CuH-catalyzed stereoselective desymmetrization of prochiral cyclopentane-1,3-diones <i>via</i> alkoxyallylation.
Maurya, Sundaram; Patil, Vaibhav B.; Raghu Ramudu, G.; Amrutkar, Virendra S.; Mendapara, Yash G.; Nanubolu, Jagadeesh Babu; Chegondi, Rambabu; Chemical communications (Cambridge, England) 61 (2025) 19108–19111; doi:10.1039/d5cc05400a

data_7135118
_publ_section_title
;
 CuH-catalyzed stereoselective desymmetrization of prochiral
 cyclopentane-1,3-diones <i>via</i> alkoxyallylation.
;
_journal_issue                   96
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              19108
_journal_page_last               19111
_journal_paper_doi               10.1039/d5cc05400a
_journal_volume                  61
_journal_year                    2025
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C25 H28 O3'
_chemical_formula_sum            'C25 H28 O3'
_chemical_formula_weight         376.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2025-08-29 deposited with the CCDC.	2025-10-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.8422(17)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.4261(4)
_cell_length_b                   11.7773(6)
_cell_length_c                   11.2319(6)
_cell_measurement_reflns_used    9472
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      28.201
_cell_measurement_theta_min      2.573
_cell_volume                     1061.01(9)
_computing_cell_refinement       'SAINT V8.41 (Bruker AXS LLC, 2019)'
_computing_data_collection       'Bruker APEX5 v2023.9-0'
_computing_data_reduction        'SAINT V8.41 (Bruker AXS LLC, 2019)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON C14 HPAD'
_diffrn_measurement_method       '\w and \f'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            21019
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.297
_diffrn_reflns_theta_min         1.905
_diffrn_source                   microfocus
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6731
_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    1.178
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             404
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Chloroform and Hexane (1:1)'
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details
;
 Flack x determined using 2124 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         5272
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0356
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0575P)^2^+0.0447P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.1001
_reflns_Friedel_coverage         0.906
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                4830
_reflns_number_total             5272
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc05400a2.cif
_cod_data_source_block           mo_VA262_0m
_cod_depositor_comments
'Adding full bibliography for 7135117--7135118.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7135118
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_min   0.984
_shelx_estimated_absorpt_t_max   0.989
_shelx_res_checksum              16047