Stereochemical Characterization of Polyketide Stereotriads Synthesized via Hydrogen-Mediated Asymmetric syn-Crotylation.
Pantin, Mathilde; Hubert, Jonathan G.; Söhnel, Tilo; Brimble, Margaret A.; Furkert, Daniel P.; The Journal of organic chemistry 82 (2017) 11225–11229; doi:10.1021/acs.joc.7b01820

data_4032974
_publ_section_title
;
 Stereochemical Characterization of Polyketide Stereotriads Synthesized
 via Hydrogen-Mediated Asymmetric syn-Crotylation.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11225
_journal_page_last               11229
_journal_paper_doi               10.1021/acs.joc.7b01820
_journal_volume                  82
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H26 O2 Si'
_chemical_formula_sum            'C16 H26 O2 Si'
_chemical_formula_weight         278.46
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                85.237(7)
_cell_angle_beta                 84.232(7)
_cell_angle_gamma                76.806(7)
_cell_formula_units_Z            2
_cell_length_a                   6.9230(12)
_cell_length_b                   9.2252(16)
_cell_length_c                   13.527(2)
_cell_measurement_reflns_used    5027
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.267
_cell_measurement_theta_min      3.235
_cell_volume                     835.2(2)
_computing_cell_refinement       '<i>SAINT</i> (Bruker, 2008)'
_computing_data_collection       '<i>APEX2</i> (Bruker, 2008)'
_computing_data_reduction        '<i>SAINT</i> (Bruker, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.951
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'BRUKER APEXII'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_unetI/netI     0.0684
_diffrn_reflns_Laue_measured_fraction_full 0.951
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9012
_diffrn_reflns_point_group_measured_fraction_full 0.951
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.652
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4468
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1018 before and 0.0684 after correction.
The Ratio of minimum to maximum transmission is 0.5992.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.107
_exptl_crystal_description       fragment
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.545
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     356
_refine_ls_number_reflns         4513
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0472
_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^)+(0.0651P)^2^+0.2762P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1167
_refine_ls_wR_factor_ref         0.1254
_reflns_Friedel_coverage         1.000
_reflns_Friedel_fraction_full    0.951
_reflns_Friedel_fraction_max     0.951
_reflns_number_gt                3898
_reflns_number_total             4513
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b01820_si_002.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 4032973--4032974.cif.'
_cod_original_cell_volume        835.2(3)
_cod_database_code               4032974
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.947
_shelx_estimated_absorpt_t_max   0.986
_shelx_res_checksum              59708
_shelx_hkl_checksum              33672