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_1514712
_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_formula_moiety         'C15 H17 N5 O2'
_chemical_formula_sum            'C15 H17 N5 O2'
_chemical_formula_weight         299.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-08-09
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Olex2 1.1
(compiled 2011.11.01 svn.r2039, GUI svn.r3906)
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_cell_length_c                   19.4702(11)
_cell_measurement_reflns_used    1431
_cell_measurement_temperature    293(2)
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_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)
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CrysAlisPro, Agilent Technologies,
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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
;
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
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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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
1 omega -10.00 24.00 1.0000 8.0000
omega____ theta____ kappa____ phi______ frames
- -16.8924 -99.0000 -180.0000 34
2 omega -48.00 42.00 1.0000 8.0000
omega____ theta____ kappa____ phi______ frames
- 19.8611 -37.0000 120.0000 90
3 omega -22.00 81.00 1.0000 8.0000
omega____ theta____ kappa____ phi______ frames
- 19.8611 19.0000 -39.0000 103
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0277287000
_diffrn_orient_matrix_UB_12      0.0137805000
_diffrn_orient_matrix_UB_13      0.0295449000
_diffrn_orient_matrix_UB_21      -0.0605378000
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_diffrn_orient_matrix_UB_23      -0.0210568000
_diffrn_orient_matrix_UB_31      0.0090527000
_diffrn_orient_matrix_UB_32      -0.0981865000
_diffrn_orient_matrix_UB_33      0.0086414000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0279
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_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
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_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            6064
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.10
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76276
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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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)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2938
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0827
_refine_ls_R_factor_gt           0.0546
_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^)+(0.0705P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1281
_refine_ls_wR_factor_ref         0.1519
_reflns_number_gt                1973
_reflns_number_total             2938
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3sc50348h.txt
_cod_data_source_block           120809_s4_2230
_cod_original_cell_volume        1437.95(13)
_cod_database_code               1514712
_chemical_oxdiff_formula         C12H10N4O3
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32