[3 + 1]- and [3 + 2]-Cycloadditions of Azaoxyallyl Cations and Sulfur Ylides.
Li, Chao; Jiang, Kun; Ouyang, Qin; Liu, Tian-Yu; Chen, Ying-Chun; Organic letters 18 (2016) 2738–2741; doi:10.1021/acs.orglett.6b01194

data_1555578
_publ_section_title
;
 [3 + 1]- and [3 + 2]-Cycloadditions of Azaoxyallyl Cations and Sulfur
 Ylides.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2738
_journal_page_last               2741
_journal_paper_doi               10.1021/acs.orglett.6b01194
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C23 H19 N O3'
_chemical_formula_sum            'C24 H19 N0.25 O3'
_chemical_formula_weight         358.89
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-03-08
_audit_creation_method
;
Olex2 1.2
(compiled 2014.06.23 svn.r2946 for OlexSys, GUI svn.r4855)
;
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_cell_length_b                   5.9284(4)
_cell_length_c                   14.7885(9)
_cell_measurement_reflns_used    12665
_cell_measurement_temperature    290.56(10)
_cell_measurement_theta_max      25.7120
_cell_measurement_theta_min      3.9710
_cell_volume                     1810.5(2)
_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, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      290.56(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0243
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.927
_diffrn_measurement_details
;
  1 omega  -79.00    9.00   1.0000    6.6700
omega____ theta____ kappa____ phi______ frames
    -       -9.4283  -38.0000   60.0000 88

  2 omega  -20.00   30.00   1.0000    6.6700
omega____ theta____ kappa____ phi______ frames
    -       -9.4283  -99.0000  -30.0000 50

  3 omega  -20.00   50.00   1.0000    6.6700
omega____ theta____ kappa____ phi______ frames
    -       11.0689  -99.0000  120.0000 70

  4 omega   -6.00   78.00   1.0000    6.6700
omega____ theta____ kappa____ phi______ frames
    -       11.0689   57.0000  -30.0000 84

  5 omega  -18.00   82.00   1.0000    6.6700
omega____ theta____ kappa____ phi______ frames
    -       11.0689   19.0000  -90.0000 100

  6 omega  -20.00   50.00   1.0000    6.6700
omega____ theta____ kappa____ phi______ frames
    -       11.0689  -99.0000  -30.0000 70

  7 omega  -56.00   28.00   1.0000    6.6700
omega____ theta____ kappa____ phi______ frames
    -       11.0689  -57.0000  150.0000 84

  8 omega  -20.00   50.00   1.0000    6.6700
omega____ theta____ kappa____ phi______ frames
    -       11.0689  -99.0000   90.0000 70

  9 omega  -20.00   50.00   1.0000    6.6700
omega____ theta____ kappa____ phi______ frames
    -       11.0689  -99.0000 -120.0000 70

 10 omega  -56.00   28.00   1.0000    6.6700
omega____ theta____ kappa____ phi______ frames
    -       11.0689  -57.0000 -150.0000 84

 11 omega   -6.00   68.00   1.0000    6.6700
omega____ theta____ kappa____ phi______ frames
    -       11.0689   57.0000  150.0000 74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0282164000
_diffrn_orient_matrix_UB_12      -0.0552441000
_diffrn_orient_matrix_UB_13      0.0159247000
_diffrn_orient_matrix_UB_21      -0.0157040000
_diffrn_orient_matrix_UB_22      0.0231036000
_diffrn_orient_matrix_UB_23      -0.0416383000
_diffrn_orient_matrix_UB_31      0.0115424000
_diffrn_orient_matrix_UB_32      -0.1037350000
_diffrn_orient_matrix_UB_33      -0.0177457000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.927
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            27056
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.893
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.082
_diffrn_reflns_theta_min         3.437
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41096
_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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
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_exptl_crystal_density_diffrn    1.317
_exptl_crystal_description       block
_exptl_crystal_F_000             755
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 1406 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3577
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0375
_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^)+(0.0465P)^2^+0.1053P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0824
_refine_ls_wR_factor_ref         0.0843
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_reflns_Friedel_fraction_full    0.980
_reflns_Friedel_fraction_max     0.857
_reflns_number_gt                3307
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_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b01194_si_003.cif
_cod_data_source_block           5a
_cod_original_cell_volume        1810.56(19)
_cod_database_code               1555578
_shelxl_version_number           2014-1
_chemical_oxdiff_formula         'C1 H1 O1 N1'
_reflns_odcompleteness_completeness 99.36
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     23.21
_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 O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C4(H4), C2(H2), C17(H17), C6(H6), C16(H16), C21(H21), C5(H5), C3(H3),
 C24(H24), C15(H15), C22(H22), C25(H25), C13(H13), C14(H14), C23(H23)
2.c Idealised tetrahedral OH refined as rotating group:
 O27(H27)
;
_shelx_res_checksum              14364
_shelx_hkl_checksum              81911
_olex2_date_sample_data_collection 1442627140.06
_olex2_submission_special_instructions 'No special instructions were received'