A palladium-catalyzed ring-expansion reaction of cyclobutanols with 2-haloanilines leading to benzazepines and quinolines.
Shen, Xiao-Qin; Yan, Xiao-Wei; Zhang, Xing-Guo; Chemical communications (Cambridge, England) 57 (2021) 10234–10237; doi:10.1039/d1cc04395a

data_7128950
_publ_section_title
;
 A palladium-catalyzed ring-expansion reaction of cyclobutanols with
 2-haloanilines leading to benzazepines and quinolines.
;
_journal_issue                   79
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              10234
_journal_page_last               10237
_journal_paper_doi               10.1039/d1cc04395a
_journal_volume                  57
_journal_year                    2021
_chemical_formula_sum            'C16 H11 N O'
_chemical_formula_weight         233.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2021-07-21 deposited with the CCDC.	2021-09-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.8630(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.91270(10)
_cell_length_b                   28.5829(8)
_cell_length_c                   10.3664(3)
_cell_measurement_reflns_used    4477
_cell_measurement_temperature    213(2)
_cell_measurement_theta_max      54.944
_cell_measurement_theta_min      4.858
_cell_volume                     1157.89(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      213(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8316
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.995
_diffrn_reflns_theta_min         4.000
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6321
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.029
_refine_ls_extinction_coef       0.068(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2255
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0360
_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^)+(0.0383P)^2^+0.2340P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0885
_refine_ls_wR_factor_ref         0.0940
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1933
_reflns_number_total             2255
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc04395a2.cif
_cod_data_source_block           mo_ddz21039_0m
_cod_depositor_comments          'Adding full bibliography for 7128950.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7128950
_shelx_estimated_absorpt_t_min   0.983
_shelx_estimated_absorpt_t_max   0.990
_shelxl_version_number           2013-4
_shelx_res_checksum              87013
_shelx_hkl_checksum              76917