A Concise Bioinspired Semisynthesis of Rumphellaones A-C and Their C-8 Epimers from β-Caryophyllene.
Stakanovs, Georgijs; Mishnev, Anatoly; Rasina, Dace; Jirgensons, Aigars; Journal of natural products 83 (2020) 2004–2009; doi:10.1021/acs.jnatprod.0c00403

data_1558318
_publ_section_title
;
 A Concise Bioinspired Semisynthesis of Rumphellaones A-C and Their C-8
 Epimers from \b-Caryophyllene.
;
_journal_issue                   6
_journal_name_full               'Journal of natural products'
_journal_page_first              2004
_journal_page_last               2009
_journal_paper_doi               10.1021/acs.jnatprod.0c00403
_journal_volume                  83
_journal_year                    2020
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C22 H27 N O7'
_chemical_formula_sum            'C22 H27 N O7'
_chemical_formula_weight         417.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
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_cell_angle_beta                 102.7500(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.7540(2)
_cell_length_b                   9.07510(10)
_cell_length_c                   26.1928(3)
_cell_measurement_reflns_used    30997
_cell_measurement_temperature    160(2)
_cell_measurement_theta_max      75.8960
_cell_measurement_theta_min      3.2510
_cell_volume                     4347.95(8)
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      160(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            42816
_diffrn_reflns_point_group_measured_fraction_full 0.817
_diffrn_reflns_point_group_measured_fraction_max 0.753
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.149
_diffrn_reflns_theta_min         2.642
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.791
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73670
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.74a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_description       block
_exptl_crystal_F_000             1776
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.673
_refine_diff_density_min         -0.553
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 4207 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1090
_refine_ls_number_reflns         14036
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0563
_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^)+(0.1007P)^2^+2.7967P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1695
_refine_ls_wR_factor_ref         0.1765
_reflns_Friedel_coverage         0.500
_reflns_Friedel_fraction_full    0.610
_reflns_Friedel_fraction_max     0.537
_reflns_number_gt                13218
_reflns_number_total             14036
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np0c00403_si_003.cif
_cod_data_source_block           gs_392c
_cod_depositor_comments
'Adding full bibliography for 1558318--1558319.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1558318
_shelx_shelxl_version_number     2017/1
_shelx_res_checksum              85184
_shelx_hkl_checksum              5867