(Perchlorato-κO)[3,6,14,21-tetra­aza-3,6-difur­yl-27,28-dihydroxy-10,25-dimeth­yltetra­cyclo­[18.4.3.3^8,12.0^15,20]octa­cosa-8,10,12(28),13,17,19,21,23,25,27(1)-deca­ene-κ⁴N,N′,O,O′]copper(II) perchlorate dimethyl­formamide solvate

In the title complex, [Cu(C₃₆H₃₆N₄O₄)(ClO₄)](ClO₄)·C₃H₇N, the coordination number of the Cu^II atom is 5 and the coordination configuration is best described as distorted tetra­gonal–pyramidal. There is a 13-membered macrocyclic ring in the mol­ecule. One perchlorate anion and the dimethyl­formamide mol­ecule do not participate in coordination. There are four intra­molecular hydrogen bonds in the structure and these constrain the conformation of the macrocycle and enhance its stability.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.061
• wR factor = 0.140
• Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); 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.

[3,6,14,21-Tetraaza-3,6-difuryl-10,25-dimethyl-27,28- dioxotetracyclo[18.4.3.3^8,12.0^15,20]octacosa- 8,10,12 (28),13,17,19,21,23,25,27 (1)-decaene-κ⁴N,N',O,O'](perchlorato- κO)copper(II) perchlorate dimethylformamide solvate

Crystal data

[Cu(C36H36N4O4)(ClO4)](ClO4)·C3H7N	F(000) = 1916
Mr = 924.22	Dx = 1.524 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1784 reflections
a = 9.717 (2) Å	θ = 2.0–25.5°
b = 27.863 (3) Å	µ = 0.75 mm^−1
c = 14.902 (5) Å	T = 293 K
β = 93.06 (2)°	Prism, yellow
V = 4028.9 (16) Å^3	0.32 × 0.26 × 0.24 mm
Z = 4

Data collection

Bruker SMART Apex CCD area-detector diffractometer	7914 independent reflections
Radiation source: sealed tube	6113 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
φ and ω scans	θmax = 26.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −11→11
Tmin = 0.79, Tmax = 0.84	k = −16→34
17136 measured reflections	l = −14→18

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.140	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0743P)^2 + 0.9397P] where P = (Fo^2 + 2Fc^2)/3
7914 reflections	(Δ/σ)max < 0.001
543 parameters	Δρmax = 0.33 e Å^−3
0 restraints	Δρmin = −0.75 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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 6.5772 (0.0074) x + 2.3014 (0.0251) y + 11.4232 (0.0100) z = 6.3059 (0.0252)

* -0.0459 (0.0011) Cu1 * 0.0308 (0.0013) O1 * -0.0071 (0.0013) O2 * -0.0075 (0.0013) N1 * 0.0298 (0.0013) N2

Rms deviation of fitted atoms = 0.0285

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

	x	y	z	Uiso*/Ueq
C1	−0.2009 (3)	0.93373 (13)	−0.0449 (2)	0.0252 (7)
H1	−0.2721	0.9426	−0.0857	0.030*
C2	−0.0599 (3)	0.94964 (13)	−0.0459 (2)	0.0265 (7)
H2	−0.0236	0.9705	−0.0872	0.032*
C3	0.0129 (3)	0.92754 (12)	0.0278 (2)	0.0221 (7)
H3	0.1061	0.9310	0.0441	0.026*
C4	−0.0809 (3)	0.89987 (13)	0.0708 (2)	0.0262 (7)
C5	−0.0688 (4)	0.86921 (13)	0.1487 (2)	0.0280 (8)
H5C	0.0226	0.8552	0.1494	0.034*
H5D	−0.1346	0.8431	0.1416	0.034*
C6	−0.0705 (3)	0.85641 (13)	0.3122 (2)	0.0271 (8)
H6A	−0.1499	0.8355	0.3039	0.033*
H6B	−0.0807	0.8736	0.3681	0.033*
C7	0.0605 (3)	0.82299 (14)	0.3266 (3)	0.0305 (8)
H7A	0.0370	0.7931	0.3554	0.037*
H7B	0.0880	0.8151	0.2667	0.037*
C8	0.3134 (4)	0.82592 (14)	0.3435 (3)	0.0319 (8)
H8A	0.3203	0.8326	0.2800	0.038*
H8B	0.3900	0.8418	0.3756	0.038*
C9	0.3259 (4)	0.77561 (14)	0.3573 (2)	0.0294 (8)
C10	0.2920 (4)	0.73485 (14)	0.3015 (3)	0.0309 (8)
H10	0.2513	0.7357	0.2436	0.037*
C11	0.3319 (3)	0.69274 (12)	0.3508 (2)	0.0236 (7)
H11	0.3208	0.6612	0.3312	0.028*
C12	0.3916 (3)	0.70776 (12)	0.4351 (2)	0.0226 (7)
H12	0.4273	0.6876	0.4804	0.027*
C13	0.1660 (3)	0.84519 (13)	0.4718 (2)	0.0258 (7)
H13A	0.0711	0.8525	0.4836	0.031*
H13B	0.1849	0.8127	0.4926	0.031*
C14	0.2562 (4)	0.87831 (14)	0.5239 (2)	0.0292 (8)
C15	0.3530 (3)	0.86246 (13)	0.5908 (2)	0.0246 (7)
H15	0.3612	0.8298	0.6032	0.030*
C16	0.4361 (3)	0.89495 (13)	0.6385 (2)	0.0257 (7)
C17	0.4235 (3)	0.94392 (12)	0.6198 (2)	0.0248 (7)
H17	0.4794	0.9658	0.6517	0.030*
C18	0.3288 (3)	0.95994 (13)	0.5545 (2)	0.0265 (8)
C19	0.2454 (3)	0.92719 (13)	0.5073 (2)	0.0261 (7)
C20	0.5378 (4)	0.87720 (15)	0.7135 (3)	0.0335 (9)
H20A	0.6293	0.8874	0.7012	0.050*
H20B	0.5348	0.8428	0.7163	0.050*
H20C	0.5129	0.8903	0.7700	0.050*
C21	0.3242 (4)	1.01129 (14)	0.5421 (3)	0.0323 (8)
H21	0.3858	1.0294	0.5779	0.039*
C22	0.2456 (4)	1.08476 (14)	0.4744 (2)	0.0286 (8)
C23	0.3324 (4)	1.11602 (15)	0.5223 (3)	0.0325 (8)
H23	0.3997	1.1040	0.5630	0.039*
C24	0.3194 (4)	1.16523 (15)	0.5098 (3)	0.0311 (8)
H24	0.3779	1.1861	0.5421	0.037*
C25	0.2188 (4)	1.18335 (14)	0.4488 (2)	0.0296 (8)
H25	0.2106	1.2163	0.4397	0.035*
C26	0.1343 (4)	1.15296 (13)	0.4036 (2)	0.0280 (8)
H26	0.0665	1.1648	0.3631	0.034*
C27	0.1446 (4)	1.10234 (13)	0.4146 (2)	0.0255 (7)
C28	−0.0385 (4)	1.07764 (13)	0.3044 (2)	0.0283 (8)
H28	−0.0490	1.1102	0.2922	0.034*
C29	−0.1226 (4)	1.04769 (13)	0.2560 (2)	0.0295 (8)
C30	−0.2101 (4)	1.06826 (15)	0.1891 (2)	0.0322 (8)
H30	−0.2076	1.1012	0.1789	0.039*
C31	−0.3017 (4)	1.03928 (13)	0.1372 (2)	0.0286 (8)
C32	−0.3019 (4)	0.99021 (14)	0.1513 (3)	0.0306 (8)
H32	−0.3600	0.9707	0.1156	0.037*
C33	−0.2157 (3)	0.96983 (13)	0.2184 (2)	0.0249 (7)
C34	−0.1260 (4)	0.99819 (13)	0.2688 (2)	0.0269 (7)
C35	−0.2213 (4)	0.91738 (13)	0.2429 (2)	0.0276 (8)
H35A	−0.2870	0.9013	0.2017	0.033*
H35B	−0.2541	0.9143	0.3029	0.033*
C36	−0.3933 (4)	1.05836 (14)	0.0639 (2)	0.0325 (8)
H36A	−0.4809	1.0661	0.0870	0.049*
H36B	−0.4058	1.0347	0.0174	0.049*
H36C	−0.3533	1.0867	0.0397	0.049*
C37	0.4832 (4)	0.84587 (15)	0.0831 (3)	0.0375 (9)
H37A	0.4966	0.8742	0.0479	0.056*
H37B	0.5712	0.8327	0.1024	0.056*
H37C	0.4330	0.8540	0.1347	0.056*
C38	0.4688 (4)	0.78517 (16)	−0.0397 (3)	0.0399 (10)
H38A	0.4724	0.8026	−0.0951	0.060*
H38B	0.4188	0.7558	−0.0501	0.060*
H38C	0.5608	0.7780	−0.0169	0.060*
C39	0.2577 (4)	0.80581 (13)	0.0385 (2)	0.0276 (8)
H39	0.2093	0.7942	−0.0125	0.033*
Cl1	0.31789 (9)	0.95423 (3)	0.24048 (6)	0.02622 (19)
Cl2	0.70596 (8)	0.74491 (3)	0.22272 (5)	0.02455 (19)
Cu1	0.10210 (4)	1.003902 (14)	0.40453 (3)	0.02437 (13)
N1	0.0573 (3)	1.06757 (11)	0.36926 (19)	0.0261 (6)
N2	0.2435 (3)	1.03449 (12)	0.4864 (2)	0.0338 (7)
N3	−0.0804 (3)	0.89212 (11)	0.2396 (2)	0.0303 (7)
N4	0.1815 (3)	0.84695 (11)	0.3735 (2)	0.0279 (7)
N5	0.4004 (3)	0.81387 (11)	0.0250 (2)	0.0289 (7)
O1	−0.0440 (2)	0.97528 (9)	0.33290 (15)	0.0233 (5)
H1A	−0.0033	0.9484	0.3027	0.028*
O2	0.1470 (2)	0.93968 (9)	0.44671 (15)	0.0242 (5)
H2B	0.1647	0.9213	0.3932	0.029*
O3	−0.2124 (2)	0.90239 (9)	0.02836 (16)	0.0248 (5)
O4	0.3879 (2)	0.75839 (8)	0.43880 (16)	0.0272 (5)
O5	0.2721 (2)	1.00169 (9)	0.26882 (17)	0.0289 (6)
O6	0.3663 (3)	0.96044 (10)	0.15609 (17)	0.0335 (6)
O7	0.2016 (2)	0.92078 (9)	0.23772 (17)	0.0286 (5)
O8	0.4193 (2)	0.93619 (8)	0.30244 (16)	0.0259 (5)
O9	0.6513 (3)	0.78369 (11)	0.2674 (2)	0.0420 (7)
O10	0.8474 (2)	0.74792 (10)	0.22660 (17)	0.0319 (6)
O11	0.6653 (3)	0.70062 (11)	0.24467 (18)	0.0365 (6)
O12	0.6573 (3)	0.74450 (10)	0.13739 (18)	0.0358 (6)
O13	0.1864 (3)	0.81083 (10)	0.10146 (18)	0.0370 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0225 (15)	0.0254 (18)	0.0285 (19)	0.0038 (14)	0.0081 (13)	0.0000 (15)
C2	0.0240 (16)	0.0262 (19)	0.0306 (19)	0.0048 (14)	0.0119 (14)	−0.0029 (15)
C3	0.0261 (15)	0.0195 (17)	0.0221 (16)	0.0016 (13)	0.0140 (13)	0.0009 (13)
C4	0.0256 (16)	0.0244 (18)	0.0296 (18)	0.0028 (14)	0.0090 (14)	0.0014 (15)
C5	0.0265 (16)	0.028 (2)	0.0307 (19)	−0.0052 (15)	0.0084 (14)	−0.0018 (15)
C6	0.0257 (16)	0.0249 (18)	0.0318 (19)	−0.0025 (14)	0.0115 (14)	−0.0031 (15)
C7	0.0270 (17)	0.034 (2)	0.032 (2)	−0.0023 (15)	0.0121 (15)	−0.0094 (17)
C8	0.0344 (18)	0.028 (2)	0.035 (2)	0.0063 (16)	0.0140 (16)	−0.0026 (16)
C9	0.0377 (18)	0.0203 (18)	0.0307 (19)	0.0021 (15)	0.0078 (15)	0.0018 (15)
C10	0.0349 (18)	0.028 (2)	0.0292 (19)	−0.0034 (15)	−0.0058 (15)	−0.0010 (16)
C11	0.0322 (17)	0.0171 (17)	0.0219 (17)	0.0002 (14)	0.0044 (13)	0.0017 (13)
C12	0.0281 (16)	0.0177 (16)	0.0230 (17)	−0.0034 (13)	0.0103 (13)	0.0010 (14)
C13	0.0284 (16)	0.0231 (18)	0.0266 (19)	0.0009 (14)	0.0077 (14)	−0.0004 (14)
C14	0.0279 (17)	0.030 (2)	0.0290 (19)	−0.0021 (15)	−0.0057 (14)	0.0006 (15)
C15	0.0261 (16)	0.0208 (17)	0.0268 (18)	0.0007 (13)	0.0007 (13)	0.0008 (14)
C16	0.0260 (16)	0.0230 (18)	0.0274 (18)	0.0046 (14)	−0.0066 (14)	0.0057 (15)
C17	0.0301 (16)	0.0209 (17)	0.0239 (17)	0.0040 (14)	0.0060 (13)	0.0007 (14)
C18	0.0264 (16)	0.0246 (19)	0.0295 (19)	0.0041 (14)	0.0102 (14)	0.0012 (15)
C19	0.0277 (16)	0.0262 (19)	0.0246 (18)	0.0081 (14)	0.0050 (13)	0.0007 (15)
C20	0.0359 (18)	0.035 (2)	0.0287 (19)	0.0185 (17)	−0.0065 (15)	0.0096 (17)
C21	0.0392 (19)	0.026 (2)	0.033 (2)	0.0012 (16)	0.0044 (16)	−0.0006 (16)
C22	0.0326 (18)	0.0263 (19)	0.0281 (19)	−0.0029 (15)	0.0130 (15)	0.0010 (15)
C23	0.0311 (18)	0.035 (2)	0.032 (2)	−0.0048 (16)	0.0069 (15)	−0.0014 (17)
C24	0.0263 (16)	0.035 (2)	0.031 (2)	−0.0034 (15)	−0.0044 (15)	−0.0052 (17)
C25	0.0309 (17)	0.0250 (19)	0.034 (2)	0.0000 (15)	0.0097 (15)	−0.0016 (16)
C26	0.0324 (17)	0.0243 (18)	0.0282 (19)	0.0044 (15)	0.0090 (14)	−0.0013 (15)
C27	0.0309 (16)	0.0193 (17)	0.0270 (18)	−0.0012 (14)	0.0069 (14)	0.0026 (14)
C28	0.0332 (18)	0.0251 (19)	0.0278 (19)	0.0059 (15)	0.0131 (15)	0.0031 (15)
C29	0.043 (2)	0.0207 (17)	0.0254 (18)	0.0017 (16)	0.0089 (15)	0.0019 (15)
C30	0.042 (2)	0.0260 (19)	0.0289 (19)	−0.0001 (16)	0.0066 (16)	0.0016 (16)
C31	0.0304 (17)	0.0219 (18)	0.033 (2)	0.0075 (15)	0.0003 (15)	0.0002 (15)
C32	0.0312 (17)	0.027 (2)	0.033 (2)	−0.0012 (15)	−0.0074 (15)	0.0010 (15)
C33	0.0256 (16)	0.0203 (17)	0.0295 (18)	0.0031 (14)	0.0085 (13)	0.0028 (15)
C34	0.0301 (16)	0.0239 (18)	0.0274 (18)	0.0028 (15)	0.0079 (14)	−0.0010 (15)
C35	0.0316 (17)	0.0231 (18)	0.0287 (19)	−0.0055 (15)	0.0080 (15)	−0.0001 (15)
C36	0.0334 (18)	0.033 (2)	0.030 (2)	0.0151 (17)	−0.0082 (15)	0.0045 (17)
C37	0.040 (2)	0.033 (2)	0.042 (2)	−0.0074 (17)	0.0188 (17)	−0.0075 (18)
C38	0.039 (2)	0.040 (2)	0.041 (2)	−0.0039 (18)	0.0125 (18)	−0.0038 (19)
C39	0.0326 (17)	0.0213 (18)	0.0298 (19)	0.0002 (15)	0.0109 (15)	0.0010 (15)
Cl1	0.0331 (4)	0.0150 (4)	0.0313 (4)	−0.0001 (3)	0.0087 (3)	0.0013 (3)
Cl2	0.0320 (4)	0.0167 (4)	0.0258 (4)	0.0003 (3)	0.0087 (3)	0.0001 (3)
Cu1	0.0325 (2)	0.0163 (2)	0.0251 (2)	0.00019 (17)	0.00895 (17)	−0.00022 (17)
N1	0.0342 (15)	0.0205 (14)	0.0250 (15)	0.0017 (13)	0.0147 (12)	0.0004 (13)
N2	0.0283 (15)	0.0354 (19)	0.0371 (18)	−0.0023 (14)	−0.0032 (13)	−0.0010 (15)
N3	0.0343 (15)	0.0253 (16)	0.0321 (17)	−0.0029 (13)	0.0089 (13)	−0.0030 (13)
N4	0.0258 (14)	0.0278 (16)	0.0313 (17)	0.0010 (12)	0.0111 (12)	−0.0009 (13)
N5	0.0286 (14)	0.0281 (17)	0.0310 (16)	−0.0049 (13)	0.0123 (12)	−0.0086 (14)
O1	0.0265 (11)	0.0221 (12)	0.0226 (12)	0.0020 (10)	0.0132 (9)	0.0047 (10)
O2	0.0226 (11)	0.0269 (13)	0.0232 (12)	0.0058 (10)	0.0022 (9)	−0.0003 (10)
O3	0.0241 (11)	0.0238 (13)	0.0269 (13)	−0.0006 (10)	0.0064 (9)	−0.0020 (10)
O4	0.0324 (12)	0.0189 (12)	0.0318 (13)	−0.0020 (10)	0.0148 (10)	0.0003 (10)
O5	0.0323 (12)	0.0231 (13)	0.0330 (14)	−0.0048 (10)	0.0166 (10)	−0.0098 (11)
O6	0.0362 (13)	0.0329 (15)	0.0325 (14)	−0.0047 (12)	0.0119 (11)	−0.0025 (12)
O7	0.0349 (13)	0.0216 (13)	0.0303 (14)	−0.0027 (10)	0.0114 (10)	0.0036 (10)
O8	0.0340 (12)	0.0162 (12)	0.0281 (13)	0.0040 (10)	0.0069 (10)	0.0021 (10)
O9	0.0335 (14)	0.0434 (17)	0.0501 (18)	−0.0146 (13)	0.0101 (12)	−0.0101 (14)
O10	0.0289 (12)	0.0329 (14)	0.0350 (14)	−0.0019 (11)	0.0135 (10)	−0.0048 (12)
O11	0.0302 (13)	0.0414 (17)	0.0383 (16)	−0.0032 (12)	0.0055 (11)	0.0017 (13)
O12	0.0306 (13)	0.0405 (17)	0.0369 (15)	−0.0012 (12)	0.0059 (11)	−0.0014 (13)
O13	0.0490 (15)	0.0307 (15)	0.0327 (15)	0.0034 (12)	0.0154 (12)	0.0029 (12)

Geometric parameters (Å, º)

C1—O3	1.407 (4)	C23—H23	0.9300
C1—C2	1.441 (5)	C24—C25	1.393 (5)
C1—H1	0.9300	C24—H24	0.9300
C2—C3	1.415 (5)	C25—C26	1.337 (5)
C2—H2	0.9300	C25—H25	0.9300
C3—C4	1.377 (5)	C26—C27	1.423 (5)
C3—H3	0.9300	C26—H26	0.9300
C4—O3	1.396 (4)	C27—N1	1.433 (5)
C4—C5	1.441 (5)	C28—N1	1.335 (5)
C5—N3	1.507 (4)	C28—C29	1.350 (5)
C5—H5C	0.9700	C28—H28	0.9300
C5—H5D	0.9700	C29—C34	1.393 (5)
C6—N3	1.470 (5)	C29—C30	1.398 (5)
C6—C7	1.583 (5)	C30—C31	1.403 (5)
C6—H6A	0.9700	C30—H30	0.9300
C6—H6B	0.9700	C31—C32	1.383 (5)
C7—N4	1.493 (5)	C31—C36	1.471 (5)
C7—H7A	0.9700	C32—C33	1.392 (5)
C7—H7B	0.9700	C32—H32	0.9300
C8—C9	1.421 (5)	C33—C34	1.370 (5)
C8—N4	1.499 (4)	C33—C35	1.508 (5)
C8—H8A	0.9700	C34—O1	1.369 (4)
C8—H8B	0.9700	C35—N3	1.542 (5)
C9—O4	1.410 (4)	C35—H35A	0.9700
C9—C10	1.436 (5)	C35—H35B	0.9700
C10—C11	1.427 (5)	C36—H36A	0.9600
C10—H10	0.9300	C36—H36B	0.9600
C11—C12	1.419 (5)	C36—H36C	0.9600
C11—H11	0.9300	C37—N5	1.456 (5)
C12—O4	1.412 (4)	C37—H37A	0.9600
C12—H12	0.9300	C37—H37B	0.9600
C13—C14	1.466 (5)	C37—H37C	0.9600
C13—N4	1.482 (4)	C38—N5	1.441 (5)
C13—H13A	0.9700	C38—H38A	0.9600
C13—H13B	0.9700	C38—H38B	0.9600
C14—C19	1.387 (5)	C38—H38C	0.9600
C14—C15	1.405 (5)	C39—O13	1.204 (4)
C15—C16	1.384 (5)	C39—N5	1.430 (4)
C15—H15	0.9300	C39—H39	0.9300
C16—C17	1.397 (5)	Cl1—O6	1.377 (3)
C16—C20	1.534 (4)	Cl1—O8	1.407 (3)
C17—C18	1.377 (5)	Cl1—O7	1.464 (3)
C17—H17	0.9300	Cl1—O5	1.465 (2)
C18—C19	1.387 (5)	Cl2—O12	1.333 (3)
C18—C21	1.443 (5)	Cl2—O11	1.342 (3)
C19—O2	1.327 (4)	Cl2—O10	1.375 (3)
C20—H20A	0.9600	Cl2—O9	1.389 (3)
C20—H20B	0.9600	Cu1—N1	1.894 (3)
C20—H20C	0.9600	Cu1—O1	1.905 (2)
C21—N2	1.285 (5)	Cu1—O2	1.938 (2)
C21—H21	0.9300	Cu1—N2	1.981 (3)
C22—C27	1.380 (5)	Cu1—O5	2.679 (2)
C22—C23	1.384 (5)	O1—H1A	0.9700
C22—N2	1.412 (5)	O2—H2B	0.9700
C23—C24	1.389 (5)
O3—C1—C2	108.3 (3)	C25—C26—H26	119.8
O3—C1—H1	125.9	C27—C26—H26	118.0
C2—C1—H1	125.9	C22—C27—C26	118.0 (3)
C3—C2—C1	107.1 (3)	C22—C27—N1	116.6 (3)
C3—C2—H2	126.4	C26—C27—N1	125.4 (3)
C1—C2—H2	126.4	N1—C28—C29	129.5 (4)
C4—C3—C2	106.8 (3)	N1—C28—H28	114.3
C4—C3—H3	126.6	C29—C28—H28	116.2
C2—C3—H3	126.6	C28—C29—C34	123.8 (4)
C3—C4—O3	111.9 (3)	C28—C29—C30	117.1 (3)
C3—C4—C5	132.7 (3)	C34—C29—C30	119.0 (4)
O3—C4—C5	115.3 (3)	C29—C30—C31	120.1 (4)
C4—C5—N3	117.8 (3)	C29—C30—H30	120.0
C4—C5—H5C	106.5	C31—C30—H30	120.0
N3—C5—H5C	105.8	C32—C31—C30	119.4 (3)
C4—C5—H5D	109.4	C32—C31—C36	117.6 (3)
N3—C5—H5D	109.5	C30—C31—C36	122.8 (3)
H5C—C5—H5D	107.3	C31—C32—C33	120.4 (3)
N3—C6—C7	121.2 (3)	C31—C32—H32	119.8
N3—C6—H6A	107.0	C33—C32—H32	119.8
C7—C6—H6A	107.0	C34—C33—C32	120.0 (3)
N3—C6—H6B	107.0	C34—C33—C35	117.2 (3)
C7—C6—H6B	107.0	C32—C33—C35	122.8 (3)
H6A—C6—H6B	106.8	O1—C34—C33	116.3 (3)
N4—C7—C6	114.1 (3)	O1—C34—C29	122.7 (3)
N4—C7—H7A	112.1	C33—C34—C29	121.0 (3)
C6—C7—H7A	111.0	C33—C35—N3	113.0 (3)
N4—C7—H7B	106.4	C33—C35—H35A	109.0
C6—C7—H7B	105.5	N3—C35—H35A	109.0
H7A—C7—H7B	107.3	C33—C35—H35B	109.0
C9—C8—N4	114.2 (3)	N3—C35—H35B	109.0
C9—C8—H8A	108.7	H35A—C35—H35B	107.8
N4—C8—H8A	108.7	C31—C36—H36A	109.1
C9—C8—H8B	108.7	C31—C36—H36B	109.6
N4—C8—H8B	108.7	H36A—C36—H36B	109.5
H8A—C8—H8B	107.6	C31—C36—H36C	109.6
O4—C9—C8	119.3 (3)	H36A—C36—H36C	109.5
O4—C9—C10	107.7 (3)	H36B—C36—H36C	109.5
C8—C9—C10	132.9 (4)	N5—C37—H37A	105.3
C11—C10—C9	107.7 (3)	N5—C37—H37B	113.5
C11—C10—H10	126.1	H37A—C37—H37B	109.5
C9—C10—H10	126.1	N5—C37—H37C	109.4
C12—C11—C10	107.5 (3)	H37A—C37—H37C	109.5
C12—C11—H11	126.3	H37B—C37—H37C	109.5
C10—C11—H11	126.3	N5—C38—H38A	109.5
O4—C12—C11	108.6 (3)	N5—C38—H38B	109.5
O4—C12—H12	125.7	H38A—C38—H38B	109.5
C11—C12—H12	125.7	N5—C38—H38C	109.5
C14—C13—N4	114.4 (3)	H38A—C38—H38C	109.5
C14—C13—H13A	108.7	H38B—C38—H38C	109.5
N4—C13—H13A	108.7	O13—C39—N5	134.0 (4)
C14—C13—H13B	108.7	O13—C39—H39	113.0
N4—C13—H13B	108.7	N5—C39—H39	113.0
H13A—C13—H13B	107.6	O6—Cl1—O8	112.53 (16)
C19—C14—C15	118.4 (3)	O6—Cl1—O7	110.80 (16)
C19—C14—C13	119.1 (3)	O8—Cl1—O7	107.67 (15)
C15—C14—C13	122.4 (3)	O6—Cl1—O5	105.88 (16)
C16—C15—C14	120.6 (3)	O8—Cl1—O5	110.25 (15)
C16—C15—H15	119.7	O7—Cl1—O5	109.70 (14)
C14—C15—H15	119.7	O12—Cl2—O11	97.51 (18)
C15—C16—C17	119.6 (3)	O12—Cl2—O10	110.09 (16)
C15—C16—C20	119.9 (3)	O11—Cl2—O10	110.63 (17)
C17—C16—C20	120.4 (3)	O12—Cl2—O9	109.78 (18)
C18—C17—C16	120.3 (3)	O11—Cl2—O9	118.27 (17)
C18—C17—H17	119.8	O10—Cl2—O9	109.83 (16)
C16—C17—H17	119.8	N1—Cu1—O1	94.77 (12)
C17—C18—C19	119.7 (3)	N1—Cu1—O2	177.19 (11)
C17—C18—C21	115.3 (3)	O1—Cu1—O2	86.75 (10)
C19—C18—C21	125.0 (3)	N1—Cu1—N2	84.82 (14)
O2—C19—C18	123.6 (3)	O1—Cu1—N2	175.49 (12)
O2—C19—C14	115.1 (3)	O2—Cu1—N2	93.49 (12)
C18—C19—C14	121.3 (3)	C28—N1—C27	124.9 (3)
C16—C20—H20A	109.5	C28—N1—Cu1	122.6 (3)
C16—C20—H20B	109.5	C27—N1—Cu1	112.4 (2)
H20A—C20—H20B	109.5	C21—N2—C22	124.6 (3)
C16—C20—H20C	109.5	C21—N2—Cu1	124.1 (3)
H20A—C20—H20C	109.5	C22—N2—Cu1	111.3 (2)
H20B—C20—H20C	109.5	C6—N3—C5	111.7 (3)
N2—C21—C18	126.6 (4)	C6—N3—C35	108.0 (3)
N2—C21—H21	116.7	C5—N3—C35	109.3 (3)
C18—C21—H21	116.7	C13—N4—C7	109.2 (3)
C27—C22—C23	120.2 (4)	C13—N4—C8	114.5 (3)
C27—C22—N2	114.8 (3)	C7—N4—C8	110.5 (3)
C23—C22—N2	124.9 (3)	C39—N5—C38	119.5 (3)
C22—C23—C24	120.2 (4)	C39—N5—C37	121.5 (3)
C22—C23—H23	119.9	C38—N5—C37	118.5 (3)
C24—C23—H23	119.9	C34—O1—Cu1	125.8 (2)
C23—C24—C25	120.1 (3)	C34—O1—H1A	105.9
C23—C24—H24	119.9	Cu1—O1—H1A	105.9
C25—C24—H24	119.9	C19—O2—Cu1	127.2 (2)
C26—C25—C24	119.3 (4)	C19—O2—H2B	105.5
C26—C25—H25	120.3	Cu1—O2—H2B	105.5
C24—C25—H25	120.3	C4—O3—C1	105.9 (2)
C25—C26—C27	122.1 (4)	C9—O4—C12	108.5 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N3	0.97	1.96	2.716 (4)	133
O1—H1A···O7	0.97	2.39	3.221 (3)	144
O2—H2B···N4	0.97	2.10	2.832 (4)	131
O2—H2B···O7	0.97	2.36	3.230 (3)	148