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_7229151
_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         'C31 H44 O15, H2 O'
_chemical_formula_sum            'C31 H46 O16'
_chemical_formula_weight         674.68
_chemical_name_systematic        'secopierisformoside K'
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-11-25
_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                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.0687(2)
_cell_length_b                   12.2272(4)
_cell_length_c                   23.8020(5)
_cell_measurement_reflns_used    4708
_cell_measurement_temperature    102.3
_cell_measurement_theta_max      71.1969
_cell_measurement_theta_min      3.6130
_cell_volume                     3221.34(14)
_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)/Bruker'
_diffrn_ambient_temperature      102.3
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details
;
  1 omega   37.00   63.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -3.5000   45.0000 -120.0000 26

  2 omega  -13.00   14.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -3.5000   45.0000 -120.0000 27

  3 omega   33.00   62.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -3.5000   77.0000  120.0000 29

  4 omega  -29.00    7.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       34.8240  -77.0000 -120.0000 36

  5 omega   65.00   97.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       34.8240 -148.0000 -165.0000 32

  6 omega   20.00   99.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       34.8240   37.0000 -150.0000 79

  7 omega   18.00  102.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       34.8240   77.0000   90.0000 84

  8 omega   77.00  119.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -123.0000   -1.0000 42

  9 omega   93.00  134.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000   60.0000 41

 10 omega   40.00   98.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  120.0000 58

 11 omega   47.00   95.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 48

 12 omega   91.00  117.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -123.0000  -78.0000 26

 13 omega   43.00  143.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000  150.0000 100

 14 omega   43.00   91.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 48

 15 omega   53.00   87.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000   60.0000 34

 16 omega   63.00  134.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000    0.0000 71
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0110671000
_diffrn_orient_matrix_UB_12      -0.0974791000
_diffrn_orient_matrix_UB_13      0.0406454000
_diffrn_orient_matrix_UB_21      -0.0061428000
_diffrn_orient_matrix_UB_22      0.0789646000
_diffrn_orient_matrix_UB_23      0.0504853000
_diffrn_orient_matrix_UB_31      -0.1385176000
_diffrn_orient_matrix_UB_32      -0.0114564000
_diffrn_orient_matrix_UB_33      0.0010871000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            11345
_diffrn_reflns_theta_full        71.31
_diffrn_reflns_theta_max         71.31
_diffrn_reflns_theta_min         3.71
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.954
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88367
_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    1.391
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     435
_refine_ls_number_reflns         6114
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0480
_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^)+(0.0736P)^2^+0.7173P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1234
_refine_ls_wR_factor_ref         0.1273
_reflns_number_gt                5767
_reflns_number_total             6114
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ra08635k2.cif
_cod_data_source_block           exp_3672
_cod_original_cell_volume        3221.34(15)
_cod_database_code               7229151
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97