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_1557763
_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, C27 H37 N2, C H2 Cl2'
_chemical_formula_sum            'C52 H39 B Cl2 F20 N2'
_chemical_formula_weight         1153.56
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-11-11
_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                69.366(2)
_cell_angle_beta                 84.7909(18)
_cell_angle_gamma                78.9069(16)
_cell_formula_units_Z            2
_cell_length_a                   12.4784(2)
_cell_length_b                   12.6328(3)
_cell_length_c                   17.6483(5)
_cell_measurement_reflns_used    13414
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      72.5510
_cell_measurement_theta_min      3.7650
_cell_volume                     2554.12(11)
_computing_cell_refinement       'CrysAlisPro 1.171.40.62a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.62a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.62a (Rigaku OD, 2019)'
_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 0.970
_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   -102.00 -29.00   1.00    5.00    --  -41.04 -38.00-180.00   73
  2  \w   -111.00 -19.00   1.00    5.00    --  -41.04 -57.00 -30.00   92
  3  \w    -66.00  -2.00   1.00    5.00    --  -41.04  57.00 -30.00   64
  4  \w     23.00 114.00   1.00    5.00    --   41.04  38.00  90.00   91
  5  \w      7.00  82.00   1.00    5.00    --   41.04 -99.00 120.00   75
  6  \w    117.00 152.00   1.00   20.00    --  105.15  77.00 -60.00   35
  7  \w     27.00  98.00   1.00   20.00    --  105.15 -94.00 -60.00   71
  8  \w     70.00 142.00   1.00   20.00    --  105.15 178.00-180.00   72
  9  \w     85.00 177.00   1.00   20.00    --  105.15  30.00-150.00   92
 10  \w     68.00 108.00   1.00   20.00    --  105.15-112.00 -94.00   40
 11  \w     40.00 109.00   1.00   20.00    --  105.15-111.00 150.00   69
 12  \w     71.00 109.00   1.00   20.00    --  105.15-111.00  30.00   38
 13  \w     85.00 173.00   1.00   20.00    --  105.15  45.00 -90.00   88
 14  \w     50.00 130.00   1.00   20.00    --  105.15 -45.00 -60.00   80
 15  \w     35.00 130.00   1.00   20.00    --  105.15 -61.00 120.00   95
 16  \w     44.00 133.00   1.00   20.00    --  105.15 -30.00-120.00   89
;
_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      0.0338925000
_diffrn_orient_matrix_UB_12      -0.1220756000
_diffrn_orient_matrix_UB_13      0.0607858000
_diffrn_orient_matrix_UB_21      0.0024408000
_diffrn_orient_matrix_UB_22      -0.0496395000
_diffrn_orient_matrix_UB_23      -0.0684490000
_diffrn_orient_matrix_UB_31      0.1211743000
_diffrn_orient_matrix_UB_32      0.0114984000
_diffrn_orient_matrix_UB_33      -0.0180486000
_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  0.0106
_diffrn_reflns_av_unetI/netI     0.0135
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18050
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.740
_diffrn_reflns_theta_min         2.676
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.156
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.279
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.62a (Rigaku Oxford Diffraction, 2019)
 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            'clear colourless'
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_description       prism
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.486
_exptl_crystal_size_mid          0.426
_exptl_crystal_size_min          0.176
_refine_diff_density_max         0.930
_refine_diff_density_min         -0.949
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       0.0018(2)
_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   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     809
_refine_ls_number_reflns         9870
_refine_ls_number_restraints     439
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0520
_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^)+(0.0868P)^2^+1.9836P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1491
_refine_ls_wR_factor_ref         0.1510
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9345
_reflns_number_total             9870
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc01278e2.cif
_cod_data_source_block           dzw-113
_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_original_cell_volume        2554.11(11)
_cod_database_code               1557763
_shelx_shelxl_version_number     2018/3
_audit_contact_author            'Farzaneh Fadaei Tirani'
_chemical_oxdiff_formula         'C52 H39 B Cl2 F20 N2'
_shelx_estimated_absorpt_t_max   0.703
_shelx_estimated_absorpt_t_min   0.421
_reflns_odcompleteness_completeness 99.99
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Cl1A-C52A
 1.777 with sigma of 0.02
 Cl1B-C52B
 1.777 with sigma of 0.01
 Cl2-C52B = Cl2-C52A
 1.765 with sigma of 0.02
 Cl1B-Cl2 = Cl1A-Cl2
 2.916 with sigma of 0.04
 F1A-C29A \\sim F1B-C29B \\sim F2A-C30A \\sim F2B-C30B \\sim F3A-C31A \\sim
F3B-C31B \\sim F4A-C32A ~
 F4B-C32B \\sim F5A-C33A \\sim F5B-C33B
 with sigma of 0.02
3. Restrained planarity
 F5B, C31B, C29B, C33B, C28B, F1B, C30B, F2B, C32B, F3B, F4B
 with sigma of 0.1
 F5A, C31A, C29A, C33A, C28A, F1A, C30A, F2A, C32A, F3A, F4A
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
F2A \\sim C30A: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 2A
F1A \\sim F1B \\sim F2A \\sim F2B \\sim F3A \\sim F3B \\sim F4A \\sim F4B \\sim
F5A \\sim F5B \\sim C28A \\sim C28B \\sim C29A \\sim C29B \\sim C30A \\sim C30B
\\sim C31A \\sim C31B \\sim C32A \\sim C32B \\sim C33A \\sim C33B: within 2A
with sigma of 0.005 and sigma for terminal atoms of 0.01 within 2A
Cl1A \\sim Cl1B \\sim Cl2 \\sim C52A \\sim C52B: within 2A with sigma of 0.005
and sigma for terminal atoms of 0.01 within 2A
5. Others
 Sof(Cl1B)=Sof(C52B)=Sof(H52C)=Sof(H52D)=Sof(F1B)=Sof(F2B)=Sof(F3B)=Sof(F4B)=
 Sof(F5B)=Sof(C28B)=Sof(C29B)=Sof(C30B)=Sof(C31B)=Sof(C32B)=Sof(C33B)=1-FVAR(1)
 Sof(Cl1A)=Sof(C52A)=Sof(H52A)=Sof(H52B)=Sof(F1A)=Sof(F2A)=Sof(F3A)=Sof(F4A)=
 Sof(F5A)=Sof(C28A)=Sof(C29A)=Sof(C30A)=Sof(C31A)=Sof(C32A)=Sof(C33A)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C10(H10), C13(H13), C22(H22), C25(H25)
6.b Secondary CH2 refined with riding coordinates:
 C52A(H52A,H52B), C52B(H52C,H52D)
6.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C6(H6), C7(H7), C8(H8), C18(H18), C19(H19), C20(H20)
6.d Fitted hexagon refined as free rotating group:
 C28B(C29B,C30B,C31B,C32B,C33B)
6.e Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C26(H26A,H26B,H26C), C27(H27A,
 H27B,H27C)
;
_shelx_res_checksum              78945
_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 1.788
_oxdiff_exptl_absorpt_empirical_full_min 0.698