Biomimetic total synthesis of the reported structure of (+)-selaginedorffone B
Kundu, Sourav; Jana, Debgopal; Mandal, Nilangshu; Mondal, Ayan; Murmu, Ranjit; Roy, Nanda Kishore; Datta, Ayan; Bisai, Alakesh; Chemical Science  (2024) –; doi:10.1039/D4SC04103H

data_1572169
_publ_section_title
;
 Biomimetic total synthesis of the reported structure of
 (+)-selaginedorffone B
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D4SC04103H
_journal_year                    2024
_chemical_absolute_configuration syn
_chemical_formula_moiety         '0.5(C42 H43 O6), 0.5(C42 H46 O6)'
_chemical_formula_sum            'C42 H46 O6'
_chemical_formula_weight         646.79
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2ftx06
_audit_creation_date             2023-04-26
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-04-26 deposited with the CCDC.	2024-07-25 downloaded from the CCDC.
;
_cell_angle_alpha                86.519(2)
_cell_angle_beta                 86.864(2)
_cell_angle_gamma                67.266(3)
_cell_formula_units_Z            2
_cell_length_a                   6.2642(3)
_cell_length_b                   8.0505(2)
_cell_length_c                   36.8967(6)
_cell_measurement_reflns_used    12182
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      68.1220
_cell_measurement_theta_min      2.3740
_cell_volume                     1711.99(10)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full value
_diffrn_measured_fraction_theta_max 0.884
_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    -33.00  29.00   0.50    0.80    --  -40.33  28.00-115.00  124
  2  \w   -109.00 -27.00   0.50    0.80    --  -40.33 -28.00  82.00  164
  3  \w   -152.00 -69.00   0.50    3.33    --  -82.50 -28.00  82.00  166
  4  \w     84.00 166.00   0.50    3.33    --   96.67  28.00-115.00  164
  5  \w    -63.00  27.00   0.50    0.80    --  -40.33  64.00 -60.00  180
  6  \w    -78.00   4.00   0.50    0.80    --  -40.33 104.00-180.00  164
  7  \w    -24.00  35.00   0.50    0.80    --  -40.33  12.00  30.00  118
  8  \w    -24.00  35.00   0.50    0.80    --  -40.33  12.00 120.00  118
  9  \w     27.00 110.00   0.50    0.80    --   40.33  28.00-115.00  166
 10  \w    -35.00  24.00   0.50    0.80    --   40.33 -12.00 -90.00  118
 11  \w    -35.00  24.00   0.50    0.80    --   40.33 -12.00-150.00  118
 12  \w    -29.00  33.00   0.50    0.80    --   40.33 -28.00  82.00  124
 13  \w     41.00  99.00   0.50    0.80    --   40.33-138.00 -90.00  116
 14  \w    -47.00 -15.00   0.50    3.33    --  -82.50  42.00-150.00   64
 15  \w    -47.00 -15.00   0.50    3.33    --  -82.50  42.00-120.00   64
 16  \w    -56.00 -16.00   0.50    3.33    --  -82.50  50.00 -30.00   80
 17  \w    -47.00 -15.00   0.50    3.33    --  -82.50  42.00-180.00   64
 18  \w   -149.00 -78.00   0.50    3.33    --  -82.50-117.00-150.00  142
 19  \w     30.00  57.00   0.50    3.33    --   96.67 -50.00-180.00   54
 20  \w     30.00  57.00   0.50    3.33    --   96.67 -50.00-150.00   54
 21  \w     30.00 109.00   0.50    3.33    --   96.67-117.00 -60.00  158
 22  \w     44.00 127.00   0.50    3.33    --   96.67-145.00  30.00  166
 23  \w     29.00  83.00   0.50    3.33    --   96.67 -68.00  30.00  108
 24  \w     29.00  68.00   0.50    3.33    --   96.67 -59.00  60.00   78
 25  \w     82.00 167.00   0.50    3.33    --   96.67  25.00   0.00  170
 26  \w     44.00 127.00   0.50    3.33    --   96.67-145.00-180.00  166
 27  \w     29.00  68.00   0.50    3.33    --   96.67 -59.00 -30.00   78
 28  \w     30.00  57.00   0.50    3.33    --   96.67 -50.00 -30.00   54
 29  \w     29.00  68.00   0.50    3.33    --   96.67 -59.00-180.00   78
 30  \w     29.00  83.00   0.50    3.33    --   96.67 -68.00-180.00  108
 31  \w     83.00 164.00   0.50    3.33    --   96.67  33.00 -90.00  162
 32  \w     99.00 164.00   0.50    3.33    --   96.67 117.00 -60.00  130
 33  \w    105.00 170.00   0.50    3.33    --   96.67  96.00  60.00  130
 34  \w     30.00  57.00   0.50    3.33    --   96.67 -50.00 120.00   54
 35  \w     29.00  83.00   0.50    3.33    --   96.67 -68.00 120.00  108
 36  \w     29.00  83.00   0.50    3.33    --   96.67 -68.00 -60.00  108
 37  \w   -109.00 -13.00   0.50    0.80    --  -40.33 -77.00 -90.00  192
 38  \w   -109.00 -13.00   0.50    0.80    --  -40.33 -77.00   0.00  192
 39  \w   -109.00 -13.00   0.50    0.80    --  -40.33 -77.00 -30.00  192
 40  \w   -108.00 -17.00   0.50    0.80    --  -40.33 -64.00  30.00  182
 41  \w   -109.00 -13.00   0.50    0.80    --  -40.33 -77.00  90.00  192
 42  \w   -108.00 -17.00   0.50    0.80    --  -40.33 -64.00 150.00  182
 43  \w    -27.00  64.00   0.50    0.80    --   40.33 -64.00  30.00  182
 44  \w     14.00 109.00   0.50    0.80    --   40.33  77.00-180.00  190
 45  \w     14.00 109.00   0.50    0.80    --   40.33  77.00-120.00  190
 46  \w     14.00 109.00   0.50    0.80    --   40.33  77.00 -60.00  190
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0077092000
_diffrn_orient_matrix_UB_12      0.1808219000
_diffrn_orient_matrix_UB_13      0.0128529000
_diffrn_orient_matrix_UB_21      -0.0129411000
_diffrn_orient_matrix_UB_22      -0.0660111000
_diffrn_orient_matrix_UB_23      0.0398227000
_diffrn_orient_matrix_UB_31      0.2663736000
_diffrn_orient_matrix_UB_32      -0.0779328000
_diffrn_orient_matrix_UB_33      0.0008836000
_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  0.0472
_diffrn_reflns_av_unetI/netI     0.0466
_diffrn_reflns_Laue_measured_fraction_full 0.891
_diffrn_reflns_Laue_measured_fraction_max 0.884
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            17137
_diffrn_reflns_point_group_measured_fraction_full 0.652
_diffrn_reflns_point_group_measured_fraction_max 0.646
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.400
_diffrn_reflns_theta_min         2.401
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.658
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45746
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic whiteish white'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_description       needle
_exptl_crystal_F_000             692
_exptl_crystal_size_max          0.947
_exptl_crystal_size_mid          0.129
_exptl_crystal_size_min          0.059
_refine_diff_density_max         1.163
_refine_diff_density_min         -0.721
_refine_diff_density_rms         0.157
_refine_ls_abs_structure_details
;
 Flack x determined using 2374 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.828
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     880
_refine_ls_number_reflns         8151
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.828
_refine_ls_R_factor_all          0.1242
_refine_ls_R_factor_gt           0.1227
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3578
_refine_ls_wR_factor_ref         0.3615
_reflns_Friedel_coverage         0.461
_reflns_Friedel_fraction_full    0.413
_reflns_Friedel_fraction_max     0.407
_reflns_number_gt                7862
_reflns_number_total             8151
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc04103h3.cif
_cod_data_source_block           sk-0284_auto_kp260423
_cod_database_code               1572169
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C H O'
_chemical_oxdiff_usercomment     '100 K'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00L(H00L), C00V(H00V), C012(H012), C019(H019), C01F(H01Y), C01W(H4),
 C023(H023), C02L(H02L)
2.b Secondary CH2 refined with riding coordinates:
 C00C(H00B,H00C), C00J(H00D,H00E), C00K(H00I,H00J), C00X(H00K,H00M), C015(H01A,
 H01B), C018(H01R,H01S), C01C(H01F,H01G), C01E(H01W,H01X), C01I(H01H,H01I),
 C01M(H1,HD), C01O(H01J,H01K), C01R(H2,HE), C02A(H02T,H02U), C02C(H02D,H02E)
2.c Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00O(H00O), C00R(H00R), C011(H011), C020(H020), C025(H025),
 C02F(H02F), C02K(H02V)
2.d Idealised Me refined as rotating group:
 C00P(H00F,H00G,H00H), C01A(H01C,H01D,H01E), C01D(H01T,H01U,H01V), C01K(H01Z,H,
 HA), C01L(H01,HB,HC), C01S(H3,HF,HG), C01T(H01L,H01M,H01N), C01X(H5,HH,HI),
 C01Z(H01O,H01P,H01Q), C022(H02A,H02B,H02C), C024(H02N,H02O,H02P), C028(H02Q,
 H02R,H02S), C02I(H02G,H02H,H02I), C02M(H02J,H02K,H02M), C4(H4A,H4B,H4C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              20999
_shelx_hkl_checksum              98192
_shelx_fab_checksum              25581
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.479
_oxdiff_exptl_absorpt_empirical_full_min 0.435