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
Key indicators
- Single-crystal X-ray study
- T = 20 K
- Mean (C-C) = 0.003 Å
- R factor = 0.048
- wR factor = 0.124
- Data-to-parameter ratio = 25.1
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.95 PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.66 Ratio
Alert level C CELLK01_ALERT_1_C Check that the cell measurement temperature is in Kelvin. Value of measurement temperature given = 20.000 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT230_ALERT_2_C Hirshfeld Test Diff for C1A - C2A .. 5.16 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C7 PLAT245_ALERT_2_C U(iso) H9A Smaller than U(eq) C9 by ... 0.02 AngSq PLAT245_ALERT_2_C U(iso) H9B Smaller than U(eq) C9 by ... 0.02 AngSq PLAT245_ALERT_2_C U(iso) H9C Smaller than U(eq) C9 by ... 0.02 AngSq
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 31.25 From the CIF: _reflns_number_total 7818 Count of symmetry unique reflns 4693 Completeness (_total/calc) 166.59% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 3125 Fraction of Friedel pairs measured 0.666 Are heavy atom types Z>Si present yes PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1A = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4A = . R
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 5 ALERT level G = General alerts; check 6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 7 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
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) |
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