Stereoselective Synthesis of 3,3-Diarylacrylonitriles as Tubulin Polymerization Inhibitors
Zhenglai Fang; Yunlong Song; Taradas Sarkar; Ernest Hamel; William E. Fogler; Gregory E. Agoston; Phillip E. Fanwick; Mark Cushman; Journal of Organic Chemistry 73 (2008) 4241–4244; doi:10.1021/jo800428b

data_4023449
_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        'Phillip E. Fanwick'
_publ_contact_author_phone       1(765)4944572
_publ_section_title
;
 Stereoselective Synthesis of 3,3-Diarylacrylonitriles
 as Tubulin Polymerization Inhibitors
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4241
_journal_page_last               4244
_journal_paper_doi               10.1021/jo800428b
_journal_volume                  73
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C12 H10 F3 N1 O5 S1'
_chemical_formula_sum            'C12 H10 F3 N O5 S'
_chemical_formula_weight         337.28
_chemical_name_systematic        ' ?'
_space_group_IT_number           161
_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_Hall  'R 3 -2"c'
_symmetry_space_group_name_H-M   'R 3 c :H'
_atom_type_scat_source
'International Tables for Crystallography (Vol C)'
_audit_creation_date             6-04-07
_audit_creation_method           'SHELXL and local programs'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            18
_cell_length_a                   31.351(4)
_cell_length_b                   31.351(4)
_cell_length_c                   7.6711(13)
_cell_measurement_reflns_used    10963
_cell_measurement_temperature    150
_cell_measurement_theta_max      24
_cell_measurement_theta_min      3
_cell_volume                     6529.8(17)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1996)'
_computing_data_collection       'Collect (Nonius, 1998)'
_computing_data_reduction        'EVALCCD (Duisenberg, 2003)'
_computing_molecular_graphics
;
    ORTEP (Johnson, 1976)
    PLATON (Spek, 1997)
;
_computing_publication_material  'SHELX97(Sheldrick, 1997) and local programs'
_computing_structure_refinement  'SHELX97 (Sheldrick, 1997)'
_computing_structure_solution
;
 Direct methods (SIR2004, Burla et al., 2005)
;
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_max 0.8777
_diffrn_measurement_device_type  Nonius_KappaCCD
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  'graphite 002'
_diffrn_radiation_type           MO-K\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.061
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            10963
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         3.05
_exptl_absorpt_coefficient_mu    0.267
_exptl_absorpt_correction_T_max  0.9802
_exptl_absorpt_correction_T_min  0.8427
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick 1996)'
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             3096
_exptl_crystal_size_max          0.63
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.69
_refine_diff_density_min         -0.48
_refine_ls_abs_structure_details
'Flack H. D. (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_d_res_high            0.89
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2096
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.078
_refine_ls_R_factor_gt           0.069
_refine_ls_shift/su_max          0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'1/[\s^2^(Fo^2^)+(0.0773P)^2^+57.5439P] where P=(Fo^2^+2Fc^2^)/3 '
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.164
_refine_ls_wR_factor_ref         0.171
_reflns_Friedel_coverage         1.0000
_reflns_number_gt                1882
_reflns_number_total             2096
_reflns_threshold_expression     >2.0\s(I)
_cod_data_source_file            jo800428b-File004_1.cif
_cod_data_source_block           11
_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_sg_symbol_H-M      'R 3 c'
_cod_original_formula_sum        'C12 H10 F3 N1 O5 S1'
_cod_database_code               4023449