Acta Cryst. (2012). E68, m350 [ doi:10.1107/S1600536812007064 ]
![[mu]](/logos/entities/mu_rmgif.gif)
-naphthalene-1-acetato-![[kappa]](/logos/entities/kappa_rmgif.gif)
2O:O')bis[(N,N-dimethylformamide-O)copper(II)]The asymmetric unit of the title compound, [Cu2(C12H9O2)4(C3H7NO)2], contains two independent centrosymmetric dinuclear copper(II) complexes. The central paddle-wheel units are formed by four bridging bidentate naphthalene-1-acetate ligands with two dimethylformamide ligands in the axial positions. The unique CuII ions have slightly distorted square-pyramidal coordination geometries. One of the naphthalene rings is disordered over two sets of sites, with refined occpancies of 0.535 (4) and 0.465 (4).
The title compound was synthesized by the reaction of Cu(NO3)2 × 3 H2O (72.3 mg, 0.3 mmol), naphthalene-1-yl-acetic acid (93 mg, 0.5 mmol), and NaOH (20 mg, 0.5 mmol) in 10 ml of N,N-dimethylformamide under solvothermal conditions. The mixture was homogenized and transferred into a sealed Teflon-lined solvothermal bomb (volume: 25 ml) and heated to 423K for three days. After cooling green crystals of the title compound were obtained, which were washed with distilled water and absolute ethanol (yield: 48.5% based on Cu(NO3)2 × 3 H2O).
H atoms were placed in calculated positions, with C—H = 0.93 or 0.96 Å and included in the final cycles of refinement using a riding model with Uiso(H) = 1.2 or 1.5Ueq(C). One of the naphthalene rings is disordered over two sets of sites with refined occpancies of 0.535 (4) and (0.465 (4).
Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
![[Figure 1]](./lh5416fig1thm.gif)
| Fig. 1. The molecular structure of one of the independent molecules of (I) showing displacement ellipsoids at the 30% probability [symmetry code (A): -x+2, -y+1, -z+1]. |
![[Figure 2]](./lh5416fig2thm.gif)
| Fig. 2. The molecular structure of the other independent molecule of (I) showing displacement ellipsoids at the 30% probability. [symmetry code (A): -x+1, -y+2, -z]. |
| [Cu2(C12H9O2)4(C3H7NO)2] | Z = 2 |
| Mr = 1014.04 | F(000) = 1052 |
| Triclinic, P1 | Dx = 1.386 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
| a = 10.6704 (7) Å | Cell parameters from 7990 reflections |
| b = 12.3561 (8) Å | θ = 2.2–26.9° |
| c = 20.7734 (14) Å | µ = 0.94 mm−1 |
| α = 74.8390 (11)° | T = 298 K |
| β = 84.898 (1)° | Block, green |
| γ = 66.848 (1)° | 0.10 × 0.10 × 0.10 mm |
| V = 2430.3 (3) Å3 |
| Bruker APEXII CCD diffractometer | 8516 independent reflections |
| Radiation source: fine-focus sealed tube | 7103 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.019 |
| φ and ω scans | θmax = 25.0°, θmin = 2.1° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −12→12 |
| Tmin = 0.945, Tmax = 0.945 | k = −14→14 |
| 18538 measured reflections | l = −24→24 |
| 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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.115 | H-atom parameters constrained |
| S = 1.04 | w = 1/[σ2(Fo2) + (0.0486P)2 + 2.352P] where P = (Fo2 + 2Fc2)/3 |
| 8516 reflections | (Δ/σ)max = 0.001 |
| 630 parameters | Δρmax = 0.61 e Å−3 |
| 16 restraints | Δρmin = −1.25 e Å−3 |
| [Cu2(C12H9O2)4(C3H7NO)2] | γ = 66.848 (1)° |
| Mr = 1014.04 | V = 2430.3 (3) Å3 |
| Triclinic, P1 | Z = 2 |
| a = 10.6704 (7) Å | Mo Kα radiation |
| b = 12.3561 (8) Å | µ = 0.94 mm−1 |
| c = 20.7734 (14) Å | T = 298 K |
| α = 74.8390 (11)° | 0.10 × 0.10 × 0.10 mm |
| β = 84.898 (1)° |
| Bruker APEXII CCD diffractometer | 8516 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 7103 reflections with I > 2σ(I) |
| Tmin = 0.945, Tmax = 0.945 | Rint = 0.019 |
| 18538 measured reflections | θmax = 25.0° |
| R[F2 > 2σ(F2)] = 0.043 | H-atom parameters constrained |
| wR(F2) = 0.115 | Δρmax = 0.61 e Å−3 |
| S = 1.04 | Δρmin = −1.25 e Å−3 |
| 8516 reflections | Absolute structure: ? |
| 630 parameters | Flack parameter: ? |
| 16 restraints | Rogers parameter: ? |
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. |
| x | y | z | Uiso*/Ueq | Occ. (<1) | |
| Cu1 | 0.86554 (3) | 0.53893 (3) | 0.496213 (16) | 0.03371 (10) | |
| O1 | 0.8617 (2) | 0.69486 (17) | 0.50264 (11) | 0.0474 (5) | |
| O2 | 0.8686 (2) | 0.48613 (19) | 0.59443 (10) | 0.0488 (5) | |
| O3 | 1.0954 (2) | 0.4191 (2) | 0.60003 (10) | 0.0505 (5) | |
| O4 | 1.0886 (2) | 0.62875 (17) | 0.50813 (11) | 0.0478 (5) | |
| O5 | 0.65309 (19) | 0.59391 (19) | 0.47337 (11) | 0.0481 (5) | |
| N1 | 0.5038 (2) | 0.5742 (2) | 0.41095 (13) | 0.0501 (6) | |
| C1 | 0.9708 (3) | 0.7076 (2) | 0.50813 (14) | 0.0396 (6) | |
| C2 | 0.9582 (3) | 0.8313 (3) | 0.51355 (18) | 0.0518 (8) | |
| H2A | 0.9535 | 0.8829 | 0.4690 | 0.062* | |
| H2B | 0.8734 | 0.8676 | 0.5355 | 0.062* | |
| C3 | 1.0737 (3) | 0.8278 (3) | 0.55139 (17) | 0.0491 (7) | |
| C4 | 1.1703 (3) | 0.8671 (3) | 0.51830 (19) | 0.0573 (8) | |
| H4 | 1.1640 | 0.8955 | 0.4721 | 0.069* | |
| C5 | 1.2789 (4) | 0.8656 (3) | 0.5526 (2) | 0.0696 (10) | |
| H5 | 1.3437 | 0.8925 | 0.5290 | 0.083* | |
| C6 | 1.2896 (4) | 0.8254 (4) | 0.6193 (2) | 0.0724 (11) | |
| H6 | 1.3610 | 0.8263 | 0.6414 | 0.087* | |
| C7 | 1.1946 (4) | 0.7819 (3) | 0.6562 (2) | 0.0652 (9) | |
| C8 | 1.0849 (3) | 0.7827 (3) | 0.62141 (19) | 0.0558 (8) | |
| C9 | 0.9902 (4) | 0.7392 (4) | 0.6595 (2) | 0.0755 (11) | |
| H9 | 0.9184 | 0.7383 | 0.6375 | 0.091* | |
| C10 | 1.0003 (6) | 0.6988 (5) | 0.7266 (3) | 0.1008 (15) | |
| H10 | 0.9356 | 0.6716 | 0.7502 | 0.121* | |
| C11 | 1.1078 (7) | 0.6980 (5) | 0.7602 (3) | 0.1063 (17) | |
| H11 | 1.1148 | 0.6701 | 0.8064 | 0.128* | |
| C12 | 1.2028 (5) | 0.7377 (5) | 0.7261 (3) | 0.0910 (14) | |
| H12 | 1.2746 | 0.7356 | 0.7494 | 0.109* | |
| C13 | 0.9805 (3) | 0.4372 (3) | 0.62552 (14) | 0.0429 (7) | |
| C14 | 0.9800 (4) | 0.3984 (4) | 0.70118 (16) | 0.0592 (9) | |
| H14E | 1.0662 | 0.3317 | 0.7160 | 0.071* | |
| H14F | 0.9765 | 0.4655 | 0.7182 | 0.071* | |
| C15 | 0.8679 (3) | 0.3594 (3) | 0.73282 (15) | 0.0514 (8) | |
| C16 | 0.7770 (5) | 0.4238 (4) | 0.77268 (18) | 0.0784 (12) | |
| H16A | 0.7809 | 0.4954 | 0.7772 | 0.094* | |
| C17 | 0.6777 (5) | 0.3840 (6) | 0.8070 (2) | 0.111 (2) | |
| H17A | 0.6164 | 0.4294 | 0.8339 | 0.133* | |
| C18 | 0.6706 (5) | 0.2804 (6) | 0.8014 (3) | 0.106 (2) | |
| H18A | 0.6056 | 0.2541 | 0.8253 | 0.127* | |
| C19 | 0.7591 (4) | 0.2122 (4) | 0.7603 (2) | 0.0781 (13) | |
| C20 | 0.8604 (3) | 0.2511 (3) | 0.72557 (16) | 0.0559 (8) | |
| C21 | 0.9501 (4) | 0.1789 (3) | 0.6852 (2) | 0.0743 (11) | |
| H21A | 1.0179 | 0.2020 | 0.6620 | 0.089* | |
| C22 | 0.9383 (7) | 0.0752 (4) | 0.6798 (3) | 0.115 (2) | |
| H22A | 0.9979 | 0.0288 | 0.6529 | 0.138* | |
| C23 | 0.8379 (10) | 0.0380 (6) | 0.7143 (4) | 0.146 (3) | |
| H23A | 0.8312 | −0.0328 | 0.7103 | 0.176* | |
| C24 | 0.7526 (7) | 0.1037 (6) | 0.7525 (4) | 0.119 (2) | |
| H24A | 0.6861 | 0.0780 | 0.7750 | 0.143* | |
| C25 | 0.6245 (3) | 0.5422 (3) | 0.43674 (16) | 0.0478 (7) | |
| H25A | 0.6915 | 0.4723 | 0.4233 | 0.057* | |
| C26 | 0.3898 (3) | 0.6778 (3) | 0.4237 (2) | 0.0679 (10) | |
| H26A | 0.4112 | 0.7001 | 0.4610 | 0.102* | |
| H26B | 0.3109 | 0.6574 | 0.4336 | 0.102* | |
| H26C | 0.3712 | 0.7447 | 0.3850 | 0.102* | |
| C27 | 0.4771 (4) | 0.5066 (4) | 0.3696 (2) | 0.0817 (12) | |
| H27A | 0.5601 | 0.4409 | 0.3641 | 0.122* | |
| H27B | 0.4427 | 0.5597 | 0.3267 | 0.122* | |
| H27C | 0.4108 | 0.4747 | 0.3908 | 0.122* | |
| Cu2 | 0.38926 (5) | 0.97711 (5) | 0.01857 (2) | 0.07018 (17) | |
| O6 | 0.3889 (3) | 1.0570 (3) | 0.08925 (12) | 0.0702 (7) | |
| O7 | 0.5200 (3) | 0.8234 (3) | 0.07183 (12) | 0.0721 (7) | |
| O8 | 0.5772 (3) | 1.0939 (3) | 0.05852 (13) | 0.0949 (11) | |
| O9 | 0.7071 (3) | 0.8613 (3) | 0.04101 (13) | 0.0897 (10) | |
| O10 | 0.2111 (3) | 0.9402 (3) | 0.05243 (13) | 0.0763 (8) | |
| N2 | 0.0108 (3) | 0.9822 (3) | 0.10633 (17) | 0.0696 (8) | |
| C28 | 0.4779 (4) | 1.0960 (4) | 0.09576 (17) | 0.0685 (10) | |
| C29 | 0.4625 (5) | 1.1507 (4) | 0.15480 (17) | 0.0715 (10) | |
| H2B1 | 0.3675 | 1.2023 | 0.1582 | 0.086* | |
| H2B2 | 0.5151 | 1.2014 | 0.1471 | 0.086* | |
| C30 | 0.5091 (3) | 1.0557 (3) | 0.22023 (16) | 0.0516 (8) | |
| C31 | 0.5883 (4) | 0.9376 (4) | 0.22208 (19) | 0.0686 (10) | |
| H4B | 0.6157 | 0.9151 | 0.1821 | 0.082* | |
| C32 | 0.6299 (4) | 0.8485 (4) | 0.2826 (2) | 0.0802 (12) | |
| H5B | 0.6840 | 0.7684 | 0.2823 | 0.096* | |
| C33 | 0.5912 (4) | 0.8797 (4) | 0.3410 (2) | 0.0753 (11) | |
| H6B | 0.6193 | 0.8205 | 0.3808 | 0.090* | |
| C34 | 0.5097 (4) | 0.9990 (3) | 0.34265 (16) | 0.0574 (8) | |
| C35 | 0.4690 (3) | 1.0902 (3) | 0.28141 (15) | 0.0490 (7) | |
| C36 | 0.3910 (4) | 1.2112 (4) | 0.2850 (2) | 0.0646 (9) | |
| H9B | 0.3647 | 1.2723 | 0.2457 | 0.078* | |
| C37 | 0.3538 (4) | 1.2402 (5) | 0.3447 (2) | 0.0842 (13) | |
| H10B | 0.3037 | 1.3207 | 0.3456 | 0.101* | |
| C38 | 0.3899 (4) | 1.1507 (6) | 0.4042 (2) | 0.0883 (15) | |
| H11B | 0.3622 | 1.1711 | 0.4447 | 0.106* | |
| C39 | 0.4654 (4) | 1.0341 (5) | 0.40307 (19) | 0.0784 (12) | |
| H12B | 0.4889 | 0.9751 | 0.4432 | 0.094* | |
| C40 | 0.6459 (4) | 0.7965 (4) | 0.07327 (17) | 0.0671 (10) | |
| C41 | 0.7311 (4) | 0.6765 (4) | 0.1201 (2) | 0.0778 (10) | |
| H14A | 0.6651 | 0.6458 | 0.1444 | 0.093* | 0.535 (4) |
| H14B | 0.7704 | 0.6991 | 0.1523 | 0.093* | 0.535 (4) |
| H14C | 0.6961 | 0.6687 | 0.1651 | 0.093* | 0.465 (4) |
| H14D | 0.7984 | 0.7121 | 0.1174 | 0.093* | 0.465 (4) |
| C42 | 0.8463 (8) | 0.5647 (7) | 0.1048 (4) | 0.0778 (10) | 0.535 (4) |
| C43 | 0.9800 (8) | 0.5434 (7) | 0.1138 (4) | 0.072 (2) | 0.535 (4) |
| H16B | 1.0023 | 0.5938 | 0.1329 | 0.087* | 0.535 (4) |
| C44 | 1.0858 (10) | 0.4438 (8) | 0.0940 (6) | 0.082 (3) | 0.535 (4) |
| H44 | 1.1765 | 0.4304 | 0.1001 | 0.098* | 0.535 (4) |
| C45 | 1.0560 (10) | 0.3701 (9) | 0.0672 (4) | 0.081 (3) | 0.535 (4) |
| H18B | 1.1263 | 0.3054 | 0.0551 | 0.097* | 0.535 (4) |
| C46 | 0.9203 (9) | 0.3882 (7) | 0.0568 (4) | 0.078 (2) | 0.535 (4) |
| C47 | 0.8127 (8) | 0.4873 (6) | 0.0759 (3) | 0.0697 (19) | 0.535 (4) |
| C48 | 0.6745 (12) | 0.5034 (9) | 0.0661 (6) | 0.1086 (19) | 0.535 (4) |
| H21B | 0.6032 | 0.5714 | 0.0745 | 0.130* | 0.535 (4) |
| C49 | 0.6473 (13) | 0.4207 (10) | 0.0449 (7) | 0.1086 (19) | 0.535 (4) |
| H22B | 0.5592 | 0.4220 | 0.0470 | 0.130* | 0.535 (4) |
| C50 | 0.7563 (11) | 0.3300 (9) | 0.0188 (5) | 0.1086 (19) | 0.535 (4) |
| H23B | 0.7362 | 0.2840 | −0.0047 | 0.130* | 0.535 (4) |
| C51 | 0.8885 (11) | 0.3115 (9) | 0.0284 (5) | 0.1086 (19) | 0.535 (4) |
| H24B | 0.9583 | 0.2470 | 0.0158 | 0.130* | 0.535 (4) |
| C42' | 0.7119 (12) | 0.5882 (10) | 0.0827 (6) | 0.1024 (14) | 0.465 (4) |
| C43' | 0.6485 (11) | 0.5158 (10) | 0.1209 (7) | 0.1024 (14) | 0.465 (4) |
| H16' | 0.6118 | 0.5279 | 0.1620 | 0.123* | 0.465 (4) |
| C44' | 0.6408 (11) | 0.4208 (10) | 0.0953 (6) | 0.1024 (14) | 0.465 (4) |
| H17' | 0.6018 | 0.3688 | 0.1212 | 0.123* | 0.465 (4) |
| C45' | 0.6911 (13) | 0.4048 (14) | 0.0316 (7) | 0.1024 (14) | 0.465 (4) |
| H18' | 0.6783 | 0.3475 | 0.0144 | 0.123* | 0.465 (4) |
| C46' | 0.7591 (11) | 0.4747 (10) | −0.0045 (6) | 0.1024 (14) | 0.465 (4) |
| C47' | 0.7665 (11) | 0.5695 (10) | 0.0209 (6) | 0.1024 (14) | 0.465 (4) |
| C48' | 0.8347 (11) | 0.6422 (10) | −0.0192 (6) | 0.1024 (14) | 0.465 (4) |
| H21' | 0.8411 | 0.7054 | −0.0051 | 0.123* | 0.465 (4) |
| C49' | 0.8908 (14) | 0.6185 (14) | −0.0786 (7) | 0.1024 (14) | 0.465 (4) |
| H22' | 0.9348 | 0.6661 | −0.1046 | 0.123* | 0.465 (4) |
| C50' | 0.8824 (14) | 0.5247 (13) | −0.1000 (8) | 0.1024 (14) | 0.465 (4) |
| H23' | 0.9236 | 0.5085 | −0.1397 | 0.123* | 0.465 (4) |
| C51' | 0.8184 (11) | 0.4587 (10) | −0.0659 (6) | 0.1024 (14) | 0.465 (4) |
| H24' | 0.8118 | 0.3986 | −0.0829 | 0.123* | 0.465 (4) |
| C52 | 0.1214 (4) | 1.0013 (4) | 0.0845 (2) | 0.0746 (12) | |
| H25B | 0.1181 | 1.0735 | 0.0955 | 0.090* | |
| C53 | −0.0098 (5) | 0.8796 (5) | 0.0961 (2) | 0.0886 (14) | |
| H26D | 0.0601 | 0.8406 | 0.0678 | 0.133* | |
| H26E | −0.0974 | 0.9067 | 0.0753 | 0.133* | |
| H26F | −0.0059 | 0.8230 | 0.1382 | 0.133* | |
| C54 | −0.0924 (5) | 1.0569 (6) | 0.1441 (4) | 0.143 (3) | |
| H27D | −0.0628 | 1.1158 | 0.1530 | 0.215* | |
| H27E | −0.1064 | 1.0064 | 0.1856 | 0.215* | |
| H27F | −0.1763 | 1.0981 | 0.1189 | 0.215* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Cu1 | 0.02974 (17) | 0.03313 (17) | 0.04065 (19) | −0.01368 (13) | −0.00106 (13) | −0.01000 (13) |
| O1 | 0.0385 (11) | 0.0370 (10) | 0.0708 (14) | −0.0141 (9) | −0.0009 (10) | −0.0200 (10) |
| O2 | 0.0444 (12) | 0.0598 (13) | 0.0414 (11) | −0.0218 (10) | 0.0018 (9) | −0.0085 (10) |
| O3 | 0.0453 (12) | 0.0674 (14) | 0.0395 (11) | −0.0258 (11) | 0.0002 (9) | −0.0074 (10) |
| O4 | 0.0395 (11) | 0.0347 (10) | 0.0728 (15) | −0.0128 (9) | −0.0053 (10) | −0.0195 (10) |
| O5 | 0.0326 (10) | 0.0517 (12) | 0.0615 (13) | −0.0155 (9) | −0.0056 (9) | −0.0155 (10) |
| N1 | 0.0376 (13) | 0.0526 (15) | 0.0572 (16) | −0.0145 (12) | −0.0109 (12) | −0.0098 (12) |
| C1 | 0.0411 (16) | 0.0341 (14) | 0.0448 (16) | −0.0141 (12) | −0.0023 (12) | −0.0113 (12) |
| C2 | 0.0467 (17) | 0.0347 (15) | 0.077 (2) | −0.0139 (13) | −0.0058 (16) | −0.0184 (15) |
| C3 | 0.0483 (17) | 0.0318 (14) | 0.071 (2) | −0.0140 (13) | −0.0024 (15) | −0.0193 (14) |
| C4 | 0.058 (2) | 0.0420 (17) | 0.076 (2) | −0.0208 (15) | −0.0008 (17) | −0.0174 (16) |
| C5 | 0.055 (2) | 0.066 (2) | 0.098 (3) | −0.0314 (18) | 0.002 (2) | −0.024 (2) |
| C6 | 0.052 (2) | 0.072 (2) | 0.102 (3) | −0.0239 (19) | −0.015 (2) | −0.030 (2) |
| C7 | 0.062 (2) | 0.059 (2) | 0.076 (3) | −0.0163 (18) | −0.0079 (19) | −0.0277 (19) |
| C8 | 0.0523 (19) | 0.0468 (17) | 0.076 (2) | −0.0185 (15) | 0.0017 (17) | −0.0286 (17) |
| C9 | 0.084 (3) | 0.086 (3) | 0.074 (3) | −0.046 (2) | 0.009 (2) | −0.029 (2) |
| C10 | 0.122 (4) | 0.119 (4) | 0.086 (3) | −0.071 (4) | 0.018 (3) | −0.031 (3) |
| C11 | 0.134 (5) | 0.117 (4) | 0.069 (3) | −0.052 (4) | 0.002 (3) | −0.020 (3) |
| C12 | 0.091 (3) | 0.097 (3) | 0.089 (3) | −0.030 (3) | −0.020 (3) | −0.032 (3) |
| C13 | 0.0501 (18) | 0.0445 (16) | 0.0413 (16) | −0.0262 (14) | 0.0009 (14) | −0.0101 (13) |
| C14 | 0.067 (2) | 0.079 (2) | 0.0399 (17) | −0.0407 (19) | −0.0023 (15) | −0.0066 (16) |
| C15 | 0.0529 (18) | 0.0597 (19) | 0.0338 (15) | −0.0212 (16) | −0.0022 (14) | 0.0013 (14) |
| C16 | 0.091 (3) | 0.087 (3) | 0.043 (2) | −0.025 (2) | 0.011 (2) | −0.0122 (19) |
| C17 | 0.083 (3) | 0.146 (5) | 0.060 (3) | −0.016 (4) | 0.029 (2) | −0.008 (3) |
| C18 | 0.063 (3) | 0.149 (5) | 0.072 (3) | −0.046 (3) | 0.004 (2) | 0.036 (3) |
| C19 | 0.063 (2) | 0.090 (3) | 0.066 (2) | −0.042 (2) | −0.020 (2) | 0.031 (2) |
| C20 | 0.0502 (19) | 0.058 (2) | 0.0472 (18) | −0.0207 (16) | −0.0111 (15) | 0.0117 (15) |
| C21 | 0.082 (3) | 0.052 (2) | 0.075 (3) | −0.018 (2) | −0.008 (2) | −0.0012 (19) |
| C22 | 0.157 (6) | 0.056 (3) | 0.116 (4) | −0.025 (3) | −0.029 (4) | −0.010 (3) |
| C23 | 0.212 (9) | 0.073 (4) | 0.160 (7) | −0.081 (5) | −0.068 (6) | 0.027 (4) |
| C24 | 0.120 (5) | 0.106 (5) | 0.129 (5) | −0.080 (4) | −0.053 (4) | 0.049 (4) |
| C25 | 0.0348 (15) | 0.0483 (17) | 0.0558 (19) | −0.0123 (13) | −0.0044 (14) | −0.0098 (14) |
| C26 | 0.0378 (18) | 0.063 (2) | 0.091 (3) | −0.0095 (16) | −0.0100 (17) | −0.012 (2) |
| C27 | 0.069 (3) | 0.094 (3) | 0.089 (3) | −0.027 (2) | −0.022 (2) | −0.035 (2) |
| Cu2 | 0.0715 (3) | 0.1253 (4) | 0.0355 (2) | −0.0693 (3) | 0.00152 (19) | −0.0063 (2) |
| O6 | 0.0740 (17) | 0.105 (2) | 0.0453 (13) | −0.0516 (16) | −0.0009 (12) | −0.0139 (13) |
| O7 | 0.0636 (16) | 0.099 (2) | 0.0579 (15) | −0.0423 (15) | 0.0122 (12) | −0.0134 (14) |
| O8 | 0.113 (2) | 0.173 (3) | 0.0461 (15) | −0.106 (2) | 0.0112 (15) | −0.0278 (17) |
| O9 | 0.0752 (18) | 0.150 (3) | 0.0545 (15) | −0.072 (2) | −0.0109 (13) | 0.0065 (17) |
| O10 | 0.0654 (17) | 0.114 (2) | 0.0606 (16) | −0.0584 (17) | 0.0033 (13) | −0.0037 (15) |
| N2 | 0.0477 (17) | 0.074 (2) | 0.081 (2) | −0.0245 (15) | −0.0078 (15) | −0.0046 (17) |
| C28 | 0.087 (3) | 0.094 (3) | 0.0348 (18) | −0.053 (2) | −0.0097 (18) | −0.0002 (17) |
| C29 | 0.095 (3) | 0.078 (3) | 0.046 (2) | −0.041 (2) | −0.0122 (19) | −0.0057 (18) |
| C30 | 0.0500 (18) | 0.063 (2) | 0.0435 (17) | −0.0241 (16) | −0.0039 (14) | −0.0108 (15) |
| C31 | 0.065 (2) | 0.077 (3) | 0.059 (2) | −0.015 (2) | −0.0025 (18) | −0.028 (2) |
| C32 | 0.079 (3) | 0.060 (2) | 0.085 (3) | −0.006 (2) | −0.021 (2) | −0.016 (2) |
| C33 | 0.085 (3) | 0.072 (3) | 0.060 (2) | −0.030 (2) | −0.018 (2) | 0.006 (2) |
| C34 | 0.055 (2) | 0.078 (2) | 0.0443 (18) | −0.0350 (18) | −0.0006 (15) | −0.0084 (16) |
| C35 | 0.0386 (16) | 0.065 (2) | 0.0467 (17) | −0.0228 (15) | −0.0004 (13) | −0.0152 (15) |
| C36 | 0.051 (2) | 0.076 (2) | 0.067 (2) | −0.0173 (18) | −0.0099 (17) | −0.0249 (19) |
| C37 | 0.048 (2) | 0.110 (3) | 0.100 (4) | −0.012 (2) | −0.004 (2) | −0.060 (3) |
| C38 | 0.055 (2) | 0.152 (5) | 0.070 (3) | −0.038 (3) | 0.014 (2) | −0.055 (3) |
| C39 | 0.075 (3) | 0.127 (4) | 0.046 (2) | −0.057 (3) | 0.0077 (19) | −0.017 (2) |
| C40 | 0.076 (3) | 0.100 (3) | 0.0392 (18) | −0.044 (2) | 0.0075 (17) | −0.0273 (19) |
| C41 | 0.072 (2) | 0.073 (2) | 0.086 (3) | −0.0228 (19) | 0.0066 (19) | −0.026 (2) |
| C42 | 0.072 (2) | 0.073 (2) | 0.086 (3) | −0.0228 (19) | 0.0066 (19) | −0.026 (2) |
| C43 | 0.074 (5) | 0.071 (5) | 0.060 (4) | −0.022 (4) | −0.007 (4) | −0.001 (3) |
| C44 | 0.075 (6) | 0.053 (5) | 0.111 (7) | −0.021 (4) | −0.006 (5) | −0.013 (5) |
| C45 | 0.080 (7) | 0.073 (5) | 0.061 (5) | −0.005 (5) | 0.015 (5) | −0.013 (4) |
| C46 | 0.110 (7) | 0.056 (4) | 0.051 (4) | −0.018 (4) | −0.006 (4) | −0.004 (3) |
| C47 | 0.081 (5) | 0.056 (4) | 0.054 (4) | −0.013 (4) | 0.000 (4) | −0.007 (3) |
| C48 | 0.132 (5) | 0.081 (3) | 0.117 (4) | −0.036 (3) | −0.021 (4) | −0.030 (3) |
| C49 | 0.132 (5) | 0.081 (3) | 0.117 (4) | −0.036 (3) | −0.021 (4) | −0.030 (3) |
| C50 | 0.132 (5) | 0.081 (3) | 0.117 (4) | −0.036 (3) | −0.021 (4) | −0.030 (3) |
| C51 | 0.132 (5) | 0.081 (3) | 0.117 (4) | −0.036 (3) | −0.021 (4) | −0.030 (3) |
| C42' | 0.090 (3) | 0.082 (3) | 0.114 (3) | −0.0068 (19) | −0.019 (2) | −0.024 (2) |
| C43' | 0.090 (3) | 0.082 (3) | 0.114 (3) | −0.0068 (19) | −0.019 (2) | −0.024 (2) |
| C44' | 0.090 (3) | 0.082 (3) | 0.114 (3) | −0.0068 (19) | −0.019 (2) | −0.024 (2) |
| C45' | 0.090 (3) | 0.082 (3) | 0.114 (3) | −0.0068 (19) | −0.019 (2) | −0.024 (2) |
| C46' | 0.090 (3) | 0.082 (3) | 0.114 (3) | −0.0068 (19) | −0.019 (2) | −0.024 (2) |
| C47' | 0.090 (3) | 0.082 (3) | 0.114 (3) | −0.0068 (19) | −0.019 (2) | −0.024 (2) |
| C48' | 0.090 (3) | 0.082 (3) | 0.114 (3) | −0.0068 (19) | −0.019 (2) | −0.024 (2) |
| C49' | 0.090 (3) | 0.082 (3) | 0.114 (3) | −0.0068 (19) | −0.019 (2) | −0.024 (2) |
| C50' | 0.090 (3) | 0.082 (3) | 0.114 (3) | −0.0068 (19) | −0.019 (2) | −0.024 (2) |
| C51' | 0.090 (3) | 0.082 (3) | 0.114 (3) | −0.0068 (19) | −0.019 (2) | −0.024 (2) |
| C52 | 0.059 (2) | 0.066 (2) | 0.091 (3) | −0.032 (2) | −0.019 (2) | 0.011 (2) |
| C53 | 0.083 (3) | 0.123 (4) | 0.080 (3) | −0.069 (3) | −0.002 (2) | −0.011 (3) |
| C54 | 0.068 (3) | 0.132 (5) | 0.221 (8) | −0.018 (3) | 0.027 (4) | −0.071 (5) |
| Cu1—O1 | 1.9501 (19) | O9—Cu2ii | 1.974 (3) |
| Cu1—O4i | 1.9578 (18) | O10—C52 | 1.230 (5) |
| Cu1—O2 | 1.972 (2) | N2—C52 | 1.312 (5) |
| Cu1—O3i | 1.980 (2) | N2—C53 | 1.439 (5) |
| Cu1—O5 | 2.1535 (19) | N2—C54 | 1.452 (6) |
| Cu1—Cu1i | 2.6485 (6) | C28—C29 | 1.516 (5) |
| O1—C1 | 1.253 (3) | C29—C30 | 1.516 (5) |
| O2—C13 | 1.254 (4) | C29—H2B1 | 0.9700 |
| O3—C13 | 1.251 (4) | C29—H2B2 | 0.9700 |
| O3—Cu1i | 1.980 (2) | C30—C31 | 1.361 (5) |
| O4—C1 | 1.251 (3) | C30—C35 | 1.422 (4) |
| O4—Cu1i | 1.9578 (18) | C31—C32 | 1.407 (6) |
| O5—C25 | 1.236 (4) | C31—H4B | 0.9300 |
| N1—C25 | 1.309 (4) | C32—C33 | 1.349 (6) |
| N1—C26 | 1.444 (4) | C32—H5B | 0.9300 |
| N1—C27 | 1.457 (4) | C33—C34 | 1.395 (5) |
| C1—C2 | 1.514 (4) | C33—H6B | 0.9300 |
| C2—C3 | 1.501 (4) | C34—C39 | 1.416 (5) |
| C2—H2A | 0.9700 | C34—C35 | 1.428 (5) |
| C2—H2B | 0.9700 | C35—C36 | 1.415 (5) |
| C3—C4 | 1.365 (5) | C36—C37 | 1.362 (5) |
| C3—C8 | 1.413 (5) | C36—H9B | 0.9300 |
| C4—C5 | 1.405 (5) | C37—C38 | 1.391 (7) |
| C4—H4 | 0.9300 | C37—H10B | 0.9300 |
| C5—C6 | 1.343 (6) | C38—C39 | 1.352 (7) |
| C5—H5 | 0.9300 | C38—H11B | 0.9300 |
| C6—C7 | 1.407 (6) | C39—H12B | 0.9300 |
| C6—H6 | 0.9300 | C40—C41 | 1.521 (6) |
| C7—C12 | 1.409 (6) | C41—C42 | 1.532 (8) |
| C7—C8 | 1.424 (5) | C41—C42' | 1.575 (12) |
| C8—C9 | 1.414 (5) | C41—H14A | 0.9700 |
| C9—C10 | 1.351 (6) | C41—H14B | 0.9700 |
| C9—H9 | 0.9300 | C41—H14C | 0.9700 |
| C10—C11 | 1.390 (7) | C41—H14D | 0.9700 |
| C10—H10 | 0.9300 | C42—C43 | 1.365 (11) |
| C11—C12 | 1.361 (7) | C42—C47 | 1.418 (10) |
| C11—H11 | 0.9300 | C43—C44 | 1.431 (13) |
| C12—H12 | 0.9300 | C43—H16B | 0.9300 |
| C13—C14 | 1.519 (4) | C44—C45 | 1.329 (13) |
| C14—C15 | 1.498 (4) | C44—H44 | 0.9300 |
| C14—H14E | 0.9700 | C45—C46 | 1.403 (11) |
| C14—H14F | 0.9700 | C45—H18B | 0.9300 |
| C15—C16 | 1.361 (5) | C46—C51 | 1.394 (12) |
| C15—C20 | 1.419 (5) | C46—C47 | 1.429 (10) |
| C16—C17 | 1.402 (7) | C47—C48 | 1.434 (13) |
| C16—H16A | 0.9300 | C48—C49 | 1.348 (15) |
| C17—C18 | 1.347 (8) | C48—H21B | 0.9300 |
| C17—H17A | 0.9300 | C49—C50 | 1.444 (12) |
| C18—C19 | 1.393 (7) | C49—H22B | 0.9300 |
| C18—H18A | 0.9300 | C50—C51 | 1.361 (12) |
| C19—C20 | 1.417 (5) | C50—H23B | 0.9300 |
| C19—C24 | 1.420 (8) | C51—H24B | 0.9300 |
| C20—C21 | 1.412 (5) | C42'—C43' | 1.377 (16) |
| C21—C22 | 1.369 (6) | C42'—C47' | 1.399 (16) |
| C21—H21A | 0.9300 | C43'—C44' | 1.442 (16) |
| C22—C23 | 1.396 (10) | C43'—H16' | 0.9300 |
| C22—H22A | 0.9300 | C44'—C45' | 1.416 (14) |
| C23—C24 | 1.321 (10) | C44'—H17' | 0.9300 |
| C23—H23A | 0.9300 | C45'—C46' | 1.375 (18) |
| C24—H24A | 0.9300 | C45'—H18' | 0.9300 |
| C25—H25A | 0.9695 | C46'—C51' | 1.399 (13) |
| C26—H26A | 0.9600 | C46'—C47' | 1.437 (15) |
| C26—H26B | 0.9600 | C47'—C48' | 1.430 (13) |
| C26—H26C | 0.9600 | C48'—C49' | 1.373 (14) |
| C27—H27A | 0.9600 | C48'—H21' | 0.9300 |
| C27—H27B | 0.9600 | C49'—C50' | 1.380 (15) |
| C27—H27C | 0.9600 | C49'—H22' | 0.9300 |
| Cu2—O8ii | 1.962 (3) | C50'—C51' | 1.297 (14) |
| Cu2—O7 | 1.967 (3) | C50'—H23' | 0.9300 |
| Cu2—O6 | 1.970 (3) | C51'—H24' | 0.9300 |
| Cu2—O9ii | 1.974 (3) | C52—H25B | 0.9636 |
| Cu2—O10 | 2.143 (2) | C53—H26D | 0.9600 |
| Cu2—Cu2ii | 2.6455 (8) | C53—H26E | 0.9600 |
| O6—C28 | 1.254 (4) | C53—H26F | 0.9600 |
| O7—C40 | 1.252 (5) | C54—H27D | 0.9600 |
| O8—C28 | 1.251 (5) | C54—H27E | 0.9600 |
| O8—Cu2ii | 1.962 (3) | C54—H27F | 0.9600 |
| O9—C40 | 1.253 (5) | ||
| O1—Cu1—O4i | 167.77 (8) | O8—C28—O6 | 126.3 (4) |
| O1—Cu1—O2 | 89.29 (9) | O8—C28—C29 | 117.5 (3) |
| O4i—Cu1—O2 | 89.56 (9) | O6—C28—C29 | 116.1 (4) |
| O1—Cu1—O3i | 89.33 (9) | C28—C29—C30 | 113.0 (3) |
| O4i—Cu1—O3i | 89.23 (9) | C28—C29—H2B1 | 109.0 |
| O2—Cu1—O3i | 167.86 (8) | C30—C29—H2B1 | 109.0 |
| O1—Cu1—O5 | 98.64 (8) | C28—C29—H2B2 | 109.0 |
| O4i—Cu1—O5 | 93.52 (8) | C30—C29—H2B2 | 109.0 |
| O2—Cu1—O5 | 101.74 (8) | H2B1—C29—H2B2 | 107.8 |
| O3i—Cu1—O5 | 90.39 (8) | C31—C30—C35 | 118.9 (3) |
| O1—Cu1—Cu1i | 86.47 (6) | C31—C30—C29 | 121.7 (3) |
| O4i—Cu1—Cu1i | 81.31 (6) | C35—C30—C29 | 119.5 (3) |
| O2—Cu1—Cu1i | 86.99 (6) | C30—C31—C32 | 122.0 (4) |
| O3i—Cu1—Cu1i | 80.89 (6) | C30—C31—H4B | 119.0 |
| O5—Cu1—Cu1i | 169.88 (6) | C32—C31—H4B | 119.0 |
| C1—O1—Cu1 | 120.12 (17) | C33—C32—C31 | 119.7 (4) |
| C13—O2—Cu1 | 119.63 (19) | C33—C32—H5B | 120.1 |
| C13—O3—Cu1i | 126.54 (19) | C31—C32—H5B | 120.1 |
| C1—O4—Cu1i | 125.86 (18) | C32—C33—C34 | 121.2 (4) |
| C25—O5—Cu1 | 117.18 (19) | C32—C33—H6B | 119.4 |
| C25—N1—C26 | 120.9 (3) | C34—C33—H6B | 119.4 |
| C25—N1—C27 | 122.2 (3) | C33—C34—C39 | 122.5 (4) |
| C26—N1—C27 | 116.9 (3) | C33—C34—C35 | 119.3 (3) |
| O4—C1—O1 | 126.2 (2) | C39—C34—C35 | 118.2 (4) |
| O4—C1—C2 | 117.2 (2) | C36—C35—C30 | 123.3 (3) |
| O1—C1—C2 | 116.5 (2) | C36—C35—C34 | 117.8 (3) |
| C3—C2—C1 | 113.8 (2) | C30—C35—C34 | 118.9 (3) |
| C3—C2—H2A | 108.8 | C37—C36—C35 | 121.4 (4) |
| C1—C2—H2A | 108.8 | C37—C36—H9B | 119.3 |
| C3—C2—H2B | 108.8 | C35—C36—H9B | 119.3 |
| C1—C2—H2B | 108.8 | C36—C37—C38 | 120.7 (4) |
| H2A—C2—H2B | 107.7 | C36—C37—H10B | 119.6 |
| C4—C3—C8 | 119.2 (3) | C38—C37—H10B | 119.6 |
| C4—C3—C2 | 120.2 (3) | C39—C38—C37 | 119.8 (4) |
| C8—C3—C2 | 120.6 (3) | C39—C38—H11B | 120.1 |
| C3—C4—C5 | 121.3 (4) | C37—C38—H11B | 120.1 |
| C3—C4—H4 | 119.3 | C38—C39—C34 | 122.0 (4) |
| C5—C4—H4 | 119.3 | C38—C39—H12B | 119.0 |
| C6—C5—C4 | 120.4 (4) | C34—C39—H12B | 119.0 |
| C6—C5—H5 | 119.8 | O7—C40—O9 | 125.7 (4) |
| C4—C5—H5 | 119.8 | O7—C40—C41 | 117.0 (4) |
| C5—C6—C7 | 121.0 (3) | O9—C40—C41 | 117.3 (4) |
| C5—C6—H6 | 119.5 | C40—C41—C42 | 130.0 (5) |
| C7—C6—H6 | 119.5 | C40—C41—C42' | 98.4 (5) |
| C6—C7—C12 | 122.9 (4) | C42—C41—C42' | 55.2 (5) |
| C6—C7—C8 | 118.6 (4) | C40—C41—H14A | 104.8 |
| C12—C7—C8 | 118.4 (4) | C42—C41—H14A | 104.8 |
| C3—C8—C9 | 122.8 (3) | C42'—C41—H14A | 72.1 |
| C3—C8—C7 | 119.4 (3) | C40—C41—H14B | 104.8 |
| C9—C8—C7 | 117.7 (4) | C42—C41—H14B | 104.8 |
| C10—C9—C8 | 122.3 (4) | C42'—C41—H14B | 156.4 |
| C10—C9—H9 | 118.9 | H14A—C41—H14B | 105.8 |
| C8—C9—H9 | 118.9 | C40—C41—H14C | 112.0 |
| C9—C10—C11 | 119.7 (5) | C42—C41—H14C | 117.4 |
| C9—C10—H10 | 120.1 | C42'—C41—H14C | 113.7 |
| C11—C10—H10 | 120.1 | H14A—C41—H14C | 44.3 |
| C12—C11—C10 | 120.6 (5) | H14B—C41—H14C | 61.5 |
| C12—C11—H11 | 119.7 | C40—C41—H14D | 85.2 |
| C10—C11—H11 | 119.7 | C42—C41—H14D | 87.2 |
| C11—C12—C7 | 121.3 (4) | C42'—C41—H14D | 133.4 |
| C11—C12—H12 | 119.4 | H14A—C41—H14D | 151.9 |
| C7—C12—H12 | 119.4 | H14B—C41—H14D | 46.2 |
| O3—C13—O2 | 125.9 (3) | H14C—C41—H14D | 107.5 |
| O3—C13—C14 | 115.4 (3) | C43—C42—C47 | 119.7 (7) |
| O2—C13—C14 | 118.6 (3) | C43—C42—C41 | 121.4 (7) |
| C15—C14—C13 | 117.5 (3) | C47—C42—C41 | 118.7 (7) |
| C15—C14—H14E | 107.9 | C42—C43—C44 | 120.3 (8) |
| C13—C14—H14E | 107.9 | C42—C43—H16B | 119.8 |
| C15—C14—H14F | 107.9 | C44—C43—H16B | 119.8 |
| C13—C14—H14F | 107.9 | C45—C44—C43 | 120.8 (9) |
| H14E—C14—H14F | 107.2 | C45—C44—H44 | 119.6 |
| C16—C15—C20 | 119.2 (3) | C43—C44—H44 | 119.6 |
| C16—C15—C14 | 120.0 (4) | C44—C45—C46 | 121.1 (8) |
| C20—C15—C14 | 120.7 (3) | C44—C45—H18B | 119.4 |
| C15—C16—C17 | 121.0 (5) | C46—C45—H18B | 119.4 |
| C15—C16—H16A | 119.5 | C45—C46—C51 | 121.4 (9) |
| C17—C16—H16A | 119.5 | C45—C46—C47 | 119.2 (8) |
| C18—C17—C16 | 120.5 (5) | C51—C46—C47 | 119.5 (9) |
| C18—C17—H17A | 119.8 | C42—C47—C48 | 122.5 (7) |
| C16—C17—H17A | 119.8 | C42—C47—C46 | 119.0 (8) |
| C17—C18—C19 | 120.9 (4) | C48—C47—C46 | 118.6 (8) |
| C17—C18—H18A | 119.5 | C49—C48—C47 | 120.5 (10) |
| C19—C18—H18A | 119.5 | C49—C48—H21B | 119.8 |
| C18—C19—C20 | 119.1 (4) | C47—C48—H21B | 119.8 |
| C18—C19—C24 | 122.3 (5) | C48—C49—C50 | 119.2 (12) |
| C20—C19—C24 | 118.6 (5) | C48—C49—H22B | 120.4 |
| C21—C20—C19 | 117.8 (4) | C50—C49—H22B | 120.4 |
| C21—C20—C15 | 123.0 (3) | C51—C50—C49 | 120.2 (10) |
| C19—C20—C15 | 119.2 (4) | C51—C50—H23B | 119.9 |
| C22—C21—C20 | 120.6 (5) | C49—C50—H23B | 119.9 |
| C22—C21—H21A | 119.7 | C50—C51—C46 | 120.7 (10) |
| C20—C21—H21A | 119.7 | C50—C51—H24B | 119.6 |
| C21—C22—C23 | 121.0 (6) | C46—C51—H24B | 119.6 |
| C21—C22—H22A | 119.5 | C43'—C42'—C47' | 120.6 (11) |
| C23—C22—H22A | 119.5 | C43'—C42'—C41 | 113.0 (10) |
| C24—C23—C22 | 119.7 (6) | C47'—C42'—C41 | 126.0 (11) |
| C24—C23—H23A | 120.1 | C42'—C43'—C44' | 118.0 (12) |
| C22—C23—H23A | 120.1 | C42'—C43'—H16' | 121.0 |
| C23—C24—C19 | 122.3 (6) | C44'—C43'—H16' | 121.0 |
| C23—C24—H24A | 118.9 | C45'—C44'—C43' | 121.5 (12) |
| C19—C24—H24A | 118.9 | C45'—C44'—H17' | 119.2 |
| O5—C25—N1 | 125.4 (3) | C43'—C44'—H17' | 119.2 |
| O5—C25—H25A | 122.7 | C46'—C45'—C44' | 119.5 (13) |
| N1—C25—H25A | 111.9 | C46'—C45'—H18' | 120.3 |
| N1—C26—H26A | 109.5 | C44'—C45'—H18' | 120.3 |
| N1—C26—H26B | 109.5 | C45'—C46'—C51' | 122.5 (12) |
| H26A—C26—H26B | 109.5 | C45'—C46'—C47' | 118.8 (11) |
| N1—C26—H26C | 109.5 | C51'—C46'—C47' | 118.7 (11) |
| H26A—C26—H26C | 109.5 | C42'—C47'—C48' | 121.6 (11) |
| H26B—C26—H26C | 109.5 | C42'—C47'—C46' | 121.4 (11) |
| N1—C27—H27A | 109.5 | C48'—C47'—C46' | 116.9 (11) |
| N1—C27—H27B | 109.5 | C49'—C48'—C47' | 119.9 (12) |
| H27A—C27—H27B | 109.5 | C49'—C48'—H21' | 120.1 |
| N1—C27—H27C | 109.5 | C47'—C48'—H21' | 120.1 |
| H27A—C27—H27C | 109.5 | C48'—C49'—C50' | 120.7 (14) |
| H27B—C27—H27C | 109.5 | C48'—C49'—H22' | 119.7 |
| O8ii—Cu2—O7 | 89.67 (14) | C50'—C49'—H22' | 119.7 |
| O8ii—Cu2—O6 | 168.00 (11) | C51'—C50'—C49' | 121.4 (16) |
| O7—Cu2—O6 | 89.60 (11) | C51'—C50'—H23' | 119.3 |
| O8ii—Cu2—O9ii | 89.22 (14) | C49'—C50'—H23' | 119.3 |
| O7—Cu2—O9ii | 167.85 (11) | C50'—C51'—C46' | 122.4 (13) |
| O6—Cu2—O9ii | 88.98 (13) | C50'—C51'—H24' | 118.8 |
| O8ii—Cu2—O10 | 96.72 (12) | C46'—C51'—H24' | 118.8 |
| O7—Cu2—O10 | 95.71 (11) | O10—C52—N2 | 125.3 (4) |
| O6—Cu2—O10 | 95.27 (11) | O10—C52—H25B | 125.7 |
| O9ii—Cu2—O10 | 96.44 (11) | N2—C52—H25B | 109.0 |
| O8ii—Cu2—Cu2ii | 85.27 (8) | N2—C53—H26D | 109.5 |
| O7—Cu2—Cu2ii | 83.41 (8) | N2—C53—H26E | 109.5 |
| O6—Cu2—Cu2ii | 82.75 (7) | H26D—C53—H26E | 109.5 |
| O9ii—Cu2—Cu2ii | 84.44 (8) | N2—C53—H26F | 109.5 |
| O10—Cu2—Cu2ii | 177.82 (8) | H26D—C53—H26F | 109.5 |
| C28—O6—Cu2 | 124.0 (3) | H26E—C53—H26F | 109.5 |
| C40—O7—Cu2 | 124.0 (3) | N2—C54—H27D | 109.5 |
| C28—O8—Cu2ii | 121.6 (2) | N2—C54—H27E | 109.5 |
| C40—O9—Cu2ii | 122.4 (3) | H27D—C54—H27E | 109.5 |
| C52—O10—Cu2 | 123.1 (3) | N2—C54—H27F | 109.5 |
| C52—N2—C53 | 120.1 (4) | H27D—C54—H27F | 109.5 |
| C52—N2—C54 | 123.3 (4) | H27E—C54—H27F | 109.5 |
| C53—N2—C54 | 116.5 (4) |
| Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, −y+2, −z. |
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Chen, L.-F., Zhang, J., Song, L.-J., Wang, W.-G. & Ju, Z.-F. (2004). Acta Cryst. E60, m1032–m1034.
Ji, L.-L., Liu, J.-S. & Song, W.-D. (2011). Acta Cryst. E67, m606.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Xia, H.-T., Liu, Y.-F. & Li, S.-A. (2006). Acta Cryst. E62, m2653–m2655.
Yang, Y.-Q., Li, C.-H. L. W. & Kuang, Y.-F. (2008). Chin. J. Struct. Chem. 30, 4524–4530.
Yin, F.-J., Zhao, H. & Hu, X.-L. (2010). Synth. React. Inorg. Met. Org. Nano-Met. Chem. 40, 606–612.
Naphthalene-1-yl-acetate acid is a plant-growth regulator and exhibits remarkable coordination versatility towards metal cations (Yin et al., 2010; Chen et al., 2004; Yang et al., 2008; Xia et al.,2006; Ji et al., 2011). In continuation of the structural studies of metal complexes of this ligands, the crystal structure of the title compound was determined.
The molecular structure of the title compound (I) (see Figs. 1 & 2), contains a centrosymmetric dinuclear copper paddle-wheel unit, in which each CuII ion is coordinated by four O atoms from a naphthalen-1-yl-acetate ligand in the basal plane and one O atom of a N,N-dimethylformamide ligand in the axial position to form a square-pyramidal coordination geometry. Both independent molecules lie on crystallographic inversion centers.