Tetra-kis(μ-3-chloro-benzoato-κ(2) O:O')bis-[(N,N-di-ethyl-nicotinamide-κN (1))copper(II)].

In the title centrosymmetric binuclear Cu(II) complex, [Cu2(C7H4ClO2)4(C10H14N2O)2], the two Cu(II) cations [Cu⋯Cu = 2.6314 (4) Å] are bridged by four 3-chloro-benzoate (CB) anions. The four carboxyl-ate O atoms around each Cu(II) cation form a distorted square-planar arrangement, the distorted square-pyramidal coordination geometry being completed by the pyridine N atom of the N,N-di-ethyl-nicotinamide (DENA) mol-ecule. The dihedral angle between the benzene ring and the carboxyl-ate group is 4.49 (11)° in one of the independent CB ligands and 12.00 (10)° in the other. The benzene rings of the independent CB ligands are oriented at a dihedral angle of 84.13 (6)°. In the crystal, weak C-H⋯O hydrogen bonds link the binuclear complex mol-ecules into supra-molecular chains running along [101].

Related literature

For niacin, see: Krishnamachari (1974 ▶). For N,N-di­ethyl­nicotinamide, see: Bigoli et al. (1972 ▶). For related structures, see: Speier & Fulop (1989 ▶); Usubaliev et al. (1980 ▶); Hökelek et al. (1995 ▶); Hökelek et al. (2009a ▶,b ▶,c ▶, 2011 ▶); Necefoğlu et al. (2010 ▶); Aydın et al. (2012 ▶).

Experimental

Crystal data

[Cu2(C7H4ClO2)4(C10H14N2O)2]

M = 1105.75

Monoclinic,

a = 12.6077 (4) Å

b = 16.7569 (5) Å

c = 12.1402 (4) Å

β = 99.647 (2)°

V = 2528.54 (14) Å3

Z = 2

Mo Kα radiation

μ = 1.11 mm−1

T = 296 K

0.35 × 0.25 × 0.20 mm

Data collection

Bruker SMART BREEZE CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2012 ▶) T min = 0.711, T max = 0.724

78293 measured reflections

5166 independent reflections

4702 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.083

S = 1.04

5166 reflections

309 parameters

85 restraints

H-atom parameters constrained

Δρmax = 0.70 e Å−3

Δρmin = −0.45 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/S1600536813017881/xu5716sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813017881/xu5716Isup2.hkl

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

[Cu2(C7H4ClO2)4(C10H14N2O)2]	F(000) = 1132
Mr = 1105.75	Dx = 1.452 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9380 reflections
a = 12.6077 (4) Å	θ = 2.5–29.9°
b = 16.7569 (5) Å	µ = 1.11 mm−1
c = 12.1402 (4) Å	T = 296 K
β = 99.647 (2)°	Block, green
V = 2528.54 (14) Å3	0.35 × 0.25 × 0.20 mm
Z = 2

Bruker SMART BREEZE CCD diffractometer	5166 independent reflections
Radiation source: fine-focus sealed tube	4702 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
φ and ω scans	θmax = 26.4°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −15→15
Tmin = 0.711, Tmax = 0.724	k = −20→20
78293 measured reflections	l = −15→15

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0449P)2 + 1.301P] where P = (Fo2 + 2Fc2)/3
5166 reflections	(Δ/σ)max = 0.002
309 parameters	Δρmax = 0.70 e Å−3
85 restraints	Δρmin = −0.45 e Å−3

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.

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 > 2sigma(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	0.580773 (15)	0.980853 (12)	0.578926 (15)	0.02838 (8)
Cl1	0.53514 (7)	0.79998 (5)	−0.03442 (5)	0.0761 (2)
Cl2	0.92843 (7)	1.31020 (5)	0.55213 (9)	0.1053 (3)
O1	0.63814 (10)	0.91758 (8)	0.46442 (10)	0.0409 (3)
O2	0.49984 (11)	0.95064 (9)	0.33241 (11)	0.0458 (3)
O3	0.64805 (10)	1.07718 (8)	0.52693 (11)	0.0422 (3)
O4	0.51122 (10)	1.10927 (8)	0.39242 (11)	0.0405 (3)
O5	1.04739 (13)	1.05214 (11)	0.83585 (15)	0.0658 (5)
N1	0.70894 (11)	0.96124 (10)	0.71646 (12)	0.0347 (3)
N2	1.06037 (13)	0.95243 (12)	0.71450 (16)	0.0502 (4)
C1	0.58602 (14)	0.91427 (10)	0.36697 (15)	0.0343 (4)
C2	0.62814 (15)	0.86185 (11)	0.28384 (15)	0.0373 (4)
C3	0.57253 (17)	0.85814 (12)	0.17511 (16)	0.0433 (4)
H3	0.5123	0.8900	0.1529	0.052*
C4	0.6080 (2)	0.80633 (14)	0.10029 (17)	0.0518 (5)
C5	0.6965 (2)	0.75909 (16)	0.1303 (2)	0.0661 (7)
H5	0.7186	0.7242	0.0790	0.079*
C6	0.7521 (2)	0.76385 (16)	0.2371 (2)	0.0678 (7)
H6	0.8127	0.7322	0.2581	0.081*
C7	0.71904 (18)	0.81551 (13)	0.31447 (19)	0.0493 (5)
H7	0.7579	0.8188	0.3865	0.059*
C8	0.60290 (14)	1.12046 (10)	0.44801 (14)	0.0319 (3)
C9	0.66516 (15)	1.19115 (11)	0.41815 (16)	0.0368 (4)
C10	0.75758 (17)	1.21469 (12)	0.48927 (19)	0.0463 (5)
H10	0.7814	1.1867	0.5549	0.056*
C11	0.81362 (19)	1.28015 (14)	0.4613 (2)	0.0620 (6)
C12	0.7809 (2)	1.32217 (15)	0.3639 (3)	0.0749 (8)
H12	0.8202	1.3659	0.3461	0.090*
C13	0.6896 (2)	1.29872 (15)	0.2938 (3)	0.0700 (7)
H13	0.6668	1.3267	0.2280	0.084*
C14	0.63081 (19)	1.23348 (13)	0.32036 (19)	0.0506 (5)
H14	0.5685	1.2182	0.2727	0.061*
C15	0.81050 (14)	0.97600 (11)	0.70628 (15)	0.0361 (4)
H15	0.8250	0.9911	0.6366	0.043*
C16	0.89570 (14)	0.97002 (11)	0.79394 (15)	0.0353 (4)
C17	0.87265 (15)	0.94853 (12)	0.89783 (15)	0.0412 (4)
H17	0.9273	0.9452	0.9595	0.049*
C18	0.76805 (17)	0.93223 (14)	0.90842 (16)	0.0468 (5)
H18	0.7512	0.9167	0.9770	0.056*
C19	0.68845 (15)	0.93925 (13)	0.81604 (16)	0.0425 (4)
H19	0.6178	0.9282	0.8237	0.051*
C20	1.00821 (15)	0.99464 (13)	0.78250 (17)	0.0429 (4)
C21	1.02241 (19)	0.87796 (16)	0.6595 (2)	0.0649 (7)
H211	0.9638	0.8574	0.6937	0.078*
H212	1.0803	0.8391	0.6717	0.078*
C22	0.9840 (3)	0.8867 (3)	0.5347 (3)	0.1069 (13)
H221	0.9232	0.9220	0.5219	0.160*
H222	0.9635	0.8354	0.5030	0.160*
H223	1.0410	0.9083	0.5003	0.160*
C23	1.17124 (19)	0.97631 (17)	0.7067 (2)	0.0660 (7)
H231	1.1878	0.9589	0.6353	0.079*
H232	1.1761	1.0341	0.7092	0.079*
C24	1.25301 (19)	0.9423 (2)	0.7983 (3)	0.0759 (8)
H241	1.2468	0.8852	0.7983	0.114*
H242	1.3238	0.9570	0.7864	0.114*
H243	1.2409	0.9630	0.8689	0.114*

	U11	U22	U33	U12	U13	U23
Cu1	0.02465 (11)	0.03345 (13)	0.02565 (12)	−0.00047 (7)	0.00020 (8)	−0.00112 (8)
Cl1	0.1050 (5)	0.0886 (5)	0.0378 (3)	−0.0216 (4)	0.0206 (3)	−0.0159 (3)
Cl2	0.0775 (5)	0.0876 (5)	0.1497 (8)	−0.0475 (4)	0.0157 (5)	−0.0400 (6)
O1	0.0411 (7)	0.0475 (8)	0.0346 (7)	0.0051 (6)	0.0077 (5)	−0.0066 (6)
O2	0.0428 (7)	0.0565 (8)	0.0370 (7)	0.0102 (6)	0.0033 (6)	−0.0131 (6)
O3	0.0388 (7)	0.0412 (7)	0.0432 (7)	−0.0097 (6)	−0.0030 (5)	0.0079 (6)
O4	0.0352 (7)	0.0427 (7)	0.0420 (7)	−0.0059 (5)	0.0018 (5)	0.0078 (6)
O5	0.0505 (9)	0.0705 (11)	0.0739 (11)	−0.0157 (8)	0.0032 (8)	−0.0230 (9)
N1	0.0292 (7)	0.0439 (8)	0.0293 (7)	0.0024 (6)	0.0000 (6)	0.0020 (6)
N2	0.0353 (8)	0.0583 (11)	0.0583 (11)	−0.0018 (8)	0.0114 (7)	−0.0050 (9)
C1	0.0339 (9)	0.0340 (9)	0.0370 (9)	−0.0054 (7)	0.0115 (7)	−0.0037 (7)
C2	0.0426 (10)	0.0342 (9)	0.0386 (9)	−0.0065 (7)	0.0175 (8)	−0.0034 (7)
C3	0.0485 (11)	0.0447 (11)	0.0396 (10)	−0.0073 (9)	0.0152 (8)	−0.0041 (8)
C4	0.0713 (14)	0.0516 (12)	0.0372 (10)	−0.0171 (11)	0.0227 (10)	−0.0097 (9)
C5	0.0912 (19)	0.0568 (14)	0.0586 (14)	0.0074 (13)	0.0371 (13)	−0.0140 (12)
C6	0.0772 (17)	0.0645 (16)	0.0668 (15)	0.0230 (13)	0.0275 (13)	−0.0051 (13)
C7	0.0532 (12)	0.0502 (12)	0.0475 (11)	0.0052 (9)	0.0175 (9)	−0.0023 (9)
C8	0.0336 (8)	0.0320 (8)	0.0313 (8)	−0.0012 (7)	0.0089 (7)	−0.0025 (7)
C9	0.0388 (9)	0.0325 (9)	0.0422 (10)	−0.0010 (7)	0.0160 (7)	−0.0024 (7)
C10	0.0464 (11)	0.0413 (10)	0.0532 (12)	−0.0095 (9)	0.0141 (9)	−0.0081 (9)
C11	0.0547 (13)	0.0458 (12)	0.0905 (18)	−0.0178 (10)	0.0269 (12)	−0.0182 (12)
C12	0.0827 (19)	0.0418 (12)	0.112 (2)	−0.0138 (12)	0.0507 (17)	0.0072 (14)
C13	0.0880 (19)	0.0502 (14)	0.0798 (18)	0.0066 (13)	0.0367 (15)	0.0238 (13)
C14	0.0570 (13)	0.0455 (11)	0.0523 (12)	0.0032 (9)	0.0178 (10)	0.0091 (9)
C15	0.0328 (9)	0.0463 (10)	0.0284 (8)	0.0019 (7)	0.0030 (7)	0.0019 (7)
C16	0.0298 (8)	0.0374 (9)	0.0368 (9)	0.0048 (7)	−0.0002 (7)	−0.0041 (7)
C17	0.0390 (10)	0.0477 (11)	0.0323 (9)	0.0063 (8)	−0.0071 (7)	0.0005 (8)
C18	0.0478 (11)	0.0610 (13)	0.0305 (9)	0.0047 (9)	0.0032 (8)	0.0074 (9)
C19	0.0341 (9)	0.0564 (12)	0.0366 (9)	−0.0003 (8)	0.0053 (7)	0.0065 (9)
C20	0.0325 (9)	0.0496 (11)	0.0430 (10)	0.0018 (8)	−0.0034 (8)	−0.0001 (9)
C21	0.0471 (12)	0.0638 (15)	0.0857 (17)	0.0030 (11)	0.0162 (12)	−0.0228 (13)
C22	0.087 (2)	0.141 (3)	0.086 (2)	0.022 (2)	−0.0043 (18)	−0.052 (2)
C23	0.0429 (12)	0.0784 (18)	0.0805 (18)	−0.0069 (11)	0.0214 (12)	0.0006 (14)
C24	0.0368 (12)	0.092 (2)	0.100 (2)	0.0002 (12)	0.0133 (12)	−0.0083 (17)

Cu1—Cu1i	2.6314 (4)	C9—C10	1.386 (3)
Cu1—O1	1.9791 (13)	C9—C14	1.388 (3)
Cu1—O2i	1.9688 (13)	C10—C11	1.378 (3)
Cu1—O3	1.9755 (13)	C10—H10	0.9300
Cu1—O4i	1.9703 (13)	C11—C12	1.378 (4)
Cu1—N1	2.1454 (14)	C12—H12	0.9300
Cl1—C4	1.740 (2)	C13—C12	1.369 (4)
Cl2—C11	1.741 (3)	C13—H13	0.9300
O1—C1	1.255 (2)	C14—C13	1.388 (3)
O2—C1	1.255 (2)	C14—H14	0.9300
O2—Cu1i	1.9688 (13)	C15—H15	0.9300
O3—C8	1.259 (2)	C16—C15	1.383 (2)
O4—Cu1i	1.9703 (13)	C16—C20	1.506 (3)
O4—C8	1.251 (2)	C17—C16	1.388 (3)
O5—C20	1.218 (3)	C17—C18	1.374 (3)
N1—C15	1.330 (2)	C17—H17	0.9300
N1—C19	1.330 (2)	C18—H18	0.9300
N2—C20	1.340 (3)	C19—C18	1.379 (3)
N2—C21	1.458 (3)	C19—H19	0.9300
N2—C23	1.472 (3)	C21—C22	1.519 (4)
C1—C2	1.500 (2)	C21—H211	0.9700
C2—C3	1.388 (3)	C21—H212	0.9700
C2—C7	1.383 (3)	C22—H221	0.9600
C3—C4	1.384 (3)	C22—H222	0.9600
C3—H3	0.9300	C22—H223	0.9600
C4—C5	1.367 (4)	C23—C24	1.496 (4)
C5—C6	1.369 (4)	C23—H232	0.9700
C5—H5	0.9300	C23—H231	0.9700
C6—H6	0.9300	C24—H241	0.9600
C7—C6	1.392 (3)	C24—H242	0.9600
C7—H7	0.9300	C24—H243	0.9600
C8—C9	1.499 (2)
O1—Cu1—Cu1i	87.05 (4)	C10—C11—Cl2	118.7 (2)
O1—Cu1—N1	98.53 (6)	C10—C11—C12	121.7 (2)
O2i—Cu1—Cu1i	81.29 (4)	C12—C11—Cl2	119.57 (19)
O2i—Cu1—O1	168.33 (6)	C11—C12—H12	120.5
O2i—Cu1—O3	89.25 (6)	C13—C12—C11	119.1 (2)
O2i—Cu1—O4i	88.70 (6)	C13—C12—H12	120.5
O2i—Cu1—N1	93.11 (6)	C12—C13—C14	120.5 (3)
O3—Cu1—Cu1i	83.65 (4)	C12—C13—H13	119.8
O3—Cu1—O1	89.21 (6)	C14—C13—H13	119.8
O3—Cu1—N1	93.79 (6)	C9—C14—C13	119.9 (2)
O4i—Cu1—Cu1i	84.77 (4)	C9—C14—H14	120.0
O4i—Cu1—O1	90.49 (6)	C13—C14—H14	120.0
O4i—Cu1—O3	168.41 (5)	N1—C15—C16	123.41 (17)
O4i—Cu1—N1	97.71 (6)	N1—C15—H15	118.3
N1—Cu1—Cu1i	173.85 (4)	C16—C15—H15	118.3
C1—O1—Cu1	119.39 (12)	C15—C16—C17	117.64 (17)
C1—O2—Cu1i	126.70 (12)	C15—C16—C20	122.09 (17)
C8—O3—Cu1	123.38 (11)	C17—C16—C20	119.91 (16)
C8—O4—Cu1i	122.52 (12)	C16—C17—H17	120.4
C15—N1—Cu1	120.69 (12)	C18—C17—C16	119.14 (16)
C19—N1—Cu1	120.94 (12)	C18—C17—H17	120.4
C19—N1—C15	118.21 (15)	C17—C18—C19	119.09 (18)
C20—N2—C21	125.21 (18)	C17—C18—H18	120.5
C20—N2—C23	117.7 (2)	C19—C18—H18	120.5
C21—N2—C23	116.48 (19)	N1—C19—C18	122.49 (18)
O1—C1—O2	125.52 (16)	N1—C19—H19	118.8
O1—C1—C2	118.14 (16)	C18—C19—H19	118.8
O2—C1—C2	116.33 (16)	O5—C20—N2	123.2 (2)
C3—C2—C1	119.11 (17)	O5—C20—C16	118.15 (19)
C7—C2—C1	121.25 (17)	N2—C20—C16	118.64 (18)
C7—C2—C3	119.61 (18)	N2—C21—C22	113.6 (3)
C2—C3—H3	120.5	N2—C21—H211	108.9
C4—C3—C2	119.0 (2)	N2—C21—H212	108.9
C4—C3—H3	120.5	C22—C21—H211	108.9
C3—C4—Cl1	118.5 (2)	C22—C21—H212	108.9
C5—C4—Cl1	119.61 (17)	H211—C21—H212	107.7
C5—C4—C3	121.8 (2)	C21—C22—H221	109.5
C4—C5—C6	119.0 (2)	C21—C22—H222	109.5
C4—C5—H5	120.5	C21—C22—H223	109.5
C6—C5—H5	120.5	H221—C22—H222	109.5
C5—C6—C7	120.8 (2)	H221—C22—H223	109.5
C5—C6—H6	119.6	H222—C22—H223	109.5
C7—C6—H6	119.6	N2—C23—C24	113.1 (2)
C2—C7—C6	119.8 (2)	N2—C23—H232	109.0
C2—C7—H7	120.1	N2—C23—H231	109.0
C6—C7—H7	120.1	C24—C23—H232	109.0
O3—C8—C9	116.81 (15)	C24—C23—H231	109.0
O4—C8—O3	125.68 (16)	H232—C23—H231	107.8
O4—C8—C9	117.52 (16)	C23—C24—H243	109.5
C10—C9—C8	119.60 (18)	C23—C24—H242	109.5
C10—C9—C14	119.75 (19)	C23—C24—H241	109.5
C14—C9—C8	120.64 (18)	H243—C24—H242	109.5
C9—C10—H10	120.5	H243—C24—H241	109.5
C11—C10—C9	119.0 (2)	H242—C24—H241	109.5
C11—C10—H10	120.5
Cu1i—Cu1—O1—C1	−1.49 (13)	O1—C1—C2—C3	−179.12 (17)
O2i—Cu1—O1—C1	−2.7 (4)	O1—C1—C2—C7	2.9 (3)
O3—Cu1—O1—C1	−85.17 (14)	O2—C1—C2—C3	1.7 (3)
O4i—Cu1—O1—C1	83.25 (14)	O2—C1—C2—C7	−176.27 (18)
N1—Cu1—O1—C1	−178.88 (13)	C1—C2—C3—C4	−176.33 (17)
Cu1i—Cu1—O3—C8	−0.31 (14)	C7—C2—C3—C4	1.7 (3)
O1—Cu1—O3—C8	86.81 (15)	C3—C2—C7—C6	−1.9 (3)
O2i—Cu1—O3—C8	−81.63 (15)	C1—C2—C7—C6	176.0 (2)
O4i—Cu1—O3—C8	−1.8 (4)	C2—C3—C4—Cl1	178.00 (15)
N1—Cu1—O3—C8	−174.70 (14)	C2—C3—C4—C5	−0.4 (3)
O1—Cu1—N1—C15	52.96 (15)	Cl1—C4—C5—C6	−179.0 (2)
O1—Cu1—N1—C19	−131.61 (16)	C3—C4—C5—C6	−0.7 (4)
O2i—Cu1—N1—C15	−126.27 (15)	C4—C5—C6—C7	0.4 (4)
O2i—Cu1—N1—C19	49.16 (16)	C2—C7—C6—C5	0.9 (4)
O3—Cu1—N1—C15	−36.82 (15)	O3—C8—C9—C10	−12.2 (2)
O3—Cu1—N1—C19	138.61 (16)	O3—C8—C9—C14	168.16 (18)
O4i—Cu1—N1—C15	144.62 (14)	O4—C8—C9—C10	168.11 (17)
O4i—Cu1—N1—C19	−39.95 (16)	O4—C8—C9—C14	−11.5 (3)
Cu1—O1—C1—O2	2.8 (3)	C8—C9—C10—C11	−179.51 (18)
Cu1—O1—C1—C2	−176.35 (11)	C14—C9—C10—C11	0.1 (3)
Cu1i—O2—C1—O1	−2.6 (3)	C8—C9—C14—C13	−179.86 (19)
Cu1i—O2—C1—C2	176.52 (12)	C10—C9—C14—C13	0.5 (3)
Cu1—O3—C8—O4	0.1 (3)	C9—C10—C11—Cl2	179.02 (16)
Cu1—O3—C8—C9	−179.54 (11)	C9—C10—C11—C12	−0.7 (3)
Cu1i—O4—C8—O3	0.3 (3)	C10—C11—C12—C13	0.7 (4)
Cu1i—O4—C8—C9	179.96 (11)	Cl2—C11—C12—C13	−179.1 (2)
Cu1—N1—C15—C16	175.23 (14)	C14—C13—C12—C11	0.0 (4)
C19—N1—C15—C16	−0.3 (3)	C9—C14—C13—C12	−0.6 (4)
Cu1—N1—C19—C18	−174.76 (16)	C17—C16—C15—N1	−0.9 (3)
C15—N1—C19—C18	0.8 (3)	C20—C16—C15—N1	−174.04 (18)
C21—N2—C20—O5	172.2 (2)	C15—C16—C20—O5	113.2 (2)
C21—N2—C20—C16	−7.7 (3)	C15—C16—C20—N2	−66.8 (3)
C23—N2—C20—O5	1.4 (3)	C17—C16—C20—O5	−59.7 (3)
C23—N2—C20—C16	−178.50 (19)	C17—C16—C20—N2	120.2 (2)
C20—N2—C21—C22	107.6 (3)	C18—C17—C16—C15	1.7 (3)
C23—N2—C21—C22	−81.5 (3)	C18—C17—C16—C20	174.99 (19)
C20—N2—C23—C24	83.6 (3)	C16—C17—C18—C19	−1.3 (3)
C21—N2—C23—C24	−88.0 (3)	N1—C19—C18—C17	0.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···O5ii	0.93	2.45	3.221 (3)	140

Table 1

Selected bond lengths (Å)

Cu1—O1	1.9791 (13)
Cu1—O2i	1.9688 (13)
Cu1—O3	1.9755 (13)
Cu1—O4i	1.9703 (13)
Cu1—N1	2.1454 (14)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17⋯O5ii	0.93	2.45	3.221 (3)	140

Symmetry code: (ii) .