A concise synthetic approach to the sorbicillactones: total synthesis of sorbicillactone A and 9-epi-sorbicillactone A.
Volp, Kelly A.; Johnson, Diane M.; Harned, Andrew M.; Organic letters 13 (2011) 4486–4489; doi:10.1021/ol201211f

data_1502265
_publ_section_title
;
 A concise synthetic approach to the sorbicillactones: total synthesis of
 sorbicillactone A and 9-epi-sorbicillactone A.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4486
_journal_page_last               4489
_journal_paper_doi               10.1021/ol201211f
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C19 H20 Br N O5'
_chemical_formula_sum            'C19 H20 Br N O5'
_chemical_formula_weight         422.27
_chemical_name_common            10154
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                101.193(2)
_cell_angle_beta                 98.439(2)
_cell_angle_gamma                101.886(2)
_cell_formula_units_Z            2
_cell_length_a                   7.2726(13)
_cell_length_b                   11.545(2)
_cell_length_c                   11.673(2)
_cell_measurement_reflns_used    3565
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.15
_cell_measurement_theta_min      2.27
_cell_volume                     922.9(3)
_computing_cell_refinement       'SAINT, Bruker'
_computing_data_collection       'SMART, Bruker'
_computing_data_reduction        'SAINT, Bruker'
_computing_molecular_graphics    'SHELXTL, Bruker'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART Platform CCD'
_diffrn_measurement_method       'area detector, omega scans per phi'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_sigmaI/netI    0.0403
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10311
_diffrn_reflns_theta_full        26.42
_diffrn_reflns_theta_max         26.42
_diffrn_reflns_theta_min         1.81
_exptl_absorpt_coefficient_mu    2.257
_exptl_absorpt_correction_T_max  0.6610
_exptl_absorpt_correction_T_min  0.4300
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, R. Blessing, 1995'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.591
_refine_diff_density_min         -0.775
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3775
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0384
_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^)+(0.0402P)^2^+0.8311P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0861
_refine_ls_wR_factor_ref         0.1001
_reflns_number_gt                2743
_reflns_number_total             3775
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol201211f_si_002.cif
_cod_data_source_block           10154q
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1502265