#------------------------------------------------------------------------------
#$Date: 2020-05-05 16:27:40 +0300 (Tue, 05 May 2020) $
#$Revision: 251653 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/37/7703781.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_7703781
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 H6 B F5 O2'
_chemical_formula_weight         336.02
_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             2019-10-29T13:49:35-00:00
_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                 103.8492(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.30604(7)
_cell_length_b                   9.01092(6)
_cell_length_c                   15.64505(12)
_cell_measurement_reflns_used    15496
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      77.344
_cell_measurement_theta_min      4.863
_cell_volume                     1273.792(17)
_computing_cell_refinement       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.59a (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 1
_diffrn_measured_fraction_theta_max 0.986
_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      -0.0435439
_diffrn_orient_matrix_UB_12      0.0181155
_diffrn_orient_matrix_UB_13      -0.1008424
_diffrn_orient_matrix_UB_21      -0.116494
_diffrn_orient_matrix_UB_22      0.1168871
_diffrn_orient_matrix_UB_23      0.0086969
_diffrn_orient_matrix_UB_31      0.1165964
_diffrn_orient_matrix_UB_32      0.123472
_diffrn_orient_matrix_UB_33      0.0065736
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            23436
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.286
_diffrn_reflns_theta_min         4.894
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.439
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.586
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.40.59a (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    1.752
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.262
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.113
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2676
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0329
_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)+(0.0560P)²+0.4823P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0941
_refine_ls_wR_factor_ref         0.0955
_reflns_Friedel_coverage         0
_reflns_number_gt                2542
_reflns_number_total             2676
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0dt00745e2.cif
_cod_data_source_block           2a
_cod_depositor_comments
'Adding full bibliography for 7703777--7703788.cif.'
_cod_original_cell_volume        1273.792(16)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7703781
_shelx_estimated_absorpt_t_min   0.704
_shelx_estimated_absorpt_t_max   0.854
_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 0.80961(7) 0.53625(7) 0.43678(4) 0.01703(17) Uani 1 1 d . . . . .
F2 F 1.01329(7) 0.72993(8) 0.51429(5) 0.02002(18) Uani 1 1 d . . . . .
F3 F 1.05900(8) 0.78735(8) 0.68943(5) 0.02388(18) Uani 1 1 d . . . . .
F4 F 0.89733(8) 0.64240(8) 0.78679(4) 0.02259(18) Uani 1 1 d . . . . .
F5 F 0.69106(7) 0.44763(8) 0.71137(4) 0.01871(17) Uani 1 1 d . . . . .
O1 O 0.53287(8) 0.29634(9) 0.57266(5) 0.01434(18) Uani 1 1 d . . . . .
O2 O 0.60327(9) 0.33702(9) 0.43655(5) 0.01497(18) Uani 1 1 d . . . . .
C1 C 0.42779(12) 0.19209(12) 0.53269(7) 0.0131(2) Uani 1 1 d . . . . .
C2 C 0.41254(11) 0.16010(12) 0.44266(7) 0.0134(2) Uani 1 1 d . . . . .
C3 C 0.50114(12) 0.23303(12) 0.39384(7) 0.0137(2) Uani 1 1 d . . . . .
C4 C 0.48932(12) 0.20328(13) 0.30697(7) 0.0166(2) Uani 1 1 d . . . . .
H4 H 0.549477 0.253962 0.275185 0.02 Uiso 1 1 calc R U . . .
C5 C 0.38563(13) 0.09537(13) 0.26511(7) 0.0182(2) Uani 1 1 d . . . . .
H5 H 0.377382 0.072813 0.204813 0.022 Uiso 1 1 calc R U . . .
C6 C 0.29665(13) 0.02259(13) 0.31006(7) 0.0176(2) Uani 1 1 d . . . . .
H6 H 0.227496 -0.048974 0.280387 0.021 Uiso 1 1 calc R U . . .
C7 C 0.30694(12) 0.05318(12) 0.40030(7) 0.0148(2) Uani 1 1 d . . . . .
C8 C 0.21872(12) -0.01692(13) 0.45121(8) 0.0167(2) Uani 1 1 d . . . . .
H8 H 0.147041 -0.088618 0.424623 0.02 Uiso 1 1 calc R U . . .
C9 C 0.23630(12) 0.01822(13) 0.53868(8) 0.0168(2) Uani 1 1 d . . . . .
H9 H 0.176066 -0.02969 0.571524 0.02 Uiso 1 1 calc R U . . .
C10 C 0.34190(12) 0.12398(12) 0.58083(7) 0.0153(2) Uani 1 1 d . . . . .
H10 H 0.352979 0.147238 0.641286 0.018 Uiso 1 1 calc R U . . .
C11 C 0.73954(12) 0.47986(12) 0.57013(7) 0.0136(2) Uani 1 1 d . . . . .
C12 C 0.82612(12) 0.55790(12) 0.52345(7) 0.0142(2) Uani 1 1 d . . . . .
C13 C 0.93263(12) 0.66020(12) 0.56223(8) 0.0158(2) Uani 1 1 d . . . . .
C14 C 0.95633(12) 0.68876(13) 0.65113(8) 0.0170(2) Uani 1 1 d . . . . .
C15 C 0.87407(13) 0.61500(13) 0.70042(7) 0.0169(2) Uani 1 1 d . . . . .
C16 C 0.76780(12) 0.51354(12) 0.65972(7) 0.0148(2) Uani 1 1 d . . . . .
B1 B 0.61911(13) 0.36334(13) 0.52427(8) 0.0133(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
4 4 -4 0.1053
1 3 -9 0.1137
-2 0 -9 0.0848
-4 -3 -3 0.0937
0 -2 9 0.1079
-6 -1 4 0.0464
-4 4 4 0.1255
5 3 -3 0.0876
6 0 -4 0.0833
2 -5 -4 0.1164
5 1 2 0.0609
4 -4 4 0.1047
-2 -6 2 0.1283
-6 -1 -1 0.057
-5 2 -2 0.0781
0 6 -3 0.1099
6 1 1 0.0556
1 -3 8 0.1033
3 4 4 0.119
1 3 8 0.1126
-2 0 10 0.0836
2 0 -10 0.112
0 5 5 0.1284
-5 3 -2 0.0771
6 0 1 0.0555
-1 5 -5 0.1087
-5 0 -3 0.0599
4 0 -9 0.107
1 0 9 0.0889
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 119.42(9) . . ?
B1 O2 C3 119.89(9) . . ?
C10 C1 O1 119.72(10) . . ?
C10 C1 C2 121.70(10) . . ?
O1 C1 C2 118.57(10) . . ?
C1 C2 C3 120.82(10) . . ?
C1 C2 C7 119.78(10) . . ?
C3 C2 C7 119.40(10) . . ?
C4 C3 O2 119.71(10) . . ?
C4 C3 C2 121.94(10) . . ?
O2 C3 C2 118.36(10) . . ?
C3 C4 C5 118.66(10) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
C6 C5 C4 121.24(10) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C7 120.73(10) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C6 C7 C8 124.11(10) . . ?
C6 C7 C2 118.02(10) . . ?
C8 C7 C2 117.87(10) . . ?
C9 C8 C7 120.53(10) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C10 121.54(10) . . ?
C8 C9 H9 119.2 . . ?
C10 C9 H9 119.2 . . ?
C1 C10 C9 118.57(10) . . ?
C1 C10 H10 120.7 . . ?
C9 C10 H10 120.7 . . ?
C16 C11 C12 114.90(10) . . ?
C16 C11 B1 122.95(10) . . ?
C12 C11 B1 122.15(10) . . ?
F1 C12 C13 115.92(10) . . ?
F1 C12 C11 120.88(10) . . ?
C13 C12 C11 123.20(10) . . ?
F2 C13 C14 120.13(10) . . ?
F2 C13 C12 120.42(10) . . ?
C14 C13 C12 119.45(10) . . ?
F3 C14 C13 120.04(10) . . ?
F3 C14 C15 120.14(10) . . ?
C13 C14 C15 119.82(11) . . ?
F4 C15 C14 119.84(10) . . ?
F4 C15 C16 120.72(10) . . ?
C14 C15 C16 119.44(10) . . ?
F5 C16 C15 116.15(10) . . ?
F5 C16 C11 120.67(10) . . ?
C15 C16 C11 123.18(10) . . ?
O2 B1 O1 122.88(10) . . ?
O2 B1 C11 117.82(10) . . ?
O1 B1 C11 119.27(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
F1 C12 1.3418(12) . ?
F2 C13 1.3381(13) . ?
F3 C14 1.3368(13) . ?
F4 C15 1.3392(13) . ?
F5 C16 1.3385(13) . ?
O1 B1 1.3684(15) . ?
O1 C1 1.3917(13) . ?
O2 B1 1.3655(14) . ?
O2 C3 1.3870(13) . ?
C1 C10 1.3678(15) . ?
C1 C2 1.4112(15) . ?
C2 C3 1.4130(15) . ?
C2 C7 1.4218(15) . ?
C3 C4 1.3637(16) . ?
C4 C5 1.4152(16) . ?
C4 H4 0.95 . ?
C5 C6 1.3744(17) . ?
C5 H5 0.95 . ?
C6 C7 1.4191(15) . ?
C6 H6 0.95 . ?
C7 C8 1.4214(16) . ?
C8 C9 1.3757(16) . ?
C8 H8 0.95 . ?
C9 C10 1.4137(16) . ?
C9 H9 0.95 . ?
C10 H10 0.95 . ?
C11 C16 1.3962(15) . ?
C11 C12 1.3996(15) . ?
C11 B1 1.5775(16) . ?
C12 C13 1.3829(16) . ?
C13 C14 1.3792(16) . ?
C14 C15 1.3803(17) . ?
C15 C16 1.3849(16) . ?
