Facile synthesis of novel spiroheterocycles via diastereoselective aziridination of cyclic enones
Yang, Kai-Chuan; Li, Jun-Long; Shen, Xu-Dong; Li, Qiang; Leng, Hai-Jun; Huang, Qian; Zheng, Peng-Kun; Gou, Xiao-Jun; Zhi, Yong-Gang; RSC Adv. 7 (2017) 21175–; doi:10.1039/C6RA28508B

data_7228084
_publ_section_title
;
 Facile synthesis of novel spiroheterocycles via diastereoselective
 aziridination of cyclic enones
;
_journal_issue                   34
_journal_name_full               'RSC Adv.'
_journal_page_first              21175
_journal_paper_doi               10.1039/C6RA28508B
_journal_volume                  7
_journal_year                    2017
_chemical_formula_moiety         'C27 H29 Br N2 O5'
_chemical_formula_sum            'C27 H29 Br N2 O5'
_chemical_formula_weight         541.43
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-05-10
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-05-11 deposited with the CCDC.
2017-03-27 downloaded from the CCDC.
;
_cell_angle_alpha                99.051(4)
_cell_angle_beta                 106.017(3)
_cell_angle_gamma                106.133(4)
_cell_formula_units_Z            2
_cell_length_a                   9.8013(3)
_cell_length_b                   11.1877(5)
_cell_length_c                   13.1188(6)
_cell_measurement_reflns_used    7518
_cell_measurement_temperature    150(40)
_cell_measurement_theta_max      72.6030
_cell_measurement_theta_min      4.8310
_cell_volume                     1284.88(10)
_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_environment      N~2~
_diffrn_ambient_temperature      150(40)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega   18.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171   38.0000  120.0000 88

  2 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -57.0000  120.0000 84

  3 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -99.0000   60.0000 74

  4 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171 -125.0000 -120.0000 67

  5 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -57.0000 -120.0000 84

  6 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -99.0000   30.0000 74

  7 omega  -33.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171    0.0000 -120.0000 139

  8 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -99.0000    0.0000 74

  9 omega   39.00  109.00   1.0000    3.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 70

 10 omega   91.00  176.00   1.0000    3.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -180.0000 85

 11 omega   38.00   91.00   1.0000    3.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 53

 12 omega   40.00   98.00   1.0000    3.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 58

 13 omega   40.00   98.00   1.0000    3.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   60.0000 58

 14 omega   39.00  109.00   1.0000    3.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   90.0000 70

 15 omega   91.00  176.00   1.0000    3.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -60.0000 85

 16 omega   39.00  109.00   1.0000    3.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000    0.0000 70

 17 omega   38.00   91.00   1.0000    3.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 53

 18 omega   38.00  116.00   1.0000    3.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -30.0000 78

 19 omega   38.00   91.00   1.0000    3.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 53

 20 omega   39.00  109.00   1.0000    3.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 70

 21 omega   70.00  178.00   1.0000    3.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  120.0000 108

 22 omega   40.00   98.00   1.0000    3.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  120.0000 58

 23 omega   38.00   91.00   1.0000    3.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 53

 24 omega   40.00   98.00   1.0000    3.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 58

 25 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171   57.0000  -90.0000 84

 26 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171   57.0000 -150.0000 84

 27 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171   77.0000    0.0000 94

 28 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171   77.0000  -30.0000 94

 29 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171   77.0000   90.0000 94

 30 omega    0.00   26.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171   94.0000  151.0190 26

 31 omega   87.00  178.00   1.0000    3.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000    0.0000 91

 32 omega   87.00  155.00   1.0000    3.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000 -120.0000 68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0527922000
_diffrn_orient_matrix_UB_12      -0.0111983000
_diffrn_orient_matrix_UB_13      -0.1242153000
_diffrn_orient_matrix_UB_21      -0.0382428000
_diffrn_orient_matrix_UB_22      -0.1469389000
_diffrn_orient_matrix_UB_23      -0.0228338000
_diffrn_orient_matrix_UB_31      -0.1610946000
_diffrn_orient_matrix_UB_32      -0.0155531000
_diffrn_orient_matrix_UB_33      0.0002218000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13582
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.072
_diffrn_reflns_theta_max         67.072
_diffrn_reflns_theta_min         4.253
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.508
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55391
_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
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_description       needle
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.996
_refine_diff_density_min         -0.464
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         4589
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0504
_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^)+(0.0947P)^2^+0.4225P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1316
_refine_ls_wR_factor_ref         0.1341
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4327
_reflns_number_total             4589
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ra28508b2.cif
_cod_data_source_block           yxq-ykc-dj
_cod_database_code               7228084
_reflns_odcompleteness_completeness 99.98
_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:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00E(H00E), C17(H17), C3(H3), C2(H2), C10(H10), C14(H14),
 C11(H11), C13(H13), C12(H12)
2.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C23(H23A,H23B,H23C), C20(H20A,H20B,
 H20C)
;
_shelx_res_checksum              55439
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-05-10
_olex2_submission_special_instructions 'No special instructions were received'