Diastereoselective Synthesis of Dibenzoazepines through Chelation on Palladium(IV) Intermediates.
Narbonne, Vanessa; Retailleau, Pascal; Maestri, Giovanni; Malacria, Max; Organic letters 16 (2014) 628–631; doi:10.1021/ol403525c

data_1513410
_publ_section_title
;
 Diastereoselective Synthesis of Dibenzoazepines through Chelation on
 Palladium(IV) Intermediates.
;
_journal_issue                   2
_journal_name_full               'Organic letters'
_journal_page_first              628
_journal_page_last               631
_journal_paper_doi               10.1021/ol403525c
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C21 H17 N'
_chemical_formula_sum            'C21 H17 N'
_chemical_formula_weight         283.36
_chemical_name_systematic
;
 8-methyl-5-phenyl-5H-dibenzo[c,e]azepine
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2012
_cell_angle_alpha                90
_cell_angle_beta                 97.477(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.507(3)
_cell_length_b                   27.831(5)
_cell_length_c                   7.592(3)
_cell_measurement_reflns_used    1449
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.350
_cell_measurement_theta_min      0.407
_cell_volume                     1572.7(9)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement
'SHELXL-2012 (Sheldrick, 2012); CRYSTALBUILDER (Welter, 2006)'
_computing_structure_solution    'SIR97 (Altomare et al, 1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Nonius kappa-CCD diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0174
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            11256
_diffrn_reflns_point_group_measured_fraction_full 0.924
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_theta_full        25.240
_diffrn_reflns_theta_max         25.400
_diffrn_reflns_theta_min         3.509
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Nonius Kappa CCD'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_description       cobbledstone
_exptl_crystal_F_000             600
_exptl_crystal_recrystallization_method
'Slow evaporation from a mixture of ethanol/dichloromethane solvent'
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.390
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 1077 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
 Not reliable for absolute structure determination in the case of 
 a noncentrosymetric crystal structure.
;
_refine_ls_abs_structure_Flack   0.1(10)
_refine_ls_extinction_coef       0.14(3)
_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   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2664
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0661
_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^)+(0.1121P)^2^+0.5419P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1684
_refine_ls_wR_factor_ref         0.1759
_reflns_Friedel_coverage         0.873
_reflns_Friedel_fraction_full    0.870
_reflns_Friedel_fraction_max     0.864
_reflns_number_gt                2460
_reflns_number_total             2670
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol403525c_si_001.cif
_cod_data_source_block           compound_2m
_cod_database_code               1513410
_shelx_estimated_absorpt_t_min   0.993
_shelx_estimated_absorpt_t_max   0.993
_shelxl_version_number           2012-9
_shelx_res_checksum              47738
_shelx_hkl_checksum              2477