Access to Isoxazolidines through Visible-Light-Induced Difunctionalization of Alkenes
Yang, Hui; Wei, Guo; Jiang, Zhiyong; ACS Catalysis 9 (2019) 9599–; doi:10.1021/acscatal.9b03567

data_4514621
_publ_section_title
;
 Access to Isoxazolidines through Visible-Light-Induced
 Difunctionalization of Alkenes
;
_journal_issue                   10
_journal_name_full               'ACS Catalysis'
_journal_page_first              9599
_journal_paper_doi               10.1021/acscatal.9b03567
_journal_volume                  9
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H16 N2 O3'
_chemical_formula_sum            'C18 H16 N2 O3'
_chemical_formula_weight         308.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_space_group_name_H-M   'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-12-12
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 105.131(12)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.4615(14)
_cell_length_b                   5.5002(6)
_cell_length_c                   12.6887(13)
_cell_measurement_reflns_used    1237
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      60.9860
_cell_measurement_theta_min      3.9930
_cell_volume                     772.17(16)
_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    'ShelXT (Sheldrick, 2015)'
_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  -49.00   37.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000  -30.0000 86

  2 omega -108.00  -32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000   60.0000 76

  3 omega  -52.00   35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   57.0000   30.0000 87

  4 omega   43.00  107.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000 -150.0000 64

  5 omega    3.00   30.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000  -90.0000 27

  6 omega   -1.00   50.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  120.0000 51

  7 omega   -4.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000   60.0000 79

  8 omega   34.00   62.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000    0.0000 28

  9 omega   51.00   99.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 48

 10 omega   62.00  136.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000  -30.0000 74

 11 omega   46.00  106.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   60.0000 60

 12 omega   93.00  156.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  150.0000 63

 13 omega   38.00   86.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 48

 14 omega   44.00  115.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000    0.0000 71

 15 omega   40.00   91.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 51

 16 omega  142.00  174.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -60.0000 32

 17 omega   91.00  127.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -60.0000 36

 18 omega  -85.00  -59.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000  120.0000 26

 19 omega  -70.00  -44.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000  -90.0000 26

 20 omega    5.00   31.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   77.0000   90.0000 26

 21 omega  -52.00  -25.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   77.0000   90.0000 27

 22 omega    9.00   71.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000 -150.0000 62

 23 omega   27.00   98.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000   30.0000 71

 24 omega   36.00   62.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000   60.0000 26

 25 omega  140.00  174.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  150.0000 34

 26 omega   83.00  109.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 26

 27 omega  119.00  170.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -90.0000 51

 28 omega   39.00   79.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -30.0000 40

 29 omega  121.00  174.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -180.0000 53

 30 omega   82.00  107.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  120.0000 25

 31 omega   76.00  102.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  -30.0000 26

 32 omega   49.00   76.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 27

 33 omega  124.00  175.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  -30.0000 51

 34 omega   40.00   63.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 23
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0794927000
_diffrn_orient_matrix_UB_12      -0.2300327000
_diffrn_orient_matrix_UB_13      -0.0202959000
_diffrn_orient_matrix_UB_21      0.1134489000
_diffrn_orient_matrix_UB_22      -0.1595314000
_diffrn_orient_matrix_UB_23      0.0394549000
_diffrn_orient_matrix_UB_31      -0.0129184000
_diffrn_orient_matrix_UB_32      0.0137897000
_diffrn_orient_matrix_UB_33      0.1176153000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4791
_diffrn_reflns_point_group_measured_fraction_full 0.702
_diffrn_reflns_point_group_measured_fraction_max 0.702
_diffrn_reflns_theta_full        67.057
_diffrn_reflns_theta_max         67.057
_diffrn_reflns_theta_min         3.995
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.748
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98023
_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            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_description       prism
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.105
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details
;
 Flack x determined using 388 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         1934
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0400
_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^)+(0.0392P)^2^+0.0472P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0923
_refine_ls_wR_factor_ref         0.1018
_reflns_Friedel_coverage         0.400
_reflns_Friedel_fraction_full    0.402
_reflns_Friedel_fraction_max     0.402
_reflns_number_gt                1623
_reflns_number_total             1934
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b03567_si_002.cif
_cod_data_source_block           wg888
_cod_database_code               4514621
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C20H56N2O2
_reflns_odcompleteness_completeness 100.00
_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 C(H,H,H,H) groups
2. Restrained distances
 N2A-O3A
 1.4 with sigma of 0.02
 C13-N2A
 1.45 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(N2) = Uanis(N2A)
Uanis(O3) = Uanis(O3A)
4. Others
 Sof(H6BC)=Sof(H6BD)=Sof(N2A)=Sof(O3A)=1-FVAR(1)
 Sof(H6AA)=Sof(H6AB)=Sof(N2)=Sof(O3)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C5(H5A,H5B), C6(H6AA,H6AB), C6(H6BC,H6BD)
5.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18)
;
_olex2_submission_special_instructions 'No special instructions were received'