Tris(aceto­nitrile-κN)dichlorido(tri­phenyl­phosphane-κP)ruthenium(II) aceto­nitrile monosolvate

In the title complex, [RuCl₂(CH₃CN)₃(C₁₈H₁₅P)]·CH₃CN, the coordination geometry of the Ru^II atom is distorted octa­hedral, defined by one P atom from a tri­phenyl­phosphane ligand, three N atoms from three aceto­nitrile ligands and two Cl atoms. The three acetronitile ligands linearly bind to the Ru^II atom, with Ru—N—C angles of 172.6 (2), 179.9 (2) and 171.4 (2)°.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.025
• wR factor = 0.063
• Data-to-parameter ratio = 17.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors of          C7
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          1
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         27
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          1

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF          ?
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Ru1    --  Cl1     ..        7.3 su
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Ru1    --  Cl2     ..       12.3 su
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Ru1    --  N1      ..        6.1 su
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Ru1    --  N2      ..        7.2 su

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   5 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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S1. Comment

The structural and reactivity studies of coordinatively unsaturated ruthenium complexes have received much attention due to their versatile and diverse applications in organic transformation (Jansen et al., 2000; Trost et al., 2001). Since Stephenson & Wilkinson (1966) reported [RuCl₂(PPh₃)₃], it has been found that such five-coordinated ruthenium(II) complex readily loses one triphenylphosphane ligand in solution to give a six-coordinated ruthenium(II) complex with a [Ru(PPh₃)₂] moiety (Caulton, 1974). For example, two isomers of [RuCl₂(CH₃CN)₂(PPh₃)₂] were easily obtained upon refluxing [RuCl₂(PPh₃)₃] in a mixed solution with acetonitrile as both co-solvent and ligand (Al-Far & Slaughter, 2008; Gilbert & Wilkinson, 1969), which were firstly characterized by infrared spectroscopy (Hallman et al., 1970) and later confirmed by X-ray crystallography (Al-Far & Slaughter, 2008). We found that a similar reaction of [RuCl₂(PPh₃)₃] in the presence of equal equivalent of hydrogen peroxide resulted in loss of two triphenylphosphane ligands and coordination of three acetonitrile ligands. In this paper, we report the synthesis and crystal structure of a new ruthenium(II) complex [RuCl₂(CH₃CN)₃(PPh₃)].CH₃CN with a [Ru(PPh₃)] species.

In the title complex, the coordination geometry of the Ru^II atom is a distorted octahedral with one triphenylphosphane, three acetonitriles and two chlorides (Fig. 1). The average Ru—N bond distance value, 2.014 (2) Å, is similar to that found in cis-[RuCl₂(CH₃CN)₂(PPh₃)₂] [av. 2.010 (2) Å] (Al-Far & Slaughter, 2008). The Ru—N bond distance of the CH₃CN ligand trans to the chloride ligand is not extended (Jansen et al., 2000; Naskar & Bhattacharjee, 2005). Three CH₃CN ligands are coordinated linearly to the Ru^II atom with average Ru—N—C and N—C—C angles of 174.6 (2)° and 177.3 (2)°, respectively. Average Ru—Cl bond distance [2.4542 (6) Å] is as expected (Al-Far & Slaughter, 2008; Jansen et al., 2000). The Ru—P bond length of 2.2754 (6) Å in the title complex is slightly shorter than those of 2.3688 (7) and 2.3887 (7) Å in the complex cis-[RuCl₂(CH₃CN)₂(PPh₃)₂]. It is interesting to note that the Ru1—Cl2 bond [2.5007 (6) Å] trans to the PPh₃ ligand is ca. 0.1 Å longer than the Ru1—Cl1 bond [2.4080 (6)Å] trans to the CH₃CN ligand. The elongation of the Ru—Cl bond trans to the phosphane ligand is probably due to a relatively strong σ back-bonding from phosphrous to ruthenium.

Related literature

For background to ruthenium complexes, see: Caulton (1974); Gilbert & Wilkinson (1969); Hallman et al. (1970); Jansen et al. (2000); Stephenson & Wilkinson (1966); Trost et al. (2001). For related structures, see: Al-Far & Slaughter (2008); Naskar & Bhattacharjee (2005).

S2. Experimental

[RuCl₂(PPh₃)₃] (191 mg, 0.2 mmol) was dissolved in a freshly distilled CH₃CN (10 ml), with stirring at room temperature for 30 min. During this time, the color of the solution was changed from dark brown to orange. Hydrogen peroxide (30%, 6.8 ml, 0.2 mmol) was added to the solution and then the reaction mixture was stirred at reflux for 15 min, developing a yellow. The solvent was evaporated in vacuo and the yellow residue was washed with diethyl ether. Recrystallization from CH₃CN/Et₂O afforded yellow crystals of the title complex within five days. Yield: 127 mg, 69% (based on Ru). Analysis, calculated for C₂₆H₂₇Cl₂N₄PRu: C 52.18, H 4.55, N 9.36%; found C 52.13, H 4.51, N 9.39%.

S3. Refinement

H atoms were placed in geometrically idealized positions and refined as riding atoms, with C—H = 0.93 (aromatic) and 0.96 (methyl) Å and with U_iso(H) = 1.2(1.5 for methyl)U_eq(C).

Computing details

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Sheldrick, 2008).

Figures

Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.

Tris(acetonitrile-κN)dichlorido(triphenylphosphane-κP)ruthenium(II) acetonitrile monosolvate

Crystal data

[RuCl2(C2H3N)3(C18H15P)]·C2H3N	F(000) = 1216
Mr = 598.46	Dx = 1.439 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7259 reflections
a = 15.1133 (13) Å	θ = 2.4–29.4°
b = 13.9144 (12) Å	µ = 0.84 mm^−1
c = 13.3121 (12) Å	T = 296 K
β = 99.275 (2)°	Block, yellow
V = 2762.8 (4) Å^3	0.15 × 0.13 × 0.10 mm
Z = 4

Data collection

Bruker APEXII CCD diffractometer	5403 independent reflections
Radiation source: fine-focus sealed tube	4544 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
ϕ and ω scans	θmax = 26.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→16
Tmin = 0.884, Tmax = 0.921	k = −17→17
16271 measured reflections	l = −16→15

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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.063	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0223P)^2 + 1.1432P] where P = (Fo^2 + 2Fc^2)/3
5403 reflections	(Δ/σ)max = 0.001
311 parameters	Δρmax = 0.33 e Å^−3
0 restraints	Δρmin = −0.33 e Å^−3

Special details

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 > 2sigma(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
Ru1	0.392694 (11)	0.357317 (12)	0.697216 (12)	0.02730 (6)
Cl1	0.34706 (4)	0.31895 (4)	0.52005 (4)	0.04156 (14)
Cl2	0.55085 (4)	0.30921 (4)	0.68935 (5)	0.04180 (14)
P1	0.25036 (4)	0.40373 (4)	0.70896 (4)	0.03124 (13)
N1	0.42461 (13)	0.49189 (14)	0.65831 (14)	0.0346 (4)
N2	0.36584 (12)	0.22009 (13)	0.72988 (14)	0.0329 (4)
N3	0.43047 (12)	0.37894 (12)	0.84685 (14)	0.0309 (4)
N4	0.0609 (3)	0.6282 (3)	0.1682 (4)	0.1235 (15)
C1	0.43654 (16)	0.56570 (17)	0.62675 (17)	0.0371 (5)
C2	0.4461 (2)	0.66014 (18)	0.5837 (2)	0.0536 (7)
H2A	0.3951	0.6733	0.5325	0.080*
H2B	0.4997	0.6620	0.5536	0.080*
H2C	0.4498	0.7077	0.6364	0.080*
C3	0.35075 (16)	0.14273 (17)	0.74815 (18)	0.0380 (5)
C4	0.3303 (2)	0.04378 (19)	0.7712 (2)	0.0600 (8)
H4A	0.3235	0.0388	0.8415	0.090*
H4B	0.3782	0.0027	0.7584	0.090*
H4C	0.2755	0.0245	0.7290	0.090*
C5	0.44268 (16)	0.38452 (16)	0.93285 (18)	0.0361 (5)
C6	0.4521 (2)	0.3943 (2)	1.04268 (18)	0.0560 (8)
H6A	0.3952	0.4108	1.0611	0.084*
H6B	0.4948	0.4439	1.0652	0.084*
H6C	0.4725	0.3346	1.0743	0.084*
C7	0.1151 (3)	0.6798 (3)	0.1963 (3)	0.0899 (12)
C8	0.1863 (4)	0.7457 (3)	0.2315 (4)	0.1292 (19)
H8A	0.2404	0.7104	0.2547	0.194*
H8B	0.1707	0.7832	0.2866	0.194*
H8C	0.1956	0.7875	0.1768	0.194*
C11	0.17380 (15)	0.30216 (17)	0.70816 (19)	0.0391 (5)
C12	0.12238 (18)	0.27311 (19)	0.6177 (2)	0.0520 (7)
H12	0.1214	0.3098	0.5591	0.062*
C13	0.0722 (2)	0.1892 (2)	0.6144 (3)	0.0728 (10)
H13	0.0376	0.1699	0.5536	0.087*
C14	0.0735 (2)	0.1349 (2)	0.7002 (4)	0.0794 (11)
H14	0.0389	0.0794	0.6978	0.095*
C15	0.1253 (2)	0.1616 (2)	0.7894 (3)	0.0686 (10)
H15	0.1267	0.1237	0.8472	0.082*
C16	0.17586 (18)	0.2451 (2)	0.7941 (2)	0.0516 (7)
H16	0.2113	0.2629	0.8550	0.062*
C21	0.23964 (16)	0.47418 (18)	0.82343 (18)	0.0399 (6)
C22	0.1735 (2)	0.4603 (2)	0.8828 (2)	0.0654 (9)
H22	0.1323	0.4106	0.8682	0.078*
C23	0.1694 (3)	0.5217 (3)	0.9650 (3)	0.0909 (13)
H23	0.1250	0.5127	1.0050	0.109*
C24	0.2298 (3)	0.5948 (3)	0.9876 (3)	0.0882 (12)
H24	0.2271	0.6343	1.0434	0.106*
C25	0.2941 (2)	0.6099 (2)	0.9282 (2)	0.0675 (9)
H25	0.3346	0.6603	0.9427	0.081*
C26	0.29900 (18)	0.55016 (19)	0.8468 (2)	0.0483 (6)
H26	0.3430	0.5609	0.8066	0.058*
C31	0.19006 (16)	0.48562 (16)	0.61322 (18)	0.0374 (5)
C32	0.22665 (18)	0.51600 (19)	0.53028 (19)	0.0466 (6)
H32	0.2819	0.4920	0.5198	0.056*
C33	0.1818 (2)	0.5820 (2)	0.4623 (2)	0.0635 (8)
H33	0.2071	0.6015	0.4064	0.076*
C34	0.1014 (2)	0.6185 (2)	0.4766 (3)	0.0709 (9)
H34	0.0721	0.6635	0.4314	0.085*
C35	0.0644 (2)	0.5885 (3)	0.5579 (3)	0.0785 (11)
H35	0.0090	0.6128	0.5675	0.094*
C36	0.10779 (19)	0.5228 (2)	0.6261 (2)	0.0609 (8)
H36	0.0815	0.5032	0.6813	0.073*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ru1	0.03176 (10)	0.02563 (10)	0.02496 (10)	0.00084 (7)	0.00587 (7)	0.00132 (7)
Cl1	0.0517 (4)	0.0445 (3)	0.0275 (3)	0.0104 (3)	0.0035 (2)	−0.0018 (2)
Cl2	0.0371 (3)	0.0440 (3)	0.0454 (3)	0.0047 (3)	0.0098 (3)	0.0021 (3)
P1	0.0319 (3)	0.0319 (3)	0.0300 (3)	0.0012 (2)	0.0053 (2)	0.0004 (2)
N1	0.0382 (11)	0.0327 (11)	0.0341 (10)	0.0009 (8)	0.0092 (8)	0.0015 (9)
N2	0.0377 (11)	0.0326 (11)	0.0291 (10)	0.0022 (8)	0.0074 (8)	0.0001 (8)
N3	0.0336 (10)	0.0278 (10)	0.0306 (10)	−0.0005 (8)	0.0037 (8)	0.0012 (8)
N4	0.119 (3)	0.112 (3)	0.143 (4)	−0.016 (3)	0.032 (3)	−0.026 (3)
C1	0.0415 (13)	0.0381 (13)	0.0330 (12)	−0.0016 (11)	0.0098 (10)	−0.0002 (11)
C2	0.0728 (19)	0.0377 (14)	0.0508 (16)	−0.0087 (13)	0.0116 (14)	0.0101 (12)
C3	0.0416 (13)	0.0354 (13)	0.0379 (13)	0.0009 (11)	0.0090 (10)	−0.0009 (11)
C4	0.072 (2)	0.0343 (14)	0.076 (2)	−0.0049 (14)	0.0177 (16)	0.0093 (14)
C5	0.0438 (14)	0.0269 (11)	0.0365 (14)	−0.0040 (10)	0.0029 (10)	0.0004 (10)
C6	0.091 (2)	0.0459 (15)	0.0293 (13)	−0.0197 (15)	0.0056 (13)	−0.0005 (12)
C7	0.123 (4)	0.072 (3)	0.076 (3)	0.001 (3)	0.019 (3)	−0.005 (2)
C8	0.182 (5)	0.092 (3)	0.104 (4)	−0.038 (4)	−0.009 (3)	−0.002 (3)
C11	0.0309 (12)	0.0373 (13)	0.0499 (14)	0.0019 (10)	0.0092 (10)	0.0027 (11)
C12	0.0465 (15)	0.0428 (15)	0.0629 (18)	0.0015 (12)	−0.0027 (13)	−0.0038 (13)
C13	0.0510 (18)	0.0516 (18)	0.109 (3)	−0.0075 (15)	−0.0077 (18)	−0.020 (2)
C14	0.055 (2)	0.0468 (18)	0.141 (4)	−0.0130 (16)	0.031 (2)	0.000 (2)
C15	0.060 (2)	0.0530 (18)	0.101 (3)	−0.0012 (15)	0.038 (2)	0.0203 (18)
C16	0.0469 (16)	0.0522 (16)	0.0596 (17)	0.0006 (13)	0.0198 (13)	0.0093 (14)
C21	0.0419 (14)	0.0425 (14)	0.0364 (13)	0.0090 (11)	0.0097 (10)	−0.0020 (11)
C22	0.072 (2)	0.068 (2)	0.0646 (19)	−0.0030 (17)	0.0352 (17)	−0.0113 (16)
C23	0.119 (3)	0.095 (3)	0.075 (2)	−0.002 (3)	0.065 (2)	−0.021 (2)
C24	0.121 (3)	0.081 (3)	0.070 (2)	0.001 (2)	0.039 (2)	−0.033 (2)
C25	0.081 (2)	0.0577 (18)	0.065 (2)	0.0018 (17)	0.0141 (17)	−0.0229 (16)
C26	0.0512 (16)	0.0458 (15)	0.0493 (15)	0.0056 (12)	0.0127 (12)	−0.0085 (12)
C31	0.0378 (13)	0.0335 (12)	0.0387 (13)	0.0056 (10)	−0.0003 (10)	0.0023 (10)
C32	0.0465 (15)	0.0497 (15)	0.0435 (14)	0.0150 (12)	0.0067 (11)	0.0074 (12)
C33	0.073 (2)	0.069 (2)	0.0502 (17)	0.0246 (17)	0.0128 (15)	0.0207 (15)
C34	0.069 (2)	0.072 (2)	0.069 (2)	0.0335 (17)	0.0036 (17)	0.0239 (17)
C35	0.0556 (19)	0.097 (3)	0.084 (2)	0.0408 (19)	0.0133 (17)	0.023 (2)
C36	0.0456 (16)	0.074 (2)	0.0648 (19)	0.0170 (15)	0.0137 (14)	0.0158 (16)

Geometric parameters (Å, º)

Ru1—N1	2.0218 (19)	C12—C13	1.389 (4)
Ru1—N2	2.0141 (19)	C12—H12	0.9300
Ru1—N3	2.0044 (18)	C13—C14	1.367 (5)
Ru1—P1	2.2754 (6)	C13—H13	0.9300
Ru1—Cl1	2.4080 (6)	C14—C15	1.365 (5)
Ru1—Cl2	2.5007 (6)	C14—H14	0.9300
P1—C11	1.825 (2)	C15—C16	1.386 (4)
P1—C31	1.838 (2)	C15—H15	0.9300
P1—C21	1.841 (2)	C16—H16	0.9300
N1—C1	1.135 (3)	C21—C22	1.384 (3)
N2—C3	1.135 (3)	C21—C26	1.389 (4)
N3—C5	1.133 (3)	C22—C23	1.398 (4)
N4—C7	1.108 (5)	C22—H22	0.9300
C1—C2	1.450 (3)	C23—C24	1.368 (5)
C2—H2A	0.9600	C23—H23	0.9300
C2—H2B	0.9600	C24—C25	1.363 (5)
C2—H2C	0.9600	C24—H24	0.9300
C3—C4	1.455 (3)	C25—C26	1.377 (4)
C4—H4A	0.9600	C25—H25	0.9300
C4—H4B	0.9600	C26—H26	0.9300
C4—H4C	0.9600	C31—C32	1.379 (3)
C5—C6	1.452 (3)	C31—C36	1.383 (4)
C6—H6A	0.9600	C32—C33	1.387 (4)
C6—H6B	0.9600	C32—H32	0.9300
C6—H6C	0.9600	C33—C34	1.358 (4)
C7—C8	1.434 (6)	C33—H33	0.9300
C8—H8A	0.9600	C34—C35	1.361 (5)
C8—H8B	0.9600	C34—H34	0.9300
C8—H8C	0.9600	C35—C36	1.379 (4)
C11—C12	1.384 (4)	C35—H35	0.9300
C11—C16	1.389 (4)	C36—H36	0.9300
N3—Ru1—N2	87.87 (7)	C12—C11—P1	119.8 (2)
N3—Ru1—N1	94.25 (7)	C16—C11—P1	120.5 (2)
N2—Ru1—N1	176.40 (7)	C11—C12—C13	120.0 (3)
N3—Ru1—P1	90.58 (5)	C11—C12—H12	120.0
N2—Ru1—P1	91.64 (5)	C13—C12—H12	120.0
N1—Ru1—P1	91.26 (5)	C14—C13—C12	120.3 (3)
N3—Ru1—Cl1	175.81 (5)	C14—C13—H13	119.9
N2—Ru1—Cl1	88.02 (5)	C12—C13—H13	119.9
N1—Ru1—Cl1	89.82 (6)	C15—C14—C13	120.3 (3)
P1—Ru1—Cl1	90.31 (2)	C15—C14—H14	119.8
N3—Ru1—Cl2	87.75 (5)	C13—C14—H14	119.8
N2—Ru1—Cl2	89.00 (5)	C14—C15—C16	120.2 (3)
N1—Ru1—Cl2	88.17 (5)	C14—C15—H15	119.9
P1—Ru1—Cl2	178.19 (2)	C16—C15—H15	119.9
Cl1—Ru1—Cl2	91.40 (2)	C15—C16—C11	120.2 (3)
C11—P1—C31	103.47 (11)	C15—C16—H16	119.9
C11—P1—C21	106.07 (11)	C11—C16—H16	119.9
C31—P1—C21	98.27 (11)	C22—C21—C26	118.6 (2)
C11—P1—Ru1	112.66 (8)	C22—C21—P1	124.5 (2)
C31—P1—Ru1	119.79 (8)	C26—C21—P1	116.80 (18)
C21—P1—Ru1	114.73 (8)	C21—C22—C23	119.3 (3)
C1—N1—Ru1	172.6 (2)	C21—C22—H22	120.4
C3—N2—Ru1	179.9 (2)	C23—C22—H22	120.4
C5—N3—Ru1	171.40 (18)	C24—C23—C22	120.9 (3)
N1—C1—C2	176.5 (3)	C24—C23—H23	119.5
C1—C2—H2A	109.5	C22—C23—H23	119.5
C1—C2—H2B	109.5	C25—C24—C23	120.0 (3)
H2A—C2—H2B	109.5	C25—C24—H24	120.0
C1—C2—H2C	109.5	C23—C24—H24	120.0
H2A—C2—H2C	109.5	C24—C25—C26	119.8 (3)
H2B—C2—H2C	109.5	C24—C25—H25	120.1
N2—C3—C4	179.3 (3)	C26—C25—H25	120.1
C3—C4—H4A	109.5	C25—C26—C21	121.4 (3)
C3—C4—H4B	109.5	C25—C26—H26	119.3
H4A—C4—H4B	109.5	C21—C26—H26	119.3
C3—C4—H4C	109.5	C32—C31—C36	118.0 (2)
H4A—C4—H4C	109.5	C32—C31—P1	121.83 (18)
H4B—C4—H4C	109.5	C36—C31—P1	120.1 (2)
N3—C5—C6	176.0 (3)	C31—C32—C33	120.6 (2)
C5—C6—H6A	109.5	C31—C32—H32	119.7
C5—C6—H6B	109.5	C33—C32—H32	119.7
H6A—C6—H6B	109.5	C34—C33—C32	120.7 (3)
C5—C6—H6C	109.5	C34—C33—H33	119.7
H6A—C6—H6C	109.5	C32—C33—H33	119.7
H6B—C6—H6C	109.5	C33—C34—C35	119.2 (3)
N4—C7—C8	178.9 (6)	C33—C34—H34	120.4
C7—C8—H8A	109.5	C35—C34—H34	120.4
C7—C8—H8B	109.5	C34—C35—C36	120.9 (3)
H8A—C8—H8B	109.5	C34—C35—H35	119.5
C7—C8—H8C	109.5	C36—C35—H35	119.5
H8A—C8—H8C	109.5	C35—C36—C31	120.5 (3)
H8B—C8—H8C	109.5	C35—C36—H36	119.7
C12—C11—C16	119.0 (2)	C31—C36—H36	119.7