Accessing polysubstituted 2-cyclopentenones <i>via</i> base-mediated annulation of β-keto esters and phenacyl bromides.
Kumar, Mohit; Paul, Vincent; Gamidi, Rama Krishna; Senthilkumar, Beeran; Organic & biomolecular chemistry 23 (2025) 4519–4524; doi:10.1039/d4ob02088j

data_7160490
_publ_section_title
;
 Accessing polysubstituted 2-cyclopentenones <i>via</i> base-mediated
 annulation of &#x3b2;-keto esters and phenacyl bromides.
;
_journal_issue                   18
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4519
_journal_page_last               4524
_journal_paper_doi               10.1039/d4ob02088j
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         '2(C20 H17 F3 O5)'
_chemical_formula_sum            'C40 H34 F6 O10'
_chemical_formula_weight         788.67
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2023-07-27
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-07-27 deposited with the CCDC.	2025-04-02 downloaded from the CCDC.
;
_cell_angle_alpha                83.603(6)
_cell_angle_beta                 82.238(6)
_cell_angle_gamma                89.317(7)
_cell_formula_units_Z            1
_cell_length_a                   5.5852(10)
_cell_length_b                   8.4012(14)
_cell_length_c                   18.790(3)
_cell_measurement_reflns_used    9688
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      2.30
_cell_volume                     868.1(3)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      103.00
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            31105
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_min         2.563
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_description       Plate
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.042(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3759
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0324
_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^)+(0.0372P)^2^+0.4073P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0820
_refine_ls_wR_factor_ref         0.0844
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3473
_reflns_number_total             3759
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob02088j2.cif
_cod_data_source_block           mkv55b
_cod_depositor_comments
'Adding full bibliography for 7160489--7160491.cif.'
_cod_original_cell_volume        868.2(3)
_cod_database_code               7160490
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C10(H10), C11(H11), C17(H17), C20(H20)
2.d Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C12(H12A,H12B,H12C)
;
_shelx_res_checksum              71096
_olex2_submission_special_instructions 'No special instructions were received'