One-pot synthesis of azabora[6]helicene by a Schiff base forming reaction.
Kage, Yuto; Jiang, Yuchuan; Minakuchi, Namiki; Mori, Shigeki; Shimizu, Soji; Chemical communications (Cambridge, England) 60 (2024) 3543–3546; doi:10.1039/d4cc00168k

data_7132782
_publ_section_title
;
 One-pot synthesis of azabora[6]helicene by a Schiff base forming
 reaction.
;
_journal_issue                   26
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3543
_journal_page_last               3546
_journal_paper_doi               10.1039/d4cc00168k
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C27 H15 B F N5'
_chemical_formula_sum            'C27 H15 B F N5'
_chemical_formula_weight         439.25
_chemical_name_systematic        'axially-fluoro-substituted azabora[6]helicene'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-12-21
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-12-21 deposited with the CCDC.	2024-03-01 downloaded from the CCDC.
;
_cell_angle_alpha                79.306(5)
_cell_angle_beta                 85.035(5)
_cell_angle_gamma                65.599(5)
_cell_formula_units_Z            2
_cell_length_a                   8.0536(5)
_cell_length_b                   8.9238(5)
_cell_length_c                   15.0934(9)
_cell_measurement_reflns_used    9636
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.7670
_cell_measurement_theta_min      2.5090
_cell_volume                     970.63(11)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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   -105.00  75.00   0.50    4.00    --  -15.00  45.00   0.00  360
  2  \w   -105.00  75.00   0.50    4.00    --  -15.00  45.00  90.00  360
  3  \w   -105.00  75.00   0.50    4.00    --  -15.00  45.00 180.00  360
  4  \w   -105.00  75.00   0.50    4.00    --  -15.00  45.00 270.00  360
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0695571000
_diffrn_orient_matrix_UB_12      -0.0769208000
_diffrn_orient_matrix_UB_13      -0.0083601000
_diffrn_orient_matrix_UB_21      0.0583097000
_diffrn_orient_matrix_UB_22      0.0075259000
_diffrn_orient_matrix_UB_23      0.0299270000
_diffrn_orient_matrix_UB_31      -0.0334068000
_diffrn_orient_matrix_UB_32      -0.0431037000
_diffrn_orient_matrix_UB_33      0.0363589000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0646
_diffrn_reflns_av_unetI/netI     0.0611
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            19008
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.990
_diffrn_reflns_theta_min         2.541
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77908
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_description       plate
_exptl_crystal_F_000             452
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       0.010(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4687
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0884
_refine_ls_R_factor_gt           0.0534
_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^)+(0.0593P)^2^+0.0520P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1158
_refine_ls_wR_factor_ref         0.1277
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3200
_reflns_number_total             4687
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc00168k2.cif
_cod_data_source_block           proffuruta
_cod_depositor_comments
'Adding full bibliography for 7132782--7132783.cif.'
_cod_database_code               7132782
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C27 H15 B1 F1 N5'
_shelx_estimated_absorpt_t_max   0.999
_shelx_estimated_absorpt_t_min   0.990
_reflns_odcompleteness_completeness 90.33
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.77
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C25(H25), C6(H6), C23(H23), C2(H2), C7(H7), C24(H24), C19(H19),
 C4(H4), C3(H3), C13(H13), C15(H15), C21(H21), C14(H14), C20(H20)
;
_shelx_res_checksum              20760
_shelx_hkl_checksum              5805
_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 2.305
_oxdiff_exptl_absorpt_empirical_full_min 0.542