Design, synthesis, and apoptotic evaluation of spiro[indoline-3,3'-pyrazolo[1,2-<i>a</i>]indazole] derivatives <i>via</i> [3 + 2] <i>N</i>,<i>N</i>-cycloaddition.
Thrinadh Kumar, Rapeti; Mulani, Sohel C.; Anwar, Shaik; Kottalanka, Ravi K.; Organic & biomolecular chemistry 23 (2025) 3583–3589; doi:10.1039/d5ob00049a

data_7160403
_publ_section_title
;
 Design, synthesis, and apoptotic evaluation of
 spiro[indoline-3,3'-pyrazolo[1,2-<i>a</i>]indazole] derivatives
 <i>via</i> [3 + 2] <i>N</i>,<i>N</i>-cycloaddition.
;
_journal_issue                   15
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3583
_journal_page_last               3589
_journal_paper_doi               10.1039/d5ob00049a
_journal_volume                  23
_journal_year                    2025
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C22 H14 F3 N5 O2'
_chemical_formula_sum            'C22 H14 F3 N5 O2'
_chemical_formula_weight         437.38
_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     dual
_audit_creation_date             2023-10-31
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_audit_update_record
;
2024-04-08 deposited with the CCDC.	2025-03-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.798(3)
_cell_length_b                   11.682(4)
_cell_length_c                   16.946(5)
_cell_measurement_reflns_used    9975
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.00
_cell_measurement_theta_min      2.24
_cell_volume                     2137.6(11)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      298.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0571
_diffrn_reflns_av_unetI/netI     0.0483
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            48768
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_min         2.117
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6505
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1396 before and 0.0722 after correction.
The Ratio of minimum to maximum transmission is 0.8725.
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    1.359
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.213
_exptl_crystal_size_mid          0.211
_exptl_crystal_size_min          0.194
_refine_diff_density_max         0.694
_refine_diff_density_min         -0.797
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details
;
 Flack x determined using 1174 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.234
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3900
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.234
_refine_ls_R_factor_all          0.1010
_refine_ls_R_factor_gt           0.0882
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2741
_refine_ls_wR_factor_ref         0.2903
_reflns_Friedel_coverage         0.753
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3176
_reflns_number_total             3900
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00049a2.cif
_cod_data_source_block           exter123_0m
_cod_depositor_comments          'Adding full bibliography for 7160403.cif.'
_cod_original_cell_volume        2137.7(10)
_cod_database_code               7160403
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.977
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C21) = Uanis(C20) = Uanis(C19)
Uanis(F2) = Uanis(F1)
3.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B)
3.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C13(H13), C3(H3), C14(H14), C6(H6), C5(H5), C4(H4), C20(H20)
3.c X=CH2 refined with riding coordinates:
 N3(H3A,H3B), C21(H21A,H21B)
;
_shelx_res_checksum              73790
_olex2_submission_special_instructions 'No special instructions were received'