Ozone Oxidation of Silylalkene: Mechanistic Study and Application for the Synthesis of Silacarboxylic Acid Derivatives.
Igawa, Kazunobu; Kawasaki, Yuuya; Nozaki, Sora; Kokan, Naoto; Tomooka, Katsuhiko; The Journal of organic chemistry 85 (2020) 4165–4171; doi:10.1021/acs.joc.9b03350

data_4038038
_publ_section_title
;
 Ozone Oxidation of Silylalkene: Mechanistic Study and Application for the
 Synthesis of Silacarboxylic Acid Derivatives.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4165
_journal_page_last               4171
_journal_paper_doi               10.1021/acs.joc.9b03350
_journal_volume                  85
_journal_year                    2020
_chemical_formula_moiety         'C20 H26 O2'
_chemical_formula_sum            'C20 H26 O2'
_chemical_formula_weight         298.41
_chemical_melting_point          349.2(5)
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-09-27
_audit_creation_method
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.043(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.8245(5)
_cell_length_b                   13.1695(12)
_cell_length_c                   26.813(3)
_cell_measurement_reflns_used    1515
_cell_measurement_temperature    123
_cell_measurement_theta_max      26.8600
_cell_measurement_theta_min      2.6880
_cell_volume                     1703.6(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.777
_diffrn_measurement_details
'List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames -------------------------------------------------------------------------- 1 \w 38.00 87.00 0.50 150.00 -- 5.00 45.00 150.00 98 2 \w 16.00 72.00 0.50 150.00 -- -10.00 45.00 30.00 112 3 \w -99.00 -12.00 0.50 150.00 -- -10.00 45.00 30.00 174'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC10 (RCD3): fixed-chi single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0144274000
_diffrn_orient_matrix_UB_12      -0.0336149000
_diffrn_orient_matrix_UB_13      0.0205401000
_diffrn_orient_matrix_UB_21      0.0016906000
_diffrn_orient_matrix_UB_22      -0.0420296000
_diffrn_orient_matrix_UB_23      -0.0165008000
_diffrn_orient_matrix_UB_31      0.1462827000
_diffrn_orient_matrix_UB_32      -0.0028543000
_diffrn_orient_matrix_UB_33      0.0022912000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0649
_diffrn_reflns_av_unetI/netI     0.0974
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.777
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            10403
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.777
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.913
_diffrn_reflns_theta_min         2.168
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86914
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.163
_exptl_crystal_description       needle
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         4170
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.1219
_refine_ls_R_factor_gt           0.0715
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0922P)^2^+0.0354P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1700
_refine_ls_wR_factor_ref         0.1930
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2573
_reflns_number_total             4170
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03350_si_001.cif
_cod_data_source_block           compound-s2
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '348.7-349.7 K' was changed
to '349.2(5)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 4038038.cif.
;
_cod_database_code               4038038
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C20H26O2
_reflns_odcompleteness_completeness 93.11
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.9586(10)
 0.0414(10)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
3. Others
 Sof(H18A)=Sof(C20A)=Sof(H20A)=Sof(C19A)=Sof(H19A)=Sof(C17A)=Sof(H17A)=
 Sof(C16A)=Sof(H16A)=1-FVAR(1)
 Sof(H18)=Sof(C16)=Sof(H16)=Sof(C17)=Sof(H17)=Sof(C19)=Sof(H19)=Sof(C20)=
 Sof(H20)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C10(H10A), C11(H11)
4.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C12(H12A,H12B), C9(H9A,H9B), C13(H13A,H13B), C7(H7A,H7B),
 C14(H14A,H14B)
4.c Aromatic/amide H refined with riding coordinates:
 C18(H18), C18(H18A), C2(H2), C6(H6), C16(H16), C3(H3), C4(H4), C17(H17),
 C5(H5), C19(H19), C20(H20), C20A(H20A), C19A(H19A), C17A(H17A), C16A(H16A)
4.d Idealised tetrahedral OH refined as rotating group:
 O10(H10), O9(H9)
;
_shelx_res_checksum              78398
_shelx_hkl_checksum              90391
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
'Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling'
_oxdiff_exptl_absorpt_empirical_full_max 1.325
_oxdiff_exptl_absorpt_empirical_full_min 0.778