catena-Poly[[aqua­(dipyrido[3,2-a:2′,3′-c]phenazine-κ2N4,N5)iron(II)]-μ-pyrazine-2,3-dicarboxyl­ato-κ3N1,O2:O3]

Xu, Z.-L.; Li, X.-Y.; Che, G.-B.; Lu, L.; Xu, C.-H.

doi:10.1107/S1600536808027153

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Pages m1243-m1244

doi:10.1107/S1600536808027153

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catena-Poly[[aqua(dipyrido[3,2-a:2′,3′-c]phenazine-κ²N⁴,N⁵)iron(II)]-μ-pyrazine-2,3-dicarboxylato-κ³N¹,O²:O³]

Zhan-Lin Xu,^a Xiu-Ying Li,^a Guang-Bo Che,^a ^* Lu Lu ^a and Chun-Hui Xu ^a

^aDepartment of Chemistry, Jilin Normal University, Siping 136000, People's Republic of China
^*Correspondence e-mail: guangbochejl@yahoo.com

(Received 31 July 2008; accepted 23 August 2008; online 6 September 2008)

In the title compound, [Fe(C₆H₂N₂O₄)(C₁₈H₁₀N₄)(H₂O)]_n, the Fe^II ion adopts a slightly distorted octahedral mer-FeN₃O₃ geometry, arising from one N,N′-bidentate dipyrido[3,2-a:2′,3′-c]phenazine ligand, one N,O-chelating pyrazine-2,3-dicarboxylate dianion and one water molecule. An O-bonded symmetry-related dianion completes the coordination of the metal. The bridging dianion results in a one-dimensional polymeric chain. Aromatic π–π stacking interactions between ligands [centroid–centroid separations = 3.528 (2) and 3.741 (2) Å] and O—H⋯O and O—H⋯N hydrogen bonds link the chains together, leading to a three-dimensional supramolecular network.

Related literature

For related literature, see: Che et al. (2006 ); Stephenson & Hardie (2006 ); Wang et al. (2008 ); Xu et al. (2008 ).

Experimental

Crystal data

[Fe(C₆H₂N₂O₄)(C₁₈H₁₀N₄)(H₂O)]
M_r = 522.26
Triclinic, $[P \overline 1]$
a = 6.7868 (14) Å
b = 7.4586 (15) Å
c = 20.548 (4) Å
α = 90.75 (3)°
β = 95.89 (3)°
γ = 98.54 (3)°
V = 1022.8 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.79 mm⁻¹
T = 292 (2) K
0.35 × 0.30 × 0.25 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.756, T_max = 0.821
10101 measured reflections
4633 independent reflections
2914 reflections with I > 2σ(I)
R_int = 0.056

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.129
S = 1.04
4633 reflections
333 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.45 e Å⁻³

Table 1
Selected bond lengths (Å)

Fe—N5	2.160 (3)
Fe—N2	2.172 (3)
Fe—N1	2.193 (3)
Fe—O3ⁱ	2.042 (3)
Fe—O1	2.113 (3)
Fe—O1W	2.148 (3)
Symmetry code: (i) x, y+1, z.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—HW1B⋯O4ⁱⁱ	0.89 (7)	1.79 (7)	2.649 (4)	161 (5)
O1W—HW1A⋯N6ⁱⁱⁱ	0.81 (5)	2.05 (5)	2.861 (4)	176 (5)
Symmetry codes: (ii) x+1, y+1, z; (iii) -x, -y, -z.

Data collection: PROCESS-AUTO (Rigaku, 1998 ); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808027153/hb2771sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808027153/hb2771Isup2.hkl

checkCIF report

Comment top

Dipyrido[3,2-a:2',3'-c]phenazine (DPPZ) is an important derivative of 1,10-phenanthroline (phen), having often been used to build novel supramolecular architectures due to its excellent coordinating ability to metals and its rigid planar aromatic ring system (Stephenson & Hardie, 2006). A few complexes containing DPPZ in combination with doubly-deprotonated pyrazine-2,3-dicarboxylic acid (H₂PZDC) have been reported (Xu et al., 2008; Wang et al., 2008). As a continuation of this work, we selected H₂PZDC as a linker ligand and DPPZ as a secondary chelating ligand, generating a new coordination polymer, [Fe(DPPZ)(PZDC)(H₂O)]_n, (I), which is reported here.

The Fe(II) atom is bonded to three nitrogen atoms (N1, N2, N5) from one DPPZ ligand and one PZDC ligand, and three oxygen atoms (O1, O3ⁱ, O1W) from two PZDC ligands and one water molecule in a slightly distorted octahedral coordination geometry (Table 1). The mean bond distances are Fe—N = 2.175 (3) Å and Fe—O = 2.101 (3) Å. The N1, N2, N5, O1W atoms comprise the basal plane, while the O1 and O3 atoms occupy the axial position (Fig. 1). The PZDC^2- dianion adopts chelating and bridging coordination modes, linking the adjacent Fe atoms into a distinctive one-dimensional chain propagating along the b axis, and the DPPZ ligands are attached to one side of the chain. The neighboring one-dimensional chains interact by π-π stacking between the dppz ligands [centroid separation = 3.741 (2) Å], at the same time, the π-π type interactions between two PZDC^2- ligands occur [centroid separation = 3.528 (2) Å]. In this way, these neighboring one-dimensional chains are linked into an intriguing three-dimensional supramolecular motif (Fig. 2). Furthermore, O—H···O and O—H···N hydrogen bonds between the O1W atom and the O4, N6 atoms of the PZDC^2- dianion further consolidate the three-dimensional architecture (Table 2).

Related literature top

For related literature, see: Che et al. (2006); Stephenson & Hardie (2006); Wang et al. (2008); Xu et al. (2008).

Experimental top

The DPPZ ligand was synthesized according to the literature method (Che, Li et al., 2006). A mixture of DPPZ, H₂PZDC, FeSO₄ and water in a molar ratio of 1:1:1:5000 was sealed in a Teflon-lined autoclave and heated to 433 K for 3 d. Upon cooling and opening the bomb, brown blocks of (I) were obtained (75% yield based on Fe).

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: PROCESS-AUTO (Rigaku, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of (I), expanded to show the metal coordination sphere. Displacement ellipsoids are drawn at the 20% probability level (arbitrary spheres for the H atoms). [Symmetry code: (i) x, y + 1, z.]
	Fig. 2. Packing diagram of the three-dimensional supramolecular structure of (I) formed via π-π interactions. H atoms have been omitted.

catena-Poly[[aqua(dipyrido[3,2-a:2',3'-c]phenazine-κ²N⁴,N⁵)iron(II)]-µ- pyrazine-2,3-dicarboxylato-κ³N¹,O²:O³] top

Crystal data top

[Fe(C₆H₂N₂O₄)(C₁₈H₁₀N₄)(H₂O)]	Z = 2
M_r = 522.26	F(000) = 532
Triclinic, P1	D_x = 1.696 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.7868 (14) Å	Cell parameters from 2687 reflections
b = 7.4586 (15) Å	θ = 3.0–27.5°
c = 20.548 (4) Å	µ = 0.79 mm⁻¹
α = 90.75 (3)°	T = 292 K
β = 95.89 (3)°	Block, brown
γ = 98.54 (3)°	0.35 × 0.30 × 0.25 mm
V = 1022.8 (4) Å³

Data collection top

Rigaku R-AXIS RAPID diffractometer	4633 independent reflections
Radiation source: fine-focus sealed tube	2914 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.056
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.5°, θ_min = 3.0°
ω scans	h = −8→8
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −9→8
T_min = 0.756, T_max = 0.821	l = −25→26
10101 measured reflections

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)] = 0.056	Hydrogen site location: difmap and geom
wR(F²) = 0.129	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0428P)² + 1.0171P] where P = (F_o² + 2F_c²)/3
4633 reflections	(Δ/σ)_max = 0.004
333 parameters	Δρ_max = 0.47 e Å⁻³
0 restraints	Δρ_min = −0.45 e Å⁻³

Crystal data top

[Fe(C₆H₂N₂O₄)(C₁₈H₁₀N₄)(H₂O)]	γ = 98.54 (3)°
M_r = 522.26	V = 1022.8 (4) Å³
Triclinic, P1	Z = 2
a = 6.7868 (14) Å	Mo Kα radiation
b = 7.4586 (15) Å	µ = 0.79 mm⁻¹
c = 20.548 (4) Å	T = 292 K
α = 90.75 (3)°	0.35 × 0.30 × 0.25 mm
β = 95.89 (3)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	4633 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	2914 reflections with I > 2σ(I)
T_min = 0.756, T_max = 0.821	R_int = 0.056
10101 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.129	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.47 e Å⁻³
4633 reflections	Δρ_min = −0.45 e Å⁻³
333 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
C1	−0.3579 (6)	0.3353 (5)	0.21577 (19)	0.0391 (10)
H1	−0.4134	0.2742	0.1769	0.047*
C2	−0.4714 (6)	0.3250 (5)	0.26882 (19)	0.0399 (10)
H2	−0.5990	0.2575	0.2657	0.048*
C3	−0.3893 (6)	0.4177 (5)	0.32583 (19)	0.0391 (9)
H3	−0.4625	0.4147	0.3618	0.047*
C4	−0.1974 (5)	0.5158 (5)	0.32993 (17)	0.0309 (8)
C5	−0.1015 (6)	0.6154 (5)	0.38923 (17)	0.0324 (8)
C6	−0.1076 (7)	0.7026 (5)	0.49600 (18)	0.0410 (10)
C7	−0.2116 (8)	0.7065 (6)	0.5526 (2)	0.0536 (12)
H7	−0.3433	0.6493	0.5517	0.064*
C8	−0.1156 (8)	0.7952 (6)	0.6082 (2)	0.0563 (13)
H8	−0.1829	0.7977	0.6454	0.068*
C9	0.0830 (8)	0.8825 (6)	0.6102 (2)	0.0545 (13)
H9	0.1454	0.9415	0.6487	0.065*
C10	0.1856 (7)	0.8821 (6)	0.55679 (19)	0.0478 (11)
H10	0.3172	0.9404	0.5588	0.057*
C11	0.0912 (7)	0.7924 (5)	0.49774 (18)	0.0391 (10)
C12	0.0969 (6)	0.7099 (5)	0.39062 (18)	0.0350 (9)
C13	0.2008 (6)	0.7143 (5)	0.33132 (17)	0.0324 (8)
C14	0.3877 (6)	0.8170 (5)	0.3279 (2)	0.0431 (10)
H14	0.4520	0.8862	0.3640	0.052*
C15	0.4771 (6)	0.8157 (5)	0.2708 (2)	0.0422 (10)
H15	0.5998	0.8873	0.2673	0.051*
C16	0.3807 (6)	0.7056 (5)	0.21845 (19)	0.0370 (9)
H16	0.4438	0.7016	0.1805	0.044*
C17	0.1100 (6)	0.6141 (5)	0.27547 (17)	0.0305 (8)
C18	−0.0933 (5)	0.5160 (5)	0.27466 (17)	0.0293 (8)
C19	−0.2089 (6)	0.2259 (5)	0.01794 (18)	0.0336 (9)
H19	−0.2207	0.3400	0.0016	0.040*
C20	−0.2698 (6)	0.0736 (5)	−0.02246 (18)	0.0365 (9)
H20	−0.3164	0.0881	−0.0660	0.044*
C21	−0.1979 (5)	−0.1099 (5)	0.06260 (18)	0.0303 (8)
C22	−0.1288 (5)	0.0440 (5)	0.10284 (17)	0.0285 (8)
C23	−0.0384 (6)	0.0397 (5)	0.17379 (18)	0.0346 (9)
C24	−0.2043 (5)	−0.2964 (5)	0.08552 (16)	0.0297 (8)
N1	−0.1746 (5)	0.4280 (4)	0.21800 (14)	0.0331 (7)
N2	0.2019 (5)	0.6055 (4)	0.22036 (14)	0.0314 (7)
N3	−0.2043 (5)	0.6123 (4)	0.44118 (15)	0.0411 (8)
N4	0.1938 (5)	0.7950 (4)	0.44469 (15)	0.0392 (8)
N5	−0.1343 (5)	0.2118 (4)	0.07921 (14)	0.0305 (7)
N6	−0.2634 (5)	−0.0942 (4)	−0.00061 (15)	0.0352 (8)
O1	0.0834 (4)	0.1821 (3)	0.19258 (13)	0.0424 (7)
O2	−0.0907 (5)	−0.0942 (4)	0.20571 (14)	0.0510 (8)
O1W	0.2777 (5)	0.4031 (4)	0.08593 (15)	0.0452 (8)
O3	−0.0399 (4)	−0.3617 (3)	0.09209 (12)	0.0375 (6)
O4	−0.3708 (5)	−0.3852 (4)	0.09181 (15)	0.0550 (9)
Fe	0.03575 (9)	0.42245 (7)	0.14403 (3)	0.03090 (17)
HW1B	0.402 (10)	0.456 (8)	0.081 (3)	0.10 (2)*
HW1A	0.279 (7)	0.315 (7)	0.063 (2)	0.056 (15)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.039 (2)	0.038 (2)	0.036 (2)	−0.0039 (18)	−0.0006 (17)	−0.0008 (18)
C2	0.030 (2)	0.041 (2)	0.044 (2)	−0.0067 (18)	0.0026 (17)	0.0041 (19)
C3	0.041 (2)	0.044 (2)	0.033 (2)	0.0053 (19)	0.0061 (17)	0.0035 (18)
C4	0.029 (2)	0.0298 (19)	0.0337 (19)	0.0028 (16)	0.0041 (16)	0.0019 (16)
C5	0.040 (2)	0.0282 (19)	0.0289 (18)	0.0044 (16)	0.0051 (16)	0.0016 (16)
C6	0.056 (3)	0.037 (2)	0.031 (2)	0.011 (2)	0.0028 (18)	0.0013 (17)
C7	0.070 (3)	0.051 (3)	0.041 (2)	0.007 (2)	0.015 (2)	0.000 (2)
C8	0.090 (4)	0.051 (3)	0.032 (2)	0.021 (3)	0.015 (2)	−0.005 (2)
C9	0.085 (4)	0.045 (3)	0.033 (2)	0.015 (3)	−0.002 (2)	−0.006 (2)
C10	0.059 (3)	0.046 (3)	0.036 (2)	0.010 (2)	−0.005 (2)	−0.008 (2)
C11	0.053 (3)	0.033 (2)	0.031 (2)	0.0098 (19)	0.0004 (18)	−0.0010 (17)
C12	0.041 (2)	0.0308 (19)	0.0328 (19)	0.0059 (17)	0.0011 (17)	0.0008 (16)
C13	0.035 (2)	0.0278 (18)	0.0330 (19)	−0.0015 (16)	0.0030 (16)	−0.0010 (16)
C14	0.043 (3)	0.040 (2)	0.042 (2)	−0.0042 (19)	0.0025 (19)	−0.0093 (19)
C15	0.038 (2)	0.036 (2)	0.049 (2)	−0.0087 (18)	0.0076 (19)	−0.0047 (19)
C16	0.035 (2)	0.034 (2)	0.042 (2)	−0.0001 (17)	0.0087 (17)	0.0003 (18)
C17	0.030 (2)	0.0255 (18)	0.0344 (19)	−0.0007 (15)	0.0022 (15)	0.0026 (15)
C18	0.029 (2)	0.0276 (18)	0.0294 (18)	0.0002 (15)	0.0014 (15)	0.0032 (15)
C19	0.034 (2)	0.0312 (19)	0.036 (2)	0.0045 (16)	0.0067 (17)	0.0019 (16)
C20	0.036 (2)	0.042 (2)	0.0302 (19)	0.0026 (18)	0.0027 (16)	−0.0011 (17)
C21	0.0236 (19)	0.0274 (18)	0.040 (2)	0.0028 (15)	0.0058 (16)	−0.0001 (16)
C22	0.028 (2)	0.0237 (17)	0.0336 (19)	0.0007 (15)	0.0061 (15)	−0.0034 (15)
C23	0.039 (2)	0.030 (2)	0.0343 (19)	0.0043 (17)	0.0038 (17)	0.0022 (17)
C24	0.025 (2)	0.038 (2)	0.0240 (17)	−0.0043 (16)	0.0053 (15)	−0.0002 (15)
N1	0.0338 (18)	0.0331 (16)	0.0300 (15)	−0.0017 (14)	0.0028 (13)	−0.0009 (14)
N2	0.0305 (18)	0.0305 (16)	0.0324 (16)	0.0011 (13)	0.0048 (13)	0.0000 (13)
N3	0.050 (2)	0.0378 (19)	0.0347 (17)	0.0026 (16)	0.0059 (16)	0.0009 (15)
N4	0.046 (2)	0.0376 (18)	0.0330 (17)	0.0071 (16)	0.0007 (15)	−0.0060 (15)
N5	0.0311 (18)	0.0252 (15)	0.0344 (16)	0.0002 (13)	0.0062 (13)	−0.0005 (13)
N6	0.0367 (19)	0.0315 (17)	0.0354 (17)	−0.0023 (14)	0.0055 (14)	−0.0050 (14)
O1	0.0450 (17)	0.0328 (15)	0.0445 (16)	0.0000 (13)	−0.0099 (13)	0.0003 (13)
O2	0.068 (2)	0.0383 (16)	0.0451 (16)	0.0004 (15)	0.0098 (15)	0.0096 (14)
O1W	0.0364 (18)	0.0424 (17)	0.0549 (18)	−0.0070 (14)	0.0172 (14)	−0.0195 (15)
O3	0.0453 (18)	0.0302 (14)	0.0388 (14)	0.0069 (12)	0.0114 (13)	0.0064 (12)
O4	0.047 (2)	0.0442 (17)	0.068 (2)	−0.0158 (15)	0.0120 (16)	0.0024 (15)
Fe	0.0342 (3)	0.0253 (3)	0.0314 (3)	−0.0014 (2)	0.0042 (2)	−0.0020 (2)

Geometric parameters (Å, º) top

C1—N1	1.326 (5)	C15—H15	0.9300
C1—C2	1.395 (5)	C16—N2	1.331 (5)
C1—H1	0.9300	C16—H16	0.9300
C2—C3	1.375 (5)	C17—N2	1.353 (4)
C2—H2	0.9300	C17—C18	1.461 (5)
C3—C4	1.390 (5)	C18—N1	1.353 (4)
C3—H3	0.9300	C19—N5	1.319 (5)
C4—C18	1.398 (5)	C19—C20	1.384 (5)
C4—C5	1.460 (5)	C19—H19	0.9300
C5—N3	1.332 (5)	C20—N6	1.340 (5)
C5—C12	1.421 (5)	C20—H20	0.9300
C6—N3	1.360 (5)	C21—N6	1.341 (5)
C6—C11	1.412 (6)	C21—C22	1.399 (5)
C6—C7	1.423 (6)	C21—C24	1.471 (5)
C7—C8	1.368 (6)	C22—N5	1.353 (4)
C7—H7	0.9300	C22—C23	1.525 (5)
C8—C9	1.403 (7)	C23—O2	1.230 (4)
C8—H8	0.9300	C23—O1	1.274 (4)
C9—C10	1.360 (6)	C24—O4	1.242 (4)
C9—H9	0.9300	C24—O3	1.278 (5)
C10—C11	1.422 (5)	Fe—N5	2.160 (3)
C10—H10	0.9300	Fe—N2	2.172 (3)
C11—N4	1.351 (5)	Fe—N1	2.193 (3)
C12—N4	1.333 (5)	Fe—O3ⁱ	2.042 (3)
C12—C13	1.468 (5)	Fe—O1	2.113 (3)
C13—C14	1.390 (5)	Fe—O1W	2.148 (3)
C13—C17	1.397 (5)	O1W—HW1B	0.89 (7)
C14—C15	1.375 (6)	O1W—HW1A	0.81 (5)
C14—H14	0.9300	O3—Feⁱⁱ	2.042 (3)
C15—C16	1.391 (5)

N1—C1—C2	123.2 (3)	N1—C18—C17	116.7 (3)
N1—C1—H1	118.4	C4—C18—C17	121.0 (3)
C2—C1—H1	118.4	N5—C19—C20	121.1 (4)
C3—C2—C1	118.0 (4)	N5—C19—H19	119.5
C3—C2—H2	121.0	C20—C19—H19	119.5
C1—C2—H2	121.0	N6—C20—C19	121.8 (4)
C2—C3—C4	120.2 (4)	N6—C20—H20	119.1
C2—C3—H3	119.9	C19—C20—H20	119.1
C4—C3—H3	119.9	N6—C21—C22	120.8 (3)
C3—C4—C18	117.8 (3)	N6—C21—C24	115.7 (3)
C3—C4—C5	122.8 (3)	C22—C21—C24	123.5 (3)
C18—C4—C5	119.4 (3)	N5—C22—C21	120.4 (3)
N3—C5—C12	122.0 (3)	N5—C22—C23	115.0 (3)
N3—C5—C4	118.1 (3)	C21—C22—C23	124.6 (3)
C12—C5—C4	120.0 (3)	O2—C23—O1	128.1 (4)
N3—C6—C11	121.7 (4)	O2—C23—C22	118.3 (3)
N3—C6—C7	118.6 (4)	O1—C23—C22	113.5 (3)
C11—C6—C7	119.7 (4)	O4—C24—O3	124.1 (4)
C8—C7—C6	119.2 (5)	O4—C24—C21	117.9 (4)
C8—C7—H7	120.4	O3—C24—C21	117.6 (3)
C6—C7—H7	120.4	C1—N1—C18	118.4 (3)
C7—C8—C9	121.0 (4)	C1—N1—Fe	126.7 (2)
C7—C8—H8	119.5	C18—N1—Fe	114.2 (2)
C9—C8—H8	119.5	C16—N2—C17	118.2 (3)
C10—C9—C8	121.0 (4)	C16—N2—Fe	127.2 (2)
C10—C9—H9	119.5	C17—N2—Fe	114.6 (2)
C8—C9—H9	119.5	C5—N3—C6	116.2 (4)
C9—C10—C11	119.8 (4)	C12—N4—C11	116.6 (4)
C9—C10—H10	120.1	C19—N5—C22	118.3 (3)
C11—C10—H10	120.1	C19—N5—Fe	128.0 (3)
N4—C11—C6	121.6 (3)	C22—N5—Fe	112.6 (2)
N4—C11—C10	119.3 (4)	C20—N6—C21	117.4 (3)
C6—C11—C10	119.1 (4)	C23—O1—Fe	116.1 (2)
N4—C12—C5	121.9 (3)	Fe—O1W—HW1B	141 (4)
N4—C12—C13	118.3 (3)	Fe—O1W—HW1A	122 (3)
C5—C12—C13	119.8 (3)	HW1B—O1W—HW1A	97 (5)
C14—C13—C17	117.8 (3)	C24—O3—Feⁱⁱ	130.2 (2)
C14—C13—C12	122.5 (3)	O3ⁱ—Fe—O1	173.46 (11)
C17—C13—C12	119.7 (3)	O3ⁱ—Fe—O1W	90.86 (12)
C15—C14—C13	119.7 (4)	O1—Fe—O1W	91.40 (13)
C15—C14—H14	120.1	O3ⁱ—Fe—N5	97.15 (12)
C13—C14—H14	120.1	O1—Fe—N5	76.90 (11)
C14—C15—C16	118.8 (4)	O1W—Fe—N5	85.84 (12)
C14—C15—H15	120.6	O3ⁱ—Fe—N2	90.36 (11)
C16—C15—H15	120.6	O1—Fe—N2	95.42 (11)
N2—C16—C15	122.8 (4)	O1W—Fe—N2	97.75 (12)
N2—C16—H16	118.6	N5—Fe—N2	171.65 (12)
C15—C16—H16	118.6	O3ⁱ—Fe—N1	97.51 (12)
N2—C17—C13	122.5 (3)	O1—Fe—N1	80.95 (12)
N2—C17—C18	117.4 (3)	O1W—Fe—N1	169.62 (13)
C13—C17—C18	120.0 (3)	N5—Fe—N1	99.12 (11)
N1—C18—C4	122.3 (3)	N2—Fe—N1	76.17 (11)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—HW1B···O4ⁱⁱⁱ	0.89 (7)	1.79 (7)	2.649 (4)	161 (5)
O1W—HW1A···N6^iv	0.81 (5)	2.05 (5)	2.861 (4)	176 (5)

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

Experimental details

Crystal data
Chemical formula	[Fe(C₆H₂N₂O₄)(C₁₈H₁₀N₄)(H₂O)]
M_r	522.26
Crystal system, space group	Triclinic, P1
Temperature (K)	292
a, b, c (Å)	6.7868 (14), 7.4586 (15), 20.548 (4)
α, β, γ (°)	90.75 (3), 95.89 (3), 98.54 (3)
V (Å³)	1022.8 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.79
Crystal size (mm)	0.35 × 0.30 × 0.25

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.756, 0.821
No. of measured, independent and observed [I > 2σ(I)] reflections	10101, 4633, 2914
R_int	0.056
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.129, 1.04
No. of reflections	4633
No. of parameters	333
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.45

Computer programs: PROCESS-AUTO (Rigaku, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL-Plus (Sheldrick, 2008).

Selected bond lengths (Å) top

Fe—N5	2.160 (3)	Fe—O3ⁱ	2.042 (3)
Fe—N2	2.172 (3)	Fe—O1	2.113 (3)
Fe—N1	2.193 (3)	Fe—O1W	2.148 (3)

Symmetry code: (i) x, y+1, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—HW1B···O4ⁱⁱ	0.89 (7)	1.79 (7)	2.649 (4)	161 (5)
O1W—HW1A···N6ⁱⁱⁱ	0.81 (5)	2.05 (5)	2.861 (4)	176 (5)

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

Acknowledgements

The authors thank the Doctoral Foundation of Jilin Normal University (No. 2006006 and No. 2007009) and the Subject and Base Construction Foundation of Jilin Normal University (No. 2006041).

References

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