Crystal structure of poly[[(μ₃-hydroxido-κ³O:O:O)(μ₃-selenato-κ³O¹:O²:O³)tris­[μ₃-2-(1,2,4-triazol-4-yl)acetato-κ³N¹:N²:O]tricopper(II)] dihydrate]

The self-assembly of Cu^II selenate and 1,2,4-triazol-4-yl-acetic acid (trgly-H) in aqueous solution under hydro­thermal conditions affords a two-dimensional coordination network ([Cu₃(μ₃-OH)(trgly)₃(SeO₄)]·2H₂O) based on triangular coordination clusters [Cu₃(μ₃-OH)] as secondary building units (SBUs). The trinuclear motif is supported by three [N—N] triazole bridges and a facially coordinating tripodal SeO₄²⁻ anion. This results in a less distorted square-pyramidal arrangement around the five-coordinate copper(II) centres in comparison to that of the analogous isomorphous Cu₃(μ₃-OH)(trgly)₃(SO₄)]·2H₂O complex.

Key indicators

• Single-crystal X-ray study
• T = 213 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.032
• wR factor = 0.072
• Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT220_ALERT_2_C Non-Solvent  Resd 1  O   Ueq(max)/Ueq(min) Range        3.3 Ratio
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1 Note
              C12 H13 Cu3 N9 O11 Se
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          5 Report

Alert level G
PLAT004_ALERT_5_G Polymeric Structure Found with Maximum Dimension          2 Info
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          5 Report
PLAT794_ALERT_5_G Tentative Bond Valency for Cu1       (II)      .       2.21 Info
PLAT794_ALERT_5_G Tentative Bond Valency for Cu2       (II)      .       2.20 Info
PLAT794_ALERT_5_G Tentative Bond Valency for Cu3       (II)      .       2.15 Info
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          1 Info
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         10 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          2 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   8 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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
   3 ALERT type 4 Improvement, methodology, query or suggestion
   5 ALERT type 5 Informative message, check

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Computing details

Data collection: IPDS Software (Stoe & Cie, 2000); cell refinement: IPDS Software (Stoe & Cie, 2000); data reduction: IPDS Software (Stoe & Cie, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: WinGX (Farrugia, 2012).

Poly[[(µ₃-hydroxido-κ³O:O:O)(µ₃-selenato-κ³O¹:O²:O³)tris[µ₃-2-(1,2,4-triazol-4-yl)acetato-κ³N¹:N²:O]tricopper(II)] dihydrate]

Crystal data

[Cu3(C4H4N3O9)3(SeO4)(OH)]·2H2O	F(000) = 1508
Mr = 764.92	Dx = 2.308 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.9403 (8) Å	Cell parameters from 8000 reflections
b = 17.5393 (15) Å	θ = 2.0–26.8°
c = 12.1289 (9) Å	µ = 4.62 mm^−1
β = 108.965 (8)°	T = 213 K
V = 2201.0 (3) Å^3	Prism, blue
Z = 4	0.20 × 0.16 × 0.14 mm

Data collection

Stoe Image plate diffraction system diffractometer	3306 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.057
φ oscillation scans	θmax = 26.8°, θmin = 2.0°
Absorption correction: numerical [X-RED (Stoe & Cie, 2001) and X-SHAPE (Stoe & Cie, 1999)]	h = −13→13
Tmin = 0.405, Tmax = 0.569	k = −22→22
16928 measured reflections	l = −15→15
4681 independent 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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.072	H-atom parameters constrained
S = 0.88	w = 1/[σ^2(Fo^2) + (0.0392P)^2] where P = (Fo^2 + 2Fc^2)/3
4681 reflections	(Δ/σ)max < 0.001
343 parameters	Δρmax = 0.99 e Å^−3
0 restraints	Δρmin = −0.64 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq
Cu1	0.27623 (5)	0.00328 (2)	0.16661 (4)	0.01311 (11)
Cu2	0.17026 (5)	−0.07181 (2)	0.37617 (4)	0.01200 (11)
Cu3	0.39077 (5)	0.07288 (3)	0.44294 (4)	0.01223 (11)
Se1	0.08793 (4)	0.10530 (2)	0.27442 (3)	0.01415 (10)
O1	0.3177 (3)	−0.01857 (14)	0.3386 (2)	0.0113 (5)
H1O	0.378780	−0.050942	0.354877	0.017*
O2	0.1203 (3)	0.08350 (16)	0.1556 (2)	0.0237 (7)
O3	0.0502 (3)	0.02779 (15)	0.3325 (3)	0.0228 (7)
O4	0.2182 (3)	0.14261 (15)	0.3694 (3)	0.0218 (7)
O5	−0.0323 (3)	0.16534 (15)	0.2454 (3)	0.0231 (7)
O6	0.0419 (3)	−0.36472 (15)	−0.0871 (2)	0.0174 (6)
O7	0.2019 (3)	−0.28370 (17)	−0.0029 (3)	0.0301 (8)
O8	0.2547 (3)	0.02330 (16)	1.0045 (2)	0.0253 (7)
O9	0.3408 (4)	−0.0683 (2)	0.9233 (3)	0.0375 (9)
O10	0.5155 (3)	0.36051 (14)	0.0589 (2)	0.0160 (6)
O11	0.3676 (3)	0.28549 (17)	0.0946 (3)	0.0307 (8)
N1	0.1686 (4)	−0.09003 (18)	0.1341 (3)	0.0148 (7)
N2	0.1237 (4)	−0.11875 (18)	0.2195 (3)	0.0165 (7)
N3	0.0471 (3)	−0.18786 (17)	0.0647 (3)	0.0139 (7)
N4	0.2432 (3)	−0.03365 (18)	0.5386 (3)	0.0142 (7)
N5	0.3327 (3)	0.02449 (18)	0.5642 (3)	0.0152 (7)
N6	0.2564 (4)	0.01245 (19)	0.7085 (3)	0.0177 (8)
N7	0.4666 (3)	0.10867 (18)	0.3243 (3)	0.0135 (7)
N8	0.4102 (4)	0.08493 (17)	0.2103 (3)	0.0143 (7)
N9	0.5346 (3)	0.18128 (17)	0.2111 (3)	0.0146 (7)
C1	0.1208 (4)	−0.1327 (2)	0.0416 (4)	0.0174 (9)
H1	0.135662	−0.125898	−0.029885	0.021*
C2	0.0507 (4)	−0.1772 (2)	0.1748 (4)	0.0180 (9)
H2	0.007193	−0.207386	0.214252	0.022*
C3	−0.0143 (4)	−0.2514 (2)	−0.0127 (3)	0.0151 (8)
H3A	−0.070577	−0.231321	−0.087360	0.018*
H3B	−0.067585	−0.281162	0.022723	0.018*
C4	0.0885 (4)	−0.3024 (2)	−0.0333 (3)	0.0153 (8)
C5	0.1996 (4)	−0.0399 (2)	0.6262 (3)	0.0173 (9)
H5	0.137619	−0.075582	0.631377	0.021*
C6	0.3394 (5)	0.0504 (2)	0.6674 (4)	0.0209 (9)
H6	0.394363	0.089864	0.707040	0.025*
C7	0.2191 (5)	0.0356 (2)	0.8093 (3)	0.0196 (9)
H7A	0.124993	0.030830	0.788261	0.024*
H7B	0.240617	0.089592	0.824842	0.024*
C8	0.2803 (4)	−0.0084 (2)	0.9205 (4)	0.0202 (9)
C9	0.5423 (4)	0.1668 (2)	0.3220 (4)	0.0156 (8)
H9	0.593603	0.193848	0.387670	0.019*
C10	0.4526 (4)	0.1297 (2)	0.1453 (4)	0.0174 (9)
H10	0.429103	0.126325	0.063676	0.021*
C11	0.5883 (4)	0.2477 (2)	0.1676 (4)	0.0182 (9)
H11A	0.635122	0.230577	0.115612	0.022*
H11B	0.649085	0.275010	0.233175	0.022*
C12	0.4785 (4)	0.3008 (2)	0.1017 (3)	0.0159 (9)
O1W	0.3015 (4)	0.28114 (19)	0.3110 (4)	0.0441 (10)
H1W	0.309086	0.277778	0.243576	0.066*
H2W	0.264986	0.240868	0.323686	0.066*
O2W	0.5427 (4)	0.3544 (2)	0.3669 (3)	0.0408 (9)
H3W	0.576259	0.378437	0.430505	0.061*
H4W	0.471669	0.335127	0.367685	0.061*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0193 (3)	0.0112 (2)	0.0091 (2)	−0.00358 (19)	0.0050 (2)	−0.00138 (17)
Cu2	0.0176 (3)	0.0096 (2)	0.0093 (2)	−0.00239 (19)	0.0050 (2)	−0.00079 (17)
Cu3	0.0169 (3)	0.0109 (2)	0.0091 (2)	−0.00224 (19)	0.0045 (2)	−0.00038 (17)
Se1	0.0155 (2)	0.01058 (17)	0.01497 (19)	0.00218 (16)	0.00297 (17)	0.00008 (15)
O1	0.0139 (16)	0.0091 (12)	0.0104 (12)	−0.0007 (10)	0.0033 (12)	−0.0019 (10)
O2	0.0289 (19)	0.0285 (16)	0.0131 (14)	0.0102 (13)	0.0061 (14)	0.0027 (12)
O3	0.0225 (18)	0.0143 (13)	0.0333 (17)	0.0021 (12)	0.0114 (15)	0.0066 (12)
O4	0.0208 (18)	0.0158 (14)	0.0243 (15)	−0.0005 (12)	0.0013 (14)	−0.0001 (12)
O5	0.0201 (18)	0.0172 (14)	0.0275 (16)	0.0101 (12)	0.0014 (15)	0.0007 (12)
O6	0.0208 (17)	0.0165 (13)	0.0147 (14)	0.0032 (12)	0.0056 (13)	−0.0039 (11)
O7	0.021 (2)	0.0212 (15)	0.046 (2)	0.0001 (14)	0.0079 (17)	−0.0058 (15)
O8	0.045 (2)	0.0250 (15)	0.0092 (13)	−0.0068 (14)	0.0130 (15)	−0.0017 (12)
O9	0.046 (2)	0.045 (2)	0.0257 (17)	0.0226 (18)	0.0176 (18)	0.0120 (16)
O10	0.0215 (17)	0.0116 (13)	0.0151 (14)	0.0002 (11)	0.0063 (13)	0.0023 (10)
O11	0.023 (2)	0.0256 (17)	0.041 (2)	−0.0006 (14)	0.0068 (17)	0.0117 (15)
N1	0.020 (2)	0.0161 (16)	0.0088 (15)	−0.0036 (13)	0.0059 (15)	−0.0001 (12)
N2	0.026 (2)	0.0129 (16)	0.0124 (16)	−0.0029 (14)	0.0086 (16)	−0.0006 (12)
N3	0.018 (2)	0.0099 (15)	0.0123 (16)	−0.0009 (13)	0.0032 (15)	−0.0016 (12)
N4	0.014 (2)	0.0145 (15)	0.0123 (16)	−0.0019 (13)	0.0023 (15)	−0.0024 (13)
N5	0.020 (2)	0.0157 (16)	0.0104 (16)	−0.0047 (14)	0.0050 (15)	−0.0008 (12)
N6	0.023 (2)	0.0201 (17)	0.0100 (16)	−0.0050 (14)	0.0057 (16)	−0.0009 (13)
N7	0.0153 (19)	0.0140 (15)	0.0102 (15)	−0.0015 (14)	0.0028 (15)	0.0001 (12)
N8	0.0177 (19)	0.0147 (16)	0.0096 (15)	−0.0005 (13)	0.0034 (15)	0.0002 (12)
N9	0.019 (2)	0.0107 (15)	0.0165 (17)	−0.0012 (13)	0.0089 (16)	0.0008 (12)
C1	0.023 (3)	0.0138 (18)	0.0154 (19)	−0.0007 (16)	0.0069 (19)	0.0008 (15)
C2	0.026 (3)	0.0131 (18)	0.017 (2)	−0.0056 (16)	0.010 (2)	−0.0036 (15)
C3	0.017 (2)	0.0120 (17)	0.0123 (19)	−0.0029 (15)	0.0001 (18)	−0.0027 (14)
C4	0.021 (3)	0.0128 (18)	0.0108 (18)	−0.0008 (16)	0.0037 (18)	0.0023 (14)
C5	0.020 (3)	0.021 (2)	0.0123 (19)	−0.0051 (17)	0.0077 (19)	−0.0011 (15)
C6	0.027 (3)	0.022 (2)	0.0140 (19)	−0.0078 (18)	0.007 (2)	0.0000 (16)
C7	0.025 (3)	0.022 (2)	0.0127 (19)	−0.0013 (18)	0.0076 (19)	−0.0029 (16)
C8	0.019 (2)	0.023 (2)	0.018 (2)	−0.0069 (18)	0.004 (2)	−0.0012 (17)
C9	0.018 (2)	0.0141 (18)	0.0146 (19)	0.0023 (16)	0.0048 (18)	−0.0006 (15)
C10	0.023 (3)	0.0156 (18)	0.016 (2)	−0.0018 (16)	0.009 (2)	0.0009 (15)
C11	0.021 (3)	0.0146 (19)	0.021 (2)	−0.0025 (17)	0.010 (2)	0.0057 (16)
C12	0.023 (3)	0.0129 (17)	0.0122 (19)	−0.0027 (16)	0.0061 (19)	0.0006 (14)
O1W	0.053 (3)	0.0231 (17)	0.064 (3)	−0.0041 (17)	0.029 (2)	0.0046 (17)
O2W	0.037 (2)	0.054 (2)	0.0280 (19)	−0.0025 (18)	0.0055 (18)	−0.0045 (17)

Geometric parameters (Å, º)

Cu1—O8^i	1.935 (3)	N4—C5	1.303 (5)
Cu1—N1	1.980 (3)	N4—N5	1.377 (4)
Cu1—N8	1.993 (3)	N5—C6	1.311 (5)
Cu1—O1	2.022 (2)	N6—C6	1.346 (5)
Cu1—O2	2.182 (3)	N6—C5	1.349 (5)
Cu2—O6^ii	1.954 (3)	N6—C7	1.466 (5)
Cu2—N2	1.979 (3)	N7—C9	1.320 (5)
Cu2—N4	1.986 (3)	N7—N8	1.382 (4)
Cu2—O1	2.039 (3)	N8—C10	1.301 (5)
Cu2—O3	2.146 (3)	N9—C10	1.339 (5)
Cu3—N5	1.974 (3)	N9—C9	1.345 (5)
Cu3—N7	1.982 (3)	N9—C11	1.478 (5)
Cu3—O10^iii	1.990 (3)	C1—H1	0.9400
Cu3—O1	2.039 (2)	C2—H2	0.9400
Cu3—O4	2.182 (3)	C3—C4	1.520 (6)
Se1—O5	1.632 (3)	C3—H3A	0.9800
Se1—O2	1.637 (3)	C3—H3B	0.9800
Se1—O3	1.645 (3)	C5—H5	0.9400
Se1—O4	1.649 (3)	C6—H6	0.9400
O1—H1O	0.8500	C7—C8	1.509 (6)
O6—C4	1.289 (5)	C7—H7A	0.9800
O7—C4	1.219 (5)	C7—H7B	0.9800
O8—C8	1.270 (5)	C9—H9	0.9400
O9—C8	1.235 (5)	C10—H10	0.9400
O10—C12	1.291 (4)	C11—C12	1.525 (6)
O11—C12	1.218 (5)	C11—H11A	0.9800
N1—C1	1.308 (5)	C11—H11B	0.9800
N1—N2	1.379 (4)	O1W—H1W	0.8500
N2—C2	1.304 (5)	O1W—H2W	0.8500
N3—C2	1.337 (5)	O2W—H3W	0.8500
N3—C1	1.346 (5)	O2W—H4W	0.8500
N3—C3	1.471 (5)
O8^i—Cu1—N1	94.55 (13)	C6—N5—Cu3	129.1 (3)
O8^i—Cu1—N8	88.65 (13)	N4—N5—Cu3	121.9 (2)
N1—Cu1—N8	170.10 (14)	C6—N6—C5	105.5 (3)
O8^i—Cu1—O1	174.35 (13)	C6—N6—C7	125.2 (3)
N1—Cu1—O1	88.18 (11)	C5—N6—C7	128.2 (3)
N8—Cu1—O1	87.86 (12)	C9—N7—N8	107.0 (3)
O8^i—Cu1—O2	89.20 (12)	C9—N7—Cu3	132.3 (3)
N1—Cu1—O2	96.79 (13)	N8—N7—Cu3	118.3 (2)
N8—Cu1—O2	92.62 (13)	C10—N8—N7	107.0 (3)
O1—Cu1—O2	95.40 (10)	C10—N8—Cu1	130.4 (3)
O6^ii—Cu2—N2	90.12 (12)	N7—N8—Cu1	122.2 (2)
O6^ii—Cu2—N4	93.00 (12)	C10—N9—C9	106.3 (3)
N2—Cu2—N4	170.93 (15)	C10—N9—C11	125.9 (3)
O6^ii—Cu2—O1	172.41 (11)	C9—N9—C11	127.1 (3)
N2—Cu2—O1	87.23 (12)	N1—C1—N3	109.4 (3)
N4—Cu2—O1	88.59 (12)	N1—C1—H1	125.3
O6^ii—Cu2—O3	95.29 (11)	N3—C1—H1	125.3
N2—Cu2—O3	98.97 (13)	N2—C2—N3	109.9 (3)
N4—Cu2—O3	89.24 (13)	N2—C2—H2	125.0
O1—Cu2—O3	92.15 (11)	N3—C2—H2	125.0
N5—Cu3—N7	171.64 (14)	N3—C3—C4	110.0 (3)
N5—Cu3—O10^iii	92.21 (12)	N3—C3—H3A	109.7
N7—Cu3—O10^iii	88.56 (12)	C4—C3—H3A	109.7
N5—Cu3—O1	88.15 (12)	N3—C3—H3B	109.7
N7—Cu3—O1	88.32 (12)	C4—C3—H3B	109.7
O10^iii—Cu3—O1	160.30 (11)	H3A—C3—H3B	108.2
N5—Cu3—O4	95.76 (13)	O7—C4—O6	125.3 (4)
N7—Cu3—O4	92.07 (13)	O7—C4—C3	121.7 (3)
O10^iii—Cu3—O4	105.28 (11)	O6—C4—C3	112.9 (4)
O1—Cu3—O4	94.27 (11)	N4—C5—N6	110.1 (4)
O5—Se1—O2	110.53 (15)	N4—C5—H5	125.0
O5—Se1—O3	109.17 (15)	N6—C5—H5	125.0
O2—Se1—O3	109.91 (15)	N5—C6—N6	110.3 (4)
O5—Se1—O4	110.35 (15)	N5—C6—H6	124.9
O2—Se1—O4	108.82 (16)	N6—C6—H6	124.9
O3—Se1—O4	108.01 (15)	N6—C7—C8	116.2 (4)
Cu1—O1—Cu3	113.72 (11)	N6—C7—H7A	108.2
Cu1—O1—Cu2	112.88 (13)	C8—C7—H7A	108.2
Cu3—O1—Cu2	113.63 (11)	N6—C7—H7B	108.2
Cu1—O1—H1O	105.2	C8—C7—H7B	108.2
Cu3—O1—H1O	105.1	H7A—C7—H7B	107.4
Cu2—O1—H1O	105.2	O9—C8—O8	127.3 (4)
Se1—O2—Cu1	119.02 (15)	O9—C8—C7	122.5 (4)
Se1—O3—Cu2	124.02 (16)	O8—C8—C7	110.1 (4)
Se1—O4—Cu3	119.98 (15)	N7—C9—N9	109.3 (4)
C4—O6—Cu2^iv	113.7 (3)	N7—C9—H9	125.3
C8—O8—Cu1^v	138.6 (3)	N9—C9—H9	125.3
C12—O10—Cu3^vi	121.8 (3)	N8—C10—N9	110.4 (4)
C1—N1—N2	107.1 (3)	N8—C10—H10	124.8
C1—N1—Cu1	133.6 (3)	N9—C10—H10	124.8
N2—N1—Cu1	119.1 (2)	N9—C11—C12	109.4 (3)
C2—N2—N1	107.1 (3)	N9—C11—H11A	109.8
C2—N2—Cu2	131.1 (3)	C12—C11—H11A	109.8
N1—N2—Cu2	121.7 (2)	N9—C11—H11B	109.8
C2—N3—C1	106.4 (3)	C12—C11—H11B	109.8
C2—N3—C3	127.1 (3)	H11A—C11—H11B	108.2
C1—N3—C3	126.3 (3)	O11—C12—O10	125.9 (4)
C5—N4—N5	107.5 (3)	O11—C12—C11	120.0 (3)
C5—N4—Cu2	130.2 (3)	O10—C12—C11	114.1 (4)
N5—N4—Cu2	120.0 (2)	H1W—O1W—H2W	108.4
C6—N5—N4	106.7 (3)	H3W—O2W—H4W	108.4
O5—Se1—O2—Cu1	−179.53 (17)	Cu2^iv—O6—C4—C3	176.2 (2)
O3—Se1—O2—Cu1	−59.0 (2)	N3—C3—C4—O7	−10.4 (5)
O4—Se1—O2—Cu1	59.1 (2)	N3—C3—C4—O6	170.9 (3)
O5—Se1—O3—Cu2	175.78 (18)	N5—N4—C5—N6	0.4 (5)
O2—Se1—O3—Cu2	54.4 (2)	Cu2—N4—C5—N6	−161.7 (3)
O4—Se1—O3—Cu2	−64.2 (2)	C6—N6—C5—N4	−1.1 (5)
O5—Se1—O4—Cu3	172.90 (16)	C7—N6—C5—N4	167.1 (4)
O2—Se1—O4—Cu3	−65.7 (2)	N4—N5—C6—N6	−1.2 (5)
O3—Se1—O4—Cu3	53.6 (2)	Cu3—N5—C6—N6	161.3 (3)
C1—N1—N2—C2	−0.1 (5)	C5—N6—C6—N5	1.4 (5)
Cu1—N1—N2—C2	176.8 (3)	C7—N6—C6—N5	−167.2 (4)
C1—N1—N2—Cu2	−179.7 (3)	C6—N6—C7—C8	−103.6 (5)
Cu1—N1—N2—Cu2	−2.8 (4)	C5—N6—C7—C8	90.4 (5)
C5—N4—N5—C6	0.4 (5)	Cu1^v—O8—C8—O9	−4.3 (8)
Cu2—N4—N5—C6	164.7 (3)	Cu1^v—O8—C8—C7	172.5 (3)
C5—N4—N5—Cu3	−163.6 (3)	N6—C7—C8—O9	−11.9 (6)
Cu2—N4—N5—Cu3	0.7 (4)	N6—C7—C8—O8	171.1 (4)
C9—N7—N8—C10	−0.7 (4)	N8—N7—C9—N9	0.8 (4)
Cu3—N7—N8—C10	163.8 (3)	Cu3—N7—C9—N9	−160.7 (3)
C9—N7—N8—Cu1	−175.1 (3)	C10—N9—C9—N7	−0.6 (5)
Cu3—N7—N8—Cu1	−10.5 (4)	C11—N9—C9—N7	170.5 (4)
N2—N1—C1—N3	−0.1 (5)	N7—N8—C10—N9	0.4 (5)
Cu1—N1—C1—N3	−176.4 (3)	Cu1—N8—C10—N9	174.1 (3)
C2—N3—C1—N1	0.4 (5)	C9—N9—C10—N8	0.1 (5)
C3—N3—C1—N1	−174.2 (4)	C11—N9—C10—N8	−171.1 (4)
N1—N2—C2—N3	0.4 (5)	C10—N9—C11—C12	62.3 (5)
Cu2—N2—C2—N3	179.8 (3)	C9—N9—C11—C12	−107.2 (4)
C1—N3—C2—N2	−0.4 (5)	Cu3^vi—O10—C12—O11	−13.8 (6)
C3—N3—C2—N2	174.0 (4)	Cu3^vi—O10—C12—C11	167.2 (2)
C2—N3—C3—C4	−110.0 (5)	N9—C11—C12—O11	1.7 (5)
C1—N3—C3—C4	63.4 (5)	N9—C11—C12—O10	−179.2 (3)
Cu2^iv—O6—C4—O7	−2.5 (5)

Symmetry codes: (i) x, y, z−1; (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, z+1; (vi) x, −y+1/2, z−1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O10^vii	0.85	2.01	2.811 (4)	156
O1W—H1W···O11	0.85	2.11	2.940 (5)	166
O1W—H2W···O4	0.85	1.93	2.767 (4)	168
O2W—H3W···O9^viii	0.85	1.95	2.798 (5)	178
O2W—H4W···O1W	0.85	2.00	2.812 (6)	159
C1—H1···O5^ix	0.94	2.58	3.346 (5)	139
C2—H2···O5^x	0.94	2.28	2.955 (5)	128
C5—H5···O3^xi	0.94	2.39	2.941 (5)	117
C6—H6···O2W^iii	0.94	2.30	3.176 (6)	154
C7—H7A···O3^xi	0.98	2.25	3.094 (6)	144
C7—H7B···O1W^iii	0.98	2.38	3.338 (5)	164
C9—H9···O7^xii	0.94	2.25	3.067 (6)	144

Symmetry codes: (iii) x, −y+1/2, z+1/2; (vii) −x+1, y−1/2, −z+1/2; (viii) −x+1, y+1/2, −z+3/2; (ix) −x, −y, −z; (x) −x, y−1/2, −z+1/2; (xi) −x, −y, −z+1; (xii) −x+1, y+1/2, −z+1/2.