The synthesis of solasodine F-homo-analogues.
Kiełczewska, Urszula; Morzycki, Jacek W.; Rárová, Lucie; Wojtkielewicz, Agnieszka; Organic & biomolecular chemistry 17 (2019) 9050–9058; doi:10.1039/c9ob01888c

data_7157120
_publ_section_title
;
 The synthesis of solasodine F-homo-analogues.
;
_journal_issue                   40
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9050
_journal_page_last               9058
_journal_paper_doi               10.1039/c9ob01888c
_journal_volume                  17
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C36 H49 N O6 S'
_chemical_formula_sum            'C36 H49 N O6 S'
_chemical_formula_weight         623.82
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-03-07
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2019-03-08 deposited with the CCDC.    2019-09-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.6151(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.41147(5)
_cell_length_b                   9.65864(5)
_cell_length_c                   26.39665(13)
_cell_measurement_reflns_used    41677
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.5210
_cell_measurement_theta_min      3.3020
_cell_volume                     1633.992(17)
_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 0.993
_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    -81.00  26.00   1.00    1.00    --  -41.32  94.00 -30.00  107
  2  \w     -4.00  81.00   1.00    1.00    --   41.32 -94.00-140.00   85
  3  \w     29.00 109.00   1.00    1.00    --  113.00 -94.00-140.00   80
  4  \w    101.00 178.00   1.00    1.00    --  113.00  94.00 -30.00   77
  5  \w   -124.00 -79.00   1.00    1.00    --  -41.32 -99.00   0.00   45
  6  \w   -117.00 -15.00   1.00    1.00    --  -41.32 -38.00  30.00  102
  7  \w     23.00  99.00   1.00    1.00    --   41.32-125.00 120.00   76
  8  \w    100.00 178.00   1.00    1.00    --  113.00 111.00  60.00   78
  9  \w     35.00 116.00   1.00    1.00    --  113.00-111.00-180.00   81
 10  \w     79.00 178.00   1.00    1.00    --  113.00  77.00 -60.00   99
 11  \w     38.00 141.00   1.00    1.00    --  113.00 -45.00-180.00  103
 12  \w     82.00 178.00   1.00    1.00    --  113.00  30.00 120.00   96
 13  \w     83.00 178.00   1.00    1.00    --  113.00  61.00-120.00   95
 14  \w    100.00 178.00   1.00    1.00    --  113.00 111.00 120.00   78
 15  \w     83.00 178.00   1.00    1.00    --  113.00  61.00  30.00   95
 16  \w     35.00 116.00   1.00    1.00    --  113.00-111.00   0.00   81
 17  \w     79.00 178.00   1.00    1.00    --  113.00  77.00 -90.00   99
 18  \w   -120.00  -8.00   1.00    1.00    --  -41.32 -77.00  60.00  112
 19  \w   -124.00 -79.00   1.00    1.00    --  -41.32 -99.00 -60.00   45
 20  \w   -120.00  -8.00   1.00    1.00    --  -41.32 -77.00-120.00  112
 21  \w   -115.00 -12.00   1.00    1.00    --  -41.32 -57.00 120.00  103
 22  \w   -115.00 -12.00   1.00    1.00    --  -41.32 -57.00 -30.00  103
 23  \w     29.00 109.00   1.00    1.00    --  113.00 -95.00  90.00   80
 24  \w     83.00 178.00   1.00    1.00    --  113.00  61.00 120.00   95
 25  \w     79.00 178.00   1.00    1.00    --  113.00  77.00-180.00   99
 26  \w     83.00 178.00   1.00    1.00    --  113.00  61.00-150.00   95
 27  \w     83.00 178.00   1.00    1.00    --  113.00  61.00  60.00   95
 28  \w     85.00 178.00   1.00    1.00    --  113.00  45.00   0.00   93
 29  \w     35.00 116.00   1.00    1.00    --  113.00-111.00  60.00   81
 30  \w     79.00 178.00   1.00    1.00    --  113.00  77.00-120.00   99
 31  \w     79.00 178.00   1.00    1.00    --  113.00  77.00   0.00   99
 32  \w     83.00 178.00   1.00    1.00    --  113.00  61.00 150.00   95
 33  \w   -115.00 -12.00   1.00    1.00    --  -41.32 -57.00-120.00  103
 34  \w   -124.00 -79.00   1.00    1.00    --  -41.32 -99.00 120.00   45
 35  \w   -120.00  -8.00   1.00    1.00    --  -41.32 -77.00-180.00  112
 36  \w   -120.00  -8.00   1.00    1.00    --  -41.32 -77.00 120.00  112
 37  \w      1.00  83.00   1.00    1.00    --   41.32 -99.00-180.00   82
 38  \w     79.00 178.00   1.00    1.00    --  113.00  77.00  90.00   99
 39  \w     83.00 178.00   1.00    1.00    --  113.00  61.00   0.00   95
 40  \w     79.00 178.00   1.00    1.00    --  113.00  77.00 150.00   99
 41  \w     83.00 178.00   1.00    1.00    --  113.00  61.00-180.00   95
 42  \w     79.00 178.00   1.00    1.00    --  113.00  77.00 120.00   99
 43  \w     85.00 178.00   1.00    1.00    --  113.00  45.00  60.00   93
 44  \w     79.00 178.00   1.00    1.00    --  113.00  77.00-150.00   99
 45  \w     83.00 178.00   1.00    1.00    --  113.00  61.00 -60.00   95
 46  \w    100.00 178.00   1.00    1.00    --  113.00 111.00-120.00   78
 47  \w     83.00 178.00   1.00    1.00    --  113.00  61.00 -30.00   95
 48  \w   -117.00 -15.00   1.00    1.00    --  -41.32 -38.00-180.00  102
 49  \w   -124.00 -79.00   1.00    1.00    --  -41.32 -99.00  30.00   45
 50  \w   -120.00  -8.00   1.00    1.00    --  -41.32 -77.00 -30.00  112
 51  \w   -124.00 -79.00   1.00    1.00    --  -41.32 -99.00-120.00   45
 52  \w   -117.00 -15.00   1.00    1.00    --  -41.32 -38.00 120.00  102
 53  \w     83.00 178.00   1.00    1.00    --  113.00  61.00 -90.00   95
 54  \w     85.00 178.00   1.00    1.00    --  113.00  45.00-120.00   93
 55  \w     83.00 178.00   1.00    1.00    --  113.00  61.00  90.00   95
 56  \w     35.00 116.00   1.00    1.00    --  113.00-111.00-150.00   81
 57  \w     79.00 178.00   1.00    1.00    --  113.00  77.00  30.00   99
 58  \w     79.00 178.00   1.00    1.00    --  113.00  77.00 -30.00   99
 59  \w     85.00 178.00   1.00    1.00    --  113.00  45.00 -30.00   93
 60  \w     29.00 109.00   1.00    1.00    --  113.00 -95.00  60.00   80
 61  \w     85.00 178.00   1.00    1.00    --  113.00  45.00-180.00   93
 62  \w     79.00 178.00   1.00    1.00    --  113.00  77.00  60.00   99
 63  \w   -117.00 -15.00   1.00    1.00    --  -41.32 -38.00-150.00  102
 64  \w   -115.00 -12.00   1.00    1.00    --  -41.32 -57.00 150.00  103
 65  \w   -120.00  -8.00   1.00    1.00    --  -41.32 -77.00 -60.00  112
 66  \w   -117.00 -15.00   1.00    1.00    --  -41.32 -38.00 -60.00  102
 67  \w     23.00  99.00   1.00    1.00    --   41.32-125.00 -60.00   76
 68  \w     85.00 178.00   1.00    1.00    --  113.00  45.00  90.00   93
 69  \w     82.00 178.00   1.00    1.00    --  113.00  30.00-180.00   96
 70  \w     85.00 178.00   1.00    1.00    --  113.00  45.00 -90.00   93
 71  \w     85.00 178.00   1.00    1.00    --  113.00  45.00 150.00   93
 72  \w     85.00 178.00   1.00    1.00    --  113.00  45.00 120.00   93
 73  \w     85.00 178.00   1.00    1.00    --  113.00  45.00 -60.00   93
 74  \w     82.00 178.00   1.00    1.00    --  113.00  30.00-150.00   96
 75  \w     85.00 178.00   1.00    1.00    --  113.00  45.00-150.00   93
;
_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      -0.0217679000
_diffrn_orient_matrix_UB_12      -0.0114433000
_diffrn_orient_matrix_UB_13      -0.0581157000
_diffrn_orient_matrix_UB_21      -0.0899186000
_diffrn_orient_matrix_UB_22      0.1478295000
_diffrn_orient_matrix_UB_23      -0.0025379000
_diffrn_orient_matrix_UB_31      0.2218806000
_diffrn_orient_matrix_UB_32      0.0587878000
_diffrn_orient_matrix_UB_33      -0.0049431000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            66747
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.721
_diffrn_reflns_theta_min         3.350
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.253
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70353
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_description       prism
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 3115 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.011(9)
_refine_ls_extinction_coef       0.0037(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     403
_refine_ls_number_reflns         6829
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0334
_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^)+(0.0620P)^2^+0.3797P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0902
_refine_ls_wR_factor_ref         0.0908
_reflns_Friedel_coverage         0.880
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                6751
_reflns_number_total             6829
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob01888c2.cif
_cod_data_source_block           uk
_cod_depositor_comments
'Adding full bibliography for 7157119--7157120.cif.'
_cod_database_code               7157120
_shelx_shelxl_version_number     2016/6
_shelx_res_checksum              51753