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_1508854
_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         'C69 H52 S'
_chemical_formula_sum            'C69 H52 S'
_chemical_formula_weight         913.17
_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             2012-04-11
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_cell_angle_alpha                70.764(7)
_cell_angle_beta                 77.704(6)
_cell_angle_gamma                82.037(7)
_cell_formula_units_Z            2
_cell_length_a                   10.4792(8)
_cell_length_b                   13.4657(11)
_cell_length_c                   20.0797(14)
_cell_measurement_reflns_used    4142
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      66.9639
_cell_measurement_theta_min      3.4811
_cell_volume                     2606.7(4)
_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  -74.00  -45.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000  -90.0000 29

  2 omega  -36.00   24.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   19.0000  -30.0000 60

  3 omega  -85.00  -10.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -37.0000  120.0000 75

  4 omega  -75.00  -40.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   19.0000  -30.0000 35

  5 omega    8.00   74.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000 -180.0000 66

  6 omega   21.00   46.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   83.0000  -82.0000 25

  7 omega   28.00  117.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000  150.0000 89

  8 omega  -15.00   68.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000  -60.0000 83

  9 omega   11.00  120.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   19.0000  120.0000 109

 10 omega   36.00  103.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000  120.0000 67

 11 omega   47.00  134.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   30.0000 87

 12 omega   35.00   92.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -90.0000 57

 13 omega   36.00   83.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -37.0000   30.0000 47

 14 omega   38.00   64.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   60.0000 26

 15 omega   62.00   93.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   30.0000 31

 16 omega  128.00  162.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   12.0000  120.0000 34

 17 omega   37.00  116.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -120.0000 79

 18 omega   38.00   64.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -37.0000 -180.0000 26

 19 omega   86.00  150.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000  -90.0000 64

 20 omega   92.00  118.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   12.0000  120.0000 26

 21 omega   50.00   94.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -150.0000 44

 22 omega   35.00   83.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   90.0000 48

 23 omega   40.00   91.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -37.0000  120.0000 51

 24 omega   59.00   85.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000  150.0000 26

 25 omega   37.00   84.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -91.0000 -120.0000 47

 26 omega   97.00  144.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -91.0000 -120.0000 47

 27 omega  107.00  143.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000  -60.0000 36

 28 omega   36.00   73.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -37.0000 -150.0000 37

 29 omega  119.00  175.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   25.0000    0.0000 56

 30 omega   58.00   98.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000  150.0000 40

 31 omega   75.00  111.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   60.0000 36

 32 omega   43.00  115.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000 -120.0000 72

 33 omega   87.00  163.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000 -120.0000 76

 34 omega  153.00  178.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 25

 35 omega   41.00   75.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   12.0000  120.0000 34
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0616195000
_diffrn_orient_matrix_UB_12      0.1062660000
_diffrn_orient_matrix_UB_13      -0.0372809000
_diffrn_orient_matrix_UB_21      0.0758126000
_diffrn_orient_matrix_UB_22      -0.0417227000
_diffrn_orient_matrix_UB_23      -0.0612265000
_diffrn_orient_matrix_UB_31      -0.1148890000
_diffrn_orient_matrix_UB_32      0.0414061000
_diffrn_orient_matrix_UB_33      -0.0410753000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_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            20713
_diffrn_reflns_theta_full        67.19
_diffrn_reflns_theta_max         67.19
_diffrn_reflns_theta_min         3.49
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_exptl_absorpt_coefficient_mu    0.860
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77793
_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    1.163
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             964
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.00067(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     635
_refine_ls_number_reflns         9306
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0523
_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^)+(0.0715P)^2^+0.2093P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1359
_refine_ls_wR_factor_ref         0.1573
_reflns_number_gt                6432
_reflns_number_total             9306
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol303136x_si_002.cif
_cod_data_source_block           5a
_cod_original_cell_volume        2606.7(3)
_cod_database_code               1508854
_chemical_oxdiff_formula         'C11 H10 S O2'
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97