Construction of spirocyclic oxindole derivatives by copper-catalyzed enantioselective Michael/hemiketalization in aqueous media.
Li, Ning; Lu, Wenjing; Gu, Weizhi; Li, Kuiliang; Li, Jindong; Lu, Yangmian; Zha, Zhenggen; Wang, Zhiyong; Chemical communications (Cambridge, England) 58 (2022) 10957–10960; doi:10.1039/d2cc04370j

data_7130626
_publ_section_title
;
 Construction of spirocyclic oxindole derivatives by copper-catalyzed
 enantioselective Michael/hemiketalization in aqueous media.
;
_journal_issue                   78
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              10957
_journal_page_last               10960
_journal_paper_doi               10.1039/d2cc04370j
_journal_volume                  58
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C29 H23 N O7'
_chemical_formula_sum            'C29 H23 N O7'
_chemical_formula_weight         497.48
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-03-04
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6403)
;
_audit_update_record
;
2022-05-06 deposited with the CCDC.	2022-08-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.7964(2)
_cell_length_b                   12.7829(2)
_cell_length_c                   16.2814(3)
_cell_measurement_reflns_used    8442
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.9040
_cell_measurement_theta_min      4.3950
_cell_volume                     2455.11(7)
_computing_cell_refinement       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/4 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2169
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_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   -115.00 -16.00   1.00    7.00    --  -40.26 -38.00   0.00   99
  2  \w    -34.00  65.00   1.00    7.00    --   40.26 -38.00 120.00   99
  3  \w      6.00  81.00   1.00    7.00    --   40.26 -99.00 -90.00   75
  4  \w     23.00 107.00   1.00   14.00    --  106.05 -94.00  90.00   84
  5  \w    103.00 178.00   1.00   14.00    --  106.05  77.00 150.00   75
  6  \w     97.00 178.00   1.00   14.00    --  106.05 125.00 150.00   81
  7  \w     23.00 107.00   1.00   14.00    --  106.05 -94.00 150.00   84
  8  \w    103.00 178.00   1.00   14.00    --  106.05  77.00-180.00   75
  9  \w    103.00 178.00   1.00   14.00    --  106.05  77.00 -60.00   75
 10  \w     30.00 134.00   1.00   14.00    --  106.05 -30.00   0.00  104
 11  \w   -113.00 -63.00   1.00    7.00    --  -40.26-147.00 -66.00   50
 12  \w   -112.00 -12.00   1.00    7.00    --  -40.26 -57.00 150.00  100
 13  \w   -112.00 -12.00   1.00    7.00    --  -40.26 -57.00 -90.00  100
 14  \w     23.00  52.00   1.00   14.00    --  106.05 -94.00 -90.00   29
 15  \w    103.00 178.00   1.00   14.00    --  106.05  77.00   0.00   75
 16  \w     80.00 178.00   1.00   14.00    --  106.05  45.00  90.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0079422000
_diffrn_orient_matrix_UB_12      0.0886734000
_diffrn_orient_matrix_UB_13      -0.0638620000
_diffrn_orient_matrix_UB_21      -0.0079204000
_diffrn_orient_matrix_UB_22      -0.0809662000
_diffrn_orient_matrix_UB_23      -0.0698903000
_diffrn_orient_matrix_UB_31      -0.1300404000
_diffrn_orient_matrix_UB_32      0.0102957000
_diffrn_orient_matrix_UB_33      0.0003474000
_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  0.0343
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            18417
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.964
_diffrn_reflns_theta_min         4.397
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.802
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75686
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.110a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 1563 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.01(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         4814
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0450
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0587P)^2^+0.3905P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1112
_refine_ls_wR_factor_ref         0.1194
_reflns_Friedel_coverage         0.758
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.972
_reflns_number_gt                4092
_reflns_number_total             4814
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc04370j2.cif
_cod_data_source_block           ln221_auto
_cod_depositor_comments          'Adding full bibliography for 7130626.cif.'
_cod_database_code               7130626
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         c20h20n2o2
_shelx_estimated_absorpt_t_max   0.889
_shelx_estimated_absorpt_t_min   0.856
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C20(H20A,H20B), C28(H28A,H28B)
1.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C5(H5), C16(H16), C18(H18), C17(H17), C26(H26), C2(H2), C4(H4),
 C25(H25), C3(H3A), C22(H22), C23(H23), C24(H24)
1.c Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C)
1.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_res_checksum              83707
_shelx_hkl_checksum              25056
_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 1.395
_oxdiff_exptl_absorpt_empirical_full_min 0.572