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_4038170
_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_absolute_configuration ad
_chemical_formula_moiety         'C12 H18 N2 O4 S2'
_chemical_formula_sum            'C12 H18 N2 O4 S2'
_chemical_formula_weight         318.40
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-01-18
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.9470(3)
_cell_length_b                   14.4082(7)
_cell_length_c                   15.4652(7)
_cell_measurement_reflns_used    5681
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.6190
_cell_measurement_theta_min      4.0680
_cell_volume                     1547.97(12)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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    -88.00 -35.00   1.00    3.75    --  -15.76-178.00  90.00   53
  2  \w    -88.00 -35.00   1.00    3.75    --  -15.76-178.00-180.00   53
  3  \w    -51.00  44.00   1.00    3.75    --   17.01 -77.00  90.00   95
  4  \w    -83.00 -58.00   1.00    3.75    --  -15.76 -57.00  60.00   25
  5  \w      0.00  84.00   1.00    3.75    --   17.01  57.00  30.00   84
  6  \w    -10.00  85.00   1.00    3.75    --   17.01  77.00-180.00   95
;
_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      0.0578916000
_diffrn_orient_matrix_UB_12      -0.0166123000
_diffrn_orient_matrix_UB_13      0.0344947000
_diffrn_orient_matrix_UB_21      -0.0837005000
_diffrn_orient_matrix_UB_22      -0.0158543000
_diffrn_orient_matrix_UB_23      0.0217429000
_diffrn_orient_matrix_UB_31      0.0083972000
_diffrn_orient_matrix_UB_32      -0.0435023000
_diffrn_orient_matrix_UB_33      -0.0210604000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11897
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.51
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.357
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45064
_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    1.366
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.07(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2712
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0353
_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^)+(0.0409P)^2^+0.2727P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0813
_refine_ls_wR_factor_ref         0.0836
_reflns_number_gt                2498
_reflns_number_total             2712
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9b03305_si_004.cif
_cod_data_source_block           fp-22-1-2
_cod_original_cell_volume        1547.96(12)
_cod_database_code               4038170
_reflns_odcompleteness_completeness 99.46
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C8(H8), C9(H9), C11(H11), C13(H13)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,
 H18C)
;
_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 1.767
_oxdiff_exptl_absorpt_empirical_full_min 0.538