data_8101650 _journal_name_full 'Zeitschrift fur Kristallographie - NCS' _journal_year 1998 _publ_section_title ; The Crystal Structures of the N-Methyl-N-phenyl-(2-methyl- 3-phenylcyclopropenyliden)ammoniumperchlorat 1, C~17~H~16~N^+^ClO~4~^-^, and the 3-Cyano-1,2,3-triphenyl- cycloprop-1-ene 2, C~22~H~15~N ; loop_ _publ_author_name 'Irngartinger, Hermann' ' Altreuther, Annegret' ' Krebs, A.' ' Toda, Fumio' _chemical_formula_sum 'C34 H27 N1' _chemical_formula_structural 'C~22~H~15~N x 2 C~6~H~6~' _chemical_formula_weight 449.6 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _cell_length_a 9.666(1) _cell_length_b 28.842(4) _cell_length_c 9.967(1) _cell_angle_alpha 90.0 _cell_angle_beta 107.83(1) _cell_angle_gamma 90.0 _cell_volume 2645(1) _cell_formula_units_z 4 _exptl_crystal_density_diffrn 1.13 _cell_measurement_temperature 218 _diffrn_ambient_temperature 218 _refine_ls_R_factor_obs 0.049 _refine_ls_wR_factor_obs 0.057 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag N1 0.7820(3) 0.11003(9) 0.7868(2) 0.0655(8) Uani ? C1 0.9189(2) 0.13034(8) 0.5043(2) 0.0362(7) Uani ? C2 0.9516(2) 0.16978(8) 0.5692(2) 0.0379(7) Uani ? C3 0.9776(3) 0.12681(8) 0.6636(2) 0.0369(7) Uani ? C4 0.8699(3) 0.11747(9) 0.7354(2) 0.0450(8) Uani ? C5 0.8722(2) 0.10058(8) 0.3829(2) 0.0348(7) Uani ? C6 0.8717(3) 0.05233(9) 0.3990(2) 0.0419(7) Uani ? C7 0.8301(3) 0.02399(9) 0.2827(3) 0.0491(8) Uani ? C8 0.7874(3) 0.0429(1) 0.1495(3) 0.0525(8) Uani ? C9 0.7856(3) 0.0901(1) 0.1315(2) 0.0495(8) Uani ? C10 0.8271(3) 0.11910(9) 0.2476(2) 0.0407(7) Uani ? C11 0.9706(2) 0.21975(8) 0.5807(2) 0.0344(7) Uani ? C12 0.9273(3) 0.24750(9) 0.4611(2) 0.0422(7) Uani ? C13 0.9412(3) 0.29502(9) 0.4743(3) 0.0497(8) Uani ? C14 0.9994(3) 0.31479(9) 0.6055(3) 0.0478(8) Uani ? C15 1.0438(3) 0.28730(9) 0.7239(3) 0.0479(8) Uani ? C16 1.0299(3) 0.23984(9) 0.7120(2) 0.0422(7) Uani ? C17 1.1283(3) 0.10916(8) 0.7344(2) 0.0368(7) Uani ? C18 1.2278(3) 0.10627(9) 0.6591(3) 0.0440(8) Uani ? C19 1.3664(3) 0.0897(1) 0.7207(3) 0.0538(9) Uani ? C20 1.4092(3) 0.07595(9) 0.8607(3) 0.0558(9) Uani ? C21 1.3131(3) 0.07849(9) 0.9369(3) 0.0539(9) Uani ? C22 1.1740(3) 0.09481(9) 0.8748(2) 0.0458(8) Uani ? C30 0.2141(4) 0.0307(2) 0.2544(4) 0.096(1) Uani ? C31 0.2030(3) 0.0777(1) 0.2671(3) 0.097(1) Uani ? C32 0.3296(4) 0.1042(1) 0.3189(3) 0.089(1) Uani ? C33 0.4624(3) 0.0809(1) 0.3561(3) 0.084(1) Uani ? C34 0.4639(3) 0.0346(1) 0.3407(4) 0.082(1) Uani ? C35 0.3419(4) 0.0105(1) 0.2913(4) 0.088(1) Uani ? C40 0.6088(4) 0.2295(1) 0.6451(3) 0.082(1) Uani ? C41 0.4816(4) 0.2075(1) 0.6077(4) 0.097(1) Uani ? C42 0.3582(3) 0.2310(1) 0.5476(4) 0.105(1) Uani ? C43 0.3611(4) 0.2765(1) 0.5232(3) 0.094(1) Uani ? C44 0.4906(4) 0.2986(1) 0.5595(3) 0.083(1) Uani ? C45 0.6156(3) 0.2744(1) 0.6215(3) 0.078(1) Uani ? H6 0.9012 0.0387 0.4937 0.0461 Uiso calc H7 0.8309 -0.0097 0.2947 0.0540 Uiso calc H8 0.7580 0.0225 0.0670 0.0577 Uiso calc H9 0.7548 0.1033 0.0363 0.0545 Uiso calc H10 0.8248 0.1528 0.2344 0.0448 Uiso calc H12 0.8870 0.2334 0.3678 0.0464 Uiso calc H13 0.9097 0.3147 0.3903 0.0547 Uiso calc H14 1.0091 0.3486 0.6145 0.0526 Uiso calc H15 1.0855 0.3015 0.8168 0.0527 Uiso calc H16 1.0618 0.2203 0.7964 0.0465 Uiso calc H18 1.1986 0.1162 0.5604 0.0484 Uiso calc H19 1.4345 0.0875 0.6657 0.0592 Uiso calc H20 1.5081 0.0645 0.9052 0.0614 Uiso calc H21 1.3433 0.0687 1.0358 0.0592 Uiso calc H22 1.1061 0.0964 0.9303 0.0504 Uiso calc H30 0.1260 0.0120 0.2176 0.1058 Uiso calc H31 0.1074 0.0927 0.2402 0.1068 Uiso calc H32 0.3250 0.1379 0.3285 0.0975 Uiso calc H33 0.5537 0.0981 0.3931 0.0920 Uiso calc H34 0.5572 0.0183 0.3666 0.0904 Uiso calc H35 0.3473 -0.0232 0.2821 0.0967 Uiso calc H40 0.6982 0.2122 0.6904 0.0902 Uiso calc H41 0.4780 0.1741 0.6241 0.1064 Uiso calc H42 0.2650 0.2146 0.5214 0.1158 Uiso calc H43 0.2708 0.2935 0.4796 0.1036 Uiso calc H44 0.4949 0.3319 0.5415 0.0910 Uiso calc H45 0.7098 0.2903 0.6483 0.0861 Uiso calc 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 N1 0.069(1) 0.076(2) 0.057(1) -0.004(1) 0.0278(9) 0.005(1) C1 0.037(1) 0.036(1) 0.035(1) 0.004(1) 0.0097(9) 0.005(1) C2 0.038(1) 0.038(1) 0.037(1) 0.005(1) 0.0103(9) 0.005(1) C3 0.044(1) 0.035(1) 0.032(1) 0.002(1) 0.0126(9) 0.002(1) C4 0.056(1) 0.041(1) 0.038(1) -0.001(1) 0.015(1) -0.001(1) C5 0.031(1) 0.037(1) 0.035(1) 0.001(1) 0.0083(9) -0.000(1) C6 0.044(1) 0.040(1) 0.039(1) -0.002(1) 0.008(1) 0.005(1) C7 0.049(2) 0.035(1) 0.057(2) -0.002(1) 0.007(1) -0.004(1) C8 0.050(2) 0.054(2) 0.047(1) -0.005(1) 0.005(1) -0.015(1) C9 0.051(1) 0.061(2) 0.033(1) -0.002(1) 0.007(1) 0.000(1) C10 0.043(1) 0.038(1) 0.040(1) 0.003(1) 0.009(1) 0.004(1) C11 0.034(1) 0.030(1) 0.040(1) -0.000(1) 0.0114(9) 0.003(1) C12 0.043(1) 0.042(1) 0.037(1) 0.002(1) 0.007(1) 0.005(1) C13 0.057(2) 0.039(1) 0.050(1) 0.004(1) 0.012(1) 0.012(1) C14 0.048(1) 0.030(1) 0.065(2) -0.002(1) 0.015(1) 0.001(1) C15 0.048(1) 0.047(2) 0.045(1) -0.004(1) 0.009(1) -0.007(1) C16 0.049(1) 0.039(1) 0.037(1) 0.002(1) 0.010(1) 0.003(1) C17 0.047(1) 0.028(1) 0.034(1) -0.002(1) 0.009(1) -0.001(1) C18 0.045(1) 0.043(1) 0.042(1) 0.002(1) 0.010(1) 0.007(1) C19 0.048(1) 0.050(2) 0.062(2) -0.001(1) 0.015(1) 0.004(1) C20 0.048(2) 0.042(2) 0.063(2) 0.001(1) -0.005(1) -0.003(1) C21 0.067(2) 0.042(1) 0.038(1) 0.004(1) -0.006(1) -0.000(1) C22 0.061(2) 0.039(1) 0.034(1) -0.001(1) 0.009(1) -0.004(1) C30 0.075(2) 0.127(3) 0.092(2) -0.014(2) 0.035(2) 0.004(2) C31 0.055(2) 0.171(4) 0.074(2) 0.047(2) 0.033(1) 0.028(2) C32 0.139(2) 0.076(2) 0.070(2) 0.024(2) 0.059(1) 0.013(2) C33 0.068(2) 0.115(3) 0.065(2) -0.023(2) 0.017(1) 0.013(2) C34 0.064(2) 0.089(2) 0.096(2) 0.020(2) 0.029(2) 0.039(2) C35 0.082(2) 0.082(2) 0.110(2) -0.000(2) 0.045(2) 0.019(2) C40 0.079(2) 0.096(2) 0.067(2) 0.036(2) 0.016(2) 0.007(2) C41 0.146(2) 0.060(2) 0.112(2) -0.014(2) 0.081(2) -0.003(2) C42 0.066(2) 0.146(3) 0.121(2) -0.048(2) 0.054(1) -0.068(2) C43 0.070(2) 0.147(3) 0.056(2) 0.048(2) 0.005(1) -0.021(2) C44 0.146(3) 0.048(2) 0.072(2) 0.011(2) 0.060(1) 0.002(1) C45 0.059(2) 0.103(2) 0.081(2) -0.025(2) 0.033(1) -0.029(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag N1 C4 1.139(4) ? C1 C2 1.299(3) ? C1 C3 1.517(3) ? C1 C5 1.438(3) ? C2 C3 1.529(3) ? C2 C11 1.453(3) ? C3 C4 1.458(4) ? C3 C17 1.501(3) ? C5 C6 1.401(3) ? C5 C10 1.391(3) ? C6 C7 1.374(4) ? C6 H6 0.9800 ? C7 C8 1.376(4) ? C7 H7 0.9800 ? C8 C9 1.374(4) ? C8 H8 0.9800 ? C9 C10 1.384(3) ? C9 H9 0.9800 ? C10 H10 0.9800 ? C11 C12 1.390(3) ? C11 C16 1.385(3) ? C12 C13 1.379(4) ? C12 H12 0.9800 ? C13 C14 1.379(4) ? C13 H13 0.9800 ? C14 C15 1.377(4) ? C14 H14 0.9800 ? C15 C16 1.377(4) ? C15 H15 0.9800 ? C16 H16 0.9800 ? C17 C18 1.391(4) ? C17 C22 1.395(3) ? C18 C19 1.378(3) ? C18 H18 0.9800 ? C19 C20 1.386(4) ? C19 H19 0.9800 ? C20 C21 1.369(5) ? C20 H20 0.9800 ? C21 C22 1.380(4) ? C21 H21 0.9800 ? C22 H22 0.9800 ? C30 C31 1.368(6) ? C30 C35 1.312(5) ? C30 H30 0.9800 ? C31 C32 1.400(5) ? C31 H31 0.9800 ? C32 C33 1.394(5) ? C32 H32 0.9800 ? C33 C34 1.346(5) ? C33 H33 0.9800 ? C34 C35 1.327(5) ? C34 H34 0.9800 ? C35 H35 0.9800 ? C40 C41 1.330(5) ? C40 C45 1.323(5) ? C40 H40 0.9800 ? C41 C42 1.343(5) ? C41 H41 0.9800 ? C42 C43 1.336(6) ? C42 H42 0.9800 ? C43 C44 1.352(5) ? C43 H43 0.9800 ? C44 C45 1.368(4) ? C44 H44 0.9800 ? C45 H45 0.9800 ?