Bis{N-[(Z)-(3-Methyl-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-4-yl­idene)(phen­yl)meth­yl]benzyl­amido-κ²N,O}copper(II)

The Cu atom in the title compound, [Cu(C₂₄H₂₀N₃O)₂], is chelated by two deprotonated 4-[(benzyl­amino)phenyl­methyl­ene]-5-methyl-2-phenyl­pyrazol-3-one ligands through their amide N and carbonyl O atoms in a distorted square-planar geometry.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.036
• wR factor = 0.111
• Data-to-parameter ratio = 17.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.62 Ratio

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

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

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Bis{[(Z)-(3-Methyl-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-4- ylidene)(phenyl)methyl]benzylamido-κ²N,O}copper(II)

Crystal data

[Cu(C24H20N3O)2]	F(000) = 1660
Mr = 796.40	Dx = 1.296 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 975 reflections
a = 14.718 (2) Å	θ = 2.6–26.6°
b = 18.686 (2) Å	µ = 0.58 mm^−1
c = 15.320 (2) Å	T = 295 K
β = 104.337 (2)°	Irregular block, black
V = 4082.2 (9) Å^3	0.49 × 0.48 × 0.27 mm
Z = 4

Data collection

Bruker SMART area-detector diffractometer	8912 independent reflections
Radiation source: fine-focus sealed tube	6429 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
ω and φ scans	θmax = 27.1°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→18
Tmin = 0.730, Tmax = 0.859	k = −23→14
24434 measured reflections	l = −19→19

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.111	H-atom parameters constrained
S = 0.99	w = 1/[σ^2(Fo^2) + (0.055P)^2 + 1.4386P] where P = (Fo^2 + 2Fc^2)/3
8912 reflections	(Δ/σ)max = 0.001
516 parameters	Δρmax = 0.23 e Å^−3
0 restraints	Δρmin = −0.31 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cu1	0.33873 (2)	0.32702 (1)	0.52305 (2)	0.04371 (9)
O1	0.4713 (1)	0.3237 (1)	0.5744 (1)	0.0491 (3)
O2	0.2312 (1)	0.3393 (1)	0.4234 (1)	0.0490 (3)
N1	0.6129 (1)	0.3845 (1)	0.6200 (1)	0.0413 (4)
N2	0.6456 (1)	0.4534 (1)	0.6444 (1)	0.0471 (4)
N3	0.3234 (1)	0.4237 (1)	0.5690 (1)	0.0470 (4)
N4	0.0722 (1)	0.3125 (1)	0.3751 (1)	0.0525 (4)
N5	0.0119 (1)	0.2566 (1)	0.3828 (2)	0.0647 (5)
N6	0.3260 (1)	0.2213 (1)	0.5195 (1)	0.0449 (4)
C1	0.6785 (1)	0.3283 (1)	0.6244 (1)	0.041 (1)
C2	0.6578 (1)	0.2701 (1)	0.5678 (1)	0.047 (1)
C3	0.7246 (2)	0.2171 (1)	0.5717 (2)	0.056 (1)
C4	0.8108 (2)	0.2220 (1)	0.6318 (2)	0.064 (1)
C5	0.8309 (2)	0.2797 (2)	0.6891 (2)	0.066 (1)
C6	0.7653 (1)	0.3330 (1)	0.6856 (2)	0.054 (1)
C7	0.5174 (1)	0.3821 (1)	0.5981 (1)	0.040 (1)
C8	0.4863 (1)	0.4513 (1)	0.6105 (1)	0.040 (1)
C9	0.5701 (1)	0.4926 (1)	0.6383 (1)	0.045 (1)
C10	0.5828 (2)	0.5712 (1)	0.6559 (2)	0.065 (1)
C11	0.3903 (1)	0.4687 (1)	0.6043 (1)	0.042 (1)
C12	0.3695 (1)	0.5382 (1)	0.6437 (1)	0.045 (1)
C13	0.3280 (2)	0.5940 (1)	0.5895 (2)	0.067 (1)
C14	0.3094 (2)	0.6574 (1)	0.6283 (2)	0.087 (1)
C15	0.3319 (2)	0.6651 (1)	0.7200 (2)	0.079 (1)
C16	0.3708 (2)	0.6097 (2)	0.7736 (2)	0.074 (1)
C17	0.3903 (2)	0.5460 (1)	0.7358 (2)	0.060 (1)
C18	0.2255 (1)	0.4404 (1)	0.5693 (2)	0.058 (1)
C19	0.1811 (2)	0.3797 (1)	0.6090 (2)	0.055 (1)
C20	0.2313 (2)	0.3375 (2)	0.6776 (2)	0.072 (1)
C21	0.1873 (3)	0.2823 (2)	0.7122 (2)	0.099 (1)
C22	0.0934 (3)	0.2701 (2)	0.6782 (3)	0.103 (1)
C23	0.0429 (2)	0.3124 (2)	0.6111 (2)	0.088 (1)
C24	0.0858 (2)	0.3668 (2)	0.5767 (2)	0.066 (1)
C25	0.0337 (2)	0.3781 (1)	0.3360 (2)	0.055 (1)
C26	0.0886 (2)	0.4310 (2)	0.3133 (2)	0.079 (1)
C27	0.0484 (2)	0.4952 (2)	0.2787 (2)	0.093 (1)
C28	−0.0458 (2)	0.5066 (2)	0.2647 (2)	0.084 (1)
C29	−0.1005 (2)	0.4532 (2)	0.2854 (2)	0.080 (1)
C30	−0.0622 (2)	0.3892 (2)	0.3217 (2)	0.068 (1)
C31	0.1623 (1)	0.2961 (1)	0.4183 (1)	0.046 (1)
C32	0.1615 (1)	0.2267 (1)	0.4528 (2)	0.048 (1)
C33	0.0650 (2)	0.2060 (1)	0.4281 (2)	0.062 (1)
C34	0.0177 (2)	0.1393 (2)	0.4488 (3)	0.097 (1)
C35	0.2444 (1)	0.1886 (1)	0.4959 (1)	0.046 (1)
C36	0.2353 (2)	0.1105 (1)	0.5127 (2)	0.055 (1)
C37	0.2301 (2)	0.0872 (2)	0.5968 (2)	0.078 (1)
C38	0.2180 (2)	0.0155 (2)	0.6121 (3)	0.101 (1)
C39	0.2108 (2)	−0.0329 (2)	0.5438 (3)	0.099 (1)
C40	0.2178 (2)	−0.0107 (2)	0.4607 (3)	0.091 (1)
C41	0.2301 (2)	0.0610 (1)	0.4446 (2)	0.072 (1)
C42	0.4110 (1)	0.1768 (1)	0.5464 (2)	0.047 (1)
C43	0.4529 (1)	0.1600 (1)	0.4689 (2)	0.051 (1)
C44	0.4451 (2)	0.2043 (2)	0.3963 (2)	0.069 (1)
C45	0.4918 (2)	0.1883 (2)	0.3299 (2)	0.094 (1)
C46	0.5452 (2)	0.1269 (3)	0.3368 (3)	0.104 (1)
C47	0.5505 (2)	0.0821 (2)	0.4065 (3)	0.101 (1)
C48	0.5054 (2)	0.0979 (2)	0.4724 (2)	0.075 (1)
H2	0.5994	0.2664	0.5272	0.057*
H3	0.7109	0.1779	0.5333	0.067*
H4	0.8554	0.1864	0.6337	0.077*
H5	0.8889	0.2828	0.7304	0.079*
H6	0.7792	0.3720	0.7243	0.065*
H10a	0.6456	0.5847	0.6555	0.097*
H10b	0.5717	0.5822	0.7136	0.097*
H10c	0.5392	0.5972	0.6098	0.097*
H13	0.3125	0.5890	0.5272	0.081*
H14	0.2814	0.6951	0.5918	0.104*
H15	0.3206	0.7083	0.7456	0.094*
H16	0.3844	0.6145	0.8360	0.088*
H17	0.4175	0.5084	0.7728	0.072*
H18a	0.1896	0.4492	0.5081	0.069*
H18b	0.2241	0.4835	0.6042	0.069*
H20	0.2950	0.3458	0.7009	0.087*
H21	0.2216	0.2537	0.7584	0.119*
H22	0.0642	0.2329	0.7010	0.124*
H23	−0.0210	0.3043	0.5886	0.106*
H24	0.0506	0.3955	0.5311	0.079*
H26	0.1526	0.4236	0.3212	0.095*
H27	0.0862	0.5311	0.2647	0.112*
H28	−0.0722	0.5499	0.2416	0.101*
H29	−0.1648	0.4601	0.2747	0.096*
H30	−0.1003	0.3538	0.3365	0.082*
H34a	−0.0491	0.1450	0.4290	0.145*
H34b	0.0350	0.1307	0.5125	0.145*
H34c	0.0368	0.0995	0.4180	0.145*
H37	0.2346	0.1199	0.6434	0.094*
H38	0.2148	0.0000	0.6690	0.121*
H39	0.2012	−0.0810	0.5539	0.118*
H40	0.2141	−0.0440	0.4148	0.109*
H41	0.2350	0.0759	0.3880	0.087*
H42a	0.3955	0.1324	0.5722	0.057*
H42b	0.4572	0.2017	0.5926	0.057*
H44	0.4084	0.2454	0.3912	0.082*
H45	0.4870	0.2189	0.2811	0.113*
H46	0.5776	0.1166	0.2933	0.125*
H47	0.5849	0.0400	0.4100	0.121*
H48	0.5102	0.0665	0.5204	0.089*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0300 (1)	0.0432 (2)	0.0559 (2)	−0.0025 (1)	0.0067 (1)	−0.0070 (1)
O1	0.032 (1)	0.041 (1)	0.070 (1)	−0.003 (1)	0.005 (1)	−0.009 (1)
O2	0.033 (1)	0.053 (1)	0.058 (1)	−0.004 (1)	0.004 (1)	0.002 (1)
N1	0.033 (1)	0.042 (1)	0.048 (1)	−0.005 (1)	0.009 (1)	−0.003 (1)
N2	0.039 (1)	0.046 (1)	0.056 (1)	−0.010 (1)	0.012 (1)	−0.004 (1)
N3	0.034 (1)	0.047 (1)	0.060 (1)	0.000 (1)	0.013 (1)	−0.008 (1)
N4	0.033 (1)	0.067 (1)	0.054 (1)	−0.004 (1)	0.004 (1)	−0.007 (1)
N5	0.037 (1)	0.077 (1)	0.077 (1)	−0.014 (1)	0.007 (1)	−0.011 (1)
N6	0.036 (1)	0.045 (1)	0.053 (1)	−0.003 (1)	0.009 (1)	−0.003 (1)
C1	0.032 (1)	0.047 (1)	0.045 (1)	−0.002 (1)	0.011 (1)	0.007 (1)
C2	0.037 (1)	0.051 (1)	0.053 (1)	0.000 (1)	0.008 (1)	0.002 (1)
C3	0.054 (1)	0.051 (1)	0.066 (2)	0.004 (1)	0.020 (1)	0.003 (1)
C4	0.045 (1)	0.062 (2)	0.086 (2)	0.012 (1)	0.020 (1)	0.017 (1)
C5	0.033 (1)	0.079 (2)	0.080 (2)	0.002 (1)	0.002 (1)	0.011 (1)
C6	0.037 (1)	0.063 (1)	0.059 (1)	−0.006 (1)	0.005 (1)	0.000 (1)
C7	0.032 (1)	0.045 (1)	0.041 (1)	−0.003 (1)	0.007 (1)	−0.001 (1)
C8	0.038 (1)	0.042 (1)	0.040 (1)	−0.004 (1)	0.010 (1)	−0.001 (1)
C9	0.044 (1)	0.046 (1)	0.047 (1)	−0.008 (1)	0.014 (1)	−0.004 (1)
C10	0.055 (1)	0.049 (1)	0.092 (2)	−0.013 (1)	0.021 (1)	−0.009 (1)
C11	0.042 (1)	0.044 (1)	0.040 (1)	0.000 (1)	0.012 (1)	0.000 (1)
C12	0.042 (1)	0.044 (1)	0.051 (1)	−0.002 (1)	0.017 (1)	−0.004 (1)
C13	0.098 (2)	0.054 (1)	0.059 (2)	0.013 (1)	0.037 (1)	0.011 (1)
C14	0.127 (3)	0.052 (2)	0.100 (2)	0.026 (2)	0.063 (2)	0.020 (2)
C15	0.097 (2)	0.054 (2)	0.101 (2)	−0.002 (1)	0.054 (2)	−0.020 (2)
C16	0.070 (2)	0.086 (2)	0.065 (2)	0.005 (1)	0.016 (1)	−0.028 (2)
C17	0.054 (1)	0.070 (2)	0.053 (1)	0.013 (1)	0.008 (1)	−0.007 (1)
C18	0.037 (1)	0.057 (1)	0.080 (2)	0.003 (2)	0.015 (1)	−0.012 (1)
C19	0.042 (1)	0.072 (2)	0.054 (1)	−0.002 (1)	0.018 (1)	−0.015 (1)
C20	0.057 (1)	0.101 (2)	0.061 (2)	−0.002 (1)	0.020 (1)	−0.003 (1)
C21	0.096 (2)	0.136 (3)	0.073 (2)	0.003 (2)	0.037 (2)	0.028 (2)
C22	0.096 (3)	0.135 (3)	0.093 (2)	−0.030 (2)	0.052 (2)	0.012 (2)
C23	0.063 (2)	0.134 (3)	0.077 (2)	−0.026 (2)	0.034 (2)	−0.009 (2)
C24	0.044 (1)	0.096 (2)	0.062 (2)	−0.008 (1)	0.021 (1)	−0.012 (1)
C25	0.041 (1)	0.073 (2)	0.048 (1)	0.004 (1)	0.003 (1)	−0.010 (1)
C26	0.048 (1)	0.097 (2)	0.090 (2)	0.012 (1)	0.015 (1)	0.028 (2)
C27	0.071 (2)	0.099 (2)	0.105 (2)	0.014 (2)	0.015 (2)	0.034 (2)
C28	0.073 (2)	0.092 (2)	0.081 (2)	0.028 (2)	0.007 (2)	0.004 (2)
C29	0.051 (1)	0.102 (2)	0.080 (2)	0.024 (2)	0.005 (1)	−0.017 (2)
C30	0.042 (1)	0.083 (2)	0.077 (2)	0.006 (1)	0.010 (1)	−0.016 (1)
C31	0.033 (1)	0.057 (1)	0.046 (1)	−0.002 (1)	0.008 (1)	−0.010 (1)
C32	0.036 (1)	0.052 (1)	0.056 (1)	−0.009 (1)	0.010 (1)	−0.009 (1)
C33	0.041 (1)	0.066 (2)	0.077 (2)	−0.014 (1)	0.011 (1)	−0.010 (1)
C34	0.049 (2)	0.085 (2)	0.153 (3)	−0.025 (2)	0.018 (2)	0.004 (2)
C35	0.043 (1)	0.046 (1)	0.050 (1)	−0.008 (1)	0.013 (1)	−0.007 (1)
C36	0.042 (1)	0.051 (1)	0.070 (2)	−0.008 (1)	0.011 (1)	−0.003 (1)
C37	0.094 (2)	0.064 (2)	0.090 (2)	−0.008 (1)	0.047 (2)	0.003 (1)
C38	0.110 (3)	0.076 (2)	0.139 (3)	−0.002 (2)	0.071 (2)	0.027 (2)
C39	0.081 (2)	0.056 (2)	0.161 (4)	−0.011 (2)	0.035 (2)	0.013 (2)
C40	0.090 (2)	0.051 (2)	0.117 (3)	−0.008 (1)	−0.003 (2)	−0.015 (2)
C41	0.075 (2)	0.056 (2)	0.075 (2)	−0.008 (1)	0.000 (1)	−0.010 (1)
C42	0.039 (1)	0.044 (1)	0.056 (1)	−0.002 (1)	0.006 (1)	0.000 (1)
C43	0.037 (1)	0.055 (1)	0.057 (1)	−0.007 (1)	0.004 (1)	−0.016 (1)
C44	0.063 (2)	0.083 (2)	0.060 (2)	−0.005 (1)	0.015 (1)	−0.013 (1)
C45	0.084 (2)	0.139 (3)	0.060 (2)	−0.026 (2)	0.019 (2)	−0.017 (2)
C46	0.064 (2)	0.168 (4)	0.084 (2)	−0.013 (2)	0.025 (2)	−0.063 (3)
C47	0.072 (2)	0.126 (3)	0.101 (3)	0.017 (2)	0.018 (2)	−0.059 (2)
C48	0.064 (2)	0.074 (2)	0.079 (2)	0.012 (1)	0.005 (1)	−0.025 (1)

Geometric parameters (Å, º)

Cu1—O1	1.916 (1)	C36—C37	1.380 (4)
Cu1—O2	1.922 (1)	C36—C41	1.383 (3)
Cu1—N3	1.973 (2)	C37—C38	1.378 (4)
Cu1—N6	1.984 (2)	C38—C39	1.367 (5)
O1—C7	1.287 (2)	C39—C40	1.366 (5)
O2—C31	1.283 (2)	C40—C41	1.384 (4)
N1—C7	1.363 (2)	C42—C43	1.500 (3)
N1—N2	1.392 (2)	C43—C44	1.368 (4)
N1—C1	1.417 (2)	C43—C48	1.389 (3)
N2—C9	1.316 (3)	C44—C45	1.394 (4)
N3—C11	1.304 (2)	C45—C46	1.379 (5)
N3—C18	1.476 (2)	C46—C47	1.345 (5)
N4—C31	1.363 (3)	C47—C48	1.371 (4)
N4—N5	1.395 (3)	C2—H2	0.93
N4—C25	1.420 (3)	C3—H3	0.93
N5—C33	1.310 (3)	C4—H4	0.93
N6—C35	1.316 (2)	C5—H5	0.93
N6—C42	1.474 (2)	C6—H6	0.93
C1—C2	1.379 (3)	C10—H10a	0.96
C1—C6	1.387 (3)	C10—H10b	0.96
C2—C3	1.386 (3)	C10—H10c	0.96
C3—C4	1.373 (3)	C13—H13	0.93
C4—C5	1.376 (4)	C14—H14	0.93
C5—C6	1.378 (3)	C15—H15	0.93
C7—C8	1.401 (3)	C16—H16	0.93
C8—C9	1.428 (3)	C17—H17	0.93
C8—C11	1.430 (3)	C18—H18a	0.97
C9—C10	1.496 (3)	C18—H18b	0.97
C11—C12	1.496 (3)	C20—H20	0.93
C12—C17	1.375 (3)	C21—H21	0.93
C12—C13	1.377 (3)	C22—H22	0.93
C13—C14	1.384 (4)	C23—H23	0.93
C14—C15	1.369 (4)	C24—H24	0.93
C15—C16	1.357 (4)	C26—H26	0.93
C16—C17	1.384 (3)	C27—H27	0.93
C18—C19	1.509 (3)	C28—H28	0.93
C19—C20	1.374 (4)	C29—H29	0.93
C19—C24	1.388 (3)	C30—H30	0.93
C20—C21	1.390 (4)	C34—H34a	0.96
C21—C22	1.370 (5)	C34—H34b	0.96
C22—C23	1.362 (5)	C34—H34c	0.96
C23—C24	1.369 (4)	C37—H37	0.93
C25—C26	1.375 (4)	C38—H38	0.93
C25—C30	1.389 (3)	C39—H39	0.93
C26—C27	1.384 (4)	C40—H40	0.93
C27—C28	1.366 (4)	C41—H41	0.93
C28—C29	1.368 (4)	C42—H42a	0.97
C29—C30	1.378 (4)	C42—H42b	0.97
C31—C32	1.400 (3)	C44—H44	0.93
C32—C35	1.427 (3)	C45—H45	0.93
C32—C33	1.430 (3)	C46—H46	0.93
C33—C34	1.499 (4)	C47—H47	0.93
C35—C36	1.493 (3)	C48—H48	0.93
O1—Cu1—O2	152.25 (7)	C44—C43—C42	123.3 (2)
O1—Cu1—N3	94.45 (6)	C48—C43—C42	118.6 (2)
O1—Cu1—N6	93.39 (6)	C43—C44—C45	120.4 (3)
O2—Cu1—N3	91.70 (7)	C46—C45—C44	119.8 (3)
O2—Cu1—N6	92.50 (6)	C47—C46—C45	119.9 (3)
N3—Cu1—N6	154.63 (7)	C46—C47—C48	120.5 (3)
C7—O1—Cu1	120.0 (1)	C47—C48—C43	121.2 (3)
C31—O2—Cu1	117.1 (1)	C1—C2—H2	120.3
C7—N1—N2	111.4 (2)	C3—C2—H2	120.3
C7—N1—C1	129.5 (2)	C4—C3—H3	119.7
N2—N1—C1	119.1 (2)	C2—C3—H3	119.7
C9—N2—N1	105.5 (2)	C3—C4—H4	120.1
C11—N3—C18	120.0 (2)	C5—C4—H4	120.1
C11—N3—Cu1	126.7 (1)	C6—C5—H5	119.9
C18—N3—Cu1	113.1 (1)	C4—C5—H5	119.9
C31—N4—N5	110.8 (2)	C5—C6—H6	120.0
C31—N4—C25	129.7 (2)	C1—C6—H6	120.0
N5—N4—C25	119.1 (2)	C9—C10—H10a	109.5
C33—N5—N4	106.0 (2)	C9—C10—H10b	109.5
C35—N6—C42	118.0 (2)	H10a—C10—H10b	109.5
C35—N6—Cu1	123.0 (1)	C9—C10—H10c	109.5
C42—N6—Cu1	119.1 (1)	H10a—C10—H10c	109.5
C2—C1—C6	119.9 (2)	H10b—C10—H10c	109.5
C2—C1—N1	120.8 (2)	C12—C13—H13	120.2
C6—C1—N1	119.3 (2)	C14—C13—H13	120.2
C1—C2—C3	119.5 (2)	C15—C14—H14	119.7
C4—C3—C2	120.6 (2)	C13—C14—H14	119.7
C3—C4—C5	119.8 (2)	C16—C15—H15	120.0
C6—C5—C4	120.2 (2)	C14—C15—H15	120.0
C5—C6—C1	120.0 (2)	C15—C16—H16	119.9
O1—C7—N1	122.5 (2)	C17—C16—H16	119.9
O1—C7—C8	130.8 (2)	C12—C17—H17	119.8
N1—C7—C8	106.7 (2)	C16—C17—H17	119.8
C7—C8—C9	104.7 (2)	N3—C18—H18a	109.4
C7—C8—C11	123.4 (2)	C19—C18—H18a	109.4
C9—C8—C11	131.6 (2)	N3—C18—H18b	109.4
N2—C9—C8	111.8 (2)	C19—C18—H18b	109.4
N2—C9—C10	118.0 (2)	H18a—C18—H18b	108.0
C8—C9—C10	130.1 (2)	C19—C20—H20	119.8
N3—C11—C8	120.8 (2)	C21—C20—H20	119.8
N3—C11—C12	121.2 (2)	C22—C21—H21	120.0
C8—C11—C12	117.9 (2)	C20—C21—H21	120.0
C17—C12—C13	119.4 (2)	C23—C22—H22	120.0
C17—C12—C11	119.4 (2)	C21—C22—H22	120.0
C13—C12—C11	121.2 (2)	C22—C23—H23	119.9
C12—C13—C14	119.7 (2)	C24—C23—H23	119.9
C15—C14—C13	120.5 (3)	C23—C24—H24	119.5
C16—C15—C14	120.0 (2)	C19—C24—H24	119.5
C15—C16—C17	120.2 (3)	C25—C26—H26	120.1
C12—C17—C16	120.3 (2)	C27—C26—H26	120.1
N3—C18—C19	111.4 (2)	C28—C27—H27	119.5
C20—C19—C24	118.5 (2)	C26—C27—H27	119.5
C20—C19—C18	122.3 (2)	C27—C28—H28	120.6
C24—C19—C18	119.2 (2)	C29—C28—H28	120.6
C19—C20—C21	120.3 (3)	C28—C29—H29	119.3
C22—C21—C20	120.0 (3)	C30—C29—H29	119.3
C23—C22—C21	120.1 (3)	C29—C30—H30	120.3
C22—C23—C24	120.2 (3)	C25—C30—H30	120.3
C23—C24—C19	120.9 (3)	C33—C34—H34a	109.5
C26—C25—C30	119.4 (2)	C33—C34—H34b	109.5
C26—C25—N4	121.9 (2)	H34a—C34—H34b	109.5
C30—C25—N4	118.7 (2)	C33—C34—H34c	109.5
C25—C26—C27	119.8 (3)	H34a—C34—H34c	109.5
C28—C27—C26	121.1 (3)	H34b—C34—H34c	109.5
C27—C28—C29	118.8 (3)	C38—C37—H37	119.8
C28—C29—C30	121.4 (3)	C36—C37—H37	119.8
C29—C30—C25	119.4 (3)	C39—C38—H38	120.0
O2—C31—N4	123.2 (2)	C37—C38—H38	120.0
O2—C31—C32	129.8 (2)	C40—C39—H39	119.9
N4—C31—C32	107.0 (2)	C38—C39—H39	119.9
C31—C32—C35	123.4 (2)	C39—C40—H40	119.9
C31—C32—C33	104.6 (2)	C41—C40—H40	119.9
C35—C32—C33	131.8 (2)	C40—C41—H41	120.1
N5—C33—C32	111.6 (2)	C36—C41—H41	120.1
N5—C33—C34	117.7 (2)	N6—C42—H42a	109.1
C32—C33—C34	130.7 (2)	C43—C42—H42a	109.1
N6—C35—C32	120.8 (2)	N6—C42—H42b	109.1
N6—C35—C36	121.4 (2)	C43—C42—H42b	109.1
C32—C35—C36	117.8 (2)	H42a—C42—H42b	107.8
C37—C36—C41	119.2 (2)	C43—C44—H44	119.8
C37—C36—C35	119.8 (2)	C45—C44—H44	119.8
C41—C36—C35	120.9 (2)	C46—C45—H45	120.1
C38—C37—C36	120.3 (3)	C44—C45—H45	120.1
C39—C38—C37	120.1 (3)	C47—C46—H46	120.0
C40—C39—C38	120.3 (3)	C45—C46—H46	120.0
C39—C40—C41	120.2 (3)	C46—C47—H47	119.8
C40—C41—C36	119.9 (3)	C48—C47—H47	119.8
N6—C42—C43	112.6 (2)	C47—C48—H48	119.4
C44—C43—C48	118.1 (2)	C43—C48—H48	119.4
O2—Cu1—O1—C7	83.3 (2)	Cu1—N3—C18—C19	46.7 (2)
N3—Cu1—O1—C7	−19.0 (2)	N3—C18—C19—C20	33.8 (3)
N6—Cu1—O1—C7	−174.8 (2)	N3—C18—C19—C24	−147.6 (2)
O1—Cu1—O2—C31	138.4 (2)	C24—C19—C20—C21	1.2 (4)
N3—Cu1—O2—C31	−118.7 (2)	C18—C19—C20—C21	179.8 (3)
N6—Cu1—O2—C31	36.3 (2)	C19—C20—C21—C22	−0.3 (5)
C7—N1—N2—C9	0.7 (2)	C20—C21—C22—C23	−0.6 (5)
C1—N1—N2—C9	−176.7 (2)	C21—C22—C23—C24	0.7 (5)
O1—Cu1—N3—C11	12.0 (2)	C22—C23—C24—C19	0.3 (5)
O2—Cu1—N3—C11	−141.0 (2)	C20—C19—C24—C23	−1.2 (4)
N6—Cu1—N3—C11	119.6 (2)	C18—C19—C24—C23	−179.9 (2)
O1—Cu1—N3—C18	−161.8 (2)	C31—N4—C25—C26	19.6 (4)
O2—Cu1—N3—C18	45.3 (2)	N5—N4—C25—C26	−169.5 (2)
N6—Cu1—N3—C18	−54.2 (2)	C31—N4—C25—C30	−159.5 (2)
C31—N4—N5—C33	−1.6 (3)	N5—N4—C25—C30	11.5 (3)
C25—N4—N5—C33	−174.2 (2)	C30—C25—C26—C27	1.6 (4)
O1—Cu1—N6—C35	174.1 (2)	N4—C25—C26—C27	−177.5 (3)
O2—Cu1—N6—C35	−33.0 (2)	C25—C26—C27—C28	−1.4 (5)
N3—Cu1—N6—C35	66.3 (2)	C26—C27—C28—C29	−0.2 (5)
O1—Cu1—N6—C42	−4.5 (2)	C27—C28—C29—C30	1.6 (5)
O2—Cu1—N6—C42	148.4 (2)	C28—C29—C30—C25	−1.3 (4)
N3—Cu1—N6—C42	−112.3 (2)	C26—C25—C30—C29	−0.3 (4)
C7—N1—C1—C2	32.0 (3)	N4—C25—C30—C29	178.8 (2)
N2—N1—C1—C2	−151.2 (2)	Cu1—O2—C31—N4	155.0 (2)
C7—N1—C1—C6	−149.2 (2)	Cu1—O2—C31—C32	−25.0 (3)
N2—N1—C1—C6	27.6 (3)	N5—N4—C31—O2	−178.1 (2)
C6—C1—C2—C3	−0.9 (3)	C25—N4—C31—O2	−6.5 (3)
N1—C1—C2—C3	177.9 (2)	N5—N4—C31—C32	1.9 (2)
C1—C2—C3—C4	0.4 (3)	C25—N4—C31—C32	173.5 (2)
C2—C3—C4—C5	0.5 (4)	O2—C31—C32—C35	−5.5 (4)
C3—C4—C5—C6	−0.8 (4)	N4—C31—C32—C35	174.5 (2)
C4—C5—C6—C1	0.3 (4)	O2—C31—C32—C33	178.6 (2)
C2—C1—C6—C5	0.6 (3)	N4—C31—C32—C33	−1.4 (2)
N1—C1—C6—C5	−178.2 (2)	N4—N5—C33—C32	0.7 (3)
Cu1—O1—C7—N1	−168.2 (1)	N4—N5—C33—C34	178.4 (2)
Cu1—O1—C7—C8	14.6 (3)	C31—C32—C33—N5	0.5 (3)
N2—N1—C7—O1	−179.2 (2)	C35—C32—C33—N5	−175.0 (2)
C1—N1—C7—O1	−2.2 (3)	C31—C32—C33—C34	−176.9 (3)
N2—N1—C7—C8	−1.4 (2)	C35—C32—C33—C34	7.7 (5)
C1—N1—C7—C8	175.6 (2)	C42—N6—C35—C32	−167.7 (2)
O1—C7—C8—C9	179.0 (2)	Cu1—N6—C35—C32	13.7 (3)
N1—C7—C8—C9	1.4 (2)	C42—N6—C35—C36	12.0 (3)
O1—C7—C8—C11	4.9 (3)	Cu1—N6—C35—C36	−166.6 (2)
N1—C7—C8—C11	−172.6 (2)	C31—C32—C35—N6	11.8 (3)
N1—N2—C9—C8	0.3 (2)	C33—C32—C35—N6	−173.5 (2)
N1—N2—C9—C10	−176.7 (2)	C31—C32—C35—C36	−167.9 (2)
C7—C8—C9—N2	−1.1 (2)	C33—C32—C35—C36	6.8 (4)
C11—C8—C9—N2	172.3 (2)	N6—C35—C36—C37	81.4 (3)
C7—C8—C9—C10	175.4 (2)	C32—C35—C36—C37	−99.0 (3)
C11—C8—C9—C10	−11.2 (4)	N6—C35—C36—C41	−100.0 (3)
C18—N3—C11—C8	175.5 (2)	C32—C35—C36—C41	79.7 (3)
Cu1—N3—C11—C8	2.1 (3)	C41—C36—C37—C38	−1.2 (4)
C18—N3—C11—C12	−1.4 (3)	C35—C36—C37—C38	177.5 (3)
Cu1—N3—C11—C12	−174.8 (1)	C36—C37—C38—C39	−0.3 (5)
C7—C8—C11—N3	−13.9 (3)	C37—C38—C39—C40	1.6 (5)
C9—C8—C11—N3	173.8 (2)	C38—C39—C40—C41	−1.4 (5)
C7—C8—C11—C12	163.0 (2)	C39—C40—C41—C36	−0.1 (5)
C9—C8—C11—C12	−9.3 (3)	C37—C36—C41—C40	1.4 (4)
N3—C11—C12—C17	105.0 (2)	C35—C36—C41—C40	−177.3 (2)
C8—C11—C12—C17	−71.9 (3)	C35—N6—C42—C43	92.1 (2)
N3—C11—C12—C13	−73.5 (3)	Cu1—N6—C42—C43	−89.2 (2)
C8—C11—C12—C13	109.6 (2)	N6—C42—C43—C44	29.3 (3)
C17—C12—C13—C14	1.2 (4)	N6—C42—C43—C48	−153.4 (2)
C11—C12—C13—C14	179.7 (2)	C48—C43—C44—C45	−2.3 (4)
C12—C13—C14—C15	0.0 (5)	C42—C43—C44—C45	174.9 (2)
C13—C14—C15—C16	−1.5 (5)	C43—C44—C45—C46	0.9 (4)
C14—C15—C16—C17	1.9 (5)	C44—C45—C46—C47	1.3 (5)
C13—C12—C17—C16	−0.9 (4)	C45—C46—C47—C48	−2.0 (5)
C11—C12—C17—C16	−179.4 (2)	C46—C47—C48—C43	0.5 (5)
C15—C16—C17—C12	−0.7 (4)	C44—C43—C48—C47	1.7 (4)
C11—N3—C18—C19	−127.6 (2)	C42—C43—C48—C47	−175.7 (2)