Penitol A and Penicitols E-I: Citrinin Derivatives from <i>Penicillium citrinum</i> and the Structure Revision of Previously Proposed Analogues.
Cheng, Meimei; Li, Pinglin; Jiang, Yun; Tang, Xuli; Zhang, Wenjie; Wang, Qi; Li, Guoqiang; Journal of natural products 84 (2021) 1345–1352; doi:10.1021/acs.jnatprod.1c00082

data_1562350
_publ_section_title
;
 Penitol A and Penicitols E-I: Citrinin Derivatives from <i>Penicillium
 citrinum</i> and the Structure Revision of Previously Proposed Analogues.
;
_journal_issue                   4
_journal_name_full               'Journal of natural products'
_journal_page_first              1345
_journal_page_last               1352
_journal_paper_doi               10.1021/acs.jnatprod.1c00082
_journal_volume                  84
_journal_year                    2021
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C18 H24 O4, C H4 O'
_chemical_formula_sum            'C19 H28 O5'
_chemical_formula_weight         336.41
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-06-16
_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                   8.7654(4)
_cell_length_b                   12.6378(6)
_cell_length_c                   15.3841(7)
_cell_measurement_reflns_used    9889
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      78.39
_cell_measurement_theta_min      2.87
_cell_volume                     1704.18(14)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 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_temperature      150.0
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            38456
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.348
_diffrn_reflns_theta_min         4.528
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.762
_exptl_absorpt_correction_T_max  0.7542
_exptl_absorpt_correction_T_min  0.6694
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1078 before and 0.0549 after correction.
The Ratio of minimum to maximum transmission is 0.8876.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 1464 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         3610
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0302
_refine_ls_R_factor_gt           0.0292
_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^)+(0.0386P)^2^+0.4911P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0756
_refine_ls_wR_factor_ref         0.0765
_reflns_Friedel_coverage         0.736
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.970
_reflns_number_gt                3514
_reflns_number_total             3610
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np1c00082_si_003.cif
_cod_data_source_block           cu_0615_9_0m
_cod_database_code               1562350
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.935
_shelx_estimated_absorpt_t_min   0.921
_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:
 C6(H6), C7(H7), C8(H8), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C15(H15)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C11(H11A,H11B,H11C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3), O5(H5)
;
_shelx_res_checksum              30864
_shelx_hkl_checksum              6861
_olex2_submission_special_instructions 'No special instructions were received'