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_4109681
_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            'C17 H19 Cl N O7 P'
_chemical_formula_weight         415.75
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.5818(17)
_cell_length_b                   13.1046(15)
_cell_length_c                   9.3400(10)
_cell_measurement_reflns_used    5306
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      28.11
_cell_measurement_theta_min      2.54
_cell_volume                     1907.2(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      153(2)
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.965
_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  0.0386
_diffrn_reflns_av_sigmaI/netI    0.0272
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            15844
_diffrn_reflns_theta_full        28.22
_diffrn_reflns_theta_max         28.22
_diffrn_reflns_theta_min         2.54
_exptl_absorpt_coefficient_mu    0.324
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.556
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_meas      0
_exptl_crystal_description       Block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.549
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         2375
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.119
_refine_ls_R_factor_all          0.0910
_refine_ls_R_factor_gt           0.0720
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1134P)^2^+1.8053P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1978
_refine_ls_wR_factor_ref         0.2173
_reflns_number_gt                1748
_reflns_number_total             2375
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja071163rsi20070216_084220.cif
_cod_data_source_block           5b
_cod_database_code               4109681