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_1552579
_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         'C36 H40 O8, C6 H12'
_chemical_formula_sum            'C42 H52 O8'
_chemical_formula_weight         684.83
_chemical_name_common            'euphorbiapene D'
_chemical_name_systematic        'euphorbiapene D'
_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                 101.170(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.0038(2)
_cell_length_b                   16.8028(3)
_cell_length_c                   11.5827(2)
_cell_measurement_reflns_used    6289
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.5470
_cell_measurement_theta_min      3.8690
_cell_volume                     1910.08(6)
_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 0.999
_diffrn_measured_fraction_theta_max 0.975
_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      5.00  81.00   1.00    1.80    --   41.11 -99.00  90.00   76
  2  \w     54.00  88.00   1.00    1.80    --   41.11-125.00 -30.00   34
  3  \w     45.00 110.00   1.00    8.00    --  107.58 -95.00-150.00   65
  4  \w     94.00 128.00   1.00    8.00    --  107.58 -45.00 -90.00   34
  5  \w     40.00  68.00   1.00    8.00    --  107.58 -45.00 -90.00   28
  6  \w     35.00 133.00   1.00    8.00    --  107.58 -45.00-180.00   98
  7  \w     20.00 157.00   1.00    8.00    --  107.58   0.00 -90.00  137
  8  \w    147.00 172.00   1.00    8.00    --  107.58 125.00  60.00   25
  9  \w    113.00 161.00   1.00    8.00    --  107.58 125.00 -90.00   48
 10  \w      1.00  32.00   1.00    1.80    --   41.11 -99.00 -30.00   31
 11  \w    -81.00 -24.00   1.00    1.80    --  -41.11 -38.00 120.00   57
 12  \w   -115.00 -59.00   1.00    1.80    --  -41.11 -38.00  90.00   56
 13  \w   -103.00 -19.00   1.00    1.80    --  -41.23 -38.00-120.00   84
 14  \w    -36.00  25.00   1.00    1.80    --  -41.23  38.00 -90.00   61
 15  \w    -63.00 -37.00   1.00    1.80    --  -41.23  38.00 -90.00   26
 16  \w     18.00  51.00   1.00    1.80    --   41.23 -38.00-120.00   33
 17  \w    106.00 132.00   1.00    8.00    --  107.58 125.00 120.00   26
 18  \w    101.00 177.00   1.00    8.00    --  107.58  61.00 -30.00   76
 19  \w     80.00 115.00   1.00    8.00    --  107.58-125.00-150.00   35
 20  \w     46.00  72.00   1.00    8.00    --  107.58-125.00-150.00   26
 21  \w    119.00 144.00   1.00   15.00    --  107.58  45.00  60.00   25
;
_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      0.0739645000
_diffrn_orient_matrix_UB_12      0.0372785000
_diffrn_orient_matrix_UB_13      0.1164794000
_diffrn_orient_matrix_UB_21      0.0055012000
_diffrn_orient_matrix_UB_22      0.0805314000
_diffrn_orient_matrix_UB_23      -0.0621659000
_diffrn_orient_matrix_UB_31      -0.1384466000
_diffrn_orient_matrix_UB_32      0.0229994000
_diffrn_orient_matrix_UB_33      0.0302850000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_unetI/netI     0.0576
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11738
_diffrn_reflns_point_group_measured_fraction_full 0.899
_diffrn_reflns_point_group_measured_fraction_max 0.860
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.929
_diffrn_reflns_theta_min         3.890
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.654
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50919
_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    1.191
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.597
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details
;
 Flack x determined using 2261 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     457
_refine_ls_number_reflns         6684
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0623
_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^)+(0.0702P)^2^+2.5827P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1824
_refine_ls_wR_factor_ref         0.1863
_reflns_Friedel_coverage         0.703
_reflns_Friedel_fraction_full    0.791
_reflns_Friedel_fraction_max     0.737
_reflns_number_gt                6114
_reflns_number_total             6684
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            1920617.cif
_cod_data_source_block           zq-39
_cod_database_code               1552579
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.938
_shelx_estimated_absorpt_t_min   0.843
_reflns_odcompleteness_completeness 99.97
_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:
 C2(H2), C3(H3), C4(H4), C7(H7), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1a,H1b), C8(H8a,H8b), C1s(H1sa,H1sb), C2s(H2sa,H2sb), C3s(H3sa,H3sb),
 C4s(H4sa,H4sb), C5s(H5sa,H5sb), C6s(H6sb,H6sa)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C11(H11), C12(H12), C3'(H3'), C4'(H4'), C5'(H5'), C6'(H6'), C7'(H7'),
 C10'(H10'), C11'(H11'), C12'(H12'), C13'(H13'), C14'(H14')
2.d Idealised Me refined as rotating group:
 C16(H16d,H16e,H16f), C17(H17a,H17b,H17c), C18(H18a,H18b,H18c), C19(H19a,H19b,
 H19c), C20(H20a,H20b,H20c), C16'(H16a,H16b,H16c)
;
_shelx_res_checksum              9974
_shelx_hkl_checksum              58134
_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 1.552
_oxdiff_exptl_absorpt_empirical_full_min 0.302