Euphomilones A and B, ent-Rosane Diterpenoids with 7/5/6 and 5/7/6 Skeletons from Euphorbia milii.
Liu, Shao-Nan; Huang, Dane; Morris-Natschke, Susan L; Ma, Hang; Liu, Zhi-Hong; Seeram, Navindra P.; Xu, Jun; Lee, Kuo-Hsiung; Gu, Qiong; Organic letters 18 (2016) 6132–6135; doi:10.1021/acs.orglett.6b03142

data_1555947
_publ_section_title
;
 Euphomilones A and B, ent-Rosane Diterpenoids with 7/5/6 and 5/7/6
 Skeletons from Euphorbia milii.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              6132
_journal_page_last               6135
_journal_paper_doi               10.1021/acs.orglett.6b03142
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C20 H32 O3'
_chemical_formula_sum            'C20 H32 O3'
_chemical_formula_weight         320.48
_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'
_symmetry_Int_Tables_number      19
_atom_sites_solution_primary     direct
_audit_creation_date             2016-10-20
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.47780(4)
_cell_length_b                   9.96312(6)
_cell_length_c                   24.19049(16)
_cell_measurement_reflns_used    14070
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      70.8430
_cell_measurement_theta_min      4.7880
_cell_volume                     1802.245(19)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.9888
_diffrn_measured_fraction_theta_max 0.9888
_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    -70.00  31.00   1.00    1.00    --  -41.89  57.00  90.00  101
  2  \w   -116.00 -17.00   1.00    1.00    --  -41.89 -38.00 -90.00   99
  3  \w    100.00 178.00   1.00    1.00    --  101.33  98.00 105.00   78
  4  \w     94.00 175.00   1.00    1.00    --  101.33 125.00 -60.00   81
  5  \w     25.00 130.00   1.00    1.00    --  101.33 -30.00 -60.00  105
  6  \w     28.00 121.00   1.00    1.00    --  101.33-125.00   0.00   93
  7  \w     13.00 178.00   1.00    1.00    --  101.33   0.00 150.00  165
  8  \w   -118.00  -9.00   1.00    1.00    --  -41.89 -77.00  60.00  109
  9  \w   -118.00  -9.00   1.00    1.00    --  -41.89 -77.00-180.00  109
 10  \w     72.00 174.00   1.00    1.00    --  101.33  61.00 -90.00  102
 11  \w     69.00 177.00   1.00    1.00    --  101.33  77.00-150.00  108
 12  \w     75.00 174.00   1.00    1.00    --  101.33  45.00 -30.00   99
 13  \w     25.00  84.00   1.00    1.00    --  101.33 -77.00  30.00   59
 14  \w     69.00 177.00   1.00    1.00    --  101.33  77.00   0.00  108
;
_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      -0.1171466000
_diffrn_orient_matrix_UB_12      0.1043424000
_diffrn_orient_matrix_UB_13      0.0299634000
_diffrn_orient_matrix_UB_21      -0.1557254000
_diffrn_orient_matrix_UB_22      -0.1011679000
_diffrn_orient_matrix_UB_23      0.0015613000
_diffrn_orient_matrix_UB_31      0.0668542000
_diffrn_orient_matrix_UB_32      -0.0527887000
_diffrn_orient_matrix_UB_33      0.0561745000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_unetI/netI     0.0120
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            16267
_diffrn_reflns_theta_full        70.9477
_diffrn_reflns_theta_max         70.95
_diffrn_reflns_theta_min         4.80
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.606
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48420
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_colour_primary    colorless
_exptl_crystal_density_diffrn    1.1810
_exptl_crystal_description       block
_exptl_crystal_F_000             706.0888
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.4588
_refine_diff_density_min         -0.3880
_refine_diff_density_rms         0.0423
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.08(12)
_refine_ls_d_res_high            0.8156
_refine_ls_d_res_low             9.2124
_refine_ls_goodness_of_fit_ref   1.0660
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    46
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3435
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0660
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0331
_refine_ls_shift/su_max          0.0009
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0524P)^2^+0.5013P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0889
_refine_ls_wR_factor_ref         0.0891
_reflns_Friedel_coverage         0.983
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              12
_reflns_limit_k_min              -12
_reflns_limit_l_max              29
_reflns_limit_l_min              -28
_reflns_number_gt                3404
_reflns_number_total             3435
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            ol6b03142_si_003.cif
_cod_data_source_block           1606012
_cod_original_cell_volume        1802.244(19)
_cod_original_sg_symbol_Hall     ' P 2ac 2ab'
_cod_database_code               1555947
_chemical_oxdiff_formula         'C20 H20 O4'
_chemical_oxdiff_usercomment     t11c6
_reflns_odcompleteness_completeness 99.83
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4a,H4b), C5(H5a,H5b), C8(H8a,H8b), C9(H9a,H9b), C10(H10a,H10b), C11(H11a,
 H11b), C12(H12a,H12b), C18(H18a,H18b)
2.c Aromatic/amide H refined with riding coordinates:
 C19(H19)
2.d Tetrahedral OH refined with riding coordinates:
 O1(H1), O2(H2)
2.e Idealised Me refined as rotating group:
 C15(H15a,H15b,H15c), C16(H16a,H16b,H16c), C23(H23a,H23b,H23c)
;
_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 2.004
_oxdiff_exptl_absorpt_empirical_full_min 0.763