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The title compound, C24H34O6S, (I), is an enantiopure sulfinyl adduct, prepared via stereocontrolled Diels-Alder cycloaddition. The solid-state structure of (I) has been determined at room temperature by single-crystal X-ray diffraction. It is chemically similar to other cited structures; however, it presents a peculiar packing arrangement. Ab initio, density-functional theory (DFT) and semi-empirical (AM1, PM3 and PM5) full-geometry optimizations were carried out for (I). Calculated values of the structural parameters have been compared with those obtained by X-ray crystallography.
Supporting information
CCDC reference: 239129
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.007 Å
- R factor = 0.042
- wR factor = 0.101
- Data-to-parameter ratio = 9.4
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.44 Ratio
PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.05 Ratio
PLAT241_ALERT_2_B Check High U(eq) as Compared to Neighbors .... C3'
PLAT242_ALERT_2_B Check Low U(eq) as Compared to Neighbors .... C7'
PLAT413_ALERT_2_B Short Inter XH3 .. XHn H4'A .. H10E .. 2.09 Ang.
Alert level C
PLAT213_ALERT_2_C Atom C4' has ADP max/min Ratio ............. 3.10 prolat
PLAT213_ALERT_2_C Atom C8' has ADP max/min Ratio ............. 3.10 prolat
PLAT213_ALERT_2_C Atom C9' has ADP max/min Ratio ............. 3.10 prolat
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C1'
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C2'
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C9
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C11
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.08
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
PLAT413_ALERT_2_C Short Inter XH3 .. XHn H4'A .. H10A .. 2.14 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 21
Alert level G
REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may
be needed to determine absolute structure
From the CIF: _diffrn_reflns_theta_max 25.00
From the CIF: _reflns_number_total 2642
Count of symmetry unique reflns 2076
Completeness (_total/calc) 127.26%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 566
Fraction of Friedel pairs measured 0.273
Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem
5 ALERT level B = Potentially serious problem
11 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
13 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
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).
(8aR,S
S)-Dimethyl
3,5,6,7,8,8a-hexahydro-4-{[(1
S)-
exo-2-hydroxy-7,7-
dimethylbicyclo[2.2.1]heptan-1-yl]methylsulfinyl}-1,2-naphthalenedicarboxylate
top
Crystal data top
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 | |
Data collection top
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 top
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 | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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* | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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) | | |
Hydrogen-bond geometry (Å, º) top
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. |
Selected bond lenghts (Å), angles and torsion angles (°)
for (I). X-ray diffraction determination (RX) is compared to
several computations (AM1, PM3, PM5, HF and DFT). topParameter | 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) |
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