Cyclobutene Ring-Opening of Bicyclo[4.2.0]octa-1,6-dienes: Access to CF3-Substituted 5,6,7,8-Tetrahydro-1,7-naphthyridines
Artur K. Mailyan; Alexander S. Peregudov; Pierre H. Dixneuf; Christian Bruneau; Sergey N. Osipov; Journal of Organic Chemistry 77 (2012) 8518–8526; doi:10.1021/jo301501r

data_4027560
_publ_section_title
;
 Cyclobutene Ring-Opening of Bicyclo[4.2.0]octa-1,6-dienes: Access to
 CF3-Substituted 5,6,7,8-Tetrahydro-1,7-naphthyridines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8518
_journal_page_last               8526
_journal_paper_doi               10.1021/jo301501r
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C17 H14 F6 N2'
_chemical_formula_sum            'C17 H14 F6 N2'
_chemical_formula_weight         360.30
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 116.3980(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.7506(10)
_cell_length_b                   9.9723(8)
_cell_length_c                   13.5743(11)
_cell_measurement_reflns_used    309
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28
_cell_measurement_theta_min      3
_cell_volume                     1546.0(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX II'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX II CCD area detector''
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0595
_diffrn_reflns_av_sigmaI/netI    0.0351
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16679
_diffrn_reflns_theta_full        28.99
_diffrn_reflns_theta_max         28.99
_diffrn_reflns_theta_min         1.82
_exptl_absorpt_coefficient_mu    0.143
_exptl_absorpt_correction_T_max  0.965
_exptl_absorpt_correction_T_min  0.960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_description       prism
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.516
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         4106
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0482
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0919P)^2^+0.2477P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1339
_refine_ls_wR_factor_ref         0.1432
_reflns_number_gt                3329
_reflns_number_total             4106
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo301501r_si_001.cif
_cod_data_source_block           a
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4027560