Synthesis of the Conformationally Constrained Tyrosine Analogues, (R)- and (S)-5-Hydroxy-2-aminoindan-2-carboxylic Acids
Francis N. Murigi; Gary S. Nichol; Eugene A. Mash; Journal of Organic Chemistry 75 (2010) 1293–1296; doi:10.1021/jo902438s

data_4025238
_publ_contact_author             'Professor Gene Mash'
_publ_contact_author_email       emash@email.arizona.edi
_publ_section_title
;
 Synthesis of the Conformationally Constrained Tyrosine Analogues, (R)-
 and (S)-5-Hydroxy-2-aminoindan-2-carboxylic Acids
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1293
_journal_page_last               1296
_journal_paper_doi               10.1021/jo902438s
_journal_volume                  75
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C10 H11 N O3, H2 O'
_chemical_formula_sum            'C10 H13 N O4'
_chemical_formula_weight         211.21
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.2810(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.1895(2)
_cell_length_b                   6.1491(2)
_cell_length_c                   11.6112(4)
_cell_measurement_reflns_used    8956
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      69.76
_cell_measurement_theta_min      6.41
_cell_volume                     492.73(3)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'ORTEP3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXTL and local programs'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device_type  'Bruker Kappa APEXII DUO CCD diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'silicon 111'
_diffrn_radiation_source         microsource
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_sigmaI/netI    0.0157
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            20019
_diffrn_reflns_theta_full        70.54
_diffrn_reflns_theta_max         70.54
_diffrn_reflns_theta_min         6.41
_exptl_absorpt_coefficient_mu    0.932
_exptl_absorpt_correction_T_max  0.9601
_exptl_absorpt_correction_T_min  0.6727
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS 2008/1; Sheldrick, 1996'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             224
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.043
_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   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     161
_refine_ls_number_reflns         1687
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0300
_refine_ls_R_factor_gt           0.0288
_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^)+(0.0377P)^2^+0.1296P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0697
_refine_ls_wR_factor_ref         0.0705
_reflns_number_gt                1637
_reflns_number_total             1687
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo902438s_si_004_2.cif
_cod_data_source_block           (S)-1
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4025238