Organocatalytic Enantioselective Vinylogous Aldol Reaction of 5-Alkyl-4-Nitroisoxazoles to Paraformaldehyde.
Zhu, Bo; Li, Fuyuan; Lu, Bohua; Chang, Junbiao; Jiang, Zhiyong; The Journal of organic chemistry 83 (2018) 11350–11358; doi:10.1021/acs.joc.8b01573

data_4035644
_publ_section_title
;
 Organocatalytic Enantioselective Vinylogous Aldol Reaction of
 5-Alkyl-4-Nitroisoxazoles to Paraformaldehyde.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11350
_journal_page_last               11358
_journal_paper_doi               10.1021/acs.joc.8b01573
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C13 H18 N2 O8 S4'
_chemical_formula_sum            'C13 H18 N2 O8 S4'
_chemical_formula_weight         458.53
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-05-27
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90.401(5)
_cell_angle_beta                 110.250(7)
_cell_angle_gamma                103.900(6)
_cell_formula_units_Z            2
_cell_length_a                   8.3349(7)
_cell_length_b                   11.2541(7)
_cell_length_c                   11.5632(8)
_cell_measurement_reflns_used    3366
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.5380
_cell_measurement_theta_min      4.0540
_cell_volume                     982.96(14)
_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
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_diffrn_measurement_details
;
  1 omega  -68.00   19.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  -30.0000 87

  2 omega  -17.00   28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  120.0000 45

  3 omega   32.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  120.0000 34

  4 omega  -92.00  -36.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000 -120.0000 56

  5 omega   -3.00   28.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       36.7015  -99.0000  150.0000 31

  6 omega   14.00   76.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       36.7015  -99.0000    0.0000 62

  7 omega  -30.00   17.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
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  8 omega  -31.00   -3.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
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  9 omega   -9.00   16.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       36.7015  108.0000   66.8661 25

 10 omega   -4.00   64.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       36.7015  -99.0000  120.0000 68

 11 omega   32.00   74.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       36.7015  -99.0000  150.0000 42

 12 omega    3.00   30.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       36.7015   86.0000  160.8793 27

 13 omega  -32.00   52.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       36.7015  -57.0000  -90.0000 84

 14 omega   18.00   64.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       36.7015  -77.0000 -150.0000 46

 15 omega    2.00   27.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       40.0000   95.0000  -84.8594 25

 16 omega    9.00   34.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       44.0000   89.0000 -126.4709 25

 17 omega   15.00   42.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       48.0000   85.0000  170.9353 27

 18 omega   13.00   38.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       48.0000   88.0000   -5.2766 25

 19 omega   16.00   41.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       48.0000   84.0000  -69.6659 25

 20 omega   20.00   45.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       52.0000   83.0000 -108.8930 25

 21 omega   20.00   45.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       52.0000   84.0000   75.2741 25

 22 omega   20.00   45.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       52.0000   83.0000   40.6348 25

 23 omega   27.00   53.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       56.0000   78.0000  -55.3039 26

 24 omega   27.00   98.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       56.0000   78.0000  134.4099 71

 25 omega   77.00  119.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       56.0000   74.0000 -163.7901 42

 26 omega   29.00   74.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       56.0000   74.0000 -163.7901 45

 27 omega   77.00  126.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       60.0000   72.0000 -106.9998 49

 28 omega   99.00  126.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       60.0000   69.0000    1.6854 27

 29 omega   78.00  111.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       60.0000   75.0000  -42.0253 33

 30 omega   39.00   90.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       60.0000   69.0000    1.6854 51

 31 omega   31.00   74.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       60.0000   79.0000   81.0094 43

 32 omega  101.00  126.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       60.0000   70.0000   73.2352 25

 33 omega   34.00   61.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       60.0000   72.0000 -106.9998 27

 34 omega   33.00   72.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       60.0000   75.0000  -42.0253 39

 35 omega   35.00   62.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       60.0000   70.0000   73.2352 27

 36 omega   65.00   91.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       88.0000   67.0000 -115.1141 26

 37 omega  115.00  157.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       88.0000   53.0000 -179.7045 42

 38 omega   69.00  110.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       88.0000   53.0000 -179.7045 41

 39 omega   67.00   94.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       92.0000   71.0000   97.9760 27

 40 omega   79.00  105.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 26

 41 omega   88.00  124.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -30.0000 36

 42 omega   81.00  177.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -150.0000 96

 43 omega   89.00  163.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   30.0000 74

 44 omega   79.00  171.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 92

 45 omega  122.00  177.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 55

 46 omega   80.00  105.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 25

 47 omega   79.00  117.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 38

 48 omega   80.00  161.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   90.0000 81

 49 omega   90.00  172.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  150.0000 82

 50 omega   80.00  166.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 86

 51 omega   44.00  109.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  120.0000 65

 52 omega   39.00  107.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 68

 53 omega   88.00  114.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -90.0000 26

 54 omega   89.00  136.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -60.0000 47

 55 omega  115.00  142.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 27

 56 omega   45.00   80.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -60.0000 35
;
_diffrn_measurement_device       'four-circle diffractometer'
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_diffrn_orient_matrix_UB_11      -0.1442664000
_diffrn_orient_matrix_UB_12      0.0560342000
_diffrn_orient_matrix_UB_13      -0.0855747000
_diffrn_orient_matrix_UB_21      0.0985613000
_diffrn_orient_matrix_UB_22      0.1268250000
_diffrn_orient_matrix_UB_23      0.0735963000
_diffrn_orient_matrix_UB_31      0.1050544000
_diffrn_orient_matrix_UB_32      0.0291402000
_diffrn_orient_matrix_UB_33      -0.0872798000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.078
_diffrn_reflns_theta_max         67.078
_diffrn_reflns_theta_min         4.067
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.850
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_exptl_absorpt_correction_T_min  0.47172
_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    1.549
_exptl_crystal_description       prism
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         3503
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0418
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0671P)^2^+0.3206P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1123
_refine_ls_wR_factor_ref         0.1204
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2907
_reflns_number_total             3503
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01573_si_002.cif
_cod_data_source_block           201605183
_cod_original_cell_volume        982.95(13)
_cod_database_code               4035644
_chemical_oxdiff_formula         C1H1O1N1S1
_reflns_odcompleteness_completeness 93.42
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
;
_shelx_res_checksum              24091
_shelx_hkl_checksum              24881
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'