The main molecule of the title compound, [Fe2(C15H19ClN3O)2O](CF3O3S)2·2C2H3N, is located on a crystallographic inversion centre and displays disorder in the coordinated methoxyethyl group. The counter-ion and the cocrystallized solvent molecule are also disordered over multiple positions. The five-membered chelate rings involving the pyridine N atoms are in an envelope conformation. The chelate ring involving the ether O atom is in a half-chair conformation in both disorder components.
Supporting information
CCDC reference: 274405
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.009 Å
- Disorder in main residue
- R factor = 0.064
- wR factor = 0.184
- Data-to-parameter ratio = 16.4
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT432_ALERT_2_A Short Inter X...Y Contact C43A .. O13C .. 2.59 Ang.
| Author Response:
The contact is between two disorder components. The occupancy of C43A
is 0.62, that of O13C is 0.22. It is therefore statistically possible
to avoid the occurence of this short contact in all unit cells of the
crystal.
|
Alert level B
RINTA01_ALERT_3_B The value of Rint is greater than 0.15
Rint given 0.167
PLAT020_ALERT_3_B The value of Rint is greater than 0.10 ......... 0.17
PLAT431_ALERT_2_B Short Inter HL..A Contact F12C .. F13C .. 2.55 Ang.
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT202_ALERT_3_C Isotropic non-H Atoms in Anion/Solvent ......... 3
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.82 Ratio
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C23
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C30
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C1A
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C1B
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C1C
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C42A
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C42B
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.32
PLAT301_ALERT_3_C Main Residue Disorder ......................... 4.00 Perc.
PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 37.00 Perc.
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9
PLAT432_ALERT_2_C Short Inter X...Y Contact C22 .. O12A .. 3.01 Ang.
| Author Response:
The contact is between two disorder components. The occupancy of C43A
is 0.62, that of O13C is 0.22. It is therefore statistically possible
to avoid the occurence of this short contact in all unit cells of the
crystal.
|
1 ALERT level A = In general: serious problem
3 ALERT level B = Potentially serious problem
15 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
7 ALERT type 2 Indicator that the structure model may be wrong or deficient
5 ALERT type 3 Indicator that the structure quality may be low
6 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.
µ-Oxo-bis{chloro[
N-(2-methoxyethyl)-
N,
N-bis(pyridin-2-ylmethyl)amine-
κ4-N,
N',
N'',
O]iron(III)}
bis(trifluoromethanesulfonate) acetonitrile disolvate
top
Crystal data top
[Fe2(C15H19ClN3O)2O](CF3O3S)2·2C2H3N | Z = 1 |
Mr = 1093.53 | F(000) = 560 |
Triclinic, P1 | Quoted _cell_measurement_* data items refer to the initial cell
determination. The cell parameters as reported in _cell_* are based
on the complete data set. |
Hall symbol: -P 1 | Dx = 1.582 Mg m−3 |
a = 8.6773 (10) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.585 (2) Å | Cell parameters from 244 reflections |
c = 12.068 (2) Å | θ = 2.0–25.0° |
α = 77.137 (14)° | µ = 0.92 mm−1 |
β = 79.072 (14)° | T = 150 K |
γ = 79.279 (14)° | Block, dark orange |
V = 1148.1 (3) Å3 | 0.20 × 0.10 × 0.10 mm |
Data collection top
Nonius KappaCCD area-detector diffractometer | 3784 reflections with I > 2σ(I) |
Radiation source: Rotating Anode | Rint = 0.167 |
Graphite monochromator | θmax = 27.0°, θmin = 1.8° |
Detector resolution: 18.4 pixels mm-1 | h = −11→11 |
φ scans and ω scans with κ offset | k = −14→14 |
36193 measured reflections | l = −15→15 |
5000 independent 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)] = 0.064 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.185 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0791P)2 + 1.96P] where P = (Fo2 + 2Fc2)/3 |
5000 reflections | (Δ/σ)max < 0.001 |
304 parameters | Δρmax = 1.38 e Å−3 |
230 restraints | Δρmin = −0.88 e Å−3 |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su's are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user
for potential systematic errors. Weighted R-factors wR and all
goodnesses of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The observed criterion of F2 > 2σ(F2)
is used only for calculating -R-factor-obs 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Fe1 | 0.37815 (6) | 0.02391 (5) | 0.63165 (5) | 0.0326 (2) | |
Cl1 | 0.21148 (12) | −0.11418 (10) | 0.66332 (10) | 0.0428 (3) | |
O1 | 0.50000 | 0.00000 | 0.50000 | 0.0374 (13) | |
O2 | 0.2644 (5) | 0.0669 (3) | 0.8094 (3) | 0.0562 (11) | |
N1 | 0.2353 (4) | 0.1794 (3) | 0.5526 (3) | 0.0331 (10) | |
N2 | 0.5626 (5) | −0.0668 (4) | 0.7282 (4) | 0.0522 (14) | |
N3 | 0.4914 (4) | 0.1709 (4) | 0.6487 (3) | 0.0455 (14) | |
C10 | 0.4731 (5) | 0.2633 (5) | 0.5438 (4) | 0.0474 (16) | |
C11 | 0.3084 (5) | 0.2766 (4) | 0.5159 (4) | 0.0379 (12) | |
C12 | 0.2383 (6) | 0.3806 (4) | 0.4525 (4) | 0.0478 (16) | |
C13 | 0.0886 (7) | 0.3852 (4) | 0.4265 (4) | 0.0499 (16) | |
C14 | 0.0134 (6) | 0.2848 (4) | 0.4652 (4) | 0.0479 (17) | |
C15 | 0.0894 (5) | 0.1837 (4) | 0.5273 (4) | 0.0399 (14) | |
C20 | 0.6612 (6) | 0.1207 (6) | 0.6547 (5) | 0.062 (2) | |
C21 | 0.6766 (5) | −0.0041 (7) | 0.7271 (4) | 0.060 (2) | |
C22 | 0.8069 (6) | −0.0505 (9) | 0.7834 (5) | 0.087 (3) | |
C23 | 0.8190 (8) | −0.1655 (10) | 0.8424 (6) | 0.107 (4) | |
C24 | 0.7046 (8) | −0.2313 (8) | 0.8433 (6) | 0.091 (3) | |
C25 | 0.5746 (7) | −0.1810 (6) | 0.7860 (5) | 0.0656 (19) | |
C30 | 0.4113 (7) | 0.2256 (6) | 0.7491 (5) | 0.072 (2) | |
C31A | 0.3633 (8) | 0.1406 (6) | 0.8485 (6) | 0.052 (2) | 0.796 (10) |
C32 | 0.2118 (6) | −0.0179 (5) | 0.9083 (4) | 0.0491 (17) | |
C31B | 0.249 (3) | 0.186 (2) | 0.804 (2) | 0.0520* | 0.204 (10) |
S1A | 0.0681 (4) | 0.7195 (3) | 0.1578 (3) | 0.0424 (5)* | 0.406 (3) |
S1B | 0.1084 (6) | 0.7000 (5) | 0.1409 (4) | 0.0424 (5)* | 0.317 (3) |
S1C | 0.1557 (6) | 0.6540 (5) | 0.1225 (4) | 0.0424 (5)* | 0.277 (2) |
F11A | 0.3652 (11) | 0.6811 (9) | 0.0675 (8) | 0.0676 (10)* | 0.406 (3) |
F11B | 0.3711 (13) | 0.6478 (11) | 0.0193 (10) | 0.0676 (10)* | 0.317 (3) |
F11C | 0.4225 (14) | 0.7347 (10) | 0.0638 (10) | 0.0676 (10)* | 0.277 (2) |
F12A | 0.2442 (10) | 0.5173 (7) | 0.1392 (8) | 0.0676 (10)* | 0.406 (3) |
F12B | 0.2392 (13) | 0.5039 (9) | 0.0857 (10) | 0.0676 (10)* | 0.317 (3) |
F12C | 0.3896 (14) | 0.6040 (11) | −0.0334 (9) | 0.0676 (10)* | 0.277 (2) |
F13A | 0.3107 (10) | 0.6197 (8) | 0.2566 (7) | 0.0676 (10)* | 0.406 (3) |
F13B | 0.3541 (13) | 0.5658 (10) | 0.2048 (9) | 0.0676 (10)* | 0.317 (3) |
F13C | 0.4343 (14) | 0.5482 (10) | 0.1434 (10) | 0.0676 (10)* | 0.277 (2) |
O11A | 0.0328 (15) | 0.7324 (14) | 0.0440 (9) | 0.0504 (8)* | 0.406 (3) |
O11B | 0.0122 (18) | 0.7247 (17) | 0.0543 (12) | 0.0504 (8)* | 0.317 (3) |
O11C | 0.0860 (16) | 0.7531 (11) | 0.0369 (10) | 0.0504 (8)* | 0.277 (2) |
O12A | 0.0895 (11) | 0.8312 (7) | 0.1769 (8) | 0.0504 (8)* | 0.406 (3) |
O12B | 0.1617 (14) | 0.8078 (9) | 0.1602 (10) | 0.0504 (8)* | 0.317 (3) |
O12C | 0.1420 (14) | 0.6816 (11) | 0.2359 (9) | 0.0504 (8)* | 0.277 (2) |
O13A | −0.0326 (10) | 0.6617 (9) | 0.2462 (8) | 0.0504 (8)* | 0.406 (3) |
O13B | 0.0126 (13) | 0.6438 (11) | 0.2499 (10) | 0.0504 (8)* | 0.317 (3) |
O13C | 0.1006 (14) | 0.5460 (10) | 0.1245 (10) | 0.0504 (8)* | 0.277 (2) |
C1A | 0.2616 (8) | 0.6313 (6) | 0.1619 (6) | 0.0100 (10)* | 0.406 (3) |
C1B | 0.2757 (10) | 0.6076 (8) | 0.1203 (8) | 0.0100 (10)* | 0.317 (3) |
C1C | 0.3633 (11) | 0.6350 (9) | 0.0679 (9) | 0.0100 (10)* | 0.277 (2) |
N41A | 0.6537 (14) | 0.4641 (11) | 0.3435 (9) | 0.065 (3)* | 0.668 (12) |
C42A | 0.7418 (11) | 0.4465 (8) | 0.2769 (8) | 0.047 (2)* | 0.668 (12) |
C43A | 0.8625 (12) | 0.4277 (9) | 0.1746 (8) | 0.068 (3)* | 0.668 (12) |
N41B | 0.675 (3) | 0.462 (2) | 0.366 (2) | 0.0650* | 0.332 (12) |
C42B | 0.712 (2) | 0.4622 (17) | 0.2477 (17) | 0.0470* | 0.332 (12) |
C43B | 0.758 (2) | 0.4476 (18) | 0.1342 (16) | 0.0680* | 0.332 (12) |
H10A | 0.55190 | 0.24010 | 0.47860 | 0.0570* | |
H12 | 0.29230 | 0.44830 | 0.42690 | 0.0570* | |
H13 | 0.03800 | 0.45600 | 0.38300 | 0.0600* | |
H10B | 0.49280 | 0.34070 | 0.55580 | 0.0570* | |
H15 | 0.03790 | 0.11490 | 0.55330 | 0.0480* | |
H20A | 0.70960 | 0.17310 | 0.68820 | 0.0740* | |
H20B | 0.71910 | 0.11820 | 0.57600 | 0.0740* | |
H22 | 0.88600 | −0.00280 | 0.78070 | 0.1050* | |
H23 | 0.90620 | −0.19930 | 0.88240 | 0.1290* | |
H24 | 0.71260 | −0.31220 | 0.88310 | 0.1090* | |
H25 | 0.49470 | −0.22770 | 0.78780 | 0.0780* | |
H30A | 0.48440 | 0.27180 | 0.76820 | 0.0870* | 0.796 (10) |
H30B | 0.31660 | 0.28250 | 0.72740 | 0.0870* | 0.796 (10) |
H31A | 0.29970 | 0.18140 | 0.90980 | 0.0620* | 0.796 (10) |
H31B | 0.45690 | 0.08910 | 0.87830 | 0.0620* | 0.796 (10) |
H32A | 0.30320 | −0.06170 | 0.94450 | 0.0740* | |
H32B | 0.15870 | −0.07440 | 0.88520 | 0.0740* | |
H32C | 0.13720 | 0.02410 | 0.96330 | 0.0740* | |
H14 | −0.08980 | 0.28600 | 0.44880 | 0.0570* | |
H30C | 0.39570 | 0.31380 | 0.72430 | 0.0870* | 0.204 (10) |
H30D | 0.48180 | 0.20460 | 0.80840 | 0.0870* | 0.204 (10) |
H31C | 0.21750 | 0.20470 | 0.88150 | 0.0620* | 0.204 (10) |
H31D | 0.16720 | 0.22860 | 0.75600 | 0.0620* | 0.204 (10) |
H43A | 0.85150 | 0.49870 | 0.11310 | 0.1010* | 0.668 (12) |
H43B | 0.84640 | 0.35770 | 0.14770 | 0.1010* | 0.668 (12) |
H43C | 0.96900 | 0.41450 | 0.19550 | 0.1010* | 0.668 (12) |
H43D | 0.86990 | 0.45670 | 0.10990 | 0.1010* | 0.332 (12) |
H43E | 0.69300 | 0.50820 | 0.08470 | 0.1010* | 0.332 (12) |
H43F | 0.74290 | 0.36750 | 0.12810 | 0.1010* | 0.332 (12) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Fe1 | 0.0193 (3) | 0.0420 (4) | 0.0406 (4) | −0.0029 (2) | −0.0015 (2) | −0.0206 (3) |
Cl1 | 0.0307 (5) | 0.0394 (6) | 0.0593 (7) | −0.0086 (4) | 0.0035 (5) | −0.0180 (5) |
O1 | 0.0196 (18) | 0.054 (3) | 0.046 (2) | −0.0053 (17) | 0.0005 (16) | −0.030 (2) |
O2 | 0.070 (2) | 0.0389 (18) | 0.052 (2) | −0.0120 (17) | 0.0236 (18) | −0.0176 (15) |
N1 | 0.0230 (16) | 0.0366 (18) | 0.043 (2) | −0.0108 (14) | 0.0030 (14) | −0.0162 (15) |
N2 | 0.031 (2) | 0.079 (3) | 0.054 (2) | 0.013 (2) | −0.0138 (18) | −0.040 (2) |
N3 | 0.0300 (19) | 0.066 (3) | 0.053 (2) | −0.0185 (18) | 0.0039 (16) | −0.037 (2) |
C10 | 0.033 (2) | 0.055 (3) | 0.063 (3) | −0.023 (2) | 0.011 (2) | −0.032 (2) |
C11 | 0.036 (2) | 0.039 (2) | 0.043 (2) | −0.0148 (19) | 0.0118 (18) | −0.0243 (19) |
C12 | 0.052 (3) | 0.038 (2) | 0.052 (3) | −0.016 (2) | 0.014 (2) | −0.017 (2) |
C13 | 0.062 (3) | 0.037 (2) | 0.048 (3) | −0.003 (2) | −0.002 (2) | −0.012 (2) |
C14 | 0.040 (3) | 0.046 (3) | 0.060 (3) | −0.006 (2) | −0.011 (2) | −0.013 (2) |
C15 | 0.029 (2) | 0.037 (2) | 0.055 (3) | −0.0070 (18) | −0.0044 (19) | −0.012 (2) |
C20 | 0.028 (2) | 0.118 (5) | 0.057 (3) | −0.026 (3) | −0.004 (2) | −0.043 (3) |
C21 | 0.025 (2) | 0.120 (5) | 0.044 (3) | −0.001 (3) | −0.006 (2) | −0.040 (3) |
C22 | 0.029 (3) | 0.192 (9) | 0.043 (3) | −0.007 (4) | −0.006 (2) | −0.035 (4) |
C23 | 0.032 (3) | 0.216 (11) | 0.050 (4) | 0.020 (5) | −0.006 (3) | −0.012 (5) |
C24 | 0.059 (4) | 0.135 (7) | 0.054 (4) | 0.040 (4) | −0.011 (3) | −0.012 (4) |
C25 | 0.052 (3) | 0.082 (4) | 0.058 (3) | 0.024 (3) | −0.014 (3) | −0.027 (3) |
C30 | 0.060 (3) | 0.101 (5) | 0.075 (4) | −0.040 (3) | 0.025 (3) | −0.066 (4) |
C31A | 0.056 (4) | 0.059 (4) | 0.050 (4) | −0.020 (3) | 0.007 (3) | −0.034 (3) |
C32 | 0.047 (3) | 0.048 (3) | 0.048 (3) | −0.010 (2) | 0.009 (2) | −0.012 (2) |
Geometric parameters (Å, º) top
Fe1—Cl1 | 2.2751 (13) | C12—C13 | 1.382 (8) |
Fe1—O1 | 1.7801 (7) | C13—C14 | 1.386 (7) |
Fe1—O2 | 2.305 (4) | C14—C15 | 1.370 (7) |
Fe1—N1 | 2.132 (4) | C20—C21 | 1.511 (10) |
Fe1—N2 | 2.135 (5) | C21—C22 | 1.390 (8) |
Fe1—N3 | 2.183 (4) | C22—C23 | 1.359 (14) |
S1A—O12A | 1.414 (9) | C23—C24 | 1.357 (12) |
S1A—O13A | 1.377 (10) | C24—C25 | 1.401 (10) |
S1A—C1A | 1.799 (8) | C30—C31A | 1.421 (9) |
S1A—O11A | 1.433 (11) | C30—C31B | 1.54 (3) |
S1B—O11B | 1.407 (16) | C10—H10B | 0.9900 |
S1B—O13B | 1.500 (13) | C10—H10A | 0.9900 |
S1B—C1B | 1.649 (11) | C12—H12 | 0.9500 |
S1B—O12B | 1.488 (12) | C13—H13 | 0.9500 |
S1C—O12C | 1.452 (12) | C14—H14 | 0.9500 |
S1C—O13C | 1.414 (13) | C15—H15 | 0.9500 |
S1C—C1C | 1.787 (11) | C20—H20A | 0.9900 |
S1C—O11C | 1.484 (14) | C20—H20B | 0.9900 |
F11A—C1A | 1.397 (12) | C22—H22 | 0.9500 |
F11B—C1B | 1.377 (15) | C23—H23 | 0.9500 |
F11C—C1C | 1.336 (16) | C24—H24 | 0.9500 |
F12A—C1A | 1.447 (11) | C25—H25 | 0.9500 |
F12B—C1B | 1.461 (14) | C30—H30C | 0.9900 |
F12C—C1C | 1.317 (15) | C30—H30A | 0.9900 |
F13A—C1A | 1.265 (11) | C30—H30B | 0.9900 |
F13B—C1B | 1.288 (14) | C30—H30D | 0.9900 |
F13C—C1C | 1.340 (16) | C31A—H31B | 0.9900 |
O2—C31B | 1.35 (2) | C31A—H31A | 0.9900 |
O2—C32 | 1.427 (6) | C31B—H31D | 0.9900 |
O2—C31A | 1.515 (8) | C31B—H31C | 0.9800 |
N1—C11 | 1.343 (6) | C32—H32C | 0.9800 |
N1—C15 | 1.347 (6) | C32—H32B | 0.9800 |
N2—C25 | 1.347 (8) | C32—H32A | 0.9800 |
N2—C21 | 1.328 (7) | C42A—C43A | 1.488 (14) |
N3—C30 | 1.487 (7) | C42B—C43B | 1.39 (3) |
N3—C10 | 1.478 (6) | C43A—H43A | 0.9800 |
N3—C20 | 1.489 (7) | C43A—H43B | 0.9800 |
N41A—C42A | 1.027 (15) | C43A—H43C | 0.9800 |
N41B—C42B | 1.40 (3) | C43B—H43D | 0.9800 |
C10—C11 | 1.502 (6) | C43B—H43E | 0.9800 |
C11—C12 | 1.379 (7) | C43B—H43F | 0.9800 |
| | | |
Fe1···H10Ai | 3.5100 | N3···O1 | 2.936 (4) |
Cl1···O1 | 3.1785 (12) | N3···C31B | 2.55 (3) |
Cl1···O2 | 3.167 (4) | N3···N1 | 2.672 (5) |
Cl1···N1 | 3.396 (4) | N3···C31A | 2.434 (8) |
Cl1···N2 | 3.452 (5) | N3···C21 | 2.470 (8) |
Cl1···C15 | 3.536 (5) | N41A···C10 | 3.336 (13) |
Cl1···C22ii | 3.543 (6) | N41B···C10 | 3.29 (2) |
Cl1···C25 | 3.615 (6) | N41B···C12vi | 3.41 (2) |
Cl1···C32 | 3.385 (5) | N1···H30B | 2.8900 |
Cl1···H15 | 2.9600 | N1···H31D | 2.5800 |
Cl1···H22ii | 3.1000 | N2···H31B | 2.7600 |
Cl1···H25 | 3.0600 | N41A···H10A | 2.9300 |
Cl1···H32B | 2.7600 | N41A···H10Bvi | 2.7900 |
Cl1···H10Ai | 2.8200 | N41A···H30Cvi | 2.5000 |
Cl1···H14iii | 3.0700 | N41A···H10B | 2.8800 |
Cl1···H20Bi | 2.8500 | N41B···H10A | 2.9200 |
S1A···O2iv | 3.457 (5) | N41B···H14ix | 2.7600 |
F11A···O12A | 2.961 (14) | N41B···H10B | 2.7800 |
F11A···O11A | 2.890 (17) | N41B···H10Bvi | 2.7300 |
F11B···O11B | 3.05 (2) | C1C···F12Cvii | 3.225 (16) |
F11B···O12B | 2.934 (17) | C10···N41B | 3.29 (2) |
F11C···C25v | 3.358 (13) | C10···N41A | 3.336 (13) |
F11C···C30vi | 3.055 (13) | C11···C31B | 3.37 (2) |
F11C···C24v | 3.264 (14) | C12···F13B | 3.370 (12) |
F11C···O12C | 2.948 (17) | C12···N41Bvi | 3.41 (2) |
F11C···O11C | 2.962 (19) | C12···F13A | 3.290 (10) |
F12A···C24i | 3.224 (12) | C13···C13iv | 3.483 (7) |
F12A···O11A | 2.953 (17) | C13···O13B | 3.303 (13) |
F12A···O13A | 2.920 (13) | C14···C42Aii | 3.567 (11) |
F12B···C24i | 3.054 (14) | C20···O12Bvi | 3.261 (13) |
F12B···C43Avii | 3.310 (15) | C21···C31A | 3.199 (9) |
F12B···O13B | 3.031 (16) | C22···O12Bvi | 3.107 (15) |
F12B···O11B | 2.92 (2) | C22···O12Avi | 3.008 (13) |
F12C···O11C | 2.959 (18) | C22···Cl1ix | 3.543 (6) |
F12C···C1Cvii | 3.225 (16) | C23···O11Bx | 3.217 (17) |
F12C···F12Cvii | 2.851 (18) | C23···O11Ax | 3.221 (14) |
F12C···C25v | 3.358 (13) | C24···F11Cxi | 3.264 (14) |
F12C···C43Avii | 3.133 (16) | C24···F12Bi | 3.054 (14) |
F12C···O13C | 2.935 (17) | C24···F12Ai | 3.224 (12) |
F12C···F13Cvii | 2.545 (17) | C25···F11Cxi | 3.358 (13) |
F13A···O13A | 2.950 (13) | C25···C32 | 3.595 (8) |
F13A···C30vi | 3.245 (11) | C25···F12Cxi | 3.358 (13) |
F13A···C12 | 3.290 (10) | C30···F11Cvi | 3.055 (14) |
F13A···O12A | 2.918 (13) | C30···O13Aiv | 3.297 (11) |
F13B···O12B | 2.977 (16) | C30···C42Bvi | 3.58 (2) |
F13B···O13B | 2.916 (17) | C30···F13Avi | 3.245 (11) |
F13B···C12 | 3.370 (12) | C31A···C21 | 3.199 (9) |
F13C···F12Cvii | 2.545 (17) | C31B···C11 | 3.37 (2) |
F13C···C42A | 3.274 (16) | C32···O12Axi | 3.399 (10) |
F13C···O12C | 2.882 (17) | C32···O12Aiv | 3.240 (11) |
F13C···O13C | 2.953 (18) | C32···O11Cxi | 3.040 (14) |
F11C···H32Av | 2.6200 | C32···C25 | 3.595 (8) |
F12A···H24i | 2.4000 | C32···O12Bxi | 3.256 (12) |
F12B···H24i | 2.1400 | C42A···C14ix | 3.567 (11) |
F12B···H43Cii | 2.7300 | C42A···F13C | 3.274 (16) |
F12B···H43Avii | 2.6700 | C42B···C30vi | 3.58 (2) |
F12C···H25v | 2.7100 | C43A···F12Bvii | 3.310 (15) |
F12C···H43Bvii | 2.6000 | C43A···O13Bix | 3.386 (16) |
F13A···H20Avi | 2.6000 | C43A···O13Cix | 2.593 (16) |
F13A···H12 | 2.5200 | C43A···F12Cvii | 3.133 (16) |
F13B···H12 | 2.7300 | C11···H30B | 2.5800 |
O1···N2i | 2.818 (5) | C11···H31D | 2.9000 |
O1···N1i | 2.873 (4) | C11···H30C | 2.9000 |
O1···Cl1 | 3.1785 (12) | C13···H43Cii | 3.0800 |
O1···N1 | 2.873 (4) | C20···H31B | 2.9200 |
O1···N2 | 2.818 (5) | C21···H31B | 2.6300 |
O1···N3 | 2.936 (4) | C21···H30D | 2.9300 |
O1···C10 | 3.169 (6) | C23···H31Axii | 2.9500 |
O1···C11 | 3.353 (5) | C25···H32A | 3.0600 |
O1···C20 | 3.206 (6) | C42A···H14ix | 2.8800 |
O1···C21 | 3.372 (5) | C42A···H30Cvi | 2.8100 |
O1···C10i | 3.169 (6) | H10A···O1 | 2.8500 |
O1···C11i | 3.353 (5) | H10A···H20B | 2.1500 |
O1···Cl1i | 3.1785 (12) | H10A···N41B | 2.9200 |
O1···C21i | 3.372 (5) | H10A···N41A | 2.9300 |
O1···N3i | 2.936 (4) | H10A···Cl1i | 2.8200 |
O1···C20i | 3.206 (6) | H10A···Fe1i | 3.5100 |
O2···S1Aiv | 3.457 (5) | H10B···N41Bvi | 2.7300 |
O2···N3 | 2.736 (5) | H10B···H30A | 2.5000 |
O2···N2 | 2.877 (6) | H10B···N41A | 2.8800 |
O2···N1 | 3.121 (5) | H10B···H12 | 2.5200 |
O2···O12Aiv | 3.065 (11) | H10B···N41Avi | 2.7900 |
O2···C30 | 2.337 (8) | H10B···H30B | 2.3800 |
O2···Cl1 | 3.167 (4) | H10B···N41B | 2.7800 |
O11A···F12A | 2.953 (17) | H10B···H30C | 2.0300 |
O11A···C23viii | 3.221 (14) | H12···F13A | 2.5200 |
O11A···F11A | 2.890 (17) | H12···H10B | 2.5200 |
O11B···C23viii | 3.217 (17) | H12···F13B | 2.7300 |
O11B···F12B | 2.92 (2) | H13···O13B | 2.4000 |
O11B···F11B | 3.05 (2) | H13···O13A | 2.6200 |
O11C···F12C | 2.959 (18) | H14···N41Bii | 2.7600 |
O11C···F11C | 2.962 (19) | H14···C42Aii | 2.8800 |
O11C···C32v | 3.040 (14) | H14···Cl1iii | 3.0700 |
O12A···F11A | 2.961 (14) | H15···Cl1 | 2.9600 |
O12A···C32v | 3.399 (10) | H20A···O12Avi | 2.5900 |
O12A···C22vi | 3.008 (13) | H20A···O12Cvi | 2.7000 |
O12A···O2iv | 3.065 (11) | H20A···H22 | 2.4900 |
O12A···C32iv | 3.240 (11) | H20A···H30A | 2.2400 |
O12A···F13A | 2.918 (13) | H20A···H30D | 2.2400 |
O12B···C22vi | 3.107 (15) | H20A···O12Bvi | 2.3900 |
O12B···C20vi | 3.261 (13) | H20A···F13Avi | 2.6000 |
O12B···F11B | 2.934 (17) | H20B···O1 | 2.9200 |
O12B···C32v | 3.256 (12) | H20B···H10A | 2.1500 |
O12B···F13B | 2.977 (16) | H20B···Cl1i | 2.8500 |
O12C···F11C | 2.948 (17) | H22···Cl1ix | 3.1000 |
O12C···F13C | 2.882 (17) | H22···H20A | 2.4900 |
O13A···F12A | 2.920 (13) | H22···O12Bvi | 2.4600 |
O13A···F13A | 2.950 (13) | H22···O12Avi | 2.2200 |
O13A···C30iv | 3.297 (11) | H23···O11Ax | 2.3300 |
O13B···C43Aii | 3.386 (16) | H23···O11Cx | 2.5600 |
O13B···F13B | 2.916 (17) | H23···H43Bxiii | 2.5800 |
O13B···C13 | 3.303 (13) | H23···O11Bx | 2.3500 |
O13B···F12B | 3.031 (16) | H24···F12Bi | 2.1400 |
O13C···F12C | 2.935 (17) | H24···O13Ci | 2.9000 |
O13C···C43Aii | 2.593 (16) | H24···F12Ai | 2.4000 |
O13C···F13C | 2.953 (18) | H25···Cl1 | 3.0600 |
O1···H10Ai | 2.8500 | H25···F12Cxi | 2.7100 |
O1···H20B | 2.9200 | H30A···H10B | 2.5000 |
O1···H20Bi | 2.9200 | H30A···H20A | 2.2400 |
O1···H10A | 2.8500 | H30B···H10B | 2.3800 |
O11A···H23viii | 2.3300 | H30B···N1 | 2.8900 |
O11A···H32Bv | 2.8400 | H30B···C11 | 2.5800 |
O11B···H43Bvii | 2.8000 | H30C···C11 | 2.9000 |
O11B···H23viii | 2.3500 | H30C···C42Avi | 2.8100 |
O11C···H43Bvii | 2.7300 | H30C···H10B | 2.0300 |
O11C···H23viii | 2.5600 | H30C···N41Avi | 2.5000 |
O11C···H32Bv | 2.4800 | H30D···H20A | 2.2400 |
O12A···H20Avi | 2.5900 | H30D···C21 | 2.9300 |
O12A···H22vi | 2.2200 | H31A···H32C | 2.4100 |
O12A···H32Civ | 2.8800 | H31A···C23xii | 2.9500 |
O12B···H20Avi | 2.3900 | H31B···N2 | 2.7600 |
O12B···H22vi | 2.4600 | H31B···C20 | 2.9200 |
O12B···H32Av | 2.8800 | H31B···H32A | 2.3000 |
O12C···H20Avi | 2.7000 | H31B···C21 | 2.6300 |
O13A···H13 | 2.6200 | H31C···H32C | 2.2800 |
O13B···H13 | 2.4000 | H31D···C11 | 2.9000 |
O13C···H43Cii | 2.0100 | H31D···N1 | 2.5800 |
O13C···H43Aii | 2.3600 | H32A···H31B | 2.3000 |
O13C···H24i | 2.9000 | H32A···O12Bxi | 2.8800 |
N1···O2 | 3.121 (5) | H32A···F11Cxi | 2.6200 |
N1···Cl1 | 3.396 (4) | H32A···C25 | 3.0600 |
N1···O1 | 2.873 (4) | H32B···Cl1 | 2.7600 |
N1···C30 | 3.238 (7) | H32B···O11Axi | 2.8400 |
N1···C10 | 2.415 (6) | H32B···O11Cxi | 2.4800 |
N1···C31B | 3.08 (2) | H32C···H32Cxiv | 2.5000 |
N1···N3 | 2.672 (5) | H32C···H31A | 2.4100 |
N2···C20 | 2.405 (8) | H32C···O12Aiv | 2.8800 |
N2···O1 | 2.818 (5) | H32C···H31C | 2.2800 |
N2···C31A | 3.151 (8) | H43A···F12Bvii | 2.6700 |
N2···Cl1 | 3.452 (5) | H43A···O13Cix | 2.3600 |
N2···C32 | 3.422 (7) | H43B···H23xiii | 2.5800 |
N2···C30 | 3.444 (8) | H43B···F12Cvii | 2.6000 |
N2···O2 | 2.877 (6) | H43B···O11Bvii | 2.8000 |
N2···N3 | 2.702 (6) | H43B···O11Cvii | 2.7300 |
N3···C11 | 2.441 (6) | H43C···C13ix | 3.0800 |
N3···N2 | 2.702 (6) | H43C···F12Bix | 2.7300 |
N3···O2 | 2.736 (5) | H43C···O13Cix | 2.0100 |
| | | |
Cl1—Fe1—O1 | 102.53 (4) | C12—C13—H13 | 121.00 |
Cl1—Fe1—O2 | 87.50 (11) | C14—C13—H13 | 121.00 |
Cl1—Fe1—N1 | 100.75 (10) | C15—C14—H14 | 120.00 |
Cl1—Fe1—N2 | 102.96 (13) | C13—C14—H14 | 120.00 |
Cl1—Fe1—N3 | 162.33 (10) | N1—C15—H15 | 119.00 |
O1—Fe1—O2 | 168.56 (11) | C14—C15—H15 | 119.00 |
O1—Fe1—N1 | 94.11 (10) | N3—C20—H20A | 110.00 |
O1—Fe1—N2 | 91.59 (13) | H20A—C20—H20B | 108.00 |
O1—Fe1—N3 | 95.09 (10) | N3—C20—H20B | 109.00 |
O2—Fe1—N1 | 89.33 (13) | C21—C20—H20A | 110.00 |
O2—Fe1—N2 | 80.67 (16) | C21—C20—H20B | 109.00 |
O2—Fe1—N3 | 75.08 (14) | C21—C22—H22 | 121.00 |
N1—Fe1—N2 | 153.76 (16) | C23—C22—H22 | 121.00 |
N1—Fe1—N3 | 76.52 (14) | C22—C23—H23 | 121.00 |
N2—Fe1—N3 | 77.47 (16) | C24—C23—H23 | 121.00 |
O12A—S1A—C1A | 103.5 (5) | C23—C24—H24 | 120.00 |
O13A—S1A—C1A | 106.2 (5) | C25—C24—H24 | 120.00 |
O11A—S1A—O12A | 110.2 (8) | C24—C25—H25 | 120.00 |
O11A—S1A—O13A | 116.4 (7) | N2—C25—H25 | 120.00 |
O11A—S1A—C1A | 107.1 (6) | N3—C30—H30C | 109.00 |
O12A—S1A—O13A | 112.5 (6) | N3—C30—H30A | 109.00 |
O11B—S1B—O13B | 107.0 (9) | N3—C30—H30B | 109.00 |
O11B—S1B—C1B | 116.4 (8) | C31A—C30—H30B | 109.00 |
O11B—S1B—O12B | 113.8 (10) | H30A—C30—H30B | 108.00 |
O12B—S1B—O13B | 109.1 (7) | C31B—C30—H30C | 109.00 |
O12B—S1B—C1B | 103.2 (6) | C31B—C30—H30D | 109.00 |
O13B—S1B—C1B | 107.0 (7) | H30C—C30—H30D | 108.00 |
O11C—S1C—O13C | 110.9 (8) | N3—C30—H30D | 109.00 |
O11C—S1C—C1C | 104.1 (7) | C31A—C30—H30A | 109.00 |
O12C—S1C—O13C | 113.4 (8) | C30—C31A—H31B | 111.00 |
O11C—S1C—O12C | 114.5 (8) | H31A—C31A—H31B | 109.00 |
O12C—S1C—C1C | 105.8 (7) | C30—C31A—H31A | 111.00 |
O13C—S1C—C1C | 107.3 (7) | O2—C31A—H31A | 111.00 |
Fe1—O1—Fe1i | 180.00 | O2—C31A—H31B | 111.00 |
Fe1—O2—C31B | 109.2 (10) | O2—C31B—H31D | 110.00 |
Fe1—O2—C31A | 110.7 (3) | C30—C31B—H31C | 110.00 |
Fe1—O2—C32 | 125.6 (3) | C30—C31B—H31D | 110.00 |
C31B—O2—C32 | 125.2 (11) | H31C—C31B—H31D | 109.00 |
C31A—O2—C32 | 106.7 (4) | O2—C31B—H31C | 110.00 |
Fe1—N1—C15 | 125.9 (3) | O2—C32—H32B | 110.00 |
Fe1—N1—C11 | 114.6 (3) | O2—C32—H32C | 110.00 |
C11—N1—C15 | 119.2 (4) | O2—C32—H32A | 110.00 |
Fe1—N2—C25 | 125.8 (4) | H32A—C32—H32C | 109.00 |
Fe1—N2—C21 | 115.8 (4) | H32B—C32—H32C | 109.00 |
C21—N2—C25 | 118.4 (5) | H32A—C32—H32B | 109.00 |
C10—N3—C20 | 111.7 (4) | S1A—C1A—F11A | 108.2 (6) |
C10—N3—C30 | 107.5 (4) | S1A—C1A—F12A | 104.6 (6) |
Fe1—N3—C30 | 112.2 (3) | S1A—C1A—F13A | 113.1 (6) |
Fe1—N3—C10 | 105.8 (3) | F11A—C1A—F12A | 105.4 (7) |
Fe1—N3—C20 | 106.2 (4) | F11A—C1A—F13A | 113.0 (8) |
C20—N3—C30 | 113.2 (4) | F12A—C1A—F13A | 111.9 (7) |
N3—C10—C11 | 110.0 (4) | S1B—C1B—F11B | 112.2 (8) |
N1—C11—C10 | 116.0 (4) | S1B—C1B—F12B | 107.8 (7) |
N1—C11—C12 | 121.7 (4) | S1B—C1B—F13B | 118.7 (8) |
C10—C11—C12 | 122.2 (4) | F11B—C1B—F12B | 96.7 (9) |
C11—C12—C13 | 119.2 (4) | F11B—C1B—F13B | 112.6 (10) |
C12—C13—C14 | 118.9 (5) | F12B—C1B—F13B | 106.2 (9) |
C13—C14—C15 | 119.4 (5) | S1C—C1C—F11C | 110.1 (8) |
N1—C15—C14 | 121.7 (4) | S1C—C1C—F12C | 110.7 (8) |
N3—C20—C21 | 110.8 (4) | S1C—C1C—F13C | 107.1 (8) |
N2—C21—C22 | 123.1 (7) | F11C—C1C—F12C | 111.8 (10) |
C20—C21—C22 | 121.1 (6) | F11C—C1C—F13C | 107.1 (10) |
N2—C21—C20 | 115.7 (5) | F12C—C1C—F13C | 109.8 (10) |
C21—C22—C23 | 118.7 (7) | N41A—C42A—C43A | 175.8 (12) |
C22—C23—C24 | 119.0 (7) | N41B—C42B—C43B | 173 (2) |
C23—C24—C25 | 120.6 (8) | C42A—C43A—H43A | 109.00 |
N2—C25—C24 | 120.3 (6) | C42A—C43A—H43B | 109.00 |
N3—C30—C31A | 113.6 (6) | C42A—C43A—H43C | 109.00 |
N3—C30—C31B | 114.3 (10) | H43A—C43A—H43B | 109.00 |
O2—C31A—C30 | 105.4 (5) | H43A—C43A—H43C | 109.00 |
O2—C31B—C30 | 107.5 (16) | H43B—C43A—H43C | 110.00 |
N3—C10—H10A | 110.00 | C42B—C43B—H43D | 109.00 |
C11—C10—H10A | 110.00 | C42B—C43B—H43E | 109.00 |
C11—C10—H10B | 110.00 | C42B—C43B—H43F | 109.00 |
N3—C10—H10B | 110.00 | H43D—C43B—H43E | 110.00 |
H10A—C10—H10B | 108.00 | H43D—C43B—H43F | 110.00 |
C11—C12—H12 | 120.00 | H43E—C43B—H43F | 109.00 |
C13—C12—H12 | 120.00 | | |
| | | |
Cl1—Fe1—O2—C31A | 166.2 (3) | N2—Fe1—N3—C30 | −94.2 (4) |
Cl1—Fe1—O2—C32 | 35.9 (4) | Fe1—O2—C31A—C30 | 41.5 (6) |
N1—Fe1—O2—C31A | −93.0 (4) | C32—O2—C31A—C30 | −178.9 (5) |
N1—Fe1—O2—C32 | 136.7 (4) | Fe1—N1—C11—C12 | 173.2 (4) |
N2—Fe1—O2—C31A | 62.7 (4) | Fe1—N1—C15—C14 | −172.8 (3) |
N2—Fe1—O2—C32 | −67.7 (4) | C15—N1—C11—C10 | −177.8 (4) |
N3—Fe1—O2—C31A | −16.8 (3) | C15—N1—C11—C12 | −0.3 (7) |
N3—Fe1—O2—C32 | −147.1 (4) | Fe1—N1—C11—C10 | −4.4 (5) |
Cl1—Fe1—N1—C11 | −175.6 (3) | C11—N1—C15—C14 | −0.1 (7) |
Cl1—Fe1—N1—C15 | −2.6 (4) | Fe1—N2—C21—C22 | −178.6 (5) |
O1—Fe1—N1—C11 | −72.0 (3) | C25—N2—C21—C20 | 176.3 (5) |
O1—Fe1—N1—C15 | 101.0 (3) | Fe1—N2—C21—C20 | −1.8 (6) |
O2—Fe1—N1—C11 | 97.1 (3) | Fe1—N2—C25—C24 | 178.0 (5) |
O2—Fe1—N1—C15 | −89.9 (4) | C21—N2—C25—C24 | 0.1 (9) |
N2—Fe1—N1—C11 | 30.1 (5) | C25—N2—C21—C22 | −0.5 (9) |
N2—Fe1—N1—C15 | −156.9 (4) | Fe1—N3—C20—C21 | −40.0 (5) |
N3—Fe1—N1—C11 | 22.3 (3) | C10—N3—C20—C21 | −154.9 (5) |
N3—Fe1—N1—C15 | −164.7 (4) | C30—N3—C20—C21 | 83.6 (6) |
Cl1—Fe1—N2—C21 | −178.4 (4) | Fe1—N3—C30—C31A | 40.3 (6) |
Cl1—Fe1—N2—C25 | 3.6 (5) | C10—N3—C30—C31A | 156.3 (5) |
O1—Fe1—N2—C21 | 78.4 (4) | C20—N3—C30—C31A | −79.9 (6) |
O1—Fe1—N2—C25 | −99.6 (5) | Fe1—N3—C10—C11 | 42.7 (4) |
O2—Fe1—N2—C21 | −93.2 (4) | C20—N3—C10—C11 | 157.7 (4) |
O2—Fe1—N2—C25 | 88.9 (5) | C30—N3—C10—C11 | −77.5 (5) |
N1—Fe1—N2—C21 | −24.3 (6) | N3—C10—C11—C12 | 155.6 (4) |
N1—Fe1—N2—C25 | 157.8 (4) | N3—C10—C11—N1 | −26.9 (6) |
N3—Fe1—N2—C21 | −16.5 (4) | C10—C11—C12—C13 | 177.7 (4) |
N3—Fe1—N2—C25 | 165.5 (5) | N1—C11—C12—C13 | 0.3 (7) |
O1—Fe1—N3—C10 | 58.4 (3) | C11—C12—C13—C14 | 0.1 (7) |
O1—Fe1—N3—C20 | −60.4 (3) | C12—C13—C14—C15 | −0.4 (7) |
O1—Fe1—N3—C30 | 175.4 (3) | C13—C14—C15—N1 | 0.5 (7) |
O2—Fe1—N3—C10 | −127.6 (3) | N3—C20—C21—N2 | 29.3 (7) |
O2—Fe1—N3—C20 | 113.6 (3) | N3—C20—C21—C22 | −153.9 (6) |
O2—Fe1—N3—C30 | −10.6 (3) | C20—C21—C22—C23 | −176.6 (6) |
N1—Fe1—N3—C10 | −34.7 (3) | N2—C21—C22—C23 | 0.1 (10) |
N1—Fe1—N3—C20 | −153.5 (3) | C21—C22—C23—C24 | 0.7 (11) |
N1—Fe1—N3—C30 | 82.3 (3) | C22—C23—C24—C25 | −1.1 (12) |
N2—Fe1—N3—C10 | 148.9 (3) | C23—C24—C25—N2 | 0.7 (11) |
N2—Fe1—N3—C20 | 30.1 (3) | N3—C30—C31A—O2 | −53.6 (6) |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) x−1, y, z; (iii) −x, −y, −z+1; (iv) −x, −y+1, −z+1; (v) x, y+1, z−1; (vi) −x+1, −y+1, −z+1; (vii) −x+1, −y+1, −z; (viii) x−1, y+1, z−1; (ix) x+1, y, z; (x) x+1, y−1, z+1; (xi) x, y−1, z+1; (xii) −x+1, −y, −z+2; (xiii) −x+2, −y, −z+1; (xiv) −x, −y, −z+2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10A···Cl1i | 0.99 | 2.82 | 3.781 (5) | 164 |
C32—H32B···Cl1 | 0.98 | 2.76 | 3.385 (5) | 122 |
Symmetry code: (i) −x+1, −y, −z+1. |