Synthesis of fluorinated amphoteric organoborons via iodofluorination of alkynyl and alkenyl MIDA boronates.
Fan, Wen-Xin; Li, Ji-Lin; Lv, Wen-Xin; Yang, Ling; Li, Qingjiang; Wang, Honggen; Chemical communications (Cambridge, England) 56 (2020) 82–85; doi:10.1039/c9cc08386c

data_7125428
_publ_section_title
;
 Synthesis of fluorinated amphoteric organoborons via iodofluorination of
 alkynyl and alkenyl MIDA boronates.
;
_journal_issue                   1
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              82
_journal_page_last               85
_journal_paper_doi               10.1039/c9cc08386c
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C13 H12 B F I N O4'
_chemical_formula_sum            'C13 H12 B F I N O4'
_chemical_formula_weight         402.95
_chemical_name_systematic
(E)-8-(2-fluoro-1-iodo-2-phenylvinyl)-4-methyldihydro-4l4,8l4-[1,3,2]oxazaborolo[2,3-b][1,3,2]oxazaborole-2,6(3H,5H)-dione
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-02-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-07-24 deposited with the CCDC.	2019-11-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.2960(10)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   27.8895(3)
_cell_length_b                   6.86390(10)
_cell_length_c                   34.3921(3)
_cell_measurement_reflns_used    19863
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      76.6890
_cell_measurement_theta_min      3.2730
_cell_volume                     6350.48(13)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.965
_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    -61.00  28.00   0.50    0.05    --  -46.62  27.00 -49.00  178
  2  \w   -121.00 -32.00   0.50    0.05    --  -46.62 -27.00 148.00  178
  3  \w    -28.00  61.00   0.50    0.05    --   46.62 -27.00 148.00  178
  4  \w     33.00 122.00   0.50    0.05    --   46.62  27.00 -49.00  178
  5  \w   -175.00 -86.00   0.50    0.30    -- -100.00 -27.00 148.00  178
  6  \w   -114.00 -25.00   0.50    0.30    -- -100.00  27.00 -49.00  178
  7  \w     93.00 178.00   0.50    0.30    --  107.00  27.00 -49.00  170
  8  \w     32.00 121.00   0.50    0.30    --  107.00 -27.00 148.00  178
  9  \w     15.00  95.00   0.50    0.05    --   46.62-125.00-180.00  160
 10  \w     32.00 120.00   0.50    0.05    --   46.62  38.00 150.00  176
 11  \w   -124.00 -27.00   0.50    0.30    -- -100.00  77.00 -30.00  194
 12  \w     34.00 109.00   0.50    0.30    --  107.00 -94.00-150.00  150
 13  \w     34.00 109.00   0.50    0.30    --  107.00 -94.00 -60.00  150
 14  \w     34.00 109.00   0.50    0.30    --  107.00 -94.00 -30.00  150
 15  \w     92.00 178.00   0.50    0.30    --  107.00  30.00   0.00  172
 16  \w     34.00 109.00   0.50    0.30    --  107.00 -94.00 150.00  150
 17  \w     34.00 117.00   0.50    0.30    --  107.00-125.00 150.00  166
 18  \w     23.00  54.00   0.50    0.05    --   46.62  77.00  30.00   62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0557285000
_diffrn_orient_matrix_UB_12      -0.0519007000
_diffrn_orient_matrix_UB_13      0.0123200000
_diffrn_orient_matrix_UB_21      -0.0042155000
_diffrn_orient_matrix_UB_22      -0.0612098000
_diffrn_orient_matrix_UB_23      0.0420708000
_diffrn_orient_matrix_UB_31      -0.0125094000
_diffrn_orient_matrix_UB_32      -0.2095380000
_diffrn_orient_matrix_UB_33      -0.0153471000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            31719
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.014
_diffrn_reflns_theta_min         2.664
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    16.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.05743
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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    1.686
_exptl_crystal_description       needle
_exptl_crystal_F_000             3136
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.846
_refine_diff_density_min         -1.264
_refine_diff_density_rms         0.110
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         6495
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0310
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0425P)^2^+34.5070P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0820
_refine_ls_wR_factor_ref         0.0844
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6226
_reflns_number_total             6495
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc08386c2.cif
_cod_data_source_block           fanwx_190220_2
_cod_depositor_comments
'Adding full bibliography for 7125428--7125430.cif.'
_cod_database_code               7125428
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.296
_shelx_estimated_absorpt_t_min   0.086
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00I(H00H,H00I), C00K(H00A,H00B), C00O(H00J,H00K), C00T(H00F,H00G)
2.b Aromatic/amide H refined with riding coordinates:
 C00R(H00R), C00U(H00U), C00W(H00W), C00X(H00X), C00Y(H00Y), C010(H010),
 C011(H011), C012(H012), C013(H013), C014(H014)
2.c Idealised Me refined as rotating group:
 C00Q(H00C,H00D,H00E), C00S(H00L,H00M,H00N)
;
_shelx_res_checksum              64953
_shelx_fab_checksum              94122
_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 9.583
_oxdiff_exptl_absorpt_empirical_full_min 0.652