Metal-free anomalous [5+1] cycloaddition reactions of donor-acceptor aziridines for the synthesis of 2<i>H</i>-1,4-oxazines.
Zheng, Jianfeng; Bi, Jingzhi; Ma, Lan; Chen, Lvli; Tang, Luhao; Xiong, Dong; Tian, Yin; Chemical communications (Cambridge, England) 59 (2023) 8572–8575; doi:10.1039/d3cc02193a

data_7131845
_publ_section_title
;
 Metal-free anomalous [5+1] cycloaddition reactions of donor-acceptor
 aziridines for the synthesis of 2<i>H</i>-1,4-oxazines.
;
_journal_issue                   55
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              8572
_journal_page_last               8575
_journal_paper_doi               10.1039/d3cc02193a
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C32 H33 N3 O6 S'
_chemical_formula_sum            'C32 H33 N3 O6 S'
_chemical_formula_weight         587.67
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-11-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-11-24 deposited with the CCDC.	2023-06-13 downloaded from the CCDC.
;
_cell_angle_alpha                111.083(6)
_cell_angle_beta                 96.959(5)
_cell_angle_gamma                94.009(5)
_cell_formula_units_Z            2
_cell_length_a                   9.8721(6)
_cell_length_b                   10.9778(7)
_cell_length_c                   15.0003(10)
_cell_measurement_reflns_used    3356
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.0350
_cell_measurement_theta_min      3.3270
_cell_volume                     1494.30(18)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_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      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega    2.00   79.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -       17.6648   57.0000  -60.0000 77

  2 omega    6.00   71.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -       17.6648   57.0000 -120.0000 65

  3 omega    4.00   80.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -       17.6648   57.0000   30.0000 76

  4 omega  -20.00   49.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      -15.4773   57.0000  150.0000 69

  5 omega  -30.00   36.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      -15.4773   57.0000   90.0000 66

  6 omega  -21.00   17.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      -15.4773  -99.0000  120.0000 38
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0450205000
_diffrn_orient_matrix_UB_12      -0.0591747000
_diffrn_orient_matrix_UB_13      -0.0137412000
_diffrn_orient_matrix_UB_21      -0.0165156000
_diffrn_orient_matrix_UB_22      0.0005626000
_diffrn_orient_matrix_UB_23      -0.0471946000
_diffrn_orient_matrix_UB_31      0.0549493000
_diffrn_orient_matrix_UB_32      -0.0369651000
_diffrn_orient_matrix_UB_33      -0.0147376000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12221
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.947
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96820
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_description       block
_exptl_crystal_F_000             620
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     382
_refine_ls_number_reflns         6101
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0462
_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^)+(0.0470P)^2^+0.3162P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1049
_refine_ls_wR_factor_ref         0.1177
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4417
_reflns_number_total             6101
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc02193a2.cif
_cod_data_source_block           211123_s3_lgg
_cod_database_code               7131845
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         c12h12n2o3s1
_shelx_estimated_absorpt_t_max   0.962
_shelx_estimated_absorpt_t_min   0.947
_reflns_odcompleteness_completeness 99.77
_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 Ternary CH refined with riding coordinates:
 C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C22(H22A,H22B), C24(H24A,H24B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20), C27(H27), C28(H28), C30(H30), C31(H31)
2.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C25(H25A,H25B,H25C), C32(H32A,H32B,H32C)
;
_shelx_res_checksum              77599
_olex2_submission_special_instructions 'No special instructions were received'