Catalytic divergent synthesis of imidazoles <i>via</i> reaction condition-dependent [3 + 2] cyclization of TosMIC.
Zhao, Cheng; Gu, Man-Zhen; Chen, Yi-Yuan; Hu, Xiao-Wei; Xu, Yi-Bing; Lin, Xiao-Min; Liu, Xin-Ni; Chen, Long; Chen, Guo-Shu; Liu, Yun-Lin; Organic & biomolecular chemistry  (2022) –; doi:10.1039/d2ob01747d

data_7158966
_publ_section_title
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 Catalytic divergent synthesis of imidazoles <i>via</i> reaction
 condition-dependent [3 + 2] cyclization of TosMIC.
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_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_paper_doi               10.1039/d2ob01747d
_journal_year                    2022
_chemical_formula_moiety         'C18 H18 N2 O4 S2'
_chemical_formula_sum            'C18 H18 N2 O4 S2'
_chemical_formula_weight         390.46
_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             2022-08-31
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-09-24 deposited with the CCDC.	2022-10-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.037(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.9384(2)
_cell_length_b                   19.6239(8)
_cell_length_c                   15.6970(7)
_cell_measurement_reflns_used    2288
_cell_measurement_temperature    180.00(10)
_cell_measurement_theta_max      73.3880
_cell_measurement_theta_min      3.5940
_cell_volume                     1806.54(13)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      180.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -64.00 -18.00   1.00    1.50    --  -41.11  38.00   0.00   46
  2  \w   -115.00 -19.00   1.00    1.50    --  -41.11 -38.00  30.00   96
  3  \w      2.00  75.00   1.00    1.50    --   41.11 -99.00-180.00   73
  4  \w     66.00 110.00   1.00    2.00    --  107.58 -95.00-150.00   44
  5  \w     33.00 140.00   1.00    2.00    --  107.58 -77.00  60.00  107
  6  \w     82.00 110.00   1.00    2.00    --  107.58  45.00 120.00   28
  7  \w    151.00 176.00   1.00    2.00    --  107.58  45.00 120.00   25
  8  \w     95.00 149.00   1.00    2.00    --  107.58 125.00 150.00   54
  9  \w     94.00 170.00   1.00    2.00    --  107.58 125.00  60.00   76
 10  \w     78.00 173.00   1.00    2.00    --  107.58  61.00-150.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0668707000
_diffrn_orient_matrix_UB_12      -0.0754248000
_diffrn_orient_matrix_UB_13      0.0071362000
_diffrn_orient_matrix_UB_21      0.0643954000
_diffrn_orient_matrix_UB_22      -0.0139300000
_diffrn_orient_matrix_UB_23      -0.0897195000
_diffrn_orient_matrix_UB_31      0.2455583000
_diffrn_orient_matrix_UB_32      -0.0168624000
_diffrn_orient_matrix_UB_33      0.0422146000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_av_unetI/netI     0.0761
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6926
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.869
_diffrn_reflns_theta_min         3.634
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.908
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50190
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_description       needle
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.983
_refine_diff_density_min         -0.626
_refine_diff_density_rms         0.119
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3569
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0971
_refine_ls_R_factor_gt           0.0806
_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^)+(0.1049P)^2^+3.9905P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2106
_refine_ls_wR_factor_ref         0.2253
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2765
_reflns_number_total             3569
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01747d2.cif
_cod_data_source_block           220115-1
_cod_database_code               7158966
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
1.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C17(H17), C13(H13), C7(H7), C1(H1), C6(H6), C9(H9), C14(H14),
 C16(H16), C10(H10)
1.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C18(H18A,H18B,H18C)
;
_shelx_res_checksum              60913
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.079
_oxdiff_exptl_absorpt_empirical_full_min 0.352