Supplementary Material (ESI) for CrystEngComm This journal is (c) The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Neil Champness' 'Sarah A. Barnett' 'Alexander J. Blake' _publ_contact_author_name 'Dr Neil Champness' _publ_contact_author_address ; School of Chemistry University of Nottingham University Park Nottingham NG7 2RD UNITED KINGDOM ; _publ_contact_author_email NEIL.CHAMPNESS@NOTTINGHAM.AC.UK _publ_requested_journal 'Cryst Eng. Comm.' _publ_section_title ; Polymorphism in hydrogen-bonded frameworks; Cyanuric Acid - bis(4-pyridyl)ethene adducts. ; data_Compound(1)-SABBEC _database_code_CSD 206846 _audit_creation_method SHELXL-97 _chemical_name_systematic ; (trans-1,2-Bis(4-pyridyl)ethylene)(cyanuric acid) ; _chemical_name_common '[(4,4-bpe)(cyanuric acid)]' _chemical_formula_moiety 'C3 H3 N3 O3, C12 H10 N2' _chemical_formula_sum 'C15 H13 N5 O3' _chemical_formula_weight 311.30 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 C2/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 26.361(13) _cell_length_b 6.777(3) _cell_length_c 15.553(8) _cell_angle_alpha 90.00 _cell_angle_beta 95.440(8) _cell_angle_gamma 90.00 _cell_volume 2766(4) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1411 _cell_measurement_theta_min 2.63 _cell_measurement_theta_max 28.18 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.495 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1296 _exptl_absorpt_coefficient_mu 0.109 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART1000 CCD area detector' _diffrn_measurement_method omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 8680 _diffrn_reflns_av_R_equivalents 0.105 _diffrn_reflns_av_sigmaI/netI 0.122 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.63 _diffrn_reflns_theta_max 28.57 _reflns_number_total 3445 _reflns_number_gt 1528 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART version 5.624 (Bruker, 2001)' _computing_cell_refinement 'Bruker SAINT version 6.02a (Bruker, 2000)' _computing_data_reduction 'Bruker SAINT; Bruker SHELXTL (Bruker, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'SHELXL-97; PLATON (Spek, 2002)' _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 w=1/[\s^2^(Fo^2^)+(0.0793P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary 'direct methods' _atom_sites_solution_secondary 'difference Fourier synthesis' _atom_sites_solution_hydrogens 'geometrically placed' _refine_ls_hydrogen_treatment 'riding model' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3185 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1436 _refine_ls_R_factor_gt 0.0662 _refine_ls_wR_factor_ref 0.1760 _refine_ls_wR_factor_gt 0.1474 _refine_ls_goodness_of_fit_ref 0.898 _refine_ls_restrained_S_all 0.898 _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 C1 C 0.05501(12) 0.0980(4) 0.3162(2) 0.0297(8) Uani 1 1 d . . . O1 O 0.02563(9) 0.0051(3) 0.35371(18) 0.0445(7) Uani 1 1 d . . . N2 N 0.05570(9) 0.3003(3) 0.31747(17) 0.0267(6) Uani 1 1 d . . . H2A H 0.0314 0.3609 0.3421 0.032 Uiso 1 1 calc R . . C3 C 0.09119(12) 0.4138(4) 0.2835(2) 0.0238(7) Uani 1 1 d . . . O3 O 0.09286(9) 0.5918(3) 0.29264(15) 0.0325(6) Uani 1 1 d . . . N4 N 0.12492(10) 0.3161(3) 0.23855(17) 0.0265(6) Uani 1 1 d . . . H4A H 0.1480 0.3864 0.2150 0.032 Uiso 1 1 calc R . . C5 C 0.12567(12) 0.1149(4) 0.2271(2) 0.0262(7) Uani 1 1 d . . . O5 O 0.15476(9) 0.0368(3) 0.18277(16) 0.0365(6) Uani 1 1 d . . . N6 N 0.09096(10) 0.0145(3) 0.26993(18) 0.0300(7) Uani 1 1 d . . . H6A H 0.0918 -0.1151 0.2675 0.036 Uiso 1 1 calc R . . N7 N 0.47587(10) 1.0635(3) -0.09847(18) 0.0276(6) Uani 1 1 d . . . C8 C 0.45897(12) 0.8783(4) -0.1057(2) 0.0292(8) Uani 1 1 d . . . H8A H 0.4760 0.7892 -0.1403 0.035 Uiso 1 1 calc R . . C9 C 0.41846(12) 0.8101(4) -0.0659(2) 0.0306(8) Uani 1 1 d . . . H9A H 0.4078 0.6768 -0.0737 0.037 Uiso 1 1 calc R . . C10 C 0.39296(12) 0.9343(4) -0.0144(2) 0.0252(7) Uani 1 1 d . . . C11 C 0.41099(12) 1.1278(4) -0.0067(2) 0.0284(8) Uani 1 1 d . . . H11A H 0.3951 1.2198 0.0282 0.034 Uiso 1 1 calc R . . C12 C 0.45111(12) 1.1839(4) -0.0491(2) 0.0295(8) Uani 1 1 d . . . H12A H 0.4623 1.3169 -0.0433 0.035 Uiso 1 1 calc R . . C13 C 0.35062(12) 0.8726(4) 0.0320(2) 0.0282(8) Uani 1 1 d . . . H13A H 0.3349 0.9708 0.0640 0.034 Uiso 1 1 calc R . . C14 C 0.33192(12) 0.6919(4) 0.0340(2) 0.0323(8) Uani 1 1 d . . . H14A H 0.3473 0.5948 0.0008 0.039 Uiso 1 1 calc R . . C15 C 0.29017(12) 0.6272(4) 0.0818(2) 0.0277(8) Uani 1 1 d . . . C16 C 0.27503(13) 0.4292(4) 0.0785(2) 0.0339(8) Uani 1 1 d . . . H16A H 0.2925 0.3372 0.0460 0.041 Uiso 1 1 calc R . . C17 C 0.23556(13) 0.3683(5) 0.1215(2) 0.0341(8) Uani 1 1 d . . . H17A H 0.2262 0.2330 0.1177 0.041 Uiso 1 1 calc R . . N18 N 0.20930(10) 0.4866(3) 0.16840(18) 0.0289(7) Uani 1 1 d . . . C19 C 0.22392(12) 0.6730(4) 0.1736(2) 0.0284(8) Uani 1 1 d . . . H19A H 0.2060 0.7597 0.2080 0.034 Uiso 1 1 calc R . . C20 C 0.26311(12) 0.7490(4) 0.1325(2) 0.0290(8) Uani 1 1 d . . . H20A H 0.2718 0.8847 0.1387 0.035 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 0.0294(19) 0.0170(14) 0.045(2) -0.0044(15) 0.0136(16) -0.0043(12) O1 0.0469(16) 0.0201(11) 0.0719(19) -0.0003(12) 0.0337(14) -0.0072(10) N2 0.0267(15) 0.0157(11) 0.0392(17) -0.0013(12) 0.0112(12) -0.0002(10) C3 0.0247(16) 0.0182(15) 0.0287(19) 0.0026(13) 0.0040(13) 0.0014(12) O3 0.0442(14) 0.0122(10) 0.0426(16) 0.0022(10) 0.0117(11) -0.0013(9) N4 0.0305(15) 0.0138(12) 0.0365(17) 0.0014(12) 0.0103(12) -0.0041(10) C5 0.0275(18) 0.0156(13) 0.037(2) 0.0027(14) 0.0098(15) 0.0003(12) O5 0.0370(14) 0.0202(11) 0.0553(17) -0.0044(11) 0.0202(12) 0.0015(9) N6 0.0326(16) 0.0114(11) 0.048(2) -0.0005(12) 0.0158(14) 0.0002(10) N7 0.0267(15) 0.0225(13) 0.0346(17) 0.0054(12) 0.0085(12) 0.0016(11) C8 0.0316(19) 0.0229(15) 0.033(2) -0.0005(14) 0.0057(15) 0.0002(13) C9 0.0295(18) 0.0233(15) 0.039(2) -0.0037(15) 0.0055(16) -0.0028(13) C10 0.0234(17) 0.0218(15) 0.0305(19) 0.0026(14) 0.0032(14) -0.0007(12) C11 0.0273(18) 0.0236(15) 0.035(2) -0.0005(14) 0.0081(15) 0.0039(12) C12 0.0306(18) 0.0222(15) 0.036(2) 0.0013(15) 0.0069(15) 0.0006(13) C13 0.0244(17) 0.0258(16) 0.035(2) 0.0000(14) 0.0038(15) 0.0028(12) C14 0.0326(19) 0.0281(17) 0.037(2) 0.0005(16) 0.0091(16) -0.0013(14) C15 0.0246(17) 0.0270(16) 0.032(2) 0.0041(14) 0.0034(15) -0.0027(12) C16 0.038(2) 0.0214(15) 0.044(2) -0.0013(15) 0.0147(17) -0.0037(14) C17 0.035(2) 0.0233(16) 0.046(2) -0.0011(15) 0.0132(17) -0.0016(14) N18 0.0300(16) 0.0228(13) 0.0354(17) 0.0046(12) 0.0113(13) 0.0000(11) C19 0.0298(18) 0.0229(16) 0.034(2) 0.0000(14) 0.0104(15) 0.0047(13) C20 0.0310(18) 0.0174(15) 0.039(2) 0.0003(14) 0.0058(16) -0.0054(12) _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 O1 1.193(4) . ? C1 N6 1.366(4) . ? C1 N2 1.371(3) . ? N2 C3 1.357(4) . ? C3 O3 1.215(3) . ? C3 N4 1.354(4) . ? N4 C5 1.375(3) . ? C5 O5 1.202(4) . ? C5 N6 1.364(4) . ? N7 C8 1.333(4) . ? N7 C12 1.334(4) . ? C8 C9 1.365(4) . ? C9 C10 1.379(4) . ? C10 C11 1.396(4) . ? C10 C13 1.448(4) . ? C11 C12 1.353(4) . ? C13 C14 1.321(4) . ? C14 C15 1.454(4) . ? C15 C20 1.385(4) . ? C15 C16 1.399(4) . ? C16 C17 1.353(4) . ? C17 N18 1.323(4) . ? N18 C19 1.321(4) . ? C19 C20 1.366(4) . ? 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 O1 C1 N6 123.6(3) . . ? O1 C1 N2 122.0(3) . . ? N6 C1 N2 114.4(3) . . ? C3 N2 C1 124.8(3) . . ? O3 C3 N4 121.8(3) . . ? O3 C3 N2 122.4(3) . . ? N4 C3 N2 115.8(2) . . ? C3 N4 C5 124.7(3) . . ? O5 C5 N6 123.7(3) . . ? O5 C5 N4 121.9(3) . . ? N6 C5 N4 114.4(3) . . ? C5 N6 C1 125.6(2) . . ? C8 N7 C12 116.6(3) . . ? N7 C8 C9 123.4(3) . . ? C8 C9 C10 120.1(3) . . ? C9 C10 C11 116.3(3) . . ? C9 C10 C13 123.7(3) . . ? C11 C10 C13 120.0(3) . . ? C12 C11 C10 119.8(3) . . ? N7 C12 C11 123.8(3) . . ? C14 C13 C10 125.9(3) . . ? C13 C14 C15 126.4(3) . . ? C20 C15 C16 115.6(3) . . ? C20 C15 C14 124.5(3) . . ? C16 C15 C14 119.8(3) . . ? C17 C16 C15 120.3(3) . . ? N18 C17 C16 123.7(3) . . ? C19 N18 C17 116.6(3) . . ? N18 C19 C20 124.2(3) . . ? C19 C20 C15 119.6(3) . . ? _diffrn_measured_fraction_theta_max 0.902 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 0.23 _refine_diff_density_min -0.29 _refine_diff_density_rms 0.07 #===END data_Compound(2)-CYABPE _database_code_CSD 206847 _exptl_special_details ; The double bond of the bis(4-pyridyl)ethylene ligand shows some sign of disorder. This is where the highest residual electron density is located. However, this has not been modelled because the electron density peaks are relatively small (less than 1 e.A^-3) in this region and in order to get a sensible model the rest of the molecule would have to be modelled. It was found that the double bond distances were significantly different for the two bis(4-pyridyl)ethylene ligands found. A SADI restraint has been applied and the distances now agree to within 3 sigma. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; (trans-1,2-Bis(4-pyridyl)ethylene)(cyanuric acid) ; _chemical_name_common '[(4,4-bpe)(cyanuric acid)]' _chemical_formula_moiety 'C12 H10 N2, C3 H3 N3 O3' _chemical_formula_sum 'C15 H13 N5 O3' _chemical_formula_weight 311.30 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 C2/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 19.174(3) _cell_length_b 6.7825(10) _cell_length_c 32.748(5) _cell_angle_alpha 90.00 _cell_angle_beta 91.246(3) _cell_angle_gamma 90.00 _cell_volume 4259(2) _cell_formula_units_Z 12 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2783 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 27.10 _exptl_crystal_description 'Column cut from crystal block' _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.457 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1944 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART1000 CCD area detector' _diffrn_measurement_method omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 13409 _diffrn_reflns_av_R_equivalents 0.056 _diffrn_reflns_av_sigmaI/netI 0.045 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -40 _diffrn_reflns_limit_l_max 44 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 26.00 _reflns_number_total 5254 _reflns_number_gt 2754 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART version 5.624 (Bruker, 2001)' _computing_cell_refinement 'Bruker SAINT version 6.02a (Bruker, 2000)' _computing_data_reduction 'Bruker SAINT; Bruker SHELXTL (Bruker, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'SHELXL-97; PLATON (Spek, 2002)' _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 w=1/[\s^2^(Fo^2^)+(0.086P)^2^+0.691P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary 'direct methods' _atom_sites_solution_secondary 'difference Fourier synthesis' _atom_sites_solution_hydrogens 'geometrically placed' _refine_ls_hydrogen_treatment 'riding model' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4157 _refine_ls_number_parameters 313 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0901 _refine_ls_R_factor_gt 0.0568 _refine_ls_wR_factor_ref 0.1563 _refine_ls_wR_factor_gt 0.1425 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.031 _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 C1 C 0.16563(12) 0.7742(3) -0.13338(7) 0.0191(5) Uani 1 1 d . . . O1 O 0.17774(9) 0.5964(2) -0.13349(5) 0.0269(4) Uani 1 1 d . . . N2 N 0.15612(10) 0.8753(3) -0.09771(6) 0.0195(5) Uani 1 1 d . . . H2A H 0.1567 0.8073 -0.0748 0.023 Uiso 1 1 calc R . . C3 C 0.14576(12) 1.0746(3) -0.09509(8) 0.0214(5) Uani 1 1 d . . . O3 O 0.13769(10) 1.1586(2) -0.06262(5) 0.0314(5) Uani 1 1 d . . . N4 N 0.14436(10) 1.1727(3) -0.13168(6) 0.0221(5) Uani 1 1 d . . . H4A H 0.1392 1.3016 -0.1311 0.027 Uiso 1 1 calc R . . C5 C 0.15037(12) 1.0847(3) -0.16942(8) 0.0218(6) Uani 1 1 d . . . O5 O 0.14695(9) 1.1767(2) -0.20113(5) 0.0287(4) Uani 1 1 d . . . N6 N 0.16136(10) 0.8838(3) -0.16804(6) 0.0209(5) Uani 1 1 d . . . H6A H 0.1660 0.8218 -0.1914 0.025 Uiso 1 1 calc R . . N7 N 0.17204(11) 0.2493(3) 0.25234(6) 0.0256(5) Uani 1 1 d . . . C8 C 0.18708(13) 0.1156(4) 0.22367(8) 0.0292(6) Uani 1 1 d . . . H8A H 0.1960 -0.0160 0.2323 0.035 Uiso 1 1 calc R . . C9 C 0.19033(14) 0.1561(4) 0.18313(8) 0.0335(7) Uani 1 1 d . . . H9A H 0.2026 0.0554 0.1644 0.040 Uiso 1 1 calc R . . C10 C 0.17583(13) 0.3428(4) 0.16923(8) 0.0326(7) Uani 1 1 d . . . C11 C 0.15912(13) 0.4836(4) 0.19802(9) 0.0340(7) Uani 1 1 d . . . H11A H 0.1484 0.6146 0.1897 0.041 Uiso 1 1 calc R . . C12 C 0.15809(13) 0.4327(4) 0.23910(8) 0.0293(6) Uani 1 1 d . . . H12A H 0.1471 0.5313 0.2585 0.035 Uiso 1 1 calc R . . C13 C 0.17983(14) 0.3823(4) 0.12488(9) 0.0384(7) Uani 1 1 d D . . H13A H 0.1922 0.2763 0.1075 0.046 Uiso 1 1 calc R . . C14 C 0.16749(14) 0.5531(4) 0.10824(9) 0.0400(7) Uani 1 1 d D . . H14A H 0.1560 0.6585 0.1260 0.048 Uiso 1 1 calc R . . C15 C 0.16978(13) 0.5979(4) 0.06358(8) 0.0313(6) Uani 1 1 d . . . C16 C 0.18361(13) 0.4626(4) 0.03286(9) 0.0327(7) Uani 1 1 d . . . H16A H 0.1947 0.3298 0.0395 0.039 Uiso 1 1 calc R . . C17 C 0.18109(13) 0.5235(4) -0.00741(8) 0.0268(6) Uani 1 1 d . . . H17A H 0.1905 0.4290 -0.0280 0.032 Uiso 1 1 calc R . . N18 N 0.16605(10) 0.7085(3) -0.01910(6) 0.0218(5) Uani 1 1 d . . . C19 C 0.15364(13) 0.8358(4) 0.01106(8) 0.0275(6) Uani 1 1 d . . . H19A H 0.1433 0.9685 0.0038 0.033 Uiso 1 1 calc R . . C20 C 0.15483(13) 0.7875(4) 0.05166(8) 0.0312(6) Uani 1 1 d . . . H20A H 0.1453 0.8851 0.0716 0.037 Uiso 1 1 calc R . . C21 C 0.01044(12) -0.1081(3) 0.21350(7) 0.0214(5) Uani 1 1 d . . . O21 O 0.02138(10) -0.1962(2) 0.18190(5) 0.0311(5) Uani 1 1 d . . . N22 N 0.00747(10) 0.0936(3) 0.21512(6) 0.0205(5) Uani 1 1 d . . . H22A H 0.0106 0.1584 0.1920 0.025 Uiso 1 1 calc R . . C23 C 0.0000 0.2016(5) 0.2500 0.0199(7) Uani 1 2 d S . . O23 O 0.0000 0.3824(3) 0.2500 0.0276(6) Uani 1 2 d S . . N26 N 0.0000 -0.2022(4) 0.2500 0.0236(7) Uani 1 2 d S . . H26A H 0.0000 -0.3319 0.2500 0.028 Uiso 1 2 calc SR . . N27 N 0.00753(10) 0.2462(3) 0.13416(6) 0.0220(5) Uani 1 1 d . . . C28 C 0.02107(13) 0.1190(3) 0.10423(8) 0.0246(6) Uani 1 1 d . . . H28A H 0.0311 -0.0139 0.1115 0.030 Uiso 1 1 calc R . . C29 C 0.02134(13) 0.1692(3) 0.06363(7) 0.0240(6) Uani 1 1 d . . . H29A H 0.0319 0.0721 0.0438 0.029 Uiso 1 1 calc R . . C30 C 0.00623(12) 0.3611(3) 0.05129(8) 0.0230(6) Uani 1 1 d . . . C31 C -0.00905(13) 0.4936(3) 0.08230(8) 0.0247(6) Uani 1 1 d . . . H31A H -0.0207 0.6262 0.0758 0.030 Uiso 1 1 calc R . . C32 C -0.00720(12) 0.4321(4) 0.12263(8) 0.0241(6) Uani 1 1 d . . . H32A H -0.0168 0.5262 0.1432 0.029 Uiso 1 1 calc R . . C33 C 0.00840(12) 0.4141(3) 0.00802(7) 0.0245(6) Uani 1 1 d D . . H33A H 0.0234 0.3148 -0.0103 0.029 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 0.0182(12) 0.0172(12) 0.0220(14) -0.0010(10) 0.0005(10) -0.0008(9) O1 0.0375(11) 0.0146(9) 0.0287(11) -0.0009(7) 0.0041(8) 0.0018(7) N2 0.0258(11) 0.0146(9) 0.0180(11) 0.0029(8) 0.0006(9) 0.0005(8) C3 0.0231(13) 0.0167(11) 0.0242(14) -0.0011(10) -0.0021(10) -0.0001(10) O3 0.0516(12) 0.0222(9) 0.0205(10) -0.0052(8) -0.0003(9) 0.0040(8) N4 0.0294(12) 0.0132(9) 0.0237(12) 0.0002(8) -0.0031(9) 0.0021(8) C5 0.0202(13) 0.0208(12) 0.0243(15) -0.0015(11) -0.0026(10) -0.0016(10) O5 0.0387(11) 0.0238(9) 0.0235(10) 0.0059(8) -0.0042(8) 0.0004(8) N6 0.0295(12) 0.0174(10) 0.0159(11) -0.0017(8) 0.0006(9) 0.0011(8) N7 0.0273(12) 0.0283(11) 0.0210(12) 0.0050(9) -0.0012(9) -0.0004(9) C8 0.0284(15) 0.0323(14) 0.0270(16) -0.0014(12) -0.0010(12) 0.0013(11) C9 0.0310(16) 0.0455(17) 0.0240(15) -0.0065(13) 0.0024(12) -0.0010(12) C10 0.0212(14) 0.0555(18) 0.0208(15) 0.0023(14) -0.0027(11) -0.0073(12) C11 0.0304(15) 0.0337(15) 0.0375(17) 0.0187(13) -0.0053(13) -0.0009(12) C12 0.0313(15) 0.0266(13) 0.0300(16) -0.0008(12) 0.0025(12) -0.0012(11) C13 0.0279(16) 0.0404(17) 0.0468(19) -0.0026(14) -0.0024(13) -0.0027(12) C14 0.0319(16) 0.0373(16) 0.051(2) -0.0014(14) -0.0043(14) -0.0033(13) C15 0.0183(13) 0.0544(18) 0.0213(15) 0.0027(13) -0.0018(11) -0.0071(12) C16 0.0231(14) 0.0298(14) 0.0448(18) 0.0203(13) -0.0061(13) -0.0053(11) C17 0.0249(14) 0.0248(13) 0.0306(15) -0.0011(11) -0.0006(12) -0.0025(11) N18 0.0216(11) 0.0254(10) 0.0183(11) 0.0023(9) -0.0020(9) -0.0015(9) C19 0.0280(15) 0.0299(13) 0.0246(15) -0.0009(11) 0.0027(11) 0.0012(11) C20 0.0321(16) 0.0394(16) 0.0222(15) -0.0026(12) 0.0007(12) -0.0009(12) C21 0.0249(13) 0.0165(12) 0.0225(14) -0.0022(10) -0.0038(10) -0.0003(10) O21 0.0512(12) 0.0210(9) 0.0210(10) -0.0048(8) 0.0001(9) 0.0024(8) N22 0.0300(12) 0.0134(9) 0.0181(11) 0.0025(8) -0.0009(9) 0.0015(8) C23 0.0209(18) 0.0159(16) 0.023(2) 0.000 -0.0012(15) 0.000 O23 0.0396(16) 0.0110(12) 0.0325(15) 0.000 0.0050(12) 0.000 N26 0.0388(18) 0.0097(13) 0.0219(17) 0.000 -0.0040(14) 0.000 N27 0.0224(11) 0.0228(11) 0.0206(12) 0.0020(9) -0.0023(9) -0.0005(8) C28 0.0294(14) 0.0195(12) 0.0249(14) 0.0007(10) 0.0019(11) 0.0000(10) C29 0.0261(14) 0.0270(13) 0.0190(14) -0.0042(11) 0.0003(11) 0.0011(11) C30 0.0169(13) 0.0276(13) 0.0243(14) 0.0008(11) -0.0010(10) -0.0028(10) C31 0.0259(14) 0.0204(12) 0.0279(15) 0.0055(11) -0.0016(11) 0.0004(10) C32 0.0241(14) 0.0238(13) 0.0243(14) -0.0034(11) 0.0000(11) -0.0008(10) C33 0.0266(14) 0.0269(12) 0.0199(14) 0.0001(11) -0.0007(11) -0.0002(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 C1 O1 1.228(3) . ? C1 N6 1.358(3) . ? C1 N2 1.370(3) . ? N2 C3 1.369(3) . ? C3 O3 1.219(3) . ? C3 N4 1.370(3) . ? N4 C5 1.380(3) . ? C5 O5 1.212(3) . ? C5 N6 1.379(3) . ? N7 C8 1.341(3) . ? N7 C12 1.342(3) . ? C8 C9 1.359(4) . ? C9 C10 1.372(4) . ? C10 C11 1.385(4) . ? C10 C13 1.480(4) . ? C11 C12 1.390(4) . ? C13 C14 1.299(3) . ? C14 C15 1.495(4) . ? C15 C20 1.372(4) . ? C15 C16 1.392(4) . ? C16 C17 1.382(4) . ? C17 N18 1.341(3) . ? N18 C19 1.337(3) . ? C19 C20 1.369(4) . ? C21 O21 1.217(3) . ? C21 N22 1.370(3) . ? C21 N26 1.373(3) . ? N22 C23 1.367(2) . ? C23 O23 1.226(4) . ? C23 N22 1.367(2) 2 ? N26 C21 1.373(3) 2 ? N27 C28 1.336(3) . ? N27 C32 1.344(3) . ? C28 C29 1.373(3) . ? C29 C30 1.392(3) . ? C30 C31 1.392(3) . ? C30 C33 1.463(3) . ? C31 C32 1.385(3) . ? C33 C33 1.315(4) 5_565 ? 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 O1 C1 N6 122.9(2) . . ? O1 C1 N2 121.5(2) . . ? N6 C1 N2 115.58(19) . . ? C3 N2 C1 124.8(2) . . ? O3 C3 N2 122.5(2) . . ? O3 C3 N4 122.4(2) . . ? N2 C3 N4 115.1(2) . . ? C3 N4 C5 124.9(2) . . ? O5 C5 N6 122.8(2) . . ? O5 C5 N4 122.7(2) . . ? N6 C5 N4 114.4(2) . . ? C1 N6 C5 125.1(2) . . ? C8 N7 C12 116.4(2) . . ? N7 C8 C9 124.2(2) . . ? C8 C9 C10 119.8(3) . . ? C9 C10 C11 117.3(2) . . ? C9 C10 C13 118.5(3) . . ? C11 C10 C13 124.1(3) . . ? C10 C11 C12 119.8(2) . . ? N7 C12 C11 122.4(2) . . ? C14 C13 C10 124.0(3) . . ? C13 C14 C15 125.6(3) . . ? C20 C15 C16 117.0(2) . . ? C20 C15 C14 117.3(3) . . ? C16 C15 C14 125.7(3) . . ? C17 C16 C15 119.3(2) . . ? N18 C17 C16 123.7(2) . . ? C19 N18 C17 115.7(2) . . ? N18 C19 C20 124.3(2) . . ? C19 C20 C15 120.0(3) . . ? O21 C21 N22 122.1(2) . . ? O21 C21 N26 122.9(2) . . ? N22 C21 N26 115.0(2) . . ? C23 N22 C21 124.9(2) . . ? O23 C23 N22 122.42(14) . 2 ? O23 C23 N22 122.42(14) . . ? N22 C23 N22 115.2(3) 2 . ? C21 N26 C21 124.6(3) 2 . ? C28 N27 C32 116.3(2) . . ? N27 C28 C29 123.7(2) . . ? C28 C29 C30 120.6(2) . . ? C29 C30 C31 116.0(2) . . ? C29 C30 C33 120.1(2) . . ? C31 C30 C33 124.0(2) . . ? C32 C31 C30 120.0(2) . . ? N27 C32 C31 123.5(2) . . ? C33 C33 C30 126.3(3) 5_565 . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.85 _refine_diff_density_min -0.36 _refine_diff_density_rms 0.06 #===END