A Linchpin Synthesis of 6-Hydroxyceramides from Aziridine Aldehydes.
Liew, Sean K.; Kaldas, Sherif J.; Yudin, Andrei K.; Organic letters 18 (2016) 6268–6271; doi:10.1021/acs.orglett.6b03067

data_1555936
_publ_section_title
;
 A Linchpin Synthesis of 6-Hydroxyceramides from Aziridine Aldehydes.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              6268
_journal_page_last               6271
_journal_paper_doi               10.1021/acs.orglett.6b03067
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H35 N3 O6'
_chemical_formula_sum            'C27 H35 N3 O6'
_chemical_formula_weight         497.58
_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-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 92.686(1)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.1132(1)
_cell_length_b                   29.4098(7)
_cell_length_c                   8.8232(2)
_cell_measurement_reflns_used    7836
_cell_measurement_temperature    250(2)
_cell_measurement_theta_max      66.76
_cell_measurement_theta_min      3.01
_cell_volume                     1325.36(5)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2008)'
_diffrn_ambient_temperature      250(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            25634
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.420
_diffrn_reflns_theta_max         67.420
_diffrn_reflns_theta_min         3.005
_diffrn_source                   'Bruker ImuS with multi-layer optics'
_exptl_absorpt_coefficient_mu    0.723
_exptl_absorpt_correction_T_max  0.7529
_exptl_absorpt_correction_T_min  0.6645
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_description       needle
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
; 
 Flack x determined using 1835 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.06(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     351
_refine_ls_number_reflns         4689
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.744
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0422
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0659P)^2^+0.1424P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1116
_refine_ls_wR_factor_ref         0.1160
_reflns_Friedel_coverage         0.942
_reflns_Friedel_fraction_full    0.976
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                4164
_reflns_number_total             4689
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b03067_si_002.cif
_cod_data_source_block           d1542_a
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1555936
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.786
_shelx_estimated_absorpt_t_max   0.965
_shelx_res_checksum              63305
_shelx_hkl_checksum              67736