Iridium-catalyzed C-H borylation of pyridines.
Sadler, Scott A.; Tajuddin, Hazmi; Mkhalid, Ibraheem A. I.; Batsanov, Andrei S.; Albesa-Jove, David; Cheung, Man Sing; Maxwell, Aoife C.; Shukla, Lena; Roberts, Bryan; Blakemore, David C.; Lin, Zhenyang; Marder, Todd B.; Steel, Patrick G.; Organic & biomolecular chemistry 12 (2014) 7318–7327; doi:10.1039/c4ob01565g

data_7154056
_publ_section_title
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 Iridium-catalyzed C-H borylation of pyridines.
;
_journal_issue                   37
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7318
_journal_page_last               7327
_journal_paper_doi               10.1039/c4ob01565g
_journal_volume                  12
_journal_year                    2014
_chemical_formula_moiety         'C10 H10 N2 S'
_chemical_formula_sum            'C10 H10 N2 S'
_chemical_formula_weight         190.26
_chemical_melting_point          324
_chemical_name_systematic
;
 2,3-dimethy-5-thiophen-2-yl-pyrazine
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-02-24
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2014.02.17 svn.r2891 for OlexSys, GUI svn.r4773)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.168(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1352(19)
_cell_length_b                   12.292(3)
_cell_length_c                   11.175(3)
_cell_measurement_reflns_used    868
_cell_measurement_temperature    250
_cell_measurement_theta_max      29.258
_cell_measurement_theta_min      3.303
_cell_volume                     977.5(4)
_computing_cell_refinement       'SMART V5.625 (Bruker, 2001)'
_computing_data_collection       'SMART version 4.05 (Siemens, 1995)'
_computing_data_reduction        'SAINT V6.45 (Bruker, 2001)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_temperature      250
_diffrn_detector_area_resol_mean 7.9
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'SMART 1000 CCD area detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7011
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.994
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_min         2.467
_exptl_absorpt_coefficient_mu    0.283
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         1720
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0372
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0516P)^2^+0.2351P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1006
_refine_ls_wR_factor_ref         0.1076
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1411
_reflns_number_total             1720
_reflns_threshold_expression     'I > 2\s(I)'
_cod_duplicate_entry             7153981
_cod_data_source_file            c4ob01565g2.cif
_cod_data_source_block           S14
_cod_database_code               7154056
_shelxl_version_number           2014-1
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Uiso(H9A)=Uiso(H9B)=Uiso(H9C)=FVAR(1)
 Uiso(H10A)=Uiso(H10B)=Uiso(H10C)=FVAR(2)
3.a Rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C8(H8)
;
_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'