Enantioselective total synthesis of the highly selective sphingosine-1-receptor VPC01091 by the Heck desymmetrization of a non-activated cyclopentene-fused spiro-pyrrolidinone.
Khan, Ismat Ullah; Kattela, Shivashankar; Hassan, Abbas; Correia, Carlos Roque Duarte; Organic & biomolecular chemistry 14 (2016) 9476–9480; doi:10.1039/c6ob01892k

data_7155286
_publ_section_title
;
 Enantioselective total synthesis of the highly selective
 sphingosine-1-receptor VPC01091 by the Heck desymmetrization of a
 non-activated cyclopentene-fused spiro-pyrrolidinone.
;
_journal_issue                   40
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9476
_journal_page_last               9480
_journal_paper_doi               10.1039/c6ob01892k
_journal_volume                  14
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H23 N O5'
_chemical_formula_sum            'C19 H23 N O5'
_chemical_formula_weight         345.38
_chemical_name_systematic        K071
_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
_audit_update_record
;
2016-08-04 deposited with the CCDC.
2016-09-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.5840(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.0073(4)
_cell_length_b                   5.9225(2)
_cell_length_c                   13.6415(4)
_cell_measurement_reflns_used    114
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      38.0
_cell_measurement_theta_min      9.57
_cell_volume                     913.97(5)
_computing_cell_refinement       '<i>SAINT</i> (Bruker, 2010)'
_computing_data_collection       '<i>APEX2</i> (Bruker, 2010)'
_computing_data_reduction        '<i>SAINT</i> (Bruker, 2010)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX CCD detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.0134
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            30012
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.136
_diffrn_reflns_theta_min         3.439
_exptl_absorpt_coefficient_mu    0.748
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_T_min  0.6730
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2010)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.319
_exptl_crystal_size_mid          0.315
_exptl_crystal_size_min          0.132
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details
;
 Flack x determined using 1404 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(2)
_refine_ls_extinction_coef       0.054(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         3241
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0402
_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^)+(0.0626P)^2^+0.0854P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0980
_refine_ls_wR_factor_ref         0.0981
_reflns_Friedel_coverage         0.777
_reflns_Friedel_fraction_full    0.959
_reflns_Friedel_fraction_max     0.953
_reflns_number_gt                3228
_reflns_number_total             3241
_reflns_threshold_expression     'I > 2\s(I)'
_publcif_datablock.id            {3c7bc3d3-bf32-4ef7-81ec-d1f3487c47a4}
_cod_data_source_file            c6ob01892k2.cif
_cod_data_source_block           Ko_71
_cod_depositor_comments          'Adding full bibliography for 7155286.cif.'
_cod_database_code               7155286
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.796
_shelx_estimated_absorpt_t_max   0.908
_shelx_res_checksum              33897