Two different one-dimensional supra­molecular chains formed from the reaction of 2-[1-(pyridin-4-ylmethyl)-1H-benzimidazol-2-yl]quinoline with two different precursors, Co(NO₃)₂ and CoCl₂

Two different one-dimensional supra­molecular chains with Co^II cations have been synthesized based on the semi-rigid ligand 2-[1-(pyridin-4-ylmethyl)-1H-benzimidazol-2-yl]quinoline (L), obtained by condensation of 2-(1H-benzimidazol-2-yl)quinoline and 4-(chloro­methyl)pyridine hydro­chloride. Starting from different Co^II salts, two new compounds have been obtained, viz. catena-poly[[[dinitrato­cobalt(II)]-μ-2-[1-(pyridin-4-ylmethyl)-1H-benzimidazol-2-yl]quinoline] di­chloro­methane mono­solvate aceto­nitrile mono­solvate], {[Co(NO₃)₂(C₂₂H₁₆N₄)]·CH₂Cl₂·CH₃CN}_n, (I) and catena-poly[[[di­chlorido­cobalt(II)]-μ-2-[1-(pyridin-4-ylmethyl)-1H-benz­imidazol-2-yl]quinoline] methanol disolvate], {[CoCl₂(C₂₂H₁₆N₄)]·2CH₃OH}_n, (II). In (I), the Co^II centres lie in a distorted octa­hedral [CoN₃O₃] coordination environment. {Co(NO₃)₂L}_n units form one-dimensional helical chains, where the L ligand has different directions of twist. The helical chains stack together via inter­chain π–π inter­actions to form a two-dimensional sheet, and another type of π–π inter­action further connects neighbouring sheets into a three-dimensional framework with hexa­gonal channels, in which the aceto­nitrile mol­ecules and disordered di­chloro­methane mol­ecules are located. In (II), the Co^II centres lie in a distorted trigonal–bipyramidal [CoCl₂N₃] coordination environment. {CoCl₂L}_n units form one-dimensional chains. The chains inter­act via C—H...π and C—H...Cl inter­actions. The result is that two-dimensional sheets are generated, which are further linked into a three-dimensional framework via inter­layer C—H...Cl inter­actions. When viewed down the crystallographic b axis, the methanol solvent mol­ecules are located in an orderly manner in wave-like channels.

Computing details

For both structures, data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO (Agilent, 2013); data reduction: CrysAlis PRO (Agilent, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

catena-Poly[[[dinitratocobalt(II)]-µ-2-[1-(pyridin-4-ylmethyl)-1H-benzimidazol-2-yl]quinoline] dichloromethane monosolvate acetonitrile monosolvate] (I)

Crystal data

[Co(NO3)2(C22H16N4)]·CH2Cl2·C2H3N	F(000) = 1316
Mr = 645.32	Dx = 1.606 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P2yn	Cell parameters from 4115 reflections
a = 10.3883 (5) Å	θ = 3.4–28.3°
b = 15.8826 (8) Å	µ = 0.90 mm^−1
c = 16.3309 (12) Å	T = 141 K
β = 97.949 (6)°	Plate, clear light red
V = 2668.6 (3) Å^3	0.26 × 0.17 × 0.03 mm
Z = 4

Data collection

Agilent SuperNova Dual diffractometer (Cu at zero) with Eos detector	5444 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	4354 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.038
Detector resolution: 16.0793 pixels mm^-1	θmax = 26.4°, θmin = 3.2°
ω scans	h = −12→12
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	k = −14→19
Tmin = 0.800, Tmax = 0.974	l = −16→20
11856 measured reflections

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)] = 0.073	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.201	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0864P)^2 + 11.4352P] where P = (Fo^2 + 2Fc^2)/3
5444 reflections	(Δ/σ)max < 0.001
390 parameters	Δρmax = 0.67 e Å^−3
35 restraints	Δρmin = −1.24 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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.6154 (5)	0.8739 (3)	0.4232 (3)	0.0337 (11)
H1	0.5950	0.8216	0.3991	0.040*
C2	0.6709 (6)	0.8782 (4)	0.5029 (4)	0.0458 (14)
H2	0.6875	0.8289	0.5334	0.055*
C3	0.7035 (6)	0.9558 (4)	0.5400 (4)	0.0496 (15)
H3	0.7428	0.9572	0.5947	0.060*
C4	0.6801 (5)	1.0281 (4)	0.4994 (4)	0.0419 (13)
H4	0.7023	1.0789	0.5259	0.050*
C5	0.6205 (5)	1.0276 (3)	0.4144 (3)	0.0357 (11)
C6	0.5879 (4)	0.9480 (3)	0.3757 (3)	0.0255 (9)
C7	0.5082 (4)	1.0143 (3)	0.2524 (3)	0.0225 (9)
C8	0.5385 (5)	1.0942 (3)	0.2877 (3)	0.0328 (11)
H8	0.5190	1.1425	0.2564	0.039*
C9	0.5955 (5)	1.1007 (3)	0.3667 (3)	0.0378 (12)
H9	0.6181	1.1532	0.3894	0.045*
C10	0.4492 (4)	1.0006 (3)	0.1659 (3)	0.0203 (8)
C11	0.3696 (4)	0.9251 (3)	0.0581 (3)	0.0203 (8)
C12	0.3268 (4)	0.8603 (3)	0.0039 (3)	0.0288 (10)
H12	0.3352	0.8039	0.0192	0.035*
C13	0.2700 (5)	0.8855 (3)	−0.0754 (3)	0.0355 (11)
H13	0.2395	0.8449	−0.1143	0.043*
C14	0.2584 (5)	0.9716 (3)	−0.0971 (3)	0.0325 (11)
H14	0.2218	0.9860	−0.1504	0.039*
C15	0.2993 (5)	1.0349 (3)	−0.0422 (3)	0.0313 (10)
H15	0.2905	1.0914	−0.0568	0.038*
C16	0.3539 (4)	1.0099 (3)	0.0354 (3)	0.0259 (10)
C17	0.4078 (5)	1.1488 (3)	0.1060 (3)	0.0285 (10)
H29A	0.3978	1.1684	0.0492	0.034*
H29B	0.4919	1.1677	0.1329	0.034*
C18	0.3033 (4)	1.1884 (3)	0.1489 (3)	0.0270 (10)
C19	0.3007 (5)	1.2760 (3)	0.1548 (4)	0.0403 (13)
H19	0.3626	1.3085	0.1334	0.048*
C20	0.2055 (5)	1.3136 (3)	0.1926 (4)	0.0420 (14)
H20	0.2051	1.3721	0.1965	0.050*
C21	0.1160 (5)	1.1861 (3)	0.2190 (3)	0.0330 (11)
H21	0.0536	1.1550	0.2415	0.040*
C22	0.2080 (5)	1.1440 (3)	0.1816 (3)	0.0329 (11)
H22	0.2059	1.0855	0.1783	0.039*
C23	0.4787 (7)	0.3707 (4)	0.3957 (4)	0.080 (2)	0.50
H23A	0.5398	0.3716	0.3558	0.095*	0.50
H23B	0.3965	0.3479	0.3696	0.095*	0.50
C24	0.4779 (5)	0.4782 (3)	0.1854 (4)	0.0365 (12)
C25	0.5698 (6)	0.4773 (4)	0.1274 (4)	0.0524 (15)
H25A	0.5637	0.4247	0.0981	0.079*
H25B	0.6560	0.4839	0.1564	0.079*
H25C	0.5510	0.5227	0.0888	0.079*
C23'	0.4787 (7)	0.3707 (4)	0.3957 (4)	0.080 (2)	0.50
H23C	0.4319	0.4210	0.4078	0.095*	0.50
H23D	0.5445	0.3842	0.3610	0.095*	0.50
Cl1	0.5423 (3)	0.3112 (2)	0.4879 (3)	0.1438 (14)	0.50
Cl2	0.4585 (5)	0.4744 (3)	0.4383 (4)	0.1009 (16)	0.50
Cl1'	0.5423 (3)	0.3112 (2)	0.4879 (3)	0.1438 (14)	0.50
Cl2'	0.3725 (5)	0.2856 (3)	0.3549 (3)	0.0859 (13)	0.50
Co1	0.52445 (5)	0.82969 (3)	0.21321 (4)	0.0217 (2)
N1	0.3870 (4)	0.7703 (2)	0.2757 (3)	0.0342 (10)
N2	0.4059 (3)	1.0572 (2)	0.1060 (2)	0.0236 (8)
N3	0.4298 (3)	0.9215 (2)	0.1395 (2)	0.0211 (7)
N4	0.5337 (3)	0.9427 (2)	0.2945 (2)	0.0236 (8)
N5	0.7683 (4)	0.7988 (2)	0.2560 (2)	0.0278 (8)
N6	0.5631 (4)	0.7148 (2)	0.0741 (2)	0.0320 (9)
N7	0.4037 (5)	0.4788 (3)	0.2305 (4)	0.0547 (14)
O4	0.6795 (3)	0.7490 (2)	0.2714 (2)	0.0311 (7)
O5	0.8846 (3)	0.7838 (2)	0.2750 (3)	0.0436 (10)
O6	0.7295 (3)	0.86669 (19)	0.2194 (2)	0.0286 (7)
O1	0.4899 (4)	0.7315 (2)	0.1273 (2)	0.0318 (9)	0.844 (5)
O2	0.5320 (5)	0.6623 (3)	0.0197 (3)	0.0525 (14)	0.844 (5)
O3	0.6691 (4)	0.7540 (3)	0.0768 (3)	0.0424 (11)	0.844 (5)
O1'	0.5906 (18)	0.7869 (7)	0.0987 (12)	0.0318 (9)	0.156 (5)
O2'	0.613 (3)	0.6823 (12)	0.0164 (13)	0.0525 (14)	0.156 (5)
O3'	0.4761 (18)	0.6742 (11)	0.1044 (13)	0.0424 (11)	0.156 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.032 (3)	0.034 (3)	0.036 (3)	0.004 (2)	0.007 (2)	0.005 (2)
C2	0.043 (3)	0.055 (4)	0.040 (3)	0.005 (3)	0.007 (2)	0.011 (3)
C3	0.040 (3)	0.073 (4)	0.037 (3)	−0.008 (3)	0.006 (2)	0.001 (3)
C4	0.034 (3)	0.050 (3)	0.042 (3)	−0.011 (2)	0.008 (2)	−0.017 (3)
C5	0.031 (3)	0.036 (3)	0.042 (3)	−0.004 (2)	0.012 (2)	−0.004 (2)
C6	0.021 (2)	0.027 (2)	0.030 (2)	−0.0006 (17)	0.0091 (18)	−0.0025 (19)
C7	0.017 (2)	0.021 (2)	0.031 (2)	0.0011 (16)	0.0078 (17)	−0.0013 (18)
C8	0.029 (2)	0.027 (2)	0.042 (3)	−0.0002 (19)	0.001 (2)	−0.009 (2)
C9	0.040 (3)	0.026 (2)	0.048 (3)	−0.008 (2)	0.006 (2)	−0.010 (2)
C10	0.0146 (19)	0.019 (2)	0.028 (2)	−0.0013 (15)	0.0083 (16)	−0.0009 (17)
C11	0.0159 (19)	0.019 (2)	0.027 (2)	−0.0001 (15)	0.0076 (16)	−0.0002 (17)
C12	0.024 (2)	0.024 (2)	0.039 (3)	−0.0019 (18)	0.0070 (19)	−0.007 (2)
C13	0.031 (3)	0.039 (3)	0.038 (3)	−0.006 (2)	0.008 (2)	−0.016 (2)
C14	0.028 (2)	0.041 (3)	0.030 (2)	0.001 (2)	0.0076 (19)	0.002 (2)
C15	0.026 (2)	0.030 (2)	0.039 (3)	0.0007 (19)	0.010 (2)	0.000 (2)
C16	0.018 (2)	0.025 (2)	0.037 (3)	0.0018 (17)	0.0111 (18)	−0.0024 (19)
C17	0.028 (2)	0.018 (2)	0.040 (3)	−0.0004 (18)	0.010 (2)	0.0006 (19)
C18	0.023 (2)	0.023 (2)	0.035 (3)	−0.0004 (17)	0.0047 (19)	−0.0003 (19)
C19	0.031 (3)	0.021 (2)	0.072 (4)	−0.002 (2)	0.019 (3)	0.002 (2)
C20	0.035 (3)	0.021 (2)	0.074 (4)	0.000 (2)	0.023 (3)	−0.002 (2)
C21	0.032 (3)	0.019 (2)	0.052 (3)	−0.0010 (19)	0.019 (2)	0.002 (2)
C22	0.037 (3)	0.014 (2)	0.051 (3)	−0.0013 (19)	0.016 (2)	−0.001 (2)
C23	0.070 (5)	0.103 (7)	0.068 (5)	−0.016 (5)	0.018 (4)	−0.013 (5)
C24	0.033 (3)	0.026 (2)	0.049 (3)	0.002 (2)	0.001 (2)	−0.004 (2)
C25	0.047 (3)	0.050 (4)	0.065 (4)	0.009 (3)	0.021 (3)	0.007 (3)
C23'	0.070 (5)	0.103 (7)	0.068 (5)	−0.016 (5)	0.018 (4)	−0.013 (5)
Cl1	0.0856 (19)	0.141 (3)	0.215 (4)	−0.0029 (19)	0.056 (2)	0.042 (3)
Cl2	0.072 (3)	0.090 (3)	0.148 (5)	−0.005 (2)	0.043 (3)	−0.014 (3)
Cl1'	0.0856 (19)	0.141 (3)	0.215 (4)	−0.0029 (19)	0.056 (2)	0.042 (3)
Cl2'	0.092 (3)	0.090 (3)	0.077 (3)	0.007 (3)	0.018 (2)	−0.007 (2)
Co1	0.0189 (3)	0.0144 (3)	0.0331 (4)	0.0000 (2)	0.0077 (2)	0.0021 (2)
N1	0.028 (2)	0.0171 (18)	0.061 (3)	0.0003 (16)	0.019 (2)	0.0052 (18)
N2	0.0203 (18)	0.0203 (18)	0.031 (2)	0.0018 (14)	0.0066 (15)	0.0014 (15)
N3	0.0194 (17)	0.0152 (16)	0.0295 (19)	−0.0032 (13)	0.0060 (14)	−0.0014 (14)
N4	0.0213 (18)	0.0232 (19)	0.0271 (19)	0.0004 (15)	0.0060 (15)	0.0016 (15)
N5	0.028 (2)	0.0225 (19)	0.033 (2)	0.0062 (16)	0.0030 (16)	0.0028 (16)
N6	0.040 (2)	0.0212 (19)	0.036 (2)	0.0054 (17)	0.0097 (18)	0.0022 (17)
N7	0.054 (3)	0.031 (3)	0.083 (4)	0.007 (2)	0.023 (3)	−0.006 (3)
O4	0.0294 (17)	0.0264 (17)	0.0384 (19)	0.0025 (14)	0.0079 (14)	0.0097 (14)
O5	0.0254 (18)	0.035 (2)	0.068 (3)	0.0097 (15)	−0.0009 (17)	0.0047 (19)
O6	0.0273 (17)	0.0196 (15)	0.0393 (19)	0.0058 (13)	0.0056 (14)	0.0058 (14)
O1	0.032 (2)	0.024 (2)	0.041 (2)	0.0039 (16)	0.0093 (17)	−0.0060 (16)
O2	0.076 (4)	0.033 (3)	0.052 (3)	−0.008 (2)	0.020 (3)	−0.018 (2)
O3	0.045 (3)	0.039 (2)	0.045 (3)	−0.007 (2)	0.016 (2)	0.005 (2)
O1'	0.032 (2)	0.024 (2)	0.041 (2)	0.0039 (16)	0.0093 (17)	−0.0060 (16)
O2'	0.076 (4)	0.033 (3)	0.052 (3)	−0.008 (2)	0.020 (3)	−0.018 (2)
O3'	0.045 (3)	0.039 (2)	0.045 (3)	−0.007 (2)	0.016 (2)	0.005 (2)

Geometric parameters (Å, º)

C1—C2	1.351 (8)	C18—C19	1.396 (7)
C1—C6	1.417 (7)	C19—C20	1.373 (7)
C1—H1	0.9300	C19—H19	0.9300
C2—C3	1.395 (9)	C20—N1^i	1.342 (6)
C2—H2	0.9300	C20—H20	0.9300
C3—C4	1.331 (9)	C21—N1^i	1.341 (6)
C3—H3	0.9300	C21—C22	1.377 (7)
C4—C5	1.439 (8)	C21—H21	0.9300
C4—H4	0.9300	C22—H22	0.9300
C5—C9	1.402 (8)	C23—Cl2	1.812 (7)
C5—C6	1.433 (7)	C23—Cl1	1.823 (6)
C6—N4	1.370 (6)	C23—H23A	0.9700
C7—N4	1.336 (6)	C23—H23B	0.9700
C7—C8	1.411 (6)	C24—N7	1.137 (8)
C7—C10	1.477 (6)	C24—C25	1.435 (8)
C8—C9	1.346 (7)	C25—H25A	0.9600
C8—H8	0.9300	C25—H25B	0.9600
C9—H9	0.9300	C25—H25C	0.9600
C10—N3	1.335 (5)	Cl2—Cl2^ii	2.232 (12)
C10—N2	1.358 (6)	Co1—N3	2.053 (4)
C11—C12	1.389 (6)	Co1—N1	2.091 (4)
C11—N3	1.390 (6)	Co1—O1	2.096 (4)
C11—C16	1.401 (6)	Co1—O4	2.172 (3)
C12—C13	1.405 (7)	Co1—O1'	2.187 (15)
C12—H12	0.9300	Co1—O6	2.199 (3)
C13—C14	1.413 (7)	Co1—N4	2.226 (4)
C13—H13	0.9300	N1—C21^iii	1.341 (6)
C14—C15	1.374 (7)	N1—C20^iii	1.342 (6)
C14—H14	0.9300	N5—O5	1.228 (5)
C15—C16	1.373 (7)	N5—O4	1.266 (5)
C15—H15	0.9300	N5—O6	1.271 (5)
C16—N2	1.419 (6)	N6—O2	1.229 (5)
C17—N2	1.454 (6)	N6—O1'	1.234 (7)
C17—C18	1.509 (6)	N6—O2'	1.246 (7)
C17—H29A	0.9700	N6—O1	1.259 (4)
C17—H29B	0.9700	N6—O3	1.260 (5)
C18—C22	1.382 (7)	N6—O3'	1.265 (7)
C2—C1—C6	120.8 (5)	Cl2—C23—Cl1	101.6 (4)
C2—C1—H1	119.6	Cl2—C23—H23A	111.4
C6—C1—H1	119.6	Cl1—C23—H23A	111.4
C1—C2—C3	120.6 (6)	Cl2—C23—H23B	111.4
C1—C2—H2	119.7	Cl1—C23—H23B	111.4
C3—C2—H2	119.7	H23A—C23—H23B	109.3
C4—C3—C2	121.9 (5)	N7—C24—C25	179.0 (7)
C4—C3—H3	119.0	C24—C25—H25A	109.5
C2—C3—H3	119.0	C24—C25—H25B	109.5
C3—C4—C5	120.0 (5)	H25A—C25—H25B	109.5
C3—C4—H4	120.0	C24—C25—H25C	109.5
C5—C4—H4	120.0	H25A—C25—H25C	109.5
C9—C5—C6	118.1 (5)	H25B—C25—H25C	109.5
C9—C5—C4	123.6 (5)	C23—Cl2—Cl2^ii	128.9 (5)
C6—C5—C4	118.3 (5)	N3—Co1—N1	107.58 (15)
N4—C6—C1	120.2 (4)	N3—Co1—O1	96.45 (15)
N4—C6—C5	121.5 (4)	N1—Co1—O1	85.74 (16)
C1—C6—C5	118.3 (4)	N3—Co1—O4	160.35 (13)
N4—C7—C8	122.5 (4)	N1—Co1—O4	92.06 (14)
N4—C7—C10	113.2 (4)	O1—Co1—O4	84.35 (14)
C8—C7—C10	124.3 (4)	N3—Co1—O1'	84.3 (5)
C9—C8—C7	120.3 (5)	N1—Co1—O1'	126.4 (3)
C9—C8—H8	119.9	O1—Co1—O1'	40.7 (3)
C7—C8—H8	119.9	O4—Co1—O1'	83.6 (6)
C8—C9—C5	119.5 (5)	N3—Co1—O6	102.71 (13)
C8—C9—H9	120.3	N1—Co1—O6	145.16 (16)
C5—C9—H9	120.3	O1—Co1—O6	107.76 (13)
N3—C10—N2	111.8 (4)	O4—Co1—O6	58.80 (12)
N3—C10—C7	118.1 (4)	O1'—Co1—O6	72.9 (4)
N2—C10—C7	130.1 (4)	N3—Co1—N4	75.81 (14)
C12—C11—N3	129.8 (4)	N1—Co1—N4	92.78 (15)
C12—C11—C16	121.9 (4)	O1—Co1—N4	171.31 (15)
N3—C11—C16	108.2 (4)	O4—Co1—N4	104.27 (13)
C11—C12—C13	115.6 (4)	O1'—Co1—N4	140.1 (3)
C11—C12—H12	122.2	O6—Co1—N4	78.19 (13)
C13—C12—H12	122.2	C21^iii—N1—C20^iii	117.5 (4)
C12—C13—C14	121.1 (5)	C21^iii—N1—Co1	120.3 (3)
C12—C13—H13	119.4	C20^iii—N1—Co1	122.1 (3)
C14—C13—H13	119.4	C10—N2—C16	106.5 (4)
C15—C14—C13	122.4 (5)	C10—N2—C17	131.2 (4)
C15—C14—H14	118.8	C16—N2—C17	122.2 (4)
C13—C14—H14	118.8	C10—N3—C11	107.3 (4)
C16—C15—C14	116.2 (5)	C10—N3—Co1	116.2 (3)
C16—C15—H15	121.9	C11—N3—Co1	134.9 (3)
C14—C15—H15	121.9	C7—N4—C6	118.1 (4)
C15—C16—C11	122.6 (4)	C7—N4—Co1	113.0 (3)
C15—C16—N2	131.2 (4)	C6—N4—Co1	127.3 (3)
C11—C16—N2	106.1 (4)	O5—N5—O4	123.1 (4)
N2—C17—C18	114.0 (4)	O5—N5—O6	121.4 (4)
N2—C17—H29A	108.8	O4—N5—O6	115.5 (4)
C18—C17—H29A	108.8	O2—N6—O1'	153.0 (10)
N2—C17—H29B	108.8	O2—N6—O2'	42.9 (10)
C18—C17—H29B	108.8	O1'—N6—O2'	122.0 (7)
H29A—C17—H29B	107.6	O2—N6—O1	121.2 (4)
C22—C18—C19	117.5 (4)	O1'—N6—O1	73.4 (8)
C22—C18—C17	124.5 (4)	O2'—N6—O1	163.9 (9)
C19—C18—C17	118.0 (4)	O2—N6—O3	120.1 (4)
C20—C19—C18	119.1 (5)	O1'—N6—O3	50.9 (8)
C20—C19—H19	120.4	O2'—N6—O3	77.3 (10)
C18—C19—H19	120.4	O1—N6—O3	118.7 (4)
N1^i—C20—C19	123.3 (5)	O2—N6—O3'	78.8 (9)
N1^i—C20—H20	118.3	O1'—N6—O3'	119.4 (7)
C19—C20—H20	118.3	O2'—N6—O3'	118.5 (7)
N1^i—C21—C22	122.5 (4)	O1—N6—O3'	46.0 (8)
N1^i—C21—H21	118.8	O3—N6—O3'	154.9 (11)
C22—C21—H21	118.8	N5—O4—Co1	93.5 (2)
C21—C22—C18	120.1 (4)	N5—O6—Co1	92.1 (2)
C21—C22—H22	120.0	N6—O1—Co1	123.7 (3)
C18—C22—H22	120.0	N6—O1'—Co1	118.7 (10)
C6—C1—C2—C3	−0.7 (8)	N1—Co1—N3—C10	104.7 (3)
C1—C2—C3—C4	1.0 (9)	O1—Co1—N3—C10	−167.8 (3)
C2—C3—C4—C5	−0.6 (9)	O4—Co1—N3—C10	−76.5 (5)
C3—C4—C5—C9	−178.4 (5)	O1'—Co1—N3—C10	−128.9 (5)
C3—C4—C5—C6	0.0 (8)	O6—Co1—N3—C10	−57.9 (3)
C2—C1—C6—N4	178.8 (5)	N4—Co1—N3—C10	16.3 (3)
C2—C1—C6—C5	0.1 (7)	N1—Co1—N3—C11	−92.1 (4)
C9—C5—C6—N4	0.0 (7)	O1—Co1—N3—C11	−4.6 (4)
C4—C5—C6—N4	−178.5 (4)	O4—Co1—N3—C11	86.7 (6)
C9—C5—C6—C1	178.7 (5)	O1'—Co1—N3—C11	34.3 (5)
C4—C5—C6—C1	0.3 (7)	O6—Co1—N3—C11	105.3 (4)
N4—C7—C8—C9	0.1 (7)	N4—Co1—N3—C11	179.5 (4)
C10—C7—C8—C9	−178.2 (4)	C8—C7—N4—C6	2.0 (6)
C7—C8—C9—C5	−2.1 (8)	C10—C7—N4—C6	−179.6 (3)
C6—C5—C9—C8	2.1 (8)	C8—C7—N4—Co1	−164.3 (3)
C4—C5—C9—C8	−179.6 (5)	C10—C7—N4—Co1	14.1 (4)
N4—C7—C10—N3	−0.8 (5)	C1—C6—N4—C7	179.3 (4)
C8—C7—C10—N3	177.6 (4)	C5—C6—N4—C7	−2.0 (6)
N4—C7—C10—N2	177.2 (4)	C1—C6—N4—Co1	−16.6 (6)
C8—C7—C10—N2	−4.4 (7)	C5—C6—N4—Co1	162.1 (3)
N3—C11—C12—C13	−179.6 (4)	N3—Co1—N4—C7	−16.7 (3)
C16—C11—C12—C13	1.6 (6)	N1—Co1—N4—C7	−124.1 (3)
C11—C12—C13—C14	0.0 (7)	O1—Co1—N4—C7	−44.1 (11)
C12—C13—C14—C15	−1.2 (8)	O4—Co1—N4—C7	143.1 (3)
C13—C14—C15—C16	0.7 (7)	O1'—Co1—N4—C7	45.8 (9)
C14—C15—C16—C11	0.9 (7)	O6—Co1—N4—C7	89.9 (3)
C14—C15—C16—N2	179.8 (4)	N3—Co1—N4—C6	178.6 (4)
C12—C11—C16—C15	−2.1 (7)	N1—Co1—N4—C6	71.2 (4)
N3—C11—C16—C15	178.8 (4)	O1—Co1—N4—C6	151.1 (8)
C12—C11—C16—N2	178.7 (4)	O4—Co1—N4—C6	−21.7 (4)
N3—C11—C16—N2	−0.4 (4)	O1'—Co1—N4—C6	−118.9 (9)
N2—C17—C18—C22	−3.8 (7)	O6—Co1—N4—C6	−74.9 (3)
N2—C17—C18—C19	177.6 (5)	O5—N5—O4—Co1	−178.7 (4)
C22—C18—C19—C20	0.4 (8)	O6—N5—O4—Co1	1.5 (4)
C17—C18—C19—C20	179.2 (5)	N3—Co1—O4—N5	20.4 (6)
C18—C19—C20—N1^i	−0.4 (10)	N1—Co1—O4—N5	−160.7 (3)
N1^i—C21—C22—C18	1.1 (9)	O1—Co1—O4—N5	113.8 (3)
C19—C18—C22—C21	−0.8 (8)	O1'—Co1—O4—N5	72.9 (4)
C17—C18—C22—C21	−179.4 (5)	O6—Co1—O4—N5	−0.9 (2)
Cl1—C23—Cl2—Cl2^ii	15.8 (7)	N4—Co1—O4—N5	−67.3 (3)
N3—Co1—N1—C21^iii	134.8 (4)	O5—N5—O6—Co1	178.7 (4)
O1—Co1—N1—C21^iii	39.4 (4)	O4—N5—O6—Co1	−1.5 (4)
O4—Co1—N1—C21^iii	−44.8 (4)	N3—Co1—O6—N5	−171.9 (2)
O1'—Co1—N1—C21^iii	38.8 (8)	N1—Co1—O6—N5	38.2 (4)
O6—Co1—N1—C21^iii	−76.0 (5)	O1—Co1—O6—N5	−70.7 (3)
N4—Co1—N1—C21^iii	−149.2 (4)	O4—Co1—O6—N5	0.9 (2)
N3—Co1—N1—C20^iii	−41.2 (5)	O1'—Co1—O6—N5	−92.0 (5)
O1—Co1—N1—C20^iii	−136.6 (5)	N4—Co1—O6—N5	115.8 (3)
O4—Co1—N1—C20^iii	139.2 (5)	O2—N6—O1—Co1	−172.4 (4)
O1'—Co1—N1—C20^iii	−137.1 (8)	O1'—N6—O1—Co1	−17.3 (11)
O6—Co1—N1—C20^iii	108.1 (5)	O2'—N6—O1—Co1	179 (5)
N4—Co1—N1—C20^iii	34.8 (5)	O3—N6—O1—Co1	6.7 (6)
N3—C10—N2—C16	0.2 (5)	O3'—N6—O1—Co1	161.8 (17)
C7—C10—N2—C16	−177.8 (4)	N3—Co1—O1—N6	87.8 (4)
N3—C10—N2—C17	−179.2 (4)	N1—Co1—O1—N6	−165.0 (4)
C7—C10—N2—C17	2.7 (7)	O4—Co1—O1—N6	−72.5 (4)
C15—C16—N2—C10	−179.0 (5)	O1'—Co1—O1—N6	14.3 (9)
C11—C16—N2—C10	0.1 (4)	O6—Co1—O1—N6	−17.8 (4)
C15—C16—N2—C17	0.5 (7)	N4—Co1—O1—N6	114.5 (9)
C11—C16—N2—C17	179.6 (4)	O2—N6—O1'—Co1	143.1 (12)
C18—C17—N2—C10	−78.4 (6)	O2'—N6—O1'—Co1	−169.5 (19)
C18—C17—N2—C16	102.3 (5)	O1—N6—O1'—Co1	15.7 (9)
N2—C10—N3—C11	−0.5 (5)	O3—N6—O1'—Co1	−136.9 (19)
C7—C10—N3—C11	177.9 (3)	O3'—N6—O1'—Co1	15 (2)
N2—C10—N3—Co1	167.2 (3)	N3—Co1—O1'—N6	−120.6 (15)
C7—C10—N3—Co1	−14.5 (5)	N1—Co1—O1'—N6	−13.0 (18)
C12—C11—N3—C10	−178.5 (4)	O1—Co1—O1'—N6	−13.8 (8)
C16—C11—N3—C10	0.5 (4)	O4—Co1—O1'—N6	74.9 (14)
C12—C11—N3—Co1	17.3 (7)	O6—Co1—O1'—N6	134.2 (16)
C16—C11—N3—Co1	−163.7 (3)	N4—Co1—O1'—N6	179.6 (8)

Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) −x+1, −y+1, −z+1; (iii) −x+1/2, y−1/2, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Cl2′^ii	0.93	2.71	3.556 (8)	152

Symmetry code: (ii) −x+1, −y+1, −z+1.

catena-poly[[[dichloridocobalt(II)]-µ-2-[1-(pyridin-4-ylmethyl)-1H-benzimidazol-2-yl]quinoline] methanol disolvate] (II)

Crystal data

[CoCl2(C22H16N4)]·2CH4O	F(000) = 2184
Mr = 530.30	Dx = 1.462 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P2ac2ab	Cell parameters from 3838 reflections
a = 18.2319 (8) Å	θ = 3.3–28.1°
b = 14.2937 (7) Å	µ = 0.96 mm^−1
c = 18.4926 (8) Å	T = 289 K
V = 4819.2 (4) Å^3	Plate, clear light purple
Z = 8	0.17 × 0.06 × 0.02 mm

Data collection

Agilent SuperNova Dual diffractometer (Cu at zero) with Eos detector	4916 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	3430 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.051
Detector resolution: 16.0793 pixels mm^-1	θmax = 26.4°, θmin = 3.1°
ω scans	h = −22→17
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	k = −17→16
Tmin = 0.724, Tmax = 1.000	l = −14→23
16469 measured reflections

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.130	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.039P)^2 + 7.013P] where P = (Fo^2 + 2Fc^2)/3
4916 reflections	(Δ/σ)max < 0.001
301 parameters	Δρmax = 0.57 e Å^−3
0 restraints	Δρmin = −0.39 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.

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

	x	y	z	Uiso*/Ueq
C1	0.3953 (2)	0.4535 (3)	0.5081 (2)	0.0471 (10)
H1	0.4401	0.4241	0.4998	0.057*
C2	0.3922 (3)	0.5330 (3)	0.5491 (2)	0.0553 (12)
H2	0.4350	0.5566	0.5696	0.066*
C3	0.3258 (3)	0.5791 (3)	0.5606 (2)	0.0605 (13)
H3	0.3251	0.6341	0.5875	0.073*
C4	0.2620 (3)	0.5450 (3)	0.5332 (2)	0.0579 (12)
H4	0.2181	0.5763	0.5417	0.070*
C5	0.2624 (2)	0.4613 (3)	0.4915 (2)	0.0439 (10)
C6	0.3298 (2)	0.4160 (3)	0.47828 (19)	0.0382 (9)
C7	0.2713 (2)	0.2976 (3)	0.41475 (19)	0.0352 (8)
C8	0.2025 (2)	0.3395 (3)	0.4253 (2)	0.0454 (10)
H8	0.1603	0.3123	0.4064	0.054*
C9	0.1985 (2)	0.4209 (3)	0.4637 (2)	0.0510 (11)
H9	0.1533	0.4495	0.4713	0.061*
C10	0.2834 (2)	0.2101 (3)	0.37404 (19)	0.0343 (8)
C11	0.3457 (2)	0.1009 (3)	0.3190 (2)	0.0365 (9)
C12	0.3984 (2)	0.0425 (3)	0.2885 (2)	0.0450 (10)
H12	0.4479	0.0584	0.2894	0.054*
C13	0.3753 (2)	−0.0387 (3)	0.2574 (2)	0.0494 (10)
H13	0.4096	−0.0782	0.2363	0.059*
C14	0.3011 (2)	−0.0643 (3)	0.2565 (2)	0.0506 (11)
H14	0.2875	−0.1202	0.2346	0.061*
C15	0.2482 (2)	−0.0091 (3)	0.2868 (2)	0.0444 (10)
H15	0.1989	−0.0258	0.2863	0.053*
C16	0.2724 (2)	0.0732 (3)	0.31846 (19)	0.0354 (8)
C17	0.15517 (18)	0.1374 (3)	0.37024 (19)	0.0355 (8)
H17A	0.1448	0.1717	0.4143	0.043*
H17B	0.1429	0.0723	0.3788	0.043*
C18	0.10646 (19)	0.1747 (2)	0.31032 (18)	0.0328 (8)
C19	0.1287 (2)	0.1791 (3)	0.2390 (2)	0.0457 (10)
H19	0.1767	0.1638	0.2267	0.055*
C20	0.0799 (2)	0.2060 (3)	0.1859 (2)	0.0416 (10)
H20	0.0958	0.2069	0.1381	0.050*
C21	−0.0091 (2)	0.2293 (3)	0.2697 (2)	0.0463 (10)
H21	−0.0564	0.2487	0.2812	0.056*
C22	0.0357 (2)	0.2011 (3)	0.3254 (2)	0.0443 (10)
H22	0.0183	0.1999	0.3726	0.053*
C23	0.6940 (4)	0.6997 (5)	0.3690 (3)	0.110 (2)
H23A	0.7368	0.7019	0.3992	0.165*
H23B	0.6933	0.6419	0.3426	0.165*
H23C	0.6508	0.7040	0.3985	0.165*
C24	0.5529 (5)	0.9515 (6)	0.3888 (5)	0.154 (4)
H24A	0.5473	0.9973	0.4264	0.230*
H24B	0.5056	0.9277	0.3755	0.230*
H24C	0.5756	0.9799	0.3475	0.230*
Cl1	0.44190 (6)	0.42588 (7)	0.32612 (6)	0.0484 (3)
Cl2	0.50193 (6)	0.23942 (8)	0.47847 (5)	0.0549 (3)
Co1	0.43332 (3)	0.27980 (4)	0.37805 (3)	0.03437 (16)
N1	0.35141 (16)	0.1871 (2)	0.35414 (16)	0.0364 (7)
N2	0.23365 (15)	0.1442 (2)	0.35460 (16)	0.0340 (7)
N3	0.33365 (16)	0.3353 (2)	0.43845 (16)	0.0363 (7)
N4	0.01079 (16)	0.2307 (2)	0.20042 (16)	0.0349 (7)
O1	0.5961 (3)	0.8793 (5)	0.4134 (4)	0.162 (2)
H1A	0.5768	0.8552	0.4489	0.244*
O2	0.6955 (3)	0.7720 (4)	0.3220 (3)	0.1217 (17)
H2A	0.6684	0.8233	0.3425	0.183*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.042 (2)	0.056 (3)	0.043 (2)	−0.007 (2)	0.0000 (19)	−0.006 (2)
C2	0.058 (3)	0.063 (3)	0.045 (2)	−0.017 (2)	−0.003 (2)	−0.016 (2)
C3	0.071 (3)	0.054 (3)	0.057 (3)	−0.008 (3)	0.010 (3)	−0.021 (2)
C4	0.056 (3)	0.061 (3)	0.057 (3)	0.003 (2)	0.016 (2)	−0.016 (2)
C5	0.042 (2)	0.048 (2)	0.041 (2)	−0.004 (2)	0.0073 (19)	−0.0104 (19)
C6	0.039 (2)	0.044 (2)	0.0313 (18)	−0.0025 (19)	0.0019 (17)	−0.0033 (17)
C7	0.032 (2)	0.043 (2)	0.0306 (18)	−0.0011 (17)	0.0019 (16)	−0.0025 (16)
C8	0.032 (2)	0.054 (3)	0.050 (2)	−0.0025 (19)	−0.0026 (19)	−0.013 (2)
C9	0.038 (2)	0.059 (3)	0.055 (3)	0.005 (2)	0.007 (2)	−0.011 (2)
C10	0.0275 (18)	0.043 (2)	0.0327 (18)	−0.0012 (17)	−0.0005 (16)	−0.0025 (16)
C11	0.0294 (19)	0.043 (2)	0.037 (2)	−0.0019 (18)	−0.0008 (17)	−0.0005 (17)
C12	0.033 (2)	0.049 (2)	0.053 (2)	0.0010 (19)	0.0005 (19)	−0.005 (2)
C13	0.046 (2)	0.045 (2)	0.057 (3)	0.007 (2)	0.010 (2)	−0.008 (2)
C14	0.054 (3)	0.041 (2)	0.057 (3)	−0.004 (2)	−0.001 (2)	−0.012 (2)
C15	0.037 (2)	0.045 (2)	0.051 (2)	−0.006 (2)	−0.004 (2)	−0.0049 (19)
C16	0.036 (2)	0.037 (2)	0.0338 (19)	0.0018 (18)	−0.0041 (17)	−0.0010 (16)
C17	0.0250 (18)	0.045 (2)	0.0365 (19)	−0.0022 (17)	0.0022 (16)	0.0024 (17)
C18	0.0287 (19)	0.039 (2)	0.0313 (18)	−0.0042 (17)	−0.0029 (16)	−0.0006 (16)
C19	0.0273 (19)	0.070 (3)	0.039 (2)	0.003 (2)	0.0011 (17)	0.005 (2)
C20	0.035 (2)	0.057 (3)	0.0323 (19)	0.0038 (19)	0.0051 (17)	0.0045 (18)
C21	0.030 (2)	0.069 (3)	0.040 (2)	0.016 (2)	0.0028 (18)	−0.001 (2)
C22	0.037 (2)	0.063 (3)	0.033 (2)	0.005 (2)	0.0058 (17)	−0.0016 (19)
C23	0.117 (6)	0.128 (6)	0.084 (4)	−0.016 (5)	0.011 (4)	0.040 (4)
C24	0.204 (10)	0.106 (6)	0.151 (7)	0.014 (6)	−0.095 (7)	0.039 (5)
Cl1	0.0429 (6)	0.0490 (6)	0.0534 (6)	0.0059 (5)	0.0105 (5)	0.0052 (5)
Cl2	0.0562 (7)	0.0730 (7)	0.0354 (5)	0.0078 (6)	−0.0068 (5)	0.0016 (5)
Co1	0.0274 (3)	0.0429 (3)	0.0328 (3)	−0.0031 (2)	−0.0004 (2)	−0.0026 (2)
N1	0.0289 (16)	0.0437 (18)	0.0365 (16)	−0.0008 (15)	−0.0030 (14)	−0.0062 (14)
N2	0.0258 (16)	0.0403 (17)	0.0358 (16)	0.0000 (14)	−0.0029 (13)	−0.0005 (14)
N3	0.0299 (16)	0.0448 (18)	0.0342 (16)	−0.0055 (15)	0.0025 (14)	−0.0045 (14)
N4	0.0275 (15)	0.0410 (17)	0.0361 (16)	−0.0006 (14)	−0.0002 (14)	0.0033 (14)
O1	0.104 (4)	0.203 (6)	0.180 (6)	−0.033 (4)	−0.010 (4)	0.079 (5)
O2	0.122 (4)	0.132 (4)	0.111 (4)	−0.038 (3)	0.012 (3)	0.038 (3)

Geometric parameters (Å, º)

C1—C2	1.367 (6)	C16—N2	1.405 (4)
C1—C6	1.420 (5)	C17—N2	1.463 (4)
C1—H1	0.9300	C17—C18	1.517 (5)
C2—C3	1.396 (6)	C17—H17A	0.9700
C2—H2	0.9300	C17—H17B	0.9700
C3—C4	1.358 (6)	C18—C22	1.372 (5)
C3—H3	0.9300	C18—C19	1.381 (5)
C4—C5	1.423 (6)	C19—C20	1.380 (5)
C4—H4	0.9300	C19—H19	0.9300
C5—C9	1.398 (6)	C20—N4	1.336 (4)
C5—C6	1.411 (5)	C20—H20	0.9300
C6—N3	1.370 (5)	C21—N4	1.332 (5)
C7—N3	1.333 (4)	C21—C22	1.375 (5)
C7—C8	1.404 (5)	C21—H21	0.9300
C7—C10	1.477 (5)	C22—H22	0.9300
C8—C9	1.365 (6)	C23—O2	1.350 (7)
C8—H8	0.9300	C23—H23A	0.9600
C9—H9	0.9300	C23—H23B	0.9600
C10—N1	1.335 (4)	C23—H23C	0.9600
C10—N2	1.355 (4)	C24—O1	1.376 (8)
C11—C12	1.392 (5)	C24—H24A	0.9600
C11—C16	1.394 (5)	C24—H24B	0.9600
C11—N1	1.397 (5)	C24—H24C	0.9600
C12—C13	1.362 (6)	Co1—Cl1	2.304 (2)
C12—H12	0.9300	Co1—Cl2	2.312 (2)
C13—C14	1.401 (6)	Co1—N1	2.045 (3)
C13—H13	0.9300	Co1—N4^i	2.143 (3)
C14—C15	1.366 (6)	Co1—N3	2.276 (3)
C14—H14	0.9300	N4—Co1^ii	2.143 (3)
C15—C16	1.386 (5)	O1—H1A	0.8200
C15—H15	0.9300	O2—H2A	0.9602
C2—C1—C6	119.6 (4)	H17A—C17—H17B	107.7
C2—C1—H1	120.2	C22—C18—C19	117.2 (3)
C6—C1—H1	120.2	C22—C18—C17	119.9 (3)
C1—C2—C3	120.9 (4)	C19—C18—C17	122.8 (3)
C1—C2—H2	119.5	C20—C19—C18	120.1 (3)
C3—C2—H2	119.5	C20—C19—H19	119.9
C4—C3—C2	121.1 (4)	C18—C19—H19	119.9
C4—C3—H3	119.5	N4—C20—C19	122.6 (3)
C2—C3—H3	119.5	N4—C20—H20	118.7
C3—C4—C5	120.0 (4)	C19—C20—H20	118.7
C3—C4—H4	120.0	N4—C21—C22	124.2 (3)
C5—C4—H4	120.0	N4—C21—H21	117.9
C9—C5—C6	118.2 (4)	C22—C21—H21	117.9
C9—C5—C4	122.8 (4)	C18—C22—C21	119.2 (3)
C6—C5—C4	119.0 (4)	C18—C22—H22	120.4
N3—C6—C5	121.6 (3)	C21—C22—H22	120.4
N3—C6—C1	118.9 (3)	O2—C23—H23A	109.5
C5—C6—C1	119.5 (3)	O2—C23—H23B	109.5
N3—C7—C8	122.9 (3)	H23A—C23—H23B	109.5
N3—C7—C10	112.5 (3)	O2—C23—H23C	109.5
C8—C7—C10	124.5 (3)	H23A—C23—H23C	109.5
C9—C8—C7	118.9 (4)	H23B—C23—H23C	109.5
C9—C8—H8	120.5	O1—C24—H24A	109.5
C7—C8—H8	120.5	O1—C24—H24B	109.5
C8—C9—C5	120.0 (4)	H24A—C24—H24B	109.5
C8—C9—H9	120.0	O1—C24—H24C	109.5
C5—C9—H9	120.0	H24A—C24—H24C	109.5
N1—C10—N2	112.2 (3)	H24B—C24—H24C	109.5
N1—C10—C7	119.2 (3)	N1—Co1—N4^i	97.07 (12)
N2—C10—C7	128.6 (3)	N1—Co1—N3	75.45 (11)
C12—C11—C16	119.3 (3)	N4^i—Co1—N3	166.57 (11)
C12—C11—N1	131.8 (3)	N1—Co1—Cl1	123.14 (9)
C16—C11—N1	108.9 (3)	N4^i—Co1—Cl1	88.25 (9)
C13—C12—C11	117.9 (4)	N3—Co1—Cl1	86.72 (8)
C13—C12—H12	121.1	N1—Co1—Cl2	114.03 (9)
C11—C12—H12	121.1	N4^i—Co1—Cl2	96.07 (9)
C12—C13—C14	121.8 (4)	N3—Co1—Cl2	97.17 (8)
C12—C13—H13	119.1	Cl1—Co1—Cl2	121.62 (5)
C14—C13—H13	119.1	C10—N1—C11	106.0 (3)
C15—C14—C13	121.7 (4)	C10—N1—Co1	117.4 (2)
C15—C14—H14	119.1	C11—N1—Co1	136.6 (2)
C13—C14—H14	119.1	C10—N2—C16	106.9 (3)
C14—C15—C16	116.1 (4)	C10—N2—C17	130.4 (3)
C14—C15—H15	122.0	C16—N2—C17	122.5 (3)
C16—C15—H15	122.0	C7—N3—C6	118.3 (3)
C15—C16—C11	123.2 (4)	C7—N3—Co1	112.3 (2)
C15—C16—N2	130.8 (3)	C6—N3—Co1	126.7 (2)
C11—C16—N2	105.9 (3)	C21—N4—C20	116.5 (3)
N2—C17—C18	113.9 (3)	C21—N4—Co1^ii	118.5 (2)
N2—C17—H17A	108.8	C20—N4—Co1^ii	124.9 (3)
C18—C17—H17A	108.8	C24—O1—H1A	109.5
N2—C17—H17B	108.8	C23—O2—H2A	108.7
C18—C17—H17B	108.8
C6—C1—C2—C3	−1.5 (7)	C12—C11—N1—C10	−178.3 (4)
C1—C2—C3—C4	1.9 (7)	C16—C11—N1—C10	0.1 (4)
C2—C3—C4—C5	−0.5 (7)	C12—C11—N1—Co1	3.2 (7)
C3—C4—C5—C9	177.9 (4)	C16—C11—N1—Co1	−178.4 (3)
C3—C4—C5—C6	−1.2 (7)	N4^i—Co1—N1—C10	−159.1 (3)
C9—C5—C6—N3	0.9 (6)	N3—Co1—N1—C10	9.6 (3)
C4—C5—C6—N3	−179.9 (4)	Cl1—Co1—N1—C10	−66.5 (3)
C9—C5—C6—C1	−177.7 (4)	Cl2—Co1—N1—C10	101.0 (3)
C4—C5—C6—C1	1.5 (6)	N4^i—Co1—N1—C11	19.3 (4)
C2—C1—C6—N3	−178.8 (4)	N3—Co1—N1—C11	−172.1 (4)
C2—C1—C6—C5	−0.1 (6)	Cl1—Co1—N1—C11	111.8 (3)
N3—C7—C8—C9	−2.4 (6)	Cl2—Co1—N1—C11	−80.6 (4)
C10—C7—C8—C9	−179.6 (4)	N1—C10—N2—C16	−0.7 (4)
C7—C8—C9—C5	0.3 (6)	C7—C10—N2—C16	−178.4 (3)
C6—C5—C9—C8	0.4 (6)	N1—C10—N2—C17	174.7 (3)
C4—C5—C9—C8	−178.7 (4)	C7—C10—N2—C17	−3.0 (6)
N3—C7—C10—N1	−11.7 (5)	C15—C16—N2—C10	−179.0 (4)
C8—C7—C10—N1	165.7 (4)	C11—C16—N2—C10	0.7 (4)
N3—C7—C10—N2	165.8 (3)	C15—C16—N2—C17	5.1 (6)
C8—C7—C10—N2	−16.7 (6)	C11—C16—N2—C17	−175.1 (3)
C16—C11—C12—C13	1.8 (6)	C18—C17—N2—C10	96.5 (4)
N1—C11—C12—C13	−179.9 (4)	C18—C17—N2—C16	−88.8 (4)
C11—C12—C13—C14	−0.8 (6)	C8—C7—N3—C6	3.7 (5)
C12—C13—C14—C15	−0.1 (7)	C10—C7—N3—C6	−178.8 (3)
C13—C14—C15—C16	0.0 (6)	C8—C7—N3—Co1	−158.9 (3)
C14—C15—C16—C11	1.1 (6)	C10—C7—N3—Co1	18.6 (4)
C14—C15—C16—N2	−179.1 (4)	C5—C6—N3—C7	−2.9 (5)
C12—C11—C16—C15	−2.1 (6)	C1—C6—N3—C7	175.7 (3)
N1—C11—C16—C15	179.3 (3)	C5—C6—N3—Co1	156.8 (3)
C12—C11—C16—N2	178.2 (3)	C1—C6—N3—Co1	−24.5 (5)
N1—C11—C16—N2	−0.5 (4)	N1—Co1—N3—C7	−15.9 (2)
N2—C17—C18—C22	−158.8 (3)	N4^i—Co1—N3—C7	41.4 (6)
N2—C17—C18—C19	24.8 (5)	Cl1—Co1—N3—C7	109.6 (2)
C22—C18—C19—C20	−2.2 (6)	Cl2—Co1—N3—C7	−129.0 (2)
C17—C18—C19—C20	174.3 (4)	N1—Co1—N3—C6	−176.7 (3)
C18—C19—C20—N4	1.6 (6)	N4^i—Co1—N3—C6	−119.4 (5)
C19—C18—C22—C21	0.6 (6)	Cl1—Co1—N3—C6	−51.2 (3)
C17—C18—C22—C21	−176.0 (4)	Cl2—Co1—N3—C6	70.2 (3)
N4—C21—C22—C18	1.8 (7)	C22—C21—N4—C20	−2.5 (6)
N2—C10—N1—C11	0.4 (4)	C22—C21—N4—Co1^ii	−178.8 (3)
C7—C10—N1—C11	178.3 (3)	C19—C20—N4—C21	0.7 (6)
N2—C10—N1—Co1	179.2 (2)	C19—C20—N4—Co1^ii	176.8 (3)
C7—C10—N1—Co1	−2.9 (4)

Symmetry codes: (i) x+1/2, y, −z+1/2; (ii) x−1/2, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

Cg1 represents the centroid of the C1–C6 quinoline ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···Cl2^iii	0.82	2.39	3.173 (5)	161
O2—H2A···O1	0.96	2.03	2.914 (9)	153
C15—H15···Cl1^iv	0.93	2.76	3.662 (4)	164
C22—H22···Cl2^v	0.93	2.90	3.777 (4)	157
C17—H17B···Cg1^iv	0.97	2.87	3.429 (2)	117

Symmetry codes: (iii) −x+1, −y+1, −z+1; (iv) −x+1/2, y−1/2, z; (v) x−1/2, −y+1/2, −z+1.