2,9-Dimethyl-1,10-phenanthrolinium bis­(pyridine-2,6-dicarboxyl­ato-κ3O,N,O′)ferrate(III) dihydrate

Aghabozorg, H.; Sadrkhanlou, E.; Soleimannejad, J.; Adams, H.

doi:10.1107/S1600536807025081

2,9-Dimethyl-1,10-phenanthrolinium bis(pyridine-2,6-dicarboxylato-κ³O,N,O′)ferrate(III) dihydrate

H. Aghabozorg, E. Sadrkhanlou, J. Soleimannejad and H. Adams

The title compound, (C₁₄H₁₃N₂)[Fe(C₇H₃NO₄)₂]·2H₂O or (dmpH)[Fe(pydc)₂]·2H₂O (dmp is 2,9-dimethyl-1,10-phenanthroline and pydcH₂ is pyridine-2,6-dicarboxylic acid), is a six-coordinate Fe^III complex obtained by reacting neocuproine (dmp), dipicolinic acid (pydcH₂) and iron(II) chloride. The anionic six-coordinate complex has a distorted octahedral geometry and is connected to its counter-cation by a number of intermolecular interactions, forming infinite one-dimensional chains in the [010] direction. Ion pairing, metal–ligand coordination and van der Waals forces, as well as intermolecular X—H

O hydrogen bonds (X = O, N and C) and π–π stacking interactions [with centroid-to-centroid separations of 3.531 and 3.457 Å, shortest interplanar distances of 3.355 and 3.449 Å, and interplanar angles of 1.89 and 5.45°], result in a three-dimensional framework.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807025081/bh2100sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807025081/bh2100Isup2.hkl Contains datablock I

CCDC reference: 635308

checkCIF report

Key indicators

Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.006 Å
R factor = 0.058
wR factor = 0.165
Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT417_ALERT_2_B Short Inter D-H..H-D       H9B    ..  H10B    ..       1.38 Ang.

Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.127
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.13
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         46 Perc.
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT432_ALERT_2_C Short Inter X...Y Contact  C5     ..  C5      ..       3.15 Ang.

Alert level G
PLAT794_ALERT_5_G Check Predicted Bond Valency for Fe1         (3)       3.07

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

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

Comment top

Continuing our research on proton-transfer compounds, we reached a system which is highly soluble in polar solvents. This compound has not been crystallized until now, but its metal-organic derivatives can be obtained as suitable crystals. In this report, the crystal structure of the iron(III) derivative is described.

The Fe^III ion is located at the centre of a distorted octahedral arrangement (Fig. 1). The O1—Fe1—O5—C8 [92.4 (3)°], O1—Fe1—O8—C14 [-91.4 (3)°], O8—Fe1—O1—C1 [-96.6 (3)°] and O8—Fe1—O4—C7 [98.1 (3)°] torsion angles, and O1—Fe1—O8 [95.78 (12)°] and O4—Fe1—O5 [94.88 (11)°] bond angles indicate that the dianionic pydc^2- units are almost perpendicular to each other. The important characteristic of the crystal structure is the infinite one dimensional chains based on [010] vector. Figure 2 shows the wavy chains of [Fe(pydc)₂]^- complex anions formed through the C—H···O interactions, in which the R₂²(10) and C₂²(16) graph set can be observed. The space between two chains is filled with dmpH⁺ cations and lattice water molecules. Hydrogen bonds play an important role in stabilizing the crystal structure.

Other intermolecular interactions exist between aromatic cations and the ligands bonded to the metal center. The centroid to centroid separation between the π–systems of the cation, labeled as B, and the anion, A1 and A2, are 3.531 and 3.457 Å, respectively (Fig. 3). The shortest interplanar distances for A1/B (3.355 Å) and A2/B (3.449 Å) and their related interplanar angles, 1.89 and 5.45°, respectively, confirm the effective π–π stacking interactions. Therefore, in the formation of this Fe^III complex, ion pairing, metal–ligand coordinations, hydrogen–bonding and π–π stacking as well as van der Waals forces, play important roles in the construction of the observed three–dimensional network.

Related literature top

There are several reports on proton transfer between a carboxylic acid and a heterocyclic amine, and on the ability of the resulting self-associated proton-transfer systems to react with metal ions, affording transition metal complexes (Aghabozorg et al., 2006; Zhao et al., 2005).

Experimental top

A solution of FeCl₂ (50 mg, 0.25 mmol) in water (10 ml) was added to 10 ml of an aqueous solution of dmp (105 mg, 0.5 mmol) and pydcH₂ (69 mg, 0.5 mmol). Pale yellow crystals of the title compound were obtained after allowing the mixture to stand for a week at room temperature.

Structure description top

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. The asymmetric unit of the title compound, with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. A view of the chains formed by C—H···O interactions; water molecules (yellow and purple) are located in the space between chains and connected via O—H···O hydrogen bonds; dmpH⁺ cations are omitted for clarity.
	Fig. 3. Representation of separations between cation and anions.

2,9-Dimethyl-1,10-phenanthrolinium bis(pyridine-2,6-dicarboxylato-κ³O,N,O')ferrate(III) dihydrate top

Crystal data top

(C₁₄H₁₃N₂)[Fe(C₇H₃NO₄)₂]·2H₂O	F(000) = 1300
M_r = 631.35	D_x = 1.612 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3591 reflections
a = 8.9535 (14) Å	θ = 2.5–25.3°
b = 18.607 (3) Å	µ = 0.65 mm⁻¹
c = 15.674 (2) Å	T = 150 K
β = 94.826 (3)°	Plate, pale yellow
V = 2602.1 (7) Å³	0.50 × 0.40 × 0.08 mm
Z = 4

Data collection top

Bruker SMART diffractometer	5986 independent reflections
Radiation source: fine-focus sealed tube	2776 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.127
Detector resolution: 100 pixels mm^-1	θ_max = 27.7°, θ_min = 1.7°
ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	k = −24→23
T_min = 0.737, T_max = 0.950	l = −20→20
29654 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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.165	H-atom parameters constrained
S = 0.89	w = 1/[σ²(F_o²) + (0.0795P)²] where P = (F_o² + 2F_c²)/3
5986 reflections	(Δ/σ)_max = 0.001
390 parameters	Δρ_max = 0.55 e Å⁻³
0 restraints	Δρ_min = −0.81 e Å⁻³

Crystal data top

(C₁₄H₁₃N₂)[Fe(C₇H₃NO₄)₂]·2H₂O	V = 2602.1 (7) Å³
M_r = 631.35	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.9535 (14) Å	µ = 0.65 mm⁻¹
b = 18.607 (3) Å	T = 150 K
c = 15.674 (2) Å	0.50 × 0.40 × 0.08 mm
β = 94.826 (3)°

Data collection top

Bruker SMART diffractometer	5986 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	2776 reflections with I > 2σ(I)
T_min = 0.737, T_max = 0.950	R_int = 0.127
29654 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.165	H-atom parameters constrained
S = 0.89	Δρ_max = 0.55 e Å⁻³
5986 reflections	Δρ_min = −0.81 e Å⁻³
390 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Fe1	0.00816 (6)	0.59166 (3)	0.79981 (3)	0.03083 (19)
N1	0.0103 (3)	0.59937 (17)	0.66923 (19)	0.0271 (7)
N2	0.0118 (3)	0.60327 (17)	0.93011 (19)	0.0290 (8)
N3	0.1130 (3)	0.85237 (17)	1.1817 (2)	0.0308 (8)
H3A	0.1723	0.8278	1.2255	0.037*
N4	0.3022 (3)	0.74239 (18)	1.1490 (2)	0.0337 (8)
O1	0.1666 (3)	0.66723 (15)	0.78243 (16)	0.0374 (7)
O2	0.2907 (3)	0.72973 (16)	0.68816 (17)	0.0453 (8)
O3	−0.2573 (3)	0.46501 (16)	0.63913 (18)	0.0467 (8)
O4	−0.1384 (3)	0.51698 (14)	0.75482 (16)	0.0351 (7)
O5	0.1630 (3)	0.52142 (15)	0.84458 (17)	0.0382 (7)
O6	0.2980 (3)	0.47772 (17)	0.9602 (2)	0.0555 (9)
O7	−0.2787 (3)	0.72774 (17)	0.91050 (18)	0.0516 (9)
O8	−0.1594 (3)	0.66250 (15)	0.81730 (16)	0.0390 (7)
O9	0.1840 (3)	0.43660 (17)	0.69343 (19)	0.0573 (9)
H9B	0.1065	0.4021	0.6964	0.069*
H9A	0.1900	0.4509	0.7518	0.069*
O10	0.4860 (3)	0.80382 (17)	0.80094 (18)	0.0598 (9)
H10B	0.5093	0.8536	0.8009	0.072*
H10A	0.5375	0.7847	0.8514	0.072*
C1	0.1945 (4)	0.6862 (2)	0.7062 (3)	0.0352 (10)
C2	0.0991 (4)	0.6478 (2)	0.6361 (2)	0.0295 (9)
C3	0.0992 (4)	0.6569 (2)	0.5490 (2)	0.0361 (10)
H3	0.1638	0.6907	0.5256	0.043*
C4	0.0022 (4)	0.6152 (2)	0.4967 (3)	0.0377 (10)
H4	−0.0015	0.6203	0.4363	0.045*
C5	−0.0902 (4)	0.5654 (2)	0.5332 (3)	0.0349 (10)
H5	−0.1581	0.5368	0.4979	0.042*
C6	−0.0822 (4)	0.5584 (2)	0.6199 (2)	0.0294 (9)
C7	−0.1676 (4)	0.5071 (2)	0.6735 (3)	0.0335 (10)
C8	0.2013 (4)	0.5167 (2)	0.9265 (3)	0.0356 (10)
C9	0.1112 (4)	0.5660 (2)	0.9794 (3)	0.0311 (9)
C10	0.1242 (5)	0.5746 (2)	1.0666 (3)	0.0384 (11)
H10	0.1962	0.5482	1.1020	0.046*
C11	0.0282 (5)	0.6232 (2)	1.1014 (3)	0.0416 (11)
H11	0.0336	0.6296	1.1617	0.050*
C12	−0.0744 (5)	0.6620 (2)	1.0500 (2)	0.0382 (11)
H12	−0.1390	0.6956	1.0739	0.046*
C13	−0.0806 (4)	0.6508 (2)	0.9628 (2)	0.0328 (10)
C14	−0.1835 (4)	0.6849 (2)	0.8936 (3)	0.0357 (10)
C15	0.0199 (5)	0.9230 (3)	1.2958 (3)	0.0496 (13)
H15C	0.0366	0.8793	1.3304	0.074*
H15B	−0.0775	0.9438	1.3062	0.074*
H15A	0.0994	0.9578	1.3118	0.074*
C16	0.0215 (4)	0.9047 (2)	1.2041 (3)	0.0404 (11)
C17	−0.0667 (5)	0.9402 (2)	1.1396 (3)	0.0454 (12)
H17	−0.1329	0.9774	1.1539	0.054*
C18	−0.0577 (4)	0.9213 (2)	1.0562 (3)	0.0457 (12)
H18	−0.1187	0.9456	1.0128	0.055*
C19	0.0387 (4)	0.8672 (2)	1.0329 (3)	0.0359 (10)
C20	0.0586 (5)	0.8467 (2)	0.9465 (3)	0.0442 (11)
H20	0.0003	0.8696	0.9009	0.053*
C21	0.1576 (5)	0.7959 (2)	0.9285 (3)	0.0428 (11)
H21	0.1706	0.7845	0.8705	0.051*
C22	0.2434 (4)	0.7591 (2)	0.9956 (3)	0.0358 (10)
C23	0.3494 (5)	0.7056 (2)	0.9805 (3)	0.0397 (11)
H23	0.3669	0.6928	0.9235	0.048*
C24	0.4261 (5)	0.6725 (2)	1.0473 (3)	0.0429 (11)
H24	0.4982	0.6367	1.0373	0.052*
C25	0.3988 (4)	0.6913 (2)	1.1322 (3)	0.0390 (11)
C26	0.4740 (5)	0.6527 (3)	1.2077 (3)	0.0553 (13)
H26C	0.4998	0.6871	1.2539	0.083*
H26B	0.5655	0.6295	1.1911	0.083*
H26A	0.4061	0.6162	1.2275	0.083*
C27	0.2274 (4)	0.7761 (2)	1.0811 (2)	0.0323 (9)
C28	0.1244 (4)	0.8313 (2)	1.0993 (2)	0.0321 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.0346 (3)	0.0349 (4)	0.0232 (3)	−0.0007 (3)	0.0037 (2)	−0.0011 (3)
N1	0.0287 (17)	0.0283 (19)	0.0244 (16)	0.0021 (15)	0.0027 (13)	−0.0016 (15)
N2	0.0318 (18)	0.032 (2)	0.0233 (17)	−0.0043 (15)	0.0002 (14)	−0.0010 (15)
N3	0.0239 (17)	0.036 (2)	0.0317 (19)	−0.0033 (15)	−0.0006 (14)	0.0042 (16)
N4	0.0345 (19)	0.034 (2)	0.0315 (19)	−0.0059 (16)	−0.0070 (15)	−0.0004 (16)
O1	0.0468 (17)	0.0402 (18)	0.0247 (15)	−0.0065 (14)	−0.0004 (12)	−0.0026 (13)
O2	0.0473 (18)	0.046 (2)	0.0425 (18)	−0.0196 (16)	0.0046 (14)	0.0031 (15)
O3	0.0488 (19)	0.044 (2)	0.0463 (19)	−0.0172 (16)	−0.0025 (15)	−0.0075 (16)
O4	0.0382 (16)	0.0403 (18)	0.0271 (15)	−0.0050 (13)	0.0042 (12)	0.0022 (13)
O5	0.0404 (17)	0.0379 (18)	0.0368 (17)	0.0023 (14)	0.0058 (13)	−0.0042 (14)
O6	0.053 (2)	0.052 (2)	0.059 (2)	0.0143 (17)	−0.0112 (16)	0.0048 (17)
O7	0.0519 (19)	0.054 (2)	0.049 (2)	0.0192 (17)	0.0067 (15)	−0.0050 (17)
O8	0.0437 (17)	0.0455 (19)	0.0271 (16)	0.0076 (14)	−0.0010 (13)	−0.0008 (14)
O9	0.069 (2)	0.054 (2)	0.050 (2)	−0.0097 (18)	0.0111 (17)	−0.0099 (17)
O10	0.084 (3)	0.042 (2)	0.050 (2)	0.0052 (18)	−0.0086 (18)	−0.0004 (17)
C1	0.035 (2)	0.031 (3)	0.039 (3)	0.004 (2)	0.0014 (19)	0.003 (2)
C2	0.029 (2)	0.029 (2)	0.031 (2)	0.0010 (18)	0.0052 (17)	0.0006 (19)
C3	0.040 (2)	0.036 (3)	0.034 (2)	0.002 (2)	0.0096 (19)	0.008 (2)
C4	0.047 (3)	0.040 (3)	0.026 (2)	0.010 (2)	0.0002 (19)	0.000 (2)
C5	0.038 (2)	0.031 (2)	0.035 (2)	0.0081 (19)	−0.0026 (19)	−0.005 (2)
C6	0.028 (2)	0.028 (2)	0.032 (2)	0.0048 (18)	0.0011 (17)	−0.0052 (19)
C7	0.034 (2)	0.034 (3)	0.033 (2)	0.005 (2)	0.0022 (18)	0.000 (2)
C8	0.031 (2)	0.035 (3)	0.040 (3)	−0.008 (2)	0.0027 (19)	0.000 (2)
C9	0.034 (2)	0.029 (2)	0.031 (2)	−0.0057 (18)	0.0021 (18)	0.0056 (19)
C10	0.043 (3)	0.041 (3)	0.030 (2)	−0.015 (2)	−0.0042 (19)	0.006 (2)
C11	0.056 (3)	0.047 (3)	0.021 (2)	−0.021 (2)	0.002 (2)	−0.003 (2)
C12	0.044 (3)	0.040 (3)	0.032 (2)	−0.008 (2)	0.007 (2)	−0.010 (2)
C13	0.034 (2)	0.033 (3)	0.032 (2)	−0.0094 (19)	0.0051 (18)	−0.001 (2)
C14	0.037 (2)	0.034 (3)	0.036 (3)	0.002 (2)	0.0032 (19)	−0.001 (2)
C15	0.041 (3)	0.060 (3)	0.049 (3)	0.003 (2)	0.015 (2)	−0.011 (3)
C16	0.027 (2)	0.045 (3)	0.050 (3)	−0.006 (2)	0.008 (2)	−0.003 (2)
C17	0.029 (2)	0.044 (3)	0.063 (3)	0.002 (2)	0.005 (2)	0.000 (3)
C18	0.030 (2)	0.044 (3)	0.062 (3)	0.000 (2)	−0.004 (2)	0.012 (3)
C19	0.028 (2)	0.036 (3)	0.043 (3)	−0.0035 (19)	−0.0033 (18)	0.006 (2)
C20	0.053 (3)	0.045 (3)	0.032 (3)	−0.001 (2)	−0.013 (2)	0.007 (2)
C21	0.058 (3)	0.041 (3)	0.029 (2)	−0.007 (2)	−0.002 (2)	0.002 (2)
C22	0.040 (2)	0.034 (3)	0.034 (2)	−0.010 (2)	0.0036 (19)	−0.003 (2)
C23	0.046 (3)	0.039 (3)	0.035 (3)	−0.010 (2)	0.009 (2)	−0.004 (2)
C24	0.044 (3)	0.034 (3)	0.051 (3)	−0.002 (2)	0.008 (2)	−0.004 (2)
C25	0.036 (2)	0.035 (3)	0.044 (3)	−0.005 (2)	−0.006 (2)	0.001 (2)
C26	0.062 (3)	0.045 (3)	0.057 (3)	0.009 (3)	−0.007 (2)	0.004 (3)
C27	0.030 (2)	0.031 (2)	0.035 (2)	−0.0062 (19)	0.0004 (17)	−0.001 (2)
C28	0.030 (2)	0.034 (3)	0.032 (2)	−0.0071 (19)	0.0009 (17)	0.0021 (19)

Geometric parameters (Å, º) top

Fe1—O5	1.990 (3)	C8—C9	1.514 (5)
Fe1—O4	1.999 (3)	C9—C10	1.371 (5)
Fe1—O1	2.032 (3)	C10—C11	1.390 (6)
Fe1—O8	2.033 (3)	C10—H10	0.9500
Fe1—N2	2.051 (3)	C11—C12	1.375 (5)
Fe1—N1	2.054 (3)	C11—H11	0.9500
N1—C6	1.325 (5)	C12—C13	1.379 (5)
N1—C2	1.335 (4)	C12—H12	0.9500
N2—C9	1.325 (5)	C13—C14	1.503 (5)
N2—C13	1.342 (5)	C15—C16	1.479 (5)
N3—C16	1.338 (5)	C15—H15C	0.9800
N3—C28	1.362 (5)	C15—H15B	0.9800
N3—H3A	0.9501	C15—H15A	0.9800
N4—C25	1.326 (5)	C16—C17	1.395 (6)
N4—C27	1.362 (5)	C17—C18	1.363 (6)
O1—C1	1.290 (4)	C17—H17	0.9500
O2—C1	1.232 (5)	C18—C19	1.395 (6)
O3—C7	1.216 (4)	C18—H18	0.9500
O4—C7	1.292 (4)	C19—C28	1.408 (5)
O5—C8	1.303 (4)	C19—C20	1.432 (5)
O6—C8	1.215 (5)	C20—C21	1.341 (6)
O7—C14	1.213 (4)	C20—H20	0.9500
O8—C14	1.301 (4)	C21—C22	1.424 (6)
O9—H9B	0.9499	C21—H21	0.9500
O9—H9A	0.9497	C22—C27	1.396 (5)
O10—H10B	0.9500	C22—C23	1.409 (5)
O10—H10A	0.9502	C23—C24	1.351 (6)
C1—C2	1.514 (5)	C23—H23	0.9500
C2—C3	1.375 (5)	C24—C25	1.418 (6)
C3—C4	1.381 (5)	C24—H24	0.9500
C3—H3	0.9500	C25—C26	1.494 (6)
C4—C5	1.396 (5)	C26—H26C	0.9800
C4—H4	0.9500	C26—H26B	0.9800
C5—C6	1.361 (5)	C26—H26A	0.9800
C5—H5	0.9500	C27—C28	1.426 (5)
C6—C7	1.520 (5)

O5—Fe1—O4	94.88 (11)	C12—C11—C10	121.1 (4)
O5—Fe1—O1	91.61 (11)	C12—C11—H11	119.4
O4—Fe1—O1	151.51 (10)	C10—C11—H11	119.4
O5—Fe1—O8	151.48 (11)	C11—C12—C13	118.0 (4)
O4—Fe1—O8	91.63 (11)	C11—C12—H12	121.0
O1—Fe1—O8	95.78 (12)	C13—C12—H12	121.0
O5—Fe1—N2	76.47 (12)	N2—C13—C12	120.2 (4)
O4—Fe1—N2	112.29 (11)	N2—C13—C14	111.3 (3)
O1—Fe1—N2	96.20 (11)	C12—C13—C14	128.5 (4)
O8—Fe1—N2	75.37 (12)	O7—C14—O8	125.8 (4)
O5—Fe1—N1	109.44 (11)	O7—C14—C13	121.3 (4)
O4—Fe1—N1	75.98 (11)	O8—C14—C13	112.9 (3)
O1—Fe1—N1	75.70 (11)	C16—C15—H15C	109.5
O8—Fe1—N1	99.08 (11)	C16—C15—H15B	109.5
N2—Fe1—N1	169.85 (12)	H15C—C15—H15B	109.5
C6—N1—C2	121.6 (3)	C16—C15—H15A	109.5
C6—N1—Fe1	118.9 (3)	H15C—C15—H15A	109.5
C2—N1—Fe1	119.4 (3)	H15B—C15—H15A	109.5
C9—N2—C13	121.9 (3)	N3—C16—C17	118.5 (4)
C9—N2—Fe1	118.6 (3)	N3—C16—C15	118.6 (4)
C13—N2—Fe1	119.4 (3)	C17—C16—C15	123.0 (4)
C16—N3—C28	123.7 (4)	C18—C17—C16	119.8 (4)
C16—N3—H3A	118.6	C18—C17—H17	120.1
C28—N3—H3A	117.7	C16—C17—H17	120.1
C25—N4—C27	117.5 (3)	C17—C18—C19	121.7 (4)
C1—O1—Fe1	120.4 (3)	C17—C18—H18	119.1
C7—O4—Fe1	121.3 (3)	C19—C18—H18	119.1
C8—O5—Fe1	120.6 (3)	C18—C19—C28	117.3 (4)
C14—O8—Fe1	120.9 (3)	C18—C19—C20	124.7 (4)
H9B—O9—H9A	97.1	C28—C19—C20	118.0 (4)
H10B—O10—H10A	105.9	C21—C20—C19	121.6 (4)
O2—C1—O1	125.9 (4)	C21—C20—H20	119.2
O2—C1—C2	120.4 (4)	C19—C20—H20	119.2
O1—C1—C2	113.7 (3)	C20—C21—C22	120.5 (4)
N1—C2—C3	121.3 (4)	C20—C21—H21	119.7
N1—C2—C1	110.7 (3)	C22—C21—H21	119.7
C3—C2—C1	127.9 (4)	C27—C22—C23	116.5 (4)
C2—C3—C4	117.8 (4)	C27—C22—C21	120.5 (4)
C2—C3—H3	121.1	C23—C22—C21	123.0 (4)
C4—C3—H3	121.1	C24—C23—C22	119.8 (4)
C3—C4—C5	119.6 (4)	C24—C23—H23	120.1
C3—C4—H4	120.2	C22—C23—H23	120.1
C5—C4—H4	120.2	C23—C24—C25	119.9 (4)
C6—C5—C4	119.3 (4)	C23—C24—H24	120.0
C6—C5—H5	120.4	C25—C24—H24	120.0
C4—C5—H5	120.4	N4—C25—C24	122.0 (4)
N1—C6—C5	120.4 (4)	N4—C25—C26	116.5 (4)
N1—C6—C7	110.9 (3)	C24—C25—C26	121.5 (4)
C5—C6—C7	128.7 (4)	C25—C26—H26C	109.5
O3—C7—O4	126.9 (4)	C25—C26—H26B	109.5
O3—C7—C6	120.2 (4)	H26C—C26—H26B	109.5
O4—C7—C6	112.8 (4)	C25—C26—H26A	109.5
O6—C8—O5	126.0 (4)	H26C—C26—H26A	109.5
O6—C8—C9	121.0 (4)	H26B—C26—H26A	109.5
O5—C8—C9	113.0 (4)	N4—C27—C22	124.3 (4)
N2—C9—C10	121.1 (4)	N4—C27—C28	117.3 (4)
N2—C9—C8	111.1 (3)	C22—C27—C28	118.4 (4)
C10—C9—C8	127.8 (4)	N3—C28—C19	119.0 (4)
C9—C10—C11	117.6 (4)	N3—C28—C27	119.9 (4)
C9—C10—H10	121.2	C19—C28—C27	121.0 (4)
C11—C10—H10	121.2

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O9—H9B···O10ⁱ	0.95	2.01	2.907 (5)	157
O9—H9A···O5	0.95	1.99	2.866 (4)	153
O10—H10B···O9ⁱⁱ	0.95	2.33	2.907 (4)	119
O10—H10A···O7ⁱⁱⁱ	0.95	2.11	2.964 (4)	150
N3—H3A···O8^iv	0.95	2.00	2.832 (4)	145
C3—H3···O7^v	0.95	2.45	3.304 (5)	150
C12—H12···O2^vi	0.95	2.39	3.263 (5)	152
C17—H17···O9^vi	0.95	2.41	3.357 (5)	175

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

Experimental details

Crystal data
Chemical formula	(C₁₄H₁₃N₂)[Fe(C₇H₃NO₄)₂]·2H₂O
M_r	631.35
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	150
a, b, c (Å)	8.9535 (14), 18.607 (3), 15.674 (2)
β (°)	94.826 (3)
V (Å³)	2602.1 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.65
Crystal size (mm)	0.50 × 0.40 × 0.08

Data collection
Diffractometer	Bruker SMART
Absorption correction	Multi-scan (SADABS; Sheldrick, 1998)
T_min, T_max	0.737, 0.950
No. of measured, independent and observed [I > 2σ(I)] reflections	29654, 5986, 2776
R_int	0.127
(sin θ/λ)_max (Å⁻¹)	0.653

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.165, 0.89
No. of reflections	5986
No. of parameters	390
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.55, −0.81

Computer programs: SMART (Bruker, 1998), SAINT-Plus (Bruker, 1998), SAINT-Plus, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1998), SHELXTL.