Pd(II)-Catalyzed Aerobic Intermolecular 1,2-Diamination of Conjugated Dienes: A Regio- and Chemoselective [4 + 2] Annulation for the Synthesis of Tetrahydroquinoxalines.
Wu, Zhengxing; Wen, Ke; Zhang, Jingang; Zhang, Wanbin; Organic letters 19 (2017) 2813–2816; doi:10.1021/acs.orglett.7b00919

data_1546032
_publ_section_title
;
 Pd(II)-Catalyzed Aerobic Intermolecular 1,2-Diamination of Conjugated
 Dienes: A Regio- and Chemoselective [4 + 2] Annulation for the Synthesis
 of Tetrahydroquinoxalines.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2813
_journal_page_last               2816
_journal_paper_doi               10.1021/acs.orglett.7b00919
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C26 H26 N2 O4 S2'
_chemical_formula_sum            'C26 H26 N2 O4 S2'
_chemical_formula_weight         494.61
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-11-07
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 101.189(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.7471(7)
_cell_length_b                   12.3553(6)
_cell_length_c                   15.5929(11)
_cell_measurement_reflns_used    2221
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.4758
_cell_measurement_theta_min      3.2517
_cell_volume                     2409.1(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0117261000
_diffrn_orient_matrix_UB_12      -0.0034981000
_diffrn_orient_matrix_UB_13      -0.0462818000
_diffrn_orient_matrix_UB_21      -0.0149759000
_diffrn_orient_matrix_UB_22      -0.0549498000
_diffrn_orient_matrix_UB_23      0.0028972000
_diffrn_orient_matrix_UB_31      -0.0534492000
_diffrn_orient_matrix_UB_32      0.0162057000
_diffrn_orient_matrix_UB_33      -0.0002180000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9269
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.26
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.257
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95571
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.36
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         4400
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0472
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0475P)^2^+0.9425P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1086
_refine_ls_wR_factor_ref         0.1246
_reflns_number_gt                3184
_reflns_number_total             4400
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol7b00919_si_002.cif
_cod_data_source_block           141107_wzx141106_sample2
_cod_depositor_comments
'Adding full bibliography for 1546032--1546033.cif.'
_cod_original_cell_volume        2409.1(2)
_cod_database_code               1546032
_chemical_oxdiff_formula         'c10 h10 n2 o8 S1'
_reflns_odcompleteness_completeness 99.56
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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
2.a Ternary CH refined with riding coordinates:
 C7(H7), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C14(H14), C15(H15),
 C17(H17), C18(H18), C21(H21), C22(H22), C24(H24), C25(H25)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C26(H26A,H26B,H26C)
;