Photoinduced successive oxidative ring-opening and borylation of indolizines with NHC-boranes.
Zheng, Huitao; Xiong, Honggang; Su, Chaobo; Cao, Hua; Yao, Huagang; Liu, Xiang; RSC advances 12 (2021) 470–474; doi:10.1039/d1ra08072e

data_7244106
_publ_section_title
;
 Photoinduced successive oxidative ring-opening and borylation of
 indolizines with NHC-boranes.
;
_journal_issue                   1
_journal_name_full               'RSC advances'
_journal_page_first              470
_journal_page_last               474
_journal_paper_doi               10.1039/d1ra08072e
_journal_volume                  12
_journal_year                    2021
_chemical_formula_moiety         'C20 H21 B Cl N3 O2'
_chemical_formula_sum            'C20 H21 B Cl N3 O2'
_chemical_formula_weight         381.66
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-07-30
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_audit_update_record
;
2021-10-20 deposited with the CCDC.	2021-12-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.598(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.0381(3)
_cell_length_b                   20.5925(7)
_cell_length_c                   7.15692(19)
_cell_measurement_reflns_used    2474
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.3610
_cell_measurement_theta_min      4.0050
_cell_volume                     1920.79(9)
_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    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.967
_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      2.00  29.00   1.00    1.00    --   40.73 -99.00  60.00   27
  2  \w     31.00  81.00   1.00    1.00    --   40.73 -99.00  60.00   50
  3  \w     84.00 118.00   1.00    1.50    --  107.58-125.00  90.00   34
  4  \w     43.00 108.00   1.00    1.50    --  107.58 -95.00  90.00   65
  5  \w     34.00  79.00   1.00    1.50    --  107.58-125.00  90.00   45
  6  \w     86.00 170.00   1.00    1.50    --  107.58  45.00 -30.00   84
  7  \w    111.00 155.00   1.00    1.50    --  107.58 125.00 -82.00   44
  8  \w     94.00 177.00   1.00    1.50    --  107.58 125.00  60.00   83
  9  \w     82.00 149.00   1.00    1.50    --  107.58  45.00-150.00   67
 10  \w     23.00  68.00   1.00    1.00    --   40.73  38.00-180.00   45
 11  \w   -112.00 -28.00   1.00    1.00    --  -40.73 -57.00 -90.00   84
;
_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      -0.1005006000
_diffrn_orient_matrix_UB_12      -0.0393628000
_diffrn_orient_matrix_UB_13      -0.0059748000
_diffrn_orient_matrix_UB_21      0.0620107000
_diffrn_orient_matrix_UB_22      -0.0633758000
_diffrn_orient_matrix_UB_23      -0.0156359000
_diffrn_orient_matrix_UB_31      0.0051750000
_diffrn_orient_matrix_UB_32      -0.0057520000
_diffrn_orient_matrix_UB_33      0.2146530000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            3641
_diffrn_reflns_point_group_measured_fraction_full 0.678
_diffrn_reflns_point_group_measured_fraction_max 0.649
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.698
_diffrn_reflns_theta_min         4.014
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.920
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85239
_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    1.320
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.02(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         2528
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0346
_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^)+(0.0497P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0857
_refine_ls_wR_factor_ref         0.0880
_reflns_Friedel_coverage         0.338
_reflns_Friedel_fraction_full    0.360
_reflns_Friedel_fraction_max     0.329
_reflns_number_gt                2445
_reflns_number_total             2528
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ra08072e2.cif
_cod_data_source_block           2-477
_cod_depositor_comments          'Adding full bibliography for 7244106.cif.'
_cod_original_cell_volume        1920.80(10)
_cod_database_code               7244106
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.846
_shelx_estimated_absorpt_t_min   0.775
_reflns_odcompleteness_completeness 99.44
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.98(2)
 0.02(2)
2. Fixed Uiso
 At 1.2 times of:
  All B(H,H) groups, All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 B1(H1A,H1B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C13(H13),
 C15(H15), C16(H16)
3.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
;
_shelx_res_checksum              8878
_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 1.251
_oxdiff_exptl_absorpt_empirical_full_min 0.592