A Radical-Polar Crossover Annulation To Access Terpenoid Motifs.
Thomas, William P.; Schatz, Devon J.; George, David T.; Pronin, Sergey V.; Journal of the American Chemical Society 141 (2019) 12246–12250; doi:10.1021/jacs.9b07346

data_4128616
_publ_section_title
;
 A Radical-Polar Crossover Annulation To Access Terpenoid Motifs.
;
_journal_issue                   31
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12246
_journal_page_last               12250
_journal_paper_doi               10.1021/jacs.9b07346
_journal_volume                  141
_journal_year                    2019
_chemical_formula_sum            'C21 H32 O6'
_chemical_formula_weight         380.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 106.0167(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.3869(6)
_cell_length_b                   11.0755(6)
_cell_length_c                   16.4649(9)
_cell_measurement_reflns_used    9974
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      28.67
_cell_measurement_theta_min      2.57
_cell_volume                     1995.87(19)
_computing_cell_refinement       'Bruker SAINT 8.34a, 2013'
_computing_data_collection       'Bruker APEX2 2014.11-0, 2014'
_computing_data_reduction        'Bruker SAINT 8.34a, 2013'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL 2014/4'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            23515
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         28.854
_diffrn_reflns_theta_min         1.861
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.8621
_exptl_absorpt_correction_T_min  0.8233
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS 2014/5'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    not_measured
_exptl_crystal_description       irregular
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.417
_exptl_crystal_size_mid          0.356
_exptl_crystal_size_min          0.193
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     372
_refine_ls_number_reflns         4932
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0362
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0534P)^2^+0.6176P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0946
_refine_ls_wR_factor_ref         0.1004
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4236
_reflns_number_total             4932
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b07346_si_004.cif
_cod_data_source_block           svp15
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not_measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4128616
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.963
_shelx_estimated_absorpt_t_max   0.983
_exptl_absorpt_special_details
; 
Reflections not merged 
24212 Corrected reflections written to file svp15s.hkl 
Estimated minimum and maximum transmission:  0.8233  0.8621 
The ratio (0.9550) of these values is more reliable than their absolute values 
Additional spherical absorption correction applied with mu*r =  0.1000 
Lambda/2 correction factor = 0.00150 
;
_shelx_res_checksum              94112
_shelx_hkl_checksum              45734