Synergistic Ion-Binding Catalysis Demonstrated via an Enantioselective, Catalytic [2,3]-Wittig Rearrangement.
Kennedy, C. Rose; Guidera, Jennifer A.; Jacobsen, Eric N.; ACS central science 2 (2016) 416–423; doi:10.1021/acscentsci.6b00125

data_4516765
_publ_section_title
;
 Synergistic Ion-Binding Catalysis Demonstrated via an Enantioselective,
 Catalytic [2,3]-Wittig Rearrangement.
;
_journal_issue                   6
_journal_name_full               'ACS central science'
_journal_page_first              416
_journal_page_last               423
_journal_paper_doi               10.1021/acscentsci.6b00125
_journal_volume                  2
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C14 H16 O5'
_chemical_formula_weight         264.27
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.66580(10)
_cell_length_b                   13.9473(3)
_cell_length_c                   16.7395(4)
_cell_measurement_reflns_used    9792
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.5
_cell_measurement_theta_min      4.12
_cell_volume                     1322.80(5)
_computing_cell_refinement       'SAINT 8.34C (Bruker-AXS, 2014)'
_computing_data_collection       'APEX2 v2014.3.0 (Bruker-AXS, 2014)'
_computing_data_reduction        'SAINT 8.34C (Bruker-AXS, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL (Sheldrick, 2015)'
_computing_publication_material  'Bruker SHELXTL (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
;
Bruker D8 goniometer with CCD area detector  
;
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'I\mS microfocus tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_unetI/netI     0.0133
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            33137
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         66.593
_diffrn_reflns_theta_min         4.126
_exptl_absorpt_coefficient_mu    0.843
_exptl_absorpt_correction_T_max  0.8642
_exptl_absorpt_correction_T_min  0.8040
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details
;
 Flack x determined using 925 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(5)
_refine_ls_extinction_coef       0.0051(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2334
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0279
_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^)+(0.0340P)^2^+0.3498P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0701
_refine_ls_wR_factor_ref         0.0707
_reflns_Friedel_coverage         0.688
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                2280
_reflns_number_total             2334
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            oc6b00125_si_002.cif
_cod_data_source_block           CRK-IV-529
_cod_database_code               4516765
_shelx_estimated_absorpt_t_min   0.823
_shelx_estimated_absorpt_t_max   0.906
_shelxl_version_number           2014/6
_shelx_res_checksum              44654
_shelx_hkl_checksum              24875