Spiro-Phthalides and Isocoumarins Isolated from the Marine-Sponge-Derived Fungus Setosphaeria sp. SCSIO41009.
Pang, Xiaoyan; Lin, Xiuping; Yang, Jie; Zhou, Xuefeng; Yang, Bin; Wang, Junfeng; Liu, Yonghong; Journal of natural products 81 (2018) 1860–1868; doi:10.1021/acs.jnatprod.8b00345

data_1553382
_publ_section_title
;
 Spiro-Phthalides and Isocoumarins Isolated from the Marine-Sponge-Derived
 Fungus Setosphaeria sp. SCSIO41009.
;
_journal_issue                   8
_journal_name_full               'Journal of natural products'
_journal_page_first              1860
_journal_page_last               1868
_journal_paper_doi               10.1021/acs.jnatprod.8b00345
_journal_volume                  81
_journal_year                    2018
_chemical_formula_moiety         'C16 H20 O7'
_chemical_formula_sum            'C16 H20 O7'
_chemical_formula_weight         324.32
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-08-29
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5375)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.73476(8)
_cell_length_b                   8.02415(8)
_cell_length_c                   25.5244(3)
_cell_measurement_reflns_used    5262
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.8080
_cell_measurement_theta_min      5.1190
_cell_volume                     1584.17(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -60.00  31.00   1.00    1.00    --  -42.02  57.00 -30.00   91
  2  \w    -84.00 -18.00   1.00    1.00    --  -42.02 125.00 150.00   66
  3  \w     95.00 176.00   1.00    1.05    --  107.79 125.00 150.00   81
  4  \w     61.00 137.00   1.00    1.05    --  107.79 -61.00 120.00   76
  5  \w     54.00 118.00   1.00    1.05    --  107.79-125.00 150.00   64
  6  \w     35.00 123.00   1.00    1.05    --  107.79 -30.00   0.00   88
  7  \w    -43.00 -18.00   1.00    1.00    --  -41.89 -37.00 -60.00   25
  8  \w   -104.00 -62.00   1.00    1.00    --  -41.89 -37.00 -60.00   42
  9  \w    -93.00 -60.00   1.00    1.00    --  -41.89 -37.00-120.00   33
 10  \w     35.00  61.00   1.00    1.05    --  107.79 -94.00 -30.00   26
 11  \w     84.00 109.00   1.00    1.05    --  107.79 -94.00 -30.00   25
 12  \w    105.00 131.00   1.00    1.05    --  107.79 -61.00  30.00   26
 13  \w    122.00 148.00   1.00    1.05    --  107.79  30.00-120.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1150799000
_diffrn_orient_matrix_UB_12      0.1278234000
_diffrn_orient_matrix_UB_13      -0.0284722000
_diffrn_orient_matrix_UB_21      -0.0015513000
_diffrn_orient_matrix_UB_22      -0.1120108000
_diffrn_orient_matrix_UB_23      -0.0489989000
_diffrn_orient_matrix_UB_31      -0.1625686000
_diffrn_orient_matrix_UB_32      -0.0894068000
_diffrn_orient_matrix_UB_33      0.0207161000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0178
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            6385
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.026
_diffrn_reflns_theta_min         3.463
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.904
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74691
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_description       plate
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 1220 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         3118
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0306
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0486P)^2^+0.1831P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0840
_refine_ls_wR_factor_ref         0.0842
_reflns_Friedel_coverage         0.683
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.945
_reflns_number_gt                3069
_reflns_number_total             3118
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np8b00345_si_001.cif
_cod_data_source_block           17081602
_cod_database_code               1553382
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         CHO
_chemical_oxdiff_usercomment     P52-32
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O7(H7)
;
_olex2_date_sample_data_collection 2017-08-16
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.599
_oxdiff_exptl_absorpt_empirical_full_min 0.590