#------------------------------------------------------------------------------
#$Date: 2020-05-05 16:27:40 +0300 (Tue, 05 May 2020) $
#$Revision: 251653 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/37/7703783.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_7703783
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            'C16 H8 B F3 O2'
_chemical_formula_weight         300.03
_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             2018-05-28T11:37:16-00:00
_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                90
_cell_angle_beta                 102.643(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.000(2)
_cell_length_b                   9.222(2)
_cell_length_c                   15.177(3)
_cell_measurement_reflns_used    1528
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.26
_cell_measurement_theta_min      2.32
_cell_volume                     1229.1(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '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  0.0464
_diffrn_reflns_av_unetI/netI     0.0518
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7797
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.444
_diffrn_reflns_theta_min         2.319
_exptl_absorpt_coefficient_mu    0.135
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5830
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_description       blade
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.425
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2270
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0419
_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)+(0.0423P)²+0.2792P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.096
_refine_ls_wR_factor_ref         0.1066
_reflns_Friedel_coverage         0
_reflns_number_gt                1588
_reflns_number_total             2270
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0dt00745e2.cif
_cod_data_source_block           3a
_cod_depositor_comments
'Adding full bibliography for 7703777--7703788.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7703783
_shelx_estimated_absorpt_t_min   0.945
_shelx_estimated_absorpt_t_max   0.996
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
F1 F 0.89775(15) 0.63385(14) 0.78837(8) 0.0263(4) Uani 1 1 d . . . . .
F2 F 1.05881(14) 0.78237(14) 0.68842(9) 0.0261(4) Uani 1 1 d . . . . .
F3 F 1.01378(14) 0.73461(13) 0.50906(9) 0.0226(3) Uani 1 1 d . . . . .
O1 O 0.53619(16) 0.29383(15) 0.56959(9) 0.0157(4) Uani 1 1 d . . . . .
O2 O 0.61517(16) 0.33486(15) 0.43024(10) 0.0164(4) Uani 1 1 d . . . . .
C1 C 0.4299(2) 0.1906(2) 0.52847(14) 0.0144(5) Uani 1 1 d . . . . .
C2 C 0.4188(2) 0.1609(2) 0.43591(14) 0.0150(5) Uani 1 1 d . . . . .
C3 C 0.5122(2) 0.2312(2) 0.38642(15) 0.0149(5) Uani 1 1 d . . . . .
C4 C 0.5062(3) 0.2007(2) 0.29802(15) 0.0178(5) Uani 1 1 d . . . . .
H4 H 0.571472 0.248804 0.266002 0.021 Uiso 1 1 calc R U . . .
C5 C 0.4007(2) 0.0957(2) 0.25499(15) 0.0188(5) Uani 1 1 d . . . . .
H5 H 0.395352 0.072743 0.193355 0.023 Uiso 1 1 calc R U . . .
C6 C 0.3056(2) 0.0262(2) 0.30069(15) 0.0182(5) Uani 1 1 d . . . . .
H6 H 0.23464 -0.042929 0.269947 0.022 Uiso 1 1 calc R U . . .
C7 C 0.3117(2) 0.0559(2) 0.39264(15) 0.0153(5) Uani 1 1 d . . . . .
C8 C 0.2189(2) -0.0123(2) 0.44450(15) 0.0182(5) Uani 1 1 d . . . . .
H8 H 0.145614 -0.081973 0.416881 0.022 Uiso 1 1 calc R U . . .
C9 C 0.2330(2) 0.0207(2) 0.53395(15) 0.0169(5) Uani 1 1 d . . . . .
H9 H 0.169708 -0.026947 0.567434 0.02 Uiso 1 1 calc R U . . .
C10 C 0.3394(2) 0.1236(2) 0.57703(15) 0.0158(5) Uani 1 1 d . . . . .
H10 H 0.348003 0.146032 0.639036 0.019 Uiso 1 1 calc R U . . .
C11 C 0.7421(2) 0.4785(2) 0.56696(15) 0.0153(5) Uani 1 1 d . . . . .
C12 C 0.7669(2) 0.5053(2) 0.65965(15) 0.0171(5) Uani 1 1 d . . . . .
H12 H 0.710865 0.453074 0.695506 0.02 Uiso 1 1 calc R U . . .
C13 C 0.8720(2) 0.6068(2) 0.69892(15) 0.0184(5) Uani 1 1 d . . . . .
C14 C 0.9552(2) 0.6839(2) 0.64872(15) 0.0181(5) Uani 1 1 d . . . . .
C15 C 0.9310(2) 0.6581(2) 0.55698(15) 0.0159(5) Uani 1 1 d . . . . .
C16 C 0.8265(2) 0.5575(2) 0.51591(15) 0.0168(5) Uani 1 1 d . . . . .
H16 H 0.811263 0.541255 0.452755 0.02 Uiso 1 1 calc R U . . .
B1 B 0.6257(3) 0.3622(3) 0.52001(17) 0.0157(6) 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 0 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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
B1 O1 C1 119.72(17) . . ?
B1 O2 C3 119.69(17) . . ?
C10 C1 O1 120.02(19) . . ?
C10 C1 C2 122.0(2) . . ?
O1 C1 C2 117.97(18) . . ?
C3 C2 C1 121.5(2) . . ?
C3 C2 C7 119.5(2) . . ?
C1 C2 C7 118.98(19) . . ?
C4 C3 O2 119.41(19) . . ?
C4 C3 C2 122.2(2) . . ?
O2 C3 C2 118.35(19) . . ?
C3 C4 C5 118.4(2) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
C6 C5 C4 121.1(2) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C7 121.1(2) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C6 C7 C8 124.4(2) . . ?
C6 C7 C2 117.7(2) . . ?
C8 C7 C2 118.0(2) . . ?
C9 C8 C7 121.0(2) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C8 C9 C10 121.2(2) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C1 C10 C9 118.9(2) . . ?
C1 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
C12 C11 C16 118.5(2) . . ?
C12 C11 B1 121.7(2) . . ?
C16 C11 B1 119.7(2) . . ?
C13 C12 C11 120.1(2) . . ?
C13 C12 H12 120 . . ?
C11 C12 H12 120 . . ?
F1 C13 C12 120.9(2) . . ?
F1 C13 C14 117.8(2) . . ?
C12 C13 C14 121.3(2) . . ?
F2 C14 C13 120.5(2) . . ?
F2 C14 C15 120.56(19) . . ?
C13 C14 C15 118.9(2) . . ?
F3 C15 C16 120.9(2) . . ?
F3 C15 C14 117.99(19) . . ?
C16 C15 C14 121.1(2) . . ?
C15 C16 C11 120.1(2) . . ?
C15 C16 H16 119.9 . . ?
C11 C16 H16 119.9 . . ?
O2 B1 O1 122.7(2) . . ?
O2 B1 C11 118.4(2) . . ?
O1 B1 C11 118.9(2) . . ?
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
F1 C13 1.350(2) . ?
F2 C14 1.345(2) . ?
F3 C15 1.349(2) . ?
O1 B1 1.371(3) . ?
O1 C1 1.396(2) . ?
O2 B1 1.368(3) . ?
O2 C3 1.394(2) . ?
C1 C10 1.361(3) . ?
C1 C2 1.413(3) . ?
C2 C3 1.403(3) . ?
C2 C7 1.422(3) . ?
C3 C4 1.360(3) . ?
C4 C5 1.413(3) . ?
C4 H4 0.95 . ?
C5 C6 1.372(3) . ?
C5 H5 0.95 . ?
C6 C7 1.412(3) . ?
C6 H6 0.95 . ?
C7 C8 1.415(3) . ?
C8 C9 1.370(3) . ?
C8 H8 0.95 . ?
C9 C10 1.404(3) . ?
C9 H9 0.95 . ?
C10 H10 0.95 . ?
C11 C12 1.397(3) . ?
C11 C16 1.402(3) . ?
C11 B1 1.558(3) . ?
C12 C13 1.371(3) . ?
C12 H12 0.95 . ?
C13 C14 1.378(3) . ?
C14 C15 1.382(3) . ?
C15 C16 1.370(3) . ?
C16 H16 0.95 . ?
