Dicyano(7,7-dimethyl-2,5-di-<i>p</i>-tolyl-3,4-diazabicyclo[4.1.0]hepta-2,4-dien-3-ium-3-yl)methanide and (4-Benzoyl-5,5-dimethyl-2-phenyl-1-azacyclopenta-1,3-dien-1-ium-1-yl)dicyanomethanide, Two Stable Azomethine Ylides
Breu, J.; Range, K.-J.; Riebel, P.; Weber, A.; Sauer, J.; Acta Crystallographica Section C 52 (1996) 2053–2056; doi:10.1107/S0108270196001084

data_2005254
_publ_section_title
;Dicyano(7,7-dimethyl-2,5-di-<i>p</i>-tolyl-3,4-diazabicyclo[4.1.0]hepta-2,4-dien-3-ium-3-yl)methanide
 and
 (4-Benzoyl-5,5-dimethyl-2-phenyl-1-azacyclopenta-1,3-dien-1-ium-1-yl)dicyanomethanide,
 Two Stable Azomethine Ylides
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              2053
_journal_page_last               2056
_journal_paper_doi               10.1107/S0108270196001084
_journal_volume                  52
_journal_year                    1996
_chemical_formula_sum            'C24 H22 N4'
_chemical_formula_weight         366.47
_chemical_name_systematic
;
 Dicyano[7,7-dimethyl-2,5-di-p-tolyl-3,4-diazabicyclo[4.1.0]
 hept-2,4-diene-3-ium-3-yl]methanide
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                71.47(1)
_cell_angle_beta                 76.13(1)
_cell_angle_gamma                75.27(1)
_cell_formula_units_Z            2
_cell_length_a                   9.364(1)
_cell_length_b                   10.457(1)
_cell_length_c                   11.311(2)
_cell_measurement_reflns_used    1258
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      24.20
_cell_measurement_theta_min      1.93
_cell_volume                     1000.3(2)
_computing_molecular_graphics    'PLATON (Spek, 1990) and PLUTON (Spek, 1991)'
_computing_publication_material  PLATON
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      170(2)
_diffrn_measurement_device       'STOE IPDS'
_diffrn_measurement_method       rotation
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0706
_diffrn_reflns_av_sigmaI/netI    0.1335
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5870
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_max         24.20
_diffrn_reflns_theta_min         1.93
_exptl_absorpt_coefficient_mu    0.07
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange--red
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.180
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   0.970
_refine_ls_goodness_of_fit_obs   1.392
_refine_ls_hydrogen_treatment
'refall, except for methyl H atoms which were refined as riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         3008
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.310
_refine_ls_restrained_S_obs      1.392
_refine_ls_R_factor_all          0.1440
_refine_ls_R_factor_obs          0.0574
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
;
calc w = 1/[U\s^2^(F~o~^2^) + (0.0285P)^2^]
where P = (F~o~^2^ + 2F~c~^2^)/3
;
_refine_ls_wR_factor_all         0.1442
_refine_ls_wR_factor_obs         0.0947
_reflns_number_observed          1301
_reflns_number_total             3010
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            jz1114.cif
_cod_data_source_block           III
_cod_original_cell_volume        1000.2(3)
_cod_original_formula_sum        ' C24 H22 N4'
_cod_database_code               2005254