Literature DB >> 21581516

Chlorido{N,N'-o-phenyl-ene-[6,6'-ethyl-enebis(pyridine-2-carboxamide)]}iron(III).

Li Yang, Bin Tang.   

Abstract

In the title compound, [Fe(C(20)n class="Species">H(14)N(4)O(2))Cl], the Fe(III) ion is in a distorted square-pyramidal environment, with two pyridine and two deprotonated amide N atoms in the basal plane and the Cl ion in the apical position. The Fe(III) ion is displaced from the basal plane of the square- pyramid towards the apical Cl atom by 0.2942 (4) Å. The mol-ecules are linked into a three-dimensional network by C-H⋯Cl and C-H⋯O hydrogen bonds.

Entities:  

Year:  2008        PMID： 21581516      PMCID： PMC2967889          DOI： 10.1107/S1600536808041354

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For general background, see: Liu et al. (2006 ▶); Yang et al. (2007 ▶); Momenteau & Reed (1994 ▶). For related structures, see: Rath et al. (2004 ▶); Xu et al. (2007 ▶).

Experimental

Crystal data

[Fe(C20n class="Species">H14N4O2)Cl] M = 433.65 Monoclinic, a = 11.8532 (2) Å b = 8.2028 (1) Å c = 19.3507 (3) Å β = 106.889 (1)° V = 1800.31 (5) Å3 Z = 4 Mo Kα radiation μ = 1.01 mm−1 T = 296 (2) K 0.44 × 0.16 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer Absorption correction: multi-scan (SADABS, Sheldrick, 1996 ▶) T min = 0.778, T max = 1.000 (expected range = 0.703–0.904) 24687 measured reflections 4142 independent reflections 3415 reflections with I > 2σ(I) R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.040 wR(F 2) = 0.126 S = 1.01 4142 reflections 253 parameters H-atom parameters constrained Δρmax = 0.62 e Å−3 Δρmin = −0.43 e Å−3 Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; 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. Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808041354/ci2736sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808041354/ci2736Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Fe(C20H14N4O2)Cl]F(000) = 884
Mr = 433.65Dx = 1.600 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 9989 reflections
a = 11.8532 (2) Åθ = 2.2–27.4°
b = 8.2028 (1) ŵ = 1.01 mm−1
c = 19.3507 (3) ÅT = 296 K
β = 106.889 (1)°Plate, black
V = 1800.31 (5) Å30.44 × 0.16 × 0.10 mm
Z = 4
Bruker SMART CCD area-detector diffractometer4142 independent reflections
Radiation source: fine-focus sealed tube3415 reflections with I > 2σ(I)
graphiteRint = 0.041
φ and ω scansθmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS, Sheldrick, 1996)h = −15→15
Tmin = 0.778, Tmax = 1.000k = −10→10
24687 measured reflectionsl = −25→25
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126H-atom parameters constrained
S = 1.00w = 1/[σ2(Fo2) + (0.0642P)2 + 2.4383P] where P = (Fo2 + 2Fc2)/3
4142 reflections(Δ/σ)max = 0.001
253 parametersΔρmax = 0.62 e Å−3
0 restraintsΔρmin = −0.43 e Å−3
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 F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > σ(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.
xyzUiso*/Ueq
Fe10.45008 (3)0.56516 (5)0.62759 (2)0.02844 (13)
Cl10.49959 (7)0.48979 (10)0.74759 (4)0.0423 (2)
O10.1136 (2)0.6292 (4)0.61432 (18)0.0676 (8)
O20.5587 (2)0.2335 (3)0.51016 (14)0.0529 (6)
N10.2870 (2)0.5301 (3)0.59827 (14)0.0352 (5)
N20.4003 (2)0.7937 (3)0.64688 (12)0.0321 (5)
N30.6194 (2)0.5763 (3)0.62630 (12)0.0298 (5)
N40.44925 (19)0.3762 (3)0.57162 (12)0.0305 (5)
C10.2181 (3)0.6411 (4)0.61888 (17)0.0399 (7)
C20.2867 (3)0.7921 (4)0.64770 (16)0.0373 (6)
C30.2337 (3)0.9212 (4)0.67153 (19)0.0509 (9)
H3A0.15550.91560.67190.061*
C40.3014 (4)1.0606 (5)0.6950 (2)0.0564 (10)
H4A0.26961.14950.71270.068*
C50.4145 (4)1.0649 (4)0.69173 (18)0.0483 (8)
H5A0.45941.15850.70620.058*
C60.4643 (3)0.9306 (4)0.66690 (16)0.0377 (7)
C70.5853 (3)0.9393 (4)0.65875 (18)0.0443 (7)
H7A0.61591.04830.67160.053*
H7B0.58000.92220.60830.053*
C80.6751 (3)0.8146 (4)0.70492 (17)0.0418 (7)
H8A0.74680.87220.73010.050*
H8B0.64250.76830.74110.050*
C90.7061 (2)0.6787 (4)0.66208 (15)0.0352 (6)
C100.8207 (3)0.6559 (4)0.65877 (18)0.0453 (8)
H10A0.87940.72870.68240.054*
C110.8485 (3)0.5277 (5)0.62112 (19)0.0479 (8)
H11A0.92550.51240.61950.057*
C120.7599 (3)0.4217 (4)0.58564 (17)0.0413 (7)
H12A0.77600.33310.56000.050*
C130.6471 (2)0.4504 (3)0.58911 (15)0.0314 (6)
C140.5471 (2)0.3397 (4)0.55255 (15)0.0333 (6)
C150.2484 (2)0.3809 (4)0.56301 (16)0.0348 (6)
C160.1338 (3)0.3196 (4)0.5414 (2)0.0499 (8)
H16A0.07240.37730.55090.060*
C170.1128 (3)0.1721 (5)0.5056 (2)0.0590 (10)
H17A0.03640.13110.49050.071*
C180.2030 (3)0.0846 (4)0.4919 (2)0.0547 (9)
H18A0.1870−0.01530.46830.066*
C190.3178 (3)0.1438 (4)0.51280 (16)0.0414 (7)
H19A0.37890.08400.50410.050*
C200.3393 (2)0.2947 (3)0.54712 (15)0.0328 (6)
U11U22U33U12U13U23
Fe10.0262 (2)0.0225 (2)0.0375 (2)−0.00026 (14)0.01073 (15)−0.00375 (15)
Cl10.0483 (4)0.0381 (4)0.0427 (4)0.0044 (3)0.0169 (3)0.0083 (3)
O10.0352 (13)0.0650 (18)0.109 (2)0.0042 (12)0.0307 (14)−0.0117 (17)
O20.0472 (13)0.0475 (14)0.0671 (15)0.0005 (11)0.0215 (11)−0.0268 (12)
N10.0278 (11)0.0299 (13)0.0484 (14)0.0000 (9)0.0119 (10)−0.0014 (10)
N20.0410 (13)0.0221 (11)0.0345 (12)0.0034 (10)0.0132 (10)−0.0013 (9)
N30.0287 (11)0.0274 (12)0.0334 (11)−0.0026 (9)0.0091 (9)−0.0020 (9)
N40.0301 (11)0.0237 (11)0.0370 (12)−0.0025 (9)0.0088 (9)−0.0049 (9)
C10.0337 (15)0.0377 (17)0.0515 (17)0.0065 (12)0.0175 (13)0.0020 (14)
C20.0424 (16)0.0333 (15)0.0396 (15)0.0099 (12)0.0173 (12)0.0021 (12)
C30.058 (2)0.047 (2)0.055 (2)0.0213 (17)0.0282 (17)0.0042 (16)
C40.083 (3)0.0406 (19)0.0494 (19)0.0225 (19)0.0254 (18)−0.0016 (15)
C50.076 (2)0.0272 (15)0.0401 (16)0.0053 (15)0.0136 (16)−0.0027 (13)
C60.0547 (18)0.0249 (14)0.0325 (14)0.0017 (13)0.0108 (12)0.0010 (11)
C70.0553 (19)0.0264 (15)0.0517 (18)−0.0103 (13)0.0166 (15)−0.0024 (13)
C80.0421 (16)0.0388 (17)0.0411 (16)−0.0095 (13)0.0069 (13)−0.0082 (13)
C90.0322 (14)0.0346 (15)0.0365 (14)−0.0063 (12)0.0066 (11)−0.0002 (12)
C100.0314 (15)0.051 (2)0.0500 (18)−0.0110 (14)0.0058 (13)0.0020 (15)
C110.0270 (14)0.063 (2)0.0540 (19)0.0007 (14)0.0126 (13)0.0059 (17)
C120.0330 (15)0.0472 (19)0.0462 (17)0.0054 (13)0.0154 (13)0.0001 (14)
C130.0311 (13)0.0311 (14)0.0321 (13)0.0019 (11)0.0092 (10)0.0020 (11)
C140.0339 (14)0.0296 (14)0.0360 (14)0.0024 (11)0.0094 (11)−0.0030 (11)
C150.0318 (14)0.0287 (14)0.0423 (15)−0.0045 (11)0.0084 (11)0.0036 (12)
C160.0325 (16)0.0450 (19)0.070 (2)−0.0058 (14)0.0115 (15)0.0041 (17)
C170.0431 (19)0.047 (2)0.079 (3)−0.0221 (16)0.0051 (17)0.0039 (19)
C180.063 (2)0.0346 (18)0.059 (2)−0.0211 (16)0.0073 (17)−0.0051 (15)
C190.0493 (18)0.0317 (16)0.0420 (16)−0.0082 (13)0.0114 (13)−0.0036 (13)
C200.0326 (14)0.0281 (14)0.0360 (14)−0.0047 (11)0.0073 (11)0.0012 (11)
Fe1—N11.871 (2)C7—C81.557 (5)
Fe1—N41.889 (2)C7—H7A0.97
Fe1—N32.016 (2)C7—H7B0.97
Fe1—N22.032 (2)C8—C91.497 (4)
Fe1—Cl12.3080 (8)C8—H8A0.97
O1—C11.220 (4)C8—H8B0.97
O2—C141.231 (3)C9—C101.392 (4)
N1—C11.358 (4)C10—C111.373 (5)
N1—C151.412 (4)C10—H10A0.93
N2—C61.348 (4)C11—C121.383 (5)
N2—C21.350 (4)C11—H11A0.93
N3—C91.352 (4)C12—C131.378 (4)
N3—C131.353 (4)C12—H12A0.93
N4—C141.349 (4)C13—C141.498 (4)
N4—C201.418 (3)C15—C161.394 (4)
C1—C21.498 (5)C15—C201.396 (4)
C2—C31.378 (4)C16—C171.380 (5)
C3—C41.395 (6)C16—H16A0.93
C3—H3A0.93C17—C181.376 (6)
C4—C51.361 (6)C17—H17A0.93
C4—H4A0.93C18—C191.390 (5)
C5—C61.399 (4)C18—H18A0.93
C5—H5A0.93C19—C201.392 (4)
C6—C71.490 (5)C19—H19A0.93
N1—Fe1—N482.38 (10)C8—C7—H7B108.5
N1—Fe1—N3161.28 (10)H7A—C7—H7B107.5
N4—Fe1—N382.51 (9)C9—C8—C7114.1 (3)
N1—Fe1—N282.39 (10)C9—C8—H8A108.7
N4—Fe1—N2155.32 (10)C7—C8—H8A108.7
N3—Fe1—N2107.69 (10)C9—C8—H8B108.7
N1—Fe1—Cl1101.67 (8)C7—C8—H8B108.7
N4—Fe1—Cl1108.32 (8)H8A—C8—H8B107.6
N3—Fe1—Cl193.53 (7)N3—C9—C10120.1 (3)
N2—Fe1—Cl193.71 (7)N3—C9—C8118.3 (3)
C1—N1—C15125.8 (3)C10—C9—C8121.7 (3)
C1—N1—Fe1117.7 (2)C11—C10—C9121.0 (3)
C15—N1—Fe1116.19 (19)C11—C10—H10A119.5
C6—N2—C2119.0 (3)C9—C10—H10A119.5
C6—N2—Fe1130.7 (2)C10—C11—C12118.7 (3)
C2—N2—Fe1109.69 (19)C10—C11—H11A120.6
C9—N3—C13118.7 (2)C12—C11—H11A120.6
C9—N3—Fe1129.3 (2)C13—C12—C11118.4 (3)
C13—N3—Fe1111.65 (18)C13—C12—H12A120.8
C14—N4—C20125.7 (2)C11—C12—H12A120.8
C14—N4—Fe1118.49 (18)N3—C13—C12123.1 (3)
C20—N4—Fe1115.45 (18)N3—C13—C14115.6 (2)
O1—C1—N1127.6 (3)C12—C13—C14121.3 (3)
O1—C1—C2121.5 (3)O2—C14—N4127.6 (3)
N1—C1—C2110.8 (2)O2—C14—C13121.2 (3)
N2—C2—C3123.4 (3)N4—C14—C13111.2 (2)
N2—C2—C1116.0 (2)C16—C15—C20119.9 (3)
C3—C2—C1120.6 (3)C16—C15—N1127.5 (3)
C2—C3—C4117.6 (3)C20—C15—N1112.5 (2)
C2—C3—H3A121.2C17—C16—C15119.0 (3)
C4—C3—H3A121.2C17—C16—H16A120.5
C5—C4—C3119.1 (3)C15—C16—H16A120.5
C5—C4—H4A120.4C18—C17—C16121.1 (3)
C3—C4—H4A120.4C18—C17—H17A119.4
C4—C5—C6121.0 (3)C16—C17—H17A119.4
C4—C5—H5A119.5C17—C18—C19120.8 (3)
C6—C5—H5A119.5C17—C18—H18A119.6
N2—C6—C5119.8 (3)C19—C18—H18A119.6
N2—C6—C7119.2 (3)C18—C19—C20118.5 (3)
C5—C6—C7120.9 (3)C18—C19—H19A120.7
C6—C7—C8115.3 (3)C20—C19—H19A120.7
C6—C7—H7A108.5C19—C20—C15120.6 (3)
C8—C7—H7A108.5C19—C20—N4127.0 (3)
C6—C7—H7B108.5C15—C20—N4112.4 (2)
N4—Fe1—N1—C1−176.9 (2)C2—N2—C6—C7−173.6 (3)
N3—Fe1—N1—C1−140.5 (3)Fe1—N2—C6—C716.6 (4)
N2—Fe1—N1—C1−16.3 (2)C4—C5—C6—N2−1.0 (5)
Cl1—Fe1—N1—C175.9 (2)C4—C5—C6—C7175.9 (3)
N4—Fe1—N1—C159.6 (2)N2—C6—C7—C8−63.1 (4)
N3—Fe1—N1—C1546.0 (4)C5—C6—C7—C8119.9 (3)
N2—Fe1—N1—C15170.1 (2)C6—C7—C8—C9107.4 (3)
Cl1—Fe1—N1—C15−97.6 (2)C13—N3—C9—C101.6 (4)
N1—Fe1—N2—C6−173.7 (3)Fe1—N3—C9—C10174.0 (2)
N4—Fe1—N2—C6−121.4 (3)C13—N3—C9—C8−178.2 (3)
N3—Fe1—N2—C6−9.9 (3)Fe1—N3—C9—C8−5.7 (4)
Cl1—Fe1—N2—C685.0 (2)C7—C8—C9—N3−62.5 (4)
N1—Fe1—N2—C215.76 (19)C7—C8—C9—C10117.7 (3)
N4—Fe1—N2—C268.1 (3)N3—C9—C10—C11−1.8 (5)
N3—Fe1—N2—C2179.57 (18)C8—C9—C10—C11177.9 (3)
Cl1—Fe1—N2—C2−85.53 (19)C9—C10—C11—C120.7 (5)
N1—Fe1—N3—C9150.2 (3)C10—C11—C12—C130.6 (5)
N4—Fe1—N3—C9−173.5 (3)C9—N3—C13—C12−0.3 (4)
N2—Fe1—N3—C929.6 (3)Fe1—N3—C13—C12−174.0 (2)
Cl1—Fe1—N3—C9−65.4 (2)C9—N3—C13—C14178.4 (2)
N1—Fe1—N3—C13−37.0 (4)Fe1—N3—C13—C144.7 (3)
N4—Fe1—N3—C13−0.60 (19)C11—C12—C13—N3−0.8 (5)
N2—Fe1—N3—C13−157.53 (18)C11—C12—C13—C14−179.4 (3)
Cl1—Fe1—N3—C13107.44 (18)C20—N4—C14—O21.6 (5)
N1—Fe1—N4—C14164.8 (2)Fe1—N4—C14—O2−171.3 (3)
N3—Fe1—N4—C14−4.1 (2)C20—N4—C14—C13−179.7 (2)
N2—Fe1—N4—C14112.5 (3)Fe1—N4—C14—C137.5 (3)
Cl1—Fe1—N4—C14−95.4 (2)N3—C13—C14—O2171.0 (3)
N1—Fe1—N4—C20−8.8 (2)C12—C13—C14—O2−10.3 (4)
N3—Fe1—N4—C20−177.7 (2)N3—C13—C14—N4−7.8 (4)
N2—Fe1—N4—C20−61.1 (3)C12—C13—C14—N4170.9 (3)
Cl1—Fe1—N4—C2091.03 (19)C1—N1—C15—C161.3 (5)
C15—N1—C1—O14.1 (6)Fe1—N1—C15—C16174.3 (3)
Fe1—N1—C1—O1−168.8 (3)C1—N1—C15—C20178.5 (3)
C15—N1—C1—C2−174.1 (3)Fe1—N1—C15—C20−8.6 (3)
Fe1—N1—C1—C213.1 (3)C20—C15—C16—C171.3 (5)
C6—N2—C2—C3−3.4 (4)N1—C15—C16—C17178.3 (3)
Fe1—N2—C2—C3168.4 (3)C15—C16—C17—C180.7 (6)
C6—N2—C2—C1175.0 (3)C16—C17—C18—C19−1.0 (6)
Fe1—N2—C2—C1−13.2 (3)C17—C18—C19—C20−0.8 (5)
O1—C1—C2—N2−176.9 (3)C18—C19—C20—C152.8 (5)
N1—C1—C2—N21.3 (4)C18—C19—C20—N4−179.2 (3)
O1—C1—C2—C31.5 (5)C16—C15—C20—C19−3.1 (5)
N1—C1—C2—C3179.8 (3)N1—C15—C20—C19179.5 (3)
N2—C2—C3—C40.8 (5)C16—C15—C20—N4178.7 (3)
C1—C2—C3—C4−177.5 (3)N1—C15—C20—N41.3 (4)
C2—C3—C4—C51.6 (5)C14—N4—C20—C1915.3 (5)
C3—C4—C5—C6−1.5 (5)Fe1—N4—C20—C19−171.7 (2)
C2—N2—C6—C53.4 (4)C14—N4—C20—C15−166.7 (3)
Fe1—N2—C6—C5−166.4 (2)Fe1—N4—C20—C156.4 (3)
D—H···AD—HH···AD···AD—H···A
C3—H3A···Cl1i0.932.803.595 (4)144
C10—H10A···Cl1ii0.932.713.617 (3)165
C11—H11A···O1iii0.932.463.290 (5)149
Table 1

Selected bond lengths (Å)

Fe1—N11.871 (2)
Fe1—N41.889 (2)
Fe1—N32.016 (2)
Fe1—N22.032 (2)
Fe1—Cl12.3080 (8)
Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C3—H3A⋯Cl1i0.932.803.595 (4)144
C10—H10A⋯Cl1ii0.932.713.617 (3)165
C11—H11A⋯O1iii0.932.463.290 (5)149

Symmetry codes: (i) ; (ii) ; (iii) .

  2 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  Facile ring opening of iron(III) and iron(II) complexes of meso-amino-octaethylporphyrin by dioxygen.

Authors:  Sankar Prasad Rath; Heather Kalish; Lechosław Latos-Grazyński; Marilyn M Olmstead; Alan L Balch
Journal:  J Am Chem Soc       Date:  2004-01-21       Impact factor: 15.419
  2 in total

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