Diaqua-[μ-11,23-di-tert-butyl-3,7,15,19-tetra-azatricyclo-[19.3.1.1(9,13)]tetra-cosa-1(25),2,6,9,11,13(26),14,19,21,23-do-decaene-25,26-diolato-κ(4)N(3),N(7),O(25),O(26):κ(4)N(15),N(19),O(25),O(26)]dicopper(II) bis-(perchlorate).

In the dinuclear title complex, [Cu(2)(C(30)H(38)N(4)O(2))(H(2)O)(2)](ClO(4))(2), the coordination cation has crystallographically imposed twofold rotational symmetry. The Cu(II) ion is five-coordinated by two N and two O atoms from the macrocylic ligand and one O atom from a water mol-ecule, forming a square-pyramidal N(2)O(3) geometry with the water mol-ecule in the apical position. The distance between the two Cu(II) atoms is 3.0930 (5) Å. Hydrogen bonds between water mol-ecules and between water mol-ecules and perchlorate anions assemble two cations and four anions into discrete supermolecules of S(4) symmetry. Intramolecular O-H⋯N hydrogen bonds are also observed. The perchlorate anion and the tert-butyl group are disordered over two positions, with occupancies of the major positions of 0.527 (11) and 0.592 (9), respectively.

Related literature

For the synthesis of the magnesium precursor, see: Mohanta et al. (1997 ▶). For the synthesis of 4-tert-butyl-2,6-diformyl­phenol, see: Lindoy et al. (1998 ▶). For similar copper(II) and nickel(II) complexes, see: Bai et al. (2007 ▶); Chen et al. (2005 ▶); Nanda et al. (1994 ▶). For the preparation of similar macrocyclic ligands, see: Thompson et al. (1996 ▶); Pilkington & Robson (1970 ▶); Zhou et al. (2005 ▶).

Experimental

Crystal data

[Cu2(C30H38N4O2)(H2O)2](ClO4)2

M = 848.66

Tetragonal,

a = 18.9013 (4) Å

c = 9.9174 (4) Å

V = 3543.08 (18) Å3

Z = 4

Mo Kα radiation

μ = 1.42 mm−1

T = 296 K

0.38 × 0.36 × 0.32 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.615, T max = 0.660

19006 measured reflections

3489 independent reflections

2942 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.115

S = 1.02

3489 reflections

298 parameters

125 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.47 e Å−3

Δρmin = −0.33 e Å−3

Absolute structure: Flack (1983 ▶), 1527 Friedel pairs

Flack parameter: 0.31 (3)

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812031248/gk2504sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812031248/gk2504Isup2.hkl

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

[Cu2(C30H38N4O2)(H2O)2](ClO4)2	Dx = 1.591 Mg m−3
Mr = 848.66	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P421c	Cell parameters from 7958 reflections
Hall symbol: P-42 n	θ = 2.3–29.4°
a = 18.9013 (4) Å	µ = 1.42 mm−1
c = 9.9174 (4) Å	T = 296 K
V = 3543.08 (18) Å3	Block, blue
Z = 4	0.38 × 0.36 × 0.32 mm
F(000) = 1752

Bruker APEXII CCD diffractometer	3489 independent reflections
Radiation source: fine-focus sealed tube	2942 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
phi and ω scans	θmax = 26.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −18→23
Tmin = 0.615, Tmax = 0.660	k = −22→23
19006 measured reflections	l = −12→9

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.115	w = 1/[σ2(Fo2) + (0.0615P)2 + 4.6836P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
3489 reflections	Δρmax = 0.47 e Å−3
298 parameters	Δρmin = −0.33 e Å−3
125 restraints	Absolute structure: Flack (1983), 1527 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.31 (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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cu1	0.08182 (2)	0.99986 (3)	0.18030 (5)	0.03063 (16)
O1	−0.00045 (19)	0.93667 (12)	0.1690 (3)	0.0329 (6)
O2	0.0833 (2)	0.9539 (2)	0.4388 (5)	0.0614 (10)
N1	0.14955 (18)	0.92478 (19)	0.1474 (4)	0.0314 (9)
N2	0.14970 (19)	1.0758 (2)	0.2082 (4)	0.0389 (10)
C1	0.1312 (2)	1.1411 (2)	0.2233 (5)	0.0361 (10)
H1	0.1678	1.1728	0.2406	0.043*
C2	0.2279 (3)	1.0650 (3)	0.2171 (8)	0.0657 (19)
H2A'	0.2493	1.0819	0.1343	0.079*
H2B'	0.2461	1.0936	0.2904	0.079*
C3	0.2500 (2)	0.9908 (3)	0.2390 (6)	0.0504 (13)
H3A	0.2311	0.9744	0.3244	0.061*
H3B	0.3012	0.9889	0.2446	0.061*
C4	0.2254 (2)	0.9415 (3)	0.1278 (5)	0.0431 (11)
H4A	0.2322	0.9639	0.0408	0.052*
H4B	0.2530	0.8983	0.1296	0.052*
C5	0.1332 (2)	0.8591 (2)	0.1536 (5)	0.0347 (10)
H5	0.1698	0.8272	0.1384	0.042*
C6	0.0651 (2)	0.8288 (2)	0.1813 (5)	0.0318 (9)
C7	0.0649 (2)	0.7551 (2)	0.2042 (5)	0.0398 (11)
H7	0.1073	0.7305	0.1974	0.048*
C8	0.0046 (3)	0.71818 (19)	0.2360 (4)	0.0393 (9)
C9	−0.0578 (3)	0.7557 (2)	0.2404 (5)	0.0394 (11)
H9	−0.0995	0.7316	0.2599	0.047*
C10	−0.0611 (3)	0.8288 (2)	0.2168 (5)	0.0330 (11)
C11	0.0005 (3)	0.86673 (17)	0.1894 (4)	0.0297 (7)
C12	0.0062 (3)	0.6385 (2)	0.2598 (5)	0.0538 (12)
C13	0.0775 (4)	0.6074 (4)	0.2618 (11)	0.059 (3)	0.592 (9)
H13A	0.0741	0.5574	0.2771	0.089*	0.592 (9)
H13B	0.1047	0.6287	0.3328	0.089*	0.592 (9)
H13C	0.1004	0.6159	0.1768	0.089*	0.592 (9)
C14	−0.0277 (6)	0.6227 (6)	0.3911 (9)	0.085 (4)	0.592 (9)
H14A	−0.0269	0.5725	0.4067	0.127*	0.592 (9)
H14B	−0.0759	0.6389	0.3898	0.127*	0.592 (9)
H14C	−0.0024	0.6463	0.4619	0.127*	0.592 (9)
C15	−0.0368 (6)	0.6024 (6)	0.1554 (11)	0.086 (4)	0.592 (9)
H15A	−0.0357	0.5522	0.1705	0.129*	0.592 (9)
H15B	−0.0178	0.6127	0.0678	0.129*	0.592 (9)
H15C	−0.0848	0.6188	0.1603	0.129*	0.592 (9)
C13'	0.0409 (8)	0.6032 (9)	0.1429 (13)	0.084 (6)	0.408 (9)
H13D	0.0419	0.5530	0.1577	0.126*	0.408 (9)
H13E	0.0883	0.6206	0.1335	0.126*	0.408 (9)
H13F	0.0147	0.6132	0.0622	0.126*	0.408 (9)
C14'	0.0491 (8)	0.6226 (10)	0.3793 (13)	0.085 (6)	0.408 (9)
H14D	0.0500	0.5724	0.3938	0.127*	0.408 (9)
H14E	0.0289	0.6455	0.4567	0.127*	0.408 (9)
H14F	0.0964	0.6395	0.3657	0.127*	0.408 (9)
C15'	−0.0633 (5)	0.6048 (7)	0.2754 (15)	0.064 (4)	0.408 (9)
H15D	−0.0572	0.5550	0.2896	0.096*	0.408 (9)
H15E	−0.0908	0.6124	0.1953	0.096*	0.408 (9)
H15F	−0.0873	0.6251	0.3514	0.096*	0.408 (9)
Cl1	0.22950 (8)	0.78567 (9)	0.46056 (14)	0.0669 (4)
O3	0.1844 (6)	0.8458 (5)	0.4620 (12)	0.086 (4)	0.527 (11)
O4	0.2055 (8)	0.7328 (7)	0.5596 (13)	0.160 (7)	0.527 (11)
O5	0.2295 (6)	0.7511 (6)	0.3334 (8)	0.102 (4)	0.527 (11)
O6	0.2988 (5)	0.8071 (8)	0.4988 (16)	0.153 (6)	0.527 (11)
O3'	0.1632 (4)	0.8212 (7)	0.4726 (13)	0.082 (4)	0.473 (11)
O4'	0.2672 (7)	0.8119 (8)	0.3419 (11)	0.142 (7)	0.473 (11)
O5'	0.2189 (8)	0.7114 (4)	0.4411 (19)	0.164 (7)	0.473 (11)
O6'	0.2725 (5)	0.7960 (6)	0.5766 (10)	0.084 (4)	0.473 (11)
H2B	0.054 (4)	0.932 (4)	0.482 (8)	0.101*
H2A	0.115 (3)	0.937 (3)	0.395 (3)	0.101*

	U11	U22	U33	U12	U13	U23
Cu1	0.0211 (2)	0.0202 (2)	0.0506 (3)	0.0005 (3)	−0.00050 (19)	−0.0018 (3)
O1	0.0256 (12)	0.0176 (11)	0.0556 (16)	0.0010 (15)	0.002 (2)	0.0020 (10)
O2	0.051 (2)	0.056 (2)	0.078 (3)	0.0051 (18)	0.013 (2)	−0.008 (2)
N1	0.0249 (17)	0.0275 (18)	0.042 (2)	0.0022 (15)	0.0023 (15)	−0.0005 (15)
N2	0.0228 (17)	0.031 (2)	0.063 (3)	−0.0002 (15)	−0.0023 (17)	−0.0026 (18)
C1	0.030 (2)	0.027 (2)	0.052 (3)	−0.0061 (17)	−0.004 (2)	−0.0028 (19)
C2	0.026 (2)	0.037 (3)	0.134 (6)	0.001 (2)	−0.013 (3)	−0.016 (3)
C3	0.027 (2)	0.049 (3)	0.076 (3)	0.002 (2)	−0.009 (2)	−0.003 (3)
C4	0.030 (2)	0.033 (2)	0.066 (3)	0.0016 (19)	0.006 (2)	−0.006 (2)
C5	0.029 (2)	0.029 (2)	0.046 (3)	0.0074 (18)	0.0041 (19)	0.0023 (19)
C6	0.034 (2)	0.019 (2)	0.043 (2)	0.0015 (17)	−0.001 (2)	0.0013 (19)
C7	0.036 (2)	0.024 (2)	0.060 (3)	0.0062 (19)	−0.002 (2)	0.003 (2)
C8	0.046 (2)	0.0224 (17)	0.049 (2)	0.001 (2)	0.000 (2)	0.0035 (16)
C9	0.047 (3)	0.022 (2)	0.049 (3)	−0.006 (2)	0.004 (2)	0.0032 (19)
C10	0.034 (3)	0.022 (2)	0.043 (3)	−0.0023 (17)	0.0053 (19)	0.0008 (17)
C11	0.0305 (17)	0.0183 (15)	0.040 (2)	0.002 (2)	−0.004 (2)	0.0004 (14)
C12	0.054 (3)	0.0230 (18)	0.085 (3)	0.001 (2)	−0.005 (3)	0.010 (2)
C13	0.062 (4)	0.031 (4)	0.085 (5)	0.013 (3)	0.003 (4)	0.010 (3)
C14	0.097 (6)	0.066 (5)	0.091 (6)	0.013 (4)	0.012 (4)	0.020 (4)
C15	0.095 (6)	0.061 (5)	0.102 (6)	−0.006 (4)	−0.015 (5)	−0.001 (4)
C13'	0.092 (8)	0.068 (7)	0.092 (8)	−0.002 (5)	0.011 (5)	−0.008 (5)
C14'	0.088 (7)	0.075 (7)	0.091 (7)	−0.001 (5)	−0.008 (5)	0.015 (5)
C15'	0.070 (6)	0.048 (6)	0.075 (6)	−0.007 (4)	0.002 (5)	0.007 (4)
Cl1	0.0723 (9)	0.0795 (10)	0.0488 (7)	0.0325 (8)	−0.0097 (7)	−0.0036 (7)
O3	0.088 (5)	0.075 (5)	0.095 (5)	0.031 (4)	−0.004 (4)	0.003 (4)
O4	0.169 (8)	0.154 (8)	0.157 (8)	0.000 (5)	0.014 (5)	0.012 (5)
O5	0.105 (6)	0.110 (6)	0.091 (5)	0.033 (4)	0.002 (4)	−0.021 (4)
O6	0.142 (8)	0.159 (8)	0.157 (8)	−0.004 (5)	−0.012 (5)	0.004 (5)
O3'	0.076 (6)	0.082 (6)	0.087 (6)	0.019 (4)	0.002 (4)	−0.001 (4)
O4'	0.137 (8)	0.151 (8)	0.137 (8)	0.011 (5)	0.013 (5)	0.013 (5)
O5'	0.169 (9)	0.151 (8)	0.173 (9)	−0.002 (5)	0.002 (5)	−0.011 (5)
O6'	0.072 (5)	0.098 (6)	0.082 (5)	0.022 (4)	−0.026 (4)	−0.008 (4)

Cu1—N1	1.939 (4)	C10—C1i	1.444 (6)
Cu1—N2	1.945 (4)	C12—C15'	1.467 (8)
Cu1—O1i	1.954 (3)	C12—C14'	1.468 (8)
Cu1—O1	1.964 (3)	C12—C13	1.471 (7)
Cu1—O2	2.707 (5)	C12—C14	1.482 (7)
O1—C11	1.338 (4)	C12—C15	1.482 (8)
O1—Cu1i	1.954 (3)	C12—C13'	1.489 (9)
O2—H2B	0.82 (2)	C13—H13A	0.9600
O2—H2A	0.81 (2)	C13—H13B	0.9600
N1—C5	1.282 (6)	C13—H13C	0.9600
N1—C4	1.481 (6)	C14—H14A	0.9600
N2—C1	1.291 (6)	C14—H14B	0.9600
N2—C2	1.494 (6)	C14—H14C	0.9600
C1—C10i	1.444 (6)	C15—H15A	0.9600
C1—H1	0.9300	C15—H15B	0.9600
C2—C3	1.480 (7)	C15—H15C	0.9600
C2—H2A'	0.9700	C13'—H13D	0.9600
C2—H2B'	0.9700	C13'—H13E	0.9600
C3—C4	1.516 (7)	C13'—H13F	0.9600
C3—H3A	0.9700	C14'—H14D	0.9600
C3—H3B	0.9700	C14'—H14E	0.9600
C4—H4A	0.9700	C14'—H14F	0.9600
C4—H4B	0.9700	C15'—H15D	0.9600
C5—C6	1.435 (6)	C15'—H15E	0.9600
C5—H5	0.9300	C15'—H15F	0.9600
C6—C7	1.411 (6)	Cl1—O5	1.421 (6)
C6—C11	1.418 (6)	Cl1—O3	1.421 (6)
C7—C8	1.372 (7)	Cl1—O6'	1.422 (7)
C7—H7	0.9300	Cl1—O6	1.422 (7)
C8—C9	1.378 (7)	Cl1—O3'	1.426 (7)
C8—C12	1.525 (5)	Cl1—O5'	1.431 (7)
C9—C10	1.403 (6)	Cl1—O4'	1.462 (8)
C9—H9	0.9300	Cl1—O4	1.472 (8)
C10—C11	1.395 (7)
N1—Cu1—N2	97.38 (14)	C13—C12—C14	107.7 (6)
N1—Cu1—O1i	163.64 (15)	C13—C12—C15	109.2 (6)
N2—Cu1—O1i	94.27 (13)	C14—C12—C15	106.5 (6)
N1—Cu1—O1	93.91 (13)	C15'—C12—C13'	106.4 (7)
N2—Cu1—O1	168.30 (15)	C14'—C12—C13'	107.1 (7)
O1i—Cu1—O1	75.33 (11)	C15'—C12—C8	115.3 (7)
C11—O1—Cu1i	127.5 (3)	C14'—C12—C8	109.8 (8)
C11—O1—Cu1	125.6 (3)	C13—C12—C8	114.4 (5)
Cu1i—O1—Cu1	104.28 (11)	C14—C12—C8	109.1 (6)
H2B—O2—H2A	125 (8)	C15—C12—C8	109.7 (6)
C5—N1—C4	116.5 (4)	C13'—C12—C8	109.3 (8)
C5—N1—Cu1	122.8 (3)	C12—C13—H13A	109.5
C4—N1—Cu1	120.3 (3)	C12—C13—H13B	109.5
C1—N2—C2	113.0 (4)	H13A—C13—H13B	109.5
C1—N2—Cu1	122.9 (3)	C12—C13—H13C	109.5
C2—N2—Cu1	124.1 (3)	H13A—C13—H13C	109.5
N2—C1—C10i	128.3 (4)	H13B—C13—H13C	109.5
N2—C1—H1	115.9	C12—C14—H14A	109.5
C10i—C1—H1	115.9	C12—C14—H14B	109.5
C3—C2—N2	114.7 (4)	H14A—C14—H14B	109.5
C3—C2—H2A'	108.6	C12—C14—H14C	109.5
N2—C2—H2A'	108.6	H14A—C14—H14C	109.5
C3—C2—H2B'	108.6	H14B—C14—H14C	109.5
N2—C2—H2B'	108.6	C12—C15—H15A	109.5
H2A'—C2—H2B'	107.6	C12—C15—H15B	109.5
C2—C3—C4	112.8 (5)	H15A—C15—H15B	109.5
C2—C3—H3A	109.0	C12—C15—H15C	109.5
C4—C3—H3A	109.0	H15A—C15—H15C	109.5
C2—C3—H3B	109.0	H15B—C15—H15C	109.5
C4—C3—H3B	109.0	C12—C13'—H13D	109.5
H3A—C3—H3B	107.8	C12—C13'—H13E	109.5
N1—C4—C3	109.5 (4)	H13D—C13'—H13E	109.5
N1—C4—H4A	109.8	C12—C13'—H13F	109.5
C3—C4—H4A	109.8	H13D—C13'—H13F	109.5
N1—C4—H4B	109.8	H13E—C13'—H13F	109.5
C3—C4—H4B	109.8	C12—C14'—H14D	109.5
H4A—C4—H4B	108.2	C12—C14'—H14E	109.5
N1—C5—C6	127.7 (4)	H14D—C14'—H14E	109.5
N1—C5—H5	116.1	C12—C14'—H14F	109.5
C6—C5—H5	116.1	H14D—C14'—H14F	109.5
C7—C6—C11	119.2 (4)	H14E—C14'—H14F	109.5
C7—C6—C5	115.3 (4)	C12—C15'—H15D	109.5
C11—C6—C5	125.6 (4)	C12—C15'—H15E	109.5
C8—C7—C6	122.8 (4)	H15D—C15'—H15E	109.5
C8—C7—H7	118.6	C12—C15'—H15F	109.5
C6—C7—H7	118.6	H15D—C15'—H15F	109.5
C7—C8—C9	117.2 (3)	H15E—C15'—H15F	109.5
C7—C8—C12	121.5 (5)	O5—Cl1—O3	112.1 (6)
C9—C8—C12	121.3 (5)	O5—Cl1—O6	111.6 (6)
C8—C9—C10	122.6 (4)	O3—Cl1—O6	108.8 (7)
C8—C9—H9	118.7	O6'—Cl1—O3'	111.6 (6)
C10—C9—H9	118.7	O6'—Cl1—O5'	108.9 (7)
C11—C10—C9	120.2 (4)	O3'—Cl1—O5'	110.5 (6)
C11—C10—C1i	124.9 (4)	O6'—Cl1—O4'	109.0 (6)
C9—C10—C1i	114.9 (4)	O3'—Cl1—O4'	109.7 (6)
O1—C11—C10	121.7 (4)	O5'—Cl1—O4'	107.0 (7)
O1—C11—C6	120.2 (4)	O5—Cl1—O4	106.3 (6)
C10—C11—C6	118.0 (3)	O3—Cl1—O4	110.5 (6)
C15'—C12—C14'	108.7 (7)	O6—Cl1—O4	107.4 (6)
N1—Cu1—O1—C11	23.1 (3)	C5—C6—C7—C8	178.0 (5)
N2—Cu1—O1—C11	−141.7 (7)	C6—C7—C8—C9	2.3 (7)
O1i—Cu1—O1—C11	−169.4 (3)	C6—C7—C8—C12	179.9 (5)
N1—Cu1—O1—Cu1i	−174.27 (14)	C7—C8—C9—C10	−1.4 (7)
N2—Cu1—O1—Cu1i	21.0 (8)	C12—C8—C9—C10	−178.9 (5)
O1i—Cu1—O1—Cu1i	−6.78 (17)	C8—C9—C10—C11	−0.9 (8)
N2—Cu1—N1—C5	163.2 (4)	C8—C9—C10—C1i	178.9 (4)
O1i—Cu1—N1—C5	−61.8 (7)	Cu1i—O1—C11—C10	3.0 (5)
O1—Cu1—N1—C5	−13.7 (4)	Cu1—O1—C11—C10	161.7 (3)
N2—Cu1—N1—C4	−10.2 (4)	Cu1i—O1—C11—C6	−177.9 (3)
O1i—Cu1—N1—C4	124.9 (5)	Cu1—O1—C11—C6	−19.3 (5)
O1—Cu1—N1—C4	172.9 (3)	C9—C10—C11—O1	−178.7 (4)
N1—Cu1—N2—C1	173.9 (4)	C1i—C10—C11—O1	1.5 (7)
O1i—Cu1—N2—C1	5.4 (4)	C9—C10—C11—C6	2.3 (6)
O1—Cu1—N2—C1	−21.5 (10)	C1i—C10—C11—C6	−177.5 (5)
N1—Cu1—N2—C2	−7.4 (5)	C7—C6—C11—O1	179.5 (4)
O1i—Cu1—N2—C2	−175.8 (5)	C5—C6—C11—O1	0.7 (7)
O1—Cu1—N2—C2	157.3 (7)	C7—C6—C11—C10	−1.4 (7)
C2—N2—C1—C10i	178.0 (5)	C5—C6—C11—C10	179.8 (5)
Cu1—N2—C1—C10i	−3.2 (7)	C7—C8—C12—C15'	−172.3 (8)
C1—N2—C2—C3	163.5 (5)	C9—C8—C12—C15'	5.1 (9)
Cu1—N2—C2—C3	−15.3 (8)	C7—C8—C12—C14'	64.5 (9)
N2—C2—C3—C4	59.5 (7)	C9—C8—C12—C14'	−118.0 (8)
C5—N1—C4—C3	−125.1 (4)	C7—C8—C12—C13	7.0 (8)
Cu1—N1—C4—C3	48.7 (5)	C9—C8—C12—C13	−175.5 (6)
C2—C3—C4—N1	−77.9 (6)	C7—C8—C12—C14	127.7 (7)
C4—N1—C5—C6	175.2 (5)	C9—C8—C12—C14	−54.8 (7)
Cu1—N1—C5—C6	1.6 (7)	C7—C8—C12—C15	−116.1 (7)
N1—C5—C6—C7	−169.8 (5)	C9—C8—C12—C15	61.4 (8)
N1—C5—C6—C11	9.0 (9)	C7—C8—C12—C13'	−52.6 (9)
C11—C6—C7—C8	−0.9 (8)	C9—C8—C12—C13'	124.9 (8)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2B···O2ii	0.82 (2)	2.07 (4)	2.821 (6)	153 (8)
O2—H2A···O3	0.81 (2)	2.26 (3)	2.806 (8)	125 (2)
O2—H2A···O3′	0.81 (2)	2.49 (4)	2.947 (10)	117 (3)
O2—H2A···N1	0.81 (2)	2.55 (3)	3.197 (6)	138 (3)

Table 1

Selected bond lengths (Å)

Cu1—N1	1.939 (4)
Cu1—N2	1.945 (4)
Cu1—O1i	1.954 (3)
Cu1—O1	1.964 (3)
Cu1—O2	2.707 (5)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2B⋯O2ii	0.82 (2)	2.07 (4)	2.821 (6)	153 (8)
O2—H2A⋯O3	0.81 (2)	2.26 (3)	2.806 (8)	125 (2)
O2—H2A⋯O3′	0.81 (2)	2.49 (4)	2.947 (10)	117 (3)
O2—H2A⋯N1	0.81 (2)	2.55 (3)	3.197 (6)	138 (3)

Symmetry code: (ii) .