Supplementary Material (ESI) for Perkin Transactions This journal is © The Royal Society of Chemistry 2002 data_global _database_code_CSD 170858 _audit_creation_method 'maXus' _journal_coden_Cambridge 207 _publ_requested_journal 'Perkin Transactions 1' loop_ _publ_author_name _publ_author_address 'Mohsen A.-M. Gomaa' ; Fuculty of Science, Menia University, Menia, Egypt ; _publ_contact_author_name 'Dr Mohsen A M Gomaa' _publ_contact_author_address ; Chemistry Department Faculty of Science Minia University El-Minia 61519 EGYPT ; _publ_contact_author_email MAGOMAA2000@YAHOO.COM _publ_contact_author_fax ? _publ_contact_author_phone ? _publ_section_title ; Reaction of Diimines and Azines with Diphenylcyclopropenone ; _publ_section_abstract ; We present the crystal and molecular structure of ; _publ_section_comment ; The study of the titled structure was undertaken to establish its three dimensional structure. Geometries are tabulated below. All Diagrams and calculations were performed using maXus (Nonius, Delft & MacScience, Japan). ; _publ_section_references ; Mackay, S., Gilmore, C. J.,Edwards, C., Stewart, N. & Shankland, K. (1999). maXus Computer Program for the Solution and Refinement of Crystal Structures. Nonius, The Netherlands, MacScience, Japan & The University of Glasgow. Johnson, C. K. (1976). ORTEP-II. A Fortran Thermal-Ellipsoid Plot Program. Report ORNL-5138. Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA. Otwinowski, Z. and Minor, W, (1997). In Methods in Enzymology, 276, edited by C.W. Carter, Jr. & R.M. Sweet pp. 307-326, New York:Academic Press. Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Waasmaier, D. & Kirfel, A. (1995). Acta Cryst. A51, 416-431. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H34 N2 O' _chemical_formula_weight 426.58 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 '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' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M 'R-3' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 32.814(2) _cell_length_b 32.814(2) _cell_length_c 12.309(1) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 11478.1(14) _cell_formula_units_Z 18 _cell_measurement_temperature 293 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.43 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.111 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4140 _exptl_absorpt_coefficient_mu 0.067 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6293 _diffrn_reflns_av_R_equivalents 0.0317 _diffrn_reflns_av_sigmaI/netI 0.0690 _diffrn_reflns_limit_h_min -37 _diffrn_reflns_limit_h_max 37 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.24 _diffrn_reflns_theta_max 24.18 _reflns_number_total 4039 _reflns_number_gt 2411 _reflns_threshold_expression >2sigma(I) _diffrn_measurement_device 'KappaCCD' _computing_data_collection 'KappaCCD' _computing_cell_refinement ? _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-90 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0736P)^2^+19.5699P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0007(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 4039 _refine_ls_number_parameters 291 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1350 _refine_ls_R_factor_gt 0.0769 _refine_ls_wR_factor_ref 0.2018 _refine_ls_wR_factor_gt 0.1714 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O O 0.20689(8) 0.15015(7) -0.01467(18) 0.0675(7) Uani 1 1 d . . . N1 N 0.23169(9) 0.08885(9) 0.1842(2) 0.0634(8) Uani 1 1 d . . . N2 N 0.17284(10) 0.06193(9) -0.0811(2) 0.0743(9) Uani 1 1 d . . . H1N H 0.1799 0.0917 -0.0953 0.141(3) Uiso 1 1 d R . . C1 C 0.25064(10) 0.13256(11) 0.2291(3) 0.0585(8) Uani 1 1 d . . . C2 C 0.24432(10) 0.16283(10) 0.1630(3) 0.0583(8) Uani 1 1 d . . . C3 C 0.22037(10) 0.13698(10) 0.0682(3) 0.0569(8) Uani 1 1 d . . . C4 C 0.21198(11) 0.09002(10) 0.0840(3) 0.0582(8) Uani 1 1 d . . . C5 C 0.27705(11) 0.14419(12) 0.3319(3) 0.0622(9) Uani 1 1 d . . . C6 C 0.25587(14) 0.12485(15) 0.4298(3) 0.0879(12) Uani 1 1 d . . . H6A H 0.2226 0.1030 0.4320 0.141(3) Uiso 1 1 d R . . C7 C 0.28237(18) 0.13714(19) 0.5230(3) 0.1128(16) Uani 1 1 d . . . H7A H 0.2680 0.1231 0.5912 0.141(3) Uiso 1 1 d R . . C8 C 0.32970(18) 0.1692(2) 0.5194(4) 0.1211(18) Uani 1 1 d . . . H8A H 0.3482 0.1780 0.5846 0.141(3) Uiso 1 1 d R . . C9 C 0.35054(15) 0.18873(18) 0.4242(4) 0.1111(16) Uani 1 1 d . . . H9A H 0.3835 0.2115 0.4216 0.141(3) Uiso 1 1 d R . . C10 C 0.32460(13) 0.17636(14) 0.3305(3) 0.0825(11) Uani 1 1 d . . . H10A H 0.3393 0.1900 0.2623 0.141(3) Uiso 1 1 d R . . C11 C 0.25629(11) 0.21181(12) 0.1846(3) 0.0707(10) Uani 1 1 d . . . C12 C 0.25187(14) 0.22685(15) 0.2871(4) 0.0966(13) Uani 1 1 d . . . H12A H 0.2429 0.2051 0.3466 0.141(3) Uiso 1 1 d R . . C13 C 0.26014(19) 0.2725(2) 0.3017(5) 0.128(2) Uani 1 1 d . . . H13A H 0.2578 0.2826 0.3735 0.141(3) Uiso 1 1 d R . . C14 C 0.2720(2) 0.3022(2) 0.2170(7) 0.152(3) Uani 1 1 d . . . H14A H 0.2765 0.3332 0.2291 0.141(3) Uiso 1 1 d R . . C15 C 0.27706(18) 0.28852(16) 0.1163(5) 0.130(2) Uani 1 1 d . . . H15A H 0.2860 0.3108 0.0580 0.141(3) Uiso 1 1 d R . . C16 C 0.26958(14) 0.24345(13) 0.0997(4) 0.0939(13) Uani 1 1 d . . . H16A H 0.2738 0.2341 0.0286 0.141(3) Uiso 1 1 d R . . C17 C 0.23312(12) 0.04861(11) 0.2330(3) 0.0743(10) Uani 1 1 d . . . H17A H 0.2517 0.0605 0.2978 0.141(3) Uiso 1 1 d R . . C18 C 0.18469(14) 0.01069(14) 0.2700(4) 0.1002(14) Uani 1 1 d . . . H18A H 0.1642 -0.0022 0.2083 0.141(3) Uiso 1 1 d R . . H18B H 0.1717 0.0243 0.3180 0.141(3) Uiso 1 1 d R . . C19 C 0.1885(2) -0.02751(19) 0.3288(5) 0.149(3) Uani 1 1 d . . . H19A H 0.1579 -0.0525 0.3493 0.141(3) Uiso 1 1 d R . . H19B H 0.2067 -0.0148 0.3937 0.141(3) Uiso 1 1 d R . . C20 C 0.2129(3) -0.04641(18) 0.2616(6) 0.172(3) Uani 1 1 d . . . H20A H 0.2152 -0.0706 0.2999 0.141(3) Uiso 1 1 d R . . H20B H 0.1938 -0.0604 0.1983 0.141(3) Uiso 1 1 d R . . C21 C 0.2611(2) -0.00874(17) 0.2257(5) 0.129(2) Uani 1 1 d . . . H21A H 0.2810 0.0042 0.2882 0.141(3) Uiso 1 1 d R . . H21B H 0.2748 -0.0221 0.1788 0.141(3) Uiso 1 1 d R . . C22 C 0.25842(16) 0.03063(15) 0.1648(4) 0.1002(14) Uani 1 1 d . . . H22A H 0.2893 0.0559 0.1472 0.141(3) Uiso 1 1 d R . . H22B H 0.2413 0.0184 0.0983 0.141(3) Uiso 1 1 d R . . C23 C 0.18840(11) 0.05407(11) 0.0112(3) 0.0657(9) Uani 1 1 d . . . H23A H 0.1831 0.0231 0.0271 0.141(3) Uiso 1 1 d R . . C24 C 0.14530(13) 0.02607(12) -0.1613(3) 0.0784(11) Uani 1 1 d . . . H24A H 0.1519 0.0009 -0.1530 0.141(3) Uiso 1 1 d R . . C25 C 0.09442(16) 0.0068(2) -0.1449(4) 0.1349(19) Uani 1 1 d . . . H25A H 0.0857 -0.0080 -0.0749 0.141(3) Uiso 1 1 d R . . H25B H 0.0877 0.0321 -0.1465 0.141(3) Uiso 1 1 d R . . C26 C 0.0656(2) -0.0292(3) -0.2317(6) 0.180(3) Uani 1 1 d . . . H26A H 0.0326 -0.0405 -0.2219 0.141(3) Uiso 1 1 d R . . H26B H 0.0706 -0.0555 -0.2259 0.141(3) Uiso 1 1 d R . . C27 C 0.0782(3) -0.0091(3) -0.3402(6) 0.184(4) Uani 1 1 d . . . H27A H 0.0723 0.0166 -0.3471 0.141(3) Uiso 1 1 d R . . H27B H 0.0602 -0.0321 -0.3947 0.141(3) Uiso 1 1 d R . . C28 C 0.1297(3) 0.0097(3) -0.3584(5) 0.175(3) Uani 1 1 d . . . H28A H 0.1356 -0.0161 -0.3546 0.141(3) Uiso 1 1 d R . . H28B H 0.1390 0.0238 -0.4291 0.141(3) Uiso 1 1 d R . . C29 C 0.1597(2) 0.04539(19) -0.2726(4) 0.1323(19) Uani 1 1 d . . . H29A H 0.1552 0.0720 -0.2797 0.141(3) Uiso 1 1 d R . . H29B H 0.1926 0.0562 -0.2826 0.141(3) Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O 0.0772(15) 0.0617(13) 0.0741(15) -0.0021(11) -0.0154(12) 0.0427(12) N1 0.0735(18) 0.0545(17) 0.0636(17) -0.0006(13) -0.0138(14) 0.0330(14) N2 0.089(2) 0.0597(17) 0.078(2) -0.0132(15) -0.0286(16) 0.0399(16) C1 0.0543(18) 0.057(2) 0.063(2) -0.0064(16) -0.0047(15) 0.0271(16) C2 0.0537(18) 0.0520(19) 0.071(2) -0.0097(17) -0.0074(16) 0.0275(15) C3 0.0554(18) 0.0548(19) 0.067(2) -0.0019(16) -0.0032(16) 0.0324(16) C4 0.0629(19) 0.0512(19) 0.062(2) -0.0071(16) -0.0111(16) 0.0297(16) C5 0.063(2) 0.072(2) 0.056(2) -0.0067(17) -0.0022(17) 0.0378(19) C6 0.076(2) 0.114(3) 0.068(3) -0.006(2) 0.001(2) 0.043(2) C7 0.109(4) 0.170(5) 0.056(3) -0.008(3) 0.002(2) 0.067(4) C8 0.095(4) 0.203(6) 0.066(3) -0.024(3) -0.017(3) 0.075(4) C9 0.071(3) 0.171(5) 0.079(3) -0.029(3) -0.012(2) 0.051(3) C10 0.071(3) 0.109(3) 0.063(2) -0.014(2) -0.0055(19) 0.041(2) C11 0.058(2) 0.061(2) 0.097(3) -0.021(2) -0.0230(19) 0.0332(17) C12 0.094(3) 0.089(3) 0.116(3) -0.039(3) -0.023(2) 0.053(2) C13 0.130(4) 0.111(4) 0.167(6) -0.081(4) -0.056(4) 0.077(4) C14 0.164(5) 0.084(4) 0.232(8) -0.075(5) -0.101(6) 0.080(4) C15 0.149(5) 0.061(3) 0.179(6) -0.023(3) -0.074(4) 0.051(3) C16 0.101(3) 0.055(2) 0.124(4) -0.006(2) -0.032(3) 0.037(2) C17 0.082(2) 0.062(2) 0.081(2) 0.0095(18) -0.0114(19) 0.037(2) C18 0.086(3) 0.083(3) 0.111(3) 0.033(2) -0.013(2) 0.027(2) C19 0.132(5) 0.093(4) 0.173(6) 0.062(4) -0.035(4) 0.020(3) C20 0.175(6) 0.068(3) 0.250(9) 0.022(4) -0.107(6) 0.044(4) C21 0.147(5) 0.090(3) 0.179(5) -0.004(3) -0.057(4) 0.080(4) C22 0.117(3) 0.089(3) 0.113(3) -0.008(2) -0.027(3) 0.066(3) C23 0.070(2) 0.058(2) 0.073(2) -0.0007(17) -0.0126(18) 0.0340(17) C24 0.090(3) 0.064(2) 0.086(3) -0.016(2) -0.028(2) 0.041(2) C25 0.094(4) 0.152(5) 0.123(4) -0.032(4) -0.028(3) 0.034(3) C26 0.124(5) 0.165(6) 0.205(7) -0.056(6) -0.084(5) 0.038(4) C27 0.245(9) 0.167(6) 0.169(7) -0.077(5) -0.147(7) 0.124(7) C28 0.248(8) 0.192(7) 0.097(4) -0.054(4) -0.054(5) 0.118(7) C29 0.160(5) 0.137(4) 0.083(3) -0.024(3) -0.011(3) 0.062(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O C3 1.270(3) . ? N1 C1 1.363(4) . ? N1 C4 1.402(4) . ? N1 C17 1.473(4) . ? N2 C23 1.323(4) . ? N2 C24 1.454(4) . ? C1 C2 1.377(4) . ? C1 C5 1.473(4) . ? C2 C3 1.426(4) . ? C2 C11 1.475(4) . ? C3 C4 1.437(4) . ? C4 C23 1.371(4) . ? C5 C6 1.377(5) . ? C5 C10 1.379(5) . ? C6 C7 1.372(5) . ? C7 C8 1.374(6) . ? C8 C9 1.347(6) . ? C9 C10 1.368(5) . ? C11 C16 1.380(5) . ? C11 C12 1.389(5) . ? C12 C13 1.393(6) . ? C13 C14 1.347(8) . ? C14 C15 1.356(8) . ? C15 C16 1.388(6) . ? C17 C22 1.494(5) . ? C17 C18 1.518(5) . ? C18 C19 1.506(6) . ? C19 C20 1.484(9) . ? C20 C21 1.508(8) . ? C21 C22 1.534(5) . ? C24 C25 1.474(6) . ? C24 C29 1.483(6) . ? C25 C26 1.521(7) . ? C26 C27 1.455(9) . ? C27 C28 1.495(9) . ? C28 C29 1.519(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C4 107.6(2) . . ? C1 N1 C17 125.2(3) . . ? C4 N1 C17 127.3(3) . . ? C23 N2 C24 124.8(3) . . ? N1 C1 C2 111.4(3) . . ? N1 C1 C5 121.4(3) . . ? C2 C1 C5 127.0(3) . . ? C1 C2 C3 107.0(3) . . ? C1 C2 C11 128.7(3) . . ? C3 C2 C11 124.3(3) . . ? O C3 C2 129.6(3) . . ? O C3 C4 124.1(3) . . ? C2 C3 C4 106.3(3) . . ? C23 C4 N1 128.4(3) . . ? C23 C4 C3 123.9(3) . . ? N1 C4 C3 107.8(3) . . ? C6 C5 C10 118.7(3) . . ? C6 C5 C1 122.5(3) . . ? C10 C5 C1 118.8(3) . . ? C7 C6 C5 119.7(4) . . ? C6 C7 C8 120.4(4) . . ? C9 C8 C7 120.2(4) . . ? C8 C9 C10 120.0(4) . . ? C9 C10 C5 120.9(4) . . ? C16 C11 C12 118.0(4) . . ? C16 C11 C2 119.7(3) . . ? C12 C11 C2 122.2(4) . . ? C11 C12 C13 120.0(5) . . ? C14 C13 C12 120.7(6) . . ? C13 C14 C15 120.3(5) . . ? C14 C15 C16 120.2(5) . . ? C11 C16 C15 120.7(5) . . ? N1 C17 C22 113.4(3) . . ? N1 C17 C18 111.6(3) . . ? C22 C17 C18 113.9(3) . . ? C19 C18 C17 109.7(4) . . ? C20 C19 C18 111.5(5) . . ? C19 C20 C21 112.6(5) . . ? C20 C21 C22 110.7(4) . . ? C17 C22 C21 109.6(4) . . ? N2 C23 C4 120.0(3) . . ? N2 C24 C25 111.5(3) . . ? N2 C24 C29 110.2(3) . . ? C25 C24 C29 111.2(4) . . ? C24 C25 C26 111.6(5) . . ? C27 C26 C25 111.6(6) . . ? C26 C27 C28 109.4(5) . . ? C27 C28 C29 112.2(5) . . ? C24 C29 C28 111.5(5) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 24.18 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.203 _refine_diff_density_min -0.144 _refine_diff_density_rms 0.033