Versispiroketal A, an unusual tetracyclic bridged spiroketal from the sponge-associated fungus Aspergillus versicolor SCSIO 41013.
Salendra, Limbadri; Luo, Xiaowei; Lin, Xiuping; Wang, Junfeng; Yang, Bin; Zhou, Xuefeng; Liu, Yonghong; Organic & biomolecular chemistry 17 (2019) 2182–2186; doi:10.1039/c9ob00110g

data_7156662
_publ_section_title
;
 Versispiroketal A, an unusual tetracyclic bridged spiroketal from the
 sponge-associated fungus Aspergillus versicolor SCSIO 41013.
;
_journal_issue                   8
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2182
_journal_page_last               2186
_journal_paper_doi               10.1039/c9ob00110g
_journal_volume                  17
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_compound_source        'Marine Fungi'
_chemical_formula_moiety         'C17 H18 O6, H2 O'
_chemical_formula_sum            'C17 H20 O7'
_chemical_formula_weight         336.33
_chemical_name_common            'Versispiroketal A'
_chemical_name_systematic
(1'R,2R,7'S)-4,5',7'-trihydroxy-2',6,7'-trimethylspiro[benzo[d][1,3]dioxole-2,8'-bicyclo[3.2.1]octan]-2'-en-4'-one
_space_group_crystal_system      orthorhombic
_space_group_IT_number           45
_space_group_name_Hall           'I 2 -2c'
_space_group_name_H-M_alt        'I b a 2'
_symmetry_space_group_name_Hall  'I 2 -2c'
_symmetry_space_group_name_H-M   'I b a 2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc20zx97
_audit_creation_date             2018-09-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-11-02 deposited with the CCDC.
2019-01-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   25.1245(4)
_cell_length_b                   17.8586(3)
_cell_length_c                   7.11686(10)
_cell_measurement_reflns_used    4930
_cell_measurement_temperature    100.0(4)
_cell_measurement_theta_max      73.7240
_cell_measurement_theta_min      4.9480
_cell_volume                     3193.25(9)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_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      100.0(4)
_diffrn_detector                 'Pilatus3R 200K-A'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.977
_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    -32.00  24.00   0.50    1.50    --    0.00 -82.00-150.00  112
  2  \w    -20.00   6.00   0.50    1.50    --    0.00 -82.00 120.00   52
  3  \w    -32.00  24.00   0.50    1.50    --    0.00 -82.00 -30.00  112
  4  \w      9.00 114.00   0.50    6.00    --   95.20 -15.00-180.00  210
  5  \w      6.00 123.00   0.50    6.00    --   95.20 -82.00 -30.00  234
  6  \w     93.00 158.00   0.50    6.00    --   95.20  30.00  90.00  130
  7  \w    151.00 184.00   0.50    6.00    --   95.20  82.00 -90.00   66
  8  \w      6.00 115.00   0.50    6.00    --   95.20 -61.00 -30.00  218
  9  \w     13.00  88.00   0.50    6.00    --   95.20 -30.00-180.00  150
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0206579000
_diffrn_orient_matrix_UB_12      0.0803495000
_diffrn_orient_matrix_UB_13      0.0295587000
_diffrn_orient_matrix_UB_21      -0.0433739000
_diffrn_orient_matrix_UB_22      -0.0298326000
_diffrn_orient_matrix_UB_23      0.1332940000
_diffrn_orient_matrix_UB_31      0.0381655000
_diffrn_orient_matrix_UB_32      0.0095382000
_diffrn_orient_matrix_UB_33      0.1678832000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            7658
_diffrn_reflns_point_group_measured_fraction_full 0.854
_diffrn_reflns_point_group_measured_fraction_max 0.815
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.202
_diffrn_reflns_theta_min         3.518
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'MicroMax 007 (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.919
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83299
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_description       needle
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 866 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.15(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         2655
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0345
_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^)+(0.0583P)^2^+1.5799P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0897
_refine_ls_wR_factor_ref         0.0910
_reflns_Friedel_coverage         0.533
_reflns_Friedel_fraction_full    0.679
_reflns_Friedel_fraction_max     0.622
_reflns_number_gt                2542
_reflns_number_total             2655
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob00110g2.cif
_cod_data_source_block           badri_lb25_collect
_cod_depositor_comments          'Adding full bibliography for 7156662.cif.'
_cod_original_cell_volume        3193.26(8)
_cod_database_code               7156662
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C128 H160 N8 O56 '
_shelx_estimated_absorpt_t_max   0.955
_shelx_estimated_absorpt_t_min   0.770
_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, All O(H,H) groups
2.a Free rotating group:
 O24(H24a,H24b)
2.b Ternary CH refined with riding coordinates:
 C4(H4)
2.c Secondary CH2 refined with riding coordinates:
 C7(H7a,H7b)
2.d Aromatic/amide H refined with riding coordinates:
 C16(H16), C6(H6), C14(H14)
2.e Idealised Me refined as rotating group:
 C18(H18a,H18b,H18c), C19(H19a,H19b,H19c), C17(H17a,H17b,H17c)
2.f Idealised tetrahedral OH refined as rotating group:
 O21(H21), O23(H23)
;
_shelx_res_checksum              33298
_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 1.191
_oxdiff_exptl_absorpt_empirical_full_min 0.772