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_1552580
_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 O8'
_chemical_formula_sum            'C31 H40 O8'
_chemical_formula_weight         540.63
_chemical_name_common            'euphoscopin A'
_chemical_name_systematic        'euphoscopin A'
_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                 92.0110(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.83040(10)
_cell_length_b                   11.79900(10)
_cell_length_c                   13.78790(10)
_cell_measurement_reflns_used    11768
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.3830
_cell_measurement_theta_min      4.9180
_cell_volume                     1435.68(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      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_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   -117.00 -14.00   1.00    1.00    --  -40.46 -37.00  90.00  103
  2  \w   -114.00 -11.00   1.00    1.00    --  -40.46 -57.00-150.00  103
  3  \w   -117.00 -14.00   1.00    1.00    --  -40.46 -37.00-150.00  103
  4  \w    -74.00  38.00   1.00    1.00    --  -40.46  77.00 -30.00  112
  5  \w     23.00  98.00   1.00    1.00    --   40.46-125.00 -90.00   75
  6  \w      1.00  82.00   1.00    1.00    --   40.46 -99.00  90.00   81
  7  \w     11.00 114.00   1.00    1.00    --   40.46  57.00-120.00  103
  8  \w     23.00 109.00   1.00    1.94    --  107.48 -94.00  30.00   86
  9  \w     80.00 178.00   1.00    1.94    --  107.48  45.00-180.00   98
 10  \w     74.00 178.00   1.00    1.94    --  107.48  77.00 -90.00  104
 11  \w     80.00 178.00   1.00    1.94    --  107.48  45.00 150.00   98
 12  \w     74.00 178.00   1.00    1.94    --  107.48  77.00-180.00  104
 13  \w     77.00 178.00   1.00    1.94    --  107.48  61.00 150.00  101
 14  \w     77.00 178.00   1.00    1.94    --  107.48  61.00 120.00  101
 15  \w    100.00 178.00   1.00    1.94    --  107.48 111.00  90.00   78
 16  \w    100.00 178.00   1.00    1.94    --  107.48 111.00 -60.00   78
 17  \w     74.00 178.00   1.00    1.94    --  107.48  77.00 120.00  104
 18  \w     80.00 178.00   1.00    1.94    --  107.48  45.00-120.00   98
 19  \w     74.00 178.00   1.00    1.94    --  107.48  77.00 150.00  104
 20  \w     74.00 171.00   1.00    1.94    --  107.48  77.00  90.00   97
;
_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      0.1040860000
_diffrn_orient_matrix_UB_12      -0.0653890000
_diffrn_orient_matrix_UB_13      0.0724000000
_diffrn_orient_matrix_UB_21      0.1326065000
_diffrn_orient_matrix_UB_22      0.0131254000
_diffrn_orient_matrix_UB_23      -0.0687558000
_diffrn_orient_matrix_UB_31      0.0450522000
_diffrn_orient_matrix_UB_32      0.1123319000
_diffrn_orient_matrix_UB_33      0.0502753000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16386
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.676
_diffrn_reflns_theta_min         4.935
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.731
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81234
_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    1.251
_exptl_crystal_description       blocks
_exptl_crystal_F_000             580
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 2316 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     360
_refine_ls_number_reflns         5464
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0324
_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^)+(0.0515P)^2^+0.1980P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0849
_refine_ls_wR_factor_ref         0.0857
_reflns_Friedel_coverage         0.812
_reflns_Friedel_fraction_full    0.935
_reflns_Friedel_fraction_max     0.891
_reflns_number_gt                5332
_reflns_number_total             5464
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            1920620.cif
_cod_data_source_block           zq-29
_cod_original_cell_volume        1435.67(2)
_cod_database_code               1552580
_shelx_shelxl_version_number     2016/6
_reflns_odcompleteness_completeness 99.96
_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:
 C2(H2), C3(H3a), C4(H4), C7(H7), C13(H13), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1a,H1b), C8(H8a,H8b)
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')
2.d Idealised Me refined as rotating group:
 C16(H16a,H16b,H16c), C17(H17a,H17b,H17c), C18(H18a,H18b,H18c), C19(H19a,H19b,
 H19c), C20(H20a,H20b,H20c), C9'(H9'a,H9'b,H9'c), C11'(H11a,H11b,H11c)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_res_checksum              66912
_shelx_hkl_checksum              63051
_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 1.218
_oxdiff_exptl_absorpt_empirical_full_min 0.771