The asymmetric construction of CF<sub>3</sub>-containing spiro-thiazolone-pyrrolidine compounds via [3 + 2] cycloaddition.
Li, Boyu; Liu, Jikun; Gao, Fengyun; Sun, Mengmeng; Guo, Yifei; Zhou, Yuan; Wen, Dongwa; Deng, Yabo; Chen, Hui; Wang, Kairong; Yan, Wenjin; Organic & biomolecular chemistry 17 (2019) 2892–2895; doi:10.1039/c9ob00325h

data_7156701
_publ_section_title
;
 The asymmetric construction of CF<sub>3</sub>-containing
 spiro-thiazolone-pyrrolidine compounds via [3 + 2] cycloaddition.
;
_journal_issue                   11
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2892
_journal_page_last               2895
_journal_paper_doi               10.1039/c9ob00325h
_journal_volume                  17
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25 H22 Br F3 N2 O5 S'
_chemical_formula_sum            'C25 H22 Br F3 N2 O5 S'
_chemical_formula_weight         599.42
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-07-15
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2018-12-27 deposited with the CCDC.    2019-02-22 downloaded from the CCDC.
;
_cell_angle_alpha                97.287(5)
_cell_angle_beta                 100.642(5)
_cell_angle_gamma                93.026(5)
_cell_formula_units_Z            3
_cell_length_a                   12.4079(7)
_cell_length_b                   12.8250(7)
_cell_length_c                   12.9266(8)
_cell_measurement_reflns_used    2220
_cell_measurement_temperature    298.84(10)
_cell_measurement_theta_max      22.0250
_cell_measurement_theta_min      3.7300
_cell_volume                     1999.2(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298.84(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega   25.00   92.20   1.0500    5.0000
omega____ theta____ kappa____ phi______ frames
    -       23.0992   77.0000  -30.0000 64

  2 omega   46.00  102.70   1.0500    5.0000
omega____ theta____ kappa____ phi______ frames
    -       23.0992  178.0000    0.0000 54

  3 omega  -51.00   88.65   1.0500    5.0000
omega____ theta____ kappa____ phi______ frames
    -       23.0992  -19.0000    0.0000 133

  4 omega  -14.00   25.90   1.0500    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.0367  -99.0000  -30.0000 38

  5 omega  -12.00   60.45   1.0500    5.0000
omega____ theta____ kappa____ phi______ frames
    -       23.0992  -99.0000 -180.0000 69

  6 omega  -98.00  -71.75   1.0500    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.0367  178.0000    0.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0265067000
_diffrn_orient_matrix_UB_12      -0.0389998000
_diffrn_orient_matrix_UB_13      0.0274034000
_diffrn_orient_matrix_UB_21      -0.0342280000
_diffrn_orient_matrix_UB_22      0.0073716000
_diffrn_orient_matrix_UB_23      0.0382075000
_diffrn_orient_matrix_UB_31      -0.0391134000
_diffrn_orient_matrix_UB_32      -0.0394023000
_diffrn_orient_matrix_UB_33      -0.0311123000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_unetI/netI     0.0948
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13554
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.35
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.679
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67783
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
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    1.494
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.009(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1009
_refine_ls_number_reflns         10162
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.1146
_refine_ls_R_factor_gt           0.0553
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0232P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0815
_refine_ls_wR_factor_ref         0.1032
_reflns_number_gt                5877
_reflns_number_total             10162
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9ob00325h2.cif
_cod_data_source_block           sujh_0714
_cod_depositor_comments          'Adding full bibliography for 7156701.cif.'
_cod_database_code               7156701
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N6(H6), N4(H4)
2.b Ternary CH refined with riding coordinates:
 C60(H60), C61(H61), C35(H35), C36(H36), C10(H10), C11(H11)
2.c Secondary CH2 refined with riding coordinates:
 C65(H65A,H65B), C68(H68A,H68B), C39(H39A,H39B), C49(H49A,H49B), C14(H14A,
 H14B), C17(H17A,H17B)
2.d Aromatic/amide H refined with riding coordinates:
 C52(H52), C53(H53), C54(H54), C55(H55), C56(H56), C71(H71), C72(H72),
 C74(H74), C75(H75), C27(H27), C28(H28), C29(H29), C30(H30), C31(H31), C43(H43),
  C44(H44), C46(H46), C47(H47), C1(H1), C2(H2A), C3(H3), C4(H4A), C5(H5),
 C21(H21), C22(H22), C24(H24), C25(H25)
2.e Idealised Me refined as rotating group:
 C66(H66A,H66B,H66C), C69(H69A,H69B,H69C), C40(H40A,H40B,H40C), C50(H50A,H50B,
 H50C), C15(H15A,H15B,H15C), C18(H18A,H18B,H18C)
;
_olex2_date_sample_data_collection 2016-07-14
_olex2_submission_special_instructions 'No special instructions were received'