Stereospecific Synthesis of C2 Symmetric Diamines from the Mother Diamine by Resonance-Assisted Hydrogen-Bond Directed Diaza-Cope Rearrangement
Hyunwoo Kim; Yen Nguyen; Cindy Pai-Hui Yen; Leonid Chagal; Alan J. Lough; B. Moon Kim; Jik Chin; Journal of the American Chemical Society 130 (2008) 12184–12191; doi:10.1021/ja803951u

data_4108308
_publ_section_title
;
 Stereospecific Synthesis of C2 Symmetric Diamines from the Mother Diamine
 by Resonance-Assisted Hydrogen-Bond Directed Diaza-Cope Rearrangement
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12184
_journal_page_last               12191
_journal_paper_doi               10.1021/ja803951u
_journal_volume                  130
_journal_year                    2008
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C22 H22 N2, 4/3(C H4 O), 2(Cl)'
_chemical_formula_sum            'C23.33333 H27.33333 Cl2 N2 O1.33333'
_chemical_formula_weight         428.04
_space_group_IT_number           20
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'C 2c 2'
_symmetry_space_group_name_H-M   'C 2 2 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            12
_cell_length_a                   15.6507(7)
_cell_length_b                   22.6708(7)
_cell_length_c                   19.8315(10)
_cell_measurement_reflns_used    21262
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.6
_cell_volume                     7036.5(5)
_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    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXTL V6.1'
_computing_structure_refinement  'SHELXTL V6.1 (Sheldrick, 2008)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.102
_diffrn_reflns_av_sigmaI/netI    0.0815
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            22761
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.59
_exptl_absorpt_coefficient_mu    0.294
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_correction_T_min  0.665
_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    1.212
_exptl_crystal_description       needle
_exptl_crystal_F_000             2712
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.514
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.12(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     392
_refine_ls_number_reflns         6067
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.995
_refine_ls_R_factor_all          0.1101
_refine_ls_R_factor_gt           0.0652
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1082P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1608
_refine_ls_wR_factor_ref         0.1787
_reflns_number_gt                3899
_reflns_number_total             6067
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ja803951u-file001.cif
_cod_data_source_block           k07109
_cod_depositor_comments
;

2022-01-10
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '3(C22 H22 N2), 4(C H4 O), 6(Cl)'
_cod_original_formula_sum        'C70 H82 Cl6 N6 O4'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     1284.12
_cod_database_code               4108308