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_7159142
_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                   7.42770(10)
_cell_length_b                   10.91190(10)
_cell_length_c                   20.6052(2)
_cell_measurement_reflns_used    14372
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.6960
_cell_measurement_theta_min      4.0410
_cell_volume                     1670.06(3)
_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      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_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    -33.00  30.00   0.50    0.50    --    0.00 -82.00  60.00  126
  2  \w     59.00  86.00   0.50    0.50    --    0.00  38.00  60.00   54
  3  \w    -30.00   7.00   0.50    0.50    --    0.00 -82.00 120.00   74
  4  \w      2.00  28.00   0.50    0.50    --    0.00 -82.00-150.00   52
  5  \w    -33.00  28.00   0.50    0.50    --    0.00 -82.00 -60.00  122
  6  \w    -13.00  53.00   0.50    0.50    --    0.00  38.00  60.00  132
  7  \w     81.00 184.00   0.50    0.50    --   95.20  30.00-150.00  206
  8  \w     31.00  91.00   0.50    0.50    --   95.20 -82.00-120.00  120
  9  \w     81.00 156.00   0.50    0.50    --   95.20  30.00 150.00  150
 10  \w     12.00  47.00   0.50    0.50    --   95.20 -45.00 -90.00   70
 11  \w     81.00 115.00   0.50    0.50    --   95.20 -45.00 -90.00   68
 12  \w    114.00 183.00   0.50    0.50    --   95.20  30.00  90.00  138
 13  \w     12.00  38.00   0.50    0.50    --   95.20 -61.00 120.00   52
 14  \w     73.00 173.00   0.50    0.50    --   95.20  61.00   0.00  200
 15  \w     69.00 118.00   0.50    0.50    --   95.20 -82.00 -90.00   98
 16  \w     99.00 185.00   0.50    0.50    --   95.20  77.00 -30.00  172
 17  \w     11.00  80.00   0.50    0.50    --   95.20 -30.00 -60.00  138
 18  \w     82.00 115.00   0.50    0.50    --   95.20  61.00 -30.00   66
 19  \w     45.00  84.00   0.50    0.50    --   95.20 -82.00  60.00   78
 20  \w      6.00  70.00   0.50    0.50    --   95.20 -45.00  30.00  128
 21  \w     67.00 103.00   0.50    0.50    --   95.20 -61.00 120.00   72
 22  \w     96.00 124.00   0.50    0.50    --   95.20  82.00-180.00   56
 23  \w      9.00 107.00   0.50    0.50    --   95.20 -61.00-120.00  196
;
_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      -0.0949825000
_diffrn_orient_matrix_UB_12      -0.1232742000
_diffrn_orient_matrix_UB_13      0.0125770000
_diffrn_orient_matrix_UB_21      -0.0317339000
_diffrn_orient_matrix_UB_22      0.0372776000
_diffrn_orient_matrix_UB_23      0.0711833000
_diffrn_orient_matrix_UB_31      -0.1816021000
_diffrn_orient_matrix_UB_32      0.0580037000
_diffrn_orient_matrix_UB_33      -0.0189945000
_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  0.0246
_diffrn_reflns_av_unetI/netI     0.0141
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            16298
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.911
_diffrn_reflns_theta_min         4.291
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.581
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80225
_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    1.195
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 1364 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.20(7)
_refine_ls_extinction_coef       0.0052(6)
_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   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         3334
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0301
_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^)+(0.0439P)^2^+0.4353P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0824
_refine_ls_wR_factor_ref         0.0826
_reflns_Friedel_coverage         0.711
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.969
_reflns_number_gt                3297
_reflns_number_total             3334
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00005b2.cif
_cod_data_source_block           20220513_syd-18-2
_cod_depositor_comments
'Adding full bibliography for 7159141--7159143.cif.'
_cod_database_code               7159142
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.918
_shelx_estimated_absorpt_t_min   0.823
_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:
 C007(H007)
2.b Secondary CH2 refined with riding coordinates:
 C00B(H00A,H00B), C00D(H00C,H00D), C00G(H00I,H00J), C00H(H00K,H00L), C00K(H00S,
 H00T)
2.c Aromatic/amide H refined with riding coordinates:
 C009(H009), C00E(H00E)
2.d X=CH2 refined with riding coordinates:
 C00M(H00X,H00Y)
2.e Idealised Me refined as rotating group:
 C00F(H00F,H00G,H00H), C00I(H00M,H00N,H00O), C00J(H00P,H00Q,H00R), C00L(H00U,
 H00V,H00W)
2.f Idealised tetrahedral OH refined as rotating group:
 O002(H002)
;
_shelx_res_checksum              68472
_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 2.614
_oxdiff_exptl_absorpt_empirical_full_min 0.397