Synthesis and biological evaluation of (-)-kainic acid analogues as phospholipase D-coupled metabotropic glutamate receptor ligands.
Zanato, Chiara; Watson, Sonia; Bewick, Guy S.; Harrison, William T. A.; Zanda, Matteo; Organic & biomolecular chemistry 12 (2014) 9638–9643; doi:10.1039/c4ob02002b

data_7154144
_publ_section_title
;
 Synthesis and biological evaluation of (-)-kainic acid analogues as
 phospholipase D-coupled metabotropic glutamate receptor ligands.
;
_journal_issue                   47
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9638
_journal_page_last               9643
_journal_paper_doi               10.1039/c4ob02002b
_journal_volume                  12
_journal_year                    2014
_chemical_formula_moiety         'C33 H33 N O5'
_chemical_formula_sum            'C33 H33 N O5'
_chemical_formula_weight         523.60
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.012(2)
_cell_length_b                   13.289(3)
_cell_length_c                   18.958(4)
_cell_measurement_reflns_used    3452
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.6
_cell_measurement_theta_min      21.5
_cell_volume                     2774.3(10)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_sigmaI/netI    0.0196
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            29043
_diffrn_reflns_theta_full        68.87
_diffrn_reflns_theta_max         68.87
_diffrn_reflns_theta_min         4.06
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.675
_exptl_absorpt_correction_T_max  0.9543
_exptl_absorpt_correction_T_min  0.8232
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1112
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Methanol'
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(11)
_refine_ls_extinction_coef       0.00072(14)
_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   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     360
_refine_ls_number_reflns         5098
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0251
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0330P)^2^+0.5895P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0638
_refine_ls_wR_factor_ref         0.0644
_reflns_number_gt                4994
_reflns_number_total             5098
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            c4ob02002b2.cif
_cod_data_source_block           zcz
_cod_depositor_comments          'Adding full bibliography for 7154144.cif.'
_cod_database_code               7154144