A novel spirocyclic triterpenoid and a new taraxerane triterpenoid from Teucrium viscidum
Li, Zheng-Yu; Qi, Feng-Ming; Zhi, De-Juan; Hu, Qiao-Ling; Liu, Ying-Hong; Zhang, Zhan-Xin; Fei, Dong-Qing; Organic Chemistry Frontiers 4 (2017) 42–; doi:10.1039/C6QO00460A

data_1553530
_publ_section_title
;
 A novel spirocyclic triterpenoid and a new taraxerane triterpenoid from
 Teucrium viscidum
;
_journal_issue                   1
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              42
_journal_paper_doi               10.1039/C6QO00460A
_journal_volume                  4
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C30 H48 O3, C5 H5 N'
_chemical_formula_sum            'C35 H53 N O3'
_chemical_formula_weight         535.78
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2016-06-22
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-08-07 deposited with the CCDC.
2016-10-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.585(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.4550(5)
_cell_length_b                   11.3624(7)
_cell_length_c                   18.4877(13)
_cell_measurement_reflns_used    4452
_cell_measurement_temperature    273.77(10)
_cell_measurement_theta_max      69.8120
_cell_measurement_theta_min      4.5550
_cell_volume                     1564.44(18)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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_environment      air
_diffrn_ambient_temperature      273.77(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details
;
  1 omega  117.00  177.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 60

  2 omega  124.00  177.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 53

  3 omega  121.00  173.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000  -90.0000 52

  4 omega  111.00  174.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 63

  5 omega   88.00  124.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000   60.0000 36

  6 omega   74.00  114.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000   30.0000 40

  7 omega   82.00  108.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000    0.0000 26

  8 omega   91.00  119.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000    0.0000 28

  9 omega   86.00  121.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000  -60.0000 35

 10 omega   86.00  112.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000  -30.0000 26

 11 omega   87.00  112.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000  -30.0000 25

 12 omega   86.00  120.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000    0.0000 34

 13 omega   87.00  112.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000   30.0000 25

 14 omega   88.00  115.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000   30.0000 27

 15 omega   83.00  108.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000   60.0000 25

 16 omega   83.00  108.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000   30.0000 25

 17 omega   78.00  104.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 26

 18 omega   78.00  104.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 26

 19 omega   78.00  104.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 26

 20 omega   78.00  147.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 69

 21 omega  112.00  140.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   95.0000  131.0000 28

 22 omega   51.00  109.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000    0.0000 58

 23 omega   84.00  177.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 93

 24 omega   92.00  170.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000 -150.0000 78

 25 omega   86.00  161.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000 -180.0000 75

 26 omega   41.00   93.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -90.0000 52

 27 omega   41.00   95.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000  -30.0000 54

 28 omega   50.00   95.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -99.0000   90.0000 45

 29 omega  101.00  126.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   90.0000 25

 30 omega   52.00   97.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   90.0000 45

 31 omega   31.00   78.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000   90.0000 47

 32 omega   28.00   98.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -19.0000   30.0000 70

 33 omega   37.00   64.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000   90.0000 27

 34 omega   33.00   65.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000   30.0000 32

 35 omega   24.00   79.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000   60.0000 55

 36 omega   25.00   50.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000   30.0000 25

 37 omega    1.00   27.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000   30.0000 26

 38 omega  -14.00   11.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000   90.0000 25

 39 omega  -18.00    8.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -19.0000   30.0000 26

 40 omega   -7.00   18.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -38.0000  -60.0000 25

 41 omega  -16.00   84.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -77.0000 -150.0000 100

 42 omega    1.00   45.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -99.0000   90.0000 44

 43 omega  -71.00  -20.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -38.0000  -60.0000 51
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1501848000
_diffrn_orient_matrix_UB_12      -0.0910413000
_diffrn_orient_matrix_UB_13      -0.0148445000
_diffrn_orient_matrix_UB_21      0.0775568000
_diffrn_orient_matrix_UB_22      -0.0286697000
_diffrn_orient_matrix_UB_23      -0.0738163000
_diffrn_orient_matrix_UB_31      0.1191415000
_diffrn_orient_matrix_UB_32      -0.0962051000
_diffrn_orient_matrix_UB_33      0.0360568000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11623
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.800
_diffrn_reflns_theta_min         4.569
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.545
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76709
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
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    1.137
_exptl_crystal_description       block
_exptl_crystal_F_000             588
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 1944 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.12(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         5591
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0567
_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^)+(0.0991P)^2^+0.2248P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1539
_refine_ls_wR_factor_ref         0.1616
_reflns_Friedel_coverage         0.832
_reflns_Friedel_fraction_full    0.935
_reflns_Friedel_fraction_max     0.908
_reflns_number_gt                4965
_reflns_number_total             5591
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6qo00460a2.cif
_cod_data_source_block           feidq_1210
_cod_database_code               1553530
_reflns_odcompleteness_completeness 99.19
_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), C9(H9), C18(H18)
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), C16(H16A,H16B), C19(H19A,H19B), C21(H21A,H21B), C22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C31(H31), C32(H32), C33(H33), C34(H34), C35(H35)
2.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C27(H27A,H27B,
 H27C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'