Highly Enantioselective Intra- and Intermolecular [2 + 2] Photocycloaddition Reactions of 2-Quinolones Mediated by a Chiral Lactam Host: Host-Guest Interactions, Product Configuration, and the Origin of the Stereoselectivity in Solution
Thorsten Bach; Hermann Bergmann; Benjamin Grosch; Klaus Harms; Journal of the American Chemical Society 124 (2002) 7982–7990; doi:10.1021/ja0122288

data_4114934
_publ_section_title
;
 Highly Enantioselective Intra- and Intermolecular [2 + 2]
 Photocycloaddition Reactions of 2-Quinolones Mediated by a Chiral Lactam
 Host: Host-Guest Interactions, Product Configuration, and the Origin of
 the Stereoselectivity in Solution
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7982
_journal_page_last               7990
_journal_paper_doi               10.1021/ja0122288
_journal_volume                  124
_journal_year                    2002
_chemical_formula_sum            'C21 H33 N O3 Si'
_chemical_formula_weight         375.57
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                98.570(10)
_cell_angle_beta                 105.090(10)
_cell_angle_gamma                97.310(10)
_cell_formula_units_Z            2
_cell_length_a                   7.6650(10)
_cell_length_b                   11.6440(10)
_cell_length_c                   12.6060(10)
_cell_measurement_temperature    203(2)
_cell_volume                     1057.8(2)
_computing_cell_refinement       'CAD4 EXPRESS'
_computing_data_collection       'CAD4 EXPRESS'
_computing_data_reduction        'XCAD4 (Harms, 1997)'
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'Siemens SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      203(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       Omega-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  0.0205
_diffrn_reflns_av_sigmaI/netI    0.0454
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4313
_diffrn_reflns_theta_full        70.13
_diffrn_reflns_theta_max         70.13
_diffrn_reflns_theta_min         3.70
_diffrn_standards_decay_%        4
_diffrn_standards_interval_time  120
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    1.128
_exptl_absorpt_correction_T_max  0.8228
_exptl_absorpt_correction_T_min  0.5811
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.179
_exptl_crystal_description       Prism
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.452
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3995
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0906
_refine_ls_R_factor_gt           0.0628
_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^)+(0.0937P)^2^+0.1606P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1558
_refine_ls_wR_factor_ref         0.1756
_reflns_number_gt                2877
_reflns_number_total             3995
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0122288_2.cif
_cod_data_source_block           berg11
_cod_original_cell_volume        1057.81(19)
_cod_database_code               4114934