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_7133111
_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         'C24 H19 O, C F3 O3 S'
_chemical_formula_sum            'C25 H19 F3 O4 S'
_chemical_formula_weight         472.46
_chemical_name_systematic        ts240117-kakt1-150K_autored
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-01-24
_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                90
_cell_angle_beta                 99.989(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.3296(2)
_cell_length_b                   14.8403(4)
_cell_length_c                   19.7980(6)
_cell_measurement_reflns_used    13165
_cell_measurement_temperature    150
_cell_measurement_theta_max      76.7190
_cell_measurement_theta_min      2.1950
_cell_volume                     2120.85(11)
_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  (Sheldrick, 2015)'
_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 0.999
_diffrn_measured_fraction_theta_max 0.974
_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    -78.00  31.00   0.50    1.45    --  -42.91  90.00  54.00  218
  2  \w    -30.00  78.00   0.50    1.45    --   42.91 -90.00 -59.00  216
  3  \w   -177.00 -79.00   0.50    3.45    -- -106.00 -90.00 -59.00  196
  4  \w   -105.00 -32.00   0.50    3.45    -- -106.00  90.00  54.00  146
  5  \w     39.00 105.00   0.50    3.45    --  112.36 -90.00 -59.00  132
  6  \w    -26.00  38.00   0.50    1.45    --  -42.91  19.00  60.00  128
  7  \w    -43.00  34.00   0.50    1.45    --  -42.91  38.00   0.00  154
  8  \w     73.00 118.00   0.50    1.45    --   42.91 125.00   0.00   90
  9  \w     73.00 118.00   0.50    1.45    --   42.91 125.00 -90.00   90
 10  \w    -30.00  65.00   0.50    1.45    --   42.91 -57.00 120.00  190
 11  \w     73.00 118.00   0.50    1.45    --   42.91 125.00 150.00   90
 12  \w     73.00 118.00   0.50    1.45    --   42.91 125.00-180.00   90
 13  \w    -37.00  26.00   0.50    1.45    --   42.91 -19.00-150.00  126
 14  \w   -177.00 -84.00   0.50    3.45    -- -106.00 -45.00-180.00  186
 15  \w   -177.00 -77.00   0.50    3.45    -- -106.00 -77.00 -90.00  200
 16  \w   -177.00 -84.00   0.50    3.45    -- -106.00 -45.00-150.00  186
 17  \w    -71.00 -32.00   0.50    3.45    -- -106.00  61.00   0.00   78
 18  \w   -112.00 -32.00   0.50    3.45    -- -106.00 125.00-150.00  160
 19  \w   -112.00 -32.00   0.50    3.45    -- -106.00 125.00 -30.00  160
 20  \w   -105.00 -32.00   0.50    3.45    -- -106.00  77.00-120.00  146
 21  \w   -112.00 -32.00   0.50    3.45    -- -106.00 125.00  90.00  160
 22  \w   -177.00 -84.00   0.50    3.45    -- -106.00 -45.00 -60.00  186
 23  \w   -105.00 -32.00   0.50    3.45    -- -106.00  77.00 -30.00  146
 24  \w     90.00 178.00   0.50    3.45    --  112.36  61.00   0.00  176
 25  \w     89.00 178.00   0.50    3.45    --  112.36  30.00  30.00  178
 26  \w     90.00 178.00   0.50    3.45    --  112.36  45.00 120.00  176
 27  \w     39.00 105.00   0.50    3.45    --  112.36 -95.00  60.00  132
 28  \w     39.00  71.00   0.50    3.45    --  112.36 -61.00   0.00   64
 29  \w     39.00  71.00   0.50    3.45    --  112.36 -61.00 120.00   64
 30  \w     39.00  71.00   0.50    3.45    --  112.36 -61.00 150.00   64
 31  \w     90.00 178.00   0.50    3.45    --  112.36  61.00 150.00  176
 32  \w     39.00  71.00   0.50    3.45    --  112.36 -61.00  60.00   64
 33  \w     39.00  71.00   0.50    3.45    --  112.36 -61.00  90.00   64
 34  \w     79.00 178.00   0.50    3.45    --  112.36  90.00  54.00  198
 35  \w   -116.00 -14.00   0.50    1.45    --  -42.91 -77.00-120.00  204
 36  \w   -116.00 -14.00   0.50    1.45    --  -42.91 -77.00 -30.00  204
 37  \w   -116.00 -14.00   0.50    1.45    --  -42.91 -77.00   0.00  204
 38  \w   -116.00 -20.00   0.50    1.45    --  -42.91 -57.00 150.00  192
 39  \w   -116.00 -20.00   0.50    1.45    --  -42.91 -57.00  30.00  192
 40  \w   -116.00 -14.00   0.50    1.45    --  -42.91 -77.00 120.00  204
 41  \w     21.00 120.00   0.50    1.45    --   42.91  38.00 -90.00  198
 42  \w     14.00 117.00   0.50    1.45    --   42.91  77.00 -90.00  206
 43  \w     14.00 117.00   0.50    1.45    --   42.91  77.00 120.00  206
;
_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      0.0841334000
_diffrn_orient_matrix_UB_12      0.0944772000
_diffrn_orient_matrix_UB_13      -0.0044953000
_diffrn_orient_matrix_UB_21      0.0811126000
_diffrn_orient_matrix_UB_22      -0.0037756000
_diffrn_orient_matrix_UB_23      0.0771274000
_diffrn_orient_matrix_UB_31      0.1785756000
_diffrn_orient_matrix_UB_32      -0.0428021000
_diffrn_orient_matrix_UB_33      -0.0165850000
_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  0.0482
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            16796
_diffrn_reflns_point_group_measured_fraction_full 0.907
_diffrn_reflns_point_group_measured_fraction_max 0.869
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.271
_diffrn_reflns_theta_min         4.536
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.875
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.493
_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            'light red'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_description       plate
_exptl_crystal_F_000             976
_exptl_crystal_recrystallization_method
'obtained by recrystallization from MeCN/Et2O'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.611
_refine_diff_density_min         -0.640
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details
;
 Flack x determined using 1590 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.36(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         3924
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0624
_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^)+(0.1259P)^2^+2.1837P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1716
_refine_ls_wR_factor_ref         0.1729
_reflns_Friedel_coverage         0.780
_reflns_Friedel_fraction_full    0.815
_reflns_Friedel_fraction_max     0.763
_reflns_number_gt                3805
_reflns_number_total             3924
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc01786b2.cif
_cod_data_source_block           ts240117-kakt1-150k_autored
_cod_depositor_comments
'Adding full bibliography for 7133110--7133114.cif.'
_cod_database_code               7133111
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C25 H19 F3 O4 S'
_chemical_oxdiff_usercomment     150K
_shelx_estimated_absorpt_t_max   0.946
_shelx_estimated_absorpt_t_min   0.651
_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 Free rotating group:
 S2(O3,O4,O5,C6,F7,F8,F9)
2.b Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00E(H00E), C00J(H00J), C00M(H00M), C00N(H00N), C00P(H00P),
 C00R(H00R), C00S(H00S), C00U(H00U), C00W(H00W)
2.c Idealised Me refined as rotating group:
 C00Q(H00A,H00B,H00D), C00T(H00F,H00G,H00H), C00V(H00I,H00K,H00L)
;
_shelx_res_checksum              86889
_shelx_hkl_checksum              19571
_olex2_submission_original_sample_id ts240117-kakt1-150K_autored
_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 3.047
_oxdiff_exptl_absorpt_empirical_full_min 0.604