Catalytic Asymmetric Radical-Polar Crossover Hydroalkoxylation.
Discolo, Christopher A.; Touney, Eric E.; Pronin, Sergey V.; Journal of the American Chemical Society  (2019) –; doi:10.1021/jacs.9b10645

data_4127300
_publ_section_title
;
 Catalytic Asymmetric Radical-Polar Crossover Hydroalkoxylation.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.9b10645
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_sum            'C14 H19 N O3 S'
_chemical_formula_weight         281.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     'dual space'
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 101.6262(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.3614(8)
_cell_length_b                   8.2138(6)
_cell_length_c                   16.4833(12)
_cell_measurement_reflns_used    7811
_cell_measurement_temperature    88(2)
_cell_measurement_theta_max      28.97
_cell_measurement_theta_min      2.52
_cell_volume                     1374.05(18)
_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      88(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.922
_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  0.0386
_diffrn_reflns_av_unetI/netI     0.0630
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.922
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14833
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.866
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         29.174
_diffrn_reflns_theta_min         1.261
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.239
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6895
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS 2014/5'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    not_measured
_exptl_crystal_description       irregular
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.258
_exptl_crystal_size_mid          0.171
_exptl_crystal_size_min          0.139
_refine_diff_density_max         0.775
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details
; 
 Flack x determined using 1963 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.04(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         6440
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0517
_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^)+(0.0428P)^2^+0.8592P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1109
_refine_ls_wR_factor_ref         0.1191
_reflns_Friedel_coverage         0.762
_reflns_Friedel_fraction_full    0.950
_reflns_Friedel_fraction_max     0.803
_reflns_number_gt                5448
_reflns_number_total             6440
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b10645_si_002.cif
_cod_data_source_block           svp18
_cod_depositor_comments
;
The following automatic conversions were performed:

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

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               4127300
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.941
_shelx_estimated_absorpt_t_max   0.967
_exptl_absorpt_special_details
; 
Reflections not merged 
14848 Corrected reflections written to file svp18s.hkl 
Estimated minimum and maximum transmission:  0.6895  0.7458 
The ratio (0.9245) of these values is more reliable than their absolute values 
Additional spherical absorption correction applied with mu*r =  0.2000 
Lambda/2 correction factor = 0.00150 
;
_shelx_res_checksum              88033
_shelx_hkl_checksum              57213