Ring-opening fluorination of bicyclic azaarenes
Komatsuda, Masaaki; Suto, Ayane; Kondo, Hiroki; Takada, Hiroyuki; Kato, Kenta; Saito, Bunnai; Yamaguchi, Junichiro; Chemical Science 13 (2022) 665–670; doi:10.1039/D1SC06273E

data_1565909
_publ_section_title
;
 Ring-opening fluorination of bicyclic azaarenes
;
_journal_issue                   3
_journal_name_full               'Chemical Science'
_journal_page_first              665
_journal_page_last               670
_journal_paper_doi               10.1039/D1SC06273E
_journal_volume                  13
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C12 H9 Br F N3 O'
_chemical_formula_sum            'C12 H9 Br F N3 O'
_chemical_formula_weight         310.13
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-09-27
_audit_creation_method
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6380)
;
_audit_update_record
;
2021-11-04 deposited with the CCDC.	2021-12-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.671(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.0916(6)
_cell_length_b                   6.0738(5)
_cell_length_c                   12.9097(10)
_cell_measurement_reflns_used    4610
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      136.47
_cell_measurement_theta_min      7.11
_cell_volume                     610.89(9)
_computing_cell_refinement       'Rigaku RAPID-AUTO'
_computing_data_collection       'Rigaku RAPID-AUTO'
_computing_data_reduction        'Rigaku RAPID-AUTO'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  RAPID
_diffrn_measurement_method       'w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7095
_diffrn_reflns_point_group_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        67.680
_diffrn_reflns_theta_max         68.228
_diffrn_reflns_theta_min         3.556
_diffrn_source_current           100.0
_diffrn_source_power             5.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    4.651
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.6435
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'JABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.686
_exptl_crystal_description       block
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.405
_refine_diff_density_min         -1.047
_refine_diff_density_rms         0.151
_refine_ls_abs_structure_details
;
 Flack x determined using 868 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.031(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2127
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.147
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0323
_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^)+(0.0554P)^2^+0.0210P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0846
_refine_ls_wR_factor_ref         0.0847
_reflns_Friedel_coverage         0.725
_reflns_Friedel_fraction_full    0.894
_reflns_Friedel_fraction_max     0.890
_reflns_number_gt                2108
_reflns_number_total             2127
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc06273e2.cif
_cod_data_source_block           10
_cod_depositor_comments          'Adding full bibliography for 1565909.cif.'
_cod_database_code               1565909
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C2(H2), C5(H5), C3(H3), C11(H11), C10(H10), C12(H12)
1.b X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
;
_shelx_res_checksum              8419
_shelx_hkl_checksum              18946
_olex2_submission_special_instructions 'No special instructions were received'