Structurally Diverse Diterpenoids from the Roots of <i>Salvia deserta</i> Based on Nine Different Skeletal Types.
Kadir, Abdukriem; Zheng, Guijuan; Zheng, Xiaofeng; Jin, Pengfei; Maiwulanjiang, Maitinuer; Gao, Biao; Aisa, Haji Akber; Yao, Guangmin; Journal of natural products 84 (2021) 1442–1452; doi:10.1021/acs.jnatprod.0c01180

data_1562540
_publ_section_title
;
 Structurally Diverse Diterpenoids from the Roots of <i>Salvia deserta</i>
 Based on Nine Different Skeletal Types.
;
_journal_issue                   5
_journal_name_full               'Journal of natural products'
_journal_page_first              1442
_journal_page_last               1452
_journal_paper_doi               10.1021/acs.jnatprod.0c01180
_journal_volume                  84
_journal_year                    2021
_chemical_formula_moiety         'C20 H28 O2'
_chemical_formula_sum            'C20 H28 O2'
_chemical_formula_weight         300.42
_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   geom
_audit_creation_date             2020-08-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 108.801(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.1950(11)
_cell_length_b                   8.5829(4)
_cell_length_c                   15.3489(10)
_cell_measurement_reflns_used    9886
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.2240
_cell_measurement_theta_min      3.7240
_cell_volume                     1770.2(2)
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0355
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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     19.00 103.00   1.00    1.00    --   35.24  57.00  90.00   84
  2  \w     18.00  89.00   1.00    1.00    --   35.24-125.00  90.00   71
  3  \w      9.00 103.00   1.00    1.00    --   35.24  77.00 150.00   94
  4  \w    -34.00  54.00   1.00    1.00    --   35.24 -37.00 -30.00   88
  5  \w    -34.00  54.00   1.00    1.00    --   35.24 -37.00-180.00   88
  6  \w     16.00 104.00   1.00    1.00    --   35.24  37.00   0.00   88
  7  \w     18.00  89.00   1.00    1.00    --   35.24-125.00-120.00   71
  8  \w     -4.00  74.00   1.00    1.00    --   35.24 -99.00 -60.00   78
  9  \w     41.00 126.00   1.00    1.00    --  108.00 -61.00 150.00   85
 10  \w     41.00 126.00   1.00    1.00    --  108.00 -61.00-120.00   85
 11  \w     91.00 176.00   1.00    1.00    --  108.00  45.00  30.00   85
 12  \w     57.00 150.00   1.00    1.00    --  108.00 178.00 120.00   93
 13  \w     39.00 177.00   1.00    1.00    --  108.00   0.00   0.00  138
 14  \w     39.00 109.00   1.00    1.00    --  108.00 -94.00  30.00   70
 15  \w     90.00 175.00   1.00    1.00    --  108.00  61.00 -60.00   85
 16  \w     41.00 126.00   1.00    1.00    --  108.00 -61.00  30.00   85
 17  \w     38.00 116.00   1.00    1.00    --  108.00-111.00-180.00   78
 18  \w     37.00 146.00   1.00    1.00    --  108.00 -15.00  90.00  109
 19  \w     38.00 116.00   1.00    1.00    --  108.00-111.00 -60.00   78
 20  \w     39.00 177.00   1.00    1.00    --  108.00   0.00-180.00  138
 21  \w      9.00 103.00   1.00    1.00    --   35.24  77.00-120.00   94
 22  \w    -34.00  54.00   1.00    1.00    --   35.24 -37.00 -90.00   88
 23  \w    -32.00  52.00   1.00    1.00    --   35.24 -57.00  90.00   84
 24  \w     19.00 103.00   1.00    1.00    --   35.24  57.00-120.00   84
 25  \w      9.00 103.00   1.00    1.00    --   35.24  77.00 -60.00   94
 26  \w      9.00 103.00   1.00    1.00    --   35.24  77.00   0.00   94
 27  \w     81.00 176.00   1.00    1.00    --  108.00  77.00-150.00   95
 28  \w     81.00 176.00   1.00    1.00    --  108.00  77.00  90.00   95
 29  \w     10.00  62.00   1.00    1.00    --   35.74  77.00 150.00   52
 30  \w     55.00 105.00   1.00    1.00    --   35.74  37.00  90.00   50
 31  \w      9.00  46.00   1.00    1.00    --   35.74  77.00-180.00   37
 32  \w     12.00  74.00   1.00    1.00    --   35.74  77.00  60.00   62
 33  \w     62.00  90.00   1.00    1.00    --   35.74  77.00 -90.00   28
 34  \w     27.00  54.00   1.00    1.00    --   35.74  77.00 -90.00   27
 35  \w     20.00  68.00   1.00    1.00    --   35.74  57.00 150.00   48
 36  \w     65.00  92.00   1.00    1.00    --   35.74  77.00-180.00   27
 37  \w     19.00  46.00   1.00    1.00    --   35.74  37.00  90.00   27
 38  \w     81.00 106.00   1.00    1.00    --  108.00  77.00-180.00   25
 39  \w     90.00 116.00   1.00    1.00    --  108.00  61.00  60.00   26
 40  \w     81.00 107.00   1.00    1.00    --  108.00  77.00 -60.00   26
 41  \w    149.00 175.00   1.00    1.00    --  108.00  61.00  60.00   26
 42  \w     81.00 106.00   1.00    1.00    --  108.00  77.00  30.00   25
 43  \w    130.00 156.00   1.00    1.00    --  108.00  77.00 -90.00   26
 44  \w     81.00 106.00   1.00    1.00    --  108.00  77.00 150.00   25
 45  \w     81.00 106.00   1.00    1.00    --  108.00  77.00-120.00   25
 46  \w     87.00 113.00   1.00    1.00    --  108.00  30.00-180.00   26
 47  \w     91.00 117.00   1.00    1.00    --  108.00  61.00-150.00   26
 48  \w    137.00 163.00   1.00    1.00    --  108.00  77.00 120.00   26
 49  \w     87.00 113.00   1.00    1.00    --  108.00  30.00-150.00   26
 50  \w     92.00 118.00   1.00    1.00    --  108.00  30.00   0.00   26
 51  \w     81.00 106.00   1.00    1.00    --  108.00  77.00 -90.00   25
 52  \w     87.00 113.00   1.00    1.00    --  108.00  30.00 150.00   26
 53  \w     90.00 116.00   1.00    1.00    --  108.00  61.00  90.00   26
 54  \w     88.00 114.00   1.00    1.00    --  108.00  30.00  30.00   26
 55  \w     87.00 112.00   1.00    1.00    --  108.00  30.00 -60.00   25
 56  \w     81.00 106.00   1.00    1.00    --  108.00  77.00 120.00   25
 57  \w    143.00 169.00   1.00    1.00    --  108.00  30.00 -30.00   26
 58  \w     90.00 116.00   1.00    1.00    --  108.00  61.00 150.00   26
 59  \w     87.00 112.00   1.00    1.00    --  108.00  30.00-120.00   25
 60  \w     89.00 115.00   1.00    1.00    --  108.00  30.00 -30.00   26
 61  \w    141.00 167.00   1.00    1.00    --  108.00  61.00 150.00   26
 62  \w     89.00 118.00   1.00    1.00    --  108.00  30.00  60.00   29
 63  \w     90.00 116.00   1.00    1.00    --  108.00  61.00  30.00   26
 64  \w    147.00 173.00   1.00    1.00    --  108.00  77.00-180.00   26
 65  \w     90.00 116.00   1.00    1.00    --  108.00  61.00 120.00   26
 66  \w     90.00 115.00   1.00    1.00    --  108.00  61.00-180.00   25
 67  \w     81.00 106.00   1.00    1.00    --  108.00  77.00 -30.00   25
 68  \w    135.00 174.00   1.00    1.00    --  108.00  66.00-128.12   39
 69  \w     81.00 106.00   1.00    1.00    --  108.00  77.00   0.00   25
 70  \w     81.00 107.00   1.00    1.00    --  108.00  77.00  60.00   26
 71  \w     92.00 118.00   1.00    1.00    --  108.00  61.00 -90.00   26
 72  \w     90.00 116.00   1.00    1.00    --  108.00  61.00 -30.00   26
 73  \w     71.00  97.00   1.00    1.00    --  108.00  15.00 -60.00   26
 74  \w     87.00 112.00   1.00    1.00    --  108.00  30.00  90.00   25
 75  \w     87.00 112.00   1.00    1.00    --  108.00  66.00-128.12   25
 76  \w   -101.00  -7.00   1.00    1.00    --  -33.50 -77.00 -30.00   94
 77  \w     17.00 105.00   1.00    1.00    --   35.74  37.00-180.00   88
 78  \w     17.00 105.00   1.00    1.00    --   35.74  37.00  90.00   88
 79  \w      9.00 103.00   1.00    1.00    --   35.74  77.00  90.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0696
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            23363
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        66.594
_diffrn_reflns_theta_max         66.594
_diffrn_reflns_theta_min         3.691
_exptl_absorpt_coefficient_mu    0.548
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31312
_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 yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.127
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 1921 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_coef       0.0069(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     410
_refine_ls_number_reflns         6210
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.151
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0595
_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^)+(0.1100P)^2^+0.0991P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1577
_refine_ls_wR_factor_ref         0.1884
_reflns_Friedel_coverage         0.859
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                5297
_reflns_number_total             6210
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np0c01180_si_007.cif
_cod_data_source_block           171201_ygm_ak2_12_7
_cod_depositor_comments
'Adding full bibliography for 1562538--1562543.cif.'
_cod_database_code               1562540
_shelx_shelxl_version_number     2018/3
_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:
 C15(H15), C5'(H5'), C15'(H15'), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C3'(H3'A,H3'B), C1(H1A,H1B), C6'(H6'A,H6'B), C6(H6A,H6B), C2(H2A,H2B),
 C1'(H1'A,H1'B), C3(H3A,H3B), C2'(H2'A,H2'B)
2.c Aromatic/amide H refined with riding coordinates:
 C14'(H14'), C11'(H11'), C11(H11), C14(H14)
2.d Idealised Me refined as rotating group:
 C19'(H19A,H19B,H19C), C17(H17D,H17E,H17F), C20(H20D,H20E,H20F), C20'(H20A,
 H20B,H20C), C16(H16D,H16E,H16F), C18'(H18A,H18B,H18C), C16'(H16A,H16B,H16C),
 C17'(H17A,H17B,H17C), C19(H19D,H19E,H19F), C18(H18D,H18E,H18F)
2.e Idealised tetrahedral OH refined as rotating group:
 O001(H001), O003(H003)
;
_shelx_res_checksum              9007
_shelx_hkl_checksum              80329
_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
;