Bis(1,10-phenanthroline-κN,N')(sulfato-O)copper(II) ethane-1,2-diol monosolvate.

In the title compound, [Cu(SO(4))(C(12)H(8)N(2))(2)]·C(2)H(6)O(2), the Cu(II) ion is five-coordinated in a distorted square-pyramidal manner by four N atoms from two chelating 1,10-phenanthroline (phen) ligands and one O atom from a monodentate sulfate anion. The four N atoms comprise a square and the one O atom the apex of a square pyramid. The two chelating N(2)C(2) groups are oriented at 71.1 (2)°. In the crystal, the components are connected by inter-molecular O-H⋯O hydrogen bonding. The presence of pseudosymmetry in the structure suggests the higher symmetry space group C2/c, but attempts to refine the structure in this space group resulted in an unsatisfactory model.

Related literature

For the propane-1,2-diol solvate of the title complex, see: Zhong (2011 ▶). For related structures of transition n class="Chemical">metal complexes of phen and for background references, see: Zhong et al. (2006 ▶; 2009 ▶); Zhong & Cui (2010 ▶); Ni et al. (2010 ▶); Zhong (2010 ▶); Cui et al. (2010 ▶).

Experimental

Crystal data

[Cu(SO4)(C12n class="Species">H8N2)2]·C2H6O2

M = 582.08

Monoclinic,

a = 17.666 (4) Å

b = 11.992 (2) Å

c = 13.122 (3) Å

β = 120.96 (3)°

V = 2383.8 (11) Å3

Z = 4

Mo Kα radiation

μ = 1.06 mm−1

T = 223 K

0.40 × 0.35 × 0.25 mm

Data collection

Rigaku Mercury CCD diffractometer

Absorption correction: multi-scan (REQAB; Jacobson, 1998 ▶) T min = 0.776, T max = 1.000

6663 measured reflections

4089 independent reflections

3835 reflections with I > 2/s(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.102

S = 1.06

4089 reflections

344 parameters

2 restraints

H-atom parameters constrained

Δρmax = 1.07 e Å−3

Δρmin = −0.81 e Å−3

Absolute structure: Flack (1983 ▶), 1396 Friedel pairs

Flack parameter: 0.254 (14)

Data collection: CrystalClear (Rigaku, 2007 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811031175/bt5595sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811031175/bt5595Isup2.hkl

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

[Cu(SO4)(C12H8N2)2]·C2H6O2	F(000) = 1196
Mr = 582.08	Dx = 1.622 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 5713 reflections
a = 17.666 (4) Å	θ = 3.2–27.5°
b = 11.992 (2) Å	µ = 1.06 mm−1
c = 13.122 (3) Å	T = 223 K
β = 120.96 (3)°	Block, green
V = 2383.8 (11) Å3	0.40 × 0.35 × 0.25 mm
Z = 4

Rigaku Mercury CCD diffractometer	4089 independent reflections
Radiation source: fine-focus sealed tube	3835 reflections with I > 2/s(I)
Graphite Monochromator	Rint = 0.018
Detector resolution: 28.5714 pixels mm-1	θmax = 27.5°, θmin = 3.2°
ω scans	h = −21→22
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	k = −13→15
Tmin = 0.776, Tmax = 1.000	l = −15→17
6663 measured reflections

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-atom parameters constrained
wR(F2) = 0.102	w = 1/[σ2(Fo2) + (0.064P)2 + 1.9064P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
4089 reflections	Δρmax = 1.07 e Å−3
344 parameters	Δρmin = −0.81 e Å−3
2 restraints	Absolute structure: Flack (1983), 1396 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.254 (14)

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
Cu1	0.17114 (3)	0.28325 (3)	0.03203 (4)	0.02354 (12)
S1	0.16061 (6)	0.54366 (7)	0.04366 (9)	0.0262 (2)
N3	0.2587 (3)	0.2724 (3)	−0.0216 (4)	0.0220 (8)
N2	0.0827 (3)	0.2673 (3)	0.0820 (4)	0.0253 (8)
C24	0.3290 (3)	0.2059 (3)	0.0478 (4)	0.0215 (9)
N1	0.0735 (2)	0.1831 (3)	−0.1135 (3)	0.0246 (8)
N4	0.2650 (2)	0.1851 (3)	0.1690 (3)	0.0223 (7)
C11	0.0105 (3)	0.2038 (3)	0.0078 (4)	0.0235 (9)
C8	−0.0484 (3)	0.2248 (4)	0.1356 (5)	0.0298 (11)
H8A	−0.0915	0.2107	0.1546	0.036*
C15	0.3855 (4)	0.2311 (4)	−0.0817 (5)	0.0335 (11)
H15A	0.4279	0.2186	−0.1023	0.040*
O4	0.0858 (2)	0.6189 (3)	−0.0263 (3)	0.0336 (7)
C14	0.2517 (3)	0.3163 (4)	−0.1194 (4)	0.0268 (9)
H14A	0.2038	0.3622	−0.1669	0.032*
C10	0.0876 (3)	0.3084 (4)	0.1789 (5)	0.0313 (10)
H10A	0.1356	0.3532	0.2291	0.038*
C12	0.0056 (3)	0.1594 (4)	−0.0968 (4)	0.0218 (8)
C19	0.4077 (3)	0.0962 (3)	0.2325 (4)	0.0255 (10)
C4	−0.0682 (3)	0.0986 (4)	−0.1775 (4)	0.0264 (10)
O3	0.2432 (2)	0.5960 (3)	0.0654 (3)	0.0365 (8)
C13	0.3122 (4)	0.2966 (4)	−0.1525 (5)	0.0320 (11)
H13A	0.3042	0.3272	−0.2225	0.038*
C9	0.0224 (4)	0.2870 (3)	0.2096 (5)	0.0298 (11)
H9A	0.0287	0.3154	0.2795	0.036*
C18	0.4738 (3)	0.0761 (4)	0.2050 (5)	0.0302 (11)
H18A	0.5224	0.0334	0.2573	0.036*
C5	−0.1378 (3)	0.0776 (4)	−0.1545 (4)	0.0316 (11)
H5A	−0.1872	0.0370	−0.2087	0.038*
C7	−0.0582 (3)	0.1810 (4)	0.0300 (4)	0.0251 (9)
C16	0.3945 (3)	0.1835 (4)	0.0227 (4)	0.0260 (9)
C17	0.4695 (3)	0.1164 (4)	0.1054 (4)	0.0315 (10)
H17A	0.5145	0.1010	0.0904	0.038*
C3	−0.0707 (3)	0.0591 (4)	−0.2814 (4)	0.0310 (10)
H3A	−0.1183	0.0171	−0.3374	0.037*
C23	0.3340 (3)	0.1616 (4)	0.1529 (4)	0.0218 (8)
C6	−0.1316 (3)	0.1171 (4)	−0.0534 (4)	0.0318 (10)
H6A	−0.1766	0.1018	−0.0385	0.038*
C20	0.4089 (3)	0.0575 (4)	0.3340 (4)	0.0318 (10)
H20A	0.4558	0.0141	0.3892	0.038*
C2	−0.0025 (4)	0.0838 (4)	−0.2974 (5)	0.0350 (12)
H2A	−0.0038	0.0601	−0.3658	0.042*
C22	0.2710 (3)	0.1466 (4)	0.2686 (4)	0.0294 (10)
H22A	0.2257	0.1632	0.2826	0.035*
C21	0.3416 (4)	0.0832 (4)	0.3522 (4)	0.0348 (12)
H21A	0.3430	0.0584	0.4203	0.042*
C1	0.0701 (3)	0.1451 (4)	−0.2109 (4)	0.0300 (9)
H1A	0.1171	0.1593	−0.2220	0.036*
O1	0.1418 (2)	0.4369 (2)	−0.0255 (3)	0.0357 (7)
O6	0.1139 (3)	0.8222 (3)	0.0846 (4)	0.0541 (11)
H6B	0.1059	0.7631	0.0492	0.081*
O5	0.2232 (3)	0.8087 (3)	−0.0330 (4)	0.0503 (10)
H5B	0.2288	0.7496	0.0017	0.075*
C26	0.1316 (6)	0.9055 (4)	0.0264 (7)	0.058 (2)
H26A	0.1279	0.9770	0.0584	0.070*
H26B	0.0857	0.9042	−0.0569	0.070*
C25	0.2177 (4)	0.8984 (5)	0.0348 (6)	0.0586 (18)
H25A	0.2289	0.9681	0.0072	0.070*
H25B	0.2635	0.8890	0.1175	0.070*
O2	0.1672 (2)	0.5194 (2)	0.1578 (2)	0.0332 (6)

	U11	U22	U33	U12	U13	U23
Cu1	0.0233 (2)	0.0247 (2)	0.0272 (2)	0.0012 (2)	0.01621 (16)	0.0011 (3)
S1	0.0221 (5)	0.0222 (4)	0.0277 (5)	0.0012 (4)	0.0079 (4)	−0.0003 (4)
N3	0.022 (2)	0.0252 (19)	0.0229 (19)	0.0066 (14)	0.0142 (17)	0.0048 (15)
N2	0.025 (2)	0.0251 (19)	0.027 (2)	0.0026 (15)	0.0137 (19)	−0.0009 (16)
C24	0.024 (2)	0.021 (2)	0.019 (2)	0.0000 (16)	0.0106 (18)	−0.0046 (16)
N1	0.0242 (19)	0.0254 (19)	0.0228 (18)	−0.0047 (15)	0.0110 (16)	−0.0030 (15)
N4	0.0291 (19)	0.0201 (17)	0.0215 (17)	−0.0015 (15)	0.0158 (16)	−0.0010 (15)
C11	0.020 (2)	0.022 (2)	0.028 (2)	0.0029 (16)	0.012 (2)	0.0011 (18)
C8	0.027 (3)	0.033 (3)	0.038 (3)	−0.0001 (19)	0.023 (2)	0.005 (2)
C15	0.040 (3)	0.037 (3)	0.034 (3)	−0.003 (2)	0.026 (2)	−0.001 (2)
O4	0.0286 (16)	0.0358 (16)	0.0351 (16)	0.0043 (13)	0.0155 (14)	0.0010 (14)
C14	0.025 (2)	0.035 (2)	0.023 (2)	0.0033 (19)	0.015 (2)	0.005 (2)
C10	0.035 (3)	0.028 (2)	0.034 (3)	−0.002 (2)	0.019 (2)	−0.003 (2)
C12	0.024 (2)	0.0184 (18)	0.0227 (19)	0.0034 (17)	0.0119 (18)	0.0053 (17)
C19	0.025 (2)	0.018 (2)	0.023 (2)	−0.0011 (17)	0.0053 (19)	−0.0057 (18)
C4	0.024 (2)	0.028 (2)	0.025 (2)	0.0002 (18)	0.010 (2)	0.0010 (19)
O3	0.0219 (16)	0.0410 (19)	0.049 (2)	0.0042 (13)	0.0197 (15)	0.0121 (15)
C13	0.034 (3)	0.038 (3)	0.029 (3)	0.004 (2)	0.019 (2)	0.005 (2)
C9	0.037 (3)	0.031 (3)	0.033 (3)	0.0004 (19)	0.026 (2)	0.0018 (19)
C18	0.022 (2)	0.032 (3)	0.032 (2)	0.0006 (18)	0.010 (2)	−0.002 (2)
C5	0.025 (3)	0.028 (2)	0.030 (2)	−0.0058 (18)	0.005 (2)	−0.0016 (19)
C7	0.027 (2)	0.024 (2)	0.028 (2)	0.0057 (18)	0.016 (2)	0.0078 (19)
C16	0.020 (2)	0.027 (2)	0.031 (2)	−0.0002 (18)	0.013 (2)	−0.001 (2)
C17	0.023 (2)	0.032 (2)	0.035 (2)	−0.0005 (19)	0.012 (2)	−0.006 (2)
C3	0.033 (3)	0.029 (2)	0.025 (2)	−0.001 (2)	0.010 (2)	−0.004 (2)
C23	0.021 (2)	0.022 (2)	0.0214 (19)	0.0024 (17)	0.0105 (18)	0.0008 (17)
C6	0.025 (2)	0.037 (3)	0.038 (3)	−0.006 (2)	0.019 (2)	0.001 (2)
C20	0.031 (3)	0.030 (3)	0.025 (2)	0.006 (2)	0.007 (2)	0.002 (2)
C2	0.046 (3)	0.032 (3)	0.028 (2)	−0.007 (2)	0.020 (2)	−0.006 (2)
C22	0.033 (3)	0.035 (2)	0.027 (2)	0.008 (2)	0.021 (2)	0.006 (2)
C21	0.040 (3)	0.035 (3)	0.025 (2)	0.004 (2)	0.014 (2)	0.009 (2)
C1	0.035 (3)	0.030 (2)	0.026 (2)	−0.001 (2)	0.017 (2)	−0.002 (2)
O1	0.0474 (18)	0.0267 (13)	0.0325 (15)	0.0058 (13)	0.0201 (14)	−0.0012 (12)
O6	0.084 (3)	0.037 (2)	0.069 (3)	−0.003 (2)	0.059 (3)	−0.008 (2)
O5	0.068 (3)	0.047 (2)	0.057 (2)	−0.006 (2)	0.048 (2)	0.0026 (19)
C26	0.111 (6)	0.020 (2)	0.068 (4)	−0.002 (3)	0.065 (5)	−0.006 (3)
C25	0.053 (4)	0.059 (4)	0.058 (4)	−0.029 (3)	0.025 (3)	−0.014 (3)
O2	0.0381 (17)	0.0364 (15)	0.0265 (13)	−0.0035 (13)	0.0176 (13)	0.0002 (13)

Cu1—O1	1.957 (3)	C19—C18	1.409 (7)
Cu1—N2	1.990 (4)	C19—C23	1.415 (6)
Cu1—N3	2.006 (4)	C4—C3	1.422 (7)
Cu1—N4	2.073 (4)	C4—C5	1.432 (7)
Cu1—N1	2.162 (4)	C13—H13A	0.9300
S1—O4	1.469 (3)	C9—H9A	0.9300
S1—O2	1.470 (3)	C18—C17	1.358 (7)
S1—O3	1.475 (3)	C18—H18A	0.9300
S1—O1	1.504 (3)	C5—C6	1.359 (7)
N3—C14	1.333 (6)	C5—H5A	0.9300
N3—C24	1.358 (6)	C7—C6	1.416 (7)
N2—C10	1.324 (7)	C16—C17	1.451 (7)
N2—C11	1.371 (6)	C17—H17A	0.9300
C24—C16	1.382 (6)	C3—C2	1.358 (7)
C24—C23	1.437 (6)	C3—H3A	0.9300
N1—C1	1.330 (6)	C6—H6A	0.9300
N1—C12	1.354 (5)	C20—C21	1.363 (7)
N4—C22	1.338 (6)	C20—H20A	0.9300
N4—C23	1.369 (5)	C2—C1	1.406 (7)
C11—C7	1.412 (6)	C2—H2A	0.9300
C11—C12	1.433 (6)	C22—C21	1.389 (7)
C8—C9	1.347 (8)	C22—H22A	0.9300
C8—C7	1.408 (7)	C21—H21A	0.9300
C8—H8A	0.9300	C1—H1A	0.9300
C15—C13	1.386 (8)	O6—C26	1.386 (7)
C15—C16	1.415 (7)	O6—H6B	0.8200
C15—H15A	0.9300	O5—C25	1.430 (7)
C14—C13	1.365 (7)	O5—H5B	0.8200
C14—H14A	0.9300	C26—C25	1.472 (8)
C10—C9	1.426 (7)	C26—H26A	0.9700
C10—H10A	0.9300	C26—H26B	0.9700
C12—C4	1.390 (6)	C25—H25A	0.9700
C19—C20	1.401 (7)	C25—H25B	0.9700
O1—Cu1—N2	96.90 (14)	C8—C9—C10	118.8 (5)
O1—Cu1—N3	91.43 (13)	C8—C9—H9A	120.6
N2—Cu1—N3	170.72 (10)	C10—C9—H9A	120.6
O1—Cu1—N4	143.49 (13)	C17—C18—C19	122.8 (5)
N2—Cu1—N4	94.19 (15)	C17—C18—H18A	118.6
N3—Cu1—N4	81.39 (15)	C19—C18—H18A	118.6
O1—Cu1—N1	104.46 (13)	C6—C5—C4	119.8 (4)
N2—Cu1—N1	80.37 (15)	C6—C5—H5A	120.1
N3—Cu1—N1	93.63 (15)	C4—C5—H5A	120.1
N4—Cu1—N1	111.67 (10)	C8—C7—C11	116.6 (4)
O4—S1—O2	109.46 (18)	C8—C7—C6	124.2 (4)
O4—S1—O3	110.01 (16)	C11—C7—C6	119.2 (4)
O2—S1—O3	109.6 (2)	C24—C16—C15	117.5 (4)
O4—S1—O1	107.30 (19)	C24—C16—C17	119.0 (4)
O2—S1—O1	108.83 (17)	C15—C16—C17	123.5 (4)
O3—S1—O1	111.61 (19)	C18—C17—C16	119.6 (5)
C14—N3—C24	118.5 (4)	C18—C17—H17A	120.2
C14—N3—Cu1	127.3 (3)	C16—C17—H17A	120.2
C24—N3—Cu1	114.0 (3)	C2—C3—C4	118.9 (4)
C10—N2—C11	117.8 (4)	C2—C3—H3A	120.6
C10—N2—Cu1	127.3 (4)	C4—C3—H3A	120.6
C11—N2—Cu1	114.9 (3)	N4—C23—C19	123.7 (4)
N3—C24—C16	122.9 (4)	N4—C23—C24	116.9 (4)
N3—C24—C23	116.3 (4)	C19—C23—C24	119.4 (4)
C16—C24—C23	120.7 (4)	C5—C6—C7	121.7 (4)
C1—N1—C12	118.5 (4)	C5—C6—H6A	119.2
C1—N1—Cu1	131.3 (3)	C7—C6—H6A	119.2
C12—N1—Cu1	110.2 (3)	C21—C20—C19	120.3 (4)
C22—N4—C23	116.7 (4)	C21—C20—H20A	119.9
C22—N4—Cu1	132.0 (3)	C19—C20—H20A	119.9
C23—N4—Cu1	111.2 (3)	C3—C2—C1	120.1 (5)
N2—C11—C7	123.1 (4)	C3—C2—H2A	119.9
N2—C11—C12	117.5 (4)	C1—C2—H2A	119.9
C7—C11—C12	119.4 (4)	N4—C22—C21	123.3 (4)
C9—C8—C7	121.0 (5)	N4—C22—H22A	118.4
C9—C8—H8A	119.5	C21—C22—H22A	118.4
C7—C8—H8A	119.5	C20—C21—C22	119.6 (4)
C13—C15—C16	118.6 (5)	C20—C21—H21A	120.2
C13—C15—H15A	120.7	C22—C21—H21A	120.2
C16—C15—H15A	120.7	N1—C1—C2	121.8 (4)
N3—C14—C13	122.6 (4)	N1—C1—H1A	119.1
N3—C14—H14A	118.7	C2—C1—H1A	119.1
C13—C14—H14A	118.7	S1—O1—Cu1	129.51 (18)
N2—C10—C9	122.7 (5)	C26—O6—H6B	109.5
N2—C10—H10A	118.6	C25—O5—H5B	109.5
C9—C10—H10A	118.6	O6—C26—C25	115.7 (6)
N1—C12—C4	123.3 (4)	O6—C26—H26A	108.3
N1—C12—C11	117.1 (4)	C25—C26—H26A	108.3
C4—C12—C11	119.7 (4)	O6—C26—H26B	108.3
C20—C19—C18	125.2 (4)	C25—C26—H26B	108.3
C20—C19—C23	116.4 (4)	H26A—C26—H26B	107.4
C18—C19—C23	118.4 (4)	O5—C25—C26	113.3 (5)
C12—C4—C3	117.4 (4)	O5—C25—H25A	108.9
C12—C4—C5	120.2 (4)	C26—C25—H25A	108.9
C3—C4—C5	122.4 (4)	O5—C25—H25B	108.9
C14—C13—C15	119.9 (5)	C26—C25—H25B	108.9
C14—C13—H13A	120.0	H25A—C25—H25B	107.7
C15—C13—H13A	120.0
O1—Cu1—N3—C14	−37.2 (4)	N2—C10—C9—C8	−1.8 (7)
N4—Cu1—N3—C14	178.8 (4)	C20—C19—C18—C17	−179.6 (5)
N1—Cu1—N3—C14	67.4 (4)	C23—C19—C18—C17	−0.2 (7)
O1—Cu1—N3—C24	147.5 (3)	C12—C4—C5—C6	−0.1 (7)
N4—Cu1—N3—C24	3.5 (3)	C3—C4—C5—C6	179.7 (5)
N1—Cu1—N3—C24	−107.9 (3)	C9—C8—C7—C11	1.2 (7)
O1—Cu1—N2—C10	−76.9 (4)	C9—C8—C7—C6	−178.6 (4)
N4—Cu1—N2—C10	68.3 (4)	N2—C11—C7—C8	−1.6 (6)
N1—Cu1—N2—C10	179.6 (4)	C12—C11—C7—C8	178.5 (4)
O1—Cu1—N2—C11	105.0 (3)	N2—C11—C7—C6	178.2 (4)
N4—Cu1—N2—C11	−109.8 (3)	C12—C11—C7—C6	−1.6 (6)
N1—Cu1—N2—C11	1.5 (3)	N3—C24—C16—C15	−1.2 (7)
C14—N3—C24—C16	1.2 (7)	C23—C24—C16—C15	−179.3 (4)
Cu1—N3—C24—C16	176.9 (3)	N3—C24—C16—C17	176.7 (4)
C14—N3—C24—C23	179.4 (4)	C23—C24—C16—C17	−1.4 (7)
Cu1—N3—C24—C23	−4.9 (5)	C13—C15—C16—C24	−0.2 (7)
O1—Cu1—N1—C1	83.4 (4)	C13—C15—C16—C17	−178.1 (5)
N2—Cu1—N1—C1	178.1 (4)	C19—C18—C17—C16	0.2 (7)
N3—Cu1—N1—C1	−9.1 (4)	C24—C16—C17—C18	0.6 (7)
N4—Cu1—N1—C1	−91.2 (4)	C15—C16—C17—C18	178.4 (5)
O1—Cu1—N1—C12	−95.9 (3)	C12—C4—C3—C2	−1.0 (7)
N2—Cu1—N1—C12	−1.1 (3)	C5—C4—C3—C2	179.2 (5)
N3—Cu1—N1—C12	171.7 (3)	C22—N4—C23—C19	2.7 (6)
N4—Cu1—N1—C12	89.6 (3)	Cu1—N4—C23—C19	180.0 (3)
O1—Cu1—N4—C22	94.6 (4)	C22—N4—C23—C24	−178.0 (4)
N2—Cu1—N4—C22	−12.9 (4)	Cu1—N4—C23—C24	−0.7 (5)
N3—Cu1—N4—C22	175.3 (4)	C20—C19—C23—N4	−1.8 (6)
N1—Cu1—N4—C22	−94.2 (4)	C18—C19—C23—N4	178.8 (4)
O1—Cu1—N4—C23	−82.1 (3)	C20—C19—C23—C24	178.9 (4)
N2—Cu1—N4—C23	170.3 (3)	C18—C19—C23—C24	−0.5 (6)
N3—Cu1—N4—C23	−1.5 (3)	N3—C24—C23—N4	3.7 (6)
N1—Cu1—N4—C23	89.0 (3)	C16—C24—C23—N4	−178.0 (4)
C10—N2—C11—C7	0.2 (7)	N3—C24—C23—C19	−176.9 (4)
Cu1—N2—C11—C7	178.5 (3)	C16—C24—C23—C19	1.3 (6)
C10—N2—C11—C12	−179.9 (4)	C4—C5—C6—C7	1.2 (8)
Cu1—N2—C11—C12	−1.6 (5)	C8—C7—C6—C5	179.5 (5)
C24—N3—C14—C13	0.4 (7)	C11—C7—C6—C5	−0.3 (7)
Cu1—N3—C14—C13	−174.7 (4)	C18—C19—C20—C21	179.3 (4)
C11—N2—C10—C9	1.5 (7)	C23—C19—C20—C21	−0.1 (7)
Cu1—N2—C10—C9	−176.5 (3)	C4—C3—C2—C1	1.5 (7)
C1—N1—C12—C4	−1.0 (6)	C23—N4—C22—C21	−1.7 (7)
Cu1—N1—C12—C4	178.3 (3)	Cu1—N4—C22—C21	−178.3 (4)
C1—N1—C12—C11	−178.7 (4)	C19—C20—C21—C22	1.0 (7)
Cu1—N1—C12—C11	0.7 (5)	N4—C22—C21—C20	−0.1 (8)
N2—C11—C12—N1	0.6 (6)	C12—N1—C1—C2	1.6 (6)
C7—C11—C12—N1	−179.6 (4)	Cu1—N1—C1—C2	−177.6 (3)
N2—C11—C12—C4	−177.2 (4)	C3—C2—C1—N1	−1.9 (7)
C7—C11—C12—C4	2.7 (6)	O4—S1—O1—Cu1	−145.3 (2)
N1—C12—C4—C3	0.7 (7)	O2—S1—O1—Cu1	−26.9 (3)
C11—C12—C4—C3	178.3 (4)	O3—S1—O1—Cu1	94.2 (3)
N1—C12—C4—C5	−179.4 (4)	N2—Cu1—O1—S1	72.8 (3)
C11—C12—C4—C5	−1.8 (6)	N3—Cu1—O1—S1	−111.3 (3)
N3—C14—C13—C15	−1.8 (8)	N4—Cu1—O1—S1	−33.9 (4)
C16—C15—C13—C14	1.6 (8)	N1—Cu1—O1—S1	154.6 (2)
C7—C8—C9—C10	0.3 (7)	O6—C26—C25—O5	71.3 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6B···O4	0.82	1.93	2.751 (5)	176.
O5—H5B···O3	0.82	1.98	2.798 (5)	171.

Table 1

Selected geometric parameters (Å, °)

Cu1—O1	1.957 (3)
Cu1—N2	1.990 (4)
Cu1—N3	2.006 (4)
Cu1—N4	2.073 (4)
Cu1—N1	2.162 (4)
S1—O4	1.469 (3)
S1—O2	1.470 (3)
S1—O3	1.475 (3)
S1—O1	1.504 (3)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H6B⋯O4	0.82	1.93	2.751 (5)	176
O5—H5B⋯O3	0.82	1.98	2.798 (5)	171