Iron-Catalyzed Skeletal Conversion of Lathyrane to Premyrsinane Euphorbia Diterpenes and Their Cytotoxic Activities
Xiao, Yao; Wang, Neng; Wan, Lin-Xi; Zhou, Xian-Li; Li, Xiaohuan; Gao, Feng; Journal of Natural Products  (2021) –; doi:10.1021/acs.jnatprod.0c01363

data_1562813
_publ_section_title
;
 Iron-Catalyzed Skeletal Conversion of Lathyrane to Premyrsinane Euphorbia
 Diterpenes and Their Cytotoxic Activities
;
_journal_name_full               'Journal of Natural Products'
_journal_paper_doi               10.1021/acs.jnatprod.0c01363
_journal_year                    2021
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C31 H40 O7'
_chemical_formula_sum            'C31 H40 O7'
_chemical_formula_weight         524.63
_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     iterative
_audit_creation_date             2020-09-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 102.494(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.4771(7)
_cell_length_b                   9.1278(7)
_cell_length_c                   15.7435(12)
_cell_measurement_reflns_used    1797
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.1280
_cell_measurement_theta_min      3.4950
_cell_volume                     1469.94(19)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.847
_diffrn_measurement_details
;
  1 omega    3.00   84.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       17.6648   57.0000   60.0000 81

  2 omega  -31.00   51.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -15.6336   57.0000  150.0000 82

  3 omega  -13.00   13.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -15.6336  -99.0000 -180.0000 26

  4 omega  -64.00  -38.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -15.6336 -178.0000  150.0000 26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0179246000
_diffrn_orient_matrix_UB_12      -0.0550650000
_diffrn_orient_matrix_UB_13      0.0321908000
_diffrn_orient_matrix_UB_21      -0.0040962000
_diffrn_orient_matrix_UB_22      0.0517970000
_diffrn_orient_matrix_UB_23      0.0328363000
_diffrn_orient_matrix_UB_31      -0.0668597000
_diffrn_orient_matrix_UB_32      -0.0180276000
_diffrn_orient_matrix_UB_33      -0.0036890000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0148
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.847
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7040
_diffrn_reflns_point_group_measured_fraction_full 0.759
_diffrn_reflns_point_group_measured_fraction_max 0.616
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.240
_diffrn_reflns_theta_min         3.092
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99763
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             564
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 786 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     369
_refine_ls_number_reflns         4926
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0869
_refine_ls_R_factor_gt           0.0534
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0549P)^2^+0.1392P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1118
_refine_ls_wR_factor_ref         0.1298
_reflns_Friedel_coverage         0.371
_reflns_Friedel_fraction_full    0.486
_reflns_Friedel_fraction_max     0.354
_reflns_number_gt                3341
_reflns_number_total             4926
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np0c01363_si_001.cif
_cod_data_source_block           200918_s2_xy
_cod_database_code               1562813
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         c12h12n2o3
_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
2. Uiso/Uaniso restraints and constraints
Uanis(C25) = Uanis(C25A)
Uanis(C24) = Uanis(C24A)
Uanis(C23) = Uanis(C23A)
Uanis(C22) = Uanis(C22A)
Uanis(C21) = Uanis(C21A)
Uanis(C20) = Uanis(C20A)
3. Others
 Sof(C20A)=Sof(C21A)=Sof(H21A)=Sof(C22A)=Sof(H22A)=Sof(C23A)=Sof(H23A)=
 Sof(C24A)=Sof(H24A)=Sof(C25A)=Sof(H25A)=1-FVAR(1)
 Sof(C20)=Sof(C21)=Sof(H21)=Sof(C22)=Sof(H22)=Sof(C23)=Sof(H23)=Sof(C24)=
 Sof(H24)=Sof(C25)=Sof(H25)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C12(H12), C13(H13), C14(H14)
4.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C8(H8A,H8B), C9(H9A,H9B)
4.c Aromatic/amide H refined with riding coordinates:
 C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C21A(H21A), C22A(H22A),
 C23A(H23A), C24A(H24A), C25A(H25A)
4.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C27(H27A,H27B,H27C), C28(H28A,H28B,
 H28C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C), C31(H31A,H31B,H31C)
;
_shelx_res_checksum              66240
_shelx_hkl_checksum              58616
_olex2_submission_special_instructions 'No special instructions were received'