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_7063598
_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         'C24 H21 N O S8, C12 H2 F2 N4'
_chemical_formula_sum            'C36 H23 F2 N5 O S8'
_chemical_formula_weight         836.07
_chemical_name_common            (1R,5S)7.TCNQF2
_chemical_name_systematic
;
(1''R,5S)-N-(1''-(Naphth-1'''-yl)ethyl)-(BEDT-TTF)-acetamide. TCNQ-F4
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2024-09-05
_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                90
_cell_angle_beta                 90.1243(13)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.37100(8)
_cell_length_b                   8.61043(11)
_cell_length_c                   38.2183(5)
_cell_measurement_reflns_used    6883
_cell_measurement_temperature    120
_cell_measurement_theta_max      73.2680
_cell_measurement_theta_min      2.3940
_cell_volume                     1767.46(4)
_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)'
_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 0.943
_diffrn_measured_fraction_theta_max 0.860
_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  0.0248
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_Laue_measured_fraction_full 0.943
_diffrn_reflns_Laue_measured_fraction_max 0.860
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            11751
_diffrn_reflns_point_group_measured_fraction_full 0.815
_diffrn_reflns_point_group_measured_fraction_max 0.726
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.238
_diffrn_reflns_theta_min         3.469
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.112
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.590
_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            brown
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_description       plate
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.193
_exptl_crystal_size_mid          0.031
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 1741 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.012(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     509
_refine_ls_number_reflns         5531
_refine_ls_number_restraints     566
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0345
_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/[\s^2^(Fo^2^)+(0.0465P)^2^+0.8297P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0860
_refine_ls_wR_factor_ref         0.0875
_reflns_Friedel_coverage         0.581
_reflns_Friedel_fraction_full    0.667
_reflns_Friedel_fraction_max     0.572
_reflns_number_gt                5089
_reflns_number_total             5531
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4nj03967j2.cif
_cod_data_source_block           1R5S7tcnqf2
_cod_depositor_comments
'Adding full bibliography for 7063591--7063600.cif.'
_cod_database_code               7063598
_shelx_shelxl_version_number     2018/3
_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. Restrained distances
 C9A-C10A = C9B-C10B
 1.5 with sigma of 0.005
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C9B)=Sof(H9BA)=Sof(H9BB)=Sof(C10B)=Sof(H10C)=Sof(H10D)=1-FVAR(1)
 Sof(C9A)=Sof(H9AA)=Sof(H9AB)=Sof(C10A)=Sof(H10A)=Sof(H10B)=FVAR(1)
 Sof(F32)=Sof(F33)=Sof(H35)=Sof(H38)=1-FVAR(2)
 Sof(F31)=Sof(F34)=Sof(H36)=Sof(H39)=FVAR(2)
6.a Ternary CH refined with riding coordinates:
 C1(H1A), C13(H13)
6.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C9A(H9AA,H9AB), C10A(H10A,H10B), C9B(H9BA,H9BB), C10B(H10C,H10D),
  C11(H11A,H11B)
6.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C16(H16), C17(H17), C18(H18), C20(H20), C21(H21), C22(H22), C23(H23),
 C35(H35), C36(H36), C38(H38), C39(H39)
6.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_shelx_res_checksum              6367
_olex2_submission_special_instructions 'No special instructions were received'