Synthesis of Enantiopure 1,2-Diaminobicyclo[2.2.2]octane Derivatives, C1-Symmetric Chiral 1,2-Diamines with a Rigid Bicyclic Backbone.
Milbeo, Pierre; Moulat, Laure; Didierjean, Claude; Aubert, Emmanuel; Martinez, Jean; Calmès, Monique; The Journal of organic chemistry  (2017) –; doi:10.1021/acs.joc.7b00122

data_4032192
_publ_section_title
;
 Synthesis of Enantiopure 1,2-Diaminobicyclo[2.2.2]octane Derivatives,
 C1-Symmetric Chiral 1,2-Diamines with a Rigid Bicyclic Backbone.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.7b00122
_journal_year                    2017
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C17 H18 N2 O3'
_chemical_formula_sum            'C17 H18 N2 O3'
_chemical_formula_weight         298.33
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.2759(2)
_cell_length_b                   9.9429(3)
_cell_length_c                   23.3483(6)
_cell_measurement_reflns_used    11928
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.443
_cell_measurement_theta_min      3.786
_cell_volume                     1456.95(7)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type
;
Dual Wavelength Diffractometer from Rigaku
;
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            11928
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.443
_diffrn_reflns_theta_min         3.786
_exptl_absorpt_coefficient_mu    0.768
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3030
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0392
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0484P)^2^+0.4837P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0983
_refine_ls_wR_factor_ref         0.1030
_reflns_Friedel_coverage         0.701
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                2800
_reflns_number_total             3030
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b00122_si_002.cif
_cod_data_source_block           compound-8
_cod_original_cell_volume        1456.94(7)
_cod_database_code               4032192
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              10748
_shelx_hkl_checksum              68002