First stereoselective approach for structure revision of nagiol and syntheses of 2,3-dihydroxyferruginol and ferruginol.
Surendran, Sravya; Ramachandran, Arathi; Goreti, Rajendar; Organic & biomolecular chemistry 23 (2025) 6924–6930; doi:10.1039/d5ob00946d

data_7160609
_publ_section_title
;
 First stereoselective approach for structure revision of nagiol and
 syntheses of 2,3-dihydroxyferruginol and ferruginol.
;
_journal_issue                   29
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6924
_journal_page_last               6930
_journal_paper_doi               10.1039/d5ob00946d
_journal_volume                  23
_journal_year                    2025
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C19 H26 O4'
_chemical_formula_sum            'C19 H26 O4'
_chemical_formula_weight         318.40
_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_Hall           'C 2c 2'
_space_group_name_H-M_alt        'C 2 2 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2025-06-07 deposited with the CCDC.	2025-06-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   6.8089(3)
_cell_length_b                   15.0295(6)
_cell_length_c                   35.9980(17)
_cell_measurement_reflns_used    5250
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      26.80
_cell_measurement_theta_min      2.26
_cell_volume                     3683.8(3)
_computing_cell_refinement       'SAINT V8.5.0.27 (Bruker AXS LLC, 2023)'
_computing_data_collection
'Bruker APEX6 v2024.9-0'(Bruker AXS Inc., 2023)'
_computing_data_reduction        'SAINT V8.5.0.27 (Bruker AXS LLC, 2023)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1503)'
_computing_publication_material  'APEX5 v2023.9-0 (Bruker AXS Inc., 2023)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'XT, VERSION 2018/2 (Sheldrick, 2019)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.39
_diffrn_detector_type            'Bruker PHOTON III C14'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Bruker D8 QUEST'
_diffrn_measurement_device_type  'Four-circle Kappa diffractometer'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_limit_l_min       -48
_diffrn_reflns_number            20034
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.297
_diffrn_reflns_theta_min         2.263
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_current           1.406
_diffrn_source_target            Mo
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.148
_exptl_crystal_density_meas      1.148
_exptl_crystal_density_method    NONE
_exptl_crystal_description       plate
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.152
_exptl_crystal_size_min          0.025
_refine_diff_density_max         0.584
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 1274 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         4542
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0536
_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^)+(0.0915P)^2^+0.6007P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1496
_refine_ls_wR_factor_ref         0.1631
_reflns_Friedel_coverage         0.770
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3572
_reflns_number_total             4542
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00946d2.cif
_cod_data_source_block           shelx
_cod_depositor_comments          'Adding full bibliography for 7160609.cif.'
_cod_database_code               7160609
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_min   0.973
_shelx_estimated_absorpt_t_max   0.998
_computing_bruker_data_scaling
'SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction'
_shelx_res_checksum              60304
_shelx_fab_checksum              41484