N-heterocyclic carbene catalyzed [2 + 3] annulation reaction for the synthesis of trifluoroethyl 3,2'-spirooxindole γ-lactam.
Pu, Yiru; Wang, Maolin; Tian, Wanrong; Ge, Xian; Zhu, Dikai; Wang, Chuanqi; Zeng, Yingjie; Tao, Feiyan; Deng, Yun; Lu, Jun; RSC advances 14 (2024) 18453–18458; doi:10.1039/d4ra02252a

data_7248856
_publ_section_title
;
 N-heterocyclic carbene catalyzed [2 + 3] annulation reaction for the
 synthesis of trifluoroethyl 3,2'-spirooxindole &#x3b3;-lactam.
;
_journal_issue                   26
_journal_name_full               'RSC advances'
_journal_page_first              18453
_journal_page_last               18458
_journal_paper_doi               10.1039/d4ra02252a
_journal_volume                  14
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_sum            'C27 H22 Br F3 N2 O3'
_chemical_formula_weight         559.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2021-08-31 deposited with the CCDC.	2024-05-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.3130(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.3667(3)
_cell_length_b                   7.8133(2)
_cell_length_c                   14.3984(4)
_cell_measurement_reflns_used    9937
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.18
_cell_measurement_theta_min      3.18
_cell_volume                     1233.34(6)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_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           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            21753
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.262
_diffrn_reflns_theta_min         3.182
_exptl_absorpt_coefficient_mu    2.756
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             568
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.512
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 1804 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.019(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         4471
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.982
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0346
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1131
_refine_ls_wR_factor_ref         0.1171
_reflns_Friedel_coverage         0.835
_reflns_Friedel_fraction_full    0.981
_reflns_Friedel_fraction_max     0.977
_reflns_number_gt                4208
_reflns_number_total             4471
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ra02252a2.cif
_cod_data_source_block           20210830T37_0m_a
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7248856
_shelx_shelxl_version_number     2016/6
_shelx_res_checksum              43833
_shelx_hkl_checksum              38709