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_1508856
_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         '2(C96 H76 S2), 3.5(C6)'
_chemical_formula_sum            'C213 H201 S4'
_chemical_formula_weight         2888.98
_chemical_name_systematic
;
 ? 
;
_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             2012-07-13
_audit_creation_method
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  Olex2 1.2
  (compiled 2012.05.09 svn.r2324, GUI svn.r4230)
;
_cell_angle_alpha                96.294(5)
_cell_angle_beta                 99.037(6)
_cell_angle_gamma                108.324(8)
_cell_formula_units_Z            1
_cell_length_a                   16.0668(17)
_cell_length_b                   16.7268(11)
_cell_length_c                   18.1635(8)
_cell_measurement_reflns_used    6521
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      63.5951
_cell_measurement_theta_min      2.9609
_cell_volume                     4510.0(7)
_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 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
  1 omega -111.00  -47.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -34.9673 -178.0000   90.0000 64

  2 omega -104.00  -14.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -34.9673  -57.0000 -120.0000 90

  3 omega  -54.00   34.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -34.9673   57.0000  120.0000 88

  4 omega  -72.00   38.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -34.9673   19.0000   60.0000 110

  5 omega   39.00   98.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       34.9673 -134.0000   61.0000 59

  6 omega   39.00   95.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      101.5359  -45.0000  -60.0000 56

  7 omega   30.00   86.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      101.5359  -30.0000  150.0000 56

  8 omega   34.00  123.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      101.5359  -61.0000  150.0000 89

  9 omega   29.00   88.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      101.5359  -30.0000 -120.0000 59

 10 omega   29.00  115.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      101.5359 -111.0000  -60.0000 86

 11 omega   33.00   99.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      101.5359  -45.0000    0.0000 66

 12 omega   59.00  150.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      101.5359  178.0000 -150.0000 91

 13 omega   30.00  108.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      101.5359  -94.0000  150.0000 78

 14 omega  106.00  169.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      101.5359   61.0000  -60.0000 63

 15 omega   32.00  130.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      101.5359  -77.0000  -60.0000 98

 16 omega   34.00  170.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      101.5359    0.0000   90.0000 136

 17 omega -104.00  -14.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -34.9673  -57.0000   90.0000 90

 18 omega -105.00   -5.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -34.9673  -77.0000    0.0000 100

 19 omega -105.00   -5.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -34.9673  -77.0000 -180.0000 100

 20 omega   57.00  111.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       34.9673  178.0000   30.0000 54
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0997348000
_diffrn_orient_matrix_UB_12      0.0090383000
_diffrn_orient_matrix_UB_13      0.0084510000
_diffrn_orient_matrix_UB_21      -0.0112117000
_diffrn_orient_matrix_UB_22      -0.0151204000
_diffrn_orient_matrix_UB_23      -0.0867362000
_diffrn_orient_matrix_UB_31      0.0244957000
_diffrn_orient_matrix_UB_32      0.0969867000
_diffrn_orient_matrix_UB_33      0.0006715000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_unetI/netI     0.0426
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            29186
_diffrn_reflns_theta_full        63.67
_diffrn_reflns_theta_max         63.67
_diffrn_reflns_theta_min         2.96
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.868
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78724
_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    1.064
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1543
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.529
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     997
_refine_ls_number_reflns         14744
_refine_ls_number_restraints     62
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.1133
_refine_ls_R_factor_gt           0.0741
_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^)+(0.1296P)^2^+0.4194P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2022
_refine_ls_wR_factor_ref         0.2454
_reflns_number_gt                9060
_reflns_number_total             14744
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol303136x_si_002.cif
_cod_data_source_block           6a
_cod_original_cell_volume        4510.0(6)
_cod_database_code               1508856
_chemical_oxdiff_formula         'C11 H10 S O2'
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     63.60