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Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): m47.
Published online 2007 December 6. doi:  10.1107/S1600536807060862
PMCID: PMC2914931

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

Abstract

In the title complex, [Fe(C11H10N5O4)(CH3O)(C5H5N)]·CH4O, the FeIII ion has a distorted penta­gonal-bipyramidal geometry. In the crystal structure, mol­ecules are linked into one-dimensional chains along [1An external file that holds a picture, illustration, etc.
Object name is e-64-00m47-efi1.jpg An external file that holds a picture, illustration, etc.
Object name is e-64-00m47-efi1.jpg] via inter­molecular O—H(...)O and N—H(...)O hydrogen bonds.

Related literature

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

An external file that holds a picture, illustration, etc.
Object name is e-64-00m47-scheme1.jpg

Experimental

Crystal data

  • [Fe(C11H10N5O4)(CH3O)(C5H5N)]·CH4O
  • M r = 475.27
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-00m47-efi3.jpg
  • a = 8.258 (10) Å
  • b = 10.64 (14) Å
  • c = 12.448 (18) Å
  • α = 83.518 (3)°
  • β = 85.924 (3)°
  • γ = 77.176 (2)°
  • V = 1058.4 (2) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.76 mm−1
  • T = 298 (2) K
  • 0.37 × 0.29 × 0.20 mm

Data collection

  • Siemens SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.766, T max = 0.863
  • 5507 measured reflections
  • 3658 independent reflections
  • 2647 reflections with I > 2σ(I)
  • R int = 0.021

Refinement

  • R[F 2 > 2σ(F 2)] = 0.044
  • wR(F 2) = 0.115
  • S = 1.00
  • 3658 reflections
  • 285 parameters
  • H-atom parameters constrained
  • Δρmax = 0.45 e Å−3
  • Δρmin = −0.27 e Å−3

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

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807060862/lh2566sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807060862/lh2566Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors acknowledge the support of the Natural Science Foundation of Shandong Province, People’s Republic of China (Y2003B01).

supplementary crystallographic information

Comment

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 FeIII 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).

Experimental

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%.

Refinement

All H atoms were placed geometrically and treated as riding on their parent atoms, with pyridine C—H distances of 0.93 Å, methyl C—H distances of 0.96 Å, methanol hydroxyl O—H distances of 0.82 Å, hydrazide N—H distances of 0.86Å and Uiso(H)=1.2Ueq(C,N) or 1.5Ueq(O).

Figures

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.

Crystal data

[Fe(C11H10N5O4)(CH3O)(C5H5N)]·CH4OZ = 2
Mr = 475.27F000 = 494
Triclinic, P1Dx = 1.491 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 8.258 (10) ÅCell parameters from 1856 reflections
b = 10.64 (14) Åθ = 2.4–25.1º
c = 12.448 (18) ŵ = 0.76 mm1
α = 83.518 (3)ºT = 298 (2) K
β = 85.924 (3)ºBlock, black
γ = 77.176 (2)º0.37 × 0.29 × 0.20 mm
V = 1058.4 (2) Å3

Data collection

Siemens SMART CCD area-detector diffractometer3658 independent reflections
Radiation source: fine-focus sealed tube2647 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.021
T = 298(2) Kθmax = 25.0º
[var phi] and ω scansθmin = 1.7º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −9→9
Tmin = 0.766, Tmax = 0.863k = −12→9
5507 measured reflectionsl = −14→14

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.115  w = 1/[σ2(Fo2) + (0.050P)2 + 0.8457P] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.004
3658 reflectionsΔρmax = 0.45 e Å3
285 parametersΔρmin = −0.27 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

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)

xyzUiso*/Ueq
Fe10.31969 (6)0.23928 (4)0.23357 (4)0.03344 (18)
N10.2243 (3)0.4328 (2)0.1451 (2)0.0303 (6)
N20.1580 (4)0.3649 (2)0.3383 (2)0.0338 (7)
N30.1451 (4)0.3167 (3)0.4458 (2)0.0384 (7)
H30.09280.36330.49490.046*
N40.4403 (4)0.2535 (3)0.0791 (2)0.0370 (7)
N50.5609 (4)0.1455 (3)0.0544 (2)0.0423 (8)
H50.61170.1395−0.00820.051*
N60.5139 (4)0.3108 (3)0.3122 (2)0.0391 (7)
O10.0049 (3)0.5677 (2)0.37219 (18)0.0445 (7)
O20.4513 (4)0.3481 (2)−0.0965 (2)0.0585 (8)
O30.2966 (3)0.1301 (2)0.39371 (18)0.0441 (7)
O40.5115 (3)0.0678 (2)0.22480 (18)0.0427 (6)
O50.1500 (3)0.1644 (2)0.18472 (19)0.0420 (6)
O60.7483 (4)0.0858 (3)0.8604 (2)0.0673 (9)
H60.77540.00830.85280.101*
C10.0853 (4)0.4869 (3)0.3119 (3)0.0309 (8)
C20.1142 (4)0.5230 (3)0.1937 (3)0.0329 (8)
C30.0382 (5)0.6368 (3)0.1377 (3)0.0466 (10)
H3A−0.03920.69840.17250.056*
C40.0788 (5)0.6583 (4)0.0286 (3)0.0543 (12)
H40.02760.7342−0.01120.065*
C50.1959 (5)0.5662 (3)−0.0208 (3)0.0473 (10)
H5A0.22620.5796−0.09390.057*
C60.2669 (4)0.4542 (3)0.0403 (3)0.0331 (8)
C70.3972 (5)0.3455 (3)−0.0011 (3)0.0374 (9)
C80.2196 (5)0.1930 (3)0.4677 (3)0.0412 (9)
C90.2090 (6)0.1342 (4)0.5816 (3)0.0655 (14)
H9A0.15320.06360.58490.098*
H9B0.14790.19840.62620.098*
H9C0.31900.10260.60720.098*
C100.5907 (5)0.0531 (3)0.1351 (3)0.0394 (9)
C110.7196 (5)−0.0667 (4)0.1174 (3)0.0561 (12)
H11A0.8101−0.07310.16340.084*
H11B0.7600−0.06280.04310.084*
H11C0.6714−0.14130.13410.084*
C120.5929 (5)0.2396 (4)0.3965 (3)0.0560 (11)
H120.58160.15440.41280.067*
C130.6902 (6)0.2880 (6)0.4597 (4)0.0707 (14)
H130.74250.23630.51800.085*
C140.7092 (6)0.4122 (6)0.4364 (4)0.0709 (14)
H140.77230.44720.47920.085*
C150.6335 (6)0.4841 (5)0.3486 (4)0.0683 (13)
H150.64690.56840.32950.082*
C160.5374 (5)0.4305 (4)0.2890 (3)0.0503 (10)
H160.48630.48040.22950.060*
C17−0.0016 (6)0.1640 (4)0.2357 (4)0.0607 (12)
H17A0.01310.11840.30660.091*
H17B−0.06390.12180.19450.091*
H17C−0.06070.25160.24190.091*
C180.7218 (7)0.1580 (4)0.7573 (4)0.0744 (15)
H18A0.67650.24750.76680.112*
H18B0.64540.12480.71950.112*
H18C0.82570.15030.71600.112*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Fe10.0429 (3)0.0265 (3)0.0255 (3)0.0037 (2)0.0005 (2)−0.00328 (19)
N10.0369 (17)0.0263 (14)0.0241 (14)0.0012 (12)−0.0014 (12)−0.0032 (11)
N20.0463 (18)0.0276 (15)0.0221 (14)0.0017 (13)0.0010 (13)−0.0003 (11)
N30.055 (2)0.0319 (16)0.0214 (14)0.0048 (14)0.0045 (13)−0.0049 (12)
N40.0420 (18)0.0321 (16)0.0287 (15)0.0084 (13)0.0021 (13)−0.0035 (13)
N50.052 (2)0.0353 (17)0.0294 (16)0.0109 (14)0.0068 (14)−0.0068 (13)
N60.0381 (18)0.0389 (17)0.0360 (17)0.0006 (14)−0.0005 (14)−0.0041 (14)
O10.0584 (17)0.0358 (14)0.0310 (13)0.0083 (12)0.0053 (12)−0.0092 (11)
O20.082 (2)0.0459 (16)0.0315 (15)0.0122 (14)0.0145 (14)0.0010 (12)
O30.0611 (18)0.0313 (13)0.0317 (14)0.0057 (12)0.0040 (12)−0.0034 (11)
O40.0538 (17)0.0333 (13)0.0307 (14)0.0099 (11)0.0010 (12)−0.0005 (11)
O50.0567 (18)0.0337 (14)0.0334 (14)−0.0041 (12)−0.0006 (12)−0.0066 (11)
O60.099 (3)0.0498 (17)0.0482 (18)−0.0039 (17)0.0139 (16)−0.0173 (14)
C10.0318 (19)0.0311 (18)0.0282 (18)−0.0018 (15)−0.0008 (15)−0.0066 (15)
C20.039 (2)0.0291 (18)0.0282 (18)−0.0007 (15)−0.0013 (15)−0.0071 (14)
C30.062 (3)0.033 (2)0.034 (2)0.0134 (18)0.0006 (18)−0.0034 (16)
C40.074 (3)0.035 (2)0.039 (2)0.014 (2)−0.002 (2)0.0081 (17)
C50.064 (3)0.041 (2)0.0274 (19)0.0053 (19)0.0002 (18)0.0015 (16)
C60.040 (2)0.0290 (18)0.0276 (18)−0.0014 (15)−0.0028 (15)−0.0009 (14)
C70.046 (2)0.0310 (19)0.0296 (19)0.0016 (16)0.0031 (16)−0.0030 (15)
C80.054 (2)0.035 (2)0.0306 (19)−0.0005 (17)−0.0002 (17)−0.0015 (16)
C90.099 (4)0.048 (2)0.034 (2)0.008 (2)0.011 (2)0.0040 (19)
C100.048 (2)0.0324 (19)0.031 (2)0.0069 (16)−0.0005 (17)−0.0080 (16)
C110.067 (3)0.044 (2)0.043 (2)0.020 (2)−0.002 (2)−0.0077 (18)
C120.050 (3)0.060 (3)0.052 (3)−0.003 (2)−0.012 (2)0.008 (2)
C130.055 (3)0.102 (4)0.053 (3)−0.014 (3)−0.020 (2)0.008 (3)
C140.060 (3)0.101 (4)0.062 (3)−0.030 (3)−0.006 (3)−0.020 (3)
C150.061 (3)0.065 (3)0.086 (4)−0.026 (2)−0.011 (3)−0.010 (3)
C160.044 (2)0.051 (3)0.055 (3)−0.0125 (19)−0.003 (2)0.005 (2)
C170.067 (3)0.058 (3)0.058 (3)−0.014 (2)−0.005 (2)−0.006 (2)
C180.109 (4)0.053 (3)0.057 (3)−0.015 (3)0.021 (3)−0.007 (2)

Geometric parameters (Å, °)

Fe1—O51.922 (3)C3—H3A0.9300
Fe1—N42.107 (3)C4—C51.381 (5)
Fe1—O42.142 (2)C4—H40.9300
Fe1—N22.150 (3)C5—C61.375 (5)
Fe1—O32.209 (2)C5—H5A0.9300
Fe1—N12.228 (3)C6—C71.505 (4)
Fe1—N62.245 (3)C8—C91.489 (5)
N1—C21.334 (4)C9—H9A0.9600
N1—C61.334 (4)C9—H9B0.9600
N2—C11.319 (4)C9—H9C0.9600
N2—N31.384 (4)C10—C111.495 (5)
N3—C81.330 (4)C11—H11A0.9600
N3—H30.8600C11—H11B0.9600
N4—C71.325 (4)C11—H11C0.9600
N4—N51.391 (4)C12—C131.377 (6)
N5—C101.320 (4)C12—H120.9300
N5—H50.8600C13—C141.361 (7)
N6—C161.327 (5)C13—H130.9300
N6—C121.341 (4)C14—C151.366 (6)
O1—C11.251 (4)C14—H140.9300
O2—C71.238 (4)C15—C161.374 (6)
O3—C81.252 (4)C15—H150.9300
O4—C101.260 (4)C16—H160.9300
O5—C171.363 (5)C17—H17A0.9600
O6—C181.424 (5)C17—H17B0.9600
O6—H60.8200C17—H17C0.9600
C1—C21.494 (4)C18—H18A0.9600
C2—C31.372 (5)C18—H18B0.9600
C3—C41.381 (5)C18—H18C0.9600
O5—Fe1—N493.67 (11)C6—C5—C4118.6 (3)
O5—Fe1—O494.66 (10)C6—C5—H5A120.7
N4—Fe1—O472.86 (9)C4—C5—H5A120.7
O5—Fe1—N296.21 (11)N1—C6—C5121.5 (3)
N4—Fe1—N2138.16 (10)N1—C6—C7113.4 (3)
O4—Fe1—N2145.91 (10)C5—C6—C7125.1 (3)
O5—Fe1—O388.85 (10)O2—C7—N4128.1 (3)
N4—Fe1—O3149.43 (10)O2—C7—C6122.4 (3)
O4—Fe1—O376.57 (9)N4—C7—C6109.5 (3)
N2—Fe1—O371.46 (9)O3—C8—N3120.0 (3)
O5—Fe1—N193.58 (10)O3—C8—C9122.1 (3)
N4—Fe1—N169.58 (10)N3—C8—C9117.9 (3)
O4—Fe1—N1141.95 (10)C8—C9—H9A109.5
N2—Fe1—N169.30 (10)C8—C9—H9B109.5
O3—Fe1—N1140.72 (9)H9A—C9—H9B109.5
O5—Fe1—N6172.22 (11)C8—C9—H9C109.5
N4—Fe1—N692.96 (11)H9A—C9—H9C109.5
O4—Fe1—N683.42 (10)H9B—C9—H9C109.5
N2—Fe1—N681.48 (11)O4—C10—N5119.8 (3)
O3—Fe1—N683.37 (10)O4—C10—C11121.7 (3)
N1—Fe1—N692.54 (10)N5—C10—C11118.6 (3)
C2—N1—C6120.0 (3)C10—C11—H11A109.5
C2—N1—Fe1120.3 (2)C10—C11—H11B109.5
C6—N1—Fe1119.5 (2)H11A—C11—H11B109.5
C1—N2—N3117.5 (3)C10—C11—H11C109.5
C1—N2—Fe1125.9 (2)H11A—C11—H11C109.5
N3—N2—Fe1116.18 (18)H11B—C11—H11C109.5
C8—N3—N2114.9 (3)N6—C12—C13122.4 (4)
C8—N3—H3122.5N6—C12—H12118.8
N2—N3—H3122.5C13—C12—H12118.8
C7—N4—N5116.8 (3)C14—C13—C12119.6 (4)
C7—N4—Fe1126.6 (2)C14—C13—H13120.2
N5—N4—Fe1115.8 (2)C12—C13—H13120.2
C10—N5—N4114.3 (3)C13—C14—C15118.5 (4)
C10—N5—H5122.9C13—C14—H14120.8
N4—N5—H5122.9C15—C14—H14120.8
C16—N6—C12117.2 (4)C14—C15—C16119.2 (5)
C16—N6—Fe1122.0 (3)C14—C15—H15120.4
C12—N6—Fe1120.1 (3)C16—C15—H15120.4
C8—O3—Fe1116.7 (2)N6—C16—C15123.2 (4)
C10—O4—Fe1117.0 (2)N6—C16—H16118.4
C17—O5—Fe1125.7 (2)C15—C16—H16118.4
C18—O6—H6109.5O5—C17—H17A109.5
O1—C1—N2128.4 (3)O5—C17—H17B109.5
O1—C1—C2121.3 (3)H17A—C17—H17B109.5
N2—C1—C2110.3 (3)O5—C17—H17C109.5
N1—C2—C3121.6 (3)H17A—C17—H17C109.5
N1—C2—C1113.5 (3)H17B—C17—H17C109.5
C3—C2—C1125.0 (3)O6—C18—H18A109.5
C2—C3—C4118.8 (3)O6—C18—H18B109.5
C2—C3—H3A120.6H18A—C18—H18B109.5
C4—C3—H3A120.6O6—C18—H18C109.5
C3—C4—C5119.5 (3)H18A—C18—H18C109.5
C3—C4—H4120.3H18B—C18—H18C109.5
C5—C4—H4120.3
O5—Fe1—N1—C291.5 (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—C10175.0 (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—C17127.8 (3)
N4—Fe1—N1—C69.8 (2)N2—Fe1—O5—C17−19.8 (3)
O4—Fe1—N1—C619.5 (3)O3—Fe1—O5—C1751.4 (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—O10.5 (6)
N6—Fe1—N1—C6102.0 (3)Fe1—N2—C1—O1−171.7 (3)
O5—Fe1—N2—C1−93.7 (3)N3—N2—C1—C2179.0 (3)
N4—Fe1—N2—C18.9 (4)Fe1—N2—C1—C26.8 (4)
O4—Fe1—N2—C1158.5 (2)C6—N1—C2—C32.2 (5)
O3—Fe1—N2—C1179.6 (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—C193.8 (3)Fe1—N1—C2—C18.3 (4)
O5—Fe1—N2—N394.0 (2)O1—C1—C2—N1169.5 (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—N37.3 (2)N2—C1—C2—C3171.1 (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—C4179.0 (4)
C1—N2—N3—C8179.5 (3)C2—C3—C4—C5−1.0 (6)
Fe1—N2—N3—C8−7.5 (4)C3—C4—C5—C61.1 (7)
O5—Fe1—N4—C781.0 (3)C2—N1—C6—C5−2.1 (5)
O4—Fe1—N4—C7174.7 (3)Fe1—N1—C6—C5172.1 (3)
N2—Fe1—N4—C7−22.6 (4)C2—N1—C6—C7177.7 (3)
O3—Fe1—N4—C7174.9 (3)Fe1—N1—C6—C7−8.0 (4)
N1—Fe1—N4—C7−11.5 (3)C4—C5—C6—N10.4 (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—N55.1 (2)Fe1—N4—C7—O2−169.8 (3)
N2—Fe1—N4—N5167.8 (2)N5—N4—C7—C6−179.7 (3)
O3—Fe1—N4—N55.3 (4)Fe1—N4—C7—C610.7 (4)
N1—Fe1—N4—N5178.9 (3)N1—C6—C7—O2179.6 (4)
N6—Fe1—N4—N587.3 (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—N4179.0 (4)
N4—Fe1—N6—C1665.6 (3)Fe1—O3—C8—N35.4 (5)
O4—Fe1—N6—C16138.0 (3)Fe1—O3—C8—C9−174.0 (3)
N2—Fe1—N6—C16−72.7 (3)N2—N3—C8—O31.3 (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—N54.4 (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—O40.2 (5)
N2—Fe1—N6—C1297.1 (3)N4—N5—C10—C11−179.4 (3)
O3—Fe1—N6—C1224.9 (3)C16—N6—C12—C132.2 (6)
N1—Fe1—N6—C12165.7 (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—C8161.0 (3)C12—C13—C14—C15−1.5 (7)
O4—Fe1—O3—C8161.2 (3)C13—C14—C15—C161.8 (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—C15168.1 (3)
N6—Fe1—O3—C876.4 (3)C14—C15—C16—N6−0.1 (7)
O5—Fe1—O4—C1087.3 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N3—H3···O1i0.861.942.780 (3)167
N5—H5···O6ii0.861.982.830 (4)167
O6—H6···O5iii0.821.902.718 (3)172

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2566).

References

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