catena-Poly[bis-[(1,10-phenanthroline)iron(II)]-bis-(μ-5-carboxy-benzene-1,3-dicarboxyl-ato)].

The asymmetric unit of the title compound, [Fe(C(9)H(4)O(6))(C(12)H(8)N(2))(H(2)O)](n), contains one Fe(II) cation, one 5-carboxy-benzene-1,3-dicarboxyl-ate dianion (Hbtc), one 1,10-phenanthroline (phen) ligand and one water mol-ecule. The Fe(II) centre displays a distorted octa-hedral geometry, being surrounded by one phen ligand, two μ(2)-O atoms of two carboxyl-ate groups from two Hbtc ligands, one O atom from one carboxyl-ate of another Hbtc ligand and one terminal water mol-ecule. One carboxyl-ate group ligates two Fe(II) cations in a μ(1,1) mode, while the other carboxyl-ate 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 = 462.19

Triclinic,

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[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.096

S = 1.05

3798 reflections

292 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.22 e Å−3

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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Fe(C9H4O6)(C12H8N2)(H2O)]	Z = 2
Mr = 462.19	F(000) = 472
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0467P)2 + 0.209P] where P = (Fo2 + 2Fc2)/3
3798 reflections	(Δ/σ)max < 0.001
292 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)*

	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)

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)

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···O6iv	0.79 (4)	1.86 (4)	2.622 (3)	160 (4)

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) ; (ii) ; (iii) .