Design and synthesis of spirooxindole–pyrrolidines embedded with indole and pyridine heterocycles by multicomponent reaction: anticancer and in silico studies
Mayakrishnan, Sivakalai; Kathirvelan, Devarajan; Arun, Yuvaraj; Saranraj, Krishnan; Balachandran, Chandrasekaran; Aoki, Shin; Yuvaraj, Pannerselvam; Maheswarai, Narayanan Uma; New Journal of Chemistry 46 (2022) 10089–10106; doi:10.1039/D1NJ05839H

data_7061475
_publ_section_title
;
 Design and synthesis of spirooxindole--pyrrolidines embedded with indole
 and pyridine heterocycles by multicomponent reaction: anticancer and in
 silico studies
;
_journal_issue                   21
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              10089
_journal_page_last               10106
_journal_paper_doi               10.1039/D1NJ05839H
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         '2(C27 H20 F N5 O2)'
_chemical_formula_sum            'C54 H40 F2 N10 O4'
_chemical_formula_weight         930.96
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2021-12-23
_audit_creation_method
;
Olex2 1.5-dev
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6396)
;
_audit_update_record
;
2022-04-23 deposited with the CCDC.	2022-04-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.4758(10)
_cell_length_b                   11.0289(8)
_cell_length_c                   24.904(2)
_cell_measurement_reflns_used    9997
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.67
_cell_measurement_theta_min      2.22
_cell_volume                     4525.3(6)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.5-dev (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-dev (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_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  0.0459
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            51470
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.533
_diffrn_reflns_theta_min         2.019
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6812
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0863 before and 0.0525 after correction.
The Ratio of minimum to maximum transmission is 0.9141.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1936
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 2433 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(4)
_refine_ls_extinction_coef       0.0019(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     635
_refine_ls_number_reflns         8422
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0770
_refine_ls_R_factor_gt           0.0463
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0450P)^2^+1.2155P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1143
_reflns_Friedel_coverage         0.948
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                6237
_reflns_number_total             8422
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1nj05839h2.cif
_cod_data_source_block           3pcc5
_cod_depositor_comments
'Adding full bibliography for 7061475--7061476.cif.'
_cod_database_code               7061475
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.972
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Shared sites
{N24, C24}
{C22, N22}
3. Uiso/Uaniso restraints and constraints
Uanis(N24) = Uanis(C24)
Uanis(C22) = Uanis(N22)
4. Others
 Sof(C24)=Sof(H24)=Sof(N22)=1-FVAR(1)
 Sof(C22)=Sof(H22)=Sof(N24)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C13(H13), C43(H43)
5.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C44(H44A,H44B)
5.c Aromatic/amide H refined with riding coordinates:
 N5(H5), N8(H8A), C3(H3), C2(H2), C10(H10), C11(H11), C16(H16), C17(H17),
 N18(H18), C21(H21), C22(H22), C23(H23), C25(H25), N27(H27), C29(H29), C30(H30),
  C31(H31), C32(H32), C38(H38), C39(H39), C40(H40), C41(H41), C48(H48),
 C49(H49), C50(H50), C53(H53), C5AA(H5AA), C8(H8), C24(H24)
5.d Idealised Me refined as rotating group:
 C46(H46A,H46B,H46C), C3AA(H3AA,H3AB,H3AC)
;
_shelx_res_checksum              29142
_olex2_submission_special_instructions 'No special instructions were received'