Direct C-H Arylation of Thiophenes at Low Catalyst Loading of a Phosphine-Free Bis(alkoxo)palladium Complex.
Li, Yabo; Wang, Jingran; Huang, Mengmeng; Wang, Zhiwei; Wu, Yusheng; Wu, Yangjie; The Journal of organic chemistry 79 (2014) 2890–2897; doi:10.1021/jo402745b

data_4029261
_publ_section_title
;
 Direct C-H Arylation of Thiophenes at Low Catalyst Loading of a
 Phosphine-Free Bis(alkoxo)palladium Complex.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2890
_journal_page_last               2897
_journal_paper_doi               10.1021/jo402745b
_journal_volume                  79
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H13 N S2, C H4 O'
_chemical_formula_sum            'C16 H17 N O S2'
_chemical_formula_weight         303.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-09-29
_audit_creation_method
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  Olex2 1.2
  (compiled 2012.05.09 svn.r2324, GUI svn.r4230)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.732(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   4.88121(19)
_cell_length_b                   15.8851(6)
_cell_length_c                   10.0737(4)
_cell_measurement_reflns_used    2353
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      25.1330
_cell_measurement_theta_min      3.2630
_cell_volume                     781.04(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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  -11.00   14.00   1.0000    1.1800
omega____ theta____ kappa____ phi______ frames
    -      -17.2885  -99.0000 -120.0000 25

  2 omega  -11.00   25.00   1.0000    1.1800
omega____ theta____ kappa____ phi______ frames
    -       19.8666  -57.0000 -120.0000 36

  3 omega   -6.00   80.00   1.0000    1.1800
omega____ theta____ kappa____ phi______ frames
    -       19.8666   37.0000 -150.0000 86

  4 omega   42.00   69.00   1.0000    1.1800
omega____ theta____ kappa____ phi______ frames
    -       19.7104  178.0000   60.0000 27

  5 omega   -4.00   36.00   1.0000    1.1800
omega____ theta____ kappa____ phi______ frames
    -       19.7104   37.0000  150.0000 40

  6 omega  -86.00    4.00   1.0000    1.1800
omega____ theta____ kappa____ phi______ frames
    -      -17.1323  -57.0000  -30.0000 90

  7 omega  -49.00   40.00   1.0000    1.1800
omega____ theta____ kappa____ phi______ frames
    -       19.7104  -57.0000   30.0000 89

  8 omega  -25.00   62.00   1.0000    1.1800
omega____ theta____ kappa____ phi______ frames
    -       19.7104  -99.0000 -120.0000 87

  9 omega   35.00   96.00   1.0000    1.1800
omega____ theta____ kappa____ phi______ frames
    -       19.7104  178.0000 -150.0000 61
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0179939000
_diffrn_orient_matrix_UB_12      0.0079103000
_diffrn_orient_matrix_UB_13      -0.0686160000
_diffrn_orient_matrix_UB_21      -0.0152434000
_diffrn_orient_matrix_UB_22      -0.0435809000
_diffrn_orient_matrix_UB_23      -0.0135127000
_diffrn_orient_matrix_UB_31      -0.1434532000
_diffrn_orient_matrix_UB_32      0.0056073000
_diffrn_orient_matrix_UB_33      -0.0080741000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7963
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.27
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.336
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98624
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         3118
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0389
_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^)+(0.0426P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0827
_refine_ls_wR_factor_ref         0.0891
_reflns_number_gt                2643
_reflns_number_total             3118
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo402745b_si_004.cif
_cod_data_source_block           201309155
_cod_depositor_comments
;Adding full bibliography for
 ./tmp-cod-update-bibliographies-12971/cifs/4029261.cif.
;
_cod_database_code               4029261
_chemical_oxdiff_formula         C1H1O1S2
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32