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_7153980
_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_absolute_configuration unk
_chemical_formula_moiety         'C22 H30 B2 N2 O4'
_chemical_formula_sum            'C22 H30 B2 N2 O4'
_chemical_formula_weight         408.10
_chemical_name_systematic
;
 4,4'-bis(Bpin)-2,2'-bipyridine
;
_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   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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.849(4)
_cell_length_b                   6.6532(12)
_cell_length_c                   15.874(3)
_cell_measurement_reflns_used    793
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.76
_cell_measurement_theta_min      3.23
_cell_volume                     2201.9(7)
_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      120
_diffrn_detector_area_resol_mean 7.9
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0799
_diffrn_reflns_av_unetI/netI     0.0861
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10891
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.954
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_description       needle
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.584
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details
;
 Flack x determined using 879 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
 Absolute polarity undeterminable.
;
_refine_ls_abs_structure_Flack   -0.2(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     287
_refine_ls_number_reflns         3720
_refine_ls_number_restraints     154
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.1096
_refine_ls_R_factor_gt           0.0693
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0908P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1501
_refine_ls_wR_factor_ref         0.1724
_reflns_Friedel_coverage         0.850
_reflns_Friedel_fraction_full    0.919
_reflns_Friedel_fraction_max     0.919
_reflns_number_gt                2515
_reflns_number_total             3720
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4ob01565g2.cif
_cod_data_source_block           S13
_cod_depositor_comments
'Adding full bibliography for 7153976--7153981.cif.'
_cod_database_code               7153980
_shelxl_version_number           2014-1
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C17) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
3. Rigid body (RIGU) restrains
 C18, O3, O4, C20, C19, C22, C21, C17
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N2, C1, C13, C14, C15, C16, B2, N1, C2, C3, C4, C5, C6, B1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Uiso(H9A)=Uiso(H9B)=Uiso(H9C)=FVAR(1)
 Uiso(H10A)=Uiso(H10B)=Uiso(H10C)=FVAR(2)
 Uiso(H11A)=Uiso(H11B)=Uiso(H11C)=FVAR(3)
 Uiso(H12A)=Uiso(H12B)=Uiso(H12C)=FVAR(4)
 Uiso(H19A)=Uiso(H19B)=Uiso(H19C)=FVAR(5)
 Uiso(H20A)=Uiso(H20B)=Uiso(H20C)=FVAR(6)
 Uiso(H21A)=Uiso(H21B)=Uiso(H21C)=FVAR(7)
 Uiso(H22A)=Uiso(H22B)=Uiso(H22C)=FVAR(8)
5.a Rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,
 H12C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,
 H22B,H22C)
5.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C13(H13), C15(H15), C16(H16)
;
_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'