Asymmetric [3 + 2] photocycloadditions of cyclopropylamines with electron-rich and electron-neutral olefins
Dai, Yating; Liang, Shuangshuang; Zeng, Guangkuo; Huang, Hongchun; Zhao, Xiaowei; Cao, Shanshan; Jiang, Zhiyong; Chemical Science  (2022) –; doi:10.1039/D1SC07044D

data_1566587
_publ_section_title
;
 Asymmetric [3 + 2] photocycloadditions of cyclopropylamines with
 electron-rich and electron-neutral olefins
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC07044D
_journal_year                    2022
_chemical_formula_moiety         'C25 H21 F3 N2 O3 S'
_chemical_formula_sum            'C25 H21 F3 N2 O3 S'
_chemical_formula_weight         486.50
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-04-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-04-27 deposited with the CCDC.	2022-03-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 116.0951(19)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.2479(2)
_cell_length_b                   19.58181(19)
_cell_length_c                   16.7407(3)
_cell_measurement_reflns_used    12733
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.7330
_cell_measurement_theta_min      3.9340
_cell_volume                     4488.95(13)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega  -47.00  -18.00   0.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   57.0000  150.0000 58

  2 omega  -63.00  -15.00   0.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000    0.0000 96

  3 omega  -41.00  -15.00   0.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   57.0000  -30.0000 52

  4 omega -104.00  -54.00   0.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -37.0000  -30.0000 100

  5 omega    3.00   29.00   0.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   57.0000  150.0000 52

  6 omega  -26.00    0.00   0.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000  -30.0000 52

  7 omega -101.00  -75.00   0.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000    0.0000 52

  8 omega   -1.00   29.00   0.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000   60.0000 60

  9 omega  -34.00   18.00   0.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000  -60.0000 104

 10 omega   57.00   82.00   0.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000    0.0000 50

 11 omega   11.00   86.00   0.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000   60.0000 150

 12 omega   63.00  101.00   0.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -90.0000 76

 13 omega   41.00   66.00   0.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000   60.0000 50

 14 omega   26.00   57.00   0.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000  -60.0000 62

 15 omega   10.00   64.00   0.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  -90.0000 108

 16 omega   78.00  104.00   0.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  -90.0000 52

 17 omega    3.00   76.00   0.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000   30.0000 146

 18 omega   -4.00   29.00   0.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  120.0000 66

 19 omega   59.00   85.00   0.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -150.0000 52

 20 omega   41.00  107.00   0.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000  150.0000 132

 21 omega   -1.00   24.00   0.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  -90.0000 50

 22 omega   44.00   75.00   0.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  -90.0000 62

 23 omega  -27.00   54.00   0.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000 -150.0000 162

 24 omega   90.00  115.00   0.5000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   90.0000 50

 25 omega   40.00   91.00   0.5000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 102

 26 omega   63.00  178.00   0.5000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  -60.0000 230

 27 omega   38.00   99.00   0.5000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   60.0000 122

 28 omega   38.00   63.00   0.5000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 50

 29 omega   45.00  102.00   0.5000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -30.0000 114

 30 omega   88.00  128.00   0.5000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   60.0000 80

 31 omega   38.00  108.00   0.5000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 140

 32 omega  116.00  173.00   0.5000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -30.0000 114

 33 omega   76.00  113.00   0.5000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   30.0000 74

 34 omega  137.00  166.00   0.5000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   30.0000 58

 35 omega   37.00   67.00   0.5000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   30.0000 60

 36 omega   38.00   89.00   0.5000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  120.0000 102

 37 omega   55.00   99.00   0.5000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 88

 38 omega   84.00  141.00   0.5000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  120.0000 114

 39 omega   89.00  167.00   0.5000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000    0.0000 156

 40 omega   42.00   87.00   0.5000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 90

 41 omega   50.00  107.00   0.5000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  150.0000 114

 42 omega   50.00   76.00   0.5000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000    0.0000 52

 43 omega   89.00  115.00   0.5000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   30.0000 52

 44 omega  137.00  174.00   0.5000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   60.0000 74

 45 omega  152.00  178.00   0.5000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   94.0000  -52.0000 52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0299069000
_diffrn_orient_matrix_UB_12      0.0224622000
_diffrn_orient_matrix_UB_13      -0.0967049000
_diffrn_orient_matrix_UB_21      -0.0357767000
_diffrn_orient_matrix_UB_22      0.0688791000
_diffrn_orient_matrix_UB_23      0.0191190000
_diffrn_orient_matrix_UB_31      0.1024031000
_diffrn_orient_matrix_UB_32      0.0306482000
_diffrn_orient_matrix_UB_33      0.0279666000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            36582
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.079
_diffrn_reflns_theta_max         67.079
_diffrn_reflns_theta_min         3.707
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.779
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88415
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_description       prism
_exptl_crystal_F_000             2016
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     613
_refine_ls_number_reflns         8004
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0474
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0783P)^2^+1.2056P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1294
_refine_ls_wR_factor_ref         0.1377
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6721
_reflns_number_total             8004
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc07044d2.cif
_cod_data_source_block           zgk27039
_cod_original_cell_volume        4488.94(12)
_cod_database_code               1566587
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C20H20N4O4F3S1
_shelx_estimated_absorpt_t_max   0.842
_shelx_estimated_absorpt_t_min   0.776
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12), C12'(H12')
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C9'(H9'A,H9'B), C10'(H10C,H10D),
 C11'(H11C,H11D)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18), C20(H20), C21(H21), C23(H23), C24(H24), N2(H2), C3'(H3'), C4'(H4'),
 C5'(H5'), C6'(H6'), C14'(H14'), C15'(H15'), C16'(H16'), C17'(H17'), C18'(H18'),
  C20'(H20'), C21'(H21'), C23'(H23'), C24'(H24'), N2'(H2')
;
_olex2_submission_special_instructions 'No special instructions were received'