Tetra-ethyl-ammonium (2,2'-bipyridine)tetra-cyanidocobaltate(III) sesquihydrate acetonitrile solvate.

The title complex, (C(8)H(20)N)[Co(CN)(4)(C(10)H(8)N(2))]·CH(3)CN·1.5H(2)O, consists of tetra-ethyl ammonium cations, mononuclear [Co(III)bpy(CN)(4)](-) anions and uncoordinated water and acetonitrile mol-ecules. The Co(III) atom is six-coordinated by two 2,2'-bipyridine (bpy) N atoms and four cyanide C atoms in a distorted octa-hedral geometry. The acute bite angle of the chelating bpy [82.28 (8)°] is the main factor accounting for this distortion. In addition, the tetra-ethyl-ammonium cation is significantly disordered [occupancy ratio 0.611 (3):0.389 (3)]. The presence of water mol-ecules, one of which is disordered over two positions about an inversion center, results in the formation of a network of O-H⋯N hydrogen bonds involving the cyanide N atoms.

Related literature

For the starting complex [Co(bpy)3]Cl2·2H2O·CH3CH2OH, see: Szalda et al. (1983 ▶). For a similar building block with a tetra­phenyl­phospho­nium cation and chromium(III), and a nuclearity controlled cyanide-bridged bimetallic compound, see: Toma et al. (2004 ▶); with a potassium cation and tetra­phenyl­arsonium cation and iron(III), and cyanide-bridged heterobimetallic complexes, see: Toma et al. (2007 ▶); with a tetra­phenyl­phospho­nium cation and iron(III) and ribbon-like ferromagnetic cyano-bridged chains, see: Lescoueezec et al. (2002 ▶). For potential applications of bimetallic clusters as catalysts, see: Darensbourg & Phelps (2004 ▶), as room temperature magnets, see: Mallah et al. (1993 ▶); Garde et al. (2002 ▶); Holmes & Girolami (1999 ▶) and as single-mol­ecule magnets, see: Sokol et al. (2002 ▶). For attempts to make a similar building block with nickel(II), see: Lyubartseva & Parkin (2009 ▶).

Experimental

Crystal data

(C8H20N)[Co(CN)4(C10H8N2)]·C2H3N·1.5H2O

M = 517.52

Monoclinic,

a = 10.1591 (1) Å

b = 23.4015 (3) Å

c = 11.3422 (2) Å

β = 97.3080 (5)°

V = 2674.57 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.68 mm−1

T = 90 K

0.30 × 0.27 × 0.25 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.709, T max = 0.849

28623 measured reflections

4704 independent reflections

3689 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.108

S = 1.05

4704 reflections

378 parameters

60 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.69 e Å−3

Δρmin = −0.33 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO-SMN (Otwinowski & Minor, 1997 ▶); 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: SHELXL97 and local procedures.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810011311/kp2254sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810011311/kp2254Isup2.hkl

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

(C8H20N)[Co(CN)4(C10H8N2)]·C2H3N·1.5H2O	F(000) = 1092
Mr = 517.52	Dx = 1.285 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6273 reflections
a = 10.1591 (1) Å	θ = 1.0–27.5°
b = 23.4015 (3) Å	µ = 0.68 mm−1
c = 11.3422 (2) Å	T = 90 K
β = 97.3080 (5)°	Block, yellow
V = 2674.57 (6) Å3	0.30 × 0.27 × 0.25 mm
Z = 4

Nonius KappaCCD diffractometer	4704 independent reflections
Radiation source: fine-focus sealed tube	3689 reflections with I > 2σ(I)
graphite	Rint = 0.048
Detector resolution: 9.1 pixels mm-1	θmax = 25.0°, θmin = 2.0°
ω scans at fixed χ = 55°	h = −12→12
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	k = −27→27
Tmin = 0.709, Tmax = 0.849	l = −13→13
28623 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0481P)2 + 2.6305P] where P = (Fo2 + 2Fc2)/3
4704 reflections	(Δ/σ)max = 0.001
378 parameters	Δρmax = 0.69 e Å−3
60 restraints	Δρmin = −0.33 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 > 2σ(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)
Co1	0.66787 (3)	0.093308 (13)	0.27408 (3)	0.02317 (12)
N1	0.7419 (2)	0.05486 (8)	0.42108 (19)	0.0238 (5)
N2	0.5597 (2)	0.02349 (8)	0.25393 (18)	0.0240 (5)
C1	0.8401 (3)	0.07455 (11)	0.5019 (2)	0.0292 (6)
H1	0.8782	0.1108	0.4895	0.035*
C2	0.8872 (3)	0.04358 (12)	0.6025 (3)	0.0383 (7)
H2	0.9566	0.0584	0.6582	0.046*
C3	0.8320 (3)	−0.00906 (13)	0.6209 (3)	0.0431 (8)
H3	0.8626	−0.0308	0.6896	0.052*
C4	0.7314 (3)	−0.02991 (12)	0.5380 (2)	0.0350 (7)
H4	0.6926	−0.0661	0.5491	0.042*
C5	0.6881 (3)	0.00296 (10)	0.4384 (2)	0.0254 (6)
C6	0.5839 (3)	−0.01476 (10)	0.3436 (2)	0.0239 (6)
C7	0.5152 (3)	−0.06600 (11)	0.3423 (2)	0.0287 (6)
H7	0.5339	−0.0925	0.4057	0.034*
C8	0.4195 (3)	−0.07813 (11)	0.2483 (2)	0.0320 (6)
H8	0.3712	−0.1129	0.2463	0.038*
C9	0.3946 (3)	−0.03900 (11)	0.1567 (2)	0.0321 (6)
H9	0.3293	−0.0465	0.0909	0.039*
C10	0.4668 (3)	0.01138 (11)	0.1630 (2)	0.0293 (6)
H10	0.4497	0.0383	0.1002	0.035*
N3	0.8813 (3)	0.03848 (11)	0.1447 (3)	0.0600 (9)
C11	0.8014 (3)	0.05929 (11)	0.1935 (3)	0.0350 (7)
N4	0.8354 (2)	0.19977 (9)	0.3179 (2)	0.0337 (5)
C12	0.7721 (3)	0.15893 (11)	0.3010 (2)	0.0263 (6)
N5	0.5526 (3)	0.14664 (10)	0.0403 (2)	0.0375 (6)
C13	0.5958 (3)	0.12650 (11)	0.1303 (2)	0.0293 (6)
N6	0.4571 (2)	0.15090 (9)	0.4029 (2)	0.0281 (5)
C14	0.5359 (2)	0.12964 (10)	0.3530 (2)	0.0224 (5)
N1C	0.1397 (2)	0.17482 (9)	0.03158 (18)	0.0240 (5)
C1C	0.2239 (5)	0.16359 (19)	−0.0684 (4)	0.0317 (11)	0.611 (3)
H1C1	0.1910	0.1883	−0.1368	0.038*	0.611 (3)
H1C2	0.3164	0.1752	−0.0408	0.038*	0.611 (3)
C2C	0.225 (3)	0.1027 (8)	−0.1111 (16)	0.0409 (18)	0.611 (3)
H2C1	0.2810	0.0997	−0.1750	0.061*	0.611 (3)
H2C2	0.1343	0.0909	−0.1410	0.061*	0.611 (3)
H2C3	0.2602	0.0778	−0.0450	0.061*	0.611 (3)
C3C	0.0006 (4)	0.1547 (2)	0.0034 (4)	0.0306 (11)	0.611 (3)
H3C1	−0.0495	0.1659	0.0691	0.037*	0.611 (3)
H3C2	0.0007	0.1124	−0.0005	0.037*	0.611 (3)
C4C	−0.0712 (10)	0.1778 (4)	−0.1124 (10)	0.040 (2)	0.611 (3)
H4C1	−0.1620	0.1627	−0.1244	0.060*	0.611 (3)
H4C2	−0.0241	0.1658	−0.1785	0.060*	0.611 (3)
H4C3	−0.0739	0.2196	−0.1090	0.060*	0.611 (3)
C5C	0.2059 (4)	0.14187 (17)	0.1426 (4)	0.0271 (10)	0.611 (3)
H5C1	0.2023	0.1005	0.1246	0.033*	0.611 (3)
H5C2	0.3007	0.1530	0.1573	0.033*	0.611 (3)
C6C	0.1447 (19)	0.1518 (9)	0.2535 (7)	0.029 (2)	0.611 (3)
H6C1	0.1928	0.1297	0.3187	0.044*	0.611 (3)
H6C2	0.0517	0.1396	0.2412	0.044*	0.611 (3)
H6C3	0.1495	0.1925	0.2735	0.044*	0.611 (3)
C7C	0.1441 (5)	0.23881 (17)	0.0576 (4)	0.0310 (11)	0.611 (3)
H7C1	0.1056	0.2565	−0.0183	0.037*	0.611 (3)
H7C2	0.0770	0.2443	0.1127	0.037*	0.611 (3)
C8C	0.2393 (7)	0.2726 (3)	0.0975 (11)	0.049 (2)	0.611 (3)
H8C1	0.2046	0.3114	0.1036	0.074*	0.611 (3)
H8C2	0.3069	0.2725	0.0431	0.074*	0.611 (3)
H8C3	0.2789	0.2596	0.1762	0.074*	0.611 (3)
C1C'	0.1829 (7)	0.1151 (3)	0.0039 (6)	0.0313 (17)	0.389 (3)
H1C3	0.2515	0.1028	0.0687	0.038*	0.389 (3)
H1C4	0.1058	0.0893	0.0049	0.038*	0.389 (3)
C2C'	0.237 (4)	0.1069 (13)	−0.112 (3)	0.0409 (18)	0.389 (3)
H2C4	0.2643	0.0670	−0.1196	0.061*	0.389 (3)
H2C5	0.3141	0.1319	−0.1150	0.061*	0.389 (3)
H2C6	0.1685	0.1164	−0.1781	0.061*	0.389 (3)
C3C'	0.0367 (7)	0.1966 (3)	−0.0737 (6)	0.0302 (16)	0.389 (3)
H3C3	0.0068	0.2353	−0.0539	0.036*	0.389 (3)
H3C4	0.0820	0.2000	−0.1457	0.036*	0.389 (3)
C4C'	−0.0849 (16)	0.1587 (7)	−0.1027 (18)	0.040 (2)	0.389 (3)
H4C4	−0.1428	0.1749	−0.1701	0.060*	0.389 (3)
H4C5	−0.1333	0.1566	−0.0334	0.060*	0.389 (3)
H4C6	−0.0569	0.1203	−0.1232	0.060*	0.389 (3)
C5C'	0.0653 (6)	0.1730 (3)	0.1398 (5)	0.0225 (14)	0.389 (3)
H5C3	0.0202	0.2101	0.1467	0.027*	0.389 (3)
H5C4	−0.0039	0.1431	0.1273	0.027*	0.389 (3)
C6C'	0.152 (3)	0.1611 (15)	0.2544 (12)	0.029 (2)	0.389 (3)
H6C4	0.0982	0.1601	0.3199	0.044*	0.389 (3)
H6C5	0.2194	0.1913	0.2691	0.044*	0.389 (3)
H6C6	0.1967	0.1241	0.2491	0.044*	0.389 (3)
C7C'	0.2528 (6)	0.2158 (3)	0.0447 (6)	0.0274 (16)	0.389 (3)
H7C3	0.3307	0.1902	0.0616	0.033*	0.389 (3)
H7C4	0.2551	0.2291	−0.0378	0.033*	0.389 (3)
C8C'	0.2884 (13)	0.2594 (5)	0.1049 (17)	0.049 (2)	0.389 (3)
H8C4	0.3714	0.2741	0.0811	0.074*	0.389 (3)
H8C5	0.3021	0.2494	0.1895	0.074*	0.389 (3)
H8C6	0.2194	0.2888	0.0911	0.074*	0.389 (3)
N1S	0.0766 (3)	0.15711 (15)	0.6193 (3)	0.0686 (10)
C1S	0.1527 (3)	0.18783 (14)	0.5901 (3)	0.0407 (7)
C2S	0.2493 (3)	0.22731 (12)	0.5543 (3)	0.0404 (7)
H2S1	0.2060	0.2531	0.4933	0.061*
H2S2	0.3197	0.2060	0.5220	0.061*
H2S3	0.2879	0.2496	0.6233	0.061*
O1W	1.0262 (2)	0.29166 (9)	0.31420 (19)	0.0423 (5)
H1W1	1.034 (3)	0.3105 (13)	0.376 (2)	0.063*
H2W1	0.969 (3)	0.2672 (12)	0.318 (3)	0.063*
O2W	1.1073 (4)	−0.0035 (2)	0.0843 (4)	0.0494 (12)	0.50
H1W2	1.032 (4)	0.008 (3)	0.098 (6)	0.074*	0.50
H2W2	1.098 (7)	−0.010 (3)	0.011 (2)	0.074*	0.50

	U11	U22	U33	U12	U13	U23
Co1	0.0327 (2)	0.01501 (19)	0.0242 (2)	−0.00140 (14)	0.01285 (15)	−0.00014 (14)
N1	0.0272 (11)	0.0178 (10)	0.0289 (12)	−0.0035 (9)	0.0129 (9)	−0.0010 (9)
N2	0.0318 (12)	0.0179 (10)	0.0246 (12)	−0.0017 (9)	0.0120 (9)	−0.0022 (9)
C1	0.0329 (15)	0.0223 (13)	0.0335 (15)	−0.0050 (11)	0.0084 (12)	0.0009 (12)
C2	0.0467 (17)	0.0315 (16)	0.0353 (17)	−0.0054 (13)	0.0001 (14)	0.0007 (13)
C3	0.059 (2)	0.0351 (17)	0.0338 (17)	−0.0089 (15)	0.0020 (15)	0.0095 (14)
C4	0.0479 (17)	0.0244 (14)	0.0336 (16)	−0.0089 (13)	0.0081 (13)	0.0046 (12)
C5	0.0329 (14)	0.0190 (13)	0.0265 (14)	−0.0009 (11)	0.0126 (11)	−0.0009 (11)
C6	0.0332 (14)	0.0179 (12)	0.0231 (13)	−0.0008 (11)	0.0133 (11)	−0.0028 (10)
C7	0.0417 (16)	0.0185 (13)	0.0289 (15)	−0.0041 (11)	0.0162 (12)	−0.0008 (11)
C8	0.0396 (16)	0.0212 (13)	0.0376 (16)	−0.0090 (12)	0.0149 (13)	−0.0090 (12)
C9	0.0389 (16)	0.0281 (14)	0.0302 (15)	−0.0043 (12)	0.0076 (12)	−0.0081 (12)
C10	0.0416 (16)	0.0222 (14)	0.0253 (14)	0.0005 (12)	0.0094 (12)	−0.0015 (11)
N3	0.086 (2)	0.0285 (14)	0.078 (2)	0.0051 (14)	0.0623 (19)	0.0012 (14)
C11	0.0521 (18)	0.0173 (14)	0.0405 (17)	−0.0043 (12)	0.0255 (14)	0.0019 (12)
N4	0.0389 (13)	0.0227 (12)	0.0425 (14)	−0.0040 (11)	0.0167 (11)	0.0010 (10)
C12	0.0306 (14)	0.0215 (14)	0.0297 (14)	0.0042 (12)	0.0153 (11)	0.0035 (11)
N5	0.0548 (16)	0.0277 (13)	0.0315 (14)	−0.0001 (11)	0.0113 (12)	0.0055 (11)
C13	0.0422 (16)	0.0190 (13)	0.0299 (16)	−0.0052 (12)	0.0166 (13)	−0.0024 (12)
N6	0.0300 (12)	0.0221 (11)	0.0337 (13)	−0.0004 (9)	0.0100 (10)	−0.0031 (10)
C14	0.0287 (14)	0.0161 (12)	0.0227 (13)	−0.0052 (10)	0.0048 (11)	0.0003 (10)
N1C	0.0295 (11)	0.0203 (11)	0.0236 (11)	−0.0016 (9)	0.0087 (9)	0.0000 (9)
C1C	0.041 (3)	0.035 (3)	0.022 (2)	−0.007 (2)	0.0130 (19)	−0.0034 (19)
C2C	0.048 (4)	0.038 (3)	0.0396 (18)	0.006 (3)	0.015 (2)	−0.0112 (17)
C3C	0.028 (2)	0.036 (3)	0.029 (2)	−0.0050 (19)	0.0056 (18)	−0.006 (2)
C4C	0.042 (3)	0.049 (7)	0.028 (2)	0.003 (4)	0.000 (2)	0.002 (4)
C5C	0.031 (2)	0.021 (2)	0.028 (2)	0.0054 (18)	0.0038 (18)	0.0008 (18)
C6C	0.038 (2)	0.021 (7)	0.0286 (15)	0.004 (3)	0.0031 (14)	0.0039 (17)
C7C	0.046 (3)	0.020 (2)	0.027 (2)	0.0013 (19)	0.007 (2)	0.0004 (18)
C8C	0.080 (6)	0.029 (4)	0.048 (3)	−0.016 (4)	0.043 (5)	−0.016 (3)
C1C'	0.037 (4)	0.015 (3)	0.044 (4)	0.002 (3)	0.015 (3)	−0.006 (3)
C2C'	0.048 (4)	0.038 (3)	0.0396 (18)	0.006 (3)	0.015 (2)	−0.0112 (17)
C3C'	0.039 (4)	0.029 (4)	0.022 (3)	0.002 (3)	0.003 (3)	−0.001 (3)
C4C'	0.042 (3)	0.049 (7)	0.028 (2)	0.003 (4)	0.000 (2)	0.002 (4)
C5C'	0.022 (3)	0.021 (3)	0.027 (3)	0.000 (3)	0.011 (3)	0.006 (3)
C6C'	0.038 (2)	0.021 (7)	0.0286 (15)	0.004 (3)	0.0031 (14)	0.0039 (17)
C7C'	0.031 (4)	0.021 (3)	0.033 (4)	−0.007 (3)	0.012 (3)	−0.003 (3)
C8C'	0.080 (6)	0.029 (4)	0.048 (3)	−0.016 (4)	0.043 (5)	−0.016 (3)
N1S	0.078 (2)	0.082 (2)	0.0462 (18)	−0.045 (2)	0.0083 (16)	−0.0021 (16)
C1S	0.0477 (18)	0.0448 (18)	0.0296 (16)	−0.0135 (15)	0.0054 (14)	−0.0090 (14)
C2S	0.0436 (17)	0.0330 (16)	0.0486 (19)	−0.0068 (13)	0.0212 (15)	−0.0123 (14)
O1W	0.0548 (14)	0.0344 (12)	0.0429 (13)	−0.0221 (10)	0.0265 (11)	−0.0162 (10)
O2W	0.033 (2)	0.078 (3)	0.035 (2)	0.018 (2)	−0.0045 (19)	−0.015 (2)

Co1—C12	1.868 (3)	C4C—H4C1	0.9800
Co1—C13	1.869 (3)	C4C—H4C2	0.9800
Co1—C11	1.904 (3)	C4C—H4C3	0.9800
Co1—C14	1.904 (3)	C5C—C6C	1.490 (14)
Co1—N1	1.959 (2)	C5C—H5C1	0.9900
Co1—N2	1.966 (2)	C5C—H5C2	0.9900
N1—C1	1.347 (3)	C6C—H6C1	0.9800
N1—C5	1.356 (3)	C6C—H6C2	0.9800
N2—C10	1.337 (3)	C6C—H6C3	0.9800
N2—C6	1.354 (3)	C7C—C8C	1.286 (8)
C1—C2	1.385 (4)	C7C—H7C1	0.9900
C1—H1	0.9500	C7C—H7C2	0.9900
C2—C3	1.380 (4)	C8C—H8C1	0.9800
C2—H2	0.9500	C8C—H8C2	0.9800
C3—C4	1.386 (4)	C8C—H8C3	0.9800
C3—H3	0.9500	C1C'—C2C'	1.505 (19)
C4—C5	1.392 (4)	C1C'—H1C3	0.9900
C4—H4	0.9500	C1C'—H1C4	0.9900
C5—C6	1.469 (4)	C2C'—H2C4	0.9800
C6—C7	1.387 (3)	C2C'—H2C5	0.9800
C7—C8	1.379 (4)	C2C'—H2C6	0.9800
C7—H7	0.9500	C3C'—C4C'	1.522 (12)
C8—C9	1.383 (4)	C3C'—H3C3	0.9900
C8—H8	0.9500	C3C'—H3C4	0.9900
C9—C10	1.386 (4)	C4C'—H4C4	0.9800
C9—H9	0.9500	C4C'—H4C5	0.9800
C10—H10	0.9500	C4C'—H4C6	0.9800
N3—C11	1.147 (4)	C5C'—C6C'	1.504 (18)
N4—C12	1.155 (3)	C5C'—H5C3	0.9900
N5—C13	1.159 (3)	C5C'—H5C4	0.9900
N6—C14	1.151 (3)	C6C'—H6C4	0.9800
N1C—C3C	1.485 (4)	C6C'—H6C5	0.9800
N1C—C7C'	1.489 (6)	C6C'—H6C6	0.9800
N1C—C1C'	1.509 (6)	C7C'—C8C'	1.256 (11)
N1C—C5C'	1.521 (6)	C7C'—H7C3	0.9900
N1C—C7C	1.526 (4)	C7C'—H7C4	0.9900
N1C—C1C	1.528 (4)	C8C'—H8C4	0.9800
N1C—C5C	1.555 (4)	C8C'—H8C5	0.9800
N1C—C3C'	1.570 (7)	C8C'—H8C6	0.9800
C1C—C2C	1.506 (16)	N1S—C1S	1.136 (4)
C1C—H1C1	0.9900	C1S—C2S	1.443 (4)
C1C—H1C2	0.9900	C2S—H2S1	0.9800
C2C—H2C1	0.9800	C2S—H2S2	0.9800
C2C—H2C2	0.9800	C2S—H2S3	0.9800
C2C—H2C3	0.9800	O1W—H1W1	0.827 (18)
C3C—C4C	1.518 (9)	O1W—H2W1	0.821 (18)
C3C—H3C1	0.9900	O2W—H1W2	0.84 (2)
C3C—H3C2	0.9900	O2W—H2W2	0.84 (2)
C12—Co1—C13	87.23 (11)	H2C2—C2C—H2C3	109.5
C12—Co1—C11	89.91 (11)	N1C—C3C—C4C	114.4 (5)
C13—Co1—C11	88.80 (12)	N1C—C3C—H3C1	108.7
C12—Co1—C14	88.53 (10)	C4C—C3C—H3C1	108.7
C13—Co1—C14	90.20 (11)	N1C—C3C—H3C2	108.7
C11—Co1—C14	178.18 (10)	C4C—C3C—H3C2	108.7
C12—Co1—N1	95.18 (10)	H3C1—C3C—H3C2	107.6
C13—Co1—N1	177.20 (10)	C3C—C4C—H4C1	109.5
C11—Co1—N1	89.79 (11)	C3C—C4C—H4C2	109.5
C14—Co1—N1	91.28 (9)	H4C1—C4C—H4C2	109.5
C12—Co1—N2	177.28 (10)	C3C—C4C—H4C3	109.5
C13—Co1—N2	95.33 (10)	H4C1—C4C—H4C3	109.5
C11—Co1—N2	91.07 (10)	H4C2—C4C—H4C3	109.5
C14—Co1—N2	90.54 (9)	C6C—C5C—N1C	115.0 (7)
N1—Co1—N2	82.28 (8)	C6C—C5C—H5C1	108.5
C1—N1—C5	119.0 (2)	N1C—C5C—H5C1	108.5
C1—N1—Co1	126.39 (17)	C6C—C5C—H5C2	108.5
C5—N1—Co1	114.58 (17)	N1C—C5C—H5C2	108.5
C10—N2—C6	118.8 (2)	H5C1—C5C—H5C2	107.5
C10—N2—Co1	126.51 (17)	C5C—C6C—H6C1	109.5
C6—N2—Co1	114.64 (17)	C5C—C6C—H6C2	109.5
N1—C1—C2	122.0 (2)	H6C1—C6C—H6C2	109.5
N1—C1—H1	119.0	C5C—C6C—H6C3	109.5
C2—C1—H1	119.0	H6C1—C6C—H6C3	109.5
C3—C2—C1	119.1 (3)	H6C2—C6C—H6C3	109.5
C3—C2—H2	120.4	C8C—C7C—N1C	132.3 (5)
C1—C2—H2	120.4	C8C—C7C—H7C1	104.2
C2—C3—C4	119.4 (3)	N1C—C7C—H7C1	104.2
C2—C3—H3	120.3	C8C—C7C—H7C2	104.2
C4—C3—H3	120.3	N1C—C7C—H7C2	104.2
C3—C4—C5	119.1 (3)	H7C1—C7C—H7C2	105.5
C3—C4—H4	120.5	C7C—C8C—H8C1	109.5
C5—C4—H4	120.5	C7C—C8C—H8C2	109.5
N1—C5—C4	121.4 (2)	H8C1—C8C—H8C2	109.5
N1—C5—C6	114.4 (2)	C7C—C8C—H8C3	109.5
C4—C5—C6	124.2 (2)	H8C1—C8C—H8C3	109.5
N2—C6—C7	121.4 (2)	H8C2—C8C—H8C3	109.5
N2—C6—C5	114.1 (2)	C2C'—C1C'—N1C	116.7 (14)
C7—C6—C5	124.5 (2)	C2C'—C1C'—H1C3	108.1
C8—C7—C6	119.4 (2)	N1C—C1C'—H1C3	108.1
C8—C7—H7	120.3	C2C'—C1C'—H1C4	108.1
C6—C7—H7	120.3	N1C—C1C'—H1C4	108.1
C7—C8—C9	119.2 (2)	H1C3—C1C'—H1C4	107.3
C7—C8—H8	120.4	C1C'—C2C'—H2C4	109.5
C9—C8—H8	120.4	C1C'—C2C'—H2C5	109.5
C8—C9—C10	118.7 (3)	H2C4—C2C'—H2C5	109.5
C8—C9—H9	120.7	C1C'—C2C'—H2C6	109.5
C10—C9—H9	120.7	H2C4—C2C'—H2C6	109.5
N2—C10—C9	122.5 (2)	H2C5—C2C'—H2C6	109.5
N2—C10—H10	118.8	C4C'—C3C'—N1C	114.8 (8)
C9—C10—H10	118.8	C4C'—C3C'—H3C3	108.6
N3—C11—Co1	179.5 (3)	N1C—C3C'—H3C3	108.6
N4—C12—Co1	179.4 (2)	C4C'—C3C'—H3C4	108.6
N5—C13—Co1	179.0 (3)	N1C—C3C'—H3C4	108.6
N6—C14—Co1	178.5 (2)	H3C3—C3C'—H3C4	107.5
C3C—N1C—C7C'	157.9 (4)	C3C'—C4C'—H4C4	109.5
C3C—N1C—C1C'	87.4 (3)	C3C'—C4C'—H4C5	109.5
C7C'—N1C—C1C'	112.1 (4)	H4C4—C4C'—H4C5	109.5
C3C—N1C—C5C'	66.9 (3)	C3C'—C4C'—H4C6	109.5
C7C'—N1C—C5C'	113.2 (4)	H4C4—C4C'—H4C6	109.5
C1C'—N1C—C5C'	109.2 (4)	H4C5—C4C'—H4C6	109.5
C3C—N1C—C7C	110.9 (3)	C6C'—C5C'—N1C	113.9 (12)
C7C'—N1C—C7C	49.2 (3)	C6C'—C5C'—H5C3	108.8
C1C'—N1C—C7C	161.2 (4)	N1C—C5C'—H5C3	108.8
C5C'—N1C—C7C	82.9 (3)	C6C'—C5C'—H5C4	108.8
C3C—N1C—C1C	113.1 (3)	N1C—C5C'—H5C4	108.8
C7C'—N1C—C1C	71.8 (3)	H5C3—C5C'—H5C4	107.7
C1C'—N1C—C1C	58.8 (3)	C5C'—C6C'—H6C4	109.5
C5C'—N1C—C1C	167.6 (3)	C5C'—C6C'—H6C5	109.5
C7C—N1C—C1C	107.9 (3)	H6C4—C6C'—H6C5	109.5
C3C—N1C—C5C	108.6 (3)	C5C'—C6C'—H6C6	109.5
C7C'—N1C—C5C	89.4 (3)	H6C4—C6C'—H6C6	109.5
C1C'—N1C—C5C	66.5 (3)	H6C5—C6C'—H6C6	109.5
C5C'—N1C—C5C	62.7 (3)	C8C'—C7C'—N1C	138.0 (9)
C7C—N1C—C5C	109.4 (3)	C8C'—C7C'—H7C3	102.6
C1C—N1C—C5C	106.9 (3)	N1C—C7C'—H7C3	102.6
C3C—N1C—C3C'	54.2 (3)	C8C'—C7C'—H7C4	102.6
C7C'—N1C—C3C'	107.4 (4)	N1C—C7C'—H7C4	102.6
C1C'—N1C—C3C'	109.0 (4)	H7C3—C7C'—H7C4	105.0
C5C'—N1C—C3C'	105.7 (4)	C7C'—C8C'—H8C4	109.5
C7C—N1C—C3C'	80.1 (3)	C7C'—C8C'—H8C5	109.5
C1C—N1C—C3C'	82.7 (3)	H8C4—C8C'—H8C5	109.5
C5C—N1C—C3C'	162.8 (3)	C7C'—C8C'—H8C6	109.5
C2C—C1C—N1C	115.4 (8)	H8C4—C8C'—H8C6	109.5
C2C—C1C—H1C1	108.4	H8C5—C8C'—H8C6	109.5
N1C—C1C—H1C1	108.4	N1S—C1S—C2S	179.2 (4)
C2C—C1C—H1C2	108.4	C1S—C2S—H2S1	109.5
N1C—C1C—H1C2	108.4	C1S—C2S—H2S2	109.5
H1C1—C1C—H1C2	107.5	H2S1—C2S—H2S2	109.5
C1C—C2C—H2C1	109.5	C1S—C2S—H2S3	109.5
C1C—C2C—H2C2	109.5	H2S1—C2S—H2S3	109.5
H2C1—C2C—H2C2	109.5	H2S2—C2S—H2S3	109.5
C1C—C2C—H2C3	109.5	H1W1—O1W—H2W1	108 (3)
H2C1—C2C—H2C3	109.5	H1W2—O2W—H2W2	105 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···N5i	0.83 (2)	2.10 (2)	2.925 (3)	176 (3)
O1W—H2W1···N4	0.82 (2)	2.08 (2)	2.899 (3)	174 (3)
O2W—H1W2···N3	0.84 (2)	1.83 (2)	2.665 (5)	172 (7)
O2W—H2W2···N3ii	0.84 (2)	1.92 (2)	2.740 (5)	165 (7)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯N5i	0.83 (2)	2.10 (2)	2.925 (3)	176 (3)
O1W—H2W1⋯N4	0.82 (2)	2.08 (2)	2.899 (3)	174 (3)
O2W—H1W2⋯N3	0.84 (2)	1.83 (2)	2.665 (5)	172 (7)
O2W—H2W2⋯N3ii	0.84 (2)	1.92 (2)	2.740 (5)	165 (7)

Symmetry codes: (i) ; (ii) .