Tetrakis(4-acetyl­pyridine)­diiso­thio­cyanato­cobalt(II)

The title compound, [Co(NCS)₂(C₇H₇NO)₄], was synthesized and its molecular structure was precisely characterized by low-temperature single-crystal analysis. The central cobalt ion has an octahedral coordination environment.

Key indicators

• Single-crystal X-ray study
• T = 110 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.046
• wR factor = 0.115
• Data-to-parameter ratio = 19.1

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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S1. Comment

It has been demonstrated during the last few decades that halido or pseudo-halido complexes of cobalt(II) that contain pyridines and substituted pyridines undergo a series of interesting solid-state reactions (Agnew et al., 1974; Liptay et al., 1992). These complexes also exhibited selective enclathration of other species (Schaeffer et al., 1957). Extensive differential scanning calorimetry and optical microscopic studies were carried out on the solid-state reactions of cobalt(II) pseudo-halido complexes containing substituted pyridines (Agnew & Brown, 1974). In the observed structure, the central Co atom is six-coordinate to four equatorial pyridyl donors and two axial thiocyanates, forming an octahedral structure.

S2. Experimental

Ethylenediamine, 4-acetyl pyridine and cobalt(II) thiocyanate were obtained from Aldrich. The N,N'-bis(4-acetylpyrilidene)ethylenediamine component was prepared in the following manner: 1 ml (15 mmol) of distilled ethylenediamine and 3.32 ml (30 mmol) of freshly distilled 4-acetylpyridine) were refluxed in 50 ml of anhydrous methanol for 6 h. On evaporation of the solvent, a yellow semi-solid was obtained, which on recrystallization from n-hexane gave colorless needles of N,N'-bis(4-acetylpyrilidene)ethylenediamine. Yield: 2.30 g (58%); m.p. 446–448 K. Analysis found (calculated): C 72.29 (72.14), H 6.92 (6.82), N 20.97% (21.04%). EI—MS: m/z 267.1 (MH⁺, 90%), 237.1 (MH⁺ - 2CH₃, 12%). ¹H NMR (200 MHz, CDCl₃, TMS): δ 8.64 (d, J = 4 Hz, 4H), 7.60 (d, J = 4 Hz, 4H), 3.94 (s, methylene, 4H), 2.28 (s, methyl, 6H). ¹³C NMR (200 MHz, CDCl₃, TMS): δ 164.54, 150.14, 147.74, 121.19, 53.35, 15.66. 0.13 g (0.5 mmol) of the latter product was dissolved in 30 ml me thanol, and added 10 ml water solution of 0.09 g (0.5 mmol) cobalt(II) thiocyanate with constant stirring. The resulting red–yellow solution was kept in the refrigerator for three days until yellow crystals of the title compound separated out. They were filtered off and dried in air. Yield: 0.15 g (45%).

Computing details

Data collection: COLLECT (Nonius B.V., 1999); cell refinement: DENZO (Otwinowski, 1985); data reduction: DENZO (Otwinowski, 1985); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. The molecular structure of the title compound. Ellipsoids are shown at the 50% probability level at 110 K. The coordination distances to the metal ion are: Co1—N2 2.067 (2), Co1—N5 2.072 (2), Co1—N8 2.183 (2), Co1—N17 2.224 (2), Co1—N26 2.205 (2) and Co1—N35 2.153 (2) Å.
	Fig. 2. The crystal packing viewed down the b axis of the crystal (a is horizontal and c is vertical). Atoms are shown as arbitrarily sized spheres; all non-C atoms are denoted by crossed circles.

Tetrakis(4-acetylpyridine)diisothiocyanatocobalt(II)

Crystal data

[Co(NCS)2(C7H7NO)4]	Dx = 1.387 Mg m^−3
Mr = 659.63	Melting point: 173-175 °C K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
a = 11.9180 (2) Å	Cell parameters from 4541 reflections
b = 15.9700 (2) Å	θ = 2.8–27.9°
c = 33.1930 (6) Å	µ = 0.72 mm^−1
V = 6317.64 (17) Å^3	T = 110 K
Z = 8	Prism, yellow-red
F(000) = 2728	0.25 × 0.20 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer	7506 independent reflections
Radiation source: fine-focus sealed tube	4541 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.063
Detector resolution: 56 microns pixels mm^-1	θmax = 27.9°, θmin = 2.8°
1.0° ϕ scans	h = 0→15
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = 0→20
Tmin = 0.841, Tmax = 0.932	l = 0→43
14852 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.115	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0525P)^2 + 0.1175P] where P = (Fo^2 + 2Fc^2)/3
7506 reflections	(Δ/σ)max = 0.010
392 parameters	Δρmax = 0.38 e Å^−3
0 restraints	Δρmin = −0.39 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Co1	0.44893 (3)	0.061308 (19)	0.130607 (10)	0.02267 (11)
N2	0.49857 (18)	−0.05290 (12)	0.10731 (7)	0.0289 (5)
C3	0.5356 (2)	−0.11995 (16)	0.10372 (7)	0.0263 (6)
S4	0.59144 (7)	−0.21263 (4)	0.09935 (2)	0.0429 (2)
N5	0.40083 (17)	0.17406 (12)	0.15618 (6)	0.0263 (5)
C6	0.3562 (2)	0.22487 (15)	0.17532 (8)	0.0242 (6)
S7	0.29491 (6)	0.29716 (5)	0.20202 (2)	0.0409 (2)
N8	0.27963 (17)	0.04679 (11)	0.10652 (6)	0.0239 (5)
C9	0.2154 (2)	0.11319 (15)	0.09877 (7)	0.0278 (6)
H9	0.2428	0.1670	0.1060	0.033*
C10	0.1111 (2)	0.10797 (15)	0.08075 (8)	0.0272 (6)
H10	0.0687	0.1572	0.0757	0.033*
C11	0.0692 (2)	0.03039 (15)	0.07009 (8)	0.0258 (6)
C12	0.1343 (2)	−0.03966 (15)	0.07908 (8)	0.0315 (6)
H12	0.1079	−0.0942	0.0728	0.038*
C13	0.2376 (2)	−0.02884 (15)	0.09729 (8)	0.0310 (6)
H13	0.2809	−0.0771	0.1036	0.037*
C14	−0.0407 (2)	0.01980 (17)	0.04860 (8)	0.0329 (6)
C15	−0.0980 (2)	0.09532 (17)	0.03205 (9)	0.0419 (8)
H15A	−0.1655	0.0782	0.0173	0.063*
H15B	−0.0470	0.1248	0.0137	0.063*
H15C	−0.1191	0.1327	0.0542	0.063*
O16	−0.08074 (17)	−0.04936 (12)	0.04459 (7)	0.0525 (6)
N17	0.62281 (17)	0.08328 (12)	0.15254 (6)	0.0241 (5)
C18	0.6445 (2)	0.13397 (15)	0.18366 (8)	0.0280 (6)
H18	0.5829	0.1566	0.1982	0.034*
C19	0.7526 (2)	0.15539 (15)	0.19589 (8)	0.0286 (6)
H19	0.7642	0.1930	0.2177	0.034*
C20	0.8428 (2)	0.12062 (15)	0.17556 (8)	0.0266 (6)
C21	0.8209 (2)	0.06782 (15)	0.14359 (8)	0.0283 (6)
H21	0.8811	0.0431	0.1291	0.034*
C22	0.7112 (2)	0.05100 (15)	0.13268 (8)	0.0272 (6)
H22	0.6978	0.0153	0.1103	0.033*
C23	0.9632 (2)	0.13682 (17)	0.18784 (8)	0.0331 (7)
C24	0.9890 (2)	0.21469 (19)	0.21046 (10)	0.0475 (8)
H24A	1.0705	0.2205	0.2133	0.071*
H24B	0.9545	0.2119	0.2372	0.071*
H24C	0.9591	0.2630	0.1958	0.071*
O25	1.03449 (16)	0.08539 (13)	0.17840 (6)	0.0471 (5)
N26	0.51032 (17)	0.12610 (12)	0.07626 (6)	0.0253 (5)
C27	0.5373 (2)	0.08720 (16)	0.04180 (8)	0.0295 (6)
H27	0.5118	0.0314	0.0379	0.035*
C28	0.6000 (2)	0.12373 (16)	0.01176 (8)	0.0311 (6)
H28	0.6154	0.0938	−0.0123	0.037*
C29	0.6405 (2)	0.20443 (15)	0.01680 (8)	0.0273 (6)
C30	0.6113 (2)	0.24601 (16)	0.05182 (8)	0.0329 (7)
H30	0.6363	0.3017	0.0564	0.039*
C31	0.5456 (2)	0.20573 (15)	0.08011 (8)	0.0295 (6)
H31	0.5242	0.2359	0.1035	0.035*
C32	0.7193 (2)	0.24147 (16)	−0.01386 (9)	0.0341 (7)
C33	0.7771 (2)	0.32178 (17)	−0.00378 (9)	0.0404 (7)
H33A	0.8252	0.3385	−0.0263	0.061*
H33B	0.8230	0.3141	0.0204	0.061*
H33C	0.7209	0.3654	0.0012	0.061*
O34	0.73596 (18)	0.20415 (11)	−0.04543 (6)	0.0469 (6)
N35	0.40096 (17)	0.00254 (11)	0.18639 (6)	0.0239 (5)
C36	0.3011 (2)	0.01651 (15)	0.20425 (8)	0.0251 (6)
H36	0.2482	0.0515	0.1911	0.030*
C37	0.2731 (2)	−0.01791 (14)	0.24070 (7)	0.0231 (6)
H37	0.2008	−0.0085	0.2518	0.028*
C38	0.3510 (2)	−0.06675 (14)	0.26139 (7)	0.0232 (6)
C39	0.4547 (2)	−0.07981 (14)	0.24344 (8)	0.0247 (6)
H39	0.5108	−0.1115	0.2569	0.030*
C40	0.4753 (2)	−0.04655 (14)	0.20614 (8)	0.0262 (6)
H40	0.5451	−0.0585	0.1936	0.031*
C41	0.3187 (2)	−0.10567 (15)	0.30053 (8)	0.0297 (6)
C42	0.4093 (2)	−0.13244 (18)	0.32917 (9)	0.0410 (7)
H42A	0.3758	−0.1470	0.3552	0.061*
H42B	0.4628	−0.0865	0.3328	0.061*
H42C	0.4484	−0.1813	0.3182	0.061*
O43	0.21969 (16)	−0.11513 (12)	0.30880 (6)	0.0422 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co1	0.01944 (18)	0.01858 (18)	0.0300 (2)	0.00088 (14)	−0.00031 (15)	−0.00206 (15)
N2	0.0232 (12)	0.0234 (12)	0.0401 (14)	0.0011 (10)	0.0020 (11)	−0.0046 (10)
C3	0.0250 (14)	0.0275 (14)	0.0265 (15)	−0.0053 (11)	0.0027 (11)	−0.0044 (12)
S4	0.0518 (5)	0.0240 (4)	0.0528 (5)	0.0076 (3)	0.0060 (4)	−0.0073 (3)
N5	0.0226 (12)	0.0230 (11)	0.0333 (13)	0.0003 (9)	0.0014 (10)	−0.0017 (10)
C6	0.0194 (13)	0.0225 (13)	0.0308 (15)	−0.0060 (11)	−0.0024 (11)	0.0029 (12)
S7	0.0284 (4)	0.0375 (4)	0.0568 (5)	0.0007 (3)	0.0065 (4)	−0.0201 (4)
N8	0.0225 (12)	0.0198 (11)	0.0293 (12)	−0.0004 (9)	−0.0007 (10)	−0.0009 (9)
C9	0.0294 (15)	0.0218 (13)	0.0321 (15)	−0.0013 (11)	−0.0051 (12)	0.0008 (12)
C10	0.0267 (15)	0.0224 (13)	0.0325 (15)	0.0056 (11)	−0.0016 (12)	−0.0029 (12)
C11	0.0230 (14)	0.0275 (14)	0.0269 (14)	−0.0006 (11)	0.0010 (11)	−0.0011 (12)
C12	0.0286 (15)	0.0200 (13)	0.0459 (17)	−0.0014 (11)	−0.0063 (13)	−0.0051 (12)
C13	0.0277 (15)	0.0225 (13)	0.0429 (17)	0.0032 (11)	−0.0060 (13)	−0.0022 (12)
C14	0.0271 (15)	0.0350 (16)	0.0364 (16)	0.0026 (13)	−0.0002 (13)	−0.0099 (13)
C15	0.0362 (17)	0.0373 (16)	0.052 (2)	0.0065 (14)	−0.0148 (15)	−0.0069 (15)
O16	0.0371 (13)	0.0337 (12)	0.0867 (17)	−0.0055 (9)	−0.0227 (12)	−0.0067 (11)
N17	0.0220 (12)	0.0223 (11)	0.0280 (12)	−0.0004 (9)	−0.0002 (10)	−0.0002 (10)
C18	0.0243 (15)	0.0279 (14)	0.0318 (16)	0.0006 (11)	0.0002 (12)	0.0020 (12)
C19	0.0261 (15)	0.0253 (14)	0.0344 (16)	−0.0029 (11)	−0.0047 (12)	−0.0025 (12)
C20	0.0219 (14)	0.0272 (13)	0.0306 (15)	−0.0014 (11)	−0.0014 (12)	0.0086 (12)
C21	0.0216 (14)	0.0310 (14)	0.0324 (15)	0.0031 (11)	0.0036 (11)	0.0022 (13)
C22	0.0254 (14)	0.0275 (14)	0.0286 (15)	0.0002 (11)	0.0014 (12)	0.0014 (12)
C23	0.0242 (15)	0.0388 (16)	0.0362 (16)	−0.0022 (13)	−0.0026 (12)	0.0055 (14)
C24	0.0280 (17)	0.058 (2)	0.057 (2)	−0.0090 (15)	−0.0049 (15)	−0.0119 (17)
O25	0.0237 (11)	0.0491 (12)	0.0683 (15)	0.0035 (10)	−0.0051 (10)	−0.0026 (11)
N26	0.0231 (12)	0.0223 (11)	0.0306 (13)	0.0013 (9)	−0.0036 (10)	−0.0002 (10)
C27	0.0281 (15)	0.0273 (13)	0.0331 (16)	−0.0006 (11)	−0.0049 (13)	−0.0052 (13)
C28	0.0316 (16)	0.0318 (15)	0.0298 (16)	0.0049 (12)	0.0025 (12)	−0.0055 (13)
C29	0.0270 (15)	0.0257 (13)	0.0292 (15)	0.0068 (11)	−0.0010 (12)	0.0018 (12)
C30	0.0390 (17)	0.0220 (13)	0.0377 (17)	−0.0028 (12)	0.0043 (13)	0.0019 (13)
C31	0.0372 (16)	0.0232 (14)	0.0281 (15)	0.0024 (12)	0.0035 (13)	−0.0001 (12)
C32	0.0316 (16)	0.0331 (15)	0.0376 (17)	0.0093 (13)	0.0048 (13)	0.0085 (14)
C33	0.0343 (17)	0.0467 (18)	0.0404 (18)	−0.0040 (14)	0.0068 (14)	0.0092 (14)
O34	0.0661 (16)	0.0357 (11)	0.0389 (12)	0.0103 (10)	0.0177 (11)	0.0005 (10)
N35	0.0196 (11)	0.0203 (11)	0.0317 (12)	−0.0007 (9)	−0.0037 (9)	−0.0009 (9)
C36	0.0166 (13)	0.0222 (13)	0.0364 (16)	−0.0004 (10)	−0.0020 (12)	−0.0020 (12)
C37	0.0172 (13)	0.0200 (13)	0.0322 (15)	0.0020 (10)	0.0008 (11)	−0.0036 (12)
C38	0.0216 (14)	0.0194 (12)	0.0286 (14)	−0.0006 (10)	−0.0001 (11)	−0.0048 (11)
C39	0.0171 (13)	0.0229 (13)	0.0340 (15)	0.0000 (10)	−0.0032 (11)	0.0015 (11)
C40	0.0201 (13)	0.0229 (13)	0.0357 (16)	0.0013 (10)	0.0006 (12)	−0.0008 (12)
C41	0.0290 (16)	0.0253 (14)	0.0348 (16)	0.0055 (12)	0.0027 (13)	−0.0022 (12)
C42	0.0371 (17)	0.0470 (17)	0.0388 (18)	0.0139 (14)	0.0059 (14)	0.0097 (15)
O43	0.0306 (12)	0.0510 (13)	0.0451 (12)	0.0086 (9)	0.0115 (9)	0.0136 (10)

Geometric parameters (Å, º)

Co1—N2	2.067 (2)	C23—O25	1.223 (3)
Co1—N5	2.072 (2)	C23—C24	1.485 (4)
Co1—N35	2.153 (2)	C24—H24A	0.9800
Co1—N8	2.183 (2)	C24—H24B	0.9800
Co1—N26	2.205 (2)	C24—H24C	0.9800
Co1—N17	2.224 (2)	N26—C27	1.341 (3)
N2—C3	1.164 (3)	N26—C31	1.346 (3)
C3—S4	1.629 (3)	C27—C28	1.375 (4)
N5—C6	1.160 (3)	C27—H27	0.9500
C6—S7	1.628 (3)	C28—C29	1.386 (3)
N8—C9	1.333 (3)	C28—H28	0.9500
N8—C13	1.343 (3)	C29—C30	1.383 (3)
C9—C10	1.382 (3)	C29—C32	1.506 (4)
C9—H9	0.9500	C30—C31	1.382 (3)
C10—C11	1.382 (3)	C30—H30	0.9500
C10—H10	0.9500	C31—H31	0.9500
C11—C12	1.394 (3)	C32—O34	1.222 (3)
C11—C14	1.501 (4)	C32—C33	1.494 (4)
C12—C13	1.383 (3)	C33—H33A	0.9800
C12—H12	0.9500	C33—H33B	0.9800
C13—H13	0.9500	C33—H33C	0.9800
C14—O16	1.211 (3)	N35—C36	1.348 (3)
C14—C15	1.491 (4)	N35—C40	1.353 (3)
C15—H15A	0.9800	C36—C37	1.370 (3)
C15—H15B	0.9800	C36—H36	0.9500
C15—H15C	0.9800	C37—C38	1.394 (3)
N17—C18	1.338 (3)	C37—H37	0.9500
N17—C22	1.345 (3)	C38—C39	1.387 (3)
C18—C19	1.394 (3)	C38—C41	1.491 (4)
C18—H18	0.9500	C39—C40	1.369 (4)
C19—C20	1.385 (3)	C39—H39	0.9500
C19—H19	0.9500	C40—H40	0.9500
C20—C21	1.380 (4)	C41—O43	1.221 (3)
C20—C23	1.514 (4)	C41—C42	1.500 (4)
C21—C22	1.382 (3)	C42—H42A	0.9800
C21—H21	0.9500	C42—H42B	0.9800
C22—H22	0.9500	C42—H42C	0.9800
N2—Co1—N5	177.75 (9)	O25—C23—C24	123.2 (3)
N2—Co1—N35	90.75 (8)	O25—C23—C20	118.4 (2)
N5—Co1—N35	87.31 (8)	C24—C23—C20	118.4 (2)
N2—Co1—N8	91.94 (8)	C23—C24—H24A	109.5
N5—Co1—N8	89.23 (8)	C23—C24—H24B	109.5
N35—Co1—N8	91.33 (8)	H24A—C24—H24B	109.5
N2—Co1—N26	90.75 (8)	C23—C24—H24C	109.5
N5—Co1—N26	91.10 (8)	H24A—C24—H24C	109.5
N35—Co1—N26	175.12 (8)	H24B—C24—H24C	109.5
N8—Co1—N26	93.26 (7)	C27—N26—C31	116.4 (2)
N2—Co1—N17	89.71 (8)	C27—N26—Co1	124.08 (16)
N5—Co1—N17	89.23 (8)	C31—N26—Co1	118.01 (16)
N35—Co1—N17	91.99 (7)	N26—C27—C28	123.5 (2)
N8—Co1—N17	176.27 (7)	N26—C27—H27	118.2
N26—Co1—N17	83.37 (7)	C28—C27—H27	118.2
C3—N2—Co1	163.3 (2)	C27—C28—C29	119.7 (2)
N2—C3—S4	178.1 (2)	C27—C28—H28	120.1
C6—N5—Co1	163.64 (19)	C29—C28—H28	120.1
N5—C6—S7	179.2 (2)	C30—C29—C28	117.4 (2)
C9—N8—C13	117.2 (2)	C30—C29—C32	122.4 (2)
C9—N8—Co1	121.14 (16)	C28—C29—C32	120.1 (2)
C13—N8—Co1	121.57 (16)	C29—C30—C31	119.3 (2)
N8—C9—C10	123.5 (2)	C29—C30—H30	120.3
N8—C9—H9	118.2	C31—C30—H30	120.3
C10—C9—H9	118.2	N26—C31—C30	123.5 (2)
C11—C10—C9	119.4 (2)	N26—C31—H31	118.2
C11—C10—H10	120.3	C30—C31—H31	118.2
C9—C10—H10	120.3	O34—C32—C33	122.4 (2)
C10—C11—C12	117.6 (2)	O34—C32—C29	119.3 (2)
C10—C11—C14	122.6 (2)	C33—C32—C29	118.3 (2)
C12—C11—C14	119.8 (2)	C32—C33—H33A	109.5
C13—C12—C11	119.3 (2)	C32—C33—H33B	109.5
C13—C12—H12	120.4	H33A—C33—H33B	109.5
C11—C12—H12	120.4	C32—C33—H33C	109.5
N8—C13—C12	122.9 (2)	H33A—C33—H33C	109.5
N8—C13—H13	118.5	H33B—C33—H33C	109.5
C12—C13—H13	118.5	C36—N35—C40	117.5 (2)
O16—C14—C15	121.1 (3)	C36—N35—Co1	122.71 (16)
O16—C14—C11	119.9 (2)	C40—N35—Co1	119.70 (17)
C15—C14—C11	118.9 (2)	N35—C36—C37	122.5 (2)
C14—C15—H15A	109.5	N35—C36—H36	118.8
C14—C15—H15B	109.5	C37—C36—H36	118.8
H15A—C15—H15B	109.5	C36—C37—C38	119.8 (2)
C14—C15—H15C	109.5	C36—C37—H37	120.1
H15A—C15—H15C	109.5	C38—C37—H37	120.1
H15B—C15—H15C	109.5	C39—C38—C37	117.8 (2)
C18—N17—C22	117.3 (2)	C39—C38—C41	122.8 (2)
C18—N17—Co1	121.90 (16)	C37—C38—C41	119.4 (2)
C22—N17—Co1	120.58 (16)	C40—C39—C38	119.3 (2)
N17—C18—C19	123.5 (2)	C40—C39—H39	120.3
N17—C18—H18	118.2	C38—C39—H39	120.3
C19—C18—H18	118.2	N35—C40—C39	123.0 (2)
C20—C19—C18	118.5 (2)	N35—C40—H40	118.5
C20—C19—H19	120.8	C39—C40—H40	118.5
C18—C19—H19	120.8	O43—C41—C38	119.8 (2)
C21—C20—C19	118.2 (2)	O43—C41—C42	121.2 (2)
C21—C20—C23	119.4 (2)	C38—C41—C42	119.0 (2)
C19—C20—C23	122.4 (2)	C41—C42—H42A	109.5
C22—C21—C20	119.9 (2)	C41—C42—H42B	109.5
C22—C21—H21	120.0	H42A—C42—H42B	109.5
C20—C21—H21	120.0	C41—C42—H42C	109.5
N17—C22—C21	122.5 (2)	H42A—C42—H42C	109.5
N17—C22—H22	118.7	H42B—C42—H42C	109.5
C21—C22—H22	118.7