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_7158965
_publ_section_title
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 Catalytic divergent synthesis of imidazoles <i>via</i> reaction
 condition-dependent [3 + 2] cyclization of TosMIC.
;
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_paper_doi               10.1039/d2ob01747d
_journal_year                    2022
_chemical_formula_moiety         'C26 H24 N2 O4 S'
_chemical_formula_sum            'C26 H24 N2 O4 S'
_chemical_formula_weight         460.53
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-08-27
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
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2022-09-24 deposited with the CCDC.	2022-10-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.077(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4115(7)
_cell_length_b                   17.4920(18)
_cell_length_c                   13.8909(10)
_cell_measurement_reflns_used    3085
_cell_measurement_temperature    179.99(10)
_cell_measurement_theta_max      27.4260
_cell_measurement_theta_min      2.3250
_cell_volume                     2281.0(3)
_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      179.99(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 0.835
_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     -1.00  28.00   1.00    5.00    --  -11.35 -99.00 -90.00   29
  2  \w    -61.00  36.00   1.00    5.00    --   11.90 -37.00  30.00   97
  3  \w    -17.00  53.00   1.00    5.00    --   11.90 -19.00  60.00   70
;
_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      0.0320845000
_diffrn_orient_matrix_UB_12      -0.0224478000
_diffrn_orient_matrix_UB_13      -0.0350795000
_diffrn_orient_matrix_UB_21      -0.0349843000
_diffrn_orient_matrix_UB_22      -0.0329196000
_diffrn_orient_matrix_UB_23      0.0164444000
_diffrn_orient_matrix_UB_31      -0.0588177000
_diffrn_orient_matrix_UB_32      0.0073190000
_diffrn_orient_matrix_UB_33      -0.0334988000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_unetI/netI     0.0733
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.835
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11730
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.835
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.646
_diffrn_reflns_theta_min         2.329
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.178
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75602
_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    1.341
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         1.873
_refine_diff_density_min         -1.308
_refine_diff_density_rms         0.121
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.428
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         5383
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.428
_refine_ls_R_factor_all          0.1763
_refine_ls_R_factor_gt           0.1315
_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^)+(0.0838P)^2^+4.6786P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2928
_refine_ls_wR_factor_ref         0.3166
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3493
_reflns_number_total             5383
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01747d2.cif
_cod_data_source_block           220113-1
_cod_database_code               7158965
_shelx_shelxl_version_number     2018/3
_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 Ternary CH refined with riding coordinates:
 C00G(H00G)
2.b Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00E(H00E), C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K),
 C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O), C00R(H00R), C00S(H00S),
 C00T(H00T), C00U(H00U)
2.c Idealised Me refined as rotating group:
 C00V(H00B,H00C,H00D), C00W(H00F,H00P,H00Q), C00X(H00V,H00W,H00X)
;
_shelx_res_checksum              66475
_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 1.358
_oxdiff_exptl_absorpt_empirical_full_min 0.704