#------------------------------------------------------------------------------
#$Date: 2024-02-04 13:35:58 +0200 (Sun, 04 Feb 2024) $
#$Revision: 289434 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/05/1570530.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_1570530
loop_
_publ_author_name
'Sun, Zhen'
'Xu, Wan'
'Qiu, Shuai'
'Ma, Zhiying'
'Li, Chunli'
'Zhang, Sheng'
'Wang, Hua'
_publ_section_title
;
 Thia[n]helicenes with long persistent phosphorescence.
;
_journal_issue                   3
_journal_name_full               'Chemical science'
_journal_page_first              1077
_journal_page_last               1087
_journal_paper_doi               10.1039/d3sc05480b
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C15 H14 S3 Si'
_chemical_formula_sum            'C15 H14 S3 Si'
_chemical_formula_weight         318.53
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2023-09-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-09-04 deposited with the CCDC.	2023-12-08 downloaded from the CCDC.
;
_cell_angle_alpha                94.58(2)
_cell_angle_beta                 99.657(16)
_cell_angle_gamma                114.95(2)
_cell_formula_units_Z            2
_cell_length_a                   7.373(4)
_cell_length_b                   8.088(5)
_cell_length_c                   14.380(8)
_cell_measurement_reflns_used    8808
_cell_measurement_temperature    150
_cell_measurement_theta_max      28.279
_cell_measurement_theta_min      2.824
_cell_volume                     755.5(8)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Helios multilayer optic'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0812
_diffrn_reflns_av_unetI/netI     0.0498
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17165
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        25.099
_diffrn_reflns_theta_max         25.099
_diffrn_reflns_theta_min         2.818
_diffrn_source_type              Microfocus
_exptl_absorpt_coefficient_mu    0.553
_exptl_absorpt_correction_T_max  0.2627
_exptl_absorpt_correction_T_min  0.1970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1495 before and 0.0928 after correction. The Ratio of minimum to maximum transmission is 0.7499. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.824
_refine_diff_density_min         -0.644
_refine_diff_density_rms         0.245
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.159
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2619
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.159
_refine_ls_R_factor_all          0.1095
_refine_ls_R_factor_gt           0.0999
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2545
_refine_ls_wR_factor_ref         0.2673
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2226
_reflns_number_total             2619
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc05480b2.cif
_cod_data_source_block           TB[4]H
_cod_depositor_comments
'Adding full bibliography for 1570529--1570532.cif.'
_cod_original_cell_volume        755.4(8)
_cod_database_code               1570530
_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_max   0.947
_shelx_estimated_absorpt_t_min   0.942
_diffrn_source_source            'Incoatc Ius 3.0 '
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C4(H4), C3(H3), C2(H2), C11(H11)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
S2 S 0.83661(19) 0.87684(17) 0.66535(9) 0.0240(4) Uani 1 1 d . . . . .
Si1 Si 0.6191(2) 0.25713(18) 0.89978(9) 0.0224(5) Uani 1 1 d . . . . .
S3 S 0.76199(19) 0.65495(17) 0.83970(9) 0.0243(4) Uani 1 1 d . . . . .
S1 S 0.82384(19) 0.78538(17) 0.44566(9) 0.0264(4) Uani 1 1 d . . . . .
C9 C 0.7428(7) 0.5238(7) 0.6655(3) 0.0210(11) Uani 1 1 d . . . . .
C5 C 0.7032(7) 0.2606(7) 0.4600(4) 0.0228(11) Uani 1 1 d . . . . .
H5 H 0.679948 0.184720 0.508095 0.027 Uiso 1 1 calc R . . . .
C4 C 0.6999(8) 0.1890(7) 0.3674(4) 0.0277(12) Uani 1 1 d . . . . .
H4 H 0.675784 0.063757 0.352995 0.033 Uiso 1 1 calc R . . . .
C10 C 0.7799(7) 0.6855(7) 0.7233(4) 0.0228(11) Uani 1 1 d . . . . .
C3 C 0.7316(8) 0.2988(7) 0.2958(4) 0.0275(12) Uani 1 1 d . . . . .
H3 H 0.727506 0.246499 0.233445 0.033 Uiso 1 1 calc R . . . .
C7 C 0.7591(7) 0.5554(7) 0.5689(4) 0.0236(11) Uani 1 1 d . . . . .
C6 C 0.7414(7) 0.4467(7) 0.4806(3) 0.0214(11) Uani 1 1 d . . . . .
C8 C 0.8042(7) 0.7358(7) 0.5598(4) 0.0241(11) Uani 1 1 d . . . . .
C2 C 0.7687(7) 0.4821(7) 0.3139(4) 0.0274(12) Uani 1 1 d . . . . .
H2 H 0.790693 0.556298 0.265080 0.033 Uiso 1 1 calc R . . . .
C15 C 0.3325(8) 0.1349(8) 0.8708(4) 0.0325(13) Uani 1 1 d . . . . .
H15A H 0.286543 0.037641 0.909979 0.049 Uiso 1 1 calc GR . . . .
H15B H 0.282524 0.079509 0.802939 0.049 Uiso 1 1 calc GR . . . .
H15C H 0.278058 0.223630 0.884459 0.049 Uiso 1 1 calc GR . . . .
C11 C 0.6981(7) 0.3741(7) 0.7182(4) 0.0236(11) Uani 1 1 d . . . . .
H11 H 0.669400 0.252884 0.690041 0.028 Uiso 1 1 calc R . . . .
C13 C 0.7121(9) 0.3894(8) 1.0248(4) 0.0316(13) Uani 1 1 d . . . . .
H13A H 0.680056 0.495368 1.026916 0.047 Uiso 1 1 calc GR . . . .
H13B H 0.860818 0.433472 1.044720 0.047 Uiso 1 1 calc GR . . . .
H13C H 0.643965 0.308509 1.068063 0.047 Uiso 1 1 calc GR . . . .
C14 C 0.7296(10) 0.0902(8) 0.8838(4) 0.0371(14) Uani 1 1 d . . . . .
H14A H 0.687856 0.000923 0.927515 0.056 Uiso 1 1 calc GR . . . .
H14B H 0.879675 0.157500 0.897947 0.056 Uiso 1 1 calc GR . . . .
H14C H 0.679356 0.024454 0.817645 0.056 Uiso 1 1 calc GR . . . .
C1 C 0.7729(7) 0.5547(7) 0.4057(4) 0.0226(11) Uani 1 1 d . . . . .
C12 C 0.6998(7) 0.4190(7) 0.8129(4) 0.0243(11) 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 0.0033 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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 '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
C8 S2 C10 88.9(2) . . ?
C15 Si1 C13 109.2(2) . . ?
C14 Si1 C15 110.9(3) . . ?
C14 Si1 C13 111.5(3) . . ?
C12 Si1 C15 107.9(2) . . ?
C12 Si1 C13 110.1(2) . . ?
C12 Si1 C14 107.1(3) . . ?
C10 S3 C12 91.9(2) . . ?
C8 S1 C1 90.0(2) . . ?
C10 C9 C7 110.6(5) . . ?
C10 C9 C11 111.0(5) . . ?
C11 C9 C7 138.4(5) . . ?
C4 C5 H5 120.6 . . ?
C4 C5 C6 118.8(5) . . ?
C6 C5 H5 120.6 . . ?
C5 C4 H4 119.5 . . ?
C3 C4 C5 121.1(5) . . ?
C3 C4 H4 119.5 . . ?
S3 C10 S2 133.1(3) . . ?
C9 C10 S2 114.5(4) . . ?
C9 C10 S3 112.4(4) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 C4 121.3(5) . . ?
C2 C3 H3 119.4 . . ?
C6 C7 C9 136.2(5) . . ?
C8 C7 C9 111.5(5) . . ?
C8 C7 C6 112.2(4) . . ?
C5 C6 C7 130.3(5) . . ?
C5 C6 C1 118.5(4) . . ?
C1 C6 C7 111.2(5) . . ?
S1 C8 S2 130.9(3) . . ?
C7 C8 S2 114.5(4) . . ?
C7 C8 S1 114.6(4) . . ?
C3 C2 H2 121.0 . . ?
C3 C2 C1 118.1(5) . . ?
C1 C2 H2 121.0 . . ?
Si1 C15 H15A 109.5 . . ?
Si1 C15 H15B 109.5 . . ?
Si1 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C9 C11 H11 122.6 . . ?
C12 C11 C9 114.9(4) . . ?
C12 C11 H11 122.6 . . ?
Si1 C13 H13A 109.5 . . ?
Si1 C13 H13B 109.5 . . ?
Si1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
Si1 C14 H14A 109.5 . . ?
Si1 C14 H14B 109.5 . . ?
Si1 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C6 C1 S1 112.0(4) . . ?
C2 C1 S1 125.8(4) . . ?
C2 C1 C6 122.2(5) . . ?
S3 C12 Si1 122.6(3) . . ?
C11 C12 Si1 127.3(4) . . ?
C11 C12 S3 109.8(4) . . ?
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
S2 C10 1.744(5) . ?
S2 C8 1.742(5) . ?
Si1 C15 1.869(6) . ?
Si1 C13 1.872(6) . ?
Si1 C14 1.866(6) . ?
Si1 C12 1.866(5) . ?
S3 C10 1.730(5) . ?
S3 C12 1.757(5) . ?
S1 C8 1.735(5) . ?
S1 C1 1.765(5) . ?
C9 C10 1.387(7) . ?
C9 C7 1.448(7) . ?
C9 C11 1.428(7) . ?
C5 H5 0.9500 . ?
C5 C4 1.402(7) . ?
C5 C6 1.405(7) . ?
C4 H4 0.9500 . ?
C4 C3 1.398(7) . ?
C3 H3 0.9500 . ?
C3 C2 1.383(8) . ?
C7 C6 1.440(7) . ?
C7 C8 1.376(7) . ?
C6 C1 1.428(7) . ?
C2 H2 0.9500 . ?
C2 C1 1.392(7) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C11 H11 0.9500 . ?
C11 C12 1.378(7) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 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
C9 C7 C6 C5 -1.5(9) . . . . ?
C9 C7 C6 C1 179.7(5) . . . . ?
C9 C7 C8 S2 1.8(5) . . . . ?
C9 C7 C8 S1 -179.3(3) . . . . ?
C9 C11 C12 Si1 172.1(4) . . . . ?
C9 C11 C12 S3 -0.8(6) . . . . ?
C5 C4 C3 C2 0.5(8) . . . . ?
C5 C6 C1 S1 -178.8(3) . . . . ?
C5 C6 C1 C2 -0.6(7) . . . . ?
C4 C5 C6 C7 -177.9(5) . . . . ?
C4 C5 C6 C1 0.8(7) . . . . ?
C4 C3 C2 C1 -0.3(8) . . . . ?
C10 S2 C8 S1 179.6(4) . . . . ?
C10 S2 C8 C7 -1.8(4) . . . . ?
C10 S3 C12 Si1 -172.5(3) . . . . ?
C10 S3 C12 C11 0.9(4) . . . . ?
C10 C9 C7 C6 178.8(5) . . . . ?
C10 C9 C7 C8 -0.8(6) . . . . ?
C10 C9 C11 C12 0.3(6) . . . . ?
C3 C2 C1 S1 178.2(4) . . . . ?
C3 C2 C1 C6 0.3(7) . . . . ?
C7 C9 C10 S2 -0.6(5) . . . . ?
C7 C9 C10 S3 179.9(3) . . . . ?
C7 C9 C11 C12 -179.1(5) . . . . ?
C7 C6 C1 S1 0.2(5) . . . . ?
C7 C6 C1 C2 178.3(4) . . . . ?
C6 C5 C4 C3 -0.7(7) . . . . ?
C6 C7 C8 S2 -177.9(3) . . . . ?
C6 C7 C8 S1 1.0(6) . . . . ?
C8 S2 C10 S3 -179.3(4) . . . . ?
C8 S2 C10 C9 1.3(4) . . . . ?
C8 S1 C1 C6 0.3(4) . . . . ?
C8 S1 C1 C2 -177.8(4) . . . . ?
C8 C7 C6 C5 178.0(5) . . . . ?
C8 C7 C6 C1 -0.7(6) . . . . ?
C15 Si1 C12 S3 96.9(3) . . . . ?
C15 Si1 C12 C11 -75.2(5) . . . . ?
C11 C9 C10 S2 179.9(3) . . . . ?
C11 C9 C10 S3 0.4(5) . . . . ?
C11 C9 C7 C6 -1.9(10) . . . . ?
C11 C9 C7 C8 178.6(5) . . . . ?
C13 Si1 C12 S3 -22.2(4) . . . . ?
C13 Si1 C12 C11 165.7(5) . . . . ?
C14 Si1 C12 S3 -143.6(3) . . . . ?
C14 Si1 C12 C11 44.3(5) . . . . ?
C1 S1 C8 S2 177.9(4) . . . . ?
C1 S1 C8 C7 -0.8(4) . . . . ?
C12 S3 C10 S2 179.9(4) . . . . ?
C12 S3 C10 C9 -0.7(4) . . . . ?
