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_4024206
_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            'C20 H17 N'
_chemical_formula_weight         271.35
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                86.010(3)
_cell_angle_beta                 89.132(3)
_cell_angle_gamma                88.626(3)
_cell_formula_units_Z            4
_cell_length_a                   8.378(2)
_cell_length_b                   10.646(2)
_cell_length_c                   16.160(3)
_cell_measurement_reflns_used    3881
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      23.57
_cell_measurement_theta_min      1.26
_cell_volume                     1437.2(5)
_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 0.975
_diffrn_measured_fraction_theta_max 0.975
_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  0.0286
_diffrn_reflns_av_sigmaI/netI    0.0148
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            6354
_diffrn_reflns_theta_full        23.57
_diffrn_reflns_theta_max         23.57
_diffrn_reflns_theta_min         1.26
_diffrn_standards_decay_%        0.0
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.9789
_exptl_absorpt_correction_T_min  0.8583
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'rectangular column'
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.005(5)
_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   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     382
_refine_ls_number_reflns         4180
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0737
_refine_ls_R_factor_gt           0.0650
_refine_ls_shift/su_max          0.063
_refine_ls_shift/su_mean         0.016
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1165P)^2^+1.3166P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2053
_refine_ls_wR_factor_ref         0.2140
_reflns_number_gt                3200
_reflns_number_total             4200
_reflns_threshold_expression     >4sigma(I)
_cod_data_source_file            jo701387m-File004.cif
_cod_data_source_block           k1061
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_database_code               4024206