#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:59:37 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180326 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/40/7154055.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7154055
loop_
_publ_author_name
'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.'
_publ_section_title
;
 Iridium-catalyzed C-H borylation of pyridines.
;
_journal_issue                   37
_journal_name_full               'Organic & 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       'ω 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/[σ²(Fo²)+(0.0908P)²] where P=(Fo²+2Fc²)/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 > 2σ(I)'
_cod_duplicate_entry             7153980
_cod_data_source_file            c4ob01565g2.cif
_cod_data_source_block           S13
_cod_database_code               7154055
#BEGIN Tags that were not found in dictionaries:
_shelxl_version_number           2014-1
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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)'
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O 0.5708(2) 0.9348(7) 0.1512(3) 0.0250(12) Uani 1 1 d . .
O2 O 0.6167(2) 0.6203(8) 0.1473(3) 0.0271(12) Uani 1 1 d . .
O3 O 0.1732(2) 0.5801(7) 0.4372(3) 0.0220(11) Uani 1 1 d . .
O4 O 0.1352(2) 0.9007(7) 0.4474(3) 0.0253(12) Uani 1 1 d . .
N1 N 0.4016(3) 0.4989(9) 0.3112(4) 0.0209(13) Uani 1 1 d . .
N2 N 0.3467(3) 1.0038(9) 0.2762(3) 0.0214(13) Uani 1 1 d . .
B1 B 0.5667(4) 0.7376(11) 0.1736(6) 0.016(2) Uani 1 1 d . .
B2 B 0.1819(5) 0.7749(13) 0.4173(6) 0.019(2) Uani 1 1 d . .
C1 C 0.3445(3) 0.8125(12) 0.3035(4) 0.0180(14) Uani 1 1 d . .
C2 C 0.4028(3) 0.6899(12) 0.2847(5) 0.0208(15) Uani 1 1 d . .
C3 C 0.4549(4) 0.7679(10) 0.2409(5) 0.0155(18) Uani 1 1 d . .
H3 H 0.4541 0.9039 0.2227 0.019 Uiso 1 1 calc R .
C4 C 0.5080(3) 0.6496(11) 0.2234(4) 0.0200(15) Uani 1 1 d . .
C5 C 0.5061(3) 0.4526(10) 0.2511(4) 0.0206(14) Uani 1 1 d . .
H5 H 0.5412 0.3655 0.2403 0.025 Uiso 1 1 calc R .
C6 C 0.4529(3) 0.3821(11) 0.2946(4) 0.0243(16) Uani 1 1 d . .
H6 H 0.4526 0.2465 0.3134 0.029 Uiso 1 1 calc R .
C7 C 0.6547(4) 0.7467(10) 0.0891(6) 0.019(2) Uani 1 1 d . .
C8 C 0.6354(3) 0.9631(12) 0.1189(5) 0.0249(17) Uani 1 1 d . .
C9 C 0.6764(4) 1.0370(13) 0.1921(5) 0.039(2) Uani 1 1 d . .
H9A H 0.6608 1.1684 0.2110 0.049(13) Uiso 1 1 d GR .
H9B H 0.7211 1.0491 0.1737 0.049(13) Uiso 1 1 d GR .
H9C H 0.6737 0.9408 0.2388 0.049(13) Uiso 1 1 d GR .
C10 C 0.6354(4) 1.1204(13) 0.0507(5) 0.038(2) Uani 1 1 d . .
H10A H 0.6194 1.2476 0.0735 0.033(13) Uiso 1 1 d GR .
H10B H 0.6078 1.0765 0.0043 0.033(13) Uiso 1 1 d GR .
H10C H 0.6793 1.1392 0.0298 0.033(13) Uiso 1 1 d GR .
C11 C 0.6297(4) 0.7026(15) 0.0026(5) 0.037(2) Uani 1 1 d . .
H11A H 0.6345 0.5588 -0.0093 0.046(15) Uiso 1 1 d GR .
H11B H 0.6539 0.7804 -0.0391 0.046(15) Uiso 1 1 d GR .
H11C H 0.5842 0.7394 -0.0004 0.046(15) Uiso 1 1 d GR .
C12 C 0.7247(4) 0.6944(14) 0.0988(6) 0.041(2) Uani 1 1 d . .
H12A H 0.7375 0.7131 0.1577 0.058(15) Uiso 1 1 d GR .
H12B H 0.7506 0.7821 0.0626 0.058(15) Uiso 1 1 d GR .
H12C H 0.7315 0.5540 0.0825 0.058(15) Uiso 1 1 d GR .
C13 C 0.2922(4) 0.7371(10) 0.3468(5) 0.0167(19) Uani 1 1 d . .
H13 H 0.2920 0.6003 0.3639 0.020 Uiso 1 1 calc R .
C14 C 0.2402(3) 0.8583(11) 0.3655(4) 0.0194(14) Uani 1 1 d . .
C15 C 0.2430(3) 1.0575(11) 0.3387(4) 0.0229(15) Uani 1 1 d . .
H15 H 0.2089 1.1477 0.3509 0.027 Uiso 1 1 calc R .
C16 C 0.2962(3) 1.1217(11) 0.2941(5) 0.0239(16) Uani 1 1 d . .
H16 H 0.2970 1.2569 0.2749 0.029 Uiso 1 1 calc R .
C17 C 0.0973(4) 0.7770(11) 0.5062(6) 0.0213(19) Uani 1 1 d . U
C18 C 0.1091(3) 0.5642(11) 0.4735(5) 0.0213(15) Uani 1 1 d . .
C19 C 0.0651(3) 0.5051(14) 0.4016(5) 0.035(2) Uani 1 1 d . .
H19A H 0.0811 0.3819 0.3752 0.048(14) Uiso 1 1 d GR .
H19B H 0.0640 0.6134 0.3598 0.048(14) Uiso 1 1 d GR .
H19C H 0.0217 0.4817 0.4233 0.048(14) Uiso 1 1 d GR .
C20 C 0.1096(3) 0.3997(11) 0.5402(4) 0.0276(17) Uani 1 1 d . .
H20A H 0.1202 0.2708 0.5137 0.044(14) Uiso 1 1 d GR .
H20B H 0.0673 0.3907 0.5667 0.044(14) Uiso 1 1 d GR .
H20C H 0.1419 0.4313 0.5832 0.044(14) Uiso 1 1 d GR .
C21 C 0.0278(3) 0.8497(12) 0.5042(5) 0.0362(19) Uani 1 1 d . .
H21A H 0.0257 0.9879 0.5254 0.027(11) Uiso 1 1 d GR .
H21B H 0.0014 0.7623 0.5398 0.027(11) Uiso 1 1 d GR .
H21C H 0.0117 0.8457 0.4462 0.027(11) Uiso 1 1 d GR .
C22 C 0.1258(4) 0.8156(14) 0.5940(5) 0.0322(19) Uani 1 1 d . .
H22A H 0.1706 0.7710 0.5952 0.045(14) Uiso 1 1 d GR .
H22B H 0.1012 0.7409 0.6362 0.045(14) Uiso 1 1 d GR .
H22C H 0.1238 0.9597 0.6067 0.045(14) Uiso 1 1 d GR .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0010 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
B1 O1 C8 105.9(6)
B1 O2 C7 105.9(6)
B2 O3 C18 106.7(6)
B2 O4 C17 105.1(6)
C2 N1 C6 118.2(6)
C16 N2 C1 117.2(6)
O1 B1 O2 115.0(8)
O1 B1 C4 122.6(7)
O2 B1 C4 122.4(6)
O3 B2 O4 114.2(8)
O3 B2 C14 124.6(7)
O4 B2 C14 121.2(7)
N2 C1 C2 115.1(5)
N2 C1 C13 122.0(7)
C13 C1 C2 122.9(6)
N1 C2 C1 116.2(5)
N1 C2 C3 121.7(7)
C3 C2 C1 122.1(6)
C2 C3 H3 119.6
C4 C3 C2 120.8(7)
C4 C3 H3 119.6
C3 C4 B1 120.8(6)
C5 C4 B1 122.4(6)
C5 C4 C3 116.8(6)
C4 C5 H5 119.9
C4 C5 C6 120.1(6)
C6 C5 H5 119.9
N1 C6 C5 122.4(7)
N1 C6 H6 118.8
C5 C6 H6 118.8
O2 C7 C8 101.3(6)
O2 C7 C11 105.9(6)
O2 C7 C12 108.9(6)
C11 C7 C8 111.6(7)
C11 C7 C12 112.6(7)
C12 C7 C8 115.4(7)
O1 C8 C7 103.0(6)
O1 C8 C9 107.0(6)
O1 C8 C10 110.1(6)
C9 C8 C7 112.5(6)
C10 C8 C7 114.9(7)
C10 C8 C9 108.9(7)
C8 C9 H9A 109.5
C8 C9 H9B 109.4
C8 C9 H9C 109.5
H9A C9 H9B 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C8 C10 H10A 109.5
C8 C10 H10B 109.5
C8 C10 H10C 109.4
H10A C10 H10B 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C7 C11 H11A 109.4
C7 C11 H11B 109.6
C7 C11 H11C 109.4
H11A C11 H11B 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C7 C12 H12A 109.4
C7 C12 H12B 109.6
C7 C12 H12C 109.4
H12A C12 H12B 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C1 C13 H13 119.6
C1 C13 C14 120.9(7)
C14 C13 H13 119.6
C13 C14 B2 120.9(7)
C13 C14 C15 117.2(6)
C15 C14 B2 121.9(6)
C14 C15 H15 120.5
C16 C15 C14 118.9(7)
C16 C15 H15 120.5
N2 C16 C15 123.8(7)
N2 C16 H16 118.1
C15 C16 H16 118.1
O4 C17 C18 102.4(6)
O4 C17 C21 108.5(7)
O4 C17 C22 105.9(6)
C18 C17 C21 116.0(7)
C18 C17 C22 113.6(7)
C21 C17 C22 109.5(7)
O3 C18 C17 102.4(6)
O3 C18 C19 106.0(6)
O3 C18 C20 108.7(5)
C19 C18 C17 113.5(6)
C19 C18 C20 109.9(6)
C20 C18 C17 115.5(7)
C18 C19 H19A 109.4
C18 C19 H19B 109.5
C18 C19 H19C 109.5
H19A C19 H19B 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
C18 C20 H20A 109.3
C18 C20 H20B 109.6
C18 C20 H20C 109.5
H20A C20 H20B 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
C17 C21 H21A 109.4
C17 C21 H21B 109.4
C17 C21 H21C 109.6
H21A C21 H21B 109.5
H21A C21 H21C 109.5
H21B C21 H21C 109.5
C17 C22 H22A 109.6
C17 C22 H22B 109.4
C17 C22 H22C 109.4
H22A C22 H22B 109.5
H22A C22 H22C 109.5
H22B C22 H22C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 B1 1.362(9)
O1 C8 1.455(8)
O2 B1 1.367(10)
O2 C7 1.479(9)
O3 B2 1.347(10)
O3 C18 1.458(8)
O4 B2 1.370(11)
O4 C17 1.474(9)
N1 C2 1.338(10)
N1 C6 1.348(9)
N2 C1 1.346(10)
N2 C16 1.345(9)
B1 C4 1.571(11)
B2 C14 1.569(12)
C1 C2 1.493(7)
C1 C13 1.383(10)
C2 C3 1.391(11)
C3 H3 0.9500
C3 C4 1.386(10)
C4 C5 1.382(10)
C5 H5 0.9500
C5 C6 1.388(9)
C6 H6 0.9500
C7 C8 1.568(10)
C7 C11 1.499(13)
C7 C12 1.509(11)
C8 C9 1.523(10)
C8 C10 1.506(11)
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
C10 H10A 0.9798
C10 H10B 0.9800
C10 H10C 0.9801
C11 H11A 0.9800
C11 H11B 0.9801
C11 H11C 0.9800
C12 H12A 0.9800
C12 H12B 0.9800
C12 H12C 0.9800
C13 H13 0.9500
C13 C14 1.383(10)
C14 C15 1.393(10)
C15 H15 0.9500
C15 C16 1.383(9)
C16 H16 0.9500
C17 C18 1.528(11)
C17 C21 1.529(11)
C17 C22 1.536(12)
C18 C19 1.517(10)
C18 C20 1.523(11)
C19 H19A 0.9799
C19 H19B 0.9800
C19 H19C 0.9800
C20 H20A 0.9800
C20 H20B 0.9798
C20 H20C 0.9799
C21 H21A 0.9801
C21 H21B 0.9799
C21 H21C 0.9798
C22 H22A 0.9800
C22 H22B 0.9802
C22 H22C 0.9800
