Iridium-Catalyzed Anti-Stereoselective Asymmetric Ring-Opening Reactions of Azabenzonorbornadienes with Carboxylic Acids.
Zhu, Meina; Chen, Jingchao; He, Xiaobo; Gu, Cuiping; Xu, Jianbin; Fan, Baomin; The Journal of organic chemistry 82 (2017) 3167–3172; doi:10.1021/acs.joc.7b00178

data_4032424
_publ_section_title
;
 Iridium-Catalyzed Anti-Stereoselective Asymmetric Ring-Opening Reactions
 of Azabenzonorbornadienes with Carboxylic Acids.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3167
_journal_page_last               3172
_journal_paper_doi               10.1021/acs.joc.7b00178
_journal_volume                  82
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H25 N O4'
_chemical_formula_sum            'C23 H25 N O4'
_chemical_formula_weight         379.44
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6023(8)
_cell_length_b                   11.2451(9)
_cell_length_c                   19.0201(15)
_cell_measurement_reflns_used    9473
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.18
_cell_measurement_theta_min      4.57
_cell_volume                     2053.8(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-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.937
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_Laue_measured_fraction_full 0.937
_diffrn_reflns_Laue_measured_fraction_max 0.923
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10276
_diffrn_reflns_point_group_measured_fraction_full 0.916
_diffrn_reflns_point_group_measured_fraction_max 0.897
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.390
_diffrn_reflns_theta_min         4.568
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.676
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_description       prism
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.750
_exptl_crystal_size_mid          0.410
_exptl_crystal_size_min          0.410
_exptl_transmission_factor_max   0.7532
_exptl_transmission_factor_min   0.5260
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.085
_refine_ls_abs_structure_details
;
 Flack x determined using 1394 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3449
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0458
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0961P)^2^+0.2771P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1287
_refine_ls_wR_factor_ref         0.1289
_reflns_Friedel_coverage         0.698
_reflns_Friedel_fraction_full    0.887
_reflns_Friedel_fraction_max     0.863
_reflns_number_gt                3430
_reflns_number_total             3449
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b00178_si_002.cif
_cod_data_source_block           cu_zmn34_0m
_cod_database_code               4032424
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.631
_shelx_estimated_absorpt_t_max   0.769
_shelx_res_checksum              42933
_shelx_hkl_checksum              46996