Chiral Phosphoric Acid-Catalyzed Synthesis of Fluorinated 5,6-Dihydroindolo[1,2- c]quinazolines with Quaternary Stereocenters.
Wang, Xin-Wei; Chen, Mu-Wang; Wu, Bo; Wang, Baomin; Zhou, Yong-Gui; The Journal of organic chemistry 84 (2019) 8300–8308; doi:10.1021/acs.joc.9b00985

data_4037578
_publ_section_title
;
 Chiral Phosphoric Acid-Catalyzed Synthesis of Fluorinated
 5,6-Dihydroindolo[1,2- c]quinazolines with Quaternary Stereocenters.
;
_journal_issue                   12
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8300
_journal_page_last               8308
_journal_paper_doi               10.1021/acs.joc.9b00985
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_sum            'C25 H21 F3 N2 O'
_chemical_formula_weight         422.43
_space_group_crystal_system      hexagonal
_space_group_IT_number           170
_space_group_name_Hall           'P 65'
_space_group_name_H-M_alt        'P 65'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            12
_cell_length_a                   9.9188(2)
_cell_length_b                   9.9188(2)
_cell_length_c                   74.552(2)
_cell_measurement_reflns_used    9786
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      131.147
_cell_measurement_theta_min      7.114
_cell_volume                     6352.0(2)
_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 0.975
_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           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0939
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       87
_diffrn_reflns_limit_l_min       -83
_diffrn_reflns_number            104377
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.498
_diffrn_reflns_theta_min         3.557
_exptl_absorpt_coefficient_mu    0.832
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.5903
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             2640
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
; 
 Flack x determined using 2458 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.04(6)
_refine_ls_extinction_coef       0.0031(2)
_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   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     588
_refine_ls_number_reflns         7424
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0432
_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^)+(0.0460P)^2^+1.2636P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0969
_refine_ls_wR_factor_ref         0.1092
_reflns_Friedel_coverage         0.973
_reflns_Friedel_fraction_full    0.965
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                5906
_reflns_number_total             7424
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00985_si_002.cif
_cod_data_source_block           cu_d8v18730_0m
_cod_depositor_comments
;

2020-08-12
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        6351.9(3)
_cod_original_formula_sum        'C50 H42 F6 N4 O2'
_cod_original_formula_units_Z    6
_cod_original_formula_weight     844.87
_cod_database_code               4037578
_shelx_estimated_absorpt_t_min   0.851
_shelx_estimated_absorpt_t_max   0.914
_shelxl_version_number           2013-4
_shelx_res_checksum              51318
_shelx_hkl_checksum              823