Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807015139/hb2351sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807015139/hb2351Isup2.hkl |
CCDC reference: 614707
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C21H12Cl4N2O2S3 | Z = 4 |
Mr = 562.31 | F(000) = 1136 |
Triclinic, P1 | Dx = 1.636 Mg m−3 |
Hall symbol: -P 1 | Cu Kα radiation, λ = 1.54184 Å |
a = 8.0420 (7) Å | Cell parameters from 15 reflections |
b = 14.359 (2) Å | θ = 12.8–23.6° |
c = 21.2641 (15) Å | µ = 7.49 mm−1 |
α = 100.386 (8)° | T = 293 K |
β = 99.594 (7)° | Prism, yellow |
γ = 104.237 (10)° | 0.27 × 0.24 × 0.18 mm |
V = 2283.0 (4) Å3 |
Enraf–Nonius CAD-4 diffractometer | 3186 reflections with I > 2σ(I) |
Radiation source: Enraf–Nonius FR590 | Rint = 0.111 |
Graphite monochromator | θmax = 70.8°, θmin = 2.2° |
Nonprofiled ω scans | h = −9→9 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→17 |
Tmin = 0.237, Tmax = 0.346 | l = −26→25 |
9143 measured reflections | 3 standard reflections every 120 min |
8769 independent reflections | intensity decay: −14% |
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)] = 0.076 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.221 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0668P)2 + 1.0407P] where P = (Fo2 + 2Fc2)/3 |
8769 reflections | (Δ/σ)max = 0.012 |
577 parameters | Δρmax = 0.42 e Å−3 |
0 restraints | Δρmin = −0.47 e Å−3 |
Experimental. Spectroscopic analysis: νIR (cm-1)(CO):1739, 1679; 1H-NMR (CDCl3, 400 MHz, δ, p.p.m.): 4.48 (s, 2H, S—CH2), 4.99 (s, 2H, N—CH2), 7.16 (d, 1H, 2''-H), 7.22 (dd, 1H, 3''-H), 7.31 (d, 2H,2',6'-H),7.35 (d, 2H, 3',5'-H), 7.41(d, 1H, 5''-H), 8.03 (s, 1H, H—C═C). |
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. |
x | y | z | Uiso*/Ueq | ||
S2 | 0.0495 (3) | 0.15695 (17) | 0.40492 (11) | 0.0518 (6) | |
S1' | −0.2860 (3) | 0.53137 (18) | 0.56354 (11) | 0.0545 (7) | |
S3' | −0.1692 (3) | 0.33630 (18) | 0.29760 (11) | 0.0568 (7) | |
Cl3' | −0.5312 (3) | 0.10816 (17) | 0.42955 (11) | 0.0552 (6) | |
S2' | −0.2544 (3) | 0.39635 (17) | 0.42791 (11) | 0.0488 (6) | |
S1 | 0.0481 (3) | 0.29483 (18) | 0.54350 (11) | 0.0563 (7) | |
Cl2' | −0.5598 (3) | 0.54508 (18) | 0.86087 (11) | 0.0604 (7) | |
Cl2 | −0.1912 (3) | 0.3199 (2) | 0.84627 (12) | 0.0677 (8) | |
S3 | 0.1275 (3) | 0.08479 (18) | 0.27410 (12) | 0.0592 (7) | |
Cl3 | −0.3067 (3) | −0.11438 (18) | 0.39718 (12) | 0.0666 (8) | |
Cl1 | 0.4679 (4) | 0.3150 (2) | 0.93491 (13) | 0.0933 (10) | |
Cl1' | 0.1191 (4) | 0.6053 (3) | 0.96624 (13) | 0.1019 (12) | |
Cl4' | −0.8824 (4) | 0.1699 (2) | 0.02897 (14) | 0.1004 (11) | |
Cl4 | 0.7011 (4) | −0.0388 (2) | 0.10048 (14) | 0.0947 (10) | |
N1' | −0.4106 (9) | 0.5087 (5) | 0.6667 (3) | 0.0448 (18) | |
N2' | −0.3566 (9) | 0.2153 (5) | 0.3613 (3) | 0.0492 (19) | |
O2' | −0.5094 (8) | 0.3398 (5) | 0.6500 (3) | 0.0631 (19) | |
O1' | −0.2981 (8) | 0.6699 (5) | 0.6631 (3) | 0.0633 (19) | |
N1 | −0.0775 (10) | 0.2763 (6) | 0.6473 (3) | 0.053 (2) | |
O2 | −0.2361 (8) | 0.1138 (5) | 0.6218 (3) | 0.068 (2) | |
N2 | −0.0955 (9) | −0.0171 (6) | 0.3338 (3) | 0.054 (2) | |
C13' | −0.4131 (10) | 0.2190 (6) | 0.4173 (4) | 0.039 (2) | |
O1 | 0.0880 (9) | 0.4321 (5) | 0.6510 (3) | 0.082 (2) | |
C6 | 0.0293 (10) | 0.2951 (6) | 0.7652 (4) | 0.044 (2) | |
C12' | −0.3739 (10) | 0.3073 (7) | 0.4613 (4) | 0.047 (2) | |
C12 | −0.0970 (10) | 0.0741 (6) | 0.4348 (4) | 0.038 (2) | |
C11 | −0.1354 (11) | 0.0957 (7) | 0.4983 (4) | 0.054 (3) | |
H11 | −0.2060 | 0.0420 | 0.5092 | 0.065* | |
C9 | −0.0879 (11) | 0.1788 (6) | 0.5441 (4) | 0.046 (2) | |
C1 | 0.0059 (11) | 0.3096 (6) | 0.8290 (4) | 0.045 (2) | |
C14' | −0.2692 (10) | 0.3043 (6) | 0.3596 (4) | 0.045 (2) | |
C7' | −0.4621 (11) | 0.5279 (7) | 0.7298 (3) | 0.048 (2) | |
H7'1 | −0.5579 | 0.4721 | 0.7307 | 0.057* | |
H7'2 | −0.5052 | 0.5856 | 0.7334 | 0.057* | |
C16 | 0.2488 (12) | −0.0475 (6) | 0.1989 (4) | 0.049 (2) | |
C1' | −0.3501 (11) | 0.5521 (6) | 0.8489 (4) | 0.046 (2) | |
C6' | −0.3134 (11) | 0.5447 (6) | 0.7881 (4) | 0.042 (2) | |
C13 | −0.1593 (11) | −0.0128 (7) | 0.3890 (4) | 0.050 (2) | |
C8' | −0.4460 (11) | 0.4100 (7) | 0.6321 (4) | 0.044 (2) | |
C4' | −0.0063 (12) | 0.5732 (7) | 0.8367 (4) | 0.061 (3) | |
H4' | 0.1093 | 0.5811 | 0.8324 | 0.074* | |
C2' | −0.2185 (14) | 0.5710 (7) | 0.9041 (5) | 0.067 (3) | |
H2' | −0.2443 | 0.5764 | 0.9454 | 0.081* | |
C10' | −0.3277 (12) | 0.5843 (8) | 0.6398 (4) | 0.057 (3) | |
C11' | −0.4206 (10) | 0.3252 (6) | 0.5240 (4) | 0.044 (2) | |
H11' | −0.4868 | 0.2698 | 0.5347 | 0.053* | |
C21' | −0.5565 (12) | 0.2094 (6) | 0.2011 (4) | 0.053 (3) | |
H21' | −0.5659 | 0.2142 | 0.2445 | 0.063* | |
C19 | 0.5250 (14) | −0.0467 (7) | 0.1383 (5) | 0.063 (3) | |
C8 | −0.1392 (12) | 0.1823 (8) | 0.6072 (5) | 0.058 (3) | |
C5' | −0.1446 (11) | 0.5521 (6) | 0.7825 (4) | 0.053 (3) | |
H5' | −0.1209 | 0.5427 | 0.7409 | 0.063* | |
C9' | −0.3823 (10) | 0.4099 (6) | 0.5689 (4) | 0.038 (2) | |
C15' | −0.2391 (11) | 0.2201 (6) | 0.2374 (4) | 0.056 (3) | |
H15A | −0.1425 | 0.2131 | 0.2168 | 0.067* | |
H15B | −0.2664 | 0.1667 | 0.2596 | 0.067* | |
C2 | 0.1381 (13) | 0.3106 (6) | 0.8806 (5) | 0.058 (3) | |
H2 | 0.1192 | 0.3173 | 0.9230 | 0.070* | |
C20 | 0.5451 (13) | −0.0427 (7) | 0.2038 (4) | 0.061 (3) | |
H20 | 0.6545 | −0.0401 | 0.2279 | 0.074* | |
C16' | −0.3974 (13) | 0.2108 (6) | 0.1851 (4) | 0.055 (3) | |
C21 | 0.4124 (13) | −0.0424 (7) | 0.2346 (5) | 0.058 (3) | |
H21 | 0.4303 | −0.0389 | 0.2794 | 0.070* | |
C14 | 0.0149 (12) | 0.0666 (7) | 0.3338 (4) | 0.055 (3) | |
C20' | −0.7030 (13) | 0.2008 (6) | 0.1533 (5) | 0.062 (3) | |
H20' | −0.8073 | 0.2049 | 0.1655 | 0.074* | |
C18 | 0.3612 (14) | −0.0508 (7) | 0.1025 (5) | 0.065 (3) | |
H18 | 0.3456 | −0.0524 | 0.0579 | 0.078* | |
C7 | −0.1141 (11) | 0.3000 (7) | 0.7112 (4) | 0.056 (3) | |
H7A | −0.2243 | 0.2544 | 0.7123 | 0.067* | |
H7B | −0.1280 | 0.3661 | 0.7192 | 0.067* | |
C10 | 0.0196 (14) | 0.3460 (9) | 0.6234 (5) | 0.067 (3) | |
C3' | −0.0499 (12) | 0.5817 (7) | 0.8971 (4) | 0.056 (3) | |
C17' | −0.3881 (13) | 0.1995 (7) | 0.1204 (4) | 0.061 (3) | |
H17' | −0.2820 | 0.1995 | 0.1085 | 0.074* | |
C3 | 0.2952 (12) | 0.3017 (7) | 0.8688 (4) | 0.056 (3) | |
C5 | 0.1889 (12) | 0.2823 (6) | 0.7551 (4) | 0.052 (2) | |
H5 | 0.2065 | 0.2702 | 0.7126 | 0.062* | |
C19' | −0.6962 (15) | 0.1860 (8) | 0.0867 (5) | 0.071 (3) | |
C15 | 0.0985 (12) | −0.0412 (6) | 0.2326 (5) | 0.067 (3) | |
H15C | 0.0944 | −0.0825 | 0.2640 | 0.080* | |
H15D | −0.0121 | −0.0654 | 0.2003 | 0.080* | |
C4 | 0.3224 (13) | 0.2871 (7) | 0.8068 (4) | 0.064 (3) | |
H4 | 0.4300 | 0.2804 | 0.7992 | 0.077* | |
C17 | 0.2238 (13) | −0.0527 (7) | 0.1321 (4) | 0.065 (3) | |
H17 | 0.1135 | −0.0574 | 0.1077 | 0.077* | |
C18' | −0.5361 (15) | 0.1881 (7) | 0.0730 (5) | 0.067 (3) | |
H18' | −0.5260 | 0.1815 | 0.0296 | 0.081* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S2 | 0.0522 (15) | 0.0487 (15) | 0.0524 (15) | 0.0088 (12) | 0.0175 (12) | 0.0089 (12) |
S1' | 0.0673 (17) | 0.0528 (16) | 0.0406 (14) | 0.0097 (13) | 0.0135 (12) | 0.0126 (12) |
S3' | 0.0587 (16) | 0.0590 (17) | 0.0449 (14) | 0.0018 (13) | 0.0172 (12) | 0.0076 (13) |
Cl3' | 0.0543 (14) | 0.0528 (15) | 0.0536 (15) | 0.0085 (12) | 0.0084 (11) | 0.0129 (12) |
S2' | 0.0537 (15) | 0.0485 (15) | 0.0389 (13) | 0.0060 (12) | 0.0081 (11) | 0.0110 (12) |
S1 | 0.0637 (17) | 0.0532 (16) | 0.0464 (15) | 0.0075 (13) | 0.0073 (12) | 0.0148 (12) |
Cl2' | 0.0619 (16) | 0.0712 (18) | 0.0559 (15) | 0.0245 (14) | 0.0302 (12) | 0.0111 (13) |
Cl2 | 0.0618 (16) | 0.083 (2) | 0.0602 (16) | 0.0240 (15) | 0.0231 (13) | 0.0073 (14) |
S3 | 0.0768 (19) | 0.0528 (17) | 0.0517 (15) | 0.0154 (14) | 0.0296 (14) | 0.0115 (13) |
Cl3 | 0.0662 (17) | 0.0551 (16) | 0.0680 (17) | −0.0040 (13) | 0.0222 (14) | 0.0109 (14) |
Cl1 | 0.073 (2) | 0.132 (3) | 0.0682 (19) | 0.0209 (19) | −0.0100 (15) | 0.0419 (19) |
Cl1' | 0.069 (2) | 0.160 (3) | 0.0603 (19) | 0.011 (2) | −0.0088 (15) | 0.036 (2) |
Cl4' | 0.106 (3) | 0.110 (3) | 0.0633 (19) | 0.025 (2) | −0.0186 (17) | 0.0086 (18) |
Cl4 | 0.083 (2) | 0.114 (3) | 0.086 (2) | 0.0312 (19) | 0.0386 (18) | −0.0025 (19) |
N1' | 0.048 (5) | 0.050 (5) | 0.036 (4) | 0.017 (4) | 0.001 (3) | 0.015 (4) |
N2' | 0.046 (5) | 0.047 (5) | 0.048 (5) | 0.000 (4) | 0.022 (4) | 0.002 (4) |
O2' | 0.082 (5) | 0.053 (4) | 0.043 (4) | 0.001 (4) | 0.014 (3) | 0.009 (3) |
O1' | 0.078 (5) | 0.044 (4) | 0.068 (5) | 0.019 (4) | 0.011 (4) | 0.014 (4) |
N1 | 0.067 (5) | 0.066 (6) | 0.022 (4) | 0.023 (5) | 0.005 (4) | −0.001 (4) |
O2 | 0.065 (5) | 0.068 (5) | 0.058 (4) | −0.001 (4) | 0.017 (4) | 0.007 (4) |
N2 | 0.052 (5) | 0.066 (6) | 0.043 (4) | 0.008 (4) | 0.006 (4) | 0.023 (4) |
C13' | 0.031 (5) | 0.050 (6) | 0.040 (5) | 0.016 (4) | 0.008 (4) | 0.010 (4) |
O1 | 0.103 (6) | 0.037 (4) | 0.081 (5) | −0.012 (4) | 0.008 (4) | 0.011 (4) |
C6 | 0.029 (5) | 0.063 (6) | 0.039 (5) | 0.020 (5) | −0.004 (4) | 0.008 (5) |
C12' | 0.028 (5) | 0.069 (7) | 0.052 (6) | 0.013 (5) | 0.013 (4) | 0.033 (5) |
C12 | 0.034 (5) | 0.038 (5) | 0.041 (5) | 0.009 (4) | 0.001 (4) | 0.012 (4) |
C11 | 0.062 (6) | 0.055 (7) | 0.036 (5) | 0.013 (5) | −0.001 (5) | 0.003 (5) |
C9 | 0.060 (6) | 0.042 (6) | 0.037 (5) | 0.018 (5) | 0.004 (4) | 0.012 (4) |
C1 | 0.040 (5) | 0.049 (6) | 0.040 (5) | 0.008 (4) | 0.003 (4) | 0.009 (4) |
C14' | 0.037 (5) | 0.046 (6) | 0.043 (5) | −0.002 (4) | 0.003 (4) | 0.014 (5) |
C7' | 0.060 (6) | 0.067 (7) | 0.028 (5) | 0.034 (5) | 0.014 (4) | 0.016 (5) |
C16 | 0.056 (6) | 0.047 (6) | 0.050 (6) | 0.018 (5) | 0.014 (5) | 0.016 (5) |
C1' | 0.051 (6) | 0.033 (5) | 0.057 (6) | 0.012 (4) | 0.020 (5) | 0.011 (5) |
C6' | 0.040 (5) | 0.050 (6) | 0.040 (5) | 0.019 (4) | 0.007 (4) | 0.015 (4) |
C13 | 0.048 (6) | 0.052 (6) | 0.045 (5) | −0.003 (5) | 0.011 (4) | 0.025 (5) |
C8' | 0.032 (5) | 0.060 (7) | 0.040 (5) | 0.017 (5) | 0.007 (4) | 0.010 (5) |
C4' | 0.048 (6) | 0.097 (9) | 0.044 (6) | 0.025 (6) | 0.004 (5) | 0.030 (6) |
C2' | 0.080 (8) | 0.069 (7) | 0.048 (6) | 0.011 (6) | 0.020 (6) | 0.010 (5) |
C10' | 0.057 (6) | 0.075 (8) | 0.039 (6) | 0.021 (6) | 0.004 (5) | 0.016 (6) |
C11' | 0.035 (5) | 0.048 (6) | 0.043 (5) | −0.002 (4) | 0.003 (4) | 0.016 (5) |
C21' | 0.070 (7) | 0.051 (6) | 0.028 (5) | 0.003 (5) | 0.006 (5) | 0.009 (4) |
C19 | 0.089 (8) | 0.072 (7) | 0.047 (6) | 0.053 (6) | 0.024 (6) | 0.012 (5) |
C8 | 0.053 (6) | 0.060 (7) | 0.042 (6) | 0.000 (5) | −0.008 (5) | 0.002 (5) |
C5' | 0.053 (6) | 0.073 (7) | 0.039 (5) | 0.021 (5) | 0.020 (5) | 0.014 (5) |
C9' | 0.028 (4) | 0.041 (5) | 0.036 (5) | −0.001 (4) | −0.003 (4) | 0.006 (4) |
C15' | 0.072 (7) | 0.057 (6) | 0.042 (5) | 0.035 (5) | 0.012 (5) | −0.004 (5) |
C2 | 0.069 (7) | 0.036 (5) | 0.058 (6) | −0.014 (5) | 0.018 (5) | 0.019 (5) |
C20 | 0.072 (7) | 0.072 (7) | 0.039 (6) | 0.021 (6) | 0.010 (5) | 0.010 (5) |
C16' | 0.076 (7) | 0.035 (5) | 0.050 (6) | 0.001 (5) | 0.026 (5) | 0.012 (5) |
C21 | 0.065 (7) | 0.071 (7) | 0.045 (6) | 0.034 (6) | 0.012 (5) | 0.009 (5) |
C14 | 0.065 (7) | 0.062 (7) | 0.047 (6) | 0.021 (6) | 0.020 (5) | 0.024 (5) |
C20' | 0.061 (7) | 0.051 (7) | 0.068 (7) | 0.004 (5) | 0.018 (6) | 0.014 (6) |
C18 | 0.095 (9) | 0.062 (7) | 0.058 (7) | 0.048 (6) | 0.020 (6) | 0.023 (5) |
C7 | 0.040 (6) | 0.058 (7) | 0.066 (7) | 0.020 (5) | 0.004 (5) | 0.005 (5) |
C10 | 0.071 (7) | 0.072 (8) | 0.040 (6) | 0.006 (6) | −0.014 (5) | 0.019 (6) |
C3' | 0.045 (6) | 0.072 (7) | 0.046 (6) | 0.019 (5) | −0.012 (5) | 0.017 (5) |
C17' | 0.078 (8) | 0.064 (7) | 0.038 (6) | 0.015 (6) | 0.007 (5) | 0.014 (5) |
C3 | 0.049 (6) | 0.071 (7) | 0.048 (6) | 0.012 (5) | 0.000 (5) | 0.028 (5) |
C5 | 0.066 (7) | 0.040 (6) | 0.045 (6) | 0.018 (5) | 0.010 (5) | 0.001 (4) |
C19' | 0.091 (9) | 0.072 (8) | 0.046 (6) | 0.033 (7) | −0.003 (6) | 0.006 (6) |
C15 | 0.074 (7) | 0.046 (6) | 0.069 (7) | 0.008 (5) | 0.019 (6) | −0.006 (5) |
C4 | 0.059 (7) | 0.085 (8) | 0.039 (6) | 0.004 (6) | 0.004 (5) | 0.018 (6) |
C17 | 0.062 (7) | 0.084 (8) | 0.046 (6) | 0.033 (6) | 0.007 (5) | 0.000 (6) |
C18' | 0.104 (9) | 0.058 (7) | 0.042 (6) | 0.027 (7) | 0.018 (6) | 0.007 (5) |
S2—C12 | 1.742 (8) | C7'—H7'2 | 0.9700 |
S2—C14 | 1.738 (9) | C16—C21 | 1.383 (11) |
S1'—C9' | 1.757 (8) | C16—C17 | 1.388 (11) |
S1'—C10' | 1.785 (10) | C16—C15 | 1.516 (11) |
S3'—C14' | 1.728 (8) | C1'—C6' | 1.365 (10) |
S3'—C15' | 1.806 (8) | C1'—C2' | 1.379 (11) |
Cl3'—C13' | 1.729 (9) | C6'—C5' | 1.363 (10) |
S2'—C12' | 1.736 (8) | C8'—C9' | 1.514 (11) |
S2'—C14' | 1.744 (9) | C4'—C5' | 1.392 (10) |
S1—C9 | 1.756 (9) | C4'—C3' | 1.379 (11) |
S1—C10 | 1.800 (10) | C4'—H4' | 0.9300 |
Cl2'—C1' | 1.729 (8) | C2'—C3' | 1.363 (11) |
Cl2—C1 | 1.721 (8) | C2'—H2' | 0.9300 |
S3—C14 | 1.700 (9) | C11'—C9' | 1.338 (10) |
S3—C15 | 1.804 (8) | C11'—H11' | 0.9300 |
Cl3—C13 | 1.695 (8) | C21'—C16' | 1.375 (11) |
Cl1—C3 | 1.749 (9) | C21'—C20' | 1.386 (11) |
Cl1'—C3' | 1.746 (8) | C21'—H21' | 0.9300 |
Cl4'—C19' | 1.707 (10) | C19—C18 | 1.389 (12) |
Cl4—C19 | 1.732 (10) | C19—C20 | 1.363 (11) |
N1'—C10' | 1.394 (11) | C5'—H5' | 0.9300 |
N1'—C8' | 1.408 (10) | C15'—C16' | 1.506 (12) |
N1'—C7' | 1.468 (9) | C15'—H15A | 0.9700 |
N2'—C14' | 1.308 (9) | C15'—H15B | 0.9700 |
N2'—C13' | 1.340 (9) | C2—C3 | 1.360 (11) |
O2'—C8' | 1.173 (10) | C2—H2 | 0.9300 |
O1'—C10' | 1.187 (10) | C20—C21 | 1.343 (11) |
N1—C10 | 1.342 (11) | C20—H20 | 0.9300 |
N1—C8 | 1.381 (11) | C16'—C17' | 1.373 (11) |
N1—C7 | 1.437 (10) | C21—H21 | 0.9300 |
O2—C8 | 1.218 (10) | C20'—C19' | 1.407 (12) |
N2—C14 | 1.305 (10) | C20'—H20' | 0.9300 |
N2—C13 | 1.355 (10) | C18—C17 | 1.357 (11) |
C13'—C12' | 1.363 (11) | C18—H18 | 0.9300 |
O1—C10 | 1.213 (11) | C7—H7A | 0.9700 |
C6—C5 | 1.385 (10) | C7—H7B | 0.9700 |
C6—C1 | 1.387 (11) | C17'—C18' | 1.379 (12) |
C6—C7 | 1.510 (10) | C17'—H17' | 0.9300 |
C12'—C11' | 1.439 (11) | C3—C4 | 1.362 (11) |
C12—C13 | 1.359 (10) | C5—C4 | 1.381 (11) |
C12—C11 | 1.432 (10) | C5—H5 | 0.9300 |
C11—C9 | 1.324 (10) | C19'—C18' | 1.361 (13) |
C11—H11 | 0.9300 | C15—H15C | 0.9700 |
C9—C8 | 1.464 (12) | C15—H15D | 0.9700 |
C1—C2 | 1.391 (11) | C4—H4 | 0.9300 |
C7'—C6' | 1.511 (10) | C17—H17 | 0.9300 |
C7'—H7'1 | 0.9700 | C18'—H18' | 0.9300 |
C12—S2—C14 | 89.8 (4) | C20—C19—Cl4 | 121.6 (8) |
C9'—S1'—C10' | 93.1 (5) | O2—C8—N1 | 122.7 (9) |
C14'—S3'—C15' | 101.5 (4) | O2—C8—C9 | 125.2 (9) |
C12'—S2'—C14' | 89.3 (4) | N1—C8—C9 | 111.8 (9) |
C9—S1—C10 | 90.5 (5) | C6'—C5'—C4' | 122.5 (8) |
C14—S3—C15 | 100.7 (5) | C6'—C5'—H5' | 118.7 |
C10'—N1'—C8' | 118.8 (8) | C4'—C5'—H5' | 118.7 |
C10'—N1'—C7' | 122.5 (8) | C11'—C9'—C8' | 119.6 (8) |
C8'—N1'—C7' | 118.7 (7) | C11'—C9'—S1' | 129.4 (7) |
C14'—N2'—C13' | 109.2 (7) | C8'—C9'—S1' | 110.5 (6) |
C10—N1—C8 | 116.3 (8) | C16'—C15'—S3' | 113.4 (6) |
C10—N1—C7 | 120.9 (8) | C16'—C15'—H15A | 108.9 |
C8—N1—C7 | 122.8 (9) | S3'—C15'—H15A | 108.9 |
C14—N2—C13 | 112.2 (8) | C16'—C15'—H15B | 108.9 |
N2'—C13'—C12' | 119.6 (8) | S3'—C15'—H15B | 108.9 |
N2'—C13'—Cl3' | 116.6 (7) | H15A—C15'—H15B | 107.7 |
C12'—C13'—Cl3' | 123.8 (7) | C3—C2—C1 | 119.6 (9) |
C5—C6—C1 | 117.5 (8) | C3—C2—H2 | 120.2 |
C5—C6—C7 | 123.5 (8) | C1—C2—H2 | 120.2 |
C1—C6—C7 | 118.9 (8) | C21—C20—C19 | 122.3 (10) |
C13'—C12'—C11' | 127.4 (8) | C21—C20—H20 | 118.9 |
C13'—C12'—S2' | 107.0 (6) | C19—C20—H20 | 118.9 |
C11'—C12'—S2' | 125.6 (7) | C21'—C16'—C17' | 118.7 (10) |
C13—C12—C11 | 127.5 (8) | C21'—C16'—C15' | 120.2 (8) |
C13—C12—S2 | 108.2 (6) | C17'—C16'—C15' | 121.1 (9) |
C11—C12—S2 | 124.2 (7) | C20—C21—C16 | 119.2 (9) |
C9—C11—C12 | 131.3 (9) | C20—C21—H21 | 120.4 |
C9—C11—H11 | 114.4 | C16—C21—H21 | 120.4 |
C12—C11—H11 | 114.4 | N2—C14—S3 | 124.4 (7) |
C11—C9—C8 | 121.4 (9) | N2—C14—S2 | 113.1 (7) |
C11—C9—S1 | 128.5 (8) | S3—C14—S2 | 122.4 (6) |
C8—C9—S1 | 110.0 (7) | C19'—C20'—C21' | 121.0 (9) |
C2—C1—C6 | 120.9 (8) | C19'—C20'—H20' | 119.5 |
C2—C1—Cl2 | 117.9 (7) | C21'—C20'—H20' | 119.5 |
C6—C1—Cl2 | 121.2 (7) | C19—C18—C17 | 120.4 (10) |
N2'—C14'—S3' | 126.1 (7) | C19—C18—H18 | 119.8 |
N2'—C14'—S2' | 114.8 (6) | C17—C18—H18 | 119.8 |
S3'—C14'—S2' | 119.0 (5) | N1—C7—C6 | 112.6 (7) |
N1'—C7'—C6' | 113.3 (7) | N1—C7—H7A | 109.1 |
N1'—C7'—H7'1 | 108.9 | C6—C7—H7A | 109.1 |
C6'—C7'—H7'1 | 108.9 | N1—C7—H7B | 109.1 |
N1'—C7'—H7'2 | 108.9 | C6—C7—H7B | 109.1 |
C6'—C7'—H7'2 | 108.9 | H7A—C7—H7B | 107.8 |
H7'1—C7'—H7'2 | 107.7 | O1—C10—N1 | 126.6 (10) |
C21—C16—C17 | 119.8 (9) | O1—C10—S1 | 122.1 (9) |
C21—C16—C15 | 120.8 (9) | N1—C10—S1 | 111.2 (8) |
C17—C16—C15 | 119.3 (9) | C2'—C3'—C4' | 122.4 (8) |
C6'—C1'—C2' | 121.0 (8) | C2'—C3'—Cl1' | 119.7 (8) |
C6'—C1'—Cl2' | 121.9 (7) | C4'—C3'—Cl1' | 117.9 (7) |
C2'—C1'—Cl2' | 117.0 (7) | C16'—C17'—C18' | 120.1 (10) |
C5'—C6'—C1' | 118.7 (8) | C16'—C17'—H17' | 120.0 |
C5'—C6'—C7' | 122.7 (7) | C18'—C17'—H17' | 120.0 |
C1'—C6'—C7' | 118.6 (8) | C2—C3—C4 | 121.0 (9) |
N2—C13—C12 | 116.6 (8) | C2—C3—Cl1 | 119.3 (8) |
N2—C13—Cl3 | 118.9 (7) | C4—C3—Cl1 | 119.6 (8) |
C12—C13—Cl3 | 124.5 (7) | C6—C5—C4 | 121.6 (9) |
O2'—C8'—N1' | 125.7 (8) | C6—C5—H5 | 119.2 |
O2'—C8'—C9' | 125.7 (9) | C4—C5—H5 | 119.2 |
N1'—C8'—C9' | 108.6 (8) | C18'—C19'—C20' | 116.2 (10) |
C5'—C4'—C3' | 116.4 (8) | C18'—C19'—Cl4' | 124.3 (9) |
C5'—C4'—H4' | 121.8 | C20'—C19'—Cl4' | 119.5 (9) |
C3'—C4'—H4' | 121.8 | C16—C15—S3 | 110.3 (6) |
C3'—C2'—C1' | 118.8 (9) | C16—C15—H15C | 109.6 |
C3'—C2'—H2' | 120.6 | S3—C15—H15C | 109.6 |
C1'—C2'—H2' | 120.6 | C16—C15—H15D | 109.6 |
O1'—C10'—N1' | 124.7 (9) | S3—C15—H15D | 109.6 |
O1'—C10'—S1' | 126.1 (8) | H15C—C15—H15D | 108.1 |
N1'—C10'—S1' | 109.0 (7) | C3—C4—C5 | 119.4 (9) |
C9'—C11'—C12' | 129.3 (8) | C3—C4—H4 | 120.3 |
C9'—C11'—H11' | 115.4 | C5—C4—H4 | 120.3 |
C12'—C11'—H11' | 115.4 | C18—C17—C16 | 119.6 (9) |
C16'—C21'—C20' | 120.7 (8) | C18—C17—H17 | 120.2 |
C16'—C21'—H21' | 119.7 | C16—C17—H17 | 120.2 |
C20'—C21'—H21' | 119.7 | C19'—C18'—C17' | 123.2 (10) |
C18—C19—C20 | 118.6 (9) | C19'—C18'—H18' | 118.4 |
C18—C19—Cl4 | 119.7 (8) | C17'—C18'—H18' | 118.4 |
C14'—N2'—C13'—C12' | −0.5 (11) | C3'—C4'—C5'—C6' | 3.0 (15) |
C14'—N2'—C13'—Cl3' | −179.6 (6) | C12'—C11'—C9'—C8' | −179.6 (8) |
N2'—C13'—C12'—C11' | −178.9 (8) | C12'—C11'—C9'—S1' | 8.9 (14) |
Cl3'—C13'—C12'—C11' | 0.1 (12) | O2'—C8'—C9'—C11' | 10.1 (14) |
N2'—C13'—C12'—S2' | 0.8 (9) | N1'—C8'—C9'—C11' | −171.9 (7) |
Cl3'—C13'—C12'—S2' | 179.9 (4) | O2'—C8'—C9'—S1' | −176.9 (8) |
C14'—S2'—C12'—C13' | −0.7 (6) | N1'—C8'—C9'—S1' | 1.1 (8) |
C14'—S2'—C12'—C11' | 179.1 (7) | C10'—S1'—C9'—C11' | 171.1 (8) |
C14—S2—C12—C13 | −0.5 (7) | C10'—S1'—C9'—C8' | −1.0 (6) |
C14—S2—C12—C11 | 177.0 (7) | C14'—S3'—C15'—C16' | 96.8 (7) |
C13—C12—C11—C9 | −176.2 (9) | C6—C1—C2—C3 | 2.9 (14) |
S2—C12—C11—C9 | 6.8 (14) | Cl2—C1—C2—C3 | 179.4 (7) |
C12—C11—C9—C8 | −177.8 (9) | C18—C19—C20—C21 | −0.1 (15) |
C12—C11—C9—S1 | −1.8 (15) | Cl4—C19—C20—C21 | 175.7 (8) |
C10—S1—C9—C11 | 179.6 (9) | C20'—C21'—C16'—C17' | −2.6 (14) |
C10—S1—C9—C8 | −4.0 (7) | C20'—C21'—C16'—C15' | 180.0 (8) |
C5—C6—C1—C2 | −0.3 (14) | S3'—C15'—C16'—C21' | −64.3 (10) |
C7—C6—C1—C2 | −176.8 (8) | S3'—C15'—C16'—C17' | 118.3 (9) |
C5—C6—C1—Cl2 | −176.7 (7) | C19—C20—C21—C16 | 0.7 (15) |
C7—C6—C1—Cl2 | 6.9 (12) | C17—C16—C21—C20 | 0.0 (14) |
C13'—N2'—C14'—S3' | 179.2 (6) | C15—C16—C21—C20 | −176.4 (9) |
C13'—N2'—C14'—S2' | −0.1 (9) | C13—N2—C14—S3 | 176.5 (7) |
C15'—S3'—C14'—N2' | 5.7 (9) | C13—N2—C14—S2 | 1.1 (10) |
C15'—S3'—C14'—S2' | −175.1 (5) | C15—S3—C14—N2 | −15.5 (9) |
C12'—S2'—C14'—N2' | 0.4 (7) | C15—S3—C14—S2 | 159.5 (6) |
C12'—S2'—C14'—S3' | −178.9 (5) | C12—S2—C14—N2 | −0.3 (7) |
C10'—N1'—C7'—C6' | −83.0 (10) | C12—S2—C14—S3 | −175.8 (6) |
C8'—N1'—C7'—C6' | 96.8 (9) | C16'—C21'—C20'—C19' | 4.7 (14) |
C2'—C1'—C6'—C5' | 2.9 (14) | C20—C19—C18—C17 | −1.2 (15) |
Cl2'—C1'—C6'—C5' | 179.2 (7) | Cl4—C19—C18—C17 | −177.1 (8) |
C2'—C1'—C6'—C7' | −177.6 (8) | C10—N1—C7—C6 | −86.1 (11) |
Cl2'—C1'—C6'—C7' | −1.3 (12) | C8—N1—C7—C6 | 94.2 (10) |
N1'—C7'—C6'—C5' | 6.9 (12) | C5—C6—C7—N1 | 8.2 (13) |
N1'—C7'—C6'—C1' | −172.6 (7) | C1—C6—C7—N1 | −175.6 (8) |
C14—N2—C13—C12 | −1.6 (12) | C8—N1—C10—O1 | −178.7 (10) |
C14—N2—C13—Cl3 | 179.3 (7) | C7—N1—C10—O1 | 1.6 (16) |
C11—C12—C13—N2 | −176.1 (8) | C8—N1—C10—S1 | −1.6 (11) |
S2—C12—C13—N2 | 1.3 (10) | C7—N1—C10—S1 | 178.7 (6) |
C11—C12—C13—Cl3 | 2.9 (14) | C9—S1—C10—O1 | −179.5 (9) |
S2—C12—C13—Cl3 | −179.7 (5) | C9—S1—C10—N1 | 3.3 (7) |
C10'—N1'—C8'—O2' | 177.3 (9) | C1'—C2'—C3'—C4' | −0.8 (15) |
C7'—N1'—C8'—O2' | −2.5 (13) | C1'—C2'—C3'—Cl1' | −179.7 (7) |
C10'—N1'—C8'—C9' | −0.6 (10) | C5'—C4'—C3'—C2' | −0.5 (15) |
C7'—N1'—C8'—C9' | 179.5 (6) | C5'—C4'—C3'—Cl1' | 178.5 (7) |
C6'—C1'—C2'—C3' | −0.4 (14) | C21'—C16'—C17'—C18' | 0.7 (14) |
Cl2'—C1'—C2'—C3' | −177.0 (7) | C15'—C16'—C17'—C18' | 178.1 (8) |
C8'—N1'—C10'—O1' | 176.6 (9) | C1—C2—C3—C4 | −3.1 (15) |
C7'—N1'—C10'—O1' | −3.5 (14) | C1—C2—C3—Cl1 | 173.8 (7) |
C8'—N1'—C10'—S1' | −0.1 (9) | C1—C6—C5—C4 | −2.2 (14) |
C7'—N1'—C10'—S1' | 179.7 (6) | C7—C6—C5—C4 | 174.1 (9) |
C9'—S1'—C10'—O1' | −176.0 (9) | C21'—C20'—C19'—C18' | −4.7 (15) |
C9'—S1'—C10'—N1' | 0.6 (7) | C21'—C20'—C19'—Cl4' | 176.9 (7) |
C13'—C12'—C11'—C9' | 178.7 (8) | C21—C16—C15—S3 | 76.3 (10) |
S2'—C12'—C11'—C9' | −1.0 (13) | C17—C16—C15—S3 | −100.1 (9) |
C10—N1—C8—O2 | −176.1 (9) | C14—S3—C15—C16 | −153.9 (7) |
C7—N1—C8—O2 | 3.7 (15) | C2—C3—C4—C5 | 0.7 (15) |
C10—N1—C8—C9 | −1.6 (12) | Cl1—C3—C4—C5 | −176.3 (7) |
C7—N1—C8—C9 | 178.2 (7) | C6—C5—C4—C3 | 2.0 (15) |
C11—C9—C8—O2 | −4.9 (16) | C19—C18—C17—C16 | 1.9 (15) |
S1—C9—C8—O2 | 178.4 (9) | C21—C16—C17—C18 | −1.3 (15) |
C11—C9—C8—N1 | −179.3 (8) | C15—C16—C17—C18 | 175.1 (9) |
S1—C9—C8—N1 | 4.0 (10) | C20'—C19'—C18'—C17' | 2.8 (16) |
C1'—C6'—C5'—C4' | −4.2 (14) | Cl4'—C19'—C18'—C17' | −178.8 (8) |
C7'—C6'—C5'—C4' | 176.3 (9) | C16'—C17'—C18'—C19' | −0.9 (16) |