Regio- and stereoselective synthesis of spiropyrrolidine-oxindole and bis-spiropyrrolizidine-oxindole grafted macrocycles through [3 + 2] cycloaddition of azomethine ylides
Prabhakaran, Perumal; Rajakumar, Perumal; RSC Advances 10 (2020) 10263–10276; doi:10.1039/C9RA10463A

data_7240104
_publ_section_title
;
 Regio- and stereoselective synthesis of spiropyrrolidine-oxindole and
 bis-spiropyrrolizidine-oxindole grafted macrocycles through [3 + 2]
 cycloaddition of azomethine ylides
;
_journal_issue                   17
_journal_name_full               'RSC Advances'
_journal_page_first              10263
_journal_page_last               10276
_journal_paper_doi               10.1039/C9RA10463A
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C64 H56 Cl2 N10 O6, 2(C H Cl3)'
_chemical_formula_sum            'C66 H58 Cl8 N10 O6'
_chemical_formula_weight         1370.82
_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   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2019-07-04 deposited with the CCDC.	2020-02-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.339(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   16.8951(3)
_cell_length_b                   18.5524(3)
_cell_length_c                   10.2114(2)
_cell_measurement_reflns_used    9058
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      2.98
_cell_volume                     3181.14(10)
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3(Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_molecular_graphics
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
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_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker axs kappa apex3 CMOS Diffractometer'
_diffrn_measurement_method       '\w and \f scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            63080
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         3.170
_exptl_absorpt_coefficient_mu    0.416
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6643
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1416
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.668
_refine_diff_density_min         -0.698
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       0.0245(16)
_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   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     435
_refine_ls_number_reflns         5581
_refine_ls_number_restraints     72
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0556
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0541P)^2^+4.0760P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1332
_refine_ls_wR_factor_ref         0.1511
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4632
_reflns_number_total             5581
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ra10463a2.cif
_cod_data_source_block           P6
_cod_depositor_comments          'Adding full bibliography for 7240104.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7240104
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.940
_shelx_estimated_absorpt_t_max   0.960
_shelx_res_checksum              70804