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_4024053
_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 ad
_chemical_formula_moiety         'C9 H17 N4 , Cl'
_chemical_formula_sum            'C9 H17 Cl N4'
_chemical_formula_weight         216.72
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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            8
_cell_length_a                   9.0091(15)
_cell_length_b                   15.194(4)
_cell_length_c                   16.428(2)
_cell_measurement_reflns_used    143
_cell_measurement_temperature    163(2)
_cell_measurement_theta_max      23
_cell_measurement_theta_min      3
_cell_volume                     2248.7(8)
_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      163(2)
_diffrn_measured_fraction_theta_full 0.951
_diffrn_measured_fraction_theta_max 0.951
_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  0.0732
_diffrn_reflns_av_sigmaI/netI    0.0697
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            37125
_diffrn_reflns_theta_full        30.84
_diffrn_reflns_theta_max         30.84
_diffrn_reflns_theta_min         1.83
_diffrn_standards_decay_%        0.0
_diffrn_standards_interval_time  1200
_diffrn_standards_number         310
_exptl_absorpt_coefficient_mu    0.310
_exptl_absorpt_correction_T_max  0.954
_exptl_absorpt_correction_T_min  0.902
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   ' SHELXTL (Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.05(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         6551
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0947
_refine_ls_R_factor_gt           0.0461
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.04P)^2^+0.3P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0798
_refine_ls_wR_factor_ref         0.0937
_reflns_number_gt                4457
_reflns_number_total             6551
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo070534jsi20070315_055513.cif
_cod_data_source_block           4a
_cod_database_code               4024053