Crystals of the chiral title salt, [Cu(C
20H
22N
4O
2)
2](BF
4)
2·2C
2H
3N, contain Cu(
L2)
22+ cations separated by disordered tetrafluoroborate anions and by acetonitrile solvent molecules. The ligands
L2, (
S,S)-1,2-dimethoxy-1,2-bis(1-methylbenzimidazol-2-yl)ethane, coordinate Cu ions facially to yield a distorted and tetragonally elongated octahedral coordination geometry. Coordination affords V- or butterfly-shaped ligands, cations with the overall shape of the letter X, and seven-membered chelate rings which adopt distorted boat conformations. In the crystal structure, the cations form layers parallel to (001), interspersed with layers containing both tetrafluoroborate anions and acetonitrile molecules. Ligands within a given cation, anions and solvate molecules, and cations and anions, are linked by an extensive C—H
O and C—H
F hydrogen-bonding network. Additionally, cations within a given layer are linked by interionic head-to-tail π–π interactions between two benzimidalole fragments along the
a cell direction and by edge-over-edge C—H
π overlap between the remaining two benzimidazole fragments along the
b cell direction.
Supporting information
CCDC reference: 248743
Key indicators
- Single-crystal X-ray study
- T = 238 K
- Mean (C-C) = 0.012 Å
- Disorder in solvent or counterion
- R factor = 0.051
- wR factor = 0.149
- Data-to-parameter ratio = 9.7
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT111_ALERT_2_B ADDSYM Detects (Pseudo) Centre of Symmetry ..... 98 PerFit
PLAT113_ALERT_2_B ADDSYM Suggests Possible Pseudo/New Spacegroup . P-1
Alert level C
ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
Tmin and Tmax reported: 0.681 1.000
Tmin' and Tmax expected: 0.853 0.979
RR' = 0.782
Please check that your absorption correction is appropriate.
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.78
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98
PLAT216_ALERT_3_C Disordered F24A (An/Solv) ADP max/min Ratio 6.80
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.74 Ratio
PLAT243_ALERT_4_C High Solvent U(eq) as Compared to Neighbors for F21A
PLAT243_ALERT_4_C High Solvent U(eq) as Compared to Neighbors for F22
PLAT243_ALERT_4_C High Solvent U(eq) as Compared to Neighbors for F23
PLAT243_ALERT_4_C High Solvent U(eq) as Compared to Neighbors for F24A
PLAT243_ALERT_4_C High Solvent U(eq) as Compared to Neighbors for F12A
PLAT243_ALERT_4_C High Solvent U(eq) as Compared to Neighbors for F12B
PLAT243_ALERT_4_C High Solvent U(eq) as Compared to Neighbors for F13B
PLAT243_ALERT_4_C High Solvent U(eq) as Compared to Neighbors for F14A
PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors for F24
PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors for B2
PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors for B1
PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors for C1
PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors for C3
PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 30.00 Perc.
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 12
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 25.09
From the CIF: _reflns_number_total 6750
Count of symmetry unique reflns 4268
Completeness (_total/calc) 158.15%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 2482
Fraction of Friedel pairs measured 0.582
Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
21 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
4 ALERT type 3 Indicator that the structure quality may be low
16 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2000); cell refinement: SAINT-Plus (Bruker, 2000); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-32 (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Bruker, 2000).
bis[(
S,
S)-1,2-dimethoxy-1,2-bis(1-methyl-1
H-benzimidazol-2-yl)ethane]copper(II) bis(tetrafluoroborate) acetonitrile disolvate
top
Crystal data top
[Cu(C20H22N4O2)2](BF4)2·2C2H3N | Z = 1 |
Mr = 1020.10 | F(000) = 527 |
Triclinic, P1 | Dx = 1.408 Mg m−3 |
Hall symbol: P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.2286 (5) Å | Cell parameters from 1009 reflections |
b = 11.4896 (6) Å | θ = 2.8–19.9° |
c = 12.0277 (7) Å | µ = 0.54 mm−1 |
α = 80.517 (4)° | T = 238 K |
β = 82.803 (4)° | Block, purple |
γ = 73.690 (4)° | 0.29 × 0.22 × 0.04 mm |
V = 1203.07 (11) Å3 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 6750 independent reflections |
Radiation source: fine-focus sealed tube | 5698 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.039 |
φ and ω scans | θmax = 25.1°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Blessing, 1995) | h = −11→10 |
Tmin = 0.681, Tmax = 1.00 | k = −13→13 |
13054 measured reflections | l = −11→14 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.051 | H-atom parameters constrained |
wR(F2) = 0.149 | w = 1/[σ2(Fo2) + (0.093P)2 + 0.5665P] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max < 0.001 |
6750 reflections | Δρmax = 0.39 e Å−3 |
697 parameters | Δρmin = −0.32 e Å−3 |
23 restraints | Absolute structure: Flack (1983), 2484 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.019 (17) |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Cu | 0.83136 (11) | 0.44447 (8) | 0.99675 (8) | 0.03204 (19) | |
O51 | 0.8173 (5) | 0.4784 (4) | 0.7856 (4) | 0.0417 (12) | |
O53 | 1.1735 (5) | 0.2545 (4) | 0.7231 (4) | 0.0453 (11) | |
O61 | 0.8634 (5) | 0.4445 (4) | 1.1986 (4) | 0.0379 (11) | |
O63 | 0.4662 (5) | 0.5761 (5) | 1.2875 (4) | 0.0538 (13) | |
N11 | 0.4550 (6) | 0.3606 (5) | 1.1925 (5) | 0.0364 (14) | |
N13 | 0.6316 (6) | 0.4117 (5) | 1.0656 (5) | 0.0341 (14) | |
N21 | 0.6577 (8) | 0.7610 (6) | 1.1366 (6) | 0.0480 (16) | |
N23 | 0.7552 (7) | 0.6150 (5) | 1.0289 (5) | 0.0366 (14) | |
N31 | 1.1777 (6) | 0.5328 (5) | 0.7833 (5) | 0.0349 (13) | |
N33 | 1.0242 (7) | 0.4848 (5) | 0.9288 (5) | 0.0373 (14) | |
N41 | 1.0239 (8) | 0.1028 (6) | 0.8831 (6) | 0.0502 (17) | |
N43 | 0.9188 (6) | 0.2690 (5) | 0.9658 (5) | 0.0308 (13) | |
C11 | 0.4408 (8) | 0.3184 (7) | 1.0966 (6) | 0.0386 (17) | |
C12 | 0.5669 (7) | 0.4182 (6) | 1.1695 (5) | 0.0306 (15) | |
C13 | 0.5509 (7) | 0.3502 (6) | 1.0170 (6) | 0.0316 (16) | |
C14 | 0.5600 (8) | 0.3248 (7) | 0.9063 (7) | 0.0427 (18) | |
H14 | 0.6311 | 0.3472 | 0.8512 | 0.051* | |
C15 | 0.4592 (9) | 0.2648 (7) | 0.8816 (7) | 0.0464 (19) | |
H15 | 0.4640 | 0.2463 | 0.8086 | 0.056* | |
C16 | 0.3521 (9) | 0.2318 (7) | 0.9619 (8) | 0.055 (2) | |
H16 | 0.2874 | 0.1911 | 0.9417 | 0.066* | |
C17 | 0.3390 (8) | 0.2573 (7) | 1.0698 (7) | 0.0442 (19) | |
H17 | 0.2662 | 0.2355 | 1.1236 | 0.053* | |
C18 | 0.3603 (8) | 0.3484 (7) | 1.2991 (6) | 0.0500 (19) | |
H18A | 0.2850 | 0.4243 | 1.3063 | 0.075* | |
H18B | 0.4226 | 0.3280 | 1.3614 | 0.075* | |
H18C | 0.3115 | 0.2848 | 1.2992 | 0.075* | |
C21 | 0.6726 (10) | 0.8223 (7) | 1.0273 (7) | 0.050 (2) | |
C22 | 0.7103 (8) | 0.6400 (7) | 1.1308 (7) | 0.0391 (17) | |
C23 | 0.7367 (8) | 0.7301 (6) | 0.9582 (6) | 0.0383 (17) | |
C24 | 0.7770 (9) | 0.7571 (7) | 0.8465 (7) | 0.0472 (19) | |
H24 | 0.8221 | 0.6956 | 0.8018 | 0.057* | |
C25 | 0.7482 (11) | 0.8815 (8) | 0.8007 (8) | 0.066 (3) | |
H25 | 0.7696 | 0.9045 | 0.7239 | 0.079* | |
C26 | 0.6864 (14) | 0.9704 (8) | 0.8735 (8) | 0.084 (3) | |
H26 | 0.6726 | 1.0523 | 0.8432 | 0.101* | |
C27 | 0.6458 (13) | 0.9441 (7) | 0.9848 (8) | 0.073 (3) | |
H27 | 0.6022 | 1.0053 | 1.0301 | 0.088* | |
C28 | 0.5926 (12) | 0.8223 (8) | 1.2362 (8) | 0.076 (3) | |
H28A | 0.6155 | 0.7652 | 1.3035 | 0.114* | |
H28B | 0.4848 | 0.8523 | 1.2338 | 0.114* | |
H28C | 0.6351 | 0.8896 | 1.2363 | 0.114* | |
C31 | 1.2146 (8) | 0.5754 (6) | 0.8747 (7) | 0.0388 (18) | |
C32 | 1.0600 (7) | 0.4807 (6) | 0.8190 (6) | 0.0322 (15) | |
C33 | 1.1169 (8) | 0.5454 (6) | 0.9676 (6) | 0.0354 (17) | |
C34 | 1.1236 (8) | 0.5787 (6) | 1.0731 (6) | 0.0375 (17) | |
H34 | 1.0580 | 0.5611 | 1.1349 | 0.045* | |
C35 | 1.2290 (9) | 0.6376 (7) | 1.0824 (7) | 0.048 (2) | |
H35 | 1.2366 | 0.6591 | 1.1523 | 0.058* | |
C36 | 1.3259 (8) | 0.6667 (7) | 0.9908 (7) | 0.049 (2) | |
H36 | 1.3971 | 0.7067 | 1.0008 | 0.059* | |
C37 | 1.3190 (8) | 0.6373 (7) | 0.8840 (7) | 0.0438 (18) | |
H37 | 1.3821 | 0.6586 | 0.8221 | 0.053* | |
C38 | 1.2574 (8) | 0.5400 (8) | 0.6709 (6) | 0.0483 (18) | |
H38A | 1.3549 | 0.4816 | 0.6721 | 0.072* | |
H38B | 1.2701 | 0.6209 | 0.6485 | 0.072* | |
H38C | 1.1995 | 0.5223 | 0.6179 | 0.072* | |
C41 | 0.9837 (9) | 0.0635 (7) | 0.9927 (8) | 0.049 (2) | |
C42 | 0.9854 (8) | 0.2273 (6) | 0.8688 (6) | 0.0363 (16) | |
C43 | 0.9161 (9) | 0.1685 (7) | 1.0432 (7) | 0.0440 (19) | |
C44 | 0.8579 (9) | 0.1564 (7) | 1.1593 (7) | 0.0451 (18) | |
H44 | 0.8126 | 0.2236 | 1.1971 | 0.054* | |
C45 | 0.8740 (9) | 0.0383 (8) | 1.2106 (8) | 0.059 (2) | |
H45 | 0.8322 | 0.0273 | 1.2848 | 0.071* | |
C46 | 0.9461 (12) | −0.0648 (8) | 1.1623 (9) | 0.073 (3) | |
H46 | 0.9589 | −0.1417 | 1.2050 | 0.087* | |
C47 | 0.9988 (11) | −0.0540 (7) | 1.0515 (8) | 0.064 (2) | |
H47 | 1.0437 | −0.1229 | 1.0159 | 0.077* | |
C48 | 1.0941 (12) | 0.0225 (8) | 0.7937 (8) | 0.075 (3) | |
H48A | 1.2013 | 0.0139 | 0.7837 | 0.113* | |
H48B | 1.0501 | 0.0587 | 0.7237 | 0.113* | |
H48C | 1.0759 | −0.0567 | 0.8164 | 0.113* | |
C51 | 0.9746 (7) | 0.4348 (6) | 0.7499 (5) | 0.0361 (14) | |
H51 | 0.9913 | 0.4699 | 0.6710 | 0.043* | |
C52 | 0.7200 (9) | 0.5290 (8) | 0.6936 (8) | 0.057 (2) | |
H52A | 0.7416 | 0.4726 | 0.6392 | 0.085* | |
H52B | 0.7382 | 0.6052 | 0.6579 | 0.085* | |
H52C | 0.6158 | 0.5425 | 0.7230 | 0.085* | |
C53 | 1.0159 (7) | 0.2965 (6) | 0.7561 (5) | 0.0382 (14) | |
H53 | 0.9595 | 0.2762 | 0.7015 | 0.046* | |
C54 | 1.2109 (11) | 0.2474 (9) | 0.6037 (8) | 0.071 (3) | |
H54A | 1.1533 | 0.3201 | 0.5610 | 0.106* | |
H54B | 1.1872 | 0.1771 | 0.5851 | 0.106* | |
H54C | 1.3171 | 0.2404 | 0.5857 | 0.106* | |
C61 | 0.7319 (7) | 0.5386 (6) | 1.2290 (5) | 0.0354 (13) | |
H61 | 0.7514 | 0.5705 | 1.2948 | 0.042* | |
C62 | 0.9465 (9) | 0.3728 (8) | 1.2904 (7) | 0.052 (2) | |
H62A | 0.8849 | 0.3271 | 1.3386 | 0.078* | |
H62B | 0.9741 | 0.4259 | 1.3330 | 0.078* | |
H62C | 1.0365 | 0.3174 | 1.2612 | 0.078* | |
C63 | 0.5988 (7) | 0.4815 (6) | 1.2622 (6) | 0.0424 (15) | |
H63 | 0.6204 | 0.4216 | 1.3302 | 0.051* | |
C64 | 0.4425 (11) | 0.5881 (10) | 1.4045 (8) | 0.082 (3) | |
H64A | 0.5278 | 0.6079 | 1.4274 | 0.123* | |
H64B | 0.4315 | 0.5124 | 1.4473 | 0.123* | |
H64C | 0.3524 | 0.6522 | 1.4177 | 0.123* | |
B1 | 0.6992 (9) | 0.2281 (7) | 0.5516 (7) | 0.047 (2) | |
F11 | 0.7056 (8) | 0.1937 (6) | 0.4439 (5) | 0.0925 (19) | |
F12A | 0.616 (3) | 0.3438 (13) | 0.5413 (19) | 0.137 (7) | 0.50 |
F12B | 0.5657 (19) | 0.278 (3) | 0.5883 (17) | 0.163 (9) | 0.50 |
F13A | 0.613 (3) | 0.164 (2) | 0.6236 (13) | 0.118 (6) | 0.50 |
F13B | 0.766 (3) | 0.1239 (16) | 0.6159 (14) | 0.141 (7) | 0.50 |
F14A | 0.824 (3) | 0.202 (3) | 0.590 (3) | 0.205 (14) | 0.50 |
F14B | 0.803 (3) | 0.296 (2) | 0.5437 (13) | 0.122 (8) | 0.50 |
B2 | 0.9639 (7) | 0.6536 (5) | 0.4464 (5) | 0.073 (3) | |
F21 | 0.9411 (18) | 0.7083 (11) | 0.5388 (9) | 0.107 (8) | 0.50 |
F22 | 1.008 (2) | 0.5331 (6) | 0.4747 (10) | 0.119 (9) | 0.50 |
F23 | 0.8364 (14) | 0.6845 (17) | 0.3951 (15) | 0.154 (13) | 0.50 |
F24 | 1.0718 (17) | 0.6896 (14) | 0.3764 (12) | 0.159 (10) | 0.50 |
F21A | 0.9727 (18) | 0.7141 (15) | 0.5293 (13) | 0.160 (13) | 0.50 |
F22A | 1.0540 (15) | 0.5401 (8) | 0.4635 (15) | 0.108 (8) | 0.50 |
F23A | 0.8216 (9) | 0.6479 (15) | 0.4461 (14) | 0.107 (6) | 0.50 |
F24A | 1.007 (2) | 0.7096 (17) | 0.3476 (11) | 0.32 (3) | 0.50 |
N1 | 0.4140 (15) | 0.8102 (12) | 0.6143 (11) | 0.133 (5) | |
C1 | 0.4842 (14) | 0.8691 (10) | 0.5744 (10) | 0.081 (3) | |
C2 | 0.5865 (13) | 0.9390 (11) | 0.5110 (12) | 0.092 (3) | |
H2A | 0.5440 | 0.9824 | 0.4423 | 0.137* | |
H2B | 0.6832 | 0.8839 | 0.4932 | 0.137* | |
H2C | 0.5993 | 0.9964 | 0.5562 | 0.137* | |
N3 | 0.2590 (17) | 1.0665 (13) | 0.3434 (11) | 0.137 (5) | |
C3 | 0.1802 (14) | 1.0173 (11) | 0.3990 (11) | 0.084 (3) | |
C4 | 0.0850 (14) | 0.9544 (13) | 0.4705 (12) | 0.104 (4) | |
H4A | −0.0094 | 1.0115 | 0.4897 | 0.155* | |
H4B | 0.1333 | 0.9153 | 0.5382 | 0.155* | |
H4C | 0.0665 | 0.8937 | 0.4321 | 0.155* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu | 0.0349 (3) | 0.0305 (3) | 0.0296 (4) | −0.0093 (2) | 0.0015 (2) | −0.0032 (2) |
O51 | 0.035 (2) | 0.048 (3) | 0.038 (3) | −0.006 (2) | 0.0002 (19) | −0.004 (2) |
O53 | 0.038 (2) | 0.057 (3) | 0.036 (3) | −0.005 (2) | 0.0044 (18) | −0.013 (2) |
O61 | 0.034 (2) | 0.049 (3) | 0.028 (2) | −0.006 (2) | −0.0068 (17) | −0.0027 (19) |
O63 | 0.041 (3) | 0.072 (3) | 0.046 (3) | −0.011 (2) | 0.012 (2) | −0.024 (3) |
N11 | 0.034 (3) | 0.047 (3) | 0.031 (3) | −0.016 (3) | 0.003 (2) | −0.009 (2) |
N13 | 0.032 (3) | 0.037 (3) | 0.033 (4) | −0.012 (3) | 0.000 (3) | −0.003 (3) |
N21 | 0.057 (4) | 0.041 (3) | 0.041 (4) | −0.003 (3) | −0.002 (3) | −0.009 (3) |
N23 | 0.037 (3) | 0.036 (3) | 0.033 (4) | −0.006 (3) | −0.004 (3) | −0.002 (3) |
N31 | 0.037 (3) | 0.031 (3) | 0.032 (3) | −0.005 (2) | −0.004 (2) | 0.004 (2) |
N33 | 0.035 (3) | 0.046 (4) | 0.038 (4) | −0.016 (3) | −0.006 (3) | −0.013 (3) |
N41 | 0.063 (4) | 0.034 (3) | 0.054 (4) | −0.006 (3) | −0.002 (3) | −0.019 (3) |
N43 | 0.031 (3) | 0.028 (3) | 0.033 (4) | −0.007 (2) | −0.004 (2) | −0.001 (3) |
C11 | 0.030 (4) | 0.038 (4) | 0.039 (4) | 0.003 (3) | −0.003 (3) | −0.001 (3) |
C12 | 0.022 (3) | 0.043 (4) | 0.022 (3) | −0.001 (3) | −0.002 (2) | −0.003 (3) |
C13 | 0.032 (4) | 0.030 (3) | 0.029 (4) | −0.006 (3) | −0.001 (3) | 0.003 (3) |
C14 | 0.042 (4) | 0.036 (4) | 0.049 (5) | −0.009 (3) | −0.002 (3) | −0.004 (3) |
C15 | 0.047 (4) | 0.037 (4) | 0.053 (5) | 0.000 (3) | −0.016 (3) | −0.012 (3) |
C16 | 0.047 (4) | 0.044 (4) | 0.079 (7) | −0.014 (4) | −0.017 (4) | −0.013 (4) |
C17 | 0.032 (3) | 0.047 (4) | 0.055 (5) | −0.015 (3) | −0.004 (3) | −0.003 (4) |
C18 | 0.044 (4) | 0.063 (4) | 0.037 (4) | −0.013 (3) | 0.000 (3) | 0.007 (3) |
C21 | 0.062 (5) | 0.041 (4) | 0.046 (5) | −0.005 (4) | −0.008 (4) | −0.014 (4) |
C22 | 0.039 (4) | 0.038 (4) | 0.040 (4) | −0.006 (3) | −0.006 (3) | −0.009 (3) |
C23 | 0.046 (4) | 0.032 (4) | 0.035 (4) | −0.009 (3) | −0.007 (3) | 0.001 (3) |
C24 | 0.069 (5) | 0.037 (4) | 0.031 (4) | −0.006 (3) | −0.007 (3) | −0.005 (3) |
C25 | 0.094 (7) | 0.041 (5) | 0.049 (5) | −0.003 (4) | −0.022 (4) | 0.017 (4) |
C26 | 0.149 (10) | 0.035 (4) | 0.059 (7) | −0.008 (5) | −0.018 (6) | 0.001 (4) |
C27 | 0.119 (8) | 0.035 (4) | 0.054 (6) | 0.002 (4) | −0.004 (5) | −0.015 (4) |
C28 | 0.105 (7) | 0.063 (6) | 0.060 (6) | −0.010 (5) | 0.002 (5) | −0.036 (5) |
C31 | 0.036 (4) | 0.029 (4) | 0.050 (5) | −0.009 (3) | 0.002 (3) | −0.003 (3) |
C32 | 0.036 (4) | 0.032 (3) | 0.028 (4) | −0.009 (3) | −0.004 (3) | 0.000 (3) |
C33 | 0.039 (4) | 0.031 (4) | 0.033 (4) | −0.007 (3) | 0.000 (3) | −0.002 (3) |
C34 | 0.053 (4) | 0.036 (4) | 0.025 (4) | −0.016 (3) | −0.002 (3) | 0.001 (3) |
C35 | 0.055 (5) | 0.039 (4) | 0.056 (5) | −0.010 (4) | −0.022 (4) | −0.012 (4) |
C36 | 0.036 (4) | 0.044 (4) | 0.070 (6) | −0.013 (3) | −0.006 (3) | −0.006 (4) |
C37 | 0.040 (4) | 0.043 (4) | 0.046 (5) | −0.011 (3) | −0.003 (3) | −0.002 (3) |
C38 | 0.042 (4) | 0.069 (5) | 0.036 (4) | −0.022 (4) | 0.006 (3) | −0.005 (3) |
C41 | 0.057 (5) | 0.040 (4) | 0.048 (5) | −0.008 (4) | 0.000 (3) | −0.011 (3) |
C42 | 0.039 (4) | 0.036 (4) | 0.034 (4) | −0.014 (3) | 0.002 (3) | −0.003 (3) |
C43 | 0.045 (4) | 0.040 (4) | 0.050 (5) | −0.011 (4) | −0.006 (4) | −0.013 (4) |
C44 | 0.049 (4) | 0.043 (4) | 0.041 (4) | −0.012 (3) | −0.005 (3) | 0.000 (3) |
C45 | 0.063 (5) | 0.051 (5) | 0.059 (5) | −0.014 (4) | −0.011 (4) | 0.008 (4) |
C46 | 0.100 (7) | 0.039 (5) | 0.071 (7) | −0.012 (5) | −0.016 (5) | 0.009 (4) |
C47 | 0.092 (6) | 0.035 (4) | 0.054 (6) | 0.000 (4) | −0.006 (5) | −0.006 (4) |
C48 | 0.107 (7) | 0.050 (5) | 0.065 (6) | −0.013 (5) | 0.022 (5) | −0.033 (4) |
C51 | 0.034 (3) | 0.048 (4) | 0.025 (3) | −0.012 (3) | 0.005 (2) | −0.006 (3) |
C52 | 0.049 (5) | 0.063 (5) | 0.056 (6) | −0.008 (4) | −0.019 (4) | −0.001 (4) |
C53 | 0.031 (3) | 0.041 (3) | 0.038 (4) | −0.001 (3) | 0.003 (3) | −0.014 (3) |
C54 | 0.068 (5) | 0.081 (6) | 0.057 (5) | −0.010 (4) | 0.016 (4) | −0.028 (4) |
C61 | 0.036 (3) | 0.047 (4) | 0.025 (3) | −0.009 (3) | −0.003 (2) | −0.013 (3) |
C62 | 0.046 (4) | 0.070 (5) | 0.036 (5) | −0.013 (4) | −0.016 (3) | 0.008 (4) |
C63 | 0.037 (4) | 0.050 (4) | 0.038 (4) | −0.011 (3) | 0.000 (3) | −0.001 (3) |
C64 | 0.070 (6) | 0.119 (8) | 0.056 (6) | −0.019 (6) | 0.029 (4) | −0.049 (6) |
B1 | 0.050 (6) | 0.042 (5) | 0.044 (6) | −0.004 (4) | −0.011 (4) | 0.001 (4) |
F11 | 0.127 (5) | 0.116 (5) | 0.048 (4) | −0.054 (4) | −0.006 (3) | −0.014 (3) |
F12A | 0.21 (2) | 0.053 (8) | 0.138 (17) | −0.011 (10) | −0.040 (14) | 0.006 (8) |
F12B | 0.094 (11) | 0.18 (2) | 0.150 (16) | 0.023 (13) | 0.042 (10) | 0.031 (15) |
F13A | 0.184 (18) | 0.129 (13) | 0.074 (10) | −0.103 (14) | 0.025 (10) | −0.026 (9) |
F13B | 0.22 (2) | 0.102 (12) | 0.098 (12) | −0.056 (14) | −0.065 (13) | 0.047 (9) |
F14A | 0.16 (2) | 0.20 (3) | 0.28 (4) | −0.03 (2) | −0.14 (2) | −0.06 (3) |
F14B | 0.177 (18) | 0.181 (17) | 0.069 (9) | −0.148 (16) | 0.020 (10) | −0.034 (10) |
B2 | 0.082 (10) | 0.088 (10) | 0.058 (8) | −0.040 (8) | −0.003 (7) | −0.006 (7) |
F21 | 0.123 (12) | 0.068 (10) | 0.134 (17) | −0.045 (9) | 0.052 (12) | −0.037 (10) |
F22 | 0.29 (3) | 0.049 (8) | 0.031 (7) | −0.076 (12) | −0.033 (10) | 0.019 (5) |
F23 | 0.125 (17) | 0.170 (19) | 0.16 (3) | 0.036 (14) | −0.111 (17) | −0.068 (18) |
F24 | 0.148 (14) | 0.138 (15) | 0.100 (13) | 0.037 (12) | 0.050 (12) | 0.068 (12) |
B2A | 0.082 (10) | 0.088 (10) | 0.058 (8) | −0.040 (8) | −0.003 (7) | −0.006 (7) |
F21A | 0.177 (19) | 0.125 (17) | 0.23 (3) | −0.053 (13) | −0.134 (19) | −0.049 (16) |
F22A | 0.068 (8) | 0.107 (14) | 0.146 (17) | 0.034 (8) | −0.061 (8) | −0.069 (12) |
F23A | 0.091 (10) | 0.170 (18) | 0.056 (10) | −0.011 (10) | −0.011 (7) | −0.041 (10) |
F24A | 0.35 (5) | 0.29 (4) | 0.15 (2) | 0.04 (3) | 0.05 (3) | 0.19 (2) |
N1 | 0.151 (10) | 0.124 (9) | 0.137 (10) | −0.081 (8) | −0.056 (8) | 0.054 (8) |
C1 | 0.091 (8) | 0.056 (6) | 0.090 (8) | −0.014 (6) | −0.029 (6) | 0.011 (5) |
C2 | 0.088 (8) | 0.082 (7) | 0.111 (10) | −0.029 (6) | −0.008 (7) | −0.021 (6) |
N3 | 0.163 (11) | 0.156 (11) | 0.118 (10) | −0.096 (10) | −0.011 (8) | 0.004 (8) |
C3 | 0.097 (8) | 0.075 (7) | 0.089 (8) | −0.032 (7) | −0.028 (7) | −0.007 (6) |
C4 | 0.099 (9) | 0.115 (10) | 0.104 (10) | −0.045 (8) | −0.023 (7) | 0.006 (7) |
Geometric parameters (Å, º) top
Cu—N23 | 1.973 (6) | C34—H34 | 0.9300 |
Cu—N33 | 2.006 (6) | C35—C36 | 1.388 (11) |
Cu—N43 | 2.028 (6) | C35—H35 | 0.9300 |
Cu—N13 | 2.032 (5) | C36—C37 | 1.393 (11) |
Cu—O51 | 2.520 (5) | C36—H36 | 0.9300 |
Cu—O61 | 2.483 (4) | C37—H37 | 0.9300 |
O51—C51 | 1.431 (7) | C38—H38A | 0.9600 |
O51—C52 | 1.453 (9) | C38—H38B | 0.9600 |
O53—C53 | 1.425 (7) | C38—H38C | 0.9600 |
O53—C54 | 1.444 (10) | C41—C43 | 1.392 (11) |
O61—C62 | 1.429 (8) | C41—C47 | 1.396 (12) |
O61—C61 | 1.434 (8) | C42—C53 | 1.491 (9) |
O63—C64 | 1.420 (10) | C43—C44 | 1.431 (11) |
O63—C63 | 1.428 (8) | C44—C45 | 1.371 (11) |
N11—C12 | 1.353 (9) | C44—H44 | 0.9300 |
N11—C11 | 1.357 (10) | C45—C46 | 1.367 (12) |
N11—C18 | 1.468 (9) | C45—H45 | 0.9300 |
N13—C12 | 1.320 (9) | C46—C47 | 1.358 (13) |
N13—C13 | 1.392 (9) | C46—H46 | 0.9300 |
N21—C22 | 1.349 (10) | C47—H47 | 0.9300 |
N21—C21 | 1.395 (11) | C48—H48A | 0.9600 |
N21—C28 | 1.467 (10) | C48—H48B | 0.9600 |
N23—C22 | 1.295 (10) | C48—H48C | 0.9600 |
N23—C23 | 1.428 (9) | C51—C53 | 1.519 (8) |
N31—C32 | 1.373 (9) | C51—H51 | 0.9800 |
N31—C31 | 1.388 (10) | C52—H52A | 0.9600 |
N31—C38 | 1.458 (9) | C52—H52B | 0.9600 |
N33—C32 | 1.325 (9) | C52—H52C | 0.9600 |
N33—C33 | 1.406 (9) | C53—H53 | 0.9800 |
N41—C42 | 1.360 (9) | C54—H54A | 0.9600 |
N41—C41 | 1.362 (11) | C54—H54B | 0.9600 |
N41—C48 | 1.498 (10) | C54—H54C | 0.9600 |
N43—C42 | 1.345 (9) | C61—C63 | 1.531 (8) |
N43—C43 | 1.363 (10) | C61—H61 | 0.9800 |
C11—C13 | 1.389 (10) | C62—H62A | 0.9600 |
C11—C17 | 1.414 (10) | C62—H62B | 0.9600 |
C12—C63 | 1.527 (9) | C62—H62C | 0.9600 |
C13—C14 | 1.397 (11) | C63—H63 | 0.9800 |
C14—C15 | 1.388 (11) | C64—H64A | 0.9600 |
C14—H14 | 0.9300 | C64—H64B | 0.9600 |
C15—C16 | 1.380 (11) | C64—H64C | 0.9600 |
C15—H15 | 0.9300 | B1—F14A | 1.24 (2) |
C16—C17 | 1.360 (11) | B1—F12B | 1.262 (16) |
C16—H16 | 0.9300 | B1—F12A | 1.330 (17) |
C17—H17 | 0.9300 | B1—F13B | 1.346 (17) |
C18—H18A | 0.9600 | B1—F13A | 1.366 (15) |
C18—H18B | 0.9600 | B1—F14B | 1.381 (15) |
C18—H18C | 0.9600 | B1—F11 | 1.404 (10) |
C21—C27 | 1.372 (12) | B2—F22 | 1.327 (6) |
C21—C23 | 1.406 (11) | B2—F23 | 1.329 (6) |
C22—C61 | 1.506 (10) | B2—F21 | 1.331 (6) |
C23—C24 | 1.357 (11) | B2—F24 | 1.334 (6) |
C24—C25 | 1.408 (11) | B2—F22A | 1.334 (6) |
C24—H24 | 0.9300 | B2—F23A | 1.334 (6) |
C25—C26 | 1.406 (12) | B2—F21A | 1.328 (6) |
C25—H25 | 0.9300 | B2—F24A | 1.325 (6) |
C26—C27 | 1.353 (12) | N1—C1 | 1.081 (14) |
C26—H26 | 0.9300 | C1—C2 | 1.471 (16) |
C27—H27 | 0.9300 | C2—H2A | 0.9600 |
C28—H28A | 0.9600 | C2—H2B | 0.9600 |
C28—H28B | 0.9600 | C2—H2C | 0.9600 |
C28—H28C | 0.9600 | N3—C3 | 1.131 (15) |
C31—C37 | 1.373 (10) | C3—C4 | 1.413 (17) |
C31—C33 | 1.406 (10) | C4—H4A | 0.9600 |
C32—C51 | 1.460 (9) | C4—H4B | 0.9600 |
C33—C34 | 1.398 (10) | C4—H4C | 0.9600 |
C34—C35 | 1.355 (11) | | |
| | | |
N23—Cu—N33 | 87.8 (2) | C36—C37—H37 | 121.6 |
N23—Cu—N43 | 177.4 (3) | N31—C38—H38A | 109.5 |
N33—Cu—N43 | 90.3 (2) | N31—C38—H38B | 109.5 |
N23—Cu—N13 | 89.7 (2) | H38A—C38—H38B | 109.5 |
N33—Cu—N13 | 177.4 (3) | N31—C38—H38C | 109.5 |
N43—Cu—N13 | 92.2 (2) | H38A—C38—H38C | 109.5 |
N23—Cu—O61 | 72.4 (2) | H38B—C38—H38C | 109.5 |
N33—Cu—O61 | 98.4 (2) | N41—C41—C43 | 106.2 (7) |
N43—Cu—O61 | 106.24 (19) | N41—C41—C47 | 131.4 (7) |
N13—Cu—O61 | 81.39 (19) | C43—C41—C47 | 122.4 (8) |
N23—Cu—O51 | 99.9 (2) | N43—C42—N41 | 110.2 (6) |
N33—Cu—O51 | 73.9 (2) | N43—C42—C53 | 129.7 (6) |
N43—Cu—O51 | 81.15 (19) | N41—C42—C53 | 120.1 (6) |
N13—Cu—O51 | 106.05 (19) | N43—C43—C41 | 109.2 (7) |
O61—Cu—O51 | 169.55 (15) | N43—C43—C44 | 131.6 (7) |
C51—O51—C52 | 114.5 (5) | C41—C43—C44 | 119.2 (8) |
C51—O51—Cu | 99.7 (3) | C45—C44—C43 | 115.0 (8) |
C52—O51—Cu | 145.6 (4) | C45—C44—H44 | 122.5 |
C53—O53—C54 | 115.1 (6) | C43—C44—H44 | 122.5 |
C62—O61—C61 | 115.7 (5) | C46—C45—C44 | 125.7 (9) |
C62—O61—Cu | 141.7 (4) | C46—C45—H45 | 117.1 |
C61—O61—Cu | 101.3 (3) | C44—C45—H45 | 117.1 |
C64—O63—C63 | 112.2 (6) | C47—C46—C45 | 119.5 (8) |
C12—N11—C11 | 107.4 (6) | C47—C46—H46 | 120.3 |
C12—N11—C18 | 127.6 (6) | C45—C46—H46 | 120.3 |
C11—N11—C18 | 125.0 (6) | C46—C47—C41 | 118.0 (8) |
C12—N13—C13 | 104.5 (5) | C46—C47—H47 | 121.0 |
C12—N13—Cu | 129.8 (5) | C41—C47—H47 | 121.0 |
C13—N13—Cu | 124.4 (4) | N41—C48—H48A | 109.5 |
C22—N21—C21 | 107.5 (6) | N41—C48—H48B | 109.5 |
C22—N21—C28 | 128.4 (7) | H48A—C48—H48B | 109.5 |
C21—N21—C28 | 124.1 (7) | N41—C48—H48C | 109.5 |
C22—N23—C23 | 106.2 (6) | H48A—C48—H48C | 109.5 |
C22—N23—Cu | 121.3 (5) | H48B—C48—H48C | 109.5 |
C23—N23—Cu | 132.5 (5) | O51—C51—C32 | 107.6 (5) |
C32—N31—C31 | 108.4 (6) | O51—C51—C53 | 109.2 (5) |
C32—N31—C38 | 127.4 (6) | C32—C51—C53 | 115.0 (5) |
C31—N31—C38 | 124.2 (6) | O51—C51—H51 | 108.3 |
C32—N33—C33 | 108.5 (6) | C32—C51—H51 | 108.3 |
C32—N33—Cu | 117.9 (5) | C53—C51—H51 | 108.3 |
C33—N33—Cu | 131.8 (5) | O51—C52—H52A | 109.5 |
C42—N41—C41 | 108.0 (6) | O51—C52—H52B | 109.5 |
C42—N41—C48 | 126.3 (7) | H52A—C52—H52B | 109.5 |
C41—N41—C48 | 125.7 (7) | O51—C52—H52C | 109.5 |
C42—N43—C43 | 106.5 (6) | H52A—C52—H52C | 109.5 |
C42—N43—Cu | 128.8 (5) | H52B—C52—H52C | 109.5 |
C43—N43—Cu | 124.7 (5) | O53—C53—C42 | 107.7 (5) |
N11—C11—C13 | 105.9 (6) | O53—C53—C51 | 108.4 (5) |
N11—C11—C17 | 132.2 (7) | C42—C53—C51 | 116.1 (5) |
C13—C11—C17 | 121.8 (7) | O53—C53—H53 | 108.2 |
N13—C12—N11 | 112.7 (6) | C42—C53—H53 | 108.2 |
N13—C12—C63 | 129.5 (6) | C51—C53—H53 | 108.2 |
N11—C12—C63 | 117.8 (6) | O53—C54—H54A | 109.5 |
C11—C13—N13 | 109.4 (6) | O53—C54—H54B | 109.5 |
C11—C13—C14 | 119.8 (7) | H54A—C54—H54B | 109.5 |
N13—C13—C14 | 130.7 (6) | O53—C54—H54C | 109.5 |
C15—C14—C13 | 117.5 (7) | H54A—C54—H54C | 109.5 |
C15—C14—H14 | 121.2 | H54B—C54—H54C | 109.5 |
C13—C14—H14 | 121.2 | O61—C61—C22 | 107.3 (5) |
C16—C15—C14 | 122.1 (8) | O61—C61—C63 | 108.4 (5) |
C16—C15—H15 | 119.0 | C22—C61—C63 | 115.2 (5) |
C14—C15—H15 | 119.0 | O61—C61—H61 | 108.6 |
C17—C16—C15 | 121.6 (7) | C22—C61—H61 | 108.6 |
C17—C16—H16 | 119.2 | C63—C61—H61 | 108.6 |
C15—C16—H16 | 119.2 | O61—C62—H62A | 109.5 |
C16—C17—C11 | 117.1 (7) | O61—C62—H62B | 109.5 |
C16—C17—H17 | 121.4 | H62A—C62—H62B | 109.5 |
C11—C17—H17 | 121.4 | O61—C62—H62C | 109.5 |
N11—C18—H18A | 109.5 | H62A—C62—H62C | 109.5 |
N11—C18—H18B | 109.5 | H62B—C62—H62C | 109.5 |
H18A—C18—H18B | 109.5 | O63—C63—C12 | 108.3 (5) |
N11—C18—H18C | 109.5 | O63—C63—C61 | 108.5 (5) |
H18A—C18—H18C | 109.5 | C12—C63—C61 | 113.4 (5) |
H18B—C18—H18C | 109.5 | O63—C63—H63 | 108.9 |
C27—C21—N21 | 132.7 (8) | C12—C63—H63 | 108.9 |
C27—C21—C23 | 121.6 (8) | C61—C63—H63 | 108.9 |
N21—C21—C23 | 105.5 (7) | O63—C64—H64A | 109.5 |
N23—C22—N21 | 113.3 (7) | O63—C64—H64B | 109.5 |
N23—C22—C61 | 119.9 (6) | H64A—C64—H64B | 109.5 |
N21—C22—C61 | 126.6 (6) | O63—C64—H64C | 109.5 |
C24—C23—C21 | 121.7 (7) | H64A—C64—H64C | 109.5 |
C24—C23—N23 | 130.7 (7) | H64B—C64—H64C | 109.5 |
C21—C23—N23 | 107.4 (7) | F14A—B1—F12A | 119.4 (18) |
C23—C24—C25 | 117.5 (7) | F12B—B1—F13B | 113.9 (15) |
C23—C24—H24 | 121.2 | F14A—B1—F13A | 106 (2) |
C25—C24—H24 | 121.2 | F12A—B1—F13A | 105.3 (15) |
C26—C25—C24 | 118.7 (8) | F12B—B1—F14B | 116.2 (18) |
C26—C25—H25 | 120.7 | F13B—B1—F14B | 102.7 (16) |
C24—C25—H25 | 120.7 | F14A—B1—F11 | 113.8 (16) |
C27—C26—C25 | 124.0 (8) | F12B—B1—F11 | 112.4 (13) |
C27—C26—H26 | 118.0 | F12A—B1—F11 | 104.1 (11) |
C25—C26—H26 | 118.0 | F13B—B1—F11 | 104.4 (10) |
C26—C27—C21 | 116.4 (8) | F13A—B1—F11 | 107.1 (8) |
C26—C27—H27 | 121.8 | F14B—B1—F11 | 106.2 (8) |
C21—C27—H27 | 121.8 | F22—B2—F23 | 110.0 (5) |
N21—C28—H28A | 109.5 | F22—B2—F21 | 109.7 (5) |
N21—C28—H28B | 109.5 | F23—B2—F21 | 109.5 (5) |
H28A—C28—H28B | 109.5 | F22—B2—F24 | 109.1 (5) |
N21—C28—H28C | 109.5 | F23—B2—F24 | 109.3 (5) |
H28A—C28—H28C | 109.5 | F21—B2—F24 | 109.2 (5) |
H28B—C28—H28C | 109.5 | F24A—B2—F21A | 110.2 (5) |
C37—C31—N31 | 132.0 (7) | F24A—B2—F23A | 109.6 (5) |
C37—C31—C33 | 121.7 (7) | F21A—B2—F23A | 109.4 (5) |
N31—C31—C33 | 106.3 (6) | F24A—B2—F22A | 109.4 (5) |
N33—C32—N31 | 109.7 (6) | F21A—B2—F22A | 109.3 (5) |
N33—C32—C51 | 122.5 (6) | F23A—B2—F22A | 109.0 (5) |
N31—C32—C51 | 127.6 (6) | N1—C1—C2 | 173.5 (15) |
C34—C33—C31 | 120.4 (7) | C1—C2—H2A | 109.5 |
C34—C33—N33 | 132.6 (6) | C1—C2—H2B | 109.5 |
C31—C33—N33 | 107.0 (6) | H2A—C2—H2B | 109.5 |
C35—C34—C33 | 117.7 (7) | C1—C2—H2C | 109.5 |
C35—C34—H34 | 121.2 | H2A—C2—H2C | 109.5 |
C33—C34—H34 | 121.2 | H2B—C2—H2C | 109.5 |
C34—C35—C36 | 122.0 (8) | N3—C3—C4 | 178.4 (14) |
C34—C35—H35 | 119.0 | C3—C4—H4A | 109.5 |
C36—C35—H35 | 119.0 | C3—C4—H4B | 109.5 |
C35—C36—C37 | 121.5 (7) | H4A—C4—H4B | 109.5 |
C35—C36—H36 | 119.3 | C3—C4—H4C | 109.5 |
C37—C36—H36 | 119.3 | H4A—C4—H4C | 109.5 |
C31—C37—C36 | 116.8 (7) | H4B—C4—H4C | 109.5 |
C31—C37—H37 | 121.6 | | |
| | | |
N23—Cu—O51—C51 | 117.1 (4) | C43—N43—C42—N41 | 0.4 (8) |
N33—Cu—O51—C51 | 32.3 (4) | Cu—N43—C42—N41 | −178.0 (5) |
N43—Cu—O51—C51 | −60.5 (4) | C43—N43—C42—C53 | 178.9 (7) |
N13—Cu—O51—C51 | −150.3 (3) | Cu—N43—C42—C53 | 0.5 (11) |
O61—Cu—O51—C51 | 75.2 (11) | C41—N41—C42—N43 | −1.2 (9) |
N23—Cu—O51—C52 | −56.7 (8) | C48—N41—C42—N43 | 177.2 (8) |
N33—Cu—O51—C52 | −141.5 (8) | C41—N41—C42—C53 | −179.9 (7) |
N43—Cu—O51—C52 | 125.6 (8) | C48—N41—C42—C53 | −1.4 (12) |
N13—Cu—O51—C52 | 35.8 (8) | C42—N43—C43—C41 | 0.6 (8) |
O61—Cu—O51—C52 | −98.7 (12) | Cu—N43—C43—C41 | 179.0 (5) |
N23—Cu—O61—C62 | −159.8 (7) | C42—N43—C43—C44 | −179.1 (8) |
N33—Cu—O61—C62 | −74.9 (7) | Cu—N43—C43—C44 | −0.6 (12) |
N43—Cu—O61—C62 | 17.9 (7) | N41—C41—C43—N43 | −1.3 (9) |
N13—Cu—O61—C62 | 107.7 (7) | C47—C41—C43—N43 | 179.4 (8) |
O51—Cu—O61—C62 | −116.2 (11) | N41—C41—C43—C44 | 178.4 (7) |
N23—Cu—O61—C61 | 35.2 (3) | C47—C41—C43—C44 | −0.8 (13) |
N33—Cu—O61—C61 | 120.2 (4) | N43—C43—C44—C45 | 179.1 (8) |
N43—Cu—O61—C61 | −147.1 (3) | C41—C43—C44—C45 | −0.6 (11) |
N13—Cu—O61—C61 | −57.2 (3) | C43—C44—C45—C46 | 3.6 (13) |
O51—Cu—O61—C61 | 78.9 (10) | C44—C45—C46—C47 | −5.1 (15) |
N23—Cu—N13—C12 | −61.2 (6) | C45—C46—C47—C41 | 3.2 (15) |
N43—Cu—N13—C12 | 117.2 (6) | N41—C41—C47—C46 | −179.6 (10) |
O61—Cu—N13—C12 | 11.1 (6) | C43—C41—C47—C46 | −0.5 (14) |
O51—Cu—N13—C12 | −161.4 (6) | C52—O51—C51—C32 | 134.0 (6) |
N23—Cu—N13—C13 | 134.4 (6) | Cu—O51—C51—C32 | −42.2 (5) |
N43—Cu—N13—C13 | −47.3 (6) | C52—O51—C51—C53 | −100.6 (6) |
O61—Cu—N13—C13 | −153.4 (6) | Cu—O51—C51—C53 | 83.2 (4) |
O51—Cu—N13—C13 | 34.1 (6) | N33—C32—C51—O51 | 40.1 (8) |
N33—Cu—N23—C22 | −122.7 (6) | N31—C32—C51—O51 | −134.9 (7) |
N13—Cu—N23—C22 | 57.9 (6) | N33—C32—C51—C53 | −81.7 (8) |
O61—Cu—N23—C22 | −23.2 (5) | N31—C32—C51—C53 | 103.2 (8) |
O51—Cu—N23—C22 | 164.1 (6) | C54—O53—C53—C42 | 143.4 (6) |
N33—Cu—N23—C23 | 56.9 (7) | C54—O53—C53—C51 | −90.3 (7) |
N13—Cu—N23—C23 | −122.6 (7) | N43—C42—C53—O53 | 125.7 (7) |
O61—Cu—N23—C23 | 156.4 (7) | N41—C42—C53—O53 | −56.0 (8) |
O51—Cu—N23—C23 | −16.3 (7) | N43—C42—C53—C51 | 4.0 (10) |
N23—Cu—N33—C32 | −115.3 (5) | N41—C42—C53—C51 | −177.6 (6) |
N43—Cu—N33—C32 | 66.3 (5) | O51—C51—C53—O53 | −178.6 (5) |
O61—Cu—N33—C32 | 172.8 (5) | C32—C51—C53—O53 | −57.6 (7) |
O51—Cu—N33—C32 | −14.4 (5) | O51—C51—C53—C42 | −57.3 (7) |
N23—Cu—N33—C33 | 47.3 (7) | C32—C51—C53—C42 | 63.7 (7) |
N43—Cu—N33—C33 | −131.0 (7) | C62—O61—C61—C22 | 150.4 (6) |
O61—Cu—N33—C33 | −24.6 (7) | Cu—O61—C61—C22 | −39.9 (5) |
O51—Cu—N33—C33 | 148.2 (7) | C62—O61—C61—C63 | −84.6 (6) |
N33—Cu—N43—C42 | −50.8 (6) | Cu—O61—C61—C63 | 85.1 (4) |
N13—Cu—N43—C42 | 128.7 (6) | N23—C22—C61—O61 | 29.1 (8) |
O61—Cu—N43—C42 | −149.6 (6) | N21—C22—C61—O61 | −145.2 (7) |
O51—Cu—N43—C42 | 22.8 (6) | N23—C22—C61—C63 | −91.6 (8) |
N33—Cu—N43—C43 | 131.0 (6) | N21—C22—C61—C63 | 94.1 (8) |
N13—Cu—N43—C43 | −49.4 (6) | C64—O63—C63—C12 | 143.5 (6) |
O61—Cu—N43—C43 | 32.3 (6) | C64—O63—C63—C61 | −93.1 (7) |
O51—Cu—N43—C43 | −155.3 (6) | N13—C12—C63—O63 | 116.6 (7) |
C12—N11—C11—C13 | 1.5 (8) | N11—C12—C63—O63 | −62.1 (8) |
C18—N11—C11—C13 | 179.5 (6) | N13—C12—C63—C61 | −3.8 (10) |
C12—N11—C11—C17 | −176.6 (8) | N11—C12—C63—C61 | 177.4 (6) |
C18—N11—C11—C17 | 1.4 (13) | O61—C61—C63—O63 | −177.3 (5) |
C13—N13—C12—N11 | 2.7 (8) | C22—C61—C63—O63 | −57.2 (7) |
Cu—N13—C12—N11 | −164.1 (5) | O61—C61—C63—C12 | −57.0 (7) |
C13—N13—C12—C63 | −176.1 (7) | C22—C61—C63—C12 | 63.2 (7) |
Cu—N13—C12—C63 | 17.1 (10) | F14A—B1—F12A—F12B | −124 (3) |
C11—N11—C12—N13 | −2.7 (8) | F13B—B1—F12A—F12B | −59 (4) |
C18—N11—C12—N13 | 179.3 (6) | F13A—B1—F12A—F12B | −5 (2) |
C11—N11—C12—C63 | 176.2 (6) | F14B—B1—F12A—F12B | −149 (2) |
C18—N11—C12—C63 | −1.7 (10) | F11—B1—F12A—F12B | 108 (2) |
N11—C11—C13—N13 | 0.1 (8) | F14A—B1—F12A—F14B | 25 (2) |
C17—C11—C13—N13 | 178.4 (7) | F12B—B1—F12A—F14B | 149 (2) |
N11—C11—C13—C14 | −176.6 (6) | F13B—B1—F12A—F14B | 90 (3) |
C17—C11—C13—C14 | 1.8 (11) | F13A—B1—F12A—F14B | 144.1 (12) |
C12—N13—C13—C11 | −1.7 (7) | F11—B1—F12A—F14B | −103.4 (9) |
Cu—N13—C13—C11 | 166.1 (5) | F14B—F12A—F12B—B1 | −26.2 (17) |
C12—N13—C13—C14 | 174.5 (7) | B1—F12A—F12B—F13A | 7 (3) |
Cu—N13—C13—C14 | −17.8 (10) | F14B—F12A—F12B—F13A | −19 (5) |
C11—C13—C14—C15 | −1.7 (10) | F14A—B1—F12B—F12A | 92 (3) |
N13—C13—C14—C15 | −177.5 (7) | F13B—B1—F12B—F12A | 152.7 (19) |
C13—C14—C15—C16 | 0.6 (11) | F13A—B1—F12B—F12A | 174 (3) |
C14—C15—C16—C17 | 0.6 (12) | F14B—B1—F12B—F12A | 34 (2) |
C15—C16—C17—C11 | −0.5 (12) | F11—B1—F12B—F12A | −89 (2) |
N11—C11—C17—C16 | 177.2 (8) | F14A—B1—F12B—F13A | −82 (3) |
C13—C11—C17—C16 | −0.6 (11) | F12A—B1—F12B—F13A | −174 (3) |
C22—N21—C21—C27 | −175.7 (11) | F13B—B1—F12B—F13A | −21.6 (18) |
C28—N21—C21—C27 | 5.5 (16) | F14B—B1—F12B—F13A | −140.6 (16) |
C22—N21—C21—C23 | 0.0 (9) | F11—B1—F12B—F13A | 96.8 (12) |
C28—N21—C21—C23 | −178.9 (8) | F12A—F12B—F13A—F13B | 14 (5) |
C23—N23—C22—N21 | 2.2 (9) | B1—F12B—F13A—F13B | 21.4 (17) |
Cu—N23—C22—N21 | −178.1 (5) | F12A—F12B—F13A—B1 | −8 (3) |
C23—N23—C22—C61 | −172.8 (6) | F14A—B1—F13A—F12B | 132 (2) |
Cu—N23—C22—C61 | 6.8 (9) | F12A—B1—F13A—F12B | 4 (2) |
C21—N21—C22—N23 | −1.4 (9) | F13B—B1—F13A—F12B | 157.0 (19) |
C28—N21—C22—N23 | 177.3 (8) | F14B—B1—F13A—F12B | 91 (3) |
C21—N21—C22—C61 | 173.2 (7) | F11—B1—F13A—F12B | −106.1 (16) |
C28—N21—C22—C61 | −8.0 (13) | F14A—B1—F13A—F13B | −25.1 (19) |
C27—C21—C23—C24 | 0.9 (14) | F12B—B1—F13A—F13B | −157.0 (19) |
N21—C21—C23—C24 | −175.4 (8) | F12A—B1—F13A—F13B | −152.6 (16) |
C27—C21—C23—N23 | 177.6 (9) | F14B—B1—F13A—F13B | −66 (3) |
N21—C21—C23—N23 | 1.3 (9) | F11—B1—F13A—F13B | 96.9 (12) |
C22—N23—C23—C24 | 174.1 (8) | F12B—B1—F13B—F14A | −128 (3) |
Cu—N23—C23—C24 | −5.5 (13) | F12A—B1—F13B—F14A | −84 (4) |
C22—N23—C23—C21 | −2.1 (9) | F13A—B1—F13B—F14A | −149 (3) |
Cu—N23—C23—C21 | 178.2 (6) | F14B—B1—F13B—F14A | −2 (3) |
C21—C23—C24—C25 | −1.9 (12) | F11—B1—F13B—F14A | 109 (2) |
N23—C23—C24—C25 | −177.7 (8) | F14A—B1—F13B—F13A | 149 (3) |
C23—C24—C25—C26 | 2.9 (14) | F12B—B1—F13B—F13A | 21.2 (19) |
C24—C25—C26—C27 | −3.2 (18) | F12A—B1—F13B—F13A | 65 (3) |
C25—C26—C27—C21 | 2.1 (19) | F14B—B1—F13B—F13A | 147.7 (12) |
N21—C21—C27—C26 | 174.2 (11) | F11—B1—F13B—F13A | −101.7 (11) |
C23—C21—C27—C26 | −0.9 (16) | F12B—F13A—F13B—F14A | 8 (3) |
C32—N31—C31—C37 | −177.6 (8) | B1—F13A—F13B—F14A | 28 (2) |
C38—N31—C31—C37 | 4.4 (12) | F12B—F13A—F13B—B1 | −20.8 (16) |
C32—N31—C31—C33 | 1.0 (7) | B1—F13B—F14A—F14B | 3 (5) |
C38—N31—C31—C33 | −176.9 (6) | F13A—F13B—F14A—F14B | −26 (7) |
C33—N33—C32—N31 | 2.2 (8) | F13A—F13B—F14A—B1 | −29 (2) |
Cu—N33—C32—N31 | 168.6 (4) | F12B—B1—F14A—F14B | −90 (3) |
C33—N33—C32—C51 | −173.7 (6) | F12A—B1—F14A—F14B | −32 (3) |
Cu—N33—C32—C51 | −7.3 (9) | F13B—B1—F14A—F14B | −178 (3) |
C31—N31—C32—N33 | −2.0 (8) | F13A—B1—F14A—F14B | −150.7 (18) |
C38—N31—C32—N33 | 175.9 (6) | F11—B1—F14A—F14B | 91.7 (17) |
C31—N31—C32—C51 | 173.6 (6) | F12B—B1—F14A—F13B | 88 (3) |
C38—N31—C32—C51 | −8.6 (11) | F12A—B1—F14A—F13B | 146.1 (19) |
C37—C31—C33—C34 | 0.2 (11) | F13A—B1—F14A—F13B | 27 (2) |
N31—C31—C33—C34 | −178.7 (6) | F14B—B1—F14A—F13B | 178 (3) |
C37—C31—C33—N33 | 179.1 (7) | F11—B1—F14A—F13B | −90 (2) |
N31—C31—C33—N33 | 0.3 (7) | F13B—F14A—F14B—B1 | −3 (5) |
C32—N33—C33—C34 | 177.2 (8) | F13B—F14A—F14B—F12A | 20 (6) |
Cu—N33—C33—C34 | 13.4 (12) | B1—F14A—F14B—F12A | 22.5 (18) |
C32—N33—C33—C31 | −1.5 (8) | F12B—B1—F14B—F14A | 127 (3) |
Cu—N33—C33—C31 | −165.3 (5) | F12A—B1—F14B—F14A | 151 (2) |
C31—C33—C34—C35 | −1.5 (11) | F13B—B1—F14B—F14A | 2 (3) |
N33—C33—C34—C35 | 179.9 (8) | F13A—B1—F14B—F14A | 56 (4) |
C33—C34—C35—C36 | 1.2 (12) | F11—B1—F14B—F14A | −108 (2) |
C34—C35—C36—C37 | 0.4 (12) | F14A—B1—F14B—F12A | −151 (2) |
N31—C31—C37—C36 | 179.9 (7) | F12B—B1—F14B—F12A | −24.9 (15) |
C33—C31—C37—C36 | 1.4 (11) | F13B—B1—F14B—F12A | −149.9 (15) |
C35—C36—C37—C31 | −1.7 (11) | F13A—B1—F14B—F12A | −96 (3) |
C42—N41—C41—C43 | 1.5 (9) | F11—B1—F14B—F12A | 100.8 (12) |
C48—N41—C41—C43 | −176.9 (8) | F12B—F12A—F14B—F14A | 4 (3) |
C42—N41—C41—C47 | −179.3 (10) | B1—F12A—F14B—F14A | −25 (2) |
C48—N41—C41—C47 | 2.3 (16) | F12B—F12A—F14B—B1 | 29 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14···O51 | 0.93 | 2.56 | 3.392 (9) | 149 |
C24—H24···O51 | 0.93 | 2.55 | 3.311 (9) | 140 |
C34—H34···O61 | 0.93 | 2.51 | 3.291 (8) | 142 |
C2—H2C···F13Ai | 0.96 | 2.25 | 3.189 (18) | 166 |
C4—H4C···F24ii | 0.96 | 2.53 | 3.45 (3) | 162 |
C4—H4C···F21Aii | 0.96 | 2.52 | 3.16 (3) | 124 |
C28—H28A···F23iii | 0.96 | 2.32 | 3.050 (15) | 132 |
C38—H38C···F22A | 0.96 | 2.37 | 3.303 (17) | 163 |
C46—H46···F24Aiv | 0.93 | 2.20 | 3.098 (15) | 161 |
C51—H51···F22 | 0.98 | 2.35 | 3.323 (13) | 171 |
C51—H51···F22A | 0.98 | 2.54 | 3.516 (19) | 174 |
C52—H52A···F14B | 0.96 | 2.39 | 3.33 (2) | 166 |
C53—H53···F14A | 0.98 | 2.34 | 3.31 (2) | 171 |
C53—H53···F14B | 0.98 | 2.47 | 3.415 (19) | 162 |
C54—H54C···F12Bv | 0.96 | 2.46 | 3.37 (2) | 159 |
C61—H61···F23iii | 0.98 | 2.26 | 3.197 (15) | 159 |
C61—H61···F23Aiii | 0.98 | 2.38 | 3.359 (15) | 175 |
C62—H62A···F14Biii | 0.96 | 2.49 | 3.252 (16) | 137 |
C62—H62B···F22iii | 0.96 | 2.36 | 3.297 (16) | 166 |
C62—H62B···F22Aiii | 0.96 | 2.50 | 3.453 (17) | 172 |
C63—H63···F12Aiii | 0.98 | 2.55 | 3.47 (2) | 157 |
C64—H64B···F12Aiii | 0.96 | 2.42 | 3.12 (2) | 130 |
Symmetry codes: (i) x, y+1, z; (ii) x−1, y, z; (iii) x, y, z+1; (iv) x, y−1, z+1; (v) x+1, y, z. |