Iodine/DMSO-mediated one-pot access towards 1-aryl-2-(pyrazol-5-yl)ethane-1,2-diones via a domino reaction from functionalized pent-2-ene-1,5-diones
Ghatak, Trisha; Shah, Chandan; Althagafi, Ismail; Giri, Nand Gopal; Nath, Mahendra; Pratap, Ramendra; Organic & Biomolecular Chemistry 22 (2024) 1859–1870; doi:10.1039/D3OB01997G

data_7159790
_publ_section_title
;
 Iodine/DMSO-mediated one-pot access towards
 1-aryl-2-(pyrazol-5-yl)ethane-1,2-diones via a domino reaction from
 functionalized pent-2-ene-1,5-diones
;
_journal_issue                   9
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              1859
_journal_page_last               1870
_journal_paper_doi               10.1039/D3OB01997G
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C19 H16 N2 O4'
_chemical_formula_sum            'C19 H16 N2 O4'
_chemical_formula_weight         336.34
_chemical_name_systematic        none
_chemical_properties_physical    Moisture-sensitive
_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   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-07-02
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-07-03 deposited with the CCDC.	2024-01-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.107(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3993(5)
_cell_length_b                   19.2977(9)
_cell_length_c                   11.0438(6)
_cell_measurement_reflns_used    7962
_cell_measurement_temperature    298
_cell_measurement_theta_max      29.7950
_cell_measurement_theta_min      3.3050
_cell_volume                     1710.86(17)
_computing_cell_refinement       'CrysAlisPro 1.171.42.69a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.69a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.69a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/4 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      298.00
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.749
_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    -21.00  37.00   0.50    3.55    --    5.83 -99.00-120.00  116
  2  \w      2.00  38.00   0.50    3.55    --    5.83 -99.00  30.00   72
  3  \w    -22.00  21.00   0.50    3.55    --    5.83-100.00 111.00   86
  4  \w    -12.00  14.00   0.50    3.55    --    5.83 100.00-143.00   52
  5  \w    -38.00  22.00   0.50    3.55    --   -5.68 100.00-143.00  120
  6  \w     -4.00  62.00   0.50    3.55    --   -5.68  38.00-180.00  132
  7  \w    -23.00  24.00   0.50    3.55    --   -5.68 -99.00  60.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0538
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.749
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            20045
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.749
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.121
_diffrn_reflns_theta_min         3.301
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50621
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.69a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_description       plate
_exptl_crystal_F_000             704
_exptl_crystal_preparation       none
_exptl_crystal_recrystallization_method none
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     459
_refine_ls_number_reflns         8249
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0958
_refine_ls_R_factor_gt           0.0492
_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^)+(0.0594P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1181
_refine_ls_wR_factor_ref         0.1347
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4665
_reflns_number_total             8249
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01997g2.cif
_cod_data_source_block           gpy-36_auto
_cod_depositor_comments          'Adding full bibliography for 7159790.cif.'
_cod_database_code               7159790
_shelx_shelxl_version_number     2016/4
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.973
_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 Me refined with riding coordinates:
 C014(H01J,H01K,H01L), C015(H01A,H01B,H01C), C019(H01M,H01N,H01O), C01E(H01G,
 H01H,H01I)
2.b Aromatic/amide H refined with riding coordinates:
 C00O(H00O), C00R(H00R), C00S(H00S), C00T(H00T), C00U(H00U), C00W(H00W),
 C00X(H00X), C00Y(H00Y), C010(H010), C011(H011), C012(H012), C013(H013),
 C016(H016), C018(H018), C01A(H01D), C01B(H01E), C01C(H01P), C01D(H01F)
;
_shelx_res_checksum              91649
_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
;