(Acetato-κO){bis-[(2,4-dimethyl-1H-pyrazol-1-yl)meth-yl][(pyridin-2-yl)meth-yl]amine}-cobalt(II) hexa-fluorido-phosphate.

In the title compound, [Co(CH(3)CO(2))(C(18)H(24)N(6))]PF(6), the Co(II) atom is penta-coordinated in a distorted trigonal-bipyramidal geometry by four N atoms from a tripodal ligand and one O atom from a monodentate acetate ligand. The crystal packing is stabilized by inter-molecular C-H⋯F and C-H⋯O hydrogen bonds.

Related literature

For related structures, see: Kumar et al. (2012 ▶); Li et al. (2008 ▶); Tao et al. (2006 ▶).

Experimental

Crystal data

[Co(C2H3O2)(C18H24N6)]PF6

M = 587.38

Monoclinic,

a = 13.7489 (6) Å

b = 13.0185 (5) Å

c = 15.4765 (7) Å

β = 115.759 (6)°

V = 2494.9 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.83 mm−1

T = 293 K

0.25 × 0.20 × 0.20 mm

Data collection

Oxford Diffraction Gemini S Ultra diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006 ▶) T min = 0.820, T max = 0.852

19458 measured reflections

4890 independent reflections

3136 reflections with I > 2σ(I)

R int = 0.056

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.129

S = 0.97

4890 reflections

325 parameters

H-atom parameters constrained

Δρmax = 0.76 e Å−3

Δρmin = −0.39 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812035222/hy2569sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812035222/hy2569Isup2.hkl

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

[Co(C2H3O2)(C18H24N6)]PF6	F(000) = 1204
Mr = 587.38	Dx = 1.564 Mg m−3Dm = 1.564 Mg m−3Dm measured by not measured
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4897 reflections
a = 13.7489 (6) Å	θ = 2.1–26.0°
b = 13.0185 (5) Å	µ = 0.83 mm−1
c = 15.4765 (7) Å	T = 293 K
β = 115.759 (6)°	Block, green
V = 2494.9 (2) Å3	0.25 × 0.20 × 0.20 mm
Z = 4

Oxford Diffraction Gemini S Ultra diffractometer	4890 independent reflections
Radiation source: fine-focus sealed tube	3136 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.056
Detector resolution: 0 pixels mm-1	θmax = 26.0°, θmin = 2.1°
ω scans	h = −16→16
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	k = −16→15
Tmin = 0.820, Tmax = 0.852	l = −18→19
19458 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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129	H-atom parameters constrained
S = 0.97	w = 1/[σ2(Fo2) + (0.069P)2] where P = (Fo2 + 2Fc2)/3
4890 reflections	(Δ/σ)max = 0.001
325 parameters	Δρmax = 0.76 e Å−3
0 restraints	Δρmin = −0.39 e Å−3

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	0.21796 (4)	0.72452 (4)	0.09330 (3)	0.02612 (16)
O1	0.1832 (2)	0.7956 (2)	0.19132 (18)	0.0382 (7)
O2	0.1668 (2)	0.6300 (2)	0.20698 (19)	0.0392 (7)
N2	0.2747 (2)	0.6622 (2)	−0.0162 (2)	0.0273 (7)
N3	0.2597 (2)	0.8535 (2)	0.0399 (2)	0.0287 (7)
N1	0.3582 (2)	0.6391 (2)	0.1721 (2)	0.0311 (8)
N4	0.3193 (2)	0.8376 (3)	−0.0096 (2)	0.0320 (8)
C8	0.1624 (3)	0.7190 (4)	0.2326 (3)	0.0350 (9)
N6	0.0781 (2)	0.6710 (2)	−0.0169 (2)	0.0290 (7)
N5	0.0880 (2)	0.6312 (2)	−0.0950 (2)	0.0276 (7)
C11	−0.0037 (3)	0.5858 (3)	−0.1566 (2)	0.0286 (9)
C12	−0.0753 (3)	0.5944 (3)	−0.1181 (3)	0.0358 (10)
H12A	−0.1457	0.5697	−0.1443	0.043*
C14	0.3562 (3)	0.7344 (3)	−0.0146 (3)	0.0367 (10)
H14A	0.4243	0.7212	0.0406	0.044*
H14B	0.3671	0.7266	−0.0721	0.044*
C16	0.3396 (3)	0.9270 (3)	−0.0439 (3)	0.0385 (11)
C17	−0.0226 (3)	0.6476 (3)	−0.0316 (3)	0.0309 (9)
C18	0.5017 (4)	0.5877 (4)	0.3187 (3)	0.0523 (12)
H18A	0.5413	0.5969	0.3845	0.063*
C19	0.3871 (3)	0.5661 (3)	0.1266 (3)	0.0304 (9)
C20	0.3210 (3)	0.5617 (3)	0.0205 (3)	0.0380 (10)
H20A	0.3659	0.5399	−0.0100	0.046*
H20B	0.2635	0.5117	0.0054	0.046*
C22	0.2900 (3)	1.0021 (3)	−0.0151 (3)	0.0375 (10)
H22A	0.2892	1.0721	−0.0275	0.045*
C23	0.4712 (3)	0.5003 (3)	0.1747 (3)	0.0386 (10)
H23A	0.4893	0.4490	0.1424	0.046*
C24	0.1742 (3)	1.0008 (3)	0.0794 (3)	0.0415 (10)
H24A	0.1512	0.9482	0.1100	0.062*
H24B	0.1120	1.0331	0.0302	0.062*
H24C	0.2160	1.0511	0.1262	0.062*
C25	0.1813 (3)	0.6592 (3)	−0.1093 (2)	0.0304 (9)
H25A	0.1704	0.7259	−0.1400	0.036*
H25B	0.1929	0.6092	−0.1504	0.036*
C27	0.4164 (3)	0.6493 (3)	0.2672 (3)	0.0422 (11)
H27A	0.3976	0.7006	0.2990	0.051*
C29	−0.0650 (3)	0.6777 (4)	0.0380 (3)	0.0454 (11)
H29A	−0.0098	0.7133	0.0909	0.068*
H29B	−0.0864	0.6174	0.0610	0.068*
H29C	−0.1263	0.7220	0.0070	0.068*
C30	0.2412 (3)	0.9542 (3)	0.0360 (2)	0.0326 (9)
C31	0.1285 (4)	0.7417 (4)	0.3103 (3)	0.0557 (13)
H31A	0.1158	0.6784	0.3356	0.083*
H31B	0.0633	0.7817	0.2845	0.083*
H31C	0.1845	0.7796	0.3606	0.083*
C32	−0.0137 (3)	0.5399 (3)	−0.2481 (3)	0.0400 (10)
H32A	0.0538	0.5466	−0.2522	0.060*
H32B	−0.0692	0.5749	−0.3012	0.060*
H32C	−0.0320	0.4685	−0.2501	0.060*
C33	0.5278 (4)	0.5124 (4)	0.2721 (3)	0.0517 (12)
H33A	0.5849	0.4684	0.3066	0.062*
C34	0.4055 (4)	0.9310 (4)	−0.0981 (3)	0.0571 (14)
H34A	0.4268	0.8626	−0.1058	0.086*
H34B	0.4687	0.9720	−0.0637	0.086*
H34C	0.3638	0.9608	−0.1601	0.086*
P1	0.69225 (8)	0.70775 (8)	0.13886 (8)	0.0368 (3)
F1	0.7752 (2)	0.6167 (2)	0.15406 (17)	0.0589 (7)
F2	0.6097 (2)	0.7997 (2)	0.1226 (2)	0.0752 (9)
F3	0.5946 (2)	0.6330 (2)	0.0763 (2)	0.0796 (10)
F4	0.6815 (3)	0.6735 (3)	0.2316 (2)	0.0923 (11)
F5	0.7866 (3)	0.7796 (3)	0.2033 (3)	0.1060 (13)
F6	0.7016 (3)	0.7399 (3)	0.0464 (3)	0.1068 (13)

	U11	U22	U33	U12	U13	U23
Co1	0.0261 (3)	0.0290 (3)	0.0229 (3)	−0.0040 (2)	0.0103 (2)	−0.0024 (2)
O1	0.0510 (17)	0.0346 (17)	0.0341 (15)	0.0009 (14)	0.0231 (14)	0.0000 (12)
O2	0.0412 (16)	0.0356 (18)	0.0438 (16)	−0.0021 (13)	0.0211 (14)	−0.0069 (13)
N2	0.0231 (16)	0.0316 (19)	0.0258 (16)	−0.0044 (14)	0.0093 (13)	−0.0033 (13)
N3	0.0262 (17)	0.033 (2)	0.0258 (16)	−0.0050 (14)	0.0100 (14)	−0.0013 (14)
N1	0.0248 (16)	0.035 (2)	0.0309 (18)	−0.0048 (15)	0.0095 (14)	0.0015 (15)
N4	0.0297 (17)	0.039 (2)	0.0273 (17)	−0.0063 (16)	0.0128 (15)	−0.0020 (15)
C8	0.035 (2)	0.043 (3)	0.028 (2)	0.004 (2)	0.0141 (18)	−0.001 (2)
N6	0.0283 (17)	0.0369 (19)	0.0254 (16)	−0.0029 (15)	0.0149 (14)	−0.0038 (14)
N5	0.0250 (16)	0.0351 (19)	0.0242 (16)	−0.0030 (14)	0.0121 (14)	−0.0025 (14)
C11	0.027 (2)	0.033 (2)	0.0201 (18)	−0.0039 (18)	0.0045 (16)	0.0027 (16)
C12	0.025 (2)	0.046 (3)	0.033 (2)	−0.0070 (19)	0.0093 (17)	0.0034 (19)
C14	0.029 (2)	0.049 (3)	0.037 (2)	−0.008 (2)	0.0192 (18)	−0.002 (2)
C16	0.037 (2)	0.050 (3)	0.023 (2)	−0.026 (2)	0.0076 (18)	0.0008 (19)
C17	0.027 (2)	0.034 (2)	0.031 (2)	−0.0021 (18)	0.0127 (18)	0.0024 (18)
C18	0.040 (3)	0.066 (3)	0.043 (3)	−0.007 (3)	0.010 (2)	0.016 (2)
C19	0.025 (2)	0.029 (2)	0.037 (2)	−0.0042 (17)	0.0132 (17)	−0.0003 (18)
C20	0.034 (2)	0.041 (3)	0.035 (2)	−0.005 (2)	0.0122 (19)	−0.0072 (19)
C22	0.044 (2)	0.032 (2)	0.029 (2)	−0.016 (2)	0.008 (2)	−0.0007 (18)
C23	0.033 (2)	0.034 (2)	0.047 (3)	0.0022 (19)	0.016 (2)	0.004 (2)
C24	0.044 (2)	0.036 (3)	0.042 (2)	0.000 (2)	0.016 (2)	−0.0003 (19)
C25	0.026 (2)	0.042 (2)	0.0239 (19)	−0.0047 (18)	0.0116 (17)	−0.0029 (17)
C27	0.035 (2)	0.052 (3)	0.035 (2)	−0.009 (2)	0.012 (2)	0.010 (2)
C29	0.032 (2)	0.067 (3)	0.040 (2)	−0.002 (2)	0.018 (2)	0.000 (2)
C30	0.031 (2)	0.032 (2)	0.024 (2)	−0.0073 (18)	0.0017 (17)	−0.0019 (17)
C31	0.085 (4)	0.053 (3)	0.046 (3)	0.015 (3)	0.043 (3)	0.004 (2)
C32	0.036 (2)	0.052 (3)	0.030 (2)	−0.009 (2)	0.0133 (18)	−0.0087 (19)
C33	0.039 (3)	0.051 (3)	0.062 (3)	0.006 (2)	0.020 (2)	0.022 (3)
C34	0.067 (3)	0.070 (4)	0.043 (3)	−0.036 (3)	0.032 (2)	−0.012 (2)
P1	0.0359 (6)	0.0387 (7)	0.0379 (6)	0.0048 (5)	0.0180 (5)	0.0024 (5)
F1	0.0548 (16)	0.0618 (18)	0.0536 (16)	0.0247 (14)	0.0175 (13)	0.0043 (13)
F2	0.0545 (17)	0.0558 (19)	0.101 (2)	0.0191 (14)	0.0206 (17)	−0.0136 (16)
F3	0.0486 (17)	0.066 (2)	0.113 (2)	−0.0015 (15)	0.0257 (17)	−0.0362 (18)
F4	0.140 (3)	0.093 (2)	0.084 (2)	0.008 (2)	0.085 (2)	0.0041 (19)
F5	0.0547 (19)	0.074 (2)	0.152 (3)	−0.0146 (18)	0.010 (2)	−0.037 (2)
F6	0.134 (3)	0.131 (3)	0.087 (2)	0.051 (3)	0.078 (2)	0.060 (2)

Co1—O1	2.004 (3)	C19—C20	1.493 (5)
Co1—N6	2.059 (3)	C20—H20A	0.9700
Co1—N3	2.060 (3)	C20—H20B	0.9700
Co1—N1	2.097 (3)	C22—C30	1.388 (5)
Co1—N2	2.298 (3)	C22—H22A	0.9300
O1—C8	1.281 (5)	C23—C33	1.373 (6)
O2—C8	1.234 (5)	C23—H23A	0.9300
N2—C14	1.455 (5)	C24—C30	1.485 (5)
N2—C25	1.456 (4)	C24—H24A	0.9600
N2—C20	1.458 (5)	C24—H24B	0.9600
N3—C30	1.332 (5)	C24—H24C	0.9600
N3—N4	1.359 (4)	C25—H25A	0.9700
N1—C19	1.342 (5)	C25—H25B	0.9700
N1—C27	1.342 (5)	C27—H27A	0.9300
N4—C16	1.357 (5)	C29—H29A	0.9600
N4—C14	1.450 (5)	C29—H29B	0.9600
C8—C31	1.497 (5)	C29—H29C	0.9600
N6—C17	1.337 (5)	C31—H31A	0.9600
N6—N5	1.375 (4)	C31—H31B	0.9600
N5—C11	1.344 (4)	C31—H31C	0.9600
N5—C25	1.441 (4)	C32—H32A	0.9600
C11—C12	1.358 (5)	C32—H32B	0.9600
C11—C32	1.488 (5)	C32—H32C	0.9600
C12—C17	1.398 (5)	C33—H33A	0.9300
C12—H12A	0.9300	C34—H34A	0.9600
C14—H14A	0.9700	C34—H34B	0.9600
C14—H14B	0.9700	C34—H34C	0.9600
C16—C22	1.373 (6)	P1—F6	1.549 (3)
C16—C34	1.480 (6)	P1—F5	1.558 (3)
C17—C29	1.483 (5)	P1—F4	1.570 (3)
C18—C33	1.355 (7)	P1—F1	1.590 (3)
C18—C27	1.357 (6)	P1—F2	1.592 (3)
C18—H18A	0.9300	P1—F3	1.600 (3)
C19—C23	1.369 (5)
O1—Co1—N6	109.80 (11)	C16—C22—H22A	126.4
O1—Co1—N3	97.31 (12)	C30—C22—H22A	126.4
N6—Co1—N3	105.45 (12)	C19—C23—C33	117.8 (4)
O1—Co1—N1	105.43 (12)	C19—C23—H23A	121.1
N6—Co1—N1	126.43 (12)	C33—C23—H23A	121.1
N3—Co1—N1	108.63 (12)	C30—C24—H24A	109.5
O1—Co1—N2	171.77 (11)	C30—C24—H24B	109.5
N6—Co1—N2	76.38 (11)	H24A—C24—H24B	109.5
N3—Co1—N2	75.47 (12)	C30—C24—H24C	109.5
N1—Co1—N2	73.78 (11)	H24A—C24—H24C	109.5
C8—O1—Co1	101.3 (2)	H24B—C24—H24C	109.5
C14—N2—C25	112.0 (3)	N5—C25—N2	108.3 (3)
C14—N2—C20	111.7 (3)	N5—C25—H25A	110.0
C25—N2—C20	114.1 (3)	N2—C25—H25A	110.0
C14—N2—Co1	105.4 (2)	N5—C25—H25B	110.0
C25—N2—Co1	107.7 (2)	N2—C25—H25B	110.0
C20—N2—Co1	105.1 (2)	H25A—C25—H25B	108.4
C30—N3—N4	105.9 (3)	N1—C27—C18	122.5 (4)
C30—N3—Co1	137.6 (3)	N1—C27—H27A	118.7
N4—N3—Co1	116.3 (2)	C18—C27—H27A	118.7
C19—N1—C27	118.2 (3)	C17—C29—H29A	109.5
C19—N1—Co1	118.6 (2)	C17—C29—H29B	109.5
C27—N1—Co1	123.0 (3)	H29A—C29—H29B	109.5
C16—N4—N3	111.5 (3)	C17—C29—H29C	109.5
C16—N4—C14	129.6 (3)	H29A—C29—H29C	109.5
N3—N4—C14	118.8 (3)	H29B—C29—H29C	109.5
O2—C8—O1	121.2 (4)	N3—C30—C22	109.7 (4)
O2—C8—C31	121.3 (4)	N3—C30—C24	121.7 (3)
O1—C8—C31	117.5 (4)	C22—C30—C24	128.5 (4)
C17—N6—N5	104.8 (3)	C8—C31—H31A	109.5
C17—N6—Co1	138.1 (2)	C8—C31—H31B	109.5
N5—N6—Co1	116.2 (2)	H31A—C31—H31B	109.5
C11—N5—N6	111.7 (3)	C8—C31—H31C	109.5
C11—N5—C25	128.7 (3)	H31A—C31—H31C	109.5
N6—N5—C25	118.4 (3)	H31B—C31—H31C	109.5
N5—C11—C12	106.7 (3)	C11—C32—H32A	109.5
N5—C11—C32	121.5 (3)	C11—C32—H32B	109.5
C12—C11—C32	131.8 (3)	H32A—C32—H32B	109.5
C11—C12—C17	106.8 (3)	C11—C32—H32C	109.5
C11—C12—H12A	126.6	H32A—C32—H32C	109.5
C17—C12—H12A	126.6	H32B—C32—H32C	109.5
N4—C14—N2	108.3 (3)	C18—C33—C23	120.9 (4)
N4—C14—H14A	110.0	C18—C33—H33A	119.6
N2—C14—H14A	110.0	C23—C33—H33A	119.6
N4—C14—H14B	110.0	C16—C34—H34A	109.5
N2—C14—H14B	110.0	C16—C34—H34B	109.5
H14A—C14—H14B	108.4	H34A—C34—H34B	109.5
N4—C16—C22	105.6 (3)	C16—C34—H34C	109.5
N4—C16—C34	122.1 (4)	H34A—C34—H34C	109.5
C22—C16—C34	132.3 (4)	H34B—C34—H34C	109.5
N6—C17—C12	110.1 (3)	F6—P1—F5	92.8 (2)
N6—C17—C29	121.4 (3)	F6—P1—F4	179.0 (2)
C12—C17—C29	128.5 (3)	F5—P1—F4	88.2 (2)
C33—C18—C27	118.4 (4)	F6—P1—F1	89.78 (17)
C33—C18—H18A	120.8	F5—P1—F1	90.48 (17)
C27—C18—H18A	120.8	F4—P1—F1	89.95 (17)
N1—C19—C23	122.1 (4)	F6—P1—F2	89.42 (18)
N1—C19—C20	115.2 (3)	F5—P1—F2	89.31 (17)
C23—C19—C20	122.7 (4)	F4—P1—F2	90.85 (18)
N2—C20—C19	110.4 (3)	F1—P1—F2	179.16 (18)
N2—C20—H20A	109.6	F6—P1—F3	89.5 (2)
C19—C20—H20A	109.6	F5—P1—F3	177.7 (2)
N2—C20—H20B	109.6	F4—P1—F3	89.55 (19)
C19—C20—H20B	109.6	F1—P1—F3	89.76 (15)
H20A—C20—H20B	108.1	F2—P1—F3	90.48 (15)
C16—C22—C30	107.2 (4)
N6—Co1—O1—C8	74.4 (2)	N6—N5—C11—C32	178.1 (3)
N3—Co1—O1—C8	−176.2 (2)	C25—N5—C11—C32	11.1 (6)
N1—Co1—O1—C8	−64.5 (2)	N5—C11—C12—C17	0.5 (4)
N6—Co1—N2—C14	141.2 (2)	C32—C11—C12—C17	−178.2 (4)
N3—Co1—N2—C14	31.0 (2)	C16—N4—C14—N2	−150.2 (3)
N1—Co1—N2—C14	−83.8 (2)	N3—N4—C14—N2	33.6 (4)
N6—Co1—N2—C25	21.5 (2)	C25—N2—C14—N4	75.6 (4)
N3—Co1—N2—C25	−88.8 (2)	C20—N2—C14—N4	−154.8 (3)
N1—Co1—N2—C25	156.4 (3)	Co1—N2—C14—N4	−41.2 (3)
N6—Co1—N2—C20	−100.6 (2)	N3—N4—C16—C22	−0.4 (4)
N3—Co1—N2—C20	149.2 (2)	C14—N4—C16—C22	−176.8 (3)
N1—Co1—N2—C20	34.4 (2)	N3—N4—C16—C34	178.4 (3)
O1—Co1—N3—C30	−22.3 (4)	C14—N4—C16—C34	1.9 (6)
N6—Co1—N3—C30	90.7 (4)	N5—N6—C17—C12	−0.4 (4)
N1—Co1—N3—C30	−131.3 (4)	Co1—N6—C17—C12	−167.9 (3)
N2—Co1—N3—C30	161.7 (4)	N5—N6—C17—C29	180.0 (3)
O1—Co1—N3—N4	161.1 (2)	Co1—N6—C17—C29	12.5 (6)
N6—Co1—N3—N4	−85.9 (2)	C11—C12—C17—N6	−0.1 (5)
N1—Co1—N3—N4	52.1 (2)	C11—C12—C17—C29	179.5 (4)
N2—Co1—N3—N4	−14.9 (2)	C27—N1—C19—C23	2.2 (5)
O1—Co1—N1—C19	165.4 (3)	Co1—N1—C19—C23	−173.4 (3)
N6—Co1—N1—C19	35.6 (3)	C27—N1—C19—C20	−178.0 (3)
N3—Co1—N1—C19	−91.2 (3)	Co1—N1—C19—C20	6.4 (4)
N2—Co1—N1—C19	−23.1 (3)	C14—N2—C20—C19	72.0 (4)
O1—Co1—N1—C27	−10.0 (3)	C25—N2—C20—C19	−159.6 (3)
N6—Co1—N1—C27	−139.8 (3)	Co1—N2—C20—C19	−41.8 (3)
N3—Co1—N1—C27	93.4 (3)	N1—C19—C20—N2	26.5 (5)
N2—Co1—N1—C27	161.5 (3)	C23—C19—C20—N2	−153.7 (3)
C30—N3—N4—C16	0.6 (4)	N4—C16—C22—C30	0.0 (4)
Co1—N3—N4—C16	178.2 (2)	C34—C16—C22—C30	−178.5 (4)
C30—N3—N4—C14	177.5 (3)	N1—C19—C23—C33	−1.4 (6)
Co1—N3—N4—C14	−4.9 (4)	C20—C19—C23—C33	178.8 (4)
Co1—O1—C8—O2	−0.3 (4)	C11—N5—C25—N2	−154.8 (3)
Co1—O1—C8—C31	−178.0 (3)	N6—N5—C25—N2	39.0 (4)
O1—Co1—N6—C17	−20.9 (4)	C14—N2—C25—N5	−151.6 (3)
N3—Co1—N6—C17	−124.8 (4)	C20—N2—C25—N5	80.1 (4)
N1—Co1—N6—C17	107.2 (4)	Co1—N2—C25—N5	−36.1 (3)
N2—Co1—N6—C17	164.7 (4)	C19—N1—C27—C18	−1.1 (6)
O1—Co1—N6—N5	172.6 (2)	Co1—N1—C27—C18	174.3 (3)
N3—Co1—N6—N5	68.7 (3)	C33—C18—C27—N1	−0.8 (6)
N1—Co1—N6—N5	−59.3 (3)	N4—N3—C30—C22	−0.6 (4)
N2—Co1—N6—N5	−1.8 (2)	Co1—N3—C30—C22	−177.4 (3)
C17—N6—N5—C11	0.7 (4)	N4—N3—C30—C24	177.6 (3)
Co1—N6—N5—C11	171.5 (2)	Co1—N3—C30—C24	0.8 (6)
C17—N6—N5—C25	169.2 (3)	C16—C22—C30—N3	0.4 (4)
Co1—N6—N5—C25	−20.0 (4)	C16—C22—C30—C24	−177.7 (4)
N6—N5—C11—C12	−0.8 (4)	C27—C18—C33—C23	1.6 (7)
C25—N5—C11—C12	−167.8 (4)	C19—C23—C33—C18	−0.6 (6)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···F2	0.97	2.52	3.309 (5)	139
C14—H14A···F3	0.97	2.45	3.234 (5)	138
C22—H22A···F6i	0.93	2.47	3.403 (6)	175
C24—H24C···O2ii	0.96	2.59	3.501 (5)	159
C25—H25A···F4iii	0.97	2.44	3.288 (5)	146
C32—H32C···O2iv	0.96	2.57	3.300 (5)	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14A⋯F2	0.97	2.52	3.309 (5)	139
C14—H14A⋯F3	0.97	2.45	3.234 (5)	138
C22—H22A⋯F6i	0.93	2.47	3.403 (6)	175
C24—H24C⋯O2ii	0.96	2.59	3.501 (5)	159
C25—H25A⋯F4iii	0.97	2.44	3.288 (5)	146
C32—H32C⋯O2iv	0.96	2.57	3.300 (5)	133

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