metal-organic compounds
In the title complex, [Fe(C18H17N2O3)Cl2], the FeIII species has a distorted trigonal–bipyramidal geometry, defined by two O atoms and one N atom from the tridentate hydrazone ligand and two Cl− anions. A hydrogen-bonded dimer is formed via two N—HCl intermolecular hydrogen bonds across a center of inversion.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804022755/hb6093sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804022755/hb6093Isup2.hkl |
CCDC reference: 252777
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.
Crystal data top
[Fe(C18H17N2O3)Cl2] | F(000) = 892 |
Mr = 436.09 | Dx = 1.533 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 17064 reflections |
a = 7.5958 (3) Å | θ = 3.1–27.5° |
b = 13.4330 (3) Å | µ = 1.10 mm−1 |
c = 18.5880 (4) Å | T = 293 K |
β = 94.973 (3)° | Prism, black |
V = 1889.48 (10) Å3 | 0.39 × 0.26 × 0.18 mm |
Z = 4 |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 4303 independent reflections |
Radiation source: fine-focus sealed tube | 3411 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
Detector resolution: 10 pixels mm-1 | θmax = 27.4°, θmin = 3.0° |
ω scans | h = −8→9 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −17→17 |
Tmin = 0.673, Tmax = 0.827 | l = −24→24 |
17967 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)] = 0.042 | Hydrogen site location: difmap (N-H) and geom (C-H) |
wR(F2) = 0.100 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0455P)2 + 0.877P] where P = (Fo2 + 2Fc2)/3 |
4303 reflections | (Δ/σ)max = 0.001 |
240 parameters | Δρmax = 0.37 e Å−3 |
1 restraint | Δρmin = −0.21 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Fe1 | 0.71549 (5) | 0.65743 (2) | 0.556481 (16) | 0.04250 (12) | |
Cl2 | 0.48747 (10) | 0.69533 (5) | 0.62004 (3) | 0.05641 (18) | |
Cl1 | 0.96420 (10) | 0.71821 (6) | 0.61083 (4) | 0.0684 (2) | |
O3 | 0.8747 (3) | 0.06932 (13) | 0.68408 (10) | 0.0658 (5) | |
O1 | 0.6655 (3) | 0.75805 (12) | 0.48459 (9) | 0.0554 (5) | |
O2 | 0.7355 (3) | 0.51826 (12) | 0.60023 (9) | 0.0604 (5) | |
N1 | 0.7393 (3) | 0.56395 (13) | 0.46933 (10) | 0.0437 (5) | |
N2 | 0.7662 (3) | 0.46468 (13) | 0.48980 (10) | 0.0469 (5) | |
H19 | 0.767 (4) | 0.4164 (16) | 0.4569 (12) | 0.070* | |
C12 | 0.7858 (3) | 0.34449 (16) | 0.58836 (12) | 0.0433 (5) | |
C5 | 0.6525 (3) | 0.86496 (16) | 0.38373 (12) | 0.0399 (5) | |
C7 | 0.6114 (4) | 0.97428 (19) | 0.28109 (14) | 0.0578 (7) | |
H7 | 0.6031 | 0.9834 | 0.2313 | 0.069* | |
C3 | 0.7228 (4) | 0.68394 (17) | 0.37535 (12) | 0.0454 (6) | |
H3 | 0.7328 | 0.6952 | 0.3265 | 0.054* | |
C4 | 0.6817 (3) | 0.76489 (16) | 0.41634 (12) | 0.0416 (5) | |
C15 | 0.8451 (4) | 0.15667 (17) | 0.64897 (14) | 0.0484 (6) | |
C10 | 0.6353 (4) | 0.94634 (17) | 0.42833 (13) | 0.0504 (6) | |
H10 | 0.6423 | 0.9376 | 0.4781 | 0.061* | |
C1 | 0.7958 (4) | 0.50882 (18) | 0.34653 (13) | 0.0539 (7) | |
H1A | 0.9085 | 0.4798 | 0.3617 | 0.081* | |
H1B | 0.8008 | 0.5393 | 0.3001 | 0.081* | |
H1C | 0.7069 | 0.4579 | 0.3435 | 0.081* | |
C14 | 0.8337 (4) | 0.16853 (17) | 0.57535 (14) | 0.0502 (6) | |
H14 | 0.8462 | 0.1137 | 0.5456 | 0.060* | |
C2 | 0.7510 (3) | 0.58610 (16) | 0.40036 (12) | 0.0417 (5) | |
C11 | 0.7597 (3) | 0.44562 (16) | 0.55938 (12) | 0.0435 (5) | |
C17 | 0.7977 (4) | 0.33112 (18) | 0.66272 (14) | 0.0596 (7) | |
H17 | 0.7857 | 0.3858 | 0.6926 | 0.071* | |
C9 | 0.6077 (4) | 1.04086 (19) | 0.39936 (14) | 0.0590 (7) | |
H9 | 0.5970 | 1.0952 | 0.4297 | 0.071* | |
C6 | 0.6391 (4) | 0.87999 (18) | 0.30961 (13) | 0.0527 (6) | |
H6 | 0.6488 | 0.8261 | 0.2788 | 0.063* | |
C8 | 0.5963 (4) | 1.05407 (18) | 0.32559 (14) | 0.0564 (7) | |
H8 | 0.5782 | 1.1174 | 0.3061 | 0.068* | |
C18 | 0.8997 (5) | −0.0183 (2) | 0.64249 (18) | 0.0703 (9) | |
H18A | 0.7947 | −0.0313 | 0.6114 | 0.105* | |
H18B | 0.9238 | −0.0738 | 0.6743 | 0.105* | |
H18C | 0.9976 | −0.0085 | 0.6138 | 0.105* | |
C16 | 0.8267 (5) | 0.2388 (2) | 0.69277 (14) | 0.0655 (8) | |
H16 | 0.8342 | 0.2313 | 0.7427 | 0.079* | |
C13 | 0.8036 (4) | 0.26184 (17) | 0.54525 (13) | 0.0498 (6) | |
H13 | 0.7952 | 0.2691 | 0.4953 | 0.060* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Fe1 | 0.0665 (2) | 0.03262 (17) | 0.02835 (16) | 0.00726 (15) | 0.00375 (14) | 0.00282 (12) |
Cl2 | 0.0757 (4) | 0.0472 (3) | 0.0481 (3) | 0.0102 (3) | 0.0153 (3) | 0.0056 (3) |
Cl1 | 0.0737 (5) | 0.0576 (4) | 0.0712 (5) | 0.0021 (3) | −0.0088 (4) | −0.0033 (3) |
O3 | 0.1039 (16) | 0.0398 (9) | 0.0545 (11) | 0.0118 (10) | 0.0116 (10) | 0.0170 (8) |
O1 | 0.0961 (14) | 0.0385 (8) | 0.0326 (8) | 0.0149 (9) | 0.0109 (9) | 0.0074 (7) |
O2 | 0.1114 (16) | 0.0350 (8) | 0.0356 (9) | 0.0157 (9) | 0.0110 (9) | 0.0042 (7) |
N1 | 0.0656 (13) | 0.0310 (9) | 0.0340 (10) | 0.0046 (9) | 0.0017 (9) | 0.0029 (7) |
N2 | 0.0787 (15) | 0.0289 (9) | 0.0331 (10) | 0.0067 (9) | 0.0052 (10) | 0.0029 (7) |
C12 | 0.0579 (14) | 0.0351 (11) | 0.0369 (11) | 0.0050 (10) | 0.0043 (10) | 0.0056 (9) |
C5 | 0.0493 (13) | 0.0360 (11) | 0.0345 (11) | 0.0030 (10) | 0.0041 (10) | 0.0068 (9) |
C7 | 0.093 (2) | 0.0453 (13) | 0.0348 (12) | −0.0001 (14) | 0.0023 (13) | 0.0111 (10) |
C3 | 0.0675 (16) | 0.0380 (11) | 0.0308 (11) | 0.0049 (11) | 0.0050 (11) | 0.0066 (9) |
C4 | 0.0518 (14) | 0.0397 (11) | 0.0329 (11) | 0.0025 (10) | 0.0021 (10) | 0.0058 (9) |
C15 | 0.0606 (15) | 0.0384 (12) | 0.0466 (13) | 0.0059 (11) | 0.0058 (11) | 0.0131 (10) |
C10 | 0.0748 (18) | 0.0423 (12) | 0.0350 (12) | 0.0092 (12) | 0.0091 (12) | 0.0058 (10) |
C1 | 0.087 (2) | 0.0413 (12) | 0.0343 (12) | 0.0051 (13) | 0.0103 (12) | 0.0000 (10) |
C14 | 0.0709 (17) | 0.0360 (12) | 0.0434 (13) | 0.0059 (11) | 0.0031 (12) | 0.0006 (10) |
C2 | 0.0563 (14) | 0.0368 (11) | 0.0320 (11) | 0.0025 (10) | 0.0035 (10) | 0.0009 (9) |
C11 | 0.0583 (15) | 0.0358 (11) | 0.0364 (12) | 0.0043 (10) | 0.0032 (11) | 0.0036 (9) |
C17 | 0.100 (2) | 0.0404 (13) | 0.0395 (13) | 0.0132 (14) | 0.0124 (14) | 0.0046 (10) |
C9 | 0.093 (2) | 0.0380 (12) | 0.0470 (14) | 0.0123 (13) | 0.0140 (14) | 0.0019 (11) |
C6 | 0.0843 (19) | 0.0380 (12) | 0.0353 (12) | 0.0013 (12) | 0.0031 (12) | 0.0030 (9) |
C8 | 0.084 (2) | 0.0356 (12) | 0.0498 (15) | 0.0069 (12) | 0.0068 (14) | 0.0115 (11) |
C18 | 0.097 (2) | 0.0406 (14) | 0.074 (2) | 0.0133 (15) | 0.0125 (18) | 0.0121 (13) |
C16 | 0.113 (2) | 0.0503 (15) | 0.0346 (13) | 0.0140 (16) | 0.0141 (14) | 0.0110 (11) |
C13 | 0.0753 (17) | 0.0397 (12) | 0.0335 (12) | 0.0051 (12) | −0.0003 (11) | 0.0045 (9) |
Geometric parameters (Å, º) top
Fe1—Cl1 | 2.2192 (8) | C6—H6 | 0.9300 |
Fe1—Cl2 | 2.2382 (7) | C7—C8 | 1.365 (4) |
Fe1—N1 | 2.070 (2) | C7—C6 | 1.382 (3) |
Fe1—O1 | 1.916 (2) | C7—H7 | 0.9300 |
Fe1—O2 | 2.039 (2) | C8—H8 | 0.9300 |
N1—C2 | 1.326 (3) | C9—C8 | 1.378 (4) |
O1—C4 | 1.289 (3) | C9—H9 | 0.9300 |
O2—C11 | 1.259 (3) | C10—C9 | 1.388 (3) |
C3—C4 | 1.379 (3) | C10—H10 | 0.9300 |
N1—N2 | 1.397 (2) | C12—C13 | 1.383 (3) |
N2—C11 | 1.324 (3) | C12—C17 | 1.389 (3) |
N2—H19 | 0.89 (2) | C12—C11 | 1.468 (3) |
O3—C15 | 1.352 (3) | C14—C13 | 1.384 (3) |
O3—C18 | 1.430 (3) | C14—H14 | 0.9300 |
C1—C2 | 1.501 (3) | C15—C14 | 1.373 (3) |
C1—H1A | 0.9600 | C15—C16 | 1.386 (4) |
C1—H1B | 0.9600 | C17—C16 | 1.370 (3) |
C1—H1C | 0.9600 | C17—H17 | 0.9300 |
C3—C2 | 1.404 (3) | C18—H18A | 0.9600 |
C3—H3 | 0.9300 | C18—H18B | 0.9600 |
C5—C10 | 1.385 (3) | C18—H18C | 0.9600 |
C5—C6 | 1.387 (3) | C16—H16 | 0.9300 |
C5—C4 | 1.483 (3) | C13—H13 | 0.9300 |
Cl1—Fe1—Cl2 | 110.07 (3) | C7—C6—C5 | 120.7 (2) |
N1—Fe1—Cl1 | 116.79 (6) | C7—C6—H6 | 119.7 |
N1—Fe1—Cl2 | 132.47 (6) | C7—C8—C9 | 120.0 (2) |
O1—Fe1—Cl1 | 99.64 (7) | C7—C8—H8 | 120.0 |
O1—Fe1—Cl2 | 95.28 (6) | C8—C7—C6 | 120.3 (2) |
O1—Fe1—N1 | 84.70 (7) | C8—C7—H7 | 119.8 |
O1—Fe1—O2 | 158.22 (8) | C8—C9—C10 | 119.9 (2) |
O2—Fe1—Cl1 | 97.16 (6) | C8—C9—H9 | 120.1 |
O2—Fe1—Cl2 | 91.86 (6) | C9—C8—H8 | 120.0 |
O2—Fe1—N1 | 75.37 (7) | C9—C10—H10 | 119.7 |
N1—N2—H19 | 121 (2) | C10—C5—C4 | 119.3 (2) |
N1—C2—C1 | 121.8 (2) | C10—C5—C6 | 118.5 (2) |
N1—C2—C3 | 120.6 (2) | C10—C9—H9 | 120.1 |
N2—N1—Fe1 | 112.74 (13) | C11—N2—N1 | 115.72 (19) |
N2—C11—C12 | 121.5 (2) | C11—N2—H19 | 122 (2) |
O1—C4—C3 | 122.2 (2) | C11—O2—Fe1 | 118.66 (15) |
O1—C4—C5 | 116.3 (2) | C12—C13—C14 | 120.9 (2) |
O2—C11—N2 | 117.3 (2) | C12—C13—H13 | 119.5 |
O2—C11—C12 | 121.2 (2) | C12—C17—H17 | 119.4 |
O3—C15—C14 | 125.1 (2) | C13—C12—C17 | 118.1 (2) |
O3—C15—C16 | 115.4 (2) | C13—C12—C11 | 123.2 (2) |
O3—C18—H18C | 109.5 | C13—C14—H14 | 119.9 |
O3—C18—H18A | 109.5 | C14—C13—H13 | 119.5 |
O3—C18—H18B | 109.5 | C14—C15—C16 | 119.5 (2) |
C2—N1—Fe1 | 129.65 (15) | C15—O3—C18 | 118.5 (2) |
C2—N1—N2 | 117.19 (19) | C15—C14—C13 | 120.1 (2) |
C2—C1—H1A | 109.5 | C15—C14—H14 | 119.9 |
C2—C1—H1B | 109.5 | C15—C16—H16 | 119.9 |
C2—C1—H1C | 109.5 | C16—C17—C12 | 121.1 (2) |
C2—C3—H3 | 116.9 | C16—C17—H17 | 119.4 |
C3—C2—C1 | 117.6 (2) | C17—C12—C11 | 118.7 (2) |
C3—C4—C5 | 121.5 (2) | C17—C16—C15 | 120.1 (2) |
C4—O1—Fe1 | 134.99 (15) | C17—C16—H16 | 119.9 |
C4—C3—C2 | 126.2 (2) | H1A—C1—H1B | 109.5 |
C4—C3—H3 | 116.9 | H1A—C1—H1C | 109.5 |
C5—C6—H6 | 119.7 | H1B—C1—H1C | 109.5 |
C5—C10—C9 | 120.6 (2) | H18A—C18—H18B | 109.5 |
C5—C10—H10 | 119.7 | H18A—C18—H18C | 109.5 |
C6—C5—C4 | 122.2 (2) | H18B—C18—H18C | 109.5 |
C6—C7—H7 | 119.8 | ||
Fe1—N1—N2—C11 | 4.5 (3) | C2—C3—C4—O1 | 0.3 (4) |
Fe1—O1—C4—C3 | 10.2 (4) | C2—C3—C4—C5 | −179.2 (2) |
Fe1—O1—C4—C5 | −170.28 (18) | C4—C3—C2—N1 | −0.1 (4) |
Fe1—N1—C2—C3 | −9.1 (4) | C4—C3—C2—C1 | −179.5 (3) |
Fe1—N1—C2—C1 | 170.31 (19) | C4—C5—C6—C7 | 179.9 (3) |
Fe1—O2—C11—N2 | −1.6 (3) | C4—C5—C10—C9 | −180.0 (3) |
Fe1—O2—C11—C12 | 176.29 (18) | C5—C10—C9—C8 | 0.4 (5) |
Cl1—Fe1—N1—N2 | 86.83 (17) | C6—C5—C4—O1 | −169.9 (2) |
Cl1—Fe1—N1—C2 | −85.4 (2) | C6—C5—C10—C9 | −0.9 (4) |
Cl1—Fe1—O1—C4 | 102.7 (2) | C6—C5—C4—C3 | 9.6 (4) |
Cl1—Fe1—O2—C11 | −112.7 (2) | C6—C7—C8—C9 | −0.3 (5) |
Cl2—Fe1—N1—N2 | −82.72 (17) | C8—C7—C6—C5 | −0.2 (5) |
Cl2—Fe1—N1—C2 | 105.1 (2) | C10—C5—C4—O1 | 9.1 (3) |
Cl2—Fe1—O1—C4 | −145.9 (2) | C10—C5—C4—C3 | −171.3 (2) |
Cl2—Fe1—O2—C11 | 136.8 (2) | C10—C5—C6—C7 | 0.8 (4) |
N1—Fe1—O1—C4 | −13.6 (3) | C10—C9—C8—C7 | 0.2 (5) |
N1—Fe1—O2—C11 | 3.1 (2) | C11—C12—C13—C14 | 177.9 (3) |
N1—N2—C11—O2 | −2.0 (4) | C11—C12—C17—C16 | −178.2 (3) |
N1—N2—C11—C12 | −179.9 (2) | C12—C17—C16—C15 | 0.1 (5) |
N2—N1—C2—C3 | 179.0 (2) | C13—C12—C11—N2 | −5.7 (4) |
N2—N1—C2—C1 | −1.6 (4) | C13—C12—C11—O2 | 176.5 (3) |
O1—Fe1—N1—N2 | −175.03 (18) | C13—C12—C17—C16 | 0.2 (5) |
O1—Fe1—N1—C2 | 12.8 (2) | C14—C15—C16—C17 | −0.1 (5) |
O1—Fe1—O2—C11 | 27.5 (4) | C15—C14—C13—C12 | 0.5 (4) |
O2—Fe1—N1—N2 | −3.89 (16) | C16—C15—C14—C13 | −0.2 (4) |
O2—Fe1—N1—C2 | −176.1 (2) | C17—C12—C11—N2 | 172.7 (3) |
O2—Fe1—O1—C4 | −37.3 (4) | C17—C12—C11—O2 | −5.1 (4) |
O3—C15—C14—C13 | −179.7 (3) | C17—C12—C13—C14 | −0.5 (4) |
O3—C15—C16—C17 | 179.5 (3) | C18—O3—C15—C14 | 1.2 (4) |
C2—N1—N2—C11 | 177.8 (2) | C18—O3—C15—C16 | −178.3 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H19···Cl2i | 0.89 (2) | 2.75 (2) | 3.438 (2) | 135 (2) |
Symmetry code: (i) −x+1, −y+1, −z+1. |