A chiral facially coordinated CuII complex derived from a tridentate bis­(benz­imidazole) ligand: bis­[(S,S)-1,2-di­methoxy-1,2-bis(1-methylbenzimidazol-2-yl)­ethane]copper(II) bis­(tetra­fluoro­borate) aceto­nitrile disolvate

Stibrany, R.T.; Schugar, H.J.; Potenza, J.A.

doi:10.1107/S1600536804017295

A chiral facially coordinated Cu^II complex derived from a tridentate bis(benzimidazole) ligand: bis[(S,S)-1,2-dimethoxy-1,2-bis(1-methylbenzimidazol-2-yl)ethane]copper(II) bis(tetrafluoroborate) acetonitrile disolvate

R. T. Stibrany, H. J. Schugar and J. A. Potenza

Crystals of the chiral title salt, [Cu(C₂₀H₂₂N₄O₂)₂](BF₄)₂·2C₂H₃N, 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.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804017295/lh6241sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536804017295/lh6241Isup2.hkl Contains datablock I

CCDC reference: 248743

checkCIF report

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

Computing details top

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-1H-benzimidazol-2-yl)ethane]copper(II) bis(tetrafluoroborate) acetonitrile disolvate top

Crystal data top

[Cu(C₂₀H₂₂N₄O₂)₂](BF₄)₂·2C₂H₃N	Z = 1
M_r = 1020.10	F(000) = 527
Triclinic, P1	D_x = 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	R_int = 0.039
φ and ω scans	θ_max = 25.1°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Blessing, 1995)	h = −11→10
T_min = 0.681, T_max = 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(F_o²) + (0.093P)² + 0.5665P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
6750 reflections	Δρ_max = 0.39 e Å⁻³
697 parameters	Δρ_min = −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	U_iso*/U_eq	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···F24A^iv	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···F12B^v	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.

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Format		BIBTeX
		EndNote
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		Refer
		Medline
		CIF
		SGML
		Text
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A chiral facially coordinated CuII complex derived from a tridentate bis­(benz­imidazole) ligand: bis­[(S,S)-1,2-di­methoxy-1,2-bis(1-methylbenzimidazol-2-yl)­ethane]copper(II) bis­(tetra­fluoro­borate) aceto­nitrile disolvate

Supporting information

Key indicators

checkCIF/PLATON results

A chiral facially coordinated Cu^II complex derived from a tridentate bis(benzimidazole) ligand: bis[(S,S)-1,2-dimethoxy-1,2-bis(1-methylbenzimidazol-2-yl)ethane]copper(II) bis(tetrafluoroborate) acetonitrile disolvate