[(4E,11E)-5,7,12,14-Tetra-benzyl-7,14-dimethyl-1,4,8,11-tetra-aza-cyclo-tetra-deca-4,11-diene]copper(II) bis(per-chlorate).

The complete cation in the title compound, [Cu(C(40)H(48)N(4))](ClO(4))(2), is generated by the operation of a crystallographic centre of inversion. The Cu(II) ion exists in a tetra-gonally distorted trans-N(4)O(2) coordination geometry defined by the four N atoms of the macrocyclic ligand and two weakly bound perchlorate-O atoms from two anions. The N-H atoms form intra-molecular N-H⋯O(perchlorate) hydrogen bonds. Disorder was resolved in the -CH(2)-NH- portion of the macrocycle with the major component having a site-occupancy factor of 0.570 (6).

Related literature

For background to the synthesis, characterization, kinetic studies and biological activities of 14-membered methyl-substituted tetra­aza­macrocyclic ligands, their N-substituted derivatives and their n class="Chemical">metal complexes, see: Hazari et al. (2008 ▶).

Experimental

Crystal data

[Cu(C40H48N4)](ClO4)2

M = 847.26

Monoclinic,

a = 10.1170 (3) Å

b = 16.6017 (4) Å

c = 11.9910 (3) Å

β = 108.818 (3)°

V = 1906.35 (9) Å3

Z = 2

Mo Kα radiation

μ = 0.77 mm−1

T = 100 K

0.30 × 0.25 × 0.20 mm

Data collection

Agilent Technologies SuperNova Dual diffractometer with Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.792, T max = 1.000

9806 measured reflections

4253 independent reflections

3707 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.145

S = 1.08

4253 reflections

251 parameters

15 restraints

H-atom parameters constrained

Δρmax = 0.64 e Å−3

Δρmin = −1.08 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and n class="Disease">DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811042796/hb6449sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811042796/hb6449Isup2.hkl

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

[Cu(C40H48N4)](ClO4)2	F(000) = 886
Mr = 847.26	Dx = 1.476 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4647 reflections
a = 10.1170 (3) Å	θ = 2.3–29.3°
b = 16.6017 (4) Å	µ = 0.77 mm−1
c = 11.9910 (3) Å	T = 100 K
β = 108.818 (3)°	Prism, light-purple
V = 1906.35 (9) Å3	0.30 × 0.25 × 0.20 mm
Z = 2

Agilent Technologies SuperNova Dual diffractometer with Atlas detector	4253 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	3707 reflections with I > 2σ(I)
Mirror	Rint = 0.024
Detector resolution: 10.4041 pixels mm-1	θmax = 27.5°, θmin = 2.3°
ω scan	h = −11→12
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −21→16
Tmin = 0.792, Tmax = 1.000	l = −15→15
9806 measured reflections

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0495P)2 + 4.3222P] where P = (Fo2 + 2Fc2)/3
4253 reflections	(Δ/σ)max < 0.001
251 parameters	Δρmax = 0.64 e Å−3
15 restraints	Δρmin = −1.08 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)
Cu	0.5000	0.5000	0.5000	0.0368 (2)
Cl1	0.85496 (8)	0.59569 (5)	0.64594 (7)	0.0320 (2)
O1	0.7221 (2)	0.59629 (15)	0.5522 (2)	0.0349 (6)
O2	0.8616 (3)	0.52613 (18)	0.7184 (3)	0.0520 (8)
O3	0.9641 (3)	0.5963 (2)	0.5963 (3)	0.0660 (10)
O4	0.8647 (3)	0.66693 (18)	0.7171 (2)	0.0492 (7)
N1	0.4748 (5)	0.4782 (3)	0.6587 (3)	0.0245 (10)	0.570 (6)
H1	0.4019	0.4462	0.6445	0.029*	0.570 (6)
N2	0.6240 (3)	0.40479 (15)	0.5342 (2)	0.0239 (5)
C1	0.6015 (5)	0.4282 (3)	0.7295 (4)	0.0277 (11)	0.570 (6)
H1A	0.6845	0.4631	0.7610	0.033*	0.570 (6)
H1B	0.5825	0.4011	0.7964	0.033*	0.570 (6)
C2	0.6264 (3)	0.36629 (19)	0.6456 (3)	0.0261 (7)
H2A	0.7181	0.3401	0.6825	0.031*	0.570 (6)
H2B	0.5533	0.3242	0.6294	0.031*	0.570 (6)
H2C	0.7195	0.3726	0.7058	0.031*	0.430 (6)
H2D	0.6056	0.3081	0.6334	0.031*	0.430 (6)
C3	0.7012 (3)	0.3815 (2)	0.4734 (3)	0.0257 (6)
C4	0.7948 (3)	0.3080 (2)	0.4994 (3)	0.0282 (7)
H4A	0.8072	0.2883	0.5800	0.034*
H4B	0.8878	0.3221	0.4943	0.034*
C5	0.7277 (3)	0.2425 (2)	0.4096 (3)	0.0281 (7)
C6	0.6296 (4)	0.1915 (2)	0.4294 (3)	0.0352 (8)
H6	0.6083	0.1955	0.5008	0.042*
C7	0.5617 (4)	0.1344 (2)	0.3456 (4)	0.0399 (9)
H7	0.4942	0.0999	0.3601	0.048*
C8	0.5919 (4)	0.1277 (2)	0.2413 (3)	0.0379 (8)
H8	0.5445	0.0892	0.1836	0.045*
C9	0.6922 (4)	0.1776 (2)	0.2218 (3)	0.0374 (8)
H9	0.7144	0.1728	0.1510	0.045*
C10	0.7604 (3)	0.2349 (2)	0.3059 (3)	0.0309 (7)
H10	0.8294	0.2687	0.2923	0.037*
C11	0.7003 (4)	0.4281 (2)	0.3652 (3)	0.0316 (7)
H11A	0.7518	0.3964	0.3226	0.038*
H11B	0.7527	0.4789	0.3911	0.038*
C12	0.5570 (4)	0.4493 (2)	0.2784 (3)	0.0303 (7)
C13	0.5729 (4)	0.4799 (2)	0.1621 (3)	0.0354 (8)
H13A	0.4791	0.4937	0.1074	0.042*
H13B	0.6288	0.5301	0.1784	0.042*
C14	0.4581 (3)	0.3778 (3)	0.2546 (3)	0.0391 (9)
H14A	0.3668	0.3939	0.2004	0.059*
H14B	0.4477	0.3591	0.3288	0.059*
H14C	0.4962	0.3341	0.2191	0.059*
C15	0.6410 (4)	0.42125 (19)	0.1011 (3)	0.0280 (7)
C16	0.5637 (3)	0.36046 (19)	0.0285 (3)	0.0268 (7)
H16	0.4664	0.3561	0.0163	0.032*
C17	0.6273 (3)	0.3066 (2)	−0.0260 (3)	0.0287 (7)
H17	0.5736	0.2650	−0.0742	0.034*
C18	0.7686 (4)	0.3126 (2)	−0.0109 (3)	0.0316 (7)
H18	0.8120	0.2756	−0.0485	0.038*
C19	0.8455 (4)	0.3731 (2)	0.0598 (3)	0.0366 (8)
H19	0.9421	0.3784	0.0698	0.044*
C20	0.7815 (3)	0.42676 (17)	0.1166 (2)	0.0331 (8)
H20	0.8358	0.4674	0.1665	0.040*
N1'	0.5452 (3)	0.49931 (17)	0.6741 (2)	0.0245 (10)	0.43
H1'	0.6332	0.5119	0.7103	0.029*	0.430 (6)
C1'	0.5178 (3)	0.40711 (17)	0.6846 (2)	0.0277 (11)	0.43
H1'1	0.5276	0.3925	0.7670	0.033*	0.430 (6)
H1'2	0.4230	0.3922	0.6333	0.033*	0.430 (6)

	U11	U22	U33	U12	U13	U23
Cu	0.0564 (4)	0.0281 (3)	0.0199 (3)	0.0258 (3)	0.0039 (3)	0.0029 (2)
Cl1	0.0177 (4)	0.0351 (4)	0.0413 (4)	−0.0034 (3)	0.0068 (3)	0.0122 (4)
O1	0.0232 (12)	0.0389 (14)	0.0379 (13)	0.0015 (10)	0.0034 (10)	−0.0016 (11)
O2	0.0465 (17)	0.0398 (15)	0.0623 (19)	−0.0023 (13)	0.0074 (14)	0.0250 (14)
O3	0.0303 (15)	0.092 (3)	0.087 (2)	−0.0031 (16)	0.0339 (16)	0.013 (2)
O4	0.0510 (17)	0.0442 (16)	0.0411 (15)	−0.0104 (13)	−0.0008 (13)	0.0021 (13)
N1	0.023 (2)	0.022 (2)	0.0222 (18)	0.0091 (17)	−0.0004 (19)	0.0010 (15)
N2	0.0225 (12)	0.0202 (12)	0.0252 (12)	0.0015 (10)	0.0024 (10)	0.0019 (10)
C1	0.025 (2)	0.034 (3)	0.026 (2)	0.013 (2)	0.0118 (18)	0.012 (2)
C2	0.0249 (15)	0.0244 (15)	0.0294 (16)	0.0057 (12)	0.0091 (13)	0.0081 (13)
C3	0.0182 (14)	0.0273 (16)	0.0282 (15)	−0.0013 (12)	0.0030 (12)	0.0037 (13)
C4	0.0182 (14)	0.0398 (18)	0.0266 (15)	0.0081 (13)	0.0075 (12)	0.0064 (14)
C5	0.0245 (15)	0.0303 (17)	0.0304 (16)	0.0158 (13)	0.0100 (13)	0.0096 (14)
C6	0.0354 (19)	0.0325 (18)	0.0418 (19)	0.0103 (15)	0.0183 (16)	0.0068 (16)
C7	0.038 (2)	0.0305 (18)	0.054 (2)	0.0072 (15)	0.0194 (18)	0.0029 (17)
C8	0.039 (2)	0.0277 (17)	0.042 (2)	0.0112 (15)	0.0063 (16)	0.0020 (16)
C9	0.042 (2)	0.039 (2)	0.0307 (17)	0.0218 (16)	0.0109 (15)	0.0106 (16)
C10	0.0245 (16)	0.0341 (18)	0.0361 (17)	0.0140 (13)	0.0127 (13)	0.0116 (15)
C11	0.0306 (17)	0.0320 (17)	0.0278 (16)	−0.0083 (14)	0.0033 (13)	0.0067 (14)
C12	0.0353 (18)	0.0277 (16)	0.0266 (15)	0.0127 (14)	0.0081 (13)	0.0019 (13)
C13	0.051 (2)	0.0247 (16)	0.0234 (16)	0.0058 (15)	0.0021 (15)	0.0004 (13)
C14	0.0204 (16)	0.066 (3)	0.0304 (17)	−0.0019 (16)	0.0080 (13)	−0.0073 (18)
C15	0.0372 (18)	0.0224 (15)	0.0204 (14)	0.0005 (13)	0.0035 (13)	0.0043 (12)
C16	0.0258 (15)	0.0268 (16)	0.0243 (15)	−0.0018 (13)	0.0030 (12)	0.0009 (13)
C17	0.0320 (17)	0.0268 (16)	0.0258 (15)	−0.0046 (13)	0.0072 (13)	−0.0018 (13)
C18	0.0318 (17)	0.0381 (19)	0.0268 (16)	−0.0006 (15)	0.0120 (14)	0.0002 (15)
C19	0.0298 (17)	0.051 (2)	0.0269 (16)	−0.0090 (16)	0.0058 (14)	−0.0010 (16)
C20	0.0376 (19)	0.0343 (18)	0.0235 (15)	−0.0129 (15)	0.0046 (14)	−0.0011 (14)
N1'	0.023 (2)	0.022 (2)	0.0222 (18)	0.0091 (17)	−0.0004 (19)	0.0010 (15)
C1'	0.025 (2)	0.034 (3)	0.026 (2)	0.013 (2)	0.0118 (18)	0.012 (2)

Cu—N1	2.032 (4)	C7—H7	0.9500
Cu—N2	1.977 (2)	C8—C9	1.386 (6)
Cu—N2i	1.977 (2)	C8—H8	0.9500
Cu—N1'i	1.988 (2)	C9—C10	1.396 (5)
Cu—N1'	1.988 (2)	C9—H9	0.9500
Cu—N1i	2.032 (4)	C10—H10	0.9500
Cu—O1i	2.662 (2)	C11—C12	1.528 (5)
Cu—O1	2.662 (2)	C11—H11A	0.9900
Cl1—O3	1.413 (3)	C11—H11B	0.9900
Cl1—O2	1.433 (3)	C12—N1i	1.510 (5)
Cl1—O4	1.443 (3)	C12—C14	1.519 (5)
Cl1—O1	1.447 (2)	C12—C13	1.541 (5)
N1—C12i	1.510 (5)	C12—N1'i	1.582 (4)
N1—C1	1.534 (4)	C13—C15	1.511 (5)
N1—H1	0.8800	C13—H13A	0.9900
N2—C3	1.287 (4)	C13—H13B	0.9900
N2—C2	1.475 (4)	C14—H14A	0.9800
C1—C2	1.515 (5)	C14—H14B	0.9800
C1—H1A	0.9900	C14—H14C	0.9800
C1—H1B	0.9900	C15—C20	1.376 (4)
C2—C1'	1.489 (4)	C15—C16	1.396 (4)
C2—H2A	0.9900	C16—C17	1.383 (5)
C2—H2B	0.9900	C16—H16	0.9500
C2—H2C	0.9900	C17—C18	1.385 (5)
C2—H2D	0.9900	C17—H17	0.9500
C3—C4	1.514 (4)	C18—C19	1.381 (5)
C3—C11	1.509 (4)	C18—H18	0.9500
C4—C5	1.527 (5)	C19—C20	1.400 (5)
C4—H4A	0.9900	C19—H19	0.9500
C4—H4B	0.9900	C20—H20	0.9500
C5—C6	1.383 (5)	N1'—C1'	1.5679
C5—C10	1.392 (4)	N1'—C12i	1.582 (4)
C6—C7	1.390 (5)	N1'—H1'	0.8800
C6—H6	0.9500	C1'—H1'1	0.9900
C7—C8	1.385 (5)	C1'—H1'2	0.9900
O1—Cu—N1	103.76 (15)	H4A—C4—H4B	108.3
O1—Cu—N2	90.01 (9)	C6—C5—C10	119.3 (3)
N2—Cu—N2i	180	C6—C5—C4	119.7 (3)
N2—Cu—N1'i	97.92 (11)	C10—C5—C4	121.0 (3)
N2i—Cu—N1'i	82.08 (11)	C5—C6—C7	120.5 (3)
N2—Cu—N1'	82.08 (11)	C5—C6—H6	119.7
N2i—Cu—N1'	97.92 (11)	C7—C6—H6	119.7
N1'i—Cu—N1'	180	C8—C7—C6	120.4 (4)
N2—Cu—N1i	94.20 (14)	C8—C7—H7	119.8
N2i—Cu—N1i	85.80 (14)	C6—C7—H7	119.8
N1'i—Cu—N1i	21.80 (14)	C7—C8—C9	119.3 (4)
N1'—Cu—N1i	158.20 (15)	C7—C8—H8	120.3
N1—Cu—N2	85.80 (14)	C9—C8—H8	120.3
N2i—Cu—N1	94.20 (14)	C10—C9—C8	120.3 (3)
N1'i—Cu—N1	158.20 (15)	C10—C9—H9	119.9
N1'—Cu—N1	21.80 (14)	C8—C9—H9	119.9
N1i—Cu—N1	180	C9—C10—C5	120.1 (3)
N2—Cu—O1i	89.99 (9)	C9—C10—H10	119.9
N2i—Cu—O1i	90.01 (9)	C5—C10—H10	119.9
N1'i—Cu—O1i	82.27 (10)	C3—C11—C12	116.4 (3)
N1'—Cu—O1i	97.73 (10)	C3—C11—H11A	108.2
N1i—Cu—O1i	103.76 (15)	C12—C11—H11A	108.2
N1—Cu—O1i	76.24 (15)	C3—C11—H11B	108.2
N2i—Cu—O1	89.99 (9)	C12—C11—H11B	108.2
N1'i—Cu—O1	97.73 (10)	H11A—C11—H11B	107.3
N1'—Cu—O1	82.27 (10)	N1i—C12—C14	118.9 (3)
N1i—Cu—O1	76.24 (15)	N1i—C12—C11	98.7 (3)
O1i—Cu—O1	180.0	C14—C12—C11	111.8 (3)
O3—Cl1—O2	111.7 (2)	N1i—C12—C13	106.9 (3)
O3—Cl1—O4	109.3 (2)	C14—C12—C13	110.0 (3)
O2—Cl1—O4	108.75 (18)	C11—C12—C13	109.8 (3)
O3—Cl1—O1	109.20 (19)	C14—C12—N1'i	91.3 (3)
O2—Cl1—O1	109.04 (16)	C11—C12—N1'i	117.8 (3)
O4—Cl1—O1	108.80 (16)	C13—C12—N1'i	114.8 (3)
Cl1—O1—Cu	132.88 (15)	C15—C13—C12	115.0 (3)
C12i—N1—C1	115.5 (3)	C15—C13—H13A	108.5
C12i—N1—Cu	115.9 (3)	C12—C13—H13A	108.5
C1—N1—Cu	106.3 (3)	C15—C13—H13B	108.5
C12i—N1—H1	106.1	C12—C13—H13B	108.5
C1—N1—H1	106.1	H13A—C13—H13B	107.5
Cu—N1—H1	106.1	C12—C14—H14A	109.5
C3—N2—C2	123.2 (3)	C12—C14—H14B	109.5
C3—N2—Cu	125.7 (2)	H14A—C14—H14B	109.5
C2—N2—Cu	110.97 (19)	C12—C14—H14C	109.5
C2—C1—N1	106.7 (3)	H14A—C14—H14C	109.5
C2—C1—H1A	110.4	H14B—C14—H14C	109.5
N1—C1—H1A	110.4	C20—C15—C16	118.6 (3)
C2—C1—H1B	110.4	C20—C15—C13	120.3 (3)
N1—C1—H1B	110.4	C16—C15—C13	121.1 (3)
H1A—C1—H1B	108.6	C17—C16—C15	120.6 (3)
N2—C2—C1'	106.8 (2)	C17—C16—H16	119.7
N2—C2—C1	110.5 (3)	C15—C16—H16	119.7
N2—C2—H2A	109.5	C16—C17—C18	120.6 (3)
C1'—C2—H2A	137.7	C16—C17—H17	119.7
C1—C2—H2A	109.5	C18—C17—H17	119.7
N2—C2—H2B	109.5	C19—C18—C17	119.1 (3)
C1'—C2—H2B	78.6	C19—C18—H18	120.5
C1—C2—H2B	109.5	C17—C18—H18	120.5
H2A—C2—H2B	108.1	C18—C19—C20	120.3 (3)
N2—C2—H2C	110.4	C18—C19—H19	119.9
C1'—C2—H2C	110.4	C20—C19—H19	119.9
C1—C2—H2C	76.6	C15—C20—C19	120.7 (3)
H2B—C2—H2C	133.9	C15—C20—H20	119.6
N2—C2—H2D	110.4	C19—C20—H20	119.6
C1'—C2—H2D	110.4	C1'—N1'—C12i	110.16 (17)
C1—C2—H2D	133.4	C1'—N1'—Cu	95.92 (8)
H2A—C2—H2D	76.1	C12i—N1'—Cu	114.78 (19)
H2C—C2—H2D	108.6	C1'—N1'—H1'	111.7
N2—C3—C4	125.4 (3)	C12i—N1'—H1'	111.7
N2—C3—C11	119.8 (3)	Cu—N1'—H1'	111.7
C4—C3—C11	114.8 (3)	C2—C1'—N1'	104.57 (17)
C3—C4—C5	108.8 (2)	C2—C1'—H1'1	110.8
C3—C4—H4A	109.9	N1'—C1'—H1'1	110.8
C5—C4—H4A	109.9	C2—C1'—H1'2	110.8
C3—C4—H4B	109.9	N1'—C1'—H1'2	110.8
C5—C4—H4B	109.9	H1'1—C1'—H1'2	108.9
O3—Cl1—O1—Cu	124.9 (2)	C3—C4—C5—C6	−85.3 (4)
O2—Cl1—O1—Cu	2.5 (3)	C3—C4—C5—C10	92.6 (3)
O4—Cl1—O1—Cu	−115.9 (2)	C10—C5—C6—C7	−1.5 (5)
N2—Cu—O1—Cl1	−43.1 (2)	C4—C5—C6—C7	176.4 (3)
N2i—Cu—O1—Cl1	136.9 (2)	C5—C6—C7—C8	0.3 (5)
N1'i—Cu—O1—Cl1	−141.1 (2)	C6—C7—C8—C9	0.9 (5)
N1'—Cu—O1—Cl1	38.9 (2)	C7—C8—C9—C10	−0.9 (5)
N1i—Cu—O1—Cl1	−137.4 (2)	C8—C9—C10—C5	−0.3 (5)
N1—Cu—O1—Cl1	42.6 (2)	C6—C5—C10—C9	1.5 (5)
N2—Cu—N1—C12i	151.7 (3)	C4—C5—C10—C9	−176.4 (3)
N2i—Cu—N1—C12i	−28.3 (3)	N2—C3—C11—C12	−48.0 (4)
N1'i—Cu—N1—C12i	−107.5 (5)	C4—C3—C11—C12	130.8 (3)
N1'—Cu—N1—C12i	72.5 (5)	C3—C11—C12—N1i	80.6 (4)
O1i—Cu—N1—C12i	−117.3 (3)	C3—C11—C12—C14	−45.5 (4)
O1—Cu—N1—C12i	62.7 (3)	C3—C11—C12—C13	−167.9 (3)
N2—Cu—N1—C1	21.9 (3)	C3—C11—C12—N1'i	58.3 (4)
N2i—Cu—N1—C1	−158.1 (3)	N1i—C12—C13—C15	164.9 (3)
N1'i—Cu—N1—C1	122.7 (4)	C14—C12—C13—C15	−64.7 (4)
N1'—Cu—N1—C1	−57.3 (4)	C11—C12—C13—C15	58.7 (4)
O1i—Cu—N1—C1	112.9 (3)	N1'i—C12—C13—C15	−165.9 (3)
O1—Cu—N1—C1	−67.1 (3)	C12—C13—C15—C20	−96.7 (4)
N1'i—Cu—N2—C3	30.0 (3)	C12—C13—C15—C16	83.1 (4)
N1'—Cu—N2—C3	−150.0 (3)	C20—C15—C16—C17	0.5 (5)
N1i—Cu—N2—C3	8.4 (3)	C13—C15—C16—C17	−179.3 (3)
N1—Cu—N2—C3	−171.6 (3)	C15—C16—C17—C18	−0.9 (5)
O1i—Cu—N2—C3	112.2 (3)	C16—C17—C18—C19	0.2 (5)
O1—Cu—N2—C3	−67.8 (3)	C17—C18—C19—C20	1.0 (5)
N1'i—Cu—N2—C2	−154.7 (2)	C16—C15—C20—C19	0.7 (4)
N1'—Cu—N2—C2	25.3 (2)	C13—C15—C20—C19	−179.5 (3)
N1i—Cu—N2—C2	−176.3 (2)	C18—C19—C20—C15	−1.5 (5)
N1—Cu—N2—C2	3.7 (2)	N2—Cu—N1'—C1'	−47.47 (8)
O1i—Cu—N2—C2	−72.5 (2)	N2i—Cu—N1'—C1'	132.53 (8)
O1—Cu—N2—C2	107.5 (2)	N1i—Cu—N1'—C1'	−128.9 (4)
C12i—N1—C1—C2	−172.4 (4)	N1—Cu—N1'—C1'	51.1 (4)
Cu—N1—C1—C2	−42.3 (4)	O1i—Cu—N1'—C1'	41.44 (6)
C3—N2—C2—C1'	−176.9 (3)	O1—Cu—N1'—C1'	−138.56 (6)
Cu—N2—C2—C1'	7.7 (3)	N2—Cu—N1'—C12i	−162.9 (2)
C3—N2—C2—C1	145.9 (3)	N2i—Cu—N1'—C12i	17.1 (2)
Cu—N2—C2—C1	−29.6 (3)	N1i—Cu—N1'—C12i	115.6 (4)
N1—C1—C2—N2	47.6 (5)	N1—Cu—N1'—C12i	−64.4 (4)
N1—C1—C2—C1'	−42.7 (3)	O1i—Cu—N1'—C12i	−74.0 (2)
C2—N2—C3—C4	5.9 (5)	O1—Cu—N1'—C12i	106.0 (2)
Cu—N2—C3—C4	−179.3 (2)	N2—C2—C1'—N1'	−48.2 (2)
C2—N2—C3—C11	−175.4 (3)	C1—C2—C1'—N1'	53.7 (4)
Cu—N2—C3—C11	−0.6 (4)	C12i—N1'—C1'—C2	−176.1 (3)
N2—C3—C4—C5	106.0 (4)	Cu—N1'—C1'—C2	64.78 (16)
C11—C3—C4—C5	−72.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.88	2.39	2.940 (5)	121
N1'—H1'···O2	0.88	2.29	3.104 (4)	153

Table 1

Selected bond lengths (Å)

Cu—N1	2.032 (4)
Cu—N2	1.977 (2)
Cu—O1	2.662 (2)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.88	2.39	2.940 (5)	121
N1′—H1′⋯O2	0.88	2.29	3.104 (4)	153

Symmetry code: (i) .