Acid-catalyzed regioselective remote heteroarylation of alkenes via CC bond migration
Qin, Shengxiang; Zhang, Yaqi; Jiang, Long; Tse, Man Kin; Chan, Albert S. C.; Qiu, Liqin; Green Chemistry 26 (2024) 10299–10307; doi:10.1039/D4GC03356F

data_7249253
_publ_section_title
;
 Acid-catalyzed regioselective remote heteroarylation of alkenes via
 C&#xE001;C bond migration
;
_journal_issue                   19
_journal_name_full               'Green Chemistry'
_journal_page_first              10299
_journal_page_last               10307
_journal_paper_doi               10.1039/D4GC03356F
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C17 H14 S'
_chemical_formula_sum            'C17 H14 S'
_chemical_formula_weight         250.34
_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     dual
_audit_creation_date             2021-06-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-11-15 deposited with the CCDC.	2024-08-26 downloaded from the CCDC.
;
_cell_angle_alpha                105.060(9)
_cell_angle_beta                 106.146(9)
_cell_angle_gamma                103.841(10)
_cell_formula_units_Z            2
_cell_length_a                   8.2038(9)
_cell_length_b                   8.2643(9)
_cell_length_c                   10.5638(10)
_cell_measurement_reflns_used    1608
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      72.4410
_cell_measurement_theta_min      4.6180
_cell_volume                     625.76(13)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.951
_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   -110.00 -16.00   1.00    1.00    --  -40.77 -57.00 120.00   94
  2  \w    -63.00  28.00   1.00    1.00    --  -40.77  57.00 -90.00   91
  3  \w     57.00  99.00   1.00    1.00    --   40.77-133.00  90.00   42
  4  \w    -32.00  63.00   1.00    1.00    --   40.77 -38.00 -30.00   95
  5  \w     89.00 170.00   1.00    1.02    --  105.29  45.00  30.00   81
  6  \w     27.00  97.00   1.00    1.02    --  105.29 -94.00  60.00   70
  7  \w     36.00  91.00   1.00    1.02    --  105.29 -45.00  30.00   55
  8  \w     38.00  81.00   1.00    1.02    --  105.29-125.00   0.00   43
  9  \w     77.00 123.00   1.00    1.02    --  105.29  30.00-150.00   46
 10  \w     82.00 112.00   1.00    1.02    --  105.29-125.00   0.00   30
 11  \w     29.00  71.00   1.00    1.02    --  105.29 -94.00-180.00   42
 12  \w     83.00 109.00   1.00    1.02    --  105.29-125.00 -90.00   26
 13  \w     42.00 112.00   1.00    1.02    --  105.29-125.00-180.00   70
 14  \w     82.00 177.00   1.00    1.02    --  105.29  30.00 -60.00   95
 15  \w     35.00 124.00   1.00    1.02    --  105.29 -61.00-180.00   89
 16  \w    126.00 153.00   1.00    1.02    --  105.29  77.00-150.00   27
 17  \w     97.00 166.00   1.00    1.02    --  105.29 125.00 120.00   69
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0657536000
_diffrn_orient_matrix_UB_12      -0.1055590000
_diffrn_orient_matrix_UB_13      0.0921117000
_diffrn_orient_matrix_UB_21      -0.0431029000
_diffrn_orient_matrix_UB_22      -0.1589295000
_diffrn_orient_matrix_UB_23      -0.1333326000
_diffrn_orient_matrix_UB_31      0.1920804000
_diffrn_orient_matrix_UB_32      0.0748356000
_diffrn_orient_matrix_UB_33      0.0020920000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3942
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.014
_diffrn_reflns_theta_min         4.652
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_description       block
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2387
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.986
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0436
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1285
_refine_ls_wR_factor_ref         0.1400
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2101
_reflns_number_total             2387
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4gc03356f2.cif
_cod_data_source_block           a21060801aqlq1
_cod_depositor_comments          'Adding full bibliography for 7249253.cif.'
_cod_original_cell_volume        625.75(12)
_cod_database_code               7249253
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         CHS
_chemical_oxdiff_usercomment     210608
_reflns_odcompleteness_completeness 99.33
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17)
;
_olex2_date_sample_data_collection 2021-06-08
_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 1.361
_oxdiff_exptl_absorpt_empirical_full_min 0.721