Intramolecularipso-Halocyclization of 4-(p-Unsubstituted-aryl)-1-alkynes Leading to Spiro[4,5]trienones: Scope, Application, and Mechanistic Investigations
Bo-Xiao Tang; Yue-Hua Zhang; Ren-Jie Song; Dong-Jun Tang; Guo-Bo Deng; Zhi-Qiang Wang; Ye-Xiang Xie; Yuan-Zhi Xia; Jin-Heng Li; Journal of Organic Chemistry 77 (2012) 2837–2849; doi:10.1021/jo300037n

data_4027079
_publ_section_title
;
 Intramolecularipso-Halocyclization of 4-(p-Unsubstituted-aryl)-1-alkynes
 Leading to Spiro[4,5]trienones: Scope, Application, and Mechanistic
 Investigations
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2837
_journal_page_last               2849
_journal_paper_doi               10.1021/jo300037n
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C22 H14 Br N O2'
_chemical_formula_weight         404.25
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.106(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.7473(7)
_cell_length_b                   9.6146(10)
_cell_length_c                   27.114(3)
_cell_measurement_reflns_used    3397
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      51.939
_cell_measurement_theta_min      4.497
_cell_volume                     1752.0(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_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  0.0498
_diffrn_reflns_av_sigmaI/netI    0.0596
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            10198
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.25
_exptl_absorpt_coefficient_mu    2.362
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7568
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.492
_exptl_crystal_size_mid          0.423
_exptl_crystal_size_min          0.381
_refine_diff_density_max         0.686
_refine_diff_density_min         -0.600
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       0.0309(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.910
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3984
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.910
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0394
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0454P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0851
_refine_ls_wR_factor_ref         0.0882
_reflns_number_gt                2867
_reflns_number_total             3984
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo300037n_si_002.cif
_cod_data_source_block           cd28604
_cod_database_code               4027079