Crystal structure of bis-(4-nitro-aniline-κN (1))(5,10,15,20-tetra-phenyl-por-phy-rin-ato-κ(4) N)cobalt(III) chloride di-chloro-methane monosolvate.

The reaction of [Co(III)(TPP)Cl] (TPP is the dianion of 5,10,15,20-tetra-phenyl-porphyrin) with an excess of 4-nitro-aniline in di-chloro-methane leads to the title compound, [Co(III)(C44H28N4)(C6H6N2O2)2]Cl·CH2Cl2. The Co(III) ion lies on an inversion centre and is octa-hedrally coordinated by two N atoms of the NH2 groups of the two 4-nitro-aniline trans-axial ligands and four pyrrole N atoms of the porphyrin. The asymmetric unit contains one half of the [Co(III)(TPP)(4-nitro-aniline)2](+) ion complex, one chloride counter-ion (lying on a twofold rotation axis) and one half di-chloro-methane solvent mol-ecule, where the C atom lies on a twofold rotation axis. The average equatorial Co-N(pyrrole) distance (Co-Np) is 1.982 (2) Å and the axial Co-N(4-nitro-aniline) bond length is 2.006 (2) Å. The crystal packing is stabilized by an N-H⋯Cl hydrogen bond between the N atom of the amino group of the 4-nitro-aniline axial ligand and the chloride counter-ion. The supra-molecular architecture is further stabilized by weak C-H⋯π inter-actions.

Related literature

For the synthesis of the title compound, see: Madure & Scheidt (1976 ▶). For related structures, see: n class="Chemical">Dhifet et al. (2010 ▶); Konarev et al. (2003 ▶); Jentzen et al. (1995 ▶); Mansour et al. (2013 ▶); Zhang et al. (2005 ▶); Feng (2012 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

[Co(C44H28n class="Chemical">N4)(C6H6N2O2)2]Cl·CH2Cl2

M = 1068.30

Monoclinic,

a = 13.3527 (9) Å

b = 12.4492 (10) Å

c = 14.8935 (14) Å

β = 95.604 (4)°

V = 2463.9 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.57 mm−1

T = 150 K

0.40 × 0.24 × 0.11 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2006 ▶) T min = 0.819, T max = 0.939

20514 measured reflections

4853 independent reflections

4083 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.097

S = 1.04

4853 reflections

338 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.63 e Å−3

Δρmin = −0.96 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶) and ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) I, n class="Chemical">New_Global_Publ_Block. DOI: 10.1107/S1600536814016274/xu5802sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814016274/xu5802Isup2.hkl

Click here for additional data file.

ORTEP . DOI: 10.1107/S1600536814016274/xu5802fig1.tif

An ORTEP view of the mol­ecular structure of the title mol­ecule with the atom-numbering. Displacement ellipsoids are drawn at 50%. The H atoms have been omitted for clarity.

Click here for additional data file.

. DOI: 10.1107/S1600536814016274/xu5802fig2.tif

The crystal structure of the title compound plotted in projection along [100]. H atoms have been omitted.

CCDC reference: 1013796

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

[Co(C44H28N4)(C6H6N2O2)2]Cl·CH2Cl2	F(000) = 1100
Mr = 1068.30	Dx = 1.440 Mg m−3
Monoclinic, P2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yC	Cell parameters from 22812 reflections
a = 13.3527 (9) Å	θ = 3.0–26.0°
b = 12.4492 (10) Å	µ = 0.57 mm−1
c = 14.8935 (14) Å	T = 150 K
β = 95.604 (4)°	Prism, black
V = 2463.9 (3) Å3	0.40 × 0.24 × 0.11 mm
Z = 2

Bruker APEXII diffractometer	4853 independent reflections
Radiation source: fine-focus sealed tube	4083 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
CCD rotation images, thin slices scans	θmax = 26.0°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −15→16
Tmin = 0.819, Tmax = 0.939	k = −15→13
20514 measured reflections	l = −18→18

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.037P)2 + 2.4863P] where P = (Fo2 + 2Fc2)/3
4853 reflections	(Δ/σ)max = 0.001
338 parameters	Δρmax = 0.63 e Å−3
0 restraints	Δρmin = −0.96 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2sigma(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	Occ. (<1)
Co1	0.0000	0.0000	0.5000	0.01228 (11)
N1	0.02932 (12)	−0.15405 (13)	0.48224 (11)	0.0141 (4)
N2	−0.14475 (12)	−0.03522 (14)	0.50284 (11)	0.0151 (4)
N3	0.01549 (13)	−0.01847 (15)	0.63444 (12)	0.0163 (4)
H3A	−0.034 (2)	−0.061 (3)	0.640 (2)	0.050*
H3B	0.007 (2)	0.046 (3)	0.656 (2)	0.050*
N4	0.37671 (17)	−0.1997 (2)	0.79687 (15)	0.0439 (6)
O1	0.44300 (15)	−0.1385 (2)	0.82761 (14)	0.0564 (6)
O2	0.38324 (17)	−0.2986 (2)	0.79970 (15)	0.0616 (7)
C1	−0.03818 (15)	−0.23849 (16)	0.47479 (13)	0.0161 (4)
C2	−0.14203 (15)	−0.23050 (17)	0.47355 (14)	0.0170 (4)
C3	−0.19067 (15)	−0.13424 (17)	0.48748 (14)	0.0164 (4)
C4	−0.29731 (16)	−0.12384 (18)	0.48996 (15)	0.0218 (5)
H4	−0.3456	−0.1796	0.4797	0.026*
C5	−0.31655 (16)	−0.02085 (18)	0.50949 (15)	0.0215 (5)
H5	−0.3805	0.0090	0.5176	0.026*
C6	−0.22209 (15)	0.03581 (17)	0.51590 (14)	0.0160 (4)
C7	−0.21196 (15)	0.14533 (17)	0.53055 (14)	0.0168 (4)
C8	−0.12188 (15)	0.19990 (17)	0.52819 (14)	0.0163 (4)
C9	−0.11209 (16)	0.31445 (17)	0.53702 (15)	0.0206 (5)
H9	−0.1649	0.3642	0.5434	0.025*
C10	−0.01374 (16)	0.33815 (17)	0.53458 (15)	0.0200 (5)
H10	0.0156	0.4077	0.5384	0.024*
C11	−0.20377 (15)	−0.32921 (17)	0.45060 (15)	0.0188 (4)
C12	−0.25842 (16)	−0.38074 (18)	0.51311 (16)	0.0236 (5)
H12	−0.2578	−0.3531	0.5726	0.028*
C13	−0.31392 (17)	−0.47253 (19)	0.48862 (19)	0.0305 (6)
H13	−0.3504	−0.5076	0.5318	0.037*
C14	−0.31641 (18)	−0.51302 (19)	0.40228 (19)	0.0321 (6)
H14	−0.3542	−0.5759	0.3861	0.038*
C15	−0.26382 (18)	−0.46183 (19)	0.33937 (18)	0.0313 (6)
H15	−0.2661	−0.4890	0.2796	0.038*
C16	−0.20733 (17)	−0.37009 (18)	0.36355 (16)	0.0253 (5)
H16	−0.1710	−0.3353	0.3201	0.030*
C17	−0.30262 (15)	0.20696 (16)	0.55320 (14)	0.0172 (4)
C18	−0.38252 (15)	0.22896 (18)	0.48905 (15)	0.0203 (5)
H18	−0.3799	0.2061	0.4285	0.024*
C19	−0.46643 (16)	0.28433 (18)	0.51305 (16)	0.0232 (5)
H19	−0.5203	0.3001	0.4685	0.028*
C20	−0.47187 (16)	0.31632 (19)	0.60080 (17)	0.0267 (5)
H20	−0.5298	0.3531	0.6171	0.032*
C21	−0.39250 (18)	0.2947 (2)	0.66542 (17)	0.0313 (6)
H21	−0.3961	0.3163	0.7262	0.038*
C22	−0.30775 (17)	0.24141 (19)	0.64141 (16)	0.0262 (5)
H22	−0.2528	0.2284	0.6856	0.031*
C23	0.10649 (15)	−0.06513 (17)	0.67693 (13)	0.0179 (4)
C24	0.11492 (17)	−0.17626 (19)	0.68680 (15)	0.0232 (5)
H24	0.0600	−0.2215	0.6668	0.028*
C25	0.20399 (19)	−0.2201 (2)	0.72605 (16)	0.0311 (6)
H25	0.2110	−0.2957	0.7331	0.037*
C26	0.28217 (18)	−0.1523 (2)	0.75473 (15)	0.0307 (6)
C27	0.27532 (17)	−0.0420 (2)	0.74682 (16)	0.0304 (6)
H27	0.3302	0.0028	0.7679	0.036*
C28	0.18596 (17)	0.00184 (19)	0.70711 (15)	0.0237 (5)
H28	0.1793	0.0775	0.7006	0.028*
Cl2	0.0000	0.19408 (6)	0.7500	0.02607 (19)
Cl1	−0.07442 (8)	0.55949 (7)	0.67168 (6)	0.0712 (3)
C29	0.0000	0.4862 (4)	0.7500	0.0670 (15)
H29A	−0.0441	0.4391	0.7825	0.080*	0.50
H29B	0.0441	0.4391	0.7175	0.080*	0.50

	U11	U22	U33	U12	U13	U23
Co1	0.01021 (19)	0.0130 (2)	0.0136 (2)	0.00020 (14)	0.00090 (14)	−0.00036 (15)
N1	0.0125 (8)	0.0149 (9)	0.0149 (9)	−0.0002 (7)	0.0015 (6)	0.0006 (7)
N2	0.0136 (8)	0.0149 (9)	0.0170 (9)	0.0001 (7)	0.0018 (7)	−0.0012 (7)
N3	0.0151 (9)	0.0171 (10)	0.0164 (9)	−0.0001 (7)	0.0007 (7)	0.0000 (7)
N4	0.0283 (13)	0.078 (2)	0.0256 (12)	0.0227 (13)	0.0045 (10)	0.0145 (12)
O1	0.0248 (10)	0.106 (2)	0.0370 (12)	0.0146 (12)	−0.0023 (9)	0.0107 (12)
O2	0.0546 (14)	0.0739 (18)	0.0554 (14)	0.0394 (12)	0.0005 (11)	0.0199 (12)
C1	0.0178 (10)	0.0154 (10)	0.0151 (10)	−0.0008 (8)	0.0015 (8)	0.0008 (8)
C2	0.0158 (10)	0.0172 (11)	0.0177 (11)	−0.0016 (8)	0.0011 (8)	0.0009 (8)
C3	0.0161 (10)	0.0174 (11)	0.0157 (10)	−0.0028 (8)	0.0018 (8)	0.0005 (8)
C4	0.0148 (10)	0.0199 (12)	0.0306 (13)	−0.0030 (9)	0.0020 (9)	−0.0009 (9)
C5	0.0123 (10)	0.0228 (12)	0.0298 (12)	−0.0004 (8)	0.0043 (9)	−0.0022 (9)
C6	0.0127 (10)	0.0194 (11)	0.0160 (10)	0.0007 (8)	0.0021 (8)	−0.0006 (8)
C7	0.0144 (10)	0.0195 (11)	0.0163 (10)	0.0031 (8)	−0.0002 (8)	−0.0012 (8)
C8	0.0159 (10)	0.0173 (11)	0.0154 (10)	0.0020 (8)	0.0005 (8)	−0.0005 (8)
C9	0.0177 (10)	0.0179 (11)	0.0257 (12)	0.0038 (9)	0.0000 (9)	−0.0002 (9)
C10	0.0212 (11)	0.0136 (11)	0.0250 (12)	−0.0002 (8)	0.0002 (9)	0.0009 (9)
C11	0.0122 (10)	0.0149 (11)	0.0289 (12)	0.0021 (8)	0.0003 (8)	0.0015 (9)
C12	0.0198 (11)	0.0193 (12)	0.0317 (13)	0.0011 (9)	0.0025 (9)	0.0035 (9)
C13	0.0183 (11)	0.0211 (12)	0.0517 (17)	−0.0021 (9)	0.0024 (11)	0.0121 (11)
C14	0.0210 (12)	0.0164 (12)	0.0570 (18)	−0.0022 (9)	−0.0058 (11)	0.0011 (11)
C15	0.0285 (13)	0.0226 (13)	0.0416 (15)	0.0005 (10)	−0.0034 (11)	−0.0092 (11)
C16	0.0227 (11)	0.0231 (12)	0.0300 (13)	−0.0020 (9)	0.0017 (9)	−0.0003 (10)
C17	0.0134 (10)	0.0139 (10)	0.0245 (11)	−0.0003 (8)	0.0031 (8)	−0.0007 (8)
C18	0.0157 (10)	0.0212 (11)	0.0241 (12)	−0.0018 (9)	0.0018 (8)	−0.0025 (9)
C19	0.0140 (10)	0.0232 (12)	0.0319 (13)	−0.0010 (9)	0.0000 (9)	0.0026 (10)
C20	0.0172 (11)	0.0263 (13)	0.0377 (14)	0.0061 (9)	0.0089 (10)	−0.0027 (10)
C21	0.0320 (13)	0.0371 (15)	0.0256 (13)	0.0085 (11)	0.0073 (10)	−0.0076 (11)
C22	0.0220 (11)	0.0306 (13)	0.0253 (12)	0.0069 (10)	−0.0012 (9)	−0.0026 (10)
C23	0.0188 (10)	0.0233 (12)	0.0116 (10)	0.0043 (9)	0.0020 (8)	0.0021 (8)
C24	0.0265 (12)	0.0240 (12)	0.0190 (11)	0.0021 (9)	0.0020 (9)	0.0023 (9)
C25	0.0378 (14)	0.0310 (14)	0.0251 (13)	0.0130 (11)	0.0061 (10)	0.0081 (10)
C26	0.0245 (12)	0.0509 (17)	0.0165 (12)	0.0146 (11)	0.0011 (9)	0.0084 (11)
C27	0.0204 (12)	0.0479 (16)	0.0222 (12)	−0.0027 (11)	−0.0011 (9)	0.0022 (11)
C28	0.0233 (11)	0.0276 (12)	0.0197 (11)	−0.0018 (9)	−0.0009 (9)	0.0004 (9)
Cl2	0.0409 (5)	0.0192 (4)	0.0185 (4)	0.000	0.0051 (3)	0.000
Cl1	0.1153 (8)	0.0558 (5)	0.0398 (5)	0.0400 (5)	−0.0065 (5)	−0.0044 (4)
C29	0.059 (3)	0.045 (3)	0.089 (4)	0.000	−0.033 (3)	0.000

Co1—N1i	1.9802 (17)	C11—C12	1.394 (3)
Co1—N1	1.9802 (17)	C12—C13	1.391 (3)
Co1—N2i	1.9863 (16)	C12—H12	0.9500
Co1—N2	1.9863 (16)	C13—C14	1.379 (4)
Co1—N3i	2.0060 (17)	C13—H13	0.9500
Co1—N3	2.0060 (17)	C14—C15	1.380 (4)
N1—C1	1.382 (3)	C14—H14	0.9500
N1—C8i	1.384 (3)	C15—C16	1.396 (3)
N2—C3	1.386 (3)	C15—H15	0.9500
N2—C6	1.388 (3)	C16—H16	0.9500
N3—C23	1.437 (3)	C17—C22	1.390 (3)
N3—H3A	0.86 (3)	C17—C18	1.388 (3)
N3—H3B	0.87 (3)	C18—C19	1.392 (3)
N4—O1	1.223 (3)	C18—H18	0.9500
N4—O2	1.234 (4)	C19—C20	1.375 (3)
N4—C26	1.477 (3)	C19—H19	0.9500
C1—C2	1.389 (3)	C20—C21	1.387 (3)
C1—C10i	1.435 (3)	C20—H20	0.9500
C2—C3	1.388 (3)	C21—C22	1.388 (3)
C2—C11	1.500 (3)	C21—H21	0.9500
C3—C4	1.434 (3)	C22—H22	0.9500
C4—C5	1.345 (3)	C23—C28	1.389 (3)
C4—H4	0.9500	C23—C24	1.395 (3)
C5—C6	1.440 (3)	C24—C25	1.385 (3)
C5—H5	0.9500	C24—H24	0.9500
C6—C7	1.385 (3)	C25—C26	1.378 (4)
C7—C8	1.385 (3)	C25—H25	0.9500
C7—C17	1.499 (3)	C26—C27	1.380 (4)
C8—N1i	1.384 (3)	C27—C28	1.391 (3)
C8—C9	1.437 (3)	C27—H27	0.9500
C9—C10	1.350 (3)	C28—H28	0.9500
C9—H9	0.9500	Cl1—C29	1.719 (3)
C10—C1i	1.435 (3)	C29—Cl1ii	1.719 (3)
C10—H10	0.9500	C29—H29A	0.9900
C11—C16	1.389 (3)	C29—H29B	0.9900
N1i—Co1—N1	180.0	C16—C11—C12	118.8 (2)
N1i—Co1—N2i	89.69 (7)	C16—C11—C2	118.72 (19)
N1—Co1—N2i	90.31 (7)	C12—C11—C2	122.5 (2)
N1i—Co1—N2	90.31 (7)	C13—C12—C11	120.2 (2)
N1—Co1—N2	89.69 (7)	C13—C12—H12	119.9
N2i—Co1—N2	180.0	C11—C12—H12	119.9
N1i—Co1—N3i	91.14 (7)	C14—C13—C12	120.6 (2)
N1—Co1—N3i	88.86 (7)	C14—C13—H13	119.7
N2i—Co1—N3i	87.66 (7)	C12—C13—H13	119.7
N2—Co1—N3i	92.34 (7)	C13—C14—C15	119.8 (2)
N1i—Co1—N3	88.86 (7)	C13—C14—H14	120.1
N1—Co1—N3	91.14 (7)	C15—C14—H14	120.1
N2i—Co1—N3	92.34 (7)	C14—C15—C16	120.0 (2)
N2—Co1—N3	87.66 (7)	C14—C15—H15	120.0
N3i—Co1—N3	180.000 (15)	C16—C15—H15	120.0
C1—N1—C8i	105.06 (16)	C11—C16—C15	120.6 (2)
C1—N1—Co1	127.70 (13)	C11—C16—H16	119.7
C8i—N1—Co1	127.22 (14)	C15—C16—H16	119.7
C3—N2—C6	105.46 (16)	C22—C17—C18	118.96 (19)
C3—N2—Co1	127.49 (13)	C22—C17—C7	119.08 (19)
C6—N2—Co1	126.97 (14)	C18—C17—C7	121.95 (19)
C23—N3—Co1	119.10 (13)	C17—C18—C19	120.3 (2)
C23—N3—H3A	110 (2)	C17—C18—H18	119.8
Co1—N3—H3A	100 (2)	C19—C18—H18	119.8
C23—N3—H3B	111 (2)	C20—C19—C18	120.4 (2)
Co1—N3—H3B	105 (2)	C20—C19—H19	119.8
H3A—N3—H3B	113 (3)	C18—C19—H19	119.8
O1—N4—O2	124.2 (2)	C19—C20—C21	119.7 (2)
O1—N4—C26	117.9 (3)	C19—C20—H20	120.1
O2—N4—C26	117.9 (3)	C21—C20—H20	120.1
N1—C1—C2	126.09 (19)	C22—C21—C20	120.1 (2)
N1—C1—C10i	110.37 (17)	C22—C21—H21	120.0
C2—C1—C10i	123.51 (19)	C20—C21—H21	120.0
C3—C2—C1	122.76 (19)	C17—C22—C21	120.5 (2)
C3—C2—C11	119.10 (17)	C17—C22—H22	119.8
C1—C2—C11	118.04 (18)	C21—C22—H22	119.8
C2—C3—N2	125.91 (18)	C28—C23—C24	120.7 (2)
C2—C3—C4	124.20 (19)	C28—C23—N3	119.1 (2)
N2—C3—C4	109.87 (18)	C24—C23—N3	120.2 (2)
C5—C4—C3	107.63 (19)	C25—C24—C23	119.5 (2)
C5—C4—H4	126.2	C25—C24—H24	120.2
C3—C4—H4	126.2	C23—C24—H24	120.2
C4—C5—C6	107.25 (18)	C26—C25—C24	118.8 (2)
C4—C5—H5	126.4	C26—C25—H25	120.6
C6—C5—H5	126.4	C24—C25—H25	120.6
C7—C6—N2	125.92 (18)	C25—C26—C27	122.8 (2)
C7—C6—C5	124.32 (19)	C25—C26—N4	118.5 (2)
N2—C6—C5	109.74 (18)	C27—C26—N4	118.7 (2)
C6—C7—C8	123.40 (19)	C26—C27—C28	118.3 (2)
C6—C7—C17	118.07 (18)	C26—C27—H27	120.9
C8—C7—C17	118.49 (19)	C28—C27—H27	120.9
C7—C8—N1i	126.01 (19)	C23—C28—C27	119.9 (2)
C7—C8—C9	123.79 (19)	C23—C28—H28	120.0
N1i—C8—C9	110.20 (18)	C27—C28—H28	120.0
C10—C9—C8	107.13 (19)	Cl1ii—C29—Cl1	115.8 (3)
C10—C9—H9	126.4	Cl1ii—C29—H29A	108.3
C8—C9—H9	126.4	Cl1—C29—H29A	108.3
C9—C10—C1i	107.11 (19)	Cl1ii—C29—H29B	108.3
C9—C10—H10	126.4	Cl1—C29—H29B	108.3
C1i—C10—H10	126.4	H29A—C29—H29B	107.4
N1i—Co1—N1—C1	32 (100)	C5—C6—C7—C8	−173.8 (2)
N2i—Co1—N1—C1	−178.83 (17)	N2—C6—C7—C17	−173.47 (19)
N2—Co1—N1—C1	1.17 (17)	C5—C6—C7—C17	8.3 (3)
N3i—Co1—N1—C1	−91.18 (17)	C6—C7—C8—N1i	−4.9 (3)
N3—Co1—N1—C1	88.82 (17)	C17—C7—C8—N1i	172.92 (19)
N1i—Co1—N1—C8i	−150 (100)	C6—C7—C8—C9	175.5 (2)
N2i—Co1—N1—C8i	−1.01 (17)	C17—C7—C8—C9	−6.7 (3)
N2—Co1—N1—C8i	178.99 (17)	C7—C8—C9—C10	178.0 (2)
N3i—Co1—N1—C8i	86.64 (17)	N1i—C8—C9—C10	−1.7 (2)
N3—Co1—N1—C8i	−93.36 (17)	C8—C9—C10—C1i	−0.6 (2)
N1i—Co1—N2—C3	174.74 (17)	C3—C2—C11—C16	108.9 (2)
N1—Co1—N2—C3	−5.26 (17)	C1—C2—C11—C16	−67.5 (3)
N2i—Co1—N2—C3	−10 (11)	C3—C2—C11—C12	−70.5 (3)
N3i—Co1—N2—C3	83.59 (17)	C1—C2—C11—C12	113.2 (2)
N3—Co1—N2—C3	−96.41 (17)	C16—C11—C12—C13	1.1 (3)
N1i—Co1—N2—C6	−1.48 (17)	C2—C11—C12—C13	−179.5 (2)
N1—Co1—N2—C6	178.52 (17)	C11—C12—C13—C14	−0.6 (3)
N2i—Co1—N2—C6	173 (11)	C12—C13—C14—C15	−0.3 (4)
N3i—Co1—N2—C6	−92.63 (17)	C13—C14—C15—C16	0.8 (4)
N3—Co1—N2—C6	87.37 (17)	C12—C11—C16—C15	−0.7 (3)
N1i—Co1—N3—C23	−125.89 (16)	C2—C11—C16—C15	180.0 (2)
N1—Co1—N3—C23	54.11 (16)	C14—C15—C16—C11	−0.3 (4)
N2i—Co1—N3—C23	−36.25 (16)	C6—C7—C17—C22	105.9 (2)
N2—Co1—N3—C23	143.75 (16)	C8—C7—C17—C22	−72.1 (3)
N3i—Co1—N3—C23	88 (33)	C6—C7—C17—C18	−72.9 (3)
C8i—N1—C1—C2	−174.5 (2)	C8—C7—C17—C18	109.1 (2)
Co1—N1—C1—C2	3.7 (3)	C22—C17—C18—C19	−0.2 (3)
C8i—N1—C1—C10i	3.7 (2)	C7—C17—C18—C19	178.6 (2)
Co1—N1—C1—C10i	−178.12 (14)	C17—C18—C19—C20	−1.1 (3)
N1—C1—C2—C3	−5.6 (3)	C18—C19—C20—C21	1.0 (4)
C10i—C1—C2—C3	176.5 (2)	C19—C20—C21—C22	0.3 (4)
N1—C1—C2—C11	170.66 (19)	C18—C17—C22—C21	1.6 (3)
C10i—C1—C2—C11	−7.3 (3)	C7—C17—C22—C21	−177.3 (2)
C1—C2—C3—N2	0.9 (3)	C20—C21—C22—C17	−1.6 (4)
C11—C2—C3—N2	−175.24 (19)	Co1—N3—C23—C28	91.4 (2)
C1—C2—C3—C4	−177.6 (2)	Co1—N3—C23—C24	−88.0 (2)
C11—C2—C3—C4	6.2 (3)	C28—C23—C24—C25	−0.8 (3)
C6—N2—C3—C2	−178.0 (2)	N3—C23—C24—C25	178.53 (19)
Co1—N2—C3—C2	5.2 (3)	C23—C24—C25—C26	0.2 (3)
C6—N2—C3—C4	0.7 (2)	C24—C25—C26—C27	0.6 (4)
Co1—N2—C3—C4	−176.13 (14)	C24—C25—C26—N4	179.7 (2)
C2—C3—C4—C5	176.8 (2)	O1—N4—C26—C25	−175.1 (2)
N2—C3—C4—C5	−2.0 (3)	O2—N4—C26—C25	4.1 (3)
C3—C4—C5—C6	2.3 (3)	O1—N4—C26—C27	4.0 (3)
C3—N2—C6—C7	−177.7 (2)	O2—N4—C26—C27	−176.8 (2)
Co1—N2—C6—C7	−0.8 (3)	C25—C26—C27—C28	−0.9 (4)
C3—N2—C6—C5	0.7 (2)	N4—C26—C27—C28	−179.9 (2)
Co1—N2—C6—C5	177.58 (14)	C24—C23—C28—C27	0.6 (3)
C4—C5—C6—C7	176.5 (2)	N3—C23—C28—C27	−178.75 (19)
C4—C5—C6—N2	−1.9 (3)	C26—C27—C28—C23	0.2 (3)
N2—C6—C7—C8	4.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3B···Cl2	0.88 (4)	2.32 (3)	3.174 (2)	164 (3)
C13—H13···Cg8iii	0.95	3.00	3.723 (3)	134
C20—H20···Cg7iv	0.95	2.94	3.788 (2)	150

Table 1

Hydrogen-bond geometry (Å, °)

Cg7 and Cg8 are the centroids of the C11/C12–C16 and C17/C18–C22 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3B⋯Cl2	0.88 (4)	2.32 (3)	3.174 (2)	164 (3)
C13—H13⋯Cg8i	0.95	3.00	3.723 (3)	134
C20—H20⋯Cg7ii	0.95	2.94	3.788 (2)	150

Symmetry codes: (i) ; (ii) .