Diaqua­tetra­kis­(1H-imidazole)copper(II) bis­[tris­(1H-imidazole)(pyridine-2,4,6-tricarboxyl­ato-κ³N,O²:O⁶)cuprate(II)] dihydrate

The asymmetric unit of the title complex, [Cu(C₃H₄N₂)₄(H₂O)₂][Cu(C₈H₂NO₆)(C₃H₄N₂)₃]₂·2H₂O, contains half of a centrosymmetric diaqua­tetra­kis­(1H-imidazole)copper(II) cat­ion and a complex anion comprising copper(II) coord­inated by a pyridine-2,4,6-tricarboxyl­ate anion and three imidazole ligands, together with a water molecule.

Key indicators

• Single-crystal X-ray study
• T = 143 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.025
• wR factor = 0.070
• Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Cu2    -   N8      ..       5.22 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Cu1    -   O1      ..       6.35 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Cu1    -   N1      ..       5.85 su
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C10    -   C11    ...       1.53 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          3
              H2 O

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

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

---

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1997); software used to prepare material for publication: SHELXTL.

Diaquatetrakis(1H-imidazole)copper(II) bis[tris(1H-imidazole)(pyridine-2,4,6-tricarboxylato- κ³N,O²:O⁶)cuprate(II)] dihydrate

Crystal data

[Cu(C3H4N2)4(H2O)2][Cu(C8H2NO6)(C3H4N2)3]2·2H2O	Z = 1
Mr = 1359.72	F(000) = 697
Triclinic, P1	Dx = 1.619 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.7101 (6) Å	Cell parameters from 5941 reflections
b = 11.8947 (8) Å	θ = 2.8–28.3°
c = 15.1194 (10) Å	µ = 1.22 mm^−1
α = 109.920 (1)°	T = 143 K
β = 102.599 (1)°	Prism, blue
γ = 98.444 (1)°	0.56 × 0.46 × 0.32 mm
V = 1394.87 (16) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	5985 independent reflections
Radiation source: fine-focus sealed tube	5821 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.013
ω scans	θmax = 27.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −10→11
Tmin = 0.531, Tmax = 0.675	k = −15→15
13967 measured reflections	l = −19→19

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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.070	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0379P)^2 + 0.8171P] where P = (Fo^2 + 2Fc^2)/3
5985 reflections	(Δ/σ)max = 0.004
410 parameters	Δρmax = 0.45 e Å^−3
5 restraints	Δρmin = −0.54 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	0.5000	0.5000	0.5000	0.01543 (7)
Cu2	0.51739 (2)	0.826185 (15)	0.184665 (12)	0.01487 (6)
O1	0.25464 (16)	0.57696 (12)	0.45024 (11)	0.0347 (3)
O2	0.59710 (13)	0.96655 (9)	0.36311 (8)	0.0186 (2)
O3	0.72576 (15)	1.16332 (10)	0.45614 (8)	0.0248 (2)
O4	0.98871 (13)	1.41727 (10)	0.30003 (8)	0.0226 (2)
O5	0.98279 (16)	1.32338 (11)	0.14304 (9)	0.0348 (3)
O6	0.75496 (13)	0.86860 (10)	−0.01712 (8)	0.0213 (2)
O7	0.53985 (14)	0.79567 (10)	0.02435 (8)	0.0228 (2)
N1	0.49013 (15)	0.41641 (11)	0.35890 (9)	0.0181 (2)
N2	0.39676 (17)	0.30269 (12)	0.20098 (9)	0.0225 (3)
H2A	0.3302	0.2501	0.1442	0.027*
N3	0.35683 (15)	0.34663 (11)	0.49690 (9)	0.0174 (2)
N4	0.29333 (17)	0.18845 (13)	0.53657 (10)	0.0249 (3)
H4A	0.3043	0.1299	0.5589	0.030*
N5	0.65755 (14)	0.99053 (11)	0.20271 (8)	0.0134 (2)
N6	0.37761 (15)	0.65750 (11)	0.14108 (10)	0.0191 (2)
N7	0.20233 (17)	0.49456 (12)	0.12606 (10)	0.0250 (3)
H7A	0.1351	0.4455	0.1405	0.030*
N8	0.72119 (16)	0.76927 (11)	0.22049 (9)	0.0188 (2)
N9	0.97666 (17)	0.76968 (13)	0.27530 (11)	0.0254 (3)
H9A	1.0827	0.7962	0.2991	0.030*
N10	0.31727 (15)	0.89172 (11)	0.16579 (9)	0.0183 (2)
N11	0.07785 (16)	0.90624 (13)	0.09285 (10)	0.0233 (3)
H11A	−0.0176	0.8873	0.0499	0.028*
C1	0.60809 (19)	0.43574 (15)	0.31446 (11)	0.0231 (3)
H1A	0.7129	0.4895	0.3470	0.028*
C2	0.55040 (19)	0.36533 (14)	0.21642 (11)	0.0218 (3)
H2B	0.6063	0.3609	0.1684	0.026*
C3	0.3652 (2)	0.33548 (15)	0.28781 (11)	0.0243 (3)
H3A	0.2656	0.3045	0.2971	0.029*
C4	0.19010 (19)	0.30826 (15)	0.47134 (12)	0.0247 (3)
H4B	0.1153	0.3445	0.4414	0.030*
C5	0.1501 (2)	0.21029 (16)	0.49594 (13)	0.0287 (4)
H5A	0.0440	0.1660	0.4868	0.034*
C6	0.41392 (19)	0.27226 (14)	0.53630 (11)	0.0215 (3)
H6A	0.5259	0.2775	0.5612	0.026*
C7	0.67275 (17)	1.07290 (13)	0.37669 (10)	0.0154 (3)
C8	0.70777 (16)	1.09070 (12)	0.28735 (10)	0.0139 (3)
C9	0.79741 (17)	1.20195 (12)	0.29493 (10)	0.0153 (3)
H9B	0.8295	1.2718	0.3551	0.018*
C10	0.83973 (17)	1.20999 (13)	0.21316 (10)	0.0151 (3)
C11	0.94588 (17)	1.32837 (13)	0.21947 (11)	0.0180 (3)
C12	0.79171 (17)	1.10484 (13)	0.12708 (10)	0.0159 (3)
H12A	0.8201	1.1071	0.0704	0.019*
C13	0.70183 (17)	0.99636 (13)	0.12442 (10)	0.0149 (3)
C14	0.65919 (17)	0.87571 (13)	0.03563 (10)	0.0165 (3)
C15	0.3464 (2)	0.56921 (15)	0.04813 (12)	0.0272 (3)
H15A	0.3930	0.5775	−0.0012	0.033*
C16	0.2376 (2)	0.46796 (15)	0.03866 (13)	0.0325 (4)
H16A	0.1946	0.3934	−0.0178	0.039*
C17	0.28836 (19)	0.60872 (14)	0.18584 (12)	0.0215 (3)
H17A	0.2859	0.6493	0.2514	0.026*
C18	0.7317 (2)	0.65283 (14)	0.21557 (13)	0.0251 (3)
H18A	0.6422	0.5836	0.1919	0.030*
C19	0.8885 (2)	0.65197 (15)	0.24959 (14)	0.0291 (4)
H19A	0.9293	0.5839	0.2546	0.035*
C20	0.87247 (19)	0.83670 (15)	0.25770 (12)	0.0231 (3)
H20A	0.9029	0.9219	0.2703	0.028*
C21	0.2910 (2)	1.00286 (15)	0.21931 (13)	0.0253 (3)
H21A	0.3647	1.0634	0.2783	0.030*
C22	0.1434 (2)	1.01220 (16)	0.17465 (14)	0.0285 (3)
H22A	0.0950	1.0793	0.1961	0.034*
C23	0.18561 (19)	0.83619 (15)	0.08996 (11)	0.0212 (3)
H23A	0.1696	0.7572	0.0401	0.025*
O8	0.70187 (15)	1.14280 (12)	0.62368 (9)	0.0289 (3)
H1D	0.173 (2)	0.5344 (19)	0.4025 (14)	0.043 (6)*
H1E	0.238 (3)	0.6432 (16)	0.4819 (15)	0.037 (6)*
H8D	0.696 (3)	1.128 (2)	0.5626 (13)	0.061 (8)*
H8E	0.609 (2)	1.103 (2)	0.6229 (19)	0.057 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.01862 (13)	0.01153 (12)	0.01181 (12)	−0.00098 (9)	0.00222 (9)	0.00253 (9)
Cu2	0.01513 (10)	0.01081 (9)	0.01832 (10)	0.00000 (6)	0.00592 (7)	0.00579 (7)
O1	0.0261 (6)	0.0180 (6)	0.0410 (7)	0.0030 (5)	−0.0053 (6)	−0.0012 (5)
O2	0.0224 (5)	0.0163 (5)	0.0190 (5)	0.0015 (4)	0.0083 (4)	0.0089 (4)
O3	0.0364 (6)	0.0190 (5)	0.0155 (5)	−0.0013 (5)	0.0103 (5)	0.0039 (4)
O4	0.0239 (6)	0.0145 (5)	0.0236 (5)	−0.0026 (4)	0.0049 (4)	0.0046 (4)
O5	0.0442 (8)	0.0270 (6)	0.0238 (6)	−0.0167 (6)	0.0120 (5)	0.0075 (5)
O6	0.0206 (5)	0.0231 (5)	0.0144 (5)	−0.0011 (4)	0.0069 (4)	0.0016 (4)
O7	0.0267 (6)	0.0164 (5)	0.0195 (5)	−0.0042 (4)	0.0092 (4)	0.0022 (4)
N1	0.0206 (6)	0.0151 (6)	0.0158 (6)	0.0022 (5)	0.0038 (5)	0.0044 (5)
N2	0.0248 (7)	0.0207 (6)	0.0142 (6)	0.0013 (5)	0.0022 (5)	0.0012 (5)
N3	0.0194 (6)	0.0146 (6)	0.0149 (5)	0.0001 (5)	0.0027 (5)	0.0044 (5)
N4	0.0283 (7)	0.0215 (6)	0.0267 (7)	0.0018 (5)	0.0054 (6)	0.0145 (5)
N5	0.0142 (5)	0.0122 (5)	0.0139 (5)	0.0011 (4)	0.0045 (4)	0.0057 (4)
N6	0.0187 (6)	0.0135 (6)	0.0249 (6)	0.0009 (5)	0.0091 (5)	0.0068 (5)
N7	0.0285 (7)	0.0172 (6)	0.0283 (7)	−0.0034 (5)	0.0126 (6)	0.0084 (5)
N8	0.0207 (6)	0.0155 (6)	0.0218 (6)	0.0033 (5)	0.0082 (5)	0.0083 (5)
N9	0.0203 (7)	0.0266 (7)	0.0305 (7)	0.0063 (5)	0.0067 (5)	0.0127 (6)
N10	0.0176 (6)	0.0168 (6)	0.0207 (6)	0.0015 (5)	0.0065 (5)	0.0079 (5)
N11	0.0175 (6)	0.0292 (7)	0.0246 (7)	0.0023 (5)	0.0043 (5)	0.0143 (6)
C1	0.0213 (7)	0.0231 (7)	0.0196 (7)	0.0003 (6)	0.0062 (6)	0.0038 (6)
C2	0.0259 (8)	0.0199 (7)	0.0191 (7)	0.0050 (6)	0.0088 (6)	0.0058 (6)
C3	0.0230 (8)	0.0243 (8)	0.0176 (7)	−0.0022 (6)	0.0053 (6)	0.0023 (6)
C4	0.0208 (8)	0.0234 (8)	0.0265 (8)	0.0005 (6)	0.0006 (6)	0.0114 (6)
C5	0.0229 (8)	0.0277 (8)	0.0314 (9)	−0.0039 (6)	0.0021 (7)	0.0142 (7)
C6	0.0221 (7)	0.0203 (7)	0.0222 (7)	0.0039 (6)	0.0051 (6)	0.0099 (6)
C7	0.0162 (6)	0.0168 (6)	0.0154 (6)	0.0039 (5)	0.0066 (5)	0.0075 (5)
C8	0.0145 (6)	0.0134 (6)	0.0142 (6)	0.0024 (5)	0.0046 (5)	0.0059 (5)
C9	0.0167 (7)	0.0122 (6)	0.0148 (6)	0.0011 (5)	0.0041 (5)	0.0037 (5)
C10	0.0141 (6)	0.0140 (6)	0.0172 (6)	0.0007 (5)	0.0038 (5)	0.0073 (5)
C11	0.0168 (7)	0.0153 (6)	0.0204 (7)	−0.0012 (5)	0.0034 (5)	0.0084 (6)
C12	0.0166 (7)	0.0157 (6)	0.0146 (6)	0.0000 (5)	0.0049 (5)	0.0063 (5)
C13	0.0153 (6)	0.0144 (6)	0.0143 (6)	0.0018 (5)	0.0046 (5)	0.0051 (5)
C14	0.0189 (7)	0.0152 (6)	0.0131 (6)	0.0007 (5)	0.0029 (5)	0.0050 (5)
C15	0.0350 (9)	0.0186 (7)	0.0252 (8)	−0.0028 (6)	0.0152 (7)	0.0049 (6)
C16	0.0430 (10)	0.0192 (8)	0.0280 (9)	−0.0070 (7)	0.0161 (8)	0.0028 (7)
C17	0.0230 (7)	0.0163 (7)	0.0251 (7)	0.0007 (6)	0.0105 (6)	0.0071 (6)
C18	0.0270 (8)	0.0154 (7)	0.0319 (8)	0.0040 (6)	0.0071 (7)	0.0091 (6)
C19	0.0305 (9)	0.0217 (8)	0.0379 (9)	0.0105 (7)	0.0092 (7)	0.0138 (7)
C20	0.0220 (8)	0.0193 (7)	0.0295 (8)	0.0041 (6)	0.0081 (6)	0.0111 (6)
C21	0.0214 (8)	0.0194 (7)	0.0299 (8)	0.0041 (6)	0.0042 (6)	0.0055 (6)
C22	0.0218 (8)	0.0246 (8)	0.0368 (9)	0.0064 (6)	0.0059 (7)	0.0101 (7)
C23	0.0212 (7)	0.0234 (7)	0.0185 (7)	0.0017 (6)	0.0058 (6)	0.0090 (6)
O8	0.0241 (6)	0.0416 (7)	0.0205 (6)	−0.0005 (5)	0.0062 (5)	0.0148 (5)

Geometric parameters (Å, º)

Cu1—N1	1.9991 (12)	N9—C19	1.373 (2)
Cu1—N1^i	1.9991 (12)	N9—H9A	0.8800
Cu1—N3^i	2.0331 (12)	N10—C23	1.324 (2)
Cu1—N3	2.0331 (12)	N10—C21	1.377 (2)
Cu1—O1	2.5127 (13)	N11—C23	1.342 (2)
Cu2—N6	1.9935 (12)	N11—C22	1.365 (2)
Cu2—N10	2.0152 (13)	N11—H11A	0.8800
Cu2—N8	2.0214 (13)	C1—C2	1.363 (2)
Cu2—N5	2.0437 (12)	C1—H1A	0.9500
Cu2—O7	2.3819 (11)	C2—H2B	0.9500
Cu2—O2	2.5143 (11)	C3—H3A	0.9500
O1—H1D	0.839 (16)	C4—C5	1.360 (2)
O1—H1E	0.824 (15)	C4—H4B	0.9500
O2—C7	1.2633 (17)	C5—H5A	0.9500
O3—C7	1.2429 (18)	C6—H6A	0.9500
O4—C11	1.2447 (18)	C7—C8	1.5225 (18)
O5—C11	1.2503 (19)	C8—C9	1.3885 (19)
O6—C14	1.2666 (18)	C9—C10	1.3937 (19)
O7—C14	1.2399 (18)	C9—H9B	0.9500
N1—C3	1.320 (2)	C10—C12	1.3902 (19)
N1—C1	1.377 (2)	C10—C11	1.5279 (19)
N2—C3	1.338 (2)	C12—C13	1.3906 (19)
N2—C2	1.361 (2)	C12—H12A	0.9500
N2—H2A	0.8800	C13—C14	1.5208 (19)
N3—C6	1.320 (2)	C15—C16	1.363 (2)
N3—C4	1.381 (2)	C15—H15A	0.9500
N4—C6	1.339 (2)	C16—H16A	0.9500
N4—C5	1.368 (2)	C17—H17A	0.9500
N4—H4A	0.8800	C18—C19	1.354 (2)
N5—C13	1.3423 (18)	C18—H18A	0.9500
N5—C8	1.3463 (17)	C19—H19A	0.9500
N6—C17	1.3280 (19)	C20—H20A	0.9500
N6—C15	1.377 (2)	C21—C22	1.355 (2)
N7—C17	1.339 (2)	C21—H21A	0.9500
N7—C16	1.364 (2)	C22—H22A	0.9500
N7—H7A	0.8800	C23—H23A	0.9500
N8—C20	1.325 (2)	O8—H8D	0.868 (16)
N8—C18	1.3791 (19)	O8—H8E	0.870 (16)
N9—C20	1.335 (2)
N1—Cu1—N1^i	180.0	N2—C2—H2B	126.8
N1—Cu1—N3^i	88.49 (5)	C1—C2—H2B	126.8
N1^i—Cu1—N3^i	91.51 (5)	N1—C3—N2	111.36 (14)
N1—Cu1—N3	91.51 (5)	N1—C3—H3A	124.3
N1^i—Cu1—N3	88.49 (5)	N2—C3—H3A	124.3
N3^i—Cu1—N3	180.0	C5—C4—N3	109.13 (14)
N1—Cu1—O1	90.23 (5)	C5—C4—H4B	125.4
N1^i—Cu1—O1	89.77 (5)	N3—C4—H4B	125.4
N3^i—Cu1—O1	89.39 (5)	C4—C5—N4	106.18 (14)
N3—Cu1—O1	90.61 (5)	C4—C5—H5A	126.9
N6—Cu2—N10	89.63 (5)	N4—C5—H5A	126.9
N6—Cu2—N8	92.00 (5)	N3—C6—N4	111.14 (14)
N10—Cu2—N8	173.35 (5)	N3—C6—H6A	124.4
N6—Cu2—N5	169.50 (5)	N4—C6—H6A	124.4
N10—Cu2—N5	90.33 (5)	O3—C7—O2	126.56 (13)
N8—Cu2—N5	89.23 (5)	O3—C7—C8	116.77 (12)
N6—Cu2—O7	93.31 (5)	O2—C7—C8	116.63 (12)
N10—Cu2—O7	94.16 (5)	N5—C8—C9	122.01 (12)
N8—Cu2—O7	92.18 (5)	N5—C8—C7	116.36 (11)
N5—Cu2—O7	76.23 (4)	C9—C8—C7	121.46 (12)
N6—Cu2—O2	119.06 (4)	C8—C9—C10	119.23 (13)
N10—Cu2—O2	87.92 (4)	C8—C9—H9B	120.4
N8—Cu2—O2	85.66 (4)	C10—C9—H9B	120.4
N5—Cu2—O2	71.42 (4)	C12—C10—C9	118.22 (12)
O7—Cu2—O2	147.60 (3)	C12—C10—C11	120.54 (12)
Cu1—O1—H1D	124.0 (16)	C9—C10—C11	121.10 (12)
Cu1—O1—H1E	125.2 (16)	O4—C11—O5	127.51 (13)
H1D—O1—H1E	110 (2)	O4—C11—C10	116.79 (13)
C7—O2—Cu2	110.93 (8)	O5—C11—C10	115.68 (13)
C14—O7—Cu2	106.16 (9)	C13—C12—C10	119.62 (13)
C3—N1—C1	105.62 (13)	C13—C12—H12A	120.2
C3—N1—Cu1	126.84 (11)	C10—C12—H12A	120.2
C1—N1—Cu1	127.45 (10)	N5—C13—C12	121.70 (13)
C3—N2—C2	107.60 (13)	N5—C13—C14	116.20 (12)
C3—N2—H2A	126.2	C12—C13—C14	121.94 (12)
C2—N2—H2A	126.2	O7—C14—O6	127.70 (13)
C6—N3—C4	105.82 (13)	O7—C14—C13	117.59 (13)
C6—N3—Cu1	122.95 (11)	O6—C14—C13	114.68 (12)
C4—N3—Cu1	130.45 (10)	C16—C15—N6	108.73 (14)
C6—N4—C5	107.73 (13)	C16—C15—H15A	125.6
C6—N4—H4A	126.1	N6—C15—H15A	125.6
C5—N4—H4A	126.1	C15—C16—N7	106.62 (14)
C13—N5—C8	119.13 (12)	C15—C16—H16A	126.7
C13—N5—Cu2	116.74 (9)	N7—C16—H16A	126.7
C8—N5—Cu2	124.12 (9)	N6—C17—N7	110.81 (14)
C17—N6—C15	106.11 (12)	N6—C17—H17A	124.6
C17—N6—Cu2	130.87 (11)	N7—C17—H17A	124.6
C15—N6—Cu2	122.82 (10)	C19—C18—N8	109.82 (14)
C17—N7—C16	107.74 (13)	C19—C18—H18A	125.1
C17—N7—H7A	126.1	N8—C18—H18A	125.1
C16—N7—H7A	126.1	C18—C19—N9	105.89 (14)
C20—N8—C18	105.21 (13)	C18—C19—H19A	127.1
C20—N8—Cu2	127.52 (11)	N9—C19—H19A	127.1
C18—N8—Cu2	127.21 (11)	N8—C20—N9	111.42 (14)
C20—N9—C19	107.66 (14)	N8—C20—H20A	124.3
C20—N9—H9A	126.2	N9—C20—H20A	124.3
C19—N9—H9A	126.2	C22—C21—N10	109.25 (15)
C23—N10—C21	105.72 (13)	C22—C21—H21A	125.4
C23—N10—Cu2	124.37 (11)	N10—C21—H21A	125.4
C21—N10—Cu2	129.65 (11)	C21—C22—N11	106.54 (15)
C23—N11—C22	107.49 (13)	C21—C22—H22A	126.7
C23—N11—H11A	126.3	N11—C22—H22A	126.7
C22—N11—H11A	126.3	N10—C23—N11	111.00 (14)
C2—C1—N1	109.08 (14)	N10—C23—H23A	124.5
C2—C1—H1A	125.5	N11—C23—H23A	124.5
N1—C1—H1A	125.5	H8D—O8—H8E	105 (2)
N2—C2—C1	106.33 (13)
N6—Cu2—O2—C7	−174.04 (9)	Cu1—N1—C3—N2	176.67 (10)
N10—Cu2—O2—C7	−85.61 (10)	C2—N2—C3—N1	0.16 (19)
N8—Cu2—O2—C7	96.09 (10)	C6—N3—C4—C5	−0.18 (18)
N5—Cu2—O2—C7	5.44 (9)	Cu1—N3—C4—C5	−170.10 (12)
O7—Cu2—O2—C7	8.88 (13)	N3—C4—C5—N4	−0.2 (2)
N6—Cu2—O7—C14	−161.45 (10)	C6—N4—C5—C4	0.4 (2)
N10—Cu2—O7—C14	108.67 (10)	C4—N3—C6—N4	0.47 (18)
N8—Cu2—O7—C14	−69.32 (10)	Cu1—N3—C6—N4	171.34 (10)
N5—Cu2—O7—C14	19.35 (10)	C5—N4—C6—N3	−0.58 (19)
O2—Cu2—O7—C14	16.00 (14)	Cu2—O2—C7—O3	178.71 (13)
N3^i—Cu1—N1—C3	−144.63 (14)	Cu2—O2—C7—C8	−3.67 (15)
N3—Cu1—N1—C3	35.37 (14)	C13—N5—C8—C9	3.3 (2)
O1—Cu1—N1—C3	−55.24 (14)	Cu2—N5—C8—C9	−177.31 (10)
N3^i—Cu1—N1—C1	31.58 (13)	C13—N5—C8—C7	−171.99 (12)
N3—Cu1—N1—C1	−148.42 (13)	Cu2—N5—C8—C7	7.43 (17)
O1—Cu1—N1—C1	120.96 (13)	O3—C7—C8—N5	176.54 (13)
N1—Cu1—N3—C6	103.94 (12)	O2—C7—C8—N5	−1.32 (19)
N1^i—Cu1—N3—C6	−76.06 (12)	O3—C7—C8—C9	1.3 (2)
O1—Cu1—N3—C6	−165.82 (12)	O2—C7—C8—C9	−176.60 (13)
N1—Cu1—N3—C4	−87.63 (14)	N5—C8—C9—C10	−1.3 (2)
N1^i—Cu1—N3—C4	92.37 (14)	C7—C8—C9—C10	173.73 (13)
O1—Cu1—N3—C4	2.61 (14)	C8—C9—C10—C12	−0.8 (2)
N6—Cu2—N5—C13	−9.9 (3)	C8—C9—C10—C11	−176.69 (13)
N10—Cu2—N5—C13	−99.65 (10)	C12—C10—C11—O4	−177.48 (13)
N8—Cu2—N5—C13	86.99 (11)	C9—C10—C11—O4	−1.7 (2)
O7—Cu2—N5—C13	−5.44 (10)	C12—C10—C11—O5	0.9 (2)
O2—Cu2—N5—C13	172.66 (11)	C9—C10—C11—O5	176.65 (14)
N6—Cu2—N5—C8	170.7 (2)	C9—C10—C12—C13	1.0 (2)
N10—Cu2—N5—C8	80.92 (11)	C11—C10—C12—C13	176.83 (13)
N8—Cu2—N5—C8	−92.45 (11)	C8—N5—C13—C12	−3.1 (2)
O7—Cu2—N5—C8	175.12 (12)	Cu2—N5—C13—C12	177.41 (11)
O2—Cu2—N5—C8	−6.78 (10)	C8—N5—C13—C14	172.44 (12)
N10—Cu2—N6—C17	−72.41 (15)	Cu2—N5—C13—C14	−7.03 (16)
N8—Cu2—N6—C17	101.14 (15)	C10—C12—C13—N5	1.0 (2)
N5—Cu2—N6—C17	−162.3 (2)	C10—C12—C13—C14	−174.27 (13)
O7—Cu2—N6—C17	−166.56 (14)	Cu2—O7—C14—O6	149.09 (13)
O2—Cu2—N6—C17	15.00 (16)	Cu2—O7—C14—C13	−28.87 (14)
N10—Cu2—N6—C15	101.66 (13)	N5—C13—C14—O7	27.42 (19)
N8—Cu2—N6—C15	−84.78 (13)	C12—C13—C14—O7	−157.03 (14)
N5—Cu2—N6—C15	11.8 (4)	N5—C13—C14—O6	−150.81 (13)
O7—Cu2—N6—C15	7.51 (13)	C12—C13—C14—O6	24.7 (2)
O2—Cu2—N6—C15	−170.93 (12)	C17—N6—C15—C16	0.1 (2)
N6—Cu2—N8—C20	−179.54 (14)	Cu2—N6—C15—C16	−175.24 (13)
N5—Cu2—N8—C20	10.89 (14)	N6—C15—C16—N7	0.0 (2)
O7—Cu2—N8—C20	87.07 (13)	C17—N7—C16—C15	−0.1 (2)
O2—Cu2—N8—C20	−60.54 (13)	C15—N6—C17—N7	−0.14 (19)
N6—Cu2—N8—C18	−2.77 (13)	Cu2—N6—C17—N7	174.68 (11)
N5—Cu2—N8—C18	−172.35 (13)	C16—N7—C17—N6	0.1 (2)
O7—Cu2—N8—C18	−96.16 (13)	C20—N8—C18—C19	−0.12 (19)
O2—Cu2—N8—C18	116.22 (13)	Cu2—N8—C18—C19	−177.47 (12)
N6—Cu2—N10—C23	−42.36 (12)	N8—C18—C19—N9	−0.4 (2)
N5—Cu2—N10—C23	127.15 (12)	C20—N9—C19—C18	0.84 (19)
O7—Cu2—N10—C23	50.93 (12)	C18—N8—C20—N9	0.67 (18)
O2—Cu2—N10—C23	−161.46 (12)	Cu2—N8—C20—N9	178.00 (10)
N6—Cu2—N10—C21	144.34 (14)	C19—N9—C20—N8	−0.96 (19)
N5—Cu2—N10—C21	−46.16 (14)	C23—N10—C21—C22	0.06 (18)
O7—Cu2—N10—C21	−122.38 (14)	Cu2—N10—C21—C22	174.32 (11)
O2—Cu2—N10—C21	25.24 (14)	N10—C21—C22—N11	−0.1 (2)
C3—N1—C1—C2	0.17 (18)	C23—N11—C22—C21	0.05 (19)
Cu1—N1—C1—C2	−176.68 (11)	C21—N10—C23—N11	−0.03 (17)
C3—N2—C2—C1	−0.04 (18)	Cu2—N10—C23—N11	−174.68 (9)
N1—C1—C2—N2	−0.08 (18)	C22—N11—C23—N10	−0.01 (18)
C1—N1—C3—N2	−0.20 (19)

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
N2—H2A···O6^ii	0.88	1.86	2.7152 (16)	164
N4—H4A···O2^i	0.88	2.05	2.8986 (17)	161
N7—H7A···O5^iii	0.88	1.83	2.7009 (17)	168
N9—H9A···O8^iv	0.88	1.86	2.7297 (19)	167
N11—H11A···O6^v	0.88	1.96	2.8209 (17)	166
O1—H1D···O4^iii	0.84 (2)	1.93 (2)	2.7576 (17)	171 (2)
O1—H1E···O3^vi	0.82 (2)	2.11 (2)	2.8873 (17)	157 (2)
O8—H8D···O3	0.87 (2)	1.85 (2)	2.6750 (16)	157 (3)
O8—H8E···O2^vi	0.87 (2)	1.95 (2)	2.8146 (16)	172 (3)

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