Rapid Access to Amino-Substituted Quinoline, (Di)Benzofuran, and Carbazole Heterocycles through an Aminobenzannulation Reaction
Martin Tiano; Philippe Belmont; Journal of Organic Chemistry 73 (2008) 4101–4109; doi:10.1021/jo800249f

data_4023432
_publ_contact_author_address
;Centre de Diffractom\'etrie Henri Longchambon
Universit\'e Claude Bernard Lyon1
43 boulevard du 11 novembre 1918
69622 Villeurbanne cedex
France
;
_publ_contact_author_email       erwann.jeanneau@univ-lyon1.fr
_publ_contact_author_fax         '+33 4 72 43 11 60'
_publ_contact_author_name        'Erwann Jeanneau'
_publ_contact_author_phone       '+33 4 72 43 18 59'
_publ_section_title
;
 Rapid Access to Amino-Substituted Quinoline, (Di)Benzofuran,
 and Carbazole Heterocycles through an Aminobenzannulation Reaction
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4101
_journal_page_last               4109
_journal_paper_doi               10.1021/jo800249f
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C22 H21 N1 O2'
_chemical_formula_sum            'C22 H21 N O2'
_chemical_formula_weight         331.4
_chemical_name_systematic
;
1-[2-(2-Phenyl-2-pyrrolidin-1-yl-vinyl)-benzofuran-3-yl]-ethanone
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             08-02-12
_audit_creation_method           CRYSTALS_ver_12.85
_cell_angle_alpha                90
_cell_angle_beta                 112.079(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.6895(8)
_cell_length_b                   9.5583(6)
_cell_length_c                   13.6237(9)
_cell_measurement_reflns_used    4088
_cell_measurement_temperature    295
_cell_measurement_theta_max      27.878
_cell_measurement_theta_min      0.730
_cell_volume                     1772.58(19)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1997-2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      295
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_device_type  Area
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.043
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7770
_diffrn_reflns_theta_full        27.028
_diffrn_reflns_theta_max         27.864
_diffrn_reflns_theta_min         1.496
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.21
_refine_diff_density_min         -0.18
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0229
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2398
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1176
_refine_ls_R_factor_gt           0.0470
_refine_ls_shift/su_max          0.000252
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 0.427 0.338 0.216 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1093
_refine_ls_wR_factor_gt          0.0487
_refine_ls_wR_factor_ref         0.0549
_reflns_limit_h_max              17
_reflns_limit_h_min              -19
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                1992
_reflns_number_total             4188
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   4.07
_oxford_diffrn_Wilson_scale      11.02
_oxford_refine_ls_r_factor_ref   0.0597
_oxford_refine_ls_scale          0.3370(8)
_oxford_reflns_number_all        4176
_oxford_reflns_threshold_expression_ref I>1.0\s(I)
_oxford_structure_analysis_title '1 P 1 21/a 1 R = New: P21/c'
_cod_data_source_file            jo800249f-File001.cif
_cod_data_source_block           1
_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/c 1 '
_cod_original_formula_sum        'C22 H21 N1 O2'
_cod_database_code               4023432