# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_jus1502
_database_code_depnum_ccdc_archive 'CCDC 1881916'
loop_
_audit_author_name
_audit_author_address
'Robert McDonald'
;Department of Chemistry, University of Alberta
Canada
;
_audit_update_record             
;
2018-11-28 deposited with the CCDC.	2020-01-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '(2-Iodobiphenyl-3-yl)boronic acid'
_chemical_name_common            (5A)
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H10 B I O2'
_chemical_formula_sum            'C12 H10 B I O2'
_chemical_formula_weight         323.91

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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. 
;

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'

_cell_length_a                   4.9683(12)
_cell_length_b                   13.968(3)
_cell_length_c                   17.534(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.619(3)
_cell_angle_gamma                90
_cell_volume                     1216.8(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    2092
_cell_measurement_theta_min      2.74
_cell_measurement_theta_max      20.65

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.768
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.268
_exptl_crystal_size_mid          0.076
_exptl_crystal_size_min          0.024
_exptl_absorpt_coefficient_mu    2.612
_shelx_estimated_absorpt_T_min   0.541
_shelx_estimated_absorpt_T_max   0.940
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.6365
_exptl_absorpt_correction_T_max  0.9691
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10367
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.864
_diffrn_reflns_theta_max         28.427
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3014
_reflns_number_gt                2052
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0314P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3014
_refine_ls_number_parameters     153
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0361
_refine_ls_wR_factor_ref         0.0790
_refine_ls_wR_factor_gt          0.0695
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_restrained_S_all      0.990
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
I I 0.29538(6) 0.18552(2) 0.21803(2) 0.05336(12) Uani 1 1 d . . . . .
O1 O 0.2153(5) 0.0143(2) 0.07543(16) 0.0482(7) Uani 1 1 d D . . . .
H1O H 0.357(6) 0.009(3) 0.101(2) 0.090(18) Uiso 1 1 d D . . . .
O2 O -0.2468(5) -0.0022(2) 0.07963(16) 0.0498(7) Uani 1 1 d D . . . .
H2O H -0.223(10) 0.000(4) 0.0325(8) 0.10(2) Uiso 1 1 d D . . . .
C1 C 0.0750(7) 0.0516(2) 0.3382(2) 0.0380(8) Uani 1 1 d . . . . .
C2 C 0.0932(6) 0.0633(2) 0.25977(19) 0.0357(8) Uani 1 1 d . . . . .
C3 C -0.0182(6) -0.0018(2) 0.2075(2) 0.0364(8) Uani 1 1 d . . . . .
C4 C -0.1548(7) -0.0802(3) 0.2376(2) 0.0450(9) Uani 1 1 d . . . . .
H4 H -0.2416 -0.1238 0.2038 0.054 Uiso 1 1 calc R U . . .
C5 C -0.1668(8) -0.0959(3) 0.3146(2) 0.0508(10) Uani 1 1 d . . . . .
H5 H -0.2542 -0.1513 0.3338 0.061 Uiso 1 1 calc R U . . .
C6 C -0.0503(8) -0.0304(3) 0.3645(2) 0.0471(9) Uani 1 1 d . . . . .
H6 H -0.0566 -0.0421 0.4178 0.056 Uiso 1 1 calc R U . . .
C7 C 0.1707(7) 0.1225(2) 0.3958(2) 0.0406(8) Uani 1 1 d . . . . .
C8 C 0.0370(10) 0.2085(3) 0.4051(3) 0.0637(13) Uani 1 1 d . . . . .
H8 H -0.1114 0.2241 0.3729 0.076 Uiso 1 1 calc R U . . .
C9 C 0.1198(11) 0.2723(3) 0.4619(3) 0.0742(14) Uani 1 1 d . . . . .
H9 H 0.0270 0.3312 0.4680 0.089 Uiso 1 1 calc R U . . .
C10 C 0.3315(10) 0.2510(3) 0.5083(3) 0.0672(13) Uani 1 1 d . . . . .
H10 H 0.3871 0.2949 0.5467 0.081 Uiso 1 1 calc R U . . .
C11 C 0.4635(10) 0.1668(3) 0.4996(3) 0.0685(13) Uani 1 1 d . . . . .
H11 H 0.6115 0.1518 0.5322 0.082 Uiso 1 1 calc R U . . .
C12 C 0.3848(8) 0.1024(3) 0.4437(2) 0.0553(11) Uani 1 1 d . . . . .
H12 H 0.4796 0.0438 0.4382 0.066 Uiso 1 1 calc R U . . .
B B -0.0102(8) 0.0055(3) 0.1186(2) 0.0360(9) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I C2 2.115(3) . ?
O1 B 1.365(5) . ?
O1 H1O 0.830(10) . ?
O2 B 1.357(5) . ?
O2 H2O 0.836(10) . ?
C1 C6 1.385(5) . ?
C1 C2 1.389(5) . ?
C1 C7 1.488(5) . ?
C2 C3 1.401(5) . ?
C3 C4 1.396(5) . ?
C3 B 1.563(5) . ?
C4 C5 1.371(5) . ?
C5 C6 1.388(5) . ?
C7 C12 1.377(5) . ?
C7 C8 1.383(5) . ?
C8 C9 1.394(6) . ?
C9 C10 1.356(7) . ?
C10 C11 1.356(6) . ?
C11 C12 1.384(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
B O1 H1O 113(4) . . ?
B O2 H2O 111(4) . . ?
C6 C1 C2 117.5(3) . . ?
C6 C1 C7 117.7(3) . . ?
C2 C1 C7 124.7(3) . . ?
C1 C2 C3 122.8(3) . . ?
C1 C2 I 118.3(3) . . ?
C3 C2 I 118.9(2) . . ?
C4 C3 C2 116.9(3) . . ?
C4 C3 B 116.5(3) . . ?
C2 C3 B 126.6(3) . . ?
C5 C4 C3 121.7(3) . . ?
C4 C5 C6 119.5(4) . . ?
C1 C6 C5 121.5(4) . . ?
C12 C7 C8 118.2(4) . . ?
C12 C7 C1 121.2(3) . . ?
C8 C7 C1 120.5(3) . . ?
C7 C8 C9 120.1(4) . . ?
C10 C9 C8 120.6(4) . . ?
C11 C10 C9 119.7(4) . . ?
C10 C11 C12 120.6(4) . . ?
C7 C12 C11 120.7(4) . . ?
O2 B O1 116.1(3) . . ?
O2 B C3 117.7(3) . . ?
O1 B C3 126.1(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 2.6(5) . . . . ?
C7 C1 C2 C3 -174.9(3) . . . . ?
C6 C1 C2 I -177.9(3) . . . . ?
C7 C1 C2 I 4.6(4) . . . . ?
C1 C2 C3 C4 0.8(5) . . . . ?
I C2 C3 C4 -178.6(2) . . . . ?
C1 C2 C3 B 179.5(3) . . . . ?
I C2 C3 B 0.1(4) . . . . ?
C2 C3 C4 C5 -3.5(5) . . . . ?
B C3 C4 C5 177.6(3) . . . . ?
C3 C4 C5 C6 2.7(6) . . . . ?
C2 C1 C6 C5 -3.5(5) . . . . ?
C7 C1 C6 C5 174.2(3) . . . . ?
C4 C5 C6 C1 0.9(6) . . . . ?
C6 C1 C7 C12 69.5(5) . . . . ?
C2 C1 C7 C12 -113.0(4) . . . . ?
C6 C1 C7 C8 -107.1(4) . . . . ?
C2 C1 C7 C8 70.4(5) . . . . ?
C12 C7 C8 C9 0.0(7) . . . . ?
C1 C7 C8 C9 176.7(4) . . . . ?
C7 C8 C9 C10 0.1(8) . . . . ?
C8 C9 C10 C11 -0.2(8) . . . . ?
C9 C10 C11 C12 0.2(8) . . . . ?
C8 C7 C12 C11 0.1(6) . . . . ?
C1 C7 C12 C11 -176.7(4) . . . . ?
C10 C11 C12 C7 -0.1(7) . . . . ?
C4 C3 B O2 50.7(5) . . . . ?
C2 C3 B O2 -128.0(4) . . . . ?
C4 C3 B O1 -125.8(4) . . . . ?
C2 C3 B O1 55.5(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1O O2 0.830(10) 2.01(4) 2.683(3) 137(5) 1_655
O2 H2O O1 0.836(10) 1.904(14) 2.730(4) 170(5) 3

_refine_diff_density_max         0.712
_refine_diff_density_min         -0.581
_refine_diff_density_rms         0.089


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl acetate / hexanes'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_jus1508
_database_code_depnum_ccdc_archive 'CCDC 1881918'
loop_
_audit_author_name
_audit_author_address
'Robert McDonald'
;Department of Chemistry, University of Alberta
Canada
;
_audit_update_record             
;
2018-11-28 deposited with the CCDC.	2020-01-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
"(2-iodo-4',5-dimethoxybiphenyl-3-yl)boronic acid"
_chemical_name_common            (19A)
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H14 B I O4'
_chemical_formula_sum            'C14 H14 B I O4'
_chemical_formula_weight         383.96

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.4048(3)
_cell_length_b                   9.6801(4)
_cell_length_c                   10.5728(4)
_cell_angle_alpha                101.6750(4)
_cell_angle_beta                 90.6702(5)
_cell_angle_gamma                105.7630(4)
_cell_volume                     712.47(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    7784
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      28.07

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.790
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.168
_exptl_crystal_size_mid          0.139
_exptl_crystal_size_min          0.038
_exptl_absorpt_coefficient_mu    2.256
_shelx_estimated_absorpt_T_min   0.703
_shelx_estimated_absorpt_T_max   0.919
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7538
_exptl_absorpt_correction_T_max  0.9660
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6867
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_av_R_equivalents  0.0144
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.972
_diffrn_reflns_theta_max         28.344
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3500
_reflns_number_gt                3235
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'DIRDIF-2008 (Beurskens et al., 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0229P)²+0.3304P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3500
_refine_ls_number_parameters     191
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0232
_refine_ls_R_factor_gt           0.0208
_refine_ls_wR_factor_ref         0.0499
_refine_ls_wR_factor_gt          0.0485
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
I I 0.59205(2) 0.46716(2) 0.29533(2) 0.03040(5) Uani 1 1 d . . . . .
O1 O 1.0144(2) 0.39467(17) 0.13198(15) 0.0309(3) Uani 1 1 d D . . . .
H1O H 1.078(4) 0.463(2) 0.100(3) 0.059(9) Uiso 1 1 d D . . . .
O2 O 0.7784(2) 0.37270(16) -0.02707(14) 0.0272(3) Uani 1 1 d D . . . .
H2O H 0.672(2) 0.325(3) -0.061(3) 0.047(8) Uiso 1 1 d D . . . .
O3 O 0.58086(19) -0.19229(14) 0.12745(13) 0.0241(3) Uani 1 1 d . . . . .
O4 O -0.0925(2) 0.24448(16) 0.63368(14) 0.0284(3) Uani 1 1 d . . . . .
C1 C 0.4447(3) 0.1335(2) 0.27893(17) 0.0195(4) Uani 1 1 d . . . . .
C2 C 0.5718(3) 0.2419(2) 0.22811(17) 0.0195(4) Uani 1 1 d . . . . .
C3 C 0.7016(3) 0.2085(2) 0.14057(18) 0.0201(4) Uani 1 1 d . . . . .
C4 C 0.7085(3) 0.0626(2) 0.10565(18) 0.0207(4) Uani 1 1 d . . . . .
H4 H 0.7966 0.0377 0.0470 0.025 Uiso 1 1 calc R U . . .
C5 C 0.5866(3) -0.0458(2) 0.15679(17) 0.0198(4) Uani 1 1 d . . . . .
C6 C 0.4550(3) -0.0106(2) 0.24106(18) 0.0210(4) Uani 1 1 d . . . . .
H6 H 0.3705 -0.0863 0.2734 0.025 Uiso 1 1 calc R U . . .
C7 C 0.3010(3) 0.1641(2) 0.37029(18) 0.0203(4) Uani 1 1 d . . . . .
C8 C 0.1675(3) 0.2303(2) 0.33859(18) 0.0243(4) Uani 1 1 d . . . . .
H8 H 0.1684 0.2574 0.2571 0.029 Uiso 1 1 calc R U . . .
C9 C 0.0323(3) 0.2582(2) 0.42277(19) 0.0243(4) Uani 1 1 d . . . . .
H9 H -0.0583 0.3031 0.3987 0.029 Uiso 1 1 calc R U . . .
C10 C 0.0313(3) 0.2195(2) 0.54251(18) 0.0213(4) Uani 1 1 d . . . . .
C11 C 0.1613(3) 0.1503(2) 0.57504(18) 0.0236(4) Uani 1 1 d . . . . .
H11 H 0.1590 0.1220 0.6561 0.028 Uiso 1 1 calc R U . . .
C12 C 0.2942(3) 0.1224(2) 0.49017(18) 0.0217(4) Uani 1 1 d . . . . .
H12 H 0.3819 0.0744 0.5133 0.026 Uiso 1 1 calc R U . . .
C13 C 0.7291(3) -0.2329(2) 0.0558(2) 0.0304(4) Uani 1 1 d . . . . .
H13A H 0.8511 -0.1756 0.1007 0.036 Uiso 1 1 calc R U . . .
H13B H 0.7223 -0.2128 -0.0311 0.036 Uiso 1 1 calc R U . . .
H13C H 0.7149 -0.3378 0.0488 0.036 Uiso 1 1 calc R U . . .
C14 C -0.2118(3) 0.3307(3) 0.6094(2) 0.0330(5) Uani 1 1 d . . . . .
H14A H -0.2948 0.2795 0.5314 0.040 Uiso 1 1 calc R U . . .
H14B H -0.1349 0.4260 0.5966 0.040 Uiso 1 1 calc R U . . .
H14C H -0.2879 0.3460 0.6834 0.040 Uiso 1 1 calc R U . . .
B B 0.8383(3) 0.3329(2) 0.0798(2) 0.0219(4) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I C2 2.1157(18) . ?
O1 B 1.337(3) . ?
O2 B 1.371(3) . ?
O3 C5 1.378(2) . ?
O3 C13 1.437(2) . ?
O4 C10 1.369(2) . ?
O4 C14 1.423(2) . ?
C1 C6 1.395(3) . ?
C1 C2 1.407(2) . ?
C1 C7 1.494(3) . ?
C2 C3 1.398(3) . ?
C3 C4 1.401(3) . ?
C3 B 1.598(3) . ?
C4 C5 1.391(2) . ?
C5 C6 1.392(3) . ?
C7 C8 1.386(3) . ?
C7 C12 1.403(3) . ?
C8 C9 1.392(3) . ?
C9 C10 1.390(3) . ?
C10 C11 1.390(3) . ?
C11 C12 1.383(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O3 C13 117.85(15) . . ?
C10 O4 C14 117.06(16) . . ?
C6 C1 C2 117.43(17) . . ?
C6 C1 C7 118.66(16) . . ?
C2 C1 C7 123.91(17) . . ?
C3 C2 C1 122.26(17) . . ?
C3 C2 I 116.64(13) . . ?
C1 C2 I 120.85(13) . . ?
C2 C3 C4 118.57(16) . . ?
C2 C3 B 121.14(16) . . ?
C4 C3 B 120.29(16) . . ?
C5 C4 C3 120.07(17) . . ?
O3 C5 C4 124.49(17) . . ?
O3 C5 C6 115.15(16) . . ?
C4 C5 C6 120.34(17) . . ?
C5 C6 C1 121.28(17) . . ?
C8 C7 C12 117.91(17) . . ?
C8 C7 C1 121.55(16) . . ?
C12 C7 C1 120.51(16) . . ?
C7 C8 C9 121.91(17) . . ?
C10 C9 C8 119.22(18) . . ?
O4 C10 C11 116.09(17) . . ?
O4 C10 C9 124.15(17) . . ?
C11 C10 C9 119.76(17) . . ?
C12 C11 C10 120.41(17) . . ?
C11 C12 C7 120.75(17) . . ?
O1 B O2 120.18(18) . . ?
O1 B C3 119.14(17) . . ?
O2 B C3 120.65(17) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 1.5(3) . . . . ?
C7 C1 C2 C3 -178.55(17) . . . . ?
C6 C1 C2 I -172.62(13) . . . . ?
C7 C1 C2 I 7.4(2) . . . . ?
C1 C2 C3 C4 -2.0(3) . . . . ?
I C2 C3 C4 172.36(13) . . . . ?
C1 C2 C3 B 177.33(17) . . . . ?
I C2 C3 B -8.3(2) . . . . ?
C2 C3 C4 C5 0.6(3) . . . . ?
B C3 C4 C5 -178.66(17) . . . . ?
C13 O3 C5 C4 10.3(3) . . . . ?
C13 O3 C5 C6 -171.52(17) . . . . ?
C3 C4 C5 O3 179.24(17) . . . . ?
C3 C4 C5 C6 1.1(3) . . . . ?
O3 C5 C6 C1 -179.92(16) . . . . ?
C4 C5 C6 C1 -1.6(3) . . . . ?
C2 C1 C6 C5 0.3(3) . . . . ?
C7 C1 C6 C5 -179.63(17) . . . . ?
C6 C1 C7 C8 -122.8(2) . . . . ?
C2 C1 C7 C8 57.2(3) . . . . ?
C6 C1 C7 C12 55.3(2) . . . . ?
C2 C1 C7 C12 -124.6(2) . . . . ?
C12 C7 C8 C9 1.3(3) . . . . ?
C1 C7 C8 C9 179.51(18) . . . . ?
C7 C8 C9 C10 0.4(3) . . . . ?
C14 O4 C10 C11 172.62(18) . . . . ?
C14 O4 C10 C9 -7.7(3) . . . . ?
C8 C9 C10 O4 178.62(18) . . . . ?
C8 C9 C10 C11 -1.7(3) . . . . ?
O4 C10 C11 C12 -178.98(18) . . . . ?
C9 C10 C11 C12 1.4(3) . . . . ?
C10 C11 C12 C7 0.4(3) . . . . ?
C8 C7 C12 C11 -1.7(3) . . . . ?
C1 C7 C12 C11 -179.94(17) . . . . ?
C2 C3 B O1 97.9(2) . . . . ?
C4 C3 B O1 -82.8(2) . . . . ?
C2 C3 B O2 -84.2(2) . . . . ?
C4 C3 B O2 95.1(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1O O2 0.832(10) 1.966(10) 2.7979(19) 178(3) 2_765
O2 H2O O3 0.832(10) 1.987(11) 2.813(2) 172(3) 2_655

_refine_diff_density_max         0.924
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.071


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexanes'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_jus1511
_database_code_depnum_ccdc_archive 'CCDC 1881917'
loop_
_audit_author_name
_audit_author_address
'Robert McDonald'
;Department of Chemistry, University of Alberta
Canada
;
_audit_update_record             
;
2018-11-28 deposited with the CCDC.	2020-01-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '(2-iodo-5-methoxybiphenyl-3-yl)boronic acid'
_chemical_name_common            (14A)
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H12 B I O3'
_chemical_formula_sum            'C13 H12 B I O3'
_chemical_formula_weight         353.94

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 2/a'
_space_group_name_Hall           '-I 2ya'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   19.7878(14)
_cell_length_b                   5.0588(4)
_cell_length_c                   27.336(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.9416(10)
_cell_angle_gamma                90
_cell_volume                     2729.9(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    8347
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      27.56

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.722
_exptl_crystal_F_000             1376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.562
_exptl_crystal_size_mid          0.063
_exptl_crystal_size_min          0.033
_exptl_absorpt_coefficient_mu    2.342
_shelx_estimated_absorpt_T_min   0.353
_shelx_estimated_absorpt_T_max   0.927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6605
_exptl_absorpt_correction_T_max  0.7967
_exptl_absorpt_process_details   'TWINABS (Sheldrick, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22880
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         1.493
_diffrn_reflns_theta_max         27.571
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3157
_reflns_number_gt                2747
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'DIRDIF-2008 (Beurskens et al., 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          'Refined as a 2-component twin.,Twin'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0303P)²+4.1548P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3157
_refine_ls_number_parameters     173
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0264
_refine_ls_wR_factor_ref         0.0625
_refine_ls_wR_factor_gt          0.0592
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
I I 0.02560(2) 0.63092(4) 0.20447(2) 0.02817(7) Uani 1 1 d . . . . .
O1 O 0.19356(12) 0.4661(4) 0.21985(10) 0.0357(6) Uani 1 1 d D . . . .
H1O H 0.181(2) 0.610(5) 0.2080(16) 0.063(15) Uiso 1 1 d D . . . .
O2 O 0.19887(13) 0.0117(5) 0.21119(10) 0.0404(6) Uani 1 1 d D . . . .
H2O H 0.2283(17) 0.026(9) 0.2345(11) 0.065(15) Uiso 1 1 d D . . . .
O3 O 0.09875(13) -0.1070(5) 0.03209(9) 0.0425(6) Uani 1 1 d . . . . .
C1 C 0.00555(16) 0.3339(6) 0.10785(11) 0.0264(6) Uani 1 1 d . . . . .
C2 C 0.05223(15) 0.3677(5) 0.14882(11) 0.0236(6) Uani 1 1 d . . . . .
C3 C 0.11399(15) 0.2328(6) 0.15281(11) 0.0228(6) Uani 1 1 d . . . . .
C4 C 0.12944(15) 0.0651(6) 0.11418(12) 0.0265(6) Uani 1 1 d . . . . .
H4 H 0.1701 -0.0354 0.1168 0.032 Uiso 1 1 calc R U . . .
C5 C 0.08609(16) 0.0442(6) 0.07214(12) 0.0294(7) Uani 1 1 d . . . . .
C6 C 0.02471(16) 0.1790(6) 0.06936(12) 0.0305(7) Uani 1 1 d . . . . .
H6 H -0.0047 0.1645 0.0405 0.037 Uiso 1 1 calc R U . . .
C7 C -0.06452(16) 0.4419(7) 0.10540(12) 0.0314(7) Uani 1 1 d . . . . .
C8 C -0.1113(2) 0.3375(8) 0.13557(16) 0.0482(10) Uani 1 1 d . . . . .
H8 H -0.0979 0.2011 0.1581 0.058 Uiso 1 1 calc R U . . .
C9 C -0.1774(2) 0.4298(11) 0.1333(2) 0.0665(14) Uani 1 1 d . . . . .
H9 H -0.2093 0.3557 0.1537 0.080 Uiso 1 1 calc R U . . .
C10 C -0.1961(2) 0.6293(10) 0.1011(2) 0.0664(15) Uani 1 1 d . . . . .
H10 H -0.2411 0.6956 0.0999 0.080 Uiso 1 1 calc R U . . .
C11 C -0.1508(2) 0.7343(9) 0.07061(19) 0.0600(13) Uani 1 1 d . . . . .
H11 H -0.1643 0.8722 0.0485 0.072 Uiso 1 1 calc R U . . .
C12 C -0.08481(19) 0.6378(7) 0.07230(15) 0.0417(9) Uani 1 1 d . . . . .
H12 H -0.0536 0.7066 0.0506 0.050 Uiso 1 1 calc R U . . .
C13 C 0.1575(2) -0.2689(9) 0.03591(16) 0.0515(11) Uani 1 1 d . . . . .
H13A H 0.1979 -0.1575 0.0412 0.062 Uiso 1 1 calc R U . . .
H13B H 0.1603 -0.3702 0.0056 0.062 Uiso 1 1 calc R U . . .
H13C H 0.1549 -0.3909 0.0636 0.062 Uiso 1 1 calc R U . . .
B B 0.16917(18) 0.2426(7) 0.19709(13) 0.0268(7) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I C2 2.116(3) . ?
O1 B 1.363(4) . ?
O2 B 1.352(4) . ?
O3 C5 1.373(4) . ?
O3 C13 1.420(4) . ?
C1 C6 1.386(4) . ?
C1 C2 1.412(4) . ?
C1 C7 1.488(4) . ?
C2 C3 1.397(4) . ?
C3 C4 1.404(4) . ?
C3 B 1.574(4) . ?
C4 C5 1.390(4) . ?
C5 C6 1.390(5) . ?
C7 C12 1.383(5) . ?
C7 C8 1.386(5) . ?
C8 C9 1.385(6) . ?
C9 C10 1.373(7) . ?
C10 C11 1.373(7) . ?
C11 C12 1.391(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O3 C13 117.1(3) . . ?
C6 C1 C2 118.2(3) . . ?
C6 C1 C7 118.4(3) . . ?
C2 C1 C7 123.2(3) . . ?
C3 C2 C1 121.6(3) . . ?
C3 C2 I 120.7(2) . . ?
C1 C2 I 117.7(2) . . ?
C2 C3 C4 118.1(3) . . ?
C2 C3 B 127.0(3) . . ?
C4 C3 B 115.0(3) . . ?
C5 C4 C3 120.9(3) . . ?
O3 C5 C4 124.5(3) . . ?
O3 C5 C6 115.9(3) . . ?
C4 C5 C6 119.7(3) . . ?
C1 C6 C5 121.3(3) . . ?
C12 C7 C8 119.1(3) . . ?
C12 C7 C1 121.4(3) . . ?
C8 C7 C1 119.5(3) . . ?
C9 C8 C7 120.8(4) . . ?
C10 C9 C8 119.3(5) . . ?
C9 C10 C11 120.9(4) . . ?
C10 C11 C12 119.7(4) . . ?
C7 C12 C11 120.2(4) . . ?
O2 B O1 117.0(3) . . ?
O2 B C3 117.2(3) . . ?
O1 B C3 125.6(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -5.2(4) . . . . ?
C7 C1 C2 C3 170.8(3) . . . . ?
C6 C1 C2 I 174.8(2) . . . . ?
C7 C1 C2 I -9.2(4) . . . . ?
C1 C2 C3 C4 1.4(4) . . . . ?
I C2 C3 C4 -178.6(2) . . . . ?
C1 C2 C3 B -177.4(3) . . . . ?
I C2 C3 B 2.6(4) . . . . ?
C2 C3 C4 C5 3.2(5) . . . . ?
B C3 C4 C5 -178.0(3) . . . . ?
C13 O3 C5 C4 5.5(5) . . . . ?
C13 O3 C5 C6 -173.4(3) . . . . ?
C3 C4 C5 O3 177.4(3) . . . . ?
C3 C4 C5 C6 -3.8(5) . . . . ?
C2 C1 C6 C5 4.6(5) . . . . ?
C7 C1 C6 C5 -171.6(3) . . . . ?
O3 C5 C6 C1 178.7(3) . . . . ?
C4 C5 C6 C1 -0.2(5) . . . . ?
C6 C1 C7 C12 -70.0(4) . . . . ?
C2 C1 C7 C12 114.1(4) . . . . ?
C6 C1 C7 C8 107.5(4) . . . . ?
C2 C1 C7 C8 -68.4(4) . . . . ?
C12 C7 C8 C9 -0.9(6) . . . . ?
C1 C7 C8 C9 -178.5(4) . . . . ?
C7 C8 C9 C10 -0.8(7) . . . . ?
C8 C9 C10 C11 1.3(7) . . . . ?
C9 C10 C11 C12 -0.1(7) . . . . ?
C8 C7 C12 C11 2.2(6) . . . . ?
C1 C7 C12 C11 179.7(3) . . . . ?
C10 C11 C12 C7 -1.7(6) . . . . ?
C2 C3 B O2 138.2(3) . . . . ?
C4 C3 B O2 -40.5(4) . . . . ?
C2 C3 B O1 -47.4(5) . . . . ?
C4 C3 B O1 133.8(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1O O2 0.830(10) 2.06(3) 2.773(3) 143(4) 1_565
O2 H2O O1 0.836(10) 1.920(13) 2.747(3) 170(5) 7

_refine_diff_density_max         0.976
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.096


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane / Hexanes'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_jus1509
_database_code_depnum_ccdc_archive 'CCDC 1881919'
loop_
_audit_author_name
_audit_author_address
'Robert McDonald'
;Department of Chemistry, University of Alberta
Canada
;
_audit_update_record             
;
2018-11-28 deposited with the CCDC.	2020-01-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
"(2-iodo-5-methoxy-4'-phenoxybiphenyl-3-yl)boronic acid"
_chemical_name_common            (21A)
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H16 B I O4'
_chemical_formula_sum            'C19 H16 B I O4'
_chemical_formula_weight         446.03

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.1433(2)
_cell_length_b                   13.2175(4)
_cell_length_c                   14.1071(4)
_cell_angle_alpha                114.1398(17)
_cell_angle_beta                 94.4519(16)
_cell_angle_gamma                93.3392(16)
_cell_volume                     868.24(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9848
_cell_measurement_theta_min      3.45
_cell_measurement_theta_max      73.67

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.706
_exptl_crystal_F_000             440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.214
_exptl_crystal_size_mid          0.046
_exptl_crystal_size_min          0.021
_exptl_absorpt_coefficient_mu    14.668
_shelx_estimated_absorpt_T_min   0.145
_shelx_estimated_absorpt_T_max   0.748
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.2320
_exptl_absorpt_correction_T_max  0.8683
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6177
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.455
_diffrn_reflns_theta_max         73.947
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measured_fraction_theta_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_point_group_measured_fraction_full 0.967
_reflns_number_total             3396
_reflns_number_gt                3147
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0309P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3396
_refine_ls_number_parameters     235
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0270
_refine_ls_R_factor_gt           0.0252
_refine_ls_wR_factor_ref         0.0610
_refine_ls_wR_factor_gt          0.0605
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_restrained_S_all      0.997
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
I I 0.09245(3) 0.63235(2) 0.45180(2) 0.02620(7) Uani 1 1 d . . . . .
O1 O 0.2300(4) 0.87928(15) 0.42428(18) 0.0298(4) Uani 1 1 d D . . . .
H1O H 0.263(8) 0.9469(12) 0.464(3) 0.046(12) Uiso 1 1 d D . . . .
O2 O 0.6861(4) 0.89361(16) 0.45499(18) 0.0314(4) Uani 1 1 d D . . . .
H2O H 0.826(4) 0.864(3) 0.453(3) 0.039(10) Uiso 1 1 d D . . . .
O3 O 0.7652(4) 0.55925(17) 0.08337(17) 0.0317(4) Uani 1 1 d . . . . .
O4 O -0.0433(5) 0.11239(19) 0.28855(18) 0.0393(5) Uani 1 1 d . . . . .
C1 C 0.3394(5) 0.5041(2) 0.2529(2) 0.0206(5) Uani 1 1 d . . . . .
C2 C 0.3217(5) 0.6120(2) 0.32880(19) 0.0192(4) Uani 1 1 d . . . . .
C3 C 0.4588(5) 0.7050(2) 0.3255(2) 0.0206(5) Uani 1 1 d . . . . .
C4 C 0.6144(5) 0.6887(2) 0.2445(2) 0.0225(5) Uani 1 1 d . . . . .
H4 H 0.7156 0.7504 0.2431 0.027 Uiso 1 1 calc R U . . .
C5 C 0.6226(5) 0.5830(2) 0.1660(2) 0.0235(5) Uani 1 1 d . . . . .
C6 C 0.4822(5) 0.4919(2) 0.1702(2) 0.0233(5) Uani 1 1 d . . . . .
H6 H 0.4844 0.4201 0.1153 0.028 Uiso 1 1 calc R U . . .
C7 C 0.2276(5) 0.4013(2) 0.2606(2) 0.0224(5) Uani 1 1 d . . . . .
C8 C 0.0030(6) 0.3386(2) 0.1989(2) 0.0295(6) Uani 1 1 d . . . . .
H8 H -0.0868 0.3625 0.1515 0.035 Uiso 1 1 calc R U . . .
C9 C -0.0935(6) 0.2411(2) 0.2055(3) 0.0337(7) Uani 1 1 d . . . . .
H9 H -0.2502 0.1999 0.1641 0.040 Uiso 1 1 calc R U . . .
C10 C 0.0414(6) 0.2051(2) 0.2727(2) 0.0268(5) Uani 1 1 d . . . . .
C11 C 0.2685(6) 0.2656(2) 0.3341(2) 0.0295(6) Uani 1 1 d . . . . .
H11 H 0.3613 0.2401 0.3796 0.035 Uiso 1 1 calc R U . . .
C12 C 0.3594(6) 0.3639(2) 0.3287(2) 0.0284(6) Uani 1 1 d . . . . .
H12 H 0.5130 0.4063 0.3718 0.034 Uiso 1 1 calc R U . . .
C13 C 0.9483(6) 0.6463(2) 0.0858(2) 0.0314(6) Uani 1 1 d . . . . .
H13A H 0.8529 0.7056 0.0792 0.038 Uiso 1 1 calc R U . . .
H13B H 1.0551 0.6163 0.0276 0.038 Uiso 1 1 calc R U . . .
H13C H 1.0622 0.6767 0.1521 0.038 Uiso 1 1 calc R U . . .
C14 C -0.2206(6) 0.0305(2) 0.2142(2) 0.0302(6) Uani 1 1 d . . . . .
C15 C -0.4343(6) -0.0062(3) 0.2498(3) 0.0338(6) Uani 1 1 d . . . . .
H15 H -0.4619 0.0283 0.3215 0.041 Uiso 1 1 calc R U . . .
C16 C -0.6078(7) -0.0940(3) 0.1794(3) 0.0402(8) Uani 1 1 d . . . . .
H16 H -0.7542 -0.1202 0.2030 0.048 Uiso 1 1 calc R U . . .
C17 C -0.5682(7) -0.1433(3) 0.0750(3) 0.0426(8) Uani 1 1 d . . . . .
H17 H -0.6887 -0.2027 0.0269 0.051 Uiso 1 1 calc R U . . .
C18 C -0.3535(7) -0.1063(3) 0.0406(3) 0.0385(7) Uani 1 1 d . . . . .
H18 H -0.3263 -0.1407 -0.0311 0.046 Uiso 1 1 calc R U . . .
C19 C -0.1773(6) -0.0191(3) 0.1102(3) 0.0344(6) Uani 1 1 d . . . . .
H19 H -0.0291 0.0062 0.0867 0.041 Uiso 1 1 calc R U . . .
B B 0.4553(6) 0.8303(2) 0.4069(2) 0.0213(5) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I C2 2.109(3) . ?
O1 B 1.350(4) . ?
O2 B 1.365(3) . ?
O3 C5 1.362(3) . ?
O3 C13 1.432(3) . ?
O4 C14 1.382(3) . ?
O4 C10 1.384(3) . ?
C1 C6 1.386(4) . ?
C1 C2 1.404(3) . ?
C1 C7 1.492(3) . ?
C2 C3 1.401(3) . ?
C3 C4 1.398(4) . ?
C3 B 1.585(4) . ?
C4 C5 1.388(4) . ?
C5 C6 1.393(4) . ?
C7 C8 1.386(3) . ?
C7 C12 1.397(4) . ?
C8 C9 1.395(4) . ?
C9 C10 1.384(4) . ?
C10 C11 1.387(4) . ?
C11 C12 1.389(4) . ?
C14 C19 1.383(5) . ?
C14 C15 1.385(4) . ?
C15 C16 1.389(4) . ?
C16 C17 1.382(6) . ?
C17 C18 1.382(5) . ?
C18 C19 1.389(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O3 C13 117.3(2) . . ?
C14 O4 C10 119.8(2) . . ?
C6 C1 C2 118.4(2) . . ?
C6 C1 C7 118.2(2) . . ?
C2 C1 C7 123.3(2) . . ?
C3 C2 C1 121.2(2) . . ?
C3 C2 I 119.96(19) . . ?
C1 C2 I 118.83(18) . . ?
C4 C3 C2 118.7(2) . . ?
C4 C3 B 115.7(2) . . ?
C2 C3 B 125.7(2) . . ?
C5 C4 C3 120.7(2) . . ?
O3 C5 C4 124.8(2) . . ?
O3 C5 C6 115.5(2) . . ?
C4 C5 C6 119.6(3) . . ?
C1 C6 C5 121.2(2) . . ?
C8 C7 C12 118.7(2) . . ?
C8 C7 C1 122.1(2) . . ?
C12 C7 C1 119.1(2) . . ?
C7 C8 C9 121.1(3) . . ?
C10 C9 C8 119.3(3) . . ?
C9 C10 O4 123.9(3) . . ?
C9 C10 C11 120.6(2) . . ?
O4 C10 C11 115.4(2) . . ?
C10 C11 C12 119.6(2) . . ?
C11 C12 C7 120.8(2) . . ?
O4 C14 C19 121.8(3) . . ?
O4 C14 C15 116.9(3) . . ?
C19 C14 C15 121.1(3) . . ?
C14 C15 C16 119.1(3) . . ?
C17 C16 C15 120.3(3) . . ?
C18 C17 C16 120.0(3) . . ?
C17 C18 C19 120.4(3) . . ?
C14 C19 C18 119.1(3) . . ?
O1 B O2 118.5(2) . . ?
O1 B C3 121.6(2) . . ?
O2 B C3 119.7(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -4.3(4) . . . . ?
C7 C1 C2 C3 171.4(2) . . . . ?
C6 C1 C2 I 177.53(18) . . . . ?
C7 C1 C2 I -6.8(3) . . . . ?
C1 C2 C3 C4 0.2(4) . . . . ?
I C2 C3 C4 178.40(18) . . . . ?
C1 C2 C3 B -179.6(2) . . . . ?
I C2 C3 B -1.4(3) . . . . ?
C2 C3 C4 C5 3.2(4) . . . . ?
B C3 C4 C5 -176.9(2) . . . . ?
C13 O3 C5 C4 9.5(4) . . . . ?
C13 O3 C5 C6 -169.0(2) . . . . ?
C3 C4 C5 O3 179.1(2) . . . . ?
C3 C4 C5 C6 -2.5(4) . . . . ?
C2 C1 C6 C5 5.0(4) . . . . ?
C7 C1 C6 C5 -170.9(2) . . . . ?
O3 C5 C6 C1 176.8(2) . . . . ?
C4 C5 C6 C1 -1.7(4) . . . . ?
C6 C1 C7 C8 -78.0(4) . . . . ?
C2 C1 C7 C8 106.3(3) . . . . ?
C6 C1 C7 C12 99.2(3) . . . . ?
C2 C1 C7 C12 -76.5(4) . . . . ?
C12 C7 C8 C9 1.0(5) . . . . ?
C1 C7 C8 C9 178.2(3) . . . . ?
C7 C8 C9 C10 -1.6(5) . . . . ?
C8 C9 C10 O4 177.0(3) . . . . ?
C8 C9 C10 C11 0.8(5) . . . . ?
C14 O4 C10 C9 21.2(5) . . . . ?
C14 O4 C10 C11 -162.4(3) . . . . ?
C9 C10 C11 C12 0.7(5) . . . . ?
O4 C10 C11 C12 -175.9(3) . . . . ?
C10 C11 C12 C7 -1.3(5) . . . . ?
C8 C7 C12 C11 0.5(5) . . . . ?
C1 C7 C12 C11 -176.8(3) . . . . ?
C10 O4 C14 C19 52.8(4) . . . . ?
C10 O4 C14 C15 -132.1(3) . . . . ?
O4 C14 C15 C16 -175.3(3) . . . . ?
C19 C14 C15 C16 -0.2(5) . . . . ?
C14 C15 C16 C17 -0.5(5) . . . . ?
C15 C16 C17 C18 0.8(5) . . . . ?
C16 C17 C18 C19 -0.4(5) . . . . ?
O4 C14 C19 C18 175.5(3) . . . . ?
C15 C14 C19 C18 0.6(5) . . . . ?
C17 C18 C19 C14 -0.3(5) . . . . ?
C4 C3 B O1 121.5(3) . . . . ?
C2 C3 B O1 -58.6(4) . . . . ?
C4 C3 B O2 -53.3(3) . . . . ?
C2 C3 B O2 126.6(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1O O2 0.835(10) 1.934(11) 2.766(3) 174(4) 2_676
O2 H2O O1 0.836(10) 2.16(3) 2.869(3) 143(4) 1_655

_refine_diff_density_max         0.799
_refine_diff_density_min         -0.713
_refine_diff_density_rms         0.085


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexanes'
