μ-4,4′-Diazenediyldiphthalato-κ2O2:O2′-bis­[penta­aqua­manganese(II)] tetra­hydrate

Bai, J.-W.; Wang, J.; Hou, Y.; Zhao, B.-Z.; Fu, Q.

doi:10.1107/S1600536807061314

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 1| January 2008| Pages m3-m4

https://doi.org/10.1107/S1600536807061314

Open

access

μ-4,4′-Diazenediyldiphthalato-κ²O²:O^2′-bis[pentaaquamanganese(II)] tetrahydrate

Jian-Wei Bai,^a Jun Wang,^a,^b Yang Hou,^a Bao-Zhong Zhao ^a ^* and Qiang Fu ^a

^aCollege of Chemistry, Northeast Normal University, Changchun 130024, People's Republic of China, and ^bDepartment of Chemistry, SiChuan University of Science & Engineering, Zigong 643000, People's Republic of China
^*Correspondence e-mail: lulusczg@126.com

(Received 13 November 2007; accepted 20 November 2007; online 6 December 2007)

The dinuclear complex in the title compound, [Mn₂(C₁₆H₆N₂O₈)(H₂O)₁₀]·4H₂O, lies on an inversion center. Two delocalized carboxylate groups are each connected in a monodentate fashion to two similar pentaaquamanganese units, whereas the other two localized carboxylate groups are uncoordinated. The metal ion has octahedral coordination, with the O atom of a carboxylate group and three coordinated water molecules forming the equatorial plane [Mn—O_COO = 2.143 (4) Å] and two water molecules occupying the axial positions. The architecture is further consolidated by extensive hydrogen bonds for which coordinated water molecules serve as donors or acceptors.

Related literature

For related literature, see: Gokel et al. (2004 ); Lassahn et al. (2004 ); Liu & Xu (2005 ); Shan et al. (2001 ); Wang et al. (2007 ).

Experimental

Crystal data

[Mn₂(C₁₆H₆N₂O₈)(H₂O)₁₀]·4H₂O
M_r = 716.33
Monoclinic, P 2₁ /c
a = 6.9674 (10) Å
b = 15.186 (2) Å
c = 13.5576 (19) Å
β = 98.812 (2)°
V = 1417.5 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.99 mm⁻¹
T = 298 (2) K
0.29 × 0.25 × 0.18 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.763, T_max = 0.842
7535 measured reflections
2649 independent reflections
2349 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.090
S = 1.06
2649 reflections
184 parameters
H-atom parameters constrained
Δρ_max = 0.64 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O7W	0.82	1.95	2.760 (3)	170
O1W—H1WB⋯O4	0.82	1.85	2.675 (2)	176
O2W—H2WA⋯O4Wⁱ	0.81	2.16	2.948 (2)	163
O2W—H2WA⋯O1ⁱ	0.81	2.64	3.061 (2)	114
O2W—H2WB⋯O1Wⁱⁱ	0.80	2.63	3.293 (3)	142
O3W—H3WB⋯O6W	0.83	2.00	2.818 (2)	171
O3W—H3WA⋯O3ⁱⁱⁱ	0.81	1.89	2.696 (2)	172
O4W—H4WA⋯O2ⁱ	0.81	2.00	2.8162 (19)	174
O4W—H4WB⋯O3^iv	0.82	1.94	2.758 (2)	178
O5W—H5WA⋯O2^iv	0.82	1.95	2.759 (2)	169
O5W—H5WB⋯O7W^v	0.82	1.93	2.744 (2)	173
O6W—H6WA⋯O4ⁱⁱ	0.87	1.81	2.677 (2)	174
O6W—H6WB⋯O2ⁱ	0.87	2.03	2.894 (2)	175
O7W—H7WB⋯N1^vi	0.91	1.96	2.859 (3)	174
O7W—H7WA⋯O6W^vii	0.87	1.92	2.780 (3)	169
Symmetry codes: (i) -x+2, -y+1, -z+2; (ii) -x+3, -y+1, -z+2; (iii) $[-x+3, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iv) $[-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (v) x-1, y, z; (vi) -x+2, -y+1, -z+1; (vii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ) and ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536807061314/dn2281sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807061314/dn2281Isup2.hkl

checkCIF report

Comment top

Transition metal complexes with bipyridine derivatives are suitable models for the study of excited state dynamics. In addition, they are of interest for the development of light-energy conversion devices and optical sensors (Gokel et al., 2004; Shan et al., 2001; Lassahn et al., 2004). Although a great number of metal carboxylate have been obtained to date, the rational design and synthesis of novel metal carboxylates by employing new synthetic tools or by varying the natures of the reactants and synthetic conditions are currently under active investigation (Liu & Xu, 2005). In this context, L ligand which can exhibit a variety of coordination abilities and has a tendency to form architectures with multi-dimensional frameworks (Wang et al., 2007). In this paper, we report the synthesis and crystal structure of the title complex,(I).

The title complex (I) is arranged around a crystallographic inversion center located in the middle of the N=N bond. The metal ion is octahedrally coordinated by the oxygen atom of the carboxylate group [Mn-Ocarboxylate =2.143 (4)° A]and five coordinated water molecules. Two delocalized carboxyl –CO₂ groups are each connected via monodentate fashion to two similar pentaaquamanganese units whereas the other two localized carboxyl –CO₂ are free. The architecture is further consolidated by extensive hydrogen bonds for which the water molecules serves as donors or acceptors (Table 1).

Related literature top

For related literature, see: Gokel et al. (2004); Lassahn et al. (2004); Liu & Xu (2005); Shan et al. (2001); Wang et al. (2007).

Experimental top

MnSO4(0.032 g, 0.017 mmol), L(0.029 g, 0.014 mmol) and NaOH(0.048 mmol,0.12 mmol), were added in a mixed solvent of acetonitrile, the mixture was heated for six hours under reflux. During the process stirring and influx were required. The resultant was then filtered to give a pure solution which was infiltrated by diethyl ether freely in a closed vessel, a weeks later some single crystals of the size suitable for X-Ray diffraction analysis.

Structure description top

For related literature, see: Gokel et al. (2004); Lassahn et al. (2004); Liu & Xu (2005); Shan et al. (2001); Wang et al. (2007).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Figures top

Fig. 1. View of complex (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. Hydrogen bonds are shown as dashed lines. H atoms are represented as small spheres of arbitrary radii. [Symmetry code (i): 1 - x,1 - y,1 - z].

µ-4,4'-Diazenediyldiphthalato-κ²O²:O^2'– bis[pentaaquamanganese(II)] tetrahydrate top

Crystal data top

[Mn₂(C₁₆H₆N₂O₈)(H₂O)₁₀]·4H₂O	F(000) = 740
M_r = 716.33	D_x = 1.678 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2649 reflections
a = 6.9674 (10) Å	θ = 2.0–25.5°
b = 15.186 (2) Å	µ = 0.99 mm⁻¹
c = 13.5576 (19) Å	T = 298 K
β = 98.812 (2)°	Block, yellow
V = 1417.5 (3) Å³	0.29 × 0.25 × 0.18 mm
Z = 2

Data collection top

Bruker APEX-II area-detector diffractometer	2649 independent reflections
Radiation source: fine-focus sealed tube	2349 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
φ and ω scan	θ_max = 25.5°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −8→7
T_min = 0.763, T_max = 0.842	k = −18→17
7535 measured reflections	l = −16→16

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.090	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0505P)² + 0.4924P] where P = (F_o² + 2F_c²)/3
2649 reflections	(Δ/σ)_max = 0.001
184 parameters	Δρ_max = 0.64 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

[Mn₂(C₁₆H₆N₂O₈)(H₂O)₁₀]·4H₂O	V = 1417.5 (3) Å³
M_r = 716.33	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.9674 (10) Å	µ = 0.99 mm⁻¹
b = 15.186 (2) Å	T = 298 K
c = 13.5576 (19) Å	0.29 × 0.25 × 0.18 mm
β = 98.812 (2)°

Data collection top

Bruker APEX-II area-detector diffractometer	2649 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	2349 reflections with I > 2σ(I)
T_min = 0.763, T_max = 0.842	R_int = 0.019
7535 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.090	H-atom parameters constrained
S = 1.06	Δρ_max = 0.64 e Å⁻³
2649 reflections	Δρ_min = −0.30 e Å⁻³
184 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
Mn1	1.15210 (4)	0.59508 (2)	0.87665 (2)	0.02864 (12)
O1	0.9887 (2)	0.47791 (9)	0.83401 (10)	0.0337 (3)
O2	0.9981 (2)	0.33199 (9)	0.83063 (10)	0.0333 (3)
O3	1.3292 (2)	0.26635 (10)	0.62459 (11)	0.0367 (4)
O4	1.3672 (2)	0.37832 (10)	0.73190 (12)	0.0388 (4)
O1W	1.3818 (3)	0.54312 (11)	0.80243 (14)	0.0528 (5)
H1WA	1.4600	0.5680	0.7730	0.079*
H1WB	1.3730	0.4930	0.7790	0.079*
O2W	1.2906 (2)	0.52547 (12)	1.01240 (12)	0.0484 (4)
H2WA	1.2359	0.4830	1.0320	0.073*
H2WB	1.3829	0.5350	1.0540	0.073*
O3W	1.3327 (2)	0.70714 (11)	0.92397 (13)	0.0479 (4)
H3WB	1.3530	0.7149	0.9850	0.072*
H3WA	1.4280	0.7279	0.9050	0.072*
O4W	0.9230 (2)	0.63843 (10)	0.96205 (10)	0.033
H4WA	0.9370	0.6470	1.0220	0.050*
H4WB	0.8500	0.6770	0.9370	0.050*
O5W	0.9978 (2)	0.66502 (10)	0.74917 (10)	0.0379 (4)
H5WA	1.0061	0.7170	0.7330	0.057*
H5WB	0.8841	0.6530	0.7280	0.057*
O6W	1.3892 (3)	0.71325 (14)	1.13418 (13)	0.0563 (5)
H6WA	1.4620	0.6809	1.1780	0.085*
H6WB	1.2720	0.7029	1.1450	0.085*
O7W	1.6084 (3)	0.63676 (12)	0.68914 (14)	0.0547 (5)
H7WB	1.5680	0.6040	0.6340	0.082*
H7WA	1.5380	0.6840	0.6800	0.082*
N1	0.5413 (2)	0.47199 (12)	0.47708 (12)	0.0319 (4)
C1	0.9867 (3)	0.40586 (12)	0.78879 (14)	0.0235 (4)
C2	0.9492 (3)	0.40791 (12)	0.67589 (14)	0.0225 (4)
C4	1.2725 (3)	0.33562 (13)	0.66100 (14)	0.0266 (4)
C7	0.7227 (3)	0.44018 (14)	0.52778 (14)	0.0275 (4)
C6	0.8475 (3)	0.40308 (13)	0.46864 (15)	0.0299 (5)
H6	0.8129	0.4012	0.3996	0.036*
C5	1.0234 (3)	0.36904 (13)	0.51324 (14)	0.0284 (4)
H5	1.1074	0.3444	0.4737	0.034*
C3	1.0769 (3)	0.37103 (13)	0.61650 (14)	0.0240 (4)
C8	0.7726 (3)	0.44200 (13)	0.63154 (14)	0.0259 (4)
H8	0.6874	0.4661	0.6707	0.031*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.0314 (2)	0.02601 (19)	0.02938 (19)	−0.00248 (12)	0.00726 (14)	−0.00193 (12)
O1	0.0456 (9)	0.0266 (8)	0.0288 (7)	−0.0029 (6)	0.0055 (6)	−0.0064 (6)
O2	0.0488 (9)	0.0263 (8)	0.0237 (7)	0.0037 (6)	0.0023 (6)	0.0022 (6)
O3	0.0288 (8)	0.0391 (9)	0.0409 (9)	0.0106 (6)	0.0014 (7)	−0.0095 (7)
O4	0.0311 (8)	0.0381 (9)	0.0432 (9)	0.0052 (7)	−0.0073 (7)	−0.0100 (7)
O1W	0.0564 (11)	0.0408 (10)	0.0688 (12)	−0.0066 (8)	0.0341 (9)	−0.0147 (8)
O2W	0.0398 (9)	0.0596 (11)	0.0423 (9)	−0.0040 (8)	−0.0046 (7)	0.0144 (8)
O3W	0.0429 (10)	0.0472 (10)	0.0571 (11)	−0.0201 (8)	0.0179 (8)	−0.0139 (8)
O4W	0.039	0.036	0.025	0.007	0.005	0.002
O5W	0.0456 (9)	0.0326 (8)	0.0347 (8)	−0.0026 (7)	0.0037 (7)	0.0072 (7)
O6W	0.0440 (10)	0.0748 (13)	0.0481 (10)	0.0035 (9)	0.0002 (8)	0.0117 (9)
O7W	0.0524 (11)	0.0463 (11)	0.0631 (12)	−0.0002 (8)	0.0013 (9)	−0.0084 (9)
N1	0.0277 (9)	0.0406 (10)	0.0261 (8)	0.0068 (7)	−0.0006 (7)	0.0023 (7)
C1	0.0198 (9)	0.0282 (11)	0.0222 (9)	−0.0003 (7)	0.0024 (8)	−0.0009 (8)
C2	0.0238 (10)	0.0211 (9)	0.0220 (9)	0.0001 (7)	0.0019 (7)	0.0007 (7)
C4	0.0232 (10)	0.0298 (11)	0.0272 (10)	0.0027 (8)	0.0051 (8)	0.0024 (8)
C7	0.0243 (10)	0.0309 (11)	0.0256 (10)	0.0041 (8)	−0.0010 (8)	0.0030 (8)
C6	0.0320 (11)	0.0356 (12)	0.0211 (9)	0.0039 (9)	0.0008 (8)	0.0007 (8)
C5	0.0287 (11)	0.0336 (11)	0.0237 (10)	0.0043 (9)	0.0065 (8)	−0.0023 (8)
C3	0.0236 (10)	0.0219 (10)	0.0262 (10)	0.0022 (7)	0.0033 (8)	0.0017 (8)
C8	0.0243 (10)	0.0282 (10)	0.0258 (9)	0.0057 (8)	0.0055 (8)	0.0005 (8)

Geometric parameters (Å, º) top

Mn1—O1	2.1435 (15)	O5W—H5WB	0.8207
Mn1—O3W	2.1548 (16)	O6W—H6WA	0.8708
Mn1—O1W	2.1657 (17)	O6W—H6WB	0.8656
Mn1—O5W	2.1683 (15)	O7W—H7WB	0.9061
Mn1—O4W	2.2108 (14)	O7W—H7WA	0.8666
Mn1—O2W	2.2119 (16)	N1—N1ⁱ	1.245 (3)
O1—C1	1.253 (2)	N1—C7	1.427 (3)
O2—C1	1.254 (2)	C1—C2	1.513 (3)
O3—C4	1.251 (2)	C2—C8	1.385 (3)
O4—C4	1.259 (2)	C2—C3	1.405 (3)
O1W—H1WA	0.8156	C4—C3	1.503 (3)
O1W—H1WB	0.8230	C7—C6	1.389 (3)
O2W—H2WA	0.8145	C7—C8	1.397 (3)
O2W—H2WB	0.8008	C6—C5	1.382 (3)
O3W—H3WB	0.8259	C6—H6	0.9300
O3W—H3WA	0.8120	C5—C3	1.393 (3)
O4W—H4WA	0.8148	C5—H5	0.9300
O4W—H4WB	0.8151	C8—H8	0.9300
O5W—H5WA	0.8240

O1—Mn1—O3W	176.04 (7)	Mn1—O5W—H5WB	120.3
O1—Mn1—O1W	88.39 (6)	H5WA—O5W—H5WB	102.9
O3W—Mn1—O1W	89.24 (7)	H6WA—O6W—H6WB	104.4
O1—Mn1—O5W	90.78 (6)	H7WB—O7W—H7WA	103.9
O3W—Mn1—O5W	92.65 (7)	N1ⁱ—N1—C7	115.7 (2)
O1W—Mn1—O5W	96.88 (7)	O1—C1—O2	124.37 (18)
O1—Mn1—O4W	89.55 (6)	O1—C1—C2	117.65 (16)
O3W—Mn1—O4W	92.55 (6)	O2—C1—C2	117.72 (16)
O1W—Mn1—O4W	174.90 (6)	C8—C2—C3	119.93 (17)
O5W—Mn1—O4W	87.82 (6)	C8—C2—C1	116.82 (17)
O1—Mn1—O2W	88.49 (6)	C3—C2—C1	123.04 (17)
O3W—Mn1—O2W	88.24 (7)	O3—C4—O4	125.04 (18)
O1W—Mn1—O2W	87.31 (7)	O3—C4—C3	117.63 (17)
O5W—Mn1—O2W	175.73 (6)	O4—C4—C3	117.32 (18)
O4W—Mn1—O2W	87.97 (6)	C6—C7—C8	120.53 (18)
C1—O1—Mn1	145.33 (14)	C6—C7—N1	116.47 (17)
Mn1—O1W—H1WA	130.9	C8—C7—N1	122.95 (17)
Mn1—O1W—H1WB	120.0	C5—C6—C7	119.41 (18)
H1WA—O1W—H1WB	104.8	C5—C6—H6	120.3
Mn1—O2W—H2WA	118.9	C7—C6—H6	120.3
Mn1—O2W—H2WB	134.5	C6—C5—C3	120.97 (18)
H2WA—O2W—H2WB	106.2	C6—C5—H5	119.5
Mn1—O3W—H3WB	114.5	C3—C5—H5	119.5
Mn1—O3W—H3WA	132.9	C5—C3—C2	119.30 (18)
H3WB—O3W—H3WA	103.8	C5—C3—C4	118.84 (17)
Mn1—O4W—H4WA	125.8	C2—C3—C4	121.84 (17)
Mn1—O4W—H4WB	116.8	C2—C8—C7	119.84 (18)
H4WA—O4W—H4WB	105.8	C2—C8—H8	120.1
Mn1—O5W—H5WA	129.4	C7—C8—H8	120.1

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O7W	0.82	1.95	2.760 (3)	170
O1W—H1WB···O4	0.82	1.85	2.675 (2)	176
O2W—H2WA···O4Wⁱⁱ	0.81	2.16	2.948 (2)	163
O2W—H2WA···O1ⁱⁱ	0.81	2.64	3.061 (2)	114
O2W—H2WB···O1Wⁱⁱⁱ	0.80	2.63	3.293 (3)	142
O3W—H3WB···O6W	0.83	2.00	2.818 (2)	171
O3W—H3WA···O3^iv	0.81	1.89	2.696 (2)	172
O4W—H4WA···O2ⁱⁱ	0.81	2.00	2.8162 (19)	174
O4W—H4WB···O3^v	0.82	1.94	2.758 (2)	178
O5W—H5WA···O2^v	0.82	1.95	2.759 (2)	169
O5W—H5WB···O7W^vi	0.82	1.93	2.744 (2)	173
O6W—H6WA···O4ⁱⁱⁱ	0.87	1.81	2.677 (2)	174
O6W—H6WB···O2ⁱⁱ	0.87	2.03	2.894 (2)	175
O7W—H7WB···N1^vii	0.91	1.96	2.859 (3)	174
O7W—H7WA···O6W^viii	0.87	1.92	2.780 (3)	169

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

Experimental details

Crystal data
Chemical formula	[Mn₂(C₁₆H₆N₂O₈)(H₂O)₁₀]·4H₂O
M_r	716.33
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	6.9674 (10), 15.186 (2), 13.5576 (19)
β (°)	98.812 (2)
V (Å³)	1417.5 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.99
Crystal size (mm)	0.29 × 0.25 × 0.18

Data collection
Diffractometer	Bruker APEX-II area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.763, 0.842
No. of measured, independent and observed [I > 2σ(I)] reflections	7535, 2649, 2349
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.090, 1.06
No. of reflections	2649
No. of parameters	184
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.64, −0.30

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997), SHELXL97.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O7W	0.82	1.95	2.760 (3)	170.2
O1W—H1WB···O4	0.82	1.85	2.675 (2)	176.4
O2W—H2WA···O4Wⁱ	0.81	2.16	2.948 (2)	163.2
O2W—H2WA···O1ⁱ	0.81	2.64	3.061 (2)	113.7
O2W—H2WB···O1Wⁱⁱ	0.80	2.63	3.293 (3)	141.5
O3W—H3WB···O6W	0.83	2.00	2.818 (2)	170.6
O3W—H3WA···O3ⁱⁱⁱ	0.81	1.89	2.696 (2)	171.7
O4W—H4WA···O2ⁱ	0.81	2.00	2.8162 (19)	173.9
O4W—H4WB···O3^iv	0.82	1.94	2.758 (2)	178.3
O5W—H5WA···O2^iv	0.82	1.95	2.759 (2)	168.9
O5W—H5WB···O7W^v	0.82	1.93	2.744 (2)	172.6
O6W—H6WA···O4ⁱⁱ	0.87	1.81	2.677 (2)	174.2
O6W—H6WB···O2ⁱ	0.87	2.03	2.894 (2)	175.3
O7W—H7WB···N1^vi	0.91	1.96	2.859 (3)	173.7
O7W—H7WA···O6W^vii	0.87	1.92	2.780 (3)	169.2

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

Acknowledgements

The authors are grateful to SiChuan University for financial support.

References

Bruker (2004). APEX2 (Version 1.22), SAINT (Version 6.0) and SADABS (Version 2004/1). Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Oak Ridge, Tennessee, U.SA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Gokel, G. W., Leevy, W. M. & Weber, W. E. (2004). Chem. Rev. 104, 2723–2750. Web of Science CrossRef PubMed CAS Google Scholar
Lassahn, P.-G., Lozan, V., Timco, G. A., Christian, P., Janiak, C. & Winpenny, R. E. P. (2004). J. Catal. 222, 260–267. Web of Science CrossRef CAS Google Scholar
Liu, -Q. Y. & Xu, L. (2005). Eur. J. Inorg. Chem. pp. 3458–3466. Web of Science CSD CrossRef Google Scholar
Shan, B. Z., Zhao, O., Goswami, N., Eichhorn, D. M. & Rillema, D. P. (2001). Coord. Chem. Rev. 211, 117–144. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar
Wang, J., Lu, L., Bai, J.-W. & Zhong, B.-Z. (2007). Acta Cryst. E63, o4414. Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.