Trifluoroacetylation-Induced Houben-Hoesch-Type Cyclization of Cyanoacetanilides: Increased Nucleophilicity of CN Groups
Yusuke Kobayashi; Kosuke Katagiri; Isao Azumaya; Takashi Harayama; Journal of Organic Chemistry 75 (2010) 2741–2744; doi:10.1021/jo100220m

data_4025361
_publ_contact_author_address
;Tokushima Bunri University
Shido 1314-1, Sanuki, Kagawa, Japan
;
_publ_contact_author_email       ykobayashi@kph.bunri-u.ac.jp
_publ_contact_author_fax         '+81 87 894 0181'
_publ_contact_author_name        'Yusuke Kobayashi'
_publ_contact_author_phone       '+81 87 894 5111'
_publ_section_title
;
 Trifluoroacetylation-Induced Houben-Hoesch-Type Cyclization of
 Cyanoacetanilides: Increased Nucleophilicity of CN Groups
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2741
_journal_page_last               2744
_journal_paper_doi               10.1021/jo100220m
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C12 H12 N2 O2'
_chemical_formula_weight         216.24
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                89.029(15)
_cell_angle_beta                 75.838(17)
_cell_angle_gamma                85.883(17)
_cell_formula_units_Z            2
_cell_length_a                   7.095(9)
_cell_length_b                   8.508(11)
_cell_length_c                   9.717(13)
_cell_measurement_reflns_used    1992
_cell_measurement_temperature    120
_cell_measurement_theta_max      28.08
_cell_measurement_theta_min      2.40
_cell_volume                     567.3(13)
_computing_cell_refinement       'Smart (Bruker AXS)'
_computing_data_collection       'Smart (Bruker AXS)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.857
_diffrn_measurement_device_type  'Bruker Smart1000 CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_sigmaI/netI    0.0438
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3242
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         2.16
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9869
_exptl_absorpt_correction_T_min  0.9656
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             228
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.552
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.179
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2414
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.179
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0642
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0866P)^2^+0.9234P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2146
_refine_ls_wR_factor_ref         0.2193
_reflns_number_gt                2091
_reflns_number_total             2414
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo100220m_si_002.cif
_cod_data_source_block           0014kka
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        567.2(13)
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               4025361