Crystallographic and spectroscopic studies on persistent triarylpropargyl cations.
Shimajiri, Takuya; Tsue, Taiga; Koakutsu, Shumpei; Ishigaki, Yusuke; Suzuki, Takanori; Chemical communications (Cambridge, England) 60 (2024) 7152–7155; doi:10.1039/d4cc01786b

data_7133114
_publ_section_title
;
 Crystallographic and spectroscopic studies on persistent triarylpropargyl
 cations.
;
_journal_issue                   56
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              7152
_journal_page_last               7155
_journal_paper_doi               10.1039/d4cc01786b
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C2 F6 N O4 S2, C24 H19 O'
_chemical_formula_sum            'C26 H19 F6 N O5 S2'
_chemical_formula_weight         603.54
_chemical_name_systematic        ts240209-tsue1-150K_auto
_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             2024-02-09
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-04-06 deposited with the CCDC.	2024-05-30 downloaded from the CCDC.
;
_cell_angle_alpha                117.8081(14)
_cell_angle_beta                 98.1608(11)
_cell_angle_gamma                104.9911(12)
_cell_formula_units_Z            4
_cell_length_a                   14.24260(18)
_cell_length_b                   14.5647(2)
_cell_length_c                   15.1706(2)
_cell_measurement_reflns_used    33431
_cell_measurement_temperature    150
_cell_measurement_theta_max      77.2310
_cell_measurement_theta_min      3.3890
_cell_volume                     2558.64(8)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     14.00 117.00   0.50    0.07    --   42.91  77.00 120.00  206
  2  \w     14.00 117.00   0.50    0.07    --   42.91  77.00  30.00  206
  3  \w     14.00 117.00   0.50    0.07    --   42.91  77.00 -60.00  206
  4  \w     14.00 117.00   0.50    0.07    --   42.91  77.00-150.00  206
  5  \w    -34.00  43.00   0.50    0.07    --   42.91 -38.00-180.00  154
  6  \w    -34.00  43.00   0.50    0.07    --   42.91 -38.00  60.00  154
  7  \w    -30.00  72.00   0.50    0.07    --   42.91 -77.00   0.00  204
  8  \w     39.00  71.00   0.50    0.16    --  112.36 -61.00 120.00   64
  9  \w     39.00  71.00   0.50    0.16    --  112.36 -61.00  90.00   64
 10  \w     39.00  71.00   0.50    0.16    --  112.36 -61.00   0.00   64
 11  \w     39.00 105.00   0.50    0.16    --  112.36 -77.00 -90.00  132
 12  \w     39.00 111.00   0.50    0.16    --  112.36-125.00 -60.00  144
 13  \w     38.00 108.00   0.50    0.16    --  112.36-111.00-146.00  140
 14  \w      3.00  89.00   0.50    0.07    --   42.91-111.00-146.00  172
 15  \w     39.00 111.00   0.50    0.16    --  112.36-125.00  90.00  144
 16  \w     39.00 111.00   0.50    0.16    --  112.36-125.00 120.00  144
 17  \w     90.00 178.00   0.50    0.16    --  112.36  61.00 -30.00  176
 18  \w     90.00 178.00   0.50    0.16    --  112.36  61.00  90.00  176
 19  \w     73.00 118.00   0.50    0.07    --   42.91 125.00  60.00   90
 20  \w     73.00 118.00   0.50    0.07    --   42.91 125.00  90.00   90
 21  \w     82.00 178.00   0.50    0.16    --  112.36 111.00 -53.00  192
 22  \w     90.00 178.00   0.50    0.16    --  112.36  61.00-150.00  176
 23  \w     73.00 118.00   0.50    0.07    --   42.91 125.00-150.00   90
 24  \w     73.00 118.00   0.50    0.07    --   42.91 125.00-120.00   90
 25  \w   -130.00 -32.00   0.50    0.16    -- -106.00 151.00  78.63  196
 26  \w   -126.00 -32.00   0.50    0.16    -- -106.00 144.00 173.61  188
 27  \w   -112.00 -32.00   0.50    0.16    -- -106.00 125.00  60.00  160
 28  \w   -112.00 -32.00   0.50    0.16    -- -106.00 125.00  30.00  160
 29  \w   -112.00 -32.00   0.50    0.16    -- -106.00 125.00 -30.00  160
 30  \w   -108.00 -30.00   0.50    0.16    -- -106.00 111.00 -53.00  156
 31  \w    -89.00  -2.00   0.50    0.07    --  -42.91 111.00 -53.00  174
 32  \w   -126.00 -32.00   0.50    0.16    -- -106.00 144.00-168.26  188
 33  \w   -105.00 -32.00   0.50    0.16    -- -106.00  77.00 -30.00  146
 34  \w   -105.00 -32.00   0.50    0.16    -- -106.00  77.00-150.00  146
 35  \w    -71.00 -32.00   0.50    0.16    -- -106.00  61.00 120.00   78
 36  \w   -177.00 -83.00   0.50    0.16    -- -106.00 -62.00 146.75  188
 37  \w   -177.00 -82.00   0.50    0.16    -- -106.00 -64.00 -63.70  190
 38  \w   -116.00 -14.00   0.50    0.07    --  -42.91 -77.00-150.00  204
 39  \w   -177.00 -78.00   0.50    0.16    -- -106.00 -75.00-109.86  198
 40  \w   -177.00 -79.00   0.50    0.16    -- -106.00 -81.00-119.92  196
 41  \w   -177.00 -81.00   0.50    0.16    -- -106.00-111.00-146.00  192
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0207933000
_diffrn_orient_matrix_UB_12      0.0798830000
_diffrn_orient_matrix_UB_13      0.1179846000
_diffrn_orient_matrix_UB_21      0.1134069000
_diffrn_orient_matrix_UB_22      0.0141886000
_diffrn_orient_matrix_UB_23      0.0200255000
_diffrn_orient_matrix_UB_31      0.0235281000
_diffrn_orient_matrix_UB_32      0.1000057000
_diffrn_orient_matrix_UB_33      -0.0153210000
_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  0.0409
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            49231
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.329
_diffrn_reflns_theta_min         3.376
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.653
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.328
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
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            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_description       block
_exptl_crystal_F_000             1232
_exptl_crystal_recrystallization_method
'obtained by recrystallization from CH2Cl2/Et2O'
_exptl_crystal_size_max          0.304
_exptl_crystal_size_mid          0.229
_exptl_crystal_size_min          0.174
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.00164(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     728
_refine_ls_number_reflns         10472
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0351
_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^)+(0.0589P)^2^+0.6592P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0991
_refine_ls_wR_factor_ref         0.1011
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9627
_reflns_number_total             10472
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc01786b2.cif
_cod_data_source_block           ts240209-tsue1-150k_auto
_cod_depositor_comments
'Adding full bibliography for 7133110--7133114.cif.'
_cod_original_cell_volume        2558.63(7)
_cod_database_code               7133114
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C26 H19 F6 N O5 S2'
_chemical_oxdiff_usercomment     '150 K'
_shelx_estimated_absorpt_t_max   0.661
_shelx_estimated_absorpt_t_min   0.503
_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:
 C32(H32), C49(H49), C40(H40), C8(H8), C34(H34), C6(H6), C14(H14), C23(H23),
 C17(H17), C46(H46), C48(H48), C16(H16), C43(H43), C15(H15), C41(H41), C47(H47),
  C22(H22), C42(H42), C20(H20), C21(H21)
2.b Idealised Me refined as rotating group:
 C36(H36A,H36B,H36C), C10(H10A,H10B,H10C), C38(H38A,H38B,H38C), C12(H12A,H12B,
 H12C), C37(H37A,H37B,H37C), C11(H11A,H11B,H11C)
;
_shelx_res_checksum              67127
_shelx_hkl_checksum              72437
_olex2_submission_original_sample_id ts240209-tsue1-150K_auto
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.872
_oxdiff_exptl_absorpt_empirical_full_min 0.668