20-<i>nor</i>-Isopimarane and isopimarane diterpenoids produced by <i>Aspergillus</i> sp. WT03.
Tao, Qiaoqiao; Sang, Yining; Han, Tao; Zhou, Hongling; Zhang, Peng; Cai, Xiaofeng; Organic & biomolecular chemistry 21 (2023) 1895–1902; doi:10.1039/d3ob00005b

data_7159143
_publ_section_title
;
 20-<i>nor</i>-Isopimarane and isopimarane diterpenoids produced by
 <i>Aspergillus</i> sp. WT03.
;
_journal_issue                   9
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1895
_journal_page_last               1902
_journal_paper_doi               10.1039/d3ob00005b
_journal_volume                  21
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H28 O2'
_chemical_formula_sum            'C20 H28 O2'
_chemical_formula_weight         300.42
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-05-13
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-07-23 deposited with the CCDC.	2023-02-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.48213(5)
_cell_length_b                   15.39450(9)
_cell_length_c                   17.15474(11)
_cell_measurement_reflns_used    27208
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.9130
_cell_measurement_theta_min      2.5740
_cell_volume                     1711.86(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_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  28.00   0.50    0.50    --    0.00 -82.00  90.00  106
  2  \w      4.00  34.00   0.50    0.50    --   28.00  72.00  62.56   60
  3  \w     85.00 117.00   0.50    0.50    --   28.00  72.00  62.56   64
  4  \w    -15.00  58.00   0.50    0.50    --   40.00 -41.00-157.07  146
  5  \w    -48.00 -23.00   0.50    0.50    --   40.00 -41.00-157.07   50
  6  \w     23.00  52.00   0.50    0.50    --   48.00  72.00-169.75   58
  7  \w     22.00  91.00   0.50    0.50    --   48.00  70.00 -93.82  138
  8  \w     77.00 132.00   0.50    0.50    --   48.00  72.00-169.75  110
  9  \w    109.00 137.00   0.50    0.50    --   48.00  70.00 -93.82   56
 10  \w     90.00 139.00   0.50    0.50    --   52.00  72.00 118.07   98
 11  \w     26.00  55.00   0.50    0.50    --   52.00  72.00 -53.52   58
 12  \w     25.00  56.00   0.50    0.50    --   52.00  72.00 118.07   62
 13  \w     32.00  60.00   0.50    0.50    --   60.00  75.00  51.82   56
 14  \w     34.00  59.00   0.50    0.50    --   60.00  72.00-136.78   50
 15  \w     39.00  83.00   0.50    0.50    --   64.00  75.00 155.76   88
 16  \w    119.00 145.00   0.50    0.50    --   68.00  75.00-130.84   52
 17  \w     43.00  71.00   0.50    0.50    --   68.00  66.00 141.21   56
 18  \w     40.00  82.00   0.50    0.50    --   68.00  75.00-130.84   84
 19  \w     40.00  66.00   0.50    0.50    --   68.00  74.00  61.83   52
 20  \w     40.00  66.00   0.50    0.50    --   68.00  75.00 -20.08   52
 21  \w     40.00  70.00   0.50    0.50    --   68.00  75.00 -47.67   60
 22  \w    115.00 156.00   0.50    0.50    --   68.00  75.00 -47.67   82
 23  \w     44.00  70.00   0.50    0.50    --   72.00  75.00  79.72   52
 24  \w     44.00  83.00   0.50    0.50    --   72.00  75.00  -6.37   78
 25  \w    139.00 164.00   0.50    0.50    --   76.00  75.00-152.48   50
 26  \w     48.00  73.00   0.50    0.50    --   76.00  75.00-152.48   50
 27  \w     61.00  87.00   0.50    0.50    --   80.00  70.00  68.84   52
 28  \w     54.00  87.00   0.50    0.50    --   80.00  70.00 151.46   66
 29  \w     88.00 185.00   0.50    0.50    --   95.20  45.00 150.00  194
 30  \w     72.00 180.00   0.50    0.50    --   95.20  61.00 -90.00  216
 31  \w     69.00 125.00   0.50    0.50    --   95.20  73.00-144.29  112
 32  \w    107.00 184.00   0.50    0.50    --   95.20  74.00  17.54  154
 33  \w     67.00 101.00   0.50    0.50    --   95.20  74.00  17.54   68
 34  \w     19.00 124.00   0.50    0.50    --   95.20 -77.00  90.00  210
 35  \w     96.00 125.00   0.50    0.50    --   95.20 -77.00 -60.00   58
 36  \w    128.00 162.00   0.50    0.50    --   95.20  61.00-150.00   68
 37  \w     74.00 113.00   0.50    0.50    --   95.20  61.00-150.00   78
 38  \w     20.00  77.00   0.50    0.50    --   95.20 -77.00 -60.00  114
 39  \w     79.00 127.00   0.50    0.50    --   95.20 -82.00 150.00   96
 40  \w     42.00  67.00   0.50    0.50    --   95.20 -82.00 150.00   50
 41  \w    154.00 185.00   0.50    0.50    --   95.20  74.00  93.98   62
 42  \w     72.00 128.00   0.50    0.50    --   95.20  61.00-106.78  112
 43  \w    136.00 184.00   0.50    0.50    --   95.20  61.00-180.00   96
 44  \w     69.00 171.00   0.50    0.50    --   95.20  73.00  37.12  204
 45  \w     72.00  97.00   0.50    0.50    --   95.20  61.00-180.00   50
 46  \w     78.00 177.00   0.50    0.50    --   95.20  55.00 169.63  198
 47  \w     67.00 129.00   0.50    0.50    --   95.20  74.00  93.98  124
 48  \w     44.00 125.00   0.50    0.50    --   95.20 -82.00  60.00  162
 49  \w     74.00 169.00   0.50    0.50    --   95.20  61.00  90.00  190
 50  \w    119.00 159.00   0.50    0.50    --   95.20  74.00 -15.16   80
 51  \w     35.00 126.00   0.50    0.50    --   95.20 -82.00-120.00  182
 52  \w     67.00 116.00   0.50    0.50    --   95.20  74.00 -15.16   98
 53  \w     71.00 183.00   0.50    0.50    --   95.20  64.00 -68.87  224
 54  \w     72.00 184.00   0.50    0.50    --   95.20  61.00 -30.00  224
 55  \w     62.00 124.00   0.50    0.50    --   96.00 -82.00 -30.59  124
;
_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      -0.0457396000
_diffrn_orient_matrix_UB_12      -0.0947120000
_diffrn_orient_matrix_UB_13      -0.0232127000
_diffrn_orient_matrix_UB_21      0.0687750000
_diffrn_orient_matrix_UB_22      -0.0306898000
_diffrn_orient_matrix_UB_23      0.0814277000
_diffrn_orient_matrix_UB_31      -0.2229215000
_diffrn_orient_matrix_UB_32      0.0100095000
_diffrn_orient_matrix_UB_33      0.0298736000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            38508
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.492
_diffrn_reflns_theta_min         3.858
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.566
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56290
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.166
_exptl_crystal_description       needle
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
;
 Flack x determined using 1399 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(7)
_refine_ls_extinction_coef       0.0034(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         3457
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0284
_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^)+(0.0409P)^2^+0.3650P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0762
_refine_ls_wR_factor_ref         0.0767
_reflns_Friedel_coverage         0.719
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                3390
_reflns_number_total             3457
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00005b2.cif
_cod_data_source_block           20220513_syd-18-1
_cod_depositor_comments
'Adding full bibliography for 7159141--7159143.cif.'
_cod_original_cell_volume        1711.857(19)
_cod_database_code               7159143
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.956
_shelx_estimated_absorpt_t_min   0.805
_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:
 C00A(H00A)
2.b Secondary CH2 refined with riding coordinates:
 C00B(H00B,H00C), C00D(H00D,H00E), C00E(H00F,H00G), C00F(H00H,H00I), C00G(H00J,
 H00K)
2.c Aromatic/amide H refined with riding coordinates:
 C004(H004), C00J(H00R)
2.d X=CH2 refined with riding coordinates:
 C00M(H00Y,H)
2.e Idealised Me refined as rotating group:
 C00H(H00L,H00M,H00N), C00I(H00O,H00P,H00Q), C00K(H00S,H00T,H00U), C00L(H00V,
 H00W,H00X)
2.f Idealised tetrahedral OH refined as rotating group:
 O002(H002)
;
_shelx_res_checksum              93453
_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 2.015
_oxdiff_exptl_absorpt_empirical_full_min 0.407