Synthesis of unusual isoxazoline containingβandγ-dipeptides as potential glutamate receptor ligands
Tamborini, Lucia; Mastronardi, Federica; Dall'Oglio, Federica; De Micheli, Carlo; Nielsen, Birgitte; Lo Presti, Leonardo; Conti, Paola; Pinto, Andrea; Med. Chem. Commun. 6 (2015) 1260–; doi:10.1039/C5MD00159E

data_7117187
_publ_section_title
;
 Synthesis of unusual isoxazoline containing\band\g-dipeptides as
 potential glutamate receptor ligands
;
_journal_issue                   7
_journal_name_full               'Med. Chem. Commun.'
_journal_page_first              1260
_journal_paper_doi               10.1039/C5MD00159E
_journal_volume                  6
_journal_year                    2015
_chemical_absolute_configuration syn
_chemical_formula_moiety         '(C11 H14 N3 O6)','H2O'
_chemical_formula_sum            'C11 H16 N3 O7'
_chemical_formula_weight         302.27
_chemical_name_systematic
'(3aR,6aS)-5-((S)-4-amino-4-carboxybutanoyl)-4,5,6,6a-tetrahydro-3aH-pyrrolo[3,4-d]isoxazole-3-carboxylic acid'
_chemical_temperature_decomposition_gt 353
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.4
_audit_creation_date             2015-04-16
_audit_creation_method           SHELXL-2014/4
_audit_update_record
;
2015-04-16 deposited with the CCDC.
2015-05-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.4380(7)
_cell_length_b                   10.4231(15)
_cell_length_c                   22.933(3)
_cell_measurement_reflns_used    341
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      13.333
_cell_measurement_theta_min      3.851
_cell_volume                     1299.9(3)
_computing_cell_refinement
'SAINT+ (Bruker AXS, Madison (USA) 1994-1996)'
_computing_data_collection
'SAINT+ (Bruker AXS, Madison (USA) 1994-1996)'
_computing_data_reduction
'SAINT+ (Bruker AXS, Madison (USA) 1994-1996)'
_computing_molecular_graphics
'DIAMOND v3.2i (Brandenburg, Bonn (Germany) 1997-2012)'
_computing_structure_refinement  'SHELXL-2014/4 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2013   (Sheldrick, 2013)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker AXS Smart Apex II'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1137
_diffrn_reflns_av_unetI/netI     0.0952
_diffrn_reflns_laue_measured_fraction_full 1.000
_diffrn_reflns_laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            19388
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.492
_diffrn_reflns_theta_min         1.776
_diffrn_source                   'sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8953
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Sadabs (Bruker, 2008/1)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_description       Plate
_exptl_crystal_F_000             636
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_exptl_crystal_size_max          0.225
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.025
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 483 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.6(10)
_refine_ls_extinction_coef       0.013(2)
_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   1.005
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         2982
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.1337
_refine_ls_R_factor_gt           0.0496
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0346P)^2^+0.0178P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0769
_refine_ls_wR_factor_ref         0.0990
_reflns_Friedel_coverage         0.697
_reflns_friedel_fraction_full    1.000
_reflns_friedel_fraction_max     1.000
_reflns_number_gt                1573
_reflns_number_total             2982
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5md00159e1.cif
_cod_data_source_block           FM104
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' tag was changed to
'_chemical_temperature_decomposition_gt' since the value was
specified 'more than' ('>') a certain temperature. The value '> 353
(decomposition)' was changed to '353' - it should be numeric and
without a unit designator.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 7117187.cif.
;
_cod_database_code               7117187
_shelx_res_checksum              17670