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_1562814
_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_formula_moiety         'C31 H40 O7'
_chemical_formula_sum            'C31 H40 O7'
_chemical_formula_weight         524.63
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2021-03-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9276(7)
_cell_length_b                   12.2037(7)
_cell_length_c                   21.9741(13)
_cell_measurement_reflns_used    1966
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.0220
_cell_measurement_theta_min      3.4560
_cell_volume                     2930.4(3)
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -11.00   18.40   0.7000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.6336  -99.0000    0.0000 42

  2 omega  -83.00   -2.50   0.7000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.6336  -77.0000  -60.0000 115

  3 omega  -16.00   22.50   0.7000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.6336  -99.0000 -180.0000 55
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0390383000
_diffrn_orient_matrix_UB_12      0.0380722000
_diffrn_orient_matrix_UB_13      -0.0148017000
_diffrn_orient_matrix_UB_21      0.0146930000
_diffrn_orient_matrix_UB_22      0.0238540000
_diffrn_orient_matrix_UB_23      0.0284881000
_diffrn_orient_matrix_UB_31      0.0497037000
_diffrn_orient_matrix_UB_32      -0.0369590000
_diffrn_orient_matrix_UB_33      0.0031713000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_unetI/netI     0.0553
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9024
_diffrn_reflns_point_group_measured_fraction_full 0.947
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.357
_diffrn_reflns_theta_min         3.114
_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  0.97017
_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    1.189
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.697
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 1052 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     357
_refine_ls_number_reflns         5601
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.1041
_refine_ls_R_factor_gt           0.0668
_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^)+(0.0856P)^2^+0.2811P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1561
_refine_ls_wR_factor_ref         0.1816
_reflns_Friedel_coverage         0.661
_reflns_Friedel_fraction_full    0.882
_reflns_Friedel_fraction_max     0.851
_reflns_number_gt                3674
_reflns_number_total             5601
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np0c01363_si_002.cif
_cod_data_source_block           210317_s2_xy
_cod_database_code               1562814
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         c12h12n2o3
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.971
_reflns_odcompleteness_completeness 99.68
_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. Restrained distances
 C10-C9A = C10-C9
 1.55 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C9) = Uanis(C9A)
Uanis(C8A) = Uanis(C8)
4. Others
 Sof(C8)=Sof(H8A)=Sof(H8B)=Sof(H10A)=Sof(C9A)=Sof(H9AA)=Sof(H9AB)=1-FVAR(1)
 Sof(C9)=Sof(H9A)=Sof(H9B)=Sof(H10)=Sof(C8A)=Sof(H8AA)=Sof(H8AB)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C10(H10A), C12(H12), C13(H13),
 C14(H14)
5.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C8(H8A,H8B), C9(H9A,H9B), C8A(H8AA,H8AB), C9A(H9AA,H9AB)
5.c Aromatic/amide H refined with riding coordinates:
 C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
5.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              50558
_shelx_hkl_checksum              69725
_olex2_submission_special_instructions 'No special instructions were received'