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#$Date: 2025-08-22 00:13:44 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301852 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/00/7060023.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_7060023
loop_
_publ_author_name
'Gese, A.'
'Akter, M.'
'Schnakenburg, G.'
'García Alcaraz, A.'
'Espinosa Ferao, A.'
'Streubel, R.'
_publ_section_title
;
 P-Functionalized tetrathiafulvalenes from 1,3-dithiole-2-thiones?
;
_journal_issue                   39
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              17122
_journal_page_last               17128
_journal_paper_doi               10.1039/D0NJ02984J
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety         'C15 H11 O P S3'
_chemical_formula_sum            'C15 H11 O P S3'
_chemical_formula_weight         334.39
_chemical_name_systematic        AG-174-8
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2017-09-22
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2020-05-04 deposited with the CCDC.	2020-09-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 118.641(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9993(5)
_cell_length_b                   21.0026(9)
_cell_length_c                   9.2456(5)
_cell_measurement_reflns_used    6367
_cell_measurement_temperature    123
_cell_measurement_theta_max      29.54
_cell_measurement_theta_min      2.69
_cell_volume                     1533.68(15)
_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    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      123
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS-2T'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_collimation    '0.5 mm diameter, monocapillary'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7351
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_min         2.691
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_current           40
_diffrn_source_power             2.00
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.578
_exptl_absorpt_correction_T_max  0.9306
_exptl_absorpt_correction_T_min  0.8079
_exptl_absorpt_correction_type   integration
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.940
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3619
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.941
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0267
_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)+(0.0420P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0656
_refine_ls_wR_factor_ref         0.0677
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2861
_reflns_number_total             3619
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0nj02984j2.cif
_cod_data_source_block           5364
_cod_depositor_comments
'Adding full bibliography for 7060022--7060023.cif.'
_cod_original_cell_volume        1533.67(15)
_cod_database_code               7060023
_shelxl_version_number           2013-2
_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   0.893
_shelx_estimated_absorpt_t_min   0.846
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid bond restraints
 S3, C3
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
S1 S 0.67242(4) 0.55482(2) 0.86592(4) 0.02566(9) Uani 1 1 d . . . . .
S2 S 0.61875(5) 0.60905(2) 1.12313(5) 0.03521(11) Uani 1 1 d . . . . .
S3 S 0.76716(5) 0.47871(2) 1.16887(5) 0.03829(12) Uani 1 1 d . U . . .
P P 0.54727(4) 0.67659(2) 0.65032(4) 0.01899(9) Uani 1 1 d . . . . .
O O 0.48801(13) 0.74146(5) 0.66045(14) 0.0281(2) Uani 1 1 d . . . . .
C1 C 0.58580(16) 0.63082(7) 0.83022(17) 0.0213(3) Uani 1 1 d . . . . .
C2 C 0.56068(19) 0.65522(8) 0.95062(19) 0.0279(3) Uani 1 1 d . . . . .
H2 H 0.5128 0.6963 0.9411 0.033 Uiso 1 1 calc R . . . .
C3 C 0.68964(16) 0.54398(8) 1.05929(18) 0.0276(3) Uani 1 1 d . U . . .
C4 C 0.39820(16) 0.63233(6) 0.47455(17) 0.0194(3) Uani 1 1 d . . . . .
C5 C 0.30368(17) 0.58248(7) 0.48852(19) 0.0256(3) Uani 1 1 d . . . . .
H5 H 0.3265 0.5675 0.5941 0.031 Uiso 1 1 calc R . . . .
C6 C 0.17582(18) 0.55490(8) 0.3467(2) 0.0322(4) Uani 1 1 d . . . . .
H6 H 0.1114 0.5208 0.3555 0.039 Uiso 1 1 calc R . . . .
C7 C 0.14197(18) 0.57683(8) 0.1934(2) 0.0320(4) Uani 1 1 d . . . . .
H7 H 0.0535 0.5579 0.0973 0.038 Uiso 1 1 calc R . . . .
C8 C 0.23578(19) 0.62617(8) 0.17819(19) 0.0302(3) Uani 1 1 d . . . . .
H8 H 0.2125 0.6409 0.0722 0.036 Uiso 1 1 calc R . . . .
C9 C 0.36393(18) 0.65399(7) 0.31890(18) 0.0244(3) Uani 1 1 d . . . . .
H9 H 0.4285 0.6879 0.3092 0.029 Uiso 1 1 calc R . . . .
C10 C 0.74664(17) 0.67740(7) 0.64926(18) 0.0227(3) Uani 1 1 d . . . . .
C11 C 0.79037(18) 0.63332(8) 0.56454(19) 0.0280(3) Uani 1 1 d . . . . .
H11 H 0.7135 0.6003 0.5037 0.034 Uiso 1 1 calc R . . . .
C12 C 0.9463(2) 0.63722(10) 0.5683(2) 0.0389(4) Uani 1 1 d . . . . .
H12 H 0.9758 0.6072 0.5094 0.047 Uiso 1 1 calc R . . . .
C13 C 1.0588(2) 0.68522(10) 0.6585(2) 0.0459(5) Uani 1 1 d . . . . .
H13 H 1.1650 0.6882 0.6604 0.055 Uiso 1 1 calc R . . . .
C14 C 1.0175(2) 0.72839(10) 0.7451(3) 0.0465(5) Uani 1 1 d . . . . .
H14 H 1.0960 0.7607 0.8079 0.056 Uiso 1 1 calc R . . . .
C15 C 0.8613(2) 0.72504(8) 0.7413(2) 0.0351(4) Uani 1 1 d . . . . .
H15 H 0.8329 0.7550 0.8011 0.042 Uiso 1 1 calc R . . . .
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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
C3 S1 C1 97.28(8) . . ?
C2 S2 C3 97.30(8) . . ?
O P C1 110.32(7) . . ?
O P C4 113.47(6) . . ?
O P C10 112.43(7) . . ?
C4 P C1 106.79(6) . . ?
C4 P C10 108.35(7) . . ?
C10 P C1 104.98(6) . . ?
S1 C1 P 122.34(8) . . ?
C2 C1 S1 115.64(12) . . ?
C2 C1 P 121.85(12) . . ?
S2 C2 H2 121.4 . . ?
C1 C2 S2 117.24(13) . . ?
C1 C2 H2 121.4 . . ?
S2 C3 S1 112.54(9) . . ?
S3 C3 S1 123.06(10) . . ?
S3 C3 S2 124.40(10) . . ?
C5 C4 P 122.03(11) . . ?
C5 C4 C9 119.84(13) . . ?
C9 C4 P 117.72(11) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 C4 119.46(15) . . ?
C6 C5 H5 120.3 . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.37(15) . . ?
C7 C6 H6 119.8 . . ?
C6 C7 H7 119.7 . . ?
C6 C7 C8 120.60(14) . . ?
C8 C7 H7 119.7 . . ?
C7 C8 H8 120.2 . . ?
C7 C8 C9 119.53(15) . . ?
C9 C8 H8 120.2 . . ?
C4 C9 H9 119.9 . . ?
C8 C9 C4 120.20(14) . . ?
C8 C9 H9 119.9 . . ?
C11 C10 P 123.42(11) . . ?
C11 C10 C15 119.74(14) . . ?
C15 C10 P 116.83(12) . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C12 120.22(16) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 120.2 . . ?
C13 C12 C11 119.64(18) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.45(16) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.29(17) . . ?
C15 C14 H14 119.9 . . ?
C10 C15 H15 120.2 . . ?
C14 C15 C10 119.63(17) . . ?
C14 C15 H15 120.2 . . ?
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 1.7372(14) . ?
S1 C3 1.7339(16) . ?
S2 C2 1.7200(17) . ?
S2 C3 1.7275(18) . ?
S3 C3 1.6476(16) . ?
P O 1.4823(10) . ?
P C1 1.8050(15) . ?
P C4 1.7930(14) . ?
P C10 1.7990(14) . ?
C1 C2 1.339(2) . ?
C2 H2 0.9500 . ?
C4 C5 1.394(2) . ?
C4 C9 1.396(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.390(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.379(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.386(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.388(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.386(2) . ?
C10 C15 1.396(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.390(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.388(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.373(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.391(2) . ?
C15 H15 0.9500 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168349965
