Macrocyclic Diterpenoids from <i>Euphorbia helioscopia</i> and Their Potential Anti-inflammatory Activity.
Su, Jun-Cheng; Cheng, Wen; Song, Jian-Guo; Zhong, Yuan-Lin; Huang, Xiao-Jun; Jiang, Ren-Wang; Li, Yao-Lan; Li, Man-Mei; Ye, Wen-Cai; Wang, Ying; Journal of natural products 82 (2019) 2818–2827; doi:10.1021/acs.jnatprod.9b00519

data_1552576
_publ_section_title
;
 Macrocyclic Diterpenoids from <i>Euphorbia helioscopia</i> and Their
 Potential Anti-inflammatory Activity.
;
_journal_issue                   10
_journal_name_full               'Journal of natural products'
_journal_page_first              2818
_journal_page_last               2827
_journal_paper_doi               10.1021/acs.jnatprod.9b00519
_journal_volume                  82
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_compound_source        'Euphorbia helioscopia'
_chemical_formula_moiety         'C31 H40 O7'
_chemical_formula_sum            'C31 H40 O7'
_chemical_formula_weight         524.63
_chemical_name_common            'Euphoscopoid E'
_chemical_name_systematic        'Euphoscopoid E'
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-04-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-06-04 deposited with the CCDC.	2019-06-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 89.8590(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.10380(10)
_cell_length_b                   11.62550(10)
_cell_length_c                   13.50580(10)
_cell_measurement_reflns_used    11914
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      73.4780
_cell_measurement_theta_min      3.2300
_cell_volume                     1429.40(2)
_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      120.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_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   -129.00  47.00   1.00    1.00    --  -40.98   0.00-120.00  176
  2  \w     30.00 103.00   1.00    1.00    --   40.98-136.00  29.00   73
  3  \w     25.00 109.00   1.00    1.00    --  106.95 -95.00 120.00   84
  4  \w     25.00 109.00   1.00    1.00    --  106.95 -95.00   0.00   84
  5  \w     79.00 178.00   1.00    1.00    --  106.95  30.00-180.00   99
  6  \w     31.00 135.00   1.00    1.00    --  106.95 -30.00-120.00  104
  7  \w     31.00 135.00   1.00    1.00    --  106.95 -30.00   0.00  104
  8  \w     94.00 178.00   1.00    1.00    --  106.95 125.00 -90.00   84
  9  \w     94.00 178.00   1.00    1.00    --  106.95 125.00 150.00   84
 10  \w   -117.00  -8.00   1.00    1.00    --  -40.98 -77.00 120.00  109
 11  \w   -113.00 -13.00   1.00    1.00    --  -40.98 -57.00-150.00  100
 12  \w     78.00 178.00   1.00    1.00    --  106.95  61.00  30.00  100
 13  \w     78.00 178.00   1.00    1.00    --  106.95  61.00  90.00  100
 14  \w     79.00 178.00   1.00    1.00    --  106.95  30.00 -90.00   99
 15  \w     74.00 178.00   1.00    1.00    --  106.95  77.00 -30.00  104
 16  \w      9.00  89.00   1.00    1.00    --   40.98  74.00  36.00   80
;
_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      -0.0807310000
_diffrn_orient_matrix_UB_12      -0.0668892000
_diffrn_orient_matrix_UB_13      0.0822533000
_diffrn_orient_matrix_UB_21      -0.1487107000
_diffrn_orient_matrix_UB_22      0.0378370000
_diffrn_orient_matrix_UB_23      -0.0433900000
_diffrn_orient_matrix_UB_31      -0.0020253000
_diffrn_orient_matrix_UB_32      -0.1079260000
_diffrn_orient_matrix_UB_33      -0.0660896000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13540
_diffrn_reflns_point_group_measured_fraction_full 0.945
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.656
_diffrn_reflns_theta_min         3.272
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.691
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76095
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_description       block
_exptl_crystal_F_000             564
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 2268 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     350
_refine_ls_number_reflns         5340
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0321
_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^)+(0.0534P)^2^+0.1878P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0831
_refine_ls_wR_factor_ref         0.0833
_reflns_Friedel_coverage         0.775
_reflns_Friedel_fraction_full    0.884
_reflns_Friedel_fraction_max     0.850
_reflns_number_gt                5303
_reflns_number_total             5340
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            1920614.cif
_cod_data_source_block           zq_42
_cod_database_code               1552576
_shelx_shelxl_version_number     2016/6
_reflns_odcompleteness_completeness 99.85
_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
2.a Ternary CH refined with riding coordinates:
 C00B(H00B), C00G(H00G), C00M(H00M), C00N(H00N), C00R(H00R)
2.b Secondary CH2 refined with riding coordinates:
 C00K(H00a,H00e), C00P(H00h,H00i), C00V(H00z,H)
2.c Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00D(H00D), C00F(H00F), C00L(H00L), C00W(H00), C00Y(H1aa),
 C00Z(H2aa), C010(H010)
2.d Idealised Me refined as rotating group:
 C00Q(H00j,H00k,H00o), C00S(H00p,H00q,H00s), C00T(H00t,H00u,H00v), C00U(H00w,
 H00x,H00y), C00X(H0aa,Ha,Hb), C011(H01a,H01b,H01c), C012(H01d,H01e,H01f)
;
_shelx_res_checksum              10849
_shelx_hkl_checksum              25767
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.599
_oxdiff_exptl_absorpt_empirical_full_min 0.638