Palladium-Catalyzed Dearomative syn-1,4-Diamination.
Wertjes, William C.; Okumura, Mikiko; Sarlah, David; Journal of the American Chemical Society 141 (2019) 163–167; doi:10.1021/jacs.8b13030

data_4133661
_publ_section_title
;
 Palladium-Catalyzed Dearomative syn-1,4-Diamination.
;
_journal_issue                   1
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              163
_journal_page_last               167
_journal_paper_doi               10.1021/jacs.8b13030
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C21 H22 N4 O2'
_chemical_formula_sum            'C21 H22 N4 O2'
_chemical_formula_weight         362.42
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-09-10
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                99.9720(10)
_cell_angle_beta                 104.3150(10)
_cell_angle_gamma                91.5190(10)
_cell_formula_units_Z            4
_cell_length_a                   9.5948(2)
_cell_length_b                   12.3669(3)
_cell_length_c                   16.3965(4)
_cell_measurement_reflns_used    19360
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.40
_cell_measurement_theta_min      2.83
_cell_volume                     1851.78(8)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.03
_diffrn_detector                 'Bruker Photon 100 area detector'
_diffrn_detector_type            'photon counter area detector'
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture/Photon 100'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            27751
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.398
_diffrn_reflns_theta_min         2.830
_diffrn_source_target            Cu
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.692
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6903
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0841 before and 0.0565 after correction. The Ratio of minimum to maximum transmission is 0.9166. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_description       plate
_exptl_crystal_F_000             768
_exptl_crystal_recrystallization_method
'Crystallization was conducted by slow diffusion in hexane /ethyl acetate.'
_exptl_crystal_size_max          0.143
_exptl_crystal_size_mid          0.129
_exptl_crystal_size_min          0.048
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0068(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     498
_refine_ls_number_reflns         6678
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0365
_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^)+(0.0268P)^2^+0.9388P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0805
_refine_ls_wR_factor_ref         0.0851
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5808
_reflns_number_total             6678
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b13030_si_004.cif
_cod_data_source_block           cu_dd23k_0m
_cod_database_code               4133661
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.968
_shelx_estimated_absorpt_t_min   0.908
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C4(H4), C22(H22), C25(H25)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14a,H14b), C35(H35a,H35b)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2a), C3(H3), C6(H6), C7(H7), C8(H8), C9(H9), C16(H16), C17(H17), C18(H18),
  C19(H19), C20(H20), C23(H23), C24(H24), C27(H27), C28(H28), C29(H29),
 C30(H30), C37(H37), C38(H38), C39(H39), C40(H40), C41(H41)
2.d Idealised Me refined as rotating group:
 C13(H13a,H13b,H13c), C21(H21a,H21b,H21c), C34(H34a,H34b,H34c), C42(H42a,H42b,
 H42c)
;
_shelx_res_checksum              76914
_shelx_hkl_checksum              15816
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on the spindle axis of 2 -1 2.'
_olex2_submission_special_instructions 'No special instructions were received'