#------------------------------------------------------------------------------
#$Date: 2020-05-05 16:27:40 +0300 (Tue, 05 May 2020) $
#$Revision: 251653 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/37/7703787.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_7703787
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 O5'
_chemical_formula_weight         353.92
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-06-24T13:03:55-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2019-10-30 deposited with the CCDC.	2020-03-16 downloaded from the CCDC.
;
_cell_angle_alpha                87.668(2)
_cell_angle_beta                 82.555(2)
_cell_angle_gamma                67.591(2)
_cell_formula_units_Z            2
_cell_length_a                   7.4723(2)
_cell_length_b                   8.48060(10)
_cell_length_c                   13.3696(3)
_cell_measurement_reflns_used    11566
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.529
_cell_measurement_theta_min      3.319
_cell_volume                     776.61(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.56a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.56a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.56a (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                 'CCD plate'
_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      0.1713976
_diffrn_orient_matrix_UB_12      0.0547392
_diffrn_orient_matrix_UB_13      -0.0372919
_diffrn_orient_matrix_UB_21      0.1384611
_diffrn_orient_matrix_UB_22      -0.1887262
_diffrn_orient_matrix_UB_23      -0.0120625
_diffrn_orient_matrix_UB_31      -0.0442131
_diffrn_orient_matrix_UB_32      0.0001694
_diffrn_orient_matrix_UB_33      -0.1094049
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            21542
_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         77.3
_diffrn_reflns_theta_min         3.334
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.878
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.564
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.40.56a (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    1.513
_exptl_crystal_description       irregular
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.288
_exptl_crystal_size_mid          0.137
_exptl_crystal_size_min          0.075
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.17
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.09
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3205
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.09
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0333
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0481P)²+0.1439P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0923
_refine_ls_wR_factor_ref         0.095
_reflns_Friedel_coverage         0
_reflns_number_gt                2905
_reflns_number_total             3205
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0dt00745e2.cif
_cod_data_source_block           14a
_cod_depositor_comments
'Adding full bibliography for 7703777--7703788.cif.'
_cod_database_code               7703787
_shelx_estimated_absorpt_t_min   0.786
_shelx_estimated_absorpt_t_max   0.937
_shelx_shelxl_version_number     2018/3
loop_
_symmetry_equiv_pos_as_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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.84459(10) 0.85711(9) 0.66041(5) 0.02662(18) Uani 1 1 d . . . . .
O2 O 0.80506(10) 0.68593(9) 0.53169(5) 0.02604(18) Uani 1 1 d . . . . .
O3 O 0.67855(10) 0.67929(9) 0.84080(5) 0.02678(18) Uani 1 1 d . . . . .
O4 O 0.93127(10) 0.39717(9) 0.82876(5) 0.02735(18) Uani 1 1 d . . . . .
O5 O 0.87899(11) 0.56972(9) 0.68801(6) 0.03084(19) Uani 1 1 d . . . . .
C1 C 0.79789(14) 0.99778(13) 0.59761(8) 0.0247(2) Uani 1 1 d . . . . .
C2 C 0.74930(13) 0.98121(12) 0.50103(8) 0.0234(2) Uani 1 1 d . . . . .
C3 C 0.75655(14) 0.82275(13) 0.46688(8) 0.0242(2) Uani 1 1 d . . . . .
C4 C 0.71747(15) 0.80276(13) 0.37256(8) 0.0273(2) Uani 1 1 d . . . . .
H4 H 0.728048 0.694419 0.349993 0.033 Uiso 1 1 calc R U . . .
C5 C 0.66113(15) 0.94545(14) 0.30907(8) 0.0301(2) Uani 1 1 d . . . . .
H5 H 0.631529 0.932956 0.243575 0.036 Uiso 1 1 calc R U . . .
C6 C 0.64813(15) 1.10232(14) 0.33999(8) 0.0299(2) Uani 1 1 d . . . . .
H6 H 0.607008 1.197182 0.296305 0.036 Uiso 1 1 calc R U . . .
C7 C 0.69539(14) 1.12409(13) 0.43628(8) 0.0268(2) Uani 1 1 d . . . . .
C8 C 0.69386(15) 1.28038(13) 0.47197(9) 0.0305(2) Uani 1 1 d . . . . .
H8 H 0.655878 1.378786 0.430799 0.037 Uiso 1 1 calc R U . . .
C9 C 0.74648(16) 1.29024(13) 0.56486(9) 0.0318(3) Uani 1 1 d . . . . .
H9 H 0.747174 1.395265 0.586572 0.038 Uiso 1 1 calc R U . . .
C10 C 0.80000(15) 1.14797(13) 0.62961(8) 0.0284(2) Uani 1 1 d . . . . .
H10 H 0.836634 1.156681 0.693969 0.034 Uiso 1 1 calc R U . . .
C11 C 0.63813(15) 0.66132(13) 0.94348(8) 0.0252(2) Uani 1 1 d . . . . .
C12 C 0.74937(14) 0.50824(12) 0.98944(8) 0.0245(2) Uani 1 1 d . . . . .
C13 C 0.89622(15) 0.37474(13) 0.93115(8) 0.0253(2) Uani 1 1 d . . . . .
C14 C 1.00495(15) 0.22584(13) 0.97433(9) 0.0301(2) Uani 1 1 d . . . . .
H14 H 1.100709 0.135769 0.934047 0.036 Uiso 1 1 calc R U . . .
C15 C 0.97260(16) 0.20828(14) 1.07946(9) 0.0334(3) Uani 1 1 d . . . . .
H15 H 1.048835 0.105638 1.110024 0.04 Uiso 1 1 calc R U . . .
C16 C 0.83346(16) 0.33602(15) 1.13890(9) 0.0321(2) Uani 1 1 d . . . . .
H16 H 0.816082 0.321498 1.209846 0.039 Uiso 1 1 calc R U . . .
C17 C 0.71542(15) 0.48956(14) 1.09516(8) 0.0282(2) Uani 1 1 d . . . . .
C18 C 0.56722(16) 0.62683(15) 1.15138(9) 0.0319(2) Uani 1 1 d . . . . .
H18 H 0.541297 0.617605 1.222381 0.038 Uiso 1 1 calc R U . . .
C19 C 0.46146(16) 0.77250(14) 1.10371(9) 0.0324(3) Uani 1 1 d . . . . .
H19 H 0.362657 0.862793 1.142508 0.039 Uiso 1 1 calc R U . . .
C20 C 0.49561(15) 0.79173(13) 0.99854(9) 0.0286(2) Uani 1 1 d . . . . .
H20 H 0.420904 0.893459 0.966631 0.034 Uiso 1 1 calc R U . . .
B1 B 0.84025(17) 0.70831(15) 0.62668(9) 0.0262(2) Uani 1 1 d . . . . .
B2 B 0.83003(17) 0.55110(15) 0.78751(9) 0.0267(2) 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 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
0 0 -1 0.0591
2 1 0 0.1185
4 2 7 0.0905
0 0 9 0.0633
1 -4 -2 0.0404
-1 -3 -8 0.0427
-1 4 3 0.032
-4 1 0 0.0763
0 1 8 0.0585
-4 -3 -6 0.0827
-5 -4 0 0.1064
-3 -5 -5 0.0704
-2 -5 1 0.0767
0 -2 8 0.0629
0 2 -8 0.0719
0 -5 -2 0.0363
-1 4 -3 0.0629
4 -1 2 0.0954
1 -1 -8 0.0457
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 118.83(9) . . ?
B1 O2 C3 119.26(8) . . ?
B2 O3 C11 119.06(8) . . ?
B2 O4 C13 119.11(8) . . ?
B2 O5 B1 133.03(9) . . ?
C10 C1 O1 120.02(10) . . ?
C10 C1 C2 121.43(10) . . ?
O1 C1 C2 118.55(9) . . ?
C1 C2 C3 120.91(9) . . ?
C1 C2 C7 119.85(9) . . ?
C3 C2 C7 119.23(10) . . ?
C4 C3 O2 119.79(9) . . ?
C4 C3 C2 121.73(10) . . ?
O2 C3 C2 118.48(9) . . ?
C3 C4 C5 118.86(10) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C6 C5 C4 121.28(10) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C7 120.66(10) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C6 C7 C2 118.18(9) . . ?
C6 C7 C8 123.99(10) . . ?
C2 C7 C8 117.82(10) . . ?
C9 C8 C7 120.59(10) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C10 121.65(10) . . ?
C8 C9 H9 119.2 . . ?
C10 C9 H9 119.2 . . ?
C1 C10 C9 118.60(10) . . ?
C1 C10 H10 120.7 . . ?
C9 C10 H10 120.7 . . ?
C20 C11 O3 119.79(9) . . ?
C20 C11 C12 121.47(10) . . ?
O3 C11 C12 118.73(9) . . ?
C13 C12 C11 120.63(10) . . ?
C13 C12 C17 119.67(9) . . ?
C11 C12 C17 119.69(9) . . ?
C14 C13 O4 119.72(10) . . ?
C14 C13 C12 121.39(10) . . ?
O4 C13 C12 118.88(9) . . ?
C13 C14 C15 118.85(10) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
C16 C15 C14 121.52(10) . . ?
C16 C15 H15 119.2 . . ?
C14 C15 H15 119.2 . . ?
C15 C16 C17 120.47(10) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C12 C17 C16 118.07(10) . . ?
C12 C17 C18 118.09(10) . . ?
C16 C17 C18 123.83(10) . . ?
C19 C18 C17 120.35(10) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C20 121.67(10) . . ?
C18 C19 H19 119.2 . . ?
C20 C19 H19 119.2 . . ?
C11 C20 C19 118.72(10) . . ?
C11 C20 H20 120.6 . . ?
C19 C20 H20 120.6 . . ?
O5 B1 O2 116.09(9) . . ?
O5 B1 O1 120.13(10) . . ?
O2 B1 O1 123.75(10) . . ?
O5 B2 O4 116.60(10) . . ?
O5 B2 O3 120.12(10) . . ?
O4 B2 O3 123.19(10) . . ?
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 1.3704(14) . ?
O1 C1 1.3881(12) . ?
O2 B1 1.3647(15) . ?
O2 C3 1.3810(12) . ?
O3 B2 1.3735(14) . ?
O3 C11 1.3819(13) . ?
O4 B2 1.3701(13) . ?
O4 C13 1.3793(13) . ?
O5 B2 1.3524(14) . ?
O5 B1 1.3643(14) . ?
C1 C10 1.3664(14) . ?
C1 C2 1.4122(15) . ?
C2 C3 1.4161(14) . ?
C2 C7 1.4187(14) . ?
C3 C4 1.3619(15) . ?
C4 C5 1.4081(15) . ?
C4 H4 0.95 . ?
C5 C6 1.3734(15) . ?
C5 H5 0.95 . ?
C6 C7 1.4152(16) . ?
C6 H6 0.95 . ?
C7 C8 1.4223(15) . ?
C8 C9 1.3654(17) . ?
C8 H8 0.95 . ?
C9 C10 1.4148(16) . ?
C9 H9 0.95 . ?
C10 H10 0.95 . ?
C11 C20 1.3654(15) . ?
C11 C12 1.4138(14) . ?
C12 C13 1.4129(15) . ?
C12 C17 1.4167(15) . ?
C13 C14 1.3667(14) . ?
C14 C15 1.4066(16) . ?
C14 H14 0.95 . ?
C15 C16 1.3723(17) . ?
C15 H15 0.95 . ?
C16 C17 1.4183(15) . ?
C16 H16 0.95 . ?
C17 C18 1.4210(16) . ?
C18 C19 1.3707(16) . ?
C18 H18 0.95 . ?
C19 C20 1.4103(16) . ?
C19 H19 0.95 . ?
C20 H20 0.95 . ?
