(Methanolato)(pyridine)[N2,N2′-(pyridine-2,6-diyldicarbon­yl)diacetohydra­zide(2–)]iron(III) methanol solvate

Cao, Q.-F.; Dou, J.-M.; Li, D.-C.; Wang, D.-Q.

doi:10.1107/S1600536807060862

(Methanolato)(pyridine)[N²,N^2′-(pyridine-2,6-diyldicarbonyl)diacetohydrazide(2–)]iron(III) methanol solvate

Q.-F. Cao, J.-M. Dou, D.-C. Li and D.-Q. Wang

In the title complex, [Fe(C₁₁H₁₀N₅O₄)(CH₃O)(C₅H₅N)]·CH₄O, the Fe^III ion has a distorted pentagonal-bipyramidal geometry. In the crystal structure, molecules are linked into one-dimensional chains along [1 $\overline{1}$ $\overline{1}$ ] via intermolecular O—H

O and N—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807060862/lh2566sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807060862/lh2566Isup2.hkl Contains datablock I

CCDC reference: 654349

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Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.006 Å
R factor = 0.044
wR factor = 0.115
Data-to-parameter ratio = 12.8

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Alert level C
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          3

   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
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
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Comment top

Metal-hydrazide complexes, especially Fe complexes with acetylhydrazide, continue to attract considerable attention due to their biological activities and structural versatilities (Drozdzewski et al., 2006; Sreeja et al., 2004) We report herein, the crystal structure of the title complex. A view of the title complex (I) is shown in Fig.1. The Fe^III ion has a distorted pentagonal-bipyramidal coordination geometry, formed by one 2-oxido-N, N'-2,6-picoloylhydrazide ligand, one pyridine ligand and one methanol molecule. The distances involving atom Fe1 atom are consistent with those in a Fe complex with pentagonal-bipyramidal coordination geometry (Bonardi et al., 1991). Both intermolecular O—H···O and N—H···O hydrogen bonding occur in the crystal structure (Table 2).

Related literature top

For related literature, see: Sreeja et al. (2004); Bonardi et al. (1991); Drozdzewski et al. (2006).

Experimental top

A pyridine solution (10 mL) of N,N'-diacetyl-2,6-picoloylhydrazide (0.2 mmol,0.0559 g) was mixed with a methanol solution (10 mL) of iron chloride (0.2 mmol, 0.0808 g). The mixture was stirred at room temperature for 6 h and then filtered. Dark block-shaped crystals of the title complex suitable for X-ray diffraction analysis were obtained after three weeks (m.p. >573 K). Elemental analysis calculated for (C₁₈H₂₃N₆O₆)Fe: C 45.49, H 4.88, N 17.68%; found: C 45.41, H 4.76, N 17.50%.

Structure description top

For related literature, see: Sreeja et al. (2004); Bonardi et al. (1991); Drozdzewski et al. (2006).

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title complex. Displacement ellipsoids are drawn at 30% probability level and solvent molecule has been omitted for clarity.
	Fig. 2. Part of the crystal structure with hydrogen bonds shown as dashed lines.

(Methanolato)(pyridine)[N²,N^2'-(pyridine-2,6- diyldicarbonyl)diacetohydrazide(2-)]iron(III) methanol solvate top

Crystal data top

[Fe(C₁₁H₁₀N₅O₄)(CH₃O)(C₅H₅N)]·CH₄O	Z = 2
M_r = 475.27	F(000) = 494
Triclinic, P1	D_x = 1.491 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.258 (10) Å	Cell parameters from 1856 reflections
b = 10.64 (14) Å	θ = 2.4–25.1°
c = 12.448 (18) Å	µ = 0.76 mm⁻¹
α = 83.518 (3)°	T = 298 K
β = 85.924 (3)°	Block, black
γ = 77.176 (2)°	0.37 × 0.29 × 0.20 mm
V = 1058.4 (2) Å³

Data collection top

Siemens SMART CCD area-detector diffractometer	3658 independent reflections
Radiation source: fine-focus sealed tube	2647 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
φ and ω scans	θ_max = 25.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.766, T_max = 0.863	k = −12→9
5507 measured reflections	l = −14→14

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) = 0.115	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.050P)² + 0.8457P] where P = (F_o² + 2F_c²)/3
3658 reflections	(Δ/σ)_max = 0.004
285 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

[Fe(C₁₁H₁₀N₅O₄)(CH₃O)(C₅H₅N)]·CH₄O	γ = 77.176 (2)°
M_r = 475.27	V = 1058.4 (2) Å³
Triclinic, P1	Z = 2
a = 8.258 (10) Å	Mo Kα radiation
b = 10.64 (14) Å	µ = 0.76 mm⁻¹
c = 12.448 (18) Å	T = 298 K
α = 83.518 (3)°	0.37 × 0.29 × 0.20 mm
β = 85.924 (3)°

Data collection top

Siemens SMART CCD area-detector diffractometer	3658 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2647 reflections with I > 2σ(I)
T_min = 0.766, T_max = 0.863	R_int = 0.021
5507 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.115	H-atom parameters constrained
S = 1.00	Δρ_max = 0.45 e Å⁻³
3658 reflections	Δρ_min = −0.27 e Å⁻³
285 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	0.31969 (6)	0.23928 (4)	0.23357 (4)	0.03344 (18)
N1	0.2243 (3)	0.4328 (2)	0.1451 (2)	0.0303 (6)
N2	0.1580 (4)	0.3649 (2)	0.3383 (2)	0.0338 (7)
N3	0.1451 (4)	0.3167 (3)	0.4458 (2)	0.0384 (7)
H3	0.0928	0.3633	0.4949	0.046*
N4	0.4403 (4)	0.2535 (3)	0.0791 (2)	0.0370 (7)
N5	0.5609 (4)	0.1455 (3)	0.0544 (2)	0.0423 (8)
H5	0.6117	0.1395	−0.0082	0.051*
N6	0.5139 (4)	0.3108 (3)	0.3122 (2)	0.0391 (7)
O1	0.0049 (3)	0.5677 (2)	0.37219 (18)	0.0445 (7)
O2	0.4513 (4)	0.3481 (2)	−0.0965 (2)	0.0585 (8)
O3	0.2966 (3)	0.1301 (2)	0.39371 (18)	0.0441 (7)
O4	0.5115 (3)	0.0678 (2)	0.22480 (18)	0.0427 (6)
O5	0.1500 (3)	0.1644 (2)	0.18472 (19)	0.0420 (6)
O6	0.7483 (4)	0.0858 (3)	0.8604 (2)	0.0673 (9)
H6	0.7754	0.0083	0.8528	0.101*
C1	0.0853 (4)	0.4869 (3)	0.3119 (3)	0.0309 (8)
C2	0.1142 (4)	0.5230 (3)	0.1937 (3)	0.0329 (8)
C3	0.0382 (5)	0.6368 (3)	0.1377 (3)	0.0466 (10)
H3A	−0.0392	0.6984	0.1725	0.056*
C4	0.0788 (5)	0.6583 (4)	0.0286 (3)	0.0543 (12)
H4	0.0276	0.7342	−0.0112	0.065*
C5	0.1959 (5)	0.5662 (3)	−0.0208 (3)	0.0473 (10)
H5A	0.2262	0.5796	−0.0939	0.057*
C6	0.2669 (4)	0.4542 (3)	0.0403 (3)	0.0331 (8)
C7	0.3972 (5)	0.3455 (3)	−0.0011 (3)	0.0374 (9)
C8	0.2196 (5)	0.1930 (3)	0.4677 (3)	0.0412 (9)
C9	0.2090 (6)	0.1342 (4)	0.5816 (3)	0.0655 (14)
H9A	0.1532	0.0636	0.5849	0.098*
H9B	0.1479	0.1984	0.6262	0.098*
H9C	0.3190	0.1026	0.6072	0.098*
C10	0.5907 (5)	0.0531 (3)	0.1351 (3)	0.0394 (9)
C11	0.7196 (5)	−0.0667 (4)	0.1174 (3)	0.0561 (12)
H11A	0.8101	−0.0731	0.1634	0.084*
H11B	0.7600	−0.0628	0.0431	0.084*
H11C	0.6714	−0.1413	0.1341	0.084*
C12	0.5929 (5)	0.2396 (4)	0.3965 (3)	0.0560 (11)
H12	0.5816	0.1544	0.4128	0.067*
C13	0.6902 (6)	0.2880 (6)	0.4597 (4)	0.0707 (14)
H13	0.7425	0.2363	0.5180	0.085*
C14	0.7092 (6)	0.4122 (6)	0.4364 (4)	0.0709 (14)
H14	0.7723	0.4472	0.4792	0.085*
C15	0.6335 (6)	0.4841 (5)	0.3486 (4)	0.0683 (13)
H15	0.6469	0.5684	0.3295	0.082*
C16	0.5374 (5)	0.4305 (4)	0.2890 (3)	0.0503 (10)
H16	0.4863	0.4804	0.2295	0.060*
C17	−0.0016 (6)	0.1640 (4)	0.2357 (4)	0.0607 (12)
H17A	0.0131	0.1184	0.3066	0.091*
H17B	−0.0639	0.1218	0.1945	0.091*
H17C	−0.0607	0.2516	0.2419	0.091*
C18	0.7218 (7)	0.1580 (4)	0.7573 (4)	0.0744 (15)
H18A	0.6765	0.2475	0.7668	0.112*
H18B	0.6454	0.1248	0.7195	0.112*
H18C	0.8257	0.1503	0.7160	0.112*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.0429 (3)	0.0265 (3)	0.0255 (3)	0.0037 (2)	0.0005 (2)	−0.00328 (19)
N1	0.0369 (17)	0.0263 (14)	0.0241 (14)	0.0012 (12)	−0.0014 (12)	−0.0032 (11)
N2	0.0463 (18)	0.0276 (15)	0.0221 (14)	0.0017 (13)	0.0010 (13)	−0.0003 (11)
N3	0.055 (2)	0.0319 (16)	0.0214 (14)	0.0048 (14)	0.0045 (13)	−0.0049 (12)
N4	0.0420 (18)	0.0321 (16)	0.0287 (15)	0.0084 (13)	0.0021 (13)	−0.0035 (13)
N5	0.052 (2)	0.0353 (17)	0.0294 (16)	0.0109 (14)	0.0068 (14)	−0.0068 (13)
N6	0.0381 (18)	0.0389 (17)	0.0360 (17)	0.0006 (14)	−0.0005 (14)	−0.0041 (14)
O1	0.0584 (17)	0.0358 (14)	0.0310 (13)	0.0083 (12)	0.0053 (12)	−0.0092 (11)
O2	0.082 (2)	0.0459 (16)	0.0315 (15)	0.0122 (14)	0.0145 (14)	0.0010 (12)
O3	0.0611 (18)	0.0313 (13)	0.0317 (14)	0.0057 (12)	0.0040 (12)	−0.0034 (11)
O4	0.0538 (17)	0.0333 (13)	0.0307 (14)	0.0099 (11)	0.0010 (12)	−0.0005 (11)
O5	0.0567 (18)	0.0337 (14)	0.0334 (14)	−0.0041 (12)	−0.0006 (12)	−0.0066 (11)
O6	0.099 (3)	0.0498 (17)	0.0482 (18)	−0.0039 (17)	0.0139 (16)	−0.0173 (14)
C1	0.0318 (19)	0.0311 (18)	0.0282 (18)	−0.0018 (15)	−0.0008 (15)	−0.0066 (15)
C2	0.039 (2)	0.0291 (18)	0.0282 (18)	−0.0007 (15)	−0.0013 (15)	−0.0071 (14)
C3	0.062 (3)	0.033 (2)	0.034 (2)	0.0134 (18)	0.0006 (18)	−0.0034 (16)
C4	0.074 (3)	0.035 (2)	0.039 (2)	0.014 (2)	−0.002 (2)	0.0081 (17)
C5	0.064 (3)	0.041 (2)	0.0274 (19)	0.0053 (19)	0.0002 (18)	0.0015 (16)
C6	0.040 (2)	0.0290 (18)	0.0276 (18)	−0.0014 (15)	−0.0028 (15)	−0.0009 (14)
C7	0.046 (2)	0.0310 (19)	0.0296 (19)	0.0016 (16)	0.0031 (16)	−0.0030 (15)
C8	0.054 (2)	0.035 (2)	0.0306 (19)	−0.0005 (17)	−0.0002 (17)	−0.0015 (16)
C9	0.099 (4)	0.048 (2)	0.034 (2)	0.008 (2)	0.011 (2)	0.0040 (19)
C10	0.048 (2)	0.0324 (19)	0.031 (2)	0.0069 (16)	−0.0005 (17)	−0.0080 (16)
C11	0.067 (3)	0.044 (2)	0.043 (2)	0.020 (2)	−0.002 (2)	−0.0077 (18)
C12	0.050 (3)	0.060 (3)	0.052 (3)	−0.003 (2)	−0.012 (2)	0.008 (2)
C13	0.055 (3)	0.102 (4)	0.053 (3)	−0.014 (3)	−0.020 (2)	0.008 (3)
C14	0.060 (3)	0.101 (4)	0.062 (3)	−0.030 (3)	−0.006 (3)	−0.020 (3)
C15	0.061 (3)	0.065 (3)	0.086 (4)	−0.026 (2)	−0.011 (3)	−0.010 (3)
C16	0.044 (2)	0.051 (3)	0.055 (3)	−0.0125 (19)	−0.003 (2)	0.005 (2)
C17	0.067 (3)	0.058 (3)	0.058 (3)	−0.014 (2)	−0.005 (2)	−0.006 (2)
C18	0.109 (4)	0.053 (3)	0.057 (3)	−0.015 (3)	0.021 (3)	−0.007 (2)

Geometric parameters (Å, º) top

Fe1—O5	1.922 (3)	C3—H3A	0.9300
Fe1—N4	2.107 (3)	C4—C5	1.381 (5)
Fe1—O4	2.142 (2)	C4—H4	0.9300
Fe1—N2	2.150 (3)	C5—C6	1.375 (5)
Fe1—O3	2.209 (2)	C5—H5A	0.9300
Fe1—N1	2.228 (3)	C6—C7	1.505 (4)
Fe1—N6	2.245 (3)	C8—C9	1.489 (5)
N1—C2	1.334 (4)	C9—H9A	0.9600
N1—C6	1.334 (4)	C9—H9B	0.9600
N2—C1	1.319 (4)	C9—H9C	0.9600
N2—N3	1.384 (4)	C10—C11	1.495 (5)
N3—C8	1.330 (4)	C11—H11A	0.9600
N3—H3	0.8600	C11—H11B	0.9600
N4—C7	1.325 (4)	C11—H11C	0.9600
N4—N5	1.391 (4)	C12—C13	1.377 (6)
N5—C10	1.320 (4)	C12—H12	0.9300
N5—H5	0.8600	C13—C14	1.361 (7)
N6—C16	1.327 (5)	C13—H13	0.9300
N6—C12	1.341 (4)	C14—C15	1.366 (6)
O1—C1	1.251 (4)	C14—H14	0.9300
O2—C7	1.238 (4)	C15—C16	1.374 (6)
O3—C8	1.252 (4)	C15—H15	0.9300
O4—C10	1.260 (4)	C16—H16	0.9300
O5—C17	1.363 (5)	C17—H17A	0.9600
O6—C18	1.424 (5)	C17—H17B	0.9600
O6—H6	0.8200	C17—H17C	0.9600
C1—C2	1.494 (4)	C18—H18A	0.9600
C2—C3	1.372 (5)	C18—H18B	0.9600
C3—C4	1.381 (5)	C18—H18C	0.9600

O5—Fe1—N4	93.67 (11)	C6—C5—C4	118.6 (3)
O5—Fe1—O4	94.66 (10)	C6—C5—H5A	120.7
N4—Fe1—O4	72.86 (9)	C4—C5—H5A	120.7
O5—Fe1—N2	96.21 (11)	N1—C6—C5	121.5 (3)
N4—Fe1—N2	138.16 (10)	N1—C6—C7	113.4 (3)
O4—Fe1—N2	145.91 (10)	C5—C6—C7	125.1 (3)
O5—Fe1—O3	88.85 (10)	O2—C7—N4	128.1 (3)
N4—Fe1—O3	149.43 (10)	O2—C7—C6	122.4 (3)
O4—Fe1—O3	76.57 (9)	N4—C7—C6	109.5 (3)
N2—Fe1—O3	71.46 (9)	O3—C8—N3	120.0 (3)
O5—Fe1—N1	93.58 (10)	O3—C8—C9	122.1 (3)
N4—Fe1—N1	69.58 (10)	N3—C8—C9	117.9 (3)
O4—Fe1—N1	141.95 (10)	C8—C9—H9A	109.5
N2—Fe1—N1	69.30 (10)	C8—C9—H9B	109.5
O3—Fe1—N1	140.72 (9)	H9A—C9—H9B	109.5
O5—Fe1—N6	172.22 (11)	C8—C9—H9C	109.5
N4—Fe1—N6	92.96 (11)	H9A—C9—H9C	109.5
O4—Fe1—N6	83.42 (10)	H9B—C9—H9C	109.5
N2—Fe1—N6	81.48 (11)	O4—C10—N5	119.8 (3)
O3—Fe1—N6	83.37 (10)	O4—C10—C11	121.7 (3)
N1—Fe1—N6	92.54 (10)	N5—C10—C11	118.6 (3)
C2—N1—C6	120.0 (3)	C10—C11—H11A	109.5
C2—N1—Fe1	120.3 (2)	C10—C11—H11B	109.5
C6—N1—Fe1	119.5 (2)	H11A—C11—H11B	109.5
C1—N2—N3	117.5 (3)	C10—C11—H11C	109.5
C1—N2—Fe1	125.9 (2)	H11A—C11—H11C	109.5
N3—N2—Fe1	116.18 (18)	H11B—C11—H11C	109.5
C8—N3—N2	114.9 (3)	N6—C12—C13	122.4 (4)
C8—N3—H3	122.5	N6—C12—H12	118.8
N2—N3—H3	122.5	C13—C12—H12	118.8
C7—N4—N5	116.8 (3)	C14—C13—C12	119.6 (4)
C7—N4—Fe1	126.6 (2)	C14—C13—H13	120.2
N5—N4—Fe1	115.8 (2)	C12—C13—H13	120.2
C10—N5—N4	114.3 (3)	C13—C14—C15	118.5 (4)
C10—N5—H5	122.9	C13—C14—H14	120.8
N4—N5—H5	122.9	C15—C14—H14	120.8
C16—N6—C12	117.2 (4)	C14—C15—C16	119.2 (5)
C16—N6—Fe1	122.0 (3)	C14—C15—H15	120.4
C12—N6—Fe1	120.1 (3)	C16—C15—H15	120.4
C8—O3—Fe1	116.7 (2)	N6—C16—C15	123.2 (4)
C10—O4—Fe1	117.0 (2)	N6—C16—H16	118.4
C17—O5—Fe1	125.7 (2)	C15—C16—H16	118.4
C18—O6—H6	109.5	O5—C17—H17A	109.5
O1—C1—N2	128.4 (3)	O5—C17—H17B	109.5
O1—C1—C2	121.3 (3)	H17A—C17—H17B	109.5
N2—C1—C2	110.3 (3)	O5—C17—H17C	109.5
N1—C2—C3	121.6 (3)	H17A—C17—H17C	109.5
N1—C2—C1	113.5 (3)	H17B—C17—H17C	109.5
C3—C2—C1	125.0 (3)	O6—C18—H18A	109.5
C2—C3—C4	118.8 (3)	O6—C18—H18B	109.5
C2—C3—H3A	120.6	H18A—C18—H18B	109.5
C4—C3—H3A	120.6	O6—C18—H18C	109.5
C3—C4—C5	119.5 (3)	H18A—C18—H18C	109.5
C3—C4—H4	120.3	H18B—C18—H18C	109.5
C5—C4—H4	120.3

O5—Fe1—N1—C2	91.5 (3)	N4—Fe1—O4—C10	−5.2 (3)
N4—Fe1—N1—C2	−175.9 (3)	N2—Fe1—O4—C10	−164.4 (3)
O4—Fe1—N1—C2	−166.3 (2)	O3—Fe1—O4—C10	175.0 (3)
N2—Fe1—N1—C2	−3.8 (2)	N1—Fe1—O4—C10	−14.6 (4)
O3—Fe1—N1—C2	−1.1 (3)	N6—Fe1—O4—C10	−100.3 (3)
N6—Fe1—N1—C2	−83.7 (3)	N4—Fe1—O5—C17	−159.1 (3)
O5—Fe1—N1—C6	−82.8 (3)	O4—Fe1—O5—C17	127.8 (3)
N4—Fe1—N1—C6	9.8 (2)	N2—Fe1—O5—C17	−19.8 (3)
O4—Fe1—N1—C6	19.5 (3)	O3—Fe1—O5—C17	51.4 (3)
N2—Fe1—N1—C6	−178.1 (3)	N1—Fe1—O5—C17	−89.3 (3)
O3—Fe1—N1—C6	−175.3 (2)	N3—N2—C1—O1	0.5 (6)
N6—Fe1—N1—C6	102.0 (3)	Fe1—N2—C1—O1	−171.7 (3)
O5—Fe1—N2—C1	−93.7 (3)	N3—N2—C1—C2	179.0 (3)
N4—Fe1—N2—C1	8.9 (4)	Fe1—N2—C1—C2	6.8 (4)
O4—Fe1—N2—C1	158.5 (2)	C6—N1—C2—C3	2.2 (5)
O3—Fe1—N2—C1	179.6 (3)	Fe1—N1—C2—C3	−172.0 (3)
N1—Fe1—N2—C1	−2.2 (3)	C6—N1—C2—C1	−177.5 (3)
N6—Fe1—N2—C1	93.8 (3)	Fe1—N1—C2—C1	8.3 (4)
O5—Fe1—N2—N3	94.0 (2)	O1—C1—C2—N1	169.5 (3)
N4—Fe1—N2—N3	−163.4 (2)	N2—C1—C2—N1	−9.2 (4)
O4—Fe1—N2—N3	−13.9 (4)	O1—C1—C2—C3	−10.3 (6)
O3—Fe1—N2—N3	7.3 (2)	N2—C1—C2—C3	171.1 (4)
N1—Fe1—N2—N3	−174.5 (3)	N1—C2—C3—C4	−0.7 (6)
N6—Fe1—N2—N3	−78.5 (2)	C1—C2—C3—C4	179.0 (4)
C1—N2—N3—C8	179.5 (3)	C2—C3—C4—C5	−1.0 (6)
Fe1—N2—N3—C8	−7.5 (4)	C3—C4—C5—C6	1.1 (7)
O5—Fe1—N4—C7	81.0 (3)	C2—N1—C6—C5	−2.1 (5)
O4—Fe1—N4—C7	174.7 (3)	Fe1—N1—C6—C5	172.1 (3)
N2—Fe1—N4—C7	−22.6 (4)	C2—N1—C6—C7	177.7 (3)
O3—Fe1—N4—C7	174.9 (3)	Fe1—N1—C6—C7	−8.0 (4)
N1—Fe1—N4—C7	−11.5 (3)	C4—C5—C6—N1	0.4 (6)
N6—Fe1—N4—C7	−103.1 (3)	C4—C5—C6—C7	−179.4 (4)
O5—Fe1—N4—N5	−88.6 (2)	N5—N4—C7—O2	−0.2 (6)
O4—Fe1—N4—N5	5.1 (2)	Fe1—N4—C7—O2	−169.8 (3)
N2—Fe1—N4—N5	167.8 (2)	N5—N4—C7—C6	−179.7 (3)
O3—Fe1—N4—N5	5.3 (4)	Fe1—N4—C7—C6	10.7 (4)
N1—Fe1—N4—N5	178.9 (3)	N1—C6—C7—O2	179.6 (4)
N6—Fe1—N4—N5	87.3 (2)	C5—C6—C7—O2	−0.5 (6)
C7—N4—N5—C10	−175.5 (3)	N1—C6—C7—N4	−0.8 (4)
Fe1—N4—N5—C10	−4.8 (4)	C5—C6—C7—N4	179.0 (4)
N4—Fe1—N6—C16	65.6 (3)	Fe1—O3—C8—N3	5.4 (5)
O4—Fe1—N6—C16	138.0 (3)	Fe1—O3—C8—C9	−174.0 (3)
N2—Fe1—N6—C16	−72.7 (3)	N2—N3—C8—O3	1.3 (5)
O3—Fe1—N6—C16	−144.8 (3)	N2—N3—C8—C9	−179.3 (3)
N1—Fe1—N6—C16	−4.0 (3)	Fe1—O4—C10—N5	4.4 (5)
N4—Fe1—N6—C12	−124.6 (3)	Fe1—O4—C10—C11	−175.9 (3)
O4—Fe1—N6—C12	−52.3 (3)	N4—N5—C10—O4	0.2 (5)
N2—Fe1—N6—C12	97.1 (3)	N4—N5—C10—C11	−179.4 (3)
O3—Fe1—N6—C12	24.9 (3)	C16—N6—C12—C13	2.2 (6)
N1—Fe1—N6—C12	165.7 (3)	Fe1—N6—C12—C13	−168.0 (3)
O5—Fe1—O3—C8	−103.8 (3)	N6—C12—C13—C14	−0.5 (7)
N4—Fe1—O3—C8	161.0 (3)	C12—C13—C14—C15	−1.5 (7)
O4—Fe1—O3—C8	161.2 (3)	C13—C14—C15—C16	1.8 (7)
N2—Fe1—O3—C8	−6.8 (3)	C12—N6—C16—C15	−1.9 (6)
N1—Fe1—O3—C8	−9.5 (4)	Fe1—N6—C16—C15	168.1 (3)
N6—Fe1—O3—C8	76.4 (3)	C14—C15—C16—N6	−0.1 (7)
O5—Fe1—O4—C10	87.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1ⁱ	0.86	1.94	2.780 (3)	167
N5—H5···O6ⁱⁱ	0.86	1.98	2.830 (4)	167
O6—H6···O5ⁱⁱⁱ	0.82	1.90	2.718 (3)	172

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

Experimental details

Crystal data
Chemical formula	[Fe(C₁₁H₁₀N₅O₄)(CH₃O)(C₅H₅N)]·CH₄O
M_r	475.27
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	8.258 (10), 10.64 (14), 12.448 (18)
α, β, γ (°)	83.518 (3), 85.924 (3), 77.176 (2)
V (Å³)	1058.4 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.76
Crystal size (mm)	0.37 × 0.29 × 0.20

Data collection
Diffractometer	Siemens SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.766, 0.863
No. of measured, independent and observed [I > 2σ(I)] reflections	5507, 3658, 2647
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.115, 1.00
No. of reflections	3658
No. of parameters	285
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.27

Computer programs: SMART (Bruker, 1996), SAINT (Bruker, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).

Selected bond lengths (Å) top

Fe1—O5	1.922 (3)	Fe1—O3	2.209 (2)
Fe1—N4	2.107 (3)	Fe1—N1	2.228 (3)
Fe1—O4	2.142 (2)	Fe1—N6	2.245 (3)
Fe1—N2	2.150 (3)