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#$Date: 2025-04-05 06:53:21 +0300 (Sat, 05 Apr 2025) $
#$Revision: 299048 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/35/7063592.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_7063592
loop_
_publ_author_name
'Short, Jonathan I.'
'Rushbridge, Elizabeth K.'
'Blundell, Toby J.'
'Ogar, Joseph O.'
'Yang, Songjie'
'Wallis, John D.'
'Martin, Lee'
_publ_section_title
;
 A series of enantiopure BEDT-TTF-acetamide derivatives with two
 stereogenic centres
;
_journal_issue                   3
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              910
_journal_page_last               920
_journal_paper_doi               10.1039/D4NJ03967J
_journal_volume                  49
_journal_year                    2025
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C16 H17 N O S5'
_chemical_formula_sum            'C16 H17 N O S5'
_chemical_formula_weight         399.60
_chemical_melting_point          487
_chemical_name_common            1S5S5T
_chemical_name_systematic
(1'S,5S)-N-(1'-(4''-methylphenyl)-ethyl)-2-thioxo-5,6-dihydro-[1,3]dithiolo[4,5-b][1,4]dithiin-5-yl-acetamide
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2024-05-28
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-09-07 deposited with the CCDC.	2024-12-11 downloaded from the CCDC.
;
_cell_angle_alpha                100.0290(10)
_cell_angle_beta                 99.597(2)
_cell_angle_gamma                100.468(2)
_cell_formula_units_Z            1
_cell_length_a                   4.71880(10)
_cell_length_b                   8.58740(10)
_cell_length_c                   11.6175(2)
_cell_measurement_reflns_used    18662
_cell_measurement_temperature    120
_cell_measurement_theta_max      78.0870
_cell_measurement_theta_min      3.9050
_cell_volume                     446.191(14)
_computing_cell_refinement       'CrysAlisPro 1.171.42.80a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.80a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.80a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.15
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            26019
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.909
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.959
_diffrn_reflns_theta_min         3.948
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.002
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.485
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.80a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_description       plate
_exptl_crystal_F_000             208
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM'
_exptl_crystal_size_max          0.172
_exptl_crystal_size_mid          0.106
_exptl_crystal_size_min          0.034
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
;
 Flack x determined using 1581 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.009(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3513
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0361
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0685P)²+0.1834P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0996
_refine_ls_wR_factor_ref         0.1006
_reflns_Friedel_coverage         0.912
_reflns_Friedel_fraction_full    0.969
_reflns_Friedel_fraction_max     0.867
_reflns_number_gt                3426
_reflns_number_total             3513
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4nj03967j2.cif
_cod_data_source_block           1S5S5T
_cod_depositor_comments
'Adding full bibliography for 7063591--7063600.cif.'
_cod_database_code               7063592
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C11(H11), C12(H12), C14(H14), C15(H15)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C16(H16A,H16B,H16C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'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
S1 S 1.2593(3) -0.16280(14) 0.80834(12) 0.0381(3) Uani 1 1 d . . . . .
S2 S 0.9430(2) 0.00501(12) 0.63983(10) 0.0293(3) Uani 1 1 d . . . . .
S3 S 1.0911(2) 0.14676(12) 0.89210(10) 0.0280(3) Uani 1 1 d . . . . .
S4 S 0.6734(3) 0.26706(13) 0.56543(10) 0.0333(3) Uani 1 1 d . . . . .
S5 S 0.8496(2) 0.43680(12) 0.87483(10) 0.0274(3) Uani 1 1 d . . . . .
O1 O 0.8275(8) 0.5833(5) 0.4396(4) 0.0398(9) Uani 1 1 d . . . . .
N1 N 0.3715(8) 0.6181(4) 0.3682(3) 0.0231(8) Uani 1 1 d . . . . .
H1 H 0.189004 0.606023 0.378788 0.024(13) Uiso 1 1 calc R . . . .
C1 C 1.1067(10) -0.0117(5) 0.7815(4) 0.0279(10) Uani 1 1 d . . . . .
C2 C 0.8397(11) 0.1885(5) 0.6826(4) 0.0271(10) Uani 1 1 d . . . . .
C3 C 0.9065(10) 0.2537(5) 0.8010(4) 0.0236(9) Uani 1 1 d . . . . .
C4 C 0.6767(10) 0.4737(5) 0.6401(4) 0.0240(9) Uani 1 1 d . . . . .
H4 H 0.878539 0.542879 0.652407 0.029 Uiso 1 1 calc R U . . .
C5 C 0.5845(10) 0.4782(6) 0.7591(4) 0.0293(10) Uani 1 1 d . . . . .
H5A H 0.397122 0.397899 0.747062 0.035 Uiso 1 1 calc R U . . .
H5B H 0.546141 0.586599 0.787034 0.035 Uiso 1 1 calc R U . . .
C6 C 0.4598(10) 0.5363(6) 0.5561(4) 0.0273(10) Uani 1 1 d . . . . .
H6A H 0.274914 0.452522 0.528154 0.033 Uiso 1 1 calc R U . . .
H6B H 0.412518 0.633579 0.601606 0.033 Uiso 1 1 calc R U . . .
C7 C 0.5717(10) 0.5794(5) 0.4480(4) 0.0253(9) Uani 1 1 d . . . . .
C8 C 0.4417(10) 0.6795(5) 0.2645(4) 0.0216(9) Uani 1 1 d . . . . .
H8 H 0.653179 0.737676 0.285612 0.026 Uiso 1 1 calc R U . . .
C9 C 0.4075(11) 0.5370(5) 0.1591(4) 0.0295(10) Uani 1 1 d . . . . .
H9A H 0.532007 0.463565 0.182958 0.044 Uiso 1 1 calc R U . . .
H9B H 0.467474 0.578264 0.091368 0.044 Uiso 1 1 calc R U . . .
H9C H 0.201341 0.478307 0.135896 0.044 Uiso 1 1 calc R U . . .
C10 C 0.2581(9) 0.8021(5) 0.2408(4) 0.0207(8) Uani 1 1 d . . . . .
C11 C 0.0968(10) 0.7993(5) 0.1277(4) 0.0236(9) Uani 1 1 d . . . . .
H11 H 0.101011 0.717145 0.062040 0.028 Uiso 1 1 calc R U . . .
C12 C -0.0691(10) 0.9137(5) 0.1092(4) 0.0257(9) Uani 1 1 d . . . . .
H12 H -0.176818 0.908170 0.031305 0.031 Uiso 1 1 calc R U . . .
C13 C -0.0807(10) 1.0365(5) 0.2025(4) 0.0266(10) Uani 1 1 d . . . . .
C14 C 0.0797(10) 1.0410(5) 0.3159(4) 0.0253(9) Uani 1 1 d . . . . .
H14 H 0.076396 1.124203 0.381015 0.030 Uiso 1 1 calc R U . . .
C15 C 0.2444(10) 0.9254(5) 0.3349(4) 0.0244(9) Uani 1 1 d . . . . .
H15 H 0.349451 0.930173 0.413129 0.029 Uiso 1 1 calc R U . . .
C16 C -0.2571(11) 1.1624(6) 0.1834(5) 0.0325(11) Uani 1 1 d . . . . .
H16A H -0.208068 1.208883 0.116043 0.049 Uiso 1 1 calc R U . . .
H16B H -0.210672 1.248215 0.255622 0.049 Uiso 1 1 calc R U . . .
H16C H -0.467546 1.112082 0.165948 0.049 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 0.0181 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'
O O 0.0492 0.0322 '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
C1 S2 C2 97.4(2) . . ?
C1 S3 C3 97.6(2) . . ?
C2 S4 C4 102.4(2) . . ?
C3 S5 C5 100.1(2) . . ?
C7 N1 H1 118.5 . . ?
C7 N1 C8 123.1(4) . . ?
C8 N1 H1 118.5 . . ?
S1 C1 S2 124.0(3) . . ?
S1 C1 S3 123.1(3) . . ?
S3 C1 S2 112.9(3) . . ?
S2 C2 S4 115.6(3) . . ?
C3 C2 S2 115.8(3) . . ?
C3 C2 S4 128.5(4) . . ?
S5 C3 S3 115.2(2) . . ?
C2 C3 S3 116.2(3) . . ?
C2 C3 S5 128.5(3) . . ?
S4 C4 H4 109.5 . . ?
C5 C4 S4 111.8(3) . . ?
C5 C4 H4 109.5 . . ?
C5 C4 C6 110.0(4) . . ?
C6 C4 S4 106.4(3) . . ?
C6 C4 H4 109.5 . . ?
S5 C5 H5A 108.6 . . ?
S5 C5 H5B 108.6 . . ?
C4 C5 S5 114.9(3) . . ?
C4 C5 H5A 108.6 . . ?
C4 C5 H5B 108.6 . . ?
H5A C5 H5B 107.5 . . ?
C4 C6 H6A 108.7 . . ?
C4 C6 H6B 108.7 . . ?
H6A C6 H6B 107.6 . . ?
C7 C6 C4 114.2(4) . . ?
C7 C6 H6A 108.7 . . ?
C7 C6 H6B 108.7 . . ?
O1 C7 N1 124.4(4) . . ?
O1 C7 C6 121.2(4) . . ?
N1 C7 C6 114.3(4) . . ?
N1 C8 H8 107.7 . . ?
N1 C8 C9 109.7(3) . . ?
N1 C8 C10 108.7(3) . . ?
C9 C8 H8 107.7 . . ?
C10 C8 H8 107.7 . . ?
C10 C8 C9 115.2(4) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C8 123.1(4) . . ?
C11 C10 C15 117.1(4) . . ?
C15 C10 C8 119.8(4) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 C10 121.5(4) . . ?
C12 C11 H11 119.3 . . ?
C11 C12 H12 119.4 . . ?
C11 C12 C13 121.2(4) . . ?
C13 C12 H12 119.4 . . ?
C12 C13 C14 117.9(4) . . ?
C12 C13 C16 121.7(4) . . ?
C14 C13 C16 120.3(5) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 C13 121.0(4) . . ?
C15 C14 H14 119.5 . . ?
C10 C15 H15 119.4 . . ?
C14 C15 C10 121.2(4) . . ?
C14 C15 H15 119.4 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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 1.645(5) . ?
S2 C1 1.739(5) . ?
S2 C2 1.748(5) . ?
S3 C1 1.723(5) . ?
S3 C3 1.745(4) . ?
S4 C2 1.754(5) . ?
S4 C4 1.831(5) . ?
S5 C3 1.744(5) . ?
S5 C5 1.807(5) . ?
O1 C7 1.222(6) . ?
N1 H1 0.8800 . ?
N1 C7 1.339(6) . ?
N1 C8 1.459(5) . ?
C2 C3 1.352(6) . ?
C4 H4 1.0000 . ?
C4 C5 1.514(6) . ?
C4 C6 1.529(6) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.518(6) . ?
C8 H8 1.0000 . ?
C8 C9 1.538(6) . ?
C8 C10 1.512(6) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.399(6) . ?
C10 C15 1.403(6) . ?
C11 H11 0.9500 . ?
C11 C12 1.386(6) . ?
C12 H12 0.9500 . ?
C12 C13 1.390(7) . ?
C13 C14 1.395(7) . ?
C13 C16 1.503(7) . ?
C14 H14 0.9500 . ?
C14 C15 1.392(6) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
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 H1 O1 0.88 1.94 2.808(5) 167.0 1_455 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
S2 C2 C3 S3 1.2(5) . . . . ?
S2 C2 C3 S5 177.5(3) . . . . ?
S4 C2 C3 S3 -176.5(3) . . . . ?
S4 C2 C3 S5 -0.2(7) . . . . ?
S4 C4 C5 S5 71.0(4) . . . . ?
S4 C4 C6 C7 -74.3(4) . . . . ?
N1 C8 C10 C11 -131.4(4) . . . . ?
N1 C8 C10 C15 48.5(5) . . . . ?
C1 S2 C2 S4 176.9(3) . . . . ?
C1 S2 C2 C3 -1.1(4) . . . . ?
C1 S3 C3 S5 -177.5(3) . . . . ?
C1 S3 C3 C2 -0.6(4) . . . . ?
C2 S2 C1 S1 -179.7(3) . . . . ?
C2 S2 C1 S3 0.6(3) . . . . ?
C2 S4 C4 C5 -43.8(4) . . . . ?
C2 S4 C4 C6 -163.9(3) . . . . ?
C3 S3 C1 S1 -179.8(3) . . . . ?
C3 S3 C1 S2 -0.2(3) . . . . ?
C3 S5 C5 C4 -52.9(4) . . . . ?
C4 S4 C2 S2 -167.6(3) . . . . ?
C4 S4 C2 C3 10.1(5) . . . . ?
C4 C6 C7 O1 -9.2(7) . . . . ?
C4 C6 C7 N1 173.4(4) . . . . ?
C5 S5 C3 S3 -166.7(3) . . . . ?
C5 S5 C3 C2 16.9(5) . . . . ?
C5 C4 C6 C7 164.5(4) . . . . ?
C6 C4 C5 S5 -171.1(3) . . . . ?
C7 N1 C8 C9 88.5(5) . . . . ?
C7 N1 C8 C10 -144.7(4) . . . . ?
C8 N1 C7 O1 -3.9(7) . . . . ?
C8 N1 C7 C6 173.4(4) . . . . ?
C8 C10 C11 C12 -180.0(4) . . . . ?
C8 C10 C15 C14 179.4(4) . . . . ?
C9 C8 C10 C11 -7.8(6) . . . . ?
C9 C8 C10 C15 172.0(4) . . . . ?
C10 C11 C12 C13 0.3(7) . . . . ?
C11 C10 C15 C14 -0.7(6) . . . . ?
C11 C12 C13 C14 -0.1(6) . . . . ?
C11 C12 C13 C16 179.3(4) . . . . ?
C12 C13 C14 C15 -0.4(6) . . . . ?
C13 C14 C15 C10 0.9(7) . . . . ?
C15 C10 C11 C12 0.2(6) . . . . ?
C16 C13 C14 C15 -179.9(4) . . . . ?
