metal-organic compounds
The FeIII atom in the title complex, [Fe(HL)Cl2(CH3OH)]·CH3OH, [H2L = 3-methoxysalicylaldehyde (4-methoxybenzoyl)hydrazone, C16H15N2O4], is coordinated by two O atoms and one N atom of the tridentate hydrazone ligand, two chloride anions and one methanol molecule, thus defining a distorted octahedral geometry. A chain structure is constructed by hydrogen-bond interactions.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680400950X/hb6037sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680400950X/hb6037Isup2.hkl |
CCDC reference: 239087
Computing details top
Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
Dichloro(methanol-κO)[3-methoxysalicylaldehyde
(4-methoxybenzoyl)hydrazonato-κ3O,O',N]iron(III)
methanol solvate top
Crystal data top
[Fe(C16H15N2O4)Cl2(CH4O)]·CH4O | F(000) = 1012 |
Mr = 490.13 | Dx = 1.526 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 12723 reflections |
a = 17.226 (3) Å | θ = 3.0–27.4° |
b = 10.622 (2) Å | µ = 0.99 mm−1 |
c = 12.096 (2) Å | T = 293 K |
β = 105.42 (3)° | Prism, black |
V = 2133.6 (7) Å3 | 0.37 × 0.23 × 0.16 mm |
Z = 4 |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 4757 independent reflections |
Radiation source: fine-focus sealed tube | 2849 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.081 |
Detector resolution: 10 pixels mm-1 | θmax = 27.5°, θmin = 3.1° |
ω scans | h = −22→22 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −13→13 |
Tmin = 0.710, Tmax = 0.857 | l = −15→15 |
12872 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)] = 0.065 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.187 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0998P)2] where P = (Fo2 + 2Fc2)/3 |
4757 reflections | (Δ/σ)max = 0.001 |
272 parameters | Δρmax = 0.64 e Å−3 |
3 restraints | Δρmin = −0.38 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Fe1 | 0.74674 (4) | 0.19978 (6) | 0.03200 (5) | 0.0353 (2) | |
Cl1 | 0.66140 (8) | 0.2019 (1) | −0.14449 (9) | 0.0484 (3) | |
Cl2 | 0.82587 (9) | 0.0399 (1) | −0.0013 (1) | 0.0569 (4) | |
N1 | 0.8045 (2) | 0.1964 (3) | 0.2116 (3) | 0.0318 (8) | |
N2 | 0.7746 (2) | 0.1027 (4) | 0.2665 (3) | 0.0337 (8) | |
O1 | 0.8168 (2) | 0.3366 (3) | 0.0284 (2) | 0.0385 (8) | |
O2 | 0.6852 (2) | 0.0710 (3) | 0.0999 (2) | 0.0403 (8) | |
O3 | 0.8806 (2) | 0.5276 (3) | −0.0447 (3) | 0.0507 (9) | |
O4 | 0.5642 (2) | −0.3237 (4) | 0.4002 (3) | 0.060 (1) | |
O5 | 0.6747 (2) | 0.3394 (3) | 0.0784 (3) | 0.0440 (8) | |
O6 | 0.7247 (3) | −0.0239 (4) | −0.2728 (3) | 0.067 (1) | |
C1 | 0.8706 (3) | 0.3970 (4) | 0.1052 (4) | 0.035 (1) | |
C2 | 0.9072 (3) | 0.5029 (5) | 0.0695 (4) | 0.040 (1) | |
C3 | 0.9633 (3) | 0.5714 (6) | 0.1460 (5) | 0.057 (2) | |
C4 | 0.9881 (3) | 0.5378 (6) | 0.2600 (5) | 0.058 (2) | |
C5 | 0.9543 (3) | 0.4356 (5) | 0.2970 (4) | 0.049 (1) | |
C6 | 0.8962 (3) | 0.3649 (4) | 0.2229 (4) | 0.037 (1) | |
C7 | 0.8595 (3) | 0.2657 (4) | 0.2702 (4) | 0.033 (1) | |
C8 | 0.9021 (4) | 0.6450 (6) | −0.0862 (5) | 0.062 (2) | |
C9 | 0.7110 (3) | 0.0444 (4) | 0.2041 (3) | 0.033 (1) | |
C10 | 0.6744 (3) | −0.0524 (4) | 0.2566 (4) | 0.032 (1) | |
C11 | 0.6840 (3) | −0.0590 (5) | 0.3744 (4) | 0.044 (1) | |
C12 | 0.6455 (3) | −0.1493 (5) | 0.4170 (4) | 0.053 (1) | |
C13 | 0.5987 (3) | −0.2382 (5) | 0.3477 (4) | 0.042 (1) | |
C14 | 0.5876 (3) | −0.2316 (5) | 0.2308 (4) | 0.040 (1) | |
C15 | 0.6239 (3) | −0.1386 (4) | 0.1853 (4) | 0.036 (1) | |
C16 | 0.5211 (4) | −0.4244 (6) | 0.3362 (6) | 0.070 (2) | |
C17 | 0.5928 (3) | 0.3411 (6) | 0.0542 (5) | 0.063 (2) | |
C18 | 0.7738 (4) | −0.1279 (6) | −0.2682 (6) | 0.066 (2) | |
H3 | 0.9853 | 0.6424 | 0.1210 | 0.068* | |
H4 | 1.0275 | 0.5844 | 0.3112 | 0.070* | |
H5 | 0.9709 | 0.4131 | 0.3740 | 0.059* | |
H7 | 0.8772 | 0.2513 | 0.3487 | 0.039* | |
H8A | 0.8796 | 0.6496 | −0.1677 | 0.094* | |
H8B | 0.9597 | 0.6514 | −0.0688 | 0.094* | |
H8C | 0.8815 | 0.7129 | −0.0500 | 0.094* | |
H11 | 0.7169 | −0.0016 | 0.4233 | 0.053* | |
H12 | 0.6506 | −0.1515 | 0.4955 | 0.063* | |
H14 | 0.5554 | −0.2906 | 0.1830 | 0.048* | |
H15 | 0.6149 | −0.1326 | 0.1062 | 0.043* | |
H16A | 0.5004 | −0.4778 | 0.3858 | 0.105* | |
H16B | 0.5563 | −0.4722 | 0.3026 | 0.105* | |
H16C | 0.4772 | −0.3918 | 0.2765 | 0.105* | |
H17A | 0.5758 | 0.4159 | 0.0859 | 0.095* | |
H17B | 0.5746 | 0.2683 | 0.0872 | 0.095* | |
H17C | 0.5702 | 0.3404 | −0.0274 | 0.095* | |
H18A | 0.8274 | −0.1081 | −0.2237 | 0.099* | |
H18B | 0.7748 | −0.1511 | −0.3445 | 0.099* | |
H18C | 0.7532 | −0.1968 | −0.2331 | 0.099* | |
H19 | 0.798 (3) | 0.091 (5) | 0.342 (1) | 0.051* | |
H20 | 0.696 (3) | 0.405 (3) | 0.112 (4) | 0.066* | |
H21 | 0.726 (5) | 0.034 (5) | −0.224 (5) | 0.101* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Fe1 | 0.0367 (4) | 0.0445 (4) | 0.0222 (3) | −0.0085 (3) | 0.0036 (3) | 0.0024 (3) |
Cl1 | 0.0499 (8) | 0.0637 (9) | 0.0255 (5) | −0.0080 (6) | −0.0005 (5) | 0.0028 (5) |
Cl2 | 0.0620 (9) | 0.0632 (9) | 0.0429 (7) | 0.0120 (7) | 0.0093 (6) | −0.0053 (6) |
N1 | 0.038 (2) | 0.034 (2) | 0.024 (2) | −0.001 (2) | 0.010 (2) | 0.000 (2) |
N2 | 0.033 (2) | 0.042 (2) | 0.024 (2) | −0.001 (2) | 0.004 (2) | 0.004 (2) |
O1 | 0.043 (2) | 0.044 (2) | 0.025 (1) | −0.010 (1) | 0.004 (1) | 0.003 (1) |
O2 | 0.042 (2) | 0.051 (2) | 0.024 (1) | −0.012 (2) | 0.003 (1) | 0.004 (1) |
O3 | 0.053 (2) | 0.059 (2) | 0.037 (2) | −0.017 (2) | 0.006 (2) | 0.010 (2) |
O4 | 0.069 (3) | 0.061 (3) | 0.048 (2) | −0.030 (2) | 0.011 (2) | 0.012 (2) |
O5 | 0.036 (2) | 0.054 (2) | 0.040 (2) | −0.002 (2) | 0.006 (2) | −0.003 (2) |
O6 | 0.082 (3) | 0.056 (3) | 0.058 (2) | 0.013 (2) | 0.010 (2) | 0.002 (2) |
C1 | 0.031 (2) | 0.041 (3) | 0.032 (2) | −0.001 (2) | 0.007 (2) | −0.001 (2) |
C2 | 0.031 (3) | 0.047 (3) | 0.039 (2) | −0.005 (2) | 0.005 (2) | 0.005 (2) |
C3 | 0.051 (3) | 0.061 (4) | 0.053 (3) | −0.019 (3) | 0.005 (3) | 0.008 (3) |
C4 | 0.042 (3) | 0.068 (4) | 0.056 (3) | −0.021 (3) | −0.003 (3) | −0.011 (3) |
C5 | 0.045 (3) | 0.059 (3) | 0.039 (3) | −0.011 (2) | 0.005 (2) | 0.000 (2) |
C6 | 0.036 (3) | 0.036 (2) | 0.036 (2) | −0.002 (2) | 0.007 (2) | −0.003 (2) |
C7 | 0.029 (2) | 0.041 (3) | 0.026 (2) | 0.007 (2) | 0.003 (2) | 0.002 (2) |
C8 | 0.066 (4) | 0.058 (4) | 0.061 (4) | −0.007 (3) | 0.014 (3) | 0.017 (3) |
C9 | 0.040 (3) | 0.031 (2) | 0.028 (2) | 0.001 (2) | 0.010 (2) | 0.000 (2) |
C10 | 0.033 (2) | 0.033 (2) | 0.028 (2) | 0.004 (2) | 0.008 (2) | 0.002 (2) |
C11 | 0.054 (3) | 0.051 (3) | 0.027 (2) | −0.016 (2) | 0.010 (2) | −0.008 (2) |
C12 | 0.064 (4) | 0.066 (4) | 0.027 (2) | −0.022 (3) | 0.010 (2) | 0.004 (2) |
C13 | 0.037 (3) | 0.046 (3) | 0.043 (3) | −0.001 (2) | 0.009 (2) | 0.007 (2) |
C14 | 0.040 (3) | 0.039 (3) | 0.035 (2) | −0.004 (2) | 0.000 (2) | −0.004 (2) |
C15 | 0.033 (3) | 0.043 (3) | 0.027 (2) | 0.002 (2) | 0.002 (2) | −0.003 (2) |
C16 | 0.066 (4) | 0.060 (4) | 0.079 (4) | −0.029 (3) | 0.008 (4) | 0.009 (3) |
C17 | 0.039 (3) | 0.102 (5) | 0.050 (3) | 0.008 (3) | 0.012 (3) | 0.001 (3) |
C18 | 0.047 (4) | 0.055 (4) | 0.086 (4) | −0.001 (3) | 0.002 (3) | −0.003 (3) |
Geometric parameters (Å, º) top
Fe1—Cl1 | 2.247 (2) | C5—C6 | 1.375 (7) |
Fe1—Cl2 | 2.280 (2) | C5—H5 | 0.9300 |
Fe1—N1 | 2.135 (4) | C6—C7 | 1.425 (6) |
Fe1—O1 | 1.897 (3) | C7—H7 | 0.9300 |
Fe1—O2 | 2.033 (3) | C8—H8A | 0.9600 |
Fe1—O5 | 2.104 (4) | C8—H8B | 0.9600 |
N1—N2 | 1.371 (5) | C8—H8C | 0.9600 |
N1—C7 | 1.259 (6) | C9—C10 | 1.439 (6) |
N2—C9 | 1.309 (6) | C10—C11 | 1.392 (6) |
O1—C1 | 1.294 (5) | C10—C15 | 1.393 (6) |
O2—C9 | 1.253 (5) | C11—C12 | 1.345 (7) |
N2—H19 | 0.903 (17) | C11—H11 | 0.9300 |
O3—C2 | 1.360 (5) | C12—C13 | 1.373 (7) |
O3—C8 | 1.430 (6) | C12—H12 | 0.9300 |
O4—C13 | 1.335 (6) | C13—C14 | 1.377 (7) |
O4—C16 | 1.411 (6) | C14—C15 | 1.361 (7) |
O5—C17 | 1.362 (6) | C14—H14 | 0.9300 |
O5—H20 | 0.84 (4) | C15—H15 | 0.9300 |
O6—C18 | 1.383 (7) | C16—H16A | 0.9600 |
O6—H21 | 0.85 (6) | C16—H16B | 0.9600 |
C1—C2 | 1.412 (6) | C16—H16C | 0.9600 |
C1—C6 | 1.415 (6) | C17—H17A | 0.9600 |
C2—C3 | 1.358 (7) | C17—H17B | 0.9600 |
C3—C4 | 1.378 (7) | C17—H17C | 0.9600 |
C3—H3 | 0.9300 | C18—H18A | 0.9600 |
C4—C5 | 1.362 (7) | C18—H18B | 0.9600 |
C4—H4 | 0.9300 | C18—H18C | 0.9600 |
Cl1—Fe1—Cl2 | 96.34 (6) | C3—C4—H4 | 120.4 |
N1—Fe1—Cl1 | 167.6 (1) | C4—C3—H3 | 119.4 |
N1—Fe1—Cl2 | 91.6 (1) | C4—C5—C6 | 121.4 (5) |
O1—Fe1—Cl1 | 103.3 (1) | C4—C5—H5 | 119.3 |
O1—Fe1—Cl2 | 98.8 (1) | C5—C4—C3 | 119.3 (5) |
O1—Fe1—N1 | 84.8 (1) | C5—C4—H4 | 120.4 |
O1—Fe1—O2 | 158.2 (1) | C5—C6—C1 | 120.1 (4) |
O1—Fe1—O5 | 83.7 (1) | C5—C6—C7 | 117.8 (4) |
O2—Fe1—Cl1 | 96.35 (9) | C6—C5—H5 | 119.3 |
O2—Fe1—Cl2 | 88.3 (1) | C6—C7—H7 | 118.2 |
O2—Fe1—N1 | 74.3 (1) | C7—N1—Fe1 | 129.8 (3) |
O2—Fe1—O5 | 87.6 (1) | C7—N1—N2 | 118.3 (4) |
O5—Fe1—Cl1 | 87.9 (1) | C9—N2—N1 | 115.4 (3) |
O5—Fe1—Cl2 | 174.4 (1) | C9—N2—H19 | 127 (3) |
O5—Fe1—N1 | 83.6 (1) | C9—O2—Fe1 | 118.3 (3) |
Fe1—O5—H20 | 120 (4) | C10—C11—H11 | 120.3 |
N1—N2—H19 | 118 (3) | C10—C15—H15 | 119.8 |
N1—C7—C6 | 123.6 (4) | C11—C10—C9 | 122.7 (4) |
N1—C7—H7 | 118.2 | C11—C10—C15 | 119.0 (4) |
N2—N1—Fe1 | 111.8 (3) | C11—C12—C13 | 121.7 (4) |
N2—C9—C10 | 118.8 (4) | C11—C12—H12 | 119.2 |
O1—C1—C2 | 117.9 (4) | C12—C11—C10 | 119.5 (5) |
O1—C1—C6 | 125.1 (4) | C12—C11—H11 | 120.3 |
O2—C9—N2 | 119.5 (4) | C12—C13—C14 | 119.4 (5) |
O2—C9—C10 | 121.6 (4) | C13—O4—C16 | 119.4 (4) |
O3—C2—C1 | 114.0 (4) | C13—C12—H12 | 119.2 |
O3—C8—H8A | 109.5 | C13—C14—H14 | 120.0 |
O3—C8—H8B | 109.5 | C14—C15—C10 | 120.4 (4) |
O3—C8—H8C | 109.5 | C14—C15—H15 | 119.8 |
O4—C13—C12 | 116.2 (4) | C15—C10—C9 | 118.2 (4) |
O4—C13—C14 | 124.4 (5) | C15—C14—C13 | 119.9 (5) |
O4—C16—H16A | 109.5 | C15—C14—H14 | 120.0 |
O4—C16—H16B | 109.5 | C17—O5—Fe1 | 127.1 (4) |
O4—C16—H16C | 109.5 | C17—O5—H20 | 113 (4) |
O5—C17—H17A | 109.5 | C18—O6—H21 | 130 (5) |
O5—C17—H17B | 109.5 | H8A—C8—H8B | 109.5 |
O5—C17—H17C | 109.5 | H8A—C8—H8C | 109.5 |
O6—C18—H18A | 109.5 | H8B—C8—H8C | 109.5 |
O6—C18—H18B | 109.5 | H16A—C16—H16B | 109.5 |
O6—C18—H18C | 109.5 | H16A—C16—H16C | 109.5 |
C1—O1—Fe1 | 134.5 (3) | H16B—C16—H16C | 109.5 |
C1—C6—C7 | 122.0 (4) | H17A—C17—H17B | 109.5 |
C2—O3—C8 | 118.4 (4) | H17A—C17—H17C | 109.5 |
C2—C1—C6 | 117.0 (4) | H17B—C17—H17C | 109.5 |
C2—C3—C4 | 121.3 (5) | H18A—C18—H18B | 109.5 |
C2—C3—H3 | 119.4 | H18A—C18—H18C | 109.5 |
C3—C2—O3 | 125.1 (4) | H18B—C18—H18C | 109.5 |
C3—C2—C1 | 120.9 (4) | ||
Fe1—N1—N2—C9 | −8.3 (5) | O2—C9—C10—C11 | −159.8 (5) |
Fe1—N1—C7—C6 | −0.9 (7) | O2—C9—C10—C15 | 16.8 (7) |
Fe1—O1—C1—C2 | −175.1 (3) | O3—C2—C3—C4 | −178.4 (5) |
Fe1—O1—C1—C6 | 5.2 (7) | O4—C13—C14—C15 | 178.3 (5) |
Fe1—O2—C9—N2 | 2.2 (6) | O5—Fe1—N1—C7 | −83.8 (4) |
Fe1—O2—C9—C10 | −175.4 (3) | O5—Fe1—N1—N2 | 96.2 (3) |
Cl1—Fe1—N1—N2 | 49.1 (7) | O5—Fe1—O1—C1 | 81.6 (4) |
Cl1—Fe1—N1—C7 | −130.9 (5) | O5—Fe1—O2—C9 | −89.2 (3) |
Cl1—Fe1—O1—C1 | 167.9 (4) | C1—C2—C3—C4 | 2.1 (9) |
Cl1—Fe1—O2—C9 | −176.8 (3) | C1—C6—C7—N1 | 2.9 (7) |
Cl2—Fe1—N1—N2 | −80.9 (3) | C2—C1—C6—C5 | 0.0 (7) |
Cl2—Fe1—N1—C7 | 99.1 (4) | C2—C1—C6—C7 | 175.4 (4) |
Cl2—Fe1—O1—C1 | −93.4 (4) | C2—C3—C4—C5 | −1.6 (9) |
Cl2—Fe1—O2—C9 | 87.0 (3) | C3—C4—C5—C6 | 0.3 (9) |
N1—Fe1—O1—C1 | −2.5 (4) | C4—C5—C6—C1 | 0.5 (8) |
N1—Fe1—O2—C9 | −5.1 (3) | C4—C5—C6—C7 | −175.1 (5) |
N1—Fe1—O5—C17 | −125.6 (4) | C5—C6—C7—N1 | 178.4 (5) |
N1—N2—C9—O2 | 4.4 (6) | C6—C1—C2—O3 | 179.2 (4) |
N1—N2—C9—C10 | −177.9 (4) | C6—C1—C2—C3 | −1.2 (7) |
N2—N1—C7—C6 | 179.1 (4) | C7—N1—N2—C9 | 171.7 (4) |
N2—C9—C10—C11 | 22.6 (7) | C8—O3—C2—C3 | −11.1 (8) |
N2—C9—C10—C15 | −160.8 (4) | C8—O3—C2—C1 | 168.5 (4) |
O1—Fe1—N1—C7 | 0.4 (4) | C9—C10—C11—C12 | 177.4 (5) |
O1—Fe1—N1—N2 | −179.6 (3) | C9—C10—C15—C14 | −179.8 (4) |
O1—Fe1—O2—C9 | −22.7 (6) | C10—C11—C12—C13 | 2.3 (9) |
O1—Fe1—O5—C17 | 149.0 (4) | C11—C12—C13—O4 | 179.2 (5) |
O1—C1—C2—O3 | −0.5 (6) | C11—C12—C13—C14 | −3.3 (9) |
O1—C1—C2—C3 | 179.1 (5) | C11—C10—C15—C14 | −3.1 (7) |
O1—C1—C6—C5 | 179.6 (5) | C12—C13—C14—C15 | 1.0 (8) |
O1—C1—C6—C7 | −4.9 (7) | C13—C14—C15—C10 | 2.1 (7) |
O2—Fe1—N1—C7 | −173.1 (4) | C15—C10—C11—C12 | 0.9 (8) |
O2—Fe1—N1—N2 | 6.9 (3) | C16—O4—C13—C12 | −174.5 (5) |
O2—Fe1—O1—C1 | 14.4 (7) | C16—O4—C13—C14 | 8.1 (8) |
O2—Fe1—O5—C17 | −51.1 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H19···O1i | 0.90 (2) | 2.33 (3) | 3.123 (4) | 148 (4) |
N2—H19···O3i | 0.90 (2) | 2.11 (3) | 2.872 (5) | 142 (4) |
O5—H20···O6i | 0.84 (4) | 1.84 (2) | 2.646 (5) | 158 (6) |
O6—H21···Cl1 | 0.85 (6) | 2.43 (4) | 3.201 (4) | 151 (7) |
O6—H21···Cl2 | 0.85 (6) | 2.79 (6) | 3.352 (5) | 126 (6) |
Symmetry code: (i) x, −y+1/2, z+1/2. |