Poly[[aqua­(μ-4,4′-bipyridyl-κ2N:N′)bis­(μ-formato-κ2O:O′)iron(II)] tetra­hydrate]

Jiang, B.; Liu, Z.

doi:10.1107/S1600536809034722

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Pages m1189-m1190

doi:10.1107/S1600536809034722

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Poly[[aqua(μ-4,4′-bipyridyl-κ²N:N′)bis(μ-formato-κ²O:O′)iron(II)] tetrahydrate]

Bin Jiang ^a and Zhilu Liu ^b ^*

^aDepartment of Pharmacy, Shandong Medical College, Jinan 250002, People's Republic of China, and ^bState Key Laboratory of Solid Lubrication, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 73000, People's Republic of China
^*Correspondence e-mail: liuzhilu2009@yahoo.com.cn

(Received 14 August 2009; accepted 29 August 2009; online 9 September 2009)

In the title compound, {[Fe(CHO₂)₂(C₁₀H₈N₂)(H₂O)]·4H₂O}_n, the Fe^II ion is coordinated by two 4,4′-bipyridyl (4,4′-bpy) ligands, three formate ligands and one water molecule. The slightly distorted octahedral FeN₂O₄ coordination results from the N atoms of two bridging 4,4′-bpy ligands, the O atoms of two bridging HCOO⁻ anions of anti–anti mode, all in trans positions around the metal centre, and the O atoms of one terminal HCOO⁻ anion and of one water molecule. The bridging formate ligands link the metal ions into chains that are further connected via 4,4′-bpy ligands into a framework structure. The three-dimensional structure is stabilized by extensive O—H⋯O hydrogen bonding. The crystals were twinned containing a 0.84:0.16 racemate.

Related literature

For the potential applications of metal-organic frameworks, see: Jia et al. (2007 ); Hagrman et al. (1999 ); Kortz et al. (2003 ); Li et al. (1996 ); Liu et al. (2007 ); Seo et al. (2000 ); Wang et al. (2007 ); Yaghi et al. (1998 ).

Experimental

Crystal data

[Fe(CHO₂)₂(C₁₀H₈N₂)(H₂O)]·4H₂O
M_r = 392.15
Monoclinic, C c
a = 10.5021 (6) Å
b = 20.1959 (11) Å
c = 8.1256 (4) Å
β = 102.367 (1)°
V = 1683.44 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.94 mm⁻¹
T = 273 K
0.12 × 0.10 × 0.08 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.895, T_max = 0.928
4376 measured reflections
2523 independent reflections
2468 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.084
S = 1.00
2523 reflections
248 parameters
19 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.42 e Å⁻³
Absolute structure: Flack (1983 ), 1036 Friedel pairs
Flack parameter: 0.158 (18)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H1W⋯O4ⁱ	0.82 (4)	1.97 (4)	2.693 (4)	146 (6)
O6—H3W⋯O3ⁱⁱ	0.82 (4)	1.98 (4)	2.792 (4)	173 (4)
O6—H4W⋯O9ⁱⁱⁱ	0.82 (3)	1.93 (3)	2.753 (4)	175 (5)
O7—H5W⋯O8^iv	0.82 (5)	2.22 (5)	3.028 (9)	171 (4)
O7—H6W⋯O4ⁱⁱ	0.82 (3)	2.46 (3)	3.117 (7)	137 (4)
O9—H10W⋯O1ⁱⁱⁱ	0.82 (4)	2.16 (4)	2.954 (4)	165 (5)
O7—H6W⋯O2	0.82 (3)	2.61 (5)	3.158 (5)	125 (5)
O8—H7W⋯O7	0.82 (3)	1.94 (3)	2.763 (7)	174 (5)
O8—H8W⋯O6	0.82 (3)	2.031 (19)	2.797 (5)	155 (4)
O9—H9W⋯O8	0.82 (4)	1.99 (4)	2.779 (5)	163 (5)
O5—H2W⋯O6	0.82 (3)	1.94 (4)	2.729 (4)	161 (4)
Symmetry codes: (i) x, y, z+1; (ii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[x, -y+1, z+{\script{1\over 2}}]$ ; (iv) $[x, -y+1, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809034722/pv2199sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809034722/pv2199Isup2.hkl

checkCIF report

Comment top

Design and construction of metal-organic frameworks (MOFs) have attracted considerable attention in recent years, not only for their intriguing structural motifs but also for their potential applications in the areas of catalysis, separation, gas absorption, molecular recognition, nonlinear optics, and magnetochemistry (Jia et al., 2007; Li et al., 1996; Seo et al., 2000; Hagrman et al., 1999; Yaghi et al., 1998; Kortz et al., 2003; Liu et al., 2007; Wang et al., 2007). A successful strategy for the design and synthesis of predictable MOFs is the assembly reaction between metal ions and well designed organic ligands. In this paper, we report the preparation and crystal structure of the title compound, (I).

The Fe^II ion in the title compound (Fig. 1) is octahedrally coordinated by two bridging 4,4'-bipyridyl (4,4'-bpy) ligands, two bridging HCOO^- (O1—C1—O2) groups in an anti-anti mode, all in trans positions around the metal ion, one terminal HCOO^- (O3—C2—O4), and one H₂O molecule. The bridging formate ligands link metal ions to form chains running along the ac direction. The chain is further connected to other chains via 4,4'-bpy ligands. The three-dimensional structure is stabilized by extensive hydrogen bonding (Fig. 2 and Table 1).

Related literature top

For the potential applications of metal-organic frameworks, see: Jia et al. (2007); Hagrman et al. (1999); Kortz et al. (2003); Li et al. (1996); Liu et al. (2007); Seo et al. (2000); Wang et al. (2007); Yaghi et al. (1998).

Experimental top

The crystallization was performed in a 25 ml Teflon-lined stainless steel vessel. A mixture of 4,4'-bipyridyl ligand (1 mmol), iron(II) chloride tetrahydrate (1 mmol), and sodium formate (1 mmol) in 14 ml water was heated to 443 K, and kept at this temperature for one day. Green crystals were obtained after cooling to room temperature with the yield 75%.

Computing details top

Data collection: SMART (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the title compound with the atom-labeling scheme. Displacement ellipsoids are drawn at the 30% probability level. Symmetry codes for atoms: N1A, x+1/2, -y+3/2, z+1/2 and O2B, x+1/2, y-1/2, z.
	Fig. 2. Packing diagram of the title compound showing hydrogen bonding; H-atoms not involved in H-bonds have been excluded for clarity.

Poly[[aqua(µ-4,4'-bipyridyl-κ²N:N')-µ-formato- κ²O:O'-formato-κO-iron(II)] tetrahydrate] top

Crystal data top

[Fe(CHO₂)₂(C₁₀H₈N₂)(H₂O)]·4H₂O	F(000) = 816
M_r = 392.15	D_x = 1.547 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 4008 reflections
a = 10.5021 (6) Å	θ = 2.2–28.3°
b = 20.1959 (11) Å	µ = 0.94 mm⁻¹
c = 8.1256 (4) Å	T = 273 K
β = 102.367 (1)°	Block, green
V = 1683.44 (16) Å³	0.12 × 0.10 × 0.08 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	2523 independent reflections
Radiation source: fine-focus sealed tube	2468 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −12→11
T_min = 0.895, T_max = 0.928	k = −19→24
4376 measured reflections	l = −9→9

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)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.084	w = 1/[σ²(F_o²) + (0.071P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.001
2523 reflections	Δρ_max = 0.31 e Å⁻³
248 parameters	Δρ_min = −0.42 e Å⁻³
19 restraints	Absolute structure: Flack (1983), 1036 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.158 (18)

Crystal data top

[Fe(CHO₂)₂(C₁₀H₈N₂)(H₂O)]·4H₂O	V = 1683.44 (16) Å³
M_r = 392.15	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 10.5021 (6) Å	µ = 0.94 mm⁻¹
b = 20.1959 (11) Å	T = 273 K
c = 8.1256 (4) Å	0.12 × 0.10 × 0.08 mm
β = 102.367 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2523 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2468 reflections with I > 2σ(I)
T_min = 0.895, T_max = 0.928	R_int = 0.031
4376 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.084	Δρ_max = 0.31 e Å⁻³
S = 1.00	Δρ_min = −0.42 e Å⁻³
2523 reflections	Absolute structure: Flack (1983), 1036 Friedel pairs
248 parameters	Absolute structure parameter: 0.158 (18)
19 restraints

Special details top

Experimental. Elemental Analysis. Calc. for C₁₂H₂₀FeN₂O₉: C 36.73, H 5.10, N 12.24%; Found: C 36.65, H 5.02, N 12.14%.

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
Fe1	0.99831 (11)	0.753902 (16)	0.64202 (13)	0.01649 (13)
C1	0.7398 (3)	0.72764 (15)	0.4049 (4)	0.0274 (6)
H1	0.7212	0.7713	0.4273	0.033*
C2	1.0318 (4)	0.76341 (18)	0.2832 (5)	0.0339 (8)
H2	0.9801	0.7256	0.2686	0.041*
C3	0.7896 (3)	0.85353 (16)	0.6887 (5)	0.0342 (7)
H3	0.7527	0.8158	0.7245	0.041*
C4	0.7264 (3)	0.91325 (17)	0.6933 (4)	0.0338 (7)
H4	0.6487	0.9149	0.7306	0.041*
C5	0.7789 (3)	0.97064 (15)	0.6424 (4)	0.0294 (8)
C6	0.8935 (4)	0.96383 (17)	0.5850 (5)	0.0401 (9)
H6	0.9321	1.0007	0.5475	0.048*
C7	0.9502 (4)	0.90224 (16)	0.5837 (5)	0.0381 (8)
H7	1.0269	0.8989	0.5445	0.046*
C8	0.7165 (3)	1.03639 (15)	0.6479 (4)	0.0280 (7)
C9	0.5937 (3)	1.04287 (16)	0.6846 (5)	0.0359 (8)
H9	0.5493	1.0055	0.7090	0.043*
C10	0.5377 (3)	1.10457 (17)	0.6847 (5)	0.0355 (8)
H10	0.4555	1.1076	0.7096	0.043*
C11	0.7777 (4)	1.09450 (16)	0.6157 (5)	0.0355 (8)
H11	0.8609	1.0932	0.5932	0.043*
C12	0.7138 (3)	1.15402 (16)	0.6174 (4)	0.0327 (8)
H12	0.7559	1.1923	0.5938	0.039*
N1	0.5956 (3)	1.16024 (12)	0.6509 (3)	0.0276 (6)
N2	0.9005 (3)	0.84703 (12)	0.6360 (3)	0.0267 (6)
O1	0.8405 (2)	0.70271 (10)	0.4923 (3)	0.0311 (5)
O2	0.6621 (2)	0.69888 (11)	0.2902 (3)	0.0305 (5)
O3	1.0696 (2)	0.78393 (11)	0.4317 (3)	0.0330 (5)
O4	1.0559 (3)	0.78812 (16)	0.1566 (4)	0.0569 (8)
O5	0.9382 (3)	0.73151 (14)	0.8633 (3)	0.0370 (6)
O6	0.7891 (3)	0.63516 (14)	0.9637 (4)	0.0482 (6)
O7	0.6017 (4)	0.5754 (3)	0.4995 (8)	0.1160 (19)
O8	0.7346 (5)	0.51513 (19)	0.7912 (5)	0.0972 (14)
O9	0.8996 (3)	0.40816 (15)	0.7836 (4)	0.0561 (8)
H1W	0.946 (5)	0.7580 (16)	0.942 (5)	0.080*
H2W	0.892 (4)	0.6994 (13)	0.871 (5)	0.080*
H3W	0.727 (3)	0.660 (2)	0.963 (5)	0.080*
H4W	0.822 (5)	0.620 (2)	1.057 (3)	0.080*
H5W	0.644 (5)	0.5542 (19)	0.444 (7)	0.080*
H6W	0.626 (5)	0.6138 (10)	0.518 (7)	0.080*
H7W	0.692 (4)	0.531 (2)	0.703 (3)	0.080*
H8W	0.761 (5)	0.5426 (16)	0.865 (4)	0.080*
H9W	0.850 (4)	0.4397 (15)	0.764 (6)	0.080*
H10W	0.885 (5)	0.383 (2)	0.856 (5)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.0162 (2)	0.01436 (18)	0.0163 (2)	0.00272 (16)	−0.00227 (13)	−0.00061 (15)
C1	0.0252 (14)	0.0238 (13)	0.0303 (15)	−0.0001 (15)	−0.0001 (12)	0.0005 (15)
C2	0.0352 (19)	0.0367 (16)	0.030 (2)	−0.0028 (15)	0.0070 (15)	−0.0049 (15)
C3	0.037 (2)	0.0232 (16)	0.0437 (18)	0.0014 (14)	0.0122 (15)	0.0034 (13)
C4	0.0307 (19)	0.0267 (17)	0.045 (2)	0.0046 (13)	0.0110 (14)	0.0010 (13)
C5	0.028 (2)	0.0250 (16)	0.0321 (17)	0.0044 (12)	0.0001 (14)	−0.0016 (12)
C6	0.040 (2)	0.0225 (17)	0.061 (2)	0.0034 (13)	0.0188 (18)	0.0044 (15)
C7	0.0352 (19)	0.0268 (16)	0.056 (2)	0.0049 (13)	0.0171 (15)	−0.0004 (15)
C8	0.032 (2)	0.0226 (15)	0.0276 (16)	0.0048 (12)	0.0014 (14)	0.0007 (12)
C9	0.0319 (18)	0.0238 (16)	0.053 (2)	0.0017 (12)	0.0111 (16)	0.0050 (14)
C10	0.0259 (18)	0.0288 (16)	0.053 (2)	0.0048 (12)	0.0121 (15)	0.0011 (14)
C11	0.0274 (18)	0.0280 (17)	0.051 (2)	0.0042 (13)	0.0073 (15)	0.0010 (14)
C12	0.0303 (18)	0.0231 (16)	0.0438 (19)	0.0005 (12)	0.0059 (15)	0.0011 (13)
N1	0.0275 (13)	0.0231 (13)	0.0300 (13)	0.0046 (10)	0.0009 (11)	0.0000 (10)
N2	0.0266 (14)	0.0217 (13)	0.0295 (13)	0.0040 (10)	0.0005 (11)	−0.0010 (10)
O1	0.0256 (12)	0.0278 (11)	0.0339 (12)	0.0014 (9)	−0.0067 (10)	−0.0007 (9)
O2	0.0278 (11)	0.0285 (12)	0.0290 (12)	0.0007 (9)	−0.0079 (10)	−0.0037 (9)
O3	0.0379 (13)	0.0348 (13)	0.0252 (12)	−0.0003 (10)	0.0040 (10)	−0.0025 (9)
O4	0.0724 (19)	0.070 (2)	0.0291 (13)	−0.0197 (15)	0.0119 (12)	−0.0044 (13)
O5	0.0461 (16)	0.0362 (13)	0.0292 (13)	−0.0115 (12)	0.0090 (11)	−0.0025 (11)
O6	0.0475 (15)	0.0446 (15)	0.0538 (17)	0.0017 (11)	0.0134 (12)	0.0059 (12)
O7	0.089 (3)	0.092 (3)	0.161 (6)	−0.021 (3)	0.013 (3)	0.057 (3)
O8	0.124 (4)	0.068 (3)	0.086 (3)	0.017 (2)	−0.008 (2)	−0.020 (2)
O9	0.063 (2)	0.0502 (18)	0.0540 (18)	−0.0072 (14)	0.0096 (15)	0.0084 (13)

Geometric parameters (Å, º) top

Fe1—O5	2.079 (3)	C8—C9	1.390 (5)
Fe1—O3	2.097 (3)	C8—C11	1.390 (5)
Fe1—O1	2.105 (2)	C9—C10	1.378 (5)
Fe1—O2ⁱ	2.105 (2)	C9—H9	0.9300
Fe1—N2	2.139 (3)	C10—N1	1.334 (4)
Fe1—N1ⁱⁱ	2.144 (3)	C10—H10	0.9300
C1—O1	1.247 (4)	C11—C12	1.378 (5)
C1—O2	1.243 (4)	C11—H11	0.9300
C1—H1	0.9300	C12—N1	1.333 (5)
C2—O4	1.218 (5)	C12—H12	0.9300
C2—O3	1.257 (4)	N1—Fe1ⁱⁱⁱ	2.144 (3)
C2—H2	0.9300	O2—Fe1^iv	2.105 (2)
C3—N2	1.330 (4)	O5—H1W	0.82 (4)
C3—C4	1.381 (5)	O5—H2W	0.82 (3)
C3—H3	0.9300	O6—H3W	0.82 (4)
C4—C5	1.384 (5)	O6—H4W	0.82 (3)
C4—H4	0.9300	O7—H5W	0.82 (5)
C5—C6	1.388 (5)	O7—H6W	0.82 (3)
C5—C8	1.486 (4)	O8—H7W	0.82 (3)
C6—C7	1.380 (5)	O8—H8W	0.82 (3)
C6—H6	0.9300	O9—H9W	0.82 (4)
C7—N2	1.338 (4)	O9—H10W	0.82 (4)
C7—H7	0.9300

O5—Fe1—O3	174.46 (10)	N2—C7—H7	118.3
O5—Fe1—O1	92.60 (10)	C6—C7—H7	118.3
O3—Fe1—O1	92.62 (10)	C9—C8—C11	116.7 (3)
O5—Fe1—O2ⁱ	88.06 (9)	C9—C8—C5	121.7 (3)
O3—Fe1—O2ⁱ	86.81 (9)	C11—C8—C5	121.6 (3)
O1—Fe1—O2ⁱ	177.17 (10)	C10—C9—C8	120.0 (3)
O5—Fe1—N2	88.72 (11)	C10—C9—H9	120.0
O3—Fe1—N2	88.90 (10)	C8—C9—H9	120.0
O1—Fe1—N2	95.96 (9)	N1—C10—C9	123.3 (3)
O2ⁱ—Fe1—N2	86.81 (10)	N1—C10—H10	118.4
O5—Fe1—N1ⁱⁱ	90.57 (11)	C9—C10—H10	118.4
O3—Fe1—N1ⁱⁱ	91.81 (10)	C12—C11—C8	119.3 (3)
O1—Fe1—N1ⁱⁱ	84.07 (9)	C12—C11—H11	120.4
O2ⁱ—Fe1—N1ⁱⁱ	93.18 (10)	C8—C11—H11	120.4
N2—Fe1—N1ⁱⁱ	179.28 (13)	N1—C12—C11	124.1 (3)
O1—C1—O2	125.4 (3)	N1—C12—H12	117.9
O1—C1—H1	117.3	C11—C12—H12	117.9
O2—C1—H1	117.3	C12—N1—C10	116.6 (3)
O4—C2—O3	126.6 (4)	C12—N1—Fe1ⁱⁱⁱ	122.3 (2)
O4—C2—H2	116.7	C10—N1—Fe1ⁱⁱⁱ	121.0 (2)
O3—C2—H2	116.7	C3—N2—C7	116.6 (3)
N2—C3—C4	123.6 (3)	C3—N2—Fe1	121.9 (2)
N2—C3—H3	118.2	C7—N2—Fe1	121.4 (2)
C4—C3—H3	118.2	C1—O1—Fe1	126.7 (2)
C3—C4—C5	119.9 (3)	C1—O2—Fe1^iv	122.8 (2)
C3—C4—H4	120.1	C2—O3—Fe1	126.3 (2)
C5—C4—H4	120.1	Fe1—O5—H1W	122 (3)
C4—C5—C6	116.6 (3)	Fe1—O5—H2W	122 (3)
C4—C5—C8	122.2 (3)	H1W—O5—H2W	115 (4)
C6—C5—C8	121.3 (3)	H3W—O6—H4W	114 (4)
C7—C6—C5	119.9 (3)	H5W—O7—H6W	114 (5)
C7—C6—H6	120.1	H7W—O8—H8W	114 (4)
C5—C6—H6	120.1	H9W—O9—H10W	115 (5)
N2—C7—C6	123.4 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H1W···O4^v	0.82 (4)	1.97 (4)	2.693 (4)	146 (6)
O6—H3W···O3^vi	0.82 (4)	1.98 (4)	2.792 (4)	173 (4)
O6—H4W···O9^vii	0.82 (3)	1.93 (3)	2.753 (4)	175 (5)
O7—H5W···O8^viii	0.82 (5)	2.22 (5)	3.028 (9)	171 (4)
O7—H6W···O4^vi	0.82 (3)	2.46 (3)	3.117 (7)	137 (4)
O9—H10W···O1^vii	0.82 (4)	2.16 (4)	2.954 (4)	165 (5)
O7—H6W···O2	0.82 (3)	2.61 (5)	3.158 (5)	125 (5)
O8—H7W···O7	0.82 (3)	1.94 (3)	2.763 (7)	174 (5)
O8—H8W···O6	0.82 (3)	2.03 (2)	2.797 (5)	155 (4)
O9—H9W···O8	0.82 (4)	1.99 (4)	2.779 (5)	163 (5)
O5—H2W···O6	0.82 (3)	1.94 (4)	2.729 (4)	161 (4)

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

Experimental details

Crystal data
Chemical formula	[Fe(CHO₂)₂(C₁₀H₈N₂)(H₂O)]·4H₂O
M_r	392.15
Crystal system, space group	Monoclinic, Cc
Temperature (K)	273
a, b, c (Å)	10.5021 (6), 20.1959 (11), 8.1256 (4)
β (°)	102.367 (1)
V (Å³)	1683.44 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.94
Crystal size (mm)	0.12 × 0.10 × 0.08

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.895, 0.928
No. of measured, independent and observed [I > 2σ(I)] reflections	4376, 2523, 2468
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.084, 1.00
No. of reflections	2523
No. of parameters	248
No. of restraints	19
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.42
Absolute structure	Flack (1983), 1036 Friedel pairs
Absolute structure parameter	0.158 (18)

Computer programs: SMART (Bruker, 2005), SAINT (Bruker, 2005), 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
O5—H1W···O4ⁱ	0.82 (4)	1.97 (4)	2.693 (4)	146 (6)
O6—H3W···O3ⁱⁱ	0.82 (4)	1.98 (4)	2.792 (4)	173 (4)
O6—H4W···O9ⁱⁱⁱ	0.82 (3)	1.93 (3)	2.753 (4)	175 (5)
O7—H5W···O8^iv	0.82 (5)	2.22 (5)	3.028 (9)	171 (4)
O7—H6W···O4ⁱⁱ	0.82 (3)	2.46 (3)	3.117 (7)	137 (4)
O9—H10W···O1ⁱⁱⁱ	0.82 (4)	2.16 (4)	2.954 (4)	165 (5)
O7—H6W···O2	0.82 (3)	2.61 (5)	3.158 (5)	125 (5)
O8—H7W···O7	0.82 (3)	1.94 (3)	2.763 (7)	174 (5)
O8—H8W···O6	0.82 (3)	2.031 (19)	2.797 (5)	155 (4)
O9—H9W···O8	0.82 (4)	1.99 (4)	2.779 (5)	163 (5)
O5—H2W···O6	0.82 (3)	1.94 (4)	2.729 (4)	161 (4)

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

Acknowledgements

This work was supported by the Chinese Academy of Sciences (`Hundred Talents Program') and the Ministry of Science and Technology of China (project of `973' plan, No. 2007CB607606)

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