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_7129728
_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         'C72 H67 Si'
_chemical_formula_sum            'C72 H67 Si'
_chemical_formula_weight         960.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-12-16
_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                90
_cell_angle_beta                 109.503(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.7578(7)
_cell_length_b                   16.3981(5)
_cell_length_c                   22.2474(8)
_cell_measurement_reflns_used    15863
_cell_measurement_temperature    120.15
_cell_measurement_theta_max      30.5400
_cell_measurement_theta_min      1.5710
_cell_volume                     5418.8(4)
_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 1.000
_diffrn_measured_fraction_theta_max 0.850
_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    -29.00  67.00   0.50    3.39    --   -7.01  57.00   0.00  192
  2  \w     -9.00  87.00   0.50    3.39    --   12.33  57.00 -60.00  192
  3  \w    -16.00  87.00   0.50    3.39    --   12.33  77.00-180.00  206
  4  \w     -9.00  87.00   0.50    3.39    --   12.33  57.00  60.00  192
  5  \w    -11.00  52.00   0.50    3.39    --   12.33 -99.00 -90.00  126
  6  \w     21.00  69.00   0.50    3.39    --   12.33-131.00-169.00   96
  7  \w    -11.00  14.00   0.50    3.39    --   12.33 -99.00 120.00   50
  8  \w     24.00  74.00   0.50    3.39    --   12.33-138.00  14.00  100
;
_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      0.0309912000
_diffrn_orient_matrix_UB_12      0.0301379000
_diffrn_orient_matrix_UB_13      -0.0023997000
_diffrn_orient_matrix_UB_21      -0.0307940000
_diffrn_orient_matrix_UB_22      0.0310122000
_diffrn_orient_matrix_UB_23      0.0011430000
_diffrn_orient_matrix_UB_31      0.0192623000
_diffrn_orient_matrix_UB_32      0.0010774000
_diffrn_orient_matrix_UB_33      0.0337283000
_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  0.0915
_diffrn_reflns_av_unetI/netI     0.0789
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.850
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            89518
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.850
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.868
_diffrn_reflns_theta_min         1.576
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48114
_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            'metallic reddish violet'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.177
_exptl_crystal_description       prism
_exptl_crystal_F_000             2052
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     670
_refine_ls_number_reflns         14510
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.1269
_refine_ls_R_factor_gt           0.0644
_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^)+(0.0860P)^2^+0.9572P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1565
_refine_ls_wR_factor_ref         0.1832
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8404
_reflns_number_total             14510
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc00548d1.cif
_cod_data_source_block           xtn201215
_cod_database_code               7129728
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C91 H67'
_chemical_oxdiff_usercomment     TAntM_Diels-Alder
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.962
_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 Ternary CH refined with riding coordinates:
 C01T(H01), C01V(H2), C01X(H4)
2.b Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00J(H00J), C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q),
 C00R(H00R), C00S(H00S), C00T(H00T), C00W(H00W), C00X(H00X), C00Z(H00Z),
 C013(H013), C014(H014), C015(H015), C016(H016), C017(H017), C019(H019),
 C01A(H01A), C01B(H01B), C01C(H01C), C01D(H01D), C01G(H01G), C01H(H01H),
 C01I(H01I), C01J(H01J), C01K(H01K), C01L(H01L)
2.c Idealised Me refined as rotating group:
 C01M(H01E,H01F,H01M), C01N(H01N,H01O,H01P), C01O(H01Q,H01R,H01S), C01P(H01T,
 H01U,H01V), C01Q(H01W,H01X,H01Y), C01S(H01Z,H,HA), C01U(H1,HB,HC), C01W(H3,HD,
 HE), C01Y(H5,HF,HG), C01Z(H6,HH,HI), C020(H02A,H02B,H02C), C021(H02D,H02E,H02F)
;
_shelx_res_checksum              37154
_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 2.737
_oxdiff_exptl_absorpt_empirical_full_min 0.416