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_7159454
_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                 108.450(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.7698(7)
_cell_length_b                   14.1930(5)
_cell_length_c                   12.6454(6)
_cell_measurement_reflns_used    13734
_cell_measurement_temperature    130
_cell_measurement_theta_max      29.6930
_cell_measurement_theta_min      2.9630
_cell_volume                     2344.3(2)
_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 0.929
_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 -36.00  720
  3  \w    -90.25  48.00   0.25    5.00    --  -13.00  55.00  36.00  553
  4  \w    -11.00  49.00   0.25    5.00    --  -13.00  55.00-108.00  240
  5  \w   -103.00  11.25   0.25    5.00    --  -13.00  55.00-180.00  457
;
_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      0.0108536000
_diffrn_orient_matrix_UB_12      0.0362621000
_diffrn_orient_matrix_UB_13      0.0406897000
_diffrn_orient_matrix_UB_21      0.0156443000
_diffrn_orient_matrix_UB_22      -0.0342863000
_diffrn_orient_matrix_UB_23      0.0428971000
_diffrn_orient_matrix_UB_31      0.0508203000
_diffrn_orient_matrix_UB_32      0.0027768000
_diffrn_orient_matrix_UB_33      -0.0019095000
_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  0.0467
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.929
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            39741
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.929
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.884
_diffrn_reflns_theta_min         2.870
_diffrn_source                   'Rotating Anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75342
_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    1.287
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         6294
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0730
_refine_ls_R_factor_gt           0.0483
_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^)+(0.0565P)^2^+0.6675P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1118
_refine_ls_wR_factor_ref         0.1209
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4636
_reflns_number_total             6294
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00795b2.cif
_cod_data_source_block           190708_yamakou_2_autored
_cod_original_cell_volume        2344.32(19)
_cod_database_code               7159454
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C29 H29 B F2 N2'
_reflns_odcompleteness_completeness 92.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     29.82
_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(C4A)=Sof(H4AA)=Sof(H4AB)=Sof(H4AC)=1-FVAR(1)
 Sof(C4)=Sof(H4A)=Sof(H4B)=Sof(H4C)=FVAR(1)
 Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(H1AC)=1-FVAR(2)
 Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=FVAR(2)
 Sof(C3A)=Sof(H3AA)=Sof(H3AB)=Sof(H3AC)=1-FVAR(3)
 Sof(C3)=Sof(H3A)=Sof(H3B)=Sof(H3C)=FVAR(3)
3.a Aromatic/amide H refined with riding coordinates:
 C006(H006), C009(H009), C00E(H00E), C00H(H00H), C00K(H00K), C00L(H00L),
 C00M(H00M), C00O(H00O), C00Q(H00Q), C00R(H00R), C00T(H00T)
3.b Idealised Me refined as rotating group:
 C00N(H00A,H00B,H00C), C00P(H00D,H00F,H00G), C00U(H00I,H00J,H00N), C1(H1A,H1B,
 H1C), C3(H3A,H3B,H3C), C4(H4A,H4B,H4C), C4A(H4AA,H4AB,H4AC), C1A(H1AA,H1AB,
 H1AC), C3A(H3AA,H3AB,H3AC)
;
_shelx_res_checksum              51591
_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 1.622
_oxdiff_exptl_absorpt_empirical_full_min 0.708