#------------------------------------------------------------------------------
#$Date: 2020-05-05 15:27:40 +0200 (mar 05 de may de 2020) $
#$Revision: 251653 $
#$URL: svn://www.crystallography.net/cod/cif/7/70/37/7703780.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_7703780
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             2019-04-30T12:43:07-00:00
_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                 102.4210(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.68950(10)
_cell_length_b                   4.72070(10)
_cell_length_c                   18.1961(2)
_cell_measurement_reflns_used    17518
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.69
_cell_measurement_theta_min      3.041
_cell_volume                     1232.27(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.48a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.48a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.48a (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 1
_diffrn_measured_fraction_theta_max 0.989
_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      -0.0389347
_diffrn_orient_matrix_UB_12      -0.2703978
_diffrn_orient_matrix_UB_13      -0.0428695
_diffrn_orient_matrix_UB_21      0.0802218
_diffrn_orient_matrix_UB_22      0.0049025
_diffrn_orient_matrix_UB_23      -0.0423533
_diffrn_orient_matrix_UB_31      0.0598465
_diffrn_orient_matrix_UB_32      -0.1826202
_diffrn_orient_matrix_UB_33      0.062321
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_unetI/netI     0.0516
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            32221
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.543
_diffrn_reflns_theta_min         3.08
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.164
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.213
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.40.48a (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    1.617
_exptl_crystal_description       blade
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.471
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2579
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0348
_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)+(0.0601P)²+0.3520P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1033
_reflns_Friedel_coverage         0
_reflns_number_gt                2410
_reflns_number_total             2579
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0dt00745e2.cif
_cod_data_source_block           4a
_cod_depositor_comments
'Adding full bibliography for 7703777--7703788.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7703780
_shelx_estimated_absorpt_t_min   0.61
_shelx_estimated_absorpt_t_max   0.933
_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
F1 F 0.67007(4) 0.86067(15) 0.83958(4) 0.02681(18) Uani 1 1 d . . . . .
F2 F 0.93569(5) 1.37229(15) 0.94918(4) 0.03119(19) Uani 1 1 d . . . . .
F3 F 0.95615(4) 0.68890(15) 0.76956(4) 0.03067(19) Uani 1 1 d . . . . .
O1 O 0.81340(5) 0.40035(16) 0.69540(4) 0.02197(19) Uani 1 1 d . . . . .
O2 O 0.66996(5) 0.45349(16) 0.73685(4) 0.02087(19) Uani 1 1 d . . . . .
C1 C 0.80852(7) 0.7568(2) 0.79824(6) 0.0197(2) Uani 1 1 d . . . . .
C2 C 0.76145(7) 0.9120(2) 0.84402(6) 0.0205(2) Uani 1 1 d . . . . .
C3 C 0.80089(7) 1.1181(2) 0.89495(6) 0.0227(2) Uani 1 1 d . . . . .
H3 H 0.765469 1.217643 0.924564 0.027 Uiso 1 1 calc R U . . .
C4 C 0.89451(8) 1.1716(2) 0.90047(6) 0.0233(2) Uani 1 1 d . . . . .
C5 C 0.94781(7) 1.0321(2) 0.85852(6) 0.0241(2) Uani 1 1 d . . . . .
H5 H 1.012111 1.073299 0.863241 0.029 Uiso 1 1 calc R U . . .
C6 C 0.90298(7) 0.8284(2) 0.80902(6) 0.0222(2) Uani 1 1 d . . . . .
C7 C 0.77440(7) 0.1965(2) 0.64361(6) 0.0210(2) Uani 1 1 d . . . . .
C8 C 0.67998(7) 0.1213(2) 0.63852(6) 0.0197(2) Uani 1 1 d . . . . .
C9 C 0.62743(7) 0.2502(2) 0.68574(6) 0.0201(2) Uani 1 1 d . . . . .
C10 C 0.53654(7) 0.1786(2) 0.68229(6) 0.0227(2) Uani 1 1 d . . . . .
H10 H 0.50189 0.267278 0.714348 0.027 Uiso 1 1 calc R U . . .
C11 C 0.49502(7) -0.0307(2) 0.62997(6) 0.0246(2) Uani 1 1 d . . . . .
H11 H 0.431989 -0.083068 0.627499 0.029 Uiso 1 1 calc R U . . .
C12 C 0.54350(8) -0.1592(2) 0.58285(6) 0.0245(2) Uani 1 1 d . . . . .
H12 H 0.513605 -0.29777 0.548023 0.029 Uiso 1 1 calc R U . . .
C13 C 0.63796(7) -0.0877(2) 0.58552(6) 0.0215(2) Uani 1 1 d . . . . .
C14 C 0.69320(8) -0.2122(2) 0.53906(6) 0.0250(2) Uani 1 1 d . . . . .
H14 H 0.666607 -0.35022 0.502746 0.03 Uiso 1 1 calc R U . . .
C15 C 0.78476(8) -0.1349(2) 0.54619(6) 0.0257(2) Uani 1 1 d . . . . .
H15 H 0.820756 -0.221876 0.514873 0.031 Uiso 1 1 calc R U . . .
C16 C 0.82674(8) 0.0715(2) 0.59914(6) 0.0242(2) Uani 1 1 d . . . . .
H16 H 0.890292 0.122178 0.603651 0.029 Uiso 1 1 calc R U . . .
B1 B 0.76103(8) 0.5256(3) 0.74029(7) 0.0201(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'
F F 0.0727 0.0534 '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
8 0 4 0.045
-8 0 -4 0.0648
4 -2 7 0.1236
-6 0 11 0.0479
-5 0 -9 0.0394
5 0 9 0.0379
-3 3 -5 0.1778
8 -1 5 0.0488
-9 -1 2 0.1023
7 0 -10 0.0455
1 1 -11 0.0866
2 0 -12 0.0228
-2 0 12 0.0371
1 0 11 0.0359
-1 0 -11 0.0266
2 0 11 0.0353
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 C7 120.20(9) . . ?
B1 O2 C9 119.81(9) . . ?
C2 C1 C6 113.07(9) . . ?
C2 C1 B1 123.92(9) . . ?
C6 C1 B1 123.01(10) . . ?
F1 C2 C3 115.77(9) . . ?
F1 C2 C1 118.89(9) . . ?
C3 C2 C1 125.34(10) . . ?
C4 C3 C2 116.41(10) . . ?
C4 C3 H3 121.8 . . ?
C2 C3 H3 121.8 . . ?
F2 C4 C5 118.26(10) . . ?
F2 C4 C3 118.37(10) . . ?
C5 C4 C3 123.36(10) . . ?
C4 C5 C6 116.52(10) . . ?
C4 C5 H5 121.7 . . ?
C6 C5 H5 121.7 . . ?
F3 C6 C5 116.05(9) . . ?
F3 C6 C1 118.66(10) . . ?
C5 C6 C1 125.28(10) . . ?
C16 C7 O1 120.11(9) . . ?
C16 C7 C8 121.46(10) . . ?
O1 C7 C8 118.43(9) . . ?
C9 C8 C7 120.58(10) . . ?
C9 C8 C13 119.82(9) . . ?
C7 C8 C13 119.60(10) . . ?
C10 C9 O2 119.78(10) . . ?
C10 C9 C8 121.52(10) . . ?
O2 C9 C8 118.70(9) . . ?
C9 C10 C11 118.64(10) . . ?
C9 C10 H10 120.7 . . ?
C11 C10 H10 120.7 . . ?
C12 C11 C10 121.58(10) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C11 C12 C13 120.66(10) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C13 C14 124.15(10) . . ?
C12 C13 C8 117.79(10) . . ?
C14 C13 C8 118.06(10) . . ?
C15 C14 C13 120.51(10) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C16 121.48(10) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
C7 C16 C15 118.88(10) . . ?
C7 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
O2 B1 O1 122.27(10) . . ?
O2 B1 C1 119.43(10) . . ?
O1 B1 C1 118.30(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
F1 C2 1.3492(11) . ?
F2 C4 1.3486(12) . ?
F3 C6 1.3419(13) . ?
O1 B1 1.3707(14) . ?
O1 C7 1.3819(13) . ?
O2 B1 1.3688(14) . ?
O2 C9 1.3879(12) . ?
C1 C2 1.3987(15) . ?
C1 C6 1.4004(14) . ?
C1 B1 1.5729(16) . ?
C2 C3 1.3820(15) . ?
C3 C4 1.3805(15) . ?
C3 H3 0.95 . ?
C4 C5 1.3735(16) . ?
C5 C6 1.3833(15) . ?
C5 H5 0.95 . ?
C7 C16 1.3646(16) . ?
C7 C8 1.4154(14) . ?
C8 C9 1.4105(15) . ?
C8 C13 1.4240(15) . ?
C9 C10 1.3657(15) . ?
C10 C11 1.4157(15) . ?
C10 H10 0.95 . ?
C11 C12 1.3686(17) . ?
C11 H11 0.95 . ?
C12 C13 1.4189(15) . ?
C12 H12 0.95 . ?
C13 C14 1.4191(16) . ?
C14 C15 1.3726(16) . ?
C14 H14 0.95 . ?
C15 C16 1.4150(16) . ?
C15 H15 0.95 . ?
C16 H16 0.95 . ?
