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_7133457
_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         'C20 H18 N3.985 O2'
_chemical_formula_sum            'C20 H18 N4 O2'
_chemical_formula_weight         346.38
_chemical_name_systematic        SPIROOXINDOLE1
_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   mixed
_audit_creation_date             2024-03-18
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.083(15)
_cell_length_b                   19.232(17)
_cell_length_c                   5.595(5)
_cell_measurement_reflns_used    7252
_cell_measurement_temperature    169.04
_cell_measurement_theta_max      25.62
_cell_measurement_theta_min      2.46
_cell_volume                     1731(3)
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      169.04
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 6000 area detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0787
_diffrn_reflns_av_unetI/netI     0.0521
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            17927
_diffrn_reflns_point_group_measured_fraction_full 0.900
_diffrn_reflns_point_group_measured_fraction_max 0.893
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.711
_diffrn_reflns_theta_min         2.468
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7448
_exptl_absorpt_correction_T_min  0.6273
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1387 before and 0.0969 after correction.
The Ratio of minimum to maximum transmission is 0.8422.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            clear
_exptl_crystal_colour_lustre     clear
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_description       needle
_exptl_crystal_F_000             728
_exptl_crystal_preparation       'Slow evaporation'
_exptl_crystal_recrystallization_method methanol
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 878 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(10)
_refine_ls_extinction_coef       0.041(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         2941
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0384
_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^)+(0.0339P)^2^+0.3624P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0895
_refine_ls_wR_factor_ref         0.1001
_reflns_Friedel_coverage         0.622
_reflns_Friedel_fraction_full    0.783
_reflns_Friedel_fraction_max     0.769
_reflns_number_gt                2497
_reflns_number_total             2941
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc02534b2.cif
_cod_data_source_block           mo_jd090823_0m_a
_cod_depositor_comments
'Adding full bibliography for 7133457--7133458.cif.'
_cod_database_code               7133457
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.982
_olex2_refinement_description
;
1.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C14(H14A,H14B)
1.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C11(H11), C16(H16), C10(H10), C20(H20), C19(H19), C17(H17), C18(H18)
1.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_shelx_res_checksum              29032
_shelx_hkl_checksum              58642
_olex2_submission_special_instructions 'No special instructions were received'