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_4029259
_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         'C16 H13 N S'
_chemical_formula_sum            'C16 H13 N S'
_chemical_formula_weight         251.33
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-09-06
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.5783(13)
_cell_length_b                   10.3365(6)
_cell_length_c                   5.9411(2)
_cell_measurement_reflns_used    1873
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      71.7820
_cell_measurement_theta_min      4.7220
_cell_volume                     1325.13(12)
_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 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
  1 omega  -25.00    1.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   37.0000 -150.0000 26

  2 omega   47.00   72.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   37.0000 -150.0000 25

  3 omega  -25.00   15.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   30.0000 -180.0000 40

  4 omega -118.00  -76.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  178.0000   60.0000 42

  5 omega  -98.00  -28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -30.0000  150.0000 70

  6 omega   61.00   87.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000 -131.0000    0.0000 26

  7 omega   44.00   69.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000 -120.0000 25

  8 omega  105.00  177.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000  -90.0000 72

  9 omega   62.00   88.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000 -120.0000 26

 10 omega   80.00  173.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   15.0000  -90.0000 93

 11 omega   83.00  116.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000 -120.0000 33

 12 omega   52.00   81.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  120.0000 29

 13 omega   43.00   80.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000   90.0000 37

 14 omega -114.00  -88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  178.0000  -90.0000 26

 15 omega  -79.00  -38.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  178.0000  -90.0000 41

 16 omega   32.00   71.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       55.7033   77.0000  150.0000 39

 17 omega   46.00   72.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.4066  -50.0000 -150.0000 26

 18 omega   79.00  133.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.4066  178.0000 -150.0000 54

 19 omega   63.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.4066  -50.0000  -30.0000 26

 20 omega   39.00   92.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.4066  -37.0000 -180.0000 53

 21 omega  114.00  140.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.4066  178.0000  120.0000 26

 22 omega  101.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  178.0000   90.0000 48

 23 omega   59.00   85.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000 -180.0000 26

 24 omega  112.00  141.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000 -180.0000 29

 25 omega   94.00  144.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   50.0000 -180.0000 50

 26 omega   88.00  101.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  -90.0000 13
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0415838000
_diffrn_orient_matrix_UB_12      -0.1211998000
_diffrn_orient_matrix_UB_13      0.0027974000
_diffrn_orient_matrix_UB_21      0.0580459000
_diffrn_orient_matrix_UB_22      -0.0867871000
_diffrn_orient_matrix_UB_23      0.0017798000
_diffrn_orient_matrix_UB_31      -0.0000465000
_diffrn_orient_matrix_UB_32      0.0018869000
_diffrn_orient_matrix_UB_33      0.2591807000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            5547
_diffrn_reflns_theta_full        72.19
_diffrn_reflns_theta_max         72.18
_diffrn_reflns_theta_min         4.10
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_exptl_absorpt_coefficient_mu    1.989
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86079
_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    1.260
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         1997
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0354
_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^)+(0.0539P)^2^+0.0377P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0911
_refine_ls_wR_factor_ref         0.0955
_reflns_number_gt                1816
_reflns_number_total             1997
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo402745b_si_002.cif
_cod_data_source_block           201309131
_cod_depositor_comments
;Adding full bibliography for
 ./tmp-cod-update-bibliographies-12971/cifs/4029259.cif.
;
_cod_original_cell_volume        1325.12(12)
_cod_database_code               4029259
_chemical_oxdiff_formula         C20H20N4O4S1
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C11(H11), C12(H12), C14(H14),
 C15(H15)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;