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_4038834
_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         'C25 H17 B Br F3 N2 O4'
_chemical_formula_sum            'C25 H17 B Br F3 N2 O4'
_chemical_formula_weight         557.12
_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     dual
_audit_creation_date             2017-10-27
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 104.0760(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.3714(3)
_cell_length_b                   14.8912(2)
_cell_length_c                   9.21540(10)
_cell_measurement_reflns_used    6934
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.4680
_cell_measurement_theta_min      4.9390
_cell_volume                     2312.27(6)
_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 (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_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.973
_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    -42.00 -17.00   1.00    1.00    --  -41.11 -37.00 -60.00   25
  2  \w     32.00  77.00   1.00    1.00    --   41.11 -99.00 -60.00   45
  3  \w     23.00  60.00   1.00    1.00    --   41.11-125.00-150.00   37
  4  \w     71.00 118.00   1.00    1.00    --  106.95-122.00 -31.00   47
  5  \w     59.00  89.00   1.00    1.00    --  106.95 -94.00  30.00   30
  6  \w     35.00 133.00   1.00    1.00    --  106.95 -45.00   0.00   98
  7  \w    120.00 171.00   1.00    1.00    --  106.95  45.00-120.00   51
  8  \w    102.00 169.00   1.00    1.00    --  106.95 125.00 -60.00   67
  9  \w    106.00 177.00   1.00    1.00    --  106.95  30.00 150.00   71
 10  \w     53.00 107.00   1.00    1.00    --  106.95-125.00 -90.00   54
 11  \w     28.00  56.00   1.00    1.00    --  106.95 -94.00  30.00   28
 12  \w   -112.00 -85.00   1.00    1.00    --  -41.11 -37.00 -60.00   27
 13  \w   -112.00  -2.00   1.00    1.00    --  -41.11 -19.00   0.00  110
;
_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      -0.0898780000
_diffrn_orient_matrix_UB_12      0.0162916000
_diffrn_orient_matrix_UB_13      -0.0252907000
_diffrn_orient_matrix_UB_21      -0.0141629000
_diffrn_orient_matrix_UB_22      -0.1021513000
_diffrn_orient_matrix_UB_23      -0.0014747000
_diffrn_orient_matrix_UB_31      0.0089514000
_diffrn_orient_matrix_UB_32      0.0015172000
_diffrn_orient_matrix_UB_33      0.1704478000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            9108
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.568
_diffrn_reflns_theta_min         3.962
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.968
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64840
_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    1.600
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.686
_refine_diff_density_min         -0.528
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     356
_refine_ls_number_reflns         4541
_refine_ls_number_restraints     30
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0356
_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^)+(0.0575P)^2^+1.4421P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0942
_refine_ls_wR_factor_ref         0.0957
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4311
_reflns_number_total             4541
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01649_si_005.cif
_cod_data_source_block           exp_927
_cod_depositor_comments
'Adding full bibliography for 4038833--4038834.cif.'
_cod_database_code               4038834
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.717
_shelx_estimated_absorpt_t_min   0.681
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C25, F1A, F2A, F3
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C25, F2A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C25, F3
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C25 \\sim F1A \\sim F2A \\sim F3: within 2A with sigma of 0.005 and sigma for
terminal atoms of 0.01
C25 \\sim F2A: within 2A with sigma of 0.005 and sigma for terminal atoms of
0.01
C25 \\sim F3: within 2A with sigma of 0.005 and sigma for terminal atoms of 0.01
4. Others
 Sof(F1A)=1-FVAR(1)
 Sof(F1)=FVAR(1)
 Sof(F2A)=1-FVAR(2)
 Sof(F2)=FVAR(2)
 Sof(F3)=1-FVAR(3)
 Sof(F3A)=FVAR(3)
5.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C22(H22), C1(H1), C11(H11), C3(H3), C19(H19), C20(H20), C15(H15),
 C7(H7), C9(H9), C14(H14), C13(H13), C8(H8), C12(H12)
5.b Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.382
_oxdiff_exptl_absorpt_empirical_full_min 0.666