Metal-Catalyzed Cycloisomerization Reactions of cis-4-Hydroxy-5-alkynylpyrrolidinones and cis-5-Hydroxy-6-alkynylpiperidinones: Synthesis of Furo[3,2-b]pyrroles and Furo[3,2-b]pyridines
Jasmine C. Jury; Nalivela Kumara Swamy; Arife Yazici; Anthony C. Willis; Stephen G. Pyne; Journal of Organic Chemistry 74 (2009) 5523–5527; doi:10.1021/jo9007942

data_4024687
_publ_contact_author_address
;
Research School of Chemistry,
The Australian National University,
Canberra, A. C. T. 0200, Australia
;
_publ_contact_author_email       ' willis@rsc.anu.edu.au '
_publ_contact_author_fax         ' 61 2 6125 0750 '
_publ_contact_author_name        ' Anthony C. Willis '
_publ_contact_author_phone       ' 61 2 6125 4109 '
_publ_section_title
;
Metal-Catalyzed Cycloisomerization Reactions
of cis-4-Hydroxy-5-alkynylpyrrolidinones
and cis-5-Hydroxy-6-alkynylpiperidinones: Synthesis of Furo[3,2-b]pyrroles
and Furo[3,2-b]pyridines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5523
_journal_page_last               5527
_journal_paper_doi               10.1021/jo9007942
_journal_volume                  74
_journal_year                    2009
_chemical_compound_source        ' from UoW '
_chemical_formula_moiety         'C18 H25 N O3 Si'
_chemical_formula_sum            'C18 H25 N O3 Si'
_chemical_formula_weight         331.49
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             08-04-04
_audit_creation_method           CRYSTALS_ver_12.18
_audit_update_record
;
2008-04-04 - Report on C18 H25 N O3 Si
             by Anthony C. Willis
             for  Jasmine Jury and Steve Pyne

2008-04-04 - passes checkcif tests with no warnings  
;
_cell_angle_alpha                90
_cell_angle_beta                 92.3403(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.0847(2)
_cell_length_b                   8.9796(1)
_cell_length_c                   15.6906(3)
_cell_measurement_reflns_used    21764
_cell_measurement_temperature    200
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.6
_cell_volume                     1842.04(5)
_computing_cell_refinement       'Denzo/Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius BV, 1997)'
_computing_data_reduction        'Denzo/Scalepack (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
; 
ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997)
;
_computing_publication_material  'CRYSTALS (Watkin et al 2003)'
_computing_structure_refinement  'CRYSTALS (Watkin et al 2003)'
_computing_structure_solution    'SIR92 (Altomare et al, 1994)'
_diffrn_ambient_temperature      200
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       ' \f and \w scans with CCD '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.040
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            36549
_diffrn_reflns_theta_full        27.507
_diffrn_reflns_theta_max         27.507
_diffrn_reflns_theta_min         2.598
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.141
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.931
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
via Gaussian method (Coppens, 1970) implemented in maXus (2000)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_density_meas      ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.28
_refine_diff_density_min         -0.25
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9169
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0337
_refine_ls_shift/su_max          0.010485
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 0.05P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0937
_refine_ls_wR_factor_gt          0.0906
_refine_ls_wR_factor_ref         0.0937
_reflns_limit_h_max              16
_reflns_limit_h_min              -16
_reflns_limit_k_max              11
_reflns_limit_k_min              0
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                3162
_reflns_number_total             4223
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.82
_oxford_diffrn_Wilson_scale      1.19
_oxford_refine_ls_scale          0.965(3)
_oxford_structure_analysis_title '4040907 wol0801'
_cod_data_source_file            jo9007942_si_001.cif
_cod_data_source_block           wol0801
_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 1 21/a 1 '
_cod_database_code               4024687