#------------------------------------------------------------------------------
#$Date: 2025-08-22 00:26:11 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301853 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/43/7104330.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_7104330
loop_
_publ_author_name
'Zhang, Lu'
'Kerszulis, Justin A'
'Clark, Ronald J'
'Ye, Tao'
'Zhu, Lei'
_publ_section_title
;
 Catechol boronate formation and its electrochemical oxidation.
;
_journal_issue                   16
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2151
_journal_page_last               2153
_journal_paper_doi               10.1039/b900016j
_journal_volume                  34
_journal_year                    2009
_chemical_formula_moiety         'C23 H22 B N O2'
_chemical_formula_sum            'C23 H22 B N O2'
_chemical_formula_weight         355.23
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.544(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.8636(13)
_cell_length_b                   12.4780(16)
_cell_length_c                   15.734(2)
_cell_measurement_reflns_used    6589
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      28.57
_cell_measurement_theta_min      2.29
_cell_volume                     1915.0(4)
_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-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.947
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_sigmaI/netI    0.0232
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            22109
_diffrn_reflns_theta_full        29.01
_diffrn_reflns_theta_max         29.01
_diffrn_reflns_theta_min         2.09
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.9939
_exptl_absorpt_correction_T_min  0.9302
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       thin
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         4833
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0391
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0478P)²+0.5218P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.1049
_reflns_number_gt                3868
_reflns_number_total             4833
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b900016j.txt
_cod_data_source_block           zhu19
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_Hall     -P2yn
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7104330
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.84061(11) 0.70328(9) -0.09332(8) 0.0269(2) Uani 1 1 d . . .
H1 H 0.8581 0.7348 -0.1456 0.032 Uiso 1 1 calc R . .
C2 C 0.81746(12) 0.76720(9) -0.02740(8) 0.0306(3) Uani 1 1 d . . .
H2 H 0.8183 0.8429 -0.0338 0.037 Uiso 1 1 calc R . .
C3 C 0.79193(12) 0.72141(9) 0.05110(8) 0.0289(3) Uani 1 1 d . . .
H3 H 0.7751 0.7669 0.0968 0.035 Uiso 1 1 calc R . .
C4 C 0.79118(11) 0.61315(9) 0.06189(7) 0.0241(2) Uani 1 1 d . . .
H4 H 0.7743 0.5846 0.1153 0.029 Uiso 1 1 calc R . .
C5 C 0.81526(10) 0.54123(8) -0.00540(7) 0.0203(2) Uani 1 1 d . . .
C6 C 0.83915(10) 0.58877(9) -0.08545(7) 0.0220(2) Uani 1 1 d . . .
C7 C 0.86093(11) 0.52344(9) -0.15388(7) 0.0242(2) Uani 1 1 d . . .
H7 H 0.8772 0.5554 -0.2062 0.029 Uiso 1 1 calc R . .
C8 C 0.85940(11) 0.41195(9) -0.14723(7) 0.0231(2) Uani 1 1 d . . .
C9 C 0.87774(12) 0.34452(10) -0.21806(8) 0.0288(3) Uani 1 1 d . . .
H9 H 0.8919 0.3761 -0.2710 0.035 Uiso 1 1 calc R . .
C10 C 0.87531(12) 0.23618(10) -0.21097(8) 0.0318(3) Uani 1 1 d . . .
H10 H 0.8863 0.1927 -0.2591 0.038 Uiso 1 1 calc R . .
C11 C 0.85654(12) 0.18767(10) -0.13225(8) 0.0304(3) Uani 1 1 d . . .
H11 H 0.8555 0.1118 -0.1278 0.036 Uiso 1 1 calc R . .
C12 C 0.83991(11) 0.24890(9) -0.06279(8) 0.0252(2) Uani 1 1 d . . .
H12 H 0.8291 0.2148 -0.0102 0.030 Uiso 1 1 calc R . .
C13 C 0.83843(10) 0.36346(8) -0.06743(7) 0.0210(2) Uani 1 1 d . . .
C14 C 0.81655(10) 0.42832(8) 0.00286(7) 0.0197(2) Uani 1 1 d . . .
C15 C 0.80223(11) 0.37521(9) 0.08721(7) 0.0210(2) Uani 1 1 d . . .
H15A H 0.8778(13) 0.3233(10) 0.1017(8) 0.025 Uiso 1 1 d . . .
H15B H 0.8153(13) 0.4288(11) 0.1356(8) 0.025 Uiso 1 1 d . . .
N1 N 0.67233(9) 0.31583(7) 0.08840(6) 0.02004(19) Uani 1 1 d . . .
C17 C 0.55215(11) 0.38476(9) 0.06326(8) 0.0279(3) Uani 1 1 d . . .
H17A H 0.5564 0.4465 0.1021 0.042 Uiso 1 1 calc R . .
H17B H 0.4683 0.3438 0.0667 0.042 Uiso 1 1 calc R . .
H17C H 0.5516 0.4099 0.0042 0.042 Uiso 1 1 calc R . .
C18 C 0.67034(11) 0.27375(9) 0.17624(7) 0.0230(2) Uani 1 1 d . . .
H18A H 0.5809 0.2389 0.1790 0.028 Uiso 1 1 calc R . .
H18B H 0.6805 0.3339 0.2177 0.028 Uiso 1 1 calc R . .
C19 C 0.78425(11) 0.19372(8) 0.20120(7) 0.0209(2) Uani 1 1 d . . .
C20 C 0.89473(12) 0.22272(9) 0.26287(7) 0.0248(2) Uani 1 1 d . . .
H20 H 0.8945 0.2905 0.2903 0.030 Uiso 1 1 calc R . .
C21 C 1.00506(12) 0.15383(10) 0.28473(8) 0.0292(3) Uani 1 1 d . . .
H21 H 1.0800 0.1746 0.3266 0.035 Uiso 1 1 calc R . .
C22 C 1.00507(12) 0.05480(10) 0.24510(8) 0.0313(3) Uani 1 1 d . . .
H22 H 1.0812 0.0080 0.2586 0.038 Uiso 1 1 calc R . .
C23 C 0.89366(12) 0.02395(9) 0.18554(8) 0.0281(3) Uani 1 1 d . . .
H23 H 0.8937 -0.0451 0.1601 0.034 Uiso 1 1 calc R . .
C24 C 0.78113(11) 0.09185(9) 0.16183(7) 0.0227(2) Uani 1 1 d . . .
B1 B 0.65874(13) 0.05077(10) 0.09288(9) 0.0245(3) Uani 1 1 d . . .
O1 O 0.62856(10) -0.05525(7) 0.09294(6) 0.0347(2) Uani 1 1 d . . .
H1O H 0.5595(16) -0.0757(13) 0.0536(10) 0.042 Uiso 1 1 d . . .
O2 O 0.58613(8) 0.11717(6) 0.03387(5) 0.0284(2) Uani 1 1 d . . .
H2O H 0.6178(15) 0.1850(12) 0.0412(9) 0.034 Uiso 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 121.04(11) . . ?
C2 C1 H1 119.5 . . ?
C6 C1 H1 119.5 . . ?
C1 C2 C3 120.13(11) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C4 C3 C2 120.91(11) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 121.61(11) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C14 C5 C4 123.75(10) . . ?
C14 C5 C6 119.29(10) . . ?
C4 C5 C6 116.97(10) . . ?
C7 C6 C1 120.79(10) . . ?
C7 C6 C5 119.89(10) . . ?
C1 C6 C5 119.33(10) . . ?
C6 C7 C8 121.40(10) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 H7 119.3 . . ?
C7 C8 C9 121.63(11) . . ?
C7 C8 C13 119.36(10) . . ?
C9 C8 C13 119.01(10) . . ?
C10 C9 C8 121.11(11) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C9 C10 C11 120.28(11) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 120.58(11) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 121.37(11) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C14 C13 C12 122.27(10) . . ?
C14 C13 C8 120.10(10) . . ?
C12 C13 C8 117.62(10) . . ?
C13 C14 C5 119.94(10) . . ?
C13 C14 C15 118.82(9) . . ?
C5 C14 C15 121.16(10) . . ?
N1 C15 C14 115.13(9) . . ?
N1 C15 H15A 107.0(7) . . ?
C14 C15 H15A 109.0(7) . . ?
N1 C15 H15B 109.7(7) . . ?
C14 C15 H15B 110.8(7) . . ?
H15A C15 H15B 104.7(10) . . ?
C17 N1 C18 109.66(8) . . ?
C17 N1 C15 111.59(8) . . ?
C18 N1 C15 108.68(8) . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N1 C18 C19 111.37(8) . . ?
N1 C18 H18A 109.4 . . ?
C19 C18 H18A 109.4 . . ?
N1 C18 H18B 109.4 . . ?
C19 C18 H18B 109.4 . . ?
H18A C18 H18B 108.0 . . ?
C20 C19 C24 120.15(10) . . ?
C20 C19 C18 118.91(10) . . ?
C24 C19 C18 120.93(10) . . ?
C21 C20 C19 120.93(11) . . ?
C21 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C22 C21 C20 119.56(11) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C21 C22 C23 119.90(11) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C22 C23 C24 121.86(11) . . ?
C22 C23 H23 119.1 . . ?
C24 C23 H23 119.1 . . ?
C23 C24 C19 117.55(10) . . ?
C23 C24 B1 118.64(10) . . ?
C19 C24 B1 123.81(10) . . ?
O1 B1 O2 119.97(11) . . ?
O1 B1 C24 117.41(10) . . ?
O2 B1 C24 122.61(10) . . ?
B1 O1 H1O 115.2(10) . . ?
B1 O2 H2O 110.2(9) . . ?
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
C1 C2 1.3544(17) . ?
C1 C6 1.4345(15) . ?
C1 H1 0.9500 . ?
C2 C3 1.4169(17) . ?
C2 H2 0.9500 . ?
C3 C4 1.3616(16) . ?
C3 H3 0.9500 . ?
C4 C5 1.4343(15) . ?
C4 H4 0.9500 . ?
C5 C14 1.4147(14) . ?
C5 C6 1.4429(15) . ?
C6 C7 1.3923(16) . ?
C7 C8 1.3952(16) . ?
C7 H7 0.9500 . ?
C8 C9 1.4292(16) . ?
C8 C13 1.4362(15) . ?
C9 C10 1.3569(18) . ?
C9 H9 0.9500 . ?
C10 C11 1.4152(18) . ?
C10 H10 0.9500 . ?
C11 C12 1.3632(16) . ?
C11 H11 0.9500 . ?
C12 C13 1.4312(15) . ?
C12 H12 0.9500 . ?
C13 C14 1.4126(15) . ?
C14 C15 1.5086(15) . ?
C15 N1 1.4826(13) . ?
C15 H15A 0.989(13) . ?
C15 H15B 1.006(13) . ?
N1 C17 1.4705(13) . ?
N1 C18 1.4813(14) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.5108(15) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.3949(15) . ?
C19 C24 1.4124(15) . ?
C20 C21 1.3893(17) . ?
C20 H20 0.9500 . ?
C21 C22 1.3841(18) . ?
C21 H21 0.9500 . ?
C22 C23 1.3886(17) . ?
C22 H22 0.9500 . ?
C23 C24 1.4021(15) . ?
C23 H23 0.9500 . ?
C24 B1 1.5837(17) . ?
B1 O1 1.3560(15) . ?
B1 O2 1.3653(15) . ?
O1 H1O 0.887(16) . ?
O2 H2O 0.903(15) . ?
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 0.32(17) . . . . ?
C1 C2 C3 C4 0.48(18) . . . . ?
C2 C3 C4 C5 -0.35(18) . . . . ?
C3 C4 C5 C14 179.51(11) . . . . ?
C3 C4 C5 C6 -0.54(16) . . . . ?
C2 C1 C6 C7 179.01(10) . . . . ?
C2 C1 C6 C5 -1.22(16) . . . . ?
C14 C5 C6 C7 1.02(15) . . . . ?
C4 C5 C6 C7 -178.93(10) . . . . ?
C14 C5 C6 C1 -178.75(10) . . . . ?
C4 C5 C6 C1 1.30(14) . . . . ?
C1 C6 C7 C8 -179.81(10) . . . . ?
C5 C6 C7 C8 0.42(16) . . . . ?
C6 C7 C8 C9 178.16(10) . . . . ?
C6 C7 C8 C13 -1.63(16) . . . . ?
C7 C8 C9 C10 -179.64(11) . . . . ?
C13 C8 C9 C10 0.15(17) . . . . ?
C8 C9 C10 C11 -0.99(18) . . . . ?
C9 C10 C11 C12 0.37(18) . . . . ?
C10 C11 C12 C13 1.11(17) . . . . ?
C11 C12 C13 C14 177.73(10) . . . . ?
C11 C12 C13 C8 -1.90(16) . . . . ?
C7 C8 C13 C14 1.41(15) . . . . ?
C9 C8 C13 C14 -178.38(10) . . . . ?
C7 C8 C13 C12 -178.95(10) . . . . ?
C9 C8 C13 C12 1.26(15) . . . . ?
C12 C13 C14 C5 -179.61(10) . . . . ?
C8 C13 C14 C5 0.02(15) . . . . ?
C12 C13 C14 C15 3.54(15) . . . . ?
C8 C13 C14 C15 -176.84(9) . . . . ?
C4 C5 C14 C13 178.73(10) . . . . ?
C6 C5 C14 C13 -1.22(15) . . . . ?
C4 C5 C14 C15 -4.49(15) . . . . ?
C6 C5 C14 C15 175.56(9) . . . . ?
C13 C14 C15 N1 -71.75(12) . . . . ?
C5 C14 C15 N1 111.43(11) . . . . ?
C14 C15 N1 C17 -55.83(12) . . . . ?
C14 C15 N1 C18 -176.88(9) . . . . ?
C17 N1 C18 C19 174.29(9) . . . . ?
C15 N1 C18 C19 -63.49(11) . . . . ?
N1 C18 C19 C20 108.87(11) . . . . ?
N1 C18 C19 C24 -69.87(12) . . . . ?
C24 C19 C20 C21 1.99(16) . . . . ?
C18 C19 C20 C21 -176.76(10) . . . . ?
C19 C20 C21 C22 -0.34(17) . . . . ?
C20 C21 C22 C23 -1.62(18) . . . . ?
C21 C22 C23 C24 1.96(19) . . . . ?
C22 C23 C24 C19 -0.32(17) . . . . ?
C22 C23 C24 B1 179.53(11) . . . . ?
C20 C19 C24 C23 -1.63(16) . . . . ?
C18 C19 C24 C23 177.09(10) . . . . ?
C20 C19 C24 B1 178.52(10) . . . . ?
C18 C19 C24 B1 -2.76(16) . . . . ?
C23 C24 B1 O1 34.08(16) . . . . ?
C19 C24 B1 O1 -146.07(11) . . . . ?
C23 C24 B1 O2 -144.77(12) . . . . ?
C19 C24 B1 O2 35.08(18) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 8104193
2 PubChem 9928560
