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_1562351
_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         '2(C18 H24 O4), H2 O, C2 H6 O'
_chemical_formula_sum            'C38 H56 O10'
_chemical_formula_weight         672.82
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2020-07-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.172(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.3283(4)
_cell_length_b                   9.4323(4)
_cell_length_c                   17.9581(8)
_cell_measurement_reflns_used    9835
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      78.72
_cell_measurement_theta_min      2.46
_cell_volume                     1749.46(13)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0990
_diffrn_reflns_av_unetI/netI     0.0568
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            42259
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        65.998
_diffrn_reflns_theta_max         65.998
_diffrn_reflns_theta_min         4.925
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.742
_exptl_absorpt_correction_T_max  0.6962
_exptl_absorpt_correction_T_min  0.6046
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1519 before and 0.1082 after correction.
The Ratio of minimum to maximum transmission is 0.8684.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.662
_refine_diff_density_min         -0.783
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
;
 Flack x determined using 2358 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.21(10)
_refine_ls_extinction_coef       0.0077(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     456
_refine_ls_number_reflns         6083
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0548
_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^)+(0.1005P)^2^+0.6959P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1511
_refine_ls_wR_factor_ref         0.1567
_reflns_Friedel_coverage         0.869
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                5504
_reflns_number_total             6083
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np1c00082_si_002.cif
_cod_data_source_block           cu_0703_5_0m
_cod_database_code               1562351
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.923
_shelx_estimated_absorpt_t_min   0.878
_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. Restrained distances
 O1W-H1WA
 0.83 with sigma of 0.02
 C38A-C37A
 1.6 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C37) \\sim Ueq, Uanis(C37A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(O9A) = Uanis(O9)
Uanis(C38A) = Uanis(C38)
Uanis(C37A) = Uanis(C37)
4. Others
 Fixed Sof: O9(0.5) H9(0.5) C38(0.5) H38A(0.5) H38B(0.5) C37(0.5) H37B(0.5)
 H37A(0.5) H37C(0.5) C38A(0.5) H38C(0.5) H38D(0.5) C37A(0.5) H37D(0.5)
 H37E(0.5) H37F(0.5) O9A(0.5) H9A(0.5)
5.a Riding coordinates:
 O1(H1), O1W(H1WA,H1WB)
5.b Ternary CH refined with riding coordinates:
 C6(H6), C7(H7), C14(H14), C15(H15), C24(H24), C25(H25), C32(H32), C33(H33)
5.c Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C20(H20A,H20B), C21(H21A,
 H21B), C22(H22A,H22B), C23(H23A,H23B), C38(H38A,H38B), C38A(H38C,H38D)
5.d Aromatic/amide H refined with riding coordinates:
 C10(H10), C28(H28)
5.e Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C34(H34A,H34B,
 H34C), C35(H35A,H35B,H35C), C36(H36A,H36B,H36C), C37(H37B,H37A,H37C),
 C37A(H37D,H37E,H37F)
5.f Idealised tetrahedral OH refined as rotating group:
 O3(H3), O5(H5), O7(H7A), O9(H9), O9A(H9A)
;
_shelx_res_checksum              18578
_shelx_hkl_checksum              89203
_olex2_submission_special_instructions 'No special instructions were received'