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_4135426
_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 rmad
_chemical_formula_moiety         'C36 H23 N O'
_chemical_formula_sum            'C36 H23 N O'
_chemical_formula_weight         485.55
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2020-09-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6626(3)
_cell_length_b                   15.2264(5)
_cell_length_c                   21.4966(7)
_cell_measurement_reflns_used    9962
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      54.965
_cell_measurement_theta_min      3.095
_cell_volume                     2508.09(15)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      172.99
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            20638
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.965
_diffrn_reflns_theta_min         3.094
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.382
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.6573
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1496 before and 0.0814 after correction. The Ratio of minimum to maximum transmission is 0.8755. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_description       block
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 1796 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.28(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         4740
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.130
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0394
_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^)+(0.0448P)^2^+0.5481P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.0981
_reflns_Friedel_coverage         0.734
_reflns_Friedel_fraction_full    0.982
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                4471
_reflns_number_total             4740
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c11735_si_003.cif
_cod_data_source_block           mj20544_0m
_cod_database_code               4135426
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.977
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C9(H9), C15(H15), C16(H16),
 C17(H17), C18(H18), C20(H20), C21(H21), C26(H26), C27(H27), C28(H28), C29(H29),
  C30(H30), C32(H32), C33(H33), C34(H34), C35(H35), C36(H36)
;
_shelx_res_checksum              79488
_shelx_hkl_checksum              60253
_olex2_submission_special_instructions 'No special instructions were received'