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_1570848
_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         'C40 H57 N3, C6 H6'
_chemical_formula_sum            'C46 H63 N3'
_chemical_formula_weight         657.99
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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                90
_cell_angle_beta                 92.839(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.277(3)
_cell_length_b                   10.5458(12)
_cell_length_c                   18.401(2)
_cell_measurement_reflns_used    7176
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      64.92
_cell_measurement_theta_min      2.18
_cell_volume                     3930.0(8)
_computing_cell_refinement       'SAINT v8.40B (Bruker, 2019)'
_computing_data_collection       'APEX4 v2022.1-1 (Bruker, 2022)'
_computing_data_reduction        'SAINT v8.40B (Bruker, 2019)'
_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    'XT (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.00
_diffrn_detector                 'Bruker APEX II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.920
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'Rigaku MicroMax-007HF'
_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  0.1170
_diffrn_reflns_av_unetI/netI     0.0793
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.920
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            64029
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.454
_diffrn_reflns_theta_min         2.182
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_type              'Bruker TXS'
_diffrn_source_voltage           40.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.478
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.5718
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1158 before and 0.0755 after correction.
The Ratio of minimum to maximum transmission is 0.7598.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.112
_exptl_crystal_description       block
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     450
_refine_ls_number_reflns         7157
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0986
_refine_ls_R_factor_gt           0.0714
_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^)+4.9207P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1465
_refine_ls_wR_factor_ref         0.1601
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5203
_reflns_number_total             7157
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc04543a2.cif
_cod_data_source_block           2b
_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               1570848
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.898
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C16(H16), C25(H25), C28(H28), C13(H13), C33(H33), C35(H35), C40(H40)
1.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C3(H3A,H3B), C5(H5A,H5B), C4(H4A,H4B), C36(H36A,H36B), C32(H32A,
 H32B), C39(H39A,H39B), C38(H38A,H38B), C37(H37A,H37B), C34(H34A,H34B)
1.c Aromatic/amide H refined with riding coordinates:
 C23(H23), C21(H21), C9(H9), C22(H22), C11(H11), C10(H10), C018(H018),
 C019(H019), C01A(H01A), C01B(H01B), C01C(H01C), C01D(H01D)
1.d Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C18(H18A,H18B,H18C), C14(H14A,H14B,H14C), C26(H26A,H26B,
 H26C), C30(H30A,H30B,H30C), C15(H15A,H15B,H15C), C29(H29A,H29B,H29C), C17(H17A,
 H17B,H17C)
;
_shelx_res_checksum              78949
_shelx_hkl_checksum              97853
_olex2_submission_special_instructions 'No special instructions were received'