Pd-catalyzed oxidative C‒H/C‒H cross-coupling of pyridines with heteroarenes
Liu, Bo; Huang, Yumin; Lan, Jingbo; Song, Feijie; You, Jingsong; Chemical Science 4 (2013) 2163–; doi:10.1039/c3sc50348h

data_1514715
_publ_section_title
;
 Pd-catalyzed oxidative C--H/C--H cross-coupling of pyridines with
 heteroarenes
;
_journal_issue                   5
_journal_name_full               'Chemical Science'
_journal_page_first              2163
_journal_paper_doi               10.1039/c3sc50348h
_journal_volume                  4
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H12 N O2 S'
_chemical_formula_sum            'C16 H12 N O2 S'
_chemical_formula_weight         282.33
_chemical_name_systematic
;
?
;
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_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             2012-09-04
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Olex2 1.1
(compiled 2011.11.01 svn.r2039, GUI svn.r3906)
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_cell_angle_gamma                72.375(6)
_cell_formula_units_Z            2
_cell_length_a                   6.0479(4)
_cell_length_b                   8.1021(5)
_cell_length_c                   14.5564(10)
_cell_measurement_reflns_used    1465
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.8920
_cell_measurement_theta_min      3.1530
_cell_volume                     670.83(8)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
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_computing_molecular_graphics
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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
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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
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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      293.15
_diffrn_detector_area_resol_mean 16.0874
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
1 omega -24.00 19.00 1.0000 6.0000
omega____ theta____ kappa____ phi______ frames
- -16.8924 -99.0000 -90.0000 43
2 omega -90.00 -35.00 1.0000 6.0000
omega____ theta____ kappa____ phi______ frames
- -16.8924 -178.0000 -120.0000 55
3 omega -25.00 21.00 1.0000 6.0000
omega____ theta____ kappa____ phi______ frames
- -16.8924 -99.0000 30.0000 46
4 omega -92.00 -53.00 1.0000 6.0000
omega____ theta____ kappa____ phi______ frames
- -16.8924 -178.0000 150.0000 39
5 omega -5.00 90.00 1.0000 6.0000
omega____ theta____ kappa____ phi______ frames
- 20.0174 37.0000 -150.0000 95
6 omega -31.00 64.00 1.0000 6.0000
omega____ theta____ kappa____ phi______ frames
- 20.0174 -19.0000 0.0000 95
7 omega -52.00 10.00 1.0000 6.0000
omega____ theta____ kappa____ phi______ frames
- 20.0174 -37.0000 150.0000 62
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0174768000
_diffrn_orient_matrix_UB_12      -0.0282825000
_diffrn_orient_matrix_UB_13      -0.0417749000
_diffrn_orient_matrix_UB_21      -0.1165453000
_diffrn_orient_matrix_UB_22      0.0544417000
_diffrn_orient_matrix_UB_23      0.0016238000
_diffrn_orient_matrix_UB_31      0.0364081000
_diffrn_orient_matrix_UB_32      0.0692686000
_diffrn_orient_matrix_UB_33      -0.0262769000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0171
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5668
_diffrn_reflns_theta_full        26.36
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         3.16
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.241
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98593
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             294
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.626
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.089
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.22(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         4305
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.1016
_refine_ls_R_factor_gt           0.0796
_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^)+(0.1494P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2035
_refine_ls_wR_factor_ref         0.2322
_reflns_number_gt                3238
_reflns_number_total             4305
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3sc50348h.txt
_cod_data_source_block           1
_cod_database_code               1514715
_chemical_oxdiff_formula         C12H10N4O3S1
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32