(5,5-Diphenyl­hydantoinato-κN³)[tris­(3-amino­prop­yl)amine]copper(II) 5,5-diphenyl­hydantoinate methanol solvate

In the title compound, [Cu(C₁₅H₁₁N₂O₂)(C₉H₂₄N₄)](C₁₅H₁₁-N₂O₂)·CH₃OH, the Cu^II atom is coordinated in a distorted square-pyramidal coordination geometry. There are inter­molecular N—H...O and O—H...N hydrogen bonds, forming a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.014 Å
• R factor = 0.075
• wR factor = 0.252
• Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level C
RFACR01_ALERT_3_C  The value of the weighted R factor is > 0.25
            Weighted R factor given   0.252
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         46 Perc.
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.54 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C34
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C37
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N5
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         14
PLAT420_ALERT_2_C D-H Without Acceptor       N7     -   H7B    ...          ?
PLAT480_ALERT_4_C Long H...A H-Bond Reported H7B    ..  O1      ..       2.65 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  11 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
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 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

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

(5,5-Diphenylhydantoinato-κN³)[tris(3-aminopropyl)amine]copper(II) 5,5-diphenylhydantoinate methanol solvate

Crystal data

[Cu(C15H11N2O2)(C9H24N4)](C15H11N2O2)·CH4O	F(000) = 830
Mr = 786.42	Dx = 1.371 Mg m^−3
Triclinic, P1	Melting point: 455 K
a = 8.562 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 14.548 (5) Å	Cell parameters from 991 reflections
c = 17.323 (7) Å	θ = 2.4–17.9°
α = 66.200 (6)°	µ = 0.63 mm^−1
β = 85.955 (6)°	T = 298 K
γ = 75.000 (6)°	Block, blue
V = 1905.6 (12) Å^3	0.17 × 0.12 × 0.07 mm
Z = 2

Data collection

Siemens SMART CCD area-detector diffractometer	6630 independent reflections
Radiation source: fine-focus sealed tube	3034 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.066
φ and ω scans	θmax = 25.0°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→9
Tmin = 0.901, Tmax = 0.957	k = −17→13
10028 measured reflections	l = −20→20

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)] = 0.075	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.252	H-atom parameters constrained
S = 0.99	w = 1/σ^2(Fo^2)
6630 reflections	(Δ/σ)max < 0.001
487 parameters	Δρmax = 0.44 e Å^−3
0 restraints	Δρmin = −0.50 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	0.71544 (11)	0.75408 (7)	0.36917 (6)	0.0411 (3)
N1	0.6092 (7)	0.7772 (4)	0.4701 (3)	0.0371 (14)
N2	0.5025 (7)	0.8686 (4)	0.5480 (3)	0.0402 (15)
H2	0.4731	0.9211	0.5617	0.048*
N3	0.3468 (8)	0.8339 (5)	0.1719 (4)	0.0502 (17)
N4	0.4408 (8)	0.8791 (4)	0.0405 (4)	0.0458 (16)
H4	0.4818	0.9146	−0.0051	0.055*
N5	0.8577 (8)	0.6846 (5)	0.2950 (4)	0.0507 (17)
N6	0.6383 (9)	0.9089 (5)	0.2700 (4)	0.0545 (18)
H6A	0.5504	0.9123	0.2425	0.065*
H6B	0.6087	0.9550	0.2941	0.065*
N7	0.9221 (8)	0.7692 (5)	0.4080 (4)	0.0564 (18)
H7A	0.9708	0.8064	0.3628	0.068*
H7B	0.8973	0.8041	0.4417	0.068*
N8	0.5301 (8)	0.6974 (5)	0.3584 (4)	0.0529 (18)
H8A	0.4535	0.7084	0.3943	0.063*
H8B	0.4862	0.7325	0.3057	0.063*
O1	0.6235 (7)	0.9478 (4)	0.4267 (3)	0.0541 (15)
O2	0.5418 (8)	0.6248 (4)	0.5504 (3)	0.0660 (18)
O3	0.4201 (7)	0.9896 (4)	0.1069 (3)	0.0583 (16)
O4	0.3006 (7)	0.6773 (4)	0.1913 (4)	0.0627 (16)
O5	0.8208 (9)	0.1286 (5)	0.6960 (4)	0.087 (2)
H5	0.7607	0.1418	0.7312	0.130*
C1	0.5813 (9)	0.8703 (5)	0.4794 (4)	0.0380 (18)
C2	0.4715 (9)	0.7685 (5)	0.5976 (4)	0.0369 (18)
C3	0.5444 (10)	0.7128 (6)	0.5386 (5)	0.0423 (19)
C4	0.5648 (9)	0.7160 (6)	0.6825 (5)	0.0441 (19)
C5	0.6494 (10)	0.6148 (6)	0.7174 (5)	0.057 (2)
H5A	0.6533	0.5728	0.6882	0.069*
C6	0.7294 (12)	0.5729 (8)	0.7949 (7)	0.082 (3)
H6	0.7882	0.5038	0.8173	0.098*
C7	0.7211 (14)	0.6349 (12)	0.8389 (7)	0.094 (4)
H7	0.7719	0.6072	0.8920	0.113*
C8	0.6393 (14)	0.7352 (11)	0.8046 (7)	0.090 (3)
H8	0.6375	0.7768	0.8338	0.108*
C9	0.5582 (11)	0.7778 (7)	0.7277 (5)	0.059 (2)
H9	0.4996	0.8470	0.7058	0.071*
C10	0.2932 (9)	0.7730 (5)	0.6060 (5)	0.0412 (19)
C11	0.2356 (11)	0.6999 (6)	0.6733 (5)	0.053 (2)
H11	0.3084	0.6462	0.7143	0.063*
C12	0.0748 (13)	0.7053 (9)	0.6804 (7)	0.078 (3)
H12	0.0404	0.6541	0.7256	0.094*
C13	−0.0387 (13)	0.7840 (10)	0.6230 (8)	0.081 (3)
H13	−0.1487	0.7877	0.6292	0.097*
C14	0.0165 (13)	0.8568 (8)	0.5563 (8)	0.081 (3)
H14	−0.0566	0.9103	0.5154	0.098*
C15	0.1794 (12)	0.8514 (6)	0.5492 (6)	0.067 (3)
H15	0.2135	0.9028	0.5041	0.081*
C16	0.4028 (10)	0.9074 (6)	0.1063 (5)	0.046 (2)
C17	0.4034 (9)	0.7814 (5)	0.0567 (5)	0.0416 (19)
C18	0.3439 (9)	0.7555 (6)	0.1476 (5)	0.047 (2)
C19	0.5544 (10)	0.6953 (6)	0.0596 (4)	0.0431 (19)
C20	0.5433 (11)	0.5938 (6)	0.0876 (5)	0.060 (2)
H20	0.4440	0.5781	0.1025	0.072*
C21	0.6796 (14)	0.5160 (6)	0.0933 (6)	0.073 (3)
H21	0.6705	0.4480	0.1122	0.088*
C22	0.8257 (13)	0.5354 (9)	0.0722 (6)	0.073 (3)
H22	0.9166	0.4817	0.0770	0.088*
C23	0.8380 (12)	0.6355 (9)	0.0437 (6)	0.071 (3)
H23	0.9384	0.6497	0.0290	0.086*
C24	0.7037 (10)	0.7160 (7)	0.0362 (5)	0.054 (2)
H24	0.7137	0.7839	0.0156	0.065*
C25	0.2682 (9)	0.7972 (5)	−0.0042 (5)	0.0418 (19)
C26	0.1206 (10)	0.8608 (6)	−0.0029 (6)	0.057 (2)
H26	0.1040	0.8915	0.0358	0.068*
C27	−0.0030 (12)	0.8803 (7)	−0.0573 (7)	0.072 (3)
H27	−0.1034	0.9231	−0.0553	0.087*
C28	0.0225 (15)	0.8365 (8)	−0.1146 (7)	0.089 (3)
H28	−0.0621	0.8493	−0.1515	0.106*
C29	0.1672 (14)	0.7750 (7)	−0.1193 (7)	0.080 (3)
H29	0.1831	0.7474	−0.1600	0.096*
C30	0.2920 (11)	0.7534 (6)	−0.0631 (6)	0.061 (2)
H30	0.3915	0.7096	−0.0649	0.073*
C31	0.9303 (12)	0.7589 (7)	0.2254 (6)	0.075 (3)
H31A	0.9810	0.7247	0.1888	0.090*
H31B	1.0158	0.7724	0.2499	0.090*
C32	0.8219 (12)	0.8623 (7)	0.1706 (5)	0.074 (3)
H32A	0.8805	0.8938	0.1210	0.089*
H32B	0.7292	0.8493	0.1515	0.089*
C33	0.7604 (12)	0.9396 (7)	0.2088 (6)	0.066 (3)
H33A	0.8497	0.9457	0.2364	0.079*
H33B	0.7140	1.0070	0.1646	0.079*
C34	0.9868 (12)	0.5947 (7)	0.3484 (6)	0.077 (3)
H34A	1.0449	0.5604	0.3132	0.092*
H34B	0.9353	0.5457	0.3911	0.092*
C35	1.1102 (11)	0.6181 (7)	0.3927 (6)	0.071 (3)
H35A	1.1656	0.6649	0.3504	0.086*
H35B	1.1904	0.5541	0.4232	0.086*
C36	1.0354 (12)	0.6669 (7)	0.4544 (6)	0.070 (3)
H36A	0.9779	0.6215	0.4966	0.084*
H36B	1.1202	0.6757	0.4832	0.084*
C37	0.7598 (13)	0.6448 (9)	0.2543 (7)	0.083 (3)
H37A	0.8300	0.6165	0.2185	0.099*
H37B	0.6778	0.7036	0.2177	0.099*
C38	0.6764 (13)	0.5638 (7)	0.3102 (8)	0.084 (3)
H38A	0.6070	0.5525	0.2747	0.101*
H38B	0.7581	0.4992	0.3370	0.101*
C39	0.5785 (14)	0.5862 (7)	0.3763 (7)	0.081 (3)
H39A	0.6400	0.5493	0.4297	0.098*
H39B	0.4823	0.5609	0.3821	0.098*
C40	0.7975 (15)	0.0419 (10)	0.6893 (8)	0.113 (4)
H40A	0.8988	0.0018	0.6793	0.169*
H40B	0.7221	0.0628	0.6432	0.169*
H40C	0.7553	0.0006	0.7408	0.169*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0432 (6)	0.0456 (6)	0.0397 (6)	−0.0163 (4)	0.0135 (4)	−0.0212 (4)
N1	0.043 (4)	0.030 (3)	0.038 (4)	−0.007 (3)	0.009 (3)	−0.015 (3)
N2	0.062 (4)	0.028 (3)	0.034 (3)	−0.017 (3)	0.026 (3)	−0.017 (3)
N3	0.052 (5)	0.055 (4)	0.044 (4)	−0.014 (3)	0.017 (3)	−0.022 (3)
N4	0.053 (4)	0.046 (4)	0.046 (4)	−0.021 (3)	0.012 (3)	−0.022 (3)
N5	0.043 (4)	0.070 (5)	0.046 (4)	−0.011 (4)	0.004 (3)	−0.033 (4)
N6	0.066 (5)	0.051 (4)	0.049 (4)	−0.014 (3)	0.000 (4)	−0.021 (3)
N7	0.051 (5)	0.074 (5)	0.054 (4)	−0.025 (4)	0.015 (4)	−0.033 (4)
N8	0.051 (5)	0.070 (5)	0.056 (4)	−0.029 (4)	0.015 (3)	−0.038 (4)
O1	0.083 (4)	0.044 (3)	0.051 (3)	−0.036 (3)	0.039 (3)	−0.028 (3)
O2	0.111 (5)	0.040 (3)	0.059 (4)	−0.035 (3)	0.040 (3)	−0.029 (3)
O3	0.063 (4)	0.062 (4)	0.065 (4)	−0.017 (3)	0.006 (3)	−0.040 (3)
O4	0.063 (4)	0.053 (3)	0.059 (4)	−0.016 (3)	0.029 (3)	−0.014 (3)
O5	0.101 (6)	0.104 (5)	0.082 (5)	−0.048 (4)	0.044 (4)	−0.057 (4)
C1	0.045 (5)	0.037 (4)	0.037 (4)	−0.015 (4)	0.011 (4)	−0.019 (4)
C2	0.046 (5)	0.031 (4)	0.042 (4)	−0.017 (3)	0.016 (4)	−0.020 (3)
C3	0.054 (5)	0.040 (4)	0.038 (4)	−0.021 (4)	0.018 (4)	−0.018 (4)
C4	0.045 (5)	0.051 (5)	0.044 (5)	−0.023 (4)	0.015 (4)	−0.022 (4)
C5	0.059 (6)	0.055 (5)	0.049 (5)	−0.011 (4)	0.011 (5)	−0.015 (4)
C6	0.055 (7)	0.088 (7)	0.063 (7)	−0.009 (5)	0.004 (6)	0.004 (6)
C7	0.061 (8)	0.158 (12)	0.048 (7)	−0.034 (8)	0.003 (6)	−0.022 (8)
C8	0.083 (9)	0.143 (11)	0.058 (7)	−0.036 (8)	0.005 (6)	−0.051 (8)
C9	0.056 (6)	0.077 (6)	0.047 (5)	−0.021 (5)	0.008 (4)	−0.026 (5)
C10	0.043 (5)	0.041 (4)	0.043 (5)	−0.012 (4)	0.009 (4)	−0.019 (4)
C11	0.050 (6)	0.063 (5)	0.048 (5)	−0.027 (4)	0.013 (4)	−0.018 (4)
C12	0.070 (8)	0.108 (8)	0.088 (8)	−0.061 (7)	0.027 (6)	−0.050 (7)
C13	0.045 (7)	0.130 (10)	0.099 (9)	−0.037 (7)	0.028 (6)	−0.071 (8)
C14	0.049 (7)	0.089 (8)	0.108 (9)	−0.013 (6)	−0.007 (6)	−0.043 (7)
C15	0.063 (7)	0.054 (6)	0.075 (7)	−0.015 (5)	−0.001 (5)	−0.015 (5)
C16	0.042 (5)	0.053 (5)	0.042 (5)	−0.004 (4)	0.003 (4)	−0.022 (4)
C17	0.038 (5)	0.045 (4)	0.040 (4)	−0.012 (4)	0.006 (4)	−0.015 (4)
C18	0.034 (5)	0.048 (5)	0.051 (5)	0.002 (4)	0.000 (4)	−0.017 (4)
C19	0.046 (5)	0.048 (5)	0.030 (4)	−0.009 (4)	0.002 (4)	−0.013 (4)
C20	0.052 (6)	0.053 (5)	0.074 (6)	−0.013 (4)	0.020 (5)	−0.027 (5)
C21	0.100 (9)	0.040 (5)	0.060 (6)	0.008 (5)	0.008 (6)	−0.017 (4)
C22	0.053 (7)	0.092 (8)	0.056 (6)	0.021 (6)	0.000 (5)	−0.035 (6)
C23	0.055 (7)	0.110 (8)	0.054 (6)	−0.011 (6)	0.012 (5)	−0.046 (6)
C24	0.046 (6)	0.069 (6)	0.048 (5)	−0.016 (5)	0.006 (4)	−0.025 (4)
C25	0.042 (5)	0.036 (4)	0.049 (5)	−0.017 (4)	0.011 (4)	−0.015 (4)
C26	0.040 (5)	0.058 (5)	0.067 (6)	−0.003 (4)	0.002 (5)	−0.026 (5)
C27	0.046 (6)	0.069 (6)	0.078 (7)	−0.010 (5)	0.000 (6)	−0.007 (5)
C28	0.077 (9)	0.096 (8)	0.092 (9)	−0.022 (7)	−0.028 (7)	−0.032 (7)
C29	0.084 (8)	0.083 (7)	0.087 (8)	−0.003 (6)	−0.021 (7)	−0.056 (6)
C30	0.061 (6)	0.060 (5)	0.067 (6)	−0.009 (5)	0.003 (5)	−0.035 (5)
C31	0.072 (7)	0.085 (7)	0.056 (6)	−0.014 (6)	0.026 (5)	−0.023 (5)
C32	0.063 (7)	0.095 (7)	0.040 (5)	−0.011 (6)	0.018 (5)	−0.010 (5)
C33	0.066 (7)	0.064 (6)	0.060 (6)	−0.037 (5)	0.004 (5)	−0.004 (5)
C34	0.076 (7)	0.065 (6)	0.074 (7)	0.015 (5)	0.002 (6)	−0.032 (5)
C35	0.054 (6)	0.069 (6)	0.075 (7)	0.000 (5)	−0.007 (5)	−0.021 (5)
C36	0.069 (7)	0.082 (7)	0.052 (6)	−0.015 (5)	−0.004 (5)	−0.022 (5)
C37	0.073 (8)	0.116 (9)	0.077 (7)	−0.014 (6)	0.012 (6)	−0.063 (7)
C38	0.082 (8)	0.067 (7)	0.117 (9)	−0.005 (6)	−0.007 (7)	−0.059 (7)
C39	0.107 (9)	0.065 (6)	0.091 (8)	−0.047 (6)	0.000 (7)	−0.033 (6)
C40	0.108 (11)	0.130 (11)	0.101 (10)	−0.019 (8)	0.011 (8)	−0.056 (9)

Geometric parameters (Å, º)

Cu1—N8	2.019 (6)	C14—C15	1.376 (13)
Cu1—N1	2.023 (6)	C14—H14	0.9300
Cu1—N7	2.030 (6)	C15—H15	0.9300
Cu1—N5	2.086 (6)	C17—C25	1.532 (10)
Cu1—N6	2.174 (6)	C17—C19	1.537 (10)
N1—C3	1.368 (9)	C17—C18	1.545 (11)
N1—C1	1.385 (8)	C19—C20	1.384 (10)
N2—C1	1.320 (8)	C19—C24	1.385 (11)
N2—C2	1.446 (8)	C20—C21	1.376 (12)
N2—H2	0.8600	C20—H20	0.9300
N3—C16	1.367 (10)	C21—C22	1.347 (14)
N3—C18	1.373 (9)	C21—H21	0.9300
N4—C16	1.354 (9)	C22—C23	1.367 (13)
N4—C17	1.450 (8)	C22—H22	0.9300
N4—H4	0.8600	C23—C24	1.383 (12)
N5—C37	1.481 (11)	C23—H23	0.9300
N5—C31	1.483 (11)	C24—H24	0.9300
N5—C34	1.486 (10)	C25—C26	1.364 (10)
N6—C33	1.456 (11)	C25—C30	1.385 (10)
N6—H6A	0.9000	C26—C27	1.363 (12)
N6—H6B	0.9000	C26—H26	0.9300
N7—C36	1.483 (10)	C27—C28	1.359 (13)
N7—H7A	0.9000	C27—H27	0.9300
N7—H7B	0.9000	C28—C29	1.347 (14)
N8—C39	1.466 (10)	C28—H28	0.9300
N8—H8A	0.9000	C29—C30	1.383 (12)
N8—H8B	0.9000	C29—H29	0.9300
O1—C1	1.252 (8)	C30—H30	0.9300
O2—C3	1.218 (7)	C31—C32	1.507 (12)
O3—C16	1.247 (8)	C31—H31A	0.9700
O4—C18	1.219 (9)	C31—H31B	0.9700
O5—C40	1.376 (11)	C32—C33	1.492 (12)
O5—H5	0.8200	C32—H32A	0.9700
C2—C10	1.510 (10)	C32—H32B	0.9700
C2—C4	1.526 (10)	C33—H33A	0.9700
C2—C3	1.551 (10)	C33—H33B	0.9700
C4—C5	1.360 (10)	C34—C35	1.529 (12)
C4—C9	1.400 (10)	C34—H34A	0.9700
C5—C6	1.377 (12)	C34—H34B	0.9700
C5—H5A	0.9300	C35—C36	1.529 (12)
C6—C7	1.383 (14)	C35—H35A	0.9700
C6—H6	0.9300	C35—H35B	0.9700
C7—C8	1.342 (14)	C36—H36A	0.9700
C7—H7	0.9300	C36—H36B	0.9700
C8—C9	1.372 (12)	C37—C38	1.502 (14)
C8—H8	0.9300	C37—H37A	0.9700
C9—H9	0.9300	C37—H37B	0.9700
C10—C15	1.368 (10)	C38—C39	1.465 (13)
C10—C11	1.386 (10)	C38—H38A	0.9700
C11—C12	1.359 (12)	C38—H38B	0.9700
C11—H11	0.9300	C39—H39A	0.9700
C12—C13	1.373 (14)	C39—H39B	0.9700
C12—H12	0.9300	C40—H40A	0.9600
C13—C14	1.370 (14)	C40—H40B	0.9600
C13—H13	0.9300	C40—H40C	0.9600
N8—Cu1—N1	88.5 (2)	C19—C17—C18	107.9 (6)
N8—Cu1—N7	163.1 (3)	O4—C18—N3	125.0 (8)
N1—Cu1—N7	87.7 (2)	O4—C18—C17	125.3 (7)
N8—Cu1—N5	91.0 (3)	N3—C18—C17	109.7 (7)
N1—Cu1—N5	161.8 (2)	C20—C19—C24	118.4 (7)
N7—Cu1—N5	87.5 (3)	C20—C19—C17	119.8 (7)
N8—Cu1—N6	98.8 (3)	C24—C19—C17	121.8 (7)
N1—Cu1—N6	101.1 (2)	C21—C20—C19	120.0 (9)
N7—Cu1—N6	98.1 (3)	C21—C20—H20	120.0
N5—Cu1—N6	96.9 (3)	C19—C20—H20	120.0
C3—N1—C1	106.0 (6)	C22—C21—C20	121.9 (9)
C3—N1—Cu1	130.4 (5)	C22—C21—H21	119.1
C1—N1—Cu1	123.6 (5)	C20—C21—H21	119.1
C1—N2—C2	112.2 (5)	C21—C22—C23	118.8 (9)
C1—N2—H2	123.9	C21—C22—H22	120.6
C2—N2—H2	123.9	C23—C22—H22	120.6
C16—N3—C18	107.8 (7)	C22—C23—C24	121.1 (10)
C16—N4—C17	111.3 (6)	C22—C23—H23	119.4
C16—N4—H4	124.3	C24—C23—H23	119.4
C17—N4—H4	124.3	C23—C24—C19	119.9 (9)
C37—N5—C31	106.1 (7)	C23—C24—H24	120.1
C37—N5—C34	107.4 (7)	C19—C24—H24	120.1
C31—N5—C34	110.1 (7)	C26—C25—C30	118.8 (8)
C37—N5—Cu1	111.0 (5)	C26—C25—C17	118.6 (7)
C31—N5—Cu1	112.1 (5)	C30—C25—C17	122.6 (7)
C34—N5—Cu1	110.0 (5)	C27—C26—C25	121.3 (9)
C33—N6—Cu1	114.6 (5)	C27—C26—H26	119.4
C33—N6—H6A	108.6	C25—C26—H26	119.4
Cu1—N6—H6A	108.6	C28—C27—C26	119.2 (9)
C33—N6—H6B	108.6	C28—C27—H27	120.4
Cu1—N6—H6B	108.6	C26—C27—H27	120.4
H6A—N6—H6B	107.6	C29—C28—C27	121.5 (10)
C36—N7—Cu1	111.8 (5)	C29—C28—H28	119.2
C36—N7—H7A	109.3	C27—C28—H28	119.2
Cu1—N7—H7A	109.3	C28—C29—C30	119.5 (9)
C36—N7—H7B	109.3	C28—C29—H29	120.3
Cu1—N7—H7B	109.3	C30—C29—H29	120.3
H7A—N7—H7B	107.9	C29—C30—C25	119.8 (8)
C39—N8—Cu1	113.3 (6)	C29—C30—H30	120.1
C39—N8—H8A	108.9	C25—C30—H30	120.1
Cu1—N8—H8A	108.9	N5—C31—C32	118.5 (8)
C39—N8—H8B	108.9	N5—C31—H31A	107.7
Cu1—N8—H8B	108.9	C32—C31—H31A	107.7
H8A—N8—H8B	107.7	N5—C31—H31B	107.7
C40—O5—H5	109.5	C32—C31—H31B	107.7
O1—C1—N2	124.3 (6)	H31A—C31—H31B	107.1
O1—C1—N1	123.0 (7)	C33—C32—C31	117.6 (8)
N2—C1—N1	112.7 (6)	C33—C32—H32A	107.9
N2—C2—C10	112.9 (6)	C31—C32—H32A	107.9
N2—C2—C4	111.4 (6)	C33—C32—H32B	107.9
C10—C2—C4	112.9 (6)	C31—C32—H32B	107.9
N2—C2—C3	98.6 (5)	H32A—C32—H32B	107.2
C10—C2—C3	109.6 (6)	N6—C33—C32	111.0 (7)
C4—C2—C3	110.7 (6)	N6—C33—H33A	109.4
O2—C3—N1	124.4 (7)	C32—C33—H33A	109.4
O2—C3—C2	125.0 (6)	N6—C33—H33B	109.4
N1—C3—C2	110.5 (6)	C32—C33—H33B	109.4
C5—C4—C9	118.6 (8)	H33A—C33—H33B	108.0
C5—C4—C2	125.1 (7)	N5—C34—C35	116.8 (7)
C9—C4—C2	116.3 (7)	N5—C34—H34A	108.1
C4—C5—C6	121.6 (9)	C35—C34—H34A	108.1
C4—C5—H5A	119.2	N5—C34—H34B	108.1
C6—C5—H5A	119.2	C35—C34—H34B	108.1
C5—C6—C7	119.1 (10)	H34A—C34—H34B	107.3
C5—C6—H6	120.4	C34—C35—C36	113.6 (8)
C7—C6—H6	120.4	C34—C35—H35A	108.8
C8—C7—C6	119.7 (10)	C36—C35—H35A	108.8
C8—C7—H7	120.1	C34—C35—H35B	108.8
C6—C7—H7	120.1	C36—C35—H35B	108.8
C7—C8—C9	121.8 (11)	H35A—C35—H35B	107.7
C7—C8—H8	119.1	N7—C36—C35	109.8 (7)
C9—C8—H8	119.1	N7—C36—H36A	109.7
C8—C9—C4	119.2 (9)	C35—C36—H36A	109.7
C8—C9—H9	120.4	N7—C36—H36B	109.7
C4—C9—H9	120.4	C35—C36—H36B	109.7
C15—C10—C11	116.4 (8)	H36A—C36—H36B	108.2
C15—C10—C2	121.8 (7)	N5—C37—C38	118.1 (8)
C11—C10—C2	121.8 (7)	N5—C37—H37A	107.8
C12—C11—C10	121.1 (9)	C38—C37—H37A	107.8
C12—C11—H11	119.4	N5—C37—H37B	107.8
C10—C11—H11	119.4	C38—C37—H37B	107.8
C11—C12—C13	122.1 (10)	H37A—C37—H37B	107.1
C11—C12—H12	119.0	C39—C38—C37	116.6 (8)
C13—C12—H12	119.0	C39—C38—H38A	108.1
C14—C13—C12	117.3 (10)	C37—C38—H38A	108.1
C14—C13—H13	121.3	C39—C38—H38B	108.1
C12—C13—H13	121.3	C37—C38—H38B	108.1
C13—C14—C15	120.5 (10)	H38A—C38—H38B	107.3
C13—C14—H14	119.7	C38—C39—N8	112.6 (8)
C15—C14—H14	119.7	C38—C39—H39A	109.1
C10—C15—C14	122.4 (9)	N8—C39—H39A	109.1
C10—C15—H15	118.8	C38—C39—H39B	109.1
C14—C15—H15	118.8	N8—C39—H39B	109.1
O3—C16—N4	123.6 (7)	H39A—C39—H39B	107.8
O3—C16—N3	124.8 (8)	O5—C40—H40A	109.5
N4—C16—N3	111.6 (7)	O5—C40—H40B	109.5
N4—C17—C25	110.7 (6)	H40A—C40—H40B	109.5
N4—C17—C19	112.7 (6)	O5—C40—H40C	109.5
C25—C17—C19	113.8 (6)	H40A—C40—H40C	109.5
N4—C17—C18	99.5 (6)	H40B—C40—H40C	109.5
C25—C17—C18	111.3 (6)
N8—Cu1—N1—C3	46.8 (7)	C3—C2—C10—C11	96.0 (8)
N7—Cu1—N1—C3	−116.7 (7)	C15—C10—C11—C12	1.6 (12)
N5—Cu1—N1—C3	−41.8 (12)	C2—C10—C11—C12	179.6 (7)
N6—Cu1—N1—C3	145.5 (6)	C10—C11—C12—C13	−1.5 (14)
N8—Cu1—N1—C1	−129.6 (6)	C11—C12—C13—C14	1.4 (15)
N7—Cu1—N1—C1	66.9 (6)	C12—C13—C14—C15	−1.5 (16)
N5—Cu1—N1—C1	141.8 (8)	C11—C10—C15—C14	−1.7 (13)
N6—Cu1—N1—C1	−30.9 (6)	C2—C10—C15—C14	−179.7 (8)
N8—Cu1—N5—C37	11.0 (6)	C13—C14—C15—C10	1.8 (16)
N1—Cu1—N5—C37	99.3 (9)	C17—N4—C16—O3	−178.3 (7)
N7—Cu1—N5—C37	174.2 (6)	C17—N4—C16—N3	2.9 (9)
N6—Cu1—N5—C37	−88.0 (6)	C18—N3—C16—O3	179.7 (7)
N8—Cu1—N5—C31	129.5 (6)	C18—N3—C16—N4	−1.6 (9)
N1—Cu1—N5—C31	−142.2 (8)	C16—N4—C17—C25	114.4 (7)
N7—Cu1—N5—C31	−67.4 (6)	C16—N4—C17—C19	−116.9 (7)
N6—Cu1—N5—C31	30.5 (6)	C16—N4—C17—C18	−2.8 (7)
N8—Cu1—N5—C34	−107.7 (6)	C16—N3—C18—O4	179.8 (8)
N1—Cu1—N5—C34	−19.4 (11)	C16—N3—C18—C17	−0.3 (8)
N7—Cu1—N5—C34	55.5 (6)	N4—C17—C18—O4	−178.3 (7)
N6—Cu1—N5—C34	153.3 (6)	C25—C17—C18—O4	65.0 (10)
N8—Cu1—N6—C33	−127.9 (6)	C19—C17—C18—O4	−60.5 (10)
N1—Cu1—N6—C33	141.8 (6)	N4—C17—C18—N3	1.9 (7)
N7—Cu1—N6—C33	52.6 (6)	C25—C17—C18—N3	−114.9 (7)
N5—Cu1—N6—C33	−35.9 (6)	C19—C17—C18—N3	119.6 (7)
N8—Cu1—N7—C36	22.3 (12)	N4—C17—C19—C20	169.7 (7)
N1—Cu1—N7—C36	99.5 (5)	C25—C17—C19—C20	−63.1 (9)
N5—Cu1—N7—C36	−62.9 (6)	C18—C17—C19—C20	60.9 (9)
N6—Cu1—N7—C36	−159.6 (5)	N4—C17—C19—C24	−9.1 (10)
N1—Cu1—N8—C39	−112.9 (6)	C25—C17—C19—C24	118.0 (8)
N7—Cu1—N8—C39	−35.8 (12)	C18—C17—C19—C24	−117.9 (8)
N5—Cu1—N8—C39	48.9 (6)	C24—C19—C20—C21	1.3 (12)
N6—Cu1—N8—C39	146.1 (6)	C17—C19—C20—C21	−177.5 (8)
C2—N2—C1—O1	−179.3 (7)	C19—C20—C21—C22	0.0 (14)
C2—N2—C1—N1	2.3 (9)	C20—C21—C22—C23	−0.6 (15)
C3—N1—C1—O1	−179.1 (7)	C21—C22—C23—C24	−0.1 (14)
Cu1—N1—C1—O1	−1.9 (10)	C22—C23—C24—C19	1.4 (13)
C3—N1—C1—N2	−0.7 (8)	C20—C19—C24—C23	−2.0 (12)
Cu1—N1—C1—N2	176.5 (5)	C17—C19—C24—C23	176.9 (7)
C1—N2—C2—C10	−118.2 (7)	N4—C17—C25—C26	−61.1 (9)
C1—N2—C2—C4	113.6 (7)	C19—C17—C25—C26	170.7 (7)
C1—N2—C2—C3	−2.6 (8)	C18—C17—C25—C26	48.5 (9)
C1—N1—C3—O2	177.5 (8)	N4—C17—C25—C30	115.8 (8)
Cu1—N1—C3—O2	0.6 (12)	C19—C17—C25—C30	−12.3 (10)
C1—N1—C3—C2	−1.1 (8)	C18—C17—C25—C30	−134.5 (8)
Cu1—N1—C3—C2	−178.0 (5)	C30—C25—C26—C27	1.0 (12)
N2—C2—C3—O2	−176.4 (8)	C17—C25—C26—C27	178.1 (8)
C10—C2—C3—O2	−58.3 (10)	C25—C26—C27—C28	−0.9 (14)
C4—C2—C3—O2	66.8 (10)	C26—C27—C28—C29	−0.5 (17)
N2—C2—C3—N1	2.2 (8)	C27—C28—C29—C30	1.8 (17)
C10—C2—C3—N1	120.3 (7)	C28—C29—C30—C25	−1.7 (15)
C4—C2—C3—N1	−114.6 (7)	C26—C25—C30—C29	0.3 (13)
N2—C2—C4—C5	−134.7 (8)	C17—C25—C30—C29	−176.7 (8)
C10—C2—C4—C5	97.1 (9)	C37—N5—C31—C32	72.0 (10)
C3—C2—C4—C5	−26.1 (10)	C34—N5—C31—C32	−172.1 (8)
N2—C2—C4—C9	46.7 (9)	Cu1—N5—C31—C32	−49.3 (10)
C10—C2—C4—C9	−81.5 (8)	N5—C31—C32—C33	71.5 (12)
C3—C2—C4—C9	155.3 (7)	Cu1—N6—C33—C32	54.7 (8)
C9—C4—C5—C6	−0.8 (13)	C31—C32—C33—N6	−72.2 (11)
C2—C4—C5—C6	−179.4 (8)	C37—N5—C34—C35	176.4 (8)
C4—C5—C6—C7	1.1 (15)	C31—N5—C34—C35	61.2 (10)
C5—C6—C7—C8	−1.8 (17)	Cu1—N5—C34—C35	−62.8 (9)
C6—C7—C8—C9	2.2 (18)	N5—C34—C35—C36	61.2 (11)
C7—C8—C9—C4	−1.9 (16)	Cu1—N7—C36—C35	72.6 (8)
C5—C4—C9—C8	1.2 (13)	C34—C35—C36—N7	−63.1 (10)
C2—C4—C9—C8	179.9 (8)	C31—N5—C37—C38	177.5 (9)
N2—C2—C10—C15	22.7 (10)	C34—N5—C37—C38	59.8 (11)
C4—C2—C10—C15	150.1 (7)	Cu1—N5—C37—C38	−60.4 (10)
C3—C2—C10—C15	−86.1 (8)	N5—C37—C38—C39	50.8 (13)
N2—C2—C10—C11	−155.2 (7)	C37—C38—C39—N8	21.0 (13)
C4—C2—C10—C11	−27.8 (10)	Cu1—N8—C39—C38	−70.9 (9)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1^i	0.86	1.96	2.807 (7)	169
N4—H4···O3^ii	0.86	2.04	2.898 (9)	173
N6—H6A···O3	0.90	2.37	3.129 (8)	142
N6—H6B···O1	0.90	2.27	2.975 (8)	135
N7—H7A···O5^iii	0.90	2.23	3.046 (10)	151
N7—H7B···O1	0.90	2.65	3.243 (8)	124
N8—H8A···O2	0.90	2.55	3.056 (9)	116
N8—H8B···N3	0.90	2.39	3.282 (9)	174
O5—H5···N3^iv	0.82	1.97	2.782 (9)	170

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+1, −y+2, −z; (iii) −x+2, −y+1, −z+1; (iv) −x+1, −y+1, −z+1.