Transition-Metal-Free Three-Component Reaction: Additive Controlled Synthesis of Sulfonylated Imidazoles.
Liu, Wei; Zhang, Yu; He, Jiaming; Yu, Yue; Yuan, Jiajun; Ye, Xiaoyi; Zhang, Ziwu; Xue, Liang; Cao, Hua; The Journal of organic chemistry 84 (2019) 11348–11358; doi:10.1021/acs.joc.9b01818

data_4033821
_publ_section_title
;
 Transition-Metal-Free Three-Component Reaction: Additive Controlled
 Synthesis of Sulfonylated Imidazoles.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11348
_journal_page_last               11358
_journal_paper_doi               10.1021/acs.joc.9b01818
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C28 H21 Cl N2 O2 S'
_chemical_formula_sum            'C28 H21 Cl N2 O2 S'
_chemical_formula_weight         484.98
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-09-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                70.334(4)
_cell_angle_beta                 64.617(4)
_cell_angle_gamma                85.903(3)
_cell_formula_units_Z            2
_cell_length_a                   10.9009(4)
_cell_length_b                   10.9293(5)
_cell_length_c                   11.4670(6)
_cell_measurement_reflns_used    6470
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      28.9560
_cell_measurement_theta_min      2.3240
_cell_volume                     1158.02(11)
_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 (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_environment      N~2~
_diffrn_ambient_temperature      100.01(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 1.000
_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    -40.00  62.00   1.00    2.00    --  -11.59  57.00  90.00  102
  2  \w    -20.00  29.00   1.00    2.00    --  -11.59 -99.00  90.00   49
  3  \w    -85.00  17.00   1.00    2.00    --  -11.59 -57.00 -60.00  102
  4  \w    -13.00  86.00   1.00    2.00    --   11.74  37.00-150.00   99
  5  \w     34.00  99.00   1.00    2.00    --   11.74-178.00 -30.00   65
  6  \w     34.00  99.00   1.00    2.00    --   11.74-178.00  60.00   65
;
_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      0.0240100000
_diffrn_orient_matrix_UB_12      0.0433341000
_diffrn_orient_matrix_UB_13      -0.0686894000
_diffrn_orient_matrix_UB_21      0.0203915000
_diffrn_orient_matrix_UB_22      -0.0534161000
_diffrn_orient_matrix_UB_23      -0.0239981000
_diffrn_orient_matrix_UB_31      -0.0650614000
_diffrn_orient_matrix_UB_32      -0.0073272000
_diffrn_orient_matrix_UB_33      0.0019679000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12834
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.989
_diffrn_reflns_theta_max         24.989
_diffrn_reflns_theta_min         1.986
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.285
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87313
_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    1.391
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         4069
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0388
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0387P)^2^+0.8128P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0899
_refine_ls_wR_factor_ref         0.0950
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3558
_reflns_number_total             4069
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01818_si_002.cif
_cod_data_source_block           225s
_cod_original_cell_volume        1158.02(10)
_cod_database_code               4033821
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C16(H16)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C15(H15), C14(H14), C2(H2), C22(H22), C18(H18), C27(H27),
 C28(H28), C19(H19), C21(H21), C20(H20), C9(H9), C26(H26), C24(H24), C5(H5),
 C25(H25), C8(H8), C7(H7), C6(H6)
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.321
_oxdiff_exptl_absorpt_empirical_full_min 0.739