metal-organic compounds
In the crystal structure of the methanol-coordinated mononuclear title compound, [Fe(C13H11N2O)Cl2(CH4O)], the FeIII atom is six-coordinate in an octahedral environment and the Cl atoms are cis to each other. Hydrogen bonds between the hydroxyl group of the methanol ligand and the Cl atom of an adjacent molecule lead to the formation of a chain that runs along the b axis of the orthorhombic unit cell.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805033143/bt6761sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805033143/bt6761Isup2.hkl |
CCDC reference: 289658
Computing details top
Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; 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.
Crystal data top
[Fe(C13H11N2O)Cl2(CH4O)] | F(000) = 756 |
Mr = 370.03 | Dx = 1.566 Mg m−3 |
Orthorhombic, Pca21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2ac | Cell parameters from 3270 reflections |
a = 19.428 (1) Å | θ = 2.5–25.6° |
b = 7.0016 (5) Å | µ = 1.31 mm−1 |
c = 11.5352 (8) Å | T = 295 K |
V = 1569.13 (19) Å3 | Block, purple |
Z = 4 | 0.26 × 0.14 × 0.10 mm |
Data collection top
Bruker APEX-II area-detector diffractometer | 3571 independent reflections |
Radiation source: fine-focus sealed tube | 3144 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
φ and ω scans | θmax = 27.5°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −25→25 |
Tmin = 0.486, Tmax = 0.881 | k = −6→9 |
9057 measured reflections | l = −14→14 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.025 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.062 | w = 1/[σ2(Fo2) + (0.0292P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.96 | (Δ/σ)max = 0.001 |
3571 reflections | Δρmax = 0.21 e Å−3 |
195 parameters | Δρmin = −0.20 e Å−3 |
2 restraints | Absolute structure: Flack (1983), with 1679 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.00 (1) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Fe1 | 0.44562 (1) | 0.84686 (4) | 0.50000 (3) | 0.03036 (8) | |
Cl1 | 0.38263 (3) | 1.00791 (8) | 0.36332 (5) | 0.0409 (1) | |
Cl2 | 0.41597 (3) | 0.53594 (7) | 0.44195 (6) | 0.0460 (2) | |
O1 | 0.5327 (1) | 0.8572 (2) | 0.4274 (2) | 0.0459 (4) | |
O2 | 0.4602 (1) | 1.1357 (2) | 0.5723 (2) | 0.0502 (5) | |
N1 | 0.4966 (1) | 0.7517 (3) | 0.6504 (2) | 0.0324 (4) | |
N2 | 0.3636 (1) | 0.8275 (3) | 0.6263 (2) | 0.0352 (4) | |
C1 | 0.5956 (1) | 0.7920 (3) | 0.4554 (2) | 0.0383 (5) | |
C2 | 0.6474 (1) | 0.8032 (3) | 0.3728 (3) | 0.0496 (6) | |
C3 | 0.7141 (1) | 0.7437 (4) | 0.4010 (3) | 0.0597 (9) | |
C4 | 0.7288 (1) | 0.6713 (4) | 0.5093 (4) | 0.0641 (8) | |
C5 | 0.6779 (1) | 0.6550 (3) | 0.5898 (3) | 0.0549 (7) | |
C6 | 0.6098 (1) | 0.7169 (3) | 0.5656 (2) | 0.0373 (5) | |
C7 | 0.5600 (1) | 0.7016 (3) | 0.6567 (2) | 0.0365 (5) | |
C8 | 0.4548 (1) | 0.7303 (4) | 0.7556 (2) | 0.0455 (6) | |
C9 | 0.3796 (1) | 0.7534 (3) | 0.7298 (2) | 0.0360 (5) | |
C10 | 0.3300 (1) | 0.7039 (3) | 0.8102 (3) | 0.0492 (6) | |
C11 | 0.2616 (1) | 0.7375 (4) | 0.7837 (3) | 0.0551 (8) | |
C12 | 0.2451 (1) | 0.8197 (4) | 0.6791 (3) | 0.0556 (7) | |
C13 | 0.2967 (1) | 0.8611 (3) | 0.6030 (2) | 0.0457 (6) | |
C14 | 0.5206 (2) | 1.2127 (4) | 0.6220 (3) | 0.073 (1) | |
H2O | 0.441 (2) | 1.215 (4) | 0.529 (3) | 0.09 (1)* | |
H2 | 0.6379 | 0.8501 | 0.2991 | 0.060* | |
H3 | 0.7489 | 0.7532 | 0.3460 | 0.072* | |
H4 | 0.7734 | 0.6337 | 0.5273 | 0.077* | |
H5 | 0.6879 | 0.6025 | 0.6619 | 0.066* | |
H7 | 0.5750 | 0.6509 | 0.7268 | 0.044* | |
H8A | 0.4687 | 0.8253 | 0.8122 | 0.055* | |
H8B | 0.4628 | 0.6051 | 0.7890 | 0.055* | |
H10 | 0.3423 | 0.6492 | 0.8807 | 0.059* | |
H11 | 0.2272 | 0.7048 | 0.8361 | 0.066* | |
H12 | 0.1996 | 0.8466 | 0.6605 | 0.067* | |
H13 | 0.2852 | 0.9149 | 0.5318 | 0.055* | |
H14A | 0.5097 | 1.2703 | 0.6952 | 0.110* | |
H14B | 0.5395 | 1.3075 | 0.5710 | 0.110* | |
H14C | 0.5537 | 1.1126 | 0.6335 | 0.110* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Fe1 | 0.0286 (1) | 0.0328 (1) | 0.0297 (1) | 0.0013 (1) | 0.0007 (2) | 0.0022 (1) |
Cl1 | 0.0365 (3) | 0.0468 (3) | 0.0394 (3) | 0.0015 (2) | −0.0056 (2) | 0.0086 (2) |
Cl2 | 0.0589 (4) | 0.0345 (3) | 0.0447 (3) | 0.0023 (3) | −0.0020 (3) | −0.0079 (3) |
O1 | 0.033 (1) | 0.058 (1) | 0.046 (1) | 0.008 (1) | 0.006 (1) | 0.014 (1) |
O2 | 0.056 (1) | 0.033 (1) | 0.062 (1) | −0.001 (1) | −0.020 (1) | 0.001 (1) |
N1 | 0.035 (1) | 0.032 (1) | 0.031 (1) | 0.001 (1) | −0.004 (1) | 0.001 (1) |
N2 | 0.037 (1) | 0.034 (1) | 0.035 (1) | 0.002 (1) | 0.005 (1) | −0.003 (1) |
C1 | 0.030 (1) | 0.030 (1) | 0.055 (2) | −0.001 (1) | 0.003 (1) | 0.001 (1) |
C2 | 0.042 (1) | 0.038 (1) | 0.069 (2) | −0.001 (1) | 0.016 (1) | 0.005 (1) |
C3 | 0.035 (1) | 0.044 (1) | 0.101 (3) | −0.005 (1) | 0.019 (1) | −0.012 (2) |
C4 | 0.030 (1) | 0.060 (2) | 0.102 (3) | 0.005 (1) | −0.006 (2) | −0.019 (2) |
C5 | 0.041 (1) | 0.050 (2) | 0.074 (2) | 0.006 (1) | −0.014 (1) | −0.011 (1) |
C6 | 0.030 (1) | 0.031 (1) | 0.051 (2) | 0.002 (1) | −0.005 (1) | −0.006 (1) |
C7 | 0.044 (1) | 0.030 (1) | 0.036 (1) | −0.001 (1) | −0.009 (1) | −0.002 (1) |
C8 | 0.049 (1) | 0.056 (2) | 0.032 (1) | 0.001 (1) | 0.001 (1) | 0.003 (1) |
C9 | 0.043 (1) | 0.029 (1) | 0.036 (1) | 0.002 (1) | 0.007 (1) | −0.002 (1) |
C10 | 0.062 (2) | 0.043 (1) | 0.042 (1) | −0.004 (1) | 0.019 (1) | −0.002 (1) |
C11 | 0.052 (2) | 0.051 (1) | 0.063 (2) | −0.007 (1) | 0.025 (1) | −0.004 (1) |
C12 | 0.037 (1) | 0.065 (2) | 0.064 (2) | 0.005 (1) | 0.012 (1) | −0.006 (2) |
C13 | 0.038 (1) | 0.052 (1) | 0.048 (2) | 0.008 (1) | 0.005 (1) | −0.002 (1) |
C14 | 0.086 (2) | 0.044 (2) | 0.090 (3) | −0.010 (1) | −0.043 (2) | −0.004 (2) |
Geometric parameters (Å, º) top
Fe1—Cl1 | 2.292 (1) | C9—C10 | 1.383 (3) |
Fe1—Cl2 | 2.349 (1) | C10—C11 | 1.383 (4) |
Fe1—O1 | 1.889 (2) | C11—C12 | 1.375 (4) |
Fe1—O2 | 2.206 (2) | C12—C13 | 1.364 (4) |
Fe1—N1 | 2.106 (2) | O2—H2O | 0.84 (1) |
Fe1—N2 | 2.163 (2) | C2—H2 | 0.93 |
O1—C1 | 1.343 (3) | C3—H3 | 0.93 |
O2—C14 | 1.413 (3) | C4—H4 | 0.93 |
N1—C7 | 1.283 (3) | C5—H5 | 0.93 |
N1—C8 | 1.468 (3) | C7—H7 | 0.93 |
N2—C9 | 1.338 (3) | C8—H8A | 0.97 |
N2—C13 | 1.348 (3) | C8—H8B | 0.97 |
C1—C2 | 1.389 (3) | C10—H10 | 0.93 |
C1—C6 | 1.403 (3) | C11—H11 | 0.93 |
C2—C3 | 1.398 (4) | C12—H12 | 0.93 |
C3—C4 | 1.378 (6) | C13—H13 | 0.93 |
C4—C5 | 1.361 (5) | C14—H14A | 0.96 |
C5—C6 | 1.420 (3) | C14—H14B | 0.96 |
C6—C7 | 1.433 (3) | C14—H14C | 0.96 |
C8—C9 | 1.499 (3) | ||
Cl1—Fe1—Cl2 | 97.41 (3) | C10—C9—C8 | 121.3 (2) |
Cl1—Fe1—O1 | 98.88 (5) | C9—C10—C11 | 118.6 (3) |
Cl1—Fe1—O2 | 82.99 (5) | C12—C11—C10 | 119.3 (2) |
Cl1—Fe1—N1 | 166.74 (5) | C13—C12—C11 | 118.9 (3) |
Cl1—Fe1—N2 | 95.79 (5) | N2—C13—C12 | 122.9 (3) |
Cl2—Fe1—O1 | 97.40 (6) | Fe1—O2—H2O | 109 (3) |
Cl2—Fe1—O2 | 171.42 (6) | C14—O2—H2O | 112 (2) |
Cl2—Fe1—N1 | 93.26 (5) | C1—C2—H2 | 120.2 |
Cl2—Fe1—N2 | 87.33 (5) | C3—C2—H2 | 120.2 |
O1—Fe1—O2 | 91.00 (8) | C4—C3—H3 | 119.6 |
O1—Fe1—N1 | 87.49 (7) | C2—C3—H3 | 119.6 |
O1—Fe1—N2 | 163.85 (8) | C5—C4—H4 | 120.0 |
O2—Fe1—N1 | 85.30 (7) | C3—C4—H4 | 120.0 |
O2—Fe1—N2 | 84.10 (7) | C4—C5—H5 | 119.5 |
N1—Fe1—N2 | 76.80 (7) | C6—C5—H5 | 119.5 |
C1—O1—Fe1 | 134.0 (2) | N1—C7—H7 | 117.0 |
C14—O2—Fe1 | 127.6 (2) | C6—C7—H7 | 117.0 |
C7—N1—C8 | 117.1 (2) | N1—C8—H8A | 109.4 |
C7—N1—Fe1 | 125.8 (2) | C9—C8—H8A | 109.4 |
C8—N1—Fe1 | 117.0 (1) | N1—C8—H8B | 109.4 |
C9—N2—C13 | 118.0 (2) | C9—C8—H8B | 109.4 |
C9—N2—Fe1 | 117.0 (2) | H8A—C8—H8B | 108.0 |
C13—N2—Fe1 | 124.4 (2) | C9—C10—H10 | 120.7 |
O1—C1—C2 | 118.4 (2) | C11—C10—H10 | 120.7 |
O1—C1—C6 | 121.7 (2) | C12—C11—H11 | 120.4 |
C2—C1—C6 | 120.0 (2) | C10—C11—H11 | 120.4 |
C1—C2—C3 | 119.7 (3) | C13—C12—H12 | 120.6 |
C4—C3—C2 | 120.8 (3) | C11—C12—H12 | 120.6 |
C5—C4—C3 | 119.9 (2) | N2—C13—H13 | 118.5 |
C4—C5—C6 | 121.1 (3) | C12—C13—H13 | 118.5 |
C1—C6—C5 | 118.5 (2) | O2—C14—H14A | 109.5 |
C1—C6—C7 | 124.00 (19) | O2—C14—H14B | 109.5 |
C5—C6—C7 | 117.5 (2) | H14A—C14—H14B | 109.5 |
N1—C7—C6 | 125.9 (2) | O2—C14—H14C | 109.5 |
N1—C8—C9 | 111.3 (2) | H14A—C14—H14C | 109.5 |
N2—C9—C10 | 122.3 (2) | H14B—C14—H14C | 109.5 |
N2—C9—C8 | 116.4 (2) | ||
N1—Fe1—O1—C1 | 12.1 (2) | O1—C1—C2—C3 | 177.4 (2) |
N2—Fe1—O1—C1 | 25.3 (4) | C6—C1—C2—C3 | −1.5 (3) |
O2—Fe1—O1—C1 | 97.3 (2) | C1—C2—C3—C4 | 1.0 (4) |
Cl1—Fe1—O1—C1 | −179.6 (2) | C2—C3—C4—C5 | 0.8 (4) |
Cl2—Fe1—O1—C1 | −80.9 (2) | C3—C4—C5—C6 | −1.9 (4) |
O1—Fe1—O2—C14 | −41.9 (3) | O1—C1—C6—C5 | −178.5 (2) |
N1—Fe1—O2—C14 | 45.5 (3) | C2—C1—C6—C5 | 0.4 (3) |
N2—Fe1—O2—C14 | 122.7 (3) | O1—C1—C6—C7 | 0.3 (3) |
Cl1—Fe1—O2—C14 | −140.7 (3) | C2—C1—C6—C7 | 179.2 (2) |
O1—Fe1—N1—C7 | −9.7 (2) | C4—C5—C6—C1 | 1.3 (3) |
N2—Fe1—N1—C7 | 174.0 (2) | C4—C5—C6—C7 | −177.6 (2) |
O2—Fe1—N1—C7 | −100.9 (2) | C8—N1—C7—C6 | −177.8 (2) |
Cl1—Fe1—N1—C7 | −128.9 (2) | Fe1—N1—C7—C6 | 5.9 (3) |
Cl2—Fe1—N1—C7 | 87.6 (2) | C1—C6—C7—N1 | 0.7 (3) |
O1—Fe1—N1—C8 | 174.0 (2) | C5—C6—C7—N1 | 179.5 (2) |
N2—Fe1—N1—C8 | −2.2 (2) | C7—N1—C8—C9 | −167.8 (2) |
O2—Fe1—N1—C8 | 82.8 (2) | Fe1—N1—C8—C9 | 8.8 (3) |
Cl1—Fe1—N1—C8 | 54.8 (3) | C13—N2—C9—C10 | 2.6 (3) |
Cl2—Fe1—N1—C8 | −88.7 (2) | Fe1—N2—C9—C10 | −168.9 (2) |
O1—Fe1—N2—C9 | −19.4 (3) | C13—N2—C9—C8 | −176.0 (2) |
N1—Fe1—N2—C9 | −5.7 (2) | Fe1—N2—C9—C8 | 12.5 (3) |
O2—Fe1—N2—C9 | −92.3 (2) | N1—C8—C9—N2 | −13.7 (3) |
Cl1—Fe1—N2—C9 | −174.6 (2) | N1—C8—C9—C10 | 167.6 (2) |
Cl2—Fe1—N2—C9 | 88.3 (2) | N2—C9—C10—C11 | −1.9 (3) |
O1—Fe1—N2—C13 | 169.7 (2) | C8—C9—C10—C11 | 176.8 (2) |
N1—Fe1—N2—C13 | −176.6 (2) | C9—C10—C11—C12 | −0.4 (4) |
O2—Fe1—N2—C13 | 96.8 (2) | C10—C11—C12—C13 | 1.8 (4) |
Cl1—Fe1—N2—C13 | 14.5 (2) | C9—N2—C13—C12 | −1.2 (4) |
Cl2—Fe1—N2—C13 | −82.7 (2) | Fe1—N2—C13—C12 | 169.6 (2) |
Fe1—O1—C1—C2 | 171.4 (2) | C11—C12—C13—N2 | −1.0 (4) |
Fe1—O1—C1—C6 | −9.7 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2O···Cl2i | 0.84 (1) | 2.51 (2) | 3.295 (2) | 157 (3) |
Symmetry code: (i) x, y+1, z. |