Unexpected σ Bond Rupture during the Reaction of N-Methyl-1,2,4-triazoline-3,5-dione with Acenaphthylene and Indene.
Breton, Gary W.; Hughes, Joshua S.; Pitchko, Timothy J.; Martin, Kenneth L.; Hardcastle, Kenneth; The Journal of organic chemistry 79 (2014) 8212–8220; doi:10.1021/jo5014096

data_4029853
_publ_section_title
;
 Unexpected \s Bond Rupture during the Reaction of
 N-Methyl-1,2,4-triazoline-3,5-dione with Acenaphthylene and Indene.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8212
_journal_page_last               8220
_journal_paper_doi               10.1021/jo5014096
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C15 H11 N3 O3'
_chemical_formula_sum            'C15 H11 N3 O3'
_chemical_formula_weight         281.27
_chemical_name_common            'Compound 16'
_space_group_IT_number           12
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 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                 101.990(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.3950(5)
_cell_length_b                   12.8325(5)
_cell_length_c                   7.9578(3)
_cell_measurement_reflns_used    1258
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      67.34
_cell_measurement_theta_min      5.02
_cell_volume                     1238.14(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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      173(2)
_diffrn_measured_fraction_theta_full 0.947
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0794
_diffrn_reflns_av_sigmaI/netI    0.0546
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3864
_diffrn_reflns_theta_full        69.48
_diffrn_reflns_theta_max         69.48
_diffrn_reflns_theta_min         5.02
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.900
_exptl_absorpt_correction_T_max  0.9315
_exptl_absorpt_correction_T_min  0.8129
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irreg
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       0.0010(2)
_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   1.041
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1158
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0416
_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^)+(0.0480P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1006
_refine_ls_wR_factor_ref         0.1033
_reflns_number_gt                933
_reflns_number_total             1158
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5014096_si_004.cif
_cod_data_source_block           GB1_2011
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 4029852--4029854.cif.
;
_cod_original_cell_volume        1238.14(8)
_cod_original_sg_symbol_H-M      C2/m
_cod_database_code               4029853