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_4025237
_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         'C29 H30 Br N3 O4 S'
_chemical_formula_sum            'C29 H30 Br N3 O4 S'
_chemical_formula_weight         596.53
_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                   10.2029(2)
_cell_length_b                   10.3818(2)
_cell_length_c                   25.7025(4)
_cell_measurement_reflns_used    9979
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.25
_cell_measurement_theta_min      3.44
_cell_volume                     2722.52(9)
_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      100(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker Kappa APEXII DUO CCD diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         microsource
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0567
_diffrn_reflns_av_sigmaI/netI    0.0382
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            27800
_diffrn_reflns_theta_full        69.48
_diffrn_reflns_theta_max         69.48
_diffrn_reflns_theta_min         3.44
_exptl_absorpt_coefficient_mu    3.105
_exptl_absorpt_correction_T_max  0.7761
_exptl_absorpt_correction_T_min  0.3520
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS 2008/1; Sheldrick, 1996'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.835
_refine_diff_density_min         -0.609
_refine_diff_density_rms         0.082
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.196
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     354
_refine_ls_number_reflns         5021
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.196
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0433
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0360P)^2^+4.1848P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1011
_refine_ls_wR_factor_ref         0.1024
_reflns_number_gt                4781
_reflns_number_total             5021
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo902438s_si_004_1.cif
_cod_data_source_block           (R,S)-8
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to the built-in table from CIF Core
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4025237