Bis­[(acetato-κO)­bis(2,2′-bi­pyridine-κ2N,N′)copper(II)] 4-carboxy­phenoxy­acetate hexahydrate

Gao, S.; Huo, L.-H.; Gu, C.-S.; Zhao, H.; Ng, S.W.

doi:10.1107/S160053680402327X

Bis[(acetato-κO)bis(2,2′-bipyridine-κ²N,N′)copper(II)] 4-carboxyphenoxyacetate hexahydrate

S. Gao, L.-H. Huo, C.-S. Gu, H. Zhao and S. W. Ng

The Cu atoms in the two independent cations of the title compound, [Cu(C₂H₃O₂)(C₁₀H₈N₂)₂]₂(C₉H₆O₅)·6H₂O, show square-pyramidal coordination, with one N atom of a chelating heterocycle occupying the apical site. The anions interact, via hydrogen bonds, with the solvent water molecules to form sheets, and the cations occupy the spaces between the sheets.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680402327X/su6144sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680402327X/su6144Isup2.hkl Contains datablock I

CCDC reference: 252790

checkCIF report

Key indicators

Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.004 Å
R factor = 0.046
wR factor = 0.106
Data-to-parameter ratio = 16.1

checkCIF/PLATON results

No syntax errors found



Alert level B
ABSTM02_ALERT_3_B  The ratio of expected to reported Tmax/Tmin(RR') is < 0.75
            Tmin and Tmax reported:      0.490     0.851
            Tmin' and Tmax expected:      0.706     0.847
            RR' =      0.690
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large .............       0.69
PLAT417_ALERT_2_B Short Inter D-H..H-D       H3W2   ..  H3W2    ..       1.58 Ang.

Alert level C
CELLV02_ALERT_1_C  The supplied cell volume s.u. differs from that
            calculated from the cell parameter s.u.'s by > 2
            Calculated cell volume su =      10.64
            Cell volume su given      =       7.00
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N6     -   C34     ..       5.31 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O9     -   C53     ..       5.26 su
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors  for         O2
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors  for         O4
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors  for         C1
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors  for        C23
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.10
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         10
            N3  -CU1 -N1  -C3     70.90  1.10   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         14
            N3  -CU1 -N1  -C7   -107.70  1.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         26
            N1  -CU1 -N3  -C17    -2.10  1.10   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         30
            N1  -CU1 -N3  -C13  -178.00 41.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         42
            N7  -CU2 -N5  -C29   151.40  0.50   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         46
            N7  -CU2 -N5  -C25   -26.80  0.70   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         58
            N5  -CU2 -N7  -C39   -43.70  0.70   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         62
            N5  -CU2 -N7  -C35   128.40  0.60   1.555   1.555   1.555   1.555
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         12
PLAT731_ALERT_1_C Bond    Calc     0.85(3), Rep   0.840(10) ......       3.00 su-Rat
              O1W  -H1W1    1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.86(3), Rep   0.860(10) ......       3.00 su-Rat
              O1W  -H1W2    1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.84(3), Rep   0.840(10) ......       3.00 su-Rat
              O3W  -H3W1    1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.85(4), Rep   0.840(10) ......       4.00 su-Rat
              O4W  -H4W1    1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.85(3), Rep   0.860(10) ......       3.00 su-Rat
              O5W  -H5W1    1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.85(3), Rep   0.850(10) ......       3.00 su-Rat
              O5W  -H5W2    1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.85(3), Rep   0.850(10) ......       3.00 su-Rat
              O6W  -H6W1    1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.85(3), Rep   0.850(10) ......       3.00 su-Rat
              O6W  -H6W2    1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.86(3), Rep   0.860(10) ......       3.00 su-Rat
              O1W  -H2#     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(3), Rep   0.840(10) ......       3.00 su-Rat
              O1W  -H1#     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.84(3), Rep   0.840(10) ......       3.00 su-Rat
              O3W  -H5#     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(4), Rep   0.840(10) ......       4.00 su-Rat
              O4W  -H7#     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(3), Rep   0.860(10) ......       3.00 su-Rat
              O5W  -H9#     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(3), Rep   0.850(10) ......       3.00 su-Rat
              O5W  -H10#    1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(3), Rep   0.850(10) ......       3.00 su-Rat
              O6W  -H11#    1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(3), Rep   0.850(10) ......       3.00 su-Rat
              O6W  -H12#    1.555   1.555
PLAT736_ALERT_1_C H...A   Calc     1.91(3), Rep   1.900(10) ......       3.00 su-Rat
              H2#  -O5      1.555   1.555
PLAT736_ALERT_1_C H...A   Calc     2.08(3), Rep   2.080(10) ......       3.00 su-Rat
              H1#  -O3W     1.555   1.555
PLAT736_ALERT_1_C H...A   Calc     2.00(3), Rep   2.000(10) ......       3.00 su-Rat
              H5#  -O9      1.555   1.556
PLAT736_ALERT_1_C H...A   Calc     1.95(4), Rep   1.950(10) ......       4.00 su-Rat
              H10# -O1W     1.555   2.666
PLAT736_ALERT_1_C H...A   Calc     1.91(3), Rep   1.910(10) ......       3.00 su-Rat
              H11# -O9      1.555   1.555
PLAT736_ALERT_1_C H...A   Calc     1.97(4), Rep   1.970(10) ......       4.00 su-Rat
              H12# -O2W     1.555   1.554

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

  25 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   8 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   9 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Bis[(acetato-κO)bis(2,2'-bipyridine-κ²N,N')copper(II)] 4-carboxyphenoxyacetate hexahydrate top

Crystal data top

[Cu(C₂H₃O₂)(C₁₀H₈N₂)₂]₂(C₉H₆O₅)_.6H₂O	Z = 2
M_r = 1172.14	F(000) = 1216
Triclinic, P1	D_x = 1.462 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 14.385 (2) Å	Cell parameters from 24035 reflections
b = 14.605 (2) Å	θ = 3.3–27.4°
c = 14.655 (2) Å	µ = 0.88 mm⁻¹
α = 86.95 (3)°	T = 295 K
β = 67.22 (3)°	Prism, colorless
γ = 70.38 (3)°	0.39 × 0.26 × 0.19 mm
V = 2663.5 (7) Å³

Data collection top

Rigaku R-AXIS RAPID diffractometer	11950 independent reflections
Radiation source: fine-focus sealed tube	7589 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
ω scans	θ_max = 27.4°, θ_min = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −18→18
T_min = 0.490, T_max = 0.851	k = −18→18
25444 measured reflections	l = −16→18

Refinement top

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.106	H-atom parameters constrained
S = 0.98	w = 1/[σ²(F_o²) + (0.0562P)²] where P = (F_o² + 2F_c²)/3
11950 reflections	(Δ/σ)_max = 0.001
741 parameters	Δρ_max = 0.36 e Å⁻³
18 restraints	Δρ_min = −0.20 e Å⁻³

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cu1	0.34160 (2)	0.15188 (2)	0.23992 (2)	0.03732 (10)
Cu2	0.15910 (2)	0.37476 (2)	0.73343 (2)	0.03987 (10)
O1	0.39016 (16)	0.01175 (13)	0.26043 (13)	0.0497 (5)
O2	0.48471 (18)	0.05024 (17)	0.33051 (15)	0.0673 (6)
O3	0.11679 (16)	0.51769 (14)	0.74172 (13)	0.0528 (5)
O4	0.04669 (18)	0.50305 (17)	0.63510 (15)	0.0686 (6)
O5	0.18415 (17)	0.82297 (17)	0.88636 (13)	0.0676 (6)
O6	0.06630 (16)	0.91883 (15)	0.82880 (13)	0.0554 (5)
O7	0.17930 (16)	0.83757 (15)	0.64672 (12)	0.0565 (5)
O8	0.46961 (18)	0.61600 (19)	0.21591 (15)	0.0793 (7)
O9	0.32143 (19)	0.69885 (16)	0.19503 (14)	0.0692 (6)
O1w	0.38179 (18)	0.68106 (18)	0.84137 (16)	0.0669 (6)
H1w1	0.389 (2)	0.657 (3)	0.8930 (16)	0.100*
H1w2	0.3167 (13)	0.718 (2)	0.856 (2)	0.100*
O2w	0.0358 (2)	0.88652 (17)	1.07831 (15)	0.0785 (7)
H2w1	0.079 (3)	0.871 (2)	1.0178 (12)	0.118*
H2w2	0.006 (3)	0.9481 (8)	1.088 (3)	0.118*
O3w	0.4522 (3)	0.6069 (2)	0.99971 (17)	0.0984 (9)
H3w1	0.413 (3)	0.636 (3)	1.0569 (16)	0.148*
H3w2	0.454 (4)	0.5477 (12)	0.999 (3)	0.148*
O4w	−0.0390 (2)	0.99179 (19)	0.67893 (17)	0.0721 (6)
H4w1	0.000 (3)	0.956 (2)	0.707 (2)	0.108*
H4w2	−0.071 (3)	1.0484 (12)	0.710 (2)	0.108*
O5w	0.6052 (3)	0.4695 (2)	0.27852 (19)	0.0919 (8)
H5w1	0.565 (3)	0.5218 (16)	0.266 (3)	0.138*
H5w2	0.613 (3)	0.4218 (18)	0.242 (3)	0.138*
O6w	0.1158 (2)	0.8171 (2)	0.22408 (15)	0.0730 (7)
H6w1	0.1800 (14)	0.779 (2)	0.209 (3)	0.110*
H6w2	0.105 (3)	0.835 (3)	0.1721 (17)	0.110*
N1	0.47087 (16)	0.13618 (15)	0.11385 (14)	0.0385 (5)
N2	0.28090 (16)	0.13669 (15)	0.12746 (14)	0.0376 (5)
N3	0.21190 (16)	0.17997 (15)	0.36695 (14)	0.0383 (5)
N4	0.30879 (16)	0.29761 (15)	0.26840 (14)	0.0358 (5)
N5	0.02072 (17)	0.38103 (16)	0.84684 (16)	0.0455 (6)
N6	0.20416 (17)	0.36082 (15)	0.86259 (14)	0.0395 (5)
N7	0.28905 (17)	0.35918 (16)	0.60729 (15)	0.0411 (5)
N8	0.19630 (16)	0.23346 (15)	0.69031 (14)	0.0382 (5)
C1	0.4515 (2)	−0.0086 (2)	0.30718 (18)	0.0481 (7)
C2	0.4833 (3)	−0.1125 (2)	0.3354 (3)	0.0761 (10)
H2a	0.5601	−0.1399	0.3122	0.114*
H2b	0.4579	−0.1507	0.3057	0.114*
H2c	0.4522	−0.1126	0.4064	0.114*
C3	0.5646 (2)	0.1347 (2)	0.1120 (2)	0.0512 (7)
H3	0.5716	0.1388	0.1720	0.061*
C4	0.6519 (2)	0.1273 (2)	0.0247 (2)	0.0580 (8)
H4	0.7161	0.1274	0.0257	0.070*
C5	0.6418 (2)	0.1198 (2)	−0.0632 (2)	0.0573 (8)
H5	0.6997	0.1139	−0.1231	0.069*
C6	0.5454 (2)	0.1212 (2)	−0.06268 (19)	0.0510 (7)
H6	0.5374	0.1169	−0.1222	0.061*
C7	0.4604 (2)	0.12889 (17)	0.02731 (17)	0.0384 (6)
C8	0.3553 (2)	0.12765 (17)	0.03446 (17)	0.0371 (6)
C9	0.3335 (3)	0.1168 (2)	−0.0476 (2)	0.0522 (7)
H9	0.3853	0.1116	−0.1113	0.063*
C10	0.2347 (3)	0.1137 (2)	−0.0341 (2)	0.0598 (8)
H10	0.2189	0.1064	−0.0885	0.072*
C11	0.1597 (2)	0.1214 (2)	0.0605 (2)	0.0589 (8)
H11	0.0923	0.1192	0.0713	0.071*
C12	0.1857 (2)	0.1322 (2)	0.1392 (2)	0.0473 (7)
H12	0.1348	0.1367	0.2034	0.057*
C13	0.1668 (2)	0.1138 (2)	0.41031 (19)	0.0489 (7)
H13	0.1933	0.0517	0.3781	0.059*
C14	0.0814 (2)	0.1358 (2)	0.5022 (2)	0.0560 (8)
H14	0.0504	0.0893	0.5308	0.067*
C15	0.0437 (2)	0.2265 (2)	0.5500 (2)	0.0550 (8)
H15	−0.0121	0.2417	0.6124	0.066*
C16	0.0887 (2)	0.2959 (2)	0.50530 (18)	0.0460 (7)
H16	0.0632	0.3583	0.5366	0.055*
C17	0.17323 (19)	0.26990 (19)	0.41218 (16)	0.0363 (6)
C18	0.22528 (19)	0.33838 (18)	0.35559 (17)	0.0346 (6)
C19	0.1934 (2)	0.4354 (2)	0.3864 (2)	0.0480 (7)
H19	0.1360	0.4622	0.4463	0.058*
C20	0.2481 (2)	0.4924 (2)	0.3268 (2)	0.0562 (8)
H20	0.2279	0.5581	0.3464	0.067*
C21	0.3322 (2)	0.4518 (2)	0.2386 (2)	0.0529 (7)
H21	0.3694	0.4894	0.1975	0.063*
C22	0.3605 (2)	0.35490 (19)	0.21194 (18)	0.0425 (6)
H22	0.4180	0.3275	0.1522	0.051*
C23	0.0688 (2)	0.5525 (2)	0.6836 (2)	0.0508 (7)
C24	0.0398 (3)	0.6609 (2)	0.6770 (3)	0.0787 (11)
H24a	0.0710	0.6738	0.6089	0.118*
H24b	0.0667	0.6871	0.7161	0.118*
H24c	−0.0368	0.6908	0.7016	0.118*
C25	−0.0678 (2)	0.3869 (2)	0.8328 (2)	0.0612 (8)
H25	−0.0663	0.3912	0.7688	0.073*
C26	−0.1603 (3)	0.3869 (2)	0.9097 (3)	0.0749 (11)
H26	−0.2201	0.3892	0.8980	0.090*
C27	−0.1625 (3)	0.3834 (3)	1.0041 (3)	0.0790 (12)
H27	−0.2246	0.3840	1.0575	0.095*
C28	−0.0736 (3)	0.3789 (2)	1.0199 (2)	0.0641 (9)
H28	−0.0753	0.3776	1.0840	0.077*
C29	0.0194 (2)	0.37646 (18)	0.93924 (19)	0.0428 (6)
C30	0.1201 (2)	0.37077 (18)	0.94878 (17)	0.0412 (6)
C31	0.1283 (3)	0.3763 (2)	1.0393 (2)	0.0552 (8)
H31	0.0690	0.3835	1.0984	0.066*
C32	0.2238 (3)	0.3711 (2)	1.0410 (2)	0.0649 (9)
H32	0.2302	0.3739	1.1014	0.078*
C33	0.3102 (3)	0.3619 (2)	0.9541 (2)	0.0603 (8)
H33	0.3757	0.3592	0.9541	0.072*
C34	0.2969 (2)	0.35683 (19)	0.8658 (2)	0.0479 (7)
H34	0.3553	0.3503	0.8062	0.058*
C35	0.3294 (2)	0.4295 (2)	0.5694 (2)	0.0560 (8)
H35	0.3032	0.4885	0.6074	0.067*
C36	0.4088 (2)	0.4166 (2)	0.4756 (3)	0.0648 (9)
H36	0.4357	0.4664	0.4506	0.078*
C37	0.4476 (2)	0.3303 (2)	0.4197 (2)	0.0545 (8)
H37	0.5002	0.3212	0.3557	0.065*
C38	0.4086 (2)	0.2566 (2)	0.45850 (18)	0.0457 (7)
H38	0.4350	0.1968	0.4220	0.055*
C39	0.32882 (19)	0.27381 (19)	0.55341 (17)	0.0361 (6)
C40	0.28102 (19)	0.19929 (18)	0.60240 (17)	0.0365 (6)
C41	0.3191 (2)	0.1042 (2)	0.56409 (19)	0.0491 (7)
H41	0.3780	0.0825	0.5041	0.059*
C42	0.2684 (3)	0.0410 (2)	0.6161 (2)	0.0606 (9)
H42	0.2928	−0.0237	0.5913	0.073*
C43	0.1817 (2)	0.0749 (2)	0.7048 (2)	0.0572 (8)
H43	0.1462	0.0336	0.7405	0.069*
C44	0.1486 (2)	0.1704 (2)	0.73972 (19)	0.0467 (7)
H44	0.0905	0.1927	0.8002	0.056*
C45	0.1498 (2)	0.8526 (2)	0.81959 (19)	0.0439 (7)
C46	0.2226 (2)	0.7971 (2)	0.71766 (18)	0.0520 (7)
H46a	0.2937	0.8012	0.6978	0.062*
H46b	0.2291	0.7289	0.7210	0.062*
C47	0.2327 (2)	0.7949 (2)	0.55087 (18)	0.0457 (7)
C48	0.3258 (2)	0.7155 (2)	0.51860 (19)	0.0548 (8)
H48	0.3571	0.6863	0.5625	0.066*
C49	0.3724 (2)	0.6796 (2)	0.41917 (19)	0.0505 (7)
H49	0.4368	0.6273	0.3967	0.061*
C50	0.3259 (2)	0.7192 (2)	0.35294 (18)	0.0435 (7)
C51	0.2322 (2)	0.7991 (2)	0.38747 (19)	0.0545 (8)
H51	0.1998	0.8277	0.3441	0.065*
C52	0.1860 (2)	0.8372 (2)	0.4853 (2)	0.0544 (8)
H52	0.1234	0.8913	0.5072	0.065*
C53	0.3767 (3)	0.6756 (2)	0.2458 (2)	0.0510 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.03765 (18)	0.03884 (19)	0.02918 (15)	−0.01282 (15)	−0.00619 (13)	−0.00247 (12)
Cu2	0.04063 (19)	0.0417 (2)	0.03410 (16)	−0.01322 (15)	−0.01143 (14)	−0.00238 (13)
O1	0.0598 (13)	0.0413 (11)	0.0439 (10)	−0.0116 (10)	−0.0209 (10)	0.0023 (8)
O2	0.0810 (16)	0.0682 (15)	0.0562 (12)	−0.0306 (13)	−0.0246 (12)	−0.0069 (11)
O3	0.0703 (14)	0.0430 (12)	0.0397 (10)	−0.0109 (10)	−0.0225 (10)	−0.0020 (8)
O4	0.0721 (15)	0.0719 (16)	0.0612 (13)	−0.0200 (13)	−0.0277 (12)	−0.0102 (11)
O5	0.0666 (14)	0.0772 (16)	0.0367 (10)	0.0026 (12)	−0.0191 (10)	−0.0057 (10)
O6	0.0496 (12)	0.0553 (13)	0.0416 (10)	−0.0044 (11)	−0.0086 (9)	−0.0002 (9)
O7	0.0601 (13)	0.0563 (13)	0.0353 (9)	0.0066 (10)	−0.0208 (9)	−0.0123 (9)
O8	0.0575 (15)	0.103 (2)	0.0529 (12)	−0.0139 (14)	−0.0039 (11)	−0.0249 (13)
O9	0.0887 (17)	0.0710 (16)	0.0402 (11)	−0.0139 (13)	−0.0276 (12)	−0.0040 (10)
O1w	0.0569 (14)	0.0707 (17)	0.0650 (13)	−0.0200 (12)	−0.0156 (11)	−0.0070 (12)
O2w	0.0969 (19)	0.0670 (16)	0.0381 (11)	−0.0113 (15)	−0.0058 (11)	−0.0005 (10)
O3w	0.115 (2)	0.108 (2)	0.0470 (13)	−0.030 (2)	−0.0106 (14)	−0.0155 (14)
O4w	0.0751 (17)	0.0704 (17)	0.0736 (15)	−0.0192 (14)	−0.0359 (13)	−0.0014 (13)
O5w	0.136 (3)	0.0674 (17)	0.0767 (17)	−0.0403 (19)	−0.0411 (17)	−0.0020 (14)
O6w	0.0731 (16)	0.093 (2)	0.0480 (11)	−0.0253 (15)	−0.0203 (11)	−0.0051 (12)
N1	0.0369 (12)	0.0379 (12)	0.0350 (11)	−0.0139 (10)	−0.0065 (9)	−0.0041 (9)
N2	0.0383 (12)	0.0352 (12)	0.0356 (10)	−0.0119 (10)	−0.0109 (9)	0.0013 (9)
N3	0.0402 (12)	0.0429 (13)	0.0304 (10)	−0.0184 (11)	−0.0085 (9)	−0.0003 (9)
N4	0.0391 (12)	0.0378 (12)	0.0312 (10)	−0.0159 (10)	−0.0120 (9)	0.0011 (9)
N5	0.0383 (13)	0.0439 (14)	0.0480 (13)	−0.0129 (11)	−0.0094 (10)	−0.0112 (10)
N6	0.0416 (12)	0.0392 (13)	0.0371 (11)	−0.0145 (10)	−0.0145 (10)	0.0047 (9)
N7	0.0377 (12)	0.0416 (13)	0.0449 (12)	−0.0168 (11)	−0.0142 (10)	0.0023 (10)
N8	0.0404 (12)	0.0408 (12)	0.0316 (10)	−0.0149 (10)	−0.0114 (9)	0.0032 (9)
C1	0.0515 (17)	0.0465 (17)	0.0318 (13)	−0.0076 (15)	−0.0082 (13)	−0.0055 (12)
C2	0.089 (3)	0.062 (2)	0.084 (2)	−0.018 (2)	−0.049 (2)	0.0208 (19)
C3	0.0444 (17)	0.0519 (18)	0.0509 (16)	−0.0160 (14)	−0.0107 (13)	−0.0112 (14)
C4	0.0394 (16)	0.0507 (19)	0.072 (2)	−0.0193 (15)	−0.0046 (15)	−0.0093 (15)
C5	0.0512 (18)	0.0496 (18)	0.0510 (17)	−0.0223 (15)	0.0059 (14)	−0.0040 (14)
C6	0.0599 (19)	0.0467 (17)	0.0336 (13)	−0.0219 (15)	−0.0013 (13)	−0.0025 (12)
C7	0.0465 (15)	0.0266 (13)	0.0357 (13)	−0.0129 (12)	−0.0084 (11)	−0.0025 (10)
C8	0.0462 (15)	0.0286 (13)	0.0330 (12)	−0.0112 (12)	−0.0128 (11)	0.0008 (10)
C9	0.067 (2)	0.0516 (18)	0.0387 (14)	−0.0220 (16)	−0.0203 (14)	0.0037 (13)
C10	0.077 (2)	0.060 (2)	0.0575 (18)	−0.0239 (18)	−0.0411 (17)	0.0047 (15)
C11	0.0501 (18)	0.057 (2)	0.077 (2)	−0.0180 (16)	−0.0325 (17)	0.0023 (16)
C12	0.0416 (16)	0.0445 (17)	0.0503 (15)	−0.0129 (13)	−0.0136 (13)	0.0010 (13)
C13	0.0498 (17)	0.0502 (18)	0.0446 (15)	−0.0225 (15)	−0.0121 (13)	0.0062 (13)
C14	0.0524 (18)	0.069 (2)	0.0469 (16)	−0.0323 (17)	−0.0108 (14)	0.0138 (15)
C15	0.0474 (17)	0.075 (2)	0.0356 (14)	−0.0242 (17)	−0.0053 (12)	0.0011 (14)
C16	0.0412 (15)	0.0557 (18)	0.0352 (13)	−0.0147 (14)	−0.0092 (12)	−0.0059 (12)
C17	0.0316 (13)	0.0483 (16)	0.0290 (11)	−0.0140 (12)	−0.0113 (10)	0.0006 (11)
C18	0.0315 (13)	0.0387 (15)	0.0334 (12)	−0.0099 (11)	−0.0139 (10)	−0.0014 (11)
C19	0.0435 (16)	0.0441 (17)	0.0489 (15)	−0.0105 (14)	−0.0128 (13)	−0.0083 (13)
C20	0.0587 (19)	0.0394 (17)	0.0704 (19)	−0.0199 (15)	−0.0221 (16)	0.0001 (14)
C21	0.0528 (18)	0.0460 (18)	0.0589 (17)	−0.0244 (15)	−0.0149 (14)	0.0075 (14)
C22	0.0403 (15)	0.0438 (16)	0.0392 (13)	−0.0163 (13)	−0.0098 (12)	0.0025 (12)
C23	0.0484 (17)	0.0545 (19)	0.0372 (14)	−0.0115 (15)	−0.0091 (13)	0.0008 (14)
C24	0.099 (3)	0.056 (2)	0.088 (2)	−0.019 (2)	−0.050 (2)	0.0152 (19)
C25	0.0460 (18)	0.058 (2)	0.077 (2)	−0.0154 (16)	−0.0200 (16)	−0.0162 (16)
C26	0.0422 (19)	0.058 (2)	0.114 (3)	−0.0207 (17)	−0.0138 (19)	−0.011 (2)
C27	0.048 (2)	0.065 (2)	0.097 (3)	−0.0244 (18)	0.003 (2)	0.017 (2)
C28	0.057 (2)	0.060 (2)	0.0522 (17)	−0.0197 (17)	0.0012 (15)	0.0134 (15)
C29	0.0469 (16)	0.0292 (14)	0.0429 (14)	−0.0131 (12)	−0.0076 (12)	0.0008 (11)
C30	0.0528 (17)	0.0318 (14)	0.0338 (13)	−0.0136 (13)	−0.0126 (12)	0.0028 (11)
C31	0.076 (2)	0.0447 (18)	0.0367 (14)	−0.0166 (16)	−0.0171 (15)	0.0033 (12)
C32	0.098 (3)	0.049 (2)	0.0537 (18)	−0.0141 (19)	−0.046 (2)	0.0054 (15)
C33	0.074 (2)	0.0467 (19)	0.076 (2)	−0.0180 (17)	−0.0479 (19)	0.0085 (16)
C34	0.0518 (17)	0.0388 (16)	0.0527 (16)	−0.0156 (14)	−0.0204 (14)	0.0077 (13)
C35	0.0457 (17)	0.0444 (18)	0.073 (2)	−0.0186 (15)	−0.0156 (15)	0.0012 (15)
C36	0.0456 (18)	0.060 (2)	0.085 (2)	−0.0272 (17)	−0.0157 (17)	0.0184 (18)
C37	0.0356 (15)	0.072 (2)	0.0518 (16)	−0.0229 (16)	−0.0100 (13)	0.0146 (16)
C38	0.0363 (15)	0.0564 (18)	0.0404 (14)	−0.0152 (14)	−0.0109 (12)	0.0019 (13)
C39	0.0307 (13)	0.0418 (15)	0.0391 (13)	−0.0143 (12)	−0.0155 (11)	0.0046 (11)
C40	0.0367 (14)	0.0386 (15)	0.0349 (12)	−0.0129 (12)	−0.0144 (11)	−0.0003 (11)
C41	0.0485 (17)	0.0470 (17)	0.0412 (14)	−0.0151 (14)	−0.0066 (12)	−0.0053 (13)
C42	0.069 (2)	0.0404 (17)	0.0616 (18)	−0.0197 (16)	−0.0120 (16)	−0.0061 (14)
C43	0.065 (2)	0.0480 (19)	0.0570 (17)	−0.0267 (16)	−0.0163 (15)	0.0088 (14)
C44	0.0482 (16)	0.0511 (18)	0.0375 (13)	−0.0203 (14)	−0.0111 (12)	0.0072 (12)
C45	0.0460 (17)	0.0433 (17)	0.0366 (14)	−0.0146 (14)	−0.0104 (12)	0.0013 (12)
C46	0.0548 (18)	0.0534 (18)	0.0356 (13)	−0.0021 (15)	−0.0182 (13)	−0.0037 (13)
C47	0.0509 (17)	0.0459 (16)	0.0340 (13)	−0.0094 (14)	−0.0150 (12)	−0.0059 (12)
C48	0.0548 (18)	0.0561 (19)	0.0409 (14)	−0.0014 (15)	−0.0205 (13)	0.0006 (13)
C49	0.0482 (17)	0.0459 (17)	0.0413 (14)	−0.0049 (14)	−0.0096 (13)	−0.0042 (13)
C50	0.0520 (17)	0.0429 (16)	0.0349 (13)	−0.0207 (14)	−0.0120 (12)	−0.0015 (12)
C51	0.0607 (19)	0.060 (2)	0.0416 (14)	−0.0080 (16)	−0.0287 (14)	−0.0037 (14)
C52	0.0549 (18)	0.0512 (19)	0.0458 (15)	0.0026 (15)	−0.0241 (14)	−0.0089 (13)
C53	0.062 (2)	0.0496 (18)	0.0363 (14)	−0.0280 (17)	−0.0053 (14)	−0.0026 (13)

Geometric parameters (Å, º) top

Cu1—O1	1.976 (2)	C13—C14	1.387 (4)
Cu1—N1	2.006 (2)	C13—H13	0.9300
Cu1—N2	2.193 (2)	C14—C15	1.364 (4)
Cu1—N4	2.048 (2)	C14—H14	0.9300
Cu1—N3	1.998 (2)	C15—C16	1.385 (4)
Cu2—O3	1.964 (2)	C15—H15	0.9300
Cu2—N5	2.016 (2)	C16—C17	1.395 (3)
Cu2—N6	2.206 (2)	C16—H16	0.9300
Cu2—N7	2.012 (2)	C17—C18	1.477 (3)
Cu2—N8	2.020 (2)	C18—C19	1.376 (4)
O1—C1	1.267 (3)	C19—C20	1.380 (4)
O2—C1	1.232 (3)	C19—H19	0.9300
O3—C23	1.278 (4)	C20—C21	1.369 (4)
O4—C23	1.230 (3)	C20—H20	0.9300
O5—C45	1.255 (3)	C21—C22	1.367 (4)
O6—C45	1.227 (3)	C21—H21	0.9300
O7—C47	1.374 (3)	C22—H22	0.9300
O7—C46	1.416 (3)	C23—C24	1.503 (4)
O8—C53	1.241 (4)	C24—H24a	0.9600
O9—C53	1.245 (4)	C24—H24b	0.9600
O1w—H1w1	0.84 (1)	C24—H24c	0.9600
O1w—H1w2	0.86 (1)	C25—C26	1.371 (4)
O2w—H2w1	0.85 (1)	C25—H25	0.9300
O2w—H2w2	0.85 (1)	C26—C27	1.370 (5)
O3w—H3w1	0.84 (1)	C26—H26	0.9300
O3w—H3w2	0.86 (1)	C27—C28	1.365 (5)
O4w—H4w1	0.84 (1)	C27—H27	0.9300
O4w—H4w2	0.85 (1)	C28—C29	1.391 (4)
O5w—H5w1	0.86 (1)	C28—H28	0.9300
O5w—H5w2	0.85 (1)	C29—C30	1.484 (4)
O6w—H6w1	0.85 (1)	C30—C31	1.385 (4)
O6w—H6w2	0.85 (1)	C31—C32	1.360 (4)
N1—C3	1.332 (3)	C31—H31	0.9300
N1—C7	1.348 (3)	C32—C33	1.365 (4)
N2—C12	1.337 (3)	C32—H32	0.9300
N2—C8	1.347 (3)	C33—C34	1.389 (4)
N3—C17	1.338 (3)	C33—H33	0.9300
N3—C13	1.340 (3)	C34—H34	0.9300
N4—C22	1.344 (3)	C35—C36	1.378 (4)
N4—C18	1.357 (3)	C35—H35	0.9300
N5—C29	1.345 (3)	C36—C37	1.362 (4)
N5—C25	1.340 (4)	C36—H36	0.9300
N6—C34	1.335 (3)	C37—C38	1.374 (4)
N6—C30	1.341 (3)	C37—H37	0.9300
N7—C39	1.335 (3)	C38—C39	1.386 (3)
N7—C35	1.337 (3)	C38—H38	0.9300
N8—C44	1.347 (3)	C39—C40	1.487 (3)
N8—C40	1.356 (3)	C40—C41	1.371 (4)
C1—C2	1.515 (4)	C41—C42	1.381 (4)
C2—H2a	0.9600	C41—H41	0.9300
C2—H2b	0.9600	C42—C43	1.374 (4)
C2—H2c	0.9600	C42—H42	0.9300
C3—C4	1.380 (4)	C43—C44	1.370 (4)
C3—H3	0.9300	C43—H43	0.9300
C4—C5	1.364 (4)	C44—H44	0.9300
C4—H4	0.9300	C45—C46	1.527 (3)
C5—C6	1.378 (4)	C46—H46a	0.9700
C5—H5	0.9300	C46—H46b	0.9700
C6—C7	1.386 (3)	C47—C48	1.373 (4)
C6—H6	0.9300	C47—C52	1.383 (4)
C7—C8	1.480 (4)	C48—C49	1.392 (4)
C8—C9	1.384 (4)	C48—H48	0.9300
C9—C10	1.374 (4)	C49—C50	1.381 (4)
C9—H9	0.9300	C49—H49	0.9300
C10—C11	1.369 (4)	C50—C51	1.384 (4)
C10—H10	0.9300	C50—C53	1.520 (4)
C11—C12	1.375 (4)	C51—C52	1.381 (4)
C11—H11	0.9300	C51—H51	0.9300
C12—H12	0.9300	C52—H52	0.9300

O1—Cu1—N1	92.96 (9)	C18—C19—H19	120.5
O1—Cu1—N2	96.28 (8)	C20—C19—H19	120.5
O1—Cu1—N3	91.67 (9)	C21—C20—C19	119.7 (3)
O1—Cu1—N4	155.77 (8)	C21—C20—H20	120.2
N1—Cu1—N2	78.46 (8)	C19—C20—H20	120.2
N1—Cu1—N3	174.85 (8)	C22—C21—C20	118.9 (2)
N1—Cu1—N4	94.85 (9)	C22—C21—H21	120.6
N2—Cu1—N3	103.30 (8)	C20—C21—H21	120.6
N2—Cu1—N4	107.74 (8)	N4—C22—C21	122.8 (2)
N3—Cu1—N4	80.00 (9)	N4—C22—H22	118.6
O3—Cu2—N5	91.58 (9)	C21—C22—H22	118.6
O3—Cu2—N6	93.97 (8)	O4—C23—O3	124.0 (3)
O3—Cu2—N7	92.38 (9)	O4—C23—C24	120.5 (3)
O3—Cu2—N8	164.46 (8)	O3—C23—C24	115.5 (3)
N5—Cu2—N6	77.76 (9)	C23—C24—H24a	109.5
N5—Cu2—N7	171.03 (9)	C23—C24—H24b	109.5
N5—Cu2—N8	93.70 (9)	H24a—C24—H24b	109.5
N6—Cu2—N7	109.96 (8)	C23—C24—H24c	109.5
N6—Cu2—N8	101.42 (9)	H24a—C24—H24c	109.5
N7—Cu2—N8	80.48 (9)	H24b—C24—H24c	109.5
C1—O1—Cu1	112.64 (18)	N5—C25—C26	122.3 (3)
C23—O3—Cu2	110.21 (19)	N5—C25—H25	118.9
C47—O7—C46	118.1 (2)	C26—C25—H25	118.9
H1w1—O1w—H1w2	110 (2)	C25—C26—C27	118.4 (3)
H2w1—O2w—H2w2	109 (2)	C25—C26—H26	120.8
H3w1—O3w—H3w2	110 (2)	C27—C26—H26	120.8
H4w1—O4w—H4w2	110 (2)	C28—C27—C26	120.1 (3)
H5w1—O5w—H5w2	109 (2)	C28—C27—H27	119.9
H6w1—O6w—H6w2	110 (2)	C26—C27—H27	119.9
C3—N1—C7	119.1 (2)	C27—C28—C29	119.4 (3)
C3—N1—Cu1	123.25 (18)	C27—C28—H28	120.3
C7—N1—Cu1	117.61 (17)	C29—C28—H28	120.3
C12—N2—C8	118.4 (2)	N5—C29—C28	120.2 (3)
C12—N2—Cu1	129.57 (18)	N5—C29—C30	116.4 (2)
C8—N2—Cu1	111.96 (16)	C28—C29—C30	123.4 (3)
C17—N3—C13	119.6 (2)	N6—C30—C31	121.5 (3)
C17—N3—Cu1	116.09 (15)	N6—C30—C29	115.1 (2)
C13—N3—Cu1	124.20 (18)	C31—C30—C29	123.4 (2)
C22—N4—C18	118.1 (2)	C32—C31—C30	119.4 (3)
C22—N4—Cu1	127.62 (17)	C32—C31—H31	120.3
C18—N4—Cu1	114.32 (16)	C30—C31—H31	120.3
C29—N5—C25	119.6 (2)	C31—C32—C33	120.2 (3)
C29—N5—Cu2	117.98 (18)	C31—C32—H32	119.9
C25—N5—Cu2	122.4 (2)	C33—C32—H32	119.9
C34—N6—C30	118.2 (2)	C32—C33—C34	117.7 (3)
C34—N6—Cu2	128.82 (18)	C32—C33—H33	121.1
C30—N6—Cu2	112.33 (17)	C34—C33—H33	121.1
C39—N7—C35	118.9 (2)	N6—C34—C33	123.0 (3)
C39—N7—Cu2	115.07 (16)	N6—C34—H34	118.5
C35—N7—Cu2	125.58 (19)	C33—C34—H34	118.5
C44—N8—C40	117.5 (2)	N7—C35—C36	121.6 (3)
C44—N8—Cu2	127.50 (17)	N7—C35—H35	119.2
C40—N8—Cu2	114.95 (16)	C36—C35—H35	119.2
O2—C1—O1	124.1 (3)	C37—C36—C35	119.5 (3)
O2—C1—C2	119.7 (3)	C37—C36—H36	120.3
O1—C1—C2	116.1 (3)	C35—C36—H36	120.3
C1—C2—H2a	109.5	C36—C37—C38	119.5 (3)
C1—C2—H2b	109.5	C36—C37—H37	120.3
H2a—C2—H2b	109.5	C38—C37—H37	120.3
C1—C2—H2c	109.5	C37—C38—C39	118.4 (3)
H2a—C2—H2c	109.5	C37—C38—H38	120.8
H2b—C2—H2c	109.5	C39—C38—H38	120.8
N1—C3—C4	122.7 (3)	N7—C39—C38	122.1 (2)
N1—C3—H3	118.7	N7—C39—C40	115.1 (2)
C4—C3—H3	118.7	C38—C39—C40	122.8 (2)
C5—C4—C3	118.5 (3)	N8—C40—C41	122.4 (2)
C5—C4—H4	120.7	N8—C40—C39	113.8 (2)
C3—C4—H4	120.7	C41—C40—C39	123.8 (2)
C4—C5—C6	119.6 (3)	C40—C41—C42	118.9 (2)
C4—C5—H5	120.2	C40—C41—H41	120.5
C6—C5—H5	120.2	C42—C41—H41	120.5
C5—C6—C7	119.4 (3)	C43—C42—C41	119.3 (3)
C5—C6—H6	120.3	C43—C42—H42	120.3
C7—C6—H6	120.3	C41—C42—H42	120.3
N1—C7—C6	120.7 (3)	C44—C43—C42	118.9 (3)
N1—C7—C8	116.5 (2)	C44—C43—H43	120.6
C6—C7—C8	122.9 (2)	C42—C43—H43	120.6
N2—C8—C9	121.3 (2)	N8—C44—C43	122.9 (2)
N2—C8—C7	115.4 (2)	N8—C44—H44	118.5
C9—C8—C7	123.3 (2)	C43—C44—H44	118.5
C10—C9—C8	119.5 (3)	O6—C45—O5	127.0 (2)
C10—C9—H9	120.3	O6—C45—C46	119.0 (3)
C8—C9—H9	120.3	O5—C45—C46	113.9 (3)
C11—C10—C9	119.2 (3)	O7—C46—C45	109.9 (2)
C11—C10—H10	120.4	O7—C46—H46a	109.7
C9—C10—H10	120.4	C45—C46—H46a	109.7
C10—C11—C12	118.8 (3)	O7—C46—H46b	109.7
C10—C11—H11	120.6	C45—C46—H46b	109.7
C12—C11—H11	120.6	H46a—C46—H46b	108.2
N2—C12—C11	122.8 (3)	O7—C47—C48	124.5 (3)
N2—C12—H12	118.6	O7—C47—C52	115.4 (2)
C11—C12—H12	118.6	C48—C47—C52	120.1 (2)
N3—C13—C14	121.5 (3)	C47—C48—C49	118.9 (3)
N3—C13—H13	119.2	C47—C48—H48	120.5
C14—C13—H13	119.2	C49—C48—H48	120.5
C15—C14—C13	119.2 (3)	C50—C49—C48	122.0 (3)
C15—C14—H14	120.4	C50—C49—H49	119.0
C13—C14—H14	120.4	C48—C49—H49	119.0
C14—C15—C16	119.9 (2)	C49—C50—C51	117.8 (2)
C14—C15—H15	120.1	C49—C50—C53	120.6 (3)
C16—C15—H15	120.1	C51—C50—C53	121.6 (3)
C15—C16—C17	118.3 (3)	C52—C51—C50	121.0 (3)
C15—C16—H16	120.9	C52—C51—H51	119.5
C17—C16—H16	120.9	C50—C51—H51	119.5
N3—C17—C16	121.5 (2)	C47—C52—C51	120.1 (3)
N3—C17—C18	115.11 (19)	C47—C52—H52	119.9
C16—C17—C18	123.4 (2)	C51—C52—H52	119.9
N4—C18—C19	121.7 (2)	O8—C53—O9	124.3 (3)
N4—C18—C17	114.1 (2)	O8—C53—C50	117.5 (3)
C19—C18—C17	124.2 (2)	O9—C53—C50	118.2 (3)
C18—C19—C20	118.9 (2)

N3—Cu1—O1—C1	−90.72 (18)	C17—N3—C13—C14	−1.0 (4)
N1—Cu1—O1—C1	87.00 (18)	Cu1—N3—C13—C14	175.3 (2)
N4—Cu1—O1—C1	−21.7 (3)	N3—C13—C14—C15	−0.9 (5)
N2—Cu1—O1—C1	165.71 (17)	C13—C14—C15—C16	1.8 (5)
N7—Cu2—O3—C23	80.11 (19)	C14—C15—C16—C17	−0.8 (4)
N5—Cu2—O3—C23	−91.84 (19)	C13—N3—C17—C16	2.0 (4)
N8—Cu2—O3—C23	18.1 (4)	Cu1—N3—C17—C16	−174.5 (2)
N6—Cu2—O3—C23	−169.68 (18)	C13—N3—C17—C18	−177.0 (2)
O1—Cu1—N1—C3	−82.9 (2)	Cu1—N3—C17—C18	6.4 (3)
N3—Cu1—N1—C3	70.9 (11)	C15—C16—C17—N3	−1.1 (4)
N4—Cu1—N1—C3	74.2 (2)	C15—C16—C17—C18	177.8 (3)
N2—Cu1—N1—C3	−178.7 (2)	C22—N4—C18—C19	0.0 (4)
O1—Cu1—N1—C7	98.54 (19)	Cu1—N4—C18—C19	179.4 (2)
N3—Cu1—N1—C7	−107.7 (10)	C22—N4—C18—C17	179.7 (2)
N4—Cu1—N1—C7	−104.41 (18)	Cu1—N4—C18—C17	−0.9 (3)
N2—Cu1—N1—C7	2.73 (17)	N3—C17—C18—N4	−3.5 (3)
O1—Cu1—N2—C12	84.2 (2)	C16—C17—C18—N4	177.5 (2)
N3—Cu1—N2—C12	−9.0 (2)	N3—C17—C18—C19	176.1 (2)
N1—Cu1—N2—C12	175.9 (2)	C16—C17—C18—C19	−2.9 (4)
N4—Cu1—N2—C12	−92.6 (2)	N4—C18—C19—C20	0.0 (4)
O1—Cu1—N2—C8	−93.44 (17)	C17—C18—C19—C20	−179.7 (3)
N3—Cu1—N2—C8	173.35 (16)	C18—C19—C20—C21	0.3 (5)
N1—Cu1—N2—C8	−1.69 (16)	C19—C20—C21—C22	−0.5 (5)
N4—Cu1—N2—C8	89.76 (17)	C18—N4—C22—C21	−0.3 (4)
O1—Cu1—N3—C17	151.72 (19)	Cu1—N4—C22—C21	−179.5 (2)
N1—Cu1—N3—C17	−2.1 (11)	C20—C21—C22—N4	0.5 (5)
N4—Cu1—N3—C17	−5.39 (18)	Cu2—O3—C23—O4	4.4 (3)
N2—Cu1—N3—C17	−111.42 (18)	Cu2—O3—C23—C24	−175.4 (2)
O1—Cu1—N3—C13	−24.6 (2)	C29—N5—C25—C26	−1.1 (4)
N1—Cu1—N3—C13	−178 (41)	Cu2—N5—C25—C26	177.1 (2)
N4—Cu1—N3—C13	178.2 (2)	N5—C25—C26—C27	1.8 (5)
N2—Cu1—N3—C13	72.2 (2)	C25—C26—C27—C28	−0.7 (5)
O1—Cu1—N4—C22	111.2 (2)	C26—C27—C28—C29	−1.0 (5)
N3—Cu1—N4—C22	−177.4 (2)	C25—N5—C29—C28	−0.7 (4)
N1—Cu1—N4—C22	2.9 (2)	Cu2—N5—C29—C28	−179.0 (2)
N2—Cu1—N4—C22	−76.5 (2)	C25—N5—C29—C30	−179.6 (2)
O1—Cu1—N4—C18	−68.0 (3)	Cu2—N5—C29—C30	2.1 (3)
N3—Cu1—N4—C18	3.30 (17)	C27—C28—C29—N5	1.7 (4)
N1—Cu1—N4—C18	−176.40 (17)	C27—C28—C29—C30	−179.5 (3)
N2—Cu1—N4—C18	104.19 (17)	C34—N6—C30—C31	−0.3 (4)
O3—Cu2—N5—C29	−92.4 (2)	Cu2—N6—C30—C31	−172.1 (2)
N7—Cu2—N5—C29	151.4 (5)	C34—N6—C30—C29	178.9 (2)
N8—Cu2—N5—C29	102.2 (2)	Cu2—N6—C30—C29	7.2 (3)
N6—Cu2—N5—C29	1.30 (18)	N5—C29—C30—N6	−6.5 (3)
O3—Cu2—N5—C25	89.4 (2)	C28—C29—C30—N6	174.6 (2)
N7—Cu2—N5—C25	−26.8 (7)	N5—C29—C30—C31	172.7 (2)
N8—Cu2—N5—C25	−76.0 (2)	C28—C29—C30—C31	−6.1 (4)
N6—Cu2—N5—C25	−176.9 (2)	N6—C30—C31—C32	−0.3 (4)
O3—Cu2—N6—C34	−84.7 (2)	C29—C30—C31—C32	−179.5 (3)
N7—Cu2—N6—C34	9.3 (2)	C30—C31—C32—C33	0.9 (5)
N5—Cu2—N6—C34	−175.4 (2)	C31—C32—C33—C34	−0.9 (5)
N8—Cu2—N6—C34	93.2 (2)	C30—N6—C34—C33	0.4 (4)
O3—Cu2—N6—C30	85.95 (18)	Cu2—N6—C34—C33	170.5 (2)
N7—Cu2—N6—C30	179.94 (16)	C32—C33—C34—N6	0.2 (4)
N5—Cu2—N6—C30	−4.81 (17)	C39—N7—C35—C36	1.6 (4)
N8—Cu2—N6—C30	−96.16 (18)	Cu2—N7—C35—C36	−170.3 (2)
O3—Cu2—N7—C39	−159.86 (19)	N7—C35—C36—C37	−0.1 (5)
N5—Cu2—N7—C39	−43.7 (7)	C35—C36—C37—C38	−1.4 (5)
N8—Cu2—N7—C39	6.26 (18)	C36—C37—C38—C39	1.2 (4)
N6—Cu2—N7—C39	105.05 (19)	C35—N7—C39—C38	−1.7 (4)
O3—Cu2—N7—C35	12.3 (2)	Cu2—N7—C39—C38	171.0 (2)
N5—Cu2—N7—C35	128.4 (6)	C35—N7—C39—C40	178.6 (2)
N8—Cu2—N7—C35	178.4 (3)	Cu2—N7—C39—C40	−8.7 (3)
N6—Cu2—N7—C35	−82.8 (2)	C37—C38—C39—N7	0.3 (4)
O3—Cu2—N8—C44	−120.7 (3)	C37—C38—C39—C40	−180.0 (3)
N7—Cu2—N8—C44	175.8 (2)	C44—N8—C40—C41	−0.7 (4)
N5—Cu2—N8—C44	−11.1 (2)	Cu2—N8—C40—C41	177.7 (2)
N6—Cu2—N8—C44	67.2 (2)	C44—N8—C40—C39	−179.8 (2)
O3—Cu2—N8—C40	61.0 (4)	Cu2—N8—C40—C39	−1.3 (3)
N7—Cu2—N8—C40	−2.45 (18)	N7—C39—C40—N8	6.6 (3)
N5—Cu2—N8—C40	170.68 (19)	C38—C39—C40—N8	−173.1 (2)
N6—Cu2—N8—C40	−111.07 (18)	N7—C39—C40—C41	−172.4 (3)
Cu1—O1—C1—O2	−5.6 (3)	C38—C39—C40—C41	7.9 (4)
Cu1—O1—C1—C2	173.9 (2)	N8—C40—C41—C42	0.9 (4)
C7—N1—C3—C4	0.9 (4)	C39—C40—C41—C42	179.9 (3)
Cu1—N1—C3—C4	−177.7 (2)	C40—C41—C42—C43	−0.2 (5)
N1—C3—C4—C5	−0.9 (5)	C41—C42—C43—C44	−0.7 (5)
C3—C4—C5—C6	0.8 (4)	C40—N8—C44—C43	−0.2 (4)
C4—C5—C6—C7	−0.8 (4)	Cu2—N8—C44—C43	−178.4 (2)
C3—N1—C7—C6	−0.8 (4)	C42—C43—C44—N8	0.9 (5)
Cu1—N1—C7—C6	177.85 (19)	C47—O7—C46—C45	−178.1 (2)
C3—N1—C7—C8	178.0 (2)	O6—C45—C46—O7	2.3 (4)
Cu1—N1—C7—C8	−3.3 (3)	O5—C45—C46—O7	−178.1 (2)
C5—C6—C7—N1	0.7 (4)	C46—O7—C47—C48	−0.3 (4)
C5—C6—C7—C8	−178.0 (3)	C46—O7—C47—C52	179.5 (3)
C12—N2—C8—C9	1.8 (4)	O7—C47—C48—C49	−179.5 (3)
Cu1—N2—C8—C9	179.7 (2)	C52—C47—C48—C49	0.7 (5)
C12—N2—C8—C7	−177.4 (2)	C47—C48—C49—C50	−2.3 (5)
Cu1—N2—C8—C7	0.5 (3)	C48—C49—C50—C51	2.4 (4)
N1—C7—C8—N2	1.7 (3)	C48—C49—C50—C53	−177.6 (3)
C6—C7—C8—N2	−179.5 (2)	C49—C50—C51—C52	−0.9 (4)
N1—C7—C8—C9	−177.4 (2)	C53—C50—C51—C52	179.0 (3)
C6—C7—C8—C9	1.3 (4)	O7—C47—C52—C51	−179.1 (3)
N2—C8—C9—C10	−1.0 (4)	C48—C47—C52—C51	0.7 (5)
C7—C8—C9—C10	178.2 (3)	C50—C51—C52—C47	−0.6 (5)
C8—C9—C10—C11	−0.1 (5)	C49—C50—C53—O8	−12.8 (4)
C9—C10—C11—C12	0.2 (5)	C51—C50—C53—O8	167.3 (3)
C8—N2—C12—C11	−1.7 (4)	C49—C50—C53—O9	164.5 (3)
Cu1—N2—C12—C11	−179.2 (2)	C51—C50—C53—O9	−15.4 (4)
C10—C11—C12—N2	0.7 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1w2···O5	0.86 (1)	1.90 (1)	2.748 (3)	168 (4)
O1w—H1w1···O3w	0.84 (1)	2.08 (1)	2.898 (4)	162 (3)
O2w—H2w1···O5	0.85 (1)	1.91 (1)	2.762 (3)	174 (4)
O2w—H2w2···O6ⁱ	0.85 (1)	2.07 (2)	2.855 (3)	154 (4)
O3w—H3w1···O9ⁱⁱ	0.84 (1)	2.00 (1)	2.843 (3)	178 (4)
O3w—H3w2···O3wⁱⁱⁱ	0.86 (1)	2.21 (3)	2.959 (7)	146 (5)
O4w—H4w1···O6	0.84 (1)	2.30 (2)	3.081 (3)	155 (3)
O4w—H4w2···O6w^iv	0.85 (1)	2.02 (1)	2.858 (4)	168 (4)
O5w—H5w1···O8	0.86 (1)	1.92 (2)	2.757 (4)	165 (4)
O5w—H5w2···O1w^v	0.85 (1)	1.95 (1)	2.799 (3)	175 (4)
O6w—H6w1···O9	0.85 (1)	1.91 (1)	2.754 (4)	171 (4)
O6w—H6w2···O2w^vi	0.85 (1)	1.97 (1)	2.794 (4)	163 (3)

Symmetry codes: (i) −x, −y+2, −z+2; (ii) x, y, z+1; (iii) −x+1, −y+1, −z+2; (iv) −x, −y+2, −z+1; (v) −x+1, −y+1, −z+1; (vi) x, y, z−1.

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Bis­[(acetato-κO)­bis(2,2′-bi­pyridine-κ2N,N′)copper(II)] 4-carboxy­phenoxy­acetate hexahydrate

Supporting information

Key indicators

checkCIF/PLATON results

Bis[(acetato-κO)bis(2,2′-bipyridine-κ²N,N′)copper(II)] 4-carboxyphenoxyacetate hexahydrate