Total syntheses of parthenolide and its analogues with macrocyclic stereocontrol.
Long, Jing; Zhang, Shan-Feng; Wang, Pan-Pan; Zhang, Xue-Mei; Yang, Zhong-Jin; Zhang, Quan; Chen, Yue; Journal of medicinal chemistry 57 (2014) 7098–7112; doi:10.1021/jm5009456

data_1517410
_publ_section_title
;
 Total syntheses of parthenolide and its analogues with macrocyclic
 stereocontrol.
;
_journal_issue                   16
_journal_name_full               'Journal of medicinal chemistry'
_journal_page_first              7098
_journal_page_last               7112
_journal_paper_doi               10.1021/jm5009456
_journal_volume                  57
_journal_year                    2014
_chemical_formula_moiety         'C15 H20 O3'
_chemical_formula_sum            'C15 H20 O3'
_chemical_formula_weight         248.31
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.1945(19)
_cell_length_b                   10.289(2)
_cell_length_c                   21.907(5)
_cell_measurement_reflns_used    1475
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.00
_cell_measurement_theta_min      27.50
_cell_volume                     1396.2(6)
_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-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 11.11
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Rigaku Saturn944 CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0824
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            22114
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         72.385
_diffrn_reflns_theta_min         4.036
_exptl_absorpt_coefficient_mu    0.651
_exptl_absorpt_correction_T_max  0.949
_exptl_absorpt_correction_T_min  0.737
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.181
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.084
_refine_ls_abs_structure_details
; 
 Flack x determined using 787 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.10(11)
_refine_ls_extinction_coef       0.103(6)
_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   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2705
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0618
_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^)+(0.0881P)^2^] 
 where P=(Fo^2^+2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1276
_refine_ls_wR_factor_ref         0.1322
_reflns_Friedel_coverage         0.696
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                2270
_reflns_number_total             2705
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jm5009456_si_002.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
'Adding full bibliography for 1517409--1517410.cif.'
_cod_database_code               1517410
_shelx_estimated_absorpt_t_min   0.926
_shelx_estimated_absorpt_t_max   0.950
_shelxl_version_number           2013-2
_shelx_res_checksum              20665
_shelx_hkl_checksum              58706