A Highly Stereoselective Metal-Free Hydrogenation of Diimines for the Synthesis of Cis-Vicinal Diamines.
Zhu, Xiaxia; Du, Haifeng; Organic letters 17 (2015) 3106–3109; doi:10.1021/acs.orglett.5b01380

data_1520068
_publ_section_title
;
 A Highly Stereoselective Metal-Free Hydrogenation of Diimines for the
 Synthesis of Cis-Vicinal Diamines.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              3106
_journal_page_last               3109
_journal_paper_doi               10.1021/acs.orglett.5b01380
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C26 H22 Br2 N2, 2(C3 H7 N O)'
_chemical_formula_sum            'C32 H36 Br2 N4 O2'
_chemical_formula_weight         668.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2014-11-24
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_cell_angle_alpha                90
_cell_angle_beta                 101.279(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.037(2)
_cell_length_b                   8.2451(18)
_cell_length_c                   18.991(5)
_cell_measurement_reflns_used    4436
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4832
_cell_measurement_theta_min      2.0689
_cell_volume                     1541.3(6)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2013)'
_computing_structure_solution
;
'SHELXS (Sheldrick, 2013)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0981
_diffrn_orient_matrix_UB_12      -0.0196
_diffrn_orient_matrix_UB_13      0.0175
_diffrn_orient_matrix_UB_21      0.0203
_diffrn_orient_matrix_UB_22      0.0050
_diffrn_orient_matrix_UB_23      0.1195
_diffrn_orient_matrix_UB_31      -0.0205
_diffrn_orient_matrix_UB_32      0.0496
_diffrn_orient_matrix_UB_33      0.0014
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            10413
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.477
_diffrn_reflns_theta_min         2.702
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    2.664
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7017
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_description       block
_exptl_crystal_F_000             684
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.787
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         3483
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.145
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0403
_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^)+(0.0356P)^2^+1.7513P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0940
_refine_ls_wR_factor_ref         0.0966
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3218
_reflns_number_total             3483
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b01380_si_002.cif
_cod_data_source_block           sa3728
_cod_depositor_comments          'Adding full bibliography for 1520068.cif.'
_cod_database_code               1520068
_shelxl_version_number           2013-4
_diffrn_number_total             3735
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C12(H12), C13(H13),
 C16(H16)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              33336
_shelx_hkl_checksum              60107