metal-organic compounds
The crystal structure of the title compound, [Fe(C11H9O2N2)2]BF4·3H2O, contains two independent bis[di-2-pyridyl(hydroxy)methanolato-κ3O,N,N′)]iron(III) cations, with the Fe atom occupying a special position of symmetry in each case; the Fe atom is O,N,N′-chelated by the anionic ligands in an octahedral geometry. The cation, the disordered BF4− counter-ion and the uncoordinated water molecules interact via hydrogen bonds to form a sheet motif.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805002369/hb6146sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805002369/hb6146Isup2.hkl |
CCDC reference: 263582
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.007 Å
- R factor = 0.067
- wR factor = 0.172
- Data-to-parameter ratio = 12.4
checkCIF/PLATON results
No syntax errors found
Alert level A PLAT241_ALERT_2_A Check High Ueq as Compared to Neighbors for F1'
Author Response: The [BF~4~] ion is disordered over two sites. The disordered is described. |
PLAT241_ALERT_2_A Check High Ueq as Compared to Neighbors for F2
Author Response: The [BF~4~] ion is disordered over two sites. The disordered is described. |
PLAT241_ALERT_2_A Check High Ueq as Compared to Neighbors for F2'
Author Response: The [BF~4~] ion is disordered over two sites. The disordered is described. |
PLAT241_ALERT_2_A Check High Ueq as Compared to Neighbors for F3
Author Response: The [BF~4~] ion is disordered over two sites. The disordered is described. |
PLAT242_ALERT_2_A Check Low Ueq as Compared to Neighbors for B1 PLAT242_ALERT_2_A Check Low Ueq as Compared to Neighbors for B1'
Alert level B PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for F3'
Author Response: The [BF~4~] ion is disordered over two sites. The disordered is described. |
PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for F4'
Author Response: The [BF~4~] ion is disordered over two sites. The disordered is described. |
PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for F1 PLAT731_ALERT_1_B Bond Calc 0.86(5), Rep 0.850(10) ...... 5.00 su-Rat O1W -H1W2 1.555 1.555 PLAT735_ALERT_1_B D-H Calc 0.86(5), Rep 0.850(10) ...... 5.00 su-Rat O1W -H2# 1.555 1.555 PLAT735_ALERT_1_B D-H Calc 0.86(5), Rep 0.850(10) ...... 5.00 su-Rat O1W -H2# 1.555 1.555
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.03 PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT301_ALERT_3_C Main Residue Disorder ......................... 7.00 Perc. PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 6 PLAT731_ALERT_1_C Bond Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Rat O2 -H2O 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.84(4), Rep 0.850(10) ...... 4.00 su-Rat O4 -H4O 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.85(4), Rep 0.850(10) ...... 4.00 su-Rat O1W -H1W1 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.86(4), Rep 0.850(10) ...... 4.00 su-Rat O2W -H2W1 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.85(4), Rep 0.850(10) ...... 4.00 su-Rat O2W -H2W2 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.85(4), Rep 0.850(10) ...... 4.00 su-Rat O3W -H3W1 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.84(4), Rep 0.850(10) ...... 4.00 su-Rat O3W -H3W2 1.555 1.555 PLAT732_ALERT_1_C Angle Calc 109(5), Rep 109(2) ...... 2.50 su-Rat H1W1 -O1W -H1W2 1.555 1.555 1.555 PLAT732_ALERT_1_C Angle Calc 111(5), Rep 110(2) ...... 2.50 su-Rat H3W1 -O3W -H3W2 1.555 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Rat O2 -H2O 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.84(4), Rep 0.850(10) ...... 4.00 su-Rat O4 -H4O 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.85(4), Rep 0.850(10) ...... 4.00 su-Rat O1W -H1# 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.86(4), Rep 0.850(10) ...... 4.00 su-Rat O2W -H3# 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.85(4), Rep 0.850(10) ...... 4.00 su-Rat O2W -H4# 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.85(4), Rep 0.850(10) ...... 4.00 su-Rat O2W -H4# 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.85(4), Rep 0.850(10) ...... 4.00 su-Rat O3W -H5# 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.85(4), Rep 0.850(10) ...... 4.00 su-Rat O3W -H5# 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.84(4), Rep 0.850(10) ...... 4.00 su-Rat O3W -H6# 1.555 1.555 PLAT736_ALERT_1_C H...A Calc 1.86(3), Rep 1.860(10) ...... 3.00 su-Rat H2O -O3W 1.555 1.555 PLAT736_ALERT_1_C H...A Calc 1.78(4), Rep 1.770(10) ...... 4.00 su-Rat H4O -O1W 1.555 1.545 PLAT736_ALERT_1_C H...A Calc 1.89(5), Rep 1.89(2) ...... 2.50 su-Rat H3# -O3 1.555 1.555 PLAT736_ALERT_1_C H...A Calc 1.96(3), Rep 1.960(10) ...... 3.00 su-Rat H6# -O2W 1.555 1.555
6 ALERT level A = In general: serious problem 6 ALERT level B = Potentially serious problem 28 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 27 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 10 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); 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(C11H9O2N2)2]BF4·3H2O | Z = 2 |
Mr = 599.11 | F(000) = 614 |
Triclinic, P1 | Dx = 1.538 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.9669 (6) Å | Cell parameters from 3106 reflections |
b = 9.0527 (6) Å | θ = 2.3–26.2° |
c = 16.295 (1) Å | µ = 0.66 mm−1 |
α = 86.608 (1)° | T = 298 K |
β = 78.840 (1)° | Block, orange |
γ = 86.593 (1)° | 0.23 × 0.10 × 0.07 mm |
V = 1293.9 (2) Å3 |
Data collection top
Bruker APEX area-detector diffractometer | 5202 independent reflections |
Radiation source: fine-focus sealed tube | 4175 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
φ and ω scans | θmax = 26.3°, θmin = 1.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −11→11 |
Tmin = 0.793, Tmax = 0.955 | k = −11→11 |
13700 measured reflections | l = −20→20 |
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)] = 0.067 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.172 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.14 | w = 1/[σ2(Fo2) + (0.0799P)2 + 0.9114P] where P = (Fo2 + 2Fc2)/3 |
5202 reflections | (Δ/σ)max = 0.001 |
418 parameters | Δρmax = 0.77 e Å−3 |
79 restraints | Δρmin = −0.38 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Fe1 | 0.5000 | 0.5000 | 0.5000 | 0.0278 (2) | |
Fe2 | 0.5000 | 0.0000 | 0.0000 | 0.0297 (2) | |
F1 | 0.1627 (8) | 0.6763 (10) | 0.2269 (5) | 0.094 (2) | 0.50 |
F2 | 0.0527 (14) | 0.8486 (10) | 0.3128 (8) | 0.171 (5) | 0.50 |
F3 | −0.0813 (12) | 0.7478 (18) | 0.2314 (8) | 0.187 (6) | 0.50 |
F4 | −0.0130 (12) | 0.6212 (9) | 0.3412 (5) | 0.111 (3) | 0.50 |
F1' | 0.0802 (16) | 0.6217 (14) | 0.1888 (7) | 0.199 (6) | 0.50 |
F2' | 0.0930 (16) | 0.6453 (17) | 0.3222 (9) | 0.208 (7) | 0.50 |
F3' | −0.0029 (15) | 0.8361 (10) | 0.2490 (9) | 0.158 (5) | 0.50 |
F4' | −0.1266 (10) | 0.6315 (12) | 0.2852 (7) | 0.143 (4) | 0.50 |
O1 | 0.4994 (3) | 0.5106 (3) | 0.3858 (2) | 0.0343 (6) | |
O2 | 0.5769 (4) | 0.3521 (4) | 0.2752 (2) | 0.0490 (8) | |
O3 | 0.4525 (3) | 0.0019 (3) | 0.1160 (2) | 0.0355 (6) | |
O4 | 0.5847 (4) | −0.0585 (4) | 0.2253 (2) | 0.0471 (8) | |
O1w | 0.3945 (5) | 0.7581 (4) | 0.3135 (3) | 0.0695 (11) | |
O2w | 0.1869 (5) | 0.0942 (4) | 0.2157 (3) | 0.0750 (12) | |
O3w | 0.2985 (5) | 0.3702 (5) | 0.2331 (3) | 0.0831 (13) | |
N1 | 0.4172 (4) | 0.3059 (3) | 0.4941 (2) | 0.0318 (7) | |
N2 | 0.7017 (4) | 0.4014 (3) | 0.4636 (2) | 0.0311 (7) | |
N3 | 0.5913 (4) | −0.1965 (3) | 0.0237 (2) | 0.0314 (7) | |
N4 | 0.6914 (4) | 0.0782 (4) | 0.0170 (2) | 0.0343 (8) | |
C1 | 0.3317 (5) | 0.2237 (5) | 0.5533 (3) | 0.0397 (10) | |
C2 | 0.2820 (5) | 0.0902 (5) | 0.5351 (3) | 0.0500 (12) | |
C3 | 0.3201 (6) | 0.0413 (5) | 0.4548 (3) | 0.0520 (12) | |
C4 | 0.4093 (5) | 0.1264 (5) | 0.3938 (3) | 0.0447 (11) | |
C5 | 0.4551 (4) | 0.2596 (4) | 0.4156 (2) | 0.0326 (9) | |
C6 | 0.5592 (5) | 0.3692 (5) | 0.3599 (3) | 0.0381 (9) | |
C7 | 0.7110 (5) | 0.3457 (4) | 0.3883 (3) | 0.0349 (9) | |
C8 | 0.8404 (5) | 0.2719 (5) | 0.3482 (3) | 0.0482 (11) | |
C9 | 0.9641 (5) | 0.2539 (6) | 0.3882 (3) | 0.0552 (13) | |
C10 | 0.9527 (5) | 0.3109 (5) | 0.4657 (3) | 0.0502 (12) | |
C11 | 0.8206 (5) | 0.3857 (5) | 0.5022 (3) | 0.0385 (10) | |
C12 | 0.6212 (5) | −0.3127 (5) | −0.0251 (3) | 0.0417 (10) | |
C13 | 0.6834 (6) | −0.4441 (5) | 0.0043 (3) | 0.0565 (13) | |
C14 | 0.7083 (6) | −0.4555 (5) | 0.0850 (4) | 0.0582 (13) | |
C15 | 0.6790 (5) | −0.3351 (5) | 0.1344 (3) | 0.0479 (11) | |
C16 | 0.6206 (5) | −0.2069 (4) | 0.1013 (3) | 0.0347 (9) | |
C17 | 0.5878 (5) | −0.0558 (5) | 0.1408 (2) | 0.0361 (9) | |
C18 | 0.7139 (5) | 0.0404 (4) | 0.0949 (3) | 0.0363 (9) | |
C19 | 0.8396 (5) | 0.0816 (5) | 0.1231 (3) | 0.0473 (11) | |
C20 | 0.9436 (6) | 0.1658 (6) | 0.0698 (4) | 0.0564 (13) | |
C21 | 0.9195 (5) | 0.2052 (5) | −0.0094 (3) | 0.0525 (12) | |
C22 | 0.7920 (5) | 0.1582 (4) | −0.0354 (3) | 0.0393 (10) | |
B1 | 0.0298 (11) | 0.7209 (12) | 0.2767 (6) | 0.068 (3) | 0.50 |
B1' | 0.0138 (12) | 0.6864 (13) | 0.2607 (7) | 0.068 (3) | 0.50 |
H2o | 0.489 (3) | 0.357 (6) | 0.263 (3) | 0.059* | |
H4o | 0.518 (4) | −0.113 (5) | 0.253 (3) | 0.057* | |
H1w1 | 0.439 (6) | 0.680 (3) | 0.330 (4) | 0.083* | |
H1w2 | 0.324 (5) | 0.734 (5) | 0.289 (4) | 0.083* | |
H2w1 | 0.277 (3) | 0.066 (5) | 0.192 (4) | 0.090* | |
H2w2 | 0.133 (5) | 0.019 (4) | 0.228 (4) | 0.090* | |
H3w1 | 0.234 (5) | 0.443 (4) | 0.239 (4) | 0.100* | |
H3w2 | 0.255 (6) | 0.291 (3) | 0.231 (4) | 0.100* | |
H1 | 0.3051 | 0.2565 | 0.6075 | 0.048* | |
H2 | 0.2228 | 0.0331 | 0.5770 | 0.060* | |
H3 | 0.2860 | −0.0480 | 0.4420 | 0.062* | |
H4 | 0.4379 | 0.0952 | 0.3393 | 0.054* | |
H8 | 0.8451 | 0.2349 | 0.2957 | 0.058* | |
H9 | 1.0534 | 0.2041 | 0.3630 | 0.066* | |
H10 | 1.0343 | 0.2988 | 0.4934 | 0.060* | |
H11 | 0.8141 | 0.4256 | 0.5542 | 0.046* | |
H12 | 0.6001 | −0.3051 | −0.0789 | 0.050* | |
H13 | 0.7080 | −0.5237 | −0.0301 | 0.068* | |
H14 | 0.7452 | −0.5449 | 0.1063 | 0.070* | |
H15 | 0.6982 | −0.3406 | 0.1886 | 0.057* | |
H19 | 0.8542 | 0.0532 | 0.1769 | 0.057* | |
H20 | 1.0293 | 0.1957 | 0.0873 | 0.068* | |
H21 | 0.9883 | 0.2631 | −0.0456 | 0.063* | |
H22 | 0.7769 | 0.1827 | −0.0895 | 0.047* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Fe1 | 0.0314 (4) | 0.0253 (4) | 0.0271 (4) | −0.0005 (3) | −0.0069 (3) | −0.0006 (3) |
Fe2 | 0.0325 (4) | 0.0240 (4) | 0.0313 (4) | 0.0016 (3) | −0.0037 (3) | −0.0008 (3) |
F1 | 0.070 (4) | 0.132 (6) | 0.073 (5) | 0.009 (4) | 0.000 (4) | 0.005 (4) |
F2 | 0.195 (9) | 0.147 (8) | 0.174 (9) | −0.032 (7) | −0.033 (7) | −0.018 (7) |
F3 | 0.156 (8) | 0.227 (10) | 0.204 (9) | 0.003 (8) | −0.107 (8) | 0.021 (8) |
F4 | 0.127 (7) | 0.115 (6) | 0.089 (5) | −0.032 (5) | −0.018 (5) | 0.044 (5) |
F1' | 0.234 (10) | 0.196 (10) | 0.150 (9) | 0.027 (8) | −0.003 (8) | −0.010 (7) |
F2' | 0.196 (10) | 0.255 (11) | 0.201 (10) | −0.032 (8) | −0.121 (8) | 0.048 (8) |
F3' | 0.171 (9) | 0.112 (7) | 0.193 (9) | −0.025 (7) | −0.046 (7) | 0.024 (7) |
F4' | 0.127 (7) | 0.148 (7) | 0.160 (8) | −0.042 (6) | −0.044 (6) | 0.028 (6) |
O1 | 0.0413 (16) | 0.0321 (15) | 0.0301 (14) | 0.0012 (12) | −0.0089 (12) | −0.0011 (11) |
O2 | 0.060 (2) | 0.057 (2) | 0.0303 (16) | −0.0032 (17) | −0.0080 (15) | −0.0081 (14) |
O3 | 0.0339 (15) | 0.0347 (15) | 0.0352 (15) | 0.0053 (12) | −0.0017 (12) | −0.0024 (12) |
O4 | 0.060 (2) | 0.0481 (19) | 0.0331 (17) | 0.0004 (15) | −0.0106 (15) | −0.0018 (14) |
O1w | 0.073 (3) | 0.055 (2) | 0.080 (3) | −0.0023 (19) | −0.023 (2) | 0.028 (2) |
O2w | 0.053 (2) | 0.073 (3) | 0.093 (3) | 0.0047 (19) | 0.006 (2) | −0.029 (2) |
O3w | 0.079 (3) | 0.079 (3) | 0.098 (3) | −0.002 (2) | −0.031 (3) | −0.019 (3) |
N1 | 0.0318 (17) | 0.0284 (17) | 0.0363 (18) | 0.0009 (13) | −0.0093 (14) | −0.0026 (14) |
N2 | 0.0328 (17) | 0.0271 (17) | 0.0326 (18) | −0.0010 (13) | −0.0050 (14) | −0.0009 (14) |
N3 | 0.0333 (18) | 0.0252 (17) | 0.0347 (18) | 0.0016 (13) | −0.0049 (14) | −0.0015 (14) |
N4 | 0.0351 (18) | 0.0267 (17) | 0.0401 (19) | −0.0008 (14) | −0.0048 (15) | −0.0032 (14) |
C1 | 0.035 (2) | 0.038 (2) | 0.044 (2) | −0.0027 (18) | −0.0035 (18) | 0.0046 (19) |
C2 | 0.045 (3) | 0.036 (2) | 0.068 (3) | −0.008 (2) | −0.010 (2) | 0.010 (2) |
C3 | 0.054 (3) | 0.033 (2) | 0.073 (4) | −0.008 (2) | −0.019 (3) | −0.007 (2) |
C4 | 0.049 (3) | 0.035 (2) | 0.053 (3) | 0.000 (2) | −0.016 (2) | −0.011 (2) |
C5 | 0.035 (2) | 0.027 (2) | 0.037 (2) | 0.0003 (16) | −0.0112 (17) | −0.0023 (16) |
C6 | 0.046 (2) | 0.036 (2) | 0.031 (2) | 0.0016 (18) | −0.0061 (18) | −0.0061 (17) |
C7 | 0.042 (2) | 0.025 (2) | 0.036 (2) | −0.0018 (17) | −0.0041 (18) | −0.0013 (17) |
C8 | 0.050 (3) | 0.042 (3) | 0.047 (3) | −0.001 (2) | 0.005 (2) | −0.008 (2) |
C9 | 0.037 (3) | 0.052 (3) | 0.070 (3) | 0.006 (2) | 0.006 (2) | −0.006 (3) |
C10 | 0.031 (2) | 0.052 (3) | 0.066 (3) | 0.002 (2) | −0.009 (2) | 0.001 (2) |
C11 | 0.037 (2) | 0.036 (2) | 0.044 (2) | −0.0043 (18) | −0.0131 (19) | 0.0031 (19) |
C12 | 0.051 (3) | 0.030 (2) | 0.044 (3) | 0.0012 (19) | −0.009 (2) | −0.0054 (19) |
C13 | 0.069 (3) | 0.030 (2) | 0.070 (4) | 0.010 (2) | −0.012 (3) | −0.011 (2) |
C14 | 0.067 (3) | 0.034 (3) | 0.072 (4) | 0.013 (2) | −0.017 (3) | 0.003 (2) |
C15 | 0.054 (3) | 0.041 (3) | 0.050 (3) | 0.008 (2) | −0.018 (2) | 0.005 (2) |
C16 | 0.035 (2) | 0.030 (2) | 0.037 (2) | −0.0015 (17) | −0.0044 (17) | 0.0020 (17) |
C17 | 0.042 (2) | 0.035 (2) | 0.030 (2) | 0.0051 (18) | −0.0055 (17) | −0.0031 (17) |
C18 | 0.042 (2) | 0.028 (2) | 0.039 (2) | 0.0019 (17) | −0.0084 (18) | −0.0060 (17) |
C19 | 0.051 (3) | 0.042 (3) | 0.053 (3) | 0.001 (2) | −0.019 (2) | −0.011 (2) |
C20 | 0.047 (3) | 0.047 (3) | 0.080 (4) | −0.001 (2) | −0.020 (3) | −0.016 (3) |
C21 | 0.043 (3) | 0.036 (3) | 0.075 (4) | −0.006 (2) | 0.000 (2) | −0.005 (2) |
C22 | 0.038 (2) | 0.030 (2) | 0.048 (3) | −0.0005 (17) | −0.0024 (19) | −0.0027 (18) |
B1 | 0.058 (5) | 0.085 (8) | 0.065 (6) | −0.008 (5) | −0.031 (5) | 0.026 (6) |
B1' | 0.058 (5) | 0.085 (8) | 0.065 (6) | −0.008 (5) | −0.031 (5) | 0.026 (6) |
Geometric parameters (Å, º) top
Fe1—O1 | 1.858 (3) | C16—C17 | 1.535 (6) |
Fe1—O1i | 1.858 (3) | C17—C18 | 1.519 (6) |
Fe1—N1 | 1.962 (3) | C18—C19 | 1.376 (6) |
Fe1—N1i | 1.962 (3) | C19—C20 | 1.377 (7) |
Fe1—N2 | 1.969 (3) | C20—C21 | 1.372 (7) |
Fe1—N2i | 1.969 (3) | C21—C22 | 1.390 (6) |
Fe2—O3 | 1.856 (3) | F1—B1 | 1.360 (9) |
Fe2—O3ii | 1.856 (3) | F2—B1 | 1.371 (9) |
Fe2—N3 | 1.963 (3) | F3—B1 | 1.353 (9) |
Fe2—N3ii | 1.963 (3) | F4—B1 | 1.356 (9) |
Fe2—N4 | 1.969 (3) | F1'—B1' | 1.357 (9) |
Fe2—N4ii | 1.969 (3) | F2'—B1' | 1.357 (9) |
O1—C6 | 1.414 (5) | F3'—B1' | 1.361 (9) |
O2—C6 | 1.375 (5) | F4'—B1' | 1.359 (9) |
O3—C17 | 1.413 (5) | O2—H2o | 0.85 (1) |
O4—C17 | 1.372 (5) | O4—H4o | 0.85 (1) |
N1—C1 | 1.330 (5) | O1w—H1w1 | 0.85 (1) |
N1—C5 | 1.345 (5) | O1w—H1w2 | 0.85 (1) |
N2—C11 | 1.336 (5) | O2w—H2w1 | 0.85 (1) |
N2—C7 | 1.340 (5) | O2w—H2w2 | 0.85 (1) |
N3—C16 | 1.337 (5) | O3w—H3w1 | 0.85 (1) |
N3—C12 | 1.339 (5) | O3w—H3w2 | 0.85 (1) |
N4—C22 | 1.331 (5) | C1—H1 | 0.93 |
N4—C18 | 1.344 (5) | C2—H2 | 0.93 |
C1—C2 | 1.381 (6) | C3—H3 | 0.93 |
C2—C3 | 1.379 (7) | C4—H4 | 0.93 |
C3—C4 | 1.377 (7) | C8—H8 | 0.93 |
C4—C5 | 1.383 (6) | C9—H9 | 0.93 |
C5—C6 | 1.534 (6) | C10—H10 | 0.93 |
C6—C7 | 1.520 (6) | C11—H11 | 0.93 |
C7—C8 | 1.373 (6) | C12—H12 | 0.93 |
C8—C9 | 1.388 (7) | C13—H13 | 0.93 |
C9—C10 | 1.375 (7) | C14—H14 | 0.93 |
C10—C11 | 1.377 (6) | C15—H15 | 0.93 |
C12—C13 | 1.383 (6) | C19—H19 | 0.93 |
C13—C14 | 1.372 (7) | C20—H20 | 0.93 |
C14—C15 | 1.376 (7) | C21—H21 | 0.93 |
C15—C16 | 1.369 (6) | C22—H22 | 0.93 |
O1—Fe1—O1i | 180 | C16—C15—C14 | 117.9 (4) |
O1—Fe1—N1 | 82.6 (1) | N3—C16—C15 | 122.2 (4) |
O1—Fe1—N1i | 97.4 (1) | N3—C16—C17 | 109.6 (3) |
O1—Fe1—N2 | 82.7 (1) | C15—C16—C17 | 128.1 (4) |
O1—Fe1—N2i | 97.3 (1) | O4—C17—O3 | 114.8 (3) |
O1i—Fe1—N1 | 97.4 (1) | O4—C17—C18 | 109.9 (3) |
O1i—Fe1—N1i | 82.6 (1) | O3—C17—C18 | 106.2 (3) |
O1i—Fe1—N2 | 97.3 (1) | O4—C17—C16 | 114.9 (3) |
O1i—Fe1—N2i | 82.7 (1) | O3—C17—C16 | 105.0 (3) |
N1i—Fe1—N1 | 180 | C18—C17—C16 | 105.2 (3) |
N1—Fe1—N2 | 86.3 (1) | N4—C18—C19 | 121.9 (4) |
N1—Fe1—N2i | 93.7 (1) | N4—C18—C17 | 110.2 (3) |
N1i—Fe1—N2i | 86.3 (1) | C19—C18—C17 | 127.9 (4) |
N1i—Fe1—N2 | 93.7 (1) | C20—C19—C18 | 118.5 (5) |
N2—Fe1—N2i | 180 | C21—C20—C19 | 119.4 (5) |
O3—Fe2—O3ii | 180 | C20—C21—C22 | 119.9 (5) |
O3—Fe2—N3 | 82.7 (1) | N4—C22—C21 | 120.2 (4) |
O3—Fe2—N3ii | 97.3 (1) | F3—B1—F4 | 111.1 (9) |
O3—Fe2—N4 | 82.6 (1) | F3—B1—F1 | 110.8 (8) |
O3—Fe2—N4ii | 97.4 (1) | F4—B1—F1 | 111.6 (8) |
O3ii—Fe2—N3 | 97.3 (1) | F3—B1—F2 | 109.2 (8) |
O3ii—Fe2—N3ii | 82.7 (1) | F4—B1—F2 | 105.7 (8) |
O3ii—Fe2—N4 | 97.4 (1) | F1—B1—F2 | 108.4 (8) |
O3ii—Fe2—N4ii | 82.6 (1) | F2'—B1'—F4' | 106.7 (8) |
N3—Fe2—N3ii | 180 | F2'—B1'—F3' | 112.7 (9) |
N3—Fe2—N4 | 86.1 (1) | F4'—B1'—F3' | 108.4 (8) |
N3—Fe2—N4ii | 93.9 (1) | F2'—B1'—F1' | 109.8 (9) |
N3ii—Fe2—N4 | 93.9 (1) | F4'—B1'—F1' | 107.3 (8) |
N3ii—Fe2—N4ii | 86.1 (1) | F3'—B1'—F1' | 111.7 (8) |
N4—Fe2—N4ii | 180 | C6—O2—H2o | 107 (4) |
C6—O1—Fe1 | 103.4 (2) | C17—O4—H4o | 113 (4) |
C17—O3—Fe2 | 103.3 (2) | H1w1—O1w—H1w2 | 109 (2) |
C1—N1—C5 | 120.0 (4) | H2w1—O2w—H2w2 | 109 (2) |
C1—N1—Fe1 | 130.0 (3) | H3w1—O3w—H3w2 | 110 (2) |
C5—N1—Fe1 | 110.0 (3) | N1—C1—H1 | 119.7 |
C11—N2—C7 | 120.1 (4) | C2—C1—H1 | 119.7 |
C11—N2—Fe1 | 129.7 (3) | C1—C2—H2 | 120.0 |
C7—N2—Fe1 | 110.3 (3) | C3—C2—H2 | 120.0 |
C16—N3—C12 | 120.3 (3) | C4—C3—H3 | 120.4 |
C16—N3—Fe2 | 110.6 (2) | C2—C3—H3 | 120.4 |
C12—N3—Fe2 | 129.1 (3) | C3—C4—H4 | 120.9 |
C22—N4—C18 | 120.2 (4) | C5—C4—H4 | 120.9 |
C22—N4—Fe2 | 129.8 (3) | C7—C8—H8 | 120.9 |
C18—N4—Fe2 | 110.0 (3) | C9—C8—H8 | 120.9 |
N1—C1—C2 | 120.6 (4) | C10—C9—H9 | 120.5 |
C1—C2—C3 | 120.0 (4) | C8—C9—H9 | 120.5 |
C4—C3—C2 | 119.2 (4) | C11—C10—H10 | 120.0 |
C3—C4—C5 | 118.2 (4) | C9—C10—H10 | 120.0 |
N1—C5—C4 | 122.0 (4) | N2—C11—H11 | 119.8 |
N1—C5—C6 | 110.2 (3) | C10—C11—H11 | 119.8 |
C4—C5—C6 | 127.7 (4) | N3—C12—H12 | 119.9 |
O2—C6—O1 | 114.4 (3) | C13—C12—H12 | 119.9 |
O2—C6—C7 | 110.7 (3) | C14—C13—H13 | 120.4 |
O1—C6—C7 | 106.3 (3) | C12—C13—H13 | 120.4 |
O2—C6—C5 | 115.1 (3) | C15—C14—H14 | 119.9 |
O1—C6—C5 | 104.8 (3) | C13—C14—H14 | 119.9 |
C7—C6—C5 | 104.7 (3) | C16—C15—H15 | 121.1 |
N2—C7—C8 | 122.1 (4) | C14—C15—H15 | 121.1 |
N2—C7—C6 | 110.2 (3) | C20—C19—H19 | 120.8 |
C8—C7—C6 | 127.6 (4) | C18—C19—H19 | 120.8 |
C7—C8—C9 | 118.2 (4) | C21—C20—H20 | 120.3 |
C10—C9—C8 | 119.0 (4) | C19—C20—H20 | 120.3 |
C11—C10—C9 | 120.1 (4) | C20—C21—H21 | 120.1 |
N2—C11—C10 | 120.4 (4) | C22—C21—H21 | 120.1 |
N3—C12—C13 | 120.1 (4) | N4—C22—H22 | 119.9 |
C14—C13—C12 | 119.2 (4) | C21—C22—H22 | 119.9 |
C15—C14—C13 | 120.3 (4) | ||
N1i—Fe1—O1—C6 | 135.6 (2) | C4—C5—C6—O1 | 144.2 (4) |
N1—Fe1—O1—C6 | −44.4 (2) | N1—C5—C6—C7 | 72.4 (4) |
N2i—Fe1—O1—C6 | −137.2 (2) | C4—C5—C6—C7 | −104.1 (5) |
N2—Fe1—O1—C6 | 42.8 (2) | C11—N2—C7—C8 | −0.2 (6) |
N3—Fe2—O3—C17 | 43.5 (2) | Fe1—N2—C7—C8 | 179.6 (3) |
N3ii—Fe2—O3—C17 | −136.5 (2) | C11—N2—C7—C6 | 176.5 (3) |
N4ii—Fe2—O3—C17 | 136.5 (2) | Fe1—N2—C7—C6 | −3.7 (4) |
N4—Fe2—O3—C17 | −43.5 (2) | O2—C6—C7—N2 | 162.9 (3) |
O1—Fe1—N1—C1 | −155.4 (4) | O1—C6—C7—N2 | 38.2 (4) |
O1i—Fe1—N1—C1 | 24.6 (4) | C5—C6—C7—N2 | −72.4 (4) |
N2i—Fe1—N1—C1 | −58.6 (4) | O2—C6—C7—C8 | −20.6 (6) |
N2—Fe1—N1—C1 | 121.4 (4) | O1—C6—C7—C8 | −145.3 (4) |
O1—Fe1—N1—C5 | 22.6 (3) | C5—C6—C7—C8 | 104.1 (5) |
O1i—Fe1—N1—C5 | −157.4 (3) | N2—C7—C8—C9 | 0.7 (6) |
N2i—Fe1—N1—C5 | 119.5 (3) | C6—C7—C8—C9 | −175.4 (4) |
N2—Fe1—N1—C5 | −60.5 (3) | C7—C8—C9—C10 | −0.3 (7) |
O1—Fe1—N2—C11 | 157.5 (4) | C8—C9—C10—C11 | −0.6 (7) |
O1i—Fe1—N2—C11 | −22.5 (4) | C7—N2—C11—C10 | −0.8 (6) |
N1i—Fe1—N2—C11 | 60.5 (3) | Fe1—N2—C11—C10 | 179.5 (3) |
N1—Fe1—N2—C11 | −119.5 (3) | C9—C10—C11—N2 | 1.2 (7) |
O1—Fe1—N2—C7 | −22.2 (3) | C16—N3—C12—C13 | −0.3 (6) |
O1i—Fe1—N2—C7 | 157.8 (3) | Fe2—N3—C12—C13 | −178.5 (3) |
N1i—Fe1—N2—C7 | −119.2 (3) | N3—C12—C13—C14 | 2.5 (8) |
N1—Fe1—N2—C7 | 60.8 (3) | C12—C13—C14—C15 | −3.3 (8) |
O3ii—Fe2—N3—C16 | 158.9 (3) | C13—C14—C15—C16 | 1.9 (8) |
O3—Fe2—N3—C16 | −21.1 (3) | C12—N3—C16—C15 | −1.1 (6) |
N4ii—Fe2—N3—C16 | −118.1 (3) | Fe2—N3—C16—C15 | 177.3 (4) |
N4—Fe2—N3—C16 | 61.9 (3) | C12—N3—C16—C17 | 175.6 (4) |
O3ii—Fe2—N3—C12 | −22.8 (4) | Fe2—N3—C16—C17 | −5.9 (4) |
O3—Fe2—N3—C12 | 157.2 (4) | C14—C15—C16—N3 | 0.4 (7) |
N4ii—Fe2—N3—C12 | 60.2 (4) | C14—C15—C16—C17 | −175.8 (4) |
N4—Fe2—N3—C12 | −119.8 (4) | Fe2—O3—C17—O4 | 176.7 (3) |
O3ii—Fe2—N4—C22 | 23.5 (4) | Fe2—O3—C17—C18 | 55.0 (3) |
O3—Fe2—N4—C22 | −156.5 (4) | Fe2—O3—C17—C16 | −56.1 (3) |
N3—Fe2—N4—C22 | 120.4 (4) | N3—C16—C17—O4 | 167.8 (3) |
N3ii—Fe2—N4—C22 | −59.6 (4) | C15—C16—C17—O4 | −15.7 (6) |
O3ii—Fe2—N4—C18 | −156.8 (3) | N3—C16—C17—O3 | 40.6 (4) |
O3—Fe2—N4—C18 | 23.2 (3) | C15—C16—C17—O3 | −142.9 (4) |
N3—Fe2—N4—C18 | −59.9 (3) | N3—C16—C17—C18 | −71.2 (4) |
N3ii—Fe2—N4—C18 | 120.1 (3) | C15—C16—C17—C18 | 105.3 (5) |
C5—N1—C1—C2 | 0.5 (6) | C22—N4—C18—C19 | −0.2 (6) |
Fe1—N1—C1—C2 | 178.4 (3) | Fe2—N4—C18—C19 | −179.9 (3) |
N1—C1—C2—C3 | −0.4 (7) | C22—N4—C18—C17 | −177.5 (3) |
C1—C2—C3—C4 | 0.7 (7) | Fe2—N4—C18—C17 | 2.8 (4) |
C2—C3—C4—C5 | −1.1 (7) | O4—C17—C18—N4 | −162.5 (3) |
C1—N1—C5—C4 | −0.8 (6) | O3—C17—C18—N4 | −37.8 (4) |
Fe1—N1—C5—C4 | −179.1 (3) | C16—C17—C18—N4 | 73.2 (4) |
C1—N1—C5—C6 | −177.6 (3) | O4—C17—C18—C19 | 20.4 (6) |
Fe1—N1—C5—C6 | 4.1 (4) | O3—C17—C18—C19 | 145.1 (4) |
C3—C4—C5—N1 | 1.1 (6) | C16—C17—C18—C19 | −103.9 (5) |
C3—C4—C5—C6 | 177.3 (4) | N4—C18—C19—C20 | 1.0 (7) |
Fe1—O1—C6—O2 | −177.1 (3) | C17—C18—C19—C20 | 177.8 (4) |
Fe1—O1—C6—C7 | −54.6 (3) | C18—C19—C20—C21 | −0.4 (7) |
Fe1—O1—C6—C5 | 55.9 (3) | C19—C20—C21—C22 | −0.9 (7) |
N1—C5—C6—O2 | −165.8 (3) | C18—N4—C22—C21 | −1.1 (6) |
C4—C5—C6—O2 | 17.7 (6) | Fe2—N4—C22—C21 | 178.5 (3) |
N1—C5—C6—O1 | −39.3 (4) | C20—C21—C22—N4 | 1.6 (7) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2o···O3w | 0.85 (1) | 1.86 (1) | 2.708 (5) | 178 (5) |
O4—H4o···O1wiii | 0.85 (1) | 1.77 (1) | 2.614 (5) | 174 (5) |
O1w—H1w1···O1 | 0.85 (1) | 1.84 (2) | 2.676 (4) | 167 (6) |
O1w—H1w2···F1 | 0.85 (1) | 2.03 (1) | 2.881 (9) | 177 (6) |
O1w—H1w2···F2′ | 0.85 (1) | 2.22 (5) | 2.92 (1) | 139 (6) |
O2w—H2w1···O3 | 0.85 (1) | 1.89 (2) | 2.727 (5) | 165 (6) |
O2w—H2w2···F2iii | 0.85 (1) | 2.07 (4) | 2.84 (1) | 150 (6) |
O2w—H2w2···F3′iii | 0.85 (1) | 2.09 (2) | 2.94 (1) | 175 (7) |
O3w—H3w1···F1 | 0.85 (1) | 2.18 (3) | 2.964 (9) | 154 (5) |
O3w—H3w1···F1′ | 0.85 (1) | 2.28 (4) | 3.06 (2) | 153 (7) |
O3w—H3w2···O2w | 0.85 (1) | 1.96 (1) | 2.795 (6) | 171 (6) |
Symmetry code: (iii) x, y−1, z. |