The asymmetric synthesis of CF3-containing spiro[pyrrolidin-3,2'-oxindole] through the organocatalytic 1,3-dipolar cycloaddition reaction
Mingxia Ma; Yuanyuan Zhu; Quantao Sun; Xiaoyuan Li; Jinhuan Su; Long Zhao; Yanyan Zhao; Shuai Qiu; Wenjin Yan; Kairong Wang; Rui Wang; Chem.Commun. 51 (2015) 8789–; doi:10.1039/C4cc10216A

data_7117154
_publ_section_title
;
 The asymmetric synthesis of CF3-containing
 spiro[pyrrolidin-3,2'-oxindole] through the organocatalytic 1,3-dipolar
 cycloaddition reaction
;
_journal_name_full               Chem.Commun.
_journal_page_first              8789
_journal_paper_doi               10.1039/C4cc10216A
_journal_volume                  51
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H16 Cl F3 N2 O2'
_chemical_formula_sum            'C20 H16 Cl F3 N2 O2'
_chemical_formula_weight         408.80
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-12-26
_audit_creation_method
;
Olex2 1.2
(compiled Dec 5 2012 16:20:19, GUI svn.r4385)
;
_audit_update_record
;
2013-01-09 deposited with the CCDC.
2015-04-17 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 93.069(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.4449(8)
_cell_length_b                   7.9864(6)
_cell_length_c                   11.2224(9)
_cell_measurement_reflns_used    1381
_cell_measurement_temperature    292.88(10)
_cell_measurement_theta_max      28.5674
_cell_measurement_theta_min      3.1259
_cell_volume                     934.80(13)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      292.88(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9976
_diffrn_measured_fraction_theta_max 0.9756
_diffrn_measurement_details
;
1 omega -18.00 16.00 1.0000 5.0000
omega____ theta____ kappa____ phi______ frames
- -19.1930 19.0000 -60.0000 34

2 omega -10.00 94.00 1.0000 5.0000
omega____ theta____ kappa____ phi______ frames
- 22.6305 77.0000 90.0000 104

3 omega -45.00 46.00 1.0000 5.0000
omega____ theta____ kappa____ phi______ frames
- 22.6305 -57.0000 -60.0000 91
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0150587000
_diffrn_orient_matrix_UB_12      -0.0529196000
_diffrn_orient_matrix_UB_13      0.0481085000
_diffrn_orient_matrix_UB_21      0.0257610000
_diffrn_orient_matrix_UB_22      -0.0694663000
_diffrn_orient_matrix_UB_23      -0.0299236000
_diffrn_orient_matrix_UB_31      0.0610645000
_diffrn_orient_matrix_UB_32      0.0163205000
_diffrn_orient_matrix_UB_33      0.0282652000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3944
_diffrn_reflns_theta_full        28.63
_diffrn_reflns_theta_max         28.63
_diffrn_reflns_theta_min         3.13
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.252
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.07(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3043
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0471
_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^)+(0.0395P)^2^+0.2122P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0958
_refine_ls_wR_factor_ref         0.1090
_reflns_number_gt                2524
_reflns_number_total             3043
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc10216a2.cif
_cod_data_source_block           wangd1215
_cod_original_cell_volume        934.80(12)
_cod_database_code               7117154
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
H20 of C20, H19 of C19, H18 of C18, H17 of C17, H10 of C10, H5 of C5, H4 of
C4, H2A of C2, H16 of C16, H14 of C14, H12 of C12, H11 of C11
At 1.5 times of:
{H9A,H9B,H9C} of C9
2.a Ternary CH refined with riding coordinates:
C10(H10), C11(H11), C12(H12)
2.b Aromatic/amide H refined with riding coordinates:
C2(H2A), C4(H4), C5(H5), C14(H14), C16(H16), C17(H17), C18(H18), C19(H19),
C20(H20)
2.c Idealised Me refined as rotating group:
C9(H9A,H9B,H9C)
;