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#$Date: 2023-07-05 00:55:10 +0300 (Wed, 05 Jul 2023) $
#$Revision: 284777 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/18/7131830.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_7131830
loop_
_publ_author_name
'Zhao, Yu-Qiang'
'Zhu, Liping'
'Lu, Jian-Mei'
'Yu, Le'
'Zhang, Lanyun'
'Zhou, Ying'
_publ_section_title
;
 New charge transfer-based organic room temperature phosphorescent trace
 doping systems.
;
_journal_issue                   54
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              8396
_journal_page_last               8399
_journal_paper_doi               10.1039/d3cc02386a
_journal_volume                  59
_journal_year                    2023
_chemical_formula_sum            'C15 H8 F6 N2 S'
_chemical_formula_weight         362.29
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2021-06-26 deposited with the CCDC.	2023-06-09 downloaded from the CCDC.
;
_cell_angle_alpha                102.4300(10)
_cell_angle_beta                 109.290(2)
_cell_angle_gamma                107.080(2)
_cell_formula_units_Z            2
_cell_length_a                   8.5804(3)
_cell_length_b                   9.4893(4)
_cell_length_c                   10.4129(4)
_cell_measurement_reflns_used    9944
_cell_measurement_temperature    302(2)
_cell_measurement_theta_max      68.5712
_cell_measurement_theta_min      4.7959
_cell_volume                     717.67(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      302(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-III D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0560
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16178
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.565
_diffrn_reflns_theta_min         4.796
_diffrn_source                   sadabs
_exptl_absorpt_coefficient_mu    2.691
_exptl_absorpt_correction_T_max  0.650
_exptl_absorpt_correction_T_min  0.550
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            PINK
_exptl_crystal_density_diffrn    1.677
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.160
_refine_diff_density_max         1.066
_refine_diff_density_min         -0.752
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2621
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0882
_refine_ls_R_factor_gt           0.0806
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1375P)²+0.9384P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2296
_refine_ls_wR_factor_ref         0.2403
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2282
_reflns_number_total             2621
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc02386a2.cif
_cod_data_source_block           1_CCDC2
_cod_database_code               7131830
_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.
;
_shelx_estimated_absorpt_t_min   0.480
_shelx_estimated_absorpt_t_max   0.673
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
C1 C 0.4296(5) 1.2119(4) 0.3820(4) 0.0461(8) Uani 1 1 d . . . . .
H1 H 0.4692 1.3207 0.4170 0.055 Uiso 1 1 calc R U . . .
C2 C 0.4874(5) 1.1393(4) 0.2878(4) 0.0450(8) Uani 1 1 d . . . . .
C3 C 0.4288(5) 0.9774(4) 0.2362(4) 0.0436(8) Uani 1 1 d . . . . .
H3 H 0.4700 0.9313 0.1733 0.052 Uiso 1 1 calc R U . . .
C4 C 0.3094(5) 0.8818(4) 0.2762(4) 0.0411(8) Uani 1 1 d . . . . .
C5 C 0.2518(5) 0.9555(4) 0.3704(4) 0.0439(8) Uani 1 1 d . . . . .
H5 H 0.1719 0.8951 0.3991 0.053 Uiso 1 1 calc R U . . .
C6 C 0.3113(5) 1.1183(4) 0.4227(4) 0.0456(8) Uani 1 1 d . . . . .
C7 C 0.2471(6) 1.1937(5) 0.5247(5) 0.0541(10) Uani 1 1 d . . . . .
C8 C 0.6209(6) 1.2377(5) 0.2470(5) 0.0540(10) Uani 1 1 d . . . . .
C9 C 0.2507(5) 0.7070(4) 0.2214(4) 0.0410(8) Uani 1 1 d . . . . .
C10 C 0.2750(5) 0.6343(4) 0.1029(4) 0.0454(8) Uani 1 1 d . . . . .
H10 H 0.3234 0.6931 0.0542 0.054 Uiso 1 1 calc R U . . .
C11 C 0.2262(5) 0.4726(4) 0.0581(4) 0.0428(8) Uani 1 1 d . . . . .
C12 C 0.1480(5) 0.3794(4) 0.1258(4) 0.0431(8) Uani 1 1 d . . . . .
C13 C 0.1240(6) 0.4531(5) 0.2434(4) 0.0507(9) Uani 1 1 d . . . . .
H13 H 0.0740 0.3944 0.2914 0.061 Uiso 1 1 calc R U . . .
C14 C 0.1744(5) 0.6137(4) 0.2894(4) 0.0474(9) Uani 1 1 d . . . . .
H14 H 0.1570 0.6616 0.3684 0.057 Uiso 1 1 calc R U . . .
C15 C 0.1486(5) 0.1905(4) -0.0412(4) 0.0455(8) Uani 1 1 d . . . . .
F1 F 0.6277(10) 1.1655(4) 0.1322(6) 0.180(3) Uani 1 1 d . . . . .
F2 F 0.7769(5) 1.2929(10) 0.3419(6) 0.227(4) Uani 1 1 d . . . . .
F3 F 0.5903(8) 1.3536(5) 0.2195(7) 0.151(2) Uani 1 1 d . . . . .
F4 F 0.3435(5) 1.3441(4) 0.5935(4) 0.1052(13) Uani 1 1 d . . . . .
F5 F 0.0783(4) 1.1779(5) 0.4572(4) 0.0941(11) Uani 1 1 d . . . . .
F6 F 0.2478(5) 1.1300(4) 0.6267(3) 0.0892(10) Uani 1 1 d . . . . .
N1 N 0.1045(4) 0.2195(4) 0.0673(3) 0.0473(7) Uani 1 1 d . . . . .
N2 N 0.1274(5) 0.0476(4) -0.1161(4) 0.0589(9) Uani 1 1 d . . . . .
H2A H 0.0823 -0.0321 -0.0938 0.071 Uiso 1 1 calc R U . . .
H2B H 0.1590 0.0353 -0.1867 0.071 Uiso 1 1 calc R U . . .
S1 S 0.24578(14) 0.35421(10) -0.08407(10) 0.0526(4) 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 0.0181 0.0091 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
C2 C1 C6 118.3(3) . . ?
C2 C1 H1 120.9 . . ?
C6 C1 H1 120.9 . . ?
C1 C2 C3 120.8(3) . . ?
C1 C2 C8 119.4(3) . . ?
C3 C2 C8 119.8(3) . . ?
C2 C3 C4 121.5(3) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 117.3(3) . . ?
C5 C4 C9 122.1(3) . . ?
C3 C4 C9 120.6(3) . . ?
C4 C5 C6 121.1(3) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 121.0(3) . . ?
C1 C6 C7 119.4(3) . . ?
C5 C6 C7 119.6(3) . . ?
F4 C7 F6 106.0(4) . . ?
F4 C7 F5 106.6(4) . . ?
F6 C7 F5 105.4(4) . . ?
F4 C7 C6 113.7(4) . . ?
F6 C7 C6 112.5(3) . . ?
F5 C7 C6 112.1(3) . . ?
F2 C8 F3 106.2(6) . . ?
F2 C8 F1 105.1(6) . . ?
F3 C8 F1 102.7(5) . . ?
F2 C8 C2 113.0(4) . . ?
F3 C8 C2 114.3(4) . . ?
F1 C8 C2 114.5(4) . . ?
C10 C9 C14 118.4(3) . . ?
C10 C9 C4 120.4(3) . . ?
C14 C9 C4 121.1(3) . . ?
C9 C10 C11 119.2(3) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 H10 120.4 . . ?
C10 C11 C12 122.1(3) . . ?
C10 C11 S1 128.3(3) . . ?
C12 C11 S1 109.6(3) . . ?
N1 C12 C13 126.5(3) . . ?
N1 C12 C11 115.3(3) . . ?
C13 C12 C11 118.2(3) . . ?
C14 C13 C12 119.9(3) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C9 122.2(3) . . ?
C13 C14 H14 118.9 . . ?
C9 C14 H14 118.9 . . ?
N1 C15 N2 124.0(3) . . ?
N1 C15 S1 116.0(3) . . ?
N2 C15 S1 120.0(3) . . ?
C15 N1 C12 110.5(3) . . ?
C15 N2 H2A 120.0 . . ?
C15 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C11 S1 C15 88.60(17) . . ?
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
C1 C2 1.383(5) . ?
C1 C6 1.384(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.383(5) . ?
C2 C8 1.493(5) . ?
C3 C4 1.395(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.388(5) . ?
C4 C9 1.497(5) . ?
C5 C6 1.391(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.495(5) . ?
C7 F4 1.307(5) . ?
C7 F6 1.329(5) . ?
C7 F5 1.330(5) . ?
C8 F2 1.239(6) . ?
C8 F3 1.271(6) . ?
C8 F1 1.272(5) . ?
C9 C10 1.389(5) . ?
C9 C14 1.397(5) . ?
C10 C11 1.391(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.400(5) . ?
C11 S1 1.743(4) . ?
C12 N1 1.390(5) . ?
C12 C13 1.383(5) . ?
C13 C14 1.379(5) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 N1 1.306(5) . ?
C15 N2 1.337(5) . ?
C15 S1 1.758(4) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2B F6 0.86 2.55 3.333(5) 152.1 1_544
N2 H2A N1 0.86 2.15 2.984(5) 162.3 2
N2 H2A N1 0.86 2.15 2.984(5) 162.3 2
N2 H2B F6 0.86 2.55 3.333(5) 152.1 1_544
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
C6 C1 C2 C3 -0.2(6) . . . . ?
C6 C1 C2 C8 -177.5(4) . . . . ?
C1 C2 C3 C4 0.3(6) . . . . ?
C8 C2 C3 C4 177.6(4) . . . . ?
C2 C3 C4 C5 -0.1(5) . . . . ?
C2 C3 C4 C9 -178.7(3) . . . . ?
C3 C4 C5 C6 -0.1(5) . . . . ?
C9 C4 C5 C6 178.5(3) . . . . ?
C2 C1 C6 C5 -0.1(6) . . . . ?
C2 C1 C6 C7 179.8(4) . . . . ?
C4 C5 C6 C1 0.2(6) . . . . ?
C4 C5 C6 C7 -179.6(3) . . . . ?
C1 C6 C7 F4 -15.8(6) . . . . ?
C5 C6 C7 F4 164.0(4) . . . . ?
C1 C6 C7 F6 -136.3(4) . . . . ?
C5 C6 C7 F6 43.6(5) . . . . ?
C1 C6 C7 F5 105.2(4) . . . . ?
C5 C6 C7 F5 -75.0(5) . . . . ?
C1 C2 C8 F2 78.7(7) . . . . ?
C3 C2 C8 F2 -98.6(7) . . . . ?
C1 C2 C8 F3 -42.9(6) . . . . ?
C3 C2 C8 F3 139.8(5) . . . . ?
C1 C2 C8 F1 -161.0(5) . . . . ?
C3 C2 C8 F1 21.7(7) . . . . ?
C5 C4 C9 C10 164.8(3) . . . . ?
C3 C4 C9 C10 -16.7(5) . . . . ?
C5 C4 C9 C14 -16.7(6) . . . . ?
C3 C4 C9 C14 161.8(4) . . . . ?
C14 C9 C10 C11 -1.3(6) . . . . ?
C4 C9 C10 C11 177.3(3) . . . . ?
C9 C10 C11 C12 2.0(6) . . . . ?
C9 C10 C11 S1 -178.9(3) . . . . ?
C10 C11 C12 N1 179.2(3) . . . . ?
S1 C11 C12 N1 -0.1(4) . . . . ?
C10 C11 C12 C13 -1.8(6) . . . . ?
S1 C11 C12 C13 178.9(3) . . . . ?
N1 C12 C13 C14 179.8(4) . . . . ?
C11 C12 C13 C14 0.9(6) . . . . ?
C12 C13 C14 C9 -0.3(6) . . . . ?
C10 C9 C14 C13 0.4(6) . . . . ?
C4 C9 C14 C13 -178.1(4) . . . . ?
N2 C15 N1 C12 178.1(4) . . . . ?
S1 C15 N1 C12 -0.5(4) . . . . ?
C13 C12 N1 C15 -178.6(4) . . . . ?
C11 C12 N1 C15 0.3(5) . . . . ?
C10 C11 S1 C15 -179.3(4) . . . . ?
C12 C11 S1 C15 -0.2(3) . . . . ?
N1 C15 S1 C11 0.4(3) . . . . ?
N2 C15 S1 C11 -178.2(3) . . . . ?
