Carbon-Carbon Bond-Forming Reactions of α-Thioaryl Carbonyl Compounds for the Synthesis of Complex Heterocyclic Molecules
James E. Biggs-Houck; Rebecca L. Davis; Jingqiang Wei; Brandon Q. Mercado; Marilyn M. Olmstead; Dean J. Tantillo; Jared T. Shaw; Journal of Organic Chemistry 77 (2012) 160–172; doi:10.1021/jo201541e

data_4026826
_publ_section_title
;
 Carbon-Carbon Bond-Forming Reactions of \a-Thioaryl Carbonyl Compounds
 for the Synthesis of Complex Heterocyclic Molecules
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              160
_journal_page_last               172
_journal_paper_doi               10.1021/jo201541e
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C35 H31 Br2 N3 O3, H2 O'
_chemical_formula_sum            'C35 H33 Br2 N3 O4'
_chemical_formula_weight         719.48
_chemical_name_common
'Compound 51, Tricycle bis-p-bromophenylamide'
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 92.626(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.6340(4)
_cell_length_b                   16.3527(4)
_cell_length_c                   13.0268(3)
_cell_measurement_reflns_used    3251
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      50.43
_cell_measurement_theta_min      3.02
_cell_volume                     3114.11(13)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'Apex 2 (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      90(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Apex DUO'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0623
_diffrn_reflns_av_sigmaI/netI    0.0345
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            71832
_diffrn_reflns_theta_full        50.43
_diffrn_reflns_theta_max         50.43
_diffrn_reflns_theta_min         3.02
_exptl_absorpt_coefficient_mu    3.661
_exptl_absorpt_correction_T_max  0.610
_exptl_absorpt_correction_T_min  0.406
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'TWINABS (Sheldrick, 2003)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_description       'triangular plate'
_exptl_crystal_F_000             1464
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.702
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     403
_refine_ls_number_reflns         3251
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0445
_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^)+(0.0606P)^2^+6.8278P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1088
_refine_ls_wR_factor_ref         0.1144
_reflns_number_gt                2660
_reflns_number_total             3251
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo201541e_si_001_2.cif
_cod_data_source_block           bqm74
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4026826