Synthesis and Electronic Properties of Sterically Demanding N-Arylphenothiazines and Unexpected Buchwald-Hartwig Aminations
Adam W. Franz; Frank Rominger; Thomas J. J. Müller; Journal of Organic Chemistry 73 (2008) 1795–1802; doi:10.1021/jo702389v

data_4023314
_publ_contact_author_address
;
        Institut f\"ur Makromolekulare Chemie und Organische Chemie
        Heinrich-Heine-Universit\"at D\"usseldorf
        Universit\"atsstrasse 1
        D-40225 D\"usseldorf
        Germany
;
_publ_contact_author_email       ThomasJJ.Mueller@uni-duesseldorf.de
_publ_contact_author_fax         '+49 211 - 8114324'
_publ_contact_author_name        'M\"uller, Thomas J.J.'
_publ_contact_author_phone       '+49 211 - 8112298'
_publ_section_title
;
 Synthesis and Electronic Properties of Sterically Demanding
 N-Arylphenothiazines and Unexpected Buchwald-Hartwig Aminations
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1795
_journal_page_last               1802
_journal_paper_doi               10.1021/jo702389v
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C37 H40 N S'
_chemical_formula_weight         530.76
_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                83.976(5)
_cell_angle_beta                 84.600(5)
_cell_angle_gamma                74.742(5)
_cell_formula_units_Z            2
_cell_length_a                   9.091(2)
_cell_length_b                   9.227(2)
_cell_length_c                   18.537(4)
_cell_measurement_reflns_used    2080
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.07
_cell_measurement_theta_min      2.21
_cell_volume                     1488.3(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_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, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and 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  0.048
_diffrn_reflns_av_sigmaI/netI    0.064
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9661
_diffrn_reflns_theta_full        22.46
_diffrn_reflns_theta_max         22.46
_diffrn_reflns_theta_min         1.11
_exptl_absorpt_coefficient_mu    0.135
_exptl_absorpt_correction_T_max  0.9933
_exptl_absorpt_correction_T_min  0.9788
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing, Acta Cryst. (1995) A51 33-38.'
_exptl_crystal_colour            yellow-orange
_exptl_crystal_density_diffrn    1.184
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             570
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     512
_refine_ls_number_reflns         3862
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0834
_refine_ls_R_factor_gt           0.0555
_refine_ls_shift/su_max          0.075
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0486P)^2^+0.3021P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1093
_refine_ls_wR_factor_ref         0.1180
_reflns_number_gt                2871
_reflns_number_total             3862
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo702389v-File001_4.cif
_cod_data_source_block           afr5
_cod_database_code               4023314