Synthesis of Two Unnatural Oxygenated Aaptaminoids
Giorgio Abbiati; Arjana Doda; Monica Dell'Acqua; Valentina Pirovano; Diego Facoetti; Silvia Rizzato; Elisabetta Rossi; Journal of Organic Chemistry 77 (2012) 10461–10467; doi:10.1021/jo3020598

data_4027737
_publ_contact_author_address
;     
 Universita' degli Studi di Milano, Dipartimento di Scienze Farmaceutiche, 
 Sezione di Chimica Generale e Organica A. Marchesini,
 via Venezian, 21, 20133 Milano, Italy
;
_publ_contact_author_email       giorgio.abbiati@unimi.it
_publ_contact_author_name        'Giorgio Abbiati'
_publ_section_title
;
 Synthesis of Two Unnatural Oxygenated Aaptaminoids
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10461
_journal_page_last               10467
_journal_paper_doi               10.1021/jo3020598
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C16 H19 N O3 Si'
_chemical_formula_sum            'C16 H19 N O3 Si'
_chemical_formula_weight         301.41
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_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           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 99.891(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.872(3)
_cell_length_b                   7.111(2)
_cell_length_c                   19.434(5)
_cell_measurement_reflns_used    887
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      17.44
_cell_measurement_theta_min      2.19
_cell_volume                     1616.3(7)
_computing_molecular_graphics
'ORTEP-3: Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565'
_computing_publication_material
'WinGX: Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 CCD_plate
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device       SMART
_diffrn_measurement_method       omega-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1057
_diffrn_reflns_av_unetI/netI     0.0709
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            17800
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         25.24
_diffrn_reflns_theta_min         1.88
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.154
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.6481
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Sadabs 2.01 (Bruker AXS, 1999)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_description       needle
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2932
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.1417
_refine_ls_R_factor_gt           0.0648
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0844P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.156
_refine_ls_wR_factor_ref         0.1917
_reflns_number_gt                1465
_reflns_number_total             2932
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo3020598_si_002.cif
_cod_data_source_block           11
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4027737