Pd(II)-catalyzed regioselective ring opening/[3+2] annulation reaction of enaminones with cyclopropenones: divergent synthesis of γ-butenolides and γ-lactams.
Zhang, Zhilai; Xu, Yu; Peng, Menglin; Song, Siyu; Wei, Yuanzheng; Hu, Huimin; Wang, Xiuju; Yu, Fuchao; Chemical communications (Cambridge, England) 60 (2024) 14968–14971; doi:10.1039/d4cc05895j

data_7133991
_publ_section_title
;
 Pd(II)-catalyzed regioselective ring opening/[3+2] annulation reaction of
 enaminones with cyclopropenones: divergent synthesis of
 &#x3b3;-butenolides and &#x3b3;-lactams.
;
_journal_issue                   100
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              14968
_journal_page_last               14971
_journal_paper_doi               10.1039/d4cc05895j
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C25 H20 O3'
_chemical_formula_sum            'C25 H20 O3'
_chemical_formula_weight         368.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-06-27
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-08-16 deposited with the CCDC.	2024-11-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.829(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2274(4)
_cell_length_b                   13.5230(5)
_cell_length_c                   14.2522(7)
_cell_measurement_reflns_used    9954
_cell_measurement_temperature    300.00
_cell_measurement_theta_max      28.18
_cell_measurement_theta_min      2.50
_cell_volume                     1970.95(14)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      300.00
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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  0.0726
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            53825
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.302
_diffrn_reflns_theta_min         1.991
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6940
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1165 before and 0.0645 after correction.
The Ratio of minimum to maximum transmission is 0.9307.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         4901
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0438
_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^)+(0.0623P)^2^+0.3160P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1161
_refine_ls_wR_factor_ref         0.1303
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3684
_reflns_number_total             4901
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc05895j2.cif
_cod_data_source_block           mo_240626zzl_0m
_cod_depositor_comments
'Adding full bibliography for 7133991--7133993.cif.'
_cod_database_code               7133991
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.984
_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 Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C18(H18), C9(H9), C3(H3), C13(H13), C24(H24), C22(H22), C19(H19), C2(H2),
 C12(H12), C10(H10), C11(H11), C20(H20), C25(H25), C1(H1), C21(H21)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_shelx_res_checksum              83916
_shelx_hkl_checksum              54240
_olex2_submission_special_instructions 'No special instructions were received'