#------------------------------------------------------------------------------
#$Date: 2023-07-05 00:55:10 +0300 (Wed, 05 Jul 2023) $
#$Revision: 284777 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/18/7131832.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_7131832
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            'C25 H17 N3 S'
_chemical_formula_weight         391.47
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-09-09 deposited with the CCDC.	2023-06-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.7500(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.7111(3)
_cell_length_b                   8.8354(3)
_cell_length_c                   21.0030(7)
_cell_measurement_reflns_used    9983
_cell_measurement_temperature    301(2)
_cell_measurement_theta_max      28.2788
_cell_measurement_theta_min      2.5090
_cell_volume                     1946.01(11)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_publication_material  'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      301(2)
_diffrn_detector_area_resol_mean 'phi and omega scans'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  graphite
_diffrn_measurement_method       'CCD area detector'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0825
_diffrn_reflns_av_unetI/netI     0.0540
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            24916
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.147
_diffrn_reflns_theta_max         25.147
_diffrn_reflns_theta_min         1.992
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_correction_T_min  0.957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3475
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0465
_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)+(0.0589P)²+0.6799P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1147
_refine_ls_wR_factor_ref         0.1320
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2595
_reflns_number_total             3475
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc02386a2.cif
_cod_data_source_block           1_CCDC4
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7131832
_shelx_shelxl_version_number     2018/3
_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   0.957
_shelx_estimated_absorpt_t_max   0.971
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 0.34271(6) 0.06155(8) 0.08893(4) 0.0574(2) Uani 1 1 d . . . . .
N1 N 0.1499(2) -0.1195(2) 0.03207(11) 0.0578(6) Uani 1 1 d . . . . .
H1A H 0.071881 -0.139285 0.014504 0.069 Uiso 1 1 calc R U . . .
H1B H 0.206571 -0.189697 0.036082 0.069 Uiso 1 1 calc R U . . .
N2 N 0.62296(17) 0.9206(2) 0.30394(9) 0.0478(5) Uani 1 1 d . . . . .
N3 N 0.10372(16) 0.1336(2) 0.04903(9) 0.0417(5) Uani 1 1 d . . . . .
C1 C 0.1832(2) 0.0207(3) 0.05317(11) 0.0452(6) Uani 1 1 d . . . . .
C2 C 0.2977(2) 0.2483(3) 0.09929(11) 0.0420(5) Uani 1 1 d . . . . .
C3 C 0.3712(2) 0.3673(3) 0.12820(11) 0.0437(5) Uani 1 1 d . . . . .
H15 H 0.458114 0.354295 0.144116 0.052 Uiso 1 1 calc R U . . .
C4 C 0.3143(2) 0.5071(3) 0.13339(10) 0.0396(5) Uani 1 1 d . . . . .
C5 C 0.3907(2) 0.6301(3) 0.17072(11) 0.0406(5) Uani 1 1 d . . . . .
C6 C 0.3391(2) 0.7204(3) 0.21285(12) 0.0483(6) Uani 1 1 d . . . . .
H14 H 0.252395 0.714052 0.212741 0.058 Uiso 1 1 calc R U . . .
C7 C 0.4138(2) 0.8190(3) 0.25471(12) 0.0499(6) Uani 1 1 d . . . . .
H13 H 0.377539 0.877692 0.282924 0.060 Uiso 1 1 calc R U . . .
C8 C 0.5425(2) 0.8315(3) 0.25514(11) 0.0442(5) Uani 1 1 d . . . . .
C9 C 0.6009(2) 1.0704(3) 0.31886(11) 0.0435(6) Uani 1 1 d . . . . .
C10 C 0.5233(2) 1.1765(3) 0.28209(13) 0.0547(6) Uani 1 1 d . . . . .
H12 H 0.474628 1.152187 0.241456 0.066 Uiso 1 1 calc R U . . .
C11 C 0.5205(3) 1.3200(3) 0.30778(15) 0.0637(7) Uani 1 1 d . . . . .
H11 H 0.469245 1.393989 0.284060 0.076 Uiso 1 1 calc R U . . .
C12 C 0.5936(3) 1.3556(3) 0.36886(16) 0.0677(8) Uani 1 1 d . . . . .
H1 H 0.588723 1.452418 0.385597 0.081 Uiso 1 1 calc R U . . .
C13 C 0.1659(2) 0.2635(2) 0.07492(10) 0.0381(5) Uani 1 1 d . . . . .
C14 C 0.1838(2) 0.5235(3) 0.10783(10) 0.0397(5) Uani 1 1 d . . . . .
H3 H 0.145632 0.617070 0.110762 0.048 Uiso 1 1 calc R U . . .
C15 C 0.1102(2) 0.4050(3) 0.07838(10) 0.0409(5) Uani 1 1 d . . . . .
H2 H 0.023982 0.419358 0.060971 0.049 Uiso 1 1 calc R U . . .
C16 C 0.5943(2) 0.7501(3) 0.21108(13) 0.0548(7) Uani 1 1 d . . . . .
H4 H 0.679663 0.762421 0.209139 0.066 Uiso 1 1 calc R U . . .
C17 C 0.5189(2) 0.6499(3) 0.16979(12) 0.0537(7) Uani 1 1 d . . . . .
H5 H 0.554855 0.594211 0.140538 0.064 Uiso 1 1 calc R U . . .
C18 C 0.6720(3) 1.2510(3) 0.40448(13) 0.0609(8) Uani 1 1 d . . . . .
H6 H 0.721622 1.277152 0.444638 0.073 Uiso 1 1 calc R U . . .
C19 C 0.6771(2) 1.1048(3) 0.38025(11) 0.0477(6) Uani 1 1 d . . . . .
C20 C 0.7464(2) 0.9699(3) 0.40370(11) 0.0488(6) Uani 1 1 d . . . . .
C21 C 0.7106(2) 0.8583(3) 0.35565(12) 0.0469(6) Uani 1 1 d . . . . .
C22 C 0.7590(2) 0.7127(3) 0.36341(14) 0.0595(7) Uani 1 1 d . . . . .
H7 H 0.734352 0.639158 0.331650 0.071 Uiso 1 1 calc R U . . .
C23 C 0.8454(3) 0.6808(4) 0.42009(16) 0.0715(8) Uani 1 1 d . . . . .
H8 H 0.879133 0.583746 0.426487 0.086 Uiso 1 1 calc R U . . .
C24 C 0.8833(3) 0.7891(4) 0.46773(15) 0.0730(9) Uani 1 1 d . . . . .
H10 H 0.942766 0.764213 0.505017 0.088 Uiso 1 1 calc R U . . .
C25 C 0.8337(2) 0.9336(4) 0.46047(13) 0.0616(8) Uani 1 1 d . . . . .
H9 H 0.858023 1.005594 0.492903 0.074 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 0.0033 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'
N N 0.0061 0.0033 '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
_geom_angle_publ_flag
C2 S1 C1 88.75(11) . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C9 N2 C21 108.57(19) . . ?
C9 N2 C8 125.35(19) . . ?
C21 N2 C8 123.4(2) . . ?
C1 N3 C13 110.72(18) . . ?
N3 C1 N1 124.1(2) . . ?
N3 C1 S1 115.86(17) . . ?
N1 C1 S1 120.07(18) . . ?
C3 C2 C13 121.9(2) . . ?
C3 C2 S1 128.96(18) . . ?
C13 C2 S1 109.09(16) . . ?
C2 C3 C4 119.4(2) . . ?
C2 C3 H15 120.3 . . ?
C4 C3 H15 120.3 . . ?
C3 C4 C14 118.8(2) . . ?
C3 C4 C5 119.2(2) . . ?
C14 C4 C5 121.8(2) . . ?
C6 C5 C17 117.4(2) . . ?
C6 C5 C4 120.60(19) . . ?
C17 C5 C4 121.71(19) . . ?
C7 C6 C5 121.1(2) . . ?
C7 C6 H14 119.4 . . ?
C5 C6 H14 119.4 . . ?
C6 C7 C8 120.4(2) . . ?
C6 C7 H13 119.8 . . ?
C8 C7 H13 119.8 . . ?
C16 C8 C7 119.5(2) . . ?
C16 C8 N2 120.2(2) . . ?
C7 C8 N2 120.2(2) . . ?
C10 C9 N2 129.1(2) . . ?
C10 C9 C19 122.4(2) . . ?
N2 C9 C19 108.5(2) . . ?
C9 C10 C11 117.6(3) . . ?
C9 C10 H12 121.2 . . ?
C11 C10 H12 121.2 . . ?
C10 C11 C12 120.9(3) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C18 C12 C11 121.2(3) . . ?
C18 C12 H1 119.4 . . ?
C11 C12 H1 119.4 . . ?
N3 C13 C15 126.02(19) . . ?
N3 C13 C2 115.57(19) . . ?
C15 C13 C2 118.4(2) . . ?
C15 C14 C4 121.9(2) . . ?
C15 C14 H3 119.0 . . ?
C4 C14 H3 119.0 . . ?
C14 C15 C13 119.5(2) . . ?
C14 C15 H2 120.3 . . ?
C13 C15 H2 120.3 . . ?
C8 C16 C17 119.6(2) . . ?
C8 C16 H4 120.2 . . ?
C17 C16 H4 120.2 . . ?
C16 C17 C5 121.8(2) . . ?
C16 C17 H5 119.1 . . ?
C5 C17 H5 119.1 . . ?
C12 C18 C19 119.5(3) . . ?
C12 C18 H6 120.2 . . ?
C19 C18 H6 120.2 . . ?
C18 C19 C9 118.3(3) . . ?
C18 C19 C20 134.4(2) . . ?
C9 C19 C20 107.3(2) . . ?
C25 C20 C21 119.3(3) . . ?
C25 C20 C19 133.9(3) . . ?
C21 C20 C19 106.8(2) . . ?
C22 C21 N2 129.4(2) . . ?
C22 C21 C20 121.7(2) . . ?
N2 C21 C20 108.9(2) . . ?
C23 C22 C21 117.4(3) . . ?
C23 C22 H7 121.3 . . ?
C21 C22 H7 121.3 . . ?
C22 C23 C24 121.9(3) . . ?
C22 C23 H8 119.0 . . ?
C24 C23 H8 119.0 . . ?
C25 C24 C23 120.7(3) . . ?
C25 C24 H10 119.7 . . ?
C23 C24 H10 119.7 . . ?
C24 C25 C20 118.9(3) . . ?
C24 C25 H9 120.5 . . ?
C20 C25 H9 120.5 . . ?
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 C2 1.745(2) . ?
S1 C1 1.758(2) . ?
N1 C1 1.339(3) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N2 C9 1.392(3) . ?
N2 C21 1.396(3) . ?
N2 C8 1.433(3) . ?
N3 C1 1.302(3) . ?
N3 C13 1.382(3) . ?
C2 C3 1.378(3) . ?
C2 C13 1.406(3) . ?
C3 C4 1.391(3) . ?
C3 H15 0.9300 . ?
C4 C14 1.398(3) . ?
C4 C5 1.485(3) . ?
C5 C6 1.387(3) . ?
C5 C17 1.388(3) . ?
C6 C7 1.373(3) . ?
C6 H14 0.9300 . ?
C7 C8 1.381(3) . ?
C7 H13 0.9300 . ?
C8 C16 1.375(3) . ?
C9 C10 1.380(4) . ?
C9 C19 1.411(3) . ?
C10 C11 1.381(4) . ?
C10 H12 0.9300 . ?
C11 C12 1.396(4) . ?
C11 H11 0.9300 . ?
C12 C18 1.365(4) . ?
C12 H1 0.9300 . ?
C13 C15 1.393(3) . ?
C14 C15 1.379(3) . ?
C14 H3 0.9300 . ?
C15 H2 0.9300 . ?
C16 C17 1.379(3) . ?
C16 H4 0.9300 . ?
C17 H5 0.9300 . ?
C18 C19 1.394(4) . ?
C18 H6 0.9300 . ?
C19 C20 1.438(4) . ?
C20 C25 1.394(4) . ?
C20 C21 1.407(3) . ?
C21 C22 1.385(4) . ?
C22 C23 1.380(4) . ?
C22 H7 0.9300 . ?
C23 C24 1.384(4) . ?
C23 H8 0.9300 . ?
C24 C25 1.379(4) . ?
C24 H10 0.9300 . ?
C25 H9 0.9300 . ?
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
_geom_hbond_publ_flag
N1 H1A N3 0.86 2.07 2.900(3) 161.1 3 yes
N1 H1A N3 0.86 2.07 2.900(3) 161.1 3 yes
N1 H1A N3 0.86 2.07 2.900(3) 161.1 3 yes
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
C13 N3 C1 N1 179.9(2) . . . . ?
C13 N3 C1 S1 -0.2(2) . . . . ?
C2 S1 C1 N3 0.06(19) . . . . ?
C2 S1 C1 N1 179.9(2) . . . . ?
C1 S1 C2 C3 177.7(2) . . . . ?
C1 S1 C2 C13 0.11(17) . . . . ?
C13 C2 C3 C4 -0.3(3) . . . . ?
S1 C2 C3 C4 -177.64(18) . . . . ?
C2 C3 C4 C14 -1.2(3) . . . . ?
C2 C3 C4 C5 173.5(2) . . . . ?
C3 C4 C5 C6 -137.1(2) . . . . ?
C14 C4 C5 C6 37.5(3) . . . . ?
C3 C4 C5 C17 36.7(3) . . . . ?
C14 C4 C5 C17 -148.7(2) . . . . ?
C17 C5 C6 C7 -3.8(4) . . . . ?
C4 C5 C6 C7 170.2(2) . . . . ?
C5 C6 C7 C8 0.8(4) . . . . ?
C6 C7 C8 C16 3.2(4) . . . . ?
C6 C7 C8 N2 -172.6(2) . . . . ?
C9 N2 C8 C16 131.7(3) . . . . ?
C21 N2 C8 C16 -69.0(3) . . . . ?
C9 N2 C8 C7 -52.5(3) . . . . ?
C21 N2 C8 C7 106.8(3) . . . . ?
C21 N2 C9 C10 178.9(2) . . . . ?
C8 N2 C9 C10 -19.1(4) . . . . ?
C21 N2 C9 C19 1.1(2) . . . . ?
C8 N2 C9 C19 163.0(2) . . . . ?
N2 C9 C10 C11 -178.5(2) . . . . ?
C19 C9 C10 C11 -0.9(3) . . . . ?
C9 C10 C11 C12 -0.2(4) . . . . ?
C10 C11 C12 C18 1.4(4) . . . . ?
C1 N3 C13 C15 179.9(2) . . . . ?
C1 N3 C13 C2 0.3(3) . . . . ?
C3 C2 C13 N3 -178.1(2) . . . . ?
S1 C2 C13 N3 -0.3(2) . . . . ?
C3 C2 C13 C15 2.3(3) . . . . ?
S1 C2 C13 C15 -179.89(17) . . . . ?
C3 C4 C14 C15 0.7(3) . . . . ?
C5 C4 C14 C15 -173.9(2) . . . . ?
C4 C14 C15 C13 1.3(3) . . . . ?
N3 C13 C15 C14 177.7(2) . . . . ?
C2 C13 C15 C14 -2.7(3) . . . . ?
C7 C8 C16 C17 -4.0(4) . . . . ?
N2 C8 C16 C17 171.8(2) . . . . ?
C8 C16 C17 C5 0.9(4) . . . . ?
C6 C5 C17 C16 3.0(4) . . . . ?
C4 C5 C17 C16 -170.9(2) . . . . ?
C11 C12 C18 C19 -1.6(4) . . . . ?
C12 C18 C19 C9 0.5(3) . . . . ?
C12 C18 C19 C20 -180.0(2) . . . . ?
C10 C9 C19 C18 0.8(3) . . . . ?
N2 C9 C19 C18 178.8(2) . . . . ?
C10 C9 C19 C20 -178.9(2) . . . . ?
N2 C9 C19 C20 -0.9(2) . . . . ?
C18 C19 C20 C25 1.3(4) . . . . ?
C9 C19 C20 C25 -179.1(2) . . . . ?
C18 C19 C20 C21 -179.2(2) . . . . ?
C9 C19 C20 C21 0.3(2) . . . . ?
C9 N2 C21 C22 178.5(2) . . . . ?
C8 N2 C21 C22 16.1(4) . . . . ?
C9 N2 C21 C20 -0.9(2) . . . . ?
C8 N2 C21 C20 -163.25(19) . . . . ?
C25 C20 C21 C22 0.5(3) . . . . ?
C19 C20 C21 C22 -179.1(2) . . . . ?
C25 C20 C21 N2 179.9(2) . . . . ?
C19 C20 C21 N2 0.4(2) . . . . ?
N2 C21 C22 C23 -179.9(2) . . . . ?
C20 C21 C22 C23 -0.6(4) . . . . ?
C21 C22 C23 C24 -0.2(4) . . . . ?
C22 C23 C24 C25 1.1(4) . . . . ?
C23 C24 C25 C20 -1.2(4) . . . . ?
C21 C20 C25 C24 0.5(3) . . . . ?
C19 C20 C25 C24 179.8(2) . . . . ?
