Concise Synthesis of α-Substituted 2-Benzofuranmethamines and other 2-Subsituted Benzofurans via α-Substituted 2-Benzofuranmethyl Carbocation Intermediates
Nikhom Wongsa; Ubonta Sommart; Thunwadee Ritthiwigrom; Arife Yazici; Somdej Kanokmedhakul; Kwanjai Kanokmedhakul; Anthony C. Willis; Stephen G. Pyne; Journal of Organic Chemistry 78 (2013) 1138–1148; doi:10.1021/jo302554v

data_4027927
_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
;
 Concise Synthesis of \a-Substituted 2-Benzofuranmethamines and other
 2-Subsituted Benzofurans via \a-Substituted 2-Benzofuranmethyl
 Carbocation Intermediates
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1138
_journal_page_last               1148
_journal_paper_doi               10.1021/jo302554v
_journal_volume                  78
_journal_year                    2013
_chemical_compound_source        ' from U of Wollongong '
_chemical_formula_moiety         'C25 H29 N O3'
_chemical_formula_sum            'C25 H29 N O3'
_chemical_formula_weight         391.51
_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
_audit_creation_date             12-08-21
_audit_creation_method           CRYSTALS_ver_14.11
_audit_update_record
;
2012-08-22 - Report C25 H29 N O3
             by Anthony C. Willis
             for Steve Pyne

2012-08-22 - pass checkcif tests with minor warnings  
2012-11-21 - prepare cif for deposit to CCDC
;
_cell_angle_alpha                109.3316(12)
_cell_angle_beta                 111.7524(13)
_cell_angle_gamma                99.3681(13)
_cell_formula_units_Z            2
_cell_length_a                   10.3220(2)
_cell_length_b                   10.6609(2)
_cell_length_c                   11.5882(2)
_cell_measurement_reflns_used    13955
_cell_measurement_temperature    200
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.6
_cell_volume                     1056.67(4)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
; 
ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997)
;
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      200
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       Area
_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  0.027
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            22906
_diffrn_reflns_theta_full        27.475
_diffrn_reflns_theta_max         27.475
_diffrn_reflns_theta_min         2.550
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.967
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
via gaussian method (Coppens, 1970) implemented in maXus (2000)
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_description       block
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.34
_refine_diff_density_min         -0.17
_refine_ls_extinction_coef       290(20)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   0.9840
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     350
_refine_ls_number_reflns         4827
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0391
_refine_ls_shift/su_max          0.0026607
_refine_ls_shift/su_mean         0.0002593
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 0.30P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1051
_refine_ls_wR_factor_gt          0.1006
_refine_ls_wR_factor_ref         0.1051
_reflns_limit_h_max              12
_reflns_limit_h_min              -13
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                4182
_reflns_number_total             4827
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.89
_oxford_diffrn_Wilson_scale      0.25
_oxford_refine_ls_r_factor_ref   0.0455
_oxford_refine_ls_scale          2.031(16)
_oxford_reflns_number_all        4827
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title '8211700 pyn1206'
_cod_data_source_file            jo302554v_si_001.cif
_cod_data_source_block           pyn1206
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               4027927
_iucr_refine_instruction_details_constraints
;
BLOCK 
CONT SCALE 
CONT C    (    1 ,X'S,U'S)  UNTIL C    (   29 ) 
CONT H    (   11 ,X'S)  UNTIL H    (  293 ) 
CONT EXTPARAM 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;