A Study of Exocyclic Radical Reductions of Polysubstituted Tetrahydropyrans
François Godin; Michel Prévost; Frédérick Viens; Philippe Mochirian; Jean-François Brazeau; Serge I. Gorelsky; Yvan Guindon; Journal of Organic Chemistry 78 (2013) 6075–6103; doi:10.1021/jo400721e

data_4028341
_publ_section_title
;
 A Study of Exocyclic Radical Reductions of Polysubstituted
 Tetrahydropyrans
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6075
_journal_page_last               6103
_journal_paper_doi               10.1021/jo400721e
_journal_volume                  78
_journal_year                    2013
_chemical_compound_source        'Synthesized by the authors. See text'
_chemical_formula_moiety         'C12 H24 O3'
_chemical_formula_sum            'C12 H24 O3'
_chemical_formula_weight         216.31
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 90.833(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.3785(4)
_cell_length_b                   14.7508(5)
_cell_length_c                   18.4375(8)
_cell_measurement_reflns_used    4327
_cell_measurement_temperature    100
_cell_measurement_theta_max      70.21
_cell_measurement_theta_min      4.80
_cell_volume                     2550.38(18)
_computing_cell_refinement       'SAINT V7.68A(Bruker AXS, 2009)'
_computing_data_collection       'APEX2  (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A(Bruker AXS, 2009)'
_computing_molecular_graphics    'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_publication_material  'UdMX (Maris, 2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.936
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measurement_device_type  'Bruker APEX II'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  'Quazar MX'
_diffrn_radiation_source         'Incoatec I\muS Microsource '
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.048
_diffrn_reflns_av_sigmaI/netI    0.0275
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            21019
_diffrn_reflns_theta_full        70.65
_diffrn_reflns_theta_max         70.65
_diffrn_reflns_theta_min         4.80
_exptl_absorpt_coefficient_mu    0.629
_exptl_absorpt_correction_T_max  0.9875
_exptl_absorpt_correction_T_min  0.8690
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 2008)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.127
_exptl_crystal_description       NEEDLE
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Friedel Pairs merged'
_refine_ls_abs_structure_Flack   0.2(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         2301
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0507
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0867P)^2^+0.5021P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1283
_refine_ls_wR_factor_ref         0.1329
_reflns_number_gt                2035
_reflns_number_total             2301
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo400721e_si_002.cif
_cod_data_source_block           guin73
_cod_database_code               4028341