Synthesis of disulfides tethered pyrroles from β-ketothioamides via bicyclization/ring-opening/oxidative coupling reaction
Li, Cong-Xiang; Liu, Rui-Juan; Yin, Kun; Wen, Li-Rong; Li, Ming; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB00655A

data_7155697
_publ_section_title
;
 Synthesis of disulfides tethered pyrroles from \b-ketothioamides via
 bicyclization/ring-opening/oxidative coupling reaction
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB00655A
_journal_year                    2017
_chemical_formula_moiety         'C28 H19 F N2 O4 S'
_chemical_formula_sum            'C28 H19 F N2 O4 S'
_chemical_formula_weight         498.51
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/cc1k0kgl
_audit_creation_date             2015-10-09
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-10-09 deposited with the CCDC.
2017-06-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.036(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.382(5)
_cell_length_b                   12.608(3)
_cell_length_c                   10.333(3)
_cell_measurement_reflns_used    6720
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4800
_cell_measurement_theta_min      2.1557
_cell_volume                     2376.7(11)
_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 0.991
_diffrn_measured_fraction_theta_max 0.990
_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: 270.0000
                 XTD: 45.1096
              2theta: -19.8130
scan:
    Number of images: 282
               Slice: -80.0000 - 61.0000
         Image width: 0.5000
            Exp time: 10.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 180.0000
                 XTD: 45.1096
              2theta: -19.8130
;
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0231
_diffrn_orient_matrix_UB_12      0.0824
_diffrn_orient_matrix_UB_13      -0.0468
_diffrn_orient_matrix_UB_21      0.0211
_diffrn_orient_matrix_UB_22      0.0332
_diffrn_orient_matrix_UB_23      0.0689
_diffrn_orient_matrix_UB_31      0.0524
_diffrn_orient_matrix_UB_32      -0.0125
_diffrn_orient_matrix_UB_33      -0.0101
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16112
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.492
_diffrn_reflns_theta_min         2.756
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7754
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.168
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         5404
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.168
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0485
_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^)+(0.0200P)^2^+1.3176P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0899
_refine_ls_wR_factor_ref         0.0939
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4964
_reflns_number_total             5404
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob00655a2.cif
_cod_data_source_block           sa4373a
_cod_original_cell_volume        2376.8(10)
_cod_database_code               7155697
_shelxl_version_number           2013-4
_diffrn_number_total             5669
_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:
 C27(H27A,H27B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
2.c Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C)
;
_shelx_res_checksum              98980
_olex2_submission_special_instructions 'No special instructions were received'