Enantioselective Synthesis of Azoniahelicenes by Rh-Catalyzed C‒H Annulation with Alkynes
Wang, Qiang; Zhang, Wen-Wen; Zheng, Chao; Gu, Qing; You, Shu-Li; Journal of the American Chemical Society  (2020) –; doi:10.1021/jacs.0c11735

data_4135425
_publ_section_title
;
 Enantioselective Synthesis of Azoniahelicenes by Rh-Catalyzed C--H
 Annulation with Alkynes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.0c11735
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_sum            'C38 H24 F3 N O3 S'
_chemical_formula_weight         631.64
_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   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 109.901(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.6576(9)
_cell_length_b                   16.5515(15)
_cell_length_c                   10.2287(10)
_cell_measurement_reflns_used    6628
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      45.882
_cell_measurement_theta_min      4.901
_cell_volume                     1537.4(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      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0423
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            22666
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_min         2.449
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6645
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             652
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
; 
 Flack x determined using 1630 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.04(4)
_refine_ls_extinction_coef       0.033(6)
_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   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     488
_refine_ls_number_reflns         5715
_refine_ls_number_restraints     209
_refine_ls_restrained_S_all      1.184
_refine_ls_R_factor_all          0.0875
_refine_ls_R_factor_gt           0.0621
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0859P)^2^+0.4832P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1519
_refine_ls_wR_factor_ref         0.1736
_reflns_Friedel_coverage         0.928
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                4206
_reflns_number_total             5715
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c11735_si_002.cif
_cod_data_source_block           mo_d8v20454_0m
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4135425
_shelx_estimated_absorpt_t_min   0.971
_shelx_estimated_absorpt_t_max   0.989
_shelxl_version_number           2013-4
_shelx_res_checksum              75352
_shelx_hkl_checksum              43210