AgOTf-Catalyzed Sequential Synthesis of 4-Isoquinolone via Oxidative Ring Opening of Aziridines and Aza-Michael Addition
xing, siyang; Cui, Hong; Gu, Nan; Li, Ying; Wang, Kui; Tian, Dawei; Qin, Jiajing; Liu, Qiaoyang; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB02167D

data_7155874
_publ_section_title
;
 AgOTf-Catalyzed Sequential Synthesis of 4-Isoquinolone via Oxidative Ring
 Opening of Aziridines and Aza-Michael Addition
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB02167D
_journal_year                    2017
_chemical_formula_moiety         'C21 H21 N O7 S'
_chemical_formula_sum            'C21 H21 N O7 S'
_chemical_formula_weight         431.45
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-06-13
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2017-06-13 deposited with the CCDC.
2017-09-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.6868(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.18906(12)
_cell_length_b                   11.13074(16)
_cell_length_c                   20.4649(3)
_cell_measurement_reflns_used    10378
_cell_measurement_temperature    135.00(10)
_cell_measurement_theta_max      73.8580
_cell_measurement_theta_min      4.0100
_cell_volume                     2074.36(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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      135.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2740
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     35.00 125.00   1.00    1.00    --  107.08 -61.00  60.00   90
  2  \w     81.00 175.00   1.00    1.00    --  107.08  45.00 120.00   94
  3  \w    125.00 154.00   1.00    1.00    --  107.08  61.00  90.00   29
  4  \w     81.00 160.00   1.00    1.00    --  107.08  45.00 150.00   79
  5  \w     78.00 103.00   1.00    1.00    --  107.08  61.00 150.00   25
  6  \w     78.00 104.00   1.00    1.00    --  107.08  61.00 120.00   26
  7  \w     78.00 105.00   1.00    1.00    --  107.08  61.00  90.00   27
  8  \w     74.00 100.00   1.00    1.00    --  107.08  77.00 120.00   26
  9  \w     74.00 100.00   1.00    1.00    --  107.08  77.00 150.00   26
 10  \w     74.00 100.00   1.00    1.00    --  107.08  77.00  90.00   26
 11  \w     38.00  64.00   1.00    1.00    --   41.49  38.00 120.00   26
 12  \w     19.00  83.00   1.00    1.00    --   41.49  57.00 150.00   64
 13  \w     22.00  78.00   1.00    1.00    --   41.49  38.00 150.00   56
 14  \w     12.00  38.00   1.00    1.00    --   41.49  77.00  90.00   26
 15  \w     35.00 135.00   1.00    1.00    --  107.08 -61.00 -90.00  100
 16  \w     82.00 177.00   1.00    1.00    --  107.08  45.00-120.00   95
 17  \w    141.00 167.00   1.00    1.00    --  107.08  61.00-150.00   26
 18  \w     84.00 170.00   1.00    1.00    --  107.08  45.00-180.00   86
 19  \w     79.00 104.00   1.00    1.00    --  107.08  61.00-150.00   25
 20  \w     82.00 108.00   1.00    1.00    --  107.08  45.00-150.00   26
 21  \w     82.00 109.00   1.00    1.00    --  107.08  61.00-120.00   27
 22  \w     74.00 100.00   1.00    1.00    --  107.08  77.00-150.00   26
 23  \w     78.00 104.00   1.00    1.00    --  107.08  61.00-180.00   26
 24  \w     74.00 100.00   1.00    1.00    --  107.08  77.00-180.00   26
 25  \w     58.00  95.00   1.00    1.00    --   41.49  57.00-180.00   37
 26  \w     25.00  51.00   1.00    1.00    --   41.49  57.00-180.00   26
 27  \w      9.00 105.00   1.00    1.00    --   41.49  77.00-150.00   96
 28  \w     58.00 101.00   1.00    1.00    --  107.08 -95.00-180.00   43
 29  \w      4.00  61.00   1.00    1.00    --   41.49 -99.00  60.00   57
 30  \w     28.00  82.00   1.00    1.00    --  107.08 -95.00  60.00   54
 31  \w    -92.00  -2.00   1.00    1.00    --  -41.49 125.00-120.00   90
 32  \w    -97.00 -62.00   1.00    1.00    --  -41.49-146.00-118.00   35
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1609113000
_diffrn_orient_matrix_UB_12      -0.0354585000
_diffrn_orient_matrix_UB_13      0.0032032000
_diffrn_orient_matrix_UB_21      0.0261367000
_diffrn_orient_matrix_UB_22      0.0115195000
_diffrn_orient_matrix_UB_23      0.0756945000
_diffrn_orient_matrix_UB_31      -0.0450885000
_diffrn_orient_matrix_UB_32      0.1332919000
_diffrn_orient_matrix_UB_33      -0.0056646000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0246
_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       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            17531
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.075
_diffrn_reflns_theta_max         67.075
_diffrn_reflns_theta_min         4.360
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.769
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32843
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
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    1.382
_exptl_crystal_description       block
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         1.303
_refine_diff_density_min         -0.552
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         3706
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.226
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0558
_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^)+(0.0856P)^2^+2.3149P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1546
_refine_ls_wR_factor_ref         0.1581
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3390
_reflns_number_total             3706
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob02167d2.cif
_cod_data_source_block           a160907a
_cod_database_code               7155874
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.97
_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. Uiso/Uaniso restraints and constraints
Uanis(C16) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.002
Uanis(O7) \\sim Ueq, Uanis(O6) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.002
3.a Ternary CH refined with riding coordinates:
 C5(H5), C17(H17)
3.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
3.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C11(H11), C12(H12), C14(H14), C15(H15)
3.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C19(H19A,H19B,H19C), C21(H21A,H21B,H21C)
;
_olex2_date_sample_data_collection 2016-09-07
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.880
_oxdiff_exptl_absorpt_empirical_full_min 0.535