Zn(OTf)~2~-Catalyzed Cyclization of Proparyl Alcohols with Anilines, Phenols, and Amides for Synthesis of Indoles, Benzofurans, and Oxazoles through Different Annulation Mechanisms
Manyam Praveen Kumar; Rai-Shung Liu; Journal of Organic Chemistry 71 (2006) 4951–4955; doi:10.1021/jo0606711

data_4021767
_publ_section_title
;
 Zn(OTf)~2~-Catalyzed Cyclization of Proparyl Alcohols with Anilines,
 Phenols, and Amides for Synthesis of Indoles, Benzofurans,
 and Oxazoles through Different Annulation Mechanisms
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4951
_journal_page_last               4955
_journal_paper_doi               10.1021/jo0606711
_journal_volume                  71
_journal_year                    2006
_chemical_formula_sum            'C16 H15 N'
_chemical_formula_weight         221.29
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.603(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.5552(1)
_cell_length_b                   7.6732(1)
_cell_length_c                   12.5769(2)
_cell_measurement_reflns_used    2654
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.16
_cell_measurement_theta_min      3.12
_cell_volume                     625.492(16)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and 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  0.0414
_diffrn_reflns_av_sigmaI/netI    0.0426
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6370
_diffrn_reflns_theta_max         26.38
_diffrn_reflns_theta_min         1.64
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  0.97427
_exptl_absorpt_correction_T_min  0.88376
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       Columnar
_exptl_crystal_F_000             236
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   6(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     153
_refine_ls_number_reflns         2435
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.990
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0397
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0660P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0908
_refine_ls_wR_factor_ref         0.1136
_reflns_number_gt                1847
_reflns_number_total             2435
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0606711si20060330_012502.cif
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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      'P 21'
_cod_database_code               4021767