μ-Oxalato-κ⁴O¹,O²:O^1′,O^2′-bis­[aqua­(2,2′-bipyridyl-κ²N,N′)copper(II)] bis­(hydrogen squarate)

The title compound, [Cu₂(C₂O₄)(C₁₀H₈N₂)₂(H₂O)₂](C₄HO₄)₂, contains a dinuclear μ-oxalato–dicopper(II) complex cation in which the oxalate ligand (ox) bridges the Cu atoms in a bis-bidentate fashion. The square-pyramidal environment of each Cu atom is completed by the two N atoms of the 2,2′-bipyridine ligand (bpy) and by one apical water mol­ecule. The hydrogen squarate counter-anions (Hsq) form cyclic dimeric units through strong O—H...O hydrogen bonds. The crystal structure shows alternating hydrogen-bonded complex cations and cyclic anionic units.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](Wave) = 0.000 Å
• R factor = 0.042
• wR factor = 0.081
• Data-to-parameter ratio = 18.4

checkCIF/PLATON results

No syntax errors found



Alert level C
GOODF01_ALERT_2_C  The least squares goodness of fit parameter lies
            outside the range 0.80 <> 2.00
            Goodness of fit given =      0.764

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

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

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Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis RED (Oxford Diffraction, 2003); data reduction: CrysAlis RED; program(s) used to solve structure: DIRDIF99.2 (Beurskens et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

µ-Oxalato-κ⁴O¹,O²:O^1',O^2'-bis[aqua(2,2'-bipyridyl- κ²N,N')copper(II)] bis(hydrogen squarate)

Crystal data

[Cu2(C2O4)(C10H8N2)2(H2O)2](C4HO4)2	Z = 2
Mr = 789.62	F(000) = 800
Triclinic, P1	Dx = 1.739 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0147 (12) Å	Cell parameters from 6000 reflections
b = 9.2276 (12) Å	θ = 3.5–25°
c = 21.728 (2) Å	µ = 1.49 mm^−1
α = 92.049 (10)°	T = 295 K
β = 94.860 (11)°	Prism, blue
γ = 109.283 (12)°	0.14 × 0.09 × 0.07 mm
V = 1507.9 (4) Å^3

Data collection

Oxford Diffraction Xcalibur diffractometer	8613 independent reflections
Radiation source: fine-focus sealed tube	3850 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
Detector resolution: 1024 × 1024 with blocks 2 × 2 pixels mm^-1	θmax = 30°, θmin = 3.0°
ω scans	h = −8→11
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2003)	k = −12→12
Tmin = 0.719, Tmax = 0.843	l = −30→30
14798 measured reflections

Refinement

Refinement on F^2	6 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.042	w = 1/[σ^2(Fo^2) + (0.028P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.081	(Δ/σ)max = 0.001
S = 0.76	Δρmax = 0.54 e Å^−3
8613 reflections	Δρmin = −0.28 e Å^−3
469 parameters

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.

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

	x	y	z	Uiso*/Ueq
C29	0.5897 (5)	0.3157 (4)	−0.02162 (14)	0.0549 (9)
H29	0.5969	0.2849	−0.0622	0.066*
C28	0.7120 (4)	0.4495 (4)	0.00618 (14)	0.0475 (8)
H28	0.8025	0.5098	−0.0154	0.057*
C26	0.8202 (4)	0.6312 (3)	0.10226 (13)	0.0345 (7)
C5	0.0670 (4)	0.3497 (4)	0.54139 (13)	0.0409 (8)
H5	−0.0186	0.2845	0.5634	0.049*
C4	0.1848 (4)	0.4848 (4)	0.56987 (14)	0.0448 (8)
H4	0.18	0.511	0.6112	0.054*
C33	0.3812 (4)	0.0445 (3)	0.36858 (13)	0.0354 (7)
C40	0.9414 (4)	0.2927 (3)	0.12524 (14)	0.0383 (7)
C23	1.0332 (4)	0.8774 (4)	0.17753 (17)	0.0592 (10)
H23	1.1056	0.9599	0.2039	0.071*
C24	1.0614 (4)	0.8649 (4)	0.11632 (17)	0.0603 (10)
H24	1.1529	0.9407	0.1006	0.072*
C25	0.9564 (4)	0.7425 (4)	0.07861 (15)	0.0530 (9)
H25	0.9761	0.7339	0.0373	0.064*
C11	−0.0940 (4)	0.0297 (3)	0.35031 (14)	0.0414 (7)
H11	−0.0678	0.0208	0.3097	0.05*
C31	0.4503 (4)	0.2772 (3)	0.06985 (13)	0.0453 (8)
H31	0.3592	0.2186	0.0916	0.054*
C6	0.0764 (3)	0.3112 (3)	0.47965 (12)	0.0311 (7)
C37	0.8206 (4)	0.2322 (3)	0.17338 (13)	0.0342 (7)
C10	−0.2258 (4)	−0.0891 (3)	0.37155 (16)	0.0493 (8)
H10	−0.2872	−0.1772	0.3462	0.059*
C36	0.5005 (4)	0.0884 (3)	0.32163 (12)	0.0316 (7)
C7	−0.0384 (3)	0.1688 (3)	0.44412 (12)	0.0321 (7)
C14	0.3445 (4)	0.3206 (3)	0.25724 (12)	0.0283 (6)
C39	0.8500 (4)	0.1442 (4)	0.08631 (15)	0.0468 (8)
C34	0.2992 (4)	−0.1092 (3)	0.33369 (13)	0.0385 (7)
C35	0.4280 (4)	−0.0541 (3)	0.28675 (13)	0.0349 (7)
C38	0.7390 (4)	0.0933 (3)	0.13617 (13)	0.0422 (8)
C30	0.4582 (5)	0.2287 (4)	0.01062 (14)	0.0540 (9)
H30	0.3752	0.1378	−0.0075	0.065*
C8	−0.1715 (4)	0.0559 (4)	0.46737 (15)	0.0444 (8)
H8	−0.1984	0.0679	0.5076	0.053*
C22	0.8944 (4)	0.7641 (3)	0.19846 (14)	0.0488 (8)
H22	0.8728	0.7719	0.2396	0.059*
C13	0.4691 (4)	0.4637 (3)	0.29661 (12)	0.0280 (6)
Cu1	0.19785 (4)	0.33052 (4)	0.362303 (15)	0.03439 (11)
Cu2	0.57777 (5)	0.48169 (4)	0.183733 (15)	0.03888 (12)
N32	0.5689 (3)	0.4062 (2)	0.09794 (10)	0.0334 (6)
N21	0.7892 (3)	0.6429 (3)	0.16202 (10)	0.0353 (6)
N12	−0.0019 (3)	0.1571 (2)	0.38534 (10)	0.0310 (5)
N1	0.2001 (3)	0.4058 (3)	0.44787 (10)	0.0307 (5)
O4	0.3831 (2)	0.2986 (2)	0.20403 (8)	0.0371 (5)
O3	0.6024 (2)	0.5465 (2)	0.27259 (8)	0.0370 (5)
O1	0.4287 (2)	0.4853 (2)	0.34947 (8)	0.0347 (5)
O36	0.6260 (3)	0.2179 (2)	0.31685 (9)	0.0405 (5)
O35	0.4564 (3)	−0.1119 (2)	0.23731 (9)	0.0486 (6)
O2	0.2147 (2)	0.2350 (2)	0.28185 (8)	0.0338 (5)
O34	0.1749 (3)	−0.2251 (2)	0.34014 (10)	0.0651 (7)
O37	0.7976 (3)	0.2882 (2)	0.22423 (9)	0.0497 (6)
O38	0.6095 (3)	−0.0340 (3)	0.13978 (10)	0.0721 (9)
O39	0.8640 (3)	0.0934 (3)	0.03546 (11)	0.0786 (8)
O33	0.3555 (3)	0.1049 (2)	0.41626 (9)	0.0514 (6)
O40	1.0599 (3)	0.4112 (2)	0.11841 (10)	0.0544 (6)
O51	0.3770 (3)	0.6075 (3)	0.17219 (13)	0.0548 (6)
O50	0.0523 (3)	0.4664 (2)	0.31318 (11)	0.0549 (6)
C27	0.6983 (4)	0.4927 (3)	0.06667 (12)	0.0338 (7)
C2	0.3118 (4)	0.5365 (3)	0.47539 (13)	0.0389 (7)
H2	0.3951	0.6012	0.4525	0.047*
C3	0.3094 (4)	0.5804 (4)	0.53658 (13)	0.0451 (8)
H3	0.3902	0.6723	0.5548	0.054*
C9	−0.2642 (4)	−0.0740 (4)	0.43114 (17)	0.0538 (9)
H9	−0.3534	−0.1522	0.4468	0.065*
H36	0.674 (5)	0.223 (4)	0.2865 (15)	0.081*
H38	0.564 (5)	−0.043 (4)	0.1711 (16)	0.081*
H51A	0.374 (5)	0.676 (3)	0.1883 (16)	0.081*
H51B	0.286 (3)	0.561 (4)	0.1635 (17)	0.081*
H50A	0.095 (5)	0.548 (2)	0.3122 (18)	0.081*
H50B	−0.004 (4)	0.434 (4)	0.2851 (11)	0.081*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C29	0.079 (3)	0.064 (2)	0.0269 (17)	0.031 (2)	0.0105 (18)	−0.0031 (17)
C28	0.055 (2)	0.055 (2)	0.0356 (18)	0.0194 (18)	0.0192 (16)	0.0083 (17)
C26	0.0335 (17)	0.0356 (17)	0.0354 (17)	0.0106 (14)	0.0105 (14)	0.0100 (14)
C5	0.0415 (19)	0.060 (2)	0.0292 (17)	0.0251 (17)	0.0138 (15)	0.0100 (16)
C4	0.050 (2)	0.065 (2)	0.0260 (16)	0.0289 (19)	0.0034 (15)	−0.0049 (16)
C33	0.0314 (16)	0.0359 (17)	0.0383 (18)	0.0092 (14)	0.0078 (14)	0.0052 (15)
C40	0.0318 (17)	0.0417 (19)	0.0411 (18)	0.0112 (15)	0.0063 (15)	0.0060 (16)
C23	0.048 (2)	0.047 (2)	0.070 (3)	−0.0007 (17)	0.0061 (19)	0.0035 (19)
C24	0.050 (2)	0.045 (2)	0.075 (3)	−0.0046 (17)	0.028 (2)	0.021 (2)
C25	0.054 (2)	0.052 (2)	0.052 (2)	0.0110 (18)	0.0238 (18)	0.0115 (18)
C11	0.0441 (19)	0.0362 (18)	0.0422 (18)	0.0122 (15)	0.0030 (15)	−0.0022 (15)
C31	0.057 (2)	0.0358 (18)	0.0340 (18)	0.0037 (16)	0.0069 (16)	−0.0012 (15)
C6	0.0266 (16)	0.0391 (17)	0.0315 (16)	0.0143 (14)	0.0083 (13)	0.0071 (14)
C37	0.0311 (16)	0.0310 (16)	0.0360 (17)	0.0045 (13)	0.0036 (14)	−0.0022 (14)
C10	0.0415 (19)	0.0324 (18)	0.066 (2)	0.0041 (15)	−0.0026 (17)	0.0016 (17)
C36	0.0327 (16)	0.0280 (16)	0.0339 (16)	0.0097 (13)	0.0044 (13)	0.0008 (13)
C7	0.0288 (16)	0.0392 (17)	0.0310 (16)	0.0128 (14)	0.0087 (13)	0.0082 (14)
C14	0.0325 (16)	0.0232 (15)	0.0291 (15)	0.0084 (13)	0.0057 (13)	0.0049 (12)
C39	0.060 (2)	0.0401 (19)	0.0400 (19)	0.0134 (17)	0.0189 (17)	0.0039 (16)
C34	0.0435 (19)	0.0319 (17)	0.0377 (17)	0.0076 (15)	0.0113 (15)	0.0028 (14)
C35	0.0392 (18)	0.0300 (16)	0.0353 (17)	0.0103 (14)	0.0074 (14)	0.0033 (13)
C38	0.0499 (19)	0.0357 (18)	0.0363 (17)	0.0051 (16)	0.0152 (15)	0.0027 (14)
C30	0.074 (2)	0.051 (2)	0.0324 (18)	0.0177 (19)	0.0008 (17)	−0.0110 (16)
C8	0.0356 (18)	0.047 (2)	0.049 (2)	0.0081 (15)	0.0152 (15)	0.0186 (17)
C22	0.049 (2)	0.0426 (19)	0.0416 (19)	−0.0023 (16)	0.0080 (16)	−0.0041 (16)
C13	0.0316 (16)	0.0293 (15)	0.0211 (14)	0.0072 (13)	0.0032 (12)	0.0022 (12)
Cu1	0.0355 (2)	0.0338 (2)	0.0270 (2)	0.00095 (17)	0.01112 (16)	−0.00281 (16)
Cu2	0.0445 (2)	0.0348 (2)	0.0263 (2)	−0.00346 (18)	0.01315 (17)	−0.00237 (17)
N32	0.0434 (15)	0.0290 (13)	0.0240 (12)	0.0060 (11)	0.0080 (11)	0.0003 (11)
N21	0.0365 (14)	0.0341 (14)	0.0318 (13)	0.0052 (12)	0.0120 (11)	0.0023 (11)
N12	0.0324 (13)	0.0271 (13)	0.0306 (13)	0.0054 (11)	0.0066 (11)	0.0020 (11)
N1	0.0290 (13)	0.0359 (14)	0.0296 (13)	0.0126 (11)	0.0085 (11)	0.0024 (11)
O4	0.0451 (12)	0.0323 (11)	0.0249 (10)	−0.0008 (9)	0.0127 (9)	−0.0029 (9)
O3	0.0356 (11)	0.0361 (11)	0.0283 (10)	−0.0045 (9)	0.0118 (9)	−0.0010 (9)
O1	0.0345 (11)	0.0397 (11)	0.0225 (10)	0.0009 (9)	0.0120 (8)	−0.0039 (9)
O36	0.0429 (13)	0.0322 (11)	0.0370 (12)	−0.0012 (10)	0.0124 (10)	−0.0047 (10)
O35	0.0613 (14)	0.0345 (12)	0.0430 (13)	0.0033 (10)	0.0227 (11)	−0.0059 (10)
O2	0.0356 (11)	0.0314 (11)	0.0278 (10)	0.0005 (9)	0.0123 (9)	−0.0020 (9)
O34	0.0750 (17)	0.0327 (12)	0.0725 (16)	−0.0079 (12)	0.0343 (14)	−0.0034 (12)
O37	0.0482 (13)	0.0467 (13)	0.0396 (12)	−0.0057 (11)	0.0172 (10)	−0.0095 (10)
O38	0.098 (2)	0.0419 (13)	0.0493 (15)	−0.0199 (13)	0.0406 (14)	−0.0093 (12)
O39	0.111 (2)	0.0521 (15)	0.0578 (16)	−0.0016 (15)	0.0491 (15)	−0.0086 (13)
O33	0.0592 (14)	0.0470 (13)	0.0398 (13)	0.0040 (11)	0.0216 (11)	−0.0087 (11)
O40	0.0439 (13)	0.0488 (14)	0.0559 (14)	−0.0056 (11)	0.0100 (11)	0.0072 (12)
O51	0.0473 (14)	0.0413 (15)	0.0677 (17)	0.0078 (12)	−0.0016 (13)	−0.0169 (12)
O50	0.0667 (18)	0.0347 (13)	0.0530 (15)	0.0093 (13)	−0.0159 (12)	−0.0043 (13)
C27	0.0435 (18)	0.0367 (17)	0.0276 (15)	0.0192 (15)	0.0119 (14)	0.0087 (14)
C2	0.0340 (17)	0.0376 (18)	0.0396 (18)	0.0042 (14)	0.0064 (14)	−0.0028 (15)
C3	0.0415 (19)	0.054 (2)	0.0396 (19)	0.0194 (16)	−0.0031 (15)	−0.0141 (16)
C9	0.041 (2)	0.039 (2)	0.077 (3)	0.0047 (16)	0.0101 (19)	0.0259 (19)

Geometric parameters (Å, º)

Cu1—N1	1.958 (2)	C23—C24	1.375 (4)
Cu1—N12	1.969 (2)	C23—H23	0.93
Cu1—O1	1.9775 (17)	C24—C25	1.358 (4)
Cu1—O2	1.9644 (17)	C24—H24	0.93
Cu1—O50	2.219 (3)	C25—H25	0.93
Cu2—N21	1.957 (2)	C11—N12	1.332 (3)
Cu2—N32	1.954 (2)	C11—C10	1.373 (4)
Cu2—O3	1.9746 (17)	C11—H11	0.93
Cu2—O4	1.9778 (17)	C31—N32	1.340 (3)
Cu2—O51	2.277 (3)	C31—C30	1.361 (4)
C33—O33	1.223 (3)	C31—H31	0.93
C33—C34	1.497 (4)	C6—N1	1.345 (3)
C34—O34	1.219 (3)	C6—C7	1.475 (4)
C34—C35	1.494 (4)	C10—C9	1.369 (4)
C35—O35	1.253 (3)	C10—H10	0.93
C35—C36	1.411 (4)	C7—N12	1.343 (3)
C36—O36	1.297 (3)	C7—C8	1.369 (3)
C36—C33	1.435 (4)	C14—O4	1.249 (3)
C37—O37	1.256 (3)	C14—O2	1.254 (3)
C37—C38	1.417 (4)	C14—C13	1.542 (3)
C38—O38	1.295 (3)	C30—H30	0.93
C38—C39	1.453 (4)	C8—C9	1.362 (4)
C39—O39	1.213 (3)	C8—H8	0.93
C39—C40	1.510 (4)	C22—N21	1.337 (3)
C40—O40	1.212 (3)	C22—H22	0.93
C40—C37	1.483 (4)	C13—O1	1.246 (3)
C29—C30	1.361 (4)	C13—O3	1.258 (3)
C29—C28	1.377 (4)	N32—C27	1.337 (3)
C29—H29	0.93	N1—C2	1.326 (3)
C28—C27	1.384 (4)	O36—H36	0.79 (3)
C28—H28	0.93	O38—H38	0.79 (3)
C26—N21	1.350 (3)	O51—H51A	0.722 (16)
C26—C25	1.379 (4)	O51—H51B	0.720 (16)
C26—C27	1.470 (4)	O50—H50A	0.723 (16)
C5—C4	1.377 (4)	O50—H50B	0.719 (16)
C5—C6	1.390 (3)	C2—C3	1.380 (3)
C5—H5	0.93	C2—H2	0.93
C4—C3	1.373 (4)	C3—H3	0.93
C4—H4	0.93	C9—H9	0.93
C23—C22	1.374 (4)
N1—Cu1—N12	82.36 (9)	O4—C14—O2	125.7 (3)
N1—Cu1—O2	171.31 (8)	O4—C14—C13	117.2 (2)
N1—Cu1—O50	99.90 (9)	O2—C14—C13	117.1 (2)
N12—Cu1—O1	168.28 (8)	O39—C39—C38	137.1 (3)
N12—Cu1—O50	100.62 (9)	O39—C39—C40	135.4 (3)
O1—Cu1—O2	85.40 (7)	C38—C39—C40	87.5 (2)
O1—Cu1—O50	91.04 (9)	O34—C34—C35	136.6 (3)
O2—Cu1—O50	88.79 (9)	O34—C34—C33	134.9 (3)
N21—Cu2—N32	82.50 (9)	C35—C34—C33	88.5 (2)
N21—Cu2—O4	171.87 (9)	O35—C35—C36	136.2 (3)
N21—Cu2—O51	99.52 (9)	O35—C35—C34	134.7 (3)
N32—Cu2—O3	174.38 (9)	C36—C35—C34	89.1 (2)
N32—Cu2—O51	99.76 (9)	O38—C38—C37	136.5 (3)
O3—Cu2—O4	85.50 (7)	O38—C38—C39	129.7 (3)
O3—Cu2—O51	85.84 (9)	C37—C38—C39	93.7 (2)
O4—Cu2—O51	88.33 (8)	C31—C30—C29	118.8 (3)
C30—C29—C28	119.7 (3)	C31—C30—H30	120.6
C30—C29—H29	120.1	C29—C30—H30	120.6
C28—C29—H29	120.1	C9—C8—C7	119.5 (3)
C29—C28—C27	119.0 (3)	C9—C8—H8	120.2
C29—C28—H28	120.5	C7—C8—H8	120.2
C27—C28—H28	120.5	N21—C22—C23	122.7 (3)
N21—C26—C25	121.0 (3)	N21—C22—H22	118.7
N21—C26—C27	114.3 (2)	C23—C22—H22	118.7
C25—C26—C27	124.7 (3)	O1—C13—O3	126.3 (3)
C4—C5—C6	119.8 (3)	O1—C13—C14	116.7 (2)
C4—C5—H5	120.1	O3—C13—C14	117.0 (2)
C6—C5—H5	120.1	O2—Cu1—N12	95.98 (8)
C3—C4—C5	119.4 (3)	N1—Cu1—O1	94.52 (8)
C3—C4—H4	120.3	N21—Cu2—O3	97.13 (8)
C5—C4—H4	120.3	N32—Cu2—O4	94.12 (8)
O33—C33—C36	136.5 (3)	C27—N32—C31	119.3 (2)
O33—C33—C34	135.4 (3)	C27—N32—Cu2	114.65 (18)
C36—C33—C34	88.1 (2)	C31—N32—Cu2	126.04 (19)
O40—C40—C37	136.4 (3)	C22—N21—C26	118.8 (2)
O40—C40—C39	134.8 (3)	C22—N21—Cu2	127.02 (19)
C37—C40—C39	88.8 (2)	C26—N21—Cu2	114.01 (19)
C22—C23—C24	117.8 (3)	C11—N12—C7	118.5 (2)
C22—C23—H23	121.1	C11—N12—Cu1	126.94 (19)
C24—C23—H23	121.1	C7—N12—Cu1	114.46 (18)
C25—C24—C23	120.5 (3)	C2—N1—C6	119.9 (2)
C25—C24—H24	119.8	C2—N1—Cu1	125.74 (19)
C23—C24—H24	119.8	C6—N1—Cu1	114.40 (18)
C24—C25—C26	119.3 (3)	C14—O4—Cu2	109.20 (17)
C24—C25—H25	120.4	C13—O3—Cu2	109.00 (16)
C26—C25—H25	120.4	C13—O1—Cu1	110.15 (17)
N12—C11—C10	122.8 (3)	C36—O36—H36	115 (3)
N12—C11—H11	118.6	C14—O2—Cu1	109.92 (16)
C10—C11—H11	118.6	C38—O38—H38	116 (3)
N32—C31—C30	122.4 (3)	Cu2—O51—H51A	131 (3)
N32—C31—H31	118.8	Cu2—O51—H51B	117 (3)
C30—C31—H31	118.8	H51A—O51—H51B	106 (4)
N1—C6—C5	120.0 (3)	Cu1—O50—H50A	119 (3)
N1—C6—C7	114.7 (2)	Cu1—O50—H50B	120 (3)
C5—C6—C7	125.3 (3)	H50A—O50—H50B	111 (4)
O37—C37—C38	136.3 (3)	N32—C27—C28	120.7 (3)
O37—C37—C40	133.7 (3)	N32—C27—C26	114.3 (2)
C38—C37—C40	89.9 (2)	C28—C27—C26	124.9 (3)
C11—C10—C9	118.1 (3)	N1—C2—C3	122.7 (3)
C11—C10—H10	121	N1—C2—H2	118.6
C9—C10—H10	121	C3—C2—H2	118.6
O36—C36—C35	136.3 (3)	C4—C3—C2	118.3 (3)
O36—C36—C33	129.4 (3)	C4—C3—H3	120.9
C35—C36—C33	94.3 (2)	C2—C3—H3	120.9
N12—C7—C8	121.3 (3)	C8—C9—C10	119.7 (3)
N12—C7—C6	114.1 (2)	C8—C9—H9	120.1
C8—C7—C6	124.5 (3)	C10—C9—H9	120.1
C30—C29—C28—C27	0.0 (5)	N32—Cu2—N21—C22	178.6 (3)
C6—C5—C4—C3	0.5 (4)	O3—Cu2—N21—C22	−7.0 (3)
C22—C23—C24—C25	−1.1 (5)	O51—Cu2—N21—C22	79.9 (3)
C23—C24—C25—C26	0.4 (5)	N32—Cu2—N21—C26	3.26 (19)
N21—C26—C25—C24	0.5 (5)	O3—Cu2—N21—C26	177.60 (19)
C27—C26—C25—C24	−179.4 (3)	O51—Cu2—N21—C26	−95.4 (2)
C4—C5—C6—N1	−0.1 (4)	C10—C11—N12—C7	0.8 (4)
C4—C5—C6—C7	178.4 (3)	C10—C11—N12—Cu1	176.5 (2)
O40—C40—C37—O37	2.5 (6)	C8—C7—N12—C11	−2.6 (4)
C39—C40—C37—O37	−175.8 (3)	C6—C7—N12—C11	177.4 (2)
O40—C40—C37—C38	179.0 (4)	C8—C7—N12—Cu1	−178.8 (2)
C39—C40—C37—C38	0.7 (2)	C6—C7—N12—Cu1	1.2 (3)
N12—C11—C10—C9	0.6 (5)	N1—Cu1—N12—C11	−176.9 (2)
O33—C33—C36—O36	−0.1 (6)	O2—Cu1—N12—C11	−5.5 (2)
C34—C33—C36—O36	179.6 (3)	O1—Cu1—N12—C11	−101.7 (4)
O33—C33—C36—C35	−179.6 (4)	O50—Cu1—N12—C11	84.4 (2)
C34—C33—C36—C35	0.2 (2)	N1—Cu1—N12—C7	−1.03 (18)
N1—C6—C7—N12	−0.6 (3)	O2—Cu1—N12—C7	170.38 (18)
C5—C6—C7—N12	−179.2 (2)	O1—Cu1—N12—C7	74.2 (4)
N1—C6—C7—C8	179.3 (3)	O50—Cu1—N12—C7	−99.73 (19)
C5—C6—C7—C8	0.8 (4)	C5—C6—N1—C2	−0.7 (4)
O40—C40—C39—O39	0.1 (7)	C7—C6—N1—C2	−179.4 (2)
C37—C40—C39—O39	178.4 (4)	C5—C6—N1—Cu1	178.43 (19)
O40—C40—C39—C38	−179.1 (4)	C7—C6—N1—Cu1	−0.2 (3)
C37—C40—C39—C38	−0.7 (2)	N12—Cu1—N1—C2	179.7 (2)
O33—C33—C34—O34	2.8 (6)	O1—Cu1—N1—C2	11.1 (2)
C36—C33—C34—O34	−177.0 (4)	O50—Cu1—N1—C2	−80.7 (2)
O33—C33—C34—C35	179.6 (3)	N12—Cu1—N1—C6	0.66 (18)
C36—C33—C34—C35	−0.2 (2)	O1—Cu1—N1—C6	−167.97 (18)
O36—C36—C35—O35	0.0 (6)	O50—Cu1—N1—C6	100.18 (18)
C33—C36—C35—O35	179.3 (3)	O2—C14—O4—Cu2	171.8 (2)
O36—C36—C35—C34	−179.5 (3)	C13—C14—O4—Cu2	−9.4 (3)
C33—C36—C35—C34	−0.2 (2)	N32—Cu2—O4—C14	−173.49 (17)
O34—C34—C35—O35	−2.7 (6)	O3—Cu2—O4—C14	12.13 (17)
C33—C34—C35—O35	−179.4 (3)	O51—Cu2—O4—C14	−73.82 (18)
O34—C34—C35—C36	176.9 (4)	O1—C13—O3—Cu2	−169.7 (2)
C33—C34—C35—C36	0.2 (2)	C14—C13—O3—Cu2	11.1 (3)
O37—C37—C38—O38	−1.7 (7)	N21—Cu2—O3—C13	174.98 (17)
C40—C37—C38—O38	−178.1 (4)	O4—Cu2—O3—C13	−12.75 (18)
O37—C37—C38—C39	175.6 (4)	O51—Cu2—O3—C13	75.89 (18)
C40—C37—C38—C39	−0.8 (2)	O3—C13—O1—Cu1	176.0 (2)
O39—C39—C38—O38	−0.8 (7)	C14—C13—O1—Cu1	−4.8 (3)
C40—C39—C38—O38	178.4 (4)	N1—Cu1—O1—C13	178.07 (18)
O39—C39—C38—C37	−178.4 (4)	O2—Cu1—O1—C13	6.79 (17)
C40—C39—C38—C37	0.7 (2)	N12—Cu1—O1—C13	104.1 (4)
N32—C31—C30—C29	−1.1 (5)	O50—Cu1—O1—C13	−81.92 (18)
C28—C29—C30—C31	0.4 (5)	O4—C14—O2—Cu1	−174.1 (2)
N12—C7—C8—C9	2.8 (4)	C13—C14—O2—Cu1	7.1 (3)
C6—C7—C8—C9	−177.2 (3)	N12—Cu1—O2—C14	−175.93 (18)
C24—C23—C22—N21	0.9 (5)	O1—Cu1—O2—C14	−7.62 (17)
O4—C14—C13—O1	179.5 (2)	O50—Cu1—O2—C14	83.52 (18)
O2—C14—C13—O1	−1.6 (4)	C31—N32—C27—C28	−0.8 (4)
O4—C14—C13—O3	−1.2 (4)	Cu2—N32—C27—C28	177.5 (2)
O2—C14—C13—O3	177.7 (2)	C31—N32—C27—C26	180.0 (3)
C30—C31—N32—C27	1.3 (4)	Cu2—N32—C27—C26	−1.7 (3)
C30—C31—N32—Cu2	−176.8 (2)	C29—C28—C27—N32	0.2 (4)
N21—Cu2—N32—C27	−0.73 (19)	C29—C28—C27—C26	179.3 (3)
O4—Cu2—N32—C27	−173.30 (19)	N21—C26—C27—N32	4.5 (3)
O51—Cu2—N32—C27	97.70 (19)	C25—C26—C27—N32	−175.7 (3)
N21—Cu2—N32—C31	177.4 (3)	N21—C26—C27—C28	−174.7 (3)
O4—Cu2—N32—C31	4.9 (2)	C25—C26—C27—C28	5.1 (5)
O51—Cu2—N32—C31	−84.1 (2)	C6—N1—C2—C3	1.1 (4)
C23—C22—N21—C26	0.0 (4)	Cu1—N1—C2—C3	−177.9 (2)
C23—C22—N21—Cu2	−175.2 (2)	C5—C4—C3—C2	−0.2 (4)
C25—C26—N21—C22	−0.7 (4)	N1—C2—C3—C4	−0.6 (4)
C27—C26—N21—C22	179.2 (3)	C7—C8—C9—C10	−1.3 (5)
C25—C26—N21—Cu2	175.1 (2)	C11—C10—C9—C8	−0.4 (5)
C27—C26—N21—Cu2	−5.0 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O36—H36···O37	0.79 (4)	1.75 (4)	2.517 (3)	164 (4)
O38—H38···O35	0.79 (4)	1.77 (4)	2.546 (3)	166 (4)
O50—H50A···O34^i	0.72 (2)	2.03 (2)	2.711 (3)	158 (4)
O50—H50B···O37^ii	0.72 (3)	2.05 (3)	2.737 (3)	161 (4)
O51—H51A···O35^i	0.72 (3)	2.07 (3)	2.758 (3)	161 (4)
O51—H51B···O40^ii	0.72 (3)	2.03 (3)	2.722 (3)	164 (4)
C2—H2···O1	0.93	2.52	3.037 (3)	115
C3—H3···O33^iii	0.93	2.39	3.296 (4)	166
C5—H5···O34^iv	0.93	2.52	3.360 (4)	151
C8—H8···O33^iv	0.93	2.47	3.198 (4)	136
C25—H25···O39^v	0.93	2.42	3.153 (4)	136
C30—H30···O39^vi	0.93	2.37	3.284 (4)	169
C31—H31···O4	0.93	2.50	3.021 (3)	116

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