Enantioselective synthesis of indanone spiro-isochromanone derivatives via a dinuclear zinc-catalyzed Michael/transesterification tandem reaction.
Yang, Xiao-Chao; Xu, Meng; Wang, Jin-Bao; Liu, Meng-Meng; Mathey, François; Hua, Yuan-Zhao; Wang, Min-Can; Organic & biomolecular chemistry 18 (2020) 3917–3926; doi:10.1039/d0ob00541j

data_7157492
_publ_section_title
;
 Enantioselective synthesis of indanone spiro-isochromanone derivatives
 via a dinuclear zinc-catalyzed Michael/transesterification tandem
 reaction.
;
_journal_issue                   20
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3917
_journal_page_last               3926
_journal_paper_doi               10.1039/d0ob00541j
_journal_volume                  18
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25 H17 Cl O4'
_chemical_formula_sum            'C25 H17 Cl O4'
_chemical_formula_weight         416.83
_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   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2019-01-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-06-10 deposited with the CCDC.	2020-05-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.832(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.9619(4)
_cell_length_b                   9.8922(2)
_cell_length_c                   22.6104(5)
_cell_measurement_reflns_used    8045
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.9200
_cell_measurement_theta_min      4.9400
_cell_volume                     3988.95(15)
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_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
;
  1 omega   42.00   68.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000    0.0000 -150.0000 26

  2 omega  -99.00  -55.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000  -60.0000 44

  3 omega  -31.00    2.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000  120.0000 33

  4 omega   -3.00   41.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  -90.0000 44

  5 omega   25.00   63.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000  120.0000 38

  6 omega   58.00  109.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -150.0000 51

  7 omega   43.00   84.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000  -60.0000 41

  8 omega   72.00  104.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   90.0000 32

  9 omega   59.00  103.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  120.0000 44

 10 omega  -34.00   10.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -19.0000  -90.0000 44

 11 omega   57.00   93.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   60.0000 36

 12 omega   43.00   85.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000   60.0000 42

 13 omega   -3.00   77.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000 -120.0000 80

 14 omega  145.00  178.00   1.0000    9.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  150.0000 33

 15 omega   66.00  125.00   1.0000    9.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  150.0000 59

 16 omega   87.00  133.00   1.0000    9.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   90.0000 46

 17 omega   45.00   80.00   1.0000    9.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   90.0000 35

 18 omega   50.00   91.00   1.0000    9.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 41

 19 omega   48.00   74.00   1.0000    9.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 26

 20 omega   44.00   97.00   1.0000    9.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -90.0000 53

 21 omega   52.00  119.00   1.0000    9.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  -30.0000 67

 22 omega  100.00  147.00   1.0000    9.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  150.0000 47

 23 omega   48.00   75.00   1.0000    9.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 27

 24 omega   37.00   62.00   1.0000    9.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 25

 25 omega   88.00  177.00   1.0000    9.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 89

 26 omega  -82.00  -56.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000    0.0000 26

 27 omega  -64.00  -34.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000 -150.0000 30

 28 omega   72.00  102.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000  -30.0000 30

 29 omega   77.00  103.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   30.0000 26

 30 omega   30.00   56.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000 -150.0000 26

 31 omega    0.00   26.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000    0.0000 26

 32 omega   18.00   50.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000  -30.0000 32

 33 omega   16.00   62.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000 -120.0000 46

 34 omega   11.00   37.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   76.0000   87.0000 26

 35 omega   21.00   55.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000   60.0000 34

 36 omega    7.00  103.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   19.0000  -90.0000 96

 37 omega   43.00   94.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   76.0000   87.0000 51

 38 omega   83.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   60.0000 26

 39 omega   -8.00   18.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  107.0000  174.0795 26

 40 omega   56.00   82.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 26

 41 omega   79.00  106.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 27

 42 omega   82.00  108.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000 -150.0000 26

 43 omega   72.00  105.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -112.0000   74.0000 33

 44 omega   52.00   99.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -30.0000 47

 45 omega   90.00  116.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -150.0000 26

 46 omega  114.00  149.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   90.0000 35

 47 omega   42.00   68.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 26

 48 omega   64.00   99.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000 -150.0000 35

 49 omega  118.00  175.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -150.0000 57

 50 omega   79.00  104.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 25

 51 omega  138.00  164.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 26

 52 omega   84.00  129.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000 -120.0000 45

 53 omega   54.00  112.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -60.0000 58

 54 omega   80.00  132.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0394166000
_diffrn_orient_matrix_UB_12      -0.1186777000
_diffrn_orient_matrix_UB_13      -0.0350594000
_diffrn_orient_matrix_UB_21      -0.0287807000
_diffrn_orient_matrix_UB_22      -0.0517832000
_diffrn_orient_matrix_UB_23      0.0573675000
_diffrn_orient_matrix_UB_31      -0.0712595000
_diffrn_orient_matrix_UB_32      0.0866098000
_diffrn_orient_matrix_UB_33      -0.0137012000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            17206
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.075
_diffrn_reflns_theta_max         67.075
_diffrn_reflns_theta_min         4.960
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.948
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.26821
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_description       prism
_exptl_crystal_F_000             1728
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 2793 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.007(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     541
_refine_ls_number_reflns         7132
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0392
_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^)+(0.0652P)^2^+0.6251P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1099
_reflns_Friedel_coverage         0.880
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                6622
_reflns_number_total             7132
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob00541j2.cif
_cod_data_source_block           20190118
_cod_depositor_comments          'Adding full bibliography for 7157492.cif.'
_cod_original_cell_volume        3988.97(15)
_cod_database_code               7157492
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C28H31ON6Cl1
_shelx_estimated_absorpt_t_max   0.829
_shelx_estimated_absorpt_t_min   0.733
_reflns_odcompleteness_completeness 99.95
_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
2.a Ternary CH refined with riding coordinates:
 C17(H17), C17'(H17')
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C18(H18C,H18D), C3'(H3'A,H3'B), C18'(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14), C15(H15),
 C21(H21), C22(H22), C24(H24), C25(H25), C6'(H6'), C7'(H7'), C8'(H8'), C9'(H9'),
  C12'(H12'), C13'(H13'), C14'(H14'), C15'(H15'), C21'(H21'), C22'(H22'),
 C24'(H24'), C25'(H25')
;
_olex2_submission_special_instructions 'No special instructions were received'