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_1553381
_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         'C15 H18 O6'
_chemical_formula_sum            'C15 H18 O6'
_chemical_formula_weight         294.29
_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
_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                 95.895(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.6966(3)
_cell_length_b                   5.6223(2)
_cell_length_c                   22.2355(14)
_cell_measurement_reflns_used    3274
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.3450
_cell_measurement_theta_min      5.9290
_cell_volume                     708.39(6)
_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 0.999
_diffrn_measured_fraction_theta_max 0.978
_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     20.00  47.00   1.00    2.50    --   50.00  79.00  66.96   27
  2  \w     33.00  59.00   1.00    2.50    --   62.00  75.00  62.07   26
  3  \w     40.00  77.00   1.00    2.50    --   70.00  77.00  91.14   37
  4  \w     97.00 123.00   1.00    2.50    --   70.00  77.00  91.14   26
  5  \w    108.00 133.00   1.00    2.50    --   62.00  75.00  62.07   25
  6  \w    105.00 131.00   1.00    2.50    --   62.00  76.00  28.66   26
  7  \w    101.00 130.00   1.00    2.50    --   70.00  77.00 -45.86   29
  8  \w    123.00 167.00   1.00    6.00    --  107.38  77.00-120.00   44
  9  \w    115.00 141.00   1.00    6.00    --  107.38  77.00 -60.00   26
 10  \w     88.00 114.00   1.00    2.50    --   66.00  77.00 -13.21   26
 11  \w     77.00 173.00   1.00    6.00    --  107.38  77.00  60.00   96
 12  \w    127.00 157.00   1.00    6.00    --  107.38  77.00  90.00   30
 13  \w     81.00 107.00   1.00    6.00    --  107.38  61.00  90.00   26
 14  \w     81.00 165.00   1.00    6.00    --  107.38  61.00 120.00   84
 15  \w     82.00 172.00   1.00    6.00    --  107.38  61.00 150.00   90
 16  \w     82.00 157.00   1.00    6.00    --  107.38  61.00 -30.00   75
 17  \w     81.00 107.00   1.00    6.00    --  107.38  61.00-120.00   26
 18  \w     81.00 119.00   1.00    6.00    --  107.38  61.00 -90.00   38
 19  \w     82.00 108.00   1.00    6.00    --  107.38  61.00-180.00   26
 20  \w     77.00 103.00   1.00    6.00    --  107.38  77.00-120.00   26
 21  \w     77.00 172.00   1.00    6.00    --  107.38  77.00-150.00   95
 22  \w     81.00 107.00   1.00    6.00    --  107.38  61.00   0.00   26
 23  \w     81.00 107.00   1.00    6.00    --  107.38  61.00  30.00   26
 24  \w     77.00 102.00   1.00    6.00    --  107.38  77.00  90.00   25
 25  \w     77.00 103.00   1.00    6.00    --  107.38  77.00 120.00   26
 26  \w     77.00 102.00   1.00    6.00    --  107.38  77.00 150.00   25
 27  \w     77.00 164.00   1.00    6.00    --  107.38  77.00  30.00   87
 28  \w     77.00 102.00   1.00    6.00    --  107.38  77.00 -30.00   25
 29  \w     77.00 108.00   1.00    6.00    --  107.38  77.00 -60.00   31
 30  \w     77.00 177.00   1.00    6.00    --  107.38  77.00 -90.00  100
 31  \w     77.00 176.00   1.00    6.00    --  107.38  77.00-180.00   99
 32  \w     77.00 178.00   1.00    6.00    --  107.38  77.00   0.00  101
 33  \w     48.00 138.00   1.00    6.00    --  107.38 -77.00   0.00   90
 34  \w     84.00 121.00   1.00    6.00    --  107.38-125.00  30.00   37
 35  \w     39.00 127.00   1.00    6.00    --  107.38 -61.00-120.00   88
 36  \w     36.00  62.00   1.00    2.50    --   66.00  77.00-104.50   26
 37  \w     40.00  83.00   1.00    2.50    --   70.00  77.00-146.42   43
 38  \w     40.00  66.00   1.00    2.50    --   70.00  77.00-179.77   26
 39  \w     40.00  66.00   1.00    2.50    --   70.00  77.00 -90.35   26
 40  \w     40.00  70.00   1.00    2.50    --   70.00  77.00 -45.86   30
 41  \w     36.00  69.00   1.00    2.50    --   66.00  77.00 -13.21   33
 42  \w     32.00  58.00   1.00    2.50    --   62.00  76.00  28.66   26
 43  \w     18.00  43.00   1.00    2.50    --   50.00  82.00 -28.67   25
 44  \w     18.00  43.00   1.00    2.50    --   50.00  82.00-109.21   25
 45  \w      8.00  33.00   1.00    2.50    --   42.00  86.00-145.67   25
 46  \w     -2.00  23.00   1.00    2.50    --   34.00  92.00  37.19   25
 47  \w      7.00  32.00   1.00    2.50    --   42.00  89.00 113.31   25
 48  \w     35.00  62.00   1.00    2.50    --   62.00  75.00 147.56   27
 49  \w     15.00  43.00   1.00    2.50    --   46.00  80.00 170.61   28
 50  \w    -64.00  30.00   1.00    2.50    --  -38.50  57.00  90.00   94
 51  \w     23.00  90.00   1.00    2.50    --   43.56-125.00-150.00   67
 52  \w     28.00 109.00   1.00    6.00    --  107.38 -94.00-150.00   81
 53  \w     39.00 117.00   1.00    6.00    --  107.38-125.00-150.00   78
 54  \w     24.00  95.00   1.00    2.50    --   43.56-125.00   0.00   71
 55  \w   -106.00 -14.00   1.00    2.50    --  -38.50 -57.00 -60.00   92
 56  \w   -110.00 -19.00   1.00    2.50    --  -38.50 -37.00  30.00   91
 57  \w   -115.00 -12.00   1.00    2.50    --  -38.50 -20.00 116.79  103
;
_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      -0.0448247000
_diffrn_orient_matrix_UB_12      0.2667794000
_diffrn_orient_matrix_UB_13      0.0096833000
_diffrn_orient_matrix_UB_21      0.1393094000
_diffrn_orient_matrix_UB_22      -0.0136610000
_diffrn_orient_matrix_UB_23      0.0631012000
_diffrn_orient_matrix_UB_31      0.2291403000
_diffrn_orient_matrix_UB_32      0.0605805000
_diffrn_orient_matrix_UB_33      -0.0279207000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0909
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            12240
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.054
_diffrn_reflns_theta_min         3.997
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.899
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53152
_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    1.380
_exptl_crystal_description       plate
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details
;
 Flack x determined using 933 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2810
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0633
_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^)+(0.1079P)^2^+0.2956P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1729
_refine_ls_wR_factor_ref         0.1907
_reflns_Friedel_coverage         0.789
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.957
_reflns_number_gt                2397
_reflns_number_total             2810
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np8b00345_si_002.cif
_cod_data_source_block           17090410
_cod_original_cell_volume        708.40(7)
_cod_database_code               1553381
_chemical_oxdiff_formula         CHNO
_chemical_oxdiff_usercomment     P52-37
_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:
 C3(H3A)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C11(H11A,H11B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C13(H13A,H13B,H13C)
2.e Idealised tetrahedral OH refined as rotating group:
 O5(H5), O3(H3)
;
_shelx_res_checksum              10631
_shelx_hkl_checksum              58488
_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 2.130
_oxdiff_exptl_absorpt_empirical_full_min 0.486