Octa­ammonium diaqua­hexa-μ₂-oxalato-dioxalatotetra­copper(II) tetra­hydrate

In the structure of the title compound, (NH₄)₈[Cu₄(C₂O₄)₈(H₂O)₂]·4H₂O, isolated tetra­mers of [Cu(ox)₂]²⁺ (ox is oxalate) are present. Each Cu^II ion coordinates to four O atoms in two oxalate ligands and to two more distant O atoms in a neighbouring oxalate ligand or a water mol­ecule. An extensive hydrogen-bonding network connects the tetra­mers to two unique solvent water mol­ecules and four ammonium ions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.032
• wR factor = 0.061
• Data-to-parameter ratio = 16.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Cu2    -   O17     ..      14.03 su

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O6     -   C3      ..       5.06 su
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C1     -   C2     ...       1.55 Ang.
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C3     -   C4     ...       1.55 Ang.
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C5     -   C6     ...       1.54 Ang.
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C7     -   C8     ...       1.56 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H22    ..  O16     ..       2.63 Ang.
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          1
            O8  -CU1 -O1  -C1     58.10  1.60   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          6
            O5  -CU1 -O4  -C2    140.30  1.90   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          9
            O4  -CU1 -O5  -C3     39.00  2.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         10
            O1  -CU1 -O8  -C4    124.70  1.50   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         14
            O16 -CU2 -O9  -C5    106.30  0.90   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         18
            O13 -CU2 -O12 -C6    -84.40  0.80   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         19
            O12 -CU2 -O13 -C7   -106.50  0.80   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         23
            O9  -CU2 -O16 -C8     78.20  0.90   1.555   1.555   1.555   1.555
PLAT732_ALERT_1_C Angle   Calc      104(4), Rep   103.5(17) ......       2.35 su-Rat
              H191 -O19  -H192    1.555   1.555   1.555
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          6
              H2 O

Alert level G
FORMU01_ALERT_1_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and _chemical_formula_moiety. This is
            usually due to the moiety formula being in the wrong format.
            Atom count from _chemical_formula_sum:   C16 H44 Cu4 N8 O38
            Atom count from _chemical_formula_moiety:C16 H52 Cu4 O38
ABSTM02_ALERT_3_G  The ratio of expected to reported Tmax/Tmin(RR) is > 1.10
            Tmin and Tmax reported:      0.630     0.790
            Tmin and Tmax expected:      0.603     0.898
            RR =      1.186
            Please check that your absorption correction is appropriate.

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

   5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 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
  10 ALERT type 4 Improvement, methodology, query or suggestion

---

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: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Bergerhoff, 1996); software used to prepare material for publication: PLATON (Spek, 2003) and SHELXL97.

Octaammonium diaquahexa-µ₂-oxalato-dioxalatotetracopper(II) tetrahydrate

Crystal data

(NH4)8[Cu4(C2O4)8(H2O)2]·4H2O	F(000) = 1232
Mr = 1210.76	Dx = 1.944 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 44987 reflections
a = 11.1364 (6) Å	θ = 1.0–33.4°
b = 11.2806 (6) Å	µ = 2.16 mm^−1
c = 17.1470 (12) Å	T = 293 K
β = 106.235 (5)°	Plate, light_blue
V = 2068.2 (2) Å^3	0.50 × 0.20 × 0.05 mm
Z = 2

Data collection

Oxford Xcalibur-3 κ- diffractometer with Sapphire-III CCD detector	6003 independent reflections
Radiation source: fine-focus sealed tube	2994 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.067
Detector resolution: 12 pixels mm^-1	θmax = 30.0°, θmin = 3.8°
ω scans at different φ	h = −15→15
Absorption correction: numerical (X-RED; Stoe & Cie, 1997)	k = −15→15
Tmin = 0.63, Tmax = 0.79	l = −24→24
37577 measured reflections

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)] = 0.033	Hydrogen site location: difference Fourier map
wR(F^2) = 0.061	Only H-atom coordinates refined
S = 0.84	w = 1/[σ^2(Fo^2) + (0.0199P)^2] where P = (Fo^2 + 2Fc^2)/3
6003 reflections	(Δ/σ)max = 0.001
366 parameters	Δρmax = 0.40 e Å^−3
49 restraints	Δρmin = −0.36 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
Cu1	0.40803 (3)	0.41798 (3)	0.41453 (2)	0.02631 (10)
Cu2	0.07726 (3)	0.37175 (3)	0.35794 (2)	0.02753 (10)
O1	0.43841 (16)	0.26045 (15)	0.38414 (10)	0.0292 (4)
O2	0.41019 (18)	0.07420 (17)	0.41938 (11)	0.0374 (5)
O3	0.28188 (16)	0.16242 (15)	0.52262 (11)	0.0336 (5)
O4	0.31815 (15)	0.34460 (16)	0.48334 (10)	0.0267 (4)
O5	0.49268 (16)	0.49588 (16)	0.34431 (10)	0.0296 (5)
O6	0.51588 (16)	0.67863 (16)	0.30121 (11)	0.0349 (5)
O7	0.41022 (16)	0.76258 (15)	0.41640 (10)	0.0288 (4)
O8	0.38175 (15)	0.57528 (15)	0.45030 (10)	0.0255 (4)
O9	0.11539 (15)	0.21517 (15)	0.32515 (10)	0.0269 (4)
O10	0.07831 (16)	0.02648 (16)	0.35055 (11)	0.0325 (5)
O11	−0.05758 (16)	0.10621 (16)	0.45064 (11)	0.0339 (5)
O12	−0.00105 (15)	0.29047 (16)	0.42988 (10)	0.0281 (4)
O13	0.17223 (16)	0.45002 (16)	0.29365 (10)	0.0279 (4)
O14	0.20329 (16)	0.63328 (16)	0.25489 (11)	0.0339 (5)
O15	0.08867 (16)	0.71733 (17)	0.36737 (12)	0.0380 (5)
O16	0.05399 (16)	0.52916 (15)	0.39616 (10)	0.0282 (4)
C1	0.3978 (2)	0.1807 (3)	0.42437 (16)	0.0239 (6)
C2	0.3260 (2)	0.2312 (2)	0.48273 (15)	0.0228 (6)
C3	0.4811 (2)	0.6090 (2)	0.34496 (16)	0.0240 (6)
C4	0.4184 (2)	0.6553 (3)	0.40898 (16)	0.0216 (6)
C5	0.0694 (2)	0.1333 (3)	0.36031 (15)	0.0211 (6)
C6	−0.0041 (2)	0.1783 (3)	0.41861 (15)	0.0237 (6)
C7	0.1627 (2)	0.5634 (3)	0.29584 (16)	0.0238 (6)
C8	0.0957 (2)	0.6102 (3)	0.35851 (16)	0.0255 (7)
O17	−0.1406 (2)	0.38073 (18)	0.25935 (12)	0.0414 (6)
H171	−0.142 (3)	0.3242 (15)	0.2384 (16)	0.062*
H172	−0.131 (3)	0.4251 (19)	0.2295 (15)	0.062*
N1	0.11360 (19)	0.36813 (19)	0.12100 (13)	0.0319 (6)
H11	0.0578 (15)	0.3114 (14)	0.1168 (12)	0.048*
H12	0.0788 (17)	0.4298 (12)	0.0939 (11)	0.048*
H13	0.1471 (17)	0.3848 (17)	0.1719 (6)	0.048*
H14	0.1714 (15)	0.3415 (17)	0.0992 (11)	0.048*
O18	0.23648 (19)	1.1407 (2)	0.20398 (12)	0.0480 (6)
H181	0.214 (3)	1.148 (3)	0.2395 (14)	0.072*
H182	0.3029 (16)	1.157 (3)	0.2166 (18)	0.072*
N2	0.2001 (2)	0.9684 (2)	0.07376 (14)	0.0419 (7)
H21	0.1333 (13)	0.9505 (19)	0.0365 (10)	0.063*
H22	0.185 (2)	1.0101 (17)	0.1130 (10)	0.063*
H23	0.2422 (18)	0.9049 (13)	0.0942 (12)	0.063*
H24	0.2491 (17)	1.0119 (17)	0.0527 (12)	0.063*
O19	0.31953 (19)	0.7411 (2)	0.13825 (14)	0.0494 (6)
H191	0.3872 (14)	0.734 (3)	0.1467 (19)	0.074*
H192	0.303 (3)	0.702 (3)	0.1683 (18)	0.074*
N3	0.5835 (2)	0.42278 (19)	0.21013 (13)	0.0369 (6)
H31	0.5661 (19)	0.4744 (15)	0.1699 (10)	0.055*
H32	0.5538 (19)	0.4488 (18)	0.2484 (10)	0.055*
H33	0.6656 (9)	0.4164 (19)	0.2282 (12)	0.055*
H34	0.5521 (18)	0.3545 (11)	0.1920 (12)	0.055*
N4	0.2672 (2)	0.59639 (19)	−0.01195 (14)	0.0376 (6)
H41	0.1925 (11)	0.5846 (18)	−0.0438 (11)	0.056*
H42	0.263 (2)	0.6267 (18)	0.0341 (8)	0.056*
H43	0.3095 (17)	0.5313 (12)	−0.0036 (12)	0.056*
H44	0.3052 (18)	0.6487 (15)	−0.0352 (12)	0.056*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.03291 (19)	0.0217 (2)	0.0301 (2)	−0.00016 (16)	0.01826 (16)	0.00014 (16)
Cu2	0.0356 (2)	0.0214 (2)	0.0313 (2)	−0.00111 (16)	0.01861 (16)	−0.00058 (16)
O1	0.0395 (11)	0.0217 (11)	0.0345 (11)	−0.0001 (9)	0.0235 (9)	−0.0011 (9)
O2	0.0577 (13)	0.0178 (12)	0.0454 (13)	0.0017 (11)	0.0284 (10)	−0.0013 (10)
O3	0.0423 (11)	0.0272 (12)	0.0406 (12)	−0.0050 (9)	0.0267 (10)	0.0037 (10)
O4	0.0319 (11)	0.0209 (12)	0.0326 (11)	−0.0009 (8)	0.0176 (9)	−0.0020 (9)
O5	0.0440 (12)	0.0192 (11)	0.0349 (12)	0.0017 (9)	0.0265 (10)	0.0003 (9)
O6	0.0454 (12)	0.0282 (12)	0.0405 (12)	0.0034 (9)	0.0275 (10)	0.0124 (10)
O7	0.0400 (11)	0.0173 (12)	0.0338 (12)	0.0033 (9)	0.0183 (9)	0.0001 (9)
O8	0.0338 (10)	0.0197 (11)	0.0283 (11)	0.0012 (9)	0.0172 (9)	0.0020 (9)
O9	0.0334 (10)	0.0215 (11)	0.0310 (11)	−0.0017 (8)	0.0174 (9)	0.0003 (9)
O10	0.0387 (11)	0.0183 (12)	0.0451 (13)	−0.0011 (9)	0.0192 (10)	−0.0037 (10)
O11	0.0422 (12)	0.0275 (12)	0.0393 (12)	−0.0044 (9)	0.0235 (10)	0.0035 (9)
O12	0.0374 (11)	0.0220 (11)	0.0312 (11)	0.0027 (9)	0.0198 (9)	0.0012 (9)
O13	0.0344 (11)	0.0222 (11)	0.0323 (11)	−0.0017 (9)	0.0181 (9)	0.0000 (9)
O14	0.0404 (11)	0.0301 (12)	0.0339 (12)	−0.0029 (10)	0.0151 (10)	0.0078 (10)
O15	0.0448 (12)	0.0203 (12)	0.0544 (14)	0.0007 (10)	0.0230 (11)	−0.0037 (10)
O16	0.0358 (11)	0.0224 (11)	0.0319 (12)	−0.0007 (9)	0.0186 (9)	−0.0003 (9)
C1	0.0251 (15)	0.0231 (18)	0.0243 (16)	−0.0021 (13)	0.0084 (13)	−0.0025 (14)
C2	0.0222 (15)	0.0249 (19)	0.0225 (15)	−0.0028 (13)	0.0079 (12)	−0.0011 (13)
C3	0.0215 (14)	0.0261 (19)	0.0243 (16)	0.0027 (12)	0.0062 (12)	0.0013 (13)
C4	0.0189 (14)	0.0210 (17)	0.0233 (16)	0.0015 (12)	0.0029 (12)	0.0000 (13)
C5	0.0180 (13)	0.0254 (18)	0.0191 (14)	0.0002 (13)	0.0041 (11)	0.0010 (14)
C6	0.0257 (15)	0.0234 (18)	0.0213 (16)	0.0031 (13)	0.0055 (12)	0.0034 (13)
C7	0.0199 (14)	0.0259 (18)	0.0229 (16)	−0.0017 (13)	0.0018 (12)	0.0025 (14)
C8	0.0198 (15)	0.027 (2)	0.0266 (16)	0.0011 (13)	0.0020 (12)	−0.0012 (14)
O17	0.0618 (14)	0.0262 (12)	0.0388 (13)	−0.0047 (13)	0.0185 (12)	−0.0007 (10)
N1	0.0355 (13)	0.0307 (14)	0.0336 (14)	0.0070 (11)	0.0164 (11)	0.0016 (12)
O18	0.0420 (13)	0.0593 (16)	0.0491 (15)	−0.0021 (13)	0.0234 (11)	−0.0075 (13)
N2	0.0379 (15)	0.0567 (18)	0.0352 (15)	−0.0056 (13)	0.0172 (13)	0.0038 (13)
O19	0.0382 (12)	0.0708 (18)	0.0418 (15)	−0.0038 (13)	0.0156 (11)	0.0005 (12)
N3	0.0547 (16)	0.0268 (14)	0.0361 (15)	−0.0026 (13)	0.0242 (13)	−0.0041 (12)
N4	0.0417 (15)	0.0297 (15)	0.0483 (17)	−0.0014 (12)	0.0240 (13)	−0.0035 (13)

Geometric parameters (Å, º)

Cu1—O1	1.9085 (17)	O16—C8	1.279 (3)
Cu1—O8	1.9262 (17)	C1—C2	1.554 (3)
Cu1—O4	1.9338 (17)	C3—C4	1.547 (3)
Cu1—O5	1.9353 (17)	C5—C6	1.545 (3)
Cu1—O8^i	2.7971 (17)	C7—C8	1.562 (4)
Cu1—O13	2.8779 (18)	O17—H171	0.730 (14)
Cu2—O12	1.9300 (17)	O17—H172	0.744 (15)
Cu2—O16	1.9348 (17)	N1—H11	0.880 (9)
Cu2—O9	1.9365 (17)	N1—H12	0.866 (9)
Cu2—O13	1.9403 (17)	N1—H13	0.868 (9)
Cu2—O17	2.542 (2)	N1—H14	0.882 (10)
Cu2—O4	2.9481 (17)	O18—H181	0.725 (15)
O1—C1	1.290 (3)	O18—H182	0.733 (15)
O2—C1	1.215 (3)	N2—H21	0.858 (10)
O3—C2	1.224 (3)	N2—H22	0.877 (10)
O4—C2	1.283 (3)	N2—H23	0.874 (10)
O5—C3	1.284 (3)	N2—H24	0.882 (10)
O6—C3	1.221 (3)	O19—H191	0.731 (15)
O7—C4	1.223 (3)	O19—H192	0.739 (15)
O8—C4	1.283 (3)	N3—H31	0.882 (10)
O9—C5	1.285 (3)	N3—H32	0.865 (10)
O10—C5	1.225 (3)	N3—H33	0.882 (10)
O11—C6	1.225 (3)	N3—H34	0.867 (10)
O12—C6	1.278 (3)	N4—H41	0.868 (9)
O13—C7	1.285 (3)	N4—H42	0.874 (10)
O14—C7	1.223 (3)	N4—H43	0.863 (10)
O15—C8	1.223 (3)	N4—H44	0.883 (10)
O1—Cu1—O8	177.34 (8)	O11—C6—C5	118.9 (2)
O1—Cu1—O4	85.96 (7)	O12—C6—C5	115.2 (2)
O8—Cu1—O4	92.83 (7)	O14—C7—O13	125.3 (2)
O1—Cu1—O5	95.65 (7)	O14—C7—C8	120.1 (3)
O8—Cu1—O5	85.62 (7)	O13—C7—C8	114.6 (2)
O4—Cu1—O5	177.74 (8)	O15—C8—O16	126.8 (3)
O12—Cu2—O16	95.29 (7)	O15—C8—C7	118.6 (3)
O12—Cu2—O9	85.82 (7)	O16—C8—C7	114.6 (2)
O16—Cu2—O9	175.08 (7)	H171—O17—H172	103.5 (17)
O12—Cu2—O13	174.14 (7)	H11—N1—H12	109.9 (12)
O16—Cu2—O13	85.46 (7)	H11—N1—H13	109.5 (12)
O9—Cu2—O13	92.95 (7)	H12—N1—H13	111.5 (12)
C1—O1—Cu1	112.83 (16)	H11—N1—H14	107.5 (12)
C2—O4—Cu1	111.96 (15)	H12—N1—H14	108.5 (12)
C3—O5—Cu1	112.24 (15)	H13—N1—H14	109.8 (12)
C4—O8—Cu1	111.88 (16)	H181—O18—H182	106.3 (18)
C5—O9—Cu2	111.76 (17)	H21—N2—H22	112.4 (13)
C6—O12—Cu2	111.80 (16)	H21—N2—H23	111.3 (13)
C7—O13—Cu2	111.94 (16)	H22—N2—H23	109.2 (12)
C8—O16—Cu2	112.53 (17)	H21—N2—H24	109.4 (12)
O2—C1—O1	126.1 (2)	H22—N2—H24	107.0 (12)
O2—C1—C2	119.8 (2)	H23—N2—H24	107.3 (12)
O1—C1—C2	114.2 (2)	H191—O19—H192	103.5 (17)
O3—C2—O4	126.1 (2)	H31—N3—H32	108.8 (12)
O3—C2—C1	119.1 (2)	H31—N3—H33	108.1 (12)
O4—C2—C1	114.8 (2)	H32—N3—H33	109.9 (12)
O6—C3—O5	125.7 (2)	H31—N3—H34	109.1 (12)
O6—C3—C4	120.2 (2)	H32—N3—H34	111.9 (13)
O5—C3—C4	114.1 (2)	H33—N3—H34	109.0 (12)
O7—C4—O8	126.5 (2)	H41—N4—H42	109.8 (12)
O7—C4—C3	118.0 (2)	H41—N4—H43	111.0 (13)
O8—C4—C3	115.5 (2)	H42—N4—H43	110.5 (12)
O10—C5—O9	125.8 (2)	H41—N4—H44	108.2 (12)
O10—C5—C6	119.3 (2)	H42—N4—H44	107.6 (12)
O9—C5—C6	114.9 (2)	H43—N4—H44	109.7 (12)
O11—C6—O12	125.8 (2)
O8—Cu1—O1—C1	58.1 (16)	O2—C1—C2—O3	−0.5 (4)
O4—Cu1—O1—C1	−4.89 (17)	O1—C1—C2—O3	178.7 (2)
O5—Cu1—O1—C1	176.69 (17)	O2—C1—C2—O4	−179.9 (2)
O1—Cu1—O4—C2	4.48 (16)	O1—C1—C2—O4	−0.7 (3)
O8—Cu1—O4—C2	−173.15 (16)	Cu1—O5—C3—O6	−173.4 (2)
O5—Cu1—O4—C2	140.3 (19)	Cu1—O5—C3—C4	7.5 (2)
O1—Cu1—O5—C3	174.69 (16)	Cu1—O8—C4—O7	177.8 (2)
O8—Cu1—O5—C3	−7.65 (16)	Cu1—O8—C4—C3	−3.5 (2)
O4—Cu1—O5—C3	39 (2)	O6—C3—C4—O7	−3.1 (4)
O1—Cu1—O8—C4	124.7 (15)	O5—C3—C4—O7	176.1 (2)
O4—Cu1—O8—C4	−172.38 (16)	O6—C3—C4—O8	178.0 (2)
O5—Cu1—O8—C4	5.97 (16)	O5—C3—C4—O8	−2.8 (3)
O12—Cu2—O9—C5	3.06 (16)	Cu2—O9—C5—O10	179.5 (2)
O16—Cu2—O9—C5	106.3 (9)	Cu2—O9—C5—C6	0.3 (3)
O13—Cu2—O9—C5	177.32 (16)	Cu2—O12—C6—O11	−173.4 (2)
O16—Cu2—O12—C6	178.47 (16)	Cu2—O12—C6—C5	7.9 (3)
O9—Cu2—O12—C6	−6.33 (16)	O10—C5—C6—O11	−3.8 (4)
O13—Cu2—O12—C6	−84.4 (8)	O9—C5—C6—O11	175.5 (2)
O12—Cu2—O13—C7	−106.5 (8)	O10—C5—C6—O12	175.0 (2)
O16—Cu2—O13—C7	−8.81 (16)	O9—C5—C6—O12	−5.7 (3)
O9—Cu2—O13—C7	175.85 (16)	Cu2—O13—C7—O14	−172.8 (2)
O12—Cu2—O16—C8	−178.91 (16)	Cu2—O13—C7—C8	8.7 (2)
O9—Cu2—O16—C8	78.2 (9)	Cu2—O16—C8—O15	176.5 (2)
O13—Cu2—O16—C8	6.93 (16)	Cu2—O16—C8—C7	−4.0 (2)
Cu1—O1—C1—O2	−176.5 (2)	O14—C7—C8—O15	−2.4 (4)
Cu1—O1—C1—C2	4.3 (3)	O13—C7—C8—O15	176.2 (2)
Cu1—O4—C2—O3	177.4 (2)	O14—C7—C8—O16	178.1 (2)
Cu1—O4—C2—C1	−3.3 (3)	O13—C7—C8—O16	−3.3 (3)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O17—H171···O14^ii	0.73 (2)	2.27 (2)	2.870 (3)	140 (2)
O17—H171···O15^ii	0.73 (2)	2.38 (2)	3.025 (3)	147 (2)
O17—H172···O10^iii	0.74 (2)	2.00 (2)	2.733 (3)	169 (2)
N1—H11···O15^ii	0.88 (2)	2.03 (2)	2.873 (3)	161 (2)
N1—H12···O11^iii	0.87 (2)	2.12 (2)	2.948 (3)	159 (2)
N1—H12···O10^iii	0.87 (2)	2.47 (2)	2.930 (3)	114 (2)
N1—H12···O11^iv	0.87 (2)	2.54 (2)	3.023 (3)	117 (2)
N1—H13···O13	0.87 (2)	2.16 (2)	2.993 (3)	162 (2)
N1—H14···O3^iv	0.88 (2)	2.04 (2)	2.871 (3)	158 (2)
O18—H181···O9^v	0.72 (2)	2.20 (2)	2.900 (3)	162 (2)
O18—H182···O6^vi	0.73 (2)	2.14 (2)	2.816 (3)	154 (2)
N2—H21···O16^vii	0.86 (2)	2.33 (2)	3.025 (3)	138 (2)
N2—H21···O12^iii	0.86 (2)	2.50 (2)	2.977 (3)	116 (2)
N2—H22···O18	0.88 (2)	2.10 (2)	2.901 (3)	151 (2)
N2—H22···O16^iii	0.88 (2)	2.63 (2)	3.093 (3)	114 (2)
N2—H23···O19	0.87 (2)	2.09 (2)	2.958 (3)	172 (2)
N2—H24···O4^vii	0.88 (2)	2.27 (2)	3.118 (3)	162 (2)
O19—H191···O1^vi	0.73 (2)	2.17 (2)	2.835 (3)	151 (2)
O19—H192···O14	0.74 (2)	2.23 (2)	2.933 (3)	160 (2)
N3—H31···O2^vi	0.88 (2)	1.98 (2)	2.819 (3)	159 (2)
N3—H32···O5	0.86 (2)	2.03 (2)	2.880 (3)	175 (2)
N3—H33···O17^viii	0.88 (2)	2.11 (2)	2.989 (3)	172 (2)
N3—H34···O6^ix	0.87 (2)	2.14 (2)	2.953 (3)	157 (2)
N3—H34···O7^ix	0.87 (2)	2.27 (2)	2.838 (3)	124 (2)
N4—H41···O10^iv	0.87 (2)	2.28 (2)	3.020 (3)	143 (2)
N4—H42···O19	0.87 (2)	2.15 (2)	2.965 (3)	155 (2)
N4—H42···O11^iii	0.87 (2)	2.38 (2)	2.818 (3)	111 (2)
N4—H43···O3^iv	0.87 (2)	2.27 (2)	2.975 (3)	139 (2)
N4—H43···O2^iv	0.86 (2)	2.29 (2)	2.945 (3)	133 (2)
N4—H44···O7^vii	0.88 (2)	1.90 (2)	2.769 (3)	169 (2)

Symmetry codes: (ii) −x, y−1/2, −z+1/2; (iii) −x, y+1/2, −z+1/2; (iv) x, −y+1/2, z−1/2; (v) x, y+1, z; (vi) −x+1, y+1/2, −z+1/2; (vii) x, −y+3/2, z−1/2; (viii) x+1, y, z; (ix) −x+1, y−1/2, −z+1/2.