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_1570850
_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         'C24 H32 N2 Se'
_chemical_formula_sum            'C24 H32 N2 Se'
_chemical_formula_weight         427.494
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_Int_Tables_number      15
_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                 110.970(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.8071(9)
_cell_length_b                   13.3759(7)
_cell_length_c                   17.5615(8)
_cell_measurement_reflns_used    9946
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      26.41
_cell_measurement_theta_min      2.46
_cell_volume                     4344.5(4)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.9997
_diffrn_measured_fraction_theta_max 0.9982
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_Laue_measured_fraction_full 0.9997
_diffrn_reflns_Laue_measured_fraction_max 0.9982
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            44841
_diffrn_reflns_point_group_measured_fraction_full 0.9997
_diffrn_reflns_point_group_measured_fraction_max 0.9982
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.44
_diffrn_reflns_theta_min         1.88
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.739
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6253
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1540 before and 0.0564 after correction.
The Ratio of minimum to maximum transmission is 0.8389.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellowish
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1792.742
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.067
_exptl_crystal_size_min          0.055
_refine_diff_density_max         0.3434
_refine_diff_density_min         -0.2929
_refine_diff_density_rms         0.0553
_refine_ls_d_res_high            0.7981
_refine_ls_d_res_low             10.8385
_refine_ls_goodness_of_fit_ref   1.0371
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    47
_refine_ls_number_parameters     250
_refine_ls_number_reflns         4459
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0371
_refine_ls_R_factor_all          0.0254
_refine_ls_R_factor_gt           0.0218
_refine_ls_shift/su_max          -0.0005
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0225P)^2^+4.8153P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0539
_refine_ls_wR_factor_ref         0.0555
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              23
_reflns_limit_h_min              -24
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              21
_reflns_limit_l_min              0
_reflns_number_gt                4052
_reflns_number_total             4459
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d3sc04543a2.cif
_cod_data_source_block           4b
_cod_depositor_comments
'Adding full bibliography for 1570844--1570850.cif.'
_cod_database_code               1570850
_olex2_refinement_description
;
1.a Secondary CH2 refined with riding coordinates:
 C3(H3a,H3b), C2(H2a,H2b), C6(H6a,H6b), C5(H5a,H5b), C4(H4a,H4b)
1.b Aromatic/amide H refined with riding coordinates:
 C20(H20), C11(H11), C18(H18), C9(H9)
1.c Idealised Me refined as rotating group:
 C15(H15a,H15b,H15c), C24(H24a,H24b,H24c), C13(H13a,H13b,H13c), C23(H23a,H23b,
 H23c), C22(H22a,H22b,H22c), C14(H14a,H14b,H14c)
;
_olex2_submission_special_instructions 'No special instructions were received'