Bis(μ-biphenyl-2,2′-dicarboxyl­ato)bis­[(2,2′-bipyridine)copper(II)] tetra­hydrate

The title compound, [Cu₂(C₁₄H₈O₄)₂(C₁₀H₈N₂)₂]·4H₂O, contains a centrosymmetric binuclear copper(II) complex, with Cu...Cu = 5.6865 (16) Å. The Cu atom displays a cis-CuN₂O₂ square-planar geometry, although two long (>2.6 Å) Cu...O contacts complete a distorted cis-CuN₂O₄ octa­hedron. The crystal packing is consolidated by O—H...O hydrogen bonds to form infinite chains. One water molecule is disordered over two sites, with occupancy factors of ca 0.7 and 0.3.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• Disorder in solvent or counterion
• R factor = 0.058
• wR factor = 0.132
• Data-to-parameter ratio = 11.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      33.00 Perc.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2
PLAT731_ALERT_1_C Bond    Calc     0.85(5), Rep     0.86(2) ......       2.50 su-Ra
              O5   -H5A     1.555   1.555
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              H2 O
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          3
              H2 O

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          9

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

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

S1. Comment

Binuclear copper(II) complexes have been intensely investigated owing to their potential application as magnetic materials and catalysts (Zhu et al., 2001). Here we present the synthesis and crystal structure of the title compound, (I), [Cu₂(dpa)₂(bipy)₂].4H₂O (dpa = the diphenyl-2,2'dicarboxylato dianion and bipy = 2,2'-bipyridine), which contains a centrosymmetric binuclear complex. The copper(II) atom adopts a distorted square geometry (Table 1, Fig. 1). The bipy ligand shows its classical bidentate coordination mode, albeit with a shorter mean Cu—N bond length than in the related complex [Cu₂(C₂O₄)(C₁₂H₈N₂)₂(C₃H₇NO)₂](ClO₄)₂ (Wang et al., 2006). The dpa ligand adopts a µ₂-bridged coordination and the dihedral angle between its aromatic rings is 86.7 (2)°. As well as the short Cu—O bonds, two long (> 2.60 Å) Cu—O contacts that might be regarded as secondary bonds (He & Zhu, 2003) complete a distorted octahedron. The Cu···Cuⁱ (i = 1 - x, 1 - y, 1 - z) distance bridged by the dpa ligands is 5.6865 (16) Å.

The complex (I) is extended into one dimensional framework by O—H···O hydrogen bonds (Table 2, Fig.2).

Related literature

For related literature, see: He & Zhu (2003); Wang et al. (2006); Zhu et al. (2001).

S2. Experimental

0.0705 g (0.3 mmol) Cu(NO₃)₂.6H₂O, 0.0734 g diphenyl-2,2'-dicarboxyl acid) and 0.0473 g 2,2'-bipyridine were dissolved in 20 ml water, to obtain a blue solution. After about two weeks at room temperature, blue plates of (I) were obtained and filtered off.

S3. Refinement

The C-bound H atoms were positioned geometrically (C—H = 0.93 Å) and refined as riding with U_iso(H) = 1.2U_eq(C). The water H atoms were located in a diference map and refined with a distance restraint of O—H = 0.85 (1) Å and the constraint U_iso(H) = 1.5U_eq(O). Due to the disorder of the water molecules the location of their H atoms should be regarded as less certain.

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures

	Fig. 1. View of the molecular structure of (I) with displacement ellipsoids drawn at the 30% probability level (arbitrary spheres for the H atoms).
	Fig. 2. The one dimensional chain in (I) formed by O—H···O hydrogen bongs. Displacement ellipsoids are drawn at the 30% probability level. The bipy ligands are omitted for clarity.

Bis(µ-biphenyl-2,2'-dicarboxylato)bis[(2,2'-bipyridine)copper(II)] tetrahydrate

Crystal data

[Cu2(C14H8O4)2(C10H8N2)2]·4H2O	F(000) = 1020
Mr = 991.92	Dx = 1.496 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 15487 reflections
a = 11.428 (3) Å	θ = 2.0–25°
b = 9.816 (2) Å	µ = 1.04 mm^−1
c = 19.774 (4) Å	T = 293 K
β = 97.098 (4)°	Plate, blue
V = 2201.2 (9) Å^3	0.19 × 0.12 × 0.02 mm
Z = 2

Data collection

Bruker SMART CCD area-detector diffractometer	3875 independent reflections
Radiation source: fine-focus sealed tube	2635 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.091
ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.827, Tmax = 0.980	k = −11→11
15487 measured reflections	l = −23→23

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.058	Hydrogen site location: difmap and geom
wR(F^2) = 0.132	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0523P)^2] where P = (Fo^2 + 2Fc^2)/3
3875 reflections	(Δ/σ)max < 0.001
326 parameters	Δρmax = 0.40 e Å^−3
9 restraints	Δρmin = −0.39 e Å^−3

Special details

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O3	−0.1297 (3)	−0.3198 (3)	−0.11357 (19)	0.0617 (10)
C24	−0.0584 (4)	−0.2244 (4)	−0.1138 (2)	0.0349 (11)
O4	−0.0740 (2)	−0.1116 (3)	−0.08590 (14)	0.0358 (7)
O5	−0.1362 (3)	0.2058 (4)	−0.02708 (18)	0.0670 (11)
O6	−0.2335 (5)	−0.5841 (6)	−0.1210 (4)	0.095 (3)	0.703 (7)
O6'	−0.1884 (17)	−0.515 (2)	−0.0306 (11)	0.192 (11)	0.297 (7)
H6A	−0.201 (8)	−0.639 (4)	−0.091 (3)	0.288*	0.703 (7)
H6B	−0.204 (8)	−0.505 (3)	−0.112 (5)	0.288*	0.703 (7)
H6B'	−0.202 (6)	−0.53 (3)	−0.073 (3)	0.288*	0.297 (7)
H6A'	−0.114 (3)	−0.51 (3)	−0.020 (5)	0.288*	0.297 (7)
H5B	−0.066 (2)	0.223 (9)	−0.036 (3)	0.288*
H5A	−0.132 (6)	0.170 (8)	0.012 (2)	0.288*
Cu1	0.21213 (4)	0.14650 (5)	0.03932 (2)	0.03214 (16)
O2	0.2010 (2)	0.0042 (3)	−0.07275 (14)	0.0422 (8)
O1	0.1142 (2)	0.1934 (3)	−0.04561 (14)	0.0377 (7)
N2	0.3250 (3)	0.0462 (3)	0.10571 (16)	0.0343 (9)
N1	0.3617 (3)	0.2201 (3)	0.01224 (16)	0.0332 (9)
C18	0.1004 (3)	−0.1420 (4)	−0.1838 (2)	0.0314 (10)
C11	0.1296 (3)	0.0982 (4)	−0.0884 (2)	0.0290 (10)
C5	0.4607 (3)	0.1641 (4)	0.0449 (2)	0.0334 (10)
C12	0.0576 (3)	0.1050 (4)	−0.15634 (19)	0.0305 (10)
C17	0.0412 (3)	−0.0076 (4)	−0.1992 (2)	0.0329 (10)
C23	0.0521 (3)	−0.2448 (4)	−0.1464 (2)	0.0308 (10)
C6	0.4389 (3)	0.0638 (4)	0.0973 (2)	0.0322 (10)
C8	0.4958 (4)	−0.0963 (5)	0.1854 (2)	0.0536 (14)
H8	0.5538	−0.1442	0.2127	0.064*
C16	−0.0338 (4)	0.0043 (5)	−0.2599 (2)	0.0385 (11)
H16	−0.0467	−0.0713	−0.2882	0.046*
C22	0.1106 (4)	−0.3689 (5)	−0.1356 (2)	0.0427 (12)
H22	0.0785	−0.4369	−0.1107	0.051*
C13	0.0006 (4)	0.2268 (4)	−0.1761 (2)	0.0375 (11)
H13	0.0111	0.3026	−0.1479	0.045*
C15	−0.0894 (4)	0.1248 (5)	−0.2792 (2)	0.0487 (13)
H15	−0.1387	0.1307	−0.3202	0.058*
C7	0.5268 (4)	−0.0085 (5)	0.1364 (2)	0.0441 (12)
H7	0.6054	0.0023	0.1297	0.053*
C19	0.2051 (4)	−0.1712 (4)	−0.2100 (2)	0.0408 (12)
H19	0.2373	−0.1056	−0.2362	0.049*
C2	0.4777 (4)	0.3556 (5)	−0.0524 (3)	0.0559 (14)
H2	0.4817	0.4218	−0.0857	0.067*
C20	0.2626 (4)	−0.2930 (5)	−0.1986 (2)	0.0496 (13)
H20	0.3333	−0.3082	−0.2162	0.060*
C10	0.2967 (4)	−0.0408 (4)	0.1524 (2)	0.0430 (12)
H10	0.2174	−0.0530	0.1572	0.052*
C4	0.5699 (4)	0.2020 (5)	0.0290 (2)	0.0472 (13)
H4	0.6378	0.1623	0.0515	0.057*
C14	−0.0716 (4)	0.2355 (5)	−0.2377 (2)	0.0460 (13)
H14	−0.1082	0.3176	−0.2508	0.055*
C1	0.3707 (4)	0.3143 (5)	−0.0355 (2)	0.0507 (13)
H1	0.3024	0.3529	−0.0579	0.061*
C21	0.2161 (4)	−0.3922 (5)	−0.1615 (2)	0.0492 (13)
H21	0.2550	−0.4750	−0.1536	0.059*
C3	0.5780 (4)	0.2990 (5)	−0.0201 (3)	0.0576 (15)
H3	0.6513	0.3257	−0.0313	0.069*
C9	0.3793 (4)	−0.1136 (5)	0.1939 (2)	0.0520 (14)
H9	0.3571	−0.1728	0.2267	0.062*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O3	0.057 (2)	0.043 (2)	0.090 (3)	−0.0187 (17)	0.0289 (19)	−0.0131 (18)
C24	0.036 (2)	0.038 (3)	0.029 (2)	−0.002 (2)	−0.0003 (19)	0.008 (2)
O4	0.0300 (15)	0.0339 (17)	0.0458 (18)	−0.0023 (13)	0.0140 (14)	−0.0038 (14)
O5	0.050 (2)	0.088 (3)	0.063 (2)	0.015 (2)	0.0054 (18)	0.009 (2)
O6	0.071 (4)	0.060 (4)	0.151 (7)	−0.010 (3)	−0.005 (4)	0.038 (4)
O6'	0.24 (2)	0.095 (15)	0.28 (3)	0.015 (15)	0.16 (2)	0.057 (16)
Cu1	0.0225 (3)	0.0413 (3)	0.0322 (3)	0.0016 (2)	0.0020 (2)	0.0023 (3)
O2	0.0353 (17)	0.0431 (18)	0.0443 (19)	0.0077 (14)	−0.0101 (14)	−0.0023 (15)
O1	0.0327 (16)	0.0478 (19)	0.0311 (16)	0.0110 (14)	−0.0023 (13)	−0.0057 (14)
N2	0.0287 (19)	0.044 (2)	0.030 (2)	−0.0011 (16)	0.0006 (15)	0.0037 (17)
N1	0.034 (2)	0.036 (2)	0.029 (2)	−0.0029 (16)	0.0020 (16)	0.0042 (16)
C18	0.031 (2)	0.034 (2)	0.029 (2)	−0.0021 (19)	0.0016 (18)	−0.004 (2)
C11	0.021 (2)	0.032 (2)	0.034 (2)	−0.0012 (18)	0.0039 (18)	0.003 (2)
C5	0.026 (2)	0.036 (3)	0.038 (3)	0.0020 (19)	0.0039 (19)	−0.010 (2)
C12	0.027 (2)	0.038 (3)	0.026 (2)	−0.0052 (18)	0.0019 (17)	0.0020 (19)
C17	0.029 (2)	0.038 (3)	0.033 (2)	−0.0057 (19)	0.0098 (19)	0.004 (2)
C23	0.030 (2)	0.036 (3)	0.027 (2)	−0.0016 (19)	0.0031 (19)	−0.0040 (19)
C6	0.028 (2)	0.036 (2)	0.032 (2)	0.0040 (19)	0.0007 (18)	−0.006 (2)
C8	0.051 (3)	0.058 (3)	0.047 (3)	0.010 (2)	−0.011 (2)	0.011 (3)
C16	0.037 (3)	0.045 (3)	0.033 (3)	−0.002 (2)	−0.001 (2)	0.002 (2)
C22	0.047 (3)	0.041 (3)	0.040 (3)	0.003 (2)	0.006 (2)	−0.003 (2)
C13	0.040 (3)	0.035 (3)	0.038 (3)	−0.001 (2)	0.007 (2)	0.007 (2)
C15	0.042 (3)	0.064 (3)	0.036 (3)	−0.002 (2)	−0.008 (2)	0.012 (2)
C7	0.033 (3)	0.058 (3)	0.040 (3)	0.003 (2)	−0.001 (2)	0.000 (2)
C19	0.035 (2)	0.047 (3)	0.041 (3)	0.000 (2)	0.008 (2)	0.000 (2)
C2	0.061 (3)	0.051 (3)	0.058 (3)	−0.011 (3)	0.019 (3)	0.016 (3)
C20	0.036 (3)	0.066 (3)	0.049 (3)	0.009 (2)	0.012 (2)	−0.007 (3)
C10	0.038 (3)	0.043 (3)	0.048 (3)	−0.002 (2)	0.008 (2)	0.003 (2)
C4	0.032 (3)	0.052 (3)	0.057 (3)	0.000 (2)	0.007 (2)	0.000 (3)
C14	0.045 (3)	0.045 (3)	0.048 (3)	0.008 (2)	0.002 (2)	0.015 (2)
C1	0.048 (3)	0.053 (3)	0.051 (3)	−0.003 (2)	0.008 (2)	0.014 (3)
C21	0.050 (3)	0.046 (3)	0.051 (3)	0.018 (2)	0.003 (2)	−0.006 (2)
C3	0.045 (3)	0.062 (3)	0.069 (4)	−0.005 (3)	0.023 (3)	0.002 (3)
C9	0.054 (3)	0.051 (3)	0.049 (3)	−0.001 (2)	0.000 (2)	0.019 (2)

Geometric parameters (Å, º)

O3—C24	1.242 (5)	C23—C22	1.394 (6)
C24—O4	1.260 (5)	C6—C7	1.385 (5)
C24—C23	1.500 (6)	C8—C9	1.372 (6)
C24—Cu1^i	2.545 (4)	C8—C7	1.375 (6)
O4—Cu1^i	1.953 (3)	C8—H8	0.9300
O5—H5B	0.855 (18)	C16—C15	1.375 (6)
O5—H5A	0.86 (2)	C16—H16	0.9300
O6—H6A	0.85 (2)	C22—C21	1.386 (6)
O6—H6B	0.86 (2)	C22—H22	0.9300
O6—H6B'	1.09 (8)	C13—C14	1.387 (6)
O6'—H6B'	0.85 (2)	C13—H13	0.9300
O6'—H6A'	0.85 (2)	C15—C14	1.361 (6)
Cu1—O4^i	1.953 (3)	C15—H15	0.9300
Cu1—O1	1.955 (3)	C7—H7	0.9300
Cu1—N2	1.984 (3)	C19—C20	1.369 (6)
Cu1—N1	1.989 (3)	C19—H19	0.9300
O2—C11	1.245 (4)	C2—C3	1.360 (6)
O1—C11	1.287 (5)	C2—C1	1.368 (6)
N2—C10	1.326 (5)	C2—H2	0.9300
N2—C6	1.343 (5)	C20—C21	1.366 (6)
N1—C1	1.334 (5)	C20—H20	0.9300
N1—C5	1.348 (5)	C10—C9	1.373 (6)
C18—C19	1.392 (5)	C10—H10	0.9300
C18—C23	1.404 (6)	C4—C3	1.371 (6)
C18—C17	1.496 (5)	C4—H4	0.9300
C11—C12	1.488 (5)	C14—H14	0.9300
C5—C4	1.376 (6)	C1—H1	0.9300
C5—C6	1.474 (6)	C21—H21	0.9300
C12—C17	1.391 (5)	C3—H3	0.9300
C12—C13	1.394 (6)	C9—H9	0.9300
C17—C16	1.392 (5)
O3—C24—O4	122.2 (4)	C7—C6—C5	124.1 (4)
O3—C24—C23	119.2 (4)	C9—C8—C7	120.2 (4)
O4—C24—C23	118.5 (4)	C9—C8—H8	119.9
O3—C24—Cu1^i	74.0 (3)	C7—C8—H8	119.9
O4—C24—Cu1^i	48.49 (19)	C15—C16—C17	121.8 (4)
C23—C24—Cu1^i	165.1 (3)	C15—C16—H16	119.1
C24—O4—Cu1^i	102.6 (2)	C17—C16—H16	119.1
H5B—O5—H5A	109 (3)	C21—C22—C23	120.7 (4)
H6A—O6—H6B	108 (3)	C21—C22—H22	119.7
H6A—O6—H6B'	68 (10)	C23—C22—H22	119.7
H6B—O6—H6B'	48 (10)	C14—C13—C12	120.4 (4)
H6B'—O6'—H6A'	109 (4)	C14—C13—H13	119.8
O4^i—Cu1—O1	92.09 (12)	C12—C13—H13	119.8
O4^i—Cu1—N2	95.61 (13)	C14—C15—C16	119.3 (4)
O1—Cu1—N2	160.33 (13)	C14—C15—H15	120.3
O4^i—Cu1—N1	164.13 (13)	C16—C15—H15	120.3
O1—Cu1—N1	95.89 (12)	C8—C7—C6	118.8 (4)
N2—Cu1—N1	81.29 (13)	C8—C7—H7	120.6
O4^i—Cu1—C24^i	28.88 (12)	C6—C7—H7	120.6
O1—Cu1—C24^i	93.65 (12)	C20—C19—C18	122.4 (4)
N2—Cu1—C24^i	101.82 (13)	C20—C19—H19	118.8
N1—Cu1—C24^i	136.39 (14)	C18—C19—H19	118.8
C11—O1—Cu1	106.5 (2)	C3—C2—C1	119.4 (5)
C10—N2—C6	119.5 (4)	C3—C2—H2	120.3
C10—N2—Cu1	125.8 (3)	C1—C2—H2	120.3
C6—N2—Cu1	114.5 (3)	C21—C20—C19	120.0 (4)
C1—N1—C5	119.2 (4)	C21—C20—H20	120.0
C1—N1—Cu1	125.9 (3)	C19—C20—H20	120.0
C5—N1—Cu1	114.9 (3)	N2—C10—C9	122.8 (4)
C19—C18—C23	117.4 (4)	N2—C10—H10	118.6
C19—C18—C17	119.6 (4)	C9—C10—H10	118.6
C23—C18—C17	122.9 (4)	C3—C4—C5	119.4 (4)
O2—C11—O1	120.9 (4)	C3—C4—H4	120.3
O2—C11—C12	122.0 (4)	C5—C4—H4	120.3
O1—C11—C12	117.1 (3)	C15—C14—C13	120.6 (4)
N1—C5—C4	120.8 (4)	C15—C14—H14	119.7
N1—C5—C6	113.9 (3)	C13—C14—H14	119.7
C4—C5—C6	125.3 (4)	N1—C1—C2	121.9 (5)
C17—C12—C13	119.2 (4)	N1—C1—H1	119.1
C17—C12—C11	122.1 (4)	C2—C1—H1	119.1
C13—C12—C11	118.6 (4)	C20—C21—C22	119.7 (4)
C12—C17—C16	118.7 (4)	C20—C21—H21	120.2
C12—C17—C18	123.6 (4)	C22—C21—H21	120.2
C16—C17—C18	117.7 (4)	C2—C3—C4	119.3 (5)
C22—C23—C18	119.8 (4)	C2—C3—H3	120.3
C22—C23—C24	117.7 (4)	C4—C3—H3	120.3
C18—C23—C24	122.5 (4)	C8—C9—C10	117.9 (4)
N2—C6—C7	120.8 (4)	C8—C9—H9	121.1
N2—C6—C5	115.1 (3)	C10—C9—H9	121.1
O3—C24—O4—Cu1^i	7.1 (5)	C17—C18—C23—C24	−5.0 (6)
C23—C24—O4—Cu1^i	−170.9 (3)	O3—C24—C23—C22	−40.9 (6)
O4^i—Cu1—O1—C11	−111.8 (2)	O4—C24—C23—C22	137.2 (4)
N2—Cu1—O1—C11	1.4 (5)	Cu1^i—C24—C23—C22	109.9 (11)
N1—Cu1—O1—C11	81.9 (3)	O3—C24—C23—C18	142.3 (4)
C24^i—Cu1—O1—C11	−140.7 (3)	O4—C24—C23—C18	−39.6 (6)
O4^i—Cu1—N2—C10	15.1 (4)	Cu1^i—C24—C23—C18	−66.9 (12)
O1—Cu1—N2—C10	−97.5 (5)	C10—N2—C6—C7	0.5 (6)
N1—Cu1—N2—C10	179.4 (4)	Cu1—N2—C6—C7	−174.8 (3)
C24^i—Cu1—N2—C10	43.7 (4)	C10—N2—C6—C5	−179.2 (4)
O4^i—Cu1—N2—C6	−170.0 (3)	Cu1—N2—C6—C5	5.6 (5)
O1—Cu1—N2—C6	77.4 (5)	N1—C5—C6—N2	−1.6 (5)
N1—Cu1—N2—C6	−5.7 (3)	C4—C5—C6—N2	177.8 (4)
C24^i—Cu1—N2—C6	−141.4 (3)	N1—C5—C6—C7	178.8 (4)
O4^i—Cu1—N1—C1	−97.5 (6)	C4—C5—C6—C7	−1.8 (7)
O1—Cu1—N1—C1	22.3 (4)	C12—C17—C16—C15	1.6 (6)
N2—Cu1—N1—C1	−177.3 (4)	C18—C17—C16—C15	−178.2 (4)
C24^i—Cu1—N1—C1	−79.3 (4)	C18—C23—C22—C21	−0.1 (6)
O4^i—Cu1—N1—C5	84.6 (6)	C24—C23—C22—C21	−177.0 (4)
O1—Cu1—N1—C5	−155.6 (3)	C17—C12—C13—C14	0.1 (6)
N2—Cu1—N1—C5	4.8 (3)	C11—C12—C13—C14	−177.1 (4)
C24^i—Cu1—N1—C5	102.8 (3)	C17—C16—C15—C14	−0.5 (7)
Cu1—O1—C11—O2	−3.4 (4)	C9—C8—C7—C6	1.4 (7)
Cu1—O1—C11—C12	175.8 (3)	N2—C6—C7—C8	−1.6 (7)
C1—N1—C5—C4	−0.6 (6)	C5—C6—C7—C8	178.0 (4)
Cu1—N1—C5—C4	177.4 (3)	C23—C18—C19—C20	−2.0 (6)
C1—N1—C5—C6	178.8 (4)	C17—C18—C19—C20	−179.0 (4)
Cu1—N1—C5—C6	−3.2 (4)	C18—C19—C20—C21	1.3 (7)
O2—C11—C12—C17	17.5 (6)	C6—N2—C10—C9	0.9 (7)
O1—C11—C12—C17	−161.7 (4)	Cu1—N2—C10—C9	175.6 (3)
O2—C11—C12—C13	−165.4 (4)	N1—C5—C4—C3	0.6 (7)
O1—C11—C12—C13	15.3 (5)	C6—C5—C4—C3	−178.7 (4)
C13—C12—C17—C16	−1.4 (6)	C16—C15—C14—C13	−0.8 (7)
C11—C12—C17—C16	175.7 (4)	C12—C13—C14—C15	1.1 (7)
C13—C12—C17—C18	178.4 (4)	C5—N1—C1—C2	0.1 (7)
C11—C12—C17—C18	−4.5 (6)	Cu1—N1—C1—C2	−177.7 (4)
C19—C18—C17—C12	−94.7 (5)	C3—C2—C1—N1	0.4 (8)
C23—C18—C17—C12	88.5 (5)	C19—C20—C21—C22	0.1 (7)
C19—C18—C17—C16	85.1 (5)	C23—C22—C21—C20	−0.7 (7)
C23—C18—C17—C16	−91.8 (5)	C1—C2—C3—C4	−0.4 (8)
C19—C18—C23—C22	1.4 (6)	C5—C4—C3—C2	−0.1 (8)
C17—C18—C23—C22	178.3 (4)	C7—C8—C9—C10	−0.1 (7)
C19—C18—C23—C24	178.1 (4)	N2—C10—C9—C8	−1.1 (7)

Symmetry code: (i) −x, −y, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O2^i	0.85 (5)	2.29 (7)	3.009 (5)	144 (6)
O5—H5B···O1	0.86 (3)	2.11 (3)	2.932 (4)	160 (8)
O6—H6A···O5^ii	0.85 (6)	2.06 (5)	2.903 (8)	171 (7)
O6—H6B···O3	0.86 (5)	2.01 (5)	2.849 (7)	167 (9)

Symmetry codes: (i) −x, −y, −z; (ii) x, y−1, z.