Aqua­(picolinato N-oxide-κ2O1,O2)(pyridine-2,6-dicarboxyl­ato-κ3O,N,O′)iron(III) monohydrate

Han, D.; Wang, D.

doi:10.1107/S1600536808030663

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page m1343

doi:10.1107/S1600536808030663

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Aqua(picolinato N-oxide-κ²O¹,O²)(pyridine-2,6-dicarboxylato-κ³O,N,O′)iron(III) monohydrate

Dongdong Han ^a ^* and Dong'e Wang ^b

^aManagement Department of Zhejiang Pharmaceutical College, Ningbo, Zhejiang 315100, People's Republic of China, and ^bDepartment of Chemistry, Kashgar Teachers College, Kashgar, Xinjiang 844000, People's Republic of China
^*Correspondence e-mail: ch20050620@163.com

(Received 31 August 2008; accepted 23 September 2008; online 27 September 2008)

In the title compound, [Fe(C₆H₄NO₃)(C₇H₃NO₄)(H₂O)]·H₂O, the Fe^III ion is coordinated by two O and one N atoms from a pyridine-2,6-dicarboxylate ligand, by two O atoms from a picolinate N-oxide ligand and by one water O atom in a distorted octahedral geometry [Fe—O = 1.940 (3)–2.033 (3) Å and Fe—N = 2.057 (4) Å]. In the crystal structure, the coordinated and solvent water molecules contribute to the formation of O—H⋯O hydrogen bonds, which link the molecules into layers parallel to the ab plane.

Related literature

For related crystal structures, see: Lainé et al. (1995 ); Wu et al. (2007 ).

Experimental

Crystal data

[Fe(C₆H₄NO₃)(C₇H₃NO₄)(H₂O)]·H₂O
M_r = 395.09
Triclinic, $[P \overline 1]$
a = 6.6023 (13) Å
b = 7.7256 (16) Å
c = 15.520 (3) Å
α = 102.585 (4)°
β = 95.801 (4)°
γ = 105.743 (4)°
V = 732.7 (3) Å³
Z = 2
Mo Kα radiation
μ = 1.09 mm⁻¹
T = 293 (2) K
0.16 × 0.14 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ) T_min = 0.84, T_max = 0.87
3915 measured reflections
2749 independent reflections
1667 reflections with I > 2σ(I)
R_int = 0.047

Refinement

R[F² > 2σ(F²)] = 0.060
wR(F²) = 0.096
S = 0.85
2749 reflections
238 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O8—H8A⋯O2ⁱ	0.85 (4)	1.81 (4)	2.637 (5)	164 (4)
O8—H8B⋯O9ⁱⁱ	0.83 (3)	1.79 (4)	2.571 (5)	157 (5)
O9—H9A⋯O3ⁱⁱⁱ	0.87 (5)	1.88 (5)	2.730 (5)	167 (5)
O9—H9B⋯O5	0.86 (5)	1.97 (6)	2.821 (5)	173 (4)
Symmetry codes: (i) x+1, y, z; (ii) x, y-1, z; (iii) x-1, y, z.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; 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/S1600536808030663/cv2445sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808030663/cv2445Isup2.hkl

checkCIF report

Comment top

Recently, the 2D zinc(II) and 1D copper(II) complexes with pyridine-2,6-dicarboxylic acid N-oxide and dicarboxylato ligands were reported by Wu et al. (2007). As a contribution to this area, we report the crystal structure of the title compound, (I).

In (I) (Fig. 1), the Fe^III ion is coordinated by two O and one N atoms from pyridine-2,6-dicarboxylato ligand, two O atoms from picolinato-N-oxide ligand, and one water molecule in a distorted octahedral geometry. Atoms O1, O4, O7 and N1 lie in equatorial plane, with the O1—N1—O4—O7 torsion angle of 1.94 (15)°, while Fe1 deviates from the equatorial plane at 0.057 Å. Atoms O5 and O8 occupy the axial sites with the angle O5—Fe1—O8 of 167.93 (14)°. The bond lengths and angles in (I) are similar to those in the related Fe^III complex (Lainé et al.,1995).

In the crystal, the coordinated and crystalline water molecules contribute to the formation of O—H···O hydrogen bonds (Table 1, Fig. 2), which link the molecules into the layers parallel to ab plane.

Related literature top

For related crystal structures, see: Lainé et al. (1995); Wu et al. (2007).

Experimental top

A mixture of Fe₂(SO₄)₃(0.5 mmol), pyco (0.5 mmol), pydc (0.50 mmol), and H₂O (3.00 ml), was placed in a Parr Teflon-lined stainless steel vessel (10 ml), and then the vessel was sealed and heated at 393 K for 3 d. After the mixture was slowly cooled to room temperature, several red crystals of (I) were obtained.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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 (I) showing the atomic numbering and 50% probability displacement ellipsoids.
	Fig. 2. A portion of the crystal packing showing H-bonds as dashed lines.

Aqua(picolinato N-oxide-κ²O¹,O²)(pyridine-2,6- dicarboxylato-κ³O,N,O')iron(III) monohydrate top

Crystal data top

[Fe(C₆H₄NO₃)(C₇H₃NO₄)(H₂O)]·H₂O	Z = 2
M_r = 395.09	F(000) = 402
Triclinic, P1	D_x = 1.791 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.6023 (13) Å	Cell parameters from 544 reflections
b = 7.7256 (16) Å	θ = 2.7–20.0°
c = 15.520 (3) Å	µ = 1.09 mm⁻¹
α = 102.585 (4)°	T = 293 K
β = 95.801 (4)°	Block, red
γ = 105.743 (4)°	0.16 × 0.14 × 0.12 mm
V = 732.7 (3) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	2749 independent reflections
Radiation source: fine-focus sealed tube	1667 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
ϕ and ω scans	θ_max = 25.8°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −8→7
T_min = 0.84, T_max = 0.87	k = −9→9
3915 measured reflections	l = −18→17

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 0.85	w = 1/[σ²(F_o²) + (0.0145P)²] where P = (F_o² + 2F_c²)/3
2749 reflections	(Δ/σ)_max = 0.001
238 parameters	Δρ_max = 0.49 e Å⁻³
4 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

[Fe(C₆H₄NO₃)(C₇H₃NO₄)(H₂O)]·H₂O	γ = 105.743 (4)°
M_r = 395.09	V = 732.7 (3) Å³
Triclinic, P1	Z = 2
a = 6.6023 (13) Å	Mo Kα radiation
b = 7.7256 (16) Å	µ = 1.09 mm⁻¹
c = 15.520 (3) Å	T = 293 K
α = 102.585 (4)°	0.16 × 0.14 × 0.12 mm
β = 95.801 (4)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2749 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	1667 reflections with I > 2σ(I)
T_min = 0.84, T_max = 0.87	R_int = 0.047
3915 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	4 restraints
wR(F²) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 0.85	Δρ_max = 0.49 e Å⁻³
2749 reflections	Δρ_min = −0.36 e Å⁻³
238 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	0.47020 (11)	0.38418 (9)	0.22899 (5)	0.0363 (2)
N1	0.4982 (6)	0.5619 (5)	0.3522 (2)	0.0317 (10)
N2	0.3098 (6)	0.1709 (5)	0.0392 (3)	0.0358 (10)
O1	0.1839 (4)	0.2941 (4)	0.2682 (2)	0.0404 (9)
O4	0.7711 (5)	0.5595 (4)	0.2520 (2)	0.0439 (9)
O5	0.3665 (5)	0.5275 (4)	0.1559 (2)	0.0497 (10)
O8	0.5897 (5)	0.2107 (4)	0.2796 (2)	0.0450 (10)
H8A	0.722 (5)	0.241 (7)	0.300 (3)	0.067*
H8B	0.553 (8)	0.098 (4)	0.276 (4)	0.067*
C1	0.1473 (7)	0.3772 (6)	0.3417 (3)	0.0344 (12)
C2	0.3323 (7)	0.5401 (6)	0.3952 (3)	0.0293 (11)
C3	0.3435 (7)	0.6559 (6)	0.4769 (3)	0.0408 (13)
H3	0.2269	0.6422	0.5066	0.049*
C4	0.5325 (8)	0.7933 (6)	0.5138 (3)	0.0467 (14)
H4	0.5454	0.8734	0.5696	0.056*
C5	0.7012 (7)	0.8134 (6)	0.4693 (3)	0.0448 (14)
H5	0.8294	0.9062	0.4945	0.054*
C6	0.6799 (7)	0.6952 (6)	0.3869 (3)	0.0390 (13)
C7	0.8408 (8)	0.6911 (7)	0.3244 (4)	0.0444 (14)
C8	0.3104 (8)	0.5009 (7)	0.0716 (4)	0.0415 (13)
C9	0.2594 (7)	0.3099 (6)	0.0109 (3)	0.0322 (12)
C10	0.1569 (7)	0.2692 (7)	−0.0765 (3)	0.0444 (14)
H10	0.1215	0.3625	−0.0979	0.053*
C11	0.1064 (8)	0.0935 (7)	−0.1323 (4)	0.0501 (15)
H11	0.0391	0.0679	−0.1913	0.060*
C12	0.1560 (8)	−0.0406 (7)	−0.1002 (4)	0.0462 (14)
H12	0.1214	−0.1602	−0.1373	0.055*
C13	0.2553 (7)	−0.0048 (6)	−0.0149 (3)	0.0377 (13)
H13	0.2863	−0.0996	0.0068	0.045*
O2	−0.0192 (5)	0.3380 (4)	0.3721 (2)	0.0479 (10)
O3	1.0189 (5)	0.8053 (5)	0.3461 (2)	0.0594 (11)
O6	0.2880 (6)	0.6231 (5)	0.0361 (3)	0.0600 (11)
O7	0.4227 (5)	0.1917 (4)	0.1189 (2)	0.0463 (9)
O9	0.3706 (6)	0.8722 (5)	0.2653 (3)	0.0608 (12)
H9A	0.249 (6)	0.839 (7)	0.283 (4)	0.091*
H9B	0.366 (9)	0.771 (5)	0.228 (3)	0.091*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.0375 (4)	0.0354 (4)	0.0324 (4)	0.0069 (3)	0.0085 (3)	0.0053 (3)
N1	0.027 (2)	0.031 (2)	0.036 (3)	0.0067 (18)	0.0058 (19)	0.0084 (19)
N2	0.031 (2)	0.046 (3)	0.028 (3)	0.007 (2)	0.0038 (19)	0.011 (2)
O1	0.0294 (19)	0.040 (2)	0.035 (2)	−0.0034 (15)	0.0042 (16)	−0.0056 (16)
O4	0.033 (2)	0.049 (2)	0.046 (2)	0.0054 (16)	0.0136 (17)	0.0112 (18)
O5	0.069 (3)	0.042 (2)	0.039 (2)	0.0211 (18)	0.004 (2)	0.0075 (18)
O8	0.042 (2)	0.035 (2)	0.051 (3)	0.0033 (19)	−0.0009 (19)	0.0104 (19)
C1	0.029 (3)	0.040 (3)	0.033 (3)	0.009 (2)	−0.001 (2)	0.012 (2)
C2	0.022 (3)	0.032 (3)	0.032 (3)	0.008 (2)	0.000 (2)	0.008 (2)
C3	0.037 (3)	0.047 (3)	0.035 (3)	0.010 (2)	0.009 (2)	0.004 (3)
C4	0.057 (4)	0.041 (3)	0.032 (3)	0.006 (3)	0.003 (3)	0.000 (3)
C5	0.038 (3)	0.037 (3)	0.043 (4)	−0.008 (2)	−0.001 (3)	0.005 (3)
C6	0.036 (3)	0.031 (3)	0.045 (4)	0.002 (2)	0.005 (3)	0.010 (3)
C7	0.040 (3)	0.049 (3)	0.043 (4)	0.007 (3)	0.004 (3)	0.019 (3)
C8	0.033 (3)	0.044 (3)	0.049 (4)	0.010 (3)	0.011 (3)	0.015 (3)
C9	0.031 (3)	0.032 (3)	0.033 (3)	0.005 (2)	0.011 (2)	0.010 (2)
C10	0.035 (3)	0.054 (4)	0.048 (4)	0.011 (3)	0.008 (3)	0.023 (3)
C11	0.050 (4)	0.053 (4)	0.040 (4)	0.010 (3)	0.002 (3)	0.009 (3)
C12	0.036 (3)	0.049 (3)	0.042 (4)	0.007 (3)	0.006 (3)	−0.004 (3)
C13	0.032 (3)	0.033 (3)	0.045 (4)	0.007 (2)	0.013 (3)	0.005 (3)
O2	0.027 (2)	0.061 (2)	0.044 (2)	0.0007 (16)	0.0073 (17)	0.0029 (18)
O3	0.034 (2)	0.063 (2)	0.065 (3)	−0.0095 (18)	0.0098 (19)	0.013 (2)
O6	0.071 (3)	0.051 (2)	0.065 (3)	0.021 (2)	0.007 (2)	0.028 (2)
O7	0.054 (2)	0.055 (2)	0.026 (2)	0.0208 (18)	−0.0004 (18)	0.0015 (17)
O9	0.060 (3)	0.034 (2)	0.079 (3)	0.005 (2)	0.027 (2)	0.000 (2)

Geometric parameters (Å, º) top

Fe1—O7	1.939 (3)	C3—H3	0.9300
Fe1—O5	1.945 (4)	C4—C5	1.360 (6)
Fe1—O8	1.986 (4)	C4—H4	0.9300
Fe1—O4	2.023 (3)	C5—C6	1.369 (6)
Fe1—O1	2.032 (3)	C5—H5	0.9300
Fe1—N1	2.055 (4)	C6—C7	1.511 (6)
N1—C6	1.321 (5)	C7—O3	1.226 (5)
N1—C2	1.331 (5)	C8—O6	1.226 (6)
N2—O7	1.332 (5)	C8—C9	1.496 (6)
N2—C9	1.352 (5)	C9—C10	1.382 (6)
N2—C13	1.362 (5)	C10—C11	1.374 (6)
O1—C1	1.262 (5)	C10—H10	0.9300
O4—C7	1.285 (5)	C11—C12	1.344 (7)
O5—C8	1.279 (6)	C11—H11	0.9300
O8—H8A	0.85 (3)	C12—C13	1.351 (7)
O8—H8B	0.83 (3)	C12—H12	0.9300
C1—O2	1.228 (5)	C13—H13	0.9300
C1—C2	1.507 (6)	O9—H9A	0.87 (3)
C2—C3	1.365 (6)	O9—H9B	0.86 (3)
C3—C4	1.372 (6)

O7—Fe1—O5	86.72 (14)	C2—C3—H3	121.1
O7—Fe1—O8	82.18 (14)	C4—C3—H3	121.1
O5—Fe1—O8	167.93 (15)	C5—C4—C3	120.6 (4)
O7—Fe1—O4	110.22 (14)	C5—C4—H4	119.7
O5—Fe1—O4	91.59 (14)	C3—C4—H4	119.7
O8—Fe1—O4	87.85 (14)	C4—C5—C6	119.1 (4)
O7—Fe1—O1	98.80 (13)	C4—C5—H5	120.4
O5—Fe1—O1	93.23 (14)	C6—C5—H5	120.4
O8—Fe1—O1	93.13 (14)	N1—C6—C5	120.0 (4)
O4—Fe1—O1	150.80 (13)	N1—C6—C7	111.0 (4)
O7—Fe1—N1	172.69 (15)	C5—C6—C7	129.1 (4)
O5—Fe1—N1	97.84 (14)	O3—C7—O4	126.8 (5)
O8—Fe1—N1	93.69 (15)	O3—C7—C6	119.7 (5)
O4—Fe1—N1	75.50 (13)	O4—C7—C6	113.5 (4)
O1—Fe1—N1	75.31 (13)	O6—C8—O5	123.9 (5)
C6—N1—C2	121.5 (4)	O6—C8—C9	116.3 (5)
C6—N1—Fe1	119.4 (3)	O5—C8—C9	119.8 (5)
C2—N1—Fe1	119.1 (3)	N2—C9—C10	117.5 (4)
O7—N2—C9	124.5 (4)	N2—C9—C8	121.7 (5)
O7—N2—C13	113.8 (4)	C10—C9—C8	120.8 (5)
C9—N2—C13	121.6 (4)	C11—C10—C9	121.3 (5)
C1—O1—Fe1	120.7 (3)	C11—C10—H10	119.4
C7—O4—Fe1	120.6 (3)	C9—C10—H10	119.4
C8—O5—Fe1	133.6 (3)	C12—C11—C10	118.8 (5)
Fe1—O8—H8A	121 (3)	C12—C11—H11	120.6
Fe1—O8—H8B	136 (4)	C10—C11—H11	120.6
H8A—O8—H8B	101 (5)	C11—C12—C13	121.2 (5)
O2—C1—O1	126.8 (4)	C11—C12—H12	119.4
O2—C1—C2	118.9 (4)	C13—C12—H12	119.4
O1—C1—C2	114.3 (4)	C12—C13—N2	119.5 (5)
N1—C2—C3	121.0 (4)	C12—C13—H13	120.2
N1—C2—C1	110.7 (4)	N2—C13—H13	120.2
C3—C2—C1	128.3 (4)	N2—O7—Fe1	129.5 (3)
C2—C3—C4	117.8 (4)	H9A—O9—H9B	101 (5)

O7—Fe1—N1—C6	142.0 (11)	C3—C4—C5—C6	0.3 (8)
O5—Fe1—N1—C6	−89.7 (4)	C2—N1—C6—C5	0.7 (8)
O8—Fe1—N1—C6	86.7 (4)	Fe1—N1—C6—C5	−179.4 (4)
O4—Fe1—N1—C6	−0.1 (4)	C2—N1—C6—C7	−179.3 (4)
O1—Fe1—N1—C6	179.0 (4)	Fe1—N1—C6—C7	0.6 (5)
O7—Fe1—N1—C2	−38.1 (14)	C4—C5—C6—N1	−1.0 (8)
O5—Fe1—N1—C2	90.2 (4)	C4—C5—C6—C7	179.0 (5)
O8—Fe1—N1—C2	−93.4 (4)	Fe1—O4—C7—O3	179.8 (4)
O4—Fe1—N1—C2	179.8 (4)	Fe1—O4—C7—C6	1.0 (6)
O1—Fe1—N1—C2	−1.1 (3)	N1—C6—C7—O3	−179.9 (5)
O7—Fe1—O1—C1	176.8 (4)	C5—C6—C7—O3	0.1 (9)
O5—Fe1—O1—C1	−96.0 (4)	N1—C6—C7—O4	−1.0 (6)
O8—Fe1—O1—C1	94.3 (4)	C5—C6—C7—O4	179.0 (5)
O4—Fe1—O1—C1	3.1 (5)	Fe1—O5—C8—O6	−165.3 (3)
N1—Fe1—O1—C1	1.3 (4)	Fe1—O5—C8—C9	17.2 (7)
O7—Fe1—O4—C7	−175.7 (4)	O7—N2—C9—C10	174.6 (4)
O5—Fe1—O4—C7	97.2 (4)	C13—N2—C9—C10	−2.3 (6)
O8—Fe1—O4—C7	−94.9 (4)	O7—N2—C9—C8	−5.9 (7)
O1—Fe1—O4—C7	−2.3 (5)	C13—N2—C9—C8	177.2 (4)
N1—Fe1—O4—C7	−0.5 (4)	O6—C8—C9—N2	169.3 (4)
O7—Fe1—O5—C8	−4.4 (5)	O5—C8—C9—N2	−13.0 (7)
O8—Fe1—O5—C8	18.6 (10)	O6—C8—C9—C10	−11.3 (7)
O4—Fe1—O5—C8	105.7 (5)	O5—C8—C9—C10	166.5 (5)
O1—Fe1—O5—C8	−103.1 (5)	N2—C9—C10—C11	0.6 (7)
N1—Fe1—O5—C8	−178.7 (5)	C8—C9—C10—C11	−178.9 (4)
Fe1—O1—C1—O2	179.0 (4)	C9—C10—C11—C12	0.8 (8)
Fe1—O1—C1—C2	−1.2 (5)	C10—C11—C12—C13	−0.5 (8)
C6—N1—C2—C3	0.4 (7)	C11—C12—C13—N2	−1.2 (8)
Fe1—N1—C2—C3	−179.5 (3)	O7—N2—C13—C12	−174.5 (4)
C6—N1—C2—C1	−179.2 (4)	C9—N2—C13—C12	2.7 (7)
Fe1—N1—C2—C1	0.8 (5)	C9—N2—O7—Fe1	22.0 (6)
O2—C1—C2—N1	−180.0 (4)	C13—N2—O7—Fe1	−160.9 (3)
O1—C1—C2—N1	0.2 (6)	O5—Fe1—O7—N2	−15.4 (4)
O2—C1—C2—C3	0.4 (8)	O8—Fe1—O7—N2	169.3 (4)
O1—C1—C2—C3	−179.4 (5)	O4—Fe1—O7—N2	−105.9 (4)
N1—C2—C3—C4	−1.1 (7)	O1—Fe1—O7—N2	77.3 (4)
C1—C2—C3—C4	178.5 (5)	N1—Fe1—O7—N2	113.4 (12)
C2—C3—C4—C5	0.7 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O8—H8A···O2ⁱ	0.85 (4)	1.81 (4)	2.637 (5)	164 (4)
O8—H8B···O9ⁱⁱ	0.83 (3)	1.79 (4)	2.571 (5)	157 (5)
O9—H9A···O3ⁱⁱⁱ	0.87 (5)	1.88 (5)	2.730 (5)	167 (5)
O9—H9B···O5	0.86 (5)	1.97 (6)	2.821 (5)	173 (4)

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

Experimental details

Crystal data
Chemical formula	[Fe(C₆H₄NO₃)(C₇H₃NO₄)(H₂O)]·H₂O
M_r	395.09
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	6.6023 (13), 7.7256 (16), 15.520 (3)
α, β, γ (°)	102.585 (4), 95.801 (4), 105.743 (4)
V (Å³)	732.7 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.09
Crystal size (mm)	0.16 × 0.14 × 0.12

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2000)
T_min, T_max	0.84, 0.87
No. of measured, independent and observed [I > 2σ(I)] reflections	3915, 2749, 1667
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.611

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.096, 0.85
No. of reflections	2749
No. of parameters	238
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.36

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), 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
O8—H8A···O2ⁱ	0.85 (4)	1.81 (4)	2.637 (5)	164 (4)
O8—H8B···O9ⁱⁱ	0.83 (3)	1.79 (4)	2.571 (5)	157 (5)
O9—H9A···O3ⁱⁱⁱ	0.87 (5)	1.88 (5)	2.730 (5)	167 (5)
O9—H9B···O5	0.86 (5)	1.97 (6)	2.821 (5)	173 (4)

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

References

Bruker (2001). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Lainé, P., Gourdon, A. & Launay, J. P. (1995). Inorg. Chem. 34, 5129–5137. 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
Wu, W. P., Wang, Y. Y., Wu, Y. P., Liu, J. Q., Zeng, X. R., Shi, Q. Z. & Peng, S. M. (2007). CrystEngComm, 9, 753–757. Web of Science CSD CrossRef CAS Google Scholar

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Volume 64| Part 10| October 2008| Page m1343

doi:10.1107/S1600536808030663

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