Development of a Concise Synthesis of (+)-Ingenol.
McKerrall, Steven J.; Jørgensen, Lars; Kuttruff, Christian A.; Ungeheuer, Felix; Baran, Phil S.; Journal of the American Chemical Society 136 (2014) 5799–; doi:10.1021/ja501881p

data_4121664
_publ_section_title
;
 Development of a Concise Synthesis of (+)-Ingenol.
;
_journal_issue                   15
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5799
_journal_paper_doi               10.1021/ja501881p
_journal_volume                  136
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C30 H33 Br O8, C5 H12'
_chemical_formula_sum            'C35 H45 Br O8'
_chemical_formula_weight         673.62
_space_group_crystal_system      trigonal
_space_group_IT_number           144
_space_group_name_Hall           'P 31'
_space_group_name_H-M_alt        'P 31'
_symmetry_space_group_name_Hall  'P 31'
_symmetry_space_group_name_H-M   'P 31'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2012
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            3
_cell_length_a                   13.9788(5)
_cell_length_b                   13.9788(5)
_cell_length_c                   14.9179(6)
_cell_measurement_reflns_used    9664
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.39
_cell_measurement_theta_min      3.65
_cell_volume                     2524.52(16)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean '512 x 512'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            22635
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        68.000
_diffrn_reflns_theta_max         68.384
_diffrn_reflns_theta_min         3.651
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    2.069
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6372
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_meas      ?
_exptl_crystal_description       Needle
_exptl_crystal_F_000             1062
_exptl_crystal_size_max          0.081
_exptl_crystal_size_mid          0.015
_exptl_crystal_size_min          0.005
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
; 
 Flack x determined using 2551 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.004(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     405
_refine_ls_number_reflns         5974
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0319
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
; 
 w=1/[\s^2^(Fo^2^)+(0.0276P)^2^+0.7084P] 
 where P=(Fo^2^+2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0749
_refine_ls_wR_factor_ref         0.0765
_reflns_Friedel_coverage         0.942
_reflns_Friedel_fraction_full    0.945
_reflns_Friedel_fraction_max     0.935
_reflns_number_gt                5577
_reflns_number_total             5974
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja501881p_si_003.cif
_cod_data_source_block           baran276
_cod_depositor_comments
;Adding full bibliography for 4121658--4121664.cif.

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        2524.5(2)
_cod_database_code               4121664
_shelx_estimated_absorpt_t_min   0.850
_shelx_estimated_absorpt_t_max   0.990
_shelxl_version_number           2012-9
_shelx_res_checksum              66186
_shelx_hkl_checksum              14483