#------------------------------------------------------------------------------
#$Date: 2022-01-26 14:50:01 +0200 (Wed, 26 Jan 2022) $
#$Revision: 272250 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/61/1566146.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_1566146
loop_
_publ_author_name
'Forensi, Silvia'
'Stopin, Antoine'
'de Leo, Federica'
'Wouters, Johan'
'Bonifazi, Davide'
_publ_section_title
;
 1,8,10-Trisubstituted anthracenyl hydrocarbons: Towards versatile
 scaffolds for multiple-H-bonded recognition arrays
;
_journal_issue                   51
_journal_name_full               Tetrahedron
_journal_page_first              131299
_journal_paper_doi               10.1016/j.tet.2020.131299
_journal_volume                  76
_journal_year                    2020
_chemical_formula_moiety         'C11 H15 B O3'
_chemical_formula_sum            'C11 H15 B O3'
_chemical_formula_weight         206.04
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                93.205(4)
_cell_angle_beta                 94.213(4)
_cell_angle_gamma                109.868(5)
_cell_formula_units_Z            2
_cell_length_a                   6.9873(4)
_cell_length_b                   7.9428(4)
_cell_length_c                   11.0964(6)
_cell_measurement_reflns_used    2969
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.6658
_cell_measurement_theta_min      3.1613
_cell_volume                     575.46(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3712
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_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  0.0148
_diffrn_reflns_av_sigmaI/netI    0.0180
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4333
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         3.17
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9835
_exptl_absorpt_correction_T_min  0.9795
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             220
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2033
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0498
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0912P)²+0.0955P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1523
_refine_ls_wR_factor_ref         0.1586
_reflns_number_gt                1768
_reflns_number_total             2033
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            Tetrahedron-2020-76-131299.cif
_cod_data_source_block           10
_cod_original_cell_volume        575.46(5)
_cod_database_code               1566146
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.29806(19) 0.62578(17) 0.39586(13) 0.0665(4) Uani 1 1 d . . .
H1A H -0.4067 0.6338 0.4304 0.100 Uiso 1 1 d R . .
O2 O -0.39602(18) 0.34256(17) 0.46945(12) 0.0647(4) Uani 1 1 d . . .
H2A H -0.3807 0.2441 0.4591 0.097 Uiso 1 1 d R . .
O3 O -0.2270(2) 0.09670(17) 0.47116(13) 0.0701(4) Uani 1 1 d . . .
C1 C -0.0888(2) 0.4402(2) 0.33686(14) 0.0469(4) Uani 1 1 d . . .
C2 C -0.0150(3) 0.2951(2) 0.33827(15) 0.0514(4) Uani 1 1 d . . .
C3 C 0.1496(3) 0.2999(3) 0.27372(17) 0.0632(5) Uani 1 1 d . . .
H3 H 0.1979 0.2043 0.2752 0.076 Uiso 1 1 calc R . .
C4 C 0.2438(3) 0.4418(3) 0.20759(17) 0.0633(5) Uani 1 1 d . . .
H4 H 0.3535 0.4402 0.1655 0.076 Uiso 1 1 calc R . .
C5 C 0.1768(3) 0.5863(2) 0.20326(15) 0.0531(4) Uani 1 1 d . . .
C6 C 0.0118(2) 0.5804(2) 0.26922(15) 0.0509(4) Uani 1 1 d . . .
H6 H -0.0340 0.6774 0.2678 0.061 Uiso 1 1 calc R . .
C7 C -0.0897(3) 0.1358(3) 0.40609(18) 0.0641(5) Uani 1 1 d . . .
H7 H -0.0221 0.0537 0.3979 0.077 Uiso 1 1 calc R . .
C8 C 0.2819(3) 0.7501(3) 0.13571(17) 0.0645(5) Uani 1 1 d . . .
C9 C 0.4034(7) 0.7062(4) 0.0387(4) 0.163(2) Uani 1 1 d . . .
H9A H 0.3134 0.6138 -0.0192 0.244 Uiso 1 1 calc R . .
H9B H 0.5063 0.6651 0.0755 0.244 Uiso 1 1 calc R . .
H9C H 0.4675 0.8120 -0.0016 0.244 Uiso 1 1 calc R . .
C10 C 0.4187(4) 0.8966(3) 0.2289(3) 0.0996(8) Uani 1 1 d . . .
H10A H 0.3381 0.9222 0.2890 0.149 Uiso 1 1 calc R . .
H10B H 0.4828 1.0032 0.1894 0.149 Uiso 1 1 calc R . .
H10C H 0.5218 0.8570 0.2671 0.149 Uiso 1 1 calc R . .
C11 C 0.1251(5) 0.8204(4) 0.0727(3) 0.1179(11) Uani 1 1 d . . .
H11A H 0.0372 0.7298 0.0130 0.177 Uiso 1 1 calc R . .
H11B H 0.1952 0.9262 0.0340 0.177 Uiso 1 1 calc R . .
H11C H 0.0449 0.8495 0.1318 0.177 Uiso 1 1 calc R . .
B1 B -0.2708(3) 0.4667(3) 0.40517(17) 0.0505(5) 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 0.0000 0.0000 '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'
O O 0.0106 0.0060 '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
B1 O1 H1A 113.9 . .
B1 O2 H2A 111.5 . .
C6 C1 C2 116.38(14) . .
C6 C1 B1 115.23(14) . .
C2 C1 B1 128.38(15) . .
C3 C2 C1 119.28(15) . .
C3 C2 C7 113.98(15) . .
C1 C2 C7 126.70(15) . .
C4 C3 C2 122.14(16) . .
C4 C3 H3 118.9 . .
C2 C3 H3 118.9 . .
C3 C4 C5 120.66(16) . .
C3 C4 H4 119.7 . .
C5 C4 H4 119.7 . .
C4 C5 C6 116.67(16) . .
C4 C5 C8 122.52(16) . .
C6 C5 C8 120.74(16) . .
C1 C6 C5 124.88(15) . .
C1 C6 H6 117.6 . .
C5 C6 H6 117.6 . .
O3 C7 C2 128.87(16) . .
O3 C7 H7 115.6 . .
C2 C7 H7 115.6 . .
C9 C8 C10 111.1(3) . .
C9 C8 C5 111.73(18) . .
C10 C8 C5 107.54(16) . .
C9 C8 C11 107.2(3) . .
C10 C8 C11 108.1(2) . .
C5 C8 C11 111.11(16) . .
C8 C9 H9A 109.5 . .
C8 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C8 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
C8 C10 H10A 109.5 . .
C8 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C8 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
C8 C11 H11A 109.5 . .
C8 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C8 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
O1 B1 O2 119.33(15) . .
O1 B1 C1 115.87(15) . .
O2 B1 C1 124.80(15) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 B1 1.349(2) .
O1 H1A 0.8942 .
O2 B1 1.353(2) .
O2 H2A 0.8277 .
O3 C7 1.209(2) .
C1 C6 1.392(2) .
C1 C2 1.414(2) .
C1 B1 1.594(2) .
C2 C3 1.390(2) .
C2 C7 1.468(2) .
C3 C4 1.379(3) .
C3 H3 0.9300 .
C4 C5 1.381(3) .
C4 H4 0.9300 .
C5 C6 1.399(2) .
C5 C8 1.528(2) .
C6 H6 0.9300 .
C7 H7 0.9300 .
C8 C9 1.515(3) .
C8 C10 1.517(3) .
C8 C11 1.532(4) .
C9 H9A 0.9600 .
C9 H9B 0.9600 .
C9 H9C 0.9600 .
C10 H10A 0.9600 .
C10 H10B 0.9600 .
C10 H10C 0.9600 .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C6 C1 C2 C3 0.0(2) . . . .
B1 C1 C2 C3 -178.68(16) . . . .
C6 C1 C2 C7 177.50(16) . . . .
B1 C1 C2 C7 -1.2(3) . . . .
C1 C2 C3 C4 -0.2(3) . . . .
C7 C2 C3 C4 -178.06(17) . . . .
C2 C3 C4 C5 0.1(3) . . . .
C3 C4 C5 C6 0.3(3) . . . .
C3 C4 C5 C8 177.33(17) . . . .
C2 C1 C6 C5 0.5(3) . . . .
B1 C1 C6 C5 179.31(15) . . . .
C4 C5 C6 C1 -0.6(3) . . . .
C8 C5 C6 C1 -177.68(16) . . . .
C3 C2 C7 O3 178.7(2) . . . .
C1 C2 C7 O3 1.1(3) . . . .
C4 C5 C8 C9 22.4(3) . . . .
C6 C5 C8 C9 -160.8(3) . . . .
C4 C5 C8 C10 -99.8(2) . . . .
C6 C5 C8 C10 77.1(2) . . . .
C4 C5 C8 C11 142.1(2) . . . .
C6 C5 C8 C11 -41.1(3) . . . .
C6 C1 B1 O1 -4.0(2) . . . .
C2 C1 B1 O1 174.72(16) . . . .
C6 C1 B1 O2 175.75(16) . . . .
C2 C1 B1 O2 -5.6(3) . . . .
