μ-4,4′-Bipyridine-κ²N:N′-bis­[aqua(nitrato-κO)(1,10-phenanthroline-κ²N,N′)copper(II)] dinitrate

The title compound, [Cu₂(NO₃)₂(C₁₀H₈N₂)(C₁₂H₈N₂)₂(H₂O)₂](NO₃)₂, comprises a binuclear copper complex cation and two nitrate anions. In the doubly-charged bridged dicopper cation, each Cu atom is five-coordinated in a distorted square-pyramidal geometry, formed by one O atom of the coordinated water mol­ecule, one O atom of a coordinated nitrate anion, two N atoms from the bidentate 1,10-phenanthroline (phen) ligand and another N atom from the 4,4′-bipyridine (bipy) ligand. The bipy ligand bridges the Cu atoms to give a centrosymmetric binuclear structure. The complex is stabilized by hydrogen bonds and aromatic ring-stacking inter­actions [average inter­planar distance 3.3139 (2) Å and ring-centroid separation 3.7971 (9) Å.

Key indicators

• Single-crystal X-ray study
• T = 291 K
• Mean [sigma](C-C) = 0.009 Å
• R factor = 0.050
• wR factor = 0.227
• Data-to-parameter ratio = 11.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.99
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O2
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C15
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         N5
PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          9
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         13
            N3  -CU1 -N2  -C1   -148.80  1.30   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         17
            N3  -CU1 -N2  -C12    31.20  1.50   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         22
            N2  -CU1 -N3  -C13  -112.00  1.40   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         26
            N2  -CU1 -N3  -C17    59.00  1.50   1.555   1.555   1.555   1.555

Alert level G
PLAT794_ALERT_5_G Check Predicted Bond Valency for Cu1         (2)       2.11

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  10 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   6 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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S1. Comment

In the previous literatures, binuclear copper complexes containing (phen-Cu-bipy-Cu-phen) subunit (Blake et al., 1998; Wu et al., 2002; Lin et al., 2005) have been reported. In our paper, we describe another new compound containing (phen-Cu-bipy-Cu-phen) subunit, (I), (Fig.1).

Compound (I) is comprised of a binuclear copper complex cation and two nitrate anions. In the doubly charged bridged dicopper cation, each Cu center has distorted square-pyramidal geometry, formed by one O atom of the coordinated water molecule, one O atom of coordinated nitrate anion, two N atoms from bidentate 1,10-phenanthroline (phen) ligand and another N atom from 4,4'-bipyridine (bipy) (Table 1). The plane N1/N2/O1/N3 defines the base of the pyramid while water O7 occupies the apex. The distance from Cu1 to the least-squares plane N1/N2/O1/N3 is 0.1924 (4)Å towards O7. The bipy ligand bridge the Cu atoms to give this binuclear structure.

The water molecules and coordinated nitrate O atoms take part in intermolecular hydrogen bonds interactions and they join complex cations into a one-dimensional chain structure along a axis (Fig. 2 and Table 2). The chains are further expanded into two-dimensional network via the π-π stacking between 1,10-phenanthroline rings of adjacent chains of (I) (Fig. 3). The dihedral angle of aromatics involved in stacking is 0.0002 (3)°. Interplanar average distance and ring-centroid separation distance are 3.3139 (2) Å, 3.7971 (9) Å, respectively.

Related literature

For related literature, see: Blake et al. (1998); Wu et al. (2002); Lin et al. (2005).

S2. Experimental

A 10 ml water solution of Cu(NO)₃.3H₂O (0.242 g,1 mmol) was dropped into 10 ml me thanol solution of 4,4'-bipyridine (0.078 g, 0.5 mmol) and 1,10-phenanthroline (0.18 g,1 mmol) to be stirred for 4 h at 333 K. The filtrate stayed in air for about one week to obtain blue block-shaped crystals. Analysis, found (%): C 43.85, H 3.05, N 15.16. C₃₄H₂₈Cu₂N₁₀O₁₄ requires (%): C 43.98, H 3.02, N 15.09.

S3. Refinement

H atoms were positioned geometrically with C—H = 0.93 Å, O—H = 0.82 Å, and treated as riding atoms, with U_iso(H) = 1.2U_eq(C) or 1.5U_eq(O).

Computing details

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2; data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2004); software used to prepare material for publication: SHELXTL.

Figures

	Fig. 1. The molecular structure of (I), showing the atom-numbering scheme. Atoms with the suffix A are are at the symmetry position (-x + 1, -y + 2, -z + 1).
	Fig. 2. Packing diagram, showing the one-dimensional chain structure of (I), linked via hydrogen bonds (dashed lines). H atoms on C atoms and uncoordinated nitrate anions have been omitted for clarity.
	Fig. 3. The π–π stacking diagram between 1,10-phenanthroline rings of adjacent chains of (I). H atoms on C atoms and uncoordinated nitrate anions have been omitted.

µ-4,4'-Bipyridine-κ²N:N'-bis[aqua(nitrato-κO)(1,10- phenanthroline-κ²N,N')copper(II)] dinitrate

Crystal data

[Cu2(NO3)2(C10H8N2)(C12H8N2)2(H2O)2](NO3)2	Z = 1
Mr = 927.76	F(000) = 472
Triclinic, P1	Dx = 1.723 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3754 (18) Å	Cell parameters from 3225 reflections
b = 8.925 (2) Å	θ = 2.7–27.0°
c = 13.812 (3) Å	µ = 1.28 mm^−1
α = 92.347 (2)°	T = 291 K
β = 97.596 (2)°	Block, blue
γ = 96.311 (3)°	0.37 × 0.27 × 0.21 mm
V = 894.3 (4) Å^3

Data collection

Bruker APEXII CCD area-detector diffractometer	3200 independent reflections
Radiation source: fine-focus sealed tube	2909 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
φ and ω scans	θmax = 25.5°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.647, Tmax = 0.776	k = −10→10
6155 measured reflections	l = −16→16

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.227	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.183P)^2 + 1.6705P] where P = (Fo^2 + 2Fc^2)/3
3200 reflections	(Δ/σ)max < 0.001
271 parameters	Δρmax = 0.89 e Å^−3
0 restraints	Δρmin = −0.76 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cu1	0.69132 (8)	0.51338 (6)	0.71023 (4)	0.0247 (3)
O1	0.8055 (5)	0.4093 (5)	0.6066 (3)	0.0350 (9)
O2	1.0496 (6)	0.5437 (6)	0.6817 (3)	0.0462 (11)
O3	1.0720 (6)	0.3763 (6)	0.5659 (3)	0.0506 (12)
O4	0.4104 (7)	0.0751 (6)	0.7586 (4)	0.0540 (12)
O5	0.1351 (9)	0.0598 (9)	0.6823 (5)	0.082 (2)
O6	0.1944 (10)	−0.0793 (7)	0.8020 (5)	0.0754 (18)
O7	0.4292 (6)	0.3593 (5)	0.6762 (4)	0.0452 (11)
H1W	0.4431	0.2774	0.6993	0.068*
H2W	0.3303	0.3587	0.6404	0.068*
N1	0.6613 (6)	0.6354 (5)	0.8332 (3)	0.0260 (9)
N2	0.7736 (6)	0.3662 (5)	0.8101 (3)	0.0255 (9)
N3	0.6235 (7)	0.6792 (5)	0.6252 (3)	0.0321 (10)
N4	0.9803 (6)	0.4446 (5)	0.6181 (3)	0.0322 (10)
N5	0.2454 (8)	0.0181 (6)	0.7465 (4)	0.0423 (12)
C1	0.8307 (8)	0.2313 (6)	0.7951 (4)	0.0328 (12)
H1	0.8363	0.1960	0.7314	0.039*
C2	0.8818 (8)	0.1423 (7)	0.8717 (5)	0.0381 (13)
H2A	0.9207	0.0487	0.8589	0.046*
C3	0.8750 (8)	0.1918 (7)	0.9661 (5)	0.0397 (14)
H3A	0.9084	0.1318	1.0174	0.048*
C4	0.8170 (7)	0.3343 (6)	0.9852 (4)	0.0293 (11)
C5	0.8056 (8)	0.3986 (7)	1.0814 (4)	0.0358 (13)
H5A	0.8374	0.3448	1.1361	0.043*
C6	0.7489 (8)	0.5364 (7)	1.0925 (4)	0.0370 (13)
H6A	0.7435	0.5761	1.1552	0.044*
C7	0.6971 (7)	0.6229 (6)	1.0106 (4)	0.0314 (12)
C8	0.6355 (8)	0.7680 (7)	1.0179 (4)	0.0371 (13)
H8	0.6265	0.8132	1.0786	0.044*
C9	0.5897 (8)	0.8397 (6)	0.9341 (5)	0.0379 (13)
H9	0.5496	0.9347	0.9379	0.045*
C10	0.6025 (8)	0.7715 (6)	0.8425 (4)	0.0323 (12)
H10	0.5693	0.8221	0.7865	0.039*
C11	0.7076 (7)	0.5630 (6)	0.9160 (4)	0.0244 (10)
C12	0.7669 (7)	0.4173 (6)	0.9032 (4)	0.0249 (10)
C13	0.4474 (9)	0.6993 (7)	0.5978 (5)	0.0449 (15)
H13	0.3561	0.6266	0.6122	0.054*
C14	0.3950 (9)	0.8222 (7)	0.5495 (5)	0.0401 (14)
H14	0.2706	0.8314	0.5325	0.048*
C15	0.5268 (8)	0.9328 (6)	0.5258 (4)	0.0295 (11)
C16	0.7091 (10)	0.9111 (8)	0.5549 (6)	0.0521 (18)
H16	0.8029	0.9818	0.5407	0.063*
C17	0.7528 (9)	0.7864 (8)	0.6044 (5)	0.0480 (17)
H17	0.8761	0.7760	0.6241	0.058*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0303 (4)	0.0238 (4)	0.0218 (4)	0.0077 (3)	0.0047 (3)	0.0055 (3)
O1	0.029 (2)	0.047 (2)	0.0290 (19)	0.0074 (17)	0.0032 (15)	−0.0030 (16)
O2	0.040 (2)	0.055 (3)	0.043 (2)	0.001 (2)	0.0053 (19)	0.000 (2)
O3	0.047 (3)	0.072 (3)	0.041 (2)	0.033 (2)	0.015 (2)	0.009 (2)
O4	0.050 (3)	0.050 (3)	0.060 (3)	0.002 (2)	0.001 (2)	0.008 (2)
O5	0.059 (3)	0.100 (5)	0.083 (4)	0.008 (3)	−0.011 (3)	0.036 (4)
O6	0.085 (4)	0.057 (3)	0.090 (4)	0.010 (3)	0.027 (3)	0.039 (3)
O7	0.033 (2)	0.035 (2)	0.064 (3)	0.0007 (18)	−0.007 (2)	0.014 (2)
N1	0.028 (2)	0.024 (2)	0.027 (2)	0.0036 (17)	0.0069 (17)	0.0044 (16)
N2	0.025 (2)	0.022 (2)	0.030 (2)	0.0051 (17)	0.0061 (17)	0.0044 (17)
N3	0.041 (3)	0.031 (2)	0.027 (2)	0.009 (2)	0.0051 (19)	0.0078 (18)
N4	0.033 (2)	0.040 (3)	0.026 (2)	0.010 (2)	0.0070 (18)	0.0111 (19)
N5	0.054 (3)	0.031 (3)	0.045 (3)	0.010 (2)	0.014 (2)	0.004 (2)
C1	0.032 (3)	0.026 (3)	0.042 (3)	0.004 (2)	0.006 (2)	0.007 (2)
C2	0.038 (3)	0.025 (3)	0.053 (4)	0.008 (2)	0.003 (3)	0.008 (2)
C3	0.033 (3)	0.037 (3)	0.050 (4)	0.006 (3)	0.002 (2)	0.023 (3)
C4	0.023 (2)	0.032 (3)	0.032 (3)	0.000 (2)	0.002 (2)	0.011 (2)
C5	0.032 (3)	0.047 (3)	0.025 (3)	−0.003 (3)	−0.003 (2)	0.014 (2)
C6	0.032 (3)	0.053 (4)	0.024 (3)	−0.006 (3)	0.003 (2)	−0.002 (2)
C7	0.025 (3)	0.037 (3)	0.032 (3)	−0.003 (2)	0.008 (2)	−0.001 (2)
C8	0.037 (3)	0.038 (3)	0.035 (3)	−0.002 (2)	0.009 (2)	−0.011 (2)
C9	0.038 (3)	0.027 (3)	0.051 (4)	0.004 (2)	0.015 (3)	−0.005 (2)
C10	0.038 (3)	0.023 (3)	0.037 (3)	0.007 (2)	0.007 (2)	0.002 (2)
C11	0.020 (2)	0.027 (3)	0.026 (2)	−0.0016 (19)	0.0067 (18)	0.0010 (19)
C12	0.020 (2)	0.028 (3)	0.028 (2)	0.004 (2)	0.0020 (18)	0.0089 (19)
C13	0.037 (3)	0.032 (3)	0.061 (4)	−0.005 (3)	−0.009 (3)	0.016 (3)
C14	0.035 (3)	0.034 (3)	0.047 (3)	−0.001 (2)	−0.010 (2)	0.014 (2)
C15	0.042 (3)	0.027 (3)	0.021 (2)	0.008 (2)	0.004 (2)	0.003 (2)
C16	0.040 (4)	0.054 (4)	0.073 (5)	0.016 (3)	0.026 (3)	0.038 (4)
C17	0.038 (3)	0.052 (4)	0.063 (4)	0.020 (3)	0.019 (3)	0.028 (3)

Geometric parameters (Å, º)

Cu1—N3	1.992 (5)	C3—H3A	0.9300
Cu1—O1	2.000 (4)	C4—C12	1.410 (7)
Cu1—N2	2.025 (4)	C4—C5	1.441 (8)
Cu1—N1	2.030 (4)	C5—C6	1.351 (9)
Cu1—O7	2.230 (4)	C5—H5A	0.9300
O1—N4	1.280 (6)	C6—C7	1.430 (8)
O2—N4	1.239 (7)	C6—H6A	0.9300
O3—N4	1.238 (6)	C7—C11	1.406 (7)
O4—N5	1.253 (8)	C7—C8	1.423 (8)
O5—N5	1.220 (8)	C8—C9	1.367 (9)
O6—N5	1.243 (8)	C8—H8	0.9300
O7—H1W	0.8200	C9—C10	1.400 (8)
O7—H2W	0.8251	C9—H9	0.9300
N1—C10	1.341 (7)	C10—H10	0.9300
N1—C11	1.359 (7)	C11—C12	1.429 (7)
N2—C1	1.336 (7)	C13—C14	1.372 (8)
N2—C12	1.355 (7)	C13—H13	0.9300
N3—C13	1.338 (8)	C14—C15	1.387 (9)
N3—C17	1.343 (9)	C14—H14	0.9300
C1—C2	1.386 (8)	C15—C16	1.388 (9)
C1—H1	0.9300	C15—C15^i	1.485 (10)
C2—C3	1.368 (10)	C16—C17	1.376 (9)
C2—H2A	0.9300	C16—H16	0.9300
C3—C4	1.412 (8)	C17—H17	0.9300
N3—Cu1—O1	93.23 (18)	C3—C4—C5	124.7 (5)
N3—Cu1—N2	172.57 (18)	C6—C5—C4	120.5 (5)
O1—Cu1—N2	91.76 (17)	C6—C5—H5A	119.8
N3—Cu1—N1	92.10 (18)	C4—C5—H5A	119.8
O1—Cu1—N1	161.67 (18)	C5—C6—C7	121.9 (5)
N2—Cu1—N1	81.49 (17)	C5—C6—H6A	119.1
N3—Cu1—O7	98.37 (19)	C7—C6—H6A	119.1
O1—Cu1—O7	92.06 (18)	C11—C7—C8	116.8 (5)
N2—Cu1—O7	86.94 (17)	C11—C7—C6	118.8 (5)
N1—Cu1—O7	104.49 (18)	C8—C7—C6	124.3 (5)
N4—O1—Cu1	111.1 (3)	C9—C8—C7	118.9 (5)
Cu1—O7—H1W	109.5	C9—C8—H8	120.5
Cu1—O7—H2W	136.7	C7—C8—H8	120.5
H1W—O7—H2W	113.0	C8—C9—C10	120.6 (5)
C10—N1—C11	118.0 (5)	C8—C9—H9	119.7
C10—N1—Cu1	129.5 (4)	C10—C9—H9	119.7
C11—N1—Cu1	112.5 (3)	N1—C10—C9	121.9 (5)
C1—N2—C12	118.7 (5)	N1—C10—H10	119.0
C1—N2—Cu1	128.6 (4)	C9—C10—H10	119.0
C12—N2—Cu1	112.6 (3)	N1—C11—C7	123.7 (5)
C13—N3—C17	117.3 (5)	N1—C11—C12	116.5 (4)
C13—N3—Cu1	121.4 (4)	C7—C11—C12	119.9 (5)
C17—N3—Cu1	120.7 (4)	N2—C12—C4	123.0 (5)
O3—N4—O2	123.2 (5)	N2—C12—C11	116.9 (4)
O3—N4—O1	118.3 (5)	C4—C12—C11	120.1 (5)
O2—N4—O1	118.5 (4)	N3—C13—C14	123.2 (6)
O5—N5—O6	120.3 (7)	N3—C13—H13	118.4
O5—N5—O4	120.5 (6)	C14—C13—H13	118.4
O6—N5—O4	119.2 (6)	C13—C14—C15	120.3 (6)
N2—C1—C2	122.0 (5)	C13—C14—H14	119.8
N2—C1—H1	119.0	C15—C14—H14	119.8
C2—C1—H1	119.0	C14—C15—C16	116.1 (5)
C3—C2—C1	120.1 (5)	C14—C15—C15^i	121.2 (7)
C3—C2—H2A	119.9	C16—C15—C15^i	122.7 (7)
C1—C2—H2A	119.9	C17—C16—C15	120.8 (6)
C2—C3—C4	119.8 (5)	C17—C16—H16	119.6
C2—C3—H3A	120.1	C15—C16—H16	119.6
C4—C3—H3A	120.1	N3—C17—C16	122.3 (6)
C12—C4—C3	116.5 (5)	N3—C17—H17	118.9
C12—C4—C5	118.8 (5)	C16—C17—H17	118.9
N3—Cu1—O1—N4	97.0 (4)	C5—C6—C7—C11	−0.7 (8)
N2—Cu1—O1—N4	−77.5 (4)	C5—C6—C7—C8	179.6 (5)
N1—Cu1—O1—N4	−9.7 (7)	C11—C7—C8—C9	0.3 (8)
O7—Cu1—O1—N4	−164.5 (4)	C6—C7—C8—C9	−180.0 (5)
N3—Cu1—N1—C10	4.4 (5)	C7—C8—C9—C10	0.2 (9)
O1—Cu1—N1—C10	111.3 (6)	C11—N1—C10—C9	0.6 (8)
N2—Cu1—N1—C10	−179.4 (5)	Cu1—N1—C10—C9	179.8 (4)
O7—Cu1—N1—C10	−94.8 (5)	C8—C9—C10—N1	−0.7 (9)
N3—Cu1—N1—C11	−176.3 (4)	C10—N1—C11—C7	0.1 (8)
O1—Cu1—N1—C11	−69.4 (7)	Cu1—N1—C11—C7	−179.3 (4)
N2—Cu1—N1—C11	−0.1 (3)	C10—N1—C11—C12	179.1 (4)
O7—Cu1—N1—C11	84.5 (4)	Cu1—N1—C11—C12	−0.3 (6)
N3—Cu1—N2—C1	−148.8 (13)	C8—C7—C11—N1	−0.5 (8)
O1—Cu1—N2—C1	−16.6 (5)	C6—C7—C11—N1	179.8 (5)
N1—Cu1—N2—C1	−179.5 (5)	C8—C7—C11—C12	−179.5 (5)
O7—Cu1—N2—C1	75.4 (5)	C6—C7—C11—C12	0.8 (8)
N3—Cu1—N2—C12	31.2 (15)	C1—N2—C12—C4	−0.3 (8)
O1—Cu1—N2—C12	163.4 (4)	Cu1—N2—C12—C4	179.8 (4)
N1—Cu1—N2—C12	0.5 (3)	C1—N2—C12—C11	179.1 (5)
O7—Cu1—N2—C12	−104.6 (4)	Cu1—N2—C12—C11	−0.9 (6)
O1—Cu1—N3—C13	115.9 (5)	C3—C4—C12—N2	−0.3 (8)
N2—Cu1—N3—C13	−112.0 (14)	C5—C4—C12—N2	179.9 (5)
N1—Cu1—N3—C13	−81.6 (5)	C3—C4—C12—C11	−179.7 (5)
O7—Cu1—N3—C13	23.4 (5)	C5—C4—C12—C11	0.5 (8)
O1—Cu1—N3—C17	−73.1 (5)	N1—C11—C12—N2	0.8 (7)
N2—Cu1—N3—C17	59.0 (15)	C7—C11—C12—N2	179.9 (4)
N1—Cu1—N3—C17	89.3 (5)	N1—C11—C12—C4	−179.8 (4)
O7—Cu1—N3—C17	−165.7 (5)	C7—C11—C12—C4	−0.7 (8)
Cu1—O1—N4—O3	172.2 (4)	C17—N3—C13—C14	0.6 (10)
Cu1—O1—N4—O2	−6.7 (6)	Cu1—N3—C13—C14	171.9 (5)
C12—N2—C1—C2	0.5 (8)	N3—C13—C14—C15	0.5 (11)
Cu1—N2—C1—C2	−179.5 (4)	C13—C14—C15—C16	−0.7 (9)
N2—C1—C2—C3	−0.1 (9)	C13—C14—C15—C15^i	−179.6 (7)
C1—C2—C3—C4	−0.5 (9)	C14—C15—C16—C17	−0.1 (10)
C2—C3—C4—C12	0.6 (8)	C15^i—C15—C16—C17	178.7 (7)
C2—C3—C4—C5	−179.5 (5)	C13—N3—C17—C16	−1.5 (11)
C12—C4—C5—C6	−0.4 (8)	Cu1—N3—C17—C16	−172.8 (6)
C3—C4—C5—C6	179.8 (6)	C15—C16—C17—N3	1.3 (12)
C4—C5—C6—C7	0.5 (9)

Symmetry code: (i) −x+1, −y+2, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O7—H2W···O3^ii	0.83	2.07	2.886 (6)	172

Symmetry code: (ii) x−1, y, z.