(Benzoyl­acetonato)­chloro(1,10-phen­anthroline)copper(II)

The crystal structure of the title compound, chloro(1,10-phenanthroline-N,N')(1-phenyl-1,3-butane­dion­ato-O,O')copper(II), [CuCl(C₁₀H₉O₂)(C₁₂H₈N₂)], has been determined. The Cu^II ion displays a distorted square-pyramidal coordination, being linked to the two O atoms of the benzoyl­acetonate ligand and the two N atoms of the 1,10-phenanthroline ligand in the basal plane, and the Cl atom in the apical site. TheCu-N, Cu-O and Cu-Cl bond lengths are 2.043 (2)/2.025 (2), 1.914 (2)/1.941 (2) and 2.485 (1) Å, respectively.

S1. Comment

Interest in mixed-ligand chelate complexes have been clearly established in inorganic and bioinorganic chemistry in the last decade years (Solans et al., 1987, 1993; Moreno-Esparza et al., 1995; Heldal & Sletten, 1997; Gasque et al., 1999; Venkatraman et al., 1999). A series of compounds of formula M(N—N)(O—O) (M = Cu, N—N = o-phenanthroline, O—O = salicylaldehydato, acetylacetonato or benzoylacetonato) have been synthesized and characterized (Solans et al., 1987; Keramidas et al., 1994). The title compound is a member of this series of complexes and its crystal structure is determined in order to obtain the ligand arrangement around the Cu ion.

We have reported previously the structures of several dimeric and monomeric Cu^II complexes (Elmali et al., 1993, 1995, 1997; Elerman et al., 1995; Elerman & Geselle, 1997; Kabak et al., 1999). We report here the crystal structure of (benzoylacetonato)chloro(1,10-phenanthroline)copper(II). \sch

The Cu ion displays a distorted square-pyramidal coordination, being linked to two O atoms of the benzoylacetonato ligand and two N atoms of the 1,10-phenanthroline ligand in the basal plane and the Cl atom in the apical site.

The Cu—N(phenanthroline) distances [2.025 (2)–2.043 (2) Å] are similar, within experimental error, to those reported in several related complexes [mean value 2.019 (7) Å; Solans et al., 1988], [mean value 2.019 (2) Å; Moreno-Esparza et al., 1995], [mean value 2.027 (4) Å; Venkatraman et al., 1999] and while it is shorter than that observed in these complexes [mean value 2.050 (1) Å; Boys, Escobar & Martínez-Carrera, 1981], [mean value 2.099 (4) Å; Heldal & Sletten 1997], it is larger than that reported for other complexes [mean value 2.006 (4) Å; Fabretti et al., 1985], [mean value 1.998 (3) Å; Solans et al., 1987], and [mean value 2.003 (3) Å; Alvarez-Lorena et al., 1995].

The Cu—O distances [1.914 (2)–1.941 (2) Å] are similar, within experimental error, to those reported in the related complexes [mean value 1.925 (3) Å; Solans et al., 1987], [mean value 1.925 (1) Å; Gasque et al., 1999], but it is shorter than that observed in this complex [mean value 1.986 (5) Å; Heldal & Sletten, 1997].

The π-bond character of the C14—O2 bond produces a lengthening of the Cu—O2 bond distance, 1.941 (2) Å, with respect to 1.914 (2) Å observed for Cu—O1. This effect is also observed in (1,10-phenanthroline)(salicylaldehydato)copper(II)nitrate (Solans et al., 1987) where these distances are 1.952 (3) and 1.898 (3) Å, respectively. This fact explains the shortening of the Cu—N2 bond distance [2.025 (2) Å, trans to O1] with respect to 2.043 (2) Å observed for Cu—N1 [trans to O2].

The Cl atom lies above the plane, at the apex of the slight distorted pyramid. The Cu—Cl (apical) bond length [2.485 (1) Å] is intermediate when compared with the following values: [2.192 (1) Å; Chiari et al., 1987], [2.233 (1) Å; Mégnamisi-Bélombé & Endres, 1983], [2.463 (1) Å; Nicholson et al., 1982], [2.546 (2) Å; Solans et al., 1988], [2.560 (1) Å; Thompson et al., 1996], [2.734 (4) Å; Phelps et al., 1976].

Mean planes in the molecule are the five-membered phenanthroline chelate ring defined by atoms N1, C5, C9, N2 and Cu1, which is planar with negligible distortion (avarage r.m.s. deviation from the five-atom plane is 0.0199 Å), and the plane defined by atoms O1, C16, C14, O2 and Cu1, which is roughly planar (average r.m.s. deviation from the five-atom plane is 0.0246 Å). The angle between the phenanthroline chelate plane (N1, C5, C9, N2 and Cu1) and the benzoylacetonato moiety excluding the C15 atom (O1, C14, C16, O2 and Cu1) is 23.37 (6)°. The angle between the planes of coordination-plane atoms and the phenanthroline molecule is 7.77 (8)° and that formed with the benzoylacetonato moiety is 16.92 (7)°. The Cu atom is displaced by 0.28 (1) Å, out of the least square plane containing O1, O2, N1, N2 toward the apical positions.

S2. Experimental

The complex was prepared by mixing copper(II)chloride dihydrate, 1,10-phenanthroline and benzoylacetone in the ratio 1:1:1 in ethanol. The solutions were allowed to stand for several days and green crystals precipitated.

Computing details

Data collection: CAD-4 Diffractometer Control Software (Nonius, 1993); cell refinement: CAD-4 Diffractometer Control Software; data reduction: REDU4 (Stoe & Cie, 1991); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-III (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Figures

Fig. 1. The molecular structure of the title compound showing the atom-labelling scheme and 50% probability level displacement ellipsoids for the non-H atoms. H atoms are drawn as spheres of arbitrary radii (ORTEP-3; Farrugia, 1997).

(I)

Crystal data

[CuCl(C10H9O2)(C12H8N2)]	F(000) = 1808
Mr = 441.37	Dx = 1.542 Mg m^−3
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54180 Å
a = 14.453 (3) Å	Cell parameters from 25 reflections
b = 10.3993 (13) Å	θ = 22.6–42.4°
c = 25.371 (2) Å	µ = 3.08 mm^−1
β = 94.366 (1)°	T = 293 K
V = 3802.2 (9) Å^3	Plate, green
Z = 8	0.60 × 0.48 × 0.12 mm

Data collection

Enraf-Nonius CAD-4 diffractometer	3485 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.000
Graphite monochromator	θmax = 74.2°, θmin = 3.5°
ω/2θ scans	h = 0→18
Absorption correction: emprical psi scans (north et al., 1968) ?	k = 0→12
Tmin = 0.216, Tmax = 0.691	l = −31→31
3860 measured reflections	3 standard reflections every 120 min
3860 independent reflections	intensity decay: −1.4%

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.157	H-atom parameters constrained
S = 1.06	Calculated w = 1/[σ^2(Fo^2) + (0.0991P)^2 + 4.6891P] where P = (Fo^2 + 2Fc^2)/3
3860 reflections	(Δ/σ)max = 0.001
253 parameters	Δρmax = 0.57 e Å^−3
0 restraints	Δρmin = −0.65 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.

The structure was solved by direct-phase determination. The parameters of the complete structure could be refined by full-matrix anisotropic least squares. All phenyl rings were refined without any constraints. Values of distances and angles in the rings show no significant differences from those of an ideal benzene ring. All hydrogen positions were calculated using a riding model and were considered with fixed isotropic U's in all refinements. It was possible to refine the parameters of the complete structure by full-matrix anisotropic least squares.

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

	x	y	z	Uiso*/Ueq
Cu1	0.88365 (3)	0.14853 (4)	0.409918 (15)	0.04639 (18)
Cl1	0.83749 (5)	0.37300 (8)	0.38689 (3)	0.0558 (2)
O1	0.91450 (14)	0.1707 (2)	0.48406 (8)	0.0531 (5)
O2	1.01221 (15)	0.1498 (2)	0.39264 (9)	0.0558 (5)
N1	0.75719 (15)	0.0746 (2)	0.42452 (9)	0.0447 (5)
N2	0.84404 (18)	0.0827 (3)	0.33656 (10)	0.0546 (6)
C1	0.7156 (2)	0.0723 (3)	0.46952 (11)	0.0501 (6)
H1	0.7466	0.1055	0.5000	0.060*
C2	0.6268 (2)	0.0217 (3)	0.47238 (13)	0.0564 (7)
H2	0.5999	0.0201	0.5045	0.068*
C3	0.5791 (2)	−0.0257 (3)	0.42788 (13)	0.0570 (7)
H3	0.5197	−0.0592	0.4296	0.068*
C4	0.6204 (2)	−0.0232 (3)	0.38005 (12)	0.0523 (7)
C5	0.71048 (19)	0.0279 (3)	0.38050 (11)	0.0460 (6)
C6	0.5777 (2)	−0.0690 (4)	0.33092 (14)	0.0658 (9)
H6	0.5181	−0.1029	0.3300	0.079*
C7	0.6218 (3)	−0.0644 (4)	0.28569 (14)	0.0721 (10)
H7	0.5921	−0.0955	0.2545	0.087*
C8	0.7141 (2)	−0.0122 (4)	0.28521 (13)	0.0608 (8)
C9	0.7575 (2)	0.0330 (3)	0.33299 (11)	0.0508 (6)
C10	0.7643 (3)	−0.0047 (5)	0.24014 (13)	0.0767 (11)
H10	0.7385	−0.0340	0.2076	0.092*
C11	0.8516 (3)	0.0463 (5)	0.24476 (14)	0.0829 (13)
H11	0.8858	0.0519	0.2152	0.100*
C12	0.8894 (3)	0.0898 (4)	0.29335 (13)	0.0706 (10)
H12	0.9486	0.1253	0.2956	0.085*
C13	1.1752 (2)	0.1452 (4)	0.40487 (17)	0.0711 (10)
H13A	1.1678	0.1382	0.3671	0.085*
H13B	1.2083	0.0715	0.4192	0.085*
H13C	1.2096	0.2217	0.4145	0.085*
C14	1.0815 (2)	0.1516 (3)	0.42653 (14)	0.0529 (7)
C15	1.0770 (2)	0.1615 (3)	0.48075 (14)	0.0576 (8)
H15	1.1329	0.1594	0.5015	0.069*
C16	0.9961 (2)	0.1744 (3)	0.50701 (12)	0.0473 (6)
C17	1.0009 (2)	0.1936 (3)	0.56522 (12)	0.0550 (7)
C18	0.9219 (3)	0.1777 (4)	0.59251 (13)	0.0613 (8)
H18	0.8666	0.1520	0.5744	0.074*
C19	0.9246 (3)	0.1996 (5)	0.64590 (15)	0.0813 (11)
H19	0.8717	0.1878	0.6640	0.098*
C20	1.0069 (4)	0.2394 (6)	0.67267 (16)	0.1059 (18)
H20	1.0091	0.2546	0.7089	0.127*
C21	1.0837 (4)	0.2562 (7)	0.64648 (19)	0.119 (2)
H21	1.1386	0.2828	0.6647	0.143*
C22	1.0815 (3)	0.2344 (6)	0.59332 (16)	0.0910 (15)
H22	1.1349	0.2472	0.5757	0.109*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0381 (3)	0.0607 (3)	0.0403 (3)	−0.00577 (16)	0.00221 (17)	−0.00516 (16)
Cl1	0.0532 (4)	0.0611 (4)	0.0524 (4)	0.0011 (3)	−0.0005 (3)	0.0046 (3)
O1	0.0411 (10)	0.0709 (13)	0.0466 (11)	−0.0053 (9)	−0.0010 (8)	0.0023 (9)
O2	0.0425 (10)	0.0700 (14)	0.0554 (12)	−0.0002 (9)	0.0069 (9)	−0.0027 (10)
N1	0.0432 (11)	0.0528 (13)	0.0380 (11)	−0.0048 (10)	0.0025 (9)	−0.0042 (9)
N2	0.0494 (13)	0.0703 (16)	0.0445 (13)	−0.0089 (12)	0.0057 (10)	−0.0092 (12)
C1	0.0514 (15)	0.0596 (17)	0.0393 (13)	−0.0049 (13)	0.0040 (11)	−0.0032 (12)
C2	0.0522 (16)	0.0659 (18)	0.0525 (16)	−0.0069 (14)	0.0125 (13)	−0.0021 (14)
C3	0.0438 (15)	0.0617 (18)	0.0657 (19)	−0.0096 (13)	0.0064 (13)	−0.0022 (15)
C4	0.0464 (15)	0.0573 (16)	0.0525 (16)	−0.0059 (12)	−0.0007 (12)	−0.0038 (13)
C5	0.0436 (14)	0.0504 (14)	0.0435 (14)	−0.0050 (11)	0.0009 (11)	−0.0028 (11)
C6	0.0534 (17)	0.082 (2)	0.0614 (19)	−0.0171 (16)	−0.0037 (14)	−0.0110 (17)
C7	0.068 (2)	0.091 (3)	0.0555 (19)	−0.0164 (19)	−0.0086 (16)	−0.0176 (18)
C8	0.0630 (19)	0.074 (2)	0.0448 (15)	−0.0072 (16)	0.0016 (13)	−0.0127 (15)
C9	0.0499 (15)	0.0587 (16)	0.0436 (14)	−0.0051 (13)	0.0033 (11)	−0.0078 (12)
C10	0.081 (2)	0.106 (3)	0.0431 (17)	−0.011 (2)	0.0017 (15)	−0.0217 (18)
C11	0.080 (3)	0.123 (4)	0.0481 (18)	−0.018 (2)	0.0209 (17)	−0.019 (2)
C12	0.063 (2)	0.101 (3)	0.0501 (17)	−0.0160 (19)	0.0177 (15)	−0.0179 (18)
C13	0.0428 (17)	0.085 (3)	0.086 (3)	0.0045 (15)	0.0092 (16)	−0.004 (2)
C14	0.0414 (15)	0.0519 (16)	0.0657 (19)	0.0005 (11)	0.0058 (13)	−0.0014 (13)
C15	0.0370 (14)	0.0671 (19)	0.0670 (19)	0.0008 (12)	−0.0079 (13)	0.0009 (15)
C16	0.0430 (14)	0.0484 (14)	0.0494 (15)	−0.0047 (11)	−0.0038 (11)	0.0051 (12)
C17	0.0574 (17)	0.0584 (17)	0.0475 (15)	−0.0068 (14)	−0.0081 (13)	0.0084 (13)
C18	0.068 (2)	0.0639 (19)	0.0507 (17)	−0.0066 (16)	−0.0011 (14)	0.0106 (14)
C19	0.102 (3)	0.089 (3)	0.054 (2)	−0.002 (2)	0.012 (2)	0.0123 (19)
C20	0.138 (5)	0.138 (5)	0.0392 (18)	−0.003 (4)	−0.008 (2)	0.003 (2)
C21	0.102 (4)	0.191 (7)	0.058 (2)	−0.021 (4)	−0.029 (3)	−0.014 (3)
C22	0.068 (2)	0.141 (4)	0.061 (2)	−0.024 (3)	−0.0142 (18)	−0.005 (2)

Geometric parameters (Å, º)

Cu1—O1	1.914 (2)	C8—C9	1.403 (4)
Cu1—O2	1.941 (2)	C10—C11	1.366 (6)
Cu1—N2	2.025 (2)	C10—H10	0.9300
Cu1—N1	2.043 (2)	C11—C12	1.386 (5)
Cu1—Cl1	2.4852 (9)	C11—H11	0.9300
O1—C16	1.276 (3)	C12—H12	0.9300
O2—C14	1.269 (4)	C13—C14	1.503 (4)
N1—C1	1.331 (3)	C13—H13A	0.9600
N1—C5	1.351 (3)	C13—H13B	0.9600
N2—C12	1.321 (4)	C13—H13C	0.9600
N2—C9	1.349 (4)	C14—C15	1.386 (5)
C1—C2	1.394 (4)	C15—C16	1.395 (4)
C1—H1	0.9300	C15—H15	0.9300
C2—C3	1.369 (4)	C16—C17	1.487 (4)
C2—H2	0.9300	C17—C22	1.385 (5)
C3—C4	1.393 (4)	C17—C18	1.390 (5)
C3—H3	0.9300	C18—C19	1.371 (5)
C4—C5	1.406 (4)	C18—H18	0.9300
C4—C6	1.429 (4)	C19—C20	1.387 (7)
C5—C9	1.430 (4)	C19—H19	0.9300
C6—C7	1.355 (5)	C20—C21	1.348 (8)
C6—H6	0.9300	C20—H20	0.9300
C7—C8	1.441 (5)	C21—C22	1.365 (6)
C7—H7	0.9300	C21—H21	0.9300
C8—C10	1.402 (5)	C22—H22	0.9300
O1—Cu1—O2	93.77 (9)	C8—C9—C5	120.4 (3)
O1—Cu1—N2	166.60 (11)	C11—C10—C8	118.9 (3)
O2—Cu1—N2	90.19 (10)	C11—C10—H10	120.6
O1—Cu1—N1	90.67 (9)	C8—C10—H10	120.6
O2—Cu1—N1	158.21 (10)	C10—C11—C12	120.2 (3)
N2—Cu1—N1	81.09 (9)	C10—C11—H11	119.9
O1—Cu1—Cl1	98.99 (7)	C12—C11—H11	119.9
O2—Cu1—Cl1	100.66 (7)	N2—C12—C11	122.2 (3)
N2—Cu1—Cl1	92.84 (9)	N2—C12—H12	118.9
N1—Cu1—Cl1	99.69 (7)	C11—C12—H12	118.9
C16—O1—Cu1	126.2 (2)	C14—C13—H13A	109.5
C14—O2—Cu1	124.5 (2)	C14—C13—H13B	109.5
C1—N1—C5	118.2 (2)	H13A—C13—H13B	109.5
C1—N1—Cu1	129.18 (19)	C14—C13—H13C	109.5
C5—N1—Cu1	112.53 (18)	H13A—C13—H13C	109.5
C12—N2—C9	118.8 (3)	H13B—C13—H13C	109.5
C12—N2—Cu1	128.3 (2)	O2—C14—C15	125.4 (3)
C9—N2—Cu1	112.77 (19)	O2—C14—C13	116.0 (3)
N1—C1—C2	122.0 (3)	C15—C14—C13	118.6 (3)
N1—C1—H1	119.0	C14—C15—C16	125.8 (3)
C2—C1—H1	119.0	C14—C15—H15	117.1
C3—C2—C1	120.1 (3)	C16—C15—H15	117.1
C3—C2—H2	120.0	O1—C16—C15	123.9 (3)
C1—C2—H2	120.0	O1—C16—C17	115.4 (3)
C2—C3—C4	119.3 (3)	C15—C16—C17	120.7 (3)
C2—C3—H3	120.3	C22—C17—C18	118.1 (3)
C4—C3—H3	120.3	C22—C17—C16	121.7 (3)
C3—C4—C5	117.3 (3)	C18—C17—C16	120.1 (3)
C3—C4—C6	124.7 (3)	C19—C18—C17	120.6 (4)
C5—C4—C6	118.1 (3)	C19—C18—H18	119.7
N1—C5—C4	123.2 (3)	C17—C18—H18	119.7
N1—C5—C9	116.4 (2)	C18—C19—C20	119.5 (4)
C4—C5—C9	120.5 (3)	C18—C19—H19	120.3
C7—C6—C4	121.8 (3)	C20—C19—H19	120.3
C7—C6—H6	119.1	C21—C20—C19	120.3 (4)
C4—C6—H6	119.1	C21—C20—H20	119.8
C6—C7—C8	121.0 (3)	C19—C20—H20	119.8
C6—C7—H7	119.5	C20—C21—C22	120.5 (5)
C8—C7—H7	119.5	C20—C21—H21	119.8
C10—C8—C9	117.5 (3)	C22—C21—H21	119.8
C10—C8—C7	124.3 (3)	C21—C22—C17	121.0 (5)
C9—C8—C7	118.2 (3)	C21—C22—H22	119.5
N2—C9—C8	122.5 (3)	C17—C22—H22	119.5
N2—C9—C5	117.1 (3)
O2—Cu1—O1—C16	−3.8 (3)	C6—C7—C8—C10	179.7 (4)
N2—Cu1—O1—C16	103.1 (4)	C6—C7—C8—C9	0.5 (6)
N1—Cu1—O1—C16	154.9 (2)	C12—N2—C9—C8	0.4 (5)
Cl1—Cu1—O1—C16	−105.2 (2)	Cu1—N2—C9—C8	176.6 (3)
O1—Cu1—O2—C14	6.2 (3)	C12—N2—C9—C5	−179.5 (3)
N2—Cu1—O2—C14	−161.0 (3)	Cu1—N2—C9—C5	−3.3 (4)
N1—Cu1—O2—C14	−95.1 (3)	C10—C8—C9—N2	0.3 (6)
Cl1—Cu1—O2—C14	106.1 (2)	C7—C8—C9—N2	179.5 (3)
O1—Cu1—N1—C1	10.6 (3)	C10—C8—C9—C5	−179.8 (3)
O2—Cu1—N1—C1	112.6 (3)	C7—C8—C9—C5	−0.5 (5)
N2—Cu1—N1—C1	−180.0 (3)	N1—C5—C9—N2	0.5 (4)
Cl1—Cu1—N1—C1	−88.6 (3)	C4—C5—C9—N2	−179.7 (3)
O1—Cu1—N1—C5	−172.6 (2)	N1—C5—C9—C8	−179.4 (3)
O2—Cu1—N1—C5	−70.7 (3)	C4—C5—C9—C8	0.4 (5)
N2—Cu1—N1—C5	−3.2 (2)	C9—C8—C10—C11	−0.5 (6)
Cl1—Cu1—N1—C5	88.2 (2)	C7—C8—C10—C11	−179.7 (5)
O1—Cu1—N2—C12	−128.1 (4)	C8—C10—C11—C12	0.0 (7)
O2—Cu1—N2—C12	−20.8 (4)	C9—N2—C12—C11	−1.0 (6)
N1—Cu1—N2—C12	179.3 (4)	Cu1—N2—C12—C11	−176.5 (4)
Cl1—Cu1—N2—C12	79.9 (3)	C10—C11—C12—N2	0.8 (8)
O1—Cu1—N2—C9	56.1 (5)	Cu1—O2—C14—C15	−4.5 (4)
O2—Cu1—N2—C9	163.5 (2)	Cu1—O2—C14—C13	176.9 (2)
N1—Cu1—N2—C9	3.5 (2)	O2—C14—C15—C16	−1.7 (5)
Cl1—Cu1—N2—C9	−95.9 (2)	C13—C14—C15—C16	176.9 (3)
C5—N1—C1—C2	1.0 (4)	Cu1—O1—C16—C15	−0.5 (4)
Cu1—N1—C1—C2	177.6 (2)	Cu1—O1—C16—C17	179.6 (2)
N1—C1—C2—C3	−1.1 (5)	C14—C15—C16—O1	4.5 (5)
C1—C2—C3—C4	0.3 (5)	C14—C15—C16—C17	−175.5 (3)
C2—C3—C4—C5	0.5 (5)	O1—C16—C17—C22	−162.0 (4)
C2—C3—C4—C6	−179.7 (3)	C15—C16—C17—C22	18.1 (5)
C1—N1—C5—C4	−0.2 (4)	O1—C16—C17—C18	14.3 (4)
Cu1—N1—C5—C4	−177.3 (2)	C15—C16—C17—C18	−165.6 (3)
C1—N1—C5—C9	179.6 (3)	C22—C17—C18—C19	−1.2 (6)
Cu1—N1—C5—C9	2.5 (3)	C16—C17—C18—C19	−177.7 (3)
C3—C4—C5—N1	−0.6 (5)	C17—C18—C19—C20	0.8 (7)
C6—C4—C5—N1	179.6 (3)	C18—C19—C20—C21	−0.2 (9)
C3—C4—C5—C9	179.7 (3)	C19—C20—C21—C22	0.1 (10)
C6—C4—C5—C9	−0.2 (5)	C20—C21—C22—C17	−0.6 (10)
C3—C4—C6—C7	−179.7 (4)	C18—C17—C22—C21	1.2 (8)
C5—C4—C6—C7	0.1 (6)	C16—C17—C22—C21	177.5 (5)
C4—C6—C7—C8	−0.3 (6)