Convergent Biomimetic Semisynthesis of Disesquiterpenoid Rumphellolide J
Stakanovs, Georgijs; Belyakov, Sergey; Jirgensons, Aigars; Rasina, Dace; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB00238H

data_7158552
_publ_section_title
;
 Convergent Biomimetic Semisynthesis of Disesquiterpenoid Rumphellolide J
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB00238H
_journal_year                    2022
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C15 H24 O2'
_chemical_formula_sum            'C15 H24 O2'
_chemical_formula_weight         236.36
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_Int_Tables_number      1
_audit_creation_date             2021-10-21
_audit_creation_method
;
Olex2 1.2-ac4
(compiled 2018.05.17 svn.r3504 for Rigaku Oxford Diffraction, GUI svn.r5492)
;
_audit_update_record
;
2021-12-09 deposited with the CCDC.	2022-03-02 downloaded from the CCDC.
;
_cell_angle_alpha                102.879(2)
_cell_angle_beta                 100.4135(17)
_cell_angle_gamma                102.0461(16)
_cell_formula_units_Z            6
_cell_length_a                   9.17564(16)
_cell_length_b                   15.1486(3)
_cell_length_c                   16.0961(4)
_cell_measurement_reflns_used    18032
_cell_measurement_temperature    150.0(1)
_cell_measurement_theta_max      76.7810
_cell_measurement_theta_min      3.0910
_cell_volume                     2071.52(8)
_computing_cell_refinement       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.0(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.97
_diffrn_measured_fraction_theta_max 0.6729
_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    -51.00  23.00   0.50    2.00    --  -47.65  88.00-150.00  148
  2  \w    -11.00  71.00   0.50    2.00    --   47.65 -88.00  92.00  164
  3  \w    -88.00 -63.00   0.50    9.00    --  -86.25  88.00-150.00   50
  4  \w   -143.00-118.00   0.50    9.00    --  -86.25 -88.00  92.00   50
  5  \w    119.00 150.00   0.50    9.00    --  107.75  88.00-150.00   62
  6  \w     96.00 123.00   0.50    9.00    --  107.75 -88.00  92.00   54
  7  \w   -109.00 -82.00   0.50    2.00    --  -47.65-125.00-180.00   54
  8  \w   -119.00 -94.00   0.50    2.00    --  -47.65 -77.00   0.00   50
  9  \w   -119.00 -94.00   0.50    2.00    --  -47.65 -77.00 -60.00   50
 10  \w   -114.00 -89.00   0.50    2.00    --  -47.65 -77.00-150.00   50
 11  \w   -119.00 -94.00   0.50    2.00    --  -47.65 -77.00 -90.00   50
 12  \w    -25.00  10.00   0.50    2.00    --   47.65 -19.00  60.00   70
 13  \w     56.00  82.00   0.50    2.00    --   47.65-125.00-180.00   52
 14  \w    -20.00  35.00   0.50    2.00    --   47.65 -19.00-180.00  110
 15  \w     88.00 117.00   0.50    2.00    --   47.65  77.00 150.00   58
 16  \w     14.00  39.00   0.50    2.00    --   47.65 -19.00  60.00   50
 17  \w     49.00  95.00   0.50    2.00    --   47.65-125.00 -60.00   92
 18  \w     89.00 120.00   0.50    2.00    --   47.65  77.00-180.00   62
 19  \w     88.00 120.00   0.50    2.00    --   47.65  77.00  90.00   64
 20  \w    -42.00 -12.00   0.50    9.00    --  -86.25  30.00  60.00   60
 21  \w    102.00 134.00   0.50    9.00    --  107.75 -88.00-119.54   64
 22  \w     46.00  72.00   0.50    9.00    --  107.75 -88.00-119.54   52
 23  \w     95.00 165.00   0.50    9.00    --  107.75  15.00  30.00  140
 24  \w     37.00  91.00   0.50    9.00    --  107.75 -94.00-120.00  108
 25  \w     58.00 107.00   0.50    9.00    --  107.75-107.00 -87.07   98
 26  \w     66.00 118.00   0.50    9.00    --  107.75 -88.00-166.41  104
 27  \w     60.00 106.00   0.50    9.00    --  107.75 -97.00 -26.84   92
 28  \w    125.00 151.00   0.50    9.00    --  107.75  61.00 150.00   52
 29  \w    107.00 133.00   0.50    9.00    --  107.75 -85.00   9.01   52
 30  \w     77.00 107.00   0.50    9.00    --  107.75-102.00 177.41   60
 31  \w     38.00  64.00   0.50    9.00    --  107.75 -88.00 -42.04   52
 32  \w     97.00 123.00   0.50    9.00    --  107.75 125.00  90.00   52
 33  \w    140.00 171.00   0.50    9.00    --  107.75 125.00  90.00   62
 34  \w     45.00  73.00   0.50    9.00    --  107.75 -77.00  90.00   56
 35  \w    125.00 152.00   0.50    9.00    --  107.75  77.00   0.00   54
 36  \w    106.00 134.00   0.50    9.00    --  107.75  15.00 -30.00   56
 37  \w     39.00  87.00   0.50    9.00    --  107.75 -77.00 120.00   96
 38  \w     48.00  73.00   0.50    9.00    --  107.75 -85.00   9.01   50
 39  \w     36.00  63.00   0.50    9.00    --  107.75 -61.00 -90.00   54
 40  \w     65.00 106.00   0.50    9.00    --  107.75 -94.00  30.00   82
 41  \w     42.00  68.00   0.50    9.00    --  107.75 -77.00  30.00   52
 42  \w     80.00 105.00   0.50    9.00    --  107.75 -94.00   0.00   50
 43  \w     36.00  63.00   0.50    9.00    --  107.75 -94.00   0.00   54
 44  \w     36.00  67.00   0.50    9.00    --  107.75 -61.00  30.00   62
 45  \w     36.00  61.00   0.50    9.00    --  107.75 -77.00-150.00   50
 46  \w     68.00 106.00   0.50    9.00    --  107.75 -94.00 -60.00   76
 47  \w    144.00 171.00   0.50    9.00    --  107.75  77.00-120.00   54
 48  \w    124.00 178.00   0.50    9.00    --  107.75  30.00  90.00  108
 49  \w     71.00 107.00   0.50    9.00    --  107.75-105.00 152.13   72
 50  \w     93.00 118.00   0.50    9.00    --  107.75  61.00 150.00   50
 51  \w     63.00 104.00   0.50    9.00    --  107.75 -94.00  90.00   82
 52  \w     59.00  92.00   0.50    9.00    --  107.75-125.00-120.00   66
 53  \w     37.00  62.00   0.50    9.00    --  107.75 -85.00  -2.36   50
 54  \w    120.00 146.00   0.50    9.00    --  107.75  77.00 150.00   52
 55  \w     36.00  62.00   0.50    9.00    --  107.75 -61.00  60.00   52
 56  \w     59.00  84.00   0.50    9.00    --  107.75 -77.00 -30.00   50
 57  \w    153.00 178.00   0.50    9.00    --  107.75  45.00-180.00   50
 58  \w     81.00 106.00   0.50    9.00    --  107.75 -94.00-180.00   50
 59  \w    107.00 132.00   0.50    9.00    --  107.75 -88.00 -42.04   50
 60  \w    109.00 177.00   0.50    9.00    --  107.75 125.00  30.00  136
 61  \w    127.00 174.00   0.50    9.00    --  107.75  45.00 120.00   94
 62  \w     59.00  89.00   0.50    9.00    --  107.75 -94.00  60.00   60
 63  \w     89.00 134.00   0.50    9.00    --  107.75  77.00 -60.00   90
 64  \w    147.00 177.00   0.50    9.00    --  107.75  77.00 -60.00   60
 65  \w     41.00  73.00   0.50    9.00    --  107.75 -94.00-180.00   64
 66  \w     89.00 114.00   0.50    9.00    --  107.75  77.00  60.00   50
 67  \w    141.00 166.00   0.50    9.00    --  107.75  77.00  60.00   50
 68  \w     97.00 133.00   0.50    9.00    --  107.75  45.00-180.00   72
 69  \w     36.00  70.00   0.50    9.00    --  107.75-125.00 -90.00   68
 70  \w     67.00  93.00   0.50    9.00    --  107.75 -94.00 120.00   52
 71  \w     57.00  91.00   0.50    9.00    --  107.75 -77.00 -90.00   68
 72  \w     35.00  63.00   0.50    9.00    --  107.75 -61.00   0.00   56
 73  \w     71.00  96.00   0.50    9.00    --  107.75-125.00 120.00   50
 74  \w    126.00 153.00   0.50    9.00    --  107.75  30.00-180.00   54
 75  \w     90.00 127.00   0.50    9.00    --  107.75  77.00  90.00   74
 76  \w     88.00 114.00   0.50    9.00    --  107.75  77.00 150.00   52
 77  \w    153.00 178.00   0.50    9.00    --  107.75  15.00 -30.00   50
 78  \w    103.00 128.00   0.50    9.00    --  107.75  30.00 120.00   50
 79  \w     90.00 115.00   0.50    9.00    --  107.75 -85.00  -2.36   50
 80  \w     99.00 177.00   0.50    9.00    --  107.75  30.00 -90.00  156
 81  \w     87.00 112.00   0.50    9.00    --  107.75-125.00 -30.00   50
 82  \w     36.00  61.00   0.50    9.00    --  107.75-125.00  60.00   50
 83  \w     38.00  65.00   0.50    9.00    --  107.75-125.00  90.00   54
 84  \w    105.00 141.00   0.50    9.00    --  107.75  88.00-145.06   72
 85  \w    151.00 178.00   0.50    9.00    --  107.75  45.00-150.00   54
 86  \w    108.00 176.00   0.50    9.00    --  107.75  30.00-150.00  136
 87  \w    106.00 131.00   0.50    9.00    --  107.75  15.00 150.00   50
 88  \w     94.00 119.00   0.50    9.00    --  107.75  77.00-120.00   50
 89  \w     36.00  61.00   0.50    9.00    --  107.75 -61.00-180.00   50
 90  \w    110.00 142.00   0.50    9.00    --  107.75  61.00 -60.00   64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku, XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0627055000
_diffrn_orient_matrix_UB_12      -0.0377455000
_diffrn_orient_matrix_UB_13      -0.0795137000
_diffrn_orient_matrix_UB_21      0.0503466000
_diffrn_orient_matrix_UB_22      -0.0731699000
_diffrn_orient_matrix_UB_23      0.0434392000
_diffrn_orient_matrix_UB_31      -0.1574231000
_diffrn_orient_matrix_UB_32      -0.0699375000
_diffrn_orient_matrix_UB_33      -0.0448408000
_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  0.0562
_diffrn_reflns_av_unetI/netI     0.0503
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            37044
_diffrn_reflns_theta_full        73.0
_diffrn_reflns_theta_max         77.48
_diffrn_reflns_theta_min         2.90
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.571
_exptl_absorpt_correction_T_max  0.99806
_exptl_absorpt_correction_T_min  0.94198
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'Colourless '
_exptl_crystal_density_diffrn    1.1367
_exptl_crystal_description       Needle
_exptl_crystal_F_000             780
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.6185
_refine_diff_density_min         -0.2107
_refine_diff_density_rms         0.0441
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_d_res_high            0.7897
_refine_ls_d_res_low             15.2388
_refine_ls_goodness_of_fit_ref   1.0570
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    204
_refine_ls_number_parameters     961
_refine_ls_number_reflns         11863
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.0570
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0680
_refine_ls_shift/su_max          0.0046
_refine_ls_shift/su_mean         0.0013
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1031P)^2^+0.8797P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1748
_refine_ls_wR_factor_ref         0.1790
_reflns_Friedel_coverage         0.374
_reflns_limit_h_max              10
_reflns_limit_h_min              -11
_reflns_limit_k_max              19
_reflns_limit_k_min              -19
_reflns_limit_l_max              20
_reflns_limit_l_min              -20
_reflns_number_gt                10849
_reflns_number_total             11863
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d2ob00238h2.cif
_cod_data_source_block           GS672
_cod_depositor_comments
;

2024-12-16
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C90 H144 O12'
_cod_original_formula_weight         1418.14
_cod_original_formula_moiety         '6(C15 H24 O2)'
_cod_original_formula_units_Z            1
_cod_original_cell_volume        2071.53(8)
_cod_original_sg_symbol_Hall     ' P 1'
_cod_database_code               7158552
_chemical_oxdiff_formula         'C90 H144 O12'
_chemical_oxdiff_usercomment     'from Georgijs'
_diffrn_oxdiff_digest_frames
;
0150f4ac4f7ff7e0e91eb444dc10ef61cd00026213c
;
_diffrn_oxdiff_digest_hkl
;
01e5c07bdab9f82049448a7081a6409fdca8e8
;
_reflns_odcompleteness_completeness 99.47
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C5(H5), C56(H56), C22(H22), C73(H73), C39(H39), C70(H70), C2(H2), C36(H36),
 C87(H87), C19(H19), C53(H53), C90(H90)
2.b Secondary CH2 refined with riding coordinates:
 C28(H28a,H28b), C79(H79a,H79b), C40(H40a,H40b), C60(H60a,H60b), C58(H58a,
 H58b), C62(H62a,H62b), C41(H41a,H41b), C57(H57a,H57b), C74(H74a,H74b),
 C78(H78a,H78b), C43(H43a,H43b), C6(H6a,H6b), C77(H77a,H77b), C26(H26a,H26b),
 C61(H61a,H61b), C3(H3a,H3b), C23(H23a,H23b), C45(H45a,H45b), C54(H54a,H54b),
 C27(H27a,H27b), C71(H71a,H71b), C7(H7a,H7b), C75(H75a,H75b), C24(H24a,H24b),
 C11(H11a,H11b), C10(H10a,H10b), C37(H37a,H37b), C9(H9a,H9b), C44(H44a,H44b),
 C92(H92a,H92b), C20(H20a,H20b), C91(H91a,H91b), C94(H94a,H94b), C95(H95a,H95b),
  C96(H96a,H96b), C88(H88a,H88b)
2.c Idealised Me refined as rotating group:
 C14(H14a,H14b,H14c), C80(H80a,H80b,H80c), C64(H64a,H64b,H64c), C65(H65a,H65b,
 H65c), C13(H13a,H13b,H13c), C99(H99a,H99b,H99c), C48(H48a,H48b,H48c), C63(H63a,
 H63b,H63c), C46(H46a,H46b,H46c), C29(H29a,H29b,H29c), C82(H82a,H82b,H82c),
 C98(H98a,H98b,H98c), C81(H81a,H81b,H81c), C30(H30a,H30b,H30c), C47(H47a,H47b,
 H47c), C12(H12a,H12b,H12c), C31(H31a,H31b,H31c), C97(H97a,H97b,H97c)
;
_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 1.729
_oxdiff_exptl_absorpt_empirical_full_min 0.459