#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:01:59 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301802 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/86/2108600.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2108600
loop_
_publ_author_name
'Moliterni, Anna'
'Altamura, Davide'
'Lassandro, Rocco'
'Olieric, Vincent'
'Ferri, Gianmarco'
'Cardarelli, Francesco'
'Camposeo, Andrea'
'Pisignano, Dario'
'Anthony, John E.'
'Giannini, Cinzia'
_publ_section_title
;
 Synthesis, crystal structure, polymorphism and microscopic luminescence
 properties of anthracene derivative compounds
;
_journal_coeditor_code           RA5074
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2052520620004424
_journal_volume                  76
_journal_year                    2020
_chemical_formula_moiety         'C24 H22 F4 Si2'
_chemical_formula_sum            'C24 H22 F4 Si2'
_chemical_formula_weight         442.59
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-05-14 # Formatted by publCIF
;
_cell_angle_alpha                90
_cell_angle_beta                 94.82(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.9050(14)
_cell_length_b                   14.948(3)
_cell_length_c                   23.660(5)
_cell_measurement_reflns_used    421
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.754
_cell_measurement_theta_min      1.655
_cell_volume                     2433.5(9)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'multi-axis PRIGo goniometer'
_diffrn_measurement_method
'ω scans, shutterless continuous rotation method'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.72932
_diffrn_reflns_av_R_equivalents  0.0592
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            62204
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.950
_diffrn_reflns_theta_max         26.754
_diffrn_reflns_theta_min         1.655
_diffrn_standards_decay_%        0.5
_diffrn_standards_interval_time  0.00167
_diffrn_standards_number         4807
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_description       needle
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.0125
_exptl_crystal_size_min          0.0125
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         4807
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0739
_refine_ls_R_factor_gt           0.0480
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0702P)²+0.5392P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1264
_refine_ls_wR_factor_ref         0.1480
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3237
_reflns_number_total             4807
_reflns_threshold_expression     'I > 2σ(I)'
_publcif_info_exptl_table_max_cols 4
_publcif_info_exptl_table_use_headnotes n
_cod_data_source_file            ra5074sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        2433.5(8)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2108600
_cod_database_fobs_code          2108600
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Si1 Si 0.77925(12) 0.84835(5) 0.22633(4) 0.0897(3) Uani 1 1 d . . . . .
Si2 Si 0.64819(16) 1.45054(5) -0.09270(4) 0.1057(3) Uani 1 1 d . . . . .
F1 F 0.7797(2) 0.80384(8) -0.00591(6) 0.0807(4) Uani 1 1 d . . . . .
F2 F 0.7872(2) 0.77163(10) -0.11865(7) 0.1013(5) Uani 1 1 d . . . . .
F3 F 0.7719(3) 0.90604(13) -0.19354(6) 0.1106(6) Uani 1 1 d . . . . .
F4 F 0.7492(2) 1.07801(10) -0.15848(6) 0.0898(4) Uani 1 1 d . . . . .
C1 C 0.7337(3) 1.08694(14) 0.11365(9) 0.0595(5) Uani 1 1 d . . . . .
C2 C 0.7382(3) 1.06734(12) 0.05430(8) 0.0527(4) Uani 1 1 d . . . . .
C3 C 0.7522(3) 0.97987(12) 0.03488(8) 0.0536(5) Uani 1 1 d . . . . .
H3 H 0.7581 0.9331 0.0609 0.064 Uiso 1 1 calc R U . . .
C4 C 0.7576(3) 0.96084(12) -0.02229(9) 0.0539(5) Uani 1 1 d . . . . .
C5 C 0.7715(3) 0.87214(14) -0.04318(10) 0.0636(5) Uani 1 1 d . . . . .
C6 C 0.7754(3) 0.85560(16) -0.09880(12) 0.0739(6) Uani 1 1 d . . . . .
C7 C 0.7679(4) 0.92591(19) -0.13812(10) 0.0771(6) Uani 1 1 d . . . . .
C8 C 0.7559(3) 1.01123(17) -0.12058(9) 0.0685(6) Uani 1 1 d . . . . .
C9 C 0.7493(3) 1.03292(14) -0.06245(9) 0.0569(5) Uani 1 1 d . . . . .
C10 C 0.7343(3) 1.12031(13) -0.04307(9) 0.0595(5) Uani 1 1 d . . . . .
H10 H 0.7281 1.1671 -0.0691 0.071 Uiso 1 1 calc R U . . .
C11 C 0.7283(3) 1.13933(12) 0.01422(9) 0.0558(5) Uani 1 1 d . . . . .
C12 C 0.7119(3) 1.22989(13) 0.03469(10) 0.0669(6) Uani 1 1 d . . . . .
C13 C 0.7098(4) 1.24464(15) 0.09152(12) 0.0770(6) Uani 1 1 d . . . . .
H13 H 0.7008 1.3031 0.1045 0.092 Uiso 1 1 calc R U . . .
C14 C 0.7207(3) 1.17456(15) 0.13110(11) 0.0717(6) Uani 1 1 d . . . . .
H14 H 0.7193 1.1874 0.1695 0.086 Uiso 1 1 calc R U . . .
C15 C 0.7448(3) 1.01472(15) 0.15357(9) 0.0633(5) Uani 1 1 d . . . . .
C16 C 0.7560(3) 0.95084(16) 0.18430(10) 0.0714(6) Uani 1 1 d . . . . .
C17 C 0.9936(5) 0.8601(3) 0.27760(17) 0.1577(19) Uani 1 1 d . . . . .
H17A H 1.0110 0.8063 0.2996 0.237 Uiso 1 1 calc R U . . .
H17B H 0.9748 0.9097 0.3024 0.237 Uiso 1 1 calc R U . . .
H17C H 1.1068 0.8705 0.2576 0.237 Uiso 1 1 calc R U . . .
C18 C 0.5596(4) 0.8325(3) 0.26395(16) 0.1257(13) Uani 1 1 d . . . . .
H18A H 0.5786 0.7832 0.2898 0.189 Uiso 1 1 calc R U . . .
H18B H 0.4511 0.8203 0.2370 0.189 Uiso 1 1 calc R U . . .
H18C H 0.5345 0.8859 0.2847 0.189 Uiso 1 1 calc R U . . .
C19 C 0.8126(9) 0.7584(3) 0.1759(2) 0.200(3) Uani 1 1 d . . . . .
H19A H 0.8515 0.7049 0.1962 0.300 Uiso 1 1 calc R U . . .
H19B H 0.9112 0.7752 0.1517 0.300 Uiso 1 1 calc R U . . .
H19C H 0.6926 0.7479 0.1534 0.300 Uiso 1 1 calc R U . . .
C20 C 0.6958(4) 1.30201(14) -0.00519(12) 0.0808(7) Uani 1 1 d . . . . .
C21 C 0.6799(5) 1.36126(16) -0.03916(14) 0.0945(8) Uani 1 1 d . . . . .
C22 C 0.3877(6) 1.4793(3) -0.10196(18) 0.1435(15) Uani 1 1 d . . . . .
H22A H 0.3630 1.5156 -0.1353 0.215 Uiso 1 1 calc R U . . .
H22B H 0.3524 1.5118 -0.0694 0.215 Uiso 1 1 calc R U . . .
H22C H 0.3121 1.4254 -0.1061 0.215 Uiso 1 1 calc R U . . .
C23 C 0.7880(8) 1.5485(2) -0.06689(19) 0.1564(17) Uani 1 1 d . . . . .
H23A H 0.7752 1.5950 -0.0950 0.235 Uiso 1 1 calc R U . . .
H23B H 0.9224 1.5325 -0.0598 0.235 Uiso 1 1 calc R U . . .
H23C H 0.7396 1.5695 -0.0324 0.235 Uiso 1 1 calc R U . . .
C24 C 0.7293(8) 1.4056(3) -0.15961(18) 0.1625(18) Uani 1 1 d . . . . .
H24A H 0.6947 1.4468 -0.1900 0.244 Uiso 1 1 calc R U . . .
H24B H 0.6676 1.3490 -0.1679 0.244 Uiso 1 1 calc R U . . .
H24C H 0.8678 1.3978 -0.1557 0.244 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0034 0.0017 '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'
F F 0.0178 0.0109 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0865 0.0750 '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
_geom_angle_publ_flag
C19 Si1 C16 105.79(18) . . ?
C19 Si1 C18 112.1(2) . . ?
C16 Si1 C18 109.48(13) . . ?
C19 Si1 C17 111.3(3) . . ?
C16 Si1 C17 107.91(16) . . ?
C18 Si1 C17 110.11(17) . . ?
C23 Si2 C21 108.76(17) . . ?
C23 Si2 C22 109.6(2) . . ?
C21 Si2 C22 108.01(17) . . ?
C23 Si2 C24 112.8(2) . . ?
C21 Si2 C24 107.39(16) . . ?
C22 Si2 C24 110.2(2) . . ?
C14 C1 C15 121.3(2) . . ?
C14 C1 C2 119.58(19) . . ?
C15 C1 C2 119.09(18) . . ?
C3 C2 C11 119.21(18) . . ?
C3 C2 C1 121.45(17) . . ?
C11 C2 C1 119.34(17) . . ?
C4 C3 C2 121.55(17) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 122.62(18) . . ?
C3 C4 C9 119.30(18) . . ?
C5 C4 C9 118.07(19) . . ?
C6 C5 F1 119.9(2) . . ?
C6 C5 C4 121.4(2) . . ?
F1 C5 C4 118.7(2) . . ?
C5 C6 F2 121.4(2) . . ?
C5 C6 C7 120.7(2) . . ?
F2 C6 C7 117.9(2) . . ?
C8 C7 F3 121.1(2) . . ?
C8 C7 C6 120.4(2) . . ?
F3 C7 C6 118.6(2) . . ?
F4 C8 C7 120.0(2) . . ?
F4 C8 C9 118.5(2) . . ?
C7 C8 C9 121.6(2) . . ?
C10 C9 C8 122.95(19) . . ?
C10 C9 C4 119.14(19) . . ?
C8 C9 C4 117.91(19) . . ?
C11 C10 C9 121.53(18) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C10 C11 C2 119.26(18) . . ?
C10 C11 C12 121.89(18) . . ?
C2 C11 C12 118.86(19) . . ?
C13 C12 C20 121.4(2) . . ?
C13 C12 C11 119.3(2) . . ?
C20 C12 C11 119.3(2) . . ?
C12 C13 C14 122.2(2) . . ?
C12 C13 H13 118.9 . . ?
C14 C13 H13 118.9 . . ?
C1 C14 C13 120.7(2) . . ?
C1 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C16 C15 C1 176.0(2) . . ?
C15 C16 Si1 175.4(2) . . ?
Si1 C17 H17A 109.5 . . ?
Si1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
Si1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
Si1 C18 H18A 109.5 . . ?
Si1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
Si1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
Si1 C19 H19A 109.5 . . ?
Si1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
Si1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C12 178.7(3) . . ?
C20 C21 Si2 178.0(3) . . ?
Si2 C22 H22A 109.5 . . ?
Si2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
Si2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
Si2 C23 H23A 109.5 . . ?
Si2 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
Si2 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
Si2 C24 H24A 109.5 . . ?
Si2 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
Si2 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Si1 C19 1.825(5) . ?
Si1 C16 1.826(2) . ?
Si1 C18 1.837(3) . ?
Si1 C17 1.842(4) . ?
Si2 C23 1.831(4) . ?
Si2 C21 1.841(3) . ?
Si2 C22 1.844(4) . ?
Si2 C24 1.849(4) . ?
F1 C5 1.347(2) . ?
F2 C6 1.345(3) . ?
F3 C7 1.347(3) . ?
F4 C8 1.340(3) . ?
C1 C14 1.378(3) . ?
C1 C15 1.432(3) . ?
C1 C2 1.437(3) . ?
C2 C3 1.392(3) . ?
C2 C11 1.432(3) . ?
C3 C4 1.386(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.421(3) . ?
C4 C9 1.435(3) . ?
C5 C6 1.341(3) . ?
C6 C7 1.402(4) . ?
C7 C8 1.346(3) . ?
C8 C9 1.418(3) . ?
C9 C10 1.391(3) . ?
C10 C11 1.389(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.445(3) . ?
C12 C13 1.364(3) . ?
C12 C20 1.431(3) . ?
C13 C14 1.403(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.199(3) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.195(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 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
_geom_torsion_publ_flag
C14 C1 C2 C3 179.66(19) . . . . ?
C15 C1 C2 C3 0.3(3) . . . . ?
C14 C1 C2 C11 -0.3(3) . . . . ?
C15 C1 C2 C11 -179.63(18) . . . . ?
C11 C2 C3 C4 0.3(3) . . . . ?
C1 C2 C3 C4 -179.67(17) . . . . ?
C2 C3 C4 C5 -179.87(18) . . . . ?
C2 C3 C4 C9 0.3(3) . . . . ?
C3 C4 C5 C6 179.7(2) . . . . ?
C9 C4 C5 C6 -0.5(3) . . . . ?
C3 C4 C5 F1 0.0(3) . . . . ?
C9 C4 C5 F1 179.88(17) . . . . ?
F1 C5 C6 F2 0.1(3) . . . . ?
C4 C5 C6 F2 -179.55(19) . . . . ?
F1 C5 C6 C7 -179.7(2) . . . . ?
C4 C5 C6 C7 0.7(4) . . . . ?
C5 C6 C7 C8 -0.2(4) . . . . ?
F2 C6 C7 C8 180.0(2) . . . . ?
C5 C6 C7 F3 -179.9(2) . . . . ?
F2 C6 C7 F3 0.3(3) . . . . ?
F3 C7 C8 F4 -0.5(3) . . . . ?
C6 C7 C8 F4 179.9(2) . . . . ?
F3 C7 C8 C9 179.3(2) . . . . ?
C6 C7 C8 C9 -0.4(4) . . . . ?
F4 C8 C9 C10 0.7(3) . . . . ?
C7 C8 C9 C10 -179.1(2) . . . . ?
F4 C8 C9 C4 -179.70(17) . . . . ?
C7 C8 C9 C4 0.5(3) . . . . ?
C3 C4 C9 C10 -0.6(3) . . . . ?
C5 C4 C9 C10 179.53(18) . . . . ?
C3 C4 C9 C8 179.75(18) . . . . ?
C5 C4 C9 C8 -0.1(3) . . . . ?
C8 C9 C10 C11 -179.96(19) . . . . ?
C4 C9 C10 C11 0.4(3) . . . . ?
C9 C10 C11 C2 0.1(3) . . . . ?
C9 C10 C11 C12 -179.77(19) . . . . ?
C3 C2 C11 C10 -0.4(3) . . . . ?
C1 C2 C11 C10 179.48(17) . . . . ?
C3 C2 C11 C12 179.43(18) . . . . ?
C1 C2 C11 C12 -0.6(3) . . . . ?
C10 C11 C12 C13 -179.0(2) . . . . ?
C2 C11 C12 C13 1.1(3) . . . . ?
C10 C11 C12 C20 1.8(3) . . . . ?
C2 C11 C12 C20 -178.1(2) . . . . ?
C20 C12 C13 C14 178.4(2) . . . . ?
C11 C12 C13 C14 -0.8(4) . . . . ?
C15 C1 C14 C13 -180.0(2) . . . . ?
C2 C1 C14 C13 0.7(3) . . . . ?
C12 C13 C14 C1 -0.2(4) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168308500
