A new polymorph of aqua-bis-(1,10-phenanthroline-κ(2) N,N')copper(II) dinitrate.

The title mol-ecule, [Cu(C12H8N2)2(H2O)](NO3)2, is a new polymorph of a compound which up to now has been reported to crystallize space groups in C2/c and Cc. The crystal studied was twinned by non-merohedry (final BASF factor of 0.40043) with the structure being solved and refined in P-1. The Cu(II) atom is coordinated by four N atoms from two 1,10-phenanthroline ligands and an O atom from a water mol-ecule in an approximate trigonal-bipyramidal geometry. Discrete entities of one cation and two nitrate anions are formed by water-nitrate O-H⋯O hydrogen bonds. The components are further assembled into a three-dimensional network by C-H⋯O hydrogen bonds.

Related literature

For structural analyses of the other polymorphs, see: Nakai & Deguchi (1975 ▶); Catalan et al. (1995 ▶); Szpakolski et al. (2010 ▶); Zhou (2011 ▶).

Experimental

Crystal data

[Cu(C12H8N2)2(H2O)](NO3)2

M = 565.99

Triclinic,

a = 7.0836 (3) Å

b = 11.7898 (3) Å

c = 14.2951 (4) Å

α = 78.079 (2)°

β = 79.862 (3)°

γ = 73.782 (3)°

V = 1112.68 (7) Å3

Z = 2

Mo Kα radiation

μ = 1.05 mm−1

T = 150 K

0.12 × 0.10 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer

17314 measured reflections

11903 independent reflections

10562 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.172

S = 1.17

11903 reflections

344 parameters

3 restraints

H-atom parameters constrained

Δρmax = 0.98 e Å−3

Δρmin = −0.63 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ATOMS (Dowty, 1995 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814008198/im2451sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814008198/im2451Isup2.hkl

CCDC reference: 996861

Additional supporting information: crystallographic information; 3D view; checkCIF report

[Cu(C12H8N2)2(H2O)](NO3)2	Z = 2
Mr = 565.99	F(000) = 578
Triclinic, P1	Dx = 1.689 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.0836 (3) Å	Cell parameters from 11062 reflections
b = 11.7898 (3) Å	θ = 1.8–34.6°
c = 14.2951 (4) Å	µ = 1.05 mm−1
α = 78.079 (2)°	T = 150 K
β = 79.862 (3)°	Block, green
γ = 73.782 (3)°	0.12 × 0.10 × 0.08 mm
V = 1112.68 (7) Å3

Bruker APEXII CCD diffractometer	10562 reflections with I > 2σ(I)
Radiation source: Rotating Anode	Rint = 0.041
Graphite monochromator	θmax = 27.9°, θmin = 2.1°
Detector resolution: 18.4 pixels mm-1	h = −9→9
φ and ω scans	k = −15→15
17314 measured reflections	l = −18→18
11903 independent reflections

Refinement on F2	3 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.058	H-atom parameters constrained
wR(F2) = 0.172	w = 1/[Σ2(FO2) + (0.0916P)2 + 1.1415P] where P = (FO2 + 2FC2)/3
S = 1.17	(Δ/σ)max = 0.001
11903 reflections	Δρmax = 0.98 e Å−3
344 parameters	Δρmin = −0.63 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > 2sigma(F2) is used only for calculating -R-factor-obs 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
Cu01	0.88124 (7)	0.26741 (4)	0.24554 (3)	0.0110 (1)
O1W	1.1790 (4)	0.2580 (3)	0.2736 (2)	0.0211 (9)
N1	0.9959 (5)	0.0992 (3)	0.2189 (2)	0.0107 (8)
N2	0.7695 (5)	0.1813 (3)	0.3734 (2)	0.0102 (8)
N3	0.8143 (5)	0.3546 (3)	0.1125 (2)	0.0108 (8)
N4	0.8066 (5)	0.4349 (3)	0.2743 (2)	0.0106 (8)
C1	1.1142 (6)	0.0599 (3)	0.1420 (3)	0.0138 (10)
C2	1.2069 (6)	−0.0618 (4)	0.1400 (3)	0.0166 (11)
C3	1.1773 (6)	−0.1452 (3)	0.2200 (3)	0.0157 (11)
C4	1.0526 (6)	−0.1077 (3)	0.3020 (3)	0.0123 (10)
C5	1.0093 (6)	−0.1886 (3)	0.3887 (3)	0.0158 (11)
C6	0.8865 (6)	−0.1471 (4)	0.4654 (3)	0.0165 (11)
C7	0.8004 (6)	−0.0215 (3)	0.4637 (3)	0.0130 (10)
C8	0.6764 (6)	0.0268 (4)	0.5424 (3)	0.0165 (11)
C9	0.6022 (6)	0.1487 (4)	0.5337 (3)	0.0159 (11)
C10	0.6507 (6)	0.2242 (4)	0.4478 (3)	0.0144 (10)
C11	0.9666 (5)	0.0160 (3)	0.2980 (3)	0.0106 (10)
C12	0.8408 (5)	0.0607 (3)	0.3808 (3)	0.0102 (9)
C13	0.8086 (6)	0.3120 (3)	0.0336 (3)	0.0129 (10)
C14	0.7705 (6)	0.3877 (4)	−0.0548 (3)	0.0147 (11)
C15	0.7352 (6)	0.5097 (4)	−0.0617 (3)	0.0143 (10)
C16	0.7332 (5)	0.5576 (3)	0.0216 (3)	0.0115 (10)
C17	0.6900 (6)	0.6839 (3)	0.0236 (3)	0.0146 (10)
C18	0.6955 (6)	0.7250 (3)	0.1053 (3)	0.0143 (10)
C19	0.7375 (5)	0.6431 (3)	0.1932 (3)	0.0120 (10)
C20	0.7436 (6)	0.6794 (3)	0.2806 (3)	0.0133 (10)
C21	0.7790 (6)	0.5936 (3)	0.3618 (3)	0.0145 (11)
C22	0.8106 (6)	0.4717 (3)	0.3562 (3)	0.0125 (10)
C23	0.7737 (5)	0.4760 (3)	0.1066 (3)	0.0099 (9)
C24	0.7716 (5)	0.5196 (3)	0.1939 (3)	0.0103 (10)
O1	0.6976 (6)	0.0152 (3)	0.0982 (2)	0.0341 (11)
O2	0.5277 (5)	0.1630 (3)	0.1717 (2)	0.0251 (9)
O3	0.5629 (5)	−0.0219 (3)	0.2460 (2)	0.0229 (9)
N5	0.5964 (5)	0.0505 (3)	0.1718 (2)	0.0143 (9)
O4	1.2876 (6)	0.5301 (3)	0.2707 (2)	0.0291 (10)
O5	1.3245 (5)	0.5481 (3)	0.4138 (2)	0.0242 (9)
O6	1.2436 (5)	0.3916 (3)	0.3929 (2)	0.0204 (8)
N6	1.2854 (5)	0.4914 (3)	0.3584 (2)	0.0143 (9)
H1	1.13600	0.11560	0.08750	0.0170*
H1W	1.28200	0.23300	0.24360	0.0220*
H2	1.28740	−0.08550	0.08510	0.0200*
H2W	1.19590	0.31520	0.29900	0.0220*
H3	1.23910	−0.22600	0.22000	0.0190*
H5	1.06640	−0.27040	0.39210	0.0190*
H6	0.85780	−0.20120	0.51990	0.0200*
H8	0.64570	−0.02320	0.59910	0.0200*
H9	0.51940	0.18170	0.58470	0.0190*
H10	0.59810	0.30650	0.44320	0.0170*
H13	0.83060	0.22980	0.03720	0.0150*
H14	0.76920	0.35510	−0.10850	0.0180*
H15	0.71300	0.56000	−0.12020	0.0170*
H17	0.65770	0.73840	−0.03180	0.0180*
H18	0.67180	0.80690	0.10420	0.0170*
H20	0.72390	0.76000	0.28340	0.0160*
H21	0.78200	0.61630	0.42000	0.0170*
H22	0.83510	0.41490	0.41130	0.0150*

	U11	U22	U33	U12	U13	U23
Cu01	0.0172 (3)	0.0060 (2)	0.0083 (2)	−0.0009 (2)	−0.0024 (2)	0.0000 (2)
O1W	0.0146 (14)	0.0201 (15)	0.0317 (16)	−0.0024 (12)	−0.0021 (12)	−0.0148 (13)
N1	0.0125 (15)	0.0102 (15)	0.0102 (14)	−0.0040 (12)	−0.0032 (11)	−0.0002 (11)
N2	0.0110 (15)	0.0111 (15)	0.0096 (14)	−0.0031 (12)	−0.0049 (11)	−0.0010 (11)
N3	0.0130 (15)	0.0092 (14)	0.0099 (14)	−0.0026 (12)	−0.0022 (11)	−0.0005 (11)
N4	0.0115 (15)	0.0081 (14)	0.0108 (14)	−0.0005 (12)	−0.0027 (11)	0.0002 (11)
C1	0.0154 (18)	0.0138 (18)	0.0122 (17)	−0.0034 (15)	−0.0023 (14)	−0.0022 (14)
C2	0.0155 (19)	0.0184 (19)	0.0164 (19)	−0.0011 (15)	−0.0027 (15)	−0.0077 (15)
C3	0.0165 (19)	0.0092 (17)	0.022 (2)	0.0004 (15)	−0.0066 (15)	−0.0054 (14)
C4	0.0140 (18)	0.0093 (17)	0.0161 (18)	−0.0052 (14)	−0.0070 (14)	0.0000 (13)
C5	0.0183 (19)	0.0083 (17)	0.023 (2)	−0.0062 (15)	−0.0109 (16)	0.0033 (14)
C6	0.020 (2)	0.0142 (18)	0.0170 (19)	−0.0097 (16)	−0.0078 (15)	0.0058 (14)
C7	0.0124 (17)	0.0143 (18)	0.0148 (18)	−0.0077 (14)	−0.0068 (14)	0.0025 (14)
C8	0.0141 (18)	0.027 (2)	0.0106 (17)	−0.0117 (17)	−0.0031 (14)	0.0020 (15)
C9	0.0128 (18)	0.025 (2)	0.0106 (17)	−0.0062 (16)	−0.0013 (14)	−0.0027 (15)
C10	0.0130 (17)	0.0174 (19)	0.0133 (17)	−0.0031 (15)	−0.0032 (14)	−0.0034 (14)
C11	0.0109 (17)	0.0102 (17)	0.0113 (16)	−0.0029 (14)	−0.0047 (13)	−0.0003 (13)
C12	0.0094 (16)	0.0114 (17)	0.0108 (16)	−0.0042 (14)	−0.0038 (13)	0.0003 (13)
C13	0.0138 (18)	0.0114 (17)	0.0137 (18)	−0.0034 (14)	−0.0022 (14)	−0.0022 (14)
C14	0.0154 (18)	0.020 (2)	0.0095 (17)	−0.0039 (16)	−0.0043 (14)	−0.0026 (14)
C15	0.0150 (18)	0.0174 (19)	0.0100 (17)	−0.0040 (15)	−0.0044 (14)	0.0014 (14)
C16	0.0084 (16)	0.0144 (18)	0.0107 (17)	−0.0031 (14)	−0.0033 (13)	0.0023 (13)
C17	0.0138 (18)	0.0118 (18)	0.0149 (18)	−0.0025 (15)	−0.0031 (14)	0.0054 (14)
C18	0.0116 (17)	0.0097 (17)	0.0188 (19)	−0.0003 (14)	−0.0023 (14)	0.0007 (14)
C19	0.0092 (16)	0.0096 (17)	0.0148 (17)	−0.0001 (14)	−0.0005 (13)	−0.0010 (13)
C20	0.0129 (17)	0.0083 (17)	0.0188 (19)	−0.0026 (14)	−0.0006 (14)	−0.0039 (14)
C21	0.0178 (19)	0.0132 (18)	0.0137 (18)	−0.0031 (15)	−0.0019 (14)	−0.0058 (14)
C22	0.0146 (18)	0.0098 (17)	0.0118 (17)	−0.0024 (14)	−0.0029 (14)	0.0009 (13)
C23	0.0080 (16)	0.0094 (16)	0.0116 (17)	−0.0018 (13)	−0.0019 (13)	−0.0004 (13)
C24	0.0086 (16)	0.0098 (17)	0.0117 (17)	−0.0008 (14)	−0.0033 (13)	−0.0001 (13)
O1	0.050 (2)	0.0320 (19)	0.0223 (16)	−0.0173 (17)	0.0127 (15)	−0.0140 (14)
O2	0.0237 (16)	0.0130 (14)	0.0312 (17)	−0.0005 (12)	0.0022 (13)	0.0023 (12)
O3	0.0301 (17)	0.0167 (15)	0.0186 (15)	−0.0072 (13)	−0.0020 (12)	0.0053 (11)
N5	0.0136 (16)	0.0152 (16)	0.0143 (15)	−0.0048 (13)	−0.0033 (12)	0.0003 (12)
O4	0.044 (2)	0.0313 (18)	0.0126 (14)	−0.0133 (16)	−0.0072 (13)	0.0035 (12)
O5	0.0317 (17)	0.0230 (16)	0.0228 (16)	−0.0091 (14)	−0.0097 (13)	−0.0067 (12)
O6	0.0288 (16)	0.0150 (14)	0.0193 (14)	−0.0079 (13)	−0.0094 (12)	0.0014 (11)
N6	0.0125 (15)	0.0132 (16)	0.0156 (16)	0.0001 (13)	−0.0039 (12)	−0.0016 (12)

Cu01—O1W	2.184 (3)	C9—C10	1.410 (6)
Cu01—N1	2.010 (3)	C11—C12	1.448 (6)
Cu01—N2	2.042 (3)	C13—C14	1.409 (6)
Cu01—N3	2.034 (3)	C14—C15	1.375 (6)
Cu01—N4	2.006 (3)	C15—C16	1.416 (6)
O1W—H1W	0.7900	C16—C17	1.439 (5)
O1W—H2W	0.8700	C16—C23	1.404 (6)
O1—N5	1.242 (4)	C17—C18	1.364 (6)
O2—N5	1.279 (5)	C18—C19	1.439 (6)
O3—N5	1.249 (4)	C19—C24	1.406 (5)
O4—N6	1.241 (4)	C19—C20	1.413 (6)
O5—N6	1.245 (5)	C20—C21	1.382 (6)
O6—N6	1.272 (5)	C21—C22	1.408 (5)
N1—C1	1.340 (5)	C23—C24	1.441 (6)
N1—C11	1.363 (5)	C1—H1	0.9300
N2—C12	1.358 (5)	C2—H2	0.9300
N2—C10	1.328 (5)	C3—H3	0.9300
N3—C13	1.337 (5)	C5—H5	0.9300
N3—C23	1.366 (5)	C6—H6	0.9300
N4—C22	1.337 (5)	C8—H8	0.9300
N4—C24	1.367 (5)	C9—H9	0.9300
C1—C2	1.405 (6)	C10—H10	0.9300
C2—C3	1.373 (6)	C13—H13	0.9300
C3—C4	1.408 (6)	C14—H14	0.9300
C4—C11	1.408 (5)	C15—H15	0.9300
C4—C5	1.443 (6)	C17—H17	0.9300
C5—C6	1.359 (6)	C18—H18	0.9300
C6—C7	1.432 (6)	C20—H20	0.9300
C7—C8	1.414 (6)	C21—H21	0.9300
C7—C12	1.409 (6)	C22—H22	0.9300
C8—C9	1.373 (6)
O1W—Cu01—N1	85.46 (14)	C13—C14—C15	120.1 (4)
O1W—Cu01—N2	101.65 (13)	C14—C15—C16	119.0 (4)
O1W—Cu01—N3	114.86 (13)	C15—C16—C23	117.3 (3)
O1W—Cu01—N4	86.34 (14)	C15—C16—C17	123.7 (4)
N1—Cu01—N2	82.61 (13)	C17—C16—C23	119.0 (4)
N1—Cu01—N3	100.51 (13)	C16—C17—C18	121.2 (4)
N1—Cu01—N4	171.78 (15)	C17—C18—C19	120.8 (3)
N2—Cu01—N3	143.48 (15)	C18—C19—C20	123.8 (3)
N2—Cu01—N4	99.69 (13)	C18—C19—C24	118.9 (4)
N3—Cu01—N4	82.40 (13)	C20—C19—C24	117.3 (4)
Cu01—O1W—H2W	118.00	C19—C20—C21	119.2 (3)
H1W—O1W—H2W	105.00	C20—C21—C22	119.8 (4)
Cu01—O1W—H1W	129.00	N4—C22—C21	122.2 (4)
C1—N1—C11	117.5 (3)	C16—C23—C24	119.8 (3)
Cu01—N1—C1	129.8 (3)	N3—C23—C16	123.5 (3)
Cu01—N1—C11	112.0 (2)	N3—C23—C24	116.7 (3)
Cu01—N2—C10	130.8 (3)	C19—C24—C23	120.2 (4)
Cu01—N2—C12	111.1 (3)	N4—C24—C19	123.4 (4)
C10—N2—C12	118.1 (3)	N4—C24—C23	116.3 (3)
C13—N3—C23	117.9 (3)	N1—C1—H1	119.00
Cu01—N3—C13	130.6 (3)	C2—C1—H1	119.00
Cu01—N3—C23	111.5 (2)	C1—C2—H2	120.00
Cu01—N4—C24	112.6 (2)	C3—C2—H2	120.00
Cu01—N4—C22	128.8 (3)	C4—C3—H3	120.00
C22—N4—C24	118.1 (3)	C2—C3—H3	120.00
O2—N5—O3	119.6 (3)	C4—C5—H5	119.00
O1—N5—O2	119.2 (3)	C6—C5—H5	120.00
O1—N5—O3	121.1 (3)	C7—C6—H6	119.00
O4—N6—O6	119.8 (3)	C5—C6—H6	119.00
O4—N6—O5	121.3 (4)	C7—C8—H8	121.00
O5—N6—O6	118.9 (3)	C9—C8—H8	121.00
N1—C1—C2	122.9 (4)	C8—C9—H9	120.00
C1—C2—C3	119.3 (4)	C10—C9—H9	120.00
C2—C3—C4	119.6 (3)	C9—C10—H10	119.00
C3—C4—C11	117.4 (4)	N2—C10—H10	119.00
C5—C4—C11	118.9 (4)	N3—C13—H13	119.00
C3—C4—C5	123.7 (3)	C14—C13—H13	119.00
C4—C5—C6	121.0 (3)	C13—C14—H14	120.00
C5—C6—C7	121.1 (4)	C15—C14—H14	120.00
C6—C7—C8	123.4 (4)	C16—C15—H15	121.00
C6—C7—C12	119.7 (4)	C14—C15—H15	121.00
C8—C7—C12	116.8 (3)	C16—C17—H17	119.00
C7—C8—C9	118.9 (4)	C18—C17—H17	119.00
C8—C9—C10	120.3 (4)	C17—C18—H18	120.00
N2—C10—C9	122.0 (4)	C19—C18—H18	120.00
N1—C11—C4	123.3 (4)	C21—C20—H20	120.00
C4—C11—C12	120.1 (4)	C19—C20—H20	120.00
N1—C11—C12	116.6 (3)	C20—C21—H21	120.00
N2—C12—C7	123.9 (3)	C22—C21—H21	120.00
N2—C12—C11	117.0 (3)	C21—C22—H22	119.00
C7—C12—C11	119.1 (3)	N4—C22—H22	119.00
N3—C13—C14	122.1 (3)
O1W—Cu01—N1—C1	−75.3 (4)	C22—N4—C24—C23	178.4 (4)
O1W—Cu01—N1—C11	95.0 (3)	N1—C1—C2—C3	−0.4 (7)
N2—Cu01—N1—C1	−177.7 (4)	C1—C2—C3—C4	0.9 (7)
N2—Cu01—N1—C11	−7.4 (3)	C2—C3—C4—C5	178.8 (4)
N3—Cu01—N1—C1	39.2 (4)	C2—C3—C4—C11	−1.3 (6)
N3—Cu01—N1—C11	−150.6 (3)	C3—C4—C5—C6	−179.5 (4)
O1W—Cu01—N2—C10	99.2 (4)	C11—C4—C5—C6	0.5 (6)
O1W—Cu01—N2—C12	−77.6 (3)	C3—C4—C11—N1	1.1 (6)
N1—Cu01—N2—C10	−177.0 (4)	C3—C4—C11—C12	−178.5 (4)
N1—Cu01—N2—C12	6.2 (3)	C5—C4—C11—N1	−178.9 (4)
N3—Cu01—N2—C10	−79.3 (4)	C5—C4—C11—C12	1.5 (6)
N3—Cu01—N2—C12	103.9 (3)	C4—C5—C6—C7	−1.7 (7)
N4—Cu01—N2—C10	11.0 (4)	C5—C6—C7—C8	−178.1 (4)
N4—Cu01—N2—C12	−165.8 (3)	C5—C6—C7—C12	1.0 (7)
O1W—Cu01—N3—C13	101.9 (4)	C6—C7—C8—C9	179.6 (4)
O1W—Cu01—N3—C23	−76.7 (3)	C12—C7—C8—C9	0.5 (6)
N1—Cu01—N3—C13	12.1 (4)	C6—C7—C12—N2	−178.5 (4)
N1—Cu01—N3—C23	−166.5 (3)	C6—C7—C12—C11	1.0 (6)
N2—Cu01—N3—C13	−79.7 (4)	C8—C7—C12—N2	0.6 (6)
N2—Cu01—N3—C23	101.8 (3)	C8—C7—C12—C11	−179.9 (4)
N4—Cu01—N3—C13	−175.7 (4)	C7—C8—C9—C10	−0.5 (7)
N4—Cu01—N3—C23	5.7 (3)	C8—C9—C10—N2	−0.6 (7)
O1W—Cu01—N4—C22	−62.0 (4)	N1—C11—C12—N2	−2.3 (5)
O1W—Cu01—N4—C24	109.3 (3)	N1—C11—C12—C7	178.1 (4)
N2—Cu01—N4—C22	39.2 (4)	C4—C11—C12—N2	177.3 (4)
N2—Cu01—N4—C24	−149.6 (3)	C4—C11—C12—C7	−2.2 (6)
N3—Cu01—N4—C22	−177.7 (4)	N3—C13—C14—C15	−0.8 (7)
N3—Cu01—N4—C24	−6.4 (3)	C13—C14—C15—C16	−1.5 (7)
Cu01—N1—C1—C2	170.0 (3)	C14—C15—C16—C17	−177.4 (4)
C11—N1—C1—C2	0.2 (6)	C14—C15—C16—C23	1.8 (6)
Cu01—N1—C11—C4	−172.1 (3)	C15—C16—C17—C18	−178.2 (4)
Cu01—N1—C11—C12	7.5 (4)	C23—C16—C17—C18	2.6 (6)
C1—N1—C11—C4	−0.6 (6)	C15—C16—C23—N3	0.0 (6)
C1—N1—C11—C12	179.0 (4)	C15—C16—C23—C24	−179.3 (4)
Cu01—N2—C10—C9	−174.9 (3)	C17—C16—C23—N3	179.3 (4)
C12—N2—C10—C9	1.7 (6)	C17—C16—C23—C24	−0.1 (6)
Cu01—N2—C12—C7	175.5 (3)	C16—C17—C18—C19	−2.4 (7)
Cu01—N2—C12—C11	−4.0 (4)	C17—C18—C19—C20	−179.3 (4)
C10—N2—C12—C7	−1.7 (6)	C17—C18—C19—C24	−0.4 (6)
C10—N2—C12—C11	178.7 (4)	C18—C19—C20—C21	177.9 (4)
Cu01—N3—C13—C14	−175.9 (3)	C24—C19—C20—C21	−1.0 (6)
C23—N3—C13—C14	2.6 (6)	C18—C19—C24—N4	−177.9 (4)
Cu01—N3—C23—C16	176.5 (3)	C18—C19—C24—C23	3.0 (6)
Cu01—N3—C23—C24	−4.1 (4)	C20—C19—C24—N4	1.1 (6)
C13—N3—C23—C16	−2.2 (6)	C20—C19—C24—C23	−178.1 (4)
C13—N3—C23—C24	177.1 (4)	C19—C20—C21—C22	0.7 (6)
Cu01—N4—C22—C21	171.3 (3)	C20—C21—C22—N4	−0.4 (7)
C24—N4—C22—C21	0.4 (6)	N3—C23—C24—N4	−1.3 (5)
Cu01—N4—C24—C19	−173.1 (3)	N3—C23—C24—C19	177.9 (4)
Cu01—N4—C24—C23	6.1 (4)	C16—C23—C24—N4	178.1 (4)
C22—N4—C24—C19	−0.7 (6)	C16—C23—C24—C19	−2.7 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O2i	0.79	1.92	2.709 (5)	176
O1W—H2W···O6	0.87	1.89	2.718 (5)	159
C2—H2···O1ii	0.93	2.57	3.313 (5)	137
C5—H5···O5iii	0.93	2.40	3.271 (5)	156
C6—H6···O6iv	0.93	2.56	3.417 (6)	154
C8—H8···O3v	0.93	2.50	3.194 (5)	131
C10—H10···O6vi	0.93	2.60	3.131 (6)	117
C14—H14···O4vii	0.93	2.47	3.102 (5)	125
C15—H15···O4vii	0.93	2.59	3.157 (5)	120
C17—H17···O2viii	0.93	2.49	3.363 (5)	157
C18—H18···O1ix	0.93	2.50	3.406 (5)	166
C20—H20···O3ix	0.93	2.49	3.357 (5)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W⋯O2i	0.79	1.92	2.709 (5)	176
O1W—H2W⋯O6	0.87	1.89	2.718 (5)	159
C2—H2⋯O1ii	0.93	2.57	3.313 (5)	137
C5—H5⋯O5iii	0.93	2.40	3.271 (5)	156
C6—H6⋯O6iv	0.93	2.56	3.417 (6)	154
C8—H8⋯O3v	0.93	2.50	3.194 (5)	131
C17—H17⋯O2vi	0.93	2.49	3.363 (5)	157
C18—H18⋯O1vii	0.93	2.50	3.406 (5)	166
C20—H20⋯O3vii	0.93	2.49	3.357 (5)	155

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) .