Enantioselective Synthesis of anti-1,2-Diamines by Cu-Catalyzed Reductive Couplings of Azadienes with Aldimines and Ketimines.
Shao, Xinxin; Li, Kangnan; Malcolmson, Steven J.; Journal of the American Chemical Society 140 (2018) 7083–7087; doi:10.1021/jacs.8b04750

data_4132547
_publ_section_title
;
 Enantioselective Synthesis of anti-1,2-Diamines by Cu-Catalyzed Reductive
 Couplings of Azadienes with Aldimines and Ketimines.
;
_journal_issue                   23
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7083
_journal_page_last               7087
_journal_paper_doi               10.1021/jacs.8b04750
_journal_volume                  140
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C34 H30 Br N2 O P'
_chemical_formula_sum            'C34 H30 Br N2 O P'
_chemical_formula_weight         593.48
_chemical_name_common            Shaoxx-2-214
_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'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.4874(2)
_cell_length_b                   19.8805(3)
_cell_length_c                   20.6103(3)
_cell_measurement_reflns_used    447
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      22.8405
_cell_measurement_theta_min      2.4305
_cell_volume                     5936.11(15)
_computing_cell_refinement       'APEX3 v2017.3-0 (Bruker AXS)'
_computing_data_collection       'Bruker Instrument Service v2013.12.0.0'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 833)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker-Nonius X8 Kappa APEX II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            57674
_diffrn_reflns_theta_full        27.13
_diffrn_reflns_theta_max         27.13
_diffrn_reflns_theta_min         1.98
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.468
_exptl_absorpt_correction_T_max  0.81
_exptl_absorpt_correction_T_min  0.75
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2448
_exptl_crystal_size_max          0.299
_exptl_crystal_size_mid          0.212
_exptl_crystal_size_min          0.148
_refine_diff_density_max         0.419
_refine_diff_density_min         -0.397
_refine_ls_abs_structure_details
;

Flack x determined using 4876 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.0062(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     711
_refine_ls_number_reflns         13136
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0280
_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^)+(0.0280P)^2^+1.0534P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0568
_refine_ls_wR_factor_ref         0.0589
_reflns_number_gt                11800
_reflns_number_total             13136
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b04750_si_001.cif
_cod_data_source_block           rds750
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               4132547
_shelx_res_checksum              29145
_shelx_hkl_checksum              7079