Bis[1,3-bis-(benzimidazol-2-yl)-2-oxa-propane]cobalt(II) dipicrate acetonitrile tris-olvate.

In the title compound, [Co(C(16)H(14)N(4)O)(2)](C(6)H(2)N(3)O(7))(2)·3CH(3)CN, the Co(II) ion is located on a crystallographic twofold rotation axis and is coordinated in a slightly distorted tetra-hedral environment by four N atoms from the two bidentate N-heterocycles. The crystal structure is stabilized by inter-molecular N-H⋯O and N-H⋯N hydrogen bonds. One of the acetonitrile solvent mol-ecules also lies on a twofold rotation axis.

Related literature

For the crystal structures of related dipicrate metal complexes with 1,3-bis­(1-benzyl-1H-benzimidazol-2-yl)-2-oxapropane ligands, see: Wu, Yun, Li, Wang & Huang (2009 ▶); Wu, Yun, Li, Tao & Wang (2009 ▶).

Experimental

Crystal data

[Co(C16H14N4O)2](C6H2N3O7)2·3C2H3N

M = 1194.93

Monoclinic,

a = 11.4114 (3) Å

b = 9.9303 (2) Å

c = 25.1442 (6) Å

β = 111.164 (1)°

V = 2657.12 (11) Å3

Z = 2

Mo Kα radiation

μ = 0.41 mm−1

T = 153 K

0.28 × 0.25 × 0.17 mm

Data collection

Rigaku R-AXIS Spider diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.894, T max = 0.933

25278 measured reflections

6093 independent reflections

5418 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.087

S = 1.04

6093 reflections

392 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.45 e Å−3

Δρmin = −0.30 e Å−3

Data collection: RAPID-AUTO (Rigaku/MSC, 2004 ▶); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; 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/S1600536809024234/lh2846sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809024234/lh2846Isup2.hkl

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

[Co(C16H14N4O)2](C6H2N3O7)2·3C2H3N	F(000) = 1230
Mr = 1194.93	Dx = 1.494 Mg m−3
Monoclinic, P2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yc	Cell parameters from 7749 reflections
a = 11.4114 (3) Å	θ = 3.2–27.5°
b = 9.9303 (2) Å	µ = 0.41 mm−1
c = 25.1442 (6) Å	T = 153 K
β = 111.164 (1)°	Block, red
V = 2657.12 (11) Å3	0.28 × 0.25 × 0.17 mm
Z = 2

Rigaku R-AXIS Spider diffractometer	6093 independent reflections
Radiation source: fine-focus sealed tube	5418 reflections with I > 2σ(I)
graphite	Rint = 0.021
φ and ω scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −14→14
Tmin = 0.894, Tmax = 0.933	k = −12→12
25278 measured reflections	l = −32→32

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)] = 0.031	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.087	w = 1/[σ2(Fo2) + (0.0487P)2 + 0.9118P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
6093 reflections	Δρmax = 0.45 e Å−3
392 parameters	Δρmin = −0.30 e Å−3
2 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0036 (5)

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	Occ. (<1)
Co	0.5000	0.36301 (2)	0.7500	0.01700 (8)
O1	0.67337 (8)	0.24981 (9)	0.71220 (4)	0.02259 (19)
O2	0.74591 (13)	0.49084 (15)	0.46620 (6)	0.0583 (4)
O3	0.54824 (12)	0.47322 (11)	0.41556 (5)	0.0409 (3)
O4	0.25535 (11)	0.76959 (16)	0.44436 (6)	0.0567 (4)
O5	0.29928 (11)	0.88294 (12)	0.52194 (5)	0.0428 (3)
O6	0.54003 (9)	0.96666 (10)	0.56756 (4)	0.0292 (2)
O7	0.78254 (12)	0.91568 (16)	0.63960 (5)	0.0522 (3)
O8	0.88585 (11)	0.89860 (13)	0.58266 (5)	0.0420 (3)
N1	0.41234 (10)	0.25020 (10)	0.67914 (4)	0.0200 (2)
N2	0.39034 (10)	0.10735 (11)	0.60795 (4)	0.0202 (2)
N3	0.62918 (10)	0.49981 (11)	0.74562 (4)	0.0195 (2)
N4	0.77113 (11)	0.58828 (12)	0.71442 (5)	0.0260 (2)
N5	0.63674 (13)	0.52737 (13)	0.45326 (5)	0.0342 (3)
N6	0.33090 (11)	0.81256 (13)	0.48951 (5)	0.0309 (3)
N7	0.79113 (12)	0.88240 (13)	0.59422 (5)	0.0332 (3)
N8	0.93174 (15)	0.59702 (16)	0.64743 (6)	0.0452 (4)
N9	1.0000	0.3626 (2)	0.7500	0.0471 (5)
C1	0.28403 (12)	0.23999 (12)	0.64561 (5)	0.0196 (2)
C2	0.17845 (12)	0.29913 (14)	0.65151 (5)	0.0252 (3)
H2	0.1860	0.3604	0.6816	0.030*
C3	0.06220 (13)	0.26482 (15)	0.61173 (6)	0.0282 (3)
H3	−0.0113	0.3029	0.6150	0.034*
C4	0.04975 (13)	0.17528 (15)	0.56674 (6)	0.0278 (3)
H4	−0.0317	0.1546	0.5402	0.033*
C5	0.15352 (13)	0.11673 (14)	0.56030 (6)	0.0249 (3)
H5	0.1458	0.0568	0.5298	0.030*
C6	0.26998 (12)	0.14996 (12)	0.60080 (5)	0.0194 (2)
C7	0.47004 (12)	0.16761 (12)	0.65481 (5)	0.0197 (2)
C8	0.60830 (12)	0.13872 (13)	0.67854 (6)	0.0252 (3)
H8A	0.6244	0.0564	0.7023	0.030*
H8B	0.6391	0.1231	0.6469	0.030*
C9	0.68619 (12)	0.35957 (13)	0.67806 (5)	0.0222 (3)
H9A	0.6121	0.3650	0.6422	0.027*
H9B	0.7624	0.3481	0.6684	0.027*
C10	0.69630 (11)	0.48306 (13)	0.71274 (5)	0.0201 (2)
C11	0.75372 (13)	0.68185 (14)	0.75169 (6)	0.0267 (3)
C12	0.80865 (17)	0.80687 (16)	0.77019 (7)	0.0396 (4)
H12	0.8685	0.8446	0.7562	0.047*
C13	0.77203 (19)	0.87304 (16)	0.80967 (8)	0.0450 (4)
H13	0.8071	0.9588	0.8232	0.054*
C14	0.68394 (17)	0.81668 (16)	0.83043 (7)	0.0393 (4)
H14	0.6612	0.8653	0.8578	0.047*
C15	0.62941 (14)	0.69269 (15)	0.81217 (6)	0.0293 (3)
H15	0.5702	0.6549	0.8265	0.035*
C16	0.66544 (13)	0.62542 (13)	0.77169 (5)	0.0221 (3)
C17	0.61070 (14)	0.63884 (13)	0.48431 (6)	0.0262 (3)
C18	0.48772 (13)	0.67268 (13)	0.47497 (5)	0.0238 (3)
H18	0.4208	0.6222	0.4489	0.029*
C19	0.46257 (13)	0.78010 (13)	0.50371 (5)	0.0233 (3)
C20	0.55850 (13)	0.86220 (13)	0.54417 (5)	0.0228 (3)
C21	0.68386 (13)	0.81456 (14)	0.55233 (6)	0.0260 (3)
C22	0.70968 (14)	0.71058 (15)	0.52261 (6)	0.0288 (3)
H22	0.7941	0.6878	0.5281	0.035*
C23	1.05744 (17)	0.6226 (2)	0.58074 (8)	0.0495 (5)
H23A	1.0127	0.5755	0.5449	0.059*
H23B	1.1415	0.5837	0.5987	0.059*
H23C	1.0648	0.7183	0.5730	0.059*
C24	0.98832 (15)	0.60810 (18)	0.61876 (7)	0.0371 (4)
C25	1.0000	0.1051 (3)	0.7500	0.0971 (16)
H25A	1.0691	0.0722	0.7836	0.116*	0.50
H25B	1.0110	0.0722	0.7154	0.116*	0.50
H25C	0.9199	0.0722	0.7511	0.116*	0.50
C26	1.0000	0.2497 (2)	0.7500	0.0355 (5)
H2N	0.4130 (16)	0.0525 (15)	0.5871 (7)	0.037 (5)*
H4N	0.8242 (14)	0.5947 (19)	0.6975 (7)	0.041 (5)*

	U11	U22	U33	U12	U13	U23
Co	0.01758 (12)	0.01751 (13)	0.01522 (12)	0.000	0.00511 (9)	0.000
O1	0.0227 (5)	0.0215 (4)	0.0208 (4)	−0.0016 (3)	0.0046 (4)	−0.0025 (3)
O2	0.0533 (8)	0.0616 (9)	0.0637 (8)	0.0260 (7)	0.0257 (7)	−0.0152 (7)
O3	0.0612 (8)	0.0328 (6)	0.0310 (5)	0.0086 (5)	0.0194 (5)	−0.0069 (5)
O4	0.0274 (6)	0.0785 (10)	0.0554 (8)	−0.0016 (6)	0.0044 (6)	−0.0380 (7)
O5	0.0291 (6)	0.0489 (7)	0.0506 (7)	0.0037 (5)	0.0147 (5)	−0.0249 (6)
O6	0.0275 (5)	0.0275 (5)	0.0321 (5)	0.0021 (4)	0.0102 (4)	−0.0101 (4)
O7	0.0354 (6)	0.0790 (10)	0.0353 (6)	0.0055 (6)	0.0046 (5)	−0.0223 (6)
O8	0.0292 (6)	0.0469 (7)	0.0486 (7)	−0.0026 (5)	0.0126 (5)	0.0015 (5)
N1	0.0186 (5)	0.0204 (5)	0.0200 (5)	0.0016 (4)	0.0058 (4)	−0.0023 (4)
N2	0.0214 (5)	0.0189 (5)	0.0203 (5)	0.0001 (4)	0.0075 (4)	−0.0037 (4)
N3	0.0211 (5)	0.0207 (5)	0.0178 (5)	−0.0001 (4)	0.0082 (4)	−0.0005 (4)
N4	0.0287 (6)	0.0261 (6)	0.0286 (6)	−0.0045 (5)	0.0170 (5)	−0.0010 (5)
N5	0.0495 (8)	0.0292 (6)	0.0304 (6)	0.0138 (6)	0.0222 (6)	0.0023 (5)
N6	0.0251 (6)	0.0324 (6)	0.0345 (6)	0.0000 (5)	0.0100 (5)	−0.0109 (5)
N7	0.0271 (6)	0.0361 (7)	0.0327 (6)	0.0065 (5)	0.0061 (5)	−0.0024 (5)
N8	0.0477 (9)	0.0524 (9)	0.0459 (8)	0.0125 (7)	0.0295 (7)	0.0123 (7)
N9	0.0421 (12)	0.0387 (12)	0.0568 (13)	0.000	0.0132 (10)	0.000
C1	0.0192 (6)	0.0204 (6)	0.0178 (5)	−0.0006 (5)	0.0052 (5)	−0.0001 (4)
C2	0.0217 (6)	0.0300 (7)	0.0234 (6)	0.0023 (5)	0.0074 (5)	−0.0052 (5)
C3	0.0199 (6)	0.0351 (7)	0.0289 (7)	0.0021 (5)	0.0080 (5)	−0.0046 (6)
C4	0.0203 (6)	0.0330 (7)	0.0259 (6)	−0.0026 (5)	0.0035 (5)	−0.0040 (6)
C5	0.0247 (7)	0.0264 (6)	0.0215 (6)	−0.0022 (5)	0.0059 (5)	−0.0051 (5)
C6	0.0204 (6)	0.0191 (6)	0.0196 (5)	−0.0003 (4)	0.0082 (5)	0.0008 (4)
C7	0.0212 (6)	0.0167 (5)	0.0209 (6)	−0.0001 (5)	0.0073 (5)	−0.0009 (4)
C8	0.0206 (6)	0.0220 (6)	0.0294 (6)	0.0019 (5)	0.0049 (5)	−0.0078 (5)
C9	0.0217 (6)	0.0264 (7)	0.0198 (6)	0.0004 (5)	0.0091 (5)	−0.0015 (5)
C10	0.0189 (6)	0.0239 (6)	0.0179 (5)	0.0011 (5)	0.0073 (5)	0.0026 (5)
C11	0.0299 (7)	0.0246 (7)	0.0280 (6)	−0.0030 (5)	0.0133 (6)	−0.0004 (5)
C12	0.0469 (9)	0.0293 (8)	0.0490 (9)	−0.0132 (7)	0.0251 (8)	−0.0049 (7)
C13	0.0582 (11)	0.0270 (8)	0.0540 (10)	−0.0149 (7)	0.0254 (9)	−0.0139 (7)
C14	0.0509 (10)	0.0305 (8)	0.0415 (8)	−0.0047 (7)	0.0228 (8)	−0.0134 (7)
C15	0.0347 (8)	0.0284 (7)	0.0283 (6)	−0.0023 (6)	0.0156 (6)	−0.0056 (6)
C16	0.0240 (6)	0.0213 (6)	0.0211 (6)	−0.0010 (5)	0.0080 (5)	−0.0001 (5)
C17	0.0380 (8)	0.0225 (6)	0.0229 (6)	0.0085 (5)	0.0168 (6)	0.0030 (5)
C18	0.0335 (7)	0.0202 (6)	0.0203 (6)	0.0012 (5)	0.0130 (5)	0.0008 (5)
C19	0.0259 (7)	0.0229 (6)	0.0229 (6)	0.0037 (5)	0.0111 (5)	−0.0006 (5)
C20	0.0256 (7)	0.0230 (6)	0.0216 (6)	0.0032 (5)	0.0106 (5)	0.0002 (5)
C21	0.0252 (7)	0.0282 (7)	0.0238 (6)	0.0038 (5)	0.0081 (5)	0.0003 (5)
C22	0.0287 (7)	0.0332 (7)	0.0269 (6)	0.0109 (6)	0.0129 (6)	0.0036 (6)
C23	0.0350 (9)	0.0802 (14)	0.0412 (9)	0.0146 (9)	0.0233 (8)	0.0109 (9)
C24	0.0319 (8)	0.0471 (9)	0.0344 (8)	0.0142 (7)	0.0146 (7)	0.0100 (7)
C25	0.109 (3)	0.0309 (15)	0.110 (3)	0.000	−0.011 (3)	0.000
C26	0.0263 (10)	0.0338 (12)	0.0407 (11)	0.000	0.0052 (9)	0.000

Co—N1	2.0355 (10)	C4—H4	0.9500
Co—N1i	2.0355 (10)	C5—C6	1.3910 (18)
Co—N3	2.0367 (11)	C5—H5	0.9500
Co—N3i	2.0367 (11)	C7—C8	1.4993 (18)
O1—C8	1.4250 (15)	C8—H8A	0.9900
O1—C9	1.4272 (16)	C8—H8B	0.9900
O2—N5	1.2234 (19)	C9—C10	1.4849 (18)
O3—N5	1.2315 (18)	C9—H9A	0.9900
O4—N6	1.2278 (17)	C9—H9B	0.9900
O5—N6	1.2233 (16)	C11—C12	1.393 (2)
O6—C20	1.2475 (16)	C11—C16	1.3956 (19)
O7—N7	1.2255 (17)	C12—C13	1.375 (2)
O8—N7	1.2270 (17)	C12—H12	0.9500
N1—C7	1.3308 (16)	C13—C14	1.405 (3)
N1—C1	1.4048 (16)	C13—H13	0.9500
N2—C7	1.3416 (16)	C14—C15	1.381 (2)
N2—C6	1.3855 (16)	C14—H14	0.9500
N2—H2N	0.858 (9)	C15—C16	1.3977 (19)
N3—C10	1.3247 (15)	C15—H15	0.9500
N3—C16	1.4004 (16)	C17—C18	1.378 (2)
N4—C10	1.3404 (17)	C17—C22	1.388 (2)
N4—C11	1.3840 (18)	C18—C19	1.3756 (18)
N4—H4N	0.858 (9)	C18—H18	0.9500
N5—C17	1.4459 (17)	C19—C20	1.4469 (19)
N6—C19	1.4497 (18)	C20—C21	1.4492 (19)
N7—C21	1.4597 (19)	C21—C22	1.368 (2)
N8—C24	1.133 (2)	C22—H22	0.9500
N9—C26	1.121 (3)	C23—C24	1.450 (2)
C1—C2	1.3956 (18)	C23—H23A	0.9800
C1—C6	1.4013 (17)	C23—H23B	0.9800
C2—C3	1.3850 (19)	C23—H23C	0.9800
C2—H2	0.9500	C25—C26	1.436 (4)
C3—C4	1.405 (2)	C25—H25A	0.9800
C3—H3	0.9500	C25—H25B	0.9800
C4—C5	1.380 (2)	C25—H25C	0.9800
N1—Co—N1i	113.22 (6)	C10—C9—H9A	110.5
N1—Co—N3	117.15 (4)	O1—C9—H9B	110.5
N1i—Co—N3	106.14 (4)	C10—C9—H9B	110.5
N1—Co—N3i	106.13 (4)	H9A—C9—H9B	108.7
N1i—Co—N3i	117.15 (4)	N3—C10—N4	112.81 (11)
N3—Co—N3i	96.33 (6)	N3—C10—C9	122.03 (11)
C8—O1—C9	112.25 (10)	N4—C10—C9	125.15 (11)
C7—N1—C1	105.13 (10)	N4—C11—C12	131.85 (13)
C7—N1—Co	124.97 (9)	N4—C11—C16	105.85 (12)
C1—N1—Co	129.90 (8)	C12—C11—C16	122.27 (13)
C7—N2—C6	107.67 (10)	C13—C12—C11	116.71 (15)
C7—N2—H2N	124.2 (12)	C13—C12—H12	121.6
C6—N2—H2N	128.2 (12)	C11—C12—H12	121.6
C10—N3—C16	105.33 (10)	C12—C13—C14	121.49 (14)
C10—N3—Co	122.88 (9)	C12—C13—H13	119.3
C16—N3—Co	131.77 (8)	C14—C13—H13	119.3
C10—N4—C11	107.41 (11)	C15—C14—C13	121.90 (14)
C10—N4—H4N	126.7 (13)	C15—C14—H14	119.0
C11—N4—H4N	125.8 (13)	C13—C14—H14	119.0
O2—N5—O3	123.27 (13)	C14—C15—C16	116.89 (14)
O2—N5—C17	118.13 (14)	C14—C15—H15	121.6
O3—N5—C17	118.60 (13)	C16—C15—H15	121.6
O5—N6—O4	122.50 (13)	C11—C16—C15	120.73 (13)
O5—N6—C19	119.46 (12)	C11—C16—N3	108.58 (11)
O4—N6—C19	118.03 (12)	C15—C16—N3	130.67 (12)
O7—N7—O8	123.97 (14)	C18—C17—C22	121.11 (12)
O7—N7—C21	117.91 (13)	C18—C17—N5	119.33 (13)
O8—N7—C21	118.07 (12)	C22—C17—N5	119.56 (13)
C2—C1—C6	120.09 (12)	C19—C18—C17	119.49 (13)
C2—C1—N1	131.19 (11)	C19—C18—H18	120.3
C6—C1—N1	108.69 (11)	C17—C18—H18	120.3
C3—C2—C1	117.27 (12)	C18—C19—C20	123.90 (12)
C3—C2—H2	121.4	C18—C19—N6	115.93 (12)
C1—C2—H2	121.4	C20—C19—N6	120.12 (11)
C2—C3—C4	121.95 (13)	O6—C20—C19	125.89 (12)
C2—C3—H3	119.0	O6—C20—C21	122.06 (13)
C4—C3—H3	119.0	C19—C20—C21	111.92 (11)
C5—C4—C3	121.29 (12)	C22—C21—C20	124.43 (13)
C5—C4—H4	119.4	C22—C21—N7	116.92 (13)
C3—C4—H4	119.4	C20—C21—N7	118.64 (12)
C4—C5—C6	116.58 (12)	C21—C22—C17	119.00 (13)
C4—C5—H5	121.7	C21—C22—H22	120.5
C6—C5—H5	121.7	C17—C22—H22	120.5
N2—C6—C5	131.51 (12)	C24—C23—H23A	109.5
N2—C6—C1	105.68 (11)	C24—C23—H23B	109.5
C5—C6—C1	122.80 (12)	H23A—C23—H23B	109.5
N1—C7—N2	112.80 (11)	C24—C23—H23C	109.5
N1—C7—C8	124.00 (11)	H23A—C23—H23C	109.5
N2—C7—C8	123.12 (11)	H23B—C23—H23C	109.5
O1—C8—C7	109.64 (10)	N8—C24—C23	178.40 (18)
O1—C8—H8A	109.7	C26—C25—H25A	109.5
C7—C8—H8A	109.7	C26—C25—H25B	109.5
O1—C8—H8B	109.7	H25A—C25—H25B	109.5
C7—C8—H8B	109.7	C26—C25—H25C	109.5
H8A—C8—H8B	108.2	H25A—C25—H25C	109.5
O1—C9—C10	106.29 (10)	H25B—C25—H25C	109.5
O1—C9—H9A	110.5	N9—C26—C25	180.000 (3)
N1i—Co—N1—C7	−63.92 (10)	O1—C9—C10—N4	141.87 (12)
N3—Co—N1—C7	60.12 (11)	C10—N4—C11—C12	178.52 (17)
N3i—Co—N1—C7	166.22 (10)	C10—N4—C11—C16	0.22 (15)
N1i—Co—N1—C1	116.01 (11)	N4—C11—C12—C13	−177.85 (17)
N3—Co—N1—C1	−119.95 (10)	C16—C11—C12—C13	0.2 (3)
N3i—Co—N1—C1	−13.86 (11)	C11—C12—C13—C14	0.3 (3)
N1—Co—N3—C10	−29.43 (11)	C12—C13—C14—C15	−0.3 (3)
N1i—Co—N3—C10	98.12 (10)	C13—C14—C15—C16	−0.3 (3)
N3i—Co—N3—C10	−141.21 (11)	N4—C11—C16—C15	177.74 (13)
N1—Co—N3—C16	148.33 (10)	C12—C11—C16—C15	−0.8 (2)
N1i—Co—N3—C16	−84.11 (11)	N4—C11—C16—N3	−0.97 (15)
N3i—Co—N3—C16	36.55 (10)	C12—C11—C16—N3	−179.47 (14)
C7—N1—C1—C2	177.34 (14)	C14—C15—C16—C11	0.8 (2)
Co—N1—C1—C2	−2.6 (2)	C14—C15—C16—N3	179.14 (14)
C7—N1—C1—C6	−0.67 (13)	C10—N3—C16—C11	1.34 (14)
Co—N1—C1—C6	179.40 (8)	Co—N3—C16—C11	−176.71 (9)
C6—C1—C2—C3	0.0 (2)	C10—N3—C16—C15	−177.19 (14)
N1—C1—C2—C3	−177.80 (13)	Co—N3—C16—C15	4.8 (2)
C1—C2—C3—C4	−0.6 (2)	O2—N5—C17—C18	−172.99 (14)
C2—C3—C4—C5	0.3 (2)	O3—N5—C17—C18	6.38 (19)
C3—C4—C5—C6	0.6 (2)	O2—N5—C17—C22	7.5 (2)
C7—N2—C6—C5	−178.36 (14)	O3—N5—C17—C22	−173.11 (13)
C7—N2—C6—C1	0.86 (14)	C22—C17—C18—C19	0.6 (2)
C4—C5—C6—N2	177.88 (13)	N5—C17—C18—C19	−178.90 (12)
C4—C5—C6—C1	−1.2 (2)	C17—C18—C19—C20	−0.1 (2)
C2—C1—C6—N2	−178.38 (12)	C17—C18—C19—N6	177.32 (12)
N1—C1—C6—N2	−0.12 (13)	O5—N6—C19—C18	162.30 (14)
C2—C1—C6—C5	0.92 (19)	O4—N6—C19—C18	−19.0 (2)
N1—C1—C6—C5	179.19 (12)	O5—N6—C19—C20	−20.2 (2)
C1—N1—C7—N2	1.27 (14)	O4—N6—C19—C20	158.52 (15)
Co—N1—C7—N2	−178.79 (8)	C18—C19—C20—O6	173.77 (13)
C1—N1—C7—C8	−175.73 (12)	N6—C19—C20—O6	−3.5 (2)
Co—N1—C7—C8	4.21 (18)	C18—C19—C20—C21	−2.18 (18)
C6—N2—C7—N1	−1.38 (15)	N6—C19—C20—C21	−179.48 (12)
C6—N2—C7—C8	175.65 (12)	O6—C20—C21—C22	−171.77 (14)
C9—O1—C8—C7	−77.34 (13)	C19—C20—C21—C22	4.36 (19)
N1—C7—C8—O1	−26.34 (18)	O6—C20—C21—N7	7.1 (2)
N2—C7—C8—O1	156.97 (11)	C19—C20—C21—N7	−176.76 (12)
C8—O1—C9—C10	153.52 (10)	O7—N7—C21—C22	−140.26 (15)
C16—N3—C10—N4	−1.25 (14)	O8—N7—C21—C22	37.34 (19)
Co—N3—C10—N4	177.02 (8)	O7—N7—C21—C20	40.78 (19)
C16—N3—C10—C9	179.16 (11)	O8—N7—C21—C20	−141.62 (13)
Co—N3—C10—C9	−2.57 (16)	C20—C21—C22—C17	−4.2 (2)
C11—N4—C10—N3	0.67 (15)	N7—C21—C22—C17	176.93 (12)
C11—N4—C10—C9	−179.76 (12)	C18—C17—C22—C21	1.5 (2)
O1—C9—C10—N3	−38.59 (16)	N5—C17—C22—C21	−179.07 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O6ii	0.86 (1)	1.89 (1)	2.6746 (14)	151 (2)
N2—H2N···O5ii	0.86 (1)	2.38 (2)	3.0166 (15)	131 (2)
N4—H4N···N8	0.86 (1)	2.05 (1)	2.9040 (18)	172 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O6i	0.858 (9)	1.893 (12)	2.6746 (14)	150.7 (17)
N2—H2N⋯O5i	0.858 (9)	2.381 (15)	3.0166 (15)	131.3 (15)
N4—H4N⋯N8	0.858 (9)	2.052 (10)	2.9040 (18)	171.8 (18)

Symmetry code: (i) .