Through-Shell Alkyllithium Additions and Borane Reductions
Ralf Warmuth; Emily F. Maverick; Carolyn B. Knobler; Donald J. Cram; Journal of Organic Chemistry 68 (2003) 2077–2088; doi:10.1021/jo026649z

data_4022324
_publ_section_title
;
 Through-Shell Alkyllithium Additions and Borane Reductions
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2077
_journal_page_last               2088
_journal_paper_doi               10.1021/jo026649z
_journal_volume                  68
_journal_year                    2003
_chemical_formula_moiety         '(C144 H136 O24).(C8 H6 O1).2(C6 H5 N1 O2)'
_chemical_formula_sum            'C164 H152 N2 O29'
_chemical_formula_weight         2614.88
_chemical_name_common            'benzocyclobutenone hemicarceplex'
_chemical_name_systematic
;
  ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 98.998(16)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   16.650(11)
_cell_length_b                   20.442(14)
_cell_length_c                   20.043(13)
_cell_measurement_reflns_used    34
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      14.2
_cell_measurement_theta_min      8.3
_cell_volume                     6738(8)
_computing_cell_refinement       'LEAST (UCLA crystallographic package)'
_computing_data_reduction        'REDUCE (UCLA crystallographic package)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELX86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Syntex Diffractometer (Crystal Logic)'
_diffrn_measurement_method       'profile data from \q/2\q scans'
_diffrn_radiation_detector       scintillation
_diffrn_radiation_detector_dtime 3.5
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0678
_diffrn_reflns_av_sigmaI/netI    0.0972
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7017
_diffrn_reflns_reduction_process 'modified Lehmann-Larsen algorithm'
_diffrn_reflns_theta_full        50.00
_diffrn_reflns_theta_max         50.00
_diffrn_reflns_theta_min         2.69
_diffrn_standards_decay_%        -2.0
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.713
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             2764
_exptl_crystal_preparation       fiber
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.732
_refine_diff_density_min         -0.509
_refine_diff_density_rms         0.100
_refine_ls_extinction_coef       0.00015(19)
_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   1.668
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         6721
_refine_ls_number_restraints     32
_refine_ls_restrained_S_all      1.674
_refine_ls_R_factor_all          0.2832
_refine_ls_R_factor_gt           0.1718
_refine_ls_shift/su_max          0.020
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4560
_refine_ls_wR_factor_ref         0.5219
_reflns_number_gt                2965
_reflns_number_total             6721
_reflns_threshold_expression     >2sigma(I)
_cod_duplicate_entry             4022322
_cod_data_source_file            jo026649z_s3.cif
_cod_data_source_block           rwc2
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4022324