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_1517486
_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 ad
_chemical_formula_sum            'C33 H34 Br2 O8'
_chemical_formula_weight         718.42
_chemical_name_systematic
;

 (R)-4-((2R,3aR,4'S,5'S,6aS,E)-4'-((4-bromobenzoyl)oxy)-4-
((R)-5-methyldihydrofuran-2(3H)-ylidene)-5-oxooctahydro-
3'H-spiro[cyclopenta[b]furan-2,2'-furan]-5'-yl)butan-2-yl 4-bromobenzoate

;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 106.780(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   15.188(5)
_cell_length_b                   5.728(2)
_cell_length_c                   18.462(7)
_cell_measurement_reflns_used    4336
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.45
_cell_measurement_theta_min      2.30
_cell_volume                     1537.7(9)
_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    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.898
_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  0.0298
_diffrn_reflns_av_unetI/netI     0.0691
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.898
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8879
_diffrn_reflns_point_group_measured_fraction_full 0.896
_diffrn_reflns_point_group_measured_fraction_max 0.774
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.714
_diffrn_reflns_theta_min         1.152
_diffrn_source                   'rotating anode'
_exptl_absorpt_coefficient_mu    2.687
_exptl_absorpt_correction_T_max  0.9482
_exptl_absorpt_correction_T_min  0.6155
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             732
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.660
_refine_diff_density_min         -1.043
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details
;
 Flack x determined using 1628 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.005(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     390
_refine_ls_number_reflns         6172
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.983
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0486
_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^)+(0.0697P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1169
_refine_ls_wR_factor_ref         0.1213
_reflns_Friedel_coverage         0.573
_reflns_Friedel_fraction_full    0.776
_reflns_Friedel_fraction_max     0.625
_reflns_number_gt                4971
_reflns_number_total             6172
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol502216j_si_003.cif
_cod_data_source_block           p2Bz2
_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_original_cell_volume        1537.7(10)
_cod_database_code               1517486
_shelx_estimated_absorpt_t_min   0.616
_shelx_estimated_absorpt_t_max   0.948
_shelxl_version_number           2014-3
_shelx_res_checksum              78873
_shelx_hkl_checksum              89378