Catalytic Enantioselective Synthesis of N-C Axially Chiral Sulfonamides through Chiral Palladium-Catalyzed N-Allylation.
Kikuchi, Yuki; Nakamura, Chisato; Matsuoka, Mizuki; Asami, Rina; Kitagawa, Osamu; The Journal of organic chemistry 84 (2019) 8112–8120; doi:10.1021/acs.joc.9b00989

data_4034651
_publ_section_title
;
 Catalytic Enantioselective Synthesis of N-C Axially Chiral Sulfonamides
 through Chiral Palladium-Catalyzed N-Allylation.
;
_journal_issue                   12
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8112
_journal_page_last               8120
_journal_paper_doi               10.1021/acs.joc.9b00989
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C26 H37 N O2 S'
_chemical_formula_weight         427.62
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7016(3)
_cell_length_b                   11.9655(3)
_cell_length_c                   20.8347(6)
_cell_measurement_reflns_used    422
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      21.3791
_cell_measurement_theta_min      2.3286
_cell_volume                     2418.59(12)
_computing_cell_refinement       'APEX3 v2017.3-0 (Bruker AXS)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 833)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_radiation_monochromator  'multilayered confocal mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            27105
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.59
_exptl_absorpt_coefficient_mu    0.155
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_process_details
;
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.174
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.347
_exptl_crystal_size_mid          0.256
_exptl_crystal_size_min          0.122
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.262
_refine_ls_abs_structure_details
;

Flack x determined using 1609 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4280
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0299
_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^)+(0.0480P)^2^+0.2712P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0766
_refine_ls_wR_factor_ref         0.0800
_reflns_number_gt                3972
_reflns_number_total             4280
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00989_si_002.cif
_cod_data_source_block           yk181212f
_cod_database_code               4034651
_shelx_res_checksum              92939
_shelx_hkl_checksum              50359