DBU-catalyzed diastereoselective 1,3-dipolar [3+2] cycloaddition of trifluoroethyl amine-derived isatin ketimines with chalcones: synthesis of 5′-CF3-substituted 3,2′-pyrrolidinyl spirooxindoles
Zhou, Feng-Ji; Zhu, Bao-Lei; Huang, Zhen-Hui; Lin, Ning; Zhang, Zhen-Wei; RSC Advances 14 (2024) 548–551; doi:10.1039/D3RA08127C

data_7247936
_publ_section_title
;
 DBU-catalyzed diastereoselective 1,3-dipolar [3+2] cycloaddition of
 trifluoroethyl amine-derived isatin ketimines with chalcones: synthesis
 of 5&#x2032;-CF3-substituted 3,2&#x2032;-pyrrolidinyl spirooxindoles
;
_journal_issue                   1
_journal_name_full               'RSC Advances'
_journal_page_first              548
_journal_page_last               551
_journal_paper_doi               10.1039/D3RA08127C
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         'C25 H19 F3 N2 O2'
_chemical_formula_sum            'C25 H19 F3 N2 O2'
_chemical_formula_weight         436.44
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_atom_sites_solution_primary     iterative
_audit_block_doi                 10.5517/ccdc.csd.cc2hk137
_audit_creation_date             2020-05-10
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2023-11-25 deposited with the CCDC.	2023-12-12 downloaded from the CCDC.
;
_cell_angle_alpha                89.5519(19)
_cell_angle_beta                 87.0296(19)
_cell_angle_gamma                76.7371(18)
_cell_formula_units_Z            4
_cell_length_a                   11.3419(6)
_cell_length_b                   12.6437(7)
_cell_length_c                   15.4793(9)
_cell_measurement_reflns_used    9891
_cell_measurement_theta_max      23.782
_cell_measurement_theta_min      3.004
_cell_volume                     2157.7(2)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_measured_fraction_theta_full 0.9945
_diffrn_measured_fraction_theta_max 0.9945
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71076
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_unetI/netI     0.0535
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            46494
_diffrn_reflns_theta_full        27.6287
_diffrn_reflns_theta_max         27.63
_diffrn_reflns_theta_min         3.11
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7043
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0601 before and 0.0543 after correction.
The Ratio of minimum to maximum transmission is 0.9446.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.3434
_exptl_crystal_F_000             904.5670
_exptl_crystal_size_max          0.365
_exptl_crystal_size_mid          0.296
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.6814
_refine_diff_density_min         -0.5658
_refine_diff_density_rms         0.1489
_refine_ls_d_res_high            0.7663
_refine_ls_d_res_low             6.5577
_refine_ls_goodness_of_fit_ref   1.0546
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    76
_refine_ls_number_parameters     577
_refine_ls_number_reflns         9999
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0546
_refine_ls_R_factor_all          0.1225
_refine_ls_R_factor_gt           0.0635
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0850P)^2^+0.5600P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1481
_refine_ls_wR_factor_ref         0.1810
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              14
_reflns_limit_h_min              -14
_reflns_limit_k_max              16
_reflns_limit_k_min              -16
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                5888
_reflns_number_total             9999
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d3ra08127c2.cif
_cod_data_source_block           CHENQ505_2_0M
_cod_depositor_comments
;

2025-03-29
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C100 H76 F12 N8 O8'
_cod_original_formula_weight         1745.75
_cod_original_formula_moiety         '4(C25 H19 F3 N2 O2)'
_cod_original_formula_units_Z            1
_cod_database_code               7247936
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Riding coordinates:
 N4(H4), N2(H2)
2.b Ternary CH refined with riding coordinates:
 C36(H36), C9(H9), C35(H35), C34(H34), C10(H10), C11(H11)
2.c Aromatic/amide H refined with riding coordinates:
 C29(H29), C30(H30), C31(H31), C32(H32), C49(H49), C48(H48), C47(H47),
 C46(H46), C45(H45), C39(H39), C40(H40), C41(H41), C42(H42), C43(H43), C14(H14),
  C15(H15), C16(H16), C17(H17), C18(H18), C4(H4a), C5(H5), C6(H6), C7(H7),
 C24(H24), C23(H23), C22(H22), C21(H21), C20(H20), N3(H3), N1(H1)
;
_olex2_submission_special_instructions 'No special instructions were received'