Ambiphilicity of ring-expanded N-heterocyclic carbenes.
Vermersch, François; Wang, Victor T.; Abdellaoui, Mehdi; Jazzar, Rodolphe; Bertrand, Guy; Chemical science 15 (2024) 3707–3710; doi:10.1039/d3sc04543a

data_1570845
_publ_section_title
;
 Ambiphilicity of ring-expanded N-heterocyclic carbenes.
;
_journal_issue                   10
_journal_name_full               'Chemical science'
_journal_page_first              3707
_journal_page_last               3710
_journal_paper_doi               10.1039/d3sc04543a
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C38 H50 N2'
_chemical_formula_sum            'C38 H50 N2'
_chemical_formula_weight         534.80
_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
_audit_creation_date             2023-08-20
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.17 svn.r577a77a9 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-08-29 deposited with the CCDC.	2024-01-19 downloaded from the CCDC.
;
_cell_angle_alpha                69.2430(10)
_cell_angle_beta                 75.6740(10)
_cell_angle_gamma                87.5200(10)
_cell_formula_units_Z            2
_cell_length_a                   9.9626(2)
_cell_length_b                   12.7843(2)
_cell_length_c                   13.6552(2)
_cell_measurement_reflns_used    6076
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      68.17
_cell_measurement_theta_min      3.57
_cell_volume                     1573.84(5)
_computing_cell_refinement       'SAINT v8.38A (Bruker, 2017)'
_computing_data_collection       'APEX3 v2017.3-0 (Bruker, 2017)'
_computing_data_reduction        'SAINT v8.38A (Bruker, 2017)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker X8 APEX II'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17967
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.285
_diffrn_reflns_theta_min         3.573
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker Microstar FR-592'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.482
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1075 before and 0.0531 after correction. The Ratio of minimum to maximum transmission is 0.8085. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.129
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     370
_refine_ls_number_reflns         5563
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0397
_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^)+(0.0404P)^2^+0.5346P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.1023
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4681
_reflns_number_total             5563
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc04543a2.cif
_cod_data_source_block           1c
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' 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 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 1570844--1570850.cif.
;
_cod_database_code               1570845
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.976
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C24(H24), C36(H36), C1(H1), C33(H33), C21(H21)
1.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C11(H11A,H11B), C13(H13A,H13B), C12(H12A,H12B)
1.c Aromatic/amide H refined with riding coordinates:
 C17(H17), C19(H19), C29(H29), C9(H9), C31(H31), C5(H5), C18(H18), C30(H30),
 C8(H8), C6(H6)
1.d Idealised Me refined as rotating group:
 C38(H38A,H38B,H38C), C23(H23A,H23B,H23C), C35(H35A,H35B,H35C), C22(H22A,H22B,
 H22C), C37(H37A,H37B,H37C), C10(H10A,H10B,H10C), C25(H25A,H25B,H25C), C34(H34A,
 H34B,H34C), C26(H26A,H26B,H26C)
;
_shelx_res_checksum              22759
_shelx_hkl_checksum              89993
_olex2_submission_special_instructions 'No special instructions were received'