#------------------------------------------------------------------------------ #$Date: 2012-02-03 17:16:24 +0000 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/52/2005254.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2005254 loop_ _publ_author_name 'Breu, J.' 'Range, K.-J.' 'Riebel, P.' 'Weber, A.' 'Sauer, J.' _publ_section_title ;Dicyano(7,7-dimethyl-2,5-di-p-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_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) _[local]_cod_data_source_file jz1114.cif _[local]_cod_data_source_block III _[local]_cod_chemical_formula_sum_orig ' C24 H22 N4' _cod_original_cell_volume 1000.2(3) _cod_database_code 2005254 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z loop_ _atom_site_label _atom_site_occupancy _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type N3 1 -0.2143(3) 1.0398(3) .3901(3) .056(1) Uani N5 1 -0.1556(3) .8526(3) .0884(3) .0556(2) Uani N12 1 .2040(3) .8593(3) .1209(3) .043(1) Uani N13 1 .1212(3) .9557(3) .1868(3) .043(1) Uani C1 1 -.0352(4) .9529(4) .2110(4) .0438(2) Uani C2 1 -0.1294(4) 1.0014(4) .3092(4) .0436(2) Uani C4 1 -.0921(4) .8967(4) .1397(4) .0442(2) Uani C6 1 .4039(4) .8643(4) .3083(4) .043(1) Uani C7 1 .5341(4) .8669(4) .3659(4) .0555(2) Uani C8 1 .3054(4) .7660(4) .3931(4) .0511(2) Uani C11 1 .3494(4) .8394(4) .1028(4) .041(1) Uani C14 1 .1799(4) 1.0404(4) .2174(4) .041(1) Uani C15 1 .3379(4) 1.0045(4) .2280(4) .0428(2) Uani C16 1 .4338(4) .8903(4) .1649(4) .0422(2) Uani C21 1 .4278(4) .7639(4) .0093(4) .0411(2) Uani C22 1 .5756(4) .6912(4) .0109(4) .045(1) Uani C23 1 .6457(4) .6182(4) -.0772(4) .046(1) Uani C24 1 .5748(4) .6194(4) -0.1728(4) .048(1) Uani C25 1 .4285(4) .6966(4) -0.1775(4) .0535(2) Uani C26 1 .3559(4) .7668(4) -.0869(4) .046(1) Uani C27 1 .6485(4) .5394(4) -0.2677(4) .0618(2) Uani C31 1 .0911(4) 1.1678(4) .2458(4) .042(1) Uani C32 1 -.0032(4) 1.2627(4) .1652(4) .044(1) Uani C33 1 -.0789(4) 1.3841(4) .1923(4) .0509(2) Uani C34 1 -.0708(4) 1.4132(4) .3024(4) .0537(2) Uani C35 1 .0237(4) 1.3171(4) .3821(4) .0540(2) Uani C36 1 .1056(4) 1.1976(4) .3535(4) .044(1) Uani C37 1 -0.1602(4) 1.5418(4) .3389(4) .0824(2) Uani H7A 1 .597(2) .7771(7) .383(2) .077(5) Uiso H7B 1 .4958(4) .893(2) .443(1) .077(5) Uiso H7C 1 .592(2) .932(2) .3075(9) .077(5) Uiso H8A 1 .263(2) .792(1) .4702(9) .077(5) Uiso H8B 1 .3641(6) .6745(5) .412(2) .077(5) Uiso H8C 1 .227(1) .769(2) .3511(8) .077(5) Uiso H15 1 .381(3) 1.080(3) .212(3) .046(8) Uiso H16 1 .537(3) .888(3) .126(3) .046(8) Uiso H22 1 .628(3) .690(3) .091(3) .058(4) Uiso H23 1 .761(3) .565(3) -.073(3) .058(4) Uiso H25 1 .376(3) .711(4) -0.242(4) .058(4) Uiso H26 1 .246(3) .831(3) -.090(3) .058(4) Uiso H27A 1 .668(3) .6019(4) -0.3502(7) .148(9) Uiso H27B 1 .583(2) .482(2) -0.269(2) .148(9) Uiso H27C 1 .741(2) .483(3) -0.245(2) .148(9) Uiso H32 1 -.007(3) 1.244(3) .070(3) .058(4) Uiso H33 1 -0.155(3) 1.447(3) .144(3) .058(4) Uiso H35 1 .035(4) 1.329(4) .458(3) .058(4) Uiso H36 1 .185(3) 1.126(3) .415(3) .058(4) Uiso H37A 1 -.0938(6) 1.589(2) .355(3) .148(9) Uiso H37B 1 -0.233(2) 1.5170(5) .414(2) .148(9) Uiso H37C 1 -0.211(3) 1.601(2) .271(1) .148(9) Uiso loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 N3 0.046(2) 0.066(2) 0.060(3) -0.014(2) -0.007(2) -0.021(2) N5 0.051(2) 0.071(3) 0.048(3) -0.017(2) 0.000(2) -0.023(2) N12 0.039(2) 0.043(2) 0.049(2) -0.0041(14) -0.004(2) -0.021(2) N13 0.034(2) 0.045(2) 0.048(2) -0.0021(15) -0.004(2) -0.015(2) C1 0.034(2) 0.062(3) 0.042(3) -0.012(2) -0.004(2) -0.023(2) C2 0.040(2) 0.052(3) 0.043(3) -0.010(2) -0.010(2) -0.016(2) C4 0.037(2) 0.046(3) 0.044(3) -0.005(2) 0.001(2) -0.013(2) C6 0.041(2) 0.041(2) 0.044(3) -0.006(2) -0.004(2) -0.012(2) C7 0.046(2) 0.067(3) 0.059(3) -0.003(2) -0.016(2) -0.026(2) C8 0.057(2) 0.051(3) 0.043(3) -0.008(2) -0.003(2) -0.016(2) C11 0.038(2) 0.041(2) 0.043(3) -0.004(2) -0.006(2) -0.012(2) C14 0.040(2) 0.041(2) 0.047(3) -0.007(2) -0.008(2) -0.018(2) C15 0.032(2) 0.039(3) 0.055(3) -0.008(2) -0.003(2) -0.012(2) C16 0.038(2) 0.048(3) 0.043(3) -0.008(2) 0.001(2) -0.022(2) C21 0.036(2) 0.048(3) 0.042(3) -0.008(2) -0.004(2) -0.018(2) C22 0.040(2) 0.050(2) 0.045(3) -0.005(2) -0.006(2) -0.016(2) C23 0.041(2) 0.045(2) 0.049(3) -0.006(2) -0.005(2) -0.012(2) C24 0.043(2) 0.044(2) 0.056(3) -0.010(2) 0.005(2) -0.020(2) C25 0.055(3) 0.051(3) 0.051(3) -0.006(2) -0.010(2) -0.012(2) C26 0.043(2) 0.046(2) 0.052(3) -0.007(2) -0.009(2) -0.019(2) C27 0.058(2) 0.066(3) 0.065(3) -0.005(2) 0.001(2) -0.037(3) C31 0.038(2) 0.042(2) 0.045(3) -0.004(2) -0.008(2) -0.015(2) C32 0.042(2) 0.045(2) 0.045(3) -0.004(2) -0.006(2) -0.016(2) C33 0.043(2) 0.049(3) 0.058(3) 0.001(2) -0.011(2) -0.017(2) C34 0.047(2) 0.037(2) 0.073(4) -0.003(2) -0.003(2) -0.019(2) C35 0.055(3) 0.061(3) 0.051(3) -0.015(2) -0.004(2) -0.023(3) C36 0.042(2) 0.043(2) 0.050(3) -0.007(2) -0.005(2) -0.020(2) C37 0.090(3) 0.056(3) 0.092(4) 0.001(2) 0.004(3) -0.034(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag N13 N12 C11 118.1(3) yes N12 N13 C1 110.6(3) yes N12 N13 C14 124.3(3) yes C1 N13 C14 125.0(3) yes N13 C1 C2 119.7(4) yes N13 C1 C4 120.2(4) yes C2 C1 C4 120.0(4) yes N3 C2 C1 176.4(4) yes N5 C4 C1 172.3(4) yes C7 C6 C8 113.7(3) no C7 C6 C15 113.4(3) no C7 C6 C16 115.8(3) no C8 C6 C15 121.3(3) no C8 C6 C16 121.4(4) no C15 C6 C16 61.6(3) yes N12 C11 C16 124.6(4) yes N12 C11 C21 115.1(4) yes C16 C11 C21 120.3(4) yes N13 C14 C15 119.1(4) yes N13 C14 C31 122.6(4) yes C15 C14 C31 118.2(4) yes C6 C15 C14 120.9(4) yes C6 C15 C16 59.3(3) yes C14 C15 C16 115.3(3) yes C6 C16 C11 121.4(4) yes C6 C16 C15 59.2(3) yes C11 C16 C15 113.8(3) yes C11 C21 C22 121.8(4) no C11 C21 C26 119.7(4) no C22 C21 C26 118.5(4) no C21 C22 C23 120.4(4) no C22 C23 C24 121.5(4) no C23 C24 C25 118.1(4) no C23 C24 C27 122.1(4) no C25 C24 C27 119.8(4) no C24 C25 C26 120.6(4) no C21 C26 C25 120.8(4) no C14 C31 C32 121.9(4) no C14 C31 C36 118.9(4) no C32 C31 C36 119.2(4) no C31 C32 C33 119.9(4) no C32 C33 C34 121.7(4) no C33 C34 C35 117.5(4) no C33 C34 C37 123.0(4) no C35 C34 C37 119.5(4) no C34 C35 C36 121.4(4) no C31 C36 C35 120.1(4) no C6 C7 H7A 109.3(10) no C6 C7 H7B 109.4(6) no C6 C7 H7C 109.5(9) no H7A C7 H7B 109.6(2) no H7A C7 H7C 109.4(2) no H7B C7 H7C 109.6(13) no C6 C8 H8A 109.5(10) no C6 C8 H8B 109.5(8) no C6 C8 H8C 109.5(8) no H8A C8 H8B 109.4(14) no H8A C8 H8C 109.5(14) no H8B C8 H8C 109.5(12) no C6 C15 H15 121(2) no C14 C15 H15 113(2) no C16 C15 H15 115(2) no C6 C16 H16 114.8(2) no C11 C16 H16 114.0(2) no C15 C16 H16 123.5(2) no C21 C22 H22 116.0(2) no C23 C22 H22 123.4(2) no C22 C23 H23 117.6(2) no C24 C23 H23 120.8(2) no C24 C25 H25 124(2) no C26 C25 H25 115(2) no C21 C26 H26 116.4(2) no C25 C26 H26 122.7(2) no C24 C27 H27A 109.5(5) no C24 C27 H27B 109.6(13) no C24 C27 H27C 109.4(14) no H27A C27 H27B 109.5(2) no H27A C27 H27C 109(2) no H27B C27 H27C 109(2) no C31 C32 H32 119.7(2) no C33 C32 H32 120.1(2) no C32 C33 H33 121.7(2) no C34 C33 H33 115.7(2) no C34 C35 H35 123(3) no C36 C35 H35 116(3) no C31 C36 H36 119.7(2) no C35 C36 H36 120.2(2) no C34 C37 H37A 109.5(12) no C34 C37 H37B 109.5(6) no C34 C37 H37C 109.4(10) no H37A C37 H37B 109(2) no H37A C37 H37C 110(2) no H37B C37 H37C 109.3(2) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag N3 C2 1.163(5) yes N5 C4 1.174(5) yes N12 N13 1.406(4) yes N12 C11 1.299(5) yes N13 C1 1.430(5) yes N13 C14 1.319(5) yes C1 C2 1.389(6) yes C1 C4 1.395(6) yes C6 C7 1.523(6) no C6 C8 1.503(6) no C6 C15 1.523(6) yes C6 C16 1.524(6) yes C11 C16 1.456(6) yes C11 C21 1.464(6) no C14 C15 1.455(6) yes C14 C31 1.466(6) no C15 C16 1.559(6) yes C21 C22 1.401(6) no C21 C26 1.399(6) no C22 C23 1.386(6) no C23 C24 1.393(6) no C24 C25 1.406(6) no C24 C27 1.500(6) no C25 C26 1.393(6) no C31 C32 1.400(6) no C31 C36 1.393(6) no C32 C33 1.376(6) no C33 C34 1.395(6) no C34 C35 1.400(6) no C34 C37 1.515(6) no C35 C36 1.380(6) no C7 H7A 0.960(12) no C7 H7B 0.960(2) no C7 H7C 0.960(14) no C8 H8A 0.959(12) no C8 H8B 0.960(9) no C8 H8C 0.960(14) no C15 H15 0.92(3) no C16 H16 0.96(3) no C22 H22 1.12(3) no C23 H23 1.09(3) no C25 H25 0.93(4) no C26 H26 1.08(3) no C27 H27A 0.961(9) no C27 H27B 0.963(2) no C27 H27C 0.96(2) no C32 H32 1.16(3) no C33 H33 0.98(3) no C35 H35 0.94(3) no C36 H36 1.11(3) no C37 H37A 0.961(2) no C37 H37B 0.96(2) no C37 H37C 0.96(2) no loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_publ_flag C11 N12 N13 C1 -173.2(3) no C11 N12 N13 C14 9.2(5) no N13 N12 C11 C21 -166.1(3) no N13 N12 C11 C16 11.8(6) no N12 N13 C1 C4 -19.8(5) no C14 N13 C1 C4 157.7(4) no C14 N13 C1 C2 -24.8(6) no C1 N13 C14 C31 -18.6(6) no N12 N13 C14 C15 -23.6(6) no N12 N13 C14 C31 158.6(4) no N12 N13 C1 C2 157.6(4) no C1 N13 C14 C15 159.2(4) no C8 C6 C15 C14 -8.5(6) no C7 C6 C15 C14 -149.4(4) no C7 C6 C15 C16 107.7(4) no C15 C6 C16 C11 -100.8(4) no C8 C6 C15 C16 -111.4(4) no C16 C6 C15 C14 102.9(4) no C8 C6 C16 C11 10.4(6) no C7 C6 C16 C11 155.3(4) no C7 C6 C16 C15 -103.9(4) no C8 C6 C16 C15 111.2(4) no N12 C11 C16 C6 51.5(6) no N12 C11 C21 C26 25.6(6) no C16 C11 C21 C22 25.8(6) no C16 C11 C21 C26 -152.3(4) no N12 C11 C16 C15 -15.7(6) no C21 C11 C16 C6 -130.7(4) no C21 C11 C16 C15 162.0(4) no N12 C11 C21 C22 -156.2(4) no N13 C14 C15 C6 -51.0(6) no N13 C14 C15 C16 16.9(6) no C31 C14 C15 C6 126.8(4) no C31 C14 C15 C16 -165.2(4) no N13 C14 C31 C32 -50.0(6) no N13 C14 C31 C36 132.5(4) no C15 C14 C31 C32 132.2(4) no C15 C14 C31 C36 -45.3(6) no C6 C15 C16 C11 113.5(4) no C14 C15 C16 C6 -112.4(4) no C14 C15 C16 C11 1.1(5) no C11 C21 C22 C23 178.6(4) no C26 C21 C22 C23 -3.3(6) no C11 C21 C26 C25 179.5(4) no C22 C21 C26 C25 1.3(6) no C21 C22 C23 C24 2.8(6) no C22 C23 C24 C25 -0.4(6) no C22 C23 C24 C27 -179.2(4) no C23 C24 C25 C26 -1.6(6) no C27 C24 C25 C26 177.3(4) no C24 C25 C26 C21 1.1(7) no C14 C31 C32 C33 -176.8(4) no C36 C31 C32 C33 0.6(6) no C14 C31 C36 C35 179.8(3) no C32 C31 C36 C35 2.2(6) no C31 C32 C33 C34 -3.4(6) no C32 C33 C34 C35 3.2(6) no C32 C33 C34 C37 -176.1(4) no C33 C34 C35 C36 -0.2(6) no C37 C34 C35 C36 179.1(4) no C34 C35 C36 C31 -2.4(6) no