Enantioselective palladium-catalyzed [3 + 2] cycloadditions of trimethylenemethane with nitroalkenes.
Trost, Barry M.; Bringley, Dustin A.; Seng, Pamela S.; Organic letters 14 (2012) 234–237; doi:10.1021/ol2030179

data_1503522
_publ_section_title
;
 Enantioselective palladium-catalyzed [3 + 2] cycloadditions of
 trimethylenemethane with nitroalkenes.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              234
_journal_page_last               237
_journal_paper_doi               10.1021/ol2030179
_journal_volume                  14
_journal_year                    2012
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C16 H14 Cl N O2'
_chemical_formula_sum            'C16 H14 Cl N O2'
_chemical_formula_weight         287.73
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.93800(10)
_cell_length_b                   7.9686(2)
_cell_length_c                   27.9472(6)
_cell_measurement_reflns_used    3933
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.34
_cell_measurement_theta_min      5.78
_cell_volume                     1322.39(5)
_computing_cell_refinement       'Bruker SAINT v7.66A'
_computing_data_collection       'Bruker APEX-II v2009-9'
_computing_data_reduction        'Bruker SAINT v7.66A'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX'
_diffrn_measurement_method       'combination of \w and \f-scans '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_sigmaI/netI    0.0302
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            12932
_diffrn_reflns_theta_full        69.67
_diffrn_reflns_theta_max         69.67
_diffrn_reflns_theta_min         3.16
_exptl_absorpt_coefficient_mu    2.562
_exptl_absorpt_correction_T_max  0.8873
_exptl_absorpt_correction_T_min  0.5917
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS, Sheldrick, 2008'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881, 992 Friedel Pairs measured'
_refine_ls_abs_structure_Flack   0.016(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2472
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0318
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0415P)^2^+0.4903P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0785
_refine_ls_wR_factor_ref         0.0808
_reflns_number_gt                2309
_reflns_number_total             2472
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol2030179_si_003.cif
_cod_data_source_block           su030
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               1503522