Synthetic Progress toward Azadirachtins. 2. Enantio- and Diastereoselective Synthesis of the Right-Wing Fragment of 11-epi-Azadirachtin I.
Tan, Ceheng; Chen, Wei; Mu, Xinpeng; Chen, Qi; Gong, Jianxian; Luo, Tuoping; Yang, Zhen; Organic letters 17 (2015) 2338–2341; doi:10.1021/acs.orglett.5b00831

data_1554996
_publ_section_title
;
 Synthetic Progress toward Azadirachtins. 2. Enantio- and
 Diastereoselective Synthesis of the Right-Wing Fragment of
 11-epi-Azadirachtin I.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              2338
_journal_page_last               2341
_journal_paper_doi               10.1021/acs.orglett.5b00831
_journal_volume                  17
_journal_year                    2015
_chemical_formula_sum            'C19 H22 O7'
_chemical_formula_weight         362.37
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 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                 94.028(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.08080(10)
_cell_length_b                   23.3393(6)
_cell_length_c                   12.5225(8)
_cell_measurement_reflns_used    17185
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.30
_cell_measurement_theta_min      6.70
_cell_volume                     1772.82(13)
_computing_cell_refinement       'CrystalClear-SM Auto 2.0 r4'
_computing_data_collection       'CrystalClear-SM 2.0 r4 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Auto 2.0 r4'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Rigaku Saturn944+ CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_av_sigmaI/netI    0.0368
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            19888
_diffrn_reflns_theta_full        68.34
_diffrn_reflns_theta_max         68.34
_diffrn_reflns_theta_min         6.70
_exptl_absorpt_coefficient_mu    0.869
_exptl_absorpt_correction_T_max  0.8454
_exptl_absorpt_correction_T_min  0.8454
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.759
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       0.047(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   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3184
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.170
_refine_ls_R_factor_all          0.0864
_refine_ls_R_factor_gt           0.0782
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1366P)^2^+0.9755P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2202
_refine_ls_wR_factor_ref         0.2328
_reflns_number_gt                2633
_reflns_number_total             3184
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b00831_si_001.cif
_cod_data_source_block           z
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               1554996