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_7131846
_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      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2022-06-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-07-01 deposited with the CCDC.	2023-06-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.124(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2530(7)
_cell_length_b                   28.894(2)
_cell_length_c                   13.2728(14)
_cell_measurement_reflns_used    1877
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.0520
_cell_measurement_theta_min      3.3120
_cell_volume                     3024.8(5)
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_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 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -10.00   23.00   0.5000   42.5000
omega____ theta____ kappa____ phi______ frames
    -      -15.3211  -99.0000  -90.0000 66

  2 omega  -45.00   38.00   0.5000   42.5000
omega____ theta____ kappa____ phi______ frames
    -      -15.3211    0.0000  150.0000 166

  3 omega   51.00   81.00   0.5000   42.5000
omega____ theta____ kappa____ phi______ frames
    -       17.5086   57.0000  -30.0000 60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0007669000
_diffrn_orient_matrix_UB_12      0.0193052000
_diffrn_orient_matrix_UB_13      0.0330952000
_diffrn_orient_matrix_UB_21      0.0022286000
_diffrn_orient_matrix_UB_22      -0.0151265000
_diffrn_orient_matrix_UB_23      0.0424137000
_diffrn_orient_matrix_UB_31      0.0898277000
_diffrn_orient_matrix_UB_32      0.0002056000
_diffrn_orient_matrix_UB_33      0.0151209000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0637
_diffrn_reflns_av_unetI/netI     0.0815
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15399
_diffrn_reflns_point_group_measured_fraction_full 0.997
_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         2.966
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.155
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69816
_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    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1240
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     387
_refine_ls_number_reflns         6177
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.1383
_refine_ls_R_factor_gt           0.0789
_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^)+(0.0905P)^2^+0.3272P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1816
_refine_ls_wR_factor_ref         0.2242
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3390
_reflns_number_total             6177
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc02193a2.cif
_cod_data_source_block           220628_s1_lgg_3
_cod_original_cell_volume        3024.7(5)
_cod_database_code               7131846
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         c12h12n2o3
_shelx_estimated_absorpt_t_max   0.962
_shelx_estimated_absorpt_t_min   0.948
_reflns_odcompleteness_completeness 89.69
_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 C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C32) = Uanis(C32A)
3. Others
 Sof(H31C)=Sof(H31D)=Sof(C32A)=Sof(H32D)=Sof(H32E)=Sof(H32F)=1-FVAR(1)
 Sof(H31A)=Sof(H31B)=Sof(C32)=Sof(H32A)=Sof(H32B)=Sof(H32C)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C2(H2)
4.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B), C29(H29A,H29B), C31(H31A,H31B), C31(H31C,H31D)
4.c Aromatic/amide H refined with riding coordinates:
 N3(H3), C9(H9), C10(H10), C11(H11), C12(H12), C14(H14), C16(H16), C17(H17),
 C18(H18), C19(H19), C20(H20), C22(H22), C23(H23), C25(H25), C26(H26)
4.d Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C30(H30A,H30B,H30C), C32(H32A,H32B,H32C), C32A(H32D,H32E,
 H32F)
;
_shelx_res_checksum              82185
_shelx_hkl_checksum              80860
_olex2_submission_special_instructions 'No special instructions were received'