Biomimetic Desymmetrization of a Carboxylic Acid
Knowe, Matthew T.; Danneman, Michael W.; Sun, Sarah; Pink, Maren; Johnston, Jeffrey N.; Journal of the American Chemical Society  (2018) –; doi:10.1021/jacs.7b12185

data_4127167
_publ_section_title
;
 Biomimetic Desymmetrization of a Carboxylic Acid
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.7b12185
_journal_year                    2018
_chemical_formula_moiety         'C12 H11 I O2'
_chemical_formula_sum            'C12 H11 I O2'
_chemical_formula_weight         314.11
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 103.702(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.2856(8)
_cell_length_b                   6.1896(4)
_cell_length_c                   15.4428(11)
_cell_measurement_reflns_used    9859
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.01
_cell_measurement_theta_min      2.42
_cell_volume                     1140.90(13)
_computing_cell_refinement       'APEX II v2014.11-0 (Bruker, 2014)'
_computing_data_collection       'APEX II v2014.11-0 (Bruker, 2014)'
_computing_data_reduction        'APEX II v2014.11-0 (Bruker, 2014)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2013)'
_computing_publication_material  'SHELXTL (Bruker, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELX (Bruker, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 83.33
_diffrn_detector_type            'Bruker APEXII'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
'0.50 degree frames measured for 20 seconds each'
_diffrn_measurement_device       'APEX Kappa Duo'
_diffrn_measurement_device_type  Kappa
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            26319
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.130
_diffrn_reflns_theta_min         1.357
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    2.784
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5707
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, G. Sheldrick; 2014'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.829
_exptl_crystal_description       plate
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.638
_refine_diff_density_min         -0.833
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details
;
 Flack x determined using 2441 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.002(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         6227
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0201
_refine_ls_R_factor_gt           0.0186
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0198P)^2^+0.2503P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0427
_refine_ls_wR_factor_ref         0.0434
_reflns_Friedel_coverage         0.708
_reflns_Friedel_fraction_full    0.939
_reflns_Friedel_fraction_max     0.838
_reflns_number_gt                5978
_reflns_number_total             6227
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b12185_si_004.cif
_cod_data_source_block           16042
_cod_original_cell_volume        1140.89(13)
_cod_database_code               4127167
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.479
_shelx_estimated_absorpt_t_max   0.873
_shelx_res_checksum              3335
_shelx_hkl_checksum              46453