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_7132783
_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         'C H2 Cl2, C33 H20 B N5'
_chemical_formula_sum            'C34 H22 B Cl2 N5'
_chemical_formula_weight         582.27
_chemical_name_systematic        'axially-phenyl-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
_atom_sites_solution_secondary   difmap
_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                91.141(4)
_cell_angle_beta                 105.751(4)
_cell_angle_gamma                90.019(4)
_cell_formula_units_Z            2
_cell_length_a                   9.3419(4)
_cell_length_b                   10.0645(5)
_cell_length_c                   14.7904(6)
_cell_measurement_reflns_used    12630
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.7140
_cell_measurement_theta_min      2.2450
_cell_volume                     1338.11(11)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_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
_diffrn_detector_area_resol_mean 7.111
_diffrn_detector_type            'Rigaku Saturn724+ area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_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 1.00 -- -15.00 45.00 0.00 360
 2 \w -105.00 75.00 0.50 1.00 -- -15.00 45.00 90.00 360
 3 \w -105.00 75.00 0.50 1.00 -- -15.00 45.00 180.00 360
 4 \w -105.00 75.00 0.50 1.00 -- -15.00 45.00 270.00 360
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Varimax with Saturn'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0685389000
_diffrn_orient_matrix_UB_12      0.0205901000
_diffrn_orient_matrix_UB_13      0.0075198000
_diffrn_orient_matrix_UB_21      0.0225144000
_diffrn_orient_matrix_UB_22      0.0673781000
_diffrn_orient_matrix_UB_23      0.0004492000
_diffrn_orient_matrix_UB_31      -0.0319256000
_diffrn_orient_matrix_UB_32      0.0022754000
_diffrn_orient_matrix_UB_33      -0.0492661000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0624
_diffrn_reflns_av_unetI/netI     0.0581
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            25738
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.283
_diffrn_reflns_theta_min         2.024
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'MicroMax 007'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.279
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77017
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_description       plate
_exptl_crystal_F_000             600
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         6621
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0562
_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^)+(0.0691P)^2^+0.4965P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1327
_refine_ls_wR_factor_ref         0.1447
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5018
_reflns_number_total             6621
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc00168k2.cif
_cod_data_source_block           shimizu_autored
_cod_depositor_comments
'Adding full bibliography for 7132782--7132783.cif.'
_cod_database_code               7132783
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C33 H20 B1 N5'
_shelx_estimated_absorpt_t_max   0.994
_shelx_estimated_absorpt_t_min   0.936
_reflns_odcompleteness_completeness 87.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.67
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C34(H34A,H34B)
2.b Aromatic/amide H refined with riding coordinates:
 C25(H25), C4(H4), C15(H15), C2(H2), C24(H24), C3(H3), C14(H14), C13(H13),
 C33(H33), C8(H8), C6(H6), C29(H29), C19(H19), C23(H23), C21(H21), C7(H7),
 C32(H32), C30(H30), C20(H20), C31(H31)
;
_shelx_res_checksum              30905
_shelx_hkl_checksum              24909
_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 1.658
_oxdiff_exptl_absorpt_empirical_full_min 0.550