#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:59:37 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180326 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/40/7154052.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_7154052
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_formula_moiety         'C11 H14 B Cl2 N O2'
_chemical_formula_sum            'C11 H14 B Cl2 N O2'
_chemical_formula_weight         273.94
_chemical_melting_point          322
_chemical_name_common            2,3-Dichloro-5-(Bpin)-pyridine
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 93.137(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.5381(4)
_cell_length_b                   21.3579(12)
_cell_length_c                   9.4192(5)
_cell_measurement_reflns_used    974
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      30.11
_cell_measurement_theta_min      2.88
_cell_volume                     1313.33(13)
_computing_cell_refinement       'SMART V5.625 (Bruker, 2001)'
_computing_data_collection       'SMART V5.625 (Bruker, 2001)'
_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      120.15
_diffrn_detector_area_resol_mean 5.6
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'SMART 6000 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  0.0285
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            18635
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        30.000
_diffrn_reflns_theta_max         30.504
_diffrn_reflns_theta_min         2.366
_exptl_absorpt_coefficient_mu    0.482
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rhombohedron
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         4008
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0313
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0412P)²+0.2801P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0782
_refine_ls_wR_factor_ref         0.0826
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3283
_reflns_number_total             4008
_reflns_threshold_expression     'I > 2σ(I)'
_cod_duplicate_entry             7153977
_cod_data_source_file            c4ob01565g2.cif
_cod_data_source_block           39e
_cod_database_code               7154052
#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. Others
 Uiso(H8A)=Uiso(H8B)=Uiso(H8C)=FVAR(1)
 Uiso(H9A)=Uiso(H9B)=Uiso(H9C)=FVAR(2)
 Uiso(H10A)=Uiso(H10B)=Uiso(H10C)=FVAR(3)
 Uiso(H11A)=Uiso(H11B)=Uiso(H11C)=FVAR(4)
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5)
3.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
Cl1 Cl -0.15047(5) 1.14081(2) 0.52649(3) 0.02851(8) Uani 1 1 d .
Cl2 Cl 0.31112(5) 1.10773(2) 0.47458(4) 0.03210(9) Uani 1 1 d .
O1 O 0.13112(12) 0.87948(4) 0.90842(9) 0.02309(17) Uani 1 1 d .
O2 O 0.44678(12) 0.90714(4) 0.83368(9) 0.02157(16) Uani 1 1 d .
B B 0.2429(2) 0.92040(6) 0.83270(13) 0.0204(2) Uani 1 1 d .
C1 C -0.03213(18) 1.07733(5) 0.61177(12) 0.0211(2) Uani 1 1 d .
C2 C 0.17194(17) 1.06413(5) 0.58920(12) 0.0208(2) Uani 1 1 d .
C3 C 0.26265(17) 1.01373(5) 0.66135(12) 0.0211(2) Uani 1 1 d .
H3 H 0.4023 1.0038 0.6497 0.025 Uiso 1 1 calc R
C4 C 0.14644(17) 0.97779(5) 0.75137(12) 0.0203(2) Uani 1 1 d .
C5 C -0.05747(18) 0.99537(5) 0.76337(13) 0.0241(2) Uani 1 1 d .
H5 H -0.1385 0.9710 0.8232 0.029 Uiso 1 1 calc R
N N -0.14682(16) 1.04442(5) 0.69601(11) 0.0250(2) Uani 1 1 d .
C6 C 0.26782(17) 0.82679(5) 0.94563(12) 0.0209(2) Uani 1 1 d .
C7 C 0.48432(17) 0.85690(5) 0.93806(12) 0.0197(2) Uani 1 1 d .
C8 C 0.22418(19) 0.77625(6) 0.83404(14) 0.0278(3) Uani 1 1 d .
H8A H 0.0787 0.7650 0.8319 0.037(2) Uiso 1 1 calc GR
H8B H 0.3076 0.7392 0.8579 0.037(2) Uiso 1 1 calc GR
H8C H 0.2582 0.7920 0.7405 0.037(2) Uiso 1 1 calc GR
C9 C 0.2179(2) 0.80296(7) 1.09152(14) 0.0324(3) Uani 1 1 d .
H9A H 0.2315 0.8373 1.1605 0.042(3) Uiso 1 1 calc GR
H9B H 0.3128 0.7692 1.1203 0.042(3) Uiso 1 1 calc GR
H9C H 0.0771 0.7870 1.0879 0.042(3) Uiso 1 1 calc GR
C10 C 0.5613(2) 0.88833(6) 1.07598(14) 0.0316(3) Uani 1 1 d .
H10A H 0.6842 0.9129 1.0591 0.045(3) Uiso 1 1 calc GR
H10B H 0.5946 0.8563 1.1480 0.045(3) Uiso 1 1 calc GR
H10C H 0.4546 0.9160 1.1096 0.045(3) Uiso 1 1 calc GR
C11 C 0.64764(19) 0.81402(6) 0.88421(15) 0.0272(2) Uani 1 1 d .
H11A H 0.6051 0.7992 0.7887 0.038(3) Uiso 1 1 calc GR
H11B H 0.6665 0.7781 0.9484 0.038(3) Uiso 1 1 calc GR
H11C H 0.7769 0.8370 0.8807 0.038(3) Uiso 1 1 calc GR
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.03247(16) 0.02131(13) 0.03140(15) 0.00410(11) -0.00148(12) 0.00477(10)
Cl2 0.03123(16) 0.02903(15) 0.03676(17) 0.01003(12) 0.00845(12) -0.00418(11)
O1 0.0195(4) 0.0225(4) 0.0274(4) 0.0054(3) 0.0027(3) 0.0025(3)
O2 0.0206(4) 0.0195(4) 0.0248(4) 0.0042(3) 0.0037(3) 0.0003(3)
B 0.0219(6) 0.0195(5) 0.0199(5) -0.0011(4) 0.0017(4) 0.0004(4)
C1 0.0251(5) 0.0169(5) 0.0211(5) -0.0006(4) -0.0013(4) 0.0012(4)
C2 0.0237(5) 0.0181(5) 0.0208(5) -0.0002(4) 0.0023(4) -0.0037(4)
C3 0.0208(5) 0.0190(5) 0.0234(5) -0.0014(4) 0.0010(4) -0.0002(4)
C4 0.0235(5) 0.0175(5) 0.0201(5) -0.0012(4) 0.0009(4) 0.0003(4)
C5 0.0245(5) 0.0225(5) 0.0259(5) 0.0029(4) 0.0049(4) 0.0007(4)
N 0.0248(5) 0.0232(5) 0.0272(5) 0.0024(4) 0.0042(4) 0.0029(4)
C6 0.0195(5) 0.0203(5) 0.0228(5) 0.0044(4) 0.0008(4) 0.0012(4)
C7 0.0197(5) 0.0185(5) 0.0210(5) 0.0018(4) 0.0004(4) -0.0003(4)
C8 0.0269(6) 0.0205(5) 0.0354(6) 0.0009(5) -0.0055(5) -0.0027(4)
C9 0.0281(6) 0.0404(7) 0.0292(6) 0.0144(5) 0.0058(5) 0.0008(5)
C10 0.0324(6) 0.0341(7) 0.0275(6) -0.0049(5) -0.0060(5) -0.0028(5)
C11 0.0214(5) 0.0226(5) 0.0380(7) 0.0010(5) 0.0044(5) 0.0026(4)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
B O1 C6 106.22(9)
B O2 C7 106.52(8)
O1 B C4 123.09(10)
O2 B O1 114.52(10)
O2 B C4 122.40(10)
C2 C1 Cl1 119.62(9)
N C1 Cl1 116.07(9)
N C1 C2 124.31(10)
C1 C2 Cl2 122.01(9)
C3 C2 Cl2 119.98(9)
C3 C2 C1 118.02(10)
C2 C3 H3 120.3
C2 C3 C4 119.38(10)
C4 C3 H3 120.3
C3 C4 B 120.70(10)
C5 C4 B 122.27(10)
C5 C4 C3 117.04(10)
C4 C5 H5 117.8
N C5 C4 124.39(11)
N C5 H5 117.8
C1 N C5 116.87(10)
O1 C6 C7 102.43(8)
O1 C6 C8 106.86(9)
O1 C6 C9 108.37(10)
C8 C6 C7 113.39(9)
C9 C6 C7 114.86(10)
C9 C6 C8 110.23(10)
O2 C7 C6 102.31(8)
O2 C7 C10 106.54(9)
O2 C7 C11 108.23(9)
C10 C7 C6 113.64(10)
C11 C7 C6 115.08(9)
C11 C7 C10 110.24(10)
C6 C8 H8A 109.5
C6 C8 H8B 109.5
C6 C8 H8C 109.5
H8A C8 H8B 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C6 C9 H9A 109.5
C6 C9 H9B 109.5
C6 C9 H9C 109.5
H9A C9 H9B 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C7 C10 H10A 109.5
C7 C10 H10B 109.5
C7 C10 H10C 109.5
H10A C10 H10B 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C7 C11 H11A 109.5
C7 C11 H11B 109.5
C7 C11 H11C 109.5
H11A C11 H11B 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.7363(11)
Cl2 C2 1.7230(11)
O1 B 1.3651(15)
O1 C6 1.4676(13)
O2 B 1.3623(15)
O2 C7 1.4670(13)
B C4 1.5601(17)
C1 C2 1.3914(16)
C1 N 1.3232(15)
C2 C3 1.3886(15)
C3 H3 0.9500
C3 C4 1.3986(16)
C4 C5 1.3956(16)
C5 H5 0.9500
C5 N 1.3420(15)
C6 C7 1.5600(16)
C6 C8 1.5227(17)
C6 C9 1.5176(16)
C7 C10 1.5231(16)
C7 C11 1.5151(16)
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
