Synthesis, properties and chemical modification of a persistent triisopropylsilylethynyl substituted tri(9-anthryl)methyl radical
Nishiuchi, Tomohiko; Ishii, Daisuke; Aibara, Seito; Sato, Hiroyasu; Kubo, Takashi; Chemical Communications  (2022) –; doi:10.1039/D2CC00548D

data_7129729
_publ_section_title
;
 Synthesis, properties and chemical modification of a persistent
 triisopropylsilylethynyl substituted tri(9-anthryl)methyl radical
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC00548D
_journal_year                    2022
_chemical_formula_moiety         'C132 H110 Si2'
_chemical_formula_sum            'C132 H110 Si2'
_chemical_formula_weight         1752.37
_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             2022-02-01
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-02-03 deposited with the CCDC.	2022-02-17 downloaded from the CCDC.
;
_cell_angle_alpha                70.519(7)
_cell_angle_beta                 69.212(7)
_cell_angle_gamma                83.824(6)
_cell_formula_units_Z            1
_cell_length_a                   12.1360(10)
_cell_length_b                   15.6410(11)
_cell_length_c                   16.9992(13)
_cell_measurement_reflns_used    3633
_cell_measurement_temperature    99(3)
_cell_measurement_theta_max      59.1670
_cell_measurement_theta_min      2.9020
_cell_volume                     2843.8(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.38a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.42.38a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.42.38a (Rigaku OD, 2021)'
_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      99(3)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.981
_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     26.00  69.00   0.50   20.00    --   65.22-125.00 -90.00   86
  2  \w     37.00  68.00   0.50   20.00    --   65.22-125.00 150.00   62
  3  \w     45.00  71.00   0.50   20.00    --   65.22-125.00  30.00   52
  4  \w    -76.00 -45.00   0.50   20.00    --  -65.40 -15.00 -30.00   62
  5  \w    -66.00 -40.00   0.50   20.00    --  -65.40   0.00-180.00   52
  6  \w   -108.00 -80.00   0.50   20.00    --  -65.40 -15.00 -30.00   56
  7  \w    -66.00 -41.00   0.50   20.00    --  -65.40 125.00 -60.00   50
  8  \w    -97.00 -30.00   0.50   20.00    --  -65.40   0.00-120.00  134
  9  \w   -107.00 -45.00   0.50   20.00    --  -65.40 -15.00  30.00  124
 10  \w   -107.00 -76.00   0.50   20.00    --  -65.40 -15.00 -60.00   62
 11  \w    -61.00 -36.00   0.50   20.00    --  -65.40 -15.00 -60.00   50
 12  \w     35.00  90.00   0.50   20.00    --   69.57-125.00-150.00  110
 13  \w     29.00  95.00   0.50   20.00    --   69.57-125.00   0.00  132
 14  \w     34.00  94.00   0.50   20.00    --   69.57-125.00  90.00  120
 15  \w     29.00  96.00   0.50   20.00    --   69.57-125.00 -60.00  134
 16  \w   -101.00 -48.00   0.50   20.00    --  -74.92 -15.00  90.00  106
 17  \w   -109.00 -46.00   0.50   20.00    --  -74.92   0.00 150.00  126
 18  \w   -101.00 -69.00   0.50   20.00    --  -74.92 125.00  90.00   64
 19  \w   -100.00 -58.00   0.50   20.00    --  -74.92 125.00   0.00   84
 20  \w    -73.00 -38.00   0.50   20.00    --  -78.67 125.00 -90.00   70
 21  \w   -115.00 -57.00   0.50   20.00    --  -78.67 -15.00 -60.00  116
 22  \w   -105.00 -79.00   0.50   20.00    --  -78.67 125.00 -90.00   52
 23  \w   -105.00 -70.00   0.50   20.00    --  -78.67 125.00-150.00   70
 24  \w    -69.00 -41.00   0.50   20.00    --  -78.67 125.00  60.00   56
 25  \w    -65.00 -37.00   0.50   20.00    --  -78.67 125.00-150.00   56
 26  \w    -78.00 -39.00   0.50   20.00    --  -78.67 125.00 150.00   78
 27  \w   -113.00 -43.00   0.50   20.00    --  -78.67   0.00-150.00  140
 28  \w   -109.00 -60.00   0.50   20.00    --  -78.67 -15.00 150.00   98
 29  \w   -103.00 -77.00   0.50   20.00    --  -79.61 119.00-108.86   52
 30  \w   -104.00 -55.00   0.50   20.00    --  -79.61 121.00 114.65   98
 31  \w    -74.00 -40.00   0.50   20.00    --  -79.61 125.00  81.67   68
 32  \w   -101.00 -42.00   0.50   20.00    --  -79.61 115.00  25.37  118
 33  \w   -104.00 -71.00   0.50   20.00    --  -79.61 121.00 169.63   66
 34  \w   -104.00 -38.00   0.50   20.00    --  -79.61 122.00-131.66  132
 35  \w   -102.00 -42.00   0.50   20.00    --  -79.61 117.00 -30.87  120
 36  \w   -106.00 -78.00   0.50   20.00    --  -79.61 125.00  81.67   56
 37  \w   -102.00 -42.00   0.50   20.00    --  -79.61 118.00  43.54  120
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix-Arc 150'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0683454000
_diffrn_orient_matrix_UB_12      -0.0522022000
_diffrn_orient_matrix_UB_13      -0.0647902000
_diffrn_orient_matrix_UB_21      0.1148127000
_diffrn_orient_matrix_UB_22      0.0137192000
_diffrn_orient_matrix_UB_23      0.0138320000
_diffrn_orient_matrix_UB_31      -0.0242126000
_diffrn_orient_matrix_UB_32      -0.0894629000
_diffrn_orient_matrix_UB_33      0.0778621000
_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  0.1380
_diffrn_reflns_av_unetI/netI     0.2075
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            35414
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.244
_diffrn_reflns_theta_min         2.932
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.629
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69844
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.38a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.023
_exptl_crystal_description       block
_exptl_crystal_F_000             930
_exptl_crystal_size_max          0.009
_exptl_crystal_size_mid          0.006
_exptl_crystal_size_min          0.006
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.925
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     607
_refine_ls_number_reflns         10230
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.925
_refine_ls_R_factor_all          0.2035
_refine_ls_R_factor_gt           0.0877
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1010P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1929
_refine_ls_wR_factor_ref         0.2489
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3899
_reflns_number_total             10230
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc00548d1.cif
_cod_data_source_block           nishiuchi_yellow
_cod_database_code               7129729
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O Si'
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.994
_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 Me refined with riding coordinates:
 C40(H40A,H40B,H40C), C63(H63A,H63B,H63C), C61(H61A,H61B,H61C), C38(H38A,H38B,
 H38C), C62(H62A,H62B,H62C), C39(H39A,H39B,H39C)
2.b Aromatic/amide H refined with riding coordinates:
 C30(H30), C8(H8), C22(H22), C13(H13), C43(H43), C28(H28), C20(H20), C27(H27),
 C46(H46), C12(H12), C21(H21), C5(H5), C23(H23), C14(H14), C29(H29), C50(H50),
 C45(H45), C6(H6), C59(H59), C53(H53), C15(H15), C7(H7), C36(H36), C44(H44),
 C57(H57), C34(H34), C52(H52), C51(H51)
2.c Idealised Me refined as rotating group:
 C66(H66A,H66B,H66C), C65(H65A,H65B,H65C), C64(H64A,H64B,H64C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              14328
_shelx_fab_checksum              42454
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.493
_oxdiff_exptl_absorpt_empirical_full_min 0.684