Bis(2,9-dimethyl-1,10-phenanthroline)copper(I) tetra­phenyl­borate dichloro­methane solvate

In the title compound, [Cu(C₁₄H₁₂N₂)₂]C₂₄H₂₀B·CH₂Cl₂, Cu^I is chelated by two 2,9-dimethyl-1,10-phenanthroline (2,9-Me₂phen) ligands, in a distorted tetra­hedral coordination geometry. The average Cu—N bond length is 2.032 Å, and the inter­ligand dihedral angle is 77.60 (6)°. The complexes form π–π stacking inter­actions between 2,9-Me₂phen ligands, with a perpendicular inter­planar separation of 3.652 (5) Å.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.047
• wR factor = 0.148
• Data-to-parameter ratio = 24.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.99
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000)         100 Deg.
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          3
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C35    -   C40     ..       5.74 su
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C55

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: ORTEP-3 for Windows (Farrugia, 1997).

Bis(2,9-dimethyl-1,10-phenanthroline)copper(I) tetraphenylborate dichloromethane solvate

Crystal data

[Cu(C14H12N2)2]C24H20B·CH2Cl2	Z = 2
Mr = 884.19	F(000) = 920
Triclinic, P1	Dx = 1.299 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.9766 (4) Å	Cell parameters from 6411 reflections
b = 13.1942 (4) Å	θ = 2.3–25.5°
c = 15.1181 (5) Å	µ = 0.64 mm^−1
α = 78.836 (1)°	T = 296 K
β = 76.830 (1)°	Prism, red
γ = 79.801 (1)°	0.37 × 0.28 × 0.24 mm
V = 2259.92 (13) Å^3

Data collection

Bruker SMART APEXII CCD diffractometer	13589 independent reflections
Radiation source: fine-focus sealed tube	6977 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.049
φ and ω scans	θmax = 30.5°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −17→17
Tmin = 0.817, Tmax = 0.869	k = −18→18
27296 measured reflections	l = −21→21

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.148	H-atom parameters constrained
S = 0.89	w = 1/[σ^2(Fo^2) + (0.078P)^2] where P = (Fo^2 + 2Fc^2)/3
13589 reflections	(Δ/σ)max = 0.001
554 parameters	Δρmax = 0.57 e Å^−3
0 restraints	Δρmin = −0.46 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cu1	0.68239 (2)	0.52424 (2)	0.692936 (16)	0.05514 (11)
N1	0.71054 (13)	0.38671 (12)	0.64624 (10)	0.0445 (4)
N4	0.53278 (13)	0.62640 (12)	0.70936 (10)	0.0465 (4)
C6	0.78087 (15)	0.39118 (14)	0.56129 (12)	0.0427 (4)
N2	0.79346 (13)	0.56690 (12)	0.57188 (10)	0.0452 (4)
C5	0.81075 (17)	0.30693 (16)	0.51254 (14)	0.0508 (5)
C47	0.26136 (17)	0.07416 (16)	0.89020 (14)	0.0532 (5)
C10	0.82364 (15)	0.48859 (15)	0.52063 (12)	0.0432 (4)
C8	0.9198 (2)	0.4116 (2)	0.38381 (15)	0.0642 (6)
H8	0.9651	0.4182	0.3248	0.077*
C7	0.88257 (19)	0.31968 (19)	0.42279 (15)	0.0619 (6)
H7	0.9040	0.2635	0.3907	0.074*
C9	0.89094 (17)	0.49944 (17)	0.43146 (13)	0.0516 (5)
C11	0.9239 (2)	0.59746 (19)	0.39408 (15)	0.0637 (6)
H11	0.9677	0.6088	0.3347	0.076*
N3	0.67543 (14)	0.53787 (13)	0.82515 (11)	0.0518 (4)
C21	0.50958 (16)	0.65816 (14)	0.79279 (13)	0.0471 (4)
C41	0.25999 (18)	0.25710 (17)	0.78071 (14)	0.0543 (5)
C22	0.41782 (19)	0.73446 (16)	0.82027 (15)	0.0598 (6)
C1	0.66989 (17)	0.29757 (16)	0.68569 (14)	0.0524 (5)
C34	0.4223 (2)	0.11552 (18)	0.62359 (15)	0.0622 (6)
H34	0.3702	0.1658	0.5963	0.075*
B1	0.2720 (2)	0.13028 (18)	0.78139 (16)	0.0504 (5)
C20	0.58607 (18)	0.60997 (16)	0.85534 (13)	0.0510 (5)
C29	0.39552 (18)	0.08490 (16)	0.72028 (14)	0.0529 (5)
C27	0.46435 (17)	0.67113 (16)	0.64953 (14)	0.0534 (5)
C15	0.74329 (19)	0.4885 (2)	0.88297 (15)	0.0664 (6)
C35	0.16562 (17)	0.10487 (15)	0.73993 (14)	0.0518 (5)
C4	0.7636 (2)	0.21474 (17)	0.55652 (16)	0.0626 (6)
H4	0.7801	0.1567	0.5270	0.075*
C40	0.05120 (18)	0.15355 (18)	0.76247 (14)	0.0595 (5)
H40	0.0353	0.2037	0.8008	0.071*
C3	0.6946 (2)	0.21026 (17)	0.64133 (16)	0.0616 (6)
H3	0.6639	0.1494	0.6699	0.074*
C36	0.1808 (2)	0.03112 (17)	0.68181 (17)	0.0692 (6)
H36	0.2548	−0.0038	0.6639	0.083*
C30	0.47849 (19)	0.00843 (16)	0.75489 (16)	0.0593 (5)
H30	0.4669	−0.0149	0.8180	0.071*
C13	0.82750 (18)	0.65880 (16)	0.53447 (15)	0.0538 (5)
C52	0.18282 (19)	0.00629 (17)	0.93585 (14)	0.0598 (5)
H52	0.1305	−0.0082	0.9046	0.072*
C12	0.8920 (2)	0.67636 (18)	0.44447 (16)	0.0645 (6)
H12	0.9129	0.7421	0.4193	0.077*
C14	0.7909 (2)	0.74399 (18)	0.59197 (19)	0.0776 (7)
H14A	0.7130	0.7750	0.5882	0.116*
H14B	0.8417	0.7961	0.5698	0.116*
H14C	0.7945	0.7154	0.6548	0.116*
C25	0.3472 (2)	0.77843 (19)	0.75624 (18)	0.0730 (7)
H25	0.2843	0.8289	0.7711	0.088*
C19	0.5654 (2)	0.63892 (19)	0.94245 (15)	0.0662 (6)
C39	−0.0393 (2)	0.1305 (2)	0.73035 (17)	0.0706 (7)
H39	−0.1135	0.1657	0.7467	0.085*
C2	0.5973 (2)	0.2931 (2)	0.78058 (16)	0.0715 (7)
H2A	0.6466	0.2744	0.8249	0.107*
H2B	0.5461	0.2418	0.7905	0.107*
H2C	0.5527	0.3601	0.7874	0.107*
C26	0.37052 (19)	0.74751 (19)	0.67331 (17)	0.0686 (6)
H26	0.3236	0.7774	0.6311	0.082*
C42	0.3277 (2)	0.32462 (18)	0.71648 (17)	0.0687 (6)
H42	0.3839	0.2975	0.6704	0.082*
C23	0.4021 (2)	0.7644 (2)	0.90816 (18)	0.0791 (8)
H23	0.3423	0.8164	0.9256	0.095*
C28	0.4923 (2)	0.6359 (2)	0.55837 (15)	0.0689 (6)
H28A	0.5442	0.6788	0.5158	0.103*
H28B	0.4224	0.6415	0.5358	0.103*
H28C	0.5285	0.5646	0.5646	0.103*
C33	0.5203 (2)	0.0755 (2)	0.56808 (17)	0.0734 (7)
H33	0.5340	0.0998	0.5051	0.088*
C46	0.1784 (2)	0.30625 (19)	0.84660 (17)	0.0685 (6)
H46	0.1308	0.2657	0.8916	0.082*
C51	0.1798 (2)	−0.04078 (19)	1.02697 (16)	0.0725 (7)
H51	0.1254	−0.0851	1.0559	0.087*
C31	0.5780 (2)	−0.03417 (18)	0.6984 (2)	0.0752 (7)
H31	0.6307	−0.0855	0.7240	0.090*
C50	0.2571 (2)	−0.0218 (2)	1.07392 (16)	0.0809 (8)
H50	0.2563	−0.0544	1.1343	0.097*
C16	0.8404 (2)	0.4079 (3)	0.84938 (19)	0.0944 (10)
H16A	0.8307	0.3928	0.7922	0.142*
H16B	0.8399	0.3454	0.8941	0.142*
H16C	0.9128	0.4339	0.8403	0.142*
C48	0.33576 (19)	0.0921 (2)	0.94168 (15)	0.0694 (6)
H48	0.3888	0.1381	0.9142	0.083*
C32	0.5982 (3)	−0.0001 (2)	0.6044 (2)	0.0813 (8)
H32	0.6642	−0.0284	0.5665	0.098*
C45	0.1647 (3)	0.4135 (2)	0.8483 (2)	0.0831 (8)
H45	0.1085	0.4425	0.8934	0.100*
C38	−0.0206 (2)	0.0567 (2)	0.6751 (2)	0.0815 (8)
H38	−0.0816	0.0396	0.6548	0.098*
C24	0.4722 (3)	0.7188 (2)	0.96602 (17)	0.0811 (8)
H24	0.4599	0.7398	1.0232	0.097*
C37	0.0906 (3)	0.0076 (2)	0.6497 (2)	0.0875 (8)
H37	0.1052	−0.0418	0.6107	0.105*
C49	0.3354 (2)	0.0450 (2)	1.03211 (16)	0.0807 (8)
H49	0.3877	0.0587	1.0638	0.097*
C17	0.7252 (2)	0.5119 (2)	0.97209 (17)	0.0860 (8)
H17	0.7728	0.4755	1.0118	0.103*
C44	0.2327 (3)	0.4749 (2)	0.7848 (2)	0.0896 (9)
H44	0.2244	0.5461	0.7858	0.108*
C18	0.6401 (3)	0.5860 (2)	1.00090 (17)	0.0871 (8)
H18	0.6307	0.6025	1.0595	0.105*
C43	0.3139 (3)	0.4307 (2)	0.7191 (2)	0.0901 (9)
H43	0.3610	0.4725	0.6750	0.108*
C55	0.9390 (4)	0.8006 (3)	0.8818 (3)	0.1433 (16)
H55A	0.8801	0.8063	0.9372	0.172*
H55B	0.9568	0.8704	0.8555	0.172*
Cl2	1.05969 (11)	0.72871 (13)	0.91300 (11)	0.1985 (7)
Cl1	0.88168 (17)	0.75767 (16)	0.80706 (11)	0.2262 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.05564 (17)	0.06227 (18)	0.04372 (15)	0.00683 (12)	−0.00663 (11)	−0.01702 (12)
N1	0.0413 (8)	0.0514 (9)	0.0401 (8)	−0.0012 (7)	−0.0119 (7)	−0.0058 (7)
N4	0.0450 (9)	0.0483 (9)	0.0438 (9)	−0.0021 (7)	−0.0101 (7)	−0.0045 (7)
C6	0.0404 (10)	0.0484 (11)	0.0408 (10)	0.0034 (8)	−0.0165 (8)	−0.0093 (8)
N2	0.0456 (9)	0.0443 (9)	0.0444 (8)	0.0016 (7)	−0.0111 (7)	−0.0086 (7)
C5	0.0511 (11)	0.0553 (12)	0.0519 (11)	0.0035 (9)	−0.0231 (9)	−0.0172 (9)
C47	0.0479 (11)	0.0549 (12)	0.0499 (11)	0.0020 (9)	−0.0118 (9)	0.0020 (9)
C10	0.0403 (10)	0.0518 (11)	0.0370 (9)	0.0030 (8)	−0.0136 (8)	−0.0076 (8)
C8	0.0619 (14)	0.0874 (17)	0.0406 (11)	0.0024 (12)	−0.0053 (10)	−0.0209 (11)
C7	0.0668 (14)	0.0683 (15)	0.0541 (12)	0.0080 (12)	−0.0160 (11)	−0.0292 (11)
C9	0.0478 (11)	0.0642 (13)	0.0401 (10)	0.0008 (9)	−0.0103 (8)	−0.0079 (9)
C11	0.0654 (14)	0.0765 (16)	0.0409 (11)	−0.0087 (12)	−0.0055 (10)	0.0033 (11)
N3	0.0465 (9)	0.0635 (11)	0.0443 (9)	0.0042 (8)	−0.0111 (7)	−0.0147 (8)
C21	0.0461 (10)	0.0432 (10)	0.0457 (10)	−0.0018 (8)	−0.0024 (8)	−0.0039 (8)
C41	0.0525 (12)	0.0591 (12)	0.0549 (12)	−0.0059 (10)	−0.0262 (10)	−0.0010 (10)
C22	0.0585 (13)	0.0474 (11)	0.0592 (13)	0.0048 (10)	0.0041 (10)	−0.0040 (10)
C1	0.0498 (11)	0.0571 (12)	0.0511 (11)	−0.0052 (9)	−0.0205 (9)	−0.0008 (10)
C34	0.0704 (15)	0.0673 (14)	0.0530 (12)	−0.0197 (12)	−0.0149 (11)	−0.0073 (11)
B1	0.0496 (12)	0.0530 (13)	0.0467 (12)	−0.0065 (10)	−0.0163 (10)	0.0042 (10)
C20	0.0537 (11)	0.0545 (12)	0.0425 (10)	−0.0037 (9)	−0.0051 (9)	−0.0112 (9)
C29	0.0546 (12)	0.0540 (12)	0.0528 (12)	−0.0134 (9)	−0.0156 (9)	−0.0037 (9)
C27	0.0489 (11)	0.0534 (12)	0.0546 (12)	−0.0061 (9)	−0.0131 (9)	0.0018 (9)
C15	0.0611 (14)	0.0867 (17)	0.0541 (13)	0.0075 (12)	−0.0234 (11)	−0.0201 (12)
C35	0.0528 (12)	0.0480 (11)	0.0522 (11)	−0.0083 (9)	−0.0184 (9)	0.0085 (9)
C4	0.0770 (15)	0.0503 (12)	0.0712 (15)	0.0000 (11)	−0.0371 (13)	−0.0174 (11)
C40	0.0583 (13)	0.0703 (14)	0.0493 (12)	−0.0148 (11)	−0.0161 (10)	0.0033 (10)
C3	0.0721 (15)	0.0531 (13)	0.0663 (14)	−0.0143 (11)	−0.0293 (12)	−0.0025 (11)
C36	0.0656 (15)	0.0548 (13)	0.0928 (18)	−0.0038 (11)	−0.0317 (13)	−0.0105 (13)
C30	0.0603 (13)	0.0499 (12)	0.0660 (14)	−0.0066 (10)	−0.0132 (11)	−0.0053 (10)
C13	0.0533 (12)	0.0475 (11)	0.0591 (13)	−0.0003 (9)	−0.0175 (10)	−0.0042 (10)
C52	0.0569 (12)	0.0563 (13)	0.0570 (13)	0.0002 (10)	−0.0066 (10)	0.0001 (10)
C12	0.0694 (15)	0.0585 (13)	0.0605 (14)	−0.0099 (11)	−0.0167 (11)	0.0084 (11)
C14	0.0866 (18)	0.0504 (13)	0.0939 (19)	−0.0012 (12)	−0.0127 (15)	−0.0212 (13)
C25	0.0589 (14)	0.0607 (14)	0.0787 (17)	0.0161 (11)	0.0001 (12)	−0.0001 (12)
C19	0.0783 (16)	0.0717 (15)	0.0469 (12)	−0.0018 (12)	−0.0064 (11)	−0.0202 (11)
C39	0.0508 (13)	0.0873 (18)	0.0716 (15)	−0.0130 (12)	−0.0211 (12)	0.0060 (14)
C2	0.0662 (15)	0.0802 (17)	0.0606 (14)	−0.0167 (12)	−0.0046 (12)	0.0033 (12)
C26	0.0540 (13)	0.0692 (15)	0.0732 (16)	0.0040 (11)	−0.0205 (12)	0.0088 (12)
C42	0.0756 (16)	0.0580 (14)	0.0709 (15)	−0.0161 (12)	−0.0195 (13)	0.0053 (12)
C23	0.0883 (18)	0.0626 (15)	0.0663 (16)	0.0131 (13)	0.0132 (14)	−0.0171 (12)
C28	0.0735 (15)	0.0813 (16)	0.0532 (13)	−0.0056 (12)	−0.0266 (11)	−0.0022 (12)
C33	0.0940 (19)	0.0695 (16)	0.0621 (15)	−0.0298 (15)	−0.0011 (14)	−0.0236 (13)
C46	0.0734 (16)	0.0686 (15)	0.0681 (15)	−0.0073 (12)	−0.0231 (12)	−0.0140 (12)
C51	0.0747 (16)	0.0676 (15)	0.0560 (14)	−0.0004 (12)	0.0062 (12)	0.0049 (12)
C31	0.0694 (15)	0.0505 (13)	0.101 (2)	−0.0005 (11)	−0.0105 (14)	−0.0170 (13)
C50	0.0855 (18)	0.0897 (19)	0.0449 (13)	0.0210 (15)	−0.0073 (13)	0.0067 (12)
C16	0.0732 (17)	0.127 (2)	0.0800 (18)	0.0391 (16)	−0.0370 (14)	−0.0308 (17)
C48	0.0566 (13)	0.0944 (18)	0.0545 (13)	−0.0129 (12)	−0.0199 (11)	0.0073 (12)
C32	0.0869 (19)	0.0619 (16)	0.094 (2)	−0.0186 (14)	0.0112 (16)	−0.0377 (15)
C45	0.093 (2)	0.0757 (18)	0.093 (2)	0.0040 (15)	−0.0448 (17)	−0.0275 (16)
C38	0.0754 (18)	0.0813 (18)	0.099 (2)	−0.0215 (15)	−0.0462 (16)	0.0015 (16)
C24	0.102 (2)	0.0801 (18)	0.0522 (14)	0.0083 (15)	0.0013 (14)	−0.0270 (13)
C37	0.093 (2)	0.0692 (17)	0.117 (2)	−0.0079 (15)	−0.0466 (18)	−0.0268 (16)
C49	0.0669 (15)	0.114 (2)	0.0545 (14)	0.0047 (15)	−0.0214 (12)	−0.0022 (14)
C17	0.0898 (19)	0.112 (2)	0.0595 (15)	0.0126 (17)	−0.0351 (14)	−0.0222 (15)
C44	0.117 (2)	0.0577 (16)	0.110 (2)	−0.0028 (17)	−0.065 (2)	−0.0094 (17)
C18	0.107 (2)	0.110 (2)	0.0469 (13)	0.0087 (18)	−0.0257 (14)	−0.0292 (14)
C43	0.108 (2)	0.0652 (17)	0.100 (2)	−0.0293 (16)	−0.0359 (19)	0.0122 (16)
C55	0.166 (4)	0.145 (3)	0.121 (3)	0.055 (3)	−0.056 (3)	−0.061 (3)
Cl2	0.1311 (9)	0.2058 (14)	0.2069 (14)	0.0522 (9)	−0.0170 (9)	0.0023 (11)
Cl1	0.2516 (18)	0.292 (2)	0.1808 (14)	−0.0466 (16)	−0.0580 (13)	−0.1223 (14)

Geometric parameters (Å, º)

Cu1—N1	2.0188 (16)	C13—C12	1.401 (3)
Cu1—N2	2.0476 (15)	C13—C14	1.497 (3)
Cu1—N3	2.0230 (16)	C52—C51	1.392 (3)
Cu1—N4	2.0399 (15)	C52—H52	0.930
N1—C1	1.332 (3)	C12—H12	0.930
N1—C6	1.363 (2)	C14—H14A	0.960
N4—C27	1.341 (2)	C14—H14B	0.960
N4—C21	1.359 (2)	C14—H14C	0.960
C6—C5	1.401 (3)	C25—C26	1.347 (3)
C6—C10	1.441 (3)	C25—H25	0.930
N2—C13	1.327 (3)	C19—C18	1.404 (3)
N2—C10	1.360 (2)	C19—C24	1.425 (3)
C5—C4	1.414 (3)	C39—C38	1.360 (4)
C5—C7	1.428 (3)	C39—H39	0.930
C47—C48	1.385 (3)	C2—H2A	0.960
C47—C52	1.388 (3)	C2—H2B	0.960
C47—B1	1.654 (3)	C2—H2C	0.960
C10—C9	1.399 (2)	C26—H26	0.930
C8—C7	1.346 (3)	C42—C43	1.387 (4)
C8—C9	1.431 (3)	C42—H42	0.930
C8—H8	0.930	C23—C24	1.335 (4)
C7—H7	0.930	C23—H23	0.930
C9—C11	1.394 (3)	C28—H28A	0.960
C11—C12	1.358 (3)	C28—H28B	0.960
C11—H11	0.930	C28—H28C	0.960
N3—C15	1.329 (3)	C33—C32	1.363 (4)
N3—C20	1.358 (2)	C33—H33	0.930
C21—C22	1.399 (3)	C46—C45	1.400 (4)
C21—C20	1.447 (3)	C46—H46	0.930
C41—C46	1.396 (3)	C51—C50	1.369 (4)
C41—C42	1.398 (3)	C51—H51	0.930
C41—B1	1.652 (3)	C31—C32	1.384 (4)
C22—C25	1.404 (3)	C31—H31	0.930
C22—C23	1.421 (3)	C50—C49	1.364 (4)
C1—C3	1.397 (3)	C50—H50	0.930
C1—C2	1.495 (3)	C16—H16A	0.960
C34—C33	1.365 (3)	C16—H16B	0.960
C34—C29	1.416 (3)	C16—H16C	0.960
C34—H34	0.930	C48—C49	1.387 (3)
B1—C29	1.636 (3)	C48—H48	0.930
B1—C35	1.651 (3)	C32—H32	0.930
C20—C19	1.398 (3)	C45—C44	1.349 (4)
C29—C30	1.399 (3)	C45—H45	0.930
C27—C26	1.401 (3)	C38—C37	1.377 (4)
C27—C28	1.487 (3)	C38—H38	0.930
C15—C17	1.401 (3)	C24—H24	0.930
C15—C16	1.497 (3)	C37—H37	0.930
C35—C36	1.396 (3)	C49—H49	0.930
C35—C40	1.402 (3)	C17—C18	1.339 (4)
C4—C3	1.355 (3)	C17—H17	0.930
C4—H4	0.930	C44—C43	1.362 (4)
C40—C39	1.385 (3)	C44—H44	0.930
C40—H40	0.930	C18—H18	0.930
C3—H3	0.930	C43—H43	0.930
C36—C37	1.383 (3)	C55—Cl1	1.677 (4)
C36—H36	0.930	C55—Cl2	1.692 (4)
C30—C31	1.396 (3)	C55—H55A	0.970
C30—H30	0.930	C55—H55B	0.970
N1—Cu1—N2	82.54 (6)	C11—C12—C13	120.0 (2)
N1—Cu1—N3	124.07 (6)	C11—C12—H12	120.0
N1—Cu1—N4	127.96 (6)	C13—C12—H12	120.0
N2—Cu1—N3	133.27 (7)	C13—C14—H14A	109.5
N2—Cu1—N4	112.06 (6)	C13—C14—H14B	109.5
N3—Cu1—N4	82.75 (6)	H14A—C14—H14B	109.5
C1—N1—C6	118.62 (16)	C13—C14—H14C	109.5
C1—N1—Cu1	129.50 (13)	H14A—C14—H14C	109.5
C6—N1—Cu1	111.88 (12)	H14B—C14—H14C	109.5
C27—N4—C21	118.28 (17)	C26—C25—C22	120.0 (2)
C27—N4—Cu1	130.37 (14)	C26—C25—H25	120.0
C21—N4—Cu1	111.04 (12)	C22—C25—H25	120.0
N1—C6—C5	123.07 (18)	C20—C19—C18	116.4 (2)
N1—C6—C10	117.26 (16)	C20—C19—C24	119.0 (2)
C5—C6—C10	119.66 (17)	C18—C19—C24	124.6 (2)
C13—N2—C10	118.16 (17)	C38—C39—C40	120.5 (2)
C13—N2—Cu1	130.19 (13)	C38—C39—H39	119.7
C10—N2—Cu1	111.18 (12)	C40—C39—H39	119.7
C6—C5—C4	116.17 (19)	C1—C2—H2A	109.5
C6—C5—C7	119.2 (2)	C1—C2—H2B	109.5
C4—C5—C7	124.6 (2)	H2A—C2—H2B	109.5
C48—C47—C52	115.37 (19)	C1—C2—H2C	109.5
C48—C47—B1	119.98 (19)	H2A—C2—H2C	109.5
C52—C47—B1	124.64 (19)	H2B—C2—H2C	109.5
N2—C10—C9	123.30 (18)	C25—C26—C27	121.1 (2)
N2—C10—C6	116.98 (16)	C25—C26—H26	119.5
C9—C10—C6	119.71 (17)	C27—C26—H26	119.5
C7—C8—C9	121.3 (2)	C43—C42—C41	122.3 (3)
C7—C8—H8	119.4	C43—C42—H42	118.9
C9—C8—H8	119.4	C41—C42—H42	118.9
C8—C7—C5	121.1 (2)	C24—C23—C22	120.9 (2)
C8—C7—H7	119.4	C24—C23—H23	119.5
C5—C7—H7	119.4	C22—C23—H23	119.5
C11—C9—C10	116.86 (19)	C27—C28—H28A	109.5
C11—C9—C8	124.1 (2)	C27—C28—H28B	109.5
C10—C9—C8	119.0 (2)	H28A—C28—H28B	109.5
C12—C11—C9	119.9 (2)	C27—C28—H28C	109.5
C12—C11—H11	120.0	H28A—C28—H28C	109.5
C9—C11—H11	120.0	H28B—C28—H28C	109.5
C15—N3—C20	118.32 (17)	C32—C33—C34	120.3 (2)
C15—N3—Cu1	130.05 (14)	C32—C33—H33	119.8
C20—N3—Cu1	111.63 (13)	C34—C33—H33	119.8
N4—C21—C22	123.81 (19)	C41—C46—C45	123.3 (3)
N4—C21—C20	117.10 (16)	C41—C46—H46	118.3
C22—C21—C20	119.09 (18)	C45—C46—H46	118.3
C46—C41—C42	113.9 (2)	C50—C51—C52	120.0 (2)
C46—C41—B1	121.36 (19)	C50—C51—H51	120.0
C42—C41—B1	124.7 (2)	C52—C51—H51	120.0
C21—C22—C25	116.2 (2)	C32—C31—C30	120.0 (2)
C21—C22—C23	119.7 (2)	C32—C31—H31	120.0
C25—C22—C23	124.0 (2)	C30—C31—H31	120.0
N1—C1—C3	121.86 (19)	C49—C50—C51	120.0 (2)
N1—C1—C2	117.64 (19)	C49—C50—H50	120.0
C3—C1—C2	120.5 (2)	C51—C50—H50	120.0
C33—C34—C29	123.8 (2)	C15—C16—H16A	109.5
C33—C34—H34	118.1	C15—C16—H16B	109.5
C29—C34—H34	118.1	H16A—C16—H16B	109.5
C29—B1—C35	108.75 (17)	C15—C16—H16C	109.5
C29—B1—C41	112.24 (17)	H16A—C16—H16C	109.5
C35—B1—C41	109.69 (16)	H16B—C16—H16C	109.5
C29—B1—C47	109.92 (16)	C47—C48—C49	123.5 (2)
C35—B1—C47	109.73 (16)	C47—C48—H48	118.2
C41—B1—C47	106.49 (17)	C49—C48—H48	118.2
N3—C20—C19	123.4 (2)	C33—C32—C31	119.2 (2)
N3—C20—C21	117.14 (17)	C33—C32—H32	120.4
C19—C20—C21	119.45 (19)	C31—C32—H32	120.4
C30—C29—C34	114.0 (2)	C44—C45—C46	120.2 (3)
C30—C29—B1	124.85 (18)	C44—C45—H45	119.9
C34—C29—B1	120.96 (19)	C46—C45—H45	119.9
N4—C27—C26	120.6 (2)	C39—C38—C37	118.6 (2)
N4—C27—C28	117.24 (18)	C39—C38—H38	120.7
C26—C27—C28	122.2 (2)	C37—C38—H38	120.7
N3—C15—C17	121.0 (2)	C23—C24—C19	121.7 (2)
N3—C15—C16	117.83 (19)	C23—C24—H24	119.1
C17—C15—C16	121.2 (2)	C19—C24—H24	119.1
C36—C35—C40	114.17 (19)	C38—C37—C36	120.6 (3)
C36—C35—B1	123.11 (19)	C38—C37—H37	119.7
C40—C35—B1	122.69 (19)	C36—C37—H37	119.7
C3—C4—C5	120.6 (2)	C50—C49—C48	119.0 (3)
C3—C4—H4	119.7	C50—C49—H49	120.5
C5—C4—H4	119.7	C48—C49—H49	120.5
C39—C40—C35	123.2 (2)	C18—C17—C15	120.9 (2)
C39—C40—H40	118.4	C18—C17—H17	119.5
C35—C40—H40	118.4	C15—C17—H17	119.5
C4—C3—C1	119.7 (2)	C45—C44—C43	118.7 (3)
C4—C3—H3	120.2	C45—C44—H44	120.6
C1—C3—H3	120.2	C43—C44—H44	120.6
C37—C36—C35	122.9 (2)	C17—C18—C19	119.9 (2)
C37—C36—H36	118.6	C17—C18—H18	120.1
C35—C36—H36	118.6	C19—C18—H18	120.1
C31—C30—C29	122.6 (2)	C44—C43—C42	121.5 (3)
C31—C30—H30	118.7	C44—C43—H43	119.3
C29—C30—H30	118.7	C42—C43—H43	119.3
N2—C13—C12	121.7 (2)	Cl1—C55—Cl2	117.4 (2)
N2—C13—C14	116.87 (19)	Cl1—C55—H55A	107.9
C12—C13—C14	121.4 (2)	Cl2—C55—H55A	107.9
C47—C52—C51	122.1 (2)	Cl1—C55—H55B	107.9
C47—C52—H52	119.0	Cl2—C55—H55B	107.9
C51—C52—H52	118.9	H55A—C55—H55B	107.2