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#$Date: 2023-05-05 04:00:41 +0300 (Fri, 05 May 2023) $
#$Revision: 283158 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/82/1568226.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_1568226
loop_
_publ_author_name
'Shen, Shen'
'Baryshnikov, Glib V.'
'Xie, Qishan'
'Wu, Bin'
'Lv, Meng'
'Sun, Hao'
'Li, Zhongyu'
'Ågren, Hans'
'Chen, Jinquan'
'Zhu, Liangliang'
_publ_section_title
;
 Making multi-twisted luminophores produce persistent room-temperature
 phosphorescence.
;
_journal_issue                   4
_journal_name_full               'Chemical science'
_journal_page_first              970
_journal_page_last               978
_journal_paper_doi               10.1039/d2sc05741g
_journal_volume                  14
_journal_year                    2023
_chemical_formula_sum            'C24 H18 F4 O4 S2'
_chemical_formula_weight         510.50
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc2c7cnn
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2022-06-25 deposited with the CCDC.	2023-01-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.329(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.8071(3)
_cell_length_b                   20.6990(14)
_cell_length_c                   11.0964(7)
_cell_measurement_reflns_used    9645
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      54.84
_cell_measurement_theta_min      3.72
_cell_volume                     1097.39(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14089
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.840
_diffrn_reflns_theta_min         3.716
_exptl_absorpt_coefficient_mu    1.825
_exptl_absorpt_correction_T_max  0.816
_exptl_absorpt_correction_T_min  0.534
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_description       rod
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2068
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0367
_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)+(0.0639P)²+0.4297P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1053
_refine_ls_wR_factor_ref         0.1076
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1911
_reflns_number_total             2068
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc05741g7.cif
_cod_data_source_block           ga_210901b_a
_cod_depositor_comments
'Adding full bibliography for 1568224--1568235.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1568226
_shelx_shelxl_version_number     2016/6
_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. 
;
_shelx_estimated_absorpt_t_min   0.629
_shelx_estimated_absorpt_t_max   0.914
loop_
_space_group_symop_operation_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_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
S1 S -0.21342(9) 0.40881(2) 0.70091(4) 0.02846(17) Uani 1 1 d . . . . .
F1 F 0.2583(2) 0.50417(5) 0.72965(9) 0.0337(3) Uani 1 1 d . . . . .
F2 F 0.4297(2) 0.58252(5) 0.56273(10) 0.0340(3) Uani 1 1 d . . . . .
O1 O 0.6138(3) 0.15509(6) 0.60949(10) 0.0303(3) Uani 1 1 d . . . . .
O2 O 0.5388(3) 0.13555(6) 0.80170(11) 0.0361(3) Uani 1 1 d . . . . .
C1 C -0.0911(3) 0.45845(8) 0.58847(14) 0.0236(3) Uani 1 1 d . . . . .
C2 C 0.1282(4) 0.50145(8) 0.61618(14) 0.0248(4) Uani 1 1 d . . . . .
C3 C 0.2176(3) 0.54197(7) 0.53039(14) 0.0244(3) Uani 1 1 d . . . . .
C4 C -0.0036(3) 0.33854(8) 0.69361(14) 0.0232(3) Uani 1 1 d . . . . .
C5 C 0.1434(4) 0.32333(8) 0.59683(14) 0.0271(4) Uani 1 1 d . . . . .
H5 H 0.133105 0.350722 0.527790 0.033 Uiso 1 1 calc R U . . .
C6 C 0.3057(4) 0.26783(8) 0.60149(14) 0.0270(4) Uani 1 1 d . . . . .
H6 H 0.407615 0.257531 0.535403 0.032 Uiso 1 1 calc R U . . .
C7 C 0.3213(3) 0.22711(8) 0.70133(14) 0.0237(4) Uani 1 1 d . . . . .
C8 C 0.1681(4) 0.24208(9) 0.79671(15) 0.0322(4) Uani 1 1 d . . . . .
H8 H 0.173761 0.213978 0.864630 0.039 Uiso 1 1 calc R U . . .
C9 C 0.0077(4) 0.29750(9) 0.79345(16) 0.0324(4) Uani 1 1 d . . . . .
H9 H -0.095074 0.307643 0.859350 0.039 Uiso 1 1 calc R U . . .
C10 C 0.4999(3) 0.16812(8) 0.71132(14) 0.0250(4) Uani 1 1 d . . . . .
C11 C 0.7985(4) 0.09917(9) 0.61566(17) 0.0345(4) Uani 1 1 d . . . . .
H11A H 0.691162 0.059259 0.627285 0.041 Uiso 1 1 calc R U . . .
H11B H 0.946524 0.103598 0.684627 0.041 Uiso 1 1 calc R U . . .
C12 C 0.9265(5) 0.09592(10) 0.49874(19) 0.0438(5) Uani 1 1 d . . . . .
H12A H 0.781313 0.085504 0.432503 0.066 Uiso 1 1 calc R U . . .
H12B H 1.071149 0.062367 0.504336 0.066 Uiso 1 1 calc R U . . .
H12C H 1.010621 0.137752 0.482852 0.066 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 0.0137 0.0067 '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 0.0583 0.0400 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2925 0.4295 '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
C1 S1 C4 102.06(7) . . ?
C10 O1 C11 115.17(13) . . ?
C2 C1 C3 117.14(15) . 3_566 ?
C2 C1 S1 121.36(12) . . ?
C3 C1 S1 121.45(13) 3_566 . ?
F1 C2 C3 118.37(15) . . ?
F1 C2 C1 119.86(15) . . ?
C3 C2 C1 121.77(15) . . ?
F2 C3 C2 118.98(14) . . ?
F2 C3 C1 119.92(15) . 3_566 ?
C2 C3 C1 121.10(15) . 3_566 ?
C5 C4 C9 119.98(15) . . ?
C5 C4 S1 124.20(12) . . ?
C9 C4 S1 115.82(13) . . ?
C4 C5 C6 119.50(15) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C5 C6 C7 120.92(15) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C6 C7 C8 119.10(15) . . ?
C6 C7 C10 122.50(15) . . ?
C8 C7 C10 118.40(14) . . ?
C9 C8 C7 120.45(15) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C4 120.03(16) . . ?
C8 C9 H9 120.0 . . ?
C4 C9 H9 120.0 . . ?
O2 C10 O1 123.38(15) . . ?
O2 C10 C7 123.73(15) . . ?
O1 C10 C7 112.89(13) . . ?
O1 C11 C12 107.56(14) . . ?
O1 C11 H11A 110.2 . . ?
C12 C11 H11A 110.2 . . ?
O1 C11 H11B 110.2 . . ?
C12 C11 H11B 110.2 . . ?
H11A C11 H11B 108.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
S1 C1 1.7662(16) . ?
S1 C4 1.7770(17) . ?
F1 C2 1.3439(18) . ?
F2 C3 1.3388(19) . ?
O1 C10 1.336(2) . ?
O1 C11 1.456(2) . ?
O2 C10 1.206(2) . ?
C1 C2 1.388(2) . ?
C1 C3 1.390(2) 3_566 ?
C2 C3 1.373(2) . ?
C4 C5 1.385(2) . ?
C4 C9 1.392(2) . ?
C5 C6 1.386(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.387(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.389(2) . ?
C7 C10 1.490(2) . ?
C8 C9 1.381(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C11 C12 1.497(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
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
C4 S1 C1 C2 -90.35(14) . . . . ?
C4 S1 C1 C3 92.32(14) . . . 3_566 ?
C3 C1 C2 F1 179.85(14) 3_566 . . . ?
S1 C1 C2 F1 2.4(2) . . . . ?
C3 C1 C2 C3 0.0(3) 3_566 . . . ?
S1 C1 C2 C3 -177.47(12) . . . . ?
F1 C2 C3 F2 -0.1(2) . . . . ?
C1 C2 C3 F2 179.82(14) . . . . ?
F1 C2 C3 C1 -179.85(14) . . . 3_566 ?
C1 C2 C3 C1 0.0(3) . . . 3_566 ?
C1 S1 C4 C5 -17.64(16) . . . . ?
C1 S1 C4 C9 162.42(13) . . . . ?
C9 C4 C5 C6 -1.4(2) . . . . ?
S1 C4 C5 C6 178.70(13) . . . . ?
C4 C5 C6 C7 0.5(3) . . . . ?
C5 C6 C7 C8 1.0(3) . . . . ?
C5 C6 C7 C10 -178.12(15) . . . . ?
C6 C7 C8 C9 -1.5(3) . . . . ?
C10 C7 C8 C9 177.62(17) . . . . ?
C7 C8 C9 C4 0.6(3) . . . . ?
C5 C4 C9 C8 0.8(3) . . . . ?
S1 C4 C9 C8 -179.22(15) . . . . ?
C11 O1 C10 O2 -1.9(2) . . . . ?
C11 O1 C10 C7 177.91(14) . . . . ?
C6 C7 C10 O2 172.37(17) . . . . ?
C8 C7 C10 O2 -6.7(3) . . . . ?
C6 C7 C10 O1 -7.4(2) . . . . ?
C8 C7 C10 O1 173.46(15) . . . . ?
C10 O1 C11 C12 -174.68(16) . . . . ?
