Access to (Z)-1,2-Endiamides and 1,1-Endiamides via a Base-Promoted Tandem Reaction.
Zhang, Zhenming; Fu, Bei; Wang, Hui; Chen, Han; Tu, Yongliang; Zhao, Junfeng; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.9b03305

data_4038169
_publ_section_title
;
 Access to (Z)-1,2-Endiamides and 1,1-Endiamides via a Base-Promoted
 Tandem Reaction.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03305
_journal_year                    2020
_chemical_formula_moiety         'C20 H24 N2 O4 S2'
_chemical_formula_sum            'C20 H24 N2 O4 S2'
_chemical_formula_weight         420.53
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-11-10
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 115.121(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.2491(10)
_cell_length_b                   7.7250(3)
_cell_length_c                   16.6517(10)
_cell_measurement_reflns_used    5901
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.8920
_cell_measurement_theta_min      3.9070
_cell_volume                     2009.0(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.37b (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.37b (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.37b (Rigaku OD, 2017)'
_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    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0353
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -83.00  11.00   1.00    3.06    --  -15.92 -77.00 150.00   94
  2  \w     34.00  90.00   1.00    3.06    --   17.01-178.00 120.00   56
  3  \w     34.00  90.00   1.00    3.06    --   17.01-178.00 -90.00   56
  4  \w      0.00  84.00   1.00    3.06    --   17.01  57.00  90.00   84
  5  \w    -10.00  85.00   1.00    3.06    --   17.01  77.00 -60.00   95
  6  \w    -88.00 -51.00   1.00    3.06    --  -15.92-178.00-180.00   37
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0316412000
_diffrn_orient_matrix_UB_12      -0.0446182000
_diffrn_orient_matrix_UB_13      -0.0085670000
_diffrn_orient_matrix_UB_21      -0.0301914000
_diffrn_orient_matrix_UB_22      -0.0655141000
_diffrn_orient_matrix_UB_23      -0.0226398000
_diffrn_orient_matrix_UB_31      -0.0122565000
_diffrn_orient_matrix_UB_32      0.0462687000
_diffrn_orient_matrix_UB_33      -0.0403567000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16279
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.46
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.294
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37822
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.37b (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.496
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3956
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0457
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0458P)^2^+0.9550P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1067
_refine_ls_wR_factor_ref         0.1131
_reflns_number_gt                3336
_reflns_number_total             3956
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9b03305_si_003.cif
_cod_data_source_block           225-2
_cod_original_cell_volume        2008.96(19)
_cod_database_code               4038169
_reflns_odcompleteness_completeness 99.68
_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 Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C22(H22A,H22B), C23(H23A,H23B), C28(H28A,H28B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C10(H10), C12(H12), C16(H16), C17(H17), C18(H18), C20(H20), C24(H24),
 C25(H25), C27(H27)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C21(H21A,H21B,H21C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.943
_oxdiff_exptl_absorpt_empirical_full_min 0.493