Palladium-catalyzed regioselective C-S bond cleavage of thiophenes.
Huang, Huanan; Li, Jing; Lescop, Christophe; Duan, Zheng; Organic letters 13 (2011) 5252–5255; doi:10.1021/ol2021302

data_1502486
_publ_section_title
;
 Palladium-catalyzed regioselective C-S bond cleavage of thiophenes.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              5252
_journal_page_last               5255
_journal_paper_doi               10.1021/ol2021302
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C H2 Cl2, C62 H50 S'
_chemical_formula_sum            'C63 H52 Cl2 S'
_chemical_formula_weight         912.01
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2011-05-06
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 96.848(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.8181(6)
_cell_length_b                   24.0094(12)
_cell_length_c                   15.1905(7)
_cell_measurement_reflns_used    4008
_cell_measurement_temperature    290.65
_cell_measurement_theta_max      72.4820
_cell_measurement_theta_min      3.2185
_cell_volume                     5003.7(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'A short history of SHELX (Sheldrick, 2007)'
_diffrn_ambient_temperature      290.65
_diffrn_detector_area_resol_mean 16.2312
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega   23.00   65.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   37.0000  -60.0000 42

  2 omega    8.00   34.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   37.0000 -180.0000 26

  3 omega  -17.00   10.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   37.0000  -60.0000 27

  4 omega -104.00  -27.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -50.0000 -180.0000 77

  5 omega  -95.00  -16.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  125.0000   60.0000 79

  6 omega  -39.00  -13.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000  -90.0000 26

  7 omega   27.00  121.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       55.8596   77.0000  -90.0000 94

  8 omega  -14.00   17.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       55.8596  -37.0000    0.0000 31

  9 omega   82.00  145.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      111.7191  -25.0000  -30.0000 63

 10 omega  109.00  135.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      111.7191  111.0000 -180.0000 26

 11 omega   83.00  146.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      111.7191  -25.0000 -120.0000 63

 12 omega  106.00  132.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      111.7191  -50.0000 -150.0000 26

 13 omega   85.00  176.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      111.7191  145.0000   69.0000 91

 14 omega  115.00  141.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      111.7191  -25.0000    0.0000 26

 15 omega   42.00  122.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      111.7191 -145.0000 -162.0000 80

 16 omega  119.00  171.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      111.7191  111.0000   30.0000 52

 17 omega   68.00   94.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      111.7191 -125.0000   98.0000 26

 18 omega   89.00  117.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      111.7191  -50.0000   90.0000 28

 19 omega   41.00   66.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      111.7191 -125.0000   98.0000 25

 20 omega   96.00  121.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      111.7191 -125.0000 -175.0000 25

 21 omega   69.00  126.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      111.7191 -145.0000  110.0000 57

 22 omega   88.00  125.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      111.7191  -50.0000   60.0000 37
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0282734000
_diffrn_orient_matrix_UB_12      0.0467752000
_diffrn_orient_matrix_UB_13      -0.0614372000
_diffrn_orient_matrix_UB_21      -0.0406481000
_diffrn_orient_matrix_UB_22      0.0437578000
_diffrn_orient_matrix_UB_23      0.0601353000
_diffrn_orient_matrix_UB_31      0.1007537000
_diffrn_orient_matrix_UB_32      0.0044808000
_diffrn_orient_matrix_UB_33      0.0550798000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_unetI/netI     0.0483
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20634
_diffrn_reflns_theta_full        67.08
_diffrn_reflns_theta_max         67.08
_diffrn_reflns_theta_min         3.46
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.850
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85030
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1920
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.651
_refine_diff_density_min         -0.716
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     601
_refine_ls_number_reflns         8931
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0950
_refine_ls_R_factor_gt           0.0658
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0933P)^2^+1.1637P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1748
_refine_ls_wR_factor_ref         0.1984
_reflns_number_gt                6064
_reflns_number_total             8931
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol2021302_si_002.cif
_cod_data_source_block           20110564
_cod_database_code               1502486
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97