Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804007366/na6310sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804007366/na6310Isup2.hkl |
CCDC reference: 239129
Data collection: XSCANS (Siemens, 1989); cell refinement: XSCANS; data reduction: XPREPW (Bruker, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XPW (Bruker, 1997) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: PARST97 (Nardelli, 1995) and WinGX (PC Version 1.6.4.05; Farrugia, 1999).
C24H34O6S | Z = 1 |
Mr = 450.57 | F(000) = 242 |
Triclinic, P1 | Dx = 1.266 Mg m−3 |
Hall symbol: P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.8037 (6) Å | Cell parameters from 62 reflections |
b = 7.7391 (8) Å | θ = 5.1–20.0° |
c = 11.9131 (9) Å | µ = 0.17 mm−1 |
α = 84.539 (8)° | T = 298 K |
β = 74.277 (6)° | Prismatic, colourless |
γ = 78.323 (7)° | 0.46 × 0.32 × 0.28 mm |
V = 590.77 (9) Å3 |
Bruker P4 diffractometer | θmax = 25°, θmin = 2.7° |
2θ/ω scans | h = −8→1 |
2643 measured reflections | k = −9→9 |
2642 independent reflections | l = −14→13 |
2244 reflections with I > 2σ(I) | 3 standard reflections every 197 reflections |
Rint = 0.008 | intensity decay: 1% |
Refinement on F2 | w = 1/[σ2(Fo2) + (0.0439P)2 + 0.1716P] where P = (Fo2 + 2Fc2)/3 |
Least-squares matrix: full | (Δ/σ)max < 0.001 |
R[F2 > 2σ(F2)] = 0.042 | Δρmax = 0.19 e Å−3 |
wR(F2) = 0.101 | Δρmin = −0.23 e Å−3 |
S = 1.02 | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
2642 reflections | Extinction coefficient: 0.019 (4) |
281 parameters | Absolute structure: Flack (1983) |
3 restraints | Absolute structure parameter: 0.05 (10) |
H-atom parameters constrained |
Experimental. Selected 1H NMR absorptions: δ 4.04 (dd, J2',3' = 6.5 and 4.6 Hz, H-2'), 3.81 and 3.79 (two s, 2 × OMe), 2.91 and 2.83 (AB system, J10'A,10'B = 13.2 Hz, H2–10'), 1.10 (s, H3–8'), 0.86 (s, H3–9'). Dimethyl (8aS,SS)-3,5,6,7,8,8a-hexahydro-4-[(1S)-isoborneol-10-sulfinyl]- 1,2-naphthalenedicarboxylate was eluted as a solid (m.p. 458–460 K, 48% yield). Selected 1H NMR absorptions: δ 4.12 (t, J2',3' = 5.6 Hz, H-2'), 3.80 and 3.78 (two s, 2 × OMe), 2.90 and 2.87 (AB system, J10'A,10'B = 13.2 Hz, H2–10'), 1.12 (s, H3–8'), 0.87 (s, H3–9'). Compound (I) was recrystallized from Et2O–petrol (2:1 v/v) (m.p. 473–475 K). |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
S | 0.52964 (14) | 0.40561 (11) | 0.67238 (8) | 0.0474 (3) | |
O1 | 0.3130 (5) | 0.4133 (4) | 0.7488 (2) | 0.0622 (8) | |
O2 | 0.9770 (7) | 0.3049 (7) | 0.7244 (3) | 0.1277 (19) | |
H2A | 1.073 | 0.3332 | 0.7433 | 0.153* | |
O3 | 0.5776 (7) | 0.4510 (6) | 0.0915 (3) | 0.0980 (13) | |
O4 | 0.2448 (7) | 0.5583 (5) | 0.1644 (3) | 0.0976 (14) | |
O5 | 0.0694 (7) | 0.1863 (5) | 0.4181 (3) | 0.0973 (14) | |
O6 | 0.2530 (6) | 0.2032 (5) | 0.2363 (2) | 0.0811 (11) | |
C1 | 0.4463 (7) | 0.4564 (5) | 0.2972 (3) | 0.0459 (10) | |
C2 | 0.3433 (6) | 0.3484 (5) | 0.3751 (3) | 0.0440 (9) | |
C3 | 0.3552 (8) | 0.3275 (6) | 0.4995 (3) | 0.0538 (11) | |
H3A | 0.3922 | 0.2028 | 0.5194 | 0.065* | |
H3B | 0.219 | 0.3712 | 0.5496 | 0.065* | |
C4 | 0.5098 (6) | 0.4231 (5) | 0.5236 (3) | 0.0444 (10) | |
C4A | 0.6207 (6) | 0.5240 (5) | 0.4458 (3) | 0.0458 (10) | |
C5 | 0.7766 (7) | 0.6214 (5) | 0.4672 (4) | 0.0560 (11) | |
H5A | 0.9122 | 0.5794 | 0.416 | 0.067* | |
H5B | 0.7861 | 0.5978 | 0.5472 | 0.067* | |
C6 | 0.7138 (9) | 0.8202 (5) | 0.4451 (4) | 0.0678 (13) | |
H6A | 0.5865 | 0.8648 | 0.5026 | 0.081* | |
H6B | 0.8215 | 0.8795 | 0.4534 | 0.081* | |
C7 | 0.6812 (9) | 0.8604 (6) | 0.3229 (4) | 0.0715 (14) | |
H7A | 0.6328 | 0.9862 | 0.3124 | 0.086* | |
H7B | 0.8124 | 0.8278 | 0.2654 | 0.086* | |
C8 | 0.5235 (9) | 0.7597 (5) | 0.3040 (4) | 0.0630 (12) | |
H8A | 0.5089 | 0.7844 | 0.225 | 0.076* | |
H8B | 0.3894 | 0.7994 | 0.3574 | 0.076* | |
C8A | 0.5916 (7) | 0.5582 (5) | 0.3240 (3) | 0.0483 (10) | |
H8AA | 0.7278 | 0.5229 | 0.2695 | 0.058* | |
C9 | 0.4335 (9) | 0.4838 (6) | 0.1728 (4) | 0.0621 (12) | |
C10 | 0.2133 (14) | 0.5824 (10) | 0.0476 (5) | 0.145 (3) | |
H10A | 0.0716 | 0.6366 | 0.0518 | 0.174* | 0.5 |
H10B | 0.2435 | 0.4697 | 0.0131 | 0.174* | 0.5 |
H10C | 0.3041 | 0.6569 | 0.0006 | 0.174* | 0.5 |
H10D | 0.3412 | 0.5389 | −0.0081 | 0.174* | 0.5 |
H10E | 0.1693 | 0.7057 | 0.0306 | 0.174* | 0.5 |
H10F | 0.1087 | 0.5186 | 0.0431 | 0.174* | 0.5 |
C11 | 0.2037 (7) | 0.2408 (5) | 0.3482 (3) | 0.0523 (11) | |
C12 | 0.1129 (10) | 0.1126 (8) | 0.2022 (5) | 0.0949 (19) | |
H12A | 0.1621 | 0.0913 | 0.1204 | 0.142* | |
H12B | −0.0235 | 0.1843 | 0.2179 | 0.142* | |
H12C | 0.1074 | 0.002 | 0.2459 | 0.142* | |
C1' | 0.7175 (7) | 0.1201 (5) | 0.7886 (3) | 0.0504 (10) | |
C2' | 0.8408 (8) | 0.2386 (8) | 0.8247 (4) | 0.0771 (15) | |
H2'A | 0.7436 | 0.3384 | 0.8655 | 0.092* | |
C3' | 0.9446 (10) | 0.1242 (14) | 0.9109 (5) | 0.135 (3) | |
H3'A | 0.9016 | 0.1757 | 0.9869 | 0.162* | |
H3'B | 1.0948 | 0.1067 | 0.8832 | 0.162* | |
C4' | 0.8661 (14) | −0.0492 (11) | 0.9156 (5) | 0.121 (3) | |
H4'A | 0.9509 | −0.1512 | 0.9459 | 0.146* | |
C5' | 0.6389 (11) | −0.0140 (8) | 0.9851 (4) | 0.097 (2) | |
H5'A | 0.6207 | 0.0459 | 1.0561 | 0.116* | |
H5'B | 0.584 | −0.1225 | 1.0046 | 0.116* | |
C6' | 0.5353 (8) | 0.1068 (7) | 0.8971 (4) | 0.0671 (13) | |
H6'A | 0.4303 | 0.0545 | 0.8788 | 0.081* | |
H6'B | 0.4718 | 0.2223 | 0.9281 | 0.081* | |
C7' | 0.8522 (12) | −0.0692 (8) | 0.7904 (4) | 0.105 (2) | |
C8' | 1.0677 (15) | −0.0880 (13) | 0.6994 (6) | 0.193 (6) | |
H8'1 | 1.1375 | 0.0037 | 0.7087 | 0.232* | 0.5 |
H8'2 | 1.0483 | −0.0781 | 0.622 | 0.232* | 0.5 |
H8'3 | 1.1501 | −0.2011 | 0.7113 | 0.232* | 0.5 |
H8'4 | 1.0864 | −0.1874 | 0.6526 | 0.232* | 0.5 |
H8'5 | 1.1756 | −0.1055 | 0.7394 | 0.232* | 0.5 |
H8'6 | 1.0738 | 0.0174 | 0.65 | 0.232* | 0.5 |
C9' | 0.738 (2) | −0.2134 (8) | 0.7772 (7) | 0.196 (6) | |
H9'1 | 0.7377 | −0.2164 | 0.697 | 0.235* | 0.5 |
H9'2 | 0.5981 | −0.1892 | 0.8246 | 0.235* | 0.5 |
H9'3 | 0.8078 | −0.3255 | 0.8017 | 0.235* | 0.5 |
H9'4 | 0.6914 | −0.271 | 0.8519 | 0.235* | 0.5 |
H9'5 | 0.831 | −0.2982 | 0.7243 | 0.235* | 0.5 |
H9'6 | 0.6213 | −0.1619 | 0.7472 | 0.235* | 0.5 |
C10' | 0.6603 (7) | 0.1771 (5) | 0.6741 (3) | 0.0489 (10) | |
H10G | 0.5703 | 0.1022 | 0.6617 | 0.059* | |
H10H | 0.7854 | 0.1615 | 0.6104 | 0.059* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S | 0.0594 (7) | 0.0463 (5) | 0.0439 (5) | −0.0154 (5) | −0.0243 (5) | 0.0063 (4) |
O1 | 0.055 (2) | 0.079 (2) | 0.0512 (15) | −0.0098 (17) | −0.0148 (15) | 0.0009 (13) |
O2 | 0.104 (3) | 0.257 (6) | 0.0535 (19) | −0.115 (4) | −0.020 (2) | 0.017 (3) |
O3 | 0.104 (3) | 0.149 (4) | 0.0428 (18) | −0.044 (3) | −0.002 (2) | −0.0163 (19) |
O4 | 0.119 (4) | 0.109 (3) | 0.060 (2) | 0.023 (3) | −0.052 (2) | 0.0072 (18) |
O5 | 0.112 (3) | 0.140 (3) | 0.0547 (19) | −0.084 (3) | 0.000 (2) | −0.0114 (19) |
O6 | 0.095 (3) | 0.125 (3) | 0.0466 (17) | −0.062 (2) | −0.0293 (18) | 0.0048 (17) |
C1 | 0.051 (3) | 0.046 (2) | 0.0394 (19) | −0.004 (2) | −0.0140 (19) | 0.0032 (16) |
C2 | 0.049 (2) | 0.045 (2) | 0.0384 (19) | −0.0080 (19) | −0.0130 (18) | 0.0020 (16) |
C3 | 0.069 (3) | 0.059 (2) | 0.045 (2) | −0.029 (2) | −0.027 (2) | 0.0125 (18) |
C4 | 0.056 (3) | 0.042 (2) | 0.0402 (19) | −0.010 (2) | −0.022 (2) | 0.0081 (16) |
C4A | 0.048 (3) | 0.0403 (19) | 0.051 (2) | −0.0094 (19) | −0.019 (2) | 0.0086 (17) |
C5 | 0.059 (3) | 0.053 (2) | 0.064 (3) | −0.021 (2) | −0.026 (2) | 0.0117 (19) |
C6 | 0.086 (4) | 0.054 (2) | 0.071 (3) | −0.032 (3) | −0.022 (3) | 0.007 (2) |
C7 | 0.097 (4) | 0.051 (2) | 0.072 (3) | −0.031 (3) | −0.025 (3) | 0.017 (2) |
C8 | 0.083 (3) | 0.049 (2) | 0.060 (3) | −0.016 (2) | −0.028 (3) | 0.0189 (19) |
C8A | 0.052 (3) | 0.044 (2) | 0.045 (2) | −0.0089 (19) | −0.010 (2) | 0.0091 (16) |
C9 | 0.084 (4) | 0.057 (2) | 0.044 (2) | −0.019 (3) | −0.014 (3) | 0.0074 (19) |
C10 | 0.206 (10) | 0.152 (6) | 0.090 (5) | 0.013 (6) | −0.104 (6) | 0.022 (4) |
C11 | 0.060 (3) | 0.060 (2) | 0.043 (2) | −0.017 (2) | −0.021 (2) | 0.0068 (18) |
C12 | 0.107 (5) | 0.134 (5) | 0.074 (3) | −0.061 (4) | −0.048 (3) | 0.000 (3) |
C1' | 0.054 (3) | 0.059 (2) | 0.040 (2) | −0.009 (2) | −0.019 (2) | 0.0092 (17) |
C2' | 0.065 (3) | 0.141 (5) | 0.038 (2) | −0.047 (3) | −0.019 (2) | 0.008 (2) |
C3' | 0.064 (4) | 0.284 (11) | 0.062 (4) | −0.032 (6) | −0.037 (3) | 0.023 (5) |
C4' | 0.121 (6) | 0.154 (6) | 0.063 (3) | 0.047 (5) | −0.044 (4) | 0.027 (4) |
C5' | 0.140 (6) | 0.104 (4) | 0.055 (3) | −0.038 (5) | −0.040 (4) | 0.033 (3) |
C6' | 0.063 (3) | 0.090 (3) | 0.052 (2) | −0.029 (3) | −0.018 (2) | 0.019 (2) |
C7' | 0.144 (6) | 0.085 (4) | 0.063 (3) | 0.038 (4) | −0.038 (4) | 0.008 (3) |
C8' | 0.177 (10) | 0.225 (9) | 0.086 (5) | 0.140 (8) | −0.015 (5) | 0.010 (5) |
C9' | 0.415 (19) | 0.050 (3) | 0.125 (6) | −0.001 (6) | −0.111 (8) | 0.012 (3) |
C10' | 0.063 (3) | 0.044 (2) | 0.043 (2) | −0.009 (2) | −0.022 (2) | 0.0014 (16) |
S—O1 | 1.501 (3) | C10—H10E | 0.96 |
S—C4 | 1.804 (3) | C10—H10F | 0.96 |
S—C10' | 1.812 (4) | C12—H12A | 0.96 |
O2—C2' | 1.423 (5) | C12—H12B | 0.96 |
O2—H2A | 0.82 | C12—H12C | 0.96 |
O3—C9 | 1.182 (6) | C1'—C2' | 1.520 (6) |
O4—C9 | 1.323 (6) | C1'—C10' | 1.520 (5) |
O4—C10 | 1.453 (6) | C1'—C6' | 1.542 (6) |
O5—C11 | 1.176 (5) | C1'—C7' | 1.564 (6) |
O6—C11 | 1.329 (5) | C2'—C3' | 1.519 (8) |
O6—C12 | 1.449 (6) | C2'—H2'A | 0.98 |
C1—C2 | 1.337 (5) | C3'—C4' | 1.533 (12) |
C1—C8A | 1.495 (6) | C3'—H3'A | 0.97 |
C1—C9 | 1.500 (5) | C3'—H3'B | 0.97 |
C2—C11 | 1.495 (6) | C4'—C5' | 1.526 (10) |
C2—C3 | 1.498 (5) | C4'—C7' | 1.544 (8) |
C3—C4 | 1.502 (6) | C4'—H4'A | 0.98 |
C3—H3A | 0.97 | C5'—C6' | 1.554 (7) |
C3—H3B | 0.97 | C5'—H5'A | 0.97 |
C4—C4A | 1.326 (5) | C5'—H5'B | 0.97 |
C4A—C5 | 1.505 (6) | C6'—H6'A | 0.97 |
C4A—C8A | 1.509 (5) | C6'—H6'B | 0.97 |
C5—C6 | 1.528 (6) | C7'—C9' | 1.523 (11) |
C5—H5A | 0.97 | C7'—C8' | 1.558 (10) |
C5—H5B | 0.97 | C8'—H8'1 | 0.96 |
C6—C7 | 1.525 (6) | C8'—H8'2 | 0.96 |
C6—H6A | 0.97 | C8'—H8'3 | 0.96 |
C6—H6B | 0.97 | C8'—H8'4 | 0.96 |
C7—C8 | 1.521 (7) | C8'—H8'5 | 0.96 |
C7—H7A | 0.97 | C8'—H8'6 | 0.96 |
C7—H7B | 0.97 | C9'—H9'1 | 0.96 |
C8—C8A | 1.549 (5) | C9'—H9'2 | 0.96 |
C8—H8A | 0.97 | C9'—H9'3 | 0.96 |
C8—H8B | 0.97 | C9'—H9'4 | 0.96 |
C8A—H8AA | 0.98 | C9'—H9'5 | 0.96 |
C10—H10A | 0.96 | C9'—H9'6 | 0.96 |
C10—H10B | 0.96 | C10'—H10G | 0.97 |
C10—H10C | 0.96 | C10'—H10H | 0.97 |
C10—H10D | 0.96 | ||
O1—S—C4 | 106.58 (18) | C10'—C1'—C6' | 116.3 (4) |
O1—S—C10' | 107.13 (18) | C2'—C1'—C7' | 104.4 (5) |
C4—S—C10' | 97.93 (16) | C10'—C1'—C7' | 114.5 (3) |
C2'—O2—H2A | 109.5 | C6'—C1'—C7' | 101.4 (4) |
C9—O4—C10 | 116.6 (5) | O2—C2'—C3' | 115.8 (5) |
C11—O6—C12 | 115.9 (4) | O2—C2'—C1' | 110.2 (4) |
C2—C1—C8A | 123.4 (3) | C3'—C2'—C1' | 104.4 (5) |
C2—C1—C9 | 123.7 (4) | O2—C2'—H2'A | 108.8 |
C8A—C1—C9 | 112.9 (3) | C3'—C2'—H2'A | 108.8 |
C1—C2—C11 | 124.0 (3) | C1'—C2'—H2'A | 108.8 |
C1—C2—C3 | 122.4 (4) | C2'—C3'—C4' | 102.3 (5) |
C11—C2—C3 | 113.7 (3) | C2'—C3'—H3'A | 111.3 |
C2—C3—C4 | 113.4 (3) | C4'—C3'—H3'A | 111.3 |
C2—C3—H3A | 108.9 | C2'—C3'—H3'B | 111.3 |
C4—C3—H3A | 108.9 | C4'—C3'—H3'B | 111.3 |
C2—C3—H3B | 108.9 | H3'A—C3'—H3'B | 109.2 |
C4—C3—H3B | 108.9 | C5'—C4'—C3' | 106.1 (6) |
H3A—C3—H3B | 107.7 | C5'—C4'—C7' | 103.1 (6) |
C4A—C4—C3 | 124.8 (3) | C3'—C4'—C7' | 105.2 (5) |
C4A—C4—S | 119.3 (3) | C5'—C4'—H4'A | 113.8 |
C3—C4—S | 115.8 (3) | C3'—C4'—H4'A | 113.8 |
C4—C4A—C5 | 126.0 (4) | C7'—C4'—H4'A | 113.8 |
C4—C4A—C8A | 121.1 (4) | C4'—C5'—C6' | 101.5 (4) |
C5—C4A—C8A | 112.8 (3) | C4'—C5'—H5'A | 111.5 |
C4A—C5—C6 | 110.9 (4) | C6'—C5'—H5'A | 111.5 |
C4A—C5—H5A | 109.5 | C4'—C5'—H5'B | 111.5 |
C6—C5—H5A | 109.5 | C6'—C5'—H5'B | 111.5 |
C4A—C5—H5B | 109.5 | H5'A—C5'—H5'B | 109.3 |
C6—C5—H5B | 109.5 | C1'—C6'—C5' | 103.7 (4) |
H5A—C5—H5B | 108.1 | C1'—C6'—H6'A | 111 |
C7—C6—C5 | 110.7 (3) | C5'—C6'—H6'A | 111 |
C7—C6—H6A | 109.5 | C1'—C6'—H6'B | 111 |
C5—C6—H6A | 109.5 | C5'—C6'—H6'B | 111 |
C7—C6—H6B | 109.5 | H6'A—C6'—H6'B | 109 |
C5—C6—H6B | 109.5 | C9'—C7'—C4' | 115.3 (6) |
H6A—C6—H6B | 108.1 | C9'—C7'—C8' | 110.4 (7) |
C8—C7—C6 | 111.0 (4) | C4'—C7'—C8' | 112.7 (7) |
C8—C7—H7A | 109.4 | C9'—C7'—C1' | 112.7 (6) |
C6—C7—H7A | 109.4 | C4'—C7'—C1' | 91.3 (4) |
C8—C7—H7B | 109.4 | C8'—C7'—C1' | 113.2 (5) |
C6—C7—H7B | 109.4 | C7'—C8'—H8'1 | 109.5 |
H7A—C7—H7B | 108 | C7'—C8'—H8'2 | 109.5 |
C7—C8—C8A | 111.1 (4) | H8'1—C8'—H8'2 | 109.5 |
C7—C8—H8A | 109.4 | C7'—C8'—H8'3 | 109.5 |
C8A—C8—H8A | 109.4 | H8'1—C8'—H8'3 | 109.5 |
C7—C8—H8B | 109.4 | H8'2—C8'—H8'3 | 109.5 |
C8A—C8—H8B | 109.4 | C7'—C8'—H8'4 | 109.5 |
H8A—C8—H8B | 108 | H8'1—C8'—H8'4 | 141.1 |
C1—C8A—C4A | 114.5 (3) | H8'2—C8'—H8'4 | 56.3 |
C1—C8A—C8 | 111.8 (4) | H8'3—C8'—H8'4 | 56.3 |
C4A—C8A—C8 | 108.4 (3) | C7'—C8'—H8'5 | 109.5 |
C1—C8A—H8AA | 107.3 | H8'1—C8'—H8'5 | 56.3 |
C4A—C8A—H8AA | 107.3 | H8'2—C8'—H8'5 | 141.1 |
C8—C8A—H8AA | 107.3 | H8'3—C8'—H8'5 | 56.3 |
O3—C9—O4 | 123.7 (4) | H8'4—C8'—H8'5 | 109.5 |
O3—C9—C1 | 123.9 (5) | C7'—C8'—H8'6 | 109.5 |
O4—C9—C1 | 112.3 (4) | H8'1—C8'—H8'6 | 56.3 |
O4—C10—H10A | 109.5 | H8'2—C8'—H8'6 | 56.3 |
O4—C10—H10B | 109.5 | H8'3—C8'—H8'6 | 141.1 |
H10A—C10—H10B | 109.5 | H8'4—C8'—H8'6 | 109.5 |
O4—C10—H10C | 109.5 | H8'5—C8'—H8'6 | 109.5 |
H10A—C10—H10C | 109.5 | C7'—C9'—H9'1 | 109.5 |
H10B—C10—H10C | 109.5 | C7'—C9'—H9'2 | 109.5 |
O4—C10—H10D | 109.5 | H9'1—C9'—H9'2 | 109.5 |
H10A—C10—H10D | 141.1 | C7'—C9'—H9'3 | 109.5 |
H10B—C10—H10D | 56.3 | H9'1—C9'—H9'3 | 109.5 |
H10C—C10—H10D | 56.3 | H9'2—C9'—H9'3 | 109.5 |
O4—C10—H10E | 109.5 | C7'—C9'—H9'4 | 109.5 |
H10A—C10—H10E | 56.3 | H9'1—C9'—H9'4 | 141.1 |
H10B—C10—H10E | 141.1 | H9'2—C9'—H9'4 | 56.3 |
H10C—C10—H10E | 56.3 | H9'3—C9'—H9'4 | 56.3 |
H10D—C10—H10E | 109.5 | C7'—C9'—H9'5 | 109.5 |
O4—C10—H10F | 109.5 | H9'1—C9'—H9'5 | 56.3 |
H10A—C10—H10F | 56.3 | H9'2—C9'—H9'5 | 141.1 |
H10B—C10—H10F | 56.3 | H9'3—C9'—H9'5 | 56.3 |
H10C—C10—H10F | 141.1 | H9'4—C9'—H9'5 | 109.5 |
H10D—C10—H10F | 109.5 | C7'—C9'—H9'6 | 109.5 |
H10E—C10—H10F | 109.5 | H9'1—C9'—H9'6 | 56.3 |
O5—C11—O6 | 122.1 (4) | H9'2—C9'—H9'6 | 56.3 |
O5—C11—C2 | 124.7 (4) | H9'3—C9'—H9'6 | 141.1 |
O6—C11—C2 | 113.1 (4) | H9'4—C9'—H9'6 | 109.5 |
O6—C12—H12A | 109.5 | H9'5—C9'—H9'6 | 109.5 |
O6—C12—H12B | 109.5 | C1'—C10'—S | 112.1 (3) |
H12A—C12—H12B | 109.5 | C1'—C10'—H10G | 109.2 |
O6—C12—H12C | 109.5 | S—C10'—H10G | 109.2 |
H12A—C12—H12C | 109.5 | C1'—C10'—H10H | 109.2 |
H12B—C12—H12C | 109.5 | S—C10'—H10H | 109.2 |
C2'—C1'—C10' | 114.6 (3) | H10G—C10'—H10H | 107.9 |
C2'—C1'—C6' | 104.0 (3) | ||
C8A—C1—C2—C11 | −177.7 (4) | C3—C2—C11—O5 | 21.7 (7) |
C9—C1—C2—C11 | 0.4 (7) | C1—C2—C11—O6 | 26.2 (6) |
C8A—C1—C2—C3 | 3.6 (6) | C3—C2—C11—O6 | −154.9 (4) |
C9—C1—C2—C3 | −178.4 (4) | C10'—C1'—C2'—O2 | −34.8 (6) |
C1—C2—C3—C4 | −6.2 (6) | C6'—C1'—C2'—O2 | −162.9 (4) |
C11—C2—C3—C4 | 174.9 (3) | C7'—C1'—C2'—O2 | 91.1 (5) |
C2—C3—C4—C4A | 3.0 (6) | C10'—C1'—C2'—C3' | −159.8 (4) |
C2—C3—C4—S | 179.2 (3) | C6'—C1'—C2'—C3' | 72.1 (5) |
O1—S—C4—C4A | 138.0 (3) | C7'—C1'—C2'—C3' | −33.8 (5) |
C10'—S—C4—C4A | −111.4 (3) | O2—C2'—C3'—C4' | −121.9 (6) |
O1—S—C4—C3 | −38.5 (3) | C1'—C2'—C3'—C4' | −0.5 (6) |
C10'—S—C4—C3 | 72.1 (3) | C2'—C3'—C4'—C5' | −73.5 (5) |
C3—C4—C4A—C5 | 180.0 (4) | C2'—C3'—C4'—C7' | 35.4 (7) |
S—C4—C4A—C5 | 3.8 (6) | C3'—C4'—C5'—C6' | 71.8 (5) |
C3—C4—C4A—C8A | 2.9 (6) | C7'—C4'—C5'—C6' | −38.5 (7) |
S—C4—C4A—C8A | −173.3 (3) | C2'—C1'—C6'—C5' | −72.7 (5) |
C4—C4A—C5—C6 | −119.9 (4) | C10'—C1'—C6'—C5' | 160.3 (4) |
C8A—C4A—C5—C6 | 57.3 (5) | C7'—C1'—C6'—C5' | 35.5 (5) |
C4A—C5—C6—C7 | −54.7 (5) | C4'—C5'—C6'—C1' | 1.3 (6) |
C5—C6—C7—C8 | 55.4 (6) | C5'—C4'—C7'—C9' | −57.7 (8) |
C6—C7—C8—C8A | −57.2 (5) | C3'—C4'—C7'—C9' | −168.7 (7) |
C2—C1—C8A—C4A | 2.4 (5) | C5'—C4'—C7'—C8' | 174.3 (6) |
C9—C1—C8A—C4A | −175.8 (4) | C3'—C4'—C7'—C8' | 63.3 (8) |
C2—C1—C8A—C8 | −121.3 (4) | C5'—C4'—C7'—C1' | 58.3 (6) |
C9—C1—C8A—C8 | 60.5 (5) | C3'—C4'—C7'—C1' | −52.7 (6) |
C4—C4A—C8A—C1 | −5.6 (5) | C2'—C1'—C7'—C9' | 170.0 (5) |
C5—C4A—C8A—C1 | 176.9 (3) | C10'—C1'—C7'—C9' | −63.9 (6) |
C4—C4A—C8A—C8 | 119.9 (4) | C6'—C1'—C7'—C9' | 62.1 (5) |
C5—C4A—C8A—C8 | −57.6 (5) | C2'—C1'—C7'—C4' | 51.8 (6) |
C7—C8—C8A—C1 | −175.8 (4) | C10'—C1'—C7'—C4' | 177.9 (5) |
C7—C8—C8A—C4A | 57.1 (5) | C6'—C1'—C7'—C4' | −56.1 (6) |
C10—O4—C9—O3 | 6.6 (8) | C2'—C1'—C7'—C8' | −63.7 (6) |
C10—O4—C9—C1 | −177.0 (5) | C10'—C1'—C7'—C8' | 62.3 (7) |
C2—C1—C9—O3 | −119.1 (6) | C6'—C1'—C7'—C8' | −171.6 (6) |
C8A—C1—C9—O3 | 59.1 (6) | C2'—C1'—C10'—S | −53.0 (5) |
C2—C1—C9—O4 | 64.5 (5) | C6'—C1'—C10'—S | 68.6 (4) |
C8A—C1—C9—O4 | −117.3 (4) | C7'—C1'—C10'—S | −173.6 (4) |
C12—O6—C11—O5 | 8.6 (7) | O1—S—C10'—C1' | −74.2 (3) |
C12—O6—C11—C2 | −174.7 (4) | C4—S—C10'—C1' | 175.7 (3) |
C1—C2—C11—O5 | −157.2 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5B···S | 0.97 | 2.59 | 3.117 (4) | 114 |
O2—H2A···O1i | 0.82 | 1.88 | 2.683 (5) | 166 |
C10′—H10H···O5i | 0.97 | 2.59 | 3.534 (6) | 166 |
C3—H3B···O2ii | 0.97 | 2.36 | 3.191 (6) | 143 |
C10—H10D···O3 | 0.96 | 2.21 | 2.652 (9) | 107 |
C8′—H8′1···O2 | 0.96 | 2.37 | 3.01 (1) | 123 |
C8′—H8′6···O2 | 0.96 | 2.37 | 3.01 (1) | 123 |
Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z. |
Parameter | RX | AM1 | PM3 | PM5 | HFa | HFb | DFTc | DFTb |
S-O1 | 1.501 (3) | 1.4912 | 1.5566 | 1.4873 | 1.5014 | 1.4993 | 1.5249 | 1.5264 |
S-C4 | 1.804 (3) | 1.7221 | 1.8145 | 1.7590 | 1.7809 | 1.8030 | 1.8364 | 1.8319 |
S-C10' | 1.812 (3) | 1.7693 | 1.8575 | 1.8040 | 1.7993 | 1.8179 | 1.8646 | 1.8622 |
O2-C2' | 1.423 (5) | 1.4167 | 1.4114 | 1.3957 | 1.4518 | 1.4100 | 1.4385 | 1.4381 |
C1'-C10' | 1.520 (5) | 1.4943 | 1.5105 | 1.5022 | 1.5214 | 1.5275 | 1.5225 | 1.5231 |
S···O2 | 3.197 (5) | 3.4603 | 3.6651 | 3.4167 | 3.2662 | 3.4206 | 3.3863 | 3.4497 |
C9···O6 | 2.657 (6) | 3.1760 | 3.3648 | 2.8242 | 3.7293 | 3.4915 | 2.9644 | 3.0893 |
C11···O4 | 3.136 (5) | 2.8178 | 3.1848 | 2.7596 | 2.5298 | 2.5400 | 2.8309 | 2.7738 |
O1-S-C4 | 106.6 (2) | 105.72 | 105.13 | 106.63 | 105.84 | 105.50 | 106.23 | 105.90 |
O1-S-C10' | 107.1 (2) | 105.09 | 104.15 | 105.97 | 106.82 | 106.22 | 107.60 | 107.52 |
C4-S-C10' | 97.9 (2) | 99.56 | 97.29 | 97.00 | 98.07 | 98.27 | 97.24 | 96.58 |
O2-C2'-C1' | 110.2 (4) | 110.39 | 111.17 | 110.31 | 109.50 | 110.97 | 110.52 | 110.77 |
O1-S-C4-C4A | 138.0 (3) | 173.06 | 167.78 | 165.70 | 164.68 | 157.80 | 160.41 | 154.12 |
C2-C1-C9-O3 | -119.1 (6) | -138.81 | -111.45 | -132.68 | -78.74 | 174.03 | -131.77 | -123.21 |
C1-C2-C11-O5 | -157.2 (5) | -114.96 | -99.90 | -128.17 | 175.70 | -81.27 | -140.10 | -143.53 |
C2'-C1'-C10'-S | -53.0 (5) | -63.51 | -67.71 | -58.12 | -36.43 | -59.53 | -57.04 | -58.49 |
C4-S-C10'-C1' | 175.7 (3) | 168.49 | 164.42 | 177.55 | 173.93 | 175.06 | 175.67 | 179.58 |
Notes: (a) 3-21G*, (b) 6-31+G(d,p), (c) 6-31G(d) |