A new one-dimensional Cu^II complex with a three-dimensional supra­molecular architecture incorporating benzene-1,3-di­carboxyl­ate and 1-[(1H-benzotriazol-1-yl)meth­yl]-1H-imidazole

Subtle modifications of N-donor ligands can result in complexes with very different compositions and architectures. In the complex catena-poly[[bis­{1-[(1H-benzotriazol-1-yl)meth­yl]-1H-imidazole-[kappa]N³}copper(II)]-[mu]-benzene-1,3-di­carboxyl­ato-[kappa]³O¹,O^1':O³], {[Cu(C₈H₄O₄)(C₁₀H₉N₅)₂(H₂O)]·2H₂O}_n, each Cu^II ion is six-coordinated by two N atoms from two crystallographically independent 1-[(1H-benzotriazol-1-yl)meth­yl]-1H-imidazole (bmi) ligands, by three O atoms from two symmetry-related benzene-1,3-di­carboxyl­ate (bdic^2-) ligands and by one water mol­ecule, leading to a distorted CuN₂O₄ octa­hedral coordination environment. The Cu^II ions are connected by bridging bdic^2- anions to generate a one-dimensional chain. The bmi ligands coordinate to the Cu^II ions in monodentate modes and are pendant on opposite sides of the main chain. In the crystal, the chains are linked by O-H...O and O-H...N hydrogen bonds, as well as by [pi]-[pi] inter­actions, into a three-dimensional network. A thermogravimetric analysis was carried out and the fluorescence behaviour of the complex was also investigated.

Computing details

Data collection: CrystalClear (Rigaku/MSC, 2004); cell refinement: CrystalClear (Rigaku/MSC, 2004); data reduction: CrystalClear (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: publCIF (Westrip, 2010).

catena-Poly[[bis{1-[(1H-benzotriazol-1-yl)methyl]-1H-1,3-imidazole-κN³}copper(II)]-µ-benzene-1,3-dicarboxylato-κ³O¹,O^1':O³]

Crystal data

[Cu(C8H4O4)(C10H9N5)2(H2O)]·2H2O	Z = 2
Mr = 680.14	F(000) = 702
Triclinic, P1	Dx = 1.524 Mg m^−3
a = 10.174 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.538 (3) Å	Cell parameters from 4516 reflections
c = 13.665 (3) Å	θ = 1.9–27.9°
α = 63.45 (3)°	µ = 0.80 mm^−1
β = 77.06 (3)°	T = 293 K
γ = 73.02 (3)°	Prism, blue
V = 1482.5 (7) Å^3	0.18 × 0.15 × 0.12 mm

Data collection

Rigaku Saturn diffractometer	5802 independent reflections
Radiation source: fine-focus sealed tube	4596 reflections with I > 2σ(I)
Detector resolution: 28.5714 pixels mm^-1	Rint = 0.040
ω scans	θmax = 26.0°, θmin = 2.1°
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2004)	h = −12→12
Tmin = 0.869, Tmax = 0.910	k = −15→15
13759 measured reflections	l = −16→15

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.060	H-atom parameters constrained
wR(F^2) = 0.148	w = 1/[σ^2(Fo^2) + (0.0708P)^2 + 0.7087P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
5802 reflections	Δρmax = 0.32 e Å^−3
415 parameters	Δρmin = −0.38 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	0.61160 (4)	0.51451 (4)	0.75427 (4)	0.03293 (16)
N1	0.6490 (3)	0.3776 (3)	0.7066 (3)	0.0350 (7)
N2	0.7383 (3)	0.2639 (3)	0.6135 (3)	0.0387 (7)
N3	0.9097 (4)	0.0941 (3)	0.5922 (3)	0.0482 (9)
N4	0.8460 (5)	−0.0029 (4)	0.6430 (3)	0.0628 (11)
N5	0.9391 (6)	−0.1023 (4)	0.6806 (4)	0.0734 (13)
N6	0.5758 (3)	0.6575 (3)	0.7924 (2)	0.0338 (7)
N7	0.4985 (3)	0.7864 (3)	0.8712 (3)	0.0353 (7)
N8	0.3329 (3)	0.9572 (3)	0.8948 (3)	0.0432 (8)
N9	0.3863 (4)	1.0591 (3)	0.8456 (3)	0.0610 (11)
N10	0.2872 (4)	1.1535 (3)	0.8013 (3)	0.0586 (10)
O1	0.8159 (2)	0.4973 (2)	0.7517 (2)	0.0349 (6)
O2	0.7436 (2)	0.3855 (2)	0.9238 (2)	0.0401 (6)
O3	1.3136 (3)	0.5510 (2)	0.6717 (2)	0.0465 (7)
O4	1.4237 (3)	0.4919 (3)	0.8185 (2)	0.0469 (7)
O5	0.5480 (3)	0.6575 (2)	0.5747 (2)	0.0516 (7)
H1W	0.6055	0.6489	0.5217	0.062*
H2W	0.4754	0.6362	0.5759	0.062*
O7	0.9522 (5)	0.5960 (5)	0.5384 (4)	0.1276 (18)
H5W	0.9949	0.5222	0.5697	0.153*
H6W	0.8972	0.6051	0.5924	0.153*
C1	0.8346 (3)	0.4340 (3)	0.8542 (3)	0.0313 (8)
C2	1.3212 (3)	0.5034 (3)	0.7728 (3)	0.0366 (9)
C3	0.9705 (3)	0.4192 (3)	0.8902 (3)	0.0307 (8)
C4	1.0791 (3)	0.4666 (3)	0.8153 (3)	0.0324 (8)
H4A	1.0685	0.5083	0.7407	0.039*
C5	1.2038 (3)	0.4517 (3)	0.8524 (3)	0.0327 (8)
C6	1.2179 (4)	0.3890 (3)	0.9636 (3)	0.0395 (9)
H6A	1.3010	0.3778	0.9885	0.047*
C7	1.1099 (4)	0.3423 (3)	1.0392 (3)	0.0413 (9)
H7A	1.1204	0.3006	1.1139	0.050*
C8	0.9867 (4)	0.3590 (3)	1.0014 (3)	0.0349 (8)
H8A	0.9138	0.3293	1.0515	0.042*
C9	0.7484 (4)	0.3575 (3)	0.6326 (3)	0.0375 (9)
H9A	0.8168	0.4021	0.5980	0.045*
C10	0.5720 (4)	0.2907 (3)	0.7367 (3)	0.0412 (9)
H10A	0.4947	0.2820	0.7887	0.049*
C11	0.6252 (4)	0.2214 (4)	0.6803 (4)	0.0453 (10)
H11A	0.5924	0.1571	0.6851	0.054*
C12	0.8283 (5)	0.2167 (4)	0.5360 (3)	0.0482 (10)
H12A	0.8901	0.2710	0.4908	0.058*
H12B	0.7726	0.2149	0.4879	0.058*
C13	1.0492 (5)	0.0515 (4)	0.5976 (3)	0.0530 (11)
C14	1.0656 (7)	−0.0733 (5)	0.6546 (4)	0.0689 (16)
C15	1.1968 (8)	−0.1479 (7)	0.6752 (5)	0.099 (3)
H15A	1.2082	−0.2321	0.7144	0.119*
C16	1.3063 (8)	−0.0960 (9)	0.6375 (7)	0.116 (3)
H16A	1.3944	−0.1453	0.6494	0.139*
C17	1.2907 (6)	0.0308 (9)	0.5804 (6)	0.103 (2)
H17A	1.3690	0.0637	0.5553	0.123*
C18	1.1600 (5)	0.1097 (5)	0.5601 (4)	0.0693 (14)
H18A	1.1482	0.1942	0.5244	0.083*
C19	0.4855 (3)	0.6825 (3)	0.8693 (3)	0.0315 (8)
H19A	0.4221	0.6358	0.9156	0.038*
C20	0.6513 (4)	0.7482 (3)	0.7442 (3)	0.0426 (9)
H20A	0.7232	0.7535	0.6877	0.051*
C21	0.6034 (4)	0.8272 (3)	0.7927 (3)	0.0434 (9)
H21A	0.6357	0.8962	0.7760	0.052*
C22	0.4225 (4)	0.8388 (3)	0.9492 (3)	0.0431 (9)
H22A	0.3670	0.7835	1.0048	0.052*
H22B	0.4874	0.8478	0.9857	0.052*
C23	0.1965 (4)	0.9868 (3)	0.8811 (3)	0.0374 (9)
C24	0.0958 (4)	0.9180 (3)	0.9148 (3)	0.0409 (9)
H24A	0.1161	0.8335	0.9536	0.049*
C25	−0.0344 (5)	0.9824 (4)	0.8874 (3)	0.0494 (10)
H25A	−0.1045	0.9402	0.9075	0.059*
C26	−0.0654 (5)	1.1096 (4)	0.8300 (3)	0.0513 (11)
H26A	−0.1559	1.1496	0.8148	0.062*
C27	0.0323 (5)	1.1766 (4)	0.7959 (3)	0.0504 (11)
H27A	0.0107	1.2610	0.7569	0.060*
C28	0.1675 (5)	1.1133 (3)	0.8218 (3)	0.0435 (10)
O6	0.7304 (3)	0.6158 (3)	0.4016 (2)	0.0551 (8)
H3W	0.7139	0.6838	0.3464	0.066*
H4W	0.7171	0.5571	0.3927	0.066*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0176 (2)	0.0419 (3)	0.0429 (3)	−0.00510 (17)	−0.00402 (18)	−0.0210 (2)
N1	0.0247 (16)	0.0396 (16)	0.0404 (18)	−0.0061 (13)	−0.0065 (13)	−0.0153 (14)
N2	0.0384 (19)	0.0379 (17)	0.0392 (18)	−0.0019 (14)	−0.0078 (15)	−0.0175 (14)
N3	0.054 (2)	0.049 (2)	0.041 (2)	−0.0012 (17)	−0.0043 (17)	−0.0236 (16)
N4	0.077 (3)	0.053 (2)	0.060 (3)	−0.015 (2)	−0.002 (2)	−0.026 (2)
N5	0.103 (4)	0.051 (2)	0.061 (3)	−0.005 (2)	−0.008 (3)	−0.027 (2)
N6	0.0246 (15)	0.0356 (16)	0.0395 (18)	−0.0069 (12)	−0.0063 (13)	−0.0124 (14)
N7	0.0312 (17)	0.0312 (15)	0.0394 (18)	−0.0024 (13)	−0.0046 (14)	−0.0134 (13)
N8	0.042 (2)	0.0306 (16)	0.053 (2)	−0.0100 (14)	0.0033 (16)	−0.0165 (15)
N9	0.051 (2)	0.042 (2)	0.081 (3)	−0.0171 (18)	0.011 (2)	−0.023 (2)
N10	0.056 (2)	0.0306 (18)	0.073 (3)	−0.0100 (17)	0.006 (2)	−0.0131 (17)
O1	0.0197 (12)	0.0446 (14)	0.0396 (15)	−0.0071 (10)	−0.0049 (11)	−0.0157 (12)
O2	0.0238 (13)	0.0505 (15)	0.0409 (15)	−0.0162 (12)	0.0013 (11)	−0.0117 (12)
O3	0.0281 (14)	0.0560 (17)	0.0495 (18)	−0.0137 (12)	−0.0024 (13)	−0.0146 (14)
O4	0.0186 (13)	0.0776 (19)	0.0615 (19)	−0.0153 (13)	0.0021 (12)	−0.0434 (16)
O5	0.0516 (18)	0.0569 (17)	0.0442 (17)	−0.0132 (14)	−0.0007 (14)	−0.0202 (14)
O7	0.114 (4)	0.156 (4)	0.102 (4)	−0.071 (4)	0.041 (3)	−0.042 (3)
C1	0.0203 (17)	0.0334 (18)	0.044 (2)	−0.0055 (14)	−0.0029 (16)	−0.0195 (17)
C2	0.0181 (17)	0.041 (2)	0.058 (3)	−0.0040 (15)	−0.0016 (17)	−0.0287 (19)
C3	0.0243 (18)	0.0305 (17)	0.039 (2)	−0.0056 (14)	−0.0053 (15)	−0.0147 (15)
C4	0.0245 (18)	0.0358 (18)	0.038 (2)	−0.0053 (14)	−0.0060 (15)	−0.0162 (16)
C5	0.0218 (17)	0.0323 (18)	0.049 (2)	−0.0045 (14)	−0.0042 (16)	−0.0222 (17)
C6	0.0257 (19)	0.041 (2)	0.055 (3)	−0.0036 (15)	−0.0161 (18)	−0.0194 (19)
C7	0.040 (2)	0.039 (2)	0.045 (2)	−0.0115 (17)	−0.0136 (18)	−0.0114 (17)
C8	0.0298 (19)	0.0344 (18)	0.042 (2)	−0.0100 (15)	−0.0029 (16)	−0.0151 (16)
C9	0.031 (2)	0.0352 (19)	0.040 (2)	−0.0081 (15)	−0.0039 (17)	−0.0093 (17)
C10	0.028 (2)	0.041 (2)	0.055 (3)	−0.0097 (16)	−0.0042 (18)	−0.0190 (19)
C11	0.036 (2)	0.045 (2)	0.064 (3)	−0.0109 (18)	−0.007 (2)	−0.028 (2)
C12	0.057 (3)	0.046 (2)	0.038 (2)	−0.002 (2)	−0.007 (2)	−0.0196 (19)
C13	0.060 (3)	0.059 (3)	0.040 (2)	0.005 (2)	−0.008 (2)	−0.030 (2)
C14	0.093 (4)	0.061 (3)	0.041 (3)	0.020 (3)	−0.013 (3)	−0.031 (2)
C15	0.109 (6)	0.111 (5)	0.059 (4)	0.054 (4)	−0.037 (4)	−0.053 (4)
C16	0.091 (6)	0.159 (8)	0.090 (5)	0.058 (5)	−0.044 (5)	−0.082 (6)
C17	0.057 (4)	0.185 (8)	0.088 (5)	−0.005 (4)	−0.008 (3)	−0.088 (5)
C18	0.055 (3)	0.096 (4)	0.063 (3)	−0.005 (3)	−0.006 (3)	−0.045 (3)
C19	0.0243 (18)	0.0318 (18)	0.035 (2)	−0.0068 (14)	−0.0054 (15)	−0.0093 (15)
C20	0.034 (2)	0.043 (2)	0.043 (2)	−0.0102 (17)	0.0038 (18)	−0.0131 (18)
C21	0.038 (2)	0.038 (2)	0.051 (2)	−0.0128 (17)	−0.0001 (19)	−0.0144 (19)
C22	0.049 (2)	0.035 (2)	0.043 (2)	−0.0037 (17)	−0.0064 (19)	−0.0167 (17)
C23	0.045 (2)	0.0341 (19)	0.032 (2)	−0.0078 (16)	0.0037 (17)	−0.0161 (16)
C24	0.048 (2)	0.039 (2)	0.039 (2)	−0.0109 (18)	−0.0052 (18)	−0.0172 (17)
C25	0.053 (3)	0.059 (3)	0.045 (2)	−0.018 (2)	−0.005 (2)	−0.027 (2)
C26	0.052 (3)	0.059 (3)	0.038 (2)	0.003 (2)	−0.014 (2)	−0.021 (2)
C27	0.061 (3)	0.039 (2)	0.039 (2)	0.001 (2)	−0.003 (2)	−0.0140 (18)
C28	0.054 (3)	0.033 (2)	0.038 (2)	−0.0103 (18)	0.0055 (19)	−0.0142 (17)
O6	0.061 (2)	0.0498 (17)	0.0498 (18)	−0.0127 (14)	−0.0056 (15)	−0.0163 (14)

Geometric parameters (Å, º)

Cu1—O4^i	1.962 (3)	C5—C6	1.382 (5)
Cu1—N6	1.997 (3)	C6—C7	1.395 (5)
Cu1—N1	2.006 (3)	C6—H6A	0.9300
Cu1—O1	2.020 (2)	C7—C8	1.386 (5)
Cu1—O5	2.399 (3)	C7—H7A	0.9300
N1—C9	1.315 (5)	C8—H8A	0.9300
N1—C10	1.387 (4)	C9—H9A	0.9300
N2—C9	1.346 (5)	C10—C11	1.335 (6)
N2—C11	1.376 (5)	C10—H10A	0.9300
N2—C12	1.456 (5)	C11—H11A	0.9300
N3—C13	1.369 (6)	C12—H12A	0.9700
N3—N4	1.374 (5)	C12—H12B	0.9700
N3—C12	1.457 (5)	C13—C14	1.378 (6)
N4—N5	1.293 (6)	C13—C18	1.398 (7)
N5—C14	1.366 (7)	C14—C15	1.393 (8)
N6—C19	1.320 (5)	C15—C16	1.340 (10)
N6—C20	1.389 (5)	C15—H15A	0.9300
N7—C19	1.359 (4)	C16—C17	1.400 (10)
N7—C21	1.367 (5)	C16—H16A	0.9300
N7—C22	1.458 (5)	C17—C18	1.405 (8)
N8—C23	1.361 (5)	C17—H17A	0.9300
N8—N9	1.362 (4)	C18—H18A	0.9300
N8—C22	1.454 (5)	C19—H19A	0.9300
N9—N10	1.311 (5)	C20—C21	1.349 (5)
N10—C28	1.376 (5)	C20—H20A	0.9300
O1—C1	1.290 (4)	C21—H21A	0.9300
O2—C1	1.244 (4)	C22—H22A	0.9700
O3—C2	1.247 (5)	C22—H22B	0.9700
O4—C2	1.274 (4)	C23—C28	1.395 (5)
O4—Cu1^ii	1.962 (3)	C23—C24	1.398 (5)
O5—H1W	0.8500	C24—C25	1.369 (6)
O5—H2W	0.8499	C24—H24A	0.9300
O7—H5W	0.8500	C25—C26	1.399 (6)
O7—H6W	0.8501	C25—H25A	0.9300
C1—C3	1.504 (5)	C26—C27	1.357 (6)
C2—C5	1.507 (5)	C26—H26A	0.9300
C3—C8	1.386 (5)	C27—C28	1.406 (6)
C3—C4	1.398 (5)	C27—H27A	0.9300
C4—C5	1.403 (5)	O6—H3W	0.8500
C4—H4A	0.9300	O6—H4W	0.8499
O4^i—Cu1—N6	89.75 (12)	C11—C10—N1	110.0 (4)
O4^i—Cu1—N1	91.80 (12)	C11—C10—H10A	125.0
N6—Cu1—N1	176.62 (12)	N1—C10—H10A	125.0
O4^i—Cu1—O1	157.13 (11)	C10—C11—N2	106.4 (3)
N6—Cu1—O1	88.35 (11)	C10—C11—H11A	126.8
N1—Cu1—O1	91.38 (11)	N2—C11—H11A	126.8
O4^i—Cu1—O5	95.31 (12)	N2—C12—N3	111.8 (3)
N6—Cu1—O5	87.41 (11)	N2—C12—H12A	109.3
N1—Cu1—O5	89.46 (11)	N3—C12—H12A	109.3
O1—Cu1—O5	107.36 (11)	N2—C12—H12B	109.3
C9—N1—C10	105.3 (3)	N3—C12—H12B	109.3
C9—N1—Cu1	126.2 (3)	H12A—C12—H12B	107.9
C10—N1—Cu1	128.3 (3)	N3—C13—C14	104.4 (5)
C9—N2—C11	107.1 (3)	N3—C13—C18	132.8 (4)
C9—N2—C12	126.9 (3)	C14—C13—C18	122.8 (5)
C11—N2—C12	126.0 (3)	N5—C14—C13	109.1 (5)
C13—N3—N4	109.2 (4)	N5—C14—C15	130.6 (6)
C13—N3—C12	131.1 (4)	C13—C14—C15	120.3 (7)
N4—N3—C12	119.5 (4)	C16—C15—C14	118.7 (7)
N5—N4—N3	108.5 (4)	C16—C15—H15A	120.6
N4—N5—C14	108.8 (4)	C14—C15—H15A	120.6
C19—N6—C20	106.5 (3)	C15—C16—C17	121.4 (7)
C19—N6—Cu1	128.8 (2)	C15—C16—H16A	119.3
C20—N6—Cu1	124.6 (3)	C17—C16—H16A	119.3
C19—N7—C21	107.7 (3)	C16—C17—C18	121.8 (7)
C19—N7—C22	126.0 (3)	C16—C17—H17A	119.1
C21—N7—C22	126.1 (3)	C18—C17—H17A	119.1
C23—N8—N9	110.4 (3)	C13—C18—C17	114.9 (6)
C23—N8—C22	130.1 (3)	C13—C18—H18A	122.6
N9—N8—C22	119.5 (3)	C17—C18—H18A	122.6
N10—N9—N8	108.3 (4)	N6—C19—N7	110.1 (3)
N9—N10—C28	108.6 (3)	N6—C19—H19A	125.0
C1—O1—Cu1	102.2 (2)	N7—C19—H19A	125.0
C2—O4—Cu1^ii	130.1 (3)	C21—C20—N6	108.9 (3)
Cu1—O5—H1W	114.8	C21—C20—H20A	125.6
Cu1—O5—H2W	99.4	N6—C20—H20A	125.6
H1W—O5—H2W	108.6	C20—C21—N7	106.9 (3)
H5W—O7—H6W	100.7	C20—C21—H21A	126.6
O2—C1—O1	122.0 (3)	N7—C21—H21A	126.6
O2—C1—C3	119.3 (3)	N8—C22—N7	111.6 (3)
O1—C1—C3	118.7 (3)	N8—C22—H22A	109.3
O3—C2—O4	125.5 (3)	N7—C22—H22A	109.3
O3—C2—C5	120.4 (3)	N8—C22—H22B	109.3
O4—C2—C5	114.1 (4)	N7—C22—H22B	109.3
C8—C3—C4	119.3 (3)	H22A—C22—H22B	108.0
C8—C3—C1	118.7 (3)	N8—C23—C28	104.4 (3)
C4—C3—C1	122.0 (3)	N8—C23—C24	133.2 (3)
C3—C4—C5	120.2 (3)	C28—C23—C24	122.4 (4)
C3—C4—H4A	119.9	C25—C24—C23	116.1 (4)
C5—C4—H4A	119.9	C25—C24—H24A	122.0
C6—C5—C4	119.1 (3)	C23—C24—H24A	122.0
C6—C5—C2	120.1 (3)	C24—C25—C26	122.0 (4)
C4—C5—C2	120.8 (3)	C24—C25—H25A	119.0
C5—C6—C7	121.2 (3)	C26—C25—H25A	119.0
C5—C6—H6A	119.4	C27—C26—C25	122.1 (4)
C7—C6—H6A	119.4	C27—C26—H26A	118.9
C8—C7—C6	119.0 (4)	C25—C26—H26A	118.9
C8—C7—H7A	120.5	C26—C27—C28	117.4 (4)
C6—C7—H7A	120.5	C26—C27—H27A	121.3
C3—C8—C7	121.1 (3)	C28—C27—H27A	121.3
C3—C8—H8A	119.4	N10—C28—C23	108.4 (4)
C7—C8—H8A	119.4	N10—C28—C27	131.6 (4)
N1—C9—N2	111.2 (3)	C23—C28—C27	120.0 (4)
N1—C9—H9A	124.4	H3W—O6—H4W	112.9
N2—C9—H9A	124.4
C13—N3—N4—N5	0.9 (5)	C12—N3—C13—C18	6.1 (8)
C12—N3—N4—N5	175.8 (4)	N4—N5—C14—C13	0.0 (5)
N3—N4—N5—C14	−0.5 (5)	N4—N5—C14—C15	−178.8 (5)
C23—N8—N9—N10	0.5 (5)	N3—C13—C14—N5	0.6 (5)
C22—N8—N9—N10	179.1 (4)	C18—C13—C14—N5	179.6 (4)
N8—N9—N10—C28	0.1 (5)	N3—C13—C14—C15	179.5 (4)
Cu1—O1—C1—O2	10.0 (4)	C18—C13—C14—C15	−1.4 (7)
Cu1—O1—C1—C3	−169.7 (2)	N5—C14—C15—C16	177.9 (6)
Cu1^ii—O4—C2—O3	−11.9 (6)	C13—C14—C15—C16	−0.8 (8)
Cu1^ii—O4—C2—C5	167.2 (2)	C14—C15—C16—C17	1.4 (10)
O2—C1—C3—C8	−4.5 (5)	C15—C16—C17—C18	0.1 (10)
O1—C1—C3—C8	175.3 (3)	N3—C13—C18—C17	−178.5 (5)
O2—C1—C3—C4	177.0 (3)	C14—C13—C18—C17	2.8 (7)
O1—C1—C3—C4	−3.2 (5)	C16—C17—C18—C13	−2.1 (8)
C8—C3—C4—C5	1.0 (5)	C20—N6—C19—N7	1.0 (4)
C1—C3—C4—C5	179.5 (3)	Cu1—N6—C19—N7	177.4 (2)
C3—C4—C5—C6	0.4 (5)	C21—N7—C19—N6	−0.9 (4)
C3—C4—C5—C2	−179.4 (3)	C22—N7—C19—N6	−176.0 (3)
O3—C2—C5—C6	174.0 (3)	C19—N6—C20—C21	−0.6 (4)
O4—C2—C5—C6	−5.2 (5)	Cu1—N6—C20—C21	−177.3 (3)
O3—C2—C5—C4	−6.3 (5)	N6—C20—C21—N7	0.1 (4)
O4—C2—C5—C4	174.5 (3)	C19—N7—C21—C20	0.5 (4)
C4—C5—C6—C7	−1.0 (5)	C22—N7—C21—C20	175.6 (3)
C2—C5—C6—C7	178.8 (3)	C23—N8—C22—N7	94.9 (5)
C5—C6—C7—C8	0.3 (6)	N9—N8—C22—N7	−83.4 (4)
C4—C3—C8—C7	−1.7 (5)	C19—N7—C22—N8	−115.3 (4)
C1—C3—C8—C7	179.7 (3)	C21—N7—C22—N8	70.4 (5)
C6—C7—C8—C3	1.1 (6)	N9—N8—C23—C28	−0.9 (4)
C10—N1—C9—N2	0.5 (4)	C22—N8—C23—C28	−179.2 (4)
Cu1—N1—C9—N2	−175.1 (2)	N9—N8—C23—C24	−179.9 (4)
C11—N2—C9—N1	−0.4 (4)	C22—N8—C23—C24	1.8 (7)
C12—N2—C9—N1	179.0 (3)	N8—C23—C24—C25	178.1 (4)
C9—N1—C10—C11	−0.5 (4)	C28—C23—C24—C25	−0.8 (6)
Cu1—N1—C10—C11	175.0 (3)	C23—C24—C25—C26	−0.7 (6)
N1—C10—C11—N2	0.3 (4)	C24—C25—C26—C27	1.6 (6)
C9—N2—C11—C10	0.0 (4)	C25—C26—C27—C28	−0.9 (6)
C12—N2—C11—C10	−179.4 (3)	N9—N10—C28—C23	−0.7 (5)
C9—N2—C12—N3	112.3 (4)	N9—N10—C28—C27	177.8 (4)
C11—N2—C12—N3	−68.4 (5)	N8—C23—C28—N10	0.9 (4)
C13—N3—C12—N2	−114.4 (5)	C24—C23—C28—N10	−179.9 (4)
N4—N3—C12—N2	72.0 (5)	N8—C23—C28—C27	−177.7 (4)
N4—N3—C13—C14	−0.9 (4)	C24—C23—C28—C27	1.4 (6)
C12—N3—C13—C14	−175.0 (4)	C26—C27—C28—N10	−178.8 (4)
N4—N3—C13—C18	−179.8 (5)	C26—C27—C28—C23	−0.5 (6)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H1W···O6	0.85	1.96	2.808 (4)	174
O7—H6W···O1	0.85	2.11	2.814 (5)	139
O5—H2W···O3^i	0.85	2.09	2.844 (4)	147
O7—H5W···O7^iii	0.85	2.41	2.876 (11)	115
O6—H3W···N10^iv	0.85	2.13	2.973 (5)	169
O6—H4W···O3^iii	0.85	2.04	2.864 (4)	165

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