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_4028342
_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         'C24 H30 Br N O4'
_chemical_formula_sum            'C24 H30 Br N O4'
_chemical_formula_weight         476.40
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 99.713(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.8892(14)
_cell_length_b                   5.0802(3)
_cell_length_c                   24.1881(18)
_cell_measurement_reflns_used    3957
_cell_measurement_temperature    150
_cell_measurement_theta_max      54.73
_cell_measurement_theta_min      2.37
_cell_volume                     2287.8(3)
_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    'SIR2004 (Burla et al., 2004)'
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 5.5
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Smart 6000'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  'Helios optics'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.159
_diffrn_reflns_av_sigmaI/netI    0.0996
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            56981
_diffrn_reflns_theta_full        65.12
_diffrn_reflns_theta_max         65.12
_diffrn_reflns_theta_min         2.37
_exptl_absorpt_coefficient_mu    2.687
_exptl_absorpt_correction_T_max  0.8066
_exptl_absorpt_correction_T_min  0.5592
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 2008)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_description       needle
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.336
_refine_diff_density_min         -0.878
_refine_diff_density_rms         0.137
_refine_ls_extinction_coef       0.0017(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3878
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.1471
_refine_ls_R_factor_gt           0.0888
_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^)+(0.1409P)^2^+2.9252P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2211
_refine_ls_wR_factor_ref         0.2509
_reflns_number_gt                2293
_reflns_number_total             3878
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo400721e_si_003.cif
_cod_data_source_block           guin67
_cod_database_code               4028342