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_7129057
_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_formula_moiety         'C13 H11 Cl O2'
_chemical_formula_sum            'C13 H11 Cl O2'
_chemical_formula_weight         234.67
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2020-06-10
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2021-07-28 deposited with the CCDC.	2021-10-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.577(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.6872(8)
_cell_length_b                   6.0620(3)
_cell_length_c                   14.0247(9)
_cell_measurement_reflns_used    1150
_cell_measurement_temperature    292.69(10)
_cell_measurement_theta_max      68.4680
_cell_measurement_theta_min      6.7020
_cell_volume                     1120.91(12)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.69(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_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     49.00 142.00   1.00    1.00    --  108.00 -25.00   0.00   93
  2  \w     74.00 167.00   1.00    1.00    --  108.00  25.00  30.00   93
  3  \w     68.00 116.00   1.00    1.00    --  108.00-111.00 -30.00   48
  4  \w     77.00 108.00   1.00    1.00    --  108.00-111.00-180.00   31
  5  \w     41.00  66.00   1.00    1.00    --  108.00-111.00-180.00   25
  6  \w     41.00 138.00   1.00    1.00    --  108.00 -77.00   0.00   97
  7  \w     55.00 123.00   1.00    1.00    --   54.00  57.00  60.00   68
  8  \w     66.00 106.00   1.00    1.00    --  108.00 178.00 -90.00   40
  9  \w    138.00 163.00   1.00    1.00    --  108.00 111.00-180.00   25
 10  \w     28.00  95.00   1.00    1.00    --   54.00 -99.00  30.00   67
 11  \w    -21.00  51.00   1.00    1.00    --    0.00  57.00  30.00   72
 12  \w     29.00 124.00   1.00    1.00    --   54.00  77.00 150.00   95
 13  \w    -12.00  47.00   1.00    1.00    --    0.00  57.00 120.00   59
 14  \w    -18.00  23.00   1.00    1.00    --   54.00 -38.00  90.00   41
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0441732000
_diffrn_orient_matrix_UB_12      0.0425527000
_diffrn_orient_matrix_UB_13      -0.1116023000
_diffrn_orient_matrix_UB_21      0.1081517000
_diffrn_orient_matrix_UB_22      0.0257227000
_diffrn_orient_matrix_UB_23      -0.0117448000
_diffrn_orient_matrix_UB_31      0.0036035000
_diffrn_orient_matrix_UB_32      -0.2492048000
_diffrn_orient_matrix_UB_33      -0.0202420000
_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  0.0217
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3650
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.600
_diffrn_reflns_theta_max         66.600
_diffrn_reflns_theta_min         4.007
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.863
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80882
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.391
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1975
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0460
_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^)+(0.0686P)^2^+0.1047P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1158
_refine_ls_wR_factor_ref         0.1323
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1492
_reflns_number_total             1975
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc05205e2.cif
_cod_data_source_block           zhangxy_0604
_cod_depositor_comments
'Adding full bibliography for 7129056--7129057.cif.'
_cod_database_code               7129057
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.894
_shelx_estimated_absorpt_t_min   0.763
_reflns_odcompleteness_completeness 99.82
_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:
 C4(H4A,H4B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C12(H12), C13(H13)
;
_shelx_res_checksum              40610
_shelx_hkl_checksum              61748
_olex2_date_sample_data_collection 2020-06-04
_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 1.400
_oxdiff_exptl_absorpt_empirical_full_min 0.680