Catalytic Kinetic Resolution of Spiro-Epoxyoxindoles with 1-Naphthols: Switchable Asymmetric Tandem Dearomatization/Oxa-Michael Reaction and Friedel–Crafts Alkylation of 1-Naphthols at the C4 Position
Zhu, Gongming; Li, Yiping; Bao, Guangjun; Sun, Wangsheng; Huang, Liwu; Hong, Liang; Wang, Rui; ACS Catalysis  (2018) 1810–; doi:10.1021/acscatal.7b03268

data_4514378
_publ_section_title
;
 Catalytic Kinetic Resolution of Spiro-Epoxyoxindoles with 1-Naphthols:
 Switchable Asymmetric Tandem Dearomatization/Oxa-Michael Reaction and
 Friedel--Crafts Alkylation of 1-Naphthols at the C4 Position
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              1810
_journal_paper_doi               10.1021/acscatal.7b03268
_journal_year                    2018
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C9 H7 N O2'
_chemical_formula_sum            'C9 H7 N O2'
_chemical_formula_weight         161.16
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_primary     direct
_audit_creation_date             2016-10-11
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.3637
_cell_length_b                   8.4176(1)
_cell_length_c                   20.0620(2)
_cell_measurement_reflns_used    6045
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.9950
_cell_measurement_theta_min      5.6730
_cell_volume                     736.915(11)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.9709
_diffrn_measured_fraction_theta_max 0.9709
_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   -116.00 -18.00   1.00    1.00    --  -41.89 -37.00-150.00   98
  2  \w    -33.00  66.00   1.00    1.00    --   41.89 -37.00 150.00   99
  3  \w      1.00  83.00   1.00    1.00    --   41.89 -99.00  90.00   82
  4  \w     33.00 119.00   1.00    1.00    --  107.79-118.00 -47.00   86
  5  \w     35.00 134.00   1.00    1.00    --  107.79 -45.00 -60.00   99
  6  \w     20.00 178.00   1.00    1.00    --  107.79   0.00-180.00  158
  7  \w     94.00 178.00   1.00    1.00    --  107.79 125.00-120.00   84
  8  \w   -118.00  -9.00   1.00    1.00    --  -41.89 -77.00 120.00  109
  9  \w   -115.00 -14.00   1.00    1.00    --  -41.89 -57.00 -30.00  101
 10  \w     80.00 178.00   1.00    1.00    --  107.79  30.00   0.00   98
 11  \w     36.00 137.00   1.00    1.00    --  107.79 -61.00 120.00  101
 12  \w     75.00 178.00   1.00    1.00    --  107.79  77.00  90.00  103
 13  \w     55.00 178.00   1.00    1.00    --  107.79  15.00 -60.00  123
 14  \w   -115.00 -14.00   1.00    1.00    --  -41.89 -57.00-180.00  101
 15  \w      1.00  83.00   1.00    1.00    --   41.89 -99.00 -30.00   82
 16  \w     79.00 139.00   1.00    1.00    --  107.79  61.00  30.00   60
;
_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      0.0459489000
_diffrn_orient_matrix_UB_12      -0.1806785000
_diffrn_orient_matrix_UB_13      -0.0069507000
_diffrn_orient_matrix_UB_21      -0.0124633000
_diffrn_orient_matrix_UB_22      0.0158517000
_diffrn_orient_matrix_UB_23      -0.0764595000
_diffrn_orient_matrix_UB_31      0.3498141000
_diffrn_orient_matrix_UB_32      0.0243619000
_diffrn_orient_matrix_UB_33      -0.0018391000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0154
_diffrn_reflns_av_unetI/netI     0.0102
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            6981
_diffrn_reflns_theta_full        74.1261
_diffrn_reflns_theta_max         74.13
_diffrn_reflns_theta_min         4.41
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.866
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83678
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.4525
_exptl_crystal_description       block
_exptl_crystal_F_000             337.1849
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.1485
_refine_diff_density_min         -0.1692
_refine_diff_density_rms         0.0356
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.02(16)
_refine_ls_d_res_high            0.8015
_refine_ls_d_res_low             10.0310
_refine_ls_goodness_of_fit_ref   1.0564
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    13
_refine_ls_number_parameters     108
_refine_ls_number_reflns         1470
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0564
_refine_ls_R_factor_all          0.0262
_refine_ls_R_factor_gt           0.0260
_refine_ls_shift/su_max          0.0004
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0396P)^2^+0.1365P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0676
_refine_ls_wR_factor_ref         0.0678
_reflns_Friedel_coverage         0.956
_reflns_limit_h_max              5
_reflns_limit_h_min              -5
_reflns_limit_k_max              10
_reflns_limit_k_min              -10
_reflns_limit_l_max              24
_reflns_limit_l_min              -24
_reflns_number_gt                1458
_reflns_number_total             1470
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            cs7b03268_si_002.cif
_cod_data_source_block           1610094
_cod_original_sg_symbol_Hall     ' P 2ac 2ab'
_cod_database_code               4514378
_chemical_oxdiff_formula         'C20 H20 N4 O4'
_chemical_oxdiff_usercomment     'XJC 20160930'
_reflns_odcompleteness_completeness 99.88
_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, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10a,H10b)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C9(H9), C11(H11), C5(H5), N2(H2)
;
_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 1.224
_oxdiff_exptl_absorpt_empirical_full_min 0.781