Scalable, Stereocontrolled Total Syntheses of (\±)-Axinellamines A and B
Shun Su; Rodrigo A. Rodriguez; Phil S. Baran; Journal of the American Chemical Society 133 (2011) 13922–13925; doi:10.1021/ja206191g

data_4106729
_publ_section_title
;
 Scalable, Stereocontrolled Total Syntheses of (\+-)-Axinellamines A and B
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13922
_journal_page_last               13925
_journal_paper_doi               10.1021/ja206191g
_journal_volume                  133
_journal_year                    2011
_chemical_formula_sum            'C15 H17 Cl F6 N10 O4'
_chemical_formula_weight         550.84
_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                 98.636(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.6055(10)
_cell_length_b                   21.324(3)
_cell_length_c                   14.1065(18)
_cell_measurement_reflns_used    9941
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.86
_cell_measurement_theta_min      2.40
_cell_volume                     2261.8(5)
_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, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_device_type  'Bruker APEX 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  0.0353
_diffrn_reflns_av_sigmaI/netI    0.0254
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            32765
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.94
_diffrn_reflns_theta_min         1.74
_exptl_absorpt_coefficient_mu    0.265
_exptl_absorpt_correction_T_max  0.9715
_exptl_absorpt_correction_T_min  0.9131
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.655
_refine_diff_density_min         -0.466
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         5194
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0411
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0422P)^2^+1.7188P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0960
_refine_ls_wR_factor_ref         0.1027
_reflns_number_gt                4265
_reflns_number_total             5194
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja206191g_si_003.cif
_cod_data_source_block           baran210
_cod_original_cell_volume        2261.9(5)
_cod_database_code               4106729