Tetra­aqua­(2,2′-bipyridine-5,5′-dicarboxyl­ato)iron(II) dihydrate

In the title compound, [Fe(C₁₂H₆N₂O₄)(H₂O)₄]·2H₂O, the Fe^II ion (site symmetry 2) is bonded to one N,N′-bidentate 2,2′-bipyridine-5,5′-dicarboxyl­ate ligand and four water mol­ecules, resulting in a distorted cis-FeN₂O₄ coordination geometry. A network of π–π inter­actions and O—H...O hydrogen bonds gives rise to a robust supra­molecular network in the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.039
• wR factor = 0.085
• Data-to-parameter ratio = 13.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT417_ALERT_2_C Short Inter D-H..H-D       H1B    ..  H3B     ..       2.14 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SHELXTL (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Tetraaqua(2,2'-bipyridine-5,5'-dicarboxylato)iron(II) dihydrate

Crystal data

[Fe(C12H6N2O4)(H2O)4]·2H2O	F(000) = 840
Mr = 406.13	Dx = 1.730 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3035 reflections
a = 12.7597 (11) Å	θ = 2.7–28.3°
b = 9.2615 (8) Å	µ = 1.03 mm^−1
c = 13.2195 (11) Å	T = 173 K
β = 93.620 (2)°	Prism, red
V = 1559.1 (2) Å^3	0.30 × 0.15 × 0.12 mm
Z = 4

Data collection

Siemens SMART CCD diffractometer	1827 independent reflections
Radiation source: fine-focus sealed tube	1666 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
ω scans	θmax = 28.3°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→16
Tmin = 0.777, Tmax = 0.884	k = −12→8
4812 measured reflections	l = −15→17

Refinement

Refinement on F^2	Primary atom site location: heavy-atom method
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.085	H atoms treated by a mixture of independent and constrained refinement
S = 1.19	w = 1/[σ^2(Fo^2) + (0.0294P)^2 + 2.755P] where P = (Fo^2 + 2Fc^2)/3
1827 reflections	(Δ/σ)max < 0.001
138 parameters	Δρmax = 0.52 e Å^−3
0 restraints	Δρmin = −0.79 e Å^−3

Special details

Experimental. IR (KBr pellet, cm^-1): 3390, 2940, 1600, 1500, 1360, 1230, 770.

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 (Ų)

	x	y	z	Uiso*/Ueq
Fe1	0.0000	0.69530 (5)	0.2500	0.01321 (13)
O1	0.25315 (12)	1.08141 (18)	0.61965 (12)	0.0221 (4)
O2	0.20853 (13)	0.84945 (18)	0.62409 (12)	0.0232 (4)
O1W	−0.04583 (15)	0.5442 (2)	0.14090 (15)	0.0279 (4)
H1A	−0.100 (3)	0.504 (4)	0.138 (2)	0.041 (10)*
H1B	−0.006 (3)	0.494 (4)	0.123 (2)	0.035 (10)*
O2W	−0.16387 (12)	0.6825 (2)	0.29257 (13)	0.0190 (3)
H2A	−0.205 (3)	0.670 (3)	0.241 (3)	0.039 (9)*
H2B	−0.184 (3)	0.748 (4)	0.320 (3)	0.047 (11)*
O3W	0.13099 (15)	0.4237 (2)	0.09342 (17)	0.0366 (5)
H3A	0.153 (3)	0.340 (5)	0.120 (3)	0.076 (14)*
H3B	0.162 (3)	0.480 (5)	0.132 (3)	0.066 (13)*
N1	0.04329 (13)	0.8811 (2)	0.34370 (13)	0.0148 (4)
C1	0.09674 (16)	0.8717 (2)	0.43480 (15)	0.0157 (4)
H1	0.1059	0.7793	0.4653	0.019*
C2	0.13880 (15)	0.9911 (2)	0.48570 (15)	0.0146 (4)
C3	0.12427 (17)	1.1260 (2)	0.44117 (16)	0.0170 (4)
H3	0.1522	1.2100	0.4741	0.020*
C4	0.06813 (17)	1.1367 (2)	0.34745 (16)	0.0175 (4)
H4	0.0568	1.2282	0.3162	0.021*
C5	0.02926 (15)	1.0129 (2)	0.30055 (15)	0.0142 (4)
C6	0.20443 (16)	0.9727 (2)	0.58463 (16)	0.0159 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.0120 (2)	0.0127 (2)	0.0145 (2)	0.000	−0.00342 (15)	0.000
O1	0.0206 (8)	0.0206 (9)	0.0239 (8)	0.0024 (7)	−0.0091 (7)	−0.0049 (7)
O2	0.0246 (9)	0.0231 (9)	0.0208 (8)	−0.0007 (7)	−0.0074 (7)	0.0033 (7)
O1W	0.0166 (9)	0.0252 (10)	0.0408 (11)	0.0020 (8)	−0.0056 (8)	−0.0159 (8)
O2W	0.0150 (8)	0.0226 (9)	0.0190 (8)	0.0023 (7)	−0.0023 (6)	−0.0035 (7)
O3W	0.0264 (10)	0.0310 (12)	0.0518 (13)	0.0051 (9)	−0.0024 (9)	−0.0174 (10)
N1	0.0132 (8)	0.0170 (9)	0.0137 (8)	0.0009 (7)	−0.0024 (7)	0.0015 (7)
C1	0.0134 (9)	0.0181 (11)	0.0153 (10)	0.0033 (8)	−0.0015 (8)	0.0025 (8)
C2	0.0096 (9)	0.0204 (11)	0.0135 (9)	0.0006 (8)	−0.0004 (7)	−0.0013 (8)
C3	0.0153 (10)	0.0181 (11)	0.0172 (10)	−0.0018 (8)	−0.0018 (8)	−0.0024 (8)
C4	0.0177 (10)	0.0165 (11)	0.0179 (10)	−0.0005 (9)	−0.0026 (8)	0.0009 (8)
C5	0.0106 (9)	0.0181 (11)	0.0136 (10)	0.0009 (8)	−0.0007 (8)	−0.0006 (8)
C6	0.0122 (9)	0.0206 (11)	0.0146 (10)	0.0037 (8)	−0.0014 (8)	−0.0026 (8)

Geometric parameters (Å, º)

Fe1—N1	2.1709 (19)	O3W—H3B	0.82 (4)
Fe1—N1^i	2.1709 (18)	N1—C1	1.349 (3)
Fe1—O1W	2.0671 (18)	N1—C5	1.355 (3)
Fe1—O1W^i	2.0671 (18)	C1—C2	1.385 (3)
Fe1—O2W	2.2026 (16)	C1—H1	0.9500
Fe1—O2W^i	2.2026 (16)	C2—C3	1.389 (3)
C6—O1	1.256 (3)	C2—C6	1.517 (3)
C6—O2	1.255 (3)	C3—C4	1.395 (3)
O1W—H1A	0.79 (3)	C3—H3	0.9500
O1W—H1B	0.74 (3)	C4—C5	1.381 (3)
O2W—H2A	0.84 (3)	C4—H4	0.9500
O2W—H2B	0.76 (4)	C5—C5^i	1.489 (4)
O3W—H3A	0.88 (5)
O1W—Fe1—N1	170.08 (8)	C1—N1—C5	118.68 (18)
O1W—Fe1—O2W	84.87 (8)	C1—N1—Fe1	123.68 (15)
N1—Fe1—O2W	96.22 (7)	C5—N1—Fe1	116.86 (13)
O1W—Fe1—O1W^i	94.81 (12)	N1—C1—C2	122.8 (2)
O1W^i—Fe1—N1	95.03 (7)	N1—C1—H1	118.6
O1W—Fe1—N1^i	95.03 (7)	C2—C1—H1	118.6
O1W^i—Fe1—N1^i	170.08 (8)	C1—C2—C3	118.37 (19)
N1—Fe1—N1^i	75.17 (9)	C1—C2—C6	120.35 (19)
O1W—Fe1—O2W^i	90.95 (7)	C3—C2—C6	121.18 (19)
O1W^i—Fe1—O2W^i	84.87 (8)	C2—C3—C4	119.2 (2)
N1—Fe1—O2W^i	88.68 (6)	C2—C3—H3	120.4
N1^i—Fe1—O2W^i	96.22 (7)	C4—C3—H3	120.4
O1W^i—Fe1—O2W	90.95 (7)	C5—C4—C3	119.3 (2)
N1^i—Fe1—O2W	88.68 (6)	C5—C4—H4	120.3
O2W^i—Fe1—O2W	173.83 (10)	C3—C4—H4	120.3
Fe1—O1W—H1A	125 (2)	N1—C5—C4	121.67 (18)
Fe1—O1W—H1B	119 (2)	N1—C5—C5^i	115.05 (11)
H1A—O1W—H1B	108 (4)	C4—C5—C5^i	123.27 (13)
Fe1—O2W—H2A	110 (2)	O1—C6—O2	124.69 (19)
Fe1—O2W—H2B	115 (3)	O1—C6—C2	117.5 (2)
H2A—O2W—H2B	107 (3)	O2—C6—C2	117.80 (19)
H3A—O3W—H3B	100 (4)
O1W^i—Fe1—N1—C1	8.45 (17)	C6—C2—C3—C4	176.51 (19)
N1^i—Fe1—N1—C1	−173.1 (2)	C2—C3—C4—C5	−0.7 (3)
O2W^i—Fe1—N1—C1	−76.28 (17)	C1—N1—C5—C4	0.0 (3)
O2W—Fe1—N1—C1	99.96 (17)	Fe1—N1—C5—C4	−170.29 (16)
O1W^i—Fe1—N1—C5	178.18 (16)	C1—N1—C5—C5^i	179.2 (2)
N1^i—Fe1—N1—C5	−3.34 (11)	Fe1—N1—C5—C5^i	8.9 (3)
O2W^i—Fe1—N1—C5	93.45 (15)	C3—C4—C5—N1	0.7 (3)
O2W—Fe1—N1—C5	−90.31 (15)	C3—C4—C5—C5^i	−178.5 (2)
C5—N1—C1—C2	−0.6 (3)	C1—C2—C6—O2	−8.3 (3)
Fe1—N1—C1—C2	168.92 (16)	C3—C2—C6—O2	175.3 (2)
N1—C1—C2—C3	0.6 (3)	C1—C2—C6—O1	169.8 (2)
N1—C1—C2—C6	−175.87 (19)	C3—C2—C6—O1	−6.6 (3)
C1—C2—C3—C4	0.1 (3)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1A···O1^ii	0.79 (3)	2.03 (4)	2.815 (3)	173 (3)
O1W—H1B···O3W	0.74 (3)	1.93 (4)	2.629 (3)	158 (3)
O2W—H2A···O2^ii	0.84 (3)	1.85 (4)	2.691 (2)	177 (3)
O2W—H2B···O1^iii	0.76 (4)	2.00 (4)	2.755 (3)	172 (4)
O3W—H3A···O2^iv	0.88 (5)	1.89 (5)	2.737 (3)	159 (4)
O3W—H3B···O2W^i	0.82 (4)	2.12 (4)	2.848 (3)	148 (4)
C1—H1···O3W^v	0.95	2.54	3.458 (3)	163

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