Generation of Anti-trypanosomal Agents through Concise Synthesis and Structural Diversification of Sesquiterpene Analogues
Hiroki Oguri; Takahisa Hiruma; Yutaka Yamagishi; Hideaki Oikawa; Aki Ishiyama; Kazuhiko Otoguro; Haruki Yamada; Satoshi Ōmura; Journal of the American Chemical Society 133 (2011) 7096–7105; doi:10.1021/ja200374q

data_4106105
_publ_section_title
;
 Generation of Anti-trypanosomal Agents through Concise Synthesis and
 Structural Diversification of Sesquiterpene Analogues
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7096
_journal_page_last               7105
_journal_paper_doi               10.1021/ja200374q
_journal_volume                  133
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H20 N2 O2'
_chemical_formula_sum            'C15 H20 N2 O2'
_chemical_formula_weight         260.33
_chemical_name_systematic
;
(1S,4aS,8R,8aS)-8-hydroxy-4'-methyl-3,4,4a,5,6,7,8,8a-
octahydro-2H-spiro[naphthalene-1,6'-[1,2]oxazine]-4a-carbonitrile
;
_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            4
_cell_length_a                   8.15817(15)
_cell_length_b                   12.4378(2)
_cell_length_c                   13.4449(3)
_cell_measurement_reflns_used    15758
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.25
_cell_measurement_theta_min      4.84
_cell_volume                     1364.25(5)
_computing_cell_refinement       'Rigaku RAPID AUTO'
_computing_data_collection       'Rigaku RAPID AUTO'
_computing_data_reduction        'Rigaku RAPID AUTO'
_computing_molecular_graphics    'Crystal Structure and PLATON(Spek, 2003)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'IP area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0211
_diffrn_reflns_av_sigmaI/netI    0.0156
_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       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15758
_diffrn_reflns_theta_full        68.25
_diffrn_reflns_theta_max         68.25
_diffrn_reflns_theta_min         4.84
_exptl_absorpt_coefficient_mu    0.679
_exptl_absorpt_correction_T_max  0.9799
_exptl_absorpt_correction_T_min  0.9109
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Lorentz and polarization'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.127
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2479
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.126
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0317
_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^)+(0.0286P)^2^+0.3045P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0719
_refine_ls_wR_factor_ref         0.0778
_reflns_number_gt                2251
_reflns_number_total             2479
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja200374q_si_003.cif
_cod_data_source_block           shelxl
_cod_original_cell_volume        1364.25(4)
_cod_database_code               4106105