Semisynthesis and absolute configuration of a novel rearranged 19,20-δ-lactone (9βH)-pimarane diterpene
Brito, Maria V.; Marques, Ricardo A.; Mattos, Marcos C.; Alvarenga, Meiry E.; Valdo, Ana Karoline S. M.; Oliveira, Maria C. F.; Martins, Felipe T.; Acta Crystallographica Section C Structural Chemistry 74 (2018) –; doi:10.1107/S2053229618009452

data_2021173
_publ_section_title
;
 Semisynthesis and absolute configuration of a novel rearranged
 19,20-\d-lactone (9\bH)-pimarane diterpene
;
_journal_coeditor_code           QS3074
_journal_issue                   8
_journal_name_full
'Acta Crystallographica Section C Structural Chemistry'
_journal_paper_doi               10.1107/S2053229618009452
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C20 H30 O6, H2 O'
_chemical_formula_moiety         'C20 H30 O6, H2 O'
_chemical_formula_sum            'C20 H32 O7'
_chemical_formula_weight         384.45
_chemical_name_common
;
3\b,6\b,16-Trihydroxy-7-pimaren-19,20\b-olide monohydrate
;
_chemical_name_systematic
;
5-(1,2-Dihydroxyethyl]-9,17-dihydroxy-5,11-dimethyl-13-\
oxatetracyclo[9.3.3.0^1,10^.0^2,7^]heptadec-7-en-12-one monohydrate
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.7555(14)
_cell_length_b                   20.224(2)
_cell_length_c                   8.0385(11)
_cell_measurement_reflns_used    3033
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      67.60
_cell_measurement_theta_min      4.372
_cell_volume                     1911.1(4)
_computing_cell_refinement
;
SAINT (Bruker, 2003)
;
_computing_data_collection
;
APEX2 (Bruker, 2003)
;
_computing_data_reduction
;
SAINT (Bruker, 2003)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae <i>et al</i>.,
2008)
;
_computing_publication_material
;
WinGX (Farrugia, 2012)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SIR92 (Altomare <i>et al</i>.,  1993)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       CCD
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9565
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.189
_diffrn_reflns_theta_min         4.35
_exptl_absorpt_coefficient_mu    0.826
_exptl_absorpt_correction_T_max  0.921
_exptl_absorpt_correction_T_min  0.737
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause <i>et al.</i>,  2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_description       prism
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.245
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 917 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   -0.01(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         3311
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0455
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0845P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1222
_refine_ls_wR_factor_ref         0.1369
_reflns_number_gt                2594
_reflns_number_total             3311
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            qs3074sup1.cif
_cod_data_source_block           compound_4a
_cod_database_code               2021173
_cod_database_fobs_code          2021173
_shelx_hkl_checksum              1757
_shelx_res_checksum              63765
_shelxl_version_number           2.014