Dichloridobis(7-amino-2,4-dimethyl-1,8-naphthyridine-κN,N')cobalt(II) methanol disolvate.

The title compound, [CoCl(2)(C(10)H(11)N(3))(2)]·2CH(3)OH, crystallizes with an elongated Co coordination polyhedron in a very distorted octa-hedral geometry. Both naphthyridine ligands coordinate to the Co atom via two N atoms in a bidentate chelating mode. The remaining coordination sites are occupied by two Cl atoms. Two uncoordinated solvent methanol mol-ecules are hydrogen bonded to the Cl atoms. Additional N-H⋯O, C-H⋯Cl and N-H⋯Cl hydrogen bonds, and π-π stacking inter-actions [centroid-centroid distance 3.664 (4) Å], give rise to a three-dimensional network structure.

Related literature

For related literature, see: Bayer (1979 ▶); Che et al. (2001 ▶); Gavrilova & Bosnich (2004 ▶); Harvey et al. (2004 ▶); Jin et al. (2007 ▶); Kukrek et al. (2006 ▶); Mintert & Sheldrick (1995a ▶,b ▶); Oskui et al. (1999 ▶); Oskui & Sheldrick (1999 ▶).

Experimental

Crystal data

[CoCl2(C10H11N3)2]·2CH4O

M = 540.35

Triclinic,

a = 9.694 (3) Å

b = 10.651 (3) Å

c = 14.154 (4) Å

α = 79.523 (4)°

β = 78.548 (4)°

γ = 65.697 (4)°

V = 1297.2 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.90 mm−1

T = 298 (2) K

0.27 × 0.21 × 0.18 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.794, T max = 0.855

6885 measured reflections

4521 independent reflections

2999 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.125

S = 1.04

4521 reflections

300 parameters

H-atom parameters constrained

Δρmax = 0.45 e Å−3

Δρmin = −0.27 e Å−3

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

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680706494X/zl2083sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680706494X/zl2083Isup2.hkl

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

[CoCl2(C10H11N3)2]·2CH4O	Z = 2
Mr = 540.35	F000 = 562
Triclinic, P1	Dx = 1.383 Mg m−3
a = 9.694 (3) Å	Mo Kα radiation λ = 0.71073 Å
b = 10.651 (3) Å	Cell parameters from 2019 reflections
c = 14.154 (4) Å	θ = 2.4–24.7º
α = 79.523 (4)º	µ = 0.90 mm−1
β = 78.548 (4)º	T = 298 (2) K
γ = 65.697 (4)º	Block, violet
V = 1297.2 (6) Å3	0.27 × 0.21 × 0.18 mm

Bruker SMART APEX CCD diffractometer	4521 independent reflections
Radiation source: fine-focus sealed tube	2999 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.021
T = 298(2) K	θmax = 25.0º
phi and ω scans	θmin = 2.1º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −9→11
Tmin = 0.794, Tmax = 0.855	k = −12→12
6885 measured reflections	l = −15→16

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047	H-atom parameters constrained
wR(F2) = 0.125	w = 1/[σ2(Fo2) + (0.0565P)2 + 0.2762P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
4521 reflections	Δρmax = 0.45 e Å−3
300 parameters	Δρmin = −0.27 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq
Co1	0.96112 (6)	0.72223 (5)	0.23994 (3)	0.04516 (18)
Cl1	0.94391 (12)	0.51632 (9)	0.20816 (7)	0.0583 (3)
Cl2	1.22929 (11)	0.63991 (12)	0.21805 (8)	0.0690 (3)
N1	0.9345 (3)	0.9511 (3)	0.2182 (2)	0.0448 (7)
N2	0.8771 (3)	0.8510 (3)	0.1144 (2)	0.0426 (7)
N3	0.8215 (4)	0.7345 (3)	0.0155 (2)	0.0671 (10)
H3A	0.8541	0.6596	0.0544	0.080*
H3B	0.7872	0.7340	−0.0359	0.080*
N4	0.7015 (3)	0.7946 (3)	0.3218 (2)	0.0460 (7)
N5	0.9139 (3)	0.7129 (3)	0.3919 (2)	0.0437 (7)
N6	1.1406 (4)	0.6339 (4)	0.4536 (2)	0.0703 (10)
H6A	1.1885	0.6285	0.3955	0.084*
H6B	1.1906	0.6110	0.5021	0.084*
O1	0.7241 (4)	0.7211 (4)	0.8345 (2)	0.0855 (10)
H1	0.7914	0.6478	0.8186	0.089 (18)*
O2	0.2964 (4)	0.5474 (4)	0.6250 (2)	0.0891 (11)
H2	0.2413	0.5261	0.6713	0.12 (2)*
C1	0.8775 (4)	0.9703 (4)	0.1350 (3)	0.0425 (9)
C2	0.8242 (4)	0.8508 (4)	0.0350 (3)	0.0481 (9)
C3	0.7689 (4)	0.9765 (4)	−0.0293 (3)	0.0545 (10)
H3	0.7321	0.9762	−0.0851	0.065*
C4	0.7702 (4)	1.0942 (4)	−0.0091 (3)	0.0544 (10)
H4	0.7348	1.1748	−0.0513	0.065*
C5	0.8252 (4)	1.0972 (4)	0.0763 (3)	0.0463 (9)
C6	0.8331 (4)	1.2114 (4)	0.1076 (3)	0.0523 (10)
C7	0.8943 (5)	1.1897 (4)	0.1915 (3)	0.0584 (11)
H7	0.9018	1.2636	0.2132	0.070*
C8	0.9459 (4)	1.0583 (4)	0.2454 (3)	0.0492 (9)
C9	0.7767 (5)	1.3537 (4)	0.0519 (3)	0.0749 (13)
H9A	0.7672	1.4213	0.0919	0.112*
H9B	0.6789	1.3739	0.0337	0.112*
H9C	0.8481	1.3564	−0.0053	0.112*
C10	1.0178 (5)	1.0346 (5)	0.3348 (3)	0.0726 (13)
H10A	1.0493	0.9387	0.3603	0.109*
H10B	0.9451	1.0909	0.3824	0.109*
H10C	1.1052	1.0592	0.3189	0.109*
C11	0.7591 (4)	0.7613 (3)	0.4062 (3)	0.0423 (9)
C12	0.9893 (5)	0.6778 (4)	0.4685 (3)	0.0499 (9)
C13	0.9068 (5)	0.6885 (4)	0.5642 (3)	0.0590 (11)
H13	0.9596	0.6616	0.6174	0.071*
C14	0.7540 (5)	0.7371 (4)	0.5777 (3)	0.0593 (11)
H14	0.7017	0.7442	0.6404	0.071*
C15	0.6711 (4)	0.7778 (4)	0.4986 (3)	0.0486 (9)
C16	0.5117 (5)	0.8313 (4)	0.5007 (3)	0.0578 (11)
C17	0.4541 (5)	0.8647 (4)	0.4146 (3)	0.0638 (12)
H17	0.3488	0.9014	0.4149	0.077*
C18	0.5506 (5)	0.8449 (4)	0.3259 (3)	0.0548 (10)
C19	0.4055 (5)	0.8563 (5)	0.5956 (3)	0.0776 (14)
H19A	0.3138	0.9365	0.5854	0.116*
H19B	0.4552	0.8713	0.6423	0.116*
H19C	0.3802	0.7769	0.6192	0.116*
C20	0.4863 (5)	0.8810 (5)	0.2316 (3)	0.0796 (14)
H20A	0.4401	0.9799	0.2175	0.119*
H20B	0.4107	0.8427	0.2367	0.119*
H20C	0.5670	0.8432	0.1804	0.119*
C21	0.5865 (6)	0.7043 (6)	0.8635 (4)	0.1029 (18)
H21A	0.5910	0.6461	0.9241	0.154*
H21B	0.5687	0.6620	0.8152	0.154*
H21C	0.5047	0.7932	0.8712	0.154*
C22	0.4434 (6)	0.4976 (5)	0.6469 (5)	0.107 (2)
H22A	0.5042	0.5342	0.5971	0.161*
H22B	0.4866	0.3982	0.6509	0.161*
H22C	0.4416	0.5256	0.7080	0.161*

	U11	U22	U33	U12	U13	U23
Co1	0.0519 (3)	0.0477 (3)	0.0353 (3)	−0.0186 (2)	−0.0107 (2)	−0.0001 (2)
Cl1	0.0749 (7)	0.0444 (5)	0.0566 (6)	−0.0238 (5)	−0.0118 (5)	−0.0039 (4)
Cl2	0.0498 (6)	0.0887 (8)	0.0553 (6)	−0.0175 (6)	−0.0085 (5)	0.0021 (6)
N1	0.0479 (18)	0.0481 (18)	0.0417 (18)	−0.0220 (15)	−0.0064 (14)	−0.0046 (14)
N2	0.0510 (19)	0.0451 (17)	0.0352 (17)	−0.0225 (15)	−0.0070 (14)	−0.0027 (13)
N3	0.100 (3)	0.064 (2)	0.056 (2)	−0.043 (2)	−0.032 (2)	0.0022 (17)
N4	0.0452 (19)	0.0450 (17)	0.0464 (19)	−0.0159 (15)	−0.0101 (15)	−0.0016 (14)
N5	0.0458 (19)	0.0458 (17)	0.0383 (17)	−0.0171 (15)	−0.0091 (14)	−0.0001 (13)
N6	0.053 (2)	0.103 (3)	0.051 (2)	−0.023 (2)	−0.0185 (17)	−0.004 (2)
O1	0.066 (2)	0.104 (3)	0.074 (2)	−0.010 (2)	−0.0108 (17)	−0.037 (2)
O2	0.066 (2)	0.135 (3)	0.067 (2)	−0.046 (2)	−0.0200 (18)	0.017 (2)
C1	0.042 (2)	0.046 (2)	0.040 (2)	−0.0202 (17)	0.0012 (16)	−0.0053 (17)
C2	0.053 (2)	0.055 (2)	0.041 (2)	−0.027 (2)	−0.0087 (18)	−0.0019 (18)
C3	0.057 (3)	0.067 (3)	0.039 (2)	−0.023 (2)	−0.0149 (18)	−0.0002 (19)
C4	0.057 (3)	0.048 (2)	0.047 (2)	−0.015 (2)	−0.0100 (19)	0.0091 (19)
C5	0.046 (2)	0.046 (2)	0.043 (2)	−0.0183 (18)	−0.0006 (17)	−0.0012 (17)
C6	0.057 (2)	0.043 (2)	0.054 (3)	−0.0209 (19)	0.002 (2)	−0.0043 (18)
C7	0.067 (3)	0.052 (2)	0.062 (3)	−0.029 (2)	0.003 (2)	−0.019 (2)
C8	0.046 (2)	0.057 (2)	0.049 (2)	−0.0237 (19)	−0.0045 (18)	−0.0111 (19)
C9	0.092 (4)	0.047 (2)	0.082 (3)	−0.028 (2)	−0.012 (3)	0.003 (2)
C10	0.078 (3)	0.088 (3)	0.067 (3)	−0.040 (3)	−0.017 (2)	−0.019 (3)
C11	0.050 (2)	0.0359 (19)	0.042 (2)	−0.0175 (17)	−0.0092 (17)	−0.0023 (16)
C12	0.059 (3)	0.049 (2)	0.044 (2)	−0.022 (2)	−0.0132 (19)	−0.0022 (18)
C13	0.077 (3)	0.062 (3)	0.038 (2)	−0.025 (2)	−0.020 (2)	0.0027 (19)
C14	0.076 (3)	0.059 (3)	0.041 (2)	−0.027 (2)	−0.002 (2)	−0.0054 (19)
C15	0.059 (3)	0.043 (2)	0.043 (2)	−0.0211 (19)	−0.0025 (19)	−0.0063 (17)
C16	0.061 (3)	0.052 (2)	0.057 (3)	−0.024 (2)	0.006 (2)	−0.011 (2)
C17	0.043 (2)	0.065 (3)	0.077 (3)	−0.016 (2)	−0.003 (2)	−0.012 (2)
C18	0.054 (3)	0.053 (2)	0.058 (3)	−0.020 (2)	−0.016 (2)	−0.0018 (19)
C19	0.070 (3)	0.082 (3)	0.070 (3)	−0.029 (3)	0.019 (2)	−0.015 (3)
C20	0.066 (3)	0.093 (4)	0.076 (3)	−0.025 (3)	−0.033 (3)	0.010 (3)
C21	0.081 (4)	0.111 (5)	0.113 (5)	−0.030 (3)	−0.013 (3)	−0.024 (4)
C22	0.083 (4)	0.075 (3)	0.168 (6)	−0.034 (3)	−0.036 (4)	0.009 (4)

Co1—N5	2.100 (3)	C7—C8	1.406 (5)
Co1—N2	2.115 (3)	C7—H7	0.9300
Co1—N1	2.312 (3)	C8—C10	1.497 (5)
Co1—Cl2	2.3508 (13)	C9—H9A	0.9600
Co1—Cl1	2.3936 (12)	C9—H9B	0.9600
Co1—N4	2.417 (3)	C9—H9C	0.9600
N1—C8	1.321 (5)	C10—H10A	0.9600
N1—C1	1.345 (4)	C10—H10B	0.9600
N2—C2	1.325 (4)	C10—H10C	0.9600
N2—C1	1.356 (4)	C11—C15	1.409 (5)
N3—C2	1.329 (5)	C12—C13	1.428 (5)
N3—H3A	0.8600	C13—C14	1.339 (6)
N3—H3B	0.8600	C13—H13	0.9300
N4—C18	1.328 (5)	C14—C15	1.408 (5)
N4—C11	1.346 (4)	C14—H14	0.9300
N5—C12	1.339 (5)	C15—C16	1.406 (5)
N5—C11	1.356 (4)	C16—C17	1.368 (6)
N6—C12	1.327 (5)	C16—C19	1.513 (5)
N6—H6A	0.8600	C17—C18	1.401 (5)
N6—H6B	0.8600	C17—H17	0.9300
O1—C21	1.391 (6)	C18—C20	1.505 (6)
O1—H1	0.8200	C19—H19A	0.9600
O2—C22	1.379 (5)	C19—H19B	0.9600
O2—H2	0.8200	C19—H19C	0.9600
C1—C5	1.403 (5)	C20—H20A	0.9600
C2—C3	1.439 (5)	C20—H20B	0.9600
C3—C4	1.341 (5)	C20—H20C	0.9600
C3—H3	0.9300	C21—H21A	0.9600
C4—C5	1.425 (5)	C21—H21B	0.9600
C4—H4	0.9300	C21—H21C	0.9600
C5—C6	1.403 (5)	C22—H22A	0.9600
C6—C7	1.372 (5)	C22—H22B	0.9600
C6—C9	1.507 (5)	C22—H22C	0.9600
N5—Co1—N2	140.51 (11)	C6—C9—H9B	109.5
N5—Co1—N1	94.22 (11)	H9A—C9—H9B	109.5
N2—Co1—N1	60.40 (11)	C6—C9—H9C	109.5
N5—Co1—Cl2	100.61 (9)	H9A—C9—H9C	109.5
N2—Co1—Cl2	109.61 (8)	H9B—C9—H9C	109.5
N1—Co1—Cl2	92.55 (8)	C8—C10—H10A	109.5
N5—Co1—Cl1	103.03 (8)	C8—C10—H10B	109.5
N2—Co1—Cl1	97.99 (8)	H10A—C10—H10B	109.5
N1—Co1—Cl1	158.32 (8)	C8—C10—H10C	109.5
Cl2—Co1—Cl1	96.99 (4)	H10A—C10—H10C	109.5
N5—Co1—N4	58.85 (10)	H10B—C10—H10C	109.5
N2—Co1—N4	88.79 (10)	N4—C11—N5	111.7 (3)
N1—Co1—N4	88.66 (10)	N4—C11—C15	124.9 (3)
Cl2—Co1—N4	159.45 (8)	N5—C11—C15	123.4 (3)
Cl1—Co1—N4	89.14 (8)	N6—C12—N5	118.9 (3)
C8—N1—C1	117.8 (3)	N6—C12—C13	121.1 (4)
C8—N1—Co1	152.4 (3)	N5—C12—C13	119.9 (4)
C1—N1—Co1	89.8 (2)	C14—C13—C12	120.4 (4)
C2—N2—C1	119.8 (3)	C14—C13—H13	119.8
C2—N2—Co1	141.9 (3)	C12—C13—H13	119.8
C1—N2—Co1	98.2 (2)	C13—C14—C15	121.1 (4)
C2—N3—H3A	120.0	C13—C14—H14	119.5
C2—N3—H3B	120.0	C15—C14—H14	119.5
H3A—N3—H3B	120.0	C16—C15—C14	127.9 (4)
C18—N4—C11	117.6 (3)	C16—C15—C11	116.2 (4)
C18—N4—Co1	154.6 (3)	C14—C15—C11	115.9 (4)
C11—N4—Co1	87.8 (2)	C17—C16—C15	118.5 (4)
C12—N5—C11	119.3 (3)	C17—C16—C19	120.5 (4)
C12—N5—Co1	139.0 (3)	C15—C16—C19	120.9 (4)
C11—N5—Co1	101.6 (2)	C16—C17—C18	121.3 (4)
C12—N6—H6A	120.0	C16—C17—H17	119.3
C12—N6—H6B	120.0	C18—C17—H17	119.3
H6A—N6—H6B	120.0	N4—C18—C17	121.5 (4)
C21—O1—H1	109.5	N4—C18—C20	117.6 (4)
C22—O2—H2	109.5	C17—C18—C20	120.9 (4)
N1—C1—N2	111.5 (3)	C16—C19—H19A	109.5
N1—C1—C5	124.7 (3)	C16—C19—H19B	109.5
N2—C1—C5	123.8 (3)	H19A—C19—H19B	109.5
N2—C2—N3	119.8 (3)	C16—C19—H19C	109.5
N2—C2—C3	119.9 (4)	H19A—C19—H19C	109.5
N3—C2—C3	120.3 (3)	H19B—C19—H19C	109.5
C4—C3—C2	120.2 (4)	C18—C20—H20A	109.5
C4—C3—H3	119.9	C18—C20—H20B	109.5
C2—C3—H3	119.9	H20A—C20—H20B	109.5
C3—C4—C5	120.8 (3)	C18—C20—H20C	109.5
C3—C4—H4	119.6	H20A—C20—H20C	109.5
C5—C4—H4	119.6	H20B—C20—H20C	109.5
C1—C5—C6	117.0 (3)	O1—C21—H21A	109.5
C1—C5—C4	115.5 (3)	O1—C21—H21B	109.5
C6—C5—C4	127.5 (3)	H21A—C21—H21B	109.5
C7—C6—C5	117.7 (3)	O1—C21—H21C	109.5
C7—C6—C9	120.5 (4)	H21A—C21—H21C	109.5
C5—C6—C9	121.8 (4)	H21B—C21—H21C	109.5
C6—C7—C8	121.6 (4)	O2—C22—H22A	109.5
C6—C7—H7	119.2	O2—C22—H22B	109.5
C8—C7—H7	119.2	H22A—C22—H22B	109.5
N1—C8—C7	121.2 (4)	O2—C22—H22C	109.5
N1—C8—C10	117.7 (4)	H22A—C22—H22C	109.5
C7—C8—C10	121.1 (4)	H22B—C22—H22C	109.5
C6—C9—H9A	109.5
N5—Co1—N1—C8	32.8 (5)	N3—C2—C3—C4	179.3 (4)
N2—Co1—N1—C8	−179.2 (6)	C2—C3—C4—C5	−0.4 (6)
Cl2—Co1—N1—C8	−68.0 (5)	N1—C1—C5—C6	−0.3 (5)
Cl1—Co1—N1—C8	175.7 (4)	N2—C1—C5—C6	−180.0 (3)
N4—Co1—N1—C8	91.4 (5)	N1—C1—C5—C4	179.6 (3)
N5—Co1—N1—C1	−146.2 (2)	N2—C1—C5—C4	−0.1 (5)
N2—Co1—N1—C1	1.79 (19)	C3—C4—C5—C1	0.6 (5)
Cl2—Co1—N1—C1	112.95 (19)	C3—C4—C5—C6	−179.6 (4)
Cl1—Co1—N1—C1	−3.3 (3)	C1—C5—C6—C7	1.5 (5)
N4—Co1—N1—C1	−87.6 (2)	C4—C5—C6—C7	−178.3 (4)
N5—Co1—N2—C2	−121.2 (4)	C1—C5—C6—C9	−178.5 (3)
N1—Co1—N2—C2	−177.4 (4)	C4—C5—C6—C9	1.7 (6)
Cl2—Co1—N2—C2	101.1 (4)	C5—C6—C7—C8	−0.8 (6)
Cl1—Co1—N2—C2	0.7 (4)	C9—C6—C7—C8	179.2 (4)
N4—Co1—N2—C2	−88.3 (4)	C1—N1—C8—C7	2.6 (5)
N5—Co1—N2—C1	54.4 (3)	Co1—N1—C8—C7	−176.3 (4)
N1—Co1—N2—C1	−1.79 (19)	C1—N1—C8—C10	−176.5 (3)
Cl2—Co1—N2—C1	−83.3 (2)	Co1—N1—C8—C10	4.6 (7)
Cl1—Co1—N2—C1	176.32 (19)	C6—C7—C8—N1	−1.4 (6)
N4—Co1—N2—C1	87.4 (2)	C6—C7—C8—C10	177.7 (4)
N5—Co1—N4—C18	178.9 (6)	C18—N4—C11—N5	−179.3 (3)
N2—Co1—N4—C18	22.7 (6)	Co1—N4—C11—N5	0.3 (3)
N1—Co1—N4—C18	83.1 (6)	C18—N4—C11—C15	−1.1 (5)
Cl2—Co1—N4—C18	176.8 (5)	Co1—N4—C11—C15	178.5 (3)
Cl1—Co1—N4—C18	−75.3 (6)	C12—N5—C11—N4	178.6 (3)
N5—Co1—N4—C11	−0.21 (19)	Co1—N5—C11—N4	−0.4 (3)
N2—Co1—N4—C11	−156.4 (2)	C12—N5—C11—C15	0.4 (5)
N1—Co1—N4—C11	−96.0 (2)	Co1—N5—C11—C15	−178.6 (3)
Cl2—Co1—N4—C11	−2.3 (3)	C11—N5—C12—N6	−178.3 (3)
Cl1—Co1—N4—C11	105.60 (19)	Co1—N5—C12—N6	0.1 (6)
N2—Co1—N5—C12	−138.9 (3)	C11—N5—C12—C13	1.4 (5)
N1—Co1—N5—C12	−92.5 (4)	Co1—N5—C12—C13	179.8 (3)
Cl2—Co1—N5—C12	0.9 (4)	N6—C12—C13—C14	177.9 (4)
Cl1—Co1—N5—C12	100.7 (4)	N5—C12—C13—C14	−1.8 (6)
N4—Co1—N5—C12	−178.4 (4)	C12—C13—C14—C15	0.4 (6)
N2—Co1—N5—C11	39.7 (3)	C13—C14—C15—C16	−179.6 (4)
N1—Co1—N5—C11	86.1 (2)	C13—C14—C15—C11	1.2 (6)
Cl2—Co1—N5—C11	179.49 (19)	N4—C11—C15—C16	1.0 (5)
Cl1—Co1—N5—C11	−80.7 (2)	N5—C11—C15—C16	179.0 (3)
N4—Co1—N5—C11	0.22 (19)	N4—C11—C15—C14	−179.6 (3)
C8—N1—C1—N2	177.9 (3)	N5—C11—C15—C14	−1.7 (5)
Co1—N1—C1—N2	−2.6 (3)	C14—C15—C16—C17	179.9 (4)
C8—N1—C1—C5	−1.8 (5)	C11—C15—C16—C17	−0.9 (5)
Co1—N1—C1—C5	177.6 (3)	C14—C15—C16—C19	2.1 (6)
C2—N2—C1—N1	179.8 (3)	C11—C15—C16—C19	−178.7 (3)
Co1—N2—C1—N1	2.9 (3)	C15—C16—C17—C18	0.9 (6)
C2—N2—C1—C5	−0.5 (5)	C19—C16—C17—C18	178.7 (4)
Co1—N2—C1—C5	−177.4 (3)	C11—N4—C18—C17	0.9 (5)
C1—N2—C2—N3	−178.9 (3)	Co1—N4—C18—C17	−178.0 (4)
Co1—N2—C2—N3	−3.9 (6)	C11—N4—C18—C20	−179.5 (4)
C1—N2—C2—C3	0.7 (5)	Co1—N4—C18—C20	1.6 (8)
Co1—N2—C2—C3	175.7 (3)	C16—C17—C18—N4	−0.9 (6)
N2—C2—C3—C4	−0.2 (6)	C16—C17—C18—C20	179.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···Cl1i	0.82	2.35	3.162 (4)	172
O1—H1···Cl1ii	0.82	2.44	3.194 (4)	154
N6—H6B···O2iii	0.86	2.06	2.918 (4)	175
N6—H6A···Cl2	0.86	2.45	3.269 (4)	159
N3—H3B···O1iv	0.86	2.09	2.947 (4)	175
N3—H3A···Cl1	0.86	2.51	3.309 (3)	156
C22—H22B···C17i	0.96	2.91	3.789 (7)	154
C22—H22B···C18i	0.96	2.71	3.575 (6)	150
C4—H4···Cl2v	0.93	2.85	3.705 (4)	153
C7—H7···Cl1vi	0.93	2.87	3.757 (4)	160
C13—H13···Cl1ii	0.93	2.88	3.733 (4)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯Cl1i	0.82	2.35	3.162 (4)	172
O1—H1⋯Cl1ii	0.82	2.44	3.194 (4)	154
N6—H6B⋯O2iii	0.86	2.06	2.918 (4)	175
N6—H6A⋯Cl2	0.86	2.45	3.269 (4)	159
N3—H3B⋯O1iv	0.86	2.09	2.947 (4)	175
N3—H3A⋯Cl1	0.86	2.51	3.309 (3)	156
C22—H22B⋯C17i	0.96	2.91	3.789 (7)	154
C22—H22B⋯C18i	0.96	2.71	3.575 (6)	150
C4—H4⋯Cl2v	0.93	2.85	3.705 (4)	153
C7—H7⋯Cl1vi	0.93	2.87	3.757 (4)	160
C13—H13⋯Cl1ii	0.93	2.88	3.733 (4)	152

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