Protection-Group-Free Semisyntheses of Parthenolide and Its Cyclopropyl Analogue
Jing Long; Ya-Hui Ding; Pan-Pan Wang; Quan Zhang; Yue Chen; Journal of Organic Chemistry 78 (2013) 10512–10518; doi:10.1021/jo401606q

data_4028662
_publ_section_title
;
 Protection-Group-Free Semisyntheses of Parthenolide and Its Cyclopropyl
 Analogue
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10512
_journal_page_last               10518
_journal_paper_doi               10.1021/jo401606q
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C15 H20 O3'
_chemical_formula_sum            'C15 H20 O3'
_chemical_formula_weight         248.31
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.9456(11)
_cell_length_b                   12.2757(12)
_cell_length_c                   18.780(2)
_cell_measurement_reflns_used    2963
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.80
_cell_measurement_theta_min      27.70
_cell_volume                     2753.9(5)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r5'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r5'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 11.11
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Rigaku Saturn944 CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0673
_diffrn_reflns_av_sigmaI/netI    0.0386
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            28278
_diffrn_reflns_theta_full        72.78
_diffrn_reflns_theta_max         72.78
_diffrn_reflns_theta_min         4.30
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.660
_exptl_absorpt_correction_T_max  0.9017
_exptl_absorpt_correction_T_min  0.8683
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   CrystalClear
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_description       prism
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.117
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_coef       0.0435(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         5400
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0737
_refine_ls_R_factor_gt           0.0683
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0953P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1403
_refine_ls_wR_factor_ref         0.1499
_reflns_number_gt                4597
_reflns_number_total             5400
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401606q_si_002.cif
_cod_data_source_block           shelxl
_cod_database_code               4028662