Enantioselective cross-coupling of meso-epoxides with aryl halides.
Zhao, Yang; Weix, Daniel J.; Journal of the American Chemical Society 137 (2015) 3237–3240; doi:10.1021/jacs.5b01909

data_4129401
_publ_section_title
;
 Enantioselective cross-coupling of meso-epoxides with aryl halides.
;
_journal_issue                   9
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3237
_journal_page_last               3240
_journal_paper_doi               10.1021/jacs.5b01909
_journal_volume                  137
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H19 N O3 S'
_chemical_formula_sum            'C17 H19 N O3 S'
_chemical_formula_weight         317.39
_chemical_name_common            weixyz01
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                79.339(3)
_cell_angle_beta                 82.318(3)
_cell_angle_gamma                65.198(3)
_cell_formula_units_Z            2
_cell_length_a                   9.0914(15)
_cell_length_b                   9.1163(15)
_cell_length_c                   10.4464(17)
_cell_measurement_reflns_used    4079
_cell_measurement_temperature    100.0(5)
_cell_measurement_theta_max      35.21
_cell_measurement_theta_min      2.47
_cell_volume                     770.8(2)
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2013)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SIR2011 (Burla et al., 2012)'
_diffrn_ambient_temperature      100.0(5)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD platform'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_unetI/netI     0.0784
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            29021
_diffrn_reflns_point_group_measured_fraction_full 0.945
_diffrn_reflns_point_group_measured_fraction_max 0.906
_diffrn_reflns_theta_full        37.785
_diffrn_reflns_theta_max         38.683
_diffrn_reflns_theta_min         1.988
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_T_max  0.7476
_exptl_absorpt_correction_T_min  0.6647
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2012)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_description       block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.553
_refine_diff_density_min         -0.665
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details
; 
 Flack x determined using 3936 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.06(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         15877
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.1006
_refine_ls_R_factor_gt           0.0634
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0649P)^2^+0.1780P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1366
_refine_ls_wR_factor_ref         0.1574
_reflns_Friedel_coverage         0.900
_reflns_Friedel_fraction_full    0.903
_reflns_Friedel_fraction_max     0.858
_reflns_number_gt                10865
_reflns_number_total             15877
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b01909_si_002.cif
_cod_data_source_block           weixyz01
_cod_database_code               4129401
_shelx_estimated_absorpt_t_min   0.953
_shelx_estimated_absorpt_t_max   0.965
_shelxl_version_number           2014-3
_shelx_res_checksum              52773
_shelx_hkl_checksum              42257