SET processes in Lewis acid–base reactions: the tritylation of N-heterocyclic carbenes
Dong, Zhaowen; Pezzato, Cristian; Sienkiewicz, Andrzej; Scopelliti, Rosario; Fadaei-Tirani, Farzaneh; Severin, Kay; Chemical Science 11 (2020) 7615–7618; doi:10.1039/D0SC01278E

data_1557762
_publ_section_title
;
 SET processes in Lewis acid--base reactions: the tritylation of
 N-heterocyclic carbenes
;
_journal_issue                   29
_journal_name_full               'Chemical Science'
_journal_page_first              7615
_journal_page_last               7618
_journal_paper_doi               10.1039/D0SC01278E
_journal_volume                  11
_journal_year                    2020
_chemical_formula_moiety         'C24 B F20, C11 H21 N2'
_chemical_formula_sum            'C35 H21 B F20 N2'
_chemical_formula_weight         860.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-01-29 deposited with the CCDC.	2020-04-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.4773(13)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.40488(13)
_cell_length_b                   18.0272(3)
_cell_length_c                   11.08430(15)
_cell_measurement_reflns_used    12020
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      76.4140
_cell_measurement_theta_min      4.8900
_cell_volume                     1678.90(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Mercury 4.2.0 (CCDC, 2019)'
_computing_publication_material  'CIFTab (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2665
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_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   -116.00 -20.00   1.00    1.00    --  -42.88 -56.00  93.00   96
  2  \w    -64.00 -13.00   1.00    1.00    --  -42.88 125.00 150.00   51
  3  \w    -85.00 -22.00   1.00    1.00    --  -42.88 -37.00 -90.00   63
  4  \w   -109.00 -45.00   1.00    1.00    --  -42.88 -37.00   0.00   64
  5  \w    -33.00  -7.00   1.00    1.00    --  -42.88 125.00-150.00   26
  6  \w    -84.00 -56.00   1.00    1.00    --  -42.88 125.00  60.00   28
  7  \w     27.00  93.00   1.00    1.00    --   42.88-125.00 -30.00   66
  8  \w     40.00  66.00   1.00    4.00    --  112.00-111.00  90.00   26
  9  \w     64.00 140.00   1.00    4.00    --  112.00 -30.00 -60.00   76
 10  \w     84.00 168.00   1.00    4.00    --  112.00  62.00 -14.01   84
 11  \w     59.00 109.00   1.00    4.00    --  112.00-111.00 -90.00   50
 12  \w    115.00 178.00   1.00    4.00    --  112.00 111.00 120.00   63
 13  \w     93.00 139.00   1.00    4.00    --  112.00  45.00  30.00   46
 14  \w     37.00 108.00   1.00    4.00    --  112.00-111.00-150.00   71
 15  \w    133.00 177.00   1.00    4.00    --  112.00  45.00 -90.00   44
 16  \w     99.00 126.00   1.00    4.00    --  112.00  45.00 -90.00   27
 17  \w    122.00 169.00   1.00    4.00    --  112.00  50.00 -30.82   47
 18  \w     43.00 104.00   1.00    4.00    --  112.00 -94.00 120.00   61
 19  \w    124.00 178.00   1.00    4.00    --  112.00  61.00 -60.00   54
 20  \w     83.00 109.00   1.00    4.00    --  112.00  61.00 -60.00   26
 21  \w    153.00 178.00   1.00    4.00    --  112.00  30.00-120.00   25
 22  \w     83.00 165.00   1.00    4.00    --  112.00  61.00   0.00   82
 23  \w     87.00 128.00   1.00    4.00    --  112.00  45.00 -60.00   41
 24  \w     43.00 103.00   1.00    4.00    --  112.00 -61.00-180.00   60
 25  \w    137.00 176.00   1.00    4.00    --  112.00  45.00 120.00   39
 26  \w     83.00 109.00   1.00    4.00    --  112.00  61.00 -30.00   26
 27  \w     50.00 128.00   1.00    4.00    --  112.00 -61.00 -30.00   78
 28  \w     89.00 114.00   1.00    4.00    --  112.00  45.00 120.00   25
 29  \w     88.00 175.00   1.00    4.00    --  112.00  61.00  30.00   87
 30  \w    136.00 172.00   1.00    4.00    --  112.00 111.00 -90.00   36
 31  \w     89.00 115.00   1.00    4.00    --  112.00  50.00 -30.82   26
 32  \w    145.00 170.00   1.00    4.00    --  112.00  63.00 -22.43   25
 33  \w     51.00  78.00   1.00    4.00    --  112.00-111.00 -60.00   27
 34  \w     86.00 113.00   1.00    4.00    --  112.00  45.00 -30.00   27
 35  \w     83.00 111.00   1.00    4.00    --  112.00  63.00 -22.43   28
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_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  0.0184
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            16823
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.459
_diffrn_reflns_theta_min         4.684
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.609
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.282
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
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            'clear pale colourless'
_exptl_crystal_density_diffrn    1.702
_exptl_crystal_description       irregular
_exptl_crystal_F_000             860
_exptl_crystal_size_max          0.743
_exptl_crystal_size_mid          0.543
_exptl_crystal_size_min          0.417
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 3258 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(2)
_refine_ls_extinction_coef       0.0063(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     530
_refine_ls_number_reflns         6954
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0280
_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^)+(0.0512P)^2^+0.3201P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0772
_refine_ls_wR_factor_ref         0.0774
_reflns_Friedel_coverage         0.920
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                6925
_reflns_number_total             6954
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc01278e2.cif
_cod_data_source_block           dzw120
_cod_depositor_comments
;Adding full bibliography for 1557761--1557764.cif.

 Adding full bibliography for 1557761--1557764.cif.
;
_cod_original_cell_volume        1678.89(4)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1557762
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.381
_shelx_estimated_absorpt_t_max   0.553
_shelx_res_checksum              68931