Stereoselective One-Pot Synthesis of Spiro-Indenoquinoxaline-Pyrrolidine Hybrids: Structural Elucidation and Biological Evaluation
Shanmugam, Sivakumar; Ajaydev, Rameshbabu; Joy, Wilson; Krishnan, Aravind; New Journal of Chemistry  (2026) –; doi:10.1039/D6NJ00925E

data_7064361
_publ_section_title
;
 Stereoselective one-pot synthesis of spiro-indenoquinoxaline--pyrrolidine
 hybrids: structural elucidation and biological evaluation
;
_journal_issue                   20
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              8573
_journal_page_last               8580
_journal_paper_doi               10.1039/D6NJ00925E
_journal_volume                  50
_journal_year                    2026
_chemical_formula_moiety         'C32 H28.447 N3 O2 S2, 0.2[H2O]'
_chemical_formula_sum            'C32 H28.85 N3 O2.2 S2'
_chemical_formula_weight         554.75
_space_group_crystal_system      tetragonal
_space_group_IT_number           82
_space_group_name_Hall           'I -4'
_space_group_name_H-M_alt        'I -4'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-11-21
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7317)
;
_audit_update_record
;
2025-11-22 deposited with the CCDC.	2026-03-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.317(5)
_cell_length_b                   22.317(5)
_cell_length_c                   11.022(4)
_cell_measurement_reflns_used    9723
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      23.45
_cell_measurement_theta_min      2.58
_cell_volume                     5489(3)
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      300.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            67142
_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         28.291
_diffrn_reflns_theta_min         2.061
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            gold
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_description       block
_exptl_crystal_F_000             2332
_exptl_crystal_size_max          0.317
_exptl_crystal_size_mid          0.276
_exptl_crystal_size_min          0.161
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
;
 Flack x determined using 1707 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.029(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.162
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     374
_refine_ls_number_reflns         6834
_refine_ls_number_restraints     17
_refine_ls_restrained_S_all      1.165
_refine_ls_R_factor_all          0.1238
_refine_ls_R_factor_gt           0.0648
_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^)+(0.1145P)^2^+2.9162P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1644
_refine_ls_wR_factor_ref         0.2367
_reflns_Friedel_coverage         0.901
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                4194
_reflns_number_total             6834
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6nj00925e3.cif
_cod_data_source_block           6e_110925_a
_cod_depositor_comments          'Adding full bibliography for 7064361.cif.'
_cod_original_cell_volume        5490(3)
_cod_original_formula_sum        'C32 H28.85 N3 O2.20 S2'
_cod_database_code               7064361
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.964
_shelx_estimated_absorpt_t_min   0.931
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C00D-C00H \\sim C00D-C4
 with sigma of 0.02
 C00W-O011 \\sim C3-O0
 with sigma of 0.02
 C00D-C00R \\sim C00D-C1
 with sigma of 0.02
 C00H-O011 \\sim C4-O0
 with sigma of 0.04
 C00Z-O011 \\sim C2-O0
 with sigma of 0.04
 C00H-C00W \\sim C4-C3
 with sigma of 0.02
 C00R-C012 \\sim C1-C0
 with sigma of 0.02
 C00W-C00Z \\sim C3-C2
 with sigma of 0.02
 C00Z-C012 \\sim C2-C0
 with sigma of 0.02
 C00B-C00H \\sim C00B-C4
 with sigma of 0.04
 C00B-C00R \\sim C00B-C1
 with sigma of 0.04
 C00D-C00W \\sim C00D-C3
 with sigma of 0.04
 C00D-C012 \\sim C00D-C0
 with sigma of 0.04
 C00H-C00R \\sim C4-C1
 with sigma of 0.04
 C00H-C00Z \\sim C4-C2
 with sigma of 0.04
 C00R-C00Z \\sim C1-C2
 with sigma of 0.04
 C00W-C012 \\sim C3-C0
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(O011) = Uanis(O0)
Uanis(C2) = Uanis(C00Z)
Uanis(C0) = Uanis(C012)
Uanis(C00W) = Uanis(C3)
Uanis(C00H) = Uanis(C4)
Uanis(C00R) = Uanis(C1)
4. Others
 Sof(C1)=Sof(H1)=Sof(C0)=Sof(H0)=Sof(C2)=Sof(H2)=Sof(C3)=Sof(C4)=Sof(H4)=
 Sof(O0)=Sof(H0A)=1-FVAR(1)
 Sof(C00H)=Sof(H00H)=Sof(C00R)=Sof(H00R)=Sof(C00W)=Sof(C00Z)=Sof(H00Z)=
 Sof(O011)=Sof(C012)=Sof(H012)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C00A(H00A), C00B(H00B), C00K(H00K)
5.b Secondary CH2 refined with riding coordinates:
 C00M(H00C,H00D), C00O(H00E,H00F), C00S(H00G,H00I)
5.c Aromatic/amide H refined with riding coordinates:
 C00H(H00H), C00J(H00J), C00L(H00L), C00N(H00N), C00P(H00P), C00R(H00R),
 C00T(H00T), C00U(H00U), C00V(H00V), C00X(H00X), C00Y(H00Y), C00Z(H00Z),
 C012(H012), C1(H1), C0(H0), C2(H2), C4(H4)
5.d Idealised Me refined as rotating group:
 C010(H01A,H01B,H01C), C014(H01D,H01E,H01F)
5.e Idealised tetrahedral OH refined as rotating group:
 O0(H0A)
;
_smtbx_masks_special_details
;
A solvent mask was calculated and 14 electrons were 
found in a volume of 66\%A^3^ in 1 void per unit cell. 
This is consistent with the presence of 
0.2[H2O] per Asymmetric Unit 
which account for 16 electrons 
per unit cell.
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              5762
_shelx_fab_checksum              96397
_olex2_submission_special_instructions 'No special instructions were received'