Synthesis of the bridging framework of phragmalin-type limonoids.
Lebold, Terry P.; Gallego, Gary M.; Marth, Christopher J.; Sarpong, Richmond; Organic letters 14 (2012) 2110–2113; doi:10.1021/ol300647k

data_1507619
_publ_section_title
;
 Synthesis of the bridging framework of phragmalin-type limonoids.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              2110
_journal_page_last               2113
_journal_paper_doi               10.1021/ol300647k
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C19 H19 Br O5'
_chemical_formula_weight         407.25
_chemical_name_common            TL5-mullet
_chemical_name_systematic
;
 sarpong25
;
_space_group.centring_type       P
_space_group_IT_number           2
_space_group.IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                118.274(2)
_cell_angle_beta                 101.488(2)
_cell_angle_gamma                102.795(2)
_cell_formula_units_Z            4
_cell_length_a                   11.8721(11)
_cell_length_b                   13.2210(12)
_cell_length_c                   13.4918(12)
_cell_measurement_reflns_used    9846
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.90
_cell_measurement_theta_min      3.98
_cell_volume                     1700.9(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX
_computing_structure_refinement  SHELXL-97
_computing_structure_solution    SIR-2008
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'HELIOS multilayer mirrors'
_diffrn_radiation_source         'microfocus rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_sigmaI/netI    0.0136
_diffrn_refln_scan_rate          5
_diffrn_refln_scan_width         1.0
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            33120
_diffrn_reflns_theta_full        67.00
_diffrn_reflns_theta_max         68.24
_diffrn_reflns_theta_min         3.86
_exptl_absorpt_coefficient_mu    3.537
_exptl_absorpt_correction_T_max  0.8715
_exptl_absorpt_correction_T_min  0.7651
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.590
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.319
_refine_diff_density_min         -0.952
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     453
_refine_ls_number_reflns         6052
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0340
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0439P)^2^+2.5994P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0875
_refine_ls_wR_factor_ref         0.0878
_reflns_number_gt                5973
_reflns_number_total             6052
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol300647k_si_001.cif
_cod_data_source_block           sarpong25
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_space_group.centring_type' value 'primitive' was replaced with the
value 'P' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5642 2017-10-24 12:04:52Z antanas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1507619