Total Synthesis of Herbicidin C and Aureonuclemycin: Impasses and New Avenues
Dominik Hager; Christian Paulitz; Jörg Tiebes; Peter Mayer; Dirk Trauner; Journal of Organic Chemistry 78 (2013) 10784–10801; doi:10.1021/jo401706r

data_4028707
_publ_section_title
;
 Total Synthesis of Herbicidin C and Aureonuclemycin: Impasses and New
 Avenues
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10784
_journal_page_last               10801
_journal_paper_doi               10.1021/jo401706r
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C14 H21 Br O7'
_chemical_formula_sum            'C14 H21 Br O7'
_chemical_formula_weight         381.216
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_code                C14H21BrO7_no182_trauner
_audit_creation_date
;
'Thu Sep 24 12:58:04 2009'
;
_audit_creation_method           'form98_non/compatible with shelxl97-2'
_audit_update_record             24-Sep-09
_cell_angle_alpha                90.00
_cell_angle_beta                 97.090(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.1405(5)
_cell_length_b                   9.1003(3)
_cell_length_c                   14.1366(4)
_cell_measurement_reflns_used    3075
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.2484
_cell_measurement_theta_min      4.2346
_cell_volume                     1677.56(10)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May 6 2009,17:20:42)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May 6 2009,17:20:42)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May 6 2009,17:20:42)
;
_computing_structure_refinement
'SHELXL-97 (G. M. Sheldrick. University of G\"ottingen, 97-2 version)'
_computing_structure_solution
;
A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A.
Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna: SIR97: a new tool for
crystal structure determination and refinement; J. Appl. Crystallogr. 1999,
32, 115-119.
;
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 15.9809
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
1 omega -52.00 53.00 1.0000 11.0000
omega____ theta____ kappa____ phi______ frames
- -20.7306 38.0000 -180.0000 105

2 omega -45.00 54.00 1.0000 11.0000
omega____ theta____ kappa____ phi______ frames
- 20.8868 -77.0000 30.0000 99

3 omega 22.00 54.00 1.0000 11.0000
omega____ theta____ kappa____ phi______ frames
- 20.8868 -77.0000 150.0000 32

;
_diffrn_measurement_device       'CCD camera on \k-goniostat'
_diffrn_measurement_device_type  'Oxford XCalibur'
_diffrn_measurement_method       omega-scans
_diffrn_orient_matrix_UB_11      -0.0442452767
_diffrn_orient_matrix_UB_12      -0.0401736032
_diffrn_orient_matrix_UB_13      0.0083569452
_diffrn_orient_matrix_UB_21      -0.0290235150
_diffrn_orient_matrix_UB_22      0.0659243433
_diffrn_orient_matrix_UB_23      -0.0028823985
_diffrn_orient_matrix_UB_31      -0.0125140324
_diffrn_orient_matrix_UB_32      -0.0106634658
_diffrn_orient_matrix_UB_33      -0.0497951598
_diffrn_radiation_collimation    '0.5 mm collimator'
_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  0.0251
_diffrn_reflns_av_sigmaI/netI    0.0887
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6923
_diffrn_reflns_theta_full        26.33
_diffrn_reflns_theta_max         26.33
_diffrn_reflns_theta_min         4.24
_diffrn_source_current           40_mA
_diffrn_source_power             2.00_kW
_diffrn_source_type              'Spellman generator'
_diffrn_source_voltage           50_kV
_exptl_absorpt_coefficient_mu    2.480
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May 6 2009,17:20:42)
empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.50942(9)
_exptl_crystal_description       platelet
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.125
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.016(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.869
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     405
_refine_ls_number_reflns         5174
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.869
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0397
_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^)+(0.0373P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0757
_refine_ls_wR_factor_ref         0.0788
_reflns_number_gt                3547
_reflns_number_total             5174
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401706r_si_002_2.cif
_cod_data_source_block           no182
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4028707