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_1552578
_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 H34 O7'
_chemical_formula_sum            'C29 H34 O7'
_chemical_formula_weight         494.56
_chemical_name_common            'Euphoscopoid D'
_chemical_name_systematic        'Euphoscopoid D'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.9611(3)
_cell_length_b                   12.8686(5)
_cell_length_c                   25.9554(9)
_cell_measurement_reflns_used    7991
_cell_measurement_temperature    178(3)
_cell_measurement_theta_max      62.8960
_cell_measurement_theta_min      3.7950
_cell_volume                     2659.08(17)
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      178(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0288
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
  1 omega   32.00  110.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184 -178.0000 -120.0000 78

  2 omega   13.00  102.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184   57.0000  120.0000 89

  3 omega   13.00  102.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184   57.0000   30.0000 89

  4 omega   18.00   69.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000  150.0000 51

  5 omega   61.00  163.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   30.0000  -90.0000 102

  6 omega   22.00  112.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -61.0000 -150.0000 90

  7 omega   35.00  134.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  178.0000 -120.0000 99

  8 omega   20.00  121.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -77.0000   60.0000 101

  9 omega   20.00  121.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -77.0000    0.0000 101

 10 omega   69.00  159.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   61.0000    0.0000 90

 11 omega   79.00  163.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  111.0000  120.0000 84

 12 omega   19.00   77.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000    0.0000 58

 13 omega   19.00   77.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000  -30.0000 58

 14 omega   18.00   69.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000   90.0000 51

 15 omega   19.00   77.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000   30.0000 58

 16 omega   69.00  159.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   61.0000 -150.0000 90

 17 omega   19.00  129.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -93.0000  -12.9448 110

 18 omega -109.00  -57.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.1184 -178.0000 -150.0000 52

 19 omega   13.00  102.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184   57.0000  -60.0000 89

 20 omega   13.00  102.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184   57.0000 -120.0000 89

 21 omega   67.00  125.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   45.0000   90.0000 58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0046632000
_diffrn_orient_matrix_UB_12      0.0856567000
_diffrn_orient_matrix_UB_13      -0.0414432000
_diffrn_orient_matrix_UB_21      -0.0071233000
_diffrn_orient_matrix_UB_22      -0.0836052000
_diffrn_orient_matrix_UB_23      -0.0424100000
_diffrn_orient_matrix_UB_31      -0.1933371000
_diffrn_orient_matrix_UB_32      0.0008684000
_diffrn_orient_matrix_UB_33      0.0025412000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0990
_diffrn_reflns_av_unetI/netI     0.0752
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            19827
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        62.820
_diffrn_reflns_theta_max         62.820
_diffrn_reflns_theta_min         3.834
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.716
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67104
_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    1.235
_exptl_crystal_description       blocks
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 1272 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(17)
_refine_ls_extinction_coef       0.0020(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     332
_refine_ls_number_reflns         4238
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0434
_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^)+(0.0416P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0864
_refine_ls_wR_factor_ref         0.0924
_reflns_Friedel_coverage         0.735
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                3504
_reflns_number_total             4238
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            1920613.cif
_cod_data_source_block           20160930-ed-bcdb-1
_cod_original_cell_volume        2659.08(18)
_cod_database_code               1552578
_shelx_shelxl_version_number     2016/6
_reflns_odcompleteness_completeness 93.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_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)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1a,H1b), C8(H8a,H8b), C11(H11a,H11b)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), 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)
;
_shelx_res_checksum              76230
_shelx_hkl_checksum              40703
_olex2_submission_special_instructions 'No special instructions were received'