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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/1/56/61/1566141.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_1566141
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         'C15 H7 Cl2 F3 O3 S'
_chemical_formula_sum            'C15 H7 Cl2 F3 O3 S'
_chemical_formula_weight         395.17
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 102.298(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.1909(7)
_cell_length_b                   20.3736(17)
_cell_length_c                   17.2816(12)
_cell_measurement_reflns_used    2762
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.9240
_cell_measurement_theta_min      3.7680
_cell_volume                     3161.8(4)
_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    Sir2011
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 5.1856
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0269
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7122
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         3.76
_exptl_absorpt_coefficient_mu    0.586
_exptl_absorpt_correction_T_max  0.9224
_exptl_absorpt_correction_T_min  0.7621
_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            'clear light yellow'
_exptl_crystal_density_diffrn    1.660
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.952
_refine_diff_density_min         -1.045
_refine_diff_density_rms         0.118
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.590
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         2795
_refine_ls_number_restraints     20
_refine_ls_restrained_S_all      1.584
_refine_ls_R_factor_all          0.1441
_refine_ls_R_factor_gt           0.1193
_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)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3755
_refine_ls_wR_factor_ref         0.4091
_reflns_number_gt                1884
_reflns_number_total             2795
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            Tetrahedron-2020-76-131299.cif
_cod_data_source_block           5
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1566141
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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 0.0223(7) -0.0494(4) 0.1330(3) 0.086(2) Uani 1 1 d . . .
C2 C -0.1029(9) -0.0465(5) 0.0733(4) 0.097(2) Uani 1 1 d . . .
H2 H -0.1480 -0.0845 0.0499 0.116 Uiso 1 1 calc R . .
C3 C -0.1589(8) 0.0139(6) 0.0494(4) 0.101(3) Uani 1 1 d . . .
H3 H -0.2430 0.0164 0.0086 0.121 Uiso 1 1 calc R . .
C4 C -0.0974(6) 0.0703(4) 0.0826(3) 0.084(2) Uani 1 1 d . . .
H4 H -0.1408 0.1103 0.0650 0.101 Uiso 1 1 calc R . .
C5 C 0.0354(6) 0.0687(3) 0.1452(3) 0.0666(15) Uani 1 1 d . . .
C6 C 0.1062(6) 0.1221(3) 0.1825(3) 0.0686(16) Uani 1 1 d . A .
C7 C 0.2300(6) 0.1204(3) 0.2454(3) 0.0649(14) Uani 1 1 d . . .
C8 C 0.2993(8) 0.1778(3) 0.2855(4) 0.0853(19) Uani 1 1 d . . .
H8 H 0.2617 0.2192 0.2693 0.102 Uiso 1 1 calc R . .
C9 C 0.4150(9) 0.1727(4) 0.3448(5) 0.104(2) Uani 1 1 d . . .
H9 H 0.4556 0.2103 0.3715 0.124 Uiso 1 1 calc R . .
C10 C 0.4804(7) 0.1091(4) 0.3692(4) 0.095(2) Uani 1 1 d . . .
H10 H 0.5660 0.1058 0.4090 0.113 Uiso 1 1 calc R . .
C11 C 0.4143(6) 0.0549(4) 0.3330(3) 0.0766(18) Uani 1 1 d . . .
C12 C 0.2870(6) 0.0577(3) 0.2695(3) 0.0649(14) Uani 1 1 d . . .
C13 C 0.2182(6) 0.0016(3) 0.2329(3) 0.0686(15) Uani 1 1 d . . .
H13 H 0.2558 -0.0394 0.2504 0.082 Uiso 1 1 calc R . .
C14 C 0.0956(6) 0.0055(3) 0.1714(3) 0.0635(15) Uani 1 1 d . . .
Cl1 Cl 0.0943(3) -0.12778(11) 0.16051(15) 0.1254(10) Uani 1 1 d . . .
Cl2 Cl 0.48905(17) -0.02118(11) 0.36638(11) 0.1003(9) Uani 1 1 d . . .
O1 O 0.0440(5) 0.1858(2) 0.1598(2) 0.0814(13) Uani 1 1 d D . .
S1 S 0.1131(8) 0.2277(4) 0.0975(3) 0.122(3) Uani 0.45 1 d PD A 1
O2 O 0.2619(8) 0.2160(7) 0.0945(6) 0.112(3) Uani 0.45 1 d PD A 1
O3 O 0.0365(11) 0.2174(7) 0.0193(3) 0.199(8) Uani 0.45 1 d PD A 1
C15 C 0.0301(14) 0.3089(7) 0.1148(7) 0.30(2) Uani 0.45 1 d PD A 1
F1 F 0.110(3) 0.3426(16) 0.1742(10) 0.36(3) Uani 0.45 1 d PD A 1
F2 F -0.1043(17) 0.2986(10) 0.1279(15) 0.34(3) Uani 0.45 1 d PD A 1
F3 F 0.020(2) 0.3422(12) 0.0483(9) 0.166(9) Uani 0.45 1 d PD A 1
S1' S 0.0597(6) 0.2175(4) 0.0782(3) 0.0950(18) Uani 0.55 1 d PD A 2
O2' O 0.1791(9) 0.1898(6) 0.0513(5) 0.112(3) Uani 0.55 1 d PD A 2
O3' O -0.0590(9) 0.2133(7) 0.0125(5) 0.199(8) Uani 0.55 1 d PD A 2
C15' C 0.1007(12) 0.2947(5) 0.1137(6) 0.30(2) Uani 0.55 1 d PD A 2
F1' F 0.2359(14) 0.2909(6) 0.1586(7) 0.234(11) Uani 0.55 1 d PD A 2
F2' F 0.006(2) 0.3140(6) 0.1570(11) 0.34(2) Uani 0.55 1 d PD A 2
F3' F 0.1001(17) 0.3373(8) 0.0560(7) 0.145(6) Uani 0.55 1 d PD A 2
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'
F F 0.0171 0.0103 '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'
S S 0.1246 0.1234 '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 124.4(8) . .
C2 C1 Cl1 116.7(6) . .
C14 C1 Cl1 118.9(5) . .
C3 C2 C1 117.9(7) . .
C3 C2 H2 121.1 . .
C1 C2 H2 121.1 . .
C4 C3 C2 122.8(6) . .
C4 C3 H3 118.6 . .
C2 C3 H3 118.6 . .
C3 C4 C5 120.5(7) . .
C3 C4 H4 119.8 . .
C5 C4 H4 119.8 . .
C6 C5 C14 117.1(5) . .
C6 C5 C4 125.4(6) . .
C14 C5 C4 117.4(6) . .
C5 C6 C7 125.3(6) . .
C5 C6 O1 118.1(5) . .
C7 C6 O1 116.4(5) . .
C6 C7 C12 116.2(5) . .
C6 C7 C8 124.0(5) . .
C12 C7 C8 119.8(5) . .
C9 C8 C7 120.8(7) . .
C9 C8 H8 119.6 . .
C7 C8 H8 119.6 . .
C8 C9 C10 120.9(6) . .
C8 C9 H9 119.5 . .
C10 C9 H9 119.5 . .
C11 C10 C9 118.6(5) . .
C11 C10 H10 120.7 . .
C9 C10 H10 120.7 . .
C10 C11 C12 122.7(6) . .
C10 C11 Cl2 117.9(5) . .
C12 C11 Cl2 119.4(5) . .
C13 C12 C7 120.5(5) . .
C13 C12 C11 122.4(6) . .
C7 C12 C11 117.1(5) . .
C14 C13 C12 121.4(6) . .
C14 C13 H13 119.3 . .
C12 C13 H13 119.3 . .
C13 C14 C1 123.6(6) . .
C13 C14 C5 119.4(6) . .
C1 C14 C5 117.0(5) . .
C6 O1 S1' 120.3(4) . .
C6 O1 S1 118.1(4) . .
S1' O1 S1 20.6(3) . .
O2 S1 O3 103.53(10) . .
O2 S1 O1 117.6(7) . .
O3 S1 O1 112.2(5) . .
O2 S1 C15 126.2(9) . .
O3 S1 C15 98.5(6) . .
O1 S1 C15 97.5(6) . .
F1 C15 F2 109.55(12) . .
F1 C15 F3 109.54(12) . .
F2 C15 F3 109.52(12) . .
F1 C15 S1 114.0(14) . .
F2 C15 S1 108.3(11) . .
F3 C15 S1 105.8(12) . .
O2' S1' O3' 103.63(10) . .
O2' S1' O1 111.0(6) . .
O3' S1' O1 119.6(8) . .
O2' S1' C15' 111.3(8) . .
O3' S1' C15' 115.0(8) . .
O1 S1' C15' 96.4(5) . .
F2' C15' F1' 109.49(12) . .
F2' C15' F3' 109.49(12) . .
F1' C15' F3' 109.50(12) . .
F2' C15' S1' 111.0(7) . .
F1' C15' S1' 105.5(6) . .
F3' C15' S1' 111.8(8) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.374(10) .
C1 C14 1.397(9) .
C1 Cl1 1.755(9) .
C2 C3 1.363(12) .
C2 H2 0.9300 .
C3 C4 1.353(12) .
C3 H3 0.9300 .
C4 C5 1.450(7) .
C4 H4 0.9300 .
C5 C6 1.357(9) .
C5 C14 1.437(9) .
C6 C7 1.397(7) .
C6 O1 1.437(7) .
C7 C12 1.410(8) .
C7 C8 1.437(8) .
C8 C9 1.315(10) .
C8 H8 0.9300 .
C9 C10 1.452(11) .
C9 H9 0.9300 .
C10 C11 1.348(10) .
C10 H10 0.9300 .
C11 C12 1.426(8) .
C11 Cl2 1.743(7) .
C12 C13 1.391(8) .
C13 C14 1.377(8) .
C13 H13 0.9300 .
O1 S1' 1.585(8) .
O1 S1 1.607(8) .
S1 O2 1.3994(11) .
S1 O3 1.4011(10) .
S1 C15 1.873(13) .
C15 F1 1.3197(11) .
C15 F2 1.3198(11) .
C15 F3 1.3199(11) .
S1' O2' 1.3994(10) .
S1' O3' 1.3999(10) .
S1' C15' 1.700(12) .
C15' F2' 1.3201(11) .
C15' F1' 1.3201(11) .
C15' F3' 1.3201(10) .
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 0.4(10) . . . .
Cl1 C1 C2 C3 -178.4(5) . . . .
C1 C2 C3 C4 -0.7(11) . . . .
C2 C3 C4 C5 1.3(10) . . . .
C3 C4 C5 C6 179.9(5) . . . .
C3 C4 C5 C14 -1.5(8) . . . .
C14 C5 C6 C7 -1.8(8) . . . .
C4 C5 C6 C7 176.7(5) . . . .
C14 C5 C6 O1 -177.2(4) . . . .
C4 C5 C6 O1 1.4(8) . . . .
C5 C6 C7 C12 2.1(8) . . . .
O1 C6 C7 C12 177.5(4) . . . .
C5 C6 C7 C8 -177.7(5) . . . .
O1 C6 C7 C8 -2.2(7) . . . .
C6 C7 C8 C9 179.5(6) . . . .
C12 C7 C8 C9 -0.3(9) . . . .
C7 C8 C9 C10 2.8(11) . . . .
C8 C9 C10 C11 -4.1(11) . . . .
C9 C10 C11 C12 2.9(10) . . . .
C9 C10 C11 Cl2 -176.9(5) . . . .
C6 C7 C12 C13 -1.9(7) . . . .
C8 C7 C12 C13 177.9(5) . . . .
C6 C7 C12 C11 179.3(4) . . . .
C8 C7 C12 C11 -0.9(7) . . . .
C10 C11 C12 C13 -179.3(5) . . . .
Cl2 C11 C12 C13 0.6(7) . . . .
C10 C11 C12 C7 -0.5(8) . . . .
Cl2 C11 C12 C7 179.3(3) . . . .
C7 C12 C13 C14 1.6(8) . . . .
C11 C12 C13 C14 -179.7(5) . . . .
C12 C13 C14 C1 -179.7(5) . . . .
C12 C13 C14 C5 -1.2(8) . . . .
C2 C1 C14 C13 177.8(6) . . . .
Cl1 C1 C14 C13 -3.4(7) . . . .
C2 C1 C14 C5 -0.7(8) . . . .
Cl1 C1 C14 C5 178.1(4) . . . .
C6 C5 C14 C13 1.3(7) . . . .
C4 C5 C14 C13 -177.4(5) . . . .
C6 C5 C14 C1 179.9(4) . . . .
C4 C5 C14 C1 1.2(7) . . . .
C5 C6 O1 S1' -74.2(6) . . . .
C7 C6 O1 S1' 110.0(5) . . . .
C5 C6 O1 S1 -97.7(6) . . . .
C7 C6 O1 S1 86.6(5) . . . .
C6 O1 S1 O2 -27.1(8) . . . .
S1' O1 S1 O2 -128.9(17) . . . .
C6 O1 S1 O3 92.7(7) . . . .
S1' O1 S1 O3 -9.1(13) . . . .
C6 O1 S1 C15 -164.9(6) . . . .
S1' O1 S1 C15 93.3(15) . . . .
O2 S1 C15 F1 -46.4(14) . . . .
O3 S1 C15 F1 -160.2(12) . . . .
O1 S1 C15 F1 86.0(12) . . . .
O2 S1 C15 F2 -168.7(11) . . . .
O3 S1 C15 F2 77.6(10) . . . .
O1 S1 C15 F2 -36.3(10) . . . .
O2 S1 C15 F3 74.0(11) . . . .
O3 S1 C15 F3 -39.8(12) . . . .
O1 S1 C15 F3 -153.6(11) . . . .
C6 O1 S1' O2' -21.9(9) . . . .
S1 O1 S1' O2' 67.9(13) . . . .
C6 O1 S1' O3' 98.7(7) . . . .
S1 O1 S1' O3' -171.6(17) . . . .
C6 O1 S1' C15' -137.7(5) . . . .
S1 O1 S1' C15' -47.9(13) . . . .
O2' S1' C15' F2' -163.8(8) . . . .
O3' S1' C15' F2' 78.8(9) . . . .
O1 S1' C15' F2' -48.3(6) . . . .
O2' S1' C15' F1' -45.3(9) . . . .
O3' S1' C15' F1' -162.7(9) . . . .
O1 S1' C15' F1' 70.2(7) . . . .
O2' S1' C15' F3' 73.7(8) . . . .
O3' S1' C15' F3' -43.8(8) . . . .
O1 S1' C15' F3' -170.8(5) . . . .
