Rh(II)-Catalyzed Transannulation of 1,2,4-Oxadiazole Derivatives with 1-Sulfonyl-1,2,3-triazoles: Regioselective Synthesis of 5-Sulfonamidoimidazoles.
Strelnikova, Julia O.; Rostovskii, Nikolai V.; Starova, Galina L.; Khlebnikov, Alexander F.; Novikov, Mikhail S.; The Journal of organic chemistry 83 (2018) 11232–11244; doi:10.1021/acs.joc.8b01809

data_4035640
_publ_section_title
;
 Rh(II)-Catalyzed Transannulation of 1,2,4-Oxadiazole Derivatives with
 1-Sulfonyl-1,2,3-triazoles: Regioselective Synthesis of
 5-Sulfonamidoimidazoles.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11232
_journal_page_last               11244
_journal_paper_doi               10.1021/acs.joc.8b01809
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C24 H20 F N3 O4 S'
_chemical_formula_sum            'C24 H20 F N3 O4 S'
_chemical_formula_weight         465.49
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2018-05-08
_audit_creation_method
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Olex2 1.2
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
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_cell_angle_alpha                90
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_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.6211(5)
_cell_length_b                   10.3200(13)
_cell_length_c                   36.416(5)
_cell_measurement_reflns_used    908
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.9730
_cell_measurement_theta_min      3.4240
_cell_volume                     2112.5(4)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega  -52.00   29.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.2678   77.0000   30.0000 81

  2 omega   36.00   72.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -       23.2053   77.0000 -180.0000 36

  3 omega   49.00   89.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -       23.2053   77.0000 -150.0000 40
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_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1161494000
_diffrn_orient_matrix_UB_12      0.0248860000
_diffrn_orient_matrix_UB_13      0.0028597000
_diffrn_orient_matrix_UB_21      -0.0480318000
_diffrn_orient_matrix_UB_22      0.0630337000
_diffrn_orient_matrix_UB_23      0.0022472000
_diffrn_orient_matrix_UB_31      -0.0117497000
_diffrn_orient_matrix_UB_32      -0.0112681000
_diffrn_orient_matrix_UB_33      0.0191367000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0582
_diffrn_reflns_av_unetI/netI     0.1541
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            6488
_diffrn_reflns_point_group_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_min         2.984
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.26168
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_description       prizm
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_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.096
_refine_ls_abs_structure_details
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 Flack x determined using 719 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
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_refine_ls_abs_structure_Flack   -0.17(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4583
_refine_ls_number_restraints     0
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_refine_ls_R_factor_all          0.1252
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_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
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'w=1/[\s^2^(Fo^2^)+(0.0489P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_refine_ls_wR_factor_ref         0.1819
_reflns_Friedel_coverage         0.625
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_reflns_Friedel_fraction_max     0.874
_reflns_number_gt                3194
_reflns_number_total             4583
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01809_si_002.cif
_cod_data_source_block           103-6639-7815_yul1
_cod_database_code               4035640
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C24 H20 F N3 O4 S'
_reflns_odcompleteness_completeness 99.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.51
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H3(0.02) H10(0.023) H11(0.019) H13(0.02) H23(0.021) H14(0.025)
 H19(0.02) H20(0.024) H17(0.021) H8(0.024) H15(0.025) H22(0.023) H16(0.029)
 H7(0.021) H5A(0.042) H5B(0.042) H5C(0.042) H24A(0.046) H24B(0.046) H24C(0.046)
 Fixed X: H3(0.7335) H10(-0.5264) H11(-0.2269) H13(0.81) H23(0.2238)
 H14(0.9611) H19(0.8684) H20(0.9263) H17(0.2417) H8(-0.1935) H15(0.7554)
 H22(0.2863) H16(0.4026) H7(0.0958) H5A(-0.0087) H5B(0.02) H5C(-0.2292)
 H24A(0.8268) H24B(0.565) H24C(0.6228)
 Fixed Y: H3(0.7794) H10(0.546) H11(0.5133) H13(0.5418) H23(0.6061)
 H14(0.3714) H19(0.7548) H20(0.587) H17(0.3243) H8(0.8675) H15(0.1752)
 H22(0.4384) H16(0.153) H7(0.8374) H5A(1.0878) H5B(1.0971) H5C(1.0657)
 H24A(0.3619) H24B(0.3129) H24C(0.4162)
 Fixed Z: H3(0.3695) H10(0.2541) H11(0.2973) H13(0.3871) H23(0.4375)
 H14(0.4207) H19(0.4627) H20(0.5038) H17(0.3588) H8(0.2187) H15(0.4225)
 H22(0.4798) H16(0.3917) H7(0.2631) H5A(0.3095) H5B(0.3523) H5C(0.3351)
 H24A(0.5223) H24B(0.5171) H24C(0.5473)
;
_olex2_submission_special_instructions 'No special instructions were received'