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_1557764
_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         'B C24 F20, C40 H39 N2, 0.5[C7H8]'
_chemical_formula_sum            'C64 H39 B F20 N2'
_chemical_formula_weight         1226.78
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-01-17
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2019.10.11 svn.r3662 for OlexSys, GUI svn.r5962)
;
_audit_update_record
;
2020-01-28 deposited with the CCDC.	2020-04-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.0482(3)
_cell_length_b                   18.05071(19)
_cell_length_c                   34.8012(5)
_cell_measurement_reflns_used    41391
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      75.8550
_cell_measurement_theta_min      3.6070
_cell_volume                     11337.6(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2817
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_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    -76.00  10.00   1.00    2.35    --  -40.91 101.00 -97.00   86
  2  \w      9.00  36.00   1.00    2.35    --   40.91-101.00 158.00   27
  3  \w     81.00 107.00   1.00    9.37    --  112.00-101.00 158.00   26
  4  \w    119.00 145.00   1.00    9.37    --  112.00 101.00 -97.00   26
  5  \w    -58.00  32.00   1.00    2.35    --  -40.91  38.00 -90.00   90
  6  \w   -112.00 -14.00   1.00    2.35    --  -40.91 -57.00 120.00   98
  7  \w     42.00  96.00   1.00    2.35    --   40.91-125.00  90.00   54
  8  \w     62.00 115.00   1.00    2.35    --   40.91  38.00  60.00   53
  9  \w     -6.00  64.00   1.00    2.35    --   40.91 -38.00 -60.00   70
 10  \w    137.00 177.00   1.00    9.37    --  112.00  30.00  60.00   40
 11  \w     37.00  63.00   1.00    9.37    --  112.00-111.00 -60.00   26
 12  \w     87.00 126.00   1.00    9.37    --  112.00 -30.00 120.00   39
 13  \w     36.00 109.00   1.00    9.37    --  112.00-111.00-120.00   73
 14  \w     45.00  72.00   1.00    9.37    --  112.00 -61.00-150.00   27
 15  \w     37.00 109.00   1.00    9.37    --  112.00-111.00  30.00   72
 16  \w     85.00 123.00   1.00    9.37    --  112.00  30.00  60.00   38
 17  \w     37.00 109.00   1.00    9.37    --  112.00-111.00 -90.00   72
 18  \w     36.00  62.00   1.00    9.37    --  112.00-111.00 150.00   26
 19  \w     98.00 140.00   1.00    9.37    --  112.00 -30.00-150.00   42
 20  \w     46.00  72.00   1.00    9.37    --  112.00 -94.00-180.00   26
 21  \w    124.00 150.00   1.00    9.37    --  112.00  45.00-180.00   26
 22  \w    152.00 177.00   1.00    9.37    --  112.00 111.00 -60.00   25
 23  \w     65.00  91.00   1.00    9.37    --  112.00-111.00   0.00   26
 24  \w     75.00 140.00   1.00    9.37    --  112.00 -61.00-150.00   65
 25  \w     85.00 136.00   1.00    9.37    --  112.00  30.00 120.00   51
 26  \w    141.00 168.00   1.00    9.37    --  112.00  30.00 120.00   27
 27  \w     36.00 109.00   1.00    9.37    --  112.00-111.00  90.00   73
 28  \w     36.00 109.00   1.00    9.37    --  112.00-111.00 -30.00   73
 29  \w     24.00 160.00   1.00    9.37    --  112.00   0.00-120.00  136
 30  \w     54.00  97.00   1.00    9.37    --  112.00-111.00 120.00   43
 31  \w     77.00 109.00   1.00    9.37    --  112.00-111.00 150.00   32
 32  \w     71.00 103.00   1.00    9.37    --  112.00 178.00-180.00   32
 33  \w     70.00  98.00   1.00    9.37    --  112.00-111.00  60.00   28
 34  \w     40.00 121.00   1.00    9.37    --  112.00 -61.00  90.00   81
 35  \w     38.00  81.00   1.00    9.37    --  112.00 -30.00-150.00   43
 36  \w     58.00 135.00   1.00    9.37    --  112.00 -45.00 -60.00   77
 37  \w     82.00 113.00   1.00    9.37    --  112.00 178.00-120.00   31
 38  \w     48.00  93.00   1.00    9.37    --  112.00 -94.00 -90.00   45
 39  \w     39.00  77.00   1.00    9.37    --  112.00 -30.00 120.00   38
 40  \w     98.00 123.00   1.00    9.37    --  112.00 -61.00 -60.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0379433000
_diffrn_orient_matrix_UB_12      0.0324165000
_diffrn_orient_matrix_UB_13      0.0359227000
_diffrn_orient_matrix_UB_21      -0.0747451000
_diffrn_orient_matrix_UB_22      -0.0005879000
_diffrn_orient_matrix_UB_23      0.0213902000
_diffrn_orient_matrix_UB_31      0.0160676000
_diffrn_orient_matrix_UB_32      -0.0789229000
_diffrn_orient_matrix_UB_33      0.0145970000
_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  0.0448
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            127435
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.243
_diffrn_reflns_theta_min         3.528
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.138
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.375
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
 CrysAlisPro 1.171.40.69a (Rigaku Oxford Diffraction, 2020).
 Numerical absorption correction based on Gaussian integration over
 a multifaceted crystal model.
 Empirical absorption correction using spherical harmonics as
 implemented in SCALE3 ABSPACK scaling algorithm
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_description       prism
_exptl_crystal_F_000             4976
_exptl_crystal_size_max          0.585
_exptl_crystal_size_mid          0.297
_exptl_crystal_size_min          0.094
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     790
_refine_ls_number_reflns         11828
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0402
_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^)+(0.0568P)^2^+3.6391P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1068
_refine_ls_wR_factor_ref         0.1109
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10432
_reflns_number_total             11828
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc01278e2.cif
_cod_data_source_block           dzw-129a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Gaussian' was
changed to 'gaussian' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 1557761--1557764.cif.

 Adding full bibliography for 1557761--1557764.cif.
;
_cod_database_code               1557764
_shelx_shelxl_version_number     2018/3
_audit_contact_author            'Farzaneh Fadaei Tirani'
_chemical_oxdiff_formula         'C64 H39 B F20 N2'
_shelx_estimated_absorpt_t_max   0.901
_shelx_estimated_absorpt_t_min   0.556
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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:
 C2(H2), C3(H3), C6(H6), C8(H8), C15(H15), C17(H17), C24(H24), C25(H25),
 C26(H26), C27(H27), C28(H28), C30(H30), C31(H31), C32(H32), C33(H33), C34(H34),
  C36(H36), C37(H37), C38(H38), C39(H39), C40(H40)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C19(H19A,H19B,
 H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              61875
_shelx_fab_checksum              58364
_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
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 2.489
_oxdiff_exptl_absorpt_empirical_full_min 0.654