One-Pot Synthesis of Dibenzo[ b, d]oxepines via Olefinic C-F Bond Functionalization and Intramolecular Pd-Catalyzed C-H Arylation.
Ausekle, Elina; Ehlers, Peter; Villinger, Alexander; Langer, Peter; The Journal of organic chemistry 83 (2018) 14195–14202; doi:10.1021/acs.joc.8b02374

data_4034839
_publ_section_title
;
 One-Pot Synthesis of Dibenzo[ b, d]oxepines via Olefinic C-F Bond
 Functionalization and Intramolecular Pd-Catalyzed C-H Arylation.
;
_journal_issue                   22
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              14195
_journal_page_last               14202
_journal_paper_doi               10.1021/acs.joc.8b02374
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C22 H17 F O2'
_chemical_formula_sum            'C22 H17 F O2'
_chemical_formula_weight         332.35
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.9528(12)
_cell_length_b                   8.6413(4)
_cell_length_c                   20.2208(12)
_cell_measurement_reflns_used    9946
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      28.73
_cell_measurement_theta_min      2.28
_cell_volume                     3311.7(3)
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_collection       'Bruker Apex V7.51A'
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_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 QUEST diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1505
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            86813
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_min         2.283
_diffrn_source                   'microfocus sealed tube'
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6538
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_description       needle
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3995
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0874
_refine_ls_R_factor_gt           0.0480
_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^)+(0.0440P)^2^+2.1797P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0998
_refine_ls_wR_factor_ref         0.1190
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2762
_reflns_number_total             3995
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02374_si_006.cif
_cod_data_source_block           is_ea722
_cod_database_code               4034839
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.970
_shelx_estimated_absorpt_t_max   0.995
_shelx_res_checksum              91491
_shelx_hkl_checksum              32614