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_1555946
_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 ad
_chemical_formula_moiety         'C20 H32 O3, 0.5(C6 H14)'
_chemical_formula_sum            'C23 H39 O3'
_chemical_formula_weight         363.54
_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     direct
_atom_sites_solution_secondary   difmap
_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                90.00
_cell_angle_beta                 92.7434(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.46386(6)
_cell_length_b                   20.34874(17)
_cell_length_c                   14.16918(13)
_cell_measurement_reflns_used    25858
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      72.4560
_cell_measurement_theta_min      2.1770
_cell_volume                     2149.55(3)
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      103(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.2417
_diffrn_detector_type            Onyx
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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   -118.00 -73.00   1.00    3.00    --  -44.02-125.00-180.00   45
  2  \w   -114.00 -18.00   1.00    3.00    --  -44.02 -57.00-120.00   96
  3  \w    -97.00  -2.00   1.00    3.00    --  -44.02 125.00 -60.00   95
  4  \w   -114.00 -18.00   1.00    3.00    --  -44.02 -57.00-180.00   96
  5  \w     73.00 118.00   1.00    3.00    --   44.02 125.00-120.00   45
  6  \w   -164.00 -59.00   1.00    7.50    --  -90.00 -76.00 -81.93  105
  7  \w   -162.00 -61.00   1.00    7.50    --  -90.00 -70.00-110.80  101
  8  \w   -164.00 -58.00   1.00    7.50    --  -90.00 -77.00-120.00  106
  9  \w   -160.00 -65.00   1.00    7.50    --  -90.00 -56.00-144.27   95
 10  \w     27.00 127.00   1.00    7.50    --  100.00 -30.00 -30.00  100
 11  \w     29.00 124.00   1.00    7.50    --  100.00 -45.00 120.00   95
 12  \w     21.00 139.00   1.00    7.50    --  100.00 -15.00  90.00  118
 13  \w     30.00 127.00   1.00    7.50    --  100.00 -61.00-120.00   97
 14  \w     26.00 132.00   1.00    7.50    --  100.00 -77.00  30.00  106
 15  \w     61.00 178.00   1.00    7.50    --  100.00  15.00  60.00  117
 16  \w     26.00 121.00   1.00    7.50    --  100.00-125.00 -60.00   95
 17  \w     73.00 170.00   1.00    7.50    --  100.00  61.00-150.00   97
 18  \w     26.00 121.00   1.00    7.50    --  100.00-125.00  30.00   95
 19  \w     68.00 144.00   1.00    7.50    --  100.00  77.00 -90.00   76
 20  \w     71.00 147.00   1.00    7.50    --  100.00  77.00-150.00   76
 21  \w     74.00 152.00   1.00    7.50    --  100.00  61.00-180.00   78
 22  \w    117.00 150.00   1.00    7.50    --  100.00  61.00 150.00   33
 23  \w    134.00 161.00   1.00    7.50    --  100.00  61.00  30.00   27
 24  \w    128.00 163.00   1.00    7.50    --  100.00  45.00 -60.00   35
 25  \w     71.00 120.00   1.00    7.50    --  100.00  77.00 150.00   49
 26  \w     77.00 170.00   1.00    7.50    --  100.00  45.00  90.00   93
 27  \w    108.00 173.00   1.00    7.50    --  100.00  77.00-180.00   65
 28  \w     68.00  95.00   1.00    7.50    --  100.00  77.00-180.00   27
 29  \w     78.00 123.00   1.00    7.50    --  100.00  61.00  30.00   45
 30  \w     93.00 121.00   1.00    7.50    --  100.00 -77.00-180.00   28
 31  \w     77.00 110.00   1.00    7.50    --  100.00  45.00 -60.00   33
 32  \w    107.00 134.00   1.00    7.50    --  100.00  30.00 -90.00   27
 33  \w    138.00 169.00   1.00    7.50    --  100.00  30.00 -90.00   31
 34  \w     58.00  88.00   1.00    7.50    --  100.00 -94.00  60.00   30
 35  \w     71.00 106.00   1.00    7.50    --  100.00 -94.00  90.00   35
 36  \w     27.00  60.00   1.00    7.50    --  100.00-125.00 120.00   33
 37  \w     68.00 171.00   1.00    7.50    --  100.00  77.00-120.00  103
 38  \w     62.00  89.00   1.00    7.50    --  100.00 -94.00 150.00   27
 39  \w     19.00  46.00   1.00    7.50    --  100.00 -94.00 150.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1983300000
_diffrn_orient_matrix_UB_12      0.0212920000
_diffrn_orient_matrix_UB_13      0.0073214000
_diffrn_orient_matrix_UB_21      -0.0314366000
_diffrn_orient_matrix_UB_22      0.0342756000
_diffrn_orient_matrix_UB_23      0.0947358000
_diffrn_orient_matrix_UB_31      0.0490070000
_diffrn_orient_matrix_UB_32      -0.0640475000
_diffrn_orient_matrix_UB_33      0.0530665000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            42952
_diffrn_reflns_theta_full        72.67
_diffrn_reflns_theta_max         72.67
_diffrn_reflns_theta_min         3.80
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           n/a
_diffrn_source_type              'Nova (Cu) X-ray Source'
_diffrn_source_voltage           n/a
_exptl_absorpt_coefficient_mu    0.559
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31225
_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_density_diffrn    1.123
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             804
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.05(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     481
_refine_ls_number_reflns         8471
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0482
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0909P)^2^+0.2780P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1327
_refine_ls_wR_factor_ref         0.1358
_reflns_number_gt                8077
_reflns_number_total             8471
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b03142_si_002.cif
_cod_data_source_block           lsn_160503
_cod_depositor_comments
;

2022-05-28
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C46 H78 O6'
_cod_original_formula_weight         727.08
_cod_original_formula_moiety         '2(C20 H32 O3), C6 H14'
_cod_original_formula_units_Z            2
_cod_database_code               1555946
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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:
 C1AA(H1AA), C15(H15), C21(H21), C22(H22), C24(H24), C26(H26)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C13(H13A,H13B), C2AA(H2AA,H2AB), C20(H20A,H20B), C23(H23A,H23B),
 C27(H27A,H27B), C28(H28A,H28B), C31(H31A,H31B), C33(H33A,H33B), C34(H34A,H34B),
  C36(H36A,H36B), C39(H39A,H39B), C42(H42A,H42B), C2(H2A,H2B), C7(H7A,H7B),
 C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4)
2.d Tetrahedral OH refined with riding coordinates:
 O0AA(H0AA), O3AA(H3AA)
2.e X=CH2 refined with riding coordinates:
 C5(H5A,H5B), C9(H9A,H9B)
2.f Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C25(H25A,H25B,H25C), C29(H29A,H29B,H29C), C30(H30A,H30B,
 H30C), C32(H32A,H32B,H32C), C37(H37A,H37B,H37C), C40(H40A,H40B,H40C), C43(H43A,
 H43B,H43C), C16(H16A,H16B,H16C), C0AA(H0AB,H0AC,H0AD)
2.g Idealised tetrahedral OH refined as rotating group:
 O3(H3), O6(H6)
;
_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 2.735
_oxdiff_exptl_absorpt_empirical_full_min 0.757