Bis[4-amino-3,5-bis-(pyridin-2-yl)-4H-1,2,4-triazole-κN,N]bis-(benzene-1,2-dicarb-oxy-lic acid-κO)copper(II) bis-(2-carb-oxy-benzoate).

In the complex cation of the title salt, [Cu(C(12)H(10)N(6))(2)(C(8)H(6)O(4))(2)](C(8)H(5)O(4))(2), the Cu(II) atom, lying on an inversion center, exhibits a distorted octa-hedral geometry defined by four N atoms from two 4-amino-3,5-bis-(pyridin-2-yl)-4H-1,2,4-triazole ligands in the equatorial plane and two axial O atoms from two benzene-1,2-dicarb-oxy-lic acid ligands. In the crystal, the complex cations and the monodeprotonated 2-carb-oxy-benzoate anions are connected by O-H⋯O and N-H⋯O hydrogen bonds, forming a tape along [100]. Adjacent tapes are further linked into a three-dimensional arrangement via π-π stacking inter-actions between the triazole and benzene rings and between the pyridine and benzene rings [centroid-centroid distances = 3.6734 (14)/3.9430 (16) and 3.8221 (14) Å]. Intra-molecular N-H⋯N and O-H⋯O hydrogen bonds are also observed.

Related literature

For the coordination systems of triazole derivatives, see: Chen et al. (2011 ▶); Li et al. (2010 ▶); Zhang et al. (2011 ▶). For the coordination systems of aromatic polycarboxyl­ate ligands, see: Sun et al. (2004 ▶); Zehnder et al. (2011 ▶). For the coordination systems of mixed ligands, see: Du et al. (2005 ▶, 2006 ▶, 2007 ▶, 2008 ▶); Habib et al. (2009 ▶).

Experimental

Crystal data

[Cu(C12H10N6)2(C8H6O4)2](C8H5O4)2

M = 1202.56

Monoclinic,

a = 12.1171 (7) Å

b = 15.9875 (10) Å

c = 15.7498 (7) Å

β = 121.739 (3)°

V = 2594.8 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.51 mm−1

T = 294 K

0.24 × 0.23 × 0.20 mm

Data collection

Bruker APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.885, T max = 0.906

13987 measured reflections

4579 independent reflections

3594 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.098

S = 1.05

4579 reflections

388 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.38 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812000128/hy2503sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812000128/hy2503Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Cu(C12H10N6)2(C8H6O4)2](C8H5O4)2	F(000) = 1238
Mr = 1202.56	Dx = 1.539 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4780 reflections
a = 12.1171 (7) Å	θ = 2.2–25.4°
b = 15.9875 (10) Å	µ = 0.51 mm−1
c = 15.7498 (7) Å	T = 294 K
β = 121.739 (3)°	Block, blue
V = 2594.8 (2) Å3	0.24 × 0.23 × 0.20 mm
Z = 2

Bruker APEX CCD diffractometer	4579 independent reflections
Radiation source: fine-focus sealed tube	3594 reflections with I > 2σ(I)
graphite	Rint = 0.023
φ and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→9
Tmin = 0.885, Tmax = 0.906	k = −18→19
13987 measured reflections	l = −18→18

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.051P)2 + 0.7095P] where P = (Fo2 + 2Fc2)/3
4579 reflections	(Δ/σ)max = 0.001
388 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.38 e Å−3

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.

	x	y	z	Uiso*/Ueq
Cu1	0.0000	0.5000	0.5000	0.03702 (13)
O5	0.25819 (17)	0.25012 (10)	0.25335 (15)	0.0578 (5)
O6	0.42188 (18)	0.33760 (10)	0.30636 (14)	0.0557 (5)
O7	0.61160 (19)	0.35032 (10)	0.29636 (15)	0.0582 (5)
H7	0.5561	0.3418	0.3103	0.087*
O8	0.71299 (18)	0.27995 (10)	0.23886 (15)	0.0612 (5)
N1	0.11634 (16)	0.58006 (11)	0.48080 (13)	0.0357 (4)
N2	0.12225 (17)	0.41813 (11)	0.49978 (14)	0.0384 (4)
N3	0.14291 (17)	0.33373 (11)	0.51187 (14)	0.0398 (4)
N4	0.28569 (17)	0.39093 (11)	0.48400 (13)	0.0364 (4)
N5	0.38715 (19)	0.40434 (13)	0.46593 (16)	0.0509 (5)
H5A	0.3530	0.3915	0.4012	0.076*
H5B	0.4406	0.3643	0.5075	0.076*
N6	0.4013 (2)	0.22776 (13)	0.50357 (16)	0.0519 (5)
C1	0.2106 (2)	0.54244 (14)	0.47258 (16)	0.0358 (5)
C2	0.1071 (2)	0.66321 (14)	0.47397 (18)	0.0430 (5)
H2A	0.0436	0.6896	0.4805	0.052*
C3	0.1889 (2)	0.71151 (15)	0.45752 (19)	0.0500 (6)
H3A	0.1800	0.7694	0.4528	0.060*
C4	0.2829 (2)	0.67294 (15)	0.4483 (2)	0.0511 (6)
H4	0.3383	0.7044	0.4368	0.061*
C5	0.2950 (2)	0.58683 (15)	0.45617 (18)	0.0451 (6)
H5	0.3587	0.5596	0.4505	0.054*
C6	0.2094 (2)	0.45237 (13)	0.48423 (15)	0.0346 (5)
C7	0.2428 (2)	0.31780 (14)	0.50288 (16)	0.0374 (5)
C8	0.3001 (2)	0.23437 (14)	0.51511 (16)	0.0398 (5)
C9	0.4507 (3)	0.15095 (18)	0.5139 (2)	0.0652 (8)
H9	0.5203	0.1444	0.5051	0.078*
C10	0.4054 (3)	0.08162 (18)	0.5366 (2)	0.0683 (8)
H10	0.4430	0.0296	0.5426	0.082*
C11	0.3039 (3)	0.09019 (17)	0.5503 (2)	0.0629 (7)
H11	0.2719	0.0440	0.5665	0.075*
C12	0.2495 (2)	0.16788 (15)	0.53986 (18)	0.0488 (6)
H12	0.1806	0.1755	0.5492	0.059*
C21	0.4445 (2)	0.19723 (13)	0.26040 (16)	0.0360 (5)
C22	0.5573 (2)	0.20464 (13)	0.25486 (16)	0.0365 (5)
C23	0.6072 (2)	0.13201 (14)	0.23817 (19)	0.0465 (6)
H23	0.6802	0.1362	0.2332	0.056*
C24	0.5527 (3)	0.05483 (15)	0.2289 (2)	0.0536 (7)
H24	0.5893	0.0076	0.2188	0.064*
C25	0.4435 (2)	0.04748 (14)	0.2345 (2)	0.0526 (7)
H25	0.4056	−0.0046	0.2282	0.063*
C26	0.3915 (2)	0.11756 (14)	0.24943 (19)	0.0461 (6)
H26	0.3172	0.1119	0.2525	0.055*
C27	0.3693 (2)	0.26633 (14)	0.27388 (17)	0.0420 (5)
C28	0.6319 (2)	0.28304 (14)	0.26291 (18)	0.0423 (5)
O1	0.14046 (17)	0.52179 (11)	0.68003 (12)	0.0519 (4)
O2	0.15757 (19)	0.60865 (11)	0.79643 (15)	0.0611 (5)
H2	0.2051	0.6341	0.7829	0.092*
O3	−0.12352 (19)	0.62542 (11)	0.74566 (13)	0.0596 (5)
H3	−0.1594	0.6665	0.7517	0.089*
O4	−0.0100 (2)	0.62734 (12)	0.91204 (14)	0.0656 (5)
C13	0.0569 (2)	0.47914 (14)	0.78016 (16)	0.0375 (5)
C14	0.0682 (2)	0.39419 (15)	0.76748 (17)	0.0450 (6)
H14	0.1108	0.3770	0.7356	0.054*
C15	0.0174 (2)	0.33481 (15)	0.8014 (2)	0.0543 (7)
H15	0.0240	0.2782	0.7910	0.065*
C16	−0.0429 (3)	0.35987 (16)	0.8505 (2)	0.0555 (7)
H16	−0.0748	0.3201	0.8752	0.067*
C17	−0.0561 (2)	0.44334 (16)	0.86325 (18)	0.0502 (6)
H17A	−0.0970	0.4595	0.8967	0.060*
C18	−0.0091 (2)	0.50426 (14)	0.82691 (17)	0.0391 (5)
C19	0.1203 (2)	0.53840 (15)	0.74604 (17)	0.0407 (5)
C20	−0.0436 (2)	0.59263 (15)	0.83447 (18)	0.0436 (6)

	U11	U22	U33	U12	U13	U23
Cu1	0.0356 (2)	0.0354 (2)	0.0541 (2)	0.00117 (16)	0.03318 (19)	0.00233 (17)
O5	0.0499 (11)	0.0419 (10)	0.0929 (13)	0.0050 (8)	0.0454 (10)	0.0014 (9)
O6	0.0716 (12)	0.0328 (9)	0.0875 (13)	−0.0053 (8)	0.0589 (11)	−0.0126 (9)
O7	0.0693 (12)	0.0329 (9)	0.0952 (14)	−0.0116 (8)	0.0589 (12)	−0.0105 (9)
O8	0.0668 (12)	0.0412 (10)	0.1046 (15)	−0.0081 (9)	0.0650 (12)	−0.0038 (9)
N1	0.0327 (10)	0.0386 (11)	0.0434 (10)	0.0011 (8)	0.0253 (9)	0.0018 (8)
N2	0.0353 (10)	0.0378 (10)	0.0512 (11)	0.0023 (8)	0.0290 (9)	0.0039 (8)
N3	0.0385 (10)	0.0367 (10)	0.0531 (11)	0.0022 (8)	0.0302 (10)	0.0019 (9)
N4	0.0326 (10)	0.0420 (11)	0.0438 (10)	0.0018 (8)	0.0266 (9)	−0.0004 (8)
N5	0.0474 (12)	0.0530 (12)	0.0759 (14)	−0.0009 (10)	0.0488 (12)	0.0003 (10)
N6	0.0527 (13)	0.0478 (12)	0.0694 (14)	0.0089 (10)	0.0420 (12)	0.0006 (10)
C1	0.0326 (12)	0.0397 (13)	0.0394 (12)	0.0002 (10)	0.0217 (10)	0.0010 (10)
C2	0.0412 (13)	0.0392 (13)	0.0590 (15)	0.0013 (10)	0.0334 (12)	0.0022 (11)
C3	0.0500 (15)	0.0397 (13)	0.0692 (16)	0.0008 (11)	0.0374 (14)	0.0058 (12)
C4	0.0476 (14)	0.0478 (15)	0.0722 (17)	−0.0042 (12)	0.0412 (14)	0.0073 (13)
C5	0.0406 (13)	0.0450 (14)	0.0670 (16)	0.0012 (11)	0.0400 (13)	0.0047 (12)
C6	0.0295 (11)	0.0416 (13)	0.0396 (12)	−0.0012 (10)	0.0228 (10)	−0.0013 (10)
C7	0.0360 (12)	0.0396 (12)	0.0419 (12)	0.0001 (10)	0.0242 (11)	−0.0011 (10)
C8	0.0376 (12)	0.0438 (13)	0.0396 (12)	0.0040 (10)	0.0215 (11)	−0.0015 (10)
C9	0.0694 (19)	0.0571 (18)	0.088 (2)	0.0191 (15)	0.0542 (18)	0.0044 (15)
C10	0.082 (2)	0.0498 (17)	0.087 (2)	0.0219 (15)	0.0544 (19)	0.0071 (15)
C11	0.079 (2)	0.0455 (15)	0.0756 (19)	0.0079 (14)	0.0483 (17)	0.0111 (13)
C12	0.0495 (15)	0.0489 (15)	0.0549 (15)	0.0031 (12)	0.0321 (13)	0.0028 (12)
C21	0.0402 (12)	0.0276 (11)	0.0426 (12)	0.0021 (9)	0.0234 (11)	0.0029 (9)
C22	0.0380 (12)	0.0288 (11)	0.0436 (12)	−0.0004 (9)	0.0221 (11)	0.0020 (9)
C23	0.0468 (14)	0.0352 (13)	0.0672 (16)	0.0046 (10)	0.0367 (13)	0.0010 (11)
C24	0.0622 (17)	0.0297 (13)	0.0766 (18)	0.0053 (11)	0.0419 (15)	−0.0036 (12)
C25	0.0564 (16)	0.0271 (13)	0.0743 (18)	−0.0044 (11)	0.0343 (14)	−0.0003 (11)
C26	0.0437 (13)	0.0352 (13)	0.0643 (15)	−0.0031 (10)	0.0319 (13)	0.0034 (11)
C27	0.0507 (15)	0.0343 (13)	0.0522 (14)	0.0052 (11)	0.0348 (13)	0.0059 (10)
C28	0.0449 (14)	0.0310 (12)	0.0563 (14)	0.0010 (10)	0.0303 (12)	0.0033 (10)
O1	0.0536 (10)	0.0640 (11)	0.0518 (10)	−0.0052 (8)	0.0372 (9)	−0.0058 (8)
O2	0.0810 (14)	0.0491 (11)	0.0853 (13)	−0.0210 (9)	0.0657 (12)	−0.0156 (10)
O3	0.0661 (12)	0.0499 (11)	0.0610 (11)	0.0186 (9)	0.0321 (10)	0.0014 (9)
O4	0.0877 (14)	0.0598 (12)	0.0613 (12)	0.0002 (10)	0.0474 (11)	−0.0125 (9)
C13	0.0330 (12)	0.0390 (12)	0.0415 (12)	−0.0002 (9)	0.0203 (10)	−0.0006 (10)
C14	0.0412 (13)	0.0446 (14)	0.0500 (14)	0.0053 (11)	0.0245 (12)	−0.0034 (11)
C15	0.0547 (16)	0.0355 (13)	0.0653 (16)	0.0005 (12)	0.0265 (14)	0.0019 (12)
C16	0.0521 (16)	0.0465 (15)	0.0695 (17)	−0.0066 (12)	0.0330 (15)	0.0106 (13)
C17	0.0472 (14)	0.0558 (16)	0.0591 (15)	−0.0019 (12)	0.0358 (13)	0.0038 (12)
C18	0.0361 (12)	0.0405 (13)	0.0437 (12)	−0.0006 (10)	0.0230 (11)	−0.0001 (10)
C19	0.0359 (12)	0.0426 (13)	0.0463 (13)	0.0021 (10)	0.0236 (11)	−0.0014 (11)
C20	0.0437 (14)	0.0451 (13)	0.0544 (15)	−0.0036 (11)	0.0343 (13)	−0.0008 (12)

Cu1—N2	1.9781 (17)	C10—H10	0.9300
Cu1—N1	2.0409 (17)	C11—C12	1.375 (4)
Cu1—O1	2.4455 (17)	C11—H11	0.9300
O5—C27	1.236 (3)	C12—H12	0.9300
O6—C27	1.274 (3)	C21—C26	1.396 (3)
O7—C28	1.277 (3)	C21—C22	1.419 (3)
O7—H7	0.8200	C21—C27	1.516 (3)
O8—C28	1.226 (3)	C22—C23	1.397 (3)
N1—C2	1.334 (3)	C22—C28	1.511 (3)
N1—C1	1.356 (3)	C23—C24	1.371 (3)
N2—C6	1.322 (3)	C23—H23	0.9300
N2—N3	1.367 (3)	C24—C25	1.376 (3)
N3—C7	1.315 (3)	C24—H24	0.9300
N4—C6	1.350 (3)	C25—C26	1.365 (3)
N4—C7	1.374 (3)	C25—H25	0.9300
N4—N5	1.416 (2)	C26—H26	0.9300
N5—H5A	0.9001	O1—C19	1.216 (3)
N5—H5B	0.9014	O2—C19	1.311 (3)
N6—C8	1.334 (3)	O2—H2	0.8200
N6—C9	1.338 (3)	O3—C20	1.321 (3)
C1—C5	1.377 (3)	O3—H3	0.8200
C1—C6	1.453 (3)	O4—C20	1.201 (3)
C2—C3	1.384 (3)	C13—C14	1.390 (3)
C2—H2A	0.9300	C13—C18	1.401 (3)
C3—C4	1.369 (3)	C13—C19	1.487 (3)
C3—H3A	0.9300	C14—C15	1.382 (3)
C4—C5	1.383 (3)	C14—H14	0.9300
C4—H4	0.9300	C15—C16	1.373 (4)
C5—H5	0.9300	C15—H15	0.9300
C7—C8	1.469 (3)	C16—C17	1.371 (4)
C8—C12	1.382 (3)	C16—H16	0.9300
C9—C10	1.365 (4)	C17—C18	1.394 (3)
C9—H9	0.9300	C17—H17A	0.9300
C10—C11	1.362 (4)	C18—C20	1.496 (3)
N2—Cu1—N2i	180.0	C10—C11—H11	120.4
N2—Cu1—N1i	99.29 (7)	C12—C11—H11	120.4
N2i—Cu1—N1i	80.71 (7)	C11—C12—C8	118.2 (2)
N2—Cu1—N1	80.71 (7)	C11—C12—H12	120.9
N2i—Cu1—N1	99.29 (7)	C8—C12—H12	120.9
N1i—Cu1—N1	180.00 (8)	C26—C21—C22	117.6 (2)
N2—Cu1—O1	91.79 (7)	C26—C21—C27	114.24 (19)
N2i—Cu1—O1	88.21 (7)	C22—C21—C27	128.08 (19)
N1i—Cu1—O1	91.79 (6)	C23—C22—C21	117.9 (2)
N1—Cu1—O1	88.21 (6)	C23—C22—C28	113.98 (19)
C28—O7—H7	109.5	C21—C22—C28	128.06 (19)
C2—N1—C1	118.25 (18)	C24—C23—C22	122.4 (2)
C2—N1—Cu1	127.02 (15)	C24—C23—H23	118.8
C1—N1—Cu1	114.72 (14)	C22—C23—H23	118.8
C6—N2—N3	109.19 (17)	C23—C24—C25	119.7 (2)
C6—N2—Cu1	113.48 (14)	C23—C24—H24	120.1
N3—N2—Cu1	137.33 (14)	C25—C24—H24	120.1
C7—N3—N2	106.71 (18)	C26—C25—C24	119.2 (2)
C6—N4—C7	106.33 (17)	C26—C25—H25	120.4
C6—N4—N5	123.92 (18)	C24—C25—H25	120.4
C7—N4—N5	129.74 (18)	C25—C26—C21	123.1 (2)
N4—N5—H5A	105.3	C25—C26—H26	118.5
N4—N5—H5B	96.6	C21—C26—H26	118.5
H5A—N5—H5B	112.8	O5—C27—O6	122.6 (2)
C8—N6—C9	116.1 (2)	O5—C27—C21	117.6 (2)
N1—C1—C5	122.4 (2)	O6—C27—C21	119.8 (2)
N1—C1—C6	111.28 (18)	O8—C28—O7	121.4 (2)
C5—C1—C6	126.3 (2)	O8—C28—C22	118.8 (2)
N1—C2—C3	122.3 (2)	O7—C28—C22	119.8 (2)
N1—C2—H2A	118.9	C19—O1—Cu1	133.81 (16)
C3—C2—H2A	118.9	C19—O2—H2	109.5
C4—C3—C2	119.1 (2)	C20—O3—H3	109.5
C4—C3—H3A	120.5	C14—C13—C18	118.9 (2)
C2—C3—H3A	120.5	C14—C13—C19	117.5 (2)
C3—C4—C5	119.6 (2)	C18—C13—C19	123.6 (2)
C3—C4—H4	120.2	C15—C14—C13	121.2 (2)
C5—C4—H4	120.2	C15—C14—H14	119.4
C1—C5—C4	118.4 (2)	C13—C14—H14	119.4
C1—C5—H5	120.8	C16—C15—C14	119.6 (2)
C4—C5—H5	120.8	C16—C15—H15	120.2
N2—C6—N4	108.30 (18)	C14—C15—H15	120.2
N2—C6—C1	119.71 (18)	C17—C16—C15	120.3 (2)
N4—C6—C1	131.98 (19)	C17—C16—H16	119.9
N3—C7—N4	109.44 (19)	C15—C16—H16	119.9
N3—C7—C8	124.1 (2)	C16—C17—C18	121.0 (2)
N4—C7—C8	126.45 (19)	C16—C17—H17A	119.5
N6—C8—C12	123.6 (2)	C18—C17—H17A	119.5
N6—C8—C7	117.3 (2)	C17—C18—C13	119.0 (2)
C12—C8—C7	119.1 (2)	C17—C18—C20	115.9 (2)
N6—C9—C10	124.1 (3)	C13—C18—C20	125.0 (2)
N6—C9—H9	117.9	O1—C19—O2	123.0 (2)
C10—C9—H9	117.9	O1—C19—C13	123.0 (2)
C11—C10—C9	118.7 (3)	O2—C19—C13	114.0 (2)
C11—C10—H10	120.6	O4—C20—O3	124.1 (2)
C9—C10—H10	120.6	O4—C20—C18	123.9 (2)
C10—C11—C12	119.2 (3)	O3—C20—C18	111.8 (2)
N2—Cu1—N1—C2	−178.4 (2)	N6—C9—C10—C11	−0.3 (5)
N2i—Cu1—N1—C2	1.6 (2)	C9—C10—C11—C12	0.7 (4)
O1—Cu1—N1—C2	−86.26 (19)	C10—C11—C12—C8	0.4 (4)
N2—Cu1—N1—C1	2.92 (15)	N6—C8—C12—C11	−2.0 (4)
N2i—Cu1—N1—C1	−177.08 (15)	C7—C8—C12—C11	179.5 (2)
O1—Cu1—N1—C1	95.02 (15)	C26—C21—C22—C23	0.4 (3)
N1i—Cu1—N2—C6	177.47 (15)	C27—C21—C22—C23	−177.5 (2)
N1—Cu1—N2—C6	−2.53 (15)	C26—C21—C22—C28	179.2 (2)
O1—Cu1—N2—C6	−90.42 (15)	C27—C21—C22—C28	1.2 (4)
N1i—Cu1—N2—N3	−2.8 (2)	C21—C22—C23—C24	−1.1 (4)
N1—Cu1—N2—N3	177.2 (2)	C28—C22—C23—C24	179.9 (2)
O1—Cu1—N2—N3	89.3 (2)	C22—C23—C24—C25	1.0 (4)
C6—N2—N3—C7	−0.3 (2)	C23—C24—C25—C26	−0.1 (4)
Cu1—N2—N3—C7	179.97 (17)	C24—C25—C26—C21	−0.6 (4)
C2—N1—C1—C5	−0.9 (3)	C22—C21—C26—C25	0.4 (4)
Cu1—N1—C1—C5	177.90 (17)	C27—C21—C26—C25	178.6 (2)
C2—N1—C1—C6	178.53 (19)	C26—C21—C27—O5	−14.8 (3)
Cu1—N1—C1—C6	−2.6 (2)	C22—C21—C27—O5	163.2 (2)
C1—N1—C2—C3	0.9 (3)	C26—C21—C27—O6	164.4 (2)
Cu1—N1—C2—C3	−177.74 (18)	C22—C21—C27—O6	−17.6 (3)
N1—C2—C3—C4	−0.3 (4)	C23—C22—C28—O8	11.6 (3)
C2—C3—C4—C5	−0.4 (4)	C21—C22—C28—O8	−167.2 (2)
N1—C1—C5—C4	0.3 (4)	C23—C22—C28—O7	−166.9 (2)
C6—C1—C5—C4	−179.1 (2)	C21—C22—C28—O7	14.3 (4)
C3—C4—C5—C1	0.4 (4)	N2—Cu1—O1—C19	−148.0 (2)
N3—N2—C6—N4	1.2 (2)	N2i—Cu1—O1—C19	32.0 (2)
Cu1—N2—C6—N4	−179.01 (13)	N1i—Cu1—O1—C19	−48.7 (2)
N3—N2—C6—C1	−177.86 (18)	N1—Cu1—O1—C19	131.3 (2)
Cu1—N2—C6—C1	1.9 (2)	C18—C13—C14—C15	−0.9 (3)
C7—N4—C6—N2	−1.6 (2)	C19—C13—C14—C15	176.9 (2)
N5—N4—C6—N2	177.72 (18)	C13—C14—C15—C16	−1.5 (4)
C7—N4—C6—C1	177.3 (2)	C14—C15—C16—C17	2.0 (4)
N5—N4—C6—C1	−3.4 (4)	C15—C16—C17—C18	0.1 (4)
N1—C1—C6—N2	0.5 (3)	C16—C17—C18—C13	−2.5 (4)
C5—C1—C6—N2	179.9 (2)	C16—C17—C18—C20	172.8 (2)
N1—C1—C6—N4	−178.3 (2)	C14—C13—C18—C17	2.9 (3)
C5—C1—C6—N4	1.1 (4)	C19—C13—C18—C17	−174.8 (2)
N2—N3—C7—N4	−0.7 (2)	C14—C13—C18—C20	−172.0 (2)
N2—N3—C7—C8	177.3 (2)	C19—C13—C18—C20	10.3 (4)
C6—N4—C7—N3	1.4 (2)	Cu1—O1—C19—O2	−114.9 (2)
N5—N4—C7—N3	−177.8 (2)	Cu1—O1—C19—C13	68.1 (3)
C6—N4—C7—C8	−176.6 (2)	C14—C13—C19—O1	26.3 (3)
N5—N4—C7—C8	4.2 (4)	C18—C13—C19—O1	−155.9 (2)
C9—N6—C8—C12	2.3 (4)	C14—C13—C19—O2	−150.9 (2)
C9—N6—C8—C7	−179.2 (2)	C18—C13—C19—O2	26.9 (3)
N3—C7—C8—N6	179.9 (2)	C17—C18—C20—O4	62.5 (3)
N4—C7—C8—N6	−2.4 (3)	C13—C18—C20—O4	−122.5 (3)
N3—C7—C8—C12	−1.6 (3)	C17—C18—C20—O3	−112.5 (2)
N4—C7—C8—C12	176.1 (2)	C13—C18—C20—O3	62.5 (3)
C8—N6—C9—C10	−1.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5A···O6	0.90	2.23	2.957 (3)	137
N5—H5B···N6	0.90	2.23	2.871 (3)	128
O2—H2···O8ii	0.82	1.83	2.619 (2)	161
O3—H3···O5i	0.82	1.77	2.579 (2)	171
O7—H7···O6	0.82	1.60	2.394 (2)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5A⋯O6	0.90	2.23	2.957 (3)	137
N5—H5B⋯N6	0.90	2.23	2.871 (3)	128
O2—H2⋯O8i	0.82	1.83	2.619 (2)	161
O3—H3⋯O5ii	0.82	1.77	2.579 (2)	171
O7—H7⋯O6	0.82	1.60	2.394 (2)	163

Symmetry codes: (i) ; (ii) .