Bis(3-chloro-benzoato-κ(2) O,O')bis-(nicotinamide-κN)copper(II).

The mol-ecule of the title Cu(II) complex, [Cu(C7H4ClO2)2(C6H6N2O)2], contains two 3-chloro-benzoate (CB) and two nicotinamide (NA) ligands; the CB act as bidentate ligands, while the NA are monodentate ligands. The resulting CuN2O4 coordination polyhedron is a considerably distorted octahedron. The dihedral angles between the carboxyl-ate groups and the adjacent benzene rings are 17.92 (12) and 24.69 (16)°, while the two benzene rings and the two pyridine rings are oriented at dihedral angles of 52.20 (8) and 1.56 (6)°. In the crystal, N-H⋯N and C-H⋯O hydrogen bonds link the mol-ecules into a three-dimensional network. The π-π contact between the benzene rings [centroid-centroid distance = 3.982 (2) Å] may further stabilize the crystal structure.

Related literature

For niacin, see: Krishnamachari (1974 ▶). For the nicotinic acid derivative N,N-di­ethyl­nicotinamide, see: Bigoli et al. (1972 ▶). For related structures, see: Greenaway et al. (1984 ▶); Hökelek & Necefoğlu (1996 ▶); Hökelek et al. (1996 ▶); Hökelek, Dal et al. (2009 ▶); Hökelek, Yılmaz et al. (2009 ▶); Necefoğlu et al. (2011 ▶); Sertçelik et al. (2013 ▶).

Experimental

Crystal data

[Cu(C7H4ClO2)2(C6H6N2O)2]

M = 618.91

Triclinic,

a = 9.6614 (2) Å

b = 12.5429 (3) Å

c = 12.8728 (3) Å

α = 61.598 (2)°

β = 87.386 (3)°

γ = 77.115 (3)°

V = 1334.30 (6) Å3

Z = 2

Mo Kα radiation

μ = 1.07 mm−1

T = 296 K

0.35 × 0.20 × 0.15 mm

Data collection

Bruker SMART BREEZE CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2012 ▶) T min = 0.774, T max = 0.852

19053 measured reflections

5434 independent reflections

4970 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.083

S = 1.06

5434 reflections

368 parameters

117 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.43 e Å−3

Δρmin = −0.43 e Å−3

Data collection: APEX2 (Bruker, 2012 ▶); cell refinement: SAINT (Bruker, 2012 ▶); 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 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813014694/rk2404sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813014694/rk2404Isup2.hkl

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

[Cu(C7H4ClO2)2(C6H6N2O)2]	Z = 2
Mr = 618.91	F(000) = 630
Triclinic, P1	Dx = 1.541 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.6614 (2) Å	Cell parameters from 9977 reflections
b = 12.5429 (3) Å	θ = 2.2–28.3°
c = 12.8728 (3) Å	µ = 1.07 mm−1
α = 61.598 (2)°	T = 296 K
β = 87.386 (3)°	Block, blue
γ = 77.115 (3)°	0.35 × 0.20 × 0.15 mm
V = 1334.30 (6) Å3

Bruker SMART BREEZE CCD diffractometer	5434 independent reflections
Radiation source: fine–focus sealed tube	4970 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
φ and ω scans	θmax = 26.4°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −12→12
Tmin = 0.774, Tmax = 0.852	k = −15→15
19053 measured reflections	l = −16→16

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0431P)2 + 0.6228P] where P = (Fo2 + 2Fc2)/3
5434 reflections	(Δ/σ)max = 0.001
368 parameters	Δρmax = 0.43 e Å−3
117 restraints	Δρmin = −0.43 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	0.27888 (2)	1.000999 (18)	0.199774 (17)	0.02922 (8)
Cl1	0.80542 (9)	0.43210 (7)	0.58781 (9)	0.0953 (3)
Cl2	−0.34732 (8)	1.57612 (7)	−0.04862 (10)	0.1008 (3)
O1	0.38881 (17)	0.84400 (13)	0.15270 (12)	0.0491 (4)
O2	0.39807 (13)	0.83886 (11)	0.32503 (11)	0.0345 (3)
O3	0.18430 (14)	1.14369 (12)	0.05257 (11)	0.0375 (3)
O4	0.0977 (2)	1.19856 (14)	0.18577 (12)	0.0570 (4)
O5	0.76794 (14)	1.14536 (16)	0.40191 (15)	0.0545 (4)
O6	−0.25440 (15)	0.82581 (19)	0.51564 (15)	0.0641 (5)
N1	0.43976 (16)	1.08071 (13)	0.18924 (12)	0.0318 (3)
N2	0.54419 (18)	1.16359 (17)	0.45497 (15)	0.0398 (4)
H2A	0.565 (2)	1.176 (2)	0.507 (2)	0.040 (6)*
H2B	0.458 (3)	1.172 (2)	0.440 (2)	0.050 (6)*
N3	0.10420 (15)	0.93169 (13)	0.24499 (12)	0.0315 (3)
N4	−0.04948 (19)	0.83277 (19)	0.58345 (16)	0.0435 (4)
H4A	0.034 (3)	0.841 (2)	0.574 (2)	0.048 (6)*
H4B	−0.079 (3)	0.818 (2)	0.648 (2)	0.058 (7)*
C1	0.4330 (2)	0.78886 (17)	0.25815 (16)	0.0354 (4)
C2	0.5297 (2)	0.66138 (17)	0.31005 (18)	0.0411 (4)
C3	0.6115 (2)	0.61181 (18)	0.4143 (2)	0.0448 (5)
H3	0.6067	0.6566	0.4553	0.054*
C4	0.7010 (2)	0.4944 (2)	0.4575 (2)	0.0551 (6)
C5	0.7073 (3)	0.4258 (2)	0.3993 (3)	0.0701 (7)
H5	0.7664	0.3465	0.4298	0.084*
C6	0.6252 (4)	0.4758 (2)	0.2957 (3)	0.0791 (9)
H6	0.6283	0.4298	0.2560	0.095*
C7	0.5381 (3)	0.5933 (2)	0.2499 (2)	0.0640 (7)
H7	0.4848	0.6272	0.1785	0.077*
C8	0.1053 (2)	1.21991 (17)	0.08210 (16)	0.0377 (4)
C9	0.0182 (2)	1.33707 (17)	−0.01605 (17)	0.0391 (4)
C10	−0.1053 (2)	1.39805 (18)	0.0098 (2)	0.0487 (5)
H10	−0.1309	1.3691	0.0875	0.058*
C11	−0.1900 (2)	1.5022 (2)	−0.0812 (2)	0.0582 (6)
C12	−0.1515 (3)	1.5492 (2)	−0.1967 (2)	0.0668 (7)
H12	−0.2098	1.6192	−0.2573	0.080*
C13	−0.0263 (3)	1.4911 (2)	−0.2205 (2)	0.0640 (6)
H13	0.0021	1.5236	−0.2975	0.077*
C14	0.0587 (3)	1.3845 (2)	−0.13122 (18)	0.0498 (5)
H14	0.1426	1.3448	−0.1486	0.060*
C15	0.47759 (18)	1.09464 (16)	0.28005 (14)	0.0307 (3)
H15	0.4211	1.0749	0.3442	0.037*
C16	0.59731 (17)	1.13714 (15)	0.28251 (15)	0.0297 (3)
C17	0.6804 (2)	1.16596 (19)	0.18655 (18)	0.0412 (4)
H17	0.7637	1.1914	0.1866	0.049*
C18	0.6388 (2)	1.1566 (2)	0.09122 (18)	0.0474 (5)
H18	0.6915	1.1789	0.0248	0.057*
C19	0.5179 (2)	1.11393 (19)	0.09505 (16)	0.0405 (4)
H19	0.4899	1.1080	0.0302	0.049*
C20	0.64242 (18)	1.14888 (16)	0.38547 (16)	0.0334 (4)
C21	0.05121 (18)	0.90891 (16)	0.34942 (15)	0.0308 (3)
H21	0.0993	0.9225	0.4014	0.037*
C22	−0.07235 (18)	0.86597 (16)	0.38352 (15)	0.0319 (4)
C23	−0.1438 (2)	0.8479 (2)	0.30439 (18)	0.0444 (5)
H23	−0.2282	0.8210	0.3234	0.053*
C24	−0.0884 (2)	0.8701 (2)	0.19695 (19)	0.0494 (5)
H24	−0.1344	0.8574	0.1432	0.059*
C25	0.0353 (2)	0.91112 (19)	0.17077 (17)	0.0408 (4)
H25	0.0728	0.9252	0.0987	0.049*
C26	−0.13259 (19)	0.84043 (18)	0.50037 (17)	0.0380 (4)

	U11	U22	U33	U12	U13	U23
Cu1	0.03384 (13)	0.03311 (12)	0.02251 (11)	−0.01037 (9)	0.00167 (8)	−0.01354 (9)
Cl1	0.0746 (5)	0.0701 (4)	0.1137 (7)	0.0100 (4)	−0.0438 (5)	−0.0290 (4)
Cl2	0.0536 (4)	0.0683 (4)	0.1427 (8)	0.0039 (3)	0.0142 (4)	−0.0287 (5)
O1	0.0689 (10)	0.0471 (8)	0.0279 (7)	−0.0023 (7)	0.0038 (6)	−0.0200 (6)
O2	0.0412 (7)	0.0358 (6)	0.0285 (6)	−0.0055 (5)	0.0001 (5)	−0.0180 (5)
O3	0.0451 (7)	0.0373 (6)	0.0279 (6)	−0.0085 (6)	−0.0017 (5)	−0.0138 (5)
O4	0.0919 (12)	0.0461 (8)	0.0290 (7)	−0.0090 (8)	0.0040 (7)	−0.0175 (6)
O5	0.0295 (7)	0.0882 (11)	0.0697 (10)	−0.0180 (7)	0.0031 (7)	−0.0548 (9)
O6	0.0336 (8)	0.1099 (14)	0.0543 (10)	−0.0324 (8)	0.0127 (7)	−0.0376 (10)
N1	0.0362 (7)	0.0352 (7)	0.0256 (7)	−0.0118 (6)	0.0024 (6)	−0.0144 (6)
N2	0.0334 (9)	0.0622 (11)	0.0368 (9)	−0.0152 (7)	0.0031 (7)	−0.0322 (8)
N3	0.0344 (7)	0.0346 (7)	0.0266 (7)	−0.0093 (6)	0.0006 (6)	−0.0148 (6)
N4	0.0315 (9)	0.0711 (12)	0.0331 (9)	−0.0195 (8)	0.0094 (7)	−0.0262 (8)
C1	0.0398 (9)	0.0360 (9)	0.0327 (9)	−0.0111 (7)	0.0080 (7)	−0.0177 (7)
C2	0.0451 (11)	0.0366 (9)	0.0419 (10)	−0.0110 (8)	0.0123 (8)	−0.0192 (8)
C3	0.0408 (10)	0.0402 (10)	0.0536 (12)	−0.0091 (8)	0.0040 (9)	−0.0226 (9)
C4	0.0400 (11)	0.0442 (11)	0.0685 (15)	−0.0062 (9)	0.0014 (10)	−0.0181 (11)
C5	0.0697 (16)	0.0405 (12)	0.088 (2)	0.0011 (11)	0.0127 (14)	−0.0276 (13)
C6	0.114 (2)	0.0505 (14)	0.0786 (19)	−0.0030 (15)	0.0115 (17)	−0.0426 (14)
C7	0.0931 (19)	0.0480 (12)	0.0525 (14)	−0.0053 (12)	0.0044 (13)	−0.0300 (11)
C8	0.0476 (10)	0.0350 (9)	0.0313 (9)	−0.0130 (8)	0.0014 (8)	−0.0148 (7)
C9	0.0482 (11)	0.0327 (9)	0.0353 (10)	−0.0133 (8)	0.0000 (8)	−0.0134 (8)
C10	0.0497 (12)	0.0373 (10)	0.0529 (12)	−0.0149 (9)	0.0078 (9)	−0.0148 (9)
C11	0.0430 (12)	0.0389 (11)	0.0801 (17)	−0.0089 (9)	−0.0009 (11)	−0.0183 (11)
C12	0.0701 (16)	0.0426 (12)	0.0636 (16)	−0.0101 (11)	−0.0198 (13)	−0.0054 (11)
C13	0.0832 (18)	0.0534 (13)	0.0370 (12)	−0.0156 (12)	−0.0041 (11)	−0.0065 (10)
C14	0.0611 (13)	0.0457 (11)	0.0361 (10)	−0.0123 (10)	0.0024 (9)	−0.0144 (9)
C15	0.0330 (8)	0.0365 (8)	0.0243 (8)	−0.0123 (7)	0.0053 (6)	−0.0143 (7)
C16	0.0282 (8)	0.0321 (8)	0.0296 (8)	−0.0081 (6)	0.0031 (6)	−0.0150 (7)
C17	0.0364 (10)	0.0513 (11)	0.0419 (10)	−0.0188 (8)	0.0117 (8)	−0.0239 (9)
C18	0.0488 (11)	0.0652 (13)	0.0333 (10)	−0.0234 (10)	0.0183 (8)	−0.0245 (10)
C19	0.0464 (11)	0.0525 (11)	0.0277 (9)	−0.0152 (9)	0.0073 (8)	−0.0219 (8)
C20	0.0296 (8)	0.0374 (9)	0.0374 (9)	−0.0096 (7)	0.0001 (7)	−0.0203 (8)
C21	0.0312 (8)	0.0375 (9)	0.0276 (8)	−0.0104 (7)	0.0000 (6)	−0.0174 (7)
C22	0.0286 (8)	0.0351 (8)	0.0315 (9)	−0.0074 (7)	−0.0009 (7)	−0.0151 (7)
C23	0.0392 (10)	0.0553 (12)	0.0450 (11)	−0.0207 (9)	−0.0010 (8)	−0.0244 (10)
C24	0.0547 (12)	0.0657 (13)	0.0436 (11)	−0.0237 (11)	−0.0028 (9)	−0.0339 (10)
C25	0.0492 (11)	0.0500 (11)	0.0302 (9)	−0.0150 (9)	0.0018 (8)	−0.0231 (8)
C26	0.0279 (9)	0.0484 (10)	0.0370 (10)	−0.0114 (8)	0.0050 (7)	−0.0188 (8)

Cu1—O1	2.3487 (14)	C6—H6	0.9300
Cu1—O2	2.0168 (12)	C7—C6	1.376 (4)
Cu1—O3	1.9574 (12)	C7—H7	0.9300
Cu1—O4	2.6280 (12)	C8—C9	1.498 (3)
Cu1—N1	1.9947 (14)	C9—C10	1.385 (3)
Cu1—N3	2.0065 (14)	C9—C14	1.384 (3)
Cu1—C1	2.5090 (18)	C10—C11	1.379 (3)
Cl1—C4	1.731 (3)	C10—H10	0.9300
Cl2—C11	1.740 (3)	C11—C12	1.382 (4)
O1—C1	1.237 (2)	C12—H12	0.9300
O2—C1	1.281 (2)	C13—C12	1.369 (4)
O3—C8	1.279 (2)	C13—H13	0.9300
O4—C8	1.232 (2)	C14—C13	1.385 (3)
O5—C20	1.228 (2)	C14—H14	0.9300
O6—C26	1.224 (2)	C15—H15	0.9300
N1—C15	1.339 (2)	C16—C15	1.385 (2)
N1—C19	1.338 (2)	C16—C17	1.384 (2)
N2—C20	1.318 (2)	C16—C20	1.495 (2)
N2—H2A	0.79 (2)	C17—C18	1.373 (3)
N2—H2B	0.84 (3)	C17—H17	0.9300
N3—C21	1.337 (2)	C18—H18	0.9300
N3—C25	1.338 (2)	C19—C18	1.379 (3)
N4—C26	1.321 (2)	C19—H19	0.9300
N4—H4A	0.83 (3)	C21—C22	1.386 (2)
N4—H4B	0.81 (3)	C21—H21	0.9300
C1—C2	1.500 (3)	C22—C23	1.385 (3)
C2—C3	1.377 (3)	C22—C26	1.500 (3)
C2—C7	1.388 (3)	C23—C24	1.382 (3)
C3—C4	1.387 (3)	C23—H23	0.9300
C3—H3	0.9300	C24—H24	0.9300
C4—C5	1.376 (4)	C25—C24	1.371 (3)
C5—C6	1.371 (4)	C25—H25	0.9300
C5—H5	0.9300
O1—Cu1—C1	29.28 (5)	O4—C8—O3	122.57 (17)
O2—Cu1—O1	59.76 (5)	O4—C8—C9	120.80 (18)
O2—Cu1—C1	30.48 (5)	C10—C9—C8	118.89 (18)
O3—Cu1—O1	106.81 (5)	C14—C9—C8	121.26 (19)
O3—Cu1—O2	166.26 (5)	C14—C9—C10	119.85 (19)
O3—Cu1—O4	55.08 (5)	C9—C10—H10	120.4
O3—Cu1—N1	91.50 (6)	C11—C10—C9	119.2 (2)
O3—Cu1—N3	93.10 (6)	C11—C10—H10	120.4
O3—Cu1—C1	136.00 (6)	C10—C11—Cl2	119.0 (2)
N1—Cu1—O1	100.98 (6)	C10—C11—C12	121.3 (2)
N1—Cu1—O2	88.65 (5)	C12—C11—Cl2	119.71 (19)
N1—Cu1—N3	164.90 (6)	C11—C12—H12	120.5
N1—Cu1—C1	95.33 (6)	C13—C12—C11	119.0 (2)
N3—Cu1—O1	91.43 (6)	C13—C12—H12	120.5
N3—Cu1—O2	90.26 (5)	C12—C13—C14	120.7 (2)
N3—Cu1—C1	91.32 (6)	C12—C13—H13	119.6
C1—O1—Cu1	82.56 (11)	C14—C13—H13	119.6
C1—O2—Cu1	96.52 (11)	C9—C14—C13	119.8 (2)
C8—O3—Cu1	106.27 (11)	C9—C14—H14	120.1
C15—N1—Cu1	120.40 (11)	C13—C14—H14	120.1
C19—N1—Cu1	120.98 (12)	N1—C15—C16	122.74 (16)
C19—N1—C15	118.47 (15)	N1—C15—H15	118.6
C20—N2—H2A	119.4 (16)	C16—C15—H15	118.6
C20—N2—H2B	121.7 (17)	C15—C16—C20	122.86 (15)
H2A—N2—H2B	118 (2)	C17—C16—C15	117.97 (16)
C21—N3—Cu1	120.20 (11)	C17—C16—C20	119.14 (16)
C21—N3—C25	118.42 (15)	C16—C17—H17	120.3
C25—N3—Cu1	121.34 (13)	C18—C17—C16	119.43 (17)
C26—N4—H4A	122.8 (16)	C18—C17—H17	120.3
C26—N4—H4B	119.5 (18)	C17—C18—C19	119.23 (17)
H4A—N4—H4B	118 (2)	C17—C18—H18	120.4
O1—C1—Cu1	68.16 (10)	C19—C18—H18	120.4
O1—C1—O2	121.15 (17)	N1—C19—C18	122.04 (17)
O1—C1—C2	120.21 (17)	N1—C19—H19	119.0
O2—C1—Cu1	53.00 (9)	C18—C19—H19	119.0
O2—C1—C2	118.64 (16)	O5—C20—N2	122.54 (17)
C2—C1—Cu1	171.55 (14)	O5—C20—C16	119.44 (16)
C3—C2—C1	121.54 (18)	N2—C20—C16	118.02 (15)
C3—C2—C7	119.6 (2)	N3—C21—C22	122.83 (15)
C7—C2—C1	118.8 (2)	N3—C21—H21	118.6
C2—C3—C4	119.3 (2)	C22—C21—H21	118.6
C2—C3—H3	120.4	C21—C22—C26	123.15 (15)
C4—C3—H3	120.4	C23—C22—C21	117.85 (17)
C3—C4—Cl1	119.5 (2)	C23—C22—C26	118.99 (16)
C5—C4—Cl1	119.32 (19)	C22—C23—H23	120.3
C5—C4—C3	121.1 (2)	C24—C23—C22	119.42 (18)
C4—C5—H5	120.4	C24—C23—H23	120.3
C6—C5—C4	119.1 (2)	C23—C24—H24	120.5
C6—C5—H5	120.4	C25—C24—C23	118.95 (17)
C5—C6—C7	120.6 (3)	C25—C24—H24	120.5
C5—C6—H6	119.7	N3—C25—C24	122.50 (18)
C7—C6—H6	119.7	N3—C25—H25	118.8
C2—C7—H7	119.9	C24—C25—H25	118.8
C6—C7—C2	120.2 (3)	O6—C26—N4	122.87 (19)
C6—C7—H7	119.9	O6—C26—C22	119.36 (17)
O3—C8—C9	116.61 (16)	N4—C26—C22	117.76 (16)
O2—Cu1—O1—C1	−0.68 (11)	Cu1—N3—C21—C22	177.25 (13)
O3—Cu1—O1—C1	176.18 (11)	C25—N3—C21—C22	−0.5 (3)
N1—Cu1—O1—C1	81.22 (12)	Cu1—N3—C25—C24	−176.47 (16)
N3—Cu1—O1—C1	−90.14 (12)	C21—N3—C25—C24	1.3 (3)
O1—Cu1—O2—C1	0.66 (10)	O1—C1—C2—C3	161.79 (19)
O3—Cu1—O2—C1	−12.1 (3)	O1—C1—C2—C7	−17.1 (3)
N1—Cu1—O2—C1	−102.89 (11)	O2—C1—C2—C3	−18.0 (3)
N3—Cu1—O2—C1	92.17 (11)	O2—C1—C2—C7	163.1 (2)
O1—Cu1—O3—C8	169.20 (11)	C1—C2—C3—C4	−178.91 (18)
O2—Cu1—O3—C8	−179.33 (19)	C7—C2—C3—C4	0.0 (3)
N1—Cu1—O3—C8	−88.86 (12)	C1—C2—C7—C6	−179.5 (2)
N3—Cu1—O3—C8	76.76 (12)	C3—C2—C7—C6	1.5 (4)
C1—Cu1—O3—C8	171.88 (11)	C2—C3—C4—Cl1	179.33 (16)
O1—Cu1—N1—C15	−126.37 (13)	C2—C3—C4—C5	−1.3 (3)
O1—Cu1—N1—C19	49.23 (15)	Cl1—C4—C5—C6	−179.5 (2)
O2—Cu1—N1—C15	−67.55 (14)	C3—C4—C5—C6	1.1 (4)
O2—Cu1—N1—C19	108.05 (15)	C4—C5—C6—C7	0.4 (5)
O3—Cu1—N1—C15	126.19 (14)	C2—C7—C6—C5	−1.7 (5)
O3—Cu1—N1—C19	−58.21 (15)	O3—C8—C9—C10	155.12 (18)
N3—Cu1—N1—C15	18.4 (3)	O3—C8—C9—C14	−24.5 (3)
N3—Cu1—N1—C19	−165.97 (19)	O4—C8—C9—C10	−23.5 (3)
C1—Cu1—N1—C15	−97.33 (14)	O4—C8—C9—C14	156.8 (2)
C1—Cu1—N1—C19	78.27 (15)	C8—C9—C10—C11	−176.52 (18)
O1—Cu1—N3—C21	128.70 (13)	C14—C9—C10—C11	3.1 (3)
O1—Cu1—N3—C25	−53.57 (15)	C8—C9—C14—C13	178.2 (2)
O2—Cu1—N3—C21	68.94 (13)	C10—C9—C14—C13	−1.4 (3)
O2—Cu1—N3—C25	−113.33 (15)	C9—C10—C11—Cl2	178.44 (17)
O3—Cu1—N3—C21	−124.39 (13)	C9—C10—C11—C12	−2.3 (3)
O3—Cu1—N3—C25	53.34 (15)	Cl2—C11—C12—C13	178.9 (2)
N1—Cu1—N3—C21	−16.8 (3)	C10—C11—C12—C13	−0.4 (4)
N1—Cu1—N3—C25	160.9 (2)	C14—C13—C12—C11	2.1 (4)
C1—Cu1—N3—C21	99.41 (13)	C9—C14—C13—C12	−1.2 (4)
C1—Cu1—N3—C25	−82.86 (15)	C17—C16—C15—N1	−0.1 (3)
O1—Cu1—C1—O2	−178.84 (18)	C20—C16—C15—N1	−177.97 (16)
O2—Cu1—C1—O1	178.84 (18)	C15—C16—C17—C18	2.7 (3)
O3—Cu1—C1—O1	−5.26 (15)	C20—C16—C17—C18	−179.32 (18)
O3—Cu1—C1—O2	175.90 (9)	C15—C16—C20—O5	155.40 (18)
N1—Cu1—C1—O1	−102.99 (12)	C15—C16—C20—N2	−25.1 (3)
N1—Cu1—C1—O2	78.17 (11)	C17—C16—C20—O5	−22.5 (3)
N3—Cu1—C1—O1	90.58 (12)	C17—C16—C20—N2	157.06 (18)
N3—Cu1—C1—O2	−88.26 (11)	C16—C17—C18—C19	−2.6 (3)
Cu1—O1—C1—O2	1.09 (17)	N1—C19—C18—C17	−0.2 (3)
Cu1—O1—C1—C2	−178.70 (16)	N3—C21—C22—C23	−0.8 (3)
Cu1—O2—C1—O1	−1.3 (2)	N3—C21—C22—C26	−179.89 (16)
Cu1—O2—C1—C2	178.53 (14)	C21—C22—C23—C24	1.5 (3)
Cu1—O3—C8—O4	−0.1 (2)	C26—C22—C23—C24	−179.42 (19)
Cu1—O3—C8—C9	−178.74 (13)	C21—C22—C26—O6	166.2 (2)
Cu1—N1—C15—C16	173.02 (13)	C21—C22—C26—N4	−14.9 (3)
C19—N1—C15—C16	−2.7 (3)	C23—C22—C26—O6	−12.9 (3)
Cu1—N1—C19—C18	−172.84 (16)	C23—C22—C26—N4	166.07 (19)
C15—N1—C19—C18	2.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2i	0.80 (2)	2.12 (2)	2.896 (2)	164 (2)
N2—H2B···O6ii	0.84 (3)	2.02 (3)	2.790 (2)	153 (2)
N4—H4A···O5i	0.83 (3)	2.01 (3)	2.817 (2)	164 (2)
N4—H4B···O4ii	0.81 (2)	2.05 (2)	2.836 (2)	162 (3)
C19—H19···O1iii	0.93	2.45	3.100 (2)	127
C21—H21···O5i	0.93	2.56	3.416 (2)	154
C24—H24···O3iv	0.93	2.59	3.475 (3)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O2i	0.80 (2)	2.12 (2)	2.896 (2)	164 (2)
N2—H2B⋯O6ii	0.84 (3)	2.02 (3)	2.790 (2)	153 (2)
N4—H4A⋯O5i	0.83 (3)	2.01 (3)	2.817 (2)	164 (2)
N4—H4B⋯O4ii	0.81 (2)	2.05 (2)	2.836 (2)	162 (3)
C19—H19⋯O1iii	0.93	2.45	3.100 (2)	127
C21—H21⋯O5i	0.93	2.56	3.416 (2)	154
C24—H24⋯O3iv	0.93	2.59	3.475 (3)	158

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .