Biomimetic Synthesis of ent-(-)-Azonazine and Stereochemical Reassignment of Natural Product.
Zhao, Ji-Chen; Yu, Shun-Ming; Liu, Yun; Yao, Zhu-Jun; Organic letters 15 (2013) 4300–4303; doi:10.1021/ol4015706

data_1512279
_publ_section_title
;
 Biomimetic Synthesis of ent-(-)-Azonazine and Stereochemical Reassignment
 of Natural Product.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4300
_journal_page_last               4303
_journal_paper_doi               10.1021/ol4015706
_journal_volume                  15
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25 H21 F6 N3 O5'
_chemical_formula_sum            'C25 H21 F6 N3 O5'
_chemical_formula_weight         557.45
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 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                   8.495
_cell_length_b                   14.253
_cell_length_c                   39.770
_cell_measurement_reflns_used    6376
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      63.60
_cell_measurement_theta_min      3.29
_cell_volume                     4815.321
_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      296(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0306
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            23271
_diffrn_reflns_theta_full        67.52
_diffrn_reflns_theta_max         67.52
_diffrn_reflns_theta_min         2.22
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.211
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_T_min  0.6472
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2288
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.482
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     740
_refine_ls_number_reflns         8499
_refine_ls_number_restraints     96
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0487
_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^)+(0.0905P)^2^+0.9990P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1353
_refine_ls_wR_factor_ref         0.1434
_reflns_number_gt                7468
_reflns_number_total             8499
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol4015706_si_003.cif
_cod_data_source_block           138
_cod_original_cell_volume        4815.3
_cod_database_code               1512279