Palladium-catalyzed C‒S bond activation and functionalization of 3-sulfenylindoles and related electron-rich heteroarenes
Li, Jianxiao; An, Yanni; Li, Jiawei; Yang, Shaorong; Wu, Wanqing; Jiang, Huanfeng; Organic Chemistry Frontiers 4 (2017) 1590–; doi:10.1039/C7QO00215G

data_1553770
_publ_section_title
;
 Palladium-catalyzed C--S bond activation and functionalization of
 3-sulfenylindoles and related electron-rich heteroarenes
;
_journal_issue                   8
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1590
_journal_paper_doi               10.1039/C7QO00215G
_journal_volume                  4
_journal_year                    2017
_chemical_formula_moiety         'C20 H12 Cl3 N'
_chemical_formula_sum            'C20 H12 Cl3 N O0'
_chemical_formula_weight         372.66
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-10-18
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_audit_update_record
;
2016-12-27 deposited with the CCDC.
2017-05-10 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 94.7142(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.93574(15)
_cell_length_b                   7.18231(8)
_cell_length_c                   19.3705(2)
_cell_measurement_reflns_used    4373
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      74.0500
_cell_measurement_theta_min      3.7160
_cell_volume                     1654.94(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_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    -64.00  21.00   1.00    1.00    --  -41.89  37.00 -60.00   85
  2  \w    -70.00  27.00   1.00    1.00    --  -41.89  57.00  30.00   97
  3  \w     51.00  92.00   1.00    1.00    --   41.89-125.00-180.00   41
  4  \w     36.00 134.00   1.00    1.00    --  107.79 -61.00-150.00   98
  5  \w     88.00 114.00   1.00    1.00    --  107.79  45.00   0.00   26
  6  \w    136.00 177.00   1.00    1.00    --  107.79  45.00   0.00   41
  7  \w    110.00 177.00   1.00    1.00    --  107.79 125.00-120.00   67
  8  \w    103.00 150.00   1.00    1.00    --  107.79 125.00-150.00   47
  9  \w     89.00 121.00   1.00    1.00    --  107.79  30.00  30.00   32
 10  \w     58.00  83.00   1.00    1.00    --  107.79 -98.00 -14.00   25
 11  \w     26.00  91.00   1.00    1.00    --  107.79 -94.00-180.00   65
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0793921000
_diffrn_orient_matrix_UB_12      -0.0026549000
_diffrn_orient_matrix_UB_13      0.0587945000
_diffrn_orient_matrix_UB_21      0.0878711000
_diffrn_orient_matrix_UB_22      0.1078227000
_diffrn_orient_matrix_UB_23      0.0469837000
_diffrn_orient_matrix_UB_31      -0.0523164000
_diffrn_orient_matrix_UB_32      0.1855238000
_diffrn_orient_matrix_UB_33      -0.0264937000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            5976
_diffrn_reflns_theta_full        74.00
_diffrn_reflns_theta_max         74.00
_diffrn_reflns_theta_min         4.20
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.003
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54767
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
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    1.496
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.513
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3260
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0398
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0696P)^2^+0.5226P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1081
_refine_ls_wR_factor_ref         0.1101
_reflns_number_gt                3084
_reflns_number_total             3260
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7qo00215g2.cif
_cod_data_source_block           1609263
_cod_database_code               1553770
_chemical_oxdiff_formula         'C20 H20 N4 O4'
_chemical_oxdiff_usercomment     CL-55
_reflns_odcompleteness_completeness 99.94
_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 N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N4(H4), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13),
 C16(H16), C18(H18), C20(H20), C22(H22)
;
_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 1.648
_oxdiff_exptl_absorpt_empirical_full_min 0.662