Synthesis of chiral seven-membered cyclic sulfonamides through palladium-catalyzed arylation of cyclic imines
Zhao, Zi-Biao; Shi, Lei; Meng, Fan-Jie; Li, Yaming; Zhou, Yong-Gui; Organic Chemistry Frontiers 6 (2019) 1572–; doi:10.1039/C8QO01323C

data_1554572
_publ_section_title
;
 Synthesis of chiral seven-membered cyclic sulfonamides through
 palladium-catalyzed arylation of cyclic imines
;
_journal_issue                   10
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1572
_journal_paper_doi               10.1039/C8QO01323C
_journal_volume                  6
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_sum            'C19 H15 N O2 S'
_chemical_formula_weight         321.38
_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'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2018-11-06 deposited with the CCDC.	2019-03-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.787(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.0275(15)
_cell_length_b                   8.0254(17)
_cell_length_c                   12.699(3)
_cell_measurement_reflns_used    9676
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      54.894
_cell_measurement_theta_min      5.184
_cell_volume                     800.9(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker 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  0.0469
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13998
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         2.592
_exptl_absorpt_coefficient_mu    0.211
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6340
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
; 
 Flack x determined using 1372 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.05(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         3112
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0285
_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^)+(0.0469P)^2^+0.0462P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0777
_refine_ls_wR_factor_ref         0.0784
_reflns_Friedel_coverage         0.863
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                3036
_reflns_number_total             3112
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo01323c2.cif
_cod_data_source_block           mo_d8v18258_0m
_cod_original_cell_volume        800.8(3)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1554572
_shelx_estimated_absorpt_t_min   0.959
_shelx_estimated_absorpt_t_max   0.975
_shelxl_version_number           2013-4
_shelx_res_checksum              25920
_shelx_hkl_checksum              38102