Iodine-mediated decarboxylative coupling to synthesize β-sulfonyl-ene-amines/2,3-diarythio-pyrroles from α-amino acids and sodium sulfinates.
Yang, Xiaodong; Yang, Feng; Zhang, Xiaoya; Organic & biomolecular chemistry 22 (2024) 7321–7326; doi:10.1039/d4ob01149j

data_7160102
_publ_section_title
;
 Iodine-mediated decarboxylative coupling to synthesize
 &#x3b2;-sulfonyl-ene-amines/2,3-diarythio-pyrroles from &#x3b1;-amino
 acids and sodium sulfinates.
;
_journal_issue                   36
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7321
_journal_page_last               7326
_journal_paper_doi               10.1039/d4ob01149j
_journal_volume                  22
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H19 N O2 S'
_chemical_formula_sum            'C18 H19 N O2 S'
_chemical_formula_weight         313.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/ccdc.csd.cc1zvds0
_audit_creation_date             2016-04-08
_audit_creation_method
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Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
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_audit_update_record
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2018-05-11 deposited with the CCDC.	2024-08-19 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 115.357(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.0792(9)
_cell_length_b                   7.9190(4)
_cell_length_c                   11.2172(10)
_cell_measurement_reflns_used    842
_cell_measurement_temperature    290.83(10)
_cell_measurement_theta_max      24.5950
_cell_measurement_theta_min      4.0190
_cell_volume                     809.07(13)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
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_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega   20.00   74.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854   57.0000   60.0000 27

  2 omega   -8.00   24.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479  -99.0000    0.0000 16

  3 omega  -46.00   38.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -38.0000 -120.0000 42

  4 omega   34.00   88.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854   57.0000 -180.0000 27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
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_diffrn_orient_matrix_UB_11      0.0764875000
_diffrn_orient_matrix_UB_12      0.0161541000
_diffrn_orient_matrix_UB_13      0.0302498000
_diffrn_orient_matrix_UB_21      -0.0040408000
_diffrn_orient_matrix_UB_22      0.0194801000
_diffrn_orient_matrix_UB_23      0.0601501000
_diffrn_orient_matrix_UB_31      0.0134619000
_diffrn_orient_matrix_UB_32      -0.0859443000
_diffrn_orient_matrix_UB_33      0.0192924000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_unetI/netI     0.0610
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3222
_diffrn_reflns_theta_full        26.01
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         3.41
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87633
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.258
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_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.07(11)
_refine_ls_extinction_method     none
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_refine_ls_number_parameters     200
_refine_ls_number_reflns         2566
_refine_ls_number_restraints     1
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_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0497
_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^)+(0.0348P)^2^+0.0695P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.1104
_reflns_number_gt                2088
_reflns_number_total             2566
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d4ob01149j2.cif
_cod_data_source_block           yanrl_0405
_cod_depositor_comments          'Adding full bibliography for 7160102.cif.'
_cod_original_cell_volume        809.07(11)
_cod_database_code               7160102
_reflns_odcompleteness_completeness 99.55
_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:
 C8(H8A,H8B), C9(H9A,H9B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C10(H10), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_olex2_date_sample_data_collection 2016-04-05
_olex2_submission_special_instructions 'No special instructions were received'