A sequential Ugi‒Smiles/transition-metal-free endo-dig Conia‒ene cyclization: the selective synthesis of saccharin substituted 2,5-dihydropyrroles
Seyrani, Hassan; Ramezanpour, Sorour; Vaezghaemi, Aref; Kobarfard, Farzad; New Journal of Chemistry 45 (2021) 15647–15654; doi:10.1039/D1NJ01159F

data_7060847
_publ_section_title
;
 A sequential Ugi--Smiles/transition-metal-free endo-dig Conia--ene
 cyclization: the selective synthesis of saccharin substituted
 2,5-dihydropyrroles
;
_journal_issue                   34
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              15647
_journal_page_last               15654
_journal_paper_doi               10.1039/D1NJ01159F
_journal_volume                  45
_journal_year                    2021
_chemical_formula_moiety         'C22 H22 N4 O5 S, 0.5(O), 0.5(H2 O)'
_chemical_formula_sum            'C22 H23 N4 O6 S'
_chemical_formula_weight         471.50
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2021-02-15
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6257)
;
_audit_update_record
;
2021-02-20 deposited with the CCDC.	2021-07-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.39
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   27.896(6)
_cell_length_b                   7.6894(15)
_cell_length_c                   22.958(5)
_cell_measurement_reflns_used    15170
_cell_measurement_temperature    290
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.7
_cell_volume                     4924.5(18)
_computing_cell_refinement       'Automar software package (3.3a, 2015)'
_computing_data_collection       'MAR345 dtb Program (1.24-4, 2013)'
_computing_data_reduction        'Automar software package (3.3a, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      290
_diffrn_detector                 'image-plate detector'
_diffrn_detector_area_resol_mean 0.81
_diffrn_detector_type            MAR345-dtb
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'one-circle diffractometer'
_diffrn_measurement_device_type  MAR345
_diffrn_measurement_method       'image-plate detector - phi oscillation'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            15163
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.748
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_target            Mo
_exptl_absorpt_coefficient_mu    0.174
_exptl_absorpt_correction_T_max  1.06716
_exptl_absorpt_correction_T_min  0.96891
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'R.H. Blessing, Acta Crystallogr., Sect A 1995, 51, 33-38'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1976
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     314
_refine_ls_number_reflns         4303
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.126
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0630
_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^)+(0.0801P)^2^+5.9839P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1716
_refine_ls_wR_factor_ref         0.1776
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3835
_reflns_number_total             4303
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1nj01159f2.cif
_cod_data_source_block           2_pl
_cod_depositor_comments          'Adding full bibliography for 7060847.cif.'
_cod_database_code               7060847
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.950
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Others
 Fixed Sof: O7(0.25) O6(0.5) H6D(0.5) H6E(0.5) O8(0.25)
3.a Free rotating group:
 O6(H6D,H6E)
3.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
3.c Aromatic/amide H refined with riding coordinates:
 N3(H3), C22(H22), C9(H9), C11(H11), C20(H20), C21(H21), C19(H19), C14(H14),
 C13(H13), C12(H12), C15(H15)
3.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C7(H7A,H7B,H7C)
;
_shelx_res_checksum              81485
_olex2_submission_special_instructions 'No special instructions were received'