Phomanolides C-F from a Phoma sp.: Meroterpenoids Generated via Hetero-Diels-Alder Reactions.
Zhang, Jinyu; Li, Yumei; Ren, Fengxia; Zhang, Yang; Liu, Xingzhong; Liu, Ling; Che, Yongsheng; Journal of natural products 82 (2019) 1678–1685; doi:10.1021/acs.jnatprod.9b00281

data_1552667
_publ_section_title
;
 Phomanolides C-F from a Phoma sp.: Meroterpenoids Generated via
 Hetero-Diels-Alder Reactions.
;
_journal_issue                   6
_journal_name_full               'Journal of natural products'
_journal_page_first              1678
_journal_page_last               1685
_journal_paper_doi               10.1021/acs.jnatprod.9b00281
_journal_volume                  82
_journal_year                    2019
_chemical_formula_moiety         'C32 H40 O8, C H4 O'
_chemical_formula_sum            'C33 H44 O9'
_chemical_formula_weight         584.68
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-10-30
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.2561(9)
_cell_length_b                   16.0137(5)
_cell_length_c                   8.7122(3)
_cell_measurement_reflns_used    3281
_cell_measurement_temperature    107.0(10)
_cell_measurement_theta_max      70.5050
_cell_measurement_theta_min      4.8200
_cell_volume                     3105.05(19)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      107.0(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9978
_diffrn_measured_fraction_theta_max 0.9790
_diffrn_measurement_details
;
  1 omega   -1.00   30.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -99.0000  -60.0000 31

  2 omega   44.00   75.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -99.0000  -60.0000 31

  3 omega   50.00  112.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -150.0000 62

  4 omega   54.00   91.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 37

  5 omega   51.00   99.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 48

  6 omega   49.00  120.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000 -180.0000 71

  7 omega   40.00   78.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 38

  8 omega   71.00   98.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000    0.0000 27

  9 omega   39.00   84.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 45

 10 omega   18.00   93.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   77.0000  -30.0000 75

 11 omega   57.00  107.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  178.0000 -120.0000 50

 12 omega  -12.00   47.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -77.0000 -120.0000 59

 13 omega  104.00  175.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -90.0000 71

 14 omega  108.00  142.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000    0.0000 34

 15 omega  144.00  172.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  120.0000 28

 16 omega  112.00  141.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  120.0000 29

 17 omega   80.00  107.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  178.0000  150.0000 27

 18 omega   82.00  109.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  178.0000   60.0000 27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0644574000
_diffrn_orient_matrix_UB_12      0.0033022000
_diffrn_orient_matrix_UB_13      -0.0641450000
_diffrn_orient_matrix_UB_21      -0.0096532000
_diffrn_orient_matrix_UB_22      -0.0916538000
_diffrn_orient_matrix_UB_23      0.0474513000
_diffrn_orient_matrix_UB_31      -0.0232246000
_diffrn_orient_matrix_UB_32      0.0289822000
_diffrn_orient_matrix_UB_33      0.1577480000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_av_unetI/netI     0.0570
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            11640
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.119
_diffrn_reflns_theta_min         5.077
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.738
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85465
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_description
;
;
_exptl_crystal_F_000             1256
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.647
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 1952 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     409
_refine_ls_number_reflns         5899
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0495
_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^)+(0.0519P)^2^+0.8497P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1192
_refine_ls_wR_factor_ref         0.1257
_reflns_Friedel_coverage         0.755
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.970
_reflns_number_gt                5216
_reflns_number_total             5899
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00281_si_002.cif
_cod_data_source_block           exp_5646
_cod_database_code               1552667
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.687
_shelx_hkl_checksum              48237
_shelx_res_checksum              75599
_shelx_shelxl_version_number     2014/7