μ-Aqua-bis­(μ-4-methyl­benzoato-κ2O:O′)bis­[(4-methyl­benzoato-κO)(1,10-phenanthroline-κ2N,N′)iron(II)]

Feng, S.

doi:10.1107/S1600536808014207

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Pages m817-m818

doi:10.1107/S1600536808014207

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μ-Aqua-bis(μ-4-methylbenzoato-κ²O:O′)bis[(4-methylbenzoato-κO)(1,10-phenanthroline-κ²N,N′)iron(II)]

Sun Feng ^a ^*

^aSchool of Chemistry and Environment, South China Normal University, Guangzhou 510006, People's Republic of China
^*Correspondence e-mail: fengsu60@yahoo.cn

(Received 11 April 2008; accepted 12 May 2008; online 17 May 2008)

In the title binuclear complex, [Fe₂(C₈H₇O₂)₄(C₁₂H₈N₂)₂(H₂O)], the Fe^II ion is six-coordinated by three carboxylate O atoms from three 4-methylbenzoate ligands, two N atoms from two 1,10-phenanthroline ligands and one bridging aqua ligand in a distorted octahedral geometry. The coordinated water molecule acting as the bridging ligand is located on a twofold axes and the complex molecule displays C₂ molecular symmetry. The Fe⋯Fe separation in the binuclear complex is 3.490 (3) Å. The crystal structure is stabilized by hydrogen bonding and π–π stacking interactions [the centroid–centroid distance between adjacent 1,10-phenanthroline ring systems is 3.653 (2) Å, and that between the 1,10-phenanthroline ring system and the phenyl ring of the 4-methylbenzoate unit of a neighbouring complex is 3.622 (3) Å].

Related literature

For related literature, see: Song et al. (2007 ).

Experimental

Crystal data

[Fe₂(C₈H₇O₂)₄(C₁₂H₈N₂)₂(H₂O)]
M_r = 1030.67
Monoclinic, C 2/c
a = 23.1987 (6) Å
b = 15.7222 (4) Å
c = 15.6464 (4) Å
β = 121.017 (1)°
V = 4890.8 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.66 mm⁻¹
T = 296 (2) K
0.20 × 0.19 × 0.16 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.880, T_max = 0.902
31900 measured reflections
5066 independent reflections
3725 reflections with I > 2σ(I)
R_int = 0.053

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.133
S = 1.05
5066 reflections
326 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Fe1—O3	2.1365 (18)
Fe1—O2ⁱ	2.1369 (18)
Fe1—O1	2.1657 (18)
Fe1—N1	2.275 (2)
Fe1—O1W	2.2970 (17)
Fe1—N2	2.298 (2)

O3—Fe1—O2ⁱ	93.91 (7)
O3—Fe1—O1	172.16 (8)
O2ⁱ—Fe1—O1	89.79 (7)
O3—Fe1—N1	100.73 (8)
O2ⁱ—Fe1—N1	86.60 (8)
O1—Fe1—N1	86.37 (7)
O3—Fe1—O1W	88.54 (6)
O2ⁱ—Fe1—O1W	108.77 (7)
O1—Fe1—O1W	83.73 (6)
N1—Fe1—O1W	161.62 (6)
O3—Fe1—N2	89.48 (8)
O2ⁱ—Fe1—N2	159.38 (8)
O1—Fe1—N2	89.47 (7)
N1—Fe1—N2	72.79 (8)
O1W—Fe1—N2	91.64 (7)
Symmetry code: (i) $[-x, y, -z+{\script{1\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W⋯O4ⁱ	0.938 (8)	1.80 (2)	2.578 (2)	138 (2)
Symmetry code: (i) $[-x, y, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808014207/kp2167sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808014207/kp2167Isup2.hkl

checkCIF report

Comment top

In the structural investigation of 4-methylbenzoate complexes, it has been found that the 4-methylbenzoic acid functions as a multidentate ligand [Song et al. (2007)] with versatile binding and coordination modes. In this report, an iron(II) complex, (I) (Fig. 1) was obtained by the reaction of 4-methylbenzoic acid, 1,10-phenanthroline and ferrous chloride in alkaline aqueous solution.

A half of the binuclear complex is an asymmetric unit where Fe^II ion is in the distorted octahedral geometry with the six coordinating atoms: three carboxyl O atoms from two µ₂-bridging 4-methylbenzoate ligands and one 4-methylbenzoate ligand, two N atoms from one chelating 1,10-phenanthroline ligands, and one µ₂-bridging aqua ligand. The Fe···Fe separation is 3.490 (3) Å. The crystal packing is via O—H···O hydrogen bond (Table 1) and via two π-π stacking interactions (Fig. 2). The centroid to centroid distance between adjacent 1,10-phenanthroline rings (x, –y,-1/2 + z) is 3.653 (2) Å, whereas the centroid to centroid distance between 1,10-phenanthroline ring and phenyl ring of 4-methylbenzoate of neighbouring complexes (1/2 - x, 1/2 - y, 1 - z) is 3.622 (3) Å.

Related literature top

For related literature, see: Song et al. (2007).

Experimental top

A mixture of ferrous chloride (1 mmol), 4-methylbenzate (1 mmol), 1,10-phenanthroline (1 mmol), NaOH (1.5 mmol) and H₂O (12 mL) was placed in a 23 mL Teflon reactor, which was heated to 433 K for three days and then cooled to room temperature at a rate of 10 K h^-1. The crystals obtained were washed with water and dryed in air.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The structure of (I) showing the atomic numbering scheme. Non-H atoms are shown with the 30% probability displacement ellipsoids. Unlabelled atoms are related to the labelled atoms by the symmetry code (-x, y, 1/2 - z).
	Fig. 2. A packing view of the title compound.

µ-Aqua-bis(µ-4-methylbenzoato-κ²O:O')bis[(4-methylbenzoato- κO)(1,10-phenanthroline-κ²N,N')iron(II)] top

Crystal data top

[Fe₂(C₈H₇O₂)₄(C₁₂H₈N₂)₂(H₂O)]	F(000) = 2136
M_r = 1030.67	D_x = 1.400 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5300 reflections
a = 23.1987 (6) Å	θ = 1.3–28.0°
b = 15.7222 (4) Å	µ = 0.66 mm⁻¹
c = 15.6464 (4) Å	T = 296 K
β = 121.017 (1)°	Block, colourless
V = 4890.8 (2) Å³	0.20 × 0.19 × 0.16 mm
Z = 4

Data collection top

Bruker APEXII area-detector diffractometer	5066 independent reflections
Radiation source: fine-focus sealed tube	3725 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.053
ϕ and ω scans	θ_max = 26.5°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −29→29
T_min = 0.880, T_max = 0.902	k = −19→19
31900 measured reflections	l = −19→19

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0679P)² + 3.2244P] where P = (F_o² + 2F_c²)/3
5066 reflections	(Δ/σ)_max = 0.002
326 parameters	Δρ_max = 0.30 e Å⁻³
2 restraints	Δρ_min = −0.42 e Å⁻³

Crystal data top

[Fe₂(C₈H₇O₂)₄(C₁₂H₈N₂)₂(H₂O)]	V = 4890.8 (2) Å³
M_r = 1030.67	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 23.1987 (6) Å	µ = 0.66 mm⁻¹
b = 15.7222 (4) Å	T = 296 K
c = 15.6464 (4) Å	0.20 × 0.19 × 0.16 mm
β = 121.017 (1)°

Data collection top

Bruker APEXII area-detector diffractometer	5066 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3725 reflections with I > 2σ(I)
T_min = 0.880, T_max = 0.902	R_int = 0.053
31900 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	2 restraints
wR(F²) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.30 e Å⁻³
5066 reflections	Δρ_min = −0.42 e Å⁻³
326 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	0.041139 (18)	0.35596 (2)	0.37994 (3)	0.03908 (15)
C1	0.10393 (16)	0.51103 (18)	0.5379 (2)	0.0495 (7)
H1	0.0624	0.5365	0.4966	0.059*
C2	0.15332 (18)	0.5574 (2)	0.6182 (2)	0.0612 (9)
H2	0.1447	0.6126	0.6302	0.073*
C3	0.21397 (18)	0.5211 (2)	0.6784 (2)	0.0664 (10)
H3	0.2474	0.5515	0.7321	0.080*
C4	0.22666 (15)	0.4382 (2)	0.6603 (2)	0.0545 (8)
C5	0.28939 (16)	0.3946 (3)	0.7205 (2)	0.0717 (11)
H5	0.3250	0.4229	0.7738	0.086*
C6	0.29761 (16)	0.3135 (3)	0.7014 (2)	0.0691 (10)
H6	0.3389	0.2871	0.7417	0.083*
C7	0.24490 (14)	0.2671 (2)	0.6211 (2)	0.0543 (8)
C8	0.25042 (16)	0.1818 (2)	0.5991 (3)	0.0636 (9)
H8	0.2905	0.1524	0.6380	0.076*
C9	0.19760 (17)	0.1427 (2)	0.5217 (3)	0.0624 (9)
H9	0.2003	0.0855	0.5086	0.075*
C10	0.13890 (15)	0.18871 (19)	0.4614 (2)	0.0523 (7)
H10	0.1034	0.1616	0.4068	0.063*
C11	0.18322 (13)	0.30873 (18)	0.55822 (19)	0.0432 (6)
C12	0.17422 (13)	0.39593 (18)	0.57830 (19)	0.0414 (6)
C13	0.07480 (12)	0.46759 (16)	0.25133 (19)	0.0360 (6)
C14	0.11705 (13)	0.54627 (16)	0.28046 (19)	0.0384 (6)
C15	0.17772 (14)	0.54973 (19)	0.3703 (2)	0.0507 (7)
H15	0.1911	0.5041	0.4143	0.061*
C16	0.21825 (16)	0.6204 (2)	0.3949 (3)	0.0636 (9)
H16	0.2594	0.6209	0.4545	0.076*
C17	0.19931 (19)	0.6901 (2)	0.3334 (3)	0.0633 (9)
C18	0.13827 (19)	0.68755 (19)	0.2446 (3)	0.0609 (9)
H18	0.1245	0.7344	0.2023	0.073*
C19	0.09739 (15)	0.61659 (17)	0.2176 (2)	0.0462 (6)
H19	0.0567	0.6158	0.1572	0.055*
C20	0.2436 (2)	0.7685 (3)	0.3605 (4)	0.1012 (16)
H20A	0.2891	0.7538	0.4097	0.152*
H20B	0.2276	0.8114	0.3869	0.152*
H20C	0.2422	0.7900	0.3020	0.152*
C21	−0.03260 (13)	0.21381 (18)	0.4188 (2)	0.0419 (6)
C22	−0.04954 (13)	0.17394 (19)	0.4901 (2)	0.0441 (6)
C23	−0.05669 (16)	0.2209 (2)	0.5580 (2)	0.0582 (8)
H23	−0.0504	0.2795	0.5608	0.070*
C24	−0.07324 (18)	0.1821 (3)	0.6230 (3)	0.0715 (10)
H24	−0.0791	0.2152	0.6672	0.086*
C25	−0.08085 (18)	0.0948 (3)	0.6218 (3)	0.0680 (9)
C26	−0.07224 (18)	0.0482 (2)	0.5554 (3)	0.0677 (9)
H26	−0.0761	−0.0107	0.5550	0.081*
C27	−0.05788 (15)	0.08647 (19)	0.4887 (2)	0.0545 (8)
H27	−0.0538	0.0534	0.4428	0.065*
C28	−0.0974 (2)	0.0524 (3)	0.6938 (3)	0.1022 (15)
H28A	−0.0868	0.0904	0.7480	0.153*
H28B	−0.0714	0.0012	0.7194	0.153*
H28C	−0.1444	0.0387	0.6596	0.153*
N1	0.11349 (11)	0.43230 (14)	0.51775 (15)	0.0415 (5)
N2	0.13141 (10)	0.26953 (14)	0.47845 (16)	0.0411 (5)
O1	0.09509 (9)	0.40711 (12)	0.31245 (14)	0.0455 (5)
O2	0.02203 (9)	0.46592 (11)	0.16733 (14)	0.0449 (5)
O3	−0.01572 (10)	0.29140 (12)	0.43251 (15)	0.0517 (5)
O4	−0.03673 (11)	0.16889 (14)	0.35009 (15)	0.0555 (5)
O1W	0.0000	0.26095 (16)	0.2500	0.0398 (6)
H1W	0.0291 (12)	0.2479 (17)	0.227 (2)	0.060*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.0366 (2)	0.0383 (2)	0.0366 (2)	0.00068 (15)	0.01482 (18)	0.00227 (16)
C1	0.0582 (18)	0.0447 (16)	0.0424 (15)	−0.0101 (14)	0.0236 (14)	−0.0025 (13)
C2	0.082 (2)	0.0510 (19)	0.0527 (18)	−0.0247 (17)	0.0359 (19)	−0.0115 (15)
C3	0.068 (2)	0.077 (2)	0.0430 (17)	−0.0399 (19)	0.0213 (17)	−0.0120 (17)
C4	0.0486 (17)	0.071 (2)	0.0358 (15)	−0.0213 (15)	0.0159 (14)	0.0032 (14)
C5	0.0423 (18)	0.105 (3)	0.0417 (18)	−0.0271 (19)	0.0026 (15)	0.0093 (19)
C6	0.0330 (16)	0.102 (3)	0.0511 (19)	−0.0008 (18)	0.0061 (15)	0.023 (2)
C7	0.0357 (15)	0.076 (2)	0.0480 (17)	0.0066 (14)	0.0190 (14)	0.0223 (15)
C8	0.0464 (18)	0.080 (2)	0.066 (2)	0.0248 (17)	0.0302 (18)	0.0348 (19)
C9	0.056 (2)	0.057 (2)	0.074 (2)	0.0179 (16)	0.0329 (19)	0.0174 (17)
C10	0.0472 (17)	0.0490 (17)	0.0554 (18)	0.0086 (13)	0.0226 (15)	0.0087 (14)
C11	0.0321 (13)	0.0574 (18)	0.0361 (14)	0.0012 (12)	0.0147 (12)	0.0144 (12)
C12	0.0354 (14)	0.0525 (16)	0.0314 (13)	−0.0105 (12)	0.0137 (12)	0.0046 (12)
C13	0.0333 (13)	0.0368 (14)	0.0404 (14)	−0.0016 (11)	0.0208 (12)	−0.0015 (11)
C14	0.0386 (14)	0.0401 (14)	0.0368 (14)	−0.0034 (11)	0.0197 (12)	−0.0051 (11)
C15	0.0429 (16)	0.0550 (18)	0.0469 (16)	−0.0032 (13)	0.0180 (14)	−0.0038 (14)
C16	0.0505 (19)	0.072 (2)	0.061 (2)	−0.0193 (17)	0.0235 (16)	−0.0280 (18)
C17	0.075 (2)	0.057 (2)	0.074 (2)	−0.0326 (17)	0.050 (2)	−0.0351 (18)
C18	0.093 (3)	0.0361 (16)	0.075 (2)	−0.0073 (16)	0.058 (2)	−0.0052 (15)
C19	0.0534 (17)	0.0385 (14)	0.0468 (16)	−0.0029 (13)	0.0259 (14)	−0.0041 (12)
C20	0.131 (4)	0.081 (3)	0.124 (4)	−0.067 (3)	0.089 (3)	−0.058 (3)
C21	0.0306 (13)	0.0470 (16)	0.0458 (15)	0.0021 (11)	0.0180 (12)	0.0079 (13)
C22	0.0338 (14)	0.0513 (16)	0.0443 (15)	−0.0009 (12)	0.0181 (13)	0.0071 (13)
C23	0.065 (2)	0.0578 (19)	0.0601 (19)	−0.0069 (16)	0.0380 (17)	0.0005 (16)
C24	0.079 (2)	0.087 (3)	0.066 (2)	−0.008 (2)	0.049 (2)	−0.0042 (19)
C25	0.065 (2)	0.085 (3)	0.061 (2)	−0.0109 (19)	0.0369 (18)	0.0139 (19)
C26	0.075 (2)	0.057 (2)	0.074 (2)	−0.0110 (17)	0.041 (2)	0.0135 (18)
C27	0.0579 (19)	0.0508 (18)	0.0568 (18)	−0.0047 (14)	0.0311 (16)	0.0045 (14)
C28	0.109 (3)	0.126 (4)	0.093 (3)	−0.022 (3)	0.068 (3)	0.025 (3)
N1	0.0429 (13)	0.0426 (13)	0.0329 (11)	−0.0052 (10)	0.0152 (10)	0.0019 (10)
N2	0.0356 (12)	0.0418 (12)	0.0402 (12)	0.0033 (10)	0.0155 (10)	0.0072 (10)
O1	0.0432 (11)	0.0407 (11)	0.0543 (12)	0.0012 (8)	0.0263 (9)	0.0097 (9)
O2	0.0400 (10)	0.0427 (11)	0.0442 (11)	−0.0085 (8)	0.0162 (9)	−0.0041 (8)
O3	0.0583 (12)	0.0442 (11)	0.0649 (13)	−0.0038 (9)	0.0406 (11)	0.0047 (9)
O4	0.0634 (13)	0.0565 (12)	0.0519 (12)	−0.0118 (10)	0.0334 (11)	−0.0035 (10)
O1W	0.0425 (15)	0.0403 (14)	0.0374 (14)	0.000	0.0211 (12)	0.000

Geometric parameters (Å, º) top

Fe1—O3	2.1365 (18)	C14—C19	1.391 (4)
Fe1—O2ⁱ	2.1369 (18)	C15—C16	1.376 (4)
Fe1—O1	2.1657 (18)	C15—H15	0.9300
Fe1—N1	2.275 (2)	C16—C17	1.373 (5)
Fe1—O1W	2.2970 (17)	C16—H16	0.9300
Fe1—N2	2.298 (2)	C17—C18	1.382 (5)
C1—N1	1.324 (4)	C17—C20	1.519 (4)
C1—C2	1.393 (4)	C18—C19	1.382 (4)
C1—H1	0.9300	C18—H18	0.9300
C2—C3	1.352 (5)	C19—H19	0.9300
C2—H2	0.9300	C20—H20A	0.9600
C3—C4	1.398 (5)	C20—H20B	0.9600
C3—H3	0.9300	C20—H20C	0.9600
C4—C12	1.400 (4)	C21—O4	1.248 (3)
C4—C5	1.436 (5)	C21—O3	1.265 (3)
C5—C6	1.346 (5)	C21—C22	1.499 (4)
C5—H5	0.9300	C22—C23	1.372 (4)
C6—C7	1.422 (5)	C22—C27	1.387 (4)
C6—H6	0.9300	C23—C24	1.398 (4)
C7—C8	1.406 (5)	C23—H23	0.9300
C7—C11	1.412 (4)	C24—C25	1.383 (5)
C8—C9	1.349 (5)	C24—H24	0.9300
C8—H8	0.9300	C25—C26	1.367 (5)
C9—C10	1.395 (4)	C25—C28	1.519 (5)
C9—H9	0.9300	C26—C27	1.387 (4)
C10—N2	1.328 (4)	C26—H26	0.9300
C10—H10	0.9300	C27—H27	0.9300
C11—N2	1.355 (3)	C28—H28A	0.9600
C11—C12	1.446 (4)	C28—H28B	0.9600
C12—N1	1.354 (3)	C28—H28C	0.9600
C13—O2	1.252 (3)	O2—Fe1ⁱ	2.1369 (18)
C13—O1	1.256 (3)	O1W—Fe1ⁱ	2.2970 (17)
C13—C14	1.496 (3)	O1W—H1W	0.938 (8)
C14—C15	1.386 (4)

O3—Fe1—O2ⁱ	93.91 (7)	C14—C15—H15	119.8
O3—Fe1—O1	172.16 (8)	C17—C16—C15	121.6 (3)
O2ⁱ—Fe1—O1	89.79 (7)	C17—C16—H16	119.2
O3—Fe1—N1	100.73 (8)	C15—C16—H16	119.2
O2ⁱ—Fe1—N1	86.60 (8)	C16—C17—C18	118.3 (3)
O1—Fe1—N1	86.37 (7)	C16—C17—C20	121.8 (4)
O3—Fe1—O1W	88.54 (6)	C18—C17—C20	120.0 (4)
O2ⁱ—Fe1—O1W	108.77 (7)	C19—C18—C17	121.2 (3)
O1—Fe1—O1W	83.73 (6)	C19—C18—H18	119.4
N1—Fe1—O1W	161.62 (6)	C17—C18—H18	119.4
O3—Fe1—N2	89.48 (8)	C18—C19—C14	120.1 (3)
O2ⁱ—Fe1—N2	159.38 (8)	C18—C19—H19	119.9
O1—Fe1—N2	89.47 (7)	C14—C19—H19	119.9
N1—Fe1—N2	72.79 (8)	C17—C20—H20A	109.5
O1W—Fe1—N2	91.64 (7)	C17—C20—H20B	109.5
N1—C1—C2	122.9 (3)	H20A—C20—H20B	109.5
N1—C1—H1	118.5	C17—C20—H20C	109.5
C2—C1—H1	118.5	H20A—C20—H20C	109.5
C3—C2—C1	119.0 (3)	H20B—C20—H20C	109.5
C3—C2—H2	120.5	O4—C21—O3	124.9 (3)
C1—C2—H2	120.5	O4—C21—C22	118.1 (3)
C2—C3—C4	120.3 (3)	O3—C21—C22	117.0 (3)
C2—C3—H3	119.8	C23—C22—C27	118.4 (3)
C4—C3—H3	119.8	C23—C22—C21	122.3 (3)
C3—C4—C12	117.0 (3)	C27—C22—C21	119.4 (3)
C3—C4—C5	124.1 (3)	C22—C23—C24	121.0 (3)
C12—C4—C5	118.9 (3)	C22—C23—H23	119.5
C6—C5—C4	121.2 (3)	C24—C23—H23	119.5
C6—C5—H5	119.4	C25—C24—C23	120.3 (3)
C4—C5—H5	119.4	C25—C24—H24	119.8
C5—C6—C7	121.8 (3)	C23—C24—H24	119.8
C5—C6—H6	119.1	C26—C25—C24	118.3 (3)
C7—C6—H6	119.1	C26—C25—C28	121.3 (4)
C8—C7—C11	117.3 (3)	C24—C25—C28	120.4 (4)
C8—C7—C6	124.0 (3)	C25—C26—C27	121.7 (3)
C11—C7—C6	118.6 (3)	C25—C26—H26	119.2
C9—C8—C7	120.0 (3)	C27—C26—H26	119.2
C9—C8—H8	120.0	C26—C27—C22	120.2 (3)
C7—C8—H8	120.0	C26—C27—H27	119.9
C8—C9—C10	119.3 (3)	C22—C27—H27	119.9
C8—C9—H9	120.4	C25—C28—H28A	109.5
C10—C9—H9	120.4	C25—C28—H28B	109.5
N2—C10—C9	123.0 (3)	H28A—C28—H28B	109.5
N2—C10—H10	118.5	C25—C28—H28C	109.5
C9—C10—H10	118.5	H28A—C28—H28C	109.5
N2—C11—C7	122.0 (3)	H28B—C28—H28C	109.5
N2—C11—C12	118.2 (2)	C1—N1—C12	118.0 (2)
C7—C11—C12	119.8 (3)	C1—N1—Fe1	125.91 (19)
N1—C12—C4	122.7 (3)	C12—N1—Fe1	115.70 (18)
N1—C12—C11	117.6 (2)	C10—N2—C11	118.3 (2)
C4—C12—C11	119.6 (3)	C10—N2—Fe1	126.82 (19)
O2—C13—O1	124.3 (2)	C11—N2—Fe1	114.71 (17)
O2—C13—C14	118.0 (2)	C13—O1—Fe1	124.66 (16)
O1—C13—C14	117.7 (2)	C13—O2—Fe1ⁱ	120.36 (16)
C15—C14—C19	118.5 (3)	C21—O3—Fe1	126.24 (18)
C15—C14—C13	120.3 (2)	Fe1—O1W—Fe1ⁱ	98.87 (10)
C19—C14—C13	121.1 (2)	Fe1—O1W—H1W	115.5 (18)
C16—C15—C14	120.3 (3)	Fe1ⁱ—O1W—H1W	81.6 (18)
C16—C15—H15	119.8

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O4ⁱ	0.94 (1)	1.80 (2)	2.578 (2)	138 (2)

Symmetry code: (i) −x, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Fe₂(C₈H₇O₂)₄(C₁₂H₈N₂)₂(H₂O)]
M_r	1030.67
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	23.1987 (6), 15.7222 (4), 15.6464 (4)
β (°)	121.017 (1)
V (Å³)	4890.8 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.66
Crystal size (mm)	0.20 × 0.19 × 0.16

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.880, 0.902
No. of measured, independent and observed [I > 2σ(I)] reflections	31900, 5066, 3725
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.133, 1.06
No. of reflections	5066
No. of parameters	326
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.42

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Fe1—O3	2.1365 (18)	Fe1—N1	2.275 (2)
Fe1—O2ⁱ	2.1369 (18)	Fe1—O1W	2.2970 (17)
Fe1—O1	2.1657 (18)	Fe1—N2	2.298 (2)

O3—Fe1—O2ⁱ	93.91 (7)	O1—Fe1—O1W	83.73 (6)
O3—Fe1—O1	172.16 (8)	N1—Fe1—O1W	161.62 (6)
O2ⁱ—Fe1—O1	89.79 (7)	O3—Fe1—N2	89.48 (8)
O3—Fe1—N1	100.73 (8)	O2ⁱ—Fe1—N2	159.38 (8)
O2ⁱ—Fe1—N1	86.60 (8)	O1—Fe1—N2	89.47 (7)
O1—Fe1—N1	86.37 (7)	N1—Fe1—N2	72.79 (8)
O3—Fe1—O1W	88.54 (6)	O1W—Fe1—N2	91.64 (7)
O2ⁱ—Fe1—O1W	108.77 (7)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O4ⁱ	0.938 (8)	1.80 (2)	2.578 (2)	138 (2)

Symmetry code: (i) −x, y, −z+1/2.

Acknowledgements

The author acknowledges South China Normal University for supporting this work.

References

Bruker (2004). APEX2 and SMART. Bruker AXS Inc, Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (1996). 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
Song, W.-D., Gu, C.-S., Hao, X.-M. & Liu, J.-W. (2007). Acta Cryst. E63, m1023–m1024. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar

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Volume 64| Part 6| June 2008| Pages m817-m818

doi:10.1107/S1600536808014207

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