Stereospecific synthesis of alkyl-substituted vicinal diamines from the mother diamine: overcoming the "intrinsic barrier" to the diaza-Cope rearrangement reaction.
Kim, Hyunwoo; Staikova, Mima; Lough, Alan J.; Chin, Jik; Organic letters 11 (2009) 157–160; doi:10.1021/ol802496r

data_1503738
_publ_section_title
;
 Stereospecific synthesis of alkyl-substituted vicinal diamines from the
 mother diamine: overcoming the &quot;intrinsic barrier&quot; to the
 diaza-Cope rearrangement reaction.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              157
_journal_page_last               160
_journal_paper_doi               10.1021/ol802496r
_journal_volume                  11
_journal_year                    2009
_chemical_absolute_configuration rmad
_chemical_formula_moiety         '3(C14 H30 N2), 2(H3 O), 8(Cl)'
_chemical_formula_sum            'C42 H96 Cl8 N6 O2'
_chemical_formula_weight         998.82
_space_group_IT_number           199
_symmetry_cell_setting           cubic
_symmetry_space_group_name_Hall  'I 2b 2c 3'
_symmetry_space_group_name_H-M   'I 21 3'
_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            4
_cell_length_a                   17.9117(6)
_cell_length_b                   17.9117(6)
_cell_length_c                   17.9117(6)
_cell_measurement_reflns_used    5269
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      2.8
_cell_volume                     5746.6(3)
_computing_cell_refinement       'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius B.V., 1997-2002)'
_computing_data_reduction        Denzo-SMN
_computing_molecular_graphics    'SHELXTL V6.1'
_computing_publication_material  'SHELXTL V6.1'
_computing_structure_refinement  'SHELXTL V6.1(Sheldrick, 2001)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150(1)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_method       '\f scans and \w scans with \k offsets'
_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  0.0383
_diffrn_reflns_av_sigmaI/netI    0.0572
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            5269
_diffrn_reflns_theta_full        27.40
_diffrn_reflns_theta_max         27.40
_diffrn_reflns_theta_min         2.79
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.428
_exptl_absorpt_correction_T_max  0.920
_exptl_absorpt_correction_T_min  0.818
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.154
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2160
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.556
_refine_diff_density_min         -0.465
_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   0.03(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     93
_refine_ls_number_reflns         2166
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0468
_refine_ls_shift/su_max          0.027
_refine_ls_shift/su_mean         0.006
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0585P)^2^+3.3994P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1041
_refine_ls_wR_factor_ref         0.1177
_reflns_number_gt                1707
_reflns_number_total             2166
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ol802496r_si_001.cif
_cod_data_source_block           k06145
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Cubic' changed to 'cubic' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

2019-05-07
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     'C14 H30 Cl2 N2, 0.67H3 O, 0.67Cl'
_cod_original_formula_sum        'C14 H32 Cl2.67 N2 O0.67'
_cod_original_formula_units_Z    12
_cod_original_formula_weight     332.94
_cod_database_code               1503738