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_4032973
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.3872(5)
_cell_length_b                   13.6568(9)
_cell_length_c                   18.5349(12)
_cell_measurement_reflns_used    2866
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.245
_cell_measurement_theta_min      3.331
_cell_volume                     1616.8(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 0.866
_diffrn_measured_fraction_theta_max 0.960
_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  0.0947
_diffrn_reflns_av_unetI/netI     0.1107
_diffrn_reflns_Laue_measured_fraction_full 0.866
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9460
_diffrn_reflns_point_group_measured_fraction_full 0.862
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.249
_diffrn_reflns_theta_min         1.852
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_T_max  0.7450
_exptl_absorpt_correction_T_min  0.6112
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1191 before and 0.0740 after correction.
The Ratio of minimum to maximum transmission is 0.8204.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.144
_exptl_crystal_description       needle
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         2495
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.982
_refine_ls_R_factor_all          0.0821
_refine_ls_R_factor_gt           0.0462
_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^)+(0.0312P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0819
_refine_ls_wR_factor_ref         0.0916
_reflns_Friedel_coverage         0.701
_reflns_Friedel_fraction_full    0.855
_reflns_Friedel_fraction_max     0.958
_reflns_number_gt                1823
_reflns_number_total             2495
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b01820_si_003.cif
_cod_data_source_block           map_sos
_cod_depositor_comments
'Adding full bibliography for 4032973--4032974.cif.'
_cod_database_code               4032973
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.959
_shelx_estimated_absorpt_t_max   0.986
_shelxl_version_number           2013-2
_shelx_res_checksum              74633
_shelx_hkl_checksum              35927