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_7133993
_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_absolute_configuration ad
_chemical_formula_moiety         'C31 H23 N O2'
_chemical_formula_sum            'C31 H23 N O2'
_chemical_formula_weight         441.50
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-05-28
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-10-16 deposited with the CCDC.	2024-11-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   26.0297(16)
_cell_length_b                   5.9625(3)
_cell_length_c                   15.3428(9)
_cell_measurement_reflns_used    6834
_cell_measurement_temperature    303.00
_cell_measurement_theta_max      24.46
_cell_measurement_theta_min      2.66
_cell_volume                     2381.2(2)
_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      303.00
_diffrn_measured_fraction_theta_full 0.998
_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  0.0607
_diffrn_reflns_av_unetI/netI     0.0471
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            26654
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.287
_diffrn_reflns_theta_min         2.655
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0914 before and 0.0738 after correction.
The Ratio of minimum to maximum transmission is 0.9494.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.121
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         5846
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0451
_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^)+(0.0367P)^2^+0.2499P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.1099
_reflns_Friedel_coverage         0.922
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                4453
_reflns_number_total             5846
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc05895j2.cif
_cod_data_source_block           mo_240526zzl_0ma
_cod_depositor_comments
'Adding full bibliography for 7133991--7133993.cif.'
_cod_database_code               7133993
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.985
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 1(2)
 0(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C24(H24), C13(H13), C6(H6), C4(H4), C17(H17), C27(H27), C3(H3), C19(H19),
 C7(H7), C31(H31), C22(H22), C14(H14), C23(H23), C16(H16), C20(H20), C28(H28),
 C21(H21), C15(H15), C30(H30), C29(H29)
3.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              14161
_shelx_hkl_checksum              33498
_olex2_submission_special_instructions 'No special instructions were received'