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

data_7158550
_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         'C22 H29 N O5'
_chemical_formula_sum            'C22 H29 N O5'
_chemical_formula_weight         387.46
_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   geom
_audit_creation_date             2021-08-25
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.9706(8)
_cell_length_b                   8.0539(8)
_cell_length_c                   42.817(5)
_cell_measurement_reflns_used    4687
_cell_measurement_temperature    150.0(1)
_cell_measurement_theta_max      76.1720
_cell_measurement_theta_min      4.1080
_cell_volume                     2058.9(4)
_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  'ShelXL (Sheldrick, 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 0.996
_diffrn_measured_fraction_theta_max 0.978
_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   -112.00 -84.00   0.50    2.30    --  -49.67-132.00 167.00   56
  2  \w   -109.00 -77.00   0.50    2.30    --  -49.67-137.00  -9.00   64
  3  \w    -43.00 -18.00   0.50    9.00    --  -84.25  18.00  19.00   50
  4  \w     99.00 154.00   0.50    9.00    --  105.75  18.00  19.00  110
  5  \w    105.00 145.00   0.50    9.00    --  105.75 132.00-123.00   80
  6  \w    137.00 167.00   0.50    9.00    --  105.75 107.00 160.00   60
  7  \w   -119.00 -88.00   0.50    2.30    --  -49.67 -77.00-180.00   62
  8  \w    -42.00  24.00   0.50    2.30    --  -49.67  19.00 120.00  132
  9  \w    -69.00 -42.00   0.50    9.00    --  -84.25  61.00-180.00   54
 10  \w     38.00  66.00   0.50    9.00    --  105.75 -61.00 150.00   56
 11  \w     35.00  65.00   0.50    9.00    --  105.75 -94.00 -60.00   60
 12  \w     94.00 163.00   0.50    9.00    --  105.75  61.00 -60.00  138
 13  \w     35.00  70.00   0.50    9.00    --  105.75 -94.00  30.00   70
 14  \w     77.00 106.00   0.50    9.00    --  105.75 -94.00  90.00   58
 15  \w     38.00  68.00   0.50    9.00    --  105.75 -77.00-120.00   60
 16  \w     57.00  91.00   0.50    9.00    --  105.75 -94.00  60.00   68
 17  \w     76.00 109.00   0.50    9.00    --  105.75-125.00 150.00   66
 18  \w     58.00  83.00   0.50    9.00    --  105.75 -94.00-180.00   50
 19  \w     79.00 104.00   0.50    9.00    --  105.75 -94.00 -60.00   50
 20  \w     74.00 106.00   0.50    9.00    --  105.75 -94.00 120.00   64
 21  \w     34.00  59.00   0.50    9.00    --  105.75 -61.00-120.00   50
 22  \w     43.00  68.00   0.50    9.00    --  105.75 -61.00 120.00   50
;
_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      -0.2391477000
_diffrn_orient_matrix_UB_12      0.0194659000
_diffrn_orient_matrix_UB_13      0.0128617000
_diffrn_orient_matrix_UB_21      -0.0954479000
_diffrn_orient_matrix_UB_22      -0.0415219000
_diffrn_orient_matrix_UB_23      -0.0325431000
_diffrn_orient_matrix_UB_31      -0.0038965000
_diffrn_orient_matrix_UB_32      -0.1857898000
_diffrn_orient_matrix_UB_33      0.0086051000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0853
_diffrn_reflns_av_unetI/netI     0.0756
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       52
_diffrn_reflns_limit_l_min       -53
_diffrn_reflns_number            10856
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.791
_diffrn_reflns_theta_min         4.130
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.717
_exptl_absorpt_correction_T_max  0.98016
_exptl_absorpt_correction_T_min  0.83177
_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    1.250
_exptl_crystal_description       Plate
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details
;
 Flack x determined using 1015 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         4065
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0980
_refine_ls_R_factor_gt           0.0789
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0358P)^2^+5.6251P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1769
_refine_ls_wR_factor_ref         0.1965
_reflns_Friedel_coverage         0.604
_reflns_Friedel_fraction_full    0.915
_reflns_Friedel_fraction_max     0.846
_reflns_number_gt                3456
_reflns_number_total             4065
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00238h2.cif
_cod_data_source_block           gs649
_cod_database_code               7158550
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C88 H116 N4 O20'
_chemical_oxdiff_usercomment     'from Georgijs'
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.858
_diffrn_oxdiff_digest_frames
;
01745e29ae5ed7d8777be269ae89f47c2d00027780a
;
_diffrn_oxdiff_digest_hkl
;
01c67ddcf113d6d853a4fa2075a55bc5a4e8ba
;
_reflns_odcompleteness_completeness 97.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     77.49
_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), C9(H9), C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C6(H6A,H6B), C10(H10A,H10B), C3(H3A,H3B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C25(H25), C21(H21), C24(H24), C22(H22)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C16(H16A,H16B,H16C), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C)
;
_shelx_res_checksum              35808
_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 2.169
_oxdiff_exptl_absorpt_empirical_full_min 0.374