4,6-Di­chloro-2-(methyl­thio)­pyrimidine

The structure of the title compound, C₃₀H₂₄Cl₁₂N₁₂S₆, (I), comprises six symmetry unique mol­ecules that vary only slightly in their N-C-S-C torsion angle. All the mol­ecules are planar to within less than 3.1°.

Computing details

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97.

'4,6-Dichloro-2-methylthiopyrimidine'

Crystal data

C5H4Cl2N2S	F(000) = 1176
Mr = 195.07	Dx = 1.666 Mg m^−3
Triclinic, P1	Melting point: 305 - 311 K K
a = 13.6482 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 14.1294 (2) Å	Cell parameters from 15842 reflections
c = 14.1343 (2) Å	θ = 2.9–27.5°
α = 119.9578 (7)°	µ = 1.02 mm^−1
β = 95.9391 (6)°	T = 150 K
γ = 92.8349 (7)°	Block, yellow
V = 2332.60 (6) Å^3	0.30 × 0.13 × 0.13 mm
Z = 12

Data collection

Enraf Nonius KappaCCD area-detector diffractometer	10671 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode	8028 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 2.9°
φ and ω scans	h = −17→17
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −18→18
Tmin = 0.749, Tmax = 0.883	l = −18→18
34427 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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.099	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0491P)^2 + 0.2046P] where P = (Fo^2 + 2Fc^2)/3
10671 reflections	(Δ/σ)max = 0.029
547 parameters	Δρmax = 0.47 e Å^−3
0 restraints	Δρmin = −0.47 e Å^−3

Special details

Experimental. PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range.

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

	x	y	z	Uiso*/Ueq
N1A	0.38534 (10)	0.20309 (12)	0.45142 (12)	0.0238 (3)
C2A	0.39314 (12)	0.23552 (15)	0.37786 (15)	0.0232 (4)
S21A	0.39650 (4)	0.37482 (4)	0.41972 (4)	0.02945 (12)
C22A	0.38244 (14)	0.43636 (16)	0.56270 (16)	0.0337 (5)
H21A	0.3199	0.4044	0.5692	0.042*
H22A	0.3818	0.5159	0.5948	0.042*
H23A	0.4379	0.4224	0.6022	0.042*
N3A	0.39832 (11)	0.17091 (13)	0.26982 (13)	0.0263 (4)
C4A	0.39408 (13)	0.06466 (16)	0.23484 (15)	0.0256 (4)
Cl4A	0.39692 (4)	−0.02227 (4)	0.09511 (4)	0.03840 (13)
C5A	0.38798 (13)	0.01918 (16)	0.30139 (15)	0.0261 (4)
H5A	0.3869	−0.0574	0.2745	0.033*
C6A	0.38369 (12)	0.09512 (16)	0.40987 (15)	0.0241 (4)
Cl6A	0.37358 (4)	0.04948 (4)	0.50201 (4)	0.03126 (12)
N1B	0.37395 (10)	−0.64194 (13)	−0.05875 (12)	0.0240 (3)
C2B	0.36984 (12)	−0.56773 (16)	0.04714 (15)	0.0247 (4)
S21B	0.36834 (4)	−0.60995 (5)	0.14405 (4)	0.03389 (13)
C22B	0.37360 (15)	−0.75550 (17)	0.06153 (17)	0.0358 (5)
H21B	0.3144	−0.7894	0.0054	0.045*
H22B	0.3762	−0.7878	0.1089	0.045*
H23B	0.4330	−0.7686	0.0253	0.045*
N3B	0.36811 (11)	−0.45863 (13)	0.09106 (12)	0.0265 (4)
C4B	0.37426 (13)	−0.42366 (16)	0.02107 (15)	0.0252 (4)
Cl4B	0.37424 (4)	−0.28314 (4)	0.07432 (4)	0.03737 (13)
C5B	0.38106 (12)	−0.48975 (16)	−0.08984 (15)	0.0259 (4)
H5B	0.3862	−0.4618	−0.1381	0.032*
C6B	0.37965 (12)	−0.59970 (16)	−0.12390 (14)	0.0240 (4)
Cl6B	0.38529 (4)	−0.69211 (4)	−0.26081 (4)	0.03322 (12)
N1C	0.36536 (10)	−0.13544 (13)	0.60558 (12)	0.0244 (3)
C2C	0.36130 (12)	−0.24285 (16)	0.57346 (15)	0.0244 (4)
S21C	0.35783 (4)	−0.34074 (4)	0.43411 (4)	0.03170 (13)
C22C	0.36817 (15)	−0.25618 (18)	0.37330 (16)	0.0357 (5)
H21C	0.3135	−0.2105	0.3891	0.045*
H22C	0.3651	−0.3031	0.2932	0.045*
H23C	0.4316	−0.2088	0.4043	0.045*
N3C	0.35872 (10)	−0.28674 (13)	0.63869 (13)	0.0258 (3)
C4C	0.35788 (12)	−0.21496 (16)	0.74394 (15)	0.0248 (4)
Cl4C	0.35552 (4)	−0.26781 (4)	0.83095 (4)	0.03655 (13)
C5C	0.35842 (13)	−0.10257 (16)	0.78816 (15)	0.0267 (4)
H5C	0.3560	−0.0530	0.8641	0.033*
C6C	0.36282 (13)	−0.06935 (15)	0.71234 (15)	0.0245 (4)
Cl6C	0.36721 (4)	0.06942 (4)	0.75702 (4)	0.03605 (13)
N1D	−0.13026 (10)	0.57481 (13)	0.10062 (12)	0.0238 (3)
C2D	−0.12170 (12)	0.60705 (16)	0.02722 (15)	0.0245 (4)
S21D	−0.11406 (4)	0.74656 (4)	0.06969 (4)	0.03232 (13)
C22D	−0.12531 (15)	0.80767 (17)	0.21327 (17)	0.0377 (5)
H21D	−0.1892	0.7793	0.2209	0.047*
H22D	−0.1216	0.8877	0.2469	0.047*
H23D	−0.0713	0.7894	0.2505	0.047*
N3D	−0.11544 (11)	0.54151 (14)	−0.08108 (13)	0.0265 (4)
C4D	−0.11707 (12)	0.43629 (16)	−0.11474 (14)	0.0249 (4)
Cl4D	−0.10867 (4)	0.34975 (4)	−0.25278 (4)	0.03609 (13)
C5D	−0.12364 (12)	0.39137 (16)	−0.04771 (15)	0.0250 (4)
H5D	−0.1238	0.3150	−0.0740	0.031*
C6D	−0.12989 (12)	0.46759 (16)	0.06058 (15)	0.0240 (4)
Cl6D	−0.13668 (4)	0.42284 (4)	0.15354 (4)	0.03442 (13)
N1E	−0.13631 (10)	−0.26910 (13)	−0.40530 (12)	0.0245 (3)
C2E	−0.14368 (12)	−0.19540 (16)	−0.30031 (14)	0.0230 (4)
S21E	−0.14966 (4)	−0.23771 (4)	−0.20408 (4)	0.03033 (12)
C22E	−0.13719 (15)	−0.38207 (17)	−0.28445 (17)	0.0351 (5)
H21E	−0.1920	−0.4185	−0.3459	0.044*
H22E	−0.1387	−0.4148	−0.2376	0.044*
H23E	−0.0740	−0.3915	−0.3136	0.044*
N3E	−0.14731 (11)	−0.08639 (13)	−0.25718 (12)	0.0261 (4)
C4E	−0.14168 (13)	−0.05132 (16)	−0.32751 (16)	0.0262 (4)
Cl4E	−0.14325 (4)	0.08865 (4)	−0.27476 (4)	0.03697 (13)
C5E	−0.13493 (13)	−0.11798 (16)	−0.43852 (15)	0.0266 (4)
H5E	−0.1320	−0.0907	−0.4876	0.033*
C6E	−0.13288 (13)	−0.22724 (16)	−0.47106 (14)	0.0237 (4)
Cl6E	−0.12455 (4)	−0.31956 (4)	−0.60781 (4)	0.03154 (12)
N1F	−0.11133 (10)	1.24180 (13)	0.26273 (12)	0.0245 (3)
C2F	−0.10841 (13)	1.13584 (16)	0.23193 (15)	0.0248 (4)
S21F	−0.10814 (4)	1.03782 (4)	0.09317 (4)	0.03462 (13)
C22F	−0.11303 (15)	1.12010 (18)	0.02900 (16)	0.0365 (5)
H21F	−0.1713	1.1603	0.0461	0.046*
H22F	−0.1177	1.0723	−0.0512	0.046*
H23F	−0.0528	1.1725	0.0571	0.046*
N3F	−0.10731 (11)	1.09240 (13)	0.29836 (13)	0.0267 (4)
C4F	−0.11196 (13)	1.16331 (16)	0.40246 (16)	0.0258 (4)
Cl4F	−0.11438 (4)	1.11032 (5)	0.48962 (4)	0.03747 (13)
C5F	−0.11586 (13)	1.27476 (16)	0.44580 (15)	0.0254 (4)
H5F	−0.1186	1.3241	0.5217	0.032*
C6F	−0.11542 (12)	1.30811 (15)	0.36917 (15)	0.0239 (4)
Cl6F	−0.12257 (4)	1.44450 (4)	0.41160 (4)	0.03168 (12)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0251 (8)	0.0201 (9)	0.0270 (8)	0.0024 (6)	0.0041 (6)	0.0126 (7)
C2A	0.0194 (9)	0.0224 (10)	0.0297 (10)	0.0035 (7)	0.0037 (7)	0.0146 (9)
S21A	0.0365 (3)	0.0213 (3)	0.0351 (3)	0.0040 (2)	0.0074 (2)	0.0172 (2)
C22A	0.0405 (11)	0.0214 (11)	0.0359 (12)	0.0054 (8)	0.0108 (9)	0.0111 (9)
N3A	0.0273 (8)	0.0264 (10)	0.0270 (9)	0.0024 (7)	0.0036 (6)	0.0150 (8)
C4A	0.0253 (9)	0.0276 (11)	0.0210 (9)	0.0030 (8)	0.0023 (7)	0.0104 (9)
Cl4A	0.0549 (3)	0.0325 (3)	0.0210 (3)	0.0026 (2)	0.0046 (2)	0.0090 (2)
C5A	0.0313 (10)	0.0184 (10)	0.0284 (10)	0.0036 (8)	0.0052 (8)	0.0115 (9)
C6A	0.0234 (9)	0.0252 (11)	0.0272 (10)	0.0025 (7)	0.0035 (7)	0.0159 (9)
Cl6A	0.0453 (3)	0.0261 (3)	0.0281 (3)	0.0051 (2)	0.0070 (2)	0.0177 (2)
N1B	0.0259 (8)	0.0231 (9)	0.0247 (8)	0.0038 (6)	0.0050 (6)	0.0131 (7)
C2B	0.0226 (9)	0.0298 (11)	0.0232 (10)	0.0038 (7)	0.0042 (7)	0.0145 (9)
S21B	0.0459 (3)	0.0367 (3)	0.0258 (3)	0.0084 (2)	0.0088 (2)	0.0199 (2)
C22B	0.0464 (12)	0.0361 (13)	0.0365 (12)	0.0099 (10)	0.0077 (9)	0.0261 (11)
N3B	0.0287 (8)	0.0256 (9)	0.0239 (8)	0.0028 (7)	0.0034 (6)	0.0118 (7)
C4B	0.0241 (9)	0.0211 (10)	0.0285 (10)	0.0021 (7)	0.0036 (7)	0.0113 (9)
Cl4B	0.0513 (3)	0.0205 (3)	0.0366 (3)	0.0035 (2)	0.0083 (2)	0.0115 (2)
C5B	0.0286 (10)	0.0249 (11)	0.0298 (10)	0.0026 (8)	0.0056 (8)	0.0179 (9)
C6B	0.0243 (9)	0.0255 (11)	0.0208 (9)	0.0034 (7)	0.0030 (7)	0.0107 (8)
Cl6B	0.0492 (3)	0.0269 (3)	0.0228 (2)	0.0067 (2)	0.0106 (2)	0.0110 (2)
N1C	0.0257 (8)	0.0230 (9)	0.0249 (8)	0.0045 (6)	0.0047 (6)	0.0122 (7)
C2C	0.0197 (9)	0.0259 (11)	0.0266 (10)	0.0038 (7)	0.0040 (7)	0.0123 (9)
S21C	0.0383 (3)	0.0243 (3)	0.0245 (3)	0.0034 (2)	0.0042 (2)	0.0066 (2)
C22C	0.0402 (11)	0.0372 (13)	0.0232 (10)	0.0008 (9)	0.0051 (8)	0.0108 (10)
N3C	0.0236 (8)	0.0247 (9)	0.0292 (9)	0.0026 (6)	0.0036 (6)	0.0140 (8)
C4C	0.0231 (9)	0.0282 (11)	0.0301 (11)	0.0033 (8)	0.0037 (7)	0.0199 (9)
Cl4C	0.0475 (3)	0.0368 (3)	0.0366 (3)	0.0055 (2)	0.0067 (2)	0.0268 (3)
C5C	0.0295 (10)	0.0279 (11)	0.0237 (10)	0.0066 (8)	0.0076 (7)	0.0128 (9)
C6C	0.0275 (9)	0.0203 (10)	0.0265 (10)	0.0068 (7)	0.0056 (7)	0.0118 (9)
Cl6C	0.0580 (3)	0.0212 (3)	0.0310 (3)	0.0112 (2)	0.0109 (2)	0.0135 (2)
N1D	0.0251 (8)	0.0225 (9)	0.0248 (8)	0.0027 (6)	0.0046 (6)	0.0125 (7)
C2D	0.0203 (9)	0.0254 (11)	0.0303 (10)	0.0025 (7)	0.0037 (7)	0.0161 (9)
S21D	0.0389 (3)	0.0245 (3)	0.0385 (3)	0.0032 (2)	0.0065 (2)	0.0195 (2)
C22D	0.0438 (12)	0.0229 (11)	0.0413 (13)	0.0042 (9)	0.0093 (9)	0.0119 (10)
N3D	0.0251 (8)	0.0301 (10)	0.0280 (9)	0.0029 (7)	0.0034 (6)	0.0175 (8)
C4D	0.0228 (9)	0.0291 (11)	0.0217 (10)	0.0038 (8)	0.0037 (7)	0.0120 (9)
Cl4D	0.0454 (3)	0.0366 (3)	0.0208 (2)	0.0052 (2)	0.0049 (2)	0.0105 (2)
C5D	0.0268 (9)	0.0215 (10)	0.0263 (10)	0.0039 (7)	0.0043 (7)	0.0116 (9)
C6D	0.0241 (9)	0.0263 (11)	0.0254 (10)	0.0023 (7)	0.0029 (7)	0.0160 (9)
Cl6D	0.0536 (3)	0.0286 (3)	0.0275 (3)	0.0057 (2)	0.0082 (2)	0.0185 (2)
N1E	0.0243 (8)	0.0267 (9)	0.0249 (8)	0.0026 (6)	0.0043 (6)	0.0147 (7)
C2E	0.0218 (9)	0.0281 (11)	0.0219 (9)	0.0021 (7)	0.0023 (7)	0.0150 (9)
S21E	0.0379 (3)	0.0350 (3)	0.0241 (3)	0.0066 (2)	0.0078 (2)	0.0187 (2)
C22E	0.0452 (12)	0.0349 (13)	0.0373 (12)	0.0103 (9)	0.0108 (9)	0.0259 (11)
N3E	0.0260 (8)	0.0268 (9)	0.0247 (8)	0.0026 (6)	0.0040 (6)	0.0125 (7)
C4E	0.0253 (9)	0.0216 (10)	0.0303 (10)	0.0019 (7)	0.0036 (7)	0.0124 (9)
Cl4E	0.0495 (3)	0.0198 (3)	0.0370 (3)	0.0008 (2)	0.0062 (2)	0.0113 (2)
C5E	0.0298 (10)	0.0275 (11)	0.0270 (10)	0.0030 (8)	0.0047 (8)	0.0171 (9)
C6E	0.0244 (9)	0.0268 (11)	0.0218 (9)	0.0046 (7)	0.0049 (7)	0.0133 (9)
Cl6E	0.0466 (3)	0.0270 (3)	0.0206 (2)	0.0059 (2)	0.00906 (19)	0.0110 (2)
N1F	0.0264 (8)	0.0258 (9)	0.0212 (8)	0.0046 (6)	0.0037 (6)	0.0115 (7)
C2F	0.0249 (9)	0.0231 (11)	0.0240 (10)	0.0026 (7)	0.0044 (7)	0.0100 (9)
S21F	0.0483 (3)	0.0251 (3)	0.0237 (3)	0.0072 (2)	0.0071 (2)	0.0068 (2)
C22F	0.0489 (12)	0.0372 (13)	0.0218 (10)	0.0085 (10)	0.0055 (9)	0.0133 (10)
N3F	0.0306 (8)	0.0233 (9)	0.0262 (9)	0.0043 (7)	0.0057 (6)	0.0122 (8)
C4F	0.0222 (9)	0.0298 (11)	0.0301 (10)	0.0030 (8)	0.0039 (7)	0.0186 (9)
Cl4F	0.0512 (3)	0.0373 (3)	0.0361 (3)	0.0072 (2)	0.0118 (2)	0.0265 (3)
C5F	0.0281 (10)	0.0291 (11)	0.0187 (9)	0.0063 (8)	0.0061 (7)	0.0111 (9)
C6F	0.0211 (9)	0.0221 (10)	0.0268 (10)	0.0030 (7)	0.0033 (7)	0.0111 (9)
Cl6F	0.0445 (3)	0.0219 (3)	0.0284 (3)	0.0073 (2)	0.0063 (2)	0.0122 (2)

Geometric parameters (Å, º)

N1A—C6A	1.331 (2)	N1D—C6D	1.327 (2)
N1A—C2A	1.340 (2)	N1D—C2D	1.338 (2)
C2A—N3A	1.344 (2)	C2D—N3D	1.352 (2)
C2A—S21A	1.7460 (19)	C2D—S21D	1.744 (2)
S21A—C22A	1.794 (2)	S21D—C22D	1.793 (2)
C22A—H21A	0.9800	C22D—H21D	0.9800
C22A—H22A	0.9800	C22D—H22D	0.9800
C22A—H23A	0.9800	C22D—H23D	0.9800
N3A—C4A	1.321 (2)	N3D—C4D	1.313 (3)
C4A—C5A	1.385 (3)	C4D—C5D	1.386 (3)
C4A—Cl4A	1.7345 (18)	C4D—Cl4D	1.7298 (18)
C5A—C6A	1.374 (3)	C5D—C6D	1.378 (3)
C5A—H5A	0.9500	C5D—H5D	0.9500
C6A—Cl6A	1.7315 (18)	C6D—Cl6D	1.7274 (18)
N1B—C6B	1.330 (2)	N1E—C6E	1.331 (2)
N1B—C2B	1.341 (2)	N1E—C2E	1.340 (2)
C2B—N3B	1.347 (2)	C2E—N3E	1.350 (2)
C2B—S21B	1.7472 (19)	C2E—S21E	1.7447 (18)
S21B—C22B	1.798 (2)	S21E—C22E	1.800 (2)
C22B—H21B	0.9800	C22E—H21E	0.9800
C22B—H22B	0.9800	C22E—H22E	0.9800
C22B—H23B	0.9800	C22E—H23E	0.9800
N3B—C4B	1.316 (2)	N3E—C4E	1.320 (2)
C4B—C5B	1.384 (3)	C4E—C5E	1.386 (3)
C4B—Cl4B	1.7366 (19)	C4E—Cl4E	1.733 (2)
C5B—C6B	1.376 (3)	C5E—C6E	1.376 (3)
C5B—H5B	0.9500	C5E—H5E	0.9500
C6B—Cl6B	1.7243 (18)	C6E—Cl6E	1.7299 (18)
N1C—C6C	1.326 (2)	N1F—C6F	1.326 (2)
N1C—C2C	1.346 (2)	N1F—C2F	1.338 (2)
C2C—N3C	1.346 (2)	C2F—N3F	1.354 (2)
C2C—S21C	1.7459 (19)	C2F—S21F	1.7475 (18)
S21C—C22C	1.794 (2)	S21F—C22F	1.796 (2)
C22C—H21C	0.9800	C22F—H21F	0.9800
C22C—H22C	0.9800	C22F—H22F	0.9800
C22C—H23C	0.9800	C22F—H23F	0.9800
N3C—C4C	1.319 (2)	N3F—C4F	1.314 (2)
C4C—C5C	1.385 (3)	C4F—C5F	1.382 (3)
C4C—Cl4C	1.7304 (18)	C4F—Cl4F	1.7340 (19)
C5C—C6C	1.373 (3)	C5F—C6F	1.381 (3)
C5C—H5C	0.9500	C5F—H5F	0.9500
C6C—Cl6C	1.7294 (19)	C6F—Cl6F	1.7203 (19)
C6A—N1A—C2A	114.36 (16)	C6D—N1D—C2D	114.73 (16)
N1A—C2A—N3A	126.83 (17)	N1D—C2D—N3D	126.51 (18)
N1A—C2A—S21A	119.86 (14)	N1D—C2D—S21D	119.88 (14)
N3A—C2A—S21A	113.31 (14)	N3D—C2D—S21D	113.59 (14)
C2A—S21A—C22A	102.43 (9)	C2D—S21D—C22D	101.92 (10)
S21A—C22A—H21A	109.5	S21D—C22D—H21D	109.5
S21A—C22A—H22A	109.5	S21D—C22D—H22D	109.5
H21A—C22A—H22A	109.5	H21D—C22D—H22D	109.5
S21A—C22A—H23A	109.5	S21D—C22D—H23D	109.5
H21A—C22A—H23A	109.5	H21D—C22D—H23D	109.5
H22A—C22A—H23A	109.5	H22D—C22D—H23D	109.5
C4A—N3A—C2A	114.93 (16)	C4D—N3D—C2D	115.09 (16)
N3A—C4A—C5A	124.79 (17)	N3D—C4D—C5D	124.76 (17)
N3A—C4A—Cl4A	116.54 (14)	N3D—C4D—Cl4D	116.48 (14)
C5A—C4A—Cl4A	118.67 (15)	C5D—C4D—Cl4D	118.76 (15)
C6A—C5A—C4A	113.77 (17)	C6D—C5D—C4D	113.92 (18)
C6A—C5A—H5A	123.1	C6D—C5D—H5D	123.0
C4A—C5A—H5A	123.1	C4D—C5D—H5D	123.0
N1A—C6A—C5A	125.29 (17)	N1D—C6D—C5D	124.98 (17)
N1A—C6A—Cl6A	115.95 (14)	N1D—C6D—Cl6D	116.32 (14)
C5A—C6A—Cl6A	118.75 (15)	C5D—C6D—Cl6D	118.70 (15)
C6B—N1B—C2B	114.52 (16)	C6E—N1E—C2E	114.50 (16)
N1B—C2B—N3B	126.82 (17)	N1E—C2E—N3E	126.64 (17)
N1B—C2B—S21B	119.81 (15)	N1E—C2E—S21E	119.97 (15)
N3B—C2B—S21B	113.35 (13)	N3E—C2E—S21E	113.38 (13)
C2B—S21B—C22B	102.40 (9)	C2E—S21E—C22E	102.32 (9)
S21B—C22B—H21B	109.5	S21E—C22E—H21E	109.5
S21B—C22B—H22B	109.5	S21E—C22E—H22E	109.5
H21B—C22B—H22B	109.5	H21E—C22E—H22E	109.5
S21B—C22B—H23B	109.5	S21E—C22E—H23E	109.5
H21B—C22B—H23B	109.5	H21E—C22E—H23E	109.5
H22B—C22B—H23B	109.5	H22E—C22E—H23E	109.5
C4B—N3B—C2B	114.70 (16)	C4E—N3E—C2E	114.97 (16)
N3B—C4B—C5B	125.12 (18)	N3E—C4E—C5E	124.80 (18)
N3B—C4B—Cl4B	116.42 (14)	N3E—C4E—Cl4E	116.45 (14)
C5B—C4B—Cl4B	118.46 (15)	C5E—C4E—Cl4E	118.75 (15)
C6B—C5B—C4B	113.88 (17)	C6E—C5E—C4E	113.80 (17)
C6B—C5B—H5B	123.1	C6E—C5E—H5E	123.1
C4B—C5B—H5B	123.1	C4E—C5E—H5E	123.1
N1B—C6B—C5B	124.92 (17)	N1E—C6E—C5E	125.27 (17)
N1B—C6B—Cl6B	116.14 (14)	N1E—C6E—Cl6E	116.18 (14)
C5B—C6B—Cl6B	118.94 (14)	C5E—C6E—Cl6E	118.56 (14)
C6C—N1C—C2C	114.44 (16)	C6F—N1F—C2F	114.86 (16)
N3C—C2C—N1C	126.68 (17)	N1F—C2F—N3F	126.53 (17)
N3C—C2C—S21C	113.48 (14)	N1F—C2F—S21F	120.05 (14)
N1C—C2C—S21C	119.83 (14)	N3F—C2F—S21F	113.40 (14)
C2C—S21C—C22C	102.01 (10)	C2F—S21F—C22F	102.17 (10)
S21C—C22C—H21C	109.5	S21F—C22F—H21F	109.5
S21C—C22C—H22C	109.5	S21F—C22F—H22F	109.5
H21C—C22C—H22C	109.5	H21F—C22F—H22F	109.5
S21C—C22C—H23C	109.5	S21F—C22F—H23F	109.5
H21C—C22C—H23C	109.5	H21F—C22F—H23F	109.5
H22C—C22C—H23C	109.5	H22F—C22F—H23F	109.5
C4C—N3C—C2C	114.80 (16)	C4F—N3F—C2F	114.87 (16)
N3C—C4C—C5C	124.86 (17)	N3F—C4F—C5F	124.90 (17)
N3C—C4C—Cl4C	116.32 (14)	N3F—C4F—Cl4F	116.34 (15)
C5C—C4C—Cl4C	118.82 (14)	C5F—C4F—Cl4F	118.76 (14)
C6C—C5C—C4C	113.92 (17)	C6F—C5F—C4F	114.14 (16)
C6C—C5C—H5C	123.0	C6F—C5F—H5F	122.9
C4C—C5C—H5C	123.0	C4F—C5F—H5F	122.9
N1C—C6C—C5C	125.24 (18)	N1F—C6F—C5F	124.67 (17)
N1C—C6C—Cl6C	115.95 (14)	N1F—C6F—Cl6F	116.37 (14)
C5C—C6C—Cl6C	118.80 (14)	C5F—C6F—Cl6F	118.95 (14)
C6A—N1A—C2A—N3A	0.6 (2)	C6D—N1D—C2D—N3D	1.7 (2)
C6A—N1A—C2A—S21A	−179.88 (12)	C6D—N1D—C2D—S21D	−176.41 (12)
N1A—C2A—S21A—C22A	−2.21 (16)	N1D—C2D—S21D—C22D	−1.92 (16)
N3A—C2A—S21A—C22A	177.34 (13)	N3D—C2D—S21D—C22D	179.71 (13)
N1A—C2A—N3A—C4A	0.7 (3)	N1D—C2D—N3D—C4D	−0.8 (3)
S21A—C2A—N3A—C4A	−178.78 (13)	S21D—C2D—N3D—C4D	177.47 (12)
C2A—N3A—C4A—C5A	−2.0 (3)	C2D—N3D—C4D—C5D	−0.6 (3)
C2A—N3A—C4A—Cl4A	178.22 (12)	C2D—N3D—C4D—Cl4D	−179.73 (12)
N3A—C4A—C5A—C6A	1.8 (3)	N3D—C4D—C5D—C6D	0.8 (3)
Cl4A—C4A—C5A—C6A	−178.45 (13)	Cl4D—C4D—C5D—C6D	179.94 (13)
C2A—N1A—C6A—C5A	−0.9 (3)	C2D—N1D—C6D—C5D	−1.4 (3)
C2A—N1A—C6A—Cl6A	−179.95 (12)	C2D—N1D—C6D—Cl6D	177.94 (12)
C4A—C5A—C6A—N1A	−0.2 (3)	C4D—C5D—C6D—N1D	0.3 (3)
C4A—C5A—C6A—Cl6A	178.83 (13)	C4D—C5D—C6D—Cl6D	−179.09 (12)
C6B—N1B—C2B—N3B	2.0 (3)	C6E—N1E—C2E—N3E	−0.3 (3)
C6B—N1B—C2B—S21B	−176.84 (12)	C6E—N1E—C2E—S21E	179.64 (12)
N1B—C2B—S21B—C22B	0.11 (16)	N1E—C2E—S21E—C22E	2.69 (16)
N3B—C2B—S21B—C22B	−178.90 (13)	N3E—C2E—S21E—C22E	−177.34 (13)
N1B—C2B—N3B—C4B	−2.2 (3)	N1E—C2E—N3E—C4E	−0.9 (3)
S21B—C2B—N3B—C4B	176.71 (12)	S21E—C2E—N3E—C4E	179.18 (12)
C2B—N3B—C4B—C5B	0.7 (3)	C2E—N3E—C4E—C5E	1.5 (3)
C2B—N3B—C4B—Cl4B	−179.05 (12)	C2E—N3E—C4E—Cl4E	−178.59 (12)
N3B—C4B—C5B—C6B	0.8 (3)	N3E—C4E—C5E—C6E	−1.0 (3)
Cl4B—C4B—C5B—C6B	−179.50 (13)	Cl4E—C4E—C5E—C6E	179.14 (13)
C2B—N1B—C6B—C5B	−0.3 (2)	C2E—N1E—C6E—C5E	1.0 (2)
C2B—N1B—C6B—Cl6B	179.90 (12)	C2E—N1E—C6E—Cl6E	−179.40 (12)
C4B—C5B—C6B—N1B	−1.0 (3)	C4E—C5E—C6E—N1E	−0.4 (3)
C4B—C5B—C6B—Cl6B	178.83 (13)	C4E—C5E—C6E—Cl6E	180.00 (13)
C6C—N1C—C2C—N3C	−2.6 (3)	C6F—N1F—C2F—N3F	−1.4 (3)
C6C—N1C—C2C—S21C	176.88 (12)	C6F—N1F—C2F—S21F	177.31 (12)
N3C—C2C—S21C—C22C	−177.40 (13)	N1F—C2F—S21F—C22F	−0.30 (17)
N1C—C2C—S21C—C22C	3.07 (16)	N3F—C2F—S21F—C22F	178.56 (13)
N1C—C2C—N3C—C4C	1.7 (2)	N1F—C2F—N3F—C4F	1.7 (3)
S21C—C2C—N3C—C4C	−177.83 (12)	S21F—C2F—N3F—C4F	−177.09 (13)
C2C—N3C—C4C—C5C	0.7 (3)	C2F—N3F—C4F—C5F	−1.2 (3)
C2C—N3C—C4C—Cl4C	−179.53 (12)	C2F—N3F—C4F—Cl4F	178.19 (12)
N3C—C4C—C5C—C6C	−1.8 (3)	N3F—C4F—C5F—C6F	0.6 (3)
Cl4C—C4C—C5C—C6C	178.46 (13)	Cl4F—C4F—C5F—C6F	−178.82 (13)
C2C—N1C—C6C—C5C	1.3 (3)	C2F—N1F—C6F—C5F	0.6 (3)
C2C—N1C—C6C—Cl6C	−179.66 (12)	C2F—N1F—C6F—Cl6F	−178.35 (12)
C4C—C5C—C6C—N1C	0.7 (3)	C4F—C5F—C6F—N1F	−0.2 (3)
C4C—C5C—C6C—Cl6C	−178.35 (13)	C4F—C5F—C6F—Cl6F	178.69 (13)