#------------------------------------------------------------------------------
#$Date: 2020-10-06 13:24:22 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257818 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/92/7059266.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_7059266
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         'C19 H16 B I O4'
_chemical_formula_sum            'C19 H16 B I O4'
_chemical_formula_weight         446.03
_chemical_name_common            (21A)
_chemical_name_systematic
'(2-iodo-5-methoxy-4'-phenoxybiphenyl-3-yl)boronic acid'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -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                114.1398(17)
_cell_angle_beta                 94.4519(16)
_cell_angle_gamma                93.3392(16)
_cell_formula_units_Z            2
_cell_length_a                   5.1433(2)
_cell_length_b                   13.2175(4)
_cell_length_c                   14.1071(4)
_cell_measurement_reflns_used    9848
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      73.67
_cell_measurement_theta_min      3.45
_cell_volume                     868.24(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, 2015)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6177
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         73.947
_diffrn_reflns_theta_min         3.455
_exptl_absorpt_coefficient_mu    14.668
_exptl_absorpt_correction_T_max  0.8683
_exptl_absorpt_correction_T_min  0.2320
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.706
_exptl_crystal_description       rod
_exptl_crystal_F_000             440
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Hexanes'
_exptl_crystal_size_max          0.214
_exptl_crystal_size_mid          0.046
_exptl_crystal_size_min          0.021
_refine_diff_density_max         0.799
_refine_diff_density_min         -0.713
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3396
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.0270
_refine_ls_R_factor_gt           0.0252
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0309P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0605
_refine_ls_wR_factor_ref         0.0610
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3147
_reflns_number_total             3396
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9nj05708k2.cif
_cod_data_source_block           jus1509
_cod_depositor_comments
;Adding full bibliography for 7059263--7059266.cif.

 Adding full bibliography for 7059263--7059266.cif.
;
_cod_database_code               7059266
_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   0.145
_shelx_estimated_absorpt_t_max   0.748
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
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 . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
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_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
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_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
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 -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)
