# Electronic Supplementary Material (ESI) for Dalton Transactions # 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_ybdo3aae #TrackingRef 'ybdo3aae.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H28 N5 O6 Yb, 5(H2 O)' _chemical_formula_sum 'C16 H38 N5 O11 Yb' _chemical_formula_weight 649.55 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' Yb Yb -0.3850 5.5486 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' 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 16.8708(7) _cell_length_b 7.5238(4) _cell_length_c 18.4880(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.4230(10) _cell_angle_gamma 90.00 _cell_volume 2346.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9558 _cell_measurement_theta_min 2.2032 _cell_measurement_theta_max 27.4980 _exptl_crystal_description irregular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.51 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.839 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1308 _exptl_absorpt_coefficient_mu 4.051 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.2323 _exptl_absorpt_correction_T_max 0.6828 _exptl_absorpt_process_details 'SADABS V2012/1 (Bruker AXS Inc.)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 43484 _diffrn_reflns_av_R_equivalents 0.0204 _diffrn_reflns_av_sigmaI/netI 0.0113 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.21 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5374 _reflns_number_gt 5160 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Instrument Service v2012.12.0.0' _computing_cell_refinement 'SAINT V8.27B (Bruker AXS Inc., 2012)' _computing_data_reduction 'SAINT V8.27B (Bruker AXS Inc., 2012)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0086P)^2^+2.5862P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5374 _refine_ls_number_parameters 347 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0147 _refine_ls_R_factor_gt 0.0137 _refine_ls_wR_factor_ref 0.0306 _refine_ls_wR_factor_gt 0.0303 _refine_ls_goodness_of_fit_ref 1.129 _refine_ls_restrained_S_all 1.129 _refine_ls_shift/su_max 0.002 _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 Yb1 Yb 0.262225(4) 0.145972(9) 0.456366(4) 0.00875(2) Uani 1 1 d . . . N1A N 0.27388(13) 0.3678(3) 0.35492(11) 0.0128(4) Uani 0.851(3) 1 d P A 1 C2A C 0.20501(15) 0.3528(3) 0.30454(12) 0.0152(4) Uani 0.851(3) 1 d P A 1 H21A H 0.2108 0.2440 0.2749 0.018 Uiso 0.851(3) 1 calc PR A 1 H22A H 0.2046 0.4562 0.2714 0.018 Uiso 0.851(3) 1 calc PR A 1 C3A C 0.12728(13) 0.3455(3) 0.34444(11) 0.0149(4) Uani 0.851(3) 1 d P A 1 H31A H 0.1189 0.4590 0.3703 0.018 Uiso 0.851(3) 1 calc PR A 1 H32A H 0.0833 0.3302 0.3092 0.018 Uiso 0.851(3) 1 calc PR A 1 N4A N 0.12633(13) 0.1966(2) 0.39709(12) 0.0121(4) Uani 0.851(3) 1 d P A 1 C5A C 0.06432(12) 0.2291(3) 0.45257(14) 0.0147(4) Uani 0.851(3) 1 d P A 1 H51A H 0.0468 0.1139 0.4728 0.018 Uiso 0.851(3) 1 calc PR A 1 H52A H 0.0179 0.2864 0.4293 0.018 Uiso 0.851(3) 1 calc PR A 1 C6A C 0.09449(12) 0.3460(3) 0.51310(11) 0.0145(4) Uani 0.851(3) 1 d P A 1 H61A H 0.1073 0.4652 0.4937 0.017 Uiso 0.851(3) 1 calc PR A 1 H62A H 0.0526 0.3602 0.5499 0.017 Uiso 0.851(3) 1 calc PR A 1 N7A N 0.16643(13) 0.2677(3) 0.54749(11) 0.0119(4) Uani 0.851(3) 1 d P A 1 C8A C 0.20782(15) 0.4028(3) 0.59339(11) 0.0140(4) Uani 0.851(3) 1 d P A 1 H81A H 0.2441 0.3415 0.6275 0.017 Uiso 0.851(3) 1 calc PR A 1 H82A H 0.1681 0.4684 0.6222 0.017 Uiso 0.851(3) 1 calc PR A 1 C9A C 0.25461(12) 0.5333(3) 0.54837(11) 0.0151(5) Uani 0.851(3) 1 d P A 1 H91A H 0.2178 0.6003 0.5166 0.018 Uiso 0.851(3) 1 calc PR A 1 H92A H 0.2814 0.6194 0.5808 0.018 Uiso 0.851(3) 1 calc PR A 1 N10A N 0.31506(11) 0.4428(3) 0.50306(12) 0.0130(4) Uani 0.851(3) 1 d P A 1 C11A C 0.33822(13) 0.5665(3) 0.44388(15) 0.0155(5) Uani 0.851(3) 1 d P A 1 H11A H 0.3924 0.5372 0.4276 0.019 Uiso 0.851(3) 1 calc PR A 1 H11B H 0.3387 0.6899 0.4625 0.019 Uiso 0.851(3) 1 calc PR A 1 C12A C 0.28149(13) 0.5540(3) 0.38046(11) 0.0150(4) Uani 0.851(3) 1 d P A 1 H12A H 0.2288 0.5989 0.3950 0.018 Uiso 0.851(3) 1 calc PR A 1 H12B H 0.3009 0.6296 0.3405 0.018 Uiso 0.851(3) 1 calc PR A 1 N1C N 0.2995(7) 0.3973(16) 0.3719(7) 0.011(3) Uiso 0.149(3) 1 d P A 2 C2C C 0.2274(6) 0.4607(15) 0.3354(6) 0.010(2) Uiso 0.149(3) 1 d P A 2 H2C H 0.2423 0.5299 0.2921 0.012 Uiso 0.149(3) 1 calc PR A 2 H2D H 0.1983 0.5409 0.3684 0.012 Uiso 0.149(3) 1 calc PR A 2 C3C C 0.1741(8) 0.3108(17) 0.3131(7) 0.008(3) Uiso 0.149(3) 1 d P A 2 H3C H 0.1269 0.3598 0.2879 0.010 Uiso 0.149(3) 1 calc PR A 2 H3D H 0.2025 0.2333 0.2787 0.010 Uiso 0.149(3) 1 calc PR A 2 N4C N 0.1479(7) 0.2029(17) 0.3758(7) 0.012(3) Uiso 0.149(3) 1 d P A 2 C5C C 0.0853(7) 0.2987(16) 0.4153(6) 0.012(2) Uiso 0.149(3) 1 d P A 2 H5C H 0.0349 0.2907 0.3877 0.014 Uiso 0.149(3) 1 calc PR A 2 H5D H 0.0999 0.4258 0.4192 0.014 Uiso 0.149(3) 1 calc PR A 2 C6C C 0.0735(6) 0.2241(15) 0.4897(7) 0.007(2) Uiso 0.149(3) 1 d P A 2 H6C H 0.0321 0.2939 0.5146 0.008 Uiso 0.149(3) 1 calc PR A 2 H6D H 0.0544 0.1000 0.4856 0.008 Uiso 0.149(3) 1 calc PR A 2 N7C N 0.1466(7) 0.2273(18) 0.5332(7) 0.011(3) Uiso 0.149(3) 1 d P A 2 C8C C 0.1595(8) 0.4055(17) 0.5623(7) 0.018(3) Uiso 0.149(3) 1 d P A 2 H8C H 0.1233 0.4241 0.6035 0.022 Uiso 0.149(3) 1 calc PR A 2 H8D H 0.1456 0.4936 0.5246 0.022 Uiso 0.149(3) 1 calc PR A 2 C9C C 0.2428(8) 0.4395(17) 0.5874(6) 0.009(3) Uiso 0.149(3) 1 d P A 2 H9C H 0.2465 0.5628 0.6058 0.010 Uiso 0.149(3) 1 calc PR A 2 H9D H 0.2552 0.3584 0.6281 0.010 Uiso 0.149(3) 1 calc PR A 2 N10C N 0.3029(7) 0.4144(16) 0.5298(7) 0.010(3) Uiso 0.149(3) 1 d P A 2 C11C C 0.3034(7) 0.5747(16) 0.4865(6) 0.013(2) Uiso 0.149(3) 1 d P A 2 H11C H 0.3358 0.6654 0.5118 0.016 Uiso 0.149(3) 1 calc PR A 2 H11D H 0.2485 0.6208 0.4830 0.016 Uiso 0.149(3) 1 calc PR A 2 C12C C 0.3356(7) 0.5504(17) 0.4102(8) 0.010(3) Uiso 0.149(3) 1 d P A 2 H12C H 0.3254 0.6599 0.3820 0.012 Uiso 0.149(3) 1 calc PR A 2 H12D H 0.3937 0.5330 0.4130 0.012 Uiso 0.149(3) 1 calc PR A 2 C20 C 0.34676(11) 0.3104(2) 0.31537(10) 0.0178(4) Uani 1 1 d . . . H20A H 0.3947 0.3385 0.3443 0.021 Uiso 0.851(3) 1 calc PR A 1 H20B H 0.3503 0.3732 0.2684 0.021 Uiso 0.851(3) 1 calc PR A 1 H20C H 0.4031 0.3374 0.3257 0.021 Uiso 0.149(3) 1 calc PR A 2 H20D H 0.3333 0.3690 0.2689 0.021 Uiso 0.149(3) 1 calc PR A 2 C21 C 0.34058(10) 0.1111(2) 0.30320(10) 0.0158(4) Uani 1 1 d . A . O211 O 0.30497(7) 0.02178(16) 0.35173(7) 0.0155(3) Uani 1 1 d . A . O212 O 0.37024(8) 0.04909(19) 0.24743(7) 0.0241(3) Uani 1 1 d . . . C30 C 0.10942(11) 0.0263(2) 0.35946(10) 0.0176(4) Uani 1 1 d . . . H30A H 0.1426 0.0159 0.3157 0.021 Uiso 0.851(3) 1 calc PR A 1 H30B H 0.0530 0.0217 0.3444 0.021 Uiso 0.851(3) 1 calc PR A 1 H30C H 0.1256 -0.0109 0.3104 0.021 Uiso 0.149(3) 1 calc PR A 2 H30D H 0.0513 0.0439 0.3583 0.021 Uiso 0.149(3) 1 calc PR A 2 C31 C 0.12778(10) -0.1250(2) 0.41141(10) 0.0134(3) Uani 1 1 d . A . O311 O 0.18547(7) -0.09963(16) 0.45518(7) 0.0135(2) Uani 1 1 d . A . O312 O 0.08757(8) -0.26293(17) 0.40862(7) 0.0198(3) Uani 1 1 d . . . C40 C 0.14551(10) 0.1114(2) 0.59389(10) 0.0146(3) Uani 1 1 d . . . H40A H 0.1045 0.0387 0.5693 0.018 Uiso 0.851(3) 1 calc PR A 1 H40B H 0.1236 0.1535 0.6404 0.018 Uiso 0.851(3) 1 calc PR A 1 H40C H 0.0998 0.0301 0.5880 0.018 Uiso 0.149(3) 1 calc PR A 2 H40D H 0.1357 0.1841 0.6376 0.018 Uiso 0.149(3) 1 calc PR A 2 C41 C 0.21911(10) -0.0014(2) 0.60808(9) 0.0122(3) Uani 1 1 d . A . O411 O 0.27909(7) 0.02743(16) 0.56871(6) 0.0133(2) Uani 1 1 d . A . O412 O 0.21610(8) -0.11410(17) 0.65721(7) 0.0173(3) Uani 1 1 d . . . C50 C 0.38531(11) 0.3974(3) 0.55026(11) 0.0202(4) Uani 1 1 d . . . H50A H 0.3672 0.3320 0.5936 0.024 Uiso 0.851(3) 1 calc PR A 1 H50B H 0.4116 0.5081 0.5666 0.024 Uiso 0.851(3) 1 calc PR A 1 H50C H 0.3862 0.3537 0.6008 0.024 Uiso 0.149(3) 1 calc PR A 2 H50D H 0.4074 0.5193 0.5514 0.024 Uiso 0.149(3) 1 calc PR A 2 C51 C 0.44363(11) 0.2844(3) 0.50883(11) 0.0190(4) Uani 1 1 d . A . H511 H 0.4644 0.3529 0.4674 0.023 Uiso 1 1 calc R . . H512 H 0.4888 0.2525 0.5407 0.023 Uiso 1 1 calc R . . N52 N 0.40432(9) 0.1202(2) 0.48216(8) 0.0154(3) Uani 1 1 d . A . H521 H 0.4116 0.0322 0.5161 0.019 Uiso 1 1 calc R . . H522 H 0.4293 0.0843 0.4406 0.019 Uiso 1 1 calc R . . O1W O 0.01769(8) 0.15065(18) 0.20264(7) 0.0214(3) Uani 1 1 d . . . H11W H 0.0359 0.0541 0.1908 0.026 Uiso 1 1 d R . . H12W H -0.0107 0.1785 0.1686 0.026 Uiso 1 1 d R . . O2W O 0.36703(8) 0.70567(19) 0.20714(8) 0.0244(3) Uani 1 1 d . . . H21W H 0.3676 0.8123 0.2195 0.029 Uiso 1 1 d R . . H22W H 0.3220 0.6818 0.1919 0.029 Uiso 1 1 d R . . O3W O 0.07677(8) 0.8000(2) 0.19137(8) 0.0278(3) Uani 1 1 d . . . H31W H 0.0504 0.7419 0.2231 0.033 Uiso 1 1 d R . . H32W H 0.1199 0.7442 0.1815 0.033 Uiso 1 1 d R . . O4W O 0.48005(9) 0.5266(2) 0.12729(8) 0.0291(3) Uani 1 1 d . . . H41W H 0.4874 0.4221 0.1499 0.035 Uiso 1 1 d R . . H42W H 0.4461 0.5883 0.1525 0.035 Uiso 1 1 d R . . O5W O 0.49002(9) 0.6791(2) 0.31674(8) 0.0305(4) Uani 1 1 d . . . H51W H 0.5298 0.6404 0.2936 0.037 Uiso 1 1 d R . . H52W H 0.4532 0.6749 0.2828 0.037 Uiso 1 1 d 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 Yb1 0.00959(4) 0.00835(4) 0.00833(4) 0.00011(3) 0.00064(2) -0.00079(3) N1A 0.0163(10) 0.0105(9) 0.0115(9) -0.0006(7) 0.0023(8) -0.0018(8) C2A 0.0188(12) 0.0149(10) 0.0117(10) 0.0040(8) -0.0006(9) -0.0011(10) C3A 0.0186(10) 0.0106(9) 0.0154(10) 0.0032(8) -0.0043(8) -0.0001(8) N4A 0.0133(10) 0.0093(9) 0.0136(10) 0.0008(7) -0.0012(9) -0.0004(7) C5A 0.0116(10) 0.0160(11) 0.0165(13) 0.0018(9) -0.0005(8) 0.0011(8) C6A 0.0141(10) 0.0148(10) 0.0145(10) 0.0002(8) 0.0021(8) 0.0032(8) N7A 0.0120(9) 0.0119(10) 0.0118(10) 0.0004(8) 0.0005(8) 0.0010(8) C8A 0.0176(12) 0.0136(10) 0.0110(10) -0.0032(8) 0.0038(8) -0.0001(9) C9A 0.0169(10) 0.0121(10) 0.0162(10) -0.0037(8) 0.0009(8) 0.0003(8) N10A 0.0134(9) 0.0131(9) 0.0123(10) -0.0016(8) 0.0002(8) -0.0008(7) C11A 0.0189(11) 0.0108(10) 0.0168(13) -0.0005(9) 0.0001(9) -0.0048(8) C12A 0.0218(11) 0.0089(9) 0.0144(10) 0.0004(8) 0.0009(8) -0.0017(8) C20 0.0229(9) 0.0143(9) 0.0165(9) 0.0003(7) 0.0083(7) 0.0003(7) C21 0.0156(8) 0.0167(9) 0.0152(9) -0.0034(7) 0.0011(7) -0.0010(7) O211 0.0198(6) 0.0129(6) 0.0139(6) -0.0015(5) 0.0042(5) 0.0002(5) O212 0.0301(7) 0.0221(7) 0.0202(7) -0.0082(6) 0.0112(6) -0.0056(6) C30 0.0212(9) 0.0112(8) 0.0202(9) -0.0003(7) -0.0092(7) -0.0025(7) C31 0.0150(8) 0.0107(8) 0.0146(8) -0.0028(7) 0.0006(6) 0.0003(6) O311 0.0142(6) 0.0102(6) 0.0159(6) 0.0008(5) -0.0021(5) -0.0008(5) O312 0.0213(7) 0.0133(6) 0.0247(7) -0.0008(5) -0.0036(5) -0.0063(5) C40 0.0127(8) 0.0185(9) 0.0129(8) 0.0041(7) 0.0031(6) 0.0025(7) C41 0.0144(8) 0.0128(8) 0.0095(8) -0.0017(6) -0.0004(6) -0.0010(6) O411 0.0115(6) 0.0160(6) 0.0123(6) 0.0029(5) 0.0001(4) 0.0007(5) O412 0.0188(6) 0.0181(7) 0.0149(6) 0.0057(5) 0.0029(5) 0.0015(5) C50 0.0149(9) 0.0196(9) 0.0259(10) -0.0068(8) -0.0059(7) -0.0016(7) C51 0.0133(8) 0.0204(9) 0.0232(10) 0.0012(8) -0.0015(7) -0.0031(7) N52 0.0131(7) 0.0173(8) 0.0160(7) 0.0000(6) 0.0015(6) 0.0006(6) O1W 0.0222(7) 0.0222(7) 0.0199(7) -0.0012(6) -0.0032(5) 0.0024(6) O2W 0.0216(7) 0.0197(7) 0.0318(8) -0.0065(6) -0.0055(6) 0.0010(6) O3W 0.0226(7) 0.0262(8) 0.0346(8) 0.0076(6) 0.0102(6) 0.0078(6) O4W 0.0288(8) 0.0327(9) 0.0259(8) 0.0022(7) 0.0109(6) 0.0008(6) O5W 0.0247(7) 0.0453(10) 0.0214(7) -0.0082(7) -0.0016(6) 0.0074(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 Yb1 O311 2.2564(12) . ? Yb1 O211 2.2707(12) . ? Yb1 O411 2.2764(12) . ? Yb1 N52 2.4485(15) . ? Yb1 N4C 2.466(13) . ? Yb1 N7C 2.498(13) . ? Yb1 N7A 2.5157(19) . ? Yb1 N1A 2.5194(18) . ? Yb1 N10C 2.525(12) . ? Yb1 N1C 2.535(12) . ? Yb1 N10A 2.5529(19) . ? Yb1 N4A 2.5622(19) . ? N1A C12A 1.484(3) . ? N1A C2A 1.488(3) . ? N1A C20 1.499(3) . ? C2A C3A 1.510(3) . ? C2A H21A 0.9900 . ? C2A H22A 0.9900 . ? C3A N4A 1.484(3) . ? C3A H31A 0.9900 . ? C3A H32A 0.9900 . ? N4A C30 1.485(3) . ? N4A C5A 1.491(3) . ? C5A C6A 1.509(3) . ? C5A H51A 0.9900 . ? C5A H52A 0.9900 . ? C6A N7A 1.488(3) . ? C6A H61A 0.9900 . ? C6A H62A 0.9900 . ? N7A C8A 1.494(3) . ? N7A C40 1.499(3) . ? C8A C9A 1.513(3) . ? C8A H81A 0.9900 . ? C8A H82A 0.9900 . ? C9A N10A 1.489(3) . ? C9A H91A 0.9900 . ? C9A H92A 0.9900 . ? N10A C11A 1.491(3) . ? N10A C50 1.506(3) . ? C11A C12A 1.511(3) . ? C11A H11A 0.9900 . ? C11A H11B 0.9900 . ? C12A H12A 0.9900 . ? C12A H12B 0.9900 . ? N1C C2C 1.467(15) . ? N1C C20 1.473(12) . ? N1C C12C 1.481(18) . ? C2C C3C 1.498(16) . ? C2C H2C 0.9900 . ? C2C H2D 0.9900 . ? C3C N4C 1.485(18) . ? C3C H3C 0.9900 . ? C3C H3D 0.9900 . ? N4C C5C 1.476(16) . ? N4C C30 1.509(13) . ? C5C C6C 1.500(17) . ? C5C H5C 0.9900 . ? C5C H5D 0.9900 . ? C6C N7C 1.469(18) . ? C6C H6C 0.9900 . ? C6C H6D 0.9900 . ? N7C C40 1.421(13) . ? N7C C8C 1.460(17) . ? C8C C9C 1.498(17) . ? C8C H8C 0.9900 . ? C8C H8D 0.9900 . ? C9C N10C 1.488(17) . ? C9C H9C 0.9900 . ? C9C H9D 0.9900 . ? N10C C50 1.445(11) . ? N10C C11C 1.447(16) . ? C11C C12C 1.526(17) . ? C11C H11C 0.9900 . ? C11C H11D 0.9900 . ? C12C H12C 0.9900 . ? C12C H12D 0.9900 . ? C20 C21 1.520(2) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C20 H20C 0.9900 . ? C20 H20D 0.9900 . ? C21 O212 1.240(2) . ? C21 O211 1.275(2) . ? C30 C31 1.520(2) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C30 H30C 0.9900 . ? C30 H30D 0.9900 . ? C31 O312 1.241(2) . ? C31 O311 1.276(2) . ? C40 C41 1.525(2) . ? C40 H40A 0.9900 . ? C40 H40B 0.9900 . ? C40 H40C 0.9900 . ? C40 H40D 0.9900 . ? C41 O412 1.244(2) . ? C41 O411 1.270(2) . ? C50 C51 1.513(3) . ? C50 H50A 0.9900 . ? C50 H50B 0.9900 . ? C50 H50C 0.9900 . ? C50 H50D 0.9900 . ? C51 N52 1.485(2) . ? C51 H511 0.9900 . ? C51 H512 0.9900 . ? N52 H521 0.9200 . ? N52 H522 0.9200 . ? O1W H11W 0.8193 . ? O1W H12W 0.8163 . ? O2W H21W 0.8343 . ? O2W H22W 0.8281 . ? O3W H31W 0.8590 . ? O3W H32W 0.8602 . ? O4W H41W 0.8984 . ? O4W H42W 0.8751 . ? O5W H51W 0.8506 . ? O5W H52W 0.8801 . ? 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 O311 Yb1 O211 80.82(4) . . ? O311 Yb1 O411 75.87(4) . . ? O211 Yb1 O411 125.29(4) . . ? O311 Yb1 N52 119.86(5) . . ? O211 Yb1 N52 79.43(5) . . ? O411 Yb1 N52 71.07(5) . . ? O311 Yb1 N4C 72.0(3) . . ? O211 Yb1 N4C 79.0(3) . . ? O411 Yb1 N4C 135.3(3) . . ? N52 Yb1 N4C 153.1(3) . . ? O311 Yb1 N7C 75.9(3) . . ? O211 Yb1 N7C 147.1(3) . . ? O411 Yb1 N7C 70.7(3) . . ? N52 Yb1 N7C 132.5(3) . . ? N4C Yb1 N7C 72.0(4) . . ? O311 Yb1 N7A 86.17(6) . . ? O211 Yb1 N7A 158.43(6) . . ? O411 Yb1 N7A 66.93(5) . . ? N52 Yb1 N7A 122.10(7) . . ? O311 Yb1 N1A 125.68(6) . . ? O211 Yb1 N1A 67.14(5) . . ? O411 Yb1 N1A 158.26(6) . . ? N52 Yb1 N1A 96.65(6) . . ? N7A Yb1 N1A 108.14(6) . . ? O311 Yb1 N10C 144.5(3) . . ? O211 Yb1 N10C 134.5(3) . . ? O411 Yb1 N10C 78.0(3) . . ? N52 Yb1 N10C 72.4(3) . . ? N4C Yb1 N10C 113.2(4) . . ? N7C Yb1 N10C 73.0(4) . . ? O311 Yb1 N1C 138.6(3) . . ? O211 Yb1 N1C 72.6(3) . . ? O411 Yb1 N1C 145.5(3) . . ? N52 Yb1 N1C 86.1(3) . . ? N4C Yb1 N1C 72.2(4) . . ? N7C Yb1 N1C 111.5(4) . . ? N10C Yb1 N1C 70.5(4) . . ? O311 Yb1 N10A 156.74(6) . . ? O211 Yb1 N10A 122.40(6) . . ? O411 Yb1 N10A 89.61(6) . . ? N52 Yb1 N10A 70.40(5) . . ? N7A Yb1 N10A 71.31(7) . . ? N1A Yb1 N10A 69.09(7) . . ? O311 Yb1 N4A 66.80(5) . . ? O211 Yb1 N4A 89.18(6) . . ? O411 Yb1 N4A 123.64(6) . . ? N52 Yb1 N4A 165.19(7) . . ? N7A Yb1 N4A 69.82(7) . . ? N1A Yb1 N4A 69.98(7) . . ? N10A Yb1 N4A 108.88(6) . . ? C12A N1A C2A 109.64(17) . . ? C12A N1A C20 110.98(18) . . ? C2A N1A C20 108.20(17) . . ? C12A N1A Yb1 113.32(13) . . ? C2A N1A Yb1 110.54(15) . . ? C20 N1A Yb1 103.95(12) . . ? N1A C2A C3A 111.95(17) . . ? N1A C2A H21A 109.2 . . ? C3A C2A H21A 109.2 . . ? N1A C2A H22A 109.2 . . ? C3A C2A H22A 109.2 . . ? H21A C2A H22A 107.9 . . ? N4A C3A C2A 111.20(18) . . ? N4A C3A H31A 109.4 . . ? C2A C3A H31A 109.4 . . ? N4A C3A H32A 109.4 . . ? C2A C3A H32A 109.4 . . ? H31A C3A H32A 108.0 . . ? C3A N4A C30 110.30(17) . . ? C3A N4A C5A 109.79(17) . . ? C30 N4A C5A 109.30(18) . . ? C3A N4A Yb1 112.26(14) . . ? C30 N4A Yb1 103.91(12) . . ? C5A N4A Yb1 111.12(14) . . ? N4A C5A C6A 111.80(17) . . ? N4A C5A H51A 109.3 . . ? C6A C5A H51A 109.3 . . ? N4A C5A H52A 109.3 . . ? C6A C5A H52A 109.3 . . ? H51A C5A H52A 107.9 . . ? N7A C6A C5A 110.83(18) . . ? N7A C6A H61A 109.5 . . ? C5A C6A H61A 109.5 . . ? N7A C6A H62A 109.5 . . ? C5A C6A H62A 109.5 . . ? H61A C6A H62A 108.1 . . ? C6A N7A C8A 110.45(17) . . ? C6A N7A C40 111.14(18) . . ? C8A N7A C40 108.64(17) . . ? C6A N7A Yb1 112.59(13) . . ? C8A N7A Yb1 109.15(14) . . ? C40 N7A Yb1 104.65(12) . . ? N7A C8A C9A 111.87(17) . . ? N7A C8A H81A 109.2 . . ? C9A C8A H81A 109.2 . . ? N7A C8A H82A 109.2 . . ? C9A C8A H82A 109.2 . . ? H81A C8A H82A 107.9 . . ? N10A C9A C8A 112.04(18) . . ? N10A C9A H91A 109.2 . . ? C8A C9A H91A 109.2 . . ? N10A C9A H92A 109.2 . . ? C8A C9A H92A 109.2 . . ? H91A C9A H92A 107.9 . . ? C9A N10A C11A 108.18(17) . . ? C9A N10A C50 108.49(17) . . ? C11A N10A C50 110.95(17) . . ? C9A N10A Yb1 110.56(13) . . ? C11A N10A Yb1 113.00(14) . . ? C50 N10A Yb1 105.59(12) . . ? N10A C11A C12A 111.28(17) . . ? N10A C11A H11A 109.4 . . ? C12A C11A H11A 109.4 . . ? N10A C11A H11B 109.4 . . ? C12A C11A H11B 109.4 . . ? H11A C11A H11B 108.0 . . ? N1A C12A C11A 111.00(18) . . ? N1A C12A H12A 109.4 . . ? C11A C12A H12A 109.4 . . ? N1A C12A H12B 109.4 . . ? C11A C12A H12B 109.4 . . ? H12A C12A H12B 108.0 . . ? C2C N1C C20 105.6(9) . . ? C2C N1C C12C 107.7(10) . . ? C20 N1C C12C 117.5(9) . . ? C2C N1C Yb1 108.5(8) . . ? C20 N1C Yb1 104.1(6) . . ? C12C N1C Yb1 112.9(8) . . ? N1C C2C C3C 112.1(10) . . ? N1C C2C H2C 109.2 . . ? C3C C2C H2C 109.2 . . ? N1C C2C H2D 109.2 . . ? C3C C2C H2D 109.2 . . ? H2C C2C H2D 107.9 . . ? N4C C3C C2C 112.2(10) . . ? N4C C3C H3C 109.2 . . ? C2C C3C H3C 109.2 . . ? N4C C3C H3D 109.2 . . ? C2C C3C H3D 109.2 . . ? H3C C3C H3D 107.9 . . ? C5C N4C C3C 109.7(11) . . ? C5C N4C C30 102.8(9) . . ? C3C N4C C30 117.1(10) . . ? C5C N4C Yb1 110.2(8) . . ? C3C N4C Yb1 109.3(8) . . ? C30 N4C Yb1 107.5(7) . . ? N4C C5C C6C 111.8(10) . . ? N4C C5C H5C 109.2 . . ? C6C C5C H5C 109.2 . . ? N4C C5C H5D 109.2 . . ? C6C C5C H5D 109.2 . . ? H5C C5C H5D 107.9 . . ? N7C C6C C5C 112.3(10) . . ? N7C C6C H6C 109.1 . . ? C5C C6C H6C 109.1 . . ? N7C C6C H6D 109.1 . . ? C5C C6C H6D 109.1 . . ? H6C C6C H6D 107.9 . . ? C40 N7C C8C 106.0(10) . . ? C40 N7C C6C 114.0(10) . . ? C8C N7C C6C 109.8(11) . . ? C40 N7C Yb1 108.3(7) . . ? C8C N7C Yb1 108.6(8) . . ? C6C N7C Yb1 109.9(8) . . ? N7C C8C C9C 114.1(11) . . ? N7C C8C H8C 108.7 . . ? C9C C8C H8C 108.7 . . ? N7C C8C H8D 108.7 . . ? C9C C8C H8D 108.7 . . ? H8C C8C H8D 107.6 . . ? N10C C9C C8C 113.5(10) . . ? N10C C9C H9C 108.9 . . ? C8C C9C H9C 108.9 . . ? N10C C9C H9D 108.9 . . ? C8C C9C H9D 108.9 . . ? H9C C9C H9D 107.7 . . ? C50 N10C C11C 102.1(9) . . ? C50 N10C C9C 118.9(9) . . ? C11C N10C C9C 107.3(10) . . ? C50 N10C Yb1 109.1(6) . . ? C11C N10C Yb1 111.8(8) . . ? C9C N10C Yb1 107.6(8) . . ? N10C C11C C12C 114.5(10) . . ? N10C C11C H11C 108.6 . . ? C12C C11C H11C 108.6 . . ? N10C C11C H11D 108.6 . . ? C12C C11C H11D 108.6 . . ? H11C C11C H11D 107.6 . . ? N1C C12C C11C 112.8(10) . . ? N1C C12C H12C 109.0 . . ? C11C C12C H12C 109.0 . . ? N1C C12C H12D 109.0 . . ? C11C C12C H12D 109.0 . . ? H12C C12C H12D 107.8 . . ? N1C C20 C21 120.4(5) . . ? N1A C20 C21 107.52(15) . . ? N1A C20 H20A 110.2 . . ? C21 C20 H20A 110.2 . . ? N1A C20 H20B 110.2 . . ? C21 C20 H20B 110.2 . . ? H20A C20 H20B 108.5 . . ? N1C C20 H20C 107.2 . . ? C21 C20 H20C 107.2 . . ? N1C C20 H20D 107.2 . . ? C21 C20 H20D 107.2 . . ? H20C C20 H20D 106.9 . . ? O212 C21 O211 125.56(17) . . ? O212 C21 C20 117.82(16) . . ? O211 C21 C20 116.62(15) . . ? C21 O211 Yb1 122.47(11) . . ? N4A C30 C31 108.22(15) . . ? N4C C30 C31 116.6(5) . . ? N4A C30 H30A 110.1 . . ? C31 C30 H30A 110.1 . . ? N4A C30 H30B 110.1 . . ? C31 C30 H30B 110.1 . . ? H30A C30 H30B 108.4 . . ? N4C C30 H30C 108.1 . . ? C31 C30 H30C 108.1 . . ? N4C C30 H30D 108.1 . . ? C31 C30 H30D 108.1 . . ? H30C C30 H30D 107.3 . . ? O312 C31 O311 124.45(17) . . ? O312 C31 C30 119.44(16) . . ? O311 C31 C30 116.11(15) . . ? C31 O311 Yb1 124.32(11) . . ? N7C C40 C41 117.5(5) . . ? N7A C40 C41 109.89(14) . . ? N7A C40 H40A 109.7 . . ? C41 C40 H40A 109.7 . . ? N7A C40 H40B 109.7 . . ? C41 C40 H40B 109.7 . . ? H40A C40 H40B 108.2 . . ? N7C C40 H40C 107.9 . . ? C41 C40 H40C 107.9 . . ? N7C C40 H40D 107.9 . . ? C41 C40 H40D 107.9 . . ? H40C C40 H40D 107.2 . . ? O412 C41 O411 124.90(16) . . ? O412 C41 C40 117.87(15) . . ? O411 C41 C40 117.23(15) . . ? C41 O411 Yb1 119.69(11) . . ? N10C C50 C51 123.1(5) . . ? N10A C50 C51 110.26(16) . . ? N10A C50 H50A 109.6 . . ? C51 C50 H50A 109.6 . . ? N10A C50 H50B 109.6 . . ? C51 C50 H50B 109.6 . . ? H50A C50 H50B 108.1 . . ? N10C C50 H50C 106.6 . . ? C51 C50 H50C 106.6 . . ? N10C C50 H50D 106.6 . . ? C51 C50 H50D 106.6 . . ? H50C C50 H50D 106.5 . . ? N52 C51 C50 110.20(14) . . ? N52 C51 H511 109.6 . . ? C50 C51 H511 109.6 . . ? N52 C51 H512 109.6 . . ? C50 C51 H512 109.6 . . ? H511 C51 H512 108.1 . . ? C51 N52 Yb1 115.65(11) . . ? C51 N52 H521 108.4 . . ? Yb1 N52 H521 108.4 . . ? C51 N52 H522 108.4 . . ? Yb1 N52 H522 108.4 . . ? H521 N52 H522 107.4 . . ? H11W O1W H12W 103.9 . . ? H21W O2W H22W 108.1 . . ? H31W O3W H32W 109.9 . . ? H41W O4W H42W 107.7 . . ? H51W O5W H52W 100.6 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.383 _refine_diff_density_min -0.853 _refine_diff_density_rms 0.067 _database_code_depnum_ccdc_archive 'CCDC 933967' ####################################################################### # # 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_do3aaeme _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H33 N5 O6, 6(H2 O)' _chemical_formula_sum 'C17 H45 N5 O12' _chemical_formula_weight 511.58 _chemical_compound_source 'synthesized by the authors' 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 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 9.4479(7) _cell_length_b 17.7199(14) _cell_length_c 15.5379(9) _cell_angle_alpha 90.00 _cell_angle_beta 106.573(2) _cell_angle_gamma 90.00 _cell_volume 2493.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 8716 _cell_measurement_theta_min 2.5259 _cell_measurement_theta_max 27.4983 _exptl_crystal_description pelet _exptl_crystal_colour colourless _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.46 _exptl_crystal_size_min 0.33 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.363 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1112 _exptl_absorpt_coefficient_mu 0.114 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.91 _exptl_absorpt_correction_T_max 0.96 _exptl_absorpt_process_details 'SADABS V2012/1 (Bruker AXS Inc.)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 8.3333 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21324 _diffrn_reflns_av_R_equivalents 0.0232 _diffrn_reflns_av_sigmaI/netI 0.0237 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5723 _reflns_number_gt 4765 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Instrument Service v2012.12.0.0' _computing_cell_refinement 'SAINT V8.27B (Bruker AXS Inc., 2012)' _computing_data_reduction 'SAINT V8.27B (Bruker AXS Inc., 2012)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _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^)+(0.0579P)^2^+0.9668P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5723 _refine_ls_number_parameters 391 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0520 _refine_ls_R_factor_gt 0.0415 _refine_ls_wR_factor_ref 0.1129 _refine_ls_wR_factor_gt 0.1065 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _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 N1 N 0.14571(12) 0.81107(7) 0.61839(7) 0.0178(2) Uani 1 1 d . . . H11 H 0.1942(19) 0.8133(9) 0.6742(12) 0.021(4) Uiso 1 1 d . . . C2 C 0.25555(16) 0.80506(8) 0.56469(9) 0.0217(3) Uani 1 1 d . . . H21 H 0.2852 0.8563 0.5512 0.026 Uiso 1 1 calc R . . H22 H 0.2089 0.7793 0.5070 0.026 Uiso 1 1 calc R . . C3 C 0.39083(16) 0.76137(8) 0.61618(9) 0.0216(3) Uani 1 1 d . . . H31 H 0.3605 0.7111 0.6325 0.026 Uiso 1 1 calc R . . H32 H 0.4569 0.7537 0.5776 0.026 Uiso 1 1 calc R . . N4 N 0.47111(12) 0.80198(6) 0.69833(7) 0.0168(2) Uani 1 1 d . . . C5 C 0.58250(16) 0.85235(8) 0.67993(9) 0.0221(3) Uani 1 1 d . . . H51 H 0.5368 0.8816 0.6247 0.027 Uiso 1 1 calc R . . H52 H 0.6632 0.8216 0.6691 0.027 Uiso 1 1 calc R . . C6 C 0.64713(15) 0.90683(8) 0.75681(10) 0.0238(3) Uani 1 1 d . . . H61 H 0.7152 0.8789 0.8070 0.029 Uiso 1 1 calc R . . H62 H 0.7054 0.9458 0.7364 0.029 Uiso 1 1 calc R . . N7 N 0.53103(13) 0.94482(7) 0.79025(7) 0.0194(2) Uani 1 1 d . . . H71 H 0.470(2) 0.9101(10) 0.7943(11) 0.025(4) Uiso 1 1 d . . . C8 C 0.44602(16) 1.00453(8) 0.72787(9) 0.0215(3) Uani 1 1 d . . . H81 H 0.4285 0.9879 0.6649 0.026 Uiso 1 1 calc R . . H82 H 0.5044 1.0518 0.7362 0.026 Uiso 1 1 calc R . . C9 C 0.29930(16) 1.01917(8) 0.74653(9) 0.0226(3) Uani 1 1 d . . . H91 H 0.3172 1.0308 0.8111 0.027 Uiso 1 1 calc R . . H92 H 0.2519 1.0638 0.7117 0.027 Uiso 1 1 calc R . . N10 N 0.19789(13) 0.95393(6) 0.72275(7) 0.0185(2) Uani 1 1 d . . . C11 C 0.12974(16) 0.95245(8) 0.62476(9) 0.0215(3) Uani 1 1 d . . . H111 H 0.2076 0.9603 0.5945 0.026 Uiso 1 1 calc R . . H112 H 0.0589 0.9948 0.6079 0.026 Uiso 1 1 calc R . . C12 C 0.04953(15) 0.87927(8) 0.59119(9) 0.0225(3) Uani 1 1 d . . . H121 H -0.0367 0.8747 0.6150 0.027 Uiso 1 1 calc R . . H122 H 0.0123 0.8810 0.5249 0.027 Uiso 1 1 calc R . . C20 C 0.05425(17) 0.74054(8) 0.60726(9) 0.0243(3) Uani 1 1 d . . . H201 H 0.1203 0.6965 0.6109 0.029 Uiso 1 1 calc R . . H202 H -0.0165 0.7407 0.5464 0.029 Uiso 1 1 calc R . . C21 C -0.03253(16) 0.72987(9) 0.67598(9) 0.0243(3) Uani 1 1 d . . . O211 O -0.03757(11) 0.78197(6) 0.72982(7) 0.0267(2) Uani 1 1 d . . . O212 O -0.09370(14) 0.66706(7) 0.67034(8) 0.0378(3) Uani 1 1 d . . . C30 C 0.53259(15) 0.74855(8) 0.77158(9) 0.0192(3) Uani 1 1 d . . . H301 H 0.6083 0.7746 0.8198 0.023 Uiso 1 1 calc R . . H302 H 0.5818 0.7069 0.7489 0.023 Uiso 1 1 calc R . . C31 C 0.41437(15) 0.71562(8) 0.81077(8) 0.0175(3) Uani 1 1 d . . . O311 O 0.28611(10) 0.74050(6) 0.78562(6) 0.0211(2) Uani 1 1 d . . . O312 O 0.45712(11) 0.66364(6) 0.86880(7) 0.0245(2) Uani 1 1 d . . . C40 C 0.59472(17) 0.97340(8) 0.88460(9) 0.0247(3) Uani 1 1 d . . . H401 H 0.5419 1.0196 0.8936 0.030 Uiso 1 1 calc R . . H402 H 0.7002 0.9862 0.8948 0.030 Uiso 1 1 calc R . . C41 C 0.57936(15) 0.91266(8) 0.95119(9) 0.0206(3) Uani 1 1 d . . . O411 O 0.48345(11) 0.86327(6) 0.92104(6) 0.0247(2) Uani 1 1 d . . . O412 O 0.66232(12) 0.91955(6) 1.02949(7) 0.0292(3) Uani 1 1 d . . . C50 C 0.08139(16) 0.96026(9) 0.76853(10) 0.0248(3) Uani 1 1 d . . . H501 H -0.0053 0.9303 0.7350 0.030 Uiso 1 1 calc R . . H502 H 0.0501 1.0137 0.7674 0.030 Uiso 1 1 calc R . . C51 C 0.13035(17) 0.93328(8) 0.86480(9) 0.0241(3) Uani 1 1 d . . . H511 H 0.2150 0.9642 0.8989 0.029 Uiso 1 1 calc R . . H512 H 0.0487 0.9406 0.8922 0.029 Uiso 1 1 calc R . . N53 N 0.17423(14) 0.85251(7) 0.87216(8) 0.0209(3) Uani 1 1 d . . . H531 H 0.106(2) 0.8245(11) 0.8272(14) 0.038(5) Uiso 1 1 d . . . H532 H 0.266(2) 0.8466(11) 0.8608(13) 0.039(5) Uiso 1 1 d . . . C54 C 0.18814(17) 0.82231(9) 0.96336(9) 0.0255(3) Uani 1 1 d . . . H541 H 0.0917 0.8241 0.9752 0.031 Uiso 1 1 calc R . . H542 H 0.2591 0.8529 1.0081 0.031 Uiso 1 1 calc R . . H543 H 0.2228 0.7700 0.9670 0.031 Uiso 1 1 calc R . . O1W O 0.20118(14) 0.90958(8) 0.36222(11) 0.0310(3) Uani 1 1 d . . . H11W H 0.122(3) 0.8865(14) 0.3684(15) 0.053(6) Uiso 1 1 d . . . H12W H 0.196(4) 0.918(2) 0.313(3) 0.024(10) Uiso 0.50 1 d P . . H13W H 0.230(5) 0.937(3) 0.395(4) 0.042(14) Uiso 0.50 1 d P . . O2W O 0.04596(15) 0.07033(8) 0.97299(9) 0.0408(3) Uani 1 1 d . . . H21W H 0.138(3) 0.0738(14) 0.9689(15) 0.067(8) Uiso 1 1 d . . . H22W H 0.0234 0.0244 0.9713 0.057(15) Uiso 0.50 1 d PR . . H23W H -0.027(6) 0.080(2) 0.917(4) 0.047(12) Uiso 0.50 1 d P . . O3W O 0.43123(14) 0.80083(9) 0.38245(8) 0.0399(3) Uani 1 1 d . . . H31W H 0.420(3) 0.7793(15) 0.3314(19) 0.066(8) Uiso 1 1 d . . . H32W H 0.363(3) 0.8323(17) 0.3747(19) 0.076(9) Uiso 1 1 d . . . O4W O 0.71336(16) 0.86782(8) 0.44170(9) 0.0383(3) Uani 1 1 d . . . H41W H 0.632(3) 0.8458(14) 0.4126(17) 0.060(7) Uiso 1 1 d . . . H42W H 0.779(3) 0.8551(15) 0.4123(18) 0.070(8) Uiso 1 1 d . . . O5WA O 0.6400(9) 1.0041(4) 0.5020(4) 0.0299(10) Uani 0.50 1 d P . . O5WB O 0.6541(14) 0.9872(6) 0.5223(7) 0.074(3) Uani 0.50 1 d P . . H51W H 0.676(4) 0.957(2) 0.497(2) 0.089 Uiso 1 1 d . . . H52W H 0.685(8) 1.022(4) 0.544(5) 0.089 Uiso 0.50 1 d P . . H53W H 0.580(8) 0.992(5) 0.515(6) 0.089 Uiso 0.50 1 d P . . O6W O 0.67762(17) 0.58300(7) 0.68418(11) 0.0330(3) Uani 1 1 d . . . H61W H 0.743(3) 0.6128(13) 0.6801(14) 0.041(6) Uiso 1 1 d . . . H62W H 0.615(5) 0.586(2) 0.647(3) 0.031(13) Uiso 0.50 1 d P . . H63W H 0.680(4) 0.583(2) 0.741(3) 0.030(10) Uiso 0.50 1 d P . . 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 0.0162(6) 0.0207(6) 0.0145(5) -0.0006(4) 0.0012(4) -0.0034(4) C2 0.0251(7) 0.0259(7) 0.0142(6) -0.0009(5) 0.0059(5) -0.0026(6) C3 0.0273(7) 0.0203(7) 0.0194(6) -0.0028(5) 0.0101(6) 0.0010(6) N4 0.0168(5) 0.0156(5) 0.0183(5) 0.0016(4) 0.0056(4) 0.0008(4) C5 0.0198(7) 0.0226(7) 0.0269(7) 0.0044(6) 0.0114(6) 0.0015(6) C6 0.0168(7) 0.0240(7) 0.0296(7) 0.0052(6) 0.0051(6) -0.0032(6) N7 0.0194(6) 0.0183(6) 0.0181(5) 0.0023(4) 0.0016(4) -0.0059(5) C8 0.0250(7) 0.0176(7) 0.0201(6) 0.0038(5) 0.0033(5) -0.0029(6) C9 0.0280(8) 0.0160(7) 0.0228(6) 0.0001(5) 0.0055(6) 0.0009(6) N10 0.0194(6) 0.0188(6) 0.0176(5) 0.0009(4) 0.0059(4) 0.0028(5) C11 0.0216(7) 0.0215(7) 0.0194(6) 0.0053(5) 0.0026(5) 0.0038(6) C12 0.0173(7) 0.0271(7) 0.0201(6) 0.0040(6) 0.0006(5) 0.0019(6) C20 0.0252(7) 0.0233(7) 0.0219(6) -0.0048(5) 0.0025(6) -0.0099(6) C21 0.0182(7) 0.0293(8) 0.0215(6) 0.0026(6) -0.0009(5) -0.0060(6) O211 0.0185(5) 0.0345(6) 0.0260(5) 0.0016(4) 0.0048(4) -0.0018(4) O212 0.0390(7) 0.0363(7) 0.0365(6) 0.0021(5) 0.0081(5) -0.0186(5) C30 0.0182(7) 0.0166(6) 0.0230(6) 0.0042(5) 0.0064(5) 0.0051(5) C31 0.0201(7) 0.0161(6) 0.0162(6) -0.0022(5) 0.0053(5) -0.0002(5) O311 0.0169(5) 0.0255(5) 0.0212(5) 0.0004(4) 0.0060(4) 0.0008(4) O312 0.0257(5) 0.0249(5) 0.0225(5) 0.0079(4) 0.0064(4) 0.0009(4) C40 0.0272(8) 0.0229(7) 0.0187(6) 0.0001(5) -0.0020(6) -0.0075(6) C41 0.0195(7) 0.0220(7) 0.0198(6) 0.0005(5) 0.0047(5) -0.0006(5) O411 0.0236(5) 0.0271(5) 0.0212(5) 0.0012(4) 0.0032(4) -0.0092(4) O412 0.0308(6) 0.0348(6) 0.0181(5) -0.0001(4) 0.0006(4) -0.0101(5) C50 0.0219(7) 0.0290(8) 0.0251(7) 0.0030(6) 0.0092(6) 0.0085(6) C51 0.0275(8) 0.0245(7) 0.0228(6) -0.0016(6) 0.0112(6) 0.0037(6) N53 0.0196(6) 0.0242(6) 0.0185(5) -0.0020(5) 0.0048(5) 0.0004(5) C54 0.0272(8) 0.0279(8) 0.0212(6) 0.0015(6) 0.0064(6) 0.0006(6) O1W 0.0253(6) 0.0340(7) 0.0322(7) -0.0075(6) 0.0058(5) -0.0057(5) O2W 0.0298(7) 0.0526(9) 0.0427(7) -0.0070(6) 0.0145(6) 0.0063(6) O3W 0.0323(7) 0.0530(8) 0.0299(6) -0.0071(6) 0.0018(5) 0.0136(6) O4W 0.0323(7) 0.0398(7) 0.0453(7) -0.0098(6) 0.0152(6) 0.0010(6) O5WA 0.046(2) 0.019(2) 0.0269(18) -0.0091(14) 0.0136(14) -0.0055(16) O5WB 0.106(6) 0.053(6) 0.075(6) -0.028(3) 0.045(5) -0.034(5) O6W 0.0287(7) 0.0333(7) 0.0414(8) -0.0067(6) 0.0169(7) -0.0081(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 C12 1.4985(18) . ? N1 C20 1.5011(18) . ? N1 C2 1.5094(17) . ? N1 H11 0.859(17) . ? C2 C3 1.513(2) . ? C2 H21 0.9900 . ? C2 H22 0.9900 . ? C3 N4 1.4731(17) . ? C3 H31 0.9900 . ? C3 H32 0.9900 . ? N4 C30 1.4671(17) . ? N4 C5 1.4688(18) . ? C5 C6 1.522(2) . ? C5 H51 0.9900 . ? C5 H52 0.9900 . ? C6 N7 1.5004(19) . ? C6 H61 0.9900 . ? C6 H62 0.9900 . ? N7 C8 1.5033(18) . ? N7 C40 1.5049(17) . ? N7 H71 0.859(19) . ? C8 C9 1.517(2) . ? C8 H81 0.9900 . ? C8 H82 0.9900 . ? C9 N10 1.4794(18) . ? C9 H91 0.9900 . ? C9 H92 0.9900 . ? N10 C11 1.4746(17) . ? N10 C50 1.4754(18) . ? C11 C12 1.517(2) . ? C11 H111 0.9900 . ? C11 H112 0.9900 . ? C12 H121 0.9900 . ? C12 H122 0.9900 . ? C20 C21 1.532(2) . ? C20 H201 0.9900 . ? C20 H202 0.9900 . ? C21 O212 1.2455(18) . ? C21 O211 1.2558(19) . ? C30 C31 1.5319(19) . ? C30 H301 0.9900 . ? C30 H302 0.9900 . ? C31 O311 1.2432(17) . ? C31 O312 1.2714(16) . ? C40 C41 1.528(2) . ? C40 H401 0.9900 . ? C40 H402 0.9900 . ? C41 O411 1.2506(17) . ? C41 O412 1.2512(17) . ? C50 C51 1.5116(19) . ? C50 H501 0.9900 . ? C50 H502 0.9900 . ? C51 N53 1.4855(19) . ? C51 H511 0.9900 . ? C51 H512 0.9900 . ? N53 C54 1.4850(18) . ? N53 H531 0.94(2) . ? N53 H532 0.94(2) . ? C54 H541 0.9800 . ? C54 H542 0.9800 . ? C54 H543 0.9800 . ? O1W H11W 0.88(3) . ? O1W H12W 0.77(5) . ? O1W H13W 0.70(6) . ? O2W H21W 0.89(3) . ? O2W H22W 0.8401 . ? O2W H23W 0.96(6) . ? O3W H31W 0.86(3) . ? O3W H32W 0.84(3) . ? O4W H41W 0.86(3) . ? O4W H42W 0.89(3) . ? O5WA H51W 0.91(4) . ? O5WA H52W 0.74(8) . ? O5WA H53W 0.69(8) . ? O5WB H51W 0.73(4) . ? O5WB H52W 0.72(8) . ? O5WB H53W 0.68(7) . ? O6W H61W 0.83(3) . ? O6W H62W 0.70(5) . ? O6W H63W 0.87(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 N1 C20 110.86(11) . . ? C12 N1 C2 110.99(11) . . ? C20 N1 C2 109.97(11) . . ? C12 N1 H11 110.7(11) . . ? C20 N1 H11 106.2(11) . . ? C2 N1 H11 108.0(11) . . ? N1 C2 C3 110.74(11) . . ? N1 C2 H21 109.5 . . ? C3 C2 H21 109.5 . . ? N1 C2 H22 109.5 . . ? C3 C2 H22 109.5 . . ? H21 C2 H22 108.1 . . ? N4 C3 C2 110.89(11) . . ? N4 C3 H31 109.5 . . ? C2 C3 H31 109.5 . . ? N4 C3 H32 109.5 . . ? C2 C3 H32 109.5 . . ? H31 C3 H32 108.0 . . ? C30 N4 C5 113.34(11) . . ? C30 N4 C3 110.42(11) . . ? C5 N4 C3 110.40(11) . . ? N4 C5 C6 112.46(11) . . ? N4 C5 H51 109.1 . . ? C6 C5 H51 109.1 . . ? N4 C5 H52 109.1 . . ? C6 C5 H52 109.1 . . ? H51 C5 H52 107.8 . . ? N7 C6 C5 112.78(11) . . ? N7 C6 H61 109.0 . . ? C5 C6 H61 109.0 . . ? N7 C6 H62 109.0 . . ? C5 C6 H62 109.0 . . ? H61 C6 H62 107.8 . . ? C6 N7 C8 113.67(11) . . ? C6 N7 C40 111.08(11) . . ? C8 N7 C40 112.51(11) . . ? C6 N7 H71 106.1(12) . . ? C8 N7 H71 107.7(12) . . ? C40 N7 H71 105.1(12) . . ? N7 C8 C9 110.26(11) . . ? N7 C8 H81 109.6 . . ? C9 C8 H81 109.6 . . ? N7 C8 H82 109.6 . . ? C9 C8 H82 109.6 . . ? H81 C8 H82 108.1 . . ? N10 C9 C8 112.37(11) . . ? N10 C9 H91 109.1 . . ? C8 C9 H91 109.1 . . ? N10 C9 H92 109.1 . . ? C8 C9 H92 109.1 . . ? H91 C9 H92 107.9 . . ? C11 N10 C50 109.46(11) . . ? C11 N10 C9 109.43(11) . . ? C50 N10 C9 109.83(11) . . ? N10 C11 C12 113.47(11) . . ? N10 C11 H111 108.9 . . ? C12 C11 H111 108.9 . . ? N10 C11 H112 108.9 . . ? C12 C11 H112 108.9 . . ? H111 C11 H112 107.7 . . ? N1 C12 C11 112.90(11) . . ? N1 C12 H121 109.0 . . ? C11 C12 H121 109.0 . . ? N1 C12 H122 109.0 . . ? C11 C12 H122 109.0 . . ? H121 C12 H122 107.8 . . ? N1 C20 C21 115.30(12) . . ? N1 C20 H201 108.4 . . ? C21 C20 H201 108.4 . . ? N1 C20 H202 108.4 . . ? C21 C20 H202 108.4 . . ? H201 C20 H202 107.5 . . ? O212 C21 O211 126.78(14) . . ? O212 C21 C20 113.02(13) . . ? O211 C21 C20 120.20(13) . . ? N4 C30 C31 112.46(11) . . ? N4 C30 H301 109.1 . . ? C31 C30 H301 109.1 . . ? N4 C30 H302 109.1 . . ? C31 C30 H302 109.1 . . ? H301 C30 H302 107.8 . . ? O311 C31 O312 124.32(13) . . ? O311 C31 C30 119.72(12) . . ? O312 C31 C30 115.95(12) . . ? N7 C40 C41 109.49(11) . . ? N7 C40 H401 109.8 . . ? C41 C40 H401 109.8 . . ? N7 C40 H402 109.8 . . ? C41 C40 H402 109.8 . . ? H401 C40 H402 108.2 . . ? O411 C41 O412 128.21(13) . . ? O411 C41 C40 115.97(12) . . ? O412 C41 C40 115.81(12) . . ? N10 C50 C51 113.15(12) . . ? N10 C50 H501 108.9 . . ? C51 C50 H501 108.9 . . ? N10 C50 H502 108.9 . . ? C51 C50 H502 108.9 . . ? H501 C50 H502 107.8 . . ? N53 C51 C50 112.39(12) . . ? N53 C51 H511 109.1 . . ? C50 C51 H511 109.1 . . ? N53 C51 H512 109.1 . . ? C50 C51 H512 109.1 . . ? H511 C51 H512 107.9 . . ? C54 N53 C51 111.56(11) . . ? C54 N53 H531 111.9(12) . . ? C51 N53 H531 109.5(12) . . ? C54 N53 H532 107.7(12) . . ? C51 N53 H532 110.2(12) . . ? H531 N53 H532 105.7(17) . . ? N53 C54 H541 109.5 . . ? N53 C54 H542 109.5 . . ? H541 C54 H542 109.5 . . ? N53 C54 H543 109.5 . . ? H541 C54 H543 109.5 . . ? H542 C54 H543 109.5 . . ? H11W O1W H12W 113(3) . . ? H11W O1W H13W 114(4) . . ? H12W O1W H13W 119(5) . . ? H21W O2W H22W 107.9 . . ? H21W O2W H23W 113(3) . . ? H22W O2W H23W 92.1 . . ? H31W O3W H32W 106(3) . . ? H41W O4W H42W 105(2) . . ? H51W O5WA H52W 109(6) . . ? H51W O5WA H53W 95(7) . . ? H52W O5WA H53W 101(9) . . ? H51W O5WB H52W 137(7) . . ? H51W O5WB H53W 116(9) . . ? H52W O5WB H53W 104(10) . . ? H61W O6W H62W 112(4) . . ? H61W O6W H63W 106(3) . . ? H62W O6W H63W 127(4) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.354 _refine_diff_density_min -0.224 _refine_diff_density_rms 0.046 _database_code_depnum_ccdc_archive 'CCDC 952384' ####################################################################### # # 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_me2do3aae _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H35 N5 O6, 3.5(H2 O)' _chemical_formula_sum 'C18 H42 N5 O9.50' _chemical_formula_weight 480.57 _chemical_compound_source 'synthesized by the authors' 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 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 7.4798(2) _cell_length_b 15.9561(4) _cell_length_c 20.0951(6) _cell_angle_alpha 90.00 _cell_angle_beta 91.5670(10) _cell_angle_gamma 90.00 _cell_volume 2397.42(11) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9877 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 27.51 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.331 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1044 _exptl_absorpt_coefficient_mu 0.107 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.91 _exptl_absorpt_correction_T_max 0.97 _exptl_absorpt_process_details 'SADABS V2012/1 (Bruker AXS Inc.)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 8.3333 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30750 _diffrn_reflns_av_R_equivalents 0.0259 _diffrn_reflns_av_sigmaI/netI 0.0193 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5503 _reflns_number_gt 4686 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Instrument Service v2012.12.0.3' _computing_cell_refinement 'SAINT V8.27B (Bruker AXS Inc., 2012)' _computing_data_reduction 'SAINT V8.27B (Bruker AXS Inc., 2012)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0439P)^2^+1.0015P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5503 _refine_ls_number_parameters 348 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0455 _refine_ls_R_factor_gt 0.0370 _refine_ls_wR_factor_ref 0.0952 _refine_ls_wR_factor_gt 0.0902 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.010 _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 0.84392(13) 0.68189(6) 0.09943(5) 0.0144(2) Uani 1 1 d . . . H11 H 0.786(2) 0.7169(10) 0.1252(8) 0.022(4) Uiso 1 1 d . . . C2 C 0.77384(16) 0.69443(7) 0.02934(6) 0.0173(2) Uani 1 1 d . . . H21 H 0.6485 0.6745 0.0263 0.021 Uiso 1 1 calc R . . H22 H 0.8446 0.6593 -0.0008 0.021 Uiso 1 1 calc R . . C3 C 0.77980(15) 0.78447(7) 0.00521(6) 0.0150(2) Uani 1 1 d . . . H31 H 0.9062 0.8015 0.0009 0.018 Uiso 1 1 calc R . . H32 H 0.7215 0.7878 -0.0395 0.018 Uiso 1 1 calc R . . N4 N 0.69134(12) 0.84342(6) 0.04970(5) 0.01381(19) Uani 1 1 d . . . C5 C 0.73618(15) 0.93086(7) 0.03346(6) 0.0158(2) Uani 1 1 d . . . H51 H 0.6342 0.9677 0.0439 0.019 Uiso 1 1 calc R . . H52 H 0.7579 0.9356 -0.0148 0.019 Uiso 1 1 calc R . . C6 C 0.90173(15) 0.95938(7) 0.07282(6) 0.0156(2) Uani 1 1 d . . . H61 H 1.0058 0.9249 0.0605 0.019 Uiso 1 1 calc R . . H62 H 0.9282 1.0186 0.0622 0.019 Uiso 1 1 calc R . . N7 N 0.87037(12) 0.95064(6) 0.14578(5) 0.01341(19) Uani 1 1 d . . . H71 H 0.8137(19) 0.9027(9) 0.1512(7) 0.018(3) Uiso 1 1 d . . . C8 C 1.03980(15) 0.94786(7) 0.18777(6) 0.0172(2) Uani 1 1 d . . . H81 H 1.0115 0.9594 0.2347 0.021 Uiso 1 1 calc R . . H82 H 1.1222 0.9922 0.1728 0.021 Uiso 1 1 calc R . . C9 C 1.13124(15) 0.86356(7) 0.18330(6) 0.0166(2) Uani 1 1 d . . . H91 H 1.1665 0.8538 0.1368 0.020 Uiso 1 1 calc R . . H92 H 1.2414 0.8641 0.2117 0.020 Uiso 1 1 calc R . . N10 N 1.01488(12) 0.79428(6) 0.20447(5) 0.0143(2) Uani 1 1 d . . . C11 C 1.09047(15) 0.71450(7) 0.18061(6) 0.0172(2) Uani 1 1 d . . . H111 H 1.0451 0.6677 0.2077 0.021 Uiso 1 1 calc R . . H112 H 1.2223 0.7159 0.1863 0.021 Uiso 1 1 calc R . . C12 C 1.04098(15) 0.69924(7) 0.10787(6) 0.0163(2) Uani 1 1 d . . . H121 H 1.0726 0.7491 0.0813 0.020 Uiso 1 1 calc R . . H122 H 1.1097 0.6509 0.0913 0.020 Uiso 1 1 calc R . . C20 C 0.79598(16) 0.59561(7) 0.12218(6) 0.0181(2) Uani 1 1 d . . . H201 H 0.8881 0.5754 0.1546 0.022 Uiso 1 1 calc R . . H202 H 0.7939 0.5570 0.0836 0.022 Uiso 1 1 calc R . . C21 C 0.61336(16) 0.59488(8) 0.15446(6) 0.0206(3) Uani 1 1 d . . . O211 O 0.55243(13) 0.66372(6) 0.17153(5) 0.0322(2) Uani 1 1 d . . . O212 O 0.54900(13) 0.52288(6) 0.16183(5) 0.0312(2) Uani 1 1 d . . . C30 C 0.49822(15) 0.83068(8) 0.05569(6) 0.0162(2) Uani 1 1 d . . . H301 H 0.4576 0.8666 0.0925 0.019 Uiso 1 1 calc R . . H302 H 0.4792 0.7718 0.0694 0.019 Uiso 1 1 calc R . . C31 C 0.37535(15) 0.84793(7) -0.00544(6) 0.0148(2) Uani 1 1 d . . . O311 O 0.21201(11) 0.84080(6) 0.00374(5) 0.0270(2) Uani 1 1 d . . . O312 O 0.44477(11) 0.86806(6) -0.05929(4) 0.02198(19) Uani 1 1 d . . . C40 C 0.74629(16) 1.01632(7) 0.17105(6) 0.0169(2) Uani 1 1 d . . . H401 H 0.6850 1.0446 0.1330 0.020 Uiso 1 1 calc R . . H402 H 0.8157 1.0590 0.1965 0.020 Uiso 1 1 calc R . . C41 C 0.60794(15) 0.97679(7) 0.21565(6) 0.0158(2) Uani 1 1 d . . . O411 O 0.60900(11) 0.89856(5) 0.22004(4) 0.02077(19) Uani 1 1 d . . . O412 O 0.50354(12) 1.02684(6) 0.24281(4) 0.0227(2) Uani 1 1 d . . . C50 C 1.00373(16) 0.79288(8) 0.27776(6) 0.0205(3) Uani 1 1 d . . . H501 H 0.9921 0.8511 0.2941 0.025 Uiso 1 1 calc R . . H502 H 1.1164 0.7695 0.2970 0.025 Uiso 1 1 calc R . . C51 C 0.84684(16) 0.74120(8) 0.30220(6) 0.0203(2) Uani 1 1 d . . . H511 H 0.8100 0.7010 0.2669 0.024 Uiso 1 1 calc R . . H512 H 0.8875 0.7084 0.3416 0.024 Uiso 1 1 calc R . . N52 N 0.68758(14) 0.79236(7) 0.32046(6) 0.0220(2) Uani 1 1 d . . . H522 H 0.657(3) 0.8300(12) 0.2845(10) 0.049(5) Uiso 1 1 d . . . C53 C 0.7216(2) 0.84360(10) 0.38134(9) 0.0385(4) Uani 1 1 d . . . H531 H 0.6154 0.8773 0.3904 0.058 Uiso 1 1 calc R . . H532 H 0.8238 0.8808 0.3745 0.058 Uiso 1 1 calc R . . H533 H 0.7479 0.8065 0.4192 0.058 Uiso 1 1 calc R . . C54 C 0.52920(18) 0.73725(10) 0.33008(8) 0.0310(3) Uani 1 1 d . . . H541 H 0.5559 0.6972 0.3660 0.046 Uiso 1 1 calc R . . H542 H 0.5015 0.7067 0.2888 0.046 Uiso 1 1 calc R . . H543 H 0.4262 0.7716 0.3419 0.046 Uiso 1 1 calc R . . O1W O 0.71643(13) 0.88617(6) 0.85272(5) 0.0284(2) Uani 1 1 d . . . H11W H 0.654(3) 0.9092(12) 0.8197(11) 0.050(6) Uiso 1 1 d . . . H12W H 0.630(3) 0.8806(13) 0.8857(11) 0.054(6) Uiso 1 1 d . . . O2W O 0.20752(15) 0.46153(7) 0.15846(6) 0.0338(2) Uani 1 1 d . . . H21W H 0.142(3) 0.4825(12) 0.1917(10) 0.045(5) Uiso 1 1 d . . . H22W H 0.310(3) 0.4856(15) 0.1642(12) 0.069(7) Uiso 1 1 d . . . O3W O 0.15956(17) 0.51701(8) 0.03069(6) 0.0421(3) Uani 1 1 d . . . H31W H 0.153(4) 0.4970(18) 0.0771(15) 0.101(9) Uiso 1 1 d . . . H32W H 0.036(6) 0.500(3) 0.010(3) 0.052(12) Uiso 0.50 1 d P . . H33W H 0.287(5) 0.522(2) 0.0162(17) 0.031(8) Uiso 0.50 1 d P . . O4W O 0.5095(3) 0.46765(19) 0.02460(14) 0.0470(6) Uani 0.50 1 d P . . H41W H 0.417(6) 0.506(3) 0.013(2) 0.044(10) Uiso 0.50 1 d P . . H42W H 0.516(7) 0.488(3) 0.068(3) 0.088(17) Uiso 0.50 1 d P . . 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 0.0153(5) 0.0122(5) 0.0157(5) 0.0006(4) 0.0015(4) 0.0018(4) C2 0.0220(6) 0.0149(6) 0.0149(6) -0.0003(4) -0.0019(4) 0.0000(4) C3 0.0156(5) 0.0157(5) 0.0139(5) 0.0018(4) 0.0013(4) 0.0015(4) N4 0.0121(4) 0.0141(5) 0.0152(5) 0.0007(4) 0.0008(3) 0.0007(3) C5 0.0174(5) 0.0132(5) 0.0167(6) 0.0011(4) -0.0022(4) 0.0011(4) C6 0.0172(5) 0.0163(5) 0.0134(5) 0.0010(4) 0.0016(4) -0.0023(4) N7 0.0144(4) 0.0110(5) 0.0149(5) 0.0002(4) 0.0008(3) -0.0014(4) C8 0.0172(5) 0.0170(6) 0.0171(6) -0.0004(4) -0.0039(4) -0.0037(4) C9 0.0120(5) 0.0188(6) 0.0189(6) 0.0024(4) -0.0009(4) -0.0030(4) N10 0.0132(4) 0.0147(5) 0.0150(5) 0.0015(4) 0.0000(3) -0.0011(4) C11 0.0154(5) 0.0160(6) 0.0200(6) 0.0035(4) -0.0012(4) 0.0029(4) C12 0.0138(5) 0.0158(6) 0.0195(6) 0.0012(4) 0.0025(4) 0.0017(4) C20 0.0209(6) 0.0120(5) 0.0213(6) 0.0035(4) 0.0015(5) -0.0001(4) C21 0.0197(6) 0.0260(6) 0.0160(6) 0.0034(5) 0.0000(5) -0.0018(5) O211 0.0297(5) 0.0313(6) 0.0363(6) -0.0021(4) 0.0138(4) 0.0023(4) O212 0.0259(5) 0.0283(5) 0.0395(6) 0.0084(4) 0.0041(4) -0.0085(4) C30 0.0125(5) 0.0209(6) 0.0152(5) 0.0027(4) 0.0022(4) 0.0007(4) C31 0.0146(5) 0.0125(5) 0.0174(6) -0.0004(4) -0.0005(4) 0.0004(4) O311 0.0130(4) 0.0377(6) 0.0300(5) 0.0072(4) -0.0013(4) -0.0024(4) O312 0.0177(4) 0.0323(5) 0.0158(4) 0.0047(4) -0.0008(3) 0.0020(4) C40 0.0216(6) 0.0111(5) 0.0180(6) -0.0002(4) 0.0017(4) 0.0029(4) C41 0.0169(5) 0.0184(6) 0.0119(5) 0.0000(4) -0.0026(4) 0.0030(4) O411 0.0227(4) 0.0165(4) 0.0233(5) 0.0036(3) 0.0049(3) 0.0016(3) O412 0.0252(5) 0.0235(5) 0.0195(4) -0.0027(3) 0.0035(3) 0.0079(4) C50 0.0214(6) 0.0252(6) 0.0148(6) 0.0013(5) -0.0006(4) -0.0056(5) C51 0.0235(6) 0.0177(6) 0.0201(6) 0.0009(5) 0.0048(5) -0.0007(5) N52 0.0218(5) 0.0200(5) 0.0243(6) 0.0054(4) 0.0005(4) 0.0011(4) C53 0.0412(9) 0.0323(8) 0.0426(9) -0.0143(7) 0.0118(7) -0.0013(7) C54 0.0215(6) 0.0332(8) 0.0384(8) 0.0032(6) 0.0062(6) -0.0039(5) O1W 0.0202(5) 0.0350(6) 0.0300(5) 0.0102(4) 0.0019(4) 0.0006(4) O2W 0.0262(5) 0.0452(7) 0.0303(6) -0.0036(5) 0.0059(4) -0.0037(5) O3W 0.0375(7) 0.0565(8) 0.0323(6) -0.0086(5) 0.0017(5) 0.0052(5) O4W 0.0317(12) 0.0714(19) 0.0380(14) -0.0103(12) 0.0017(10) -0.0035(12) _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 C20 1.4973(14) . ? N1 C2 1.5026(15) . ? N1 C12 1.5048(14) . ? C2 C3 1.5173(16) . ? C3 N4 1.4676(15) . ? N4 C30 1.4670(14) . ? N4 C5 1.4736(14) . ? C5 C6 1.5206(15) . ? C6 N7 1.4976(15) . ? N7 C40 1.4978(14) . ? N7 C8 1.5039(14) . ? C8 C9 1.5128(16) . ? C9 N10 1.4767(14) . ? N10 C50 1.4776(15) . ? N10 C11 1.4782(15) . ? C11 C12 1.5176(16) . ? C20 C21 1.5281(17) . ? C21 O211 1.2412(16) . ? C21 O212 1.2560(16) . ? C30 C31 1.5388(16) . ? C31 O311 1.2458(14) . ? C31 O312 1.2549(15) . ? C40 C41 1.5241(16) . ? C41 O411 1.2513(14) . ? C41 O412 1.2526(14) . ? C50 C51 1.5263(17) . ? C51 N52 1.4980(16) . ? N52 C53 1.4875(19) . ? N52 C54 1.4923(17) . ? O4W O4W 1.434(6) 3_665 ? 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 C20 N1 C2 109.16(9) . . ? C20 N1 C12 112.13(9) . . ? C2 N1 C12 113.37(9) . . ? N1 C2 C3 114.40(9) . . ? N4 C3 C2 113.24(9) . . ? C30 N4 C3 115.00(9) . . ? C30 N4 C5 112.33(9) . . ? C3 N4 C5 111.27(9) . . ? N4 C5 C6 110.81(9) . . ? N7 C6 C5 109.52(9) . . ? C6 N7 C40 112.45(9) . . ? C6 N7 C8 113.57(9) . . ? C40 N7 C8 110.54(9) . . ? N7 C8 C9 111.61(9) . . ? N10 C9 C8 112.18(9) . . ? C9 N10 C50 110.39(9) . . ? C9 N10 C11 108.51(9) . . ? C50 N10 C11 110.04(9) . . ? N10 C11 C12 111.42(9) . . ? N1 C12 C11 110.52(9) . . ? N1 C20 C21 111.16(10) . . ? O211 C21 O212 129.20(12) . . ? O211 C21 C20 116.73(11) . . ? O212 C21 C20 114.02(11) . . ? N4 C30 C31 118.53(9) . . ? O311 C31 O312 125.56(11) . . ? O311 C31 C30 115.61(10) . . ? O312 C31 C30 118.82(10) . . ? N7 C40 C41 110.29(9) . . ? O411 C41 O412 127.46(11) . . ? O411 C41 C40 116.82(10) . . ? O412 C41 C40 115.70(10) . . ? N10 C50 C51 113.19(10) . . ? N52 C51 C50 114.08(10) . . ? C53 N52 C54 109.62(11) . . ? C53 N52 C51 112.44(11) . . ? C54 N52 C51 110.49(10) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.361 _refine_diff_density_min -0.202 _refine_diff_density_rms 0.042 _database_code_depnum_ccdc_archive 'CCDC 952385' ####################################################################### # # 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_tkdl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H31 N5 O6, 5(H2 O)' _chemical_formula_sum 'C16 H41 N5 O11' _chemical_formula_weight 479.54 _chemical_compound_source 'synthesized by the authors' 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 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.80380(10) _cell_length_b 16.7236(3) _cell_length_c 17.8081(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.1431(12) _cell_angle_gamma 90.00 _cell_volume 2322.47(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 9965 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 27.53 _exptl_crystal_description bar _exptl_crystal_colour colourless _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.371 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1040 _exptl_absorpt_coefficient_mu 0.115 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 34482 _diffrn_reflns_av_R_equivalents 0.0258 _diffrn_reflns_av_sigmaI/netI 0.0204 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 27.59 _reflns_number_total 5358 _reflns_number_gt 4408 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0406P)^2^+0.8593P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5358 _refine_ls_number_parameters 349 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0462 _refine_ls_R_factor_gt 0.0344 _refine_ls_wR_factor_ref 0.0873 _refine_ls_wR_factor_gt 0.0814 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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 N1 N 0.35242(12) 0.26824(6) 0.28521(6) 0.0146(2) Uani 1 1 d . . . H11 H 0.3709(18) 0.3106(9) 0.2559(9) 0.020(4) Uiso 1 1 d . . . C2 C 0.32363(16) 0.29912(7) 0.36294(7) 0.0181(2) Uani 1 1 d . . . H21 H 0.4334 0.3113 0.3876 0.022 Uiso 1 1 calc R . . H22 H 0.2690 0.2579 0.3919 0.022 Uiso 1 1 calc R . . C3 C 0.21227(16) 0.37364(7) 0.36155(7) 0.0181(2) Uani 1 1 d . . . H31 H 0.0953 0.3589 0.3473 0.022 Uiso 1 1 calc R . . H32 H 0.2121 0.3965 0.4116 0.022 Uiso 1 1 calc R . . N4 N 0.27271(12) 0.43407(6) 0.30882(5) 0.0146(2) Uani 1 1 d . . . C5 C 0.14541(15) 0.49874(7) 0.30012(7) 0.0174(2) Uani 1 1 d . . . H51 H 0.2030 0.5483 0.2883 0.021 Uiso 1 1 calc R . . H52 H 0.0880 0.5061 0.3470 0.021 Uiso 1 1 calc R . . C6 C 0.01489(15) 0.47911(7) 0.23837(7) 0.0172(2) Uani 1 1 d . . . H61 H -0.0724 0.5204 0.2357 0.021 Uiso 1 1 calc R . . H62 H -0.0405 0.4288 0.2494 0.021 Uiso 1 1 calc R . . N7 N 0.09987(12) 0.47314(6) 0.16384(5) 0.0130(2) Uani 1 1 d . . . H71 H 0.205(2) 0.4532(8) 0.1721(8) 0.018(4) Uiso 1 1 d . . . C8 C -0.00102(15) 0.41860(7) 0.11176(7) 0.0162(2) Uani 1 1 d . . . H81 H 0.0369 0.4264 0.0610 0.019 Uiso 1 1 calc R . . H82 H -0.1211 0.4335 0.1123 0.019 Uiso 1 1 calc R . . C9 C 0.01588(14) 0.33070(7) 0.13173(7) 0.0160(2) Uani 1 1 d . . . H91 H -0.0309 0.3221 0.1808 0.019 Uiso 1 1 calc R . . H92 H -0.0521 0.2996 0.0955 0.019 Uiso 1 1 calc R . . N10 N 0.19376(12) 0.30125(6) 0.13301(5) 0.0139(2) Uani 1 1 d . . . C11 C 0.20042(15) 0.22142(7) 0.16844(7) 0.0166(2) Uani 1 1 d . . . H111 H 0.3040 0.1943 0.1540 0.020 Uiso 1 1 calc R . . H112 H 0.1032 0.1902 0.1498 0.020 Uiso 1 1 calc R . . C12 C 0.19793(14) 0.22524(7) 0.25323(7) 0.0158(2) Uani 1 1 d . . . H121 H 0.0950 0.2527 0.2680 0.019 Uiso 1 1 calc R . . H122 H 0.1953 0.1714 0.2734 0.019 Uiso 1 1 calc R . . C20 C 0.51195(15) 0.21853(7) 0.28415(8) 0.0202(3) Uani 1 1 d . . . H201 H 0.4956 0.1752 0.2484 0.024 Uiso 1 1 calc R . . H202 H 0.5346 0.1954 0.3335 0.024 Uiso 1 1 calc R . . C21 C 0.66526(15) 0.26941(8) 0.26233(7) 0.0184(2) Uani 1 1 d . . . O211 O 0.63278(11) 0.33380(5) 0.22924(5) 0.02104(19) Uani 1 1 d . . . O212 O 0.80869(11) 0.24038(7) 0.27886(6) 0.0320(2) Uani 1 1 d . . . C30 C 0.44039(15) 0.46655(7) 0.33178(7) 0.0171(2) Uani 1 1 d . . . H301 H 0.5139 0.4231 0.3492 0.020 Uiso 1 1 calc R . . H302 H 0.4266 0.5028 0.3736 0.020 Uiso 1 1 calc R . . C31 C 0.52837(15) 0.51110(7) 0.26894(7) 0.0146(2) Uani 1 1 d . . . O311 O 0.46400(11) 0.50841(5) 0.20318(5) 0.01848(18) Uani 1 1 d . . . O312 O 0.66205(11) 0.54839(5) 0.28915(5) 0.01926(19) Uani 1 1 d . . . C40 C 0.11659(15) 0.55462(7) 0.12938(7) 0.0147(2) Uani 1 1 d . . . H401 H 0.1676 0.5906 0.1666 0.018 Uiso 1 1 calc R . . H402 H 0.0029 0.5747 0.1158 0.018 Uiso 1 1 calc R . . C41 C 0.22495(14) 0.55578(7) 0.05967(6) 0.0140(2) Uani 1 1 d . . . O411 O 0.29770(11) 0.49327(5) 0.03950(5) 0.01914(19) Uani 1 1 d . . . O412 O 0.22962(11) 0.62158(5) 0.02636(5) 0.01954(19) Uani 1 1 d . . . C50 C 0.25715(15) 0.29497(7) 0.05615(7) 0.0177(2) Uani 1 1 d . . . H501 H 0.2107 0.3388 0.0261 0.021 Uiso 1 1 calc R . . H502 H 0.2159 0.2454 0.0336 0.021 Uiso 1 1 calc R . . C51 C 0.45095(16) 0.29687(7) 0.05445(7) 0.0194(3) Uani 1 1 d . . . H511 H 0.4976 0.2533 0.0848 0.023 Uiso 1 1 calc R . . H512 H 0.4854 0.2888 0.0032 0.023 Uiso 1 1 calc R . . N52 N 0.52403(14) 0.37394(6) 0.08322(6) 0.0159(2) Uani 1 1 d . . . H521 H 0.453(2) 0.4158(10) 0.0764(9) 0.028(4) Uiso 1 1 d . . . H522 H 0.557(2) 0.3702(9) 0.1335(10) 0.026(4) Uiso 1 1 d . . . H523 H 0.620(2) 0.3848(9) 0.0564(9) 0.026(4) Uiso 1 1 d . . . O1W O 0.31293(13) 0.08142(6) 0.39467(6) 0.0265(2) Uani 1 1 d . . . H11W H 0.325(2) 0.0549(11) 0.4353(12) 0.042(5) Uiso 1 1 d . . . H12W H 0.376(3) 0.0590(12) 0.3639(12) 0.047(6) Uiso 1 1 d . . . O2W O 0.20487(13) 0.04443(6) 0.06672(6) 0.0268(2) Uani 1 1 d . . . H21W H 0.246(3) 0.0408(11) 0.1128(12) 0.046(5) Uiso 1 1 d . . . H22W H 0.187(2) -0.0032(13) 0.0507(11) 0.049(6) Uiso 1 1 d . . . O3W O 0.08398(14) 0.76105(6) 0.07199(7) 0.0317(2) Uani 1 1 d . . . H31W H 0.120(2) 0.7607(12) 0.1187(13) 0.050(6) Uiso 1 1 d . . . H32W H 0.128(3) 0.7187(13) 0.0537(12) 0.053(6) Uiso 1 1 d . . . O4W O 0.12329(14) 0.59958(7) 0.49189(7) 0.0318(2) Uani 1 1 d . . . H41W H 0.110(3) 0.6424(14) 0.5151(13) 0.059(6) Uiso 1 1 d . . . H42W H 0.023(3) 0.5897(12) 0.4688(12) 0.056(6) Uiso 1 1 d . . . O5W O 0.50458(16) 0.12191(7) 0.00878(7) 0.0363(3) Uani 1 1 d . . . H51W H 0.425(3) 0.0884(13) 0.0281(13) 0.064(7) Uiso 1 1 d . . . H52W H 0.615(3) 0.1033(13) 0.0224(14) 0.071(7) 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 N1 0.0111(4) 0.0151(5) 0.0178(5) 0.0044(4) 0.0011(4) -0.0012(4) C2 0.0196(6) 0.0205(6) 0.0142(6) 0.0038(5) -0.0006(5) -0.0046(5) C3 0.0198(6) 0.0201(6) 0.0145(6) 0.0012(5) 0.0041(5) -0.0040(5) N4 0.0144(5) 0.0157(5) 0.0137(5) 0.0008(4) 0.0017(4) -0.0026(4) C5 0.0205(6) 0.0172(6) 0.0148(6) -0.0022(5) 0.0063(5) 0.0001(5) C6 0.0144(5) 0.0205(6) 0.0172(6) 0.0014(5) 0.0068(5) 0.0013(4) N7 0.0104(4) 0.0147(5) 0.0141(5) 0.0007(4) 0.0016(4) 0.0018(4) C8 0.0132(5) 0.0167(6) 0.0183(6) 0.0004(5) -0.0037(4) -0.0002(4) C9 0.0129(5) 0.0156(5) 0.0194(6) 0.0015(5) -0.0007(4) -0.0019(4) N10 0.0139(5) 0.0140(5) 0.0138(5) 0.0005(4) 0.0009(4) 0.0001(4) C11 0.0164(5) 0.0137(5) 0.0196(6) 0.0000(5) 0.0005(5) -0.0007(4) C12 0.0106(5) 0.0170(6) 0.0197(6) 0.0027(5) -0.0001(4) -0.0022(4) C20 0.0124(5) 0.0188(6) 0.0293(7) 0.0050(5) -0.0004(5) 0.0027(5) C21 0.0141(5) 0.0284(7) 0.0126(5) 0.0017(5) 0.0010(4) 0.0005(5) O211 0.0187(4) 0.0235(5) 0.0210(4) 0.0040(4) 0.0013(4) -0.0025(3) O212 0.0117(4) 0.0517(6) 0.0328(6) 0.0174(5) 0.0017(4) 0.0041(4) C30 0.0185(6) 0.0196(6) 0.0130(5) -0.0003(5) -0.0003(4) -0.0059(5) C31 0.0149(5) 0.0126(5) 0.0166(6) -0.0007(4) 0.0032(4) 0.0011(4) O311 0.0176(4) 0.0235(4) 0.0144(4) 0.0021(3) 0.0013(3) -0.0029(3) O312 0.0164(4) 0.0205(4) 0.0209(4) 0.0004(4) 0.0008(3) -0.0051(3) C40 0.0148(5) 0.0135(5) 0.0159(6) 0.0013(4) 0.0015(4) 0.0018(4) C41 0.0117(5) 0.0169(6) 0.0132(5) -0.0005(4) -0.0015(4) -0.0007(4) O411 0.0218(4) 0.0175(4) 0.0184(4) -0.0006(3) 0.0050(3) 0.0043(3) O412 0.0234(4) 0.0168(4) 0.0188(4) 0.0034(3) 0.0059(4) 0.0020(3) C50 0.0200(6) 0.0195(6) 0.0136(6) -0.0026(5) 0.0004(5) -0.0034(5) C51 0.0208(6) 0.0176(6) 0.0201(6) -0.0041(5) 0.0059(5) -0.0012(5) N52 0.0149(5) 0.0164(5) 0.0165(5) 0.0003(4) 0.0023(4) 0.0000(4) O1W 0.0262(5) 0.0336(5) 0.0202(5) 0.0034(4) 0.0072(4) 0.0087(4) O2W 0.0294(5) 0.0259(5) 0.0245(5) 0.0002(4) -0.0054(4) 0.0015(4) O3W 0.0404(6) 0.0243(5) 0.0304(6) -0.0026(4) 0.0004(5) 0.0130(5) O4W 0.0283(5) 0.0290(6) 0.0376(6) -0.0058(5) -0.0031(5) 0.0003(4) O5W 0.0352(6) 0.0306(6) 0.0429(7) 0.0103(5) -0.0008(5) 0.0020(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 N1 C20 1.4977(15) . ? N1 C12 1.4979(15) . ? N1 C2 1.5020(15) . ? N1 H11 0.894(16) . ? C2 C3 1.5190(17) . ? C2 H21 0.9700 . ? C2 H22 0.9700 . ? C3 N4 1.4693(15) . ? C3 H31 0.9700 . ? C3 H32 0.9700 . ? N4 C30 1.4610(15) . ? N4 C5 1.4728(15) . ? C5 C6 1.5068(17) . ? C5 H51 0.9700 . ? C5 H52 0.9700 . ? C6 N7 1.5090(14) . ? C6 H61 0.9700 . ? C6 H62 0.9700 . ? N7 C40 1.5023(14) . ? N7 C8 1.5024(15) . ? N7 H71 0.892(15) . ? C8 C9 1.5170(16) . ? C8 H81 0.9700 . ? C8 H82 0.9700 . ? C9 N10 1.4723(14) . ? C9 H91 0.9700 . ? C9 H92 0.9700 . ? N10 C50 1.4764(15) . ? N10 C11 1.4767(15) . ? C11 C12 1.5121(17) . ? C11 H111 0.9700 . ? C11 H112 0.9700 . ? C12 H121 0.9700 . ? C12 H122 0.9700 . ? C20 C21 1.5301(17) . ? C20 H201 0.9700 . ? C20 H202 0.9700 . ? C21 O212 1.2451(15) . ? C21 O211 1.2490(15) . ? C30 C31 1.5284(16) . ? C30 H301 0.9700 . ? C30 H302 0.9700 . ? C31 O312 1.2565(14) . ? C31 O311 1.2578(15) . ? C40 C41 1.5280(16) . ? C40 H401 0.9700 . ? C40 H402 0.9700 . ? C41 O411 1.2487(14) . ? C41 O412 1.2513(14) . ? C50 C51 1.5141(17) . ? C50 H501 0.9700 . ? C50 H502 0.9700 . ? C51 N52 1.4923(16) . ? C51 H511 0.9700 . ? C51 H512 0.9700 . ? N52 H521 0.900(17) . ? N52 H522 0.925(17) . ? N52 H523 0.920(17) . ? O1W H11W 0.85(2) . ? O1W H12W 0.84(2) . ? O2W H21W 0.87(2) . ? O2W H22W 0.86(2) . ? O3W H31W 0.87(2) . ? O3W H32W 0.86(2) . ? O4W H41W 0.84(2) . ? O4W H42W 0.89(2) . ? O5W H51W 0.91(2) . ? O5W H52W 0.94(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C20 N1 C12 112.72(9) . . ? C20 N1 C2 110.82(9) . . ? C12 N1 C2 111.68(9) . . ? C20 N1 H11 106.2(9) . . ? C12 N1 H11 107.7(10) . . ? C2 N1 H11 107.4(9) . . ? N1 C2 C3 111.85(10) . . ? N1 C2 H21 109.2 . . ? C3 C2 H21 109.2 . . ? N1 C2 H22 109.2 . . ? C3 C2 H22 109.2 . . ? H21 C2 H22 107.9 . . ? N4 C3 C2 112.19(9) . . ? N4 C3 H31 109.2 . . ? C2 C3 H31 109.2 . . ? N4 C3 H32 109.2 . . ? C2 C3 H32 109.2 . . ? H31 C3 H32 107.9 . . ? C30 N4 C3 112.48(9) . . ? C30 N4 C5 110.49(9) . . ? C3 N4 C5 109.93(9) . . ? N4 C5 C6 110.59(10) . . ? N4 C5 H51 109.5 . . ? C6 C5 H51 109.5 . . ? N4 C5 H52 109.5 . . ? C6 C5 H52 109.5 . . ? H51 C5 H52 108.1 . . ? C5 C6 N7 110.42(9) . . ? C5 C6 H61 109.6 . . ? N7 C6 H61 109.6 . . ? C5 C6 H62 109.6 . . ? N7 C6 H62 109.6 . . ? H61 C6 H62 108.1 . . ? C40 N7 C8 110.48(9) . . ? C40 N7 C6 110.31(9) . . ? C8 N7 C6 110.23(9) . . ? C40 N7 H71 108.2(9) . . ? C8 N7 H71 109.4(9) . . ? C6 N7 H71 108.1(9) . . ? N7 C8 C9 113.86(9) . . ? N7 C8 H81 108.8 . . ? C9 C8 H81 108.8 . . ? N7 C8 H82 108.8 . . ? C9 C8 H82 108.8 . . ? H81 C8 H82 107.7 . . ? N10 C9 C8 113.67(9) . . ? N10 C9 H91 108.8 . . ? C8 C9 H91 108.8 . . ? N10 C9 H92 108.8 . . ? C8 C9 H92 108.8 . . ? H91 C9 H92 107.7 . . ? C9 N10 C50 110.97(9) . . ? C9 N10 C11 109.09(9) . . ? C50 N10 C11 108.92(9) . . ? N10 C11 C12 112.77(10) . . ? N10 C11 H111 109.0 . . ? C12 C11 H111 109.0 . . ? N10 C11 H112 109.0 . . ? C12 C11 H112 109.0 . . ? H111 C11 H112 107.8 . . ? N1 C12 C11 111.08(9) . . ? N1 C12 H121 109.4 . . ? C11 C12 H121 109.4 . . ? N1 C12 H122 109.4 . . ? C11 C12 H122 109.4 . . ? H121 C12 H122 108.0 . . ? N1 C20 C21 110.66(10) . . ? N1 C20 H201 109.5 . . ? C21 C20 H201 109.5 . . ? N1 C20 H202 109.5 . . ? C21 C20 H202 109.5 . . ? H201 C20 H202 108.1 . . ? O212 C21 O211 127.76(12) . . ? O212 C21 C20 115.32(11) . . ? O211 C21 C20 116.90(10) . . ? N4 C30 C31 113.48(10) . . ? N4 C30 H301 108.9 . . ? C31 C30 H301 108.9 . . ? N4 C30 H302 108.9 . . ? C31 C30 H302 108.9 . . ? H301 C30 H302 107.7 . . ? O312 C31 O311 125.65(11) . . ? O312 C31 C30 115.03(10) . . ? O311 C31 C30 119.31(10) . . ? N7 C40 C41 113.74(9) . . ? N7 C40 H401 108.8 . . ? C41 C40 H401 108.8 . . ? N7 C40 H402 108.8 . . ? C41 C40 H402 108.8 . . ? H401 C40 H402 107.7 . . ? O411 C41 O412 125.33(11) . . ? O411 C41 C40 119.63(10) . . ? O412 C41 C40 115.02(10) . . ? N10 C50 C51 112.74(10) . . ? N10 C50 H501 109.0 . . ? C51 C50 H501 109.0 . . ? N10 C50 H502 109.0 . . ? C51 C50 H502 109.0 . . ? H501 C50 H502 107.8 . . ? N52 C51 C50 112.37(10) . . ? N52 C51 H511 109.1 . . ? C50 C51 H511 109.1 . . ? N52 C51 H512 109.1 . . ? C50 C51 H512 109.1 . . ? H511 C51 H512 107.9 . . ? C51 N52 H521 113.5(10) . . ? C51 N52 H522 111.3(10) . . ? H521 N52 H522 109.5(14) . . ? C51 N52 H523 107.4(10) . . ? H521 N52 H523 106.7(14) . . ? H522 N52 H523 108.2(14) . . ? H11W O1W H12W 105.9(18) . . ? H21W O2W H22W 107.4(18) . . ? H31W O3W H32W 103.7(19) . . ? H41W O4W H42W 105.4(19) . . ? H51W O5W H52W 109.3(19) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.59 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.299 _refine_diff_density_min -0.214 _refine_diff_density_rms 0.043 _database_code_depnum_ccdc_archive 'CCDC 952386'