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_1552569
_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_formula_moiety         'C30 H46 O4, C H4 O'
_chemical_formula_sum            'C31 H50 O5'
_chemical_formula_weight         502.71
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2019-03-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.853(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.6034(7)
_cell_length_b                   19.420(2)
_cell_length_c                   11.2933(10)
_cell_measurement_reflns_used    2581
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.2970
_cell_measurement_theta_min      4.5780
_cell_volume                     1440.7(2)
_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      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details
;
  1 omega  -86.00  -52.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000   60.0000 34

  2 omega  -74.00    6.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -63.0000  -60.0000 80

  3 omega  -40.00   -2.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  125.0000 -120.0000 38

  4 omega   71.00  123.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -180.0000 52

  5 omega   22.00   47.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   78.0000   -7.1144 25

  6 omega   39.00   66.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000   30.0000 27

  7 omega   50.00   77.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -150.0000 27

  8 omega  -18.00   78.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -38.0000   30.0000 96

  9 omega   22.00  125.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000   60.0000 103

 10 omega   65.00  151.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000 -150.0000 86

 11 omega   35.00   77.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -91.0000  -60.0000 42

 12 omega  105.00  132.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000   90.0000 27

 13 omega   43.00   86.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000    0.0000 43

 14 omega   38.00  137.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -30.0000 99

 15 omega   68.00  115.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -30.0000 47

 16 omega   42.00   88.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -30.0000 46

 17 omega   37.00   75.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -90.0000 38

 18 omega   40.00   72.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -120.0000 32

 19 omega   72.00  156.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   25.0000  -90.0000 84

 20 omega   34.00   66.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -60.0000 32

 21 omega   85.00  176.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000   60.0000 91

 22 omega   47.00   95.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000 -180.0000 48

 23 omega   38.00   69.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000   90.0000 31

 24 omega   47.00  115.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -180.0000 68
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.2017686000
_diffrn_orient_matrix_UB_12      0.0394305000
_diffrn_orient_matrix_UB_13      -0.0037051000
_diffrn_orient_matrix_UB_21      -0.0870529000
_diffrn_orient_matrix_UB_22      0.0607840000
_diffrn_orient_matrix_UB_23      0.0663259000
_diffrn_orient_matrix_UB_31      0.0817088000
_diffrn_orient_matrix_UB_32      -0.0322921000
_diffrn_orient_matrix_UB_33      0.1200004000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7629
_diffrn_reflns_point_group_measured_fraction_full 0.906
_diffrn_reflns_point_group_measured_fraction_max 0.906
_diffrn_reflns_theta_full        66.597
_diffrn_reflns_theta_max         66.597
_diffrn_reflns_theta_min         3.935
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.602
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90798
_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    1.159
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 1375 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_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     342
_refine_ls_number_reflns         4611
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0932
_refine_ls_R_factor_gt           0.0852
_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^)+(0.1620P)^2^+0.2859P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2403
_refine_ls_wR_factor_ref         0.2512
_reflns_Friedel_coverage         0.805
_reflns_Friedel_fraction_full    0.835
_reflns_Friedel_fraction_max     0.835
_reflns_number_gt                3964
_reflns_number_total             4611
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00616_si_005.cif
_cod_data_source_block           weiwj_ac_19_28
_cod_original_cell_volume        1440.7(3)
_cod_database_code               1552569
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 97.37
_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. Restrained distances
 O1AA-C0AA
 1.4 with sigma of 0.01
3.a Ternary CH refined with riding coordinates:
 C5(H5), C15(H15), C8(H8), C3(H3), C17(H17), C20(H20), C23(H23)
3.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C1(H1A,H1B), C6(H6A,H6B), C11(H11A,H11B), C22(H22A,H22B), C2(H2A,
 H2B), C12(H12A,H12B), C19(H19A,H19B), C16(H16A,H16B)
3.c Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C18(H18A,H18B,H18C), C28(H28A,H28B,H28C), C29(H29A,H29B,
 H29C), C27(H27A,H27B,H27C), C21(H21A,H21B,H21C), C0AA(H0AA,H0AB,H0AC)
3.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O1AA(H1AA)
;
_shelx_res_checksum              70306
_shelx_hkl_checksum              67397
_olex2_date_sample_data_collection 2019-02-28
_olex2_submission_special_instructions 'No special instructions were received'