Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807056991/sj2416sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807056991/sj2416Isup2.hkl |
CCDC reference: 672653
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.006 Å
- R factor = 0.059
- wR factor = 0.163
- Data-to-parameter ratio = 16.3
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for B1 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for B2 PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 31.00 A 3
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT794_ALERT_5_G Check Predicted Bond Valency for Cu1 (1) 1.26 PLAT794_ALERT_5_G Check Predicted Bond Valency for Fe1 (3) 3.91
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 2 ALERT type 5 Informative message, check
For general background, see: Andres & Schubert (2004); Barigelletti & Flamigni (2000); Licini & Williams (1999). For a functionalized terpyridine complex, see: Hofmeier & Schubert (2004). For 4'-ferrocenyl-2,2':6',2"-terpyridine metal complexes, see: Aguado et al. (2005); Constable et al. (1994); Farlow et al. (1993).
The ligand fctpy was synthesized according to the reported procedure (Farlow et al., 1993). A solution of copper fluoroborate hydrate (69.8 mg, 0.2 mmol), fctpy (82.5 mg, 0.2 mmol) and 2,2'-bipyridine (32.1 g, 0.2 mmol) in methanol (15 ml) was stirred for 4 h. The product was filtered off and dried. The precipitate were recrystallized from acetonitrile (10 ml) to give black block-shaped crystals of the title complex after one week. Yield: 105 mg (65%).
The carbon-bound H atoms were placed at calculated positions (C—H = 0.93 Å) and refined as riding, with U(H) = 1.2Ueq(C).
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXTL (Bruker, 2002).
Fig. 1. The molecular structure of the title complex, with displacement ellipsoids drawn at the 30% probability level, and H atoms as spheres of arbitrary radius. |
[CuFe(C5H5)(C20H14N3)(C10H8N2)](BF4)2 | F(000) = 1636 |
Mr = 810.63 | Dx = 1.596 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 3768 reflections |
a = 14.0780 (8) Å | θ = 2.4–23.2° |
b = 14.2074 (8) Å | µ = 1.14 mm−1 |
c = 16.9442 (10) Å | T = 293 K |
β = 95.488 (1)° | Block, orange |
V = 3373.5 (3) Å3 | 0.20 × 0.18 × 0.10 mm |
Z = 4 |
Bruker APEX area-detector diffractometer | 7656 independent reflections |
Radiation source: fine-focus sealed tube | 5667 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
ϕ and ω scans | θmax = 27.5°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −18→12 |
Tmin = 0.804, Tmax = 0.895 | k = −18→18 |
20780 measured reflections | l = −19→21 |
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)] = 0.059 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.163 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0922P)2 + 0.8536P] where P = (Fo2 + 2Fc2)/3 |
7656 reflections | (Δ/σ)max < 0.001 |
469 parameters | Δρmax = 0.89 e Å−3 |
0 restraints | Δρmin = −0.74 e Å−3 |
[CuFe(C5H5)(C20H14N3)(C10H8N2)](BF4)2 | V = 3373.5 (3) Å3 |
Mr = 810.63 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 14.0780 (8) Å | µ = 1.14 mm−1 |
b = 14.2074 (8) Å | T = 293 K |
c = 16.9442 (10) Å | 0.20 × 0.18 × 0.10 mm |
β = 95.488 (1)° |
Bruker APEX area-detector diffractometer | 7656 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 5667 reflections with I > 2σ(I) |
Tmin = 0.804, Tmax = 0.895 | Rint = 0.033 |
20780 measured reflections |
R[F2 > 2σ(F2)] = 0.059 | 0 restraints |
wR(F2) = 0.163 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.89 e Å−3 |
7656 reflections | Δρmin = −0.74 e Å−3 |
469 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) 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. |
x | y | z | Uiso*/Ueq | ||
Cu1 | −0.10157 (3) | 0.23820 (3) | 0.12009 (3) | 0.03846 (15) | |
Fe1 | 0.38524 (4) | 0.01582 (4) | 0.12953 (3) | 0.03927 (17) | |
N1 | −0.0949 (2) | 0.2164 (2) | 0.00040 (18) | 0.0405 (7) | |
N2 | 0.0094 (2) | 0.1584 (2) | 0.12231 (16) | 0.0364 (6) | |
N3 | −0.0788 (2) | 0.2132 (2) | 0.23883 (18) | 0.0400 (7) | |
N4 | −0.2275 (2) | 0.3013 (2) | 0.11664 (18) | 0.0402 (7) | |
N5 | −0.0599 (2) | 0.3868 (2) | 0.11526 (18) | 0.0398 (7) | |
C1 | −0.1545 (3) | 0.2491 (3) | −0.0600 (2) | 0.0467 (9) | |
H1 | −0.2070 | 0.2846 | −0.0487 | 0.056* | |
C2 | −0.1409 (3) | 0.2319 (3) | −0.1378 (3) | 0.0554 (11) | |
H2 | −0.1840 | 0.2548 | −0.1783 | 0.066* | |
C3 | −0.0634 (4) | 0.1809 (3) | −0.1554 (2) | 0.0555 (11) | |
H3 | −0.0532 | 0.1684 | −0.2078 | 0.067* | |
C4 | −0.0001 (3) | 0.1480 (3) | −0.0937 (2) | 0.0498 (10) | |
H4 | 0.0539 | 0.1143 | −0.1041 | 0.060* | |
C5 | −0.0186 (3) | 0.1662 (2) | −0.0169 (2) | 0.0388 (8) | |
C6 | 0.0418 (3) | 0.1303 (2) | 0.0539 (2) | 0.0388 (8) | |
C7 | 0.1199 (3) | 0.0721 (2) | 0.0536 (2) | 0.0390 (8) | |
H7 | 0.1423 | 0.0543 | 0.0060 | 0.047* | |
C8 | 0.1653 (3) | 0.0398 (2) | 0.1259 (2) | 0.0382 (8) | |
C9 | 0.1277 (3) | 0.0674 (2) | 0.1957 (2) | 0.0387 (8) | |
H9 | 0.1556 | 0.0463 | 0.2445 | 0.046* | |
C10 | 0.0495 (3) | 0.1260 (2) | 0.1922 (2) | 0.0363 (8) | |
C11 | −0.0021 (3) | 0.1583 (2) | 0.2599 (2) | 0.0382 (8) | |
C12 | 0.0236 (3) | 0.1346 (3) | 0.3378 (2) | 0.0456 (9) | |
H12 | 0.0773 | 0.0978 | 0.3514 | 0.055* | |
C13 | −0.0319 (3) | 0.1663 (3) | 0.3955 (2) | 0.0553 (11) | |
H13 | −0.0165 | 0.1504 | 0.4484 | 0.066* | |
C14 | −0.1094 (3) | 0.2212 (3) | 0.3739 (3) | 0.0570 (11) | |
H14 | −0.1475 | 0.2431 | 0.4120 | 0.068* | |
C15 | −0.1309 (3) | 0.2440 (3) | 0.2954 (3) | 0.0513 (10) | |
H15 | −0.1835 | 0.2821 | 0.2812 | 0.062* | |
C16 | 0.2469 (3) | −0.0242 (2) | 0.1279 (2) | 0.0388 (8) | |
C17 | 0.2887 (3) | −0.0628 (2) | 0.0609 (2) | 0.0433 (8) | |
H17 | 0.2680 | −0.0521 | 0.0079 | 0.052* | |
C18 | 0.3666 (3) | −0.1198 (3) | 0.0895 (3) | 0.0477 (9) | |
H18 | 0.4058 | −0.1532 | 0.0583 | 0.057* | |
C19 | 0.3753 (3) | −0.1178 (3) | 0.1735 (3) | 0.0521 (10) | |
H19 | 0.4215 | −0.1488 | 0.2069 | 0.062* | |
C20 | 0.3006 (3) | −0.0597 (3) | 0.1976 (2) | 0.0448 (9) | |
H20 | 0.2889 | −0.0470 | 0.2497 | 0.054* | |
C21 | 0.3866 (4) | 0.1578 (3) | 0.1202 (4) | 0.0723 (14) | |
H21 | 0.3331 | 0.1965 | 0.1139 | 0.087* | |
C22 | 0.4337 (4) | 0.1174 (3) | 0.0592 (3) | 0.0668 (12) | |
H22 | 0.4166 | 0.1242 | 0.0051 | 0.080* | |
C23 | 0.5110 (3) | 0.0651 (3) | 0.0941 (3) | 0.0603 (11) | |
H23 | 0.5546 | 0.0316 | 0.0672 | 0.072* | |
C24 | 0.5112 (3) | 0.0721 (3) | 0.1762 (3) | 0.0637 (12) | |
H24 | 0.5546 | 0.0436 | 0.2136 | 0.076* | |
C25 | 0.4350 (4) | 0.1291 (3) | 0.1926 (3) | 0.0695 (13) | |
H25 | 0.4189 | 0.1454 | 0.2428 | 0.083* | |
C26 | −0.3100 (3) | 0.2553 (3) | 0.1214 (3) | 0.0530 (10) | |
H26 | −0.3088 | 0.1902 | 0.1272 | 0.064* | |
C27 | −0.3961 (3) | 0.3010 (3) | 0.1181 (3) | 0.0605 (12) | |
H27 | −0.4522 | 0.2674 | 0.1219 | 0.073* | |
C28 | −0.3986 (3) | 0.3955 (3) | 0.1091 (3) | 0.0597 (11) | |
H28 | −0.4565 | 0.4274 | 0.1066 | 0.072* | |
C29 | −0.3156 (3) | 0.4440 (3) | 0.1037 (3) | 0.0512 (10) | |
H29 | −0.3167 | 0.5090 | 0.0973 | 0.061* | |
C30 | −0.2305 (3) | 0.3962 (2) | 0.1079 (2) | 0.0370 (8) | |
C31 | −0.1365 (3) | 0.4431 (2) | 0.1060 (2) | 0.0380 (8) | |
C32 | −0.1273 (3) | 0.5395 (3) | 0.0946 (3) | 0.0538 (10) | |
H32 | −0.1810 | 0.5777 | 0.0872 | 0.065* | |
C33 | −0.0376 (4) | 0.5775 (3) | 0.0945 (3) | 0.0632 (12) | |
H33 | −0.0301 | 0.6421 | 0.0886 | 0.076* | |
C34 | 0.0409 (3) | 0.5200 (3) | 0.1030 (3) | 0.0568 (11) | |
H34 | 0.1020 | 0.5444 | 0.1018 | 0.068* | |
C35 | 0.0266 (3) | 0.4249 (3) | 0.1136 (2) | 0.0506 (10) | |
H35 | 0.0796 | 0.3856 | 0.1199 | 0.061* | |
B1 | 0.3098 (4) | 0.4133 (5) | 0.0985 (3) | 0.0656 (15) | |
B2 | 0.7926 (6) | 0.9894 (5) | 0.1737 (4) | 0.0788 (17) | |
F1 | 0.2382 (3) | 0.3522 (3) | 0.0919 (4) | 0.187 (3) | |
F2 | 0.2729 (3) | 0.5017 (2) | 0.1047 (2) | 0.0951 (10) | |
F3 | 0.3600 (4) | 0.4047 (4) | 0.0379 (2) | 0.171 (2) | |
F4 | 0.3677 (3) | 0.3941 (3) | 0.1634 (2) | 0.1181 (14) | |
F5 | 0.7456 (5) | 0.9235 (4) | 0.1292 (4) | 0.183 (2) | |
F6 | 0.7409 (3) | 1.0311 (4) | 0.2257 (2) | 0.156 (2) | |
F7 | 0.8184 (3) | 1.0528 (3) | 0.1205 (2) | 0.1159 (14) | |
F8 | 0.8733 (4) | 0.9568 (4) | 0.2117 (2) | 0.174 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.0358 (3) | 0.0355 (3) | 0.0441 (3) | 0.00386 (18) | 0.00372 (19) | 0.00339 (18) |
Fe1 | 0.0371 (3) | 0.0374 (3) | 0.0441 (3) | 0.0001 (2) | 0.0077 (2) | −0.0013 (2) |
N1 | 0.0397 (17) | 0.0382 (16) | 0.0429 (16) | −0.0047 (14) | 0.0007 (14) | 0.0054 (13) |
N2 | 0.0375 (16) | 0.0342 (15) | 0.0372 (15) | 0.0025 (12) | 0.0028 (12) | 0.0016 (12) |
N3 | 0.0423 (17) | 0.0361 (16) | 0.0423 (16) | 0.0027 (14) | 0.0078 (14) | 0.0012 (12) |
N4 | 0.0338 (16) | 0.0355 (16) | 0.0512 (18) | −0.0028 (13) | 0.0042 (14) | 0.0011 (13) |
N5 | 0.0326 (16) | 0.0387 (16) | 0.0473 (17) | −0.0037 (13) | −0.0001 (13) | 0.0009 (13) |
C1 | 0.041 (2) | 0.046 (2) | 0.051 (2) | −0.0065 (17) | −0.0030 (18) | 0.0115 (17) |
C2 | 0.054 (3) | 0.058 (3) | 0.051 (2) | −0.016 (2) | −0.011 (2) | 0.020 (2) |
C3 | 0.073 (3) | 0.053 (2) | 0.040 (2) | −0.012 (2) | 0.001 (2) | 0.0071 (18) |
C4 | 0.064 (3) | 0.044 (2) | 0.041 (2) | 0.0012 (19) | 0.0055 (19) | 0.0037 (16) |
C5 | 0.044 (2) | 0.0311 (17) | 0.0402 (18) | −0.0035 (15) | −0.0019 (16) | 0.0017 (14) |
C6 | 0.044 (2) | 0.0347 (18) | 0.0382 (18) | −0.0020 (15) | 0.0049 (16) | 0.0024 (14) |
C7 | 0.044 (2) | 0.0346 (18) | 0.0393 (18) | 0.0037 (15) | 0.0106 (16) | 0.0007 (14) |
C8 | 0.038 (2) | 0.0330 (17) | 0.0440 (19) | −0.0044 (15) | 0.0083 (16) | 0.0048 (15) |
C9 | 0.0369 (19) | 0.0389 (19) | 0.0403 (18) | 0.0001 (15) | 0.0033 (15) | 0.0049 (15) |
C10 | 0.040 (2) | 0.0318 (17) | 0.0378 (18) | −0.0022 (15) | 0.0058 (15) | 0.0011 (14) |
C11 | 0.043 (2) | 0.0316 (17) | 0.0414 (19) | −0.0042 (15) | 0.0088 (16) | −0.0003 (14) |
C12 | 0.051 (2) | 0.047 (2) | 0.0389 (19) | −0.0004 (18) | 0.0037 (17) | 0.0033 (16) |
C13 | 0.069 (3) | 0.061 (3) | 0.037 (2) | −0.006 (2) | 0.009 (2) | −0.0006 (18) |
C14 | 0.064 (3) | 0.062 (3) | 0.049 (2) | 0.000 (2) | 0.023 (2) | −0.009 (2) |
C15 | 0.048 (2) | 0.050 (2) | 0.057 (2) | 0.0066 (18) | 0.013 (2) | −0.0089 (18) |
C16 | 0.037 (2) | 0.0329 (18) | 0.048 (2) | 0.0008 (15) | 0.0086 (16) | 0.0038 (15) |
C17 | 0.044 (2) | 0.0376 (19) | 0.048 (2) | −0.0005 (16) | 0.0051 (17) | −0.0039 (16) |
C18 | 0.048 (2) | 0.0355 (19) | 0.062 (2) | 0.0044 (17) | 0.0149 (19) | −0.0024 (17) |
C19 | 0.049 (2) | 0.042 (2) | 0.065 (3) | 0.0098 (18) | 0.010 (2) | 0.0145 (19) |
C20 | 0.042 (2) | 0.044 (2) | 0.049 (2) | 0.0054 (17) | 0.0108 (17) | 0.0120 (17) |
C21 | 0.053 (3) | 0.041 (2) | 0.124 (4) | −0.005 (2) | 0.012 (3) | −0.003 (2) |
C22 | 0.072 (3) | 0.058 (3) | 0.070 (3) | −0.022 (2) | 0.005 (2) | 0.009 (2) |
C23 | 0.052 (3) | 0.058 (3) | 0.074 (3) | −0.015 (2) | 0.022 (2) | −0.008 (2) |
C24 | 0.051 (3) | 0.071 (3) | 0.068 (3) | −0.016 (2) | −0.003 (2) | −0.012 (2) |
C25 | 0.069 (3) | 0.060 (3) | 0.082 (3) | −0.017 (2) | 0.020 (3) | −0.033 (2) |
C26 | 0.044 (2) | 0.042 (2) | 0.074 (3) | −0.0090 (18) | 0.008 (2) | −0.0013 (19) |
C27 | 0.036 (2) | 0.064 (3) | 0.082 (3) | −0.014 (2) | 0.007 (2) | −0.003 (2) |
C28 | 0.034 (2) | 0.070 (3) | 0.075 (3) | 0.006 (2) | 0.002 (2) | −0.006 (2) |
C29 | 0.041 (2) | 0.043 (2) | 0.068 (3) | 0.0054 (18) | 0.001 (2) | 0.0006 (19) |
C30 | 0.0360 (19) | 0.0361 (18) | 0.0386 (18) | −0.0017 (15) | 0.0025 (15) | 0.0027 (14) |
C31 | 0.0361 (19) | 0.0343 (18) | 0.0432 (18) | −0.0001 (15) | 0.0020 (15) | 0.0064 (15) |
C32 | 0.047 (2) | 0.036 (2) | 0.078 (3) | 0.0011 (18) | 0.008 (2) | 0.010 (2) |
C33 | 0.061 (3) | 0.042 (2) | 0.086 (3) | −0.017 (2) | 0.005 (3) | 0.007 (2) |
C34 | 0.045 (3) | 0.058 (3) | 0.067 (3) | −0.018 (2) | 0.005 (2) | 0.005 (2) |
C35 | 0.034 (2) | 0.060 (3) | 0.058 (2) | −0.0026 (18) | 0.0016 (18) | 0.0054 (19) |
B1 | 0.044 (3) | 0.089 (4) | 0.064 (3) | 0.018 (3) | 0.005 (2) | −0.015 (3) |
B2 | 0.084 (4) | 0.090 (4) | 0.064 (3) | 0.015 (3) | 0.016 (3) | 0.011 (3) |
F1 | 0.062 (2) | 0.101 (3) | 0.390 (8) | −0.003 (2) | −0.013 (4) | −0.062 (4) |
F2 | 0.077 (2) | 0.081 (2) | 0.126 (3) | 0.0149 (17) | 0.003 (2) | −0.0155 (19) |
F3 | 0.188 (5) | 0.254 (6) | 0.080 (2) | 0.114 (4) | 0.061 (3) | 0.028 (3) |
F4 | 0.136 (4) | 0.135 (3) | 0.078 (2) | 0.035 (3) | −0.021 (2) | −0.007 (2) |
F5 | 0.226 (6) | 0.130 (4) | 0.192 (5) | −0.100 (4) | 0.013 (4) | −0.006 (3) |
F6 | 0.122 (4) | 0.258 (6) | 0.096 (3) | 0.089 (4) | 0.043 (3) | 0.024 (3) |
F7 | 0.150 (4) | 0.114 (3) | 0.082 (2) | −0.055 (3) | 0.002 (2) | 0.006 (2) |
F8 | 0.177 (5) | 0.263 (6) | 0.085 (3) | 0.149 (4) | 0.026 (3) | 0.029 (3) |
Cu1—N2 | 1.928 (3) | C14—C15 | 1.374 (6) |
Cu1—N4 | 1.983 (3) | C14—H14 | 0.9300 |
Cu1—N3 | 2.038 (3) | C15—H15 | 0.9300 |
Cu1—N1 | 2.062 (3) | C16—C20 | 1.432 (5) |
Cu1—N5 | 2.195 (3) | C16—C17 | 1.436 (5) |
Fe1—C25 | 2.020 (4) | C17—C18 | 1.410 (5) |
Fe1—C21 | 2.023 (5) | C17—H17 | 0.9300 |
Fe1—C16 | 2.026 (4) | C18—C19 | 1.418 (6) |
Fe1—C22 | 2.031 (5) | C18—H18 | 0.9300 |
Fe1—C24 | 2.035 (4) | C19—C20 | 1.427 (5) |
Fe1—C17 | 2.036 (4) | C19—H19 | 0.9300 |
Fe1—C20 | 2.040 (4) | C20—H20 | 0.9300 |
Fe1—C23 | 2.047 (4) | C21—C22 | 1.403 (7) |
Fe1—C19 | 2.049 (4) | C21—C25 | 1.406 (7) |
Fe1—C18 | 2.051 (4) | C21—H21 | 0.9300 |
N1—C1 | 1.342 (5) | C22—C23 | 1.401 (7) |
N1—C5 | 1.346 (5) | C22—H22 | 0.9300 |
N2—C10 | 1.344 (4) | C23—C24 | 1.396 (6) |
N2—C6 | 1.345 (4) | C23—H23 | 0.9300 |
N3—C15 | 1.335 (5) | C24—C25 | 1.393 (7) |
N3—C11 | 1.352 (5) | C24—H24 | 0.9300 |
N4—C26 | 1.342 (5) | C25—H25 | 0.9300 |
N4—C30 | 1.356 (4) | C26—C27 | 1.371 (6) |
N5—C35 | 1.336 (5) | C26—H26 | 0.9300 |
N5—C31 | 1.339 (5) | C27—C28 | 1.350 (6) |
C1—C2 | 1.373 (6) | C27—H27 | 0.9300 |
C1—H1 | 0.9300 | C28—C29 | 1.367 (6) |
C2—C3 | 1.366 (7) | C28—H28 | 0.9300 |
C2—H2 | 0.9300 | C29—C30 | 1.373 (5) |
C3—C4 | 1.389 (6) | C29—H29 | 0.9300 |
C3—H3 | 0.9300 | C30—C31 | 1.484 (5) |
C4—C5 | 1.376 (5) | C31—C32 | 1.392 (5) |
C4—H4 | 0.9300 | C32—C33 | 1.374 (6) |
C5—C6 | 1.493 (5) | C32—H32 | 0.9300 |
C6—C7 | 1.376 (5) | C33—C34 | 1.370 (7) |
C7—C8 | 1.403 (5) | C33—H33 | 0.9300 |
C7—H7 | 0.9300 | C34—C35 | 1.380 (6) |
C8—C9 | 1.397 (5) | C34—H34 | 0.9300 |
C8—C16 | 1.463 (5) | C35—H35 | 0.9300 |
C9—C10 | 1.377 (5) | B1—F3 | 1.306 (6) |
C9—H9 | 0.9300 | B1—F1 | 1.326 (7) |
C10—C11 | 1.487 (5) | B1—F4 | 1.333 (7) |
C11—C12 | 1.377 (5) | B1—F2 | 1.367 (7) |
C12—C13 | 1.385 (6) | B2—F6 | 1.333 (8) |
C12—H12 | 0.9300 | B2—F8 | 1.334 (8) |
C13—C14 | 1.362 (6) | B2—F5 | 1.336 (9) |
C13—H13 | 0.9300 | B2—F7 | 1.348 (7) |
N2—Cu1—N4 | 170.84 (12) | C13—C14—C15 | 119.4 (4) |
N2—Cu1—N3 | 80.08 (12) | C13—C14—H14 | 120.3 |
N4—Cu1—N3 | 99.41 (13) | C15—C14—H14 | 120.3 |
N2—Cu1—N1 | 79.52 (12) | N3—C15—C14 | 122.2 (4) |
N4—Cu1—N1 | 99.40 (13) | N3—C15—H15 | 118.9 |
N3—Cu1—N1 | 157.97 (12) | C14—C15—H15 | 118.9 |
N2—Cu1—N5 | 110.34 (12) | C20—C16—C17 | 107.1 (3) |
N4—Cu1—N5 | 78.78 (12) | C20—C16—C8 | 126.1 (3) |
N3—Cu1—N5 | 100.77 (11) | C17—C16—C8 | 126.8 (3) |
N1—Cu1—N5 | 94.03 (11) | C20—C16—Fe1 | 69.9 (2) |
C25—Fe1—C21 | 40.7 (2) | C17—C16—Fe1 | 69.6 (2) |
C25—Fe1—C16 | 120.98 (18) | C8—C16—Fe1 | 125.3 (2) |
C21—Fe1—C16 | 107.16 (18) | C18—C17—C16 | 108.2 (3) |
C25—Fe1—C22 | 68.0 (2) | C18—C17—Fe1 | 70.4 (2) |
C21—Fe1—C22 | 40.5 (2) | C16—C17—Fe1 | 68.9 (2) |
C16—Fe1—C22 | 124.61 (18) | C18—C17—H17 | 125.9 |
C25—Fe1—C24 | 40.2 (2) | C16—C17—H17 | 125.9 |
C21—Fe1—C24 | 67.9 (2) | Fe1—C17—H17 | 126.3 |
C16—Fe1—C24 | 156.34 (17) | C17—C18—C19 | 108.9 (3) |
C22—Fe1—C24 | 67.7 (2) | C17—C18—Fe1 | 69.2 (2) |
C25—Fe1—C17 | 156.7 (2) | C19—C18—Fe1 | 69.7 (2) |
C21—Fe1—C17 | 120.89 (19) | C17—C18—H18 | 125.6 |
C16—Fe1—C17 | 41.42 (14) | C19—C18—H18 | 125.6 |
C22—Fe1—C17 | 107.37 (18) | Fe1—C18—H18 | 127.1 |
C24—Fe1—C17 | 161.26 (18) | C18—C19—C20 | 107.6 (4) |
C25—Fe1—C20 | 108.12 (19) | C18—C19—Fe1 | 69.8 (2) |
C21—Fe1—C20 | 125.35 (19) | C20—C19—Fe1 | 69.2 (2) |
C16—Fe1—C20 | 41.23 (15) | C18—C19—H19 | 126.2 |
C22—Fe1—C20 | 162.26 (19) | C20—C19—H19 | 126.2 |
C24—Fe1—C20 | 121.37 (19) | Fe1—C19—H19 | 126.3 |
C17—Fe1—C20 | 68.93 (16) | C19—C20—C16 | 108.2 (3) |
C25—Fe1—C23 | 67.49 (19) | C19—C20—Fe1 | 69.9 (2) |
C21—Fe1—C23 | 67.7 (2) | C16—C20—Fe1 | 68.9 (2) |
C16—Fe1—C23 | 161.66 (18) | C19—C20—H20 | 125.9 |
C22—Fe1—C23 | 40.2 (2) | C16—C20—H20 | 125.9 |
C24—Fe1—C23 | 39.99 (18) | Fe1—C20—H20 | 126.9 |
C17—Fe1—C23 | 124.69 (17) | C22—C21—C25 | 107.5 (5) |
C20—Fe1—C23 | 156.05 (18) | C22—C21—Fe1 | 70.0 (3) |
C25—Fe1—C19 | 125.3 (2) | C25—C21—Fe1 | 69.5 (3) |
C21—Fe1—C19 | 162.4 (2) | C22—C21—H21 | 126.2 |
C16—Fe1—C19 | 69.28 (16) | C25—C21—H21 | 126.2 |
C22—Fe1—C19 | 155.5 (2) | Fe1—C21—H21 | 125.8 |
C24—Fe1—C19 | 108.0 (2) | C23—C22—C21 | 108.0 (5) |
C17—Fe1—C19 | 68.55 (17) | C23—C22—Fe1 | 70.5 (3) |
C20—Fe1—C19 | 40.85 (15) | C21—C22—Fe1 | 69.5 (3) |
C23—Fe1—C19 | 120.97 (19) | C23—C22—H22 | 126.0 |
C25—Fe1—C18 | 161.9 (2) | C21—C22—H22 | 126.0 |
C21—Fe1—C18 | 155.8 (2) | Fe1—C22—H22 | 125.6 |
C16—Fe1—C18 | 68.86 (15) | C24—C23—C22 | 108.0 (4) |
C22—Fe1—C18 | 120.87 (19) | C24—C23—Fe1 | 69.5 (3) |
C24—Fe1—C18 | 125.24 (19) | C22—C23—Fe1 | 69.3 (3) |
C17—Fe1—C18 | 40.37 (16) | C24—C23—H23 | 126.0 |
C20—Fe1—C18 | 68.30 (16) | C22—C23—H23 | 126.0 |
C23—Fe1—C18 | 108.13 (18) | Fe1—C23—H23 | 126.8 |
C19—Fe1—C18 | 40.46 (17) | C25—C24—C23 | 108.2 (5) |
C1—N1—C5 | 118.1 (3) | C25—C24—Fe1 | 69.3 (3) |
C1—N1—Cu1 | 127.9 (3) | C23—C24—Fe1 | 70.5 (3) |
C5—N1—Cu1 | 114.0 (2) | C25—C24—H24 | 125.9 |
C10—N2—C6 | 120.6 (3) | C23—C24—H24 | 125.9 |
C10—N2—Cu1 | 119.3 (2) | Fe1—C24—H24 | 125.9 |
C6—N2—Cu1 | 119.9 (2) | C24—C25—C21 | 108.2 (5) |
C15—N3—C11 | 118.6 (3) | C24—C25—Fe1 | 70.5 (2) |
C15—N3—Cu1 | 127.3 (3) | C21—C25—Fe1 | 69.8 (3) |
C11—N3—Cu1 | 114.0 (2) | C24—C25—H25 | 125.9 |
C26—N4—C30 | 118.2 (3) | C21—C25—H25 | 125.9 |
C26—N4—Cu1 | 123.7 (3) | Fe1—C25—H25 | 125.4 |
C30—N4—Cu1 | 118.1 (2) | N4—C26—C27 | 122.2 (4) |
C35—N5—C31 | 118.7 (3) | N4—C26—H26 | 118.9 |
C35—N5—Cu1 | 129.7 (3) | C27—C26—H26 | 118.9 |
C31—N5—Cu1 | 111.3 (2) | C28—C27—C26 | 119.2 (4) |
N1—C1—C2 | 122.5 (4) | C28—C27—H27 | 120.4 |
N1—C1—H1 | 118.8 | C26—C27—H27 | 120.4 |
C2—C1—H1 | 118.8 | C27—C28—C29 | 119.7 (4) |
C3—C2—C1 | 119.4 (4) | C27—C28—H28 | 120.1 |
C3—C2—H2 | 120.3 | C29—C28—H28 | 120.1 |
C1—C2—H2 | 120.3 | C28—C29—C30 | 119.6 (4) |
C2—C3—C4 | 118.9 (4) | C28—C29—H29 | 120.2 |
C2—C3—H3 | 120.6 | C30—C29—H29 | 120.2 |
C4—C3—H3 | 120.6 | N4—C30—C29 | 121.0 (3) |
C5—C4—C3 | 118.9 (4) | N4—C30—C31 | 115.5 (3) |
C5—C4—H4 | 120.6 | C29—C30—C31 | 123.5 (3) |
C3—C4—H4 | 120.6 | N5—C31—C32 | 121.3 (4) |
N1—C5—C4 | 122.2 (3) | N5—C31—C30 | 116.0 (3) |
N1—C5—C6 | 114.3 (3) | C32—C31—C30 | 122.7 (3) |
C4—C5—C6 | 123.5 (4) | C33—C32—C31 | 119.1 (4) |
N2—C6—C7 | 121.2 (3) | C33—C32—H32 | 120.5 |
N2—C6—C5 | 112.2 (3) | C31—C32—H32 | 120.5 |
C7—C6—C5 | 126.6 (3) | C34—C33—C32 | 119.8 (4) |
C6—C7—C8 | 119.4 (3) | C34—C33—H33 | 120.1 |
C6—C7—H7 | 120.3 | C32—C33—H33 | 120.1 |
C8—C7—H7 | 120.3 | C33—C34—C35 | 118.1 (4) |
C9—C8—C7 | 118.0 (3) | C33—C34—H34 | 120.9 |
C9—C8—C16 | 121.0 (3) | C35—C34—H34 | 120.9 |
C7—C8—C16 | 121.0 (3) | N5—C35—C34 | 123.0 (4) |
C10—C9—C8 | 120.0 (3) | N5—C35—H35 | 118.5 |
C10—C9—H9 | 120.0 | C34—C35—H35 | 118.5 |
C8—C9—H9 | 120.0 | F3—B1—F1 | 109.7 (6) |
N2—C10—C9 | 120.7 (3) | F3—B1—F4 | 107.2 (5) |
N2—C10—C11 | 112.2 (3) | F1—B1—F4 | 109.5 (6) |
C9—C10—C11 | 127.0 (3) | F3—B1—F2 | 112.6 (6) |
N3—C11—C12 | 121.6 (3) | F1—B1—F2 | 108.4 (4) |
N3—C11—C10 | 114.3 (3) | F4—B1—F2 | 109.3 (5) |
C12—C11—C10 | 124.0 (4) | F6—B2—F8 | 109.2 (5) |
C11—C12—C13 | 118.8 (4) | F6—B2—F5 | 114.3 (7) |
C11—C12—H12 | 120.6 | F8—B2—F5 | 112.5 (7) |
C13—C12—H12 | 120.6 | F6—B2—F7 | 110.1 (6) |
C14—C13—C12 | 119.3 (4) | F8—B2—F7 | 106.5 (6) |
C14—C13—H13 | 120.4 | F5—B2—F7 | 103.9 (5) |
C12—C13—H13 | 120.4 | ||
N2—Cu1—N1—C1 | 178.9 (3) | C22—Fe1—C19—C18 | −48.1 (6) |
N4—Cu1—N1—C1 | 8.1 (3) | C24—Fe1—C19—C18 | −123.6 (3) |
N3—Cu1—N1—C1 | 156.5 (3) | C17—Fe1—C19—C18 | 36.8 (2) |
N5—Cu1—N1—C1 | −71.2 (3) | C20—Fe1—C19—C18 | 119.0 (4) |
N2—Cu1—N1—C5 | −4.0 (2) | C23—Fe1—C19—C18 | −81.7 (3) |
N4—Cu1—N1—C5 | −174.7 (2) | C25—Fe1—C19—C20 | 76.3 (3) |
N3—Cu1—N1—C5 | −26.3 (5) | C21—Fe1—C19—C20 | 43.7 (7) |
N5—Cu1—N1—C5 | 106.0 (2) | C16—Fe1—C19—C20 | −37.6 (2) |
N3—Cu1—N2—C10 | −0.8 (3) | C22—Fe1—C19—C20 | −167.1 (4) |
N1—Cu1—N2—C10 | −172.5 (3) | C24—Fe1—C19—C20 | 117.4 (3) |
N5—Cu1—N2—C10 | 97.1 (3) | C17—Fe1—C19—C20 | −82.2 (3) |
N3—Cu1—N2—C6 | 174.5 (3) | C23—Fe1—C19—C20 | 159.3 (2) |
N1—Cu1—N2—C6 | 2.8 (3) | C18—Fe1—C19—C20 | −119.0 (4) |
N5—Cu1—N2—C6 | −87.6 (3) | C18—C19—C20—C16 | −1.2 (4) |
N2—Cu1—N3—C15 | −178.5 (3) | Fe1—C19—C20—C16 | 58.3 (3) |
N4—Cu1—N3—C15 | −7.7 (3) | C18—C19—C20—Fe1 | −59.5 (3) |
N1—Cu1—N3—C15 | −156.1 (3) | C17—C16—C20—C19 | 1.0 (4) |
N5—Cu1—N3—C15 | 72.5 (3) | C8—C16—C20—C19 | −178.6 (3) |
N2—Cu1—N3—C11 | 0.9 (2) | Fe1—C16—C20—C19 | −59.0 (3) |
N4—Cu1—N3—C11 | 171.6 (2) | C17—C16—C20—Fe1 | 60.0 (2) |
N1—Cu1—N3—C11 | 23.2 (5) | C8—C16—C20—Fe1 | −119.6 (4) |
N5—Cu1—N3—C11 | −108.1 (2) | C25—Fe1—C20—C19 | −123.4 (3) |
N3—Cu1—N4—C26 | −77.3 (3) | C21—Fe1—C20—C19 | −165.2 (3) |
N1—Cu1—N4—C26 | 91.2 (3) | C16—Fe1—C20—C19 | 119.9 (3) |
N5—Cu1—N4—C26 | −176.6 (3) | C22—Fe1—C20—C19 | 162.3 (6) |
N3—Cu1—N4—C30 | 103.6 (3) | C24—Fe1—C20—C19 | −81.3 (3) |
N1—Cu1—N4—C30 | −87.9 (3) | C17—Fe1—C20—C19 | 81.2 (3) |
N5—Cu1—N4—C30 | 4.4 (3) | C23—Fe1—C20—C19 | −48.3 (5) |
N2—Cu1—N5—C35 | 0.2 (4) | C18—Fe1—C20—C19 | 37.7 (3) |
N4—Cu1—N5—C35 | −178.9 (4) | C25—Fe1—C20—C16 | 116.6 (3) |
N3—Cu1—N5—C35 | 83.5 (3) | C21—Fe1—C20—C16 | 74.9 (3) |
N1—Cu1—N5—C35 | −80.1 (3) | C22—Fe1—C20—C16 | 42.4 (7) |
N2—Cu1—N5—C31 | 174.1 (2) | C24—Fe1—C20—C16 | 158.7 (2) |
N4—Cu1—N5—C31 | −5.0 (2) | C17—Fe1—C20—C16 | −38.8 (2) |
N3—Cu1—N5—C31 | −102.6 (3) | C23—Fe1—C20—C16 | −168.2 (4) |
N1—Cu1—N5—C31 | 93.8 (3) | C19—Fe1—C20—C16 | −119.9 (3) |
C5—N1—C1—C2 | 1.0 (5) | C18—Fe1—C20—C16 | −82.3 (2) |
Cu1—N1—C1—C2 | 178.0 (3) | C25—Fe1—C21—C22 | 118.5 (4) |
N1—C1—C2—C3 | −0.9 (6) | C16—Fe1—C21—C22 | −123.6 (3) |
C1—C2—C3—C4 | −0.2 (6) | C24—Fe1—C21—C22 | 81.0 (3) |
C2—C3—C4—C5 | 1.3 (6) | C17—Fe1—C21—C22 | −80.5 (3) |
C1—N1—C5—C4 | 0.2 (5) | C20—Fe1—C21—C22 | −165.4 (3) |
Cu1—N1—C5—C4 | −177.2 (3) | C23—Fe1—C21—C22 | 37.6 (3) |
C1—N1—C5—C6 | −178.2 (3) | C19—Fe1—C21—C22 | 160.9 (6) |
Cu1—N1—C5—C6 | 4.4 (4) | C18—Fe1—C21—C22 | −47.1 (6) |
C3—C4—C5—N1 | −1.4 (6) | C16—Fe1—C21—C25 | 117.8 (3) |
C3—C4—C5—C6 | 176.9 (4) | C22—Fe1—C21—C25 | −118.5 (4) |
C10—N2—C6—C7 | −3.6 (5) | C24—Fe1—C21—C25 | −37.5 (3) |
Cu1—N2—C6—C7 | −178.9 (3) | C17—Fe1—C21—C25 | 161.0 (3) |
C10—N2—C6—C5 | 173.9 (3) | C20—Fe1—C21—C25 | 76.1 (3) |
Cu1—N2—C6—C5 | −1.3 (4) | C23—Fe1—C21—C25 | −80.9 (3) |
N1—C5—C6—N2 | −2.2 (4) | C19—Fe1—C21—C25 | 42.4 (8) |
C4—C5—C6—N2 | 179.5 (3) | C18—Fe1—C21—C25 | −165.7 (4) |
N1—C5—C6—C7 | 175.2 (3) | C25—C21—C22—C23 | −0.6 (5) |
C4—C5—C6—C7 | −3.1 (6) | Fe1—C21—C22—C23 | −60.3 (3) |
N2—C6—C7—C8 | 1.4 (5) | C25—C21—C22—Fe1 | 59.7 (3) |
C5—C6—C7—C8 | −175.8 (3) | C25—Fe1—C22—C23 | 80.7 (3) |
C6—C7—C8—C9 | 1.0 (5) | C21—Fe1—C22—C23 | 118.9 (4) |
C6—C7—C8—C16 | 178.4 (3) | C16—Fe1—C22—C23 | −166.0 (3) |
C7—C8—C9—C10 | −1.1 (5) | C24—Fe1—C22—C23 | 37.1 (3) |
C16—C8—C9—C10 | −178.5 (3) | C17—Fe1—C22—C23 | −123.6 (3) |
C6—N2—C10—C9 | 3.5 (5) | C20—Fe1—C22—C23 | 161.4 (5) |
Cu1—N2—C10—C9 | 178.8 (3) | C19—Fe1—C22—C23 | −47.4 (6) |
C6—N2—C10—C11 | −174.7 (3) | C18—Fe1—C22—C23 | −81.6 (3) |
Cu1—N2—C10—C11 | 0.6 (4) | C25—Fe1—C22—C21 | −38.2 (3) |
C8—C9—C10—N2 | −1.1 (5) | C16—Fe1—C22—C21 | 75.2 (3) |
C8—C9—C10—C11 | 176.8 (3) | C24—Fe1—C22—C21 | −81.7 (3) |
C15—N3—C11—C12 | −0.6 (5) | C17—Fe1—C22—C21 | 117.5 (3) |
Cu1—N3—C11—C12 | 180.0 (3) | C20—Fe1—C22—C21 | 42.5 (7) |
C15—N3—C11—C10 | 178.6 (3) | C23—Fe1—C22—C21 | −118.9 (4) |
Cu1—N3—C11—C10 | −0.8 (4) | C19—Fe1—C22—C21 | −166.2 (4) |
N2—C10—C11—N3 | 0.2 (4) | C18—Fe1—C22—C21 | 159.5 (3) |
C9—C10—C11—N3 | −177.8 (3) | C21—C22—C23—C24 | 0.7 (5) |
N2—C10—C11—C12 | 179.4 (3) | Fe1—C22—C23—C24 | −58.9 (3) |
C9—C10—C11—C12 | 1.3 (6) | C21—C22—C23—Fe1 | 59.6 (3) |
N3—C11—C12—C13 | 1.3 (6) | C25—Fe1—C23—C24 | 37.6 (3) |
C10—C11—C12—C13 | −177.8 (3) | C21—Fe1—C23—C24 | 81.7 (3) |
C11—C12—C13—C14 | −1.0 (6) | C16—Fe1—C23—C24 | 158.9 (5) |
C12—C13—C14—C15 | 0.0 (7) | C22—Fe1—C23—C24 | 119.6 (4) |
C11—N3—C15—C14 | −0.4 (6) | C17—Fe1—C23—C24 | −165.2 (3) |
Cu1—N3—C15—C14 | 178.9 (3) | C20—Fe1—C23—C24 | −46.5 (5) |
C13—C14—C15—N3 | 0.8 (7) | C19—Fe1—C23—C24 | −81.2 (3) |
C9—C8—C16—C20 | −4.6 (6) | C18—Fe1—C23—C24 | −123.7 (3) |
C7—C8—C16—C20 | 178.1 (3) | C25—Fe1—C23—C22 | −82.1 (3) |
C9—C8—C16—C17 | 175.8 (3) | C21—Fe1—C23—C22 | −37.9 (3) |
C7—C8—C16—C17 | −1.5 (6) | C16—Fe1—C23—C22 | 39.3 (7) |
C9—C8—C16—Fe1 | −94.4 (4) | C24—Fe1—C23—C22 | −119.6 (4) |
C7—C8—C16—Fe1 | 88.3 (4) | C17—Fe1—C23—C22 | 75.1 (3) |
C25—Fe1—C16—C20 | −82.3 (3) | C20—Fe1—C23—C22 | −166.1 (4) |
C21—Fe1—C16—C20 | −124.5 (3) | C19—Fe1—C23—C22 | 159.2 (3) |
C22—Fe1—C16—C20 | −165.6 (3) | C18—Fe1—C23—C22 | 116.7 (3) |
C24—Fe1—C16—C20 | −50.5 (5) | C22—C23—C24—C25 | −0.5 (5) |
C17—Fe1—C16—C20 | 118.0 (3) | Fe1—C23—C24—C25 | −59.3 (3) |
C23—Fe1—C16—C20 | 164.7 (5) | C22—C23—C24—Fe1 | 58.8 (3) |
C19—Fe1—C16—C20 | 37.3 (2) | C21—Fe1—C24—C25 | 38.0 (3) |
C18—Fe1—C16—C20 | 80.8 (2) | C16—Fe1—C24—C25 | −44.4 (6) |
C25—Fe1—C16—C17 | 159.8 (3) | C22—Fe1—C24—C25 | 81.9 (4) |
C21—Fe1—C16—C17 | 117.5 (3) | C17—Fe1—C24—C25 | 159.9 (5) |
C22—Fe1—C16—C17 | 76.5 (3) | C20—Fe1—C24—C25 | −80.9 (4) |
C24—Fe1—C16—C17 | −168.5 (4) | C23—Fe1—C24—C25 | 119.2 (5) |
C20—Fe1—C16—C17 | −118.0 (3) | C19—Fe1—C24—C25 | −123.8 (3) |
C23—Fe1—C16—C17 | 46.7 (6) | C18—Fe1—C24—C25 | −165.2 (3) |
C19—Fe1—C16—C17 | −80.7 (2) | C25—Fe1—C24—C23 | −119.2 (5) |
C18—Fe1—C16—C17 | −37.2 (2) | C21—Fe1—C24—C23 | −81.2 (3) |
C25—Fe1—C16—C8 | 38.4 (4) | C16—Fe1—C24—C23 | −163.6 (4) |
C21—Fe1—C16—C8 | −3.8 (4) | C22—Fe1—C24—C23 | −37.3 (3) |
C22—Fe1—C16—C8 | −44.9 (4) | C17—Fe1—C24—C23 | 40.7 (7) |
C24—Fe1—C16—C8 | 70.2 (6) | C20—Fe1—C24—C23 | 159.8 (3) |
C17—Fe1—C16—C8 | −121.3 (4) | C19—Fe1—C24—C23 | 117.0 (3) |
C20—Fe1—C16—C8 | 120.7 (4) | C18—Fe1—C24—C23 | 75.6 (3) |
C23—Fe1—C16—C8 | −74.6 (6) | C23—C24—C25—C21 | 0.2 (5) |
C19—Fe1—C16—C8 | 158.0 (4) | Fe1—C24—C25—C21 | −59.8 (3) |
C18—Fe1—C16—C8 | −158.5 (4) | C23—C24—C25—Fe1 | 60.0 (3) |
C20—C16—C17—C18 | −0.5 (4) | C22—C21—C25—C24 | 0.3 (5) |
C8—C16—C17—C18 | 179.2 (3) | Fe1—C21—C25—C24 | 60.3 (3) |
Fe1—C16—C17—C18 | 59.7 (3) | C22—C21—C25—Fe1 | −60.0 (3) |
C20—C16—C17—Fe1 | −60.2 (3) | C21—Fe1—C25—C24 | −118.9 (5) |
C8—C16—C17—Fe1 | 119.5 (4) | C16—Fe1—C25—C24 | 160.9 (3) |
C25—Fe1—C17—C18 | −167.9 (5) | C22—Fe1—C25—C24 | −81.0 (3) |
C21—Fe1—C17—C18 | 159.7 (3) | C17—Fe1—C25—C24 | −163.8 (4) |
C16—Fe1—C17—C18 | −119.5 (3) | C20—Fe1—C25—C24 | 117.5 (3) |
C22—Fe1—C17—C18 | 117.5 (3) | C23—Fe1—C25—C24 | −37.4 (3) |
C24—Fe1—C17—C18 | 46.1 (6) | C19—Fe1—C25—C24 | 75.5 (4) |
C20—Fe1—C17—C18 | −80.9 (2) | C18—Fe1—C25—C24 | 42.0 (7) |
C23—Fe1—C17—C18 | 76.7 (3) | C16—Fe1—C25—C21 | −80.2 (3) |
C19—Fe1—C17—C18 | −36.9 (2) | C22—Fe1—C25—C21 | 38.0 (3) |
C25—Fe1—C17—C16 | −48.4 (6) | C24—Fe1—C25—C21 | 118.9 (5) |
C21—Fe1—C17—C16 | −80.9 (3) | C17—Fe1—C25—C21 | −44.9 (6) |
C22—Fe1—C17—C16 | −123.0 (2) | C20—Fe1—C25—C21 | −123.6 (3) |
C24—Fe1—C17—C16 | 165.5 (5) | C23—Fe1—C25—C21 | 81.5 (3) |
C20—Fe1—C17—C16 | 38.6 (2) | C19—Fe1—C25—C21 | −165.6 (3) |
C23—Fe1—C17—C16 | −163.8 (2) | C18—Fe1—C25—C21 | 161.0 (5) |
C19—Fe1—C17—C16 | 82.6 (2) | C30—N4—C26—C27 | −0.3 (6) |
C18—Fe1—C17—C16 | 119.5 (3) | Cu1—N4—C26—C27 | −179.3 (3) |
C16—C17—C18—C19 | −0.3 (4) | N4—C26—C27—C28 | 0.4 (7) |
Fe1—C17—C18—C19 | 58.5 (3) | C26—C27—C28—C29 | −0.1 (7) |
C16—C17—C18—Fe1 | −58.8 (2) | C27—C28—C29—C30 | −0.3 (7) |
C25—Fe1—C18—C17 | 164.5 (6) | C26—N4—C30—C29 | −0.2 (5) |
C21—Fe1—C18—C17 | −46.8 (5) | Cu1—N4—C30—C29 | 178.9 (3) |
C16—Fe1—C18—C17 | 38.1 (2) | C26—N4—C30—C31 | 177.8 (3) |
C22—Fe1—C18—C17 | −80.4 (3) | Cu1—N4—C30—C31 | −3.1 (4) |
C24—Fe1—C18—C17 | −163.5 (3) | C28—C29—C30—N4 | 0.5 (6) |
C20—Fe1—C18—C17 | 82.6 (2) | C28—C29—C30—C31 | −177.3 (4) |
C23—Fe1—C18—C17 | −122.6 (3) | C35—N5—C31—C32 | 0.2 (6) |
C19—Fe1—C18—C17 | 120.6 (3) | Cu1—N5—C31—C32 | −174.4 (3) |
C25—Fe1—C18—C19 | 43.9 (7) | C35—N5—C31—C30 | 179.6 (3) |
C21—Fe1—C18—C19 | −167.4 (4) | Cu1—N5—C31—C30 | 4.9 (4) |
C16—Fe1—C18—C19 | −82.5 (3) | N4—C30—C31—N5 | −1.6 (5) |
C22—Fe1—C18—C19 | 159.0 (3) | C29—C30—C31—N5 | 176.3 (4) |
C24—Fe1—C18—C19 | 75.9 (3) | N4—C30—C31—C32 | 177.7 (4) |
C17—Fe1—C18—C19 | −120.6 (3) | C29—C30—C31—C32 | −4.4 (6) |
C20—Fe1—C18—C19 | −38.0 (2) | N5—C31—C32—C33 | −1.3 (6) |
C23—Fe1—C18—C19 | 116.8 (3) | C30—C31—C32—C33 | 179.4 (4) |
C17—C18—C19—C20 | 0.9 (4) | C31—C32—C33—C34 | 2.0 (7) |
Fe1—C18—C19—C20 | 59.1 (3) | C32—C33—C34—C35 | −1.6 (7) |
C17—C18—C19—Fe1 | −58.3 (3) | C31—N5—C35—C34 | 0.2 (6) |
C25—Fe1—C19—C18 | −164.7 (3) | Cu1—N5—C35—C34 | 173.7 (3) |
C21—Fe1—C19—C18 | 162.7 (6) | C33—C34—C35—N5 | 0.5 (7) |
C16—Fe1—C19—C18 | 81.3 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···F4i | 0.93 | 2.51 | 3.306 (5) | 143 |
C4—H4···F8ii | 0.93 | 2.40 | 3.176 (6) | 141 |
C17—H17···F7ii | 0.93 | 2.39 | 3.296 (5) | 165 |
C13—H13···F3iii | 0.93 | 2.54 | 3.140 (6) | 123 |
C34—H34···F2 | 0.93 | 2.48 | 3.274 (6) | 144 |
C35—H35···F1 | 0.93 | 2.37 | 3.208 (6) | 149 |
Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) −x+1, −y+1, −z; (iii) x−1/2, −y+1/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [CuFe(C5H5)(C20H14N3)(C10H8N2)](BF4)2 |
Mr | 810.63 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 14.0780 (8), 14.2074 (8), 16.9442 (10) |
β (°) | 95.488 (1) |
V (Å3) | 3373.5 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.14 |
Crystal size (mm) | 0.20 × 0.18 × 0.10 |
Data collection | |
Diffractometer | Bruker APEX area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.804, 0.895 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 20780, 7656, 5667 |
Rint | 0.033 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.059, 0.163, 1.05 |
No. of reflections | 7656 |
No. of parameters | 469 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.89, −0.74 |
Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2002).
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···F4i | 0.93 | 2.51 | 3.306 (5) | 143.1 |
C4—H4···F8ii | 0.93 | 2.40 | 3.176 (6) | 141.1 |
C17—H17···F7ii | 0.93 | 2.39 | 3.296 (5) | 164.6 |
C13—H13···F3iii | 0.93 | 2.54 | 3.140 (6) | 122.8 |
C34—H34···F2 | 0.93 | 2.48 | 3.274 (6) | 143.9 |
C35—H35···F1 | 0.93 | 2.37 | 3.208 (6) | 149.0 |
Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) −x+1, −y+1, −z; (iii) x−1/2, −y+1/2, z+1/2. |
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The chemistry of 2,2':6',2"-terpyridine (tpy) ligand has been the subject of numerous studies because of its good chelating ability towards transition metal ions, and some of its complexes are promising materials for potential applications as luminescent devices (Andres & Schubert, 2004; Barigelletti & Flamigni, 2000; Licini & Williams, 1999). Especially, the central pyridyl ring can be easily functionalized to attain different aims, and much work has been done on functionalized terpyridine complexes (Hofmeier & and Schubert, 2004). For example, several studies have been carried out on the structure and electrochemical properties of 4'-ferrocenyl-2,2':6',2"-terpyridine (fctpy) and its AuI, RuII, CoII and FeII complexes (Aguado et al., 2005; Constable et al., 1994; Farlow et al., 1993). In this work, we represent a new mixed-ligand complex, incorporating fctpy and 2,2'-bipyridine (bpy) ligands.
In the title complex, (I), Fig. 1, the CuII atom is five-coordinated by three N atoms from the fctpy ligand and two N atoms from the bpy, ligand displaying a distorted square pyramidal geometry. The apex of the pyramid is occupied by the N5 from the bpy ligand with a Cu1—N5 distance of 2.195 (3) Å, which is somewhat longer than those in the basal plane [Cu—N distances in the range 1.928 (3)–2.062 (3) Å]. The angles subtended at Cu(1) by the tridentate terpyridyl ligand are 79.52 (12) and 80.08 (12) ° respectively. The two cyclopentadienyl rings of the ferrocenyl group are almost eclipsed and the dihedral angle between the two rings is 5.1 (2) °.
In the crystal structure, tetrafluoridoborate counterions are involved as acceptors in intermolecular C—H···F hydrogen-bonding interactions with both the bipyridyl and terpyridyl ligands, resulting a three-dimensional supramolecular structure, Table 1.