catena-Poly[[[diaqua-cobalt(II)]bis-(μ-1,3-di-4-pyridylpropane-κN:N')] bis-(perchlorate) bis-(1,3-di-4-pyridyl-propane) bis-(2-methyl-4-nitro-aniline)].

In the title compound, {[Co(C(13)H(14)N(2))(2)(H(2)O)(2)](ClO(4))(2)·2C(13)H(14)N(2)·2C(7)H(8)N(2)O(2)}(n), the Co(II) ion lies on a crystallographic inversion center and is coordinated by four N atoms from four symmetry-related 1,3-di-4-pyridylpropane ligands and two O atoms from two water ligands in a slightly distorted octa-hedral coordination environment. The 1,3-di-4-pyridylpropane ligands are doubly bridging and connect the Co(II) ions into one-dimensional chains. The asymmetric unit also contains one uncoordinated 1,3-di-4-pyridylpropane mol-ecule, one 2-methyl-4-nitro-aniline mol-ecule and one perchlorate anion. In the crystal structure, inter-molecular O-H⋯N hydrogen bonds connect the one-dimensional chains into a two-dimensional network.

Related literature

For a related complex with a similar crystal structure, see: Merz et al. (2004 ▶). For related literature, see: James (2003 ▶).

Experimental

Crystal data

[Co(C13H14N2)2(H2O)2](ClO4)2·2C13H14N2·2C7H8N2O2

M = 1391.22

Triclinic,

a = 10.9310 (3) Å

b = 11.6505 (5) Å

c = 15.2054 (4) Å

α = 71.0112 (7)°

β = 82.4011 (6)°

γ = 68.3933 (7)°

V = 1702.22 (10) Å3

Z = 1

Mo Kα radiation

μ = 0.40 mm−1

T = 298 (2) K

0.30 × 0.22 × 0.1 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.892, T max = 0.967

8612 measured reflections

5827 independent reflections

3438 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.168

S = 1.02

5827 reflections

438 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.53 e Å−3

Δρmin = −0.31 e Å−3

Data collection: SMART (Bruker, 1996 ▶); cell refinement: SAINT (Bruker, 1996 ▶); data reduction: SAINT; 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808026470/lh2679sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808026470/lh2679Isup2.hkl

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

[Co(C13H14N2)2(H2O)2](ClO4)2·2C13H14N2·2C7H8N2O2	Z = 1
Mr = 1391.22	F000 = 729
Triclinic, P1	Dx = 1.357 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 10.9310 (3) Å	Cell parameters from 5827 reflections
b = 11.6505 (5) Å	θ = 2.8–25.0º
c = 15.2054 (4) Å	µ = 0.40 mm−1
α = 71.0112 (7)º	T = 298 (2) K
β = 82.4011 (6)º	Block, orange
γ = 68.3933 (7)º	0.30 × 0.22 × 0.1 mm
V = 1702.22 (10) Å3

Bruker SMART CCD diffractometer	5827 independent reflections
Radiation source: fine-focus sealed tube	3438 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.039
T = 298(2) K	θmax = 25.0º
ω scans	θmin = 2.8º
Absorption correction: Multi-scan(SADABS; Sheldrick, 1996)	h = −11→13
Tmin = 0.892, Tmax = 0.967	k = −13→13
8612 measured reflections	l = −18→18

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)] = 0.066	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.168	w = 1/[σ2(Fo2) + (0.0705P)2] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
5827 reflections	Δρmax = 0.53 e Å−3
438 parameters	Δρmin = −0.31 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.0000	0.0000	0.0000	0.0368 (2)
O1	−0.0308 (3)	−0.0246 (3)	0.1425 (2)	0.0450 (8)
H2	−0.095 (4)	0.007 (4)	0.161 (3)	0.035 (14)*
H1	−0.009 (5)	−0.091 (6)	0.190 (4)	0.10 (2)*
O2	0.0102 (8)	−0.3950 (9)	−0.2105 (4)	0.185 (3)
O3	−0.1176 (7)	−0.1911 (10)	−0.2256 (7)	0.218 (5)
O4	0.6660 (4)	−0.3125 (5)	−0.7027 (3)	0.1267 (17)
O5	0.5089 (6)	−0.3630 (6)	−0.7540 (3)	0.146 (2)
O6	0.4479 (6)	−0.1872 (5)	−0.7051 (4)	0.160 (2)
O7	0.5165 (4)	−0.3851 (5)	−0.5995 (3)	0.1177 (16)
N1	−0.1793 (3)	−0.0409 (3)	−0.0082 (2)	0.0380 (8)
N2	−0.1087 (3)	−0.7946 (3)	−0.0213 (2)	0.0412 (8)
N3	−0.0498 (4)	−0.7448 (4)	−0.2812 (3)	0.0679 (11)
N4	−0.7219 (4)	−0.0999 (4)	−0.2125 (3)	0.0621 (10)
N5	0.3025 (6)	−0.1123 (7)	−0.5321 (4)	0.139 (2)
H5A	0.3638	−0.1666	−0.5550	0.167*
H5B	0.2891	−0.0309	−0.5548	0.167*
N6	−0.0249 (11)	−0.2734 (10)	−0.2435 (5)	0.156 (4)
C1	−0.2391 (4)	−0.0147 (3)	−0.0875 (3)	0.0422 (10)
H1A	−0.2139	0.0379	−0.1416	0.051*
C2	−0.3361 (4)	−0.0616 (4)	−0.0933 (3)	0.0464 (10)
H2A	−0.3749	−0.0399	−0.1501	0.056*
C3	−0.2207 (4)	−0.1150 (4)	0.0678 (3)	0.0499 (11)
H3A	−0.1830	−0.1329	0.1243	0.060*
C4	−0.3148 (4)	−0.1659 (4)	0.0676 (3)	0.0507 (11)
H4A	−0.3386	−0.2177	0.1229	0.061*
C5	−0.3749 (4)	−0.1408 (4)	−0.0143 (3)	0.0455 (11)
C6	−0.4719 (4)	−0.2046 (4)	−0.0158 (3)	0.0528 (11)
H6A	−0.5153	−0.1653	−0.0754	0.063*
H6B	−0.5386	−0.1897	0.0321	0.063*
C7	−0.4055 (4)	−0.3506 (4)	0.0001 (3)	0.0521 (11)
H7A	−0.3683	−0.3907	0.0619	0.062*
H7B	−0.4714	−0.3867	−0.0025	0.062*
C8	−0.2983 (4)	−0.3827 (4)	−0.0706 (3)	0.0528 (11)
H8A	−0.3356	−0.3428	−0.1323	0.063*
H8B	−0.2325	−0.3462	−0.0680	0.063*
C9	−0.2331 (4)	−0.5255 (4)	−0.0547 (3)	0.0426 (10)
C10	−0.1315 (4)	−0.5980 (4)	0.0076 (3)	0.0513 (11)
H10A	−0.1023	−0.5576	0.0398	0.062*
C11	−0.0732 (4)	−0.7292 (4)	0.0225 (3)	0.0488 (11)
H11A	−0.0055	−0.7749	0.0652	0.059*
C12	−0.2711 (4)	−0.5940 (4)	−0.0986 (3)	0.0484 (10)
H12A	−0.3400	−0.5508	−0.1405	0.058*
C13	−0.2081 (4)	−0.7249 (4)	−0.0807 (3)	0.0450 (10)
H13A	−0.2360	−0.7676	−0.1117	0.054*
C14	−0.1616 (6)	−0.7095 (5)	−0.3234 (4)	0.0786 (15)
H14A	−0.2033	−0.7700	−0.3105	0.094*
C15	−0.2205 (5)	−0.5909 (5)	−0.3846 (4)	0.0716 (14)
H15A	−0.2992	−0.5733	−0.4120	0.086*
C16	0.0060 (5)	−0.6559 (5)	−0.3035 (4)	0.0723 (14)
H16A	0.0856	−0.6768	−0.2760	0.087*
C17	−0.0468 (5)	−0.5330 (5)	−0.3655 (4)	0.0681 (14)
H17A	−0.0019	−0.4751	−0.3792	0.082*
C18	−0.1640 (4)	−0.4972 (4)	−0.4060 (3)	0.0536 (11)
C19	−0.2286 (5)	−0.3641 (5)	−0.4704 (3)	0.0738 (14)
H19A	−0.2426	−0.3711	−0.5298	0.089*
H19B	−0.1699	−0.3154	−0.4809	0.089*
C20	−0.3608 (6)	−0.2899 (5)	−0.4324 (4)	0.0908 (18)
H20A	−0.3999	−0.2071	−0.4786	0.109*
H20B	−0.4196	−0.3383	−0.4226	0.109*
C21	−0.3491 (5)	−0.2670 (5)	−0.3435 (4)	0.0829 (16)
H21A	−0.2998	−0.2092	−0.3551	0.099*
H21B	−0.3000	−0.3485	−0.2997	0.099*
C22	−0.4832 (5)	−0.2082 (5)	−0.2996 (3)	0.0655 (13)
C23	−0.5308 (5)	−0.0799 (5)	−0.3042 (3)	0.0755 (15)
H23A	−0.4834	−0.0265	−0.3359	0.091*
C24	−0.6487 (5)	−0.0307 (5)	−0.2618 (3)	0.0696 (14)
H24A	−0.6797	0.0573	−0.2677	0.084*
C25	−0.5612 (5)	−0.2796 (5)	−0.2533 (4)	0.0686 (14)
H25A	−0.5359	−0.3659	−0.2511	0.082*
C26	−0.6763 (5)	−0.2240 (5)	−0.2102 (3)	0.0642 (13)
H26A	−0.7251	−0.2757	−0.1776	0.077*
C27	0.1226 (7)	0.0718 (7)	−0.4533 (5)	0.120 (2)
H27A	0.0538	0.1196	−0.4192	0.180*
H27B	0.1029	0.1068	−0.5184	0.180*
H27C	0.2046	0.0781	−0.4435	0.180*
C28	0.1332 (6)	−0.0690 (6)	−0.4197 (4)	0.0822 (16)
C29	0.2250 (6)	−0.1562 (7)	−0.4586 (4)	0.0839 (17)
C30	0.2475 (6)	−0.2857 (7)	−0.4235 (5)	0.0873 (17)
H30A	0.3157	−0.3425	−0.4485	0.105*
C31	0.1723 (7)	−0.3344 (6)	−0.3523 (5)	0.0910 (18)
H31A	0.1872	−0.4226	−0.3277	0.109*
C32	0.0689 (6)	−0.2398 (8)	−0.3182 (4)	0.086 (2)
C33	0.0569 (6)	−0.1127 (7)	−0.3516 (4)	0.0845 (17)
H33A	−0.0073	−0.0540	−0.3257	0.101*
Cl1	0.53712 (14)	−0.31378 (14)	−0.69036 (9)	0.0756 (4)

	U11	U22	U33	U12	U13	U23
Co1	0.0321 (4)	0.0319 (4)	0.0486 (5)	−0.0089 (3)	0.0030 (4)	−0.0188 (4)
O1	0.0393 (19)	0.0465 (19)	0.0476 (19)	−0.0105 (15)	0.0078 (16)	−0.0203 (17)
O2	0.257 (8)	0.263 (9)	0.105 (4)	−0.181 (8)	0.027 (5)	−0.054 (5)
O3	0.150 (6)	0.336 (12)	0.284 (9)	−0.104 (6)	0.096 (6)	−0.257 (9)
O4	0.084 (3)	0.198 (5)	0.098 (3)	−0.081 (3)	0.011 (3)	−0.014 (3)
O5	0.168 (5)	0.224 (6)	0.110 (4)	−0.110 (5)	0.030 (3)	−0.097 (4)
O6	0.159 (5)	0.099 (4)	0.183 (5)	−0.025 (3)	0.006 (4)	−0.017 (4)
O7	0.121 (3)	0.154 (4)	0.077 (3)	−0.079 (3)	0.013 (3)	−0.001 (3)
N1	0.0388 (19)	0.0339 (18)	0.0442 (19)	−0.0108 (14)	0.0062 (16)	−0.0202 (15)
N2	0.0374 (19)	0.0380 (19)	0.0479 (19)	−0.0095 (15)	0.0041 (16)	−0.0185 (16)
N3	0.057 (3)	0.063 (3)	0.067 (3)	−0.008 (2)	0.009 (2)	−0.016 (2)
N4	0.041 (2)	0.073 (3)	0.068 (3)	−0.005 (2)	−0.001 (2)	−0.033 (2)
N5	0.126 (5)	0.208 (7)	0.109 (4)	−0.096 (5)	0.034 (4)	−0.051 (4)
N6	0.242 (10)	0.174 (8)	0.120 (6)	−0.154 (9)	−0.045 (7)	−0.020 (6)
C1	0.043 (2)	0.034 (2)	0.051 (3)	−0.0155 (18)	0.001 (2)	−0.0131 (19)
C2	0.043 (2)	0.034 (2)	0.065 (3)	−0.0071 (19)	−0.007 (2)	−0.023 (2)
C3	0.054 (3)	0.055 (3)	0.049 (3)	−0.026 (2)	0.002 (2)	−0.019 (2)
C4	0.049 (3)	0.059 (3)	0.057 (3)	−0.032 (2)	0.011 (2)	−0.024 (2)
C5	0.028 (2)	0.032 (2)	0.081 (3)	−0.0046 (17)	0.004 (2)	−0.030 (2)
C6	0.029 (2)	0.049 (3)	0.088 (3)	−0.0095 (19)	0.005 (2)	−0.037 (2)
C7	0.043 (2)	0.037 (2)	0.084 (3)	−0.0168 (19)	0.009 (2)	−0.029 (2)
C8	0.062 (3)	0.032 (2)	0.062 (3)	−0.013 (2)	0.011 (2)	−0.019 (2)
C9	0.039 (2)	0.033 (2)	0.053 (2)	−0.0119 (18)	0.012 (2)	−0.0160 (19)
C10	0.049 (3)	0.044 (3)	0.068 (3)	−0.014 (2)	0.003 (2)	−0.031 (2)
C11	0.046 (3)	0.041 (2)	0.060 (3)	−0.0072 (19)	−0.009 (2)	−0.023 (2)
C12	0.044 (2)	0.036 (2)	0.062 (3)	−0.0081 (19)	−0.004 (2)	−0.015 (2)
C13	0.043 (2)	0.041 (2)	0.058 (3)	−0.0158 (19)	0.004 (2)	−0.024 (2)
C14	0.074 (4)	0.072 (4)	0.095 (4)	−0.030 (3)	0.005 (3)	−0.028 (3)
C15	0.058 (3)	0.081 (4)	0.077 (4)	−0.015 (3)	−0.010 (3)	−0.030 (3)
C16	0.047 (3)	0.084 (4)	0.078 (4)	−0.018 (3)	−0.005 (3)	−0.017 (3)
C17	0.055 (3)	0.066 (3)	0.082 (4)	−0.025 (3)	0.004 (3)	−0.018 (3)
C18	0.044 (3)	0.058 (3)	0.050 (3)	−0.003 (2)	0.008 (2)	−0.025 (2)
C19	0.066 (3)	0.072 (3)	0.058 (3)	−0.002 (3)	0.011 (3)	−0.018 (3)
C20	0.090 (4)	0.081 (4)	0.061 (3)	0.015 (3)	−0.004 (3)	−0.019 (3)
C21	0.066 (4)	0.084 (4)	0.085 (4)	−0.003 (3)	−0.004 (3)	−0.033 (3)
C22	0.052 (3)	0.075 (4)	0.061 (3)	−0.006 (3)	0.005 (2)	−0.029 (3)
C23	0.074 (4)	0.073 (4)	0.069 (3)	−0.018 (3)	0.017 (3)	−0.024 (3)
C24	0.067 (3)	0.063 (3)	0.070 (3)	−0.005 (3)	0.009 (3)	−0.032 (3)
C25	0.057 (3)	0.060 (3)	0.083 (4)	−0.001 (3)	−0.007 (3)	−0.035 (3)
C26	0.051 (3)	0.075 (4)	0.065 (3)	−0.017 (3)	−0.005 (3)	−0.023 (3)
C27	0.131 (6)	0.113 (6)	0.127 (6)	−0.042 (5)	−0.030 (5)	−0.038 (5)
C28	0.073 (4)	0.100 (5)	0.078 (4)	−0.024 (4)	−0.012 (4)	−0.036 (4)
C29	0.073 (4)	0.120 (6)	0.078 (4)	−0.045 (4)	0.000 (3)	−0.041 (4)
C30	0.074 (4)	0.104 (5)	0.096 (5)	−0.027 (4)	0.004 (4)	−0.052 (4)
C31	0.099 (5)	0.094 (5)	0.101 (5)	−0.041 (4)	−0.019 (4)	−0.040 (4)
C32	0.089 (5)	0.156 (7)	0.051 (3)	−0.083 (5)	0.005 (3)	−0.034 (4)
C33	0.065 (4)	0.119 (5)	0.091 (4)	−0.032 (4)	0.003 (3)	−0.061 (4)
Cl1	0.0767 (10)	0.0836 (10)	0.0635 (8)	−0.0338 (8)	0.0127 (7)	−0.0164 (7)

Co1—O1i	2.090 (3)	C9—C12	1.385 (5)
Co1—O1	2.090 (3)	C10—C11	1.374 (5)
Co1—N2ii	2.179 (3)	C10—H10A	0.9300
Co1—N2iii	2.179 (3)	C11—H11A	0.9300
Co1—N1	2.208 (3)	C12—C13	1.371 (5)
Co1—N1i	2.208 (3)	C12—H12A	0.9300
O1—H2	0.73 (4)	C13—H13A	0.9300
O1—H1	0.85 (6)	C14—C15	1.362 (7)
O2—N6	1.263 (10)	C14—H14A	0.9300
O3—N6	1.183 (12)	C15—C18	1.375 (6)
O4—Cl1	1.402 (4)	C15—H15A	0.9300
O5—Cl1	1.390 (4)	C16—C17	1.389 (6)
O6—Cl1	1.400 (5)	C16—H16A	0.9300
O7—Cl1	1.400 (4)	C17—C18	1.358 (6)
N1—C3	1.336 (5)	C17—H17A	0.9300
N1—C1	1.340 (4)	C18—C19	1.500 (6)
N2—C11	1.337 (5)	C19—C20	1.534 (7)
N2—C13	1.338 (5)	C19—H19A	0.9700
N2—Co1iv	2.179 (3)	C19—H19B	0.9700
N3—C14	1.319 (6)	C20—C21	1.490 (7)
N3—C16	1.320 (6)	C20—H20A	0.9700
N4—C24	1.333 (6)	C20—H20B	0.9700
N4—C26	1.334 (6)	C21—C22	1.537 (7)
N5—C29	1.387 (7)	C21—H21A	0.9700
N5—H5A	0.8600	C21—H21B	0.9700
N5—H5B	0.8600	C22—C23	1.371 (7)
N6—C32	1.481 (10)	C22—C25	1.377 (7)
C1—C2	1.383 (5)	C23—C24	1.372 (7)
C1—H1A	0.9300	C23—H23A	0.9300
C2—C5	1.382 (5)	C24—H24A	0.9300
C2—H2A	0.9300	C25—C26	1.375 (6)
C3—C4	1.365 (5)	C25—H25A	0.9300
C3—H3A	0.9300	C26—H26A	0.9300
C4—C5	1.381 (6)	C27—C28	1.516 (8)
C4—H4A	0.9300	C27—H27A	0.9600
C5—C6	1.508 (5)	C27—H27B	0.9600
C6—C7	1.531 (5)	C27—H27C	0.9600
C6—H6A	0.9700	C28—C33	1.329 (8)
C6—H6B	0.9700	C28—C29	1.368 (8)
C7—C8	1.508 (6)	C29—C30	1.363 (8)
C7—H7A	0.9700	C30—C31	1.370 (8)
C7—H7B	0.9700	C30—H30A	0.9300
C8—C9	1.498 (5)	C31—C32	1.436 (8)
C8—H8A	0.9700	C31—H31A	0.9300
C8—H8B	0.9700	C32—C33	1.361 (8)
C9—C10	1.383 (5)	C33—H33A	0.9300
O1i—Co1—O1	180	C12—C13—H13A	118.2
O1i—Co1—N2ii	87.06 (13)	N3—C14—C15	124.7 (5)
O1—Co1—N2ii	92.94 (13)	N3—C14—H14A	117.6
O1i—Co1—N2iii	92.94 (13)	C15—C14—H14A	117.6
O1—Co1—N2iii	87.06 (13)	C14—C15—C18	120.3 (5)
N2ii—Co1—N2iii	180	C14—C15—H15A	119.8
O1i—Co1—N1	88.90 (12)	C18—C15—H15A	119.8
O1—Co1—N1	91.10 (12)	N3—C16—C17	124.1 (5)
N2ii—Co1—N1	87.20 (11)	N3—C16—H16A	118.0
N2iii—Co1—N1	92.80 (11)	C17—C16—H16A	118.0
O1i—Co1—N1i	91.10 (12)	C18—C17—C16	120.0 (5)
O1—Co1—N1i	88.90 (12)	C18—C17—H17A	120.0
N2ii—Co1—N1i	92.80 (11)	C16—C17—H17A	120.0
N2iii—Co1—N1i	87.20 (11)	C17—C18—C15	115.8 (4)
N1—Co1—N1i	180	C17—C18—C19	122.4 (5)
Co1—O1—H2	121 (3)	C15—C18—C19	121.7 (4)
Co1—O1—H1	132 (4)	C18—C19—C20	112.9 (4)
H2—O1—H1	95 (5)	C18—C19—H19A	109.0
C3—N1—C1	115.8 (3)	C20—C19—H19A	109.0
C3—N1—Co1	118.7 (3)	C18—C19—H19B	109.0
C1—N1—Co1	124.6 (3)	C20—C19—H19B	109.0
C11—N2—C13	116.0 (3)	H19A—C19—H19B	107.8
C11—N2—Co1iv	120.4 (3)	C21—C20—C19	113.4 (4)
C13—N2—Co1iv	123.6 (2)	C21—C20—H20A	108.9
C14—N3—C16	115.0 (4)	C19—C20—H20A	108.9
C24—N4—C26	115.2 (4)	C21—C20—H20B	108.9
C29—N5—H5A	120.0	C19—C20—H20B	108.9
C29—N5—H5B	120.0	H20A—C20—H20B	107.7
H5A—N5—H5B	120.0	C20—C21—C22	113.0 (4)
O3—N6—O2	130.4 (11)	C20—C21—H21A	109.0
O3—N6—C32	120.4 (10)	C22—C21—H21A	109.0
O2—N6—C32	109.2 (10)	C20—C21—H21B	109.0
N1—C1—C2	123.7 (4)	C22—C21—H21B	109.0
N1—C1—H1A	118.2	H21A—C21—H21B	107.8
C2—C1—H1A	118.2	C23—C22—C25	116.3 (5)
C5—C2—C1	119.6 (4)	C23—C22—C21	120.8 (5)
C5—C2—H2A	120.2	C25—C22—C21	122.9 (5)
C1—C2—H2A	120.2	C24—C23—C22	119.7 (5)
N1—C3—C4	124.0 (4)	C24—C23—H23A	120.1
N1—C3—H3A	118.0	C22—C23—H23A	120.1
C4—C3—H3A	118.0	N4—C24—C23	124.7 (5)
C3—C4—C5	120.2 (4)	N4—C24—H24A	117.7
C3—C4—H4A	119.9	C23—C24—H24A	117.7
C5—C4—H4A	119.9	C26—C25—C22	120.4 (5)
C4—C5—C2	116.7 (3)	C26—C25—H25A	119.8
C4—C5—C6	120.3 (4)	C22—C25—H25A	119.8
C2—C5—C6	123.0 (4)	N4—C26—C25	123.6 (5)
C5—C6—C7	112.2 (3)	N4—C26—H26A	118.2
C5—C6—H6A	109.2	C25—C26—H26A	118.2
C7—C6—H6A	109.2	C28—C27—H27A	109.5
C5—C6—H6B	109.2	C28—C27—H27B	109.5
C7—C6—H6B	109.2	H27A—C27—H27B	109.5
H6A—C6—H6B	107.9	C28—C27—H27C	109.5
C8—C7—C6	112.7 (3)	H27A—C27—H27C	109.5
C8—C7—H7A	109.1	H27B—C27—H27C	109.5
C6—C7—H7A	109.1	C33—C28—C29	117.9 (6)
C8—C7—H7B	109.1	C33—C28—C27	122.1 (7)
C6—C7—H7B	109.1	C29—C28—C27	120.0 (7)
H7A—C7—H7B	107.8	C30—C29—C28	121.7 (6)
C9—C8—C7	112.7 (3)	C30—C29—N5	119.2 (7)
C9—C8—H8A	109.1	C28—C29—N5	119.0 (7)
C7—C8—H8A	109.1	C29—C30—C31	121.8 (6)
C9—C8—H8B	109.1	C29—C30—H30A	119.1
C7—C8—H8B	109.1	C31—C30—H30A	119.1
H8A—C8—H8B	107.8	C30—C31—C32	115.3 (6)
C10—C9—C12	115.6 (3)	C30—C31—H31A	122.3
C10—C9—C8	121.1 (4)	C32—C31—H31A	122.3
C12—C9—C8	123.3 (4)	C33—C32—C31	120.2 (5)
C11—C10—C9	120.7 (4)	C33—C32—N6	116.6 (8)
C11—C10—H10A	119.7	C31—C32—N6	123.2 (8)
C9—C10—H10A	119.7	C28—C33—C32	122.8 (6)
N2—C11—C10	123.5 (4)	C28—C33—H33A	118.6
N2—C11—H11A	118.3	C32—C33—H33A	118.6
C10—C11—H11A	118.3	O5—Cl1—O6	107.3 (4)
C13—C12—C9	120.6 (4)	O5—Cl1—O7	110.2 (3)
C13—C12—H12A	119.7	O6—Cl1—O7	107.4 (3)
C9—C12—H12A	119.7	O5—Cl1—O4	111.1 (3)
N2—C13—C12	123.6 (4)	O6—Cl1—O4	109.6 (3)
N2—C13—H13A	118.2	O7—Cl1—O4	111.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N3ii	0.85 (6)	1.94 (3)	2.744 (5)	173 (4)
O1—H2···N4v	0.73 (4)	2.07 (2)	2.810 (3)	174 (3)

Co1—O1	2.090 (3)
Co1—N2i	2.179 (3)
Co1—N1	2.208 (3)

O1ii—Co1—O1	180
O1ii—Co1—N2i	92.94 (13)
O1—Co1—N2i	87.06 (13)
N2iii—Co1—N2i	180
O1ii—Co1—N1	88.90 (12)
O1—Co1—N1	91.10 (12)
N2iii—Co1—N1	87.20 (11)
N2iii—Co1—N1ii	92.80 (11)
N1—Co1—N1ii	180

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

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N3iii	0.85 (6)	1.94 (3)	2.744 (5)	173 (4)
O1—H2⋯N4iv	0.73 (4)	2.07 (2)	2.810 (3)	174 (3)

Symmetry codes: (iii) ; (iv) .