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_1565501
_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, C3 H6 O'
_chemical_formula_sum            'C26 H34 O7'
_chemical_formula_weight         458.53
_space_group_crystal_system      trigonal
_space_group_IT_number           144
_space_group_name_Hall           'P 31'
_space_group_name_H-M_alt        'P 31'
_atom_sites_solution_hydrogens   geom
_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                120
_cell_formula_units_Z            3
_cell_length_a                   8.89160(10)
_cell_length_b                   8.89160(10)
_cell_length_c                   25.8071(3)
_cell_measurement_reflns_used    8364
_cell_measurement_temperature    99.9(9)
_cell_measurement_theta_max      73.7330
_cell_measurement_theta_min      5.7560
_cell_volume                     1766.97(3)
_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    -38.00  17.00   0.50    0.50    --    0.00 -57.00 120.00  110
  2  \w    -46.00  28.00   0.50    0.50    --    0.00 -77.00-150.00  148
  3  \w    -71.00 -44.00   0.50    0.50    --    0.00 -57.00 120.00   54
  4  \w    -35.00  -9.00   0.50    0.50    --    0.00 -77.00 -30.00   52
  5  \w     80.00 182.00   0.50    2.00    --   95.80  30.00  90.00  204
  6  \w     13.00  70.00   0.50    2.00    --   95.80 -15.00  60.00  114
  7  \w    117.00 147.00   0.50    2.00    --   95.80  30.00 120.00   60
  8  \w     81.00 115.00   0.50    2.00    --   95.80  30.00 -30.00   68
  9  \w    122.00 184.00   0.50    2.00    --   95.80  45.00-150.00  124
 10  \w    121.00 167.00   0.50    2.00    --   95.80  30.00 -30.00   92
 11  \w     15.00 111.00   0.50    2.00    --   95.80 -30.00 -90.00  192
 12  \w     82.00 183.00   0.50    2.00    --   95.80  30.00 -60.00  202
 13  \w     80.00 185.00   0.50    2.00    --   95.80  30.00  60.00  210
 14  \w     87.00 153.00   0.50    2.00    --   95.80  45.00-120.00  132
;
_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      -0.0060373000
_diffrn_orient_matrix_UB_12      -0.0374048000
_diffrn_orient_matrix_UB_13      0.0584746000
_diffrn_orient_matrix_UB_21      0.0837808000
_diffrn_orient_matrix_UB_22      0.1955752000
_diffrn_orient_matrix_UB_23      0.0114971000
_diffrn_orient_matrix_UB_31      -0.1816227000
_diffrn_orient_matrix_UB_32      -0.0186195000
_diffrn_orient_matrix_UB_33      0.0033717000
_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  0.0323
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            11190
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.598
_diffrn_reflns_theta_max         66.598
_diffrn_reflns_theta_min         5.142
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.762
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.982
_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    1.293
_exptl_crystal_description       block
_exptl_crystal_F_000             738
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.125
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 1939 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         4174
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0293
_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^)+(0.0462P)^2^+0.1453P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0771
_refine_ls_wR_factor_ref         0.0776
_reflns_Friedel_coverage         0.999
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                4040
_reflns_number_total             4174
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np1c00787_si_002.cif
_cod_data_source_block           wuxiaozhen_pc19-11-5_collect
_cod_original_cell_volume        1766.97(4)
_cod_database_code               1565501
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C78 H102 O21 '
_reflns_odcompleteness_completeness 99.95
_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:
 C9(H9A,H9B), C11(H11A,H11B), C2(H2A,H2B), C18(H18A,H18B)
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), C22(H22A,H22B,H22C), C26(H26A,H26B,
 H26C), C32(H32A,H32B,H32C), C24(H24A,H24B,H24C), C33(H33A,H33B,H33C)
2.e Idealised tetrahedral OH refined as rotating group:
 O27(H27), O23(H23)
;
_shelx_res_checksum              869
_shelx_hkl_checksum              75575
_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 1.493
_oxdiff_exptl_absorpt_empirical_full_min 0.736