Opaliferin, a New Polyketide from Cultures of Entomopathogenic Fungus Cordyceps sp. NBRC 106954.
Grudniewska, Aleksandra; Hayashi, Sayaka; Shimizu, Mina; Kato, Masayuki; Suenaga, Midori; Imagawa, Hiroshi; Ito, Takuya; Asakawa, Yoshinori; Ban, Sayaka; Kumada, Toshio; Hashimoto, Toshihiro; Umeyama, Akemi; Organic letters 16 (2014) 4695–4697; doi:10.1021/ol502216j

data_1517485
_publ_section_title
;
 Opaliferin, a New Polyketide from Cultures of Entomopathogenic Fungus
 Cordyceps sp. NBRC 106954.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4695
_journal_page_last               4697
_journal_paper_doi               10.1021/ol502216j
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration rm
_chemical_formula_sum            'C19 H28 O6'
_chemical_formula_weight         352.41
_chemical_name_systematic
;
 (2R*,3aR*,4'S*,5'S*,6aS*,E)-4'-hydroxy-5'-((R*)-3-hydroxybutyl)-
4-((R*)-5-methyldihydrofuran-2(3H)-ylidene)hexahydro-
3'H-spiro[cyclopenta[b]furan-2,2'-furan]-5(3H)-one
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 92.513(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.5715(11)
_cell_length_b                   8.0680(16)
_cell_length_c                   20.262(4)
_cell_measurement_reflns_used    4809
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.61
_cell_measurement_theta_min      2.72
_cell_volume                     909.9(3)
_computing_cell_refinement       'Bruker  APEX2'
_computing_data_collection       'Bruker  APEX2'
_computing_data_reduction        'Bruker  APEX2'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'multilayered conforcal mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4392
_diffrn_reflns_point_group_measured_fraction_full 0.920
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_min         2.012
_diffrn_source                   'rotating anode'
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.9813
_exptl_absorpt_correction_T_min  0.9721
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 1212 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.263
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     338
_refine_ls_number_reflns         2968
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.263
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.0302
_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^)+(0.0589P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0857
_refine_ls_wR_factor_ref         0.0862
_reflns_Friedel_coverage         0.717
_reflns_Friedel_fraction_full    0.833
_reflns_Friedel_fraction_max     0.833
_reflns_number_gt                2924
_reflns_number_total             2968
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol502216j_si_002.cif
_cod_data_source_block           newP2
_cod_depositor_comments
;Adding full bibliography for 1517485--1517486.cif.

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               1517485
_shelx_estimated_absorpt_t_min   0.972
_shelx_estimated_absorpt_t_max   0.981
_shelxl_version_number           2014-3
_shelx_res_checksum              15220
_shelx_hkl_checksum              42936