Absolute Configuration of Anti-HIV-1 Agent (-)-Concentricolide: Total Synthesis of (+)-(R)-Concentricolide
Chih-Wei Chang; Rong-Jie Chein; Journal of Organic Chemistry 76 (2011) 4154–4157; doi:10.1021/jo2004132

data_4026306
_publ_section_title
;
 Absolute Configuration of Anti-HIV-1 Agent (-)-Concentricolide: Total
 Synthesis of (+)-(R)-Concentricolide
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4154
_journal_page_last               4157
_journal_paper_doi               10.1021/jo2004132
_journal_volume                  76
_journal_year                    2011
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C12 H9 Br O3'
_chemical_formula_sum            'C12 H9 Br O3'
_chemical_formula_weight         281.1
_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
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.961
_cell_length_b                   8.318
_cell_length_c                   18.806
_cell_measurement_reflns_used    7620
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      30.0595
_cell_measurement_theta_min      2.9202
_cell_volume                     1088.897
_computing_cell_refinement
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
        (compiled Aug 27 2010,11:50:40)
;
_computing_data_collection
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        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
        (compiled Aug 27 2010,11:50:40)
;
_computing_data_reduction
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        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
        (compiled Aug 27 2010,11:50:40)
;
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector_area_resol_mean 10.4875
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0979454
_diffrn_orient_matrix_UB_12      -0.0085018
_diffrn_orient_matrix_UB_13      0.0097143
_diffrn_orient_matrix_UB_21      0.0266767
_diffrn_orient_matrix_UB_22      -0.0023294
_diffrn_orient_matrix_UB_23      0.0363914
_diffrn_orient_matrix_UB_31      -0.0091001
_diffrn_orient_matrix_UB_32      0.0847847
_diffrn_orient_matrix_UB_33      0.001986
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0543
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            21050
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         30.13
_diffrn_reflns_theta_min         3.12
_exptl_absorpt_coefficient_mu    3.762
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.78771
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
        (compiled Aug 27 2010,11:50:40)
        empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.715
_exptl_crystal_description       prism
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.529
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.086
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.015(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3017
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0313
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0245P)^2^+0.3889P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.058
_refine_ls_wR_factor_ref         0.0625
_reflns_number_gt                2532
_reflns_number_total             3017
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo2004132_si_002.cif
_cod_data_source_block           12913
_cod_original_cell_volume        1088.9
_cod_database_code               4026306