Allenyl Azide Cycloaddition Chemistry: Exploration of the Scope and Mechanism of Cyclopentennelated Dihydropyrrole Synthesis through Azatrimethylenemethane Intermediates
Ken S. Feldman; Malliga R. Iyer; Carlos Silva López; Olalla Nieto Faza; Journal of Organic Chemistry 73 (2008) 5090–5099; doi:10.1021/jo8008066

data_4023523
_publ_section_title
;
 Allenyl Azide Cycloaddition Chemistry: Exploration of the Scope
 and Mechanism of Cyclopentennelated Dihydropyrrole
 Synthesis through Azatrimethylenemethane Intermediates
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5090
_journal_page_last               5099
_journal_paper_doi               10.1021/jo8008066
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C14 H14 Br N'
_chemical_formula_sum            'C14 H14 Br N'
_chemical_formula_weight         276.17
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                85.140(17)
_cell_angle_beta                 79.187(19)
_cell_angle_gamma                78.799(17)
_cell_formula_units_Z            2
_cell_length_a                   7.433(8)
_cell_length_b                   7.991(8)
_cell_length_c                   10.455(11)
_cell_measurement_reflns_used    2783
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      28.241
_cell_measurement_theta_min      2.843
_cell_volume                     597.6(11)
_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      133(2)
_diffrn_measured_fraction_theta_full 0.96
_diffrn_measured_fraction_theta_max 0.898
_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
_diffrn_reflns_av_R_equivalents  0.0591
_diffrn_reflns_av_sigmaI/netI    0.1088
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4946
_diffrn_reflns_theta_full        28.47
_diffrn_reflns_theta_max         28.47
_diffrn_reflns_theta_min         1.99
_exptl_absorpt_coefficient_mu    3.410
_exptl_absorpt_correction_T_max  0.760
_exptl_absorpt_correction_T_min  0.701
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.453
_refine_diff_density_min         -1.009
_refine_diff_density_rms         0.176
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         3003
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.987
_refine_ls_R_factor_all          0.0998
_refine_ls_R_factor_gt           0.0693
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1202P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1759
_refine_ls_wR_factor_ref         0.2091
_reflns_number_gt                1766
_reflns_number_total             2703
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8008066-File005.cif
_cod_data_source_block           mxr7s
_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.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4023523