A series of boron difluoride complexes of azinylcarbazoles: synthesis and structure-property relationships.
Yamamoto, Koji; Matsui, Shun; Kato, Shin-Ichiro; Nakamura, Yosuke; Organic & biomolecular chemistry 21 (2023) 5398–5405; doi:10.1039/d3ob00795b

data_7159456
_publ_section_title
;
 A series of boron difluoride complexes of azinylcarbazoles: synthesis and
 structure-property relationships.
;
_journal_issue                   26
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5398
_journal_page_last               5405
_journal_paper_doi               10.1039/d3ob00795b
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C20 H13 B F2 N2'
_chemical_formula_sum            'C20 H13 B F2 N2'
_chemical_formula_weight         330.13
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-04-05
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-04-05 deposited with the CCDC.	2023-06-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.475(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4073(2)
_cell_length_b                   12.8859(3)
_cell_length_c                   15.5809(3)
_cell_measurement_reflns_used    20003
_cell_measurement_temperature    120
_cell_measurement_theta_max      29.9560
_cell_measurement_theta_min      2.6410
_cell_volume                     1480.41(6)
_computing_cell_refinement       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      120
_diffrn_detector                 PILT
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.921
_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   -103.00  77.00   0.25    5.00    --  -13.00  55.00 -36.00  720
  2  \w   -103.00  77.00   0.25    5.00    --  -13.00  55.00 108.00  720
  3  \w    -68.25  30.00   0.25    5.00    --  -13.00  55.00-108.00  393
  4  \w    -90.00 -29.00   0.25    5.00    --  -13.00  55.00  36.00  244
  5  \w    -99.00  -8.00   0.25    5.00    --  -13.00  27.00-180.00  364
  6  \w   -103.00 -38.00   0.25    5.00    --  -13.00  55.00-180.00  260
;
_diffrn_measurement_device       'AFC11 (Right): Eulerian 3 circle'
_diffrn_measurement_device_type  'Rigaku Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0391451000
_diffrn_orient_matrix_UB_12      0.0471536000
_diffrn_orient_matrix_UB_13      0.0162772000
_diffrn_orient_matrix_UB_21      -0.0260528000
_diffrn_orient_matrix_UB_22      0.0245670000
_diffrn_orient_matrix_UB_23      -0.0400015000
_diffrn_orient_matrix_UB_31      -0.0839015000
_diffrn_orient_matrix_UB_32      0.0143943000
_diffrn_orient_matrix_UB_33      0.0149796000
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_unetI/netI     0.0098
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            24291
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.905
_diffrn_reflns_theta_min         2.055
_diffrn_source                   'Rotating Anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60360
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.72a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3939
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0425
_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^)+(0.0749P)^2^+0.4532P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1204
_refine_ls_wR_factor_ref         0.1219
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3667
_reflns_number_total             3939
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00795b2.cif
_cod_data_source_block           fullconjugate_2_autored
_cod_database_code               7159456
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C20 H13 B F2 N2'
_chemical_oxdiff_usercomment     'Recryst. from CH2Cl2-Bu2O'
_reflns_odcompleteness_completeness 92.12
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     29.84
_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.a Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I),
 C00J(H00J), C00K(H00K), C00M(H00M), C00N(H00N)
2.b Idealised Me refined as rotating group:
 C00O(H00A,H00B,H00C)
;
_shelx_res_checksum              7886
_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 1.354
_oxdiff_exptl_absorpt_empirical_full_min 0.528