Biological and chemical guided isolation of 3,4-secograyanane diterpenoids from the roots of Pieris formosa
Niu, Chang-Shan; Li, Yong; Liu, Yun-Bao; Ma, Shuang-Gang; Liu, Fei; Li, Li; Xu, Song; Wang, Xiao-Jing; Liu, Sheng; Wang, Ru-Bing; Qu, Jing; Yu, Shi-Shan; RSC Adv. 7 (2017) 43921–; doi:10.1039/C7RA08635K

data_7229150
_publ_section_title
;
 Biological and chemical guided isolation of 3,4-secograyanane
 diterpenoids from the roots of Pieris formosa
;
_journal_issue                   69
_journal_name_full               'RSC Adv.'
_journal_page_first              43921
_journal_paper_doi               10.1039/C7RA08635K
_journal_volume                  7
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C33 H44 O15, O'
_chemical_formula_sum            'C33 H44 O16'
_chemical_formula_weight         696.68
_chemical_name_systematic        'secopierisformoside A'
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-01-05
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_audit_update_record
;
2017-05-07 deposited with the CCDC.
2017-08-23 downloaded from the CCDC.
;
_cell_angle_alpha                64.176(4)
_cell_angle_beta                 89.183(3)
_cell_angle_gamma                76.713(4)
_cell_formula_units_Z            3
_cell_length_a                   8.6705(4)
_cell_length_b                   18.6150(9)
_cell_length_c                   18.7494(7)
_cell_measurement_reflns_used    17831
_cell_measurement_temperature    104.3
_cell_measurement_theta_max      71.0916
_cell_measurement_theta_min      4.5487
_cell_volume                     2638.3(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'A short history of SHELX (Sheldrick, 2007)'
_diffrn_ambient_temperature      104.3
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details
;
  1 omega  -53.00  -22.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  123.0000 -174.0000 31

  2 omega  -51.00  -16.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  149.0000   58.0000 35

  3 omega  -24.00   64.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -80.0000  176.0000 88

  4 omega  -21.00   53.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -37.0000 -150.0000 74

  5 omega   39.00   65.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   37.0000  -90.0000 26

  6 omega  -32.00   42.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -37.0000   60.0000 74

  7 omega   11.00  104.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   77.0000  -60.0000 93

  8 omega   33.00  104.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   37.0000   60.0000 71

  9 omega   51.00   97.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919 -148.0000  121.0000 46

 10 omega  -19.00   66.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   37.0000   30.0000 85

 11 omega  -68.00  -24.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -77.0000 -120.0000 44

 12 omega  -21.00   19.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -77.0000 -120.0000 40

 13 omega  -21.00   57.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       39.7922  -37.0000  -30.0000 78

 14 omega   13.00  102.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       39.7922   77.0000 -150.0000 89

 15 omega   10.00   47.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       39.7922   82.0000  -62.0000 37

 16 omega   52.00  108.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       39.7922   37.0000  -30.0000 56

 17 omega   22.00   56.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       39.7922  -37.0000 -120.0000 34

 18 omega   13.00  103.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       39.7922   77.0000   90.0000 90

 19 omega   13.00  100.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       39.7922   77.0000  150.0000 87

 20 omega   13.00   57.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       39.7922   77.0000   30.0000 44

 21 omega   80.00  106.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       39.7922   77.0000   30.0000 26

 22 omega   66.00  105.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       39.7922 -149.0000   11.0000 39

 23 omega   11.00   38.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       44.0000   89.0000   55.0000 27

 24 omega   18.00   43.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       48.0000   82.0000  -69.0000 25

 25 omega   17.00   42.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       48.0000   84.0000  150.0000 25

 26 omega   24.00   49.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   80.0000    0.0000 25

 27 omega   26.00   70.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   79.0000 -160.0000 44

 28 omega   28.00   72.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   79.0000  108.0000 44

 29 omega   31.00   65.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   74.0000   34.0000 34

 30 omega   99.00  124.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   79.0000  108.0000 25

 31 omega   28.00   89.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   79.0000  -43.0000 61

 32 omega   31.00   56.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   74.0000  -68.0000 25

 33 omega   30.00   81.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   75.0000 -122.0000 51

 34 omega   34.00   59.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   68.0000  104.0000 25

 35 omega   29.00   69.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   78.0000   42.0000 40

 36 omega   28.00   97.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   79.0000  156.0000 69

 37 omega   81.00  149.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   90.0000 68

 38 omega   81.00  172.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 91

 39 omega   41.00  119.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -120.0000   56.0000 78

 40 omega   81.00  171.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 90

 41 omega   81.00  176.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 95

 42 omega   81.00  170.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 89

 43 omega   81.00  163.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -150.0000 82

 44 omega   81.00  176.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  120.0000 95

 45 omega   81.00  176.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 95

 46 omega   41.00  134.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   60.0000 93

 47 omega  131.00  175.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 44

 48 omega   40.00  104.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -123.0000   -5.0000 64

 49 omega   81.00  119.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 38

 50 omega   81.00  150.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  150.0000 69

 51 omega   81.00  106.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 25

 52 omega  136.00  176.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 40

 53 omega   72.00  124.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000   90.0000 52

 54 omega   51.00  122.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -180.0000 71

 55 omega  109.00  134.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -148.0000  -58.0000 25

 56 omega   81.00  175.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 94
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1170743000
_diffrn_orient_matrix_UB_12      0.0777168000
_diffrn_orient_matrix_UB_13      -0.0622788000
_diffrn_orient_matrix_UB_21      -0.1036320000
_diffrn_orient_matrix_UB_22      -0.0538152000
_diffrn_orient_matrix_UB_23      -0.0076124000
_diffrn_orient_matrix_UB_31      -0.0960007000
_diffrn_orient_matrix_UB_32      0.0083848000
_diffrn_orient_matrix_UB_33      0.0669303000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            38245
_diffrn_reflns_theta_full        71.23
_diffrn_reflns_theta_max         71.23
_diffrn_reflns_theta_min         4.55
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.894
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92458
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1110
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.464
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1364
_refine_ls_number_reflns         17761
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0444
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0724P)^2^+0.6266P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1138
_refine_ls_wR_factor_ref         0.1165
_reflns_number_gt                16919
_reflns_number_total             17761
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ra08635k2.cif
_cod_data_source_block           exp_3806
_cod_database_code               7229150
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97