Cyclopropyl Alkynes as Mechanistic Probes to Distinguish Between Vinyl Radical and Ionic Intermediates
Gottschling, Stephen E.; Grant, Tina N.; Milnes, Kaarina K.; Jennings, Michael, C.; Baines, Kim M.; Journal of Organic Chemistry 70 (2005) 2686–2695; doi:10.1021/jo047797n

data_4020087
_publ_section_title
;
Cyclopropyl Alkynes as Mechanistic Probes to Distinguish
Between Vinyl Radical and Ionic Intermediates
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2686
_journal_page_last               2695
_journal_paper_doi               10.1021/jo047797n
_journal_volume                  70
_journal_year                    2005
_chemical_formula_sum            'C11 H9 Br O'
_chemical_formula_weight         237.09
_chemical_melting_point          78.5
_chemical_name_systematic
;
 1-bromo-3-phenylcyclopent-3-en-2-one
;
_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
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 100.6950(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.7665(3)
_cell_length_b                   11.2765(3)
_cell_length_c                   7.9422(2)
_cell_measurement_reflns_used    2740
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      30.03
_cell_measurement_theta_min      2.55
_cell_volume                     947.50(4)
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measurement_device_type  'Nonius Kappa-CCD'
_diffrn_measurement_method       '\f scans, and \w scans with \k offsets'
_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  0.064
_diffrn_reflns_av_sigmaI/netI    0.0526
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11704
_diffrn_reflns_theta_max         30.02
_diffrn_reflns_theta_min         2.64
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.291
_exptl_absorpt_correction_T_max  0.658
_exptl_absorpt_correction_T_min  0.282
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO-SMN (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.662
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'rectangular plate'
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.10
_refine_ls_extinction_coef       0.0058(18)
_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   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         2771
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0814
_refine_ls_R_factor_gt           0.0475
_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^)+(0.0742P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1193
_refine_ls_wR_factor_ref         0.1344
_reflns_number_gt                1853
_reflns_number_total             2771
_reflns_threshold_expression     I>2sigma(I)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4020087