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_7229152
_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_formula_moiety         'C31 H42 O14, C O, 0.26308(O)'
_chemical_formula_sum            'C32 H42 O15.26'
_chemical_formula_weight         670.84
_chemical_name_systematic        'secopierisformoside N'
_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
_audit_creation_date             2015-11-06
_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
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.7605(3)
_cell_length_b                   15.5108(5)
_cell_length_c                   16.9324(4)
_cell_measurement_reflns_used    5588
_cell_measurement_temperature    102.8
_cell_measurement_theta_max      70.7746
_cell_measurement_theta_min      3.4607
_cell_volume                     3351.35(16)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_diffrn_ambient_temperature      102.8
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
  1 omega  -20.00   11.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -3.5000   57.0000  146.0000 31

  2 omega  -72.00  -22.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -3.5000  -37.0000    0.0000 50

  3 omega   25.00  101.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.8122   37.0000 -180.0000 76

  4 omega   18.00   92.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.8122   37.0000  -90.0000 74

  5 omega   69.00   96.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.8122 -165.0000  -90.0000 27

  6 omega   23.00   87.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.8122   37.0000    0.0000 64

  7 omega   42.00   98.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000    0.0000 56

  8 omega   91.00  176.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   30.0000 85

  9 omega   70.00  146.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000   30.0000 76

 10 omega   45.00   88.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  120.0000 43

 11 omega   43.00   97.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -90.0000 54

 12 omega   73.00   98.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   60.0000 25

 13 omega   42.00   89.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 47

 14 omega   41.00   70.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   60.0000 29

 15 omega   50.00  115.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -116.0000 -145.0000 65
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1095762000
_diffrn_orient_matrix_UB_12      0.0185857000
_diffrn_orient_matrix_UB_13      -0.0342958000
_diffrn_orient_matrix_UB_21      -0.0131251000
_diffrn_orient_matrix_UB_22      0.0963168000
_diffrn_orient_matrix_UB_23      0.0199544000
_diffrn_orient_matrix_UB_31      0.0488702000
_diffrn_orient_matrix_UB_32      -0.0158212000
_diffrn_orient_matrix_UB_33      0.0818634000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12021
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.911
_diffrn_reflns_theta_min         3.865
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.900
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86699
_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    1.330
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.400
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 2505 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     462
_refine_ls_number_reflns         6334
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0366
_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^)+(0.0522P)^2^+0.7858P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0931
_refine_ls_wR_factor_ref         0.0951
_reflns_Friedel_coverage         0.766
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.965
_reflns_number_gt                6045
_reflns_number_total             6334
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ra08635k2.cif
_cod_data_source_block           exp_3590
_cod_database_code               7229152
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_shelx_estimated_absorpt_t_max   0.715
_shelx_estimated_absorpt_t_min   0.687
_shelx_res_checksum              96317
_shelx_shelxl_version_number     2014/7