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_1552585
_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         'C29 H36 O7, 0.75(C H4 O)'
_chemical_formula_sum            'C29.75 H38.75 O7.75'
_chemical_formula_weight         521.10
_chemical_name_common            'euphoscopin L'
_chemical_name_systematic        'euphoscopin L'
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-06-04
_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                74.614(4)
_cell_angle_beta                 88.037(3)
_cell_angle_gamma                88.948(3)
_cell_formula_units_Z            2
_cell_length_a                   9.3591(4)
_cell_length_b                   12.5274(5)
_cell_length_c                   12.5470(5)
_cell_measurement_reflns_used    14289
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      62.8890
_cell_measurement_theta_min      5.8970
_cell_volume                     1417.45(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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      173.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0288
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details
;
  1 omega -110.00  -53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -32.9934  178.0000  150.0000 57

  2 omega   13.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       32.9934   57.0000 -150.0000 89

  3 omega   13.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       32.9934   57.0000  -30.0000 89

  4 omega  -11.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       32.9934   19.0000  120.0000 117

  5 omega   35.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       32.9934  178.0000  120.0000 74

  6 omega   35.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       32.9934  178.0000 -120.0000 74

  7 omega   69.00  159.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   61.0000  -60.0000 90

  8 omega   18.00  163.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000    0.0000  120.0000 145

  9 omega   19.00  129.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -93.0000  171.8944 110

 10 omega   35.00  134.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  178.0000 -150.0000 99

 11 omega   19.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000  150.0000 58

 12 omega   18.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000 -111.0000 -180.0000 72

 13 omega   79.00  163.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  111.0000  -30.0000 84

 14 omega   19.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000  -60.0000 58

 15 omega   60.00  161.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000 -180.0000 101

 16 omega   69.00  159.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   61.0000  -30.0000 90

 17 omega   18.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000  -60.0000 51

 18 omega   35.00  134.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  178.0000 -180.0000 99

 19 omega   19.00  128.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -91.0000  -20.2561 109

 20 omega   18.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000 -111.0000  -90.0000 72

 21 omega   20.00  121.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -77.0000  -90.0000 101

 22 omega   22.00  112.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -61.0000 -150.0000 90

 23 omega   19.00   83.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -94.0000    0.0000 64

 24 omega   67.00  162.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   45.0000   60.0000 95

 25 omega   79.00  163.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  111.0000   60.0000 84

 26 omega   69.00  159.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   61.0000  120.0000 90

 27 omega   18.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000 -150.0000 51

 28 omega   19.00   83.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -94.0000  120.0000 64

 29 omega   18.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000 -111.0000 -150.0000 72

 30 omega   19.00  126.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -87.0000   35.5188 107

 31 omega   19.00  129.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -93.0000 -119.3029 110

 32 omega   19.00  129.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -92.0000   72.1188 110

 33 omega -109.00  -57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -32.9934 -178.0000   90.0000 52

 34 omega    3.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       32.9934   77.0000   30.0000 100

 35 omega   13.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       32.9934   57.0000  -90.0000 89

 36 omega    3.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       32.9934   77.0000  -30.0000 100

 37 omega    3.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       32.9934   77.0000  120.0000 100

 38 omega   35.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       32.9934  178.0000 -180.0000 74

 39 omega  -25.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       32.9934  -99.0000    0.0000 100

 40 omega   69.00  129.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   61.0000 -120.0000 60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0448514000
_diffrn_orient_matrix_UB_12      -0.0840819000
_diffrn_orient_matrix_UB_13      0.1074793000
_diffrn_orient_matrix_UB_21      -0.0248052000
_diffrn_orient_matrix_UB_22      0.0885570000
_diffrn_orient_matrix_UB_23      0.0637552000
_diffrn_orient_matrix_UB_31      -0.1565355000
_diffrn_orient_matrix_UB_32      -0.0368485000
_diffrn_orient_matrix_UB_33      0.0247839000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            22578
_diffrn_reflns_point_group_measured_fraction_full 0.828
_diffrn_reflns_point_group_measured_fraction_max 0.828
_diffrn_reflns_theta_full        62.793
_diffrn_reflns_theta_max         62.793
_diffrn_reflns_theta_min         3.655
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.713
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91641
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_description       needles
_exptl_crystal_F_000             558
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.519
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 2912 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   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     702
_refine_ls_number_reflns         7567
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0370
_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^)+(0.0760P)^2^+0.1442P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1046
_refine_ls_wR_factor_ref         0.1053
_reflns_Friedel_coverage         0.674
_reflns_Friedel_fraction_full    0.667
_reflns_Friedel_fraction_max     0.667
_reflns_number_gt                7448
_reflns_number_total             7567
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            1920622.cif
_cod_data_source_block           sujuncheng_ed-ebbdc-2
_cod_depositor_comments
;

2022-11-30
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_weight         1040.71
_cod_original_formula_moiety         '2(C29 H36 O7), C H4 O, 0.5(C H3 O)'
_cod_original_formula_units_Z            1
_cod_original_formula_sum        'C59.50 H77.50 O15.50'
_cod_database_code               1552585
_shelx_shelxl_version_number     2016/6
_reflns_odcompleteness_completeness 96.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     63.60
_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. Others
 Fixed Sof: O2S(0.5) C2S(0.5) H2Sa(0.5) H2Sb(0.5) H2Sc(0.5)
3.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3c), C4(H4), C7(H7), C2a(H2a), C3a(H3aa), C4a(H4a), C7a(H7a)
3.b Secondary CH2 refined with riding coordinates:
 C1(H1a,H1b), C8(H8a,H8b), C11(H11c,H11d), C1a(H1aa,H1ab), C8a(H8aa,H8ab),
 C11a(H11a,H11b)
3.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C12(H12), C3'(H3'), C4'(H4'), C5'(H5'), C6'(H6'), C7'(H7'), C5a(H5a),
 C12a(H12a), C3b(H3b), C4b(H4b), C5b(H5b), C6b(H6b), C7b(H7b)
3.d Idealised Me refined as rotating group:
 C16(H16d,H16e,H16f), C17(H17e,H17d,H17f), C18(H18d,H18e,H18f), C19(H19d,H19e,
 H19f), C20(H20d,H20e,H20f), C9'(H9'a,H9'b,H9'c), C1S(H1Sa,H1Sb,H1Sc), C2S(H2Sa,
 H2Sb,H2Sc), C16a(H16a,H16b,H16c), C17a(H17a,H17b,H17c), C18a(H18a,H18b,H18c),
 C19a(H19a,H19b,H19c), C20a(H20a,H20b,H20c), C9b(H9ba,H9bb,H9bc)
3.e Idealised tetrahedral OH refined as rotating group:
 O3(H3), O1S(H1S), O3a(H3a)
;
_shelx_res_checksum              69161
_shelx_hkl_checksum              25825
_olex2_submission_special_instructions 'No special instructions were received'