Brønsted acid-catalyzed regioselective ring opening of 2<i>H</i>-azirines by 2-mercaptopyridines and related heterocycles; one pot access to imidazo[1,2-<i>a</i>]pyridines and imidazo[2,1-<i>b</i>]thiazoles.
Biswas, Subrata; Roy, Arnab; Duari, Surajit; Maity, Srabani; Elsharif, Asma M.; Biswas, Srijit; Organic & biomolecular chemistry 22 (2024) 4697–4703; doi:10.1039/d4ob00410h

data_7159955
_publ_section_title
;
 Br&#xf8;nsted acid-catalyzed regioselective ring opening of
 2<i>H</i>-azirines by 2-mercaptopyridines and related heterocycles; one
 pot access to imidazo[1,2-<i>a</i>]pyridines and
 imidazo[2,1-<i>b</i>]thiazoles.
;
_journal_issue                   23
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4697
_journal_page_last               4703
_journal_paper_doi               10.1039/d4ob00410h
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C14 H11 Cl N2'
_chemical_formula_sum            'C14 H11 Cl N2'
_chemical_formula_weight         242.69
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-09-11
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-09-21 deposited with the CCDC.	2024-05-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.144(7)
_cell_length_b                   7.159(2)
_cell_length_c                   15.509(5)
_cell_measurement_reflns_used    9440
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      27.04
_cell_measurement_theta_min      2.33
_cell_volume                     2347.6(13)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.991
_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  0.0921
_diffrn_reflns_av_unetI/netI     0.0707
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            24620
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.154
_diffrn_reflns_theta_min         2.332
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.302
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.4219
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1645 before and 0.0976 after correction.
The Ratio of minimum to maximum transmission is 0.5659.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear reddish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_description       needle
_exptl_crystal_F_000             1008
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethylacetate, Hexane'
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 1469 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.27(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         5109
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0470
_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^)+(0.0667P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1148
_refine_ls_wR_factor_ref         0.1299
_reflns_Friedel_coverage         0.911
_reflns_Friedel_fraction_full    0.977
_reflns_Friedel_fraction_max     0.973
_reflns_number_gt                3916
_reflns_number_total             5109
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00410h2.cif
_cod_data_source_block           os
_cod_depositor_comments
;

2024-06-28
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel

 Adding full bibliography for 7159955.cif.
;
_cod_original_cell_volume        2347.4(13)
_cod_original_formula_moiety     '2(C14 H11 Cl N2)'
_cod_original_formula_sum        'C28 H22 Cl2 N4'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     485.39
_cod_database_code               7159955
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.956
_shelx_estimated_absorpt_t_min   0.840
_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:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C12(H12), C13(H13),
 C16(H16), C17(H17), C18(H18), C19(H19), C23(H23), C24(H24), C26(H26), C27(H27)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C28(H28A,H28B,H28C)
;
_shelx_res_checksum              54092
_olex2_submission_special_instructions 'No special instructions were received'