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_1565504
_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         '2(C12 H15 O3)'
_chemical_formula_sum            'C24 H30 O6'
_chemical_formula_weight         414.48
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'I 2y'
_space_group_name_H-M_alt        'I 1 2 1'
_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                 108.589(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.8062(6)
_cell_length_b                   5.45890(10)
_cell_length_c                   21.9181(6)
_cell_measurement_reflns_used    7732
_cell_measurement_temperature    99.9(8)
_cell_measurement_theta_max      73.9240
_cell_measurement_theta_min      3.7590
_cell_volume                     2132.75(10)
_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(8)
_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    -89.00 -52.00   0.50    0.50    --    0.00 -38.00  90.00   74
  2  \w      5.00  31.00   0.50    0.50    --    0.00 -82.00  60.00   52
  3  \w    -26.00  23.00   0.50    0.50    --    0.00 -82.00 150.00   98
  4  \w    -31.00  10.00   0.50    0.50    --    0.00 -38.00  90.00   82
  5  \w    -33.00  30.00   0.50    0.50    --    0.00 -82.00 -30.00  126
  6  \w     42.00  88.00   0.50    0.50    --    0.00  38.00  90.00   92
  7  \w     77.00 104.00   0.50    1.00    --   95.80  45.00-120.00   54
  8  \w      6.00 116.00   0.50    1.00    --   95.80 -61.00   0.00  220
  9  \w    136.00 183.00   0.50    1.00    --   95.80  30.00-150.00   94
 10  \w     79.00 105.00   0.50    1.00    --   95.80  45.00 -90.00   52
 11  \w      6.00  98.00   0.50    1.00    --   95.80 -30.00-180.00  184
 12  \w     74.00  99.00   0.50    1.00    --   95.80  61.00-150.00   50
 13  \w     72.00 185.00   0.50    1.00    --   95.80  15.00 120.00  226
 14  \w     72.00 145.00   0.50    1.00    --   95.80  61.00 -90.00  146
 15  \w     84.00 110.00   0.50    1.00    --   95.80  45.00-150.00   52
 16  \w    136.00 162.00   0.50    1.00    --   95.80  77.00 -60.00   52
 17  \w    155.00 182.00   0.50    1.00    --   95.80  82.00   0.00   54
 18  \w     94.00 148.00   0.50    1.00    --   95.80  82.00   0.00  108
 19  \w     81.00 183.00   0.50    1.00    --   95.80  30.00 150.00  204
 20  \w     72.00  98.00   0.50    1.00    --   95.80  61.00-120.00   52
 21  \w     30.00  55.00   0.50    1.00    --   95.80 -82.00 -30.00   50
 22  \w     79.00 105.00   0.50    1.00    --   95.80 -82.00 -30.00   52
 23  \w     80.00 135.00   0.50    1.00    --   95.80  77.00 -90.00  110
 24  \w     81.00 116.00   0.50    1.00    --   95.80  30.00-120.00   70
 25  \w     83.00 155.00   0.50    1.00    --   95.80  30.00 -90.00  144
 26  \w    131.00 174.00   0.50    1.00    --   95.80  45.00-120.00   86
 27  \w    147.00 184.00   0.50    1.00    --   95.80   0.00  30.00   74
 28  \w     79.00 109.00   0.50    1.00    --   95.80  30.00-150.00   60
 29  \w     56.00 101.00   0.50    1.00    --   95.80 -82.00 150.00   90
;
_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      -0.0683663000
_diffrn_orient_matrix_UB_12      -0.0774411000
_diffrn_orient_matrix_UB_13      -0.0571643000
_diffrn_orient_matrix_UB_21      -0.0299154000
_diffrn_orient_matrix_UB_22      -0.1517553000
_diffrn_orient_matrix_UB_23      0.0458852000
_diffrn_orient_matrix_UB_31      -0.0436284000
_diffrn_orient_matrix_UB_32      0.2248856000
_diffrn_orient_matrix_UB_33      0.0112681000
_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  0.0412
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            10398
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        66.581
_diffrn_reflns_theta_max         66.581
_diffrn_reflns_theta_min         3.747
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.750
_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    1.291
_exptl_crystal_description       needle
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details
;
 Flack x determined using 1532 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         3714
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0493
_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^)+(0.1054P)^2^+0.4601P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1328
_refine_ls_wR_factor_ref         0.1336
_reflns_Friedel_coverage         0.760
_reflns_Friedel_fraction_full    0.958
_reflns_Friedel_fraction_max     0.958
_reflns_number_gt                3622
_reflns_number_total             3714
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np1c00787_si_004.cif
_cod_data_source_block           wuxiaozhen_pc19-11-7_collect
_cod_database_code               1565504
_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:
 C16(H16), C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C5(H5A,H5B), C17(H17A,H17B), C2(H2A,H2B)
2.c Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C14(H14A,H14B,H14C), C11(H11A,H11B,H11C), C30(H30A,H30B,
 H30C), C29(H29A,H29B,H29C), C15(H15A,H15B,H15C)
2.d Idealised tetrahedral OH refined as rotating group:
 O9(H9), O24(H24)
;
_shelx_res_checksum              27596
_shelx_hkl_checksum              59949
_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 1.811
_oxdiff_exptl_absorpt_empirical_full_min 0.542