{2,2'-[1,1'-(Ethane-1,2-diyldinitrilo)-diethyl-idyne]diphenolato}bis-(pyrrolidine)cobalt(III) perchlorate p-xylene hemisolvate.

In the mononuclear title complex, [Co(C(18)H(18)N(2)O(2))(C(4)H(9)N)(2)]ClO(4)·0.5C(8)H(10), the Co(III) ion has a slightly distorted octa-hedral coordination geometry. In the Me-salen ligand, the benzene rings are almost parallel, making a dihedral angle of 0.48 (13)°, but the torsion angle along the central C-C bond is 41.1 (2)°·The pyrrolidine rings are in slightly distorted chair conformations. The N atoms of the pyrrolidine axial ligands are involved in N-H⋯O hydrogen bonds with the perchlorate anions, and these hydrogen bonds connect the ionic species into infinite chains along the b axis. Some relatively short C-H⋯π inter-actions are also present in the crystal structure and C-H⋯O inter-actions occur. The guest solvent p-xylene mol-ecule lies on a special position at the inversion centre.

Related literature

For the properties of Co(III) n class="Chemical">complexes with Schiff base ligands, see: Polson et al. (1997 ▶); Yamada et al. (1999 ▶); Henson et al. (1999 ▶); Bianchini & Zoeliner (1997 ▶); Mishra et al. (2008 ▶); Kumar et al. (2009 ▶). For related structures, see: Dreos et al. (2003 ▶). For the preparation of N,N′-bis­(methyl­salicyl­idene)-1,2-ethyl­enediamine, see: Hariharan & Urbach (1969 ▶).

Experimental

Crystal data

[Co(C18H18N2O2)(C4H9N)2]ClO4·0.n class="Chemical">5C8H10

M = 648.05

Monoclinic,

a = 13.118 (2) Å

b = 16.551 (3) Å

c = 13.784 (2) Å

β = 92.87 (2)°

V = 2989.0 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.71 mm−1

T = 100 K

0.40 × 0.15 × 0.15 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.422, T max = 1.000

23760 measured reflections

7081 independent reflections

4734 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.084

S = 0.99

7081 reflections

502 parameters

H atoms treated by a mixture of independent and n class="Chemical">constrained refinement

Δρmax = 0.67 e Å−3

Δρmin = −0.51 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Stereochemical Workstation Operation Manual (Siemens, 1989 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681004660X/jh2227sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681004660X/jh2227Isup2.hkl

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

[Co(C18H18N2O2)(C4H9N)2]ClO4·0.5C8H10	F(000) = 1364
Mr = 648.05	Dx = 1.440 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9456 reflections
a = 13.118 (2) Å	θ = 2.9–29.0°
b = 16.551 (3) Å	µ = 0.71 mm−1
c = 13.784 (2) Å	T = 100 K
β = 92.87 (2)°	Prism, dark red
V = 2989.0 (8) Å3	0.4 × 0.15 × 0.15 mm
Z = 4

Oxford Diffraction Xcalibur Eos diffractometer	7081 independent reflections
Radiation source: Enhance (Mo) X-ray Source	4734 reflections with I > 2σ(I)
graphite	Rint = 0.053
Detector resolution: 16.1544 pixels mm-1	θmax = 29.1°, θmin = 2.9°
ω scans	h = −16→15
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −21→22
Tmin = 0.422, Tmax = 1.000	l = −18→18
23760 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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.084	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ2(Fo2) + (0.038P)2] where P = (Fo2 + 2Fc2)/3
7081 reflections	(Δ/σ)max = 0.002
502 parameters	Δρmax = 0.67 e Å−3
0 restraints	Δρmin = −0.51 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 > 2σ(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
Co1	0.43307 (2)	0.200878 (17)	0.223086 (19)	0.01430 (8)
N1	0.32241 (13)	0.26626 (11)	0.15288 (13)	0.0195 (4)
H1	0.3269 (16)	0.2648 (13)	0.0877 (17)	0.023*
C2	0.31534 (19)	0.35365 (14)	0.17595 (19)	0.0280 (6)
H21	0.3731 (18)	0.3871 (15)	0.1487 (16)	0.034*
H22	0.3120 (17)	0.3579 (14)	0.2515 (17)	0.034*
C3	0.21166 (19)	0.37890 (16)	0.1324 (2)	0.0317 (6)
H31	0.1857 (17)	0.4294 (16)	0.1617 (17)	0.038*
H32	0.2132 (18)	0.3776 (15)	0.0624 (18)	0.038*
C4	0.1450 (2)	0.30912 (17)	0.1558 (3)	0.0427 (7)
H41	0.085 (2)	0.3023 (16)	0.107 (2)	0.051*
H42	0.121 (2)	0.3201 (17)	0.218 (2)	0.051*
C5	0.21586 (18)	0.23502 (15)	0.16164 (19)	0.0262 (5)
H51	0.2149 (17)	0.2099 (14)	0.2271 (17)	0.031*
H52	0.1983 (18)	0.1966 (15)	0.1083 (17)	0.031*
N6	0.53743 (14)	0.13130 (11)	0.29580 (11)	0.0160 (4)
H6	0.5884 (16)	0.1644 (14)	0.3137 (15)	0.019*
C7	0.50197 (19)	0.09102 (14)	0.38566 (15)	0.0207 (5)
H71	0.4302 (17)	0.0819 (14)	0.3787 (15)	0.025*
H72	0.5138 (16)	0.1294 (14)	0.4397 (15)	0.025*
C8	0.5615 (2)	0.01142 (15)	0.39679 (17)	0.0260 (5)
H81	0.5990 (17)	0.0093 (14)	0.4590 (17)	0.031*
H82	0.5160 (17)	−0.0334 (15)	0.3918 (16)	0.031*
C9	0.63361 (18)	0.00956 (15)	0.31396 (16)	0.0211 (5)
H91	0.6997 (17)	0.0345 (13)	0.3372 (15)	0.025*
H92	0.6430 (17)	−0.0387 (14)	0.2914 (15)	0.025*
C10	0.58171 (18)	0.06470 (14)	0.23889 (15)	0.0189 (5)
H101	0.6284 (16)	0.0877 (13)	0.1909 (15)	0.023*
H102	0.5226 (16)	0.0385 (13)	0.2052 (15)	0.023*
C11	0.33034 (15)	0.06975 (12)	0.12952 (14)	0.0145 (4)
O12	0.35375 (10)	0.10722 (8)	0.21165 (9)	0.0160 (3)
C13	0.25165 (17)	0.01153 (13)	0.13147 (16)	0.0188 (5)
H13	0.2275 (16)	0.0008 (14)	0.1890 (16)	0.023*
C14	0.21879 (17)	−0.03030 (13)	0.05014 (16)	0.0199 (5)
H14	0.1637 (16)	−0.0666 (14)	0.0540 (15)	0.024*
C15	0.26181 (16)	−0.01498 (13)	−0.03840 (15)	0.0183 (5)
H15	0.2360 (15)	−0.0463 (13)	−0.0936 (15)	0.022*
C16	0.33976 (16)	0.04004 (13)	−0.04243 (15)	0.0163 (5)
H16	0.3683 (15)	0.0523 (13)	−0.1003 (15)	0.020*
C17	0.37838 (15)	0.08255 (12)	0.04054 (14)	0.0139 (4)
C18	0.46758 (15)	0.13478 (12)	0.03271 (13)	0.0139 (4)
C19	0.52757 (18)	0.12788 (14)	−0.05752 (15)	0.0181 (5)
H19A	0.4929 (17)	0.1555 (14)	−0.1079 (16)	0.027*
H19B	0.5293 (16)	0.0748 (15)	−0.0782 (15)	0.027*
H19C	0.5991 (18)	0.1489 (14)	−0.0482 (15)	0.027*
N20	0.49586 (13)	0.18431 (10)	0.10260 (11)	0.0152 (4)
C21	0.58643 (18)	0.23621 (14)	0.09577 (16)	0.0222 (5)
H211	0.5974 (16)	0.2496 (13)	0.0285 (16)	0.027*
H212	0.6468 (18)	0.2055 (14)	0.1226 (16)	0.027*
C22	0.56754 (19)	0.31395 (14)	0.14930 (16)	0.0225 (5)
H221	0.6309 (18)	0.3398 (14)	0.1644 (15)	0.027*
H222	0.5206 (17)	0.3489 (14)	0.1087 (16)	0.027*
N23	0.51726 (13)	0.29409 (10)	0.23916 (12)	0.0166 (4)
C24	0.52723 (16)	0.34161 (13)	0.31422 (15)	0.0188 (5)
C25	0.5844 (2)	0.41992 (15)	0.30703 (19)	0.0263 (6)
H25A	0.652 (2)	0.4135 (16)	0.3180 (17)	0.040*
H25B	0.5622 (18)	0.4579 (16)	0.3546 (18)	0.040*
H25C	0.5750 (18)	0.4459 (16)	0.2461 (18)	0.040*
C26	0.48102 (16)	0.32171 (13)	0.40501 (15)	0.0183 (5)
C27	0.40293 (16)	0.26336 (13)	0.41079 (14)	0.0186 (5)
O28	0.36521 (10)	0.22025 (8)	0.33713 (10)	0.0181 (3)
C29	0.35918 (18)	0.25124 (14)	0.50123 (16)	0.0243 (5)
H29	0.3078 (18)	0.2120 (14)	0.5022 (16)	0.029*
C30	0.3937 (2)	0.29266 (16)	0.58313 (17)	0.0293 (6)
H30	0.3643 (18)	0.2825 (15)	0.6370 (17)	0.035*
C31	0.47268 (19)	0.34752 (16)	0.57808 (17)	0.0295 (6)
H31A	0.4954 (18)	0.3735 (15)	0.6275 (17)	0.035*
C32	0.51534 (19)	0.36198 (14)	0.49171 (17)	0.0253 (5)
H32A	0.5689 (18)	0.3976 (14)	0.4914 (16)	0.030*
Cl1A	0.79066 (4)	0.23619 (3)	0.35925 (4)	0.02212 (13)
O1A	0.80829 (13)	0.30755 (10)	0.30347 (11)	0.0339 (4)
O2A	0.78027 (12)	0.16794 (9)	0.29433 (10)	0.0280 (4)
O3A	0.69829 (12)	0.24462 (11)	0.41007 (12)	0.0357 (4)
O4A	0.87471 (11)	0.22283 (9)	0.42896 (11)	0.0258 (4)
C1A	1.0458 (2)	0.05050 (15)	0.43188 (17)	0.0345 (6)
C11A	1.0945 (3)	0.1044 (2)	0.3592 (2)	0.0499 (8)
H11A	1.171 (2)	0.1142 (19)	0.381 (2)	0.075*
H11B	1.062 (2)	0.152 (2)	0.349 (2)	0.075*
H11C	1.097 (2)	0.080 (2)	0.303 (2)	0.075*
C2A	0.9406 (2)	0.03841 (16)	0.42930 (18)	0.0353 (7)
H2A	0.9032 (19)	0.0658 (16)	0.3855 (18)	0.042*
C3A	0.8953 (2)	−0.01037 (16)	0.49598 (18)	0.0360 (6)
H3A	0.821 (2)	−0.0225 (17)	0.4959 (19)	0.054*

	U11	U22	U33	U12	U13	U23
Co1	0.01606 (16)	0.01228 (14)	0.01440 (14)	−0.00159 (13)	−0.00085 (10)	−0.00040 (12)
N1	0.0193 (10)	0.0172 (9)	0.0218 (9)	−0.0016 (8)	−0.0013 (8)	−0.0006 (8)
C2	0.0290 (15)	0.0167 (12)	0.0376 (14)	0.0002 (11)	−0.0065 (11)	0.0018 (11)
C3	0.0296 (15)	0.0254 (14)	0.0390 (15)	0.0056 (12)	−0.0088 (12)	−0.0012 (12)
C4	0.0247 (16)	0.0319 (16)	0.071 (2)	0.0057 (13)	0.0034 (14)	0.0010 (15)
C5	0.0206 (13)	0.0230 (13)	0.0345 (14)	−0.0013 (11)	−0.0027 (10)	−0.0011 (11)
N6	0.0192 (10)	0.0148 (9)	0.0139 (8)	−0.0019 (8)	0.0011 (7)	0.0001 (7)
C7	0.0265 (13)	0.0202 (12)	0.0155 (11)	0.0007 (10)	0.0025 (9)	0.0029 (9)
C8	0.0314 (15)	0.0224 (13)	0.0244 (12)	0.0030 (11)	0.0029 (11)	0.0035 (10)
C9	0.0213 (13)	0.0178 (12)	0.0241 (12)	0.0052 (10)	0.0005 (9)	0.0011 (10)
C10	0.0207 (13)	0.0190 (12)	0.0172 (11)	0.0033 (10)	0.0020 (9)	−0.0022 (9)
C11	0.0145 (11)	0.0108 (10)	0.0180 (10)	0.0025 (9)	−0.0027 (8)	0.0010 (8)
O12	0.0188 (8)	0.0143 (7)	0.0146 (7)	−0.0036 (6)	−0.0005 (6)	−0.0003 (6)
C13	0.0217 (13)	0.0143 (11)	0.0206 (11)	−0.0019 (10)	0.0025 (9)	0.0020 (9)
C14	0.0150 (12)	0.0133 (11)	0.0308 (12)	−0.0016 (9)	−0.0036 (10)	0.0000 (9)
C15	0.0167 (12)	0.0163 (11)	0.0212 (11)	0.0025 (9)	−0.0076 (9)	−0.0046 (9)
C16	0.0183 (12)	0.0155 (11)	0.0149 (10)	0.0052 (9)	−0.0009 (9)	−0.0002 (9)
C17	0.0131 (11)	0.0109 (10)	0.0175 (10)	0.0011 (9)	−0.0031 (8)	0.0014 (8)
C18	0.0146 (11)	0.0135 (10)	0.0132 (10)	0.0034 (9)	−0.0028 (8)	0.0042 (8)
C19	0.0176 (13)	0.0182 (12)	0.0184 (11)	0.0011 (10)	0.0017 (9)	0.0003 (9)
N20	0.0155 (10)	0.0141 (9)	0.0158 (8)	−0.0024 (7)	−0.0008 (7)	0.0034 (7)
C21	0.0238 (13)	0.0233 (12)	0.0198 (11)	−0.0090 (11)	0.0030 (9)	0.0006 (10)
C22	0.0234 (13)	0.0208 (13)	0.0230 (11)	−0.0091 (10)	−0.0021 (10)	0.0023 (9)
N23	0.0153 (10)	0.0142 (9)	0.0201 (9)	−0.0014 (8)	−0.0024 (7)	0.0007 (8)
C24	0.0134 (12)	0.0159 (11)	0.0262 (12)	0.0032 (9)	−0.0089 (9)	0.0000 (9)
C25	0.0278 (15)	0.0174 (12)	0.0328 (14)	−0.0028 (11)	−0.0080 (11)	−0.0037 (11)
C26	0.0168 (12)	0.0163 (11)	0.0211 (11)	0.0068 (9)	−0.0069 (9)	−0.0041 (9)
C27	0.0175 (12)	0.0192 (11)	0.0186 (10)	0.0094 (10)	−0.0040 (9)	−0.0037 (9)
O28	0.0168 (8)	0.0197 (8)	0.0182 (7)	−0.0001 (6)	0.0032 (6)	−0.0042 (6)
C29	0.0229 (13)	0.0258 (14)	0.0245 (12)	0.0059 (11)	0.0023 (10)	−0.0006 (10)
C30	0.0327 (15)	0.0355 (15)	0.0197 (11)	0.0161 (13)	0.0018 (10)	−0.0028 (11)
C31	0.0308 (15)	0.0316 (15)	0.0250 (13)	0.0136 (12)	−0.0109 (11)	−0.0123 (11)
C32	0.0253 (14)	0.0215 (13)	0.0279 (12)	0.0085 (11)	−0.0110 (10)	−0.0060 (10)
Cl1A	0.0213 (3)	0.0208 (3)	0.0241 (3)	−0.0017 (2)	−0.0004 (2)	−0.0035 (2)
O1A	0.0455 (11)	0.0222 (9)	0.0339 (9)	−0.0021 (8)	−0.0005 (8)	0.0039 (8)
O2A	0.0351 (10)	0.0232 (9)	0.0255 (8)	−0.0091 (8)	−0.0027 (7)	−0.0060 (7)
O3A	0.0208 (9)	0.0498 (12)	0.0366 (10)	0.0078 (9)	0.0044 (7)	−0.0034 (9)
O4A	0.0199 (9)	0.0268 (9)	0.0300 (9)	0.0000 (7)	−0.0069 (7)	−0.0057 (7)
C1A	0.0544 (19)	0.0251 (14)	0.0238 (12)	0.0132 (13)	−0.0004 (12)	−0.0075 (11)
C11A	0.072 (2)	0.0429 (19)	0.0357 (16)	0.0097 (17)	0.0069 (16)	−0.0021 (14)
C2A	0.050 (2)	0.0306 (15)	0.0241 (13)	0.0174 (13)	−0.0091 (12)	−0.0067 (11)
C3A	0.0466 (17)	0.0316 (15)	0.0293 (14)	0.0122 (14)	−0.0020 (12)	−0.0100 (12)

Co1—O12	1.8692 (14)	C17—C18	1.463 (3)
Co1—O28	1.8725 (14)	C18—N20	1.305 (2)
Co1—N23	1.9038 (17)	C18—C19	1.509 (3)
Co1—N20	1.9102 (17)	C19—H19A	0.93 (2)
Co1—N6	2.0168 (17)	C19—H19B	0.92 (2)
Co1—N1	2.0184 (18)	C19—H19C	1.00 (2)
N1—C2	1.485 (3)	N20—C21	1.473 (3)
N1—C5	1.501 (3)	C21—C22	1.510 (3)
N1—H1	0.90 (2)	C21—H211	0.97 (2)
C2—C3	1.518 (3)	C21—H212	1.00 (2)
C2—H21	1.02 (2)	C22—N23	1.469 (3)
C2—H22	1.05 (2)	C22—H221	0.95 (2)
C3—C4	1.494 (4)	C22—H222	1.00 (2)
C3—H31	1.00 (3)	N23—C24	1.301 (3)
C3—H32	0.97 (2)	C24—C26	1.455 (3)
C4—C5	1.538 (4)	C24—C25	1.503 (3)
C4—H41	1.01 (3)	C25—H25A	0.89 (3)
C4—H42	0.94 (3)	C25—H25B	0.96 (3)
C5—H51	0.99 (2)	C25—H25C	0.95 (3)
C5—H52	0.99 (2)	C26—C27	1.413 (3)
N6—C10	1.488 (3)	C26—C32	1.422 (3)
N6—C7	1.501 (3)	C27—O28	1.317 (2)
N6—H6	0.89 (2)	C27—C29	1.413 (3)
C7—C8	1.535 (3)	C29—C30	1.378 (3)
C7—H71	0.95 (2)	C29—H29	0.94 (2)
C7—H72	0.99 (2)	C30—C31	1.382 (4)
C8—C9	1.519 (3)	C30—H30	0.87 (2)
C8—H81	0.97 (2)	C31—C32	1.362 (3)
C8—H82	0.95 (2)	C31—H31A	0.85 (2)
C9—C10	1.515 (3)	C32—H32A	0.92 (2)
C9—H91	1.00 (2)	Cl1A—O1A	1.4343 (16)
C9—H92	0.87 (2)	Cl1A—O3A	1.4365 (16)
C10—H101	1.00 (2)	Cl1A—O4A	1.4428 (15)
C10—H102	0.98 (2)	Cl1A—O2A	1.4433 (15)
C11—O12	1.314 (2)	C1A—C2A	1.393 (4)
C11—C13	1.413 (3)	C1A—C3Ai	1.396 (3)
C11—C17	1.423 (3)	C1A—C11A	1.507 (4)
C13—C14	1.369 (3)	C11A—H11A	1.05 (3)
C13—H13	0.89 (2)	C11A—H11B	0.90 (3)
C14—C15	1.393 (3)	C11A—H11C	0.88 (3)
C14—H14	0.94 (2)	C2A—C3A	1.379 (4)
C15—C16	1.372 (3)	C2A—H2A	0.88 (2)
C15—H15	0.97 (2)	C3A—C1Ai	1.396 (3)
C16—C17	1.415 (3)	C3A—H3A	1.00 (3)
C16—H16	0.92 (2)
O12—Co1—O28	85.80 (6)	C16—C15—C14	119.4 (2)
O12—Co1—N23	177.53 (7)	C16—C15—H15	123.8 (13)
O28—Co1—N23	93.50 (7)	C14—C15—H15	116.7 (13)
O12—Co1—N20	94.02 (7)	C15—C16—C17	122.3 (2)
O28—Co1—N20	176.62 (7)	C15—C16—H16	121.2 (13)
N23—Co1—N20	86.82 (7)	C17—C16—H16	116.5 (13)
O12—Co1—N6	85.96 (7)	C16—C17—C11	117.82 (18)
O28—Co1—N6	91.14 (6)	C16—C17—C18	119.31 (18)
N23—Co1—N6	91.69 (7)	C11—C17—C18	122.82 (17)
N20—Co1—N6	92.21 (7)	N20—C18—C17	121.05 (18)
O12—Co1—N1	91.16 (7)	N20—C18—C19	121.02 (19)
O28—Co1—N1	87.13 (7)	C17—C18—C19	117.91 (18)
N23—Co1—N1	91.17 (7)	C18—C19—H19A	108.8 (14)
N20—Co1—N1	89.50 (7)	C18—C19—H19B	110.4 (14)
N6—Co1—N1	176.75 (8)	H19A—C19—H19B	104.8 (18)
C2—N1—C5	104.47 (18)	C18—C19—H19C	113.0 (12)
C2—N1—Co1	118.08 (14)	H19A—C19—H19C	110.1 (19)
C5—N1—Co1	115.28 (14)	H19B—C19—H19C	109.4 (19)
C2—N1—H1	104.3 (15)	C18—N20—C21	121.32 (17)
C5—N1—H1	100.2 (14)	C18—N20—Co1	127.82 (14)
Co1—N1—H1	112.4 (14)	C21—N20—Co1	110.86 (13)
N1—C2—C3	104.35 (19)	N20—C21—C22	108.25 (19)
N1—C2—H21	113.1 (13)	N20—C21—H211	110.6 (13)
C3—C2—H21	111.7 (13)	C22—C21—H211	107.9 (13)
N1—C2—H22	106.5 (13)	N20—C21—H212	107.9 (13)
C3—C2—H22	107.1 (12)	C22—C21—H212	113.6 (13)
H21—C2—H22	113.4 (18)	H211—C21—H212	108.5 (18)
C4—C3—C2	102.9 (2)	N23—C22—C21	108.23 (18)
C4—C3—H31	110.2 (14)	N23—C22—H221	110.0 (13)
C2—C3—H31	112.9 (13)	C21—C22—H221	109.1 (14)
C4—C3—H32	103.9 (15)	N23—C22—H222	108.2 (13)
C2—C3—H32	109.1 (14)	C21—C22—H222	109.3 (13)
H31—C3—H32	117 (2)	H221—C22—H222	111.9 (19)
C3—C4—C5	105.6 (2)	C24—N23—C22	120.24 (18)
C3—C4—H41	112.7 (16)	C24—N23—Co1	128.10 (15)
C5—C4—H41	113.1 (16)	C22—N23—Co1	111.44 (13)
C3—C4—H42	105.7 (18)	N23—C24—C26	121.16 (19)
C5—C4—H42	109.4 (18)	N23—C24—C25	120.0 (2)
H41—C4—H42	110 (2)	C26—C24—C25	118.8 (2)
N1—C5—C4	106.5 (2)	C24—C25—H25A	112.2 (17)
N1—C5—H51	105.7 (13)	C24—C25—H25B	110.4 (15)
C4—C5—H51	110.2 (14)	H25A—C25—H25B	107 (2)
N1—C5—H52	110.1 (14)	C24—C25—H25C	114.0 (15)
C4—C5—H52	110.9 (14)	H25A—C25—H25C	107 (2)
H51—C5—H52	113.1 (19)	H25B—C25—H25C	106 (2)
C10—N6—C7	104.56 (16)	C27—C26—C32	118.2 (2)
C10—N6—Co1	115.74 (12)	C27—C26—C24	122.51 (18)
C7—N6—Co1	115.66 (14)	C32—C26—C24	119.3 (2)
C10—N6—H6	107.1 (14)	O28—C27—C29	116.7 (2)
C7—N6—H6	107.8 (14)	O28—C27—C26	124.91 (19)
Co1—N6—H6	105.5 (14)	C29—C27—C26	118.33 (19)
N6—C7—C8	106.65 (18)	C27—O28—Co1	124.32 (13)
N6—C7—H71	109.4 (13)	C30—C29—C27	121.4 (2)
C8—C7—H71	111.7 (14)	C30—C29—H29	122.7 (14)
N6—C7—H72	107.1 (13)	C27—C29—H29	115.9 (14)
C8—C7—H72	114.7 (12)	C29—C30—C31	120.1 (2)
H71—C7—H72	107.2 (18)	C29—C30—H30	117.5 (17)
C9—C8—C7	105.97 (19)	C31—C30—H30	122.4 (17)
C9—C8—H81	110.9 (14)	C32—C31—C30	120.1 (2)
C7—C8—H81	110.7 (14)	C32—C31—H31A	118.0 (17)
C9—C8—H82	110.0 (14)	C30—C31—H31A	121.9 (17)
C7—C8—H82	110.3 (14)	C31—C32—C26	121.7 (2)
H81—C8—H82	108.9 (19)	C31—C32—H32A	117.7 (14)
C10—C9—C8	103.04 (18)	C26—C32—H32A	120.5 (14)
C10—C9—H91	108.8 (13)	O1A—Cl1A—O3A	110.12 (11)
C8—C9—H91	108.3 (12)	O1A—Cl1A—O4A	110.17 (10)
C10—C9—H92	112.1 (15)	O3A—Cl1A—O4A	108.98 (9)
C8—C9—H92	113.1 (15)	O1A—Cl1A—O2A	108.95 (9)
H91—C9—H92	111.1 (19)	O3A—Cl1A—O2A	108.82 (10)
N6—C10—C9	105.08 (16)	O4A—Cl1A—O2A	109.78 (10)
N6—C10—H101	109.6 (13)	C2A—C1A—C3Ai	117.5 (2)
C9—C10—H101	114.3 (12)	C2A—C1A—C11A	121.3 (2)
N6—C10—H102	104.8 (13)	C3Ai—C1A—C11A	121.1 (3)
C9—C10—H102	111.9 (13)	C1A—C11A—H11A	109.4 (17)
H101—C10—H102	110.5 (17)	C1A—C11A—H11B	114 (2)
O12—C11—C13	116.42 (18)	H11A—C11A—H11B	111 (3)
O12—C11—C17	125.31 (18)	C1A—C11A—H11C	111 (2)
C13—C11—C17	118.26 (18)	H11A—C11A—H11C	104 (3)
C11—O12—Co1	124.71 (12)	H11B—C11A—H11C	107 (3)
C14—C13—C11	122.0 (2)	C3A—C2A—C1A	121.7 (2)
C14—C13—H13	121.3 (14)	C3A—C2A—H2A	120.9 (17)
C11—C13—H13	116.6 (14)	C1A—C2A—H2A	117.3 (17)
C13—C14—C15	120.0 (2)	C2A—C3A—C1Ai	120.8 (3)
C13—C14—H14	119.1 (13)	C2A—C3A—H3A	124.8 (16)
C15—C14—H14	120.7 (13)	C1Ai—C3A—H3A	114.3 (16)
O12—Co1—N1—C2	151.59 (17)	C19—C18—N20—C21	0.9 (3)
O28—Co1—N1—C2	65.85 (17)	C17—C18—N20—Co1	−0.4 (3)
N23—Co1—N1—C2	−27.59 (17)	C19—C18—N20—Co1	−178.70 (14)
N20—Co1—N1—C2	−114.40 (17)	O12—Co1—N20—C18	14.51 (17)
O12—Co1—N1—C5	27.17 (16)	N23—Co1—N20—C18	−167.82 (18)
O28—Co1—N1—C5	−58.57 (16)	N6—Co1—N20—C18	100.61 (17)
N23—Co1—N1—C5	−152.01 (16)	N1—Co1—N20—C18	−76.62 (17)
N20—Co1—N1—C5	121.18 (16)	O12—Co1—N20—C21	−165.07 (14)
C5—N1—C2—C3	−36.4 (2)	N23—Co1—N20—C21	12.60 (15)
Co1—N1—C2—C3	−166.02 (16)	N6—Co1—N20—C21	−78.97 (15)
N1—C2—C3—C4	40.4 (3)	N1—Co1—N20—C21	103.80 (15)
C2—C3—C4—C5	−28.2 (3)	C18—N20—C21—C22	147.73 (19)
C2—N1—C5—C4	18.5 (3)	Co1—N20—C21—C22	−32.7 (2)
Co1—N1—C5—C4	149.80 (18)	N20—C21—C22—N23	41.1 (2)
C3—C4—C5—N1	6.4 (3)	C21—C22—N23—C24	153.4 (2)
O12—Co1—N6—C10	63.71 (15)	C21—C22—N23—Co1	−31.6 (2)
O28—Co1—N6—C10	149.42 (15)	O28—Co1—N23—C24	9.06 (18)
N23—Co1—N6—C10	−117.05 (15)	N20—Co1—N23—C24	−174.31 (18)
N20—Co1—N6—C10	−30.16 (16)	N6—Co1—N23—C24	−82.19 (18)
O12—Co1—N6—C7	−59.05 (15)	N1—Co1—N23—C24	96.26 (18)
O28—Co1—N6—C7	26.66 (15)	O28—Co1—N23—C22	−165.47 (14)
N23—Co1—N6—C7	120.19 (15)	N20—Co1—N23—C22	11.16 (15)
N20—Co1—N6—C7	−152.92 (15)	N6—Co1—N23—C22	103.28 (15)
C10—N6—C7—C8	21.1 (2)	N1—Co1—N23—C22	−78.27 (15)
Co1—N6—C7—C8	149.59 (15)	C22—N23—C24—C26	−177.86 (19)
N6—C7—C8—C9	2.1 (3)	Co1—N23—C24—C26	8.0 (3)
C7—C8—C9—C10	−24.0 (3)	C22—N23—C24—C25	4.1 (3)
C7—N6—C10—C9	−36.7 (2)	Co1—N23—C24—C25	−169.96 (16)
Co1—N6—C10—C9	−165.17 (14)	N23—C24—C26—C27	−16.8 (3)
C8—C9—C10—N6	37.7 (2)	C25—C24—C26—C27	161.2 (2)
C13—C11—O12—Co1	−166.03 (14)	N23—C24—C26—C32	163.0 (2)
C17—C11—O12—Co1	14.8 (3)	C25—C24—C26—C32	−19.0 (3)
O28—Co1—O12—C11	155.40 (15)	C32—C26—C27—O28	−178.51 (19)
N20—Co1—O12—C11	−21.22 (16)	C24—C26—C27—O28	1.3 (3)
N6—Co1—O12—C11	−113.16 (15)	C32—C26—C27—C29	3.4 (3)
N1—Co1—O12—C11	68.36 (16)	C24—C26—C27—C29	−176.76 (19)
O12—C11—C13—C14	178.56 (19)	C29—C27—O28—Co1	−160.24 (14)
C17—C11—C13—C14	−2.2 (3)	C26—C27—O28—Co1	21.7 (3)
C11—C13—C14—C15	−1.2 (3)	O12—Co1—O28—C27	154.22 (16)
C13—C14—C15—C16	2.4 (3)	N23—Co1—O28—C27	−23.40 (16)
C14—C15—C16—C17	−0.3 (3)	N6—Co1—O28—C27	68.36 (16)
C15—C16—C17—C11	−3.1 (3)	N1—Co1—O28—C27	−114.40 (16)
C15—C16—C17—C18	174.49 (19)	O28—C27—C29—C30	179.3 (2)
O12—C11—C17—C16	−176.63 (18)	C26—C27—C29—C30	−2.4 (3)
C13—C11—C17—C16	4.2 (3)	C27—C29—C30—C31	0.0 (4)
O12—C11—C17—C18	5.9 (3)	C29—C30—C31—C32	1.3 (4)
C13—C11—C17—C18	−173.29 (18)	C30—C31—C32—C26	−0.2 (4)
C16—C17—C18—N20	169.29 (18)	C27—C26—C32—C31	−2.2 (3)
C11—C17—C18—N20	−13.3 (3)	C24—C26—C32—C31	178.0 (2)
C16—C17—C18—C19	−12.4 (3)	C3Ai—C1A—C2A—C3A	0.9 (4)
C11—C17—C18—C19	165.03 (18)	C11A—C1A—C2A—C3A	−179.5 (2)
C17—C18—N20—C21	179.12 (18)	C1A—C2A—C3A—C1Ai	−0.9 (4)

CgA, CgB and CgC are the centroids of the C11-C17, C26–C32 and C1A–C3A,C1A'–C3A' rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4Aii	0.90 (2)	2.32 (2)	3.200 (2)	166.2 (19)
N6—H6···O2A	0.89 (2)	2.55 (2)	3.244 (2)	135.9 (18)
N6—H6···O3A	0.89 (2)	2.33 (2)	3.181 (3)	160.9 (18)
C2A—H2A···O2A	0.88 (2)	2.61 (3)	3.477 (3)	166 (2)
C19—H19B···CgAiii	0.92 (2)	2.85 (2)	3.438 (2)	122.8 (16)
C14—H14···CgBiv	0.94 (2)	2.56 (2)	3.430 (2)	153.8 (17)
C22—H222···CgCv	1.00 (2)	2.92 (2)	3.784 (2)	145.5 (16)

Table 1

Hydrogen-bond geometry (Å, °)

CgA, CgB and CgC are the centroids of the C11–C17, C26–C32 and C1A–C3A,C1A′–C3A′ rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O4Ai	0.90 (2)	2.32 (2)	3.200 (2)	166.2 (19)
N6—H6⋯O2A	0.89 (2)	2.55 (2)	3.244 (2)	135.9 (18)
N6—H6⋯O3A	0.89 (2)	2.33 (2)	3.181 (3)	160.9 (18)
C2A—H2A⋯O2A	0.88 (2)	2.61 (3)	3.477 (3)	166 (2)
C19—H19B⋯CgAii	0.92 (2)	2.85 (2)	3.438 (2)	122.8 (16)
C14—H14⋯CgBiii	0.94 (2)	2.56 (2)	3.430 (2)	153.8 (17)
C22—H222⋯CgCiv	1.00 (2)	2.92 (2)	3.784 (2)	145.5 (16)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .