Ring Contraction of Bridgehead Sultams by Photoinduced Di-π-methane Rearrangement
Robert D. Dura; Leo A. Paquette; Journal of Organic Chemistry 71 (2006) 2456–2459; doi:10.1021/jo0526587

data_4021587
_publ_section_title
;
 Ring Contraction of Bridgehead Sultams by Photoinduced
 Di-\p-methane Rearrangement
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2456
_journal_page_last               2459
_journal_paper_doi               10.1021/jo0526587
_journal_volume                  71
_journal_year                    2006
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C10 H9 Br2 N1 O2 S1'
_chemical_formula_sum            'C10 H9 Br2 N O2 S'
_chemical_formula_weight         367.06
_chemical_name_common            'Paquette 1399'
_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     heavy
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2005-12-13T17:20:53-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 111.078(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1336(10)
_cell_length_b                   8.6732(10)
_cell_length_c                   12.5840(10)
_cell_measurement_reflns_used    2782
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.037
_cell_measurement_wavelength     0.71073
_cell_volume                     1133.86(19)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_type       'by Nonius Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      -0.283816E-1
_diffrn_orient_matrix_UB_12      0.683933E-1
_diffrn_orient_matrix_UB_13      -0.685608E-1
_diffrn_orient_matrix_UB_21      0.71235E-1
_diffrn_orient_matrix_UB_22      -0.408385E-1
_diffrn_orient_matrix_UB_23      -0.22768E-1
_diffrn_orient_matrix_UB_31      -0.581874E-1
_diffrn_orient_matrix_UB_32      -0.833555E-1
_diffrn_orient_matrix_UB_33      -0.450994E-1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.040
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            23767
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         2.92
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    7.316
_exptl_absorpt_correction_T_max  0.249
_exptl_absorpt_correction_T_min  0.195
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'HKL Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.15
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'triangular  chunk'
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.704
_refine_diff_density_min         -0.835
_refine_diff_density_rms         0.152
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.168
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2605
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.168
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0346
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
' w=1/[\s^2^(Fo^2^)+(0.0458P)^2^+0.7110P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0816
_refine_ls_wR_factor_ref         0.0857
_reflns_number_gt                2250
_reflns_number_total             2605
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0526587si20051227_031816.cif
_cod_original_sg_symbol_H-M      ' P 21/c'
_cod_database_code               4021587