Organocatalytic enantioselective desymmetrization of enal-tethered cyclohexane-1,3-diones.
Magham, Lakshmi Revati; Samad, Abdus; Thopate, Satish B.; Nanubolu, Jagadeesh Babu; Chegondi, Rambabu; Chemical communications (Cambridge, England) 60 (2024) 3834–3837; doi:10.1039/d4cc00487f

data_7132809
_publ_section_title
;
 Organocatalytic enantioselective desymmetrization of enal-tethered
 cyclohexane-1,3-diones.
;
_journal_issue                   28
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3834
_journal_page_last               3837
_journal_paper_doi               10.1039/d4cc00487f
_journal_volume                  60
_journal_year                    2024
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C20 H22 O2'
_chemical_formula_sum            'C20 H22 O2'
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_space_group_crystal_system      monoclinic
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_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2023-09-20 deposited with the CCDC.	2024-03-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
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_cell_angle_gamma                90
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_cell_length_b                   6.518(3)
_cell_length_c                   15.600(8)
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_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.191
_cell_measurement_theta_min      2.479
_cell_volume                     837.7(7)
_computing_cell_refinement       '<i>SAINT</i> (Bruker, 2016)'
_computing_data_collection       '<i>APEX3</i> (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON III C7 HPAD'
_diffrn_measurement_method       '\w and \f'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_unetI/netI     0.0555
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            17575
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.515
_diffrn_reflns_theta_min         2.472
_diffrn_source                   microfocus
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6267
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_description       NEEDLE
_exptl_crystal_F_000             316
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM/hexane (3:2)'
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 1397 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         5101
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0440
_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^)+(0.0393P)^2^+0.0904P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0899
_refine_ls_wR_factor_ref         0.1003
_reflns_Friedel_coverage         0.841
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                3824
_reflns_number_total             5101
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc00487f2.cif
_cod_data_source_block           KB690_0m
_cod_depositor_comments          'Adding full bibliography for 7132809.cif.'
_cod_original_cell_volume        837.6(7)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7132809
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_min   0.981
_shelx_estimated_absorpt_t_max   0.991
_shelx_res_checksum              99833
_shelx_hkl_checksum              52666