data_global _journal_coden_Cambridge 91 loop_ _publ_author_name 'Duncan Graham' 'Ljiljana Fruk' 'W. Ewen Smith' _publ_contact_author_name 'Dr Duncan Graham' _publ_contact_author_address ; Pure and Applied Chemistry University of Strathclyde 295 Cathedral Street Glasgow G1 1XL UNITED KINGDOM ; _publ_contact_author_email DUNCAN.GRAHAM@STRATH.AC.UK _publ_requested_journal 'The Analyst' _publ_section_title ; Detection of DNA Probes Using Diels Alder Cycloaddition and SERRS ; data_d5 _database_code_CSD 200427 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H12 N6 O3' _chemical_formula_weight 348.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 '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' 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.3995(3) _cell_length_b 12.2923(3) _cell_length_c 17.5766(5) _cell_angle_alpha 90.00 _cell_angle_beta 92.7660(10) _cell_angle_gamma 90.00 _cell_volume 3107.49(13) _cell_formula_units_Z 8 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 7630 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.88 _exptl_crystal_description 'cut needle' _exptl_crystal_colour orange _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.489 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1440 _exptl_absorpt_coefficient_mu 0.108 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(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 'Nonius Kappa CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 11834 _diffrn_reflns_av_R_equivalents 0.0601 _diffrn_reflns_av_sigmaI/netI 0.0807 _diffrn_reflns_limit_h_min 0 _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 2.02 _diffrn_reflns_theta_max 26.00 _reflns_number_total 6111 _reflns_number_gt 3643 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Denzo & Collect' _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0590P)^2^+0.8715P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6111 _refine_ls_number_parameters 479 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1118 _refine_ls_R_factor_gt 0.0540 _refine_ls_wR_factor_ref 0.1356 _refine_ls_wR_factor_gt 0.1138 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.23041(12) 0.60751(15) -0.30978(10) 0.0334(5) Uani 1 d . . . O2 O -0.09414(12) 0.24482(14) -0.04625(10) 0.0338(5) Uani 1 d . . . O3 O 0.17448(13) 0.08803(16) 0.04543(12) 0.0462(6) Uani 1 d . . . O4 O 0.26041(13) 0.29627(16) 0.27833(11) 0.0449(5) Uani 1 d . . . O5 O 0.28415(13) 0.88951(17) -0.08127(12) 0.0503(6) Uani 1 d . . . O6 O 0.54317(12) 0.77272(15) 0.05503(10) 0.0373(5) Uani 1 d . . . N1 N 0.06160(13) 0.49984(17) 0.24248(11) 0.0244(5) Uani 1 d . . . N2 N 0.08221(13) 0.58318(17) 0.20052(12) 0.0255(5) Uani 1 d . . . N3 N 0.09055(13) 0.54886(18) 0.12772(12) 0.0219(5) Uani 1 d . . . H1 H 0.0993(18) 0.596(2) 0.0905(16) 0.048(9) Uiso 1 d . . . N4 N 0.09684(13) 0.38853(17) -0.01442(11) 0.0225(5) Uani 1 d . . . N5 N 0.12360(12) 0.48638(17) -0.02286(11) 0.0216(5) Uani 1 d . . . N6 N 0.03882(13) 0.18264(16) 0.01898(11) 0.0241(5) Uani 1 d . . . N7 N 0.46327(14) 0.48854(18) -0.24458(12) 0.0288(5) Uani 1 d . . . N8 N 0.44488(14) 0.40262(18) -0.20461(12) 0.0308(5) Uani 1 d . . . N9 N 0.42354(14) 0.43370(18) -0.13398(13) 0.0274(5) Uani 1 d . . . H2 H 0.4120(19) 0.386(3) -0.0972(17) 0.054(10) Uiso 1 d . . . N10 N 0.38388(13) 0.58776(18) 0.00548(11) 0.0255(5) Uani 1 d . . . N11 N 0.36919(13) 0.48578(18) 0.01017(12) 0.0259(5) Uani 1 d . . . N12 N 0.41598(13) 0.80667(16) -0.02761(11) 0.0259(5) Uani 1 d . . . C1 C 0.07221(15) 0.3666(2) 0.06054(13) 0.0201(6) Uani 1 d . . . C2 C 0.04607(15) 0.2610(2) 0.07893(14) 0.0220(6) Uani 1 d . . . C3 C 0.02720(15) 0.2289(2) 0.15321(14) 0.0239(6) Uani 1 d . . . H3 H 0.0106 0.1554 0.1625 0.029 Uiso 1 calc R . . C4 C 0.03218(15) 0.3012(2) 0.21256(14) 0.0236(6) Uani 1 d . . . H4 H 0.0207 0.2790 0.2630 0.028 Uiso 1 calc R . . C5 C 0.05495(15) 0.4093(2) 0.19593(13) 0.0211(6) Uani 1 d . . . C6 C 0.07397(15) 0.4411(2) 0.12194(14) 0.0203(6) Uani 1 d . . . C7 C 0.15189(15) 0.5121(2) -0.09647(14) 0.0226(6) Uani 1 d . . . C8 C 0.15484(16) 0.4383(2) -0.15737(14) 0.0270(6) Uani 1 d . . . H8 H 0.1377 0.3645 -0.1504 0.032 Uiso 1 calc R . . C9 C 0.18251(16) 0.4730(2) -0.22683(15) 0.0286(6) Uani 1 d . . . H9 H 0.1850 0.4228 -0.2678 0.034 Uiso 1 calc R . . C10 C 0.20710(16) 0.5816(2) -0.23793(14) 0.0259(6) Uani 1 d . . . C11 C 0.20668(15) 0.6544(2) -0.17770(14) 0.0247(6) Uani 1 d . . . H11 H 0.2250 0.7279 -0.1845 0.030 Uiso 1 calc R . . C12 C 0.17919(15) 0.6188(2) -0.10762(14) 0.0242(6) Uani 1 d . . . H12 H 0.1790 0.6685 -0.0662 0.029 Uiso 1 calc R . . C13 C 0.25538(18) 0.7178(2) -0.32417(15) 0.0327(7) Uani 1 d . . . H13A H 0.2048 0.7660 -0.3101 0.039 Uiso 1 calc R . . H13B H 0.2663 0.7268 -0.3784 0.039 Uiso 1 calc R . . H13C H 0.3121 0.7362 -0.2939 0.039 Uiso 1 calc R . . C14 C -0.02908(18) 0.1831(2) -0.04074(14) 0.0270(6) Uani 1 d . . . C15 C -0.00423(19) 0.0939(2) -0.09302(15) 0.0313(7) Uani 1 d . . . H15 H -0.0389 0.0728 -0.1380 0.038 Uiso 1 calc R . . C16 C 0.07395(19) 0.0490(2) -0.06667(16) 0.0359(7) Uani 1 d . . . H16 H 0.1051 -0.0094 -0.0900 0.043 Uiso 1 calc R . . C17 C 0.10572(18) 0.1039(2) 0.00505(15) 0.0315(7) Uani 1 d . . . C18 C 0.41346(15) 0.6168(2) -0.06689(14) 0.0217(6) Uani 1 d . . . C19 C 0.42938(16) 0.7254(2) -0.08411(14) 0.0239(6) Uani 1 d . . . C20 C 0.45744(16) 0.7606(2) -0.15555(14) 0.0260(6) Uani 1 d . . . H20 H 0.4676 0.8360 -0.1639 0.031 Uiso 1 calc R . . C21 C 0.47047(16) 0.6883(2) -0.21346(14) 0.0261(6) Uani 1 d . . . H21 H 0.4895 0.7120 -0.2618 0.031 Uiso 1 calc R . . C22 C 0.45463(15) 0.5784(2) -0.19843(14) 0.0235(6) Uani 1 d . . . C23 C 0.42822(15) 0.5436(2) -0.12716(14) 0.0213(6) Uani 1 d . . . C24 C 0.33905(16) 0.4479(2) 0.08082(15) 0.0275(6) Uani 1 d . . . C25 C 0.33251(16) 0.5106(2) 0.14606(15) 0.0341(7) Uani 1 d . . . H25 H 0.3461 0.5862 0.1448 0.041 Uiso 1 calc R . . C26 C 0.30583(16) 0.4622(2) 0.21380(16) 0.0351(7) Uani 1 d . . . H26 H 0.3014 0.5042 0.2588 0.042 Uiso 1 calc R . . C27 C 0.28597(16) 0.3518(2) 0.21394(16) 0.0326(7) Uani 1 d . . . C28 C 0.29056(17) 0.2891(2) 0.14926(16) 0.0362(7) Uani 1 d . . . H28 H 0.2753 0.2139 0.1503 0.043 Uiso 1 calc R . . C29 C 0.31748(16) 0.3370(2) 0.08328(16) 0.0324(7) Uani 1 d . . . H29 H 0.3215 0.2941 0.0386 0.039 Uiso 1 calc R . . C30 C 0.2647(2) 0.3531(3) 0.34693(17) 0.0532(9) Uani 1 d . . . H30A H 0.2452 0.3054 0.3879 0.064 Uiso 0.50 calc PR . . H30B H 0.2233 0.4164 0.3429 0.064 Uiso 0.50 calc PR . . H30C H 0.3286 0.3777 0.3583 0.064 Uiso 0.50 calc PR . . H30D H 0.2862 0.4275 0.3382 0.064 Uiso 0.50 calc PR . . H30E H 0.3081 0.3166 0.3832 0.064 Uiso 0.50 calc PR . . H30F H 0.2028 0.3553 0.3677 0.064 Uiso 0.50 calc PR . . C31 C 0.34470(18) 0.8846(2) -0.03151(16) 0.0334(7) Uani 1 d . . . C32 C 0.36106(19) 0.9557(2) 0.03605(16) 0.0381(7) Uani 1 d . . . H32 H 0.3236 1.0160 0.0489 0.046 Uiso 1 calc R . . C33 C 0.43601(18) 0.9217(2) 0.07548(15) 0.0333(7) Uani 1 d . . . H33 H 0.4611 0.9537 0.1212 0.040 Uiso 1 calc R . . C34 C 0.47462(18) 0.8255(2) 0.03694(14) 0.0288(6) Uani 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 O1 0.0413(11) 0.0354(12) 0.0241(11) 0.0039(9) 0.0068(8) 0.0005(9) O2 0.0416(11) 0.0258(11) 0.0331(12) 0.0008(9) -0.0073(9) 0.0033(9) O3 0.0378(11) 0.0461(14) 0.0543(14) -0.0108(11) -0.0031(10) 0.0148(10) O4 0.0485(12) 0.0464(13) 0.0405(13) 0.0057(11) 0.0090(10) 0.0001(10) O5 0.0458(12) 0.0466(14) 0.0563(15) -0.0155(11) -0.0190(11) 0.0204(10) O6 0.0430(11) 0.0307(12) 0.0370(12) -0.0001(9) -0.0108(9) 0.0058(9) N1 0.0283(11) 0.0226(12) 0.0221(12) -0.0016(10) 0.0005(9) 0.0003(10) N2 0.0301(11) 0.0226(13) 0.0238(13) -0.0037(10) -0.0001(9) 0.0013(10) N3 0.0275(12) 0.0185(13) 0.0196(13) -0.0001(10) -0.0002(9) -0.0003(9) N4 0.0207(10) 0.0226(13) 0.0242(12) 0.0017(10) 0.0000(9) 0.0035(9) N5 0.0209(11) 0.0232(13) 0.0208(12) 0.0031(10) 0.0003(8) 0.0029(9) N6 0.0324(12) 0.0170(12) 0.0230(12) -0.0024(9) 0.0023(9) 0.0023(9) N7 0.0318(12) 0.0280(13) 0.0266(13) -0.0001(11) 0.0013(9) 0.0039(10) N8 0.0384(13) 0.0263(14) 0.0281(14) -0.0049(11) 0.0039(10) 0.0022(11) N9 0.0344(13) 0.0224(14) 0.0253(14) -0.0007(11) 0.0013(10) 0.0025(10) N10 0.0229(11) 0.0278(14) 0.0255(13) 0.0015(10) -0.0012(9) 0.0039(10) N11 0.0219(11) 0.0281(14) 0.0277(13) 0.0073(10) 0.0003(9) 0.0031(10) N12 0.0308(12) 0.0206(12) 0.0261(13) -0.0024(10) -0.0026(9) 0.0042(10) C1 0.0174(12) 0.0228(15) 0.0201(14) 0.0004(11) 0.0000(10) 0.0053(10) C2 0.0229(13) 0.0210(14) 0.0218(15) -0.0020(11) -0.0007(10) 0.0043(11) C3 0.0244(13) 0.0198(14) 0.0276(16) 0.0043(12) 0.0030(11) 0.0005(11) C4 0.0257(13) 0.0258(16) 0.0195(14) 0.0010(12) 0.0012(10) 0.0030(11) C5 0.0197(12) 0.0233(15) 0.0202(14) -0.0013(11) -0.0019(10) 0.0006(11) C6 0.0169(12) 0.0202(15) 0.0237(15) 0.0019(11) -0.0025(10) 0.0027(10) C7 0.0164(12) 0.0268(15) 0.0244(15) -0.0013(12) -0.0003(10) 0.0009(11) C8 0.0290(14) 0.0252(16) 0.0268(16) 0.0009(12) 0.0015(11) -0.0008(12) C9 0.0324(15) 0.0293(17) 0.0244(16) -0.0042(12) 0.0029(11) 0.0008(12) C10 0.0189(13) 0.0336(17) 0.0252(16) 0.0041(13) 0.0019(10) 0.0043(12) C11 0.0212(13) 0.0251(15) 0.0278(15) 0.0025(12) 0.0009(11) 0.0011(11) C12 0.0210(13) 0.0283(16) 0.0230(15) -0.0017(12) -0.0007(10) 0.0006(11) C13 0.0314(15) 0.0390(19) 0.0278(16) 0.0117(13) 0.0017(11) 0.0017(13) C14 0.0369(15) 0.0223(15) 0.0218(15) 0.0030(12) 0.0011(12) -0.0055(13) C15 0.0461(17) 0.0255(16) 0.0228(15) -0.0020(12) 0.0059(12) -0.0073(13) C16 0.0479(18) 0.0260(16) 0.0352(18) -0.0096(13) 0.0160(14) -0.0040(14) C17 0.0350(16) 0.0251(16) 0.0350(17) -0.0009(13) 0.0084(13) 0.0028(13) C18 0.0190(12) 0.0235(15) 0.0223(15) 0.0014(11) -0.0018(10) 0.0042(11) C19 0.0234(13) 0.0232(15) 0.0248(15) -0.0017(12) -0.0029(11) 0.0041(11) C20 0.0266(13) 0.0204(15) 0.0304(16) 0.0043(12) -0.0034(11) 0.0005(11) C21 0.0235(13) 0.0308(17) 0.0238(15) 0.0032(12) -0.0015(11) 0.0016(12) C22 0.0208(13) 0.0264(16) 0.0230(15) 0.0003(12) -0.0006(10) 0.0039(11) C23 0.0168(12) 0.0207(15) 0.0262(15) 0.0006(11) -0.0022(10) 0.0009(11) C24 0.0174(12) 0.0392(18) 0.0258(16) 0.0025(13) 0.0007(11) 0.0054(12) C25 0.0244(14) 0.0424(19) 0.0354(18) 0.0037(15) 0.0010(12) 0.0082(13) C26 0.0231(14) 0.051(2) 0.0312(17) -0.0073(14) 0.0011(12) 0.0090(13) C27 0.0217(14) 0.0382(19) 0.0381(18) 0.0141(15) 0.0031(12) 0.0028(13) C28 0.0379(16) 0.0314(17) 0.0397(19) 0.0052(15) 0.0049(13) 0.0003(13) C29 0.0296(14) 0.0337(17) 0.0341(17) 0.0078(14) 0.0040(12) 0.0013(13) C30 0.0440(18) 0.077(3) 0.039(2) -0.0065(18) 0.0020(14) 0.0094(17) C31 0.0353(16) 0.0279(16) 0.0369(18) -0.0023(13) 0.0005(13) 0.0081(13) C32 0.0416(17) 0.0328(17) 0.0406(19) -0.0075(14) 0.0074(14) 0.0091(14) C33 0.0457(17) 0.0300(17) 0.0246(16) -0.0066(13) 0.0048(13) -0.0004(14) C34 0.0388(16) 0.0213(15) 0.0260(16) 0.0047(12) -0.0007(12) -0.0031(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C10 1.360(3) . ? O1 C13 1.428(3) . ? O2 C14 1.206(3) . ? O3 C17 1.206(3) . ? O4 C27 1.387(3) . ? O4 C30 1.393(3) . ? O5 C31 1.206(3) . ? O6 C34 1.211(3) . ? N1 N2 1.305(3) . ? N1 C5 1.382(3) . ? N2 N3 1.358(3) . ? N3 C6 1.349(3) . ? N3 H1 0.89(3) . ? N4 N5 1.274(3) . ? N4 C1 1.407(3) . ? N5 C7 1.411(3) . ? N6 C17 1.396(3) . ? N6 C14 1.400(3) . ? N6 C2 1.428(3) . ? N7 N8 1.303(3) . ? N7 C22 1.379(3) . ? N8 N9 1.348(3) . ? N9 C23 1.358(3) . ? N9 H2 0.89(3) . ? N10 N11 1.275(3) . ? N10 C18 1.407(3) . ? N11 C24 1.414(3) . ? N12 C34 1.401(3) . ? N12 C31 1.403(3) . ? N12 C19 1.428(3) . ? C1 C2 1.394(3) . ? C1 C6 1.415(3) . ? C2 C3 1.403(3) . ? C3 C4 1.370(3) . ? C3 H3 0.9500 . ? C4 C5 1.403(3) . ? C4 H4 0.9500 . ? C5 C6 1.398(3) . ? C7 C12 1.386(3) . ? C7 C8 1.405(3) . ? C8 C9 1.370(3) . ? C8 H8 0.9500 . ? C9 C10 1.397(4) . ? C9 H9 0.9500 . ? C10 C11 1.387(3) . ? C11 C12 1.383(3) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C15 1.485(4) . ? C15 C16 1.318(4) . ? C15 H15 0.9500 . ? C16 C17 1.483(4) . ? C16 H16 0.9500 . ? C18 C19 1.391(3) . ? C18 C23 1.413(3) . ? C19 C20 1.406(3) . ? C20 C21 1.371(3) . ? C20 H20 0.9500 . ? C21 C22 1.398(3) . ? C21 H21 0.9500 . ? C22 C23 1.394(3) . ? C24 C25 1.389(4) . ? C24 C29 1.399(4) . ? C25 C26 1.401(4) . ? C25 H25 0.9500 . ? C26 C27 1.387(4) . ? C26 H26 0.9500 . ? C27 C28 1.378(4) . ? C28 C29 1.373(4) . ? C28 H28 0.9500 . ? C29 H29 0.9500 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C30 H30D 0.9800 . ? C30 H30E 0.9800 . ? C30 H30F 0.9800 . ? C31 C32 1.484(4) . ? C32 C33 1.322(4) . ? C32 H32 0.9500 . ? C33 C34 1.483(4) . ? C33 H33 0.9500 . ? 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 C10 O1 C13 117.5(2) . . ? C27 O4 C30 117.2(2) . . ? N2 N1 C5 108.0(2) . . ? N1 N2 N3 108.76(19) . . ? C6 N3 N2 110.6(2) . . ? C6 N3 H1 128.3(19) . . ? N2 N3 H1 120.7(19) . . ? N5 N4 C1 112.4(2) . . ? N4 N5 C7 114.9(2) . . ? C17 N6 C14 109.5(2) . . ? C17 N6 C2 124.8(2) . . ? C14 N6 C2 125.0(2) . . ? N8 N7 C22 107.8(2) . . ? N7 N8 N9 109.1(2) . . ? N8 N9 C23 110.5(2) . . ? N8 N9 H2 123(2) . . ? C23 N9 H2 126(2) . . ? N11 N10 C18 111.5(2) . . ? N10 N11 C24 116.1(2) . . ? C34 N12 C31 109.7(2) . . ? C34 N12 C19 125.7(2) . . ? C31 N12 C19 124.5(2) . . ? C2 C1 N4 118.6(2) . . ? C2 C1 C6 114.9(2) . . ? N4 C1 C6 126.5(2) . . ? C1 C2 C3 123.0(2) . . ? C1 C2 N6 117.9(2) . . ? C3 C2 N6 119.1(2) . . ? C4 C3 C2 121.4(2) . . ? C4 C3 H3 119.3 . . ? C2 C3 H3 119.3 . . ? C3 C4 C5 117.4(2) . . ? C3 C4 H4 121.3 . . ? C5 C4 H4 121.3 . . ? N1 C5 C6 108.3(2) . . ? N1 C5 C4 130.5(2) . . ? C6 C5 C4 121.2(2) . . ? N3 C6 C5 104.3(2) . . ? N3 C6 C1 133.6(2) . . ? C5 C6 C1 122.1(2) . . ? C12 C7 C8 119.0(2) . . ? C12 C7 N5 116.0(2) . . ? C8 C7 N5 125.1(2) . . ? C9 C8 C7 119.9(2) . . ? C9 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? C8 C9 C10 120.5(2) . . ? C8 C9 H9 119.7 . . ? C10 C9 H9 119.7 . . ? O1 C10 C11 124.6(2) . . ? O1 C10 C9 115.4(2) . . ? C11 C10 C9 120.0(2) . . ? C12 C11 C10 119.2(2) . . ? C12 C11 H11 120.4 . . ? C10 C11 H11 120.4 . . ? C11 C12 C7 121.4(2) . . ? C11 C12 H12 119.3 . . ? C7 C12 H12 119.3 . . ? O1 C13 H13A 109.5 . . ? O1 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O1 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O2 C14 N6 125.1(2) . . ? O2 C14 C15 128.6(2) . . ? N6 C14 C15 106.3(2) . . ? C16 C15 C14 108.6(2) . . ? C16 C15 H15 125.7 . . ? C14 C15 H15 125.7 . . ? C15 C16 C17 109.3(2) . . ? C15 C16 H16 125.3 . . ? C17 C16 H16 125.3 . . ? O3 C17 N6 124.3(2) . . ? O3 C17 C16 129.6(3) . . ? N6 C17 C16 106.1(2) . . ? C19 C18 N10 120.0(2) . . ? C19 C18 C23 114.5(2) . . ? N10 C18 C23 125.4(2) . . ? C18 C19 C20 123.2(2) . . ? C18 C19 N12 119.4(2) . . ? C20 C19 N12 117.4(2) . . ? C21 C20 C19 121.3(2) . . ? C21 C20 H20 119.3 . . ? C19 C20 H20 119.3 . . ? C20 C21 C22 117.2(2) . . ? C20 C21 H21 121.4 . . ? C22 C21 H21 121.4 . . ? N7 C22 C23 108.6(2) . . ? N7 C22 C21 130.0(2) . . ? C23 C22 C21 121.3(2) . . ? N9 C23 C22 103.9(2) . . ? N9 C23 C18 133.7(2) . . ? C22 C23 C18 122.4(2) . . ? C25 C24 C29 119.4(3) . . ? C25 C24 N11 125.3(3) . . ? C29 C24 N11 115.2(2) . . ? C24 C25 C26 119.9(3) . . ? C24 C25 H25 120.1 . . ? C26 C25 H25 120.1 . . ? C27 C26 C25 118.8(3) . . ? C27 C26 H26 120.6 . . ? C25 C26 H26 120.6 . . ? C28 C27 O4 115.0(3) . . ? C28 C27 C26 121.9(3) . . ? O4 C27 C26 123.1(3) . . ? C29 C28 C27 118.9(3) . . ? C29 C28 H28 120.5 . . ? C27 C28 H28 120.5 . . ? C28 C29 C24 121.1(3) . . ? C28 C29 H29 119.5 . . ? C24 C29 H29 119.5 . . ? O4 C30 H30A 109.5 . . ? O4 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? O4 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? O4 C30 H30D 109.5 . . ? H30A C30 H30D 141.1 . . ? H30B C30 H30D 56.3 . . ? H30C C30 H30D 56.3 . . ? O4 C30 H30E 109.5 . . ? H30A C30 H30E 56.3 . . ? H30B C30 H30E 141.1 . . ? H30C C30 H30E 56.3 . . ? H30D C30 H30E 109.5 . . ? O4 C30 H30F 109.5 . . ? H30A C30 H30F 56.3 . . ? H30B C30 H30F 56.3 . . ? H30C C30 H30F 141.1 . . ? H30D C30 H30F 109.5 . . ? H30E C30 H30F 109.5 . . ? O5 C31 N12 124.8(2) . . ? O5 C31 C32 129.2(3) . . ? N12 C31 C32 106.0(2) . . ? C33 C32 C31 109.1(2) . . ? C33 C32 H32 125.4 . . ? C31 C32 H32 125.4 . . ? C32 C33 C34 109.1(2) . . ? C32 C33 H33 125.5 . . ? C34 C33 H33 125.5 . . ? O6 C34 N12 125.2(2) . . ? O6 C34 C33 128.7(2) . . ? N12 C34 C33 106.1(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 N2 N3 -0.9(2) . . . . ? N1 N2 N3 C6 0.7(2) . . . . ? C1 N4 N5 C7 178.17(18) . . . . ? C22 N7 N8 N9 0.6(3) . . . . ? N7 N8 N9 C23 -0.1(3) . . . . ? C18 N10 N11 C24 -179.97(18) . . . . ? N5 N4 C1 C2 -176.80(19) . . . . ? N5 N4 C1 C6 0.9(3) . . . . ? N4 C1 C2 C3 175.0(2) . . . . ? C6 C1 C2 C3 -3.0(3) . . . . ? N4 C1 C2 N6 -4.7(3) . . . . ? C6 C1 C2 N6 177.30(19) . . . . ? C17 N6 C2 C1 101.2(3) . . . . ? C14 N6 C2 C1 -69.0(3) . . . . ? C17 N6 C2 C3 -78.5(3) . . . . ? C14 N6 C2 C3 111.3(3) . . . . ? C1 C2 C3 C4 1.0(3) . . . . ? N6 C2 C3 C4 -179.3(2) . . . . ? C2 C3 C4 C5 1.3(3) . . . . ? N2 N1 C5 C6 0.7(2) . . . . ? N2 N1 C5 C4 -178.1(2) . . . . ? C3 C4 C5 N1 177.3(2) . . . . ? C3 C4 C5 C6 -1.5(3) . . . . ? N2 N3 C6 C5 -0.2(2) . . . . ? N2 N3 C6 C1 179.0(2) . . . . ? N1 C5 C6 N3 -0.3(2) . . . . ? C4 C5 C6 N3 178.7(2) . . . . ? N1 C5 C6 C1 -179.63(19) . . . . ? C4 C5 C6 C1 -0.6(3) . . . . ? C2 C1 C6 N3 -176.3(2) . . . . ? N4 C1 C6 N3 5.9(4) . . . . ? C2 C1 C6 C5 2.8(3) . . . . ? N4 C1 C6 C5 -175.0(2) . . . . ? N4 N5 C7 C12 178.50(19) . . . . ? N4 N5 C7 C8 -2.1(3) . . . . ? C12 C7 C8 C9 -1.4(3) . . . . ? N5 C7 C8 C9 179.2(2) . . . . ? C7 C8 C9 C10 -0.6(4) . . . . ? C13 O1 C10 C11 -0.6(3) . . . . ? C13 O1 C10 C9 179.5(2) . . . . ? C8 C9 C10 O1 -177.9(2) . . . . ? C8 C9 C10 C11 2.2(4) . . . . ? O1 C10 C11 C12 178.3(2) . . . . ? C9 C10 C11 C12 -1.8(3) . . . . ? C10 C11 C12 C7 -0.2(3) . . . . ? C8 C7 C12 C11 1.8(3) . . . . ? N5 C7 C12 C11 -178.7(2) . . . . ? C17 N6 C14 O2 -177.3(2) . . . . ? C2 N6 C14 O2 -5.8(4) . . . . ? C17 N6 C14 C15 3.1(3) . . . . ? C2 N6 C14 C15 174.6(2) . . . . ? O2 C14 C15 C16 178.0(3) . . . . ? N6 C14 C15 C16 -2.3(3) . . . . ? C14 C15 C16 C17 0.7(3) . . . . ? C14 N6 C17 O3 177.0(3) . . . . ? C2 N6 C17 O3 5.5(4) . . . . ? C14 N6 C17 C16 -2.7(3) . . . . ? C2 N6 C17 C16 -174.2(2) . . . . ? C15 C16 C17 O3 -178.5(3) . . . . ? C15 C16 C17 N6 1.2(3) . . . . ? N11 N10 C18 C19 177.4(2) . . . . ? N11 N10 C18 C23 -1.7(3) . . . . ? N10 C18 C19 C20 -178.9(2) . . . . ? C23 C18 C19 C20 0.3(3) . . . . ? N10 C18 C19 N12 0.4(3) . . . . ? C23 C18 C19 N12 179.56(19) . . . . ? C34 N12 C19 C18 73.3(3) . . . . ? C31 N12 C19 C18 -111.2(3) . . . . ? C34 N12 C19 C20 -107.4(3) . . . . ? C31 N12 C19 C20 68.1(3) . . . . ? C18 C19 C20 C21 0.3(4) . . . . ? N12 C19 C20 C21 -178.9(2) . . . . ? C19 C20 C21 C22 0.0(3) . . . . ? N8 N7 C22 C23 -0.9(3) . . . . ? N8 N7 C22 C21 177.2(2) . . . . ? C20 C21 C22 N7 -179.0(2) . . . . ? C20 C21 C22 C23 -1.0(3) . . . . ? N8 N9 C23 C22 -0.4(3) . . . . ? N8 N9 C23 C18 -179.6(2) . . . . ? N7 C22 C23 N9 0.8(2) . . . . ? C21 C22 C23 N9 -177.5(2) . . . . ? N7 C22 C23 C18 -179.9(2) . . . . ? C21 C22 C23 C18 1.8(3) . . . . ? C19 C18 C23 N9 177.8(2) . . . . ? N10 C18 C23 N9 -3.1(4) . . . . ? C19 C18 C23 C22 -1.3(3) . . . . ? N10 C18 C23 C22 177.8(2) . . . . ? N10 N11 C24 C25 -6.0(3) . . . . ? N10 N11 C24 C29 176.0(2) . . . . ? C29 C24 C25 C26 1.0(3) . . . . ? N11 C24 C25 C26 -176.9(2) . . . . ? C24 C25 C26 C27 -0.3(4) . . . . ? C30 O4 C27 C28 173.1(2) . . . . ? C30 O4 C27 C26 -6.8(3) . . . . ? C25 C26 C27 C28 -0.9(4) . . . . ? C25 C26 C27 O4 179.0(2) . . . . ? O4 C27 C28 C29 -178.5(2) . . . . ? C26 C27 C28 C29 1.4(4) . . . . ? C27 C28 C29 C24 -0.7(4) . . . . ? C25 C24 C29 C28 -0.4(4) . . . . ? N11 C24 C29 C28 177.7(2) . . . . ? C34 N12 C31 O5 179.3(3) . . . . ? C19 N12 C31 O5 3.2(4) . . . . ? C34 N12 C31 C32 -0.4(3) . . . . ? C19 N12 C31 C32 -176.5(2) . . . . ? O5 C31 C32 C33 -179.4(3) . . . . ? N12 C31 C32 C33 0.3(3) . . . . ? C31 C32 C33 C34 -0.1(3) . . . . ? C31 N12 C34 O6 -178.9(3) . . . . ? C19 N12 C34 O6 -2.8(4) . . . . ? C31 N12 C34 C33 0.3(3) . . . . ? C19 N12 C34 C33 176.4(2) . . . . ? C32 C33 C34 O6 179.0(3) . . . . ? C32 C33 C34 N12 -0.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.952 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.952 _refine_diff_density_max 0.527 _refine_diff_density_min -0.256 _refine_diff_density_rms 0.052