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_1572167
_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 S
_chemical_formula_moiety         'C42 H49 O4, C46 H52.5 O4'
_chemical_formula_sum            'C88.5 H95 O8'
_chemical_formula_weight         1286.64
_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.cc2gn7x9
_audit_creation_date             2023-07-12
_audit_creation_method
;FinalCif V123 by Daniel Kratzert, Freiburg 2023, 
https://dkratzert.de/finalcif.html
;
_audit_update_record
;
2023-07-21 deposited with the CCDC.	2024-07-25 downloaded from the CCDC.
;
_cell_angle_alpha                105.9310(10)
_cell_angle_beta                 93.8630(10)
_cell_angle_gamma                90.3130(10)
_cell_formula_units_Z            1
_cell_length_a                   7.45270(10)
_cell_length_b                   16.7911(2)
_cell_length_c                   18.3652(3)
_cell_measurement_reflns_used    21695
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      67.9960
_cell_measurement_theta_min      2.4870
_cell_volume                     2204.23(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.992
_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    -68.00  28.00   0.50    1.00    --  -41.33  78.00  69.00  192
  2  \w   -110.00 -13.00   0.50    8.00    --  -82.50  78.00  69.00  194
  3  \w   -152.00 -78.00   0.50    8.00    --  -82.50 -78.00 -55.00  148
  4  \w    100.00 165.00   0.50    8.00    --   96.67  78.00  69.00  130
  5  \w    -28.00  30.00   0.50    1.00    --  -41.33  21.00 -30.00  116
  6  \w   -109.00 -28.00   0.50    1.00    --  -41.33 -32.00 -30.00  162
  7  \w    -37.00  27.00   0.50    1.00    --  -41.33  32.00-150.00  128
  8  \w   -108.00 -21.00   0.50    1.00    --  -41.33 -54.00-120.00  174
  9  \w    -24.00  35.00   0.50    1.00    --  -41.33  11.00  90.00  118
 10  \w     18.00  80.00   0.50    1.00    --   41.33-104.00-180.00  124
 11  \w    -22.00  69.00   0.50    1.00    --   41.33 -78.00 -55.00  182
 12  \w     41.00 100.00   0.50    1.00    --   41.33-138.00   0.00  118
 13  \w     10.00  42.00   0.50    1.00    --   41.33  91.00-139.47   64
 14  \w    -34.00  24.00   0.50    1.00    --   41.33 -11.00  60.00  116
 15  \w    -30.00  28.00   0.50    1.00    --   41.33 -21.00-120.00  116
 16  \w     10.00  42.00   0.50    1.00    --   41.33  91.00 -79.97   64
 17  \w     15.00 110.00   0.50    1.00    --   41.33  77.00 120.00  190
 18  \w    -34.00  24.00   0.50    1.00    --   41.33 -11.00   0.00  116
 19  \w     41.00 100.00   0.50    1.00    --   41.33-138.00 150.00  118
 20  \w   -150.00 -58.00   0.50    8.00    --  -82.50 -68.00   0.00  184
 21  \w   -157.00 -83.00   0.50    8.00    --  -82.50 -96.00  60.00  148
 22  \w    -47.00 -15.00   0.50    8.00    --  -82.50  42.00  60.00   64
 23  \w    -47.00 -15.00   0.50    8.00    --  -82.50  42.00  90.00   64
 24  \w    -47.00 -15.00   0.50    8.00    --  -82.50  42.00-150.00   64
 25  \w    -47.00 -15.00   0.50    8.00    --  -82.50  42.00 -60.00   64
 26  \w     70.00 165.00   0.50    8.00    --   96.67  77.00  90.00  190
 27  \w     44.00 127.00   0.50    8.00    --   96.67-145.00 -30.00  166
 28  \w     30.00 109.00   0.50    8.00    --   96.67-117.00-150.00  158
 29  \w     81.00 164.00   0.50    8.00    --   96.67 145.00   0.00  166
 30  \w     29.00  83.00   0.50    8.00    --   96.67 -68.00-180.00  108
 31  \w     30.00 109.00   0.50    8.00    --   96.67-117.00 120.00  158
 32  \w     30.00  57.00   0.50    8.00    --   96.67 -50.00  30.00   54
 33  \w     30.00  57.00   0.50    8.00    --   96.67 -50.00 -60.00   54
 34  \w     78.00 163.00   0.50    8.00    --   96.67  50.00-150.00  170
 35  \w     30.00 109.00   0.50    8.00    --   96.67-117.00-120.00  158
 36  \w     30.00  57.00   0.50    8.00    --   96.67 -50.00-180.00   54
 37  \w     44.00 127.00   0.50    8.00    --   96.67-145.00-150.00  166
 38  \w     37.00 174.00   0.50    8.00    --   96.67   8.00  60.00  274
 39  \w     82.00 167.00   0.50    8.00    --   96.67  25.00-150.00  170
 40  \w     44.00 127.00   0.50    8.00    --   96.67-145.00  60.00  166
 41  \w     30.00 109.00   0.50    8.00    --   96.67-117.00  60.00  158
 42  \w     83.00 164.00   0.50    8.00    --   96.67  33.00  60.00  162
 43  \w     29.00  68.00   0.50    8.00    --   96.67 -59.00-120.00   78
 44  \w     73.00 165.00   0.50    8.00    --   96.67  68.00 120.00  184
 45  \w     28.00 105.00   0.50    8.00    --   96.67 -77.00  30.00  154
 46  \w    105.00 170.00   0.50    8.00    --   96.67  96.00   0.00  130
 47  \w     30.00 109.00   0.50    8.00    --   96.67-117.00 -30.00  158
 48  \w     29.00  83.00   0.50    8.00    --   96.67 -68.00  30.00  108
 49  \w     81.00 164.00   0.50    8.00    --   96.67 145.00-120.00  166
 50  \w     27.00 110.00   0.50    8.00    --   96.67 -78.00 -55.00  166
 51  \w   -109.00 -18.00   0.50    1.00    --  -41.33 -65.00 150.00  182
 52  \w   -109.00 -18.00   0.50    1.00    --  -41.33 -65.00-180.00  182
 53  \w   -108.00 -21.00   0.50    1.00    --  -41.33 -54.00-180.00  174
 54  \w   -110.00 -14.00   0.50    1.00    --  -41.33 -77.00 -30.00  192
 55  \w   -109.00 -28.00   0.50    1.00    --  -41.33 -32.00  30.00  162
 56  \w   -110.00 -18.00   0.50    1.00    --  -41.33 -63.00  37.61  184
 57  \w      9.00  42.00   0.50    1.00    --   41.33  92.00 142.78   66
 58  \w     13.00  43.00   0.50    1.00    --   41.33  83.00 -48.97   60
 59  \w     12.00  43.00   0.50    1.00    --   41.33  84.00-173.73   62
 60  \w     25.00 109.00   0.50    1.00    --   41.33  43.00 -60.00  168
 61  \w     10.00  42.00   0.50    1.00    --   41.33  91.00  46.79   64
 62  \w     13.00  43.00   0.50    1.00    --   41.33  81.00-130.66   60
 63  \w      9.00  42.00   0.50    1.00    --   41.33  92.00 -83.33   66
 64  \w     10.00  42.00   0.50    1.00    --   41.33  91.00  72.34   64
 65  \w     12.00  43.00   0.50    1.00    --   41.33  84.00 -10.10   62
 66  \w   -151.00 -55.00   0.50    8.00    --  -82.50 -77.00 -30.00  192
 67  \w     73.00 161.00   0.50    8.00    --   96.67  68.00 -90.00  176
 68  \w     73.00 165.00   0.50    8.00    --   96.67  68.00  60.00  184
 69  \w     73.00 165.00   0.50    8.00    --   96.67  68.00 150.00  184
 70  \w     73.00 165.00   0.50    8.00    --   96.67  68.00-120.00  184
;
_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      0.0550300000
_diffrn_orient_matrix_UB_12      0.0173662000
_diffrn_orient_matrix_UB_13      -0.0736619000
_diffrn_orient_matrix_UB_21      -0.1815190000
_diffrn_orient_matrix_UB_22      0.0413132000
_diffrn_orient_matrix_UB_23      -0.0081141000
_diffrn_orient_matrix_UB_31      0.0835116000
_diffrn_orient_matrix_UB_32      0.0842671000
_diffrn_orient_matrix_UB_33      0.0464465000
_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  0.0412
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            38540
_diffrn_reflns_point_group_measured_fraction_full 0.850
_diffrn_reflns_point_group_measured_fraction_max 0.843
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.186
_diffrn_reflns_theta_min         2.508
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.474
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74562
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.115a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    0.969
_exptl_crystal_description       block
_exptl_crystal_F_000             690
_exptl_crystal_size_max          0.371
_exptl_crystal_size_mid          0.205
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.731
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.2(3)
_refine_ls_extinction_coef       0.0039(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1031
_refine_ls_number_reflns         13589
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.128
_refine_ls_R_factor_all          0.0849
_refine_ls_R_factor_gt           0.0813
_refine_ls_shift/su_max          3.614
_refine_ls_shift/su_mean         0.085
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1811P)^2^+0.0703P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2294
_refine_ls_wR_factor_ref         0.2368
_reflns_Friedel_coverage         0.700
_reflns_Friedel_fraction_full    0.703
_reflns_Friedel_fraction_max     0.695
_reflns_number_gt                12300
_reflns_number_total             13589
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc04103h3.cif
_cod_data_source_block           sk02101ayan_cm01
_cod_original_formula_sum        'C88.50 H95 O8'
_cod_database_code               1572167
_chemical_oxdiff_formula         'C H O'
_chemical_oxdiff_usercomment     '100 K'
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 1.2(3)
 -0.2(3)
2. 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
3. Others
 Fixed Sof: O4A(0.5) H3(0) H74(0.5) H32a(0.5) H32b(0.5) O4(0.5) C33A(0.5)
 C34A(0.5) C39A(0.5) H39a(0.5) H39b(0.5) H39c(0.5) C76(0.5) H76(0.5) O8(0.5)
 C80(0.5) H80a(0.5) H80b(0.5) H80c(0.5) C77(0.5) C79(0.5) H79(0.5) C39(0.5)
 H39d(0.5) H39e(0.5) H39f(0.5) C40(0.5) H40(0.5) C81(0.5) C82A(0.5) C40A(0.5)
 H40A(0.5) C41A(0.5) H41a(0.5) H41b(0.5) H41c(0.5) O8A(0.5) C80A(0.5) H80d(0.5)
 H80e(0.5) H80f(0.5) C77A(0.5) C81A(0.5) H81A(0.5) C78A(0.5) C41(0.5) H41d(0.5)
 H41e(0.5) H41f(0.5) C78(0.5) C42A(0.5) H42a(0.5) H42b(0.5) H42c(0.5) C76A(0.5)
 H76A(0.5) C82(0.5) H82a(0.5) H82b(0.5) H82c(0.5) C42(0.5) H42d(0.5) H42e(0.5)
 H42f(0.5) C34(0.5) C33(0.5) C79A(0.5) H79A(0.5) C83A(0.5) C83(0.5) H83a(0.5)
 H83b(0.5) H83c(0.5)
4.a Ternary CH refined with riding coordinates:
 C29(H29), C54(H54), C13(H13), C70(H70), C45(H45), C74(H74), C40(H40),
 C40A(H40A), C81A(H81A)
4.b Secondary CH2 refined with riding coordinates:
 C22(H22a,H22b), C62(H62a,H62b), C66(H66a,H66b), C60(H60a,H60b), C11(H11a,
 H11b), C63(H63a,H63b), C19(H19a,H19b), C53(H53a,H53b), C21(H21a,H21b),
 C68(H68a,H68b), C12(H12a,H12b), C25(H25a,H25b), C27(H27a,H27b), C31(H31a,H31b),
  C52(H52a,H52b), C32(H32a,H32b), C72(H72a,H72b), C73(H73a,H73b)
4.c Aromatic/amide H refined with riding coordinates:
 C47(H47), C6(H6), C9(H9), C3(H3), C50(H50), C38A(H38A), C76(H76), C35A(H35A),
 C79(H79), C35(H35), C38(H38), C76A(H76A), C79A(H79A)
4.d X=CH2 refined with riding coordinates:
 C61(H61a,H61b), C20(H20a,H20b)
4.e Idealised Me refined as rotating group:
 C56(H56a,H56b,H56c), C15(H15a,H15b,H15c), C51(H51a,H51b,H51c), C10(H10a,H10b,
 H10c), C30(H30a,H30b,H30c), C71(H71a,H71b,H71c), C43(H43a,H43b,H43c), C44(H44a,
 H44b,H44c), C39A(H39a,H39b,H39c), C1(H1a,H1b,H1c), C80(H80a,H80b,H80c), C2(H2a,
 H2b,H2c), C39(H39d,H39e,H39f), C41A(H41a,H41b,H41c), C80A(H80d,H80e,H80f),
 C41(H41d,H41e,H41f), C42A(H42a,H42b,H42c), C82(H82a,H82b,H82c), C42(H42d,H42e,
 H42f), C83(H83a,H83b,H83c)
;
_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 1.287
_oxdiff_exptl_absorpt_empirical_full_min 0.790
_shelx_shelxl_version_number     2018/3
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_estimated_absorpt_t_min   0.844
_shelx_estimated_absorpt_t_max   0.941
_shelx_res_checksum              39596
_shelx_hkl_checksum              80255
_shelx_fab_checksum              51919