Highly Oxygenated Triterpenoids and Rare Tetraterpenoids from <i>Abies chensiensis</i> and Their Antibacterial Activity.
Wei, Wen-Jun; Song, Qiu-Yan; Ying, Jin-Chuan; Li, Hang-Ying; Ma, Kai-Liang; Li, Yida; Li, Ya; Gao, Kun; Journal of natural products 82 (2019) 2859–2869; doi:10.1021/acs.jnatprod.9b00616

data_1552571
_publ_section_title
;
 Highly Oxygenated Triterpenoids and Rare Tetraterpenoids from <i>Abies
 chensiensis</i> and Their Antibacterial Activity.
;
_journal_issue                   10
_journal_name_full               'Journal of natural products'
_journal_page_first              2859
_journal_page_last               2869
_journal_paper_doi               10.1021/acs.jnatprod.9b00616
_journal_volume                  82
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C31 H50 O4, C5 H5 N'
_chemical_formula_sum            'C36 H55 N O4'
_chemical_formula_weight         565.81
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2019-02-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                69.350(2)
_cell_angle_beta                 87.717(2)
_cell_angle_gamma                83.935(2)
_cell_formula_units_Z            3
_cell_length_a                   7.3195(2)
_cell_length_b                   16.8609(4)
_cell_length_c                   21.8814(5)
_cell_measurement_reflns_used    19787
_cell_measurement_temperature    292.4(2)
_cell_measurement_theta_max      69.7740
_cell_measurement_theta_min      4.1010
_cell_volume                     2512.80(11)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      292.4(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -69.00  -39.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000 -120.0000 30

  2 omega  -67.00   20.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  -30.0000 87

  3 omega  -27.00   22.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000 -120.0000 49

  4 omega  -79.00  -39.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -77.0000  120.0000 40

  5 omega  -81.00  -35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000   90.0000 46

  6 omega  -32.00   -6.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  130.0000  -11.0000 26

  7 omega  -65.00  -40.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  130.0000  -11.0000 25

  8 omega   -5.00   23.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -77.0000  120.0000 28

  9 omega  -10.00   15.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0000  104.0000   81.1396 25

 10 omega   -1.00   24.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.0000   94.0000  -61.8194 25

 11 omega    9.00   34.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       44.0000   84.0000  150.0731 25

 12 omega    6.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       44.0000   88.0000 -104.9348 27

 13 omega   16.00   45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       48.0000   82.0000  -36.5185 29

 14 omega   13.00   38.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       48.0000   83.0000 -148.9196 25

 15 omega   14.00   39.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       48.0000   82.0000   30.7011 25

 16 omega   15.00   45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       48.0000   80.0000   95.6098 30

 17 omega   18.00   43.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   81.0000   50.5265 25

 18 omega   29.00  112.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000 -180.0000 83

 19 omega   84.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   75.0000  -60.2692 32

 20 omega   76.00  119.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   75.0000 -177.6919 43

 21 omega   25.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   75.0000 -177.6919 38

 22 omega   98.00  125.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   68.0000   91.0077 27

 23 omega   35.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   68.0000   91.0077 31

 24 omega   25.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   75.0000  -60.2692 38

 25 omega   29.00   58.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.0000   75.0000 -120.3520 29

 26 omega   86.00  124.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.0000   73.0000   52.2998 38

 27 omega   31.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.0000   73.0000   52.2998 34

 28 omega   33.00   59.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.0000   69.0000    4.2335 26

 29 omega   38.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   74.0000  122.5518 28

 30 omega  100.00  132.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   74.0000  122.5518 32

 31 omega   46.00   78.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       72.0000   66.0000   16.8396 32

 32 omega  114.00  141.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       72.0000   66.0000   16.8396 27

 33 omega   50.00   76.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       72.0000   57.0000   -0.4776 26

 34 omega  113.00  139.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       72.0000   57.0000   -0.4776 26

 35 omega   45.00  142.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       72.0000   69.0000 -121.3127 97

 36 omega  117.00  145.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       76.0000   66.0000  -37.6117 28

 37 omega   50.00   82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       76.0000   66.0000  -37.6117 32

 38 omega  112.00  147.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       76.0000   77.0000 -162.2208 35

 39 omega   44.00   84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       76.0000   77.0000 -162.2208 40

 40 omega   58.00   84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       80.0000   57.0000  143.7781 26

 41 omega  120.00  146.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       80.0000   70.0000   74.0237 26

 42 omega   53.00   78.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       80.0000   70.0000   74.0237 25

 43 omega  122.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       80.0000   56.0000  164.0049 27

 44 omega   63.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       80.0000   56.0000  164.0049 27

 45 omega   52.00   78.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       80.0000   72.0000   97.7990 26

 46 omega  120.00  150.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       80.0000   72.0000   97.7990 30

 47 omega  119.00  145.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       80.0000   57.0000  143.7781 26

 48 omega   56.00   82.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       84.0000   71.0000   26.3497 26

 49 omega   57.00   82.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       84.0000   70.0000  -78.6148 25

 50 omega  114.00  154.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       84.0000   73.0000  -95.9455 40

 51 omega   55.00   81.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       84.0000   73.0000  -95.9455 26

 52 omega  125.00  154.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       84.0000   70.0000  -78.6148 29

 53 omega  127.00  154.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       84.0000   71.0000   26.3497 27

 54 omega  133.00  158.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       88.0000   69.0000   71.8973 25

 55 omega   61.00   95.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       88.0000   69.0000   71.8973 34

 56 omega  128.00  155.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       88.0000   63.0000   44.8304 27

 57 omega   64.00   90.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       88.0000   63.0000   44.8304 26

 58 omega  129.00  159.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       92.0000   77.0000  165.9855 30

 59 omega   60.00   86.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       92.0000   77.0000  165.9855 26

 60 omega  135.00  162.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       92.0000   72.0000  -16.6362 27

 61 omega   63.00   93.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       92.0000   72.0000  -16.6362 30

 62 omega  141.00  166.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       96.0000   52.0000  127.1871 25

 63 omega   74.00  101.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       96.0000   52.0000  127.1871 27

 64 omega  141.00  166.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       96.0000   74.0000  172.3824 25

 65 omega   66.00   92.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       96.0000   74.0000  172.3824 26

 66 omega  141.00  170.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   69.0000   28.3771 29

 67 omega   76.00  103.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   69.0000   28.3771 27

 68 omega   44.00  114.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -60.0000 70

 69 omega   54.00  109.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  150.0000 55

 70 omega  135.00  174.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -60.0000 39

 71 omega   35.00  146.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -91.0000  -30.0000 111

 72 omega   84.00  147.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000  -30.0000 63

 73 omega   77.00  177.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 100

 74 omega   76.00  153.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  150.0000 77

 75 omega   76.00  176.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 100

 76 omega   76.00  156.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   90.0000 80

 77 omega   47.00  102.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000  -30.0000 55

 78 omega   76.00  171.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -150.0000 95

 79 omega   76.00  177.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 101

 80 omega   76.00  176.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  120.0000 100

 81 omega   76.00  157.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 81

 82 omega   76.00  153.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 77

 83 omega   76.00  150.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 74

 84 omega   76.00  177.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 101

 85 omega   76.00  161.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 85
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1048535000
_diffrn_orient_matrix_UB_12      -0.0306832000
_diffrn_orient_matrix_UB_13      -0.0512924000
_diffrn_orient_matrix_UB_21      0.1023591000
_diffrn_orient_matrix_UB_22      -0.0736509000
_diffrn_orient_matrix_UB_23      0.0550114000
_diffrn_orient_matrix_UB_31      -0.1527371000
_diffrn_orient_matrix_UB_32      -0.0571007000
_diffrn_orient_matrix_UB_33      0.0019428000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            39748
_diffrn_reflns_point_group_measured_fraction_full 0.925
_diffrn_reflns_point_group_measured_fraction_max 0.925
_diffrn_reflns_theta_full        66.595
_diffrn_reflns_theta_max         66.595
_diffrn_reflns_theta_min         4.105
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.557
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48419
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.122
_exptl_crystal_description       block
_exptl_crystal_F_000             930
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.527
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 6703 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1141
_refine_ls_number_reflns         16407
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0432
_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^)+(0.0723P)^2^+0.2973P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1153
_refine_ls_wR_factor_ref         0.1178
_reflns_Friedel_coverage         0.854
_reflns_Friedel_fraction_full    0.852
_reflns_Friedel_fraction_max     0.852
_reflns_number_gt                15637
_reflns_number_total             16407
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00616_si_003.cif
_cod_data_source_block           weiwj_ac_18_1_93
_cod_original_cell_volume        2512.78(12)
_cod_database_code               1552571
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.72
_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:
 C3(H3A), C5(H5), C8(H8), C17(H17), C20(H20), C23(H23), C3A(H3AA), C5A(H5A),
 C8A(H8A), C17A(H17A), C20A(H20A), C23A(H23A), C3B(H3B), C5B(H5B), C8B(H8B),
 C17B(H17B), C20B(H20B), C23B(H23B)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C6(H6A,H6B), C7(H7A,H7B), C11(H11A,H11B), C12(H12A,
 H12B), C15(H15A,H15B), C16(H16A,H16B), C19(H19A,H19B), C22(H22A,H22B),
 C1A(H1AA,H1AB), C2A(H2AA,H2AB), C6A(H6AA,H6AB), C7A(H7AA,H7AB), C11A(H11C,
 H11D), C12A(H12C,H12D), C15A(H15C,H15D), C16A(H16C,H16D), C19A(H19C,H19D),
 C22A(H22C,H22D), C1B(H1BA,H1BB), C2B(H2BA,H2BB), C6B(H6BA,H6BB), C7B(H7BA,
 H7BB), C11B(H11E,H11F), C12B(H12E,H12F), C15B(H15E,H15F), C16B(H16E,H16F),
 C19B(H19E,H19F), C22B(H22E,H22F)
2.c Aromatic/amide H refined with riding coordinates:
 C24(H24), C24A(H24A), C24B(H24B), C32(H32), C33(H33), C34(H34), C35(H35),
 C36(H36), C37(H37), C38(H38), C39(H39), C40(H40), C41(H41), C42(H42), C43(H43),
  C44(H44A), C45(H45), C46(H46)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C21(H21A,H21B,H21C), C27(H27A,H27B,H27C), C28(H28A,H28B,
 H28C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C), C31(H31A,H31B,H31C),
 C18A(H18D,H18E,H18F), C21A(H21D,H21E,H21F), C27A(H27D,H27E,H27F), C28A(H28D,
 H28E,H28F), C29A(H29D,H29E,H29F), C30A(H30D,H30E,H30F), C31A(H31D,H31E,H31F),
 C18B(H18G,H18H,H18I), C21B(H21G,H21H,H21I), C27B(H27G,H27H,H27I), C28B(H28G,
 H28H,H28I), C29B(H29G,H29H,H29I), C30B(H30G,H30H,H30I), C31B(H31G,H31H,H31I)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3), O98(H98), O44(H44), O133(H133)
;
_shelx_res_checksum              72100
_shelx_hkl_checksum              21653
_olex2_date_sample_data_collection 2018-12-03
_olex2_submission_special_instructions 'No special instructions were received'