Diastereoselective [3+2] cycloaddition of 3-ylideneoxindoles with in situ generated CF2HCHN2: Syntheses of CF2H-containing spirooxindoles
Han, Wenyong; Zhao, Jia; Wang, Jian-Shu; Xiang, Guang-Yan; Zhang, Ding-Lei; Bai, Mei; Cui, Baodong; Wan, Nanwei; Chen, Yongzheng; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB01266G

data_7155676
_publ_section_title
;
 Diastereoselective [3+2] cycloaddition of 3-ylideneoxindoles with in situ
 generated CF2HCHN2: Syntheses of CF2H-containing spirooxindoles
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB01266G
_journal_year                    2017
_chemical_formula_sum            'C15 H15 F2 N3 O3'
_chemical_formula_weight         323.30
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-02-13 deposited with the CCDC.
2017-06-13 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 105.614(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.1037(4)
_cell_length_b                   18.2464(8)
_cell_length_c                   9.7398(5)
_cell_measurement_reflns_used    7870
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.68
_cell_measurement_theta_min      3.11
_cell_volume                     1558.17(13)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  CCD
_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  0.0356
_diffrn_reflns_av_sigmaI/netI    0.0277
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            23667
_diffrn_reflns_theta_full        27.55
_diffrn_reflns_theta_max         27.55
_diffrn_reflns_theta_min         3.11
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.9799
_exptl_absorpt_correction_T_min  0.9755
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         3589
_refine_ls_number_restraints     87
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0879
_refine_ls_R_factor_gt           0.0483
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0643P)^2^+0.2630P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1174
_refine_ls_wR_factor_ref         0.1355
_reflns_number_gt                2213
_reflns_number_total             3589
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ob01266g2.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7155676