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_1570844
_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         'C25 H41 N2 O'
_chemical_formula_sum            'C25 H41 N2 O'
_chemical_formula_weight         385.60
_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     iterative
_audit_block_doi                 10.5517/ccdc.csd.cc2ckb8k
_audit_creation_date             2022-07-19
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-11-22 deposited with the CCDC.	2024-01-19 downloaded from the CCDC.
;
_cell_angle_alpha                75.524(2)
_cell_angle_beta                 76.840(2)
_cell_angle_gamma                89.604(2)
_cell_formula_units_Z            4
_cell_length_a                   9.3426(7)
_cell_length_b                   13.6019(9)
_cell_length_c                   19.5752(13)
_cell_measurement_reflns_used    5717
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      21.72
_cell_measurement_theta_min      2.21
_cell_volume                     2342.0(3)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      273.15
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_av_unetI/netI     0.0907
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            16889
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.455
_diffrn_reflns_theta_min         2.119
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_T_max  0.743
_exptl_absorpt_correction_T_min  0.674
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 128767 reflections, Rint = 0.1724
 (20892 with I > 3sig(I), Rint = 0.0692)
;
_exptl_crystal_colour            'yellowish orange'
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.094
_exptl_crystal_description       block
_exptl_crystal_F_000             852
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.125
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     525
_refine_ls_number_reflns         8638
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.979
_refine_ls_R_factor_all          0.1265
_refine_ls_R_factor_gt           0.0626
_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^)+(0.0740P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1315
_refine_ls_wR_factor_ref         0.1566
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4908
_reflns_number_total             8638
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc04543a2.cif
_cod_data_source_block           full_a
_cod_depositor_comments
'Adding full bibliography for 1570844--1570850.cif.'
_cod_database_code               1570844
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.986
_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:
 C20(H20), C23(H23), C20'(H20'), C23'(H23')
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C14(H14A,H14B), C16(H16A,H16B), C4'(H4'A,H4'B), C14'(H14C,H14D),
 C16'(H16C,H16D)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C8'(H8'), C9'(H9'), C10'(H10')
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C17(H17A,H17B,
 H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C21(H21A,H21B,H21C), C22(H22A,
 H22B,H22C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C12'(H12D,H12E,H12F),
 C13'(H13D,H13E,H13F), C15'(H15D,H15E,H15F), C17'(H17D,H17E,H17F), C18'(H18D,
 H18E,H18F), C19'(H19D,H19E,H19F), C21'(H21D,H21E,H21F), C22'(H22D,H22E,H22F),
 C24'(H24D,H24E,H24F), C25'(H25D,H25E,H25F)
;
_shelx_res_checksum              58154
_shelx_hkl_checksum              18964
_olex2_submission_special_instructions 'No special instructions were received'