Penicisteckins A-F, Isochroman-Derived Atropisomeric Dimers from <i>Penicillium steckii</i> HNNU-5B18.
Wu, Xiao-Zhen; Huang, Wen-Jun; Liu, Wei; Mándi, Attila; Zhang, Qingbo; Zhang, Liping; Zhang, Wenjun; Kurtán, Tibor; Yuan, Cheng-Shan; Zhang, Changsheng; Journal of natural products 84 (2021) 2953–2960; doi:10.1021/acs.jnatprod.1c00787

data_1565502
_publ_section_title
;
 Penicisteckins A-F, Isochroman-Derived Atropisomeric Dimers from
 <i>Penicillium steckii</i> HNNU-5B18.
;
_journal_issue                   11
_journal_name_full               'Journal of natural products'
_journal_page_first              2953
_journal_page_last               2960
_journal_paper_doi               10.1021/acs.jnatprod.1c00787
_journal_volume                  84
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H28 O6'
_chemical_formula_sum            'C23 H28 O6'
_chemical_formula_weight         400.45
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-10-05
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6129(2)
_cell_length_b                   15.0784(5)
_cell_length_c                   17.2106(5)
_cell_measurement_reflns_used    4845
_cell_measurement_temperature    99.9(9)
_cell_measurement_theta_max      72.3560
_cell_measurement_theta_min      3.8750
_cell_volume                     2235.12(11)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(9)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -30.00  31.00   0.50    0.60    --    0.00 -82.00  90.00  122
  2  \w    -20.00  10.00   0.50    0.60    --    0.00 -82.00-120.00   60
  3  \w    -26.00  31.00   0.50    0.60    --    0.00 -82.00-150.00  114
  4  \w      7.00  36.00   0.50    8.00    --   95.80 -30.00 -60.00   58
  5  \w    101.00 173.00   0.50    8.00    --   95.80  82.00 150.00  144
  6  \w     22.00 124.00   0.50    8.00    --   95.80 -77.00-120.00  204
  7  \w    109.00 142.00   0.50    8.00    --   95.80  30.00 -30.00   66
  8  \w     45.00 124.00   0.50    8.00    --   95.80 -77.00  30.00  158
  9  \w    154.00 181.00   0.50    8.00    --   95.80  30.00 -30.00   54
 10  \w     79.00 185.00   0.50    8.00    --   95.80  61.00  60.00  212
 11  \w     88.00 185.00   0.50    8.00    --   95.80  82.00  90.00  194
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1592488000
_diffrn_orient_matrix_UB_12      -0.0238934000
_diffrn_orient_matrix_UB_13      0.0349058000
_diffrn_orient_matrix_UB_21      0.0691772000
_diffrn_orient_matrix_UB_22      -0.0860318000
_diffrn_orient_matrix_UB_23      0.0337633000
_diffrn_orient_matrix_UB_31      0.0431597000
_diffrn_orient_matrix_UB_32      0.0495769000
_diffrn_orient_matrix_UB_33      0.0752123000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10848
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.581
_diffrn_reflns_theta_max         66.581
_diffrn_reflns_theta_min         3.898
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.700
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89405
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 1289 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.12(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3939
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0468
_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^)+(0.0788P)^2^+0.2642P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1271
_refine_ls_wR_factor_ref         0.1311
_reflns_Friedel_coverage         0.745
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3426
_reflns_number_total             3939
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np1c00787_si_003.cif
_cod_data_source_block           wuxiaozhen_pc19-11-6_collect
_cod_database_code               1565502
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C92 H116 N4 O20 '
_shelx_estimated_absorpt_t_max   0.986
_shelx_estimated_absorpt_t_min   0.986
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C1(H1), C19(H19)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C9(H9A,H9B), C18(H18A,H18B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14)
2.d Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C24(H24A,H24B,H24C), C22(H22A,H22B,
 H22C), C26(H26A,H26B,H26C)
2.e Idealised tetrahedral OH refined as rotating group:
 O23(H23)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              74706
_shelx_hkl_checksum              20289
_shelx_fab_checksum              81737
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.099
_oxdiff_exptl_absorpt_empirical_full_min 0.900