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_1552584
_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         'C38 H44 O9'
_chemical_formula_sum            'C38 H44 O9'
_chemical_formula_weight         644.73
_chemical_name_common            'euphoscopin C'
_chemical_name_systematic        'euphoscopin C'
_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     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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.83142(10)
_cell_length_b                   18.1776(2)
_cell_length_c                   22.9178(3)
_cell_measurement_reflns_used    12883
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      62.8360
_cell_measurement_theta_min      5.2220
_cell_volume                     3679.09(8)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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_temperature      173.00(10)
_diffrn_detector_area_resol_mean 16.0288
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega   35.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184  178.0000  120.0000 74

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

  3 omega   13.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184   57.0000 -180.0000 89

  4 omega   19.00  129.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -92.0000   -7.7167 110

  5 omega   18.00   69.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000 -180.0000 51

  6 omega   18.00   69.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000  120.0000 51

  7 omega   18.00   69.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000   90.0000 51

  8 omega   18.00   69.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000    0.0000 51

  9 omega   67.00  162.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   45.0000   90.0000 95

 10 omega   19.00   77.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000 -120.0000 58

 11 omega   19.00   77.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000  150.0000 58

 12 omega   22.00  112.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -61.0000   30.0000 90

 13 omega   19.00   77.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000  -30.0000 58

 14 omega   18.00   73.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -24.0000 -112.6035 55

 15 omega   18.00   90.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000 -111.0000   30.0000 72

 16 omega   79.00  163.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  111.0000  -30.0000 84

 17 omega   19.00   83.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -94.0000   60.0000 64

 18 omega   19.00   83.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -94.0000  -90.0000 64

 19 omega   18.00   69.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000 -150.0000 51

 20 omega   19.00  129.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -92.0000  -72.6564 110

 21 omega   19.00  107.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -93.0000   36.3111 88

 22 omega   76.00  107.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -61.0000 -180.0000 31

 23 omega   97.00  144.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   61.0000  -30.0000 47

 24 omega   67.00   93.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -17.0000  -30.7915 26
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0277789000
_diffrn_orient_matrix_UB_12      0.0608893000
_diffrn_orient_matrix_UB_13      0.0455586000
_diffrn_orient_matrix_UB_21      0.0187383000
_diffrn_orient_matrix_UB_22      -0.0589035000
_diffrn_orient_matrix_UB_23      0.0478188000
_diffrn_orient_matrix_UB_31      0.1710804000
_diffrn_orient_matrix_UB_32      -0.0033889000
_diffrn_orient_matrix_UB_33      -0.0125873000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            29939
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        62.747
_diffrn_reflns_theta_max         62.747
_diffrn_reflns_theta_min         5.235
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.672
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70580
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_description       blocks
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.627
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 2387 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     431
_refine_ls_number_reflns         5891
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0447
_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^)+(0.0757P)^2^+0.8488P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1157
_refine_ls_wR_factor_ref         0.1181
_reflns_Friedel_coverage         0.764
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                5661
_reflns_number_total             5891
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            1920621.cif
_cod_data_source_block           sujuncheng_ehl-e-29
_cod_database_code               1552584
_shelx_shelxl_version_number     2016/6
_reflns_odcompleteness_completeness 90.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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), 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), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27),
 C30(H30), C31(H31), C32(H32), C33(H33), C34(H34)
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), C36(H36a,H36b,H36c), C38(H38a,H38b,H38c)
;
_shelx_res_checksum              78800
_shelx_hkl_checksum              91111
_olex2_date_sample_data_collection 1411352001.11
_olex2_submission_special_instructions 'No special instructions were received'