# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2009 data_global _journal_name_full 'New J.Chem.' _journal_coden_Cambridge 0440 _publ_contact_author_name 'Hu, Kai' _publ_contact_author_email kathyhk0406@yahoo.com.cn _publ_section_title ; A Cucurbit[8]uril Inclusion Complex with 1,7-dimethyl-1,4,7,10-tetraazacyclododecane tetrahydrochloride ; loop_ _publ_author_name X.Wu K.Hu X.Meng G.Cheng # Attachment '- 070921em.cif' data_I _database_code_depnum_ccdc_archive 'CCDC 689822' #TrackingRef '- 070921em.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C48 H48 N32 O16, C10 H28 N4, 16(H2 O), 4(Cl)' _chemical_formula_sum 'C58 H108 Cl4 N36 O38' _chemical_formula_weight 1963.38 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M 'R -3' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 37.8856(10) _cell_length_b 37.8856(10) _cell_length_c 16.3396(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 20310.5(14) _cell_formula_units_Z 9 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 8706 _cell_measurement_theta_min 2.15 _cell_measurement_theta_max 19.95 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.524 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 9828.0 _exptl_absorpt_coefficient_mu 0.239 _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 295(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 65128 _diffrn_reflns_av_R_equivalents 0.0883 _diffrn_reflns_av_sigmaI/netI 0.0641 _diffrn_reflns_limit_h_min -45 _diffrn_reflns_limit_h_max 45 _diffrn_reflns_limit_k_min -45 _diffrn_reflns_limit_k_max 42 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 25.00 _reflns_number_total 7859 _reflns_number_gt 4099 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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. Owing to the serious crystal deterioration, although the crystals selected were sealed in capillaries with mother liquid, some solvent molecules could not be suitably modeled which resulted in a solvent-accessible void of 169.0\%A^3^ in the structure. The tetra-azacyclododecane guest molecule is disordered by a symmetry of inversion center. Owing to some large thermal factors in the guest molecule, hydrogen atoms were not added in the final refinement. However, the contribution of these hydrogen atoms should be included in the reported formula, formula weight, etc., data in the CIF. The moiety formula of the complex should be C48 H48 N32 O16, C10 H28 N4, 16(H2 O), 4(CL). And some related items has been corrected in the cif file (e.g. D(calc), F000 and Mol.Wght). In the refinement, commands DFIX, SADI and ISOR were used to restrain some bond lengths and thermal factors. ; _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^)+(0.1800P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7859 _refine_ls_number_parameters 681 _refine_ls_number_restraints 66 _refine_ls_R_factor_all 0.1487 _refine_ls_R_factor_gt 0.0961 _refine_ls_wR_factor_ref 0.2927 _refine_ls_wR_factor_gt 0.2676 _refine_ls_goodness_of_fit_ref 0.957 _refine_ls_restrained_S_all 1.007 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.49378(16) 0.53414(16) 0.3266(3) 0.0513(12) Uani 1 1 d . . . C2 C 0.46093(15) 0.57333(16) 0.2869(3) 0.0538(13) Uani 1 1 d . . . H2A H 0.4628 0.5934 0.3263 0.065 Uiso 1 1 calc R . . H2B H 0.4369 0.5475 0.3000 0.065 Uiso 1 1 calc R . . C3 C 0.42018(15) 0.56620(14) 0.1645(3) 0.0474(12) Uani 1 1 d . . . C4 C 0.38449(14) 0.58290(16) 0.0585(3) 0.0492(12) Uani 1 1 d . . . H4A H 0.3795 0.6054 0.0659 0.059 Uiso 1 1 calc R . . H4B H 0.3615 0.5587 0.0814 0.059 Uiso 1 1 calc R . . C5 C 0.36337(14) 0.53877(15) -0.0644(3) 0.0430(11) Uani 1 1 d . . . C6 C 0.34089(14) 0.51244(16) -0.2038(3) 0.0521(13) Uani 1 1 d . . . H6A H 0.3187 0.4912 -0.1724 0.063 Uiso 1 1 calc R . . H6B H 0.3292 0.5239 -0.2408 0.063 Uiso 1 1 calc R . . C7 C 0.35561(15) 0.45757(17) -0.2330(3) 0.0526(13) Uani 1 1 d . . . C8 C 0.45526(17) 0.53989(17) -0.3312(3) 0.0542(13) Uani 1 1 d . . . C9 C 0.43315(16) 0.58844(15) -0.2933(3) 0.0510(12) Uani 1 1 d . . . H9A H 0.4141 0.5923 -0.3266 0.061 Uiso 1 1 calc R . . H9B H 0.4604 0.6071 -0.3131 0.061 Uiso 1 1 calc R . . C10 C 0.46225(16) 0.62560(15) -0.1642(3) 0.0487(12) Uani 1 1 d . . . C11 C 0.47468(16) 0.66144(14) -0.0327(3) 0.0521(13) Uani 1 1 d . . . H11A H 0.5005 0.6796 -0.0589 0.063 Uiso 1 1 calc R . . H11B H 0.4621 0.6774 -0.0180 0.063 Uiso 1 1 calc R . . C12 C 0.51983(15) 0.65176(13) 0.0629(3) 0.0468(12) Uani 1 1 d . . . C13 C 0.55555(15) 0.65440(15) 0.1898(3) 0.0567(13) Uani 1 1 d . . . H13A H 0.5790 0.6690 0.1542 0.068 Uiso 1 1 calc R . . H13B H 0.5564 0.6735 0.2304 0.068 Uiso 1 1 calc R . . C14 C 0.59245(16) 0.61911(16) 0.2216(3) 0.0553(13) Uani 1 1 d . . . C15 C 0.56177(16) 0.58468(16) 0.3422(3) 0.0551(13) Uani 1 1 d . . . H15 H 0.5737 0.5966 0.3954 0.066 Uiso 1 1 calc R . . C16 C 0.53725(15) 0.60411(15) 0.3056(3) 0.0501(12) Uani 1 1 d . . . H16 H 0.5369 0.6243 0.3427 0.060 Uiso 1 1 calc R . . C17 C 0.47990(14) 0.62847(14) 0.1800(3) 0.0423(11) Uani 1 1 d . . . H17 H 0.4833 0.6468 0.2254 0.051 Uiso 1 1 calc R . . C18 C 0.45492(14) 0.63238(14) 0.1099(3) 0.0448(11) Uani 1 1 d . . . H18 H 0.4463 0.6522 0.1229 0.054 Uiso 1 1 calc R . . C19 C 0.40406(14) 0.60869(14) -0.0874(3) 0.0453(11) Uani 1 1 d . . . H19 H 0.3937 0.6276 -0.0810 0.054 Uiso 1 1 calc R . . C20 C 0.39180(14) 0.58686(15) -0.1699(3) 0.0492(12) Uani 1 1 d . . . H20 H 0.3753 0.5953 -0.2018 0.059 Uiso 1 1 calc R . . C21 C 0.38542(15) 0.51319(15) -0.3227(3) 0.0513(13) Uani 1 1 d . . . H21 H 0.3715 0.5201 -0.3648 0.062 Uiso 1 1 calc R . . C22 C 0.39436(15) 0.48035(15) -0.3523(3) 0.0495(12) Uani 1 1 d . . . H22 H 0.3818 0.4695 -0.4057 0.059 Uiso 1 1 calc R . . C23 C 0.53867(18) 0.51504(17) 0.3986(3) 0.0598(14) Uani 1 1 d . . . H23A H 0.5125 0.4925 0.4156 0.072 Uiso 1 1 calc R . . H23B H 0.5533 0.5294 0.4476 0.072 Uiso 1 1 calc R . . C24 C 0.62862(16) 0.59095(15) 0.2985(4) 0.0591(14) Uani 1 1 d . . . H24A H 0.6506 0.6093 0.2626 0.071 Uiso 1 1 calc R . . H24B H 0.6371 0.5999 0.3543 0.071 Uiso 1 1 calc R . . N1 N 0.53184(13) 0.54197(13) 0.3491(2) 0.0521(10) Uani 1 1 d . . . N2 N 0.49658(12) 0.56890(12) 0.2942(2) 0.0508(10) Uani 1 1 d . . . N3 N 0.45647(11) 0.58598(11) 0.2050(2) 0.0453(10) Uani 1 1 d . . . N4 N 0.42025(11) 0.59135(11) 0.1029(2) 0.0456(10) Uani 1 1 d . . . N5 N 0.38664(11) 0.57657(12) -0.0284(2) 0.0466(10) Uani 1 1 d . . . N6 N 0.36848(11) 0.54423(12) -0.1479(2) 0.0477(10) Uani 1 1 d . . . N7 N 0.35949(12) 0.49449(13) -0.2513(2) 0.0528(11) Uani 1 1 d . . . N8 N 0.37721(13) 0.44919(13) -0.2893(3) 0.0550(11) Uani 1 1 d . . . N9 N 0.43811(13) 0.50134(14) -0.3573(3) 0.0563(11) Uani 1 1 d . . . N10 N 0.42507(12) 0.54742(12) -0.3038(2) 0.0498(10) Uani 1 1 d . . . N11 N 0.42992(12) 0.59882(12) -0.2094(2) 0.0518(11) Uani 1 1 d . . . N12 N 0.44857(11) 0.63028(12) -0.0910(2) 0.0470(10) Uani 1 1 d . . . N13 N 0.48244(12) 0.64541(11) 0.0413(2) 0.0450(10) Uani 1 1 d . . . N14 N 0.51871(11) 0.63956(11) 0.1418(2) 0.0453(10) Uani 1 1 d . . . N15 N 0.55847(12) 0.62241(13) 0.2305(2) 0.0550(11) Uani 1 1 d . . . N16 N 0.59318(12) 0.59407(13) 0.2806(3) 0.0542(11) Uani 1 1 d . . . O1 O 0.46253(12) 0.50155(11) 0.3347(2) 0.0671(11) Uani 1 1 d . . . O2 O 0.39307(11) 0.53148(11) 0.1775(2) 0.0612(10) Uani 1 1 d . . . O3 O 0.34300(10) 0.50689(11) -0.0297(2) 0.0589(9) Uani 1 1 d . . . O4 O 0.33560(11) 0.43516(12) -0.1773(2) 0.0668(10) Uani 1 1 d . . . O5 O 0.49191(12) 0.56493(12) -0.3297(2) 0.0692(11) Uani 1 1 d . . . O6 O 0.49828(11) 0.64285(11) -0.1862(2) 0.0647(10) Uani 1 1 d . . . O7 O 0.55028(11) 0.66631(11) 0.0187(2) 0.0642(10) Uani 1 1 d . . . O8 O 0.61799(12) 0.63518(12) 0.1671(2) 0.0715(11) Uani 1 1 d . . . C1S C 0.4574(3) 0.5067(4) -0.0461(7) 0.065(3) Uani 0.50 1 d PD A 1 C2S C 0.4244(4) 0.4910(5) 0.0192(8) 0.108(5) Uani 0.50 1 d PD A 1 C3S C 0.4618(6) 0.4585(6) 0.0818(9) 0.122(8) Uani 0.50 1 d PD A 1 C4S C 0.4899(5) 0.4659(6) 0.1577(8) 0.121(7) Uani 0.50 1 d PD . 1 C5S C 0.4240(5) 0.4775(6) 0.1741(8) 0.130(6) Uani 0.50 1 d PD A 1 N2S N 0.4432(6) 0.4839(7) 0.0934(9) 0.208(9) Uani 0.50 1 d PDU A 1 N1S N 0.4664(6) 0.5139(15) -0.1305(9) 0.34(3) Uani 0.50 1 d PDU . 1 C1S' C 0.4204(6) 0.4603(7) -0.0486(15) 0.192(10) Uani 0.50 1 d PDU B 2 C2S' C 0.4478(7) 0.4894(5) -0.1183(11) 0.165(9) Uani 0.50 1 d PD B 2 C3S' C 0.5171(5) 0.5601(6) -0.1085(13) 0.166(10) Uani 0.50 1 d PD B 2 C4S' C 0.5506(8) 0.5502(11) -0.0783(14) 0.26(3) Uani 0.50 1 d PDU . 2 C5S' C 0.4594(6) 0.5452(6) -0.0348(12) 0.140(7) Uani 0.50 1 d PD B 2 N1S' N 0.4392(6) 0.4384(6) -0.0083(12) 0.213(9) Uani 0.50 1 d PDU . 2 N2S' N 0.4797(4) 0.5254(5) -0.0746(9) 0.126(5) Uani 0.50 1 d PDU B 2 O1W O 0.24651(15) 0.06146(14) 0.2267(3) 0.1074(17) Uani 1 1 d . . . H1WA H 0.2369 0.0409 0.2583 0.129 Uiso 1 1 d R . . H1WB H 0.2723 0.0733 0.2295 0.129 Uiso 1 1 d R . . O2W O 0.26015(18) 0.17718(19) 0.1772(3) 0.124(2) Uani 1 1 d . . . H2WA H 0.2471 0.1520 0.1652 0.149 Uiso 1 1 d R . . H2WB H 0.2412 0.1871 0.1892 0.149 Uiso 1 1 d R . . O3W O 0.2001(2) 0.0938(2) 0.1645(3) 0.135(2) Uani 1 1 d . . . H3WA H 0.2129 0.0814 0.1812 0.162 Uiso 1 1 d R . . H3WB H 0.1790 0.0760 0.1399 0.162 Uiso 1 1 d R . . O4W O 0.4359(2) 0.3617(2) 0.2475(7) 0.223(5) Uani 1 1 d . . . H4WA H 0.4458 0.3848 0.2709 0.268 Uiso 1 1 d R . . H4WB H 0.4557 0.3598 0.2281 0.268 Uiso 1 1 d R . . O5W O 0.07441(15) 0.08393(15) 0.9556(3) 0.1015(16) Uani 1 1 d . . . H5WA H 0.1004 0.0839 0.9556 0.122 Uiso 1 1 d R . . H5WB H 0.0780 0.1084 0.9272 0.122 Uiso 1 1 d R . . O6W O 0.3526(6) 0.3066(8) 0.1517(10) 0.234(10) Uani 0.50 1 d P . . H6WA H 0.3786 0.3066 0.1518 0.281 Uiso 0.50 1 d PR . . H6WB H 0.3563 0.3310 0.1234 0.281 Uiso 0.50 1 d PR . . O7W O 0.3212(4) 0.2401(3) 0.0504(15) 0.243(12) Uani 0.50 1 d P . . H7WB H 0.3248 0.2646 0.0221 0.291 Uiso 0.50 1 d PR . . H7WC H 0.3125 0.2401 0.1071 0.291 Uiso 0.50 1 d PR . . O8W O 0.3654(4) 0.3205(5) 0.0075(13) 0.205(8) Uani 0.50 1 d P . . H8WA H 0.3913 0.3205 0.0075 0.246 Uiso 0.50 1 d PR . . H8WB H 0.3690 0.3450 -0.0209 0.246 Uiso 0.50 1 d PR . . O9W O 0.3906(6) 0.3857(13) 0.169(2) 0.23(2) Uani 0.25 1 d P . . H9WB H 0.3942 0.4101 0.1397 0.278 Uiso 0.25 1 d PR . . H9WA H 0.3694 0.3610 0.1414 0.278 Uiso 0.25 1 d PR . . O10W O 0.2774(3) 0.2887(3) 0.2962(5) 0.157(4) Uani 0.75 1 d P . . H102 H 0.2809 0.3131 0.2679 0.189 Uiso 0.75 1 d PR . . H101 H 0.2565 0.2642 0.2680 0.189 Uiso 0.75 1 d PR . . O11W O 0.4923(6) 0.4532(5) 0.8972(9) 0.182(7) Uani 0.50 1 d P . . H111 H 0.5183 0.4532 0.8973 0.218 Uiso 0.50 1 d PR . . H112 H 0.4959 0.4777 0.8689 0.218 Uiso 0.50 1 d PR . . Cl1 Cl 0.04543(7) 0.09310(12) 0.6011(2) 0.1751(15) Uani 1 1 d . . . Cl2 Cl 0.04652(9) 0.10159(11) 0.8005(2) 0.1643(12) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.052(3) 0.051(3) 0.051(3) 0.005(2) 0.008(2) 0.026(3) C2 0.055(3) 0.060(3) 0.049(3) 0.012(2) 0.009(2) 0.030(3) C3 0.047(3) 0.040(3) 0.050(3) 0.002(2) 0.013(2) 0.018(2) C4 0.043(3) 0.054(3) 0.045(3) -0.002(2) 0.011(2) 0.020(2) C5 0.035(2) 0.050(3) 0.043(3) 0.011(2) 0.007(2) 0.021(2) C6 0.038(3) 0.063(3) 0.049(3) 0.001(2) 0.002(2) 0.020(2) C7 0.048(3) 0.061(3) 0.045(3) 0.008(3) -0.003(2) 0.024(3) C8 0.057(4) 0.058(3) 0.045(3) 0.011(2) 0.004(2) 0.027(3) C9 0.058(3) 0.052(3) 0.041(3) 0.011(2) 0.006(2) 0.026(3) C10 0.051(3) 0.046(3) 0.047(3) 0.009(2) 0.003(2) 0.023(3) C11 0.059(3) 0.036(3) 0.052(3) 0.008(2) 0.003(2) 0.016(2) C12 0.055(3) 0.033(2) 0.047(3) 0.001(2) 0.011(3) 0.019(2) C13 0.051(3) 0.046(3) 0.063(3) 0.010(3) 0.006(3) 0.016(2) C14 0.049(3) 0.057(3) 0.055(3) 0.000(3) 0.002(3) 0.023(3) C15 0.056(3) 0.066(3) 0.046(3) 0.002(2) 0.005(2) 0.033(3) C16 0.051(3) 0.053(3) 0.046(3) 0.002(2) 0.001(2) 0.026(3) C17 0.048(3) 0.042(3) 0.035(2) -0.003(2) 0.001(2) 0.021(2) C18 0.047(3) 0.038(3) 0.049(3) -0.001(2) 0.009(2) 0.021(2) C19 0.047(3) 0.046(3) 0.051(3) 0.006(2) 0.001(2) 0.028(2) C20 0.045(3) 0.059(3) 0.045(3) 0.010(2) 0.003(2) 0.028(3) C21 0.052(3) 0.061(3) 0.040(3) -0.001(2) -0.005(2) 0.028(3) C22 0.052(3) 0.059(3) 0.040(3) 0.002(2) -0.002(2) 0.030(3) C23 0.072(4) 0.063(3) 0.051(3) 0.015(3) 0.016(3) 0.038(3) C24 0.051(3) 0.049(3) 0.075(4) 0.003(3) 0.003(3) 0.023(3) N1 0.055(3) 0.055(3) 0.051(2) 0.006(2) 0.004(2) 0.032(2) N2 0.043(2) 0.051(2) 0.055(3) 0.011(2) 0.0059(19) 0.021(2) N3 0.042(2) 0.040(2) 0.047(2) 0.0054(18) 0.0001(18) 0.0155(19) N4 0.041(2) 0.044(2) 0.043(2) -0.0008(18) 0.0017(18) 0.0149(19) N5 0.046(2) 0.048(2) 0.040(2) 0.0003(18) 0.0067(18) 0.020(2) N6 0.042(2) 0.054(3) 0.040(2) -0.0004(19) -0.0049(18) 0.019(2) N7 0.053(3) 0.053(3) 0.048(2) 0.004(2) 0.007(2) 0.023(2) N8 0.060(3) 0.054(3) 0.050(2) 0.005(2) 0.007(2) 0.027(2) N9 0.057(3) 0.063(3) 0.053(3) 0.009(2) 0.007(2) 0.033(2) N10 0.046(2) 0.057(3) 0.044(2) 0.0073(19) 0.0028(18) 0.024(2) N11 0.048(2) 0.054(3) 0.044(2) 0.0035(19) 0.0064(19) 0.018(2) N12 0.044(2) 0.049(2) 0.043(2) 0.0054(19) 0.0037(18) 0.020(2) N13 0.044(2) 0.043(2) 0.039(2) 0.0055(17) 0.0019(18) 0.0152(19) N14 0.043(2) 0.044(2) 0.045(2) 0.0033(18) 0.0014(18) 0.0191(18) N15 0.050(3) 0.063(3) 0.051(3) 0.009(2) 0.000(2) 0.027(2) N16 0.045(2) 0.061(3) 0.055(3) 0.011(2) 0.003(2) 0.025(2) O1 0.059(2) 0.053(2) 0.085(3) 0.0166(19) 0.010(2) 0.025(2) O2 0.050(2) 0.051(2) 0.066(2) 0.0080(18) 0.0061(17) 0.0128(18) O3 0.055(2) 0.055(2) 0.052(2) 0.0073(18) 0.0100(17) 0.0164(18) O4 0.061(2) 0.071(2) 0.065(2) 0.017(2) 0.0139(19) 0.030(2) O5 0.051(2) 0.075(3) 0.075(3) 0.005(2) 0.0055(19) 0.026(2) O6 0.047(2) 0.069(2) 0.067(2) 0.0049(19) 0.0097(18) 0.0203(19) O7 0.054(2) 0.068(2) 0.064(2) 0.0203(19) 0.0169(19) 0.0264(19) O8 0.061(2) 0.080(3) 0.069(2) 0.023(2) 0.020(2) 0.032(2) C1S 0.049(7) 0.065(7) 0.064(8) 0.031(6) -0.012(6) 0.016(6) C2S 0.090(11) 0.139(14) 0.104(12) 0.023(11) 0.013(9) 0.065(11) C3S 0.098(12) 0.122(15) 0.137(18) 0.051(13) -0.022(11) 0.049(12) C4S 0.131(16) 0.126(16) 0.083(12) -0.008(10) -0.009(11) 0.048(13) C5S 0.138(15) 0.134(15) 0.129(15) -0.051(12) -0.040(13) 0.077(13) N2S 0.182(12) 0.208(12) 0.233(13) 0.057(10) 0.000(9) 0.096(9) N1S 0.34(3) 0.34(3) 0.33(3) 0.007(11) -0.015(11) 0.167(16) C1S' 0.186(14) 0.187(13) 0.216(14) 0.006(10) -0.028(10) 0.102(10) C2S' 0.18(2) 0.15(2) 0.14(2) -0.019(16) -0.018(18) 0.067(19) C3S' 0.15(2) 0.16(2) 0.17(2) 0.065(19) -0.030(17) 0.069(18) C4S' 0.24(3) 0.27(3) 0.26(3) 0.002(11) -0.001(11) 0.118(16) C5S' 0.160(18) 0.137(17) 0.174(19) -0.021(14) 0.002(15) 0.113(15) N1S' 0.178(12) 0.240(13) 0.177(12) 0.060(9) -0.028(9) 0.072(9) N2S' 0.114(9) 0.154(10) 0.104(8) 0.025(8) -0.039(7) 0.063(7) O1W 0.100(4) 0.084(3) 0.094(3) 0.018(3) 0.010(3) 0.013(3) O2W 0.134(5) 0.148(5) 0.120(4) -0.054(4) -0.032(4) 0.094(4) O3W 0.162(6) 0.134(5) 0.100(4) 0.011(3) 0.011(4) 0.066(4) O4W 0.144(6) 0.129(6) 0.391(15) 0.074(7) 0.128(8) 0.064(5) O5W 0.097(3) 0.097(3) 0.146(4) -0.024(3) 0.016(3) 0.075(3) O6W 0.206(17) 0.47(3) 0.167(13) 0.022(17) -0.006(12) 0.28(2) O7W 0.096(9) 0.062(7) 0.55(4) -0.077(13) 0.012(14) 0.027(6) O8W 0.112(10) 0.139(12) 0.31(2) 0.062(13) 0.067(12) 0.025(9) O9W 0.043(12) 0.35(5) 0.25(3) 0.16(4) 0.039(17) 0.06(2) O10W 0.244(11) 0.122(6) 0.122(6) 0.015(5) -0.060(7) 0.103(7) O11W 0.29(2) 0.182(14) 0.156(12) -0.099(10) -0.086(12) 0.176(15) Cl1 0.0679(13) 0.256(4) 0.186(3) 0.084(3) 0.0025(14) 0.0700(18) Cl2 0.136(2) 0.210(3) 0.182(3) 0.042(2) 0.0661(19) 0.112(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.218(6) . ? C1 N1 1.369(6) . ? C1 N2 1.373(6) . ? C2 N2 1.447(6) . ? C2 N3 1.460(6) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 O2 1.216(5) . ? C3 N3 1.364(6) . ? C3 N4 1.385(6) . ? C4 N4 1.425(6) . ? C4 N5 1.449(6) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 O3 1.201(5) . ? C5 N6 1.379(6) . ? C5 N5 1.382(6) . ? C6 N7 1.429(6) . ? C6 N6 1.456(6) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 O4 1.217(6) . ? C7 N7 1.364(7) . ? C7 N8 1.370(6) . ? C8 O5 1.229(6) . ? C8 N9 1.337(7) . ? C8 N10 1.384(7) . ? C9 N10 1.436(6) . ? C9 N11 1.449(6) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 O6 1.236(6) . ? C10 N12 1.350(6) . ? C10 N11 1.353(6) . ? C11 N13 1.448(6) . ? C11 N12 1.453(6) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 O7 1.233(6) . ? C12 N13 1.359(6) . ? C12 N14 1.363(6) . ? C13 N15 1.434(6) . ? C13 N14 1.447(6) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 O8 1.229(6) . ? C14 N15 1.362(6) . ? C14 N16 1.363(7) . ? C15 N1 1.443(6) . ? C15 N16 1.459(6) . ? C15 C16 1.564(7) . ? C15 H15 0.9800 . ? C16 N15 1.440(6) . ? C16 N2 1.461(6) . ? C16 H16 0.9800 . ? C17 N14 1.452(6) . ? C17 N3 1.455(6) . ? C17 C18 1.540(7) . ? C17 H17 0.9800 . ? C18 N13 1.439(6) . ? C18 N4 1.454(6) . ? C18 H18 0.9800 . ? C19 N5 1.429(6) . ? C19 N12 1.462(6) . ? C19 C20 1.527(7) . ? C19 H19 0.9800 . ? C20 N11 1.432(6) . ? C20 N6 1.446(6) . ? C20 H20 0.9800 . ? C21 N10 1.444(6) . ? C21 N7 1.460(6) . ? C21 C22 1.523(7) . ? C21 H21 0.9800 . ? C22 N9 1.438(6) . ? C22 N8 1.452(6) . ? C22 H22 0.9800 . ? C23 N1 1.423(6) . ? C23 N9 1.471(7) 10_665 ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 N8 1.431(6) 10_665 ? C24 N16 1.436(6) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? N8 C24 1.431(6) 10_665 ? N9 C23 1.471(7) 10_665 ? C1S N1S 1.414(10) . ? C1S C2S 1.520(9) . ? C2S N2S 1.497(9) . ? C3S N2S 1.464(10) . ? C3S C4S 1.564(10) . ? C4S N1S 1.504(10) 10_665 ? C5S N2S 1.466(10) . ? N1S C4S 1.504(10) 10_665 ? C1S' N1S' 1.491(10) . ? C1S' C2S' 1.564(10) . ? C2S' N2S' 1.476(10) . ? C3S' N2S' 1.478(10) . ? C3S' C4S' 1.570(10) . ? C4S' N1S' 1.473(11) 10_665 ? C5S' N2S' 1.465(10) . ? N1S' C4S' 1.473(11) 10_665 ? O1W H1WA 0.8500 . ? O1W H1WB 0.8499 . ? O2W H2WA 0.8499 . ? O2W H2WB 0.9842 . ? O3W H3WB 0.8464 . ? O3W H3WA 0.8724 . ? O3W H3WB 0.8464 . ? O4W H4WA 0.8502 . ? O4W H4WB 0.8497 . ? O5W H5WA 0.9829 . ? O5W H5WB 0.9829 . ? O6W H6WA 0.9837 . ? O6W H6WB 0.9828 . ? O7W H7WB 0.9833 . ? O7W H7WC 0.9826 . ? O8W H8WA 0.9817 . ? O8W H8WB 0.9844 . ? O9W H9WB 0.9852 . ? O9W H9WA 0.9818 . ? O10W H102 0.9824 . ? O10W H101 0.9827 . ? O11W H111 0.9837 . ? O11W H112 0.9830 . ? 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 O1 C1 N1 125.1(5) . . ? O1 C1 N2 125.8(5) . . ? N1 C1 N2 109.1(4) . . ? N2 C2 N3 112.4(4) . . ? N2 C2 H2A 109.1 . . ? N3 C2 H2A 109.1 . . ? N2 C2 H2B 109.1 . . ? N3 C2 H2B 109.1 . . ? H2A C2 H2B 107.8 . . ? O2 C3 N3 125.8(5) . . ? O2 C3 N4 125.5(5) . . ? N3 C3 N4 108.6(4) . . ? N4 C4 N5 114.3(4) . . ? N4 C4 H4A 108.7 . . ? N5 C4 H4A 108.7 . . ? N4 C4 H4B 108.7 . . ? N5 C4 H4B 108.7 . . ? H4A C4 H4B 107.6 . . ? O3 C5 N6 126.0(5) . . ? O3 C5 N5 126.8(4) . . ? N6 C5 N5 107.2(4) . . ? N7 C6 N6 114.4(4) . . ? N7 C6 H6A 108.7 . . ? N6 C6 H6A 108.7 . . ? N7 C6 H6B 108.7 . . ? N6 C6 H6B 108.7 . . ? H6A C6 H6B 107.6 . . ? O4 C7 N7 126.1(5) . . ? O4 C7 N8 125.2(5) . . ? N7 C7 N8 108.7(4) . . ? O5 C8 N9 126.4(5) . . ? O5 C8 N10 124.4(5) . . ? N9 C8 N10 109.1(5) . . ? N10 C9 N11 114.0(4) . . ? N10 C9 H9A 108.8 . . ? N11 C9 H9A 108.8 . . ? N10 C9 H9B 108.8 . . ? N11 C9 H9B 108.8 . . ? H9A C9 H9B 107.7 . . ? O6 C10 N12 125.7(5) . . ? O6 C10 N11 125.7(5) . . ? N12 C10 N11 108.6(4) . . ? N13 C11 N12 113.9(4) . . ? N13 C11 H11A 108.8 . . ? N12 C11 H11A 108.8 . . ? N13 C11 H11B 108.8 . . ? N12 C11 H11B 108.8 . . ? H11A C11 H11B 107.7 . . ? O7 C12 N13 125.8(5) . . ? O7 C12 N14 124.7(5) . . ? N13 C12 N14 109.4(4) . . ? N15 C13 N14 112.9(4) . . ? N15 C13 H13A 109.0 . . ? N14 C13 H13A 109.0 . . ? N15 C13 H13B 109.0 . . ? N14 C13 H13B 109.0 . . ? H13A C13 H13B 107.8 . . ? O8 C14 N15 125.3(5) . . ? O8 C14 N16 124.9(5) . . ? N15 C14 N16 109.7(4) . . ? N1 C15 N16 114.5(4) . . ? N1 C15 C16 103.9(4) . . ? N16 C15 C16 103.1(4) . . ? N1 C15 H15 111.6 . . ? N16 C15 H15 111.6 . . ? C16 C15 H15 111.6 . . ? N15 C16 N2 114.3(4) . . ? N15 C16 C15 103.4(4) . . ? N2 C16 C15 102.8(4) . . ? N15 C16 H16 111.9 . . ? N2 C16 H16 111.9 . . ? C15 C16 H16 111.9 . . ? N14 C17 N3 114.2(4) . . ? N14 C17 C18 103.5(3) . . ? N3 C17 C18 104.5(4) . . ? N14 C17 H17 111.4 . . ? N3 C17 H17 111.4 . . ? C18 C17 H17 111.4 . . ? N13 C18 N4 114.7(4) . . ? N13 C18 C17 103.8(4) . . ? N4 C18 C17 103.0(4) . . ? N13 C18 H18 111.6 . . ? N4 C18 H18 111.6 . . ? C17 C18 H18 111.6 . . ? N5 C19 N12 114.5(4) . . ? N5 C19 C20 104.4(4) . . ? N12 C19 C20 102.8(4) . . ? N5 C19 H19 111.5 . . ? N12 C19 H19 111.5 . . ? C20 C19 H19 111.5 . . ? N11 C20 N6 114.9(4) . . ? N11 C20 C19 103.9(4) . . ? N6 C20 C19 103.6(4) . . ? N11 C20 H20 111.3 . . ? N6 C20 H20 111.3 . . ? C19 C20 H20 111.3 . . ? N10 C21 N7 114.2(4) . . ? N10 C21 C22 104.2(4) . . ? N7 C21 C22 103.2(4) . . ? N10 C21 H21 111.6 . . ? N7 C21 H21 111.6 . . ? C22 C21 H21 111.6 . . ? N9 C22 N8 114.4(4) . . ? N9 C22 C21 103.4(4) . . ? N8 C22 C21 104.3(4) . . ? N9 C22 H22 111.4 . . ? N8 C22 H22 111.4 . . ? C21 C22 H22 111.4 . . ? N1 C23 N9 113.7(4) . 10_665 ? N1 C23 H23A 108.8 . . ? N9 C23 H23A 108.8 10_665 . ? N1 C23 H23B 108.8 . . ? N9 C23 H23B 108.8 10_665 . ? H23A C23 H23B 107.7 . . ? N8 C24 N16 114.4(4) 10_665 . ? N8 C24 H24A 108.7 10_665 . ? N16 C24 H24A 108.7 . . ? N8 C24 H24B 108.7 10_665 . ? N16 C24 H24B 108.7 . . ? H24A C24 H24B 107.6 . . ? C1 N1 C23 123.1(4) . . ? C1 N1 C15 111.9(4) . . ? C23 N1 C15 121.7(4) . . ? C1 N2 C2 120.9(4) . . ? C1 N2 C16 111.5(4) . . ? C2 N2 C16 121.6(4) . . ? C3 N3 C17 111.2(4) . . ? C3 N3 C2 121.0(4) . . ? C17 N3 C2 120.9(4) . . ? C3 N4 C4 122.8(4) . . ? C3 N4 C18 111.6(4) . . ? C4 N4 C18 122.0(4) . . ? C5 N5 C19 112.3(4) . . ? C5 N5 C4 121.9(4) . . ? C19 N5 C4 124.1(4) . . ? C5 N6 C20 112.1(4) . . ? C5 N6 C6 120.6(4) . . ? C20 N6 C6 123.5(4) . . ? C7 N7 C6 122.9(4) . . ? C7 N7 C21 112.0(4) . . ? C6 N7 C21 125.1(4) . . ? C7 N8 C24 121.6(4) . 10_665 ? C7 N8 C22 111.4(4) . . ? C24 N8 C22 123.9(4) 10_665 . ? C8 N9 C22 112.5(4) . . ? C8 N9 C23 122.8(5) . 10_665 ? C22 N9 C23 124.0(4) . 10_665 ? C8 N10 C9 120.7(4) . . ? C8 N10 C21 110.0(4) . . ? C9 N10 C21 124.1(4) . . ? C10 N11 C20 112.5(4) . . ? C10 N11 C9 123.5(4) . . ? C20 N11 C9 123.3(4) . . ? C10 N12 C11 122.5(4) . . ? C10 N12 C19 111.9(4) . . ? C11 N12 C19 123.7(4) . . ? C12 N13 C18 111.7(4) . . ? C12 N13 C11 123.7(4) . . ? C18 N13 C11 122.0(4) . . ? C12 N14 C13 121.4(4) . . ? C12 N14 C17 111.1(4) . . ? C13 N14 C17 121.3(4) . . ? C14 N15 C13 120.2(4) . . ? C14 N15 C16 111.9(4) . . ? C13 N15 C16 122.8(4) . . ? C14 N16 C24 123.1(4) . . ? C14 N16 C15 111.1(4) . . ? C24 N16 C15 121.5(4) . . ? C1 O1 C5S 107.4(5) . . ? N1S C1S C2S 146.3(11) . . ? N2S C2S C1S 105.6(9) . . ? N2S C3S C4S 106.8(11) . . ? N1S C4S C3S 109.5(11) 10_665 . ? N2S C5S O1 128.9(12) . . ? C3S N2S C5S 111.7(11) . . ? C3S N2S C2S 116.3(12) . . ? C5S N2S C2S 121.2(12) . . ? C1S N1S C4S 118.9(13) . 10_665 ? N1S' C1S' C2S' 112.4(14) . . ? N2S' C2S' C1S' 104.3(12) . . ? N2S' C3S' C4S' 101.6(13) . . ? N1S' C4S' C3S' 110.8(14) 10_665 . ? N2S' C5S' O3 127.2(10) . . ? C4S' N1S' C1S' 112.9(15) 10_665 . ? C5S' N2S' C2S' 106.9(11) . . ? C5S' N2S' C3S' 103.1(12) . . ? C2S' N2S' C3S' 128.2(13) . . ? H1WA O1W H1WB 107.7 . . ? O7W O2W H2WA 119.8 . . ? O7W O2W H2WB 104.0 . . ? H2WA O2W H2WB 110.6 . . ? H3WB O3W H3WA 106.0 . . ? O2W O3W H3WA 103.1 . . ? H3WA O3W H3WB 106.0 . . ? H4WA O4W H4WB 107.7 . . ? H5WA O5W H5WB 109.5 . . ? O5W O6W H6WA 112.8 . . ? O5W O6W H6WB 128.0 . . ? H6WA O6W H6WB 109.4 . . ? O2W O7W H7WB 137.0 . . ? O8W O7W H7WC 105.2 . . ? H7WB O7W H7WC 109.4 . . ? O6W O8W O7W 64.0(8) . . ? H8WA O8W H8WB 109.5 . . ? H9WB O9W H9WA 109.9 . . ? H102 O10W H101 109.6 . . ? H111 O11W H112 109.4 . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.883 _refine_diff_density_min -0.398 _refine_diff_density_rms 0.106 # start Validation Reply Form _vrf_PLAT242_I ; PROBLEM: Check Low Ueq as Compared to Neighbors for C1S RESPONSE: This is resulted from the disorder of its adjacent atoms. ; _vrf_PLAT432_I ; PROBLEM: Short Inter X...Y Contact O11W .. C2S' .. 2.66 Ang. RESPONSE: This is resulted from the disorder of the tetra-azacyclododecane and water O11W molecules. ; _vrf_PLAT601_I ; PROBLEM: Structure Contains Solvent Accessible VOIDS of . 169.00 A**3. RESPONSE: Owing to the weak diffraction of the crystal selected for experiment, some water solvent molecules could not be properly modeled which resulted in the void of 169.0A^3^ in the crystal structure. ; _vrf_DENSD01_I ; PROBLEM: The ratio of the submitted crystal density and that calculated from the formula is outside the range 0.95 <> 1.05 Crystal density given = 1.524 Calculated crystal density = 1.445 RESPONSE: Although the tetra-azacyclododecane hydrogen atoms were not added in the refinement, the contributions of these H atoms (left out of the refined model) should be included in the reported formula, formula weight, etc., data in the CIF and text which led to the alert. ; _vrf_PLAT220_I ; PROBLEM: Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.01 Ratio RESPONSE: This should be resulted from the disorder of the tetra-azacyclododecane carbon atoms. ; _vrf_PLAT046_I ; PROBLEM: Reported Z, MW and D(calc) are Inconsistent .... 1.45 RESPONSE: Although the tetra-azacyclododecane hydrogen atoms were not included in the refinement, the contributions of these H atoms (left out of the refined model) in the reported formula, formula weight, etc., data in the CIF and text which lead to the alert. ; # end Validation Reply Form