Diaqua-bis(ethyl-enediamine-κN,N')copper(II) bis-(4-phenyl-benzoate) 2.66-hydrate.

In the title complex, [Cu(C(2)H(8)N(2))(2)(H(2)O)(2)](C(13)H(9)O(2))(2)·2.66H(2)O, the Cu(II) centre (located at an inversion centre) is coordinated by two bidentate ethyl-enediamine (en) ligands and two water O atoms in a typical Jahn-Teller distorted octahedral geometry. The amino groups and the water mol-ecules are disordered over two distinct crystallographic positions with occupancies of 1/3 and 2/3. In the crystal, the cations and anions are disposed in alternating layers. One of the water mol-ecules of crystallization is disordered and the other has a fractional occupation. In the 2/3 occupancy component, water mol-ecules are organized into a chain composed of hexa-meric units inter-connected by carboxyl-ate bridges.

Related literature

For general background to reactions based on the copper cation, see: Graham et al. (2000 ▶); Majumder et al. (2006 ▶); Rao et al. (2004 ▶); Zhao et al. (2009 ▶). For examples of framework-type structures of hybrid materials comprising carboxyl­ate anions, see: Eddaoudi et al. (2001 ▶). For general background to crystal engineering approaches from our research group, see: Paz & Khimyak et al. (2002 ▶); Paz & Bond et al. (2002 ▶); Paz & Klinowski (2003 ▶); Paz et al. (2005 ▶); Shi et al. (2008 ▶). For a description of the graph-set notation for hydrogen-bonded aggregates, see: Grell et al. (1999 ▶).

Experimental

Crystal data

[Cu(C2H8N2)2(H2O)2](C13H9O2)2·2.66H2O

M = 662.20

Monoclinic,

a = 6.1466 (6) Å

b = 34.984 (3) Å

c = 7.3101 (7) Å

β = 95.819 (4)°

V = 1563.8 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.76 mm−1

T = 150 K

0.13 × 0.10 × 0.06 mm

Data collection

Bruker X8 Kappa CCD APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ▶) T min = 0.908, T max = 0.956

26073 measured reflections

4736 independent reflections

3908 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.137

S = 1.10

4736 reflections

259 parameters

15 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.52 e Å−3

Δρmin = −0.66 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT-Plus (Bruker, 2005 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810016223/tk2668sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810016223/tk2668Isup2.hkl

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

[Cu(C2H8N2)2(H2O)2](C13H9O2)2·2.66H2O	F(000) = 699
Mr = 662.20	Dx = 1.406 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9591 reflections
a = 6.1466 (6) Å	θ = 3.3–30.5°
b = 34.984 (3) Å	µ = 0.76 mm−1
c = 7.3101 (7) Å	T = 150 K
β = 95.819 (4)°	Needle, violet
V = 1563.8 (3) Å3	0.13 × 0.10 × 0.06 mm
Z = 2

Bruker X8 Kappa CCD APEXII diffractometer	4736 independent reflections
Radiation source: fine-focus sealed tube	3908 reflections with I > 2σ(I)
graphite	Rint = 0.034
ω/φ scans	θmax = 30.5°, θmin = 3.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −8→8
Tmin = 0.908, Tmax = 0.956	k = −47→49
26073 measured reflections	l = −10→9

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ2(Fo2) + (0.0755P)2 + 0.5782P] where P = (Fo2 + 2Fc2)/3
4736 reflections	(Δ/σ)max < 0.001
259 parameters	Δρmax = 0.52 e Å−3
15 restraints	Δρmin = −0.66 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 > 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	0.5000	0.0000	0.0000	0.02840 (11)
N1	0.6260 (4)	0.04498 (6)	0.1479 (3)	0.0285 (4)	0.67
H1A	0.5747	0.0453	0.2618	0.034*	0.67
H1B	0.7761	0.0434	0.1639	0.034*	0.67
N2	0.3249 (4)	0.03936 (6)	−0.1506 (3)	0.0326 (5)	0.67
H2A	0.3829	0.0428	−0.2607	0.039*	0.67
H2B	0.1831	0.0310	−0.1755	0.039*	0.67
C1	0.5555 (4)	0.08119 (5)	0.0418 (3)	0.0337 (4)	0.67
H1C	0.5564	0.1032	0.1272	0.040*	0.67
H1D	0.6583	0.0867	−0.0506	0.040*	0.67
C2	0.3274 (3)	0.07512 (5)	−0.0527 (3)	0.0336 (4)	0.67
H2C	0.2201	0.0744	0.0395	0.040*	0.67
H2D	0.2878	0.0963	−0.1393	0.040*	0.67
N1'	0.6818 (6)	0.04865 (12)	0.0030 (6)	0.0247 (8)	0.33
H1E	0.7995	0.0465	0.0907	0.030*	0.33
H1F	0.7345	0.0518	−0.1095	0.030*	0.33
N2'	0.2445 (6)	0.03581 (11)	−0.0017 (6)	0.0237 (8)	0.33
H2E	0.1326	0.0280	−0.0866	0.028*	0.33
H2F	0.1935	0.0365	0.1123	0.028*	0.33
C1'	0.5555 (4)	0.08119 (5)	0.0418 (3)	0.0337 (4)	0.33
H1G	0.6207	0.1047	−0.0051	0.040*	0.33
H1H	0.5507	0.0839	0.1762	0.040*	0.33
C2'	0.3274 (3)	0.07512 (5)	−0.0527 (3)	0.0336 (4)	0.33
H2G	0.3299	0.0769	−0.1876	0.040*	0.33
H2H	0.2282	0.0952	−0.0139	0.040*	0.33
O1W	0.4441 (9)	−0.00131 (10)	−0.3429 (6)	0.0369 (10)	0.33
H1M	0.467 (14)	0.0206 (7)	−0.415 (6)	0.055*	0.33
H1N	0.473 (14)	−0.0236 (7)	−0.410 (7)	0.055*	0.33
O1	0.3256 (2)	0.42163 (4)	0.1362 (2)	0.0358 (3)
O2	−0.0141 (2)	0.42725 (4)	0.00400 (19)	0.0357 (3)
C3	0.1443 (3)	0.40764 (5)	0.0747 (2)	0.0281 (3)
C4	0.1163 (3)	0.36494 (5)	0.0880 (2)	0.0246 (3)
C5	0.2925 (3)	0.34223 (5)	0.1570 (2)	0.0279 (3)
H5	0.4286	0.3538	0.1973	0.034*
C6	0.2705 (3)	0.30293 (5)	0.1670 (2)	0.0281 (3)
H6	0.3920	0.2879	0.2144	0.034*
C7	0.0717 (3)	0.28509 (4)	0.1083 (2)	0.0236 (3)
C8	−0.1055 (3)	0.30806 (5)	0.0421 (2)	0.0265 (3)
H8	−0.2425	0.2965	0.0035	0.032*
C9	−0.0835 (3)	0.34750 (5)	0.0321 (2)	0.0272 (3)
H9	−0.2052	0.3627	−0.0132	0.033*
C10	0.0507 (3)	0.24284 (4)	0.1143 (2)	0.0245 (3)
C11	0.2192 (3)	0.21931 (5)	0.0648 (3)	0.0288 (3)
H11	0.3483	0.2304	0.0270	0.035*
C12	0.1993 (3)	0.17987 (5)	0.0705 (3)	0.0343 (4)
H12	0.3136	0.1642	0.0343	0.041*
C13	0.0136 (3)	0.16311 (5)	0.1287 (3)	0.0353 (4)
H13	0.0019	0.1361	0.1346	0.042*
C14	−0.1549 (3)	0.18613 (5)	0.1784 (3)	0.0325 (4)
H14	−0.2825	0.1748	0.2182	0.039*
C15	−0.1371 (3)	0.22569 (5)	0.1697 (2)	0.0283 (3)
H15	−0.2541	0.2412	0.2019	0.034*
O2W	0.5759 (3)	0.43249 (6)	0.8469 (2)	0.0544 (5)
H2M	0.716 (3)	0.4273 (15)	0.908 (4)	0.082*	0.67
H2N	0.474 (4)	0.4355 (17)	0.935 (3)	0.082*	0.67
H2O	0.563 (15)	0.4550 (11)	0.918 (8)	0.082*	0.33
H2P	0.510 (14)	0.4117 (13)	0.904 (9)	0.082*	0.33
O3W	0.1809 (3)	−0.00801 (6)	0.2058 (3)	0.0345 (4)	0.67
H3M	0.124 (6)	0.0139 (5)	0.261 (4)	0.052*	0.67
H3N	0.184 (6)	−0.0289 (5)	0.289 (3)	0.052*	0.67
O4W	0.0081 (8)	0.99783 (6)	0.3679 (12)	0.067 (2)	0.33
H4M	0.0656	0.9728	0.3644	0.101*	0.33
H4N	0.1242 (18)	1.01587 (19)	0.377 (17)	0.101*	0.33

	U11	U22	U33	U12	U13	U23
Cu1	0.03755 (18)	0.01744 (15)	0.02768 (18)	0.00265 (10)	−0.00905 (12)	−0.00195 (10)
N1	0.0365 (11)	0.0218 (9)	0.0259 (10)	−0.0002 (8)	−0.0038 (8)	−0.0054 (8)
N2	0.0453 (13)	0.0211 (10)	0.0288 (11)	0.0044 (9)	−0.0085 (9)	−0.0006 (8)
C1	0.0507 (10)	0.0214 (8)	0.0297 (8)	−0.0054 (7)	0.0080 (7)	−0.0036 (6)
C2	0.0462 (10)	0.0230 (8)	0.0325 (9)	0.0091 (7)	0.0081 (8)	0.0035 (7)
N1'	0.0226 (17)	0.027 (2)	0.0234 (19)	−0.0036 (14)	−0.0015 (14)	0.0001 (15)
N2'	0.0203 (17)	0.0252 (18)	0.0253 (19)	−0.0006 (14)	0.0018 (14)	−0.0003 (15)
C1'	0.0507 (10)	0.0214 (8)	0.0297 (8)	−0.0054 (7)	0.0080 (7)	−0.0036 (6)
C2'	0.0462 (10)	0.0230 (8)	0.0325 (9)	0.0091 (7)	0.0081 (8)	0.0035 (7)
O1W	0.065 (3)	0.0230 (18)	0.0216 (18)	−0.0027 (16)	−0.0006 (18)	0.0007 (13)
O1	0.0410 (7)	0.0305 (6)	0.0368 (7)	−0.0123 (5)	0.0081 (6)	−0.0007 (5)
O2	0.0386 (7)	0.0244 (6)	0.0462 (9)	0.0002 (5)	0.0140 (6)	0.0015 (5)
C3	0.0374 (8)	0.0246 (7)	0.0247 (8)	−0.0056 (6)	0.0143 (6)	−0.0024 (6)
C4	0.0303 (7)	0.0227 (7)	0.0219 (7)	−0.0030 (6)	0.0076 (6)	−0.0022 (6)
C5	0.0277 (7)	0.0292 (8)	0.0267 (8)	−0.0051 (6)	0.0015 (6)	−0.0020 (6)
C6	0.0259 (7)	0.0298 (8)	0.0277 (8)	0.0004 (6)	−0.0014 (6)	−0.0001 (6)
C7	0.0263 (7)	0.0232 (7)	0.0211 (7)	−0.0008 (5)	0.0020 (5)	−0.0001 (6)
C8	0.0256 (7)	0.0236 (7)	0.0297 (8)	−0.0031 (6)	0.0004 (6)	0.0004 (6)
C9	0.0278 (7)	0.0245 (7)	0.0293 (8)	0.0001 (6)	0.0036 (6)	0.0009 (6)
C10	0.0291 (7)	0.0233 (7)	0.0203 (7)	−0.0007 (5)	−0.0016 (5)	0.0013 (5)
C11	0.0287 (7)	0.0263 (8)	0.0307 (8)	0.0026 (6)	−0.0006 (6)	0.0022 (6)
C12	0.0352 (9)	0.0266 (8)	0.0392 (10)	0.0074 (6)	−0.0048 (7)	−0.0010 (7)
C13	0.0442 (10)	0.0226 (8)	0.0368 (10)	−0.0002 (7)	−0.0076 (8)	0.0028 (7)
C14	0.0390 (9)	0.0274 (8)	0.0304 (9)	−0.0064 (7)	0.0002 (7)	0.0028 (7)
C15	0.0319 (8)	0.0268 (8)	0.0260 (8)	−0.0016 (6)	0.0028 (6)	−0.0008 (6)
O2W	0.0487 (9)	0.0846 (13)	0.0313 (8)	−0.0280 (9)	0.0115 (6)	−0.0046 (8)
O3W	0.0367 (10)	0.0221 (8)	0.0430 (12)	0.0042 (7)	−0.0037 (9)	−0.0011 (8)
O4W	0.040 (3)	0.028 (2)	0.129 (7)	−0.0058 (17)	−0.009 (3)	0.004 (3)

Cu1—N1	2.019 (2)	C3—C4	1.508 (2)
Cu1—N1'	2.035 (4)	C4—C9	1.395 (2)
Cu1—N2	2.006 (2)	C4—C5	1.395 (2)
Cu1—N2'	2.008 (4)	C5—C6	1.384 (2)
Cu1—O1W	2.496 (4)	C5—H5	0.9500
Cu1—O3W	2.605 (2)	C6—C7	1.400 (2)
Cu1—N2i	2.006 (2)	C6—H6	0.9500
Cu1—N2'i	2.008 (4)	C7—C8	1.400 (2)
Cu1—N1i	2.019 (2)	C7—C10	1.485 (2)
Cu1—N1'i	2.035 (4)	C8—C9	1.389 (2)
Cu1—O1Wi	2.496 (4)	C8—H8	0.9500
Cu1—O3Wi	2.605 (2)	C9—H9	0.9500
N1—C1	1.525 (3)	C10—C15	1.397 (2)
N1—H1A	0.9200	C10—C11	1.399 (2)
N1—H1B	0.9200	C11—C12	1.386 (2)
N2—C2	1.441 (3)	C11—H11	0.9500
N2—H2A	0.9200	C12—C13	1.388 (3)
N2—H2B	0.9200	C12—H12	0.9500
C1—C2	1.514 (3)	C13—C14	1.389 (3)
C1—H1C	0.9900	C13—H13	0.9500
C1—H1D	0.9900	C14—C15	1.390 (2)
C2—H2C	0.9900	C14—H14	0.9500
C2—H2D	0.9900	C15—H15	0.9500
N1'—H1E	0.9200	O2W—H2M	0.9500 (11)
N1'—H1F	0.9200	O2W—H2N	0.9500 (10)
N2'—H2E	0.9200	O2W—H2O	0.9500 (11)
N2'—H2F	0.9200	O2W—H2P	0.9500 (12)
O1W—H1M	0.9500 (10)	O3W—H3M	0.9499 (10)
O1W—H1N	0.9500 (10)	O3W—H3N	0.9500 (10)
O1—C3	1.258 (2)	O4W—H4M	0.9457
O2—C3	1.258 (2)	O4W—H4N	0.950 (2)
N2—Cu1—N1	85.08 (9)	H2A—N2—H2B	108.1
N2—Cu1—N1i	94.92 (9)	C2—C1—N1	108.52 (15)
N2'—Cu1—N1'	84.65 (15)	C2—C1—Cu1	73.63 (9)
N2'—Cu1—N1'i	95.35 (15)	C2—C1—H1C	110.0
N1'—Cu1—O1W	92.62 (15)	N1—C1—H1C	110.0
N1'—Cu1—O1Wi	87.38 (15)	Cu1—C1—H1C	145.9
N2i—Cu1—N2	180.00 (9)	C2—C1—H1D	110.0
N2i—Cu1—N2'i	36.18 (14)	N1—C1—H1D	110.0
N2—Cu1—N2'i	143.82 (14)	Cu1—C1—H1D	101.4
N2i—Cu1—N2'	143.82 (14)	H1C—C1—H1D	108.4
N2—Cu1—N2'	36.18 (14)	N2—C2—C1	108.13 (16)
N2'i—Cu1—N2'	180.0 (3)	C1—C2—Cu1	75.67 (9)
N2i—Cu1—N1i	85.08 (9)	N2—C2—H2C	110.1
N2'i—Cu1—N1i	76.97 (13)	C1—C2—H2C	110.1
N2'—Cu1—N1i	103.03 (13)	Cu1—C2—H2C	98.7
N2i—Cu1—N1	94.92 (9)	N2—C2—H2D	110.1
N2'i—Cu1—N1	103.03 (13)	C1—C2—H2D	110.1
N2'—Cu1—N1	76.97 (13)	Cu1—C2—H2D	147.5
N1i—Cu1—N1	180.00 (14)	H2C—C2—H2D	108.4
N2i—Cu1—N1'i	72.26 (13)	Cu1—N1'—H1E	109.4
N2—Cu1—N1'i	107.74 (13)	Cu1—N1'—H1F	109.4
N2'i—Cu1—N1'i	84.65 (15)	H1E—N1'—H1F	108.0
N1i—Cu1—N1'i	33.06 (14)	Cu1—N2'—H2E	110.4
N1—Cu1—N1'i	146.94 (14)	Cu1—N2'—H2F	110.4
N2i—Cu1—N1'	107.74 (13)	H2E—N2'—H2F	108.6
N2—Cu1—N1'	72.26 (13)	Cu1—O1W—H1M	122 (3)
N2'i—Cu1—N1'	95.35 (15)	Cu1—O1W—H1N	121 (4)
N1i—Cu1—N1'	146.94 (14)	H1M—O1W—H1N	109.34 (16)
N1—Cu1—N1'	33.06 (14)	O2—C3—O1	123.74 (16)
N1'i—Cu1—N1'	180.00 (13)	O2—C3—C4	118.56 (15)
N2i—Cu1—O1Wi	56.63 (12)	O1—C3—C4	117.70 (16)
N2—Cu1—O1Wi	123.37 (12)	C9—C4—C5	119.00 (15)
N2'i—Cu1—O1Wi	88.69 (17)	C9—C4—C3	121.13 (15)
N2'—Cu1—O1Wi	91.31 (17)	C5—C4—C3	119.86 (15)
N1i—Cu1—O1Wi	123.96 (11)	C6—C5—C4	120.56 (15)
N1—Cu1—O1Wi	56.04 (11)	C6—C5—H5	119.7
N1'i—Cu1—O1Wi	92.62 (15)	C4—C5—H5	119.7
N2i—Cu1—O1W	123.37 (12)	C5—C6—C7	120.87 (15)
N2—Cu1—O1W	56.63 (12)	C5—C6—H6	119.6
N2'i—Cu1—O1W	91.31 (17)	C7—C6—H6	119.6
N2'—Cu1—O1W	88.69 (17)	C8—C7—C6	118.33 (15)
N1i—Cu1—O1W	56.04 (11)	C8—C7—C10	120.99 (14)
N1—Cu1—O1W	123.96 (11)	C6—C7—C10	120.68 (14)
N1'i—Cu1—O1W	87.38 (15)	C9—C8—C7	120.77 (15)
O1Wi—Cu1—O1W	180.0	C9—C8—H8	119.6
N2i—Cu1—O3W	90.15 (9)	C7—C8—H8	119.6
N2—Cu1—O3W	89.85 (9)	C8—C9—C4	120.45 (15)
N2'i—Cu1—O3W	124.30 (13)	C8—C9—H9	119.8
N2'—Cu1—O3W	55.70 (13)	C4—C9—H9	119.8
N1i—Cu1—O3W	87.42 (8)	C15—C10—C11	118.51 (15)
N1—Cu1—O3W	92.58 (8)	C15—C10—C7	120.86 (15)
N1'i—Cu1—O3W	58.09 (13)	C11—C10—C7	120.64 (15)
N1'—Cu1—O3W	121.91 (13)	C12—C11—C10	120.55 (17)
O1Wi—Cu1—O3W	57.13 (13)	C12—C11—H11	119.7
O1W—Cu1—O3W	122.87 (13)	C10—C11—H11	119.7
N2i—Cu1—O3Wi	89.85 (9)	C11—C12—C13	120.49 (17)
N2—Cu1—O3Wi	90.15 (9)	C11—C12—H12	119.8
N2'i—Cu1—O3Wi	55.70 (13)	C13—C12—H12	119.8
N2'—Cu1—O3Wi	124.30 (13)	C12—C13—C14	119.58 (16)
N1i—Cu1—O3Wi	92.58 (8)	C12—C13—H13	120.2
N1—Cu1—O3Wi	87.42 (8)	C14—C13—H13	120.2
N1'i—Cu1—O3Wi	121.91 (13)	C13—C14—C15	120.06 (17)
N1'—Cu1—O3Wi	58.09 (13)	C13—C14—H14	120.0
O1Wi—Cu1—O3Wi	122.87 (13)	C15—C14—H14	120.0
O1W—Cu1—O3Wi	57.13 (13)	C14—C15—C10	120.80 (16)
O3W—Cu1—O3Wi	180.00 (5)	C14—C15—H15	119.6
C1—N1—Cu1	107.53 (14)	C10—C15—H15	119.6
C1—N1—H1A	110.2	H2M—O2W—H2N	109.33 (16)
Cu1—N1—H1A	110.2	H2M—O2W—H2O	91 (6)
C1—N1—H1B	110.2	H2N—O2W—H2O	56 (4)
Cu1—N1—H1B	110.2	H2M—O2W—H2P	93 (6)
H1A—N1—H1B	108.5	H2N—O2W—H2P	56 (4)
C2—N2—Cu1	110.19 (15)	H2O—O2W—H2P	109.33 (17)
C2—N2—H2A	109.6	Cu1—O3W—H3M	119 (2)
Cu1—N2—H2A	109.6	Cu1—O3W—H3N	119 (2)
C2—N2—H2B	109.6	H3M—O3W—H3N	109.33 (16)
Cu1—N2—H2B	109.6	H4M—O4W—H4N	109.7
N2i—Cu1—N1—C1	168.87 (15)	N2'i—Cu1—C2—N2	102.4 (3)
N2—Cu1—N1—C1	−11.13 (15)	N2'—Cu1—C2—N2	−77.6 (3)
N2'i—Cu1—N1—C1	133.12 (18)	N1i—Cu1—C2—N2	−19.2 (2)
N2'—Cu1—N1—C1	−46.88 (18)	N1—Cu1—C2—N2	160.8 (2)
N1'i—Cu1—N1—C1	−126.5 (2)	N1'i—Cu1—C2—N2	−59.0 (2)
N1'—Cu1—N1—C1	53.5 (2)	N1'—Cu1—C2—N2	121.0 (2)
O1Wi—Cu1—N1—C1	−147.5 (2)	O1Wi—Cu1—C2—N2	−157.5 (2)
O1W—Cu1—N1—C1	32.5 (2)	O1W—Cu1—C2—N2	22.5 (2)
O3W—Cu1—N1—C1	−100.76 (15)	O3W—Cu1—C2—N2	−102.02 (19)
O3Wi—Cu1—N1—C1	79.24 (15)	O3Wi—Cu1—C2—N2	77.98 (19)
N2'i—Cu1—N2—C2	−121.7 (2)	N2i—Cu1—C2—C1	39.2 (2)
N2'—Cu1—N2—C2	58.3 (2)	N2—Cu1—C2—C1	−140.8 (2)
N1i—Cu1—N2—C2	163.71 (18)	N2'i—Cu1—C2—C1	−38.4 (3)
N1—Cu1—N2—C2	−16.29 (18)	N2'—Cu1—C2—C1	141.6 (3)
N1'i—Cu1—N2—C2	132.5 (2)	N1i—Cu1—C2—C1	−160.01 (12)
N1'—Cu1—N2—C2	−47.5 (2)	N1—Cu1—C2—C1	19.99 (12)
O1Wi—Cu1—N2—C2	27.0 (3)	N1'i—Cu1—C2—C1	160.24 (18)
O1W—Cu1—N2—C2	−153.0 (3)	N1'—Cu1—C2—C1	−19.76 (18)
O3W—Cu1—N2—C2	76.31 (18)	O1Wi—Cu1—C2—C1	61.70 (16)
O3Wi—Cu1—N2—C2	−103.69 (18)	O1W—Cu1—C2—C1	−118.30 (16)
Cu1—N1—C1—C2	35.43 (19)	O3W—Cu1—C2—C1	117.21 (12)
N2i—Cu1—C1—C2	−158.57 (13)	O3Wi—Cu1—C2—C1	−62.79 (12)
N2—Cu1—C1—C2	21.43 (13)	O2—C3—C4—C9	−3.1 (2)
N2'i—Cu1—C1—C2	157.87 (17)	O1—C3—C4—C9	176.50 (16)
N2'—Cu1—C1—C2	−22.13 (17)	O2—C3—C4—C5	176.68 (16)
N1i—Cu1—C1—C2	35.0 (2)	O1—C3—C4—C5	−3.7 (2)
N1—Cu1—C1—C2	−145.0 (2)	C9—C4—C5—C6	1.0 (3)
N1'i—Cu1—C1—C2	−36.8 (3)	C3—C4—C5—C6	−178.83 (15)
N1'—Cu1—C1—C2	143.2 (3)	C4—C5—C6—C7	0.0 (3)
O1Wi—Cu1—C1—C2	−118.33 (16)	C5—C6—C7—C8	−1.1 (3)
O1W—Cu1—C1—C2	61.67 (16)	C5—C6—C7—C10	178.21 (16)
O3W—Cu1—C1—C2	−63.05 (12)	C6—C7—C8—C9	1.0 (3)
O3Wi—Cu1—C1—C2	116.95 (12)	C10—C7—C8—C9	−178.23 (16)
N2i—Cu1—C1—N1	−13.52 (19)	C7—C8—C9—C4	0.0 (3)
N2—Cu1—C1—N1	166.48 (19)	C5—C4—C9—C8	−1.0 (3)
N2'i—Cu1—C1—N1	−57.1 (2)	C3—C4—C9—C8	178.81 (16)
N2'—Cu1—C1—N1	122.9 (2)	C8—C7—C10—C15	−41.2 (2)
N1i—Cu1—C1—N1	180.0	C6—C7—C10—C15	139.60 (17)
N1'i—Cu1—C1—N1	108.2 (3)	C8—C7—C10—C11	138.95 (17)
N1'—Cu1—C1—N1	−71.8 (3)	C6—C7—C10—C11	−40.3 (2)
O1Wi—Cu1—C1—N1	26.7 (2)	C15—C10—C11—C12	0.1 (2)
O1W—Cu1—C1—N1	−153.3 (2)	C7—C10—C11—C12	−179.99 (16)
O3W—Cu1—C1—N1	81.99 (16)	C10—C11—C12—C13	−1.2 (3)
O3Wi—Cu1—C1—N1	−98.01 (16)	C11—C12—C13—C14	1.2 (3)
Cu1—N2—C2—C1	40.1 (2)	C12—C13—C14—C15	0.0 (3)
N1—C1—C2—N2	−50.0 (2)	C13—C14—C15—C10	−1.1 (3)
Cu1—C1—C2—N2	−26.13 (15)	C11—C10—C15—C14	1.0 (2)
N1—C1—C2—Cu1	−23.88 (13)	C7—C10—C15—C14	−178.88 (16)
N2i—Cu1—C2—N2	180.0

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2ii	0.92	2.13	2.986 (3)	154
N1—H1B···O2Wiii	0.92	2.32	3.093 (3)	141
N2—H2A···O2iii	0.92	2.16	3.037 (3)	158
N1'—H1E···O2Wiii	0.92	2.51	3.375 (4)	157
N1'—H1F···O1iii	0.92	2.20	3.087 (5)	161
N2'—H2E···O4Wiv	0.92	2.33	3.181 (9)	154
N2'—H2F···O2Wv	0.92	2.21	3.055 (5)	152
O1W—H1M···O2iii	0.95 (1)	1.92 (1)	2.844 (4)	163 (4)
O1W—H1N···O2vi	0.95 (1)	1.88 (1)	2.814 (4)	169 (4)
O2W—H2M···O2vii	0.95 (1)	1.73 (1)	2.668 (2)	168 (5)
O2W—H2N···O1viii	0.95 (1)	1.87 (2)	2.765 (2)	156 (5)
O3W—H3M···O2Wv	0.95 (1)	2.01 (1)	2.932 (3)	163 (3)
O3W—H3N···O1ix	0.95 (1)	1.82 (1)	2.721 (3)	158 (3)
O4W—H4M···O1x	0.95 (1)	1.91	2.8562 (17)	178

Table 1

Selected bond lengths (Å)

Cu1—N1	2.019 (2)
Cu1—N1′	2.035 (4)
Cu1—N2	2.006 (2)
Cu1—N2′	2.008 (4)
Cu1—O1W	2.496 (4)
Cu1—O3W	2.605 (2)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2ii	0.92	2.13	2.986 (3)	154
N1—H1B⋯O2Wiii	0.92	2.32	3.093 (3)	141
N2—H2A⋯O2iii	0.92	2.16	3.037 (3)	158
N1′—H1E⋯O2Wiii	0.92	2.51	3.375 (4)	157
N1′—H1F⋯O1iii	0.92	2.20	3.087 (5)	161
N2′—H2E⋯O4Wiv	0.92	2.33	3.181 (9)	154
N2′—H2F⋯O2Wv	0.92	2.21	3.055 (5)	152
O1W—H1M⋯O2iii	0.95 (1)	1.92 (1)	2.844 (4)	163 (4)
O1W—H1N⋯O2vi	0.95 (1)	1.88 (1)	2.814 (4)	169 (4)
O2W—H2M⋯O2vii	0.95 (1)	1.73 (1)	2.668 (2)	168 (5)
O2W—H2N⋯O1viii	0.95 (1)	1.87 (2)	2.765 (2)	156 (5)
O3W—H3M⋯O2Wv	0.95 (1)	2.01 (1)	2.932 (3)	163 (3)
O3W—H3N⋯O1ix	0.95 (1)	1.82 (1)	2.721 (3)	158 (3)
O4W—H4M⋯O1x	0.95 (1)	1.91	2.8562 (17)	178

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