catena-Poly[bis­[(1,10-phenanthroline)iron(II)]-bis­(μ-5-carboxy­benzene-1,3-dicarboxyl­ato)]

Cheng, L.; Zhang, Y.-W.; Sun, Y.-Y.; Wang, J.-Q.

doi:10.1107/S160053680804018X

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 1| January 2009| Page m14

doi:10.1107/S160053680804018X

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catena-Poly[bis[(1,10-phenanthroline)iron(II)]-bis(μ-5-carboxybenzene-1,3-dicarboxylato)]

Lin Cheng,^a ^* Ya-Wen Zhang,^a Yan-Yan Sun ^a and Jian-Quan Wang ^a

^aSchool of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189, People's Republic of China
^*Correspondence e-mail: cep02chl@yahoo.com.cn

(Received 25 November 2008; accepted 29 November 2008; online 6 December 2008)

The asymmetric unit of the title compound, [Fe(C₉H₄O₆)(C₁₂H₈N₂)(H₂O)]_n, contains one Fe^II cation, one 5-carboxybenzene-1,3-dicarboxylate dianion (Hbtc), one 1,10-phenanthroline (phen) ligand and one water molecule. The Fe^II centre displays a distorted octahedral geometry, being surrounded by one phen ligand, two μ₂-O atoms of two carboxylate groups from two Hbtc ligands, one O atom from one carboxylate of another Hbtc ligand and one terminal water molecule. One carboxylate group ligates two Fe^II cations in a μ_1,1 mode, while the other carboxylate groups bonds to only one Fe atom. The crystal structure is stabilized by O—H⋯O hydrogen bonds.

Related literature

For related structures, see: Plater et al. (2001 ). For general background, see: Yang et al. (2008 ); Bradshaw et al. (2004 ); Chui et al. (1999 ).

Experimental

Crystal data

[Fe(C₉H₄O₆)(C₁₂H₈N₂)(H₂O)]
M_r = 462.19
Triclinic, $[P \overline 1]$
a = 9.5925 (15) Å
b = 10.8971 (16) Å
c = 11.1998 (17) Å
α = 96.221 (3)°
β = 111.320 (2)°
γ = 111.736 (2)°
V = 972.3 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.82 mm⁻¹
T = 293 (2) K
0.25 × 0.22 × 0.18 mm

Data collection

Bruker APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ) T_min = 0.821, T_max = 0.866
7689 measured reflections
3798 independent reflections
3228 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.096
S = 1.05
3798 reflections
292 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.37 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
O1W—H1WA⋯O1ⁱ	0.85 (4)	1.79 (4)	2.602 (3)	159 (3)
O1W—H1WB⋯O4ⁱⁱ	0.80 (4)	1.94 (4)	2.740 (3)	172 (3)
O3—H3A⋯O6ⁱⁱⁱ	0.79 (4)	1.86 (4)	2.622 (3)	160 (4)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+2, -y+2, -z+1; (iii) x+1, y, z.

Data collection: SMART (Bruker, 2000 ); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680804018X/bt2819sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680804018X/bt2819Isup2.hkl

checkCIF report

Comment top

Recent years have witnessed an explosion of great interest in hybrid organic–inorganic framework solids not only for their intriguing architectures and topologies, but also for their potential applications in optical, electrical, magnetic and microporous materials (Yang et al., 2008). And benzene-1,3,5-tricarboxylic acid has been widely used to construct many novel and interesting metal–organic frameworks (Bradshaw et al., 2004; Chui et al., 1999). Herein, we present the synthesis and structural characterization of a new one-dimensional compound [Fe(Hbtc)(phen)]n (H3btc = benzene-1,3,5-tricarboxylic acid; phen = 1,10-phenanthroline) using H3btc as a ligand.

The asymmetric unit of the title compound, contains a Fe^II cation, a dianion of Hbtc and a chelating phen. In the compound, each Fe^II displays a distorted octahedral geometry, being surrounded by one phen ligand, two µ²-O atoms of two carboxylates coming from two Hbtc ligands, one O atom from one carboxylate of another Hbtc and one terminal water molecule. The Hbtc ligand coming from the deprotonation of two carboxylates of H3btc acts as a dianion, in which one carboxylate ligates two Fe^II cations in the µ_1,1 mode with the Fe—O—Fe angle at 102.75 (7)° and Fe···Fe distance of 3.38 (3) Å, to form a Fe₂ unit; while the other carboxylate adopts a monodentate mode. Thus, the adjacent Fe₂ units are linked each other by a pair of tridentate Hbtc ligands in head-to-tail into a one-dimensional chain. The shortest Fe···Fe distance separated by Hbtc ligands is 10.90 (3) Å. Further, the one-dimensional chains are stabled by intrachain hydrogen bonding between coordinated water molecules and adjacent uncoordinated O atoms of monodentate carboxylates with the O···O distance of 2.602 (3) Å. Finally, the one-dimensional chains are further linked together by the interchain hydrogen bonding between uncoordinated carboxylates and uncoordinated O atoms of coordinated µ²-carboxylates as well as coordinated water molecules into a two-dimensional supramolecular network.

Related literature top

For related structures, see: Plater et al. (2001). For general background, see: Yang et al. (2008); Bradshaw et al. (2004); Chui et al. (1999).

Experimental top

A mixture of H₃btc (0.0210 g, 0.1 mmol), phen (0.0180 g, 0.1 mmol), FeCl₂.4H₂O (0.0199 g, 0.1 mmol) and H₂O (8 ml) was heated in a 15 ml Teflon-lined autoclave at 160 ° for 3 d, followed by slow cooling (5 ° h^-1) to room temperature. The resulting mixture was washed with water, and red block crystals were collected and dried in air (yield 32%, 14.8 mg) based on Fe^II].

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The Fe₂ structure of the title compound with 30% thermal ellipsoids. All the H atoms on the C atoms are omitted for clarity. Symmetry codes: a: 1 - x, 2 - y, 1 - z; b: 1 - x, 1 - y, 1 - z; c: x, 1 + y, z.
	Fig. 2. The one-dimensional chain of the title compound. All the H atoms have been omitted for clarity.

catena-Poly[bis[(1,10-phenanthroline)iron(II)]-bis(µ-5-carboxybenzene- 1,3-dicarboxylato)] top

Crystal data top

[Fe(C₉H₄O₆)(C₁₂H₈N₂)(H₂O)]	Z = 2
M_r = 462.19	F(000) = 472
Triclinic, P1	D_x = 1.579 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.5925 (15) Å	Cell parameters from 785 reflections
b = 10.8971 (16) Å	θ = 2.5–28.0°
c = 11.1998 (17) Å	µ = 0.82 mm⁻¹
α = 96.221 (3)°	T = 293 K
β = 111.320 (2)°	Block, red
γ = 111.736 (2)°	0.25 × 0.22 × 0.18 mm
V = 972.3 (3) Å³

Data collection top

Bruker APEX CCD diffractometer	3798 independent reflections
Radiation source: fine-focus sealed tube	3228 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ϕ and ω scans	θ_max = 26.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −11→11
T_min = 0.821, T_max = 0.866	k = −13→13
7689 measured reflections	l = −13→13

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) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0467P)² + 0.209P] where P = (F_o² + 2F_c²)/3
3798 reflections	(Δ/σ)_max < 0.001
292 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

[Fe(C₉H₄O₆)(C₁₂H₈N₂)(H₂O)]	γ = 111.736 (2)°
M_r = 462.19	V = 972.3 (3) Å³
Triclinic, P1	Z = 2
a = 9.5925 (15) Å	Mo Kα radiation
b = 10.8971 (16) Å	µ = 0.82 mm⁻¹
c = 11.1998 (17) Å	T = 293 K
α = 96.221 (3)°	0.25 × 0.22 × 0.18 mm
β = 111.320 (2)°

Data collection top

Bruker APEX CCD diffractometer	3798 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	3228 reflections with I > 2σ(I)
T_min = 0.821, T_max = 0.866	R_int = 0.024
7689 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.37 e Å⁻³
3798 reflections	Δρ_min = −0.22 e Å⁻³
292 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
Fe1	0.61551 (4)	0.98060 (3)	0.64542 (3)	0.02290 (12)
C1	0.4072 (3)	0.4212 (2)	0.3242 (2)	0.0203 (5)
C2	0.5643 (3)	0.4812 (2)	0.3283 (2)	0.0238 (5)
H2A	0.6162	0.4266	0.3174	0.029*
C3	0.6454 (3)	0.6223 (2)	0.3487 (2)	0.0240 (5)
C4	0.5696 (3)	0.7048 (2)	0.3685 (2)	0.0239 (5)
H4A	0.6239	0.7994	0.3829	0.029*
C5	0.4132 (3)	0.6459 (2)	0.3669 (2)	0.0202 (5)
C6	0.3329 (3)	0.5041 (2)	0.3441 (2)	0.0218 (5)
H6A	0.2277	0.4643	0.3421	0.026*
C7	0.3235 (3)	0.2700 (2)	0.3103 (2)	0.0244 (5)
C8	0.8159 (3)	0.6886 (3)	0.3565 (3)	0.0320 (6)
C9	0.3293 (3)	0.7313 (2)	0.3927 (2)	0.0234 (5)
C10	0.2781 (3)	0.8910 (3)	0.6674 (3)	0.0393 (7)
H10A	0.2341	0.8235	0.5880	0.047*
C11	0.1720 (4)	0.8963 (4)	0.7242 (4)	0.0556 (9)
H11A	0.0602	0.8326	0.6841	0.067*
C12	0.2347 (5)	0.9959 (4)	0.8387 (4)	0.0585 (10)
H12A	0.1653	1.0011	0.8773	0.070*
C13	0.4026 (4)	1.0903 (3)	0.8989 (3)	0.0491 (8)
C14	0.4804 (6)	1.1991 (5)	1.0193 (4)	0.0739 (12)
H14A	0.4165	1.2100	1.0615	0.089*
C15	0.6433 (6)	1.2854 (4)	1.0726 (4)	0.0753 (12)
H15A	0.6891	1.3571	1.1492	0.090*
C16	0.7479 (5)	1.2701 (3)	1.0150 (3)	0.0525 (9)
C17	0.9206 (5)	1.3534 (4)	1.0703 (3)	0.0640 (10)
H17A	0.9726	1.4269	1.1465	0.077*
C18	1.0113 (4)	1.3257 (4)	1.0116 (3)	0.0648 (10)
H18A	1.1262	1.3788	1.0487	0.078*
C19	0.9317 (4)	1.2178 (3)	0.8961 (3)	0.0461 (7)
H19A	0.9955	1.2009	0.8568	0.055*
C20	0.6769 (4)	1.1637 (3)	0.8977 (3)	0.0349 (6)
C21	0.5017 (4)	1.0749 (3)	0.8375 (3)	0.0340 (6)
N1	0.4379 (3)	0.9776 (2)	0.7216 (2)	0.0291 (5)
N2	0.7682 (3)	1.1375 (2)	0.8391 (2)	0.0322 (5)
O1	0.1824 (2)	0.22146 (18)	0.3066 (2)	0.0449 (5)
O2	0.4051 (2)	0.20291 (16)	0.30592 (18)	0.0295 (4)
O3	0.8788 (3)	0.6020 (2)	0.3450 (3)	0.0548 (7)
O4	0.8901 (2)	0.8094 (2)	0.3733 (3)	0.0625 (7)
O5	0.42061 (19)	0.86215 (15)	0.44513 (16)	0.0249 (4)
O6	0.1789 (2)	0.67369 (18)	0.3605 (2)	0.0378 (5)
O1W	0.8228 (2)	0.9974 (2)	0.6184 (2)	0.0413 (5)
H1WA	0.847 (4)	0.935 (4)	0.648 (4)	0.073 (12)*
H1WB	0.902 (4)	1.053 (4)	0.613 (3)	0.065 (12)*
H3A	0.971 (5)	0.642 (4)	0.353 (4)	0.093 (15)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.0206 (2)	0.01554 (19)	0.0350 (2)	0.00822 (15)	0.01468 (15)	0.00608 (14)
C1	0.0202 (12)	0.0166 (12)	0.0260 (12)	0.0084 (10)	0.0118 (10)	0.0063 (9)
C2	0.0235 (12)	0.0199 (12)	0.0328 (13)	0.0127 (10)	0.0146 (10)	0.0058 (10)
C3	0.0207 (12)	0.0199 (12)	0.0334 (13)	0.0083 (10)	0.0148 (10)	0.0066 (10)
C4	0.0213 (12)	0.0156 (12)	0.0339 (13)	0.0064 (10)	0.0134 (11)	0.0051 (10)
C5	0.0178 (11)	0.0171 (12)	0.0282 (12)	0.0081 (10)	0.0124 (10)	0.0053 (10)
C6	0.0154 (11)	0.0202 (12)	0.0289 (12)	0.0065 (10)	0.0106 (10)	0.0056 (10)
C7	0.0224 (13)	0.0180 (12)	0.0333 (13)	0.0087 (10)	0.0128 (11)	0.0080 (10)
C8	0.0254 (13)	0.0264 (14)	0.0492 (16)	0.0112 (12)	0.0220 (12)	0.0100 (12)
C9	0.0238 (13)	0.0179 (12)	0.0319 (13)	0.0106 (10)	0.0142 (11)	0.0074 (10)
C10	0.0308 (15)	0.0423 (17)	0.0510 (17)	0.0155 (13)	0.0242 (14)	0.0153 (14)
C11	0.0382 (18)	0.077 (3)	0.073 (2)	0.0316 (18)	0.0369 (18)	0.034 (2)
C12	0.068 (2)	0.090 (3)	0.070 (2)	0.057 (2)	0.056 (2)	0.043 (2)
C13	0.068 (2)	0.062 (2)	0.0497 (19)	0.0456 (19)	0.0408 (18)	0.0234 (17)
C14	0.109 (4)	0.094 (3)	0.062 (2)	0.068 (3)	0.057 (3)	0.021 (2)
C15	0.115 (4)	0.077 (3)	0.049 (2)	0.059 (3)	0.039 (2)	0.001 (2)
C16	0.077 (2)	0.0453 (19)	0.0344 (16)	0.0313 (19)	0.0193 (17)	0.0080 (14)
C17	0.081 (3)	0.042 (2)	0.0379 (18)	0.018 (2)	0.0070 (18)	−0.0034 (15)
C18	0.051 (2)	0.049 (2)	0.049 (2)	0.0016 (17)	−0.0024 (17)	0.0040 (17)
C19	0.0371 (17)	0.0394 (17)	0.0456 (17)	0.0084 (14)	0.0109 (14)	0.0088 (14)
C20	0.0495 (17)	0.0289 (14)	0.0306 (14)	0.0212 (13)	0.0174 (13)	0.0106 (12)
C21	0.0480 (17)	0.0347 (15)	0.0366 (15)	0.0275 (14)	0.0247 (13)	0.0178 (13)
N1	0.0299 (12)	0.0272 (12)	0.0390 (12)	0.0157 (10)	0.0204 (10)	0.0121 (10)
N2	0.0311 (12)	0.0250 (12)	0.0351 (12)	0.0091 (10)	0.0123 (10)	0.0078 (10)
O1	0.0269 (10)	0.0238 (10)	0.0952 (16)	0.0128 (9)	0.0344 (11)	0.0246 (11)
O2	0.0312 (10)	0.0181 (9)	0.0514 (11)	0.0141 (8)	0.0265 (9)	0.0132 (8)
O3	0.0302 (12)	0.0282 (11)	0.116 (2)	0.0128 (10)	0.0452 (13)	0.0108 (12)
O4	0.0372 (12)	0.0277 (12)	0.141 (2)	0.0130 (10)	0.0576 (14)	0.0292 (13)
O5	0.0248 (9)	0.0146 (8)	0.0364 (9)	0.0090 (7)	0.0146 (7)	0.0055 (7)
O6	0.0203 (9)	0.0232 (9)	0.0718 (13)	0.0096 (8)	0.0239 (9)	0.0070 (9)
O1W	0.0315 (11)	0.0269 (11)	0.0819 (16)	0.0154 (10)	0.0366 (11)	0.0248 (11)

Geometric parameters (Å, º) top

Fe1—O1W	2.063 (2)	C11—C12	1.356 (5)
Fe1—O2ⁱ	2.0873 (16)	C11—H11A	0.9300
Fe1—O5ⁱⁱ	2.1554 (15)	C12—C13	1.393 (5)
Fe1—N1	2.157 (2)	C12—H12A	0.9300
Fe1—O5	2.1746 (17)	C13—C21	1.404 (4)
Fe1—N2	2.192 (2)	C13—C14	1.431 (5)
C1—C2	1.384 (3)	C14—C15	1.339 (5)
C1—C6	1.387 (3)	C14—H14A	0.9300
C1—C7	1.502 (3)	C15—C16	1.423 (5)
C2—C3	1.390 (3)	C15—H15A	0.9300
C2—H2A	0.9300	C16—C20	1.402 (4)
C3—C4	1.395 (3)	C16—C17	1.404 (5)
C3—C8	1.487 (3)	C17—C18	1.358 (5)
C4—C5	1.388 (3)	C17—H17A	0.9300
C4—H4A	0.9300	C18—C19	1.388 (4)
C5—C6	1.392 (3)	C18—H18A	0.9300
C5—C9	1.504 (3)	C19—N2	1.329 (3)
C6—H6A	0.9300	C19—H19A	0.9300
C7—O1	1.240 (3)	C20—N2	1.358 (3)
C7—O2	1.262 (3)	C20—C21	1.430 (4)
C8—O4	1.196 (3)	C21—N1	1.352 (3)
C8—O3	1.312 (3)	O2—Fe1ⁱ	2.0873 (16)
C9—O6	1.228 (3)	O3—H3A	0.79 (4)
C9—O5	1.290 (3)	O5—Fe1ⁱⁱ	2.1554 (15)
C10—N1	1.318 (3)	O1W—H1WA	0.85 (4)
C10—C11	1.396 (4)	O1W—H1WB	0.80 (4)
C10—H10A	0.9300

O1W—Fe1—O2ⁱ	89.06 (7)	C12—C11—H11A	120.5
O1W—Fe1—O5ⁱⁱ	96.92 (7)	C10—C11—H11A	120.5
O2ⁱ—Fe1—O5ⁱⁱ	166.10 (7)	C11—C12—C13	120.3 (3)
O1W—Fe1—N1	166.83 (9)	C11—C12—H12A	119.9
O2ⁱ—Fe1—N1	87.61 (7)	C13—C12—H12A	119.9
O5ⁱⁱ—Fe1—N1	89.21 (7)	C12—C13—C21	117.1 (3)
O1W—Fe1—O5	100.00 (8)	C12—C13—C14	124.5 (3)
O2ⁱ—Fe1—O5	89.38 (6)	C21—C13—C14	118.4 (3)
O5ⁱⁱ—Fe1—O5	77.25 (6)	C15—C14—C13	121.4 (3)
N1—Fe1—O5	92.70 (7)	C15—C14—H14A	119.3
O1W—Fe1—N2	92.32 (9)	C13—C14—H14A	119.3
O2ⁱ—Fe1—N2	103.69 (7)	C14—C15—C16	121.6 (3)
O5ⁱⁱ—Fe1—N2	88.65 (7)	C14—C15—H15A	119.2
N1—Fe1—N2	76.12 (8)	C16—C15—H15A	119.2
O5—Fe1—N2	162.22 (7)	C20—C16—C17	117.3 (3)
C2—C1—C6	119.2 (2)	C20—C16—C15	118.8 (3)
C2—C1—C7	120.7 (2)	C17—C16—C15	123.9 (3)
C6—C1—C7	119.9 (2)	C18—C17—C16	119.4 (3)
C1—C2—C3	120.6 (2)	C18—C17—H17A	120.3
C1—C2—H2A	119.7	C16—C17—H17A	120.3
C3—C2—H2A	119.7	C17—C18—C19	119.7 (3)
C2—C3—C4	119.7 (2)	C17—C18—H18A	120.1
C2—C3—C8	121.2 (2)	C19—C18—H18A	120.1
C4—C3—C8	119.0 (2)	N2—C19—C18	122.9 (3)
C5—C4—C3	120.1 (2)	N2—C19—H19A	118.5
C5—C4—H4A	120.0	C18—C19—H19A	118.5
C3—C4—H4A	120.0	N2—C20—C16	122.8 (3)
C4—C5—C6	119.3 (2)	N2—C20—C21	117.4 (2)
C4—C5—C9	122.0 (2)	C16—C20—C21	119.8 (3)
C6—C5—C9	118.73 (19)	N1—C21—C13	122.4 (3)
C1—C6—C5	121.0 (2)	N1—C21—C20	117.5 (2)
C1—C6—H6A	119.5	C13—C21—C20	120.1 (3)
C5—C6—H6A	119.5	C10—N1—C21	118.4 (2)
O1—C7—O2	125.2 (2)	C10—N1—Fe1	126.62 (19)
O1—C7—C1	118.0 (2)	C21—N1—Fe1	114.93 (17)
O2—C7—C1	116.7 (2)	C19—N2—C20	117.7 (2)
O4—C8—O3	122.9 (2)	C19—N2—Fe1	128.4 (2)
O4—C8—C3	123.5 (2)	C20—N2—Fe1	113.40 (17)
O3—C8—C3	113.5 (2)	C7—O2—Fe1ⁱ	129.65 (15)
O6—C9—O5	124.0 (2)	C8—O3—H3A	110 (3)
O6—C9—C5	118.6 (2)	C9—O5—Fe1ⁱⁱ	125.52 (15)
O5—C9—C5	117.3 (2)	C9—O5—Fe1	131.19 (15)
N1—C10—C11	122.7 (3)	Fe1ⁱⁱ—O5—Fe1	102.75 (6)
N1—C10—H10A	118.6	Fe1—O1W—H1WA	106 (2)
C11—C10—H10A	118.6	Fe1—O1W—H1WB	141 (2)
C12—C11—C10	118.9 (3)	H1WA—O1W—H1WB	109 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O1ⁱ	0.85 (4)	1.79 (4)	2.602 (3)	159 (3)
O1W—H1WB···O4ⁱⁱⁱ	0.80 (4)	1.94 (4)	2.740 (3)	172 (3)
O3—H3A···O6^iv	0.79 (4)	1.86 (4)	2.622 (3)	160 (4)

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

Experimental details

Crystal data
Chemical formula	[Fe(C₉H₄O₆)(C₁₂H₈N₂)(H₂O)]
M_r	462.19
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.5925 (15), 10.8971 (16), 11.1998 (17)
α, β, γ (°)	96.221 (3), 111.320 (2), 111.736 (2)
V (Å³)	972.3 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.82
Crystal size (mm)	0.25 × 0.22 × 0.18

Data collection
Diffractometer	Bruker APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2000)
T_min, T_max	0.821, 0.866
No. of measured, independent and observed [I > 2σ(I)] reflections	7689, 3798, 3228
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.096, 1.05
No. of reflections	3798
No. of parameters	292
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.22

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O1ⁱ	0.85 (4)	1.79 (4)	2.602 (3)	159 (3)
O1W—H1WB···O4ⁱⁱ	0.80 (4)	1.94 (4)	2.740 (3)	172 (3)
O3—H3A···O6ⁱⁱⁱ	0.79 (4)	1.86 (4)	2.622 (3)	160 (4)

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

Acknowledgements

The authors thank the Program for Young Excellent Talents in Southeast University for financial support.

References

Bradshaw, D., Prior, T. J., Cussen, E. J., Claridge, J. B. & Rosseinsky, M. J. (2004). J. Am. Chem. Soc. 126, 6106–6114. Web of Science CSD CrossRef PubMed CAS Google Scholar
Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chui, S. S.-Y., Lo, S. M.-F., Charmant, J. P. H., Orpen, A. G. & Williams, I. D. (1999). Science, 283, 1148–1150. Web of Science CSD CrossRef PubMed CAS Google Scholar
Plater, M. J., Foreman, M. R. St J., Howie, R. A., Skakle, J. M. S., Coronado, E., Gomez-Garcia, C. J., Gelbrich, T. & Hursthouse, M. B. (2001). Inorg. Chim. Acta, 319, 159–175. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2000). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yang, J., Lu, N., Zhang, G., Cheng, L. & Gou, S.-H. (2008). Polyhedron, 27, 2119–2126. Web of Science CSD CrossRef CAS Google Scholar

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Volume 65| Part 1| January 2009| Page m14

doi:10.1107/S160053680804018X

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

catena-Poly[bis­­[(1,10-phenanthroline)iron(II)]-bis­­(μ-5-carb­oxy­benzene-1,3-di­carboxyl­ato)]

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

catena-Poly[bis[(1,10-phenanthroline)iron(II)]-bis(μ-5-carboxybenzene-1,3-dicarboxylato)]