Hexaaqua­manganese(II) tetra­aqua­bis(2-amino­pyrazine-κN4)manganese(II) disulfate dihydrate

Huo, L.-H.; Gao, S.; Ng, S.W.

doi:10.1107/S1600536809045322

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page m1504

doi:10.1107/S1600536809045322

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Hexaaquamanganese(II) tetraaquabis(2-aminopyrazine-κN⁴)manganese(II) disulfate dihydrate

Li-Hua Huo,^a Shan Gao ^a and Seik Weng Ng ^b ^*

^aCollege of Chemistry and Materials Science, Heilongjiang University, Harbin 150080, People's Republic of China, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 27 October 2009; accepted 29 October 2009; online 4 November 2009)

The reaction of manganese(II) sulfate and 2-aminopyrazine affords the title salt, [Mn(H₂O)₆][Mn(C₄H₅N₃)₂(H₂O)₄](SO₄)₂·2H₂O. The metal atoms in the tetraaqua-coordinated and hexaaqua-coordinated cations lie on centers of inversion in octahedral geometries. The cations, anions and solvent water molecules are linked by O—H⋯O, N—H⋯O and O—H⋯N hydrogen bonds into a three-dimensional network.

Related literature

For the isostructural cobalt(II) analog, see: Kang et al. (2009 ).

Experimental

Crystal data

[Mn(H₂O)₆][Mn(C₄H₅N₃)₂(H₂O)₄](SO₄)₂·2H₂O
M_r = 708.43
Triclinic, $[P \overline 1]$
a = 6.6242 (3) Å
b = 8.4639 (4) Å
c = 13.2719 (8) Å
α = 75.654 (2)°
β = 78.364 (2)°
γ = 78.834 (2)°
V = 697.95 (6) Å³
Z = 1
Mo Kα radiation
μ = 1.14 mm⁻¹
T = 293 K
0.38 × 0.20 × 0.18 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.670, T_max = 0.821
6866 measured reflections
3159 independent reflections
2874 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.129
S = 1.15
3159 reflections
231 parameters
14 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.74 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1w—H1w1⋯O1	0.84 (1)	1.95 (2)	2.779 (3)	167 (4)
O1w—H1w2⋯N2ⁱ	0.85 (1)	1.94 (1)	2.792 (3)	176 (5)
O2w—H2w1⋯O3	0.85 (1)	1.95 (1)	2.775 (3)	166 (4)
O2w—H2w2⋯O1ⁱⁱ	0.85 (1)	1.92 (1)	2.770 (3)	172 (4)
O3w—H3w1⋯O2	0.85 (1)	1.90 (1)	2.744 (4)	170 (5)
O3w—H3w2⋯O6w	0.85 (1)	1.88 (1)	2.728 (4)	175 (4)
O4w—H4w1⋯O6wⁱⁱⁱ	0.85 (1)	1.96 (2)	2.780 (4)	162 (5)
O4w—H4w2⋯O2ⁱⁱⁱ	0.85 (1)	1.92 (2)	2.744 (4)	164 (5)
O5w—H5w1⋯O3^iv	0.84 (1)	2.00 (2)	2.813 (3)	159 (5)
O5w—H5w2⋯O4^v	0.85 (1)	1.88 (1)	2.726 (4)	177 (6)
O6w—H6w1⋯O3ⁱ	0.85 (1)	1.95 (2)	2.783 (3)	167 (6)
O6w—H6w2⋯O4^iv	0.85 (1)	1.87 (1)	2.709 (4)	172 (6)
N3—H3n2⋯O1^vi	0.85 (1)	2.18 (1)	3.026 (4)	172 (5)
Symmetry codes: (i) x, y-1, z; (ii) x+1, y, z; (iii) x-1, y, z; (iv) -x+1, -y+1, -z+2; (v) -x, -y+1, -z+2; (vi) -x+1, -y+3, -z+1.

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2002 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809045322/xu2658sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809045322/xu2658Isup2.hkl

checkCIF report

Related literature top

For the isostructural cobalt(II) analog, see: Kang et al. (2009).

Experimental top

To an aqueous solution of 3-aminopyrazine (0.19 g, 2 mmol) was added manganese(II) sulfate tetrahydrate (0.45 g, 2 mmol). Colorless crystals of the salt separated from the solution after a few days. CH&N elemental analysis. Calc. for C₈H₃₄N₆O₂₀S₂Mn₂: C 13.56, H 4.84, N 11.86%; found: C 13.52, H 4.80, N 11.85%.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalClear (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of [Mn(H₂O)₆] [Mn(H₂O)₄(C₄H₅N₃)₂] 2[SO₄]^.2H₂O at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Hexaaquamanganese(II) tetraaquabis(2-aminopyrazine-κN⁴)manganese(II) disulfate dihydrate top

Crystal data top

[Mn(H₂O)₆][Mn(C₄H₅N₃)₂(H₂O)₄](SO₄)₂·2H₂O	Z = 1
M_r = 708.43	F(000) = 366
Triclinic, P1	D_x = 1.685 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.6242 (3) Å	Cell parameters from 6492 reflections
b = 8.4639 (4) Å	θ = 3.2–27.5°
c = 13.2719 (8) Å	µ = 1.14 mm⁻¹
α = 75.654 (2)°	T = 293 K
β = 78.364 (2)°	Prism, colorless
γ = 78.834 (2)°	0.38 × 0.20 × 0.18 mm
V = 697.95 (6) Å³

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	3159 independent reflections
Radiation source: fine-focus sealed tube	2874 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ω scans	θ_max = 27.5°, θ_min = 3.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −8→8
T_min = 0.670, T_max = 0.821	k = −10→10
6866 measured reflections	l = −17→17

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.129	H atoms treated by a mixture of independent and constrained refinement
S = 1.15	w = 1/[σ²(F_o²) + (0.0556P)² + 1.1503P] where P = (F_o² + 2F_c²)/3
3159 reflections	(Δ/σ)_max = 0.001
231 parameters	Δρ_max = 0.74 e Å⁻³
14 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

[Mn(H₂O)₆][Mn(C₄H₅N₃)₂(H₂O)₄](SO₄)₂·2H₂O	γ = 78.834 (2)°
M_r = 708.43	V = 697.95 (6) Å³
Triclinic, P1	Z = 1
a = 6.6242 (3) Å	Mo Kα radiation
b = 8.4639 (4) Å	µ = 1.14 mm⁻¹
c = 13.2719 (8) Å	T = 293 K
α = 75.654 (2)°	0.38 × 0.20 × 0.18 mm
β = 78.364 (2)°

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	3159 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	2874 reflections with I > 2σ(I)
T_min = 0.670, T_max = 0.821	R_int = 0.025
6866 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	14 restraints
wR(F²) = 0.129	H atoms treated by a mixture of independent and constrained refinement
S = 1.15	Δρ_max = 0.74 e Å⁻³
3159 reflections	Δρ_min = −0.40 e Å⁻³
231 parameters

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

	x	y	z	U_iso*/U_eq
Mn1	1.0000	1.0000	0.5000	0.02349 (17)
Mn2	0.0000	0.5000	1.0000	0.02867 (18)
S1	0.47994 (10)	0.88750 (9)	0.80279 (5)	0.02457 (18)
O1	0.4091 (3)	0.9828 (3)	0.70435 (17)	0.0322 (5)
O2	0.5386 (4)	0.7129 (3)	0.7978 (2)	0.0444 (6)
O3	0.6644 (3)	0.9501 (3)	0.81657 (17)	0.0318 (5)
O4	0.3121 (4)	0.9084 (4)	0.89137 (19)	0.0441 (6)
O1W	0.7084 (4)	0.9110 (3)	0.53580 (19)	0.0335 (5)
O2W	1.0209 (4)	0.9617 (3)	0.66525 (17)	0.0345 (5)
O3W	0.2937 (4)	0.4732 (3)	0.8939 (2)	0.0471 (7)
O4W	−0.1480 (4)	0.4748 (3)	0.8707 (2)	0.0429 (6)
O5W	0.0400 (4)	0.2353 (3)	1.0577 (2)	0.0456 (6)
O6W	0.6189 (4)	0.2200 (3)	0.9081 (2)	0.0399 (6)
N1	0.8363 (4)	1.2689 (3)	0.4980 (2)	0.0301 (5)
N2	0.7098 (4)	1.6040 (3)	0.4930 (2)	0.0344 (6)
N3	0.7810 (6)	1.6587 (4)	0.3104 (3)	0.0482 (8)
C1	0.8414 (5)	1.3800 (4)	0.4078 (3)	0.0334 (7)
H1	0.8899	1.3447	0.3450	0.040*
C2	0.7760 (5)	1.5496 (4)	0.4039 (3)	0.0325 (6)
C3	0.7019 (5)	1.4892 (4)	0.5836 (3)	0.0376 (7)
H3	0.6532	1.5237	0.6466	0.045*
C4	0.7623 (5)	1.3238 (4)	0.5874 (3)	0.0348 (7)
H4	0.7522	1.2491	0.6521	0.042*
H1W1	0.614 (5)	0.948 (5)	0.581 (3)	0.048 (12)*
H1W2	0.715 (7)	0.817 (3)	0.521 (4)	0.053 (13)*
H2W1	0.919 (4)	0.972 (5)	0.714 (2)	0.028 (9)*
H2W2	1.135 (4)	0.967 (5)	0.683 (3)	0.044 (11)*
H3W1	0.357 (7)	0.556 (4)	0.866 (4)	0.066 (15)*
H3W2	0.391 (5)	0.392 (3)	0.901 (3)	0.039 (11)*
H4W1	−0.195 (8)	0.386 (4)	0.876 (4)	0.073 (17)*
H4W2	−0.247 (5)	0.554 (4)	0.859 (4)	0.063 (15)*
H5W1	0.126 (6)	0.160 (4)	1.089 (3)	0.059 (14)*
H5W2	−0.072 (5)	0.194 (7)	1.074 (5)	0.081 (18)*
H6W1	0.624 (9)	0.148 (5)	0.873 (4)	0.079 (18)*
H6W2	0.641 (9)	0.170 (6)	0.9698 (19)	0.072 (17)*
H3N1	0.831 (7)	1.629 (6)	0.252 (2)	0.062 (15)*
H3N2	0.738 (8)	1.7613 (19)	0.308 (4)	0.060 (14)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.0217 (3)	0.0225 (3)	0.0255 (3)	−0.0022 (2)	−0.0054 (2)	−0.0034 (2)
Mn2	0.0218 (3)	0.0271 (3)	0.0341 (3)	−0.0032 (2)	−0.0067 (2)	0.0002 (2)
S1	0.0209 (3)	0.0257 (3)	0.0260 (3)	−0.0046 (3)	−0.0066 (2)	−0.0004 (3)
O1	0.0289 (11)	0.0353 (12)	0.0302 (11)	−0.0007 (9)	−0.0115 (9)	−0.0009 (9)
O2	0.0423 (14)	0.0252 (11)	0.0645 (17)	−0.0035 (10)	−0.0175 (12)	−0.0014 (11)
O3	0.0224 (10)	0.0385 (12)	0.0356 (11)	−0.0062 (9)	−0.0079 (8)	−0.0062 (9)
O4	0.0313 (12)	0.0672 (17)	0.0317 (12)	−0.0132 (12)	0.0012 (10)	−0.0078 (11)
O1W	0.0277 (11)	0.0325 (12)	0.0423 (13)	−0.0092 (9)	0.0038 (9)	−0.0157 (10)
O2W	0.0258 (11)	0.0521 (14)	0.0264 (10)	−0.0058 (10)	−0.0080 (9)	−0.0068 (10)
O3W	0.0281 (12)	0.0356 (14)	0.0671 (18)	−0.0064 (11)	0.0055 (12)	−0.0012 (12)
O4W	0.0395 (14)	0.0380 (14)	0.0542 (15)	−0.0039 (11)	−0.0212 (12)	−0.0059 (12)
O5W	0.0318 (13)	0.0320 (12)	0.0679 (17)	−0.0074 (10)	−0.0194 (12)	0.0096 (12)
O6W	0.0477 (14)	0.0317 (12)	0.0413 (14)	−0.0016 (11)	−0.0131 (11)	−0.0086 (10)
N1	0.0269 (12)	0.0226 (12)	0.0390 (14)	−0.0011 (10)	−0.0063 (10)	−0.0044 (10)
N2	0.0293 (13)	0.0255 (12)	0.0498 (16)	−0.0013 (10)	−0.0095 (12)	−0.0109 (11)
N3	0.063 (2)	0.0285 (15)	0.0451 (18)	0.0031 (15)	−0.0061 (16)	−0.0039 (13)
C1	0.0347 (16)	0.0256 (15)	0.0380 (16)	0.0001 (12)	−0.0061 (13)	−0.0069 (12)
C2	0.0289 (15)	0.0238 (14)	0.0435 (17)	−0.0014 (12)	−0.0071 (13)	−0.0060 (12)
C3	0.0337 (16)	0.0391 (18)	0.0425 (18)	0.0019 (14)	−0.0073 (14)	−0.0182 (14)
C4	0.0318 (16)	0.0335 (16)	0.0352 (16)	0.0037 (13)	−0.0075 (13)	−0.0051 (13)

Geometric parameters (Å, º) top

Mn1—O1W	2.131 (2)	O3W—H3W1	0.849 (10)
Mn1—O1Wⁱ	2.131 (2)	O3W—H3W2	0.849 (10)
Mn1—O2Wⁱ	2.165 (2)	O4W—H4W1	0.848 (10)
Mn1—O2W	2.165 (2)	O4W—H4W2	0.850 (10)
Mn1—N1	2.320 (2)	O5W—H5W1	0.849 (10)
Mn1—N1ⁱ	2.320 (2)	O5W—H5W2	0.850 (10)
Mn2—O3W	2.168 (3)	O6W—H6W1	0.850 (10)
Mn2—O3Wⁱⁱ	2.168 (3)	O6W—H6W2	0.850 (10)
Mn2—O4W	2.212 (3)	N1—C1	1.325 (4)
Mn2—O4Wⁱⁱ	2.212 (3)	N1—C4	1.347 (4)
Mn2—O5Wⁱⁱ	2.163 (2)	N2—C2	1.337 (4)
Mn2—O5W	2.163 (2)	N2—C3	1.344 (5)
S1—O4	1.466 (2)	N3—C2	1.350 (5)
S1—O2	1.468 (3)	N3—H3N1	0.855 (10)
S1—O1	1.468 (2)	N3—H3N2	0.854 (10)
S1—O3	1.482 (2)	C1—C2	1.408 (4)
O1W—H1W1	0.844 (10)	C1—H1	0.9300
O1W—H1W2	0.851 (10)	C3—C4	1.371 (5)
O2W—H2W1	0.846 (10)	C3—H3	0.9300
O2W—H2W2	0.852 (10)	C4—H4	0.9300

O1W—Mn1—O1Wⁱ	180.000 (1)	Mn1—O1W—H1W1	118 (3)
O1W—Mn1—O2Wⁱ	87.90 (9)	Mn1—O1W—H1W2	114 (3)
O1Wⁱ—Mn1—O2Wⁱ	92.10 (9)	H1W1—O1W—H1W2	123 (4)
O1W—Mn1—O2W	92.10 (9)	Mn1—O2W—H2W1	125 (3)
O1Wⁱ—Mn1—O2W	87.90 (9)	Mn1—O2W—H2W2	120 (3)
O2Wⁱ—Mn1—O2W	180.000 (1)	H2W1—O2W—H2W2	112 (4)
O1W—Mn1—N1	91.71 (9)	Mn2—O3W—H3W1	120 (4)
O1Wⁱ—Mn1—N1	88.29 (9)	Mn2—O3W—H3W2	126 (3)
O2Wⁱ—Mn1—N1	89.32 (10)	H3W1—O3W—H3W2	104 (4)
O2W—Mn1—N1	90.68 (10)	Mn2—O4W—H4W1	119 (4)
O1W—Mn1—N1ⁱ	88.29 (9)	Mn2—O4W—H4W2	110 (3)
O1Wⁱ—Mn1—N1ⁱ	91.71 (9)	H4W1—O4W—H4W2	107 (5)
O2Wⁱ—Mn1—N1ⁱ	90.68 (10)	Mn2—O5W—H5W1	139 (3)
O2W—Mn1—N1ⁱ	89.32 (10)	Mn2—O5W—H5W2	115 (4)
N1—Mn1—N1ⁱ	180.000 (1)	H5W1—O5W—H5W2	103 (5)
O5Wⁱⁱ—Mn2—O5W	180.000 (1)	H6W1—O6W—H6W2	108 (5)
O5Wⁱⁱ—Mn2—O3W	90.64 (10)	C1—N1—C4	117.4 (3)
O5W—Mn2—O3W	89.36 (10)	C1—N1—Mn1	119.9 (2)
O5Wⁱⁱ—Mn2—O3Wⁱⁱ	89.36 (10)	C4—N1—Mn1	121.9 (2)
O5W—Mn2—O3Wⁱⁱ	90.64 (10)	C2—N2—C3	116.8 (3)
O3W—Mn2—O3Wⁱⁱ	180.000 (1)	C2—N3—H3N1	122 (3)
O5Wⁱⁱ—Mn2—O4W	89.84 (10)	C2—N3—H3N2	121 (3)
O5W—Mn2—O4W	90.16 (10)	H3N1—N3—H3N2	117 (5)
O3W—Mn2—O4W	86.45 (11)	N1—C1—C2	122.2 (3)
O3Wⁱⁱ—Mn2—O4W	93.55 (11)	N1—C1—H1	118.9
O5Wⁱⁱ—Mn2—O4Wⁱⁱ	90.16 (10)	C2—C1—H1	118.9
O5W—Mn2—O4Wⁱⁱ	89.84 (10)	N2—C2—N3	119.4 (3)
O3W—Mn2—O4Wⁱⁱ	93.55 (11)	N2—C2—C1	120.2 (3)
O3Wⁱⁱ—Mn2—O4Wⁱⁱ	86.45 (11)	N3—C2—C1	120.4 (3)
O4W—Mn2—O4Wⁱⁱ	180.000 (1)	N2—C3—C4	123.1 (3)
O4—S1—O2	110.85 (17)	N2—C3—H3	118.4
O4—S1—O1	109.03 (14)	C4—C3—H3	118.4
O2—S1—O1	109.60 (15)	N1—C4—C3	120.3 (3)
O4—S1—O3	109.10 (14)	N1—C4—H4	119.9
O2—S1—O3	109.02 (14)	C3—C4—H4	119.9
O1—S1—O3	109.22 (13)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1w1···O1	0.84 (1)	1.95 (2)	2.779 (3)	167 (4)
O1w—H1w2···N2ⁱⁱⁱ	0.85 (1)	1.94 (1)	2.792 (3)	176 (5)
O2w—H2w1···O3	0.85 (1)	1.95 (1)	2.775 (3)	166 (4)
O2w—H2w2···O1^iv	0.85 (1)	1.92 (1)	2.770 (3)	172 (4)
O3w—H3w1···O2	0.85 (1)	1.90 (1)	2.744 (4)	170 (5)
O3w—H3w2···O6w	0.85 (1)	1.88 (1)	2.728 (4)	175 (4)
O4w—H4w1···O6w^v	0.85 (1)	1.96 (2)	2.780 (4)	162 (5)
O4w—H4w2···O2^v	0.85 (1)	1.92 (2)	2.744 (4)	164 (5)
O5w—H5w1···O3^vi	0.84 (1)	2.00 (2)	2.813 (3)	159 (5)
O5w—H5w2···O4ⁱⁱ	0.85 (1)	1.88 (1)	2.726 (4)	177 (6)
O6w—H6w1···O3ⁱⁱⁱ	0.85 (1)	1.95 (2)	2.783 (3)	167 (6)
O6w—H6w2···O4^vi	0.85 (1)	1.87 (1)	2.709 (4)	172 (6)
N3—H3n2···O1^vii	0.85 (1)	2.18 (1)	3.026 (4)	172 (5)

Symmetry codes: (ii) −x, −y+1, −z+2; (iii) x, y−1, z; (iv) x+1, y, z; (v) x−1, y, z; (vi) −x+1, −y+1, −z+2; (vii) −x+1, −y+3, −z+1.

Experimental details

Crystal data
Chemical formula	[Mn(H₂O)₆][Mn(C₄H₅N₃)₂(H₂O)₄](SO₄)₂·2H₂O
M_r	708.43
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	6.6242 (3), 8.4639 (4), 13.2719 (8)
α, β, γ (°)	75.654 (2), 78.364 (2), 78.834 (2)
V (Å³)	697.95 (6)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	1.14
Crystal size (mm)	0.38 × 0.20 × 0.18

Data collection
Diffractometer	Rigaku R-AXIS RAPID IP diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.670, 0.821
No. of measured, independent and observed [I > 2σ(I)] reflections	6866, 3159, 2874
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.129, 1.15
No. of reflections	3159
No. of parameters	231
No. of restraints	14
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.74, −0.40

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalClear (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1w1···O1	0.84 (1)	1.95 (2)	2.779 (3)	167 (4)
O1w—H1w2···N2ⁱ	0.85 (1)	1.94 (1)	2.792 (3)	176 (5)
O2w—H2w1···O3	0.85 (1)	1.95 (1)	2.775 (3)	166 (4)
O2w—H2w2···O1ⁱⁱ	0.85 (1)	1.92 (1)	2.770 (3)	172 (4)
O3w—H3w1···O2	0.85 (1)	1.90 (1)	2.744 (4)	170 (5)
O3w—H3w2···O6w	0.85 (1)	1.88 (1)	2.728 (4)	175 (4)
O4w—H4w1···O6wⁱⁱⁱ	0.85 (1)	1.96 (2)	2.780 (4)	162 (5)
O4w—H4w2···O2ⁱⁱⁱ	0.85 (1)	1.92 (2)	2.744 (4)	164 (5)
O5w—H5w1···O3^iv	0.84 (1)	2.00 (2)	2.813 (3)	159 (5)
O5w—H5w2···O4^v	0.85 (1)	1.88 (1)	2.726 (4)	177 (6)
O6w—H6w1···O3ⁱ	0.85 (1)	1.95 (2)	2.783 (3)	167 (6)
O6w—H6w2···O4^iv	0.85 (1)	1.87 (1)	2.709 (4)	172 (6)
N3—H3n2···O1^vi	0.85 (1)	2.18 (1)	3.026 (4)	172 (5)

Symmetry codes: (i) x, y−1, z; (ii) x+1, y, z; (iii) x−1, y, z; (iv) −x+1, −y+1, −z+2; (v) −x, −y+1, −z+2; (vi) −x+1, −y+3, −z+1.

Acknowledgements

We thank the Natural Science Foundation of Heilongjiang Province (No. B200501), Heilongjiang University, China, and the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Kang, W., Huo, L.-H., Gao, S. & Ng, S. W. (2009). Acta Cryst. E65, m1503. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2002). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar

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