Comprehensive Study of Okaspirodiol: Characterization, Total Synthesis, and Biosynthesis of a New Metabolite from Streptomyces
Tobias Bender; Tim Schuhmann; Jörg Magull; Stephanie Grond; Paultheo von Zezschwitz; Journal of Organic Chemistry 71 (2006) 7125–7132; doi:10.1021/jo060149e

data_4021950
_publ_section_title
;
 Comprehensive Study of Okaspirodiol: Characterization, Total Synthesis,
 and Biosynthesis of a New Metabolite from Streptomyces
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7125
_journal_page_last               7132
_journal_paper_doi               10.1021/jo060149e
_journal_volume                  71
_journal_year                    2006
_chemical_absolute_configuration ad
_chemical_formula_sum            'C17 H21 Br O5'
_chemical_formula_weight         385.25
_space_group_IT_number           20
_symmetry_space_group_name_Hall  'C 2c 2'
_symmetry_space_group_name_H-M   'C 2 2 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.4919(3)
_cell_length_b                   9.0192(3)
_cell_length_c                   49.8755(18)
_cell_measurement_temperature    100(2)
_cell_volume                     3370.1(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_sigmaI/netI    0.0235
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       52
_diffrn_reflns_limit_l_min       -52
_diffrn_reflns_number            8538
_diffrn_reflns_theta_full        54.18
_diffrn_reflns_theta_max         54.18
_diffrn_reflns_theta_min         1.77
_exptl_absorpt_coefficient_mu    3.528
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.569
_refine_diff_density_min         -0.599
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(2)
_refine_ls_extinction_coef       0.00042(4)
_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   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         1998
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0286
_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^)+(0.0147P)^2^+9.5915P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0644
_refine_ls_wR_factor_ref         0.0648
_reflns_number_gt                1958
_reflns_number_total             1998
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo060149esi20060123_011637.cif
_cod_database_code               4021950