Ebracpenes A and B, Unusual Ring C- seco and Ring D-aromatic Nor-Triterpenoids, from Euphorbia ebracteolata and Lipase Inhibitory Evaluation.
Wang, Chao; Yan, Qingsong; Wang, Yifei; Huang, Shanshan; Ning, Jing; Feng, Lei; Sun, Chengpeng; Zhang, Baojing; Li, Dawei; Ma, Xiaochi; The Journal of organic chemistry 84 (2019) 1624–1629; doi:10.1021/acs.joc.8b02800

data_4037553
_publ_section_title
;
 Ebracpenes A and B, Unusual Ring C- seco and Ring D-aromatic
 Nor-Triterpenoids, from Euphorbia ebracteolata and Lipase Inhibitory
 Evaluation.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1624
_journal_page_last               1629
_journal_paper_doi               10.1021/acs.joc.8b02800
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C29 H44 O2'
_chemical_formula_sum            'C29 H44 O2'
_chemical_formula_weight         424.64
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-09-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.4366(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.56339(13)
_cell_length_b                   7.68013(7)
_cell_length_c                   16.52524(11)
_cell_measurement_reflns_used    19531
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      73.3620
_cell_measurement_theta_min      2.6400
_cell_volume                     2478.44(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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_environment      N~2~
_diffrn_ambient_temperature      99.98(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_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   -113.00 -13.00   1.00    1.00    --  -40.98 -57.00 -60.00  100
  2  \w   -115.00 -16.00   1.00    1.00    --  -40.98 -38.00 -60.00   99
  3  \w   -115.00 -16.00   1.00    1.00    --  -40.98 -38.00-180.00   99
  4  \w      8.00 117.00   1.00    1.00    --   40.98  77.00  60.00  109
  5  \w      1.00  82.00   1.00    1.00    --   40.98 -99.00  90.00   81
  6  \w      1.00  82.00   1.00    1.00    --   40.98 -99.00 150.00   81
  7  \w     13.00 113.00   1.00    1.00    --   40.98  57.00 -30.00  100
  8  \w     23.00  97.00   1.00    1.00    --   40.98-125.00 -90.00   74
  9  \w     74.00 178.00   1.00    1.80    --  106.95  77.00 -30.00  104
 10  \w     78.00 178.00   1.00    1.80    --  106.95  61.00 -60.00  100
 11  \w     34.00 121.00   1.00    1.80    --  106.95-125.00 150.00   87
 12  \w    101.00 178.00   1.00    1.80    --  106.95 107.00  45.00   77
 13  \w     74.00 178.00   1.00    1.80    --  106.95  77.00  30.00  104
 14  \w     25.00 109.00   1.00    1.80    --  106.95 -95.00  30.00   84
 15  \w     78.00 178.00   1.00    1.80    --  106.95  61.00   0.00  100
 16  \w     74.00 178.00   1.00    1.80    --  106.95  77.00   0.00  104
 17  \w     78.00 178.00   1.00    1.80    --  106.95  61.00 -30.00  100
 18  \w     34.00 121.00   1.00    1.80    --  106.95-125.00 -60.00   87
 19  \w     78.00 178.00   1.00    1.80    --  106.95  61.00  30.00  100
 20  \w     74.00 178.00   1.00    1.80    --  106.95  77.00 -90.00  104
 21  \w     81.00 178.00   1.00    1.80    --  106.95  45.00 -30.00   97
 22  \w     81.00 178.00   1.00    1.80    --  106.95  45.00  30.00   97
 23  \w     74.00 178.00   1.00    1.80    --  106.95  77.00 -60.00  104
 24  \w     81.00 178.00   1.00    1.80    --  106.95  45.00   0.00   97
 25  \w     81.00 178.00   1.00    1.80    --  106.95  45.00  60.00   97
 26  \w     81.00 178.00   1.00    1.80    --  106.95  45.00  90.00   97
 27  \w     78.00 178.00   1.00    1.80    --  106.95  61.00  60.00  100
 28  \w     74.00 178.00   1.00    1.80    --  106.95  77.00 120.00  104
 29  \w    -69.00  32.00   1.00    1.00    --  -40.98  57.00  60.00  101
 30  \w   -117.00  -8.00   1.00    1.00    --  -40.98 -77.00  60.00  109
 31  \w   -117.00  -8.00   1.00    1.00    --  -40.98 -77.00 150.00  109
 32  \w    -39.00 -13.00   1.00    1.00    --  -41.23 -57.00 -30.00   26
 33  \w   -117.00  -9.00   1.00    1.00    --  -41.23 -77.00-120.00  108
 34  \w   -113.00 -13.00   1.00    1.00    --  -41.23 -57.00 120.00  100
 35  \w   -113.00 -13.00   1.00    1.00    --  -41.23 -57.00-180.00  100
 36  \w      1.00  82.00   1.00    1.00    --   41.23 -99.00 -90.00   81
 37  \w      0.00 121.00   1.00    1.00    --   41.23  19.00-150.00  121
;
_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      0.0762849000
_diffrn_orient_matrix_UB_12      -0.0491293000
_diffrn_orient_matrix_UB_13      0.0120380000
_diffrn_orient_matrix_UB_21      -0.0055388000
_diffrn_orient_matrix_UB_22      0.0024633000
_diffrn_orient_matrix_UB_23      0.0926170000
_diffrn_orient_matrix_UB_31      -0.0193457000
_diffrn_orient_matrix_UB_32      -0.1944045000
_diffrn_orient_matrix_UB_33      -0.0018622000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            25397
_diffrn_reflns_point_group_measured_fraction_full 0.955
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.640
_diffrn_reflns_theta_min         2.679
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.524
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70005
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.138
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 1928 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4713
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0379
_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^)+(0.0548P)^2^+1.7108P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1036
_refine_ls_wR_factor_ref         0.1042
_reflns_Friedel_coverage         0.753
_reflns_Friedel_fraction_full    0.902
_reflns_Friedel_fraction_max     0.877
_reflns_number_gt                4599
_reflns_number_total             4713
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02800_si_002.cif
_cod_data_source_block           11q_1
_cod_database_code               4037553
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C9(H9), C2(H2A), C3(H3), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C1(H1A,H1B), C6(H6A,H6B), C7(H7A,H7B), C12(H12A,H12B),
 C19(H19A,H19B), C21(H21A,H21B), C22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C15(H15)
2.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C23(H23A,H23B,H23C), C27(H27A,H27B,
 H27C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_olex2_date_sample_data_collection 2018-09-10
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.057
_oxdiff_exptl_absorpt_empirical_full_min 0.709