#------------------------------------------------------------------------------ #$Date: 2024-10-25 01:09:50 +0300 (Fri, 25 Oct 2024) $ #$Revision: 295608 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/29/1572937.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_1572937 loop_ _publ_author_name 'Virtue, Jemma I.' 'Tsoukatos, Steven' 'Johnston, Martin' 'Bloch, Witold' _publ_section_title ; Halide-triggered assembly and selective bisulfate recognition in a quadruply interlocked coordination cage ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D4SC04913F _journal_year 2024 _chemical_formula_moiety 'C21 H14 N6' _chemical_formula_sum 'C21 H14 N6' _chemical_formula_weight 350.38 _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' _space_group_name_H-M_alt 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2019/3 _audit_update_record ; 2024-10-18 deposited with the CCDC. 2024-10-24 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 94.79(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 20.740(4) _cell_length_b 4.4250(9) _cell_length_c 18.376(4) _cell_measurement_reflns_used 2759 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 18.31 _cell_measurement_theta_min 0.67 _cell_volume 1680.6(6) _computing_cell_refinement 'XDS (Kabsch, 1993)' _computing_data_collection 'BluIce (McPhillips, 2002)' _computing_data_reduction 'XDS (Kabsch, 1993)' _computing_molecular_graphics 'shelXle (Huebschle, 2014)' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT-2018/3 (Sheldrick, 2018)' _diffrn_ambient_temperature 100(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.842 _diffrn_measurement_device_type 'ADSC Quantum 315r' _diffrn_measurement_method 'Phi Scan' _diffrn_radiation_monochromator 'Silicon Double Crystal' _diffrn_radiation_type Synchrotron _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1128 _diffrn_reflns_av_unetI/netI 0.0687 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.842 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_number 13396 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.842 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 31.902 _diffrn_reflns_theta_min 1.971 _diffrn_source 'MX2 Beamline Australian Synchrotron' _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.385 _exptl_crystal_description rod _exptl_crystal_F_000 728 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent' _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.04 _refine_diff_density_max 0.366 _refine_diff_density_min -0.333 _refine_diff_density_rms 0.090 _refine_ls_extinction_coef 0.028(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2019/2 (Sheldrick 2019)' _refine_ls_goodness_of_fit_ref 1.093 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 124 _refine_ls_number_reflns 2449 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.093 _refine_ls_R_factor_all 0.0683 _refine_ls_R_factor_gt 0.0608 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1126P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1726 _refine_ls_wR_factor_ref 0.1800 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1995 _reflns_number_total 2449 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4sc04913f2.cif _cod_data_source_block sol_a _cod_original_cell_volume 1680.5(6) _cod_original_sg_symbol_H-M 'C 2/c' _cod_database_code 1572937 _shelx_shelxl_version_number 2019/3 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_res_file ; TITL sol_a.res in C2/c sol_a.res created by SHELXL-2019/3 at 11:26:40 on 15-Oct-2024 REM Old TITL sol in C2/c REM SHELXT solution in C2/c: R1 0.143, Rweak 0.001, Alpha 0.015 REM 0.253 for 229 systematic absences, Orientation as input REM Formula found by SHELXT: C21 N6 CELL 0.71073 20.7397 4.4250 18.3760 90.000 94.788 90.000 ZERR 4.000 0.0041 0.0009 0.0037 0.000 0.030 0.000 LATT 7 SYMM -X, Y, 1/2-Z SFAC C H N UNIT 84 56 24 L.S. 10 ACTA BOND TEMP 100 LIST 4 BOND $H FMAP 2 PLAN 20 WGHT 0.112600 EXTI 0.027724 FVAR 0.64116 N1 3 0.853547 0.063615 0.336602 11.00000 0.04888 0.03298 = 0.02948 0.00031 0.01220 0.00490 C2 1 0.886194 0.041466 0.402693 11.00000 0.04151 0.03108 = 0.03219 0.00481 0.00915 0.00236 AFIX 43 H2 2 0.922629 -0.081626 0.408007 11.00000 -1.20000 AFIX 0 C3 1 0.867486 0.196123 0.463596 11.00000 0.04173 0.03322 = 0.02802 0.00223 0.00211 0.00129 AFIX 43 H3 2 0.891277 0.175363 0.508503 11.00000 -1.20000 AFIX 0 C4 1 0.813457 0.380507 0.457068 11.00000 0.03940 0.02924 = 0.02185 0.00010 0.00539 0.00137 AFIX 43 H4 2 0.800769 0.487967 0.496959 11.00000 -1.20000 AFIX 0 C6 1 0.800933 0.238930 0.330020 11.00000 0.04297 0.02953 = 0.02246 -0.00116 0.00780 -0.00074 AFIX 43 H6 2 0.778162 0.254428 0.284383 11.00000 -1.20000 AFIX 0 C5 1 0.778217 0.401034 0.388417 11.00000 0.03645 0.02468 = 0.02306 0.00097 0.00589 -0.00237 C9 1 0.613632 0.890404 0.350174 11.00000 0.03668 0.02615 = 0.02136 -0.00217 0.00171 -0.00108 C10 1 0.599273 1.094039 0.293927 11.00000 0.03641 0.02657 = 0.02250 -0.00226 0.00382 -0.00112 AFIX 43 H10 2 0.626031 1.149254 0.257992 11.00000 -1.20000 AFIX 0 N11 3 0.538971 1.196726 0.301369 11.00000 0.03784 0.02475 = 0.02191 0.00040 0.00291 -0.00088 N12 3 0.511434 1.069928 0.358849 11.00000 0.04128 0.03165 = 0.02336 0.00273 0.00636 0.00121 C13 1 0.556906 0.885747 0.388426 11.00000 0.04164 0.03057 = 0.02230 0.00332 0.00407 0.00048 AFIX 43 H13 2 0.552152 0.767377 0.429454 11.00000 -1.20000 AFIX 0 C14 1 0.500000 1.382922 0.250000 10.50000 0.04008 0.02362 = 0.02428 0.00000 0.00114 0.00000 AFIX 23 H14A 2 0.527974 1.511644 0.223726 10.50000 -1.20000 H14B 2 0.472025 1.511633 0.276275 10.50000 -1.20000 AFIX 0 C8 1 0.671568 0.723234 0.365022 11.00000 0.03809 0.02704 = 0.02095 -0.00112 0.00287 -0.00283 C7 1 0.720988 0.580025 0.376960 11.00000 0.04064 0.02841 = 0.02100 -0.00074 0.00419 -0.00265 HKLF 4 REM sol_a.res in C2/c REM wR2 = 0.1800, GooF = S = 1.093, Restrained GooF = 1.093 for all data REM R1 = 0.0608 for 1995 Fo > 4sig(Fo) and 0.0683 for all 2449 data REM 124 parameters refined using 0 restraints END WGHT 0.1133 0.0000 REM Highest difference peak 0.366, deepest hole -0.333, 1-sigma level 0.090 Q1 1 0.5132 1.1954 0.2428 11.00000 0.05 0.29 Q2 1 0.5650 1.1721 0.2966 11.00000 0.05 0.28 Q3 1 0.9183 0.2086 0.5003 11.00000 0.05 0.27 Q4 1 0.7494 0.2490 0.2762 11.00000 0.05 0.25 Q5 1 0.5990 0.7542 0.5117 11.00000 0.05 0.24 Q6 1 0.7562 0.0928 0.2502 11.00000 0.05 0.24 Q7 1 0.4737 1.2929 0.2398 11.00000 0.05 0.24 Q8 1 0.7933 0.3821 0.2647 11.00000 0.05 0.24 Q9 1 0.8684 -0.0536 0.4663 11.00000 0.05 0.24 Q10 1 0.8175 0.0970 0.4675 11.00000 0.05 0.24 Q11 1 0.8323 0.3046 0.4625 11.00000 0.05 0.23 Q12 1 0.5475 1.4794 0.2238 11.00000 0.05 0.23 Q13 1 0.4700 1.0740 0.3000 11.00000 0.05 0.23 Q14 1 0.5834 0.6690 0.4750 11.00000 0.05 0.22 Q15 1 0.9189 0.3157 0.5229 11.00000 0.05 0.22 Q16 1 0.7832 0.3356 0.2169 11.00000 0.05 0.22 Q17 1 0.8367 0.8111 0.4895 11.00000 0.05 0.22 Q18 1 0.5482 1.1141 0.2508 11.00000 0.05 0.22 Q19 1 0.7900 0.1078 0.2882 11.00000 0.05 0.22 Q20 1 0.5877 0.9344 0.4700 11.00000 0.05 0.22 ; _shelx_res_checksum 36002 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.85355(6) 0.0636(3) 0.33660(6) 0.0366(3) Uani 1 1 d . . . . . C2 C 0.88619(7) 0.0415(3) 0.40269(7) 0.0346(3) Uani 1 1 d . . . . . H2 H 0.922629 -0.081626 0.408007 0.041 Uiso 1 1 calc R U . . . C3 C 0.86749(7) 0.1961(3) 0.46360(7) 0.0344(3) Uani 1 1 d . . . . . H3 H 0.891277 0.175363 0.508503 0.041 Uiso 1 1 calc R U . . . C4 C 0.81346(6) 0.3805(3) 0.45707(6) 0.0300(3) Uani 1 1 d . . . . . H4 H 0.800769 0.487967 0.496959 0.036 Uiso 1 1 calc R U . . . C6 C 0.80093(7) 0.2389(3) 0.33002(6) 0.0314(3) Uani 1 1 d . . . . . H6 H 0.778162 0.254428 0.284383 0.038 Uiso 1 1 calc R U . . . C5 C 0.77822(6) 0.4010(2) 0.38842(6) 0.0279(3) Uani 1 1 d . . . . . C9 C 0.61363(6) 0.8904(2) 0.35017(6) 0.0281(3) Uani 1 1 d . . . . . C10 C 0.59927(6) 1.0940(2) 0.29393(6) 0.0284(3) Uani 1 1 d . . . . . H10 H 0.626031 1.149254 0.257992 0.034 Uiso 1 1 calc R U . . . N11 N 0.53897(5) 1.1967(2) 0.30137(5) 0.0281(3) Uani 1 1 d . . . . . N12 N 0.51143(6) 1.0699(2) 0.35885(6) 0.0319(3) Uani 1 1 d . . . . . C13 C 0.55691(7) 0.8857(3) 0.38843(7) 0.0314(3) Uani 1 1 d . . . . . H13 H 0.552152 0.767377 0.429454 0.038 Uiso 1 1 calc R U . . . C14 C 0.500000 1.3829(4) 0.250000 0.0294(4) Uani 1 2 d S T P . . H14A H 0.527974 1.511644 0.223726 0.035 Uiso 0.5 1 calc R U P . . H14B H 0.472025 1.511633 0.276275 0.035 Uiso 0.5 1 calc R U P . . C8 C 0.67157(6) 0.7232(3) 0.36502(6) 0.0287(3) Uani 1 1 d . . . . . C7 C 0.72099(7) 0.5800(3) 0.37696(6) 0.0299(3) 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 N1 0.0489(7) 0.0330(6) 0.0295(6) 0.0003(4) 0.0122(5) 0.0049(4) C2 0.0415(7) 0.0311(6) 0.0322(6) 0.0048(5) 0.0091(5) 0.0024(5) C3 0.0417(7) 0.0332(6) 0.0280(6) 0.0022(5) 0.0021(5) 0.0013(5) C4 0.0394(7) 0.0292(6) 0.0218(5) 0.0001(4) 0.0054(5) 0.0014(4) C6 0.0430(7) 0.0295(6) 0.0225(5) -0.0012(4) 0.0078(5) -0.0007(5) C5 0.0365(7) 0.0247(5) 0.0231(5) 0.0010(4) 0.0059(4) -0.0024(4) C9 0.0367(7) 0.0261(6) 0.0214(5) -0.0022(4) 0.0017(4) -0.0011(4) C10 0.0364(7) 0.0266(5) 0.0225(5) -0.0023(4) 0.0038(4) -0.0011(4) N11 0.0378(6) 0.0247(5) 0.0219(5) 0.0004(4) 0.0029(4) -0.0009(4) N12 0.0413(6) 0.0316(5) 0.0234(5) 0.0027(4) 0.0064(4) 0.0012(4) C13 0.0416(7) 0.0306(6) 0.0223(5) 0.0033(4) 0.0041(5) 0.0005(5) C14 0.0401(9) 0.0236(7) 0.0243(7) 0.000 0.0011(6) 0.000 C8 0.0381(7) 0.0270(5) 0.0210(5) -0.0011(4) 0.0029(4) -0.0028(4) C7 0.0406(7) 0.0284(6) 0.0210(5) -0.0007(4) 0.0042(4) -0.0027(4) 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' 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 C6 N1 C2 118.05(11) . . ? N1 C2 C3 122.46(13) . . ? N1 C2 H2 118.8 . . ? C3 C2 H2 118.8 . . ? C4 C3 C2 119.84(12) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C3 C4 C5 118.18(11) . . ? C3 C4 H4 120.9 . . ? C5 C4 H4 120.9 . . ? N1 C6 C5 123.43(12) . . ? N1 C6 H6 118.3 . . ? C5 C6 H6 118.3 . . ? C6 C5 C4 118.02(12) . . ? C6 C5 C7 119.89(11) . . ? C4 C5 C7 122.08(11) . . ? C10 C9 C8 127.52(11) . . ? C10 C9 C13 104.09(11) . . ? C8 C9 C13 128.38(10) . . ? N11 C10 C9 106.68(11) . . ? N11 C10 H10 126.7 . . ? C9 C10 H10 126.7 . . ? C10 N11 N12 113.09(10) . . ? C10 N11 C14 126.71(9) . . ? N12 N11 C14 119.50(9) . . ? C13 N12 N11 103.92(10) . . ? N12 C13 C9 112.20(10) . . ? N12 C13 H13 123.9 . . ? C9 C13 H13 123.9 . . ? N11 C14 N11 110.62(13) . 2_655 ? N11 C14 H14A 109.5 . . ? N11 C14 H14A 109.5 2_655 . ? N11 C14 H14B 109.5 . . ? N11 C14 H14B 109.5 2_655 . ? H14A C14 H14B 108.1 . . ? C7 C8 C9 179.35(12) . . ? C8 C7 C5 177.27(13) . . ? 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 C6 1.3361(17) . ? N1 C2 1.3438(19) . ? C2 C3 1.3942(18) . ? C2 H2 0.9300 . ? C3 C4 1.3832(18) . ? C3 H3 0.9300 . ? C4 C5 1.4071(18) . ? C4 H4 0.9300 . ? C6 C5 1.4044(16) . ? C6 H6 0.9300 . ? C5 C7 1.4278(18) . ? C9 C10 1.3848(17) . ? C9 C8 1.4180(18) . ? C9 C13 1.4201(18) . ? C10 N11 1.3483(17) . ? C10 H10 0.9300 . ? N11 N12 1.3628(14) . ? N11 C14 1.4477(14) . ? N12 C13 1.3280(17) . ? C13 H13 0.9300 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C8 C7 1.2094(18) . ?