Iodine-Catalyzed Synthesis of <i>N,N</i>'-Chelate Organoboron Aminoquinolate.
Yang, Tianbao; Cao, Xin; Zhang, Xing-Xing; Ou, Yifeng; Au, Chak-Tong; Yin, Shuang-Feng; Qiu, Renhua; The Journal of organic chemistry 85 (2020) 12430–12443; doi:10.1021/acs.joc.0c01649

data_4038833
_publ_section_title
;
 Iodine-Catalyzed Synthesis of <i>N,N</i>'-Chelate Organoboron
 Aminoquinolate.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12430
_journal_page_last               12443
_journal_paper_doi               10.1021/acs.joc.0c01649
_journal_volume                  85
_journal_year                    2020
_chemical_formula_moiety         'C23 H16 B F3 N2 O'
_chemical_formula_sum            'C23 H16 B F3 N2 O'
_chemical_formula_weight         404.19
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-10-22
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2019.10.11 svn.r3662 for OlexSys, GUI svn.r5962)
;
_cell_angle_alpha                90
_cell_angle_beta                 105.707(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6380(9)
_cell_length_b                   16.4283(14)
_cell_length_c                   12.1516(13)
_cell_measurement_reflns_used    2377
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      27.8300
_cell_measurement_theta_min      2.4780
_cell_volume                     1852.2(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS n/a (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w     10.00  65.00   1.00    5.50    --  -11.59  19.00 -60.00   55
  2  \w    -89.00  59.00   1.00    5.50    --  -11.59   0.00 -90.00  148
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0706125000
_diffrn_orient_matrix_UB_12      0.0157547000
_diffrn_orient_matrix_UB_13      -0.0222338000
_diffrn_orient_matrix_UB_21      -0.0243206000
_diffrn_orient_matrix_UB_22      -0.0240073000
_diffrn_orient_matrix_UB_23      0.0395270000
_diffrn_orient_matrix_UB_31      0.0161818000
_diffrn_orient_matrix_UB_32      0.0323043000
_diffrn_orient_matrix_UB_33      0.0402207000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_av_unetI/netI     0.0626
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8292
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.137
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3270
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0812
_refine_ls_R_factor_gt           0.0656
_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^)+(0.0973P)^2^+0.7374P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1639
_refine_ls_wR_factor_ref         0.1791
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2568
_reflns_number_total             3270
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01649_si_004.cif
_cod_data_source_block           ytb
_cod_depositor_comments
'Adding full bibliography for 4038833--4038834.cif.'
_cod_database_code               4038833
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.986
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C19(H19), C13(H13), C17(H17), C20(H20), C7(H7), C23(H23), C21(H21), C16(H16),
 C1(H1), C22(H22), C2(H2), C3(H3), C9(H9), C15(H15), C14(H14), C8(H8)
;
_shelx_res_checksum              7924
_shelx_hkl_checksum              70746
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.825
_oxdiff_exptl_absorpt_empirical_full_min 0.573