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_1502487
_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         'C52 H40 S'
_chemical_formula_sum            'C52 H40 S'
_chemical_formula_weight         696.90
_chemical_name_systematic
;
 ? 
;
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2011-06-23
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 111.199(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.2541(3)
_cell_length_b                   13.8703(2)
_cell_length_c                   19.9768(3)
_cell_measurement_reflns_used    4549
_cell_measurement_temperature    291.15
_cell_measurement_theta_max      71.8103
_cell_measurement_theta_min      3.1052
_cell_volume                     3940.65(12)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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      291.15
_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   27.00   53.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   37.0000   30.0000 26

  2 omega  -26.00   20.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   37.0000   30.0000 46

  3 omega  -47.00    9.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   25.0000    0.0000 56

  4 omega -110.00  -36.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -50.0000    0.0000 74

  5 omega  -38.00   25.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   25.0000  120.0000 63

  6 omega  -47.00    8.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   25.0000  -90.0000 55

  7 omega  -52.00  -25.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  108.0000  -56.0000 27

  8 omega  -13.00   26.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   37.0000 -180.0000 39

  9 omega   38.00   80.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0941  -25.0000  120.0000 42

 10 omega   69.00   94.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0941  -25.0000   60.0000 25

 11 omega   92.00  168.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0941   50.0000   60.0000 76

 12 omega   62.00   99.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0941  -76.0000  -57.0000 37

 13 omega  115.00  140.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0941  -76.0000  -57.0000 25

 14 omega   85.00  158.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0941   77.0000   90.0000 73

 15 omega   47.00   92.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0941  -50.0000 -120.0000 45

 16 omega  127.00  169.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0941   50.0000    0.0000 42

 17 omega   38.00   92.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0941  -25.0000  -90.0000 54

 18 omega   62.00  102.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0941  -50.0000  -60.0000 40

 19 omega   77.00  178.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0941   25.0000 -180.0000 101
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0403703000
_diffrn_orient_matrix_UB_12      -0.0925693000
_diffrn_orient_matrix_UB_13      0.0203336000
_diffrn_orient_matrix_UB_21      0.0702086000
_diffrn_orient_matrix_UB_22      0.0090570000
_diffrn_orient_matrix_UB_23      0.0777612000
_diffrn_orient_matrix_UB_31      -0.0719556000
_diffrn_orient_matrix_UB_32      0.0605884000
_diffrn_orient_matrix_UB_33      0.0195313000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            14712
_diffrn_reflns_theta_full        67.07
_diffrn_reflns_theta_max         67.07
_diffrn_reflns_theta_min         3.11
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.982
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94290
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     482
_refine_ls_number_reflns         7033
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0527
_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^)+(0.0809P)^2^+0.7206P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1512
_refine_ls_wR_factor_ref         0.1656
_reflns_number_gt                5350
_reflns_number_total             7033
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol2021302_si_002.cif
_cod_data_source_block           20110695
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_hydrogen_treatment' value 'CONSTR' changed to 'constr'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        3940.64(12)
_cod_database_code               1502487
_chemical_oxdiff_formula         'C11 H10 S O2'
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97