An investigation into the electrophilic cyclisation of N-acyl-pyrrolidinium ions: a facile synthesis of pyrrolo-tetrahydroisoquinolones and pyrrolo-benzazepinones
King, Frank D.; Aliev, Abil E.; Caddick, Stephen; Copley, Royston C. B.; Organic & Biomolecular Chemistry 7 (2009) 3561–3571; doi:10.1039/b907400g

data_7150704
_publ_section_title
;
 An investigation into the electrophilic cyclisation of
 N-acyl-pyrrolidinium ions: a facile synthesis of
 pyrrolo-tetrahydroisoquinolones and pyrrolo-benzazepinones
;
_journal_issue                   17
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              3561
_journal_page_last               3571
_journal_paper_doi               10.1039/b907400g
_journal_volume                  7
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H26 N2 O2'
_chemical_formula_sum            'C24 H26 N2 O2'
_chemical_formula_weight         374.47
_chemical_name_systematic
;
1-(Phenylacetyl)-4-[(2S)-1-(phenylacetyl)-2-pyrrolidinyl]-2,3-dihydro-1H-pyrrole
;
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.1731(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.12520(10)
_cell_length_b                   19.6810(2)
_cell_length_c                   9.80400(10)
_cell_measurement_reflns_used    1778
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      72.84
_cell_measurement_theta_min      4.49
_cell_volume                     983.19(2)
_computing_cell_refinement       'SMART V5.604 [NT] (Bruker, 2000)'
_computing_data_collection       'SMART V5.604 [NT] (Bruker, 2000)'
_computing_data_reduction        'SAINT+ V6.45A [NT] (Bruker, 2003)'
_computing_molecular_graphics    'SHELXTL V5.10 UNIX (Bruker, 1997)'
_computing_publication_material  'SHELXTL V6.10 UNIX (Bruker, 2001)'
_computing_structure_refinement  'SHELXTL V6.10 UNIX (Bruker, 2001)'
_computing_structure_solution    'SHELXTL V6.10 UNIX (Bruker, 2001)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_device_type  'Bruker AXS SMART 6000'
_diffrn_measurement_method       \w
_diffrn_radiation_collimation    '0.8 mm double-pinhole'
_diffrn_radiation_monochromator  'graphite - parallel geometry'
_diffrn_radiation_source         'normal focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0122
_diffrn_reflns_av_sigmaI/netI    0.0146
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9563
_diffrn_reflns_theta_full        73.28
_diffrn_reflns_theta_max         73.28
_diffrn_reflns_theta_min         4.49
_exptl_absorpt_coefficient_mu    0.636
_exptl_absorpt_correction_T_max  0.9629
_exptl_absorpt_correction_T_min  0.8922
_exptl_absorpt_correction_type   integration
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.05(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3747
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0304
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0554P)^2^+0.1087P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0813
_refine_ls_wR_factor_ref         0.0818
_reflns_number_gt                3692
_reflns_number_total             3747
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b907400g.txt
_cod_data_source_block           x4486b1
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7150704
_computing_data_merging          'SHELXTL V6.10 UNIX (Bruker, 2001)'