Tetra-kis[μ-2-(3-phenoxy-phen-yl)propionato-κO:O']bis-[(dimethyl-formamide-κO)copper(II)].

The title compound, [Cu(2)(C(15)H(13)O(3))(4)(C(3)H(7)NO)(2)], is formed by the chelate coordination of four racemic fenoprofenate (fenoprofenate is 2,3-phenoxyphenyl propionate) anions and two dimethyl-formamide mol-ecules to two copper(II) ions, building a paddle-wheel dinuclear mol-ecule. The distorted square-pyramidal coordination of each Cu(II) atom is made up of four O atoms of the four fenoprofenate units and another O atom from a dimethyl-formamide mol-ecule. The two enanti-omeric forms of the fenoprofenate anions are present in the complex, in an optically inactive centrosymmetric arrangement.

Related literature

For the properties of fenoprofen, see: Brogden et al. (1977 ▶); Nickander et al. (1977 ▶); Weder et al. (2002 ▶). For fenoprofen structures, see: Hamilton & Chen (1988a ▶,b ▶); Stephenson & Diseroad (2000 ▶); Weder et al. (2002 ▶); Zhu et al. (2001 ▶).

Experimental

Crystal data

[Cu2(C15H13O3)4(C3H7NO)2]

M = 1238.29

Monoclinic,

a = 11.142 (8) Å

b = 11.580 (8) Å

c = 23.891 (6) Å

β = 99.85 (6)°

V = 3037 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.77 mm−1

T = 293 (2) K

0.20 × 0.20 × 0.10 mm

Data collection

Rigaku AFC-7S diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.862, T max = 0.927

8818 measured reflections

6969 independent reflections

4101 reflections with I > 2σ(I)

R int = 0.091

3 standard reflections every 150 reflections intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.200

S = 1.02

6969 reflections

381 parameters

H-atom parameters constrained

Δρmax = 0.51 e Å−3

Δρmin = −0.54 e Å−3

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993 ▶); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: MSC/AFC Diffractometer Control Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808038786/bg2218sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808038786/bg2218Isup2.hkl

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

[Cu2(C15H13O3)4(C3H7NO)2]	F000 = 1292
Mr = 1238.29	Dx = 1.354 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 50 reflections
a = 11.142 (8) Å	θ = 5.1–13.6º
b = 11.580 (8) Å	µ = 0.77 mm−1
c = 23.891 (6) Å	T = 293 (2) K
β = 99.85 (6)º	Plate, green
V = 3037 (3) Å3	0.20 × 0.20 × 0.10 mm
Z = 2

Rigaku AFC-7S diffractometer	Rint = 0.091
Radiation source: fine-focus sealed tube	θmax = 27.5º
Monochromator: graphite	θmin = 2.3º
T = 293(2) K	h = −1→14
θ/2θ scans	k = −1→15
Absorption correction: ψ scan(North et al., 1968)	l = −31→30
Tmin = 0.862, Tmax = 0.927	3 standard reflections
8818 measured reflections	every 150 reflections
6969 independent reflections	intensity decay: none
4101 reflections with I > 2σ(I)

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.064	H-atom parameters constrained
wR(F2) = 0.200	w = 1/[σ2(Fo2) + (0.0755P)2 + 0.3252P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
6969 reflections	Δρmax = 0.51 e Å−3
381 parameters	Δρmin = −0.54 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq
C11	0.5569 (6)	1.1752 (5)	−0.0520 (2)	0.0417 (15)
C12	0.5867 (6)	1.2834 (6)	−0.0844 (3)	0.0546 (17)
H12	0.5103	1.3066	−0.1084	0.066*
C13	0.6736 (8)	1.2579 (7)	−0.1238 (3)	0.093 (3)
H13A	0.6440	1.1936	−0.1476	0.139*
H13B	0.7520	1.2393	−0.1022	0.139*
H13C	0.6808	1.3244	−0.1470	0.139*
C14	0.6237 (5)	1.3829 (5)	−0.0446 (2)	0.0391 (13)
C15	0.5925 (5)	1.4966 (5)	−0.0623 (3)	0.0511 (17)
H15	0.5477	1.5090	−0.0983	0.061*
C16	0.6263 (6)	1.5889 (6)	−0.0277 (3)	0.0599 (19)
H16	0.6059	1.6631	−0.0409	0.072*
C17	0.6902 (6)	1.5738 (6)	0.0264 (4)	0.061 (2)
H17	0.7133	1.6368	0.0499	0.073*
C18	0.7191 (5)	1.4632 (6)	0.0449 (3)	0.0501 (15)
C19	0.6876 (5)	1.3686 (5)	0.0097 (3)	0.0413 (14)
H19	0.7098	1.2948	0.0230	0.050*
C20	0.9021 (5)	1.4495 (5)	0.1130 (3)	0.0461 (15)
C21	0.9731 (6)	1.4870 (7)	0.0754 (3)	0.066 (2)
H21	0.9375	1.5124	0.0395	0.079*
C22	1.0966 (6)	1.4868 (9)	0.0911 (3)	0.095 (3)
H22	1.1453	1.5098	0.0652	0.114*
C23	1.1509 (7)	1.4529 (8)	0.1453 (4)	0.088 (3)
H23	1.2353	1.4540	0.1557	0.106*
C24	1.0802 (7)	1.4184 (7)	0.1828 (3)	0.071 (2)
H24	1.1159	1.3953	0.2191	0.085*
C25	0.9548 (6)	1.4174 (6)	0.1672 (3)	0.0572 (17)
H25	0.9061	1.3951	0.1933	0.069*
C31	0.5588 (6)	1.0976 (6)	0.0955 (2)	0.0477 (15)
C32	0.5866 (6)	1.1560 (7)	0.1538 (3)	0.062 (2)
H32	0.5509	1.2335	0.1490	0.075*
C33	0.7150 (8)	1.1719 (9)	0.1752 (3)	0.109 (4)
H33A	0.7515	1.2141	0.1479	0.163*
H33B	0.7537	1.0979	0.1817	0.163*
H33C	0.7250	1.2142	0.2102	0.163*
C34	0.5154 (6)	1.0908 (7)	0.1932 (3)	0.0566 (17)
C35	0.3948 (6)	1.1190 (7)	0.1930 (3)	0.0602 (19)
H35	0.3581	1.1753	0.1679	0.072*
C36	0.3279 (6)	1.0659 (8)	0.2289 (3)	0.071 (2)
C37	0.3784 (8)	0.9814 (9)	0.2655 (3)	0.092 (3)
H37	0.3338	0.9470	0.2906	0.111*
C38	0.4965 (8)	0.9486 (9)	0.2645 (4)	0.097 (3)
H38	0.5312	0.8889	0.2878	0.116*
C39	0.5636 (7)	1.0035 (7)	0.2291 (3)	0.074 (2)
H39	0.6439	0.9809	0.2295	0.088*
C40	0.1689 (6)	1.1642 (7)	0.2655 (3)	0.0594 (18)
C41	0.2497 (7)	1.2272 (7)	0.3036 (3)	0.074 (2)
H41	0.3331	1.2224	0.3037	0.089*
C42	0.2046 (10)	1.2973 (8)	0.3415 (3)	0.095 (3)
H42	0.2578	1.3406	0.3676	0.114*
C43	0.0822 (11)	1.3038 (10)	0.3410 (4)	0.108 (4)
H43	0.0522	1.3519	0.3665	0.129*
C44	0.0026 (8)	1.2392 (9)	0.3027 (4)	0.088 (3)
H44	−0.0806	1.2425	0.3031	0.106*
C45	0.0460 (7)	1.1709 (7)	0.2645 (3)	0.068 (2)
H45	−0.0074	1.1290	0.2379	0.082*
C51	0.8413 (6)	0.9038 (6)	−0.0378 (3)	0.0563 (17)
H51	0.7959	0.9392	−0.0694	0.068*
C53	1.0207 (7)	0.8041 (8)	0.0057 (3)	0.094 (3)
H53A	1.0998	0.8390	0.0148	0.141*
H53B	1.0293	0.7246	−0.0044	0.141*
H53C	0.9804	0.8086	0.0380	0.141*
C54	1.0004 (8)	0.8783 (9)	−0.0945 (3)	0.098 (3)
H54A	0.9425	0.9156	−0.1231	0.147*
H54B	1.0199	0.8034	−0.1077	0.147*
H54C	1.0732	0.9241	−0.0866	0.147*
Cu1	0.61251 (6)	0.96206 (6)	0.00433 (3)	0.0391 (2)
O11	0.6419 (4)	1.1044 (4)	−0.03595 (19)	0.0546 (12)
O12	0.4481 (4)	1.1667 (3)	−0.04371 (17)	0.0468 (10)
O13	0.7767 (4)	1.4439 (4)	0.10133 (18)	0.0607 (13)
O31	0.6426 (4)	1.0452 (4)	0.07660 (17)	0.0529 (10)
O32	0.4517 (4)	1.1100 (4)	0.06887 (18)	0.0536 (11)
O33	0.2043 (4)	1.0911 (6)	0.2244 (2)	0.095 (2)
O51	0.7945 (4)	0.8967 (4)	0.00567 (19)	0.0579 (12)
N52	0.9482 (5)	0.8656 (5)	−0.0425 (3)	0.0612 (16)

	U11	U22	U33	U12	U13	U23
C11	0.064 (4)	0.032 (3)	0.029 (3)	−0.018 (3)	0.009 (3)	−0.001 (2)
C12	0.063 (4)	0.052 (4)	0.049 (4)	−0.013 (3)	0.011 (3)	0.008 (3)
C13	0.138 (8)	0.065 (5)	0.084 (6)	−0.028 (6)	0.046 (6)	0.014 (5)
C14	0.027 (3)	0.038 (3)	0.053 (4)	−0.001 (3)	0.009 (3)	0.007 (3)
C15	0.026 (3)	0.048 (4)	0.079 (5)	0.000 (3)	0.008 (3)	0.017 (3)
C16	0.050 (4)	0.038 (4)	0.092 (6)	0.001 (3)	0.013 (4)	0.009 (4)
C17	0.055 (4)	0.040 (4)	0.092 (6)	0.001 (3)	0.025 (4)	−0.009 (4)
C18	0.029 (3)	0.057 (4)	0.068 (4)	−0.007 (4)	0.019 (3)	−0.004 (4)
C19	0.025 (3)	0.038 (3)	0.062 (4)	0.003 (3)	0.011 (3)	0.009 (3)
C20	0.031 (3)	0.046 (4)	0.061 (4)	−0.009 (3)	0.007 (3)	−0.004 (3)
C21	0.041 (3)	0.092 (6)	0.061 (4)	−0.011 (4)	0.001 (3)	0.014 (4)
C22	0.043 (4)	0.170 (10)	0.074 (5)	−0.021 (5)	0.018 (4)	0.034 (6)
C23	0.045 (4)	0.123 (8)	0.088 (6)	−0.001 (5)	−0.010 (4)	0.024 (6)
C24	0.066 (5)	0.070 (5)	0.070 (5)	−0.002 (4)	−0.005 (4)	0.022 (4)
C25	0.059 (4)	0.057 (4)	0.057 (4)	−0.011 (3)	0.011 (3)	0.001 (3)
C31	0.058 (4)	0.053 (4)	0.033 (3)	−0.020 (4)	0.012 (3)	−0.005 (3)
C32	0.058 (4)	0.084 (5)	0.048 (4)	−0.020 (4)	0.017 (3)	−0.020 (4)
C33	0.113 (8)	0.145 (9)	0.067 (6)	−0.066 (7)	0.013 (5)	−0.019 (6)
C34	0.061 (4)	0.069 (4)	0.039 (4)	−0.009 (4)	0.005 (3)	−0.013 (3)
C35	0.065 (4)	0.078 (5)	0.036 (4)	0.000 (4)	0.002 (3)	−0.008 (3)
C36	0.052 (4)	0.111 (7)	0.050 (4)	0.011 (4)	0.009 (4)	−0.013 (4)
C37	0.074 (5)	0.141 (9)	0.065 (5)	0.002 (6)	0.023 (4)	0.036 (6)
C38	0.076 (6)	0.124 (9)	0.090 (6)	0.014 (6)	0.016 (5)	0.032 (6)
C39	0.054 (4)	0.095 (6)	0.076 (5)	0.007 (4)	0.021 (4)	0.002 (5)
C40	0.050 (4)	0.074 (5)	0.054 (4)	−0.002 (4)	0.006 (3)	0.009 (4)
C41	0.064 (5)	0.091 (6)	0.062 (5)	0.000 (5)	−0.004 (4)	0.007 (5)
C42	0.117 (8)	0.097 (7)	0.063 (6)	0.011 (6)	−0.007 (5)	−0.003 (5)
C43	0.136 (9)	0.123 (9)	0.072 (6)	0.044 (8)	0.040 (7)	−0.008 (6)
C44	0.082 (6)	0.112 (8)	0.075 (6)	0.019 (6)	0.023 (5)	0.012 (6)
C45	0.059 (4)	0.081 (5)	0.067 (5)	0.000 (4)	0.015 (4)	0.005 (4)
C51	0.043 (4)	0.063 (4)	0.060 (4)	0.002 (4)	0.002 (3)	−0.002 (4)
C53	0.063 (5)	0.108 (7)	0.111 (7)	0.041 (5)	0.015 (5)	0.015 (6)
C54	0.091 (6)	0.122 (8)	0.092 (6)	0.009 (6)	0.047 (5)	−0.012 (6)
Cu1	0.0343 (3)	0.0397 (4)	0.0429 (4)	0.0012 (4)	0.0060 (3)	−0.0011 (4)
O11	0.037 (2)	0.047 (3)	0.081 (3)	0.001 (2)	0.013 (2)	0.012 (2)
O12	0.043 (2)	0.037 (2)	0.061 (3)	−0.0041 (19)	0.010 (2)	0.013 (2)
O13	0.039 (2)	0.085 (4)	0.058 (3)	−0.014 (2)	0.010 (2)	−0.009 (3)
O31	0.049 (2)	0.058 (3)	0.051 (2)	−0.008 (2)	0.004 (2)	−0.013 (2)
O32	0.046 (2)	0.062 (3)	0.052 (3)	−0.004 (2)	0.003 (2)	−0.011 (2)
O33	0.056 (3)	0.147 (6)	0.082 (4)	0.005 (3)	0.009 (3)	−0.042 (4)
O51	0.042 (2)	0.071 (3)	0.062 (3)	0.018 (2)	0.014 (2)	0.004 (3)
N52	0.038 (3)	0.069 (4)	0.080 (4)	0.008 (3)	0.022 (3)	−0.017 (3)

C11—O11	1.261 (7)	C34—C35	1.382 (9)
C11—O12	1.265 (7)	C35—C36	1.375 (9)
C11—C12	1.538 (8)	C35—H35	0.9300
C12—C13	1.491 (9)	C36—C37	1.368 (11)
C12—C14	1.505 (8)	C36—O33	1.393 (8)
C12—H12	0.9800	C37—C38	1.374 (11)
C13—H13A	0.9600	C37—H37	0.9300
C13—H13B	0.9600	C38—C39	1.378 (10)
C13—H13C	0.9600	C38—H38	0.9300
C14—C19	1.381 (8)	C39—H39	0.9300
C14—C15	1.407 (8)	C40—C45	1.368 (9)
C15—C16	1.364 (9)	C40—C41	1.375 (10)
C15—H15	0.9300	C40—O33	1.403 (8)
C16—C17	1.377 (10)	C41—C42	1.374 (11)
C16—H16	0.9300	C41—H41	0.9300
C17—C18	1.375 (9)	C42—C43	1.364 (12)
C17—H17	0.9300	C42—H42	0.9300
C18—C19	1.388 (8)	C43—C44	1.379 (12)
C18—O13	1.408 (7)	C43—H43	0.9300
C19—H19	0.9300	C44—C45	1.357 (10)
C20—C21	1.364 (9)	C44—H44	0.9300
C20—O13	1.379 (7)	C45—H45	0.9300
C20—C25	1.379 (8)	C51—O51	1.241 (7)
C21—C22	1.364 (9)	C51—N52	1.293 (8)
C21—H21	0.9300	C51—H51	0.9300
C22—C23	1.388 (10)	C53—N52	1.472 (9)
C22—H22	0.9300	C53—H53A	0.9600
C23—C24	1.351 (10)	C53—H53B	0.9600
C23—H23	0.9300	C53—H53C	0.9600
C24—C25	1.383 (10)	C54—N52	1.465 (8)
C24—H24	0.9300	C54—H54A	0.9600
C25—H25	0.9300	C54—H54B	0.9600
C31—O31	1.260 (7)	C54—H54C	0.9600
C31—O32	1.260 (7)	Cu1—O12i	1.945 (4)
C31—C32	1.533 (8)	Cu1—O31	1.955 (4)
C32—C33	1.446 (10)	Cu1—O32i	1.959 (4)
C32—C34	1.530 (9)	Cu1—O11	1.964 (4)
C32—H32	0.9800	Cu1—O51	2.160 (4)
C33—H33A	0.9600	Cu1—Cu1i	2.631 (2)
C33—H33B	0.9600	O12—Cu1i	1.945 (4)
C33—H33C	0.9600	O32—Cu1i	1.959 (4)
C34—C39	1.373 (10)
O11—C11—O12	126.3 (5)	C34—C35—H35	119.3
O11—C11—C12	117.8 (5)	C37—C36—C35	120.8 (7)
O12—C11—C12	115.9 (6)	C37—C36—O33	119.5 (7)
C13—C12—C14	114.4 (6)	C35—C36—O33	119.5 (7)
C13—C12—C11	112.1 (6)	C36—C37—C38	118.5 (8)
C14—C12—C11	111.4 (5)	C36—C37—H37	120.8
C13—C12—H12	106.1	C38—C37—H37	120.8
C14—C12—H12	106.1	C37—C38—C39	120.4 (8)
C11—C12—H12	106.1	C37—C38—H38	119.8
C12—C13—H13A	109.5	C39—C38—H38	119.8
C12—C13—H13B	109.5	C34—C39—C38	121.8 (7)
H13A—C13—H13B	109.5	C34—C39—H39	119.1
C12—C13—H13C	109.5	C38—C39—H39	119.1
H13A—C13—H13C	109.5	C45—C40—C41	121.4 (8)
H13B—C13—H13C	109.5	C45—C40—O33	115.0 (7)
C19—C14—C15	117.0 (6)	C41—C40—O33	123.6 (7)
C19—C14—C12	122.9 (5)	C40—C41—C42	118.6 (8)
C15—C14—C12	120.0 (5)	C40—C41—H41	120.7
C16—C15—C14	121.6 (6)	C42—C41—H41	120.7
C16—C15—H15	119.2	C43—C42—C41	120.2 (9)
C14—C15—H15	119.2	C43—C42—H42	119.9
C15—C16—C17	120.9 (7)	C41—C42—H42	119.9
C15—C16—H16	119.5	C42—C43—C44	120.3 (9)
C17—C16—H16	119.5	C42—C43—H43	119.8
C18—C17—C16	118.4 (7)	C44—C43—H43	119.8
C18—C17—H17	120.8	C45—C44—C43	119.9 (9)
C16—C17—H17	120.8	C45—C44—H44	120.0
C17—C18—C19	121.3 (6)	C43—C44—H44	120.0
C17—C18—O13	119.9 (7)	C44—C45—C40	119.5 (8)
C19—C18—O13	118.7 (6)	C44—C45—H45	120.2
C14—C19—C18	120.7 (6)	C40—C45—H45	120.2
C14—C19—H19	119.6	O51—C51—N52	125.2 (7)
C18—C19—H19	119.6	O51—C51—H51	117.4
C21—C20—O13	124.3 (6)	N52—C51—H51	117.4
C21—C20—C25	120.1 (6)	N52—C53—H53A	109.5
O13—C20—C25	115.5 (5)	N52—C53—H53B	109.5
C22—C21—C20	119.3 (7)	H53A—C53—H53B	109.5
C22—C21—H21	120.3	N52—C53—H53C	109.5
C20—C21—H21	120.3	H53A—C53—H53C	109.5
C21—C22—C23	121.1 (7)	H53B—C53—H53C	109.5
C21—C22—H22	119.5	N52—C54—H54A	109.5
C23—C22—H22	119.5	N52—C54—H54B	109.5
C24—C23—C22	119.4 (7)	H54A—C54—H54B	109.5
C24—C23—H23	120.3	N52—C54—H54C	109.5
C22—C23—H23	120.3	H54A—C54—H54C	109.5
C23—C24—C25	120.0 (7)	H54B—C54—H54C	109.5
C23—C24—H24	120.0	O12i—Cu1—O31	88.38 (18)
C25—C24—H24	120.0	O12i—Cu1—O32i	90.05 (18)
C20—C25—C24	119.9 (6)	O31—Cu1—O32i	168.30 (17)
C20—C25—H25	120.0	O12i—Cu1—O11	168.87 (17)
C24—C25—H25	120.0	O31—Cu1—O11	90.08 (19)
O31—C31—O32	124.7 (5)	O32i—Cu1—O11	89.23 (19)
O31—C31—C32	119.4 (6)	O12i—Cu1—O51	97.32 (18)
O32—C31—C32	115.8 (6)	O31—Cu1—O51	98.09 (18)
C33—C32—C34	115.6 (6)	O32i—Cu1—O51	93.61 (18)
C33—C32—C31	114.3 (6)	O11—Cu1—O51	93.81 (17)
C34—C32—C31	107.2 (5)	O12i—Cu1—Cu1i	83.62 (13)
C33—C32—H32	106.4	O31—Cu1—Cu1i	85.52 (14)
C34—C32—H32	106.4	O32i—Cu1—Cu1i	82.78 (14)
C31—C32—H32	106.4	O11—Cu1—Cu1i	85.28 (13)
C32—C33—H33A	109.5	O51—Cu1—Cu1i	176.28 (13)
C32—C33—H33B	109.5	C11—O11—Cu1	121.0 (4)
H33A—C33—H33B	109.5	C11—O12—Cu1i	123.8 (4)
C32—C33—H33C	109.5	C20—O13—C18	117.8 (5)
H33A—C33—H33C	109.5	C31—O31—Cu1	121.9 (4)
H33B—C33—H33C	109.5	C31—O32—Cu1i	124.8 (4)
C39—C34—C35	116.9 (7)	C36—O33—C40	117.7 (6)
C39—C34—C32	124.0 (7)	C51—O51—Cu1	119.5 (4)
C35—C34—C32	119.1 (7)	C51—N52—C54	123.0 (7)
C36—C35—C34	121.5 (7)	C51—N52—C53	119.1 (6)
C36—C35—H35	119.3	C54—N52—C53	117.8 (6)
O11—C11—C12—C13	37.9 (8)	C32—C34—C39—C38	178.9 (7)
O12—C11—C12—C13	−142.6 (6)	C37—C38—C39—C34	−1.1 (14)
O11—C11—C12—C14	−91.8 (7)	C45—C40—C41—C42	0.5 (12)
O12—C11—C12—C14	87.8 (6)	O33—C40—C41—C42	179.1 (7)
C13—C12—C14—C19	−94.5 (7)	C40—C41—C42—C43	−0.1 (13)
C11—C12—C14—C19	33.9 (8)	C41—C42—C43—C44	0.5 (15)
C13—C12—C14—C15	85.9 (8)	C42—C43—C44—C45	−1.5 (15)
C11—C12—C14—C15	−145.7 (6)	C43—C44—C45—C40	1.9 (13)
C19—C14—C15—C16	1.5 (9)	C41—C40—C45—C44	−1.5 (12)
C12—C14—C15—C16	−178.8 (6)	O33—C40—C45—C44	179.9 (7)
C14—C15—C16—C17	−1.5 (10)	O12—C11—O11—Cu1	1.8 (8)
C15—C16—C17—C18	−0.1 (10)	C12—C11—O11—Cu1	−178.7 (4)
C16—C17—C18—C19	1.5 (9)	O12i—Cu1—O11—C11	−4.9 (13)
C16—C17—C18—O13	−175.5 (5)	O31—Cu1—O11—C11	−86.9 (5)
C15—C14—C19—C18	−0.1 (8)	O32i—Cu1—O11—C11	81.4 (5)
C12—C14—C19—C18	−179.7 (5)	O51—Cu1—O11—C11	175.0 (5)
C17—C18—C19—C14	−1.5 (8)	O11—C11—O12—Cu1i	−0.9 (8)
O13—C18—C19—C14	175.6 (4)	C12—C11—O12—Cu1i	179.6 (4)
O13—C20—C21—C22	−178.8 (8)	C21—C20—O13—C18	9.0 (10)
C25—C20—C21—C22	3.3 (12)	C25—C20—O13—C18	−173.0 (6)
C20—C21—C22—C23	−2.2 (14)	C17—C18—O13—C20	−87.2 (7)
C21—C22—C23—C24	0.7 (15)	C19—C18—O13—C20	95.8 (6)
C22—C23—C24—C25	−0.2 (14)	O32—C31—O31—Cu1	−5.8 (9)
C21—C20—C25—C24	−2.8 (11)	C32—C31—O31—Cu1	176.9 (4)
O13—C20—C25—C24	179.0 (7)	O12i—Cu1—O31—C31	−81.3 (5)
C23—C24—C25—C20	1.3 (12)	O32i—Cu1—O31—C31	1.1 (12)
O31—C31—C32—C33	16.0 (10)	O11—Cu1—O31—C31	87.7 (5)
O32—C31—C32—C33	−161.6 (7)	O51—Cu1—O31—C31	−178.4 (5)
O31—C31—C32—C34	−113.4 (7)	O31—C31—O32—Cu1i	6.3 (9)
O32—C31—C32—C34	69.0 (8)	C32—C31—O32—Cu1i	−176.2 (4)
C33—C32—C34—C39	−33.3 (11)	C37—C36—O33—C40	81.8 (10)
C31—C32—C34—C39	95.4 (8)	C35—C36—O33—C40	−103.9 (8)
C33—C32—C34—C35	147.4 (7)	C45—C40—O33—C36	−169.9 (7)
C31—C32—C34—C35	−84.0 (8)	C41—C40—O33—C36	11.5 (11)
C39—C34—C35—C36	2.9 (10)	N52—C51—O51—Cu1	−178.4 (5)
C32—C34—C35—C36	−177.7 (6)	O12i—Cu1—O51—C51	136.1 (5)
C34—C35—C36—C37	−1.2 (12)	O31—Cu1—O51—C51	−134.5 (5)
C34—C35—C36—O33	−175.4 (7)	O32i—Cu1—O51—C51	45.6 (5)
C35—C36—C37—C38	−1.8 (14)	O11—Cu1—O51—C51	−43.9 (5)
O33—C36—C37—C38	172.4 (8)	O51—C51—N52—C54	−178.6 (7)
C36—C37—C38—C39	2.9 (15)	O51—C51—N52—C53	2.8 (11)
C35—C34—C39—C38	−1.8 (12)