Bis[2,3,4-trimethyl-5-[(3,4,5-trimethyl-2H-pyrrol-2-yl-idene-κN)meth-yl]-1H-pyrrolato-κN]copper(II).

In the title complex, [Cu(C(15)H(19)N(2))(2)] or [Cu(L(2))] (HL is 3,3',4,4',5,5'-hexa-methyl-pyrromethene), the Cu(II) atom is coordinated by four N atoms [Cu-N 1.939 (2)-1.976 (2) Å] from two L ligands in a distorted tetra-hedral geometry. The mean planes of the CuN(2)C(3) metallocyclic rings form a dihedral angle of 72.73 (6)°. In the L ligands, the pyrrole rings are inclined to each other at dihedral angles of 3.03 (7) and 9.83 (7)°. The crystal packing exhibits weak inter-molecular C-H⋯π inter-actions, which form chains in [100].

Related literature

For the structure of the neutral ligand, see: Mroginski et al. (2005 ▶). For the structures of related organometallic complexes, see: Elder & Penfold (1969 ▶); Cotton et al. (1970 ▶); Fergusson et al. (1971 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶). For transition metal complexes of dipyrromethenes, see: Bruckner et al. (1997 ▶); Zhang et al. (1998 ▶). For the chemistry and applications of pyrrole derivatives, see: Dolphin (1979 ▶); Falk (1989 ▶). For the synthesis of the title compound, see: Murakami & Sakata (1968 ▶). For IDEAL software, see: Gould et al. (1988 ▶).

Experimental

Crystal data

[Cu(C15H19N2)2]

M = 518.18

Triclinic,

a = 7.9737 (1) Å

b = 12.0896 (3) Å

c = 13.9411 (4) Å

α = 92.8065 (8)°

β = 105.4205 (8)°

γ = 91.9772 (18)°

V = 1292.39 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.87 mm−1

T = 120 K

0.18 × 0.10 × 0.02 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (HKL SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.859, T max = 0.983

20968 measured reflections

7342 independent reflections

5581 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.117

S = 1.02

7342 reflections

328 parameters

H-atom parameters constrained

Δρmax = 0.49 e Å−3

Δρmin = −0.48 e Å−3

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812040998/cv5335sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812040998/cv5335Isup2.hkl

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

[Cu(C15H19N2)2]	Z = 2
Mr = 518.18	F(000) = 550
Triclinic, P1	Dx = 1.331 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9737 (1) Å	Cell parameters from 6313 reflections
b = 12.0896 (3) Å	θ = 2.5–30°
c = 13.9411 (4) Å	µ = 0.87 mm−1
α = 92.8065 (8)°	T = 120 K
β = 105.4205 (8)°	Lath fragment, metallic green
γ = 91.9772 (18)°	0.18 × 0.10 × 0.02 mm
V = 1292.39 (5) Å3

Nonius KappaCCD diffractometer	7342 independent reflections
Radiation source: sealed tube	5581 reflections with I > 2σ(I)
Horizonally mounted graphite crystal monochromator	Rint = 0.052
Detector resolution: 9 pixels mm-1	θmax = 30.0°, θmin = 2.6°
φ and ω scans	h = −11→10
Absorption correction: multi-scan (HKLSCALEPACK; Otwinowski & Minor, 1997)	k = −17→16
Tmin = 0.859, Tmax = 0.983	l = 0→19
20968 measured reflections

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0459P)2 + 1.301P] where P = (Fo2 + 2Fc2)/3
7342 reflections	(Δ/σ)max = 0.001
328 parameters	Δρmax = 0.49 e Å−3
0 restraints	Δρmin = −0.48 e Å−3
0 constraints

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.

	x	y	z	Uiso*/Ueq
C1	0.0551 (3)	0.30099 (19)	0.06874 (18)	0.0170 (4)
C2	0.1508 (3)	0.3865 (2)	0.03636 (18)	0.0182 (5)
C3	0.2301 (3)	0.45455 (19)	0.11937 (18)	0.0177 (5)
C4	0.1808 (3)	0.41018 (18)	0.20159 (18)	0.0163 (4)
C5	0.2270 (3)	0.45235 (19)	0.30043 (18)	0.0166 (4)
H5	0.293	0.521	0.313	0.02*
C6	0.1901 (3)	0.40808 (18)	0.38310 (18)	0.0161 (4)
C7	0.2300 (3)	0.45367 (19)	0.48376 (18)	0.0182 (5)
C8	0.1726 (3)	0.3752 (2)	0.53829 (18)	0.0180 (5)
C9	0.0982 (3)	0.28389 (19)	0.47050 (18)	0.0167 (4)
C10	−0.0506 (3)	0.2066 (2)	0.00526 (19)	0.0228 (5)
H10A	−0.0581	0.1444	0.0467	0.034*
H10B	0.005	0.1832	−0.0467	0.034*
H10C	−0.168	0.2302	−0.0259	0.034*
C11	0.1629 (3)	0.3977 (2)	−0.06840 (19)	0.0246 (5)
H11A	0.1608	0.4762	−0.0831	0.037*
H11B	0.064	0.3566	−0.115	0.037*
H11C	0.2719	0.3677	−0.0755	0.037*
C12	0.3503 (4)	0.5533 (2)	0.1225 (2)	0.0278 (6)
H12A	0.4591	0.5289	0.1102	0.042*
H12B	0.3756	0.5928	0.1882	0.042*
H12C	0.295	0.603	0.0711	0.042*
C13	0.3121 (3)	0.5663 (2)	0.5217 (2)	0.0239 (5)
H13A	0.221	0.6179	0.5241	0.036*
H13B	0.3791	0.5927	0.477	0.036*
H13C	0.39	0.5619	0.5887	0.036*
C14	0.1815 (3)	0.3850 (2)	0.64745 (19)	0.0273 (6)
H14A	0.2834	0.4324	0.683	0.041*
H14B	0.1911	0.3113	0.674	0.041*
H14C	0.0756	0.4179	0.6565	0.041*
C15	0.0127 (3)	0.1785 (2)	0.49176 (19)	0.0206 (5)
H15A	−0.1134	0.1864	0.4772	0.031*
H15B	0.0591	0.1637	0.5621	0.031*
H15C	0.0365	0.1169	0.4498	0.031*
C16	0.3462 (3)	0.07330 (19)	0.34173 (17)	0.0149 (4)
C17	0.4012 (3)	−0.03756 (19)	0.35150 (16)	0.0155 (4)
C18	0.2537 (3)	−0.10652 (19)	0.31410 (17)	0.0152 (4)
C19	0.1112 (3)	−0.03552 (18)	0.28089 (16)	0.0133 (4)
C20	−0.0604 (3)	−0.06651 (18)	0.23318 (16)	0.0146 (4)
H20	−0.0881	−0.1441	0.225	0.018*
C21	−0.1988 (3)	0.00086 (18)	0.19539 (17)	0.0150 (4)
C22	−0.3776 (3)	−0.03267 (19)	0.15404 (17)	0.0161 (4)
C23	−0.4672 (3)	0.0633 (2)	0.13321 (17)	0.0169 (4)
C24	−0.3418 (3)	0.15334 (19)	0.16063 (17)	0.0169 (4)
C25	0.4632 (3)	0.1757 (2)	0.37120 (19)	0.0205 (5)
H25A	0.4076	0.2376	0.3343	0.031*
H25B	0.5741	0.1632	0.3557	0.031*
H25C	0.4844	0.1934	0.4429	0.031*
C26	0.5858 (3)	−0.0683 (2)	0.39435 (18)	0.0202 (5)
H26A	0.5903	−0.1491	0.3948	0.03*
H26B	0.6288	−0.0357	0.4627	0.03*
H26C	0.6588	−0.04	0.3536	0.03*
C27	0.2415 (3)	−0.23026 (19)	0.3073 (2)	0.0211 (5)
H27A	0.3589	−0.2584	0.3252	0.032*
H27B	0.1806	−0.257	0.239	0.032*
H27C	0.1769	−0.2566	0.3532	0.032*
C28	−0.4551 (3)	−0.1488 (2)	0.13782 (19)	0.0221 (5)
H28A	−0.5556	−0.1535	0.1656	0.033*
H28B	−0.3677	−0.1995	0.171	0.033*
H28C	−0.4927	−0.1695	0.0662	0.033*
C29	−0.6605 (3)	0.0712 (2)	0.09145 (19)	0.0234 (5)
H29A	−0.6925	0.0522	0.0195	0.035*
H29B	−0.693	0.147	0.1037	0.035*
H29C	−0.7221	0.0196	0.1239	0.035*
C30	−0.3737 (3)	0.2739 (2)	0.1535 (2)	0.0235 (5)
H30A	−0.3121	0.314	0.2165	0.035*
H30B	−0.4989	0.2846	0.1402	0.035*
H30C	−0.331	0.3023	0.0993	0.035*
N1	0.0723 (2)	0.31450 (16)	0.16751 (15)	0.0158 (4)
N2	0.1078 (2)	0.30305 (15)	0.37825 (14)	0.0150 (4)
N3	0.1743 (2)	0.07482 (15)	0.30066 (14)	0.0141 (4)
N4	−0.1810 (2)	0.11631 (16)	0.19835 (15)	0.0154 (4)
Cu1	0.03402 (3)	0.20344 (2)	0.25992 (2)	0.01496 (9)

	U11	U22	U33	U12	U13	U23
C1	0.0148 (10)	0.0179 (11)	0.0179 (11)	0.0046 (8)	0.0028 (8)	0.0022 (9)
C2	0.0173 (11)	0.0181 (11)	0.0208 (12)	0.0059 (8)	0.0071 (9)	0.0030 (9)
C3	0.0178 (11)	0.0155 (11)	0.0209 (12)	0.0026 (8)	0.0063 (9)	0.0036 (9)
C4	0.0165 (11)	0.0118 (10)	0.0217 (12)	0.0026 (8)	0.0064 (8)	0.0034 (9)
C5	0.0148 (10)	0.0116 (10)	0.0223 (12)	0.0016 (8)	0.0028 (8)	0.0012 (9)
C6	0.0146 (10)	0.0118 (10)	0.0202 (12)	0.0015 (8)	0.0019 (8)	0.0008 (9)
C7	0.0151 (11)	0.0169 (11)	0.0208 (12)	0.0030 (8)	0.0018 (8)	−0.0012 (9)
C8	0.0159 (11)	0.0203 (12)	0.0166 (11)	0.0027 (8)	0.0026 (8)	−0.0009 (9)
C9	0.0126 (10)	0.0179 (11)	0.0193 (12)	0.0041 (8)	0.0027 (8)	0.0033 (9)
C10	0.0208 (12)	0.0254 (13)	0.0203 (13)	−0.0014 (9)	0.0030 (9)	−0.0015 (10)
C11	0.0264 (13)	0.0280 (14)	0.0229 (13)	0.0025 (10)	0.0117 (10)	0.0067 (11)
C12	0.0325 (14)	0.0204 (13)	0.0333 (15)	−0.0065 (10)	0.0147 (11)	0.0030 (11)
C13	0.0266 (13)	0.0182 (12)	0.0233 (13)	−0.0004 (9)	0.0016 (10)	−0.0059 (10)
C14	0.0287 (14)	0.0321 (15)	0.0194 (13)	−0.0012 (11)	0.0044 (10)	−0.0015 (11)
C15	0.0218 (12)	0.0202 (12)	0.0211 (12)	0.0001 (9)	0.0080 (9)	0.0025 (10)
C16	0.0157 (10)	0.0170 (11)	0.0126 (10)	0.0000 (8)	0.0053 (8)	−0.0003 (8)
C17	0.0187 (11)	0.0186 (11)	0.0104 (10)	0.0029 (8)	0.0057 (8)	0.0017 (8)
C18	0.0193 (11)	0.0141 (10)	0.0132 (11)	0.0019 (8)	0.0058 (8)	0.0016 (8)
C19	0.0150 (10)	0.0126 (10)	0.0126 (10)	0.0011 (8)	0.0042 (8)	0.0015 (8)
C20	0.0193 (11)	0.0133 (10)	0.0131 (10)	−0.0014 (8)	0.0080 (8)	0.0003 (8)
C21	0.0173 (11)	0.0150 (11)	0.0128 (11)	−0.0013 (8)	0.0044 (8)	0.0005 (8)
C22	0.0165 (11)	0.0197 (11)	0.0126 (11)	−0.0027 (8)	0.0057 (8)	−0.0017 (9)
C23	0.0139 (11)	0.0246 (12)	0.0120 (11)	0.0003 (8)	0.0034 (8)	−0.0001 (9)
C24	0.0172 (11)	0.0191 (11)	0.0146 (11)	0.0030 (8)	0.0042 (8)	0.0014 (9)
C25	0.0164 (11)	0.0206 (12)	0.0235 (13)	−0.0031 (9)	0.0048 (9)	−0.0015 (10)
C26	0.0183 (11)	0.0258 (13)	0.0166 (12)	0.0058 (9)	0.0039 (9)	0.0028 (10)
C27	0.0240 (12)	0.0149 (11)	0.0262 (13)	0.0051 (9)	0.0091 (10)	0.0028 (10)
C28	0.0174 (11)	0.0235 (13)	0.0235 (13)	−0.0063 (9)	0.0037 (9)	−0.0030 (10)
C29	0.0168 (12)	0.0332 (14)	0.0200 (12)	0.0023 (10)	0.0046 (9)	0.0010 (11)
C30	0.0227 (12)	0.0205 (12)	0.0270 (14)	0.0047 (9)	0.0054 (10)	0.0030 (10)
N1	0.0166 (9)	0.0128 (9)	0.0174 (10)	0.0012 (7)	0.0032 (7)	0.0025 (7)
N2	0.0142 (9)	0.0142 (9)	0.0155 (10)	0.0008 (7)	0.0024 (7)	0.0001 (7)
N3	0.0151 (9)	0.0130 (9)	0.0145 (9)	0.0002 (7)	0.0045 (7)	0.0005 (7)
N4	0.0144 (9)	0.0139 (9)	0.0175 (10)	0.0009 (7)	0.0035 (7)	0.0018 (7)
Cu1	0.01634 (14)	0.01081 (13)	0.01597 (15)	−0.00039 (9)	0.00133 (10)	0.00120 (10)

C1—N1	1.348 (3)	C16—C25	1.496 (3)
C1—C2	1.425 (3)	C17—C18	1.384 (3)
C1—C10	1.495 (3)	C17—C26	1.501 (3)
C2—C3	1.378 (3)	C18—C19	1.438 (3)
C2—C11	1.501 (4)	C18—C27	1.493 (3)
C3—C4	1.429 (3)	C19—C20	1.383 (3)
C3—C12	1.497 (3)	C19—N3	1.397 (3)
C4—C5	1.394 (3)	C20—C21	1.397 (3)
C4—N1	1.404 (3)	C20—H20	0.95
C5—C6	1.390 (3)	C21—N4	1.395 (3)
C5—H5	0.95	C21—C22	1.425 (3)
C6—N2	1.399 (3)	C22—C23	1.386 (3)
C6—C7	1.431 (3)	C22—C28	1.496 (3)
C7—C8	1.384 (3)	C23—C24	1.418 (3)
C7—C13	1.499 (3)	C23—C29	1.504 (3)
C8—C9	1.420 (3)	C24—N4	1.351 (3)
C8—C14	1.503 (4)	C24—C30	1.492 (3)
C9—N2	1.339 (3)	C25—H25A	0.98
C9—C15	1.503 (3)	C25—H25B	0.98
C10—H10A	0.98	C25—H25C	0.98
C10—H10B	0.98	C26—H26A	0.98
C10—H10C	0.98	C26—H26B	0.98
C11—H11A	0.98	C26—H26C	0.98
C11—H11B	0.98	C27—H27A	0.98
C11—H11C	0.98	C27—H27B	0.98
C12—H12A	0.98	C27—H27C	0.98
C12—H12B	0.98	C28—H28A	0.98
C12—H12C	0.98	C28—H28B	0.98
C13—H13A	0.98	C28—H28C	0.98
C13—H13B	0.98	C29—H29A	0.98
C13—H13C	0.98	C29—H29B	0.98
C14—H14A	0.98	C29—H29C	0.98
C14—H14B	0.98	C30—H30A	0.98
C14—H14C	0.98	C30—H30B	0.98
C15—H15A	0.98	C30—H30C	0.98
C15—H15B	0.98	N1—Cu1	1.9762 (19)
C15—H15C	0.98	N2—Cu1	1.9385 (19)
C16—N3	1.339 (3)	N3—Cu1	1.9650 (19)
C16—C17	1.426 (3)	N4—Cu1	1.9471 (19)
N1—C1—C2	110.9 (2)	C20—C19—N3	123.4 (2)
N1—C1—C10	122.6 (2)	C20—C19—C18	127.7 (2)
C2—C1—C10	126.5 (2)	N3—C19—C18	108.78 (18)
C3—C2—C1	106.8 (2)	C19—C20—C21	128.7 (2)
C3—C2—C11	127.4 (2)	C19—C20—H20	115.6
C1—C2—C11	125.8 (2)	C21—C20—H20	115.6
C2—C3—C4	106.9 (2)	N4—C21—C20	123.4 (2)
C2—C3—C12	126.1 (2)	N4—C21—C22	108.86 (19)
C4—C3—C12	127.0 (2)	C20—C21—C22	127.6 (2)
C5—C4—N1	123.5 (2)	C23—C22—C21	106.8 (2)
C5—C4—C3	127.6 (2)	C23—C22—C28	126.4 (2)
N1—C4—C3	108.9 (2)	C21—C22—C28	126.8 (2)
C6—C5—C4	129.1 (2)	C22—C23—C24	106.8 (2)
C6—C5—H5	115.5	C22—C23—C29	126.8 (2)
C4—C5—H5	115.5	C24—C23—C29	126.4 (2)
C5—C6—N2	122.2 (2)	N4—C24—C23	110.6 (2)
C5—C6—C7	129.2 (2)	N4—C24—C30	122.1 (2)
N2—C6—C7	108.6 (2)	C23—C24—C30	127.3 (2)
C8—C7—C6	106.7 (2)	C16—C25—H25A	109.5
C8—C7—C13	126.8 (2)	C16—C25—H25B	109.5
C6—C7—C13	126.5 (2)	H25A—C25—H25B	109.5
C7—C8—C9	106.7 (2)	C16—C25—H25C	109.5
C7—C8—C14	127.0 (2)	H25A—C25—H25C	109.5
C9—C8—C14	126.2 (2)	H25B—C25—H25C	109.5
N2—C9—C8	110.9 (2)	C17—C26—H26A	109.5
N2—C9—C15	121.2 (2)	C17—C26—H26B	109.5
C8—C9—C15	127.9 (2)	H26A—C26—H26B	109.5
C1—C10—H10A	109.5	C17—C26—H26C	109.5
C1—C10—H10B	109.5	H26A—C26—H26C	109.5
H10A—C10—H10B	109.5	H26B—C26—H26C	109.5
C1—C10—H10C	109.5	C18—C27—H27A	109.5
H10A—C10—H10C	109.5	C18—C27—H27B	109.5
H10B—C10—H10C	109.5	H27A—C27—H27B	109.5
C2—C11—H11A	109.5	C18—C27—H27C	109.5
C2—C11—H11B	109.5	H27A—C27—H27C	109.5
H11A—C11—H11B	109.5	H27B—C27—H27C	109.5
C2—C11—H11C	109.5	C22—C28—H28A	109.5
H11A—C11—H11C	109.5	C22—C28—H28B	109.5
H11B—C11—H11C	109.5	H28A—C28—H28B	109.5
C3—C12—H12A	109.5	C22—C28—H28C	109.5
C3—C12—H12B	109.5	H28A—C28—H28C	109.5
H12A—C12—H12B	109.5	H28B—C28—H28C	109.5
C3—C12—H12C	109.5	C23—C29—H29A	109.5
H12A—C12—H12C	109.5	C23—C29—H29B	109.5
H12B—C12—H12C	109.5	H29A—C29—H29B	109.5
C7—C13—H13A	109.5	C23—C29—H29C	109.5
C7—C13—H13B	109.5	H29A—C29—H29C	109.5
H13A—C13—H13B	109.5	H29B—C29—H29C	109.5
C7—C13—H13C	109.5	C24—C30—H30A	109.5
H13A—C13—H13C	109.5	C24—C30—H30B	109.5
H13B—C13—H13C	109.5	H30A—C30—H30B	109.5
C8—C14—H14A	109.5	C24—C30—H30C	109.5
C8—C14—H14B	109.5	H30A—C30—H30C	109.5
H14A—C14—H14B	109.5	H30B—C30—H30C	109.5
C8—C14—H14C	109.5	C1—N1—C4	106.43 (19)
H14A—C14—H14C	109.5	C1—N1—Cu1	128.71 (16)
H14B—C14—H14C	109.5	C4—N1—Cu1	121.56 (15)
C9—C15—H15A	109.5	C9—N2—C6	107.10 (19)
C9—C15—H15B	109.5	C9—N2—Cu1	127.50 (16)
H15A—C15—H15B	109.5	C6—N2—Cu1	125.33 (16)
C9—C15—H15C	109.5	C16—N3—C19	106.97 (18)
H15A—C15—H15C	109.5	C16—N3—Cu1	128.25 (15)
H15B—C15—H15C	109.5	C19—N3—Cu1	124.45 (14)
N3—C16—C17	111.2 (2)	C24—N4—C21	106.98 (18)
N3—C16—C25	123.5 (2)	C24—N4—Cu1	127.95 (16)
C17—C16—C25	125.3 (2)	C21—N4—Cu1	124.74 (15)
C18—C17—C16	106.57 (19)	N2—Cu1—N4	133.10 (8)
C18—C17—C26	128.8 (2)	N2—Cu1—N3	101.81 (8)
C16—C17—C26	124.7 (2)	N4—Cu1—N3	95.11 (8)
C17—C18—C19	106.50 (19)	N2—Cu1—N1	95.00 (8)
C17—C18—C27	127.7 (2)	N4—Cu1—N1	109.25 (8)
C19—C18—C27	125.8 (2)	N3—Cu1—N1	126.54 (8)
N1—C1—C2—C3	0.3 (3)	C2—C1—N1—C4	0.0 (2)
C10—C1—C2—C3	−179.1 (2)	C10—C1—N1—C4	179.4 (2)
N1—C1—C2—C11	179.5 (2)	C2—C1—N1—Cu1	−159.31 (16)
C10—C1—C2—C11	0.2 (4)	C10—C1—N1—Cu1	20.1 (3)
C1—C2—C3—C4	−0.4 (2)	C5—C4—N1—C1	179.0 (2)
C11—C2—C3—C4	−179.7 (2)	C3—C4—N1—C1	−0.3 (2)
C1—C2—C3—C12	177.4 (2)	C5—C4—N1—Cu1	−19.9 (3)
C11—C2—C3—C12	−1.8 (4)	C3—C4—N1—Cu1	160.86 (15)
C2—C3—C4—C5	−178.8 (2)	C8—C9—N2—C6	0.2 (2)
C12—C3—C4—C5	3.4 (4)	C15—C9—N2—C6	178.6 (2)
C2—C3—C4—N1	0.4 (3)	C8—C9—N2—Cu1	177.39 (15)
C12—C3—C4—N1	−177.4 (2)	C15—C9—N2—Cu1	−4.3 (3)
N1—C4—C5—C6	5.1 (4)	C5—C6—N2—C9	177.6 (2)
C3—C4—C5—C6	−175.8 (2)	C7—C6—N2—C9	−0.5 (2)
C4—C5—C6—N2	5.8 (4)	C5—C6—N2—Cu1	0.3 (3)
C4—C5—C6—C7	−176.6 (2)	C7—C6—N2—Cu1	−177.68 (14)
C5—C6—C7—C8	−177.3 (2)	C17—C16—N3—C19	−0.8 (3)
N2—C6—C7—C8	0.5 (2)	C25—C16—N3—C19	178.2 (2)
C5—C6—C7—C13	4.7 (4)	C17—C16—N3—Cu1	−174.31 (15)
N2—C6—C7—C13	−177.5 (2)	C25—C16—N3—Cu1	4.6 (3)
C6—C7—C8—C9	−0.3 (2)	C20—C19—N3—C16	−176.4 (2)
C13—C7—C8—C9	177.6 (2)	C18—C19—N3—C16	1.2 (2)
C6—C7—C8—C14	−178.6 (2)	C20—C19—N3—Cu1	−2.5 (3)
C13—C7—C8—C14	−0.6 (4)	C18—C19—N3—Cu1	175.09 (15)
C7—C8—C9—N2	0.1 (3)	C23—C24—N4—C21	0.5 (3)
C14—C8—C9—N2	178.3 (2)	C30—C24—N4—C21	179.0 (2)
C7—C8—C9—C15	−178.1 (2)	C23—C24—N4—Cu1	−173.08 (16)
C14—C8—C9—C15	0.2 (4)	C30—C24—N4—Cu1	5.5 (3)
N3—C16—C17—C18	0.0 (3)	C20—C21—N4—C24	−176.6 (2)
C25—C16—C17—C18	−178.9 (2)	C22—C21—N4—C24	0.1 (3)
N3—C16—C17—C26	179.8 (2)	C20—C21—N4—Cu1	−2.8 (3)
C25—C16—C17—C26	0.8 (4)	C22—C21—N4—Cu1	173.90 (15)
C16—C17—C18—C19	0.8 (2)	C9—N2—Cu1—N4	50.3 (2)
C26—C17—C18—C19	−179.0 (2)	C6—N2—Cu1—N4	−133.06 (17)
C16—C17—C18—C27	179.9 (2)	C9—N2—Cu1—N3	−58.40 (19)
C26—C17—C18—C27	0.2 (4)	C6—N2—Cu1—N3	118.25 (18)
C17—C18—C19—C20	176.2 (2)	C9—N2—Cu1—N1	172.63 (18)
C27—C18—C19—C20	−3.0 (4)	C6—N2—Cu1—N1	−10.71 (18)
C17—C18—C19—N3	−1.2 (3)	C24—N4—Cu1—N2	62.3 (2)
C27—C18—C19—N3	179.6 (2)	C21—N4—Cu1—N2	−110.21 (19)
N3—C19—C20—C21	1.0 (4)	C24—N4—Cu1—N3	173.7 (2)
C18—C19—C20—C21	−176.1 (2)	C21—N4—Cu1—N3	1.21 (19)
C19—C20—C21—N4	1.9 (4)	C24—N4—Cu1—N1	−54.6 (2)
C19—C20—C21—C22	−174.2 (2)	C21—N4—Cu1—N1	132.85 (18)
N4—C21—C22—C23	−0.6 (3)	C16—N3—Cu1—N2	−50.2 (2)
C20—C21—C22—C23	175.9 (2)	C19—N3—Cu1—N2	137.32 (18)
N4—C21—C22—C28	−179.6 (2)	C16—N3—Cu1—N4	173.8 (2)
C20—C21—C22—C28	−3.0 (4)	C19—N3—Cu1—N4	1.31 (19)
C21—C22—C23—C24	0.9 (3)	C16—N3—Cu1—N1	55.3 (2)
C28—C22—C23—C24	179.8 (2)	C19—N3—Cu1—N1	−117.27 (18)
C21—C22—C23—C29	−178.0 (2)	C1—N1—Cu1—N2	176.26 (19)
C28—C22—C23—C29	0.9 (4)	C4—N1—Cu1—N2	19.68 (18)
C22—C23—C24—N4	−0.9 (3)	C1—N1—Cu1—N4	−44.5 (2)
C29—C23—C24—N4	178.1 (2)	C4—N1—Cu1—N4	158.88 (16)
C22—C23—C24—C30	−179.3 (2)	C1—N1—Cu1—N3	67.6 (2)
C29—C23—C24—C30	−0.4 (4)	C4—N1—Cu1—N3	−89.01 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C29—H29C···Cgi	0.98	2.78	3.551 (3)	136

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the N3/C16–C19 pyrrole ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C29—H29C⋯Cg i	0.98	2.78	3.551 (3)	136

Symmetry code: (i) .