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_1557761
_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         'C46 H51 N2, C24 B F20, C H2 Cl2'
_chemical_formula_sum            'C71 H53 B Cl2 F20 N2'
_chemical_formula_weight         1395.86
_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             2019-11-08
_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                94.923(3)
_cell_angle_beta                 102.959(3)
_cell_angle_gamma                114.918(4)
_cell_formula_units_Z            2
_cell_length_a                   13.2446(5)
_cell_length_b                   13.7731(5)
_cell_length_c                   20.2266(8)
_cell_measurement_reflns_used    8509
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      72.5760
_cell_measurement_theta_min      3.6280
_cell_volume                     3192.4(3)
_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 0.996
_diffrn_measured_fraction_theta_max 0.967
_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    -46.00 -10.00   1.00   10.00    --  -40.85 125.00   0.00   36
  2  \w   -118.00  -4.00   1.00   10.00    --  -40.85 -19.00 -90.00  114
  3  \w   -115.00 -22.00   1.00   10.00    --  -40.85 -38.00-150.00   93
  4  \w     28.00  92.00   1.00   10.00    --   40.85-125.00-180.00   64
  5  \w     28.00  53.00   1.00   10.00    --   40.85-125.00-150.00   25
  6  \w     51.00  93.00   1.00   10.00    --   40.85-128.00  49.00   42
  7  \w     34.00 133.00   1.00   40.00    --  105.15 -30.00-120.00   99
  8  \w     56.00  96.00   1.00   40.00    --  105.15-111.00 -60.00   40
  9  \w     98.00 125.00   1.00   40.00    --  105.15 -30.00  60.00   27
 10  \w     41.00 131.00   1.00   40.00    --  105.15 -30.00 -30.00   90
 11  \w    112.00 159.00   1.00   40.00    --  105.15  45.00 -90.00   47
 12  \w     31.00 104.00   1.00   40.00    --  105.15 -94.00 120.00   73
 13  \w     57.00 106.00   1.00   40.00    --  105.15-111.00  90.00   49
 14  \w    113.00 162.00   1.00   40.00    --  105.15  77.00 -60.00   49
 15  \w     83.00 109.00   1.00   40.00    --  105.15-111.00   0.00   26
 16  \w     61.00 109.00   1.00   40.00    --  105.15-111.00-120.00   48
 17  \w    115.00 147.00   1.00   40.00    --  105.15  77.00   0.00   32
 18  \w     40.00 121.00   1.00   40.00    --  105.15 -45.00 120.00   81
 19  \w    117.00 178.00   1.00   40.00    --  105.15  77.00  30.00   61
 20  \w     47.00  80.00   1.00   40.00    --  105.15 -30.00  60.00   33
 21  \w     48.00 119.00   1.00   40.00    --  105.15 -77.00 -60.00   71
;
_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      0.1245148000
_diffrn_orient_matrix_UB_12      0.0842402000
_diffrn_orient_matrix_UB_13      0.0047002000
_diffrn_orient_matrix_UB_21      0.0335407000
_diffrn_orient_matrix_UB_22      0.0152984000
_diffrn_orient_matrix_UB_23      0.0795546000
_diffrn_orient_matrix_UB_31      0.0362007000
_diffrn_orient_matrix_UB_32      -0.0924190000
_diffrn_orient_matrix_UB_33      -0.0047485000
_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  0.0282
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            22810
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.742
_diffrn_reflns_theta_min         3.615
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.832
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.672
_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 intense yellow'
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_description       plate
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.311
_exptl_crystal_size_mid          0.132
_exptl_crystal_size_min          0.052
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.494
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     873
_refine_ls_number_reflns         12281
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0433
_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^)+(0.0578P)^2^+1.0365P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1097
_refine_ls_wR_factor_ref         0.1185
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10158
_reflns_number_total             12281
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc01278e2.cif
_cod_data_source_block           dzw-112
_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        3192.5(2)
_cod_database_code               1557761
_shelx_shelxl_version_number     2018/3
_audit_contact_author            'Farzaneh Fadaei Tirani'
_chemical_oxdiff_formula         'C71 H54 B Cl2 F20 N2'
_shelx_estimated_absorpt_t_max   0.911
_shelx_estimated_absorpt_t_min   0.600
_reflns_odcompleteness_completeness 99.65
_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.a Ternary CH refined with riding coordinates:
 C4(H4), C29(H29), C32(H32), C41(H41), C44(H44)
2.b Secondary CH2 refined with riding coordinates:
 C71(H71A,H71B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C25(H25),
  C26(H26), C27(H27), C37(H37), C38(H38), C39(H39)
2.d Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C33(H33A,H33B,H33C), C34(H34A,H34B,
 H34C), C42(H42A,H42B,H42C), C43(H43A,H43B,H43C), C45(H45A,H45B,H45C), C46(H46A,
 H46B,H46C)
;
_shelx_res_checksum              94361
_olex2_date_sample_data_collection 2019-11-07
_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 1.844
_oxdiff_exptl_absorpt_empirical_full_min 0.696