Microphyllandiolide, a new diterpene with an unprecedented skeleton from Salvia microphylla.
Bautista, Elihú; Toscano, Rubén Alfredo; Ortega, Alfredo; Organic letters 15 (2013) 3210–3213; doi:10.1021/ol401022c

data_1556158
_publ_section_title
;
 Microphyllandiolide, a new diterpene with an unprecedented skeleton from
 Salvia microphylla.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3210
_journal_page_last               3213
_journal_paper_doi               10.1021/ol401022c
_journal_volume                  15
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H20 O6'
_chemical_formula_sum            'C20 H20 O6'
_chemical_formula_weight         356.36
_chemical_name_common            Mycrophyllandiolide
_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
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.0241(4)
_cell_length_b                   10.2749(4)
_cell_length_c                   16.6432(6)
_cell_measurement_reflns_used    9979
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      66.79
_cell_measurement_theta_min      4.30
_cell_volume                     1714.19(11)
_computing_cell_refinement       'Bruker APEX2'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'SHELXTL V 6.12 (Sheldrick, 2000)'
_computing_publication_material  'SHELXTL V 6.12 (Sheldrick, 2000)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'micro-focus X-ray source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_unetI/netI     0.0065
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            62160
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.787
_diffrn_reflns_theta_min         5.151
_exptl_absorpt_coefficient_mu    0.848
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6863
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_description       prism
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.426
_exptl_crystal_size_mid          0.252
_exptl_crystal_size_min          0.192
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 1273 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.018(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         3020
_refine_ls_number_restraints     108
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0308
_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^)+(0.0629P)^2^+0.1469P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0922
_refine_ls_wR_factor_ref         0.0923
_reflns_Friedel_coverage         0.735
_reflns_Friedel_fraction_full    0.973
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                3003
_reflns_number_total             3020
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol401022c_si_002.cif
_cod_data_source_block           Compound_1
_cod_database_code               1556158
_shelx_estimated_absorpt_t_min   0.714
_shelx_estimated_absorpt_t_max   0.854
_shelxl_version_number           2013-2
_shelx_res_checksum              81577