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_1553383
_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         'C11 H14 O5'
_chemical_formula_sum            'C11 H14 O5'
_chemical_formula_weight         226.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-10-23
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.894(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.2311(6)
_cell_length_b                   13.8888(18)
_cell_length_c                   18.560(2)
_cell_measurement_reflns_used    962
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      74.1780
_cell_measurement_theta_min      4.7740
_cell_volume                     1090.1(2)
_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 21.1652
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.947
_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     24.00 114.00   1.00    1.00    --   43.31  37.00-120.00   90
  2  \w     84.00 169.00   1.00    1.00    --  108.63  77.00 -60.00   85
  3  \w    113.00 144.00   1.00    1.00    --  108.63  15.00  30.00   31
  4  \w     88.00 157.00   1.00    1.00    --  108.63  30.00-120.00   69
  5  \w     39.00 139.00   1.00    1.00    --  108.63 -77.00-180.00  100
  6  \w     40.00  99.00   1.00    1.00    --  108.63-125.00  90.00   59
  7  \w   -110.00 -24.00   1.00    1.00    --  -38.50 -37.00 -30.00   86
;
_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      0.0271285000
_diffrn_orient_matrix_UB_12      0.0358149000
_diffrn_orient_matrix_UB_13      -0.0781144000
_diffrn_orient_matrix_UB_21      -0.1147555000
_diffrn_orient_matrix_UB_22      0.1006422000
_diffrn_orient_matrix_UB_23      0.0228122000
_diffrn_orient_matrix_UB_31      0.3439817000
_diffrn_orient_matrix_UB_32      0.0306024000
_diffrn_orient_matrix_UB_33      0.0165867000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            3531
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.274
_diffrn_reflns_theta_min         3.976
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.924
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70416
_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    1.378
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2144
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.113
_refine_ls_R_factor_all          0.0844
_refine_ls_R_factor_gt           0.0673
_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^)+(0.1192P)^2^+0.4678P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1889
_refine_ls_wR_factor_ref         0.2162
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1653
_reflns_number_total             2144
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np8b00345_si_003.cif
_cod_data_source_block           17090509
_cod_database_code               1553383
_chemical_oxdiff_formula         CHO
_chemical_oxdiff_usercomment     P52-58
_reflns_odcompleteness_completeness 98.97
_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 Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C11(H11A,H11B,H11C)
2.d Idealised tetrahedral OH refined as rotating group:
 O5(H5)
;
_shelx_res_checksum              74627
_shelx_hkl_checksum              55476
_shelx_shelxl_version_number     2014/7
_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 1.899
_oxdiff_exptl_absorpt_empirical_full_min 0.426