Revision of the Structure of N, O-Diacetylsolasodine. Unusual Epimerization at the Spiro Carbon Atom during Acetylation of Solasodine.
Czajkowska-Szczykowska, Dorota; Jastrzebska, Izabella; Rode, Joanna E.; Morzycki, Jacek W.; Journal of natural products 82 (2019) 59–65; doi:10.1021/acs.jnatprod.8b00573

data_1552599
_publ_section_title
;
 Revision of the Structure of N, O-Diacetylsolasodine. Unusual
 Epimerization at the Spiro Carbon Atom during Acetylation of Solasodine.
;
_journal_issue                   1
_journal_name_full               'Journal of natural products'
_journal_page_first              59
_journal_page_last               65
_journal_paper_doi               10.1021/acs.jnatprod.8b00573
_journal_volume                  82
_journal_year                    2019
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C31 H47 N O4'
_chemical_formula_sum            'C31 H47 N O4'
_chemical_formula_weight         497.69
_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   geom
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 99.0080(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.12930(10)
_cell_length_b                   7.38680(10)
_cell_length_c                   18.5718(2)
_cell_measurement_reflns_used    10267
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.5140
_cell_measurement_theta_min      4.4070
_cell_volume                     1372.46(3)
_computing_cell_refinement       'CrysAlis PRO (Agilent Technologies, 2011)'
_computing_data_collection       'CrysAlis PRO (Agilent Technologies, 2011)'
_computing_data_reduction        'CrysAlis PRO (Agilent Technologies, 2011)'
_computing_molecular_graphics    'OLEX2 (Dolomanov <i>et al.</i>, 2009)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXD-2016(Sheldrick, 2016)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4052
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -89.00  86.00   1.00    1.00    --    0.00 -17.00 127.00  175
  2  \w    -30.00 145.00   1.00    1.00    --   59.00 -17.00 127.00  175
  3  \w     32.00 178.00   1.00    1.00    --  118.00  17.00 -63.00  146
  4  \w     29.00 178.00   1.00    1.00    --  118.00 -17.00 127.00  149
  5  \w    -86.00  89.00   1.00    1.00    --    0.00  17.00 -63.00  175
  6  \w      1.00  47.00   1.00    1.00    --    0.00 -99.00-180.00   46
  7  \w   -145.00  30.00   1.00    1.00    --  -59.00  17.00 -63.00  175
  8  \w    -96.00  -2.00   1.00    1.00    --  -59.00 125.00 -30.00   94
  9  \w     94.00 143.00   1.00    1.00    --   59.00 125.00-150.00   49
 10  \w     94.00 143.00   1.00    1.00    --   59.00 125.00  90.00   49
 11  \w     94.00 143.00   1.00    1.00    --   59.00 125.00-180.00   49
 12  \w     32.00 116.00   1.00    1.00    --  118.00-111.00  60.00   84
 13  \w     32.00 116.00   1.00    1.00    --  118.00-111.00  90.00   84
 14  \w     32.00 116.00   1.00    1.00    --  118.00-111.00 120.00   84
 15  \w     32.00 155.00   1.00    1.00    --  118.00 -64.00 -90.00  123
 16  \w     27.00 162.00   1.00    1.00    --  118.00 -92.00 -60.00  135
 17  \w    100.00 178.00   1.00    1.00    --  118.00 111.00 120.00   78
 18  \w     32.00 116.00   1.00    1.00    --  118.00-111.00 150.00   84
 19  \w     82.00 178.00   1.00    1.00    --  118.00  50.00-150.00   96
 20  \w     34.00 134.00   1.00    1.00    --  118.00 -38.00 -90.00  100
 21  \w     82.00 126.00   1.00    1.00    --  118.00  64.00  30.00   44
 22  \w    134.00 160.00   1.00    1.00    --  118.00  64.00  30.00   26
 23  \w     35.00  72.00   1.00    1.00    --  118.00-125.00 -16.43   37
 24  \w     77.00 119.00   1.00    1.00    --  118.00-125.00 -16.43   42
 25  \w    129.00 162.00   1.00    1.00    --  118.00 -25.00 -90.00   33
 26  \w     55.00  99.00   1.00    1.00    --  118.00 -25.00 -90.00   44
 27  \w     28.00 101.00   1.00    1.00    --  118.00 -12.00 -90.00   73
 28  \w    146.00 178.00   1.00    1.00    --  118.00 -12.00 -90.00   32
 29  \w     55.00  85.00   1.00    1.00    --  118.00-111.00-120.00   30
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1389512000
_diffrn_orient_matrix_UB_12      -0.0389666000
_diffrn_orient_matrix_UB_13      -0.0442224000
_diffrn_orient_matrix_UB_21      0.0639046000
_diffrn_orient_matrix_UB_22      -0.0243762000
_diffrn_orient_matrix_UB_23      -0.0694555000
_diffrn_orient_matrix_UB_31      0.0189189000
_diffrn_orient_matrix_UB_32      -0.2031765000
_diffrn_orient_matrix_UB_33      0.0167119000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            15501
_diffrn_reflns_point_group_measured_fraction_full 0.743
_diffrn_reflns_point_group_measured_fraction_max 0.731
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.542
_diffrn_reflns_theta_min         4.419
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.613
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.15e (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_description       needle
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.516
_exptl_crystal_size_mid          0.042
_exptl_crystal_size_min          0.038
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         4236
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0326
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0505P)^2^+0.2494P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0834
_refine_ls_wR_factor_ref         0.0852
_reflns_Friedel_coverage         0.0
_reflns_number_gt                4111
_reflns_number_total             4236
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np8b00573_si_002.cif
_cod_data_source_block           IZA_54_P
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1552599
_shelx_shelxl_version_number     2016/6
_shelx_res_checksum              9981
_shelx_hkl_checksum              6822