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_7159141
_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         'C21 H29 N O2, H2 O'
_chemical_formula_sum            'C21 H31 N O3'
_chemical_formula_weight         345.47
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-03-09
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_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                   6.78530(10)
_cell_length_b                   9.85870(10)
_cell_length_c                   28.5856(2)
_cell_measurement_reflns_used    22588
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.6720
_cell_measurement_theta_min      4.7270
_cell_volume                     1912.21(4)
_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 1.3 (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 2018/2 (Sheldrick, 2018)'
_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 0.995
_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    -11.00  77.00   0.50    0.50    --    0.00  38.00   0.00  176
  2  \w    -13.00  17.00   0.50    0.50    --    0.00 -38.00 -90.00   60
  3  \w    -15.00  75.00   0.50    0.50    --    0.00  38.00-120.00  180
  4  \w    -28.00   5.00   0.50    0.50    --    0.00 -82.00-180.00   66
  5  \w    -27.00  28.00   0.50    0.50    --    0.00 -77.00  60.00  110
  6  \w    -14.00  12.00   0.50    0.50    --    0.00  57.00  90.00   52
  7  \w    -14.00  86.00   0.50    0.50    --    0.00  38.00 150.00  200
  8  \w     25.00  68.00   0.50    0.50    --    0.00  57.00  90.00   86
  9  \w    -19.00  28.00   0.50    0.50    --    0.00 -77.00  30.00   94
 10  \w     68.00  98.00   0.50    1.50    --   94.60  69.00 -85.93   60
 11  \w     66.00  92.00   0.50    1.50    --   94.60  74.00 113.61   52
 12  \w     66.00 102.00   0.50    1.50    --   94.60  75.00  61.07   72
 13  \w     96.00 184.00   0.50    1.50    --   94.60  74.00 113.61  176
 14  \w     68.00  94.00   0.50    1.50    --   94.60  70.00-164.98   52
 15  \w     71.00 154.00   0.50    1.50    --   94.60  59.00 109.87  166
 16  \w     73.00 121.00   0.50    1.50    --   94.60  52.00-158.35   96
 17  \w     70.00 179.00   0.50    1.50    --   94.60  64.00-136.02  218
 18  \w     70.00  97.00   0.50    1.50    --   94.60  64.00 162.24   54
 19  \w     67.00 184.00   0.50    1.50    --   94.60  72.00 -48.86  234
 20  \w     67.00  92.00   0.50    1.50    --   94.60  71.00  33.69   50
 21  \w    104.00 129.00   0.50    1.50    --   94.60  64.00 162.24   50
 22  \w     66.00 183.00   0.50    1.50    --   94.60  75.00  45.10  234
 23  \w     71.00 184.00   0.50    1.50    --   94.60  65.00-126.35  226
 24  \w     66.00  91.00   0.50    1.50    --   94.60  74.00 122.32   50
 25  \w     69.00  95.00   0.50    1.50    --   94.60  66.00 -26.49   52
 26  \w    135.00 161.00   0.50    1.50    --   94.60  66.00 -26.49   52
 27  \w     71.00  96.00   0.50    1.50    --   94.60  59.00-137.65   50
 28  \w      5.00  62.00   0.50    1.50    --   94.60 -82.00  30.00  114
 29  \w     80.00 126.00   0.50    1.50    --   94.60 -82.00  30.00   92
 30  \w     67.00  92.00   0.50    1.50    --   94.60  71.00-176.19   50
 31  \w    122.00 173.00   0.50    1.50    --   94.60  67.00 170.43  102
 32  \w     69.00  94.00   0.50    1.50    --   94.60  67.00 170.43   50
 33  \w    159.00 184.00   0.50    1.50    --   94.60  68.00 -19.29   50
 34  \w      6.00 125.00   0.50    1.50    --   94.60 -82.00 150.00  238
 35  \w     67.00  92.00   0.50    1.50    --   94.60  73.00 -65.08   50
 36  \w     71.00  98.00   0.50    1.50    --   94.60  61.00   0.00   54
 37  \w    159.00 184.00   0.50    1.50    --   94.60  61.00   0.00   50
 38  \w     46.00  72.00   0.50    1.50    --   94.60 -82.00-180.00   52
 39  \w     94.00 120.00   0.50    1.50    --   94.60 -82.00-180.00   52
 40  \w     73.00 107.00   0.50    1.50    --   94.60  58.00 -62.37   68
 41  \w    110.00 135.00   0.50    1.50    --   94.60  58.00 -62.37   50
 42  \w    140.00 171.00   0.50    1.50    --   94.60  58.00 -62.37   62
 43  \w     71.00  96.00   0.50    1.50    --   94.60  61.00 -90.00   50
 44  \w    105.00 130.00   0.50    1.50    --   94.60  61.00 -90.00   50
 45  \w     71.00  96.00   0.50    1.50    --   94.60  61.00  90.00   50
 46  \w    108.00 133.00   0.50    1.50    --   94.60  61.00  90.00   50
 47  \w     65.00 126.00   0.50    1.50    --   94.60 -82.00 -60.00  122
 48  \w     89.00 126.00   0.50    1.50    --   94.60 -82.00 -30.00   74
 49  \w     71.00 121.00   0.50    1.50    --   94.60  61.00 150.00  100
 50  \w     17.00  79.00   0.50    1.50    --   94.60 -82.00 -30.00  124
 51  \w    153.00 183.00   0.50    1.50    --   94.60  70.00-164.98   60
 52  \w     69.00 154.00   0.50    1.50    --   94.60  68.00 -19.29  170
 53  \w    156.00 182.00   0.50    1.50    --   94.60  52.00-158.35   52
 54  \w     71.00 181.00   0.50    1.50    --   94.60  61.00  30.00  220
 55  \w     71.00  96.00   0.50    1.50    --   94.60  61.00 120.00   50
 56  \w      7.00  32.00   0.50    1.50    --   94.60 -82.00-120.00   50
 57  \w     48.00  99.00   0.50    1.50    --   94.60 -82.00-120.00  102
 58  \w     71.00  96.00   0.50    1.50    --   94.60  59.00 -96.76   50
 59  \w     75.00 101.00   0.50    1.50    --   94.60  45.00 -90.00   52
 60  \w     69.00 115.00   0.50    1.50    --   94.60  68.00   6.07   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB PRO MM007HF Cu'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0262640000
_diffrn_orient_matrix_UB_12      0.0721878000
_diffrn_orient_matrix_UB_13      0.0473878000
_diffrn_orient_matrix_UB_21      -0.0583199000
_diffrn_orient_matrix_UB_22      -0.1358536000
_diffrn_orient_matrix_UB_23      0.0227666000
_diffrn_orient_matrix_UB_31      0.2178272000
_diffrn_orient_matrix_UB_32      -0.0276442000
_diffrn_orient_matrix_UB_33      0.0118100000
_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  0.0621
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            42221
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.265
_diffrn_reflns_theta_min         3.092
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.626
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60217
_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    1.200
_exptl_crystal_description       needle
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 1534 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         3866
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0317
_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^)+(0.0387P)^2^+0.4589P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0803
_refine_ls_wR_factor_ref         0.0817
_reflns_Friedel_coverage         0.714
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                3760
_reflns_number_total             3866
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00005b2.cif
_cod_data_source_block           20220224_syd-19
_cod_depositor_comments
'Adding full bibliography for 7159141--7159143.cif.'
_cod_database_code               7159141
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.975
_shelx_estimated_absorpt_t_min   0.745
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Rigid bond restraints
 N004, C007
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.005
 N004, C00C
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.005
3.a Free rotating group:
 O002(H00Z,H)
3.b Ternary CH refined with riding coordinates:
 C00C(H00C)
3.c Secondary CH2 refined with riding coordinates:
 C00D(H00A,H00B), C00F(H00D,H00F), C00I(H00G,H00H), C00N(H00T,H00U), C00O(H00V,
 H00W)
3.d Aromatic/amide H refined with riding coordinates:
 N004(H004), C009(H009), C00E(H00E)
3.e Idealised Me refined as rotating group:
 C00J(H00I,H00J,H00K), C00L(H00N,H00O,H00P), C00M(H00Q,H00R,H00S), C00P(H00X,
 H00Y,HA)
3.f Idealised tetrahedral OH refined as rotating group:
 O001(H001)
;
_shelx_res_checksum              1192
_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 2.708
_oxdiff_exptl_absorpt_empirical_full_min 0.385