Catalytic enantioselective synthesis of chiral spirocyclic 1,3-diketones <i>via</i> organo-cation catalysis.
Zhang, Xiao-Yan; Shao, Ya-Ping; Guo, Bao-Kuan; Zhang, Kun; Zhang, Fu-Min; Zhang, Xiao-Ming; Tu, Yong-Qiang; Chemical communications (Cambridge, England) 57 (2021) 11233–11235; doi:10.1039/d1cc05205e

data_7129056
_publ_section_title
;
 Catalytic enantioselective synthesis of chiral spirocyclic 1,3-diketones
 <i>via</i> organo-cation catalysis.
;
_journal_issue                   85
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              11233
_journal_page_last               11235
_journal_paper_doi               10.1039/d1cc05205e
_journal_volume                  57
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C13 H11 Cl O2'
_chemical_formula_sum            'C13 H11 Cl O2'
_chemical_formula_weight         234.67
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2021-06-25
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2021-06-28 deposited with the CCDC.	2021-10-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.90260(14)
_cell_length_b                   6.93126(15)
_cell_length_c                   23.3243(4)
_cell_measurement_reflns_used    5980
_cell_measurement_temperature    293.0(7)
_cell_measurement_theta_max      76.0770
_cell_measurement_theta_min      3.7720
_cell_volume                     1115.92(4)
_computing_cell_refinement       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.105a (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 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.0(7)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.982
_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     33.00  66.00   0.50    0.30    --  104.25 -61.00  90.00   66
  2  \w     32.00  57.00   0.50    0.30    --  104.25 -61.00 -60.00   50
  3  \w     36.00  96.00   0.50    0.30    --  104.25 -77.00 -90.00  120
  4  \w     44.00  69.00   0.50    0.30    --  104.25 -61.00-150.00   50
  5  \w     64.00 171.00   0.50    0.30    --  104.25   7.00 -79.00  214
  6  \w    -16.00  18.00   0.50    0.10    --  -46.32  19.00-120.00   68
  7  \w    -24.00   8.00   0.50    0.10    --  -46.32  19.00 -30.00   64
  8  \w    -22.00  22.00   0.50    0.10    --  -46.32  19.00  60.00   88
  9  \w    -56.00 -30.00   0.50    0.30    -- -102.00  61.00 150.00   52
 10  \w    -64.00 -38.00   0.50    0.30    -- -102.00  61.00 120.00   52
 11  \w    -68.00 -43.00   0.50    0.30    -- -102.00  61.00   0.00   50
 12  \w   -114.00 -89.00   0.50    0.30    -- -102.00 -30.00-150.00   50
 13  \w   -117.00 -92.00   0.50    0.10    --  -46.32-138.00-123.00   50
 14  \w   -115.00 -71.00   0.50    0.30    -- -102.00-131.00  52.00   88
 15  \w   -156.00-120.00   0.50    0.30    -- -102.00-131.00  52.00   72
 16  \w   -174.00-136.00   0.50    0.30    -- -102.00 -30.00-150.00   76
 17  \w    -87.00 -49.00   0.50    0.30    -- -102.00 123.00  38.00   76
 18  \w     31.00  72.00   0.50    0.10    --   46.32-149.00 154.00   82
 19  \w     77.00 109.00   0.50    0.10    --   46.32-149.00 154.00   64
 20  \w     33.00  58.00   0.50    0.30    --  104.25 -94.00-120.00   50
 21  \w     76.00 106.00   0.50    0.30    --  104.25 -94.00-120.00   60
 22  \w   -120.00 -87.00   0.50    0.30    -- -102.00 138.00 -60.00   66
 23  \w    -35.00   7.00   0.50    0.10    --  -46.32  37.00 -30.00   84
 24  \w    -13.00  28.00   0.50    0.10    --  -46.32   7.00 -79.00   82
 25  \w   -100.00 -50.00   0.50    0.10    --  -46.32  -7.00 104.00  100
 26  \w    -19.00   7.00   0.50    0.10    --  -46.32  19.00 -60.00   52
 27  \w     58.00  97.00   0.50    0.30    --  104.25-125.00-120.00   78
 28  \w    149.00 176.00   0.50    0.30    --  104.25  45.00 150.00   54
 29  \w     97.00 123.00   0.50    0.30    --  104.25 125.00  90.00   52
 30  \w     73.00  99.00   0.50    0.30    --  104.25 -94.00 -90.00   52
 31  \w    100.00 125.00   0.50    0.30    --  104.25  45.00 150.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0081287000
_diffrn_orient_matrix_UB_12      0.0208962000
_diffrn_orient_matrix_UB_13      0.0657141000
_diffrn_orient_matrix_UB_21      0.2229002000
_diffrn_orient_matrix_UB_22      0.0053192000
_diffrn_orient_matrix_UB_23      -0.0025746000
_diffrn_orient_matrix_UB_31      -0.0060850000
_diffrn_orient_matrix_UB_32      0.2212591000
_diffrn_orient_matrix_UB_33      -0.0061627000
_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  0.0237
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            8732
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.180
_diffrn_reflns_theta_min         3.790
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.876
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80911
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.105a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 763 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.000(8)
_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     145
_refine_ls_number_reflns         2262
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0335
_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^)+(0.0481P)^2^+0.1060P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0862
_refine_ls_wR_factor_ref         0.0884
_reflns_Friedel_coverage         0.650
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.932
_reflns_number_gt                2080
_reflns_number_total             2262
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc05205e2.cif
_cod_data_source_block           zhangxiaoyan_0623-2_auto
_cod_depositor_comments
'Adding full bibliography for 7129056--7129057.cif.'
_cod_database_code               7129056
_shelx_shelxl_version_number     2018/1
_reflns_odcompleteness_completeness 100.00
_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 Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C12(H12)
;
_shelx_res_checksum              98638
_shelx_hkl_checksum              29855
_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 1.377
_oxdiff_exptl_absorpt_empirical_full_min 0.646