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_7157119
_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         'C43 H54 N2 O7'
_chemical_formula_sum            'C43 H54 N2 O7'
_chemical_formula_weight         710.88
_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             2018-06-19
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2018-08-06 deposited with the CCDC.    2019-09-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.1135(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.28330(3)
_cell_length_b                   33.99155(12)
_cell_length_c                   8.90762(5)
_cell_measurement_reflns_used    91552
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.4760
_cell_measurement_theta_min      3.8850
_cell_volume                     1818.247(16)
_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      100.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4052
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_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    -85.00  17.00   1.00    1.00    --  -41.32 103.00   8.00  102
  2  \w      5.00  85.00   1.00    1.00    --   41.32-103.00 -93.00   80
  3  \w    101.00 178.00   1.00    1.63    --  113.00 103.00   8.00   77
  4  \w     32.00 112.00   1.00    1.63    --  113.00-103.00 -93.00   80
  5  \w   -115.00 -12.00   1.00    1.00    --  -41.32 -57.00  90.00  103
  6  \w   -124.00 -79.00   1.00    1.00    --  -41.32 -99.00  30.00   45
  7  \w   -117.00 -15.00   1.00    1.00    --  -41.32 -38.00-180.00  102
  8  \w      1.00  83.00   1.00    1.00    --   41.32 -99.00 150.00   82
  9  \w     85.00 178.00   1.00    1.63    --  113.00  45.00  60.00   93
 10  \w     29.00 109.00   1.00    1.63    --  113.00 -95.00 150.00   80
 11  \w     29.00 109.00   1.00    1.63    --  113.00 -95.00  30.00   80
 12  \w     35.00 116.00   1.00    1.63    --  113.00-111.00-120.00   81
 13  \w     82.00 178.00   1.00    1.63    --  113.00  30.00 150.00   96
 14  \w     36.00 118.00   1.00    1.63    --  113.00-116.00 127.83   82
 15  \w     82.00 178.00   1.00    1.63    --  113.00  30.00 -90.00   96
 16  \w     57.00 150.00   1.00    1.63    --  113.00 178.00 150.00   93
 17  \w     35.00 116.00   1.00    1.63    --  113.00-111.00 -30.00   81
 18  \w     35.00 116.00   1.00    1.63    --  113.00-111.00   0.00   81
 19  \w     83.00 178.00   1.00    1.63    --  113.00  61.00  90.00   95
 20  \w   -120.00  -8.00   1.00    1.00    --  -41.32 -77.00 -60.00  112
 21  \w   -120.00  -8.00   1.00    1.00    --  -41.32 -77.00-150.00  112
 22  \w   -115.00 -12.00   1.00    1.00    --  -41.32 -57.00 -60.00  103
 23  \w   -124.00 -79.00   1.00    1.00    --  -41.32 -99.00-180.00   45
 24  \w   -120.00  -8.00   1.00    1.00    --  -41.32 -77.00  60.00  112
 25  \w     83.00 178.00   1.00    1.63    --  113.00  61.00-180.00   95
 26  \w     85.00 178.00   1.00    1.63    --  113.00  45.00  42.64   93
 27  \w     85.00 178.00   1.00    1.63    --  113.00  45.00 -30.00   93
 28  \w     83.00 178.00   1.00    1.63    --  113.00  61.00 150.00   95
 29  \w     83.00 178.00   1.00    1.63    --  113.00  58.00-149.51   95
 30  \w     79.00 178.00   1.00    1.63    --  113.00  77.00 -90.00   99
 31  \w    100.00 178.00   1.00    1.63    --  113.00 111.00 -60.00   78
 32  \w     79.00 178.00   1.00    1.63    --  113.00  77.00-120.00   99
 33  \w     85.00 178.00   1.00    1.63    --  113.00  45.00   0.00   93
 34  \w     83.00 178.00   1.00    1.63    --  113.00  61.00   0.00   95
 35  \w   -115.00 -12.00   1.00    1.00    --  -41.32 -57.00 150.00  103
 36  \w   -124.00 -79.00   1.00    1.00    --  -41.32 -99.00 150.00   45
 37  \w   -120.00  -8.00   1.00    1.00    --  -41.32 -77.00 120.00  112
 38  \w   -117.00 -15.00   1.00    1.00    --  -41.32 -38.00  30.00  102
 39  \w   -117.00 -15.00   1.00    1.00    --  -41.32 -38.00 -60.00  102
 40  \w     79.00 178.00   1.00    1.63    --  113.00  77.00 120.00   99
 41  \w     79.00 178.00   1.00    1.63    --  113.00  77.00  30.00   99
 42  \w     83.00 178.00   1.00    1.63    --  113.00  61.00  60.00   95
 43  \w     84.00 178.00   1.00    1.63    --  113.00  56.00  83.33   94
 44  \w     83.00 178.00   1.00    1.63    --  113.00  61.00 -60.00   95
 45  \w     79.00 178.00   1.00    1.63    --  113.00  77.00-150.00   99
 46  \w     79.00 178.00   1.00    1.63    --  113.00  77.00  90.00   99
 47  \w     83.00 178.00   1.00    1.63    --  113.00  61.00 -30.00   95
 48  \w     83.00 178.00   1.00    1.63    --  113.00  61.00 -90.00   95
 49  \w     83.00 178.00   1.00    1.63    --  113.00  60.00 164.61   95
 50  \w   -117.00 -15.00   1.00    1.00    --  -41.32 -38.00-120.00  102
 51  \w   -120.00  -8.00   1.00    1.00    --  -41.32 -77.00 -90.00  112
 52  \w   -115.00 -12.00   1.00    1.00    --  -41.32 -57.00  60.00  103
 53  \w   -120.00  -8.00   1.00    1.00    --  -41.32 -77.00  30.00  112
 54  \w     23.00  99.00   1.00    1.00    --   41.32-125.00 -30.00   76
 55  \w     83.00 178.00   1.00    1.63    --  113.00  61.00 120.00   95
 56  \w     79.00 178.00   1.00    1.63    --  113.00  77.00-180.00   99
 57  \w     83.00 178.00   1.00    1.63    --  113.00  61.00-120.00   95
 58  \w     80.00 178.00   1.00    1.63    --  113.00  75.00  -9.98   98
 59  \w     35.00 116.00   1.00    1.63    --  113.00-111.00 -60.00   81
 60  \w     79.00 178.00   1.00    1.63    --  113.00  77.00   0.00   99
 61  \w     79.00 178.00   1.00    1.63    --  113.00  77.00 -60.00   99
 62  \w     83.00 178.00   1.00    1.63    --  113.00  60.00  69.85   95
 63  \w     82.00 178.00   1.00    1.63    --  113.00  63.00  30.43   96
 64  \w     79.00 178.00   1.00    1.63    --  113.00  77.00 -30.00   99
 65  \w    -48.00 131.00   1.00    1.00    --   41.32   0.00 -60.00  179
 66  \w    -48.00 131.00   1.00    1.00    --   41.32   0.00 -90.00  179
 67  \w    -48.00 131.00   1.00    1.00    --   41.32   0.00-180.00  179
 68  \w    -48.00 131.00   1.00    1.00    --   41.32   0.00-120.00  179
 69  \w    -48.00 131.00   1.00    1.00    --   41.32   0.00-150.00  179
 70  \w     84.00 178.00   1.00    1.63    --  113.00  51.00 144.05   94
 71  \w     85.00 178.00   1.00    1.63    --  113.00  45.00 -60.00   93
 72  \w     39.00 143.00   1.00    1.63    --  113.00 -61.00  30.00  104
 73  \w     79.00 178.00   1.00    1.63    --  113.00  77.00 150.00   99
 74  \w     82.00 178.00   1.00    1.63    --  113.00  62.00  39.33   96
 75  \w     85.00 178.00   1.00    1.63    --  113.00  45.00 120.00   93
 76  \w     83.00 178.00   1.00    1.63    --  113.00  61.00-150.00   95
 77  \w     83.00 178.00   1.00    1.63    --  113.00  59.00 -95.23   95
 78  \w     79.00 178.00   1.00    1.63    --  113.00  77.00  60.00   99
 79  \w     85.00 178.00   1.00    1.63    --  113.00  45.00 -90.00   93
 80  \w    -48.00 131.00   1.00    1.00    --   41.32   0.00  90.00  179
 81  \w    -48.00 131.00   1.00    1.00    --   41.32   0.00  60.00  179
 82  \w    -48.00 131.00   1.00    1.00    --   41.32   0.00 -30.00  179
 83  \w    -48.00 131.00   1.00    1.00    --   41.32   0.00  30.00  179
 84  \w    -48.00 131.00   1.00    1.00    --   41.32   0.00   0.00  179
 85  \w     52.00 178.00   1.00    1.63    --  113.00  15.00 -90.00  126
 86  \w     81.00 178.00   1.00    1.63    --  113.00  70.00-111.83   97
 87  \w     39.00 143.00   1.00    1.63    --  113.00 -61.00-120.00  104
 88  \w     82.00 178.00   1.00    1.63    --  113.00  30.00 -30.00   96
 89  \w     83.00 178.00   1.00    1.63    --  113.00  57.00  35.08   95
 90  \w     85.00 178.00   1.00    1.63    --  113.00  45.00  90.00   93
 91  \w     38.00 141.00   1.00    1.63    --  113.00 -45.00 120.00  103
 92  \w     35.00 116.00   1.00    1.63    --  113.00-111.00 -90.00   81
 93  \w     86.00 178.00   1.00    1.63    --  113.00  41.00  27.75   92
 94  \w     85.00 178.00   1.00    1.63    --  113.00  45.00-120.00   93
 95  \w   -131.00  48.00   1.00    1.00    --  -41.32   0.00-180.00  179
 96  \w   -131.00  48.00   1.00    1.00    --  -41.32   0.00-150.00  179
 97  \w   -131.00  48.00   1.00    1.00    --  -41.32   0.00-120.00  179
 98  \w    -48.00 131.00   1.00    1.00    --   41.32   0.00 150.00  179
 99  \w    -48.00 131.00   1.00    1.00    --   41.32   0.00 120.00  179
100  \w     85.00 178.00   1.00    1.63    --  113.00  45.00  30.00   93
101  \w     24.00 178.00   1.00    1.63    --  113.00   0.00-120.00  154
102  \w     86.00 178.00   1.00    1.63    --  113.00  42.00 -60.48   92
103  \w     24.00 178.00   1.00    1.63    --  113.00   0.00-150.00  154
104  \w     24.00 178.00   1.00    1.63    --  113.00   0.00-180.00  154
105  \w     83.00 178.00   1.00    1.63    --  113.00  57.00 141.99   95
106  \w     24.00 178.00   1.00    1.63    --  113.00   0.00 -90.00  154
107  \w     24.00 178.00   1.00    1.63    --  113.00   0.00 -60.00  154
108  \w     24.00 178.00   1.00    1.63    --  113.00   0.00 -30.00  154
109  \w     85.00 178.00   1.00    1.63    --  113.00  45.00 150.00   93
110  \w   -131.00  48.00   1.00    1.00    --  -41.32   0.00  30.00  179
111  \w   -131.00  48.00   1.00    1.00    --  -41.32   0.00   0.00  179
112  \w   -131.00  48.00   1.00    1.00    --  -41.32   0.00 -90.00  179
113  \w   -131.00  48.00   1.00    1.00    --  -41.32   0.00 -30.00  179
114  \w   -131.00  48.00   1.00    1.00    --  -41.32   0.00 -60.00  179
115  \w     24.00 178.00   1.00    1.63    --  113.00   0.00  30.00  154
116  \w     24.00 178.00   1.00    1.63    --  113.00   0.00-180.00  154
117  \w     24.00 178.00   1.00    1.63    --  113.00   0.00   0.00  154
118  \w     24.00 178.00   1.00    1.63    --  113.00   0.00 150.00  154
119  \w     24.00 178.00   1.00    1.63    --  113.00   0.00 120.00  154
120  \w     24.00 178.00   1.00    1.63    --  113.00   0.00  90.00  154
121  \w     24.00 178.00   1.00    1.63    --  113.00   0.00-150.00  154
122  \w     24.00 178.00   1.00    1.63    --  113.00   0.00-120.00  154
123  \w     24.00 140.00   1.00    1.63    --  113.00   0.00 -90.00  116
124  \w     24.00 178.00   1.00    1.63    --  113.00   0.00  60.00  154
;
_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      -0.1495647000
_diffrn_orient_matrix_UB_12      -0.0320930000
_diffrn_orient_matrix_UB_13      -0.0999564000
_diffrn_orient_matrix_UB_21      -0.1944349000
_diffrn_orient_matrix_UB_22      0.0294867000
_diffrn_orient_matrix_UB_23      -0.0485582000
_diffrn_orient_matrix_UB_31      0.0750766000
_diffrn_orient_matrix_UB_32      0.0124336000
_diffrn_orient_matrix_UB_33      -0.1428380000
_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  0.0371
_diffrn_reflns_av_sigmaI/netI    0.0345
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            152149
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.554
_diffrn_reflns_theta_min         2.600
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.701
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_correction_T_min  0.804
_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    1.298
_exptl_crystal_description       prism
_exptl_crystal_F_000             764
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 3642 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(3)
_refine_ls_extinction_coef       0.0019(2)
_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   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     477
_refine_ls_number_reflns         7605
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0268
_refine_ls_R_factor_gt           0.0262
_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^)+(0.0394P)^2^+0.4189P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0674
_refine_ls_wR_factor_ref         0.0679
_reflns_Friedel_coverage         0.961
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                7530
_reflns_number_total             7605
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob01888c2.cif
_cod_data_source_block           26a
_cod_depositor_comments
'Adding full bibliography for 7157119--7157120.cif.'
_cod_original_cell_volume        1818.246(16)
_cod_database_code               7157119
_shelx_shelxl_version_number     2016/6
_shelx_res_checksum              87430