Bis(1,10-phenanthroline-κN,N')(phenyl-acetato-κO)copper(II) phenyl-acetate hexa-hydrate.

In the title compound, [Cu(C(8)H(7)O(2))(C(12)H(8)N(2))(2)](C(8)H(7)O(2))·6H(2)O, the Cu atom is in a distorted square-pyramidal coordination environment. The six crystallographically independent uncoordinated water mol-ecules are inter-connected by hydrogen bonds, completing dodeca-water (H(2)O)(12) clusters which are hydrogen bonded to the carboxyl-ate groups of phenyl-acetate anions, building up one-dimensional anionic chains propagating along [100]. Between the cationic and anionic chains are hydrogen bonds from water mol-ecules to the carboxyl-ate O atoms belonging to the phenyl-acetato ligands.

Related literature

For general background, see: Kuroda-Sowa et al. (1997 ▶); Lehn (2007 ▶); Li et al. (2008 ▶). For related structures, see: Addison & Rao (1984 ▶); Baruah et al. (2007 ▶); Liu & Xu (2005 ▶); Ma et al. (2005 ▶); Sugimori et al. (1997 ▶); Zheng et al. (2001 ▶).

Experimental

Crystal data

[Cu(C8H7O2)(C12H8N2)2](C8H7O2)·6H2O

M = 802.33

Triclinic,

a = 11.499 (2) Å

b = 11.903 (2) Å

c = 16.066 (3) Å

α = 71.00 (3)°

β = 72.97 (3)°

γ = 68.93 (3)°

V = 1901.3 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.64 mm−1

T = 293 (2) K

0.37 × 0.35 × 0.17 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.793, T max = 0.902

18689 measured reflections

8680 independent reflections

7070 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.095

S = 1.08

8680 reflections

496 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.39 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808032480/pk2118sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808032480/pk2118Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Cu(C8H7O2)(C12H8N2)2](C8H7O2)·6H2O	Z = 2
Mr = 802.33	F(000) = 838
Triclinic, P1	Dx = 1.401 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.499 (2) Å	Cell parameters from 14647 reflections
b = 11.903 (2) Å	θ = 3.0–27.5°
c = 16.066 (3) Å	µ = 0.64 mm−1
α = 71.00 (3)°	T = 293 K
β = 72.97 (3)°	Prism, blue
γ = 68.93 (3)°	0.37 × 0.35 × 0.17 mm
V = 1901.3 (8) Å3

Rigaku R-AXIS RAPID diffractometer	8680 independent reflections
Radiation source: fine-focus sealed tube	7070 reflections with I > 2σ(I)
graphite	Rint = 0.030
ω scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −14→14
Tmin = 0.793, Tmax = 0.902	k = −15→15
18689 measured reflections	l = −20→20

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0351P)2 + 1.3044P] where P = (Fo2 + 2Fc2)/3
8680 reflections	(Δ/σ)max = 0.002
496 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.39 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

	x	y	z	Uiso*/Ueq
Cu	0.68956 (2)	0.48613 (2)	0.746890 (15)	0.01698 (7)
N1	0.88512 (16)	0.37869 (15)	0.70294 (11)	0.0202 (3)
N2	0.75896 (16)	0.62363 (15)	0.66308 (10)	0.0187 (3)
C1	0.9447 (2)	0.25741 (19)	0.72006 (14)	0.0246 (4)
H1A	0.8995	0.2027	0.7579	0.030*
C2	1.0735 (2)	0.2091 (2)	0.68296 (15)	0.0299 (5)
H2A	1.1123	0.1238	0.6966	0.036*
C3	1.1417 (2)	0.2876 (2)	0.62679 (14)	0.0282 (5)
H3A	1.2272	0.2565	0.6024	0.034*
C4	1.08088 (19)	0.4164 (2)	0.60633 (13)	0.0234 (4)
C5	1.1439 (2)	0.5061 (2)	0.54605 (13)	0.0263 (5)
H5A	1.2291	0.4792	0.5192	0.032*
C6	1.0814 (2)	0.6284 (2)	0.52797 (13)	0.0274 (5)
H6A	1.1245	0.6846	0.4893	0.033*
C7	0.9498 (2)	0.6735 (2)	0.56728 (12)	0.0223 (4)
C8	0.8792 (2)	0.7998 (2)	0.54857 (13)	0.0265 (5)
H8A	0.9184	0.8592	0.5104	0.032*
C9	0.7529 (2)	0.8349 (2)	0.58661 (14)	0.0265 (5)
H9A	0.7059	0.9183	0.5749	0.032*
C10	0.6947 (2)	0.74424 (19)	0.64352 (13)	0.0228 (4)
H10A	0.6084	0.7689	0.6685	0.027*
C11	0.88530 (19)	0.58773 (19)	0.62585 (12)	0.0190 (4)
C12	0.95214 (19)	0.45701 (19)	0.64659 (12)	0.0192 (4)
N3	0.71006 (15)	0.52113 (15)	0.85842 (10)	0.0184 (3)
N4	0.61981 (15)	0.35480 (15)	0.84204 (10)	0.0179 (3)
C13	0.75535 (19)	0.60510 (19)	0.86524 (14)	0.0234 (4)
H13A	0.7805	0.6612	0.8131	0.028*
C14	0.7671 (2)	0.6132 (2)	0.94739 (15)	0.0276 (5)
H14A	0.8004	0.6728	0.9491	0.033*
C15	0.7289 (2)	0.5323 (2)	1.02531 (14)	0.0267 (5)
H15A	0.7355	0.5369	1.0804	0.032*
C16	0.67958 (19)	0.44215 (19)	1.02106 (13)	0.0215 (4)
C17	0.6358 (2)	0.3548 (2)	1.09815 (13)	0.0255 (4)
H17A	0.6405	0.3554	1.1548	0.031*
C18	0.5875 (2)	0.2709 (2)	1.09022 (13)	0.0253 (4)
H18A	0.5588	0.2156	1.1415	0.030*
C19	0.57996 (18)	0.26646 (18)	1.00364 (13)	0.0204 (4)
C20	0.53024 (19)	0.18274 (18)	0.99020 (13)	0.0236 (4)
H20A	0.4996	0.1256	1.0390	0.028*
C21	0.5275 (2)	0.18630 (19)	0.90460 (14)	0.0241 (4)
H21A	0.4949	0.1316	0.8949	0.029*
C22	0.57429 (19)	0.27314 (18)	0.83178 (13)	0.0219 (4)
H22A	0.5734	0.2736	0.7740	0.026*
C23	0.62315 (17)	0.35128 (17)	0.92720 (12)	0.0169 (4)
C24	0.67262 (18)	0.44035 (18)	0.93590 (12)	0.0180 (4)
O1	0.60569 (13)	0.47269 (12)	0.65901 (9)	0.0194 (3)
O2	0.46263 (13)	0.63541 (13)	0.70364 (9)	0.0227 (3)
C25	0.49547 (18)	0.55256 (18)	0.66273 (12)	0.0178 (4)
C26	0.40023 (19)	0.53846 (19)	0.62087 (12)	0.0196 (4)
H26A	0.3618	0.6176	0.5828	0.024*
H26B	0.4432	0.4792	0.5841	0.024*
C27	0.29830 (18)	0.49355 (18)	0.69518 (12)	0.0184 (4)
C28	0.19012 (19)	0.57800 (19)	0.72970 (13)	0.0223 (4)
H28A	0.1794	0.6628	0.7065	0.027*
C29	0.0977 (2)	0.5369 (2)	0.79870 (14)	0.0267 (4)
H29A	0.0255	0.5944	0.8212	0.032*
C30	0.1120 (2)	0.4103 (2)	0.83452 (14)	0.0271 (5)
H30A	0.0501	0.3828	0.8808	0.033*
C31	0.2201 (2)	0.3260 (2)	0.79992 (14)	0.0269 (5)
H31A	0.2306	0.2412	0.8232	0.032*
C32	0.3130 (2)	0.36672 (19)	0.73082 (13)	0.0226 (4)
H32A	0.3851	0.3092	0.7083	0.027*
O3	0.92255 (14)	0.04315 (14)	0.61308 (10)	0.0298 (3)
O4	0.74454 (15)	0.07607 (14)	0.71534 (10)	0.0311 (4)
C33	0.8540 (2)	0.01148 (18)	0.68752 (14)	0.0239 (4)
C34	0.9041 (3)	−0.1168 (2)	0.74904 (15)	0.0358 (6)
H34A	0.8474	−0.1657	0.7587	0.043*
H34B	0.9869	−0.1587	0.7186	0.043*
C35	0.9159 (2)	−0.11314 (18)	0.83942 (15)	0.0283 (5)
C36	1.0334 (2)	−0.1482 (2)	0.86166 (17)	0.0370 (6)
H36A	1.1067	−0.1717	0.8196	0.044*
C37	1.0441 (2)	−0.1489 (2)	0.94604 (19)	0.0414 (6)
H37A	1.1241	−0.1726	0.9597	0.050*
C38	0.9367 (2)	−0.1145 (2)	1.00936 (17)	0.0343 (5)
H38A	0.9438	−0.1161	1.0660	0.041*
C39	0.8190 (2)	−0.0779 (2)	0.98804 (15)	0.0320 (5)
H39A	0.7462	−0.0532	1.0301	0.038*
C40	0.8079 (2)	−0.0776 (2)	0.90389 (15)	0.0299 (5)
H40A	0.7277	−0.0535	0.8905	0.036*
O5	0.39349 (18)	1.03378 (16)	0.68444 (12)	0.0399 (4)
H5B	0.3819	0.9842	0.6619	0.048*
H5C	0.4245	1.0861	0.6352	0.048*
O6	0.35322 (16)	0.87072 (14)	0.61361 (12)	0.0356 (4)
H6B	0.3705	0.7956	0.6428	0.043*
H6C	0.2684	0.8806	0.6087	0.043*
O7	1.14845 (15)	−0.11805 (14)	0.55998 (10)	0.0307 (3)
H7B	1.0657	−0.0635	0.5770	0.037*
H7C	1.1480	−0.1006	0.5005	0.037*
O8	0.52945 (16)	0.78513 (16)	0.46170 (11)	0.0351 (4)
H8B	0.4871	0.8222	0.5025	0.042*
H8C	0.4789	0.7740	0.4378	0.042*
O9	0.54855 (19)	−0.03208 (19)	0.80451 (11)	0.0478 (5)
H9B	0.5011	−0.0164	0.7692	0.057*
H9C	0.6005	−0.0017	0.7841	0.057*
O10	0.64854 (14)	0.27146 (13)	0.58757 (9)	0.0261 (3)
H10B	0.6377	0.3379	0.6076	0.031*
H10C	0.6953	0.2065	0.6203	0.031*

	U11	U22	U33	U12	U13	U23
Cu	0.01848 (13)	0.01903 (12)	0.01421 (11)	−0.01010 (9)	−0.00353 (9)	0.00032 (9)
N1	0.0194 (8)	0.0230 (8)	0.0198 (8)	−0.0072 (7)	−0.0056 (7)	−0.0048 (7)
N2	0.0204 (8)	0.0226 (8)	0.0146 (7)	−0.0111 (7)	−0.0037 (6)	−0.0010 (7)
C1	0.0251 (11)	0.0232 (10)	0.0267 (10)	−0.0075 (9)	−0.0077 (9)	−0.0048 (9)
C2	0.0268 (11)	0.0281 (11)	0.0364 (12)	−0.0003 (9)	−0.0133 (10)	−0.0123 (10)
C3	0.0190 (10)	0.0410 (13)	0.0285 (11)	−0.0049 (9)	−0.0070 (9)	−0.0158 (10)
C4	0.0196 (10)	0.0378 (12)	0.0194 (9)	−0.0108 (9)	−0.0043 (8)	−0.0127 (9)
C5	0.0195 (10)	0.0486 (14)	0.0180 (9)	−0.0175 (10)	−0.0001 (8)	−0.0123 (10)
C6	0.0274 (11)	0.0469 (13)	0.0165 (9)	−0.0255 (10)	−0.0008 (8)	−0.0057 (9)
C7	0.0266 (11)	0.0336 (11)	0.0131 (8)	−0.0187 (9)	−0.0036 (8)	−0.0032 (8)
C8	0.0375 (12)	0.0311 (11)	0.0178 (9)	−0.0242 (10)	−0.0061 (9)	0.0015 (9)
C9	0.0346 (12)	0.0238 (10)	0.0233 (10)	−0.0147 (9)	−0.0096 (9)	0.0017 (9)
C10	0.0252 (11)	0.0233 (10)	0.0206 (9)	−0.0105 (8)	−0.0060 (8)	−0.0013 (8)
C11	0.0214 (10)	0.0280 (10)	0.0126 (8)	−0.0123 (8)	−0.0046 (7)	−0.0048 (8)
C12	0.0202 (10)	0.0272 (10)	0.0145 (8)	−0.0106 (8)	−0.0047 (7)	−0.0054 (8)
N3	0.0163 (8)	0.0219 (8)	0.0181 (8)	−0.0073 (7)	−0.0038 (6)	−0.0039 (7)
N4	0.0175 (8)	0.0192 (8)	0.0169 (7)	−0.0076 (7)	−0.0032 (6)	−0.0018 (7)
C13	0.0219 (10)	0.0255 (10)	0.0235 (10)	−0.0113 (8)	−0.0045 (8)	−0.0022 (9)
C14	0.0246 (11)	0.0327 (11)	0.0336 (11)	−0.0123 (9)	−0.0065 (9)	−0.0137 (10)
C15	0.0223 (11)	0.0344 (12)	0.0261 (10)	−0.0031 (9)	−0.0073 (9)	−0.0145 (10)
C16	0.0161 (9)	0.0265 (10)	0.0183 (9)	−0.0016 (8)	−0.0026 (7)	−0.0067 (8)
C17	0.0234 (11)	0.0313 (11)	0.0159 (9)	−0.0018 (9)	−0.0042 (8)	−0.0048 (9)
C18	0.0226 (10)	0.0280 (11)	0.0161 (9)	−0.0039 (9)	−0.0012 (8)	0.0001 (8)
C19	0.0161 (9)	0.0205 (9)	0.0172 (9)	−0.0027 (8)	−0.0012 (7)	−0.0001 (8)
C20	0.0210 (10)	0.0187 (9)	0.0222 (10)	−0.0065 (8)	−0.0009 (8)	0.0040 (8)
C21	0.0236 (11)	0.0204 (10)	0.0282 (10)	−0.0101 (8)	−0.0054 (9)	−0.0017 (9)
C22	0.0227 (10)	0.0236 (10)	0.0205 (9)	−0.0090 (8)	−0.0046 (8)	−0.0039 (8)
C23	0.0131 (9)	0.0184 (9)	0.0148 (8)	−0.0026 (7)	−0.0025 (7)	−0.0012 (7)
C24	0.0132 (9)	0.0201 (9)	0.0174 (9)	−0.0015 (7)	−0.0035 (7)	−0.0038 (8)
O1	0.0204 (7)	0.0212 (7)	0.0170 (6)	−0.0089 (6)	−0.0052 (5)	−0.0010 (6)
O2	0.0237 (7)	0.0284 (7)	0.0179 (6)	−0.0100 (6)	−0.0019 (6)	−0.0076 (6)
C25	0.0195 (10)	0.0213 (9)	0.0107 (8)	−0.0101 (8)	−0.0012 (7)	0.0016 (7)
C26	0.0199 (10)	0.0236 (10)	0.0155 (9)	−0.0066 (8)	−0.0056 (7)	−0.0030 (8)
C27	0.0194 (10)	0.0228 (9)	0.0162 (8)	−0.0084 (8)	−0.0084 (7)	−0.0019 (8)
C28	0.0211 (10)	0.0230 (10)	0.0231 (10)	−0.0075 (8)	−0.0059 (8)	−0.0034 (8)
C29	0.0183 (10)	0.0347 (12)	0.0275 (10)	−0.0077 (9)	−0.0032 (8)	−0.0095 (9)
C30	0.0255 (11)	0.0383 (12)	0.0211 (10)	−0.0202 (10)	−0.0038 (8)	−0.0007 (9)
C31	0.0356 (12)	0.0244 (10)	0.0251 (10)	−0.0168 (9)	−0.0131 (9)	0.0034 (9)
C32	0.0239 (10)	0.0225 (10)	0.0229 (10)	−0.0058 (8)	−0.0089 (8)	−0.0048 (8)
O3	0.0261 (8)	0.0244 (8)	0.0299 (8)	−0.0068 (6)	−0.0034 (6)	0.0023 (7)
O4	0.0313 (9)	0.0238 (8)	0.0272 (8)	−0.0068 (7)	−0.0010 (7)	0.0023 (6)
C33	0.0302 (11)	0.0166 (9)	0.0239 (10)	−0.0085 (9)	−0.0076 (9)	−0.0001 (8)
C34	0.0529 (16)	0.0179 (10)	0.0274 (11)	−0.0038 (10)	−0.0079 (11)	−0.0012 (9)
C35	0.0354 (12)	0.0139 (9)	0.0286 (11)	−0.0048 (9)	−0.0056 (9)	0.0006 (9)
C36	0.0304 (13)	0.0282 (12)	0.0446 (14)	−0.0035 (10)	−0.0012 (11)	−0.0101 (11)
C37	0.0309 (13)	0.0395 (14)	0.0561 (16)	−0.0032 (11)	−0.0164 (12)	−0.0156 (13)
C38	0.0400 (14)	0.0268 (11)	0.0363 (12)	−0.0072 (10)	−0.0150 (11)	−0.0041 (10)
C39	0.0330 (12)	0.0288 (11)	0.0256 (11)	−0.0069 (10)	−0.0035 (9)	−0.0002 (9)
C40	0.0274 (11)	0.0268 (11)	0.0275 (11)	−0.0052 (9)	−0.0078 (9)	0.0026 (9)
O5	0.0506 (11)	0.0361 (9)	0.0412 (9)	−0.0205 (8)	−0.0180 (8)	−0.0034 (8)
O6	0.0385 (9)	0.0259 (8)	0.0460 (10)	−0.0092 (7)	−0.0167 (8)	−0.0065 (7)
O7	0.0279 (8)	0.0314 (8)	0.0277 (8)	−0.0047 (7)	−0.0064 (6)	−0.0044 (7)
O8	0.0335 (9)	0.0430 (10)	0.0340 (8)	−0.0173 (8)	−0.0045 (7)	−0.0114 (8)
O9	0.0638 (13)	0.0678 (13)	0.0242 (8)	−0.0491 (11)	−0.0145 (8)	0.0113 (8)
O10	0.0317 (8)	0.0221 (7)	0.0245 (7)	−0.0073 (6)	−0.0095 (6)	−0.0031 (6)

Cu—N2	2.0009 (18)	C21—H21A	0.9300
Cu—O1	2.0011 (14)	C22—H22A	0.9300
Cu—N4	2.0128 (17)	C23—C24	1.430 (3)
Cu—N3	2.0600 (16)	O1—C25	1.281 (2)
Cu—N1	2.1866 (19)	O2—C25	1.247 (2)
N1—C1	1.330 (3)	C25—C26	1.522 (3)
N1—C12	1.357 (3)	C26—C27	1.517 (3)
N2—C10	1.336 (3)	C26—H26A	0.9700
N2—C11	1.365 (3)	C26—H26B	0.9700
C1—C2	1.405 (3)	C27—C28	1.388 (3)
C1—H1A	0.9300	C27—C32	1.395 (3)
C2—C3	1.366 (3)	C28—C29	1.389 (3)
C2—H2A	0.9300	C28—H28A	0.9300
C3—C4	1.408 (3)	C29—C30	1.393 (3)
C3—H3A	0.9300	C29—H29A	0.9300
C4—C12	1.404 (3)	C30—C31	1.387 (3)
C4—C5	1.441 (3)	C30—H30A	0.9300
C5—C6	1.347 (3)	C31—C32	1.391 (3)
C5—H5A	0.9300	C31—H31A	0.9300
C6—C7	1.434 (3)	C32—H32A	0.9300
C6—H6A	0.9300	O3—C33	1.250 (3)
C7—C8	1.407 (3)	O4—C33	1.254 (3)
C7—C11	1.410 (3)	C33—C34	1.536 (3)
C8—C9	1.366 (3)	C34—C35	1.513 (3)
C8—H8A	0.9300	C34—H34A	0.9700
C9—C10	1.403 (3)	C34—H34B	0.9700
C9—H9A	0.9300	C35—C36	1.382 (3)
C10—H10A	0.9300	C35—C40	1.395 (3)
C11—C12	1.441 (3)	C36—C37	1.394 (4)
N3—C13	1.327 (3)	C36—H36A	0.9300
N3—C24	1.365 (3)	C37—C38	1.378 (4)
N4—C22	1.329 (2)	C37—H37A	0.9300
N4—C23	1.367 (2)	C38—C39	1.375 (3)
C13—C14	1.402 (3)	C38—H38A	0.9300
C13—H13A	0.9300	C39—C40	1.393 (3)
C14—C15	1.373 (3)	C39—H39A	0.9300
C14—H14A	0.9300	C40—H40A	0.9300
C15—C16	1.409 (3)	O5—H5B	0.8492
C15—H15A	0.9300	O5—H5C	0.9025
C16—C24	1.401 (3)	O6—H6B	0.8443
C16—C17	1.429 (3)	O6—H6C	0.9634
C17—C18	1.359 (3)	O7—H7B	0.9596
C17—H17A	0.9300	O7—H7C	0.9107
C18—C19	1.438 (3)	O8—H8B	0.8418
C18—H18A	0.9300	O8—H8C	0.8508
C19—C23	1.404 (3)	O9—H9B	0.8328
C19—C20	1.410 (3)	O9—H9C	0.7473
C20—C21	1.371 (3)	O10—H10B	0.9033
C20—H20A	0.9300	O10—H10C	0.8749
C21—C22	1.404 (3)
N2—Cu—O1	95.38 (6)	C20—C19—C18	124.14 (18)
N2—Cu—N4	173.84 (6)	C21—C20—C19	119.44 (18)
O1—Cu—N4	90.11 (6)	C21—C20—H20A	120.3
N2—Cu—N3	92.59 (7)	C19—C20—H20A	120.3
O1—Cu—N3	159.85 (6)	C20—C21—C22	119.49 (19)
N4—Cu—N3	81.31 (7)	C20—C21—H21A	120.3
N2—Cu—N1	80.25 (7)	C22—C21—H21A	120.3
O1—Cu—N1	99.99 (6)	N4—C22—C21	122.70 (18)
N4—Cu—N1	101.58 (7)	N4—C22—H22A	118.7
N3—Cu—N1	99.58 (7)	C21—C22—H22A	118.7
C1—N1—C12	118.02 (18)	N4—C23—C19	123.02 (18)
C1—N1—Cu	132.56 (14)	N4—C23—C24	116.59 (16)
C12—N1—Cu	109.42 (13)	C19—C23—C24	120.39 (17)
C10—N2—C11	118.72 (17)	N3—C24—C16	123.45 (18)
C10—N2—Cu	126.25 (14)	N3—C24—C23	116.65 (17)
C11—N2—Cu	114.99 (13)	C16—C24—C23	119.90 (18)
N1—C1—C2	122.3 (2)	C25—O1—Cu	108.11 (12)
N1—C1—H1A	118.8	O2—C25—O1	122.11 (18)
C2—C1—H1A	118.8	O2—C25—C26	119.94 (18)
C3—C2—C1	119.9 (2)	O1—C25—C26	117.82 (17)
C3—C2—H2A	120.1	C27—C26—C25	108.99 (15)
C1—C2—H2A	120.1	C27—C26—H26A	109.9
C2—C3—C4	119.2 (2)	C25—C26—H26A	109.9
C2—C3—H3A	120.4	C27—C26—H26B	109.9
C4—C3—H3A	120.4	C25—C26—H26B	109.9
C12—C4—C3	117.3 (2)	H26A—C26—H26B	108.3
C12—C4—C5	119.5 (2)	C28—C27—C32	119.05 (19)
C3—C4—C5	123.19 (19)	C28—C27—C26	120.48 (18)
C6—C5—C4	121.05 (19)	C32—C27—C26	120.47 (18)
C6—C5—H5A	119.5	C27—C28—C29	120.5 (2)
C4—C5—H5A	119.5	C27—C28—H28A	119.8
C5—C6—C7	121.2 (2)	C29—C28—H28A	119.8
C5—C6—H6A	119.4	C28—C29—C30	120.6 (2)
C7—C6—H6A	119.4	C28—C29—H29A	119.7
C8—C7—C11	117.52 (19)	C30—C29—H29A	119.7
C8—C7—C6	123.42 (19)	C31—C30—C29	118.83 (19)
C11—C7—C6	119.0 (2)	C31—C30—H30A	120.6
C9—C8—C7	119.88 (19)	C29—C30—H30A	120.6
C9—C8—H8A	120.1	C30—C31—C32	120.7 (2)
C7—C8—H8A	120.1	C30—C31—H31A	119.6
C8—C9—C10	119.5 (2)	C32—C31—H31A	119.6
C8—C9—H9A	120.3	C31—C32—C27	120.3 (2)
C10—C9—H9A	120.3	C31—C32—H32A	119.9
N2—C10—C9	122.2 (2)	C27—C32—H32A	119.9
N2—C10—H10A	118.9	O3—C33—O4	124.60 (19)
C9—C10—H10A	118.9	O3—C33—C34	118.50 (19)
N2—C11—C7	122.18 (19)	O4—C33—C34	116.88 (19)
N2—C11—C12	117.75 (17)	C35—C34—C33	114.35 (18)
C7—C11—C12	120.06 (18)	C35—C34—H34A	108.7
N1—C12—C4	123.28 (19)	C33—C34—H34A	108.7
N1—C12—C11	117.49 (17)	C35—C34—H34B	108.7
C4—C12—C11	119.20 (18)	C33—C34—H34B	108.7
C13—N3—C24	117.51 (17)	H34A—C34—H34B	107.6
C13—N3—Cu	130.54 (14)	C36—C35—C40	118.0 (2)
C24—N3—Cu	111.93 (12)	C36—C35—C34	121.2 (2)
C22—N4—C23	118.00 (17)	C40—C35—C34	120.9 (2)
C22—N4—Cu	128.52 (13)	C35—C36—C37	121.2 (2)
C23—N4—Cu	113.47 (12)	C35—C36—H36A	119.4
N3—C13—C14	123.11 (19)	C37—C36—H36A	119.4
N3—C13—H13A	118.4	C38—C37—C36	120.3 (2)
C14—C13—H13A	118.4	C38—C37—H37A	119.8
C15—C14—C13	119.33 (19)	C36—C37—H37A	119.8
C15—C14—H14A	120.3	C39—C38—C37	119.4 (2)
C13—C14—H14A	120.3	C39—C38—H38A	120.3
C14—C15—C16	119.35 (19)	C37—C38—H38A	120.3
C14—C15—H15A	120.3	C38—C39—C40	120.5 (2)
C16—C15—H15A	120.3	C38—C39—H39A	119.8
C24—C16—C15	117.25 (19)	C40—C39—H39A	119.8
C24—C16—C17	119.03 (19)	C39—C40—C35	120.8 (2)
C15—C16—C17	123.72 (19)	C39—C40—H40A	119.6
C18—C17—C16	121.23 (19)	C35—C40—H40A	119.6
C18—C17—H17A	119.4	H5B—O5—H5C	102.2
C16—C17—H17A	119.4	H6B—O6—H6C	97.9
C17—C18—C19	120.92 (19)	H7B—O7—H7C	97.3
C17—C18—H18A	119.5	H8B—O8—H8C	109.3
C19—C18—H18A	119.5	H9B—O9—H9C	112.4
C23—C19—C20	117.33 (18)	H10B—O10—H10C	107.4
C23—C19—C18	118.53 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5B···O6	0.849	1.920	2.769 (3)	178.64
O5—H5C···O8i	0.902	1.898	2.794 (3)	171.66
O6—H6B···O2	0.844	1.912	2.723 (2)	160.78
O6—H6C···O7ii	0.963	1.767	2.682 (3)	157.25
O7—H7B···O3	0.960	1.754	2.710 (2)	173.79
O7—H7C···O3iii	0.911	2.028	2.896 (2)	158.83
O8—H8B···O6	0.842	2.076	2.888 (3)	161.67
O8—H8C···O10iv	0.851	1.915	2.749 (3)	166.41
O9—H9B···O5v	0.833	1.915	2.746 (3)	175.07
O9—H9C···O4	0.747	2.046	2.790 (3)	173.58
O10—H10B···O1	0.903	1.911	2.812 (2)	175.12
O10—H10C···O4	0.875	1.842	2.686 (2)	161.44