Enantiomerically Pure Isophorone Diamine [3-(Aminomethyl)-3,5,5-trimethylcyclohexylamine]: A Chiral 1,4-Diamine Building Block Made Available on Large Scale
Albrecht Berkessel; Katrin Roland; Michael Schröder; Jörg M. Neudörfl; Johann Lex; Journal of Organic Chemistry 71 (2006) 9312–9318; doi:10.1021/jo0613737

data_4022134
_publ_section_title
;
 Enantiomerically Pure Isophorone Diamine
 [3-(Aminomethyl)-3,5,5-trimethylcyclohexylamine]: A Chiral
 1,4-Diamine Building Block Made Available on Large Scale
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9312
_journal_page_last               9318
_journal_paper_doi               10.1021/jo0613737
_journal_volume                  71
_journal_year                    2006
_chemical_formula_moiety
'C96 H106 Cl8 N8 Ni4 O9, C2 H6 O, C H Cl3, 7(H2 O)'
_chemical_formula_sum            'C99 H127 Cl11 N8 Ni4 O17'
_chemical_formula_weight         2325.88
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 108.161(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.8512(10)
_cell_length_b                   31.8301(10)
_cell_length_c                   20.5872(10)
_cell_measurement_reflns_used    49009
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.00
_cell_measurement_theta_min      1.22
_cell_volume                     11115.0(9)
_computing_cell_refinement       'Nonius DENZO'
_computing_data_collection       'Nonius COLLECT'
_computing_data_reduction        'Nonius DENZO'
_computing_molecular_graphics    'SCHAKAL99 (E. Keller 1999)'
_computing_publication_material  'PLATON (A. L. Spek 1980-2004)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       Phi/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  0.0662
_diffrn_reflns_av_sigmaI/netI    0.1155
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            49009
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.22
_exptl_absorpt_coefficient_mu    0.996
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             4848
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         2.478
_refine_diff_density_min         -1.040
_refine_diff_density_rms         0.166
_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     1265
_refine_ls_number_reflns         23327
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.1459
_refine_ls_R_factor_gt           0.0768
_refine_ls_shift/su_max          1.924
_refine_ls_shift/su_mean         0.035
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1535P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2244
_refine_ls_wR_factor_ref         0.2625
_reflns_number_gt                12888
_reflns_number_total             23327
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0613737si20060706_124154.cif
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4022134