Transition metal-free one-pot tandem chemoselective reduction and cyclization of 3/5-(2-nitrophenyl)-1<i>H</i>-pyrazoles using sodium dithionite.
Srikanth, Danaboina; Shejul, Gayatri Diliprao; Joshi, Swanand Vinayak; Kalam, Abdul; Jahnavi, Avvaru Subha; Dikundwar, Amol G.; Chopra, Sidharth; Yaddanapudi, Madhavi Venkata; Nanduri, Srinivas; Organic & biomolecular chemistry 23 (2025) 5812–5820; doi:10.1039/d5ob00610d

data_7160566
_publ_section_title
;
 Transition metal-free one-pot tandem chemoselective reduction and
 cyclization of 3/5-(2-nitrophenyl)-1<i>H</i>-pyrazoles using sodium
 dithionite.
;
_journal_issue                   24
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5812
_journal_page_last               5820
_journal_paper_doi               10.1039/d5ob00610d
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C23 H19 N3 O'
_chemical_formula_sum            'C23 H19 N3 O'
_chemical_formula_weight         353.41
_chemical_name_common            3l
_chemical_name_systematic
2-(4-methoxyphenyl)-5-phenyl-5,6-dihydropyrazolo[1,5-c]quinazoline
_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
_audit_creation_date             2025-03-06
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-03-10 deposited with the CCDC.	2025-05-21 downloaded from the CCDC.
;
_cell_angle_alpha                71.107(3)
_cell_angle_beta                 77.855(3)
_cell_angle_gamma                71.037(3)
_cell_formula_units_Z            4
_cell_length_a                   11.5160(10)
_cell_length_b                   13.0682(12)
_cell_length_c                   13.6833(14)
_cell_measurement_reflns_used    9909
_cell_measurement_temperature    298
_cell_measurement_theta_max      23.581
_cell_measurement_theta_min      2.236
_cell_volume                     1829.8(3)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298
_diffrn_detector                 'Bruker Photon III C14 CPAD detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0604
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            74168
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.987
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.39
_diffrn_source_power             0.0695
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7105
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1311 before and 0.0630 after correction.
The Ratio of minimum to maximum transmission is 0.9529.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear yellowish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_preparation
'Pre-heated ethanol is added to solubulize the solid compound and cooled down at room temperature'
_exptl_crystal_recrystallization_method
'The saturated ethanol solution was subjected for slow solvent evaporation excpecting the formation of single crystal'
_exptl_crystal_size_max          0.694
_exptl_crystal_size_mid          0.203
_exptl_crystal_size_min          0.095
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     489
_refine_ls_number_reflns         6439
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0470
_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^)+(0.0845P)^2^+0.2241P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1427
_refine_ls_wR_factor_ref         0.1563
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5043
_reflns_number_total             6439
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00610d2.cif
_cod_data_source_block           3l
_cod_depositor_comments          'Adding full bibliography for 7160566.cif.'
_cod_database_code               7160566
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.946
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C8(H8), C8(H8)
1.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C6(H6), C5(H5), C4(H4), C3(H3), C9(H9), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C22(H22), C21(H21), C19(H19), C18(H18), C3(H3), C4(H4),
 C5(H5), C6(H6), N1(H1), C9(H9), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C18(H18), C19(H19), C21(H21), C22(H22)
1.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C23(H23A,H23B,H23C)
;
_olex2_exptl_crystal_mounting_method
'A fine quality crystal was isolated and loaded on 0.3 mm nylon cryloop using paratone oil and the data was collected at room temperature'
_olex2_submission_original_sample_id 3l
_olex2_submission_special_instructions 'No special instructions were received'