Hawaiienols A-D, Highly Oxygenated p-Terphenyls from an Insect-Associated Fungus, Paraconiothyrium hawaiiense.
Ren, Fengxia; Chen, Shenxi; Zhang, Yang; Zhu, Shuaiming; Xiao, Junhai; Liu, Xingzhong; Su, Ruibin; Che, Yongsheng; Journal of natural products 81 (2018) 1752–1759; doi:10.1021/acs.jnatprod.8b00106

data_1553359
_publ_section_title
;
 Hawaiienols A-D, Highly Oxygenated p-Terphenyls from an Insect-Associated
 Fungus, Paraconiothyrium hawaiiense.
;
_journal_issue                   8
_journal_name_full               'Journal of natural products'
_journal_page_first              1752
_journal_page_last               1759
_journal_paper_doi               10.1021/acs.jnatprod.8b00106
_journal_volume                  81
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H20 O7'
_chemical_formula_sum            'C20 H20 O7'
_chemical_formula_weight         372.36
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-06-18
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 110.117(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.3572(3)
_cell_length_b                   11.9056(2)
_cell_length_c                   9.5276(4)
_cell_measurement_reflns_used    4018
_cell_measurement_temperature    97.6
_cell_measurement_theta_max      70.8928
_cell_measurement_theta_min      3.7080
_cell_volume                     890.14(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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-97 (Sheldrick, 1997)'
_computing_structure_solution
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_diffrn_ambient_temperature      97.6
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details
;
  1 omega  -16.00   11.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  111.0000  -30.0000 27

  2 omega   58.00   90.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919 -144.0000  -79.0000 32

  3 omega  -14.00   55.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -37.0000    0.0000 69

  4 omega  -16.00   10.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -77.0000   90.0000 26

  5 omega  -25.00   55.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -37.0000   90.0000 80

  6 omega  -32.00   49.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -37.0000 -180.0000 81

  7 omega   23.00   50.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -77.0000   90.0000 27

  8 omega   31.00   75.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   37.0000  120.0000 44

  9 omega   21.00  105.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   37.0000 -180.0000 84

 10 omega   65.00  101.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919 -144.0000  100.0000 36

 11 omega   41.00   94.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 53

 12 omega  122.00  171.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   90.0000 49

 13 omega   49.00   93.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 44

 14 omega   39.00   65.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -126.0000 -165.0000 26

 15 omega   47.00   83.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 36

 16 omega  126.00  174.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -120.0000 48

 17 omega   44.00  118.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -180.0000 74

 18 omega   53.00   92.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000    0.0000 39

 19 omega   40.00  110.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -126.0000   89.0000 70

 20 omega   55.00  135.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000  -60.0000 80

 21 omega   99.00  135.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -120.0000 36

 22 omega  104.00  176.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -90.0000 72

 23 omega   50.00   94.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   90.0000 44

 24 omega   77.00  122.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -126.0000 -165.0000 45

 25 omega  125.00  174.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  144.0000   79.0000 49

 26 omega   43.00  146.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000  120.0000 103
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0629927000
_diffrn_orient_matrix_UB_12      0.0783359000
_diffrn_orient_matrix_UB_13      -0.0986560000
_diffrn_orient_matrix_UB_21      0.0328826000
_diffrn_orient_matrix_UB_22      -0.1025939000
_diffrn_orient_matrix_UB_23      -0.0847128000
_diffrn_orient_matrix_UB_31      -0.1829442000
_diffrn_orient_matrix_UB_32      0.0084524000
_diffrn_orient_matrix_UB_33      -0.1128801000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0172
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5841
_diffrn_reflns_theta_full        71.05
_diffrn_reflns_theta_max         71.05
_diffrn_reflns_theta_min         5.64
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.885
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3367
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0397
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0754P)^2^+0.2538P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1044
_refine_ls_wR_factor_ref         0.1047
_reflns_number_gt                3344
_reflns_number_total             3367
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            np8b00106_si_002.cif
_cod_data_source_block           exp_2277
_cod_database_code               1553359
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97