Total Syntheses of (+)-α-Allokainic Acid and (-)-2- epi-α-Allokainic Acid Employing Ketopinic Amide as a Chiral Auxiliary.
Liang, Yu-Fu; Chung, Chuang-Chung; Liao, De-Jhong; Lee, Woo-Jer; Tu, Yu-Wei; Uang, Biing-Jiun; The Journal of organic chemistry 83 (2018) 10564–10572; doi:10.1021/acs.joc.8b01383

data_4035092
_publ_section_title
;
 Total Syntheses of (+)-\a-Allokainic Acid and (-)-2- epi-\a-Allokainic
 Acid Employing Ketopinic Amide as a Chiral Auxiliary.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10564
_journal_page_last               10572
_journal_paper_doi               10.1021/acs.joc.8b01383
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration rm
_chemical_formula_sum            'C10 H17 N O5'
_chemical_formula_weight         231.24
_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'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 91.597(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.9760(2)
_cell_length_b                   9.0579(4)
_cell_length_c                   10.1215(4)
_cell_measurement_reflns_used    3609
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.5436
_cell_measurement_theta_min      4.3699
_cell_volume                     547.66(4)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.958
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0169
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.958
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3775
_diffrn_reflns_point_group_measured_fraction_full 0.906
_diffrn_reflns_point_group_measured_fraction_max 0.925
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.539
_diffrn_reflns_theta_min         4.370
_exptl_absorpt_coefficient_mu    0.951
_exptl_absorpt_correction_T_max  0.9492
_exptl_absorpt_correction_T_min  0.8557
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Lump
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 770 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.12(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1785
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0238
_refine_ls_R_factor_gt           0.0238
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0347P)^2^+0.1140P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0627
_refine_ls_wR_factor_ref         0.0627
_reflns_Friedel_coverage         0.769
_reflns_Friedel_fraction_full    0.846
_reflns_Friedel_fraction_max     0.864
_reflns_number_gt                1780
_reflns_number_total             1785
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01383_si_001.cif
_cod_data_source_block           cu_150525lt_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' 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'
_cod_database_code               4035092
_shelxl_version_number           2014/6
_shelx_res_checksum              8977
_shelx_hkl_checksum              41424