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_7159455
_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         'C29 H29 B F2 N2'
_chemical_formula_sum            'C29 H29 B F2 N2'
_chemical_formula_weight         454.35
_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             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                 100.414(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.9381(5)
_cell_length_b                   9.9194(3)
_cell_length_c                   11.6477(3)
_cell_measurement_reflns_used    21378
_cell_measurement_temperature    130
_cell_measurement_theta_max      30.0800
_cell_measurement_theta_min      2.3410
_cell_volume                     2379.30(11)
_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      130
_diffrn_detector                 PILT
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.928
_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  55.00-108.00  720
  2  \w   -103.00  77.00   0.25    5.00    --  -13.00  55.00 108.00  720
  3  \w    -25.00  35.00   0.25    5.00    --  -13.00  27.00 -36.00  240
  4  \w    -87.00  49.00   0.25    5.00    --  -13.00  55.00  36.00  544
  5  \w   -103.00  14.00   0.25    5.00    --  -13.00  55.00 -36.00  468
;
_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      0.0024021000
_diffrn_orient_matrix_UB_12      -0.0011218000
_diffrn_orient_matrix_UB_13      0.0615311000
_diffrn_orient_matrix_UB_21      0.0343485000
_diffrn_orient_matrix_UB_22      0.0024943000
_diffrn_orient_matrix_UB_23      0.0069458000
_diffrn_orient_matrix_UB_31      -0.0011536000
_diffrn_orient_matrix_UB_32      0.0714276000
_diffrn_orient_matrix_UB_33      0.0007026000
_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  0.0252
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.928
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            39597
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.972
_diffrn_reflns_theta_min         2.716
_diffrn_source                   'Rotating Anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80676
_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 orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_description       plate
_exptl_crystal_F_000             960
_exptl_crystal_recrystallization_method 'Recryst. from toluene-hexane'
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         6427
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0423
_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^)+(0.0675P)^2^+0.5293P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1194
_refine_ls_wR_factor_ref         0.1238
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5406
_reflns_number_total             6427
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00795b2.cif
_cod_data_source_block           20180518_bf2_2q_autored
_cod_database_code               7159455
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C29 H29 B F2 N2'
_reflns_odcompleteness_completeness 92.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     29.91
_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. Others
 Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=1-FVAR(1)
 Sof(C00W)=Sof(H00S)=Sof(H00T)=Sof(H00U)=FVAR(1)
 Sof(C00Z)=Sof(H00Z)=Sof(HB)=Sof(HC)=1-FVAR(2)
 Sof(C00Y)=Sof(H00Y)=Sof(H)=Sof(HA)=FVAR(2)
 Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(H2C)=1-FVAR(3)
 Sof(C00X)=Sof(H00V)=Sof(H00W)=Sof(H00X)=FVAR(3)
3.a Aromatic/amide H refined with riding coordinates:
 C008(H008), C009(H009), C00E(H00E), C00I(H00I), C00K(H00K), C00L(H00L),
 C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q)
3.b Idealised Me refined as rotating group:
 C00S(H00A,H00B,H00C), C00T(H00D,H00F,H00G), C00U(H00H,H00J,H00R), C00W(H00S,
 H00T,H00U), C00X(H00V,H00W,H00X), C00Y(H00Y,H,HA), C1(H1A,H1B,H1C), C00Z(H00Z,
 HB,HC), C2(H2A,H2B,H2C)
;
_shelx_res_checksum              10798
_olex2_submission_original_sample_id 20180518_carbazoleBF2_2quinoline
_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 1.747
_oxdiff_exptl_absorpt_empirical_full_min 0.590