#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:59:37 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180326 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/40/7154051.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_7154051
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         'C13 H20 B N O2'
_chemical_formula_sum            'C13 H20 B N O2'
_chemical_formula_weight         233.11
_chemical_melting_point          354
_chemical_name_common            2,6-dimethyl-4-(Bpin)-pyridine
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 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                 93.085(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.9952(15)
_cell_length_b                   6.8431(13)
_cell_length_c                   12.251(2)
_cell_measurement_reflns_used    763
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      30.08
_cell_measurement_theta_min      25.05
_cell_volume                     669.3(2)
_computing_cell_refinement       'SMART V5.625 (Bruker, 2001)'
_computing_data_collection       'SMART V5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT V6.45 (Bruker, 2003)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelxS (Sheldrick, 2008)'
_diffrn_ambient_temperature      120.15
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'ProteumM APEX CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source
'60W microfocus Bede Microsource with glass polycapillary optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3959
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.496
_diffrn_reflns_theta_min         2.971
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.157
_exptl_crystal_description       plate
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     121
_refine_ls_number_reflns         1496
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0620
_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
'w=1/[σ²(Fo²)+(0.0730P)²+0.2640P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1382
_refine_ls_wR_factor_ref         0.1432
_reflns_number_gt                1310
_reflns_number_total             1496
_reflns_threshold_expression     'I > 2σ(I)'
_cod_duplicate_entry             7153976
_cod_data_source_file            c4ob01565g2.cif
_cod_data_source_block           5
_cod_database_code               7154051
#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
 At 1.5 times of:
  All C(H,H) groups, All C(H,H,H) groups
2. Others
 Fixed Sof: C8(0.5) C9(0.5) C10(0.5) H10A(0.5) H10B(0.5) H10C(0.5) C11(0.5)
 H11A(0.5) H11B(0.5) H11C(0.5) C12(0.5) H12A(0.5) H12B(0.5) H12C(0.5) C13(0.5)
 H13A(0.5) H13B(0.5) H13C(0.5)
3.a Riding coordinates:
 C2(H2), C4(H4), C6(H6A,H6B), C7(H7A,H7B), C10(H10A,H10B,H10C), C11(H11A,H11B,
 H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
;
_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+1/2, -z'
'-x, -y, -z'
'x, -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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B B 0.6650(3) 0.2500 0.18104(18) 0.0190(5) Uani 1 2 d S T P A .
O1 O 0.59356(16) 0.2500 0.27963(11) 0.0229(4) Uani 1 2 d S T P . .
O2 O 0.83572(16) 0.2500 0.18837(10) 0.0225(4) Uani 1 2 d S T P . .
N1 N 0.37430(19) 0.2500 -0.13179(12) 0.0182(4) Uani 1 2 d S T P A .
C1 C 0.2983(2) 0.2500 -0.03703(16) 0.0238(5) Uani 1 2 d S T P . .
C2 C 0.3869(2) 0.2500 0.06375(16) 0.0246(5) Uani 1 2 d S T P A .
H2 H 0.3283 0.2500 0.1292 0.030 Uiso 1 2 d RS T P . .
C3 C 0.5601(2) 0.2500 0.06930(15) 0.0185(4) Uani 1 2 d S T P . .
C4 C 0.6369(2) 0.2500 -0.02926(16) 0.0242(5) Uani 1 2 d S T P A .
H4 H 0.7557 0.2500 -0.0298 0.029 Uiso 1 2 d RS T P . .
C5 C 0.5418(2) 0.2500 -0.12761(16) 0.0218(5) Uani 1 2 d S T P . .
C6 C 0.1100(3) 0.2500 -0.04582(19) 0.0567(10) Uani 1 2 d S T P . .
H6A H 0.0705 0.1331 -0.0855 0.085 Uiso 1 1 d R . . . .
H6B H 0.0663 0.2500 0.0274 0.085 Uiso 1 2 d RS T P . .
C7 C 0.6223(3) 0.2500 -0.23591(18) 0.0462(8) Uani 1 2 d S T P A .
H7A H 0.5876 0.1331 -0.2774 0.069 Uiso 1 1 d R . . . .
H7B H 0.7444 0.2500 -0.2234 0.069 Uiso 1 2 d RS T P . .
C8 C 0.8882(3) 0.273(5) 0.30299(19) 0.029(4) Uani 0.5 1 d . . . A -1
C9 C 0.7277(3) 0.229(5) 0.3638(2) 0.027(5) Uani 0.5 1 d . . . A -1
C10 C 1.0404(3) 0.1541(5) 0.3308(2) 0.0306(7) Uani 0.5 1 d . . . A -1
H10A H 1.1331 0.1989 0.2909 0.046 Uiso 0.5 1 d R . . A -1
H10B H 1.0157 0.0208 0.3115 0.046 Uiso 0.5 1 d R . . A -1
H10C H 1.0687 0.1625 0.4078 0.046 Uiso 0.5 1 d R . . A -1
C11 C 0.9322(4) 0.4952(5) 0.3135(2) 0.0288(7) Uani 0.5 1 d . . . A -1
H11A H 1.0253 0.5227 0.2670 0.043 Uiso 0.5 1 d R . . A -1
H11B H 0.9661 0.5256 0.3897 0.043 Uiso 0.5 1 d R . . A -1
H11C H 0.8353 0.5757 0.2904 0.043 Uiso 0.5 1 d R . . A -1
C12 C 0.7200(4) 0.0056(5) 0.3922(2) 0.0308(7) Uani 0.5 1 d . . . A -1
H12A H 0.8087 -0.0280 0.4473 0.046 Uiso 0.5 1 d R . . A -1
H12B H 0.7344 -0.0732 0.3264 0.046 Uiso 0.5 1 d R . . A -1
H12C H 0.6104 -0.0207 0.4213 0.046 Uiso 0.5 1 d R . . A -1
C13 C 0.6933(4) 0.3465(5) 0.4617(2) 0.0294(7) Uani 0.5 1 d . . . A -1
H13A H 0.5896 0.3036 0.4898 0.044 Uiso 0.5 1 d R . . A -1
H13B H 0.7817 0.3338 0.5174 0.044 Uiso 0.5 1 d R . . A -1
H13C H 0.6858 0.4807 0.4391 0.044 Uiso 0.5 1 d R . . A -1
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
B 0.0200(10) 0.0161(11) 0.0208(11) 0.000 -0.0004(8) 0.000
O1 0.0196(7) 0.0311(8) 0.0177(7) 0.000 -0.0020(5) 0.000
O2 0.0208(7) 0.0310(8) 0.0152(7) 0.000 -0.0022(5) 0.000
N1 0.0183(8) 0.0165(8) 0.0194(8) 0.000 -0.0017(6) 0.000
C1 0.0184(10) 0.0317(12) 0.0212(10) 0.000 0.0002(7) 0.000
C2 0.0207(10) 0.0359(12) 0.0173(9) 0.000 0.0024(7) 0.000
C3 0.0209(10) 0.0137(9) 0.0205(9) 0.000 -0.0026(7) 0.000
C4 0.0158(9) 0.0338(12) 0.0227(10) 0.000 -0.0004(7) 0.000
C5 0.0190(9) 0.0254(11) 0.0209(10) 0.000 0.0005(7) 0.000
C6 0.0171(11) 0.130(3) 0.0229(12) 0.000 0.0005(9) 0.000
C7 0.0192(11) 0.097(2) 0.0224(11) 0.000 0.0017(8) 0.000
C8 0.0220(11) 0.049(13) 0.0152(10) 0.003(2) -0.0041(8) 0.010(4)
C9 0.0218(11) 0.041(14) 0.0175(10) -0.006(3) -0.0041(8) -0.002(2)
C10 0.0231(14) 0.0397(18) 0.0284(15) 0.0030(13) -0.0033(11) 0.0080(13)
C11 0.0315(15) 0.0271(17) 0.0272(14) 0.0022(12) -0.0048(11) -0.0075(13)
C12 0.0379(17) 0.0282(17) 0.0257(14) 0.0033(13) -0.0045(12) -0.0048(13)
C13 0.0300(15) 0.0374(17) 0.0209(13) -0.0056(13) 0.0015(11) 0.0009(13)
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 B C3 122.94(17)
O2 B O1 114.05(16)
O2 B C3 123.01(17)
B O1 C9 107.43(17)
B O2 C8 107.44(17)
C5 N1 C1 117.84(16)
N1 C1 C2 122.45(18)
N1 C1 C6 115.93(17)
C2 C1 C6 121.62(18)
C3 C2 C1 120.33(18)
C2 C3 B 122.06(17)
C2 C3 C4 116.60(17)
C4 C3 B 121.35(17)
C3 C4 C5 120.54(18)
N1 C5 C4 122.24(18)
N1 C5 C7 116.16(17)
C4 C5 C7 121.60(18)
O2 C8 C9 103.9(6)
O2 C8 C10 110.6(12)
O2 C8 C11 103.7(14)
C9 C8 C11 110(2)
C10 C8 C9 118.1(19)
C10 C8 C11 109.6(8)
O1 C9 C8 103.8(6)
O1 C9 C12 102.7(16)
O1 C9 C13 110.9(14)
C8 C9 C12 110(2)
C13 C9 C8 118(2)
C13 C9 C12 109.8(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
B O1 1.364(3)
B O2 1.363(2)
B C3 1.567(3)
O1 C9 1.455(5)
O2 C8 1.452(4)
N1 C1 1.339(2)
N1 C5 1.337(2)
C1 C2 1.390(3)
C1 C6 1.504(3)
C2 C3 1.382(3)
C3 C4 1.384(3)
C4 C5 1.390(3)
C5 C7 1.506(3)
C8 C9 1.548(11)
C8 C10 1.489(18)
C8 C11 1.56(3)
C9 C12 1.57(4)
C9 C13 1.48(2)
