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_4128615
_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            'C16 H22 O3'
_chemical_formula_weight         262.33
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     'dual space'
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                87.3040(9)
_cell_angle_beta                 75.4289(9)
_cell_angle_gamma                76.0963(9)
_cell_formula_units_Z            6
_cell_length_a                   12.1239(8)
_cell_length_b                   13.1282(9)
_cell_length_c                   14.4151(10)
_cell_measurement_reflns_used    8597
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      28.17
_cell_measurement_theta_min      2.18
_cell_volume                     2155.3(3)
_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 0.996
_diffrn_measured_fraction_theta_max 0.947
_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  0.0273
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            25547
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         28.299
_diffrn_reflns_theta_min         1.598
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.8621
_exptl_absorpt_correction_T_min  0.8090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS 2014/5'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    not_measured
_exptl_crystal_description       prism
_exptl_crystal_F_000             852
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.276
_exptl_crystal_size_min          0.230
_refine_diff_density_max         1.192
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     564
_refine_ls_number_reflns         10157
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0882
_refine_ls_R_factor_gt           0.0622
_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^)+(0.0841P)^2^+1.5504P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1582
_refine_ls_wR_factor_ref         0.1758
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7437
_reflns_number_total             10157
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b07346_si_002.cif
_cod_data_source_block           svp13
_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_database_code               4128615
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.967
_shelx_estimated_absorpt_t_max   0.981
_exptl_absorpt_special_details
; 
Reflections not merged 
25586 Corrected reflections written to file svp13s.hkl 
Estimated minimum and maximum transmission:  0.8090  0.8621 
The ratio (0.9384) 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              69599
_shelx_hkl_checksum              63064