Total Synthesis and Structural Revision of the Piperarborenines via Sequential Cyclobutane C-H Arylation
Will R. Gutekunst; Phil S. Baran; Journal of the American Chemical Society 133 (2011) 19076–19079; doi:10.1021/ja209205x

data_4107174
_publ_section_title
;
 Total Synthesis and Structural Revision of the Piperarborenines via
 Sequential Cyclobutane C-H Arylation
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              19076
_journal_page_last               19079
_journal_paper_doi               10.1021/ja209205x
_journal_volume                  133
_journal_year                    2011
_chemical_formula_sum            'C23 H27 N O6 S'
_chemical_formula_weight         445.52
_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                 99.32
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.6275(4)
_cell_length_b                   8.5892(3)
_cell_length_c                   20.4658(6)
_cell_measurement_reflns_used    7528
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      25.39
_cell_measurement_theta_min      2.58
_cell_volume                     2190.42(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_sigmaI/netI    0.0238
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            13669
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.39
_diffrn_reflns_theta_min         1.63
_exptl_absorpt_coefficient_mu    0.188
_exptl_absorpt_correction_T_max  0.9778
_exptl_absorpt_correction_T_min  0.9253
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         4017
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0340
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0340P)^2^+1.3000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0815
_refine_ls_wR_factor_ref         0.0857
_reflns_number_gt                3608
_reflns_number_total             4017
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja209205x_si_003.cif
_cod_data_source_block           baran181
_cod_original_cell_volume        2190.39(12)
_cod_database_code               4107174