Synthesis of triazole-fused tetracyclic spirooxindole derivatives <i>via</i> metal-free Huisgen cycloaddition.
Maiti, Sandip; Parui, Nabin; Halder, Joydev; Dash, Jyotirmayee; Chemical communications (Cambridge, England) 60 (2024) 10009–10012; doi:10.1039/d4cc02534b

data_7133458
_publ_section_title
;
 Synthesis of triazole-fused tetracyclic spirooxindole derivatives
 <i>via</i> metal-free Huisgen cycloaddition.
;
_journal_issue                   73
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              10009
_journal_page_last               10012
_journal_paper_doi               10.1039/d4cc02534b
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C17 H18 N4 O'
_chemical_formula_sum            'C17 H18 N4 O'
_chemical_formula_weight         294.35
_chemical_name_systematic        Spirooxindole2
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2024-02-05
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2024-05-17 deposited with the CCDC.	2024-07-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.630(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.422(4)
_cell_length_b                   20.895(10)
_cell_length_c                   7.919(4)
_cell_measurement_reflns_used    5827
_cell_measurement_temperature    229.07
_cell_measurement_theta_max      28.378
_cell_measurement_theta_min      2.272
_cell_volume                     1493.8(12)
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      229.07
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 6000 area detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1031
_diffrn_reflns_av_unetI/netI     0.0890
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            16226
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.388
_diffrn_reflns_theta_min         2.256
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.2696
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1690 before and 0.1211 after correction.
The Ratio of minimum to maximum transmission is 0.3615.
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    1.309
_exptl_crystal_description       needle
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         3717
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0904
_refine_ls_R_factor_gt           0.0672
_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^)+(0.0902P)^2^+0.4189P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1686
_refine_ls_wR_factor_ref         0.1874
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2752
_reflns_number_total             3717
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc02534b2.cif
_cod_data_source_block           mo_jd260923_0m
_cod_depositor_comments
'Adding full bibliography for 7133457--7133458.cif.'
_cod_original_cell_volume        1493.7(13)
_cod_database_code               7133458
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.982
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C9(H9A,H9B), C10(H10A,H10B), C12(H12A,H12B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C5(H5), C14(H14), C6(H6), C16(H16)
;
_shelx_res_checksum              68285
_shelx_hkl_checksum              10146
_olex2_submission_special_instructions 'No special instructions were received'