A Potential Route to Neuroprostanes and Isoprostanes: Preparation of the Four Enantiomerically Pure Diastereomers of 13-F~4t~-NeuroP
Douglass F. Taber; P. Ganapati Reddy; Kyle O. Arneson; Journal of Organic Chemistry 73 (2008) 3467–3474; doi:10.1021/jo702600v

data_4023375
_publ_section_title
;
 A Potential Route to Neuroprostanes and Isoprostanes: Preparation
 of the Four Enantiomerically Pure Diastereomers of 13-F~4t~-NeuroP
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3467
_journal_page_last               3474
_journal_paper_doi               10.1021/jo702600v
_journal_volume                  73
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_sum            'C36 H31 Br3 O8'
_chemical_formula_weight         831.34
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_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(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   73.380(8)
_cell_length_b                   5.931(2)
_cell_length_c                   7.879(4)
_cell_measurement_reflns_used    953
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.15
_cell_measurement_theta_min      2.81
_cell_volume                     3429(2)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2001)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker AXS APEX diffractometer'
_diffrn_measurement_method       \w
_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  0.0463
_diffrn_reflns_av_sigmaI/netI    0.0530
_diffrn_reflns_limit_h_max       86
_diffrn_reflns_limit_h_min       -86
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            16320
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.67
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.580
_exptl_absorpt_correction_T_max  0.9158
_exptl_absorpt_correction_T_min  0.4829
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.610
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.575
_refine_diff_density_min         -0.517
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881, Friedel pairs=3380'
_refine_ls_abs_structure_Flack   0.015(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     425
_refine_ls_number_reflns         6003
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0419
_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^)+(0.0459P)^2^+9.7491P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1018
_refine_ls_wR_factor_ref         0.1046
_reflns_number_gt                5631
_reflns_number_total             6003
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo702600v-File001.cif
_cod_data_source_block           dout021a
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_sg_symbol_H-M      'C 2'
_cod_database_code               4023375