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_4023312
_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            'C33 H26 N2 S2'
_chemical_formula_weight         514.68
_space_group_IT_number           148
_symmetry_cell_setting           rhombohedral
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
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_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
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_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            18
_cell_length_a                   33.049(5)
_cell_length_b                   33.049(5)
_cell_length_c                   12.458(4)
_cell_measurement_reflns_used    835
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      21.58
_cell_measurement_theta_min      2.47
_cell_volume                     11784(4)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0859
_diffrn_reflns_av_sigmaI/netI    0.0499
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
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_diffrn_reflns_theta_full        22.46
_diffrn_reflns_theta_max         22.46
_diffrn_reflns_theta_min         1.23
_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_T_max  0.9886
_exptl_absorpt_correction_T_min  0.9221
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing, Acta Cryst. (1995) A51 33-38.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needles
_exptl_crystal_F_000             4860
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     438
_refine_ls_number_reflns         3410
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0426
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0460P)^2^+8.4667P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0854
_refine_ls_wR_factor_ref         0.0937
_reflns_number_gt                2554
_reflns_number_total             3410
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo702389v-File001_2.cif
_cod_data_source_block           afr3
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               4023312