#------------------------------------------------------------------------------
#$Date: 2020-05-05 16:27:40 +0300 (Tue, 05 May 2020) $
#$Revision: 251653 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/37/7703778.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_7703778
loop_
_publ_author_name
'Manankandayalage, Chamila P.'
'Unruh, Daniel K.'
'Krempner, Clemens'
_publ_section_title
;
 Boronic, diboronic and boric acid esters of 1,8-naphthalenediol -
 synthesis, structure and formation of boronium salts.
;
_journal_issue                   15
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              4834
_journal_page_last               4842
_journal_paper_doi               10.1039/d0dt00745e
_journal_volume                  49
_journal_year                    2020
_chemical_formula_sum            'C20 H12 B2 O4'
_chemical_formula_weight         337.92
_chemical_properties_physical    Air-sensitive
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-11-13T10:02:07-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2019-11-13 deposited with the CCDC.	2020-03-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.641(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.3335(2)
_cell_length_b                   5.12500(10)
_cell_length_c                   12.2086(3)
_cell_measurement_reflns_used    4368
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.976
_cell_measurement_theta_min      3.625
_cell_volume                     758.43(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0044137
_diffrn_orient_matrix_UB_12      0.0688769
_diffrn_orient_matrix_UB_13      0.1218865
_diffrn_orient_matrix_UB_21      -0.126957
_diffrn_orient_matrix_UB_22      -0.006059
_diffrn_orient_matrix_UB_23      -0.0275002
_diffrn_orient_matrix_UB_31      0.0016009
_diffrn_orient_matrix_UB_32      -0.2927434
_diffrn_orient_matrix_UB_33      0.02932
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.029
_diffrn_reflns_av_unetI/netI     0.0502
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10355
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         76.776
_diffrn_reflns_theta_min         3.646
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.819
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.744
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.40.63a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.48
_exptl_crystal_description       blade
_exptl_crystal_F_000             348
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.162
_exptl_crystal_size_mid          0.069
_exptl_crystal_size_min          0.009
_refine_diff_density_max         0.31
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.177
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         1559
_refine_ls_number_restraints     366
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0394
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0376P)²+0.2620P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.0981
_reflns_Friedel_coverage         0
_reflns_number_gt                1403
_reflns_number_total             1559
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0dt00745e2.cif
_cod_data_source_block           16a
_cod_depositor_comments
'Adding full bibliography for 7703777--7703788.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7703778
_shelx_estimated_absorpt_t_min   0.879
_shelx_estimated_absorpt_t_max   0.993
_shelx_shelxl_version_number     2018/3
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.35453(8) 0.0867(2) 0.41858(8) 0.0215(3) Uani 0.925(2) 1 d . U P A 1
O2 O 0.45718(8) 0.2956(2) 0.58122(8) 0.0216(3) Uani 0.925(2) 1 d . U P A 1
C1 C 0.26609(12) 0.2533(3) 0.41825(13) 0.0198(3) Uani 0.925(2) 1 d . . P A 1
C2 C 0.27444(13) 0.4468(3) 0.50212(12) 0.0200(3) Uani 0.925(2) 1 d . . P A 1
C3 C 0.37116(13) 0.4677(3) 0.58462(13) 0.0207(3) Uani 0.925(2) 1 d . . P A 1
C4 C 0.38097(15) 0.6512(4) 0.66689(14) 0.0241(4) Uani 0.925(2) 1 d . . P A 1
H4 H 0.4466 0.663743 0.721334 0.029 Uiso 0.925(2) 1 calc R U P A 1
C5 C 0.29164(15) 0.8220(4) 0.66949(16) 0.0272(4) Uani 0.925(2) 1 d . . P A 1
H5 H 0.297586 0.949583 0.726729 0.033 Uiso 0.925(2) 1 calc R U P A 1
C6 C 0.19670(15) 0.8078(4) 0.59140(14) 0.0256(4) Uani 0.925(2) 1 d . . P A 1
H6 H 0.137832 0.925057 0.595195 0.031 Uiso 0.925(2) 1 calc R U P A 1
C7 C 0.18543(13) 0.6195(3) 0.50476(13) 0.0223(4) Uani 0.925(2) 1 d . . P A 1
C8 C 0.08970(14) 0.5918(4) 0.42021(14) 0.0253(4) Uani 0.925(2) 1 d . . P A 1
H8 H 0.02884 0.706066 0.41903 0.03 Uiso 0.925(2) 1 calc R U P A 1
C9 C 0.08476(14) 0.4010(4) 0.34033(15) 0.0254(4) Uani 0.925(2) 1 d . . P A 1
H9 H 0.019921 0.384917 0.285045 0.03 Uiso 0.925(2) 1 calc R U P A 1
C10 C 0.17329(14) 0.2286(4) 0.33829(14) 0.0228(4) Uani 0.925(2) 1 d . . P A 1
H10 H 0.168577 0.097893 0.282447 0.027 Uiso 0.925(2) 1 calc R U P A 1
B1 B 0.44720(13) 0.1063(3) 0.50007(13) 0.0214(3) Uani 0.925(2) 1 d . U P A 1
O3 O 0.1447(12) 0.912(3) 0.5834(11) 0.028(3) Uani 0.075(2) 1 d . U P A 2
O4 O 0.0407(11) 0.712(3) 0.4192(11) 0.030(3) Uani 0.075(2) 1 d . U P A 2
B2 B 0.0516(18) 0.889(4) 0.5013(19) 0.029(4) Uani 0.075(2) 1 d . U P A 2
C11 C 0.2291(11) 0.748(2) 0.5818(11) 0.019(3) Uani 0.075(2) 1 d G U P A 2
C12 C 0.3246(12) 0.769(3) 0.6621(10) 0.016(4) Uani 0.075(2) 1 d G U P A 2
H12 H 0.330054 0.89909 0.718126 0.019 Uiso 0.075(2) 1 calc R U P A 2
C13 C 0.4121(10) 0.599(3) 0.6604(10) 0.024(3) Uani 0.075(2) 1 d G U P A 2
H13 H 0.477327 0.612879 0.71526 0.028 Uiso 0.075(2) 1 calc R U P A 2
C14 C 0.4041(9) 0.408(3) 0.5784(10) 0.018(3) Uani 0.075(2) 1 d G U P A 2
H14 H 0.463894 0.291538 0.577247 0.022 Uiso 0.075(2) 1 calc R U P A 2
C15 C 0.3086(8) 0.387(2) 0.4981(8) 0.021(3) Uani 0.075(2) 1 d G U P A 2
C16 C 0.2212(8) 0.557(2) 0.4998(8) 0.015(3) Uani 0.075(2) 1 d G U P A 2
C17 C 0.1257(9) 0.536(3) 0.4196(11) 0.022(3) Uani 0.075(2) 1 d G U P A 2
C18 C 0.1177(11) 0.345(3) 0.3376(11) 0.022(4) Uani 0.075(2) 1 d G U P A 2
H18 H 0.05247 0.330885 0.282706 0.027 Uiso 0.075(2) 1 calc R U P A 2
C19 C 0.2052(12) 0.175(3) 0.3359(11) 0.025(3) Uani 0.075(2) 1 d G U P A 2
H19 H 0.199739 0.044668 0.279835 0.03 Uiso 0.075(2) 1 calc R U P A 2
C20 C 0.3007(11) 0.196(2) 0.4161(11) 0.019(3) Uani 0.075(2) 1 d G U P A 2
H20 H 0.360447 0.079786 0.414979 0.023 Uiso 0.075(2) 1 calc R U P A 2
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.009 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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.0071
-1 0 0 0.0017
0 -2 1 0.0374
0 2 -1 0.0337
0 -2 -1 0.0226
-2 0 8 0.0657
0 3 0 0.0386
1 1 -8 0.0887
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
B1 O1 C1 120.43(12) . . ?
B1 O2 C3 120.19(12) . . ?
C10 C1 O1 120.04(14) . . ?
C10 C1 C2 121.41(14) . . ?
O1 C1 C2 118.55(13) . . ?
C7 C2 C1 120.09(13) . . ?
C7 C2 C3 119.45(14) . . ?
C1 C2 C3 120.45(14) . . ?
C4 C3 O2 119.74(14) . . ?
C4 C3 C2 121.61(14) . . ?
O2 C3 C2 118.65(13) . . ?
C3 C4 C5 118.69(15) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
C6 C5 C4 121.49(15) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C7 120.55(16) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C2 C7 C6 118.20(14) . . ?
C2 C7 C8 117.65(15) . . ?
C6 C7 C8 124.15(15) . . ?
C9 C8 C7 120.47(16) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 121.73(15) . . ?
C8 C9 H9 119.1 . . ?
C10 C9 H9 119.1 . . ?
C1 C10 C9 118.64(15) . . ?
C1 C10 H10 120.7 . . ?
C9 C10 H10 120.7 . . ?
O1 B1 O2 121.69(13) . . ?
O1 B1 B1 119.20(16) . 3_656 ?
O2 B1 B1 119.11(16) . 3_656 ?
C11 O3 B2 118.6(14) . . ?
B2 O4 C17 117.9(14) . . ?
O4 B2 O3 123.7(18) . . ?
O4 B2 B2 118(2) . 3_576 ?
O3 B2 B2 118(2) . 3_576 ?
O3 C11 C12 120.0(9) . . ?
O3 C11 C16 120.0(9) . . ?
C12 C11 C16 120 . . ?
C11 C12 C13 120 . . ?
C11 C12 H12 120 . . ?
C13 C12 H12 120 . . ?
C14 C13 C12 120 . . ?
C14 C13 H13 120 . . ?
C12 C13 H13 120 . . ?
C15 C14 C13 120 . . ?
C15 C14 H14 120 . . ?
C13 C14 H14 120 . . ?
C14 C15 C16 120 . . ?
C14 C15 C20 120 . . ?
C16 C15 C20 120 . . ?
C15 C16 C17 120 . . ?
C15 C16 C11 120 . . ?
C17 C16 C11 120 . . ?
O4 C17 C18 120.3(9) . . ?
O4 C17 C16 119.7(9) . . ?
C18 C17 C16 120 . . ?
C17 C18 C19 120 . . ?
C17 C18 H18 120 . . ?
C19 C18 H18 120 . . ?
C20 C19 C18 120 . . ?
C20 C19 H19 120 . . ?
C18 C19 H19 120 . . ?
C19 C20 C15 120 . . ?
C19 C20 H20 120 . . ?
C15 C20 H20 120 . . ?
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
O1 B1 1.3734(18) . ?
O1 C1 1.3847(18) . ?
O2 B1 1.3756(19) . ?
O2 C3 1.3862(18) . ?
C1 C10 1.366(2) . ?
C1 C2 1.415(2) . ?
C2 C7 1.415(2) . ?
C2 C3 1.416(2) . ?
C3 C4 1.365(2) . ?
C4 C5 1.412(2) . ?
C4 H4 0.95 . ?
C5 C6 1.369(2) . ?
C5 H5 0.95 . ?
C6 C7 1.420(2) . ?
C6 H6 0.95 . ?
C7 C8 1.425(2) . ?
C8 C9 1.375(2) . ?
C8 H8 0.95 . ?
C9 C10 1.408(2) . ?
C9 H9 0.95 . ?
C10 H10 0.95 . ?
B1 B1 1.699(3) 3_656 ?
O3 C11 1.343(18) . ?
O3 B2 1.38(3) . ?
O4 B2 1.34(3) . ?
O4 C17 1.383(18) . ?
B2 B2 1.70(4) 3_576 ?
C11 C12 1.39 . ?
C11 C16 1.39 . ?
C12 C13 1.39 . ?
C12 H12 0.95 . ?
C13 C14 1.39 . ?
C13 H13 0.95 . ?
C14 C15 1.39 . ?
C14 H14 0.95 . ?
C15 C16 1.39 . ?
C15 C20 1.39 . ?
C16 C17 1.39 . ?
C17 C18 1.39 . ?
C18 C19 1.39 . ?
C18 H18 0.95 . ?
C19 C20 1.39 . ?
C19 H19 0.95 . ?
C20 H20 0.95 . ?
