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_1565503
_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         'C24 H30 O6'
_chemical_formula_sum            'C24 H30 O6'
_chemical_formula_weight         414.48
_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
_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                 97.0190(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.96690(10)
_cell_length_b                   8.89930(10)
_cell_length_c                   14.71750(10)
_cell_measurement_reflns_used    9350
_cell_measurement_temperature    106(5)
_cell_measurement_theta_max      74.1290
_cell_measurement_theta_min      5.6090
_cell_volume                     1035.648(19)
_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      106(5)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.983
_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    -25.00   3.00   0.50    0.50    --    0.00 -82.00  90.00   56
  2  \w    -17.00  31.00   0.50    0.50    --    0.00 -82.00 -30.00   96
  3  \w    -17.00  60.00   0.50    0.50    --    0.00  38.00-180.00  154
  4  \w    -30.00   8.00   0.50    0.50    --    0.00 -82.00-150.00   76
  5  \w    -33.00  10.00   0.50    0.50    --    0.00 -82.00  30.00   86
  6  \w     72.00 109.00   0.50    0.50    --   95.80  61.00   0.00   74
  7  \w     36.00 114.00   0.50    0.50    --   95.80 -45.00 -30.00  156
  8  \w     76.00 183.00   0.50    0.50    --   95.80  45.00-180.00  214
  9  \w     81.00 183.00   0.50    0.50    --   95.80  45.00   0.00  204
 10  \w    123.00 184.00   0.50    0.50    --   95.80  61.00 -30.00  122
 11  \w     30.00  56.00   0.50    0.50    --   95.80 -30.00-120.00   52
 12  \w     62.00  99.00   0.50    0.50    --   95.80 -30.00-120.00   74
 13  \w     76.00 182.00   0.50    0.50    --   95.80  45.00  30.00  212
 14  \w     76.00 104.00   0.50    0.50    --   95.80  45.00 -30.00   56
 15  \w     86.00 136.00   0.50    0.50    --   95.80  77.00 120.00  100
 16  \w     76.00 152.00   0.50    0.50    --   95.80  45.00  60.00  152
 17  \w    143.00 174.00   0.50    0.50    --   95.80  77.00 120.00   62
 18  \w     78.00 104.00   0.50    0.50    --   95.80  61.00 -30.00   52
 19  \w     10.00 125.00   0.50    0.50    --   95.80 -77.00 150.00  230
 20  \w     79.00 167.00   0.50    0.50    --   95.80  30.00 -60.00  176
 21  \w     47.00 111.00   0.50    0.50    --   95.80 -15.00-150.00  128
 22  \w     79.00 105.00   0.50    0.50    --   95.80  77.00   0.00   52
 23  \w     80.00 106.00   0.50    0.50    --   95.80  30.00   0.00   52
;
_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      0.0231731000
_diffrn_orient_matrix_UB_12      -0.1089688000
_diffrn_orient_matrix_UB_13      0.0818879000
_diffrn_orient_matrix_UB_21      -0.1932801000
_diffrn_orient_matrix_UB_22      -0.0077902000
_diffrn_orient_matrix_UB_23      -0.0005949000
_diffrn_orient_matrix_UB_31      -0.0075884000
_diffrn_orient_matrix_UB_32      -0.1342952000
_diffrn_orient_matrix_UB_33      -0.0664742000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10892
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.320
_diffrn_reflns_theta_min         3.025
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.773
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93058
_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    1.329
_exptl_crystal_description       needle
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 1800 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4061
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0259
_refine_ls_R_factor_gt           0.0257
_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^)+(0.0377P)^2^+0.1380P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0661
_refine_ls_wR_factor_ref         0.0663
_reflns_Friedel_coverage         0.837
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.940
_reflns_number_gt                4009
_reflns_number_total             4061
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np1c00787_si_005.cif
_cod_data_source_block           wuxiaozhen_pc19-11-8_collect
_cod_database_code               1565503
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C48 H62 N2 O10 '
_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), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C19(H19A,H19B), C9(H9A,H9B), C12(H12A,H12B)
2.c Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C24(H24A,H24B,H24C), C30(H30A,H30B,H30C), C27(H27A,H27B,
 H27C), C22(H22A,H22B,H22C), C25(H25A,H25B,H25C)
2.d Idealised tetrahedral OH refined as rotating group:
 O23(H23)
;
_shelx_res_checksum              15920
_shelx_hkl_checksum              18807
_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 1.118
_oxdiff_exptl_absorpt_empirical_full_min 0.838