Expedient and practical synthesis of CERT-dependent ceramide trafficking inhibitor HPA-12 and its analogues.
Ďuriš, Andrej; Wiesenganger, Tomáš; Moravčíková, Daniela; Baran, Peter; Kožíšek, Jozef; Daïch, Adam; Berkeš, Dušan; Organic letters 13 (2011) 1642–1645; doi:10.1021/ol2001057

data_1502031
_publ_section_title
;
 Expedient and practical synthesis of CERT-dependent ceramide trafficking
 inhibitor HPA-12 and its analogues.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1642
_journal_page_last               1645
_journal_paper_doi               10.1021/ol2001057
_journal_volume                  13
_journal_year                    2011
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C13 H20 N O4'
_chemical_formula_sum            'C13 H20 N O4'
_chemical_formula_weight         254.30
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_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                 98.117(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.7687(3)
_cell_length_b                   6.0916(2)
_cell_length_c                   14.9497(6)
_cell_measurement_reflns_used    18522
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.2784
_cell_measurement_theta_min      3.5338
_cell_volume                     700.39(5)
_computing_cell_refinement       'CrysAlis CCD'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2010)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2010)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1998)'
_computing_publication_material  ' enCIFer (Allen et al., 2004)'
_computing_structure_refinement
'G. M. Sheldrick, Acta Cryst., A46 (2008) 112.'
_computing_structure_solution
'G. M. Sheldrick, Acta Cryst., A46 (2008) 112.'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Goniometer Xcalibur, CCD: Ruby (Gemini Mo)'
_diffrn_measurement_method
;
Rotation method data acquisition using \w and \f scans
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_sigmaI/netI    0.0098
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            28447
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         4.08
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_T_min  0.943
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             274
_exptl_crystal_size_max          0.982
_exptl_crystal_size_mid          0.442
_exptl_crystal_size_min          0.340
_refine_diff_density_max         0.730
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     161
_refine_ls_number_reflns         2854
_refine_ls_number_restraints     137
_refine_ls_restrained_S_all      1.508
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0693
_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^)+(0.1291P)^2^+0.2391P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2060
_refine_ls_wR_factor_ref         0.2115
_reflns_number_gt                2554
_reflns_number_total             2854
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol2001057_si_003.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1502031