Catalytic C-h and C-s bond activation of thiophenes.
Li, Jing; Huang, Huanan; Liang, Weihong; Gao, Qun; Duan, Zheng; Organic letters 15 (2013) 282–285; doi:10.1021/ol303136x

data_1508855
_publ_section_title
;
 Catalytic C-h and C-s bond activation of thiophenes.
;
_journal_issue                   2
_journal_name_full               'Organic letters'
_journal_page_first              282
_journal_page_last               285
_journal_paper_doi               10.1021/ol303136x
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C41 H28 F4 S, 0.5(C6 H14)'
_chemical_formula_sum            'C44 H35 F4 S'
_chemical_formula_weight         671.78
_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             2012-07-13
_audit_creation_method
;
  Olex2 1.2
  (compiled 2012.05.09 svn.r2324, GUI svn.r4230)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 92.4025(19)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.3242(2)
_cell_length_b                   20.5863(4)
_cell_length_c                   20.4716(4)
_cell_measurement_reflns_used    4975
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      66.9663
_cell_measurement_theta_min      4.2918
_cell_volume                     3926.09(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_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, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      291.15
_diffrn_detector_area_resol_mean 16.2312
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -60.00  -34.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000  -90.0000 26

  2 omega  -77.00  -52.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000  120.0000 25

  3 omega  -41.00   16.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   37.0000  -30.0000 57

  4 omega  -98.00  -25.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -61.0000  120.0000 73

  5 omega -112.00  -19.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -37.0000  -30.0000 93

  6 omega  -47.00   30.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   30.0000  -90.0000 77

  7 omega  -43.00  -15.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   30.0000 -120.0000 28

  8 omega   52.00   78.00   1.0000   47.0000
omega____ theta____ kappa____ phi______ frames
    -      111.7191  -94.0000 -180.0000 26

  9 omega   58.00   91.00   1.0000   47.0000
omega____ theta____ kappa____ phi______ frames
    -      111.7191  -30.0000 -180.0000 33

 10 omega   71.00   98.00   1.0000   47.0000
omega____ theta____ kappa____ phi______ frames
    -      111.7191  -45.0000 -150.0000 27

 11 omega   45.00  108.00   1.0000   47.0000
omega____ theta____ kappa____ phi______ frames
    -      111.7191  -94.0000  -90.0000 63

 12 omega   40.00   80.00   1.0000   47.0000
omega____ theta____ kappa____ phi______ frames
    -      111.7191  -30.0000  150.0000 40

 13 omega   44.00   89.00   1.0000   47.0000
omega____ theta____ kappa____ phi______ frames
    -      111.7191  -46.0000   84.0000 45

 14 omega   94.00  176.00   1.0000   47.0000
omega____ theta____ kappa____ phi______ frames
    -      111.7191   45.0000   30.0000 82

 15 omega   39.00   91.00   1.0000   47.0000
omega____ theta____ kappa____ phi______ frames
    -      111.7191  -30.0000  -90.0000 52

 16 omega   44.00  102.00   1.0000   47.0000
omega____ theta____ kappa____ phi______ frames
    -      111.7191  -61.0000  150.0000 58

 17 omega   76.00  122.00   1.0000   47.0000
omega____ theta____ kappa____ phi______ frames
    -      111.7191  -15.0000   60.0000 46

 18 omega  -26.00   72.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   37.0000   90.0000 98

 19 omega   30.00   78.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       55.8596   37.0000 -120.0000 48
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1205143000
_diffrn_orient_matrix_UB_12      0.0401998000
_diffrn_orient_matrix_UB_13      -0.0296797000
_diffrn_orient_matrix_UB_21      0.0990244000
_diffrn_orient_matrix_UB_22      -0.0147701000
_diffrn_orient_matrix_UB_23      0.0603351000
_diffrn_orient_matrix_UB_31      0.0551321000
_diffrn_orient_matrix_UB_32      -0.0613959000
_diffrn_orient_matrix_UB_33      -0.0339846000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            14449
_diffrn_reflns_theta_full        67.01
_diffrn_reflns_theta_max         67.01
_diffrn_reflns_theta_min         4.30
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_exptl_absorpt_coefficient_mu    1.115
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82605
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.137
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1404
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.781
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     473
_refine_ls_number_reflns         6991
_refine_ls_number_restraints     32
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0920
_refine_ls_R_factor_gt           0.0777
_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^)+(0.1742P)^2^+0.4153P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2294
_refine_ls_wR_factor_ref         0.2507
_reflns_number_gt                5386
_reflns_number_total             6991
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol303136x_si_002.cif
_cod_data_source_block           4c
_cod_original_cell_volume        3926.08(15)
_cod_database_code               1508855
_chemical_oxdiff_formula         'C11 H10 S O2'
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97