Palladium-Catalyzed Anilide ortho-Arylation and Subsequent One-Pot Cyclization to Phenanthridines
Dmitry Shabashov; Olafs Daugulis; Journal of Organic Chemistry 72 (2007) 7720–7725; doi:10.1021/jo701387m

data_4024205
_publ_section_title
;
 Palladium-Catalyzed Anilide ortho-Arylation and Subsequent
 One-Pot Cyclization to Phenanthridines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7720
_journal_page_last               7725
_journal_paper_doi               10.1021/jo701387m
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C19 H17 Cl F3 N O2'
_chemical_formula_weight         383.79
_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                 92.084(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.250(2)
_cell_length_b                   13.256(4)
_cell_length_c                   16.975(5)
_cell_measurement_reflns_used    2541
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      23.56
_cell_measurement_theta_min      1.95
_cell_volume                     1855.2(9)
_computing_cell_refinement       'SAINT v7.12A (Bruker-Nonius, 2004)'
_computing_data_collection       'APEX2 v1.0-27 (Bruker-Nonius, 2005)'
_computing_data_reduction        'SAINT v7.12A (Bruker-Nonius, 2004)'
_computing_structure_refinement  'SHELXL v6.12 (G.M. Sheldrick, 2001)'
_computing_structure_solution    'SHELXS v6.12 (G.M. Sheldrick, 2001)'
_diffrn_ambient_temperature      223(2)
_diffrn_detector_area_resol_mean 4K
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker-Nonius APEX II CCD'
_diffrn_measurement_method       CCD
_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  0.0698
_diffrn_reflns_av_sigmaI/netI    0.0332
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            8287
_diffrn_reflns_theta_full        23.56
_diffrn_reflns_theta_max         23.56
_diffrn_reflns_theta_min         1.95
_diffrn_standards_decay_%        0.0
_exptl_absorpt_coefficient_mu    0.247
_exptl_absorpt_correction_T_max  0.9669
_exptl_absorpt_correction_T_min  0.7262
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.485
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.930
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         2763
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.930
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0422
_refine_ls_shift/su_max          0.102
_refine_ls_shift/su_mean         0.008
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0652P)^2^+0.9457P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1067
_refine_ls_wR_factor_ref         0.1236
_reflns_number_gt                1649
_reflns_number_total             2903
_reflns_threshold_expression     >4sigma(I)
_cod_data_source_file            jo701387m-File003.cif
_cod_data_source_block           k1078
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Empirical' changed to
'empirical' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_original_formula_sum        'C19 H17 N O2 Cl F3'
_cod_database_code               4024205