#------------------------------------------------------------------------------
#$Date: 2020-05-05 15:27:40 +0200 (mar 05 de may de 2020) $
#$Revision: 251653 $
#$URL: svn://www.crystallography.net/cod/cif/7/70/37/7703777.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_7703777
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 H11 B O2'
_chemical_formula_weight         246.06
_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             2019-10-29T16:21:27-00:00
_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                 102.366(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.8170(2)
_cell_length_b                   4.72630(10)
_cell_length_c                   18.1904(3)
_cell_measurement_reflns_used    10088
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.955
_cell_measurement_theta_min      2.476
_cell_volume                     1160.33(4)
_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 0.999
_diffrn_measured_fraction_theta_max 0.979
_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      -0.0857722
_diffrn_orient_matrix_UB_12      -0.1877262
_diffrn_orient_matrix_UB_13      0.0132861
_diffrn_orient_matrix_UB_21      0.020528
_diffrn_orient_matrix_UB_22      0.0945992
_diffrn_orient_matrix_UB_23      0.0829505
_diffrn_orient_matrix_UB_31      -0.0724333
_diffrn_orient_matrix_UB_32      0.2491238
_diffrn_orient_matrix_UB_33      -0.0215219
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.05
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_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            19552
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.519
_diffrn_reflns_theta_min         3.274
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.722
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.537
_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    1.409
_exptl_crystal_description       needle
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.613
_exptl_crystal_size_mid          0.108
_exptl_crystal_size_min          0.061
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2402
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0418
_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)+(0.0528P)²+0.4848P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1113
_refine_ls_wR_factor_ref         0.1135
_reflns_Friedel_coverage         0
_reflns_number_gt                2218
_reflns_number_total             2402
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0dt00745e2.cif
_cod_data_source_block           1a
_cod_depositor_comments
'Adding full bibliography for 7703777--7703788.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7703777
_shelx_estimated_absorpt_t_min   0.666
_shelx_estimated_absorpt_t_max   0.957
_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 0.17994(6) 0.42199(18) 0.30652(5) 0.0212(2) Uani 1 1 d . . . . .
O2 O 0.33331(6) 0.47150(18) 0.26534(4) 0.0210(2) Uani 1 1 d . . . . .
C1 C 0.22097(9) 0.2165(3) 0.35800(6) 0.0198(3) Uani 1 1 d . . . . .
C2 C 0.32069(9) 0.1374(3) 0.36256(6) 0.0191(3) Uani 1 1 d . . . . .
C3 C 0.37720(9) 0.2644(3) 0.31528(6) 0.0199(3) Uani 1 1 d . . . . .
C4 C 0.47291(9) 0.1856(3) 0.31791(7) 0.0227(3) Uani 1 1 d . . . . .
H4 H 0.509948 0.271829 0.285591 0.027 Uiso 1 1 calc R U . . .
C5 C 0.51610(9) -0.0263(3) 0.36953(7) 0.0238(3) Uani 1 1 d . . . . .
H5 H 0.582648 -0.082197 0.371499 0.029 Uiso 1 1 calc R U . . .
C6 C 0.46407(9) -0.1526(3) 0.41669(7) 0.0233(3) Uani 1 1 d . . . . .
H6 H 0.494968 -0.293558 0.451061 0.028 Uiso 1 1 calc R U . . .
C7 C 0.36448(9) -0.0749(3) 0.41467(6) 0.0206(3) Uani 1 1 d . . . . .
C8 C 0.30535(9) -0.1981(3) 0.46125(7) 0.0231(3) Uani 1 1 d . . . . .
H8 H 0.333061 -0.337947 0.497141 0.028 Uiso 1 1 calc R U . . .
C9 C 0.20887(9) -0.1169(3) 0.45479(7) 0.0237(3) Uani 1 1 d . . . . .
H9 H 0.170357 -0.203492 0.486006 0.028 Uiso 1 1 calc R U . . .
C10 C 0.16510(9) 0.0929(3) 0.40276(7) 0.0223(3) Uani 1 1 d . . . . .
H10 H 0.097998 0.147051 0.398969 0.027 Uiso 1 1 calc R U . . .
C11 C 0.18847(8) 0.7776(3) 0.20379(6) 0.0196(3) Uani 1 1 d . . . . .
C12 C 0.24351(9) 0.9080(3) 0.15703(7) 0.0217(3) Uani 1 1 d . . . . .
H12 H 0.310966 0.856916 0.161187 0.026 Uiso 1 1 calc R U . . .
C13 C 0.20121(9) 1.1110(3) 0.10461(7) 0.0237(3) Uani 1 1 d . . . . .
H13 H 0.239615 1.197162 0.073254 0.028 Uiso 1 1 calc R U . . .
C14 C 0.10280(9) 1.1874(3) 0.09815(7) 0.0243(3) Uani 1 1 d . . . . .
H14 H 0.073691 1.325377 0.062172 0.029 Uiso 1 1 calc R U . . .
C15 C 0.04679(9) 1.0623(3) 0.14429(7) 0.0239(3) Uani 1 1 d . . . . .
H15 H -0.020453 1.115672 0.140146 0.029 Uiso 1 1 calc R U . . .
C16 C 0.08935(9) 0.8590(3) 0.19652(7) 0.0223(3) Uani 1 1 d . . . . .
H16 H 0.050602 0.773888 0.227786 0.027 Uiso 1 1 calc R U . . .
B1 B 0.23615(10) 0.5457(3) 0.26134(7) 0.0199(3) 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
-8 0 -2 0.0162
-6 2 -1 0.1888
0 -3 0 0.2969
-3 0 12 0.0525
3 0 -12 0.0505
-2 2 -9 0.1332
6 -2 -1 0.2426
5 -2 2 0.2365
9 0 -5 0.042
8 1 -6 0.0895
8 0 4 0.0386
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 120.03(10) . . ?
B1 O2 C3 120.07(10) . . ?
C10 C1 O1 120.08(11) . . ?
C10 C1 C2 121.33(11) . . ?
O1 C1 C2 118.59(10) . . ?
C1 C2 C3 120.73(11) . . ?
C1 C2 C7 119.72(11) . . ?
C3 C2 C7 119.55(11) . . ?
C4 C3 O2 120.06(11) . . ?
C4 C3 C2 121.36(11) . . ?
O2 C3 C2 118.57(10) . . ?
C3 C4 C5 118.96(11) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C6 C5 C4 121.42(11) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C7 120.54(11) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C6 C7 C8 123.86(11) . . ?
C6 C7 C2 118.16(11) . . ?
C8 C7 C2 117.98(11) . . ?
C9 C8 C7 120.51(11) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C10 121.57(11) . . ?
C8 C9 H9 119.2 . . ?
C10 C9 H9 119.2 . . ?
C1 C10 C9 118.89(11) . . ?
C1 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
C12 C11 C16 117.96(11) . . ?
C12 C11 B1 120.71(11) . . ?
C16 C11 B1 121.33(11) . . ?
C13 C12 C11 121.16(11) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C14 C13 C12 119.89(11) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C15 120.04(11) . . ?
C13 C14 H14 120 . . ?
C15 C14 H14 120 . . ?
C14 C15 C16 119.87(11) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C15 C16 C11 121.08(11) . . ?
C15 C16 H16 119.5 . . ?
C11 C16 H16 119.5 . . ?
O2 B1 O1 121.99(11) . . ?
O2 B1 C11 118.82(11) . . ?
O1 B1 C11 119.19(11) . . ?
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 1.3762(16) . ?
O1 C1 1.3836(14) . ?
O2 B1 1.3743(16) . ?
O2 C3 1.3839(14) . ?
C1 C10 1.3673(17) . ?
C1 C2 1.4127(16) . ?
C2 C3 1.4130(17) . ?
C2 C7 1.4235(16) . ?
C3 C4 1.3647(17) . ?
C4 C5 1.4147(17) . ?
C4 H4 0.95 . ?
C5 C6 1.3687(18) . ?
C5 H5 0.95 . ?
C6 C7 1.4170(17) . ?
C6 H6 0.95 . ?
C7 C8 1.4216(17) . ?
C8 C9 1.3679(18) . ?
C8 H8 0.95 . ?
C9 C10 1.4141(17) . ?
C9 H9 0.95 . ?
C10 H10 0.95 . ?
C11 C12 1.3996(17) . ?
C11 C16 1.4013(16) . ?
C11 B1 1.5606(18) . ?
C12 C13 1.3901(17) . ?
C12 H12 0.95 . ?
C13 C14 1.3873(18) . ?
C13 H13 0.95 . ?
C14 C15 1.3895(18) . ?
C14 H14 0.95 . ?
C15 C16 1.3902(17) . ?
C15 H15 0.95 . ?
C16 H16 0.95 . ?
