Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name D.Tocher 'Sarah Barnett' 'Martin Vickers' _publ_contact_author_name 'Derek Tocher' _publ_contact_author_address ; Department of Chemistry University College London 20 Gordon Street London WC1H 0AJ UNITED KINGDOM ; _publ_contact_author_email D.A.TOCHER@UCL.AC.UK _publ_requested_journal 'Cryst Eng. Comm.' _publ_section_title ; The solvates of o-acetamidobenzamide ; # Attachment 'BarnettTocherAABAsolvates.cif' data_[(AABA)6.(CHCl3)] _database_code_depnum_ccdc_archive 'CCDC 294939' _audit_creation_method SHELXL-97 _chemical_name_systematic ; o-Acetamidobenzamide Chloroform (6/1) ; _chemical_name_common (C9H10N2O2)6.(CHCl3) _chemical_melting_point ? _chemical_formula_moiety 'C9.17 H10.17 Cl0.50 N2 O2' _chemical_formula_sum 'C9.17 H10.17 Cl0.50 N2 O2' _chemical_formula_weight 198.08 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Hexagonal _symmetry_space_group_name_H-M P6(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+1/3' '-x+y, -x, z+2/3' '-x, -y, z+1/2' 'y, -x+y, z+5/6' 'x-y, x, z+1/6' _cell_length_a 21.910(2) _cell_length_b 21.910 _cell_length_c 20.559(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 8546.8(12) _cell_formula_units_Z 36 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 15169 _cell_measurement_theta_min 2.254 _cell_measurement_theta_max 28.012 _exptl_crystal_description 'Hexagonal Bipyramidal' _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.59 _exptl_crystal_size_min 0.50 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.385 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3732 _exptl_absorpt_coefficient_mu 0.234 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8612 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS v2.03' _exptl_special_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 SMART APEX diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% None _diffrn_reflns_number 76405 _diffrn_reflns_av_R_equivalents 0.0435 _diffrn_reflns_av_sigmaI/netI 0.0359 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.46 _diffrn_reflns_theta_max 28.31 _reflns_number_total 7219 _reflns_number_gt 11192 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _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^)+(0.0813P)^2^+3.8700P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary 'direct methods' _atom_sites_solution_secondary 'difference Fourier synthesis' _atom_sites_solution_hydrogens 'found from delta-F; solvent H geometrically placed' _refine_ls_hydrogen_treatment 'rigid rotor model for methyls; solvent H riding; others freely refined' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.04(7) _refine_ls_number_reflns 13800 _refine_ls_number_parameters 913 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0766 _refine_ls_R_factor_gt 0.0583 _refine_ls_wR_factor_ref 0.1541 _refine_ls_wR_factor_gt 0.1406 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.02564(13) 0.03915(12) 0.23305(12) 0.0215(5) Uani 1 1 d . . . C2 C 0.09512(13) 0.09500(13) 0.22536(13) 0.0221(5) Uani 1 1 d . . . C3 C 0.15012(14) 0.08090(14) 0.23252(15) 0.0301(6) Uani 1 1 d . . . H3 H 0.1947(19) 0.1167(18) 0.2325(17) 0.033(8) Uiso 1 1 d . . . C4 C 0.13770(16) 0.01435(15) 0.24690(17) 0.0346(6) Uani 1 1 d . . . H4 H 0.178(2) 0.0097(19) 0.2476(19) 0.049(10) Uiso 1 1 d . . . C5 C 0.06929(15) -0.04022(14) 0.25334(15) 0.0307(6) Uani 1 1 d . . . H5 H 0.0608(15) -0.0875(15) 0.2625(13) 0.017(6) Uiso 1 1 d . . . C6 C 0.01357(14) -0.02830(13) 0.24715(14) 0.0271(5) Uani 1 1 d . . . H6 H -0.0318(16) -0.0655(15) 0.2549(14) 0.020(7) Uiso 1 1 d . . . C7 C 0.11166(13) 0.16866(13) 0.20978(14) 0.0251(5) Uani 1 1 d . . . O1 O 0.06542(10) 0.18600(9) 0.21301(11) 0.0336(5) Uani 1 1 d . . . N1 N 0.17665(12) 0.21539(12) 0.19197(14) 0.0329(6) Uani 1 1 d . . . H1A H 0.1869(16) 0.2583(17) 0.1841(16) 0.026(8) Uiso 1 1 d . . . H1B H 0.2061(18) 0.2040(17) 0.1876(16) 0.032(9) Uiso 1 1 d . . . C8 C -0.10075(13) 0.00690(13) 0.22335(14) 0.0264(5) Uani 1 1 d . . . C9 C -0.14447(14) 0.04168(15) 0.21383(17) 0.0350(6) Uani 1 1 d . . . H9A H -0.1566 0.0398 0.1677 0.052 Uiso 1 1 calc R . . H9B H -0.1175 0.0909 0.2279 0.052 Uiso 1 1 calc R . . H9C H -0.1877 0.0169 0.2397 0.052 Uiso 1 1 calc R . . O2 O -0.12779(10) -0.05679(10) 0.22756(12) 0.0376(5) Uani 1 1 d . . . N2 N -0.03058(11) 0.05276(12) 0.22656(12) 0.0261(5) Uani 1 1 d . . . H2 H -0.0184(18) 0.0938(19) 0.2223(16) 0.030(8) Uiso 1 1 d . . . C11 C 0.65765(13) 0.89804(13) 0.02797(13) 0.0254(5) Uani 1 1 d . . . C12 C 0.72790(13) 0.95318(13) 0.03616(13) 0.0242(5) Uani 1 1 d . . . C13 C 0.77953(15) 0.93524(15) 0.04870(15) 0.0304(6) Uani 1 1 d . . . H13 H 0.8231(19) 0.9667(18) 0.0595(17) 0.036(9) Uiso 1 1 d . . . C14 C 0.76354(17) 0.86598(16) 0.05369(16) 0.0364(7) Uani 1 1 d . . . H14 H 0.8021(19) 0.8583(19) 0.0676(17) 0.040(9) Uiso 1 1 d . . . C15 C 0.69448(17) 0.81309(16) 0.04686(17) 0.0363(7) Uani 1 1 d . . . H15 H 0.679(2) 0.768(2) 0.053(2) 0.065(13) Uiso 1 1 d . . . C16 C 0.64241(16) 0.82842(15) 0.03470(15) 0.0319(6) Uani 1 1 d . . . H16 H 0.5992(18) 0.7920(19) 0.0262(16) 0.032(8) Uiso 1 1 d . . . C17 C 0.74711(13) 1.02884(13) 0.03222(13) 0.0251(5) Uani 1 1 d . . . O11 O 0.70198(10) 1.04593(10) 0.02125(12) 0.0380(5) Uani 1 1 d . . . N11 N 0.81378(12) 1.07856(13) 0.04167(13) 0.0286(5) Uani 1 1 d . . . H11A H 0.823(2) 1.117(2) 0.038(2) 0.062(13) Uiso 1 1 d . . . H11B H 0.8450(17) 1.0711(16) 0.0440(15) 0.022(8) Uiso 1 1 d . . . C18 C 0.53789(14) 0.87235(14) -0.00545(16) 0.0317(6) Uani 1 1 d . . . C19 C 0.49918(16) 0.91089(17) -0.0219(2) 0.0430(8) Uani 1 1 d . . . H19A H 0.5137 0.9323 -0.0651 0.065 Uiso 1 1 calc R . . H19B H 0.5103 0.9478 0.0104 0.065 Uiso 1 1 calc R . . H19C H 0.4483 0.8777 -0.0219 0.065 Uiso 1 1 calc R . . O12 O 0.50978(11) 0.80871(11) -0.00994(15) 0.0511(7) Uani 1 1 d . . . N12 N 0.60507(12) 0.91450(12) 0.01413(13) 0.0291(5) Uani 1 1 d . . . H12 H 0.623(2) 0.957(2) 0.011(2) 0.045(10) Uiso 1 1 d . . . C21 C 0.47451(13) 0.87294(13) 0.32356(14) 0.0255(5) Uani 1 1 d . . . C22 C 0.40494(13) 0.81583(12) 0.31668(14) 0.0248(5) Uani 1 1 d . . . C23 C 0.35136(14) 0.83109(14) 0.30647(17) 0.0336(6) Uani 1 1 d . . . H23 H 0.3047(18) 0.7924(17) 0.2951(16) 0.032(8) Uiso 1 1 d . . . C24 C 0.36336(15) 0.89884(15) 0.30444(18) 0.0377(7) Uani 1 1 d . . . H24 H 0.325(2) 0.9053(18) 0.2986(17) 0.041(9) Uiso 1 1 d . . . C25 C 0.43108(15) 0.95411(15) 0.31152(18) 0.0376(7) Uani 1 1 d . . . H25 H 0.4369(19) 0.998(2) 0.3161(18) 0.044(10) Uiso 1 1 d . . . C26 C 0.48656(15) 0.94176(14) 0.32108(16) 0.0331(6) Uani 1 1 d . . . H26 H 0.5324(19) 0.9768(18) 0.3298(17) 0.037(9) Uiso 1 1 d . . . C27 C 0.38886(14) 0.74069(13) 0.31901(15) 0.0282(6) Uani 1 1 d . . . O21 O 0.43650(10) 0.72570(9) 0.31986(12) 0.0374(5) Uani 1 1 d . . . N21 N 0.32187(13) 0.69066(13) 0.32079(16) 0.0377(7) Uani 1 1 d . . . H21A H 0.3155(19) 0.653(2) 0.3166(18) 0.043(10) Uiso 1 1 d . . . H21B H 0.284(2) 0.6946(19) 0.3230(18) 0.043(10) Uiso 1 1 d . . . C28 C 0.59878(14) 0.90334(14) 0.34472(15) 0.0309(6) Uani 1 1 d . . . C29 C 0.64359(15) 0.86909(16) 0.34829(18) 0.0374(7) Uani 1 1 d . . . H29A H 0.6646 0.8715 0.3056 0.056 Uiso 1 1 calc R . . H29B H 0.6143 0.8196 0.3612 0.056 Uiso 1 1 calc R . . H29C H 0.6811 0.8938 0.3804 0.056 Uiso 1 1 calc R . . O22 O 0.62415(11) 0.96681(10) 0.35269(15) 0.0486(6) Uani 1 1 d . . . N22 N 0.52980(11) 0.85875(12) 0.33262(13) 0.0275(5) Uani 1 1 d . . . H22 H 0.5180(17) 0.8171(19) 0.3298(16) 0.030(8) Uiso 1 1 d . . . C31 C 0.25122(13) 0.50951(13) 0.16740(15) 0.0276(5) Uani 1 1 d . . . C32 C 0.18069(13) 0.45400(12) 0.16872(13) 0.0235(5) Uani 1 1 d . . . C33 C 0.12691(14) 0.47015(14) 0.16424(17) 0.0314(6) Uani 1 1 d . . . H33 H 0.0790(18) 0.4331(18) 0.1559(16) 0.035(8) Uiso 1 1 d . . . C34 C 0.14138(15) 0.53886(15) 0.15864(19) 0.0404(8) Uani 1 1 d . . . H34 H 0.104(2) 0.5483(19) 0.1569(18) 0.046(10) Uiso 1 1 d . . . C35 C 0.20995(17) 0.59244(16) 0.1595(2) 0.0468(9) Uani 1 1 d . . . H35 H 0.224(3) 0.637(3) 0.158(3) 0.084(15) Uiso 1 1 d . . . C36 C 0.26427(16) 0.57864(15) 0.1635(2) 0.0430(8) Uani 1 1 d . . . H36 H 0.3052(19) 0.6103(19) 0.1652(17) 0.038(9) Uiso 1 1 d . . . C37 C 0.16236(13) 0.37822(13) 0.17705(13) 0.0241(5) Uani 1 1 d . . . O31 O 0.20881(10) 0.36151(9) 0.17635(11) 0.0307(4) Uani 1 1 d . . . N31 N 0.09528(12) 0.32943(12) 0.18512(13) 0.0298(5) Uani 1 1 d . . . H31A H 0.0891(17) 0.2876(18) 0.1899(16) 0.030(8) Uiso 1 1 d . . . H31B H 0.0588(19) 0.3366(17) 0.1871(16) 0.033(9) Uiso 1 1 d . . . C38 C 0.37650(13) 0.53809(14) 0.16341(15) 0.0292(6) Uani 1 1 d . . . C39 C 0.41953(15) 0.50246(15) 0.16891(17) 0.0361(7) Uani 1 1 d . . . H39A H 0.4343 0.4966 0.1254 0.054 Uiso 1 1 calc R . . H39B H 0.3912 0.4561 0.1892 0.054 Uiso 1 1 calc R . . H39C H 0.4613 0.5313 0.1956 0.054 Uiso 1 1 calc R . . O32 O 0.40365(10) 0.60092(10) 0.15249(13) 0.0436(6) Uani 1 1 d . . . N32 N 0.30590(11) 0.49395(12) 0.17122(13) 0.0308(5) Uani 1 1 d . . . H32 H 0.2910(16) 0.4487(17) 0.1763(15) 0.023(7) Uiso 1 1 d . . . C41 C 0.51339(13) 0.88498(13) 0.16110(14) 0.0248(5) Uani 1 1 d . . . C42 C 0.50074(13) 0.81514(13) 0.16211(14) 0.0245(5) Uani 1 1 d . . . C43 C 0.43326(15) 0.76136(14) 0.14618(19) 0.0394(7) Uani 1 1 d . . . H43 H 0.429(2) 0.717(2) 0.151(2) 0.050(10) Uiso 1 1 d . . . C44 C 0.37924(16) 0.77350(16) 0.13125(19) 0.0415(8) Uani 1 1 d . . . H44 H 0.3321(19) 0.7340(19) 0.1142(17) 0.042(9) Uiso 1 1 d . . . C45 C 0.39214(15) 0.84166(16) 0.13196(19) 0.0401(7) Uani 1 1 d . . . H45 H 0.3540(17) 0.8495(17) 0.1209(16) 0.032(8) Uiso 1 1 d . . . C46 C 0.45800(15) 0.89709(15) 0.14671(17) 0.0355(7) Uani 1 1 d . . . H46 H 0.465(3) 0.943(3) 0.145(2) 0.081(15) Uiso 1 1 d . . . C47 C 0.55725(13) 0.79823(14) 0.17723(14) 0.0268(5) Uani 1 1 d . . . O41 O 0.61811(10) 0.84491(10) 0.19211(11) 0.0319(4) Uani 1 1 d . . . N41 N 0.54148(14) 0.73134(13) 0.17498(17) 0.0397(7) Uani 1 1 d . . . H41A H 0.571(2) 0.721(2) 0.1818(19) 0.045(10) Uiso 1 1 d . . . H41B H 0.501(2) 0.697(2) 0.1716(18) 0.040(9) Uiso 1 1 d . . . C48 C 0.60726(14) 1.01026(14) 0.16862(17) 0.0336(6) Uani 1 1 d . . . C49 C 0.68452(15) 1.05506(16) 0.18381(18) 0.0395(7) Uani 1 1 d . . . H49A H 0.7118 1.0657 0.1435 0.059 Uiso 1 1 calc R . . H49B H 0.6988 1.0295 0.2136 0.059 Uiso 1 1 calc R . . H49C H 0.6932 1.0991 0.2043 0.059 Uiso 1 1 calc R . . O42 O 0.57294(11) 1.03715(11) 0.15075(15) 0.0514(7) Uani 1 1 d . . . N42 N 0.58150(12) 0.94025(11) 0.17427(13) 0.0280(5) Uani 1 1 d . . . H42 H 0.6128(18) 0.9305(18) 0.1863(17) 0.034(9) Uiso 1 1 d . . . C51 C 0.25027(13) 0.39877(13) 0.33052(13) 0.0235(5) Uani 1 1 d . . . C52 C 0.32032(13) 0.45427(13) 0.33462(13) 0.0230(5) Uani 1 1 d . . . C53 C 0.37377(14) 0.43802(14) 0.33909(15) 0.0303(6) Uani 1 1 d . . . H53 H 0.4207(14) 0.4740(13) 0.3442(12) 0.009(6) Uiso 1 1 d . . . C54 C 0.35976(15) 0.36897(15) 0.33685(17) 0.0339(6) Uani 1 1 d . . . H54 H 0.3993(18) 0.3600(18) 0.3404(18) 0.041(9) Uiso 1 1 d . . . C55 C 0.29146(15) 0.31507(14) 0.32899(17) 0.0340(6) Uani 1 1 d . . . H55 H 0.2803(19) 0.261(2) 0.3273(19) 0.050(10) Uiso 1 1 d . . . C56 C 0.23658(14) 0.32913(14) 0.32640(15) 0.0292(6) Uani 1 1 d . . . H56 H 0.1884(18) 0.2912(18) 0.3240(17) 0.037(9) Uiso 1 1 d . . . C57 C 0.33821(13) 0.53022(13) 0.33256(14) 0.0251(5) Uani 1 1 d . . . O51 O 0.29099(9) 0.54618(9) 0.33539(12) 0.0365(5) Uani 1 1 d . . . N51 N 0.40501(12) 0.57999(13) 0.32586(14) 0.0322(5) Uani 1 1 d . . . H51A H 0.4145(19) 0.624(2) 0.3238(18) 0.044(10) Uiso 1 1 d . . . H51B H 0.439(2) 0.5746(19) 0.3198(18) 0.042(10) Uiso 1 1 d . . . C58 C 0.12587(13) 0.36968(14) 0.34090(15) 0.0281(6) Uani 1 1 d . . . C59 C 0.08004(14) 0.40240(15) 0.33465(17) 0.0345(6) Uani 1 1 d . . . H59A H 0.0420 0.3752 0.3035 0.052 Uiso 1 1 calc R . . H59B H 0.1085 0.4510 0.3192 0.052 Uiso 1 1 calc R . . H59C H 0.0597 0.4023 0.3771 0.052 Uiso 1 1 calc R . . O52 O 0.10148(11) 0.30872(11) 0.35791(14) 0.0468(6) Uani 1 1 d . . . N52 N 0.19502(11) 0.41355(11) 0.32775(12) 0.0252(5) Uani 1 1 d . . . H52 H 0.2056(14) 0.4545(15) 0.3238(13) 0.012(6) Uiso 1 1 d . . . C1S C 0.2098(2) 0.34744(19) 0.4943(2) 0.0557(10) Uani 1 1 d . . . H1SA H 0.1991 0.3342 0.4474 0.067 Uiso 1 1 calc R . . Cl1S Cl 0.21179(10) 0.42714(7) 0.50339(9) 0.0995(5) Uani 1 1 d . . . Cl2S Cl 0.14513(6) 0.28116(7) 0.53720(8) 0.0899(4) Uani 1 1 d . . . Cl3S Cl 0.29197(7) 0.35750(10) 0.50889(7) 0.0945(5) 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 C1 0.0197(11) 0.0186(11) 0.0259(12) -0.0031(9) -0.0040(9) 0.0095(9) C2 0.0197(11) 0.0174(11) 0.0303(13) -0.0021(9) -0.0022(10) 0.0100(10) C3 0.0188(12) 0.0217(12) 0.0484(17) -0.0013(11) -0.0011(11) 0.0090(11) C4 0.0259(14) 0.0287(14) 0.0544(18) 0.0035(13) -0.0004(13) 0.0176(12) C5 0.0296(14) 0.0187(12) 0.0461(17) 0.0040(11) -0.0003(12) 0.0138(11) C6 0.0209(12) 0.0165(12) 0.0391(15) 0.0007(10) -0.0007(11) 0.0057(10) C7 0.0190(12) 0.0141(11) 0.0390(15) -0.0028(10) -0.0025(10) 0.0059(9) O1 0.0191(9) 0.0183(9) 0.0645(14) 0.0029(9) 0.0023(9) 0.0102(7) N1 0.0197(11) 0.0158(11) 0.0632(17) 0.0045(10) 0.0062(11) 0.0089(9) C8 0.0201(12) 0.0216(12) 0.0365(15) -0.0003(10) -0.0009(10) 0.0097(10) C9 0.0205(12) 0.0307(14) 0.0557(19) 0.0016(13) -0.0015(12) 0.0143(11) O2 0.0188(9) 0.0192(9) 0.0682(15) 0.0001(9) -0.0018(9) 0.0044(8) N2 0.0194(10) 0.0165(10) 0.0407(13) 0.0015(9) -0.0002(9) 0.0077(9) C11 0.0220(12) 0.0207(12) 0.0312(13) -0.0001(10) 0.0035(10) 0.0090(10) C12 0.0198(12) 0.0197(12) 0.0320(13) -0.0003(10) 0.0019(10) 0.0090(10) C13 0.0225(13) 0.0224(13) 0.0436(16) 0.0000(11) -0.0017(12) 0.0092(11) C14 0.0363(16) 0.0302(15) 0.0501(18) 0.0006(13) -0.0049(13) 0.0221(13) C15 0.0386(16) 0.0202(13) 0.0483(18) 0.0033(12) 0.0000(13) 0.0134(12) C16 0.0271(14) 0.0196(13) 0.0422(16) -0.0006(11) -0.0019(12) 0.0066(11) C17 0.0194(11) 0.0177(11) 0.0371(14) -0.0007(10) 0.0021(10) 0.0085(10) O11 0.0199(9) 0.0180(9) 0.0745(15) -0.0011(9) -0.0057(9) 0.0082(7) N11 0.0175(11) 0.0179(11) 0.0496(15) 0.0011(10) 0.0010(10) 0.0081(9) C18 0.0217(12) 0.0258(13) 0.0448(16) -0.0030(12) 0.0014(12) 0.0098(11) C19 0.0257(14) 0.0352(16) 0.070(2) -0.0044(15) -0.0056(14) 0.0170(13) O12 0.0270(11) 0.0236(10) 0.095(2) -0.0155(12) -0.0108(12) 0.0072(9) N12 0.0182(10) 0.0183(11) 0.0470(14) -0.0019(10) -0.0004(9) 0.0062(9) C21 0.0227(12) 0.0176(11) 0.0389(14) 0.0014(10) 0.0007(11) 0.0121(10) C22 0.0201(11) 0.0154(11) 0.0393(15) 0.0029(10) 0.0040(10) 0.0093(9) C23 0.0179(12) 0.0192(12) 0.062(2) 0.0030(12) 0.0035(12) 0.0081(10) C24 0.0218(13) 0.0269(14) 0.069(2) 0.0063(14) 0.0045(13) 0.0158(12) C25 0.0318(15) 0.0164(12) 0.068(2) 0.0003(13) -0.0006(14) 0.0148(11) C26 0.0218(13) 0.0170(12) 0.0574(19) -0.0045(12) -0.0054(12) 0.0072(10) C27 0.0201(12) 0.0192(12) 0.0448(16) 0.0035(11) 0.0046(11) 0.0094(10) O21 0.0225(9) 0.0155(8) 0.0751(16) 0.0023(9) 0.0026(9) 0.0102(7) N21 0.0180(11) 0.0131(11) 0.079(2) 0.0031(11) 0.0079(12) 0.0058(9) C28 0.0259(13) 0.0226(13) 0.0431(16) -0.0008(11) -0.0048(12) 0.0112(11) C29 0.0279(14) 0.0357(15) 0.0542(19) -0.0006(14) -0.0062(13) 0.0200(13) O22 0.0257(10) 0.0196(10) 0.098(2) -0.0054(11) -0.0143(11) 0.0093(8) N22 0.0177(10) 0.0154(10) 0.0494(14) 0.0022(10) -0.0003(10) 0.0082(8) C31 0.0215(12) 0.0200(12) 0.0436(15) 0.0036(11) 0.0027(11) 0.0120(10) C32 0.0220(12) 0.0140(11) 0.0342(14) 0.0006(10) -0.0003(10) 0.0087(9) C33 0.0197(12) 0.0220(12) 0.0519(17) 0.0049(12) 0.0030(12) 0.0098(11) C34 0.0247(14) 0.0247(13) 0.078(2) 0.0056(15) 0.0038(14) 0.0173(12) C35 0.0347(16) 0.0182(13) 0.089(3) 0.0072(16) 0.0091(17) 0.0143(12) C36 0.0211(14) 0.0168(13) 0.087(3) 0.0052(15) 0.0066(15) 0.0061(11) C37 0.0226(12) 0.0155(11) 0.0338(14) -0.0018(10) -0.0012(10) 0.0093(9) O31 0.0219(9) 0.0167(8) 0.0545(12) 0.0012(8) 0.0029(9) 0.0104(7) N31 0.0210(11) 0.0133(10) 0.0548(15) 0.0004(10) -0.0026(10) 0.0084(9) C38 0.0209(12) 0.0210(12) 0.0450(16) -0.0015(11) -0.0001(11) 0.0099(10) C39 0.0246(13) 0.0273(14) 0.0577(19) 0.0006(13) 0.0027(13) 0.0140(11) O32 0.0207(10) 0.0185(9) 0.0850(18) 0.0055(10) 0.0032(10) 0.0049(8) N32 0.0193(10) 0.0154(10) 0.0564(16) 0.0027(10) 0.0019(10) 0.0077(9) C41 0.0187(11) 0.0171(11) 0.0372(14) -0.0002(10) -0.0008(10) 0.0079(9) C42 0.0204(12) 0.0163(11) 0.0371(14) -0.0008(10) -0.0012(10) 0.0094(10) C43 0.0266(14) 0.0144(12) 0.075(2) -0.0008(13) -0.0074(14) 0.0083(11) C44 0.0230(14) 0.0253(14) 0.073(2) 0.0001(14) -0.0119(14) 0.0094(12) C45 0.0228(14) 0.0264(14) 0.074(2) 0.0024(14) -0.0088(14) 0.0145(12) C46 0.0267(14) 0.0214(13) 0.061(2) 0.0013(13) -0.0052(13) 0.0141(11) C47 0.0217(12) 0.0227(12) 0.0373(14) -0.0016(11) 0.0029(11) 0.0122(10) O41 0.0198(9) 0.0221(9) 0.0566(13) -0.0053(9) -0.0048(8) 0.0125(8) N41 0.0188(11) 0.0204(11) 0.083(2) 0.0009(12) -0.0028(12) 0.0123(10) C48 0.0236(13) 0.0226(13) 0.0549(18) -0.0049(12) -0.0005(12) 0.0118(11) C49 0.0256(14) 0.0253(14) 0.059(2) -0.0075(13) -0.0035(13) 0.0065(11) O42 0.0290(11) 0.0199(10) 0.106(2) 0.0046(11) -0.0037(12) 0.0131(9) N42 0.0215(10) 0.0177(10) 0.0470(14) -0.0033(9) -0.0048(10) 0.0115(9) C51 0.0206(11) 0.0183(11) 0.0317(13) -0.0010(10) 0.0001(10) 0.0099(10) C52 0.0215(11) 0.0187(11) 0.0311(13) -0.0005(10) 0.0001(10) 0.0118(10) C53 0.0210(12) 0.0230(13) 0.0472(17) 0.0031(12) 0.0024(11) 0.0112(11) C54 0.0303(14) 0.0266(13) 0.0542(19) 0.0041(12) 0.0038(13) 0.0213(12) C55 0.0344(14) 0.0198(12) 0.0532(18) -0.0004(12) 0.0032(13) 0.0176(11) C56 0.0237(13) 0.0183(12) 0.0446(16) -0.0026(11) -0.0015(12) 0.0096(10) C57 0.0194(11) 0.0183(11) 0.0384(14) -0.0026(10) -0.0016(10) 0.0101(9) O51 0.0189(9) 0.0170(9) 0.0759(16) 0.0006(9) 0.0040(10) 0.0106(7) N51 0.0196(11) 0.0174(11) 0.0595(16) -0.0012(10) -0.0002(11) 0.0092(9) C58 0.0191(11) 0.0216(12) 0.0415(15) -0.0016(11) -0.0018(11) 0.0085(10) C59 0.0219(12) 0.0314(14) 0.0517(18) -0.0023(13) 0.0008(12) 0.0145(11) O52 0.0236(10) 0.0225(10) 0.0904(18) 0.0154(11) 0.0094(11) 0.0085(8) N52 0.0198(10) 0.0146(10) 0.0414(13) -0.0007(9) -0.0012(9) 0.0087(8) C1S 0.046(2) 0.046(2) 0.079(3) 0.0081(19) 0.0050(19) 0.0252(17) Cl1S 0.1445(13) 0.0615(7) 0.1166(12) -0.0234(7) -0.0259(10) 0.0696(9) Cl2S 0.0481(6) 0.0792(8) 0.1000(10) 0.0201(7) -0.0084(6) 0.0000(6) Cl3S 0.0570(7) 0.1616(14) 0.0889(9) 0.0036(9) 0.0071(6) 0.0727(9) _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 C6 1.395(3) . ? C1 C2 1.406(3) . ? C1 N2 1.411(3) . ? C2 C3 1.393(4) . ? C2 C7 1.501(3) . ? C3 C4 1.375(4) . ? C3 H3 0.90(3) . ? C4 C5 1.379(4) . ? C4 H4 0.93(4) . ? C5 C6 1.376(4) . ? C5 H5 0.98(3) . ? C6 H6 0.93(3) . ? C7 O1 1.249(3) . ? C7 N1 1.324(3) . ? N1 H1A 0.87(3) . ? N1 H1B 0.80(4) . ? C8 O2 1.216(3) . ? C8 N2 1.354(3) . ? C8 C9 1.505(4) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? N2 H2 0.81(3) . ? C11 C16 1.396(4) . ? C11 N12 1.398(3) . ? C11 C12 1.413(4) . ? C12 C13 1.395(4) . ? C12 C17 1.495(3) . ? C13 C14 1.380(4) . ? C13 H13 0.88(4) . ? C14 C15 1.378(4) . ? C14 H14 0.98(4) . ? C15 C16 1.364(4) . ? C15 H15 0.87(5) . ? C16 H16 0.90(4) . ? C17 O11 1.240(3) . ? C17 N11 1.329(3) . ? N11 H11A 0.76(5) . ? N11 H11B 0.78(3) . ? C18 O12 1.214(3) . ? C18 N12 1.350(4) . ? C18 C19 1.505(4) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? N12 H12 0.82(4) . ? C21 C26 1.396(3) . ? C21 N22 1.406(3) . ? C21 C22 1.415(3) . ? C22 C23 1.388(4) . ? C22 C27 1.502(3) . ? C23 C24 1.373(4) . ? C23 H23 0.98(3) . ? C24 C25 1.376(4) . ? C24 H24 0.93(4) . ? C25 C26 1.385(4) . ? C25 H25 0.90(4) . ? C26 H26 0.93(4) . ? C27 O21 1.241(3) . ? C27 N21 1.322(3) . ? N21 H21A 0.77(4) . ? N21 H21B 0.88(4) . ? C28 O22 1.223(3) . ? C28 N22 1.351(3) . ? C28 C29 1.506(4) . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? N22 H22 0.82(3) . ? C31 C36 1.396(4) . ? C31 N32 1.402(3) . ? C31 C32 1.410(3) . ? C32 C33 1.393(4) . ? C32 C37 1.510(3) . ? C33 C34 1.380(4) . ? C33 H33 0.97(3) . ? C34 C35 1.368(4) . ? C34 H34 0.95(4) . ? C35 C36 1.369(4) . ? C35 H35 0.86(5) . ? C36 H36 0.82(4) . ? C37 O31 1.242(3) . ? C37 N31 1.326(3) . ? N31 H31A 0.86(3) . ? N31 H31B 0.89(4) . ? C38 O32 1.217(3) . ? C38 N32 1.363(3) . ? C38 C39 1.499(4) . ? C39 H39A 0.9800 . ? C39 H39B 0.9800 . ? C39 H39C 0.9800 . ? N32 H32 0.88(3) . ? C41 C46 1.397(4) . ? C41 N42 1.400(3) . ? C41 C42 1.412(3) . ? C42 C43 1.393(4) . ? C42 C47 1.492(3) . ? C43 C44 1.371(4) . ? C43 H43 0.94(4) . ? C44 C45 1.374(4) . ? C44 H44 1.02(4) . ? C45 C46 1.377(4) . ? C45 H45 0.96(3) . ? C46 H46 0.94(5) . ? C47 O41 1.246(3) . ? C47 N41 1.328(3) . ? N41 H41A 0.79(4) . ? N41 H41B 0.83(4) . ? C48 O42 1.221(4) . ? C48 N42 1.349(3) . ? C48 C49 1.505(4) . ? C49 H49A 0.9800 . ? C49 H49B 0.9800 . ? C49 H49C 0.9800 . ? N42 H42 0.85(4) . ? C51 N52 1.402(3) . ? C51 C56 1.403(3) . ? C51 C52 1.405(3) . ? C52 C53 1.387(3) . ? C52 C57 1.507(3) . ? C53 C54 1.386(4) . ? C53 H53 0.94(3) . ? C54 C55 1.376(4) . ? C54 H54 0.98(4) . ? C55 C56 1.384(4) . ? C55 H55 1.08(4) . ? C56 H56 0.96(3) . ? C57 O51 1.248(3) . ? C57 N51 1.324(3) . ? N51 H51A 0.87(4) . ? N51 H51B 0.81(4) . ? C58 O52 1.216(3) . ? C58 N52 1.355(3) . ? C58 C59 1.503(4) . ? C59 H59A 0.9800 . ? C59 H59B 0.9800 . ? C59 H59C 0.9800 . ? N52 H52 0.81(3) . ? C1S Cl2S 1.684(4) . ? C1S Cl3S 1.728(4) . ? C1S Cl1S 1.735(4) . ? C1S H1SA 1.0000 . ? 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 C1 C2 119.6(2) . . ? C6 C1 N2 121.3(2) . . ? C2 C1 N2 119.0(2) . . ? C3 C2 C1 118.4(2) . . ? C3 C2 C7 119.4(2) . . ? C1 C2 C7 122.3(2) . . ? C4 C3 C2 121.5(3) . . ? C4 C3 H3 119(2) . . ? C2 C3 H3 119(2) . . ? C3 C4 C5 119.6(3) . . ? C3 C4 H4 115(2) . . ? C5 C4 H4 125(2) . . ? C6 C5 C4 120.6(2) . . ? C6 C5 H5 120.2(17) . . ? C4 C5 H5 119.2(17) . . ? C5 C6 C1 120.3(2) . . ? C5 C6 H6 118.6(18) . . ? C1 C6 H6 121.1(18) . . ? O1 C7 N1 120.1(2) . . ? O1 C7 C2 121.3(2) . . ? N1 C7 C2 118.6(2) . . ? C7 N1 H1A 119(2) . . ? C7 N1 H1B 121(2) . . ? H1A N1 H1B 120(3) . . ? O2 C8 N2 124.7(2) . . ? O2 C8 C9 121.5(2) . . ? N2 C8 C9 113.9(2) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 N2 C1 129.4(2) . . ? C8 N2 H2 116(2) . . ? C1 N2 H2 114(2) . . ? C16 C11 N12 121.6(2) . . ? C16 C11 C12 119.1(2) . . ? N12 C11 C12 119.3(2) . . ? C13 C12 C11 118.1(2) . . ? C13 C12 C17 120.3(2) . . ? C11 C12 C17 121.6(2) . . ? C14 C13 C12 121.9(3) . . ? C14 C13 H13 115(2) . . ? C12 C13 H13 123(2) . . ? C15 C14 C13 119.0(3) . . ? C15 C14 H14 124(2) . . ? C13 C14 H14 116(2) . . ? C16 C15 C14 120.9(3) . . ? C16 C15 H15 114(3) . . ? C14 C15 H15 125(3) . . ? C15 C16 C11 121.0(3) . . ? C15 C16 H16 117(2) . . ? C11 C16 H16 121(2) . . ? O11 C17 N11 119.6(2) . . ? O11 C17 C12 121.3(2) . . ? N11 C17 C12 119.0(2) . . ? C17 N11 H11A 117(3) . . ? C17 N11 H11B 124(2) . . ? H11A N11 H11B 117(4) . . ? O12 C18 N12 124.2(3) . . ? O12 C18 C19 121.5(3) . . ? N12 C18 C19 114.3(2) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C18 N12 C11 129.9(2) . . ? C18 N12 H12 119(3) . . ? C11 N12 H12 109(3) . . ? C26 C21 N22 121.7(2) . . ? C26 C21 C22 119.3(2) . . ? N22 C21 C22 119.0(2) . . ? C23 C22 C21 118.0(2) . . ? C23 C22 C27 120.4(2) . . ? C21 C22 C27 121.7(2) . . ? C24 C23 C22 122.5(3) . . ? C24 C23 H23 118.9(19) . . ? C22 C23 H23 118.2(19) . . ? C23 C24 C25 119.2(3) . . ? C23 C24 H24 118(2) . . ? C25 C24 H24 123(2) . . ? C24 C25 C26 120.6(3) . . ? C24 C25 H25 118(2) . . ? C26 C25 H25 121(2) . . ? C25 C26 C21 120.4(2) . . ? C25 C26 H26 124(2) . . ? C21 C26 H26 115(2) . . ? O21 C27 N21 120.8(2) . . ? O21 C27 C22 121.5(2) . . ? N21 C27 C22 117.7(2) . . ? C27 N21 H21A 115(3) . . ? C27 N21 H21B 129(2) . . ? H21A N21 H21B 116(4) . . ? O22 C28 N22 123.7(3) . . ? O22 C28 C29 121.4(3) . . ? N22 C28 C29 114.9(2) . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C28 N22 C21 129.9(2) . . ? C28 N22 H22 116(2) . . ? C21 N22 H22 114(2) . . ? C36 C31 N32 122.0(2) . . ? C36 C31 C32 118.6(2) . . ? N32 C31 C32 119.4(2) . . ? C33 C32 C31 118.8(2) . . ? C33 C32 C37 119.5(2) . . ? C31 C32 C37 121.7(2) . . ? C34 C33 C32 121.4(2) . . ? C34 C33 H33 117(2) . . ? C32 C33 H33 120(2) . . ? C35 C34 C33 119.3(3) . . ? C35 C34 H34 121(2) . . ? C33 C34 H34 119(2) . . ? C34 C35 C36 120.9(3) . . ? C34 C35 H35 126(3) . . ? C36 C35 H35 113(3) . . ? C35 C36 C31 120.9(3) . . ? C35 C36 H36 121(2) . . ? C31 C36 H36 118(2) . . ? O31 C37 N31 120.3(2) . . ? O31 C37 C32 121.1(2) . . ? N31 C37 C32 118.6(2) . . ? C37 N31 H31A 113(2) . . ? C37 N31 H31B 127(2) . . ? H31A N31 H31B 120(3) . . ? O32 C38 N32 124.3(2) . . ? O32 C38 C39 121.6(2) . . ? N32 C38 C39 114.1(2) . . ? C38 C39 H39A 109.5 . . ? C38 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? C38 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? C38 N32 C31 128.7(2) . . ? C38 N32 H32 117.5(19) . . ? C31 N32 H32 113.6(19) . . ? C46 C41 N42 121.9(2) . . ? C46 C41 C42 119.3(2) . . ? N42 C41 C42 118.8(2) . . ? C43 C42 C41 117.6(2) . . ? C43 C42 C47 120.0(2) . . ? C41 C42 C47 122.3(2) . . ? C44 C43 C42 122.9(3) . . ? C44 C43 H43 126(2) . . ? C42 C43 H43 111(2) . . ? C43 C44 C45 118.7(3) . . ? C43 C44 H44 121(2) . . ? C45 C44 H44 120(2) . . ? C44 C45 C46 121.1(3) . . ? C44 C45 H45 117.9(19) . . ? C46 C45 H45 121.0(19) . . ? C45 C46 C41 120.4(3) . . ? C45 C46 H46 118(3) . . ? C41 C46 H46 122(3) . . ? O41 C47 N41 119.7(2) . . ? O41 C47 C42 121.8(2) . . ? N41 C47 C42 118.5(2) . . ? C47 N41 H41A 120(3) . . ? C47 N41 H41B 125(2) . . ? H41A N41 H41B 114(4) . . ? O42 C48 N42 124.5(3) . . ? O42 C48 C49 120.7(3) . . ? N42 C48 C49 114.7(2) . . ? C48 C49 H49A 109.5 . . ? C48 C49 H49B 109.5 . . ? H49A C49 H49B 109.5 . . ? C48 C49 H49C 109.5 . . ? H49A C49 H49C 109.5 . . ? H49B C49 H49C 109.5 . . ? C48 N42 C41 128.8(2) . . ? C48 N42 H42 112(2) . . ? C41 N42 H42 119(2) . . ? N52 C51 C56 120.6(2) . . ? N52 C51 C52 119.9(2) . . ? C56 C51 C52 119.5(2) . . ? C53 C52 C51 118.6(2) . . ? C53 C52 C57 119.9(2) . . ? C51 C52 C57 121.5(2) . . ? C54 C53 C52 121.6(2) . . ? C54 C53 H53 118.2(15) . . ? C52 C53 H53 120.3(15) . . ? C55 C54 C53 119.5(2) . . ? C55 C54 H54 122(2) . . ? C53 C54 H54 119(2) . . ? C54 C55 C56 120.5(2) . . ? C54 C55 H55 120(2) . . ? C56 C55 H55 120(2) . . ? C55 C56 C51 120.2(2) . . ? C55 C56 H56 121(2) . . ? C51 C56 H56 119(2) . . ? O51 C57 N51 120.2(2) . . ? O51 C57 C52 120.9(2) . . ? N51 C57 C52 118.8(2) . . ? C57 N51 H51A 118(2) . . ? C57 N51 H51B 127(3) . . ? H51A N51 H51B 115(3) . . ? O52 C58 N52 123.9(2) . . ? O52 C58 C59 121.1(2) . . ? N52 C58 C59 114.9(2) . . ? C58 C59 H59A 109.5 . . ? C58 C59 H59B 109.5 . . ? H59A C59 H59B 109.5 . . ? C58 C59 H59C 109.5 . . ? H59A C59 H59C 109.5 . . ? H59B C59 H59C 109.5 . . ? C58 N52 C51 128.1(2) . . ? C58 N52 H52 113.9(19) . . ? C51 N52 H52 117.2(19) . . ? Cl2S C1S Cl3S 113.1(2) . . ? Cl2S C1S Cl1S 113.5(2) . . ? Cl3S C1S Cl1S 110.6(2) . . ? Cl2S C1S H1SA 106.3 . . ? Cl3S C1S H1SA 106.3 . . ? Cl1S C1S H1SA 106.3 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.3(4) . . . . ? N2 C1 C2 C3 179.4(2) . . . . ? C6 C1 C2 C7 179.6(2) . . . . ? N2 C1 C2 C7 -0.6(4) . . . . ? C1 C2 C3 C4 -0.2(4) . . . . ? C7 C2 C3 C4 179.9(3) . . . . ? C2 C3 C4 C5 1.2(5) . . . . ? C3 C4 C5 C6 -1.7(5) . . . . ? C4 C5 C6 C1 1.2(5) . . . . ? C2 C1 C6 C5 -0.2(4) . . . . ? N2 C1 C6 C5 -179.9(3) . . . . ? C3 C2 C7 O1 -168.6(3) . . . . ? C1 C2 C7 O1 11.4(4) . . . . ? C3 C2 C7 N1 11.8(4) . . . . ? C1 C2 C7 N1 -168.2(3) . . . . ? O2 C8 N2 C1 2.2(5) . . . . ? C9 C8 N2 C1 -177.8(3) . . . . ? C6 C1 N2 C8 -9.9(4) . . . . ? C2 C1 N2 C8 170.4(3) . . . . ? C16 C11 C12 C13 2.0(4) . . . . ? N12 C11 C12 C13 -178.8(3) . . . . ? C16 C11 C12 C17 -177.5(3) . . . . ? N12 C11 C12 C17 1.7(4) . . . . ? C11 C12 C13 C14 -0.5(4) . . . . ? C17 C12 C13 C14 179.0(3) . . . . ? C12 C13 C14 C15 -0.8(5) . . . . ? C13 C14 C15 C16 0.6(5) . . . . ? C14 C15 C16 C11 0.9(5) . . . . ? N12 C11 C16 C15 178.6(3) . . . . ? C12 C11 C16 C15 -2.2(5) . . . . ? C13 C12 C17 O11 -179.8(3) . . . . ? C11 C12 C17 O11 -0.4(4) . . . . ? C13 C12 C17 N11 -0.9(4) . . . . ? C11 C12 C17 N11 178.6(3) . . . . ? O12 C18 N12 C11 5.7(5) . . . . ? C19 C18 N12 C11 -174.2(3) . . . . ? C16 C11 N12 C18 -12.4(5) . . . . ? C12 C11 N12 C18 168.4(3) . . . . ? C26 C21 C22 C23 1.1(4) . . . . ? N22 C21 C22 C23 -178.7(3) . . . . ? C26 C21 C22 C27 -179.9(3) . . . . ? N22 C21 C22 C27 0.2(4) . . . . ? C21 C22 C23 C24 -1.6(5) . . . . ? C27 C22 C23 C24 179.5(3) . . . . ? C22 C23 C24 C25 1.3(5) . . . . ? C23 C24 C25 C26 -0.5(6) . . . . ? C24 C25 C26 C21 0.1(5) . . . . ? N22 C21 C26 C25 179.4(3) . . . . ? C22 C21 C26 C25 -0.4(5) . . . . ? C23 C22 C27 O21 170.8(3) . . . . ? C21 C22 C27 O21 -8.1(5) . . . . ? C23 C22 C27 N21 -9.8(4) . . . . ? C21 C22 C27 N21 171.3(3) . . . . ? O22 C28 N22 C21 3.3(5) . . . . ? C29 C28 N22 C21 -177.1(3) . . . . ? C26 C21 N22 C28 5.3(5) . . . . ? C22 C21 N22 C28 -174.9(3) . . . . ? C36 C31 C32 C33 1.8(5) . . . . ? N32 C31 C32 C33 -179.4(3) . . . . ? C36 C31 C32 C37 -176.2(3) . . . . ? N32 C31 C32 C37 2.7(4) . . . . ? C31 C32 C33 C34 0.0(5) . . . . ? C37 C32 C33 C34 178.0(3) . . . . ? C32 C33 C34 C35 -2.0(6) . . . . ? C33 C34 C35 C36 2.3(6) . . . . ? C34 C35 C36 C31 -0.5(7) . . . . ? N32 C31 C36 C35 179.6(4) . . . . ? C32 C31 C36 C35 -1.5(6) . . . . ? C33 C32 C37 O31 174.6(3) . . . . ? C31 C32 C37 O31 -7.5(4) . . . . ? C33 C32 C37 N31 -5.3(4) . . . . ? C31 C32 C37 N31 172.6(3) . . . . ? O32 C38 N32 C31 1.4(5) . . . . ? C39 C38 N32 C31 -178.2(3) . . . . ? C36 C31 N32 C38 -9.4(5) . . . . ? C32 C31 N32 C38 171.8(3) . . . . ? C46 C41 C42 C43 2.3(4) . . . . ? N42 C41 C42 C43 -177.4(3) . . . . ? C46 C41 C42 C47 -179.8(3) . . . . ? N42 C41 C42 C47 0.5(4) . . . . ? C41 C42 C43 C44 -1.5(5) . . . . ? C47 C42 C43 C44 -179.4(3) . . . . ? C42 C43 C44 C45 0.0(6) . . . . ? C43 C44 C45 C46 0.6(6) . . . . ? C44 C45 C46 C41 0.2(6) . . . . ? N42 C41 C46 C45 177.9(3) . . . . ? C42 C41 C46 C45 -1.7(5) . . . . ? C43 C42 C47 O41 -179.5(3) . . . . ? C41 C42 C47 O41 2.7(4) . . . . ? C43 C42 C47 N41 0.1(4) . . . . ? C41 C42 C47 N41 -177.7(3) . . . . ? O42 C48 N42 C41 0.7(6) . . . . ? C49 C48 N42 C41 -177.1(3) . . . . ? C46 C41 N42 C48 -8.2(5) . . . . ? C42 C41 N42 C48 171.5(3) . . . . ? N52 C51 C52 C53 178.3(3) . . . . ? C56 C51 C52 C53 -4.5(4) . . . . ? N52 C51 C52 C57 -3.3(4) . . . . ? C56 C51 C52 C57 174.0(3) . . . . ? C51 C52 C53 C54 2.7(5) . . . . ? C57 C52 C53 C54 -175.8(3) . . . . ? C52 C53 C54 C55 1.1(5) . . . . ? C53 C54 C55 C56 -3.1(5) . . . . ? C54 C55 C56 C51 1.2(5) . . . . ? N52 C51 C56 C55 179.8(3) . . . . ? C52 C51 C56 C55 2.6(4) . . . . ? C53 C52 C57 O51 -172.5(3) . . . . ? C51 C52 C57 O51 9.1(4) . . . . ? C53 C52 C57 N51 9.4(4) . . . . ? C51 C52 C57 N51 -169.0(3) . . . . ? O52 C58 N52 C51 0.3(5) . . . . ? C59 C58 N52 C51 178.8(3) . . . . ? C56 C51 N52 C58 22.0(4) . . . . ? C52 C51 N52 C58 -160.8(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 O1 0.81(3) 1.94(4) 2.624(3) 142(3) . N12 H12 O11 0.82(4) 1.86(4) 2.590(3) 148(4) . N22 H22 O21 0.82(3) 1.91(3) 2.605(3) 142(3) . N32 H32 O31 0.88(3) 1.86(3) 2.605(3) 141(3) . N42 H42 O41 0.85(4) 1.94(3) 2.611(3) 135(3) . N52 H52 O51 0.81(3) 1.96(3) 2.604(3) 136(2) . N1 H1A O31 0.87(3) 2.07(3) 2.931(3) 173(3) . N1 H1B O52 0.80(4) 2.22(4) 2.987(3) 161(3) 5_554 C3 H3 O52 0.90(3) 2.44(4) 3.292(3) 160(3) 5_554 N11 H11A O41 0.76(5) 2.22(5) 2.985(3) 178(5) 5_564 N11 H11B O2 0.78(3) 2.18(3) 2.949(3) 168(3) 5_664 C13 H13 O2 0.88(4) 2.48(4) 3.332(3) 164(3) 5_664 N21 H21A O51 0.77(4) 2.16(4) 2.903(3) 163(4) . N21 H21B O12 0.88(4) 2.10(4) 2.982(3) 177(4) 2_665 C23 H23 O12 0.98(3) 2.35(3) 3.247(3) 152(3) 2_665 N31 H31A O1 0.86(3) 2.07(4) 2.929(3) 172(3) . N31 H31B O22 0.89(4) 2.09(4) 2.970(3) 174(3) 5_454 C33 H33 O22 0.97(3) 2.34(3) 3.242(3) 154(3) 5_454 N41 H41A O11 0.79(4) 2.12(4) 2.898(3) 172(4) 6_655 N41 H41B O32 0.83(4) 2.16(4) 2.978(3) 171(4) . C43 H43 O32 0.94(4) 2.31(4) 3.243(3) 171(3) . N51 H51A O21 0.87(4) 2.04(4) 2.912(3) 179(4) . N51 H51B O42 0.81(4) 2.15(4) 2.951(3) 170(4) 6_655 C53 H53 O42 0.94(3) 2.43(3) 3.323(4) 160(2) 6_655 C1S H1SA O52 1.00 2.66 3.493(5) 140.7 . C5 H5 Cl2S 0.98(3) 2.80(3) 3.438(3) 124(2) 3_554 C25 H25 Cl3S 0.90(4) 2.85(4) 3.590(3) 141(3) 5_564 C45 H45 Cl1S 0.96(3) 2.82(3) 3.529(3) 131(2) 3_564 _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.789 _refine_diff_density_min -0.685 _refine_diff_density_rms 0.063 data_[(AABA)6.(1-PrOH)] _database_code_depnum_ccdc_archive 'CCDC 294940' _audit_creation_method SHELXL-97 _chemical_name_systematic ; o-Acetamidobenzamide 1-propanol solvate (6/1) ; _chemical_name_common (C9H10N2O2)6.(C3H8O) _chemical_melting_point ? _chemical_formula_moiety 'C9.50 H11.33 N2 O2.17' _chemical_formula_sum 'C9.50 H11.33 N2 O2.17' _chemical_formula_weight 188.21 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' 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.6040(9) _cell_length_b 17.5606(16) _cell_length_c 18.3598(17) _cell_angle_alpha 72.468(2) _cell_angle_beta 86.767(2) _cell_angle_gamma 75.422(2) _cell_volume 2856.9(5) _cell_formula_units_Z 12 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2962 _cell_measurement_theta_min 2.192 _cell_measurement_theta_max 24.586 _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.313 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1196 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7918 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS v2.10' _exptl_special_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 SMART APEX diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% None _diffrn_reflns_number 25626 _diffrn_reflns_av_R_equivalents 0.0311 _diffrn_reflns_av_sigmaI/netI 0.0716 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.44 _diffrn_reflns_theta_max 28.31 _reflns_number_total 13233 _reflns_number_gt 7588 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _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^)+(0.0758P)^2^+0.4965P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary 'direct methods' _atom_sites_solution_secondary 'difference Fourier synthesis' _atom_sites_solution_hydrogens ; those on O1s, C1S and C2S geometrically placed; others found from delta F ; _refine_ls_hydrogen_treatment ; those on O1S, C1S and C2S riding; methyl H rigid rotor model; others freely refined ; _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 13229 _refine_ls_number_parameters 914 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1220 _refine_ls_R_factor_gt 0.0617 _refine_ls_wR_factor_ref 0.1688 _refine_ls_wR_factor_gt 0.1377 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.0225(3) 0.30260(14) 0.13497(13) 0.0277(5) Uani 1 1 d . . . C2 C 0.0144(3) 0.22925(14) 0.19273(14) 0.0288(5) Uani 1 1 d . . . C3 C -0.0589(3) 0.17771(17) 0.17496(15) 0.0372(6) Uani 1 1 d . . . H3 H -0.069(3) 0.1290(18) 0.2094(16) 0.054(9) Uiso 1 1 d . . . C4 C -0.1191(3) 0.19552(18) 0.10380(16) 0.0419(7) Uani 1 1 d . . . H4 H -0.162(3) 0.1569(16) 0.0933(15) 0.045(8) Uiso 1 1 d . . . C5 C -0.1091(3) 0.26645(17) 0.04809(16) 0.0386(6) Uani 1 1 d . . . H5 H -0.148(3) 0.2805(15) -0.0003(15) 0.040(7) Uiso 1 1 d . . . C6 C -0.0398(3) 0.32022(15) 0.06328(15) 0.0339(6) Uani 1 1 d . . . H6 H -0.041(2) 0.3701(13) 0.0237(13) 0.020(6) Uiso 1 1 d . . . C7 C 0.0876(3) 0.20497(14) 0.26910(13) 0.0281(5) Uani 1 1 d . . . O1 O 0.14132(19) 0.25345(10) 0.28899(9) 0.0345(4) Uani 1 1 d . . . N1 N 0.0974(3) 0.12931(14) 0.31558(13) 0.0346(5) Uani 1 1 d . . . H1A H 0.141(3) 0.1169(16) 0.3591(16) 0.039(8) Uiso 1 1 d . . . H1B H 0.067(3) 0.0949(17) 0.3058(16) 0.040(8) Uiso 1 1 d . . . C8 C 0.1505(3) 0.41435(14) 0.10166(15) 0.0330(6) Uani 1 1 d . . . C9 C 0.2203(3) 0.46180(15) 0.13771(15) 0.0385(6) Uani 1 1 d . . . H9A H 0.3115 0.4677 0.1126 0.058 Uiso 1 1 calc R . . H9B H 0.2389 0.4322 0.1921 0.058 Uiso 1 1 calc R . . H9C H 0.1564 0.5165 0.1320 0.058 Uiso 1 1 calc R . . O2 O 0.1470(2) 0.42724(13) 0.03316(10) 0.0537(6) Uani 1 1 d . . . N2 N 0.0922(2) 0.35694(12) 0.15162(12) 0.0293(5) Uani 1 1 d . . . H2 H 0.119(3) 0.3447(14) 0.2019(15) 0.031(7) Uiso 1 1 d . . . C11 C 0.0952(2) 0.49328(14) 0.74739(13) 0.0257(5) Uani 1 1 d . . . C12 C 0.1699(2) 0.47252(14) 0.81717(13) 0.0264(5) Uani 1 1 d . . . C13 C 0.1674(3) 0.39776(14) 0.87190(14) 0.0305(6) Uani 1 1 d . . . H13 H 0.214(3) 0.3845(14) 0.9196(14) 0.029(6) Uiso 1 1 d . . . C14 C 0.0943(3) 0.34487(15) 0.85925(15) 0.0330(6) Uani 1 1 d . . . H14 H 0.089(3) 0.2950(15) 0.8986(14) 0.035(7) Uiso 1 1 d . . . C15 C 0.0212(3) 0.36568(15) 0.79069(14) 0.0327(6) Uani 1 1 d . . . H15 H -0.032(2) 0.3312(14) 0.7814(13) 0.028(6) Uiso 1 1 d . . . C16 C 0.0212(3) 0.43915(15) 0.73483(15) 0.0323(6) Uani 1 1 d . . . H16 H -0.032(3) 0.4526(15) 0.6880(15) 0.036(7) Uiso 1 1 d . . . C17 C 0.2533(3) 0.52755(14) 0.83352(14) 0.0282(5) Uani 1 1 d . . . O11 O 0.29513(19) 0.58010(10) 0.78053(9) 0.0360(4) Uani 1 1 d . . . N11 N 0.2850(3) 0.51692(14) 0.90581(12) 0.0342(5) Uani 1 1 d . . . H11A H 0.246(3) 0.4879(17) 0.9447(16) 0.042(8) Uiso 1 1 d . . . H11B H 0.335(3) 0.556(2) 0.9143(18) 0.069(10) Uiso 1 1 d . . . C18 C 0.0215(3) 0.60691(14) 0.62568(13) 0.0293(5) Uani 1 1 d . . . C19 C 0.0561(3) 0.68615(14) 0.57933(14) 0.0337(6) Uani 1 1 d . . . H19A H 0.0615 0.6884 0.5253 0.050 Uiso 1 1 calc R . . H19B H 0.1488 0.6889 0.5968 0.050 Uiso 1 1 calc R . . H19C H -0.0194 0.7328 0.5857 0.050 Uiso 1 1 calc R . . O12 O -0.0709(2) 0.58063(11) 0.60452(10) 0.0407(5) Uani 1 1 d . . . N12 N 0.0991(2) 0.56820(12) 0.69182(11) 0.0289(5) Uani 1 1 d . . . H12 H 0.155(3) 0.5938(16) 0.7043(15) 0.038(8) Uiso 1 1 d . . . C21 C 0.6418(2) 0.41382(14) 0.49150(13) 0.0269(5) Uani 1 1 d . . . C22 C 0.7342(3) 0.46303(13) 0.49752(13) 0.0262(5) Uani 1 1 d . . . C23 C 0.8308(3) 0.43352(15) 0.55917(15) 0.0330(6) Uani 1 1 d . . . H23 H 0.894(3) 0.4623(14) 0.5609(13) 0.027(7) Uiso 1 1 d . . . C24 C 0.8331(3) 0.36097(16) 0.61560(15) 0.0389(7) Uani 1 1 d . . . H24 H 0.903(3) 0.3421(14) 0.6545(15) 0.034(7) Uiso 1 1 d . . . C25 C 0.7343(3) 0.31671(16) 0.61300(15) 0.0387(7) Uani 1 1 d . . . H25 H 0.730(3) 0.2675(18) 0.6559(17) 0.056(9) Uiso 1 1 d . . . C26 C 0.6396(3) 0.34268(15) 0.55145(14) 0.0339(6) Uani 1 1 d . . . H26 H 0.570(3) 0.3131(14) 0.5499(13) 0.029(6) Uiso 1 1 d . . . C27 C 0.7312(2) 0.54445(14) 0.43938(14) 0.0275(5) Uani 1 1 d . . . O21 O 0.66992(19) 0.56461(10) 0.37585(9) 0.0341(4) Uani 1 1 d . . . N21 N 0.7942(2) 0.59532(13) 0.45813(14) 0.0362(5) Uani 1 1 d . . . H21A H 0.832(3) 0.5870(16) 0.5057(16) 0.044(8) Uiso 1 1 d . . . H21B H 0.796(3) 0.6459(17) 0.4245(15) 0.041(8) Uiso 1 1 d . . . C28 C 0.4856(3) 0.39179(15) 0.40040(14) 0.0311(6) Uani 1 1 d . . . C29 C 0.4019(3) 0.43622(16) 0.32658(15) 0.0384(6) Uani 1 1 d . . . H29A H 0.4590 0.4225 0.2842 0.058 Uiso 1 1 calc R . . H29B H 0.3807 0.4958 0.3184 0.058 Uiso 1 1 calc R . . H29C H 0.3116 0.4193 0.3290 0.058 Uiso 1 1 calc R . . O22 O 0.4921(2) 0.31944(11) 0.43301(10) 0.0455(5) Uani 1 1 d . . . N22 N 0.5519(2) 0.43829(12) 0.42645(12) 0.0307(5) Uani 1 1 d . . . H22 H 0.557(3) 0.4897(15) 0.3907(14) 0.035(7) Uiso 1 1 d . . . C31 C 0.4307(3) 0.01845(14) 0.60077(13) 0.0287(5) Uani 1 1 d . . . C32 C 0.4115(3) 0.09917(14) 0.54988(13) 0.0282(5) Uani 1 1 d . . . C33 C 0.4803(3) 0.15181(16) 0.56930(15) 0.0353(6) Uani 1 1 d . . . H33 H 0.462(3) 0.2068(17) 0.5402(15) 0.044(8) Uiso 1 1 d . . . C34 C 0.5671(3) 0.12724(17) 0.63301(15) 0.0379(6) Uani 1 1 d . . . H34 H 0.610(3) 0.1664(16) 0.6458(14) 0.041(7) Uiso 1 1 d . . . C35 C 0.5893(3) 0.04737(17) 0.67987(16) 0.0393(6) Uani 1 1 d . . . H35 H 0.650(3) 0.0301(16) 0.7231(16) 0.048(8) Uiso 1 1 d . . . C36 C 0.5218(3) -0.00678(16) 0.66451(15) 0.0357(6) Uani 1 1 d . . . H36 H 0.538(3) -0.0638(16) 0.6972(14) 0.038(7) Uiso 1 1 d . . . C37 C 0.3222(3) 0.12848(14) 0.47838(14) 0.0295(5) Uani 1 1 d . . . O31 O 0.24521(19) 0.08674(10) 0.46424(10) 0.0378(4) Uani 1 1 d . . . N31 N 0.3267(3) 0.20032(14) 0.42813(14) 0.0379(6) Uani 1 1 d . . . H31A H 0.280(3) 0.2136(15) 0.3873(16) 0.037(8) Uiso 1 1 d . . . H31B H 0.381(3) 0.2312(17) 0.4348(16) 0.050(9) Uiso 1 1 d . . . C38 C 0.3430(3) -0.10987(14) 0.62916(14) 0.0331(6) Uani 1 1 d . . . C39 C 0.2541(3) -0.14823(16) 0.59360(16) 0.0425(7) Uani 1 1 d . . . H39A H 0.3160 -0.1963 0.5814 0.064 Uiso 1 1 calc R . . H39B H 0.2076 -0.1080 0.5466 0.064 Uiso 1 1 calc R . . H39C H 0.1805 -0.1656 0.6294 0.064 Uiso 1 1 calc R . . O32 O 0.3981(2) -0.14401(11) 0.69293(10) 0.0455(5) Uani 1 1 d . . . N32 N 0.3580(2) -0.03488(12) 0.58460(12) 0.0321(5) Uani 1 1 d . . . H32 H 0.302(3) -0.0151(17) 0.5427(17) 0.055(9) Uiso 1 1 d . . . C41 C 0.4527(2) 0.25327(14) 0.02052(13) 0.0281(5) Uani 1 1 d . . . C42 C 0.4636(2) 0.25507(14) 0.09601(13) 0.0275(5) Uani 1 1 d . . . C43 C 0.4022(3) 0.20191(15) 0.15353(15) 0.0308(6) Uani 1 1 d . . . H43 H 0.408(3) 0.2033(14) 0.2030(14) 0.030(7) Uiso 1 1 d . . . C44 C 0.3329(3) 0.14868(15) 0.13748(15) 0.0327(6) Uani 1 1 d . . . H44 H 0.290(3) 0.1139(15) 0.1774(14) 0.035(7) Uiso 1 1 d . . . C45 C 0.3208(3) 0.14888(15) 0.06343(16) 0.0355(6) Uani 1 1 d . . . H45 H 0.271(3) 0.1117(16) 0.0522(14) 0.042(7) Uiso 1 1 d . . . C46 C 0.3801(3) 0.20038(15) 0.00503(15) 0.0339(6) Uani 1 1 d . . . H46 H 0.372(3) 0.2010(15) -0.0449(14) 0.034(7) Uiso 1 1 d . . . C47 C 0.5323(3) 0.31459(14) 0.11487(14) 0.0294(5) Uani 1 1 d . . . O41 O 0.54439(19) 0.37924(10) 0.06495(9) 0.0340(4) Uani 1 1 d . . . N41 N 0.5782(2) 0.29763(14) 0.18620(12) 0.0348(5) Uani 1 1 d . . . H41A H 0.626(3) 0.3351(16) 0.1974(14) 0.039(7) Uiso 1 1 d . . . H41B H 0.583(3) 0.2453(18) 0.2252(16) 0.053(9) Uiso 1 1 d . . . C48 C 0.5445(3) 0.30539(15) -0.10986(14) 0.0316(6) Uani 1 1 d . . . C49 C 0.5984(3) 0.37655(17) -0.15986(16) 0.0481(7) Uani 1 1 d . . . H49A H 0.7002 0.3573 -0.1705 0.072 Uiso 1 1 calc R . . H49B H 0.5876 0.4187 -0.1337 0.072 Uiso 1 1 calc R . . H49C H 0.5427 0.4001 -0.2080 0.072 Uiso 1 1 calc R . . O42 O 0.53477(19) 0.24870(10) -0.13359(10) 0.0376(4) Uani 1 1 d . . . N42 N 0.5102(2) 0.30921(13) -0.03870(12) 0.0324(5) Uani 1 1 d . . . H42 H 0.520(3) 0.3524(18) -0.0240(17) 0.060(9) Uiso 1 1 d . . . C51 C 0.7808(3) 0.91561(14) 0.24691(14) 0.0282(5) Uani 1 1 d . . . C52 C 0.7126(3) 0.85926(14) 0.23209(14) 0.0278(5) Uani 1 1 d . . . C53 C 0.6268(3) 0.88550(15) 0.16608(15) 0.0357(6) Uani 1 1 d . . . H53 H 0.582(3) 0.8471(16) 0.1567(14) 0.041(7) Uiso 1 1 d . . . C54 C 0.6057(3) 0.96429(16) 0.11633(16) 0.0400(7) Uani 1 1 d . . . H54 H 0.545(3) 0.9798(15) 0.0679(15) 0.041(7) Uiso 1 1 d . . . C55 C 0.6693(3) 1.01961(16) 0.13308(16) 0.0384(6) Uani 1 1 d . . . H55 H 0.653(3) 1.0758(17) 0.0986(16) 0.053(8) Uiso 1 1 d . . . C56 C 0.7558(3) 0.99606(15) 0.19728(16) 0.0351(6) Uani 1 1 d . . . H56 H 0.791(3) 1.0360(16) 0.2099(15) 0.043(8) Uiso 1 1 d . . . C57 C 0.7275(3) 0.77410(14) 0.28542(14) 0.0297(5) Uani 1 1 d . . . O51 O 0.8115(2) 0.74655(10) 0.34198(10) 0.0396(5) Uani 1 1 d . . . N51 N 0.6474(3) 0.72777(14) 0.27227(14) 0.0361(5) Uani 1 1 d . . . H51A H 0.591(3) 0.7435(16) 0.2318(16) 0.040(8) Uiso 1 1 d . . . H51B H 0.657(3) 0.6726(18) 0.3018(17) 0.053(9) Uiso 1 1 d . . . C58 C 0.9506(3) 0.93122(15) 0.33675(14) 0.0319(6) Uani 1 1 d . . . C59 C 1.0314(3) 0.88357(16) 0.41075(15) 0.0387(6) Uani 1 1 d . . . H59A H 1.1234 0.8984 0.4100 0.058 Uiso 1 1 calc R . . H59B H 1.0493 0.8244 0.4173 0.058 Uiso 1 1 calc R . . H59C H 0.9743 0.8969 0.4532 0.058 Uiso 1 1 calc R . . O52 O 0.9577(2) 1.00160(11) 0.30351(11) 0.0484(5) Uani 1 1 d . . . N52 N 0.8699(2) 0.88999(13) 0.31247(12) 0.0321(5) Uani 1 1 d . . . H52 H 0.874(3) 0.8386(18) 0.3436(17) 0.054(9) Uiso 1 1 d . . . O1S O 0.7573(3) 0.16457(17) 0.78652(13) 0.0870(9) Uani 1 1 d . . . H1S H 0.6913 0.1926 0.8065 0.130 Uiso 1 1 calc R . . C1S C 0.8103(4) 0.0850(2) 0.8398(2) 0.0803(12) Uani 1 1 d . . . H1SA H 0.8960 0.0552 0.8182 0.096 Uiso 1 1 calc R . . H1SB H 0.7359 0.0536 0.8460 0.096 Uiso 1 1 calc R . . C2S C 0.8500(5) 0.0863(2) 0.9163(2) 0.0843(12) Uani 1 1 d . . . H2SA H 0.8854 0.0289 0.9492 0.101 Uiso 1 1 calc R . . H2SB H 0.7630 0.1122 0.9399 0.101 Uiso 1 1 calc R . . C3S C 0.9628(5) 0.1320(3) 0.9134(3) 0.0999(15) Uani 1 1 d . . . H3S1 H 1.0524 0.1034 0.8949 0.150 Uiso 1 1 calc R . . H3S2 H 0.9793 0.1346 0.9647 0.150 Uiso 1 1 calc R . . H3S3 H 0.9307 0.1880 0.8786 0.150 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 0.0290(13) 0.0260(12) 0.0275(13) -0.0060(10) 0.0001(10) -0.0076(10) C2 0.0299(13) 0.0289(12) 0.0286(13) -0.0077(10) -0.0001(10) -0.0101(10) C3 0.0429(16) 0.0347(14) 0.0344(15) -0.0014(12) -0.0039(12) -0.0200(12) C4 0.0489(17) 0.0425(16) 0.0418(17) -0.0090(13) -0.0084(13) -0.0266(14) C5 0.0428(16) 0.0437(16) 0.0304(15) -0.0072(12) -0.0103(13) -0.0149(13) C6 0.0395(15) 0.0293(13) 0.0289(14) -0.0016(11) -0.0032(12) -0.0091(11) C7 0.0299(13) 0.0268(12) 0.0281(13) -0.0070(10) 0.0042(10) -0.0099(10) O1 0.0506(11) 0.0297(9) 0.0259(9) -0.0031(7) -0.0047(8) -0.0197(8) N1 0.0470(14) 0.0298(12) 0.0286(13) -0.0030(10) -0.0086(11) -0.0174(11) C8 0.0381(15) 0.0260(12) 0.0325(15) -0.0032(11) -0.0020(12) -0.0096(11) C9 0.0458(16) 0.0299(13) 0.0414(16) -0.0079(12) -0.0034(13) -0.0148(12) O2 0.0804(16) 0.0651(13) 0.0270(11) -0.0051(9) 0.0002(10) -0.0483(12) N2 0.0419(13) 0.0241(10) 0.0221(11) -0.0033(8) -0.0034(9) -0.0119(9) C11 0.0286(12) 0.0264(12) 0.0233(12) -0.0075(10) 0.0038(10) -0.0095(10) C12 0.0276(13) 0.0252(12) 0.0280(13) -0.0079(10) 0.0001(10) -0.0091(10) C13 0.0369(14) 0.0282(12) 0.0257(13) -0.0048(10) -0.0046(11) -0.0095(11) C14 0.0428(15) 0.0257(12) 0.0302(14) -0.0029(11) -0.0009(12) -0.0143(11) C15 0.0423(15) 0.0294(13) 0.0337(14) -0.0112(11) -0.0001(12) -0.0193(12) C16 0.0419(15) 0.0316(13) 0.0270(14) -0.0083(11) -0.0046(12) -0.0147(11) C17 0.0298(13) 0.0250(12) 0.0314(14) -0.0067(10) -0.0036(11) -0.0106(10) O11 0.0475(11) 0.0403(10) 0.0257(9) -0.0046(8) -0.0041(8) -0.0258(9) N11 0.0474(14) 0.0351(12) 0.0249(12) -0.0047(10) -0.0040(10) -0.0230(11) C18 0.0381(14) 0.0284(12) 0.0237(13) -0.0088(10) -0.0013(11) -0.0108(11) C19 0.0453(15) 0.0298(13) 0.0256(13) -0.0043(10) -0.0009(11) -0.0132(11) O12 0.0498(11) 0.0420(10) 0.0321(10) -0.0017(8) -0.0135(9) -0.0230(9) N12 0.0371(12) 0.0266(10) 0.0263(11) -0.0062(9) -0.0043(9) -0.0144(9) C21 0.0297(13) 0.0243(11) 0.0267(13) -0.0062(10) 0.0015(10) -0.0085(10) C22 0.0314(13) 0.0234(11) 0.0254(13) -0.0069(10) 0.0020(10) -0.0105(10) C23 0.0413(15) 0.0303(13) 0.0331(14) -0.0103(11) -0.0050(12) -0.0166(12) C24 0.0587(18) 0.0311(14) 0.0284(14) -0.0060(11) -0.0135(13) -0.0142(13) C25 0.0608(19) 0.0303(14) 0.0277(14) -0.0056(11) -0.0038(13) -0.0189(13) C26 0.0435(15) 0.0318(13) 0.0302(14) -0.0066(11) 0.0005(12) -0.0190(12) C27 0.0276(13) 0.0257(12) 0.0308(14) -0.0078(10) 0.0015(11) -0.0106(10) O21 0.0426(10) 0.0300(9) 0.0308(10) -0.0028(7) -0.0073(8) -0.0166(8) N21 0.0496(14) 0.0291(12) 0.0328(13) -0.0026(10) -0.0086(11) -0.0206(10) C28 0.0318(13) 0.0319(13) 0.0317(14) -0.0064(11) -0.0004(11) -0.0153(11) C29 0.0389(15) 0.0423(15) 0.0359(15) -0.0054(12) -0.0051(12) -0.0199(12) O22 0.0677(13) 0.0351(10) 0.0384(11) -0.0008(8) -0.0144(10) -0.0297(9) N22 0.0356(12) 0.0253(10) 0.0311(12) -0.0010(9) -0.0057(9) -0.0151(9) C31 0.0325(13) 0.0281(12) 0.0267(13) -0.0072(10) 0.0052(11) -0.0117(10) C32 0.0312(13) 0.0279(12) 0.0254(13) -0.0057(10) 0.0040(10) -0.0106(10) C33 0.0462(16) 0.0309(14) 0.0294(14) -0.0023(11) 0.0004(12) -0.0184(12) C34 0.0478(17) 0.0403(15) 0.0326(15) -0.0079(12) -0.0012(12) -0.0262(13) C35 0.0449(16) 0.0449(16) 0.0298(15) -0.0073(12) -0.0048(13) -0.0173(13) C36 0.0453(16) 0.0303(13) 0.0304(14) -0.0014(11) -0.0058(12) -0.0153(12) C37 0.0348(14) 0.0268(12) 0.0272(13) -0.0056(10) 0.0012(11) -0.0114(11) O31 0.0477(11) 0.0346(10) 0.0323(10) -0.0012(8) -0.0086(8) -0.0208(8) N31 0.0482(14) 0.0334(12) 0.0320(13) 0.0010(10) -0.0114(11) -0.0204(11) C38 0.0417(15) 0.0262(12) 0.0316(14) -0.0064(11) 0.0002(12) -0.0113(11) C39 0.0542(18) 0.0351(14) 0.0421(16) -0.0069(12) -0.0043(14) -0.0221(13) O32 0.0666(13) 0.0341(10) 0.0342(11) 0.0022(8) -0.0119(10) -0.0220(9) N32 0.0410(13) 0.0269(11) 0.0289(12) -0.0045(9) -0.0046(10) -0.0126(9) C41 0.0270(13) 0.0266(12) 0.0284(13) -0.0026(10) -0.0046(10) -0.0081(10) C42 0.0263(12) 0.0256(12) 0.0286(13) -0.0044(10) -0.0047(10) -0.0061(10) C43 0.0298(13) 0.0293(13) 0.0317(15) -0.0065(11) -0.0020(11) -0.0072(10) C44 0.0291(13) 0.0294(13) 0.0373(15) -0.0028(11) -0.0001(12) -0.0117(11) C45 0.0333(14) 0.0309(13) 0.0443(16) -0.0086(12) -0.0036(12) -0.0140(11) C46 0.0388(15) 0.0348(14) 0.0317(15) -0.0085(11) -0.0067(12) -0.0156(12) C47 0.0296(13) 0.0264(12) 0.0326(14) -0.0074(10) -0.0022(11) -0.0084(10) O41 0.0469(11) 0.0293(9) 0.0280(9) -0.0036(7) -0.0053(8) -0.0181(8) N41 0.0480(14) 0.0301(12) 0.0295(12) -0.0066(10) -0.0066(10) -0.0167(10) C48 0.0305(13) 0.0320(13) 0.0310(14) -0.0036(11) -0.0085(11) -0.0102(11) C49 0.066(2) 0.0481(17) 0.0364(16) -0.0094(13) 0.0075(15) -0.0311(15) O42 0.0449(11) 0.0372(10) 0.0364(10) -0.0127(8) -0.0032(8) -0.0173(8) N42 0.0433(13) 0.0288(11) 0.0278(12) -0.0044(9) -0.0047(10) -0.0176(10) C51 0.0275(13) 0.0251(12) 0.0308(13) -0.0051(10) -0.0016(10) -0.0078(10) C52 0.0297(13) 0.0241(12) 0.0303(13) -0.0074(10) -0.0002(10) -0.0084(10) C53 0.0437(16) 0.0280(13) 0.0376(15) -0.0073(11) -0.0058(12) -0.0141(12) C54 0.0465(17) 0.0350(14) 0.0365(16) -0.0022(12) -0.0139(13) -0.0135(12) C55 0.0429(16) 0.0257(13) 0.0410(16) 0.0018(11) -0.0090(13) -0.0108(12) C56 0.0376(15) 0.0249(13) 0.0430(16) -0.0055(11) -0.0056(12) -0.0121(11) C57 0.0332(13) 0.0268(12) 0.0301(14) -0.0069(10) -0.0018(11) -0.0105(10) O51 0.0496(11) 0.0276(9) 0.0401(11) 0.0017(8) -0.0172(9) -0.0172(8) N51 0.0456(14) 0.0262(11) 0.0369(13) -0.0023(10) -0.0126(11) -0.0153(10) C58 0.0349(14) 0.0275(13) 0.0353(14) -0.0092(11) -0.0009(11) -0.0111(11) C59 0.0455(16) 0.0376(14) 0.0363(15) -0.0078(12) -0.0094(12) -0.0176(12) O52 0.0656(13) 0.0306(10) 0.0521(12) -0.0008(9) -0.0205(10) -0.0265(9) N52 0.0377(12) 0.0246(11) 0.0340(12) -0.0026(9) -0.0073(10) -0.0131(9) O1S 0.0860(19) 0.102(2) 0.0434(14) -0.0044(14) 0.0064(13) 0.0063(16) C1S 0.074(3) 0.085(3) 0.074(3) -0.024(2) -0.014(2) -0.003(2) C2S 0.081(3) 0.075(3) 0.076(3) 0.002(2) -0.020(2) -0.006(2) C3S 0.110(4) 0.102(3) 0.107(4) -0.056(3) 0.006(3) -0.030(3) _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 C6 1.391(3) . ? C1 N2 1.405(3) . ? C1 C2 1.417(3) . ? C2 C3 1.395(3) . ? C2 C7 1.498(3) . ? C3 C4 1.374(4) . ? C3 H3 0.92(3) . ? C4 C5 1.374(4) . ? C4 H4 0.95(3) . ? C5 C6 1.381(4) . ? C5 H5 0.92(3) . ? C6 H6 0.95(2) . ? C7 O1 1.246(3) . ? C7 N1 1.329(3) . ? N1 H1A 0.87(3) . ? N1 H1B 0.80(3) . ? C8 O2 1.210(3) . ? C8 N2 1.356(3) . ? C8 C9 1.499(3) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? N2 H2 0.92(2) . ? C11 C16 1.397(3) . ? C11 C12 1.407(3) . ? C11 N12 1.409(3) . ? C12 C13 1.397(3) . ? C12 C17 1.502(3) . ? C13 C14 1.374(3) . ? C13 H13 0.94(2) . ? C14 C15 1.380(3) . ? C14 H14 0.96(2) . ? C15 C16 1.385(3) . ? C15 H15 0.94(2) . ? C16 H16 0.96(3) . ? C17 O11 1.249(3) . ? C17 N11 1.325(3) . ? N11 H11A 0.87(3) . ? N11 H11B 0.98(3) . ? C18 O12 1.226(3) . ? C18 N12 1.357(3) . ? C18 C19 1.503(3) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? N12 H12 0.86(3) . ? C21 C26 1.398(3) . ? C21 N22 1.406(3) . ? C21 C22 1.415(3) . ? C22 C23 1.390(3) . ? C22 C27 1.499(3) . ? C23 C24 1.375(3) . ? C23 H23 0.89(2) . ? C24 C25 1.381(4) . ? C24 H24 0.93(3) . ? C25 C26 1.382(4) . ? C25 H25 0.99(3) . ? C26 H26 0.95(2) . ? C27 O21 1.247(3) . ? C27 N21 1.328(3) . ? N21 H21A 0.92(3) . ? N21 H21B 0.92(3) . ? C28 O22 1.218(3) . ? C28 N22 1.354(3) . ? C28 C29 1.504(3) . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? N22 H22 0.95(2) . ? C31 C36 1.393(3) . ? C31 N32 1.405(3) . ? C31 C32 1.416(3) . ? C32 C33 1.397(3) . ? C32 C37 1.490(3) . ? C33 C34 1.369(4) . ? C33 H33 0.93(3) . ? C34 C35 1.377(4) . ? C34 H34 0.98(3) . ? C35 C36 1.377(4) . ? C35 H35 0.94(3) . ? C36 H36 0.98(2) . ? C37 O31 1.249(3) . ? C37 N31 1.329(3) . ? N31 H31A 0.83(3) . ? N31 H31B 0.88(3) . ? C38 O32 1.224(3) . ? C38 N32 1.363(3) . ? C38 C39 1.492(3) . ? C39 H39A 0.9800 . ? C39 H39B 0.9800 . ? C39 H39C 0.9800 . ? N32 H32 0.89(3) . ? C41 C46 1.392(3) . ? C41 C42 1.406(3) . ? C41 N42 1.419(3) . ? C42 C43 1.396(3) . ? C42 C47 1.496(3) . ? C43 C44 1.380(3) . ? C43 H43 0.92(2) . ? C44 C45 1.370(4) . ? C44 H44 0.95(3) . ? C45 C46 1.377(4) . ? C45 H45 0.97(3) . ? C46 H46 0.92(2) . ? C47 O41 1.253(3) . ? C47 N41 1.328(3) . ? N41 H41A 0.97(3) . ? N41 H41B 0.97(3) . ? C48 O42 1.226(3) . ? C48 N42 1.346(3) . ? C48 C49 1.501(3) . ? C49 H49A 0.9800 . ? C49 H49B 0.9800 . ? C49 H49C 0.9800 . ? N42 H42 0.91(3) . ? C51 C56 1.401(3) . ? C51 N52 1.407(3) . ? C51 C52 1.411(3) . ? C52 C53 1.395(3) . ? C52 C57 1.497(3) . ? C53 C54 1.381(3) . ? C53 H53 0.95(3) . ? C54 C55 1.382(4) . ? C54 H54 1.02(3) . ? C55 C56 1.377(4) . ? C55 H55 0.98(3) . ? C56 H56 0.94(3) . ? C57 O51 1.248(3) . ? C57 N51 1.329(3) . ? N51 H51A 0.88(3) . ? N51 H51B 0.94(3) . ? C58 O52 1.220(3) . ? C58 N52 1.357(3) . ? C58 C59 1.502(3) . ? C59 H59A 0.9800 . ? C59 H59B 0.9800 . ? C59 H59C 0.9800 . ? N52 H52 0.90(3) . ? O1S C1S 1.430(4) . ? O1S H1S 0.8400 . ? C1S C2S 1.484(5) . ? C1S H1SA 0.9900 . ? C1S H1SB 0.9900 . ? C2S C3S 1.492(5) . ? C2S H2SA 0.9900 . ? C2S H2SB 0.9900 . ? C3S H3S1 0.9800 . ? C3S H3S2 0.9800 . ? C3S H3S3 0.9800 . ? 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 C1 N2 121.1(2) . . ? C6 C1 C2 119.8(2) . . ? N2 C1 C2 119.1(2) . . ? C3 C2 C1 117.6(2) . . ? C3 C2 C7 120.5(2) . . ? C1 C2 C7 121.8(2) . . ? C4 C3 C2 122.0(2) . . ? C4 C3 H3 115.2(18) . . ? C2 C3 H3 122.8(18) . . ? C3 C4 C5 119.7(3) . . ? C3 C4 H4 119.0(16) . . ? C5 C4 H4 121.2(16) . . ? C4 C5 C6 120.5(3) . . ? C4 C5 H5 122.2(16) . . ? C6 C5 H5 117.3(16) . . ? C5 C6 C1 120.3(2) . . ? C5 C6 H6 117.1(13) . . ? C1 C6 H6 122.5(13) . . ? O1 C7 N1 119.9(2) . . ? O1 C7 C2 121.5(2) . . ? N1 C7 C2 118.6(2) . . ? C7 N1 H1A 116.5(17) . . ? C7 N1 H1B 125(2) . . ? H1A N1 H1B 119(3) . . ? O2 C8 N2 123.5(2) . . ? O2 C8 C9 121.7(2) . . ? N2 C8 C9 114.8(2) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 N2 C1 127.7(2) . . ? C8 N2 H2 115.2(15) . . ? C1 N2 H2 115.7(15) . . ? C16 C11 C12 119.5(2) . . ? C16 C11 N12 122.1(2) . . ? C12 C11 N12 118.5(2) . . ? C13 C12 C11 118.4(2) . . ? C13 C12 C17 119.6(2) . . ? C11 C12 C17 121.9(2) . . ? C14 C13 C12 121.8(2) . . ? C14 C13 H13 119.3(14) . . ? C12 C13 H13 118.8(14) . . ? C13 C14 C15 119.4(2) . . ? C13 C14 H14 120.7(15) . . ? C15 C14 H14 119.8(15) . . ? C14 C15 C16 120.6(2) . . ? C14 C15 H15 120.8(14) . . ? C16 C15 H15 118.6(14) . . ? C15 C16 C11 120.3(2) . . ? C15 C16 H16 119.0(15) . . ? C11 C16 H16 120.7(15) . . ? O11 C17 N11 121.0(2) . . ? O11 C17 C12 121.0(2) . . ? N11 C17 C12 117.9(2) . . ? C17 N11 H11A 124.2(18) . . ? C17 N11 H11B 115.5(19) . . ? H11A N11 H11B 118(3) . . ? O12 C18 N12 123.6(2) . . ? O12 C18 C19 121.6(2) . . ? N12 C18 C19 114.9(2) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C18 N12 C11 129.5(2) . . ? C18 N12 H12 116.9(17) . . ? C11 N12 H12 113.4(17) . . ? C26 C21 N22 121.4(2) . . ? C26 C21 C22 119.0(2) . . ? N22 C21 C22 119.5(2) . . ? C23 C22 C21 118.1(2) . . ? C23 C22 C27 120.0(2) . . ? C21 C22 C27 121.9(2) . . ? C24 C23 C22 122.0(2) . . ? C24 C23 H23 119.9(15) . . ? C22 C23 H23 118.1(15) . . ? C23 C24 C25 119.7(3) . . ? C23 C24 H24 119.2(16) . . ? C25 C24 H24 121.1(15) . . ? C24 C25 C26 120.0(2) . . ? C24 C25 H25 119.4(17) . . ? C26 C25 H25 120.6(17) . . ? C25 C26 C21 120.8(2) . . ? C25 C26 H26 120.3(14) . . ? C21 C26 H26 118.8(14) . . ? O21 C27 N21 120.8(2) . . ? O21 C27 C22 121.4(2) . . ? N21 C27 C22 117.7(2) . . ? C27 N21 H21A 125.3(17) . . ? C27 N21 H21B 121.4(17) . . ? H21A N21 H21B 113(2) . . ? O22 C28 N22 123.7(2) . . ? O22 C28 C29 121.5(2) . . ? N22 C28 C29 114.8(2) . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C28 N22 C21 128.2(2) . . ? C28 N22 H22 115.4(15) . . ? C21 N22 H22 114.7(15) . . ? C36 C31 N32 121.5(2) . . ? C36 C31 C32 119.9(2) . . ? N32 C31 C32 118.5(2) . . ? C33 C32 C31 117.1(2) . . ? C33 C32 C37 120.3(2) . . ? C31 C32 C37 122.6(2) . . ? C34 C33 C32 122.6(2) . . ? C34 C33 H33 118.0(17) . . ? C32 C33 H33 119.2(17) . . ? C33 C34 C35 119.2(3) . . ? C33 C34 H34 120.2(15) . . ? C35 C34 H34 120.5(15) . . ? C34 C35 C36 120.7(3) . . ? C34 C35 H35 119.4(17) . . ? C36 C35 H35 119.8(17) . . ? C35 C36 C31 120.3(2) . . ? C35 C36 H36 121.2(15) . . ? C31 C36 H36 118.5(15) . . ? O31 C37 N31 119.5(2) . . ? O31 C37 C32 121.7(2) . . ? N31 C37 C32 118.9(2) . . ? C37 N31 H31A 116.9(18) . . ? C37 N31 H31B 122.9(19) . . ? H31A N31 H31B 120(3) . . ? O32 C38 N32 123.5(2) . . ? O32 C38 C39 122.0(2) . . ? N32 C38 C39 114.5(2) . . ? C38 C39 H39A 109.5 . . ? C38 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? C38 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? C38 N32 C31 129.3(2) . . ? C38 N32 H32 112.9(19) . . ? C31 N32 H32 117.1(19) . . ? C46 C41 C42 119.8(2) . . ? C46 C41 N42 121.6(2) . . ? C42 C41 N42 118.5(2) . . ? C43 C42 C41 118.1(2) . . ? C43 C42 C47 120.1(2) . . ? C41 C42 C47 121.8(2) . . ? C44 C43 C42 121.4(3) . . ? C44 C43 H43 120.2(15) . . ? C42 C43 H43 118.3(15) . . ? C45 C44 C43 119.7(2) . . ? C45 C44 H44 120.2(15) . . ? C43 C44 H44 120.1(15) . . ? C44 C45 C46 120.6(2) . . ? C44 C45 H45 119.6(15) . . ? C46 C45 H45 119.8(16) . . ? C45 C46 C41 120.3(2) . . ? C45 C46 H46 121.2(15) . . ? C41 C46 H46 118.5(16) . . ? O41 C47 N41 120.9(2) . . ? O41 C47 C42 120.9(2) . . ? N41 C47 C42 118.2(2) . . ? C47 N41 H41A 117.7(15) . . ? C47 N41 H41B 124.1(17) . . ? H41A N41 H41B 117(2) . . ? O42 C48 N42 124.0(2) . . ? O42 C48 C49 121.0(2) . . ? N42 C48 C49 115.0(2) . . ? C48 C49 H49A 109.5 . . ? C48 C49 H49B 109.5 . . ? H49A C49 H49B 109.5 . . ? C48 C49 H49C 109.5 . . ? H49A C49 H49C 109.5 . . ? H49B C49 H49C 109.5 . . ? C48 N42 C41 128.3(2) . . ? C48 N42 H42 120.4(19) . . ? C41 N42 H42 111.3(19) . . ? C56 C51 N52 121.5(2) . . ? C56 C51 C52 119.5(2) . . ? N52 C51 C52 119.0(2) . . ? C53 C52 C51 118.0(2) . . ? C53 C52 C57 119.9(2) . . ? C51 C52 C57 122.1(2) . . ? C54 C53 C52 122.2(2) . . ? C54 C53 H53 120.6(16) . . ? C52 C53 H53 117.2(16) . . ? C53 C54 C55 119.1(3) . . ? C53 C54 H54 119.1(15) . . ? C55 C54 H54 121.9(15) . . ? C56 C55 C54 120.6(2) . . ? C56 C55 H55 120.1(17) . . ? C54 C55 H55 119.3(17) . . ? C55 C56 C51 120.6(2) . . ? C55 C56 H56 119.1(16) . . ? C51 C56 H56 120.1(16) . . ? O51 C57 N51 119.8(2) . . ? O51 C57 C52 121.5(2) . . ? N51 C57 C52 118.7(2) . . ? C57 N51 H51A 122.9(17) . . ? C57 N51 H51B 122.0(18) . . ? H51A N51 H51B 115(2) . . ? O52 C58 N52 124.5(2) . . ? O52 C58 C59 121.1(2) . . ? N52 C58 C59 114.4(2) . . ? C58 C59 H59A 109.5 . . ? C58 C59 H59B 109.5 . . ? H59A C59 H59B 109.5 . . ? C58 C59 H59C 109.5 . . ? H59A C59 H59C 109.5 . . ? H59B C59 H59C 109.5 . . ? C58 N52 C51 129.7(2) . . ? C58 N52 H52 114.5(19) . . ? C51 N52 H52 115.8(19) . . ? C1S O1S H1S 109.5 . . ? O1S C1S C2S 114.5(3) . . ? O1S C1S H1SA 108.6 . . ? C2S C1S H1SA 108.6 . . ? O1S C1S H1SB 108.6 . . ? C2S C1S H1SB 108.6 . . ? H1SA C1S H1SB 107.6 . . ? C1S C2S C3S 112.9(4) . . ? C1S C2S H2SA 109.0 . . ? C3S C2S H2SA 109.0 . . ? C1S C2S H2SB 109.0 . . ? C3S C2S H2SB 109.0 . . ? H2SA C2S H2SB 107.8 . . ? C2S C3S H3S1 109.5 . . ? C2S C3S H3S2 109.5 . . ? H3S1 C3S H3S2 109.5 . . ? C2S C3S H3S3 109.5 . . ? H3S1 C3S H3S3 109.5 . . ? H3S2 C3S H3S3 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.9(4) . . . . ? N2 C1 C2 C3 178.3(2) . . . . ? C6 C1 C2 C7 176.1(2) . . . . ? N2 C1 C2 C7 -4.7(3) . . . . ? C1 C2 C3 C4 1.4(4) . . . . ? C7 C2 C3 C4 -175.6(3) . . . . ? C2 C3 C4 C5 -0.7(5) . . . . ? C3 C4 C5 C6 -0.5(4) . . . . ? C4 C5 C6 C1 0.9(4) . . . . ? N2 C1 C6 C5 -179.4(2) . . . . ? C2 C1 C6 C5 -0.2(4) . . . . ? C3 C2 C7 O1 -172.8(2) . . . . ? C1 C2 C7 O1 10.3(4) . . . . ? C3 C2 C7 N1 8.5(4) . . . . ? C1 C2 C7 N1 -168.3(2) . . . . ? O2 C8 N2 C1 1.4(4) . . . . ? C9 C8 N2 C1 -178.8(2) . . . . ? C6 C1 N2 C8 -23.1(4) . . . . ? C2 C1 N2 C8 157.6(2) . . . . ? C16 C11 C12 C13 0.0(3) . . . . ? N12 C11 C12 C13 -179.3(2) . . . . ? C16 C11 C12 C17 179.0(2) . . . . ? N12 C11 C12 C17 -0.3(3) . . . . ? C11 C12 C13 C14 -0.1(4) . . . . ? C17 C12 C13 C14 -179.2(2) . . . . ? C12 C13 C14 C15 0.1(4) . . . . ? C13 C14 C15 C16 0.1(4) . . . . ? C14 C15 C16 C11 -0.2(4) . . . . ? C12 C11 C16 C15 0.1(4) . . . . ? N12 C11 C16 C15 179.4(2) . . . . ? C13 C12 C17 O11 157.8(2) . . . . ? C11 C12 C17 O11 -21.2(4) . . . . ? C13 C12 C17 N11 -20.2(3) . . . . ? C11 C12 C17 N11 160.9(2) . . . . ? O12 C18 N12 C11 1.4(4) . . . . ? C19 C18 N12 C11 -179.1(2) . . . . ? C16 C11 N12 C18 10.8(4) . . . . ? C12 C11 N12 C18 -169.9(2) . . . . ? C26 C21 C22 C23 7.0(3) . . . . ? N22 C21 C22 C23 -174.4(2) . . . . ? C26 C21 C22 C27 -173.6(2) . . . . ? N22 C21 C22 C27 5.0(3) . . . . ? C21 C22 C23 C24 -3.5(4) . . . . ? C27 C22 C23 C24 177.1(2) . . . . ? C22 C23 C24 C25 -2.1(4) . . . . ? C23 C24 C25 C26 4.0(4) . . . . ? C24 C25 C26 C21 -0.3(4) . . . . ? N22 C21 C26 C25 176.2(2) . . . . ? C22 C21 C26 C25 -5.2(4) . . . . ? C23 C22 C27 O21 164.3(2) . . . . ? C21 C22 C27 O21 -15.1(4) . . . . ? C23 C22 C27 N21 -16.7(3) . . . . ? C21 C22 C27 N21 163.9(2) . . . . ? O22 C28 N22 C21 2.4(4) . . . . ? C29 C28 N22 C21 -177.3(2) . . . . ? C26 C21 N22 C28 -20.1(4) . . . . ? C22 C21 N22 C28 161.3(2) . . . . ? C36 C31 C32 C33 -3.7(4) . . . . ? N32 C31 C32 C33 177.3(2) . . . . ? C36 C31 C32 C37 176.5(2) . . . . ? N32 C31 C32 C37 -2.6(3) . . . . ? C31 C32 C33 C34 2.2(4) . . . . ? C37 C32 C33 C34 -177.9(2) . . . . ? C32 C33 C34 C35 0.6(4) . . . . ? C33 C34 C35 C36 -2.0(4) . . . . ? C34 C35 C36 C31 0.5(4) . . . . ? N32 C31 C36 C35 -178.6(2) . . . . ? C32 C31 C36 C35 2.4(4) . . . . ? C33 C32 C37 O31 -170.9(2) . . . . ? C31 C32 C37 O31 9.0(4) . . . . ? C33 C32 C37 N31 10.1(4) . . . . ? C31 C32 C37 N31 -170.0(2) . . . . ? O32 C38 N32 C31 -2.2(4) . . . . ? C39 C38 N32 C31 178.4(2) . . . . ? C36 C31 N32 C38 11.1(4) . . . . ? C32 C31 N32 C38 -169.9(2) . . . . ? C46 C41 C42 C43 1.1(4) . . . . ? N42 C41 C42 C43 177.7(2) . . . . ? C46 C41 C42 C47 -176.0(2) . . . . ? N42 C41 C42 C47 0.7(3) . . . . ? C41 C42 C43 C44 0.2(4) . . . . ? C47 C42 C43 C44 177.3(2) . . . . ? C42 C43 C44 C45 -1.4(4) . . . . ? C43 C44 C45 C46 1.4(4) . . . . ? C44 C45 C46 C41 -0.2(4) . . . . ? C42 C41 C46 C45 -1.1(4) . . . . ? N42 C41 C46 C45 -177.6(2) . . . . ? C43 C42 C47 O41 -156.0(2) . . . . ? C41 C42 C47 O41 21.1(4) . . . . ? C43 C42 C47 N41 23.1(3) . . . . ? C41 C42 C47 N41 -159.9(2) . . . . ? O42 C48 N42 C41 -2.7(4) . . . . ? C49 C48 N42 C41 177.8(2) . . . . ? C46 C41 N42 C48 -21.7(4) . . . . ? C42 C41 N42 C48 161.7(2) . . . . ? C56 C51 C52 C53 2.6(4) . . . . ? N52 C51 C52 C53 -178.9(2) . . . . ? C56 C51 C52 C57 -176.1(2) . . . . ? N52 C51 C52 C57 2.4(4) . . . . ? C51 C52 C53 C54 -0.9(4) . . . . ? C57 C52 C53 C54 177.8(2) . . . . ? C52 C53 C54 C55 -1.3(4) . . . . ? C53 C54 C55 C56 1.8(4) . . . . ? C54 C55 C56 C51 -0.1(4) . . . . ? N52 C51 C56 C55 179.4(2) . . . . ? C52 C51 C56 C55 -2.1(4) . . . . ? C53 C52 C57 O51 174.7(2) . . . . ? C51 C52 C57 O51 -6.6(4) . . . . ? C53 C52 C57 N51 -6.3(4) . . . . ? C51 C52 C57 N51 172.4(2) . . . . ? O52 C58 N52 C51 0.7(4) . . . . ? C59 C58 N52 C51 179.4(2) . . . . ? C56 C51 N52 C58 -4.7(4) . . . . ? C52 C51 N52 C58 176.8(2) . . . . ? O1S C1S C2S C3S -58.7(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A O31 0.87(3) 2.08(3) 2.949(3) 179(3) . N1 H1B O52 0.80(3) 2.17(3) 2.954(3) 167(3) 1_445 C3 H3 O52 0.92(3) 2.34(3) 3.249(3) 168(2) 1_445 N11 H11B O41 0.98(3) 1.94(3) 2.914(3) 173(3) 2_666 N11 H11A O2 0.87(3) 1.99(3) 2.861(3) 177(3) 1_556 C13 H13 O2 0.94(2) 2.42(2) 3.143(3) 132.9(18) 1_556 N21 H21B O51 0.92(3) 1.98(3) 2.898(3) 172(2) . N21 H21A O12 0.92(3) 2.05(3) 2.963(3) 173(2) 1_655 C23 H23 O12 0.89(2) 2.54(2) 3.297(3) 143.4(19) 1_655 N31 H31A O1 0.83(3) 2.14(3) 2.968(3) 174(3) . N31 H31B O22 0.88(3) 2.08(3) 2.951(3) 170(3) . C33 H33 O22 0.93(3) 2.40(3) 3.261(3) 155(2) . N41 H41A O11 0.97(3) 1.98(3) 2.941(3) 174(2) 2_666 N41 H41B O32 0.97(3) 1.93(3) 2.897(3) 176(3) 2_656 C43 H43 O32 0.92(2) 2.53(2) 3.250(3) 134.7(19) 2_656 N51 H51B O21 0.94(3) 1.95(3) 2.885(3) 172(3) . N51 H51A O42 0.88(3) 2.18(3) 3.036(3) 166(2) 2_665 C53 H53 O42 0.95(3) 2.39(3) 3.333(3) 179(2) 2_665 O1S H1S O42 0.84 2.04 2.875(3) 173.1 1_556 C25 H25 O1S 0.99(3) 2.51(3) 3.463(4) 162(2) . N2 H2 O1 0.92(2) 1.87(2) 2.613(3) 137(2) . N12 H12 O11 0.86(3) 1.92(3) 2.644(3) 141(2) . N22 H22 O21 0.95(2) 1.86(2) 2.641(2) 137(2) . N32 H32 O31 0.89(3) 1.90(3) 2.623(3) 137(3) . N42 H42 O41 0.91(3) 1.87(3) 2.631(3) 140(3) . N52 H52 O51 0.90(3) 1.87(3) 2.609(3) 138(3) . _diffrn_measured_fraction_theta_max 0.929 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.519 _refine_diff_density_min -0.365 _refine_diff_density_rms 0.055 data_[(AABA)6.(1-BuOH)] _database_code_depnum_ccdc_archive 'CCDC 294941' _audit_creation_method SHELXL-97 _chemical_name_systematic ; o-Acetamidobenzamide 1-butanol solvate (6/1) ; _chemical_name_common (C9H10N2O2)6.(C4H10O) _chemical_melting_point ? _chemical_formula_moiety 'C9.67 H11.67 N2 O2.17' _chemical_formula_sum 'C9.67 H11.67 N2 O2.17' _chemical_formula_weight 190.54 _exptl_special_details ; Crystals of this solvate decomposed very quickly, even under perfluoropolyether oil. The crystal used for data collection was the best one looked at although it appears to have cracked. Treatment as a twin (SAINT v6.36A) was attempted but this did not improvme the data or refinement. ; loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.145(6) _cell_length_b 18.334(12) _cell_length_c 19.059(12) _cell_angle_alpha 67.290(10) _cell_angle_beta 86.635(11) _cell_angle_gamma 81.875(11) _cell_volume 2918(3) _cell_formula_units_Z 12 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5210 _cell_measurement_theta_min 2.250 _cell_measurement_theta_max 28.163 _exptl_crystal_description Block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.59 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.301 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1212 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3513 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS v 2.03' _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 SMART APEX diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% None _diffrn_reflns_number 24359 _diffrn_reflns_av_R_equivalents 0.155 _diffrn_reflns_av_sigmaI/netI 0.1772 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.32 _diffrn_reflns_theta_max 28.47 _reflns_number_total 12624 _reflns_number_gt 5333 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _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^)+(0.1636P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary 'direct methods' _atom_sites_solution_secondary 'differnce Fourier synthesis' _atom_sites_solution_hydrogens 'methyl H found from delta F; others geometrically placed' _refine_ls_hydrogen_treatment 'methyl H rigid rotor model; others riding' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 12623 _refine_ls_number_parameters 755 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1938 _refine_ls_R_factor_gt 0.1000 _refine_ls_wR_factor_ref 0.2935 _refine_ls_wR_factor_gt 0.2394 _refine_ls_goodness_of_fit_ref 0.886 _refine_ls_restrained_S_all 0.886 _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 -0.0037(5) 0.3163(2) 0.1252(2) 0.0325(9) Uani 1 1 d . . . C2 C -0.0460(5) 0.2495(2) 0.1867(2) 0.0344(10) Uani 1 1 d . . . C3 C -0.1382(5) 0.2028(2) 0.1717(2) 0.0383(10) Uani 1 1 d . . . H3A H -0.1695 0.1584 0.2126 0.046 Uiso 1 1 calc R . . C4 C -0.1849(5) 0.2192(2) 0.0990(2) 0.0439(11) Uani 1 1 d . . . H4A H -0.2484 0.1870 0.0901 0.053 Uiso 1 1 calc R . . C5 C -0.1382(5) 0.2834(2) 0.0394(2) 0.0445(12) Uani 1 1 d . . . H5A H -0.1675 0.2940 -0.0110 0.053 Uiso 1 1 calc R . . C6 C -0.0498(5) 0.3322(2) 0.0516(2) 0.0397(11) Uani 1 1 d . . . H6A H -0.0203 0.3766 0.0101 0.048 Uiso 1 1 calc R . . C7 C 0.0083(5) 0.2275(2) 0.2651(2) 0.0336(10) Uani 1 1 d . . . O1 O 0.0588(4) 0.27621(15) 0.28501(14) 0.0413(8) Uani 1 1 d . . . N1 N 0.0027(4) 0.15295(18) 0.31465(18) 0.0421(10) Uani 1 1 d . . . H1A H 0.0347 0.1381 0.3614 0.050 Uiso 1 1 calc R . . H1B H -0.0329 0.1186 0.3006 0.050 Uiso 1 1 calc R . . C8 C 0.1531(5) 0.4257(2) 0.0906(2) 0.0384(10) Uani 1 1 d . . . C9 C 0.2218(5) 0.4733(2) 0.1252(2) 0.0417(11) Uani 1 1 d . . . H9A H 0.1563 0.5228 0.1180 0.062 Uiso 1 1 calc R . . H9B H 0.3171 0.4861 0.1006 0.062 Uiso 1 1 calc R . . H9C H 0.2368 0.4422 0.1797 0.062 Uiso 1 1 calc R . . O2 O 0.1645(4) 0.43891(19) 0.02237(15) 0.0594(10) Uani 1 1 d . . . N2 N 0.0807(4) 0.36734(17) 0.14016(17) 0.0362(9) Uani 1 1 d . . . H2A H 0.0870 0.3602 0.1883 0.043 Uiso 1 1 calc R . . C11 C 0.0939(5) 0.5059(2) 0.7359(2) 0.0321(10) Uani 1 1 d . . . C12 C 0.1699(5) 0.4889(2) 0.8041(2) 0.0328(10) Uani 1 1 d . . . C13 C 0.1605(5) 0.4158(2) 0.8636(2) 0.0390(11) Uani 1 1 d . . . H13A H 0.2101 0.4038 0.9100 0.047 Uiso 1 1 calc R . . C14 C 0.0804(5) 0.3600(2) 0.8568(2) 0.0387(10) Uani 1 1 d . . . H14A H 0.0760 0.3103 0.8980 0.046 Uiso 1 1 calc R . . C15 C 0.0079(5) 0.3770(2) 0.7906(2) 0.0394(11) Uani 1 1 d . . . H15A H -0.0469 0.3388 0.7859 0.047 Uiso 1 1 calc R . . C16 C 0.0132(5) 0.4494(2) 0.7299(2) 0.0364(10) Uani 1 1 d . . . H16A H -0.0382 0.4605 0.6843 0.044 Uiso 1 1 calc R . . C17 C 0.2588(5) 0.5473(2) 0.8133(2) 0.0333(10) Uani 1 1 d . . . O11 O 0.3018(3) 0.60256(16) 0.75671(15) 0.0424(8) Uani 1 1 d . . . N11 N 0.2930(4) 0.53786(19) 0.88321(18) 0.0420(10) Uani 1 1 d . . . H11A H 0.3467 0.5707 0.8902 0.050 Uiso 1 1 calc R . . H11B H 0.2621 0.4988 0.9226 0.050 Uiso 1 1 calc R . . C18 C 0.0348(5) 0.6118(2) 0.6073(2) 0.0338(10) Uani 1 1 d . . . C19 C 0.0817(5) 0.6905(2) 0.5555(2) 0.0390(11) Uani 1 1 d . . . H19A H 0.1882 0.6892 0.5605 0.058 Uiso 1 1 calc R . . H19B H 0.0285 0.7333 0.5695 0.058 Uiso 1 1 calc R . . H19C H 0.0588 0.7004 0.5027 0.058 Uiso 1 1 calc R . . O12 O -0.0590(4) 0.58128(16) 0.58876(15) 0.0450(8) Uani 1 1 d . . . N12 N 0.1067(4) 0.57825(17) 0.67466(17) 0.0360(9) Uani 1 1 d . . . H12A H 0.1718 0.6062 0.6810 0.043 Uiso 1 1 calc R . . C21 C 0.6175(5) 0.4237(2) 0.4816(2) 0.0321(9) Uani 1 1 d . . . C22 C 0.7187(5) 0.4724(2) 0.4887(2) 0.0325(10) Uani 1 1 d . . . C23 C 0.7994(5) 0.4452(2) 0.5550(2) 0.0408(11) Uani 1 1 d . . . H23A H 0.8700 0.4764 0.5596 0.049 Uiso 1 1 calc R . . C24 C 0.7813(5) 0.3748(2) 0.6145(2) 0.0459(12) Uani 1 1 d . . . H24A H 0.8405 0.3571 0.6587 0.055 Uiso 1 1 calc R . . C25 C 0.6756(5) 0.3299(2) 0.6091(2) 0.0412(11) Uani 1 1 d . . . H25A H 0.6581 0.2827 0.6509 0.049 Uiso 1 1 calc R . . C26 C 0.5964(5) 0.3536(2) 0.5434(2) 0.0399(11) Uani 1 1 d . . . H26A H 0.5259 0.3218 0.5399 0.048 Uiso 1 1 calc R . . C27 C 0.7393(5) 0.5505(2) 0.4264(2) 0.0336(10) Uani 1 1 d . . . O21 O 0.6835(3) 0.57085(14) 0.36215(15) 0.0397(7) Uani 1 1 d . . . N21 N 0.8153(4) 0.59989(18) 0.44072(18) 0.0413(9) Uani 1 1 d . . . H21A H 0.8262 0.6467 0.4051 0.050 Uiso 1 1 calc R . . H21B H 0.8546 0.5858 0.4858 0.050 Uiso 1 1 calc R . . C28 C 0.4664(5) 0.4036(2) 0.3878(2) 0.0376(10) Uani 1 1 d . . . C29 C 0.3886(5) 0.4495(3) 0.3135(2) 0.0447(11) Uani 1 1 d . . . H29A H 0.4118 0.4209 0.2794 0.067 Uiso 1 1 calc R . . H29B H 0.4214 0.5024 0.2902 0.067 Uiso 1 1 calc R . . H29C H 0.2817 0.4554 0.3224 0.067 Uiso 1 1 calc R . . O22 O 0.4606(4) 0.33220(16) 0.42202(16) 0.0550(9) Uani 1 1 d . . . N22 N 0.5390(4) 0.44747(18) 0.41402(17) 0.0359(9) Uani 1 1 d . . . H22A H 0.5362 0.4982 0.3842 0.043 Uiso 1 1 calc R . . C31 C 0.3740(5) 0.0411(2) 0.5795(2) 0.0367(10) Uani 1 1 d . . . C32 C 0.3351(5) 0.1235(2) 0.5355(2) 0.0345(10) Uani 1 1 d . . . C33 C 0.3806(5) 0.1784(2) 0.5608(2) 0.0398(11) Uani 1 1 d . . . H33A H 0.3547 0.2337 0.5319 0.048 Uiso 1 1 calc R . . C34 C 0.4615(5) 0.1558(2) 0.6257(2) 0.0429(12) Uani 1 1 d . . . H34A H 0.4901 0.1946 0.6419 0.051 Uiso 1 1 calc R . . C35 C 0.5008(5) 0.0751(2) 0.6674(2) 0.0443(12) Uani 1 1 d . . . H35A H 0.5587 0.0586 0.7119 0.053 Uiso 1 1 calc R . . C36 C 0.4570(5) 0.0188(2) 0.6449(2) 0.0445(12) Uani 1 1 d . . . H36A H 0.4839 -0.0362 0.6745 0.053 Uiso 1 1 calc R . . C37 C 0.2495(5) 0.1512(2) 0.4639(2) 0.0369(10) Uani 1 1 d . . . O31 O 0.1617(4) 0.10932(15) 0.45411(15) 0.0459(8) Uani 1 1 d . . . N31 N 0.2645(4) 0.22303(18) 0.41146(18) 0.0425(9) Uani 1 1 d . . . H31A H 0.2125 0.2416 0.3693 0.051 Uiso 1 1 calc R . . H31B H 0.3264 0.2520 0.4189 0.051 Uiso 1 1 calc R . . C38 C 0.3551(5) -0.0951(2) 0.5852(2) 0.0376(10) Uani 1 1 d . . . C39 C 0.2850(6) -0.1368(2) 0.5447(2) 0.0461(12) Uani 1 1 d . . . H39A H 0.3024 -0.1946 0.5735 0.069 Uiso 1 1 calc R . . H39B H 0.3282 -0.1241 0.4938 0.069 Uiso 1 1 calc R . . H39C H 0.1784 -0.1192 0.5405 0.069 Uiso 1 1 calc R . . O32 O 0.4357(4) -0.13140(16) 0.63935(17) 0.0559(9) Uani 1 1 d . . . N32 N 0.3242(4) -0.01444(18) 0.55557(18) 0.0416(9) Uani 1 1 d . . . H32 H 0.2649 0.0057 0.5160 0.050 Uiso 1 1 calc R . . C41 C 0.3985(5) 0.2302(2) 0.0746(2) 0.0362(10) Uani 1 1 d . . . C42 C 0.4105(5) 0.2312(2) 0.1478(2) 0.0330(9) Uani 1 1 d . . . C43 C 0.3515(5) 0.1722(2) 0.2096(2) 0.0384(10) Uani 1 1 d . . . H43A H 0.3591 0.1718 0.2593 0.046 Uiso 1 1 calc R . . C44 C 0.2820(5) 0.1146(2) 0.1997(2) 0.0437(11) Uani 1 1 d . . . H44A H 0.2426 0.0749 0.2423 0.052 Uiso 1 1 calc R . . C45 C 0.2702(5) 0.1148(3) 0.1280(3) 0.0470(12) Uani 1 1 d . . . H45A H 0.2228 0.0752 0.1212 0.056 Uiso 1 1 calc R . . C46 C 0.3270(5) 0.1723(2) 0.0659(2) 0.0432(11) Uani 1 1 d . . . H46A H 0.3170 0.1724 0.0165 0.052 Uiso 1 1 calc R . . C47 C 0.4839(5) 0.2938(2) 0.1596(2) 0.0347(10) Uani 1 1 d . . . O41 O 0.5032(3) 0.35695(15) 0.10534(15) 0.0416(8) Uani 1 1 d . . . N41 N 0.5281(4) 0.28014(19) 0.22908(18) 0.0428(9) Uani 1 1 d . . . H41A H 0.5717 0.3159 0.2373 0.051 Uiso 1 1 calc R . . H41B H 0.5138 0.2353 0.2669 0.051 Uiso 1 1 calc R . . C48 C 0.5133(5) 0.2820(2) -0.0527(2) 0.0371(10) Uani 1 1 d . . . C49 C 0.5595(6) 0.3570(2) -0.1136(2) 0.0458(12) Uani 1 1 d . . . H49A H 0.4911 0.3760 -0.1566 0.069 Uiso 1 1 calc R . . H49B H 0.6598 0.3454 -0.1312 0.069 Uiso 1 1 calc R . . H49C H 0.5577 0.3983 -0.0926 0.069 Uiso 1 1 calc R . . O42 O 0.5301(4) 0.21897(17) -0.06257(17) 0.0521(9) Uani 1 1 d . . . N42 N 0.4547(4) 0.29008(19) 0.01028(18) 0.0398(9) Uani 1 1 d . . . H42A H 0.4505 0.3376 0.0121 0.048 Uiso 1 1 calc R . . C51 C 0.7978(5) 0.9212(2) 0.2205(2) 0.0345(10) Uani 1 1 d . . . C52 C 0.7313(5) 0.8626(2) 0.2070(2) 0.0343(10) Uani 1 1 d . . . C53 C 0.6377(6) 0.8861(2) 0.1455(2) 0.0487(13) Uani 1 1 d . . . H53A H 0.5953 0.8470 0.1351 0.058 Uiso 1 1 calc R . . C54 C 0.6050(6) 0.9655(3) 0.0989(2) 0.0616(16) Uani 1 1 d . . . H54A H 0.5392 0.9805 0.0575 0.074 Uiso 1 1 calc R . . C55 C 0.6670(6) 1.0226(3) 0.1122(3) 0.0562(14) Uani 1 1 d . . . H55A H 0.6431 1.0772 0.0804 0.067 Uiso 1 1 calc R . . C56A C 0.7640(5) 1.0011(2) 0.1717(2) 0.0479(13) Uani 1 1 d . . . H56 H 0.8084 1.0411 0.1797 0.058 Uiso 1 1 calc R . . C57 C 0.7560(5) 0.7763(2) 0.2606(2) 0.0367(10) Uani 1 1 d . . . O51 O 0.8633(3) 0.74879(15) 0.30334(16) 0.0413(8) Uani 1 1 d . . . N51 N 0.6541(4) 0.73149(18) 0.25878(18) 0.0424(10) Uani 1 1 d . . . H51A H 0.6626 0.6806 0.2887 0.051 Uiso 1 1 calc R . . H51B H 0.5786 0.7528 0.2277 0.051 Uiso 1 1 calc R . . C58 C 0.9629(5) 0.9414(2) 0.3091(2) 0.0413(11) Uani 1 1 d . . . C59 C 1.0563(6) 0.8948(3) 0.3774(2) 0.0498(13) Uani 1 1 d . . . H59A H 1.1543 0.9125 0.3690 0.075 Uiso 1 1 calc R . . H59B H 1.0660 0.8380 0.3863 0.075 Uiso 1 1 calc R . . H59C H 1.0100 0.9031 0.4218 0.075 Uiso 1 1 calc R . . O52 O 0.9497(4) 1.01448(16) 0.28105(18) 0.0615(10) Uani 1 1 d . . . N52 N 0.8931(4) 0.89740(17) 0.28167(17) 0.0363(9) Uani 1 1 d . . . H52A H 0.9111 0.8455 0.3066 0.044 Uiso 1 1 calc R . . C1S C 0.7524(7) 0.1534(3) 0.8041(3) 0.0621(15) Uani 1 1 d . . . H1SA H 0.8250 0.1710 0.7624 0.075 Uiso 1 1 calc R . . H1SB H 0.6967 0.1157 0.7944 0.075 Uiso 1 1 calc R . . C2S C 0.8331(6) 0.1107(3) 0.8766(3) 0.0537(13) Uani 1 1 d . . . H2SA H 0.9009 0.0656 0.8721 0.064 Uiso 1 1 calc R . . H2SB H 0.7609 0.0882 0.9174 0.064 Uiso 1 1 calc R . . C3S C 0.9210(6) 0.1606(3) 0.9000(3) 0.0531(13) Uani 1 1 d . . . H3SA H 0.8524 0.2032 0.9088 0.064 Uiso 1 1 calc R . . H3SB H 0.9879 0.1866 0.8577 0.064 Uiso 1 1 calc R . . O1S O 0.6518(4) 0.22112(18) 0.80243(16) 0.0522(9) Uani 1 1 d . . . H1SC H 0.6211 0.2141 0.8467 0.078 Uiso 1 1 calc R . . C4S C 1.0118(6) 0.1144(3) 0.9707(3) 0.0627(15) Uani 1 1 d . . . H4S1 H 0.9469 0.0874 1.0128 0.094 Uiso 1 1 calc R . . H4S2 H 1.0623 0.1511 0.9839 0.094 Uiso 1 1 calc R . . H4S3 H 1.0851 0.0746 0.9614 0.094 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 0.049(3) 0.0230(17) 0.028(2) -0.0097(16) -0.0035(18) -0.0124(18) C2 0.055(3) 0.0232(18) 0.025(2) -0.0068(16) -0.0030(19) -0.0119(18) C3 0.059(3) 0.0242(18) 0.033(2) -0.0067(17) -0.006(2) -0.0174(19) C4 0.066(3) 0.030(2) 0.039(2) -0.0109(19) -0.011(2) -0.019(2) C5 0.072(3) 0.034(2) 0.029(2) -0.0095(18) -0.015(2) -0.015(2) C6 0.060(3) 0.034(2) 0.024(2) -0.0050(17) -0.010(2) -0.017(2) C7 0.056(3) 0.0290(19) 0.0179(18) -0.0073(15) 0.0010(18) -0.0181(19) O1 0.079(2) 0.0242(13) 0.0237(14) -0.0067(11) -0.0059(14) -0.0224(14) N1 0.074(3) 0.0283(16) 0.0239(17) -0.0019(14) -0.0044(17) -0.0284(17) C8 0.059(3) 0.0259(19) 0.028(2) -0.0027(16) -0.0056(19) -0.0164(19) C9 0.064(3) 0.0278(19) 0.037(2) -0.0113(18) -0.002(2) -0.020(2) O2 0.103(3) 0.0581(19) 0.0213(15) -0.0053(14) -0.0014(16) -0.053(2) N2 0.067(3) 0.0262(16) 0.0174(15) -0.0047(13) -0.0049(15) -0.0215(16) C11 0.055(3) 0.0237(18) 0.0215(18) -0.0086(15) 0.0025(18) -0.0182(18) C12 0.054(3) 0.0264(18) 0.0230(19) -0.0101(16) 0.0013(18) -0.0186(18) C13 0.066(3) 0.0295(19) 0.025(2) -0.0086(17) -0.005(2) -0.021(2) C14 0.062(3) 0.0245(18) 0.031(2) -0.0063(16) -0.005(2) -0.0182(19) C15 0.066(3) 0.0276(19) 0.033(2) -0.0131(17) 0.000(2) -0.027(2) C16 0.063(3) 0.0274(19) 0.025(2) -0.0107(16) -0.0009(19) -0.0243(19) C17 0.049(3) 0.0285(19) 0.025(2) -0.0093(16) -0.0053(18) -0.0162(18) O11 0.068(2) 0.0375(15) 0.0264(14) -0.0078(12) -0.0004(14) -0.0343(15) N11 0.072(3) 0.0333(17) 0.0259(17) -0.0079(15) -0.0045(17) -0.0315(18) C18 0.061(3) 0.0258(18) 0.0192(18) -0.0091(15) -0.0016(18) -0.0181(19) C19 0.064(3) 0.0263(19) 0.026(2) -0.0049(16) 0.001(2) -0.021(2) O12 0.073(2) 0.0373(15) 0.0254(15) -0.0032(12) -0.0092(14) -0.0309(15) N12 0.065(3) 0.0237(15) 0.0256(17) -0.0086(13) 0.0005(16) -0.0284(16) C21 0.049(3) 0.0261(18) 0.0226(19) -0.0063(15) -0.0010(18) -0.0182(18) C22 0.054(3) 0.0248(18) 0.0215(18) -0.0073(15) -0.0012(18) -0.0172(18) C23 0.061(3) 0.0288(19) 0.034(2) -0.0076(18) -0.006(2) -0.022(2) C24 0.076(4) 0.036(2) 0.025(2) -0.0036(18) -0.014(2) -0.023(2) C25 0.063(3) 0.033(2) 0.024(2) 0.0007(17) -0.008(2) -0.023(2) C26 0.058(3) 0.034(2) 0.028(2) -0.0058(17) 0.002(2) -0.026(2) C27 0.053(3) 0.0257(18) 0.024(2) -0.0083(16) -0.0033(18) -0.0155(19) O21 0.071(2) 0.0239(13) 0.0257(14) -0.0048(11) -0.0055(14) -0.0232(14) N21 0.072(3) 0.0252(16) 0.0277(17) -0.0026(14) -0.0097(17) -0.0274(17) C28 0.057(3) 0.033(2) 0.0233(19) -0.0054(16) -0.0019(19) -0.024(2) C29 0.063(3) 0.043(2) 0.031(2) -0.0111(19) -0.004(2) -0.023(2) O22 0.098(3) 0.0345(15) 0.0323(16) 0.0007(13) -0.0135(16) -0.0416(17) N22 0.061(3) 0.0239(15) 0.0219(16) -0.0016(13) -0.0056(16) -0.0213(16) C31 0.060(3) 0.030(2) 0.0221(19) -0.0072(16) -0.0005(19) -0.022(2) C32 0.054(3) 0.0261(18) 0.0230(19) -0.0043(16) 0.0023(18) -0.0204(19) C33 0.068(3) 0.031(2) 0.025(2) -0.0102(17) 0.009(2) -0.027(2) C34 0.075(3) 0.038(2) 0.025(2) -0.0144(18) 0.009(2) -0.036(2) C35 0.071(3) 0.043(2) 0.025(2) -0.0127(18) -0.001(2) -0.027(2) C36 0.076(4) 0.033(2) 0.026(2) -0.0072(17) -0.009(2) -0.020(2) C37 0.061(3) 0.0269(19) 0.024(2) -0.0067(16) -0.0042(19) -0.017(2) O31 0.079(2) 0.0291(14) 0.0300(15) -0.0020(12) -0.0136(15) -0.0294(15) N31 0.070(3) 0.0293(17) 0.0270(18) -0.0014(14) -0.0039(17) -0.0268(17) C38 0.059(3) 0.0258(19) 0.028(2) -0.0057(17) -0.001(2) -0.020(2) C39 0.073(4) 0.031(2) 0.037(2) -0.0080(18) -0.004(2) -0.025(2) O32 0.096(3) 0.0298(15) 0.0417(18) -0.0057(14) -0.0218(18) -0.0206(16) N32 0.077(3) 0.0255(16) 0.0246(17) -0.0050(14) -0.0086(17) -0.0231(17) C41 0.056(3) 0.0276(19) 0.031(2) -0.0119(17) -0.0069(19) -0.0182(19) C42 0.048(3) 0.0245(18) 0.030(2) -0.0116(16) -0.0031(18) -0.0127(18) C43 0.057(3) 0.032(2) 0.030(2) -0.0109(17) -0.003(2) -0.016(2) C44 0.063(3) 0.035(2) 0.037(2) -0.0117(19) -0.001(2) -0.026(2) C45 0.061(3) 0.042(2) 0.049(3) -0.022(2) 0.001(2) -0.030(2) C46 0.067(3) 0.041(2) 0.032(2) -0.0185(19) -0.003(2) -0.025(2) C47 0.049(3) 0.0305(19) 0.029(2) -0.0119(17) -0.0043(19) -0.0157(19) O41 0.071(2) 0.0283(14) 0.0288(15) -0.0078(12) -0.0055(14) -0.0253(14) N41 0.073(3) 0.0321(17) 0.0299(18) -0.0110(15) -0.0051(17) -0.0294(18) C48 0.055(3) 0.035(2) 0.027(2) -0.0122(17) -0.0049(19) -0.017(2) C49 0.069(3) 0.035(2) 0.033(2) -0.0076(18) -0.003(2) -0.020(2) O42 0.089(3) 0.0381(16) 0.0379(17) -0.0189(14) 0.0076(16) -0.0274(17) N42 0.066(3) 0.0262(16) 0.0326(19) -0.0118(15) -0.0040(17) -0.0195(17) C51 0.052(3) 0.0279(19) 0.0230(19) -0.0038(16) -0.0009(18) -0.0185(19) C52 0.055(3) 0.0255(18) 0.0234(19) -0.0051(16) -0.0002(18) -0.0220(18) C53 0.080(4) 0.039(2) 0.028(2) -0.0020(18) -0.013(2) -0.035(2) C54 0.096(4) 0.048(3) 0.031(2) 0.009(2) -0.027(3) -0.035(3) C55 0.089(4) 0.034(2) 0.037(3) 0.0062(19) -0.021(3) -0.026(2) C56A 0.077(4) 0.030(2) 0.035(2) -0.0013(18) -0.005(2) -0.031(2) C57 0.061(3) 0.0246(18) 0.027(2) -0.0070(16) -0.004(2) -0.020(2) O51 0.061(2) 0.0259(13) 0.0359(16) -0.0034(12) -0.0132(15) -0.0199(14) N51 0.073(3) 0.0250(16) 0.0310(18) -0.0037(14) -0.0135(17) -0.0260(17) C58 0.069(3) 0.0281(19) 0.027(2) -0.0037(17) -0.003(2) -0.026(2) C59 0.073(4) 0.046(2) 0.033(2) -0.008(2) -0.007(2) -0.032(2) O52 0.110(3) 0.0270(15) 0.049(2) -0.0041(14) -0.0253(19) -0.0336(17) N52 0.062(3) 0.0225(15) 0.0228(16) -0.0006(13) -0.0062(16) -0.0230(16) C1S 0.085(4) 0.064(3) 0.043(3) -0.027(3) -0.005(3) -0.008(3) C2S 0.082(4) 0.038(2) 0.043(3) -0.013(2) -0.008(3) -0.017(2) C3S 0.068(4) 0.037(2) 0.050(3) -0.007(2) -0.007(2) -0.019(2) O1S 0.069(2) 0.0544(19) 0.0293(16) -0.0093(15) -0.0036(15) -0.0128(17) C4S 0.078(4) 0.050(3) 0.058(3) -0.013(3) -0.020(3) -0.017(3) _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 C6 1.395(5) . ? C1 N2 1.411(5) . ? C1 C2 1.413(5) . ? C2 C3 1.396(5) . ? C2 C7 1.486(5) . ? C3 C4 1.378(6) . ? C3 H3A 0.9500 . ? C4 C5 1.382(5) . ? C4 H4A 0.9500 . ? C5 C6 1.377(5) . ? C5 H5A 0.9500 . ? C6 H6A 0.9500 . ? C7 O1 1.246(4) . ? C7 N1 1.334(4) . ? N1 H1A 0.8800 . ? N1 H1B 0.8800 . ? C8 O2 1.228(5) . ? C8 N2 1.350(5) . ? C8 C9 1.497(5) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? N2 H2A 0.8800 . ? C11 C16 1.395(5) . ? C11 N12 1.402(4) . ? C11 C12 1.415(5) . ? C12 C13 1.393(5) . ? C12 C17 1.498(5) . ? C13 C14 1.387(5) . ? C13 H13A 0.9500 . ? C14 C15 1.367(6) . ? C14 H14A 0.9500 . ? C15 C16 1.388(5) . ? C15 H15A 0.9500 . ? C16 H16A 0.9500 . ? C17 O11 1.251(4) . ? C17 N11 1.326(5) . ? N11 H11A 0.8800 . ? N11 H11B 0.8800 . ? C18 O12 1.224(5) . ? C18 N12 1.354(5) . ? C18 C19 1.506(5) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? N12 H12A 0.8800 . ? C21 C26 1.397(5) . ? C21 N22 1.397(5) . ? C21 C22 1.419(5) . ? C22 C23 1.381(5) . ? C22 C27 1.494(5) . ? C23 C24 1.374(5) . ? C23 H23A 0.9500 . ? C24 C25 1.387(6) . ? C24 H24A 0.9500 . ? C25 C26 1.369(6) . ? C25 H25A 0.9500 . ? C26 H26A 0.9500 . ? C27 O21 1.251(4) . ? C27 N21 1.329(5) . ? N21 H21A 0.8800 . ? N21 H21B 0.8800 . ? C28 O22 1.224(4) . ? C28 N22 1.356(5) . ? C28 C29 1.499(6) . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? N22 H22A 0.8800 . ? C31 C36 1.388(6) . ? C31 N32 1.401(5) . ? C31 C32 1.420(5) . ? C32 C33 1.392(5) . ? C32 C37 1.486(5) . ? C33 C34 1.369(6) . ? C33 H33A 0.9500 . ? C34 C35 1.388(6) . ? C34 H34A 0.9500 . ? C35 C36 1.374(6) . ? C35 H35A 0.9500 . ? C36 H36A 0.9500 . ? C37 O31 1.254(5) . ? C37 N31 1.330(4) . ? N31 H31A 0.8800 . ? N31 H31B 0.8800 . ? C38 O32 1.213(5) . ? C38 N32 1.358(5) . ? C38 C39 1.498(6) . ? C39 H39A 0.9800 . ? C39 H39B 0.9800 . ? C39 H39C 0.9800 . ? N32 H32 0.8800 . ? C41 C46 1.388(5) . ? C41 C42 1.412(5) . ? C41 N42 1.421(5) . ? C42 C43 1.399(5) . ? C42 C47 1.501(5) . ? C43 C44 1.384(5) . ? C43 H43A 0.9500 . ? C44 C45 1.375(6) . ? C44 H44A 0.9500 . ? C45 C46 1.379(6) . ? C45 H45A 0.9500 . ? C46 H46A 0.9500 . ? C47 O41 1.246(4) . ? C47 N41 1.325(5) . ? N41 H41A 0.8800 . ? N41 H41B 0.8800 . ? C48 O42 1.228(5) . ? C48 N42 1.338(5) . ? C48 C49 1.515(5) . ? C49 H49A 0.9800 . ? C49 H49B 0.9800 . ? C49 H49C 0.9800 . ? N42 H42A 0.8800 . ? C51 N52 1.388(5) . ? C51 C56A 1.400(5) . ? C51 C52 1.416(5) . ? C52 C53 1.385(6) . ? C52 C57 1.509(5) . ? C53 C54 1.380(6) . ? C53 H53A 0.9500 . ? C54 C55 1.369(6) . ? C54 H54A 0.9500 . ? C55 C56A 1.379(6) . ? C55 H55A 0.9500 . ? C56A H56 0.9500 . ? C57 O51 1.232(5) . ? C57 N51 1.336(5) . ? N51 H51A 0.8800 . ? N51 H51B 0.8800 . ? C58 O52 1.226(4) . ? C58 N52 1.358(5) . ? C58 C59 1.489(6) . ? C59 H59A 0.9800 . ? C59 H59B 0.9800 . ? C59 H59C 0.9800 . ? N52 H52A 0.8800 . ? C1S O1S 1.428(6) . ? C1S C2S 1.478(7) . ? C1S H1SA 0.9900 . ? C1S H1SB 0.9900 . ? C2S C3S 1.499(6) . ? C2S H2SA 0.9900 . ? C2S H2SB 0.9900 . ? C3S C4S 1.508(6) . ? C3S H3SA 0.9900 . ? C3S H3SB 0.9900 . ? O1S H1SC 0.8400 . ? C4S H4S1 0.9800 . ? C4S H4S2 0.9800 . ? C4S H4S3 0.9800 . ? 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 C1 N2 121.3(3) . . ? C6 C1 C2 119.9(3) . . ? N2 C1 C2 118.7(3) . . ? C3 C2 C1 118.0(3) . . ? C3 C2 C7 120.2(3) . . ? C1 C2 C7 121.7(3) . . ? C4 C3 C2 121.8(4) . . ? C4 C3 H3A 119.1 . . ? C2 C3 H3A 119.1 . . ? C3 C4 C5 119.1(4) . . ? C3 C4 H4A 120.5 . . ? C5 C4 H4A 120.5 . . ? C6 C5 C4 121.2(4) . . ? C6 C5 H5A 119.4 . . ? C4 C5 H5A 119.4 . . ? C5 C6 C1 119.9(4) . . ? C5 C6 H6A 120.1 . . ? C1 C6 H6A 120.1 . . ? O1 C7 N1 120.1(3) . . ? O1 C7 C2 121.9(3) . . ? N1 C7 C2 118.0(3) . . ? C7 N1 H1A 120.0 . . ? C7 N1 H1B 120.0 . . ? H1A N1 H1B 120.0 . . ? O2 C8 N2 123.4(4) . . ? O2 C8 C9 121.8(4) . . ? N2 C8 C9 114.8(3) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 N2 C1 128.7(3) . . ? C8 N2 H2A 115.6 . . ? C1 N2 H2A 115.6 . . ? C16 C11 N12 121.6(3) . . ? C16 C11 C12 119.6(3) . . ? N12 C11 C12 118.8(3) . . ? C13 C12 C11 118.3(3) . . ? C13 C12 C17 119.9(3) . . ? C11 C12 C17 121.8(3) . . ? C14 C13 C12 121.5(4) . . ? C14 C13 H13A 119.3 . . ? C12 C13 H13A 119.3 . . ? C15 C14 C13 119.6(3) . . ? C15 C14 H14A 120.2 . . ? C13 C14 H14A 120.2 . . ? C14 C15 C16 120.9(3) . . ? C14 C15 H15A 119.6 . . ? C16 C15 H15A 119.6 . . ? C15 C16 C11 120.1(4) . . ? C15 C16 H16A 120.0 . . ? C11 C16 H16A 120.0 . . ? O11 C17 N11 120.8(3) . . ? O11 C17 C12 121.0(3) . . ? N11 C17 C12 118.2(3) . . ? C17 N11 H11A 120.0 . . ? C17 N11 H11B 120.0 . . ? H11A N11 H11B 120.0 . . ? O12 C18 N12 123.9(3) . . ? O12 C18 C19 122.0(3) . . ? N12 C18 C19 114.1(3) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C18 N12 C11 130.2(3) . . ? C18 N12 H12A 114.9 . . ? C11 N12 H12A 114.9 . . ? C26 C21 N22 121.4(3) . . ? C26 C21 C22 118.9(3) . . ? N22 C21 C22 119.6(3) . . ? C23 C22 C21 117.9(3) . . ? C23 C22 C27 120.6(3) . . ? C21 C22 C27 121.5(3) . . ? C24 C23 C22 122.5(4) . . ? C24 C23 H23A 118.7 . . ? C22 C23 H23A 118.7 . . ? C23 C24 C25 119.2(4) . . ? C23 C24 H24A 120.4 . . ? C25 C24 H24A 120.4 . . ? C26 C25 C24 120.1(4) . . ? C26 C25 H25A 120.0 . . ? C24 C25 H25A 120.0 . . ? C25 C26 C21 121.1(4) . . ? C25 C26 H26A 119.4 . . ? C21 C26 H26A 119.4 . . ? O21 C27 N21 119.8(3) . . ? O21 C27 C22 121.3(3) . . ? N21 C27 C22 118.9(3) . . ? C27 N21 H21A 120.0 . . ? C27 N21 H21B 120.0 . . ? H21A N21 H21B 120.0 . . ? O22 C28 N22 123.5(4) . . ? O22 C28 C29 121.5(4) . . ? N22 C28 C29 114.9(3) . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C28 N22 C21 129.2(3) . . ? C28 N22 H22A 115.4 . . ? C21 N22 H22A 115.4 . . ? C36 C31 N32 122.7(3) . . ? C36 C31 C32 118.9(3) . . ? N32 C31 C32 118.3(3) . . ? C33 C32 C31 118.2(4) . . ? C33 C32 C37 120.3(3) . . ? C31 C32 C37 121.5(3) . . ? C34 C33 C32 122.4(4) . . ? C34 C33 H33A 118.8 . . ? C32 C33 H33A 118.8 . . ? C33 C34 C35 118.7(4) . . ? C33 C34 H34A 120.6 . . ? C35 C34 H34A 120.6 . . ? C36 C35 C34 120.8(4) . . ? C36 C35 H35A 119.6 . . ? C34 C35 H35A 119.6 . . ? C35 C36 C31 120.9(4) . . ? C35 C36 H36A 119.5 . . ? C31 C36 H36A 119.5 . . ? O31 C37 N31 120.7(4) . . ? O31 C37 C32 121.0(3) . . ? N31 C37 C32 118.3(3) . . ? C37 N31 H31A 120.0 . . ? C37 N31 H31B 120.0 . . ? H31A N31 H31B 120.0 . . ? O32 C38 N32 123.2(4) . . ? O32 C38 C39 121.8(4) . . ? N32 C38 C39 115.0(4) . . ? C38 C39 H39A 109.5 . . ? C38 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? C38 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? C38 N32 C31 128.7(4) . . ? C38 N32 H32 115.6 . . ? C31 N32 H32 115.6 . . ? C46 C41 C42 119.7(4) . . ? C46 C41 N42 120.5(3) . . ? C42 C41 N42 119.8(3) . . ? C43 C42 C41 118.3(3) . . ? C43 C42 C47 120.3(3) . . ? C41 C42 C47 121.4(3) . . ? C44 C43 C42 121.1(4) . . ? C44 C43 H43A 119.4 . . ? C42 C43 H43A 119.4 . . ? C45 C44 C43 119.8(4) . . ? C45 C44 H44A 120.1 . . ? C43 C44 H44A 120.1 . . ? C44 C45 C46 120.4(4) . . ? C44 C45 H45A 119.8 . . ? C46 C45 H45A 119.8 . . ? C45 C46 C41 120.7(4) . . ? C45 C46 H46A 119.6 . . ? C41 C46 H46A 119.6 . . ? O41 C47 N41 120.9(3) . . ? O41 C47 C42 120.7(3) . . ? N41 C47 C42 118.4(3) . . ? C47 N41 H41A 120.0 . . ? C47 N41 H41B 120.0 . . ? H41A N41 H41B 120.0 . . ? O42 C48 N42 124.0(4) . . ? O42 C48 C49 120.5(4) . . ? N42 C48 C49 115.6(4) . . ? C48 C49 H49A 109.5 . . ? C48 C49 H49B 109.5 . . ? H49A C49 H49B 109.5 . . ? C48 C49 H49C 109.5 . . ? H49A C49 H49C 109.5 . . ? H49B C49 H49C 109.5 . . ? C48 N42 C41 127.0(3) . . ? C48 N42 H42A 116.5 . . ? C41 N42 H42A 116.5 . . ? N52 C51 C56A 122.6(3) . . ? N52 C51 C52 118.9(3) . . ? C56A C51 C52 118.5(4) . . ? C53 C52 C51 119.0(3) . . ? C53 C52 C57 120.1(3) . . ? C51 C52 C57 120.9(3) . . ? C54 C53 C52 121.1(4) . . ? C54 C53 H53A 119.4 . . ? C52 C53 H53A 119.4 . . ? C55 C54 C53 120.2(4) . . ? C55 C54 H54A 119.9 . . ? C53 C54 H54A 119.9 . . ? C54 C55 C56A 120.1(4) . . ? C54 C55 H55A 119.9 . . ? C56A C55 H55A 119.9 . . ? C55 C56A C51 120.9(4) . . ? C55 C56A H56 119.5 . . ? C51 C56A H56 119.5 . . ? O51 C57 N51 122.1(3) . . ? O51 C57 C52 122.1(3) . . ? N51 C57 C52 115.8(4) . . ? C57 N51 H51A 120.0 . . ? C57 N51 H51B 120.0 . . ? H51A N51 H51B 120.0 . . ? O52 C58 N52 123.2(4) . . ? O52 C58 C59 121.5(4) . . ? N52 C58 C59 115.3(3) . . ? C58 C59 H59A 109.5 . . ? C58 C59 H59B 109.5 . . ? H59A C59 H59B 109.5 . . ? C58 C59 H59C 109.5 . . ? H59A C59 H59C 109.5 . . ? H59B C59 H59C 109.5 . . ? C58 N52 C51 130.3(3) . . ? C58 N52 H52A 114.9 . . ? C51 N52 H52A 114.9 . . ? O1S C1S C2S 114.3(4) . . ? O1S C1S H1SA 108.7 . . ? C2S C1S H1SA 108.7 . . ? O1S C1S H1SB 108.7 . . ? C2S C1S H1SB 108.7 . . ? H1SA C1S H1SB 107.6 . . ? C1S C2S C3S 115.1(4) . . ? C1S C2S H2SA 108.5 . . ? C3S C2S H2SA 108.5 . . ? C1S C2S H2SB 108.5 . . ? C3S C2S H2SB 108.5 . . ? H2SA C2S H2SB 107.5 . . ? C2S C3S C4S 114.1(4) . . ? C2S C3S H3SA 108.7 . . ? C4S C3S H3SA 108.7 . . ? C2S C3S H3SB 108.7 . . ? C4S C3S H3SB 108.7 . . ? H3SA C3S H3SB 107.6 . . ? C1S O1S H1SC 109.5 . . ? C3S C4S H4S1 109.5 . . ? C3S C4S H4S2 109.5 . . ? H4S1 C4S H4S2 109.5 . . ? C3S C4S H4S3 109.5 . . ? H4S1 C4S H4S3 109.5 . . ? H4S2 C4S H4S3 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -2.2(6) . . . . ? N2 C1 C2 C3 175.6(4) . . . . ? C6 C1 C2 C7 176.1(4) . . . . ? N2 C1 C2 C7 -6.1(6) . . . . ? C1 C2 C3 C4 1.5(7) . . . . ? C7 C2 C3 C4 -176.8(4) . . . . ? C2 C3 C4 C5 0.6(7) . . . . ? C3 C4 C5 C6 -2.0(7) . . . . ? C4 C5 C6 C1 1.2(7) . . . . ? N2 C1 C6 C5 -176.8(4) . . . . ? C2 C1 C6 C5 0.9(7) . . . . ? C3 C2 C7 O1 -162.0(4) . . . . ? C1 C2 C7 O1 19.8(7) . . . . ? C3 C2 C7 N1 18.5(6) . . . . ? C1 C2 C7 N1 -159.8(4) . . . . ? O2 C8 N2 C1 -5.9(8) . . . . ? C9 C8 N2 C1 175.0(4) . . . . ? C6 C1 N2 C8 -14.3(7) . . . . ? C2 C1 N2 C8 167.9(4) . . . . ? C16 C11 C12 C13 -0.4(6) . . . . ? N12 C11 C12 C13 -177.9(4) . . . . ? C16 C11 C12 C17 179.7(4) . . . . ? N12 C11 C12 C17 2.2(6) . . . . ? C11 C12 C13 C14 0.7(7) . . . . ? C17 C12 C13 C14 -179.4(4) . . . . ? C12 C13 C14 C15 -0.5(7) . . . . ? C13 C14 C15 C16 -0.1(7) . . . . ? C14 C15 C16 C11 0.4(7) . . . . ? N12 C11 C16 C15 177.3(4) . . . . ? C12 C11 C16 C15 -0.1(7) . . . . ? C13 C12 C17 O11 160.8(4) . . . . ? C11 C12 C17 O11 -19.2(7) . . . . ? C13 C12 C17 N11 -18.0(6) . . . . ? C11 C12 C17 N11 162.0(4) . . . . ? O12 C18 N12 C11 -0.1(7) . . . . ? C19 C18 N12 C11 -179.2(4) . . . . ? C16 C11 N12 C18 10.1(7) . . . . ? C12 C11 N12 C18 -172.5(4) . . . . ? C26 C21 C22 C23 4.4(6) . . . . ? N22 C21 C22 C23 -177.1(4) . . . . ? C26 C21 C22 C27 -176.2(4) . . . . ? N22 C21 C22 C27 2.4(6) . . . . ? C21 C22 C23 C24 -2.2(7) . . . . ? C27 C22 C23 C24 178.3(4) . . . . ? C22 C23 C24 C25 -1.8(7) . . . . ? C23 C24 C25 C26 3.6(7) . . . . ? C24 C25 C26 C21 -1.5(7) . . . . ? N22 C21 C26 C25 178.9(4) . . . . ? C22 C21 C26 C25 -2.6(7) . . . . ? C23 C22 C27 O21 169.7(4) . . . . ? C21 C22 C27 O21 -9.8(7) . . . . ? C23 C22 C27 N21 -12.1(6) . . . . ? C21 C22 C27 N21 168.4(4) . . . . ? O22 C28 N22 C21 -0.5(8) . . . . ? C29 C28 N22 C21 177.8(4) . . . . ? C26 C21 N22 C28 -19.1(7) . . . . ? C22 C21 N22 C28 162.3(4) . . . . ? C36 C31 C32 C33 -0.8(6) . . . . ? N32 C31 C32 C33 177.9(4) . . . . ? C36 C31 C32 C37 178.5(4) . . . . ? N32 C31 C32 C37 -2.7(6) . . . . ? C31 C32 C33 C34 0.3(7) . . . . ? C37 C32 C33 C34 -179.0(4) . . . . ? C32 C33 C34 C35 0.8(7) . . . . ? C33 C34 C35 C36 -1.3(7) . . . . ? C34 C35 C36 C31 0.8(7) . . . . ? N32 C31 C36 C35 -178.5(4) . . . . ? C32 C31 C36 C35 0.3(7) . . . . ? C33 C32 C37 O31 -152.7(4) . . . . ? C31 C32 C37 O31 28.0(7) . . . . ? C33 C32 C37 N31 25.0(6) . . . . ? C31 C32 C37 N31 -154.3(4) . . . . ? O32 C38 N32 C31 -0.5(8) . . . . ? C39 C38 N32 C31 -179.0(4) . . . . ? C36 C31 N32 C38 -6.0(7) . . . . ? C32 C31 N32 C38 175.3(4) . . . . ? C46 C41 C42 C43 1.1(7) . . . . ? N42 C41 C42 C43 178.8(4) . . . . ? C46 C41 C42 C47 -178.6(4) . . . . ? N42 C41 C42 C47 -0.9(6) . . . . ? C41 C42 C43 C44 -0.4(7) . . . . ? C47 C42 C43 C44 179.3(4) . . . . ? C42 C43 C44 C45 -0.1(7) . . . . ? C43 C44 C45 C46 -0.1(7) . . . . ? C44 C45 C46 C41 0.8(8) . . . . ? C42 C41 C46 C45 -1.3(7) . . . . ? N42 C41 C46 C45 -179.0(4) . . . . ? C43 C42 C47 O41 -161.8(4) . . . . ? C41 C42 C47 O41 17.9(6) . . . . ? C43 C42 C47 N41 18.6(6) . . . . ? C41 C42 C47 N41 -161.8(4) . . . . ? O42 C48 N42 C41 -2.0(7) . . . . ? C49 C48 N42 C41 177.9(4) . . . . ? C46 C41 N42 C48 -34.8(7) . . . . ? C42 C41 N42 C48 147.6(4) . . . . ? N52 C51 C52 C53 -179.2(4) . . . . ? C56A C51 C52 C53 1.2(7) . . . . ? N52 C51 C52 C57 3.5(6) . . . . ? C56A C51 C52 C57 -176.1(4) . . . . ? C51 C52 C53 C54 -2.1(7) . . . . ? C57 C52 C53 C54 175.2(5) . . . . ? C52 C53 C54 C55 1.1(9) . . . . ? C53 C54 C55 C56A 0.8(9) . . . . ? C54 C55 C56A C51 -1.6(8) . . . . ? N52 C51 C56A C55 -179.0(5) . . . . ? C52 C51 C56A C55 0.6(7) . . . . ? C53 C52 C57 O51 160.9(4) . . . . ? C51 C52 C57 O51 -21.8(7) . . . . ? C53 C52 C57 N51 -19.0(6) . . . . ? C51 C52 C57 N51 158.3(4) . . . . ? O52 C58 N52 C51 0.1(8) . . . . ? C59 C58 N52 C51 179.1(4) . . . . ? C56A C51 N52 C58 4.0(7) . . . . ? C52 C51 N52 C58 -175.6(4) . . . . ? O1S C1S C2S C3S -57.3(7) . . . . ? C1S C2S C3S C4S -175.4(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A O31 0.88 2.02 2.881(5) 164.4 . N1 H1B O52 0.88 2.11 2.955(4) 161.0 1_445 C3 H3A O52 0.95 2.56 3.281(5) 133.0 1_445 N11 H11A O41 0.88 2.07 2.937(4) 170.7 2_666 N11 H11B O2 0.88 2.02 2.869(4) 161.4 1_556 C13 H13A O2 0.95 2.46 3.216(5) 136.2 1_556 N21 H21A O51 0.88 2.16 3.031(4) 168.8 . N21 H21B O12 0.88 2.13 2.988(5) 166.3 1_655 C23 H23A O12 0.95 2.38 3.251(5) 152.9 1_655 N31 H31A O1 0.88 2.05 2.915(5) 169.0 . N31 H31B O22 0.88 2.06 2.938(4) 171.9 . C33 H33A O22 0.95 2.43 3.174(5) 134.7 . N41 H41A O11 0.88 2.05 2.926(4) 170.6 2_666 N41 H41B O32 0.88 2.06 2.898(4) 158.1 2_656 C43 H43A O32 0.95 2.59 3.349(5) 136.7 2_656 N51 H51A O21 0.88 1.95 2.826(4) 175.1 . N51 H51B O42 0.88 3.18 3.916(5) 142.4 2_665 C53 H53A O42 0.95 2.56 3.469(5) 160.2 2_665 O1S H1SC O42 0.84 1.90 2.731(5) 168.5 1_556 C25 H25A O1S 0.95 2.66 3.459(5) 141.5 . N2 H2A O1 0.88 1.92 2.631(4) 136.4 . N12 H12A O11 0.88 1.90 2.630(4) 139.5 . N22 H22A O21 0.88 1.94 2.609(4) 131.3 . N32 H32 O31 0.88 1.95 2.663(5) 137.7 . N42 H42A O41 0.88 2.04 2.635(4) 124.2 . N52 H52A O51 0.88 1.91 2.645(4) 140.0 . _diffrn_measured_fraction_theta_max 0.856 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.942 _refine_diff_density_max 0.439 _refine_diff_density_min -0.565 _refine_diff_density_rms 0.095 data_[(AABA)6.(2-BuOH)] _database_code_depnum_ccdc_archive 'CCDC 294942' _audit_creation_method SHELXL-97 _chemical_name_systematic ; o-Acetamidobenzamide 2-Butanol solvate (6/1) ; _chemical_name_common (C9H10N2O2)6.(C4H10O) _chemical_melting_point ? _chemical_formula_moiety 'C9.67 H11.67 N2 O2.17' _chemical_formula_sum 'C9.67 H11.67 N2 O2.17' _chemical_formula_weight 190.54 _exptl_special_details ; The 2-BuOH molecule was found to be disordered with the C1S atom split over two sites; the ClSA:ClSB ratio was refined to be 70:30 and the bond lengths C2S-C1SA and C2S-C1SB restrained to be equal. The hydrogen atoms were not located for C1SA, C1SB or C2S but were included in the formula sum. ; 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' 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.8722(14) _cell_length_b 17.541(2) _cell_length_c 17.977(3) _cell_angle_alpha 73.288(3) _cell_angle_beta 86.046(3) _cell_angle_gamma 75.975(3) _cell_volume 2892.7(7) _cell_formula_units_Z 12 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3527 _cell_measurement_theta_min 2.328 _cell_measurement_theta_max 24.666 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.313 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1212 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8589 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS v2.03' _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 SMART APEX diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% None _diffrn_reflns_number 25945 _diffrn_reflns_av_R_equivalents 0.0248 _diffrn_reflns_av_sigmaI/netI 0.0595 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.25 _diffrn_reflns_theta_max 28.32 _reflns_number_total 13407 _reflns_number_gt 8363 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _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^)+(0.0759P)^2^+1.4135P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary 'direct methods' _atom_sites_solution_secondary 'difference Fourier synthesis' _atom_sites_solution_hydrogens 'Found from delta-F; OH geometrically placed' _refine_ls_hydrogen_treatment 'methyl H rigid rotor model; OH riding model; others freely refined' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 13397 _refine_ls_number_parameters 932 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1124 _refine_ls_R_factor_gt 0.0654 _refine_ls_wR_factor_ref 0.1791 _refine_ls_wR_factor_gt 0.1497 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _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 0.0262(2) 0.30426(14) 0.13804(14) 0.0267(5) Uani 1 1 d . . . C2 C 0.0170(2) 0.23164(14) 0.19627(14) 0.0266(5) Uani 1 1 d . . . C3 C -0.0602(3) 0.18160(17) 0.17941(16) 0.0369(6) Uani 1 1 d . . . H3 H -0.071(3) 0.1336(19) 0.2191(18) 0.054(9) Uiso 1 1 d . . . C4 C -0.1236(3) 0.20058(19) 0.10816(17) 0.0424(7) Uani 1 1 d . . . H4 H -0.174(3) 0.1664(19) 0.0972(18) 0.054(9) Uiso 1 1 d . . . C5 C -0.1117(3) 0.27099(18) 0.05187(17) 0.0401(7) Uani 1 1 d . . . H5 H -0.153(3) 0.2820(17) 0.0022(17) 0.045(8) Uiso 1 1 d . . . C6 C -0.0382(3) 0.32300(16) 0.06639(15) 0.0327(6) Uani 1 1 d . . . H6 H -0.035(2) 0.3726(15) 0.0277(14) 0.024(6) Uiso 1 1 d . . . C7 C 0.0911(2) 0.20665(14) 0.27241(13) 0.0263(5) Uani 1 1 d . . . O1 O 0.14928(19) 0.25342(10) 0.29208(10) 0.0339(4) Uani 1 1 d . . . N1 N 0.0973(3) 0.13158(14) 0.31940(14) 0.0335(5) Uani 1 1 d . . . H1A H 0.063(3) 0.1009(18) 0.3088(17) 0.036(8) Uiso 1 1 d . . . H1B H 0.146(3) 0.1165(18) 0.3656(18) 0.046(8) Uiso 1 1 d . . . C8 C 0.1546(3) 0.41478(15) 0.10345(15) 0.0324(6) Uani 1 1 d . . . C9 C 0.2270(3) 0.46134(17) 0.13927(16) 0.0396(6) Uani 1 1 d . . . H9A H 0.3139 0.4680 0.1112 0.059 Uiso 1 1 calc R . . H9B H 0.2483 0.4312 0.1938 0.059 Uiso 1 1 calc R . . H9C H 0.1662 0.5153 0.1363 0.059 Uiso 1 1 calc R . . O2 O 0.1468(2) 0.42957(14) 0.03315(11) 0.0550(6) Uani 1 1 d . . . N2 N 0.0992(2) 0.35720(12) 0.15429(13) 0.0295(5) Uani 1 1 d . . . H2 H 0.122(3) 0.3440(16) 0.2013(16) 0.028(7) Uiso 1 1 d . . . C11 C 0.0938(2) 0.49731(14) 0.74442(13) 0.0254(5) Uani 1 1 d . . . C12 C 0.1700(2) 0.47516(14) 0.81407(14) 0.0259(5) Uani 1 1 d . . . C13 C 0.1670(3) 0.40052(15) 0.86872(14) 0.0308(6) Uani 1 1 d . . . H13 H 0.223(2) 0.3835(14) 0.9175(14) 0.024(6) Uiso 1 1 d . . . C14 C 0.0903(3) 0.34913(16) 0.85615(15) 0.0339(6) Uani 1 1 d . . . H14 H 0.091(3) 0.2993(16) 0.8930(15) 0.028(7) Uiso 1 1 d . . . C15 C 0.0153(3) 0.37212(16) 0.78805(15) 0.0354(6) Uani 1 1 d . . . H15 H -0.041(3) 0.3381(17) 0.7798(15) 0.039(8) Uiso 1 1 d . . . C16 C 0.0168(3) 0.44495(16) 0.73262(15) 0.0329(6) Uani 1 1 d . . . H16 H -0.036(3) 0.4582(16) 0.6892(16) 0.036(7) Uiso 1 1 d . . . C17 C 0.2549(3) 0.52881(14) 0.83017(14) 0.0280(5) Uani 1 1 d . . . O11 O 0.29752(19) 0.58050(11) 0.77650(10) 0.0346(4) Uani 1 1 d . . . N11 N 0.2860(3) 0.51782(14) 0.90407(13) 0.0342(5) Uani 1 1 d . . . H11A H 0.243(3) 0.4895(18) 0.9440(17) 0.043(8) Uiso 1 1 d . . . H11B H 0.343(3) 0.550(2) 0.9159(18) 0.056(9) Uiso 1 1 d . . . C18 C 0.0203(3) 0.61200(15) 0.62439(14) 0.0290(5) Uani 1 1 d . . . C19 C 0.0548(3) 0.69035(15) 0.57775(14) 0.0336(6) Uani 1 1 d . . . H19A H -0.0220 0.7365 0.5815 0.050 Uiso 1 1 calc R . . H19B H 0.0683 0.6901 0.5233 0.050 Uiso 1 1 calc R . . H19C H 0.1406 0.6959 0.5979 0.050 Uiso 1 1 calc R . . O12 O -0.0740(2) 0.58688(11) 0.60490(10) 0.0401(5) Uani 1 1 d . . . N12 N 0.0987(2) 0.57210(12) 0.68923(11) 0.0279(5) Uani 1 1 d . . . H12 H 0.161(3) 0.5955(16) 0.6999(15) 0.031(7) Uiso 1 1 d . . . C21 C 0.6470(2) 0.41529(14) 0.49326(14) 0.0271(5) Uani 1 1 d . . . C22 C 0.7391(3) 0.46488(14) 0.49659(14) 0.0271(5) Uani 1 1 d . . . C23 C 0.8383(3) 0.43554(15) 0.55653(15) 0.0315(6) Uani 1 1 d . . . H23 H 0.906(3) 0.4674(17) 0.5549(16) 0.043(8) Uiso 1 1 d . . . C24 C 0.8442(3) 0.36198(16) 0.61297(15) 0.0370(6) Uani 1 1 d . . . H24 H 0.914(3) 0.3445(16) 0.6513(16) 0.037(7) Uiso 1 1 d . . . C25 C 0.7456(3) 0.31810(17) 0.61264(15) 0.0380(6) Uani 1 1 d . . . H25 H 0.744(3) 0.2680(17) 0.6555(16) 0.040(8) Uiso 1 1 d . . . C26 C 0.6481(3) 0.34393(16) 0.55325(15) 0.0344(6) Uani 1 1 d . . . H26 H 0.576(3) 0.3127(17) 0.5509(15) 0.040(8) Uiso 1 1 d . . . C27 C 0.7326(2) 0.54639(14) 0.43933(14) 0.0272(5) Uani 1 1 d . . . O21 O 0.67006(18) 0.56681(10) 0.37609(10) 0.0332(4) Uani 1 1 d . . . N21 N 0.7967(3) 0.59733(14) 0.45785(15) 0.0369(5) Uani 1 1 d . . . H21A H 0.802(3) 0.646(2) 0.4232(18) 0.047(9) Uiso 1 1 d . . . H21B H 0.838(3) 0.5917(18) 0.5030(19) 0.048(9) Uiso 1 1 d . . . C28 C 0.4879(3) 0.39328(15) 0.40460(15) 0.0305(6) Uani 1 1 d . . . C29 C 0.4023(3) 0.43754(17) 0.33215(15) 0.0385(6) Uani 1 1 d . . . H29A H 0.4554 0.4259 0.2870 0.058 Uiso 1 1 calc R . . H29B H 0.3802 0.4966 0.3260 0.058 Uiso 1 1 calc R . . H29C H 0.3154 0.4189 0.3363 0.058 Uiso 1 1 calc R . . O22 O 0.4953(2) 0.32094(11) 0.43683(11) 0.0463(5) Uani 1 1 d . . . N22 N 0.5564(2) 0.43966(13) 0.42974(13) 0.0306(5) Uani 1 1 d . . . H22 H 0.563(3) 0.4889(18) 0.3977(16) 0.041(8) Uiso 1 1 d . . . C31 C 0.4357(3) 0.01899(15) 0.60136(14) 0.0274(5) Uani 1 1 d . . . C32 C 0.4148(2) 0.09990(15) 0.55305(13) 0.0265(5) Uani 1 1 d . . . C33 C 0.4836(3) 0.15257(16) 0.57236(15) 0.0333(6) Uani 1 1 d . . . H33 H 0.464(3) 0.2078(18) 0.5420(16) 0.042(8) Uiso 1 1 d . . . C34 C 0.5728(3) 0.12691(17) 0.63472(15) 0.0353(6) Uani 1 1 d . . . H34 H 0.617(3) 0.1622(16) 0.6488(15) 0.034(7) Uiso 1 1 d . . . C35 C 0.5963(3) 0.04678(17) 0.67977(16) 0.0367(6) Uani 1 1 d . . . H35 H 0.661(3) 0.0271(19) 0.7247(19) 0.061(10) Uiso 1 1 d . . . C36 C 0.5289(3) -0.00701(17) 0.66355(15) 0.0347(6) Uani 1 1 d . . . H36 H 0.539(3) -0.0619(18) 0.6951(16) 0.039(8) Uiso 1 1 d . . . C37 C 0.3234(3) 0.13047(15) 0.48200(14) 0.0280(5) Uani 1 1 d . . . O31 O 0.24653(19) 0.08895(11) 0.46842(10) 0.0360(4) Uani 1 1 d . . . N31 N 0.3268(3) 0.20283(14) 0.43278(14) 0.0371(6) Uani 1 1 d . . . H31A H 0.385(3) 0.235(2) 0.4380(19) 0.058(10) Uiso 1 1 d . . . H31B H 0.276(3) 0.2169(19) 0.3901(19) 0.054(9) Uiso 1 1 d . . . C38 C 0.3506(3) -0.10916(15) 0.62852(15) 0.0326(6) Uani 1 1 d . . . C39 C 0.2602(3) -0.14725(17) 0.59359(17) 0.0410(7) Uani 1 1 d . . . H39A H 0.3168 -0.1972 0.5829 0.061 Uiso 1 1 calc R . . H39B H 0.2193 -0.1085 0.5450 0.061 Uiso 1 1 calc R . . H39C H 0.1854 -0.1610 0.6300 0.061 Uiso 1 1 calc R . . O32 O 0.4069(2) -0.14467(11) 0.69191(11) 0.0443(5) Uani 1 1 d . . . N32 N 0.3634(2) -0.03438(13) 0.58515(13) 0.0318(5) Uani 1 1 d . . . H32 H 0.314(3) -0.0120(16) 0.5454(16) 0.030(7) Uiso 1 1 d . . . C41 C 0.4481(2) 0.25730(14) 0.01868(14) 0.0277(5) Uani 1 1 d . . . C42 C 0.4605(2) 0.25786(14) 0.09610(14) 0.0267(5) Uani 1 1 d . . . C43 C 0.4000(3) 0.20476(15) 0.15454(15) 0.0295(5) Uani 1 1 d . . . H43 H 0.405(3) 0.2049(15) 0.2045(16) 0.030(7) Uiso 1 1 d . . . C44 C 0.3307(3) 0.15179(16) 0.13801(16) 0.0314(6) Uani 1 1 d . . . H44 H 0.290(3) 0.1140(16) 0.1780(15) 0.029(7) Uiso 1 1 d . . . C45 C 0.3189(3) 0.15248(16) 0.06180(16) 0.0339(6) Uani 1 1 d . . . H45 H 0.268(3) 0.1201(18) 0.0477(17) 0.050(9) Uiso 1 1 d . . . C46 C 0.3769(3) 0.20413(16) 0.00271(16) 0.0331(6) Uani 1 1 d . . . H46 H 0.364(3) 0.2060(15) -0.0481(15) 0.031(7) Uiso 1 1 d . . . C47 C 0.5308(3) 0.31621(15) 0.11608(14) 0.0286(5) Uani 1 1 d . . . O41 O 0.54378(19) 0.38031(10) 0.06620(10) 0.0345(4) Uani 1 1 d . . . N41 N 0.5752(2) 0.29871(14) 0.18846(13) 0.0337(5) Uani 1 1 d . . . H41A H 0.576(4) 0.248(2) 0.227(2) 0.068(11) Uiso 1 1 d . . . H41B H 0.621(3) 0.3351(19) 0.2018(17) 0.050(9) Uiso 1 1 d . . . C48 C 0.5367(3) 0.30958(16) -0.11433(15) 0.0323(6) Uani 1 1 d . . . C49 C 0.5891(4) 0.38099(18) -0.16543(17) 0.0480(8) Uani 1 1 d . . . H49A H 0.6882 0.3627 -0.1769 0.072 Uiso 1 1 calc R . . H49B H 0.5774 0.4235 -0.1386 0.072 Uiso 1 1 calc R . . H49C H 0.5358 0.4032 -0.2140 0.072 Uiso 1 1 calc R . . O42 O 0.52635(19) 0.25305(11) -0.13953(10) 0.0361(4) Uani 1 1 d . . . N42 N 0.5046(2) 0.31306(13) -0.04128(12) 0.0321(5) Uani 1 1 d . . . H42 H 0.517(3) 0.3585(19) -0.0252(17) 0.054(9) Uiso 1 1 d . . . C51 C 0.7785(2) 0.91977(14) 0.25002(14) 0.0274(5) Uani 1 1 d . . . C52 C 0.7119(2) 0.86301(14) 0.23465(14) 0.0270(5) Uani 1 1 d . . . C53 C 0.6245(3) 0.88957(16) 0.17017(16) 0.0330(6) Uani 1 1 d . . . H53 H 0.578(3) 0.8534(17) 0.1587(15) 0.035(7) Uiso 1 1 d . . . C54 C 0.6013(3) 0.96831(16) 0.12212(16) 0.0359(6) Uani 1 1 d . . . H54 H 0.543(3) 0.9827(18) 0.0767(18) 0.053(9) Uiso 1 1 d . . . C55 C 0.6643(3) 1.02335(16) 0.13882(16) 0.0361(6) Uani 1 1 d . . . H55 H 0.647(3) 1.0791(18) 0.1073(16) 0.042(8) Uiso 1 1 d . . . C56 C 0.7515(3) 0.99984(16) 0.20198(16) 0.0340(6) Uani 1 1 d . . . H56 H 0.792(3) 1.0343(17) 0.2147(16) 0.040(8) Uiso 1 1 d . . . C57 C 0.7305(3) 0.77701(15) 0.28648(15) 0.0300(5) Uani 1 1 d . . . O51 O 0.8143(2) 0.74997(10) 0.34203(11) 0.0405(5) Uani 1 1 d . . . N51 N 0.6538(3) 0.72989(14) 0.27246(15) 0.0356(5) Uani 1 1 d . . . H51A H 0.657(3) 0.6817(19) 0.3040(17) 0.039(8) Uiso 1 1 d . . . H51B H 0.595(3) 0.7480(18) 0.2296(18) 0.049(9) Uiso 1 1 d . . . C58 C 0.9472(3) 0.93508(16) 0.33927(15) 0.0336(6) Uani 1 1 d . . . O52 O 0.9504(2) 1.00643(12) 0.30793(13) 0.0541(6) Uani 1 1 d . . . C59 C 1.0327(3) 0.88673(16) 0.41084(16) 0.0379(6) Uani 1 1 d . . . H59A H 1.1242 0.9002 0.4057 0.057 Uiso 1 1 calc R . . H59B H 1.0451 0.8281 0.4169 0.057 Uiso 1 1 calc R . . H59C H 0.9844 0.9004 0.4565 0.057 Uiso 1 1 calc R . . N52 N 0.8692(2) 0.89383(13) 0.31454(13) 0.0309(5) Uani 1 1 d . . . H52 H 0.877(3) 0.8424(19) 0.3423(17) 0.043(8) Uiso 1 1 d . . . C1SA C 0.7659(7) 0.0612(4) 0.8971(4) 0.086(2) Uani 0.71 1 d PD A 1 C1SB C 0.8658(12) 0.0281(5) 0.8495(7) 0.052(3) Uani 0.29 1 d PD A 2 C2S C 0.8386(5) 0.1131(2) 0.8417(2) 0.0809(13) Uani 1 1 d D . . O1S O 0.7481(3) 0.16544(16) 0.78170(14) 0.0698(7) Uani 1 1 d . A . H1SA H 0.6802 0.1932 0.8005 0.105 Uiso 1 1 calc R . . C3S C 0.9097(5) 0.1632(2) 0.8746(3) 0.0917(15) Uani 1 1 d . A . H3SA H 0.9555 0.1972 0.8313 0.110 Uiso 1 1 calc R . . H3SB H 0.8369 0.2011 0.8959 0.110 Uiso 1 1 calc R . . C4S C 1.0135(4) 0.1185(3) 0.9349(3) 0.0771(12) Uani 1 1 d . . . H4S1 H 0.9687 0.0878 0.9801 0.116 Uiso 1 1 calc R A . H4S2 H 1.0552 0.1571 0.9501 0.116 Uiso 1 1 calc R . . H4S3 H 1.0864 0.0804 0.9151 0.116 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 0.0287(12) 0.0253(12) 0.0273(12) -0.0079(10) 0.0001(10) -0.0077(10) C2 0.0281(12) 0.0259(12) 0.0267(12) -0.0073(10) 0.0004(10) -0.0078(10) C3 0.0413(16) 0.0349(15) 0.0363(15) -0.0032(12) -0.0049(12) -0.0194(13) C4 0.0461(17) 0.0455(17) 0.0425(17) -0.0087(14) -0.0089(13) -0.0252(14) C5 0.0398(16) 0.0478(17) 0.0335(15) -0.0057(13) -0.0092(12) -0.0156(13) C6 0.0376(15) 0.0286(14) 0.0294(13) -0.0022(11) -0.0044(11) -0.0090(11) C7 0.0304(13) 0.0249(12) 0.0239(12) -0.0055(10) 0.0032(10) -0.0093(10) O1 0.0495(11) 0.0291(9) 0.0267(9) -0.0042(7) -0.0051(8) -0.0186(8) N1 0.0444(14) 0.0280(12) 0.0304(12) -0.0022(10) -0.0082(10) -0.0179(11) C8 0.0393(15) 0.0263(13) 0.0302(14) -0.0037(11) -0.0007(11) -0.0095(11) C9 0.0506(17) 0.0315(14) 0.0415(16) -0.0092(12) -0.0006(13) -0.0195(13) O2 0.0822(16) 0.0642(14) 0.0288(11) -0.0021(10) -0.0012(10) -0.0488(13) N2 0.0422(13) 0.0242(11) 0.0227(11) -0.0037(9) -0.0033(9) -0.0114(9) C11 0.0305(13) 0.0230(12) 0.0246(12) -0.0060(10) 0.0005(9) -0.0108(10) C12 0.0297(13) 0.0245(12) 0.0268(12) -0.0096(10) -0.0003(10) -0.0095(10) C13 0.0398(15) 0.0265(13) 0.0259(13) -0.0030(10) -0.0037(11) -0.0116(11) C14 0.0494(16) 0.0240(13) 0.0296(14) -0.0029(11) -0.0009(12) -0.0161(12) C15 0.0477(16) 0.0314(14) 0.0347(14) -0.0095(11) -0.0009(12) -0.0230(13) C16 0.0408(15) 0.0323(14) 0.0298(14) -0.0090(11) -0.0045(12) -0.0147(12) C17 0.0322(13) 0.0256(12) 0.0274(13) -0.0070(10) -0.0028(10) -0.0089(10) O11 0.0450(11) 0.0373(10) 0.0268(9) -0.0034(8) -0.0033(8) -0.0251(9) N11 0.0499(14) 0.0324(12) 0.0257(12) -0.0040(10) -0.0051(10) -0.0230(11) C18 0.0354(14) 0.0281(13) 0.0262(12) -0.0094(10) -0.0013(10) -0.0097(11) C19 0.0444(15) 0.0275(13) 0.0281(13) -0.0028(11) -0.0024(11) -0.0125(12) O12 0.0475(11) 0.0393(11) 0.0361(10) -0.0038(8) -0.0119(9) -0.0198(9) N12 0.0368(12) 0.0263(11) 0.0241(10) -0.0046(9) -0.0040(9) -0.0156(9) C21 0.0304(13) 0.0246(12) 0.0286(13) -0.0093(10) 0.0011(10) -0.0089(10) C22 0.0311(13) 0.0243(12) 0.0273(12) -0.0081(10) -0.0008(10) -0.0076(10) C23 0.0408(15) 0.0264(13) 0.0323(14) -0.0108(11) -0.0048(11) -0.0126(11) C24 0.0526(17) 0.0315(14) 0.0293(14) -0.0077(11) -0.0122(13) -0.0116(13) C25 0.0605(19) 0.0294(14) 0.0256(13) -0.0033(11) -0.0015(12) -0.0179(13) C26 0.0447(16) 0.0302(14) 0.0317(14) -0.0069(11) -0.0024(12) -0.0168(12) C27 0.0277(13) 0.0240(12) 0.0313(13) -0.0084(10) 0.0016(10) -0.0086(10) O21 0.0397(10) 0.0272(9) 0.0341(10) -0.0026(8) -0.0093(8) -0.0149(8) N21 0.0479(14) 0.0287(12) 0.0371(13) -0.0019(10) -0.0115(11) -0.0200(11) C28 0.0284(13) 0.0315(14) 0.0330(13) -0.0052(11) 0.0006(10) -0.0144(11) C29 0.0388(15) 0.0405(15) 0.0374(15) -0.0042(12) -0.0086(12) -0.0172(13) O22 0.0658(14) 0.0326(10) 0.0448(12) 0.0007(9) -0.0164(10) -0.0285(10) N22 0.0337(12) 0.0247(11) 0.0335(12) -0.0017(9) -0.0054(9) -0.0132(9) C31 0.0308(13) 0.0285(13) 0.0257(12) -0.0077(10) 0.0018(10) -0.0121(10) C32 0.0299(13) 0.0288(13) 0.0229(12) -0.0055(10) 0.0010(10) -0.0130(10) C33 0.0439(15) 0.0286(14) 0.0277(13) 0.0003(11) -0.0029(11) -0.0177(12) C34 0.0448(16) 0.0363(15) 0.0311(14) -0.0072(12) -0.0039(12) -0.0227(13) C35 0.0397(15) 0.0417(16) 0.0299(14) -0.0050(12) -0.0074(12) -0.0155(12) C36 0.0443(16) 0.0294(14) 0.0297(14) -0.0004(11) -0.0065(11) -0.0149(12) C37 0.0297(13) 0.0280(13) 0.0269(12) -0.0052(10) -0.0008(10) -0.0106(10) O31 0.0455(11) 0.0336(10) 0.0310(10) -0.0004(8) -0.0094(8) -0.0211(9) N31 0.0473(14) 0.0307(12) 0.0330(13) 0.0030(10) -0.0113(11) -0.0199(11) C38 0.0397(15) 0.0292(13) 0.0294(13) -0.0051(11) -0.0012(11) -0.0123(11) C39 0.0540(18) 0.0315(14) 0.0421(16) -0.0086(12) -0.0049(13) -0.0193(13) O32 0.0642(13) 0.0316(10) 0.0362(11) 0.0036(8) -0.0127(9) -0.0222(10) N32 0.0414(13) 0.0279(11) 0.0262(11) -0.0015(9) -0.0071(10) -0.0134(10) C41 0.0296(13) 0.0237(12) 0.0287(13) -0.0023(10) -0.0044(10) -0.0091(10) C42 0.0277(12) 0.0206(11) 0.0307(13) -0.0049(10) -0.0055(10) -0.0052(10) C43 0.0304(13) 0.0283(13) 0.0282(13) -0.0041(11) -0.0040(10) -0.0072(10) C44 0.0280(13) 0.0273(13) 0.0364(14) -0.0024(11) -0.0016(11) -0.0094(11) C45 0.0306(14) 0.0285(13) 0.0440(16) -0.0075(12) -0.0077(11) -0.0106(11) C46 0.0395(15) 0.0320(14) 0.0317(14) -0.0065(11) -0.0089(11) -0.0159(12) C47 0.0313(13) 0.0254(12) 0.0305(13) -0.0073(10) -0.0029(10) -0.0090(10) O41 0.0483(11) 0.0273(9) 0.0308(10) -0.0033(8) -0.0070(8) -0.0181(8) N41 0.0472(14) 0.0290(12) 0.0275(12) -0.0031(10) -0.0080(10) -0.0173(10) C48 0.0359(14) 0.0323(14) 0.0292(13) -0.0049(11) -0.0092(11) -0.0106(11) C49 0.068(2) 0.0423(17) 0.0368(16) -0.0048(13) 0.0051(14) -0.0277(16) O42 0.0426(11) 0.0382(10) 0.0335(10) -0.0127(8) -0.0046(8) -0.0163(9) N42 0.0438(13) 0.0281(11) 0.0292(11) -0.0045(9) -0.0055(9) -0.0198(10) C51 0.0278(12) 0.0226(12) 0.0315(13) -0.0057(10) -0.0032(10) -0.0068(10) C52 0.0278(12) 0.0210(12) 0.0322(13) -0.0068(10) -0.0022(10) -0.0060(10) C53 0.0353(14) 0.0280(13) 0.0380(15) -0.0080(11) -0.0066(11) -0.0113(11) C54 0.0397(15) 0.0306(14) 0.0359(15) -0.0026(12) -0.0121(12) -0.0102(12) C55 0.0367(15) 0.0246(13) 0.0422(16) 0.0015(12) -0.0074(12) -0.0091(11) C56 0.0374(15) 0.0225(13) 0.0432(16) -0.0047(11) -0.0081(12) -0.0122(11) C57 0.0315(13) 0.0236(12) 0.0355(14) -0.0066(11) -0.0049(11) -0.0083(10) O51 0.0485(11) 0.0254(9) 0.0474(11) 0.0007(8) -0.0213(9) -0.0152(8) N51 0.0463(14) 0.0227(11) 0.0402(13) -0.0024(10) -0.0131(11) -0.0165(10) C58 0.0370(14) 0.0295(14) 0.0367(14) -0.0071(11) -0.0064(11) -0.0134(11) O52 0.0729(15) 0.0320(11) 0.0604(14) 0.0045(10) -0.0299(11) -0.0304(10) C59 0.0425(16) 0.0361(15) 0.0364(15) -0.0051(12) -0.0113(12) -0.0143(12) N52 0.0373(12) 0.0222(11) 0.0339(12) -0.0015(9) -0.0085(9) -0.0134(9) C1SA 0.096(5) 0.063(4) 0.093(4) 0.023(3) -0.047(4) -0.047(4) C1SB 0.057(7) 0.039(6) 0.066(8) -0.019(5) -0.025(6) -0.015(5) C2S 0.103(3) 0.058(2) 0.078(3) -0.016(2) -0.051(3) -0.002(2) O1S 0.0712(17) 0.0724(17) 0.0557(15) -0.0117(13) -0.0108(12) -0.0021(13) C3S 0.088(3) 0.051(2) 0.135(4) -0.015(3) -0.042(3) -0.015(2) C4S 0.067(3) 0.077(3) 0.099(3) -0.038(2) -0.004(2) -0.021(2) _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 C6 1.393(3) . ? C1 N2 1.406(3) . ? C1 C2 1.415(3) . ? C2 C3 1.397(3) . ? C2 C7 1.497(3) . ? C3 C4 1.382(4) . ? C3 H3 0.96(3) . ? C4 C5 1.378(4) . ? C4 H4 0.93(3) . ? C5 C6 1.382(4) . ? C5 H5 0.95(3) . ? C6 H6 0.95(2) . ? C7 O1 1.245(3) . ? C7 N1 1.334(3) . ? N1 H1A 0.77(3) . ? N1 H1B 0.93(3) . ? C8 O2 1.219(3) . ? C8 N2 1.350(3) . ? C8 C9 1.497(4) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? N2 H2 0.84(3) . ? C11 C16 1.392(3) . ? C11 N12 1.408(3) . ? C11 C12 1.412(3) . ? C12 C13 1.398(3) . ? C12 C17 1.498(3) . ? C13 C14 1.382(4) . ? C13 H13 1.00(2) . ? C14 C15 1.380(4) . ? C14 H14 0.93(3) . ? C15 C16 1.379(4) . ? C15 H15 0.95(3) . ? C16 H16 0.91(3) . ? C17 O11 1.247(3) . ? C17 N11 1.333(3) . ? N11 H11A 0.89(3) . ? N11 H11B 0.96(3) . ? C18 O12 1.231(3) . ? C18 N12 1.357(3) . ? C18 C19 1.494(3) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? N12 H12 0.87(3) . ? C21 C26 1.396(3) . ? C21 N22 1.401(3) . ? C21 C22 1.417(3) . ? C22 C23 1.403(3) . ? C22 C27 1.492(3) . ? C23 C24 1.384(4) . ? C23 H23 0.97(3) . ? C24 C25 1.380(4) . ? C24 H24 0.94(3) . ? C25 C26 1.387(4) . ? C25 H25 0.99(3) . ? C26 H26 1.01(3) . ? C27 O21 1.248(3) . ? C27 N21 1.336(3) . ? N21 H21A 0.91(3) . ? N21 H21B 0.90(3) . ? C28 O22 1.220(3) . ? C28 N22 1.358(3) . ? C28 C29 1.505(3) . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? N22 H22 0.90(3) . ? C31 C36 1.397(3) . ? C31 N32 1.407(3) . ? C31 C32 1.409(3) . ? C32 C33 1.399(3) . ? C32 C37 1.504(3) . ? C33 C34 1.375(4) . ? C33 H33 0.95(3) . ? C34 C35 1.378(4) . ? C34 H34 0.93(3) . ? C35 C36 1.381(4) . ? C35 H35 0.99(3) . ? C36 H36 0.95(3) . ? C37 O31 1.250(3) . ? C37 N31 1.329(3) . ? N31 H31A 0.92(3) . ? N31 H31B 0.89(3) . ? C38 O32 1.228(3) . ? C38 N32 1.350(3) . ? C38 C39 1.498(4) . ? C39 H39A 0.9800 . ? C39 H39B 0.9800 . ? C39 H39C 0.9800 . ? N32 H32 0.83(3) . ? C41 C46 1.395(3) . ? C41 C42 1.408(3) . ? C41 N42 1.416(3) . ? C42 C43 1.396(3) . ? C42 C47 1.500(3) . ? C43 C44 1.383(4) . ? C43 H43 0.90(3) . ? C44 C45 1.379(4) . ? C44 H44 0.97(3) . ? C45 C46 1.375(4) . ? C45 H45 0.94(3) . ? C46 H46 0.92(3) . ? C47 O41 1.249(3) . ? C47 N41 1.328(3) . ? N41 H41A 0.95(4) . ? N41 H41B 0.95(3) . ? C48 O42 1.230(3) . ? C48 N42 1.345(3) . ? C48 C49 1.506(4) . ? C49 H49A 0.9800 . ? C49 H49B 0.9800 . ? C49 H49C 0.9800 . ? N42 H42 0.96(3) . ? C51 C56 1.394(3) . ? C51 N52 1.413(3) . ? C51 C52 1.414(3) . ? C52 C53 1.392(3) . ? C52 C57 1.503(3) . ? C53 C54 1.376(4) . ? C53 H53 0.94(3) . ? C54 C55 1.376(4) . ? C54 H54 0.97(3) . ? C55 C56 1.376(4) . ? C55 H55 0.96(3) . ? C56 H56 0.89(3) . ? C57 O51 1.248(3) . ? C57 N51 1.331(3) . ? N51 H51A 0.87(3) . ? N51 H51B 0.93(3) . ? C58 O52 1.223(3) . ? C58 N52 1.348(3) . ? C58 C59 1.504(3) . ? C59 H59A 0.9800 . ? C59 H59B 0.9800 . ? C59 H59C 0.9800 . ? N52 H52 0.88(3) . ? C1SA C2S 1.425(6) . ? C1SB C2S 1.416(8) . ? C2S O1S 1.404(4) . ? C2S C3S 1.508(5) . ? O1S H1SA 0.8400 . ? C3S C4S 1.454(5) . ? C3S H3SA 0.9900 . ? C3S H3SB 0.9900 . ? C4S H4S1 0.9800 . ? C4S H4S2 0.9800 . ? C4S H4S3 0.9800 . ? 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 C1 N2 121.0(2) . . ? C6 C1 C2 120.0(2) . . ? N2 C1 C2 119.0(2) . . ? C3 C2 C1 117.7(2) . . ? C3 C2 C7 120.4(2) . . ? C1 C2 C7 121.9(2) . . ? C4 C3 C2 121.9(3) . . ? C4 C3 H3 119.3(19) . . ? C2 C3 H3 118.8(19) . . ? C5 C4 C3 119.5(3) . . ? C5 C4 H4 119.2(19) . . ? C3 C4 H4 121.3(19) . . ? C4 C5 C6 120.6(3) . . ? C4 C5 H5 118.4(18) . . ? C6 C5 H5 121.0(18) . . ? C5 C6 C1 120.3(2) . . ? C5 C6 H6 119.3(15) . . ? C1 C6 H6 120.4(15) . . ? O1 C7 N1 119.5(2) . . ? O1 C7 C2 121.7(2) . . ? N1 C7 C2 118.8(2) . . ? C7 N1 H1A 122(2) . . ? C7 N1 H1B 117.7(18) . . ? H1A N1 H1B 120(3) . . ? O2 C8 N2 123.7(2) . . ? O2 C8 C9 121.1(2) . . ? N2 C8 C9 115.3(2) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 N2 C1 128.1(2) . . ? C8 N2 H2 118.1(18) . . ? C1 N2 H2 112.7(18) . . ? C16 C11 N12 122.4(2) . . ? C16 C11 C12 119.2(2) . . ? N12 C11 C12 118.4(2) . . ? C13 C12 C11 118.7(2) . . ? C13 C12 C17 119.5(2) . . ? C11 C12 C17 121.8(2) . . ? C14 C13 C12 121.4(2) . . ? C14 C13 H13 119.3(14) . . ? C12 C13 H13 119.3(14) . . ? C15 C14 C13 119.1(2) . . ? C15 C14 H14 120.8(16) . . ? C13 C14 H14 120.1(16) . . ? C16 C15 C14 121.0(2) . . ? C16 C15 H15 119.2(16) . . ? C14 C15 H15 119.7(16) . . ? C15 C16 C11 120.5(2) . . ? C15 C16 H16 117.9(17) . . ? C11 C16 H16 121.6(17) . . ? O11 C17 N11 121.2(2) . . ? O11 C17 C12 121.4(2) . . ? N11 C17 C12 117.4(2) . . ? C17 N11 H11A 123.0(19) . . ? C17 N11 H11B 119.2(19) . . ? H11A N11 H11B 117(3) . . ? O12 C18 N12 123.3(2) . . ? O12 C18 C19 121.5(2) . . ? N12 C18 C19 115.2(2) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C18 N12 C11 129.2(2) . . ? C18 N12 H12 117.1(17) . . ? C11 N12 H12 113.6(17) . . ? C26 C21 N22 121.7(2) . . ? C26 C21 C22 119.4(2) . . ? N22 C21 C22 118.9(2) . . ? C23 C22 C21 118.0(2) . . ? C23 C22 C27 119.8(2) . . ? C21 C22 C27 122.2(2) . . ? C24 C23 C22 121.8(2) . . ? C24 C23 H23 121.1(17) . . ? C22 C23 H23 116.9(17) . . ? C25 C24 C23 119.2(3) . . ? C25 C24 H24 122.4(17) . . ? C23 C24 H24 118.4(17) . . ? C24 C25 C26 120.6(2) . . ? C24 C25 H25 119.7(16) . . ? C26 C25 H25 119.7(16) . . ? C25 C26 C21 120.5(2) . . ? C25 C26 H26 122.5(16) . . ? C21 C26 H26 117.0(16) . . ? O21 C27 N21 120.6(2) . . ? O21 C27 C22 121.7(2) . . ? N21 C27 C22 117.7(2) . . ? C27 N21 H21A 120.6(19) . . ? C27 N21 H21B 128.9(19) . . ? H21A N21 H21B 110(3) . . ? O22 C28 N22 123.5(2) . . ? O22 C28 C29 121.6(2) . . ? N22 C28 C29 114.8(2) . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C28 N22 C21 128.0(2) . . ? C28 N22 H22 119.1(18) . . ? C21 N22 H22 111.3(18) . . ? C36 C31 N32 121.3(2) . . ? C36 C31 C32 119.5(2) . . ? N32 C31 C32 119.1(2) . . ? C33 C32 C31 117.9(2) . . ? C33 C32 C37 119.7(2) . . ? C31 C32 C37 122.4(2) . . ? C34 C33 C32 122.1(2) . . ? C34 C33 H33 120.5(17) . . ? C32 C33 H33 117.4(17) . . ? C33 C34 C35 119.4(3) . . ? C33 C34 H34 122.5(16) . . ? C35 C34 H34 118.1(16) . . ? C34 C35 C36 120.5(2) . . ? C34 C35 H35 120.3(19) . . ? C36 C35 H35 119.2(19) . . ? C35 C36 C31 120.5(2) . . ? C35 C36 H36 122.5(17) . . ? C31 C36 H36 116.9(17) . . ? O31 C37 N31 120.0(2) . . ? O31 C37 C32 121.4(2) . . ? N31 C37 C32 118.6(2) . . ? C37 N31 H31A 124(2) . . ? C37 N31 H31B 116(2) . . ? H31A N31 H31B 120(3) . . ? O32 C38 N32 124.0(2) . . ? O32 C38 C39 121.2(2) . . ? N32 C38 C39 114.8(2) . . ? C38 C39 H39A 109.5 . . ? C38 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? C38 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? C38 N32 C31 129.6(2) . . ? C38 N32 H32 118.1(18) . . ? C31 N32 H32 111.7(18) . . ? C46 C41 C42 119.5(2) . . ? C46 C41 N42 121.7(2) . . ? C42 C41 N42 118.7(2) . . ? C43 C42 C41 118.3(2) . . ? C43 C42 C47 120.0(2) . . ? C41 C42 C47 121.6(2) . . ? C44 C43 C42 121.6(2) . . ? C44 C43 H43 118.8(17) . . ? C42 C43 H43 119.6(17) . . ? C45 C44 C43 119.2(2) . . ? C45 C44 H44 118.3(15) . . ? C43 C44 H44 122.4(15) . . ? C46 C45 C44 120.7(2) . . ? C46 C45 H45 117.1(18) . . ? C44 C45 H45 122.1(18) . . ? C45 C46 C41 120.6(2) . . ? C45 C46 H46 119.6(16) . . ? C41 C46 H46 119.7(16) . . ? O41 C47 N41 121.3(2) . . ? O41 C47 C42 120.5(2) . . ? N41 C47 C42 118.1(2) . . ? C47 N41 H41A 124(2) . . ? C47 N41 H41B 118.9(18) . . ? H41A N41 H41B 117(3) . . ? O42 C48 N42 124.2(2) . . ? O42 C48 C49 120.7(2) . . ? N42 C48 C49 115.1(2) . . ? C48 C49 H49A 109.5 . . ? C48 C49 H49B 109.5 . . ? H49A C49 H49B 109.5 . . ? C48 C49 H49C 109.5 . . ? H49A C49 H49C 109.5 . . ? H49B C49 H49C 109.5 . . ? C48 N42 C41 128.1(2) . . ? C48 N42 H42 119.8(18) . . ? C41 N42 H42 112.0(18) . . ? C56 C51 N52 121.8(2) . . ? C56 C51 C52 119.3(2) . . ? N52 C51 C52 118.9(2) . . ? C53 C52 C51 117.9(2) . . ? C53 C52 C57 120.0(2) . . ? C51 C52 C57 122.0(2) . . ? C54 C53 C52 122.2(2) . . ? C54 C53 H53 118.0(16) . . ? C52 C53 H53 119.8(16) . . ? C55 C54 C53 119.2(2) . . ? C55 C54 H54 122.1(18) . . ? C53 C54 H54 118.6(18) . . ? C54 C55 C56 120.6(2) . . ? C54 C55 H55 120.8(17) . . ? C56 C55 H55 118.6(17) . . ? C55 C56 C51 120.8(2) . . ? C55 C56 H56 122.5(18) . . ? C51 C56 H56 116.7(18) . . ? O51 C57 N51 120.2(2) . . ? O51 C57 C52 121.5(2) . . ? N51 C57 C52 118.3(2) . . ? C57 N51 H51A 120.1(19) . . ? C57 N51 H51B 121.3(19) . . ? H51A N51 H51B 119(3) . . ? O52 C58 N52 124.4(2) . . ? O52 C58 C59 120.7(2) . . ? N52 C58 C59 114.8(2) . . ? C58 C59 H59A 109.5 . . ? C58 C59 H59B 109.5 . . ? H59A C59 H59B 109.5 . . ? C58 C59 H59C 109.5 . . ? H59A C59 H59C 109.5 . . ? H59B C59 H59C 109.5 . . ? C58 N52 C51 129.9(2) . . ? C58 N52 H52 115.3(19) . . ? C51 N52 H52 114.9(19) . . ? O1S C2S C1SB 117.1(5) . . ? O1S C2S C1SA 110.3(4) . . ? C1SB C2S C1SA 58.6(6) . . ? O1S C2S C3S 109.2(3) . . ? C1SB C2S C3S 132.4(5) . . ? C1SA C2S C3S 115.0(4) . . ? C2S O1S H1SA 109.5 . . ? C4S C3S C2S 116.8(3) . . ? C4S C3S H3SA 108.1 . . ? C2S C3S H3SA 108.1 . . ? C4S C3S H3SB 108.1 . . ? C2S C3S H3SB 108.1 . . ? H3SA C3S H3SB 107.3 . . ? C3S C4S H4S1 109.5 . . ? C3S C4S H4S2 109.5 . . ? H4S1 C4S H4S2 109.5 . . ? C3S C4S H4S3 109.5 . . ? H4S1 C4S H4S3 109.5 . . ? H4S2 C4S H4S3 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -1.1(4) . . . . ? N2 C1 C2 C3 177.9(2) . . . . ? C6 C1 C2 C7 176.5(2) . . . . ? N2 C1 C2 C7 -4.5(3) . . . . ? C1 C2 C3 C4 1.2(4) . . . . ? C7 C2 C3 C4 -176.4(3) . . . . ? C2 C3 C4 C5 -0.3(5) . . . . ? C3 C4 C5 C6 -0.7(5) . . . . ? C4 C5 C6 C1 0.8(4) . . . . ? N2 C1 C6 C5 -178.8(2) . . . . ? C2 C1 C6 C5 0.1(4) . . . . ? C3 C2 C7 O1 -172.9(2) . . . . ? C1 C2 C7 O1 9.5(4) . . . . ? C3 C2 C7 N1 8.5(4) . . . . ? C1 C2 C7 N1 -169.0(2) . . . . ? O2 C8 N2 C1 0.8(4) . . . . ? C9 C8 N2 C1 -179.8(2) . . . . ? C6 C1 N2 C8 -21.9(4) . . . . ? C2 C1 N2 C8 159.2(2) . . . . ? C16 C11 C12 C13 0.8(4) . . . . ? N12 C11 C12 C13 -179.2(2) . . . . ? C16 C11 C12 C17 179.9(2) . . . . ? N12 C11 C12 C17 -0.1(3) . . . . ? C11 C12 C13 C14 -0.8(4) . . . . ? C17 C12 C13 C14 -179.9(2) . . . . ? C12 C13 C14 C15 0.1(4) . . . . ? C13 C14 C15 C16 0.4(4) . . . . ? C14 C15 C16 C11 -0.4(4) . . . . ? N12 C11 C16 C15 179.7(2) . . . . ? C12 C11 C16 C15 -0.3(4) . . . . ? C13 C12 C17 O11 156.7(2) . . . . ? C11 C12 C17 O11 -22.4(4) . . . . ? C13 C12 C17 N11 -21.7(4) . . . . ? C11 C12 C17 N11 159.1(2) . . . . ? O12 C18 N12 C11 1.6(4) . . . . ? C19 C18 N12 C11 -179.2(2) . . . . ? C16 C11 N12 C18 10.6(4) . . . . ? C12 C11 N12 C18 -169.3(2) . . . . ? C26 C21 C22 C23 6.5(4) . . . . ? N22 C21 C22 C23 -173.9(2) . . . . ? C26 C21 C22 C27 -173.0(2) . . . . ? N22 C21 C22 C27 6.6(4) . . . . ? C21 C22 C23 C24 -2.4(4) . . . . ? C27 C22 C23 C24 177.1(2) . . . . ? C22 C23 C24 C25 -3.2(4) . . . . ? C23 C24 C25 C26 4.9(4) . . . . ? C24 C25 C26 C21 -0.8(4) . . . . ? N22 C21 C26 C25 175.4(2) . . . . ? C22 C21 C26 C25 -5.0(4) . . . . ? C23 C22 C27 O21 163.4(2) . . . . ? C21 C22 C27 O21 -17.1(4) . . . . ? C23 C22 C27 N21 -16.5(4) . . . . ? C21 C22 C27 N21 163.1(2) . . . . ? O22 C28 N22 C21 1.4(4) . . . . ? C29 C28 N22 C21 -177.7(2) . . . . ? C26 C21 N22 C28 -19.0(4) . . . . ? C22 C21 N22 C28 161.4(2) . . . . ? C36 C31 C32 C33 -3.5(4) . . . . ? N32 C31 C32 C33 177.5(2) . . . . ? C36 C31 C32 C37 175.8(2) . . . . ? N32 C31 C32 C37 -3.2(4) . . . . ? C31 C32 C33 C34 2.1(4) . . . . ? C37 C32 C33 C34 -177.2(2) . . . . ? C32 C33 C34 C35 0.3(4) . . . . ? C33 C34 C35 C36 -1.3(4) . . . . ? C34 C35 C36 C31 -0.1(4) . . . . ? N32 C31 C36 C35 -178.4(2) . . . . ? C32 C31 C36 C35 2.6(4) . . . . ? C33 C32 C37 O31 -170.7(2) . . . . ? C31 C32 C37 O31 10.0(4) . . . . ? C33 C32 C37 N31 10.1(4) . . . . ? C31 C32 C37 N31 -169.2(2) . . . . ? O32 C38 N32 C31 -2.0(5) . . . . ? C39 C38 N32 C31 177.8(3) . . . . ? C36 C31 N32 C38 11.7(4) . . . . ? C32 C31 N32 C38 -169.2(3) . . . . ? C46 C41 C42 C43 -0.2(4) . . . . ? N42 C41 C42 C43 177.7(2) . . . . ? C46 C41 C42 C47 -177.4(2) . . . . ? N42 C41 C42 C47 0.4(4) . . . . ? C41 C42 C43 C44 0.8(4) . . . . ? C47 C42 C43 C44 178.1(2) . . . . ? C42 C43 C44 C45 -1.2(4) . . . . ? C43 C44 C45 C46 1.0(4) . . . . ? C44 C45 C46 C41 -0.4(4) . . . . ? C42 C41 C46 C45 0.0(4) . . . . ? N42 C41 C46 C45 -177.8(2) . . . . ? C43 C42 C47 O41 -156.1(2) . . . . ? C41 C42 C47 O41 21.1(4) . . . . ? C43 C42 C47 N41 22.2(3) . . . . ? C41 C42 C47 N41 -160.6(2) . . . . ? O42 C48 N42 C41 -3.3(4) . . . . ? C49 C48 N42 C41 177.2(2) . . . . ? C46 C41 N42 C48 -20.9(4) . . . . ? C42 C41 N42 C48 161.3(2) . . . . ? C56 C51 C52 C53 1.8(4) . . . . ? N52 C51 C52 C53 -179.2(2) . . . . ? C56 C51 C52 C57 -176.8(2) . . . . ? N52 C51 C52 C57 2.3(4) . . . . ? C51 C52 C53 C54 -0.2(4) . . . . ? C57 C52 C53 C54 178.3(3) . . . . ? C52 C53 C54 C55 -1.2(4) . . . . ? C53 C54 C55 C56 1.1(4) . . . . ? C54 C55 C56 C51 0.4(4) . . . . ? N52 C51 C56 C55 179.1(3) . . . . ? C52 C51 C56 C55 -1.9(4) . . . . ? C53 C52 C57 O51 175.8(3) . . . . ? C51 C52 C57 O51 -5.7(4) . . . . ? C53 C52 C57 N51 -5.0(4) . . . . ? C51 C52 C57 N51 173.5(2) . . . . ? O52 C58 N52 C51 0.9(5) . . . . ? C59 C58 N52 C51 -179.6(3) . . . . ? C56 C51 N52 C58 -3.5(4) . . . . ? C52 C51 N52 C58 177.5(3) . . . . ? O1S C2S C3S C4S -176.8(4) . . . . ? C1SB C2S C3S C4S -10.8(11) . . . . ? C1SA C2S C3S C4S 58.6(6) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1B O31 0.93(3) 2.04(3) 2.961(3) 177(3) . N1 H1A O52 0.77(3) 2.21(3) 2.968(3) 166(3) 1_445 C3 H3 O52 0.96(3) 2.31(3) 3.253(3) 168(3) 1_445 N11 H11B O41 0.96(3) 1.95(3) 2.903(3) 176(3) 2_666 N11 H11A O2 0.89(3) 1.97(3) 2.863(3) 178(3) 1_556 C13 H13 O2 1.00(2) 2.45(2) 3.126(3) 124.4(17) 1_556 N21 H21A O51 0.91(3) 2.01(3) 2.916(3) 177(3) . N21 H21B O12 0.90(3) 2.05(3) 2.954(3) 176(3) 1_655 C23 H23 O12 0.97(3) 2.56(3) 3.331(3) 137(2) 1_655 N31 H31B O1 0.89(3) 2.08(3) 2.970(3) 177(3) . N31 H31A O22 0.92(3) 2.06(4) 2.973(3) 171(3) . C33 H33 O22 0.95(3) 2.38(3) 3.265(3) 155(2) . N41 H41B O11 0.95(3) 1.99(3) 2.938(3) 175(3) 2_666 N41 H41A O32 0.95(4) 1.95(4) 2.904(3) 175(3) 2_656 C43 H43 O32 0.90(3) 2.53(3) 3.232(3) 135(2) 2_656 N51 H51A O21 0.87(3) 2.04(3) 2.904(3) 178(3) . N51 H51B O42 0.93(3) 2.08(3) 2.980(3) 161(3) 2_665 C53 H53 O42 0.94(3) 2.46(3) 3.390(3) 174(2) 2_665 O1S H1SA O42 0.84 2.06 2.890(3) 172.5 1_556 C25 H25 O1S 0.99(3) 2.45(3) 3.421(4) 166(2) . N2 H2 O1 0.84(3) 1.90(3) 2.614(3) 142(2) . N12 H12 O11 0.87(3) 1.92(3) 2.652(3) 141(2) . N22 H22 O21 0.90(3) 1.86(3) 2.644(3) 143(3) . N32 H32 O31 0.83(3) 1.91(3) 2.632(3) 145(3) . N42 H42 O41 0.96(3) 1.84(3) 2.628(3) 138(3) . N52 H52 O51 0.88(3) 1.87(3) 2.610(3) 140(3) . _diffrn_measured_fraction_theta_max 0.930 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.854 _refine_diff_density_min -0.387 _refine_diff_density_rms 0.058 data_[(AABA)6.(DCE)] _database_code_depnum_ccdc_archive 'CCDC 294943' _audit_creation_method SHELXL-97 _chemical_name_systematic ; o-Acetamidobenzamide 1,2-Dichloroethane solvate (6/1) ; _chemical_name_common (C9H10N2O2)6.(C2H4Cl2) _chemical_melting_point ? _chemical_formula_moiety 'C9.33 H10.67 Cl0.33 N2 O2' _chemical_formula_sum 'C9.33 H10.67 Cl0.33 N2 O2' _chemical_formula_weight 194.68 _exptl_special_details ; The crystal used to collect data decomposed two thirds of the way through the data collection due to a fault with the kryoflex (severe icing occurred causing the crystal to decay) so, only the data collected up to this point was used for the solution and refinement. The DCE molecule was found to be partially disordered over two sites; C2S, C2T and Cl2S, Cl2T were modelled over two sites with an occupancy ratio of 75:25. The bond lengths C1S-C2S and C1S-C2T were restrained to be equal, as were the bond lengths C2S-Cl2S and C2T-Cl2T. The disordered atoms were refined isotropically. None of the DCE hydrogen atoms were located but they were included in the formula sum. ; 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' 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.2597(12) _cell_length_b 17.732(2) _cell_length_c 19.021(2) _cell_angle_alpha 71.009(2) _cell_angle_beta 87.503(3) _cell_angle_gamma 75.724(3) _cell_volume 2859.6(6) _cell_formula_units_Z 12 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2422 _cell_measurement_theta_min 2.392 _cell_measurement_theta_max 26.285 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.357 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1228 _exptl_absorpt_coefficient_mu 0.186 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.848 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'SADABS v2.03' _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 SMART APEX diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% None _diffrn_reflns_number 14461 _diffrn_reflns_av_R_equivalents 0.0327 _diffrn_reflns_av_sigmaI/netI 0.0674 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 28.30 _reflns_number_total 11640 _reflns_number_gt 7255 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _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^)+(0.0928P)^2^+2.0338P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary 'direct methods' _atom_sites_solution_secondary 'difference Fourier synthesis' _atom_sites_solution_hydrogens 'Found from delta-F' _refine_ls_hydrogen_treatment 'methyl H rigid rotor model; others freely refined' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 11633 _refine_ls_number_parameters 911 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1098 _refine_ls_R_factor_gt 0.0679 _refine_ls_wR_factor_ref 0.1986 _refine_ls_wR_factor_gt 0.1735 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _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 0.0208(3) 0.30350(16) 0.13041(15) 0.0244(6) Uani 1 1 d . . . C2 C 0.0068(3) 0.23155(17) 0.18757(15) 0.0251(6) Uani 1 1 d . . . C3 C -0.0679(3) 0.1802(2) 0.17031(17) 0.0315(7) Uani 1 1 d . . . H3 H -0.084(3) 0.135(2) 0.2066(19) 0.037(9) Uiso 1 1 d . . . C4 C -0.1229(4) 0.1965(2) 0.09931(18) 0.0363(8) Uani 1 1 d . . . H4 H -0.172(4) 0.164(2) 0.0924(19) 0.043(10) Uiso 1 1 d . . . C5 C -0.1075(3) 0.26631(19) 0.04422(18) 0.0316(7) Uani 1 1 d . . . H5 H -0.140(3) 0.2736(17) 0.0004(18) 0.025(8) Uiso 1 1 d . . . C6 C -0.0378(3) 0.32026(18) 0.05916(16) 0.0294(7) Uani 1 1 d . . . H6 H -0.028(3) 0.3700(19) 0.0196(17) 0.030(8) Uiso 1 1 d . . . C7 C 0.0757(3) 0.20801(17) 0.26349(15) 0.0257(6) Uani 1 1 d . . . O1 O 0.1254(2) 0.25719(12) 0.28393(11) 0.0334(5) Uani 1 1 d . . . N1 N 0.0870(3) 0.13180(17) 0.30935(15) 0.0345(6) Uani 1 1 d . . . H1A H 0.125(4) 0.122(2) 0.353(2) 0.038(10) Uiso 1 1 d . . . H1B H 0.052(4) 0.095(2) 0.301(2) 0.044(11) Uiso 1 1 d . . . C8 C 0.1542(3) 0.41459(17) 0.09825(16) 0.0270(6) Uani 1 1 d . . . C9 C 0.2250(3) 0.46228(18) 0.13295(17) 0.0328(7) Uani 1 1 d . . . H9A H 0.3159 0.4721 0.1071 0.049 Uiso 1 1 calc R . . H9B H 0.2503 0.4308 0.1856 0.049 Uiso 1 1 calc R . . H9C H 0.1550 0.5151 0.1288 0.049 Uiso 1 1 calc R . . O2 O 0.1542(3) 0.42765(15) 0.03132(12) 0.0467(6) Uani 1 1 d . . . N2 N 0.0923(3) 0.35741(14) 0.14626(14) 0.0266(5) Uani 1 1 d . . . H2 H 0.111(3) 0.3468(17) 0.1909(18) 0.021(8) Uiso 1 1 d . . . C11 C 0.0886(3) 0.49501(16) 0.74622(15) 0.0235(6) Uani 1 1 d . . . C12 C 0.1609(3) 0.47605(17) 0.81621(15) 0.0243(6) Uani 1 1 d . . . C13 C 0.1563(3) 0.40205(17) 0.87099(16) 0.0267(6) Uani 1 1 d . . . H13 H 0.205(3) 0.3938(18) 0.9139(18) 0.030(8) Uiso 1 1 d . . . C14 C 0.0837(3) 0.34769(18) 0.85887(17) 0.0303(7) Uani 1 1 d . . . H14 H 0.077(3) 0.2990(19) 0.8993(17) 0.031(8) Uiso 1 1 d . . . C15 C 0.0135(3) 0.36710(18) 0.79059(17) 0.0296(7) Uani 1 1 d . . . H15 H -0.043(4) 0.334(2) 0.7793(19) 0.045(10) Uiso 1 1 d . . . C16 C 0.0154(3) 0.43980(18) 0.73481(17) 0.0286(7) Uani 1 1 d . . . H16 H -0.030(3) 0.4494(18) 0.6910(18) 0.032(8) Uiso 1 1 d . . . C17 C 0.2437(3) 0.53195(17) 0.83157(16) 0.0246(6) Uani 1 1 d . . . O11 O 0.2832(2) 0.58659(13) 0.77979(11) 0.0330(5) Uani 1 1 d . . . N11 N 0.2773(3) 0.52141(16) 0.90194(14) 0.0289(6) Uani 1 1 d . . . H11A H 0.232(4) 0.491(2) 0.938(2) 0.046(10) Uiso 1 1 d . . . H11B H 0.325(4) 0.555(2) 0.909(2) 0.045(10) Uiso 1 1 d . . . C18 C 0.0210(3) 0.60537(18) 0.62305(16) 0.0276(6) Uani 1 1 d . . . C19 C 0.0567(4) 0.68482(18) 0.57817(16) 0.0319(7) Uani 1 1 d . . . H19A H 0.0496 0.6917 0.5251 0.048 Uiso 1 1 calc R . . H19B H 0.1581 0.6841 0.5916 0.048 Uiso 1 1 calc R . . H19C H -0.0143 0.7306 0.5885 0.048 Uiso 1 1 calc R . . O12 O -0.0683(2) 0.57692(13) 0.60023(11) 0.0376(5) Uani 1 1 d . . . N12 N 0.0934(3) 0.56923(15) 0.69051(13) 0.0268(5) Uani 1 1 d . . . H12 H 0.152(3) 0.5919(19) 0.7030(17) 0.027(9) Uiso 1 1 d . . . C21 C 0.6323(3) 0.41842(17) 0.48363(15) 0.0256(6) Uani 1 1 d . . . C22 C 0.7260(3) 0.46710(17) 0.49151(16) 0.0258(6) Uani 1 1 d . . . C23 C 0.8188(4) 0.43860(19) 0.55503(18) 0.0329(7) Uani 1 1 d . . . H23 H 0.882(4) 0.471(2) 0.5577(18) 0.037(9) Uiso 1 1 d . . . C24 C 0.8162(4) 0.3664(2) 0.61148(19) 0.0413(8) Uani 1 1 d . . . H24 H 0.882(4) 0.350(2) 0.650(2) 0.060(12) Uiso 1 1 d . . . C25 C 0.7150(4) 0.3230(2) 0.60493(18) 0.0415(8) Uani 1 1 d . . . H25 H 0.707(4) 0.275(2) 0.646(2) 0.044(10) Uiso 1 1 d . . . C26 C 0.6242(4) 0.34784(19) 0.54248(17) 0.0342(7) Uani 1 1 d . . . H26 H 0.557(3) 0.3189(18) 0.5372(16) 0.025(8) Uiso 1 1 d . . . C27 C 0.7290(3) 0.54726(17) 0.43351(16) 0.0260(6) Uani 1 1 d . . . O21 O 0.6722(2) 0.56658(12) 0.36977(11) 0.0320(5) Uani 1 1 d . . . N21 N 0.7930(3) 0.59816(17) 0.45147(16) 0.0340(6) Uani 1 1 d . . . H21A H 0.822(4) 0.587(2) 0.497(2) 0.044(10) Uiso 1 1 d . . . H21B H 0.798(3) 0.649(2) 0.4153(19) 0.035(9) Uiso 1 1 d . . . C28 C 0.4784(3) 0.39639(19) 0.39171(16) 0.0289(7) Uani 1 1 d . . . C29 C 0.4004(4) 0.4405(2) 0.31680(17) 0.0365(7) Uani 1 1 d . . . H29A H 0.4623 0.4237 0.2787 0.055 Uiso 1 1 calc R . . H29B H 0.3837 0.5000 0.3059 0.055 Uiso 1 1 calc R . . H29C H 0.3043 0.4266 0.3168 0.055 Uiso 1 1 calc R . . O22 O 0.4797(3) 0.32464(14) 0.42558(12) 0.0442(6) Uani 1 1 d . . . N22 N 0.5463(3) 0.44201(16) 0.41717(13) 0.0279(6) Uani 1 1 d . . . H22 H 0.556(4) 0.491(2) 0.387(2) 0.044(10) Uiso 1 1 d . . . C31 C 0.4153(3) 0.02369(17) 0.59251(16) 0.0274(6) Uani 1 1 d . . . C32 C 0.3940(3) 0.10459(18) 0.54188(16) 0.0282(6) Uani 1 1 d . . . C33 C 0.4544(4) 0.1596(2) 0.56135(17) 0.0366(8) Uani 1 1 d . . . H33 H 0.438(3) 0.210(2) 0.5321(19) 0.036(9) Uiso 1 1 d . . . C34 C 0.5377(4) 0.1371(2) 0.62623(18) 0.0425(8) Uani 1 1 d . . . H34 H 0.581(4) 0.174(2) 0.634(2) 0.047(10) Uiso 1 1 d . . . C35 C 0.5637(4) 0.0570(2) 0.67314(19) 0.0438(9) Uani 1 1 d . . . H35 H 0.617(4) 0.048(2) 0.716(2) 0.058(11) Uiso 1 1 d . . . C36 C 0.5033(4) 0.0012(2) 0.65722(18) 0.0376(8) Uani 1 1 d . . . H36 H 0.521(3) -0.055(2) 0.6916(18) 0.037(9) Uiso 1 1 d . . . C37 C 0.3088(3) 0.13165(18) 0.46920(16) 0.0285(6) Uani 1 1 d . . . O31 O 0.2309(2) 0.08920(13) 0.45558(11) 0.0364(5) Uani 1 1 d . . . N31 N 0.3186(3) 0.20204(17) 0.41855(16) 0.0346(6) Uani 1 1 d . . . H31A H 0.377(4) 0.234(2) 0.425(2) 0.048(11) Uiso 1 1 d . . . H31B H 0.268(4) 0.2139(19) 0.3809(19) 0.031(9) Uiso 1 1 d . . . C38 C 0.3353(4) -0.10692(18) 0.62073(17) 0.0340(7) Uani 1 1 d . . . C39 C 0.2516(4) -0.1481(2) 0.58497(19) 0.0431(8) Uani 1 1 d . . . H39A H 0.3163 -0.2006 0.5841 0.065 Uiso 1 1 calc R . . H39B H 0.2201 -0.1125 0.5340 0.065 Uiso 1 1 calc R . . H39C H 0.1636 -0.1582 0.6135 0.065 Uiso 1 1 calc R . . O32 O 0.3867(3) -0.13948(14) 0.68453(12) 0.0482(6) Uani 1 1 d . . . N32 N 0.3491(3) -0.03220(15) 0.57619(15) 0.0325(6) Uani 1 1 d . . . H32 H 0.309(4) -0.013(2) 0.535(2) 0.038(10) Uiso 1 1 d . . . C41 C 0.4455(3) 0.25072(16) 0.03076(16) 0.0250(6) Uani 1 1 d . . . C42 C 0.4636(3) 0.24948(16) 0.10441(16) 0.0250(6) Uani 1 1 d . . . C43 C 0.4059(3) 0.19387(18) 0.16146(17) 0.0274(6) Uani 1 1 d . . . H43 H 0.418(3) 0.1950(17) 0.2102(18) 0.026(8) Uiso 1 1 d . . . C44 C 0.3311(3) 0.14181(19) 0.14710(18) 0.0306(7) Uani 1 1 d . . . H44 H 0.292(3) 0.1074(18) 0.1840(17) 0.026(8) Uiso 1 1 d . . . C45 C 0.3100(3) 0.14564(19) 0.07483(18) 0.0331(7) Uani 1 1 d . . . H45 H 0.261(3) 0.1111(19) 0.0641(17) 0.029(8) Uiso 1 1 d . . . C46 C 0.3665(3) 0.19877(18) 0.01721(18) 0.0305(7) Uani 1 1 d . . . H46 H 0.353(3) 0.2001(17) -0.0304(18) 0.028(8) Uiso 1 1 d . . . C47 C 0.5372(3) 0.30817(17) 0.12143(16) 0.0259(6) Uani 1 1 d . . . O41 O 0.5495(2) 0.37250(12) 0.07216(11) 0.0299(5) Uani 1 1 d . . . N41 N 0.5822(3) 0.29251(18) 0.19123(14) 0.0324(6) Uani 1 1 d . . . H41A H 0.631(4) 0.331(2) 0.201(2) 0.060(12) Uiso 1 1 d . . . H41B H 0.585(4) 0.248(2) 0.226(2) 0.040(10) Uiso 1 1 d . . . C48 C 0.5325(3) 0.30359(18) -0.09685(16) 0.0288(7) Uani 1 1 d . . . C49 C 0.5909(4) 0.3739(2) -0.14678(18) 0.0405(8) Uani 1 1 d . . . H49A H 0.6967 0.3539 -0.1550 0.061 Uiso 1 1 calc R . . H49B H 0.5796 0.4165 -0.1232 0.061 Uiso 1 1 calc R . . H49C H 0.5346 0.3971 -0.1946 0.061 Uiso 1 1 calc R . . O42 O 0.5150(2) 0.24856(13) -0.11882(12) 0.0369(5) Uani 1 1 d . . . N42 N 0.5018(3) 0.30658(16) -0.02757(13) 0.0286(6) Uani 1 1 d . . . H42 H 0.517(4) 0.344(2) -0.016(2) 0.041(10) Uiso 1 1 d . . . C51 C 0.7793(3) 0.91591(18) 0.23821(16) 0.0275(6) Uani 1 1 d . . . C52 C 0.7166(3) 0.85838(17) 0.22166(16) 0.0285(7) Uani 1 1 d . . . C53 C 0.6364(4) 0.8835(2) 0.15425(18) 0.0376(8) Uani 1 1 d . . . H53 H 0.593(3) 0.848(2) 0.1411(18) 0.034(9) Uiso 1 1 d . . . C54 C 0.6156(4) 0.9620(2) 0.1050(2) 0.0450(9) Uani 1 1 d . . . H54 H 0.566(4) 0.976(2) 0.056(2) 0.062(11) Uiso 1 1 d . . . C55 C 0.6722(4) 1.0183(2) 0.12299(19) 0.0426(9) Uani 1 1 d . . . H55 H 0.657(3) 1.074(2) 0.0908(18) 0.039(9) Uiso 1 1 d . . . C56 C 0.7533(4) 0.99587(19) 0.18886(19) 0.0368(8) Uani 1 1 d . . . H56 H 0.787(4) 1.038(2) 0.2025(19) 0.043(9) Uiso 1 1 d . . . C57 C 0.7289(3) 0.77379(17) 0.27559(16) 0.0274(6) Uani 1 1 d . . . O51 O 0.8148(2) 0.74566(12) 0.33170(12) 0.0382(5) Uani 1 1 d . . . N51 N 0.6444(3) 0.72841(17) 0.26273(16) 0.0330(6) Uani 1 1 d . . . H51A H 0.594(4) 0.743(2) 0.225(2) 0.040(10) Uiso 1 1 d . . . H51B H 0.653(3) 0.678(2) 0.2958(19) 0.033(9) Uiso 1 1 d . . . C58 C 0.9469(3) 0.93148(18) 0.32852(17) 0.0322(7) Uani 1 1 d . . . C59 C 1.0247(4) 0.8849(2) 0.40306(17) 0.0379(8) Uani 1 1 d . . . H59A H 1.1260 0.8928 0.4018 0.057 Uiso 1 1 calc R . . H59B H 1.0295 0.8262 0.4150 0.057 Uiso 1 1 calc R . . H59C H 0.9695 0.9053 0.4411 0.057 Uiso 1 1 calc R . . O52 O 0.9621(3) 0.99964(14) 0.29279(15) 0.0591(8) Uani 1 1 d . . . N52 N 0.8616(3) 0.89165(16) 0.30521(14) 0.0304(6) Uani 1 1 d . . . H52 H 0.862(4) 0.841(2) 0.333(2) 0.048(10) Uiso 1 1 d . . . C1S C 0.8130(7) 0.0657(3) 0.8537(3) 0.0916(17) Uani 1 1 d D . . Cl1S Cl 0.78718(16) 0.15492(9) 0.77653(6) 0.0976(5) Uani 1 1 d . A . C2S C 0.8089(6) 0.0818(3) 0.9239(3) 0.0609(14) Uiso 0.75 1 d PD A 1 Cl2S Cl 0.9466(3) 0.12317(15) 0.94352(14) 0.1019(8) Uiso 0.75 1 d PD A 1 C2T C 0.916(2) 0.0545(9) 0.9121(9) 0.084(6) Uiso 0.25 1 d PD A 2 Cl2T Cl 0.9966(5) 0.1266(3) 0.9277(3) 0.0508(11) Uiso 0.25 1 d PD A 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 C1 0.0254(14) 0.0242(14) 0.0230(15) -0.0074(11) -0.0024(11) -0.0049(11) C2 0.0277(14) 0.0257(15) 0.0211(14) -0.0056(12) -0.0004(11) -0.0079(11) C3 0.0394(17) 0.0297(16) 0.0254(16) -0.0019(13) -0.0023(13) -0.0176(13) C4 0.0420(18) 0.0369(18) 0.0365(19) -0.0110(15) -0.0045(15) -0.0219(15) C5 0.0356(17) 0.0392(18) 0.0208(16) -0.0076(13) -0.0081(13) -0.0120(13) C6 0.0348(16) 0.0280(16) 0.0226(15) -0.0026(13) -0.0029(12) -0.0096(12) C7 0.0321(15) 0.0282(15) 0.0175(14) -0.0057(12) 0.0011(11) -0.0109(12) O1 0.0542(13) 0.0283(11) 0.0200(10) -0.0051(9) -0.0067(9) -0.0167(10) N1 0.0534(17) 0.0311(15) 0.0204(14) -0.0024(11) -0.0074(12) -0.0192(13) C8 0.0318(15) 0.0245(15) 0.0246(16) -0.0064(12) -0.0029(12) -0.0080(12) C9 0.0402(17) 0.0288(16) 0.0319(17) -0.0091(13) -0.0028(14) -0.0131(13) O2 0.0718(17) 0.0561(15) 0.0212(12) -0.0054(10) 0.0014(11) -0.0414(13) N2 0.0399(14) 0.0236(13) 0.0174(13) -0.0045(10) -0.0045(11) -0.0115(10) C11 0.0298(14) 0.0224(14) 0.0207(14) -0.0082(11) -0.0002(11) -0.0086(11) C12 0.0273(14) 0.0256(14) 0.0218(14) -0.0094(12) 0.0004(11) -0.0072(11) C13 0.0321(16) 0.0277(15) 0.0198(15) -0.0064(12) -0.0048(12) -0.0072(12) C14 0.0362(16) 0.0257(16) 0.0288(16) -0.0071(13) -0.0011(13) -0.0092(13) C15 0.0374(17) 0.0275(16) 0.0298(17) -0.0135(13) -0.0015(13) -0.0128(13) C16 0.0366(16) 0.0308(16) 0.0223(16) -0.0109(13) -0.0041(13) -0.0115(13) C17 0.0259(14) 0.0249(14) 0.0246(15) -0.0073(12) -0.0033(11) -0.0093(11) O11 0.0462(13) 0.0369(12) 0.0220(11) -0.0072(9) -0.0018(9) -0.0243(10) N11 0.0399(15) 0.0296(14) 0.0203(13) -0.0050(11) -0.0043(11) -0.0174(12) C18 0.0328(15) 0.0294(15) 0.0210(15) -0.0093(12) -0.0010(12) -0.0069(12) C19 0.0437(18) 0.0317(16) 0.0216(15) -0.0078(13) -0.0005(13) -0.0126(13) O12 0.0478(13) 0.0394(13) 0.0263(12) -0.0042(9) -0.0123(10) -0.0186(10) N12 0.0372(14) 0.0260(13) 0.0207(13) -0.0069(10) -0.0047(11) -0.0139(11) C21 0.0298(15) 0.0263(15) 0.0210(14) -0.0062(12) -0.0031(11) -0.0087(11) C22 0.0280(14) 0.0262(15) 0.0241(15) -0.0084(12) -0.0015(12) -0.0075(11) C23 0.0404(18) 0.0275(16) 0.0333(17) -0.0084(13) -0.0082(14) -0.0132(14) C24 0.057(2) 0.0369(18) 0.0284(18) -0.0037(14) -0.0205(16) -0.0138(16) C25 0.065(2) 0.0328(18) 0.0247(17) 0.0031(14) -0.0157(16) -0.0227(16) C26 0.0455(19) 0.0342(17) 0.0271(17) -0.0056(13) -0.0070(14) -0.0218(15) C27 0.0271(14) 0.0280(15) 0.0253(16) -0.0100(12) -0.0017(12) -0.0088(12) O21 0.0436(12) 0.0315(11) 0.0240(11) -0.0061(9) -0.0057(9) -0.0171(9) N21 0.0461(16) 0.0315(15) 0.0257(15) -0.0029(12) -0.0104(12) -0.0186(12) C28 0.0316(15) 0.0342(17) 0.0240(15) -0.0074(13) -0.0006(12) -0.0163(13) C29 0.0420(18) 0.0436(19) 0.0259(16) -0.0059(14) -0.0071(14) -0.0203(15) O22 0.0688(16) 0.0365(13) 0.0306(12) -0.0013(10) -0.0130(11) -0.0293(11) N22 0.0357(14) 0.0280(14) 0.0208(13) -0.0018(11) -0.0061(10) -0.0162(11) C31 0.0333(15) 0.0281(15) 0.0223(15) -0.0091(12) 0.0033(12) -0.0094(12) C32 0.0330(15) 0.0319(16) 0.0206(14) -0.0060(12) 0.0010(12) -0.0126(12) C33 0.057(2) 0.0322(18) 0.0217(16) -0.0012(14) -0.0012(14) -0.0222(15) C34 0.062(2) 0.045(2) 0.0287(18) -0.0077(15) -0.0043(16) -0.0316(18) C35 0.057(2) 0.050(2) 0.0238(17) -0.0063(15) -0.0128(16) -0.0180(17) C36 0.053(2) 0.0322(18) 0.0248(16) -0.0019(14) -0.0089(14) -0.0142(15) C37 0.0338(16) 0.0299(16) 0.0221(15) -0.0060(12) -0.0002(12) -0.0114(12) O31 0.0527(14) 0.0342(12) 0.0237(11) -0.0020(9) -0.0064(10) -0.0216(10) N31 0.0440(16) 0.0331(15) 0.0246(15) 0.0008(12) -0.0104(13) -0.0175(13) C38 0.0446(18) 0.0278(16) 0.0277(17) -0.0057(13) 0.0002(14) -0.0097(13) C39 0.056(2) 0.0337(18) 0.0384(19) -0.0044(15) -0.0037(16) -0.0187(16) O32 0.0742(17) 0.0353(13) 0.0283(13) 0.0057(10) -0.0112(12) -0.0208(12) N32 0.0472(16) 0.0281(14) 0.0207(14) -0.0029(11) -0.0068(12) -0.0117(11) C41 0.0250(14) 0.0224(14) 0.0264(15) -0.0054(11) -0.0032(11) -0.0061(11) C42 0.0251(14) 0.0229(14) 0.0260(15) -0.0064(12) -0.0048(11) -0.0049(11) C43 0.0298(15) 0.0292(16) 0.0226(16) -0.0072(12) -0.0011(12) -0.0072(12) C44 0.0294(15) 0.0269(16) 0.0344(18) -0.0053(13) 0.0031(13) -0.0114(12) C45 0.0331(16) 0.0278(16) 0.0408(19) -0.0093(14) -0.0056(14) -0.0131(13) C46 0.0345(16) 0.0304(16) 0.0290(17) -0.0094(13) -0.0074(13) -0.0113(13) C47 0.0269(14) 0.0272(15) 0.0240(15) -0.0094(12) 0.0004(12) -0.0063(11) O41 0.0417(12) 0.0277(11) 0.0218(10) -0.0047(9) -0.0031(9) -0.0148(9) N41 0.0478(16) 0.0284(15) 0.0221(14) -0.0046(12) -0.0078(12) -0.0146(12) C48 0.0282(15) 0.0340(16) 0.0254(16) -0.0103(13) -0.0062(12) -0.0076(12) C49 0.054(2) 0.0430(19) 0.0283(17) -0.0090(15) 0.0046(15) -0.0232(16) O42 0.0484(13) 0.0383(13) 0.0301(12) -0.0157(10) 0.0002(10) -0.0153(10) N42 0.0406(15) 0.0271(14) 0.0213(13) -0.0073(11) -0.0035(11) -0.0145(11) C51 0.0286(15) 0.0294(15) 0.0237(15) -0.0053(12) -0.0055(12) -0.0089(12) C52 0.0335(16) 0.0243(15) 0.0275(16) -0.0076(12) -0.0042(12) -0.0069(12) C53 0.051(2) 0.0325(17) 0.0314(18) -0.0068(14) -0.0129(15) -0.0161(15) C54 0.056(2) 0.0394(19) 0.0351(19) 0.0006(15) -0.0217(17) -0.0176(16) C55 0.051(2) 0.0278(17) 0.0393(19) 0.0071(15) -0.0168(16) -0.0132(15) C56 0.0415(18) 0.0269(17) 0.0412(19) -0.0049(14) -0.0122(15) -0.0130(14) C57 0.0328(15) 0.0250(15) 0.0263(15) -0.0089(12) -0.0041(12) -0.0090(12) O51 0.0514(13) 0.0293(11) 0.0312(12) 0.0010(9) -0.0173(10) -0.0166(10) N51 0.0437(16) 0.0286(15) 0.0265(15) -0.0039(12) -0.0102(13) -0.0133(12) C58 0.0391(17) 0.0287(17) 0.0298(17) -0.0075(13) -0.0065(13) -0.0115(13) C59 0.0477(19) 0.0356(18) 0.0309(17) -0.0053(14) -0.0091(14) -0.0165(15) O52 0.087(2) 0.0337(14) 0.0552(16) 0.0064(12) -0.0383(14) -0.0324(13) N52 0.0388(14) 0.0245(13) 0.0266(13) -0.0001(11) -0.0078(11) -0.0149(11) C1S 0.116(4) 0.088(4) 0.063(3) 0.003(3) -0.021(3) -0.045(3) Cl1S 0.1016(10) 0.1129(11) 0.0376(6) 0.0024(6) 0.0010(6) 0.0109(8) _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 C6 1.393(4) . ? C1 N2 1.400(4) . ? C1 C2 1.412(4) . ? C2 C3 1.393(4) . ? C2 C7 1.491(4) . ? C3 C4 1.378(4) . ? C3 H3 0.91(3) . ? C4 C5 1.371(5) . ? C4 H4 0.87(4) . ? C5 C6 1.382(4) . ? C5 H5 0.86(3) . ? C6 H6 0.98(3) . ? C7 O1 1.248(3) . ? C7 N1 1.330(4) . ? N1 H1A 0.86(4) . ? N1 H1B 0.87(4) . ? C8 O2 1.218(3) . ? C8 N2 1.352(4) . ? C8 C9 1.501(4) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? N2 H2 0.82(3) . ? C11 C16 1.394(4) . ? C11 N12 1.405(4) . ? C11 C12 1.417(4) . ? C12 C13 1.394(4) . ? C12 C17 1.496(4) . ? C13 C14 1.383(4) . ? C13 H13 0.90(3) . ? C14 C15 1.379(4) . ? C14 H14 0.97(3) . ? C15 C16 1.381(4) . ? C15 H15 0.96(4) . ? C16 H16 0.90(3) . ? C17 O11 1.251(3) . ? C17 N11 1.330(4) . ? N11 H11A 0.88(4) . ? N11 H11B 0.87(4) . ? C18 O12 1.227(4) . ? C18 N12 1.354(4) . ? C18 C19 1.498(4) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? N12 H12 0.83(3) . ? C21 C26 1.397(4) . ? C21 C22 1.409(4) . ? C21 N22 1.410(4) . ? C22 C23 1.390(4) . ? C22 C27 1.495(4) . ? C23 C24 1.382(5) . ? C23 H23 0.93(3) . ? C24 C25 1.384(5) . ? C24 H24 0.90(4) . ? C25 C26 1.370(4) . ? C25 H25 0.96(4) . ? C26 H26 0.92(3) . ? C27 O21 1.249(3) . ? C27 N21 1.329(4) . ? N21 H21A 0.87(4) . ? N21 H21B 0.95(3) . ? C28 O22 1.222(4) . ? C28 N22 1.348(4) . ? C28 C29 1.500(4) . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? N22 H22 0.89(4) . ? C31 C36 1.395(4) . ? C31 N32 1.404(4) . ? C31 C32 1.415(4) . ? C32 C33 1.387(4) . ? C32 C37 1.497(4) . ? C33 C34 1.374(5) . ? C33 H33 0.86(3) . ? C34 C35 1.377(5) . ? C34 H34 0.89(4) . ? C35 C36 1.367(5) . ? C35 H35 0.93(4) . ? C36 H36 0.97(3) . ? C37 O31 1.252(4) . ? C37 N31 1.326(4) . ? N31 H31A 0.91(4) . ? N31 H31B 0.81(3) . ? C38 O32 1.221(4) . ? C38 N32 1.354(4) . ? C38 C39 1.499(5) . ? C39 H39A 0.9800 . ? C39 H39B 0.9800 . ? C39 H39C 0.9800 . ? N32 H32 0.82(4) . ? C41 C46 1.397(4) . ? C41 N42 1.405(4) . ? C41 C42 1.410(4) . ? C42 C43 1.396(4) . ? C42 C47 1.497(4) . ? C43 C44 1.379(4) . ? C43 H43 0.95(3) . ? C44 C45 1.374(5) . ? C44 H44 0.90(3) . ? C45 C46 1.373(4) . ? C45 H45 0.92(3) . ? C46 H46 0.91(3) . ? C47 O41 1.246(3) . ? C47 N41 1.328(4) . ? N41 H41A 0.97(4) . ? N41 H41B 0.85(4) . ? C48 O42 1.226(3) . ? C48 N42 1.351(4) . ? C48 C49 1.506(4) . ? C49 H49A 0.9800 . ? C49 H49B 0.9800 . ? C49 H49C 0.9800 . ? N42 H42 0.81(4) . ? C51 C56 1.391(4) . ? C51 N52 1.399(4) . ? C51 C52 1.412(4) . ? C52 C53 1.394(4) . ? C52 C57 1.497(4) . ? C53 C54 1.374(5) . ? C53 H53 0.93(3) . ? C54 C55 1.373(5) . ? C54 H54 0.98(4) . ? C55 C56 1.379(5) . ? C55 H55 0.95(3) . ? C56 H56 0.99(4) . ? C57 O51 1.246(3) . ? C57 N51 1.332(4) . ? N51 H51A 0.81(4) . ? N51 H51B 0.90(3) . ? C58 O52 1.218(4) . ? C58 N52 1.352(4) . ? C58 C59 1.498(4) . ? C59 H59A 0.9800 . ? C59 H59B 0.9800 . ? C59 H59C 0.9800 . ? N52 H52 0.89(4) . ? C1S C2T 1.431(11) . ? C1S C2S 1.451(7) . ? C1S Cl1S 1.745(5) . ? C2S Cl2S 1.728(6) . ? C2T Cl2T 1.734(10) . ? 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 C1 N2 120.9(3) . . ? C6 C1 C2 119.6(3) . . ? N2 C1 C2 119.5(2) . . ? C3 C2 C1 118.1(3) . . ? C3 C2 C7 120.1(3) . . ? C1 C2 C7 121.7(3) . . ? C4 C3 C2 121.9(3) . . ? C4 C3 H3 118(2) . . ? C2 C3 H3 120(2) . . ? C5 C4 C3 119.4(3) . . ? C5 C4 H4 123(2) . . ? C3 C4 H4 118(2) . . ? C4 C5 C6 120.8(3) . . ? C4 C5 H5 117(2) . . ? C6 C5 H5 122(2) . . ? C5 C6 C1 120.3(3) . . ? C5 C6 H6 120.2(18) . . ? C1 C6 H6 119.5(18) . . ? O1 C7 N1 119.8(3) . . ? O1 C7 C2 121.7(2) . . ? N1 C7 C2 118.5(3) . . ? C7 N1 H1A 114(2) . . ? C7 N1 H1B 126(2) . . ? H1A N1 H1B 119(3) . . ? O2 C8 N2 123.5(3) . . ? O2 C8 C9 121.1(3) . . ? N2 C8 C9 115.4(3) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 N2 C1 128.2(3) . . ? C8 N2 H2 117(2) . . ? C1 N2 H2 114(2) . . ? C16 C11 N12 122.2(3) . . ? C16 C11 C12 119.2(3) . . ? N12 C11 C12 118.5(2) . . ? C13 C12 C11 118.1(3) . . ? C13 C12 C17 120.0(3) . . ? C11 C12 C17 121.9(2) . . ? C14 C13 C12 122.0(3) . . ? C14 C13 H13 124.4(19) . . ? C12 C13 H13 113.5(19) . . ? C15 C14 C13 119.2(3) . . ? C15 C14 H14 121.1(19) . . ? C13 C14 H14 119.6(19) . . ? C14 C15 C16 120.6(3) . . ? C14 C15 H15 123(2) . . ? C16 C15 H15 116(2) . . ? C15 C16 C11 120.8(3) . . ? C15 C16 H16 118(2) . . ? C11 C16 H16 122(2) . . ? O11 C17 N11 120.2(3) . . ? O11 C17 C12 121.3(2) . . ? N11 C17 C12 118.4(3) . . ? C17 N11 H11A 120(2) . . ? C17 N11 H11B 116(2) . . ? H11A N11 H11B 121(3) . . ? O12 C18 N12 123.6(3) . . ? O12 C18 C19 122.1(3) . . ? N12 C18 C19 114.3(3) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C18 N12 C11 129.9(3) . . ? C18 N12 H12 119(2) . . ? C11 N12 H12 111(2) . . ? C26 C21 C22 119.4(3) . . ? C26 C21 N22 120.8(3) . . ? C22 C21 N22 119.8(2) . . ? C23 C22 C21 118.4(3) . . ? C23 C22 C27 119.7(3) . . ? C21 C22 C27 121.9(2) . . ? C24 C23 C22 121.9(3) . . ? C24 C23 H23 122(2) . . ? C22 C23 H23 116(2) . . ? C23 C24 C25 118.5(3) . . ? C23 C24 H24 118(3) . . ? C25 C24 H24 124(3) . . ? C26 C25 C24 121.4(3) . . ? C26 C25 H25 120(2) . . ? C24 C25 H25 119(2) . . ? C25 C26 C21 120.1(3) . . ? C25 C26 H26 122.1(18) . . ? C21 C26 H26 117.8(18) . . ? O21 C27 N21 120.4(3) . . ? O21 C27 C22 121.2(3) . . ? N21 C27 C22 118.3(3) . . ? C27 N21 H21A 120(2) . . ? C27 N21 H21B 120(2) . . ? H21A N21 H21B 120(3) . . ? O22 C28 N22 123.9(3) . . ? O22 C28 C29 121.6(3) . . ? N22 C28 C29 114.6(3) . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C28 N22 C21 128.7(3) . . ? C28 N22 H22 120(2) . . ? C21 N22 H22 110(2) . . ? C36 C31 N32 121.6(3) . . ? C36 C31 C32 119.0(3) . . ? N32 C31 C32 119.4(3) . . ? C33 C32 C31 118.1(3) . . ? C33 C32 C37 119.9(3) . . ? C31 C32 C37 122.0(3) . . ? C34 C33 C32 122.2(3) . . ? C34 C33 H33 119(2) . . ? C32 C33 H33 119(2) . . ? C33 C34 C35 118.9(3) . . ? C33 C34 H34 118(2) . . ? C35 C34 H34 122(2) . . ? C36 C35 C34 120.9(3) . . ? C36 C35 H35 125(2) . . ? C34 C35 H35 113(2) . . ? C35 C36 C31 120.8(3) . . ? C35 C36 H36 119.6(19) . . ? C31 C36 H36 119.6(19) . . ? O31 C37 N31 120.2(3) . . ? O31 C37 C32 121.5(3) . . ? N31 C37 C32 118.4(3) . . ? C37 N31 H31A 124(2) . . ? C37 N31 H31B 114(2) . . ? H31A N31 H31B 123(3) . . ? O32 C38 N32 124.0(3) . . ? O32 C38 C39 121.8(3) . . ? N32 C38 C39 114.3(3) . . ? C38 C39 H39A 109.5 . . ? C38 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? C38 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? C38 N32 C31 129.1(3) . . ? C38 N32 H32 118(2) . . ? C31 N32 H32 112(2) . . ? C46 C41 N42 121.5(3) . . ? C46 C41 C42 119.2(3) . . ? N42 C41 C42 119.2(3) . . ? C43 C42 C41 118.3(3) . . ? C43 C42 C47 120.3(3) . . ? C41 C42 C47 121.4(3) . . ? C44 C43 C42 121.6(3) . . ? C44 C43 H43 121.9(18) . . ? C42 C43 H43 116.4(18) . . ? C45 C44 C43 119.5(3) . . ? C45 C44 H44 120(2) . . ? C43 C44 H44 121(2) . . ? C46 C45 C44 120.7(3) . . ? C46 C45 H45 118.5(19) . . ? C44 C45 H45 120.8(19) . . ? C45 C46 C41 120.7(3) . . ? C45 C46 H46 119.8(19) . . ? C41 C46 H46 119.6(19) . . ? O41 C47 N41 120.4(3) . . ? O41 C47 C42 120.9(2) . . ? N41 C47 C42 118.6(3) . . ? C47 N41 H41A 118(2) . . ? C47 N41 H41B 124(2) . . ? H41A N41 H41B 117(3) . . ? O42 C48 N42 123.7(3) . . ? O42 C48 C49 121.3(3) . . ? N42 C48 C49 114.9(3) . . ? C48 C49 H49A 109.5 . . ? C48 C49 H49B 109.5 . . ? H49A C49 H49B 109.5 . . ? C48 C49 H49C 109.5 . . ? H49A C49 H49C 109.5 . . ? H49B C49 H49C 109.5 . . ? C48 N42 C41 128.1(3) . . ? C48 N42 H42 119(3) . . ? C41 N42 H42 113(3) . . ? C56 C51 N52 121.7(3) . . ? C56 C51 C52 119.3(3) . . ? N52 C51 C52 119.0(3) . . ? C53 C52 C51 118.1(3) . . ? C53 C52 C57 120.1(3) . . ? C51 C52 C57 121.8(2) . . ? C54 C53 C52 121.9(3) . . ? C54 C53 H53 117(2) . . ? C52 C53 H53 121(2) . . ? C55 C54 C53 119.5(3) . . ? C55 C54 H54 121(2) . . ? C53 C54 H54 119(2) . . ? C54 C55 C56 120.5(3) . . ? C54 C55 H55 122(2) . . ? C56 C55 H55 118(2) . . ? C55 C56 C51 120.7(3) . . ? C55 C56 H56 119(2) . . ? C51 C56 H56 120(2) . . ? O51 C57 N51 119.9(3) . . ? O51 C57 C52 121.6(3) . . ? N51 C57 C52 118.4(3) . . ? C57 N51 H51A 123(2) . . ? C57 N51 H51B 117(2) . . ? H51A N51 H51B 120(3) . . ? O52 C58 N52 124.0(3) . . ? O52 C58 C59 121.2(3) . . ? N52 C58 C59 114.8(3) . . ? C58 C59 H59A 109.5 . . ? C58 C59 H59B 109.5 . . ? H59A C59 H59B 109.5 . . ? C58 C59 H59C 109.5 . . ? H59A C59 H59C 109.5 . . ? H59B C59 H59C 109.5 . . ? C58 N52 C51 129.4(3) . . ? C58 N52 H52 119(2) . . ? C51 N52 H52 112(2) . . ? C2T C1S Cl1S 118.6(7) . . ? C2S C1S Cl1S 113.1(4) . . ? C1S C2S Cl2S 117.8(4) . . ? C1S C2T Cl2T 128.4(10) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.9(4) . . . . ? N2 C1 C2 C3 178.6(3) . . . . ? C6 C1 C2 C7 176.1(3) . . . . ? N2 C1 C2 C7 -4.5(4) . . . . ? C1 C2 C3 C4 2.2(5) . . . . ? C7 C2 C3 C4 -174.8(3) . . . . ? C2 C3 C4 C5 -1.8(5) . . . . ? C3 C4 C5 C6 0.0(5) . . . . ? C4 C5 C6 C1 1.3(5) . . . . ? N2 C1 C6 C5 179.7(3) . . . . ? C2 C1 C6 C5 -0.8(4) . . . . ? C3 C2 C7 O1 -170.1(3) . . . . ? C1 C2 C7 O1 13.0(4) . . . . ? C3 C2 C7 N1 11.6(4) . . . . ? C1 C2 C7 N1 -165.3(3) . . . . ? O2 C8 N2 C1 0.8(5) . . . . ? C9 C8 N2 C1 -179.1(3) . . . . ? C6 C1 N2 C8 -21.2(4) . . . . ? C2 C1 N2 C8 159.3(3) . . . . ? C16 C11 C12 C13 0.3(4) . . . . ? N12 C11 C12 C13 -179.6(3) . . . . ? C16 C11 C12 C17 178.9(3) . . . . ? N12 C11 C12 C17 -1.1(4) . . . . ? C11 C12 C13 C14 -0.1(4) . . . . ? C17 C12 C13 C14 -178.7(3) . . . . ? C12 C13 C14 C15 0.0(5) . . . . ? C13 C14 C15 C16 0.1(5) . . . . ? C14 C15 C16 C11 0.1(5) . . . . ? N12 C11 C16 C15 179.6(3) . . . . ? C12 C11 C16 C15 -0.3(4) . . . . ? C13 C12 C17 O11 161.1(3) . . . . ? C11 C12 C17 O11 -17.4(4) . . . . ? C13 C12 C17 N11 -17.6(4) . . . . ? C11 C12 C17 N11 163.9(3) . . . . ? O12 C18 N12 C11 1.8(5) . . . . ? C19 C18 N12 C11 -179.2(3) . . . . ? C16 C11 N12 C18 8.1(5) . . . . ? C12 C11 N12 C18 -171.9(3) . . . . ? C26 C21 C22 C23 6.3(4) . . . . ? N22 C21 C22 C23 -174.6(3) . . . . ? C26 C21 C22 C27 -174.3(3) . . . . ? N22 C21 C22 C27 4.8(4) . . . . ? C21 C22 C23 C24 -3.0(5) . . . . ? C27 C22 C23 C24 177.6(3) . . . . ? C22 C23 C24 C25 -1.8(5) . . . . ? C23 C24 C25 C26 3.4(6) . . . . ? C24 C25 C26 C21 0.0(6) . . . . ? C22 C21 C26 C25 -4.9(5) . . . . ? N22 C21 C26 C25 176.1(3) . . . . ? C23 C22 C27 O21 164.8(3) . . . . ? C21 C22 C27 O21 -14.6(4) . . . . ? C23 C22 C27 N21 -15.6(4) . . . . ? C21 C22 C27 N21 165.0(3) . . . . ? O22 C28 N22 C21 1.7(5) . . . . ? C29 C28 N22 C21 -177.7(3) . . . . ? C26 C21 N22 C28 -17.8(5) . . . . ? C22 C21 N22 C28 163.1(3) . . . . ? C36 C31 C32 C33 -4.0(4) . . . . ? N32 C31 C32 C33 176.7(3) . . . . ? C36 C31 C32 C37 176.2(3) . . . . ? N32 C31 C32 C37 -3.1(4) . . . . ? C31 C32 C33 C34 2.4(5) . . . . ? C37 C32 C33 C34 -177.8(3) . . . . ? C32 C33 C34 C35 0.8(6) . . . . ? C33 C34 C35 C36 -2.5(6) . . . . ? C34 C35 C36 C31 0.9(6) . . . . ? N32 C31 C36 C35 -178.3(3) . . . . ? C32 C31 C36 C35 2.4(5) . . . . ? C33 C32 C37 O31 -167.0(3) . . . . ? C31 C32 C37 O31 12.8(4) . . . . ? C33 C32 C37 N31 13.6(4) . . . . ? C31 C32 C37 N31 -166.7(3) . . . . ? O32 C38 N32 C31 -3.0(5) . . . . ? C39 C38 N32 C31 177.5(3) . . . . ? C36 C31 N32 C38 12.0(5) . . . . ? C32 C31 N32 C38 -168.7(3) . . . . ? C46 C41 C42 C43 2.2(4) . . . . ? N42 C41 C42 C43 179.6(2) . . . . ? C46 C41 C42 C47 -175.4(3) . . . . ? N42 C41 C42 C47 1.9(4) . . . . ? C41 C42 C43 C44 -0.9(4) . . . . ? C47 C42 C43 C44 176.8(3) . . . . ? C42 C43 C44 C45 -1.3(4) . . . . ? C43 C44 C45 C46 2.1(5) . . . . ? C44 C45 C46 C41 -0.7(5) . . . . ? N42 C41 C46 C45 -178.8(3) . . . . ? C42 C41 C46 C45 -1.5(4) . . . . ? C43 C42 C47 O41 -158.6(3) . . . . ? C41 C42 C47 O41 19.0(4) . . . . ? C43 C42 C47 N41 17.8(4) . . . . ? C41 C42 C47 N41 -164.6(3) . . . . ? O42 C48 N42 C41 -0.5(5) . . . . ? C49 C48 N42 C41 179.5(3) . . . . ? C46 C41 N42 C48 -22.2(4) . . . . ? C42 C41 N42 C48 160.5(3) . . . . ? C56 C51 C52 C53 2.9(5) . . . . ? N52 C51 C52 C53 -179.3(3) . . . . ? C56 C51 C52 C57 -174.4(3) . . . . ? N52 C51 C52 C57 3.3(4) . . . . ? C51 C52 C53 C54 -0.9(5) . . . . ? C57 C52 C53 C54 176.4(3) . . . . ? C52 C53 C54 C55 -1.6(6) . . . . ? C53 C54 C55 C56 2.1(6) . . . . ? C54 C55 C56 C51 0.0(6) . . . . ? N52 C51 C56 C55 179.8(3) . . . . ? C52 C51 C56 C55 -2.5(5) . . . . ? C53 C52 C57 O51 170.7(3) . . . . ? C51 C52 C57 O51 -12.1(5) . . . . ? C53 C52 C57 N51 -9.7(4) . . . . ? C51 C52 C57 N51 167.5(3) . . . . ? O52 C58 N52 C51 2.0(6) . . . . ? C59 C58 N52 C51 -177.5(3) . . . . ? C56 C51 N52 C58 -11.8(5) . . . . ? C52 C51 N52 C58 170.5(3) . . . . ? C2T C1S C2S Cl2S 43.6(8) . . . . ? Cl1S C1S C2S Cl2S -64.1(6) . . . . ? C2S C1S C2T Cl2T -79.4(16) . . . . ? Cl1S C1S C2T Cl2T 14(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A O31 0.86(4) 2.07(4) 2.922(4) 174(3) . N1 H1B O52 0.87(4) 2.10(4) 2.963(4) 173(3) 1_445 C3 H3 O52 0.91(3) 2.37(3) 3.243(4) 160(3) 1_445 N11 H11B O41 0.87(4) 2.05(4) 2.918(4) 176(3) 2_666 N11 H11A O2 0.88(4) 1.98(4) 2.854(3) 170(3) 1_556 C13 H13 O2 0.90(3) 2.49(3) 3.225(4) 139(2) 1_556 N21 H21B O51 0.95(3) 1.96(4) 2.901(3) 172(3) . N21 H21A O12 0.87(4) 2.18(4) 3.030(3) 166(3) 1_655 C23 H23 O12 0.93(3) 2.41(3) 3.250(4) 149(3) 1_655 N31 H31B O1 0.81(3) 2.13(4) 2.936(4) 174(3) . N31 H31A O22 0.91(4) 2.06(4) 2.962(4) 169(3) . C33 H33 O22 0.86(3) 2.46(3) 3.264(4) 156(3) . N41 H41A O11 0.97(4) 1.96(4) 2.932(4) 177(3) 2_666 N41 H41B O32 0.85(4) 2.08(4) 2.921(4) 173(3) 2_656 C43 H43 O32 0.95(3) 2.53(3) 3.308(4) 140(2) 2_656 N51 H51B O21 0.90(3) 1.98(4) 2.885(3) 179(3) . N51 H51A O42 0.81(4) 2.23(4) 3.027(4) 166(3) 2_665 C53 H53 O42 0.93(3) 2.33(3) 3.260(4) 175(3) 2_665 C25 H25 Cl1S 0.96(4) 2.68(4) 3.586(3) 156(3) . N2 H2 O1 0.82(3) 1.94(3) 2.623(3) 140(3) . N12 H12 O11 0.83(3) 1.91(3) 2.633(3) 146(3) . N22 H22 O21 0.89(4) 1.87(4) 2.634(3) 144(3) . N32 H32 O31 0.82(4) 1.94(3) 2.634(3) 142(3) . N42 H42 O41 0.81(4) 1.96(4) 2.633(3) 140(3) . N52 H52 O51 0.89(4) 1.85(4) 2.613(3) 144(3) . _diffrn_measured_fraction_theta_max 0.818 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.903 _refine_diff_density_max 1.114 _refine_diff_density_min -1.009 _refine_diff_density_rms 0.062 data_[(AABA)6.(Diox)] _database_code_depnum_ccdc_archive 'CCDC 294944' _audit_creation_method SHELXL-97 _chemical_name_systematic ; o-Acetamidobenzamide 1,4-Dioxane solvate (6/1) ; _chemical_name_common (C9H10N2O2)6.(C4H8O2) _chemical_melting_point ? _chemical_formula_moiety 'C9.67 H11.33 N2 O2.33' _chemical_formula_sum 'C9.67 H11.33 N2 O2.33' _chemical_formula_weight 192.87 _exptl_special_details ; The crystal underwent significant decomposition on removal from the mother liquor and oin transfer from the perfluorpolyether oil to the cold stream of the diffractomter. Several other crystals had been looked at previously but this crystal was the only one found which indexed and so a full data collection was performed. Obviously, the data is very poor and no attempt has been made to improve it. The data is included here purely to show that this solvate is isostructural with the other four; 1-propanol, 1-butanol, 2-butanol and 1,2-dichlororthane. ; 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' 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.746(10) _cell_length_b 17.664(18) _cell_length_c 18.548(19) _cell_angle_alpha 73.290(16) _cell_angle_beta 85.649(18) _cell_angle_gamma 75.83(2) _cell_volume 2965(5) _cell_formula_units_Z 12 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4619 _cell_measurement_theta_min 2.221 _cell_measurement_theta_max 27.898 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.96 _exptl_crystal_size_mid 0.79 _exptl_crystal_size_min 0.59 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.296 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1224 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.0587 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS v2.03' _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 SMART APEX diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% None _diffrn_reflns_number 23237 _diffrn_reflns_av_R_equivalents 0.2437 _diffrn_reflns_av_sigmaI/netI 0.2726 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.15 _diffrn_reflns_theta_max 29.49 _reflns_number_total 11789 _reflns_number_gt 3937 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary 'direct methods' _atom_sites_solution_secondary 'difference Fourier synthesis' _atom_sites_solution_hydrogens 'methyl H found from delta F; others geometrically placed' _refine_ls_hydrogen_treatment 'rigid rotor model for methyls; others riding model' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 11789 _refine_ls_number_parameters 757 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.3594 _refine_ls_R_factor_gt 0.2059 _refine_ls_wR_factor_ref 0.4703 _refine_ls_wR_factor_gt 0.3910 _refine_ls_goodness_of_fit_ref 1.127 _refine_ls_restrained_S_all 1.127 _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 0.0490(9) 0.2964(5) 0.1503(3) 0.045(2) Uani 1 1 d . . . C2 C 0.0370(9) 0.2242(5) 0.2073(3) 0.043(2) Uani 1 1 d . . . C3 C -0.0362(10) 0.1723(6) 0.1921(3) 0.057(2) Uani 1 1 d . . . H3A H -0.0435 0.1243 0.2303 0.068 Uiso 1 1 calc R . . C4 C -0.0996(11) 0.1884(6) 0.1223(3) 0.064(3) Uani 1 1 d . . . H4A H -0.1491 0.1521 0.1130 0.077 Uiso 1 1 calc R . . C5 C -0.0882(11) 0.2592(6) 0.0667(3) 0.062(3) Uani 1 1 d . . . H5A H -0.1299 0.2706 0.0189 0.075 Uiso 1 1 calc R . . C6 C -0.0184(10) 0.3130(5) 0.0793(3) 0.051(2) Uani 1 1 d . . . H6A H -0.0145 0.3614 0.0408 0.061 Uiso 1 1 calc R . . C7 C 0.1127(9) 0.1997(5) 0.2831(3) 0.042(2) Uani 1 1 d . . . O1 O 0.1751(7) 0.2461(3) 0.2999(2) 0.0522(16) Uani 1 1 d . . . N1 N 0.1121(7) 0.1264(4) 0.3312(3) 0.0480(18) Uani 1 1 d . . . H1A H 0.1557 0.1111 0.3746 0.058 Uiso 1 1 calc R . . H1B H 0.0680 0.0939 0.3192 0.058 Uiso 1 1 calc R . . C8 C 0.1696(10) 0.4117(5) 0.1154(3) 0.053(2) Uani 1 1 d . . . C9 C 0.2470(11) 0.4562(5) 0.1498(4) 0.058(3) Uani 1 1 d . . . H9A H 0.3432 0.4518 0.1290 0.087 Uiso 1 1 calc R . . H9B H 0.2515 0.4322 0.2045 0.087 Uiso 1 1 calc R . . H9C H 0.1970 0.5136 0.1384 0.087 Uiso 1 1 calc R . . O2 O 0.1534(8) 0.4297(4) 0.0466(2) 0.074(2) Uani 1 1 d . . . N2 N 0.1185(8) 0.3494(4) 0.1649(2) 0.0463(18) Uani 1 1 d . . . H2A H 0.1327 0.3428 0.2129 0.056 Uiso 1 1 calc R . . C11 C 0.1013(9) 0.4913(4) 0.7594(3) 0.042(2) Uani 1 1 d . . . C12 C 0.1746(9) 0.4740(5) 0.8295(3) 0.047(2) Uani 1 1 d . . . C13 C 0.1697(10) 0.4014(5) 0.8837(3) 0.051(2) Uani 1 1 d . . . H13A H 0.2155 0.3896 0.9304 0.061 Uiso 1 1 calc R . . C14 C 0.1013(10) 0.3459(5) 0.8725(3) 0.054(2) Uani 1 1 d . . . H14A H 0.1010 0.2965 0.9104 0.064 Uiso 1 1 calc R . . C15 C 0.0319(11) 0.3644(5) 0.8034(3) 0.057(3) Uani 1 1 d . . . H15A H -0.0177 0.3277 0.7949 0.069 Uiso 1 1 calc R . . C16 C 0.0352(10) 0.4355(5) 0.7477(3) 0.057(3) Uani 1 1 d . . . H16A H -0.0088 0.4460 0.7007 0.069 Uiso 1 1 calc R . . C17 C 0.2546(9) 0.5307(5) 0.8441(3) 0.048(2) Uani 1 1 d . . . O11 O 0.2941(7) 0.5838(3) 0.7915(2) 0.0564(17) Uani 1 1 d . . . N11 N 0.2831(8) 0.5223(4) 0.9163(3) 0.058(2) Uani 1 1 d . . . H11A H 0.3299 0.5544 0.9271 0.070 Uiso 1 1 calc R . . H11B H 0.2548 0.4848 0.9527 0.070 Uiso 1 1 calc R . . C18 C 0.0296(10) 0.6022(5) 0.6380(3) 0.046(2) Uani 1 1 d . . . C19 C 0.0638(10) 0.6804(5) 0.5899(3) 0.051(2) Uani 1 1 d . . . H19A H 0.0708 0.6801 0.5370 0.076 Uiso 1 1 calc R . . H19B H 0.1541 0.6852 0.6058 0.076 Uiso 1 1 calc R . . H19C H -0.0113 0.7267 0.5956 0.076 Uiso 1 1 calc R . . O12 O -0.0596(7) 0.5743(3) 0.6193(2) 0.0603(18) Uani 1 1 d . . . N12 N 0.1082(8) 0.5651(4) 0.7041(3) 0.0472(18) Uani 1 1 d . . . H12A H 0.1697 0.5906 0.7126 0.057 Uiso 1 1 calc R . . C21 C 0.6523(9) 0.4096(5) 0.5070(3) 0.045(2) Uani 1 1 d . . . C22 C 0.7444(9) 0.4573(5) 0.5132(3) 0.042(2) Uani 1 1 d . . . C23 C 0.8352(10) 0.4281(5) 0.5766(3) 0.050(2) Uani 1 1 d . . . H23A H 0.9023 0.4578 0.5804 0.060 Uiso 1 1 calc R . . C24 C 0.8293(11) 0.3581(5) 0.6331(4) 0.060(3) Uani 1 1 d . . . H24A H 0.8926 0.3397 0.6744 0.072 Uiso 1 1 calc R . . C25 C 0.7308(12) 0.3153(5) 0.6289(4) 0.068(3) Uani 1 1 d . . . H25A H 0.7232 0.2687 0.6688 0.082 Uiso 1 1 calc R . . C26 C 0.6414(11) 0.3401(5) 0.5660(3) 0.059(3) Uani 1 1 d . . . H26A H 0.5740 0.3102 0.5633 0.071 Uiso 1 1 calc R . . C27 C 0.7475(9) 0.5377(5) 0.4568(3) 0.047(2) Uani 1 1 d . . . O21 O 0.6911(7) 0.5573(3) 0.3924(2) 0.0592(18) Uani 1 1 d . . . N21 N 0.8089(8) 0.5875(4) 0.4752(3) 0.058(2) Uani 1 1 d . . . H21A H 0.8113 0.6347 0.4430 0.069 Uiso 1 1 calc R . . H21B H 0.8478 0.5738 0.5198 0.069 Uiso 1 1 calc R . . C28 C 0.5023(10) 0.3877(5) 0.4134(3) 0.047(2) Uani 1 1 d . . . C29 C 0.4282(10) 0.4316(5) 0.3389(3) 0.054(2) Uani 1 1 d . . . H29A H 0.3549 0.4046 0.3329 0.082 Uiso 1 1 calc R . . H29B H 0.4972 0.4305 0.2977 0.082 Uiso 1 1 calc R . . H29C H 0.3846 0.4881 0.3379 0.082 Uiso 1 1 calc R . . O22 O 0.5037(8) 0.3164(3) 0.4465(2) 0.0627(19) Uani 1 1 d . . . N22 N 0.5691(8) 0.4339(4) 0.4404(3) 0.0468(18) Uani 1 1 d . . . H22A H 0.5595 0.4848 0.4134 0.056 Uiso 1 1 calc R . . C31 C 0.4448(9) 0.0138(4) 0.6092(3) 0.040(2) Uani 1 1 d . . . C32 C 0.4320(9) 0.0938(4) 0.5592(3) 0.042(2) Uani 1 1 d . . . C33 C 0.5049(9) 0.1453(5) 0.5755(3) 0.050(2) Uani 1 1 d . . . H33A H 0.4944 0.1989 0.5430 0.059 Uiso 1 1 calc R . . C34 C 0.5932(10) 0.1209(5) 0.6381(3) 0.050(2) Uani 1 1 d . . . H34A H 0.6406 0.1577 0.6483 0.060 Uiso 1 1 calc R . . C35 C 0.6104(9) 0.0429(5) 0.6848(3) 0.046(2) Uani 1 1 d . . . H35A H 0.6725 0.0255 0.7266 0.055 Uiso 1 1 calc R . . C36 C 0.5388(9) -0.0105(5) 0.6719(3) 0.046(2) Uani 1 1 d . . . H36A H 0.5519 -0.0639 0.7050 0.055 Uiso 1 1 calc R . . C37 C 0.3399(9) 0.1246(5) 0.4887(3) 0.043(2) Uani 1 1 d . . . O31 O 0.2661(6) 0.0813(3) 0.4748(2) 0.0492(15) Uani 1 1 d . . . N31 N 0.3388(8) 0.1984(4) 0.4417(3) 0.0503(19) Uani 1 1 d . . . H31A H 0.2863 0.2167 0.4010 0.060 Uiso 1 1 calc R . . H31B H 0.3907 0.2285 0.4516 0.060 Uiso 1 1 calc R . . C38 C 0.3566(10) -0.1119(4) 0.6387(3) 0.046(2) Uani 1 1 d . . . C39 C 0.2637(10) -0.1516(5) 0.6058(3) 0.054(2) Uani 1 1 d . . . H39A H 0.3184 -0.1769 0.5687 0.081 Uiso 1 1 calc R . . H39B H 0.1815 -0.1103 0.5813 0.081 Uiso 1 1 calc R . . H39C H 0.2317 -0.1932 0.6463 0.081 Uiso 1 1 calc R . . O32 O 0.4181(7) -0.1487(3) 0.7002(2) 0.0604(18) Uani 1 1 d . . . N32 N 0.3719(7) -0.0375(4) 0.5951(2) 0.0432(17) Uani 1 1 d . . . H32A H 0.3284 -0.0200 0.5515 0.052 Uiso 1 1 calc R . . C41 C 0.4586(9) 0.2463(5) 0.0082(3) 0.045(2) Uani 1 1 d . . . C42 C 0.4672(9) 0.2502(5) 0.0846(3) 0.042(2) Uani 1 1 d . . . C43 C 0.4046(9) 0.1972(5) 0.1414(3) 0.045(2) Uani 1 1 d . . . H43A H 0.4090 0.1987 0.1919 0.054 Uiso 1 1 calc R . . C44 C 0.3364(9) 0.1425(5) 0.1268(3) 0.046(2) Uani 1 1 d . . . H44A H 0.2954 0.1073 0.1665 0.055 Uiso 1 1 calc R . . C45 C 0.3298(10) 0.1409(5) 0.0518(3) 0.054(2) Uani 1 1 d . . . H45A H 0.2838 0.1040 0.0407 0.065 Uiso 1 1 calc R . . C46 C 0.3888(10) 0.1919(5) -0.0056(3) 0.052(2) Uani 1 1 d . . . H46A H 0.3819 0.1901 -0.0558 0.062 Uiso 1 1 calc R . . C47 C 0.5379(9) 0.3089(5) 0.1030(3) 0.045(2) Uani 1 1 d . . . O41 O 0.5566(7) 0.3701(3) 0.0532(2) 0.0531(17) Uani 1 1 d . . . N41 N 0.5739(8) 0.2953(4) 0.1745(2) 0.052(2) Uani 1 1 d . . . H41A H 0.6116 0.3300 0.1873 0.062 Uiso 1 1 calc R . . H41B H 0.5597 0.2517 0.2088 0.062 Uiso 1 1 calc R . . C48 C 0.5331(9) 0.3066(5) -0.1252(3) 0.047(2) Uani 1 1 d . . . C49 C 0.5932(12) 0.3757(6) -0.1711(3) 0.067(3) Uani 1 1 d . . . H49A H 0.6826 0.3544 -0.1942 0.100 Uiso 1 1 calc R . . H49B H 0.6103 0.4074 -0.1385 0.100 Uiso 1 1 calc R . . H49C H 0.5261 0.4107 -0.2106 0.100 Uiso 1 1 calc R . . O42 O 0.4982(7) 0.2590(3) -0.1536(2) 0.0541(16) Uani 1 1 d . . . N42 N 0.5165(8) 0.3017(4) -0.0495(2) 0.055(2) Uani 1 1 d . . . H42A H 0.5462 0.3383 -0.0352 0.066 Uiso 1 1 calc R . . C51 C 0.7920(9) 0.9103(5) 0.2671(3) 0.042(2) Uani 1 1 d . . . C52 C 0.7259(9) 0.8539(5) 0.2525(3) 0.043(2) Uani 1 1 d . . . C53 C 0.6410(10) 0.8801(5) 0.1869(3) 0.053(2) Uani 1 1 d . . . H53A H 0.5951 0.8430 0.1761 0.064 Uiso 1 1 calc R . . C54 C 0.6223(10) 0.9574(5) 0.1381(3) 0.057(3) Uani 1 1 d . . . H54A H 0.5666 0.9722 0.0941 0.069 Uiso 1 1 calc R . . C55 C 0.6849(10) 1.0126(5) 0.1536(3) 0.050(2) Uani 1 1 d . . . H55A H 0.6700 1.0665 0.1213 0.060 Uiso 1 1 calc R . . C56 C 0.7716(9) 0.9891(5) 0.2179(3) 0.050(2) Uani 1 1 d . . . H56A H 0.8165 1.0271 0.2278 0.060 Uiso 1 1 calc R . . C57 C 0.7373(9) 0.7699(5) 0.3047(3) 0.043(2) Uani 1 1 d . . . O51 O 0.8143(7) 0.7435(3) 0.3633(2) 0.0627(19) Uani 1 1 d . . . N51 N 0.6660(8) 0.7206(4) 0.2903(3) 0.0493(18) Uani 1 1 d . . . H51A H 0.6729 0.6714 0.3208 0.059 Uiso 1 1 calc R . . H51B H 0.6119 0.7372 0.2502 0.059 Uiso 1 1 calc R . . C58 C 0.9601(10) 0.9255(5) 0.3563(3) 0.047(2) Uani 1 1 d . . . C59 C 1.0361(10) 0.8781(5) 0.4304(3) 0.053(2) Uani 1 1 d . . . H59A H 1.1106 0.9039 0.4373 0.080 Uiso 1 1 calc R . . H59B H 1.0785 0.8221 0.4293 0.080 Uiso 1 1 calc R . . H59C H 0.9682 0.8779 0.4721 0.080 Uiso 1 1 calc R . . O52 O 0.9716(7) 0.9959(4) 0.3224(3) 0.0617(18) Uani 1 1 d . . . N52 N 0.8804(8) 0.8851(4) 0.3320(3) 0.0488(19) Uani 1 1 d . . . H52A H 0.8833 0.8354 0.3605 0.059 Uiso 1 1 calc R . . O1S O 0.8446(11) 0.0329(6) 0.9453(5) 0.054(2) Uiso 0.60 1 d P A 1 C2S C 0.8094(19) 0.0404(11) 0.8853(8) 0.059(4) Uiso 0.60 1 d P A 1 C3S C 0.852(2) 0.1018(11) 0.8196(8) 0.059(4) Uiso 0.60 1 d P A 1 O4S O 0.8695(15) 0.1820(9) 0.8430(7) 0.084(4) Uiso 0.60 1 d P A 1 C5S C 0.967(2) 0.1430(11) 0.9090(9) 0.072(4) Uiso 0.60 1 d P A 1 C6S C 0.8944(17) 0.0921(10) 0.9711(7) 0.052(3) Uiso 0.60 1 d P A 1 O11S O 0.852(2) 0.1897(12) 0.8899(10) 0.076(5) Uiso 0.40 1 d P B 2 C12S C 0.931(3) 0.1491(17) 0.8372(12) 0.060(6) Uiso 0.40 1 d P B 2 C13S C 0.799(3) 0.1310(14) 0.8192(10) 0.043(5) Uiso 0.40 1 d P B 2 O14S O 0.740(2) 0.0772(12) 0.8812(8) 0.067(4) Uiso 0.40 1 d P B 2 C15S C 0.747(3) 0.0718(14) 0.9414(10) 0.053(5) Uiso 0.40 1 d P B 2 C16S C 0.817(2) 0.1288(13) 0.9610(9) 0.043(4) Uiso 0.40 1 d P 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 C1 0.082(6) 0.038(5) 0.018(2) -0.007(3) -0.003(3) -0.022(4) C2 0.073(6) 0.049(5) 0.015(2) -0.009(3) -0.007(3) -0.024(4) C3 0.091(7) 0.067(6) 0.021(3) -0.010(3) -0.005(3) -0.037(5) C4 0.106(8) 0.077(7) 0.026(3) -0.008(4) -0.014(4) -0.058(6) C5 0.099(7) 0.076(7) 0.021(3) -0.008(4) -0.011(3) -0.041(6) C6 0.093(7) 0.046(5) 0.019(3) -0.004(3) -0.010(3) -0.028(5) C7 0.082(6) 0.041(5) 0.014(2) -0.009(3) -0.003(3) -0.030(4) O1 0.101(5) 0.052(4) 0.0197(18) -0.007(2) -0.008(2) -0.047(3) N1 0.083(5) 0.046(4) 0.024(2) -0.003(3) -0.010(3) -0.036(4) C8 0.096(7) 0.041(5) 0.024(3) -0.005(3) -0.006(3) -0.024(5) C9 0.103(8) 0.044(5) 0.036(3) -0.009(3) -0.007(4) -0.035(5) O2 0.135(6) 0.074(5) 0.023(2) 0.002(2) -0.008(3) -0.062(4) N2 0.094(5) 0.039(4) 0.016(2) -0.006(2) -0.004(3) -0.037(4) C11 0.081(6) 0.034(4) 0.022(3) -0.008(3) -0.006(3) -0.030(4) C12 0.085(6) 0.046(5) 0.019(2) -0.011(3) -0.005(3) -0.031(5) C13 0.093(7) 0.040(5) 0.026(3) -0.004(3) -0.017(3) -0.028(5) C14 0.101(7) 0.042(5) 0.029(3) -0.006(3) -0.008(4) -0.039(5) C15 0.112(8) 0.040(5) 0.033(3) -0.008(3) -0.019(4) -0.040(5) C16 0.101(8) 0.056(6) 0.027(3) -0.009(3) -0.017(4) -0.040(5) C17 0.086(6) 0.047(5) 0.017(2) -0.008(3) -0.008(3) -0.028(5) O11 0.105(5) 0.056(4) 0.0219(19) -0.007(2) -0.007(2) -0.047(4) N11 0.118(6) 0.054(5) 0.018(2) 0.000(3) -0.012(3) -0.056(5) C18 0.089(7) 0.038(5) 0.020(2) -0.007(3) -0.003(3) -0.030(5) C19 0.092(7) 0.049(5) 0.024(3) -0.009(3) 0.001(3) -0.041(5) O12 0.106(5) 0.054(4) 0.039(2) -0.005(2) -0.025(3) -0.053(4) N12 0.083(5) 0.044(4) 0.023(2) -0.009(3) -0.011(3) -0.029(4) C21 0.086(6) 0.035(4) 0.022(3) -0.010(3) -0.007(3) -0.024(4) C22 0.074(6) 0.035(4) 0.023(3) -0.010(3) -0.005(3) -0.020(4) C23 0.088(7) 0.040(5) 0.035(3) -0.010(3) -0.015(3) -0.034(5) C24 0.101(8) 0.052(6) 0.038(3) -0.008(4) -0.029(4) -0.031(6) C25 0.146(10) 0.044(5) 0.032(3) 0.004(3) -0.024(4) -0.066(6) C26 0.110(8) 0.053(6) 0.027(3) -0.006(3) -0.012(4) -0.048(5) C27 0.081(6) 0.047(5) 0.020(3) -0.004(3) -0.003(3) -0.032(5) O21 0.114(5) 0.050(4) 0.026(2) -0.004(2) -0.016(3) -0.045(4) N21 0.110(6) 0.048(4) 0.027(2) -0.002(3) -0.013(3) -0.048(4) C28 0.083(6) 0.042(5) 0.021(3) -0.004(3) -0.002(3) -0.029(5) C29 0.086(7) 0.056(6) 0.027(3) -0.006(3) -0.009(3) -0.032(5) O22 0.126(6) 0.043(4) 0.032(2) 0.000(2) -0.017(3) -0.051(4) N22 0.088(5) 0.031(4) 0.026(2) -0.002(2) -0.014(3) -0.025(4) C31 0.075(6) 0.040(5) 0.016(2) -0.008(3) 0.001(3) -0.033(4) C32 0.078(6) 0.038(4) 0.011(2) -0.006(3) -0.006(3) -0.016(4) C33 0.088(7) 0.049(5) 0.020(2) -0.005(3) -0.007(3) -0.037(5) C34 0.088(7) 0.049(5) 0.024(3) -0.005(3) -0.010(3) -0.041(5) C35 0.079(6) 0.047(5) 0.023(3) -0.009(3) -0.009(3) -0.033(5) C36 0.086(6) 0.038(5) 0.021(3) 0.000(3) -0.010(3) -0.036(4) C37 0.080(6) 0.044(5) 0.010(2) -0.006(3) -0.002(3) -0.026(4) O31 0.091(4) 0.044(3) 0.0220(18) -0.003(2) -0.013(2) -0.037(3) N31 0.093(6) 0.038(4) 0.023(2) 0.003(2) -0.021(3) -0.029(4) C38 0.093(7) 0.030(4) 0.021(2) -0.005(3) 0.000(3) -0.028(4) C39 0.091(7) 0.049(5) 0.031(3) -0.009(3) -0.006(4) -0.034(5) O32 0.123(5) 0.041(3) 0.027(2) 0.003(2) -0.020(3) -0.046(4) N32 0.086(5) 0.036(4) 0.018(2) -0.002(2) -0.009(2) -0.036(4) C41 0.081(6) 0.043(5) 0.016(2) -0.005(3) -0.009(3) -0.025(4) C42 0.076(6) 0.039(5) 0.016(2) -0.003(3) -0.011(3) -0.025(4) C43 0.080(6) 0.036(5) 0.022(3) -0.006(3) -0.009(3) -0.020(4) C44 0.080(6) 0.038(5) 0.024(3) -0.001(3) -0.005(3) -0.028(4) C45 0.096(7) 0.051(5) 0.033(3) -0.011(3) -0.014(4) -0.046(5) C46 0.094(7) 0.049(5) 0.019(3) -0.005(3) -0.007(3) -0.030(5) C47 0.083(6) 0.038(5) 0.015(2) -0.004(3) -0.007(3) -0.020(4) O41 0.107(5) 0.043(3) 0.0216(19) -0.002(2) -0.014(2) -0.047(3) N41 0.104(6) 0.050(4) 0.019(2) -0.005(2) -0.008(3) -0.052(4) C48 0.084(6) 0.043(5) 0.020(2) -0.002(3) -0.009(3) -0.031(5) C49 0.132(9) 0.058(6) 0.026(3) -0.011(3) 0.007(4) -0.052(6) O42 0.105(5) 0.048(3) 0.0265(19) -0.013(2) -0.011(2) -0.042(3) N42 0.113(6) 0.054(4) 0.017(2) -0.009(3) -0.007(3) -0.053(4) C51 0.066(5) 0.045(5) 0.020(2) -0.007(3) -0.005(3) -0.023(4) C52 0.075(6) 0.043(5) 0.018(2) -0.006(3) -0.007(3) -0.026(4) C53 0.093(7) 0.048(5) 0.025(3) -0.005(3) -0.014(3) -0.030(5) C54 0.094(7) 0.057(6) 0.026(3) 0.000(3) -0.019(4) -0.036(5) C55 0.088(7) 0.037(5) 0.028(3) 0.001(3) -0.013(3) -0.029(5) C56 0.080(6) 0.049(5) 0.030(3) -0.010(3) -0.010(3) -0.031(5) C57 0.075(6) 0.038(5) 0.024(3) -0.006(3) -0.008(3) -0.027(4) O51 0.112(5) 0.046(4) 0.037(2) 0.006(2) -0.029(3) -0.043(4) N51 0.083(5) 0.047(4) 0.027(2) -0.006(3) -0.013(3) -0.035(4) C58 0.077(6) 0.045(5) 0.029(3) -0.013(3) -0.004(3) -0.029(5) C59 0.085(7) 0.055(6) 0.029(3) -0.011(3) -0.010(3) -0.030(5) O52 0.111(5) 0.044(4) 0.044(3) -0.004(3) -0.021(3) -0.049(4) N52 0.090(5) 0.043(4) 0.024(2) -0.009(3) -0.011(3) -0.033(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 N2 1.378(10) . ? C1 C2 1.427(10) . ? C1 C6 1.438(8) . ? C2 C3 1.389(11) . ? C2 C7 1.535(7) . ? C3 C4 1.401(8) . ? C3 H3A 0.9500 . ? C4 C5 1.396(12) . ? C4 H4A 0.9500 . ? C5 C6 1.374(12) . ? C5 H5A 0.9500 . ? C6 H6A 0.9500 . ? C7 O1 1.249(9) . ? C7 N1 1.344(9) . ? N1 H1A 0.8800 . ? N1 H1B 0.8800 . ? C8 O2 1.236(7) . ? C8 N2 1.385(11) . ? C8 C9 1.497(11) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? N2 H2A 0.8800 . ? C11 C16 1.373(11) . ? C11 N12 1.421(9) . ? C11 C12 1.449(7) . ? C12 C13 1.392(11) . ? C12 C17 1.502(11) . ? C13 C14 1.381(11) . ? C13 H13A 0.9500 . ? C14 C15 1.412(8) . ? C14 H14A 0.9500 . ? C15 C16 1.384(11) . ? C15 H15A 0.9500 . ? C16 H16A 0.9500 . ? C17 O11 1.254(9) . ? C17 N11 1.348(6) . ? N11 H11A 0.8800 . ? N11 H11B 0.8800 . ? C18 O12 1.213(9) . ? C18 N12 1.399(8) . ? C18 C19 1.513(11) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? N12 H12A 0.8800 . ? C21 C22 1.405(11) . ? C21 C26 1.409(11) . ? C21 N22 1.429(7) . ? C22 C23 1.421(9) . ? C22 C27 1.508(10) . ? C23 C24 1.382(11) . ? C23 H23A 0.9500 . ? C24 C25 1.378(13) . ? C24 H24A 0.9500 . ? C25 C26 1.410(9) . ? C25 H25A 0.9500 . ? C26 H26A 0.9500 . ? C27 O21 1.272(7) . ? C27 N21 1.308(10) . ? N21 H21A 0.8800 . ? N21 H21B 0.8800 . ? C28 O22 1.229(9) . ? C28 N22 1.374(10) . ? C28 C29 1.513(9) . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? N22 H22A 0.8800 . ? C31 N32 1.370(9) . ? C31 C32 1.432(10) . ? C31 C36 1.435(8) . ? C32 C33 1.389(11) . ? C32 C37 1.530(8) . ? C33 C34 1.399(8) . ? C33 H33A 0.9500 . ? C34 C35 1.379(11) . ? C34 H34A 0.9500 . ? C35 C36 1.382(11) . ? C35 H35A 0.9500 . ? C36 H36A 0.9500 . ? C37 O31 1.256(9) . ? C37 N31 1.342(9) . ? N31 H31A 0.8800 . ? N31 H31B 0.8800 . ? C38 O32 1.254(7) . ? C38 N32 1.366(9) . ? C38 C39 1.526(10) . ? C39 H39A 0.9800 . ? C39 H39B 0.9800 . ? C39 H39C 0.9800 . ? N32 H32A 0.8800 . ? C41 C46 1.392(11) . ? C41 N42 1.414(10) . ? C41 C42 1.447(7) . ? C42 C43 1.405(11) . ? C42 C47 1.502(11) . ? C43 C44 1.392(11) . ? C43 H43A 0.9500 . ? C44 C45 1.407(8) . ? C44 H44A 0.9500 . ? C45 C46 1.373(12) . ? C45 H45A 0.9500 . ? C46 H46A 0.9500 . ? C47 O41 1.245(9) . ? C47 N41 1.337(6) . ? N41 H41A 0.8800 . ? N41 H41B 0.8800 . ? C48 O42 1.234(8) . ? C48 N42 1.381(7) . ? C48 C49 1.494(12) . ? C49 H49A 0.9800 . ? C49 H49B 0.9800 . ? C49 H49C 0.9800 . ? N42 H42A 0.8800 . ? C51 C56 1.403(11) . ? C51 C52 1.407(11) . ? C51 N52 1.432(7) . ? C52 C53 1.423(8) . ? C52 C57 1.503(10) . ? C53 C54 1.381(11) . ? C53 H53A 0.9500 . ? C54 C55 1.373(11) . ? C54 H54A 0.9500 . ? C55 C56 1.415(8) . ? C55 H55A 0.9500 . ? C56 H56A 0.9500 . ? C57 O51 1.273(7) . ? C57 N51 1.331(9) . ? N51 H51A 0.8800 . ? N51 H51B 0.8800 . ? C58 O52 1.250(10) . ? C58 N52 1.352(10) . ? C58 C59 1.526(9) . ? C59 H59A 0.9800 . ? C59 H59B 0.9800 . ? C59 H59C 0.9800 . ? N52 H52A 0.8800 . ? O1S C2S 1.152(14) . ? O1S C6S 1.459(17) . ? C2S C3S 1.49(2) . ? C3S O4S 1.65(2) . ? O4S C5S 1.500(19) . ? C5S C6S 1.49(2) . ? O11S C12S 1.44(3) . ? O11S C16S 1.52(3) . ? C12S C13S 1.48(3) . ? C13S O14S 1.45(3) . ? O14S C15S 1.10(2) . ? C15S C16S 1.48(3) . ? 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 N2 C1 C2 120.1(5) . . ? N2 C1 C6 121.8(7) . . ? C2 C1 C6 118.0(7) . . ? C3 C2 C1 119.4(5) . . ? C3 C2 C7 119.3(7) . . ? C1 C2 C7 121.2(7) . . ? C2 C3 C4 122.1(8) . . ? C2 C3 H3A 118.9 . . ? C4 C3 H3A 118.9 . . ? C5 C4 C3 118.4(8) . . ? C5 C4 H4A 120.8 . . ? C3 C4 H4A 120.8 . . ? C6 C5 C4 121.7(6) . . ? C6 C5 H5A 119.2 . . ? C4 C5 H5A 119.2 . . ? C5 C6 C1 120.4(7) . . ? C5 C6 H6A 119.8 . . ? C1 C6 H6A 119.8 . . ? O1 C7 N1 120.2(5) . . ? O1 C7 C2 121.1(6) . . ? N1 C7 C2 118.7(6) . . ? C7 N1 H1A 120.0 . . ? C7 N1 H1B 120.0 . . ? H1A N1 H1B 120.0 . . ? O2 C8 N2 122.2(7) . . ? O2 C8 C9 121.4(8) . . ? N2 C8 C9 116.3(5) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C1 N2 C8 129.7(5) . . ? C1 N2 H2A 115.2 . . ? C8 N2 H2A 115.2 . . ? C16 C11 N12 123.2(5) . . ? C16 C11 C12 119.8(7) . . ? N12 C11 C12 116.9(6) . . ? C13 C12 C11 117.3(7) . . ? C13 C12 C17 120.4(5) . . ? C11 C12 C17 122.3(7) . . ? C14 C13 C12 122.9(5) . . ? C14 C13 H13A 118.5 . . ? C12 C13 H13A 118.5 . . ? C13 C14 C15 118.2(7) . . ? C13 C14 H14A 120.9 . . ? C15 C14 H14A 120.9 . . ? C16 C15 C14 120.7(7) . . ? C16 C15 H15A 119.6 . . ? C14 C15 H15A 119.6 . . ? C11 C16 C15 120.9(5) . . ? C11 C16 H16A 119.5 . . ? C15 C16 H16A 119.5 . . ? O11 C17 N11 120.9(7) . . ? O11 C17 C12 121.7(5) . . ? N11 C17 C12 117.4(7) . . ? C17 N11 H11A 120.0 . . ? C17 N11 H11B 120.0 . . ? H11A N11 H11B 120.0 . . ? O12 C18 N12 123.3(7) . . ? O12 C18 C19 121.4(6) . . ? N12 C18 C19 115.3(7) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C18 N12 C11 128.1(7) . . ? C18 N12 H12A 115.9 . . ? C11 N12 H12A 115.9 . . ? C22 C21 C26 120.2(6) . . ? C22 C21 N22 118.4(7) . . ? C26 C21 N22 121.3(7) . . ? C21 C22 C23 117.5(7) . . ? C21 C22 C27 122.7(6) . . ? C23 C22 C27 119.8(7) . . ? C24 C23 C22 122.4(8) . . ? C24 C23 H23A 118.8 . . ? C22 C23 H23A 118.8 . . ? C25 C24 C23 119.4(6) . . ? C25 C24 H24A 120.3 . . ? C23 C24 H24A 120.3 . . ? C24 C25 C26 120.5(7) . . ? C24 C25 H25A 119.7 . . ? C26 C25 H25A 119.7 . . ? C21 C26 C25 119.8(8) . . ? C21 C26 H26A 120.1 . . ? C25 C26 H26A 120.1 . . ? O21 C27 N21 120.2(7) . . ? O21 C27 C22 120.9(7) . . ? N21 C27 C22 118.9(5) . . ? C27 N21 H21A 120.0 . . ? C27 N21 H21B 120.0 . . ? H21A N21 H21B 120.0 . . ? O22 C28 N22 122.9(6) . . ? O22 C28 C29 122.7(7) . . ? N22 C28 C29 114.4(7) . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C28 N22 C21 128.0(6) . . ? C28 N22 H22A 116.0 . . ? C21 N22 H22A 116.0 . . ? N32 C31 C32 120.0(5) . . ? N32 C31 C36 122.2(6) . . ? C32 C31 C36 117.8(6) . . ? C33 C32 C31 118.8(5) . . ? C33 C32 C37 119.0(7) . . ? C31 C32 C37 122.1(7) . . ? C32 C33 C34 122.2(7) . . ? C32 C33 H33A 118.9 . . ? C34 C33 H33A 118.9 . . ? C35 C34 C33 119.2(7) . . ? C35 C34 H34A 120.4 . . ? C33 C34 H34A 120.4 . . ? C34 C35 C36 121.0(6) . . ? C34 C35 H35A 119.5 . . ? C36 C35 H35A 119.5 . . ? C35 C36 C31 120.8(7) . . ? C35 C36 H36A 119.6 . . ? C31 C36 H36A 119.6 . . ? O31 C37 N31 120.3(5) . . ? O31 C37 C32 120.5(6) . . ? N31 C37 C32 119.2(7) . . ? C37 N31 H31A 120.0 . . ? C37 N31 H31B 120.0 . . ? H31A N31 H31B 120.0 . . ? O32 C38 N32 124.1(7) . . ? O32 C38 C39 120.2(7) . . ? N32 C38 C39 115.6(5) . . ? C38 C39 H39A 109.5 . . ? C38 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? C38 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? C38 N32 C31 129.7(5) . . ? C38 N32 H32A 115.2 . . ? C31 N32 H32A 115.2 . . ? C46 C41 N42 123.1(5) . . ? C46 C41 C42 119.4(7) . . ? N42 C41 C42 117.4(6) . . ? C43 C42 C41 117.1(7) . . ? C43 C42 C47 120.9(5) . . ? C41 C42 C47 122.0(7) . . ? C44 C43 C42 122.9(5) . . ? C44 C43 H43A 118.6 . . ? C42 C43 H43A 118.6 . . ? C43 C44 C45 118.2(7) . . ? C43 C44 H44A 120.9 . . ? C45 C44 H44A 120.9 . . ? C46 C45 C44 120.9(7) . . ? C46 C45 H45A 119.6 . . ? C44 C45 H45A 119.6 . . ? C45 C46 C41 121.5(5) . . ? C45 C46 H46A 119.2 . . ? C41 C46 H46A 119.2 . . ? O41 C47 N41 121.5(7) . . ? O41 C47 C42 120.4(5) . . ? N41 C47 C42 118.0(6) . . ? C47 N41 H41A 120.0 . . ? C47 N41 H41B 120.0 . . ? H41A N41 H41B 120.0 . . ? O42 C48 N42 122.9(7) . . ? O42 C48 C49 122.2(5) . . ? N42 C48 C49 114.9(6) . . ? C48 C49 H49A 109.5 . . ? C48 C49 H49B 109.5 . . ? H49A C49 H49B 109.5 . . ? C48 C49 H49C 109.5 . . ? H49A C49 H49C 109.5 . . ? H49B C49 H49C 109.5 . . ? C48 N42 C41 129.3(6) . . ? C48 N42 H42A 115.3 . . ? C41 N42 H42A 115.3 . . ? C56 C51 C52 119.8(5) . . ? C56 C51 N52 121.6(7) . . ? C52 C51 N52 118.5(7) . . ? C51 C52 C53 117.3(7) . . ? C51 C52 C57 122.7(5) . . ? C53 C52 C57 120.0(7) . . ? C54 C53 C52 122.8(7) . . ? C54 C53 H53A 118.6 . . ? C52 C53 H53A 118.6 . . ? C55 C54 C53 119.5(6) . . ? C55 C54 H54A 120.3 . . ? C53 C54 H54A 120.3 . . ? C54 C55 C56 119.8(7) . . ? C54 C55 H55A 120.1 . . ? C56 C55 H55A 120.1 . . ? C51 C56 C55 120.8(7) . . ? C51 C56 H56A 119.6 . . ? C55 C56 H56A 119.6 . . ? O51 C57 N51 118.0(7) . . ? O51 C57 C52 122.0(7) . . ? N51 C57 C52 120.1(5) . . ? C57 N51 H51A 120.0 . . ? C57 N51 H51B 120.0 . . ? H51A N51 H51B 120.0 . . ? O52 C58 N52 124.1(6) . . ? O52 C58 C59 121.7(7) . . ? N52 C58 C59 114.3(7) . . ? C58 C59 H59A 109.5 . . ? C58 C59 H59B 109.5 . . ? H59A C59 H59B 109.5 . . ? C58 C59 H59C 109.5 . . ? H59A C59 H59C 109.5 . . ? H59B C59 H59C 109.5 . . ? C58 N52 C51 130.2(7) . . ? C58 N52 H52A 114.9 . . ? C51 N52 H52A 114.9 . . ? C2S O1S C6S 126.6(14) . . ? O1S C2S C3S 121.1(16) . . ? C2S C3S O4S 111.7(11) . . ? C5S O4S C3S 101.2(12) . . ? C6S C5S O4S 109.2(15) . . ? O1S C6S C5S 111.1(10) . . ? C12S O11S C16S 111.1(18) . . ? O11S C12S C13S 89.2(19) . . ? O14S C13S C12S 114.5(16) . . ? C15S O14S C13S 127(2) . . ? O14S C15S C16S 117(2) . . ? C15S C16S O11S 110.0(13) . . ? 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 N2 C1 C2 C3 178.6(7) . . . . ? C6 C1 C2 C3 1.2(12) . . . . ? N2 C1 C2 C7 -6.0(11) . . . . ? C6 C1 C2 C7 176.6(7) . . . . ? C1 C2 C3 C4 -0.2(13) . . . . ? C7 C2 C3 C4 -175.7(8) . . . . ? C2 C3 C4 C5 -0.1(14) . . . . ? C3 C4 C5 C6 -0.7(15) . . . . ? C4 C5 C6 C1 1.7(14) . . . . ? N2 C1 C6 C5 -179.3(8) . . . . ? C2 C1 C6 C5 -1.9(12) . . . . ? C3 C2 C7 O1 -177.3(7) . . . . ? C1 C2 C7 O1 7.3(11) . . . . ? C3 C2 C7 N1 3.4(11) . . . . ? C1 C2 C7 N1 -172.0(7) . . . . ? C2 C1 N2 C8 164.1(8) . . . . ? C6 C1 N2 C8 -18.5(13) . . . . ? O2 C8 N2 C1 2.3(15) . . . . ? C9 C8 N2 C1 -177.2(8) . . . . ? C16 C11 C12 C13 -2.3(12) . . . . ? N12 C11 C12 C13 -179.3(7) . . . . ? C16 C11 C12 C17 177.0(8) . . . . ? N12 C11 C12 C17 0.0(12) . . . . ? C11 C12 C13 C14 1.3(13) . . . . ? C17 C12 C13 C14 -178.0(8) . . . . ? C12 C13 C14 C15 -0.9(14) . . . . ? C13 C14 C15 C16 1.4(14) . . . . ? N12 C11 C16 C15 179.8(8) . . . . ? C12 C11 C16 C15 3.0(14) . . . . ? C14 C15 C16 C11 -2.6(15) . . . . ? C13 C12 C17 O11 160.2(8) . . . . ? C11 C12 C17 O11 -19.1(13) . . . . ? C13 C12 C17 N11 -19.7(12) . . . . ? C11 C12 C17 N11 161.0(8) . . . . ? O12 C18 N12 C11 0.6(12) . . . . ? C19 C18 N12 C11 -179.0(7) . . . . ? C16 C11 N12 C18 14.5(13) . . . . ? C12 C11 N12 C18 -168.6(7) . . . . ? C26 C21 C22 C23 6.6(11) . . . . ? N22 C21 C22 C23 -174.5(6) . . . . ? C26 C21 C22 C27 -172.1(7) . . . . ? N22 C21 C22 C27 6.8(11) . . . . ? C21 C22 C23 C24 -3.8(12) . . . . ? C27 C22 C23 C24 174.9(7) . . . . ? C22 C23 C24 C25 -1.1(14) . . . . ? C23 C24 C25 C26 3.1(15) . . . . ? C22 C21 C26 C25 -4.7(13) . . . . ? N22 C21 C26 C25 176.4(8) . . . . ? C24 C25 C26 C21 -0.3(14) . . . . ? C21 C22 C27 O21 -16.4(12) . . . . ? C23 C22 C27 O21 164.9(8) . . . . ? C21 C22 C27 N21 163.4(7) . . . . ? C23 C22 C27 N21 -15.3(12) . . . . ? O22 C28 N22 C21 2.0(13) . . . . ? C29 C28 N22 C21 -177.3(7) . . . . ? C22 C21 N22 C28 161.5(8) . . . . ? C26 C21 N22 C28 -19.6(12) . . . . ? N32 C31 C32 C33 178.8(7) . . . . ? C36 C31 C32 C33 -3.2(10) . . . . ? N32 C31 C32 C37 -0.8(11) . . . . ? C36 C31 C32 C37 177.3(6) . . . . ? C31 C32 C33 C34 1.6(12) . . . . ? C37 C32 C33 C34 -178.8(7) . . . . ? C32 C33 C34 C35 0.9(12) . . . . ? C33 C34 C35 C36 -1.9(12) . . . . ? C34 C35 C36 C31 0.3(12) . . . . ? N32 C31 C36 C35 -179.7(7) . . . . ? C32 C31 C36 C35 2.2(11) . . . . ? C33 C32 C37 O31 -175.7(7) . . . . ? C31 C32 C37 O31 3.9(11) . . . . ? C33 C32 C37 N31 4.3(11) . . . . ? C31 C32 C37 N31 -176.1(7) . . . . ? O32 C38 N32 C31 -4.7(13) . . . . ? C39 C38 N32 C31 178.5(7) . . . . ? C32 C31 N32 C38 -172.2(7) . . . . ? C36 C31 N32 C38 9.8(12) . . . . ? C46 C41 C42 C43 0.7(12) . . . . ? N42 C41 C42 C43 177.6(7) . . . . ? C46 C41 C42 C47 -178.5(7) . . . . ? N42 C41 C42 C47 -1.6(12) . . . . ? C41 C42 C43 C44 -0.1(12) . . . . ? C47 C42 C43 C44 179.2(7) . . . . ? C42 C43 C44 C45 -0.3(12) . . . . ? C43 C44 C45 C46 -0.1(13) . . . . ? C44 C45 C46 C41 0.8(14) . . . . ? N42 C41 C46 C45 -177.8(8) . . . . ? C42 C41 C46 C45 -1.1(13) . . . . ? C43 C42 C47 O41 -159.3(8) . . . . ? C41 C42 C47 O41 19.9(12) . . . . ? C43 C42 C47 N41 17.7(12) . . . . ? C41 C42 C47 N41 -163.1(8) . . . . ? O42 C48 N42 C41 -0.9(14) . . . . ? C49 C48 N42 C41 177.4(8) . . . . ? C46 C41 N42 C48 -9.3(14) . . . . ? C42 C41 N42 C48 174.0(8) . . . . ? C56 C51 C52 C53 0.5(11) . . . . ? N52 C51 C52 C53 -178.8(7) . . . . ? C56 C51 C52 C57 -177.0(7) . . . . ? N52 C51 C52 C57 3.8(11) . . . . ? C51 C52 C53 C54 0.2(12) . . . . ? C57 C52 C53 C54 177.7(8) . . . . ? C52 C53 C54 C55 -1.6(14) . . . . ? C53 C54 C55 C56 2.1(13) . . . . ? C52 C51 C56 C55 0.1(12) . . . . ? N52 C51 C56 C55 179.4(7) . . . . ? C54 C55 C56 C51 -1.5(12) . . . . ? C51 C52 C57 O51 -4.0(12) . . . . ? C53 C52 C57 O51 178.6(7) . . . . ? C51 C52 C57 N51 176.2(7) . . . . ? C53 C52 C57 N51 -1.2(11) . . . . ? O52 C58 N52 C51 -1.6(14) . . . . ? C59 C58 N52 C51 178.0(7) . . . . ? C56 C51 N52 C58 -2.8(12) . . . . ? C52 C51 N52 C58 176.5(8) . . . . ? C6S O1S C2S C3S 19(3) . . . . ? O1S C2S C3S O4S -31(2) . . . . ? C2S C3S O4S C5S 52.1(18) . . . . ? C3S O4S C5S C6S -64.2(15) . . . . ? C2S O1S C6S C5S -30(2) . . . . ? O4S C5S C6S O1S 55.2(17) . . . . ? C16S O11S C12S C13S 75(2) . . . . ? O11S C12S C13S O14S -65(2) . . . . ? C12S C13S O14S C15S 31(4) . . . . ? C13S O14S C15S C16S 4(4) . . . . ? O14S C15S C16S O11S 6(3) . . . . ? C12S O11S C16S C15S -53(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A O31 0.88 2.09 2.964(7) 176.1 . N1 H1B O52 0.88 2.15 3.002(9) 163.9 1_445 C3 H3A O52 0.95 2.39 3.336(11) 172.0 1_445 N11 H11A O41 0.88 2.05 2.929(8) 177.0 2_666 N11 H11B O2 0.88 2.05 2.896(9) 161.7 1_556 C13 H13A O2 0.95 2.45 3.188(8) 134.8 1_556 N21 H21A O51 0.88 2.06 2.944(9) 177.2 . N21 H21B O12 0.88 2.12 2.975(7) 164.6 1_655 C23 H23A O12 0.95 2.48 3.308(9) 145.2 1_655 N31 H31A O1 0.88 2.10 2.979(7) 172.3 . N31 H31B O22 0.88 2.09 2.951(9) 165.4 . C33 H33A O22 0.95 2.34 3.270(10) 167.4 . N41 H41A O11 0.88 2.10 2.976(8) 175.3 2_666 N41 H41B O32 0.88 2.07 2.929(8) 163.8 2_656 C43 H43A O32 0.95 2.53 3.309(7) 139.6 2_656 N51 H51A O21 0.88 2.04 2.925(9) 179.3 . N51 H51B O42 0.88 2.13 2.987(7) 163.2 2_665 C53 H53A O42 0.95 2.35 3.300(10) 174.4 2_665 N2 H2A O1 0.88 1.97 2.645(7) 132.9 . N12 H12A O11 0.88 1.93 2.657(7) 139.1 . N22 H22A O21 0.88 1.97 2.635(9) 131.5 . N32 H32A O31 0.88 1.93 2.654(7) 138.3 . N42 H42A O41 0.88 1.90 2.630(6) 139.6 . N52 H52A O51 0.88 1.89 2.628(9) 140.3 . _diffrn_measured_fraction_theta_max 0.714 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.874 _refine_diff_density_max 0.810 _refine_diff_density_min -0.777 _refine_diff_density_rms 0.150