Palladium-Catalyzed Dearomative syn-1,4-Carboamination.
Okumura, Mikiko; Shved, Alexander S.; Sarlah, David; Journal of the American Chemical Society  (2017) –; doi:10.1021/jacs.7b11663

data_4126802
_publ_section_title
;
 Palladium-Catalyzed Dearomative syn-1,4-Carboamination.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.7b11663
_journal_year                    2017
_chemical_formula_moiety         'C21 H25 N3 O3, 0.5(C H2 Cl2)'
_chemical_formula_sum            'C21.5 H26 Cl N3 O3'
_chemical_formula_weight         409.90
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2017-10-25
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                90
_cell_angle_beta                 110.1730(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.3397(5)
_cell_length_b                   10.4840(2)
_cell_length_c                   17.3377(4)
_cell_measurement_reflns_used    13589
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.33
_cell_measurement_theta_min      2.50
_cell_volume                     3982.17(15)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker Photon 100 area detector'
_diffrn_detector_type            'photon counter area detector'
_diffrn_measured_fraction_theta_full 1.000
_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  0.0684
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_Laue_measured_fraction_full 1.000
_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       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            53785
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.392
_diffrn_reflns_theta_min         2.311
_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    0.221
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6884
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1121 before and 0.0618 after correction. The Ratio of minimum to maximum transmission is 0.9238. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_description       prism
_exptl_crystal_F_000             1736
_exptl_crystal_recrystallization_method
'recrystalized from diethyl ether and hexane co-solvent'
_exptl_crystal_size_max          0.316
_exptl_crystal_size_mid          0.213
_exptl_crystal_size_min          0.082
_refine_diff_density_max         0.857
_refine_diff_density_min         -0.552
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     522
_refine_ls_number_reflns         7329
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0453
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0568P)^2^+3.0182P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1063
_refine_ls_wR_factor_ref         0.1186
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5608
_reflns_number_total             7329
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b11663_si_006.cif
_cod_data_source_block           mo_dd36j2_xprep
_cod_depositor_comments
;

2020-07-21
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C21 H25 N3 O3), C H2 Cl2'
_cod_original_formula_sum        'C43 H52 Cl2 N6 O6'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     819.80
_cod_database_code               4126802
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.934
_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), C15(H15), C22(H22), C25(H25), C36(H36)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,
 H20B), C21(H21A,H21B), C37(H37A,H37B), C38(H38A,H38B), C39(H39A,H39B),
 C40(H40A,H40B), C41(H41A,H41B), C42(H42A,H42B), C43(H43A,H43B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C6(H6), C7(H7), C8(H8), C9(H9), C23(H23), C24(H24), C27(H27),
  C28(H28), C29(H29), C30(H30)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C34(H34A,H34B,H34C)
;
_shelx_res_checksum              70008
_shelx_hkl_checksum              62208
_olex2_exptl_crystal_mounting_method
'the crystal was mounted on a loop with spindle axis of 1 1 4.'
_olex2_submission_original_sample_id naphthalene_cyclooctanone_racemic
_olex2_submission_special_instructions 'No special instructions were received'