# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Louis Cuccia' _publ_contact_author_address ; Chemistry & Biochemistry Concordia University 7141 Sherbrooke Street West Montreal Quebec H4B 1R6 CANADA ; _publ_contact_author_email CUCCIAL@ALCOR.CONCORDIA.CA _publ_section_title ; Hydrogen Bond Directed Synthesis of Pyridazine and Naphthyridine Containing Macrocycles ; loop_ _publ_author_name 'Louis Cuccia' 'Todd C. Sutherland' 'Liyan Xing' 'Ulrich Ziener' data_cuccia1 _database_code_depnum_ccdc_archive 'CCDC 267802' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H18 N12,1.50(C2 H6 O S),(C H4 O)' _chemical_formula_sum 'C31 H31 N12 O2.50 S1.50' _chemical_formula_weight 659.77 _chemical_compound_source 'Synthesized by the authors. See text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbcn _symmetry_space_group_name_hall '-P 2n 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 31.1325(6) _cell_length_b 8.5333(2) _cell_length_c 22.9610(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 6099.9(2) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7455 _cell_measurement_theta_min 2.84 _cell_measurement_theta_max 71.51 _exptl_crystal_description needle-like _exptl_crystal_colour yellow _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.437 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2760 _exptl_absorpt_coefficient_mu 1.718 _exptl_absorpt_correction_Type multi-scan _exptl_absorpt_correction_T_min 0.6800 _exptl_absorpt_correction_T_max 0.9500 _exptl_absorpt_process_details 'Sadabs (Sheldrick,1996)' _exptl_special_details ; X-ray crystallographic data for I were collected from a single crystal sample, which was mounted on a loop fiber. Data were collected using a Bruker Platform diffractometer, equipped with a Bruker SMART 2K Charged-Coupled Device (CCD) Area Detector using the program SMART and normal focus sealed tube source graphite monochromated Cu-K\a radiation. The crystal-to-detector distance was 4.908 cm, and the data collection was carried out in 512 x 512 pixel mode, utilizing 4 x 4 pixel binning. The initial unit cell parameters were determined by a least-squares fit of the angular setting of strong reflections, collected by a 9.0 degree scan in 30 frames over four different parts of the reciprocal space (120 frames total). One complete sphere of data was collected, to better than 0.8\%A resolution. Upon completion of the data collection, the first 101 frames were recollected in order to improve the decay correction analysis. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Sealed Tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS Smart 2K/Platform' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 5.5 _diffrn_standards_number 249 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 57006 _diffrn_reflns_av_R_equivalents 0.044 _diffrn_reflns_av_sigmaI/netI 0.0856 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.84 _diffrn_reflns_theta_max 55.04 _reflns_number_total 3816 _reflns_number_gt 2282 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 1999)' _computing_cell_refinement 'SMART (Bruker, 1999)' _computing_data_reduction 'SAINT (Bruker, 1999)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material 'UdMX (local program)' _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^)+(0.0181P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3816 _refine_ls_number_parameters 448 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0846 _refine_ls_R_factor_gt 0.0394 _refine_ls_wR_factor_ref 0.0687 _refine_ls_wR_factor_gt 0.0629 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.004 _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 0.38410(11) 0.0603(4) 0.54081(13) 0.0253(9) Uani 1 1 d . . . H1 H 0.3793 0.1254 0.5079 0.030 Uiso 1 1 calc R . . N2 N 0.35104(8) -0.0204(3) 0.56395(10) 0.0244(7) Uani 1 1 d . . . H2 H 0.3570 -0.0902 0.5910 0.037 Uiso 1 1 calc R . . C3 C 0.30784(11) -0.0013(4) 0.54820(14) 0.0231(9) Uani 1 1 d . . . C4 C 0.27661(11) -0.0860(4) 0.58021(13) 0.0258(9) Uani 1 1 d . . . H4 H 0.2847 -0.1526 0.6115 0.031 Uiso 1 1 calc R . . C5 C 0.23485(11) -0.0694(4) 0.56496(13) 0.0277(9) Uani 1 1 d . . . H5 H 0.2131 -0.1249 0.5854 0.033 Uiso 1 1 calc R . . C6 C 0.22374(11) 0.0312(4) 0.51827(13) 0.0226(8) Uani 1 1 d . . . C7 C 0.18139(10) 0.0539(4) 0.49801(14) 0.0296(9) Uani 1 1 d . . . H7 H 0.1583 -0.0035 0.5145 0.036 Uiso 1 1 calc R . . C8 C 0.17403(10) 0.1593(4) 0.45444(14) 0.0281(9) Uani 1 1 d . . . H8 H 0.1457 0.1773 0.4405 0.034 Uiso 1 1 calc R . . C9 C 0.20948(11) 0.2415(4) 0.43042(13) 0.0226(9) Uani 1 1 d . . . N10 N 0.24978(8) 0.2183(3) 0.44664(10) 0.0225(7) Uani 1 1 d . . . C11 C 0.25720(11) 0.1131(4) 0.49010(13) 0.0202(8) Uani 1 1 d . . . N12 N 0.29939(9) 0.0965(3) 0.50522(10) 0.0234(7) Uani 1 1 d . . . N13 N 0.19923(8) 0.3542(3) 0.38766(11) 0.0251(7) Uani 1 1 d . . . C14 C 0.23122(11) 0.4185(4) 0.36134(13) 0.0239(9) Uani 1 1 d . . . H14 H 0.2597 0.3898 0.3719 0.029 Uiso 1 1 calc R . . N15 N 0.22502(8) 0.5265(3) 0.31882(10) 0.0236(7) Uani 1 1 d . . . H15 H 0.1984 0.5546 0.3110 0.035 Uiso 1 1 calc R . . C16 C 0.25772(12) 0.5957(4) 0.28693(13) 0.0219(8) Uani 1 1 d . . . C17 C 0.24493(11) 0.6987(4) 0.24112(12) 0.0265(9) Uani 1 1 d . . . H17 H 0.2155 0.7185 0.2334 0.032 Uiso 1 1 calc R . . C18 C 0.27616(11) 0.7667(4) 0.20924(13) 0.0258(9) Uani 1 1 d . . . H18 H 0.2688 0.8349 0.1781 0.031 Uiso 1 1 calc R . . C19 C 0.31946(11) 0.7371(4) 0.22190(13) 0.0231(8) Uani 1 1 d . . . C20 C 0.35431(12) 0.7990(4) 0.19077(13) 0.0320(9) Uani 1 1 d . . . H20 H 0.3491 0.8668 0.1587 0.038 Uiso 1 1 calc R . . C21 C 0.39514(11) 0.7634(4) 0.20577(13) 0.0361(10) Uani 1 1 d . . . H21 H 0.4189 0.8030 0.1844 0.043 Uiso 1 1 calc R . . C22 C 0.40088(12) 0.6643(4) 0.25476(14) 0.0359(10) Uani 1 1 d . . . N23 N 0.36967(9) 0.6008(3) 0.28528(10) 0.0284(8) Uani 1 1 d . . . C24 C 0.32897(12) 0.6352(4) 0.26940(13) 0.0234(9) Uani 1 1 d . . . N25 N 0.29773(9) 0.5634(3) 0.30084(10) 0.0226(7) Uani 1 1 d . . . N26 N 0.44279(9) 0.6297(4) 0.27052(12) 0.0644(11) Uani 1 1 d . . . H26 H 0.4634 0.6566 0.2463 0.097 Uiso 1 1 calc R . . C27 C 0.45415(11) 0.5575(4) 0.32066(15) 0.0378(10) Uani 1 1 d . . . H27 H 0.4325 0.5235 0.3469 0.045 Uiso 1 1 calc R . . N28 N 0.49384(9) 0.5342(4) 0.33338(12) 0.0501(9) Uani 1 1 d . . . C29 C 0.50142(11) 0.4542(4) 0.38621(15) 0.0335(9) Uani 1 1 d . . . C30 C 0.54346(10) 0.4694(4) 0.40934(14) 0.0346(10) Uani 1 1 d . . . H30 H 0.5643 0.5320 0.3901 0.042 Uiso 1 1 calc R . . C31 C 0.55336(10) 0.3924(4) 0.45962(15) 0.0353(10) Uani 1 1 d . . . H31 H 0.5814 0.4001 0.4758 0.042 Uiso 1 1 calc R . . C32 C 0.52173(11) 0.3018(4) 0.48717(14) 0.0276(9) Uani 1 1 d . . . C33 C 0.52785(11) 0.2211(4) 0.54007(15) 0.0387(10) Uani 1 1 d . . . H33 H 0.5550 0.2246 0.5590 0.046 Uiso 1 1 calc R . . C34 C 0.49490(11) 0.1380(4) 0.56406(14) 0.0388(10) Uani 1 1 d . . . H34 H 0.4989 0.0822 0.5994 0.047 Uiso 1 1 calc R . . C35 C 0.45486(11) 0.1361(4) 0.53568(15) 0.0265(9) Uani 1 1 d . . . N36 N 0.44766(8) 0.2115(3) 0.48577(11) 0.0266(7) Uani 1 1 d . . . C37 C 0.48071(11) 0.2934(4) 0.46191(14) 0.0256(8) Uani 1 1 d . . . N38 N 0.47104(8) 0.3691(3) 0.41080(11) 0.0322(8) Uani 1 1 d . . . N39 N 0.42211(9) 0.0503(3) 0.56279(10) 0.0277(7) Uani 1 1 d . . . C41 C 0.64472(11) 0.3618(4) 0.33921(13) 0.0464(11) Uani 1 1 d . . . H41A H 0.6445 0.3878 0.3808 0.070 Uiso 1 1 calc R . . H41B H 0.6203 0.4126 0.3200 0.070 Uiso 1 1 calc R . . H41C H 0.6716 0.3988 0.3217 0.070 Uiso 1 1 calc R . . O41 O 0.64152(7) 0.1979(3) 0.33230(8) 0.0347(6) Uani 1 1 d . . . H41 H 0.6385 0.1763 0.2968 0.052 Uiso 1 1 calc R . . S50 S 0.61095(3) 0.19301(10) 0.17181(3) 0.0272(2) Uani 1 1 d D . . O51 O 0.64359(6) 0.1384(2) 0.21718(8) 0.0302(6) Uani 1 1 d D . . C52 C 0.64098(9) 0.2889(4) 0.11634(12) 0.0307(9) Uani 1 1 d D . . H52A H 0.6544 0.3833 0.1324 0.046 Uiso 1 1 calc R . . H52B H 0.6218 0.3182 0.0843 0.046 Uiso 1 1 calc R . . H52C H 0.6633 0.2180 0.1017 0.046 Uiso 1 1 calc R . . C53 C 0.59683(9) 0.0197(3) 0.13265(12) 0.0347(9) Uani 1 1 d D . . H53A H 0.6230 -0.0351 0.1205 0.052 Uiso 1 1 calc R . . H53B H 0.5800 0.0481 0.0982 0.052 Uiso 1 1 calc R . . H53C H 0.5797 -0.0491 0.1578 0.052 Uiso 1 1 calc R . . S60 S 0.51331(6) 0.0344(3) 0.23756(10) 0.0490(6) Uani 0.50 1 d PD A -1 O61 O 0.4971(4) -0.1127(5) 0.2675(3) 0.050(2) Uani 0.50 1 d PD A -1 C62 C 0.4670(8) 0.131(3) 0.2077(12) 0.065(9) Uani 0.50 1 d PD A -1 H62A H 0.4577 0.0765 0.1724 0.097 Uiso 0.50 1 calc PR A -1 H62B H 0.4744 0.2399 0.1980 0.097 Uiso 0.50 1 calc PR A -1 H62C H 0.4437 0.1306 0.2364 0.097 Uiso 0.50 1 calc PR A -1 C63 C 0.5243(8) 0.169(3) 0.2964(11) 0.051(6) Uani 0.50 1 d PD A -1 H63A H 0.4985 0.1815 0.3204 0.077 Uiso 0.50 1 calc PR A -1 H63B H 0.5326 0.2713 0.2803 0.077 Uiso 0.50 1 calc PR A -1 H63C H 0.5478 0.1282 0.3204 0.077 Uiso 0.50 1 calc PR A -1 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 0.035(3) 0.030(2) 0.010(2) -0.0005(17) 0.005(2) -0.001(2) N2 0.0305(19) 0.0274(19) 0.0153(16) 0.0060(13) -0.0017(15) 0.0016(15) C3 0.031(3) 0.022(2) 0.016(2) -0.0091(18) 0.0039(19) 0.0032(19) C4 0.037(3) 0.028(2) 0.013(2) -0.0011(16) 0.0005(19) -0.0010(19) C5 0.040(3) 0.027(2) 0.017(2) -0.0030(18) 0.0068(19) -0.0062(19) C6 0.029(2) 0.024(2) 0.015(2) -0.0045(18) 0.0037(18) -0.0007(19) C7 0.030(3) 0.032(3) 0.027(2) -0.0031(19) 0.0040(19) -0.0042(19) C8 0.024(2) 0.035(3) 0.026(2) -0.0033(19) -0.0010(18) 0.0008(19) C9 0.033(2) 0.021(2) 0.013(2) -0.0059(17) 0.002(2) 0.0015(19) N10 0.0273(18) 0.0252(19) 0.0151(16) 0.0019(14) -0.0003(14) 0.0050(14) C11 0.028(2) 0.020(2) 0.013(2) -0.0053(17) -0.0004(19) 0.0012(18) N12 0.031(2) 0.0262(19) 0.0130(17) 0.0017(13) -0.0029(14) 0.0046(14) N13 0.0298(19) 0.028(2) 0.0173(17) -0.0001(15) 0.0011(15) -0.0023(15) C14 0.030(3) 0.026(2) 0.016(2) -0.0055(18) -0.0068(18) 0.0080(19) N15 0.0237(18) 0.0282(19) 0.0188(17) 0.0003(15) -0.0030(14) 0.0069(14) C16 0.033(3) 0.020(2) 0.012(2) -0.0048(17) 0.0041(19) -0.0008(19) C17 0.032(2) 0.027(2) 0.020(2) -0.0013(19) -0.0058(19) 0.0088(19) C18 0.036(3) 0.026(2) 0.014(2) -0.0001(17) -0.0016(19) 0.0034(19) C19 0.030(2) 0.024(2) 0.016(2) 0.0002(17) 0.0000(19) -0.0031(18) C20 0.045(3) 0.031(2) 0.019(2) 0.0023(17) -0.006(2) -0.007(2) C21 0.037(3) 0.052(3) 0.019(2) 0.0106(19) 0.0011(19) -0.011(2) C22 0.028(3) 0.057(3) 0.022(2) 0.005(2) -0.007(2) -0.006(2) N23 0.024(2) 0.044(2) 0.0170(18) 0.0038(14) -0.0010(15) -0.0026(15) C24 0.032(3) 0.026(2) 0.012(2) -0.0068(17) 0.0036(19) -0.004(2) N25 0.0226(18) 0.030(2) 0.0148(17) -0.0017(13) 0.0006(15) 0.0036(15) N26 0.029(2) 0.132(3) 0.032(2) 0.047(2) -0.0019(17) -0.014(2) C27 0.037(3) 0.054(3) 0.022(2) 0.009(2) 0.003(2) -0.010(2) N28 0.027(2) 0.097(3) 0.0267(19) 0.0283(19) -0.0055(16) -0.0043(18) C29 0.026(3) 0.050(3) 0.025(2) 0.000(2) 0.001(2) 0.002(2) C30 0.022(2) 0.050(3) 0.032(2) 0.005(2) 0.0043(19) 0.0014(19) C31 0.025(2) 0.040(3) 0.040(3) 0.001(2) -0.008(2) 0.003(2) C32 0.025(2) 0.032(2) 0.026(2) 0.0026(19) -0.0044(19) 0.000(2) C33 0.032(3) 0.042(3) 0.042(3) 0.008(2) -0.014(2) 0.001(2) C34 0.035(3) 0.047(3) 0.035(2) 0.0130(19) -0.014(2) -0.002(2) C35 0.030(3) 0.025(2) 0.024(2) -0.0041(18) 0.000(2) 0.0029(19) N36 0.0312(19) 0.0323(19) 0.0163(17) -0.0005(15) 0.0001(15) -0.0021(15) C37 0.026(2) 0.029(2) 0.022(2) -0.0046(19) 0.0023(19) 0.002(2) N38 0.030(2) 0.049(2) 0.0181(18) 0.0087(16) 0.0011(15) -0.0045(16) N39 0.0289(19) 0.035(2) 0.0189(17) -0.0005(14) -0.0040(16) -0.0016(16) C41 0.068(3) 0.040(3) 0.030(2) -0.004(2) 0.008(2) 0.013(2) O41 0.0554(16) 0.0339(17) 0.0148(13) 0.0005(12) -0.0059(13) 0.0019(13) S50 0.0272(5) 0.0364(6) 0.0181(5) -0.0007(4) -0.0002(5) 0.0023(5) O51 0.0292(14) 0.0449(16) 0.0163(13) -0.0027(11) -0.0079(11) 0.0110(11) C52 0.033(2) 0.039(2) 0.021(2) 0.0031(17) 0.0013(17) -0.0067(18) C53 0.040(2) 0.033(2) 0.031(2) -0.0009(18) -0.0082(17) -0.0016(18) S60 0.0450(19) 0.0515(15) 0.0504(18) -0.0032(13) 0.0162(12) -0.0021(11) O61 0.056(4) 0.023(3) 0.070(7) -0.002(3) 0.009(6) 0.017(4) C62 0.078(13) 0.069(17) 0.048(9) 0.037(10) 0.019(8) 0.027(13) C63 0.079(12) 0.040(9) 0.035(10) 0.003(8) 0.005(8) -0.008(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_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 N39 . . 1.289(3) Y C1 N2 . . 1.347(3) Y C1 H1 . . 0.95 ? N2 C3 . . 1.402(3) Y N2 H2 . . 0.88 ? C3 N12 . . 1.319(3) Y C3 C4 . . 1.417(4) Y C4 C5 . . 1.354(4) Y C4 H4 . . 0.95 ? C5 C6 . . 1.416(4) Y C5 H5 . . 0.95 ? C6 C7 . . 1.411(4) Y C6 C11 . . 1.412(4) Y C7 C8 . . 1.364(4) Y C7 H7 . . 0.95 ? C8 C9 . . 1.419(4) Y C8 H8 . . 0.95 ? C9 N10 . . 1.324(3) Y C9 N13 . . 1.411(3) Y N10 C11 . . 1.362(3) Y C11 N12 . . 1.366(3) Y N13 C14 . . 1.288(3) Y C14 N15 . . 1.357(3) Y C14 H14 . . 0.95 ? N15 C16 . . 1.386(3) Y N15 H15 . . 0.88 ? C16 N25 . . 1.315(3) Y C16 C17 . . 1.427(4) Y C17 C18 . . 1.349(4) Y C17 H17 . . 0.95 ? C18 C19 . . 1.402(4) Y C18 H18 . . 0.95 ? C19 C20 . . 1.402(4) Y C19 C24 . . 1.426(4) Y C20 C21 . . 1.352(4) Y C20 H20 . . 0.95 ? C21 C22 . . 1.418(4) Y C21 H21 . . 0.95 ? C22 N23 . . 1.315(4) Y C22 N26 . . 1.386(4) Y N23 C24 . . 1.351(3) Y C24 N25 . . 1.357(3) Y N26 C27 . . 1.353(4) Y N26 H26 . . 0.88 ? C27 N28 . . 1.285(3) Y C27 H27 . . 0.95 ? N28 C29 . . 1.412(4) Y C29 N38 . . 1.319(4) Y C29 C30 . . 1.418(4) Y C30 C31 . . 1.363(4) Y C30 H30 . . 0.95 ? C31 C32 . . 1.403(4) Y C31 H31 . . 0.95 ? C32 C37 . . 1.404(4) Y C32 C33 . . 1.409(4) Y C33 C34 . . 1.363(4) Y C33 H33 . . 0.95 ? C34 C35 . . 1.407(4) Y C34 H34 . . 0.95 ? C35 N36 . . 1.333(4) Y C35 N39 . . 1.401(4) Y N36 C37 . . 1.359(3) Y C37 N38 . . 1.373(4) Y C41 O41 . . 1.411(3) Y C41 H41a . . 0.98 ? C41 H41b . . 0.98 ? C41 H41c . . 0.98 ? O41 H41 . . 0.84 ? S50 O51 . . 1.5282(18) Y S50 C52 . . 1.779(3) Y S50 C53 . . 1.786(3) Y C52 H52a . . 0.98 ? C52 H52b . . 0.98 ? C52 H52c . . 0.98 ? C53 H53a . . 0.98 ? C53 H53b . . 0.98 ? C53 H53c . . 0.98 ? S60 O61 . . 1.518(5) Y S60 C62 . . 1.798(16) Y S60 C63 . . 1.808(16) Y C62 H62a . . 0.98 ? C62 H62b . . 0.98 ? C62 H62c . . 0.98 ? C63 H63a . . 0.98 ? C63 H63b . . 0.98 ? C63 H63c . . 0.98 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag N39 C1 N2 . . . 120.9(3) Y N39 C1 H1 . . . 119.6 ? N2 C1 H1 . . . 119.6 ? C1 N2 C3 . . . 124.9(3) Y C1 N2 H2 . . . 117.6 ? C3 N2 H2 . . . 117.6 ? N12 C3 N2 . . . 117.2(3) Y N12 C3 C4 . . . 125.0(3) Y N2 C3 C4 . . . 117.7(3) Y C5 C4 C3 . . . 118.1(3) Y C5 C4 H4 . . . 120.9 ? C3 C4 H4 . . . 120.9 ? C4 C5 C6 . . . 119.6(3) Y C4 C5 H5 . . . 120.2 ? C6 C5 H5 . . . 120.2 ? C7 C6 C11 . . . 118.0(3) Y C7 C6 C5 . . . 124.1(3) Y C11 C6 C5 . . . 117.8(3) Y C8 C7 C6 . . . 119.3(3) Y C8 C7 H7 . . . 120.4 ? C6 C7 H7 . . . 120.4 ? C7 C8 C9 . . . 118.7(3) Y C7 C8 H8 . . . 120.7 ? C9 C8 H8 . . . 120.7 ? N10 C9 N13 . . . 120.8(3) Y N10 C9 C8 . . . 123.6(3) Y N13 C9 C8 . . . 115.6(3) Y C9 N10 C11 . . . 117.7(3) Y N10 C11 N12 . . . 114.7(3) Y N10 C11 C6 . . . 122.5(3) Y N12 C11 C6 . . . 122.8(3) Y C3 N12 C11 . . . 116.6(3) Y C14 N13 C9 . . . 116.3(3) Y N13 C14 N15 . . . 121.2(3) Y N13 C14 H14 . . . 119.4 ? N15 C14 H14 . . . 119.4 ? C14 N15 C16 . . . 124.4(3) Y C14 N15 H15 . . . 117.8 ? C16 N15 H15 . . . 117.8 ? N25 C16 N15 . . . 118.6(3) Y N25 C16 C17 . . . 124.9(3) Y N15 C16 C17 . . . 116.5(3) Y C18 C17 C16 . . . 117.6(3) Y C18 C17 H17 . . . 121.2 ? C16 C17 H17 . . . 121.2 ? C17 C18 C19 . . . 120.2(3) Y C17 C18 H18 . . . 119.9 ? C19 C18 H18 . . . 119.9 ? C18 C19 C20 . . . 124.8(3) Y C18 C19 C24 . . . 117.9(3) Y C20 C19 C24 . . . 117.3(3) Y C21 C20 C19 . . . 120.9(3) Y C21 C20 H20 . . . 119.6 ? C19 C20 H20 . . . 119.6 ? C20 C21 C22 . . . 117.0(3) Y C20 C21 H21 . . . 121.5 ? C22 C21 H21 . . . 121.5 ? N23 C22 N26 . . . 117.9(3) Y N23 C22 C21 . . . 125.1(3) Y N26 C22 C21 . . . 116.9(3) Y C22 N23 C24 . . . 117.4(3) Y N23 C24 N25 . . . 115.5(3) Y N23 C24 C19 . . . 122.3(3) Y N25 C24 C19 . . . 122.2(3) Y C16 N25 C24 . . . 117.1(3) Y C27 N26 C22 . . . 124.4(3) Y C27 N26 H26 . . . 117.8 ? C22 N26 H26 . . . 117.8 ? N28 C27 N26 . . . 121.0(3) Y N28 C27 H27 . . . 119.5 ? N26 C27 H27 . . . 119.5 ? C27 N28 C29 . . . 115.5(3) Y N38 C29 N28 . . . 120.9(3) Y N38 C29 C30 . . . 123.5(3) Y N28 C29 C30 . . . 115.6(3) Y C31 C30 C29 . . . 118.8(3) Y C31 C30 H30 . . . 120.6 ? C29 C30 H30 . . . 120.6 ? C30 C31 C32 . . . 119.3(3) Y C30 C31 H31 . . . 120.4 ? C32 C31 H31 . . . 120.4 ? C31 C32 C37 . . . 118.7(3) Y C31 C32 C33 . . . 124.3(3) Y C37 C32 C33 . . . 117.0(3) Y C34 C33 C32 . . . 120.0(3) Y C34 C33 H33 . . . 120 ? C32 C33 H33 . . . 120 ? C33 C34 C35 . . . 119.1(3) Y C33 C34 H34 . . . 120.5 ? C35 C34 H34 . . . 120.5 ? N36 C35 N39 . . . 120.8(3) Y N36 C35 C34 . . . 122.8(3) Y N39 C35 C34 . . . 116.4(3) Y C35 N36 C37 . . . 117.9(3) Y N36 C37 N38 . . . 114.9(3) Y N36 C37 C32 . . . 123.2(3) Y N38 C37 C32 . . . 121.9(3) Y C29 N38 C37 . . . 117.9(3) Y C1 N39 C35 . . . 117.4(3) Y O41 C41 H41A . . . 109.5 ? O41 C41 H41B . . . 109.5 ? H41A C41 H41B . . . 109.5 ? O41 C41 H41C . . . 109.5 ? H41A C41 H41C . . . 109.5 ? H41B C41 H41C . . . 109.5 ? C41 O41 H41 . . . 109.5 ? O51 S50 C52 . . . 106.19(12) Y O51 S50 C53 . . . 104.73(13) Y C52 S50 C53 . . . 98.61(14) Y S50 C52 H52A . . . 109.5 ? S50 C52 H52B . . . 109.5 ? H52A C52 H52B . . . 109.5 ? S50 C52 H52C . . . 109.5 ? H52A C52 H52C . . . 109.5 ? H52B C52 H52C . . . 109.5 ? S50 C53 H53A . . . 109.5 ? S50 C53 H53B . . . 109.5 ? H53A C53 H53B . . . 109.5 ? S50 C53 H53C . . . 109.5 ? H53A C53 H53C . . . 109.5 ? H53B C53 H53C . . . 109.5 ? O61 S60 C62 . . . 106.6(1) Y O61 S60 C63 . . . 104.5(9) Y C62 S60 C63 . . . 98.3(8) Y 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag N39 C1 N2 C3 . . . . 171.1(3) ? C1 N2 C3 N12 . . . . 4.1(4) ? C1 N2 C3 C4 . . . . -174.8(3) ? N12 C3 C4 C5 . . . . 1.8(5) ? N2 C3 C4 C5 . . . . -179.4(3) ? C3 C4 C5 C6 . . . . -0.2(4) ? C4 C5 C6 C7 . . . . 178.4(3) ? C4 C5 C6 C11 . . . . -1.2(4) ? C11 C6 C7 C8 . . . . -3.4(4) ? C5 C6 C7 C8 . . . . 177.0(3) ? C6 C7 C8 C9 . . . . 0.7(4) ? C7 C8 C9 N10 . . . . 2.2(5) ? C7 C8 C9 N13 . . . . -176.9(3) ? N13 C9 N10 C11 . . . . 176.9(3) ? C8 C9 N10 C11 . . . . -2.2(4) ? C9 N10 C11 N12 . . . . -179.1(2) ? C9 N10 C11 C6 . . . . -0.8(4) ? C7 C6 C11 N10 . . . . 3.6(4) ? C5 C6 C11 N10 . . . . -176.8(3) ? C7 C6 C11 N12 . . . . -178.2(3) ? C5 C6 C11 N12 . . . . 1.4(4) ? N2 C3 N12 C11 . . . . 179.6(2) ? C4 C3 N12 C11 . . . . -1.6(4) ? N10 C11 N12 C3 . . . . 178.3(2) ? C6 C11 N12 C3 . . . . 0.0(4) ? N10 C9 N13 C14 . . . . 7.5(4) ? C8 C9 N13 C14 . . . . -173.3(3) ? C9 N13 C14 N15 . . . . 178.9(3) ? N13 C14 N15 C16 . . . . -177.1(3) ? C14 N15 C16 N25 . . . . -4.7(4) ? C14 N15 C16 C17 . . . . 175.7(3) ? N25 C16 C17 C18 . . . . 0.8(5) ? N15 C16 C17 C18 . . . . -179.7(3) ? C16 C17 C18 C19 . . . . -0.8(4) ? C17 C18 C19 C20 . . . . 178.5(3) ? C17 C18 C19 C24 . . . . -0.6(4) ? C18 C19 C20 C21 . . . . -179.6(3) ? C24 C19 C20 C21 . . . . -0.4(4) ? C19 C20 C21 C22 . . . . -1.3(5) ? C20 C21 C22 N23 . . . . 2.4(5) ? C20 C21 C22 N26 . . . . -179.2(3) ? N26 C22 N23 C24 . . . . -179.9(3) ? C21 C22 N23 C24 . . . . -1.4(5) ? C22 N23 C24 N25 . . . . 178.0(3) ? C22 N23 C24 C19 . . . . -0.5(4) ? C18 C19 C24 N23 . . . . -179.4(3) ? C20 C19 C24 N23 . . . . 1.4(4) ? C18 C19 C24 N25 . . . . 2.2(4) ? C20 C19 C24 N25 . . . . -177.0(3) ? N15 C16 N25 C24 . . . . -178.9(2) ? C17 C16 N25 C24 . . . . 0.7(4) ? N23 C24 N25 C16 . . . . 179.3(3) ? C19 C24 N25 C16 . . . . -2.2(4) ? N23 C22 N26 C27 . . . . -11.8(5) ? C21 C22 N26 C27 . . . . 169.6(3) ? C22 N26 C27 N28 . . . . -177.5(3) ? N26 C27 N28 C29 . . . . -178.5(3) ? C27 N28 C29 N38 . . . . 19.8(5) ? C27 N28 C29 C30 . . . . -161.6(3) ? N38 C29 C30 C31 . . . . 0.0(5) ? N28 C29 C30 C31 . . . . -178.6(3) ? C29 C30 C31 C32 . . . . -0.5(5) ? C30 C31 C32 C37 . . . . 0.0(5) ? C30 C31 C32 C33 . . . . -178.0(3) ? C31 C32 C33 C34 . . . . 178.9(3) ? C37 C32 C33 C34 . . . . 0.8(5) ? C32 C33 C34 C35 . . . . -0.9(5) ? C33 C34 C35 N36 . . . . 0.5(5) ? C33 C34 C35 N39 . . . . -179.2(3) ? N39 C35 N36 C37 . . . . 179.6(3) ? C34 C35 N36 C37 . . . . -0.1(4) ? C35 N36 C37 N38 . . . . -179.5(3) ? C35 N36 C37 C32 . . . . 0.1(4) ? C31 C32 C37 N36 . . . . -178.6(3) ? C33 C32 C37 N36 . . . . -0.5(5) ? C31 C32 C37 N38 . . . . 1.0(5) ? C33 C32 C37 N38 . . . . 179.2(3) ? N28 C29 N38 C37 . . . . 179.5(3) ? C30 C29 N38 C37 . . . . 0.9(5) ? N36 C37 N38 C29 . . . . 178.2(3) ? C32 C37 N38 C29 . . . . -1.5(5) ? N2 C1 N39 C35 . . . . 179.1(3) ? N36 C35 N39 C1 . . . . -6.8(4) ? C34 C35 N39 C1 . . . . 173.0(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 O41 0.88 1.99 2.832(3) 160.5 5_656 N15 H15 O51 0.88 1.96 2.832(3) 170.3 6_566 N26 H26 O61 0.88 2.28 2.773(9) 115.1 1_565 N26 H26 O61 0.88 2.34 3.017(8) 133.4 3_665 O41 H41 O51 0.84 1.86 2.692(3) 168.5 . N10 H14 N25 2.277 2.502 4.702(4) 159.42 . N23 H27 N38 2.501 2.309 4.709(4) 156.40 . N36 H1 N12 2.307 2.502 4.740(4) 160.61 . _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 55.04 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.196 _refine_diff_density_min -0.277 _refine_diff_density_rms 0.047 data_z1a _database_code_depnum_ccdc_archive 'CCDC 267803' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21.33 H28.33 Cl N6 O2' _chemical_formula_weight 436.28 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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' _cell_length_a 20.888(4) _cell_length_b 20.888(4) _cell_length_c 8.774(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 3315.2(17) _cell_formula_units_Z 6 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.311 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1388 _exptl_absorpt_coefficient_mu 0.203 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16251 _diffrn_reflns_av_R_equivalents 0.0744 _diffrn_reflns_av_sigmaI/netI 0.0734 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.98 _diffrn_reflns_theta_max 26.97 _reflns_number_total 4348 _reflns_number_gt 2748 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0612P)^2^+1.8137P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0000(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4348 _refine_ls_number_parameters 285 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0953 _refine_ls_R_factor_gt 0.0493 _refine_ls_wR_factor_ref 0.1420 _refine_ls_wR_factor_gt 0.1164 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _refine_ls_shift/su_max 3.459 _refine_ls_shift/su_mean 0.012 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 Cl1 Cl 0.72536(5) 0.42404(5) 0.80286(10) 0.0481(3) Uani 1 1 d . . . O1 O 0.58232(11) 0.39167(10) 0.4519(2) 0.0300(5) Uani 1 1 d . . . O2 O 0.76921(10) 0.80759(10) 1.1265(2) 0.0221(4) Uani 1 1 d . . . N1 N 0.54815(12) 0.44913(12) 0.6261(3) 0.0200(5) Uani 1 1 d . . . N2 N 0.67077(11) 0.50590(12) 0.5311(2) 0.0186(5) Uani 1 1 d . . . N3 N 0.65730(11) 0.57110(11) 0.7352(2) 0.0183(5) Uani 1 1 d . . . N4 N 0.68245(11) 0.63119(11) 0.8264(2) 0.0185(5) Uani 1 1 d . . . N5 N 0.77395(11) 0.74862(11) 0.9109(2) 0.0170(5) Uani 1 1 d . . . N6 N 0.67717(12) 0.68939(12) 1.0872(2) 0.0194(5) Uani 1 1 d . . . C1 C 0.87517(16) 0.92737(16) 0.6812(3) 0.0308(7) Uani 1 1 d . . . H1A H 0.9197 0.9244 0.6597 0.046 Uiso 1 1 calc R . . H1B H 0.8846 0.9609 0.7672 0.046 Uiso 1 1 calc R . . H1C H 0.8621 0.9461 0.5910 0.046 Uiso 1 1 calc R . . C2 C 0.81165(14) 0.85074(15) 0.7209(3) 0.0215(6) Uani 1 1 d . . . H2A H 0.8021 0.8176 0.6312 0.026 Uiso 1 1 calc R . . C3 C 0.74154(16) 0.85366(16) 0.7542(3) 0.0279(7) Uani 1 1 d . . . H3A H 0.7013 0.8040 0.7793 0.042 Uiso 1 1 calc R . . H3B H 0.7280 0.8721 0.6643 0.042 Uiso 1 1 calc R . . H3C H 0.7503 0.8868 0.8406 0.042 Uiso 1 1 calc R . . C4 C 0.83419(13) 0.82029(14) 0.8552(3) 0.0178(6) Uani 1 1 d . . . H4A H 0.8765 0.8143 0.8245 0.021 Uiso 1 1 calc R . . H4B H 0.8509 0.8566 0.9396 0.021 Uiso 1 1 calc R . . C5 C 0.74039(14) 0.75134(14) 1.0487(3) 0.0171(5) Uani 1 1 d . . . C6 C 0.64055(14) 0.67543(13) 1.2289(3) 0.0171(6) Uani 1 1 d . . . C7 C 0.67875(14) 0.70655(14) 1.3636(3) 0.0192(6) Uani 1 1 d . . . H7 H 0.7303 0.7409 1.3618 0.080 Uiso 1 1 calc . . . C8 C 0.64057(15) 0.68673(14) 1.5002(3) 0.0211(6) Uani 1 1 d . . . H8 H 0.6662 0.7085 1.5922 0.080 Uiso 1 1 calc . . . C9 C 0.75113(14) 0.68652(13) 0.8160(3) 0.0166(5) Uani 1 1 d . . . C10 C 0.80085(14) 0.68311(15) 0.7107(3) 0.0216(6) Uani 1 1 d . . . H10 H 0.8511 0.7213 0.7066 0.080 Uiso 1 1 calc . . . C11 C 0.77487(14) 0.62414(15) 0.6161(3) 0.0221(6) Uani 1 1 d . . . H11 H 0.8065 0.6210 0.5423 0.080 Uiso 1 1 calc . . . C12 C 0.70033(14) 0.56727(14) 0.6282(3) 0.0177(6) Uani 1 1 d . . . C13 C 0.71999(14) 0.50069(14) 0.4162(3) 0.0188(6) Uani 1 1 d . . . H13A H 0.7013 0.4479 0.3926 0.023 Uiso 1 1 calc R . . H13B H 0.7700 0.5209 0.4608 0.023 Uiso 1 1 calc R . . C14 C 0.72616(14) 0.54159(14) 0.2685(3) 0.0207(6) Uani 1 1 d . . . H14A H 0.7431 0.5944 0.2934 0.025 Uiso 1 1 calc R . . C15 C 0.78451(16) 0.53896(17) 0.1684(3) 0.0297(7) Uani 1 1 d . . . H15A H 0.8314 0.5599 0.2242 0.045 Uiso 1 1 calc R . . H15B H 0.7915 0.5677 0.0754 0.045 Uiso 1 1 calc R . . H15C H 0.7682 0.4875 0.1412 0.045 Uiso 1 1 calc R . . C16 C 0.65239(16) 0.50915(16) 0.1847(3) 0.0288(7) Uani 1 1 d . . . H16A H 0.6158 0.5116 0.2506 0.043 Uiso 1 1 calc R . . H16B H 0.6353 0.4575 0.1583 0.043 Uiso 1 1 calc R . . H16C H 0.6587 0.5375 0.0914 0.043 Uiso 1 1 calc R . . C17 C 0.59767(14) 0.44455(14) 0.5325(3) 0.0198(6) Uani 1 1 d . . . C18 C 0.43401(15) 0.36395(14) 0.4946(3) 0.0210(6) Uani 1 1 d . . . H18 H 0.4591 0.3780 0.3996 0.080 Uiso 1 1 calc . . . C19 C 0.47230(14) 0.39437(13) 0.6296(3) 0.0175(5) Uani 1 1 d . . . C20 C 0.43594(14) 0.37417(13) 0.7703(3) 0.0173(6) Uani 1 1 d . . . C21 C 0.47678(15) 0.40509(15) 0.9179(3) 0.0227(6) Uani 1 1 d . . . H21A H 0.4421 0.3844 1.0034 0.034 Uiso 1 1 calc R . . H21B H 0.4993 0.4590 0.9175 0.034 Uiso 1 1 calc R . . H21C H 0.5155 0.3919 0.9289 0.034 Uiso 1 1 calc R . . C22 C 0.6667 0.3333 0.7401(6) 0.0351(13) Uani 1 3 d S . . H H 0.6667 0.3333 0.630(6) 0.039(15) Uiso 1 3 d S . . H6 H 0.6576(15) 0.6548(16) 1.017(3) 0.018(7) Uiso 1 1 d . . . H1 H 0.5672(16) 0.4869(17) 0.690(3) 0.029(8) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0499(6) 0.0369(5) 0.0487(5) -0.0007(4) -0.0106(4) 0.0151(4) O1 0.0266(11) 0.0165(10) 0.0381(12) -0.0076(9) 0.0103(9) 0.0043(9) O2 0.0214(10) 0.0160(10) 0.0249(10) -0.0036(8) 0.0018(8) 0.0064(8) N1 0.0170(12) 0.0156(12) 0.0221(12) -0.0040(10) 0.0021(9) 0.0041(10) N2 0.0168(11) 0.0159(11) 0.0213(11) -0.0027(9) 0.0015(9) 0.0068(10) N3 0.0184(12) 0.0165(11) 0.0183(11) -0.0017(9) 0.0006(9) 0.0074(10) N4 0.0168(11) 0.0174(12) 0.0186(11) -0.0005(9) 0.0002(9) 0.0066(10) N5 0.0163(11) 0.0125(11) 0.0200(11) -0.0021(9) 0.0000(9) 0.0054(9) N6 0.0181(12) 0.0174(12) 0.0190(12) -0.0032(10) 0.0014(9) 0.0060(10) C1 0.0283(16) 0.0258(16) 0.0355(17) 0.0046(13) 0.0054(13) 0.0114(14) C2 0.0213(14) 0.0199(14) 0.0225(14) 0.0003(11) 0.0016(11) 0.0097(12) C3 0.0263(16) 0.0243(15) 0.0350(16) 0.0002(12) -0.0021(12) 0.0140(13) C4 0.0117(12) 0.0160(13) 0.0221(13) -0.0006(10) 0.0010(10) 0.0041(11) C5 0.0152(13) 0.0163(13) 0.0208(13) 0.0012(11) 0.0001(10) 0.0087(11) C6 0.0180(13) 0.0132(13) 0.0207(13) 0.0007(10) 0.0014(11) 0.0082(11) C7 0.0199(14) 0.0167(13) 0.0219(13) -0.0033(11) -0.0020(11) 0.0099(12) C8 0.0233(15) 0.0196(14) 0.0217(14) -0.0007(11) -0.0028(11) 0.0116(12) C9 0.0168(13) 0.0151(13) 0.0180(13) 0.0005(10) -0.0014(10) 0.0080(11) C10 0.0158(13) 0.0211(14) 0.0258(14) -0.0017(11) 0.0016(11) 0.0077(12) C11 0.0177(14) 0.0240(15) 0.0249(14) -0.0018(11) 0.0030(11) 0.0108(12) C12 0.0181(13) 0.0171(13) 0.0195(13) 0.0008(10) -0.0003(11) 0.0099(11) C13 0.0171(13) 0.0176(13) 0.0224(14) -0.0031(11) 0.0019(11) 0.0093(11) C14 0.0212(14) 0.0152(13) 0.0235(14) -0.0009(11) 0.0025(11) 0.0075(12) C15 0.0298(16) 0.0299(16) 0.0249(15) -0.0002(12) 0.0053(12) 0.0115(14) C16 0.0302(16) 0.0268(16) 0.0289(15) 0.0051(12) -0.0013(13) 0.0139(13) C17 0.0198(14) 0.0151(13) 0.0229(14) 0.0015(11) 0.0023(11) 0.0074(12) C18 0.0251(15) 0.0176(14) 0.0194(13) 0.0016(11) 0.0019(11) 0.0101(12) C19 0.0174(13) 0.0124(13) 0.0220(13) -0.0004(10) 0.0018(10) 0.0071(11) C20 0.0184(13) 0.0138(13) 0.0190(13) -0.0025(10) -0.0008(10) 0.0074(11) C21 0.0207(14) 0.0215(14) 0.0200(14) -0.0035(11) -0.0009(11) 0.0061(12) C22 0.041(2) 0.041(2) 0.023(3) 0.000 0.000 0.0206(10) _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 Cl1 C22 1.753(2) . ? O1 C17 1.212(3) . ? O2 C5 1.226(3) . ? N1 C17 1.361(3) . ? N1 C19 1.417(3) . ? N1 H1 0.88(3) . ? N2 C12 1.400(3) . ? N2 C17 1.420(3) . ? N2 C13 1.482(3) . ? N3 C12 1.329(3) . ? N3 N4 1.354(3) . ? N4 C9 1.321(3) . ? N5 C9 1.409(3) . ? N5 C5 1.413(3) . ? N5 C4 1.476(3) . ? N6 C5 1.350(3) . ? N6 C6 1.412(3) . ? N6 H6 0.88(3) . ? C1 C2 1.523(4) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C4 1.522(4) . ? C2 C3 1.524(4) . ? C2 H2A 1.0000 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C6 C7 1.392(4) . ? C6 C20 1.404(4) 4_667 ? C7 C8 1.383(4) . ? C7 H7 0.9500 . ? C8 C18 1.379(4) 4_667 ? C8 H8 0.9500 . ? C9 C10 1.418(4) . ? C10 C11 1.353(4) . ? C10 H10 0.9500 . ? C11 C12 1.413(4) . ? C11 H11 0.9500 . ? C13 C14 1.522(4) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.526(4) . ? C14 C16 1.526(4) . ? C14 H14A 1.0000 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C18 C8 1.379(4) 4_667 ? C18 C19 1.392(4) . ? C18 H18 0.9500 . ? C19 C20 1.400(3) . ? C20 C6 1.404(4) 4_667 ? C20 C21 1.507(4) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 Cl1 1.7532(19) 3_665 ? C22 Cl1 1.7532(19) 2_655 ? C22 H 0.97(5) . ? 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 C17 N1 C19 122.6(2) . . ? C17 N1 H1 115.2(19) . . ? C19 N1 H1 122.0(19) . . ? C12 N2 C17 127.2(2) . . ? C12 N2 C13 118.5(2) . . ? C17 N2 C13 114.3(2) . . ? C12 N3 N4 120.8(2) . . ? C9 N4 N3 121.2(2) . . ? C9 N5 C5 126.6(2) . . ? C9 N5 C4 117.6(2) . . ? C5 N5 C4 115.5(2) . . ? C5 N6 C6 126.0(2) . . ? C5 N6 H6 116.1(18) . . ? C6 N6 H6 117.9(18) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C4 C2 C1 109.1(2) . . ? C4 C2 C3 111.8(2) . . ? C1 C2 C3 110.6(2) . . ? C4 C2 H2A 108.4 . . ? C1 C2 H2A 108.4 . . ? C3 C2 H2A 108.4 . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N5 C4 C2 113.3(2) . . ? N5 C4 H4A 108.9 . . ? C2 C4 H4A 108.9 . . ? N5 C4 H4B 108.9 . . ? C2 C4 H4B 108.9 . . ? H4A C4 H4B 107.7 . . ? O2 C5 N6 123.7(2) . . ? O2 C5 N5 120.0(2) . . ? N6 C5 N5 116.3(2) . . ? C7 C6 C20 121.1(2) . 4_667 ? C7 C6 N6 121.8(2) . . ? C20 C6 N6 117.1(2) 4_667 . ? C8 C7 C6 119.1(2) . . ? C8 C7 H7 120.5 . . ? C6 C7 H7 120.5 . . ? C18 C8 C7 121.3(2) 4_667 . ? C18 C8 H8 119.3 4_667 . ? C7 C8 H8 119.3 . . ? N4 C9 N5 119.0(2) . . ? N4 C9 C10 120.2(2) . . ? N5 C9 C10 120.8(2) . . ? C11 C10 C9 118.3(2) . . ? C11 C10 H10 120.8 . . ? C9 C10 H10 120.8 . . ? C10 C11 C12 119.4(2) . . ? C10 C11 H11 120.3 . . ? C12 C11 H11 120.3 . . ? N3 C12 N2 118.9(2) . . ? N3 C12 C11 119.8(2) . . ? N2 C12 C11 121.4(2) . . ? N2 C13 C14 113.9(2) . . ? N2 C13 H13A 108.8 . . ? C14 C13 H13A 108.8 . . ? N2 C13 H13B 108.8 . . ? C14 C13 H13B 108.8 . . ? H13A C13 H13B 107.7 . . ? C13 C14 C15 108.4(2) . . ? C13 C14 C16 112.2(2) . . ? C15 C14 C16 110.7(2) . . ? C13 C14 H14A 108.5 . . ? C15 C14 H14A 108.5 . . ? C16 C14 H14A 108.5 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O1 C17 N1 123.5(2) . . ? O1 C17 N2 119.5(2) . . ? N1 C17 N2 117.0(2) . . ? C8 C18 C19 119.5(2) 4_667 . ? C8 C18 H18 120.2 4_667 . ? C19 C18 H18 120.2 . . ? C18 C19 C20 120.8(2) . . ? C18 C19 N1 120.4(2) . . ? C20 C19 N1 118.8(2) . . ? C19 C20 C6 118.2(2) . 4_667 ? C19 C20 C21 121.6(2) . . ? C6 C20 C21 120.3(2) 4_667 . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? Cl1 C22 Cl1 110.61(16) . 3_665 ? Cl1 C22 Cl1 110.60(16) . 2_655 ? Cl1 C22 Cl1 110.60(16) 3_665 2_655 ? Cl1 C22 H 108.31(18) . . ? Cl1 C22 H 108.31(17) 3_665 . ? Cl1 C22 H 108.31(16) 2_655 . ? _diffrn_measured_fraction_theta_max 0.905 _diffrn_reflns_theta_full 26.97 _diffrn_measured_fraction_theta_full 0.905 _refine_diff_density_max 0.602 _refine_diff_density_min -0.528 _refine_diff_density_rms 0.063 data_z2 _database_code_depnum_ccdc_archive 'CCDC 267804' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H28 N6 O3' _chemical_formula_weight 412.49 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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.2501(12) _cell_length_b 15.874(3) _cell_length_c 19.137(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.558(2) _cell_angle_gamma 90.00 _cell_volume 2165.2(6) _cell_formula_units_Z 4 _cell_measurement_temperature 373(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.265 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 373(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16157 _diffrn_reflns_av_R_equivalents 0.0487 _diffrn_reflns_av_sigmaI/netI 0.0454 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3810 _reflns_number_gt 2329 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0897P)^2^+1.9938P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3810 _refine_ls_number_parameters 267 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1172 _refine_ls_R_factor_gt 0.0700 _refine_ls_wR_factor_ref 0.2213 _refine_ls_wR_factor_gt 0.1781 _refine_ls_goodness_of_fit_ref 1.100 _refine_ls_restrained_S_all 1.100 _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 O1 O -0.1957(4) 0.4145(2) -0.29685(14) 0.0664(8) Uani 1 1 d . . . O2 O 0.7752(3) 0.6417(2) 0.04774(14) 0.0626(8) Uani 1 1 d . . . O3 O 0.5195(10) 0.4479(8) -0.4031(5) 0.265(5) Uani 1 1 d . . . N1 N -0.0445(4) 0.3904(2) -0.18543(15) 0.0466(8) Uani 1 1 d . . . H1 H 0.0600 0.3930 -0.1559 0.056 Uiso 1 1 calc . . . N2 N 0.1003(4) 0.46503(19) -0.26670(14) 0.0441(7) Uani 1 1 d . . . N3 N 0.2164(4) 0.51829(19) -0.15407(15) 0.0481(8) Uani 1 1 d . . . N4 N 0.3541(4) 0.55056(19) -0.10470(15) 0.0461(8) Uani 1 1 d . . . N5 N 0.6610(4) 0.59771(18) -0.06463(15) 0.0422(7) Uani 1 1 d . . . N6 N 0.4615(4) 0.62514(19) 0.01728(15) 0.0448(8) Uani 1 1 d . . . H6A H 0.3730 0.6071 -0.0155 0.054 Uiso 1 1 calc R . . C1 C -0.0554(5) 0.4231(2) -0.25100(19) 0.0437(9) Uani 1 1 d . . . C2 C 0.0921(5) 0.4933(3) -0.34091(18) 0.0521(10) Uani 1 1 d . . . H2A H -0.0140 0.4664 -0.3709 0.063 Uiso 1 1 calc R . . H2B H 0.2049 0.4746 -0.3569 0.063 Uiso 1 1 calc R . . C3 C 0.0744(6) 0.5871(3) -0.3506(2) 0.0644(11) Uani 1 1 d . . . H3B H 0.1861 0.6129 -0.3220 0.077 Uiso 1 1 calc R . . C4 C -0.0944(8) 0.6226(4) -0.3255(3) 0.0995(18) Uani 1 1 d . . . H4B H -0.0897 0.6076 -0.2766 0.149 Uiso 1 1 calc R . . H4C H -0.2064 0.6000 -0.3538 0.149 Uiso 1 1 calc R . . H4D H -0.0947 0.6828 -0.3300 0.149 Uiso 1 1 calc R . . C5 C 0.0732(10) 0.6095(4) -0.4279(3) 0.120(2) Uani 1 1 d . . . H5A H 0.1816 0.5855 -0.4426 0.181 Uiso 1 1 calc R . . H5B H 0.0755 0.6696 -0.4330 0.181 Uiso 1 1 calc R . . H5C H -0.0383 0.5874 -0.4570 0.181 Uiso 1 1 calc R . . C6 C 0.2514(5) 0.4954(2) -0.21612(17) 0.0397(8) Uani 1 1 d . . . C7 C 0.4296(5) 0.5047(3) -0.23302(19) 0.0512(10) Uani 1 1 d . . . H7A H 0.4537 0.4874 -0.2769 0.061 Uiso 1 1 calc R . . C8 C 0.5651(5) 0.5392(3) -0.1843(2) 0.0516(10) Uani 1 1 d . . . H8A H 0.6849 0.5472 -0.1941 0.062 Uiso 1 1 calc R . . C9 C 0.5240(5) 0.5630(2) -0.11830(18) 0.0399(8) Uani 1 1 d . . . C10 C 0.8463(5) 0.6208(2) -0.0804(2) 0.0477(9) Uani 1 1 d . . . H10A H 0.8653 0.5901 -0.1224 0.057 Uiso 1 1 calc R A 1 H10B H 0.9423 0.6026 -0.0412 0.057 Uiso 1 1 calc R A 1 C14 C 0.6379(5) 0.6225(2) 0.00440(19) 0.0445(9) Uani 1 1 d . . . C15 C 0.4114(5) 0.6552(2) 0.08037(18) 0.0414(8) Uani 1 1 d . . . C16 C 0.5134(6) 0.7170(3) 0.1215(2) 0.0609(11) Uani 1 1 d . . . H16A H 0.6184 0.7406 0.1076 0.073 Uiso 1 1 calc R . . C17 C 0.4588(6) 0.7432(3) 0.1826(2) 0.0704(13) Uani 1 1 d . . . H17A H 0.5279 0.7848 0.2099 0.084 Uiso 1 1 calc R B . C18 C 0.3045(6) 0.7096(3) 0.2048(2) 0.0589(11) Uani 1 1 d . . . H18A H 0.2701 0.7280 0.2467 0.071 Uiso 1 1 calc R . . C19 C 0.2014(5) 0.6483(2) 0.16397(18) 0.0417(8) Uani 1 1 d . . . C20 C 0.2530(4) 0.6228(2) 0.10131(17) 0.0374(8) Uani 1 1 d . . . H20A H 0.1802 0.5833 0.0728 0.045 Uiso 1 1 calc R . . C11A C 0.7217(13) 0.7694(6) -0.1005(5) 0.079(3) Uiso 0.50 1 d P B 1 H11A H 0.6101 0.7385 -0.0970 0.119 Uiso 0.50 1 calc PR B 1 H11B H 0.7062 0.7965 -0.1461 0.119 Uiso 0.50 1 calc PR B 1 H11C H 0.7441 0.8112 -0.0637 0.119 Uiso 0.50 1 calc PR B 1 C12A C 0.8734(12) 0.7146(5) -0.0930(5) 0.056(2) Uiso 0.50 1 d P B 1 C13A C 1.0763(13) 0.7338(6) -0.0967(5) 0.067(2) Uiso 0.50 1 d P B 1 H13A H 1.0897 0.7929 -0.1052 0.100 Uiso 0.50 1 calc PR B 1 H13B H 1.1126 0.7021 -0.1347 0.100 Uiso 0.50 1 calc PR B 1 H13C H 1.1550 0.7185 -0.0525 0.100 Uiso 0.50 1 calc PR B 1 C21A C 0.522(4) 0.4420(19) -0.4729(14) 0.220(11) Uiso 0.50 1 d P C 1 H21A H 0.5128 0.4973 -0.4935 0.330 Uiso 0.50 1 calc PR C 1 H21B H 0.4170 0.4086 -0.4954 0.330 Uiso 0.50 1 calc PR C 1 H21C H 0.6364 0.4158 -0.4797 0.330 Uiso 0.50 1 calc PR C 1 C11B C 0.7505(16) 0.7424(8) -0.1577(6) 0.097(3) Uiso 0.50 1 d P B 2 H11D H 0.6210 0.7300 -0.1573 0.146 Uiso 0.50 1 calc PR B 2 H11E H 0.7711 0.7429 -0.2058 0.146 Uiso 0.50 1 calc PR B 2 H11F H 0.7814 0.7966 -0.1364 0.146 Uiso 0.50 1 calc PR B 2 C12B C 0.8336(12) 0.6972(5) -0.1293(5) 0.052(2) Uiso 0.50 1 d P B 2 C13B C 1.0228(14) 0.7265(7) -0.1362(6) 0.084(3) Uiso 0.50 1 d P B 2 H13D H 1.0121 0.7744 -0.1673 0.126 Uiso 0.50 1 calc PR B 2 H13E H 1.0880 0.6821 -0.1555 0.126 Uiso 0.50 1 calc PR B 2 H13F H 1.0914 0.7422 -0.0903 0.126 Uiso 0.50 1 calc PR B 2 C21B C 0.520(2) 0.3745(13) -0.4606(10) 0.154(6) Uiso 0.50 1 d P C 2 H21D H 0.5287 0.3208 -0.4372 0.232 Uiso 0.50 1 calc PR C 2 H21E H 0.6250 0.3819 -0.4840 0.232 Uiso 0.50 1 calc PR C 2 H21F H 0.4056 0.3770 -0.4951 0.232 Uiso 0.50 1 calc PR C 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 O1 0.0574(17) 0.092(2) 0.0451(16) 0.0032(14) -0.0019(14) -0.0111(15) O2 0.0420(15) 0.098(2) 0.0458(16) -0.0007(14) 0.0024(12) -0.0107(15) O3 0.155(6) 0.422(15) 0.202(8) -0.035(9) -0.009(5) 0.063(7) N1 0.0415(16) 0.062(2) 0.0366(17) -0.0011(14) 0.0081(13) -0.0061(14) N2 0.0495(17) 0.0490(18) 0.0355(16) -0.0041(13) 0.0121(13) -0.0001(14) N3 0.0458(17) 0.060(2) 0.0400(17) -0.0112(15) 0.0132(14) -0.0107(15) N4 0.0430(16) 0.0562(19) 0.0410(17) -0.0078(14) 0.0128(14) -0.0086(14) N5 0.0360(15) 0.0492(18) 0.0435(17) 0.0046(14) 0.0125(13) -0.0027(13) N6 0.0382(16) 0.058(2) 0.0384(17) -0.0058(14) 0.0071(13) -0.0096(14) C1 0.046(2) 0.047(2) 0.038(2) -0.0060(16) 0.0088(17) 0.0038(17) C2 0.061(2) 0.065(3) 0.033(2) -0.0027(18) 0.0126(17) 0.001(2) C3 0.074(3) 0.064(3) 0.055(3) 0.009(2) 0.012(2) 0.004(2) C4 0.102(4) 0.081(4) 0.118(5) 0.019(3) 0.027(3) 0.035(3) C5 0.163(6) 0.126(5) 0.073(4) 0.045(4) 0.023(4) 0.002(4) C6 0.0452(19) 0.0399(19) 0.0356(19) 0.0003(15) 0.0115(15) 0.0016(16) C7 0.052(2) 0.064(2) 0.041(2) -0.0071(18) 0.0179(18) 0.0022(19) C8 0.044(2) 0.063(3) 0.053(2) -0.0012(19) 0.0194(18) 0.0039(19) C9 0.0396(19) 0.0374(19) 0.044(2) 0.0052(15) 0.0116(16) 0.0008(15) C10 0.0375(19) 0.055(2) 0.053(2) 0.0097(18) 0.0132(16) -0.0010(17) C14 0.039(2) 0.054(2) 0.040(2) 0.0045(17) 0.0065(17) -0.0065(17) C15 0.0414(19) 0.045(2) 0.0378(19) -0.0025(16) 0.0069(15) -0.0066(16) C16 0.058(2) 0.066(3) 0.063(3) -0.017(2) 0.020(2) -0.028(2) C17 0.071(3) 0.076(3) 0.067(3) -0.034(2) 0.020(2) -0.034(2) C18 0.064(3) 0.063(3) 0.053(2) -0.024(2) 0.020(2) -0.014(2) C19 0.0397(19) 0.046(2) 0.040(2) -0.0047(16) 0.0090(16) -0.0026(16) C20 0.0373(18) 0.0368(19) 0.0368(19) -0.0041(14) 0.0031(14) -0.0056(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.223(4) . ? O2 C14 1.212(4) . ? O3 C21A 1.34(2) . ? O3 C21B 1.602(19) . ? N1 C1 1.347(4) . ? N1 C19 1.417(4) 3_565 ? N2 C1 1.390(4) . ? N2 C6 1.408(4) . ? N2 C2 1.480(4) . ? N3 C6 1.310(4) . ? N3 N4 1.344(4) . ? N4 C9 1.319(4) . ? N5 C9 1.404(4) . ? N5 C14 1.418(4) . ? N5 C10 1.476(4) . ? N6 C14 1.347(4) . ? N6 C15 1.406(4) . ? C2 C3 1.503(6) . ? C3 C4 1.503(6) . ? C3 C5 1.522(6) . ? C6 C7 1.396(5) . ? C7 C8 1.341(5) . ? C8 C9 1.402(5) . ? C10 C12B 1.525(9) . ? C10 C12A 1.526(9) . ? C15 C20 1.383(4) . ? C15 C16 1.384(5) . ? C16 C17 1.366(5) . ? C17 C18 1.375(5) . ? C18 C19 1.379(5) . ? C19 C20 1.381(5) . ? C19 N1 1.418(4) 3_565 ? C11A C12A 1.389(12) . ? C12A C13A 1.517(12) . ? C11B C12B 1.026(12) . ? C11B C13B 1.958(15) . ? C12B C13B 1.477(13) . ? 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 C21A O3 C21B 42.6(12) . . ? C1 N1 C19 121.6(3) . 3_565 ? C1 N2 C6 125.2(3) . . ? C1 N2 C2 117.5(3) . . ? C6 N2 C2 116.4(3) . . ? C6 N3 N4 120.0(3) . . ? C9 N4 N3 121.2(3) . . ? C9 N5 C14 127.0(3) . . ? C9 N5 C10 119.7(3) . . ? C14 N5 C10 112.9(3) . . ? C14 N6 C15 124.8(3) . . ? O1 C1 N1 121.6(3) . . ? O1 C1 N2 120.0(3) . . ? N1 C1 N2 118.4(3) . . ? N2 C2 C3 113.9(3) . . ? C2 C3 C4 112.9(4) . . ? C2 C3 C5 109.6(4) . . ? C4 C3 C5 111.3(4) . . ? N3 C6 C7 121.5(3) . . ? N3 C6 N2 117.5(3) . . ? C7 C6 N2 120.9(3) . . ? C8 C7 C6 118.2(3) . . ? C7 C8 C9 119.1(3) . . ? N4 C9 C8 119.9(3) . . ? N4 C9 N5 118.4(3) . . ? C8 C9 N5 121.7(3) . . ? N5 C10 C12B 111.6(4) . . ? N5 C10 C12A 115.0(4) . . ? C12B C10 C12A 28.6(4) . . ? O2 C14 N6 123.8(3) . . ? O2 C14 N5 119.0(3) . . ? N6 C14 N5 117.2(3) . . ? C20 C15 C16 119.0(3) . . ? C20 C15 N6 118.8(3) . . ? C16 C15 N6 122.3(3) . . ? C17 C16 C15 119.6(4) . . ? C16 C17 C18 121.7(4) . . ? C17 C18 C19 119.1(3) . . ? C18 C19 C20 119.6(3) . . ? C18 C19 N1 121.5(3) . 3_565 ? C20 C19 N1 118.9(3) . 3_565 ? C19 C20 C15 120.9(3) . . ? C11A C12A C13A 128.7(8) . . ? C11A C12A C10 120.4(7) . . ? C13A C12A C10 110.9(6) . . ? C12B C11B C13B 47.7(8) . . ? C11B C12B C13B 101.4(10) . . ? C11B C12B C10 147.6(10) . . ? C13B C12B C10 110.6(7) . . ? C12B C13B C11B 30.9(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 H1 N3 0.86 2.29 2.765(4) 115.3 . N6 H6A N4 0.86 1.91 2.606(4) 136.8 . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.491 _refine_diff_density_min -0.419 _refine_diff_density_rms 0.053