# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2010 data_global _journal_name_full 'New J.Chem.' _journal_coden_Cambridge 0440 #TrackingRef 'Trzewik_cif.txt' _audit_update_record ; 2010-04-12 # Formatted by publCIF ; _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Bartosz Trzewik' _publ_contact_author_address ; Faculty of Chemistry, Jagiellonian University, ul. Romana Ingardena 3, 30-060 Krak\ow, Poland ; _publ_contact_author_phone '+48 12 662 40 54' _publ_contact_author_fax '+48 12 662 40 54' _publ_contact_author_email trzewik@chemia.uj.edu.pl _publ_section_title ; Mechanisms of reactions conducted on \a-amido-\a-aminonitrones, determined basing on the structures of their crystalline products and DFT calculations ; loop_ _publ_author_name _publ_author_footnote _publ_author_address 'Bartosz Trzewik' ; ? ; ; Faculty of Chemistry, Jagiellonian University, ul. Romana Ingardena 3, 30-060 Krak\ow, Poland ; 'Tomasz Seidler' ; ? ; ; Faculty of Chemistry, Jagiellonian University, ul. Romana Ingardena 3, 30-060 Krak\ow, Poland ; E.Broclawik ; ? ; ; Institute of Catalysis and Surface Chemistry, Polish Academy of Sciences, ul. Niezapominajek 8, 30-239 Krak\ow, Poland ; 'Katarzyna Stadnicka' ; ? ; ; Faculty of Chemistry, Jagiellonian University, ul. Romana Ingardena 3, 30-060 Krak\ow, Poland ; _publ_section_abstract ; Crystal structures of several compounds obtained from recently synthesised \a-amido-\a-aminonitrones were determined by X-ray diffraction. The compounds belonged to three different classes: 1,2,5-oxadiazin-4-ones, amidines, and dibenzo[d,f][1,3]diazepines. In spite of the fact that they were yielded in reactions of various kinds, all the products contained the same amido-amidine moiety. We discovered that some geometrical parameters within the moiety had non-typical values, for example C(sp^2^)--C(sp^2^) single bonds were outstandingly long. Detailed analysis of the products' geometry, aided with DFT calculations for selected structures, allowed us to propose mechanisms of their formation. ; # Attachment 'Trzewik_cif.txt' #============================================================================= data_(6b) #TrackingRef 'Trzewik_cif.txt' _database_code_depnum_ccdc_archive 'CCDC 750328' _audit_creation_method SHELXL-97 #============================================================================= _chemical_name_systematic ; (E)-5-(4-Methylpyridin-2-yl)-2-phenyl-3-(phenylimino)-1,2,5-oxadiazinan-4-one ; _chemical_name_common ;(E)-5-(4-Methylpyridin-2-yl)-2-phenyl-3-(phenylimino)-1,2,5- oxadiazinan-4-one ; _chemical_melting_point '414-416 K' _chemical_formula_moiety 'C21 H18 N4 O2' _chemical_formula_sum 'C21 H18 N4 O2' _chemical_formula_weight 358.39 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 triclinic _symmetry_space_group_name_H-M 'P -1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.3512(3) _cell_length_b 10.5145(3) _cell_length_c 10.8469(4) _cell_angle_alpha 116.607(2) _cell_angle_beta 115.147(2) _cell_angle_gamma 94.549(2) _cell_volume 900.91(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2326 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 39.389 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.321 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9565 _exptl_absorpt_correction_T_max 0.9749 _exptl_absorpt_process_details 'HKL DENZO and Scalepack (Otwinowski & Minor, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f and \o scans to fill Ewald sphere' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5519 _diffrn_reflns_av_R_equivalents 0.0261 _diffrn_reflns_av_sigmaI/netI 0.0453 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.59 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4077 _reflns_number_gt 3031 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL DENZO and Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR-92 (ALTOMARE et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep3 (Farrugia,1997)' _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 'w=1/[\s^2^(Fo^2^)+(0.0609P)^2^+0.2162P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4077 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0705 _refine_ls_R_factor_gt 0.0482 _refine_ls_wR_factor_ref 0.1351 _refine_ls_wR_factor_gt 0.1195 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _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 O1 O 0.38980(13) 0.17071(11) -0.02932(13) 0.0443(3) Uani 1 1 d . . . N2 N 0.30162(16) 0.20689(14) 0.04425(16) 0.0423(3) Uani 1 1 d . . . C3 C 0.29779(16) 0.12475(15) 0.11377(17) 0.0352(3) Uani 1 1 d . . . N3 N 0.27148(16) 0.17404(14) 0.22745(15) 0.0416(3) Uani 1 1 d . . . C4 C 0.31240(18) -0.03111(16) 0.02985(18) 0.0384(3) Uani 1 1 d . . . O4 O 0.33336(15) -0.10304(12) 0.09377(14) 0.0528(3) Uani 1 1 d . . . N5 N 0.29457(15) -0.08180(13) -0.11848(15) 0.0412(3) Uani 1 1 d . . . C6 C 0.3067(2) 0.02594(17) -0.16773(19) 0.0460(4) Uani 1 1 d . . . H6A H 0.3572 -0.0003 -0.2288 0.055 Uiso 1 1 calc R . . H6B H 0.2066 0.0228 -0.2354 0.055 Uiso 1 1 calc R . . C21 C 0.29530(17) 0.35499(16) 0.09364(17) 0.0373(3) Uani 1 1 d . . . C22 C 0.1895(2) 0.39748(19) 0.1343(2) 0.0536(4) Uani 1 1 d . . . H22 H 0.1273 0.3322 0.1382 0.064 Uiso 1 1 calc R . . C23 C 0.1767(2) 0.5379(2) 0.1692(2) 0.0604(5) Uani 1 1 d . . . H23 H 0.1056 0.5665 0.1971 0.072 Uiso 1 1 calc R . . C24 C 0.2664(2) 0.63527(19) 0.1636(2) 0.0593(5) Uani 1 1 d . . . H24 H 0.2566 0.7293 0.1870 0.071 Uiso 1 1 calc R . . C25 C 0.3702(3) 0.5926(2) 0.1233(3) 0.0655(5) Uani 1 1 d . . . H25 H 0.4309 0.6580 0.1182 0.079 Uiso 1 1 calc R . . C26 C 0.3873(2) 0.45368(19) 0.0898(2) 0.0534(4) Uani 1 1 d . . . H26 H 0.4604 0.4271 0.0647 0.064 Uiso 1 1 calc R . . C31 C 0.24635(18) 0.08996(16) 0.29176(18) 0.0380(3) Uani 1 1 d . . . C32 C 0.10568(19) -0.0107(2) 0.2193(2) 0.0495(4) Uani 1 1 d . . . H32 H 0.0273 -0.0293 0.1226 0.059 Uiso 1 1 calc R . . C33 C 0.0803(2) -0.0844(2) 0.2896(2) 0.0536(4) Uani 1 1 d . . . H33 H -0.0148 -0.1530 0.2392 0.064 Uiso 1 1 calc R . . C34 C 0.1944(2) -0.05695(19) 0.4331(2) 0.0522(4) Uani 1 1 d . . . H34 H 0.1773 -0.1069 0.4799 0.063 Uiso 1 1 calc R . . C35 C 0.3337(2) 0.0451(2) 0.5066(2) 0.0613(5) Uani 1 1 d . . . H35 H 0.4118 0.0640 0.6037 0.074 Uiso 1 1 calc R . . C36 C 0.3595(2) 0.1201(2) 0.4381(2) 0.0549(4) Uani 1 1 d . . . H36 H 0.4537 0.1914 0.4908 0.066 Uiso 1 1 calc R . . N51 N 0.33572(19) -0.24448(16) -0.31704(18) 0.0554(4) Uani 1 1 d . . . C52 C 0.27954(18) -0.23327(16) -0.22490(18) 0.0412(4) Uani 1 1 d . . . C53 C 0.2078(2) -0.35577(18) -0.2328(2) 0.0507(4) Uani 1 1 d . . . H53 H 0.1701 -0.3421 -0.1654 0.061 Uiso 1 1 calc R . . C54 C 0.1933(2) -0.49908(19) -0.3428(2) 0.0565(5) Uani 1 1 d . . . C55 C 0.2528(2) -0.5113(2) -0.4383(2) 0.0633(5) Uani 1 1 d . . . H55 H 0.2459 -0.6055 -0.5132 0.076 Uiso 1 1 calc R . . C56 C 0.3220(3) -0.3837(2) -0.4220(2) 0.0659(5) Uani 1 1 d . . . H56 H 0.3616 -0.3941 -0.4872 0.079 Uiso 1 1 calc R . . C57 C 0.1159(3) -0.6361(2) -0.3567(3) 0.0906(8) Uani 1 1 d . . . H57A H 0.0822 -0.6056 -0.2811 0.109 Uiso 0.50 1 calc PR . . H57B H 0.1856 -0.6887 -0.3338 0.109 Uiso 0.50 1 calc PR . . H57C H 0.0304 -0.7016 -0.4640 0.109 Uiso 0.50 1 calc PR . . H57D H 0.1167 -0.7250 -0.4382 0.109 Uiso 0.50 1 calc PR . . H57E H 0.0132 -0.6419 -0.3855 0.109 Uiso 0.50 1 calc PR . . H57F H 0.1684 -0.6290 -0.2553 0.109 Uiso 0.50 1 calc PR . . 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 O1 0.0636(7) 0.0380(6) 0.0556(7) 0.0293(5) 0.0436(6) 0.0245(5) N2 0.0667(9) 0.0355(6) 0.0542(8) 0.0306(6) 0.0449(7) 0.0276(6) C3 0.0446(8) 0.0308(7) 0.0387(7) 0.0221(6) 0.0237(7) 0.0159(6) N3 0.0624(8) 0.0348(6) 0.0442(7) 0.0249(6) 0.0351(7) 0.0223(6) C4 0.0523(9) 0.0328(7) 0.0431(8) 0.0233(7) 0.0306(7) 0.0188(7) O4 0.0917(9) 0.0412(6) 0.0583(7) 0.0363(6) 0.0513(7) 0.0354(6) N5 0.0618(8) 0.0325(6) 0.0420(7) 0.0223(6) 0.0330(7) 0.0215(6) C6 0.0734(11) 0.0398(8) 0.0450(8) 0.0280(7) 0.0388(9) 0.0275(8) C21 0.0495(9) 0.0310(7) 0.0358(7) 0.0210(6) 0.0215(7) 0.0163(6) C22 0.0713(12) 0.0434(9) 0.0745(12) 0.0378(9) 0.0511(10) 0.0282(8) C23 0.0825(13) 0.0515(10) 0.0794(13) 0.0412(10) 0.0567(12) 0.0414(10) C24 0.0917(14) 0.0382(9) 0.0671(12) 0.0332(9) 0.0484(11) 0.0337(9) C25 0.0954(15) 0.0379(9) 0.0891(14) 0.0384(10) 0.0622(13) 0.0246(10) C26 0.0657(11) 0.0402(9) 0.0721(12) 0.0329(9) 0.0454(10) 0.0216(8) C31 0.0568(9) 0.0333(7) 0.0406(8) 0.0231(6) 0.0330(7) 0.0223(7) C32 0.0498(10) 0.0553(10) 0.0490(9) 0.0351(8) 0.0220(8) 0.0172(8) C33 0.0529(10) 0.0559(10) 0.0616(11) 0.0379(9) 0.0307(9) 0.0142(8) C34 0.0757(12) 0.0489(10) 0.0497(9) 0.0329(8) 0.0390(9) 0.0205(9) C35 0.0704(12) 0.0634(11) 0.0433(9) 0.0351(9) 0.0192(9) 0.0091(10) C36 0.0556(11) 0.0554(10) 0.0469(9) 0.0310(8) 0.0195(8) 0.0054(8) N51 0.0796(11) 0.0431(8) 0.0513(8) 0.0210(7) 0.0440(8) 0.0219(7) C52 0.0495(9) 0.0350(8) 0.0384(8) 0.0173(7) 0.0242(7) 0.0173(7) C53 0.0612(11) 0.0380(8) 0.0573(10) 0.0216(8) 0.0379(9) 0.0165(8) C54 0.0603(11) 0.0356(9) 0.0610(11) 0.0180(8) 0.0304(9) 0.0130(8) C55 0.0808(13) 0.0379(9) 0.0578(11) 0.0114(8) 0.0405(11) 0.0213(9) C56 0.0942(15) 0.0501(10) 0.0595(11) 0.0194(9) 0.0544(12) 0.0254(10) C57 0.118(2) 0.0376(11) 0.112(2) 0.0253(12) 0.0729(18) 0.0135(11) _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 O1 C6 1.400(2) . ? O1 N2 1.420(2) . ? N2 C3 1.386(2) . ? N2 C21 1.420(2) . ? C3 N3 1.264(2) . ? C3 C4 1.535(2) . ? N3 C31 1.416(2) . ? C4 O4 1.211(2) . ? C4 N5 1.368(2) . ? N5 C52 1.433(2) . ? N5 C6 1.470(2) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C21 C26 1.379(2) . ? C21 C22 1.380(2) . ? C22 C23 1.383(2) . ? C22 H22 0.9300 . ? C23 C24 1.367(3) . ? C23 H23 0.9300 . ? C24 C25 1.359(3) . ? C24 H24 0.9300 . ? C25 C26 1.385(2) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? C31 C32 1.377(2) . ? C31 C36 1.379(2) . ? C32 C33 1.385(2) . ? C32 H32 0.9300 . ? C33 C34 1.372(2) . ? C33 H33 0.9300 . ? C34 C35 1.370(3) . ? C34 H34 0.9300 . ? C35 C36 1.382(2) . ? C35 H35 0.9300 . ? C36 H36 0.9300 . ? N51 C52 1.323(2) . ? N51 C56 1.340(2) . ? C52 C53 1.383(2) . ? C53 C54 1.385(2) . ? C53 H53 0.9300 . ? C54 C55 1.381(3) . ? C54 C57 1.503(3) . ? C55 C56 1.368(3) . ? C55 H55 0.9300 . ? C56 H56 0.9300 . ? C57 H57A 0.9600 . ? C57 H57B 0.9600 . ? C57 H57C 0.9600 . ? C57 H57D 0.9600 . ? C57 H57E 0.9600 . ? C57 H57F 0.9600 . ? 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 C6 O1 N2 106.6(1) . . ? C3 N2 C21 128.6(1) . . ? C3 N2 O1 111.9(1) . . ? C21 N2 O1 112.7(1) . . ? N3 C3 N2 120.4(1) . . ? N3 C3 C4 125.3(1) . . ? N2 C3 C4 114.0(1) . . ? C3 N3 C31 124.2(1) . . ? O4 C4 N5 124.2(1) . . ? O4 C4 C3 119.6(1) . . ? N5 C4 C3 116.2(1) . . ? C4 N5 C52 123.6(1) . . ? C4 N5 C6 119.4(1) . . ? C52 N5 C6 116.7(1) . . ? O1 C6 N5 108.6(1) . . ? O1 C6 H6A 110.0 . . ? N5 C6 H6A 110.0 . . ? O1 C6 H6B 110.0 . . ? N5 C6 H6B 110.0 . . ? H6A C6 H6B 108.4 . . ? C26 C21 C22 119.5(1) . . ? C26 C21 N2 120.1(1) . . ? C22 C21 N2 120.3(1) . . ? C21 C22 C23 119.5(2) . . ? C21 C22 H22 120.3 . . ? C23 C22 H22 120.3 . . ? C24 C23 C22 121.3(2) . . ? C24 C23 H23 119.4 . . ? C22 C23 H23 119.4 . . ? C25 C24 C23 119.0(2) . . ? C25 C24 H24 120.5 . . ? C23 C24 H24 120.5 . . ? C24 C25 C26 121.2(2) . . ? C24 C25 H25 119.4 . . ? C26 C25 H25 119.4 . . ? C21 C26 C25 119.7(2) . . ? C21 C26 H26 120.2 . . ? C25 C26 H26 120.2 . . ? C32 C31 C36 118.9(1) . . ? C32 C31 N3 121.1(1) . . ? C36 C31 N3 119.7(1) . . ? C31 C32 C33 120.4(2) . . ? C31 C32 H32 119.8 . . ? C33 C32 H32 119.8 . . ? C34 C33 C32 120.5(2) . . ? C34 C33 H33 119.7 . . ? C32 C33 H33 119.7 . . ? C33 C34 C35 119.1(2) . . ? C33 C34 H34 120.4 . . ? C35 C34 H34 120.4 . . ? C34 C35 C36 120.7(2) . . ? C34 C35 H35 119.6 . . ? C36 C35 H35 119.6 . . ? C31 C36 C35 120.4(2) . . ? C31 C36 H36 119.8 . . ? C35 C36 H36 119.8 . . ? C52 N51 C56 116.8(2) . . ? N51 C52 C53 123.8(1) . . ? N51 C52 N5 113.9(1) . . ? C53 C52 N5 122.3(1) . . ? C52 C53 C54 118.8(2) . . ? C52 C53 H53 120.6 . . ? C54 C53 H53 120.6 . . ? C55 C54 C53 117.7(2) . . ? C55 C54 C57 121.4(2) . . ? C53 C54 C57 121.0(2) . . ? C56 C55 C54 119.5(2) . . ? C56 C55 H55 120.3 . . ? C54 C55 H55 120.3 . . ? N51 C56 C55 123.5(2) . . ? N51 C56 H56 118.2 . . ? C55 C56 H56 118.2 . . ? C54 C57 H57A 109.5 . . ? C54 C57 H57B 109.5 . . ? H57A C57 H57B 109.5 . . ? C54 C57 H57C 109.5 . . ? H57A C57 H57C 109.5 . . ? H57B C57 H57C 109.5 . . ? C54 C57 H57D 109.5 . . ? C54 C57 H57E 109.5 . . ? H57D C57 H57E 109.5 . . ? C54 C57 H57F 109.5 . . ? H57D C57 H57F 109.5 . . ? H57E C57 H57F 109.5 . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 O1 N2 C3 71.6(2) . . . . ? C6 O1 N2 C21 -134.7(1) . . . . ? C21 N2 C3 N3 7.5(2) . . . . ? O1 N2 C3 N3 155.9(1) . . . . ? C21 N2 C3 C4 -178.1(1) . . . . ? O1 N2 C3 C4 -29.7(2) . . . . ? N2 C3 N3 C31 171.6(1) . . . . ? C4 C3 N3 C31 -2.2(2) . . . . ? N3 C3 C4 O4 -17.0(2) . . . . ? N2 C3 C4 O4 168.9(2) . . . . ? N3 C3 C4 N5 160.6(2) . . . . ? N2 C3 C4 N5 -13.5(2) . . . . ? O4 C4 N5 C52 8.2(3) . . . . ? C3 C4 N5 C52 -169.3(1) . . . . ? O4 C4 N5 C6 -165.2(2) . . . . ? C3 C4 N5 C6 17.3(2) . . . . ? N2 O1 C6 N5 -65.5(2) . . . . ? C4 N5 C6 O1 22.0(2) . . . . ? C52 N5 C6 O1 -151.9(1) . . . . ? C3 N2 C21 C26 138.8(2) . . . . ? O1 N2 C21 C26 -9.4(2) . . . . ? C3 N2 C21 C22 -46.0(2) . . . . ? O1 N2 C21 C22 165.7(1) . . . . ? C26 C21 C22 C23 0.5(3) . . . . ? N2 C21 C22 C23 -174.7(2) . . . . ? C21 C22 C23 C24 0.3(3) . . . . ? C22 C23 C24 C25 -0.2(3) . . . . ? C23 C24 C25 C26 -0.6(3) . . . . ? C22 C21 C26 C25 -1.3(3) . . . . ? N2 C21 C26 C25 173.8(2) . . . . ? C24 C25 C26 C21 1.4(3) . . . . ? C3 N3 C31 C32 -83.0(2) . . . . ? C3 N3 C31 C36 103.9(2) . . . . ? C36 C31 C32 C33 -2.4(2) . . . . ? N3 C31 C32 C33 -175.5(2) . . . . ? C31 C32 C33 C34 0.7(3) . . . . ? C32 C33 C34 C35 0.4(3) . . . . ? C33 C34 C35 C36 0.3(3) . . . . ? C32 C31 C36 C35 3.0(3) . . . . ? N3 C31 C36 C35 176.3(2) . . . . ? C34 C35 C36 C31 -2.0(3) . . . . ? C56 N51 C52 C53 -0.6(3) . . . . ? C56 N51 C52 N5 -178.5(2) . . . . ? C4 N5 C52 N51 -148.6(2) . . . . ? C6 N5 C52 N51 24.9(2) . . . . ? C4 N5 C52 C53 33.5(2) . . . . ? C6 N5 C52 C53 -153.0(2) . . . . ? N51 C52 C53 C54 0.0(3) . . . . ? N5 C52 C53 C54 177.8(2) . . . . ? C52 C53 C54 C55 0.5(3) . . . . ? C52 C53 C54 C57 -179.8(2) . . . . ? C53 C54 C55 C56 -0.4(3) . . . . ? C57 C54 C55 C56 179.9(2) . . . . ? C52 N51 C56 C55 0.7(3) . . . . ? C54 C55 C56 N51 -0.2(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag C53 H53 O4 0.93 2.46 2.899(2) 109 . Y C6 H6A N51 0.97 2.26 2.687(2) 106 . Y C22 H22 N3 0.93 2.56 2.996(2) 109 . Y _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.180 _refine_diff_density_min -0.181 _refine_diff_density_rms 0.035 #============================================================================= data_(7a) #TrackingRef 'Trzewik_cif.txt' _database_code_depnum_ccdc_archive 'CCDC 750329' _audit_creation_method SHELXL-97 #============================================================================= _chemical_name_systematic ; (Z)-2-(phenylamino)-2-(phenylimino)-N-(pyridin-2-yl)ethanamide ; _chemical_name_common (Z)-2-(phenylamino)-2-(phenylimino)-N-(pyridin-2-yl)ethanamide _chemical_melting_point ? _chemical_formula_moiety 'C19 H16 N4 O' _chemical_formula_sum 'C19 H16 N4 O' _chemical_formula_weight 316.36 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 monoclinic _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 26.1851(8) _cell_length_b 9.1055(3) _cell_length_c 13.7491(6) _cell_angle_alpha 90.00 _cell_angle_beta 98.881(1) _cell_angle_gamma 90.00 _cell_volume 3238.9(2) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2294 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.57 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.298 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1328 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9569 _exptl_absorpt_correction_T_max 0.9967 _exptl_absorpt_process_details 'HKL DENZO and Scalepack (Otwinowski & Minor, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f and \o scans to fill Ewald sphere' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5189 _diffrn_reflns_av_R_equivalents 0.0216 _diffrn_reflns_av_sigmaI/netI 0.0413 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.74 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3630 _reflns_number_gt 2814 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL DENZO and Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR-92 (ALTOMARE et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep3 (Farrugia,1997)' _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. H-atoms attached to two N-atoms (N2 and N5) were located on the Fourier difference maps and were refined using DFIX restraints with the target value of the N-H bond length 0.88 \%A with an assumed estimated standard deviation of 0.01 \%A (according to SHELX97 program instructions). ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0407P)^2^+1.7843P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3630 _refine_ls_number_parameters 223 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0635 _refine_ls_R_factor_gt 0.0451 _refine_ls_wR_factor_ref 0.1145 _refine_ls_wR_factor_gt 0.1039 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0.001 _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 N2 N 0.68726(4) 0.12875(14) 0.11527(9) 0.0394(3) Uani 1 1 d D . . H2 H 0.7171(5) 0.1147(18) 0.1548(11) 0.047 Uiso 1 1 d D . . N3 N 0.65340(4) 0.08460(14) -0.05645(8) 0.0389(3) Uani 1 1 d . . . C3 C 0.68679(5) 0.07794(15) 0.02247(10) 0.0339(3) Uani 1 1 d . . . C4 C 0.73729(5) -0.00114(16) 0.01405(10) 0.0372(3) Uani 1 1 d . . . O4 O 0.77167(4) -0.00910(15) 0.08433(8) 0.0587(3) Uani 1 1 d . . . N5 N 0.73963(4) -0.05573(15) -0.07637(9) 0.0396(3) Uani 1 1 d D . . H5 H 0.7117(5) -0.0431(18) -0.1183(11) 0.048 Uiso 1 1 d D . . C21 C 0.64686(5) 0.19147(16) 0.15931(9) 0.0339(3) Uani 1 1 d . . . C22 C 0.65852(6) 0.31120(17) 0.22126(11) 0.0414(3) Uani 1 1 d . . . H22 H 0.6920 0.3482 0.2327 0.050 Uiso 1 1 calc R . . C23 C 0.62049(6) 0.37517(19) 0.26571(12) 0.0500(4) Uani 1 1 d . . . H23 H 0.6284 0.4549 0.3076 0.060 Uiso 1 1 calc R . . C24 C 0.57066(6) 0.3216(2) 0.24853(13) 0.0548(4) Uani 1 1 d . . . H24 H 0.5449 0.3664 0.2776 0.066 Uiso 1 1 calc R . . C25 C 0.55923(6) 0.20151(19) 0.18813(12) 0.0483(4) Uani 1 1 d . . . H25 H 0.5257 0.1650 0.1768 0.058 Uiso 1 1 calc R . . C26 C 0.59726(5) 0.13487(16) 0.14422(10) 0.0389(3) Uani 1 1 d . . . H26 H 0.5895 0.0524 0.1048 0.047 Uiso 1 1 calc R . . C31 C 0.60768(5) 0.16871(17) -0.06742(10) 0.0379(3) Uani 1 1 d . . . C32 C 0.56156(6) 0.1023(2) -0.10763(12) 0.0522(4) Uani 1 1 d . . . H32 H 0.5613 0.0038 -0.1255 0.063 Uiso 1 1 calc R . . C33 C 0.51608(7) 0.1817(3) -0.12132(15) 0.0664(5) Uani 1 1 d . . . H33 H 0.4852 0.1354 -0.1466 0.080 Uiso 1 1 calc R . . C34 C 0.51601(7) 0.3285(3) -0.09789(15) 0.0676(6) Uani 1 1 d . . . H34 H 0.4853 0.3815 -0.1071 0.081 Uiso 1 1 calc R . . C35 C 0.56175(7) 0.3959(2) -0.06070(14) 0.0581(5) Uani 1 1 d . . . H35 H 0.5619 0.4954 -0.0455 0.070 Uiso 1 1 calc R . . C36 C 0.60758(6) 0.31793(18) -0.04547(12) 0.0458(4) Uani 1 1 d . . . H36 H 0.6383 0.3651 -0.0206 0.055 Uiso 1 1 calc R . . N51 N 0.77398(4) -0.15234(14) -0.20562(8) 0.0392(3) Uani 1 1 d . . . C52 C 0.78095(5) -0.12933(15) -0.10880(10) 0.0336(3) Uani 1 1 d . . . C53 C 0.82500(6) -0.17403(17) -0.04605(11) 0.0415(3) Uani 1 1 d . . . H53 H 0.8286 -0.1572 0.0214 0.050 Uiso 1 1 calc R . . C54 C 0.86312(6) -0.24394(18) -0.08711(12) 0.0487(4) Uani 1 1 d . . . H54 H 0.8932 -0.2750 -0.0473 0.058 Uiso 1 1 calc R . . C55 C 0.85674(6) -0.26792(19) -0.18710(12) 0.0516(4) Uani 1 1 d . . . H55 H 0.8822 -0.3143 -0.2160 0.062 Uiso 1 1 calc R . . C56 C 0.81174(6) -0.22143(18) -0.24266(11) 0.0472(4) Uani 1 1 d . . . H56 H 0.8072 -0.2389 -0.3101 0.057 Uiso 1 1 calc 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 N2 0.0308(6) 0.0565(8) 0.0316(6) -0.0070(5) 0.0070(5) 0.0042(6) N3 0.0339(6) 0.0499(7) 0.0337(6) -0.0021(5) 0.0077(5) 0.0034(5) C3 0.0314(7) 0.0400(7) 0.0320(7) -0.0015(6) 0.0104(5) -0.0025(6) C4 0.0333(7) 0.0467(8) 0.0327(7) -0.0042(6) 0.0084(5) 0.0000(6) O4 0.0419(6) 0.0912(9) 0.0406(6) -0.0194(6) -0.0011(5) 0.0180(6) N5 0.0318(6) 0.0565(8) 0.0310(6) -0.0046(5) 0.0061(5) 0.0073(6) C21 0.0335(7) 0.0419(7) 0.0279(7) 0.0011(5) 0.0095(5) 0.0032(6) C22 0.0361(7) 0.0494(8) 0.0388(8) -0.0065(6) 0.0061(6) -0.0028(7) C23 0.0478(9) 0.0543(10) 0.0486(9) -0.0172(7) 0.0099(7) 0.0018(7) C24 0.0433(9) 0.0687(11) 0.0559(10) -0.0171(9) 0.0186(7) 0.0063(8) C25 0.0368(8) 0.0628(10) 0.0483(9) -0.0081(8) 0.0155(7) -0.0055(7) C26 0.0404(8) 0.0428(8) 0.0354(7) -0.0043(6) 0.0121(6) -0.0048(6) C31 0.0347(7) 0.0509(8) 0.0294(7) 0.0020(6) 0.0096(5) 0.0025(6) C32 0.0422(8) 0.0629(11) 0.0501(10) -0.0075(8) 0.0029(7) -0.0007(8) C33 0.0380(9) 0.0893(15) 0.0694(12) -0.0027(11) -0.0001(8) 0.0033(9) C34 0.0477(10) 0.0841(15) 0.0720(13) 0.0144(11) 0.0122(9) 0.0240(10) C35 0.0638(11) 0.0530(10) 0.0610(11) 0.0137(8) 0.0203(9) 0.0151(9) C36 0.0463(8) 0.0494(9) 0.0435(9) 0.0081(7) 0.0125(7) -0.0007(7) N51 0.0376(6) 0.0495(7) 0.0315(6) -0.0023(5) 0.0089(5) 0.0036(5) C52 0.0320(7) 0.0371(7) 0.0333(7) -0.0018(5) 0.0099(5) -0.0010(6) C53 0.0402(8) 0.0484(8) 0.0355(8) -0.0031(6) 0.0051(6) 0.0047(7) C54 0.0404(8) 0.0541(10) 0.0508(10) -0.0003(7) 0.0049(7) 0.0134(7) C55 0.0487(9) 0.0578(10) 0.0519(10) 0.0007(8) 0.0191(7) 0.0165(8) C56 0.0509(9) 0.0572(10) 0.0360(8) -0.0032(7) 0.0145(7) 0.0104(7) _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 N2 C3 1.356(2) . ? N2 C21 1.418(2) . ? N2 H2 0.89(1) . ? N3 C3 1.286(2) . ? N3 C31 1.410(2) . ? C3 C4 1.526(2) . ? C4 O4 1.217(2) . ? C4 N5 1.349(2) . ? N5 C52 1.403(3) . ? N5 H5 0.87(1) . ? C21 C26 1.383(2) . ? C21 C22 1.388(2) . ? C22 C23 1.376(2) . ? C22 H22 0.9300 . ? C23 C24 1.379(2) . ? C23 H23 0.9300 . ? C24 C25 1.378(2) . ? C24 H24 0.9300 . ? C25 C26 1.382(2) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? C31 C32 1.387(2) . ? C31 C36 1.392(2) . ? C32 C33 1.381(2) . ? C32 H32 0.9300 . ? C33 C34 1.375(3) . ? C33 H33 0.9300 . ? C34 C35 1.372(3) . ? C34 H34 0.9300 . ? C35 C36 1.382(2) . ? C35 H35 0.9300 . ? C36 H36 0.9300 . ? N51 C52 1.332(2) . ? N51 C56 1.337(2) . ? C52 C53 1.390(2) . ? C53 C54 1.376(2) . ? C53 H53 0.9300 . ? C54 C55 1.376(2) . ? C54 H54 0.9300 . ? C55 C56 1.369(2) . ? C55 H55 0.9300 . ? C56 H56 0.9300 . ? 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 C3 N2 C21 129.8(1) . . ? C3 N2 H2 114(1) . . ? C21 N2 H2 116(1) . . ? C3 N3 C31 124.9(1) . . ? N3 C3 N2 133.2(1) . . ? N3 C3 C4 116.3(1) . . ? N2 C3 C4 110.5(1) . . ? O4 C4 N5 125.2(1) . . ? O4 C4 C3 120.8(1) . . ? N5 C4 C3 114.0(1) . . ? C4 N5 C52 128.0(1) . . ? C4 N5 H5 114(1) . . ? C52 N5 H5 118(1) . . ? C26 C21 C22 119.8(1) . . ? C26 C21 N2 122.1(1) . . ? C22 C21 N2 118.1(1) . . ? C23 C22 C21 120.0(1) . . ? C23 C22 H22 120.0 . . ? C21 C22 H22 120.0 . . ? C22 C23 C24 120.3(2) . . ? C22 C23 H23 119.8 . . ? C24 C23 H23 119.8 . . ? C25 C24 C23 119.7(1) . . ? C25 C24 H24 120.1 . . ? C23 C24 H24 120.1 . . ? C24 C25 C26 120.5(1) . . ? C24 C25 H25 119.7 . . ? C26 C25 H25 119.7 . . ? C25 C26 C21 119.6(1) . . ? C25 C26 H26 120.2 . . ? C21 C26 H26 120.2 . . ? C32 C31 C36 118.8(1) . . ? C32 C31 N3 118.6(1) . . ? C36 C31 N3 122.5(1) . . ? C33 C32 C31 120.4(2) . . ? C33 C32 H32 119.8 . . ? C31 C32 H32 119.8 . . ? C34 C33 C32 120.6(2) . . ? C34 C33 H33 119.7 . . ? C32 C33 H33 119.7 . . ? C35 C34 C33 119.3(2) . . ? C35 C34 H34 120.3 . . ? C33 C34 H34 120.3 . . ? C34 C35 C36 120.9(2) . . ? C34 C35 H35 119.5 . . ? C36 C35 H35 119.5 . . ? C35 C36 C31 120.0(2) . . ? C35 C36 H36 120.0 . . ? C31 C36 H36 120.0 . . ? C52 N51 C56 117.4(1) . . ? N51 C52 C53 123.1(1) . . ? N51 C52 N5 113.6(1) . . ? C53 C52 N5 123.3(1) . . ? C54 C53 C52 117.8(1) . . ? C54 C53 H53 121.1 . . ? C52 C53 H53 121.1 . . ? C53 C54 C55 119.9(1) . . ? C53 C54 H54 120.0 . . ? C55 C54 H54 120.0 . . ? C56 C55 C54 118.0(1) . . ? C56 C55 H55 121.0 . . ? C54 C55 H55 121.0 . . ? N51 C56 C55 123.8(2) . . ? N51 C56 H56 118.1 . . ? C55 C56 H56 118.1 . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C31 N3 C3 N2 8.2(3) . . . . ? C31 N3 C3 C4 -171.2(1) . . . . ? C21 N2 C3 N3 9.4(3) . . . . ? C21 N2 C3 C4 -171.2(1) . . . . ? N3 C3 C4 O4 177.9(1) . . . . ? N2 C3 C4 O4 -1.6(2) . . . . ? N3 C3 C4 N5 -0.8(2) . . . . ? N2 C3 C4 N5 179.7(1) . . . . ? O4 C4 N5 C52 -1.0(3) . . . . ? C3 C4 N5 C52 177.7(1) . . . . ? C3 N2 C21 C26 42.4(2) . . . . ? C3 N2 C21 C22 -139.3(2) . . . . ? C26 C21 C22 C23 -1.4(2) . . . . ? N2 C21 C22 C23 -179.8(1) . . . . ? C21 C22 C23 C24 -0.5(3) . . . . ? C22 C23 C24 C25 1.4(3) . . . . ? C23 C24 C25 C26 -0.4(3) . . . . ? C24 C25 C26 C21 -1.5(2) . . . . ? C22 C21 C26 C25 2.4(2) . . . . ? N2 C21 C26 C25 -179.3(1) . . . . ? C3 N3 C31 C32 -131.7(2) . . . . ? C3 N3 C31 C36 52.6(2) . . . . ? C36 C31 C32 C33 -2.9(2) . . . . ? N3 C31 C32 C33 -178.8(2) . . . . ? C31 C32 C33 C34 1.8(3) . . . . ? C32 C33 C34 C35 0.1(3) . . . . ? C33 C34 C35 C36 -0.8(3) . . . . ? C34 C35 C36 C31 -0.4(2) . . . . ? C32 C31 C36 C35 2.2(2) . . . . ? N3 C31 C36 C35 177.9(1) . . . . ? C56 N51 C52 C53 -0.2(2) . . . . ? C56 N51 C52 N5 179.7(1) . . . . ? C4 N5 C52 N51 -171.5(1) . . . . ? C4 N5 C52 C53 8.5(2) . . . . ? N51 C52 C53 C54 0.7(2) . . . . ? N5 C52 C53 C54 -179.3(1) . . . . ? C52 C53 C54 C55 -0.3(2) . . . . ? C53 C54 C55 C56 -0.5(3) . . . . ? C52 N51 C56 C55 -0.6(2) . . . . ? C54 C55 C56 N51 1.0(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag N2 H2 O4 0.89(1) 2.16(2) 2.633(2) 112(1) . Y N2 H2 N51 0.89(1) 2.27(1) 3.089(2) 154(1) 6_556 Y N5 H5 N3 0.87(1) 2.19(2) 2.645(2) 112(1) . Y _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.171 _refine_diff_density_min -0.174 _refine_diff_density_rms 0.032 #============================================================================= data_(7b) #TrackingRef 'Trzewik_cif.txt' _database_code_depnum_ccdc_archive 'CCDC 750330' _audit_creation_method SHELXL-97 #============================================================================= _chemical_name_systematic ; (Z)-N-(4-methylpyridin-2-yl)-2-(phenylamino)-2-(phenylimino)ethanamide ; _chemical_name_common ;(Z)-N-(4-methylpyridin-2-yl)-2-(phenylamino)-2- (phenylimino)ethanamide ; _chemical_melting_point '437-438 K' _chemical_formula_moiety 'C20 H18 N4 O' _chemical_formula_sum 'C20 H18 N4 O' _chemical_formula_weight 330.38 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 monoclinic _symmetry_space_group_name_H-M 'P 21/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.5564(3) _cell_length_b 10.1570(3) _cell_length_c 13.3227(4) _cell_angle_alpha 90.000 _cell_angle_beta 109.473(1) _cell_angle_gamma 90.000 _cell_volume 1729.50(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4904 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.57 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.269 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9566 _exptl_absorpt_correction_T_max 0.9976 _exptl_absorpt_process_details 'HKL DENZO and Scalepack (Otwinowski & Minor, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f and \o scans to fill Ewald sphere' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6633 _diffrn_reflns_av_R_equivalents 0.0298 _diffrn_reflns_av_sigmaI/netI 0.0500 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.56 _diffrn_reflns_theta_max 27.51 _reflns_number_total 3945 _reflns_number_gt 2532 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL DENZO and Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR-92 (ALTOMARE et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep3 (Farrugia,1997)' _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. H-atoms attached to two N-atoms (N2 and N5) were located on the Fourier difference maps and were refined using DFIX restraints with the target value of the N-H bond length 0.88 \%A with an assumed estimated standard deviation of 0.01 \%A (according to SHELX97 program instructions). ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0442P)^2^+0.5708P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0157(19) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3945 _refine_ls_number_parameters 233 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1014 _refine_ls_R_factor_gt 0.0537 _refine_ls_wR_factor_ref 0.1251 _refine_ls_wR_factor_gt 0.1054 _refine_ls_goodness_of_fit_ref 0.990 _refine_ls_restrained_S_all 0.990 _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 N2 N 0.36923(11) 0.10850(17) 0.81441(11) 0.0467(4) Uani 1 1 d D . . H2 H 0.4258(10) 0.1252(19) 0.7982(15) 0.056 Uiso 1 1 d D . . C3 C 0.37110(13) 0.15575(17) 0.90995(13) 0.0397(4) Uani 1 1 d . . . N3 N 0.30915(11) 0.14230(16) 0.96418(11) 0.0460(4) Uani 1 1 d . . . C4 C 0.46783(13) 0.24082(18) 0.95949(13) 0.0429(4) Uani 1 1 d . . . O4 O 0.53270(10) 0.25454(16) 0.91570(10) 0.0645(4) Uani 1 1 d . . . N5 N 0.47356(11) 0.29409(16) 1.05409(11) 0.0446(4) Uani 1 1 d D . . H5 H 0.4207(11) 0.2726(19) 1.0750(14) 0.054 Uiso 1 1 d D . . C21 C 0.28885(13) 0.03531(18) 0.73891(12) 0.0405(4) Uani 1 1 d . . . C22 C 0.31343(15) -0.0838(2) 0.70322(14) 0.0511(5) Uani 1 1 d . . . H22 H 0.3823 -0.1133 0.7258 0.061 Uiso 1 1 calc R . . C23 C 0.23542(17) -0.1587(2) 0.63405(16) 0.0616(6) Uani 1 1 d . . . H23 H 0.2517 -0.2389 0.6097 0.074 Uiso 1 1 calc R . . C24 C 0.13380(17) -0.1155(2) 0.60088(15) 0.0642(6) Uani 1 1 d . . . H24 H 0.0811 -0.1679 0.5561 0.077 Uiso 1 1 calc R . . C25 C 0.10963(15) 0.0049(2) 0.63353(15) 0.0587(6) Uani 1 1 d . . . H25 H 0.0408 0.0346 0.6098 0.070 Uiso 1 1 calc R . . C26 C 0.18757(14) 0.0818(2) 0.70159(13) 0.0473(5) Uani 1 1 d . . . H26 H 0.1718 0.1644 0.7221 0.057 Uiso 1 1 calc R . . C31 C 0.22231(14) 0.0561(2) 0.93528(13) 0.0450(5) Uani 1 1 d . . . C32 C 0.12448(15) 0.1059(2) 0.92653(16) 0.0577(5) Uani 1 1 d . . . H32 H 0.1173 0.1942 0.9413 0.069 Uiso 1 1 calc R . . C33 C 0.03791(16) 0.0250(3) 0.89606(18) 0.0694(7) Uani 1 1 d . . . H33 H -0.0277 0.0597 0.8882 0.083 Uiso 1 1 calc R . . C34 C 0.04789(18) -0.1057(3) 0.87733(18) 0.0728(7) Uani 1 1 d . . . H34 H -0.0109 -0.1596 0.8555 0.087 Uiso 1 1 calc R . . C35 C 0.14507(18) -0.1573(2) 0.89082(16) 0.0662(6) Uani 1 1 d . . . H35 H 0.1522 -0.2468 0.8800 0.079 Uiso 1 1 calc R . . C36 C 0.23243(16) -0.0771(2) 0.92031(14) 0.0531(5) Uani 1 1 d . . . H36 H 0.2981 -0.1128 0.9301 0.064 Uiso 1 1 calc R . . N51 N 0.53668(11) 0.40649(16) 1.21110(11) 0.0477(4) Uani 1 1 d . . . C52 C 0.55199(13) 0.37591(17) 1.11998(13) 0.0391(4) Uani 1 1 d . . . C53 C 0.63633(13) 0.41969(18) 1.09329(14) 0.0437(4) Uani 1 1 d . . . H53 H 0.6430 0.3968 1.0283 0.052 Uiso 1 1 calc R . . C54 C 0.71108(13) 0.49824(18) 1.16444(14) 0.0459(4) Uani 1 1 d . . . C55 C 0.69626(15) 0.5294(2) 1.25939(15) 0.0543(5) Uani 1 1 d . . . H55 H 0.7447 0.5814 1.3096 0.065 Uiso 1 1 calc R . . C56 C 0.60945(16) 0.4828(2) 1.27859(15) 0.0575(5) Uani 1 1 d . . . H56 H 0.6005 0.5056 1.3426 0.069 Uiso 1 1 calc R . . C57 C 0.80371(16) 0.5463(2) 1.13739(19) 0.0648(6) Uani 1 1 d . . . H57A H 0.7996 0.5141 1.0684 0.078 Uiso 0.50 1 calc PR . . H57B H 0.8669 0.5149 1.1896 0.078 Uiso 0.50 1 calc PR . . H57C H 0.8040 0.6408 1.1369 0.078 Uiso 0.50 1 calc PR . . H57D H 0.8474 0.5991 1.1949 0.078 Uiso 0.50 1 calc PR . . H57E H 0.7801 0.5984 1.0736 0.078 Uiso 0.50 1 calc PR . . H57F H 0.8430 0.4724 1.1263 0.078 Uiso 0.50 1 calc PR . . 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 N2 0.0399(8) 0.0600(10) 0.0409(8) -0.0096(7) 0.0144(7) -0.0085(7) C3 0.0378(9) 0.0434(10) 0.0354(9) -0.0011(8) 0.0085(7) -0.0001(8) N3 0.0411(8) 0.0556(10) 0.0419(8) -0.0026(7) 0.0145(7) -0.0078(7) C4 0.0376(9) 0.0506(11) 0.0392(9) -0.0022(8) 0.0111(7) -0.0032(8) O4 0.0510(8) 0.0922(12) 0.0584(8) -0.0271(8) 0.0291(7) -0.0243(8) N5 0.0398(8) 0.0573(10) 0.0379(8) -0.0074(7) 0.0145(6) -0.0111(7) C21 0.0411(9) 0.0471(11) 0.0321(8) -0.0017(8) 0.0106(7) -0.0035(8) C22 0.0490(11) 0.0560(12) 0.0459(10) -0.0070(9) 0.0128(9) 0.0042(9) C23 0.0732(15) 0.0547(13) 0.0541(12) -0.0147(10) 0.0175(11) -0.0012(11) C24 0.0622(13) 0.0770(16) 0.0459(11) -0.0164(11) 0.0080(10) -0.0175(12) C25 0.0446(10) 0.0804(16) 0.0433(10) -0.0019(11) 0.0041(8) 0.0013(11) C26 0.0488(11) 0.0507(12) 0.0394(9) -0.0001(8) 0.0106(8) 0.0045(9) C31 0.0461(10) 0.0558(12) 0.0331(8) 0.0035(8) 0.0132(8) -0.0088(9) C32 0.0502(11) 0.0685(14) 0.0604(12) -0.0027(11) 0.0264(10) -0.0073(10) C33 0.0487(12) 0.0899(19) 0.0732(15) 0.0033(13) 0.0250(11) -0.0132(12) C34 0.0625(15) 0.0816(18) 0.0663(14) 0.0100(13) 0.0106(11) -0.0309(13) C35 0.0763(15) 0.0534(13) 0.0595(13) 0.0113(10) 0.0101(12) -0.0151(12) C36 0.0519(11) 0.0557(13) 0.0457(10) 0.0109(9) 0.0085(9) -0.0027(10) N51 0.0481(9) 0.0582(10) 0.0369(8) -0.0045(7) 0.0142(7) -0.0053(8) C52 0.0389(9) 0.0409(10) 0.0344(8) 0.0002(8) 0.0081(7) 0.0007(8) C53 0.0432(10) 0.0476(11) 0.0414(9) -0.0040(8) 0.0155(8) -0.0039(8) C54 0.0412(9) 0.0416(11) 0.0517(11) 0.0002(9) 0.0113(8) -0.0005(8) C55 0.0509(11) 0.0562(12) 0.0487(11) -0.0114(9) 0.0071(9) -0.0115(10) C56 0.0624(12) 0.0692(14) 0.0387(10) -0.0130(10) 0.0141(9) -0.0078(11) C57 0.0539(12) 0.0593(13) 0.0831(15) -0.0141(12) 0.0253(11) -0.0151(10) _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 N2 C3 1.353(2) . ? N2 C21 1.422(2) . ? N2 H2 0.88(1) . ? C3 N3 1.285(2) . ? C3 C4 1.525(2) . ? N3 C31 1.414(2) . ? C4 O4 1.215(2) . ? C4 N5 1.350(2) . ? N5 C52 1.403(2) . ? N5 H5 0.88(1) . ? C21 C26 1.378(2) . ? C21 C22 1.381(3) . ? C22 C23 1.377(3) . ? C22 H22 0.9300 . ? C23 C24 1.371(3) . ? C23 H23 0.9300 . ? C24 C25 1.374(3) . ? C24 H24 0.9300 . ? C25 C26 1.382(3) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? C31 C36 1.380(3) . ? C31 C32 1.388(3) . ? C32 C33 1.378(3) . ? C32 H32 0.9300 . ? C33 C34 1.367(3) . ? C33 H33 0.9300 . ? C34 C35 1.373(3) . ? C34 H34 0.9300 . ? C35 C36 1.382(3) . ? C35 H35 0.9300 . ? C36 H36 0.9300 . ? N51 C52 1.335(2) . ? N51 C56 1.338(2) . ? C52 C53 1.379(2) . ? C53 C54 1.386(2) . ? C53 H53 0.9300 . ? C54 C55 1.382(3) . ? C54 C57 1.499(3) . ? C55 C56 1.370(3) . ? C55 H55 0.9300 . ? C56 H56 0.9300 . ? C57 H57A 0.9600 . ? C57 H57B 0.9600 . ? C57 H57C 0.9600 . ? C57 H57D 0.9600 . ? C57 H57E 0.9600 . ? C57 H57F 0.9600 . ? 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 C3 N2 C21 128.4(2) . . ? C3 N2 H2 115(1) . . ? C21 N2 H2 117(1) . . ? N3 C3 N2 132.9(2) . . ? N3 C3 C4 116.5(2) . . ? N2 C3 C4 110.6(2) . . ? C3 N3 C31 123.6(2) . . ? O4 C4 N5 125.2(2) . . ? O4 C4 C3 120.9(2) . . ? N5 C4 C3 113.9(2) . . ? C4 N5 C52 128.1(2) . . ? C4 N5 H5 113(1) . . ? C52 N5 H5 119(1) . . ? C26 C21 C22 120.1(2) . . ? C26 C21 N2 120.8(2) . . ? C22 C21 N2 119.1(2) . . ? C23 C22 C21 119.7(2) . . ? C23 C22 H22 120.2 . . ? C21 C22 H22 120.2 . . ? C24 C23 C22 120.3(2) . . ? C24 C23 H23 119.9 . . ? C22 C23 H23 119.9 . . ? C23 C24 C25 120.2(2) . . ? C23 C24 H24 119.9 . . ? C25 C24 H24 119.9 . . ? C24 C25 C26 120.0(2) . . ? C24 C25 H25 120.0 . . ? C26 C25 H25 120.0 . . ? C21 C26 C25 119.7(2) . . ? C21 C26 H26 120.2 . . ? C25 C26 H26 120.2 . . ? C36 C31 C32 118.9(2) . . ? C36 C31 N3 122.2(2) . . ? C32 C31 N3 118.8(2) . . ? C33 C32 C31 120.2(2) . . ? C33 C32 H32 119.9 . . ? C31 C32 H32 119.9 . . ? C34 C33 C32 120.5(2) . . ? C34 C33 H33 119.8 . . ? C32 C33 H33 119.8 . . ? C33 C34 C35 119.7(2) . . ? C33 C34 H34 120.1 . . ? C35 C34 H34 120.1 . . ? C34 C35 C36 120.4(2) . . ? C34 C35 H35 119.8 . . ? C36 C35 H35 119.8 . . ? C31 C36 C35 120.1(2) . . ? C31 C36 H36 119.9 . . ? C35 C36 H36 119.9 . . ? C52 N51 C56 116.3(2) . . ? N51 C52 C53 123.6(2) . . ? N51 C52 N5 113.1(2) . . ? C53 C52 N5 123.4(2) . . ? C52 C53 C54 119.3(2) . . ? C52 C53 H53 120.4 . . ? C54 C53 H53 120.4 . . ? C55 C54 C53 117.5(2) . . ? C55 C54 C57 122.3(2) . . ? C53 C54 C57 120.2(2) . . ? C56 C55 C54 119.2(2) . . ? C56 C55 H55 120.4 . . ? C54 C55 H55 120.4 . . ? N51 C56 C55 124.2(2) . . ? N51 C56 H56 117.9 . . ? C55 C56 H56 117.9 . . ? C54 C57 H57A 109.5 . . ? C54 C57 H57B 109.5 . . ? H57A C57 H57B 109.5 . . ? C54 C57 H57C 109.5 . . ? H57A C57 H57C 109.5 . . ? H57B C57 H57C 109.5 . . ? C54 C57 H57D 109.5 . . ? H57A C57 H57D 141.1 . . ? H57B C57 H57D 56.3 . . ? H57C C57 H57D 56.3 . . ? C54 C57 H57E 109.5 . . ? H57A C57 H57E 56.3 . . ? H57B C57 H57E 141.1 . . ? H57C C57 H57E 56.3 . . ? H57D C57 H57E 109.5 . . ? C54 C57 H57F 109.5 . . ? H57A C57 H57F 56.3 . . ? H57B C57 H57F 56.3 . . ? H57C C57 H57F 141.1 . . ? H57D C57 H57F 109.5 . . ? H57E C57 H57F 109.5 . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C21 N2 C3 N3 6.1(3) . . . . ? C21 N2 C3 C4 -174.1(2) . . . . ? N2 C3 N3 C31 6.7(3) . . . . ? C4 C3 N3 C31 -173.1(2) . . . . ? N3 C3 C4 O4 177.0(2) . . . . ? N2 C3 C4 O4 -2.8(2) . . . . ? N3 C3 C4 N5 -1.7(2) . . . . ? N2 C3 C4 N5 178.5(2) . . . . ? O4 C4 N5 C52 1.0(3) . . . . ? C3 C4 N5 C52 179.7(2) . . . . ? C3 N2 C21 C26 53.9(3) . . . . ? C3 N2 C21 C22 -126.0(2) . . . . ? C26 C21 C22 C23 -3.0(3) . . . . ? N2 C21 C22 C23 176.9(2) . . . . ? C21 C22 C23 C24 -0.1(3) . . . . ? C22 C23 C24 C25 2.2(3) . . . . ? C23 C24 C25 C26 -1.2(3) . . . . ? C22 C21 C26 C25 4.1(3) . . . . ? N2 C21 C26 C25 -175.8(2) . . . . ? C24 C25 C26 C21 -1.9(3) . . . . ? C3 N3 C31 C36 56.7(2) . . . . ? C3 N3 C31 C32 -126.4(2) . . . . ? C36 C31 C32 C33 -4.5(3) . . . . ? N3 C31 C32 C33 178.5(2) . . . . ? C31 C32 C33 C34 2.0(3) . . . . ? C32 C33 C34 C35 1.2(3) . . . . ? C33 C34 C35 C36 -1.8(3) . . . . ? C32 C31 C36 C35 3.8(3) . . . . ? N3 C31 C36 C35 -179.2(2) . . . . ? C34 C35 C36 C31 -0.7(3) . . . . ? C56 N51 C52 C53 -0.8(3) . . . . ? C56 N51 C52 N5 179.0(2) . . . . ? C4 N5 C52 N51 -176.9(2) . . . . ? C4 N5 C52 C53 2.9(3) . . . . ? N51 C52 C53 C54 1.0(3) . . . . ? N5 C52 C53 C54 -178.9(2) . . . . ? C52 C53 C54 C55 -0.4(3) . . . . ? C52 C53 C54 C57 179.7(2) . . . . ? C53 C54 C55 C56 -0.4(3) . . . . ? C57 C54 C55 C56 179.6(2) . . . . ? C52 N51 C56 C55 -0.1(3) . . . . ? C54 C55 C56 N51 0.6(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag N2 H2 O4 0.88(1) 2.18(2) 2.634(2) 111(2) . Y N2 H2 N51 0.88(1) 2.21(2) 3.026(2) 155(2) 4_565 Y N5 H5 N3 0.88(1) 2.17(2) 2.646(2) 113(1) . Y _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.139 _refine_diff_density_min -0.148 _refine_diff_density_rms 0.032 #============================================================================= data_(11a) #TrackingRef 'Trzewik_cif.txt' _database_code_depnum_ccdc_archive 'CCDC 750331' _audit_creation_method SHELXL-97 #============================================================================= _chemical_name_systematic ; N-Pyridin-2-yl-5H-dibenzo[d,f][1,3]diazepine-6-carboxamide ; _chemical_name_common N-Pyridin-2-yl-5H-dibenzo(d,f)(1,3)diazepine-6-carboxamide _chemical_melting_point '453-455 K' _chemical_formula_moiety 'C19 H14 N4 O' _chemical_formula_sum 'C19 H14 N4 O' _chemical_formula_weight 314.34 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 Triclinic _symmetry_space_group_name_H-M 'P -1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.3641(2) _cell_length_b 11.7961(3) _cell_length_c 14.4961(4) _cell_angle_alpha 89.766(1) _cell_angle_beta 69.834(1) _cell_angle_gamma 70.166(1) _cell_volume 1552.07(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4647 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 26.022 _exptl_crystal_description needle _exptl_crystal_colour orange _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.345 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9777 _exptl_absorpt_correction_T_max 0.9957 _exptl_absorpt_process_details 'HKL DENZO and Scalepack (Otwinowski & Minor, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f and \o scans to fill Ewald sphere' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9212 _diffrn_reflns_av_R_equivalents 0.0333 _diffrn_reflns_av_sigmaI/netI 0.0710 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.53 _diffrn_reflns_theta_max 26.00 _reflns_number_total 6016 _reflns_number_gt 3947 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL DENZO and Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR-92 (ALTOMARE et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep3 (Farrugia,1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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. H-atoms attached to four N-atoms (N2A, N5A, N2B, and N5B) were located on the Fourier difference maps and were refined using DFIX restraints with the target value of the N-H bond length 0.88 \%A with an assumed estimated standard deviation of 0.01 \%A (according to SHELX97 program instructions). ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0402P)^2^+0.4713P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6016 _refine_ls_number_parameters 445 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.1077 _refine_ls_R_factor_gt 0.0609 _refine_ls_wR_factor_ref 0.1289 _refine_ls_wR_factor_gt 0.1118 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.047 _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 N3A N 1.2300(2) 1.01162(17) 0.20012(14) 0.0446(5) Uani 1 1 d . . . C3A C 1.0918(2) 1.03338(19) 0.23184(16) 0.0386(5) Uani 1 1 d . . . N2A N 0.9838(2) 1.11332(17) 0.20494(14) 0.0417(5) Uani 1 1 d D . . H2A H 0.8944(14) 1.114(2) 0.2416(14) 0.050 Uiso 1 1 d D . . C4A C 1.0323(2) 0.9671(2) 0.31676(16) 0.0400(5) Uani 1 1 d . . . O4A O 0.90345(17) 0.97598(15) 0.34740(12) 0.0552(5) Uani 1 1 d . . . N5A N 1.1341(2) 0.90154(17) 0.35312(14) 0.0437(5) Uani 1 1 d D . . H5A H 1.2232(14) 0.905(2) 0.3253(15) 0.052 Uiso 1 1 d D . . C31A C 1.2995(2) 1.0822(2) 0.13682(17) 0.0444(6) Uani 1 1 d . . . C32A C 1.4234(3) 1.0865(3) 0.1522(2) 0.0630(7) Uani 1 1 d . . . H32A H 1.4538 1.0420 0.1989 0.076 Uiso 1 1 calc R . . C33A C 1.5017(3) 1.1543(3) 0.1003(2) 0.0745(9) Uani 1 1 d . . . H33A H 1.5832 1.1566 0.1125 0.089 Uiso 1 1 calc R . . C34A C 1.4592(3) 1.2184(3) 0.0308(2) 0.0644(8) Uani 1 1 d . . . H34A H 1.5114 1.2649 -0.0046 0.077 Uiso 1 1 calc R . . C35A C 1.3385(3) 1.2140(2) 0.01298(18) 0.0507(6) Uani 1 1 d . . . H35A H 1.3109 1.2580 -0.0348 0.061 Uiso 1 1 calc R . . C36A C 1.2564(2) 1.14591(19) 0.06428(16) 0.0407(5) Uani 1 1 d . . . C21A C 1.0021(2) 1.13354(18) 0.10543(16) 0.0365(5) Uani 1 1 d . . . C22A C 0.8845(2) 1.1424(2) 0.07697(17) 0.0440(6) Uani 1 1 d . . . H22A H 0.7987 1.1378 0.1233 0.053 Uiso 1 1 calc R . . C23A C 0.8927(3) 1.1580(2) -0.01879(18) 0.0489(6) Uani 1 1 d . . . H23A H 0.8124 1.1656 -0.0366 0.059 Uiso 1 1 calc R . . C24A C 1.0203(3) 1.1622(2) -0.08795(19) 0.0514(6) Uani 1 1 d . . . H24A H 1.0283 1.1700 -0.1534 0.062 Uiso 1 1 calc R . . C25A C 1.1368(3) 1.1546(2) -0.05910(17) 0.0482(6) Uani 1 1 d . . . H25A H 1.2229 1.1574 -0.1064 0.058 Uiso 1 1 calc R . . C26A C 1.1304(2) 1.14298(19) 0.03769(16) 0.0389(5) Uani 1 1 d . . . N51A N 1.2429(2) 0.75878(17) 0.43685(14) 0.0467(5) Uani 1 1 d . . . C52A C 1.1161(2) 0.83275(19) 0.43254(16) 0.0388(5) Uani 1 1 d . . . C53A C 0.9795(3) 0.8419(2) 0.50108(17) 0.0476(6) Uani 1 1 d . . . H53A H 0.8927 0.8961 0.4971 0.057 Uiso 1 1 calc R . . C54A C 0.9769(3) 0.7684(3) 0.57476(19) 0.0602(7) Uani 1 1 d . . . H54A H 0.8873 0.7710 0.6211 0.072 Uiso 1 1 calc R . . C55A C 1.1068(3) 0.6910(3) 0.5799(2) 0.0643(7) Uani 1 1 d . . . H55A H 1.1069 0.6404 0.6293 0.077 Uiso 1 1 calc R . . C56A C 1.2361(3) 0.6903(2) 0.51029(19) 0.0566(7) Uani 1 1 d . . . H56A H 1.3241 0.6392 0.5146 0.068 Uiso 1 1 calc R . . N3B N 0.7725(2) 0.77048(16) 0.29510(13) 0.0411(4) Uani 1 1 d . . . C3B C 0.6346(2) 0.79098(19) 0.32163(15) 0.0376(5) Uani 1 1 d . . . N2B N 0.5655(2) 0.70978(17) 0.32239(14) 0.0438(5) Uani 1 1 d D . . H2B H 0.4682(11) 0.7435(19) 0.3529(15) 0.053 Uiso 1 1 d D . . C4B C 0.5321(2) 0.9221(2) 0.35676(16) 0.0394(5) Uani 1 1 d . . . O4B O 0.39878(17) 0.95076(14) 0.38238(13) 0.0558(5) Uani 1 1 d . . . N5B N 0.6025(2) 1.00062(16) 0.35411(15) 0.0438(5) Uani 1 1 d D . . H5B H 0.7003(11) 0.9672(19) 0.3295(16) 0.053 Uiso 1 1 d D . . C31B C 0.8816(2) 0.65231(19) 0.26995(16) 0.0407(5) Uani 1 1 d . . . C32B C 1.0017(3) 0.6422(2) 0.29602(19) 0.0549(7) Uani 1 1 d . . . H32B H 1.0023 0.7098 0.3285 0.066 Uiso 1 1 calc R . . C33B C 1.1197(3) 0.5348(2) 0.2749(2) 0.0631(7) Uani 1 1 d . . . H33B H 1.1984 0.5296 0.2939 0.076 Uiso 1 1 calc R . . C34B C 1.1206(3) 0.4351(2) 0.2257(2) 0.0588(7) Uani 1 1 d . . . H34B H 1.1997 0.3618 0.2113 0.071 Uiso 1 1 calc R . . C35B C 1.0034(3) 0.4446(2) 0.19779(18) 0.0517(6) Uani 1 1 d . . . H35B H 1.0057 0.3770 0.1635 0.062 Uiso 1 1 calc R . . C36B C 0.8807(2) 0.55252(19) 0.21935(16) 0.0409(5) Uani 1 1 d . . . C21B C 0.6113(3) 0.62488(19) 0.23769(17) 0.0417(5) Uani 1 1 d . . . C22B C 0.5019(3) 0.6133(2) 0.20775(19) 0.0538(6) Uani 1 1 d . . . H22B H 0.4037 0.6592 0.2439 0.065 Uiso 1 1 calc R . . C23B C 0.5372(3) 0.5349(2) 0.1254(2) 0.0665(8) Uani 1 1 d . . . H23B H 0.4631 0.5250 0.1078 0.080 Uiso 1 1 calc R . . C24B C 0.6822(4) 0.4714(2) 0.0697(2) 0.0687(8) Uani 1 1 d . . . H24B H 0.7070 0.4215 0.0120 0.082 Uiso 1 1 calc R . . C25B C 0.7911(3) 0.4815(2) 0.09924(19) 0.0575(7) Uani 1 1 d . . . H25B H 0.8890 0.4373 0.0609 0.069 Uiso 1 1 calc R . . C26B C 0.7595(3) 0.55576(19) 0.18481(17) 0.0426(6) Uani 1 1 d . . . N51B N 0.6309(2) 1.18128(17) 0.31378(15) 0.0493(5) Uani 1 1 d . . . C52B C 0.5404(2) 1.12804(19) 0.36757(16) 0.0400(5) Uani 1 1 d . . . C53B C 0.3979(3) 1.1919(2) 0.43147(19) 0.0517(6) Uani 1 1 d . . . H53B H 0.3383 1.1519 0.4692 0.062 Uiso 1 1 calc R . . C54B C 0.3472(3) 1.3170(2) 0.4373(2) 0.0651(8) Uani 1 1 d . . . H54B H 0.2517 1.3629 0.4791 0.078 Uiso 1 1 calc R . . C55B C 0.4379(3) 1.3731(2) 0.3812(2) 0.0658(8) Uani 1 1 d . . . H55B H 0.4051 1.4572 0.3836 0.079 Uiso 1 1 calc R . . C56B C 0.5781(3) 1.3022(2) 0.3215(2) 0.0595(7) Uani 1 1 d . . . H56B H 0.6400 1.3407 0.2843 0.071 Uiso 1 1 calc 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 N3A 0.0376(11) 0.0515(12) 0.0461(12) 0.0139(9) -0.0157(10) -0.0175(10) C3A 0.0358(13) 0.0410(12) 0.0387(13) 0.0037(10) -0.0142(11) -0.0127(10) N2A 0.0313(10) 0.0505(11) 0.0391(12) 0.0074(9) -0.0105(9) -0.0121(9) C4A 0.0366(13) 0.0437(13) 0.0414(13) 0.0024(10) -0.0147(11) -0.0160(11) O4A 0.0390(10) 0.0745(12) 0.0623(11) 0.0226(9) -0.0227(9) -0.0288(9) N5A 0.0342(11) 0.0518(12) 0.0465(12) 0.0150(9) -0.0143(10) -0.0178(10) C31A 0.0366(13) 0.0489(14) 0.0472(14) 0.0073(11) -0.0146(12) -0.0154(11) C32A 0.0412(15) 0.094(2) 0.0627(18) 0.0306(16) -0.0254(14) -0.0282(15) C33A 0.0479(17) 0.115(3) 0.084(2) 0.0399(19) -0.0340(16) -0.0472(17) C34A 0.0494(16) 0.086(2) 0.0729(19) 0.0301(16) -0.0247(15) -0.0405(15) C35A 0.0467(15) 0.0575(15) 0.0547(16) 0.0177(12) -0.0213(13) -0.0243(13) C36A 0.0333(12) 0.0435(13) 0.0439(14) 0.0043(11) -0.0113(11) -0.0150(11) C21A 0.0362(13) 0.0325(11) 0.0396(13) 0.0031(9) -0.0146(11) -0.0100(10) C22A 0.0370(13) 0.0470(14) 0.0470(15) 0.0064(11) -0.0158(12) -0.0135(11) C23A 0.0462(15) 0.0522(15) 0.0560(16) 0.0084(12) -0.0278(14) -0.0175(12) C24A 0.0605(17) 0.0568(16) 0.0461(15) 0.0124(12) -0.0251(14) -0.0266(13) C25A 0.0503(15) 0.0554(15) 0.0442(15) 0.0123(11) -0.0164(13) -0.0263(12) C26A 0.0406(13) 0.0383(12) 0.0408(13) 0.0063(10) -0.0169(11) -0.0160(11) N51A 0.0429(12) 0.0501(12) 0.0473(12) 0.0117(10) -0.0184(10) -0.0152(10) C52A 0.0411(14) 0.0418(13) 0.0384(13) 0.0058(10) -0.0154(11) -0.0200(11) C53A 0.0416(14) 0.0600(15) 0.0437(15) 0.0077(12) -0.0134(12) -0.0233(12) C54A 0.0591(18) 0.0809(19) 0.0450(16) 0.0117(14) -0.0101(14) -0.0397(16) C55A 0.075(2) 0.0728(19) 0.0493(17) 0.0238(14) -0.0210(16) -0.0341(17) C56A 0.0616(18) 0.0554(16) 0.0540(17) 0.0167(13) -0.0268(15) -0.0169(13) N3B 0.0366(11) 0.0395(11) 0.0430(11) 0.0013(8) -0.0099(9) -0.0134(9) C3B 0.0360(13) 0.0423(13) 0.0341(12) 0.0056(10) -0.0098(10) -0.0168(11) N2B 0.0370(11) 0.0442(11) 0.0480(12) 0.0005(9) -0.0089(10) -0.0188(10) C4B 0.0359(13) 0.0447(13) 0.0393(13) 0.0071(10) -0.0139(11) -0.0163(11) O4B 0.0351(10) 0.0509(10) 0.0779(12) 0.0023(9) -0.0166(9) -0.0154(8) N5B 0.0320(10) 0.0387(11) 0.0582(13) 0.0022(9) -0.0141(10) -0.0122(9) C31B 0.0365(13) 0.0382(13) 0.0435(14) 0.0056(10) -0.0103(11) -0.0133(11) C32B 0.0449(15) 0.0548(16) 0.0653(18) -0.0007(13) -0.0204(14) -0.0177(13) C33B 0.0438(16) 0.0636(18) 0.080(2) 0.0078(15) -0.0264(15) -0.0134(14) C34B 0.0463(16) 0.0476(15) 0.0713(19) 0.0101(13) -0.0187(14) -0.0060(12) C35B 0.0506(16) 0.0408(14) 0.0552(16) 0.0032(11) -0.0144(13) -0.0113(12) C36B 0.0400(13) 0.0390(13) 0.0392(13) 0.0066(10) -0.0092(11) -0.0143(11) C21B 0.0474(14) 0.0348(12) 0.0449(14) 0.0066(10) -0.0170(12) -0.0171(11) C22B 0.0537(16) 0.0512(15) 0.0655(17) 0.0082(13) -0.0282(14) -0.0233(13) C23B 0.076(2) 0.0581(17) 0.082(2) 0.0026(15) -0.0462(18) -0.0264(16) C24B 0.090(2) 0.0537(17) 0.0683(19) -0.0061(14) -0.0438(19) -0.0173(16) C25B 0.0636(17) 0.0444(14) 0.0579(17) -0.0026(12) -0.0250(15) -0.0087(13) C26B 0.0474(15) 0.0351(12) 0.0452(14) 0.0053(10) -0.0160(12) -0.0153(11) N51B 0.0471(12) 0.0417(12) 0.0570(13) 0.0062(9) -0.0157(11) -0.0167(10) C52B 0.0385(13) 0.0396(13) 0.0452(14) 0.0039(10) -0.0182(12) -0.0149(11) C53B 0.0395(14) 0.0500(15) 0.0580(16) -0.0005(12) -0.0118(13) -0.0128(12) C54B 0.0463(16) 0.0523(17) 0.076(2) -0.0088(14) -0.0139(15) -0.0011(14) C55B 0.071(2) 0.0392(15) 0.083(2) 0.0061(14) -0.0318(18) -0.0120(15) C56B 0.0628(19) 0.0448(16) 0.0710(19) 0.0122(13) -0.0225(16) -0.0215(14) _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 N3A C3A 1.275(3) . ? N3A C31A 1.414(3) . ? C3A N2A 1.370(3) . ? C3A C4A 1.517(3) . ? N2A C21A 1.419(3) . ? N2A H2A 0.891(10) . ? C4A O4A 1.220(2) . ? C4A N5A 1.347(3) . ? N5A C52A 1.402(3) . ? N5A H5A 0.886(10) . ? C31A C32A 1.393(3) . ? C31A C36A 1.400(3) . ? C32A C33A 1.371(4) . ? C32A H32A 0.9300 . ? C33A C34A 1.362(4) . ? C33A H33A 0.9300 . ? C34A C35A 1.378(3) . ? C34A H34A 0.9300 . ? C35A C36A 1.395(3) . ? C35A H35A 0.9300 . ? C36A C26A 1.494(3) . ? C21A C22A 1.388(3) . ? C21A C26A 1.395(3) . ? C22A C23A 1.376(3) . ? C22A H22A 0.9300 . ? C23A C24A 1.373(3) . ? C23A H23A 0.9300 . ? C24A C25A 1.384(3) . ? C24A H24A 0.9300 . ? C25A C26A 1.390(3) . ? C25A H25A 0.9300 . ? N51A C56A 1.330(3) . ? N51A C52A 1.330(3) . ? C52A C53A 1.389(3) . ? C53A C54A 1.372(3) . ? C53A H53A 0.9300 . ? C54A C55A 1.374(4) . ? C54A H54A 0.9300 . ? C55A C56A 1.369(4) . ? C55A H55A 0.9300 . ? C56A H56A 0.9300 . ? N3B C3B 1.279(3) . ? N3B C31B 1.416(3) . ? C3B N2B 1.375(3) . ? C3B C4B 1.517(3) . ? N2B C21B 1.422(3) . ? N2B H2B 0.891(9) . ? C4B O4B 1.221(2) . ? C4B N5B 1.352(3) . ? N5B C52B 1.404(3) . ? N5B H5B 0.889(10) . ? C31B C32B 1.390(3) . ? C31B C36B 1.394(3) . ? C32B C33B 1.374(3) . ? C32B H32B 0.9300 . ? C33B C34B 1.374(4) . ? C33B H33B 0.9300 . ? C34B C35B 1.378(3) . ? C34B H34B 0.9300 . ? C35B C36B 1.403(3) . ? C35B H35B 0.9300 . ? C36B C26B 1.494(3) . ? C21B C22B 1.392(3) . ? C21B C26B 1.398(3) . ? C22B C23B 1.375(3) . ? C22B H22B 0.9300 . ? C23B C24B 1.369(4) . ? C23B H23B 0.9300 . ? C24B C25B 1.377(4) . ? C24B H24B 0.9300 . ? C25B C26B 1.396(3) . ? C25B H25B 0.9300 . ? N51B C52B 1.332(3) . ? N51B C56B 1.333(3) . ? C52B C53B 1.384(3) . ? C53B C54B 1.380(3) . ? C53B H53B 0.9300 . ? C54B C55B 1.369(4) . ? C54B H54B 0.9300 . ? C55B C56B 1.369(4) . ? C55B H55B 0.9300 . ? C56B H56B 0.9300 . ? 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 C3A N3A C31A 124.23(19) . . ? N3A C3A N2A 130.2(2) . . ? N3A C3A C4A 116.68(19) . . ? N2A C3A C4A 113.05(19) . . ? C3A N2A C21A 123.44(18) . . ? C3A N2A H2A 112.2(15) . . ? C21A N2A H2A 114.2(15) . . ? O4A C4A N5A 125.3(2) . . ? O4A C4A C3A 121.2(2) . . ? N5A C4A C3A 113.52(19) . . ? C4A N5A C52A 128.49(19) . . ? C4A N5A H5A 116.1(15) . . ? C52A N5A H5A 115.3(15) . . ? C32A C31A C36A 119.1(2) . . ? C32A C31A N3A 113.6(2) . . ? C36A C31A N3A 127.33(19) . . ? C33A C32A C31A 121.9(2) . . ? C33A C32A H32A 119.1 . . ? C31A C32A H32A 119.1 . . ? C34A C33A C32A 119.5(2) . . ? C34A C33A H33A 120.2 . . ? C32A C33A H33A 120.2 . . ? C33A C34A C35A 119.8(2) . . ? C33A C34A H34A 120.1 . . ? C35A C34A H34A 120.1 . . ? C34A C35A C36A 122.2(2) . . ? C34A C35A H35A 118.9 . . ? C36A C35A H35A 118.9 . . ? C35A C36A C31A 117.51(19) . . ? C35A C36A C26A 118.59(19) . . ? C31A C36A C26A 123.88(19) . . ? C22A C21A C26A 120.4(2) . . ? C22A C21A N2A 116.40(19) . . ? C26A C21A N2A 123.16(18) . . ? C23A C22A C21A 121.0(2) . . ? C23A C22A H22A 119.5 . . ? C21A C22A H22A 119.5 . . ? C24A C23A C22A 119.6(2) . . ? C24A C23A H23A 120.2 . . ? C22A C23A H23A 120.2 . . ? C23A C24A C25A 119.2(2) . . ? C23A C24A H24A 120.4 . . ? C25A C24A H24A 120.4 . . ? C24A C25A C26A 122.7(2) . . ? C24A C25A H25A 118.7 . . ? C26A C25A H25A 118.7 . . ? C25A C26A C21A 116.93(19) . . ? C25A C26A C36A 119.1(2) . . ? C21A C26A C36A 123.89(19) . . ? C56A N51A C52A 117.5(2) . . ? N51A C52A C53A 123.1(2) . . ? N51A C52A N5A 113.41(19) . . ? C53A C52A N5A 123.5(2) . . ? C54A C53A C52A 117.8(2) . . ? C54A C53A H53A 121.1 . . ? C52A C53A H53A 121.1 . . ? C53A C54A C55A 119.8(2) . . ? C53A C54A H54A 120.1 . . ? C55A C54A H54A 120.1 . . ? C56A C55A C54A 118.2(2) . . ? C56A C55A H55A 120.9 . . ? C54A C55A H55A 120.9 . . ? N51A C56A C55A 123.6(2) . . ? N51A C56A H56A 118.2 . . ? C55A C56A H56A 118.2 . . ? C3B N3B C31B 123.40(18) . . ? N3B C3B N2B 128.7(2) . . ? N3B C3B C4B 116.39(18) . . ? N2B C3B C4B 114.90(18) . . ? C3B N2B C21B 120.95(19) . . ? C3B N2B H2B 112.2(15) . . ? C21B N2B H2B 114.1(15) . . ? O4B C4B N5B 125.0(2) . . ? O4B C4B C3B 121.11(19) . . ? N5B C4B C3B 113.89(19) . . ? C4B N5B C52B 127.01(19) . . ? C4B N5B H5B 114.8(15) . . ? C52B N5B H5B 117.0(15) . . ? C32B C31B C36B 119.8(2) . . ? C32B C31B N3B 113.66(19) . . ? C36B C31B N3B 126.44(19) . . ? C33B C32B C31B 121.6(2) . . ? C33B C32B H32B 119.2 . . ? C31B C32B H32B 119.2 . . ? C34B C33B C32B 119.5(2) . . ? C34B C33B H33B 120.2 . . ? C32B C33B H33B 120.2 . . ? C33B C34B C35B 119.4(2) . . ? C33B C34B H34B 120.3 . . ? C35B C34B H34B 120.3 . . ? C34B C35B C36B 122.3(2) . . ? C34B C35B H35B 118.9 . . ? C36B C35B H35B 118.9 . . ? C31B C36B C35B 117.3(2) . . ? C31B C36B C26B 123.8(2) . . ? C35B C36B C26B 118.9(2) . . ? C22B C21B C26B 120.3(2) . . ? C22B C21B N2B 117.3(2) . . ? C26B C21B N2B 122.38(19) . . ? C23B C22B C21B 120.9(2) . . ? C23B C22B H22B 119.6 . . ? C21B C22B H22B 119.6 . . ? C24B C23B C22B 119.6(2) . . ? C24B C23B H23B 120.2 . . ? C22B C23B H23B 120.2 . . ? C23B C24B C25B 119.9(2) . . ? C23B C24B H24B 120.1 . . ? C25B C24B H24B 120.1 . . ? C24B C25B C26B 122.2(3) . . ? C24B C25B H25B 118.9 . . ? C26B C25B H25B 118.9 . . ? C25B C26B C21B 117.0(2) . . ? C25B C26B C36B 119.8(2) . . ? C21B C26B C36B 123.1(2) . . ? C52B N51B C56B 117.2(2) . . ? N51B C52B C53B 123.4(2) . . ? N51B C52B N5B 114.0(2) . . ? C53B C52B N5B 122.6(2) . . ? C54B C53B C52B 117.7(2) . . ? C54B C53B H53B 121.2 . . ? C52B C53B H53B 121.2 . . ? C55B C54B C53B 119.7(3) . . ? C55B C54B H54B 120.1 . . ? C53B C54B H54B 120.1 . . ? C56B C55B C54B 118.3(2) . . ? C56B C55B H55B 120.8 . . ? C54B C55B H55B 120.8 . . ? N51B C56B C55B 123.7(2) . . ? N51B C56B H56B 118.2 . . ? C55B C56B H56B 118.2 . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C31A N3A C3A N2A 9.8(4) . . . . ? C31A N3A C3A C4A -166.32(19) . . . . ? N3A C3A N2A C21A 40.7(3) . . . . ? C4A C3A N2A C21A -143.09(19) . . . . ? N3A C3A C4A O4A -175.0(2) . . . . ? N2A C3A C4A O4A 8.3(3) . . . . ? N3A C3A C4A N5A 5.7(3) . . . . ? N2A C3A C4A N5A -171.08(18) . . . . ? O4A C4A N5A C52A -1.3(4) . . . . ? C3A C4A N5A C52A 178.0(2) . . . . ? C3A N3A C31A C32A 148.1(2) . . . . ? C3A N3A C31A C36A -31.3(4) . . . . ? C36A C31A C32A C33A 2.0(4) . . . . ? N3A C31A C32A C33A -177.4(3) . . . . ? C31A C32A C33A C34A -0.9(5) . . . . ? C32A C33A C34A C35A -0.2(5) . . . . ? C33A C34A C35A C36A 0.2(4) . . . . ? C34A C35A C36A C31A 0.9(4) . . . . ? C34A C35A C36A C26A -177.9(2) . . . . ? C32A C31A C36A C35A -2.0(3) . . . . ? N3A C31A C36A C35A 177.4(2) . . . . ? C32A C31A C36A C26A 176.8(2) . . . . ? N3A C31A C36A C26A -3.9(4) . . . . ? C3A N2A C21A C22A 137.6(2) . . . . ? C3A N2A C21A C26A -41.6(3) . . . . ? C26A C21A C22A C23A 1.4(3) . . . . ? N2A C21A C22A C23A -177.8(2) . . . . ? C21A C22A C23A C24A 1.4(3) . . . . ? C22A C23A C24A C25A -2.1(3) . . . . ? C23A C24A C25A C26A -0.1(4) . . . . ? C24A C25A C26A C21A 2.9(3) . . . . ? C24A C25A C26A C36A -174.9(2) . . . . ? C22A C21A C26A C25A -3.5(3) . . . . ? N2A C21A C26A C25A 175.8(2) . . . . ? C22A C21A C26A C36A 174.2(2) . . . . ? N2A C21A C26A C36A -6.6(3) . . . . ? C35A C36A C26A C25A 30.2(3) . . . . ? C31A C36A C26A C25A -148.5(2) . . . . ? C35A C36A C26A C21A -147.4(2) . . . . ? C31A C36A C26A C21A 33.9(3) . . . . ? C56A N51A C52A C53A 0.6(3) . . . . ? C56A N51A C52A N5A 179.71(19) . . . . ? C4A N5A C52A N51A 166.7(2) . . . . ? C4A N5A C52A C53A -14.2(3) . . . . ? N51A C52A C53A C54A -1.7(3) . . . . ? N5A C52A C53A C54A 179.3(2) . . . . ? C52A C53A C54A C55A 1.3(4) . . . . ? C53A C54A C55A C56A 0.2(4) . . . . ? C52A N51A C56A C55A 1.0(4) . . . . ? C54A C55A C56A N51A -1.4(4) . . . . ? C31B N3B C3B N2B -6.8(4) . . . . ? C31B N3B C3B C4B 173.50(18) . . . . ? N3B C3B N2B C21B -49.7(3) . . . . ? C4B C3B N2B C21B 130.0(2) . . . . ? N3B C3B C4B O4B 179.1(2) . . . . ? N2B C3B C4B O4B -0.7(3) . . . . ? N3B C3B C4B N5B 0.6(3) . . . . ? N2B C3B C4B N5B -179.13(19) . . . . ? O4B C4B N5B C52B -8.6(4) . . . . ? C3B C4B N5B C52B 169.8(2) . . . . ? C3B N3B C31B C32B -146.3(2) . . . . ? C3B N3B C31B C36B 36.9(3) . . . . ? C36B C31B C32B C33B -1.4(4) . . . . ? N3B C31B C32B C33B -178.3(2) . . . . ? C31B C32B C33B C34B 0.9(4) . . . . ? C32B C33B C34B C35B 0.3(4) . . . . ? C33B C34B C35B C36B -1.1(4) . . . . ? C32B C31B C36B C35B 0.6(3) . . . . ? N3B C31B C36B C35B 177.1(2) . . . . ? C32B C31B C36B C26B -177.6(2) . . . . ? N3B C31B C36B C26B -1.0(4) . . . . ? C34B C35B C36B C31B 0.7(3) . . . . ? C34B C35B C36B C26B 178.9(2) . . . . ? C3B N2B C21B C22B -132.9(2) . . . . ? C3B N2B C21B C26B 46.4(3) . . . . ? C26B C21B C22B C23B -0.6(4) . . . . ? N2B C21B C22B C23B 178.8(2) . . . . ? C21B C22B C23B C24B -2.9(4) . . . . ? C22B C23B C24B C25B 3.5(4) . . . . ? C23B C24B C25B C26B -0.5(4) . . . . ? C24B C25B C26B C21B -2.9(4) . . . . ? C24B C25B C26B C36B 173.1(2) . . . . ? C22B C21B C26B C25B 3.4(3) . . . . ? N2B C21B C26B C25B -175.9(2) . . . . ? C22B C21B C26B C36B -172.5(2) . . . . ? N2B C21B C26B C36B 8.2(3) . . . . ? C31B C36B C26B C25B 149.0(2) . . . . ? C35B C36B C26B C25B -29.1(3) . . . . ? C31B C36B C26B C21B -35.2(3) . . . . ? C35B C36B C26B C21B 146.7(2) . . . . ? C56B N51B C52B C53B -1.5(3) . . . . ? C56B N51B C52B N5B 178.7(2) . . . . ? C4B N5B C52B N51B -146.3(2) . . . . ? C4B N5B C52B C53B 33.9(3) . . . . ? N51B C52B C53B C54B 1.6(3) . . . . ? N5B C52B C53B C54B -178.6(2) . . . . ? C52B C53B C54B C55B -0.4(4) . . . . ? C53B C54B C55B C56B -0.8(4) . . . . ? C52B N51B C56B C55B 0.1(4) . . . . ? C54B C55B C56B N51B 1.0(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag N2A H2A O4A 0.89(1) 2.24(2) 2.699(2) 112(2) . ? N2A H2A N51B 0.89(1) 2.40(1) 3.248(3) 160(2) . ? N5A H5A O4B 0.89(1) 2.45(2) 3.151(2) 137(2) 1_655 ? N2B H2B N51A 0.89(1) 2.17(1) 3.023(3) 159(2) 1_455 ? N5B H5B N3B 0.89(1) 2.18(2) 2.634(3) 111(2) . ? N5B H5B O4A 0.89(1) 2.25(2) 3.000(2) 143(2) . ? N5A H5A N3A 0.89(1) 2.20(2) 2.631(3) 110(2) . ? N2B H2B O4B 0.89(1) 2.30(2) 2.734(2) 110(2) . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.187 _refine_diff_density_min -0.199 _refine_diff_density_rms 0.039 #==============================================================================