The catalytic asymmetric synthesis of CF<sub>3</sub>-containing spiro-oxindole-pyrrolidine-pyrazolone compounds through squaramide-catalyzed 1,3-dipolar cycloaddition.
Wang, Cui; Wen, Dongwa; Chen, Hui; Deng, Yabo; Liu, Xueting; Liu, Xin; Wang, Li; Gao, Fengyun; Guo, Yifei; Sun, Mengmeng; Wang, Kairong; Yan, Wenjin; Organic & biomolecular chemistry 17 (2019) 5514–5519; doi:10.1039/c9ob00720b

data_7156838
_publ_section_title
;
 The catalytic asymmetric synthesis of CF<sub>3</sub>-containing
 spiro-oxindole-pyrrolidine-pyrazolone compounds through
 squaramide-catalyzed 1,3-dipolar cycloaddition.
;
_journal_issue                   22
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5514
_journal_page_last               5519
_journal_paper_doi               10.1039/c9ob00720b
_journal_volume                  17
_journal_year                    2019
_chemical_absolute_configuration unk
_chemical_formula_sum            'C33 H23 Br F3 N4 O2'
_chemical_formula_weight         644.46
_space_group_crystal_system      monoclinic
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_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
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-12-26 deposited with the CCDC.    2019-05-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
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_cell_angle_gamma                90
_cell_formula_units_Z            2
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_cell_length_c                   17.6260(10)
_cell_measurement_reflns_used    9589
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      66.56
_cell_measurement_theta_min      2.51
_cell_volume                     1353.82(13)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART APEX II'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 'fine-focus sealed tube'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_diffrn_measurement_method       '\w scan'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_unetI/netI     0.0503
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
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_diffrn_reflns_theta_full        66.561
_diffrn_reflns_theta_max         66.561
_diffrn_reflns_theta_min         4.365
_exptl_absorpt_coefficient_mu    2.596
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_description       block
_exptl_crystal_F_000             654
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_transmission_factor_max   0.7452
_exptl_transmission_factor_min   0.3820
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 1972 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.014(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     389
_refine_ls_number_reflns         4680
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0282
_refine_ls_R_factor_gt           0.0270
_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^)+(0.0100P)^2^+0.3411P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0612
_refine_ls_wR_factor_ref         0.0621
_reflns_Friedel_coverage         0.825
_reflns_Friedel_fraction_full    0.970
_reflns_Friedel_fraction_max     0.970
_reflns_number_gt                4544
_reflns_number_total             4680
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob00720b2.cif
_cod_data_source_block           20180118_WangCui_C33N4F3O2Br1H_0m_a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 7156837--7156839.cif.
;
_cod_original_cell_volume        1353.83(13)
_cod_database_code               7156838
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.510
_shelx_estimated_absorpt_t_max   0.625
_shelx_res_checksum              65245
_shelx_hkl_checksum              42791