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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/1/56/61/1566139.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_1566139
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         'C22 H16 Cl2 O4'
_chemical_formula_sum            'C22 H16 Cl2 O4'
_chemical_formula_weight         415.25
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 102.694(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.3773(8)
_cell_length_b                   20.523(3)
_cell_length_c                   12.5623(19)
_cell_measurement_reflns_used    1532
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.8140
_cell_measurement_theta_min      3.4680
_cell_volume                     1855.5(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 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0765
_diffrn_reflns_av_sigmaI/netI    0.0909
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10343
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         3.41
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.377
_exptl_absorpt_correction_T_max  0.9814
_exptl_absorpt_correction_T_min  0.8794
_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            colorless
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plaquet
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         3260
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.1134
_refine_ls_R_factor_gt           0.0597
_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)+(0.0226P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0864
_refine_ls_wR_factor_ref         0.1023
_reflns_number_gt                2028
_reflns_number_total             3260
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            Tetrahedron-2020-76-131299.cif
_cod_data_source_block           3
_cod_original_cell_volume        1855.5(4)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1566139
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 0.3835(4) 0.07771(15) 0.0050(3) 0.0338(8) Uani 1 1 d . . .
C2 C 0.4878(5) 0.10412(16) -0.0630(3) 0.0449(9) Uani 1 1 d . . .
H2 H 0.4365 0.1095 -0.1370 0.054 Uiso 1 1 calc R . .
C3 C 0.6693(5) 0.12251(17) -0.0199(3) 0.0509(10) Uani 1 1 d . . .
H3 H 0.7404 0.1405 -0.0651 0.061 Uiso 1 1 calc R . .
C4 C 0.7449(4) 0.11432(16) 0.0888(3) 0.0422(9) Uani 1 1 d . . .
H4 H 0.8667 0.1274 0.1169 0.051 Uiso 1 1 calc R . .
C5 C 0.6430(4) 0.08684(14) 0.1578(3) 0.0314(8) Uani 1 1 d . . .
C6 C 0.7264(4) 0.08036(16) 0.2786(3) 0.0320(8) Uani 1 1 d . . .
C7 C 0.6466(4) 0.02181(15) 0.3279(3) 0.0317(8) Uani 1 1 d . . .
C8 C 0.7517(4) -0.00732(18) 0.4201(3) 0.0463(10) Uani 1 1 d . . .
H8 H 0.8706 0.0081 0.4498 0.056 Uiso 1 1 calc R . .
C9 C 0.6816(5) -0.05917(18) 0.4684(3) 0.0518(10) Uani 1 1 d . . .
H9 H 0.7534 -0.0785 0.5305 0.062 Uiso 1 1 calc R . .
C10 C 0.5054(5) -0.08229(17) 0.4250(3) 0.0443(9) Uani 1 1 d . . .
H10 H 0.4594 -0.1181 0.4559 0.053 Uiso 1 1 calc R . .
C11 C 0.3985(4) -0.05179(16) 0.3353(3) 0.0362(8) Uani 1 1 d . . .
C12 C 0.4668(4) 0.00066(15) 0.2850(3) 0.0299(8) Uani 1 1 d . . .
C13 C 0.3537(4) 0.03631(15) 0.1899(3) 0.0306(8) Uani 1 1 d . . .
C14 C 0.4592(4) 0.06726(14) 0.1154(2) 0.0278(7) Uani 1 1 d . . .
C15 C 0.6896(4) 0.14192(15) 0.3401(3) 0.0315(8) Uani 1 1 d . . .
C16 C 0.8271(4) 0.16571(16) 0.4247(3) 0.0362(8) Uani 1 1 d . . .
H16 H 0.9420 0.1451 0.4425 0.043 Uiso 1 1 calc R . .
C17 C 0.7939(4) 0.21999(16) 0.4829(3) 0.0399(9) Uani 1 1 d . . .
C18 C 0.6222(5) 0.25025(16) 0.4576(3) 0.0441(9) Uani 1 1 d . . .
H18 H 0.6001 0.2871 0.4960 0.053 Uiso 1 1 calc R . .
C19 C 0.4843(4) 0.22566(16) 0.3755(3) 0.0398(9) Uani 1 1 d . . .
C20 C 0.5158(4) 0.17193(15) 0.3152(3) 0.0342(8) Uani 1 1 d . . .
H20 H 0.4224 0.1561 0.2590 0.041 Uiso 1 1 calc R . .
C21 C 1.0976(4) 0.21702(19) 0.5995(3) 0.0609(12) Uani 1 1 d . . .
H21A H 1.0825 0.1724 0.6188 0.091 Uiso 1 1 calc R . .
H21B H 1.1699 0.2397 0.6612 0.091 Uiso 1 1 calc R . .
H21C H 1.1600 0.2188 0.5401 0.091 Uiso 1 1 calc R . .
C22 C 0.1699(4) 0.23585(19) 0.2732(3) 0.0612(12) Uani 1 1 d . . .
H22A H 0.2061 0.2388 0.2045 0.092 Uiso 1 1 calc R . .
H22B H 0.0622 0.2625 0.2713 0.092 Uiso 1 1 calc R . .
H22C H 0.1413 0.1914 0.2867 0.092 Uiso 1 1 calc R . .
O1 O 0.1853(3) 0.04126(11) 0.17532(19) 0.0463(7) Uani 1 1 d . . .
O2 O 0.9238(3) 0.07485(13) 0.2986(2) 0.0453(7) Uani 1 1 d . . .
O3 O 0.9190(3) 0.24713(12) 0.5672(2) 0.0566(7) Uani 1 1 d . . .
O4 O 0.3186(3) 0.25801(12) 0.3584(2) 0.0585(7) Uani 1 1 d . . .
Cl1 Cl 0.15793(11) 0.05549(5) -0.05647(8) 0.0521(3) Uani 1 1 d . . .
Cl2 Cl 0.17949(12) -0.08426(5) 0.28633(9) 0.0623(3) Uani 1 1 d . . .
H2O H 0.944(5) 0.0507(18) 0.258(3) 0.059(15) 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 0.0033 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 121.4(3) . .
C2 C1 Cl1 116.0(3) . .
C14 C1 Cl1 122.6(2) . .
C1 C2 C3 119.3(3) . .
C1 C2 H2 120.4 . .
C3 C2 H2 120.4 . .
C4 C3 C2 120.3(3) . .
C4 C3 H3 119.8 . .
C2 C3 H3 119.8 . .
C3 C4 C5 121.1(3) . .
C3 C4 H4 119.5 . .
C5 C4 H4 119.5 . .
C4 C5 C14 119.4(3) . .
C4 C5 C6 120.4(3) . .
C14 C5 C6 120.1(3) . .
O2 C6 C5 111.0(2) . .
O2 C6 C7 109.6(3) . .
C5 C6 C7 111.6(2) . .
O2 C6 C15 105.2(2) . .
C5 C6 C15 110.8(3) . .
C7 C6 C15 108.4(2) . .
C8 C7 C12 120.2(3) . .
C8 C7 C6 119.0(3) . .
C12 C7 C6 120.6(3) . .
C7 C8 C9 120.5(3) . .
C7 C8 H8 119.8 . .
C9 C8 H8 119.8 . .
C10 C9 C8 120.2(3) . .
C10 C9 H9 119.9 . .
C8 C9 H9 119.9 . .
C11 C10 C9 119.3(3) . .
C11 C10 H10 120.4 . .
C9 C10 H10 120.4 . .
C10 C11 C12 121.5(3) . .
C10 C11 Cl2 116.0(3) . .
C12 C11 Cl2 122.4(3) . .
C7 C12 C11 118.3(3) . .
C7 C12 C13 118.5(3) . .
C11 C12 C13 123.2(3) . .
O1 C13 C14 121.8(3) . .
O1 C13 C12 122.3(3) . .
C14 C13 C12 115.9(2) . .
C1 C14 C5 118.5(3) . .
C1 C14 C13 122.8(3) . .
C5 C14 C13 118.7(3) . .
C16 C15 C20 119.9(3) . .
C16 C15 C6 119.7(3) . .
C20 C15 C6 120.4(3) . .
C17 C16 C15 120.3(3) . .
C17 C16 H16 119.9 . .
C15 C16 H16 119.9 . .
O3 C17 C16 124.9(3) . .
O3 C17 C18 115.1(3) . .
C16 C17 C18 120.0(3) . .
C19 C18 C17 119.8(3) . .
C19 C18 H18 120.1 . .
C17 C18 H18 120.1 . .
O4 C19 C18 115.4(3) . .
O4 C19 C20 123.5(3) . .
C18 C19 C20 121.1(3) . .
C19 C20 C15 119.0(3) . .
C19 C20 H20 120.5 . .
C15 C20 H20 120.5 . .
O3 C21 H21A 109.5 . .
O3 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
O3 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
O4 C22 H22A 109.5 . .
O4 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
O4 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
C6 O2 H2O 106(3) . .
C17 O3 C21 117.9(3) . .
C19 O4 C22 118.5(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.380(4) .
C1 C14 1.392(4) .
C1 Cl1 1.735(3) .
C2 C3 1.382(4) .
C2 H2 0.9300 .
C3 C4 1.367(5) .
C3 H3 0.9300 .
C4 C5 1.385(4) .
C4 H4 0.9300 .
C5 C14 1.402(4) .
C5 C6 1.513(4) .
C6 O2 1.426(3) .
C6 C7 1.528(4) .
C6 C15 1.536(4) .
C7 C8 1.380(4) .
C7 C12 1.387(4) .
C8 C9 1.381(5) .
C8 H8 0.9300 .
C9 C10 1.379(4) .
C9 H9 0.9300 .
C10 C11 1.375(5) .
C10 H10 0.9300 .
C11 C12 1.397(4) .
C11 Cl2 1.731(3) .
C12 C13 1.490(4) .
C13 O1 1.220(3) .
C13 C14 1.486(4) .
C15 C16 1.387(4) .
C15 C20 1.395(4) .
C16 C17 1.383(4) .
C16 H16 0.9300 .
C17 O3 1.362(4) .
C17 C18 1.383(4) .
C18 C19 1.375(4) .
C18 H18 0.9300 .
C19 O4 1.366(4) .
C19 C20 1.386(4) .
C20 H20 0.9300 .
C21 O3 1.431(4) .
C21 H21A 0.9600 .
C21 H21B 0.9600 .
C21 H21C 0.9600 .
C22 O4 1.428(4) .
C22 H22A 0.9600 .
C22 H22B 0.9600 .
C22 H22C 0.9600 .
O2 H2O 0.75(3) .
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 -2.1(5) . . . .
Cl1 C1 C2 C3 -179.5(3) . . . .
C1 C2 C3 C4 0.3(5) . . . .
C2 C3 C4 C5 0.8(5) . . . .
C3 C4 C5 C14 -0.2(5) . . . .
C3 C4 C5 C6 -177.8(3) . . . .
C4 C5 C6 O2 -27.9(4) . . . .
C14 C5 C6 O2 154.5(3) . . . .
C4 C5 C6 C7 -150.5(3) . . . .
C14 C5 C6 C7 31.9(4) . . . .
C4 C5 C6 C15 88.6(3) . . . .
C14 C5 C6 C15 -89.0(3) . . . .
O2 C6 C7 C8 30.6(4) . . . .
C5 C6 C7 C8 154.0(3) . . . .
C15 C6 C7 C8 -83.8(3) . . . .
O2 C6 C7 C12 -153.4(3) . . . .
C5 C6 C7 C12 -30.0(4) . . . .
C15 C6 C7 C12 92.3(3) . . . .
C12 C7 C8 C9 2.2(5) . . . .
C6 C7 C8 C9 178.2(3) . . . .
C7 C8 C9 C10 -0.1(5) . . . .
C8 C9 C10 C11 -2.1(5) . . . .
C9 C10 C11 C12 2.3(5) . . . .
C9 C10 C11 Cl2 179.9(3) . . . .
C8 C7 C12 C11 -2.0(5) . . . .
C6 C7 C12 C11 -178.0(3) . . . .
C8 C7 C12 C13 175.9(3) . . . .
C6 C7 C12 C13 0.0(4) . . . .
C10 C11 C12 C7 -0.2(5) . . . .
Cl2 C11 C12 C7 -177.7(2) . . . .
C10 C11 C12 C13 -178.1(3) . . . .
Cl2 C11 C12 C13 4.5(4) . . . .
C7 C12 C13 O1 -148.4(3) . . . .
C11 C12 C13 O1 29.4(5) . . . .
C7 C12 C13 C14 29.9(4) . . . .
C11 C12 C13 C14 -152.3(3) . . . .
C2 C1 C14 C5 2.7(5) . . . .
Cl1 C1 C14 C5 179.9(2) . . . .
C2 C1 C14 C13 -177.3(3) . . . .
Cl1 C1 C14 C13 -0.1(4) . . . .
C4 C5 C14 C1 -1.6(4) . . . .
C6 C5 C14 C1 176.0(3) . . . .
C4 C5 C14 C13 178.4(3) . . . .
C6 C5 C14 C13 -4.0(4) . . . .
O1 C13 C14 C1 -29.6(5) . . . .
C12 C13 C14 C1 152.1(3) . . . .
O1 C13 C14 C5 150.4(3) . . . .
C12 C13 C14 C5 -27.9(4) . . . .
O2 C6 C15 C16 -20.8(4) . . . .
C5 C6 C15 C16 -140.9(3) . . . .
C7 C6 C15 C16 96.4(3) . . . .
O2 C6 C15 C20 162.6(3) . . . .
C5 C6 C15 C20 42.5(4) . . . .
C7 C6 C15 C20 -80.2(4) . . . .
C20 C15 C16 C17 -1.5(5) . . . .
C6 C15 C16 C17 -178.1(3) . . . .
C15 C16 C17 O3 179.9(3) . . . .
C15 C16 C17 C18 0.9(5) . . . .
O3 C17 C18 C19 -178.3(3) . . . .
C16 C17 C18 C19 0.8(5) . . . .
C17 C18 C19 O4 178.6(3) . . . .
C17 C18 C19 C20 -1.8(5) . . . .
O4 C19 C20 C15 -179.3(3) . . . .
C18 C19 C20 C15 1.2(5) . . . .
C16 C15 C20 C19 0.5(5) . . . .
C6 C15 C20 C19 177.1(3) . . . .
C16 C17 O3 C21 -0.8(5) . . . .
C18 C17 O3 C21 178.3(3) . . . .
C18 C19 O4 C22 179.0(3) . . . .
C20 C19 O4 C22 -0.6(5) . . . .
