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_7118944
_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_absolute_configuration unk
_chemical_formula_moiety         'C16 H14 N2 O'
_chemical_formula_sum            'C16 H14 N2 O'
_chemical_formula_weight         250.29
_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   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-03-16 deposited with the CCDC.
2016-03-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.4060(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.0535(2)
_cell_length_b                   7.4148(2)
_cell_length_c                   10.4203(3)
_cell_measurement_reflns_used    9742
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      67.65
_cell_measurement_theta_min      4.38
_cell_volume                     677.52(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis,2007)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'multi layer miror'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0171
_diffrn_reflns_av_unetI/netI     0.0136
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12413
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.659
_diffrn_reflns_theta_max         67.659
_diffrn_reflns_theta_min         5.044
_diffrn_source                   'micro focus sealed tube'
_exptl_absorpt_coefficient_mu    0.619
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_correction_T_min  0.707
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS, Bruker AXS Inc., Madison, 
Wisconsin, USA. 
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate-like
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.123
_refine_diff_density_min         -0.117
_refine_diff_density_rms         0.023
_refine_ls_abs_structure_details
;
 Flack x determined using 1094 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.17(11)
_refine_ls_extinction_coef       0.0144(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2436
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.138
_refine_ls_R_factor_all          0.0255
_refine_ls_R_factor_gt           0.0253
_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^)+(0.0285P)^2^+0.0783P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0644
_refine_ls_wR_factor_ref         0.0646
_reflns_Friedel_coverage         0.836
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                2418
_reflns_number_total             2436
_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               7118944
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              53037
_shelx_hkl_checksum              17350