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_4021768
_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            'C17 H15 N O'
_chemical_formula_weight         249.30
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
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_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                79.7810(10)
_cell_angle_beta                 88.2520(10)
_cell_angle_gamma                82.9250(10)
_cell_formula_units_Z            4
_cell_length_a                   7.3484(2)
_cell_length_b                   10.8617(3)
_cell_length_c                   17.3118(5)
_cell_measurement_reflns_used    4769
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2.5
_cell_volume                     1349.43(7)
_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      273(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
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_diffrn_reflns_av_sigmaI/netI    0.0651
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
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_diffrn_reflns_theta_max         28.09
_diffrn_reflns_theta_min         1.20
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.95040
_exptl_absorpt_correction_T_min  0.62389
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            yello
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       lamellar
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_ls_extinction_coef       0.022(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
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_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1631P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2410
_refine_ls_wR_factor_ref         0.2831
_reflns_number_gt                2835
_reflns_number_total             6539
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0606711si20060330_012542.cif
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Empirical' changed to
'empirical' 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 

The following automatic conversions were performed:

'_refine_ls_hydrogen_treatment' value 'contr' was replaced with the
value 'constr' as specified in the replacement file
'src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5376 2017-05-30 11:51:03Z andrius 
;
_cod_database_code               4021768