# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1-P-1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common jonjk13 _chemical_melting_point ? _chemical_formula_moiety 'C20 H24 N2 O4' _chemical_formula_sum 'C20 H24 N2 O4' _chemical_formula_weight 356.41 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 10.5300(12) _cell_length_b 12.5823(15) _cell_length_c 15.1214(18) _cell_angle_alpha 99.573(2) _cell_angle_beta 108.832(2) _cell_angle_gamma 97.267(2) _cell_volume 1834.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100.0(1) _cell_measurement_reflns_used 3974 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 32.85 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.290 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9579 _exptl_absorpt_correction_T_max 0.9875 _exptl_absorpt_process_details 'SADABS (Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100.0(1) _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 II CCD Platform' _diffrn_measurement_method 'area detector, \w scans per \f' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 31906 _diffrn_reflns_av_R_equivalents 0.0297 _diffrn_reflns_av_sigmaI/netI 0.0358 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _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 1.67 _diffrn_reflns_theta_max 31.51 _reflns_number_total 12131 _reflns_number_gt 9371 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2006)' _computing_cell_refinement 'SAINT (Bruker, 2006)' _computing_data_reduction 'SAINT (Bruker, 2006)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 2000)' _computing_publication_material 'SHELXTL (Bruker, 2000)' _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. All hydrogen atoms were found from the difference Fourier map. Their positions and isotropic displacement parameters were refined independently from all other atoms. ; _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^)+(0.0624P)^2^+0.3079P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 12131 _refine_ls_number_parameters 661 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0583 _refine_ls_R_factor_gt 0.0429 _refine_ls_wR_factor_ref 0.1208 _refine_ls_wR_factor_gt 0.1102 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 O1A O 0.75025(8) 0.28009(6) 0.79280(6) 0.02078(16) Uani 1 1 d . . . O2A O 0.71440(7) -0.00090(6) 0.52741(5) 0.01765(14) Uani 1 1 d . . . O3A O 0.03955(8) 0.29928(6) 0.63585(6) 0.02198(16) Uani 1 1 d . . . O4A O 0.13152(7) -0.05784(6) 0.66937(6) 0.02083(15) Uani 1 1 d . . . N1A N 0.44423(9) -0.04461(7) 0.73572(6) 0.01604(16) Uani 1 1 d . . . H1A H 0.3708(15) -0.0899(12) 0.6912(10) 0.022(3) Uiso 1 1 d . . . N2A N 0.48116(9) 0.23732(7) 0.84175(6) 0.01667(16) Uani 1 1 d . . . H2A H 0.5312(15) 0.2999(12) 0.8407(10) 0.025(3) Uiso 1 1 d . . . C1A C 0.41128(10) 0.04066(8) 0.80111(7) 0.01567(18) Uani 1 1 d . . . C2A C 0.54029(10) 0.13676(8) 0.83671(7) 0.01539(17) Uani 1 1 d . . . C3A C 0.59475(9) 0.11365(8) 0.75553(7) 0.01447(17) Uani 1 1 d . . . C4A C 0.53614(9) 0.00860(8) 0.69979(7) 0.01449(17) Uani 1 1 d . . . C5A C 0.34705(10) 0.21093(8) 0.77620(7) 0.01609(18) Uani 1 1 d . . . C6A C 0.30060(10) 0.09815(8) 0.75096(7) 0.01544(17) Uani 1 1 d . . . C7A C 0.37778(11) -0.00768(10) 0.87873(8) 0.0207(2) Uani 1 1 d . . . H7A H 0.2899(14) -0.0621(12) 0.8494(10) 0.023(3) Uiso 1 1 d . . . H7B H 0.4516(15) -0.0444(12) 0.9113(10) 0.025(4) Uiso 1 1 d . . . H7C H 0.3676(15) 0.0503(13) 0.9254(11) 0.029(4) Uiso 1 1 d . . . C8A C 0.64789(11) 0.13654(9) 0.93235(7) 0.0200(2) Uani 1 1 d . . . H8A H 0.7256(16) 0.1935(13) 0.9450(11) 0.033(4) Uiso 1 1 d . . . H8B H 0.6117(15) 0.1477(12) 0.9853(11) 0.028(4) Uiso 1 1 d . . . H8C H 0.6779(15) 0.0640(13) 0.9314(11) 0.030(4) Uiso 1 1 d . . . C9A C 0.69405(10) 0.17757(8) 0.73381(7) 0.01539(17) Uani 1 1 d . . . C10A C 0.73025(10) 0.13724(8) 0.65583(7) 0.01601(18) Uani 1 1 d . . . H10A H 0.7957(15) 0.1791(12) 0.6369(11) 0.029(4) Uiso 1 1 d . . . C11A C 0.66989(10) 0.03005(8) 0.60156(7) 0.01486(17) Uani 1 1 d . . . C12A C 0.57303(10) -0.03702(8) 0.62292(7) 0.01538(17) Uani 1 1 d . . . H12A H 0.5300(13) -0.1116(11) 0.5859(9) 0.016(3) Uiso 1 1 d . . . C13A C 0.86017(14) 0.34128(10) 0.77488(11) 0.0327(3) Uani 1 1 d . . . H13A H 0.8864(17) 0.4099(14) 0.8225(12) 0.041(4) Uiso 1 1 d . . . H13B H 0.9346(17) 0.3013(13) 0.7838(12) 0.038(4) Uiso 1 1 d . . . H13C H 0.8240(17) 0.3597(13) 0.7076(13) 0.040(4) Uiso 1 1 d . . . C14A C 0.66693(11) -0.11312(9) 0.47620(8) 0.01878(19) Uani 1 1 d . . . H14A H 0.7113(13) -0.1223(11) 0.4282(10) 0.018(3) Uiso 1 1 d . . . H14B H 0.6960(15) -0.1616(12) 0.5216(11) 0.026(4) Uiso 1 1 d . . . H14C H 0.5672(15) -0.1323(11) 0.4439(10) 0.023(3) Uiso 1 1 d . . . C15A C 0.26427(10) 0.28382(8) 0.74066(7) 0.01756(18) Uani 1 1 d . . . H15A H 0.2990(14) 0.3623(12) 0.7582(10) 0.023(3) Uiso 1 1 d . . . C16A C 0.13138(10) 0.23758(9) 0.67815(7) 0.01765(18) Uani 1 1 d . . . C17A C 0.08007(10) 0.12391(9) 0.65258(7) 0.01793(19) Uani 1 1 d . . . H17A H -0.0115(15) 0.0967(12) 0.6094(11) 0.027(4) Uiso 1 1 d . . . C18A C 0.16642(10) 0.05445(8) 0.69009(7) 0.01639(18) Uani 1 1 d . . . C19A C 0.08572(13) 0.41536(10) 0.66086(10) 0.0273(2) Uani 1 1 d . . . H19A H 0.0075(16) 0.4437(12) 0.6254(11) 0.029(4) Uiso 1 1 d . . . H19B H 0.1143(15) 0.4450(12) 0.7308(11) 0.027(4) Uiso 1 1 d . . . H19C H 0.1628(16) 0.4367(13) 0.6401(12) 0.034(4) Uiso 1 1 d . . . C20A C -0.00921(11) -0.10602(10) 0.61778(9) 0.0255(2) Uani 1 1 d . . . H20A H -0.0162(17) -0.1871(14) 0.6122(12) 0.038(4) Uiso 1 1 d . . . H20B H -0.0675(16) -0.0773(13) 0.6490(12) 0.035(4) Uiso 1 1 d . . . H20C H -0.0390(15) -0.0896(12) 0.5533(12) 0.030(4) Uiso 1 1 d . . . O1B O 0.06698(8) 0.40706(6) 0.08349(6) 0.02204(16) Uani 1 1 d . . . O2B O -0.03216(8) 0.04752(6) 0.13510(6) 0.02488(17) Uani 1 1 d . . . O3B O 0.60907(11) 0.65231(7) 0.51479(7) 0.0380(2) Uani 1 1 d . . . O4B O 0.67133(9) 0.30246(7) 0.35783(6) 0.02844(18) Uani 1 1 d . . . N1B N 0.42701(9) 0.22143(7) 0.16029(7) 0.01862(17) Uani 1 1 d . . . H1B H 0.4739(18) 0.1847(14) 0.1987(13) 0.041(4) Uiso 1 1 d . . . N2B N 0.38831(10) 0.50022(7) 0.17516(7) 0.02207(18) Uani 1 1 d . . . H2B H 0.3158(17) 0.5307(13) 0.1691(12) 0.034(4) Uiso 1 1 d . . . C1B C 0.48628(10) 0.33732(8) 0.17200(7) 0.01818(19) Uani 1 1 d . . . C2B C 0.35924(11) 0.38633(8) 0.11818(8) 0.01897(19) Uani 1 1 d . . . C3B C 0.24388(10) 0.30783(8) 0.12693(7) 0.01742(18) Uani 1 1 d . . . C4B C 0.28960(10) 0.21330(8) 0.14967(7) 0.01689(18) Uani 1 1 d . . . C5B C 0.46953(11) 0.50137(9) 0.26940(8) 0.0213(2) Uani 1 1 d . . . C6B C 0.52879(11) 0.40808(8) 0.27250(8) 0.0198(2) Uani 1 1 d . . . C7B C 0.60379(12) 0.34727(10) 0.13381(9) 0.0235(2) Uani 1 1 d . . . H7D H 0.6788(15) 0.3147(12) 0.1731(11) 0.029(4) Uiso 1 1 d . . . H7E H 0.5749(15) 0.3075(12) 0.0667(11) 0.026(4) Uiso 1 1 d . . . H7F H 0.6402(15) 0.4265(13) 0.1398(11) 0.030(4) Uiso 1 1 d . . . C8B C 0.33755(13) 0.38579(10) 0.01328(9) 0.0252(2) Uani 1 1 d . . . H8D H 0.2502(16) 0.4119(13) -0.0164(11) 0.034(4) Uiso 1 1 d . . . H8E H 0.4150(17) 0.4328(13) 0.0078(11) 0.036(4) Uiso 1 1 d . . . H8F H 0.3302(16) 0.3111(14) -0.0233(12) 0.036(4) Uiso 1 1 d . . . C9B C 0.10631(10) 0.31232(8) 0.10782(7) 0.01786(19) Uani 1 1 d . . . C10B C 0.01678(11) 0.22433(9) 0.11305(8) 0.01968(19) Uani 1 1 d . . . H10B H -0.0807(16) 0.2245(12) 0.1001(11) 0.030(4) Uiso 1 1 d . . . C11B C 0.06600(11) 0.12981(8) 0.13511(7) 0.01866(19) Uani 1 1 d . . . C12B C 0.20283(11) 0.12246(8) 0.15473(7) 0.01840(19) Uani 1 1 d . . . H12B H 0.2364(14) 0.0582(11) 0.1704(10) 0.022(3) Uiso 1 1 d . . . C13B C -0.07484(12) 0.41075(10) 0.05770(11) 0.0291(3) Uani 1 1 d . . . H13D H -0.0814(17) 0.4836(14) 0.0459(12) 0.038(4) Uiso 1 1 d . . . H13E H -0.1317(16) 0.3545(13) 0.0024(11) 0.031(4) Uiso 1 1 d . . . H13F H -0.1045(16) 0.4023(12) 0.1126(11) 0.031(4) Uiso 1 1 d . . . C14B C 0.00107(13) -0.05891(9) 0.13602(9) 0.0260(2) Uani 1 1 d . . . H14D H -0.0831(17) -0.1063(13) 0.1289(11) 0.034(4) Uiso 1 1 d . . . H14E H 0.0323(16) -0.0831(13) 0.0831(12) 0.038(4) Uiso 1 1 d . . . H14F H 0.0760(16) -0.0582(12) 0.1964(11) 0.031(4) Uiso 1 1 d . . . C15B C 0.49669(13) 0.58356(9) 0.35059(9) 0.0263(2) Uani 1 1 d . . . H15B H 0.4601(16) 0.6490(13) 0.3501(11) 0.032(4) Uiso 1 1 d . . . C16B C 0.58611(13) 0.56951(9) 0.43671(9) 0.0280(3) Uani 1 1 d . . . C17B C 0.64688(13) 0.47728(10) 0.44295(9) 0.0270(2) Uani 1 1 d . . . H17B H 0.7077(16) 0.4686(13) 0.5036(12) 0.034(4) Uiso 1 1 d . . . C18B C 0.61730(11) 0.39618(9) 0.35934(8) 0.0228(2) Uani 1 1 d . . . C19B C 0.70867(19) 0.64868(12) 0.60335(10) 0.0426(4) Uani 1 1 d . . . H19D H 0.7118(18) 0.7146(15) 0.6467(13) 0.043(5) Uiso 1 1 d . . . H19E H 0.6827(17) 0.5843(14) 0.6270(12) 0.041(4) Uiso 1 1 d . . . H19F H 0.8010(19) 0.6459(14) 0.5980(13) 0.046(5) Uiso 1 1 d . . . C20B C 0.75873(19) 0.28680(14) 0.44667(11) 0.0465(4) Uani 1 1 d . . . H20D H 0.7793(19) 0.2160(16) 0.4355(13) 0.050(5) Uiso 1 1 d . . . H20E H 0.8379(19) 0.3432(16) 0.4738(14) 0.049(5) Uiso 1 1 d . . . H20F H 0.7051(19) 0.2861(15) 0.4924(14) 0.050(5) 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 O1A 0.0175(3) 0.0150(3) 0.0268(4) -0.0048(3) 0.0108(3) -0.0030(3) O2A 0.0198(3) 0.0160(3) 0.0173(3) 0.0003(3) 0.0087(3) 0.0029(3) O3A 0.0177(3) 0.0208(4) 0.0271(4) 0.0063(3) 0.0060(3) 0.0059(3) O4A 0.0148(3) 0.0171(3) 0.0258(4) 0.0028(3) 0.0033(3) -0.0014(3) N1A 0.0143(4) 0.0152(4) 0.0168(4) 0.0022(3) 0.0047(3) 0.0001(3) N2A 0.0138(4) 0.0154(4) 0.0179(4) -0.0003(3) 0.0045(3) 0.0006(3) C1A 0.0140(4) 0.0168(4) 0.0152(4) 0.0027(3) 0.0050(3) 0.0010(3) C2A 0.0132(4) 0.0162(4) 0.0147(4) 0.0003(3) 0.0043(3) 0.0015(3) C3A 0.0126(4) 0.0152(4) 0.0142(4) 0.0017(3) 0.0039(3) 0.0020(3) C4A 0.0132(4) 0.0139(4) 0.0150(4) 0.0035(3) 0.0032(3) 0.0019(3) C5A 0.0142(4) 0.0190(4) 0.0149(4) 0.0014(3) 0.0065(3) 0.0021(3) C6A 0.0134(4) 0.0175(4) 0.0151(4) 0.0026(3) 0.0055(3) 0.0017(3) C7A 0.0188(5) 0.0263(5) 0.0186(5) 0.0079(4) 0.0080(4) 0.0025(4) C8A 0.0169(5) 0.0240(5) 0.0152(4) 0.0017(4) 0.0027(4) 0.0016(4) C9A 0.0132(4) 0.0122(4) 0.0182(4) -0.0002(3) 0.0046(3) 0.0008(3) C10A 0.0149(4) 0.0144(4) 0.0186(4) 0.0023(3) 0.0067(3) 0.0019(3) C11A 0.0149(4) 0.0155(4) 0.0144(4) 0.0026(3) 0.0051(3) 0.0047(3) C12A 0.0153(4) 0.0130(4) 0.0156(4) 0.0012(3) 0.0037(3) 0.0019(3) C13A 0.0267(6) 0.0203(5) 0.0485(8) -0.0098(5) 0.0231(6) -0.0083(4) C14A 0.0200(5) 0.0171(5) 0.0171(4) -0.0007(4) 0.0057(4) 0.0043(4) C15A 0.0167(4) 0.0167(4) 0.0197(5) 0.0018(4) 0.0082(4) 0.0024(3) C16A 0.0156(4) 0.0212(5) 0.0185(4) 0.0048(4) 0.0084(4) 0.0051(4) C17A 0.0128(4) 0.0219(5) 0.0180(4) 0.0033(4) 0.0050(3) 0.0018(3) C18A 0.0151(4) 0.0172(4) 0.0163(4) 0.0026(3) 0.0063(3) 0.0004(3) C19A 0.0229(5) 0.0211(5) 0.0371(7) 0.0095(5) 0.0076(5) 0.0052(4) C20A 0.0156(5) 0.0233(5) 0.0298(6) 0.0026(4) 0.0023(4) -0.0037(4) O1B 0.0171(3) 0.0154(3) 0.0320(4) 0.0050(3) 0.0058(3) 0.0055(3) O2B 0.0208(4) 0.0184(4) 0.0356(4) 0.0079(3) 0.0100(3) 0.0017(3) O3B 0.0565(6) 0.0227(4) 0.0298(5) -0.0083(3) 0.0227(4) -0.0114(4) O4B 0.0270(4) 0.0266(4) 0.0227(4) 0.0001(3) -0.0004(3) 0.0046(3) N1B 0.0162(4) 0.0162(4) 0.0222(4) 0.0031(3) 0.0051(3) 0.0046(3) N2B 0.0223(4) 0.0153(4) 0.0295(5) 0.0027(3) 0.0115(4) 0.0035(3) C1B 0.0167(4) 0.0169(4) 0.0202(5) 0.0014(4) 0.0071(4) 0.0028(3) C2B 0.0195(5) 0.0155(4) 0.0230(5) 0.0032(4) 0.0090(4) 0.0044(4) C3B 0.0175(4) 0.0157(4) 0.0182(4) 0.0019(3) 0.0059(4) 0.0036(3) C4B 0.0168(4) 0.0167(4) 0.0153(4) 0.0010(3) 0.0042(3) 0.0039(3) C5B 0.0213(5) 0.0165(5) 0.0275(5) 0.0016(4) 0.0138(4) -0.0010(4) C6B 0.0175(5) 0.0184(5) 0.0217(5) 0.0001(4) 0.0087(4) -0.0011(4) C7B 0.0203(5) 0.0253(5) 0.0271(6) 0.0034(4) 0.0120(4) 0.0051(4) C8B 0.0272(6) 0.0280(6) 0.0254(5) 0.0100(4) 0.0119(4) 0.0099(5) C9B 0.0185(5) 0.0144(4) 0.0188(5) 0.0016(3) 0.0046(4) 0.0045(3) C10B 0.0163(4) 0.0185(5) 0.0224(5) 0.0026(4) 0.0052(4) 0.0034(4) C11B 0.0186(5) 0.0169(4) 0.0184(5) 0.0021(4) 0.0055(4) 0.0008(3) C12B 0.0195(5) 0.0161(4) 0.0178(4) 0.0027(4) 0.0046(4) 0.0038(4) C13B 0.0180(5) 0.0213(5) 0.0433(7) 0.0067(5) 0.0038(5) 0.0061(4) C14B 0.0293(6) 0.0181(5) 0.0315(6) 0.0068(4) 0.0119(5) 0.0025(4) C15B 0.0318(6) 0.0158(5) 0.0324(6) -0.0017(4) 0.0192(5) -0.0032(4) C16B 0.0357(6) 0.0194(5) 0.0267(6) -0.0049(4) 0.0187(5) -0.0101(4) C17B 0.0303(6) 0.0241(5) 0.0213(5) -0.0014(4) 0.0102(4) -0.0079(4) C18B 0.0221(5) 0.0203(5) 0.0230(5) 0.0005(4) 0.0084(4) -0.0023(4) C19B 0.0624(10) 0.0302(7) 0.0266(6) -0.0065(5) 0.0215(6) -0.0198(6) C20B 0.0534(10) 0.0350(8) 0.0284(7) 0.0005(6) -0.0124(7) 0.0087(7) _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 O1A C9A 1.3759(12) . ? O1A C13A 1.4327(14) . ? O2A C11A 1.3671(12) . ? O2A C14A 1.4322(12) . ? O3A C16A 1.3793(12) . ? O3A C19A 1.4251(14) . ? O4A C18A 1.3699(12) . ? O4A C20A 1.4287(13) . ? N1A C4A 1.4058(12) . ? N1A C1A 1.4873(13) . ? N1A H1A 0.895(14) . ? N2A C5A 1.3984(13) . ? N2A C2A 1.4806(13) . ? N2A H2A 0.896(15) . ? C1A C6A 1.5104(14) . ? C1A C7A 1.5239(14) . ? C1A C2A 1.5790(14) . ? C2A C3A 1.5159(13) . ? C2A C8A 1.5231(14) . ? C3A C4A 1.3877(13) . ? C3A C9A 1.3946(13) . ? C4A C12A 1.3992(14) . ? C5A C6A 1.3865(14) . ? C5A C15A 1.3976(14) . ? C6A C18A 1.3933(13) . ? C7A H7A 0.998(14) . ? C7A H7B 0.990(15) . ? C7A H7C 0.969(16) . ? C8A H8A 0.961(16) . ? C8A H8B 0.990(15) . ? C8A H8C 1.002(15) . ? C9A C10A 1.3905(14) . ? C10A C11A 1.4052(14) . ? C10A H10A 0.959(15) . ? C11A C12A 1.3936(14) . ? C12A H12A 0.976(13) . ? C13A H13A 0.972(17) . ? C13A H13B 0.969(17) . ? C13A H13C 1.042(17) . ? C14A H14A 0.981(14) . ? C14A H14B 0.994(15) . ? C14A H14C 0.982(14) . ? C15A C16A 1.3955(14) . ? C15A H15A 0.969(14) . ? C16A C17A 1.4044(15) . ? C17A C18A 1.3948(14) . ? C17A H17A 0.953(15) . ? C19A H19A 0.973(15) . ? C19A H19B 0.992(15) . ? C19A H19C 0.983(16) . ? C20A H20A 1.001(17) . ? C20A H20B 0.958(17) . ? C20A H20C 0.989(16) . ? O1B C9B 1.3785(12) . ? O1B C13B 1.4255(14) . ? O2B C11B 1.3673(13) . ? O2B C14B 1.4274(14) . ? O3B C16B 1.3715(14) . ? O3B C19B 1.422(2) . ? O4B C18B 1.3726(14) . ? O4B C20B 1.4234(16) . ? N1B C4B 1.3918(13) . ? N1B C1B 1.4696(13) . ? N1B H1B 0.870(17) . ? N2B C5B 1.4020(15) . ? N2B C2B 1.4825(14) . ? N2B H2B 0.882(17) . ? C1B C6B 1.5207(15) . ? C1B C7B 1.5253(15) . ? C1B C2B 1.5828(15) . ? C2B C3B 1.5207(14) . ? C2B C8B 1.5266(16) . ? C3B C4B 1.3924(14) . ? C3B C9B 1.3932(14) . ? C4B C12B 1.3989(14) . ? C5B C15B 1.3910(15) . ? C5B C6B 1.3978(15) . ? C6B C18B 1.3878(16) . ? C7B H7D 1.003(15) . ? C7B H7E 0.983(15) . ? C7B H7F 1.001(15) . ? C8B H8D 1.007(16) . ? C8B H8E 0.979(17) . ? C8B H8F 0.988(17) . ? C9B C10B 1.3906(15) . ? C10B C11B 1.4037(15) . ? C10B H10B 0.981(15) . ? C11B C12B 1.3926(15) . ? C12B H12B 0.958(14) . ? C13B H13D 0.968(17) . ? C13B H13E 0.965(16) . ? C13B H13F 0.992(16) . ? C14B H14D 0.967(16) . ? C14B H14E 0.977(17) . ? C14B H14F 0.993(16) . ? C15B C16B 1.3931(19) . ? C15B H15B 0.953(16) . ? C16B C17B 1.3966(19) . ? C17B C18B 1.4047(16) . ? C17B H17B 0.967(16) . ? C19B H19D 0.958(18) . ? C19B H19E 0.981(17) . ? C19B H19F 1.005(19) . ? C20B H20D 0.944(19) . ? C20B H20E 0.948(19) . ? C20B H20F 1.02(2) . ? 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 C9A O1A C13A 115.62(8) . . ? C11A O2A C14A 116.25(8) . . ? C16A O3A C19A 116.53(9) . . ? C18A O4A C20A 117.22(9) . . ? C4A N1A C1A 107.82(8) . . ? C4A N1A H1A 115.0(9) . . ? C1A N1A H1A 114.1(9) . . ? C5A N2A C2A 107.77(8) . . ? C5A N2A H2A 115.4(9) . . ? C2A N2A H2A 117.9(9) . . ? N1A C1A C6A 114.28(8) . . ? N1A C1A C7A 110.30(8) . . ? C6A C1A C7A 111.38(8) . . ? N1A C1A C2A 103.76(7) . . ? C6A C1A C2A 100.63(8) . . ? C7A C1A C2A 116.12(8) . . ? N2A C2A C3A 114.53(8) . . ? N2A C2A C8A 111.37(8) . . ? C3A C2A C8A 111.13(8) . . ? N2A C2A C1A 103.59(7) . . ? C3A C2A C1A 100.61(7) . . ? C8A C2A C1A 115.09(8) . . ? C4A C3A C9A 118.87(9) . . ? C4A C3A C2A 110.57(8) . . ? C9A C3A C2A 130.48(9) . . ? C3A C4A C12A 122.98(9) . . ? C3A C4A N1A 110.42(8) . . ? C12A C4A N1A 126.48(9) . . ? C6A C5A C15A 122.13(9) . . ? C6A C5A N2A 110.55(9) . . ? C15A C5A N2A 127.28(9) . . ? C5A C6A C18A 119.91(9) . . ? C5A C6A C1A 110.34(8) . . ? C18A C6A C1A 129.71(9) . . ? C1A C7A H7A 109.6(8) . . ? C1A C7A H7B 110.4(8) . . ? H7A C7A H7B 109.4(11) . . ? C1A C7A H7C 109.7(9) . . ? H7A C7A H7C 108.6(12) . . ? H7B C7A H7C 109.3(12) . . ? C2A C8A H8A 108.9(9) . . ? C2A C8A H8B 111.7(9) . . ? H8A C8A H8B 110.0(13) . . ? C2A C8A H8C 111.0(9) . . ? H8A C8A H8C 109.2(13) . . ? H8B C8A H8C 105.9(12) . . ? O1A C9A C10A 123.69(9) . . ? O1A C9A C3A 116.13(9) . . ? C10A C9A C3A 120.17(9) . . ? C9A C10A C11A 119.40(9) . . ? C9A C10A H10A 123.1(9) . . ? C11A C10A H10A 117.5(9) . . ? O2A C11A C12A 124.03(9) . . ? O2A C11A C10A 114.14(8) . . ? C12A C11A C10A 121.83(9) . . ? C11A C12A C4A 116.68(9) . . ? C11A C12A H12A 122.9(8) . . ? C4A C12A H12A 120.4(8) . . ? O1A C13A H13A 104.0(10) . . ? O1A C13A H13B 109.3(10) . . ? H13A C13A H13B 111.3(14) . . ? O1A C13A H13C 109.8(9) . . ? H13A C13A H13C 107.6(13) . . ? H13B C13A H13C 114.3(14) . . ? O2A C14A H14A 105.8(8) . . ? O2A C14A H14B 108.9(8) . . ? H14A C14A H14B 110.2(11) . . ? O2A C14A H14C 113.2(8) . . ? H14A C14A H14C 109.4(11) . . ? H14B C14A H14C 109.3(12) . . ? C16A C15A C5A 116.68(9) . . ? C16A C15A H15A 122.3(8) . . ? C5A C15A H15A 121.0(8) . . ? O3A C16A C15A 123.01(9) . . ? O3A C16A C17A 114.29(9) . . ? C15A C16A C17A 122.71(9) . . ? C18A C17A C16A 118.52(9) . . ? C18A C17A H17A 122.3(9) . . ? C16A C17A H17A 119.2(9) . . ? O4A C18A C6A 115.09(9) . . ? O4A C18A C17A 124.85(9) . . ? C6A C18A C17A 120.02(9) . . ? O3A C19A H19A 104.2(9) . . ? O3A C19A H19B 112.0(8) . . ? H19A C19A H19B 111.5(12) . . ? O3A C19A H19C 111.4(9) . . ? H19A C19A H19C 109.2(13) . . ? H19B C19A H19C 108.6(13) . . ? O4A C20A H20A 106.1(9) . . ? O4A C20A H20B 111.8(10) . . ? H20A C20A H20B 112.0(14) . . ? O4A C20A H20C 110.7(9) . . ? H20A C20A H20C 110.0(13) . . ? H20B C20A H20C 106.3(13) . . ? C9B O1B C13B 117.11(9) . . ? C11B O2B C14B 117.55(9) . . ? C16B O3B C19B 118.26(12) . . ? C18B O4B C20B 117.42(10) . . ? C4B N1B C1B 108.49(8) . . ? C4B N1B H1B 116.7(11) . . ? C1B N1B H1B 117.5(11) . . ? C5B N2B C2B 107.77(9) . . ? C5B N2B H2B 115.4(11) . . ? C2B N2B H2B 114.8(11) . . ? N1B C1B C6B 115.65(9) . . ? N1B C1B C7B 110.81(9) . . ? C6B C1B C7B 110.93(9) . . ? N1B C1B C2B 103.37(8) . . ? C6B C1B C2B 100.35(8) . . ? C7B C1B C2B 115.30(9) . . ? N2B C2B C3B 115.77(8) . . ? N2B C2B C8B 110.85(9) . . ? C3B C2B C8B 110.90(9) . . ? N2B C2B C1B 103.55(8) . . ? C3B C2B C1B 100.21(8) . . ? C8B C2B C1B 115.12(9) . . ? C4B C3B C9B 118.98(9) . . ? C4B C3B C2B 109.59(9) . . ? C9B C3B C2B 131.12(9) . . ? N1B C4B C3B 110.60(9) . . ? N1B C4B C12B 126.75(9) . . ? C3B C4B C12B 122.55(9) . . ? C15B C5B C6B 122.23(11) . . ? C15B C5B N2B 127.16(11) . . ? C6B C5B N2B 110.54(9) . . ? C18B C6B C5B 119.25(10) . . ? C18B C6B C1B 130.82(10) . . ? C5B C6B C1B 109.84(9) . . ? C1B C7B H7D 108.8(9) . . ? C1B C7B H7E 111.6(8) . . ? H7D C7B H7E 108.1(12) . . ? C1B C7B H7F 109.7(9) . . ? H7D C7B H7F 108.7(12) . . ? H7E C7B H7F 109.9(12) . . ? C2B C8B H8D 109.4(9) . . ? C2B C8B H8E 110.6(9) . . ? H8D C8B H8E 110.3(13) . . ? C2B C8B H8F 111.2(9) . . ? H8D C8B H8F 108.2(13) . . ? H8E C8B H8F 107.1(13) . . ? O1B C9B C10B 123.54(9) . . ? O1B C9B C3B 116.10(9) . . ? C10B C9B C3B 120.36(9) . . ? C9B C10B C11B 119.14(10) . . ? C9B C10B H10B 122.7(9) . . ? C11B C10B H10B 118.1(9) . . ? O2B C11B C12B 124.07(9) . . ? O2B C11B C10B 113.87(9) . . ? C12B C11B C10B 122.06(10) . . ? C11B C12B C4B 116.88(9) . . ? C11B C12B H12B 121.9(8) . . ? C4B C12B H12B 121.2(8) . . ? O1B C13B H13D 104.9(10) . . ? O1B C13B H13E 113.1(9) . . ? H13D C13B H13E 111.4(13) . . ? O1B C13B H13F 109.3(9) . . ? H13D C13B H13F 109.3(13) . . ? H13E C13B H13F 108.8(13) . . ? O2B C14B H14D 105.0(9) . . ? O2B C14B H14E 110.7(9) . . ? H14D C14B H14E 110.8(13) . . ? O2B C14B H14F 110.9(9) . . ? H14D C14B H14F 112.1(13) . . ? H14E C14B H14F 107.4(13) . . ? C5B C15B C16B 117.25(11) . . ? C5B C15B H15B 123.9(10) . . ? C16B C15B H15B 118.8(9) . . ? O3B C16B C15B 115.11(12) . . ? O3B C16B C17B 122.58(12) . . ? C15B C16B C17B 122.30(11) . . ? C16B C17B C18B 118.79(11) . . ? C16B C17B H17B 121.0(10) . . ? C18B C17B H17B 120.2(10) . . ? O4B C18B C6B 116.48(10) . . ? O4B C18B C17B 123.35(11) . . ? C6B C18B C17B 120.17(11) . . ? O3B C19B H19D 104.9(11) . . ? O3B C19B H19E 111.7(10) . . ? H19D C19B H19E 110.0(14) . . ? O3B C19B H19F 112.1(10) . . ? H19D C19B H19F 110.8(15) . . ? H19E C19B H19F 107.5(14) . . ? O4B C20B H20D 107.6(11) . . ? O4B C20B H20E 111.2(11) . . ? H20D C20B H20E 112.9(16) . . ? O4B C20B H20F 108.5(11) . . ? H20D C20B H20F 106.3(15) . . ? H20E C20B H20F 110.1(15) . . ? 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 C4A N1A C1A C6A 82.89(10) . . . . ? C4A N1A C1A C7A -150.72(8) . . . . ? C4A N1A C1A C2A -25.70(10) . . . . ? C5A N2A C2A C3A 82.10(10) . . . . ? C5A N2A C2A C8A -150.73(8) . . . . ? C5A N2A C2A C1A -26.46(10) . . . . ? N1A C1A C2A N2A 142.59(8) . . . . ? C6A C1A C2A N2A 24.12(9) . . . . ? C7A C1A C2A N2A -96.22(10) . . . . ? N1A C1A C2A C3A 23.92(9) . . . . ? C6A C1A C2A C3A -94.56(8) . . . . ? C7A C1A C2A C3A 145.10(9) . . . . ? N1A C1A C2A C8A -95.60(9) . . . . ? C6A C1A C2A C8A 145.93(8) . . . . ? C7A C1A C2A C8A 25.59(12) . . . . ? N2A C2A C3A C4A -125.58(9) . . . . ? C8A C2A C3A C4A 107.14(9) . . . . ? C1A C2A C3A C4A -15.20(10) . . . . ? N2A C2A C3A C9A 57.80(13) . . . . ? C8A C2A C3A C9A -69.49(13) . . . . ? C1A C2A C3A C9A 168.17(10) . . . . ? C9A C3A C4A C12A 0.65(14) . . . . ? C2A C3A C4A C12A -176.42(9) . . . . ? C9A C3A C4A N1A 176.93(8) . . . . ? C2A C3A C4A N1A -0.14(11) . . . . ? C1A N1A C4A C3A 16.94(10) . . . . ? C1A N1A C4A C12A -166.95(9) . . . . ? C2A N2A C5A C6A 18.11(11) . . . . ? C2A N2A C5A C15A -163.88(9) . . . . ? C15A C5A C6A C18A -1.55(15) . . . . ? N2A C5A C6A C18A 176.58(9) . . . . ? C15A C5A C6A C1A -179.27(9) . . . . ? N2A C5A C6A C1A -1.14(11) . . . . ? N1A C1A C6A C5A -125.22(9) . . . . ? C7A C1A C6A C5A 108.96(10) . . . . ? C2A C1A C6A C5A -14.72(10) . . . . ? N1A C1A C6A C18A 57.35(13) . . . . ? C7A C1A C6A C18A -68.47(13) . . . . ? C2A C1A C6A C18A 167.85(10) . . . . ? C13A O1A C9A C10A -5.70(15) . . . . ? C13A O1A C9A C3A 174.89(10) . . . . ? C4A C3A C9A O1A -178.75(9) . . . . ? C2A C3A C9A O1A -2.36(15) . . . . ? C4A C3A C9A C10A 1.82(14) . . . . ? C2A C3A C9A C10A 178.21(9) . . . . ? O1A C9A C10A C11A 178.09(9) . . . . ? C3A C9A C10A C11A -2.52(15) . . . . ? C14A O2A C11A C12A -6.52(13) . . . . ? C14A O2A C11A C10A 173.65(8) . . . . ? C9A C10A C11A O2A -179.36(9) . . . . ? C9A C10A C11A C12A 0.80(15) . . . . ? O2A C11A C12A C4A -178.28(9) . . . . ? C10A C11A C12A C4A 1.53(14) . . . . ? C3A C4A C12A C11A -2.28(14) . . . . ? N1A C4A C12A C11A -177.94(9) . . . . ? C6A C5A C15A C16A 0.10(14) . . . . ? N2A C5A C15A C16A -177.70(9) . . . . ? C19A O3A C16A C15A -1.48(14) . . . . ? C19A O3A C16A C17A 178.85(10) . . . . ? C5A C15A C16A O3A -178.42(9) . . . . ? C5A C15A C16A C17A 1.22(15) . . . . ? O3A C16A C17A C18A 178.60(9) . . . . ? C15A C16A C17A C18A -1.07(15) . . . . ? C20A O4A C18A C6A 171.95(9) . . . . ? C20A O4A C18A C17A -10.25(15) . . . . ? C5A C6A C18A O4A 179.61(9) . . . . ? C1A C6A C18A O4A -3.17(15) . . . . ? C5A C6A C18A C17A 1.70(15) . . . . ? C1A C6A C18A C17A 178.92(9) . . . . ? C16A C17A C18A O4A -178.12(9) . . . . ? C16A C17A C18A C6A -0.42(15) . . . . ? C4B N1B C1B C6B 81.76(11) . . . . ? C4B N1B C1B C7B -150.91(9) . . . . ? C4B N1B C1B C2B -26.84(10) . . . . ? C5B N2B C2B C3B 81.08(11) . . . . ? C5B N2B C2B C8B -151.50(9) . . . . ? C5B N2B C2B C1B -27.51(10) . . . . ? N1B C1B C2B N2B 145.76(8) . . . . ? C6B C1B C2B N2B 26.04(10) . . . . ? C7B C1B C2B N2B -93.16(10) . . . . ? N1B C1B C2B C3B 25.90(9) . . . . ? C6B C1B C2B C3B -93.81(9) . . . . ? C7B C1B C2B C3B 146.99(9) . . . . ? N1B C1B C2B C8B -93.09(10) . . . . ? C6B C1B C2B C8B 147.20(9) . . . . ? C7B C1B C2B C8B 27.99(13) . . . . ? N2B C2B C3B C4B -128.10(10) . . . . ? C8B C2B C3B C4B 104.50(10) . . . . ? C1B C2B C3B C4B -17.54(10) . . . . ? N2B C2B C3B C9B 58.54(15) . . . . ? C8B C2B C3B C9B -68.86(14) . . . . ? C1B C2B C3B C9B 169.10(11) . . . . ? C1B N1B C4B C3B 16.52(11) . . . . ? C1B N1B C4B C12B -167.05(10) . . . . ? C9B C3B C4B N1B 176.19(9) . . . . ? C2B C3B C4B N1B 1.90(12) . . . . ? C9B C3B C4B C12B -0.42(15) . . . . ? C2B C3B C4B C12B -174.71(9) . . . . ? C2B N2B C5B C15B -165.30(10) . . . . ? C2B N2B C5B C6B 17.62(11) . . . . ? C15B C5B C6B C18B 0.33(16) . . . . ? N2B C5B C6B C18B 177.58(9) . . . . ? C15B C5B C6B C1B -176.56(10) . . . . ? N2B C5B C6B C1B 0.69(12) . . . . ? N1B C1B C6B C18B 56.25(15) . . . . ? C7B C1B C6B C18B -71.03(14) . . . . ? C2B C1B C6B C18B 166.64(11) . . . . ? N1B C1B C6B C5B -127.33(9) . . . . ? C7B C1B C6B C5B 105.39(10) . . . . ? C2B C1B C6B C5B -16.94(10) . . . . ? C13B O1B C9B C10B -3.42(15) . . . . ? C13B O1B C9B C3B 176.13(10) . . . . ? C4B C3B C9B O1B -178.46(9) . . . . ? C2B C3B C9B O1B -5.60(16) . . . . ? C4B C3B C9B C10B 1.10(15) . . . . ? C2B C3B C9B C10B 173.96(10) . . . . ? O1B C9B C10B C11B 177.70(9) . . . . ? C3B C9B C10B C11B -1.83(16) . . . . ? C14B O2B C11B C12B -13.14(15) . . . . ? C14B O2B C11B C10B 166.71(10) . . . . ? C9B C10B C11B O2B -177.93(9) . . . . ? C9B C10B C11B C12B 1.92(16) . . . . ? O2B C11B C12B C4B 178.62(9) . . . . ? C10B C11B C12B C4B -1.22(15) . . . . ? N1B C4B C12B C11B -175.57(10) . . . . ? C3B C4B C12B C11B 0.47(15) . . . . ? C6B C5B C15B C16B -0.21(16) . . . . ? N2B C5B C15B C16B -176.98(10) . . . . ? C19B O3B C16B C15B -174.31(10) . . . . ? C19B O3B C16B C17B 6.20(17) . . . . ? C5B C15B C16B O3B -179.63(10) . . . . ? C5B C15B C16B C17B -0.14(17) . . . . ? O3B C16B C17B C18B 179.80(10) . . . . ? C15B C16B C17B C18B 0.35(17) . . . . ? C20B O4B C18B C6B -177.93(13) . . . . ? C20B O4B C18B C17B 1.69(18) . . . . ? C5B C6B C18B O4B 179.52(9) . . . . ? C1B C6B C18B O4B -4.34(17) . . . . ? C5B C6B C18B C17B -0.11(16) . . . . ? C1B C6B C18B C17B 176.03(10) . . . . ? C16B C17B C18B O4B -179.82(10) . . . . ? C16B C17B C18B C6B -0.22(16) . . . . ? 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 N2A H2A N2B 0.896(15) 2.626(15) 3.4956(13) 164.1(12) 2_666 N2A H2A O1A 0.896(15) 2.659(15) 3.1569(12) 116.1(11) . N1A H1A O4A 0.895(14) 2.527(14) 3.0904(12) 121.5(11) . N1A H1A O4B 0.895(14) 2.593(14) 3.2205(13) 127.8(11) 2_656 N1B H1B N1A 0.870(17) 2.291(17) 3.1324(13) 162.8(16) 2_656 N2B H2B O1A 0.882(17) 2.590(16) 3.3220(13) 141.0(13) 2_666 N2B H2B O1B 0.882(17) 2.659(16) 3.1895(13) 119.7(13) . _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 31.51 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.380 _refine_diff_density_min -0.372 _refine_diff_density_rms 0.049 _database_code_depnum_ccdc_archive 'CCDC 774003' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common jonjk48 _chemical_melting_point ? _chemical_formula_moiety 'C22 H19 N O3' _chemical_formula_sum 'C22 H19 N O3' _chemical_formula_weight 345.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' 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 8.4671(19) _cell_length_b 23.820(5) _cell_length_c 8.7557(18) _cell_angle_alpha 90.00 _cell_angle_beta 99.090(5) _cell_angle_gamma 90.00 _cell_volume 1743.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100.0(1) _cell_measurement_reflns_used 3489 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 32.85 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.316 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9691 _exptl_absorpt_correction_T_max 0.9965 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100.0(1) _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 II CCD Platform' _diffrn_measurement_method 'area detector, \w scans per \f' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17805 _diffrn_reflns_av_R_equivalents 0.0851 _diffrn_reflns_av_sigmaI/netI 0.0802 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 33 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.44 _diffrn_reflns_theta_max 29.57 _reflns_number_total 4890 _reflns_number_gt 2930 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2009)' _computing_cell_refinement 'SAINT (Bruker, 2008)' _computing_data_reduction 'SAINT (Bruker, 2008)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0419P)^2^+0.0831P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4890 _refine_ls_number_parameters 311 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1076 _refine_ls_R_factor_gt 0.0516 _refine_ls_wR_factor_ref 0.1126 _refine_ls_wR_factor_gt 0.0938 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.05183(15) 0.34825(5) 0.14554(13) 0.0241(3) Uani 1 1 d . . . O2 O 0.53358(15) 0.59044(5) 0.29028(13) 0.0244(3) Uani 1 1 d . . . O3 O 0.20037(15) 0.50114(5) -0.14363(12) 0.0213(3) Uani 1 1 d . . . N1 N 0.15782(16) 0.45370(6) 0.38060(15) 0.0165(3) Uani 1 1 d . . . C1 C 0.12736(19) 0.40104(7) 0.37379(18) 0.0162(3) Uani 1 1 d . . . C2 C 0.1627(2) 0.36209(7) 0.24567(18) 0.0170(3) Uani 1 1 d . . . C3 C 0.05626(19) 0.37405(7) 0.49929(17) 0.0156(3) Uani 1 1 d . . . C4 C 0.0423(2) 0.31585(7) 0.50743(19) 0.0185(4) Uani 1 1 d . . . H4 H 0.076(2) 0.2926(7) 0.4276(19) 0.017(5) Uiso 1 1 d . . . C5 C -0.0143(2) 0.29051(8) 0.6307(2) 0.0216(4) Uani 1 1 d . . . H5 H -0.025(2) 0.2492(8) 0.6366(19) 0.023(5) Uiso 1 1 d . . . C6 C -0.0573(2) 0.32361(8) 0.7479(2) 0.0217(4) Uani 1 1 d . . . H6 H -0.094(2) 0.3059(8) 0.834(2) 0.027(5) Uiso 1 1 d . . . C7 C -0.0459(2) 0.38149(8) 0.74022(19) 0.0197(4) Uani 1 1 d . . . H7 H -0.076(2) 0.4054(7) 0.819(2) 0.020(5) Uiso 1 1 d . . . C8 C 0.0102(2) 0.40673(8) 0.61720(18) 0.0177(4) Uani 1 1 d . . . H8 H 0.019(2) 0.4482(9) 0.611(2) 0.034(6) Uiso 1 1 d . . . C9 C 0.3275(2) 0.34073(7) 0.25213(18) 0.0190(4) Uani 1 1 d . . . C10 C 0.3612(2) 0.30153(8) 0.1436(2) 0.0267(4) Uani 1 1 d . . . H10 H 0.270(2) 0.2901(8) 0.062(2) 0.023(5) Uiso 1 1 d . . . C11 C 0.5145(3) 0.28047(9) 0.1518(2) 0.0343(5) Uani 1 1 d . . . H11 H 0.539(3) 0.2545(9) 0.082(2) 0.047(7) Uiso 1 1 d . . . C12 C 0.6354(3) 0.29858(9) 0.2676(2) 0.0324(5) Uani 1 1 d . . . H12 H 0.739(3) 0.2841(9) 0.274(2) 0.042(6) Uiso 1 1 d . . . C13 C 0.6032(2) 0.33708(8) 0.3759(2) 0.0265(4) Uani 1 1 d . . . H13 H 0.687(2) 0.3499(8) 0.460(2) 0.032(6) Uiso 1 1 d . . . C14 C 0.4492(2) 0.35812(8) 0.3689(2) 0.0206(4) Uani 1 1 d . . . H14 H 0.422(2) 0.3834(7) 0.444(2) 0.020(5) Uiso 1 1 d . . . C15 C 0.2319(2) 0.48227(7) 0.26843(18) 0.0159(3) Uani 1 1 d . . . C16 C 0.3488(2) 0.52125(7) 0.32529(18) 0.0171(4) Uani 1 1 d . . . H16 H 0.3772(19) 0.5249(7) 0.4370(18) 0.010(4) Uiso 1 1 d . . . C17 C 0.4185(2) 0.55366(7) 0.22349(18) 0.0180(4) Uani 1 1 d . . . C18 C 0.3721(2) 0.54896(7) 0.06442(18) 0.0177(4) Uani 1 1 d . . . H18 H 0.420(2) 0.5715(7) -0.0061(18) 0.013(4) Uiso 1 1 d . . . C19 C 0.2544(2) 0.50977(7) 0.00987(18) 0.0170(4) Uani 1 1 d . . . C20 C 0.1834(2) 0.47648(7) 0.10975(19) 0.0177(3) Uani 1 1 d . . . H20 H 0.096(2) 0.4520(7) 0.0691(19) 0.019(5) Uiso 1 1 d . . . C21 C 0.5978(2) 0.62880(9) 0.1907(2) 0.0255(4) Uani 1 1 d . . . H21A H 0.672(2) 0.6542(8) 0.258(2) 0.027(5) Uiso 1 1 d . . . H21B H 0.660(3) 0.6085(9) 0.116(2) 0.038(6) Uiso 1 1 d . . . H21C H 0.509(3) 0.6525(8) 0.133(2) 0.031(5) Uiso 1 1 d . . . C22 C 0.2523(2) 0.53966(8) -0.2504(2) 0.0214(4) Uani 1 1 d . . . H22A H 0.202(2) 0.5281(8) -0.350(2) 0.025(5) Uiso 1 1 d . . . H22B H 0.219(2) 0.5792(9) -0.227(2) 0.026(5) Uiso 1 1 d . . . H22C H 0.368(2) 0.5369(7) -0.2436(18) 0.019(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0298(7) 0.0218(7) 0.0197(6) -0.0008(5) 0.0004(5) -0.0045(6) O2 0.0273(7) 0.0261(7) 0.0191(6) 0.0012(5) 0.0019(5) -0.0106(6) O3 0.0281(7) 0.0225(7) 0.0133(5) 0.0006(5) 0.0034(5) -0.0062(5) N1 0.0171(7) 0.0168(7) 0.0164(6) 0.0012(6) 0.0052(5) 0.0014(6) C1 0.0146(8) 0.0184(9) 0.0152(7) 0.0006(6) 0.0016(6) 0.0017(7) C2 0.0234(9) 0.0127(8) 0.0158(7) 0.0021(6) 0.0058(7) -0.0017(7) C3 0.0147(8) 0.0159(8) 0.0160(7) 0.0008(6) 0.0021(6) 0.0004(7) C4 0.0202(9) 0.0182(9) 0.0177(8) -0.0011(7) 0.0047(7) 0.0016(7) C5 0.0247(9) 0.0159(9) 0.0245(9) 0.0032(7) 0.0052(7) 0.0008(7) C6 0.0239(10) 0.0217(10) 0.0204(8) 0.0053(7) 0.0062(7) 0.0001(8) C7 0.0203(9) 0.0220(9) 0.0180(8) -0.0010(7) 0.0066(7) 0.0008(7) C8 0.0179(8) 0.0171(9) 0.0187(8) 0.0012(7) 0.0043(7) 0.0015(7) C9 0.0257(9) 0.0157(8) 0.0178(8) 0.0014(7) 0.0099(7) -0.0001(7) C10 0.0355(11) 0.0220(10) 0.0254(9) -0.0045(8) 0.0134(9) -0.0022(8) C11 0.0473(14) 0.0232(11) 0.0389(11) -0.0038(9) 0.0266(11) 0.0055(10) C12 0.0309(12) 0.0259(11) 0.0446(12) 0.0078(9) 0.0191(10) 0.0101(9) C13 0.0263(10) 0.0237(10) 0.0308(10) 0.0076(8) 0.0087(8) 0.0024(8) C14 0.0244(9) 0.0184(9) 0.0205(8) 0.0009(7) 0.0083(7) 0.0023(7) C15 0.0175(8) 0.0135(8) 0.0180(8) 0.0018(6) 0.0068(7) 0.0028(7) C16 0.0193(8) 0.0179(9) 0.0139(7) -0.0015(6) 0.0017(7) 0.0018(7) C17 0.0172(8) 0.0158(8) 0.0209(8) -0.0013(7) 0.0032(7) -0.0006(7) C18 0.0200(9) 0.0168(9) 0.0175(8) 0.0020(7) 0.0063(7) -0.0008(7) C19 0.0214(9) 0.0143(8) 0.0158(7) -0.0018(6) 0.0041(7) 0.0035(7) C20 0.0172(8) 0.0158(8) 0.0202(8) -0.0001(7) 0.0036(7) -0.0003(7) C21 0.0265(10) 0.0247(10) 0.0249(9) 0.0051(8) 0.0030(8) -0.0081(8) C22 0.0242(10) 0.0243(10) 0.0161(8) 0.0039(7) 0.0045(7) -0.0030(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 O1 C2 1.2243(19) . ? O2 C17 1.3706(19) . ? O2 C21 1.428(2) . ? O3 C19 1.3651(19) . ? O3 C22 1.428(2) . ? N1 C1 1.280(2) . ? N1 C15 1.420(2) . ? C1 C3 1.481(2) . ? C1 C2 1.521(2) . ? C2 C9 1.478(2) . ? C3 C4 1.394(2) . ? C3 C8 1.397(2) . ? C4 C5 1.387(2) . ? C4 H4 0.969(18) . ? C5 C6 1.387(3) . ? C5 H5 0.991(19) . ? C6 C7 1.385(3) . ? C6 H6 0.957(19) . ? C7 C8 1.381(2) . ? C7 H7 0.956(18) . ? C8 H8 0.99(2) . ? C9 C10 1.394(2) . ? C9 C14 1.395(2) . ? C10 C11 1.382(3) . ? C10 H10 1.004(17) . ? C11 C12 1.390(3) . ? C11 H11 0.92(2) . ? C12 C13 1.377(3) . ? C12 H12 0.94(2) . ? C13 C14 1.389(3) . ? C13 H13 0.99(2) . ? C14 H14 0.949(18) . ? C15 C16 1.391(2) . ? C15 C20 1.392(2) . ? C16 C17 1.380(2) . ? C16 H16 0.973(15) . ? C17 C18 1.391(2) . ? C18 C19 1.393(2) . ? C18 H18 0.954(17) . ? C19 C20 1.386(2) . ? C20 H20 0.967(18) . ? C21 H21A 0.996(19) . ? C21 H21B 1.02(2) . ? C21 H21C 1.01(2) . ? C22 H22A 0.946(18) . ? C22 H22B 1.01(2) . ? C22 H22C 0.977(19) . ? 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 O2 C21 117.51(13) . . ? C19 O3 C22 117.25(13) . . ? C1 N1 C15 123.05(14) . . ? N1 C1 C3 119.57(15) . . ? N1 C1 C2 124.76(15) . . ? C3 C1 C2 115.65(14) . . ? O1 C2 C9 123.18(15) . . ? O1 C2 C1 118.31(15) . . ? C9 C2 C1 118.45(14) . . ? C4 C3 C8 118.72(16) . . ? C4 C3 C1 121.16(15) . . ? C8 C3 C1 120.02(15) . . ? C5 C4 C3 121.01(17) . . ? C5 C4 H4 119.4(11) . . ? C3 C4 H4 119.6(11) . . ? C4 C5 C6 119.46(18) . . ? C4 C5 H5 121.2(10) . . ? C6 C5 H5 119.3(10) . . ? C7 C6 C5 120.09(17) . . ? C7 C6 H6 120.7(11) . . ? C5 C6 H6 119.2(11) . . ? C8 C7 C6 120.43(17) . . ? C8 C7 H7 117.7(11) . . ? C6 C7 H7 121.9(11) . . ? C7 C8 C3 120.28(17) . . ? C7 C8 H8 121.1(11) . . ? C3 C8 H8 118.7(11) . . ? C10 C9 C14 119.42(17) . . ? C10 C9 C2 119.91(16) . . ? C14 C9 C2 120.64(15) . . ? C11 C10 C9 119.96(18) . . ? C11 C10 H10 123.5(11) . . ? C9 C10 H10 116.6(11) . . ? C10 C11 C12 120.16(19) . . ? C10 C11 H11 121.2(14) . . ? C12 C11 H11 118.7(14) . . ? C13 C12 C11 120.4(2) . . ? C13 C12 H12 119.4(13) . . ? C11 C12 H12 120.2(13) . . ? C12 C13 C14 119.73(19) . . ? C12 C13 H13 121.7(12) . . ? C14 C13 H13 118.6(12) . . ? C13 C14 C9 120.34(17) . . ? C13 C14 H14 121.7(11) . . ? C9 C14 H14 117.9(11) . . ? C16 C15 C20 120.29(16) . . ? C16 C15 N1 116.08(14) . . ? C20 C15 N1 123.38(15) . . ? C17 C16 C15 119.68(15) . . ? C17 C16 H16 122.4(10) . . ? C15 C16 H16 118.0(10) . . ? O2 C17 C16 115.45(14) . . ? O2 C17 C18 123.26(15) . . ? C16 C17 C18 121.29(16) . . ? C17 C18 C19 118.10(16) . . ? C17 C18 H18 121.4(10) . . ? C19 C18 H18 120.5(10) . . ? O3 C19 C20 115.08(15) . . ? O3 C19 C18 123.26(15) . . ? C20 C19 C18 121.66(15) . . ? C19 C20 C15 118.97(16) . . ? C19 C20 H20 119.8(10) . . ? C15 C20 H20 121.0(10) . . ? O2 C21 H21A 107.2(11) . . ? O2 C21 H21B 111.7(12) . . ? H21A C21 H21B 108.9(16) . . ? O2 C21 H21C 110.0(12) . . ? H21A C21 H21C 107.9(15) . . ? H21B C21 H21C 111.0(15) . . ? O3 C22 H22A 105.8(12) . . ? O3 C22 H22B 110.1(11) . . ? H22A C22 H22B 110.7(15) . . ? O3 C22 H22C 109.1(10) . . ? H22A C22 H22C 109.9(15) . . ? H22B C22 H22C 111.1(15) . . ? 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 C15 N1 C1 C3 177.33(14) . . . . ? C15 N1 C1 C2 -1.0(2) . . . . ? N1 C1 C2 O1 -102.2(2) . . . . ? C3 C1 C2 O1 79.36(19) . . . . ? N1 C1 C2 C9 80.6(2) . . . . ? C3 C1 C2 C9 -97.83(18) . . . . ? N1 C1 C3 C4 -170.83(15) . . . . ? C2 C1 C3 C4 7.7(2) . . . . ? N1 C1 C3 C8 5.5(2) . . . . ? C2 C1 C3 C8 -176.01(15) . . . . ? C8 C3 C4 C5 -0.7(3) . . . . ? C1 C3 C4 C5 175.61(16) . . . . ? C3 C4 C5 C6 -0.2(3) . . . . ? C4 C5 C6 C7 1.0(3) . . . . ? C5 C6 C7 C8 -0.8(3) . . . . ? C6 C7 C8 C3 -0.1(3) . . . . ? C4 C3 C8 C7 0.9(3) . . . . ? C1 C3 C8 C7 -175.50(15) . . . . ? O1 C2 C9 C10 -2.1(3) . . . . ? C1 C2 C9 C10 174.93(16) . . . . ? O1 C2 C9 C14 179.85(16) . . . . ? C1 C2 C9 C14 -3.1(2) . . . . ? C14 C9 C10 C11 -0.3(3) . . . . ? C2 C9 C10 C11 -178.38(17) . . . . ? C9 C10 C11 C12 -0.4(3) . . . . ? C10 C11 C12 C13 0.8(3) . . . . ? C11 C12 C13 C14 -0.3(3) . . . . ? C12 C13 C14 C9 -0.4(3) . . . . ? C10 C9 C14 C13 0.8(3) . . . . ? C2 C9 C14 C13 178.81(16) . . . . ? C1 N1 C15 C16 -137.82(17) . . . . ? C1 N1 C15 C20 47.9(2) . . . . ? C20 C15 C16 C17 -1.0(3) . . . . ? N1 C15 C16 C17 -175.43(15) . . . . ? C21 O2 C17 C16 -173.86(16) . . . . ? C21 O2 C17 C18 5.5(2) . . . . ? C15 C16 C17 O2 -179.34(15) . . . . ? C15 C16 C17 C18 1.3(3) . . . . ? O2 C17 C18 C19 179.60(15) . . . . ? C16 C17 C18 C19 -1.1(3) . . . . ? C22 O3 C19 C20 171.22(16) . . . . ? C22 O3 C19 C18 -8.8(2) . . . . ? C17 C18 C19 O3 -179.43(16) . . . . ? C17 C18 C19 C20 0.6(2) . . . . ? O3 C19 C20 C15 179.68(15) . . . . ? C18 C19 C20 C15 -0.3(2) . . . . ? C16 C15 C20 C19 0.5(2) . . . . ? N1 C15 C20 C19 174.55(15) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 29.57 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.289 _refine_diff_density_min -0.249 _refine_diff_density_rms 0.053 _database_code_depnum_ccdc_archive 'CCDC 774004' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1-Pbca _vrf_PLAT094_jonjk66 ; PROBLEM: _C Ratio of Maximum / Minimum Residual Density .... 2.11 RESPONSE: The residual density lies in bonds (which are not modeled by SHELXL). ; _vrf_PLAT420_jonjk66 ; PROBLEM: _C D-H Without Acceptor N2 - H2 ... ? RESPONSE: The acceptor is atom O1, and the "bond" is intramolecular. ; _vrf_PLAT480_jonjk66 ; PROBLEM: _C Long H...A H-Bond Reported H1 .. O4 .. 2.69 Ang. Long H...A H-Bond Reported H2 .. O1 .. 2.61 Ang. RESPONSE: These weak "bonds" are intramolecular. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common jonjk66 _chemical_melting_point ? _chemical_formula_moiety 'C20 H24 N2 O4' _chemical_formula_sum 'C20 H24 N2 O4' _chemical_formula_weight 356.41 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 orthorhombic _symmetry_space_group_name_H-M 'P b c a' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 12.226(2) _cell_length_b 15.112(3) _cell_length_c 18.934(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3498.3(10) _cell_formula_units_Z 8 _cell_measurement_temperature 100.0(5) _cell_measurement_reflns_used 3990 _cell_measurement_theta_min 2.70 _cell_measurement_theta_max 33.59 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.353 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1520 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9649 _exptl_absorpt_correction_T_max 0.9850 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100.0(5) _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 II CCD Platform' _diffrn_measurement_method 'area detector, \w scans per \f' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 72057 _diffrn_reflns_av_R_equivalents 0.0924 _diffrn_reflns_av_sigmaI/netI 0.0492 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 34.97 _reflns_number_total 7695 _reflns_number_gt 4947 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2011)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction 'SAINT (Bruker, 2009)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0719P)^2^+0.2922P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7695 _refine_ls_number_parameters 331 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0914 _refine_ls_R_factor_gt 0.0527 _refine_ls_wR_factor_ref 0.1465 _refine_ls_wR_factor_gt 0.1255 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.72771(7) 0.09904(6) 0.29504(5) 0.02057(18) Uani 1 1 d . . . O2 O 0.96103(7) -0.11847(6) 0.39763(5) 0.02339(19) Uani 1 1 d . . . O3 O 0.78499(7) 0.41535(6) 0.57378(5) 0.0253(2) Uani 1 1 d . . . O4 O 1.13424(7) 0.33736(6) 0.46785(5) 0.02071(18) Uani 1 1 d . . . N1 N 1.07674(8) 0.18805(7) 0.35637(6) 0.01915(19) Uani 1 1 d . . . H1 H 1.1290(15) 0.1898(11) 0.3881(9) 0.031(4) Uiso 1 1 d . . . N2 N 0.81636(9) 0.28663(7) 0.34185(6) 0.01922(19) Uani 1 1 d . . . H2 H 0.7539(14) 0.2603(11) 0.3414(9) 0.027(4) Uiso 1 1 d . . . C1 C 1.01290(10) 0.26951(8) 0.34287(6) 0.0180(2) Uani 1 1 d . . . C2 C 0.90363(9) 0.23437(8) 0.30717(6) 0.0180(2) Uani 1 1 d . . . C3 C 0.90542(9) 0.13797(8) 0.32931(6) 0.0168(2) Uani 1 1 d . . . C4 C 1.00547(9) 0.11658(8) 0.35922(6) 0.0171(2) Uani 1 1 d . . . C5 C 0.85481(10) 0.31640(7) 0.40703(6) 0.0176(2) Uani 1 1 d . . . C6 C 0.96833(9) 0.31228(7) 0.40934(6) 0.0167(2) Uani 1 1 d . . . C7 C 1.08060(11) 0.33289(9) 0.29786(7) 0.0230(2) Uani 1 1 d . . . H7A H 1.1485(14) 0.3472(11) 0.3234(9) 0.026(4) Uiso 1 1 d . . . H7B H 1.0379(13) 0.3874(12) 0.2866(9) 0.029(4) Uiso 1 1 d . . . H7C H 1.1027(13) 0.3027(11) 0.2513(9) 0.027(4) Uiso 1 1 d . . . C8 C 0.89562(11) 0.24652(9) 0.22748(7) 0.0230(2) Uani 1 1 d . . . H8A H 0.8275(14) 0.2231(11) 0.2091(9) 0.030(4) Uiso 1 1 d . . . H8B H 0.9569(13) 0.2175(11) 0.2039(8) 0.022(4) Uiso 1 1 d . . . H8C H 0.8979(13) 0.3086(11) 0.2129(9) 0.025(4) Uiso 1 1 d . . . C9 C 0.82593(9) 0.07256(8) 0.32277(6) 0.0171(2) Uani 1 1 d . . . C10 C 0.84747(10) -0.01338(8) 0.34510(6) 0.0187(2) Uani 1 1 d . . . H10 H 0.7934(13) -0.0607(10) 0.3410(8) 0.023(4) Uiso 1 1 d . . . C11 C 0.94860(10) -0.03226(8) 0.37629(6) 0.0183(2) Uani 1 1 d . . . C12 C 1.02914(10) 0.03174(8) 0.38496(6) 0.0186(2) Uani 1 1 d . . . H12 H 1.0966(13) 0.0204(10) 0.4074(9) 0.021(4) Uiso 1 1 d . . . C13 C 0.64304(11) 0.03412(9) 0.29235(7) 0.0232(2) Uani 1 1 d . . . H13A H 0.5822(13) 0.0645(12) 0.2724(10) 0.030(4) Uiso 1 1 d . . . H13B H 0.6260(14) 0.0079(12) 0.3396(10) 0.033(5) Uiso 1 1 d . . . H13C H 0.6643(14) -0.0160(12) 0.2637(9) 0.033(4) Uiso 1 1 d . . . C14 C 1.05662(11) -0.13869(9) 0.43761(7) 0.0249(3) Uani 1 1 d . . . H14A H 1.0517(14) -0.2007(11) 0.4496(9) 0.027(4) Uiso 1 1 d . . . H14B H 1.0586(15) -0.1040(12) 0.4825(10) 0.037(5) Uiso 1 1 d . . . H14C H 1.1244(14) -0.1296(11) 0.4087(9) 0.027(4) Uiso 1 1 d . . . C15 C 0.79318(10) 0.35053(8) 0.46249(7) 0.0196(2) Uani 1 1 d . . . H15 H 0.7107(13) 0.3509(10) 0.4605(9) 0.024(4) Uiso 1 1 d . . . C16 C 0.85000(10) 0.38317(8) 0.52051(6) 0.0189(2) Uani 1 1 d . . . C17 C 0.96393(10) 0.38227(8) 0.52423(6) 0.0182(2) Uani 1 1 d . . . H17 H 1.0033(13) 0.4060(10) 0.5644(8) 0.021(4) Uiso 1 1 d . . . C18 C 1.02267(9) 0.34527(7) 0.46816(6) 0.0171(2) Uani 1 1 d . . . C19 C 0.83660(11) 0.46319(9) 0.62908(7) 0.0238(2) Uani 1 1 d . . . H19A H 0.7749(15) 0.4873(12) 0.6569(10) 0.037(5) Uiso 1 1 d . . . H19B H 0.8792(14) 0.5121(12) 0.6091(9) 0.030(4) Uiso 1 1 d . . . H19C H 0.8833(13) 0.4238(11) 0.6572(9) 0.024(4) Uiso 1 1 d . . . C20 C 1.19068(11) 0.36787(10) 0.52912(7) 0.0242(2) Uani 1 1 d . . . H20A H 1.2649(14) 0.3505(11) 0.5236(9) 0.026(4) Uiso 1 1 d . . . H20B H 1.1617(13) 0.3389(10) 0.5738(9) 0.024(4) Uiso 1 1 d . . . H20C H 1.1857(14) 0.4320(12) 0.5332(9) 0.030(4) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0185(4) 0.0201(4) 0.0231(4) 0.0009(3) -0.0045(3) -0.0007(3) O2 0.0225(4) 0.0171(4) 0.0305(5) 0.0047(3) -0.0002(4) 0.0019(3) O3 0.0209(4) 0.0317(5) 0.0233(4) -0.0085(4) 0.0035(3) 0.0019(4) O4 0.0163(4) 0.0261(4) 0.0198(4) -0.0030(3) -0.0002(3) -0.0007(3) N1 0.0165(4) 0.0172(4) 0.0237(5) -0.0019(4) 0.0001(4) -0.0001(3) N2 0.0193(5) 0.0183(4) 0.0200(5) -0.0014(4) -0.0031(4) 0.0012(4) C1 0.0197(5) 0.0166(5) 0.0179(5) -0.0005(4) 0.0011(4) -0.0007(4) C2 0.0208(5) 0.0168(5) 0.0166(5) -0.0001(4) -0.0002(4) 0.0001(4) C3 0.0189(5) 0.0167(5) 0.0149(5) -0.0006(4) 0.0001(4) 0.0003(4) C4 0.0181(5) 0.0171(5) 0.0162(5) -0.0020(4) 0.0017(4) 0.0000(4) C5 0.0190(5) 0.0154(5) 0.0184(5) 0.0008(4) -0.0010(4) 0.0005(4) C6 0.0180(5) 0.0145(4) 0.0178(5) 0.0001(4) 0.0008(4) 0.0005(4) C7 0.0273(6) 0.0206(5) 0.0211(5) -0.0003(4) 0.0056(5) -0.0045(5) C8 0.0301(6) 0.0220(5) 0.0169(5) 0.0007(4) -0.0017(5) -0.0020(5) C9 0.0175(5) 0.0189(5) 0.0149(5) -0.0016(4) -0.0007(4) 0.0004(4) C10 0.0191(5) 0.0170(5) 0.0200(5) -0.0004(4) 0.0009(4) -0.0012(4) C11 0.0201(5) 0.0158(5) 0.0190(5) 0.0018(4) 0.0027(4) 0.0015(4) C12 0.0177(5) 0.0189(5) 0.0192(5) -0.0003(4) 0.0007(4) 0.0020(4) C13 0.0200(5) 0.0264(6) 0.0233(6) -0.0010(5) -0.0029(5) -0.0044(5) C14 0.0256(6) 0.0232(6) 0.0257(6) 0.0042(5) -0.0014(5) 0.0048(5) C15 0.0178(5) 0.0190(5) 0.0221(5) -0.0008(4) 0.0001(4) 0.0018(4) C16 0.0197(5) 0.0171(5) 0.0197(5) -0.0011(4) 0.0030(4) 0.0014(4) C17 0.0187(5) 0.0185(5) 0.0175(5) -0.0016(4) 0.0006(4) -0.0004(4) C18 0.0166(5) 0.0163(5) 0.0183(5) 0.0018(4) 0.0003(4) -0.0010(4) C19 0.0260(6) 0.0251(6) 0.0205(6) -0.0035(5) 0.0021(5) 0.0003(5) C20 0.0189(5) 0.0311(7) 0.0227(6) -0.0041(5) -0.0031(4) -0.0001(5) _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 C9 1.3704(14) . ? O1 C13 1.4271(15) . ? O2 C11 1.3724(14) . ? O2 C14 1.4256(16) . ? O3 C16 1.3732(14) . ? O3 C19 1.4202(16) . ? O4 C18 1.3693(14) . ? O4 C20 1.4264(16) . ? N1 C4 1.3889(15) . ? N1 C1 1.4798(16) . ? N1 H1 0.878(19) . ? N2 C5 1.3952(15) . ? N2 C2 1.4810(16) . ? N2 H2 0.862(17) . ? C1 C6 1.5162(16) . ? C1 C7 1.5260(17) . ? C1 C2 1.5885(16) . ? C2 C3 1.5161(17) . ? C2 C8 1.5231(17) . ? C3 C4 1.3862(16) . ? C3 C9 1.3917(16) . ? C4 C12 1.4017(17) . ? C5 C6 1.3900(17) . ? C5 C15 1.3916(17) . ? C6 C18 1.3892(16) . ? C7 H7A 0.985(17) . ? C7 H7B 0.999(17) . ? C7 H7C 1.029(17) . ? C8 H8A 0.969(17) . ? C8 H8B 0.976(16) . ? C8 H8C 0.978(17) . ? C9 C10 1.3909(16) . ? C10 C11 1.3997(17) . ? C10 H10 0.977(16) . ? C11 C12 1.3900(17) . ? C12 H12 0.943(16) . ? C13 H13A 0.952(17) . ? C13 H13B 1.000(19) . ? C13 H13C 0.967(18) . ? C14 H14A 0.967(17) . ? C14 H14B 0.999(19) . ? C14 H14C 1.003(17) . ? C15 C16 1.3901(17) . ? C15 H15 1.010(16) . ? C16 C17 1.3949(17) . ? C17 C18 1.3984(16) . ? C17 H17 0.969(15) . ? C19 H19A 0.989(19) . ? C19 H19B 0.980(18) . ? C19 H19C 0.982(17) . ? C20 H20A 0.950(17) . ? C20 H20B 1.017(17) . ? C20 H20C 0.974(18) . ? 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 C9 O1 C13 116.66(10) . . ? C11 O2 C14 116.78(10) . . ? C16 O3 C19 117.68(10) . . ? C18 O4 C20 116.76(9) . . ? C4 N1 C1 108.82(9) . . ? C4 N1 H1 117.0(11) . . ? C1 N1 H1 118.5(11) . . ? C5 N2 C2 108.74(9) . . ? C5 N2 H2 117.2(11) . . ? C2 N2 H2 112.8(11) . . ? N1 C1 C6 113.62(10) . . ? N1 C1 C7 109.42(10) . . ? C6 C1 C7 113.01(10) . . ? N1 C1 C2 103.84(9) . . ? C6 C1 C2 101.15(9) . . ? C7 C1 C2 115.36(10) . . ? N2 C2 C3 113.59(10) . . ? N2 C2 C8 109.18(10) . . ? C3 C2 C8 112.99(10) . . ? N2 C2 C1 103.83(9) . . ? C3 C2 C1 101.04(9) . . ? C8 C2 C1 115.80(10) . . ? C4 C3 C9 119.14(11) . . ? C4 C3 C2 110.47(10) . . ? C9 C3 C2 130.38(10) . . ? C3 C4 N1 110.88(10) . . ? C3 C4 C12 122.51(11) . . ? N1 C4 C12 126.53(11) . . ? C6 C5 C15 122.24(11) . . ? C6 C5 N2 110.48(10) . . ? C15 C5 N2 127.20(11) . . ? C18 C6 C5 119.12(11) . . ? C18 C6 C1 130.28(11) . . ? C5 C6 C1 110.60(10) . . ? C1 C7 H7A 108.7(9) . . ? C1 C7 H7B 110.7(10) . . ? H7A C7 H7B 111.4(14) . . ? C1 C7 H7C 110.0(9) . . ? H7A C7 H7C 107.3(13) . . ? H7B C7 H7C 108.7(13) . . ? C2 C8 H8A 111.5(10) . . ? C2 C8 H8B 110.5(9) . . ? H8A C8 H8B 109.4(14) . . ? C2 C8 H8C 113.2(10) . . ? H8A C8 H8C 105.9(14) . . ? H8B C8 H8C 106.2(13) . . ? O1 C9 C10 123.71(10) . . ? O1 C9 C3 116.02(10) . . ? C10 C9 C3 120.26(11) . . ? C9 C10 C11 119.07(11) . . ? C9 C10 H10 122.1(9) . . ? C11 C10 H10 118.8(9) . . ? O2 C11 C12 123.18(11) . . ? O2 C11 C10 114.55(10) . . ? C12 C11 C10 122.26(11) . . ? C11 C12 C4 116.69(11) . . ? C11 C12 H12 123.1(10) . . ? C4 C12 H12 120.2(10) . . ? O1 C13 H13A 104.4(10) . . ? O1 C13 H13B 113.1(10) . . ? H13A C13 H13B 112.5(14) . . ? O1 C13 H13C 111.3(10) . . ? H13A C13 H13C 111.5(15) . . ? H13B C13 H13C 104.2(14) . . ? O2 C14 H14A 106.4(10) . . ? O2 C14 H14B 111.1(11) . . ? H14A C14 H14B 108.1(15) . . ? O2 C14 H14C 111.0(10) . . ? H14A C14 H14C 108.2(14) . . ? H14B C14 H14C 111.9(15) . . ? C16 C15 C5 117.20(11) . . ? C16 C15 H15 121.8(9) . . ? C5 C15 H15 121.0(10) . . ? O3 C16 C15 114.63(11) . . ? O3 C16 C17 122.98(11) . . ? C15 C16 C17 122.38(11) . . ? C16 C17 C18 118.58(11) . . ? C16 C17 H17 122.2(9) . . ? C18 C17 H17 119.2(9) . . ? O4 C18 C6 116.21(10) . . ? O4 C18 C17 123.35(10) . . ? C6 C18 C17 120.43(11) . . ? O3 C19 H19A 103.9(11) . . ? O3 C19 H19B 109.6(10) . . ? H19A C19 H19B 109.5(15) . . ? O3 C19 H19C 110.5(9) . . ? H19A C19 H19C 112.1(15) . . ? H19B C19 H19C 110.9(14) . . ? O4 C20 H20A 106.4(10) . . ? O4 C20 H20B 111.7(9) . . ? H20A C20 H20B 107.8(13) . . ? O4 C20 H20C 110.9(10) . . ? H20A C20 H20C 110.1(14) . . ? H20B C20 H20C 109.9(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 C4 N1 C1 C6 86.33(12) . . . . ? C4 N1 C1 C7 -146.32(10) . . . . ? C4 N1 C1 C2 -22.64(12) . . . . ? C5 N2 C2 C3 85.49(12) . . . . ? C5 N2 C2 C8 -147.41(10) . . . . ? C5 N2 C2 C1 -23.33(12) . . . . ? N1 C1 C2 N2 137.03(9) . . . . ? C6 C1 C2 N2 19.04(11) . . . . ? C7 C1 C2 N2 -103.26(11) . . . . ? N1 C1 C2 C3 19.12(11) . . . . ? C6 C1 C2 C3 -98.86(10) . . . . ? C7 C1 C2 C3 138.84(10) . . . . ? N1 C1 C2 C8 -103.31(11) . . . . ? C6 C1 C2 C8 138.70(10) . . . . ? C7 C1 C2 C8 16.40(15) . . . . ? N2 C2 C3 C4 -120.76(11) . . . . ? C8 C2 C3 C4 114.16(12) . . . . ? C1 C2 C3 C4 -10.21(12) . . . . ? N2 C2 C3 C9 60.46(16) . . . . ? C8 C2 C3 C9 -64.62(16) . . . . ? C1 C2 C3 C9 171.01(12) . . . . ? C9 C3 C4 N1 175.44(10) . . . . ? C2 C3 C4 N1 -3.50(13) . . . . ? C9 C3 C4 C12 -1.65(17) . . . . ? C2 C3 C4 C12 179.41(10) . . . . ? C1 N1 C4 C3 17.14(13) . . . . ? C1 N1 C4 C12 -165.92(11) . . . . ? C2 N2 C5 C6 18.41(13) . . . . ? C2 N2 C5 C15 -164.83(11) . . . . ? C15 C5 C6 C18 -1.63(17) . . . . ? N2 C5 C6 C18 175.32(10) . . . . ? C15 C5 C6 C1 178.18(10) . . . . ? N2 C5 C6 C1 -4.87(13) . . . . ? N1 C1 C6 C18 59.82(16) . . . . ? C7 C1 C6 C18 -65.63(16) . . . . ? C2 C1 C6 C18 170.44(12) . . . . ? N1 C1 C6 C5 -119.97(11) . . . . ? C7 C1 C6 C5 114.58(11) . . . . ? C2 C1 C6 C5 -9.34(12) . . . . ? C13 O1 C9 C10 2.66(16) . . . . ? C13 O1 C9 C3 -175.97(10) . . . . ? C4 C3 C9 O1 177.78(10) . . . . ? C2 C3 C9 O1 -3.53(18) . . . . ? C4 C3 C9 C10 -0.91(17) . . . . ? C2 C3 C9 C10 177.79(11) . . . . ? O1 C9 C10 C11 -176.46(11) . . . . ? C3 C9 C10 C11 2.12(17) . . . . ? C14 O2 C11 C12 7.41(17) . . . . ? C14 O2 C11 C10 -172.33(11) . . . . ? C9 C10 C11 O2 178.88(10) . . . . ? C9 C10 C11 C12 -0.87(18) . . . . ? O2 C11 C12 C4 178.74(11) . . . . ? C10 C11 C12 C4 -1.53(17) . . . . ? C3 C4 C12 C11 2.82(17) . . . . ? N1 C4 C12 C11 -173.79(11) . . . . ? C6 C5 C15 C16 1.74(17) . . . . ? N2 C5 C15 C16 -174.67(11) . . . . ? C19 O3 C16 C15 -169.52(11) . . . . ? C19 O3 C16 C17 11.09(17) . . . . ? C5 C15 C16 O3 -179.53(10) . . . . ? C5 C15 C16 C17 -0.14(18) . . . . ? O3 C16 C17 C18 177.83(11) . . . . ? C15 C16 C17 C18 -1.51(18) . . . . ? C20 O4 C18 C6 -177.66(11) . . . . ? C20 O4 C18 C17 0.96(16) . . . . ? C5 C6 C18 O4 178.54(10) . . . . ? C1 C6 C18 O4 -1.23(17) . . . . ? C5 C6 C18 C17 -0.12(17) . . . . ? C1 C6 C18 C17 -179.88(11) . . . . ? C16 C17 C18 O4 -176.93(11) . . . . ? C16 C17 C18 C6 1.63(17) . . . . ? 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 O4 0.878(19) 2.694(17) 3.1685(14) 115.2(14) . N1 H1 O3 0.878(19) 2.585(18) 3.2670(15) 135.2(14) 4_556 N2 H2 O1 0.862(17) 2.609(17) 3.1618(14) 122.9(14) . #N2 H2 O2 0.862(17) 3.376(17) 3.8307(15) 115.9(13) 8_765 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 34.97 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.502 _refine_diff_density_min -0.238 _refine_diff_density_rms 0.064 _database_code_depnum_ccdc_archive 'CCDC 937917' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_3-P-1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common jonjk59 _chemical_melting_point ? _chemical_formula_moiety 'C22 H19 N O3' _chemical_formula_sum 'C22 H19 N O3' _chemical_formula_weight 345.38 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 9.9208(19) _cell_length_b 13.015(3) _cell_length_c 13.699(3) _cell_angle_alpha 78.473(4) _cell_angle_beta 82.317(4) _cell_angle_gamma 83.248(4) _cell_volume 1710.0(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100.0(1) _cell_measurement_reflns_used 4077 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 35.00 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.342 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9771 _exptl_absorpt_correction_T_max 0.9841 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100.0(1) _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 II CCD Platform' _diffrn_measurement_method 'area detector, \w scans per \f' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 37134 _diffrn_reflns_av_R_equivalents 0.0768 _diffrn_reflns_av_sigmaI/netI 0.1053 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 34.97 _reflns_number_total 14795 _reflns_number_gt 8102 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2011)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction 'SAINT (Bruker, 2009)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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. The amine hydrogen atoms were found from the difference Fourier map, and their positional and isotropic displacement parameters were refined independently from those of all other atoms. ; _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^)+(0.0632P)^2^+0.0000P] 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 14795 _refine_ls_number_parameters 477 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1231 _refine_ls_R_factor_gt 0.0620 _refine_ls_wR_factor_ref 0.1631 _refine_ls_wR_factor_gt 0.1337 _refine_ls_goodness_of_fit_ref 0.992 _refine_ls_restrained_S_all 0.992 _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 0.06232(11) 0.43701(9) 0.36993(8) 0.0199(2) Uani 1 1 d . . . O2 O -0.08441(11) 0.31809(9) 0.09650(9) 0.0249(2) Uani 1 1 d . . . O3 O 0.51503(11) 0.55925(8) 0.10957(8) 0.0186(2) Uani 1 1 d . . . N1 N 0.33586(13) 0.48887(10) 0.06572(9) 0.0169(2) Uani 1 1 d . . . H1 H 0.375(2) 0.4799(15) 0.0055(15) 0.031(5) Uiso 1 1 d . . . C1 C 0.40327(14) 0.52382(11) 0.13017(10) 0.0156(3) Uani 1 1 d . . . C2 C 0.31756(14) 0.50944(11) 0.23460(10) 0.0146(3) Uani 1 1 d . . . C3 C 0.19594(14) 0.46013(11) 0.21329(10) 0.0147(3) Uani 1 1 d . . . C4 C 0.21457(14) 0.44785(11) 0.11404(11) 0.0158(3) Uani 1 1 d . . . C7 C 0.40395(14) 0.43280(11) 0.30797(11) 0.0155(3) Uani 1 1 d . . . C8 C 0.28830(14) 0.61820(11) 0.26294(10) 0.0145(3) Uani 1 1 d . . . C9 C 0.07901(14) 0.42345(11) 0.27254(11) 0.0161(3) Uani 1 1 d . . . C10 C -0.01341(15) 0.37624(12) 0.23061(11) 0.0184(3) Uani 1 1 d . . . H10 H -0.0928 0.3510 0.2707 0.022 Uiso 1 1 calc R . . C11 C 0.01108(15) 0.36620(12) 0.12987(11) 0.0186(3) Uani 1 1 d . . . C12 C 0.12598(15) 0.40280(12) 0.06889(11) 0.0186(3) Uani 1 1 d . . . H12 H 0.1425 0.3971 0.0002 0.022 Uiso 1 1 calc R . . C13 C -0.05289(16) 0.39485(13) 0.43361(12) 0.0218(3) Uani 1 1 d . . . H13A H -0.0535 0.4100 0.5009 0.033 Uiso 1 1 calc R . . H13B H -0.0466 0.3185 0.4374 0.033 Uiso 1 1 calc R . . H13C H -0.1373 0.4273 0.4060 0.033 Uiso 1 1 calc R . . C14 C -0.05337(17) 0.29717(14) -0.00325(12) 0.0251(3) Uani 1 1 d . . . H14A H -0.1283 0.2633 -0.0198 0.038 Uiso 1 1 calc R . . H14B H 0.0313 0.2504 -0.0075 0.038 Uiso 1 1 calc R . . H14C H -0.0419 0.3635 -0.0507 0.038 Uiso 1 1 calc R . . C15 C 0.50031(16) 0.35759(12) 0.27395(12) 0.0216(3) Uani 1 1 d . . . H15 H 0.5103 0.3517 0.2053 0.026 Uiso 1 1 calc R . . C16 C 0.58209(18) 0.29100(13) 0.33903(12) 0.0256(3) Uani 1 1 d . . . H16 H 0.6481 0.2404 0.3146 0.031 Uiso 1 1 calc R . . C17 C 0.56795(17) 0.29798(13) 0.43919(12) 0.0238(3) Uani 1 1 d . . . H17 H 0.6250 0.2532 0.4836 0.029 Uiso 1 1 calc R . . C18 C 0.47001(17) 0.37071(13) 0.47445(12) 0.0227(3) Uani 1 1 d . . . H18 H 0.4585 0.3749 0.5436 0.027 Uiso 1 1 calc R . . C19 C 0.38851(16) 0.43760(12) 0.40925(11) 0.0193(3) Uani 1 1 d . . . H19 H 0.3214 0.4872 0.4342 0.023 Uiso 1 1 calc R . . C20 C 0.39779(15) 0.66750(11) 0.28083(11) 0.0165(3) Uani 1 1 d . . . H20 H 0.4873 0.6323 0.2765 0.020 Uiso 1 1 calc R . . C21 C 0.37758(16) 0.76697(12) 0.30474(11) 0.0192(3) Uani 1 1 d . . . H21 H 0.4530 0.7995 0.3170 0.023 Uiso 1 1 calc R . . C22 C 0.24762(16) 0.81929(12) 0.31085(12) 0.0214(3) Uani 1 1 d . . . H22 H 0.2336 0.8873 0.3280 0.026 Uiso 1 1 calc R . . C23 C 0.13826(16) 0.77193(12) 0.29190(13) 0.0236(3) Uani 1 1 d . . . H23 H 0.0493 0.8081 0.2949 0.028 Uiso 1 1 calc R . . C24 C 0.15829(15) 0.67135(12) 0.26839(11) 0.0194(3) Uani 1 1 d . . . H24 H 0.0828 0.6391 0.2561 0.023 Uiso 1 1 calc R . . O4 O 0.97522(10) 0.00366(9) 0.14777(8) 0.0214(2) Uani 1 1 d . . . O5 O 1.11785(11) 0.15282(9) 0.41195(8) 0.0212(2) Uani 1 1 d . . . O6 O 0.49258(10) -0.04092(8) 0.38651(8) 0.0177(2) Uani 1 1 d . . . N2 N 0.67316(12) 0.02988(10) 0.42961(9) 0.0153(2) Uani 1 1 d . . . H2 H 0.633(2) 0.0420(15) 0.4905(15) 0.028(5) Uiso 1 1 d . . . C31 C 0.60811(14) -0.01226(11) 0.36805(10) 0.0147(3) Uani 1 1 d . . . C32 C 0.70496(14) -0.01917(11) 0.26996(10) 0.0149(3) Uani 1 1 d . . . C33 C 0.83000(14) 0.02337(11) 0.29298(10) 0.0148(3) Uani 1 1 d . . . C34 C 0.80605(14) 0.05218(11) 0.38673(10) 0.0147(3) Uani 1 1 d . . . C37 C 0.73315(14) -0.13584(11) 0.26216(11) 0.0159(3) Uani 1 1 d . . . C38 C 0.63384(14) 0.05199(11) 0.18442(10) 0.0155(3) Uani 1 1 d . . . C39 C 0.95710(14) 0.03558(11) 0.23797(10) 0.0160(3) Uani 1 1 d . . . C40 C 1.05660(14) 0.07952(11) 0.27605(11) 0.0171(3) Uani 1 1 d . . . H40 H 1.1434 0.0889 0.2385 0.021 Uiso 1 1 calc R . . C41 C 1.02737(14) 0.10939(11) 0.36933(11) 0.0166(3) Uani 1 1 d . . . C42 C 0.90103(15) 0.09526(11) 0.42733(11) 0.0167(3) Uani 1 1 d . . . H42 H 0.8818 0.1144 0.4915 0.020 Uiso 1 1 calc R . . C43 C 1.10820(15) 0.00760(14) 0.09281(12) 0.0248(3) Uani 1 1 d . . . H43A H 1.1080 -0.0174 0.0299 0.037 Uiso 1 1 calc R . . H43B H 1.1749 -0.0374 0.1329 0.037 Uiso 1 1 calc R . . H43C H 1.1328 0.0803 0.0779 0.037 Uiso 1 1 calc R . . C44 C 1.24727(15) 0.17388(13) 0.35510(13) 0.0236(3) Uani 1 1 d . . . H44A H 1.3017 0.2052 0.3941 0.035 Uiso 1 1 calc R . . H44B H 1.2325 0.2229 0.2923 0.035 Uiso 1 1 calc R . . H44C H 1.2960 0.1079 0.3400 0.035 Uiso 1 1 calc R . . C45 C 0.77120(16) -0.20794(12) 0.34641(12) 0.0210(3) Uani 1 1 d . . . H45 H 0.7797 -0.1835 0.4060 0.025 Uiso 1 1 calc R . . C46 C 0.79666(16) -0.31443(13) 0.34432(13) 0.0251(3) Uani 1 1 d . . . H46 H 0.8231 -0.3622 0.4021 0.030 Uiso 1 1 calc R . . C47 C 0.78384(16) -0.35164(13) 0.25856(13) 0.0253(3) Uani 1 1 d . . . H47 H 0.8005 -0.4248 0.2573 0.030 Uiso 1 1 calc R . . C48 C 0.74653(17) -0.28116(14) 0.17460(13) 0.0257(3) Uani 1 1 d . . . H48 H 0.7364 -0.3062 0.1157 0.031 Uiso 1 1 calc R . . C49 C 0.72373(16) -0.17369(13) 0.17574(12) 0.0210(3) Uani 1 1 d . . . H49 H 0.7015 -0.1259 0.1168 0.025 Uiso 1 1 calc R . . C50 C 0.51525(15) 0.02386(12) 0.15623(11) 0.0198(3) Uani 1 1 d . . . H50 H 0.4799 -0.0406 0.1886 0.024 Uiso 1 1 calc R . . C51 C 0.44871(16) 0.08980(14) 0.08095(12) 0.0251(3) Uani 1 1 d . . . H51 H 0.3693 0.0692 0.0612 0.030 Uiso 1 1 calc R . . C52 C 0.49684(17) 0.18537(13) 0.03433(12) 0.0256(3) Uani 1 1 d . . . H52 H 0.4510 0.2301 -0.0171 0.031 Uiso 1 1 calc R . . C53 C 0.61209(16) 0.21445(13) 0.06368(12) 0.0231(3) Uani 1 1 d . . . H53 H 0.6446 0.2805 0.0332 0.028 Uiso 1 1 calc R . . C54 C 0.68121(15) 0.14823(12) 0.13739(11) 0.0189(3) Uani 1 1 d . . . H54 H 0.7616 0.1688 0.1559 0.023 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 O1 0.0204(5) 0.0242(6) 0.0154(5) -0.0045(4) 0.0029(4) -0.0083(4) O2 0.0215(6) 0.0334(6) 0.0242(6) -0.0106(5) -0.0011(4) -0.0127(5) O3 0.0173(5) 0.0214(5) 0.0175(5) -0.0043(4) 0.0005(4) -0.0058(4) N1 0.0177(6) 0.0209(6) 0.0127(5) -0.0044(5) 0.0013(4) -0.0054(5) C1 0.0160(6) 0.0160(6) 0.0145(6) -0.0030(5) -0.0014(5) -0.0007(5) C2 0.0149(6) 0.0150(6) 0.0136(6) -0.0017(5) -0.0008(5) -0.0030(5) C3 0.0138(6) 0.0153(6) 0.0157(6) -0.0036(5) -0.0011(5) -0.0031(5) C4 0.0145(6) 0.0158(6) 0.0171(6) -0.0035(5) 0.0001(5) -0.0029(5) C7 0.0157(6) 0.0144(6) 0.0168(6) -0.0029(5) -0.0021(5) -0.0033(5) C8 0.0168(6) 0.0134(6) 0.0129(6) -0.0010(5) -0.0011(5) -0.0026(5) C9 0.0165(6) 0.0163(6) 0.0150(6) -0.0027(5) 0.0010(5) -0.0027(5) C10 0.0158(6) 0.0188(7) 0.0206(7) -0.0037(6) 0.0007(5) -0.0050(5) C11 0.0167(7) 0.0191(7) 0.0218(7) -0.0060(6) -0.0031(5) -0.0040(5) C12 0.0194(7) 0.0203(7) 0.0176(7) -0.0055(6) -0.0016(5) -0.0052(5) C13 0.0209(7) 0.0236(8) 0.0200(7) -0.0038(6) 0.0060(6) -0.0074(6) C14 0.0236(8) 0.0309(9) 0.0244(8) -0.0105(7) -0.0029(6) -0.0080(6) C15 0.0246(8) 0.0203(7) 0.0186(7) -0.0037(6) -0.0019(6) 0.0027(6) C16 0.0292(8) 0.0204(8) 0.0247(8) -0.0031(6) -0.0024(6) 0.0055(6) C17 0.0245(8) 0.0212(8) 0.0242(8) 0.0002(6) -0.0078(6) 0.0014(6) C18 0.0273(8) 0.0221(8) 0.0185(7) -0.0031(6) -0.0036(6) -0.0005(6) C19 0.0204(7) 0.0187(7) 0.0179(7) -0.0038(5) -0.0008(5) 0.0002(5) C20 0.0161(6) 0.0164(7) 0.0173(6) -0.0029(5) -0.0024(5) -0.0019(5) C21 0.0216(7) 0.0184(7) 0.0183(7) -0.0031(5) -0.0025(5) -0.0054(5) C22 0.0274(8) 0.0152(7) 0.0216(7) -0.0038(6) -0.0018(6) -0.0016(6) C23 0.0202(7) 0.0187(7) 0.0305(9) -0.0041(6) -0.0019(6) 0.0021(6) C24 0.0167(7) 0.0190(7) 0.0219(7) -0.0025(6) -0.0019(5) -0.0020(5) O4 0.0150(5) 0.0341(6) 0.0162(5) -0.0080(4) 0.0019(4) -0.0047(4) O5 0.0177(5) 0.0234(6) 0.0251(6) -0.0066(5) -0.0040(4) -0.0065(4) O6 0.0148(5) 0.0205(5) 0.0178(5) -0.0041(4) 0.0012(4) -0.0042(4) N2 0.0143(5) 0.0181(6) 0.0132(5) -0.0038(4) 0.0013(4) -0.0025(4) C31 0.0150(6) 0.0129(6) 0.0153(6) -0.0014(5) -0.0003(5) -0.0014(5) C32 0.0135(6) 0.0175(6) 0.0139(6) -0.0032(5) -0.0003(5) -0.0029(5) C33 0.0127(6) 0.0165(6) 0.0149(6) -0.0020(5) -0.0010(5) -0.0025(5) C34 0.0143(6) 0.0139(6) 0.0149(6) -0.0009(5) -0.0020(5) -0.0006(5) C37 0.0116(6) 0.0184(7) 0.0179(7) -0.0052(5) 0.0015(5) -0.0023(5) C38 0.0154(6) 0.0176(7) 0.0132(6) -0.0025(5) -0.0011(5) -0.0017(5) C39 0.0145(6) 0.0180(7) 0.0149(6) -0.0020(5) -0.0007(5) -0.0020(5) C40 0.0133(6) 0.0182(7) 0.0186(7) -0.0001(5) -0.0007(5) -0.0027(5) C41 0.0146(6) 0.0148(6) 0.0207(7) -0.0016(5) -0.0060(5) -0.0018(5) C42 0.0178(6) 0.0160(6) 0.0168(7) -0.0031(5) -0.0038(5) -0.0018(5) C43 0.0144(7) 0.0394(10) 0.0186(7) -0.0040(7) 0.0026(5) -0.0016(6) C44 0.0150(7) 0.0261(8) 0.0302(9) -0.0036(7) -0.0034(6) -0.0060(6) C45 0.0213(7) 0.0211(7) 0.0200(7) -0.0033(6) -0.0021(6) -0.0008(6) C46 0.0226(8) 0.0197(7) 0.0303(9) -0.0012(6) -0.0014(6) 0.0015(6) C47 0.0192(7) 0.0186(7) 0.0386(10) -0.0099(7) 0.0008(6) -0.0003(6) C48 0.0216(8) 0.0279(9) 0.0305(9) -0.0149(7) -0.0024(6) 0.0016(6) C49 0.0208(7) 0.0245(8) 0.0185(7) -0.0075(6) -0.0019(5) 0.0001(6) C50 0.0182(7) 0.0209(7) 0.0199(7) -0.0004(6) -0.0031(5) -0.0051(6) C51 0.0183(7) 0.0315(9) 0.0249(8) 0.0020(7) -0.0083(6) -0.0061(6) C52 0.0228(8) 0.0274(8) 0.0233(8) 0.0055(6) -0.0069(6) -0.0015(6) C53 0.0231(8) 0.0203(7) 0.0244(8) 0.0019(6) -0.0041(6) -0.0041(6) C54 0.0157(7) 0.0201(7) 0.0207(7) -0.0016(6) -0.0030(5) -0.0032(5) _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 C9 1.3663(17) . ? O1 C13 1.4346(17) . ? O2 C11 1.3668(18) . ? O2 C14 1.433(2) . ? O3 C1 1.2272(17) . ? N1 C1 1.3504(19) . ? N1 C4 1.4029(18) . ? N1 H1 0.89(2) . ? C1 C2 1.552(2) . ? C2 C3 1.5179(19) . ? C2 C8 1.527(2) . ? C2 C7 1.539(2) . ? C3 C4 1.386(2) . ? C3 C9 1.3986(19) . ? C4 C12 1.382(2) . ? C7 C19 1.388(2) . ? C7 C15 1.390(2) . ? C8 C24 1.390(2) . ? C8 C20 1.396(2) . ? C9 C10 1.401(2) . ? C10 C11 1.398(2) . ? C10 H10 0.9500 . ? C11 C12 1.392(2) . ? C12 H12 0.9500 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C16 1.387(2) . ? C15 H15 0.9500 . ? C16 C17 1.381(2) . ? C16 H16 0.9500 . ? C17 C18 1.384(2) . ? C17 H17 0.9500 . ? C18 C19 1.388(2) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 C21 1.384(2) . ? C20 H20 0.9500 . ? C21 C22 1.386(2) . ? C21 H21 0.9500 . ? C22 C23 1.386(2) . ? C22 H22 0.9500 . ? C23 C24 1.395(2) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? O4 C39 1.3639(17) . ? O4 C43 1.4300(18) . ? O5 C41 1.3629(17) . ? O5 C44 1.4354(18) . ? O6 C31 1.2256(17) . ? N2 C31 1.3572(19) . ? N2 C34 1.4080(18) . ? N2 H2 0.909(19) . ? C31 C32 1.5556(19) . ? C32 C33 1.5102(19) . ? C32 C37 1.534(2) . ? C32 C38 1.537(2) . ? C33 C39 1.3886(19) . ? C33 C34 1.391(2) . ? C34 C42 1.379(2) . ? C37 C49 1.388(2) . ? C37 C45 1.398(2) . ? C38 C54 1.393(2) . ? C38 C50 1.395(2) . ? C39 C40 1.401(2) . ? C40 C41 1.393(2) . ? C40 H40 0.9500 . ? C41 C42 1.402(2) . ? C42 H42 0.9500 . ? C43 H43A 0.9800 . ? C43 H43B 0.9800 . ? C43 H43C 0.9800 . ? C44 H44A 0.9800 . ? C44 H44B 0.9800 . ? C44 H44C 0.9800 . ? C45 C46 1.385(2) . ? C45 H45 0.9500 . ? C46 C47 1.383(2) . ? C46 H46 0.9500 . ? C47 C48 1.383(2) . ? C47 H47 0.9500 . ? C48 C49 1.393(2) . ? C48 H48 0.9500 . ? C49 H49 0.9500 . ? C50 C51 1.390(2) . ? C50 H50 0.9500 . ? C51 C52 1.387(2) . ? C51 H51 0.9500 . ? C52 C53 1.378(2) . ? C52 H52 0.9500 . ? C53 C54 1.390(2) . ? C53 H53 0.9500 . ? C54 H54 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 O1 C13 117.48(12) . . ? C11 O2 C14 116.09(12) . . ? C1 N1 C4 111.24(12) . . ? C1 N1 H1 122.0(13) . . ? C4 N1 H1 125.3(13) . . ? O3 C1 N1 125.36(13) . . ? O3 C1 C2 125.88(13) . . ? N1 C1 C2 108.75(12) . . ? C3 C2 C8 116.49(12) . . ? C3 C2 C7 112.05(11) . . ? C8 C2 C7 112.03(11) . . ? C3 C2 C1 100.98(11) . . ? C8 C2 C1 106.99(11) . . ? C7 C2 C1 107.13(11) . . ? C4 C3 C9 117.52(13) . . ? C4 C3 C2 108.89(12) . . ? C9 C3 C2 133.54(13) . . ? C12 C4 C3 125.03(13) . . ? C12 C4 N1 124.90(13) . . ? C3 C4 N1 110.06(12) . . ? C19 C7 C15 118.47(14) . . ? C19 C7 C2 120.97(13) . . ? C15 C7 C2 120.56(13) . . ? C24 C8 C20 118.83(13) . . ? C24 C8 C2 122.78(13) . . ? C20 C8 C2 118.36(12) . . ? O1 C9 C3 116.49(13) . . ? O1 C9 C10 123.81(13) . . ? C3 C9 C10 119.70(13) . . ? C11 C10 C9 120.07(13) . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? O2 C11 C12 122.99(13) . . ? O2 C11 C10 115.53(13) . . ? C12 C11 C10 121.48(13) . . ? C4 C12 C11 116.19(14) . . ? C4 C12 H12 121.9 . . ? C11 C12 H12 121.9 . . ? O1 C13 H13A 109.5 . . ? O1 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O1 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O2 C14 H14A 109.5 . . ? O2 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? O2 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C16 C15 C7 120.80(15) . . ? C16 C15 H15 119.6 . . ? C7 C15 H15 119.6 . . ? C17 C16 C15 120.24(15) . . ? C17 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? C16 C17 C18 119.49(15) . . ? C16 C17 H17 120.3 . . ? C18 C17 H17 120.3 . . ? C17 C18 C19 120.26(15) . . ? C17 C18 H18 119.9 . . ? C19 C18 H18 119.9 . . ? C18 C19 C7 120.71(14) . . ? C18 C19 H19 119.6 . . ? C7 C19 H19 119.6 . . ? C21 C20 C8 120.82(14) . . ? C21 C20 H20 119.6 . . ? C8 C20 H20 119.6 . . ? C20 C21 C22 120.14(14) . . ? C20 C21 H21 119.9 . . ? C22 C21 H21 119.9 . . ? C21 C22 C23 119.68(14) . . ? C21 C22 H22 120.2 . . ? C23 C22 H22 120.2 . . ? C22 C23 C24 120.27(14) . . ? C22 C23 H23 119.9 . . ? C24 C23 H23 119.9 . . ? C8 C24 C23 120.27(14) . . ? C8 C24 H24 119.9 . . ? C23 C24 H24 119.9 . . ? C39 O4 C43 117.37(12) . . ? C41 O5 C44 117.98(12) . . ? C31 N2 C34 111.62(12) . . ? C31 N2 H2 122.7(12) . . ? C34 N2 H2 125.7(12) . . ? O6 C31 N2 125.91(13) . . ? O6 C31 C32 125.37(13) . . ? N2 C31 C32 108.72(12) . . ? C33 C32 C37 111.38(11) . . ? C33 C32 C38 113.84(12) . . ? C37 C32 C38 115.64(12) . . ? C33 C32 C31 100.57(11) . . ? C37 C32 C31 107.56(11) . . ? C38 C32 C31 106.38(11) . . ? C39 C33 C34 118.83(13) . . ? C39 C33 C32 130.95(13) . . ? C34 C33 C32 110.21(12) . . ? C42 C34 C33 123.41(13) . . ? C42 C34 N2 127.73(13) . . ? C33 C34 N2 108.86(12) . . ? C49 C37 C45 118.19(14) . . ? C49 C37 C32 123.52(13) . . ? C45 C37 C32 118.29(13) . . ? C54 C38 C50 118.54(13) . . ? C54 C38 C32 121.09(13) . . ? C50 C38 C32 120.27(13) . . ? O4 C39 C33 116.01(12) . . ? O4 C39 C40 124.26(13) . . ? C33 C39 C40 119.72(13) . . ? C41 C40 C39 119.56(13) . . ? C41 C40 H40 120.2 . . ? C39 C40 H40 120.2 . . ? O5 C41 C40 123.49(13) . . ? O5 C41 C42 114.81(13) . . ? C40 C41 C42 121.69(13) . . ? C34 C42 C41 116.74(13) . . ? C34 C42 H42 121.6 . . ? C41 C42 H42 121.6 . . ? O4 C43 H43A 109.5 . . ? O4 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? O4 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? O5 C44 H44A 109.5 . . ? O5 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? O5 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? C46 C45 C37 120.98(15) . . ? C46 C45 H45 119.5 . . ? C37 C45 H45 119.5 . . ? C47 C46 C45 120.36(15) . . ? C47 C46 H46 119.8 . . ? C45 C46 H46 119.8 . . ? C46 C47 C48 119.26(15) . . ? C46 C47 H47 120.4 . . ? C48 C47 H47 120.4 . . ? C47 C48 C49 120.52(15) . . ? C47 C48 H48 119.7 . . ? C49 C48 H48 119.7 . . ? C37 C49 C48 120.64(15) . . ? C37 C49 H49 119.7 . . ? C48 C49 H49 119.7 . . ? C51 C50 C38 120.23(14) . . ? C51 C50 H50 119.9 . . ? C38 C50 H50 119.9 . . ? C52 C51 C50 120.81(15) . . ? C52 C51 H51 119.6 . . ? C50 C51 H51 119.6 . . ? C53 C52 C51 119.06(14) . . ? C53 C52 H52 120.5 . . ? C51 C52 H52 120.5 . . ? C52 C53 C54 120.68(15) . . ? C52 C53 H53 119.7 . . ? C54 C53 H53 119.7 . . ? C53 C54 C38 120.65(14) . . ? C53 C54 H54 119.7 . . ? C38 C54 H54 119.7 . . ? 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 C4 N1 C1 O3 176.59(14) . . . . ? C4 N1 C1 C2 -2.19(16) . . . . ? O3 C1 C2 C3 -178.13(14) . . . . ? N1 C1 C2 C3 0.65(14) . . . . ? O3 C1 C2 C8 59.56(18) . . . . ? N1 C1 C2 C8 -121.66(13) . . . . ? O3 C1 C2 C7 -60.74(18) . . . . ? N1 C1 C2 C7 118.04(13) . . . . ? C8 C2 C3 C4 116.53(14) . . . . ? C7 C2 C3 C4 -112.62(13) . . . . ? C1 C2 C3 C4 1.11(15) . . . . ? C8 C2 C3 C9 -66.3(2) . . . . ? C7 C2 C3 C9 64.5(2) . . . . ? C1 C2 C3 C9 178.25(15) . . . . ? C9 C3 C4 C12 0.5(2) . . . . ? C2 C3 C4 C12 178.15(13) . . . . ? C9 C3 C4 N1 179.86(12) . . . . ? C2 C3 C4 N1 -2.48(16) . . . . ? C1 N1 C4 C12 -177.62(14) . . . . ? C1 N1 C4 C3 3.00(17) . . . . ? C3 C2 C7 C19 -98.58(16) . . . . ? C8 C2 C7 C19 34.51(18) . . . . ? C1 C2 C7 C19 151.54(13) . . . . ? C3 C2 C7 C15 81.98(17) . . . . ? C8 C2 C7 C15 -144.93(14) . . . . ? C1 C2 C7 C15 -27.90(18) . . . . ? C3 C2 C8 C24 -0.67(19) . . . . ? C7 C2 C8 C24 -131.53(14) . . . . ? C1 C2 C8 C24 111.35(15) . . . . ? C3 C2 C8 C20 -178.50(12) . . . . ? C7 C2 C8 C20 50.64(16) . . . . ? C1 C2 C8 C20 -66.48(15) . . . . ? C13 O1 C9 C3 -176.66(13) . . . . ? C13 O1 C9 C10 3.6(2) . . . . ? C4 C3 C9 O1 -179.59(13) . . . . ? C2 C3 C9 O1 3.5(2) . . . . ? C4 C3 C9 C10 0.1(2) . . . . ? C2 C3 C9 C10 -176.81(14) . . . . ? O1 C9 C10 C11 179.51(14) . . . . ? C3 C9 C10 C11 -0.2(2) . . . . ? C14 O2 C11 C12 6.1(2) . . . . ? C14 O2 C11 C10 -173.58(14) . . . . ? C9 C10 C11 O2 179.35(13) . . . . ? C9 C10 C11 C12 -0.4(2) . . . . ? C3 C4 C12 C11 -1.0(2) . . . . ? N1 C4 C12 C11 179.71(14) . . . . ? O2 C11 C12 C4 -178.77(14) . . . . ? C10 C11 C12 C4 0.9(2) . . . . ? C19 C7 C15 C16 -1.9(2) . . . . ? C2 C7 C15 C16 177.51(14) . . . . ? C7 C15 C16 C17 0.6(3) . . . . ? C15 C16 C17 C18 1.1(3) . . . . ? C16 C17 C18 C19 -1.3(3) . . . . ? C17 C18 C19 C7 -0.1(2) . . . . ? C15 C7 C19 C18 1.7(2) . . . . ? C2 C7 C19 C18 -177.74(14) . . . . ? C24 C8 C20 C21 0.8(2) . . . . ? C2 C8 C20 C21 178.67(13) . . . . ? C8 C20 C21 C22 -0.3(2) . . . . ? C20 C21 C22 C23 -0.7(2) . . . . ? C21 C22 C23 C24 1.1(2) . . . . ? C20 C8 C24 C23 -0.3(2) . . . . ? C2 C8 C24 C23 -178.17(14) . . . . ? C22 C23 C24 C8 -0.6(2) . . . . ? C34 N2 C31 O6 178.69(13) . . . . ? C34 N2 C31 C32 -0.87(16) . . . . ? O6 C31 C32 C33 -178.15(14) . . . . ? N2 C31 C32 C33 1.42(14) . . . . ? O6 C31 C32 C37 -61.53(17) . . . . ? N2 C31 C32 C37 118.03(12) . . . . ? O6 C31 C32 C38 62.94(17) . . . . ? N2 C31 C32 C38 -117.49(12) . . . . ? C37 C32 C33 C39 63.86(19) . . . . ? C38 C32 C33 C39 -69.06(19) . . . . ? C31 C32 C33 C39 177.61(15) . . . . ? C37 C32 C33 C34 -115.26(13) . . . . ? C38 C32 C33 C34 111.82(13) . . . . ? C31 C32 C33 C34 -1.51(14) . . . . ? C39 C33 C34 C42 1.9(2) . . . . ? C32 C33 C34 C42 -178.91(13) . . . . ? C39 C33 C34 N2 -178.12(12) . . . . ? C32 C33 C34 N2 1.12(16) . . . . ? C31 N2 C34 C42 179.89(14) . . . . ? C31 N2 C34 C33 -0.13(16) . . . . ? C33 C32 C37 C49 -118.66(15) . . . . ? C38 C32 C37 C49 13.36(19) . . . . ? C31 C32 C37 C49 132.04(14) . . . . ? C33 C32 C37 C45 60.93(16) . . . . ? C38 C32 C37 C45 -167.05(13) . . . . ? C31 C32 C37 C45 -48.37(16) . . . . ? C33 C32 C38 C54 -2.36(19) . . . . ? C37 C32 C38 C54 -133.21(14) . . . . ? C31 C32 C38 C54 107.45(15) . . . . ? C33 C32 C38 C50 -178.66(13) . . . . ? C37 C32 C38 C50 50.48(18) . . . . ? C31 C32 C38 C50 -68.85(16) . . . . ? C43 O4 C39 C33 -175.30(13) . . . . ? C43 O4 C39 C40 5.3(2) . . . . ? C34 C33 C39 O4 178.53(12) . . . . ? C32 C33 C39 O4 -0.5(2) . . . . ? C34 C33 C39 C40 -2.1(2) . . . . ? C32 C33 C39 C40 178.87(14) . . . . ? O4 C39 C40 C41 -179.92(13) . . . . ? C33 C39 C40 C41 0.7(2) . . . . ? C44 O5 C41 C40 3.4(2) . . . . ? C44 O5 C41 C42 -177.35(13) . . . . ? C39 C40 C41 O5 -179.89(13) . . . . ? C39 C40 C41 C42 0.9(2) . . . . ? C33 C34 C42 C41 -0.2(2) . . . . ? N2 C34 C42 C41 179.75(14) . . . . ? O5 C41 C42 C34 179.58(12) . . . . ? C40 C41 C42 C34 -1.2(2) . . . . ? C49 C37 C45 C46 -1.0(2) . . . . ? C32 C37 C45 C46 179.35(14) . . . . ? C37 C45 C46 C47 -0.5(2) . . . . ? C45 C46 C47 C48 0.6(2) . . . . ? C46 C47 C48 C49 0.8(2) . . . . ? C45 C37 C49 C48 2.4(2) . . . . ? C32 C37 C49 C48 -177.97(14) . . . . ? C47 C48 C49 C37 -2.4(2) . . . . ? C54 C38 C50 C51 1.6(2) . . . . ? C32 C38 C50 C51 178.04(14) . . . . ? C38 C50 C51 C52 -1.5(3) . . . . ? C50 C51 C52 C53 0.0(3) . . . . ? C51 C52 C53 C54 1.4(3) . . . . ? C52 C53 C54 C38 -1.2(2) . . . . ? C50 C38 C54 C53 -0.3(2) . . . . ? C32 C38 C54 C53 -176.67(14) . . . . ? 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 O3 0.89(2) 1.92(2) 2.7893(17) 168.3(19) 2_665 N2 H2 O6 0.909(19) 1.96(2) 2.8374(16) 162.4(17) 2_656 _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 34.97 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.502 _refine_diff_density_min -0.336 _refine_diff_density_rms 0.071 _database_code_depnum_ccdc_archive 'CCDC 937918' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_3-P21/c _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'jonjk60, 3-P21/c' _chemical_melting_point ? _chemical_formula_moiety 'C22 H19 N O3' _chemical_formula_sum 'C22 H19 N O3' _chemical_formula_weight 345.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' 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 13.3622(17) _cell_length_b 30.607(4) _cell_length_c 8.5678(11) _cell_angle_alpha 90.00 _cell_angle_beta 92.242(3) _cell_angle_gamma 90.00 _cell_volume 3501.4(8) _cell_formula_units_Z 8 _cell_measurement_temperature 100.0(1) _cell_measurement_reflns_used 4082 _cell_measurement_theta_min 2.47 _cell_measurement_theta_max 35.88 _exptl_crystal_description rod _exptl_crystal_colour colorless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.310 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1456 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9693 _exptl_absorpt_correction_T_max 0.9896 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100.0(1) _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 II CCD Platform' _diffrn_measurement_method 'area detector, \w scans per \f' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 83564 _diffrn_reflns_av_R_equivalents 0.0920 _diffrn_reflns_av_sigmaI/netI 0.0905 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -50 _diffrn_reflns_limit_k_max 51 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.53 _diffrn_reflns_theta_max 36.32 _reflns_number_total 16949 _reflns_number_gt 9386 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2011)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction 'SAINT (Bruker, 2009)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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. Amine hydrogen atoms H1 and H2 were found from the difference Fourier map, and their positional and isotropic displacement parameters were refined independently from those of all other atoms. ; _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^)+(0.0682P)^2^+0.0000P] 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 16949 _refine_ls_number_parameters 481 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1191 _refine_ls_R_factor_gt 0.0584 _refine_ls_wR_factor_ref 0.1503 _refine_ls_wR_factor_gt 0.1282 _refine_ls_goodness_of_fit_ref 0.931 _refine_ls_restrained_S_all 0.931 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.37092(6) 0.58883(3) 0.91917(10) 0.01871(18) Uani 1 1 d . . . O2 O 0.50625(7) 0.45567(3) 0.73405(11) 0.0225(2) Uani 1 1 d . . . O3 O 0.68466(6) 0.67216(3) 0.64383(10) 0.01671(17) Uani 1 1 d . . . N1 N 0.65955(8) 0.59808(3) 0.63981(12) 0.01540(19) Uani 1 1 d . . . H1 H 0.7159(14) 0.5902(6) 0.590(2) 0.040(5) Uiso 1 1 d . . . C1 C 0.63701(8) 0.63957(4) 0.67903(13) 0.0139(2) Uani 1 1 d . . . C2 C 0.54031(8) 0.63923(4) 0.77475(13) 0.0132(2) Uani 1 1 d . . . C3 C 0.51682(8) 0.59064(4) 0.77440(13) 0.0135(2) Uani 1 1 d . . . C4 C 0.58965(9) 0.56830(4) 0.69509(13) 0.0143(2) Uani 1 1 d . . . C7 C 0.45884(9) 0.66605(4) 0.68801(14) 0.0141(2) Uani 1 1 d . . . C8 C 0.57034(9) 0.65780(4) 0.93568(14) 0.0146(2) Uani 1 1 d . . . C9 C 0.44048(9) 0.56613(4) 0.83972(14) 0.0148(2) Uani 1 1 d . . . C10 C 0.43949(9) 0.52094(4) 0.82171(14) 0.0164(2) Uani 1 1 d . . . H10 H 0.3875 0.5042 0.8651 0.020 Uiso 1 1 calc R . . C11 C 0.51434(9) 0.49995(4) 0.74023(14) 0.0169(2) Uani 1 1 d . . . C12 C 0.59155(9) 0.52336(4) 0.67383(14) 0.0168(2) Uani 1 1 d . . . H12 H 0.6423 0.5094 0.6175 0.020 Uiso 1 1 calc R . . C13 C 0.29454(10) 0.56409(4) 0.99196(16) 0.0221(3) Uani 1 1 d . . . H13A H 0.2567 0.5833 1.0596 0.033 Uiso 1 1 calc R . . H13B H 0.3255 0.5406 1.0546 0.033 Uiso 1 1 calc R . . H13C H 0.2491 0.5515 0.9114 0.033 Uiso 1 1 calc R . . C14 C 0.57702(11) 0.43252(4) 0.64513(17) 0.0245(3) Uani 1 1 d . . . H14A H 0.5671 0.4010 0.6580 0.037 Uiso 1 1 calc R . . H14B H 0.6451 0.4404 0.6818 0.037 Uiso 1 1 calc R . . H14C H 0.5676 0.4403 0.5345 0.037 Uiso 1 1 calc R . . C15 C 0.46060(10) 0.67151(4) 0.52733(14) 0.0190(2) Uani 1 1 d . . . H15 H 0.5153 0.6602 0.4724 0.023 Uiso 1 1 calc R . . C16 C 0.38396(10) 0.69327(4) 0.44522(15) 0.0225(3) Uani 1 1 d . . . H16 H 0.3863 0.6966 0.3352 0.027 Uiso 1 1 calc R . . C17 C 0.30397(10) 0.71021(4) 0.52440(16) 0.0217(3) Uani 1 1 d . . . H17 H 0.2505 0.7246 0.4689 0.026 Uiso 1 1 calc R . . C18 C 0.30300(10) 0.70593(4) 0.68509(16) 0.0228(3) Uani 1 1 d . . . H18 H 0.2493 0.7180 0.7402 0.027 Uiso 1 1 calc R . . C19 C 0.37968(9) 0.68415(4) 0.76680(15) 0.0190(2) Uani 1 1 d . . . H19 H 0.3781 0.6816 0.8772 0.023 Uiso 1 1 calc R . . C20 C 0.58992(10) 0.70237(4) 0.95136(15) 0.0195(2) Uani 1 1 d . . . H20 H 0.5796 0.7211 0.8638 0.023 Uiso 1 1 calc R . . C21 C 0.62432(10) 0.71968(4) 1.09334(15) 0.0225(3) Uani 1 1 d . . . H21 H 0.6375 0.7501 1.1026 0.027 Uiso 1 1 calc R . . C22 C 0.63950(10) 0.69241(4) 1.22198(15) 0.0216(3) Uani 1 1 d . . . H22 H 0.6634 0.7041 1.3192 0.026 Uiso 1 1 calc R . . C23 C 0.61963(10) 0.64820(4) 1.20734(15) 0.0194(2) Uani 1 1 d . . . H23 H 0.6298 0.6296 1.2952 0.023 Uiso 1 1 calc R . . C24 C 0.58493(9) 0.63071(4) 1.06541(14) 0.0165(2) Uani 1 1 d . . . H24 H 0.5712 0.6003 1.0569 0.020 Uiso 1 1 calc R . . O4 O 1.11903(7) 0.66010(3) 0.13365(11) 0.02173(19) Uani 1 1 d . . . O5 O 0.97799(8) 0.79718(3) 0.27093(12) 0.0266(2) Uani 1 1 d . . . O6 O 0.83655(7) 0.58232(3) 0.48464(11) 0.01877(18) Uani 1 1 d . . . N2 N 0.85141(8) 0.65642(3) 0.45414(13) 0.01651(19) Uani 1 1 d . . . H2 H 0.8030(13) 0.6640(5) 0.519(2) 0.030(4) Uiso 1 1 d . . . C31 C 0.87752(9) 0.61446(4) 0.42940(14) 0.0153(2) Uani 1 1 d . . . C32 C 0.96738(9) 0.61344(4) 0.31944(14) 0.0143(2) Uani 1 1 d . . . C33 C 0.98166(9) 0.66197(4) 0.29324(14) 0.0150(2) Uani 1 1 d . . . C34 C 0.91160(9) 0.68559(4) 0.37331(14) 0.0156(2) Uani 1 1 d . . . C37 C 1.05506(9) 0.59152(4) 0.40977(14) 0.0155(2) Uani 1 1 d . . . C38 C 0.93722(9) 0.58973(4) 0.16700(14) 0.0154(2) Uani 1 1 d . . . C39 C 1.05089(9) 0.68487(4) 0.20777(15) 0.0171(2) Uani 1 1 d . . . C40 C 1.04675(10) 0.73038(4) 0.20310(15) 0.0196(2) Uani 1 1 d . . . H40 H 1.0936 0.7462 0.1445 0.024 Uiso 1 1 calc R . . C41 C 0.97390(10) 0.75283(4) 0.28430(15) 0.0195(2) Uani 1 1 d . . . C42 C 0.90420(10) 0.73077(4) 0.37177(15) 0.0188(2) Uani 1 1 d . . . H42 H 0.8545 0.7458 0.4271 0.023 Uiso 1 1 calc R . . C43 C 1.18290(11) 0.68165(5) 0.0298(2) 0.0313(3) Uani 1 1 d . . . H43A H 1.2200 0.6599 -0.0287 0.047 Uiso 1 1 calc R . . H43B H 1.2302 0.7002 0.0897 0.047 Uiso 1 1 calc R . . H43C H 1.1426 0.6997 -0.0432 0.047 Uiso 1 1 calc R . . C44 C 0.90590(12) 0.82234(4) 0.35219(18) 0.0280(3) Uani 1 1 d . . . H44A H 0.9168 0.8535 0.3328 0.042 Uiso 1 1 calc R . . H44B H 0.9135 0.8165 0.4645 0.042 Uiso 1 1 calc R . . H44C H 0.8382 0.8142 0.3148 0.042 Uiso 1 1 calc R . . C45 C 1.12648(10) 0.61610(4) 0.49252(16) 0.0228(3) Uani 1 1 d . . . H45 H 1.1219 0.6471 0.4918 0.027 Uiso 1 1 calc R . . C46 C 1.20472(11) 0.59585(5) 0.57653(17) 0.0281(3) Uani 1 1 d . . . H46 H 1.2536 0.6130 0.6320 0.034 Uiso 1 1 calc R . . C47 C 1.21117(10) 0.55074(5) 0.57914(16) 0.0237(3) Uani 1 1 d . . . H47 H 1.2648 0.5369 0.6358 0.028 Uiso 1 1 calc R . . C48 C 1.13949(10) 0.52583(4) 0.49916(16) 0.0220(3) Uani 1 1 d . . . H48 H 1.1434 0.4948 0.5020 0.026 Uiso 1 1 calc R . . C49 C 1.06204(9) 0.54617(4) 0.41496(15) 0.0198(2) Uani 1 1 d . . . H49 H 1.0131 0.5289 0.3601 0.024 Uiso 1 1 calc R . . C50 C 1.01002(10) 0.57435(4) 0.06832(15) 0.0207(2) Uani 1 1 d . . . H50 H 1.0788 0.5772 0.0989 0.025 Uiso 1 1 calc R . . C51 C 0.98365(11) 0.55497(5) -0.07360(16) 0.0257(3) Uani 1 1 d . . . H51 H 1.0344 0.5450 -0.1397 0.031 Uiso 1 1 calc R . . C52 C 0.88387(12) 0.55005(5) -0.11951(16) 0.0276(3) Uani 1 1 d . . . H52 H 0.8657 0.5366 -0.2164 0.033 Uiso 1 1 calc R . . C53 C 0.81096(11) 0.56500(5) -0.02272(17) 0.0291(3) Uani 1 1 d . . . H53 H 0.7423 0.5618 -0.0534 0.035 Uiso 1 1 calc R . . C54 C 0.83732(10) 0.58472(5) 0.11946(16) 0.0230(3) Uani 1 1 d . . . H54 H 0.7864 0.5949 0.1847 0.028 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 O1 0.0160(4) 0.0187(4) 0.0218(4) 0.0020(3) 0.0065(3) 0.0004(3) O2 0.0280(5) 0.0122(4) 0.0276(5) -0.0004(3) 0.0036(4) -0.0015(3) O3 0.0178(4) 0.0140(4) 0.0185(4) 0.0008(3) 0.0036(3) -0.0016(3) N1 0.0159(5) 0.0136(4) 0.0170(5) 0.0002(4) 0.0051(4) 0.0004(4) C1 0.0148(5) 0.0143(5) 0.0125(5) 0.0003(4) 0.0002(4) 0.0014(4) C2 0.0142(5) 0.0122(5) 0.0132(5) 0.0002(4) 0.0020(4) 0.0003(4) C3 0.0149(5) 0.0129(5) 0.0128(5) 0.0000(4) 0.0003(4) 0.0004(4) C4 0.0158(5) 0.0141(5) 0.0130(5) 0.0013(4) 0.0002(4) 0.0000(4) C7 0.0159(5) 0.0112(5) 0.0154(5) 0.0008(4) 0.0015(4) 0.0004(4) C8 0.0153(5) 0.0155(5) 0.0131(5) -0.0005(4) 0.0033(4) 0.0010(4) C9 0.0142(5) 0.0167(5) 0.0134(5) 0.0015(4) 0.0003(4) 0.0006(4) C10 0.0166(5) 0.0147(5) 0.0180(6) 0.0030(4) 0.0006(4) -0.0019(4) C11 0.0211(6) 0.0129(5) 0.0164(6) 0.0008(4) -0.0024(4) -0.0002(4) C12 0.0191(5) 0.0146(5) 0.0168(6) -0.0014(4) 0.0021(4) 0.0022(4) C13 0.0184(6) 0.0255(6) 0.0227(6) 0.0053(5) 0.0062(5) -0.0027(5) C14 0.0316(7) 0.0152(6) 0.0268(7) -0.0044(5) 0.0001(5) 0.0019(5) C15 0.0218(6) 0.0196(6) 0.0156(6) -0.0010(4) 0.0019(4) 0.0033(5) C16 0.0288(7) 0.0249(6) 0.0138(6) 0.0014(5) -0.0006(5) 0.0049(5) C17 0.0229(6) 0.0203(6) 0.0216(6) 0.0021(5) -0.0021(5) 0.0063(5) C18 0.0217(6) 0.0244(6) 0.0225(6) 0.0017(5) 0.0043(5) 0.0077(5) C19 0.0195(6) 0.0223(6) 0.0156(6) 0.0021(4) 0.0037(4) 0.0050(5) C20 0.0260(6) 0.0157(5) 0.0168(6) 0.0004(4) 0.0014(5) -0.0014(4) C21 0.0289(7) 0.0180(6) 0.0207(6) -0.0040(5) 0.0019(5) -0.0043(5) C22 0.0240(6) 0.0243(6) 0.0165(6) -0.0041(5) 0.0009(5) 0.0007(5) C23 0.0211(6) 0.0220(6) 0.0152(6) 0.0002(4) 0.0010(4) 0.0042(5) C24 0.0183(5) 0.0159(5) 0.0155(5) 0.0001(4) 0.0018(4) 0.0027(4) O4 0.0210(4) 0.0170(4) 0.0280(5) 0.0035(4) 0.0107(4) -0.0003(3) O5 0.0326(5) 0.0108(4) 0.0362(6) 0.0004(4) -0.0009(4) -0.0009(4) O6 0.0200(4) 0.0146(4) 0.0221(5) 0.0019(3) 0.0066(3) 0.0006(3) N2 0.0180(5) 0.0146(4) 0.0173(5) -0.0002(4) 0.0049(4) 0.0011(4) C31 0.0159(5) 0.0153(5) 0.0147(5) -0.0006(4) 0.0004(4) 0.0013(4) C32 0.0138(5) 0.0133(5) 0.0161(5) 0.0000(4) 0.0025(4) 0.0007(4) C33 0.0158(5) 0.0131(5) 0.0161(5) 0.0005(4) 0.0003(4) -0.0004(4) C34 0.0180(5) 0.0138(5) 0.0150(5) -0.0009(4) 0.0005(4) -0.0011(4) C37 0.0156(5) 0.0157(5) 0.0153(5) 0.0003(4) 0.0022(4) 0.0005(4) C38 0.0179(5) 0.0133(5) 0.0151(5) 0.0006(4) 0.0008(4) 0.0009(4) C39 0.0163(5) 0.0162(5) 0.0189(6) 0.0007(4) 0.0009(4) -0.0010(4) C40 0.0195(6) 0.0165(5) 0.0227(6) 0.0026(4) -0.0009(5) -0.0030(4) C41 0.0240(6) 0.0120(5) 0.0220(6) 0.0001(4) -0.0051(5) -0.0013(4) C42 0.0209(6) 0.0145(5) 0.0207(6) -0.0025(4) -0.0005(5) 0.0021(4) C43 0.0259(7) 0.0263(7) 0.0431(9) 0.0097(6) 0.0181(6) 0.0004(6) C44 0.0353(8) 0.0152(6) 0.0328(8) -0.0029(5) -0.0075(6) 0.0051(5) C45 0.0250(6) 0.0170(6) 0.0257(7) -0.0003(5) -0.0056(5) -0.0002(5) C46 0.0267(7) 0.0270(7) 0.0297(8) -0.0006(6) -0.0110(6) -0.0026(5) C47 0.0209(6) 0.0280(7) 0.0220(7) 0.0028(5) -0.0026(5) 0.0039(5) C48 0.0245(6) 0.0169(6) 0.0246(7) 0.0013(5) 0.0003(5) 0.0041(5) C49 0.0194(6) 0.0163(5) 0.0237(6) -0.0001(4) -0.0017(5) 0.0008(4) C50 0.0203(6) 0.0214(6) 0.0208(6) -0.0027(5) 0.0044(5) 0.0006(5) C51 0.0323(7) 0.0246(7) 0.0206(6) -0.0053(5) 0.0053(5) 0.0039(5) C52 0.0381(8) 0.0260(7) 0.0184(6) -0.0050(5) -0.0045(6) 0.0044(6) C53 0.0253(7) 0.0354(8) 0.0260(7) -0.0060(6) -0.0080(5) 0.0039(6) C54 0.0188(6) 0.0294(7) 0.0207(6) -0.0037(5) -0.0006(5) 0.0050(5) _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 C9 1.3637(14) . ? O1 C13 1.4333(15) . ? O2 C11 1.3606(14) . ? O2 C14 1.4259(16) . ? O3 C1 1.2274(14) . ? N1 C1 1.3506(15) . ? N1 C4 1.4007(15) . ? N1 H1 0.913(19) . ? C1 C2 1.5573(16) . ? C2 C3 1.5201(16) . ? C2 C8 1.5303(16) . ? C2 C7 1.5322(16) . ? C3 C4 1.3885(16) . ? C3 C9 1.4004(16) . ? C4 C12 1.3878(16) . ? C7 C15 1.3879(17) . ? C7 C19 1.3919(16) . ? C8 C24 1.3943(16) . ? C8 C20 1.3946(17) . ? C9 C10 1.3915(16) . ? C10 C11 1.3982(17) . ? C10 H10 0.9500 . ? C11 C12 1.3955(17) . ? C12 H12 0.9500 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C16 1.3895(18) . ? C15 H15 0.9500 . ? C16 C17 1.3886(19) . ? C16 H16 0.9500 . ? C17 C18 1.3835(19) . ? C17 H17 0.9500 . ? C18 C19 1.3886(18) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 C21 1.3884(18) . ? C20 H20 0.9500 . ? C21 C22 1.3911(19) . ? C21 H21 0.9500 . ? C22 C23 1.3838(18) . ? C22 H22 0.9500 . ? C23 C24 1.3914(17) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? O4 C39 1.3610(15) . ? O4 C43 1.4192(16) . ? O5 C41 1.3636(15) . ? O5 C44 1.4347(18) . ? O6 C31 1.2296(14) . ? N2 C31 1.3497(15) . ? N2 C34 1.4025(16) . ? N2 H2 0.898(17) . ? C31 C32 1.5552(16) . ? C32 C33 1.5154(16) . ? C32 C37 1.5332(17) . ? C32 C38 1.5341(17) . ? C33 C34 1.3856(17) . ? C33 C39 1.3916(17) . ? C34 C42 1.3863(16) . ? C37 C45 1.3880(18) . ? C37 C49 1.3917(17) . ? C38 C54 1.3889(18) . ? C38 C50 1.3953(17) . ? C39 C40 1.3943(17) . ? C40 C41 1.3988(18) . ? C40 H40 0.9500 . ? C41 C42 1.3927(18) . ? C42 H42 0.9500 . ? C43 H43A 0.9800 . ? C43 H43B 0.9800 . ? C43 H43C 0.9800 . ? C44 H44A 0.9800 . ? C44 H44B 0.9800 . ? C44 H44C 0.9800 . ? C45 C46 1.3914(19) . ? C45 H45 0.9500 . ? C46 C47 1.384(2) . ? C46 H46 0.9500 . ? C47 C48 1.3846(19) . ? C47 H47 0.9500 . ? C48 C49 1.3859(18) . ? C48 H48 0.9500 . ? C49 H49 0.9500 . ? C50 C51 1.3861(19) . ? C50 H50 0.9500 . ? C51 C52 1.383(2) . ? C51 H51 0.9500 . ? C52 C53 1.382(2) . ? C52 H52 0.9500 . ? C53 C54 1.3924(19) . ? C53 H53 0.9500 . ? C54 H54 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 O1 C13 117.31(10) . . ? C11 O2 C14 117.54(10) . . ? C1 N1 C4 111.69(10) . . ? C1 N1 H1 124.1(11) . . ? C4 N1 H1 124.1(11) . . ? O3 C1 N1 125.46(11) . . ? O3 C1 C2 125.73(10) . . ? N1 C1 C2 108.81(10) . . ? C3 C2 C8 114.33(9) . . ? C3 C2 C7 112.36(9) . . ? C8 C2 C7 113.22(9) . . ? C3 C2 C1 100.43(9) . . ? C8 C2 C1 106.16(9) . . ? C7 C2 C1 109.23(9) . . ? C4 C3 C9 117.86(10) . . ? C4 C3 C2 109.52(10) . . ? C9 C3 C2 132.61(10) . . ? C12 C4 C3 124.68(11) . . ? C12 C4 N1 125.78(11) . . ? C3 C4 N1 109.54(10) . . ? C15 C7 C19 118.41(11) . . ? C15 C7 C2 120.42(10) . . ? C19 C7 C2 121.13(10) . . ? C24 C8 C20 119.02(11) . . ? C24 C8 C2 121.40(10) . . ? C20 C8 C2 119.45(10) . . ? O1 C9 C10 123.92(11) . . ? O1 C9 C3 116.60(10) . . ? C10 C9 C3 119.47(11) . . ? C9 C10 C11 120.54(11) . . ? C9 C10 H10 119.7 . . ? C11 C10 H10 119.7 . . ? O2 C11 C12 123.67(11) . . ? O2 C11 C10 114.83(11) . . ? C12 C11 C10 121.49(11) . . ? C4 C12 C11 115.96(11) . . ? C4 C12 H12 122.0 . . ? C11 C12 H12 122.0 . . ? O1 C13 H13A 109.5 . . ? O1 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O1 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O2 C14 H14A 109.5 . . ? O2 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? O2 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C7 C15 C16 121.28(12) . . ? C7 C15 H15 119.4 . . ? C16 C15 H15 119.4 . . ? C17 C16 C15 119.85(12) . . ? C17 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? C18 C17 C16 119.22(12) . . ? C18 C17 H17 120.4 . . ? C16 C17 H17 120.4 . . ? C17 C18 C19 120.78(12) . . ? C17 C18 H18 119.6 . . ? C19 C18 H18 119.6 . . ? C18 C19 C7 120.42(12) . . ? C18 C19 H19 119.8 . . ? C7 C19 H19 119.8 . . ? C21 C20 C8 120.80(12) . . ? C21 C20 H20 119.6 . . ? C8 C20 H20 119.6 . . ? C20 C21 C22 119.89(12) . . ? C20 C21 H21 120.1 . . ? C22 C21 H21 120.1 . . ? C23 C22 C21 119.56(12) . . ? C23 C22 H22 120.2 . . ? C21 C22 H22 120.2 . . ? C22 C23 C24 120.77(12) . . ? C22 C23 H23 119.6 . . ? C24 C23 H23 119.6 . . ? C23 C24 C8 119.96(11) . . ? C23 C24 H24 120.0 . . ? C8 C24 H24 120.0 . . ? C39 O4 C43 117.59(10) . . ? C41 O5 C44 117.63(11) . . ? C31 N2 C34 111.80(10) . . ? C31 N2 H2 122.7(11) . . ? C34 N2 H2 125.4(11) . . ? O6 C31 N2 125.39(11) . . ? O6 C31 C32 125.66(10) . . ? N2 C31 C32 108.95(10) . . ? C33 C32 C37 113.92(10) . . ? C33 C32 C38 111.59(10) . . ? C37 C32 C38 113.13(9) . . ? C33 C32 C31 100.06(9) . . ? C37 C32 C31 107.21(9) . . ? C38 C32 C31 110.00(9) . . ? C34 C33 C39 118.27(11) . . ? C34 C33 C32 110.28(10) . . ? C39 C33 C32 131.45(11) . . ? C33 C34 C42 124.41(11) . . ? C33 C34 N2 108.90(10) . . ? C42 C34 N2 126.69(11) . . ? C45 C37 C49 118.71(11) . . ? C45 C37 C32 121.15(11) . . ? C49 C37 C32 120.09(11) . . ? C54 C38 C50 118.03(11) . . ? C54 C38 C32 121.29(11) . . ? C50 C38 C32 120.62(11) . . ? O4 C39 C33 115.82(10) . . ? O4 C39 C40 124.72(11) . . ? C33 C39 C40 119.46(11) . . ? C39 C40 C41 120.27(12) . . ? C39 C40 H40 119.9 . . ? C41 C40 H40 119.9 . . ? O5 C41 C42 123.90(12) . . ? O5 C41 C40 114.60(11) . . ? C42 C41 C40 121.50(11) . . ? C34 C42 C41 116.09(11) . . ? C34 C42 H42 122.0 . . ? C41 C42 H42 122.0 . . ? O4 C43 H43A 109.5 . . ? O4 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? O4 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? O5 C44 H44A 109.5 . . ? O5 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? O5 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? C37 C45 C46 120.70(12) . . ? C37 C45 H45 119.6 . . ? C46 C45 H45 119.6 . . ? C47 C46 C45 119.86(13) . . ? C47 C46 H46 120.1 . . ? C45 C46 H46 120.1 . . ? C46 C47 C48 120.01(12) . . ? C46 C47 H47 120.0 . . ? C48 C47 H47 120.0 . . ? C47 C48 C49 119.88(12) . . ? C47 C48 H48 120.1 . . ? C49 C48 H48 120.1 . . ? C48 C49 C37 120.83(12) . . ? C48 C49 H49 119.6 . . ? C37 C49 H49 119.6 . . ? C51 C50 C38 121.10(12) . . ? C51 C50 H50 119.4 . . ? C38 C50 H50 119.4 . . ? C52 C51 C50 120.34(13) . . ? C52 C51 H51 119.8 . . ? C50 C51 H51 119.8 . . ? C53 C52 C51 119.19(13) . . ? C53 C52 H52 120.4 . . ? C51 C52 H52 120.4 . . ? C52 C53 C54 120.55(13) . . ? C52 C53 H53 119.7 . . ? C54 C53 H53 119.7 . . ? C38 C54 C53 120.78(12) . . ? C38 C54 H54 119.6 . . ? C53 C54 H54 119.6 . . ? 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 C4 N1 C1 O3 -178.92(11) . . . . ? C4 N1 C1 C2 0.59(13) . . . . ? O3 C1 C2 C3 178.46(11) . . . . ? N1 C1 C2 C3 -1.05(12) . . . . ? O3 C1 C2 C8 -62.24(14) . . . . ? N1 C1 C2 C8 118.26(10) . . . . ? O3 C1 C2 C7 60.17(15) . . . . ? N1 C1 C2 C7 -119.33(10) . . . . ? C8 C2 C3 C4 -112.02(11) . . . . ? C7 C2 C3 C4 117.14(11) . . . . ? C1 C2 C3 C4 1.17(12) . . . . ? C8 C2 C3 C9 66.20(16) . . . . ? C7 C2 C3 C9 -64.64(16) . . . . ? C1 C2 C3 C9 179.39(12) . . . . ? C9 C3 C4 C12 0.97(18) . . . . ? C2 C3 C4 C12 179.49(11) . . . . ? C9 C3 C4 N1 -179.44(10) . . . . ? C2 C3 C4 N1 -0.92(13) . . . . ? C1 N1 C4 C12 179.78(12) . . . . ? C1 N1 C4 C3 0.20(14) . . . . ? C3 C2 C7 C15 -85.31(13) . . . . ? C8 C2 C7 C15 143.28(11) . . . . ? C1 C2 C7 C15 25.22(15) . . . . ? C3 C2 C7 C19 92.38(13) . . . . ? C8 C2 C7 C19 -39.02(15) . . . . ? C1 C2 C7 C19 -157.08(11) . . . . ? C3 C2 C8 C24 6.65(15) . . . . ? C7 C2 C8 C24 137.07(11) . . . . ? C1 C2 C8 C24 -103.10(12) . . . . ? C3 C2 C8 C20 -177.58(11) . . . . ? C7 C2 C8 C20 -47.16(14) . . . . ? C1 C2 C8 C20 72.68(13) . . . . ? C13 O1 C9 C10 2.04(17) . . . . ? C13 O1 C9 C3 -177.61(11) . . . . ? C4 C3 C9 O1 178.93(10) . . . . ? C2 C3 C9 O1 0.83(19) . . . . ? C4 C3 C9 C10 -0.74(17) . . . . ? C2 C3 C9 C10 -178.84(12) . . . . ? O1 C9 C10 C11 -179.14(11) . . . . ? C3 C9 C10 C11 0.50(18) . . . . ? C14 O2 C11 C12 -4.56(18) . . . . ? C14 O2 C11 C10 176.54(11) . . . . ? C9 C10 C11 O2 178.49(11) . . . . ? C9 C10 C11 C12 -0.43(19) . . . . ? C3 C4 C12 C11 -0.88(18) . . . . ? N1 C4 C12 C11 179.60(11) . . . . ? O2 C11 C12 C4 -178.25(11) . . . . ? C10 C11 C12 C4 0.58(18) . . . . ? C19 C7 C15 C16 -2.02(19) . . . . ? C2 C7 C15 C16 175.74(12) . . . . ? C7 C15 C16 C17 0.4(2) . . . . ? C15 C16 C17 C18 1.4(2) . . . . ? C16 C17 C18 C19 -1.5(2) . . . . ? C17 C18 C19 C7 -0.2(2) . . . . ? C15 C7 C19 C18 1.96(19) . . . . ? C2 C7 C19 C18 -175.78(12) . . . . ? C24 C8 C20 C21 0.58(19) . . . . ? C2 C8 C20 C21 -175.30(12) . . . . ? C8 C20 C21 C22 -0.1(2) . . . . ? C20 C21 C22 C23 -0.3(2) . . . . ? C21 C22 C23 C24 0.18(19) . . . . ? C22 C23 C24 C8 0.35(19) . . . . ? C20 C8 C24 C23 -0.72(18) . . . . ? C2 C8 C24 C23 175.07(11) . . . . ? C34 N2 C31 O6 -179.21(12) . . . . ? C34 N2 C31 C32 0.58(14) . . . . ? O6 C31 C32 C33 179.72(12) . . . . ? N2 C31 C32 C33 -0.07(12) . . . . ? O6 C31 C32 C37 -61.20(15) . . . . ? N2 C31 C32 C37 119.00(11) . . . . ? O6 C31 C32 C38 62.19(15) . . . . ? N2 C31 C32 C38 -117.61(11) . . . . ? C37 C32 C33 C34 -114.50(11) . . . . ? C38 C32 C33 C34 115.88(11) . . . . ? C31 C32 C33 C34 -0.46(13) . . . . ? C37 C32 C33 C39 64.69(17) . . . . ? C38 C32 C33 C39 -64.92(17) . . . . ? C31 C32 C33 C39 178.73(13) . . . . ? C39 C33 C34 C42 1.39(19) . . . . ? C32 C33 C34 C42 -179.30(11) . . . . ? C39 C33 C34 N2 -178.49(11) . . . . ? C32 C33 C34 N2 0.83(14) . . . . ? C31 N2 C34 C33 -0.90(14) . . . . ? C31 N2 C34 C42 179.23(12) . . . . ? C33 C32 C37 C45 15.63(16) . . . . ? C38 C32 C37 C45 144.47(12) . . . . ? C31 C32 C37 C45 -94.09(13) . . . . ? C33 C32 C37 C49 -166.90(11) . . . . ? C38 C32 C37 C49 -38.06(15) . . . . ? C31 C32 C37 C49 83.38(13) . . . . ? C33 C32 C38 C54 -89.92(14) . . . . ? C37 C32 C38 C54 140.05(12) . . . . ? C31 C32 C38 C54 20.19(15) . . . . ? C33 C32 C38 C50 87.03(13) . . . . ? C37 C32 C38 C50 -43.00(15) . . . . ? C31 C32 C38 C50 -162.86(11) . . . . ? C43 O4 C39 C33 172.36(12) . . . . ? C43 O4 C39 C40 -7.69(19) . . . . ? C34 C33 C39 O4 178.90(11) . . . . ? C32 C33 C39 O4 -0.2(2) . . . . ? C34 C33 C39 C40 -1.06(18) . . . . ? C32 C33 C39 C40 179.80(12) . . . . ? O4 C39 C40 C41 -179.65(12) . . . . ? C33 C39 C40 C41 0.31(19) . . . . ? C44 O5 C41 C42 -0.01(18) . . . . ? C44 O5 C41 C40 -179.55(11) . . . . ? C39 C40 C41 O5 179.76(11) . . . . ? C39 C40 C41 C42 0.21(19) . . . . ? C33 C34 C42 C41 -0.87(19) . . . . ? N2 C34 C42 C41 178.98(12) . . . . ? O5 C41 C42 C34 -179.46(12) . . . . ? C40 C41 C42 C34 0.05(18) . . . . ? C49 C37 C45 C46 1.3(2) . . . . ? C32 C37 C45 C46 178.78(13) . . . . ? C37 C45 C46 C47 -0.6(2) . . . . ? C45 C46 C47 C48 -0.4(2) . . . . ? C46 C47 C48 C49 0.8(2) . . . . ? C47 C48 C49 C37 -0.1(2) . . . . ? C45 C37 C49 C48 -0.92(19) . . . . ? C32 C37 C49 C48 -178.45(12) . . . . ? C54 C38 C50 C51 0.52(19) . . . . ? C32 C38 C50 C51 -176.53(12) . . . . ? C38 C50 C51 C52 -0.7(2) . . . . ? C50 C51 C52 C53 0.5(2) . . . . ? C51 C52 C53 C54 -0.1(2) . . . . ? C50 C38 C54 C53 -0.1(2) . . . . ? C32 C38 C54 C53 176.90(12) . . . . ? C52 C53 C54 C38 -0.1(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 H1 O6 0.913(19) 1.893(19) 2.7999(13) 172.1(17) . N2 H2 O3 0.898(17) 1.960(17) 2.8498(14) 170.2(16) . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 36.32 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.646 _refine_diff_density_min -0.281 _refine_diff_density_rms 0.065 _database_code_depnum_ccdc_archive 'CCDC 937919' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common jonjk56 _chemical_melting_point ? _chemical_formula_moiety 'C30 H28 N2 O4' _chemical_formula_sum 'C30 H28 N2 O4' _chemical_formula_weight 480.54 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' 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 10.8867(6) _cell_length_b 11.7612(7) _cell_length_c 19.4486(11) _cell_angle_alpha 90.00 _cell_angle_beta 100.178(1) _cell_angle_gamma 90.00 _cell_volume 2451.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100.0(1) _cell_measurement_reflns_used 4064 _cell_measurement_theta_min 2.57 _cell_measurement_theta_max 24.51 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.302 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1016 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9829 _exptl_absorpt_correction_T_max 0.9914 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100.0(1) _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 II CCD Platform' _diffrn_measurement_method 'area detector, \w scans per \f' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 38229 _diffrn_reflns_av_R_equivalents 0.1120 _diffrn_reflns_av_sigmaI/netI 0.0714 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 28.28 _reflns_number_total 6096 _reflns_number_gt 3542 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2010)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction 'SAINT (Bruker, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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. Amine hydrogen atoms were found from the difference Fourier map and their positional and isotropic displacement parameters were refined independently from those of all other atoms. ; _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^)+(0.0363P)^2^+0.9061P] 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 6096 _refine_ls_number_parameters 337 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1086 _refine_ls_R_factor_gt 0.0515 _refine_ls_wR_factor_ref 0.1210 _refine_ls_wR_factor_gt 0.0969 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.005 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.11839(12) 0.14478(12) 0.56298(7) 0.0242(3) Uani 1 1 d . . . O2 O -0.31148(13) 0.12717(14) 0.46064(7) 0.0350(4) Uani 1 1 d . . . O3 O 0.35219(14) -0.17916(13) 0.30038(8) 0.0348(4) Uani 1 1 d . . . O4 O 0.10305(13) 0.14004(12) 0.21044(7) 0.0263(3) Uani 1 1 d . . . N1 N 0.01322(15) 0.26812(15) 0.33539(9) 0.0229(4) Uani 1 1 d . . . H1 H -0.0225(19) 0.2477(18) 0.2914(11) 0.026(6) Uiso 1 1 d . . . N2 N 0.27153(15) 0.14167(15) 0.44591(9) 0.0224(4) Uani 1 1 d . . . H2 H 0.272(2) 0.1043(19) 0.4855(12) 0.033(6) Uiso 1 1 d . . . C1 C 0.14933(17) 0.24692(17) 0.34958(9) 0.0201(4) Uani 1 1 d . . . C2 C 0.18027(17) 0.23551(17) 0.43367(9) 0.0199(4) Uani 1 1 d . . . C3 C 0.05327(17) 0.20293(16) 0.44786(10) 0.0197(4) Uani 1 1 d . . . C4 C -0.03822(18) 0.22110(17) 0.38981(10) 0.0205(4) Uani 1 1 d . . . C5 C 0.25630(17) 0.07433(17) 0.38560(10) 0.0216(4) Uani 1 1 d . . . C6 C 0.18754(17) 0.12981(17) 0.32913(10) 0.0202(4) Uani 1 1 d . . . C7 C 0.22051(18) 0.34102(18) 0.32035(9) 0.0238(4) Uani 1 1 d . . . C8 C 0.22993(17) 0.34285(17) 0.47235(9) 0.0206(4) Uani 1 1 d . . . C9 C 0.02114(18) 0.16053(17) 0.50881(9) 0.0207(4) Uani 1 1 d . . . C10 C -0.10254(18) 0.13644(17) 0.51120(10) 0.0242(4) Uani 1 1 d . . . H10A H -0.1257 0.1076 0.5527 0.029 Uiso 1 1 calc R . . C11 C -0.19250(18) 0.15511(18) 0.45180(11) 0.0253(5) Uani 1 1 d . . . C12 C -0.16397(18) 0.19769(17) 0.39012(10) 0.0237(4) Uani 1 1 d . . . H12A H -0.2265 0.2103 0.3502 0.028 Uiso 1 1 calc R . . C13 C 0.0897(2) 0.09943(19) 0.62675(10) 0.0296(5) Uani 1 1 d . . . H13A H 0.1665 0.0932 0.6614 0.044 Uiso 1 1 calc R . . H13B H 0.0519 0.0240 0.6179 0.044 Uiso 1 1 calc R . . H13C H 0.0310 0.1501 0.6445 0.044 Uiso 1 1 calc R . . C14 C -0.40851(19) 0.1348(2) 0.40146(12) 0.0389(6) Uani 1 1 d . . . H14A H -0.4888 0.1186 0.4156 0.058 Uiso 1 1 calc R . . H14B H -0.3936 0.0793 0.3662 0.058 Uiso 1 1 calc R . . H14C H -0.4101 0.2116 0.3818 0.058 Uiso 1 1 calc R . . C15 C 0.31270(17) -0.03038(18) 0.38006(10) 0.0235(4) Uani 1 1 d . . . H15A H 0.3586 -0.0679 0.4197 0.028 Uiso 1 1 calc R . . C16 C 0.29852(18) -0.07725(18) 0.31374(11) 0.0262(5) Uani 1 1 d . . . C17 C 0.22955(18) -0.02408(18) 0.25521(10) 0.0256(5) Uani 1 1 d . . . H17A H 0.2211 -0.0585 0.2104 0.031 Uiso 1 1 calc R . . C18 C 0.17344(18) 0.08000(18) 0.26338(10) 0.0232(4) Uani 1 1 d . . . C19 C 0.4402(2) -0.2257(2) 0.35647(13) 0.0457(7) Uani 1 1 d . . . H19A H 0.4827 -0.2906 0.3394 0.069 Uiso 1 1 calc R . . H19B H 0.3965 -0.2511 0.3937 0.069 Uiso 1 1 calc R . . H19C H 0.5017 -0.1675 0.3748 0.069 Uiso 1 1 calc R . . C20 C 0.1079(2) 0.10355(19) 0.14075(10) 0.0300(5) Uani 1 1 d . . . H20A H 0.0502 0.1494 0.1075 0.045 Uiso 1 1 calc R . . H20B H 0.0838 0.0233 0.1355 0.045 Uiso 1 1 calc R . . H20C H 0.1930 0.1129 0.1316 0.045 Uiso 1 1 calc R . . C21 C 0.1706(2) 0.44935(19) 0.30812(10) 0.0306(5) Uani 1 1 d . . . H21A H 0.0881 0.4642 0.3154 0.037 Uiso 1 1 calc R . . C22 C 0.2398(3) 0.5358(2) 0.28536(11) 0.0400(6) Uani 1 1 d . . . H22A H 0.2051 0.6098 0.2778 0.048 Uiso 1 1 calc R . . C23 C 0.3583(3) 0.5150(2) 0.27363(11) 0.0427(7) Uani 1 1 d . . . H23A H 0.4054 0.5746 0.2579 0.051 Uiso 1 1 calc R . . C24 C 0.4089(2) 0.4083(2) 0.28460(12) 0.0401(6) Uani 1 1 d . . . H24A H 0.4909 0.3938 0.2763 0.048 Uiso 1 1 calc R . . C25 C 0.34028(19) 0.3215(2) 0.30786(11) 0.0310(5) Uani 1 1 d . . . H25A H 0.3757 0.2477 0.3153 0.037 Uiso 1 1 calc R . . C26 C 0.35266(18) 0.35188(19) 0.50680(10) 0.0262(5) Uani 1 1 d . . . H26A H 0.4082 0.2897 0.5064 0.031 Uiso 1 1 calc R . . C27 C 0.3949(2) 0.4515(2) 0.54198(11) 0.0309(5) Uani 1 1 d . . . H27A H 0.4783 0.4560 0.5665 0.037 Uiso 1 1 calc R . . C28 C 0.3161(2) 0.5436(2) 0.54131(11) 0.0318(5) Uani 1 1 d . . . H28A H 0.3455 0.6117 0.5649 0.038 Uiso 1 1 calc R . . C29 C 0.19406(19) 0.53622(18) 0.50613(10) 0.0269(5) Uani 1 1 d . . . H29A H 0.1400 0.5999 0.5046 0.032 Uiso 1 1 calc R . . C30 C 0.15115(18) 0.43597(18) 0.47320(10) 0.0237(4) Uani 1 1 d . . . H30A H 0.0665 0.4305 0.4508 0.028 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 O1 0.0264(7) 0.0295(8) 0.0168(7) 0.0022(6) 0.0043(6) 0.0009(6) O2 0.0213(7) 0.0555(11) 0.0296(8) -0.0025(8) 0.0079(6) -0.0098(7) O3 0.0409(9) 0.0265(9) 0.0349(9) -0.0059(7) 0.0008(7) 0.0073(7) O4 0.0327(8) 0.0301(8) 0.0159(7) -0.0007(6) 0.0035(6) 0.0025(7) N1 0.0212(9) 0.0310(10) 0.0162(8) 0.0009(7) 0.0025(7) 0.0010(7) N2 0.0230(9) 0.0267(10) 0.0178(8) 0.0024(8) 0.0039(7) 0.0025(7) C1 0.0203(9) 0.0247(11) 0.0159(9) 0.0006(8) 0.0045(8) -0.0001(8) C2 0.0198(9) 0.0252(11) 0.0146(9) 0.0003(8) 0.0029(8) 0.0016(8) C3 0.0200(9) 0.0211(10) 0.0185(9) -0.0007(8) 0.0049(8) -0.0005(8) C4 0.0220(10) 0.0223(11) 0.0176(9) -0.0023(8) 0.0045(8) -0.0010(8) C5 0.0183(9) 0.0266(11) 0.0209(10) -0.0002(9) 0.0062(8) -0.0036(8) C6 0.0168(9) 0.0251(11) 0.0195(9) 0.0010(8) 0.0056(8) -0.0014(8) C7 0.0287(11) 0.0302(12) 0.0125(9) -0.0012(8) 0.0040(8) -0.0062(9) C8 0.0225(10) 0.0257(11) 0.0149(9) 0.0030(8) 0.0073(8) -0.0024(8) C9 0.0240(10) 0.0210(11) 0.0169(9) -0.0028(8) 0.0031(8) 0.0017(8) C10 0.0290(11) 0.0242(11) 0.0215(10) -0.0008(9) 0.0105(9) -0.0037(9) C11 0.0210(10) 0.0289(12) 0.0275(11) -0.0065(9) 0.0082(8) -0.0038(9) C12 0.0228(10) 0.0265(11) 0.0213(10) -0.0025(9) 0.0022(8) -0.0004(9) C13 0.0391(12) 0.0325(13) 0.0188(10) 0.0037(9) 0.0097(9) 0.0012(10) C14 0.0220(11) 0.0585(17) 0.0359(13) -0.0078(12) 0.0045(10) -0.0122(11) C15 0.0208(10) 0.0261(11) 0.0235(10) 0.0038(9) 0.0035(8) -0.0004(8) C16 0.0240(10) 0.0213(11) 0.0335(11) -0.0028(9) 0.0056(9) -0.0018(9) C17 0.0276(11) 0.0282(12) 0.0206(10) -0.0052(9) 0.0032(8) -0.0031(9) C18 0.0221(10) 0.0282(12) 0.0195(10) 0.0010(9) 0.0049(8) -0.0022(9) C19 0.0515(16) 0.0316(14) 0.0487(15) -0.0071(12) -0.0061(13) 0.0155(12) C20 0.0379(12) 0.0331(13) 0.0188(10) -0.0029(9) 0.0040(9) -0.0012(10) C21 0.0424(13) 0.0299(13) 0.0209(10) 0.0011(9) 0.0094(10) -0.0013(10) C22 0.0670(17) 0.0287(13) 0.0262(12) 0.0010(10) 0.0135(12) -0.0097(12) C23 0.0631(17) 0.0446(16) 0.0214(11) 0.0003(11) 0.0099(11) -0.0290(13) C24 0.0352(13) 0.0563(18) 0.0299(12) 0.0017(12) 0.0090(10) -0.0187(12) C25 0.0287(11) 0.0372(13) 0.0275(11) 0.0009(10) 0.0059(9) -0.0062(10) C26 0.0218(10) 0.0301(12) 0.0265(10) 0.0003(9) 0.0040(8) -0.0019(9) C27 0.0259(11) 0.0366(13) 0.0294(11) -0.0039(10) 0.0032(9) -0.0077(10) C28 0.0359(12) 0.0312(13) 0.0288(11) -0.0041(10) 0.0069(10) -0.0077(10) C29 0.0313(11) 0.0261(12) 0.0242(10) 0.0010(9) 0.0079(9) 0.0002(9) C30 0.0240(10) 0.0301(12) 0.0175(9) -0.0005(9) 0.0046(8) -0.0010(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 O1 C9 1.368(2) . ? O1 C13 1.434(2) . ? O2 C11 1.376(2) . ? O2 C14 1.421(2) . ? O3 C16 1.378(2) . ? O3 C19 1.428(3) . ? O4 C18 1.367(2) . ? O4 C20 1.431(2) . ? N1 C4 1.396(2) . ? N1 C1 1.480(2) . ? N1 H1 0.91(2) . ? N2 C5 1.401(2) . ? N2 C2 1.476(2) . ? N2 H2 0.89(2) . ? C1 C6 1.512(3) . ? C1 C7 1.518(3) . ? C1 C2 1.616(2) . ? C2 C3 1.506(3) . ? C2 C8 1.519(3) . ? C3 C4 1.384(3) . ? C3 C9 1.387(3) . ? C4 C12 1.397(3) . ? C5 C6 1.379(3) . ? C5 C15 1.389(3) . ? C6 C18 1.390(3) . ? C7 C25 1.387(3) . ? C7 C21 1.389(3) . ? C8 C26 1.389(3) . ? C8 C30 1.393(3) . ? C9 C10 1.385(3) . ? C10 C11 1.394(3) . ? C10 H10A 0.9500 . ? C11 C12 1.385(3) . ? C12 H12A 0.9500 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C16 1.386(3) . ? C15 H15A 0.9500 . ? C16 C17 1.396(3) . ? C17 C18 1.390(3) . ? C17 H17A 0.9500 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 C22 1.384(3) . ? C21 H21A 0.9500 . ? C22 C23 1.371(4) . ? C22 H22A 0.9500 . ? C23 C24 1.373(4) . ? C23 H23A 0.9500 . ? C24 C25 1.387(3) . ? C24 H24A 0.9500 . ? C25 H25A 0.9500 . ? C26 C27 1.393(3) . ? C26 H26A 0.9500 . ? C27 C28 1.381(3) . ? C27 H27A 0.9500 . ? C28 C29 1.386(3) . ? C28 H28A 0.9500 . ? C29 C30 1.383(3) . ? C29 H29A 0.9500 . ? C30 H30A 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 O1 C13 117.33(15) . . ? C11 O2 C14 117.72(16) . . ? C16 O3 C19 116.05(17) . . ? C18 O4 C20 116.67(16) . . ? C4 N1 C1 108.33(15) . . ? C4 N1 H1 116.6(13) . . ? C1 N1 H1 112.3(13) . . ? C5 N2 C2 108.13(15) . . ? C5 N2 H2 115.4(15) . . ? C2 N2 H2 114.1(15) . . ? N1 C1 C6 114.67(16) . . ? N1 C1 C7 111.59(16) . . ? C6 C1 C7 112.54(16) . . ? N1 C1 C2 103.03(14) . . ? C6 C1 C2 99.94(15) . . ? C7 C1 C2 114.24(15) . . ? N2 C2 C3 113.19(16) . . ? N2 C2 C8 111.78(15) . . ? C3 C2 C8 112.24(16) . . ? N2 C2 C1 103.84(15) . . ? C3 C2 C1 99.93(14) . . ? C8 C2 C1 115.11(16) . . ? C4 C3 C9 119.93(17) . . ? C4 C3 C2 111.28(17) . . ? C9 C3 C2 128.78(17) . . ? C3 C4 N1 110.63(17) . . ? C3 C4 C12 122.04(18) . . ? N1 C4 C12 127.29(17) . . ? C6 C5 C15 122.88(19) . . ? C6 C5 N2 111.51(18) . . ? C15 C5 N2 125.31(18) . . ? C5 C6 C18 119.30(18) . . ? C5 C6 C1 110.93(17) . . ? C18 C6 C1 129.42(18) . . ? C25 C7 C21 118.3(2) . . ? C25 C7 C1 120.17(19) . . ? C21 C7 C1 121.50(18) . . ? C26 C8 C30 118.43(19) . . ? C26 C8 C2 122.02(18) . . ? C30 C8 C2 119.55(17) . . ? O1 C9 C10 124.83(17) . . ? O1 C9 C3 115.42(17) . . ? C10 C9 C3 119.74(17) . . ? C9 C10 C11 119.01(18) . . ? C9 C10 H10A 120.5 . . ? C11 C10 H10A 120.5 . . ? O2 C11 C12 123.69(18) . . ? O2 C11 C10 113.44(18) . . ? C12 C11 C10 122.87(18) . . ? C11 C12 C4 116.41(18) . . ? C11 C12 H12A 121.8 . . ? C4 C12 H12A 121.8 . . ? O1 C13 H13A 109.5 . . ? O1 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O1 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O2 C14 H14A 109.5 . . ? O2 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? O2 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C16 C15 C5 116.55(19) . . ? C16 C15 H15A 121.7 . . ? C5 C15 H15A 121.7 . . ? O3 C16 C15 122.69(19) . . ? O3 C16 C17 114.89(18) . . ? C15 C16 C17 122.41(19) . . ? C18 C17 C16 119.04(19) . . ? C18 C17 H17A 120.5 . . ? C16 C17 H17A 120.5 . . ? O4 C18 C17 124.63(18) . . ? O4 C18 C6 115.56(18) . . ? C17 C18 C6 119.81(18) . . ? O3 C19 H19A 109.5 . . ? O3 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? O3 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O4 C20 H20A 109.5 . . ? O4 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O4 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C22 C21 C7 120.6(2) . . ? C22 C21 H21A 119.7 . . ? C7 C21 H21A 119.7 . . ? C23 C22 C21 120.3(2) . . ? C23 C22 H22A 119.9 . . ? C21 C22 H22A 119.9 . . ? C22 C23 C24 120.1(2) . . ? C22 C23 H23A 120.0 . . ? C24 C23 H23A 120.0 . . ? C23 C24 C25 119.9(2) . . ? C23 C24 H24A 120.0 . . ? C25 C24 H24A 120.0 . . ? C7 C25 C24 120.8(2) . . ? C7 C25 H25A 119.6 . . ? C24 C25 H25A 119.6 . . ? C8 C26 C27 120.5(2) . . ? C8 C26 H26A 119.8 . . ? C27 C26 H26A 119.8 . . ? C28 C27 C26 120.3(2) . . ? C28 C27 H27A 119.8 . . ? C26 C27 H27A 119.8 . . ? C27 C28 C29 119.7(2) . . ? C27 C28 H28A 120.1 . . ? C29 C28 H28A 120.1 . . ? C30 C29 C28 119.9(2) . . ? C30 C29 H29A 120.1 . . ? C28 C29 H29A 120.1 . . ? C29 C30 C8 121.16(19) . . ? C29 C30 H30A 119.4 . . ? C8 C30 H30A 119.4 . . ? 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 C4 N1 C1 C6 81.54(19) . . . . ? C4 N1 C1 C7 -149.01(16) . . . . ? C4 N1 C1 C2 -26.0(2) . . . . ? C5 N2 C2 C3 84.11(19) . . . . ? C5 N2 C2 C8 -147.97(16) . . . . ? C5 N2 C2 C1 -23.28(19) . . . . ? N1 C1 C2 N2 140.09(15) . . . . ? C6 C1 C2 N2 21.69(17) . . . . ? C7 C1 C2 N2 -98.69(18) . . . . ? N1 C1 C2 C3 23.03(18) . . . . ? C6 C1 C2 C3 -95.37(16) . . . . ? C7 C1 C2 C3 144.26(17) . . . . ? N1 C1 C2 C8 -97.40(18) . . . . ? C6 C1 C2 C8 144.20(16) . . . . ? C7 C1 C2 C8 23.8(2) . . . . ? N2 C2 C3 C4 -123.37(18) . . . . ? C8 C2 C3 C4 108.95(19) . . . . ? C1 C2 C3 C4 -13.5(2) . . . . ? N2 C2 C3 C9 57.1(3) . . . . ? C8 C2 C3 C9 -70.6(3) . . . . ? C1 C2 C3 C9 166.9(2) . . . . ? C9 C3 C4 N1 177.58(18) . . . . ? C2 C3 C4 N1 -2.0(2) . . . . ? C9 C3 C4 C12 -0.2(3) . . . . ? C2 C3 C4 C12 -179.75(18) . . . . ? C1 N1 C4 C3 18.7(2) . . . . ? C1 N1 C4 C12 -163.7(2) . . . . ? C2 N2 C5 C6 15.6(2) . . . . ? C2 N2 C5 C15 -170.55(18) . . . . ? C15 C5 C6 C18 -0.2(3) . . . . ? N2 C5 C6 C18 173.83(17) . . . . ? C15 C5 C6 C1 -174.01(17) . . . . ? N2 C5 C6 C1 0.0(2) . . . . ? N1 C1 C6 C5 -123.13(18) . . . . ? C7 C1 C6 C5 107.89(18) . . . . ? C2 C1 C6 C5 -13.71(19) . . . . ? N1 C1 C6 C18 63.8(3) . . . . ? C7 C1 C6 C18 -65.2(3) . . . . ? C2 C1 C6 C18 173.24(19) . . . . ? N1 C1 C7 C25 -159.25(17) . . . . ? C6 C1 C7 C25 -28.7(2) . . . . ? C2 C1 C7 C25 84.4(2) . . . . ? N1 C1 C7 C21 23.4(2) . . . . ? C6 C1 C7 C21 153.97(18) . . . . ? C2 C1 C7 C21 -93.0(2) . . . . ? N2 C2 C8 C26 7.8(2) . . . . ? C3 C2 C8 C26 136.18(18) . . . . ? C1 C2 C8 C26 -110.4(2) . . . . ? N2 C2 C8 C30 -172.77(17) . . . . ? C3 C2 C8 C30 -44.3(2) . . . . ? C1 C2 C8 C30 69.1(2) . . . . ? C13 O1 C9 C10 0.3(3) . . . . ? C13 O1 C9 C3 -179.09(17) . . . . ? C4 C3 C9 O1 179.52(17) . . . . ? C2 C3 C9 O1 -1.0(3) . . . . ? C4 C3 C9 C10 0.1(3) . . . . ? C2 C3 C9 C10 179.56(19) . . . . ? O1 C9 C10 C11 -179.16(19) . . . . ? C3 C9 C10 C11 0.2(3) . . . . ? C14 O2 C11 C12 4.8(3) . . . . ? C14 O2 C11 C10 -175.20(19) . . . . ? C9 C10 C11 O2 179.55(18) . . . . ? C9 C10 C11 C12 -0.5(3) . . . . ? O2 C11 C12 C4 -179.66(19) . . . . ? C10 C11 C12 C4 0.3(3) . . . . ? C3 C4 C12 C11 0.0(3) . . . . ? N1 C4 C12 C11 -177.40(19) . . . . ? C6 C5 C15 C16 1.0(3) . . . . ? N2 C5 C15 C16 -172.13(18) . . . . ? C19 O3 C16 C15 -9.8(3) . . . . ? C19 O3 C16 C17 169.7(2) . . . . ? C5 C15 C16 O3 178.27(18) . . . . ? C5 C15 C16 C17 -1.1(3) . . . . ? O3 C16 C17 C18 -179.06(18) . . . . ? C15 C16 C17 C18 0.4(3) . . . . ? C20 O4 C18 C17 -12.4(3) . . . . ? C20 O4 C18 C6 167.49(17) . . . . ? C16 C17 C18 O4 -179.54(18) . . . . ? C16 C17 C18 C6 0.5(3) . . . . ? C5 C6 C18 O4 179.43(17) . . . . ? C1 C6 C18 O4 -8.0(3) . . . . ? C5 C6 C18 C17 -0.6(3) . . . . ? C1 C6 C18 C17 171.91(19) . . . . ? C25 C7 C21 C22 -1.2(3) . . . . ? C1 C7 C21 C22 176.15(19) . . . . ? C7 C21 C22 C23 0.9(3) . . . . ? C21 C22 C23 C24 -0.2(3) . . . . ? C22 C23 C24 C25 -0.3(3) . . . . ? C21 C7 C25 C24 0.8(3) . . . . ? C1 C7 C25 C24 -176.63(19) . . . . ? C23 C24 C25 C7 0.0(3) . . . . ? C30 C8 C26 C27 0.8(3) . . . . ? C2 C8 C26 C27 -179.75(18) . . . . ? C8 C26 C27 C28 -1.8(3) . . . . ? C26 C27 C28 C29 0.8(3) . . . . ? C27 C28 C29 C30 1.4(3) . . . . ? C28 C29 C30 C8 -2.5(3) . . . . ? C26 C8 C30 C29 1.4(3) . . . . ? C2 C8 C30 C29 -178.10(18) . . . . ? 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 O4 0.91(2) 2.59(2) 3.158(2) 121.3(16) . N2 H2 O1 0.89(2) 2.48(2) 3.051(2) 122.3(18) . N2 H2 O2 0.89(2) 2.92(2) 3.635(2) 138.6(18) 3_556 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.289 _refine_diff_density_min -0.257 _refine_diff_density_rms 0.054 _database_code_depnum_ccdc_archive 'CCDC 937920' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_5 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common jonjk70 _chemical_melting_point ? _chemical_formula_moiety 'C8 H12 N O2, C7 H7 O3 S' _chemical_formula_sum 'C15 H19 N O5 S' _chemical_formula_weight 325.37 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.031(4) _cell_length_b 5.3646(17) _cell_length_c 22.323(7) _cell_angle_alpha 90.00 _cell_angle_beta 99.179(6) _cell_angle_gamma 90.00 _cell_volume 1540.6(8) _cell_formula_units_Z 4 _cell_measurement_temperature 100.0(5) _cell_measurement_reflns_used 2539 _cell_measurement_theta_min 2.97 _cell_measurement_theta_max 24.61 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.403 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.233 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9166 _exptl_absorpt_correction_T_max 0.9861 _exptl_absorpt_process_details 'TWINABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100.0(5) _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 II CCD Platform' _diffrn_measurement_method 'area detector, \w scans per \f' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24078 _diffrn_reflns_av_R_equivalents 0.1286 _diffrn_reflns_av_sigmaI/netI 0.0846 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 25.03 _reflns_number_total 2727 _reflns_number_gt 1902 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2011)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction 'SAINT (Bruker, 2009)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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. The refinement stalled at R1 = 0.139, at which point twin modeling was required. After the non-merohedral twin law, [ 0.571 0 -0.429 / 0 -1 0 / -1.571 0 -0.571 ], a 180 degree rotation about reciprocal lattice [ -1 0 1 ], was determined, the data were re-integrated, and a new absorption correction was applied. There were 2074 unique reflections solely in the first component, 1960 unique reflections solely in the second component, and 1390 unique overlapping reflections. The mass ratio of the two components refined to 60:40. Ammonium hydrogen atoms were found from the difference Fourier map, and their positional and isotropic displacement parameters were refined indepedently from those of the nitrogen atom. ; _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^)+(0.0401P)^2^+0.7456P] 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 2727 _refine_ls_number_parameters 215 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0945 _refine_ls_R_factor_gt 0.0528 _refine_ls_wR_factor_ref 0.1117 _refine_ls_wR_factor_gt 0.0970 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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 0.68768(19) 1.4063(5) 0.66666(12) 0.0256(7) Uani 1 1 d . . . O2 O 0.55104(19) 0.7315(5) 0.54083(12) 0.0284(7) Uani 1 1 d . . . N1 N 0.9056(2) 0.9453(7) 0.54713(17) 0.0187(8) Uani 1 1 d . . . H1N H 0.903(3) 0.886(7) 0.504(2) 0.028(11) Uiso 1 1 d . . . H2N H 0.944(4) 0.817(9) 0.572(2) 0.053(15) Uiso 1 1 d . . . H3N H 0.949(3) 1.074(8) 0.5569(18) 0.026(12) Uiso 1 1 d . . . C1 C 0.8057(3) 0.9968(7) 0.56645(16) 0.0194(8) Uani 1 1 d . . . C2 C 0.7996(3) 1.1911(7) 0.60660(16) 0.0180(9) Uani 1 1 d . . . H2A H 0.8575 1.2956 0.6201 0.022 Uiso 1 1 calc R . . C3 C 0.7048(3) 1.2257(7) 0.62620(17) 0.0209(9) Uani 1 1 d . . . C4 C 0.6199(3) 1.0758(7) 0.60518(19) 0.0232(9) Uani 1 1 d . . . H4A H 0.5553 1.1044 0.6186 0.028 Uiso 1 1 calc R . . C5 C 0.6291(3) 0.8867(7) 0.56517(17) 0.0210(9) Uani 1 1 d . . . C6 C 0.7238(3) 0.8428(7) 0.54558(17) 0.0193(9) Uani 1 1 d . . . H6A H 0.7314 0.7099 0.5185 0.023 Uiso 1 1 calc R . . C7 C 0.7739(3) 1.5587(8) 0.69178(18) 0.0269(10) Uani 1 1 d . . . H7A H 0.7521 1.6746 0.7213 0.040 Uiso 1 1 calc R . . H7B H 0.7984 1.6532 0.6592 0.040 Uiso 1 1 calc R . . H7C H 0.8302 1.4528 0.7120 0.040 Uiso 1 1 calc R . . C8 C 0.4544(3) 0.7518(9) 0.56337(19) 0.0314(11) Uani 1 1 d . . . H8A H 0.4043 0.6330 0.5420 0.047 Uiso 1 1 calc R . . H8B H 0.4272 0.9216 0.5566 0.047 Uiso 1 1 calc R . . H8C H 0.4656 0.7148 0.6069 0.047 Uiso 1 1 calc R . . S1 S 0.89542(7) 0.51904(18) 0.41658(4) 0.0181(2) Uani 1 1 d . . . O3 O 0.97830(19) 0.4230(5) 0.38596(12) 0.0237(7) Uani 1 1 d . . . O4 O 0.90856(19) 0.7854(4) 0.42934(11) 0.0216(6) Uani 1 1 d . . . O5 O 0.8806(2) 0.3768(5) 0.46967(12) 0.0241(7) Uani 1 1 d . . . C9 C 0.7802(3) 0.4991(7) 0.36327(16) 0.0167(8) Uani 1 1 d . . . C10 C 0.7067(3) 0.6879(7) 0.35930(17) 0.0195(9) Uani 1 1 d . . . H10A H 0.7178 0.8274 0.3858 0.023 Uiso 1 1 calc R . . C11 C 0.6170(3) 0.6727(8) 0.31653(17) 0.0222(9) Uani 1 1 d . . . H11A H 0.5667 0.8020 0.3141 0.027 Uiso 1 1 calc R . . C12 C 0.5996(3) 0.4698(8) 0.27699(17) 0.0221(9) Uani 1 1 d . . . C13 C 0.6745(3) 0.2833(7) 0.28226(17) 0.0206(9) Uani 1 1 d . . . H13A H 0.6644 0.1444 0.2556 0.025 Uiso 1 1 calc R . . C14 C 0.7634(3) 0.2948(7) 0.32542(17) 0.0198(9) Uani 1 1 d . . . H14A H 0.8126 0.1627 0.3289 0.024 Uiso 1 1 calc R . . C15 C 0.5037(3) 0.4588(9) 0.23019(18) 0.0300(10) Uani 1 1 d . . . H15A H 0.5018 0.6035 0.2033 0.045 Uiso 1 1 calc R . . H15B H 0.4422 0.4601 0.2503 0.045 Uiso 1 1 calc R . . H15C H 0.5044 0.3055 0.2064 0.045 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 O1 0.0280(15) 0.0241(16) 0.0260(16) -0.0076(13) 0.0083(12) 0.0006(12) O2 0.0212(15) 0.0312(17) 0.0325(17) -0.0071(14) 0.0031(12) -0.0088(13) N1 0.0163(17) 0.0195(19) 0.020(2) -0.0025(17) 0.0037(14) -0.0008(15) C1 0.0195(19) 0.019(2) 0.020(2) 0.006(2) 0.0036(15) 0.0042(18) C2 0.022(2) 0.016(2) 0.015(2) 0.0026(17) 0.0012(16) -0.0022(16) C3 0.030(2) 0.019(2) 0.015(2) 0.0011(18) 0.0068(16) 0.0035(18) C4 0.017(2) 0.030(2) 0.024(2) 0.005(2) 0.0067(16) 0.0009(18) C5 0.021(2) 0.022(2) 0.019(2) 0.0020(19) -0.0001(16) -0.0025(17) C6 0.023(2) 0.019(2) 0.016(2) 0.0013(18) 0.0030(16) 0.0008(17) C7 0.033(2) 0.022(2) 0.024(2) -0.0074(19) 0.0009(18) -0.0002(19) C8 0.023(2) 0.042(3) 0.031(3) -0.001(2) 0.0093(18) -0.007(2) S1 0.0187(5) 0.0175(5) 0.0179(5) 0.0004(5) 0.0019(3) 0.0002(5) O3 0.0189(14) 0.0240(16) 0.0279(17) -0.0022(13) 0.0031(11) 0.0032(12) O4 0.0230(14) 0.0170(14) 0.0233(16) -0.0022(12) -0.0009(12) -0.0052(12) O5 0.0290(15) 0.0253(16) 0.0177(15) 0.0075(13) 0.0028(11) 0.0010(13) C9 0.0199(19) 0.014(2) 0.0163(19) 0.0015(19) 0.0026(15) 0.0017(18) C10 0.021(2) 0.021(2) 0.018(2) -0.0025(18) 0.0070(16) -0.0019(17) C11 0.019(2) 0.024(2) 0.025(2) 0.0080(19) 0.0076(17) 0.0063(17) C12 0.0198(19) 0.027(2) 0.020(2) 0.004(2) 0.0046(15) -0.0080(19) C13 0.028(2) 0.017(2) 0.018(2) -0.0041(17) 0.0056(17) -0.0064(18) C14 0.023(2) 0.018(2) 0.020(2) 0.0023(19) 0.0056(17) 0.0032(17) C15 0.023(2) 0.038(3) 0.026(2) -0.001(2) -0.0031(17) -0.004(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 O1 C3 1.367(4) . ? O1 C7 1.430(4) . ? O2 C5 1.359(4) . ? O2 C8 1.433(4) . ? N1 C1 1.462(5) . ? N1 H1N 1.00(4) . ? N1 H2N 0.96(5) . ? N1 H3N 0.90(4) . ? C1 C6 1.371(5) . ? C1 C2 1.385(5) . ? C2 C3 1.387(5) . ? C2 H2A 0.9500 . ? C3 C4 1.387(5) . ? C4 C5 1.369(6) . ? C4 H4A 0.9500 . ? C5 C6 1.393(5) . ? C6 H6A 0.9500 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? S1 O5 1.448(3) . ? S1 O3 1.461(3) . ? S1 O4 1.462(3) . ? S1 C9 1.764(4) . ? C9 C14 1.380(5) . ? C9 C10 1.387(5) . ? C10 C11 1.389(5) . ? C10 H10A 0.9500 . ? C11 C12 1.397(5) . ? C11 H11A 0.9500 . ? C12 C13 1.389(5) . ? C12 C15 1.497(5) . ? C13 C14 1.386(5) . ? C13 H13A 0.9500 . ? C14 H14A 0.9500 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 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 C3 O1 C7 117.7(3) . . ? C5 O2 C8 117.2(3) . . ? C1 N1 H1N 116(2) . . ? C1 N1 H2N 112(3) . . ? H1N N1 H2N 104(3) . . ? C1 N1 H3N 110(3) . . ? H1N N1 H3N 114(3) . . ? H2N N1 H3N 99(3) . . ? C6 C1 C2 123.4(3) . . ? C6 C1 N1 117.9(3) . . ? C2 C1 N1 118.7(3) . . ? C1 C2 C3 116.8(3) . . ? C1 C2 H2A 121.6 . . ? C3 C2 H2A 121.6 . . ? O1 C3 C4 115.4(3) . . ? O1 C3 C2 123.4(4) . . ? C4 C3 C2 121.2(4) . . ? C5 C4 C3 120.1(4) . . ? C5 C4 H4A 119.9 . . ? C3 C4 H4A 119.9 . . ? O2 C5 C4 125.2(3) . . ? O2 C5 C6 114.5(3) . . ? C4 C5 C6 120.3(4) . . ? C1 C6 C5 118.2(4) . . ? C1 C6 H6A 120.9 . . ? C5 C6 H6A 120.9 . . ? O1 C7 H7A 109.5 . . ? O1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? O1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O2 C8 H8A 109.5 . . ? O2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? O2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O5 S1 O3 113.71(16) . . ? O5 S1 O4 112.49(16) . . ? O3 S1 O4 111.31(16) . . ? O5 S1 C9 108.06(16) . . ? O3 S1 C9 106.02(16) . . ? O4 S1 C9 104.56(16) . . ? C14 C9 C10 120.0(3) . . ? C14 C9 S1 119.7(3) . . ? C10 C9 S1 120.2(3) . . ? C9 C10 C11 119.9(4) . . ? C9 C10 H10A 120.1 . . ? C11 C10 H10A 120.1 . . ? C10 C11 C12 120.9(4) . . ? C10 C11 H11A 119.5 . . ? C12 C11 H11A 119.5 . . ? C13 C12 C11 117.9(3) . . ? C13 C12 C15 121.8(4) . . ? C11 C12 C15 120.3(4) . . ? C14 C13 C12 121.7(4) . . ? C14 C13 H13A 119.2 . . ? C12 C13 H13A 119.2 . . ? C9 C14 C13 119.6(4) . . ? C9 C14 H14A 120.2 . . ? C13 C14 H14A 120.2 . . ? C12 C15 H15A 109.5 . . ? C12 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C12 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 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 0.5(6) . . . . ? N1 C1 C2 C3 -176.8(3) . . . . ? C7 O1 C3 C4 177.3(3) . . . . ? C7 O1 C3 C2 -2.9(5) . . . . ? C1 C2 C3 O1 178.7(3) . . . . ? C1 C2 C3 C4 -1.5(6) . . . . ? O1 C3 C4 C5 -179.0(3) . . . . ? C2 C3 C4 C5 1.2(6) . . . . ? C8 O2 C5 C4 -6.5(6) . . . . ? C8 O2 C5 C6 174.4(3) . . . . ? C3 C4 C5 O2 -178.8(4) . . . . ? C3 C4 C5 C6 0.3(6) . . . . ? C2 C1 C6 C5 1.0(6) . . . . ? N1 C1 C6 C5 178.2(3) . . . . ? O2 C5 C6 C1 177.9(3) . . . . ? C4 C5 C6 C1 -1.4(6) . . . . ? O5 S1 C9 C14 -83.0(3) . . . . ? O3 S1 C9 C14 39.2(3) . . . . ? O4 S1 C9 C14 156.9(3) . . . . ? O5 S1 C9 C10 97.0(3) . . . . ? O3 S1 C9 C10 -140.7(3) . . . . ? O4 S1 C9 C10 -23.0(3) . . . . ? C14 C9 C10 C11 -1.0(5) . . . . ? S1 C9 C10 C11 179.0(3) . . . . ? C9 C10 C11 C12 -0.4(5) . . . . ? C10 C11 C12 C13 0.6(5) . . . . ? C10 C11 C12 C15 -178.6(4) . . . . ? C11 C12 C13 C14 0.4(5) . . . . ? C15 C12 C13 C14 179.6(4) . . . . ? C10 C9 C14 C13 2.0(5) . . . . ? S1 C9 C14 C13 -177.9(3) . . . . ? C12 C13 C14 C9 -1.8(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 H1N O4 1.00(4) 1.78(4) 2.772(4) 176(3) . N1 H2N O3 0.96(5) 1.81(5) 2.775(4) 176(4) 3_766 N1 H3N O4 0.90(4) 1.98(4) 2.796(4) 150(4) 3_776 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.312 _refine_diff_density_min -0.393 _refine_diff_density_rms 0.083 _database_code_depnum_ccdc_archive 'CCDC 937921' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_6b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common jonjk62 _chemical_melting_point ? _chemical_formula_moiety 'C23 H21 N O3' _chemical_formula_sum 'C23 H21 N O3' _chemical_formula_weight 359.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' 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 9.0505(18) _cell_length_b 23.669(5) _cell_length_c 8.6237(18) _cell_angle_alpha 90.00 _cell_angle_beta 97.838(4) _cell_angle_gamma 90.00 _cell_volume 1830.0(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100.0(5) _cell_measurement_reflns_used 3346 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 26.95 _exptl_crystal_description plate _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.304 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9729 _exptl_absorpt_correction_T_max 0.9931 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100.0(5) _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 II CCD Platform' _diffrn_measurement_method 'area detector, \w scans per \f' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21409 _diffrn_reflns_av_R_equivalents 0.0942 _diffrn_reflns_av_sigmaI/netI 0.0743 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4191 _reflns_number_gt 2558 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2011)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction 'SAINT (Bruker, 2009)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0410P)^2^+1.2496P] 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 4191 _refine_ls_number_parameters 247 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1121 _refine_ls_R_factor_gt 0.0619 _refine_ls_wR_factor_ref 0.1470 _refine_ls_wR_factor_gt 0.1275 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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 0.3386(2) 0.15482(7) 0.9184(2) 0.0373(5) Uani 1 1 d . . . O2 O 0.21532(19) -0.08644(7) 0.4586(2) 0.0349(4) Uani 1 1 d . . . O3 O 0.62597(18) -0.00153(7) 0.8013(2) 0.0325(4) Uani 1 1 d . . . N1 N 0.1171(2) 0.04593(8) 0.8394(2) 0.0289(5) Uani 1 1 d . . . C1 C 0.2414(3) 0.13806(10) 0.8164(3) 0.0310(6) Uani 1 1 d . . . C2 C 0.1201(3) 0.09918(10) 0.8626(3) 0.0277(6) Uani 1 1 d . . . C3 C 0.2279(3) 0.01805(10) 0.7658(3) 0.0265(5) Uani 1 1 d . . . C4 C 0.1757(3) -0.01984(10) 0.6468(3) 0.0279(6) Uani 1 1 d . . . H4A H 0.0717 -0.0238 0.6141 0.033 Uiso 1 1 calc R . . C5 C 0.2768(3) -0.05152(10) 0.5771(3) 0.0278(5) Uani 1 1 d . . . C6 C 0.4295(3) -0.04760(10) 0.6255(3) 0.0287(6) Uani 1 1 d . . . H6A H 0.4981 -0.0699 0.5780 0.034 Uiso 1 1 calc R . . C7 C 0.4789(3) -0.00986(10) 0.7459(3) 0.0281(6) Uani 1 1 d . . . C8 C 0.3796(3) 0.02283(10) 0.8156(3) 0.0283(6) Uani 1 1 d . . . H8A H 0.4152 0.0484 0.8972 0.034 Uiso 1 1 calc R . . C9 C 0.3131(3) -0.12268(11) 0.3881(3) 0.0331(6) Uani 1 1 d . . . H9A H 0.2548 -0.1461 0.3084 0.050 Uiso 1 1 calc R . . H9B H 0.3675 -0.1470 0.4684 0.050 Uiso 1 1 calc R . . H9C H 0.3842 -0.0998 0.3391 0.050 Uiso 1 1 calc R . . C10 C 0.7316(3) -0.04021(11) 0.7527(3) 0.0337(6) Uani 1 1 d . . . H10A H 0.8314 -0.0311 0.8060 0.051 Uiso 1 1 calc R . . H10B H 0.7309 -0.0373 0.6393 0.051 Uiso 1 1 calc R . . H10C H 0.7051 -0.0788 0.7795 0.051 Uiso 1 1 calc R . . C11 C 0.2334(3) 0.15490(10) 0.6506(3) 0.0307(6) Uani 1 1 d . . . C12 C 0.1137(3) 0.13913(10) 0.5406(3) 0.0333(6) Uani 1 1 d . . . H12A H 0.0363 0.1164 0.5713 0.040 Uiso 1 1 calc R . . C13 C 0.1070(3) 0.15652(11) 0.3865(3) 0.0364(6) Uani 1 1 d . . . H13A H 0.0243 0.1460 0.3121 0.044 Uiso 1 1 calc R . . C14 C 0.2206(3) 0.18931(11) 0.3400(4) 0.0380(7) Uani 1 1 d . . . H14A H 0.2166 0.2006 0.2338 0.046 Uiso 1 1 calc R . . C15 C 0.3396(3) 0.20538(11) 0.4490(4) 0.0393(7) Uani 1 1 d . . . H15A H 0.4171 0.2280 0.4178 0.047 Uiso 1 1 calc R . . C16 C 0.3462(3) 0.18854(11) 0.6037(4) 0.0368(6) Uani 1 1 d . . . H16A H 0.4279 0.1999 0.6783 0.044 Uiso 1 1 calc R . . C17 C 0.0002(3) 0.12675(10) 0.9376(3) 0.0283(6) Uani 1 1 d . . . C18 C -0.1108(3) 0.09406(10) 0.9915(3) 0.0287(6) Uani 1 1 d . . . H18A H -0.1079 0.0541 0.9828 0.034 Uiso 1 1 calc R . . C19 C -0.2242(3) 0.11934(10) 1.0572(3) 0.0298(6) Uani 1 1 d . . . H19A H -0.2997 0.0965 1.0918 0.036 Uiso 1 1 calc R . . C20 C -0.2303(3) 0.17779(11) 1.0738(3) 0.0300(6) Uani 1 1 d . . . C21 C -0.1212(3) 0.21022(11) 1.0188(3) 0.0353(6) Uani 1 1 d . . . H21A H -0.1247 0.2502 1.0274 0.042 Uiso 1 1 calc R . . C22 C -0.0074(3) 0.18517(10) 0.9517(3) 0.0325(6) Uani 1 1 d . . . H22A H 0.0665 0.2081 0.9147 0.039 Uiso 1 1 calc R . . C23 C -0.3486(3) 0.20421(12) 1.1557(4) 0.0440(7) Uani 1 1 d . . . H23A H -0.4469 0.1914 1.1067 0.066 Uiso 1 1 calc R . . H23B H -0.3426 0.2454 1.1478 0.066 Uiso 1 1 calc R . . H23C H -0.3335 0.1931 1.2662 0.066 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 O1 0.0316(10) 0.0332(10) 0.0453(12) -0.0052(9) -0.0007(9) -0.0049(8) O2 0.0278(10) 0.0394(10) 0.0362(11) -0.0092(8) 0.0001(8) -0.0011(8) O3 0.0240(9) 0.0305(9) 0.0422(11) -0.0056(8) 0.0015(8) 0.0004(7) N1 0.0275(11) 0.0279(11) 0.0308(12) 0.0010(9) 0.0021(9) 0.0007(9) C1 0.0248(13) 0.0236(12) 0.0442(16) -0.0039(11) 0.0028(11) 0.0026(10) C2 0.0242(13) 0.0285(13) 0.0294(14) -0.0007(10) 0.0005(10) -0.0001(10) C3 0.0251(12) 0.0231(12) 0.0324(14) 0.0029(10) 0.0078(11) 0.0015(10) C4 0.0232(12) 0.0283(13) 0.0316(14) 0.0042(11) 0.0019(11) -0.0017(10) C5 0.0296(13) 0.0250(12) 0.0284(14) 0.0033(10) 0.0027(11) -0.0040(10) C6 0.0285(13) 0.0273(12) 0.0308(14) 0.0021(11) 0.0057(11) 0.0006(10) C7 0.0246(13) 0.0238(12) 0.0354(15) 0.0047(11) 0.0020(11) -0.0007(10) C8 0.0300(13) 0.0241(12) 0.0297(14) 0.0006(10) 0.0000(11) -0.0026(10) C9 0.0323(15) 0.0320(14) 0.0345(16) -0.0038(11) 0.0025(12) 0.0033(11) C10 0.0259(13) 0.0349(14) 0.0397(16) -0.0025(12) 0.0020(12) 0.0045(11) C11 0.0272(13) 0.0251(12) 0.0400(15) -0.0021(11) 0.0057(11) 0.0004(10) C12 0.0294(14) 0.0265(13) 0.0440(17) -0.0033(12) 0.0049(12) -0.0022(10) C13 0.0336(15) 0.0316(14) 0.0433(17) -0.0017(12) 0.0032(12) 0.0017(11) C14 0.0388(16) 0.0289(14) 0.0469(18) 0.0016(12) 0.0084(13) 0.0017(12) C15 0.0352(15) 0.0326(14) 0.0515(19) 0.0039(13) 0.0111(14) -0.0035(11) C16 0.0277(14) 0.0330(14) 0.0490(18) -0.0031(13) 0.0030(12) -0.0028(11) C17 0.0264(13) 0.0276(13) 0.0292(14) 0.0007(10) -0.0018(11) 0.0017(10) C18 0.0287(13) 0.0255(12) 0.0308(14) 0.0014(11) -0.0003(11) -0.0002(10) C19 0.0303(14) 0.0314(13) 0.0271(14) 0.0030(11) 0.0018(11) -0.0025(10) C20 0.0305(14) 0.0321(13) 0.0267(14) 0.0002(11) 0.0021(11) 0.0025(11) C21 0.0393(16) 0.0243(13) 0.0423(17) -0.0001(12) 0.0052(13) 0.0013(11) C22 0.0326(14) 0.0286(13) 0.0365(15) 0.0026(11) 0.0059(12) -0.0004(11) C23 0.0386(16) 0.0432(17) 0.0496(19) -0.0008(14) 0.0046(14) 0.0041(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.223(3) . ? O2 C5 1.372(3) . ? O2 C9 1.427(3) . ? O3 C7 1.366(3) . ? O3 C10 1.427(3) . ? N1 C2 1.276(3) . ? N1 C3 1.420(3) . ? C1 C11 1.477(4) . ? C1 C2 1.526(3) . ? C2 C17 1.488(3) . ? C3 C8 1.386(3) . ? C3 C4 1.395(3) . ? C4 C5 1.382(3) . ? C4 H4A 0.9500 . ? C5 C6 1.392(3) . ? C6 C7 1.396(3) . ? C6 H6A 0.9500 . ? C7 C8 1.384(3) . ? C8 H8A 0.9500 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.390(4) . ? C11 C16 1.397(4) . ? C12 C13 1.385(4) . ? C12 H12A 0.9500 . ? C13 C14 1.390(4) . ? C13 H13A 0.9500 . ? C14 C15 1.383(4) . ? C14 H14A 0.9500 . ? C15 C16 1.385(4) . ? C15 H15A 0.9500 . ? C16 H16A 0.9500 . ? C17 C22 1.390(3) . ? C17 C18 1.396(3) . ? C18 C19 1.375(3) . ? C18 H18A 0.9500 . ? C19 C20 1.393(3) . ? C19 H19A 0.9500 . ? C20 C21 1.384(4) . ? C20 C23 1.498(4) . ? C21 C22 1.383(4) . ? C21 H21A 0.9500 . ? C22 H22A 0.9500 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 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 C5 O2 C9 117.89(19) . . ? C7 O3 C10 117.70(19) . . ? C2 N1 C3 121.9(2) . . ? O1 C1 C11 123.0(2) . . ? O1 C1 C2 118.7(2) . . ? C11 C1 C2 118.3(2) . . ? N1 C2 C17 120.0(2) . . ? N1 C2 C1 123.7(2) . . ? C17 C2 C1 116.3(2) . . ? C8 C3 C4 120.1(2) . . ? C8 C3 N1 123.6(2) . . ? C4 C3 N1 116.0(2) . . ? C5 C4 C3 119.4(2) . . ? C5 C4 H4A 120.3 . . ? C3 C4 H4A 120.3 . . ? O2 C5 C4 115.2(2) . . ? O2 C5 C6 123.3(2) . . ? C4 C5 C6 121.5(2) . . ? C5 C6 C7 118.0(2) . . ? C5 C6 H6A 121.0 . . ? C7 C6 H6A 121.0 . . ? O3 C7 C8 115.3(2) . . ? O3 C7 C6 123.4(2) . . ? C8 C7 C6 121.3(2) . . ? C7 C8 C3 119.6(2) . . ? C7 C8 H8A 120.2 . . ? C3 C8 H8A 120.2 . . ? O2 C9 H9A 109.5 . . ? O2 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? O2 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O3 C10 H10A 109.5 . . ? O3 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? O3 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 C16 119.2(3) . . ? C12 C11 C1 121.3(2) . . ? C16 C11 C1 119.5(2) . . ? C13 C12 C11 120.2(3) . . ? C13 C12 H12A 119.9 . . ? C11 C12 H12A 119.9 . . ? C12 C13 C14 120.4(3) . . ? C12 C13 H13A 119.8 . . ? C14 C13 H13A 119.8 . . ? C15 C14 C13 119.7(3) . . ? C15 C14 H14A 120.2 . . ? C13 C14 H14A 120.2 . . ? C14 C15 C16 120.2(3) . . ? C14 C15 H15A 119.9 . . ? C16 C15 H15A 119.9 . . ? C15 C16 C11 120.3(3) . . ? C15 C16 H16A 119.8 . . ? C11 C16 H16A 119.8 . . ? C22 C17 C18 118.4(2) . . ? C22 C17 C2 121.4(2) . . ? C18 C17 C2 120.1(2) . . ? C19 C18 C17 120.5(2) . . ? C19 C18 H18A 119.8 . . ? C17 C18 H18A 119.8 . . ? C18 C19 C20 121.1(2) . . ? C18 C19 H19A 119.4 . . ? C20 C19 H19A 119.4 . . ? C21 C20 C19 118.4(2) . . ? C21 C20 C23 121.3(2) . . ? C19 C20 C23 120.3(2) . . ? C22 C21 C20 120.8(2) . . ? C22 C21 H21A 119.6 . . ? C20 C21 H21A 119.6 . . ? C21 C22 C17 120.7(2) . . ? C21 C22 H22A 119.6 . . ? C17 C22 H22A 119.6 . . ? C20 C23 H23A 109.5 . . ? C20 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C20 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 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 C3 N1 C2 C17 178.9(2) . . . . ? C3 N1 C2 C1 -0.6(4) . . . . ? O1 C1 C2 N1 -103.0(3) . . . . ? C11 C1 C2 N1 78.5(3) . . . . ? O1 C1 C2 C17 77.4(3) . . . . ? C11 C1 C2 C17 -101.0(3) . . . . ? C2 N1 C3 C8 53.5(3) . . . . ? C2 N1 C3 C4 -132.6(2) . . . . ? C8 C3 C4 C5 -1.4(4) . . . . ? N1 C3 C4 C5 -175.5(2) . . . . ? C9 O2 C5 C4 -176.4(2) . . . . ? C9 O2 C5 C6 3.6(3) . . . . ? C3 C4 C5 O2 -178.3(2) . . . . ? C3 C4 C5 C6 1.7(4) . . . . ? O2 C5 C6 C7 179.0(2) . . . . ? C4 C5 C6 C7 -0.9(4) . . . . ? C10 O3 C7 C8 170.0(2) . . . . ? C10 O3 C7 C6 -11.3(3) . . . . ? C5 C6 C7 O3 -178.7(2) . . . . ? C5 C6 C7 C8 0.0(4) . . . . ? O3 C7 C8 C3 179.0(2) . . . . ? C6 C7 C8 C3 0.2(4) . . . . ? C4 C3 C8 C7 0.5(4) . . . . ? N1 C3 C8 C7 174.1(2) . . . . ? O1 C1 C11 C12 -174.0(2) . . . . ? C2 C1 C11 C12 4.3(3) . . . . ? O1 C1 C11 C16 4.3(4) . . . . ? C2 C1 C11 C16 -177.4(2) . . . . ? C16 C11 C12 C13 0.2(4) . . . . ? C1 C11 C12 C13 178.5(2) . . . . ? C11 C12 C13 C14 0.7(4) . . . . ? C12 C13 C14 C15 -1.1(4) . . . . ? C13 C14 C15 C16 0.5(4) . . . . ? C14 C15 C16 C11 0.5(4) . . . . ? C12 C11 C16 C15 -0.8(4) . . . . ? C1 C11 C16 C15 -179.1(2) . . . . ? N1 C2 C17 C22 -174.0(2) . . . . ? C1 C2 C17 C22 5.5(4) . . . . ? N1 C2 C17 C18 4.0(4) . . . . ? C1 C2 C17 C18 -176.5(2) . . . . ? C22 C17 C18 C19 -0.2(4) . . . . ? C2 C17 C18 C19 -178.3(2) . . . . ? C17 C18 C19 C20 -1.0(4) . . . . ? C18 C19 C20 C21 1.6(4) . . . . ? C18 C19 C20 C23 -175.7(2) . . . . ? C19 C20 C21 C22 -1.2(4) . . . . ? C23 C20 C21 C22 176.1(3) . . . . ? C20 C21 C22 C17 0.0(4) . . . . ? C18 C17 C22 C21 0.6(4) . . . . ? C2 C17 C22 C21 178.7(2) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.480 _refine_diff_density_min -0.307 _refine_diff_density_rms 0.050 _database_code_depnum_ccdc_archive 'CCDC 937922' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_7 _vrf_PLAT026_jonjk61 ; PROBLEM: _C Ratio Observed / Unique Reflections too Low .... 45 Perc. RESPONSE: The small crystal diffracted weakly. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common jonjk61 _chemical_melting_point ? _chemical_formula_moiety 'C23 H21 N O3' _chemical_formula_sum 'C23 H21 N O3' _chemical_formula_weight 359.41 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 8.2312(16) _cell_length_b 9.912(2) _cell_length_c 23.000(5) _cell_angle_alpha 81.845(4) _cell_angle_beta 87.012(4) _cell_angle_gamma 89.587(3) _cell_volume 1854.9(6) _cell_formula_units_Z 4 _cell_measurement_temperature 173.0(5) _cell_measurement_reflns_used 1741 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 22.69 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.287 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9782 _exptl_absorpt_correction_T_max 0.9932 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173.0(5) _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 II CCD Platform' _diffrn_measurement_method 'area detector, \w scans per \f' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16814 _diffrn_reflns_av_R_equivalents 0.1103 _diffrn_reflns_av_sigmaI/netI 0.1381 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 25.03 _reflns_number_total 6550 _reflns_number_gt 2958 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2011)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction 'SAINT (Bruker, 2009)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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. The amine hydrogen atoms were found from the difference Fourier map, and their positional and isotropic displacement parameters were refined independently from those of their bonded nitrogen atoms. ; _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^)+(0.0577P)^2^+0.0000P] 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 0.0050(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6550 _refine_ls_number_parameters 502 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1722 _refine_ls_R_factor_gt 0.0663 _refine_ls_wR_factor_ref 0.1646 _refine_ls_wR_factor_gt 0.1259 _refine_ls_goodness_of_fit_ref 0.961 _refine_ls_restrained_S_all 0.961 _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 0.9197(3) 0.9594(3) 0.35395(13) 0.0494(8) Uani 1 1 d . . . O2 O 0.7345(4) 1.0864(3) 0.54235(12) 0.0492(8) Uani 1 1 d . . . O3 O 0.5793(3) 0.4894(2) 0.42449(12) 0.0411(8) Uani 1 1 d . . . N1 N 0.5923(4) 0.6636(3) 0.47895(15) 0.0348(9) Uani 1 1 d . . . H1 H 0.524(4) 0.631(4) 0.5120(16) 0.036(11) Uiso 1 1 d . . . C1 C 0.6268(5) 0.6018(4) 0.43115(18) 0.0359(10) Uani 1 1 d . . . C2 C 0.7370(5) 0.6966(4) 0.38699(17) 0.0343(10) Uani 1 1 d . . . C3 C 0.7546(5) 0.8167(4) 0.42064(18) 0.0335(10) Uani 1 1 d . . . C4 C 0.6689(5) 0.7911(4) 0.47435(17) 0.0320(10) Uani 1 1 d . . . C7 C 0.9007(5) 0.6274(4) 0.37830(17) 0.0346(10) Uani 1 1 d . . . C8 C 0.6490(5) 0.7303(4) 0.32966(17) 0.0340(10) Uani 1 1 d . . . C9 C 0.8396(5) 0.9383(4) 0.40768(18) 0.0376(11) Uani 1 1 d . . . C10 C 0.8367(5) 1.0296(4) 0.44799(19) 0.0395(11) Uani 1 1 d . . . H10A H 0.8964 1.1123 0.4395 0.047 Uiso 1 1 calc R . . C11 C 0.7473(5) 1.0001(4) 0.50031(19) 0.0378(11) Uani 1 1 d . . . C12 C 0.6620(5) 0.8783(4) 0.51538(18) 0.0380(11) Uani 1 1 d . . . H12A H 0.6025 0.8571 0.5520 0.046 Uiso 1 1 calc R . . C13 C 1.0465(5) 1.0586(4) 0.3439(2) 0.0562(14) Uani 1 1 d . . . H13A H 1.1022 1.0540 0.3055 0.084 Uiso 1 1 calc R . . H13B H 1.1246 1.0401 0.3748 0.084 Uiso 1 1 calc R . . H13C H 1.0000 1.1497 0.3445 0.084 Uiso 1 1 calc R . . C14 C 0.8082(5) 1.2174(4) 0.5286(2) 0.0542(13) Uani 1 1 d . . . H14A H 0.7859 1.2696 0.5613 0.081 Uiso 1 1 calc R . . H14B H 0.7635 1.2659 0.4929 0.081 Uiso 1 1 calc R . . H14C H 0.9260 1.2069 0.5223 0.081 Uiso 1 1 calc R . . C15 C 0.9556(5) 0.5217(4) 0.41851(19) 0.0424(11) Uani 1 1 d . . . H15A H 0.8871 0.4872 0.4517 0.051 Uiso 1 1 calc R . . C16 C 1.1066(6) 0.4658(5) 0.4113(2) 0.0579(14) Uani 1 1 d . . . H16A H 1.1400 0.3924 0.4393 0.070 Uiso 1 1 calc R . . C17 C 1.2109(6) 0.5137(5) 0.3644(2) 0.0547(13) Uani 1 1 d . . . H17A H 1.3164 0.4756 0.3601 0.066 Uiso 1 1 calc R . . C18 C 1.1581(6) 0.6185(5) 0.3238(2) 0.0550(13) Uani 1 1 d . . . H18A H 1.2278 0.6527 0.2909 0.066 Uiso 1 1 calc R . . C19 C 1.0058(5) 0.6744(4) 0.33030(19) 0.0454(12) Uani 1 1 d . . . H19B H 0.9717 0.7461 0.3016 0.054 Uiso 1 1 calc R . . C20 C 0.6352(5) 0.6324(4) 0.29274(18) 0.0373(10) Uani 1 1 d . . . H20A H 0.6804 0.5444 0.3033 0.045 Uiso 1 1 calc R . . C21 C 0.5565(5) 0.6612(4) 0.24073(19) 0.0418(11) Uani 1 1 d . . . H21A H 0.5467 0.5919 0.2165 0.050 Uiso 1 1 calc R . . C22 C 0.4918(5) 0.7887(4) 0.22335(19) 0.0430(11) Uani 1 1 d . . . C23 C 0.5024(5) 0.8840(4) 0.2606(2) 0.0543(13) Uani 1 1 d . . . H23B H 0.4555 0.9713 0.2501 0.065 Uiso 1 1 calc R . . C24 C 0.5789(5) 0.8573(4) 0.3128(2) 0.0478(12) Uani 1 1 d . . . H24B H 0.5840 0.9261 0.3375 0.057 Uiso 1 1 calc R . . C25 C 0.4118(6) 0.8214(5) 0.1655(2) 0.0730(16) Uani 1 1 d . . . H25A H 0.4646 0.9011 0.1422 0.109 Uiso 1 1 calc R . . H25B H 0.2963 0.8410 0.1728 0.109 Uiso 1 1 calc R . . H25C H 0.4226 0.7432 0.1438 0.109 Uiso 1 1 calc R . . O4 O 0.9618(3) 0.8865(3) 0.83510(13) 0.0457(8) Uani 1 1 d . . . O5 O 0.7598(3) 1.0974(3) 1.00273(13) 0.0477(8) Uani 1 1 d . . . O6 O 0.5699(3) 0.4594(2) 0.92749(12) 0.0404(7) Uani 1 1 d . . . N2 N 0.5844(4) 0.6578(3) 0.96744(16) 0.0358(9) Uani 1 1 d . . . H2 H 0.522(4) 0.638(4) 1.0026(16) 0.037(12) Uiso 1 1 d . . . C31 C 0.6200(5) 0.5765(4) 0.92639(17) 0.0334(10) Uani 1 1 d . . . C32 C 0.7324(5) 0.6539(4) 0.87671(17) 0.0331(10) Uani 1 1 d . . . C33 C 0.7642(5) 0.7834(4) 0.90256(17) 0.0328(10) Uani 1 1 d . . . C34 C 0.6713(5) 0.7818(4) 0.95457(18) 0.0354(10) Uani 1 1 d . . . C37 C 0.8813(5) 0.5637(4) 0.87191(17) 0.0330(10) Uani 1 1 d . . . C38 C 0.6341(5) 0.6838(4) 0.82167(18) 0.0358(10) Uani 1 1 d . . . C39 C 0.8675(5) 0.8914(4) 0.88510(18) 0.0351(10) Uani 1 1 d . . . C40 C 0.8713(5) 0.9984(4) 0.91874(18) 0.0376(11) Uani 1 1 d . . . H40A H 0.9436 1.0728 0.9073 0.045 Uiso 1 1 calc R . . C41 C 0.7691(5) 0.9952(4) 0.96878(19) 0.0387(11) Uani 1 1 d . . . C42 C 0.6689(5) 0.8849(4) 0.98832(18) 0.0377(11) Uani 1 1 d . . . H42A H 0.6017 0.8810 1.0234 0.045 Uiso 1 1 calc R . . C43 C 1.0856(6) 0.9862(4) 0.8202(2) 0.0702(17) Uani 1 1 d . . . H43A H 1.1434 0.9710 0.7833 0.105 Uiso 1 1 calc R . . H43B H 1.1624 0.9792 0.8516 0.105 Uiso 1 1 calc R . . H43C H 1.0366 1.0772 0.8153 0.105 Uiso 1 1 calc R . . C44 C 0.8500(5) 1.2187(4) 0.98322(19) 0.0499(12) Uani 1 1 d . . . H44A H 0.8215 1.2872 1.0089 0.075 Uiso 1 1 calc R . . H44B H 0.8239 1.2538 0.9428 0.075 Uiso 1 1 calc R . . H44C H 0.9666 1.1988 0.9846 0.075 Uiso 1 1 calc R . . C45 C 0.9971(5) 0.5597(4) 0.91316(19) 0.0455(12) Uani 1 1 d . . . H45A H 0.9866 0.6190 0.9422 0.055 Uiso 1 1 calc R . . C46 C 1.1268(5) 0.4728(5) 0.9136(2) 0.0496(12) Uani 1 1 d . . . H46A H 1.2035 0.4717 0.9431 0.059 Uiso 1 1 calc R . . C47 C 1.1477(6) 0.3867(5) 0.8717(2) 0.0512(12) Uani 1 1 d . . . H47A H 1.2386 0.3270 0.8716 0.061 Uiso 1 1 calc R . . C48 C 1.0337(6) 0.3898(4) 0.8305(2) 0.0536(13) Uani 1 1 d . . . H48A H 1.0458 0.3311 0.8012 0.064 Uiso 1 1 calc R . . C49 C 0.9015(5) 0.4759(4) 0.83019(18) 0.0427(11) Uani 1 1 d . . . H49A H 0.8235 0.4751 0.8012 0.051 Uiso 1 1 calc R . . C50 C 0.7107(5) 0.7215(4) 0.76635(18) 0.0418(11) Uani 1 1 d . . . H50A H 0.8259 0.7289 0.7626 0.050 Uiso 1 1 calc R . . C51 C 0.6213(6) 0.7480(4) 0.71722(19) 0.0453(12) Uani 1 1 d . . . H51A H 0.6769 0.7736 0.6801 0.054 Uiso 1 1 calc R . . C52 C 0.4545(6) 0.7388(4) 0.7198(2) 0.0419(11) Uani 1 1 d . . . C53 C 0.3778(5) 0.7046(4) 0.7747(2) 0.0474(12) Uani 1 1 d . . . H53A H 0.2625 0.6992 0.7783 0.057 Uiso 1 1 calc R . . C54 C 0.4663(5) 0.6781(4) 0.8244(2) 0.0452(11) Uani 1 1 d . . . H54A H 0.4101 0.6553 0.8616 0.054 Uiso 1 1 calc R . . C55 C 0.3598(6) 0.7620(5) 0.6664(2) 0.0651(15) Uani 1 1 d . . . H55A H 0.3870 0.8516 0.6443 0.098 Uiso 1 1 calc R . . H55B H 0.2433 0.7586 0.6778 0.098 Uiso 1 1 calc R . . H55C H 0.3862 0.6912 0.6417 0.098 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 O1 0.058(2) 0.0420(18) 0.046(2) -0.0003(15) 0.0042(16) -0.0262(15) O2 0.067(2) 0.0307(16) 0.054(2) -0.0147(15) -0.0141(17) -0.0058(15) O3 0.0511(19) 0.0273(16) 0.0447(18) -0.0056(13) 0.0020(15) -0.0162(13) N1 0.039(2) 0.0300(19) 0.035(2) -0.0064(17) 0.0059(18) -0.0064(16) C1 0.033(3) 0.032(2) 0.042(3) -0.002(2) 0.000(2) -0.0064(19) C2 0.040(3) 0.027(2) 0.036(2) -0.0010(18) 0.001(2) -0.0109(19) C3 0.033(2) 0.029(2) 0.038(3) -0.0030(19) -0.004(2) -0.0050(18) C4 0.031(2) 0.027(2) 0.038(3) -0.0037(19) -0.005(2) -0.0050(18) C7 0.036(3) 0.032(2) 0.037(3) -0.009(2) -0.003(2) -0.0084(19) C8 0.034(3) 0.026(2) 0.040(3) -0.0007(19) 0.001(2) -0.0068(18) C9 0.041(3) 0.030(2) 0.041(3) -0.003(2) -0.005(2) -0.008(2) C10 0.041(3) 0.032(2) 0.046(3) -0.001(2) -0.011(2) -0.0084(19) C11 0.041(3) 0.030(2) 0.045(3) -0.011(2) -0.016(2) -0.0012(19) C12 0.040(3) 0.034(2) 0.039(3) -0.002(2) -0.004(2) -0.0028(19) C13 0.052(3) 0.050(3) 0.063(3) 0.005(2) -0.003(3) -0.027(2) C14 0.058(3) 0.030(2) 0.079(4) -0.019(2) -0.017(3) -0.007(2) C15 0.048(3) 0.032(2) 0.047(3) -0.004(2) -0.004(2) -0.001(2) C16 0.059(4) 0.045(3) 0.073(4) -0.014(3) -0.017(3) 0.009(3) C17 0.045(3) 0.057(3) 0.068(4) -0.027(3) -0.013(3) 0.007(3) C18 0.042(3) 0.069(4) 0.058(3) -0.023(3) 0.003(3) -0.007(3) C19 0.049(3) 0.047(3) 0.041(3) -0.006(2) -0.002(2) -0.009(2) C20 0.040(3) 0.032(2) 0.040(3) -0.0027(19) -0.005(2) -0.0029(19) C21 0.044(3) 0.042(3) 0.042(3) -0.014(2) -0.003(2) -0.004(2) C22 0.042(3) 0.040(3) 0.048(3) -0.002(2) -0.013(2) -0.006(2) C23 0.059(3) 0.030(3) 0.075(4) -0.005(2) -0.026(3) -0.002(2) C24 0.059(3) 0.034(3) 0.053(3) -0.012(2) -0.015(3) -0.007(2) C25 0.089(4) 0.061(3) 0.071(4) -0.006(3) -0.036(3) 0.000(3) O4 0.056(2) 0.0319(16) 0.0488(19) -0.0072(14) 0.0116(16) -0.0195(14) O5 0.052(2) 0.0325(16) 0.061(2) -0.0185(15) 0.0010(16) -0.0094(14) O6 0.0460(18) 0.0282(16) 0.0469(18) -0.0076(13) 0.0055(14) -0.0130(13) N2 0.043(2) 0.0277(19) 0.036(2) -0.0057(17) 0.0068(18) -0.0107(16) C31 0.034(3) 0.030(2) 0.037(3) -0.006(2) -0.005(2) -0.0055(19) C32 0.038(3) 0.025(2) 0.036(2) -0.0042(18) 0.002(2) -0.0098(19) C33 0.037(3) 0.024(2) 0.037(3) -0.0051(18) 0.000(2) -0.0042(18) C34 0.035(3) 0.028(2) 0.042(3) -0.003(2) -0.004(2) -0.0049(18) C37 0.036(3) 0.022(2) 0.040(3) -0.0038(19) 0.003(2) -0.0073(18) C38 0.041(3) 0.024(2) 0.044(3) -0.0092(19) -0.002(2) -0.0061(18) C39 0.037(3) 0.031(2) 0.037(3) -0.0046(19) -0.004(2) -0.0057(19) C40 0.040(3) 0.027(2) 0.047(3) -0.005(2) -0.006(2) -0.0077(19) C41 0.044(3) 0.026(2) 0.050(3) -0.012(2) -0.015(2) -0.0005(19) C42 0.039(3) 0.032(2) 0.043(3) -0.009(2) 0.001(2) -0.0053(19) C43 0.076(4) 0.044(3) 0.091(4) -0.024(3) 0.038(3) -0.034(3) C44 0.060(3) 0.033(2) 0.059(3) -0.010(2) -0.011(3) -0.007(2) C45 0.047(3) 0.044(3) 0.049(3) -0.015(2) -0.011(2) -0.006(2) C46 0.035(3) 0.052(3) 0.061(3) -0.003(3) -0.010(2) -0.003(2) C47 0.049(3) 0.051(3) 0.051(3) 0.000(2) 0.005(3) 0.006(2) C48 0.066(4) 0.047(3) 0.048(3) -0.011(2) 0.007(3) 0.012(3) C49 0.047(3) 0.040(3) 0.042(3) -0.009(2) -0.005(2) -0.001(2) C50 0.043(3) 0.041(3) 0.041(3) -0.002(2) -0.005(2) -0.011(2) C51 0.057(3) 0.038(3) 0.039(3) 0.003(2) -0.002(2) -0.011(2) C52 0.052(3) 0.026(2) 0.049(3) -0.007(2) -0.015(3) -0.003(2) C53 0.040(3) 0.046(3) 0.058(3) -0.010(2) -0.008(3) -0.001(2) C54 0.042(3) 0.046(3) 0.048(3) -0.009(2) -0.003(2) -0.007(2) C55 0.068(4) 0.056(3) 0.070(4) -0.002(3) -0.019(3) 0.000(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 O1 C9 1.360(5) . ? O1 C13 1.426(4) . ? O2 C11 1.378(5) . ? O2 C14 1.425(4) . ? O3 C1 1.216(4) . ? N1 C1 1.349(5) . ? N1 C4 1.404(4) . ? N1 H1 0.94(4) . ? C1 C2 1.544(5) . ? C2 C3 1.521(5) . ? C2 C7 1.524(5) . ? C2 C8 1.532(5) . ? C3 C4 1.382(5) . ? C3 C9 1.385(5) . ? C4 C12 1.366(5) . ? C7 C15 1.386(5) . ? C7 C19 1.394(5) . ? C8 C20 1.386(5) . ? C8 C24 1.394(5) . ? C9 C10 1.383(5) . ? C10 C11 1.373(5) . ? C10 H10A 0.9500 . ? C11 C12 1.393(5) . ? C12 H12A 0.9500 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C16 1.369(6) . ? C15 H15A 0.9500 . ? C16 C17 1.374(6) . ? C16 H16A 0.9500 . ? C17 C18 1.379(6) . ? C17 H17A 0.9500 . ? C18 C19 1.376(6) . ? C18 H18A 0.9500 . ? C19 H19B 0.9500 . ? C20 C21 1.383(5) . ? C20 H20A 0.9500 . ? C21 C22 1.382(5) . ? C21 H21A 0.9500 . ? C22 C23 1.369(6) . ? C22 C25 1.509(6) . ? C23 C24 1.376(6) . ? C23 H23B 0.9500 . ? C24 H24B 0.9500 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? O4 C39 1.360(4) . ? O4 C43 1.420(4) . ? O5 C41 1.364(4) . ? O5 C44 1.423(4) . ? O6 C31 1.231(4) . ? N2 C31 1.346(5) . ? N2 C34 1.413(5) . ? N2 H2 0.93(4) . ? C31 C32 1.549(5) . ? C32 C33 1.519(5) . ? C32 C37 1.521(5) . ? C32 C38 1.530(5) . ? C33 C39 1.373(5) . ? C33 C34 1.384(5) . ? C34 C42 1.368(5) . ? C37 C45 1.376(5) . ? C37 C49 1.387(5) . ? C38 C54 1.380(5) . ? C38 C50 1.393(5) . ? C39 C40 1.400(5) . ? C40 C41 1.386(5) . ? C40 H40A 0.9500 . ? C41 C42 1.383(5) . ? C42 H42A 0.9500 . ? C43 H43A 0.9800 . ? C43 H43B 0.9800 . ? C43 H43C 0.9800 . ? C44 H44A 0.9800 . ? C44 H44B 0.9800 . ? C44 H44C 0.9800 . ? C45 C46 1.366(6) . ? C45 H45A 0.9500 . ? C46 C47 1.377(6) . ? C46 H46A 0.9500 . ? C47 C48 1.367(6) . ? C47 H47A 0.9500 . ? C48 C49 1.378(6) . ? C48 H48A 0.9500 . ? C49 H49A 0.9500 . ? C50 C51 1.373(5) . ? C50 H50A 0.9500 . ? C51 C52 1.374(6) . ? C51 H51A 0.9500 . ? C52 C53 1.382(6) . ? C52 C55 1.478(6) . ? C53 C54 1.380(6) . ? C53 H53A 0.9500 . ? C54 H54A 0.9500 . ? C55 H55A 0.9800 . ? C55 H55B 0.9800 . ? C55 H55C 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 C9 O1 C13 118.7(3) . . ? C11 O2 C14 117.8(3) . . ? C1 N1 C4 111.8(3) . . ? C1 N1 H1 127(2) . . ? C4 N1 H1 121(2) . . ? O3 C1 N1 125.2(4) . . ? O3 C1 C2 126.0(4) . . ? N1 C1 C2 108.8(3) . . ? C3 C2 C7 110.8(3) . . ? C3 C2 C8 114.3(3) . . ? C7 C2 C8 112.7(3) . . ? C3 C2 C1 100.6(3) . . ? C7 C2 C1 109.3(3) . . ? C8 C2 C1 108.4(3) . . ? C4 C3 C9 117.9(4) . . ? C4 C3 C2 109.7(3) . . ? C9 C3 C2 132.4(4) . . ? C12 C4 C3 124.2(3) . . ? C12 C4 N1 126.7(4) . . ? C3 C4 N1 109.1(3) . . ? C15 C7 C19 117.2(4) . . ? C15 C7 C2 122.4(4) . . ? C19 C7 C2 120.4(4) . . ? C20 C8 C24 117.6(4) . . ? C20 C8 C2 120.1(3) . . ? C24 C8 C2 122.4(3) . . ? O1 C9 C10 124.5(3) . . ? O1 C9 C3 115.6(4) . . ? C10 C9 C3 119.9(4) . . ? C11 C10 C9 119.8(4) . . ? C11 C10 H10A 120.1 . . ? C9 C10 H10A 120.1 . . ? C10 C11 O2 123.7(3) . . ? C10 C11 C12 122.1(4) . . ? O2 C11 C12 114.2(4) . . ? C4 C12 C11 116.0(4) . . ? C4 C12 H12A 122.0 . . ? C11 C12 H12A 122.0 . . ? O1 C13 H13A 109.5 . . ? O1 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O1 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O2 C14 H14A 109.5 . . ? O2 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? O2 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C16 C15 C7 121.3(4) . . ? C16 C15 H15A 119.4 . . ? C7 C15 H15A 119.4 . . ? C15 C16 C17 121.5(5) . . ? C15 C16 H16A 119.3 . . ? C17 C16 H16A 119.3 . . ? C16 C17 C18 118.0(5) . . ? C16 C17 H17A 121.0 . . ? C18 C17 H17A 121.0 . . ? C19 C18 C17 121.0(5) . . ? C19 C18 H18A 119.5 . . ? C17 C18 H18A 119.5 . . ? C18 C19 C7 121.0(4) . . ? C18 C19 H19B 119.5 . . ? C7 C19 H19B 119.5 . . ? C21 C20 C8 120.8(4) . . ? C21 C20 H20A 119.6 . . ? C8 C20 H20A 119.6 . . ? C22 C21 C20 121.3(4) . . ? C22 C21 H21A 119.3 . . ? C20 C21 H21A 119.3 . . ? C23 C22 C21 117.6(4) . . ? C23 C22 C25 121.2(4) . . ? C21 C22 C25 121.2(4) . . ? C22 C23 C24 122.1(4) . . ? C22 C23 H23B 119.0 . . ? C24 C23 H23B 119.0 . . ? C23 C24 C8 120.5(4) . . ? C23 C24 H24B 119.7 . . ? C8 C24 H24B 119.7 . . ? C22 C25 H25A 109.5 . . ? C22 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C22 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C39 O4 C43 118.1(3) . . ? C41 O5 C44 118.2(3) . . ? C31 N2 C34 110.7(4) . . ? C31 N2 H2 128(2) . . ? C34 N2 H2 121(2) . . ? O6 C31 N2 125.6(4) . . ? O6 C31 C32 125.0(4) . . ? N2 C31 C32 109.4(3) . . ? C33 C32 C37 114.0(3) . . ? C33 C32 C38 111.1(3) . . ? C37 C32 C38 116.3(3) . . ? C33 C32 C31 100.5(3) . . ? C37 C32 C31 105.5(3) . . ? C38 C32 C31 107.8(3) . . ? C39 C33 C34 118.3(3) . . ? C39 C33 C32 132.4(4) . . ? C34 C33 C32 109.2(3) . . ? C42 C34 C33 124.1(4) . . ? C42 C34 N2 126.1(4) . . ? C33 C34 N2 109.8(3) . . ? C45 C37 C49 117.3(4) . . ? C45 C37 C32 119.4(4) . . ? C49 C37 C32 123.1(4) . . ? C54 C38 C50 116.8(4) . . ? C54 C38 C32 122.0(4) . . ? C50 C38 C32 121.1(4) . . ? O4 C39 C33 116.6(3) . . ? O4 C39 C40 123.8(3) . . ? C33 C39 C40 119.6(4) . . ? C41 C40 C39 119.7(3) . . ? C41 C40 H40A 120.1 . . ? C39 C40 H40A 120.1 . . ? O5 C41 C42 114.8(4) . . ? O5 C41 C40 123.7(3) . . ? C42 C41 C40 121.6(4) . . ? C34 C42 C41 116.6(4) . . ? C34 C42 H42A 121.7 . . ? C41 C42 H42A 121.7 . . ? O4 C43 H43A 109.5 . . ? O4 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? O4 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? O5 C44 H44A 109.5 . . ? O5 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? O5 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? C46 C45 C37 121.8(4) . . ? C46 C45 H45A 119.1 . . ? C37 C45 H45A 119.1 . . ? C45 C46 C47 120.9(4) . . ? C45 C46 H46A 119.6 . . ? C47 C46 H46A 119.6 . . ? C48 C47 C46 117.9(4) . . ? C48 C47 H47A 121.1 . . ? C46 C47 H47A 121.1 . . ? C47 C48 C49 121.6(4) . . ? C47 C48 H48A 119.2 . . ? C49 C48 H48A 119.2 . . ? C48 C49 C37 120.5(4) . . ? C48 C49 H49A 119.7 . . ? C37 C49 H49A 119.7 . . ? C51 C50 C38 120.7(4) . . ? C51 C50 H50A 119.7 . . ? C38 C50 H50A 119.7 . . ? C50 C51 C52 122.5(4) . . ? C50 C51 H51A 118.8 . . ? C52 C51 H51A 118.8 . . ? C51 C52 C53 117.1(4) . . ? C51 C52 C55 122.1(4) . . ? C53 C52 C55 120.8(4) . . ? C54 C53 C52 121.0(4) . . ? C54 C53 H53A 119.5 . . ? C52 C53 H53A 119.5 . . ? C53 C54 C38 121.9(4) . . ? C53 C54 H54A 119.0 . . ? C38 C54 H54A 119.0 . . ? C52 C55 H55A 109.5 . . ? C52 C55 H55B 109.5 . . ? H55A C55 H55B 109.5 . . ? C52 C55 H55C 109.5 . . ? H55A C55 H55C 109.5 . . ? H55B C55 H55C 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 C4 N1 C1 O3 178.2(4) . . . . ? C4 N1 C1 C2 -1.3(5) . . . . ? O3 C1 C2 C3 -178.9(4) . . . . ? N1 C1 C2 C3 0.6(4) . . . . ? O3 C1 C2 C7 -62.3(5) . . . . ? N1 C1 C2 C7 117.2(4) . . . . ? O3 C1 C2 C8 60.9(5) . . . . ? N1 C1 C2 C8 -119.6(4) . . . . ? C7 C2 C3 C4 -115.2(4) . . . . ? C8 C2 C3 C4 116.2(4) . . . . ? C1 C2 C3 C4 0.3(4) . . . . ? C7 C2 C3 C9 63.3(6) . . . . ? C8 C2 C3 C9 -65.3(6) . . . . ? C1 C2 C3 C9 178.8(4) . . . . ? C9 C3 C4 C12 0.3(6) . . . . ? C2 C3 C4 C12 179.1(4) . . . . ? C9 C3 C4 N1 -179.8(4) . . . . ? C2 C3 C4 N1 -1.1(5) . . . . ? C1 N1 C4 C12 -178.6(4) . . . . ? C1 N1 C4 C3 1.5(5) . . . . ? C3 C2 C7 C15 90.0(4) . . . . ? C8 C2 C7 C15 -140.6(4) . . . . ? C1 C2 C7 C15 -20.0(5) . . . . ? C3 C2 C7 C19 -86.5(4) . . . . ? C8 C2 C7 C19 43.0(4) . . . . ? C1 C2 C7 C19 163.5(3) . . . . ? C3 C2 C8 C20 175.4(3) . . . . ? C7 C2 C8 C20 47.8(5) . . . . ? C1 C2 C8 C20 -73.3(5) . . . . ? C3 C2 C8 C24 -5.3(5) . . . . ? C7 C2 C8 C24 -132.9(4) . . . . ? C1 C2 C8 C24 106.0(4) . . . . ? C13 O1 C9 C10 19.5(6) . . . . ? C13 O1 C9 C3 -161.5(4) . . . . ? C4 C3 C9 O1 -179.1(4) . . . . ? C2 C3 C9 O1 2.5(7) . . . . ? C4 C3 C9 C10 0.0(6) . . . . ? C2 C3 C9 C10 -178.4(4) . . . . ? O1 C9 C10 C11 177.8(4) . . . . ? C3 C9 C10 C11 -1.1(6) . . . . ? C9 C10 C11 O2 -178.4(4) . . . . ? C9 C10 C11 C12 2.0(6) . . . . ? C14 O2 C11 C10 4.9(6) . . . . ? C14 O2 C11 C12 -175.5(3) . . . . ? C3 C4 C12 C11 0.5(6) . . . . ? N1 C4 C12 C11 -179.3(4) . . . . ? C10 C11 C12 C4 -1.6(6) . . . . ? O2 C11 C12 C4 178.7(4) . . . . ? C19 C7 C15 C16 0.0(6) . . . . ? C2 C7 C15 C16 -176.6(4) . . . . ? C7 C15 C16 C17 1.0(7) . . . . ? C15 C16 C17 C18 -1.3(7) . . . . ? C16 C17 C18 C19 0.5(6) . . . . ? C17 C18 C19 C7 0.5(6) . . . . ? C15 C7 C19 C18 -0.7(6) . . . . ? C2 C7 C19 C18 175.9(4) . . . . ? C24 C8 C20 C21 0.9(6) . . . . ? C2 C8 C20 C21 -179.8(4) . . . . ? C8 C20 C21 C22 1.2(6) . . . . ? C20 C21 C22 C23 -2.6(6) . . . . ? C20 C21 C22 C25 177.6(4) . . . . ? C21 C22 C23 C24 2.1(7) . . . . ? C25 C22 C23 C24 -178.1(4) . . . . ? C22 C23 C24 C8 -0.1(7) . . . . ? C20 C8 C24 C23 -1.4(6) . . . . ? C2 C8 C24 C23 179.3(4) . . . . ? C34 N2 C31 O6 175.8(4) . . . . ? C34 N2 C31 C32 -5.0(4) . . . . ? O6 C31 C32 C33 -174.7(4) . . . . ? N2 C31 C32 C33 6.1(4) . . . . ? O6 C31 C32 C37 -55.9(5) . . . . ? N2 C31 C32 C37 124.9(3) . . . . ? O6 C31 C32 C38 68.9(5) . . . . ? N2 C31 C32 C38 -110.2(4) . . . . ? C37 C32 C33 C39 59.7(6) . . . . ? C38 C32 C33 C39 -74.1(6) . . . . ? C31 C32 C33 C39 172.0(4) . . . . ? C37 C32 C33 C34 -117.5(4) . . . . ? C38 C32 C33 C34 108.7(4) . . . . ? C31 C32 C33 C34 -5.2(4) . . . . ? C39 C33 C34 C42 3.8(6) . . . . ? C32 C33 C34 C42 -178.5(4) . . . . ? C39 C33 C34 N2 -174.9(4) . . . . ? C32 C33 C34 N2 2.7(5) . . . . ? C31 N2 C34 C42 -177.2(4) . . . . ? C31 N2 C34 C33 1.5(5) . . . . ? C33 C32 C37 C45 32.5(5) . . . . ? C38 C32 C37 C45 163.8(3) . . . . ? C31 C32 C37 C45 -76.8(4) . . . . ? C33 C32 C37 C49 -152.6(4) . . . . ? C38 C32 C37 C49 -21.3(5) . . . . ? C31 C32 C37 C49 98.1(4) . . . . ? C33 C32 C38 C54 -91.5(4) . . . . ? C37 C32 C38 C54 135.8(4) . . . . ? C31 C32 C38 C54 17.6(5) . . . . ? C33 C32 C38 C50 86.9(4) . . . . ? C37 C32 C38 C50 -45.8(5) . . . . ? C31 C32 C38 C50 -163.9(3) . . . . ? C43 O4 C39 C33 -171.4(4) . . . . ? C43 O4 C39 C40 8.4(6) . . . . ? C34 C33 C39 O4 177.3(4) . . . . ? C32 C33 C39 O4 0.3(7) . . . . ? C34 C33 C39 C40 -2.5(6) . . . . ? C32 C33 C39 C40 -179.5(4) . . . . ? O4 C39 C40 C41 179.2(4) . . . . ? C33 C39 C40 C41 -1.0(6) . . . . ? C44 O5 C41 C42 -175.4(4) . . . . ? C44 O5 C41 C40 5.3(6) . . . . ? C39 C40 C41 O5 -177.2(4) . . . . ? C39 C40 C41 C42 3.5(6) . . . . ? C33 C34 C42 C41 -1.4(6) . . . . ? N2 C34 C42 C41 177.2(4) . . . . ? O5 C41 C42 C34 178.3(3) . . . . ? C40 C41 C42 C34 -2.4(6) . . . . ? C49 C37 C45 C46 -0.3(6) . . . . ? C32 C37 C45 C46 174.9(4) . . . . ? C37 C45 C46 C47 1.0(7) . . . . ? C45 C46 C47 C48 -0.9(6) . . . . ? C46 C47 C48 C49 0.1(7) . . . . ? C47 C48 C49 C37 0.7(7) . . . . ? C45 C37 C49 C48 -0.5(6) . . . . ? C32 C37 C49 C48 -175.5(4) . . . . ? C54 C38 C50 C51 -1.6(6) . . . . ? C32 C38 C50 C51 179.9(4) . . . . ? C38 C50 C51 C52 -0.1(6) . . . . ? C50 C51 C52 C53 1.6(6) . . . . ? C50 C51 C52 C55 -177.5(4) . . . . ? C51 C52 C53 C54 -1.4(6) . . . . ? C55 C52 C53 C54 177.7(4) . . . . ? C52 C53 C54 C38 -0.3(6) . . . . ? C50 C38 C54 C53 1.8(6) . . . . ? C32 C38 C54 C53 -179.7(4) . . . . ? 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 O3 0.94(4) 1.92(4) 2.824(4) 162(3) 2_666 N2 H2 O6 0.93(4) 1.88(4) 2.776(4) 161(3) 2_667 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.306 _refine_diff_density_min -0.230 _refine_diff_density_rms 0.050 _database_code_depnum_ccdc_archive 'CCDC 937923' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_8 _vrf_PLAT340_jonjk63 ; PROBLEM: _C Low Bond Precision on C-C Bonds ............... 0.0088 Ang RESPONSE: Due to the exact distribution of the disordered groups, the refinement had to be performed in chiral space group P2(1), despite significant pseudosymmetric effects and worse overall statistics. Thus, while a refinement in centrosymmetric space group P2(1)/c offered an average C-C bond precision of 0.0033 \%A, the disorder ratios were inconsistent with symmetry elements that required a 1:1 ratio, and any constraining to a 1:1 ratio provided a forced and unrealistic model. ; _vrf_PLAT301_jonjk63 ; PROBLEM: _G Note: Main Residue Disorder ................... 23 Perc. RESPONSE: Phenyl group C7, C21-C25 on one independent molecule and methoxy group O8-C70 on the other independent molecule are modeled as disordered over two positions each (75:25). Initially the ratios of each were determined independently, which resulted in a common ratio. Further examination showed that the disorders had to be refined together to avoid any violation of van der Waals radii. Phenyl group C57, C71-C75 on one independent molecule and methoxy group O4-C20 on the other independent molecule are modeled as disordered over two positions (50:50 exactly, a requirement of the crystallographic two-fold screw axes). Independent refinements of these disorders also resulted in the 50:50 ratio. Additionally, methyl group C81 on one molecule is disordered (50:50, again a requirement of symmetry) over the two possible phenyl ring locations, while methyl group C31 only exists on one phenyl ring in the other molecule. ; _vrf_PLAT791_jonjk63 ; PROBLEM: _G Note: The Model has Chirality at C2 (Verify) .. R RESPONSE: The structure is a racemate. ; _vrf_PLAT860_jonjk63 ; PROBLEM: _G Note: Number of Least-Squares Restraints ....... 30 RESPONSE: Corresponding bond lengths and angles among the two orientations at each disorder site were restrained to be similar. Anisotropic displacement parameters for pairs of spatially close atoms were constrained to be equivalent. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common jonjk63 _chemical_melting_point ? _chemical_formula_moiety 'C31 H30 N2 O4' _chemical_formula_sum 'C31 H30 N2 O4' _chemical_formula_weight 494.57 _chemical_absolute_configuration . loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.6386(8) _cell_length_b 19.1068(13) _cell_length_c 11.7615(8) _cell_angle_alpha 90.00 _cell_angle_beta 94.728(1) _cell_angle_gamma 90.00 _cell_volume 2606.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100.0(5) _cell_measurement_reflns_used 4058 _cell_measurement_theta_min 2.60 _cell_measurement_theta_max 25.74 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.260 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1048 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9673 _exptl_absorpt_correction_T_max 0.9933 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100.0(5) _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 II CCD Platform' _diffrn_measurement_method 'area detector, \w scans per \f' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 37187 _diffrn_reflns_av_R_equivalents 0.0869 _diffrn_reflns_av_sigmaI/netI 0.0592 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 28.28 _reflns_number_total 6662 _reflns_number_gt 4153 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2011)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction 'SAINT (Bruker, 2009)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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. Due to the exact distribution of the disordered groups, the refinement had to be performed in chiral space group P2(1), despite significant pseudosymmetric effects and worse overall statistics. Thus, while a refinement in centrosymmetric space group P2(1)/c offered an average C-C bond precision of 0.0033 \%A, the disorder ratios were inconsistent with symmetry elements that required a 1:1 ratio, and any constraining to a 1:1 ratio provided a forced and unrealistic model. Phenyl group C7, C21-C25 on one independent molecule and methoxy group O8-C70 on the other independent molecule are modeled as disordered over two positions each (75:25). Initially the ratios of each were determined independently, which resulted in a common ratio. Further examination showed that the disorders had to be refined together to avoid any violation of van der Waals radii. Phenyl group C57, C71-C75 on one independent molecule and methoxy group O4-C20 on the other independent molecule are modeled as disordered over two positions (50:50 exactly, a requirement of the crystallographic two-fold screw axes). Independent refinements of these disorders also resulted in the 50:50 ratio. Additionally, methyl group C81 on one molecule is disordered (50:50, again a requirement of symmetry) over the two possible phenyl ring locations, while methyl group C31 only exists on one phenyl ring in the other molecule. Corresponding bond lengths and angles among the two orientations at each disorder site were restrained to be similar. Anisotropic displacement parameters for pairs of spatially close atoms were constrained to be equivalent. Amine hydrogen atoms were found from the difference Fourier map, and their positional parameters were refined independently from those of their respective bonded nitrogen atoms. Their isotropic displacement parameters were relative to those of the nitrogen atoms, such that Uiso[H] = 1.5*Ueq[N]. Due to the lack of significant anomalous scattering effects, all Friedel opposites were merged in the final refinement. ; _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^)+(0.0482P)^2^+1.0750P] 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_abs_structure_details # 'Flack H D (1983), Acta Cryst. A39, 876-881' #_refine_ls_abs_structure_Flack -2(2) _refine_ls_number_reflns 6662 _refine_ls_number_parameters 657 _refine_ls_number_restraints 30 _refine_ls_R_factor_all 0.1029 _refine_ls_R_factor_gt 0.0559 _refine_ls_wR_factor_ref 0.1372 _refine_ls_wR_factor_gt 0.1155 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.021 _refine_ls_shift/su_max 0.008 _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 N1 N 0.4948(4) -0.0551(3) 0.1426(4) 0.0330(13) Uani 1 1 d . B . H1 H 0.494(5) -0.043(3) 0.073(5) 0.049 Uiso 1 1 d . . . N2 N 0.7090(4) -0.0886(3) 0.3667(4) 0.0257(4) Uani 1 1 d . B . H2 H 0.716(4) -0.132(3) 0.396(4) 0.039 Uiso 1 1 d . . . C1 C 0.5945(4) -0.0267(3) 0.2137(5) 0.0266(5) Uani 1 1 d D . . C2 C 0.5870(4) -0.0666(3) 0.3340(5) 0.0285(13) Uani 1 1 d . B . C3 C 0.5132(4) -0.1293(3) 0.2958(5) 0.0276(5) Uani 1 1 d . . . C4 C 0.4658(4) -0.1200(4) 0.1855(5) 0.0292(5) Uani 1 1 d . B . C5 C 0.7677(4) -0.0890(3) 0.2649(5) 0.0270(13) Uani 1 1 d . . . C6 C 0.7082(4) -0.0527(3) 0.1790(5) 0.0247(4) Uani 1 1 d . B . C9 C 0.4904(5) -0.1893(3) 0.3553(5) 0.0276(13) Uani 1 1 d . B . C10 C 0.4215(4) -0.2412(3) 0.3024(5) 0.0290(13) Uani 1 1 d . . . H10 H 0.4047 -0.2826 0.3427 0.035 Uiso 1 1 calc R B . C11 C 0.3774(5) -0.2321(4) 0.1899(5) 0.0336(15) Uani 1 1 d . B . C12 C 0.3975(4) -0.1717(4) 0.1287(5) 0.0318(5) Uani 1 1 d . . . H12 H 0.3665 -0.1657 0.0521 0.038 Uiso 1 1 calc R B . O1 O 0.5418(3) -0.1914(2) 0.4646(3) 0.0305(4) Uani 1 1 d . . . C13 C 0.5208(6) -0.2524(4) 0.5308(6) 0.0419(16) Uani 1 1 d . B . H13A H 0.5646 -0.2490 0.6054 0.063 Uiso 1 1 calc R . . H13B H 0.5452 -0.2942 0.4909 0.063 Uiso 1 1 calc R . . H13C H 0.4384 -0.2557 0.5413 0.063 Uiso 1 1 calc R . . O2 O 0.3125(4) -0.2871(3) 0.1476(4) 0.0399(11) Uani 1 1 d . . . C14 C 0.2882(6) -0.2925(4) 0.0285(5) 0.0600(10) Uani 1 1 d . B . H14A H 0.2489 -0.3369 0.0102 0.090 Uiso 1 1 calc R . . H14B H 0.3604 -0.2908 -0.0088 0.090 Uiso 1 1 calc R . . H14C H 0.2385 -0.2535 0.0013 0.090 Uiso 1 1 calc R . . C15 C 0.7595(4) -0.0409(3) 0.0773(5) 0.0261(5) Uani 1 1 d . . . C16 C 0.8643(5) -0.0699(3) 0.0613(5) 0.0302(13) Uani 1 1 d . A . H16 H 0.8985 -0.0642 -0.0086 0.036 Uiso 1 1 calc R . . C17 C 0.9199(5) -0.1084(4) 0.1515(7) 0.0428(17) Uani 1 1 d D . . C18 C 0.8753(5) -0.1196(3) 0.2540(5) 0.0332(14) Uani 1 1 d . A . H18 H 0.9145 -0.1463 0.3134 0.040 Uiso 1 1 calc R . . O3 O 0.6967(3) -0.0021(2) -0.0019(3) 0.0314(4) Uani 1 1 d . B . C19 C 0.7521(5) 0.0161(4) -0.1008(5) 0.0376(16) Uani 1 1 d . . . H19A H 0.7027 0.0483 -0.1479 0.056 Uiso 1 1 calc R B . H19B H 0.7658 -0.0262 -0.1447 0.056 Uiso 1 1 calc R . . H19C H 0.8258 0.0390 -0.0782 0.056 Uiso 1 1 calc R . . O4 O 1.0098(6) -0.1482(5) 0.1097(8) 0.036(2) Uani 0.50 1 d PD A 1 C20 C 1.0628(10) -0.1979(7) 0.1883(11) 0.045(2) Uani 0.50 1 d PD A 1 H20A H 1.1310 -0.2178 0.1568 0.068 Uiso 0.50 1 calc PR A 1 H20B H 1.0079 -0.2354 0.2012 0.068 Uiso 0.50 1 calc PR A 1 H20C H 1.0859 -0.1745 0.2608 0.068 Uiso 0.50 1 calc PR A 1 O4' O 1.0374(6) -0.1243(6) 0.1383(9) 0.036(2) Uani 0.50 1 d PD A 5 C20' C 1.1092(10) -0.1531(8) 0.2328(12) 0.045(2) Uani 0.50 1 d PD A 5 H20D H 1.1885 -0.1575 0.2114 0.068 Uiso 0.50 1 calc PR A 5 H20E H 1.0801 -0.1994 0.2522 0.068 Uiso 0.50 1 calc PR A 5 H20F H 1.1079 -0.1220 0.2989 0.068 Uiso 0.50 1 calc PR A 5 C7 C 0.5848(10) 0.0532(4) 0.219(2) 0.022(2) Uani 0.728(19) 1 d PD B 1 C21 C 0.4862(10) 0.0893(7) 0.1824(18) 0.036(2) Uani 0.728(19) 1 d PD B 1 H21 H 0.4196 0.0648 0.1520 0.043 Uiso 0.728(19) 1 calc PR B 1 C22 C 0.4850(10) 0.1617(6) 0.1899(14) 0.040(2) Uani 0.728(19) 1 d PD B 1 H22 H 0.4152 0.1863 0.1704 0.048 Uiso 0.728(19) 1 calc PR B 1 C23 C 0.5844(10) 0.1992(6) 0.2257(14) 0.036(3) Uani 0.728(19) 1 d PD B 1 H23 H 0.5851 0.2489 0.2252 0.043 Uiso 0.728(19) 1 calc PR B 1 C24 C 0.6813(10) 0.1615(6) 0.2618(15) 0.035(2) Uani 0.728(19) 1 d PD B 1 H24 H 0.7492 0.1859 0.2892 0.042 Uiso 0.728(19) 1 calc PR B 1 C25 C 0.6829(10) 0.0906(6) 0.2592(17) 0.027(2) Uani 0.728(19) 1 d PD B 1 H25 H 0.7513 0.0662 0.2848 0.033 Uiso 0.728(19) 1 calc PR B 1 C7' C 0.609(3) 0.0531(9) 0.224(6) 0.022(2) Uani 0.272(19) 1 d PD B 5 C21' C 0.512(3) 0.0915(18) 0.198(5) 0.036(2) Uani 0.272(19) 1 d PD B 5 H21' H 0.4393 0.0691 0.1818 0.043 Uiso 0.272(19) 1 calc PR B 5 C22' C 0.520(2) 0.1640(18) 0.197(4) 0.040(2) Uani 0.272(19) 1 d PD B 5 H22' H 0.4564 0.1911 0.1665 0.048 Uiso 0.272(19) 1 calc PR B 5 C23' C 0.621(3) 0.1972(16) 0.240(4) 0.036(3) Uani 0.272(19) 1 d PD B 5 H23' H 0.6243 0.2467 0.2446 0.043 Uiso 0.272(19) 1 calc PR B 5 C24' C 0.714(3) 0.1572(17) 0.275(5) 0.035(2) Uani 0.272(19) 1 d PD B 5 H24' H 0.7820 0.1794 0.3063 0.042 Uiso 0.272(19) 1 calc PR B 5 C25' C 0.711(3) 0.0862(17) 0.265(5) 0.027(2) Uani 0.272(19) 1 d PD B 5 H25' H 0.7782 0.0594 0.2866 0.033 Uiso 0.272(19) 1 calc PR B 5 C8 C 0.5397(5) -0.0243(3) 0.4281(5) 0.0296(5) Uani 1 1 d . . . C26 C 0.4222(5) -0.0221(4) 0.4364(6) 0.0406(6) Uani 1 1 d . B . H26 H 0.3712 -0.0483 0.3855 0.049 Uiso 1 1 calc R . . C27 C 0.3797(6) 0.0198(4) 0.5219(7) 0.0471(18) Uani 1 1 d . . . H27 H 0.2988 0.0209 0.5278 0.057 Uiso 1 1 calc R B . C28 C 0.4485(6) 0.0587(4) 0.5967(6) 0.0441(18) Uani 1 1 d . B . C29 C 0.5661(7) 0.0557(4) 0.5860(6) 0.0459(6) Uani 1 1 d . . . H29 H 0.6163 0.0827 0.6363 0.055 Uiso 1 1 calc R B . C30 C 0.6131(5) 0.0145(4) 0.5045(6) 0.0358(5) Uani 1 1 d . B . H30 H 0.6943 0.0127 0.5005 0.043 Uiso 1 1 calc R . . C31 C 0.3961(8) 0.1032(5) 0.6862(8) 0.084(3) Uani 1 1 d . . . H31A H 0.4577 0.1226 0.7386 0.126 Uiso 1 1 calc R B . H31B H 0.3453 0.0741 0.7290 0.126 Uiso 1 1 calc R . . H31C H 0.3515 0.1414 0.6487 0.126 Uiso 1 1 calc R . . N3 N 0.0011(4) 0.3120(3) 0.1415(5) 0.0296(12) Uani 1 1 d . C . H3 H 0.012(4) 0.315(3) 0.060(5) 0.044 Uiso 1 1 d . . . N4 N 0.2164(4) 0.3451(3) 0.3655(4) 0.0257(4) Uani 1 1 d . C . H4 H 0.222(4) 0.384(3) 0.419(4) 0.039 Uiso 1 1 d . . . C51 C 0.1010(4) 0.2841(3) 0.2146(5) 0.0266(5) Uani 1 1 d . . . C52 C 0.0951(4) 0.3258(3) 0.3337(5) 0.0236(12) Uani 1 1 d . C . C53 C 0.0216(4) 0.3862(3) 0.2948(5) 0.0276(5) Uani 1 1 d . . . C54 C -0.0252(4) 0.3783(4) 0.1831(5) 0.0292(5) Uani 1 1 d . C . C55 C 0.2766(4) 0.3462(3) 0.2694(5) 0.0237(12) Uani 1 1 d . . . C56 C 0.2161(4) 0.3095(3) 0.1805(5) 0.0247(4) Uani 1 1 d . C . C59 C 0.0001(4) 0.4473(4) 0.3536(5) 0.0281(13) Uani 1 1 d . C . C60 C -0.0671(4) 0.4994(4) 0.3017(5) 0.0344(15) Uani 1 1 d . . . H60 H -0.0825 0.5411 0.3416 0.041 Uiso 1 1 calc R C . C61 C -0.1126(4) 0.4893(4) 0.1878(5) 0.0313(14) Uani 1 1 d . C . C62 C -0.0934(4) 0.4294(4) 0.1279(5) 0.0318(5) Uani 1 1 d . . . H62 H -0.1255 0.4232 0.0517 0.038 Uiso 1 1 calc R C . O5 O 0.0525(3) 0.4526(2) 0.4612(3) 0.0305(4) Uani 1 1 d . . . C63 C 0.0316(6) 0.5132(4) 0.5247(6) 0.0436(17) Uani 1 1 d . C . H63A H 0.0694 0.5086 0.6019 0.065 Uiso 1 1 calc R . . H63B H -0.0516 0.5189 0.5289 0.065 Uiso 1 1 calc R . . H63C H 0.0625 0.5542 0.4874 0.065 Uiso 1 1 calc R . . O6 O -0.1764(3) 0.5456(3) 0.1436(4) 0.0417(12) Uani 1 1 d . . . C64 C -0.2240(6) 0.5373(4) 0.0259(5) 0.0600(10) Uani 1 1 d . C . H64A H -0.2611 0.5810 -0.0007 0.090 Uiso 1 1 calc R . . H64B H -0.2811 0.4995 0.0215 0.090 Uiso 1 1 calc R . . H64C H -0.1619 0.5257 -0.0223 0.090 Uiso 1 1 calc R . . C65 C 0.2679(4) 0.2974(3) 0.0800(5) 0.0261(5) Uani 1 1 d . . . C66 C 0.3774(4) 0.3235(3) 0.0685(5) 0.0295(13) Uani 1 1 d . B . H66A H 0.4139 0.3151 0.0005 0.035 Uiso 1 1 calc R . . C67 C 0.4333(5) 0.3615(4) 0.1554(6) 0.0341(14) Uani 1 1 d D . . C68 C 0.3856(5) 0.3724(3) 0.2592(5) 0.0326(14) Uani 1 1 d . B . H68A H 0.4266 0.3968 0.3201 0.039 Uiso 1 1 calc R . . O7 O 0.2052(3) 0.2572(2) -0.0004(3) 0.0314(4) Uani 1 1 d . C . C69 C 0.2608(6) 0.2385(4) -0.1015(6) 0.0430(17) Uani 1 1 d . . . H69A H 0.2090 0.2090 -0.1507 0.064 Uiso 1 1 calc R C . H69B H 0.3320 0.2128 -0.0795 0.064 Uiso 1 1 calc R . . H69C H 0.2791 0.2811 -0.1428 0.064 Uiso 1 1 calc R . . O8 O 0.5471(6) 0.3791(5) 0.1393(9) 0.039(2) Uani 0.728(19) 1 d PD B 1 C70 C 0.6146(11) 0.4090(9) 0.2336(12) 0.067(4) Uani 0.728(19) 1 d PD B 1 H70A H 0.6914 0.4206 0.2107 0.100 Uiso 0.728(19) 1 calc PR B 1 H70B H 0.6220 0.3752 0.2966 0.100 Uiso 0.728(19) 1 calc PR B 1 H70C H 0.5770 0.4515 0.2585 0.100 Uiso 0.728(19) 1 calc PR B 1 O8' O 0.5280(16) 0.3982(13) 0.122(2) 0.039(2) Uani 0.272(19) 1 d PD B 5 C70' C 0.576(3) 0.448(2) 0.202(3) 0.067(4) Uani 0.272(19) 1 d PD B 5 H70D H 0.6407 0.4720 0.1704 0.100 Uiso 0.272(19) 1 calc PR B 5 H70E H 0.6040 0.4237 0.2725 0.100 Uiso 0.272(19) 1 calc PR B 5 H70F H 0.5172 0.4821 0.2187 0.100 Uiso 0.272(19) 1 calc PR B 5 C57 C 0.0988(5) 0.2056(4) 0.2233(5) 0.0323(14) Uani 0.50 1 d PD C 1 C71 C 0.0112(18) 0.1573(7) 0.190(4) 0.035(3) Uani 0.50 1 d PD C 1 H71 H -0.0597 0.1745 0.1553 0.042 Uiso 0.50 1 calc PR C 1 C72 C 0.0239(12) 0.0849(7) 0.2066(14) 0.0401(16) Uani 0.50 1 d PD C 1 H72 H -0.0393 0.0546 0.1866 0.048 Uiso 0.50 1 calc PR C 1 C73 C 0.1255(12) 0.0578(7) 0.2507(14) 0.033(2) Uani 0.50 1 d PD C 1 C74 C 0.2143(15) 0.1019(7) 0.2882(16) 0.035(3) Uani 0.50 1 d PD C 1 H74 H 0.2837 0.0840 0.3253 0.042 Uiso 0.50 1 calc PR C 1 C75 C 0.1991(16) 0.1747(7) 0.270(3) 0.0401(16) Uani 0.50 1 d PD C 1 H75 H 0.2627 0.2045 0.2910 0.048 Uiso 0.50 1 calc PR C 1 C57' C 0.0988(5) 0.2056(4) 0.2233(5) 0.0323(14) Uani 0.50 1 d PD C 5 C71' C -0.0054(19) 0.1735(7) 0.185(5) 0.035(3) Uani 0.50 1 d PD C 5 H71' H -0.0702 0.2014 0.1604 0.042 Uiso 0.50 1 calc PR C 5 C72' C -0.0146(12) 0.1003(7) 0.1835(16) 0.0401(16) Uani 0.50 1 d PD C 5 H72' H -0.0843 0.0784 0.1546 0.048 Uiso 0.50 1 calc PR C 5 C73' C 0.0769(12) 0.0611(7) 0.2237(14) 0.033(2) Uani 0.50 1 d PD C 5 H73' H 0.0699 0.0116 0.2254 0.040 Uiso 0.50 1 calc PR C 5 C74' C 0.1810(14) 0.0920(7) 0.2624(17) 0.035(3) Uani 0.50 1 d PD C 5 H74' H 0.2458 0.0639 0.2862 0.042 Uiso 0.50 1 calc PR C 5 C75' C 0.1895(16) 0.1659(7) 0.266(3) 0.0401(16) Uani 0.50 1 d PD C 5 H75' H 0.2581 0.1877 0.2979 0.048 Uiso 0.50 1 calc PR C 5 C58 C 0.0462(5) 0.2822(3) 0.4263(5) 0.0296(5) Uani 1 1 d . . . C76 C -0.0722(5) 0.2771(4) 0.4345(6) 0.0406(6) Uani 1 1 d . C . H76A H -0.1218 0.3036 0.3826 0.049 Uiso 1 1 calc R . . C77 C -0.1214(6) 0.2363(4) 0.5128(6) 0.049(2) Uani 1 1 d . . . H77A H -0.2028 0.2348 0.5148 0.058 Uiso 1 1 calc R C . C78 C -0.0507(7) 0.1972(4) 0.5890(6) 0.051(2) Uani 1 1 d . C . H78 H -0.0832 0.1679 0.6432 0.062 Uiso 0.50 1 calc PR D 1 C79 C 0.0672(7) 0.2012(4) 0.5855(6) 0.0459(6) Uani 1 1 d . . . H79A H 0.1164 0.1755 0.6388 0.055 Uiso 1 1 calc R C . C80 C 0.1143(5) 0.2429(3) 0.5035(6) 0.0358(5) Uani 1 1 d . C . H80A H 0.1957 0.2442 0.5009 0.043 Uiso 1 1 calc R . . C81 C 0.1438(8) -0.0219(4) 0.2599(8) 0.041(2) Uani 0.50 1 d P C 1 H81A H 0.0819 -0.0459 0.2137 0.062 Uiso 0.50 1 calc PR C 1 H81B H 0.1428 -0.0364 0.3397 0.062 Uiso 0.50 1 calc PR C 1 H81C H 0.2183 -0.0341 0.2321 0.062 Uiso 0.50 1 calc PR C 1 C81' C -0.1135(12) 0.1534(7) 0.6734(12) 0.047(3) Uani 0.50 1 d P C 5 H81D H -0.1712 0.1824 0.7072 0.070 Uiso 0.50 1 calc PR C 5 H81E H -0.0578 0.1359 0.7338 0.070 Uiso 0.50 1 calc PR C 5 H81F H -0.1518 0.1137 0.6333 0.070 Uiso 0.50 1 calc PR C 5 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 N1 0.031(2) 0.049(4) 0.019(3) 0.008(3) -0.0007(19) -0.009(2) N2 0.0260(10) 0.0286(9) 0.0224(9) -0.001(2) 0.0014(7) 0.0005(19) C1 0.0265(11) 0.0343(11) 0.0189(9) -0.003(3) 0.0019(8) 0.002(2) C2 0.024(2) 0.035(3) 0.026(3) 0.006(3) -0.004(2) 0.003(2) C3 0.0241(11) 0.0325(11) 0.0262(10) -0.002(3) 0.0028(9) -0.002(2) C4 0.0225(11) 0.0408(12) 0.0248(11) 0.003(3) 0.0056(9) 0.001(2) C5 0.025(2) 0.026(3) 0.030(3) -0.004(3) 0.003(2) 0.002(2) C6 0.0250(11) 0.0250(10) 0.0238(10) -0.001(2) 0.0007(8) -0.001(2) C9 0.027(2) 0.032(3) 0.023(3) 0.003(3) 0.002(2) 0.000(2) C10 0.031(3) 0.027(3) 0.030(3) -0.001(3) 0.004(2) -0.005(2) C11 0.027(3) 0.047(4) 0.028(3) -0.004(3) 0.008(2) -0.004(3) C12 0.0253(12) 0.0474(13) 0.0227(10) -0.003(3) 0.0027(9) 0.002(2) O1 0.0371(9) 0.0312(9) 0.0228(7) 0.0001(17) 0.0002(7) -0.0014(16) C13 0.056(4) 0.036(4) 0.035(4) 0.009(3) 0.008(3) -0.003(3) O2 0.043(2) 0.046(3) 0.030(2) -0.004(2) 0.0003(18) -0.010(2) C14 0.089(3) 0.054(3) 0.0334(14) 0.000(3) -0.0140(15) 0.013(3) C15 0.0313(12) 0.0234(10) 0.0233(10) 0.001(2) -0.0002(9) 0.000(2) C16 0.035(3) 0.035(3) 0.022(3) 0.006(2) 0.008(2) 0.005(2) C17 0.039(3) 0.039(4) 0.053(4) 0.019(3) 0.021(3) 0.018(3) C18 0.033(3) 0.033(3) 0.035(3) 0.013(3) 0.010(2) 0.014(2) O3 0.0366(9) 0.0348(8) 0.0230(7) 0.0002(19) 0.0034(6) 0.0010(17) C19 0.049(3) 0.042(4) 0.023(3) 0.009(3) 0.016(3) 0.001(3) O4 0.031(3) 0.052(6) 0.027(4) 0.007(3) 0.008(3) 0.011(4) C20 0.038(5) 0.050(6) 0.048(6) 0.007(4) 0.008(4) 0.024(4) O4' 0.031(3) 0.052(6) 0.027(4) 0.007(3) 0.008(3) 0.011(4) C20' 0.038(5) 0.050(6) 0.048(6) 0.007(4) 0.008(4) 0.024(4) C7 0.019(6) 0.027(3) 0.020(4) 0.004(3) 0.006(6) 0.006(3) C21 0.024(6) 0.049(5) 0.035(7) 0.017(4) 0.004(4) 0.016(4) C22 0.026(5) 0.049(4) 0.045(4) 0.012(4) 0.004(5) 0.020(4) C23 0.047(8) 0.028(4) 0.033(5) 0.006(3) 0.014(6) 0.015(5) C24 0.028(6) 0.039(4) 0.037(5) -0.006(4) 0.004(5) 0.005(5) C25 0.026(6) 0.030(4) 0.025(4) -0.002(3) 0.000(5) 0.007(4) C7' 0.019(6) 0.027(3) 0.020(4) 0.004(3) 0.006(6) 0.006(3) C21' 0.024(6) 0.049(5) 0.035(7) 0.017(4) 0.004(4) 0.016(4) C22' 0.026(5) 0.049(4) 0.045(4) 0.012(4) 0.004(5) 0.020(4) C23' 0.047(8) 0.028(4) 0.033(5) 0.006(3) 0.014(6) 0.015(5) C24' 0.028(6) 0.039(4) 0.037(5) -0.006(4) 0.004(5) 0.005(5) C25' 0.026(6) 0.030(4) 0.025(4) -0.002(3) 0.000(5) 0.007(4) C8 0.0353(12) 0.0307(11) 0.0236(10) -0.001(3) 0.0063(9) 0.000(2) C26 0.0393(14) 0.0458(14) 0.0379(13) -0.007(3) 0.0110(11) -0.001(3) C27 0.050(4) 0.041(4) 0.054(4) 0.002(4) 0.026(3) 0.011(3) C28 0.067(4) 0.028(3) 0.042(4) -0.001(3) 0.032(3) -0.003(3) C29 0.074(2) 0.0326(12) 0.0325(13) 0.001(3) 0.0131(12) -0.001(4) C30 0.0453(14) 0.0323(12) 0.0307(11) 0.002(3) 0.0091(10) 0.003(3) C31 0.108(7) 0.065(6) 0.089(7) -0.016(5) 0.063(6) -0.011(5) N3 0.027(2) 0.034(3) 0.028(3) -0.004(2) 0.0016(19) -0.002(2) N4 0.0260(10) 0.0286(9) 0.0224(9) -0.001(2) 0.0014(7) 0.0005(19) C51 0.0265(11) 0.0343(11) 0.0189(9) -0.003(3) 0.0019(8) 0.002(2) C52 0.028(2) 0.024(3) 0.019(3) -0.001(2) 0.005(2) -0.002(2) C53 0.0241(11) 0.0325(11) 0.0262(10) -0.002(3) 0.0028(9) -0.002(2) C54 0.0225(11) 0.0408(12) 0.0248(11) 0.003(3) 0.0056(9) 0.001(2) C55 0.030(2) 0.022(3) 0.019(3) -0.002(2) 0.005(2) 0.005(2) C56 0.0250(11) 0.0250(10) 0.0238(10) -0.001(2) 0.0007(8) -0.001(2) C59 0.026(2) 0.036(4) 0.022(3) 0.000(3) 0.001(2) 0.002(2) C60 0.031(3) 0.048(4) 0.024(3) -0.001(3) 0.004(2) 0.008(3) C61 0.026(2) 0.039(4) 0.030(3) 0.007(3) 0.003(2) 0.007(3) C62 0.0253(12) 0.0474(13) 0.0227(10) -0.003(3) 0.0027(9) 0.002(2) O5 0.0371(9) 0.0312(9) 0.0228(7) 0.0001(17) 0.0002(7) -0.0014(16) C63 0.065(4) 0.038(4) 0.026(3) -0.007(3) -0.008(3) 0.018(3) O6 0.046(2) 0.054(3) 0.025(2) 0.005(2) 0.0017(18) 0.023(2) C64 0.089(3) 0.054(3) 0.0334(14) 0.000(3) -0.0140(15) 0.013(3) C65 0.0313(12) 0.0234(10) 0.0233(10) 0.001(2) -0.0002(9) 0.000(2) C66 0.033(3) 0.025(3) 0.032(3) -0.001(2) 0.009(2) -0.001(2) C67 0.030(3) 0.034(3) 0.040(4) -0.003(3) 0.012(2) -0.004(2) C68 0.036(3) 0.031(3) 0.031(3) -0.004(3) 0.003(2) 0.002(2) O7 0.0366(9) 0.0348(8) 0.0230(7) 0.0002(19) 0.0034(6) 0.0010(17) C69 0.056(4) 0.044(4) 0.029(4) -0.005(3) 0.005(3) -0.003(3) O8 0.034(3) 0.031(5) 0.055(4) -0.011(4) 0.016(3) -0.010(3) C70 0.047(6) 0.077(10) 0.079(8) -0.049(7) 0.030(5) -0.029(6) O8' 0.034(3) 0.031(5) 0.055(4) -0.011(4) 0.016(3) -0.010(3) C70' 0.047(6) 0.077(10) 0.079(8) -0.049(7) 0.030(5) -0.029(6) C57 0.038(3) 0.036(4) 0.024(3) -0.005(3) 0.012(3) -0.008(3) C71 0.052(6) 0.020(7) 0.033(5) 0.002(10) 0.009(6) 0.000(6) C72 0.048(4) 0.024(3) 0.051(4) -0.001(3) 0.015(3) -0.004(3) C73 0.040(8) 0.032(4) 0.028(6) -0.006(4) 0.003(5) -0.012(6) C74 0.059(9) 0.025(5) 0.021(8) -0.014(4) 0.005(5) -0.008(5) C75 0.048(4) 0.024(3) 0.051(4) -0.001(3) 0.015(3) -0.004(3) C57' 0.038(3) 0.036(4) 0.024(3) -0.005(3) 0.012(3) -0.008(3) C71' 0.052(6) 0.020(7) 0.033(5) 0.002(10) 0.009(6) 0.000(6) C72' 0.048(4) 0.024(3) 0.051(4) -0.001(3) 0.015(3) -0.004(3) C73' 0.040(8) 0.032(4) 0.028(6) -0.006(4) 0.003(5) -0.012(6) C74' 0.059(9) 0.025(5) 0.021(8) -0.014(4) 0.005(5) -0.008(5) C75' 0.048(4) 0.024(3) 0.051(4) -0.001(3) 0.015(3) -0.004(3) C58 0.0353(12) 0.0307(11) 0.0236(10) -0.001(3) 0.0063(9) 0.000(2) C76 0.0393(14) 0.0458(14) 0.0379(13) -0.007(3) 0.0110(11) -0.001(3) C77 0.046(3) 0.066(5) 0.036(4) -0.013(4) 0.020(3) -0.014(4) C78 0.081(5) 0.038(4) 0.039(4) -0.015(3) 0.027(4) -0.023(4) C79 0.074(2) 0.0326(12) 0.0325(13) 0.001(3) 0.0131(12) -0.001(4) C80 0.0453(14) 0.0323(12) 0.0307(11) 0.002(3) 0.0091(10) 0.003(3) C81 0.046(5) 0.020(4) 0.056(6) 0.004(4) -0.008(4) -0.008(4) C81' 0.075(9) 0.024(6) 0.047(7) -0.004(6) 0.043(7) -0.001(6) _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 N1 C4 1.391(9) . ? N1 C1 1.476(7) . ? N1 H1 0.84(6) . ? N2 C5 1.426(7) . ? N2 C2 1.501(7) . ? N2 H2 0.90(6) . ? C1 C6 1.501(7) . ? C1 C7 1.534(10) . ? C1 C7' 1.539(17) . ? C1 C2 1.616(8) . ? C2 C8 1.510(8) . ? C2 C3 1.520(9) . ? C3 C4 1.378(8) . ? C3 C9 1.381(8) . ? C4 C12 1.401(9) . ? C5 C6 1.366(8) . ? C5 C18 1.398(7) . ? C6 C15 1.399(8) . ? C9 O1 1.373(7) . ? C9 C10 1.390(8) . ? C10 C11 1.390(8) . ? C10 H10 0.9500 . ? C11 O2 1.364(8) . ? C11 C12 1.391(9) . ? C12 H12 0.9500 . ? O1 C13 1.433(8) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? O2 C14 1.410(7) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 O3 1.355(7) . ? C15 C16 1.366(7) . ? C16 C17 1.404(9) . ? C16 H16 0.9500 . ? C17 C18 1.369(9) . ? C17 O4 1.414(9) . ? C17 O4' 1.421(9) . ? C18 H18 0.9500 . ? O3 C19 1.419(7) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? O4 C20 1.429(11) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? O4' C20' 1.443(11) . ? C20' H20D 0.9800 . ? C20' H20E 0.9800 . ? C20' H20F 0.9800 . ? C7 C21 1.378(10) . ? C7 C25 1.395(10) . ? C21 C22 1.386(12) . ? C21 H21 0.9500 . ? C22 C23 1.396(12) . ? C22 H22 0.9500 . ? C23 C24 1.376(10) . ? C23 H23 0.9500 . ? C24 C25 1.355(11) . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? C7' C21' 1.365(18) . ? C7' C25' 1.395(17) . ? C21' C22' 1.389(19) . ? C21' H21' 0.9500 . ? C22' C23' 1.388(19) . ? C22' H22' 0.9500 . ? C23' C24' 1.360(19) . ? C23' H23' 0.9500 . ? C24' C25' 1.362(18) . ? C24' H24' 0.9500 . ? C25' H25' 0.9500 . ? C8 C26 1.379(8) . ? C8 C30 1.400(8) . ? C26 C27 1.407(9) . ? C26 H26 0.9500 . ? C27 C28 1.361(10) . ? C27 H27 0.9500 . ? C28 C29 1.386(9) . ? C28 C31 1.518(10) . ? C29 C30 1.387(9) . ? C29 H29 0.9500 . ? C30 H30 0.9500 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? N3 C54 1.400(8) . ? N3 C51 1.486(7) . ? N3 H3 0.97(5) . ? N4 C55 1.378(7) . ? N4 C52 1.477(7) . ? N4 H4 0.97(6) . ? C51 C57 1.504(10) . ? C51 C56 1.510(8) . ? C51 C52 1.619(8) . ? C52 C53 1.486(8) . ? C52 C58 1.519(8) . ? C53 C54 1.388(8) . ? C53 C59 1.391(9) . ? C54 C62 1.385(9) . ? C55 C68 1.378(8) . ? C55 C56 1.400(7) . ? C56 C65 1.390(8) . ? C59 O5 1.363(6) . ? C59 C60 1.377(9) . ? C60 C61 1.413(8) . ? C60 H60 0.9500 . ? C61 C62 1.372(9) . ? C61 O6 1.383(7) . ? C62 H62 0.9500 . ? O5 C63 1.410(8) . ? C63 H63A 0.9800 . ? C63 H63B 0.9800 . ? C63 H63C 0.9800 . ? O6 C64 1.457(7) . ? C64 H64A 0.9800 . ? C64 H64B 0.9800 . ? C64 H64C 0.9800 . ? C65 O7 1.379(7) . ? C65 C66 1.386(7) . ? C66 C67 1.372(9) . ? C66 H66A 0.9500 . ? C67 O8' 1.392(11) . ? C67 O8 1.394(7) . ? C67 C68 1.398(9) . ? C68 H68A 0.9500 . ? O7 C69 1.444(7) . ? C69 H69A 0.9800 . ? C69 H69B 0.9800 . ? C69 H69C 0.9800 . ? O8 C70 1.425(10) . ? C70 H70A 0.9800 . ? C70 H70B 0.9800 . ? C70 H70C 0.9800 . ? O8' C70' 1.422(13) . ? C70' H70D 0.9800 . ? C70' H70E 0.9800 . ? C70' H70F 0.9800 . ? C57 C75 1.380(14) . ? C57 C71 1.406(13) . ? C71 C72 1.403(15) . ? C71 H71 0.9500 . ? C72 C73 1.354(15) . ? C72 H72 0.9500 . ? C73 C74 1.378(14) . ? C73 C81 1.541(16) . ? C74 C75 1.416(14) . ? C74 H74 0.9500 . ? C75 H75 0.9500 . ? C71' C72' 1.403(15) . ? C71' H71' 0.9500 . ? C72' C73' 1.354(16) . ? C72' H72' 0.9500 . ? C73' C74' 1.391(15) . ? C73' H73' 0.9500 . ? C74' C75' 1.416(14) . ? C74' H74' 0.9500 . ? C75' H75' 0.9500 . ? C58 C80 1.378(8) . ? C58 C76 1.393(8) . ? C76 C77 1.367(10) . ? C76 H76A 0.9500 . ? C77 C78 1.384(11) . ? C77 H77A 0.9500 . ? C78 C79 1.379(10) . ? C78 C81' 1.530(14) . ? C78 H78 0.9500 . ? C79 C80 1.397(9) . ? C79 H79A 0.9500 . ? C80 H80A 0.9500 . ? C81 H81A 0.9800 . ? C81 H81B 0.9800 . ? C81 H81C 0.9800 . ? C81' H81D 0.9800 . ? C81' H81E 0.9800 . ? C81' H81F 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 C4 N1 C1 109.0(5) . . ? C4 N1 H1 127(4) . . ? C1 N1 H1 113(4) . . ? C5 N2 C2 107.2(5) . . ? C5 N2 H2 106(3) . . ? C2 N2 H2 115(3) . . ? N1 C1 C6 113.2(5) . . ? N1 C1 C7 109.5(7) . . ? C6 C1 C7 114.2(8) . . ? N1 C1 C7' 119.1(17) . . ? C6 C1 C7' 104.8(19) . . ? N1 C1 C2 103.1(5) . . ? C6 C1 C2 101.3(4) . . ? C7 C1 C2 115.0(11) . . ? C7' C1 C2 114(3) . . ? N2 C2 C8 110.9(5) . . ? N2 C2 C3 110.7(5) . . ? C8 C2 C3 114.1(5) . . ? N2 C2 C1 103.8(4) . . ? C8 C2 C1 116.0(5) . . ? C3 C2 C1 100.5(5) . . ? C4 C3 C9 120.3(6) . . ? C4 C3 C2 110.5(5) . . ? C9 C3 C2 129.2(5) . . ? C3 C4 N1 111.4(5) . . ? C3 C4 C12 121.7(6) . . ? N1 C4 C12 126.9(6) . . ? C6 C5 C18 123.3(6) . . ? C6 C5 N2 111.7(5) . . ? C18 C5 N2 125.0(6) . . ? C5 C6 C15 119.2(5) . . ? C5 C6 C1 111.8(5) . . ? C15 C6 C1 128.9(5) . . ? O1 C9 C3 114.3(5) . . ? O1 C9 C10 126.1(6) . . ? C3 C9 C10 119.6(6) . . ? C11 C10 C9 119.4(6) . . ? C11 C10 H10 120.3 . . ? C9 C10 H10 120.3 . . ? O2 C11 C10 113.6(6) . . ? O2 C11 C12 124.2(6) . . ? C10 C11 C12 122.2(6) . . ? C11 C12 C4 116.8(6) . . ? C11 C12 H12 121.6 . . ? C4 C12 H12 121.6 . . ? C9 O1 C13 116.8(5) . . ? O1 C13 H13A 109.5 . . ? O1 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O1 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C11 O2 C14 118.6(6) . . ? O2 C14 H14A 109.5 . . ? O2 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? O2 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O3 C15 C16 124.4(5) . . ? O3 C15 C6 115.6(5) . . ? C16 C15 C6 120.0(5) . . ? C15 C16 C17 118.1(5) . . ? C15 C16 H16 121.0 . . ? C17 C16 H16 121.0 . . ? C18 C17 C16 124.2(5) . . ? C18 C17 O4 124.6(7) . . ? C16 C17 O4 109.1(7) . . ? C18 C17 O4' 120.1(7) . . ? C16 C17 O4' 114.6(7) . . ? C17 C18 C5 115.0(6) . . ? C17 C18 H18 122.5 . . ? C5 C18 H18 122.5 . . ? C15 O3 C19 116.2(4) . . ? O3 C19 H19A 109.5 . . ? O3 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? O3 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C17 O4 C20 115.1(8) . . ? C17 O4' C20' 119.9(9) . . ? C21 C7 C25 119.2(8) . . ? C21 C7 C1 123.1(10) . . ? C25 C7 C1 117.6(9) . . ? C7 C21 C22 119.4(9) . . ? C7 C21 H21 120.3 . . ? C22 C21 H21 120.3 . . ? C21 C22 C23 121.3(8) . . ? C21 C22 H22 119.4 . . ? C23 C22 H22 119.4 . . ? C24 C23 C22 117.6(8) . . ? C24 C23 H23 121.2 . . ? C22 C23 H23 121.2 . . ? C25 C24 C23 121.9(9) . . ? C25 C24 H24 119.0 . . ? C23 C24 H24 119.0 . . ? C24 C25 C7 120.5(8) . . ? C24 C25 H25 119.8 . . ? C7 C25 H25 119.8 . . ? C21' C7' C25' 120.1(18) . . ? C21' C7' C1 115(3) . . ? C25' C7' C1 124(3) . . ? C7' C21' C22' 119(2) . . ? C7' C21' H21' 120.6 . . ? C22' C21' H21' 120.6 . . ? C23' C22' C21' 121(2) . . ? C23' C22' H22' 119.7 . . ? C21' C22' H22' 119.7 . . ? C24' C23' C22' 119(2) . . ? C24' C23' H23' 120.7 . . ? C22' C23' H23' 120.7 . . ? C23' C24' C25' 122(2) . . ? C23' C24' H24' 119.2 . . ? C25' C24' H24' 119.2 . . ? C24' C25' C7' 119.4(19) . . ? C24' C25' H25' 120.3 . . ? C7' C25' H25' 120.3 . . ? C26 C8 C30 119.7(6) . . ? C26 C8 C2 119.4(5) . . ? C30 C8 C2 120.9(5) . . ? C8 C26 C27 118.5(6) . . ? C8 C26 H26 120.7 . . ? C27 C26 H26 120.7 . . ? C28 C27 C26 123.4(6) . . ? C28 C27 H27 118.3 . . ? C26 C27 H27 118.3 . . ? C27 C28 C29 116.8(6) . . ? C27 C28 C31 120.4(7) . . ? C29 C28 C31 122.9(7) . . ? C28 C29 C30 122.4(7) . . ? C28 C29 H29 118.8 . . ? C30 C29 H29 118.8 . . ? C29 C30 C8 119.2(6) . . ? C29 C30 H30 120.4 . . ? C8 C30 H30 120.4 . . ? C28 C31 H31A 109.5 . . ? C28 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C28 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C54 N3 C51 107.9(5) . . ? C54 N3 H3 110(3) . . ? C51 N3 H3 115(3) . . ? C55 N4 C52 109.6(5) . . ? C55 N4 H4 120(3) . . ? C52 N4 H4 111(3) . . ? N3 C51 C57 112.4(5) . . ? N3 C51 C56 113.5(5) . . ? C57 C51 C56 111.1(5) . . ? N3 C51 C52 103.7(4) . . ? C57 C51 C52 115.5(5) . . ? C56 C51 C52 99.9(4) . . ? N4 C52 C53 113.5(5) . . ? N4 C52 C58 111.2(5) . . ? C53 C52 C58 114.0(4) . . ? N4 C52 C51 103.6(4) . . ? C53 C52 C51 100.4(5) . . ? C58 C52 C51 113.3(5) . . ? C54 C53 C59 119.3(6) . . ? C54 C53 C52 112.2(5) . . ? C59 C53 C52 128.4(5) . . ? C62 C54 C53 122.1(6) . . ? C62 C54 N3 127.4(6) . . ? C53 C54 N3 110.4(5) . . ? C68 C55 N4 127.6(5) . . ? C68 C55 C56 121.8(5) . . ? N4 C55 C56 110.3(5) . . ? C65 C56 C55 119.5(5) . . ? C65 C56 C51 128.9(5) . . ? C55 C56 C51 111.4(5) . . ? O5 C59 C60 123.6(6) . . ? O5 C59 C53 116.0(5) . . ? C60 C59 C53 120.4(6) . . ? C59 C60 C61 118.5(6) . . ? C59 C60 H60 120.8 . . ? C61 C60 H60 120.8 . . ? C62 C61 O6 124.2(5) . . ? C62 C61 C60 122.4(6) . . ? O6 C61 C60 113.4(6) . . ? C61 C62 C54 117.4(6) . . ? C61 C62 H62 121.3 . . ? C54 C62 H62 121.3 . . ? C59 O5 C63 117.9(5) . . ? O5 C63 H63A 109.5 . . ? O5 C63 H63B 109.5 . . ? H63A C63 H63B 109.5 . . ? O5 C63 H63C 109.5 . . ? H63A C63 H63C 109.5 . . ? H63B C63 H63C 109.5 . . ? C61 O6 C64 115.0(5) . . ? O6 C64 H64A 109.5 . . ? O6 C64 H64B 109.5 . . ? H64A C64 H64B 109.5 . . ? O6 C64 H64C 109.5 . . ? H64A C64 H64C 109.5 . . ? H64B C64 H64C 109.5 . . ? O7 C65 C66 125.0(5) . . ? O7 C65 C56 115.7(5) . . ? C66 C65 C56 119.3(5) . . ? C67 C66 C65 120.1(5) . . ? C67 C66 H66A 119.9 . . ? C65 C66 H66A 119.9 . . ? C66 C67 O8' 113.1(13) . . ? C66 C67 O8 115.1(6) . . ? C66 C67 C68 122.0(5) . . ? O8' C67 C68 123.8(13) . . ? O8 C67 C68 122.2(7) . . ? C55 C68 C67 117.2(6) . . ? C55 C68 H68A 121.4 . . ? C67 C68 H68A 121.4 . . ? C65 O7 C69 117.0(4) . . ? O7 C69 H69A 109.5 . . ? O7 C69 H69B 109.5 . . ? H69A C69 H69B 109.5 . . ? O7 C69 H69C 109.5 . . ? H69A C69 H69C 109.5 . . ? H69B C69 H69C 109.5 . . ? C67 O8 C70 117.4(8) . . ? C67 O8' C70' 115(2) . . ? C75 C57 C71 113.6(10) . . ? C75 C57 C51 115.8(8) . . ? C71 C57 C51 130.6(8) . . ? C72 C71 C57 122.9(13) . . ? C72 C71 H71 118.5 . . ? C57 C71 H71 118.5 . . ? C73 C72 C71 120.5(13) . . ? C73 C72 H72 119.7 . . ? C71 C72 H72 119.7 . . ? C72 C73 C74 119.8(13) . . ? C72 C73 C81 121.1(11) . . ? C74 C73 C81 119.1(12) . . ? C73 C74 C75 118.1(14) . . ? C73 C74 H74 121.0 . . ? C75 C74 H74 121.0 . . ? C57 C75 C74 124.8(13) . . ? C57 C75 H75 117.6 . . ? C74 C75 H75 117.6 . . ? C72' C71' H71' 119.9 . . ? C73' C72' C71' 119.3(13) . . ? C73' C72' H72' 120.4 . . ? C71' C72' H72' 120.4 . . ? C72' C73' C74' 121.2(12) . . ? C72' C73' H73' 119.4 . . ? C74' C73' H73' 119.4 . . ? C73' C74' C75' 119.4(14) . . ? C73' C74' H74' 120.3 . . ? C75' C74' H74' 120.3 . . ? C74' C75' H75' 120.2 . . ? C80 C58 C76 115.8(6) . . ? C80 C58 C52 122.8(5) . . ? C76 C58 C52 121.3(6) . . ? C77 C76 C58 123.9(7) . . ? C77 C76 H76A 118.1 . . ? C58 C76 H76A 118.1 . . ? C76 C77 C78 119.0(6) . . ? C76 C77 H77A 120.5 . . ? C78 C77 H77A 120.5 . . ? C79 C78 C77 119.4(7) . . ? C79 C78 C81' 125.4(10) . . ? C77 C78 C81' 115.2(9) . . ? C79 C78 H78 120.3 . . ? C77 C78 H78 120.3 . . ? C78 C79 C80 120.0(7) . . ? C78 C79 H79A 120.0 . . ? C80 C79 H79A 120.0 . . ? C58 C80 C79 121.9(6) . . ? C58 C80 H80A 119.1 . . ? C79 C80 H80A 119.1 . . ? C78 C81' H81D 109.5 . . ? C78 C81' H81E 109.5 . . ? C78 C81' H81F 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 C4 N1 C1 C6 84.9(6) . . . . ? C4 N1 C1 C7 -146.5(11) . . . . ? C4 N1 C1 C7' -151(3) . . . . ? C4 N1 C1 C2 -23.6(6) . . . . ? C5 N2 C2 C8 -146.0(5) . . . . ? C5 N2 C2 C3 86.2(6) . . . . ? C5 N2 C2 C1 -20.8(6) . . . . ? N1 C1 C2 N2 135.2(5) . . . . ? C6 C1 C2 N2 17.9(6) . . . . ? C7 C1 C2 N2 -105.8(7) . . . . ? C7' C1 C2 N2 -94.1(16) . . . . ? N1 C1 C2 C8 -102.9(5) . . . . ? C6 C1 C2 C8 139.8(5) . . . . ? C7 C1 C2 C8 16.2(8) . . . . ? C7' C1 C2 C8 27.8(16) . . . . ? N1 C1 C2 C3 20.6(5) . . . . ? C6 C1 C2 C3 -96.7(5) . . . . ? C7 C1 C2 C3 139.7(6) . . . . ? C7' C1 C2 C3 151.3(16) . . . . ? N2 C2 C3 C4 -120.9(5) . . . . ? C8 C2 C3 C4 113.1(6) . . . . ? C1 C2 C3 C4 -11.7(6) . . . . ? N2 C2 C3 C9 59.4(8) . . . . ? C8 C2 C3 C9 -66.6(8) . . . . ? C1 C2 C3 C9 168.6(6) . . . . ? C9 C3 C4 N1 177.2(5) . . . . ? C2 C3 C4 N1 -2.4(7) . . . . ? C9 C3 C4 C12 -2.8(9) . . . . ? C2 C3 C4 C12 177.6(5) . . . . ? C1 N1 C4 C3 17.5(7) . . . . ? C1 N1 C4 C12 -162.6(5) . . . . ? C2 N2 C5 C6 16.2(7) . . . . ? C2 N2 C5 C18 -166.5(6) . . . . ? C18 C5 C6 C15 -4.7(9) . . . . ? N2 C5 C6 C15 172.7(5) . . . . ? C18 C5 C6 C1 179.0(6) . . . . ? N2 C5 C6 C1 -3.7(7) . . . . ? N1 C1 C6 C5 -119.0(6) . . . . ? C7 C1 C6 C5 114.9(11) . . . . ? C7' C1 C6 C5 110(3) . . . . ? C2 C1 C6 C5 -9.3(6) . . . . ? N1 C1 C6 C15 65.1(8) . . . . ? C7 C1 C6 C15 -61.0(12) . . . . ? C7' C1 C6 C15 -66(3) . . . . ? C2 C1 C6 C15 174.8(6) . . . . ? C4 C3 C9 O1 -179.1(5) . . . . ? C2 C3 C9 O1 0.5(9) . . . . ? C4 C3 C9 C10 1.6(9) . . . . ? C2 C3 C9 C10 -178.8(5) . . . . ? O1 C9 C10 C11 -178.7(5) . . . . ? C3 C9 C10 C11 0.5(9) . . . . ? C9 C10 C11 O2 179.3(5) . . . . ? C9 C10 C11 C12 -1.6(9) . . . . ? O2 C11 C12 C4 179.6(5) . . . . ? C10 C11 C12 C4 0.5(8) . . . . ? C3 C4 C12 C11 1.6(8) . . . . ? N1 C4 C12 C11 -178.3(5) . . . . ? C3 C9 O1 C13 179.8(5) . . . . ? C10 C9 O1 C13 -1.0(8) . . . . ? C10 C11 O2 C14 -163.8(5) . . . . ? C12 C11 O2 C14 17.0(9) . . . . ? C5 C6 C15 O3 -177.5(5) . . . . ? C1 C6 C15 O3 -1.8(9) . . . . ? C5 C6 C15 C16 4.9(9) . . . . ? C1 C6 C15 C16 -179.5(6) . . . . ? O3 C15 C16 C17 179.6(6) . . . . ? C6 C15 C16 C17 -3.0(9) . . . . ? C15 C16 C17 C18 0.9(11) . . . . ? C15 C16 C17 O4 165.2(7) . . . . ? C15 C16 C17 O4' -167.4(8) . . . . ? C16 C17 C18 C5 -0.5(11) . . . . ? O4 C17 C18 C5 -162.4(8) . . . . ? O4' C17 C18 C5 167.1(8) . . . . ? C6 C5 C18 C17 2.5(10) . . . . ? N2 C5 C18 C17 -174.6(6) . . . . ? C16 C15 O3 C19 -8.5(9) . . . . ? C6 C15 O3 C19 174.0(5) . . . . ? C18 C17 O4 C20 -6.9(14) . . . . ? C16 C17 O4 C20 -171.1(9) . . . . ? C18 C17 O4' C20' 0.8(15) . . . . ? C16 C17 O4' C20' 169.5(10) . . . . ? N1 C1 C7 C21 12(3) . . . . ? C6 C1 C7 C21 140(2) . . . . ? C2 C1 C7 C21 -103(2) . . . . ? N1 C1 C7 C25 -165.2(17) . . . . ? C6 C1 C7 C25 -37(2) . . . . ? C2 C1 C7 C25 79(2) . . . . ? C25 C7 C21 C22 -3(4) . . . . ? C1 C7 C21 C22 -179.7(18) . . . . ? C7 C21 C22 C23 5(3) . . . . ? C21 C22 C23 C24 -5(3) . . . . ? C22 C23 C24 C25 2(3) . . . . ? C23 C24 C25 C7 0(3) . . . . ? C21 C7 C25 C24 0(4) . . . . ? C1 C7 C25 C24 177.3(18) . . . . ? N1 C1 C7' C21' 21(7) . . . . ? C6 C1 C7' C21' 148(6) . . . . ? C2 C1 C7' C21' -102(6) . . . . ? N1 C1 C7' C25' -164(5) . . . . ? C6 C1 C7' C25' -36(7) . . . . ? C2 C1 C7' C25' 73(7) . . . . ? C25' C7' C21' C22' 10(11) . . . . ? C1 C7' C21' C22' -175(5) . . . . ? C7' C21' C22' C23' -11(10) . . . . ? C21' C22' C23' C24' 5(9) . . . . ? C22' C23' C24' C25' 2(9) . . . . ? C23' C24' C25' C7' -3(10) . . . . ? C21' C7' C25' C24' -3(11) . . . . ? C1 C7' C25' C24' -178(5) . . . . ? N2 C2 C8 C26 -155.0(6) . . . . ? C3 C2 C8 C26 -29.2(8) . . . . ? C1 C2 C8 C26 86.9(7) . . . . ? N2 C2 C8 C30 27.0(8) . . . . ? C3 C2 C8 C30 152.9(6) . . . . ? C1 C2 C8 C30 -91.0(7) . . . . ? C30 C8 C26 C27 0.3(10) . . . . ? C2 C8 C26 C27 -177.6(6) . . . . ? C8 C26 C27 C28 0.4(11) . . . . ? C26 C27 C28 C29 -0.2(11) . . . . ? C26 C27 C28 C31 179.5(7) . . . . ? C27 C28 C29 C30 -0.8(10) . . . . ? C31 C28 C29 C30 179.5(7) . . . . ? C28 C29 C30 C8 1.5(10) . . . . ? C26 C8 C30 C29 -1.3(10) . . . . ? C2 C8 C30 C29 176.7(6) . . . . ? C54 N3 C51 C57 149.1(5) . . . . ? C54 N3 C51 C56 -83.7(6) . . . . ? C54 N3 C51 C52 23.7(6) . . . . ? C55 N4 C52 C53 -84.8(6) . . . . ? C55 N4 C52 C58 145.2(5) . . . . ? C55 N4 C52 C51 23.1(6) . . . . ? N3 C51 C52 N4 -136.6(5) . . . . ? C57 C51 C52 N4 100.0(6) . . . . ? C56 C51 C52 N4 -19.2(6) . . . . ? N3 C51 C52 C53 -19.2(5) . . . . ? C57 C51 C52 C53 -142.6(5) . . . . ? C56 C51 C52 C53 98.2(5) . . . . ? N3 C51 C52 C58 102.8(5) . . . . ? C57 C51 C52 C58 -20.7(7) . . . . ? C56 C51 C52 C58 -139.9(5) . . . . ? N4 C52 C53 C54 118.8(5) . . . . ? C58 C52 C53 C54 -112.5(6) . . . . ? C51 C52 C53 C54 8.9(6) . . . . ? N4 C52 C53 C59 -58.4(8) . . . . ? C58 C52 C53 C59 70.3(8) . . . . ? C51 C52 C53 C59 -168.3(6) . . . . ? C59 C53 C54 C62 -0.2(8) . . . . ? C52 C53 C54 C62 -177.7(5) . . . . ? C59 C53 C54 N3 -176.8(5) . . . . ? C52 C53 C54 N3 5.7(6) . . . . ? C51 N3 C54 C62 164.3(5) . . . . ? C51 N3 C54 C53 -19.3(6) . . . . ? C52 N4 C55 C68 168.5(6) . . . . ? C52 N4 C55 C56 -17.6(7) . . . . ? C68 C55 C56 C65 1.7(9) . . . . ? N4 C55 C56 C65 -172.7(5) . . . . ? C68 C55 C56 C51 177.9(6) . . . . ? N4 C55 C56 C51 3.5(7) . . . . ? N3 C51 C56 C65 -64.2(8) . . . . ? C57 C51 C56 C65 63.6(8) . . . . ? C52 C51 C56 C65 -174.0(6) . . . . ? N3 C51 C56 C55 120.0(5) . . . . ? C57 C51 C56 C55 -112.1(6) . . . . ? C52 C51 C56 C55 10.2(6) . . . . ? C54 C53 C59 O5 -177.5(5) . . . . ? C52 C53 C59 O5 -0.5(9) . . . . ? C54 C53 C59 C60 0.2(9) . . . . ? C52 C53 C59 C60 177.2(5) . . . . ? O5 C59 C60 C61 177.0(5) . . . . ? C53 C59 C60 C61 -0.5(9) . . . . ? C59 C60 C61 C62 0.8(9) . . . . ? C59 C60 C61 O6 -178.6(5) . . . . ? O6 C61 C62 C54 178.5(5) . . . . ? C60 C61 C62 C54 -0.9(9) . . . . ? C53 C54 C62 C61 0.6(8) . . . . ? N3 C54 C62 C61 176.5(5) . . . . ? C60 C59 O5 C63 3.4(8) . . . . ? C53 C59 O5 C63 -179.0(6) . . . . ? C62 C61 O6 C64 0.2(8) . . . . ? C60 C61 O6 C64 179.6(5) . . . . ? C55 C56 C65 O7 176.2(5) . . . . ? C51 C56 C65 O7 0.7(9) . . . . ? C55 C56 C65 C66 -1.7(9) . . . . ? C51 C56 C65 C66 -177.1(6) . . . . ? O7 C65 C66 C67 -178.3(6) . . . . ? C56 C65 C66 C67 -0.7(9) . . . . ? C65 C66 C67 O8' -165.1(14) . . . . ? C65 C66 C67 O8 173.8(7) . . . . ? C65 C66 C67 C68 3.2(10) . . . . ? N4 C55 C68 C67 174.0(6) . . . . ? C56 C55 C68 C67 0.7(9) . . . . ? C66 C67 C68 C55 -3.1(10) . . . . ? O8' C67 C68 C55 163.8(16) . . . . ? O8 C67 C68 C55 -173.1(8) . . . . ? C66 C65 O7 C69 3.0(8) . . . . ? C56 C65 O7 C69 -174.7(5) . . . . ? C66 C67 O8 C70 -170.6(9) . . . . ? C68 C67 O8 C70 0.1(12) . . . . ? C66 C67 O8' C70' 169(2) . . . . ? C68 C67 O8' C70' 1(3) . . . . ? N3 C51 C57 C75 167(2) . . . . ? C56 C51 C57 C75 39(2) . . . . ? C52 C51 C57 C75 -74(2) . . . . ? N3 C51 C57 C71 -12(3) . . . . ? C56 C51 C57 C71 -140(3) . . . . ? C52 C51 C57 C71 107(3) . . . . ? C75 C57 C71 C72 2(6) . . . . ? C51 C57 C71 C72 -179(2) . . . . ? C57 C71 C72 C73 -3(6) . . . . ? C71 C72 C73 C74 5(4) . . . . ? C71 C72 C73 C81 -175(3) . . . . ? C72 C73 C74 C75 -5(3) . . . . ? C81 C73 C74 C75 175(2) . . . . ? C71 C57 C75 C74 -2(5) . . . . ? C51 C57 C75 C74 178(3) . . . . ? C73 C74 C75 C57 4(5) . . . . ? C71' C72' C73' C74' -2(4) . . . . ? C72' C73' C74' C75' 4(3) . . . . ? N4 C52 C58 C80 -24.4(8) . . . . ? C53 C52 C58 C80 -154.2(6) . . . . ? C51 C52 C58 C80 91.8(7) . . . . ? N4 C52 C58 C76 158.7(6) . . . . ? C53 C52 C58 C76 28.9(8) . . . . ? C51 C52 C58 C76 -85.1(7) . . . . ? C80 C58 C76 C77 -0.1(10) . . . . ? C52 C58 C76 C77 177.0(6) . . . . ? C58 C76 C77 C78 -0.2(11) . . . . ? C76 C77 C78 C79 1.0(11) . . . . ? C76 C77 C78 C81' 179.8(8) . . . . ? C77 C78 C79 C80 -1.7(10) . . . . ? C81' C78 C79 C80 179.6(8) . . . . ? C76 C58 C80 C79 -0.6(9) . . . . ? C52 C58 C80 C79 -177.6(6) . . . . ? C78 C79 C80 C58 1.5(10) . . . . ? 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 O3 0.84(6) 2.70(6) 3.177(6) 117(4) . N1 H1 O8 0.84(6) 2.91(6) 3.542(12) 133(5) 2_645 N1 H1 O8' 0.84(6) 2.54(6) 3.22(3) 138(5) 2_645 N2 H2 O1 0.90(6) 2.52(6) 3.056(6) 119(4) . N3 H3 O7 0.97(5) 2.65(5) 3.190(6) 115(4) . N3 H3 O4 0.97(5) 2.12(5) 3.043(10) 158(5) 2_655 N3 H3 O4' 0.97(5) 2.63(5) 3.502(11) 149(4) 2_655 N4 H4 O5 0.97(6) 2.45(5) 3.078(6) 122(4) . _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.346 _refine_diff_density_min -0.362 _refine_diff_density_rms 0.048 #===end _database_code_depnum_ccdc_archive 'CCDC 937924'