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_1553531
_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_formula_moiety         'C30 H50 O3'
_chemical_formula_sum            'C30 H50 O3'
_chemical_formula_weight         458.70
_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   geom
_audit_creation_date             2016-01-14
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2016-08-07 deposited with the CCDC.
2016-10-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.52391(10)
_cell_length_b                   12.9427(2)
_cell_length_c                   31.7963(6)
_cell_measurement_reflns_used    6184
_cell_measurement_temperature    154.89(10)
_cell_measurement_theta_max      69.7760
_cell_measurement_theta_min      5.3760
_cell_volume                     2684.78(8)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
  1 omega  -21.00   69.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000   60.0000 90

  2 omega  -56.00    0.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  123.0000 -145.0000 56

  3 omega  -15.00   75.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000  150.0000 90

  4 omega   33.00  123.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  -60.0000 90

  5 omega   33.00  123.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000   60.0000 90

  6 omega   33.00  123.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  -90.0000 90

  7 omega   35.00   94.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -120.0000 59

  8 omega  100.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -150.0000 78

  9 omega   36.00  116.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -150.0000 80

 10 omega   35.00   94.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  150.0000 59

 11 omega  100.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000    0.0000 78

 12 omega   36.00   93.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -150.0000 57

 13 omega   57.00  151.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000   90.0000 94

 14 omega   35.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -12.0000  -30.0000 143

 15 omega  -26.00   72.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   38.0000    0.0000 98

 16 omega   28.00  106.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   38.0000 -180.0000 78
;
_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      -0.2333424000
_diffrn_orient_matrix_UB_12      0.0075972000
_diffrn_orient_matrix_UB_13      0.0067520000
_diffrn_orient_matrix_UB_21      0.0266673000
_diffrn_orient_matrix_UB_22      0.1092914000
_diffrn_orient_matrix_UB_23      0.0184002000
_diffrn_orient_matrix_UB_31      -0.0244895000
_diffrn_orient_matrix_UB_32      0.0464831000
_diffrn_orient_matrix_UB_33      -0.0443202000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            14673
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.801
_diffrn_reflns_theta_min         3.687
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.543
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95428
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.135
_exptl_crystal_description       block
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.131
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 1686 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         5019
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0381
_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^)+(0.0566P)^2^+0.1519P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.1006
_reflns_Friedel_coverage         0.727
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                4472
_reflns_number_total             5019
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6qo00460a2.cif
_cod_data_source_block           feidq_1124_2
_cod_original_cell_volume        2684.79(8)
_cod_database_code               1553531
_reflns_odcompleteness_completeness 99.93
_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(H3), C5(H5), C7(H7), C18(H18), C21(H21), C22(H22)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C6(H6A,H6B), C11(H11A,H11B), C12(H12A,H12B),
 C15(H15A,H15B), C16(H16A,H16B), C19(H19A,H19B), C20(H20A,H20B)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), 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.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-11-24
_olex2_submission_special_instructions 'No special instructions were received'