Direct Comparison of the Response of Bicyclic Sultam and Lactam Dienes to Photoexcitation. Concerning the Propensity of Differing Bond Types to Bridgehead Nitrogen for Homolytic Cleavage
Leo A. Paquette; Robert D. Dura; Nathan Fosnaugh; Marshall Stepanian; Journal of Organic Chemistry 71 (2006) 8438–8445; doi:10.1021/jo061404y

data_4022042
_publ_section_title
;
 Direct Comparison of the Response of Bicyclic Sultam
 and Lactam Dienes to Photoexcitation. Concerning the Propensity of
 Differing Bond Types to Bridgehead Nitrogen for Homolytic Cleavage
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8438
_journal_page_last               8445
_journal_paper_doi               10.1021/jo061404y
_journal_volume                  71
_journal_year                    2006
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C12 H11 N1 O2 S1'
_chemical_formula_sum            'C12 H11 N O2 S'
_chemical_formula_weight         233.28
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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             2006-06-28T11:13:31-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 100.395(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.460(2)
_cell_length_b                   11.070(2)
_cell_length_c                   17.536(3)
_cell_measurement_reflns_used    2045
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.028
_cell_measurement_theta_min      2.037
_cell_measurement_wavelength     0.71073
_cell_volume                     2188.1(7)
_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-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi and omega scans'
_diffrn_orient_matrix_type       'by Nonius Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      -0.620041E-1
_diffrn_orient_matrix_UB_12      0.630924E-1
_diffrn_orient_matrix_UB_13      -0.161004E-1
_diffrn_orient_matrix_UB_21      0.406922E-1
_diffrn_orient_matrix_UB_22      0.246006E-1
_diffrn_orient_matrix_UB_23      -0.434358E-1
_diffrn_orient_matrix_UB_31      -0.486858E-1
_diffrn_orient_matrix_UB_32      -0.597902E-1
_diffrn_orient_matrix_UB_33      -0.348612E-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  0.034
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17060
_diffrn_reflns_reduction_process
;
 Scaled and merged with SORTAV
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.36
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    0.278
_exptl_absorpt_correction_T_max  0.967
_exptl_absorpt_correction_T_min  0.931
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'rhombus-shaped plate'
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.23
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.06(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         3757
_refine_ls_number_restraints     16
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0416
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0518P)^2^+2.4879P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0982
_refine_ls_wR_factor_ref         0.1023
_reflns_number_gt                3338
_reflns_number_total             3757
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo061404ysi20060629_015854.cif
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               4022042