Potassium tert-Butoxide-Catalyzed Synthesis of Benzofuroazepines via Cyclization of (2-Alkynylbenzyl)oxy Nitriles.
Gai, Rafaela; Back, Davi F.; Zeni, Gilson; The Journal of organic chemistry 80 (2015) 10278–10287; doi:10.1021/acs.joc.5b01884

data_4036416
_publ_section_title
;
 Potassium tert-Butoxide-Catalyzed Synthesis of Benzofuroazepines via
 Cyclization of (2-Alkynylbenzyl)oxy Nitriles.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10278
_journal_page_last               10287
_journal_paper_doi               10.1021/acs.joc.5b01884
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C22 H15 N O'
_chemical_formula_sum            'C22 H15 N O'
_chemical_formula_weight         309.35
_chemical_melting_point          ?
_chemical_name_common            6-phenyl-5H-benzo[d]benzofuro[3,2-b]azepine
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2015-07-15T15:14:15-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 118.336(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.3149(11)
_cell_length_b                   4.7459(3)
_cell_length_c                   18.9269(11)
_cell_measurement_reflns_used    4284
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.72
_cell_measurement_theta_min      2.396
_cell_volume                     1527.08(16)
_computing_cell_refinement       'BRUKER SANT'
_computing_data_collection       'Bruker Instrument Service v2012.10.0.0'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_molecular_graphics    'Diamond (version 3.2i; Crystal Impact GbR, Bo'
_computing_publication_material  'APEX2 (version 2012.10-0; Bruker, 2012)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXL97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker X8 Kappa APEX II diffractometer'
_diffrn_measurement_method       '0.5 \% \w & \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            19730
_diffrn_reflns_theta_full        27.19
_diffrn_reflns_theta_max         27.19
_diffrn_reflns_theta_min         2.15
_diffrn_source                   'sealed ceramic X ray tube'
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.9632
_exptl_absorpt_correction_T_min  0.9615
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS (version 2012/1; Bruker, 2012) was used to perform the numerical
        absorption correction based on the indexed faces of the crystal.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.03
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3374
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.03
_refine_ls_R_factor_all          0.07
_refine_ls_R_factor_gt           0.0405
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0414P)^2^+0.3183P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0879
_refine_ls_wR_factor_ref         0.1018
_reflns_number_gt                2327
_reflns_number_total             3374
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b01884_si_001.cif
_cod_data_source_block           p21c
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value 'none' was changed to '?'
-- the value is undefined or not given.

data item '_exptl_crystal_density_meas' value 'none' was changed to
'?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_Hall     -P2ybc
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4036416