Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805008032/is6060sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805008032/is6060Isup2.hkl |
CCDC reference: 270461
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.004 Å
- R factor = 0.056
- wR factor = 0.126
- Data-to-parameter ratio = 16.2
checkCIF/PLATON results
No syntax errors found
Alert level A PLAT052_ALERT_1_A (Proper) Absorption Correction Method Missing .. ? PLAT057_ALERT_3_A Correction for Absorption Required RT(exp) ... 1.43
Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 44 Perc. PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.96 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.34 PLAT417_ALERT_2_C Short Inter D-H..H-D H2S .. H2S .. 2.13 Ang. PLAT420_ALERT_2_C D-H Without Acceptor S1 - H1S ... ? PLAT420_ALERT_2_C D-H Without Acceptor S2 - H2S ... ?
2 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1992); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: CrystalStructure (Molecular Structure Corporation & Rigaku, 2001); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Watkin et al., 1996); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.
C23H48S2 | Z = 2 |
Mr = 388.75 | F(000) = 436.00 |
Triclinic, P1 | Dx = 1.043 Mg m−3 |
Hall symbol: -P 1 | Cu Kα radiation, λ = 1.5418 Å |
a = 4.7477 (5) Å | Cell parameters from 23 reflections |
b = 5.5644 (8) Å | θ = 9.8–18.0° |
c = 47.983 (3) Å | µ = 1.94 mm−1 |
α = 90.205 (9)° | T = 296 K |
β = 90.523 (7)° | Plate, colourless |
γ = 102.288 (10)° | 0.58 × 0.20 × 0.03 mm |
V = 1238.5 (2) Å3 |
Rigaku AFC-5R diffractometer | Rint = 0.033 |
ω scans | θmax = 70.1° |
Absorption correction: ψ scan (North et al., 1968) | h = −5→5 |
Tmin = 0.710, Tmax = 0.945 | k = −1→6 |
6047 measured reflections | l = −58→58 |
4513 independent reflections | 3 standard reflections every 150 reflections |
1976 reflections with F2 > 2σ(F2) | intensity decay: 18.1% |
Refinement on F2 | w = (4Fo2)/[0.0001Fo2 + 2.7σ2(Fo) + 0.27] |
R[F2 > 2σ(F2)] = 0.056 | (Δ/σ)max < 0.001 |
wR(F2) = 0.126 | Δρmax = 0.60 e Å−3 |
S = 1.00 | Δρmin = −0.64 e Å−3 |
4513 reflections | Extinction correction: Larson (1970) |
279 parameters | Extinction coefficient: 13.4 (1) |
H atoms treated by a mixture of independent and constrained refinement |
Experimental. The molecule of (I) is non-centrosymmetric, so a longer data collection time was needed. Therefore, the intensity decay of (I) became somewhat high. |
Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY |
Refinement. Refinement using reflections with F2 > -10.0 σ(F2). The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt). |
x | y | z | Uiso*/Ueq | ||
S1 | 0.8665 (3) | 2.2653 (2) | 0.97538 (2) | 0.0949 (5) | |
S2 | −0.1627 (3) | −1.8040 (2) | 0.52158 (2) | 0.0969 (5) | |
C1 | 0.6219 (8) | 2.0204 (6) | 0.95791 (7) | 0.075 (1) | |
C2 | 0.7568 (7) | 1.8882 (6) | 0.93605 (6) | 0.057 (1) | |
C3 | 0.5399 (7) | 1.6924 (6) | 0.92061 (6) | 0.057 (1) | |
C4 | 0.6731 (7) | 1.5532 (6) | 0.89895 (6) | 0.053 (1) | |
C5 | 0.4562 (7) | 1.3622 (6) | 0.88308 (6) | 0.053 (1) | |
C6 | 0.5863 (7) | 1.2215 (6) | 0.86135 (6) | 0.051 (1) | |
C7 | 0.3679 (7) | 1.0307 (5) | 0.84544 (6) | 0.051 (1) | |
C8 | 0.4983 (7) | 0.8887 (6) | 0.82382 (6) | 0.050 (1) | |
C9 | 0.2799 (7) | 0.6984 (5) | 0.80784 (6) | 0.051 (1) | |
C10 | 0.4100 (7) | 0.5564 (5) | 0.78627 (6) | 0.050 (1) | |
C11 | 0.1922 (7) | 0.3678 (5) | 0.77024 (6) | 0.050 (1) | |
C12 | 0.3223 (7) | 0.2239 (6) | 0.74877 (6) | 0.050 (1) | |
C13 | 0.1032 (7) | 0.0346 (6) | 0.73270 (6) | 0.050 (1) | |
C14 | 0.2346 (7) | −0.1081 (6) | 0.71122 (6) | 0.050 (1) | |
C15 | 0.0161 (7) | −0.2965 (5) | 0.69509 (6) | 0.050 (1) | |
C16 | 0.1460 (7) | −0.4406 (5) | 0.67366 (6) | 0.051 (1) | |
C17 | −0.0721 (7) | −0.6287 (5) | 0.65739 (6) | 0.051 (1) | |
C18 | 0.0598 (7) | −0.7728 (6) | 0.63611 (6) | 0.052 (1) | |
C19 | −0.1581 (7) | −0.9599 (6) | 0.61967 (6) | 0.054 (1) | |
C20 | −0.0257 (7) | −1.1038 (6) | 0.59840 (6) | 0.054 (1) | |
C21 | −0.2424 (7) | −1.2869 (6) | 0.58163 (6) | 0.058 (1) | |
C22 | −0.1056 (7) | −1.4357 (6) | 0.56119 (6) | 0.060 (1) | |
C23 | −0.3233 (8) | −1.6094 (6) | 0.54365 (7) | 0.076 (1) | |
H1 | 0.5385 | 1.9038 | 0.97152 | 0.089* | |
H2 | 0.4750 | 2.0869 | 0.94922 | 0.089* | |
H3 | 0.8501 | 2.0054 | 0.92294 | 0.068* | |
H4 | 0.8952 | 1.8121 | 0.94482 | 0.068* | |
H5 | 0.4435 | 1.5778 | 0.93383 | 0.068* | |
H6 | 0.4043 | 1.7695 | 0.91153 | 0.068* | |
H7 | 0.7734 | 1.6683 | 0.88598 | 0.063* | |
H8 | 0.8054 | 1.4729 | 0.90809 | 0.063* | |
H9 | 0.3559 | 1.2476 | 0.89609 | 0.064* | |
H10 | 0.3241 | 1.4429 | 0.87397 | 0.064* | |
H11 | 0.6871 | 1.3361 | 0.84836 | 0.062* | |
H12 | 0.7179 | 1.1402 | 0.87046 | 0.062* | |
H13 | 0.2663 | 0.9167 | 0.85844 | 0.061* | |
H14 | 0.2370 | 1.1121 | 0.83624 | 0.061* | |
H15 | 0.6004 | 1.0028 | 0.81085 | 0.060* | |
H16 | 0.6288 | 0.8070 | 0.83303 | 0.060* | |
H17 | 0.1777 | 0.5845 | 0.82082 | 0.061* | |
H18 | 0.1496 | 0.7802 | 0.79861 | 0.061* | |
H19 | 0.5132 | 0.6704 | 0.77335 | 0.060* | |
H20 | 0.5395 | 0.4739 | 0.79551 | 0.060* | |
H21 | 0.0881 | 0.2546 | 0.78318 | 0.060* | |
H22 | 0.0636 | 0.4506 | 0.76089 | 0.060* | |
H23 | 0.4265 | 0.3371 | 0.73583 | 0.060* | |
H24 | 0.4508 | 0.1410 | 0.75812 | 0.060* | |
H25 | −0.0008 | −0.0789 | 0.74561 | 0.060* | |
H26 | −0.0256 | 0.1173 | 0.72337 | 0.061* | |
H27 | 0.3391 | 0.0055 | 0.69834 | 0.060* | |
H28 | 0.3629 | −0.1912 | 0.72056 | 0.060* | |
H29 | −0.0889 | −0.4095 | 0.70800 | 0.061* | |
H30 | −0.1118 | −0.2131 | 0.68571 | 0.061* | |
H31 | 0.2516 | −0.3274 | 0.66081 | 0.061* | |
H32 | 0.2733 | −0.5243 | 0.68307 | 0.061* | |
H33 | −0.1783 | −0.7417 | 0.67022 | 0.061* | |
H34 | −0.1989 | −0.5451 | 0.64789 | 0.061* | |
H35 | 0.1672 | −0.6597 | 0.62336 | 0.063* | |
H36 | 0.1857 | −0.8573 | 0.64563 | 0.063* | |
H37 | −0.2655 | −1.0731 | 0.63241 | 0.065* | |
H38 | −0.2840 | −0.8755 | 0.61015 | 0.066* | |
H39 | 0.0847 | −0.9902 | 0.58588 | 0.065* | |
H40 | 0.0974 | −1.1906 | 0.60797 | 0.066* | |
H41 | −0.3577 | −1.3971 | 0.59414 | 0.069* | |
H42 | −0.3610 | −1.1999 | 0.57145 | 0.070* | |
H43 | 0.0168 | −1.3253 | 0.54920 | 0.072* | |
H44 | 0.0057 | −1.5290 | 0.57141 | 0.072* | |
H45 | −0.4230 | −1.5153 | 0.53221 | 0.091* | |
H46 | −0.4561 | −1.7102 | 0.55566 | 0.091* | |
H1S | 0.941 (8) | 2.201 (6) | 0.9907 (7) | 0.1139* | |
H2S | −0.131 (8) | −1.677 (6) | 0.5041 (7) | 0.1160* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.118 (1) | 0.0823 (9) | 0.0778 (8) | 0.0071 (8) | −0.0179 (8) | −0.0401 (7) |
S2 | 0.127 (1) | 0.0849 (9) | 0.0808 (8) | 0.0273 (8) | 0.0002 (8) | −0.0422 (7) |
C1 | 0.080 (3) | 0.076 (3) | 0.067 (2) | 0.012 (2) | 0.004 (2) | −0.033 (2) |
C2 | 0.066 (3) | 0.052 (2) | 0.051 (2) | 0.013 (2) | −0.002 (2) | −0.013 (2) |
C3 | 0.056 (3) | 0.057 (2) | 0.057 (2) | 0.010 (2) | −0.001 (2) | −0.023 (2) |
C4 | 0.052 (2) | 0.051 (2) | 0.054 (2) | 0.007 (2) | −0.003 (2) | −0.020 (2) |
C5 | 0.050 (2) | 0.057 (2) | 0.052 (2) | 0.010 (2) | 0.001 (2) | −0.020 (2) |
C6 | 0.053 (3) | 0.052 (2) | 0.049 (2) | 0.011 (2) | −0.001 (2) | −0.018 (2) |
C7 | 0.051 (2) | 0.050 (2) | 0.050 (2) | 0.007 (2) | −0.001 (2) | −0.019 (2) |
C8 | 0.050 (2) | 0.050 (2) | 0.050 (2) | 0.008 (2) | −0.003 (2) | −0.018 (2) |
C9 | 0.052 (2) | 0.052 (2) | 0.048 (2) | 0.010 (2) | −0.003 (2) | −0.019 (2) |
C10 | 0.052 (2) | 0.049 (2) | 0.048 (2) | 0.010 (2) | −0.003 (2) | −0.016 (2) |
C11 | 0.050 (2) | 0.050 (2) | 0.049 (2) | 0.010 (2) | −0.002 (2) | −0.019 (2) |
C12 | 0.051 (2) | 0.050 (2) | 0.048 (2) | 0.009 (2) | −0.003 (2) | −0.019 (2) |
C13 | 0.052 (2) | 0.053 (2) | 0.046 (2) | 0.011 (2) | −0.000 (2) | −0.018 (2) |
C14 | 0.048 (2) | 0.053 (2) | 0.048 (2) | 0.009 (2) | −0.001 (2) | −0.020 (2) |
C15 | 0.050 (2) | 0.052 (2) | 0.049 (2) | 0.011 (2) | −0.002 (2) | −0.017 (2) |
C16 | 0.053 (2) | 0.049 (2) | 0.050 (2) | 0.011 (2) | −0.001 (2) | −0.017 (2) |
C17 | 0.053 (2) | 0.050 (2) | 0.048 (2) | 0.009 (2) | −0.001 (2) | −0.017 (2) |
C18 | 0.055 (3) | 0.054 (2) | 0.047 (2) | 0.013 (2) | −0.001 (2) | −0.018 (2) |
C19 | 0.059 (3) | 0.055 (2) | 0.050 (2) | 0.013 (2) | −0.002 (2) | −0.018 (2) |
C20 | 0.055 (3) | 0.057 (2) | 0.051 (2) | 0.013 (2) | 0.000 (2) | −0.021 (2) |
C21 | 0.055 (3) | 0.063 (2) | 0.056 (2) | 0.011 (2) | −0.002 (2) | −0.024 (2) |
C22 | 0.063 (3) | 0.063 (2) | 0.054 (2) | 0.013 (2) | −0.007 (2) | −0.025 (2) |
C23 | 0.074 (3) | 0.079 (3) | 0.074 (3) | 0.013 (2) | −0.007 (2) | −0.035 (2) |
S1—C1 | 1.791 (3) | C6—H11 | 0.95 |
S2—C23 | 1.798 (3) | C6—H12 | 0.95 |
C1—C2 | 1.503 (4) | C7—H13 | 0.95 |
C2—C3 | 1.516 (4) | C7—H14 | 0.95 |
C3—C4 | 1.515 (3) | C8—H15 | 0.95 |
C4—C5 | 1.511 (3) | C8—H16 | 0.95 |
C5—C6 | 1.515 (3) | C9—H17 | 0.95 |
C6—C7 | 1.515 (3) | C9—H18 | 0.95 |
C7—C8 | 1.516 (3) | C10—H19 | 0.95 |
C8—C9 | 1.516 (3) | C10—H20 | 0.95 |
C9—C10 | 1.513 (3) | C11—H21 | 0.95 |
C10—C11 | 1.510 (3) | C11—H22 | 0.95 |
C11—C12 | 1.516 (3) | C12—H23 | 0.95 |
C12—C13 | 1.516 (3) | C12—H24 | 0.95 |
C13—C14 | 1.516 (3) | C13—H25 | 0.95 |
C14—C15 | 1.513 (3) | C13—H26 | 0.95 |
C15—C16 | 1.515 (3) | C14—H27 | 0.95 |
C16—C17 | 1.515 (3) | C14—H28 | 0.95 |
C17—C18 | 1.516 (3) | C15—H29 | 0.95 |
C18—C19 | 1.516 (3) | C15—H30 | 0.95 |
C19—C20 | 1.516 (3) | C16—H31 | 0.95 |
C20—C21 | 1.509 (3) | C16—H32 | 0.95 |
C21—C22 | 1.518 (4) | C17—H33 | 0.95 |
C22—C23 | 1.505 (4) | C17—H34 | 0.95 |
S1—H1S | 0.92 (3) | C18—H35 | 0.95 |
S2—H2S | 1.09 (3) | C18—H36 | 0.95 |
C1—H1 | 0.95 | C19—H37 | 0.95 |
C1—H2 | 0.95 | C19—H38 | 0.95 |
C2—H3 | 0.95 | C20—H39 | 0.95 |
C2—H4 | 0.95 | C20—H40 | 0.95 |
C3—H5 | 0.95 | C21—H41 | 0.95 |
C3—H6 | 0.95 | C21—H42 | 0.95 |
C4—H7 | 0.95 | C22—H43 | 0.95 |
C4—H8 | 0.95 | C22—H44 | 0.95 |
C5—H9 | 0.95 | C23—H45 | 0.95 |
C5—H10 | 0.95 | C23—H46 | 0.95 |
S1i···S1ii | 3.5360 (16) | S2···S2iii | 3.5908 (16) |
C1—S1—H1S | 108 (2) | C11—C10—H19 | 108.2 |
C23—S2—H2S | 94.8 (18) | C9—C10—H20 | 108.3 |
S1—C1—C2 | 114.8 (3) | C11—C10—H20 | 108.3 |
C1—C2—C3 | 113.1 (3) | H19—C10—H20 | 109.5 |
C2—C3—C4 | 113.8 (3) | C10—C11—H21 | 108.2 |
C3—C4—C5 | 113.8 (3) | C12—C11—H21 | 108.2 |
C4—C5—C6 | 114.4 (3) | C10—C11—H22 | 108.2 |
C5—C6—C7 | 114.2 (3) | C12—C11—H22 | 108.2 |
C6—C7—C8 | 114.2 (3) | H21—C11—H22 | 109.5 |
C7—C8—C9 | 114.3 (3) | C11—C12—H23 | 108.3 |
C8—C9—C10 | 114.3 (3) | C13—C12—H23 | 108.3 |
C9—C10—C11 | 114.3 (3) | C11—C12—H24 | 108.2 |
C10—C11—C12 | 114.4 (3) | C13—C12—H24 | 108.2 |
C11—C12—C13 | 114.3 (3) | H23—C12—H24 | 109.5 |
C12—C13—C14 | 114.0 (3) | C12—C13—H25 | 108.4 |
C13—C14—C15 | 114.1 (3) | C14—C13—H25 | 108.3 |
C14—C15—C16 | 114.3 (3) | C12—C13—H26 | 108.3 |
C15—C16—C17 | 114.5 (3) | C14—C13—H26 | 108.3 |
C16—C17—C18 | 114.2 (3) | H25—C13—H26 | 109.5 |
C17—C18—C19 | 114.2 (3) | C13—C14—H27 | 108.3 |
C18—C19—C20 | 114.1 (3) | C15—C14—H27 | 108.3 |
C19—C20—C21 | 114.3 (3) | C13—C14—H28 | 108.3 |
C20—C21—C22 | 113.5 (3) | C15—C14—H28 | 108.3 |
C21—C22—C23 | 113.1 (3) | H27—C14—H28 | 109.5 |
S2—C23—C22 | 113.0 (2) | C14—C15—H29 | 108.2 |
S1—C1—H1 | 108.0 | C16—C15—H29 | 108.3 |
C2—C1—H1 | 108.1 | C14—C15—H30 | 108.2 |
S1—C1—H2 | 108.3 | C16—C15—H30 | 108.2 |
C2—C1—H2 | 108.2 | H29—C15—H30 | 109.5 |
H1—C1—H2 | 109.5 | C15—C16—H31 | 108.2 |
C1—C2—H3 | 108.5 | C17—C16—H31 | 108.2 |
C3—C2—H3 | 108.6 | C15—C16—H32 | 108.2 |
C1—C2—H4 | 108.6 | C17—C16—H32 | 108.2 |
C3—C2—H4 | 108.5 | H31—C16—H32 | 109.5 |
H3—C2—H4 | 109.5 | C16—C17—H33 | 108.3 |
C2—C3—H5 | 108.4 | C18—C17—H33 | 108.3 |
C4—C3—H5 | 108.4 | C16—C17—H34 | 108.3 |
C2—C3—H6 | 108.4 | C18—C17—H34 | 108.3 |
C4—C3—H6 | 108.4 | H33—C17—H34 | 109.5 |
H5—C3—H6 | 109.5 | C17—C18—H35 | 108.3 |
C3—C4—H7 | 108.4 | C19—C18—H35 | 108.3 |
C5—C4—H7 | 108.4 | C17—C18—H36 | 108.3 |
C3—C4—H8 | 108.4 | C19—C18—H36 | 108.3 |
C5—C4—H8 | 108.4 | H35—C18—H36 | 109.5 |
H7—C4—H8 | 109.5 | C18—C19—H37 | 108.3 |
C4—C5—H9 | 108.2 | C20—C19—H37 | 108.3 |
C6—C5—H9 | 108.2 | C18—C19—H38 | 108.3 |
C4—C5—H10 | 108.2 | C20—C19—H38 | 108.3 |
C6—C5—H10 | 108.2 | H37—C19—H38 | 109.5 |
H9—C5—H10 | 109.5 | C19—C20—H39 | 108.2 |
C5—C6—H11 | 108.3 | C21—C20—H39 | 108.3 |
C7—C6—H11 | 108.3 | C19—C20—H40 | 108.3 |
C5—C6—H12 | 108.3 | C21—C20—H40 | 108.3 |
C7—C6—H12 | 108.3 | H39—C20—H40 | 109.4 |
H11—C6—H12 | 109.5 | C20—C21—H41 | 108.5 |
C6—C7—H13 | 108.3 | C22—C21—H41 | 108.5 |
C8—C7—H13 | 108.3 | C20—C21—H42 | 108.5 |
C6—C7—H14 | 108.2 | C22—C21—H42 | 108.4 |
C8—C7—H14 | 108.3 | H41—C21—H42 | 109.5 |
H13—C7—H14 | 109.5 | C21—C22—H43 | 108.6 |
C7—C8—H15 | 108.3 | C23—C22—H43 | 108.6 |
C9—C8—H15 | 108.3 | C21—C22—H44 | 108.5 |
C7—C8—H16 | 108.3 | C23—C22—H44 | 108.5 |
C9—C8—H16 | 108.3 | H43—C22—H44 | 109.5 |
H15—C8—H16 | 109.5 | S2—C23—H45 | 108.5 |
C8—C9—H17 | 108.2 | C22—C23—H45 | 108.5 |
C10—C9—H17 | 108.3 | S2—C23—H46 | 108.7 |
C8—C9—H18 | 108.3 | C22—C23—H46 | 108.6 |
C10—C9—H18 | 108.2 | H45—C23—H46 | 109.5 |
H17—C9—H18 | 109.5 | S1i—H1Si—S1ii | 95 (2) |
C9—C10—H19 | 108.3 | S2—H2S—S2iii | 76.9 (18) |
S1—C1—C2—C3 | −176.7 (2) | C12—C13—C14—C15 | −179.8 (3) |
C1—C2—C3—C4 | −178.7 (3) | C13—C14—C15—C16 | −179.7 (3) |
C2—C3—C4—C5 | −178.6 (3) | C14—C15—C16—C17 | −179.8 (3) |
C3—C4—C5—C6 | −180.0 (3) | C15—C16—C17—C18 | −179.7 (3) |
C4—C5—C6—C7 | −179.9 (3) | C16—C17—C18—C19 | −179.6 (3) |
C5—C6—C7—C8 | −179.6 (3) | C17—C18—C19—C20 | 180.0 (3) |
C6—C7—C8—C9 | −179.8 (3) | C18—C19—C20—C21 | −178.9 (3) |
C7—C8—C9—C10 | −179.9 (3) | C19—C20—C21—C22 | −177.9 (3) |
C8—C9—C10—C11 | −179.7 (3) | C20—C21—C22—C23 | −177.4 (3) |
C9—C10—C11—C12 | −179.6 (3) | C21—C22—C23—S2 | −175.0 (2) |
C10—C11—C12—C13 | 180.0 (3) | C2—C1—S1—H1S | −90 (2) |
C11—C12—C13—C14 | 179.8 (3) | C22—C23—S2—H2S | −90 (2) |
Symmetry codes: (i) x−1, y−1, z−1; (ii) −x+1, −y+4, −z+1; (iii) −x, −y−4, −z+1. |