A Failed Late-Stage Epimerization Thwarts an Approach to Ineleganolide.
Horn, Evan J.; Silverston, Joel S.; Vanderwal, Christopher D.; The Journal of organic chemistry 81 (2016) 1819–1838; doi:10.1021/acs.joc.5b02550

data_4036529
_publ_section_title
;
 A Failed Late-Stage Epimerization Thwarts an Approach to Ineleganolide.
;
_journal_issue                   5
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1819
_journal_page_last               1838
_journal_paper_doi               10.1021/acs.joc.5b02550
_journal_volume                  81
_journal_year                    2016
_chemical_formula_sum            'C11 H10 Br F3 O6 S'
_chemical_formula_weight         407.16
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 105.8816(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.8748(9)
_cell_length_b                   7.8647(4)
_cell_length_c                   10.3954(5)
_cell_measurement_reflns_used    9895
_cell_measurement_temperature    143(2)
_cell_measurement_theta_max      28.05
_cell_measurement_theta_min      2.37
_cell_volume                     1405.60(12)
_computing_cell_refinement       'Bruker SAINT 7.46a, 2007'
_computing_data_collection       'Bruker APEX2 2.2, 2007'
_computing_data_reduction        'Bruker SAINT 7.46a, 2007'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      143(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0177
_diffrn_reflns_av_unetI/netI     0.0136
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       10
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_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            15467
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         28.413
_diffrn_reflns_theta_min         2.369
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    3.134
_exptl_absorpt_correction_T_max  0.8650
_exptl_absorpt_correction_T_min  0.3336
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'Bruker SADABS 2008/1'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.924
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       irregular
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.534
_exptl_crystal_size_mid          0.288
_exptl_crystal_size_min          0.068
_refine_diff_density_max         0.513
_refine_diff_density_min         -0.349
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_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3302
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0232
_refine_ls_R_factor_gt           0.0208
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0344P)^2^+0.5242P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0549
_refine_ls_wR_factor_ref         0.0561
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3069
_reflns_number_total             3302
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b02550_si_003.cif
_cod_data_source_block           cdv13
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'none' was changed to
'?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4036529
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.285
_shelx_estimated_absorpt_t_max   0.815
_shelx_res_checksum              24586
_shelx_hkl_checksum              29087