Structural Distortions and Dynamic Behavior of the Elusive "L"-Shaped cis-Bicyclo[3.3.0]octenyllithium: X-ray Crystallographic and NMR Studies
Gideon Fraenkel; Xiao Chen; Judith Gallucci; Yan Lu; Journal of Organic Chemistry 72 (2007) 4961–4965; doi:10.1021/jo0706022

data_4023967
_publ_section_title
;
 Structural Distortions and Dynamic Behavior of the Elusive
 "L"-Shaped cis-Bicyclo[3.3.0]octenyllithium: X-ray Crystallographic
 and NMR Studies
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4961
_journal_page_last               4965
_journal_paper_doi               10.1021/jo0706022
_journal_volume                  72
_journal_year                    2007
_chemical_absolute_configuration unk
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C32 H58 Li2 N2'
_chemical_formula_sum            'C32 H58 Li2 N2'
_chemical_formula_weight         484.68
_chemical_name_common            'Fraenkel 1469'
_chemical_name_systematic
;
  ?
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      9
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2006-12-07T12:43:25-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 99.110(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.3719(10)
_cell_length_b                   17.364(2)
_cell_length_c                   16.532(3)
_cell_measurement_reflns_used    2954
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.028
_cell_measurement_theta_min      2.037
_cell_measurement_wavelength     0.71073
_cell_volume                     3223.4(7)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'Nonius KappaCCD'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi and omega scans'
_diffrn_orient_matrix_type       'by Nonius Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      0.378715E-1
_diffrn_orient_matrix_UB_12      -0.804405E-1
_diffrn_orient_matrix_UB_13      0.51647E-2
_diffrn_orient_matrix_UB_21      -0.4632E-3
_diffrn_orient_matrix_UB_22      0.34726E-2
_diffrn_orient_matrix_UB_23      0.574821E-1
_diffrn_orient_matrix_UB_31      -0.506192E-1
_diffrn_orient_matrix_UB_32      -0.344629E-1
_diffrn_orient_matrix_UB_33      0.1674E-2
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.030
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            23008
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         2.16
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    0.056
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    0.999
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chunk
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.38
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     358
_refine_ls_number_reflns         2856
_refine_ls_number_restraints     11
_refine_ls_restrained_S_all      1.07
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0544
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0813P)^2^+2.5408P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1396
_refine_ls_wR_factor_ref         0.1471
_reflns_number_gt                2516
_reflns_number_total             2856
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0706022si20070403_091600.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               4023967