Phytotoxic ent-Isopimarane-Type Diterpenoids from Euphorbia hylonoma.
Wei, Wen-Jun; Song, Qiu-Yan; Zheng, Zai-Qin; Yao, Xiaojun; Li, Ya; Gao, Kun; Journal of natural products 81 (2018) 2381–2391; doi:10.1021/acs.jnatprod.8b00365

data_1553384
_publ_section_title
;
 Phytotoxic ent-Isopimarane-Type Diterpenoids from Euphorbia hylonoma.
;
_journal_issue                   11
_journal_name_full               'Journal of natural products'
_journal_page_first              2381
_journal_page_last               2391
_journal_paper_doi               10.1021/acs.jnatprod.8b00365
_journal_volume                  81
_journal_year                    2018
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C20 H30 O4, H2 O'
_chemical_formula_sum            'C20 H32 O5'
_chemical_formula_weight         352.45
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2018-01-10
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 98.677(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.0078(9)
_cell_length_b                   6.8749(8)
_cell_length_c                   12.6547(12)
_cell_measurement_reflns_used    606
_cell_measurement_temperature    296.56(10)
_cell_measurement_theta_max      21.4540
_cell_measurement_theta_min      3.7340
_cell_volume                     946.72(16)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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_temperature      296.56(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega   -7.00   19.00   2.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  -99.0000    0.0000 13

  2 omega   70.00  100.00   2.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  178.0000 -180.0000 15

  3 omega  -48.00   72.00   2.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867    0.0000  -90.0000 60

  4 omega   49.00  105.00   2.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867 -178.0000    0.0000 28
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0105127000
_diffrn_orient_matrix_UB_12      0.0630459000
_diffrn_orient_matrix_UB_13      -0.0420230000
_diffrn_orient_matrix_UB_21      0.0162407000
_diffrn_orient_matrix_UB_22      -0.0810949000
_diffrn_orient_matrix_UB_23      -0.0296703000
_diffrn_orient_matrix_UB_31      -0.0622197000
_diffrn_orient_matrix_UB_32      -0.0104519000
_diffrn_orient_matrix_UB_33      -0.0237896000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_unetI/netI     0.1019
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3645
_diffrn_reflns_point_group_measured_fraction_full 0.703
_diffrn_reflns_point_group_measured_fraction_max 0.696
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.007
_diffrn_reflns_theta_min         3.257
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.08642
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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    1.236
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 246 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -3.1(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         2594
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.1126
_refine_ls_R_factor_gt           0.0631
_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^)+(0.0421P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1134
_refine_ls_wR_factor_ref         0.1435
_reflns_Friedel_coverage         0.282
_reflns_Friedel_fraction_full    0.348
_reflns_Friedel_fraction_max     0.336
_reflns_number_gt                1512
_reflns_number_total             2594
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np8b00365_si_001.cif
_cod_data_source_block           ch_1_25_15
_cod_database_code               1553384
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H O N'
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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, All O(H,H) groups
2.a Free rotating group:
 O5(H5A,H5B)
2.b Ternary CH refined with riding coordinates:
 C3(H3A), C5(H5), C9(H9), C11(H11), C12(H12)
2.c Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C6(H6A,H6B), C14(H14A,H14B)
2.d Aromatic/amide H refined with riding coordinates:
 C7(H7), C15(H15)
2.e X=CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.f Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C)
2.g Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3)
;
_shelx_res_checksum              1620
_shelx_hkl_checksum              54180
_olex2_date_sample_data_collection 2017-05-23
_olex2_submission_special_instructions 'No special instructions were received'