Aqua­bis[3-ethyl-4-(4-methyl­phen­yl)-5-(2-pyrid­yl)-4H-1,2,4-triazole-κ²N,N′]copper(II) disalicylate dihydrate

In the title complex, [Cu(C₁₆H₁₆N₄)₂(H₂O)](C₇H₅O₃)₂·2H₂O, the Cu^II atom is in a slightly distorted square-pyramidal coordination geometry. In the crystal structure, inter­molecular O—H...O hydrogen bonds form centrosymmetric clusters.

Key indicators

• Single-crystal X-ray study
• T = 571 K
• Mean [sigma](C-C)= 0.006 Å
• R factor = 0.060
• wR factor = 0.145
• Data-to-parameter ratio = 15.1

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Aquabis[3-ethyl-4-(4-methylphenyl)-5-(2-pyridyl)-4H-1,2,4-triazole- κ²N,N']copper(II) disalicylate dihydrate

Crystal data

[Cu(C16H16N4)2(H2O)](C7H5O3)2·2H2O	Z = 2
Mr = 920.46	F(000) = 962
Triclinic, P1	Dx = 1.374 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.076 (9) Å	Cell parameters from 2959 reflections
b = 12.845 (11) Å	θ = 2.3–22.7°
c = 18.337 (16) Å	µ = 0.56 mm^−1
α = 106.716 (11)°	T = 571 K
β = 100.195 (12)°	Block, blue
γ = 92.669 (14)°	0.28 × 0.24 × 0.22 mm
V = 2225 (3) Å^3

Data collection

Bruker SMART APEX CCD diffractometer	8763 independent reflections
Radiation source: sealed tube	7180 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
φ and ω scans	θmax = 26.0°, θmin = 1.2°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −12→12
Tmin = 0.860, Tmax = 0.887	k = −15→15
20846 measured reflections	l = −22→22

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.145	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.07P)^2 + 1.99P] where P = (Fo^2 + 2Fc^2)/3
8763 reflections	(Δ/σ)max < 0.001
581 parameters	Δρmax = 0.29 e Å^−3
0 restraints	Δρmin = −0.51 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
C1	0.8337 (4)	0.5208 (3)	0.8494 (2)	0.0470 (9)
H1	0.7731	0.5657	0.8722	0.056*
C2	0.9218 (4)	0.4709 (3)	0.8938 (2)	0.0487 (9)
H2	0.9175	0.4811	0.9456	0.058*
C3	1.0123 (4)	0.4087 (4)	0.8620 (2)	0.0543 (10)
H3	1.0734	0.3787	0.8925	0.065*
C4	1.0151 (4)	0.3885 (3)	0.7827 (2)	0.0445 (8)
H4	1.0762	0.3448	0.7593	0.053*
C5	0.9221 (3)	0.4373 (2)	0.74121 (18)	0.0331 (7)
C6	0.9023 (3)	0.4231 (2)	0.65811 (18)	0.0320 (6)
C7	0.9014 (4)	0.3816 (3)	0.5341 (2)	0.0449 (8)
C8	0.9518 (4)	0.3458 (3)	0.4584 (2)	0.0517 (10)
H8E	0.9230	0.3925	0.4265	0.062*
H8F	1.0500	0.3502	0.4685	0.062*
C9	0.8919 (4)	0.2298 (3)	0.4176 (2)	0.0516 (9)
H9A	0.8057	0.2183	0.4311	0.077*
H9B	0.9519	0.1808	0.4332	0.077*
H9C	0.8797	0.2163	0.3624	0.077*
C10	1.0561 (4)	0.2815 (3)	0.6064 (2)	0.0413 (8)
C11	1.0072 (4)	0.1743 (3)	0.5945 (2)	0.0442 (8)
H11	0.9146	0.1546	0.5863	0.053*
C12	1.0973 (4)	0.0969 (3)	0.5949 (2)	0.0444 (8)
H12	1.0647	0.0248	0.5868	0.053*
C13	1.2369 (4)	0.1250 (3)	0.6074 (2)	0.0448 (8)
C14	1.2828 (4)	0.2348 (3)	0.6218 (2)	0.0441 (8)
H14	1.3754	0.2563	0.6329	0.053*
C15	1.1912 (4)	0.3124 (3)	0.6196 (2)	0.0469 (9)
H15	1.2223	0.3847	0.6272	0.056*
C16	1.3375 (4)	0.0436 (3)	0.6092 (2)	0.0485 (9)
H16A	1.2926	−0.0240	0.6092	0.073*
H16B	1.4067	0.0710	0.6553	0.073*
H16C	1.3781	0.0314	0.5642	0.073*
C17	0.6010 (4)	0.6230 (3)	0.55330 (19)	0.0420 (8)
H17	0.6376	0.5612	0.5274	0.050*
C18	0.5298 (4)	0.6815 (3)	0.5111 (2)	0.0463 (8)
H18	0.5188	0.6602	0.4572	0.056*
C19	0.4742 (4)	0.7731 (3)	0.5497 (2)	0.0506 (9)
H19	0.4275	0.8148	0.5218	0.061*
C20	0.4882 (4)	0.8027 (3)	0.6299 (2)	0.0437 (8)
H20	0.4490	0.8624	0.6567	0.052*
C21	0.5632 (3)	0.7395 (2)	0.66871 (17)	0.0328 (7)
C22	0.5881 (4)	0.7577 (2)	0.75238 (17)	0.0342 (7)
C23	0.6061 (4)	0.8064 (3)	0.87813 (19)	0.0427 (8)
C24	0.5993 (4)	0.8680 (3)	0.9592 (2)	0.0447 (8)
H24A	0.5911	0.8175	0.9890	0.054*
H24B	0.5202	0.9083	0.9593	0.054*
C25	0.7290 (5)	0.9483 (4)	0.9966 (2)	0.0610 (11)
H25A	0.8073	0.9090	0.9917	0.091*
H25B	0.7291	0.9822	1.0506	0.091*
H25C	0.7310	1.0034	0.9708	0.091*
C26	0.4598 (3)	0.9162 (3)	0.80950 (19)	0.0359 (7)
C27	0.3258 (4)	0.8886 (3)	0.7832 (2)	0.0413 (8)
H27	0.2901	0.8157	0.7656	0.050*
C28	0.2423 (4)	0.9707 (3)	0.7828 (2)	0.0439 (8)
H28	0.1496	0.9526	0.7637	0.053*
C29	0.2947 (4)	1.0800 (3)	0.8106 (2)	0.0500 (9)
C30	0.4287 (4)	1.1052 (3)	0.8349 (2)	0.0437 (8)
H30	0.4647	1.1780	0.8511	0.052*
C31	0.5149 (4)	1.0241 (3)	0.8363 (2)	0.0445 (8)
H31	0.6076	1.0421	0.8549	0.053*
C32	0.1998 (4)	1.1701 (3)	0.8122 (2)	0.0509 (9)
H32A	0.1649	1.1863	0.8593	0.076*
H32B	0.1259	1.1457	0.7683	0.076*
H32C	0.2490	1.2346	0.8102	0.076*
C33	0.6736 (4)	0.2255 (4)	0.7224 (3)	0.0553 (10)
C34	0.7392 (4)	0.1213 (3)	0.7168 (2)	0.0506 (9)
C35	0.7998 (4)	0.0994 (4)	0.7843 (3)	0.0567 (10)
H35A	0.8023	0.1501	0.8325	0.068*
C36	0.8569 (4)	0.0019 (3)	0.7798 (3)	0.0542 (10)
H36A	0.8974	−0.0128	0.8250	0.065*
C37	0.8532 (4)	−0.0739 (3)	0.7078 (3)	0.0556 (10)
H37A	0.8914	−0.1392	0.7048	0.067*
C38	0.7926 (4)	−0.0520 (4)	0.6403 (3)	0.0572 (10)
H38A	0.7901	−0.1027	0.5921	0.069*
C39	0.7355 (4)	0.0455 (3)	0.6448 (3)	0.0541 (10)
C40	0.2705 (4)	0.5883 (3)	0.7703 (2)	0.0485 (9)
C41	0.2171 (4)	0.6488 (3)	0.8387 (2)	0.0482 (9)
C42	0.2851 (4)	0.6554 (3)	0.9144 (2)	0.0555 (10)
H42	0.3650	0.6227	0.9210	0.067*
C43	0.2347 (4)	0.7096 (4)	0.9787 (3)	0.0559 (10)
H43	0.2792	0.7124	1.0282	0.067*
C44	0.1189 (4)	0.7590 (3)	0.9687 (2)	0.0539 (10)
H44	0.0865	0.7966	1.0123	0.065*
C45	0.0472 (4)	0.7552 (3)	0.8952 (2)	0.0547 (10)
H45	−0.0332	0.7876	0.8897	0.066*
C46	0.1004 (5)	0.7005 (3)	0.8293 (2)	0.0571 (10)
Cu1	0.71794 (4)	0.57006 (3)	0.70197 (2)	0.02994 (12)
N1	0.8362 (3)	0.5040 (2)	0.77351 (15)	0.0338 (6)
N2	0.8183 (3)	0.4784 (2)	0.62775 (15)	0.0343 (6)
N3	0.8173 (3)	0.4530 (3)	0.54870 (16)	0.0448 (7)
N4	0.9612 (3)	0.3596 (2)	0.60168 (16)	0.0398 (6)
N5	0.6200 (3)	0.6524 (2)	0.63201 (14)	0.0330 (6)
N6	0.6671 (3)	0.6933 (2)	0.78084 (15)	0.0377 (6)
N7	0.6776 (3)	0.7230 (2)	0.85998 (15)	0.0418 (7)
N8	0.5495 (3)	0.8320 (2)	0.81188 (15)	0.0364 (6)
O1	0.5402 (2)	0.4538 (2)	0.68227 (14)	0.0429 (6)
H1C	0.5121	0.4621	0.7244	0.052*
H1A	0.5607	0.3914	0.6664	0.052*
O2	0.6365 (3)	0.2491 (2)	0.66578 (18)	0.0620 (8)
O3	0.6659 (3)	0.2816 (2)	0.79184 (17)	0.0551 (7)
O4	0.6786 (3)	0.0826 (2)	0.58904 (14)	0.0470 (6)
H4A	0.6724	0.1483	0.6054	0.056*
O5	0.3751 (3)	0.5399 (2)	0.77801 (16)	0.0525 (6)
O6	0.2068 (3)	0.5887 (2)	0.70264 (15)	0.0516 (6)
O7	0.0338 (3)	0.6981 (2)	0.75855 (16)	0.0507 (6)
H7	0.0695	0.6591	0.7253	0.061*
O8	0.5168 (3)	0.4298 (2)	0.87421 (13)	0.0483 (6)
H8A	0.4551	0.4558	0.8488	0.058*
H8B	0.5050	0.3604	0.8577	0.058*
O9	0.3455 (3)	0.3907 (2)	0.98223 (17)	0.0574 (7)
H9F	0.3941	0.4018	0.9512	0.069*
H9E	0.3421	0.4507	1.0166	0.069*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.061 (2)	0.055 (2)	0.0317 (17)	0.0134 (18)	0.0147 (16)	0.0197 (16)
C2	0.048 (2)	0.065 (2)	0.0324 (17)	0.0125 (18)	−0.0002 (15)	0.0175 (17)
C3	0.046 (2)	0.064 (3)	0.047 (2)	0.0108 (19)	−0.0017 (17)	0.0130 (19)
C4	0.0381 (19)	0.045 (2)	0.049 (2)	0.0104 (15)	−0.0003 (16)	0.0174 (16)
C5	0.0344 (17)	0.0297 (15)	0.0320 (16)	0.0040 (13)	0.0032 (13)	0.0063 (12)
C6	0.0347 (17)	0.0262 (14)	0.0323 (16)	0.0017 (12)	0.0075 (13)	0.0043 (12)
C7	0.0398 (19)	0.062 (2)	0.0363 (18)	0.0125 (17)	0.0060 (15)	0.0195 (16)
C8	0.055 (2)	0.050 (2)	0.047 (2)	0.0242 (19)	0.0108 (18)	0.0058 (17)
C9	0.047 (2)	0.055 (2)	0.052 (2)	0.0004 (18)	0.0064 (17)	0.0164 (18)
C10	0.050 (2)	0.0350 (17)	0.0393 (18)	0.0175 (15)	0.0115 (15)	0.0082 (14)
C11	0.045 (2)	0.0369 (18)	0.048 (2)	0.0046 (15)	0.0104 (16)	0.0085 (15)
C12	0.044 (2)	0.0331 (17)	0.060 (2)	0.0039 (15)	0.0109 (17)	0.0184 (16)
C13	0.051 (2)	0.0425 (19)	0.0426 (19)	0.0135 (16)	0.0153 (16)	0.0114 (15)
C14	0.045 (2)	0.0424 (19)	0.0426 (19)	0.0081 (16)	0.0051 (16)	0.0106 (15)
C15	0.050 (2)	0.0349 (18)	0.052 (2)	0.0089 (16)	0.0048 (17)	0.0094 (16)
C16	0.050 (2)	0.050 (2)	0.048 (2)	0.0122 (17)	0.0198 (17)	0.0123 (17)
C17	0.047 (2)	0.048 (2)	0.0301 (16)	0.0080 (16)	0.0055 (14)	0.0102 (14)
C18	0.052 (2)	0.053 (2)	0.0351 (18)	0.0136 (17)	0.0110 (16)	0.0138 (16)
C19	0.045 (2)	0.056 (2)	0.050 (2)	0.0142 (18)	0.0171 (17)	0.0096 (18)
C20	0.044 (2)	0.047 (2)	0.0426 (19)	0.0139 (16)	0.0099 (16)	0.0157 (16)
C21	0.0470 (19)	0.0232 (14)	0.0271 (15)	0.0052 (13)	0.0070 (13)	0.0057 (12)
C22	0.050 (2)	0.0240 (14)	0.0276 (15)	0.0127 (13)	0.0087 (14)	0.0041 (12)
C23	0.055 (2)	0.0435 (19)	0.0264 (16)	0.0130 (16)	0.0085 (15)	0.0038 (14)
C24	0.042 (2)	0.044 (2)	0.0425 (19)	0.0082 (16)	0.0155 (16)	0.0009 (15)
C25	0.061 (3)	0.060 (3)	0.043 (2)	−0.015 (2)	0.0086 (19)	−0.0113 (18)
C26	0.0429 (19)	0.0281 (15)	0.0350 (16)	0.0090 (13)	0.0087 (14)	0.0056 (13)
C27	0.043 (2)	0.0444 (19)	0.0415 (18)	0.0072 (15)	0.0150 (15)	0.0160 (15)
C28	0.042 (2)	0.047 (2)	0.0436 (19)	0.0138 (16)	0.0180 (16)	0.0078 (16)
C29	0.060 (3)	0.044 (2)	0.049 (2)	0.0139 (18)	0.0210 (18)	0.0110 (17)
C30	0.048 (2)	0.0314 (17)	0.053 (2)	0.0113 (15)	0.0181 (17)	0.0087 (15)
C31	0.057 (2)	0.0236 (15)	0.052 (2)	0.0076 (15)	0.0154 (17)	0.0077 (14)
C32	0.058 (2)	0.0376 (19)	0.056 (2)	0.0167 (17)	0.0129 (19)	0.0089 (17)
C33	0.049 (2)	0.057 (2)	0.055 (2)	−0.0131 (19)	0.0072 (19)	0.015 (2)
C34	0.046 (2)	0.051 (2)	0.053 (2)	−0.0050 (17)	0.0113 (18)	0.0150 (18)
C35	0.043 (2)	0.064 (3)	0.059 (2)	−0.0007 (19)	0.0065 (18)	0.016 (2)
C36	0.047 (2)	0.059 (2)	0.058 (2)	0.0125 (19)	0.0159 (19)	0.016 (2)
C37	0.057 (2)	0.046 (2)	0.064 (3)	0.0108 (18)	0.022 (2)	0.0103 (19)
C38	0.053 (2)	0.058 (2)	0.053 (2)	−0.0050 (19)	0.0194 (19)	0.0011 (19)
C39	0.047 (2)	0.055 (2)	0.064 (3)	−0.0023 (18)	0.0146 (19)	0.023 (2)
C40	0.057 (2)	0.042 (2)	0.051 (2)	0.0002 (17)	0.0136 (18)	0.0194 (17)
C41	0.060 (2)	0.0376 (19)	0.047 (2)	−0.0034 (17)	0.0109 (18)	0.0148 (16)
C42	0.052 (2)	0.058 (2)	0.045 (2)	−0.0063 (19)	0.0076 (18)	−0.0006 (18)
C43	0.049 (2)	0.062 (3)	0.056 (2)	0.0109 (19)	0.0133 (19)	0.013 (2)
C44	0.045 (2)	0.050 (2)	0.050 (2)	−0.0029 (17)	0.0131 (18)	−0.0120 (17)
C45	0.046 (2)	0.047 (2)	0.065 (3)	0.0020 (17)	0.0152 (19)	0.0033 (19)
C46	0.058 (3)	0.049 (2)	0.053 (2)	−0.0089 (19)	0.0021 (19)	0.0053 (18)
Cu1	0.0423 (2)	0.02591 (19)	0.02282 (18)	0.01471 (15)	0.00702 (15)	0.00713 (14)
N1	0.0375 (15)	0.0331 (14)	0.0331 (13)	0.0130 (11)	0.0077 (11)	0.0115 (11)
N2	0.0400 (15)	0.0336 (14)	0.0278 (13)	0.0098 (12)	0.0095 (11)	0.0045 (11)
N3	0.0429 (17)	0.0593 (19)	0.0305 (14)	0.0108 (14)	0.0109 (12)	0.0078 (13)
N4	0.0416 (16)	0.0431 (16)	0.0367 (15)	0.0131 (13)	0.0153 (12)	0.0091 (12)
N5	0.0427 (15)	0.0289 (13)	0.0262 (12)	0.0133 (11)	0.0061 (11)	0.0057 (10)
N6	0.0532 (18)	0.0322 (14)	0.0292 (13)	0.0140 (12)	0.0116 (12)	0.0080 (11)
N7	0.0485 (17)	0.0485 (17)	0.0244 (13)	0.0118 (14)	0.0087 (12)	0.0030 (12)
N8	0.0458 (16)	0.0330 (14)	0.0343 (14)	0.0100 (12)	0.0175 (12)	0.0093 (11)
O1	0.0422 (14)	0.0432 (13)	0.0389 (13)	0.0019 (11)	0.0103 (10)	0.0045 (10)
O2	0.0539 (17)	0.0552 (17)	0.0628 (19)	−0.0094 (13)	−0.0151 (14)	0.0140 (14)
O3	0.0486 (16)	0.0492 (15)	0.0608 (17)	0.0064 (12)	0.0125 (13)	0.0051 (13)
O4	0.0612 (17)	0.0389 (13)	0.0449 (14)	0.0142 (12)	0.0193 (12)	0.0121 (11)
O5	0.0518 (16)	0.0500 (15)	0.0566 (16)	0.0114 (13)	0.0140 (13)	0.0144 (13)
O6	0.0524 (16)	0.0606 (17)	0.0448 (14)	0.0115 (13)	0.0126 (12)	0.0178 (13)
O7	0.0508 (16)	0.0496 (15)	0.0530 (15)	0.0133 (12)	0.0129 (12)	0.0144 (12)
O8	0.0598 (16)	0.0515 (15)	0.0332 (12)	0.0207 (12)	0.0093 (11)	0.0097 (11)
O9	0.0565 (17)	0.0600 (17)	0.0574 (17)	0.0113 (14)	0.0206 (14)	0.0139 (14)

Geometric parameters (Å, º)

C1—N1	1.350 (4)	C26—C27	1.345 (5)
C1—C2	1.399 (5)	C26—C31	1.383 (5)
C1—H1	0.9300	C26—N8	1.446 (4)
C2—C3	1.341 (6)	C27—C28	1.380 (5)
C2—H2	0.9300	C27—H27	0.9300
C3—C4	1.409 (6)	C28—C29	1.391 (6)
C3—H3	0.9300	C28—H28	0.9300
C4—C5	1.388 (5)	C29—C30	1.338 (6)
C4—H4	0.9300	C29—C32	1.532 (5)
C5—N1	1.339 (4)	C30—C31	1.389 (5)
C5—C6	1.458 (4)	C30—H30	0.9300
C6—N2	1.283 (4)	C31—H31	0.9300
C6—N4	1.366 (4)	C32—H32A	0.9600
C7—N3	1.282 (5)	C32—H32B	0.9600
C7—N4	1.391 (4)	C32—H32C	0.9600
C7—C8	1.516 (5)	C33—O2	1.168 (5)
C8—C9	1.504 (6)	C33—O3	1.287 (5)
C8—H8E	0.9700	C33—C34	1.506 (6)
C8—H8F	0.9700	C34—C35	1.390 (6)
C9—H9A	0.9600	C34—C39	1.390 (6)
C9—H9B	0.9600	C35—C36	1.390 (6)
C9—H9C	0.9600	C35—H35A	0.9300
C10—C15	1.359 (6)	C36—C37	1.390 (6)
C10—C11	1.383 (5)	C36—H36A	0.9300
C10—N4	1.427 (4)	C37—C38	1.390 (6)
C11—C12	1.378 (5)	C37—H37A	0.9300
C11—H11	0.9300	C38—C39	1.390 (6)
C12—C13	1.397 (6)	C38—H38A	0.9300
C12—H12	0.9300	C39—O4	1.304 (5)
C13—C14	1.398 (5)	C40—O5	1.256 (5)
C13—C16	1.493 (5)	C40—O6	1.293 (5)
C14—C15	1.393 (5)	C40—C41	1.478 (6)
C14—H14	0.9300	C41—C46	1.386 (6)
C15—H15	0.9300	C41—C42	1.412 (6)
C16—H16A	0.9600	C42—C43	1.380 (6)
C16—H16B	0.9600	C42—H42	0.9300
C16—H16C	0.9600	C43—C44	1.363 (6)
C17—N5	1.358 (4)	C43—H43	0.9300
C17—C18	1.367 (5)	C44—C45	1.398 (6)
C17—H17	0.9300	C44—H44	0.9300
C18—C19	1.387 (5)	C45—C46	1.421 (6)
C18—H18	0.9300	C45—H45	0.9300
C19—C20	1.389 (5)	C46—O7	1.342 (5)
C19—H19	0.9300	Cu1—N6	1.970 (3)
C20—C21	1.391 (5)	Cu1—N2	1.984 (3)
C20—H20	0.9300	Cu1—N1	2.011 (3)
C21—N5	1.339 (4)	Cu1—N5	2.042 (3)
C21—C22	1.457 (4)	Cu1—O1	2.186 (3)
C22—N6	1.324 (4)	N2—N3	1.389 (4)
C22—N8	1.356 (4)	N6—N7	1.373 (4)
C23—N7	1.315 (4)	O1—H1C	0.8500
C23—N8	1.382 (4)	O1—H1A	0.8200
C23—C24	1.485 (5)	O4—H4A	0.8200
C24—C25	1.547 (5)	O7—H7	0.8200
C24—H24A	0.9700	O8—H8A	0.8500
C24—H24B	0.9700	O8—H8B	0.8500
C25—H25A	0.9600	O9—H9F	0.8500
C25—H25B	0.9600	O9—H9E	0.8500
C25—H25C	0.9600
N1—C1—C2	120.3 (3)	C27—C28—H28	119.5
N1—C1—H1	119.8	C29—C28—H28	119.5
C2—C1—H1	119.8	C30—C29—C28	119.1 (3)
C3—C2—C1	120.3 (4)	C30—C29—C32	120.7 (4)
C3—C2—H2	119.9	C28—C29—C32	120.2 (4)
C1—C2—H2	119.9	C29—C30—C31	121.0 (4)
C2—C3—C4	120.3 (4)	C29—C30—H30	119.5
C2—C3—H3	119.8	C31—C30—H30	119.5
C4—C3—H3	119.8	C26—C31—C30	118.6 (4)
C5—C4—C3	116.5 (3)	C26—C31—H31	120.7
C5—C4—H4	121.7	C30—C31—H31	120.7
C3—C4—H4	121.7	C29—C32—H32A	109.5
N1—C5—C4	123.4 (3)	C29—C32—H32B	109.5
N1—C5—C6	110.7 (3)	H32A—C32—H32B	109.5
C4—C5—C6	125.9 (3)	C29—C32—H32C	109.5
N2—C6—N4	109.1 (3)	H32A—C32—H32C	109.5
N2—C6—C5	119.5 (3)	H32B—C32—H32C	109.5
N4—C6—C5	131.4 (3)	O2—C33—O3	126.2 (5)
N3—C7—N4	110.4 (3)	O2—C33—C34	119.0 (4)
N3—C7—C8	124.3 (3)	O3—C33—C34	114.7 (4)
N4—C7—C8	124.0 (3)	C35—C34—C39	120.0 (4)
C9—C8—C7	106.9 (4)	C35—C34—C33	119.6 (4)
C9—C8—H8E	110.3	C39—C34—C33	120.4 (4)
C7—C8—H8E	110.3	C34—C35—C36	120.0 (4)
C9—C8—H8F	110.3	C34—C35—H35A	120.0
C7—C8—H8F	110.3	C36—C35—H35A	120.0
H8E—C8—H8F	108.6	C37—C36—C35	120.0 (4)
C8—C9—H9A	109.5	C37—C36—H36A	120.0
C8—C9—H9B	109.5	C35—C36—H36A	120.0
H9A—C9—H9B	109.5	C36—C37—C38	120.0 (4)
C8—C9—H9C	109.5	C36—C37—H37A	120.0
H9A—C9—H9C	109.5	C38—C37—H37A	120.0
H9B—C9—H9C	109.5	C37—C38—C39	120.0 (4)
C15—C10—C11	121.3 (3)	C37—C38—H38A	120.0
C15—C10—N4	120.0 (3)	C39—C38—H38A	120.0
C11—C10—N4	118.6 (3)	O4—C39—C38	129.4 (4)
C12—C11—C10	119.3 (4)	O4—C39—C34	110.6 (4)
C12—C11—H11	120.4	C38—C39—C34	120.0 (4)
C10—C11—H11	120.4	O5—C40—O6	121.4 (4)
C11—C12—C13	121.2 (3)	O5—C40—C41	121.0 (4)
C11—C12—H12	119.4	O6—C40—C41	117.6 (4)
C13—C12—H12	119.4	C46—C41—C42	119.3 (4)
C12—C13—C14	117.9 (3)	C46—C41—C40	120.4 (4)
C12—C13—C16	122.6 (3)	C42—C41—C40	120.3 (4)
C14—C13—C16	119.4 (4)	C43—C42—C41	120.9 (4)
C15—C14—C13	120.7 (4)	C43—C42—H42	119.6
C15—C14—H14	119.7	C41—C42—H42	119.6
C13—C14—H14	119.7	C44—C43—C42	119.3 (4)
C10—C15—C14	119.5 (4)	C44—C43—H43	120.3
C10—C15—H15	120.2	C42—C43—H43	120.3
C14—C15—H15	120.2	C43—C44—C45	122.3 (4)
C13—C16—H16A	109.5	C43—C44—H44	118.8
C13—C16—H16B	109.5	C45—C44—H44	118.8
H16A—C16—H16B	109.5	C44—C45—C46	118.2 (4)
C13—C16—H16C	109.5	C44—C45—H45	120.9
H16A—C16—H16C	109.5	C46—C45—H45	120.9
H16B—C16—H16C	109.5	O7—C46—C41	121.3 (4)
N5—C17—C18	122.0 (3)	O7—C46—C45	118.7 (4)
N5—C17—H17	119.0	C41—C46—C45	120.0 (4)
C18—C17—H17	119.0	N6—Cu1—N2	162.39 (12)
C17—C18—C19	119.0 (3)	N6—Cu1—N1	98.66 (12)
C17—C18—H18	120.5	N2—Cu1—N1	80.05 (12)
C19—C18—H18	120.5	N6—Cu1—N5	79.92 (12)
C18—C19—C20	120.0 (4)	N2—Cu1—N5	98.96 (12)
C18—C19—H19	120.0	N1—Cu1—N5	172.20 (12)
C20—C19—H19	120.0	N6—Cu1—O1	98.82 (12)
C19—C20—C21	117.4 (3)	N2—Cu1—O1	98.79 (12)
C19—C20—H20	121.3	N1—Cu1—O1	94.73 (12)
C21—C20—H20	121.3	N5—Cu1—O1	93.07 (12)
N5—C21—C20	122.9 (3)	C5—N1—C1	119.0 (3)
N5—C21—C22	112.0 (3)	C5—N1—Cu1	115.7 (2)
C20—C21—C22	125.1 (3)	C1—N1—Cu1	125.3 (2)
N6—C22—N8	108.9 (3)	C6—N2—N3	109.6 (3)
N6—C22—C21	117.7 (3)	C6—N2—Cu1	113.8 (2)
N8—C22—C21	133.3 (3)	N3—N2—Cu1	136.5 (2)
N7—C23—N8	110.0 (3)	C7—N3—N2	106.4 (3)
N7—C23—C24	123.6 (3)	C6—N4—C7	104.5 (3)
N8—C23—C24	126.2 (3)	C6—N4—C10	129.8 (3)
C23—C24—C25	109.5 (3)	C7—N4—C10	125.5 (3)
C23—C24—H24A	109.8	C21—N5—C17	118.6 (3)
C25—C24—H24A	109.8	C21—N5—Cu1	115.1 (2)
C23—C24—H24B	109.8	C17—N5—Cu1	126.2 (2)
C25—C24—H24B	109.8	C22—N6—N7	108.9 (3)
H24A—C24—H24B	108.2	C22—N6—Cu1	114.7 (2)
C24—C25—H25A	109.5	N7—N6—Cu1	135.6 (2)
C24—C25—H25B	109.5	C23—N7—N6	106.6 (3)
H25A—C25—H25B	109.5	C22—N8—C23	105.5 (3)
C24—C25—H25C	109.5	C22—N8—C26	129.2 (3)
H25A—C25—H25C	109.5	C23—N8—C26	125.1 (3)
H25B—C25—H25C	109.5	Cu1—O1—H1C	109.8
C27—C26—C31	121.6 (3)	Cu1—O1—H1A	109.3
C27—C26—N8	119.9 (3)	H1C—O1—H1A	109.8
C31—C26—N8	118.5 (3)	C39—O4—H4A	110.9
C26—C27—C28	118.7 (4)	C46—O7—H7	109.6
C26—C27—H27	120.7	H8A—O8—H8B	109.5
C28—C27—H27	120.7	H9F—O9—H9E	109.5
C27—C28—C29	120.9 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1C···O5	0.85	1.98	2.675 (4)	139
O1—H1A···O2	0.82	2.01	2.799 (4)	161
O4—H4A···O2	0.82	1.55	2.301 (4)	152
O7—H7···O6	0.82	1.73	2.470 (4)	148
O8—H8A···O5	0.85	2.00	2.808 (4)	157
O8—H8B···O3	0.85	2.29	2.753 (4)	114
O9—H9F···O8	0.85	2.13	2.976 (4)	180
O9—H9E···O8^i	0.85	2.33	3.015 (4)	139

Symmetry code: (i) −x+1, −y+1, −z+2.