Poly[bis­(4,4′-bipyridine)(μ3-4,4′-dicarboxybiphenyl-3,3′-di­carboxyl­ato)iron(II)]

Meng, Q.-H.; Lai, H.-L.; Lu, H.; Luo, Y.-F.; Zeng, R.-H.

doi:10.1107/S1600536809046273

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Pages m1537-m1538

doi:10.1107/S1600536809046273

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Poly[bis(4,4′-bipyridine)(μ₃-4,4′-dicarboxybiphenyl-3,3′-dicarboxylato)iron(II)]

Qun-Hui Meng,^a Hui-Ling Lai,^a Han Lu,^a Yi-Fan Luo ^a ^* and Rong-Hua Zeng ^a,^b

^aSchool of Chemistry and Environment, South China Normal University, Guangzhou 510006, People's Republic of China, and ^bSouth China Normal University, Key Laboratory of Technology of Electrochemical Energy Storage and Power Generation, in Guangdong Universities, Guangzhou 510006, People's Republic of China
^*Correspondence e-mail: luoyf2004@yahoo.com.cn

(Received 25 October 2009; accepted 3 November 2009; online 7 November 2009)

In the polymeric title complex, [Fe(C₁₆H₈O₈)(C₁₀H₈N₂)₂]_n, the iron(II) cation is coordinated by four O atoms from three different 4,4′-dicarboxybiphenyl-3,3′-dicarboxylate ligands and two N atoms from two 4,4′-bipyridine ligands in a distorted octahedral geometry. The 4,4′-dicarboxybiphenyl-3,3′-dicarboxylate ligands bridge adjacent cations, forming chains parallel to the c axis. The chains are further connected by intermolecular O—H⋯N hydrogen bonds, forming two-dimensional supramolecular layers parallel to (010).

Related literature

For general background to self-assembling coordination polymers, see: Li et al. (2008 ); Yaghi et al. (2003 ). For related structures, see: Li et al. (2009 ); Liu et al. (2009 ); Wang et al. (2007 ).

Experimental

Crystal data

[Fe(C₁₆H₈O₈)(C₁₀H₈N₂)₂]
M_r = 696.44
Monoclinic, P 2₁ /c
a = 11.9569 (13) Å
b = 24.114 (3) Å
c = 10.7232 (12) Å
β = 105.855 (1)°
V = 2974.2 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.57 mm⁻¹
T = 296 K
0.23 × 0.21 × 0.19 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.880, T_max = 0.899
15189 measured reflections
5363 independent reflections
4293 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.100
S = 1.03
5363 reflections
444 parameters
H-atom parameters constrained
Δρ_max = 0.71 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5⋯N2ⁱ	0.82	1.86	2.677 (2)	171
O3—H3⋯N4ⁱⁱ	0.82	1.81	2.598 (3)	162
Symmetry codes: (i) x-1, y, z-2; (ii) x+1, y, z+1.

Data collection: APEX2 (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: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809046273/rz2381sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809046273/rz2381Isup2.hkl

checkCIF report

Comment top

The construction of self-assembling coordination polymers is of current interest in the fields of supramolecular chemistry and crystal engineering, because of their potential applications in gas storage, molecular sieves, ion exchange, catalysis, magnetism, nonlinearoptics, and molecular sensing (Li et al., 2008; Yaghi et al., 2003). Due to the presence of four carboxylic groups, 4,4'-dicarboxybiphenyl-3,3'-dicarboxylate ligands are promising building blocks for the construction of novel metal-organic coordination polymers (Li et al., 2009; Liu et al., 2009; Wang et al., 2007). Herein, we report the title new metal-organic framework, which was synthesized under hydrothermal conditions.

In the title complex (Fig. 1), each iron(II) atom exhibits a distorted octahedral geometry, defined by four oxygen atoms from three different 4,4'-dicarboxybiphenyl-3,3'-dicarboxylate ligands and two nitrogen atoms from two different 4,4'-bipyridine ligands. The Fe—O and Fe—N distances range from 2.0244 (1) to 2.3327 (1) Å and 2.2201 (1) to 2.2615 (1) Å, respectively, while the O—Fe—O angles and N—Fe—O angles fall in the range from 58.64 (6) to 160.43 (7) %A and 82.29 (6) to 102.91 (7) %A, respectively. The dihedral angles between the N1/C1–C5 and N2/C6–C10, N3/C11–C15 and N4/C16–C20, C22/C23/C25–c28 and C29–C32/C33/C34 are 25.74 (8), 26.91 (9) and 37.39 (7)°, respectively. Adjacent metal centres are connected by the 4,4'-dicarboxybiphenyl-3,3'-dicarboxylate ligands to form chains (Fig. 2) running parallel to the c axis. Intermolecular O—H···N hydrogen bonds (Table 1) link the chains into two-dimensional supramolecular layers parallel to (0 1 0) (Fig. 3).

Related literature top

For general background to self-assembling coordination polymers, see: Li et al. (2008); Yaghi et al. (2003). For related structures, see: Li et al. (2009); Liu et al. (2009); Wang et al. (2007).

Experimental top

A mixture of FeSO₄.7H₂O (0.139 g, 0.5mmol), 4,4'-bipyridine (0.078 g; 0.5 mmol), biphenyl-3,3',-4,4'-tetracarboxylic acid (0.165 g; 0.5 mmol), water (10mL) were stirred vigorously for 30 min and then sealed in a Teflon-lined stainless-steel autoclave (25 mL capacity). The autoclave was heated and maintained at 423K for 3 days, then cooled to room temperature at 5Kh^-1. Red block crystals suitable for X-ray analysis were obtained.

Computing details top

Data collection: APEX2 (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: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound showing the atomic-numbering scheme. Displacement ellipsoids drawn at the 30% probability level. H atoms are omitted for clarity. [Symmetry codes: (#1) x, y, 1+z; (#2) 1-x, 2-y, 1-z]
	Fig. 2. Partial crystal packing of the title compound showing a one-dimensional chain running parallel to the c axis. 4,4'-Bipyridine ligands are omitted for clarity.
	Fig. 3. Partial crystal packing of the title compound showing the two-dimensional supramolecular layers parallel to (0 1 0). Hydrogen bonds are shown as dashed lines.

Poly[bis(4,4'-bipyridine)(µ₃-4,4'-dicarboxybiphenyl-3,3'- dicarboxylato)iron(II)] top

Crystal data top

[Fe(C₁₆H₈O₈)(C₁₀H₈N₂)₂]	F(000) = 1432
M_r = 696.44	D_x = 1.555 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4905 reflections
a = 11.9569 (13) Å	θ = 2.4–27.0°
b = 24.114 (3) Å	µ = 0.57 mm⁻¹
c = 10.7232 (12) Å	T = 296 K
β = 105.855 (1)°	Block, red
V = 2974.2 (6) Å³	0.23 × 0.21 × 0.19 mm
Z = 4

Data collection top

Bruker APEXII area-detector diffractometer	5363 independent reflections
Radiation source: fine-focus sealed tube	4293 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
ϕ and ω scans	θ_max = 25.2°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −14→10
T_min = 0.880, T_max = 0.899	k = −28→26
15189 measured reflections	l = −12→12

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.100	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0462P)² + 1.5067P] where P = (F_o² + 2F_c²)/3
5363 reflections	(Δ/σ)_max = 0.002
444 parameters	Δρ_max = 0.71 e Å⁻³
0 restraints	Δρ_min = −0.46 e Å⁻³

Crystal data top

[Fe(C₁₆H₈O₈)(C₁₀H₈N₂)₂]	V = 2974.2 (6) Å³
M_r = 696.44	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.9569 (13) Å	µ = 0.57 mm⁻¹
b = 24.114 (3) Å	T = 296 K
c = 10.7232 (12) Å	0.23 × 0.21 × 0.19 mm
β = 105.855 (1)°

Data collection top

Bruker APEXII area-detector diffractometer	5363 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	4293 reflections with I > 2σ(I)
T_min = 0.880, T_max = 0.899	R_int = 0.038
15189 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.100	H-atom parameters constrained
S = 1.03	Δρ_max = 0.71 e Å⁻³
5363 reflections	Δρ_min = −0.46 e Å⁻³
444 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.58299 (3)	0.948957 (13)	0.88381 (3)	0.02617 (11)
C27	0.63026 (19)	0.80826 (9)	0.4436 (2)	0.0267 (5)
C11	0.4184 (2)	0.97360 (10)	0.5952 (2)	0.0331 (6)
H11	0.4542	1.0082	0.6064	0.040*
O3	0.88485 (15)	0.84329 (7)	0.88903 (16)	0.0417 (4)
H3	0.9409	0.8416	0.9532	0.063*
C29	0.5469 (2)	0.81316 (9)	0.3128 (2)	0.0277 (5)
N2	1.05946 (18)	0.88387 (10)	1.71537 (19)	0.0416 (5)
C3	0.8429 (2)	0.91461 (10)	1.3316 (2)	0.0322 (5)
O5	0.23281 (15)	0.87426 (7)	−0.06664 (16)	0.0414 (4)
H5	0.1792	0.8734	−0.1333	0.062*
C21	0.6846 (2)	0.88567 (9)	0.7580 (2)	0.0279 (5)
N1	0.70900 (17)	0.93693 (8)	1.07668 (18)	0.0327 (5)
N4	0.0513 (2)	0.85951 (11)	0.0994 (2)	0.0510 (6)
N3	0.44003 (17)	0.93946 (8)	0.69706 (18)	0.0304 (4)
C10	0.9865 (2)	0.85667 (11)	1.4936 (2)	0.0382 (6)
H10	0.9875	0.8309	1.4293	0.046*
C5	0.7413 (2)	0.88541 (11)	1.1179 (2)	0.0388 (6)
H5A	0.7179	0.8564	1.0593	0.047*
C2	0.8088 (2)	0.96780 (11)	1.2899 (2)	0.0435 (7)
H2	0.8296	0.9974	1.3471	0.052*
C6	0.9155 (2)	0.90314 (11)	1.4651 (2)	0.0332 (5)
C1	0.7440 (2)	0.97724 (11)	1.1640 (2)	0.0432 (7)
H1	0.7237	1.0136	1.1386	0.052*
C4	0.8068 (2)	0.87257 (11)	1.2414 (2)	0.0383 (6)
H4	0.8266	0.8359	1.2642	0.046*
C9	1.0557 (2)	0.84914 (12)	1.6183 (2)	0.0414 (6)
H9	1.1026	0.8177	1.6355	0.050*
C7	0.9158 (2)	0.93795 (12)	1.5675 (3)	0.0482 (7)
H7	0.8675	0.9689	1.5544	0.058*
C8	0.9880 (3)	0.92674 (13)	1.6896 (2)	0.0506 (7)
H8	0.9861	0.9506	1.7571	0.061*
C12	0.3463 (2)	0.96087 (10)	0.4744 (2)	0.0338 (6)
H12	0.3344	0.9864	0.4069	0.041*
C16	0.2130 (2)	0.89236 (11)	0.3283 (2)	0.0350 (6)
C14	0.3124 (2)	0.87458 (10)	0.5620 (2)	0.0358 (6)
H14	0.2764	0.8401	0.5547	0.043*
C17	0.1517 (3)	0.93092 (12)	0.2401 (3)	0.0519 (8)
H17	0.1640	0.9687	0.2559	0.062*
C13	0.2917 (2)	0.90935 (10)	0.4548 (2)	0.0313 (5)
C15	0.3853 (2)	0.89073 (10)	0.6785 (2)	0.0345 (6)
H15	0.3973	0.8664	0.7482	0.041*
C20	0.1939 (2)	0.83734 (12)	0.2949 (3)	0.0484 (7)
H20	0.2353	0.8100	0.3495	0.058*
C19	0.1136 (3)	0.82278 (13)	0.1808 (3)	0.0527 (8)
H19	0.1027	0.7854	0.1601	0.063*
C18	0.0727 (3)	0.91279 (14)	0.1290 (3)	0.0622 (9)
H18	0.0318	0.9392	0.0712	0.075*
C26	0.7131 (2)	0.76653 (10)	0.4723 (2)	0.0313 (5)
H26	0.7138	0.7393	0.4112	0.038*
C36	0.51638 (19)	0.86533 (9)	0.2589 (2)	0.0269 (5)
H36	0.5478	0.8966	0.3066	0.032*
C22	0.70735 (19)	0.84500 (9)	0.66113 (19)	0.0246 (5)
C25	0.7947 (2)	0.76543 (10)	0.5919 (2)	0.0305 (5)
H25	0.8516	0.7380	0.6087	0.037*
C34	0.44068 (19)	0.87230 (9)	0.1366 (2)	0.0250 (5)
C23	0.79408 (19)	0.80409 (9)	0.6875 (2)	0.0258 (5)
C33	0.2957 (2)	0.82910 (10)	−0.0585 (2)	0.0344 (6)
C28	0.62884 (19)	0.84684 (9)	0.5393 (2)	0.0284 (5)
H28	0.5733	0.8749	0.5210	0.034*
C30	0.5005 (2)	0.76689 (10)	0.2393 (2)	0.0394 (6)
H30	0.5216	0.7315	0.2717	0.047*
C24	0.8873 (2)	0.80139 (10)	0.8127 (2)	0.0296 (5)
C32	0.3894 (2)	0.82577 (10)	0.0668 (2)	0.0310 (5)
C31	0.4231 (2)	0.77351 (10)	0.1183 (2)	0.0415 (7)
H31	0.3929	0.7422	0.0700	0.050*
O2	0.62783 (14)	0.86750 (7)	0.83378 (14)	0.0317 (4)
O1	0.70685 (16)	0.93579 (7)	0.75185 (16)	0.0382 (4)
O4	0.95713 (16)	0.76380 (8)	0.83860 (17)	0.0479 (5)
O6	0.27834 (18)	0.79341 (8)	−0.14063 (18)	0.0575 (6)
C35	0.43099 (19)	0.92924 (9)	0.0796 (2)	0.0256 (5)
O7	0.45273 (14)	0.93505 (7)	−0.02766 (14)	0.0338 (4)
O8	0.40781 (15)	0.96848 (7)	0.14606 (15)	0.0355 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.0328 (2)	0.02408 (19)	0.01910 (18)	0.00295 (13)	0.00281 (13)	−0.00112 (12)
C27	0.0317 (13)	0.0253 (12)	0.0203 (11)	0.0002 (9)	0.0025 (10)	0.0004 (9)
C11	0.0381 (14)	0.0307 (13)	0.0265 (12)	−0.0020 (10)	0.0023 (10)	−0.0001 (10)
O3	0.0371 (11)	0.0483 (11)	0.0302 (9)	0.0044 (8)	−0.0070 (7)	−0.0103 (8)
C29	0.0330 (13)	0.0271 (12)	0.0209 (11)	0.0031 (10)	0.0036 (10)	0.0012 (9)
N2	0.0345 (12)	0.0527 (14)	0.0309 (12)	−0.0021 (10)	−0.0023 (9)	0.0060 (10)
C3	0.0269 (13)	0.0415 (15)	0.0247 (12)	0.0026 (10)	0.0010 (10)	−0.0004 (10)
O5	0.0370 (11)	0.0463 (11)	0.0307 (10)	0.0071 (8)	−0.0083 (8)	−0.0022 (8)
C21	0.0298 (13)	0.0275 (13)	0.0208 (11)	0.0054 (10)	−0.0024 (9)	−0.0008 (9)
N1	0.0348 (12)	0.0340 (12)	0.0251 (10)	0.0045 (9)	0.0012 (9)	−0.0007 (8)
N4	0.0408 (14)	0.0683 (18)	0.0352 (13)	−0.0011 (12)	−0.0041 (10)	−0.0144 (12)
N3	0.0311 (11)	0.0349 (12)	0.0235 (10)	0.0017 (8)	0.0047 (8)	−0.0001 (8)
C10	0.0369 (15)	0.0401 (15)	0.0328 (13)	0.0020 (11)	0.0014 (11)	0.0013 (11)
C5	0.0485 (16)	0.0371 (14)	0.0241 (12)	0.0025 (12)	−0.0013 (11)	−0.0029 (10)
C2	0.0490 (17)	0.0376 (15)	0.0335 (14)	0.0063 (12)	−0.0065 (12)	−0.0082 (11)
C6	0.0270 (13)	0.0425 (15)	0.0263 (12)	−0.0008 (10)	0.0008 (10)	0.0018 (10)
C1	0.0532 (17)	0.0352 (15)	0.0307 (14)	0.0117 (12)	−0.0062 (12)	0.0001 (11)
C4	0.0473 (16)	0.0349 (14)	0.0259 (12)	0.0050 (11)	−0.0013 (11)	0.0028 (10)
C9	0.0344 (15)	0.0457 (16)	0.0385 (15)	0.0047 (12)	0.0004 (11)	0.0098 (12)
C7	0.0495 (18)	0.0548 (18)	0.0308 (14)	0.0195 (13)	−0.0051 (12)	−0.0021 (12)
C8	0.0538 (18)	0.0607 (19)	0.0289 (14)	0.0114 (15)	−0.0031 (12)	−0.0048 (13)
C12	0.0372 (14)	0.0360 (14)	0.0239 (12)	−0.0020 (11)	0.0013 (10)	0.0044 (10)
C16	0.0298 (13)	0.0428 (15)	0.0279 (12)	−0.0010 (11)	0.0004 (10)	−0.0044 (11)
C14	0.0337 (14)	0.0323 (14)	0.0370 (14)	−0.0048 (10)	0.0020 (11)	0.0009 (11)
C17	0.0584 (19)	0.0431 (17)	0.0396 (16)	0.0095 (14)	−0.0115 (13)	−0.0097 (13)
C13	0.0262 (13)	0.0370 (14)	0.0273 (12)	0.0026 (10)	0.0015 (10)	−0.0040 (10)
C15	0.0354 (14)	0.0371 (14)	0.0283 (12)	−0.0022 (11)	0.0042 (10)	0.0060 (10)
C20	0.0502 (17)	0.0414 (16)	0.0422 (16)	−0.0034 (13)	−0.0067 (13)	−0.0029 (12)
C19	0.0542 (19)	0.0511 (18)	0.0448 (16)	−0.0116 (14)	0.0000 (14)	−0.0133 (14)
C18	0.062 (2)	0.065 (2)	0.0414 (17)	0.0152 (16)	−0.0162 (15)	−0.0066 (15)
C26	0.0390 (14)	0.0292 (13)	0.0233 (11)	0.0060 (10)	0.0048 (10)	−0.0049 (9)
C36	0.0336 (13)	0.0241 (12)	0.0200 (11)	0.0001 (9)	0.0022 (9)	−0.0040 (9)
C22	0.0300 (12)	0.0233 (12)	0.0196 (11)	−0.0002 (9)	0.0050 (9)	0.0009 (8)
C25	0.0345 (13)	0.0278 (12)	0.0271 (12)	0.0094 (10)	0.0048 (10)	0.0008 (9)
C34	0.0285 (12)	0.0258 (12)	0.0188 (11)	0.0029 (9)	0.0034 (9)	−0.0006 (9)
C23	0.0272 (12)	0.0263 (12)	0.0220 (11)	−0.0011 (9)	0.0036 (9)	0.0024 (9)
C33	0.0363 (14)	0.0338 (14)	0.0274 (12)	−0.0049 (11)	−0.0011 (10)	0.0018 (10)
C28	0.0304 (13)	0.0272 (12)	0.0247 (11)	0.0076 (9)	0.0027 (10)	0.0015 (9)
C30	0.0529 (17)	0.0250 (13)	0.0306 (13)	0.0028 (11)	−0.0049 (11)	0.0022 (10)
C24	0.0286 (13)	0.0348 (14)	0.0235 (11)	−0.0014 (10)	0.0039 (10)	0.0030 (10)
C32	0.0354 (13)	0.0296 (13)	0.0237 (11)	−0.0011 (10)	0.0011 (10)	−0.0013 (10)
C31	0.0551 (18)	0.0253 (13)	0.0331 (14)	−0.0048 (11)	−0.0068 (12)	−0.0038 (10)
O2	0.0383 (10)	0.0346 (9)	0.0204 (8)	0.0044 (7)	0.0049 (7)	−0.0013 (7)
O1	0.0517 (11)	0.0256 (9)	0.0346 (9)	0.0016 (8)	0.0076 (8)	−0.0032 (7)
O4	0.0446 (11)	0.0457 (12)	0.0422 (11)	0.0147 (9)	−0.0071 (8)	0.0026 (9)
O6	0.0701 (14)	0.0466 (12)	0.0369 (11)	0.0030 (10)	−0.0176 (9)	−0.0143 (9)
C35	0.0243 (12)	0.0267 (12)	0.0210 (11)	−0.0005 (9)	−0.0017 (9)	−0.0005 (9)
O7	0.0377 (10)	0.0395 (10)	0.0233 (8)	0.0002 (7)	0.0068 (7)	0.0056 (7)
O8	0.0532 (11)	0.0234 (9)	0.0284 (9)	0.0038 (7)	0.0084 (8)	−0.0023 (7)

Geometric parameters (Å, º) top

Fe1—O8ⁱ	2.0244 (17)	C7—C8	1.384 (4)
Fe1—O7ⁱⁱ	2.0609 (16)	C7—H7	0.9300
Fe1—O2	2.1426 (16)	C8—H8	0.9300
Fe1—N1	2.2201 (19)	C12—C13	1.392 (3)
Fe1—N3	2.2615 (19)	C12—H12	0.9300
Fe1—O1	2.3327 (18)	C16—C20	1.377 (4)
C27—C26	1.387 (3)	C16—C17	1.384 (4)
C27—C28	1.389 (3)	C16—C13	1.482 (3)
C27—C29	1.487 (3)	C14—C15	1.370 (3)
C11—N3	1.335 (3)	C14—C13	1.390 (3)
C11—C12	1.381 (3)	C14—H14	0.9300
C11—H11	0.9300	C17—C18	1.374 (4)
O3—C24	1.306 (3)	C17—H17	0.9300
O3—H3	0.8200	C15—H15	0.9300
C29—C36	1.391 (3)	C20—C19	1.379 (4)
C29—C30	1.391 (3)	C20—H20	0.9300
N2—C8	1.321 (4)	C19—H19	0.9300
N2—C9	1.327 (3)	C18—H18	0.9300
C3—C2	1.383 (4)	C26—C25	1.383 (3)
C3—C4	1.386 (3)	C26—H26	0.9300
C3—C6	1.483 (3)	C36—C34	1.385 (3)
O5—C33	1.313 (3)	C36—H36	0.9300
O5—H5	0.8200	C22—C28	1.386 (3)
C21—O1	1.243 (3)	C22—C23	1.403 (3)
C21—O2	1.271 (3)	C25—C23	1.387 (3)
C21—C22	1.506 (3)	C25—H25	0.9300
N1—C1	1.335 (3)	C34—C32	1.395 (3)
N1—C5	1.339 (3)	C34—C35	1.495 (3)
N4—C19	1.321 (4)	C23—C24	1.494 (3)
N4—C18	1.331 (4)	C33—O6	1.208 (3)
N3—C15	1.333 (3)	C33—C32	1.498 (3)
C10—C9	1.379 (3)	C28—H28	0.9300
C10—C6	1.389 (3)	C30—C31	1.382 (3)
C10—H10	0.9300	C30—H30	0.9300
C5—C4	1.378 (3)	C24—O4	1.212 (3)
C5—H5A	0.9300	C32—C31	1.391 (3)
C2—C1	1.380 (3)	C31—H31	0.9300
C2—H2	0.9300	C35—O7	1.254 (3)
C6—C7	1.382 (4)	C35—O8	1.260 (3)
C1—H1	0.9300	O7—Fe1ⁱⁱⁱ	2.0609 (16)
C4—H4	0.9300	O8—Fe1ⁱ	2.0244 (17)
C9—H9	0.9300

O8ⁱ—Fe1—O7ⁱⁱ	108.27 (7)	C13—C12—H12	120.4
O8ⁱ—Fe1—O2	146.50 (7)	C20—C16—C17	116.8 (2)
O7ⁱⁱ—Fe1—O2	103.80 (7)	C20—C16—C13	121.5 (2)
O8ⁱ—Fe1—N1	102.91 (7)	C17—C16—C13	121.6 (2)
O7ⁱⁱ—Fe1—N1	87.46 (7)	C15—C14—C13	120.5 (2)
O2—Fe1—N1	87.76 (7)	C15—C14—H14	119.7
O8ⁱ—Fe1—N3	91.15 (7)	C13—C14—H14	119.7
O7ⁱⁱ—Fe1—N3	84.72 (7)	C18—C17—C16	119.2 (3)
O2—Fe1—N3	82.29 (6)	C18—C17—H17	120.4
N1—Fe1—N3	165.49 (8)	C16—C17—H17	120.4
O8ⁱ—Fe1—O1	88.10 (6)	C14—C13—C12	116.3 (2)
O7ⁱⁱ—Fe1—O1	160.43 (7)	C14—C13—C16	121.0 (2)
O2—Fe1—O1	58.64 (6)	C12—C13—C16	122.6 (2)
N1—Fe1—O1	99.53 (7)	N3—C15—C14	123.4 (2)
N3—Fe1—O1	84.29 (7)	N3—C15—H15	118.3
C26—C27—C28	118.3 (2)	C14—C15—H15	118.3
C26—C27—C29	121.45 (19)	C16—C20—C19	120.1 (3)
C28—C27—C29	120.2 (2)	C16—C20—H20	120.0
N3—C11—C12	124.2 (2)	C19—C20—H20	120.0
N3—C11—H11	117.9	N4—C19—C20	123.1 (3)
C12—C11—H11	117.9	N4—C19—H19	118.5
C24—O3—H3	109.5	C20—C19—H19	118.5
C36—C29—C30	118.1 (2)	N4—C18—C17	123.7 (3)
C36—C29—C27	119.7 (2)	N4—C18—H18	118.1
C30—C29—C27	122.1 (2)	C17—C18—H18	118.1
C8—N2—C9	116.6 (2)	C25—C26—C27	120.0 (2)
C2—C3—C4	116.4 (2)	C25—C26—H26	120.0
C2—C3—C6	121.9 (2)	C27—C26—H26	120.0
C4—C3—C6	121.7 (2)	C34—C36—C29	122.2 (2)
C33—O5—H5	109.5	C34—C36—H36	118.9
O1—C21—O2	121.9 (2)	C29—C36—H36	118.9
O1—C21—C22	121.0 (2)	C28—C22—C23	119.0 (2)
O2—C21—C22	116.4 (2)	C28—C22—C21	115.20 (19)
C1—N1—C5	115.9 (2)	C23—C22—C21	125.58 (19)
C1—N1—Fe1	124.13 (16)	C26—C25—C23	121.8 (2)
C5—N1—Fe1	119.29 (16)	C26—C25—H25	119.1
C19—N4—C18	116.9 (2)	C23—C25—H25	119.1
C15—N3—C11	116.3 (2)	C36—C34—C32	119.2 (2)
C15—N3—Fe1	116.29 (15)	C36—C34—C35	117.16 (19)
C11—N3—Fe1	126.34 (16)	C32—C34—C35	123.08 (19)
C9—C10—C6	119.2 (2)	C25—C23—C22	118.5 (2)
C9—C10—H10	120.4	C25—C23—C24	118.8 (2)
C6—C10—H10	120.4	C22—C23—C24	122.7 (2)
N1—C5—C4	124.2 (2)	O6—C33—O5	124.2 (2)
N1—C5—H5A	117.9	O6—C33—C32	123.6 (2)
C4—C5—H5A	117.9	O5—C33—C32	112.2 (2)
C1—C2—C3	120.4 (2)	C22—C28—C27	122.2 (2)
C1—C2—H2	119.8	C22—C28—H28	118.9
C3—C2—H2	119.8	C27—C28—H28	118.9
C7—C6—C10	116.5 (2)	C31—C30—C29	120.0 (2)
C7—C6—C3	121.9 (2)	C31—C30—H30	120.0
C10—C6—C3	121.6 (2)	C29—C30—H30	120.0
N1—C1—C2	123.4 (2)	O4—C24—O3	124.5 (2)
N1—C1—H1	118.3	O4—C24—C23	122.5 (2)
C2—C1—H1	118.3	O3—C24—C23	113.0 (2)
C5—C4—C3	119.6 (2)	C31—C32—C34	118.6 (2)
C5—C4—H4	120.2	C31—C32—C33	118.0 (2)
C3—C4—H4	120.2	C34—C32—C33	123.4 (2)
N2—C9—C10	124.1 (2)	C30—C31—C32	121.6 (2)
N2—C9—H9	117.9	C30—C31—H31	119.2
C10—C9—H9	117.9	C32—C31—H31	119.2
C6—C7—C8	119.9 (3)	C21—O2—Fe1	93.32 (13)
C6—C7—H7	120.0	C21—O1—Fe1	85.40 (14)
C8—C7—H7	120.0	O7—C35—O8	124.6 (2)
N2—C8—C7	123.5 (3)	O7—C35—C34	117.7 (2)
N2—C8—H8	118.3	O8—C35—C34	117.57 (19)
C7—C8—H8	118.3	C35—O7—Fe1ⁱⁱⁱ	144.35 (15)
C11—C12—C13	119.1 (2)	C35—O8—Fe1ⁱ	128.26 (15)
C11—C12—H12	120.4

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···N2^iv	0.82	1.86	2.677 (2)	171
O3—H3···N4^v	0.82	1.81	2.598 (3)	162

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

Experimental details

Crystal data
Chemical formula	[Fe(C₁₆H₈O₈)(C₁₀H₈N₂)₂]
M_r	696.44
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	11.9569 (13), 24.114 (3), 10.7232 (12)
β (°)	105.855 (1)
V (Å³)	2974.2 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.57
Crystal size (mm)	0.23 × 0.21 × 0.19

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.880, 0.899
No. of measured, independent and observed [I > 2σ(I)] reflections	15189, 5363, 4293
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.100, 1.03
No. of reflections	5363
No. of parameters	444
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.71, −0.46

Computer programs: APEX2 (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—H5···N2ⁱ	0.82	1.86	2.677 (2)	170.7
O3—H3···N4ⁱⁱ	0.82	1.81	2.598 (3)	162.3

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

Acknowledgements

The authors acknowledge the Chan Xue Yan Cooperative Special Project of Guangdong Province and the Ministry of Science and Technology of PRC (No. 2007A090302046), the Project of Science and Technology of Guangdong Province (No. 2007A020200002-4) and the Natural Science Foundation of Guangdong Province (No. 9151063101000037) for supporting this work.

References

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