Peniisocoumarins A-J: Isocoumarins from Penicillium commune QQF-3, an Endophytic Fungus of the Mangrove Plant Kandelia candel.
Cai, Runlin; Wu, Yingnan; Chen, Senhua; Cui, Hui; Liu, Zhaoming; Li, Chunyuan; She, Zhigang; Journal of natural products 81 (2018) 1376–1383; doi:10.1021/acs.jnatprod.7b01018

data_1553335
_publ_section_title
;
 Peniisocoumarins A-J: Isocoumarins from Penicillium commune QQF-3, an
 Endophytic Fungus of the Mangrove Plant Kandelia candel.
;
_journal_issue                   6
_journal_name_full               'Journal of natural products'
_journal_page_first              1376
_journal_page_last               1383
_journal_paper_doi               10.1021/acs.jnatprod.7b01018
_journal_volume                  81
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C13 H13 Cl O6, H2 O'
_chemical_formula_sum            'C13 H15 Cl O7'
_chemical_formula_weight         318.70
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-10-14
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                99.395(7)
_cell_angle_beta                 94.679(8)
_cell_angle_gamma                105.645(7)
_cell_formula_units_Z            1
_cell_length_a                   5.0238(4)
_cell_length_b                   5.5679(4)
_cell_length_c                   12.8812(14)
_cell_measurement_reflns_used    3843
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.6370
_cell_measurement_theta_min      7.0350
_cell_volume                     339.31(5)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0895
_diffrn_reflns_av_unetI/netI     0.0554
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9364
_diffrn_reflns_point_group_measured_fraction_full 0.925
_diffrn_reflns_point_group_measured_fraction_max 0.893
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         75.008
_diffrn_reflns_theta_min         3.509
_exptl_absorpt_coefficient_mu    2.814
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_description       block
_exptl_crystal_F_000             166
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.978
_refine_diff_density_min         -0.748
_refine_diff_density_rms         0.137
_refine_ls_abs_structure_details
;
 Flack x determined using 985 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         2489
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0779
_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^)+(0.1645P)^2^+0.1983P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2170
_refine_ls_wR_factor_ref         0.2196
_reflns_Friedel_coverage         0.825
_reflns_Friedel_fraction_full    0.850
_reflns_Friedel_fraction_max     0.807
_reflns_number_gt                2366
_reflns_number_total             2489
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np7b01018_si_006.cif
_cod_data_source_block           aa
_cod_database_code               1553335
_shelx_shelxl_version_number     2014/7
_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:
 C19(H19)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4)
;
_olex2_submission_special_instructions 'No special instructions were received'