Teotihuacanin, a Diterpene with an Unusual Spiro-10/6 System from Salvia amarissima with Potent Modulatory Activity of Multidrug Resistance in Cancer Cells.
Bautista, Elihú; Fragoso-Serrano, Mabel; Toscano, Rubén A; García-Peña, María Del Rosario; Ortega, Alfredo; Organic letters 17 (2015) 3280–3282; doi:10.1021/acs.orglett.5b01320

data_1520577
_publ_section_title
;
 Teotihuacanin, a Diterpene with an Unusual Spiro-10/6 System from Salvia
 amarissima with Potent Modulatory Activity of Multidrug Resistance in
 Cancer Cells.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3280
_journal_page_last               3282
_journal_paper_doi               10.1021/acs.orglett.5b01320
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H20 O6'
_chemical_formula_sum            'C20 H20 O6'
_chemical_formula_weight         356.36
_chemical_name_common            Teotihuacanin
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1756(4)
_cell_length_b                   12.2477(5)
_cell_length_c                   13.4918(6)
_cell_measurement_reflns_used    9870
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      74.37
_cell_measurement_theta_min      3.28
_cell_volume                     1681.45(12)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2012 (Bruker, 2013)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture \k-geometry diffractometer'
_diffrn_measurement_method       \w-scans
_diffrn_radiation_monochromator  'Helios multilayer mirror'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            19472
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.476
_diffrn_reflns_theta_min         4.876
_diffrn_source                   'micro-focus X-ray source'
_exptl_absorpt_coefficient_mu    0.865
_exptl_absorpt_correction_T_max  0.9364
_exptl_absorpt_correction_T_min  0.9079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Sheldrick, 2012)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_description       prism
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.114
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.077
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.134
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;

 Flack x determined using 1064 quotients [(I+)-(I-)]/[(I+)+(I-)]

 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).

;
_refine_ls_abs_structure_Flack   -0.09(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3428
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0421
_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^)+(0.0543P)^2^+0.1836P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1006
_refine_ls_wR_factor_ref         0.1066
_reflns_Friedel_coverage         0.745
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                2899
_reflns_number_total             3428
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b01320_si_002.cif
_cod_data_source_block           050OHA15
_cod_depositor_comments          'Adding full bibliography for 1520577.cif.'
_cod_database_code               1520577
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.908
_shelx_estimated_absorpt_t_max   0.936
_shelx_res_checksum              2929
_shelx_hkl_checksum              88718