Synthesis of pyrrole disulfides via umpolung of β-ketothioamides
Meng, Xiangrui; Guo, Weisi; Nan, Guang-Ming; Li, Ming; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB01506D

data_7158887
_publ_section_title
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 Synthesis of pyrrole disulfides via umpolung of \b-ketothioamides
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_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01506D
_journal_year                    2022
_chemical_formula_moiety         'C40 H34 N4 O6 S2, C H2 Cl2'
_chemical_formula_sum            'C41 H36 Cl2 N4 O6 S2'
_chemical_formula_weight         815.76
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2015-12-02
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2018-04-18 deposited with the CCDC.	2022-09-20 downloaded from the CCDC.
;
_cell_angle_alpha                102.494(7)
_cell_angle_beta                 94.881(5)
_cell_angle_gamma                91.629(5)
_cell_formula_units_Z            2
_cell_length_a                   8.200(3)
_cell_length_b                   14.629(5)
_cell_length_c                   17.002(6)
_cell_measurement_reflns_used    6790
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4830
_cell_measurement_theta_min      1.2321
_cell_volume                     1981.7(12)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution
;
'SHELXT (Sheldrick, 2014)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 39.9565
	          2theta: -19.8344
scan:
	Number of images: 264
	           Slice: -77.0000 - 55.0000
	     Image width: 0.5000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 39.9565
	          2theta: -19.8344
scan:
	Number of images: 240
	           Slice: -110.0000 - 10.0000
	     Image width: 0.5000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 270.0000
	             XTD: 39.9565
	          2theta: -19.8344
;
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0870
_diffrn_orient_matrix_UB_12      0.0454
_diffrn_orient_matrix_UB_13      -0.0734
_diffrn_orient_matrix_UB_21      0.0024
_diffrn_orient_matrix_UB_22      0.0608
_diffrn_orient_matrix_UB_23      0.0348
_diffrn_orient_matrix_UB_31      0.0454
_diffrn_orient_matrix_UB_32      -0.0088
_diffrn_orient_matrix_UB_33      0.0390
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0687
_diffrn_reflns_av_unetI/netI     0.0723
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            21520
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_min         1.427
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.322
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6608
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_description       rod
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.596
_exptl_crystal_size_mid          0.066
_exptl_crystal_size_min          0.035
_refine_diff_density_max         0.929
_refine_diff_density_min         -0.500
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     533
_refine_ls_number_reflns         8909
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.115
_refine_ls_R_factor_all          0.0960
_refine_ls_R_factor_gt           0.0772
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0551P)^2^+1.9572P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1684
_refine_ls_wR_factor_ref         0.1797
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7251
_reflns_number_total             8909
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01506d2.cif
_cod_data_source_block           mx4339
_cod_original_cell_volume        1981.8(11)
_cod_database_code               7158887
_diffrn_number_total             8910
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(H41C)=Sof(H41D)=Sof(Cl2A)=Sof(Cl1A)=1-FVAR(1)
 Sof(Cl1)=Sof(Cl2)=Sof(H41A)=Sof(H41B)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C33(H33A,H33B), C41(H41A,H41B), C41(H41C,H41D)
3.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20), C27(H27), C28(H28), C29(H29), C30(H30), C31(H31), C36(H36),
  C37(H37), C38(H38), C39(H39), C40(H40)
3.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C34(H34A,H34B,H34C)
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_shelx_res_checksum              1033
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'