Synthesis of C~2~-Symmetric Bisamidines: A New Type of Chiral Metal-Free Lewis Acid Analogue Interacting with Carbonyl Groups
Deniz Akalay; Gerd Dürner; Jan W. Bats; Michael Bolte; Michael W. Göbel; Journal of Organic Chemistry 72 (2007) 5618–5624; doi:10.1021/jo070534j

data_4024054
_publ_section_title
;
 Synthesis of C~2~-Symmetric Bisamidines: A New Type of Chiral
 Metal-Free Lewis Acid Analogue Interacting with Carbonyl Groups
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5618
_journal_page_last               5624
_journal_paper_doi               10.1021/jo070534j
_journal_volume                  72
_journal_year                    2007
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C31 H30 N4, 2(C6 H2 N3 O7)'
_chemical_formula_sum            'C43 H34 N10 O14'
_chemical_formula_weight         914.80
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 111.22(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   13.068(5)
_cell_length_b                   12.860(3)
_cell_length_c                   13.187(3)
_cell_measurement_reflns_used    66
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      23
_cell_measurement_theta_min      3
_cell_volume                     2065.8(10)
_computing_cell_refinement       'SMART (Siemens, 1995)'
_computing_data_collection       'SMART (Siemens, 1995)'
_computing_data_reduction        'SAINT (Siemens, 1995)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.952
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_device_type  SIEMENS_SMART_1K_CCD
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0979
_diffrn_reflns_av_sigmaI/netI    0.1106
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            24741
_diffrn_reflns_theta_full        27.85
_diffrn_reflns_theta_max         27.85
_diffrn_reflns_theta_min         1.67
_diffrn_standards_decay_%        0.0
_diffrn_standards_interval_time  1200
_diffrn_standards_number         156
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.870
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   ' SADABS (Sheldrick, 2000)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             948
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.0075(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     621
_refine_ls_number_reflns         4923
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.1305
_refine_ls_R_factor_gt           0.0500
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.03P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0689
_refine_ls_wR_factor_ref         0.0843
_reflns_number_gt                2809
_reflns_number_total             4923
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo070534jsi20070315_055545.cif
_cod_data_source_block           5f-dipicrate
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4024054