Synthesis of diarylsulphide-/diarylselenide-embedded pyrazole-fused isocoumarins and isatin/ninhydrin hydrazones <i>via</i> acid-catalyzed solvent- and temperature-controlled reactions.
Panja, Sayanwita; Dhurey, Arun; Pramanik, Animesh; Organic & biomolecular chemistry 23 (2025) 440–448; doi:10.1039/d4ob01422g

data_7160228
_publ_section_title
;
 Synthesis of diarylsulphide-/diarylselenide-embedded pyrazole-fused
 isocoumarins and isatin/ninhydrin hydrazones <i>via</i> acid-catalyzed
 solvent- and temperature-controlled reactions.
;
_journal_issue                   2
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              440
_journal_page_last               448
_journal_paper_doi               10.1039/d4ob01422g
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C30 H22 N2 O3 S'
_chemical_formula_sum            'C30 H22 N2 O3 S'
_chemical_formula_weight         490.55
_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             2024-06-28
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2024-07-18 deposited with the CCDC.	2024-11-11 downloaded from the CCDC.
;
_cell_angle_alpha                81.608(5)
_cell_angle_beta                 82.326(5)
_cell_angle_gamma                68.920(5)
_cell_formula_units_Z            2
_cell_length_a                   7.8820(11)
_cell_length_b                   10.6903(15)
_cell_length_c                   15.608(2)
_cell_measurement_reflns_used    5062
_cell_measurement_temperature    298.95
_cell_measurement_theta_max      28.90
_cell_measurement_theta_min      2.56
_cell_volume                     1209.3(3)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298.95
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0824
_diffrn_reflns_av_unetI/netI     0.1006
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15750
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.139
_diffrn_reflns_theta_min         2.648
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.170
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.3155
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1641 before and 0.0981 after correction.
The Ratio of minimum to maximum transmission is 0.4230.
The \l/2 correction factor is Not present.
;
_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    1.347
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       0.035(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         6425
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.1222
_refine_ls_R_factor_gt           0.0722
_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^)+(0.1109P)^2^+0.1566P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1890
_refine_ls_wR_factor_ref         0.2350
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3718
_reflns_number_total             6425
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01422g2.cif
_cod_data_source_block           arunap
_cod_depositor_comments
'Adding full bibliography for 7160227--7160228.cif.'
_cod_database_code               7160228
_shelx_shelxl_version_number     2016/6
_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 Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13), C15(H15), C16(H16),
 C19(H19), C20(H20), C22(H22), C23(H23), C25(H25), C26(H26), C28(H28), C29(H29)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C30(H30A,H30B,H30C)
;
_shelx_res_checksum              68196
_olex2_submission_special_instructions 'No special instructions were received'