Heterodimeric Diterpenoids Isolated from Euphorbia ebracteolata Roots and Their Inhibitory Effects on α-Glucosidase.
Wei, Yunlong; Wang, Chao; Cheng, Zhongbin; Tian, Xiangge; Jia, Jingming; Cui, Yonglei; Feng, Lei; Sun, Chengpeng; Zhang, Baojing; Ma, Xiaochi; Journal of natural products 80 (2017) 3218–3223; doi:10.1021/acs.jnatprod.7b00595

data_1548119
_publ_section_title
;
 Heterodimeric Diterpenoids Isolated from Euphorbia ebracteolata Roots and
 Their Inhibitory Effects on \a-Glucosidase.
;
_journal_issue                   12
_journal_name_full               'Journal of natural products'
_journal_page_first              3218
_journal_page_last               3223
_journal_paper_doi               10.1021/acs.jnatprod.7b00595
_journal_volume                  80
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C39 H52 O6, H2 O'
_chemical_formula_sum            'C39 H54 O7'
_chemical_formula_weight         634.82
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'I 2y'
_space_group_name_H-M_alt        'I 1 2 1'
_symmetry_space_group_name_Hall  'I 2y'
_symmetry_space_group_name_H-M   'I 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-04-22
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.6998(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.06063(19)
_cell_length_b                   9.22305(12)
_cell_length_c                   20.6152(2)
_cell_measurement_reflns_used    13789
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.4450
_cell_measurement_theta_min      4.2710
_cell_volume                     3432.45(7)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w   -113.00 -13.00   1.00    1.00    --  -40.98 -57.00  60.00  100
  2  \w   -115.00 -17.00   1.00    1.00    --  -40.98 -37.00-180.00   98
  3  \w    -82.00  39.00   1.00    1.00    --  -40.98  19.00   0.00  121
  4  \w     13.00 113.00   1.00    1.00    --   40.98  57.00  30.00  100
  5  \w     13.00 113.00   1.00    1.00    --   40.98  57.00  90.00  100
  6  \w      8.00 117.00   1.00    1.00    --   40.98  77.00-120.00  109
  7  \w     17.00 115.00   1.00    1.00    --   40.98  37.00   0.00   98
  8  \w     17.00 108.00   1.00    1.00    --   40.98  37.00  60.00   91
  9  \w     36.00  62.00   1.00    1.00    --   40.98  37.00 120.00   26
 10  \w     44.00  97.00   1.00    1.00    --   40.98-125.00 -90.00   53
 11  \w     24.00 103.00   1.00    4.00    --  106.95 -94.00-180.00   79
 12  \w     35.00  93.00   1.00    4.00    --  106.95 -61.00 -60.00   58
 13  \w     74.00 101.00   1.00    4.00    --  106.95  77.00  30.00   27
 14  \w     83.00 110.00   1.00    4.00    --  106.95  45.00  90.00   27
 15  \w     75.00 101.00   1.00    4.00    --  106.95  77.00  60.00   26
 16  \w    113.00 169.00   1.00    4.00    --  106.95  77.00 -30.00   56
 17  \w     78.00 104.00   1.00    4.00    --  106.95  61.00 -60.00   26
 18  \w     78.00 109.00   1.00    4.00    --  106.95  61.00  30.00   31
 19  \w     79.00 106.00   1.00    4.00    --  106.95  61.00   0.00   27
 20  \w     73.00 178.00   1.00    4.00    --  106.95  15.00 120.00  105
 21  \w     94.00 177.00   1.00    4.00    --  106.95 125.00-180.00   83
 22  \w     78.00 112.00   1.00    4.00    --  106.95  61.00  60.00   34
 23  \w     74.00 101.00   1.00    4.00    --  106.95  77.00 -60.00   27
 24  \w    118.00 177.00   1.00    4.00    --  106.95  77.00   0.00   59
 25  \w     81.00 108.00   1.00    4.00    --  106.95  45.00  60.00   27
 26  \w     83.00 108.00   1.00    4.00    --  106.95  30.00 -30.00   25
 27  \w     81.00 143.00   1.00    4.00    --  106.95  45.00 -30.00   62
 28  \w     82.00 107.00   1.00    4.00    --  106.95  45.00  30.00   25
 29  \w     78.00 104.00   1.00    4.00    --  106.95  61.00  90.00   26
 30  \w     81.00 108.00   1.00    4.00    --  106.95  45.00   0.00   27
 31  \w     78.00  90.00   1.00    4.00    --  106.95  61.00 -30.00   12
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0186387000
_diffrn_orient_matrix_UB_12      0.0418070000
_diffrn_orient_matrix_UB_13      0.0709789000
_diffrn_orient_matrix_UB_21      0.0824969000
_diffrn_orient_matrix_UB_22      0.0130426000
_diffrn_orient_matrix_UB_23      -0.0161243000
_diffrn_orient_matrix_UB_31      -0.0115024000
_diffrn_orient_matrix_UB_32      0.1611520000
_diffrn_orient_matrix_UB_33      -0.0170765000
_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     0.0236
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            17055
_diffrn_reflns_point_group_measured_fraction_full 0.924
_diffrn_reflns_point_group_measured_fraction_max 0.890
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.628
_diffrn_reflns_theta_min         4.291
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.661
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77896
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_description       block
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 2478 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     443
_refine_ls_number_reflns         6184
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0288
_refine_ls_R_factor_gt           0.0282
_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^)+(0.0419P)^2^+1.0356P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0730
_refine_ls_wR_factor_ref         0.0735
_reflns_Friedel_coverage         0.711
_reflns_Friedel_fraction_full    0.840
_reflns_Friedel_fraction_max     0.791
_reflns_number_gt                6084
_reflns_number_total             6184
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np7b00595_si_003.cif
_cod_data_source_block           exp_413
_cod_depositor_comments          'Adding full bibliography for 1548119.cif.'
_cod_original_cell_volume        3432.44(7)
_cod_database_code               1548119
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.913
_shelx_estimated_absorpt_t_min   0.874
_reflns_odcompleteness_completeness 99.82
_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:
 C5(H5), C14(H14), C8'(H8'), C9(H9), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C6(H6A,H6B), C3(H3A,H3B), C1(H1A,H1B), C14'(H14A,H14B),
 C11'(H11A,H11B), C2(H2A,H2B), C7'(H7'A,H7'B), C6'(H6'A,H6'B), C12'(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C1'(H1'), C15'(H15')
2.d Idealised Me refined as rotating group:
 C010(H01A,H01B,H01C), C18'(H18A,H18B,H18C), C17(H17A,H17B,H17C), C015(H01D,
 H01E,H01F), C016(H01G,H01H,H01I), C018(H01J,H01K,H01L), C17'(H17D,H17E,H17F)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_res_checksum              18078
_shelx_hkl_checksum              71968
_olex2_date_sample_data_collection 2017-04-22
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.330
_oxdiff_exptl_absorpt_empirical_full_min 0.591