Synthesis of Hydroxylated Bicyclic Amino Acids from L-Tyrosine: Octahydro-1H-indole Carboxylates
Joshua G. Pierce; Dhanalakshmi Kasi; Makoto Fushimi; Anthony Cuzzupe; Peter Wipf; Journal of Organic Chemistry 73 (2008) 7807–7810; doi:10.1021/jo801552j

data_4023721
_publ_section_title
;
 Synthesis of Hydroxylated Bicyclic Amino Acids from
 L-Tyrosine: Octahydro-1H-indole Carboxylates
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7807
_journal_page_last               7810
_journal_paper_doi               10.1021/jo801552j
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C17 H20 Br N O7'
_chemical_formula_weight         430.25
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 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            8
_cell_length_a                   16.5665(14)
_cell_length_b                   5.8536(5)
_cell_length_c                   35.113(3)
_cell_measurement_reflns_used    4284
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.80
_cell_measurement_theta_min      2.32
_cell_volume                     3405.1(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0628
_diffrn_reflns_av_sigmaI/netI    0.0705
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       53
_diffrn_reflns_limit_l_min       -51
_diffrn_reflns_number            41660
_diffrn_reflns_theta_full        32.59
_diffrn_reflns_theta_max         32.59
_diffrn_reflns_theta_min         2.32
_exptl_absorpt_coefficient_mu    2.456
_exptl_absorpt_correction_T_max  0.6140
_exptl_absorpt_correction_T_min  0.4554
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.679
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1760
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.22
_refine_diff_density_max         1.661
_refine_diff_density_min         -0.582
_refine_diff_density_rms         0.121
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.023(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     470
_refine_ls_number_reflns         11941
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.992
_refine_ls_R_factor_all          0.0984
_refine_ls_R_factor_gt           0.0571
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0665P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1193
_refine_ls_wR_factor_ref         0.1386
_reflns_number_gt                7815
_reflns_number_total             11941
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo801552j_si_002.cif
_cod_data_source_block           mf468
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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_database_code               4023721