Asymmetric preparation of polysubstituted cyclopentanes by synergistic Pd(0)/amine catalyzed formal [3+2] cycloadditions of vinyl cyclopropanes with enals.
Laugeois, Maxime; Ponra, Sudipta; Ratovelomanana-Vidal, Virginie; Michelet, Véronique; Vitale, Maxime R.; Chemical communications (Cambridge, England) 52 (2016) 5332–5335; doi:10.1039/c6cc01775d

data_7118945
_publ_section_title
;
 Asymmetric preparation of polysubstituted cyclopentanes by synergistic
 Pd(0)/amine catalyzed formal [3+2] cycloadditions of vinyl cyclopropanes
 with enals.
;
_journal_issue                   30
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5332
_journal_page_last               5335
_journal_paper_doi               10.1039/c6cc01775d
_journal_volume                  52
_journal_year                    2016
_chemical_formula_sum            'C16 H16 N2 O'
_chemical_formula_weight         252.31
_chemical_name_systematic
(1S,5R,6R,8S)-2-imino-8-phenyl-6-vinyl-3-oxabicyclo[3.2.1]octane-1-carbonitrile
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-02-26 deposited with the CCDC.
2016-03-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.885(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.9841(7)
_cell_length_b                   12.5978(13)
_cell_length_c                   15.7350(16)
_cell_measurement_temperature    200(2)
_cell_volume                     1371.3(2)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.980
_diffrn_radiation_type           CuK\a
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_diffrn_reflns_av_unetI/netI     0.0654
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -18
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_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.161
_diffrn_reflns_theta_min         2.835
_exptl_absorpt_coefficient_mu    0.612
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_F_000             536
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.6(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         4790
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0998
_refine_ls_R_factor_gt           0.0772
_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^)+(0.1632P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2313
_refine_ls_wR_factor_ref         0.2498
_reflns_Friedel_coverage         0.909
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                3486
_reflns_number_total             4790
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc01775d2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 7118943--7118945.cif.'
_cod_database_code               7118945
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              9527
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