Synthesis of indolizines from pyridinium 1,4-zwitterionic thiolates and α-functionalized bromoalkanes via a stepwise [(5+1)-1] pathway.
Cheng, Bin; Zhang, Xinping; Li, Yuntong; Li, Hui; He, Yixuan; Li, Yun; Wang, Taimin; Zhai, Hongbin; Chemical communications (Cambridge, England) 56 (2020) 8396–8399; doi:10.1039/d0cc03446k

data_7126684
_publ_section_title
;
 Synthesis of indolizines from pyridinium 1,4-zwitterionic thiolates and
 \a-functionalized bromoalkanes via a stepwise [(5+1)-1] pathway.
;
_journal_issue                   60
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              8396
_journal_page_last               8399
_journal_paper_doi               10.1039/d0cc03446k
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C25 H19 N O5 S'
_chemical_formula_sum            'C25 H19 N O5 S'
_chemical_formula_weight         445.47
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-12-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-12-07 deposited with the CCDC.	2020-06-12 downloaded from the CCDC.
;
_cell_angle_alpha                77.431(5)
_cell_angle_beta                 89.378(4)
_cell_angle_gamma                73.685(5)
_cell_formula_units_Z            2
_cell_length_a                   9.2626(5)
_cell_length_b                   10.0278(6)
_cell_length_c                   12.6230(7)
_cell_measurement_reflns_used    3224
_cell_measurement_temperature    293.63(13)
_cell_measurement_theta_max      70.0000
_cell_measurement_theta_min      10.2020
_cell_volume                     1096.71(11)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.63(13)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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     24.00  70.00   1.00    1.00    --    0.00  19.00   0.00   46
  2  \w     30.00 124.00   1.00    1.00    --   54.00  77.00 -30.00   94
  3  \w    106.00 175.00   1.00    1.00    --  108.00 111.00 -90.00   69
  4  \w    123.00 149.00   1.00    1.00    --  108.00 111.00-180.00   26
  5  \w    104.00 165.00   1.00    1.00    --  108.00 111.00-150.00   61
  6  \w    101.00 166.00   1.00    1.00    --  108.00 111.00-120.00   65
  7  \w     92.00 162.00   1.00    1.00    --  108.00  50.00-150.00   70
  8  \w     57.00 138.00   1.00    1.00    --  108.00 -77.00-150.00   81
  9  \w     83.00 116.00   1.00    1.00    --  108.00-111.00 -30.00   33
 10  \w     68.00 111.00   1.00    1.00    --  108.00-111.00-150.00   43
 11  \w     51.00 137.00   1.00    1.00    --  108.00 -25.00-180.00   86
 12  \w     46.00  72.00   1.00    1.00    --  108.00-111.00 -30.00   26
 13  \w     34.00 106.00   1.00    1.00    --   54.00-125.00 -60.00   72
 14  \w     39.00  64.00   1.00    1.00    --  108.00-111.00  90.00   25
 15  \w     72.00 110.00   1.00    1.00    --  108.00-111.00  90.00   38
 16  \w     42.00 130.00   1.00    1.00    --  108.00 -50.00 120.00   88
 17  \w     87.00 126.00   1.00    1.00    --  108.00  77.00 150.00   39
 18  \w    100.00 178.00   1.00    1.00    --  108.00 111.00 150.00   78
 19  \w    109.00 170.00   1.00    1.00    --  108.00 111.00 120.00   61
 20  \w     15.00 120.00   1.00    1.00    --   54.00  19.00 -60.00  105
 21  \w     24.00  68.00   1.00    1.00    --   54.00-125.00 120.00   44
 22  \w      7.00  72.00   1.00    1.00    --   54.00 -57.00   0.00   65
 23  \w    -12.00  65.00   1.00    1.00    --   54.00 -57.00 120.00   77
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1645332000
_diffrn_orient_matrix_UB_12      0.0464876000
_diffrn_orient_matrix_UB_13      -0.0455347000
_diffrn_orient_matrix_UB_21      -0.0013198000
_diffrn_orient_matrix_UB_22      -0.1570257000
_diffrn_orient_matrix_UB_23      0.0249555000
_diffrn_orient_matrix_UB_31      -0.0552140000
_diffrn_orient_matrix_UB_32      0.0125954000
_diffrn_orient_matrix_UB_33      0.1139518000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6851
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        66.600
_diffrn_reflns_theta_max         66.600
_diffrn_reflns_theta_min         4.982
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.627
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.349
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.580
_refine_diff_density_rms         0.088
_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     291
_refine_ls_number_reflns         3827
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0593
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0864P)^2^+0.4572P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1556
_refine_ls_wR_factor_ref         0.1637
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3319
_reflns_number_total             3827
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc03446k2.cif
_cod_data_source_block           zhangxp1_1204
_cod_depositor_comments          'Adding full bibliography for 7126684.cif.'
_cod_original_cell_volume        1096.70(11)
_cod_database_code               7126684
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_usercomment     'nature product'
_reflns_odcompleteness_completeness 99.28
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C10(H10), C13(H13), C14(H14), C16(H16), C17(H17), C18(H18), C19(H19),
 C23(H23), C24(H24), C26(H26), C27(H27), C28(H28), C29(H29)
2.b Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C31(H31A,H31B,H31C)
;
_shelx_res_checksum              81599
_shelx_hkl_checksum              49139
_olex2_date_sample_data_collection 2019-12-04
_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 1.833
_oxdiff_exptl_absorpt_empirical_full_min 0.726