Nucleophile-Induced Intramolecular Dipole 1,5-Transfer and 1,6-Cyclization: Experimental and ab Initio Studies of Formation, Thermolysis, and Molecular and Electronic Structures of 3,6-Diphenyl-1-propanesulfenimido-1,2,4,5-tetrazine
Piotr Kaszynski; Victor G. Young; Journal of the American Chemical Society 122 (2000) 2087–2095; doi:10.1021/ja993884z

data_4115948
_publ_section_title
;
 Nucleophile-Induced Intramolecular Dipole 1,5-Transfer and
 1,6-Cyclization: Experimental and ab Initio Studies of Formation,
 Thermolysis, and Molecular and Electronic Structures of
 3,6-Diphenyl-1-propanesulfenimido-1,2,4,5-tetrazine
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2087
_journal_page_last               2095
_journal_paper_doi               10.1021/ja993884z
_journal_volume                  122
_journal_year                    2000
_chemical_compound_source        'Prof. P. Kaszynski - Vanderbilt University'
_chemical_formula_sum            'C17 H17 N5 S'
_chemical_formula_weight         323.42
_chemical_name_common            99003a
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 90.666(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.8294(4)
_cell_length_b                   13.6781(9)
_cell_length_c                   17.5898(12)
_cell_measurement_temperature    173(2)
_cell_volume                     1643.01(18)
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_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  0.0281
_diffrn_reflns_av_sigmaI/netI    0.0334
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            12172
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         1.89
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.858
_exptl_absorpt_correction_type   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            Orangish-yellow
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_description       Needle
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.031
_refine_ls_goodness_of_fit_obs   1.140
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2895
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_restrained_S_obs      1.140
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_obs          0.0323
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0426P)^2^+0.1039P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0819
_refine_ls_wR_factor_obs         0.0775
_reflns_number_observed          2176
_reflns_number_total             2895
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ja993884z.cif
_cod_data_source_block           99003a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0426P)^2^+0.1039P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0426P)^2^+0.1039P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1643.0(2)
_cod_database_code               4115948