{Bis[5-methyl-3-(trifluoro-meth-yl)pyrazol-1-yl]borato}{tris-[5-methyl-3-(trifluoro-meth-yl)pyrazol-1-yl]borato}cobalt(II): a structure containing a B-H⋯Co agostic inter-action.

The title compound, [Co(C(10)H(10)BF(6)N(4))(C(15)H(13)BF(9)N(6))], is a neutral Co(II) complex which contains one each of the anionic ligands, bis-(3-trifluoro-methyl-5-methyl-pyrazol-1-yl)borate (Bp) and tris-(3-trifluoro-methyl-5-methyl-pyrazol-1-yl)borate (Tp). A distorted octa-hedral coordination geometry results from ligation of an H atom, which is part of an agostic B-H⋯Co inter-action (H⋯Co = 2.17 Å), and by five imine N atoms, two from a Bp ligand and three from a Tp ligand. In the crystal, mol-ecules form layers parallel to the (10) planes, and the layers are linked along the a axis by C-H⋯F hydrogen bonds. An intra-molecular C-H⋯F inter-action also occurs.

Related literature

For our study of nitro­gen-containing heterocyles, such as expanded-ring imidazoles, and their complexes with metal ions, see: Stibrany & Potenza (2009a ▶). For metal complexes with pyrazole, see: Stibrany & Potenza (2006 ▶, 2009b ▶); Stibrany et al. (1999 ▶, 2005 ▶, 2006 ▶). Copper and cobalt complexes utlizing the title ligand have been prepared for oxidation studies, see: Gorun et al. (2000 ▶). For agostic inter­actions, see: Ruman et al. (2001 ▶, 2002 ▶); Siemer et al. (2001 ▶); Ghosh et al. (1998 ▶).

Experimental

Crystal data

[Co(C10H10BF6N4)(C15H13BF9N6)]

M = 829.08

Monoclinic,

a = 10.8195 (16) Å

b = 16.559 (2) Å

c = 18.687 (3) Å

β = 98.408 (3)°

V = 3312.0 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.64 mm−1

T = 100 K

0.37 × 0.30 × 0.14 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Blessing, 1995 ▶) T min = 0.919, T max = 1.00

33535 measured reflections

7286 independent reflections

6292 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.108

S = 1.00

7286 reflections

495 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.69 e Å−3

Δρmin = −0.44 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT-Plus (Bruker, 2000 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶) and ORTEP-32 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810011773/fk2015sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810011773/fk2015Isup2.hkl

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

[Co(C10H10BF6N4)(C15H13BF9N6)]	F(000) = 1660
Mr = 829.08	Dx = 1.663 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 952 reflections
a = 10.8195 (16) Å	θ = 2.6–26.7°
b = 16.559 (2) Å	µ = 0.64 mm−1
c = 18.687 (3) Å	T = 100 K
β = 98.408 (3)°	Block, orange-red
V = 3312.0 (8) Å3	0.37 × 0.30 × 0.14 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	7286 independent reflections
Radiation source: fine-focus sealed tube	6292 reflections with I > 2σ(I)
graphite	Rint = 0.024
φ and ω scans	θmax = 27.1°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Blessing, 1995)	h = −13→13
Tmin = 0.919, Tmax = 1.00	k = −21→20
33535 measured reflections	l = −23→23

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0612P)2 + 2.660P] where P = (Fo2 + 2Fc2)/3
7286 reflections	(Δ/σ)max = 0.002
495 parameters	Δρmax = 0.69 e Å−3
0 restraints	Δρmin = −0.44 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.67692 (2)	0.302118 (14)	0.620671 (13)	0.01918 (8)
F1	1.04898 (14)	0.32294 (9)	0.81839 (7)	0.0442 (4)
F2	0.97407 (14)	0.41514 (8)	0.74488 (7)	0.0416 (3)
F3	0.85041 (13)	0.33420 (10)	0.78867 (8)	0.0435 (3)
F4	0.81154 (15)	0.11513 (9)	0.37998 (8)	0.0467 (4)
F5	0.97767 (14)	0.18564 (11)	0.40862 (8)	0.0523 (4)
F6	0.85028 (15)	0.21414 (10)	0.31233 (7)	0.0482 (4)
F7	0.54586 (13)	0.19079 (9)	0.75728 (8)	0.0438 (3)
F8	0.44043 (15)	0.08179 (9)	0.73202 (10)	0.0535 (4)
F9	0.38739 (12)	0.19101 (9)	0.67404 (9)	0.0455 (4)
F10	0.99728 (15)	0.51996 (12)	0.60742 (11)	0.0658 (5)
F11	0.86413 (16)	0.50824 (13)	0.51206 (10)	0.0670 (5)
F12	0.93241 (13)	0.40309 (9)	0.56911 (9)	0.0451 (4)
F13	0.44364 (19)	0.19865 (10)	0.50002 (10)	0.0662 (5)
F14	0.25362 (17)	0.23531 (14)	0.47103 (13)	0.0826 (7)
F15	0.4003 (2)	0.29983 (10)	0.43341 (10)	0.0603 (5)
N1	0.86727 (15)	0.26325 (9)	0.65305 (8)	0.0205 (3)
N2	0.90879 (15)	0.20741 (9)	0.60846 (9)	0.0220 (3)
N3	0.70332 (16)	0.29844 (10)	0.51241 (9)	0.0234 (3)
N4	0.77009 (16)	0.23567 (10)	0.49095 (9)	0.0248 (3)
N5	0.64502 (15)	0.17499 (10)	0.62351 (9)	0.0241 (3)
N6	0.70838 (16)	0.13117 (10)	0.57879 (9)	0.0253 (3)
N7	0.72691 (15)	0.42384 (10)	0.64107 (9)	0.0228 (3)
N8	0.65158 (16)	0.45466 (10)	0.68672 (9)	0.0265 (4)
N9	0.48358 (16)	0.32725 (11)	0.60129 (10)	0.0277 (4)
N10	0.45355 (16)	0.37470 (11)	0.65569 (10)	0.0306 (4)
C1	0.95858 (19)	0.33758 (13)	0.76308 (11)	0.0268 (4)
C2	0.96620 (18)	0.28046 (11)	0.70255 (10)	0.0218 (4)
C3	1.07128 (18)	0.23733 (12)	0.69001 (11)	0.0256 (4)
H3	1.1527	0.2394	0.7170	0.031*
C4	1.03149 (19)	0.19085 (12)	0.62981 (11)	0.0266 (4)
C5	1.1019 (2)	0.12976 (16)	0.59297 (14)	0.0402 (6)
H5A	1.0657	0.0761	0.5978	0.060*
H5B	1.1897	0.1296	0.6153	0.060*
H5C	1.0965	0.1435	0.5416	0.060*
C6	0.8573 (2)	0.19030 (15)	0.38120 (12)	0.0370 (5)
C7	0.7869 (2)	0.24756 (14)	0.42153 (11)	0.0297 (4)
C8	0.7303 (2)	0.31839 (14)	0.39755 (11)	0.0320 (5)
H8	0.7273	0.3419	0.3510	0.038*
C9	0.67811 (19)	0.34874 (12)	0.45617 (11)	0.0267 (4)
C10	0.6041 (2)	0.42469 (13)	0.45943 (12)	0.0321 (5)
H10A	0.5714	0.4271	0.5056	0.048*
H10B	0.5344	0.4252	0.4195	0.048*
H10C	0.6580	0.4715	0.4553	0.048*
C11	0.4863 (2)	0.14675 (14)	0.70263 (13)	0.0349 (5)
C12	0.56841 (19)	0.12256 (13)	0.64936 (12)	0.0294 (4)
C13	0.5808 (2)	0.04605 (13)	0.62153 (14)	0.0385 (5)
H13	0.5364	−0.0013	0.6311	0.046*
C14	0.6711 (2)	0.05289 (13)	0.57699 (13)	0.0350 (5)
C15	0.7250 (3)	−0.01038 (15)	0.53330 (17)	0.0528 (7)
H15A	0.7172	0.0071	0.4827	0.079*
H15B	0.6797	−0.0613	0.5362	0.079*
H15C	0.8134	−0.0184	0.5524	0.079*
C16	0.8966 (2)	0.47835 (14)	0.57809 (13)	0.0349 (5)
C17	0.79552 (19)	0.48610 (12)	0.62379 (12)	0.0281 (4)
C18	0.7643 (2)	0.55635 (13)	0.65694 (14)	0.0392 (6)
H18	0.7989	0.6086	0.6530	0.047*
C19	0.6729 (2)	0.53452 (14)	0.69650 (13)	0.0362 (5)
C20	0.6035 (3)	0.58409 (19)	0.74419 (18)	0.0596 (9)
H20A	0.5154	0.5876	0.7228	0.089*
H20B	0.6395	0.6385	0.7491	0.089*
H20C	0.6100	0.5587	0.7920	0.089*
C21	0.3685 (2)	0.26228 (14)	0.49148 (15)	0.0430 (6)
C22	0.3755 (2)	0.31429 (13)	0.55705 (14)	0.0347 (5)
C23	0.2776 (2)	0.35359 (15)	0.58241 (15)	0.0414 (6)
H23	0.1924	0.3542	0.5611	0.050*
C24	0.3302 (2)	0.39173 (15)	0.64533 (14)	0.0392 (6)
C25	0.2719 (3)	0.44475 (19)	0.69549 (16)	0.0544 (8)
H25A	0.2817	0.4201	0.7437	0.082*
H25B	0.1829	0.4514	0.6773	0.082*
H25C	0.3129	0.4977	0.6985	0.082*
B1	0.8187 (2)	0.16910 (14)	0.54601 (12)	0.0250 (4)
B2	0.5641 (3)	0.39322 (17)	0.71633 (14)	0.0342 (5)
H1B	0.865 (2)	0.1208 (14)	0.5190 (12)	0.021 (5)*
H21B	0.537 (2)	0.4097 (16)	0.7632 (14)	0.039 (7)*
H22B	0.623 (2)	0.3326 (16)	0.7245 (13)	0.034 (6)*

	U11	U22	U33	U12	U13	U23
Co1	0.01869 (13)	0.01639 (13)	0.02269 (14)	0.00083 (9)	0.00378 (9)	0.00099 (9)
F1	0.0457 (8)	0.0479 (8)	0.0336 (7)	0.0131 (7)	−0.0119 (6)	−0.0087 (6)
F2	0.0560 (9)	0.0245 (6)	0.0418 (8)	−0.0014 (6)	−0.0008 (6)	−0.0054 (5)
F3	0.0374 (7)	0.0564 (9)	0.0388 (7)	−0.0033 (7)	0.0125 (6)	−0.0156 (7)
F4	0.0610 (10)	0.0411 (8)	0.0383 (8)	0.0064 (7)	0.0084 (7)	−0.0108 (6)
F5	0.0371 (8)	0.0768 (12)	0.0437 (8)	0.0101 (7)	0.0081 (6)	−0.0089 (8)
F6	0.0538 (9)	0.0634 (10)	0.0296 (7)	0.0059 (8)	0.0139 (6)	−0.0045 (6)
F7	0.0353 (7)	0.0552 (9)	0.0426 (8)	0.0054 (6)	0.0120 (6)	0.0043 (7)
F8	0.0480 (9)	0.0410 (8)	0.0773 (11)	0.0004 (7)	0.0284 (8)	0.0288 (8)
F9	0.0249 (7)	0.0527 (9)	0.0593 (9)	0.0102 (6)	0.0081 (6)	0.0264 (7)
F10	0.0372 (8)	0.0734 (12)	0.0866 (13)	−0.0277 (8)	0.0084 (8)	−0.0085 (10)
F11	0.0490 (9)	0.0924 (14)	0.0610 (10)	0.0132 (9)	0.0128 (8)	0.0483 (10)
F12	0.0412 (8)	0.0387 (8)	0.0615 (9)	0.0026 (6)	0.0275 (7)	0.0110 (7)
F13	0.0834 (13)	0.0372 (8)	0.0654 (11)	0.0137 (8)	−0.0310 (10)	−0.0072 (7)
F14	0.0451 (10)	0.0953 (16)	0.1006 (16)	−0.0343 (10)	−0.0126 (10)	−0.0172 (13)
F15	0.0841 (13)	0.0401 (9)	0.0539 (10)	−0.0147 (8)	0.0003 (9)	0.0004 (7)
N1	0.0219 (8)	0.0167 (7)	0.0234 (8)	0.0002 (6)	0.0045 (6)	0.0006 (6)
N2	0.0222 (8)	0.0202 (8)	0.0242 (8)	0.0011 (6)	0.0054 (6)	−0.0018 (6)
N3	0.0248 (8)	0.0203 (8)	0.0248 (8)	−0.0004 (6)	0.0021 (6)	−0.0006 (6)
N4	0.0255 (8)	0.0244 (8)	0.0243 (8)	−0.0003 (7)	0.0032 (6)	−0.0037 (6)
N5	0.0205 (8)	0.0211 (8)	0.0304 (8)	−0.0010 (6)	0.0027 (6)	0.0038 (6)
N6	0.0271 (8)	0.0178 (8)	0.0304 (8)	−0.0009 (6)	0.0019 (7)	−0.0011 (6)
N7	0.0228 (8)	0.0212 (8)	0.0244 (8)	0.0026 (6)	0.0038 (6)	−0.0006 (6)
N8	0.0271 (8)	0.0262 (8)	0.0253 (8)	0.0080 (7)	0.0011 (7)	−0.0070 (7)
N9	0.0216 (8)	0.0248 (8)	0.0369 (9)	−0.0010 (7)	0.0047 (7)	0.0060 (7)
N10	0.0249 (9)	0.0298 (9)	0.0402 (10)	0.0044 (7)	0.0147 (7)	0.0106 (8)
C1	0.0252 (10)	0.0261 (10)	0.0279 (10)	0.0021 (8)	−0.0003 (8)	−0.0008 (8)
C2	0.0224 (9)	0.0191 (8)	0.0238 (9)	−0.0027 (7)	0.0031 (7)	0.0037 (7)
C3	0.0198 (9)	0.0264 (10)	0.0307 (10)	−0.0013 (7)	0.0037 (7)	0.0025 (8)
C4	0.0221 (9)	0.0284 (10)	0.0302 (10)	0.0025 (8)	0.0069 (8)	0.0017 (8)
C5	0.0276 (11)	0.0487 (14)	0.0445 (13)	0.0109 (10)	0.0055 (10)	−0.0130 (11)
C6	0.0374 (12)	0.0458 (14)	0.0283 (11)	0.0024 (10)	0.0067 (9)	−0.0042 (9)
C7	0.0298 (10)	0.0347 (11)	0.0242 (9)	−0.0041 (8)	0.0028 (8)	−0.0039 (8)
C8	0.0362 (12)	0.0354 (12)	0.0240 (10)	−0.0036 (9)	0.0031 (8)	0.0014 (8)
C9	0.0279 (10)	0.0262 (10)	0.0245 (9)	−0.0050 (8)	−0.0013 (8)	0.0011 (8)
C10	0.0399 (12)	0.0243 (10)	0.0305 (10)	0.0009 (9)	−0.0002 (9)	0.0055 (8)
C11	0.0245 (10)	0.0343 (12)	0.0464 (13)	0.0023 (9)	0.0069 (9)	0.0194 (10)
C12	0.0230 (10)	0.0262 (10)	0.0376 (11)	−0.0021 (8)	−0.0001 (8)	0.0115 (8)
C13	0.0376 (12)	0.0232 (10)	0.0530 (14)	−0.0079 (9)	0.0008 (11)	0.0074 (10)
C14	0.0378 (12)	0.0211 (10)	0.0443 (12)	−0.0057 (9)	0.0002 (10)	0.0005 (9)
C15	0.0657 (18)	0.0217 (11)	0.0725 (19)	−0.0089 (11)	0.0149 (15)	−0.0126 (12)
C16	0.0261 (10)	0.0325 (11)	0.0448 (13)	−0.0050 (9)	0.0008 (9)	0.0137 (10)
C17	0.0236 (9)	0.0210 (9)	0.0368 (11)	−0.0007 (7)	−0.0051 (8)	0.0030 (8)
C18	0.0309 (11)	0.0203 (10)	0.0602 (15)	−0.0005 (8)	−0.0143 (10)	−0.0047 (10)
C19	0.0305 (11)	0.0283 (11)	0.0445 (13)	0.0090 (9)	−0.0122 (9)	−0.0152 (9)
C20	0.0492 (16)	0.0520 (17)	0.0720 (19)	0.0197 (13)	−0.0102 (14)	−0.0396 (15)
C21	0.0359 (12)	0.0273 (11)	0.0590 (15)	−0.0096 (9)	−0.0161 (11)	0.0102 (11)
C22	0.0231 (10)	0.0267 (11)	0.0525 (14)	−0.0043 (8)	−0.0007 (9)	0.0164 (9)
C23	0.0195 (10)	0.0385 (13)	0.0656 (16)	0.0001 (9)	0.0042 (10)	0.0263 (12)
C24	0.0259 (11)	0.0386 (12)	0.0566 (15)	0.0087 (9)	0.0182 (10)	0.0266 (11)
C25	0.0419 (14)	0.0625 (18)	0.0663 (18)	0.0238 (13)	0.0327 (13)	0.0268 (15)
B1	0.0253 (11)	0.0230 (10)	0.0264 (11)	0.0009 (8)	0.0028 (9)	−0.0028 (8)
B2	0.0352 (13)	0.0410 (14)	0.0286 (12)	0.0114 (11)	0.0118 (10)	0.0064 (10)

Co1—N3	2.0850 (17)	C2—C3	1.391 (3)
Co1—N7	2.1072 (17)	C3—C4	1.379 (3)
Co1—N9	2.1115 (18)	C3—H3	0.9500
Co1—N5	2.1351 (17)	C4—C5	1.493 (3)
Co1—N1	2.1581 (16)	C5—H5A	0.9800
Co1—H22B	2.17 (2)	C5—H5B	0.9800
F1—C1	1.337 (2)	C5—H5C	0.9800
F2—C1	1.345 (2)	C6—C7	1.489 (3)
F3—C1	1.329 (2)	C7—C8	1.368 (3)
F4—C6	1.339 (3)	C8—C9	1.397 (3)
F5—C6	1.330 (3)	C8—H8	0.9500
F6—C6	1.338 (3)	C9—C10	1.497 (3)
F7—C11	1.341 (3)	C10—H10A	0.9800
F8—C11	1.336 (2)	C10—H10B	0.9800
F9—C11	1.342 (2)	C10—H10C	0.9800
F10—C16	1.337 (3)	C11—C12	1.483 (3)
F11—C16	1.328 (3)	C12—C13	1.384 (3)
F12—C16	1.323 (3)	C13—C14	1.377 (3)
F13—C21	1.326 (3)	C13—H13	0.9500
F14—C21	1.323 (3)	C14—C15	1.498 (3)
F15—C21	1.339 (3)	C15—H15A	0.9800
N1—C2	1.339 (2)	C15—H15B	0.9800
N1—N2	1.364 (2)	C15—H15C	0.9800
N2—C4	1.357 (3)	C16—C17	1.488 (3)
N2—B1	1.543 (3)	C17—C18	1.383 (3)
N3—C9	1.337 (3)	C18—C19	1.367 (4)
N3—N4	1.359 (2)	C18—H18	0.9500
N4—C7	1.350 (3)	C19—C20	1.493 (3)
N4—B1	1.547 (3)	C20—H20A	0.9800
N5—C12	1.338 (3)	C20—H20B	0.9800
N5—N6	1.365 (2)	C20—H20C	0.9800
N6—C14	1.357 (3)	C21—C22	1.490 (4)
N6—B1	1.551 (3)	C22—C23	1.384 (3)
N7—C17	1.337 (3)	C23—C24	1.382 (4)
N7—N8	1.362 (2)	C23—H23	0.9500
N8—C19	1.350 (3)	C24—C25	1.490 (4)
N8—B2	1.546 (3)	C25—H25A	0.9800
N9—C22	1.347 (3)	C25—H25B	0.9800
N9—N10	1.361 (3)	C25—H25C	0.9800
N10—C24	1.350 (3)	B1—H1B	1.10 (2)
N10—B2	1.554 (3)	B2—H21B	1.00 (3)
C1—C2	1.486 (3)	B2—H22B	1.18 (3)
N3—Co1—N7	97.79 (6)	C9—C10—H10B	109.5
N3—Co1—N9	96.44 (7)	H10A—C10—H10B	109.5
N7—Co1—N9	93.68 (7)	C9—C10—H10C	109.5
N3—Co1—N5	92.34 (6)	H10A—C10—H10C	109.5
N7—Co1—N5	167.62 (6)	H10B—C10—H10C	109.5
N9—Co1—N5	92.23 (7)	F8—C11—F7	106.91 (19)
N3—Co1—N1	90.16 (6)	F8—C11—F9	106.34 (17)
N7—Co1—N1	91.45 (6)	F7—C11—F9	105.8 (2)
N9—Co1—N1	171.01 (6)	F8—C11—C12	110.7 (2)
N5—Co1—N1	81.38 (6)	F7—C11—C12	112.91 (18)
N3—Co1—H22B	165.7 (7)	F9—C11—C12	113.67 (19)
N7—Co1—H22B	73.2 (7)	N5—C12—C13	111.1 (2)
N9—Co1—H22B	73.5 (7)	N5—C12—C11	122.0 (2)
N5—Co1—H22B	98.1 (7)	C13—C12—C11	126.9 (2)
N1—Co1—H22B	101.0 (7)	C14—C13—C12	105.54 (19)
C2—N1—N2	105.35 (15)	C14—C13—H13	127.2
C2—N1—Co1	139.81 (13)	C12—C13—H13	127.2
N2—N1—Co1	114.64 (12)	N6—C14—C13	107.4 (2)
C4—N2—N1	110.66 (16)	N6—C14—C15	122.9 (2)
C4—N2—B1	128.46 (16)	C13—C14—C15	129.7 (2)
N1—N2—B1	120.82 (15)	C14—C15—H15A	109.5
C9—N3—N4	107.49 (16)	C14—C15—H15B	109.5
C9—N3—Co1	134.68 (14)	H15A—C15—H15B	109.5
N4—N3—Co1	117.56 (12)	C14—C15—H15C	109.5
C7—N4—N3	108.89 (17)	H15A—C15—H15C	109.5
C7—N4—B1	131.52 (17)	H15B—C15—H15C	109.5
N3—N4—B1	119.49 (16)	F12—C16—F11	106.0 (2)
C12—N5—N6	105.62 (16)	F12—C16—F10	107.54 (19)
C12—N5—Co1	139.42 (15)	F11—C16—F10	106.13 (19)
N6—N5—Co1	114.30 (12)	F12—C16—C17	114.03 (17)
C14—N6—N5	110.41 (17)	F11—C16—C17	112.59 (19)
C14—N6—B1	128.35 (18)	F10—C16—C17	110.1 (2)
N5—N6—B1	120.71 (16)	N7—C17—C18	111.1 (2)
C17—N7—N8	105.45 (16)	N7—C17—C16	123.54 (19)
C17—N7—Co1	146.16 (14)	C18—C17—C16	125.3 (2)
N8—N7—Co1	108.08 (12)	C19—C18—C17	105.3 (2)
C19—N8—N7	110.21 (18)	C19—C18—H18	127.4
C19—N8—B2	134.25 (19)	C17—C18—H18	127.4
N7—N8—B2	115.54 (16)	N8—C19—C18	107.99 (19)
C22—N9—N10	105.65 (18)	N8—C19—C20	121.9 (3)
C22—N9—Co1	145.42 (17)	C18—C19—C20	130.1 (2)
N10—N9—Co1	108.92 (13)	C19—C20—H20A	109.5
C24—N10—N9	110.6 (2)	C19—C20—H20B	109.5
C24—N10—B2	134.7 (2)	H20A—C20—H20B	109.5
N9—N10—B2	114.60 (16)	C19—C20—H20C	109.5
F3—C1—F1	107.30 (17)	H20A—C20—H20C	109.5
F3—C1—F2	106.26 (17)	H20B—C20—H20C	109.5
F1—C1—F2	105.33 (17)	F14—C21—F13	107.5 (2)
F3—C1—C2	113.39 (17)	F14—C21—F15	105.4 (2)
F1—C1—C2	110.93 (17)	F13—C21—F15	103.9 (2)
F2—C1—C2	113.11 (17)	F14—C21—C22	111.4 (2)
N1—C2—C3	111.40 (17)	F13—C21—C22	113.8 (2)
N1—C2—C1	122.25 (17)	F15—C21—C22	114.20 (19)
C3—C2—C1	126.34 (18)	N9—C22—C23	110.7 (2)
C4—C3—C2	104.99 (18)	N9—C22—C21	122.1 (2)
C4—C3—H3	127.5	C23—C22—C21	127.1 (2)
C2—C3—H3	127.5	C24—C23—C22	105.4 (2)
N2—C4—C3	107.60 (17)	C24—C23—H23	127.3
N2—C4—C5	122.97 (19)	C22—C23—H23	127.3
C3—C4—C5	129.40 (19)	N10—C24—C23	107.6 (2)
C4—C5—H5A	109.5	N10—C24—C25	122.2 (3)
C4—C5—H5B	109.5	C23—C24—C25	130.2 (2)
H5A—C5—H5B	109.5	C24—C25—H25A	109.5
C4—C5—H5C	109.5	C24—C25—H25B	109.5
H5A—C5—H5C	109.5	H25A—C25—H25B	109.5
H5B—C5—H5C	109.5	C24—C25—H25C	109.5
F5—C6—F6	107.6 (2)	H25A—C25—H25C	109.5
F5—C6—F4	106.9 (2)	H25B—C25—H25C	109.5
F6—C6—F4	106.81 (19)	N2—B1—N4	109.02 (16)
F5—C6—C7	112.75 (19)	N2—B1—N6	107.77 (16)
F6—C6—C7	109.7 (2)	N4—B1—N6	110.19 (16)
F4—C6—C7	112.67 (19)	N2—B1—H1B	111.4 (12)
N4—C7—C8	108.87 (19)	N4—B1—H1B	110.1 (11)
N4—C7—C6	123.0 (2)	N6—B1—H1B	108.3 (12)
C8—C7—C6	128.2 (2)	N8—B2—N10	108.37 (17)
C7—C8—C9	105.33 (19)	N8—B2—H21B	113.9 (16)
C7—C8—H8	127.3	N10—B2—H21B	113.7 (15)
C9—C8—H8	127.3	N8—B2—H22B	105.1 (12)
N3—C9—C8	109.43 (19)	N10—B2—H22B	105.5 (12)
N3—C9—C10	122.69 (18)	H21B—B2—H22B	109.6 (19)
C8—C9—C10	127.88 (19)	B2—H22B—Co1	107 (1)
C9—C10—H10A	109.5
N3—Co1—N1—C2	136.1 (2)	N3—N4—C7—C6	179.51 (19)
N7—Co1—N1—C2	38.3 (2)	B1—N4—C7—C6	3.4 (3)
N5—Co1—N1—C2	−131.5 (2)	F5—C6—C7—N4	−65.0 (3)
H22B—Co1—N1—C2	−34.9 (7)	F6—C6—C7—N4	175.1 (2)
N3—Co1—N1—N2	−37.84 (12)	F4—C6—C7—N4	56.2 (3)
N7—Co1—N1—N2	−135.64 (12)	F5—C6—C7—C8	114.7 (3)
N5—Co1—N1—N2	54.51 (12)	F6—C6—C7—C8	−5.3 (3)
H22B—Co1—N1—N2	151.2 (7)	F4—C6—C7—C8	−124.1 (2)
C2—N1—N2—C4	−0.4 (2)	N4—C7—C8—C9	−0.1 (2)
Co1—N1—N2—C4	175.57 (12)	C6—C7—C8—C9	−179.8 (2)
C2—N1—N2—B1	176.91 (16)	N4—N3—C9—C8	−0.5 (2)
Co1—N1—N2—B1	−7.1 (2)	Co1—N3—C9—C8	173.09 (15)
N7—Co1—N3—C9	−41.0 (2)	N4—N3—C9—C10	179.22 (18)
N9—Co1—N3—C9	53.6 (2)	Co1—N3—C9—C10	−7.2 (3)
N5—Co1—N3—C9	146.09 (19)	C7—C8—C9—N3	0.4 (2)
N1—Co1—N3—C9	−132.53 (19)	C7—C8—C9—C10	−179.3 (2)
H22B—Co1—N3—C9	9(3)	N6—N5—C12—C13	−0.5 (2)
N7—Co1—N3—N4	132.08 (13)	Co1—N5—C12—C13	168.92 (17)
N9—Co1—N3—N4	−133.29 (13)	N6—N5—C12—C11	177.70 (18)
N5—Co1—N3—N4	−40.79 (14)	Co1—N5—C12—C11	−12.9 (3)
N1—Co1—N3—N4	40.59 (14)	F8—C11—C12—N5	−166.19 (19)
H22B—Co1—N3—N4	−178 (3)	F7—C11—C12—N5	−46.4 (3)
C9—N3—N4—C7	0.4 (2)	F9—C11—C12—N5	74.2 (3)
Co1—N3—N4—C7	−174.44 (13)	F8—C11—C12—C13	11.7 (3)
C9—N3—N4—B1	177.10 (17)	F7—C11—C12—C13	131.5 (2)
Co1—N3—N4—B1	2.2 (2)	F9—C11—C12—C13	−107.9 (3)
N3—Co1—N5—C12	−137.6 (2)	N5—C12—C13—C14	0.7 (3)
N7—Co1—N5—C12	77.4 (4)	C11—C12—C13—C14	−177.4 (2)
N9—Co1—N5—C12	−41.1 (2)	N5—N6—C14—C13	0.2 (2)
N1—Co1—N5—C12	132.6 (2)	B1—N6—C14—C13	171.8 (2)
H22B—Co1—N5—C12	32.6 (7)	N5—N6—C14—C15	−179.2 (2)
N3—Co1—N5—N6	31.20 (13)	B1—N6—C14—C15	−7.6 (4)
N7—Co1—N5—N6	−113.8 (3)	C12—C13—C14—N6	−0.5 (3)
N9—Co1—N5—N6	127.74 (13)	C12—C13—C14—C15	178.9 (3)
N1—Co1—N5—N6	−58.61 (13)	N8—N7—C17—C18	−0.7 (2)
H22B—Co1—N5—N6	−158.6 (7)	Co1—N7—C17—C18	171.47 (18)
C12—N5—N6—C14	0.2 (2)	N8—N7—C17—C16	176.13 (18)
Co1—N5—N6—C14	−172.32 (14)	Co1—N7—C17—C16	−11.7 (4)
C12—N5—N6—B1	−172.15 (17)	F12—C16—C17—N7	−14.3 (3)
Co1—N5—N6—B1	15.4 (2)	F11—C16—C17—N7	106.5 (2)
N3—Co1—N7—C17	−28.7 (2)	F10—C16—C17—N7	−135.3 (2)
N9—Co1—N7—C17	−125.7 (2)	F12—C16—C17—C18	162.0 (2)
N5—Co1—N7—C17	116.0 (3)	F11—C16—C17—C18	−77.1 (3)
N1—Co1—N7—C17	61.7 (2)	F10—C16—C17—C18	41.1 (3)
H22B—Co1—N7—C17	162.7 (7)	N7—C17—C18—C19	0.5 (3)
N3—Co1—N7—N8	143.38 (12)	C16—C17—C18—C19	−176.3 (2)
N9—Co1—N7—N8	46.36 (12)	N7—N8—C19—C18	−0.3 (2)
N5—Co1—N7—N8	−72.0 (3)	B2—N8—C19—C18	178.6 (2)
N1—Co1—N7—N8	−126.26 (12)	N7—N8—C19—C20	−179.9 (2)
H22B—Co1—N7—N8	−25.2 (7)	B2—N8—C19—C20	−0.9 (4)
C17—N7—N8—C19	0.6 (2)	C17—C18—C19—N8	−0.1 (2)
Co1—N7—N8—C19	−174.78 (13)	C17—C18—C19—C20	179.4 (2)
C17—N7—N8—B2	−178.54 (17)	N10—N9—C22—C23	0.6 (2)
Co1—N7—N8—B2	6.0 (2)	Co1—N9—C22—C23	178.91 (19)
N3—Co1—N9—C22	34.9 (3)	N10—N9—C22—C21	−178.06 (19)
N7—Co1—N9—C22	133.2 (3)	Co1—N9—C22—C21	0.3 (4)
N5—Co1—N9—C22	−57.7 (3)	F14—C21—C22—N9	158.1 (2)
H22B—Co1—N9—C22	−155.5 (8)	F13—C21—C22—N9	36.4 (3)
N3—Co1—N9—N10	−146.81 (12)	F15—C21—C22—N9	−82.7 (3)
N7—Co1—N9—N10	−48.53 (13)	F14—C21—C22—C23	−20.3 (3)
N5—Co1—N9—N10	120.58 (13)	F13—C21—C22—C23	−142.0 (2)
H22B—Co1—N9—N10	22.8 (7)	F15—C21—C22—C23	98.9 (3)
C22—N9—N10—C24	−0.7 (2)	N9—C22—C23—C24	−0.3 (2)
Co1—N9—N10—C24	−179.68 (13)	C21—C22—C23—C24	178.3 (2)
C22—N9—N10—B2	176.42 (17)	N9—N10—C24—C23	0.5 (2)
Co1—N9—N10—B2	−2.6 (2)	B2—N10—C24—C23	−175.8 (2)
N2—N1—C2—C3	0.8 (2)	N9—N10—C24—C25	−178.1 (2)
Co1—N1—C2—C3	−173.55 (14)	B2—N10—C24—C25	5.6 (4)
N2—N1—C2—C1	−177.99 (17)	C22—C23—C24—N10	−0.2 (2)
Co1—N1—C2—C1	7.7 (3)	C22—C23—C24—C25	178.3 (2)
F3—C1—C2—N1	35.8 (3)	C4—N2—B1—N4	−119.1 (2)
F1—C1—C2—N1	156.65 (18)	N1—N2—B1—N4	64.2 (2)
F2—C1—C2—N1	−85.3 (2)	C4—N2—B1—N6	121.4 (2)
F3—C1—C2—C3	−142.7 (2)	N1—N2—B1—N6	−55.4 (2)
F1—C1—C2—C3	−21.9 (3)	C7—N4—B1—N2	114.3 (2)
F2—C1—C2—C3	96.2 (2)	N3—N4—B1—N2	−61.4 (2)
N1—C2—C3—C4	−0.8 (2)	C7—N4—B1—N6	−127.6 (2)
C1—C2—C3—C4	177.86 (19)	N3—N4—B1—N6	56.6 (2)
N1—N2—C4—C3	−0.1 (2)	C14—N6—B1—N2	−120.1 (2)
B1—N2—C4—C3	−177.15 (18)	N5—N6—B1—N2	50.7 (2)
N1—N2—C4—C5	177.78 (19)	C14—N6—B1—N4	121.0 (2)
B1—N2—C4—C5	0.7 (3)	N5—N6—B1—N4	−68.2 (2)
C2—C3—C4—N2	0.6 (2)	C19—N8—B2—N10	104.5 (3)
C2—C3—C4—C5	−177.2 (2)	N7—N8—B2—N10	−76.6 (2)
N3—N4—C7—C8	−0.2 (2)	C24—N10—B2—N8	−110.2 (2)
B1—N4—C7—C8	−176.3 (2)	N9—N10—B2—N8	73.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5B···F9i	0.98	2.48	3.391 (3)	155
C10—H10C···F11	0.98	2.40	3.160 (3)	134
C25—H25B···F10ii	0.98	2.50	3.414 (4)	155

Co1—N3	2.0850 (17)
Co1—N7	2.1072 (17)
Co1—N9	2.1115 (18)
Co1—N5	2.1351 (17)
Co1—N1	2.1581 (16)
Co1—H22B	2.17 (2)
B1—H1B	1.10 (2)
B2—H21B	1.00 (3)
B2—H22B	1.18 (3)

H21B—B2—H22B	109.6 (19)
B2—H22B—Co1	107 (1)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5B⋯F9i	0.98	2.48	3.391 (3)	155
C10—H10C⋯F11	0.98	2.40	3.160 (3)	134
C25—H25B⋯F10ii	0.98	2.50	3.414 (4)	155

Symmetry codes: (i) ; (ii) .