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_1572168
_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         'C21 H26 O3'
_chemical_formula_sum            'C21 H26 O3'
_chemical_formula_weight         326.41
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2ftty1
_audit_creation_date             2023-04-26
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-04-26 deposited with the CCDC.	2024-07-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   6.79620(10)
_cell_length_b                   21.0544(2)
_cell_length_c                   25.6129(2)
_cell_measurement_reflns_used    29920
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      68.1950
_cell_measurement_theta_min      2.1110
_cell_volume                     3664.95(7)
_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  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_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    -61.00  28.00   0.50    0.20    --  -40.33  57.00  71.00  178
  2  \w    -31.00  30.00   0.50    0.20    --  -40.33  25.00   0.00  122
  3  \w    -24.00  35.00   0.50    0.20    --  -40.33  12.00 -90.00  118
  4  \w    -24.00  35.00   0.50    0.20    --  -40.33  12.00-180.00  118
  5  \w    -63.00  28.00   0.50    0.20    --  -40.33  63.00-103.00  182
  6  \w     34.00  92.00   0.50    0.20    --   40.33-126.00  56.00  116
  7  \w     28.00  74.00   0.50    0.28    --   96.67 -63.00 119.00   92
  8  \w     29.00  83.00   0.50    0.28    --   96.67 -68.00  90.00  108
  9  \w     29.00  83.00   0.50    0.28    --   96.67 -68.00  60.00  108
 10  \w     41.00  99.00   0.50    0.20    --   40.33-138.00 -30.00  116
 11  \w     44.00 127.00   0.50    0.28    --   96.67-145.00-111.00  166
 12  \w     30.00  57.00   0.50    0.28    --   96.67 -50.00-120.00   54
 13  \w     29.00  66.00   0.50    0.28    --   96.67 -57.00 -70.00   74
 14  \w     30.00  57.00   0.50    0.28    --   96.67 -50.00 -60.00   54
 15  \w     30.00  57.00   0.50    0.28    --   96.67 -50.00   0.00   54
 16  \w     30.00  57.00   0.50    0.28    --   96.67 -50.00  60.00   54
 17  \w    -26.00  62.00   0.50    0.20    --   40.33 -57.00 -70.00  176
 18  \w    -27.00  63.00   0.50    0.20    --   40.33 -63.00 119.00  180
 19  \w    105.00 170.00   0.50    0.28    --   96.67  96.00 120.00  130
 20  \w     94.00 163.00   0.50    0.28    --   96.67 126.00 132.00  138
 21  \w     14.00 109.00   0.50    0.20    --   40.33  77.00 -30.00  190
 22  \w     18.00 108.00   0.50    0.20    --   40.33  63.00-103.00  180
 23  \w     78.00 163.00   0.50    0.28    --   96.67  50.00-180.00  170
 24  \w     74.00 164.00   0.50    0.28    --   96.67  63.00-103.00  180
 25  \w     76.00 164.00   0.50    0.28    --   96.67  57.00  71.00  176
 26  \w    -74.00 -14.00   0.50    0.28    --  -82.50  63.00-103.00  120
 27  \w    -66.00 -14.00   0.50    0.28    --  -82.50  57.00  71.00  104
 28  \w    -56.00 -16.00   0.50    0.28    --  -82.50  50.00 150.00   80
 29  \w   -150.00 -61.00   0.50    0.28    --  -82.50 -57.00 -70.00  178
 30  \w   -108.00 -59.00   0.50    0.20    --  -40.33-145.00-111.00   98
 31  \w   -151.00 -59.00   0.50    0.28    --  -82.50 -63.00 119.00  184
 32  \w   -106.00 -25.00   0.50    0.20    --  -40.33 -38.00 150.00  162
 33  \w   -109.00 -13.00   0.50    0.20    --  -40.33 -77.00  30.00  192
 34  \w   -109.00 -13.00   0.50    0.20    --  -40.33 -77.00   0.00  192
 35  \w   -109.00 -13.00   0.50    0.20    --  -40.33 -77.00  60.00  192
 36  \w   -109.00 -13.00   0.50    0.20    --  -40.33 -77.00-120.00  192
 37  \w   -109.00 -13.00   0.50    0.20    --  -40.33 -77.00-180.00  192
 38  \w   -109.00 -13.00   0.50    0.20    --  -40.33 -77.00 -90.00  192
 39  \w   -109.00 -13.00   0.50    0.20    --  -40.33 -77.00  90.00  192
 40  \w   -109.00 -13.00   0.50    0.20    --  -40.33 -77.00 150.00  192
 41  \w   -108.00 -17.00   0.50    0.20    --  -40.33 -63.00 119.00  182
 42  \w   -107.00 -19.00   0.50    0.20    --  -40.33 -57.00 -70.00  176
 43  \w    -87.00 -12.00   0.50    0.20    --  -40.33 126.00 132.00  150
 44  \w    -88.00 -16.00   0.50    0.28    --  -82.50 126.00 132.00  144
;
_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      0.0172319000
_diffrn_orient_matrix_UB_12      -0.0499865000
_diffrn_orient_matrix_UB_13      -0.0436111000
_diffrn_orient_matrix_UB_21      -0.2255979000
_diffrn_orient_matrix_UB_22      -0.0005535000
_diffrn_orient_matrix_UB_23      -0.0058769000
_diffrn_orient_matrix_UB_31      0.0138672000
_diffrn_orient_matrix_UB_32      0.0534104000
_diffrn_orient_matrix_UB_33      -0.0410227000
_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  0.1162
_diffrn_reflns_av_unetI/netI     0.0436
_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       -8
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            38876
_diffrn_reflns_point_group_measured_fraction_full 0.927
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.303
_diffrn_reflns_theta_min         2.717
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.615
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78866
_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 light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_description       block
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details
;
 Flack x determined using 2156 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.07(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     475
_refine_ls_number_reflns         6176
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0405
_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^)+(0.0662P)^2^+0.2503P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1041
_refine_ls_wR_factor_ref         0.1058
_reflns_Friedel_coverage         0.624
_reflns_Friedel_fraction_full    0.832
_reflns_Friedel_fraction_max     0.822
_reflns_number_gt                5879
_reflns_number_total             6176
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc04103h3.cif
_cod_data_source_block           sk_0283a_ayan
_cod_depositor_comments
;

2025-06-02
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C42 H52 O6'
_cod_original_formula_weight         652.83
_cod_original_formula_moiety         '2(C21 H26 O3)'
_cod_original_formula_units_Z            4
_cod_database_code               1572168
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O'
_chemical_oxdiff_usercomment     100K
_shelx_estimated_absorpt_t_max   0.856
_shelx_estimated_absorpt_t_min   0.732
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C00N(H00W), C00P(H00P), C010(H010), C012(H012), C014(H014), C016(H016)
2.b Secondary CH2 refined with riding coordinates:
 C00G(H00Q,H00R), C00Q(H00D,H00E), C00V(H00X,H00Y), C00Z(H00I,H00J)
2.c Aromatic/amide H refined with riding coordinates:
 C007(H007), C00E(H00N), C00I(H00S), C00O(H00O)
2.d Idealised Me refined as rotating group:
 C00D(H00K,H00L,H00M), C00L(H00T,H00U,H00V), C00M(H00A,H00B,H00C), C00U(H00F,
 H00G,H00H), C018(H01M,H01N,H01O), C019(H01E,H01F,H01G), C01B(H01P,H01Q,H01R),
 C01C(H01H,H01I,H01J)
2.e Idealised tetrahedral OH refined as rotating group:
 O002(H002), O005(H005)
;
_shelx_res_checksum              63419
_shelx_hkl_checksum              23595
_olex2_submission_original_sample_id AB_SK0283A
_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 1.251
_oxdiff_exptl_absorpt_empirical_full_min 0.820