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_1508853
_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         'C52 H30 F6 S'
_chemical_formula_sum            'C52 H30 F6 S'
_chemical_formula_weight         800.82
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-05-11
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.06 svn.r2239, GUI svn.r4109)
;
_cell_angle_alpha                85.320(4)
_cell_angle_beta                 82.624(4)
_cell_angle_gamma                72.927(4)
_cell_formula_units_Z            2
_cell_length_a                   11.2017(6)
_cell_length_b                   12.1697(6)
_cell_length_c                   15.1195(7)
_cell_measurement_reflns_used    6440
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      66.9640
_cell_measurement_theta_min      3.8004
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_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega   -4.00   21.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000   60.0000 25

  2 omega   37.00   63.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -180.0000 26

  3 omega  -49.00    6.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   37.0000  -60.0000 55

  4 omega -106.00  -45.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  178.0000   60.0000 61

  5 omega  -73.00   28.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   77.0000   90.0000 101

  6 omega  -46.00   13.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   30.0000    0.0000 59

  7 omega  -21.00   15.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   61.0000    0.0000 36

  8 omega -118.00  -83.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  178.0000 -150.0000 35

  9 omega -112.00  -53.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -37.0000   30.0000 59

 10 omega  -22.00   30.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   30.0000 -150.0000 52

 11 omega   30.00  102.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       55.8625 -125.0000  -90.0000 72

 12 omega   51.00  103.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      111.7251  -94.0000 -120.0000 52

 13 omega   49.00   99.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      111.7251  -45.0000 -150.0000 50

 14 omega   63.00  109.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      111.7251  -94.0000   60.0000 46

 15 omega   41.00   99.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      111.7251  -45.0000   90.0000 58

 16 omega   46.00   72.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      111.7251  -30.0000  -30.0000 26

 17 omega   55.00  109.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      111.7251  -94.0000  -30.0000 54

 18 omega   82.00  127.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      111.7251  -61.0000  -60.0000 45

 19 omega   42.00   68.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      111.7251  -30.0000 -180.0000 26

 20 omega  120.00  178.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      111.7251   30.0000 -150.0000 58

 21 omega   42.00   90.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      111.7251  -45.0000  150.0000 48

 22 omega   67.00  115.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      111.7251 -111.0000 -120.0000 48

 23 omega   56.00   81.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      111.7251  -30.0000  -60.0000 25

 24 omega   41.00   99.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      111.7251  -45.0000   30.0000 58

 25 omega   41.00   98.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      111.7251  -45.0000  -90.0000 57

 26 omega   56.00   82.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      111.7251  -30.0000   30.0000 26

 27 omega   39.00  102.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      111.7251 -111.0000 -180.0000 63

 28 omega   43.00  177.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      111.7251    0.0000 -180.0000 134

 29 omega  -70.00   30.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -77.0000 -120.0000 100

 30 omega -111.00  -21.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -57.0000  -60.0000 90

 31 omega -111.00  -21.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -57.0000   90.0000 90

 32 omega -112.00  -15.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -73.0000 -159.0000 97
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1391763000
_diffrn_orient_matrix_UB_12      0.0647612000
_diffrn_orient_matrix_UB_13      -0.0073925000
_diffrn_orient_matrix_UB_21      -0.0385813000
_diffrn_orient_matrix_UB_22      -0.0683669000
_diffrn_orient_matrix_UB_23      0.0835098000
_diffrn_orient_matrix_UB_31      0.0094392000
_diffrn_orient_matrix_UB_32      0.0933000000
_diffrn_orient_matrix_UB_33      0.0595712000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14087
_diffrn_reflns_theta_full        67.08
_diffrn_reflns_theta_max         67.08
_diffrn_reflns_theta_min         3.80
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_exptl_absorpt_coefficient_mu    1.296
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78005
_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    1.363
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.34
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     532
_refine_ls_number_reflns         6973
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0508
_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
'calc w=1/[\s^2^(Fo^2^)+(0.0680P)^2^+0.3293P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1181
_refine_ls_wR_factor_ref         0.1253
_reflns_number_gt                5912
_reflns_number_total             6973
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol303136x_si_002.cif
_cod_data_source_block           3ad
_cod_original_cell_volume        1951.88(16)
_cod_database_code               1508853
_chemical_oxdiff_formula         'C11 H10 S O2'
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97