Talarolactone A, an Isocoumarin Derivative Fused with Dihydrothiophene with Selective Antimigratory Activity from the Endolichenic Fungus <i>Talaromyces</i> sp.
Yuan, Wei-Hua; Teng, Meng-Ting; Yun, Yang-Fang; Jiang, Nan; Ma, Lin; Sun, Shan-Shan; Yuan, Bo; Tang, Jian; Wu, Qian-Yu; Li, Qian; Zhang, Peng; Morris-Natschke, Susan L; Lee, Kuo-Hsiung; Journal of natural products  (2020) –; doi:10.1021/acs.jnatprod.0c00024

data_1557852
_publ_section_title
;
 Talarolactone A, an Isocoumarin Derivative Fused with Dihydrothiophene
 with Selective Antimigratory Activity from the Endolichenic Fungus
 <i>Talaromyces</i> sp.
;
_journal_name_full               'Journal of natural products'
_journal_paper_doi               10.1021/acs.jnatprod.0c00024
_journal_year                    2020
_chemical_formula_moiety         'C13 H12 O5 S, H2 O'
_chemical_formula_sum            'C13 H14 O6 S'
_chemical_formula_weight         298.30
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2019-04-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.000(6)
_cell_length_b                   9.537(3)
_cell_length_c                   7.754(3)
_cell_measurement_reflns_used    1789
_cell_measurement_temperature    182(2)
_cell_measurement_theta_max      28.027
_cell_measurement_theta_min      2.263
_cell_volume                     1331.1(8)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      181.65
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0542
_diffrn_reflns_av_unetI/netI     0.0737
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6382
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.200
_diffrn_reflns_theta_max         25.200
_diffrn_reflns_theta_min         3.112
_exptl_absorpt_coefficient_mu    0.266
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5791
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 562 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.11(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2373
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0768
_refine_ls_R_factor_gt           0.0559
_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^)+(0.0548P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1146
_refine_ls_wR_factor_ref         0.1239
_reflns_Friedel_coverage         0.828
_reflns_Friedel_fraction_full    0.974
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                1807
_reflns_number_total             2373
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np0c00024_si_002.cif
_cod_data_source_block           a
_cod_database_code               1557852
_shelx_shelxl_version_number     2018/3
_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
2. Restrained distances
 O6-H6A = O6-H6B
 0.85 with sigma of 0.01
 H6A-H6B
 1.45 with sigma of 0.01
 O4-H4A
 0.85 with sigma of 0.01
3.a Ternary CH refined with riding coordinates:
 C9(H9), C8(H8)
3.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
3.c Me refined with riding coordinates:
 C13(H13A,H13B,H13C), C10(H10A,H10B,H10C)
3.d Aromatic/amide H refined with riding coordinates:
 C4(H4)
;
_shelx_res_checksum              56644
_shelx_hkl_checksum              51574
_olex2_submission_special_instructions 'No special instructions were received'