Stereoselective Synthesis of 3-Aminoindan-1-ones and Subsequent Incorporation into HIV-1 Protease Inhibitors
Anna Arefalk; Johan Wannberg; Mats Larhed; Anders Hallberg; Journal of Organic Chemistry 71 (2006) 1265–1268; doi:10.1021/jo0521504

data_4021449
_publ_contact_author_name        'Dr S.V. Belyakov'
_publ_section_title
;
 Stereoselective Synthesis of 3-Aminoindan-1-ones and Subsequent
 Incorporation into HIV-1 Protease Inhibitors
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1265
_journal_page_last               1268
_journal_paper_doi               10.1021/jo0521504
_journal_volume                  71
_journal_year                    2006
_chemical_absolute_configuration rm
_chemical_compound_source        'synthesised by authors'
_chemical_formula_moiety         'C13 H17 N O2 S '
_chemical_formula_sum            'C13 H17 N O2 S'
_chemical_formula_weight         251.348
_chemical_name_systematic
; 
3-t-Butylsulfinamyl-1-indanone 
;
_space_group_IT_number           144
_space_group_name_Hall           'P 31'
_space_group_name_H-M_alt        'P 31'
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  'P 31'
_symmetry_space_group_name_H-M   'P 31'
_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                120.00
_cell_formula_units_Z            3
_cell_length_a                   11.080(2)
_cell_length_b                   11.080(1)
_cell_length_c                   9.6707(11)
_cell_measurement_reflns_used    2171
_cell_measurement_temperature    293(1)
_cell_measurement_theta_max      27.103
_cell_measurement_theta_min      0.998
_cell_volume                     1028.2(2)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'KappaCCD (Nonius, 1999)'
_computing_data_reduction        'Denzo and Scalepak (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEP-II (Johnson, 1976)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_measured_fraction_theta_full 0.949
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_method       CCD
_diffrn_orient_matrix_type       X=UH
_diffrn_orient_matrix_UB_11      0.03932
_diffrn_orient_matrix_UB_12      -0.01709
_diffrn_orient_matrix_UB_13      -0.02958
_diffrn_orient_matrix_UB_21      0.04468
_diffrn_orient_matrix_UB_22      -0.02555
_diffrn_orient_matrix_UB_23      0.07415
_diffrn_orient_matrix_UB_31      -0.04468
_diffrn_orient_matrix_UB_32      -0.09311
_diffrn_orient_matrix_UB_33      -0.00515
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           ' MoK\a'
_diffrn_radiation_wavelength_id  all
_diffrn_reflns_av_R_equivalents  0.0933
_diffrn_reflns_av_sigmaI/netI    0.1234
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4063
_diffrn_reflns_theta_full        27.10
_diffrn_reflns_theta_max         27.10
_diffrn_reflns_theta_min         5.60
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.909
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             402
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2702
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.1411
_refine_ls_R_factor_gt           0.0961
_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^)+(0.0380P)^2^+1.6100P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1897
_refine_ls_wR_factor_ref         0.2158
_reflns_number_gt                1894
_reflns_number_total             2709
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0521504si20051014_074442.cif
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Trigonal' changed to 'trigonal' according
to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_formula_sum        'C13 H17 N O2 S '
_cod_database_code               4021449