Semisynthetic Derivatives of Sesquiterpene Lactones by Palladium-Catalyzed Arylation of the α-Methylene-γ-lactone Substructure
Changho Han; Francis J. Barrios; Mark V. Riofski; David A. Colby; Journal of Organic Chemistry 74 (2009) 7176–7179; doi:10.1021/jo901533e

data_4024869
_publ_contact_author_address
;    Department of Chemistry
     Purdue University
     560 Oval Dr.
     W. Lafayette
     IN 47907-2084
     USA
;
_publ_contact_author_email       pfanwick@purdue.edu
_publ_contact_author_fax         1(765)4940239
_publ_contact_author_name        'Fanwick, Phillip E.'
_publ_contact_author_phone       1(765)4944572
_publ_section_title
;
Semisynthetic Derivatives of Sesquiterpene Lactones by Palladium-Catalyzed
Arylation of the \a-Methylene-\g-lactone Substructure
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7176
_journal_page_last               7179
_journal_paper_doi               10.1021/jo901533e
_journal_volume                  74
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H23 F3 O3,0.5(C1 H1 Cl3)'
_chemical_formula_sum            'C22.5 H23.5 Cl1.5 F3 O3'
_chemical_formula_weight         452.11
_space_group_IT_number           92
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4abw 2nw'
_symmetry_space_group_name_H-M   'P 41 21 2'
_atom_type_scat_source
'International Tables for Crystallography (Vol C)'
_audit_creation_date             13-05-09
_audit_creation_method           'SHELXL and local programs'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.19830(10)
_cell_length_b                   9.19830(10)
_cell_length_c                   51.2454(11)
_cell_measurement_reflns_used    3924
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      71
_cell_measurement_theta_min      3
_cell_volume                     4335.81(11)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1996)'
_computing_data_collection       'CrystalClear(Rigaku, 2001)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1996)'
_computing_molecular_graphics
;
    ORTEP (Johnson, 1976)
    PLATON (Spek, 1997)
;
_computing_publication_material  'SHELX97(Sheldrick, 2008) and local programs'
_computing_structure_refinement  'SHELX97 (Sheldrick, 2008)'
_computing_structure_solution
;
 Direct methods (SIR2004, Burla et al., 2005)
;
_diffrn_measured_fraction_theta_max 0.9274
_diffrn_measurement_device_type  Rigaku_Rapid_II
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  'confocal optics'
_diffrn_radiation_type           CU-K\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.038
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       62
_diffrn_reflns_limit_l_min       -61
_diffrn_reflns_number            16707
_diffrn_reflns_theta_max         71.91
_diffrn_reflns_theta_min         3.45
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.572
_exptl_absorpt_correction_T_max  0.7344
_exptl_absorpt_correction_T_min  0.4967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1976
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.34
_refine_diff_density_min         -0.45
_refine_ls_abs_structure_details 'Flack H. D. (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         3849
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.046
_refine_ls_R_factor_gt           0.046
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'1/[\s^2^(Fo^2^)+(0.0635P)^2^+2.4336P] where P=(Fo^2^+2Fc^2^)/3  '
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.118
_refine_ls_wR_factor_ref         0.118
_reflns_Friedel_coverage         0.7566
_reflns_number_gt                3821
_reflns_number_total             3849
_reflns_threshold_expression     >2.0\s(I)
_cod_data_source_file            jo901533e_si_001.cif
_cod_data_source_block           CH121
_cod_depositor_comments
;
The following automatic conversions were performed:
'_refine_ls_weighting_scheme' value 'calc ' changed to 'calc' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_formula_sum        'C22.50 H23.50 Cl1.50 F3 O3'
_cod_database_code               4024869