Bis(μ-4-formyl-benzoato-κ(2) O:O')bis-[(4-formyl-benzoato-κ(2) O,O')bis-(iso-nicotin-amide-κN (1))copper(II)].

The asymmetric unit of the centrosymmetric dinuclear title compound, [Cu2(C8H5O3)4(C6H6N2O)4], contains one half of the complex mol-ecule. The Cu(II) atoms are bridged by the carboxyl-ate groups of two 4-formyl-benzoate (FOB) anions. Besides the two bridging FOB anions, one additional chelating FOB anion and two isonicotinamide (INA) ligands complete the distorted CuN2O4 octa-hedral coordination of each Cu(2+) cation. Within the asymmetric unit, the benzene and pyridine rings are oriented at dihedral angles of 25.1 (3) and 12.6 (3)°, respectively. In the crystal, N-H⋯O and C-H⋯O hydrogen bonds link the mol-ecules into a three-dimensional network. π-π contacts between the pyridine rings [shortest centroid-centroid distance = 3.821 (3) Å] may further stabilize the crystal structure. One of the formyl groups of the two FOB anions is disordered over two sets of sites with an occupancy ratio of 0.65:0.35.

Related literature

For general background, see: Bigoli et al. (1972 ▶); Krishnamachari (1974 ▶). For related structures, see: Hökelek (1996 ▶, 2009a ▶,b ▶,c ▶)); Greenaway et al. (1984 ▶); Necefoğlu et al. (2011 ▶).

Experimental

Crystal data

[Cu2(C8H5O3)4(C6H6N2O)4]

M = 1212.09

Triclinic,

a = 8.6462 (2) Å

b = 11.6709 (3) Å

c = 13.4339 (4) Å

α = 87.876 (3)°

β = 83.483 (3)°

γ = 74.566 (2)°

V = 1298.24 (6) Å3

Z = 1

Mo Kα radiation

μ = 0.90 mm−1

T = 100 K

0.17 × 0.07 × 0.06 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.927, T max = 0.947

19200 measured reflections

6198 independent reflections

4412 reflections with I > 2σ(I)

R int = 0.189

Refinement

R[F 2 > 2σ(F 2)] = 0.078

wR(F 2) = 0.204

S = 1.11

6198 reflections

389 parameters

119 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.05 e Å−3

Δρmin = −1.51 e Å−3

Data collection: APEX2 (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: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813010908/wm2735sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813010908/wm2735Isup2.hkl

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

[Cu2(C8H5O3)4(C6H6N2O)4]	Z = 1
Mr = 1212.09	F(000) = 622
Triclinic, P1	Dx = 1.550 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.6462 (2) Å	Cell parameters from 6407 reflections
b = 11.6709 (3) Å	θ = 2.4–27.8°
c = 13.4339 (4) Å	µ = 0.90 mm−1
α = 87.876 (3)°	T = 100 K
β = 83.483 (3)°	Rod, blue
γ = 74.566 (2)°	0.17 × 0.07 × 0.06 mm
V = 1298.24 (6) Å3

Bruker Kappa APEXII CCD area-detector diffractometer	6198 independent reflections
Radiation source: fine-focus sealed tube	4412 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.189
φ and ω scans	θmax = 28.2°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −11→11
Tmin = 0.927, Tmax = 0.947	k = −15→15
19200 measured reflections	l = −16→17

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)] = 0.078	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.204	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ2(Fo2) + (0.076P)2 + 1.153P] where P = (Fo2 + 2Fc2)/3
6198 reflections	(Δ/σ)max < 0.001
389 parameters	Δρmax = 1.05 e Å−3
119 restraints	Δρmin = −1.51 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	Occ. (<1)
Cu1	0.62806 (7)	0.56954 (5)	0.88371 (4)	0.0185 (2)
O1	0.6218 (4)	0.7313 (3)	0.8280 (2)	0.0219 (8)
O2	0.8235 (4)	0.6237 (3)	0.7243 (3)	0.0242 (8)
O3	0.7284 (4)	0.3990 (3)	0.8858 (2)	0.0236 (8)
O4	0.6139 (4)	0.3497 (3)	1.0325 (3)	0.0234 (8)
O5A	0.5585 (8)	1.2043 (6)	0.4824 (4)	0.0358 (16)	0.65
O5B	0.7922 (16)	1.1019 (11)	0.3972 (9)	0.036 (3)	0.35
O6	0.9826 (6)	−0.2505 (4)	0.9067 (4)	0.0539 (13)
O7	0.1544 (5)	0.6109 (4)	0.4944 (3)	0.0413 (11)
O8	0.7785 (6)	0.7769 (5)	1.3297 (4)	0.075 (2)
N1	0.5025 (5)	0.5434 (4)	0.7713 (3)	0.0192 (8)
N2	0.7236 (5)	0.6046 (4)	1.0053 (3)	0.0205 (9)
N3	0.2635 (6)	0.4147 (4)	0.4793 (3)	0.0273 (10)
H3A	0.2147	0.4101	0.4278	0.033*
H3B	0.3264	0.3518	0.5024	0.033*
N4	0.9885 (5)	0.6171 (4)	1.3195 (3)	0.0250 (9)
H4A	1.0185	0.6325	1.3753	0.030*
H4B	1.0426	0.5553	1.2859	0.030*
C1	0.7234 (6)	0.7203 (4)	0.7504 (4)	0.0206 (10)
C2	0.7188 (6)	0.8266 (4)	0.6842 (4)	0.0222 (10)
C3	0.8351 (7)	0.8206 (5)	0.6028 (4)	0.0259 (11)
H3	0.9212	0.7530	0.5934	0.031*
C4	0.8234 (7)	0.9140 (5)	0.5363 (4)	0.0299 (12)
H4	0.9015	0.9094	0.4819	0.036*
C5	0.6953 (8)	1.0154 (5)	0.5500 (4)	0.0325 (13)
C6	0.5786 (7)	1.0235 (5)	0.6324 (4)	0.0339 (13)
H6	0.4930	1.0913	0.6421	0.041*
C7	0.5923 (7)	0.9294 (5)	0.6992 (4)	0.0286 (12)
H7	0.5163	0.9346	0.7548	0.034*
C8	0.6975 (5)	0.3243 (4)	0.9504 (3)	0.0172 (9)
C9	0.7701 (6)	0.1950 (4)	0.9257 (4)	0.0217 (10)
C10	0.7451 (7)	0.1082 (5)	0.9932 (4)	0.0269 (11)
H10	0.6821	0.1294	1.0539	0.032*
C11	0.8139 (7)	−0.0111 (5)	0.9706 (5)	0.0319 (12)
H11	0.7989	−0.0695	1.0168	0.038*
C12	0.9055 (7)	−0.0432 (5)	0.8787 (5)	0.0330 (13)
C13	0.9269 (7)	0.0436 (5)	0.8116 (4)	0.0322 (13)
H13	0.9874	0.0222	0.7502	0.039*
C14	0.8600 (7)	0.1626 (5)	0.8333 (4)	0.0283 (12)
H14	0.8749	0.2207	0.7866	0.034*
C15	0.3770 (6)	0.6306 (5)	0.7469 (4)	0.0233 (10)
H15	0.3460	0.6994	0.7850	0.028*
C16	0.2918 (6)	0.6235 (4)	0.6686 (4)	0.0233 (10)
H16	0.2064	0.6869	0.6537	0.028*
C17	0.3337 (6)	0.5212 (4)	0.6115 (3)	0.0211 (10)
C18	0.4627 (7)	0.4294 (5)	0.6364 (4)	0.0259 (11)
H18	0.4936	0.3591	0.6002	0.031*
C19	0.5449 (6)	0.4434 (4)	0.7153 (4)	0.0223 (10)
H19	0.6324	0.3820	0.7308	0.027*
C20	0.6678 (6)	0.7138 (4)	1.0458 (4)	0.0202 (10)
H20	0.5980	0.7726	1.0117	0.024*
C21	0.7102 (6)	0.7416 (5)	1.1354 (4)	0.0237 (11)
H21	0.6680	0.8175	1.1618	0.028*
C22	0.8170 (6)	0.6553 (5)	1.1866 (4)	0.0215 (10)
C23	0.8753 (6)	0.5437 (4)	1.1446 (4)	0.0206 (10)
H23	0.9476	0.4840	1.1763	0.025*
C24	0.8253 (6)	0.5224 (4)	1.0555 (4)	0.0204 (10)
H24	0.8643	0.4466	1.0285	0.024*
C25	0.6803 (9)	1.1107 (6)	0.4732 (4)	0.0406 (15)
H25A	0.748 (11)	1.094 (8)	0.410 (4)	0.035*	0.65
H25B	0.622 (17)	1.188 (4)	0.500 (10)	0.035*	0.35
C26	0.9852 (8)	−0.1697 (6)	0.8536 (5)	0.0397 (15)
H26	1.042 (5)	−0.189 (4)	0.793 (2)	0.016 (14)*
C27	0.2415 (6)	0.5188 (5)	0.5231 (4)	0.0241 (11)
C28	0.8602 (7)	0.6880 (5)	1.2856 (4)	0.0268 (11)

	U11	U22	U33	U12	U13	U23
Cu1	0.0193 (4)	0.0219 (3)	0.0121 (3)	−0.0046 (2)	0.0078 (2)	−0.0045 (2)
O1	0.029 (2)	0.0195 (16)	0.0144 (17)	−0.0054 (15)	0.0067 (14)	−0.0028 (13)
O2	0.025 (2)	0.0264 (17)	0.0173 (18)	−0.0027 (15)	0.0065 (15)	−0.0011 (14)
O3	0.033 (2)	0.0251 (17)	0.0121 (17)	−0.0100 (16)	0.0039 (15)	−0.0005 (14)
O4	0.0201 (19)	0.0293 (18)	0.0181 (18)	−0.0055 (15)	0.0093 (14)	−0.0068 (14)
O5A	0.048 (4)	0.034 (3)	0.023 (3)	−0.011 (3)	0.004 (3)	0.000 (3)
O5B	0.050 (9)	0.027 (5)	0.027 (6)	−0.009 (5)	0.014 (5)	0.008 (5)
O6	0.046 (3)	0.037 (2)	0.079 (4)	−0.008 (2)	−0.008 (3)	−0.009 (2)
O7	0.046 (3)	0.038 (2)	0.033 (2)	0.006 (2)	−0.015 (2)	−0.0141 (19)
O8	0.062 (3)	0.083 (4)	0.053 (3)	0.043 (3)	−0.034 (3)	−0.053 (3)
N1	0.015 (2)	0.026 (2)	0.015 (2)	−0.0069 (16)	0.0081 (16)	−0.0036 (16)
N2	0.023 (2)	0.024 (2)	0.014 (2)	−0.0075 (17)	0.0065 (16)	−0.0044 (15)
N3	0.038 (3)	0.029 (2)	0.015 (2)	−0.008 (2)	0.0000 (19)	−0.0048 (17)
N4	0.025 (2)	0.031 (2)	0.015 (2)	−0.0040 (19)	0.0050 (18)	−0.0084 (18)
C1	0.023 (3)	0.025 (2)	0.013 (2)	−0.006 (2)	0.0030 (19)	−0.0040 (18)
C2	0.025 (3)	0.024 (2)	0.016 (2)	−0.007 (2)	0.006 (2)	−0.0051 (19)
C3	0.028 (3)	0.029 (2)	0.019 (3)	−0.007 (2)	0.006 (2)	−0.003 (2)
C4	0.039 (3)	0.033 (3)	0.018 (3)	−0.014 (2)	0.010 (2)	−0.003 (2)
C5	0.050 (4)	0.029 (3)	0.019 (3)	−0.014 (2)	0.006 (2)	0.001 (2)
C6	0.039 (4)	0.027 (3)	0.031 (3)	−0.003 (2)	0.002 (2)	0.000 (2)
C7	0.032 (3)	0.029 (2)	0.021 (3)	−0.005 (2)	0.011 (2)	−0.003 (2)
C8	0.005 (2)	0.024 (2)	0.019 (2)	−0.0007 (18)	0.0043 (18)	−0.0035 (18)
C9	0.015 (3)	0.024 (2)	0.023 (3)	−0.0026 (19)	0.006 (2)	−0.0065 (19)
C10	0.022 (3)	0.029 (2)	0.027 (3)	−0.006 (2)	0.006 (2)	−0.003 (2)
C11	0.030 (3)	0.026 (2)	0.041 (3)	−0.010 (2)	−0.006 (2)	0.004 (2)
C12	0.027 (3)	0.030 (3)	0.042 (3)	−0.005 (2)	−0.004 (3)	−0.011 (2)
C13	0.026 (3)	0.034 (3)	0.031 (3)	0.000 (2)	0.008 (2)	−0.016 (2)
C14	0.027 (3)	0.028 (3)	0.026 (3)	−0.005 (2)	0.008 (2)	−0.006 (2)
C15	0.020 (3)	0.027 (2)	0.018 (3)	−0.002 (2)	0.009 (2)	−0.007 (2)
C16	0.021 (3)	0.025 (2)	0.020 (3)	−0.002 (2)	0.006 (2)	−0.005 (2)
C17	0.022 (3)	0.029 (2)	0.011 (2)	−0.008 (2)	0.0121 (19)	−0.0041 (19)
C18	0.030 (3)	0.029 (2)	0.016 (2)	−0.007 (2)	0.010 (2)	−0.010 (2)
C19	0.022 (3)	0.024 (2)	0.016 (2)	−0.001 (2)	0.010 (2)	−0.0061 (19)
C20	0.017 (3)	0.022 (2)	0.016 (2)	−0.0008 (19)	0.0081 (19)	−0.0033 (18)
C21	0.024 (3)	0.025 (2)	0.018 (2)	−0.002 (2)	0.007 (2)	−0.0076 (19)
C22	0.019 (3)	0.030 (2)	0.013 (2)	−0.006 (2)	0.0054 (19)	−0.0025 (19)
C23	0.021 (3)	0.023 (2)	0.014 (2)	−0.0026 (19)	0.0085 (19)	−0.0035 (18)
C24	0.016 (3)	0.026 (2)	0.015 (2)	−0.0045 (19)	0.0124 (19)	−0.0042 (19)
C25	0.063 (5)	0.034 (3)	0.024 (3)	−0.013 (3)	0.002 (3)	0.001 (2)
C26	0.035 (4)	0.034 (3)	0.052 (4)	−0.009 (3)	−0.016 (3)	−0.003 (3)
C27	0.025 (3)	0.034 (3)	0.012 (2)	−0.010 (2)	0.011 (2)	−0.007 (2)
C28	0.024 (3)	0.035 (3)	0.018 (3)	−0.001 (2)	0.005 (2)	−0.010 (2)

Cu1—O1	1.994 (3)	C7—C6	1.382 (8)
Cu1—O2	2.736 (4)	C7—H7	0.9300
Cu1—O3	1.949 (4)	C8—C9	1.506 (7)
Cu1—O4i	2.242 (3)	C9—C10	1.378 (7)
Cu1—N1	2.033 (4)	C9—C14	1.395 (7)
Cu1—N2	2.013 (4)	C10—H10	0.9300
O1—C1	1.271 (6)	C11—C10	1.390 (7)
O2—C1	1.259 (6)	C11—C12	1.395 (8)
O3—C8	1.264 (6)	C11—H11	0.9300
O4—C8	1.248 (6)	C12—C13	1.366 (9)
O4—Cu1i	2.242 (3)	C13—H13	0.9300
O5A—C25	1.299 (9)	C14—C13	1.384 (7)
O5A—H25B	0.61 (19)	C14—H14	0.9300
O5B—C25	1.311 (11)	C15—C16	1.367 (7)
O5B—H25A	0.43 (10)	C15—H15	0.9300
O6—C26	1.165 (8)	C16—H16	0.9300
O7—C27	1.215 (7)	C17—C16	1.385 (6)
N1—C15	1.338 (7)	C17—C27	1.508 (7)
N1—C19	1.356 (6)	C18—C17	1.388 (8)
N2—C20	1.349 (6)	C18—H18	0.9300
N2—C24	1.336 (7)	C19—C18	1.379 (7)
N3—C27	1.328 (6)	C19—H19	0.9300
N3—H3A	0.8600	C20—C21	1.371 (7)
N3—H3B	0.8600	C20—H20	0.9300
N4—C28	1.312 (7)	C21—C22	1.392 (7)
N4—H4A	0.8600	C21—H21	0.9300
N4—H4B	0.8600	C22—C28	1.511 (7)
C1—C2	1.494 (7)	C23—C22	1.381 (7)
C3—C4	1.374 (7)	C23—C24	1.370 (7)
C3—C2	1.389 (7)	C23—H23	0.9300
C3—H3	0.9300	C24—H24	0.9300
C4—H4	0.9300	C25—H25A	0.97 (2)
C5—C4	1.391 (8)	C25—H25B	0.97 (2)
C5—C25	1.479 (8)	C26—C12	1.487 (8)
C6—C5	1.398 (8)	C26—H26	0.90 (2)
C6—H6	0.9300	C28—O8	1.220 (6)
C7—C2	1.395 (7)
O1—Cu1—O4i	87.34 (13)	C12—C11—H11	120.0
O1—Cu1—N1	88.89 (15)	C11—C12—C26	121.4 (6)
O1—Cu1—N2	90.93 (15)	C13—C12—C11	119.4 (5)
O3—Cu1—O1	150.35 (14)	C13—C12—C26	119.2 (5)
O3—Cu1—O4i	121.93 (13)	C12—C13—C14	121.2 (5)
O3—Cu1—N1	88.74 (16)	C12—C13—H13	119.4
O3—Cu1—N2	95.15 (16)	C14—C13—H13	119.4
N1—Cu1—O4i	85.80 (14)	C9—C14—H14	120.3
N2—Cu1—O4i	86.58 (15)	C13—C14—C9	119.5 (5)
N2—Cu1—N1	172.37 (16)	C13—C14—H14	120.3
C1—O1—Cu1	108.3 (3)	N1—C15—C16	123.3 (4)
C8—O3—Cu1	127.1 (3)	N1—C15—H15	118.4
C8—O4—Cu1i	148.5 (3)	C16—C15—H15	118.4
C15—N1—Cu1	119.3 (3)	C15—C16—C17	119.6 (5)
C15—N1—C19	117.5 (4)	C15—C16—H16	120.2
C19—N1—Cu1	123.1 (4)	C17—C16—H16	120.2
C20—N2—Cu1	118.3 (4)	C16—C17—C18	117.9 (5)
C24—N2—Cu1	123.9 (3)	C16—C17—C27	118.0 (5)
C24—N2—C20	117.3 (4)	C18—C17—C27	124.1 (4)
C27—N3—H3A	120.0	C17—C18—H18	120.3
C27—N3—H3B	120.0	C19—C18—C17	119.4 (4)
H3A—N3—H3B	120.0	C19—C18—H18	120.3
C28—N4—H4A	120.0	N1—C19—C18	122.3 (5)
C28—N4—H4B	120.0	N1—C19—H19	118.8
H4A—N4—H4B	120.0	C18—C19—H19	118.8
O1—C1—C2	118.2 (4)	N2—C20—C21	122.5 (5)
O2—C1—O1	123.6 (5)	N2—C20—H20	118.7
O2—C1—C2	118.2 (4)	C21—C20—H20	118.7
C3—C2—C7	119.5 (5)	C20—C21—C22	119.4 (5)
C3—C2—C1	119.9 (5)	C20—C21—H21	120.3
C7—C2—C1	120.5 (4)	C22—C21—H21	120.3
C2—C3—H3	119.9	C21—C22—C28	118.3 (5)
C4—C3—C2	120.2 (5)	C23—C22—C21	118.0 (5)
C4—C3—H3	119.9	C23—C22—C28	123.7 (5)
C4—C5—C6	120.2 (5)	C22—C23—H23	120.5
C4—C5—C25	118.8 (5)	C24—C23—C22	119.0 (5)
C6—C5—C25	121.0 (6)	C24—C23—H23	120.5
C3—C4—C5	120.3 (5)	N2—C24—C23	123.6 (5)
C3—C4—H4	119.9	N2—C24—H24	118.2
C5—C4—H4	119.9	C23—C24—H24	118.2
C5—C6—H6	120.5	O5A—C25—O5B	120.1 (8)
C7—C6—C5	119.0 (5)	O5A—C25—C5	119.9 (6)
C7—C6—H6	120.5	O5B—C25—C5	119.9 (8)
C2—C7—H7	119.6	O5A—C25—H25A	120 (5)
C6—C7—C2	120.8 (5)	C5—C25—H25A	118 (5)
C6—C7—H7	119.6	O5B—C25—H25B	120 (5)
O3—C8—C9	116.7 (4)	C5—C25—H25B	113 (7)
O4—C8—O3	125.1 (5)	H25A—C25—H25B	127 (8)
O4—C8—C9	118.2 (4)	O6—C26—C12	125.3 (7)
C10—C9—C8	120.2 (4)	O6—C26—H26	114 (3)
C10—C9—C14	119.8 (5)	C12—C26—H26	120 (3)
C14—C9—C8	120.0 (5)	O7—C27—N3	123.4 (5)
C9—C10—C11	120.0 (5)	O7—C27—C17	119.3 (5)
C9—C10—H10	120.0	N3—C27—C17	117.3 (5)
C11—C10—H10	120.0	O8—C28—N4	123.1 (5)
C10—C11—C12	120.1 (5)	O8—C28—C22	120.3 (5)
C10—C11—H11	120.0	N4—C28—C22	116.6 (4)
O3—Cu1—O1—C1	9.8 (5)	C6—C5—C25—O5A	0.9 (9)
O4i—Cu1—O1—C1	−161.5 (3)	C6—C5—C25—O5B	179.1 (9)
N1—Cu1—O1—C1	−75.7 (3)	C7—C6—C5—C4	−0.4 (9)
N2—Cu1—O1—C1	111.9 (3)	C7—C6—C5—C25	176.2 (6)
O1—Cu1—O3—C8	169.2 (4)	C6—C7—C2—C1	−173.4 (5)
O4i—Cu1—O3—C8	−21.0 (4)	C6—C7—C2—C3	2.1 (8)
N1—Cu1—O3—C8	−105.2 (4)	C2—C7—C6—C5	−1.1 (9)
N2—Cu1—O3—C8	68.2 (4)	O3—C8—C9—C10	178.6 (5)
O1—Cu1—N1—C19	132.7 (4)	O3—C8—C9—C14	−2.8 (7)
O3—Cu1—N1—C15	165.9 (4)	O4—C8—C9—C10	−0.7 (7)
O3—Cu1—N1—C19	−17.7 (4)	O4—C8—C9—C14	177.9 (5)
O4i—Cu1—N1—C15	43.8 (4)	C8—C9—C10—C11	−179.2 (5)
O4i—Cu1—N1—C19	−139.9 (4)	C14—C9—C10—C11	2.2 (8)
O1—Cu1—N2—C20	39.5 (3)	C8—C9—C14—C13	179.6 (5)
O1—Cu1—N2—C24	−148.6 (4)	C10—C9—C14—C13	−1.7 (8)
O3—Cu1—N2—C20	−169.5 (3)	C12—C11—C10—C9	−1.4 (8)
O3—Cu1—N2—C24	2.4 (4)	C10—C11—C12—C13	0.1 (9)
O4i—Cu1—N2—C20	−47.7 (3)	C10—C11—C12—C26	178.0 (5)
O4i—Cu1—N2—C24	124.1 (4)	C11—C12—C13—C14	0.3 (9)
Cu1—O1—C1—O2	−8.7 (6)	C26—C12—C13—C14	−177.6 (5)
Cu1—O1—C1—C2	168.4 (3)	C9—C14—C13—C12	0.5 (9)
Cu1—O3—C8—O4	−11.3 (7)	N1—C15—C16—C17	1.0 (8)
Cu1—O3—C8—C9	169.5 (3)	C18—C17—C16—C15	−0.4 (7)
Cu1i—O4—C8—O3	65.4 (8)	C27—C17—C16—C15	−177.4 (4)
Cu1i—O4—C8—C9	−115.4 (6)	C16—C17—C27—O7	12.4 (7)
Cu1—N1—C15—C16	176.0 (4)	C16—C17—C27—N3	−169.0 (4)
C19—N1—C15—C16	−0.6 (7)	C18—C17—C27—O7	−164.4 (5)
Cu1—N1—C19—C18	−177.0 (4)	C18—C17—C27—N3	14.2 (7)
C15—N1—C19—C18	−0.5 (7)	C19—C18—C17—C16	−0.6 (7)
Cu1—N2—C20—C21	171.6 (4)	C19—C18—C17—C27	176.2 (4)
C24—N2—C20—C21	−0.8 (7)	N1—C19—C18—C17	1.1 (7)
Cu1—N2—C24—C23	−172.2 (3)	N2—C20—C21—C22	1.2 (7)
C20—N2—C24—C23	−0.2 (7)	C20—C21—C22—C23	−0.5 (7)
O1—C1—C2—C3	175.4 (5)	C20—C21—C22—C28	−179.4 (4)
O1—C1—C2—C7	−9.1 (7)	C21—C22—C28—O8	15.8 (8)
O2—C1—C2—C3	−7.3 (7)	C21—C22—C28—N4	−163.5 (5)
O2—C1—C2—C7	168.2 (5)	C23—C22—C28—O8	−163.0 (6)
C4—C3—C2—C1	174.0 (5)	C23—C22—C28—N4	17.6 (7)
C4—C3—C2—C7	−1.6 (8)	C24—C23—C22—C21	−0.5 (7)
C2—C3—C4—C5	0.1 (8)	C24—C23—C22—C28	178.3 (4)
C6—C5—C4—C3	0.9 (9)	C22—C23—C24—N2	0.9 (7)
C25—C5—C4—C3	−175.8 (5)	O6—C26—C12—C11	−2.0 (10)
C4—C5—C25—O5A	177.5 (6)	O6—C26—C12—C13	175.9 (6)
C4—C5—C25—O5B	−4.2 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O2ii	0.86	2.17	2.997 (6)	160
N3—H3B···O5Aiii	0.86	2.27	3.044 (9)	149
N4—H4A···O7iv	0.86	2.06	2.878 (6)	158
N4—H4B···O2v	0.86	2.10	2.890 (6)	152
C3—H3···O7vi	0.93	2.52	3.391 (7)	155
C6—H6···O8vii	0.93	2.44	3.336 (9)	162
C18—H18···O5Aiii	0.93	2.35	3.274 (9)	169
C23—H23···O2v	0.93	2.54	3.432 (7)	162
C24—H24···O6viii	0.93	2.50	3.217 (7)	134

Table 1

Selected bond lengths (Å)

Cu1—O1	1.994 (3)
Cu1—O2	2.736 (4)
Cu1—O3	1.949 (4)
Cu1—O4i	2.242 (3)
Cu1—N1	2.033 (4)
Cu1—N2	2.013 (4)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O2ii	0.86	2.17	2.997 (6)	160
N3—H3B⋯O5A iii	0.86	2.27	3.044 (9)	149
N4—H4A⋯O7iv	0.86	2.06	2.878 (6)	158
N4—H4B⋯O2v	0.86	2.10	2.890 (6)	152
C3—H3⋯O7vi	0.93	2.52	3.391 (7)	155
C6—H6⋯O8vii	0.93	2.44	3.336 (9)	162
C18—H18⋯O5A iii	0.93	2.35	3.274 (9)	169
C23—H23⋯O2v	0.93	2.54	3.432 (7)	162
C24—H24⋯O6viii	0.93	2.50	3.217 (7)	134

Symmetry codes: (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) ; (viii) .