Total synthesis of (+)-swainsonine and (+)-epi-swainsonine
Trajkovic, Milos; Balanac, Vesna; Ferjancic, Zorana; Saicic, Radomir Nikola; RSC Adv.  (2014) –; doi:10.1039/C4RA11978A

data_7218494
_publ_section_title
;
 Total synthesis of (+)-swainsonine and (+)-epi-swainsonine
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C4RA11978A
_journal_year                    2014
_chemical_absolute_configuration unk
_chemical_compound_source        synthetic
_chemical_formula_moiety         'C16 H21 N O5'
_chemical_formula_structural     'C16 H21 N O5'
_chemical_formula_sum            'C16 H21 N O5'
_chemical_formula_weight         307.34
_chemical_melting_point          ?
_chemical_name_common
;
        name
;
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_audit_creation_date             2013-10-21T10:56:40-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.3218(2)
_cell_length_b                   13.3020(5)
_cell_length_c                   21.7280(7)
_cell_measurement_reflns_used    4705
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      28.445
_cell_measurement_theta_min      3.74
_cell_volume                     1538.14(10)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2013)'
_computing_data_collection       'CrysAlisPro (Agilent Technologies, 2013)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2013)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXLE (H\"ubschle et al., 2011)'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      294(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 16.328
_diffrn_detector_type            'Sapphire3 (Agilent Technologies)'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Gemini S (Agilent Technologies)'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'glass fiber'
_diffrn_orient_matrix_UB_11      -0.0610234
_diffrn_orient_matrix_UB_12      0.0411687
_diffrn_orient_matrix_UB_13      -0.0143813
_diffrn_orient_matrix_UB_21      0.0460728
_diffrn_orient_matrix_UB_22      -0.0161111
_diffrn_orient_matrix_UB_23      -0.0289952
_diffrn_orient_matrix_UB_31      -0.1092739
_diffrn_orient_matrix_UB_32      -0.0297773
_diffrn_orient_matrix_UB_33      -0.0041882
_diffrn_radiation_collimation    '0.8 mm'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            12379
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.318
_diffrn_reflns_theta_min         3.203
_diffrn_source                   'fine focus sealed X-ray tube'
_diffrn_source_current           50
_diffrn_source_power             1.6
_diffrn_source_type              'Enhance (Mo) (Agilent Technologies)'
_diffrn_source_voltage           40
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.9824
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm using CrysAlisPro
 (Agilent Technologies,2013).
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_description       prism
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.64
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.127
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details
;
 Flack x determined using 1144 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.9(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         3133
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.123
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0355
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0398P)^2^+0.1523P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0828
_refine_ls_wR_factor_ref         0.0846
_reflns_number_gt                2958
_reflns_number_total             3133
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4ra11978a2.cif
_cod_data_source_block           vb-iii-462_1553_nc
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

Automatic conversion script
Id: cif_fix_values 2827 2014-09-09 07:05:25Z andrius 
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_cod_original_cell_volume        1538.15(10)
_cod_database_code               7218494
_shelx_res_checksum              93567