DMF as an amine source: iron-catalyzed cyclization of 2<i>H</i>-azirines to imidazoles.
Zhao, Mi-Na; Yang, Zi-Mo; Li, Lian-Qing; Chemical communications (Cambridge, England) 60 (2024) 1904–1907; doi:10.1039/d3cc06147g

data_7132644
_publ_section_title
;
 DMF as an amine source: iron-catalyzed cyclization of 2<i>H</i>-azirines
 to imidazoles.
;
_journal_issue                   14
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1904
_journal_page_last               1907
_journal_paper_doi               10.1039/d3cc06147g
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C17 H16 N2'
_chemical_formula_sum            'C17 H16 N2'
_chemical_formula_weight         248.32
_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             2021-07-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-12-13 deposited with the CCDC.	2024-01-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.604(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.0756(12)
_cell_length_b                   8.8912(9)
_cell_length_c                   12.8700(12)
_cell_measurement_reflns_used    7394
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.43
_cell_measurement_theta_min      2.79
_cell_volume                     1380.4(2)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0702
_diffrn_reflns_av_unetI/netI     0.0465
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            27146
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.639
_diffrn_reflns_theta_min         2.785
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5958
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0747 before and 0.0636 after correction.
The Ratio of minimum to maximum transmission is 0.7991.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_density_meas      1.195
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.228
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         3225
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.228
_refine_ls_R_factor_all          0.1407
_refine_ls_R_factor_gt           0.0926
_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^)+(0.0654P)^2^+1.2310P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2094
_refine_ls_wR_factor_ref         0.2366
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2106
_reflns_number_total             3225
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc06147g2.cif
_cod_data_source_block           sust_3092_0m
_cod_depositor_comments          'Adding full bibliography for 7132644.cif.'
_cod_database_code               7132644
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C14(H14), C13(H13), C5(H5), C17(H17), C1(H1), C2(H2),
 C4(H4), C3(H3)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              97044
_shelx_hkl_checksum              55405
_olex2_submission_special_instructions 'No special instructions were received'