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_4133659
_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         'C13 H18 N4 O3'
_chemical_formula_sum            'C13 H18 N4 O3'
_chemical_formula_weight         278.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-11-07
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.244(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.4136(10)
_cell_length_b                   6.0223(3)
_cell_length_c                   19.9058(8)
_cell_measurement_reflns_used    9877
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.15
_cell_measurement_theta_min      2.64
_cell_volume                     2679.5(2)
_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      99.95
_diffrn_detector                 'Bruker Photon 100 area detector'
_diffrn_detector_type            'photon counter area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            28276
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.186
_diffrn_reflns_theta_min         2.642
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8531
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1244 before and 0.0542 after correction. The Ratio of minimum to maximum transmission is 0.8531. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_description       tablet
_exptl_crystal_F_000             1184
_exptl_crystal_recrystallization_method
'Crystalization was done with slow diffusion in dichloromethane and diethy ether.'
_exptl_crystal_size_max          0.404
_exptl_crystal_size_mid          0.222
_exptl_crystal_size_min          0.128
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       0.0328(13)
_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   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         2980
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0376
_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^)+(0.0479P)^2^+2.8912P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.0969
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2765
_reflns_number_total             2980
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b13030_si_003.cif
_cod_data_source_block           mo_dd15k_0m
_cod_database_code               4133659
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.961
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H13A,H13B} of C13
 At 1.5 times of:
  All N(H) groups, {H9A,H9B} of C9
2.a Ternary CH refined with riding coordinates:
 C1(H1), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C5(H5), C6(H6)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_shelx_res_checksum              56577
_shelx_hkl_checksum              80252
_olex2_exptl_crystal_mounting_method
'the crystal was mounted on a loop with spindle axis of -1 -1 5.'
_olex2_submission_original_sample_id MO-V_424C_benzene_morpholine_Pd
_olex2_submission_special_instructions 'No special instructions were received'