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#$Date: 2022-01-26 14:50:01 +0200 (Wed, 26 Jan 2022) $
#$Revision: 272250 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/61/1566143.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_1566143
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         'C14 H8 Cl2 O2'
_chemical_formula_sum            'C14 H8 Cl2 O2'
_chemical_formula_weight         279.10
_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_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 108.504(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.7477(2)
_cell_length_b                   7.7582(2)
_cell_length_c                   20.4902(5)
_cell_measurement_reflns_used    3238
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.9990
_cell_measurement_theta_min      6.1240
_cell_volume                     1167.96(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    Sir2004
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1856
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'_diffrn_standards_number'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_sigmaI/netI    0.0277
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            6032
_diffrn_reflns_theta_full        66.59
_diffrn_reflns_theta_max         66.59
_diffrn_reflns_theta_min         6.14
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.915
_exptl_absorpt_correction_T_max  0.5900
_exptl_absorpt_correction_T_min  0.1565
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.587
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plaquet
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     171
_refine_ls_number_reflns         2047
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.956
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0357
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1171
_refine_ls_wR_factor_ref         0.1237
_reflns_number_gt                1828
_reflns_number_total             2047
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            Tetrahedron-2020-76-131299.cif
_cod_data_source_block           7
_cod_original_sg_symbol_Hall     '-P 2ybc '
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1566143
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 1.17801(7) 0.46000(8) 0.79991(2) 0.0639(2) Uani 1 1 d . . .
Cl2 Cl 1.43240(7) 0.66222(8) 1.05260(2) 0.0647(2) Uani 1 1 d . . .
O1 O 1.21618(19) 0.78938(18) 0.89745(6) 0.0465(3) Uani 1 1 d . . .
O2 O 0.5974(2) 0.8187(2) 0.91239(9) 0.0677(5) Uani 1 1 d . . .
C1 C 0.9660(3) 0.5291(2) 0.80191(9) 0.0466(4) Uani 1 1 d . . .
C2 C 0.9506(2) 0.6175(2) 0.85908(8) 0.0399(4) Uani 1 1 d . . .
C3 C 1.1166(2) 0.6569(2) 0.91908(8) 0.0385(4) Uani 1 1 d . . .
C4 C 1.0755(2) 0.7168(2) 0.98301(8) 0.0381(4) Uani 1 1 d . . .
C5 C 1.2124(3) 0.7277(2) 1.04572(9) 0.0441(4) Uani 1 1 d . . .
C6 C 1.1814(3) 0.7888(3) 1.10455(9) 0.0541(5) Uani 1 1 d . . .
H6 H 1.2756 0.7923 1.1461 0.065 Uiso 1 1 calc R . .
C7 C 1.0105(3) 0.8442(3) 1.10092(10) 0.0560(5) Uani 1 1 d . . .
H7 H 0.9892 0.8871 1.1401 0.067 Uiso 1 1 calc R . .
C8 C 0.8709(3) 0.8365(2) 1.03984(11) 0.0514(5) Uani 1 1 d . . .
H8 H 0.7555 0.8751 1.0376 0.062 Uiso 1 1 calc R . .
C9 C 0.9014(2) 0.7711(2) 0.98085(9) 0.0416(4) Uani 1 1 d . . .
C10 C 0.7470(2) 0.7589(2) 0.91651(10) 0.0458(4) Uani 1 1 d . . .
C11 C 0.7753(2) 0.6679(2) 0.85681(9) 0.0439(4) Uani 1 1 d . . .
C12 C 0.6244(3) 0.6295(3) 0.80058(11) 0.0566(5) Uani 1 1 d . . .
H12 H 0.5092 0.6650 0.7999 0.068 Uiso 1 1 calc R . .
C13 C 0.6453(3) 0.5389(3) 0.74572(11) 0.0621(6) Uani 1 1 d . . .
H13 H 0.5440 0.5121 0.7083 0.075 Uiso 1 1 calc R . .
C14 C 0.8160(3) 0.4878(3) 0.74621(10) 0.0561(5) Uani 1 1 d . . .
H14 H 0.8302 0.4259 0.7094 0.067 Uiso 1 1 calc R . .
H1O H 1.327(4) 0.770(4) 0.9125(14) 0.074(8) Uiso 1 1 d . . .
H3 H 1.192(3) 0.547(3) 0.9314(10) 0.046(5) Uiso 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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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_
_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
C3 O1 H1O 110.3(19) . .
C14 C1 C2 122.21(18) . .
C14 C1 Cl1 117.48(15) . .
C2 C1 Cl1 120.28(15) . .
C1 C2 C11 116.76(17) . .
C1 C2 C3 120.55(15) . .
C11 C2 C3 122.69(15) . .
O1 C3 C2 107.30(13) . .
O1 C3 C4 109.15(13) . .
C2 C3 C4 114.18(14) . .
O1 C3 H3 110.5(11) . .
C2 C3 H3 108.0(11) . .
C4 C3 H3 107.8(11) . .
C5 C4 C9 117.20(15) . .
C5 C4 C3 120.77(15) . .
C9 C4 C3 121.96(16) . .
C4 C5 C6 122.35(17) . .
C4 C5 Cl2 119.93(13) . .
C6 C5 Cl2 117.72(15) . .
C7 C6 C5 119.41(19) . .
C7 C6 H6 120.3 . .
C5 C6 H6 120.3 . .
C8 C7 C6 120.28(17) . .
C8 C7 H7 119.9 . .
C6 C7 H7 119.9 . .
C7 C8 C9 120.24(18) . .
C7 C8 H8 119.9 . .
C9 C8 H8 119.9 . .
C8 C9 C4 120.49(18) . .
C8 C9 C10 118.92(17) . .
C4 C9 C10 120.58(15) . .
O2 C10 C9 121.21(18) . .
O2 C10 C11 120.37(18) . .
C9 C10 C11 118.41(15) . .
C12 C11 C2 121.34(18) . .
C12 C11 C10 118.63(17) . .
C2 C11 C10 119.99(16) . .
C13 C12 C11 120.0(2) . .
C13 C12 H12 120.0 . .
C11 C12 H12 120.0 . .
C14 C13 C12 120.12(19) . .
C14 C13 H13 119.9 . .
C12 C13 H13 119.9 . .
C13 C14 C1 119.52(19) . .
C13 C14 H14 120.2 . .
C1 C14 H14 120.2 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C1 1.740(2) .
Cl2 C5 1.7408(19) .
O1 C3 1.437(2) .
O1 H1O 0.83(3) .
O2 C10 1.227(2) .
C1 C14 1.384(3) .
C1 C2 1.395(2) .
C2 C11 1.400(3) .
C2 C3 1.502(2) .
C3 C4 1.516(2) .
C3 H3 1.02(2) .
C4 C5 1.385(2) .
C4 C9 1.400(3) .
C5 C6 1.385(3) .
C6 C7 1.372(3) .
C6 H6 0.9300 .
C7 C8 1.371(3) .
C7 H7 0.9300 .
C8 C9 1.399(3) .
C8 H8 0.9300 .
C9 C10 1.476(3) .
C10 C11 1.488(3) .
C11 C12 1.388(3) .
C12 C13 1.378(3) .
C12 H12 0.9300 .
C13 C14 1.377(3) .
C13 H13 0.9300 .
C14 H14 0.9300 .
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
C14 C1 C2 C11 -1.9(3) . . . .
Cl1 C1 C2 C11 -179.70(13) . . . .
C14 C1 C2 C3 178.83(16) . . . .
Cl1 C1 C2 C3 1.1(2) . . . .
C1 C2 C3 O1 71.85(19) . . . .
C11 C2 C3 O1 -107.33(17) . . . .
C1 C2 C3 C4 -167.06(15) . . . .
C11 C2 C3 C4 13.8(2) . . . .
O1 C3 C4 C5 -71.83(19) . . . .
C2 C3 C4 C5 168.11(15) . . . .
O1 C3 C4 C9 105.01(18) . . . .
C2 C3 C4 C9 -15.1(2) . . . .
C9 C4 C5 C6 0.2(3) . . . .
C3 C4 C5 C6 177.17(17) . . . .
C9 C4 C5 Cl2 179.85(13) . . . .
C3 C4 C5 Cl2 -3.2(2) . . . .
C4 C5 C6 C7 -1.4(3) . . . .
Cl2 C5 C6 C7 178.97(15) . . . .
C5 C6 C7 C8 1.0(3) . . . .
C6 C7 C8 C9 0.5(3) . . . .
C7 C8 C9 C4 -1.7(3) . . . .
C7 C8 C9 C10 177.87(17) . . . .
C5 C4 C9 C8 1.3(2) . . . .
C3 C4 C9 C8 -175.63(15) . . . .
C5 C4 C9 C10 -178.22(16) . . . .
C3 C4 C9 C10 4.8(2) . . . .
C8 C9 C10 O2 6.5(3) . . . .
C4 C9 C10 O2 -174.01(17) . . . .
C8 C9 C10 C11 -171.97(15) . . . .
C4 C9 C10 C11 7.6(2) . . . .
C1 C2 C11 C12 0.8(3) . . . .
C3 C2 C11 C12 179.98(17) . . . .
C1 C2 C11 C10 178.50(15) . . . .
C3 C2 C11 C10 -2.3(2) . . . .
O2 C10 C11 C12 -9.5(3) . . . .
C9 C10 C11 C12 168.91(17) . . . .
O2 C10 C11 C2 172.68(18) . . . .
C9 C10 C11 C2 -8.9(2) . . . .
C2 C11 C12 C13 0.5(3) . . . .
C10 C11 C12 C13 -177.24(17) . . . .
C11 C12 C13 C14 -0.7(3) . . . .
C12 C13 C14 C1 -0.4(3) . . . .
C2 C1 C14 C13 1.8(3) . . . .
Cl1 C1 C14 C13 179.62(16) . . . .
