.0692 (13)	0.0430 (10)	0.0559 (11)	0.0022 (9)	0.0120 (9)	0.0010 (8)

Geometric parameters (Å, º) top

Co1—O2	2.0329 (14)	C5—C6	1.516 (3)
Co1—O1	2.1057 (14)	C5—H5A	0.9700
Co1—N1	2.1696 (16)	C5—H5B	0.9700
O1—C6	1.250 (2)	C6—N3	1.299 (3)
N1—C3	1.472 (2)	C3—H3A	0.9700
N1—C5	1.478 (2)	C3—H3B	0.9700
N1—C1	1.482 (2)	N3—H3C	0.8600
O2—C2	1.251 (2)	N3—H3D	0.8600
N2—C2	1.307 (3)	N4—H4A	0.8600
N2—H2A	0.8600	N4—H4B	0.8600
N2—H2B	0.8600	O4—N5	1.231 (3)
C2—C1	1.513 (3)	N5—O6	1.245 (3)
C4—O3	1.225 (3)	N5—O5	1.247 (3)
C4—N4	1.321 (3)	O8—H8A	0.85 (2)
C4—C3	1.524 (3)	O8—H8B	0.85 (2)
C1—H1A	0.9700	O7—H7A	0.88 (2)
C1—H1B	0.9700	O7—H7B	0.87 (2)

O2ⁱ—Co1—O2	180.0	N1—C1—C2	112.43 (15)
O2ⁱ—Co1—O1	91.39 (7)	N1—C1—H1A	109.1
O2—Co1—O1	88.61 (7)	C2—C1—H1A	109.1
O2ⁱ—Co1—O1ⁱ	88.61 (7)	N1—C1—H1B	109.1
O2—Co1—O1ⁱ	91.39 (7)	C2—C1—H1B	109.1
O1—Co1—O1ⁱ	180.0	H1A—C1—H1B	107.9
O2ⁱ—Co1—N1	98.08 (6)	N1—C5—C6	108.58 (15)
O2—Co1—N1	81.92 (6)	N1—C5—H5A	110.0
O1—Co1—N1	78.83 (6)	C6—C5—H5A	110.0
O1ⁱ—Co1—N1	101.17 (6)	N1—C5—H5B	110.0
O2ⁱ—Co1—N1ⁱ	81.92 (6)	C6—C5—H5B	110.0
O2—Co1—N1ⁱ	98.08 (6)	H5A—C5—H5B	108.4
O1—Co1—N1ⁱ	101.17 (6)	O1—C6—N3	122.53 (19)
O1ⁱ—Co1—N1ⁱ	78.83 (6)	O1—C6—C5	119.19 (17)
N1—Co1—N1ⁱ	180.00 (8)	N3—C6—C5	118.28 (17)
C6—O1—Co1	113.26 (12)	N1—C3—C4	115.74 (16)
C3—N1—C5	113.47 (15)	N1—C3—H3A	108.3
C3—N1—C1	112.51 (15)	C4—C3—H3A	108.3
C5—N1—C1	111.69 (16)	N1—C3—H3B	108.3
C3—N1—Co1	107.54 (11)	C4—C3—H3B	108.3
C5—N1—Co1	103.12 (11)	H3A—C3—H3B	107.4
C1—N1—Co1	107.83 (11)	C6—N3—H3C	120.0
C2—O2—Co1	115.18 (12)	C6—N3—H3D	120.0
C2—N2—H2A	120.0	H3C—N3—H3D	120.0
C2—N2—H2B	120.0	C4—N4—H4A	120.0
H2A—N2—H2B	120.0	C4—N4—H4B	120.0
O2—C2—N2	121.59 (17)	H4A—N4—H4B	120.0
O2—C2—C1	121.70 (17)	O4—N5—O6	120.7 (2)
N2—C2—C1	116.70 (16)	O4—N5—O5	119.5 (2)
O3—C4—N4	124.06 (18)	O6—N5—O5	119.7 (2)
O3—C4—C3	121.43 (17)	H8A—O8—H8B	108 (2)
N4—C4—C3	114.46 (18)	H7A—O7—H7B	102 (2)

O2ⁱ—Co1—O1—C6	−81.44 (15)	Co1—O2—C2—N2	169.65 (15)
O2—Co1—O1—C6	98.56 (15)	Co1—O2—C2—C1	−11.4 (2)
N1—Co1—O1—C6	16.52 (14)	C3—N1—C1—C2	−118.18 (18)
N1ⁱ—Co1—O1—C6	−163.48 (14)	C5—N1—C1—C2	112.86 (18)
O2ⁱ—Co1—N1—C3	−62.62 (13)	Co1—N1—C1—C2	0.2 (2)
O2—Co1—N1—C3	117.38 (13)	O2—C2—C1—N1	7.4 (3)
O1—Co1—N1—C3	−152.44 (13)	N2—C2—C1—N1	−173.64 (17)
O1ⁱ—Co1—N1—C3	27.56 (13)	C3—N1—C5—C6	158.56 (16)
O2ⁱ—Co1—N1—C5	57.55 (12)	C1—N1—C5—C6	−72.98 (19)
O2—Co1—N1—C5	−122.45 (12)	Co1—N1—C5—C6	42.55 (17)
O1—Co1—N1—C5	−32.27 (12)	Co1—O1—C6—N3	−175.96 (18)
O1ⁱ—Co1—N1—C5	147.73 (12)	Co1—O1—C6—C5	4.6 (2)
O2ⁱ—Co1—N1—C1	175.82 (12)	N1—C5—C6—O1	−34.3 (3)
O2—Co1—N1—C1	−4.18 (12)	N1—C5—C6—N3	146.2 (2)
O1—Co1—N1—C1	86.00 (13)	C5—N1—C3—C4	68.0 (2)
O1ⁱ—Co1—N1—C1	−94.00 (13)	C1—N1—C3—C4	−60.0 (2)
O1—Co1—O2—C2	−70.37 (14)	Co1—N1—C3—C4	−178.61 (13)
O1ⁱ—Co1—O2—C2	109.63 (14)	O3—C4—C3—N1	−25.6 (3)
N1—Co1—O2—C2	8.54 (14)	N4—C4—C3—N1	156.74 (18)
N1ⁱ—Co1—O2—C2	−171.46 (14)

Symmetry code: (i) −x+2, −y+1, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O6ⁱⁱ	0.86	2.26	3.026 (3)	149
N2—H2B···O3ⁱⁱⁱ	0.86	1.96	2.816 (2)	173
N3—H3C···O8^iv	0.86	2.11	2.958 (3)	168
N3—H3D···O5ⁱⁱⁱ	0.86	2.16	3.001 (3)	166
N4—H4A···O7^v	0.86	2.20	2.992 (3)	152
N4—H4B···O7	0.86	2.30	3.045 (3)	145
O7—H7A···O6	0.88 (2)	2.05 (2)	2.877 (3)	156 (3)
O7—H7B···O8^vi	0.87 (2)	1.96 (2)	2.826 (3)	176 (3)
O8—H8A···O1ⁱⁱ	0.85 (2)	2.14 (2)	2.976 (2)	166 (3)
O8—H8B···O6	0.85 (2)	2.16 (2)	2.980 (3)	161 (3)
O8—H8B···O5	0.85 (2)	2.42 (3)	3.078 (3)	134 (3)

Symmetry codes: (ii) −x+1, −y+1, −z+2; (iii) −x+1, −y, −z+2; (iv) x+1, y, z+1; (v) −x+1, −y, −z+1; (vi) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Co(C₆H₁₂N₄O₃)₂](NO₃)₂·4H₂O
M_r	631.41
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.4910 (17), 9.1410 (18), 9.2580 (19)
α, β, γ (°)	91.55 (3), 96.03 (3), 110.68 (3)
V (Å³)	667.0 (2)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.73
Crystal size (mm)	0.36 × 0.32 × 0.25

Data collection
Diffractometer	Siemens P4 diffractometer
Absorption correction	ψ scan (XSCANS; Siemens, 1994)
T_min, T_max	0.779, 0.838
No. of measured, independent and observed [I > 2σ(I)] reflections	3692, 2301, 2185
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.080, 1.05
No. of reflections	2301
No. of parameters	191
No. of restraints	6
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.22

Computer programs: XSCANS (Siemens, 1994), 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
N2—H2A···O6ⁱ	0.86	2.26	3.026 (3)	149
N2—H2B···O3ⁱⁱ	0.86	1.96	2.816 (2)	173
N3—H3C···O8ⁱⁱⁱ	0.86	2.11	2.958 (3)	168
N3—H3D···O5ⁱⁱ	0.86	2.16	3.001 (3)	166
N4—H4A···O7^iv	0.86	2.20	2.992 (3)	152
N4—H4B···O7	0.86	2.30	3.045 (3)	145
O7—H7A···O6	0.88 (2)	2.05 (2)	2.877 (3)	156 (3)
O7—H7B···O8^v	0.87 (2)	1.96 (2)	2.826 (3)	176 (3)
O8—H8A···O1ⁱ	0.85 (2)	2.14 (2)	2.976 (2)	166 (3)
O8—H8B···O6	0.85 (2)	2.16 (2)	2.980 (3)	161 (3)
O8—H8B···O5	0.85 (2)	2.42 (3)	3.078 (3)	134 (3)

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

Acknowledgements

This research was supported by the Huangzhou Scholar Fund (2012).

References

Kumari, N., Ward, B. D., Kar, S. & Mishra, L. (2012). Polyhedron, 33, 425–434. Web of Science CSD CrossRef CAS Google Scholar
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Siemens (1994). XSCANS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Smith, D. A., Sucheck, S., Cramer, S. & Baker, D. (1995). Synth. Commun. 25, 4123–4132. CrossRef CAS Web of Science Google Scholar