#------------------------------------------------------------------------------ #$Date: 2012-10-25 12:42:06 +0300 (Thu, 25 Oct 2012) $ #$Revision: 68347 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/11/49/4114963.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_4114963 loop_ _publ_author_name 'Christopher J. Woods' 'Salvatore Camiolo' 'Mark E. Light' 'Simon J. Coles' 'Michael B. Hursthouse' 'Michael A. King' 'Philip A. Gale' 'Jonathan W. Essex' _publ_section_title ; Fluoride-Selective Binding in a New Deep Cavity Calix[4]pyrrole: Experiment and Theory ; _journal_name_full 'Journal of the American Chemical Society' _journal_page_first 8644 _journal_page_last 8652 _journal_volume 124 _journal_year 2002 _chemical_formula_sum 'C72 H88 F N5 O8' _chemical_formula_weight 1170.47 _chemical_name_systematic ; ? ; _space_group_IT_number 130 _symmetry_cell_setting tetragonal _symmetry_space_group_name_Hall '-P 4a 2ac' _symmetry_space_group_name_H-M 'P 4/n c c :2' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 17.2489(5) _cell_length_b 17.2489(5) _cell_length_c 24.0303(8) _cell_measurement_temperature 150(2) _cell_volume 7149.6(4) _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 150(2) _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.991 _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1027 _diffrn_reflns_av_sigmaI/netI 0.0400 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_number 27239 _diffrn_reflns_theta_full 20.92 _diffrn_reflns_theta_max 20.92 _diffrn_reflns_theta_min 3.14 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_T_max 0.9986 _exptl_absorpt_correction_T_min 0.9899 _exptl_crystal_density_diffrn 1.087 _exptl_crystal_F_000 2512 _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.02 _refine_diff_density_max 0.664 _refine_diff_density_min -0.351 _refine_diff_density_rms 0.064 _refine_ls_extinction_coef 0.004(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.503 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 217 _refine_ls_number_reflns 1895 _refine_ls_number_restraints 56 _refine_ls_restrained_S_all 1.495 _refine_ls_R_factor_all 0.1244 _refine_ls_R_factor_gt 0.1126 _refine_ls_shift/su_max 1.151 _refine_ls_shift/su_mean 0.031 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.3421 _refine_ls_wR_factor_ref 0.3517 _reflns_number_gt 1707 _reflns_number_total 1895 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file ja025572t_s1_1.cif _[local]_cod_data_source_block s92 _[local]_cod_cif_authors_sg_H-M 'P 4/n c c' _cod_database_code 4114963 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-y+1/2, x, z' 'y, -x+1/2, z' '-x, y+1/2, -z+1/2' 'x+1/2, -y, -z+1/2' 'y+1/2, x+1/2, -z+1/2' '-y, -x, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'y-1/2, -x, -z' '-y, x-1/2, -z' 'x, -y-1/2, z-1/2' '-x-1/2, y, z-1/2' '-y-1/2, -x-1/2, z-1/2' 'y, x, z-1/2' 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 F1 F 0.2500 0.2500 0.1144(2) 0.0394(18) Uani 1 4 d S . . O1 O 0.9997(3) 0.1330(3) 0.44621(18) 0.0556(15) Uani 1 1 d . . . N1 N 1.1244(3) 0.2948(3) 0.6758(2) 0.0444(16) Uani 1 1 d . . . H1 H 1.1615 0.2816 0.6525 0.053 Uiso 1 1 calc R . . O2 O 0.8751(3) 0.1048(3) 0.4591(2) 0.0754(18) Uani 1 1 d . . . C3 C 1.0635(3) 0.1613(4) 0.6791(2) 0.0458(18) Uani 1 1 d . . . C7 C 1.0495(3) 0.1552(4) 0.6148(3) 0.0459(18) Uani 1 1 d . . . C8 C 1.0051(3) 0.2112(4) 0.5879(3) 0.0490(18) Uani 1 1 d . . . H8 H 0.9874 0.2552 0.6080 0.059 Uiso 1 1 calc R . . C2 C 1.0693(4) 0.2447(4) 0.6973(3) 0.0468(18) Uani 1 1 d . . . C11 C 1.0571(4) 0.0845(4) 0.5291(3) 0.0494(19) Uani 1 1 d . . . H11 H 1.0748 0.0408 0.5086 0.059 Uiso 1 1 calc R . . C4 C 1.1326(4) 0.1125(3) 0.6961(2) 0.0423(17) Uani 1 1 d . . . C9 C 0.9867(4) 0.2032(4) 0.5326(3) 0.0527(19) Uani 1 1 d . . . H9 H 0.9559 0.2413 0.5146 0.063 Uiso 1 1 calc R . . C12 C 1.0754(4) 0.0928(4) 0.5850(3) 0.0513(19) Uani 1 1 d . . . H12 H 1.1063 0.0546 0.6029 0.062 Uiso 1 1 calc R . . C10 C 1.0126(4) 0.1408(4) 0.5036(3) 0.0512(19) Uani 1 1 d . . . C1 C 1.0241(4) 0.2872(4) 0.7322(3) 0.059(2) Uani 1 1 d . . . H1A H 0.9815 0.2681 0.7532 0.071 Uiso 1 1 calc R . . C13 C 0.9273(5) 0.1166(4) 0.4282(3) 0.058(2) Uani 1 1 d . . . C5 C 1.1348(4) 0.0515(4) 0.7318(2) 0.054(2) Uani 1 1 d . . . H5 H 1.0926 0.0311 0.7526 0.064 Uiso 1 1 calc R . . C14 C 0.9243(5) 0.1141(5) 0.3664(3) 0.076(2) Uani 1 1 d . . . H14A H 0.9756 0.1263 0.3513 0.114 Uiso 1 1 calc R . . H14B H 0.8866 0.1523 0.3530 0.114 Uiso 1 1 calc R . . H14C H 0.9087 0.0622 0.3543 0.114 Uiso 1 1 calc R . . C6 C 0.9905(4) 0.1259(4) 0.7063(3) 0.061(2) Uani 1 1 d . . . H6A H 0.9849 0.0719 0.6944 0.091 Uiso 1 1 calc R . . H6B H 0.9447 0.1554 0.6948 0.091 Uiso 1 1 calc R . . H6C H 0.9956 0.1280 0.7469 0.091 Uiso 1 1 calc R . . N2A N 0.2500 0.2500 0.3583(4) 0.063(3) Uani 0.50 4 d SPD . 1 C17A C 0.1834(7) 0.2761(9) 0.3943(6) 0.073(4) Uani 0.50 1 d PDU A 1 H17A H 0.2023 0.3145 0.4218 0.087 Uiso 0.50 1 calc PR A 1 H17B H 0.1626 0.2311 0.4151 0.087 Uiso 0.50 1 calc PR A 1 C18A C 0.1179(7) 0.3127(8) 0.3590(5) 0.141(4) Uani 0.50 1 d PDU A 1 H18A H 0.1235 0.3697 0.3560 0.169 Uiso 0.50 1 calc PR A 1 H18B H 0.1150 0.2897 0.3214 0.169 Uiso 0.50 1 calc PR A 1 C19A C 0.0522(12) 0.2912(15) 0.3929(13) 0.145(11) Uani 0.50 1 d PDU A 1 H19A H 0.0695 0.2861 0.4320 0.174 Uiso 0.50 1 calc PR A 1 H19B H 0.0333 0.2398 0.3806 0.174 Uiso 0.50 1 calc PR A 1 C20A C -0.0158(6) 0.3491(6) 0.3907(5) 0.112(3) Uani 0.50 1 d PDU A 1 H20A H 0.0041 0.4011 0.3825 0.168 Uiso 0.50 1 calc PR A 1 H20B H -0.0426 0.3497 0.4267 0.168 Uiso 0.50 1 calc PR A 1 H20C H -0.0522 0.3335 0.3615 0.168 Uiso 0.50 1 calc PR A 1 N2B N 0.2500 0.2500 0.3583(4) 0.063(3) Uani 0.50 4 d SPD . 2 C17B C 0.1836(7) 0.2772(8) 0.3210(5) 0.062(4) Uani 0.50 1 d PDU B 2 H17C H 0.1627 0.2330 0.2994 0.074 Uiso 0.50 1 calc PR B 2 H17D H 0.2025 0.3168 0.2945 0.074 Uiso 0.50 1 calc PR B 2 C18B C 0.1179(7) 0.3127(8) 0.3590(5) 0.141(4) Uani 0.50 1 d PDU B 2 H18C H 0.1408 0.3652 0.3622 0.169 Uiso 0.50 1 calc PR B 2 H18D H 0.0787 0.3188 0.3293 0.169 Uiso 0.50 1 calc PR B 2 C19B C 0.0608(9) 0.3208(16) 0.4086(8) 0.105(8) Uani 0.50 1 d PDU B 2 H19C H 0.0547 0.2698 0.4269 0.126 Uiso 0.50 1 calc PR B 2 H19D H 0.0828 0.3573 0.4362 0.126 Uiso 0.50 1 calc PR B 2 C20B C -0.0158(6) 0.3491(6) 0.3907(5) 0.112(3) Uani 0.50 1 d PDU B 2 H20D H -0.0127 0.4047 0.3824 0.168 Uiso 0.50 1 calc PR B 2 H20E H -0.0536 0.3405 0.4205 0.168 Uiso 0.50 1 calc PR B 2 H20F H -0.0322 0.3210 0.3573 0.168 Uiso 0.50 1 calc PR B 2 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 F1 0.048(2) 0.048(2) 0.023(3) 0.000 0.000 0.000 O1 0.057(3) 0.070(3) 0.040(3) -0.004(2) -0.005(2) -0.012(2) N1 0.052(3) 0.053(4) 0.028(3) 0.001(3) 0.012(2) 0.002(3) O2 0.067(4) 0.092(4) 0.068(4) 0.000(3) -0.003(3) -0.019(3) C3 0.052(4) 0.054(4) 0.031(3) 0.002(3) 0.007(3) -0.007(3) C7 0.042(4) 0.049(4) 0.047(4) 0.006(4) 0.000(3) -0.008(3) C8 0.046(4) 0.052(4) 0.049(4) -0.006(3) 0.008(3) -0.005(3) C2 0.047(4) 0.057(4) 0.036(4) 0.005(3) 0.011(3) 0.006(4) C11 0.051(4) 0.052(4) 0.045(4) -0.002(3) 0.002(3) 0.001(3) C4 0.050(4) 0.048(4) 0.029(3) 0.012(3) 0.005(3) 0.004(3) C9 0.059(4) 0.055(5) 0.044(4) 0.010(3) -0.005(3) 0.002(4) C12 0.064(4) 0.053(4) 0.037(4) 0.000(3) -0.003(3) -0.002(3) C10 0.055(4) 0.063(5) 0.035(4) 0.002(4) -0.004(3) -0.013(4) C1 0.056(4) 0.083(6) 0.040(4) 0.006(4) 0.012(3) -0.009(4) C13 0.074(6) 0.042(4) 0.058(5) -0.004(3) -0.021(5) -0.005(4) C5 0.060(5) 0.070(5) 0.031(4) 0.007(3) 0.014(3) 0.000(4) C14 0.093(6) 0.083(6) 0.051(5) 0.002(4) -0.026(4) 0.003(5) C6 0.065(5) 0.074(5) 0.043(4) 0.004(3) 0.011(3) -0.010(4) N2A 0.076(5) 0.076(5) 0.037(6) 0.000 0.000 0.000 C17A 0.073(4) 0.073(4) 0.073(4) 0.0001(10) -0.0001(10) 0.0003(10) C18A 0.141(4) 0.141(4) 0.141(4) -0.0004(7) -0.0004(7) 0.0002(7) C19A 0.145(11) 0.145(11) 0.145(11) 0.0002(11) -0.0004(11) -0.0002(11) C20A 0.112(4) 0.112(4) 0.112(4) 0.0000(7) 0.0002(7) 0.0001(7) N2B 0.076(5) 0.076(5) 0.037(6) 0.000 0.000 0.000 C17B 0.062(4) 0.062(4) 0.062(4) 0.0000(10) -0.0004(10) -0.0003(10) C18B 0.141(4) 0.141(4) 0.141(4) -0.0004(7) -0.0004(7) 0.0002(7) C19B 0.105(8) 0.105(8) 0.105(8) 0.0003(11) -0.0002(11) -0.0004(11) C20B 0.112(4) 0.112(4) 0.112(4) 0.0000(7) 0.0002(7) 0.0001(7) 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C13 O1 C10 118.8(5) . . C4 N1 C2 109.7(5) 4_665 . C2 C3 C4 113.6(5) . . C2 C3 C6 107.9(5) . . C4 C3 C6 107.9(5) . . C2 C3 C7 111.2(5) . . C4 C3 C7 110.4(5) . . C6 C3 C7 105.4(5) . . C12 C7 C8 119.0(6) . . C12 C7 C3 121.2(6) . . C8 C7 C3 119.6(6) . . C9 C8 C7 120.4(6) . . C1 C2 N1 106.7(6) . . C1 C2 C3 131.1(6) . . N1 C2 C3 122.1(5) . . C10 C11 C12 118.9(6) . . C5 C4 N1 108.5(5) . 3_645 C5 C4 C3 128.6(6) . . N1 C4 C3 122.9(5) 3_645 . C10 C9 C8 120.0(6) . . C7 C12 C11 120.9(6) . . C9 C10 C11 120.9(6) . . C9 C10 O1 121.9(6) . . C11 C10 O1 117.1(6) . . C2 C1 C5 108.4(6) . 4_665 O2 C13 O1 122.5(7) . . O2 C13 C14 126.5(7) . . O1 C13 C14 111.1(8) . . C4 C5 C1 106.7(6) . 3_645 C17A N2A C17A 70.7(6) 4 2 C17A N2A C17A 109.9(12) 4 3 C17A N2A C17A 70.7(6) 2 3 C17A N2A C17A 70.7(6) 4 . C17A N2A C17A 109.9(12) 2 . C17A N2A C17A 70.7(6) 3 . N2A C17A C18A 111.3(10) . . C19A C18A C17A 99.2(13) . . C18A C19A C20A 114.3(15) . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 O1 C13 1.351(9) . O1 C10 1.404(8) . N1 C4 1.360(7) 4_665 N1 C2 1.386(8) . O2 C13 1.186(9) . C3 C2 1.506(9) . C3 C4 1.515(8) . C3 C6 1.545(9) . C3 C7 1.569(9) . C7 C12 1.366(9) . C7 C8 1.391(9) . C8 C9 1.374(9) . C2 C1 1.359(9) . C11 C10 1.380(9) . C11 C12 1.389(9) . C4 C5 1.359(9) . C4 N1 1.360(7) 3_645 C9 C10 1.357(9) . C1 C5 1.427(10) 4_665 C13 C14 1.485(11) . C5 C1 1.427(10) 3_645 N2A C17A 1.507(13) 4 N2A C17A 1.507(13) 2 N2A C17A 1.507(13) 3 N2A C17A 1.507(13) . C17A C18A 1.548(14) . C18A C19A 1.444(17) . C19A C20A 1.542(17) . loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 F1 0.88 1.86 2.732(6) 170.0 13_666