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_7129730
_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         'C91 H67'
_chemical_formula_sum            'C91 H67'
_chemical_formula_weight         1160.44
_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             2021-01-18
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.10.09 svn.r3662 for Rigaku Oxford Diffraction, GUI svn.r5959)
;
_audit_update_record
;
2021-11-22 deposited with the CCDC.	2022-02-17 downloaded from the CCDC.
;
_cell_angle_alpha                63.340(3)
_cell_angle_beta                 70.016(3)
_cell_angle_gamma                86.686(3)
_cell_formula_units_Z            2
_cell_length_a                   15.4442(6)
_cell_length_b                   16.8575(5)
_cell_length_c                   17.7961(4)
_cell_measurement_reflns_used    24848
_cell_measurement_temperature    120.15
_cell_measurement_theta_max      30.2210
_cell_measurement_theta_min      1.6000
_cell_volume                     3866.1(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.75a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.75a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.75a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      120.15
_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 0.823
_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    -12.00  91.00   0.50  125.10    --   12.33  28.00 -46.00  206
  2  \w     65.00  90.00   0.50  125.10    --   12.33  37.00-120.00   50
  3  \w     -5.00  50.00   0.50  125.10    --   12.33  37.00-120.00  110
  4  \w    -16.00  87.00   0.50  125.10    --   12.33  77.00 -30.00  206
  5  \w    -24.00  30.00   0.50  125.10    --   12.33 -28.00 151.00  108
  6  \w    -11.00  52.00   0.50  125.10    --   12.33 -99.00 120.00  126
  7  \w    -41.00  -5.00   0.50  125.10    --   -7.01 -57.00  30.00   72
  8  \w    -10.00  51.00   0.50  125.10    --   12.33 -99.00 -60.00  122
  9  \w    -10.00  51.00   0.50  125.10    --   12.33 -99.00-180.00  122
 10  \w    -36.00  35.00   0.50  125.10    --   12.33 -37.00-150.00  142
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0463784000
_diffrn_orient_matrix_UB_12      -0.0103612000
_diffrn_orient_matrix_UB_13      -0.0070283000
_diffrn_orient_matrix_UB_21      -0.0075385000
_diffrn_orient_matrix_UB_22      -0.0136168000
_diffrn_orient_matrix_UB_23      0.0458919000
_diffrn_orient_matrix_UB_31      -0.0145509000
_diffrn_orient_matrix_UB_32      -0.0441924000
_diffrn_orient_matrix_UB_33      0.0108856000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0709
_diffrn_reflns_av_unetI/netI     0.0646
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.823
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            70269
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.823
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.645
_diffrn_reflns_theta_min         1.581
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.056
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88336
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.75a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dark violet'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    0.997
_exptl_crystal_description       plate
_exptl_crystal_F_000             1226
_exptl_crystal_preparation       Recrystallization
_exptl_crystal_recrystallization_method 'From chloroform and pentane'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     826
_refine_ls_number_reflns         19675
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.981
_refine_ls_R_factor_all          0.0909
_refine_ls_R_factor_gt           0.0633
_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^)+(0.1177P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1711
_refine_ls_wR_factor_ref         0.1855
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12823
_reflns_number_total             19675
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc00548d1.cif
_cod_data_source_block           xdi210116
_cod_original_cell_volume        3866.1(2)
_cod_database_code               7129730
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C91 H67'
_chemical_oxdiff_usercomment     TantM-A_Diels-Alder
_shelx_estimated_absorpt_t_max   0.998
_shelx_estimated_absorpt_t_min   0.986
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C00D(H00D), C00M(H00M), C00N(H00N), C00P(H00P), C00S(H00S), C00T(H00T),
 C00X(H00X), C010(H010), C011(H011), C012(H012), C015(H015), C016(H016),
 C017(H017), C019(H019), C01A(H01A), C01B(H01B), C01D(H01D), C01E(H01E),
 C01F(H01F), C01H(H01H), C01I(H01I), C01J(H01J), C01K(H01K), C01L(H01L),
 C01M(H01M), C01N(H01N), C01O(H01O), C01R(H01R), C01S(H01S), C01T(H01T),
 C01U(H01U), C01V(H01V), C01X(H01X), C01Y(H01Y), C01Z(H01Z), C020(H020),
 C021(H021), C022(H022), C024(H024), C025(H025), C027(H027), C028(H028),
 C029(H029), C02B(H02G), C02C(H02H), C02D(H02I), C02E(H02J), C02F(H02K),
 C02G(H02L)
2.b Idealised Me refined as rotating group:
 C01W(H01C,H01G,H01P), C023(H02A,H02B,H02C), C02A(H02D,H02E,H02F), C02H(H02M,
 H02N,H02O), C02I(H02P,H02Q,H02R), C02J(H02S,H02T,H02U)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              63050
_shelx_fab_checksum              23577
_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 3.275
_oxdiff_exptl_absorpt_empirical_full_min 0.452