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_1553334
_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 O5'
_chemical_formula_sum            'C13 H13 Cl O5'
_chemical_formula_weight         284.68
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_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                90
_cell_angle_beta                 107.302(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.0660(6)
_cell_length_b                   9.1694(3)
_cell_length_c                   6.5996(2)
_cell_measurement_reflns_used    6397
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.6430
_cell_measurement_theta_min      5.2410
_cell_volume                     1274.89(7)
_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 1.000
_diffrn_measured_fraction_theta_max 0.991
_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  0.0229
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            9242
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.025
_diffrn_reflns_theta_min         4.197
_exptl_absorpt_coefficient_mu    2.804
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.021
_exptl_crystal_size_mid          0.019
_exptl_crystal_size_min          0.018
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.02(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2499
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0336
_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^)+(0.0682P)^2^+0.5673P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.0929
_reflns_Friedel_coverage         0.840
_reflns_Friedel_fraction_full    0.981
_reflns_Friedel_fraction_max     0.951
_reflns_number_gt                2478
_reflns_number_total             2499
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np7b01018_si_005.cif
_cod_data_source_block           aa
_cod_database_code               1553334
_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:
 C2'(H2')
2.b Secondary CH2 refined with riding coordinates:
 C1'(H1'A,H1'B), C3'(H3'A,H3'B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C5(H5), C4(H4)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
2.e Idealised tetrahedral OH refined as rotating group:
 O5(H5A), O3(H3)
;
_olex2_submission_special_instructions 'No special instructions were received'