Syntheses and Biological Evaluation of Costunolide, Parthenolide, and Their Fluorinated Analogues.
Yang, Zhong-Jin; Ge, Wei-Zhi; Li, Qiu-Ying; Lu, Yaxin; Gong, Jian-Miao; Kuang, Bei-Jia; Xi, Xiaonan; Wu, Haiting; Zhang, Quan; Chen, Yue; Journal of medicinal chemistry 58 (2015) 7007–7020; doi:10.1021/acs.jmedchem.5b00915

data_1529429
_publ_section_title
;
 Syntheses and Biological Evaluation of Costunolide, Parthenolide, and
 Their Fluorinated Analogues.
;
_journal_issue                   17
_journal_name_full               'Journal of medicinal chemistry'
_journal_page_first              7007
_journal_page_last               7020
_journal_paper_doi               10.1021/acs.jmedchem.5b00915
_journal_volume                  58
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H17 F3 O3'
_chemical_formula_sum            'C15 H17 F3 O3'
_chemical_formula_weight         302.28
_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-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.511(4)
_cell_length_b                   11.945(6)
_cell_length_c                   14.173(7)
_cell_measurement_reflns_used    1183
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      42.30
_cell_measurement_theta_min      6.10
_cell_volume                     1440.9(12)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b42'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b42'
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       \w
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_unetI/netI     0.0134
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14966
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         77.691
_diffrn_reflns_theta_min         6.065
_exptl_absorpt_coefficient_mu    1.045
_exptl_absorpt_correction_T_max  0.901
_exptl_absorpt_correction_T_min  0.702
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.128
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details
; 
 Flack x determined using 1212 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.02(2)
_refine_ls_extinction_coef       0.0013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3034
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0268
_refine_ls_R_factor_gt           0.0254
_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^)+(0.0303P)^2^+0.2584P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0657
_refine_ls_wR_factor_ref         0.0667
_reflns_Friedel_coverage         0.725
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                2906
_reflns_number_total             3034
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jm5b00915_si_002.cif
_cod_data_source_block           shelxl
_cod_depositor_comments          'Adding full bibliography for 1529429.cif.'
_cod_database_code               1529429
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.787
_shelx_estimated_absorpt_t_max   0.903
_shelx_res_checksum              10013
_shelx_hkl_checksum              19133