Tetra­ethyl­ammonium dichloro­tris(2,6-dimethyl­phenyl­sulfanyl-κS)ruthenium dichloro­methane solvate

The title mononuclear ruthenium(IV) complex, (C₈H₂₀N)[Ru(C₈H₉S)₃Cl₂]·CH₂Cl₂, contains the trigonal {Ru(Sxylyl)₃} core (xylyl is 2,6-dimethyl­phen­yl), with S—Ru—S angles in the range 118.07 (6)–123.45 (6)°. The coordination geometry of the central Ru atom is trigonal–bipyramidal, with two Cl atoms in the axial positions. The Ru—S and Ru—Cl bond lengths are 2.1918 (18)–2.2046 (19) and 2.378 (2)–2.385 (2) Å, respectively.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.049
• wR factor = 0.084
• Data-to-parameter ratio = 22.3

checkCIF/PLATON results

No syntax errors found



Alert level C
REFLT03_ALERT_3_C  Reflection count < 95% complete
           From the CIF: _diffrn_reflns_theta_max           28.34
           From the CIF: _diffrn_reflns_theta_full          28.34
           From the CIF: _reflns_number_total               8661
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         9182
           Completeness (_total/calc)             94.33%
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         43 Perc.
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT243_ALERT_4_C High  'Solvent' Ueq as Compared to Neighbors for        C51
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C17

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

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

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Tetraethylammonium dichlorotris(2,6-dimethylphenylsulfanyl-κS)ruthenium dichloromethane solvate

Crystal data

(C8H20N)[Ru(C8H9S)3Cl2]·CH2Cl2	F(000) = 1656
Mr = 798.78	Dx = 1.442 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4257 reflections
a = 13.9279 (10) Å	θ = 2.3–25.0°
b = 12.4525 (16) Å	µ = 0.91 mm^−1
c = 21.2361 (13) Å	T = 293 K
β = 92.162 (18)°	Needle, black
V = 3680.5 (6) Å^3	0.32 × 0.10 × 0.08 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	8661 independent reflections
Radiation source: fine-focus sealed tube	3727 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.067
φ νd ω scans	θmax = 28.3°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −17→7
Tmin = 0.744, Tmax = 0.931	k = −15→16
21935 measured reflections	l = −28→28

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.084	H-atom parameters constrained
S = 0.97	w = 1/[σ^2(Fo^2) + (0.0138P)^2] where P = (Fo^2 + 2Fc^2)/3
8661 reflections	(Δ/σ)max < 0.001
389 parameters	Δρmax = 0.80 e Å^−3
0 restraints	Δρmin = −0.93 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
Ru1	0.30430 (3)	0.22738 (3)	0.866613 (19)	0.01936 (11)
S1	0.19289 (10)	0.19527 (9)	0.79250 (6)	0.0260 (4)
S2	0.26283 (9)	0.22057 (9)	0.96507 (6)	0.0224 (3)
S3	0.45764 (10)	0.24627 (8)	0.84773 (6)	0.0227 (3)
Cl1	0.33709 (10)	0.04018 (8)	0.86172 (6)	0.0275 (4)
Cl2	0.27633 (9)	0.41603 (8)	0.87194 (6)	0.0241 (3)
Cl3	0.19146 (12)	0.60344 (10)	0.03092 (7)	0.0469 (5)
Cl4	0.07514 (12)	0.41416 (11)	0.05528 (8)	0.0562 (5)
N1	0.2466 (3)	0.7378 (3)	0.79831 (18)	0.0191 (10)
C11	0.1254 (4)	0.3092 (4)	0.7649 (2)	0.0232 (13)
C12	0.0584 (4)	0.3592 (4)	0.8035 (3)	0.0294 (14)
C13	0.0068 (4)	0.4457 (4)	0.7795 (3)	0.0320 (15)
H13	−0.0365	0.4806	0.8048	0.038*
C14	0.0184 (4)	0.4810 (4)	0.7190 (3)	0.0388 (16)
H14	−0.0161	0.5401	0.7038	0.047*
C15	0.0809 (4)	0.4289 (4)	0.6811 (3)	0.0365 (16)
H15	0.0861	0.4514	0.6396	0.044*
C16	0.1370 (4)	0.3428 (4)	0.7034 (3)	0.0272 (14)
C17	0.0376 (4)	0.3166 (4)	0.8679 (2)	0.0365 (16)
H17A	−0.0097	0.3613	0.8867	0.055*
H17B	0.0955	0.3169	0.8939	0.055*
H17C	0.0135	0.2446	0.8642	0.055*
C18	0.2033 (4)	0.2883 (4)	0.6592 (2)	0.0391 (16)
H18A	0.2685	0.2964	0.6747	0.059*
H18B	0.1961	0.3203	0.6182	0.059*
H18C	0.1875	0.2133	0.6564	0.059*
C21	0.2655 (4)	0.0876 (3)	0.9965 (2)	0.0189 (13)
C22	0.1819 (4)	0.0233 (4)	0.9881 (2)	0.0236 (13)
C23	0.1844 (4)	−0.0779 (4)	1.0165 (2)	0.0312 (15)
H23	0.1309	−0.1224	1.0121	0.037*
C24	0.2636 (4)	−0.1133 (4)	1.0507 (2)	0.0269 (14)
H24	0.2626	−0.1804	1.0698	0.032*
C25	0.3443 (4)	−0.0507 (4)	1.0570 (2)	0.0287 (14)
H25	0.3978	−0.0763	1.0799	0.034*
C26	0.3473 (4)	0.0514 (3)	1.0293 (2)	0.0204 (13)
C27	0.0965 (4)	0.0596 (4)	0.9492 (2)	0.0344 (15)
H27A	0.0728	0.1257	0.9658	0.052*
H27B	0.0471	0.0059	0.9502	0.052*
H27C	0.1146	0.0704	0.9065	0.052*
C28	0.4351 (4)	0.1176 (4)	1.0360 (2)	0.0317 (15)
H28A	0.4551	0.1386	0.9950	0.048*
H28B	0.4853	0.0767	1.0569	0.048*
H28C	0.4221	0.1805	1.0603	0.048*
C31	0.4976 (3)	0.3822 (3)	0.8446 (2)	0.0186 (12)
C32	0.5367 (4)	0.4302 (3)	0.8990 (2)	0.0232 (13)
C33	0.5748 (3)	0.5325 (4)	0.8943 (2)	0.0248 (13)
H33	0.6009	0.5658	0.9302	0.030*
C34	0.5749 (4)	0.5856 (4)	0.8376 (2)	0.0236 (13)
H34	0.6013	0.6541	0.8353	0.028*
C35	0.5362 (3)	0.5376 (4)	0.7844 (3)	0.0250 (14)
H35	0.5370	0.5741	0.7463	0.030*
C36	0.4955 (4)	0.4353 (4)	0.7860 (2)	0.0226 (13)
C37	0.5383 (4)	0.3734 (3)	0.9611 (2)	0.0308 (15)
H37A	0.4736	0.3584	0.9726	0.046*
H37B	0.5690	0.4181	0.9927	0.046*
H37C	0.5731	0.3072	0.9579	0.046*
C38	0.4507 (4)	0.3854 (3)	0.7278 (2)	0.0280 (14)
H38A	0.4796	0.3166	0.7208	0.042*
H38B	0.4607	0.4312	0.6923	0.042*
H38C	0.3830	0.3764	0.7330	0.042*
C41	0.1657 (4)	0.7959 (3)	0.8279 (2)	0.0254 (14)
H41A	0.1234	0.8240	0.7945	0.031*
H41B	0.1921	0.8567	0.8512	0.031*
C42	0.1057 (4)	0.7297 (4)	0.8722 (2)	0.0372 (15)
H42A	0.0706	0.6761	0.8484	0.056*
H42B	0.0615	0.7759	0.8928	0.056*
H42C	0.1473	0.6955	0.9032	0.056*
C43	0.2070 (4)	0.6484 (3)	0.7568 (2)	0.0298 (14)
H43A	0.1580	0.6781	0.7282	0.036*
H43B	0.1761	0.5961	0.7832	0.036*
C44	0.2808 (4)	0.5911 (4)	0.7185 (2)	0.0368 (16)
H44A	0.3095	0.6412	0.6905	0.055*
H44B	0.2501	0.5346	0.6945	0.055*
H44C	0.3297	0.5610	0.7463	0.055*
C45	0.3134 (4)	0.6896 (3)	0.8474 (2)	0.0258 (14)
H45A	0.3667	0.6573	0.8263	0.031*
H45B	0.2795	0.6322	0.8680	0.031*
C46	0.3540 (4)	0.7642 (4)	0.8978 (2)	0.0307 (13)
H46A	0.3905	0.8199	0.8785	0.046*
H46B	0.3950	0.7245	0.9267	0.046*
H46C	0.3024	0.7957	0.9201	0.046*
C47	0.3016 (4)	0.8170 (3)	0.7599 (2)	0.0257 (14)
H47A	0.3574	0.7808	0.7440	0.031*
H47B	0.3247	0.8740	0.7876	0.031*
C48	0.2465 (4)	0.8670 (4)	0.7050 (2)	0.0380 (16)
H48A	0.2147	0.8118	0.6805	0.057*
H48B	0.2902	0.9051	0.6791	0.057*
H48C	0.1996	0.9161	0.7203	0.057*
C51	0.1599 (5)	0.4737 (4)	0.0093 (3)	0.071 (3)
H51A	0.1354	0.4745	−0.0340	0.086*
H51B	0.2174	0.4296	0.0110	0.086*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ru1	0.0272 (3)	0.01007 (18)	0.0212 (2)	−0.0004 (2)	0.0071 (2)	0.00033 (19)
S1	0.0346 (10)	0.0169 (7)	0.0266 (8)	−0.0037 (6)	0.0037 (7)	−0.0010 (5)
S2	0.0297 (9)	0.0146 (6)	0.0235 (7)	−0.0007 (6)	0.0084 (6)	0.0001 (6)
S3	0.0303 (9)	0.0099 (7)	0.0286 (8)	0.0008 (5)	0.0093 (7)	−0.0005 (5)
Cl1	0.0436 (10)	0.0111 (6)	0.0288 (8)	−0.0001 (6)	0.0137 (7)	0.0001 (5)
Cl2	0.0280 (9)	0.0113 (6)	0.0337 (8)	0.0012 (5)	0.0092 (7)	0.0006 (5)
Cl3	0.0601 (13)	0.0329 (8)	0.0479 (11)	−0.0083 (8)	0.0028 (9)	−0.0097 (7)
Cl4	0.0613 (13)	0.0410 (9)	0.0684 (13)	0.0044 (9)	0.0298 (11)	0.0197 (8)
N1	0.021 (3)	0.011 (2)	0.026 (2)	−0.0015 (19)	0.003 (2)	0.0016 (18)
C11	0.020 (4)	0.025 (3)	0.024 (3)	−0.007 (2)	−0.010 (3)	0.001 (2)
C12	0.021 (4)	0.027 (3)	0.040 (4)	−0.004 (3)	−0.005 (3)	0.001 (3)
C13	0.023 (4)	0.025 (3)	0.048 (4)	−0.004 (3)	−0.002 (3)	−0.003 (3)
C14	0.032 (4)	0.023 (3)	0.060 (5)	−0.008 (3)	−0.015 (4)	0.005 (3)
C15	0.037 (4)	0.037 (3)	0.034 (4)	−0.014 (3)	−0.013 (3)	0.011 (3)
C16	0.029 (4)	0.023 (3)	0.029 (3)	−0.011 (3)	−0.011 (3)	−0.002 (2)
C17	0.042 (4)	0.032 (3)	0.037 (4)	0.007 (3)	0.011 (3)	0.002 (3)
C18	0.047 (4)	0.042 (3)	0.028 (3)	−0.013 (3)	−0.003 (3)	0.002 (3)
C21	0.026 (4)	0.013 (2)	0.018 (3)	−0.001 (2)	0.012 (3)	−0.003 (2)
C22	0.028 (4)	0.023 (3)	0.021 (3)	−0.006 (3)	0.008 (3)	0.001 (2)
C23	0.044 (4)	0.020 (3)	0.031 (4)	−0.015 (3)	0.017 (3)	−0.003 (3)
C24	0.044 (4)	0.014 (3)	0.023 (3)	−0.004 (3)	0.004 (3)	0.002 (2)
C25	0.043 (4)	0.018 (3)	0.026 (3)	0.005 (3)	0.008 (3)	0.003 (2)
C26	0.029 (4)	0.016 (3)	0.017 (3)	0.002 (2)	0.008 (3)	0.000 (2)
C27	0.031 (4)	0.038 (3)	0.034 (4)	−0.017 (3)	0.001 (3)	0.009 (3)
C28	0.031 (4)	0.026 (3)	0.038 (4)	−0.005 (3)	−0.001 (3)	0.000 (3)
C31	0.017 (3)	0.011 (2)	0.029 (3)	0.000 (2)	0.006 (3)	0.000 (2)
C32	0.032 (4)	0.014 (2)	0.024 (3)	0.003 (2)	0.013 (3)	0.003 (2)
C33	0.026 (4)	0.022 (3)	0.027 (3)	−0.002 (2)	0.007 (3)	−0.004 (2)
C34	0.026 (4)	0.012 (2)	0.032 (4)	−0.006 (2)	0.005 (3)	−0.002 (2)
C35	0.019 (3)	0.022 (3)	0.035 (4)	−0.003 (3)	0.013 (3)	0.011 (3)
C36	0.020 (3)	0.019 (3)	0.029 (3)	0.005 (2)	0.007 (3)	−0.002 (2)
C37	0.048 (4)	0.022 (3)	0.022 (3)	0.004 (3)	0.000 (3)	0.000 (2)
C38	0.033 (4)	0.021 (3)	0.030 (3)	−0.001 (3)	0.006 (3)	0.005 (2)
C41	0.027 (4)	0.021 (3)	0.029 (3)	0.009 (2)	0.008 (3)	0.001 (2)
C42	0.031 (4)	0.041 (3)	0.041 (4)	0.001 (3)	0.017 (3)	0.007 (3)
C43	0.030 (4)	0.023 (3)	0.036 (4)	−0.009 (3)	−0.003 (3)	−0.003 (2)
C44	0.045 (4)	0.029 (3)	0.037 (4)	−0.006 (3)	0.007 (3)	−0.015 (3)
C45	0.023 (4)	0.015 (2)	0.039 (4)	0.005 (2)	0.009 (3)	0.005 (2)
C46	0.036 (4)	0.029 (3)	0.027 (3)	−0.002 (3)	−0.004 (3)	0.003 (3)
C47	0.027 (4)	0.021 (3)	0.030 (3)	−0.003 (2)	0.009 (3)	0.000 (2)
C48	0.036 (4)	0.044 (3)	0.034 (4)	0.000 (3)	0.005 (3)	0.022 (3)
C51	0.084 (6)	0.036 (4)	0.099 (6)	−0.014 (4)	0.064 (5)	−0.017 (4)

Geometric parameters (Å, º)

Ru1—S2	2.1918 (18)	C28—H28B	0.9600
Ru1—S3	2.201 (2)	C28—H28C	0.9600
Ru1—S1	2.2046 (19)	C31—C32	1.394 (7)
Ru1—Cl1	2.378 (2)	C31—C36	1.408 (6)
Ru1—Cl2	2.385 (2)	C32—C33	1.385 (6)
S1—C11	1.789 (5)	C32—C37	1.497 (6)
S2—C21	1.785 (5)	C33—C34	1.373 (6)
S3—C31	1.784 (4)	C33—H33	0.9300
Cl3—C51	1.732 (5)	C34—C35	1.371 (6)
Cl4—C51	1.727 (5)	C34—H34	0.9300
N1—C45	1.496 (6)	C35—C36	1.395 (6)
N1—C41	1.498 (5)	C35—H35	0.9300
N1—C47	1.507 (5)	C36—C38	1.499 (7)
N1—C43	1.511 (6)	C37—H37A	0.9600
C11—C16	1.387 (6)	C37—H37B	0.9600
C11—C12	1.410 (6)	C37—H37C	0.9600
C12—C13	1.382 (7)	C38—H38A	0.9600
C12—C17	1.505 (7)	C38—H38B	0.9600
C13—C14	1.373 (7)	C38—H38C	0.9600
C13—H13	0.9300	C41—C42	1.522 (6)
C14—C15	1.371 (7)	C41—H41A	0.9700
C14—H14	0.9300	C41—H41B	0.9700
C15—C16	1.399 (7)	C42—H42A	0.9600
C15—H15	0.9300	C42—H42B	0.9600
C16—C18	1.503 (6)	C42—H42C	0.9600
C17—H17A	0.9600	C43—C44	1.514 (6)
C17—H17B	0.9600	C43—H43A	0.9700
C17—H17C	0.9600	C43—H43B	0.9700
C18—H18A	0.9600	C44—H44A	0.9600
C18—H18B	0.9600	C44—H44B	0.9600
C18—H18C	0.9600	C44—H44C	0.9600
C21—C26	1.388 (7)	C45—C46	1.511 (6)
C21—C22	1.418 (7)	C45—H45A	0.9700
C22—C23	1.397 (6)	C45—H45B	0.9700
C22—C27	1.493 (7)	C46—H46A	0.9600
C23—C24	1.370 (7)	C46—H46B	0.9600
C23—H23	0.9300	C46—H46C	0.9600
C24—C25	1.370 (7)	C47—C48	1.507 (7)
C24—H24	0.9300	C47—H47A	0.9700
C25—C26	1.401 (6)	C47—H47B	0.9700
C25—H25	0.9300	C48—H48A	0.9600
C26—C28	1.478 (6)	C48—H48B	0.9600
C27—H27A	0.9600	C48—H48C	0.9600
C27—H27B	0.9600	C51—H51A	0.9700
C27—H27C	0.9600	C51—H51B	0.9700
C28—H28A	0.9600
S2—Ru1—S3	118.07 (6)	C33—C32—C31	118.3 (4)
S2—Ru1—S1	118.05 (7)	C33—C32—C37	120.4 (5)
S3—Ru1—S1	123.45 (6)	C31—C32—C37	121.3 (4)
S2—Ru1—Cl1	93.54 (5)	C34—C33—C32	121.3 (5)
S3—Ru1—Cl1	84.70 (5)	C34—C33—H33	119.3
S1—Ru1—Cl1	85.54 (5)	C32—C33—H33	119.3
S2—Ru1—Cl2	86.76 (4)	C35—C34—C33	119.9 (5)
S3—Ru1—Cl2	93.71 (5)	C35—C34—H34	120.1
S1—Ru1—Cl2	95.78 (5)	C33—C34—H34	120.1
Cl1—Ru1—Cl2	178.33 (5)	C34—C35—C36	121.8 (5)
C11—S1—Ru1	115.95 (17)	C34—C35—H35	119.1
C21—S2—Ru1	112.97 (15)	C36—C35—H35	119.1
C31—S3—Ru1	114.52 (16)	C35—C36—C31	117.1 (5)
C45—N1—C41	111.0 (4)	C35—C36—C38	121.1 (5)
C45—N1—C47	109.0 (4)	C31—C36—C38	121.9 (4)
C41—N1—C47	108.5 (3)	C32—C37—H37A	109.5
C45—N1—C43	108.4 (4)	C32—C37—H37B	109.5
C41—N1—C43	109.6 (4)	H37A—C37—H37B	109.5
C47—N1—C43	110.4 (4)	C32—C37—H37C	109.5
C16—C11—C12	121.2 (5)	H37A—C37—H37C	109.5
C16—C11—S1	118.0 (4)	H37B—C37—H37C	109.5
C12—C11—S1	120.7 (4)	C36—C38—H38A	109.5
C13—C12—C11	118.4 (5)	C36—C38—H38B	109.5
C13—C12—C17	119.6 (5)	H38A—C38—H38B	109.5
C11—C12—C17	121.8 (5)	C36—C38—H38C	109.5
C14—C13—C12	121.1 (5)	H38A—C38—H38C	109.5
C14—C13—H13	119.4	H38B—C38—H38C	109.5
C12—C13—H13	119.4	N1—C41—C42	115.9 (4)
C15—C14—C13	119.9 (6)	N1—C41—H41A	108.3
C15—C14—H14	120.1	C42—C41—H41A	108.3
C13—C14—H14	120.1	N1—C41—H41B	108.3
C14—C15—C16	121.5 (5)	C42—C41—H41B	108.3
C14—C15—H15	119.3	H41A—C41—H41B	107.4
C16—C15—H15	119.3	C41—C42—H42A	109.5
C11—C16—C15	117.8 (5)	C41—C42—H42B	109.5
C11—C16—C18	123.3 (5)	H42A—C42—H42B	109.5
C15—C16—C18	118.9 (5)	C41—C42—H42C	109.5
C12—C17—H17A	109.5	H42A—C42—H42C	109.5
C12—C17—H17B	109.5	H42B—C42—H42C	109.5
H17A—C17—H17B	109.5	N1—C43—C44	114.8 (4)
C12—C17—H17C	109.5	N1—C43—H43A	108.6
H17A—C17—H17C	109.5	C44—C43—H43A	108.6
H17B—C17—H17C	109.5	N1—C43—H43B	108.6
C16—C18—H18A	109.5	C44—C43—H43B	108.6
C16—C18—H18B	109.5	H43A—C43—H43B	107.5
H18A—C18—H18B	109.5	C43—C44—H44A	109.5
C16—C18—H18C	109.5	C43—C44—H44B	109.5
H18A—C18—H18C	109.5	H44A—C44—H44B	109.5
H18B—C18—H18C	109.5	C43—C44—H44C	109.5
C26—C21—C22	122.2 (4)	H44A—C44—H44C	109.5
C26—C21—S2	119.6 (4)	H44B—C44—H44C	109.5
C22—C21—S2	118.1 (4)	N1—C45—C46	116.9 (4)
C23—C22—C21	116.6 (5)	N1—C45—H45A	108.1
C23—C22—C27	121.2 (5)	C46—C45—H45A	108.1
C21—C22—C27	122.1 (4)	N1—C45—H45B	108.1
C24—C23—C22	121.6 (5)	C46—C45—H45B	108.1
C24—C23—H23	119.2	H45A—C45—H45B	107.3
C22—C23—H23	119.2	C45—C46—H46A	109.5
C25—C24—C23	120.7 (5)	C45—C46—H46B	109.5
C25—C24—H24	119.7	H46A—C46—H46B	109.5
C23—C24—H24	119.7	C45—C46—H46C	109.5
C24—C25—C26	120.8 (5)	H46A—C46—H46C	109.5
C24—C25—H25	119.6	H46B—C46—H46C	109.5
C26—C25—H25	119.6	N1—C47—C48	115.8 (4)
C21—C26—C25	117.9 (5)	N1—C47—H47A	108.3
C21—C26—C28	121.8 (4)	C48—C47—H47A	108.3
C25—C26—C28	120.2 (5)	N1—C47—H47B	108.3
C22—C27—H27A	109.5	C48—C47—H47B	108.3
C22—C27—H27B	109.5	H47A—C47—H47B	107.4
H27A—C27—H27B	109.5	C47—C48—H48A	109.5
C22—C27—H27C	109.5	C47—C48—H48B	109.5
H27A—C27—H27C	109.5	H48A—C48—H48B	109.5
H27B—C27—H27C	109.5	C47—C48—H48C	109.5
C26—C28—H28A	109.5	H48A—C48—H48C	109.5
C26—C28—H28B	109.5	H48B—C48—H48C	109.5
H28A—C28—H28B	109.5	Cl4—C51—Cl3	115.0 (3)
C26—C28—H28C	109.5	Cl4—C51—H51A	108.5
H28A—C28—H28C	109.5	Cl3—C51—H51A	108.5
H28B—C28—H28C	109.5	Cl4—C51—H51B	108.5
C32—C31—C36	121.7 (4)	Cl3—C51—H51B	108.5
C32—C31—S3	119.3 (4)	H51A—C51—H51B	107.5
C36—C31—S3	118.9 (4)