# Electronic Supplementary Material (ESI) for Organic and Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr J Casado' _publ_contact_author_email jucali@usal.es _publ_section_title ; Aromatic C-Nitrosation of a Bioactive Molecule. Nitrosation of Minoxidil ; loop_ _publ_author_name Casado M.Gonzalez-Jimenez J.Arenas-Valganon E.Calle # Attachment 'MINRX03.cif' data_2fin _database_code_depnum_ccdc_archive 'CCDC 819626' #TrackingRef 'MINRX03.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H62 N24 O11' _chemical_formula_weight 1007.10 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.2884(3) _cell_length_b 13.6490(3) _cell_length_c 18.6062(5) _cell_angle_alpha 110.437(2) _cell_angle_beta 95.594(2) _cell_angle_gamma 91.674(2) _cell_volume 2431.07(11) _cell_formula_units_Z 2 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.376 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1068 _exptl_absorpt_coefficient_mu 0.886 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9880 _diffrn_reflns_av_R_equivalents 0.0211 _diffrn_reflns_av_sigmaI/netI 0.0281 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.55 _diffrn_reflns_theta_max 50.17 _reflns_number_total 4834 _reflns_number_gt 4285 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0647P)^2^+1.2950P] 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 4834 _refine_ls_number_parameters 663 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0463 _refine_ls_R_factor_gt 0.0414 _refine_ls_wR_factor_ref 0.1164 _refine_ls_wR_factor_gt 0.1096 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 O1 O 0.89431(16) 0.21507(13) -0.24827(10) 0.0448(5) Uani 1 1 d . . . O2 O 1.0530(2) 0.11222(18) -0.50617(12) 0.0738(6) Uani 1 1 d . . . N1 N 1.3411(2) 0.05435(18) -0.35676(12) 0.0479(6) Uani 1 1 d . . . N2 N 1.1476(3) 0.1024(2) -0.46065(15) 0.0602(7) Uani 1 1 d . . . N3 N 0.8997(2) 0.15378(18) -0.39858(13) 0.0525(6) Uani 1 1 d . . . H3A H 0.8310 0.1765 -0.3769 0.063 Uiso 1 1 calc R . . H3B H 0.8981 0.1348 -0.4479 0.063 Uiso 1 1 calc R . . N4 N 1.1065(2) 0.22328(16) -0.15801(12) 0.0456(6) Uani 1 1 d . . . H4A H 1.1721 0.2254 -0.1250 0.055 Uiso 1 1 calc R . . H4B H 1.0344 0.2484 -0.1423 0.055 Uiso 1 1 calc R . . N5 N 1.0046(2) 0.17843(15) -0.27995(12) 0.0363(5) Uani 1 1 d . . . N6 N 1.2261(2) 0.14226(15) -0.25827(12) 0.0371(5) Uani 1 1 d . . . C1 C 1.3612(4) -0.0119(3) -0.43621(18) 0.0770(11) Uani 1 1 d . . . H1A H 1.4329 0.0190 -0.4531 0.092 Uiso 1 1 calc R . . H1B H 1.2828 -0.0162 -0.4710 0.092 Uiso 1 1 calc R . . C2 C 1.3919(5) -0.1202(3) -0.4383(2) 0.0947(13) Uani 1 1 d . . . H2A H 1.3166 -0.1528 -0.4257 0.114 Uiso 1 1 calc R . . H2B H 1.4082 -0.1625 -0.4901 0.114 Uiso 1 1 calc R . . C3 C 1.5081(5) -0.1180(3) -0.3831(2) 0.1079(16) Uani 1 1 d . . . H3C H 1.5855 -0.0909 -0.3978 0.129 Uiso 1 1 calc R . . H3D H 1.5223 -0.1884 -0.3841 0.129 Uiso 1 1 calc R . . C4 C 1.4833(4) -0.0470(3) -0.3012(2) 0.0867(12) Uani 1 1 d . . . H4C H 1.4107 -0.0778 -0.2848 0.104 Uiso 1 1 calc R . . H4D H 1.5603 -0.0414 -0.2651 0.104 Uiso 1 1 calc R . . C5 C 1.4529(3) 0.0582(2) -0.30074(17) 0.0568(8) Uani 1 1 d . . . H5A H 1.4341 0.1010 -0.2495 0.068 Uiso 1 1 calc R . . H5B H 1.5289 0.0911 -0.3124 0.068 Uiso 1 1 calc R . . C6 C 1.2329(2) 0.10291(18) -0.33471(14) 0.0367(6) Uani 1 1 d . . . C7 C 1.1265(3) 0.11395(19) -0.38747(14) 0.0390(6) Uani 1 1 d . . . C8 C 1.0068(3) 0.14805(18) -0.35649(14) 0.0371(6) Uani 1 1 d . . . C9 C 1.1162(2) 0.18164(18) -0.23239(14) 0.0341(6) Uani 1 1 d . . . O3 O 0.48769(17) 0.61374(13) 0.09560(10) 0.0461(5) Uani 1 1 d . . . O4 O 0.3545(2) 0.76678(17) 0.35886(11) 0.0649(6) Uani 1 1 d . . . N7 N 0.7115(2) 0.63899(19) 0.37876(13) 0.0511(6) Uani 1 1 d . . . N8 N 0.4674(2) 0.73236(18) 0.36802(13) 0.0516(6) Uani 1 1 d . . . N9 N 0.3494(2) 0.69324(17) 0.20978(12) 0.0437(6) Uani 1 1 d . . . H9A H 0.3225 0.6844 0.1626 0.052 Uiso 1 1 calc R . . H9B H 0.2998 0.7199 0.2454 0.052 Uiso 1 1 calc R . . N10 N 0.7233(2) 0.55969(17) 0.12057(13) 0.0477(6) Uani 1 1 d . . . H10A H 0.8009 0.5390 0.1251 0.057 Uiso 1 1 calc R . . H10B H 0.6864 0.5553 0.0760 0.057 Uiso 1 1 calc R . . N11 N 0.53748(19) 0.62518(15) 0.16866(11) 0.0356(5) Uani 1 1 d . . . N12 N 0.7176(2) 0.60506(15) 0.25125(12) 0.0374(5) Uani 1 1 d . . . C10 C 0.6533(4) 0.6458(3) 0.44934(19) 0.0814(11) Uani 1 1 d . . . H10C H 0.5613 0.6584 0.4432 0.098 Uiso 1 1 calc R . . H10D H 0.6964 0.7042 0.4926 0.098 Uiso 1 1 calc R . . C11 C 0.6675(4) 0.5464(4) 0.4655(2) 0.0894(12) Uani 1 1 d . . . H11A H 0.6128 0.4905 0.4260 0.107 Uiso 1 1 calc R . . H11B H 0.6362 0.5551 0.5148 0.107 Uiso 1 1 calc R . . C12 C 0.8070(4) 0.5143(3) 0.4677(2) 0.0846(11) Uani 1 1 d . . . H12A H 0.8591 0.5629 0.5132 0.102 Uiso 1 1 calc R . . H12B H 0.8085 0.4450 0.4710 0.102 Uiso 1 1 calc R . . C13 C 0.8649(3) 0.5138(3) 0.39637(19) 0.0691(9) Uani 1 1 d . . . H13A H 0.9572 0.5012 0.4013 0.083 Uiso 1 1 calc R . . H13B H 0.8217 0.4573 0.3518 0.083 Uiso 1 1 calc R . . C14 C 0.8497(3) 0.6155(2) 0.38456(17) 0.0560(8) Uani 1 1 d . . . H14A H 0.8983 0.6711 0.4274 0.067 Uiso 1 1 calc R . . H14B H 0.8858 0.6126 0.3377 0.067 Uiso 1 1 calc R . . C15 C 0.6512(2) 0.64060(18) 0.31209(15) 0.0361(6) Uani 1 1 d . . . C16 C 0.5220(2) 0.67929(18) 0.30408(14) 0.0367(6) Uani 1 1 d . . . C17 C 0.4658(2) 0.66622(18) 0.22749(14) 0.0333(6) Uani 1 1 d . . . C18 C 0.6618(2) 0.59765(18) 0.18144(15) 0.0353(6) Uani 1 1 d . . . O5 O 1.01880(17) 0.47919(14) -0.12910(11) 0.0484(5) Uani 1 1 d . . . O6 O 0.7311(3) 0.47656(19) -0.36032(14) 0.0866(8) Uani 1 1 d . . . N13 N 0.8964(3) 0.77884(19) -0.24861(15) 0.0643(7) Uani 1 1 d . . . N14 N 0.7734(3) 0.5711(2) -0.32496(16) 0.0690(8) Uani 1 1 d . . . C19 C 0.8739(5) 0.7649(3) -0.3310(2) 0.0961(14) Uani 1 1 d . . . H19A H 0.8409 0.6933 -0.3607 0.115 Uiso 1 1 calc R . . H19B H 0.8090 0.8115 -0.3387 0.115 Uiso 1 1 calc R . . C20 C 0.9970(5) 0.7879(3) -0.3574(2) 0.1027(16) Uani 1 1 d . . . H20A H 0.9812 0.7804 -0.4114 0.123 Uiso 1 1 calc R . . H20B H 1.0594 0.7378 -0.3531 0.123 Uiso 1 1 calc R . . C21 C 1.0544(5) 0.8972(3) -0.3110(2) 0.1014(15) Uani 1 1 d . . . H21A H 1.1387 0.9082 -0.3272 0.122 Uiso 1 1 calc R . . H21B H 0.9971 0.9479 -0.3200 0.122 Uiso 1 1 calc R . . C22 C 1.0708(5) 0.9128(3) -0.2272(2) 0.0947(14) Uani 1 1 d . . . H22A H 1.0996 0.9853 -0.1975 0.114 Uiso 1 1 calc R . . H22B H 1.1375 0.8690 -0.2172 0.114 Uiso 1 1 calc R . . C23 C 0.9453(5) 0.8859(3) -0.2021(2) 0.0960(15) Uani 1 1 d . . . H23A H 0.9593 0.8931 -0.1481 0.115 Uiso 1 1 calc R . . H23B H 0.8809 0.9341 -0.2074 0.115 Uiso 1 1 calc R . . C24 C 0.9131(3) 0.7011(2) -0.22068(17) 0.0478(7) Uani 1 1 d . . . C25 C 0.8653(3) 0.5938(2) -0.26311(16) 0.0451(7) Uani 1 1 d . . . C26 C 0.9085(2) 0.5180(2) -0.23046(15) 0.0392(7) Uani 1 1 d . . . C27 C 1.0032(3) 0.6554(2) -0.11987(16) 0.0427(7) Uani 1 1 d . . . O7 O 0.69457(16) 0.76424(12) 0.04402(10) 0.0436(5) Uani 1 1 d . . . O8 O 0.8673(2) 1.06354(17) -0.01919(13) 0.0666(6) Uani 1 1 d . . . N15 N 1.0604(2) 0.68225(18) -0.04813(14) 0.0562(7) Uani 1 1 d . . . H15A H 1.0795 0.7473 -0.0208 0.067 Uiso 1 1 calc R . . H15B H 1.0786 0.6347 -0.0289 0.067 Uiso 1 1 calc R . . N16 N 0.8809(2) 0.41684(17) -0.26521(13) 0.0493(6) Uani 1 1 d . . . H16A H 0.9078 0.3740 -0.2433 0.059 Uiso 1 1 calc R . . H16B H 0.8359 0.3934 -0.3099 0.059 Uiso 1 1 calc R . . N17 N 0.9792(2) 0.55070(16) -0.16057(13) 0.0401(5) Uani 1 1 d . . . N18 N 0.9757(2) 0.72819(17) -0.14904(14) 0.0500(6) Uani 1 1 d . . . N19 N 0.5563(2) 1.16412(17) 0.10971(14) 0.0537(6) Uani 1 1 d . . . N20 N 0.7676(2) 1.09479(19) 0.01698(15) 0.0551(6) Uani 1 1 d . . . N21 N 0.4732(2) 0.82788(16) 0.09804(12) 0.0434(6) Uani 1 1 d . . . H21C H 0.4007 0.8453 0.1170 0.052 Uiso 1 1 calc R . . H21D H 0.4956 0.7645 0.0870 0.052 Uiso 1 1 calc R . . N22 N 0.8460(2) 0.88621(18) 0.00463(13) 0.0514(6) Uani 1 1 d . . . H22C H 0.8601 0.8221 -0.0018 0.062 Uiso 1 1 calc R . . H22D H 0.8998 0.9233 -0.0097 0.062 Uiso 1 1 calc R . . N23 N 0.66397(19) 0.86398(15) 0.05680(11) 0.0343(5) Uani 1 1 d . . . N24 N 0.51678(19) 0.99616(16) 0.10265(11) 0.0375(5) Uani 1 1 d . . . C28 C 0.6355(5) 1.2583(3) 0.1132(2) 0.0972(14) Uani 1 1 d . . . H28A H 0.7178 1.2376 0.0928 0.117 Uiso 1 1 calc R . . H28B H 0.5891 1.2921 0.0813 0.117 Uiso 1 1 calc R . . C29 C 0.6620(4) 1.3329(2) 0.1928(2) 0.0806(11) Uani 1 1 d . . . H29A H 0.7098 1.3952 0.1928 0.097 Uiso 1 1 calc R . . H29B H 0.7168 1.3015 0.2232 0.097 Uiso 1 1 calc R . . C30 C 0.5399(4) 1.3635(2) 0.2295(2) 0.0762(10) Uani 1 1 d . . . H30A H 0.4891 1.4023 0.2031 0.091 Uiso 1 1 calc R . . H30B H 0.5617 1.4082 0.2831 0.091 Uiso 1 1 calc R . . C31 C 0.4602(4) 1.2653(3) 0.2246(2) 0.0758(10) Uani 1 1 d . . . H31A H 0.5075 1.2311 0.2559 0.091 Uiso 1 1 calc R . . H31B H 0.3777 1.2846 0.2450 0.091 Uiso 1 1 calc R . . C32 C 0.4345(3) 1.1915(2) 0.14381(19) 0.0614(9) Uani 1 1 d . . . H32A H 0.3870 1.1284 0.1426 0.074 Uiso 1 1 calc R . . H32B H 0.3802 1.2234 0.1136 0.074 Uiso 1 1 calc R . . C33 C 0.5940(2) 1.06566(19) 0.08746(14) 0.0366(6) Uani 1 1 d . . . C34 C 0.7081(2) 1.03255(19) 0.04819(14) 0.0364(6) Uani 1 1 d . . . C35 C 0.7427(2) 0.92745(19) 0.03621(13) 0.0357(6) Uani 1 1 d . . . C36 C 0.5494(2) 0.89787(19) 0.08602(13) 0.0330(6) Uani 1 1 d . . . O9 O 0.3318(3) 0.4377(2) 0.0563(2) 0.1079(12) Uani 1 1 d . . . O10 O 0.2265(3) 0.8833(3) 0.1583(2) 0.0834(8) Uani 1 1 d . . . O11 O 0.8409(3) 0.4080(2) -0.05913(14) 0.0679(6) Uani 1 1 d . . . H33A H 0.348(5) 0.387(4) 0.034(3) 0.105(18) Uiso 1 1 d . . . H33B H 0.407(8) 0.488(6) 0.061(4) 0.240 Uiso 1 1 d . . . H34A H 0.905(4) 0.430(3) -0.084(3) 0.108(15) Uiso 1 1 d . . . H34B H 0.793(4) 0.462(3) -0.0499(19) 0.070(12) Uiso 1 1 d . . . H35A H 0.178(5) 0.855(3) 0.191(3) 0.117(15) Uiso 1 1 d . . . H35B H 0.198(3) 0.821(2) 0.1220(15) 0.035(8) Uiso 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 O1 0.0367(11) 0.0497(11) 0.0505(11) 0.0186(9) 0.0100(9) 0.0133(8) O2 0.0879(16) 0.0957(17) 0.0443(12) 0.0318(12) 0.0041(12) 0.0309(13) N1 0.0411(14) 0.0589(14) 0.0381(13) 0.0092(11) 0.0052(11) 0.0114(12) N2 0.0691(18) 0.0701(17) 0.0465(16) 0.0255(13) 0.0088(14) 0.0178(13) N3 0.0490(15) 0.0630(15) 0.0392(13) 0.0116(11) -0.0033(12) 0.0163(12) N4 0.0439(13) 0.0514(14) 0.0384(15) 0.0118(11) 0.0027(10) 0.0133(11) N5 0.0342(13) 0.0340(12) 0.0405(14) 0.0127(10) 0.0032(11) 0.0057(9) N6 0.0381(13) 0.0333(11) 0.0371(14) 0.0091(10) 0.0036(10) 0.0040(10) C1 0.072(2) 0.110(3) 0.0438(19) 0.0170(19) 0.0139(16) 0.041(2) C2 0.125(3) 0.089(3) 0.049(2) -0.0045(19) 0.014(2) 0.038(3) C3 0.164(4) 0.096(3) 0.056(2) 0.014(2) 0.007(3) 0.076(3) C4 0.110(3) 0.081(3) 0.064(2) 0.0196(19) 0.003(2) 0.033(2) C5 0.0397(17) 0.071(2) 0.0539(18) 0.0146(15) 0.0024(14) 0.0130(14) C6 0.0384(16) 0.0328(14) 0.0379(17) 0.0115(12) 0.0044(13) -0.0003(12) C7 0.0476(17) 0.0384(15) 0.0310(16) 0.0120(12) 0.0047(13) 0.0035(12) C8 0.0438(17) 0.0326(14) 0.0341(17) 0.0118(12) -0.0001(13) 0.0048(12) C9 0.0410(17) 0.0253(13) 0.0363(17) 0.0114(12) 0.0034(13) 0.0021(12) O3 0.0467(11) 0.0517(11) 0.0384(11) 0.0152(8) 0.0004(9) 0.0063(8) O4 0.0494(13) 0.0876(15) 0.0541(13) 0.0173(11) 0.0108(10) 0.0292(11) N7 0.0444(14) 0.0696(16) 0.0433(15) 0.0238(12) 0.0053(11) 0.0175(12) N8 0.0429(15) 0.0613(15) 0.0485(15) 0.0156(12) 0.0053(12) 0.0163(12) N9 0.0344(14) 0.0555(14) 0.0411(13) 0.0169(11) 0.0027(10) 0.0071(11) N10 0.0454(13) 0.0598(15) 0.0424(14) 0.0213(11) 0.0096(12) 0.0189(11) N11 0.0348(13) 0.0367(12) 0.0344(13) 0.0125(10) 0.0001(11) 0.0036(10) N12 0.0369(12) 0.0367(12) 0.0404(14) 0.0152(10) 0.0059(11) 0.0065(9) C10 0.075(2) 0.134(3) 0.047(2) 0.040(2) 0.0178(17) 0.050(2) C11 0.082(3) 0.142(4) 0.069(2) 0.066(3) 0.0093(19) 0.013(2) C12 0.098(3) 0.092(3) 0.079(3) 0.049(2) 0.005(2) 0.024(2) C13 0.071(2) 0.074(2) 0.061(2) 0.0217(17) -0.0006(17) 0.0265(17) C14 0.0433(18) 0.075(2) 0.0491(18) 0.0223(15) -0.0021(14) 0.0126(15) C15 0.0344(15) 0.0336(14) 0.0401(17) 0.0136(12) 0.0009(14) 0.0028(11) C16 0.0348(15) 0.0349(14) 0.0378(16) 0.0090(12) 0.0066(13) 0.0026(12) C17 0.0303(15) 0.0280(13) 0.0408(16) 0.0114(11) 0.0036(13) 0.0023(11) C18 0.0386(16) 0.0286(14) 0.0405(17) 0.0140(12) 0.0055(14) 0.0034(12) O5 0.0444(11) 0.0488(11) 0.0627(12) 0.0317(10) 0.0083(9) 0.0115(9) O6 0.116(2) 0.0606(16) 0.0762(16) 0.0274(13) -0.0283(14) -0.0128(14) N13 0.086(2) 0.0463(16) 0.0694(18) 0.0305(14) 0.0116(14) 0.0069(13) N14 0.089(2) 0.0559(18) 0.0640(18) 0.0279(14) -0.0076(16) 0.0028(15) C19 0.129(4) 0.077(3) 0.090(3) 0.058(2) -0.045(3) -0.032(2) C20 0.185(5) 0.071(3) 0.053(2) 0.0299(19) 0.002(3) -0.030(3) C21 0.148(4) 0.082(3) 0.075(3) 0.039(2) -0.008(3) -0.047(3) C22 0.151(4) 0.056(2) 0.071(3) 0.0282(19) -0.026(3) -0.037(2) C23 0.188(5) 0.040(2) 0.068(2) 0.0225(18) 0.032(3) 0.027(2) C24 0.0560(18) 0.0409(18) 0.056(2) 0.0257(15) 0.0156(15) 0.0115(13) C25 0.0481(17) 0.0448(17) 0.0475(17) 0.0220(14) 0.0072(14) 0.0074(13) C26 0.0364(15) 0.0399(18) 0.0458(17) 0.0183(14) 0.0129(13) 0.0073(12) C27 0.0430(16) 0.0444(19) 0.0447(18) 0.0185(15) 0.0133(14) 0.0036(13) O7 0.0435(10) 0.0328(10) 0.0492(11) 0.0084(8) 0.0017(8) 0.0071(8) O8 0.0478(13) 0.0821(15) 0.0867(16) 0.0455(12) 0.0262(12) 0.0072(11) N15 0.0712(17) 0.0466(14) 0.0512(17) 0.0187(12) 0.0067(13) -0.0032(12) N16 0.0575(15) 0.0394(15) 0.0527(14) 0.0192(12) 0.0037(11) 0.0040(11) N17 0.0408(13) 0.0367(14) 0.0493(15) 0.0216(12) 0.0096(11) 0.0071(10) N18 0.0663(16) 0.0390(13) 0.0484(16) 0.0183(12) 0.0132(13) 0.0047(11) N19 0.0632(16) 0.0333(14) 0.0601(15) 0.0083(11) 0.0174(13) 0.0017(12) N20 0.0453(15) 0.0589(15) 0.0686(16) 0.0303(13) 0.0127(13) 0.0029(12) N21 0.0379(12) 0.0403(13) 0.0539(14) 0.0171(11) 0.0126(10) 0.0052(11) N22 0.0415(14) 0.0514(14) 0.0600(15) 0.0155(12) 0.0156(12) 0.0043(11) N23 0.0329(12) 0.0312(12) 0.0350(12) 0.0071(9) 0.0028(10) 0.0033(10) N24 0.0350(12) 0.0347(13) 0.0390(12) 0.0082(10) 0.0046(9) 0.0012(10) C28 0.140(4) 0.042(2) 0.109(3) 0.013(2) 0.067(3) -0.007(2) C29 0.077(2) 0.0407(19) 0.114(3) 0.014(2) 0.015(2) -0.0033(17) C30 0.092(3) 0.0466(19) 0.071(2) -0.0019(16) 0.008(2) -0.0012(18) C31 0.083(2) 0.064(2) 0.077(2) 0.0137(19) 0.031(2) 0.0148(18) C32 0.0488(19) 0.0404(17) 0.084(2) 0.0083(16) 0.0050(17) 0.0096(14) C33 0.0396(16) 0.0329(16) 0.0311(14) 0.0053(12) -0.0010(12) 0.0004(13) C34 0.0358(15) 0.0379(15) 0.0331(14) 0.0111(12) 0.0007(12) -0.0034(12) C35 0.0314(15) 0.0409(16) 0.0294(14) 0.0065(12) 0.0020(12) -0.0010(13) C36 0.0325(15) 0.0351(16) 0.0270(13) 0.0075(11) -0.0028(11) -0.0007(13) O9 0.087(2) 0.0550(17) 0.138(3) -0.0212(18) 0.0166(18) 0.0025(14) O10 0.0691(16) 0.096(2) 0.113(2) 0.064(2) 0.0366(16) 0.0242(15) O11 0.0621(15) 0.0923(18) 0.0638(15) 0.0451(14) 0.0091(12) 0.0077(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 N5 1.358(3) . ? O2 N2 1.269(3) . ? N1 C6 1.337(3) . ? N1 C5 1.462(4) . ? N1 C1 1.478(4) . ? N2 C7 1.355(4) . ? N3 C8 1.308(3) . ? N4 C9 1.315(3) . ? N5 C8 1.340(3) . ? N5 C9 1.369(3) . ? N6 C9 1.326(3) . ? N6 C6 1.343(3) . ? C1 C2 1.508(5) . ? C2 C3 1.490(6) . ? C3 C4 1.545(5) . ? C4 C5 1.477(5) . ? C6 C7 1.445(4) . ? C7 C8 1.432(4) . ? O3 N11 1.359(3) . ? O4 N8 1.284(3) . ? N7 C15 1.339(3) . ? N7 C14 1.468(4) . ? N7 C10 1.471(4) . ? N8 C16 1.344(3) . ? N9 C17 1.308(3) . ? N10 C18 1.305(3) . ? N11 C17 1.345(3) . ? N11 C18 1.365(3) . ? N12 C15 1.330(3) . ? N12 C18 1.336(3) . ? C10 C11 1.498(6) . ? C11 C12 1.514(5) . ? C12 C13 1.505(5) . ? C13 C14 1.489(5) . ? C15 C16 1.458(4) . ? C16 C17 1.433(4) . ? O5 N17 1.356(3) . ? O6 N14 1.268(3) . ? N13 C24 1.343(4) . ? N13 C23 1.459(4) . ? N13 C19 1.471(5) . ? N14 C25 1.355(4) . ? C19 C20 1.467(6) . ? C20 C21 1.507(5) . ? C21 C22 1.490(5) . ? C22 C23 1.493(6) . ? C24 N18 1.342(4) . ? C24 C25 1.445(4) . ? C25 C26 1.432(4) . ? C26 N16 1.312(3) . ? C26 N17 1.345(3) . ? C27 N18 1.314(3) . ? C27 N15 1.325(3) . ? C27 N17 1.365(3) . ? O7 N23 1.350(3) . ? O8 N20 1.283(3) . ? N19 C33 1.342(3) . ? N19 C32 1.459(4) . ? N19 C28 1.481(4) . ? N20 C34 1.348(3) . ? N21 C36 1.310(3) . ? N22 C35 1.311(3) . ? N23 C35 1.343(3) . ? N23 C36 1.371(3) . ? N24 C36 1.328(3) . ? N24 C33 1.341(3) . ? C28 C29 1.468(5) . ? C29 C30 1.489(5) . ? C30 C31 1.521(5) . ? C31 C32 1.481(4) . ? C33 C34 1.444(4) . ? C34 C35 1.434(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 C6 N1 C5 121.5(2) . . ? C6 N1 C1 126.2(2) . . ? C5 N1 C1 112.3(2) . . ? O2 N2 C7 118.5(2) . . ? C8 N5 O1 120.0(2) . . ? C8 N5 C9 120.5(2) . . ? O1 N5 C9 119.2(2) . . ? C9 N6 C6 119.4(2) . . ? N1 C1 C2 109.6(3) . . ? C3 C2 C1 112.2(3) . . ? C2 C3 C4 108.8(3) . . ? C5 C4 C3 110.0(3) . . ? N1 C5 C4 112.2(3) . . ? N1 C6 N6 116.0(2) . . ? N1 C6 C7 124.1(2) . . ? N6 C6 C7 119.8(2) . . ? N2 C7 C8 123.0(2) . . ? N2 C7 C6 119.4(2) . . ? C8 C7 C6 117.2(2) . . ? N3 C8 N5 117.9(2) . . ? N3 C8 C7 123.7(2) . . ? N5 C8 C7 118.4(2) . . ? N4 C9 N6 121.4(2) . . ? N4 C9 N5 115.4(2) . . ? N6 C9 N5 123.2(2) . . ? C15 N7 C14 120.3(2) . . ? C15 N7 C10 128.1(2) . . ? C14 N7 C10 111.2(2) . . ? O4 N8 C16 117.5(2) . . ? C17 N11 O3 119.9(2) . . ? C17 N11 C18 121.0(2) . . ? O3 N11 C18 119.2(2) . . ? C15 N12 C18 119.8(2) . . ? N7 C10 C11 110.4(3) . . ? C10 C11 C12 113.3(3) . . ? C13 C12 C11 110.4(3) . . ? C14 C13 C12 110.9(3) . . ? N7 C14 C13 111.4(3) . . ? N12 C15 N7 115.7(2) . . ? N12 C15 C16 120.3(2) . . ? N7 C15 C16 124.0(2) . . ? N8 C16 C17 123.6(2) . . ? N8 C16 C15 119.1(2) . . ? C17 C16 C15 117.0(2) . . ? N9 C17 N11 116.5(2) . . ? N9 C17 C16 125.0(2) . . ? N11 C17 C16 118.6(2) . . ? N10 C18 N12 120.9(2) . . ? N10 C18 N11 116.1(2) . . ? N12 C18 N11 123.0(2) . . ? C24 N13 C23 120.4(3) . . ? C24 N13 C19 125.1(3) . . ? C23 N13 C19 111.2(3) . . ? O6 N14 C25 118.8(2) . . ? C20 C19 N13 109.6(3) . . ? C19 C20 C21 111.6(4) . . ? C22 C21 C20 110.1(3) . . ? C21 C22 C23 111.0(4) . . ? N13 C23 C22 110.5(3) . . ? N18 C24 N13 116.4(3) . . ? N18 C24 C25 120.4(2) . . ? N13 C24 C25 123.2(3) . . ? N14 C25 C26 123.4(2) . . ? N14 C25 C24 120.0(2) . . ? C26 C25 C24 116.1(2) . . ? N16 C26 N17 117.7(2) . . ? N16 C26 C25 123.0(3) . . ? N17 C26 C25 119.3(2) . . ? N18 C27 N15 119.9(2) . . ? N18 C27 N17 123.3(3) . . ? N15 C27 N17 116.8(2) . . ? C26 N17 O5 119.4(2) . . ? C26 N17 C27 120.0(2) . . ? O5 N17 C27 120.5(2) . . ? C27 N18 C24 119.8(2) . . ? C33 N19 C32 121.6(2) . . ? C33 N19 C28 126.2(3) . . ? C32 N19 C28 111.7(2) . . ? O8 N20 C34 119.4(2) . . ? C35 N23 O7 119.3(2) . . ? C35 N23 C36 120.4(2) . . ? O7 N23 C36 120.09(19) . . ? C36 N24 C33 120.1(2) . . ? C29 C28 N19 111.1(3) . . ? C28 C29 C30 112.4(3) . . ? C29 C30 C31 109.2(3) . . ? C32 C31 C30 111.1(3) . . ? N19 C32 C31 111.1(3) . . ? N24 C33 N19 115.8(2) . . ? N24 C33 C34 120.2(2) . . ? N19 C33 C34 124.0(2) . . ? N20 C34 C35 122.8(2) . . ? N20 C34 C33 120.0(2) . . ? C35 C34 C33 116.8(2) . . ? N22 C35 N23 116.1(2) . . ? N22 C35 C34 124.8(2) . . ? N23 C35 C34 119.1(2) . . ? N21 C36 N24 121.1(2) . . ? N21 C36 N23 116.2(2) . . ? N24 C36 N23 122.7(2) . . ? _diffrn_measured_fraction_theta_max 0.959 _diffrn_reflns_theta_full 50.17 _diffrn_measured_fraction_theta_full 0.959 _refine_diff_density_max 0.288 _refine_diff_density_min -0.205 _refine_diff_density_rms 0.038