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_4034842
_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         'C18 H18 N2 O2, 3(H2 O)'
_chemical_formula_sum            'C18 H18 N2 O5'
_chemical_formula_weight         342.34
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.7883(4)
_cell_length_b                   11.6157(6)
_cell_length_c                   18.1845(10)
_cell_measurement_reflns_used    9885
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      32.25
_cell_measurement_theta_min      3.15
_cell_volume                     1645.09(15)
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_collection       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_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 0.997
_diffrn_measured_fraction_theta_max 0.998
_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  0.0633
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            58987
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.496
_diffrn_reflns_theta_min         3.149
_diffrn_source                   'microfocus sealed tube'
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_correction_T_min  0.7146
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2014)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.2(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         5942
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0447
_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^)+(0.0548P)^2^+0.2564P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0948
_refine_ls_wR_factor_ref         0.1014
_reflns_Friedel_coverage         0.947
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                5047
_reflns_number_total             5942
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02374_si_007.cif
_cod_data_source_block           is_ea7131001
_cod_database_code               4034842
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.965
_shelx_estimated_absorpt_t_max   0.994
_shelx_res_checksum              15141
_shelx_hkl_checksum              32958