Synthetic Application and Structural Elucidation of Axially Chiral Dicarboxylic Acid: Asymmetric Mannich-type Reaction with Diazoacetate, (Diazomethyl)phosphonate, and (Diazomethyl)sulfone
Takuya Hashimoto; Hidenori Kimura; Hiroki Nakatsu; Keiji Maruoka; Journal of Organic Chemistry 76 (2011) 6030–6037; doi:10.1021/jo2005999

data_4026476
_publ_section_title
;
 Synthetic Application and Structural Elucidation of Axially Chiral
 Dicarboxylic Acid: Asymmetric Mannich-type Reaction with Diazoacetate,
 (Diazomethyl)phosphonate, and (Diazomethyl)sulfone
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6030
_journal_page_last               6037
_journal_paper_doi               10.1021/jo2005999
_journal_volume                  76
_journal_year                    2011
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C57 H62 Cl4 N2 O4'
_chemical_formula_sum            'C57 H62 Cl4 N2 O4'
_chemical_formula_weight         980.94
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 93.6506(12)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   9.14269(17)
_cell_length_b                   9.68223(18)
_cell_length_c                   30.1893(6)
_cell_measurement_reflns_used    24656
_cell_measurement_temperature    123
_cell_measurement_theta_max      68.26
_cell_measurement_theta_min      4.41
_cell_volume                     2666.98(9)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 5.000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0717
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            31027
_diffrn_reflns_theta_full        68.25
_diffrn_reflns_theta_max         68.25
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.377
_exptl_absorpt_correction_T_max  0.788
_exptl_absorpt_correction_T_min  0.647
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_description       block
_exptl_crystal_F_000             1036.00
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         1.190
_refine_diff_density_min         -0.740
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  4367 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.05(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     613
_refine_ls_number_reflns         9542
_refine_ls_number_restraints     1
_refine_ls_R_factor_gt           0.0749
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.1360P)^2^+2.2330P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.2198
_reflns_number_gt                8884
_reflns_number_total             9542
_reflns_threshold_expression     F>2.0\s(F)
_cod_data_source_file            jo2005999_si_001.cif
_cod_data_source_block           0624-2
_cod_database_code               4026476