Secoheliosphanes A and B and secoheliospholane A, three diterpenoids with unusual seco-jatrophane and seco-jatropholane skeletons from Euphorbia helioscopia.
Mai, Zhen-Peng; Ni, Gang; Liu, Yan-Fei; Li, Yu-Huan; Li, Li; Li, Jia-Yuan; Yu, De-Quan; The Journal of organic chemistry  (2017) –; doi:10.1021/acs.joc.7b02558

data_4033278
_publ_section_title
;
 Secoheliosphanes A and B and secoheliospholane A, three diterpenoids with
 unusual seco-jatrophane and seco-jatropholane skeletons from Euphorbia
 helioscopia.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.7b02558
_journal_year                    2017
_chemical_formula_moiety         'C31 H40 O10'
_chemical_formula_sum            'C31 H40 O10'
_chemical_formula_weight         572.63
_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_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-04-17
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.37266(19)
_cell_length_b                   12.3721(3)
_cell_length_c                   28.5539(7)
_cell_measurement_reflns_used    4429
_cell_measurement_temperature    103.5
_cell_measurement_theta_max      70.9507
_cell_measurement_theta_min      3.8906
_cell_volume                     2957.82(12)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_diffrn_ambient_temperature      103.5
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details
;
  1 omega  -52.00    7.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  111.0000  -60.0000 59

  2 omega  -28.00   54.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -77.0000  120.0000 82

  3 omega  -17.00   35.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -89.0000   82.0000 52

  4 omega   19.00  105.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   37.0000  -90.0000 86

  5 omega   10.00   36.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -37.0000 -120.0000 26

  6 omega  121.00  168.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   60.0000 47

  7 omega   44.00   89.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 45

  8 omega   41.00   73.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 32

  9 omega  137.00  169.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  120.0000 32

 10 omega   93.00  119.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  120.0000 26

 11 omega   40.00   91.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 51

 12 omega   98.00  172.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -60.0000 74

 13 omega   39.00  177.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000  -90.0000 138
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1301708000
_diffrn_orient_matrix_UB_12      -0.0872627000
_diffrn_orient_matrix_UB_13      -0.0049328000
_diffrn_orient_matrix_UB_21      0.0883507000
_diffrn_orient_matrix_UB_22      0.0714061000
_diffrn_orient_matrix_UB_23      -0.0357886000
_diffrn_orient_matrix_UB_31      0.0951974000
_diffrn_orient_matrix_UB_32      0.0531210000
_diffrn_orient_matrix_UB_33      0.0400415000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0466
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            10223
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.089
_diffrn_reflns_theta_min         3.894
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.792
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86128
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 2096 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         5555
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0378
_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^)+(0.0471P)^2^+0.2329P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0918
_refine_ls_wR_factor_ref         0.0944
_reflns_Friedel_coverage         0.736
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.955
_reflns_number_gt                5254
_reflns_number_total             5555
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02558_si_002.cif
_cod_data_source_block           exp_4852
_cod_original_cell_volume        2957.83(12)
_cod_database_code               4033278
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_shelx_estimated_absorpt_t_max   0.932
_shelx_estimated_absorpt_t_min   0.742
_shelx_hkl_checksum              10828
_shelx_res_checksum              36394
_shelx_shelxl_version_number     2014/7