A series of enantiopure BEDT-TTF-acetamide derivatives with two stereogenic centres
Short, Jonathan I.; Rushbridge, Elizabeth K.; Blundell, Toby J.; Ogar, Joseph O.; Yang, Songjie; Wallis, John D.; Martin, Lee; New Journal of Chemistry 49 (2025) 910–920; doi:10.1039/D4NJ03967J

data_7063597
_publ_section_title
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 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         'C17 H17 N O3 S5'
_chemical_formula_sum            'C17 H17 N O3 S5'
_chemical_formula_weight         443.61
_chemical_melting_point          421
_chemical_name_common            1S5R8T
_chemical_name_systematic
'(1'S,5R)-N-(1'-(2'-phenyl-1'-methoxycarbonyl)ethyl)- 2-thioxo-5,6-dihydro-[1,3]dithiolo[4,5-b]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
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2024-09-07 deposited with the CCDC.	2024-12-11 downloaded from the CCDC.
;
_cell_angle_alpha                88.5400(10)
_cell_angle_beta                 83.4310(10)
_cell_angle_gamma                89.7430(10)
_cell_formula_units_Z            2
_cell_length_a                   5.10160(10)
_cell_length_b                   10.47510(10)
_cell_length_c                   18.4059(3)
_cell_measurement_reflns_used    29862
_cell_measurement_temperature    120
_cell_measurement_theta_max      79.2190
_cell_measurement_theta_min      2.4370
_cell_volume                     976.83(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.92a (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)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120
_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 0.927
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 100'
_diffrn_measurement_method       '\w 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  0.0566
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.927
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            41559
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.882
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.360
_diffrn_reflns_theta_min         2.417
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.625
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.159
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.92a (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            yellow
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_description       plate
_exptl_crystal_F_000             460
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: THF'
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.852
_refine_diff_density_min         -0.513
_refine_diff_density_rms         0.091
_refine_ls_abs_structure_details
;
 Flack x determined using 3291 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     473
_refine_ls_number_reflns         7506
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0534
_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/[\s^2^(Fo^2^)+(0.1199P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1453
_refine_ls_wR_factor_ref         0.1471
_reflns_Friedel_coverage         0.904
_reflns_Friedel_fraction_full    0.964
_reflns_Friedel_fraction_max     0.838
_reflns_number_gt                7235
_reflns_number_total             7506
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4nj03967j2.cif
_cod_data_source_block           1S5R8T
_cod_depositor_comments
'Adding full bibliography for 7063591--7063600.cif.'
_cod_database_code               7063597
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.896
_shelx_estimated_absorpt_t_min   0.196
_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:
 C4A(H4A), C8A(H8A), C5B(H5B), C8B(H8B)
2.b Secondary CH2 refined with riding coordinates:
 C5A(H5AA,H5AB), C6A(H6AA,H6AB), C11A(H11A,H11B), C4B(H4BA,H4BB), C6B(H6BA,
 H6BB), C11B(H11C,H11D)
2.c Aromatic/amide H refined with riding coordinates:
 N1A(H1A), C13A(H13A), C14A(H14A), C15A(H15A), C16A(H16A), C17A(H17A),
 N1B(H1B), C13B(H13B), C14B(H14B), C15B(H15B), C16B(H16B), C17B(H17B)
2.d Idealised Me refined as rotating group:
 C10A(H10A,H10B,H10C), C10B(H10D,H10E,H10F)
;
_shelx_res_checksum              11400
_olex2_submission_special_instructions 'No special instructions were received'