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_4114933
_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            'C25 H33 N O4'
_chemical_formula_weight         411.52
_space_group_IT_number           92
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4abw 2nw'
_symmetry_space_group_name_H-M   'P 41 21 2'
_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            8
_cell_length_a                   9.416(2)
_cell_length_b                   9.416(2)
_cell_length_c                   51.331(14)
_cell_measurement_reflns_used    55
_cell_measurement_temperature    213(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      15
_cell_volume                     4551.1(18)
_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      213(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0337
_diffrn_reflns_av_sigmaI/netI    0.0372
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -57
_diffrn_reflns_number            4261
_diffrn_reflns_theta_full        59.98
_diffrn_reflns_theta_max         59.98
_diffrn_reflns_theta_min         3.44
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  120
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.643
_exptl_absorpt_correction_T_max  0.8305
_exptl_absorpt_correction_T_min  0.7393
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1776
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.7(5)
_refine_ls_extinction_coef       0.0001(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         3389
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0933
_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^)+(0.0979P)^2^+0.8445P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1625
_refine_ls_wR_factor_ref         0.1863
_reflns_number_gt                2381
_reflns_number_total             3389
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0122288_1.cif
_cod_data_source_block           berg06
_cod_original_cell_volume        4551.0(19)
_cod_database_code               4114933