Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806028595/fl2038sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806028595/fl2038Isup2.hkl |
CCDC reference: 621306
Data collection: CrysAlis CCD (Oxford Diffraction, 2000); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLEASE SUPPLY; software used to prepare material for publication: CIFTAB (Sheldrick, 1997).
C24H38N2O6S2 | F(000) = 1104 |
Mr = 514.68 | Dx = 1.335 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P2ac2ab | Cell parameters from 7818 reflections |
a = 8.4677 (3) Å | θ = 2.4–31.3° |
b = 11.1826 (4) Å | µ = 0.25 mm−1 |
c = 27.0427 (10) Å | T = 20 K |
V = 2560.70 (16) Å3 | Plate, colorless |
Z = 4 | 0.34 × 0.33 × 0.25 mm |
Oxford Sapphire CCD diffractometer | 7818 independent reflections |
Radiation source: fine-focus sealed tube | 6202 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.042 |
θ/2θ scans | θmax = 31.3°, θmin = 2.4° |
Absorption correction: numerical (CrysAlis RED; Oxford Diffraction, 2000) | h = −11→12 |
Tmin = 0.920, Tmax = 0.940 | k = −15→14 |
25421 measured reflections | l = −37→38 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.048 | H-atom parameters constrained |
wR(F2) = 0.124 | w = 1/[σ2(Fo2) + (0.0664P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.001 |
7818 reflections | Δρmax = 0.31 e Å−3 |
311 parameters | Δρmin = −0.28 e Å−3 |
0 restraints | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.01 (6) |
Experimental. The IR spectrum was recorded with a Perkin–Elmer Spectrum RX I spectrophotometer. 1H and 13C NMR spectra were taken in CDCl3 with a Varian Gemini 200 spectrometer. 1H NMR (300 MHz, CDCl3): δ 3.50–3.37 [m, 8H, 4CH2 (piperazine)], 3.34 [d, J = 14.7 Hz, 2H, 2CH (CH2S)], 2.76 [d, J = 14.7 Hz, 2H, 2 CH (CH2—S)], 2.53–2.32 [m, 4H, 4 CH (CH2)], 2.11 (t, J = 4.3 Hz, 2H, 2 CH), 2.10–1.99 [m, 2 H, 2 CH (CH2)], 1.94 [d, J = 18.3 Hz, 2H, 2CH (CH2)], 1,64 [ddd, J = 13.8, 9.5, 4.5 Hz, 2H, 2CH (CH2)], 1.44 [ddd, J = 12.6, 9.7, 3.5 Hz, 2H, 2CH (CH2)], 1.11 (s, 6H, 2CH3), 0.87 (s, 6H, 2CH3). 13C NMR (75.5 MHz, CDCl3): δ 214.82 (2CO), 58.11 (2 C), 47.98 (2 C), 45.80 (2CH2S), 45.56 (4CH2N piperazine), 42.72 (2CH), 42.49 (2CH2), 26.86 (2CH2), 25.07 (2CH2), 19.82 (2CH3), 19.70 (2CH3). IR (KBr): 2970, 1734, 1340, 1158, 1089, 946 cm-1. |
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 | ||
C1 | 0.45155 (19) | 0.96217 (18) | 0.03633 (6) | 0.0291 (3) | |
C2 | 0.5882 (3) | 0.8737 (2) | 0.04035 (9) | 0.0476 (5) | |
O1 | 0.5963 (3) | 0.7907 (2) | 0.06868 (9) | 0.0960 (9) | |
C3 | 0.7122 (3) | 0.9124 (2) | 0.00377 (9) | 0.0507 (6) | |
H3A | 0.7297 | 0.8518 | −0.0213 | 0.080* | |
H3B | 0.8114 | 0.9305 | 0.0201 | 0.080* | |
C4 | 0.6376 (2) | 1.02441 (18) | −0.01820 (7) | 0.0370 (4) | |
H4A | 0.7125 | 1.0796 | −0.0337 | 0.080* | |
C5 | 0.5067 (3) | 0.9805 (3) | −0.05218 (8) | 0.0614 (8) | |
H5A | 0.5446 | 0.9182 | −0.0741 | 0.080* | |
H5B | 0.4641 | 1.0455 | −0.0718 | 0.080* | |
C6 | 0.3810 (3) | 0.9311 (3) | −0.01571 (7) | 0.0601 (7) | |
H6A | 0.3681 | 0.8454 | −0.0196 | 0.080* | |
H6B | 0.2798 | 0.9699 | −0.0206 | 0.080* | |
C7 | 0.5451 (3) | 1.07752 (18) | 0.02588 (8) | 0.0429 (5) | |
C8 | 0.6540 (4) | 1.1097 (3) | 0.06983 (10) | 0.0795 (10) | |
H8A | 0.7327 | 1.1658 | 0.0591 | 0.080* | |
H8B | 0.7047 | 1.0386 | 0.0818 | 0.080* | |
H8C | 0.5923 | 1.1447 | 0.0959 | 0.080* | |
C9 | 0.4443 (5) | 1.1843 (2) | 0.01310 (14) | 0.0971 (13) | |
H9A | 0.5105 | 1.2481 | 0.0015 | 0.080* | |
H9B | 0.3878 | 1.2101 | 0.0420 | 0.080* | |
H9C | 0.3705 | 1.1627 | −0.0123 | 0.080* | |
C10 | 0.3450 (2) | 0.9585 (2) | 0.08180 (7) | 0.0390 (4) | |
H10A | 0.3710 | 1.0267 | 0.1024 | 0.080* | |
H10B | 0.3712 | 0.8872 | 0.1005 | 0.080* | |
S1 | 0.13803 (5) | 0.95912 (5) | 0.07196 (2) | 0.03607 (11) | |
O2 | 0.0931 (2) | 1.06726 (16) | 0.04861 (6) | 0.0561 (5) | |
O3 | 0.0961 (2) | 0.84750 (17) | 0.04990 (6) | 0.0582 (5) | |
N1 | 0.05717 (19) | 0.96053 (15) | 0.12699 (6) | 0.0349 (3) | |
C11 | 0.0578 (3) | 1.07274 (17) | 0.15558 (7) | 0.0404 (5) | |
H11A | 0.0447 | 1.1404 | 0.1335 | 0.080* | |
H11B | 0.1577 | 1.0816 | 0.1728 | 0.080* | |
C12 | −0.0771 (3) | 1.06899 (17) | 0.19276 (8) | 0.0402 (5) | |
H12A | −0.0749 | 1.1399 | 0.2134 | 0.080* | |
H12B | −0.1776 | 1.0665 | 0.1756 | 0.080* | |
N1A | −0.05787 (17) | 0.96087 (15) | 0.22346 (5) | 0.0330 (3) | |
C13 | 0.0744 (3) | 0.85370 (18) | 0.15783 (8) | 0.0431 (5) | |
H13A | 0.1747 | 0.8559 | 0.1751 | 0.080* | |
H13B | 0.0720 | 0.7826 | 0.1373 | 0.080* | |
C14 | −0.0594 (3) | 0.85022 (17) | 0.19464 (8) | 0.0415 (5) | |
H14A | −0.1594 | 0.8423 | 0.1774 | 0.080* | |
H14B | −0.0471 | 0.7820 | 0.2164 | 0.080* | |
S1A | −0.13407 (5) | 0.96032 (5) | 0.27911 (2) | 0.03266 (11) | |
O2A | −0.10310 (19) | 1.07576 (14) | 0.29984 (6) | 0.0484 (4) | |
O3A | −0.0741 (2) | 0.85669 (15) | 0.30350 (6) | 0.0536 (4) | |
C10A | −0.3407 (2) | 0.9411 (2) | 0.27109 (6) | 0.0354 (4) | |
H10C | −0.3768 | 0.9998 | 0.2473 | 0.080* | |
H10D | −0.3582 | 0.8628 | 0.2567 | 0.080* | |
C9A | −0.6708 (2) | 1.0663 (2) | 0.27505 (8) | 0.0434 (5) | |
H9D | −0.6145 | 1.0948 | 0.2466 | 0.080* | |
H9E | −0.7564 | 1.1197 | 0.2824 | 0.050* | |
H9F | −0.7119 | 0.9879 | 0.2684 | 0.050* | |
C8A | −0.4738 (3) | 1.18064 (19) | 0.32396 (8) | 0.0448 (5) | |
H8D | −0.4013 | 1.1776 | 0.3512 | 0.050* | |
H8E | −0.5499 | 1.2428 | 0.3296 | 0.050* | |
H8F | −0.4169 | 1.1970 | 0.2940 | 0.050* | |
C7A | −0.5588 (2) | 1.06051 (16) | 0.31927 (6) | 0.0309 (4) | |
C6A | −0.3676 (2) | 0.9519 (2) | 0.36954 (6) | 0.0395 (4) | |
H6C | −0.3382 | 0.8716 | 0.3796 | 0.080* | |
H6D | −0.2745 | 1.0025 | 0.3702 | 0.080* | |
C5A | −0.4991 (3) | 1.0027 (2) | 0.40339 (7) | 0.0454 (5) | |
H5C | −0.5249 | 0.9470 | 0.4297 | 0.080* | |
H5D | −0.4675 | 1.0784 | 0.4178 | 0.080* | |
C4A | −0.6385 (3) | 1.01896 (18) | 0.36804 (7) | 0.0370 (4) | |
H4B | −0.7214 | 1.0725 | 0.3803 | 0.080* | |
C3A | −0.6959 (3) | 0.8930 (2) | 0.35443 (8) | 0.0429 (5) | |
H3C | −0.7082 | 0.8434 | 0.3836 | 0.080* | |
H3D | −0.7953 | 0.8958 | 0.3366 | 0.080* | |
C2A | −0.5631 (3) | 0.84827 (18) | 0.32177 (7) | 0.0364 (4) | |
O1A | −0.5511 (2) | 0.75033 (15) | 0.30388 (7) | 0.0611 (5) | |
C1A | −0.44445 (19) | 0.95149 (17) | 0.31711 (6) | 0.0265 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0240 (7) | 0.0340 (8) | 0.0293 (8) | −0.0031 (8) | 0.0029 (6) | 0.0027 (8) |
C2 | 0.0479 (13) | 0.0450 (12) | 0.0499 (12) | 0.0089 (10) | 0.0124 (10) | 0.0141 (10) |
O1 | 0.1044 (19) | 0.0844 (15) | 0.0992 (16) | 0.0439 (14) | 0.0479 (14) | 0.0525 (13) |
C3 | 0.0392 (12) | 0.0600 (14) | 0.0529 (13) | 0.0086 (11) | 0.0121 (10) | 0.0067 (11) |
C4 | 0.0357 (9) | 0.0406 (11) | 0.0346 (9) | −0.0054 (9) | 0.0094 (8) | 0.0044 (8) |
C5 | 0.0446 (12) | 0.108 (2) | 0.0318 (10) | −0.0114 (14) | 0.0057 (9) | 0.0073 (12) |
C6 | 0.0423 (12) | 0.105 (2) | 0.0335 (10) | −0.0225 (14) | 0.0032 (9) | −0.0125 (12) |
C7 | 0.0511 (12) | 0.0298 (9) | 0.0476 (11) | −0.0053 (9) | 0.0197 (10) | −0.0007 (8) |
C8 | 0.078 (2) | 0.094 (2) | 0.0668 (17) | −0.0488 (19) | 0.0234 (16) | −0.0436 (16) |
C9 | 0.116 (3) | 0.0449 (16) | 0.130 (3) | 0.0264 (18) | 0.068 (3) | 0.0339 (17) |
C10 | 0.0272 (8) | 0.0576 (12) | 0.0323 (8) | −0.0019 (10) | 0.0042 (7) | 0.0095 (9) |
S1 | 0.0256 (2) | 0.0472 (3) | 0.0354 (2) | 0.0007 (2) | 0.00547 (17) | −0.0005 (2) |
O2 | 0.0509 (10) | 0.0719 (12) | 0.0456 (8) | 0.0209 (9) | 0.0055 (7) | 0.0175 (8) |
O3 | 0.0491 (10) | 0.0711 (12) | 0.0544 (10) | −0.0173 (9) | 0.0145 (8) | −0.0242 (8) |
N1 | 0.0351 (8) | 0.0311 (7) | 0.0386 (8) | 0.0027 (8) | 0.0136 (6) | 0.0003 (7) |
C11 | 0.0498 (12) | 0.0295 (10) | 0.0420 (10) | −0.0035 (9) | 0.0167 (9) | 0.0011 (8) |
C12 | 0.0463 (11) | 0.0301 (10) | 0.0441 (10) | 0.0061 (8) | 0.0153 (9) | 0.0008 (8) |
N1A | 0.0305 (7) | 0.0294 (7) | 0.0392 (8) | 0.0017 (7) | 0.0138 (6) | 0.0002 (7) |
C13 | 0.0478 (12) | 0.0318 (10) | 0.0496 (12) | 0.0066 (9) | 0.0239 (10) | 0.0020 (8) |
C14 | 0.0450 (12) | 0.0299 (10) | 0.0495 (11) | −0.0041 (9) | 0.0226 (10) | −0.0010 (8) |
S1A | 0.02255 (18) | 0.0411 (2) | 0.0344 (2) | −0.0011 (2) | 0.00446 (17) | −0.00071 (19) |
O2A | 0.0488 (9) | 0.0517 (9) | 0.0447 (8) | −0.0173 (7) | 0.0090 (7) | −0.0147 (7) |
O3A | 0.0435 (9) | 0.0662 (11) | 0.0513 (9) | 0.0164 (8) | 0.0088 (7) | 0.0190 (8) |
C10A | 0.0224 (8) | 0.0551 (12) | 0.0288 (8) | −0.0027 (8) | 0.0042 (6) | −0.0083 (8) |
C9A | 0.0328 (10) | 0.0480 (13) | 0.0495 (11) | 0.0054 (9) | −0.0049 (8) | 0.0114 (9) |
C8A | 0.0566 (14) | 0.0304 (10) | 0.0474 (12) | −0.0011 (9) | 0.0059 (10) | −0.0016 (8) |
C7A | 0.0279 (8) | 0.0336 (10) | 0.0312 (8) | 0.0009 (8) | 0.0027 (7) | 0.0039 (7) |
C6A | 0.0353 (9) | 0.0582 (12) | 0.0249 (7) | 0.0085 (11) | −0.0017 (7) | 0.0001 (8) |
C5A | 0.0494 (13) | 0.0600 (13) | 0.0267 (9) | 0.0085 (10) | 0.0074 (8) | 0.0002 (8) |
C4A | 0.0329 (9) | 0.0417 (11) | 0.0363 (9) | 0.0081 (9) | 0.0128 (8) | 0.0027 (7) |
C3A | 0.0350 (10) | 0.0456 (12) | 0.0482 (12) | 0.0002 (9) | 0.0133 (9) | 0.0091 (10) |
C2A | 0.0353 (10) | 0.0372 (10) | 0.0367 (10) | −0.0018 (9) | 0.0053 (8) | 0.0022 (8) |
O1A | 0.0711 (12) | 0.0425 (9) | 0.0698 (11) | −0.0105 (9) | 0.0214 (10) | −0.0152 (8) |
C1A | 0.0221 (7) | 0.0338 (8) | 0.0237 (7) | −0.0009 (8) | 0.0027 (5) | −0.0003 (7) |
C1—C10 | 1.526 (2) | C12—H12B | 0.9700 |
C1—C2 | 1.526 (3) | N1A—C14 | 1.462 (2) |
C1—C7 | 1.540 (3) | N1A—S1A | 1.637 (1) |
C1—C6 | 1.568 (3) | C13—C14 | 1.509 (3) |
C2—O1 | 1.206 (3) | C13—H13A | 0.9700 |
C2—C3 | 1.506 (3) | C13—H13B | 0.9700 |
C3—C4 | 1.524 (3) | C14—H14A | 0.9700 |
C3—H3A | 0.9700 | C14—H14B | 0.9700 |
C3—H3B | 0.9700 | S1A—O3A | 1.427 (2) |
C4—C5 | 1.521 (3) | S1A—O2A | 1.432 (2) |
C4—C7 | 1.545 (3) | S1A—C10A | 1.777 (2) |
C4—H4A | 0.9800 | C10A—C1A | 1.528 (2) |
C5—C6 | 1.553 (3) | C10A—H10C | 0.9700 |
C5—H5A | 0.9700 | C10A—H10D | 0.9700 |
C5—H5B | 0.9700 | C9A—C7A | 1.528 (3) |
C6—H6A | 0.9700 | C9A—H9D | 0.9600 |
C6—H6B | 0.9700 | C9A—H9E | 0.9600 |
C7—C9 | 1.508 (4) | C9A—H9F | 0.9600 |
C7—C8 | 1.547 (4) | C8A—C7A | 1.529 (3) |
C8—H8A | 0.9600 | C8A—H8D | 0.9600 |
C8—H8B | 0.9600 | C8A—H8E | 0.9600 |
C8—H8C | 0.9600 | C8A—H8F | 0.9600 |
C9—H9A | 0.9600 | C7A—C4A | 1.553 (2) |
C9—H9B | 0.9600 | C7A—C1A | 1.558 (3) |
C9—H9C | 0.9600 | C6A—C5A | 1.549 (3) |
C10—S1 | 1.773 (2) | C6A—C1A | 1.560 (2) |
C10—H10A | 0.9700 | C6A—H6C | 0.9700 |
C10—H10B | 0.9700 | C6A—H6D | 0.9700 |
S1—O2 | 1.416 (2) | C5A—C4A | 1.530 (3) |
S1—O3 | 1.428 (2) | C5A—H5C | 0.9700 |
S1—N1 | 1.638 (2) | C5A—H5D | 0.9700 |
N1—C13 | 1.464 (2) | C4A—C3A | 1.534 (3) |
N1—C11 | 1.474 (2) | C4A—H4B | 0.9800 |
C11—C12 | 1.523 (3) | C3A—C2A | 1.515 (3) |
C11—H11A | 0.9700 | C3A—H3C | 0.9700 |
C11—H11B | 0.9700 | C3A—H3D | 0.9700 |
C12—N1A | 1.476 (2) | C2A—O1A | 1.202 (2) |
C12—H12A | 0.9700 | C2A—C1A | 1.536 (3) |
C10—C1—C2 | 111.9 (2) | C14—N1A—C12 | 113.1 (2) |
C10—C1—C7 | 118.4 (2) | C14—N1A—S1A | 118.9 (1) |
C2—C1—C7 | 99.6 (2) | C12—N1A—S1A | 118.5 (1) |
C10—C1—C6 | 119.5 (2) | N1—C13—C14 | 108.8 (2) |
C2—C1—C6 | 102.1 (2) | N1—C13—H13A | 109.9 |
C7—C1—C6 | 102.5 (2) | C14—C13—H13A | 109.9 |
O1—C2—C3 | 126.8 (2) | N1—C13—H13B | 109.9 |
O1—C2—C1 | 126.0 (2) | C14—C13—H13B | 109.9 |
C3—C2—C1 | 107.2 (2) | H13A—C13—H13B | 108.3 |
C2—C3—C4 | 101.7 (2) | N1A—C14—C13 | 108.8 (2) |
C2—C3—H3A | 111.4 | N1A—C14—H14A | 109.9 |
C4—C3—H3A | 111.4 | C13—C14—H14A | 109.9 |
C2—C3—H3B | 111.4 | N1A—C14—H14B | 109.9 |
C4—C3—H3B | 111.4 | C13—C14—H14B | 109.9 |
H3A—C3—H3B | 109.3 | H14A—C14—H14B | 108.3 |
C5—C4—C3 | 105.8 (2) | O3A—S1A—O2A | 119.1 (1) |
C5—C4—C7 | 102.8 (2) | O3A—S1A—N1A | 106.74 (9) |
C3—C4—C7 | 103.0 (2) | O2A—S1A—N1A | 106.51 (9) |
C5—C4—H4A | 114.6 | O3A—S1A—C10A | 108.0 (1) |
C3—C4—H4A | 114.6 | O2A—S1A—C10A | 109.7 (1) |
C7—C4—H4A | 114.6 | N1A—S1A—C10A | 106.06 (8) |
C4—C5—C6 | 103.3 (2) | C1A—C10A—S1A | 117.2 (1) |
C4—C5—H5A | 111.1 | C1A—C10A—H10C | 108.0 |
C6—C5—H5A | 111.1 | S1A—C10A—H10C | 108.0 |
C4—C5—H5B | 111.1 | C1A—C10A—H10D | 108.0 |
C6—C5—H5B | 111.1 | S1A—C10A—H10D | 108.0 |
H5A—C5—H5B | 109.1 | H10C—C10A—H10D | 107.2 |
C5—C6—C1 | 103.3 (2) | C7A—C9A—H9D | 109.5 |
C5—C6—H6A | 111.1 | C7A—C9A—H9E | 109.5 |
C1—C6—H6A | 111.1 | H9D—C9A—H9E | 109.5 |
C5—C6—H6B | 111.1 | C7A—C9A—H9F | 109.5 |
C1—C6—H6B | 111.1 | H9D—C9A—H9F | 109.5 |
H6A—C6—H6B | 109.1 | H9E—C9A—H9F | 109.5 |
C9—C7—C1 | 114.5 (2) | C7A—C8A—H8D | 109.5 |
C9—C7—C4 | 114.5 (2) | C7A—C8A—H8E | 109.5 |
C1—C7—C4 | 94.6 (2) | H8D—C8A—H8E | 109.5 |
C9—C7—C8 | 109.2 (3) | C7A—C8A—H8F | 109.5 |
C1—C7—C8 | 111.1 (2) | H8D—C8A—H8F | 109.5 |
C4—C7—C8 | 112.3 (2) | H8E—C8A—H8F | 109.5 |
C7—C8—H8A | 109.5 | C9A—C7A—C8A | 108.7 (2) |
C7—C8—H8B | 109.5 | C9A—C7A—C4A | 114.1 (2) |
H8A—C8—H8B | 109.5 | C8A—C7A—C4A | 113.4 (2) |
C7—C8—H8C | 109.5 | C9A—C7A—C1A | 112.9 (2) |
H8A—C8—H8C | 109.5 | C8A—C7A—C1A | 113.5 (2) |
H8B—C8—H8C | 109.5 | C4A—C7A—C1A | 93.9 (1) |
C7—C9—H9A | 109.5 | C5A—C6A—C1A | 103.8 (2) |
C7—C9—H9B | 109.5 | C5A—C6A—H6C | 111.0 |
H9A—C9—H9B | 109.5 | C1A—C6A—H6C | 111.0 |
C7—C9—H9C | 109.5 | C5A—C6A—H6D | 111.0 |
H9A—C9—H9C | 109.5 | C1A—C6A—H6D | 111.0 |
H9B—C9—H9C | 109.5 | H6C—C6A—H6D | 109.0 |
C1—C10—S1 | 117.6 (1) | C4A—C5A—C6A | 103.2 (2) |
C1—C10—H10A | 107.9 | C4A—C5A—H5C | 111.1 |
S1—C10—H10A | 107.9 | C6A—C5A—H5C | 111.1 |
C1—C10—H10B | 107.9 | C4A—C5A—H5D | 111.1 |
S1—C10—H10B | 107.9 | C6A—C5A—H5D | 111.1 |
H10A—C10—H10B | 107.2 | H5C—C5A—H5D | 109.1 |
O2—S1—O3 | 119.6 (1) | C5A—C4A—C3A | 106.6 (2) |
O2—S1—N1 | 106.55 (9) | C5A—C4A—C7A | 103.3 (2) |
O3—S1—N1 | 106.5 (1) | C3A—C4A—C7A | 102.1 (2) |
O2—S1—C10 | 109.6 (1) | C5A—C4A—H4B | 114.5 |
O3—S1—C10 | 107.7 (1) | C3A—C4A—H4B | 114.5 |
N1—S1—C10 | 106.09 (9) | C7A—C4A—H4B | 114.5 |
C13—N1—C11 | 113.3 (2) | C2A—C3A—C4A | 102.0 (2) |
C13—N1—S1 | 117.9 (1) | C2A—C3A—H3C | 111.4 |
C11—N1—S1 | 118.9 (1) | C4A—C3A—H3C | 111.4 |
N1—C11—C12 | 108.7 (2) | C2A—C3A—H3D | 111.4 |
N1—C11—H11A | 110.0 | C4A—C3A—H3D | 111.4 |
C12—C11—H11A | 110.0 | H3C—C3A—H3D | 109.2 |
N1—C11—H11B | 110.0 | O1A—C2A—C3A | 126.8 (2) |
C12—C11—H11B | 110.0 | O1A—C2A—C1A | 126.6 (2) |
H11A—C11—H11B | 108.3 | C3A—C2A—C1A | 106.6 (2) |
N1A—C12—C11 | 108.2 (2) | C10A—C1A—C2A | 112.7 (2) |
N1A—C12—H12A | 110.1 | C10A—C1A—C7A | 116.6 (2) |
C11—C12—H12A | 110.1 | C2A—C1A—C7A | 100.3 (1) |
N1A—C12—H12B | 110.1 | C10A—C1A—C6A | 120.1 (1) |
C11—C12—H12B | 110.1 | C2A—C1A—C6A | 101.6 (2) |
H12A—C12—H12B | 108.4 | C7A—C1A—C6A | 102.9 (1) |
C10—C1—C2—O1 | 16.8 (4) | C11—N1—C13—C14 | 58.9 (2) |
C7—C1—C2—O1 | 142.7 (3) | S1—N1—C13—C14 | −155.67 (15) |
C6—C1—C2—O1 | −112.2 (3) | C12—N1A—C14—C13 | 59.9 (2) |
C10—C1—C2—C3 | −161.22 (19) | S1A—N1A—C14—C13 | −154.26 (15) |
C7—C1—C2—C3 | −35.3 (2) | N1—C13—C14—N1A | −56.8 (3) |
C6—C1—C2—C3 | 69.8 (2) | C14—N1A—S1A—O3A | 46.55 (19) |
O1—C2—C3—C4 | −176.7 (3) | C12—N1A—S1A—O3A | −169.46 (16) |
C1—C2—C3—C4 | 1.3 (2) | C14—N1A—S1A—O2A | 174.77 (16) |
C2—C3—C4—C5 | −74.0 (2) | C12—N1A—S1A—O2A | −41.24 (18) |
C2—C3—C4—C7 | 33.5 (2) | C14—N1A—S1A—C10A | −68.38 (18) |
C3—C4—C5—C6 | 70.1 (3) | C12—N1A—S1A—C10A | 75.61 (17) |
C7—C4—C5—C6 | −37.6 (3) | O3A—S1A—C10A—C1A | 72.71 (18) |
C4—C5—C6—C1 | 4.2 (3) | O2A—S1A—C10A—C1A | −58.53 (19) |
C10—C1—C6—C5 | 163.8 (2) | N1A—S1A—C10A—C1A | −173.20 (15) |
C2—C1—C6—C5 | −72.2 (2) | C1A—C6A—C5A—C4A | 3.1 (2) |
C7—C1—C6—C5 | 30.6 (3) | C6A—C5A—C4A—C3A | 70.2 (2) |
C10—C1—C7—C9 | −66.0 (3) | C6A—C5A—C4A—C7A | −36.9 (2) |
C2—C1—C7—C9 | 172.6 (2) | C9A—C7A—C4A—C5A | 171.66 (17) |
C6—C1—C7—C9 | 67.8 (3) | C8A—C7A—C4A—C5A | −63.2 (2) |
C10—C1—C7—C4 | 174.38 (16) | C1A—C7A—C4A—C5A | 54.42 (17) |
C2—C1—C7—C4 | 52.99 (18) | C9A—C7A—C4A—C3A | 61.2 (2) |
C6—C1—C7—C4 | −51.8 (2) | C8A—C7A—C4A—C3A | −173.76 (17) |
C10—C1—C7—C8 | 58.3 (3) | C1A—C7A—C4A—C3A | −56.09 (17) |
C2—C1—C7—C8 | −63.1 (2) | C5A—C4A—C3A—C2A | −70.88 (19) |
C6—C1—C7—C8 | −167.9 (2) | C7A—C4A—C3A—C2A | 37.17 (19) |
C5—C4—C7—C9 | −64.2 (3) | C4A—C3A—C2A—O1A | 176.1 (2) |
C3—C4—C7—C9 | −174.0 (2) | C4A—C3A—C2A—C1A | −2.4 (2) |
C5—C4—C7—C1 | 55.4 (2) | S1A—C10A—C1A—C2A | −132.03 (16) |
C3—C4—C7—C1 | −54.42 (19) | S1A—C10A—C1A—C7A | 112.78 (16) |
C5—C4—C7—C8 | 170.5 (2) | S1A—C10A—C1A—C6A | −12.5 (3) |
C3—C4—C7—C8 | 60.7 (2) | O1A—C2A—C1A—C10A | 24.0 (3) |
C2—C1—C10—S1 | −135.85 (18) | C3A—C2A—C1A—C10A | −157.48 (16) |
C7—C1—C10—S1 | 109.29 (19) | O1A—C2A—C1A—C7A | 148.7 (2) |
C6—C1—C10—S1 | −16.7 (3) | C3A—C2A—C1A—C7A | −32.81 (18) |
C1—C10—S1—O2 | −63.0 (2) | O1A—C2A—C1A—C6A | −105.7 (2) |
C1—C10—S1—O3 | 68.64 (19) | C3A—C2A—C1A—C6A | 72.76 (19) |
C1—C10—S1—N1 | −177.63 (16) | C9A—C7A—C1A—C10A | 56.7 (2) |
O2—S1—N1—C13 | 175.15 (17) | C8A—C7A—C1A—C10A | −67.5 (2) |
O3—S1—N1—C13 | 46.49 (19) | C4A—C7A—C1A—C10A | 174.91 (15) |
C10—S1—N1—C13 | −68.10 (19) | C9A—C7A—C1A—C2A | −65.23 (17) |
O2—S1—N1—C11 | −41.40 (18) | C8A—C7A—C1A—C2A | 170.56 (16) |
O3—S1—N1—C11 | −170.07 (16) | C4A—C7A—C1A—C2A | 52.95 (15) |
C10—S1—N1—C11 | 75.34 (18) | C9A—C7A—C1A—C6A | −169.74 (15) |
C13—N1—C11—C12 | −58.8 (2) | C8A—C7A—C1A—C6A | 66.06 (19) |
S1—N1—C11—C12 | 156.15 (15) | C4A—C7A—C1A—C6A | −51.55 (16) |
N1—C11—C12—N1A | 56.1 (2) | C5A—C6A—C1A—C10A | 162.83 (19) |
C11—C12—N1A—C14 | −59.5 (2) | C5A—C6A—C1A—C2A | −72.17 (19) |
C11—C12—N1A—S1A | 154.55 (14) | C5A—C6A—C1A—C7A | 31.3 (2) |