metal-organic compounds
Tris[2-(benzyliminomethyl)phenolato-κ2N,O]iron(III)
aXuzhou Central Hospital, Xuzhou 221009, People's Republic of China
*Correspondence e-mail: adler_20008@yahoo.com.cn
In the title compound, [Fe(C14H12NO)3], the FeIII atom has a slightly distorted octahedral geometry and is coordinated by three Schiff base ligands, viz. 2-(benzyliminomethyl)phenolate. The is stabilized by intramolecular C—H⋯O and C—H⋯N hydrogen bonds.
Related literature
For related literature, see: Liu et al. (2004); You & Zhu (2004); You et al. (2004, 2005); Zhu, Xia et al. (2003); Zhu, Zeng et al. (2003).
Experimental
Crystal data
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Refinement
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Data collection: SMART (Siemens, 1996); cell SAINT (Siemens, 1996); 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
Supporting information
10.1107/S1600536808001566/bx2126sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808001566/bx2126Isup2.hkl
Benzylamine and salicylaldehyde were available commercially and were used without further purification. Benzylamine (0.3 mmol, 32.0 mg) and salicylaldehyde (0.3 mmol, 36.7 mg) were dissolved in acetonitrile solution (20 ml). The mixture was stirred for 1 h to obtain a clear red solution of HL (0.3 mmol), where HL is 2-(benzyliminomethyl)phenol.To the solution of HL was added a solution of
Fe(ClO4)2×6×H2O (0.1 mmol, 38.9 mg) in acetonitrile (10 ml), with stirring. After keeping the resulting solution in air for 2 days, yielding large purple crystals. The crystals were isolated, washed three times with acetonitrile and methanol (yield 79%).
C-bound H atoms were included in the riding model approximation with C—H = 0.93–0.97 Å, and with Uiso(H) = 1.2Ueq(C).
Data collection: SMART (Siemens, 1996); cell
SMART (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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 (Sheldrick, 2008).[Fe(C14H12NO)3] | Z = 2 |
Mr = 686.59 | F(000) = 718 |
Triclinic, P1 | Dx = 1.350 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.3470 (8) Å | Cell parameters from 2702 reflections |
b = 10.9248 (13) Å | θ = 2.7–27.9° |
c = 16.7702 (19) Å | µ = 0.49 mm−1 |
α = 95.42 (3)° | T = 293 K |
β = 96.47 (3)° | Prism, purple |
γ = 93.88 (3)° | 0.40 × 0.30 × 0.20 mm |
V = 1688.6 (3) Å3 |
Bruker APEX area-detector diffractometer | 6624 independent reflections |
Radiation source: fine-focus sealed tube | 4330 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
ϕ and ω scans | θmax = 26.0°, θmin = 1.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = 0→11 |
Tmin = 0.828, Tmax = 0.908 | k = −13→13 |
7053 measured reflections | l = −20→20 |
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)] = 0.057 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.152 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0661P)2 + 0.6392P] where P = (Fo2 + 2Fc2)/3 |
6624 reflections | (Δ/σ)max < 0.001 |
442 parameters | Δρmax = 0.59 e Å−3 |
0 restraints | Δρmin = −0.52 e Å−3 |
[Fe(C14H12NO)3] | γ = 93.88 (3)° |
Mr = 686.59 | V = 1688.6 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.3470 (8) Å | Mo Kα radiation |
b = 10.9248 (13) Å | µ = 0.49 mm−1 |
c = 16.7702 (19) Å | T = 293 K |
α = 95.42 (3)° | 0.40 × 0.30 × 0.20 mm |
β = 96.47 (3)° |
Bruker APEX area-detector diffractometer | 6624 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 4330 reflections with I > 2σ(I) |
Tmin = 0.828, Tmax = 0.908 | Rint = 0.035 |
7053 measured reflections |
R[F2 > 2σ(F2)] = 0.057 | 0 restraints |
wR(F2) = 0.152 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.59 e Å−3 |
6624 reflections | Δρmin = −0.52 e Å−3 |
442 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Fe | 0.82215 (5) | 0.23502 (4) | 0.78274 (3) | 0.03716 (16) | |
O1 | 1.0232 (3) | 0.2737 (2) | 0.78948 (16) | 0.0554 (7) | |
O2 | 0.7939 (3) | 0.4060 (2) | 0.79542 (15) | 0.0497 (6) | |
O3 | 0.6202 (3) | 0.2022 (2) | 0.76423 (15) | 0.0458 (6) | |
N1 | 0.8205 (3) | 0.2453 (2) | 0.89852 (18) | 0.0440 (7) | |
N2 | 0.8234 (3) | 0.2396 (3) | 0.66785 (18) | 0.0461 (7) | |
N3 | 0.8477 (3) | 0.0590 (3) | 0.77627 (18) | 0.0449 (7) | |
C1 | 1.0614 (4) | 0.3518 (3) | 0.9288 (3) | 0.0515 (10) | |
C2 | 1.1043 (4) | 0.3354 (3) | 0.8506 (3) | 0.0511 (10) | |
C3 | 1.2425 (5) | 0.3852 (4) | 0.8396 (3) | 0.0690 (13) | |
H3 | 1.2742 | 0.3734 | 0.7891 | 0.083* | |
C4 | 1.3309 (5) | 0.4502 (4) | 0.9013 (4) | 0.0800 (15) | |
H4 | 1.4216 | 0.4821 | 0.8921 | 0.096* | |
C5 | 1.2884 (5) | 0.4696 (4) | 0.9774 (4) | 0.0767 (15) | |
H5 | 1.3490 | 0.5158 | 1.0188 | 0.092* | |
C6 | 1.1556 (5) | 0.4201 (4) | 0.9913 (3) | 0.0646 (12) | |
H6 | 1.1274 | 0.4318 | 1.0427 | 0.077* | |
C7 | 0.9239 (4) | 0.3019 (3) | 0.9480 (2) | 0.0492 (9) | |
H7 | 0.9087 | 0.3118 | 1.0020 | 0.059* | |
C8 | 0.6871 (4) | 0.2082 (3) | 0.9334 (2) | 0.0498 (9) | |
H8A | 0.6051 | 0.2382 | 0.9025 | 0.060* | |
H8B | 0.6934 | 0.2474 | 0.9882 | 0.060* | |
C9 | 0.6603 (4) | 0.0696 (3) | 0.9346 (2) | 0.0491 (9) | |
C10 | 0.5434 (5) | 0.0044 (4) | 0.8898 (3) | 0.0606 (11) | |
H10 | 0.4807 | 0.0448 | 0.8560 | 0.073* | |
C11 | 0.5173 (6) | −0.1225 (4) | 0.8942 (3) | 0.0735 (13) | |
H11 | 0.4382 | −0.1663 | 0.8633 | 0.088* | |
C12 | 0.6085 (6) | −0.1811 (4) | 0.9442 (3) | 0.0737 (14) | |
H12 | 0.5919 | −0.2654 | 0.9470 | 0.088* | |
C13 | 0.7231 (6) | −0.1176 (4) | 0.9900 (3) | 0.0779 (15) | |
H13 | 0.7840 | −0.1581 | 1.0246 | 0.093* | |
C14 | 0.7501 (5) | 0.0081 (4) | 0.9854 (3) | 0.0657 (12) | |
H14 | 0.8292 | 0.0512 | 1.0169 | 0.079* | |
C15 | 0.6688 (4) | 0.4070 (3) | 0.6628 (2) | 0.0469 (9) | |
C16 | 0.7035 (4) | 0.4535 (3) | 0.7443 (2) | 0.0462 (9) | |
C17 | 0.6398 (4) | 0.5617 (3) | 0.7711 (3) | 0.0554 (10) | |
H17 | 0.6631 | 0.5964 | 0.8242 | 0.066* | |
C18 | 0.5452 (5) | 0.6154 (4) | 0.7204 (3) | 0.0678 (12) | |
H18 | 0.5058 | 0.6869 | 0.7394 | 0.081* | |
C19 | 0.5059 (5) | 0.5666 (4) | 0.6413 (3) | 0.0706 (13) | |
H19 | 0.4377 | 0.6023 | 0.6080 | 0.085* | |
C20 | 0.5700 (5) | 0.4642 (4) | 0.6128 (3) | 0.0627 (11) | |
H20 | 0.5470 | 0.4325 | 0.5591 | 0.075* | |
C21 | 0.7481 (4) | 0.3114 (3) | 0.6284 (2) | 0.0519 (10) | |
H21 | 0.7441 | 0.3011 | 0.5725 | 0.062* | |
C22 | 0.9185 (5) | 0.1603 (4) | 0.6228 (3) | 0.0639 (12) | |
H22A | 0.8593 | 0.0906 | 0.5933 | 0.077* | |
H22B | 0.9875 | 0.1282 | 0.6616 | 0.077* | |
C23 | 1.0000 (4) | 0.2252 (4) | 0.5645 (3) | 0.0560 (10) | |
C24 | 1.0837 (6) | 0.3340 (5) | 0.5903 (4) | 0.1012 (19) | |
H24 | 1.0897 | 0.3679 | 0.6437 | 0.121* | |
C25 | 1.1584 (8) | 0.3918 (7) | 0.5359 (6) | 0.142 (3) | |
H25 | 1.2131 | 0.4659 | 0.5527 | 0.171* | |
C26 | 1.1532 (8) | 0.3413 (8) | 0.4574 (5) | 0.126 (3) | |
H26 | 1.2052 | 0.3801 | 0.4215 | 0.151* | |
C27 | 1.0715 (7) | 0.2346 (7) | 0.4328 (3) | 0.1002 (19) | |
H27 | 1.0670 | 0.1998 | 0.3797 | 0.120* | |
C28 | 0.9951 (5) | 0.1775 (4) | 0.4861 (3) | 0.0682 (12) | |
H28 | 0.9387 | 0.1045 | 0.4683 | 0.082* | |
C29 | 0.6256 (4) | 0.0056 (3) | 0.6874 (2) | 0.0460 (9) | |
C30 | 0.5625 (4) | 0.1171 (3) | 0.7069 (2) | 0.0452 (9) | |
C31 | 0.4290 (4) | 0.1352 (4) | 0.6627 (3) | 0.0578 (11) | |
H31 | 0.3837 | 0.2067 | 0.6745 | 0.069* | |
C32 | 0.3658 (5) | 0.0481 (4) | 0.6025 (3) | 0.0719 (13) | |
H32 | 0.2786 | 0.0624 | 0.5737 | 0.086* | |
C33 | 0.4289 (5) | −0.0614 (4) | 0.5834 (3) | 0.0701 (13) | |
H33 | 0.3855 | −0.1192 | 0.5420 | 0.084* | |
C34 | 0.5557 (5) | −0.0814 (4) | 0.6269 (3) | 0.0607 (11) | |
H34 | 0.5969 | −0.1553 | 0.6159 | 0.073* | |
C35 | 0.7575 (4) | −0.0208 (3) | 0.7334 (2) | 0.0494 (9) | |
H35 | 0.7788 | −0.1029 | 0.7317 | 0.059* | |
C36 | 0.9731 (5) | 0.0181 (4) | 0.8270 (3) | 0.0612 (11) | |
H36A | 0.9460 | 0.0117 | 0.8806 | 0.073* | |
H36B | 1.0515 | 0.0823 | 0.8317 | 0.073* | |
C37 | 1.0300 (4) | −0.1014 (3) | 0.7987 (2) | 0.0467 (9) | |
C38 | 0.9776 (5) | −0.2134 (4) | 0.8207 (3) | 0.0614 (11) | |
H38 | 0.9019 | −0.2159 | 0.8522 | 0.074* | |
C39 | 1.0363 (6) | −0.3212 (4) | 0.7965 (3) | 0.0774 (14) | |
H39 | 1.0000 | −0.3959 | 0.8115 | 0.093* | |
C40 | 1.1473 (6) | −0.3183 (5) | 0.7507 (3) | 0.0885 (17) | |
H40 | 1.1868 | −0.3910 | 0.7343 | 0.106* | |
C41 | 1.2012 (6) | −0.2080 (5) | 0.7286 (3) | 0.0886 (17) | |
H41 | 1.2770 | −0.2062 | 0.6971 | 0.106* | |
C42 | 1.1431 (5) | −0.1001 (4) | 0.7529 (3) | 0.0686 (13) | |
H42 | 1.1806 | −0.0257 | 0.7382 | 0.082* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Fe | 0.0438 (3) | 0.0289 (3) | 0.0396 (3) | 0.0075 (2) | 0.0040 (2) | 0.00545 (19) |
O1 | 0.0523 (16) | 0.0539 (16) | 0.0604 (18) | 0.0033 (13) | 0.0096 (14) | 0.0044 (14) |
O2 | 0.0623 (17) | 0.0343 (13) | 0.0516 (16) | 0.0088 (12) | −0.0008 (13) | 0.0056 (11) |
O3 | 0.0483 (15) | 0.0395 (14) | 0.0496 (15) | 0.0072 (11) | 0.0036 (12) | 0.0044 (12) |
N1 | 0.0534 (19) | 0.0324 (15) | 0.0471 (18) | 0.0086 (14) | 0.0039 (15) | 0.0072 (13) |
N2 | 0.059 (2) | 0.0386 (16) | 0.0424 (17) | 0.0098 (15) | 0.0091 (15) | 0.0054 (14) |
N3 | 0.0519 (19) | 0.0393 (17) | 0.0439 (18) | 0.0114 (15) | 0.0047 (15) | 0.0027 (14) |
C1 | 0.054 (2) | 0.0336 (19) | 0.065 (3) | 0.0123 (18) | −0.006 (2) | 0.0040 (18) |
C2 | 0.050 (2) | 0.0339 (19) | 0.068 (3) | 0.0071 (17) | −0.004 (2) | 0.0069 (19) |
C3 | 0.051 (3) | 0.061 (3) | 0.095 (4) | 0.006 (2) | 0.002 (3) | 0.012 (3) |
C4 | 0.058 (3) | 0.060 (3) | 0.117 (5) | −0.004 (2) | −0.010 (3) | 0.017 (3) |
C5 | 0.068 (3) | 0.047 (3) | 0.105 (4) | 0.008 (2) | −0.029 (3) | −0.002 (3) |
C6 | 0.069 (3) | 0.041 (2) | 0.079 (3) | 0.021 (2) | −0.014 (2) | −0.001 (2) |
C7 | 0.066 (3) | 0.0358 (19) | 0.046 (2) | 0.0175 (19) | 0.000 (2) | 0.0028 (16) |
C8 | 0.066 (3) | 0.039 (2) | 0.047 (2) | 0.0129 (18) | 0.0143 (19) | 0.0051 (17) |
C9 | 0.063 (3) | 0.041 (2) | 0.047 (2) | 0.0123 (19) | 0.016 (2) | 0.0061 (17) |
C10 | 0.072 (3) | 0.055 (3) | 0.058 (3) | 0.004 (2) | 0.017 (2) | 0.015 (2) |
C11 | 0.093 (4) | 0.058 (3) | 0.069 (3) | −0.011 (3) | 0.023 (3) | −0.001 (2) |
C12 | 0.105 (4) | 0.041 (2) | 0.083 (3) | 0.010 (3) | 0.039 (3) | 0.009 (2) |
C13 | 0.103 (4) | 0.053 (3) | 0.088 (4) | 0.033 (3) | 0.022 (3) | 0.027 (3) |
C14 | 0.076 (3) | 0.055 (3) | 0.068 (3) | 0.016 (2) | 0.005 (2) | 0.017 (2) |
C15 | 0.055 (2) | 0.0370 (19) | 0.050 (2) | 0.0077 (17) | 0.0059 (18) | 0.0103 (17) |
C16 | 0.048 (2) | 0.037 (2) | 0.055 (2) | 0.0049 (17) | 0.0079 (19) | 0.0098 (17) |
C17 | 0.059 (3) | 0.045 (2) | 0.062 (3) | 0.0129 (19) | 0.006 (2) | 0.0025 (19) |
C18 | 0.071 (3) | 0.052 (3) | 0.082 (3) | 0.025 (2) | 0.006 (3) | 0.006 (2) |
C19 | 0.067 (3) | 0.062 (3) | 0.086 (4) | 0.027 (2) | −0.002 (3) | 0.019 (3) |
C20 | 0.070 (3) | 0.059 (3) | 0.060 (3) | 0.008 (2) | 0.001 (2) | 0.015 (2) |
C21 | 0.069 (3) | 0.045 (2) | 0.044 (2) | 0.008 (2) | 0.007 (2) | 0.0100 (17) |
C22 | 0.085 (3) | 0.054 (3) | 0.057 (3) | 0.018 (2) | 0.022 (2) | 0.003 (2) |
C23 | 0.051 (2) | 0.058 (3) | 0.060 (3) | 0.005 (2) | 0.010 (2) | 0.007 (2) |
C24 | 0.100 (4) | 0.097 (4) | 0.097 (4) | −0.036 (4) | 0.018 (3) | −0.018 (3) |
C25 | 0.127 (6) | 0.127 (6) | 0.166 (8) | −0.064 (5) | 0.045 (6) | −0.003 (6) |
C26 | 0.106 (5) | 0.149 (7) | 0.136 (7) | −0.017 (5) | 0.061 (5) | 0.042 (5) |
C27 | 0.097 (4) | 0.136 (6) | 0.074 (4) | 0.012 (4) | 0.034 (3) | 0.014 (4) |
C28 | 0.071 (3) | 0.072 (3) | 0.061 (3) | 0.002 (2) | 0.018 (2) | −0.003 (2) |
C29 | 0.055 (2) | 0.0351 (19) | 0.047 (2) | 0.0031 (17) | 0.0041 (18) | 0.0047 (16) |
C30 | 0.047 (2) | 0.044 (2) | 0.046 (2) | 0.0031 (17) | 0.0070 (18) | 0.0132 (17) |
C31 | 0.049 (2) | 0.060 (3) | 0.065 (3) | 0.007 (2) | 0.002 (2) | 0.010 (2) |
C32 | 0.056 (3) | 0.073 (3) | 0.082 (3) | −0.004 (2) | −0.009 (2) | 0.012 (3) |
C33 | 0.068 (3) | 0.060 (3) | 0.074 (3) | −0.009 (2) | −0.011 (2) | −0.003 (2) |
C34 | 0.069 (3) | 0.045 (2) | 0.066 (3) | −0.002 (2) | 0.004 (2) | 0.001 (2) |
C35 | 0.065 (3) | 0.0331 (19) | 0.051 (2) | 0.0102 (18) | 0.009 (2) | 0.0040 (17) |
C36 | 0.073 (3) | 0.048 (2) | 0.062 (3) | 0.023 (2) | −0.008 (2) | 0.005 (2) |
C37 | 0.050 (2) | 0.041 (2) | 0.051 (2) | 0.0124 (17) | 0.0021 (18) | 0.0083 (17) |
C38 | 0.066 (3) | 0.052 (2) | 0.071 (3) | 0.011 (2) | 0.018 (2) | 0.017 (2) |
C39 | 0.089 (4) | 0.040 (2) | 0.106 (4) | 0.012 (2) | 0.004 (3) | 0.023 (2) |
C40 | 0.103 (4) | 0.071 (3) | 0.097 (4) | 0.048 (3) | 0.014 (3) | 0.006 (3) |
C41 | 0.082 (4) | 0.097 (4) | 0.101 (4) | 0.043 (3) | 0.038 (3) | 0.025 (3) |
C42 | 0.056 (3) | 0.065 (3) | 0.093 (3) | 0.016 (2) | 0.019 (2) | 0.032 (3) |
Fe—O3 | 1.883 (3) | C18—C19 | 1.382 (6) |
Fe—O1 | 1.887 (3) | C18—H18 | 0.9300 |
Fe—O2 | 1.899 (2) | C19—C20 | 1.375 (6) |
Fe—N2 | 1.934 (3) | C19—H19 | 0.9300 |
Fe—N1 | 1.936 (3) | C20—H20 | 0.9300 |
Fe—N3 | 1.948 (3) | C21—H21 | 0.9300 |
O1—C2 | 1.306 (4) | C22—C23 | 1.506 (6) |
O2—C16 | 1.304 (4) | C22—H22A | 0.9700 |
O3—C30 | 1.314 (4) | C22—H22B | 0.9700 |
N1—C7 | 1.283 (5) | C23—C28 | 1.363 (6) |
N1—C8 | 1.485 (5) | C23—C24 | 1.383 (6) |
N2—C21 | 1.271 (4) | C24—C25 | 1.383 (9) |
N2—C22 | 1.497 (5) | C24—H24 | 0.9300 |
N3—C35 | 1.279 (5) | C25—C26 | 1.372 (9) |
N3—C36 | 1.488 (5) | C25—H25 | 0.9300 |
C1—C6 | 1.409 (6) | C26—C27 | 1.353 (8) |
C1—C2 | 1.413 (6) | C26—H26 | 0.9300 |
C1—C7 | 1.444 (6) | C27—C28 | 1.373 (7) |
C2—C3 | 1.406 (6) | C27—H27 | 0.9300 |
C3—C4 | 1.358 (6) | C28—H28 | 0.9300 |
C3—H3 | 0.9300 | C29—C34 | 1.394 (5) |
C4—C5 | 1.380 (7) | C29—C30 | 1.416 (5) |
C4—H4 | 0.9300 | C29—C35 | 1.440 (5) |
C5—C6 | 1.373 (7) | C30—C31 | 1.413 (5) |
C5—H5 | 0.9300 | C31—C32 | 1.371 (6) |
C6—H6 | 0.9300 | C31—H31 | 0.9300 |
C7—H7 | 0.9300 | C32—C33 | 1.396 (6) |
C8—C9 | 1.520 (5) | C32—H32 | 0.9300 |
C8—H8A | 0.9700 | C33—C34 | 1.362 (6) |
C8—H8B | 0.9700 | C33—H33 | 0.9300 |
C9—C10 | 1.369 (6) | C34—H34 | 0.9300 |
C9—C14 | 1.380 (5) | C35—H35 | 0.9300 |
C10—C11 | 1.402 (6) | C36—C37 | 1.499 (5) |
C10—H10 | 0.9300 | C36—H36A | 0.9700 |
C11—C12 | 1.362 (7) | C36—H36B | 0.9700 |
C11—H11 | 0.9300 | C37—C42 | 1.375 (6) |
C12—C13 | 1.354 (7) | C37—C38 | 1.385 (5) |
C12—H12 | 0.9300 | C38—C39 | 1.380 (6) |
C13—C14 | 1.390 (6) | C38—H38 | 0.9300 |
C13—H13 | 0.9300 | C39—C40 | 1.359 (7) |
C14—H14 | 0.9300 | C39—H39 | 0.9300 |
C15—C20 | 1.396 (5) | C40—C41 | 1.374 (7) |
C15—C16 | 1.406 (5) | C40—H40 | 0.9300 |
C15—C21 | 1.436 (5) | C41—C42 | 1.378 (6) |
C16—C17 | 1.418 (5) | C41—H41 | 0.9300 |
C17—C18 | 1.358 (6) | C42—H42 | 0.9300 |
C17—H17 | 0.9300 | ||
O3—Fe—O1 | 173.53 (12) | C17—C18—C19 | 121.7 (4) |
O3—Fe—O2 | 88.52 (11) | C17—C18—H18 | 119.1 |
O1—Fe—O2 | 89.71 (12) | C19—C18—H18 | 119.1 |
O3—Fe—N2 | 88.56 (12) | C20—C19—C18 | 118.6 (4) |
O1—Fe—N2 | 85.23 (13) | C20—C19—H19 | 120.7 |
O2—Fe—N2 | 90.60 (12) | C18—C19—H19 | 120.7 |
O3—Fe—N1 | 91.87 (12) | C19—C20—C15 | 121.5 (4) |
O1—Fe—N1 | 94.17 (13) | C19—C20—H20 | 119.3 |
O2—Fe—N1 | 84.64 (11) | C15—C20—H20 | 119.3 |
N2—Fe—N1 | 175.21 (12) | N2—C21—C15 | 125.5 (4) |
O3—Fe—N3 | 90.66 (12) | N2—C21—H21 | 117.2 |
O1—Fe—N3 | 91.47 (13) | C15—C21—H21 | 117.2 |
O2—Fe—N3 | 176.53 (12) | N2—C22—C23 | 114.6 (3) |
N2—Fe—N3 | 92.76 (12) | N2—C22—H22A | 108.6 |
N1—Fe—N3 | 92.01 (12) | C23—C22—H22A | 108.6 |
C2—O1—Fe | 125.9 (3) | N2—C22—H22B | 108.6 |
C16—O2—Fe | 120.7 (2) | C23—C22—H22B | 108.6 |
C30—O3—Fe | 119.9 (2) | H22A—C22—H22B | 107.6 |
C7—N1—C8 | 116.2 (3) | C28—C23—C24 | 118.8 (5) |
C7—N1—Fe | 122.3 (3) | C28—C23—C22 | 121.0 (4) |
C8—N1—Fe | 120.6 (2) | C24—C23—C22 | 120.1 (4) |
C21—N2—C22 | 117.7 (3) | C23—C24—C25 | 119.2 (6) |
C21—N2—Fe | 122.0 (3) | C23—C24—H24 | 120.4 |
C22—N2—Fe | 120.3 (2) | C25—C24—H24 | 120.4 |
C35—N3—C36 | 120.0 (3) | C26—C25—C24 | 121.0 (6) |
C35—N3—Fe | 122.2 (3) | C26—C25—H25 | 119.5 |
C36—N3—Fe | 117.7 (2) | C24—C25—H25 | 119.5 |
C6—C1—C2 | 119.2 (4) | C27—C26—C25 | 119.3 (6) |
C6—C1—C7 | 117.9 (4) | C27—C26—H26 | 120.3 |
C2—C1—C7 | 122.9 (4) | C25—C26—H26 | 120.3 |
O1—C2—C3 | 119.2 (4) | C26—C27—C28 | 120.2 (6) |
O1—C2—C1 | 123.0 (4) | C26—C27—H27 | 119.9 |
C3—C2—C1 | 117.8 (4) | C28—C27—H27 | 119.9 |
C4—C3—C2 | 121.4 (5) | C23—C28—C27 | 121.5 (5) |
C4—C3—H3 | 119.3 | C23—C28—H28 | 119.3 |
C2—C3—H3 | 119.3 | C27—C28—H28 | 119.3 |
C3—C4—C5 | 121.2 (5) | C34—C29—C30 | 119.9 (4) |
C3—C4—H4 | 119.4 | C34—C29—C35 | 120.1 (3) |
C5—C4—H4 | 119.4 | C30—C29—C35 | 119.9 (3) |
C6—C5—C4 | 119.3 (5) | O3—C30—C31 | 119.1 (3) |
C6—C5—H5 | 120.3 | O3—C30—C29 | 123.5 (3) |
C4—C5—H5 | 120.3 | C31—C30—C29 | 117.4 (4) |
C5—C6—C1 | 121.0 (5) | C32—C31—C30 | 120.6 (4) |
C5—C6—H6 | 119.5 | C32—C31—H31 | 119.7 |
C1—C6—H6 | 119.5 | C30—C31—H31 | 119.7 |
N1—C7—C1 | 126.9 (4) | C31—C32—C33 | 121.7 (4) |
N1—C7—H7 | 116.5 | C31—C32—H32 | 119.1 |
C1—C7—H7 | 116.5 | C33—C32—H32 | 119.1 |
N1—C8—C9 | 113.7 (3) | C34—C33—C32 | 118.3 (4) |
N1—C8—H8A | 108.8 | C34—C33—H33 | 120.8 |
C9—C8—H8A | 108.8 | C32—C33—H33 | 120.8 |
N1—C8—H8B | 108.8 | C33—C34—C29 | 122.0 (4) |
C9—C8—H8B | 108.8 | C33—C34—H34 | 119.0 |
H8A—C8—H8B | 107.7 | C29—C34—H34 | 119.0 |
C10—C9—C14 | 118.6 (4) | N3—C35—C29 | 125.5 (3) |
C10—C9—C8 | 121.5 (4) | N3—C35—H35 | 117.3 |
C14—C9—C8 | 119.8 (4) | C29—C35—H35 | 117.3 |
C9—C10—C11 | 120.6 (4) | N3—C36—C37 | 117.2 (3) |
C9—C10—H10 | 119.7 | N3—C36—H36A | 108.0 |
C11—C10—H10 | 119.7 | C37—C36—H36A | 108.0 |
C12—C11—C10 | 119.6 (5) | N3—C36—H36B | 108.0 |
C12—C11—H11 | 120.2 | C37—C36—H36B | 108.0 |
C10—C11—H11 | 120.2 | H36A—C36—H36B | 107.2 |
C13—C12—C11 | 120.5 (4) | C42—C37—C38 | 118.4 (4) |
C13—C12—H12 | 119.8 | C42—C37—C36 | 119.3 (4) |
C11—C12—H12 | 119.8 | C38—C37—C36 | 122.2 (4) |
C12—C13—C14 | 120.2 (5) | C39—C38—C37 | 120.8 (4) |
C12—C13—H13 | 119.9 | C39—C38—H38 | 119.6 |
C14—C13—H13 | 119.9 | C37—C38—H38 | 119.6 |
C9—C14—C13 | 120.5 (5) | C40—C39—C38 | 120.0 (4) |
C9—C14—H14 | 119.7 | C40—C39—H39 | 120.0 |
C13—C14—H14 | 119.7 | C38—C39—H39 | 120.0 |
C20—C15—C16 | 119.8 (4) | C39—C40—C41 | 120.1 (5) |
C20—C15—C21 | 119.6 (4) | C39—C40—H40 | 119.9 |
C16—C15—C21 | 120.1 (3) | C41—C40—H40 | 119.9 |
O2—C16—C15 | 124.1 (3) | C40—C41—C42 | 120.1 (5) |
O2—C16—C17 | 118.4 (3) | C40—C41—H41 | 120.0 |
C15—C16—C17 | 117.4 (3) | C42—C41—H41 | 120.0 |
C18—C17—C16 | 120.9 (4) | C37—C42—C41 | 120.7 (4) |
C18—C17—H17 | 119.6 | C37—C42—H42 | 119.7 |
C16—C17—H17 | 119.6 | C41—C42—H42 | 119.7 |
O3—Fe—O1—C2 | 134.2 (9) | C14—C9—C10—C11 | −1.3 (6) |
O2—Fe—O1—C2 | 60.1 (3) | C8—C9—C10—C11 | −177.3 (4) |
N2—Fe—O1—C2 | 150.7 (3) | C9—C10—C11—C12 | 0.6 (7) |
N1—Fe—O1—C2 | −24.5 (3) | C10—C11—C12—C13 | 0.6 (7) |
N3—Fe—O1—C2 | −116.7 (3) | C11—C12—C13—C14 | −1.0 (7) |
O3—Fe—O2—C16 | −46.1 (3) | C10—C9—C14—C13 | 0.9 (6) |
O1—Fe—O2—C16 | 127.7 (3) | C8—C9—C14—C13 | 177.0 (4) |
N2—Fe—O2—C16 | 42.4 (3) | C12—C13—C14—C9 | 0.2 (7) |
N1—Fe—O2—C16 | −138.1 (3) | Fe—O2—C16—C15 | −28.7 (5) |
N3—Fe—O2—C16 | −122 (2) | Fe—O2—C16—C17 | 153.8 (3) |
O1—Fe—O3—C30 | 63.8 (10) | C20—C15—C16—O2 | 179.7 (4) |
O2—Fe—O3—C30 | 138.0 (3) | C21—C15—C16—O2 | −8.4 (6) |
N2—Fe—O3—C30 | 47.4 (3) | C20—C15—C16—C17 | −2.7 (6) |
N1—Fe—O3—C30 | −137.4 (2) | C21—C15—C16—C17 | 169.1 (3) |
N3—Fe—O3—C30 | −45.4 (3) | O2—C16—C17—C18 | 179.8 (4) |
O3—Fe—N1—C7 | −158.8 (3) | C15—C16—C17—C18 | 2.2 (6) |
O1—Fe—N1—C7 | 18.9 (3) | C16—C17—C18—C19 | 0.7 (7) |
O2—Fe—N1—C7 | −70.4 (3) | C17—C18—C19—C20 | −3.0 (7) |
N2—Fe—N1—C7 | −63.8 (17) | C18—C19—C20—C15 | 2.3 (7) |
N3—Fe—N1—C7 | 110.5 (3) | C16—C15—C20—C19 | 0.5 (6) |
O3—Fe—N1—C8 | 9.6 (2) | C21—C15—C20—C19 | −171.3 (4) |
O1—Fe—N1—C8 | −172.7 (2) | C22—N2—C21—C15 | −169.7 (4) |
O2—Fe—N1—C8 | 98.0 (2) | Fe—N2—C21—C15 | 8.2 (6) |
N2—Fe—N1—C8 | 104.6 (16) | C20—C15—C21—N2 | −168.4 (4) |
N3—Fe—N1—C8 | −81.1 (2) | C16—C15—C21—N2 | 19.7 (6) |
O3—Fe—N2—C21 | 55.8 (3) | C21—N2—C22—C23 | 43.0 (5) |
O1—Fe—N2—C21 | −122.3 (3) | Fe—N2—C22—C23 | −135.0 (3) |
O2—Fe—N2—C21 | −32.7 (3) | N2—C22—C23—C28 | −128.0 (4) |
N1—Fe—N2—C21 | −39.3 (18) | N2—C22—C23—C24 | 53.2 (6) |
N3—Fe—N2—C21 | 146.4 (3) | C28—C23—C24—C25 | 0.7 (9) |
O3—Fe—N2—C22 | −126.2 (3) | C22—C23—C24—C25 | 179.6 (6) |
O1—Fe—N2—C22 | 55.6 (3) | C23—C24—C25—C26 | −1.5 (12) |
O2—Fe—N2—C22 | 145.3 (3) | C24—C25—C26—C27 | 1.2 (13) |
N1—Fe—N2—C22 | 138.7 (16) | C25—C26—C27—C28 | −0.2 (12) |
N3—Fe—N2—C22 | −35.6 (3) | C24—C23—C28—C27 | 0.2 (8) |
O3—Fe—N3—C35 | 29.1 (3) | C22—C23—C28—C27 | −178.6 (5) |
O1—Fe—N3—C35 | −144.7 (3) | C26—C27—C28—C23 | −0.5 (9) |
O2—Fe—N3—C35 | 105 (2) | Fe—O3—C30—C31 | −144.6 (3) |
N2—Fe—N3—C35 | −59.4 (3) | Fe—O3—C30—C29 | 36.7 (4) |
N1—Fe—N3—C35 | 121.0 (3) | C34—C29—C30—O3 | 178.5 (4) |
O3—Fe—N3—C36 | −147.6 (3) | C35—C29—C30—O3 | 2.1 (6) |
O1—Fe—N3—C36 | 38.6 (3) | C34—C29—C30—C31 | −0.2 (5) |
O2—Fe—N3—C36 | −71 (2) | C35—C29—C30—C31 | −176.6 (4) |
N2—Fe—N3—C36 | 123.9 (3) | O3—C30—C31—C32 | −179.9 (4) |
N1—Fe—N3—C36 | −55.7 (3) | C29—C30—C31—C32 | −1.1 (6) |
Fe—O1—C2—C3 | −163.3 (3) | C30—C31—C32—C33 | 0.9 (7) |
Fe—O1—C2—C1 | 18.6 (5) | C31—C32—C33—C34 | 0.8 (7) |
C6—C1—C2—O1 | −179.8 (3) | C32—C33—C34—C29 | −2.2 (7) |
C7—C1—C2—O1 | −0.1 (6) | C30—C29—C34—C33 | 2.0 (6) |
C6—C1—C2—C3 | 2.1 (5) | C35—C29—C34—C33 | 178.4 (4) |
C7—C1—C2—C3 | −178.2 (3) | C36—N3—C35—C29 | 174.3 (4) |
O1—C2—C3—C4 | 179.9 (4) | Fe—N3—C35—C29 | −2.4 (5) |
C1—C2—C3—C4 | −1.9 (6) | C34—C29—C35—N3 | 162.9 (4) |
C2—C3—C4—C5 | 0.1 (7) | C30—C29—C35—N3 | −20.7 (6) |
C3—C4—C5—C6 | 1.4 (7) | C35—N3—C36—C37 | 28.5 (6) |
C4—C5—C6—C1 | −1.2 (6) | Fe—N3—C36—C37 | −154.7 (3) |
C2—C1—C6—C5 | −0.6 (6) | N3—C36—C37—C42 | 94.3 (5) |
C7—C1—C6—C5 | 179.6 (3) | N3—C36—C37—C38 | −89.2 (5) |
C8—N1—C7—C1 | −177.2 (3) | C42—C37—C38—C39 | −0.7 (6) |
Fe—N1—C7—C1 | −8.3 (5) | C36—C37—C38—C39 | −177.3 (4) |
C6—C1—C7—N1 | 174.7 (3) | C37—C38—C39—C40 | 0.2 (7) |
C2—C1—C7—N1 | −5.1 (6) | C38—C39—C40—C41 | 0.1 (8) |
C7—N1—C8—C9 | −110.8 (4) | C39—C40—C41—C42 | 0.1 (9) |
Fe—N1—C8—C9 | 80.2 (4) | C38—C37—C42—C41 | 0.9 (7) |
N1—C8—C9—C10 | −115.1 (4) | C36—C37—C42—C41 | 177.6 (4) |
N1—C8—C9—C14 | 69.0 (5) | C40—C41—C42—C37 | −0.7 (8) |
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8A···O3 | 0.97 | 2.34 | 2.830 (2) | 111 |
C22—H22B···O1 | 0.97 | 2.52 | 2.978 (2) | 109 |
C22—H22B···N3 | 0.97 | 2.59 | 3.018 (2) | 107 |
C36—H36B···O1 | 0.97 | 2.29 | 2.938 (2) | 123 |
Experimental details
Crystal data | |
Chemical formula | [Fe(C14H12NO)3] |
Mr | 686.59 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 9.3470 (8), 10.9248 (13), 16.7702 (19) |
α, β, γ (°) | 95.42 (3), 96.47 (3), 93.88 (3) |
V (Å3) | 1688.6 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.49 |
Crystal size (mm) | 0.40 × 0.30 × 0.20 |
Data collection | |
Diffractometer | Bruker APEX area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.828, 0.908 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7053, 6624, 4330 |
Rint | 0.035 |
(sin θ/λ)max (Å−1) | 0.616 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.057, 0.152, 1.04 |
No. of reflections | 6624 |
No. of parameters | 442 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.59, −0.52 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8A···O3 | 0.97 | 2.34 | 2.830 (2) | 111 |
C22—H22B···O1 | 0.97 | 2.52 | 2.978 (2) | 109 |
C22—H22B···N3 | 0.97 | 2.59 | 3.018 (2) | 107 |
C36—H36B···O1 | 0.97 | 2.29 | 2.938 (2) | 123 |
Acknowledgements
This work was supported by the National Natural Science Foundation of China (No. 30572073), the Natural Science Foundation of Jiangsu Province of China (No. DK2005428), the Medical Science and Technology Development Foundation, Jiangsu Province Department of Health (No. K200402), and the Social Development Foundation of Xuzhou (No. X2003025).
References
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Due to its interesting physical and biological properties, many iron complexes with amines or imines have been structurally studied (Liu et al., 2004; You & Zhu, 2004; You et al.,2004, 2005; Zhu, Xia et al., 2003; Zhu, Zeng et al., 2003). We report here the title structure of (I). Compound (I) is an electronically neutral mononuclear iron (III) compound (Fig. 1). In the complex the central iron(III) atom is six coordinated by three nitrogen atoms and three oxygen atoms from three Schiff base ligands. In the crystal structure, (I) is stabilized by intramolecular C—H···O and C—H···N hydrogen bonds.