Synthesis of Tetra-ortho-substituted, Phosphorus-Containing and Carbonyl-Containing Biaryls Utilizing a Diels-Alder Approach
Bradley O. Ashburn; Rich G. Carter; Lev N. Zakharov; Journal of the American Chemical Society 129 (2007) 9109–9116; doi:10.1021/ja071163r

data_4109690
_publ_section_title
;
 Synthesis of Tetra-ortho-substituted, Phosphorus-Containing and
 Carbonyl-Containing Biaryls Utilizing a Diels-Alder Approach
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9109
_journal_page_last               9116
_journal_paper_doi               10.1021/ja071163r
_journal_volume                  129
_journal_year                    2007
_chemical_formula_sum            'C14 H10 Br N O2'
_chemical_formula_weight         304.14
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 100.856(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.788(2)
_cell_length_b                   9.0708(18)
_cell_length_c                   14.037(3)
_cell_measurement_reflns_used    5869
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.76
_cell_measurement_theta_min      2.34
_cell_volume                     1224.0(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      173(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0244
_diffrn_reflns_av_sigmaI/netI    0.0196
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13448
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.34
_exptl_absorpt_coefficient_mu    3.350
_exptl_absorpt_correction_T_max  0.9062
_exptl_absorpt_correction_T_min  0.4880
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.651
_exptl_crystal_density_meas      0
_exptl_crystal_description       plate
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.865
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2789
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0386
_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^)+(0.0395P)^2^+4.3462P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1039
_reflns_number_gt                2540
_reflns_number_total             2789
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja071163rsi20070508_072719.cif
_cod_data_source_block           52
_cod_original_cell_volume        1223.9(4)
_cod_database_code               4109690