Diastereoselective, Lewis acid-mediated Diels-Alder reactions of allenoic acid derivatives and 1,3-cyclopentadienes.
Harvey, Freya M.; Heidecker, Alexandra H.; Merten, Christian; Bach, Thorsten; Organic & biomolecular chemistry 21 (2023) 4422–4428; doi:10.1039/d3ob00598d

data_7159345
_publ_section_title
;
 Diastereoselective, Lewis acid-mediated Diels-Alder reactions of allenoic
 acid derivatives and 1,3-cyclopentadienes.
;
_journal_issue                   21
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4422
_journal_page_last               4428
_journal_paper_doi               10.1039/d3ob00598d
_journal_volume                  21
_journal_year                    2023
_chemical_compound_source        'see text'
_chemical_formula_moiety         'C25 H31 N O2'
_chemical_formula_sum            'C25 H31 N O2'
_chemical_formula_weight         377.51
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2023-03-07 deposited with the CCDC.	2023-05-08 downloaded from the CCDC.
;
_cell_angle_alpha                115.040(3)
_cell_angle_beta                 94.445(3)
_cell_angle_gamma                99.671(3)
_cell_formula_units_Z            2
_cell_length_a                   10.2906(8)
_cell_length_b                   10.4146(8)
_cell_length_c                   10.5305(7)
_cell_measurement_reflns_used    9799
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.3102
_cell_measurement_theta_min      2.2138
_cell_volume                     993.93(13)
_computing_cell_refinement       'SAINT (Bruker, 2019)'
_computing_data_collection       'APEX 4 Control Software (Bruker, 2021)'
_computing_data_reduction        'SAINT (Bruker, 2019)'
_computing_molecular_graphics    'PLATON (Spek, 2011)'
_computing_publication_material  'PLATON (Spek, 2011), enCIFer (Allen, 2004)'
_computing_structure_refinement
'SHELXL (Sheldrick, 2018), SHELXLE (Huebschle, 2011)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 ' Bruker Photon-II CPAD '
_diffrn_detector_area_resol_mean 16
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       ' \k-geometry diffractometer '
_diffrn_measurement_device_type  ' Bruker D8 Venture '
_diffrn_measurement_method       ' phi- and omega-rotation '
_diffrn_radiation_monochromator  'Helios optic'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'TXS rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0562
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            55199
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         27.88
_diffrn_reflns_theta_min         2.31
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6874
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2016/2, Bruker, 2016'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.152
_exptl_crystal_size_mid          0.137
_exptl_crystal_size_min          0.129
_refine_diff_density_max         0.519
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         4723
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0480
_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^)+(0.0699P)^2^+0.3783P] WHERE P=(FO^2^+2FC^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1224
_refine_ls_wR_factor_ref         0.1274
_reflns_number_gt                4255
_reflns_number_total             4723
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            d3ob00598d2.cif
_cod_data_source_block           harfr2_0m
_cod_depositor_comments          'Adding full bibliography for 7159345.cif.'
_cod_database_code               7159345
_shelx_res_checksum              29992