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_1570847
_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         'C41 H59 N3, C6 H6'
_chemical_formula_sum            'C47 H65 N3'
_chemical_formula_weight         672.02
_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                 100.0250(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1396(4)
_cell_length_b                   20.3171(8)
_cell_length_c                   19.4251(7)
_cell_measurement_reflns_used    9928
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      25.58
_cell_measurement_theta_min      2.68
_cell_volume                     3940.6(3)
_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      273.15
_diffrn_detector                 'Bruker Photon III Area Detector'
_diffrn_detector_area_resol_mean 7.407
_diffrn_detector_type            'CPAD Area Detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0799
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            55840
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.724
_diffrn_reflns_theta_min         2.656
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_type              'Bruker TXS'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6212
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1687 before and 0.0652 after correction.
The Ratio of minimum to maximum transmission is 0.8335.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.133
_exptl_crystal_description       plate
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.024
_exptl_crystal_size_mid          0.023
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     480
_refine_ls_number_reflns         7503
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0441
_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^)+(0.0402P)^2^+1.4444P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0961
_refine_ls_wR_factor_ref         0.1063
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5678
_reflns_number_total             7503
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc04543a2.cif
_cod_data_source_block           2c
_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               1570847
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.999
_shelx_estimated_absorpt_t_min   0.998
_olex2_refinement_description
;
1. Restrained distances
 C17-C18A \\sim C17-C18
 with sigma of 0.02
 C17-C19A \\sim C17-C19
 with sigma of 0.02
2. Others
 Sof(H17A)=Sof(C18)=Sof(H18D)=Sof(H18E)=Sof(H18F)=Sof(C19)=Sof(H19D)=Sof(H19E)=
 Sof(H19F)=1-FVAR(1)
 Sof(H17)=Sof(C19A)=Sof(H19A)=Sof(H19B)=Sof(H19C)=Sof(C18A)=Sof(H18A)=
 Sof(H18B)=Sof(H18C)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C009(H009), C14(H14), C17(H17), C17(H17A), C26(H26), C31(H31), C33(H33),
 C36(H36)
3.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C30(H30A,
 H30B), C32(H32A,H32B), C34(H34A,H34B), C35(H35A,H35B), C37(H37A,H37B),
 C38(H38A,H38B)
3.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C22(H22), C23(H23), C24(H24), C1S(H1S),
 C2S(H2S), C3S(H3S), C4S(H4S), C5S(H5S), C6S(H6S)
3.d Idealised Me refined as rotating group:
 C00Y(H00A,H00B,H00C), C00S(H00D,H00E,H00F), C15(H15A,H15B,H15C), C16(H16A,
 H16B,H16C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C19A(H19A,H19B,H19C),
 C18A(H18A,H18B,H18C), C18(H18D,H18E,H18F), C19(H19D,H19E,H19F)
;
_shelx_res_checksum              98830
_shelx_hkl_checksum              47968
_olex2_submission_special_instructions 'No special instructions were received'