#------------------------------------------------------------------------------
#$Date: 2020-10-06 13:24:22 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257818 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/92/7059263.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_7059263
loop_
_publ_author_name
'Al-Zoubi, Raed M.'
'Al-Jammal, Walid K.'
'McDonald, Robert'
_publ_section_title
;
 Regioselective synthesis of ortho-iodobiphenylboronic acid derivatives: a
 superior catalyst for carboxylic acid activation
;
_journal_issue                   9
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              3612
_journal_page_last               3623
_journal_paper_doi               10.1039/C9NJ05708K
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety         'C12 H10 B I O2'
_chemical_formula_sum            'C12 H10 B I O2'
_chemical_formula_weight         323.91
_chemical_name_common            (5A)
_chemical_name_systematic        '(2-Iodobiphenyl-3-yl)boronic acid'
_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'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-11-28 deposited with the CCDC.	2020-01-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.619(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.9683(12)
_cell_length_b                   13.968(3)
_cell_length_c                   17.534(4)
_cell_measurement_reflns_used    2092
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      20.65
_cell_measurement_theta_min      2.74
_cell_volume                     1216.7(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            10367
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.427
_diffrn_reflns_theta_min         1.864
_exptl_absorpt_coefficient_mu    2.612
_exptl_absorpt_correction_T_max  0.9691
_exptl_absorpt_correction_T_min  0.6365
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.768
_exptl_crystal_description       fragment
_exptl_crystal_F_000             624
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethyl acetate / hexanes'
_exptl_crystal_size_max          0.268
_exptl_crystal_size_mid          0.076
_exptl_crystal_size_min          0.024
_refine_diff_density_max         0.712
_refine_diff_density_min         -0.581
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     153
_refine_ls_number_reflns         3014
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.990
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0361
_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)+(0.0314P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0695
_refine_ls_wR_factor_ref         0.0790
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2052
_reflns_number_total             3014
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9nj05708k2.cif
_cod_data_source_block           jus1502
_cod_depositor_comments
;Adding full bibliography for 7059263--7059266.cif.

 Adding full bibliography for 7059263--7059266.cif.
;
_cod_original_cell_volume        1216.8(5)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7059263
_shelx_shelxl_version_number     2014/7
_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. 
;
_shelx_estimated_absorpt_t_min   0.541
_shelx_estimated_absorpt_t_max   0.940
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
_atom_site_refinement_flags_adp
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 . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
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_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
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_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
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
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)
