Amarisolide F, an Acylated Diterpenoid Glucoside and Related Terpenoids from Salvia amarissima.
Fragoso-Serrano, Mabel; Ortiz-Pastrana, Naytzé; Luna-Cruz, Norma; Toscano, Rubén A; Alpuche-Solís, Angel G; Ortega, Alfredo; Bautista, Elihú; Journal of natural products 82 (2019) 631–635; doi:10.1021/acs.jnatprod.8b00565

data_1553402
_publ_section_title
;
 Amarisolide F, an Acylated Diterpenoid Glucoside and Related Terpenoids
 from Salvia amarissima.
;
_journal_issue                   3
_journal_name_full               'Journal of natural products'
_journal_page_first              631
_journal_page_last               635
_journal_paper_doi               10.1021/acs.jnatprod.8b00565
_journal_volume                  82
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H24 O8'
_chemical_formula_sum            'C21 H24 O8'
_chemical_formula_weight         404.40
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7873(3)
_cell_length_b                   10.4684(3)
_cell_length_c                   18.7272(6)
_cell_measurement_reflns_used    9597
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      78.10
_cell_measurement_theta_min      4.22
_cell_volume                     1918.74(10)
_computing_cell_refinement       'APEX2 v2014.1-1(Bruker, 2014)'
_computing_data_collection       'APEX2 v2014.1-1(Bruker, 2014)'
_computing_data_reduction        'SAINT V8.34A (Bruker, 2014)'
_computing_molecular_graphics    'XP V 5.1 (Bruker, 1998)'
_computing_publication_material  'CIFTAB V 2013/2 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 52.0833
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Endevor \k-geometry diffractometer'
_diffrn_measurement_method       '\f and \w-scans'
_diffrn_radiation_monochromator  'Helios multilayer mirror'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0675
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            40482
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.332
_diffrn_reflns_theta_min         4.722
_diffrn_source                   'micro-focus X-ray source'
_exptl_absorpt_coefficient_mu    0.904
_exptl_absorpt_correction_T_max  0.7444
_exptl_absorpt_correction_T_min  0.6581
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Sheldrick, 2012)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_description       arrow-head
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.297
_exptl_crystal_size_mid          0.263
_exptl_crystal_size_min          0.168
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 1499 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4082
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0374
_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^)+(0.0484P)^2^+0.3426P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0956
_refine_ls_wR_factor_ref         0.0995
_reflns_Friedel_coverage         0.750
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3739
_reflns_number_total             4082
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np8b00565_si_002.cif
_cod_data_source_block           361OHA16
_cod_database_code               1553402
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.775
_shelx_estimated_absorpt_t_max   0.863
_shelx_res_checksum              37193
_shelx_hkl_checksum              43808