# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Alamgir Hossain' _publ_contact_author_email ALAMGIR@CHEM.JSUMS.EDU _publ_section_title ; Encapsulated chloride coordinating with two in-in protons of bridgehead amines in an octaprotonated azacryptand ; loop_ _publ_author_name 'Alamgir Hossain' 'Frank R Fronczek' 'Musabbir. A. Saeed' # Attachment 'THEACRCLwithSQUEEZE.cif' data_THEACRCL _database_code_depnum_ccdc_archive 'CCDC 710863' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H56 N8 S3, Cl8, 2.5(H2 O)' _chemical_formula_sum 'C30 H61 Cl8 N8 O2.50 S3' _chemical_formula_weight 953.65 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_space_group_name_H-M 'P 63/m ' _symmetry_space_group_name_Hall '-P 6c' _symmetry_cell_setting Hexagonal loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y, x-y, z' '-x+y, -x, z' 'x-y, x, z+1/2' 'y, -x+y, z+1/2' '-x, -y, -z' 'x, y, -z-1/2' 'y, -x+y, -z' 'x-y, x, -z' '-x+y, -x, -z-1/2' '-y, x-y, -z-1/2' _cell_length_a 12.7445(10) _cell_length_b 12.7445(10) _cell_length_c 19.393(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 120 _cell_volume 2727.9(4) _cell_formula_units_Z 2 _cell_measurement_temperature 100.0(5) _cell_measurement_reflns_used 4358 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 27.9 _exptl_crystal_description fragment _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.161 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1002 _exptl_absorpt_coefficient_mu 0.560 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.850 _exptl_absorpt_correction_T_max 0.896 _exptl_absorpt_process_details 'HKL Scalepack (Otwinowski & Minor 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100.0(5) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD (with Oxford Cryostream)' _diffrn_measurement_method '\w and \f scans ' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 33700 _diffrn_reflns_av_R_equivalents 0.0278 _diffrn_reflns_av_sigmaI/netI 0.0243 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.8 _diffrn_reflns_theta_max 27.9 _reflns_number_total 2241 _reflns_number_gt 1864 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'COLLECT (Nonius, 2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. ; _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^)+(0.0399P)^2^+2.0158P] 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 2241 _refine_ls_number_parameters 77 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.048 _refine_ls_R_factor_gt 0.039 _refine_ls_wR_factor_ref 0.100 _refine_ls_wR_factor_gt 0.096 _refine_ls_goodness_of_fit_ref 1.106 _refine_ls_restrained_S_all 1.106 _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 Cl1 Cl 0.3333 0.6667 0.7500 0.0457(4) Uani 1 6 d S . . Cl2 Cl 0.03408(4) 0.34043(4) 0.43442(2) 0.02860(14) Uani 1 1 d . . . Cl3 Cl 0.6667 0.3333 0.7500 0.0343(3) Uani 1 6 d S . . S1 S -0.05892(6) 0.23791(6) 0.7500 0.02350(16) Uani 1 2 d S . . N1 N 0.3333 0.6667 0.59282(13) 0.0163(5) Uani 1 3 d S . . H1 H 0.3333 0.6667 0.6408 0.020 Uiso 1 3 calc SR . . N2 N 0.04267(13) 0.36354(13) 0.59075(8) 0.0213(3) Uani 1 1 d . . . H2A H 0.0322 0.3657 0.5439 0.026 Uiso 1 1 calc R . . H2B H -0.0080 0.3852 0.6123 0.026 Uiso 1 1 calc R . . C1 C 0.20963(15) 0.56978(15) 0.56897(9) 0.0207(4) Uani 1 1 d . . . H1A H 0.2121 0.5551 0.5190 0.025 Uiso 1 1 calc R . . H1B H 0.1503 0.5973 0.5764 0.025 Uiso 1 1 calc R . . C2 C 0.17009(16) 0.45295(15) 0.60862(10) 0.0240(4) Uani 1 1 d . . . H2C H 0.2234 0.4198 0.5967 0.029 Uiso 1 1 calc R . . H2D H 0.1769 0.4694 0.6588 0.029 Uiso 1 1 calc R . . C3 C 0.00743(17) 0.23605(16) 0.61153(10) 0.0250(4) Uani 1 1 d . . . H3A H -0.0795 0.1815 0.6014 0.030 Uiso 1 1 calc R . . H3B H 0.0545 0.2086 0.5838 0.030 Uiso 1 1 calc R . . C4 C 0.02970(16) 0.22733(15) 0.68618(10) 0.0219(4) Uani 1 1 d . . . C5 C 0.12170(17) 0.21510(16) 0.71336(10) 0.0251(4) Uani 1 1 d . . . H5 H 0.1796 0.2074 0.6862 0.030 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0613(6) 0.0613(6) 0.0146(6) 0.000 0.000 0.0306(3) Cl2 0.0307(3) 0.0362(3) 0.0238(2) -0.00372(19) -0.00503(19) 0.0204(2) Cl3 0.0315(4) 0.0315(4) 0.0401(7) 0.000 0.000 0.01575(19) S1 0.0178(3) 0.0227(3) 0.0274(3) 0.000 0.000 0.0081(2) N1 0.0167(7) 0.0167(7) 0.0155(12) 0.000 0.000 0.0084(3) N2 0.0195(7) 0.0208(7) 0.0217(8) 0.0006(6) -0.0027(6) 0.0087(6) C1 0.0191(8) 0.0194(8) 0.0203(9) -0.0007(7) -0.0050(7) 0.0073(7) C2 0.0197(8) 0.0191(8) 0.0287(10) 0.0004(7) -0.0062(7) 0.0063(7) C3 0.0268(9) 0.0174(8) 0.0261(9) -0.0017(7) -0.0051(8) 0.0076(7) C4 0.0224(8) 0.0158(8) 0.0235(9) -0.0018(7) -0.0002(7) 0.0066(7) C5 0.0280(9) 0.0237(9) 0.0260(10) -0.0007(7) 0.0015(8) 0.0149(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C4 1.7257(19) . ? S1 C4 1.7258(19) 8_557 ? N1 C1 1.5092(18) 4_565 ? N1 C1 1.5092(18) . ? N1 C1 1.5092(18) 3_665 ? N1 H1 0.9300 . ? N2 C2 1.485(2) . ? N2 C3 1.508(2) . ? N2 H2A 0.9200 . ? N2 H2B 0.9200 . ? C1 C2 1.520(2) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 H2C 0.9900 . ? C2 H2D 0.9900 . ? C3 C4 1.490(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.364(3) . ? C5 C5 1.421(4) 8_557 ? C5 H5 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 S1 C4 91.65(13) . 8_557 ? C1 N1 C1 111.04(11) 4_565 . ? C1 N1 C1 111.05(11) 4_565 3_665 ? C1 N1 C1 111.04(11) . 3_665 ? C1 N1 H1 107.8 4_565 . ? C1 N1 H1 107.8 . . ? C1 N1 H1 107.8 3_665 . ? C2 N2 C3 112.74(14) . . ? C2 N2 H2A 109.0 . . ? C3 N2 H2A 109.0 . . ? C2 N2 H2B 109.0 . . ? C3 N2 H2B 109.0 . . ? H2A N2 H2B 107.8 . . ? N1 C1 C2 110.20(14) . . ? N1 C1 H1A 109.6 . . ? C2 C1 H1A 109.6 . . ? N1 C1 H1B 109.6 . . ? C2 C1 H1B 109.6 . . ? H1A C1 H1B 108.1 . . ? N2 C2 C1 109.46(14) . . ? N2 C2 H2C 109.8 . . ? C1 C2 H2C 109.8 . . ? N2 C2 H2D 109.8 . . ? C1 C2 H2D 109.8 . . ? H2C C2 H2D 108.2 . . ? C4 C3 N2 112.02(15) . . ? C4 C3 H3A 109.2 . . ? N2 C3 H3A 109.2 . . ? C4 C3 H3B 109.2 . . ? N2 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? C5 C4 C3 126.22(17) . . ? C5 C4 S1 111.43(14) . . ? C3 C4 S1 122.30(14) . . ? C4 C5 C5 112.74(11) . 8_557 ? C4 C5 H5 123.6 . . ? C5 C5 H5 123.6 8_557 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 N1 C1 C2 -164.75(15) 4_565 . . . ? C1 N1 C1 C2 71.2(3) 3_665 . . . ? C3 N2 C2 C1 163.97(15) . . . . ? N1 C1 C2 N2 173.15(15) . . . . ? C2 N2 C3 C4 55.0(2) . . . . ? N2 C3 C4 C5 -105.1(2) . . . . ? N2 C3 C4 S1 72.25(19) . . . . ? C4 S1 C4 C5 0.58(17) 8_557 . . . ? C4 S1 C4 C3 -177.14(10) 8_557 . . . ? C3 C4 C5 C5 177.17(14) . . . 8_557 ? S1 C4 C5 C5 -0.44(13) . . . 8_557 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 Cl1 0.93 2.12 3.048(3) 180.0 . N2 H2A Cl2 0.92 2.15 3.0425(17) 163.3 . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.0 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.82 _refine_diff_density_min -0.68 _refine_diff_density_rms 0.064 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.000 0.000 42 4 ' ' 2 0.000 0.000 0.500 42 4 ' ' 3 0.005 0.440 0.250 57 8 ' ' 4 -0.005 0.560 0.750 58 8 ' ' 5 0.335 0.667 0.104 50 11 ' ' 6 0.335 0.667 0.396 51 12 ' ' 7 0.435 0.997 0.250 57 7 ' ' 8 0.440 0.435 0.750 58 8 ' ' 9 0.565 1.005 0.750 58 8 ' ' 10 0.561 0.564 0.250 58 7 ' ' 11 0.667 0.333 0.603 49 10 ' ' 12 0.667 0.333 0.897 51 12 ' ' _platon_squeeze_details ; Contribution from disordered solvent was removed using SQUEEZE (Spek, 1999), amounting to 99 electrons per unit cell. With Z=2, this amounts to approximately 2.5 H~2~O molecules per macrocycle. This solvent is included in the formula, density, etc., but is not included in the model. ; # END OF CIF