# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2006 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name _publ_author_address A.Briceno ; Centro de Quimica Instituto Venezolano de Investigaciones Cientifica (IVIC) Apartado 21827 Caracas 1020-A Venezuela ; 'Dayana Leal' ; Facultad de Ciencias Departamento de Quimica Univesidad de Los Andes Apartado 40 La Hechicera Merida 5251 Venezuela ; 'Reinaldo Atencio' ; Centro de Quimica Instituto Venezolano de Investigaciones Cientifica (IVIC) Apartado 21827 Caracas 1020-A Venezuela ; 'de Delgado,G.Diaz' ; Facultad de Ciencias Departamento de Quimica Univesidad de Los Andes Apartado 40 La Hechicera Merida 5251 Venezuela ; _publ_contact_author_address ; Centro de Quimica Instituto Venezolano de Investigaciones Cientifica (IVIC) Apartado 21827 Caracas 1020-A Venezuela ; _publ_contact_author_email abriceno@ivic.ve _publ_contact_author_fax '(58-212) 504-1350' _publ_contact_author_phone '(58-212) 504-1320' #========================================================================== _publ_contact_author_name 'Alexander Briceno' _publ_requested_category ? _publ_requested_coeditor_name ? #========================================================================== # TITLE AND AUTHOR LIST _publ_section_title ; Supramolecular isomerism in multivalent metal-templated assemblies with topochemical influence in the regioselective synthesis of tetrakis(2-pyridyl)cyclobutane isomers ; data_shelxl_compound_1 _database_code_depnum_ccdc_archive 'CCDC 606784' #======================================================== _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '4(C12 H10 N2), C2 H8 Mn N2 O4 S2' _chemical_formula_sum 'C50 H48 Mn N10 O4 S2' _chemical_formula_weight 972.04 _chemical_compound_source Synthesis 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' Mn Mn 0.3368 0.7283 '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' S S 0.1246 0.1234 '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 P2/n _symmetry_space_group_name_Hall '-P 2yac' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z-1/2' _cell_length_a 13.3756(18) _cell_length_b 12.0960(14) _cell_length_c 16.498(2) _cell_angle_alpha 90.00 _cell_angle_beta 110.314(3) _cell_angle_gamma 90.00 _cell_volume 2503.2(6) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 3419 _cell_measurement_theta_min 2.14 _cell_measurement_theta_max 28.01 _exptl_crystal_description Prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.290 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1014 _exptl_absorpt_coefficient_mu 0.401 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.820 _exptl_absorpt_correction_T_max 0.912 _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku AFC7S Mercury' _diffrn_measurement_method '\w ' _diffrn_radiation_detector CCD _diffrn_measurement_device ; Mercury (2x2 bin mode) ; _diffrn_detector_area_resol_mean 14.6306 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 28180 _diffrn_reflns_av_R_equivalents 0.0336 _diffrn_reflns_av_sigmaI/netI 0.0277 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 28.01 _reflns_number_total 5108 _reflns_number_gt 3663 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_cell_refinement 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_data_reduction 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_structure_solution 'SHELXLTL-NT V5.1 (Bruker AXS, 1998)' _computing_structure_refinement 'SHELXLTL-NT V5.1 (Bruker AXS, 1998)' _computing_molecular_graphics ; SHELXLTL-NT V5.1 (Bruker AXS, 1998) and DIAMOND (Brandenburg, 1998) ; _computing_publication_material ; SHELXLTL-NT V5.1 (Bruker AXS, 1998) and PLATON (Spek, 2003). ; _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^)+(0.0786P)^2^+1.2455P] 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 5108 _refine_ls_number_parameters 273 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0995 _refine_ls_R_factor_gt 0.0670 _refine_ls_wR_factor_ref 0.1817 _refine_ls_wR_factor_gt 0.1635 _refine_ls_goodness_of_fit_ref 1.098 _refine_ls_restrained_S_all 1.098 _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 Mn1 Mn 0.2500 -0.25185(4) 0.7500 0.0453(2) Uani 1 2 d S . . S1 S -0.05165(10) -0.24568(9) 0.85135(9) 0.0937(4) Uani 1 1 d . . . N1 N 0.0923(2) -0.2556(2) 0.7650(2) 0.0666(8) Uani 1 1 d . . . N2 N 0.0783(2) 0.4245(2) 0.73832(17) 0.0602(7) Uani 1 1 d . . . N3 N 0.3101(2) 0.0702(2) 0.64550(19) 0.0683(8) Uani 1 1 d . . . N4 N 0.1923(2) 0.5545(2) 0.51053(17) 0.0647(7) Uani 1 1 d . . . O1W O 0.1785(2) -0.25445(17) 0.60699(14) 0.0672(6) Uani 1 1 d . . . H1W1 H 0.1760 -0.3134 0.5788 0.081 Uiso 1 1 d R . . H2W1 H 0.1814 -0.2023 0.5776 0.081 Uiso 1 1 d R . . O2W O 0.2500 -0.4304(2) 0.7500 0.0590(8) Uani 1 2 d S . . H1W2 H 0.1950 -0.4808 0.7485 0.071 Uiso 1 1 d R . . O3W O 0.2500 -0.0745(2) 0.7500 0.0906(13) Uani 1 2 d S . . H1W3 H 0.2354 -0.0370 0.7851 0.109 Uiso 1 1 d R . . C1 C 0.0327(3) -0.2514(2) 0.8008(2) 0.0537(7) Uani 1 1 d . . . C2 C 0.1470(3) 0.3010(3) 0.65917(19) 0.0569(8) Uani 1 1 d . . . H2 H 0.1797 0.3595 0.6415 0.068 Uiso 1 1 calc R . . C3 C 0.1769(3) 0.1991(3) 0.64849(19) 0.0564(8) Uani 1 1 d . . . H3 H 0.1373 0.1409 0.6585 0.068 Uiso 1 1 calc R . . C4 C 0.0659(2) 0.3272(2) 0.69702(19) 0.0524(7) Uani 1 1 d . . . C5 C 0.0079(3) 0.4516(3) 0.7761(2) 0.0697(9) Uani 1 1 d . . . H5 H 0.0170 0.5183 0.8057 0.084 Uiso 1 1 calc R . . C6 C -0.0764(3) 0.3865(3) 0.7735(3) 0.0811(11) Uani 1 1 d . . . H6 H -0.1241 0.4088 0.7999 0.097 Uiso 1 1 calc R . . C7 C -0.0889(3) 0.2882(4) 0.7312(3) 0.0923(13) Uani 1 1 d . . . H7 H -0.1458 0.2422 0.7283 0.111 Uiso 1 1 calc R . . C8 C -0.0176(3) 0.2572(3) 0.6928(3) 0.0770(11) Uani 1 1 d . . . H8 H -0.0251 0.1898 0.6642 0.092 Uiso 1 1 calc R . . C9 C 0.2678(3) 0.1712(2) 0.62201(18) 0.0549(8) Uani 1 1 d . . . C10 C 0.3937(3) 0.0419(3) 0.6238(3) 0.0819(11) Uani 1 1 d . . . H10 H 0.4246 -0.0269 0.6413 0.098 Uiso 1 1 calc R . . C11 C 0.4366(3) 0.1081(4) 0.5773(3) 0.0852(11) Uani 1 1 d . . . H11 H 0.4937 0.0837 0.5621 0.102 Uiso 1 1 calc R . . C12 C 0.3940(4) 0.2107(4) 0.5535(3) 0.0865(12) Uani 1 1 d . . . H12 H 0.4218 0.2580 0.5223 0.104 Uiso 1 1 calc R . . C13 C 0.3092(3) 0.2425(3) 0.5766(2) 0.0710(10) Uani 1 1 d . . . H13 H 0.2795 0.3124 0.5616 0.085 Uiso 1 1 calc R . . C14 C 0.0137(3) 0.4744(3) 0.4713(2) 0.0649(9) Uani 1 1 d . . . H14 H -0.0367 0.4287 0.4328 0.078 Uiso 1 1 calc R . . C15 C 0.1196(3) 0.4829(3) 0.4622(2) 0.0579(8) Uani 1 1 d . . . C16 C 0.2875(3) 0.5560(3) 0.5005(3) 0.0779(10) Uani 1 1 d . . . H16 H 0.3388 0.6050 0.5341 0.093 Uiso 1 1 calc R . . C17 C 0.3137(3) 0.4893(4) 0.4433(3) 0.0827(12) Uani 1 1 d . . . H17 H 0.3814 0.4922 0.4395 0.099 Uiso 1 1 calc R . . C18 C 0.2385(3) 0.4190(4) 0.3924(3) 0.0823(12) Uani 1 1 d . . . H18 H 0.2531 0.3745 0.3519 0.099 Uiso 1 1 calc R . . C19 C 0.1405(3) 0.4150(3) 0.4020(2) 0.0685(9) Uani 1 1 d . . . H19 H 0.0883 0.3670 0.3682 0.082 Uiso 1 1 calc R . . C20 C -0.0115(6) -0.0269(6) 0.5305(4) 0.0620(15) Uiso 0.55 1 d P . 1 H20 H 0.0338 -0.0845 0.5577 0.074 Uiso 0.55 1 calc PR . 1 C21 C -0.0984(4) -0.0055(6) 0.5584(4) 0.072(2) Uiso 0.55 1 d PG A 1 N5 N -0.1661(5) 0.0822(5) 0.5218(3) 0.0664(19) Uiso 0.55 1 d PG A 1 C22 C -0.2481(5) 0.1093(5) 0.5519(4) 0.074(2) Uiso 0.55 1 d PG A 1 H22 H -0.2934 0.1680 0.5274 0.088 Uiso 0.55 1 calc PR A 1 C23 C -0.2623(5) 0.0486(7) 0.6186(5) 0.100(4) Uiso 0.55 1 d PG A 1 H23 H -0.3171 0.0667 0.6388 0.120 Uiso 0.55 1 calc PR A 1 C24 C -0.1945(6) -0.0391(6) 0.6553(4) 0.094(3) Uiso 0.55 1 d PG A 1 H24 H -0.2040 -0.0797 0.6999 0.113 Uiso 0.55 1 calc PR A 1 C25 C -0.1126(5) -0.0662(5) 0.6252(5) 0.087(3) Uiso 0.55 1 d PG A 1 H25 H -0.0673 -0.1249 0.6497 0.105 Uiso 0.55 1 calc PR A 1 C20A C -0.0413(6) 0.0293(7) 0.4931(6) 0.066(2) Uiso 0.45 1 d P . 2 H20A H -0.0582 0.0788 0.4472 0.079 Uiso 0.45 1 calc PR . 2 C21A C -0.1118(6) 0.0257(7) 0.5428(5) 0.066(2) Uiso 0.45 1 d PG B 2 N5A N -0.1955(7) 0.1010(6) 0.5202(4) 0.073(3) Uiso 0.45 1 d PG B 2 C22A C -0.2692(6) 0.0991(7) 0.5624(6) 0.108(5) Uiso 0.45 1 d PG B 2 H22A H -0.3252 0.1494 0.5473 0.129 Uiso 0.45 1 calc PR B 2 C23A C -0.2592(7) 0.0219(9) 0.6272(6) 0.090(4) Uiso 0.45 1 d PG B 2 H23A H -0.3085 0.0206 0.6554 0.109 Uiso 0.45 1 calc PR B 2 C24A C -0.1754(8) -0.0534(8) 0.6498(6) 0.111(5) Uiso 0.45 1 d PG B 2 H24A H -0.1687 -0.1050 0.6931 0.134 Uiso 0.45 1 calc PR B 2 C25A C -0.1017(6) -0.0515(7) 0.6076(6) 0.097(4) Uiso 0.45 1 d PG B 2 H25A H -0.0457 -0.1018 0.6227 0.117 Uiso 0.45 1 calc PR B 2 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 Mn1 0.0552(4) 0.0353(3) 0.0562(4) 0.000 0.0328(3) 0.000 S1 0.1046(8) 0.0894(7) 0.1279(10) 0.0033(6) 0.0921(8) -0.0009(6) N1 0.0643(17) 0.0654(18) 0.087(2) 0.0025(14) 0.0470(16) 0.0019(13) N2 0.0667(16) 0.0443(14) 0.0681(16) 0.0009(13) 0.0216(14) 0.0011(12) N3 0.086(2) 0.0472(15) 0.0806(19) -0.0022(14) 0.0400(16) 0.0047(14) N4 0.0668(17) 0.0730(18) 0.0571(16) 0.0010(14) 0.0250(14) 0.0095(15) O1W 0.0918(17) 0.0593(13) 0.0557(13) 0.0048(10) 0.0323(12) 0.0076(11) O2W 0.0653(18) 0.0327(14) 0.091(2) 0.000 0.0426(17) 0.000 O3W 0.149(3) 0.0338(15) 0.134(3) 0.000 0.106(3) 0.000 C1 0.0582(18) 0.0434(15) 0.0696(19) 0.0000(14) 0.0349(16) -0.0040(14) C2 0.0639(19) 0.0520(18) 0.0476(16) 0.0001(14) 0.0102(15) -0.0009(15) C3 0.0639(19) 0.0509(17) 0.0487(16) -0.0027(14) 0.0125(14) -0.0033(15) C4 0.0533(17) 0.0485(16) 0.0494(16) -0.0023(13) 0.0103(13) 0.0015(14) C5 0.080(2) 0.0541(19) 0.077(2) -0.0023(17) 0.030(2) 0.0056(18) C6 0.076(2) 0.081(3) 0.096(3) -0.008(2) 0.042(2) 0.001(2) C7 0.068(2) 0.090(3) 0.125(4) -0.022(3) 0.041(3) -0.021(2) C8 0.064(2) 0.070(2) 0.095(3) -0.025(2) 0.024(2) -0.0132(18) C9 0.071(2) 0.0494(17) 0.0415(15) -0.0046(13) 0.0156(14) 0.0009(15) C10 0.095(3) 0.058(2) 0.101(3) -0.007(2) 0.046(2) 0.010(2) C11 0.090(3) 0.092(3) 0.091(3) -0.010(2) 0.052(2) 0.007(2) C12 0.113(3) 0.087(3) 0.078(3) 0.014(2) 0.057(3) 0.011(3) C13 0.096(3) 0.065(2) 0.060(2) 0.0129(17) 0.038(2) 0.0151(19) C14 0.067(2) 0.072(2) 0.0566(19) 0.0099(16) 0.0228(16) 0.0129(17) C15 0.0567(18) 0.068(2) 0.0531(17) 0.0133(16) 0.0245(15) 0.0166(16) C16 0.066(2) 0.086(3) 0.079(2) 0.011(2) 0.0206(19) -0.002(2) C17 0.067(2) 0.110(3) 0.084(3) 0.027(2) 0.042(2) 0.024(2) C18 0.089(3) 0.100(3) 0.072(2) 0.008(2) 0.045(2) 0.033(2) C19 0.074(2) 0.072(2) 0.0588(19) -0.0004(17) 0.0224(17) 0.0123(18) _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 Mn1 O3W 2.145(3) . ? Mn1 O2W 2.160(3) . ? Mn1 N1 2.207(3) . ? Mn1 N1 2.207(3) 2_556 ? Mn1 O1W 2.217(2) 2_556 ? Mn1 O1W 2.217(2) . ? S1 C1 1.621(3) . ? N1 C1 1.147(4) . ? N2 C5 1.337(4) . ? N2 C4 1.342(4) . ? N3 C10 1.332(4) . ? N3 C9 1.345(4) . ? N4 C15 1.339(4) . ? N4 C16 1.341(5) . ? O1W H1W1 0.8456 . ? O1W H2W1 0.8045 . ? O2W H1W2 0.9492 . ? O3W H1W3 0.8114 . ? C2 C3 1.327(4) . ? C2 C4 1.463(4) . ? C2 H2 0.9300 . ? C3 C9 1.466(5) . ? C3 H3 0.9300 . ? C4 C8 1.383(5) . ? C5 C6 1.363(5) . ? C5 H5 0.9300 . ? C6 C7 1.359(6) . ? C6 H6 0.9300 . ? C7 C8 1.368(6) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C9 C13 1.379(5) . ? C10 C11 1.366(5) . ? C10 H10 0.9300 . ? C11 C12 1.365(6) . ? C11 H11 0.9300 . ? C12 C13 1.371(6) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C14 1.287(6) 3_566 ? C14 C15 1.479(5) . ? C14 H14 0.9300 . ? C15 C19 1.390(4) . ? C16 C17 1.376(6) . ? C16 H16 0.9300 . ? C17 C18 1.362(6) . ? C17 H17 0.9300 . ? C18 C19 1.374(5) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 C20 1.321(13) 3_556 ? C20 C21 1.415(8) . ? C20 H20 0.9300 . ? C21 N5 1.3900 . ? C21 C25 1.3900 . ? N5 C22 1.3900 . ? C22 C23 1.3900 . ? C22 H22 0.9300 . ? C23 C24 1.3900 . ? C23 H23 0.9300 . ? C24 C25 1.3900 . ? C24 H24 0.9300 . ? C25 H25 0.9300 . ? C20A C20A 1.264(16) 3_556 ? C20A C21A 1.449(10) . ? C20A H20A 0.9300 . ? C21A N5A 1.3900 . ? C21A C25A 1.3900 . ? N5A C22A 1.3900 . ? C22A C23A 1.3900 . ? C22A H22A 0.9300 . ? C23A C24A 1.3900 . ? C23A H23A 0.9300 . ? C24A C25A 1.3900 . ? C24A H24A 0.9300 . ? C25A H25A 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 O3W Mn1 O2W 180.000(1) . . ? O3W Mn1 N1 91.17(7) . . ? O2W Mn1 N1 88.83(7) . . ? O3W Mn1 N1 91.17(7) . 2_556 ? O2W Mn1 N1 88.83(7) . 2_556 ? N1 Mn1 N1 177.67(14) . 2_556 ? O3W Mn1 O1W 90.81(5) . 2_556 ? O2W Mn1 O1W 89.19(5) . 2_556 ? N1 Mn1 O1W 87.51(11) . 2_556 ? N1 Mn1 O1W 92.46(11) 2_556 2_556 ? O3W Mn1 O1W 90.81(5) . . ? O2W Mn1 O1W 89.19(5) . . ? N1 Mn1 O1W 92.46(11) . . ? N1 Mn1 O1W 87.51(11) 2_556 . ? O1W Mn1 O1W 178.38(11) 2_556 . ? C1 N1 Mn1 156.8(3) . . ? C5 N2 C4 117.9(3) . . ? C10 N3 C9 117.7(3) . . ? C15 N4 C16 117.4(3) . . ? Mn1 O1W H1W1 121.2 . . ? Mn1 O1W H2W1 122.4 . . ? H1W1 O1W H2W1 109.3 . . ? Mn1 O2W H1W2 130.0 . . ? Mn1 O3W H1W3 124.1 . . ? N1 C1 S1 179.9(3) . . ? C3 C2 C4 124.1(3) . . ? C3 C2 H2 118.0 . . ? C4 C2 H2 118.0 . . ? C2 C3 C9 124.9(3) . . ? C2 C3 H3 117.5 . . ? C9 C3 H3 117.5 . . ? N2 C4 C8 121.2(3) . . ? N2 C4 C2 115.3(3) . . ? C8 C4 C2 123.5(3) . . ? N2 C5 C6 123.5(3) . . ? N2 C5 H5 118.2 . . ? C6 C5 H5 118.2 . . ? C7 C6 C5 118.3(4) . . ? C7 C6 H6 120.8 . . ? C5 C6 H6 120.8 . . ? C6 C7 C8 119.7(4) . . ? C6 C7 H7 120.1 . . ? C8 C7 H7 120.1 . . ? C7 C8 C4 119.3(3) . . ? C7 C8 H8 120.4 . . ? C4 C8 H8 120.4 . . ? N3 C9 C13 121.2(3) . . ? N3 C9 C3 115.6(3) . . ? C13 C9 C3 123.3(3) . . ? N3 C10 C11 123.8(4) . . ? N3 C10 H10 118.1 . . ? C11 C10 H10 118.1 . . ? C12 C11 C10 118.6(4) . . ? C12 C11 H11 120.7 . . ? C10 C11 H11 120.7 . . ? C11 C12 C13 118.6(4) . . ? C11 C12 H12 120.7 . . ? C13 C12 H12 120.7 . . ? C12 C13 C9 120.1(3) . . ? C12 C13 H13 119.9 . . ? C9 C13 H13 119.9 . . ? C14 C14 C15 124.7(5) 3_566 . ? C14 C14 H14 117.7 3_566 . ? C15 C14 H14 117.7 . . ? N4 C15 C19 121.6(3) . . ? N4 C15 C14 120.5(3) . . ? C19 C15 C14 118.0(3) . . ? N4 C16 C17 123.7(4) . . ? N4 C16 H16 118.1 . . ? C17 C16 H16 118.1 . . ? C18 C17 C16 118.7(4) . . ? C18 C17 H17 120.7 . . ? C16 C17 H17 120.7 . . ? C17 C18 C19 118.8(4) . . ? C17 C18 H18 120.6 . . ? C19 C18 H18 120.6 . . ? C18 C19 C15 119.8(4) . . ? C18 C19 H19 120.1 . . ? C15 C19 H19 120.1 . . ? C20 C20 C21 126.3(10) 3_556 . ? C20 C20 H20 116.8 3_556 . ? C21 C20 H20 116.8 . . ? N5 C21 C25 120.0 . . ? N5 C21 C20 118.9(6) . . ? C25 C21 C20 121.0(6) . . ? C21 N5 C22 120.0 . . ? C23 C22 N5 120.0 . . ? C23 C22 H22 120.0 . . ? N5 C22 H22 120.0 . . ? C24 C23 C22 120.0 . . ? C24 C23 H23 120.0 . . ? C22 C23 H23 120.0 . . ? C23 C24 C25 120.0 . . ? C23 C24 H24 120.0 . . ? C25 C24 H24 120.0 . . ? C24 C25 C21 120.0 . . ? C24 C25 H25 120.0 . . ? C21 C25 H25 120.0 . . ? C20A C20A C21A 125.6(12) 3_556 . ? C20A C20A H20A 117.2 3_556 . ? C21A C20A H20A 117.2 . . ? N5A C21A C25A 120.0 . . ? N5A C21A C20A 116.8(7) . . ? C25A C21A C20A 123.1(8) . . ? C21A N5A C22A 120.0 . . ? C23A C22A N5A 120.0 . . ? C23A C22A H22A 120.0 . . ? N5A C22A H22A 120.0 . . ? C22A C23A C24A 120.0 . . ? C22A C23A H23A 120.0 . . ? C24A C23A H23A 120.0 . . ? C25A C24A C23A 120.0 . . ? C25A C24A H24A 120.0 . . ? C23A C24A H24A 120.0 . . ? C24A C25A C21A 120.0 . . ? C24A C25A H25A 120.0 . . ? C21A C25A H25A 120.0 . . ? _diffrn_measured_fraction_theta_max 0.844 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.404 _refine_diff_density_min -0.286 _refine_diff_density_rms 0.046 data_shelxle _database_code_depnum_ccdc_archive 'CCDC 606785' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Compound-Mn ; _chemical_name_common Compound-Mn _chemical_melting_point ? _chemical_formula_moiety '4(C12 H10 N2), C2 H8 Mn N2 O4 S2' _chemical_formula_sum 'C50 H48 Mn N10 O4 S2' _chemical_formula_weight 972.04 _chemical_compound_source Synthesis 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' Mn Mn 0.3368 0.7283 '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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.6800(14) _cell_length_b 10.1327(13) _cell_length_c 23.011(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.672(4) _cell_angle_gamma 90.00 _cell_volume 2487.4(6) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 3118 _cell_measurement_theta_min 1.7718 _cell_measurement_theta_max 27.8684 _exptl_crystal_description Plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.298 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1014 _exptl_absorpt_coefficient_mu 0.403 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.838 _exptl_absorpt_correction_T_max 0.930 _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku AFC7S Mercury' _diffrn_measurement_method \w _diffrn_radiation_detector CCD _diffrn_measurement_device ; Mercury (2x2 bin mode) ; _diffrn_detector_area_resol_mean 14.6306 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26596 _diffrn_reflns_av_R_equivalents 0.0353 _diffrn_reflns_av_sigmaI/netI 0.0304 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 28.11 _reflns_number_total 4752 _reflns_number_gt 3499 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_cell_refinement 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_data_reduction 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_structure_solution 'SHELXLTL-NT V5.1 (Bruker AXS, 1998)' _computing_structure_refinement 'SHELXLTL-NT V5.1 (Bruker AXS, 1998)' _computing_molecular_graphics ; SHELXLTL-NT V5.1 (Bruker AXS, 1998) and DIAMOND (Brandenburg, 1998) ; _computing_publication_material ; SHELXLTL-NT V5.1 (Bruker AXS, 1998) and PLATON (Spek, 2003). ; _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^)+(0.0892P)^2^+2.3075P] 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 4752 _refine_ls_number_parameters 242 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0937 _refine_ls_R_factor_gt 0.0684 _refine_ls_wR_factor_ref 0.1934 _refine_ls_wR_factor_gt 0.1719 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.048 _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 Mn1 Mn 0.0000 0.5000 0.5000 0.0472(2) Uani 1 2 d S . . S1 S -0.06340(14) 0.44511(14) 0.70967(4) 0.0914(4) Uani 1 1 d . . . N1 N -0.0330(3) 0.4559(3) 0.59056(13) 0.0638(8) Uani 1 1 d . . . O1W O 0.1595(2) 0.3651(2) 0.49998(10) 0.0603(6) Uani 1 1 d . . . H1W1 H 0.1886 0.3249 0.5301 0.072 Uiso 1 1 d R . . H2W1 H 0.2165 0.3770 0.4759 0.072 Uiso 1 1 d R . . O2W O 0.1303(2) 0.6577(2) 0.53258(11) 0.0625(7) Uani 1 1 d . . . H1W2 H 0.1852 0.6941 0.5123 0.075 Uiso 1 1 d R . . H2W2 H 0.0982 0.7216 0.5506 0.075 Uiso 1 1 d R . . C1 C -0.0451(4) 0.4514(4) 0.64003(15) 0.0563(9) Uani 1 1 d . . . C2 C 0.3055(7) 0.9896(8) 0.5566(3) 0.0660(18) Uiso 0.55 1 d P A 1 H2 H 0.3046 0.8995 0.5644 0.079 Uiso 0.55 1 calc PR A 1 C3 C 0.3182(7) 1.0227(9) 0.5043(4) 0.0672(19) Uiso 0.55 1 d P A 1 H3 H 0.3203 1.1127 0.4965 0.081 Uiso 0.55 1 calc PR A 1 C4 C 0.2921(5) 1.0773(6) 0.6064(2) 0.0630(19) Uiso 0.55 1 d PG A 1 N2 N 0.2655(5) 1.2092(6) 0.59460(18) 0.0637(16) Uiso 0.55 1 d PG A 1 C5 C 0.2553(7) 1.2983(4) 0.6400(3) 0.070(2) Uiso 0.55 1 d PG A 1 H5 H 0.2375 1.3865 0.6321 0.084 Uiso 0.55 1 calc PR A 1 C6 C 0.2718(9) 1.2557(6) 0.6973(2) 0.083(3) Uiso 0.55 1 d PG A 1 H6 H 0.2650 1.3153 0.7277 0.100 Uiso 0.55 1 calc PR A 1 C7 C 0.2984(9) 1.1238(7) 0.70911(17) 0.077(4) Uiso 0.55 1 d PG A 1 H7 H 0.3094 1.0953 0.7474 0.093 Uiso 0.55 1 calc PR A 1 C8 C 0.3086(7) 1.0347(5) 0.6637(3) 0.078(3) Uiso 0.55 1 d PG A 1 H8 H 0.3264 0.9464 0.6716 0.093 Uiso 0.55 1 calc PR A 1 C9 C 0.3298(6) 0.9357(5) 0.4557(2) 0.061(2) Uiso 0.55 1 d PG A 1 N3 N 0.3011(6) 0.8031(6) 0.46290(18) 0.058(2) Uiso 0.55 1 d PG A 1 C10 C 0.3092(6) 0.7160(4) 0.4166(3) 0.060(2) Uiso 0.55 1 d PG A 1 H10 H 0.2900 0.6273 0.4214 0.072 Uiso 0.55 1 calc PR A 1 C11 C 0.3461(6) 0.7615(6) 0.3630(2) 0.073(2) Uiso 0.55 1 d PG A 1 H11 H 0.3515 0.7032 0.3320 0.087 Uiso 0.55 1 calc PR A 1 C12 C 0.3748(6) 0.8941(7) 0.3558(2) 0.077(2) Uiso 0.55 1 d PG A 1 H12 H 0.3995 0.9245 0.3199 0.092 Uiso 0.55 1 calc PR A 1 C13 C 0.3667(6) 0.9812(4) 0.4021(3) 0.069(2) Uiso 0.55 1 d PG A 1 H13 H 0.3859 1.0700 0.3973 0.083 Uiso 0.55 1 calc PR A 1 C2A C 0.3192(7) 1.0851(8) 0.5419(3) 0.0535(18) Uiso 0.45 1 d P B 2 H2A H 0.3286 1.1486 0.5132 0.064 Uiso 0.45 1 calc PR B 2 C3A C 0.3224(7) 0.9587(9) 0.5247(4) 0.0536(18) Uiso 0.45 1 d P B 2 H3A H 0.3180 0.8954 0.5538 0.064 Uiso 0.45 1 calc PR B 2 C4A C 0.3029(6) 1.1322(7) 0.5991(2) 0.0482(17) Uiso 0.45 1 d PG B 2 N2A N 0.2654(6) 1.2629(7) 0.6040(2) 0.0601(19) Uiso 0.45 1 d PG B 2 C5A C 0.2468(8) 1.3167(5) 0.6585(3) 0.084(3) Uiso 0.45 1 d PG B 2 H5A H 0.2217 1.4041 0.6617 0.100 Uiso 0.45 1 calc PR B 2 C6A C 0.2657(11) 1.2397(8) 0.7081(2) 0.077(4) Uiso 0.45 1 d PG B 2 H6A H 0.2533 1.2756 0.7446 0.093 Uiso 0.45 1 calc PR B 2 C7A C 0.3033(11) 1.1089(8) 0.7032(2) 0.089(6) Uiso 0.45 1 d PG B 2 H7A H 0.3159 1.0574 0.7364 0.107 Uiso 0.45 1 calc PR B 2 C8A C 0.3218(8) 1.0552(5) 0.6487(3) 0.068(3) Uiso 0.45 1 d PG B 2 H8A H 0.3469 0.9677 0.6455 0.081 Uiso 0.45 1 calc PR B 2 C9A C 0.3318(7) 0.9105(7) 0.4667(2) 0.052(2) Uiso 0.45 1 d PG B 2 N3A N 0.3016(7) 0.7793(6) 0.4552(3) 0.062(3) Uiso 0.45 1 d PG B 2 C10A C 0.3098(7) 0.7293(5) 0.3993(3) 0.070(3) Uiso 0.45 1 d PG B 2 H10A H 0.2897 0.6415 0.3916 0.084 Uiso 0.45 1 calc PR B 2 C11A C 0.3482(7) 0.8105(8) 0.3548(2) 0.063(2) Uiso 0.45 1 d PG B 2 H11A H 0.3536 0.7770 0.3174 0.076 Uiso 0.45 1 calc PR B 2 C12A C 0.3783(7) 0.9417(7) 0.3662(3) 0.064(2) Uiso 0.45 1 d PG B 2 H12A H 0.4040 0.9960 0.3364 0.076 Uiso 0.45 1 calc PR B 2 C13A C 0.3701(7) 0.9917(4) 0.4222(3) 0.063(3) Uiso 0.45 1 d PG B 2 H13A H 0.3903 1.0795 0.4298 0.076 Uiso 0.45 1 calc PR B 2 C20 C 0.0001(4) 1.0356(4) 0.52348(14) 0.0902(14) Uani 1 1 d D . . H20 H 0.0028 1.1268 0.5191 0.108 Uiso 1 1 calc R . . C21 C -0.0036(4) 0.9837(4) 0.58298(15) 0.0629(10) Uani 1 1 d D . . C22 C 0.0125(5) 0.8249(5) 0.6532(2) 0.0848(13) Uani 1 1 d . . . H22 H 0.0291 0.7380 0.6639 0.102 Uiso 1 1 calc R . . C23 C -0.0190(5) 0.9130(6) 0.6954(2) 0.0945(16) Uani 1 1 d . . . H23 H -0.0260 0.8860 0.7337 0.113 Uiso 1 1 calc R . . C24 C -0.0398(5) 1.0411(6) 0.6797(2) 0.0920(15) Uani 1 1 d . . . H24 H -0.0596 1.1032 0.7075 0.110 Uiso 1 1 calc R . . C25 C -0.0317(4) 1.0770(5) 0.6241(2) 0.0769(12) Uani 1 1 d . . . H25 H -0.0450 1.1645 0.6132 0.092 Uiso 1 1 calc R . . N5 N 0.0203(3) 0.8585(4) 0.59770(15) 0.0711(9) Uani 1 1 d . . . N4 N 0.3572(3) 0.3855(3) 0.42137(12) 0.0560(7) Uani 1 1 d . . . C14 C 0.5326(4) 0.4739(4) 0.47931(15) 0.0577(9) Uani 1 1 d . . . H14 H 0.6195 0.4796 0.4838 0.069 Uiso 1 1 calc R . . C15 C 0.4812(4) 0.4079(3) 0.42696(14) 0.0528(8) Uani 1 1 d . . . C17 C 0.3834(5) 0.2967(4) 0.32656(16) 0.0712(11) Uani 1 1 d . . . H17 H 0.3471 0.2611 0.2925 0.085 Uiso 1 1 calc R . . C18 C 0.5095(5) 0.3152(4) 0.33288(16) 0.0744(12) Uani 1 1 d . . . H18 H 0.5613 0.2900 0.3035 0.089 Uiso 1 1 calc R . . C19 C 0.5598(4) 0.3715(4) 0.38334(16) 0.0665(10) Uani 1 1 d . . . H19 H 0.6458 0.3850 0.3881 0.080 Uiso 1 1 calc R . . C16 C 0.3112(4) 0.3320(4) 0.37195(16) 0.0656(10) Uani 1 1 d . . . H16 H 0.2252 0.3178 0.3680 0.079 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 Mn1 0.0554(5) 0.0520(4) 0.0348(4) 0.0042(3) 0.0068(3) -0.0014(3) S1 0.1343(12) 0.1048(9) 0.0358(6) 0.0040(5) 0.0113(6) -0.0093(8) N1 0.077(2) 0.073(2) 0.0422(18) 0.0086(14) 0.0111(14) -0.0015(16) O1W 0.0629(16) 0.0692(16) 0.0491(14) 0.0093(11) 0.0082(11) 0.0075(12) O2W 0.0658(16) 0.0587(15) 0.0640(16) -0.0045(12) 0.0122(12) -0.0083(12) C1 0.071(2) 0.057(2) 0.041(2) 0.0049(15) 0.0054(16) -0.0049(17) C20 0.060(3) 0.108(4) 0.102(4) -0.016(3) -0.005(3) 0.004(2) C21 0.050(2) 0.086(3) 0.052(2) 0.0018(18) -0.0052(16) 0.0011(18) C22 0.094(3) 0.073(3) 0.087(3) 0.013(2) 0.002(3) -0.009(2) C23 0.093(4) 0.137(5) 0.053(3) 0.005(3) 0.004(2) -0.002(3) C24 0.086(3) 0.121(4) 0.068(3) -0.032(3) -0.003(2) 0.019(3) C25 0.072(3) 0.076(3) 0.081(3) -0.005(2) -0.012(2) 0.014(2) N5 0.071(2) 0.076(2) 0.066(2) -0.0182(17) 0.0001(17) -0.0085(17) N4 0.064(2) 0.0606(18) 0.0438(15) -0.0058(12) 0.0037(13) 0.0065(14) C14 0.058(2) 0.063(2) 0.051(2) -0.0032(15) -0.0008(16) 0.0048(16) C15 0.061(2) 0.0525(19) 0.0452(18) -0.0003(14) 0.0047(15) 0.0080(15) C17 0.096(3) 0.071(3) 0.046(2) -0.0081(17) -0.001(2) 0.004(2) C18 0.097(3) 0.081(3) 0.047(2) -0.0068(18) 0.021(2) 0.013(2) C19 0.063(2) 0.080(3) 0.057(2) -0.0043(18) 0.0136(18) 0.0051(19) C16 0.068(3) 0.069(2) 0.058(2) -0.0067(18) -0.0054(18) -0.0003(19) _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 Mn1 N1 2.176(3) 3_566 ? Mn1 N1 2.176(3) . ? Mn1 O1W 2.184(2) 3_566 ? Mn1 O1W 2.184(2) . ? Mn1 O2W 2.226(2) 3_566 ? Mn1 O2W 2.226(2) . ? S1 C1 1.625(4) . ? N1 C1 1.153(4) . ? O1W H1W1 0.8499 . ? O1W H2W1 0.8500 . ? O2W H1W2 0.8502 . ? O2W H2W2 0.8498 . ? C2 C3 1.264(11) . ? C2 C4 1.462(9) . ? C2 H2 0.9300 . ? C3 C9 1.433(9) . ? C3 H3 0.9300 . ? C4 N2 1.3900 . ? C4 C8 1.3900 . ? N2 C5 1.3900 . ? C5 C6 1.3900 . ? C5 H5 0.9300 . ? C6 C7 1.3900 . ? C6 H6 0.9300 . ? C7 C8 1.3900 . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C9 N3 1.3900 . ? C9 C13 1.3900 . ? N3 C10 1.3900 . ? C10 C11 1.3900 . ? C10 H10 0.9300 . ? C11 C12 1.3900 . ? C11 H11 0.9300 . ? C12 C13 1.3900 . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C2A C3A 1.341(12) . ? C2A C4A 1.419(9) . ? C2A H2A 0.9300 . ? C3A C9A 1.430(10) . ? C3A H3A 0.9300 . ? C4A N2A 1.3900 . ? C4A C8A 1.3900 . ? N2A C5A 1.3900 . ? C5A C6A 1.3900 . ? C5A H5A 0.9300 . ? C6A C7A 1.3900 . ? C6A H6A 0.9300 . ? C7A C8A 1.3900 . ? C7A H7A 0.9300 . ? C8A H8A 0.9300 . ? C9A N3A 1.3900 . ? C9A C13A 1.3900 . ? N3A C10A 1.3900 . ? C10A C11A 1.3900 . ? C10A H10A 0.9300 . ? C11A C12A 1.3900 . ? C11A H11A 0.9300 . ? C12A C13A 1.3900 . ? C12A H12A 0.9300 . ? C13A H13A 0.9300 . ? C20 C20 1.299(4) 3_576 ? C20 C21 1.469(4) . ? C20 H20 0.9300 . ? C21 N5 1.335(5) . ? C21 C25 1.381(6) . ? C22 N5 1.328(6) . ? C22 C23 1.372(7) . ? C22 H22 0.9300 . ? C23 C24 1.362(8) . ? C23 H23 0.9300 . ? C24 C25 1.337(7) . ? C24 H24 0.9300 . ? C25 H25 0.9300 . ? N4 C16 1.333(5) . ? N4 C15 1.343(5) . ? C14 C14 1.317(7) 3_666 ? C14 C15 1.463(5) . ? C14 H14 0.9300 . ? C15 C19 1.388(5) . ? C17 C18 1.361(6) . ? C17 C16 1.375(6) . ? C17 H17 0.9300 . ? C18 C19 1.380(6) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C16 H16 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 N1 Mn1 N1 180.000(1) 3_566 . ? N1 Mn1 O1W 91.88(11) 3_566 3_566 ? N1 Mn1 O1W 88.12(11) . 3_566 ? N1 Mn1 O1W 88.12(11) 3_566 . ? N1 Mn1 O1W 91.88(11) . . ? O1W Mn1 O1W 180.000(1) 3_566 . ? N1 Mn1 O2W 87.23(11) 3_566 3_566 ? N1 Mn1 O2W 92.77(11) . 3_566 ? O1W Mn1 O2W 88.53(10) 3_566 3_566 ? O1W Mn1 O2W 91.47(10) . 3_566 ? N1 Mn1 O2W 92.77(11) 3_566 . ? N1 Mn1 O2W 87.23(11) . . ? O1W Mn1 O2W 91.47(10) 3_566 . ? O1W Mn1 O2W 88.53(10) . . ? O2W Mn1 O2W 180.00(15) 3_566 . ? C1 N1 Mn1 169.9(3) . . ? Mn1 O1W H1W1 123.7 . . ? Mn1 O1W H2W1 119.6 . . ? H1W1 O1W H2W1 110.7 . . ? Mn1 O2W H1W2 124.3 . . ? Mn1 O2W H2W2 116.9 . . ? H1W2 O2W H2W2 103.9 . . ? N1 C1 S1 179.6(4) . . ? C3 C2 C4 127.2(8) . . ? C3 C2 H2 116.4 . . ? C4 C2 H2 116.4 . . ? C2 C3 C9 126.7(9) . . ? C2 C3 H3 116.6 . . ? C9 C3 H3 116.6 . . ? N2 C4 C8 120.0 . . ? N2 C4 C2 117.3(5) . . ? C8 C4 C2 122.7(5) . . ? C4 N2 C5 120.0 . . ? C6 C5 N2 120.0 . . ? C6 C5 H5 120.0 . . ? N2 C5 H5 120.0 . . ? C5 C6 C7 120.0 . . ? C5 C6 H6 120.0 . . ? C7 C6 H6 120.0 . . ? C8 C7 C6 120.0 . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C7 C8 C4 120.0 . . ? C7 C8 H8 120.0 . . ? C4 C8 H8 120.0 . . ? N3 C9 C13 120.0 . . ? N3 C9 C3 118.3(6) . . ? C13 C9 C3 121.7(6) . . ? C9 N3 C10 120.0 . . ? C11 C10 N3 120.0 . . ? C11 C10 H10 120.0 . . ? N3 C10 H10 120.0 . . ? C10 C11 C12 120.0 . . ? C10 C11 H11 120.0 . . ? C12 C11 H11 120.0 . . ? C13 C12 C11 120.0 . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C12 C13 C9 120.0 . . ? C12 C13 H13 120.0 . . ? C9 C13 H13 120.0 . . ? C3A C2A C4A 126.9(8) . . ? C3A C2A H2A 116.6 . . ? C4A C2A H2A 116.6 . . ? C2A C3A C9A 127.2(9) . . ? C2A C3A H3A 116.4 . . ? C9A C3A H3A 116.4 . . ? N2A C4A C8A 120.0 . . ? N2A C4A C2A 116.3(6) . . ? C8A C4A C2A 123.7(6) . . ? C4A N2A C5A 120.0 . . ? C6A C5A N2A 120.0 . . ? C6A C5A H5A 120.0 . . ? N2A C5A H5A 120.0 . . ? C5A C6A C7A 120.0 . . ? C5A C6A H6A 120.0 . . ? C7A C6A H6A 120.0 . . ? C8A C7A C6A 120.0 . . ? C8A C7A H7A 120.0 . . ? C6A C7A H7A 120.0 . . ? C7A C8A C4A 120.0 . . ? C7A C8A H8A 120.0 . . ? C4A C8A H8A 120.0 . . ? N3A C9A C13A 120.0 . . ? N3A C9A C3A 118.6(7) . . ? C13A C9A C3A 121.4(7) . . ? C9A N3A C10A 120.0 . . ? C11A C10A N3A 120.0 . . ? C11A C10A H10A 120.0 . . ? N3A C10A H10A 120.0 . . ? C10A C11A C12A 120.0 . . ? C10A C11A H11A 120.0 . . ? C12A C11A H11A 120.0 . . ? C13A C12A C11A 120.0 . . ? C13A C12A H12A 120.0 . . ? C11A C12A H12A 120.0 . . ? C12A C13A C9A 120.0 . . ? C12A C13A H13A 120.0 . . ? C9A C13A H13A 120.0 . . ? C20 C20 C21 125.2(6) 3_576 . ? C20 C20 H20 117.4 3_576 . ? C21 C20 H20 117.4 . . ? N5 C21 C25 121.5(4) . . ? N5 C21 C20 124.3(4) . . ? C25 C21 C20 114.1(4) . . ? N5 C22 C23 122.9(5) . . ? N5 C22 H22 118.6 . . ? C23 C22 H22 118.6 . . ? C24 C23 C22 118.3(5) . . ? C24 C23 H23 120.9 . . ? C22 C23 H23 120.9 . . ? C25 C24 C23 119.8(5) . . ? C25 C24 H24 120.1 . . ? C23 C24 H24 120.1 . . ? C24 C25 C21 119.6(4) . . ? C24 C25 H25 120.2 . . ? C21 C25 H25 120.2 . . ? C22 N5 C21 117.9(4) . . ? C16 N4 C15 118.2(3) . . ? C14 C14 C15 126.0(5) 3_666 . ? C14 C14 H14 117.0 3_666 . ? C15 C14 H14 117.0 . . ? N4 C15 C19 120.8(3) . . ? N4 C15 C14 119.1(3) . . ? C19 C15 C14 120.0(4) . . ? C18 C17 C16 118.1(4) . . ? C18 C17 H17 121.0 . . ? C16 C17 H17 121.0 . . ? C17 C18 C19 119.4(4) . . ? C17 C18 H18 120.3 . . ? C19 C18 H18 120.3 . . ? C18 C19 C15 119.6(4) . . ? C18 C19 H19 120.2 . . ? C15 C19 H19 120.2 . . ? N4 C16 C17 123.8(4) . . ? N4 C16 H16 118.1 . . ? C17 C16 H16 118.1 . . ? _diffrn_measured_fraction_theta_max 0.781 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 1.002 _refine_diff_density_min -0.495 _refine_diff_density_rms 0.061 #_vrf_PLAT201_shelxle #; #PROBLEM: Isotropic non-H Atoms in Main Residue(s) 14 #RESPONSE: these atoms correspond to one disordered #molecule and its anisotropic refinement is unstable #; # end Validation Reply Form #===END #CCDC 606785 (Compound-Co) data_shelxlps _database_code_depnum_ccdc_archive 'CCDC 606786' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Compound-Co ; _chemical_name_common Compound-Co _chemical_melting_point ? _chemical_formula_moiety '4(C12 H10 N2), C2 H8 Co N2 O4 S2' _chemical_formula_sum 'C50 H48 Co N10 O4 S2' _chemical_formula_weight 976.03 _chemical_compound_source Synthesis 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' Co Co 0.3494 0.9721 '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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.6357(10) _cell_length_b 10.1079(9) _cell_length_c 22.888(2) _cell_angle_alpha 90.00 _cell_angle_beta 92.203(3) _cell_angle_gamma 90.00 _cell_volume 2458.7(4) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 3112 _cell_measurement_theta_min 1.78 _cell_measurement_theta_max 28.18 _exptl_crystal_description Plate _exptl_crystal_colour pink _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.318 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1018 _exptl_absorpt_coefficient_mu 0.488 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.840 _exptl_absorpt_correction_T_max 0.910 _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku AFC7S Mercury' _diffrn_measurement_method \w _diffrn_radiation_detector CCD _diffrn_measurement_device ; Mercury (2x2 bin mode) ; _diffrn_detector_area_resol_mean 14.6306 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27138 _diffrn_reflns_av_R_equivalents 0.0400 _diffrn_reflns_av_sigmaI/netI 0.0397 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 28.18 _reflns_number_total 4865 _reflns_number_gt 3538 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_cell_refinement 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_data_reduction 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_structure_solution 'SHELXLTL-NT V5.1 (Bruker AXS, 1998)' _computing_structure_refinement 'SHELXLTL-NT V5.1 (Bruker AXS, 1998)' _computing_molecular_graphics ; SHELXLTL-NT V5.1 (Bruker AXS, 1998) and DIAMOND (Brandenburg, 1998) ; _computing_publication_material ; SHELXLTL-NT V5.1 (Bruker AXS, 1998) and PLATON (Spek, 2003). ; _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^)+(0.0873P)^2^+2.8960P] 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 4865 _refine_ls_number_parameters 242 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0977 _refine_ls_R_factor_gt 0.0684 _refine_ls_wR_factor_ref 0.1938 _refine_ls_wR_factor_gt 0.1715 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.041 _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 Co1 Co 0.0000 0.5000 0.5000 0.0443(2) Uani 1 2 d S . . S1 S -0.06408(15) 0.44637(15) 0.70756(4) 0.0838(4) Uani 1 1 d . . . N1 N -0.0341(3) 0.4581(3) 0.58741(13) 0.0564(8) Uani 1 1 d . . . O1W O 0.1255(2) 0.6497(3) 0.53114(11) 0.0584(7) Uani 1 1 d . . . H2W1 H 0.1706 0.6919 0.5076 0.070 Uiso 1 1 d R . . H1W1 H 0.0765 0.7076 0.5446 0.070 Uiso 1 1 d R . . O2W O 0.1516(2) 0.3685(3) 0.49978(11) 0.0558(7) Uani 1 1 d . . . H1W2 H 0.1788 0.3287 0.5305 0.067 Uiso 1 1 d R . . H2W2 H 0.2120 0.3824 0.4773 0.067 Uiso 1 1 d R . . C1 C -0.0460(4) 0.4532(4) 0.63739(16) 0.0513(9) Uani 1 1 d . . . C2 C 0.3161(6) 0.0833(6) 0.5403(3) 0.0594(14) Uiso 0.70 1 d P A 1 H2 H 0.3245 0.1469 0.5114 0.071 Uiso 0.70 1 calc PR A 1 C3 C 0.3198(6) -0.0420(7) 0.5238(3) 0.0604(15) Uiso 0.70 1 d P A 1 H3 H 0.3159 -0.1056 0.5530 0.072 Uiso 0.70 1 calc PR A 1 C4 C 0.3003(4) 0.1299(5) 0.59816(15) 0.0527(13) Uiso 0.70 1 d PG A 1 N2 N 0.2626(4) 0.2612(5) 0.60173(16) 0.0609(14) Uiso 0.70 1 d PG A 1 C5 C 0.2451(5) 0.3186(3) 0.6560(2) 0.074(2) Uiso 0.70 1 d PG A 1 H5 H 0.2199 0.4065 0.6584 0.089 Uiso 0.70 1 calc PR A 1 C6 C 0.2653(7) 0.2447(5) 0.70671(15) 0.074(2) Uiso 0.70 1 d PG A 1 H6 H 0.2536 0.2831 0.7430 0.089 Uiso 0.70 1 calc PR A 1 C7 C 0.3029(7) 0.1133(5) 0.70313(17) 0.077(3) Uiso 0.70 1 d PG A 1 H7 H 0.3164 0.0639 0.7371 0.093 Uiso 0.70 1 calc PR A 1 C8 C 0.3204(5) 0.0559(3) 0.6489(2) 0.0686(18) Uiso 0.70 1 d PG A 1 H8 H 0.3456 -0.0319 0.6465 0.082 Uiso 0.70 1 calc PR A 1 C9 C 0.3293(5) -0.0890(5) 0.46539(15) 0.0515(17) Uiso 0.70 1 d PG A 1 N3 N 0.2990(5) -0.2211(4) 0.45567(18) 0.061(2) Uiso 0.70 1 d PG A 1 C10 C 0.3066(5) -0.2747(3) 0.4000(2) 0.070(2) Uiso 0.70 1 d PG A 1 H10 H 0.2863 -0.3632 0.3935 0.084 Uiso 0.70 1 calc PR A 1 C11 C 0.3445(5) -0.1962(6) 0.35403(15) 0.0685(18) Uiso 0.70 1 d PG A 1 H11 H 0.3496 -0.2321 0.3168 0.082 Uiso 0.70 1 calc PR A 1 C12 C 0.3749(5) -0.0641(5) 0.36375(18) 0.0674(18) Uiso 0.70 1 d PG A 1 H12 H 0.4003 -0.0116 0.3330 0.081 Uiso 0.70 1 calc PR A 1 C13 C 0.3673(5) -0.0105(3) 0.4194(2) 0.0623(18) Uiso 0.70 1 d PG A 1 H13 H 0.3876 0.0780 0.4259 0.075 Uiso 0.70 1 calc PR A 1 C2A C 0.3029(13) -0.0116(14) 0.5554(6) 0.057(3) Uiso 0.30 1 d P B 2 H2A H 0.3037 -0.1024 0.5619 0.068 Uiso 0.30 1 calc PR B 2 C3A C 0.3141(14) 0.0253(17) 0.5034(7) 0.065(4) Uiso 0.30 1 d P B 2 H3A H 0.3132 0.1158 0.4960 0.077 Uiso 0.30 1 calc PR B 2 C4A C 0.2882(11) 0.0746(11) 0.6081(5) 0.069(4) Uiso 0.30 1 d PG B 2 N2A N 0.2645(10) 0.2061(13) 0.5938(3) 0.058(3) Uiso 0.30 1 d PG B 2 C5A C 0.2579(12) 0.3005(8) 0.6377(5) 0.063(4) Uiso 0.30 1 d PG B 2 H5A H 0.2420 0.3885 0.6282 0.076 Uiso 0.30 1 calc PR B 2 C6A C 0.2750(16) 0.2634(11) 0.6960(4) 0.086(7) Uiso 0.30 1 d PG B 2 H6A H 0.2706 0.3265 0.7254 0.103 Uiso 0.30 1 calc PR B 2 C7A C 0.2988(16) 0.1318(13) 0.7103(3) 0.075(7) Uiso 0.30 1 d PG B 2 H7A H 0.3103 0.1070 0.7492 0.090 Uiso 0.30 1 calc PR B 2 C8A C 0.3054(14) 0.0374(9) 0.6663(6) 0.077(5) Uiso 0.30 1 d PG B 2 H8A H 0.3213 -0.0506 0.6759 0.092 Uiso 0.30 1 calc PR B 2 C9A C 0.3283(12) -0.0625(9) 0.4542(4) 0.066(5) Uiso 0.30 1 d PG B 2 N3A N 0.3018(11) -0.1953(11) 0.4636(3) 0.056(4) Uiso 0.30 1 d PG B 2 C10A C 0.3106(10) -0.2859(7) 0.4183(5) 0.047(3) Uiso 0.30 1 d PG B 2 H10A H 0.2929 -0.3747 0.4246 0.056 Uiso 0.30 1 calc PR B 2 C11A C 0.3460(11) -0.2437(11) 0.3635(4) 0.064(4) Uiso 0.30 1 d PG B 2 H11A H 0.3520 -0.3043 0.3332 0.077 Uiso 0.30 1 calc PR B 2 C12A C 0.3725(11) -0.1109(12) 0.3540(4) 0.067(4) Uiso 0.30 1 d PG B 2 H12A H 0.3962 -0.0827 0.3174 0.080 Uiso 0.30 1 calc PR B 2 C13A C 0.3637(11) -0.0203(7) 0.3994(6) 0.056(4) Uiso 0.30 1 d PG B 2 H13A H 0.3814 0.0685 0.3930 0.067 Uiso 0.30 1 calc PR B 2 C20 C -0.0001(5) -0.0331(6) 0.47579(15) 0.111(2) Uani 1 1 d D . . H20 H -0.0023 -0.1248 0.4790 0.133 Uiso 1 1 calc R . . C21 C 0.0028(4) 0.0213(5) 0.41657(18) 0.0640(11) Uani 1 1 d D . . N5 N -0.0218(4) 0.1457(4) 0.40150(17) 0.0721(10) Uani 1 1 d . . . C22 C -0.0151(5) 0.1771(5) 0.3456(3) 0.0857(15) Uani 1 1 d . . . H22 H -0.0323 0.2638 0.3343 0.103 Uiso 1 1 calc R . . C23 C 0.0161(5) 0.0871(7) 0.3033(2) 0.0928(17) Uani 1 1 d . . . H23 H 0.0228 0.1127 0.2645 0.111 Uiso 1 1 calc R . . C24 C 0.0367(5) -0.0408(6) 0.3202(2) 0.0897(16) Uani 1 1 d . . . H24 H 0.0555 -0.1045 0.2925 0.108 Uiso 1 1 calc R . . C25 C 0.0300(4) -0.0743(5) 0.3759(2) 0.0763(13) Uani 1 1 d . . . H25 H 0.0436 -0.1614 0.3875 0.092 Uiso 1 1 calc R . . C14 C 0.5325(4) 0.4732(4) 0.47936(17) 0.0596(10) Uani 1 1 d . . . H14 H 0.6197 0.4779 0.4835 0.071 Uiso 1 1 calc R . . C15 C 0.4795(4) 0.4062(4) 0.42687(16) 0.0530(9) Uani 1 1 d . . . C16 C 0.3094(4) 0.3300(4) 0.37238(18) 0.0642(11) Uani 1 1 d . . . H16 H 0.2231 0.3161 0.3685 0.077 Uiso 1 1 calc R . . C17 C 0.3828(5) 0.2929(4) 0.32688(18) 0.0691(12) Uani 1 1 d . . . H17 H 0.3469 0.2564 0.2929 0.083 Uiso 1 1 calc R . . C18 C 0.5093(5) 0.3111(5) 0.33303(18) 0.0731(13) Uani 1 1 d . . . H18 H 0.5615 0.2852 0.3034 0.088 Uiso 1 1 calc R . . C19 C 0.5598(4) 0.3682(4) 0.38352(18) 0.0669(11) Uani 1 1 d . . . H19 H 0.6462 0.3809 0.3884 0.080 Uiso 1 1 calc R . . N4 N 0.3552(3) 0.3847(3) 0.42162(13) 0.0553(8) Uani 1 1 d . . . 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 Co1 0.0525(4) 0.0488(4) 0.0321(4) 0.0038(3) 0.0067(3) 0.0002(3) S1 0.1212(12) 0.0976(9) 0.0333(6) 0.0047(5) 0.0115(6) -0.0075(8) N1 0.066(2) 0.064(2) 0.0395(18) 0.0063(14) 0.0086(15) -0.0009(16) O1W 0.0613(17) 0.0572(15) 0.0572(16) -0.0029(12) 0.0106(13) -0.0046(12) O2W 0.0610(17) 0.0615(16) 0.0453(14) 0.0084(11) 0.0079(12) 0.0095(12) C1 0.062(2) 0.053(2) 0.039(2) 0.0046(15) 0.0066(17) -0.0033(17) C20 0.054(3) 0.166(6) 0.113(5) -0.018(4) 0.003(3) 0.003(3) C21 0.047(2) 0.093(3) 0.051(2) 0.004(2) -0.0023(18) -0.003(2) N5 0.068(2) 0.079(3) 0.070(3) -0.021(2) 0.0001(19) -0.0066(19) C22 0.091(4) 0.069(3) 0.097(4) 0.014(3) 0.004(3) -0.010(3) C23 0.086(4) 0.142(6) 0.050(3) 0.009(3) 0.006(2) 0.001(4) C24 0.082(4) 0.117(5) 0.069(3) -0.031(3) -0.006(3) 0.020(3) C25 0.069(3) 0.073(3) 0.086(3) -0.002(3) -0.009(2) 0.012(2) C14 0.061(3) 0.064(3) 0.054(2) -0.0017(18) 0.0001(18) 0.0076(18) C15 0.063(3) 0.051(2) 0.045(2) 0.0007(15) 0.0033(17) 0.0054(17) C16 0.067(3) 0.068(3) 0.058(2) -0.0063(19) -0.001(2) 0.001(2) C17 0.090(4) 0.071(3) 0.046(2) -0.0075(19) -0.002(2) 0.004(2) C18 0.092(4) 0.081(3) 0.048(2) -0.006(2) 0.022(2) 0.012(3) C19 0.061(3) 0.079(3) 0.061(3) -0.003(2) 0.013(2) 0.003(2) N4 0.062(2) 0.0598(19) 0.0443(17) -0.0037(14) 0.0056(15) 0.0071(15) _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 Co1 O2W 2.089(2) . ? Co1 O2W 2.089(2) 3_566 ? Co1 N1 2.090(3) . ? Co1 N1 2.090(3) 3_566 ? Co1 O1W 2.123(3) . ? Co1 O1W 2.123(3) 3_566 ? S1 C1 1.626(4) . ? N1 C1 1.157(5) . ? O1W H2W1 0.8497 . ? O1W H1W1 0.8500 . ? O2W H1W2 0.8502 . ? O2W H2W2 0.8501 . ? C2 C3 1.323(9) . ? C2 C4 1.421(7) . ? C2 H2 0.9300 . ? C3 C9 1.425(7) . ? C3 H3 0.9300 . ? C4 N2 1.3900 . ? C4 C8 1.3900 . ? N2 C5 1.3900 . ? C5 C6 1.3900 . ? C5 H5 0.9300 . ? C6 C7 1.3900 . ? C6 H6 0.9300 . ? C7 C8 1.3900 . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C9 N3 1.3900 . ? C9 C13 1.3900 . ? N3 C10 1.3900 . ? C10 C11 1.3900 . ? C10 H10 0.9300 . ? C11 C12 1.3900 . ? C11 H11 0.9300 . ? C12 C13 1.3900 . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C2A C3A 1.26(2) . ? C2A C4A 1.501(17) . ? C2A H2A 0.9300 . ? C3A C9A 1.447(17) . ? C3A H3A 0.9300 . ? C4A N2A 1.3900 . ? C4A C8A 1.3900 . ? N2A C5A 1.3900 . ? C5A C6A 1.3900 . ? C5A H5A 0.9300 . ? C6A C7A 1.3900 . ? C6A H6A 0.9300 . ? C7A C8A 1.3900 . ? C7A H7A 0.9300 . ? C8A H8A 0.9300 . ? C9A N3A 1.3900 . ? C9A C13A 1.3900 . ? N3A C10A 1.3900 . ? C10A C11A 1.3900 . ? C10A H10A 0.9300 . ? C11A C12A 1.3900 . ? C11A H11A 0.9300 . ? C12A C13A 1.3900 . ? C12A H12A 0.9300 . ? C13A H13A 0.9300 . ? C20 C20 1.294(5) 3_556 ? C20 C21 1.464(4) . ? C20 H20 0.9300 . ? C21 N5 1.327(6) . ? C21 C25 1.380(7) . ? N5 C22 1.323(6) . ? C22 C23 1.378(8) . ? C22 H22 0.9300 . ? C23 C24 1.365(8) . ? C23 H23 0.9300 . ? C24 C25 1.324(7) . ? C24 H24 0.9300 . ? C25 H25 0.9300 . ? C14 C14 1.309(8) 3_666 ? C14 C15 1.472(5) . ? C14 H14 0.9300 . ? C15 N4 1.341(5) . ? C15 C19 1.388(6) . ? C16 N4 1.330(5) . ? C16 C17 1.378(6) . ? C16 H16 0.9300 . ? C17 C18 1.359(7) . ? C17 H17 0.9300 . ? C18 C19 1.382(6) . ? C18 H18 0.9300 . ? C19 H19 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 O2W Co1 O2W 180.000(1) . 3_566 ? O2W Co1 N1 92.05(11) . . ? O2W Co1 N1 87.95(11) 3_566 . ? O2W Co1 N1 87.95(11) . 3_566 ? O2W Co1 N1 92.05(11) 3_566 3_566 ? N1 Co1 N1 180.000(1) . 3_566 ? O2W Co1 O1W 88.77(10) . . ? O2W Co1 O1W 91.23(10) 3_566 . ? N1 Co1 O1W 87.33(12) . . ? N1 Co1 O1W 92.67(12) 3_566 . ? O2W Co1 O1W 91.23(10) . 3_566 ? O2W Co1 O1W 88.77(10) 3_566 3_566 ? N1 Co1 O1W 92.67(12) . 3_566 ? N1 Co1 O1W 87.33(12) 3_566 3_566 ? O1W Co1 O1W 180.0 . 3_566 ? C1 N1 Co1 169.9(3) . . ? Co1 O1W H2W1 120.5 . . ? Co1 O1W H1W1 103.1 . . ? H2W1 O1W H1W1 104.7 . . ? Co1 O2W H1W2 122.5 . . ? Co1 O2W H2W2 119.9 . . ? H1W2 O2W H2W2 109.7 . . ? N1 C1 S1 179.5(4) . . ? C3 C2 C4 126.2(6) . . ? C3 C2 H2 116.9 . . ? C4 C2 H2 116.9 . . ? C2 C3 C9 126.3(7) . . ? C2 C3 H3 116.9 . . ? C9 C3 H3 116.9 . . ? N2 C4 C8 120.0 . . ? N2 C4 C2 114.6(5) . . ? C8 C4 C2 125.4(5) . . ? C5 N2 C4 120.0 . . ? N2 C5 C6 120.0 . . ? N2 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C7 C6 C5 120.0 . . ? C7 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? C6 C7 C8 120.0 . . ? C6 C7 H7 120.0 . . ? C8 C7 H7 120.0 . . ? C7 C8 C4 120.0 . . ? C7 C8 H8 120.0 . . ? C4 C8 H8 120.0 . . ? N3 C9 C13 120.0 . . ? N3 C9 C3 116.5(5) . . ? C13 C9 C3 123.5(5) . . ? C9 N3 C10 120.0 . . ? C11 C10 N3 120.0 . . ? C11 C10 H10 120.0 . . ? N3 C10 H10 120.0 . . ? C12 C11 C10 120.0 . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C13 C12 C11 120.0 . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C12 C13 C9 120.0 . . ? C12 C13 H13 120.0 . . ? C9 C13 H13 120.0 . . ? C3A C2A C4A 127.3(15) . . ? C3A C2A H2A 116.4 . . ? C4A C2A H2A 116.4 . . ? C2A C3A C9A 124.9(16) . . ? C2A C3A H3A 117.6 . . ? C9A C3A H3A 117.6 . . ? N2A C4A C8A 120.0 . . ? N2A C4A C2A 112.9(11) . . ? C8A C4A C2A 126.9(10) . . ? C5A N2A C4A 120.0 . . ? C6A C5A N2A 120.0 . . ? C6A C5A H5A 120.0 . . ? N2A C5A H5A 120.0 . . ? C5A C6A C7A 120.0 . . ? C5A C6A H6A 120.0 . . ? C7A C6A H6A 120.0 . . ? C8A C7A C6A 120.0 . . ? C8A C7A H7A 120.0 . . ? C6A C7A H7A 120.0 . . ? C7A C8A C4A 120.0 . . ? C7A C8A H8A 120.0 . . ? C4A C8A H8A 120.0 . . ? N3A C9A C13A 120.0 . . ? N3A C9A C3A 116.3(11) . . ? C13A C9A C3A 123.7(11) . . ? C9A N3A C10A 120.0 . . ? C11A C10A N3A 120.0 . . ? C11A C10A H10A 120.0 . . ? N3A C10A H10A 120.0 . . ? C10A C11A C12A 120.0 . . ? C10A C11A H11A 120.0 . . ? C12A C11A H11A 120.0 . . ? C11A C12A C13A 120.0 . . ? C11A C12A H12A 120.0 . . ? C13A C12A H12A 120.0 . . ? C12A C13A C9A 120.0 . . ? C12A C13A H13A 120.0 . . ? C9A C13A H13A 120.0 . . ? C20 C20 C21 126.8(7) 3_556 . ? C20 C20 H20 116.6 3_556 . ? C21 C20 H20 116.6 . . ? N5 C21 C25 122.1(4) . . ? N5 C21 C20 125.8(4) . . ? C25 C21 C20 112.0(4) . . ? C22 N5 C21 117.5(4) . . ? N5 C22 C23 123.0(5) . . ? N5 C22 H22 118.5 . . ? C23 C22 H22 118.5 . . ? C24 C23 C22 117.8(5) . . ? C24 C23 H23 121.1 . . ? C22 C23 H23 121.1 . . ? C25 C24 C23 120.0(5) . . ? C25 C24 H24 120.0 . . ? C23 C24 H24 120.0 . . ? C24 C25 C21 119.5(5) . . ? C24 C25 H25 120.3 . . ? C21 C25 H25 120.3 . . ? C14 C14 C15 125.7(5) 3_666 . ? C14 C14 H14 117.1 3_666 . ? C15 C14 H14 117.1 . . ? N4 C15 C19 121.5(4) . . ? N4 C15 C14 119.5(3) . . ? C19 C15 C14 118.9(4) . . ? N4 C16 C17 123.6(4) . . ? N4 C16 H16 118.2 . . ? C17 C16 H16 118.2 . . ? C18 C17 C16 118.2(4) . . ? C18 C17 H17 120.9 . . ? C16 C17 H17 120.9 . . ? C17 C18 C19 119.6(4) . . ? C17 C18 H18 120.2 . . ? C19 C18 H18 120.2 . . ? C18 C19 C15 118.9(4) . . ? C18 C19 H19 120.6 . . ? C15 C19 H19 120.6 . . ? C16 N4 C15 118.1(3) . . ? _diffrn_measured_fraction_theta_max 0.803 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 1.291 _refine_diff_density_min -0.590 _refine_diff_density_rms 0.064 #_vrf_PLAT201_shelxlps #; #PROBLEM: Isotropic non-H Atoms in Main Residue(s) 14 #RESPONSE: these atoms correspond to one disordered molecule #and its anisotropic refinement is unstable #; # end Validation Reply Form #===END # end Validation Reply Form #===END data_shelxle_compound_4 _database_code_depnum_ccdc_archive 'CCDC 606787' #======================================================== _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H20 N4' _chemical_formula_sum 'C24 H20 N4' _chemical_formula_weight 364.44 _chemical_compound_source Synthesis 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M 'P -4 21 c' _symmetry_space_group_name_Hall 'P -4 2n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'y, -x, -z' '-x, -y, z' '-y, x, -z' '-x+1/2, y+1/2, -z+1/2' '-y+1/2, -x+1/2, z+1/2' 'x+1/2, -y+1/2, -z+1/2' 'y+1/2, x+1/2, z+1/2' _cell_length_a 15.6498(9) _cell_length_b 15.6498(9) _cell_length_c 16.1138(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3946.5(4) _cell_formula_units_Z 8 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 1500 _cell_measurement_theta_min 1.8139 _cell_measurement_theta_max 28.0854 _exptl_crystal_description Prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.227 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1536 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.930 _exptl_absorpt_correction_T_max 0.990 _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku AFC7S Mercury' _diffrn_measurement_method \w _diffrn_radiation_detector CCD _diffrn_measurement_device ; Mercury (2x2 bin mode) ; _diffrn_detector_area_resol_mean 14.6306 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 44774 _diffrn_reflns_av_R_equivalents 0.0492 _diffrn_reflns_av_sigmaI/netI 0.0225 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 28.10 _reflns_number_total 2310 _reflns_number_gt 1735 _reflns_threshold_expression >2sigma(I) #============================================================================== _computing_data_collection 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_cell_refinement 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_data_reduction 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_structure_solution 'SHELXS-97 (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^)+(0.0601P)^2^+0.8862P] 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_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 2310 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0872 _refine_ls_R_factor_gt 0.0594 _refine_ls_wR_factor_ref 0.1450 _refine_ls_wR_factor_gt 0.1301 _refine_ls_goodness_of_fit_ref 1.110 _refine_ls_restrained_S_all 1.110 _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 C1 C 0.95303(19) 0.9835(2) 0.72642(18) 0.0481(7) Uani 1 1 d . . . H1A H 0.9531 0.9214 0.7180 0.058 Uiso 1 1 calc R . . N1 N 0.8694(2) 1.1037(2) 0.6807(2) 0.0777(9) Uani 1 1 d . . . N2 N 0.9118(2) 0.86092(19) 0.86520(18) 0.0668(8) Uani 1 1 d . . . C2 C 0.94993(19) 1.0026(2) 0.82056(17) 0.0473(7) Uani 1 1 d . . . H2A H 0.9319 1.0618 0.8295 0.057 Uiso 1 1 calc R . . N3 N 0.6044(2) 1.1189(2) 0.41304(18) 0.0684(8) Uani 1 1 d . . . C3 C 0.8924(2) 1.0232(2) 0.6671(2) 0.0527(8) Uani 1 1 d . . . N4 N 0.6119(3) 0.8765(2) 0.6121(2) 0.0947(12) Uani 1 1 d . . . C4 C 0.8186(3) 1.1399(3) 0.6235(3) 0.0946(15) Uani 1 1 d . . . H4A H 0.8025 1.1964 0.6322 0.114 Uiso 1 1 calc R . . C5 C 0.7890(3) 1.1010(3) 0.5546(3) 0.0921(14) Uani 1 1 d . . . H5A H 0.7542 1.1297 0.5171 0.111 Uiso 1 1 calc R . . C6 C 0.8118(3) 1.0189(4) 0.5420(3) 0.0947(15) Uani 1 1 d . . . H6A H 0.7923 0.9893 0.4957 0.114 Uiso 1 1 calc R . . C7 C 0.8642(2) 0.9796(3) 0.5986(2) 0.0754(12) Uani 1 1 d . . . H7A H 0.8806 0.9231 0.5904 0.090 Uiso 1 1 calc R . . C8 C 0.8991(2) 0.9443(2) 0.87516(19) 0.0497(7) Uani 1 1 d . . . C9 C 0.8401(2) 0.9760(3) 0.9306(2) 0.0677(10) Uani 1 1 d . . . H9A H 0.8335 1.0346 0.9371 0.081 Uiso 1 1 calc R . . C10 C 0.7907(3) 0.9203(3) 0.9765(3) 0.0848(13) Uani 1 1 d . . . H10A H 0.7499 0.9408 1.0135 0.102 Uiso 1 1 calc R . . C11 C 0.8026(3) 0.8356(3) 0.9668(2) 0.0841(14) Uani 1 1 d . . . H11A H 0.7701 0.7966 0.9969 0.101 Uiso 1 1 calc R . . C12 C 0.8637(3) 0.8080(3) 0.9116(2) 0.0818(13) Uani 1 1 d . . . H12A H 0.8721 0.7494 0.9059 0.098 Uiso 1 1 calc R . . C13 C 0.54789(19) 0.9879(2) 0.47186(17) 0.0483(7) Uani 1 1 d . . . H13A H 0.5538 0.9260 0.4640 0.058 Uiso 1 1 calc R . . C14 C 0.54896(19) 1.0088(2) 0.56587(18) 0.0506(8) Uani 1 1 d . . . H14A H 0.5592 1.0701 0.5737 0.061 Uiso 1 1 calc R . . C15 C 0.60743(19) 1.0336(2) 0.41423(18) 0.0522(8) Uani 1 1 d . . . C16 C 0.6573(3) 1.1593(3) 0.3606(3) 0.0890(13) Uani 1 1 d . . . H16A H 0.6555 1.2186 0.3589 0.107 Uiso 1 1 calc R . . C17 C 0.7135(3) 1.1182(4) 0.3098(3) 0.0993(17) Uani 1 1 d . . . H17A H 0.7491 1.1492 0.2747 0.119 Uiso 1 1 calc R . . C18 C 0.7170(3) 1.0324(4) 0.3110(3) 0.0956(16) Uani 1 1 d . . . H18A H 0.7549 1.0030 0.2769 0.115 Uiso 1 1 calc R . . C19 C 0.6629(2) 0.9887(3) 0.3642(2) 0.0736(11) Uani 1 1 d . . . H19A H 0.6640 0.9293 0.3661 0.088 Uiso 1 1 calc R . . C20 C 0.6026(2) 0.9590(2) 0.62560(19) 0.0542(8) Uani 1 1 d . . . C21 C 0.6381(3) 0.9982(3) 0.6942(2) 0.0780(11) Uani 1 1 d . . . H21A H 0.6303 1.0565 0.7021 0.094 Uiso 1 1 calc R . . C22 C 0.6840(3) 0.9528(4) 0.7499(3) 0.0992(16) Uani 1 1 d . . . H22A H 0.7059 0.9787 0.7973 0.119 Uiso 1 1 calc R . . C23 C 0.6970(3) 0.8700(4) 0.7351(3) 0.1047(19) Uani 1 1 d . . . H23A H 0.7315 0.8379 0.7702 0.126 Uiso 1 1 calc R . . C24 C 0.6586(4) 0.8327(4) 0.6672(3) 0.122(2) Uani 1 1 d . . . H24A H 0.6655 0.7742 0.6592 0.147 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 C1 0.0460(17) 0.0483(19) 0.0499(16) -0.0004(13) -0.0006(14) 0.0004(15) N1 0.079(2) 0.063(2) 0.091(2) -0.0032(18) -0.0297(19) 0.0102(17) N2 0.089(2) 0.0562(19) 0.0549(17) 0.0005(14) -0.0004(16) -0.0146(16) C2 0.0493(16) 0.0434(15) 0.0493(16) -0.0022(14) 0.0001(14) 0.0019(14) N3 0.073(2) 0.071(2) 0.0612(17) 0.0017(15) 0.0060(15) -0.0206(17) C3 0.0458(17) 0.060(2) 0.0520(18) 0.0044(14) -0.0013(15) -0.0038(16) N4 0.134(3) 0.080(2) 0.070(2) -0.0141(18) -0.035(2) 0.048(2) C4 0.088(3) 0.075(3) 0.120(4) 0.010(3) -0.036(3) 0.018(2) C5 0.077(3) 0.107(4) 0.092(3) 0.027(3) -0.034(2) -0.004(3) C6 0.092(3) 0.128(5) 0.064(2) -0.003(3) -0.029(2) 0.003(3) C7 0.075(3) 0.091(3) 0.060(2) -0.009(2) -0.013(2) 0.010(2) C8 0.0444(17) 0.058(2) 0.0469(16) 0.0002(14) -0.0036(14) -0.0049(15) C9 0.060(2) 0.074(3) 0.069(2) 0.0016(18) 0.0110(19) -0.0003(19) C10 0.064(3) 0.118(4) 0.073(3) 0.001(3) 0.016(2) -0.016(3) C11 0.094(3) 0.103(4) 0.056(2) 0.009(2) -0.001(2) -0.046(3) C12 0.118(4) 0.065(3) 0.063(2) 0.003(2) -0.012(2) -0.031(2) C13 0.0471(17) 0.0493(18) 0.0485(16) -0.0018(14) -0.0015(14) -0.0031(14) C14 0.0516(17) 0.0501(17) 0.0501(16) -0.0024(15) 0.0005(15) -0.0015(15) C15 0.0441(17) 0.068(2) 0.0441(16) -0.0047(14) -0.0025(14) -0.0094(16) C16 0.094(3) 0.098(3) 0.075(3) 0.007(3) 0.006(3) -0.041(3) C17 0.087(3) 0.148(5) 0.063(3) 0.006(3) 0.011(2) -0.052(4) C18 0.061(3) 0.153(5) 0.072(3) -0.026(3) 0.019(2) -0.021(3) C19 0.058(2) 0.094(3) 0.069(2) -0.013(2) 0.0106(19) -0.010(2) C20 0.0472(17) 0.069(2) 0.0460(17) -0.0058(15) 0.0003(14) 0.0079(16) C21 0.081(3) 0.094(3) 0.058(2) -0.009(2) -0.016(2) -0.005(2) C22 0.086(3) 0.146(5) 0.065(3) -0.003(3) -0.018(2) 0.015(3) C23 0.088(3) 0.174(6) 0.052(2) 0.013(3) -0.006(2) 0.063(4) C24 0.159(5) 0.124(4) 0.084(3) -0.003(3) -0.020(4) 0.088(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 C1 C3 1.484(4) . ? C1 C2 1.547(4) . ? C1 C1 1.558(6) 3_775 ? C1 H1A 0.9800 . ? N1 C3 1.328(4) . ? N1 C4 1.342(5) . ? N2 C8 1.330(4) . ? N2 C12 1.347(5) . ? C2 C8 1.496(4) . ? C2 C2 1.569(6) 3_775 ? C2 H2A 0.9800 . ? N3 C15 1.336(4) . ? N3 C16 1.340(5) . ? C3 C7 1.371(5) . ? N4 C20 1.317(5) . ? N4 C24 1.339(5) . ? C4 C5 1.348(6) . ? C4 H4A 0.9300 . ? C5 C6 1.349(7) . ? C5 H5A 0.9300 . ? C6 C7 1.371(6) . ? C6 H6A 0.9300 . ? C7 H7A 0.9300 . ? C8 C9 1.377(5) . ? C9 C10 1.380(5) . ? C9 H9A 0.9300 . ? C10 C11 1.347(6) . ? C10 H10A 0.9300 . ? C11 C12 1.377(6) . ? C11 H11A 0.9300 . ? C12 H12A 0.9300 . ? C13 C15 1.498(4) . ? C13 C13 1.546(6) 3_675 ? C13 C14 1.550(4) . ? C13 H13A 0.9800 . ? C14 C20 1.497(4) . ? C14 C14 1.557(6) 3_675 ? C14 H14A 0.9800 . ? C15 C19 1.377(5) . ? C16 C17 1.364(7) . ? C16 H16A 0.9300 . ? C17 C18 1.344(7) . ? C17 H17A 0.9300 . ? C18 C19 1.385(6) . ? C18 H18A 0.9300 . ? C19 H19A 0.9300 . ? C20 C21 1.380(5) . ? C21 C22 1.351(6) . ? C21 H21A 0.9300 . ? C22 C23 1.333(7) . ? C22 H22A 0.9300 . ? C23 C24 1.378(7) . ? C23 H23A 0.9300 . ? C24 H24A 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 C1 C2 122.1(3) . . ? C3 C1 C1 117.6(3) . 3_775 ? C2 C1 C1 88.02(17) . 3_775 ? C3 C1 H1A 109.1 . . ? C2 C1 H1A 109.1 . . ? C1 C1 H1A 109.1 3_775 . ? C3 N1 C4 116.6(4) . . ? C8 N2 C12 117.0(4) . . ? C8 C2 C1 118.4(3) . . ? C8 C2 C2 120.0(3) . 3_775 ? C1 C2 C2 87.63(17) . 3_775 ? C8 C2 H2A 109.7 . . ? C1 C2 H2A 109.7 . . ? C2 C2 H2A 109.7 3_775 . ? C15 N3 C16 117.3(4) . . ? N1 C3 C7 121.2(3) . . ? N1 C3 C1 117.7(3) . . ? C7 C3 C1 121.1(3) . . ? C20 N4 C24 116.9(4) . . ? N1 C4 C5 125.4(4) . . ? N1 C4 H4A 117.3 . . ? C5 C4 H4A 117.3 . . ? C4 C5 C6 117.5(4) . . ? C4 C5 H5A 121.2 . . ? C6 C5 H5A 121.2 . . ? C5 C6 C7 119.1(4) . . ? C5 C6 H6A 120.5 . . ? C7 C6 H6A 120.5 . . ? C6 C7 C3 120.3(4) . . ? C6 C7 H7A 119.9 . . ? C3 C7 H7A 119.9 . . ? N2 C8 C9 122.1(3) . . ? N2 C8 C2 116.6(3) . . ? C9 C8 C2 121.3(3) . . ? C8 C9 C10 119.8(4) . . ? C8 C9 H9A 120.1 . . ? C10 C9 H9A 120.1 . . ? C11 C10 C9 118.8(4) . . ? C11 C10 H10A 120.6 . . ? C9 C10 H10A 120.6 . . ? C10 C11 C12 118.7(4) . . ? C10 C11 H11A 120.6 . . ? C12 C11 H11A 120.6 . . ? N2 C12 C11 123.6(4) . . ? N2 C12 H12A 118.2 . . ? C11 C12 H12A 118.2 . . ? C15 C13 C13 119.1(3) . 3_675 ? C15 C13 C14 119.9(3) . . ? C13 C13 C14 87.62(18) 3_675 . ? C15 C13 H13A 109.5 . . ? C13 C13 H13A 109.5 3_675 . ? C14 C13 H13A 109.5 . . ? C20 C14 C13 121.6(3) . . ? C20 C14 C14 117.4(3) . 3_675 ? C13 C14 C14 87.25(18) . 3_675 ? C20 C14 H14A 109.6 . . ? C13 C14 H14A 109.6 . . ? C14 C14 H14A 109.6 3_675 . ? N3 C15 C19 121.6(3) . . ? N3 C15 C13 117.7(3) . . ? C19 C15 C13 120.8(3) . . ? N3 C16 C17 123.7(5) . . ? N3 C16 H16A 118.1 . . ? C17 C16 H16A 118.1 . . ? C18 C17 C16 119.2(4) . . ? C18 C17 H17A 120.4 . . ? C16 C17 H17A 120.4 . . ? C17 C18 C19 118.5(4) . . ? C17 C18 H18A 120.7 . . ? C19 C18 H18A 120.7 . . ? C15 C19 C18 119.7(4) . . ? C15 C19 H19A 120.1 . . ? C18 C19 H19A 120.1 . . ? N4 C20 C21 121.6(3) . . ? N4 C20 C14 117.8(3) . . ? C21 C20 C14 120.6(3) . . ? C22 C21 C20 120.8(5) . . ? C22 C21 H21A 119.6 . . ? C20 C21 H21A 119.6 . . ? C23 C22 C21 118.2(5) . . ? C23 C22 H22A 120.9 . . ? C21 C22 H22A 120.9 . . ? C22 C23 C24 119.2(5) . . ? C22 C23 H23A 120.4 . . ? C24 C23 H23A 120.4 . . ? N4 C24 C23 123.2(5) . . ? N4 C24 H24A 118.4 . . ? C23 C24 H24A 118.4 . . ? _diffrn_measured_fraction_theta_max 0.866 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.129 _refine_diff_density_min -0.161 _refine_diff_density_rms 0.035 #===END