Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Gokel, G.' 'Barbour, Leonard J.' 'Hu, Jun' _publ_contact_author_name 'Prof G Gokel' _publ_contact_author_address ; Molecular Biol. Pharm. Washington University Medical School, Box 8103 St Louis MO 63110 USA ; _publ_contact_author_email '?' _publ_requested_journal 'Chemical Communications' _publ_section_title ; Calcium Cation Complexation by Lariat Ether Receptors having Arene-terminated Sidearms ; data_e:\_georg~1\jxh\jx19ef~1\sad _database_code_CSD 189368 _audit_creation_method SHELXL-97 _chemical_name_systematic ; N-2-((3-indolyl)ethyl)aza-15-crown-5.calcium diiodide ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H40 Ca I2 N2 O9' _chemical_formula_weight 746.42 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Ca' 'Ca' 0.2262 0.3064 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'I' 'I' -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.8848(12) _cell_length_b 12.7563(16) _cell_length_c 12.3719(16) _cell_angle_alpha 90.00 _cell_angle_beta 110.326(2) _cell_angle_gamma 90.00 _cell_volume 1462.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.695 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 2.370 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.5887 _exptl_absorpt_correction_T_max 0.6486 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 9284 _diffrn_reflns_av_R_equivalents 0.0208 _diffrn_reflns_av_sigmaI/netI 0.0294 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 27.12 _reflns_number_total 6240 _reflns_number_gt 5986 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0395P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.026(14) _refine_ls_number_reflns 6240 _refine_ls_number_parameters 347 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0279 _refine_ls_R_factor_gt 0.0262 _refine_ls_wR_factor_ref 0.0633 _refine_ls_wR_factor_gt 0.0624 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.007 _refine_ls_shift/su_max 0.210 _refine_ls_shift/su_mean 0.008 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 I1 I 0.73781(3) 0.098453(18) 0.27422(2) 0.03876(7) Uani 1 1 d . . . I2 I 0.98308(2) -0.224744(18) 0.00511(2) 0.03564(7) Uani 1 1 d . . . Ca1 Ca 1.29976(7) -0.00022(5) -0.16044(5) 0.02164(13) Uani 1 1 d . . . O24 O 1.3420(2) -0.0807(2) -0.3263(2) 0.0277(5) Uani 1 1 d . . . O21 O 1.5560(2) -0.0660(2) -0.1236(2) 0.0306(5) Uani 1 1 d . . . O18 O 1.4808(3) 0.1393(2) -0.1412(2) 0.0317(6) Uani 1 1 d . . . C19 C 1.6286(4) 0.1108(3) -0.0819(3) 0.0362(8) Uani 1 1 d . . . H19A H 1.6462 0.0994 0.0010 0.043 Uiso 1 1 calc R . . H19B H 1.6938 0.1669 -0.0896 0.043 Uiso 1 1 calc R . . C25 C 1.2391(4) -0.0790(3) -0.4412(3) 0.0320(8) Uani 1 1 d . . . H25A H 1.1862 -0.1464 -0.4591 0.038 Uiso 1 1 calc R . . H25B H 1.2886 -0.0681 -0.4975 0.038 Uiso 1 1 calc R . . C20 C 1.6547(4) 0.0120(3) -0.1362(4) 0.0384(9) Uani 1 1 d . . . H20A H 1.6384 0.0238 -0.2189 0.046 Uiso 1 1 calc R . . H20B H 1.7555 -0.0117 -0.0979 0.046 Uiso 1 1 calc R . . C23 C 1.4701(4) -0.1394(3) -0.3177(3) 0.0357(9) Uani 1 1 d . . . H23A H 1.5309 -0.0991 -0.3518 0.043 Uiso 1 1 calc R . . H23B H 1.4437 -0.2068 -0.3594 0.043 Uiso 1 1 calc R . . C22 C 1.5509(4) -0.1589(3) -0.1912(4) 0.0357(9) Uani 1 1 d . . . H22A H 1.5029 -0.2159 -0.1639 0.043 Uiso 1 1 calc R . . H22B H 1.6504 -0.1818 -0.1803 0.043 Uiso 1 1 calc R . . O15 O 1.2035(3) 0.17767(18) -0.2159(2) 0.0269(5) Uani 1 1 d . . . N12 N 1.0754(3) 0.0041(2) -0.3541(2) 0.0243(6) Uani 1 1 d . . . C26 C 1.1356(4) 0.0101(3) -0.4479(3) 0.0309(8) Uani 1 1 d . . . H26A H 1.1867 0.0777 -0.4429 0.037 Uiso 1 1 calc R . . H26B H 1.0559 0.0077 -0.5232 0.037 Uiso 1 1 calc R . . C14 C 1.0833(4) 0.1969(3) -0.3191(3) 0.0313(8) Uani 1 1 d . . . H14A H 1.1182 0.2167 -0.3822 0.038 Uiso 1 1 calc R . . H14B H 1.0249 0.2556 -0.3065 0.038 Uiso 1 1 calc R . . C11 C 0.9856(4) -0.0896(3) -0.3601(3) 0.0252(7) Uani 1 1 d . . . H11A H 0.9582 -0.0911 -0.2903 0.030 Uiso 1 1 calc R . . H11B H 1.0451 -0.1525 -0.3578 0.030 Uiso 1 1 calc R . . C13 C 0.9919(3) 0.0998(3) -0.3519(3) 0.0290(7) Uani 1 1 d . . . H13A H 0.9412 0.0895 -0.2964 0.035 Uiso 1 1 calc R . . H13B H 0.9179 0.1103 -0.4291 0.035 Uiso 1 1 calc R . . O3W O 1.0942(3) 0.0181(2) -0.0936(2) 0.0309(5) Uani 1 1 d D . . O1W O 1.4038(3) 0.0134(2) 0.0479(2) 0.0366(6) Uani 1 1 d D . . O2W O 1.2473(3) -0.1755(2) -0.1250(2) 0.0306(5) Uani 1 1 d D . . C16 C 1.2981(4) 0.2665(3) -0.1857(3) 0.0337(8) Uani 1 1 d . . . H16A H 1.2543 0.3229 -0.1537 0.040 Uiso 1 1 calc R . . H16B H 1.3146 0.2940 -0.2550 0.040 Uiso 1 1 calc R . . C8 C 0.6072(4) -0.2023(3) -0.5411(3) 0.0290(8) Uani 1 1 d . . . N2 N 0.6616(4) -0.3349(3) -0.4137(3) 0.0379(8) Uani 1 1 d . . . H2 H 0.6558 -0.3924 -0.3762 0.045 Uiso 1 1 calc R . . C9 C 0.7530(4) -0.1875(3) -0.4623(3) 0.0275(7) Uani 1 1 d . . . C3 C 0.5557(4) -0.2965(3) -0.5085(3) 0.0327(8) Uani 1 1 d . . . C10 C 0.8473(4) -0.0974(3) -0.4665(3) 0.0305(7) Uani 1 1 d . . . H10A H 0.7918 -0.0316 -0.4737 0.037 Uiso 1 1 calc R . . H10B H 0.8743 -0.1042 -0.5361 0.037 Uiso 1 1 calc R . . C17 C 1.4381(4) 0.2323(3) -0.0978(4) 0.0364(8) Uani 1 1 d . . . H17A H 1.5121 0.2876 -0.0860 0.044 Uiso 1 1 calc R . . H17B H 1.4256 0.2181 -0.0231 0.044 Uiso 1 1 calc R . . C7 C 0.5179(4) -0.1441(3) -0.6338(3) 0.0310(8) Uani 1 1 d . . . H7 H 0.5510 -0.0808 -0.6563 0.037 Uiso 1 1 calc R . . C6 C 0.3790(4) -0.1808(4) -0.6925(4) 0.0392(9) Uani 1 1 d . . . H6 H 0.3169 -0.1422 -0.7561 0.047 Uiso 1 1 calc R . . C4 C 0.4158(5) -0.3317(3) -0.5681(4) 0.0412(10) Uani 1 1 d . . . H4 H 0.3807 -0.3945 -0.5461 0.049 Uiso 1 1 calc R . . C1 C 0.7796(4) -0.2686(3) -0.3862(3) 0.0346(8) Uani 1 1 d . . . H1 H 0.8670 -0.2784 -0.3231 0.042 Uiso 1 1 calc R . . C5 C 0.3304(5) -0.2731(4) -0.6594(4) 0.0439(10) Uani 1 1 d . . . H5 H 0.2352 -0.2965 -0.7010 0.053 Uiso 1 1 calc R . . O4W O 1.2383(4) 0.0713(3) 0.1806(3) 0.0485(8) Uani 1 1 d D . . O5W O 1.0334(4) -0.0391(3) 0.2335(4) 0.0714(11) Uani 1 1 d D . . H1W2 H 1.239(5) -0.235(2) -0.179(3) 0.044(12) Uiso 1 1 d D . . H1W4 H 1.159(3) 0.033(3) 0.197(3) 0.028(10) Uiso 1 1 d D . . H2W3 H 1.082(5) 0.0862(18) -0.060(4) 0.054(14) Uiso 1 1 d D . . H2W2 H 1.179(4) -0.198(4) -0.087(4) 0.051(14) Uiso 1 1 d D . . H2W1 H 1.499(3) 0.025(4) 0.110(3) 0.050(13) Uiso 1 1 d D . . H1W1 H 1.333(4) 0.022(4) 0.087(4) 0.048(13) Uiso 1 1 d D . . H2W4 H 1.202(9) 0.138(4) 0.139(7) 0.14(3) Uiso 1 1 d D . . H1W5 H 0.949(6) 0.007(5) 0.226(7) 0.13(3) Uiso 1 1 d D . . H2W5 H 0.998(8) -0.084(6) 0.162(4) 0.13(3) Uiso 1 1 d D . . H1W3 H 1.082(7) -0.039(3) -0.044(4) 0.11(2) Uiso 1 1 d 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 I1 0.04096(14) 0.03557(13) 0.03406(12) 0.00972(11) 0.00584(10) -0.00224(11) I2 0.03195(12) 0.03385(12) 0.04587(14) 0.00724(11) 0.01955(10) 0.00015(10) Ca1 0.0207(3) 0.0239(3) 0.0215(3) -0.0016(2) 0.0089(2) -0.0016(2) O24 0.0226(11) 0.0360(13) 0.0231(11) -0.0019(10) 0.0063(9) 0.0080(10) O21 0.0241(12) 0.0343(14) 0.0338(13) -0.0001(11) 0.0104(10) 0.0014(10) O18 0.0255(12) 0.0333(13) 0.0348(13) -0.0043(11) 0.0085(10) -0.0062(10) C19 0.0231(16) 0.046(2) 0.0366(18) -0.0012(17) 0.0063(14) -0.0083(16) C25 0.0302(17) 0.044(2) 0.0223(16) -0.0052(15) 0.0095(14) -0.0004(16) C20 0.0236(17) 0.044(2) 0.048(2) 0.0048(19) 0.0129(16) -0.0022(16) C23 0.0301(18) 0.044(2) 0.039(2) -0.0041(17) 0.0198(17) 0.0098(16) C22 0.0279(18) 0.037(2) 0.042(2) -0.0001(15) 0.0113(17) 0.0090(15) O15 0.0263(12) 0.0202(11) 0.0349(13) -0.0015(10) 0.0117(10) -0.0035(9) N12 0.0233(14) 0.0254(15) 0.0244(13) -0.0001(11) 0.0086(11) 0.0005(11) C26 0.0308(18) 0.041(2) 0.0214(15) 0.0026(15) 0.0094(14) -0.0011(16) C14 0.0295(18) 0.0279(18) 0.0359(19) 0.0037(15) 0.0106(15) 0.0035(15) C11 0.0260(16) 0.0247(16) 0.0239(15) 0.0028(13) 0.0073(13) -0.0001(13) C13 0.0242(15) 0.0281(16) 0.0328(16) 0.0028(16) 0.0076(13) 0.0050(15) O3W 0.0353(14) 0.0268(12) 0.0367(13) -0.0032(11) 0.0202(11) 0.0000(11) O1W 0.0326(14) 0.0511(17) 0.0263(12) -0.0051(12) 0.0106(11) -0.0026(13) O2W 0.0350(13) 0.0259(12) 0.0356(14) -0.0009(11) 0.0181(11) -0.0003(11) C16 0.0353(17) 0.0220(17) 0.048(2) -0.0037(16) 0.0197(16) -0.0068(16) C8 0.0271(16) 0.038(2) 0.0276(17) -0.0085(14) 0.0163(14) -0.0081(14) N2 0.049(2) 0.0322(18) 0.0385(18) 0.0022(14) 0.0221(16) -0.0078(15) C9 0.0306(17) 0.0283(17) 0.0248(17) -0.0047(14) 0.0111(14) -0.0038(14) C3 0.038(2) 0.036(2) 0.0310(18) -0.0058(15) 0.0208(16) -0.0063(16) C10 0.0266(17) 0.0304(18) 0.0295(17) 0.0010(14) 0.0034(14) -0.0037(14) C17 0.036(2) 0.0317(19) 0.041(2) -0.0101(16) 0.0126(17) -0.0075(16) C7 0.0267(17) 0.033(2) 0.036(2) -0.0062(15) 0.0142(15) -0.0022(14) C6 0.0286(18) 0.054(2) 0.037(2) -0.0083(19) 0.0139(16) -0.0016(18) C4 0.043(2) 0.042(2) 0.047(2) -0.0107(19) 0.027(2) -0.0173(19) C1 0.037(2) 0.0359(19) 0.0311(18) -0.0038(16) 0.0120(16) -0.0057(16) C5 0.034(2) 0.054(3) 0.046(2) -0.007(2) 0.0165(18) -0.0109(18) O4W 0.0523(18) 0.056(2) 0.0416(16) -0.0074(14) 0.0213(14) 0.0047(15) O5W 0.061(2) 0.071(3) 0.086(3) -0.015(2) 0.032(2) -0.004(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ca1 O2W 2.370(3) . ? Ca1 O1W 2.427(3) . ? Ca1 O24 2.457(2) . ? Ca1 O3W 2.456(3) . ? Ca1 O15 2.464(2) . ? Ca1 O18 2.476(3) . ? Ca1 O21 2.555(2) . ? Ca1 N12 2.640(3) . ? O24 C25 1.432(4) . ? O24 C23 1.443(4) . ? O21 C22 1.440(5) . ? O21 C20 1.440(5) . ? O18 C17 1.426(5) . ? O18 C19 1.436(4) . ? C19 C20 1.492(6) . ? C25 C26 1.512(5) . ? C23 C22 1.510(6) . ? O15 C14 1.431(4) . ? O15 C16 1.434(4) . ? N12 C11 1.476(4) . ? N12 C26 1.479(4) . ? N12 C13 1.479(4) . ? C14 C13 1.502(5) . ? C11 C10 1.536(4) . ? C16 C17 1.498(5) . ? C8 C7 1.393(5) . ? C8 C3 1.416(5) . ? C8 C9 1.444(5) . ? N2 C3 1.363(5) . ? N2 C1 1.385(5) . ? C9 C1 1.362(5) . ? C9 C10 1.492(5) . ? C3 C4 1.397(5) . ? C7 C6 1.392(5) . ? C6 C5 1.387(6) . ? C4 C5 1.372(7) . ? 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 O2W Ca1 O1W 84.87(10) . . ? O2W Ca1 O24 82.62(9) . . ? O1W Ca1 O24 141.71(9) . . ? O2W Ca1 O3W 76.58(9) . . ? O1W Ca1 O3W 74.36(9) . . ? O24 Ca1 O3W 136.17(9) . . ? O2W Ca1 O15 146.30(9) . . ? O1W Ca1 O15 102.12(9) . . ? O24 Ca1 O15 108.28(8) . . ? O3W Ca1 O15 73.83(8) . . ? O2W Ca1 O18 149.05(9) . . ? O1W Ca1 O18 79.70(9) . . ? O24 Ca1 O18 93.09(9) . . ? O3W Ca1 O18 123.64(9) . . ? O15 Ca1 O18 63.97(8) . . ? O2W Ca1 O21 85.65(9) . . ? O1W Ca1 O21 78.82(9) . . ? O24 Ca1 O21 64.28(8) . . ? O3W Ca1 O21 148.87(9) . . ? O15 Ca1 O21 127.98(8) . . ? O18 Ca1 O21 65.19(9) . . ? O2W Ca1 N12 91.07(9) . . ? O1W Ca1 N12 151.01(9) . . ? O24 Ca1 N12 65.40(8) . . ? O3W Ca1 N12 76.78(9) . . ? O15 Ca1 N12 66.82(8) . . ? O18 Ca1 N12 115.04(9) . . ? O21 Ca1 N12 129.58(9) . . ? C25 O24 C23 112.6(3) . . ? C25 O24 Ca1 123.69(19) . . ? C23 O24 Ca1 123.7(2) . . ? C22 O21 C20 113.2(3) . . ? C22 O21 Ca1 109.5(2) . . ? C20 O21 Ca1 114.9(2) . . ? C17 O18 C19 113.6(3) . . ? C17 O18 Ca1 109.6(2) . . ? C19 O18 Ca1 116.1(2) . . ? O18 C19 C20 106.8(3) . . ? O24 C25 C26 107.4(3) . . ? O21 C20 C19 107.7(3) . . ? O24 C23 C22 107.2(3) . . ? O21 C22 C23 111.5(3) . . ? C14 O15 C16 111.2(3) . . ? C14 O15 Ca1 121.8(2) . . ? C16 O15 Ca1 120.1(2) . . ? C11 N12 C26 113.7(3) . . ? C11 N12 C13 109.9(3) . . ? C26 N12 C13 110.5(3) . . ? C11 N12 Ca1 109.23(18) . . ? C26 N12 Ca1 105.83(19) . . ? C13 N12 Ca1 107.37(19) . . ? N12 C26 C25 111.5(3) . . ? O15 C14 C13 109.6(3) . . ? N12 C11 C10 115.8(3) . . ? N12 C13 C14 113.5(3) . . ? O15 C16 C17 108.3(3) . . ? C7 C8 C3 119.9(3) . . ? C7 C8 C9 133.1(3) . . ? C3 C8 C9 107.0(3) . . ? C3 N2 C1 108.7(3) . . ? C1 C9 C8 105.9(3) . . ? C1 C9 C10 129.5(3) . . ? C8 C9 C10 124.5(3) . . ? N2 C3 C4 131.4(4) . . ? N2 C3 C8 107.8(3) . . ? C4 C3 C8 120.7(4) . . ? C9 C10 C11 113.6(3) . . ? O18 C17 C16 106.7(3) . . ? C8 C7 C6 118.6(4) . . ? C5 C6 C7 120.7(4) . . ? C5 C4 C3 118.2(4) . . ? C9 C1 N2 110.5(3) . . ? C4 C5 C6 121.9(4) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.12 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.848 _refine_diff_density_min -0.407 _refine_diff_density_rms 0.077 data_e:\_georg~1\jxh\jx19e5~1\sss _database_code_CSD 189369 _audit_creation_method SHELXL-97 _chemical_name_systematic 'N,N-bis-(2-(4-hydroxy)ethyl)-diaza-18crown-6.calcium diiodide' _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H49 Ca I2 N3 O8' _chemical_formula_weight 873.60 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' 'Ca' 'Ca' 0.2262 0.3064 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'I' 'I' -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y+1/2, z+1/2' 'x, -y, -z' '-x, y+1/2, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, -y+1, z+1/2' 'x+1/2, -y+1/2, -z' '-x+1/2, y+1, -z+1/2' '-x, -y, -z' 'x, y-1/2, -z-1/2' '-x, y, z' 'x, -y-1/2, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, y, -z-1/2' '-x+1/2, y+1/2, z' 'x+1/2, -y, z-1/2' _cell_length_a 32.992(3) _cell_length_b 17.5027(15) _cell_length_c 12.9431(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 7474.0(11) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.553 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3520 _exptl_absorpt_coefficient_mu 1.867 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.6525 _exptl_absorpt_correction_T_max 0.7065 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 22731 _diffrn_reflns_av_R_equivalents 0.0349 _diffrn_reflns_av_sigmaI/netI 0.0259 _diffrn_reflns_limit_h_min -42 _diffrn_reflns_limit_h_max 42 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 27.12 _reflns_number_total 4203 _reflns_number_gt 3140 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4203 _refine_ls_number_parameters 219 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0402 _refine_ls_R_factor_gt 0.0237 _refine_ls_wR_factor_ref 0.0589 _refine_ls_wR_factor_gt 0.0535 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.010 _refine_ls_shift/su_max 0.032 _refine_ls_shift/su_mean 0.001 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 I1 I 0.5000 0.505026(15) -0.268698(17) 0.04225(8) Uani 1 2 d S . . Ca1 Ca 0.345977(17) 0.5000 0.0000 0.02267(13) Uani 1 2 d S . . O1 O 0.39922(5) 0.43163(10) 0.69583(13) 0.0399(4) Uani 1 1 d D . . N1 N 0.35826(5) 0.36631(10) 0.10787(12) 0.0259(4) Uani 1 1 d . . . C1 C 0.41624(7) 0.36840(13) 0.42884(17) 0.0365(6) Uani 1 1 d . . . H1 H 0.4378 0.3639 0.3804 0.044 Uiso 1 1 calc R . . I2 I 0.2500 0.330584(12) -0.2500 0.03637(7) Uani 1 2 d S . . O2 O 0.40820(4) 0.43155(8) -0.04661(11) 0.0283(3) Uani 1 1 d . . . C2 C 0.42433(7) 0.39804(13) 0.52556(17) 0.0352(6) Uani 1 1 d . . . H2 H 0.4510 0.4139 0.5430 0.042 Uiso 1 1 calc R . . O3 O 0.28322(4) 0.42987(8) 0.03929(11) 0.0313(4) Uani 1 1 d . . . C3 C 0.39307(7) 0.40449(12) 0.59723(17) 0.0307(5) Uani 1 1 d . . . O4 O 0.33294(5) 0.44327(9) -0.16265(12) 0.0331(4) Uani 1 1 d D . . C4 C 0.35431(7) 0.38224(12) 0.57084(17) 0.0316(5) Uani 1 1 d . . . H4 H 0.3328 0.3872 0.6191 0.038 Uiso 1 1 calc R . . C5 C 0.34701(7) 0.35248(12) 0.47290(16) 0.0310(5) Uani 1 1 d . . . H5 H 0.3203 0.3369 0.4553 0.037 Uiso 1 1 calc R . . C6 C 0.37774(7) 0.34497(12) 0.40018(16) 0.0311(5) Uani 1 1 d . . . C7 C 0.36889(8) 0.31578(13) 0.29293(17) 0.0371(6) Uani 1 1 d . . . H7A H 0.3439 0.2844 0.2938 0.045 Uiso 1 1 calc R . . H7B H 0.3915 0.2832 0.2689 0.045 Uiso 1 1 calc R . . C8 C 0.36338(7) 0.38390(12) 0.21881(16) 0.0313(5) Uani 1 1 d . . . H8A H 0.3394 0.4133 0.2418 0.038 Uiso 1 1 calc R . . H8B H 0.3873 0.4177 0.2262 0.038 Uiso 1 1 calc R . . C9 C 0.32143(6) 0.32074(12) 0.08652(18) 0.0316(5) Uani 1 1 d . . . H9A H 0.3216 0.2747 0.1309 0.038 Uiso 1 1 calc R . . H9B H 0.3220 0.3036 0.0137 0.038 Uiso 1 1 calc R . . C10 C 0.28296(7) 0.36423(13) 0.10526(18) 0.0368(5) Uani 1 1 d . . . H10A H 0.2592 0.3317 0.0895 0.044 Uiso 1 1 calc R . . H10B H 0.2813 0.3802 0.1785 0.044 Uiso 1 1 calc R . . C11 C 0.24661(7) 0.47326(15) 0.0456(2) 0.0471(7) Uani 1 1 d . . . H11A H 0.2457 0.5025 0.1110 0.057 Uiso 1 1 calc R . . H11B H 0.2227 0.4390 0.0430 0.057 Uiso 1 1 calc R . . C12 C 0.39442(6) 0.32499(12) 0.06798(16) 0.0298(5) Uani 1 1 d . . . H12A H 0.3893 0.2693 0.0693 0.036 Uiso 1 1 calc R . . H12B H 0.4180 0.3356 0.1130 0.036 Uiso 1 1 calc R . . C13 C 0.40380(7) 0.34977(12) -0.04098(16) 0.0309(5) Uani 1 1 d . . . H13A H 0.4292 0.3250 -0.0644 0.037 Uiso 1 1 calc R . . H13B H 0.3817 0.3332 -0.0875 0.037 Uiso 1 1 calc R . . C14 C 0.44455(6) 0.45757(13) 0.00226(19) 0.0393(6) Uani 1 1 d . . . H14A H 0.4686 0.4369 -0.0341 0.047 Uiso 1 1 calc R . . H14B H 0.4454 0.4401 0.0750 0.047 Uiso 1 1 calc R . . N2 N 0.5000 0.2746(3) 0.0307(5) 0.0900(16) Uani 1 2 d S . . C16 C 0.5000 0.2565(3) 0.1122(6) 0.0784(18) Uani 1 2 d S . . C15 C 0.5000 0.2314(4) 0.2185(5) 0.122(2) Uani 1 2 d S . . H15A H 0.5138 0.1820 0.2237 0.184 Uiso 0.50 1 calc PR . . H15B H 0.4720 0.2262 0.2428 0.184 Uiso 0.50 1 calc PR . . H15C H 0.5142 0.2691 0.2612 0.184 Uiso 0.50 1 calc PR . . H41 H 0.3111(6) 0.4139(13) -0.180(2) 0.052(8) Uiso 1 1 d D . . H42 H 0.3533(7) 0.4345(16) -0.208(2) 0.069(9) Uiso 1 1 d D . . H1O H 0.4246(6) 0.4507(15) 0.705(2) 0.056(8) Uiso 1 1 d 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 I1 0.03125(13) 0.05970(17) 0.03580(13) -0.00496(10) 0.000 0.000 Ca1 0.0204(3) 0.0274(3) 0.0202(3) -0.0021(2) 0.000 0.000 O1 0.0350(10) 0.0544(11) 0.0302(9) -0.0119(8) 0.0022(8) -0.0043(8) N1 0.0286(10) 0.0264(9) 0.0228(9) -0.0023(7) -0.0003(8) 0.0022(8) C1 0.0424(14) 0.0384(14) 0.0288(13) 0.0001(10) 0.0094(10) -0.0025(11) I2 0.02770(11) 0.03596(12) 0.04545(14) 0.000 0.00251(9) 0.000 O2 0.0233(8) 0.0346(9) 0.0271(8) 0.0003(6) 0.0005(6) 0.0030(6) C2 0.0311(12) 0.0407(14) 0.0339(14) -0.0024(10) 0.0039(10) -0.0040(11) O3 0.0224(8) 0.0300(9) 0.0417(9) 0.0022(7) 0.0035(7) 0.0007(6) C3 0.0357(13) 0.0300(12) 0.0264(12) -0.0004(9) 0.0017(10) 0.0032(10) O4 0.0298(9) 0.0428(10) 0.0267(9) -0.0087(7) 0.0008(7) -0.0069(8) C4 0.0290(12) 0.0344(13) 0.0313(13) -0.0014(10) 0.0059(10) 0.0044(10) C5 0.0328(12) 0.0281(12) 0.0322(13) 0.0017(9) -0.0047(9) 0.0016(10) C6 0.0425(14) 0.0260(12) 0.0248(12) 0.0056(9) -0.0020(10) 0.0013(10) C7 0.0525(16) 0.0320(13) 0.0268(12) 0.0007(9) -0.0015(11) 0.0007(11) C8 0.0406(13) 0.0279(12) 0.0253(12) 0.0003(9) 0.0002(10) -0.0010(10) C9 0.0324(13) 0.0278(12) 0.0347(13) 0.0014(9) -0.0010(10) -0.0030(10) C10 0.0311(13) 0.0363(13) 0.0428(14) 0.0061(10) 0.0056(11) -0.0054(10) C11 0.0231(12) 0.0353(14) 0.083(2) 0.0032(13) 0.0105(13) -0.0009(11) C12 0.0285(12) 0.0281(12) 0.0326(13) -0.0016(9) -0.0017(9) 0.0029(9) C13 0.0326(13) 0.0316(13) 0.0284(12) -0.0055(9) 0.0012(10) 0.0073(10) C14 0.0202(11) 0.0434(14) 0.0544(16) 0.0054(12) -0.0051(11) 0.0010(10) N2 0.048(2) 0.066(3) 0.156(5) 0.029(3) 0.000 0.000 C16 0.046(3) 0.050(3) 0.138(6) 0.017(3) 0.000 0.000 C15 0.140(6) 0.082(5) 0.145(7) -0.006(4) 0.000 0.000 _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 Ca1 O4 2.3670(15) . ? Ca1 O4 2.3670(15) 3_565 ? Ca1 O2 2.4521(14) 3_565 ? Ca1 O2 2.4521(14) . ? Ca1 O3 2.4601(14) . ? Ca1 O3 2.4601(14) 3_565 ? Ca1 N1 2.7548(17) 3_565 ? Ca1 N1 2.7548(17) . ? O1 C3 1.377(3) . ? N1 C8 1.478(3) . ? N1 C9 1.479(3) . ? N1 C12 1.488(3) . ? C1 C2 1.381(3) . ? C1 C6 1.385(3) . ? O2 C14 1.431(2) . ? O2 C13 1.440(2) . ? C2 C3 1.392(3) . ? O3 C11 1.429(3) . ? O3 C10 1.432(3) . ? C3 C4 1.380(3) . ? C4 C5 1.392(3) . ? C5 C6 1.390(3) . ? C6 C7 1.508(3) . ? C7 C8 1.541(3) . ? C9 C10 1.500(3) . ? C11 C11 1.507(5) 3_565 ? C12 C13 1.508(3) . ? C14 C14 1.487(5) 3_565 ? N2 C16 1.100(7) . ? C16 C15 1.445(8) . ? 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 O4 Ca1 O4 159.06(8) . 3_565 ? O4 Ca1 O2 125.16(5) . 3_565 ? O4 Ca1 O2 74.24(5) 3_565 3_565 ? O4 Ca1 O2 74.23(5) . . ? O4 Ca1 O2 125.16(5) 3_565 . ? O2 Ca1 O2 66.33(7) 3_565 . ? O4 Ca1 O3 79.73(5) . . ? O4 Ca1 O3 82.68(5) 3_565 . ? O2 Ca1 O3 153.82(5) 3_565 . ? O2 Ca1 O3 120.77(5) . . ? O4 Ca1 O3 82.68(5) . 3_565 ? O4 Ca1 O3 79.73(5) 3_565 3_565 ? O2 Ca1 O3 120.77(5) 3_565 3_565 ? O2 Ca1 O3 153.82(5) . 3_565 ? O3 Ca1 O3 65.38(7) . 3_565 ? O4 Ca1 N1 86.12(5) . 3_565 ? O4 Ca1 N1 96.96(5) 3_565 3_565 ? O2 Ca1 N1 65.58(5) 3_565 3_565 ? O2 Ca1 N1 99.62(5) . 3_565 ? O3 Ca1 N1 130.72(5) . 3_565 ? O3 Ca1 N1 66.12(5) 3_565 3_565 ? O4 Ca1 N1 96.96(5) . . ? O4 Ca1 N1 86.12(5) 3_565 . ? O2 Ca1 N1 99.62(5) 3_565 . ? O2 Ca1 N1 65.58(5) . . ? O3 Ca1 N1 66.12(5) . . ? O3 Ca1 N1 130.72(5) 3_565 . ? N1 Ca1 N1 163.08(7) 3_565 . ? C8 N1 C9 112.80(17) . . ? C8 N1 C12 110.29(16) . . ? C9 N1 C12 109.37(16) . . ? C8 N1 Ca1 109.40(12) . . ? C9 N1 Ca1 104.03(12) . . ? C12 N1 Ca1 110.80(12) . . ? C2 C1 C6 122.1(2) . . ? C14 O2 C13 112.23(16) . . ? C14 O2 Ca1 115.95(12) . . ? C13 O2 Ca1 112.88(11) . . ? C1 C2 C3 119.4(2) . . ? C11 O3 C10 112.78(16) . . ? C11 O3 Ca1 117.26(13) . . ? C10 O3 Ca1 121.93(12) . . ? O1 C3 C4 117.61(19) . . ? O1 C3 C2 122.5(2) . . ? C4 C3 C2 119.9(2) . . ? C3 C4 C5 119.5(2) . . ? C4 C5 C6 121.7(2) . . ? C1 C6 C5 117.4(2) . . ? C1 C6 C7 121.6(2) . . ? C5 C6 C7 120.9(2) . . ? C6 C7 C8 109.50(18) . . ? N1 C8 C7 117.20(18) . . ? N1 C9 C10 113.03(18) . . ? O3 C10 C9 107.80(17) . . ? O3 C11 C11 106.58(18) . 3_565 ? N1 C12 C13 110.45(17) . . ? O2 C13 C12 110.73(16) . . ? O2 C14 C14 107.50(15) . 3_565 ? N2 C16 C15 179.1(7) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.12 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.256 _refine_diff_density_min -0.530 _refine_diff_density_rms 0.070