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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/1/56/61/1566142.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_1566142
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 O'
_chemical_formula_sum            'C14 H8 Cl2 O'
_chemical_formula_weight         263.10
_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                 90.624(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4165(6)
_cell_length_b                   10.6043(7)
_cell_length_c                   14.6106(8)
_cell_measurement_reflns_used    2252
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.3460
_cell_measurement_theta_min      3.6370
_cell_volume                     1149.01(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    Sir2004
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 5.1856
_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  0.0238
_diffrn_reflns_av_sigmaI/netI    0.0276
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5621
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         3.35
_exptl_absorpt_coefficient_mu    0.541
_exptl_absorpt_correction_T_max  0.9734
_exptl_absorpt_correction_T_min  0.7736
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2034
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0401
_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)+(0.0379P)²+0.3274P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0886
_refine_ls_wR_factor_ref         0.0953
_reflns_number_gt                1624
_reflns_number_total             2034
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            Tetrahedron-2020-76-131299.cif
_cod_data_source_block           6
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1566142
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
C1 C 0.3676(3) 0.12242(19) 0.15981(13) 0.0423(5) Uani 1 1 d . . .
C2 C 0.4143(3) 0.2476(2) 0.15938(16) 0.0521(6) Uani 1 1 d . . .
H2 H 0.4527 0.2870 0.2130 0.063 Uiso 1 1 calc R . .
C3 C 0.4037(3) 0.3143(2) 0.07876(17) 0.0563(6) Uani 1 1 d . . .
H3 H 0.4367 0.3989 0.0778 0.068 Uiso 1 1 calc R . .
C4 C 0.3449(3) 0.2570(2) -0.00002(16) 0.0501(6) Uani 1 1 d . . .
H4 H 0.3368 0.3031 -0.0541 0.060 Uiso 1 1 calc R . .
C5 C 0.2971(3) 0.12965(18) 0.00057(13) 0.0387(5) Uani 1 1 d . . .
C6 C 0.2299(3) 0.0710(2) -0.08512(14) 0.0453(5) Uani 1 1 d . . .
C7 C 0.1817(3) -0.0647(2) -0.08409(13) 0.0402(5) Uani 1 1 d . . .
C8 C 0.1191(3) -0.1200(2) -0.16517(14) 0.0526(6) Uani 1 1 d . . .
H8 H 0.1083 -0.0717 -0.2181 0.063 Uiso 1 1 calc R . .
C9 C 0.0737(3) -0.2450(3) -0.16691(17) 0.0620(7) Uani 1 1 d . . .
H9 H 0.0312 -0.2814 -0.2208 0.074 Uiso 1 1 calc R . .
C10 C 0.0911(3) -0.3169(2) -0.08864(17) 0.0590(6) Uani 1 1 d . . .
H10 H 0.0610 -0.4021 -0.0898 0.071 Uiso 1 1 calc R . .
C11 C 0.1531(3) -0.2624(2) -0.00861(14) 0.0469(5) Uani 1 1 d . . .
C12 C 0.1985(2) -0.13525(18) -0.00371(13) 0.0369(5) Uani 1 1 d . . .
C13 C 0.2608(3) -0.07778(18) 0.08501(12) 0.0378(5) Uani 1 1 d . . .
H13A H 0.1662 -0.0886 0.1297 0.045 Uiso 1 1 calc R . .
H13B H 0.3654 -0.1243 0.1069 0.045 Uiso 1 1 calc R . .
C14 C 0.3090(2) 0.05923(18) 0.08108(12) 0.0351(4) Uani 1 1 d . . .
O1 O 0.2137(3) 0.13326(17) -0.15524(11) 0.0758(6) Uani 1 1 d . . .
Cl1 Cl 0.37772(10) 0.04135(6) 0.26312(4) 0.0695(2) Uani 1 1 d . . .
Cl2 Cl 0.17589(11) -0.35565(6) 0.08863(5) 0.0750(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 0.0033 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
C2 C1 C14 122.5(2) . .
C2 C1 Cl1 118.30(16) . .
C14 C1 Cl1 119.21(15) . .
C1 C2 C3 119.3(2) . .
C1 C2 H2 120.4 . .
C3 C2 H2 120.4 . .
C4 C3 C2 120.5(2) . .
C4 C3 H3 119.8 . .
C2 C3 H3 119.8 . .
C3 C4 C5 120.2(2) . .
C3 C4 H4 119.9 . .
C5 C4 H4 119.9 . .
C14 C5 C4 120.60(19) . .
C14 C5 C6 120.41(18) . .
C4 C5 C6 118.98(19) . .
O1 C6 C5 120.7(2) . .
O1 C6 C7 120.70(19) . .
C5 C6 C7 118.58(17) . .
C8 C7 C12 120.9(2) . .
C8 C7 C6 118.48(19) . .
C12 C7 C6 120.60(17) . .
C9 C8 C7 120.1(2) . .
C9 C8 H8 119.9 . .
C7 C8 H8 119.9 . .
C8 C9 C10 120.0(2) . .
C8 C9 H9 120.0 . .
C10 C9 H9 120.0 . .
C11 C10 C9 119.9(2) . .
C11 C10 H10 120.1 . .
C9 C10 H10 120.1 . .
C10 C11 C12 121.9(2) . .
C10 C11 Cl2 118.87(18) . .
C12 C11 Cl2 119.22(16) . .
C11 C12 C7 117.15(18) . .
C11 C12 C13 120.67(18) . .
C7 C12 C13 122.18(18) . .
C14 C13 C12 115.61(16) . .
C14 C13 H13A 108.4 . .
C12 C13 H13A 108.4 . .
C14 C13 H13B 108.4 . .
C12 C13 H13B 108.4 . .
H13A C13 H13B 107.4 . .
C5 C14 C1 117.00(18) . .
C5 C14 C13 122.59(17) . .
C1 C14 C13 120.41(17) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.372(3) .
C1 C14 1.397(3) .
C1 Cl1 1.738(2) .
C2 C3 1.375(3) .
C2 H2 0.9300 .
C3 C4 1.368(3) .
C3 H3 0.9300 .
C4 C5 1.397(3) .
C4 H4 0.9300 .
C5 C14 1.395(3) .
C5 C6 1.479(3) .
C6 O1 1.224(2) .
C6 C7 1.483(3) .
C7 C8 1.397(3) .
C7 C12 1.397(3) .
C8 C9 1.367(3) .
C8 H8 0.9300 .
C9 C10 1.380(3) .
C9 H9 0.9300 .
C10 C11 1.379(3) .
C10 H10 0.9300 .
C11 C12 1.391(3) .
C11 Cl2 1.738(2) .
C12 C13 1.501(3) .
C13 C14 1.498(3) .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
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 C3 -0.1(3) . . . .
Cl1 C1 C2 C3 -178.64(17) . . . .
C1 C2 C3 C4 0.9(3) . . . .
C2 C3 C4 C5 -0.8(3) . . . .
C3 C4 C5 C14 -0.2(3) . . . .
C3 C4 C5 C6 178.6(2) . . . .
C14 C5 C6 O1 177.7(2) . . . .
C4 C5 C6 O1 -1.1(3) . . . .
C14 C5 C6 C7 -2.0(3) . . . .
C4 C5 C6 C7 179.22(19) . . . .
O1 C6 C7 C8 0.6(3) . . . .
C5 C6 C7 C8 -179.70(18) . . . .
O1 C6 C7 C12 -179.3(2) . . . .
C5 C6 C7 C12 0.4(3) . . . .
C12 C7 C8 C9 -0.2(3) . . . .
C6 C7 C8 C9 179.9(2) . . . .
C7 C8 C9 C10 -0.5(3) . . . .
C8 C9 C10 C11 0.4(4) . . . .
C9 C10 C11 C12 0.4(3) . . . .
C9 C10 C11 Cl2 -179.32(18) . . . .
C10 C11 C12 C7 -1.1(3) . . . .
Cl2 C11 C12 C7 178.63(15) . . . .
C10 C11 C12 C13 178.3(2) . . . .
Cl2 C11 C12 C13 -2.0(3) . . . .
C8 C7 C12 C11 1.0(3) . . . .
C6 C7 C12 C11 -179.10(18) . . . .
C8 C7 C12 C13 -178.39(18) . . . .
C6 C7 C12 C13 1.5(3) . . . .
C11 C12 C13 C14 178.89(18) . . . .
C7 C12 C13 C14 -1.8(3) . . . .
C4 C5 C14 C1 0.9(3) . . . .
C6 C5 C14 C1 -177.80(17) . . . .
C4 C5 C14 C13 -179.48(19) . . . .
C6 C5 C14 C13 1.8(3) . . . .
C2 C1 C14 C5 -0.8(3) . . . .
Cl1 C1 C14 C5 177.73(14) . . . .
C2 C1 C14 C13 179.6(2) . . . .
Cl1 C1 C14 C13 -1.9(3) . . . .
C12 C13 C14 C5 0.1(3) . . . .
C12 C13 C14 C1 179.64(17) . . . .
