Copper(i)/Ganphos catalysis: enantioselective synthesis of diverse spirooxindoles using iminoesters and alkyl substituted methyleneindolinones.
Cui, Hao; Li, Ke; Wang, Yue; Song, Manman; Wang, Congcong; Wei, Donghui; Li, Er-Qing; Duan, Zheng; Mathey, François; Organic & biomolecular chemistry 18 (2020) 3740–3746; doi:10.1039/d0ob00546k

data_7157484
_publ_section_title
;
 Copper(i)/Ganphos catalysis: enantioselective synthesis of diverse
 spirooxindoles using iminoesters and alkyl substituted
 methyleneindolinones.
;
_journal_issue                   19
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3740
_journal_page_last               3746
_journal_paper_doi               10.1039/d0ob00546k
_journal_volume                  18
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H23 Cl N2 O3'
_chemical_formula_sum            'C22 H23 Cl N2 O3'
_chemical_formula_weight         398.87
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_block_doi                 10.5517/ccdc.csd.cc23mtn7
_audit_creation_date             2019-09-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-09-24 deposited with the CCDC.	2020-04-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 119.944(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   24.1998(14)
_cell_length_b                   12.3700(6)
_cell_length_c                   9.5879(6)
_cell_measurement_reflns_used    6811
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.0840
_cell_measurement_theta_min      4.1430
_cell_volume                     2487.0(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -62.00 -37.00   1.00    1.50    --  -33.50 178.00 120.00   25
  2  \w    -47.00  -7.00   1.00    1.50    --  -33.50 -77.00   0.00   40
  3  \w    -85.00 -48.00   1.00    1.50    --  -33.50 -77.00 -30.00   37
  4  \w    -61.00 -36.00   1.00    1.50    --  -33.50 178.00-180.00   25
  5  \w   -105.00 -80.00   1.00    1.50    --  -33.50 178.00-180.00   25
  6  \w     14.00 107.00   1.00    1.50    --   36.47  37.00-150.00   93
  7  \w     74.00 100.00   1.00    1.50    --   36.47 178.00 -90.00   26
  8  \w     51.00 106.00   1.00    1.50    --   36.47  37.00 120.00   55
  9  \w     57.00 104.00   1.00    1.50    --   36.47 178.00   0.00   47
 10  \w     68.00 102.00   1.00    1.50    --   36.47 178.00 120.00   34
 11  \w     62.00 110.00   1.00    1.50    --   36.47 178.00  60.00   48
 12  \w     61.00  96.00   1.00    7.50    --  108.00-111.00 120.00   35
 13  \w     38.00 110.00   1.00    7.50    --  108.00 -94.00  30.00   72
 14  \w     42.00 137.00   1.00    7.50    --  108.00 -77.00-180.00   95
 15  \w     39.00 127.00   1.00    7.50    --  108.00 -30.00  60.00   88
 16  \w     88.00 177.00   1.00    6.00    --  108.00  30.00-120.00   89
 17  \w    152.00 177.00   1.00    6.00    --  108.00  45.00-120.00   25
 18  \w    109.00 135.00   1.00    6.00    --  108.00 111.00  60.00   26
 19  \w     39.00  90.00   1.00    6.00    --  108.00 -77.00 120.00   51
 20  \w     27.00  56.00   1.00    1.00    --   36.47  24.00 -78.00   29
 21  \w    -15.00  19.00   1.00    1.00    --    0.00 -57.00   0.00   34
 22  \w      7.00  32.00   1.00    1.00    --   36.47  19.00 120.00   25
 23  \w     54.00  80.00   1.00    1.00    --   36.47  57.00  30.00   26
 24  \w     41.00  67.00   1.00    1.00    --   36.47  37.00 120.00   26
 25  \w     57.00  82.00   1.00    1.00    --   36.47 178.00 150.00   25
 26  \w     69.00 105.00   1.00    1.00    --   36.47  57.00   0.00   36
 27  \w     76.00 105.00   1.00    1.00    --   36.47  77.00 120.00   29
 28  \w      0.00  31.00   1.00    1.00    --   36.47  91.00  -2.60   31
 29  \w     66.00  92.00   1.00    1.00    --   36.47  19.00 120.00   26
 30  \w     35.00  61.00   1.00    1.00    --   36.47  57.00 150.00   26
 31  \w     32.00  63.00   1.00    1.00    --   36.47  77.00  60.00   31
 32  \w     42.00 100.00   1.00    1.00    --   36.47  77.00  30.00   58
 33  \w     -9.00  16.00   1.00    1.00    --   36.47 108.00  58.07   25
 34  \w     35.00  61.00   1.00    1.00    --   36.47  57.00   0.00   26
 35  \w      9.00  34.00   1.00    1.00    --   36.47  77.00  30.00   25
 36  \w     24.00  50.00   1.00    1.00    --   36.47  57.00 120.00   26
 37  \w     84.00 110.00   1.00    1.00    --   36.47 178.00  90.00   26
 38  \w     14.00  40.00   1.00    1.00    --   36.47  77.00 120.00   26
 39  \w     45.00  71.00   1.00    1.00    --   36.47  57.00 -30.00   26
 40  \w     19.00  44.00   1.00    1.00    --   36.47  57.00-180.00   25
 41  \w     58.00  84.00   1.00    1.00    --   36.47 178.00-120.00   26
 42  \w    130.00 156.00   1.00    6.00    --  108.00  30.00 120.00   26
 43  \w     87.00 143.00   1.00    6.00    --  108.00  30.00  60.00   56
 44  \w     88.00 114.00   1.00    6.00    --  108.00  61.00   0.00   26
 45  \w     88.00 114.00   1.00    6.00    --  108.00  61.00 -30.00   26
 46  \w     79.00 104.00   1.00    6.00    --  108.00  77.00 -60.00   25
 47  \w     83.00 109.00   1.00    6.00    --  108.00  77.00  90.00   26
 48  \w     86.00 112.00   1.00    6.00    --  108.00  30.00 120.00   26
 49  \w     89.00 115.00   1.00    6.00    --  108.00  61.00  60.00   26
 50  \w     79.00 104.00   1.00    6.00    --  108.00  77.00  60.00   25
 51  \w    153.00 178.00   1.00    6.00    --  108.00  30.00 -30.00   25
 52  \w     79.00 104.00   1.00    6.00    --  108.00  77.00   0.00   25
 53  \w     88.00 114.00   1.00    6.00    --  108.00  45.00  90.00   26
 54  \w     88.00 118.00   1.00    6.00    --  108.00  61.00  30.00   30
 55  \w     81.00 106.00   1.00    6.00    --  108.00  74.00  28.64   25
 56  \w     88.00 114.00   1.00    6.00    --  108.00  61.00  90.00   26
 57  \w    129.00 155.00   1.00    6.00    --  108.00  77.00 -30.00   26
 58  \w     82.00 133.00   1.00    6.00    --  108.00  30.00  30.00   51
 59  \w     79.00 104.00   1.00    6.00    --  108.00  77.00 -30.00   25
 60  \w     84.00 123.00   1.00    6.00    --  108.00  30.00   0.00   39
 61  \w     88.00 124.00   1.00    6.00    --  108.00  45.00   0.00   36
 62  \w     87.00 117.00   1.00    6.00    --  108.00  42.00  -9.89   30
 63  \w     88.00 114.00   1.00    6.00    --  108.00  61.00 -60.00   26
 64  \w     79.00 105.00   1.00    6.00    --  108.00  77.00  30.00   26
 65  \w     89.00 137.00   1.00    6.00    --  108.00  45.00 -30.00   48
 66  \w     89.00 132.00   1.00    6.00    --  108.00  45.00  30.00   43
 67  \w     79.00 105.00   1.00    6.00    --  108.00  77.00   5.88   26
 68  \w     83.00 129.00   1.00    6.00    --  108.00  30.00 -30.00   46
 69  \w     83.00 129.00   1.00    6.00    --  108.00  30.00  90.00   46
 70  \w     24.00  50.00   1.00    1.00    --   36.47  57.00 120.00   26
 71  \w     51.00  77.00   1.00    1.00    --   36.47  57.00   0.00   26
 72  \w     41.00  67.00   1.00    1.00    --   36.47  37.00 120.00   26
 73  \w     69.00  95.00   1.00    1.00    --   36.47  57.00  30.00   26
 74  \w     24.00  50.00   1.00    1.00    --   36.47  57.00-180.00   26
 75  \w     84.00 110.00   1.00    6.00    --  108.00  30.00   0.00   26
 76  \w     89.00 115.00   1.00    6.00    --  108.00  45.00 -30.00   26
 77  \w     91.00 117.00   1.00    6.00    --  108.00  61.00  60.00   26
 78  \w     87.00 113.00   1.00    6.00    --  108.00  42.00 110.61   26
 79  \w     85.00 111.00   1.00    6.00    --  108.00  37.00 115.89   26
 80  \w     69.00  95.00   1.00    1.00    --   36.47  57.00  30.00   26
 81  \w     41.00  67.00   1.00    1.00    --   36.47  37.00 120.00   26
 82  \w     24.00  50.00   1.00    1.00    --   36.47  57.00-180.00   26
 83  \w     51.00  77.00   1.00    1.00    --   36.47  57.00   0.00   26
 84  \w     24.00  50.00   1.00    1.00    --   36.47  57.00 120.00   26
 85  \w     91.00 117.00   1.00    6.00    --  108.00  61.00  60.00   26
 86  \w     89.00 115.00   1.00    6.00    --  108.00  45.00 -30.00   26
 87  \w     84.00 110.00   1.00    6.00    --  108.00  30.00   0.00   26
 88  \w     24.00  50.00   1.00    1.00    --   36.47  57.00 120.00   26
 89  \w     69.00  95.00   1.00    1.00    --   36.47  57.00  30.00   26
 90  \w     24.00  50.00   1.00    1.00    --   36.47  57.00-180.00   26
 91  \w     41.00  67.00   1.00    1.00    --   36.47  37.00 120.00   26
 92  \w     51.00  77.00   1.00    1.00    --   36.47  57.00   0.00   26
 93  \w     84.00 110.00   1.00    6.00    --  108.00  30.00   0.00   26
 94  \w     89.00 115.00   1.00    6.00    --  108.00  45.00 -30.00   26
 95  \w     91.00 117.00   1.00    6.00    --  108.00  61.00  60.00   26
 96  \w     86.00 112.00   1.00    6.00    --  108.00  39.00  82.69   26
 97  \w     69.00  95.00   1.00    1.00    --   36.47  57.00  30.00   26
 98  \w     41.00  67.00   1.00    1.00    --   36.47  37.00 120.00   26
 99  \w     24.00  50.00   1.00    1.00    --   36.47  57.00-180.00   26
100  \w     51.00  77.00   1.00    1.00    --   36.47  57.00   0.00   26
101  \w     24.00  50.00   1.00    1.00    --   36.47  57.00 120.00   26
102  \w     91.00 117.00   1.00    6.00    --  108.00  61.00  60.00   26
103  \w     89.00 115.00   1.00    6.00    --  108.00  45.00 -30.00   26
104  \w     84.00 110.00   1.00    6.00    --  108.00  30.00   0.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0401215000
_diffrn_orient_matrix_UB_12      0.0387657000
_diffrn_orient_matrix_UB_13      -0.1755796000
_diffrn_orient_matrix_UB_21      -0.0589977000
_diffrn_orient_matrix_UB_22      0.0085798000
_diffrn_orient_matrix_UB_23      0.0207410000
_diffrn_orient_matrix_UB_31      0.0174342000
_diffrn_orient_matrix_UB_32      0.1180243000
_diffrn_orient_matrix_UB_33      0.0561157000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            17070
_diffrn_reflns_point_group_measured_fraction_full 0.924
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_theta_full        67.063
_diffrn_reflns_theta_max         67.063
_diffrn_reflns_theta_min         4.217
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.526
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83221
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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    1.065
_exptl_crystal_description       prism
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 1510 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.000(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4120
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0448
_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^)+(0.0880P)^2^+0.1735P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1259
_refine_ls_wR_factor_ref         0.1291
_reflns_Friedel_coverage         0.761
_reflns_Friedel_fraction_full    0.842
_reflns_Friedel_fraction_max     0.842
_reflns_number_gt                3851
_reflns_number_total             4120
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob00546k2.cif
_cod_data_source_block           201909229
_cod_depositor_comments          'Adding full bibliography for 7157484.cif.'
_cod_database_code               7157484
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C20H20O4Cl1
_shelx_estimated_absorpt_t_max   0.875
_shelx_estimated_absorpt_t_min   0.781
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N2-H2
 0.87 with sigma of 0.02
 N1-H1A
 0.87 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C7(H7), C16(H16), C17(H17), C18(H18)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C5(H5), C12(H12), C13(H13), C14(H14), C15(H15)
3.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C22(H22A,H22B,H22C)
;
_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 1.321
_oxdiff_exptl_absorpt_empirical_full_min 0.882