A new approach to 10-arylated 5<i>H</i>-dibenzo[<i>b</i>,<i>f</i>]azepines using <i>syn</i>-selective hydrohalogenation of ethynylaniline.
Iwai, Kento; Mukaijo, Yusuke; Asahara, Haruyasu; Nishiwaki, Nagatoshi; Organic & biomolecular chemistry 20 (2022) 5543–5550; doi:10.1039/d2ob00950a

data_7158747
_publ_section_title
;
 A new approach to 10-arylated
 5<i>H</i>-dibenzo[<i>b</i>,<i>f</i>]azepines using <i>syn</i>-selective
 hydrohalogenation of ethynylaniline.
;
_journal_issue                   28
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5543
_journal_page_last               5550
_journal_paper_doi               10.1039/d2ob00950a
_journal_volume                  20
_journal_year                    2022
_chemical_formula_moiety         'C16 H13 Br2 N1 O1'
_chemical_formula_sum            'C16 H13 Br2 N O'
_chemical_formula_weight         395.07
_chemical_melting_point          389.1(3)
_chemical_name_systematic
E-1-(2-acetylaminophenyl)-1-bromo-2-(2-bromophenyl)ethene
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-02-08 deposited with the CCDC.	2022-06-29 downloaded from the CCDC.
;
_cell_angle_alpha                106.052(2)
_cell_angle_beta                 102.529(2)
_cell_angle_gamma                106.772(2)
_cell_formula_units_Z            4
_cell_length_a                   9.9894(2)
_cell_length_b                   11.4609(3)
_cell_length_c                   14.7673(4)
_cell_measurement_reflns_used    9984
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      29.4400
_cell_measurement_theta_min      2.0200
_cell_volume                     1472.53(7)
_computing_cell_refinement       'CrysAlisPro 1.171.40.47a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.47a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.47a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_computing_publication_material  'Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_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       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16132
_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         25.497
_diffrn_reflns_theta_min         1.992
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    5.499
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.116
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.47a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
   a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.782
_exptl_crystal_description       plate
_exptl_crystal_F_000             776
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Hexane'
_exptl_crystal_size_max          0.592
_exptl_crystal_size_mid          0.214
_exptl_crystal_size_min          0.076
_refine_diff_density_max         0.983
_refine_diff_density_min         -0.501
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         5481
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0320
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0486P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0754
_refine_ls_wR_factor_ref         0.0784
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4651
_reflns_number_total             5481
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00950a2.cif
_cod_data_source_block           5_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '388.8-389.5' was changed
to '389.1(3)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7158747--7158749.cif.
;
_cod_original_formula_sum        'C16 H13 Br2 N1 O1'
_cod_database_code               7158747
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              30556