#------------------------------------------------------------------------------ #$Date: 2020-05-13 04:35:15 +0300 (Wed, 13 May 2020) $ #$Revision: 252006 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/05/7240500.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_7240500 loop_ _publ_author_name 'Fotovi\'c, Luka' 'Stilinovic, Vladimir' _publ_section_title ; Halogenide anions as halogen and hydrogen bond acceptors in iodopyridinium halogenides ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/D0CE00534G _journal_year 2020 _chemical_formula_sum 'C10 H10 Cl I3 N2' _chemical_formula_weight 574.35 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2020-04-07 deposited with the CCDC. 2020-05-11 downloaded from the CCDC. ; _cell_angle_alpha 89.566(5) _cell_angle_beta 70.547(6) _cell_angle_gamma 81.668(6) _cell_formula_units_Z 2 _cell_length_a 8.2027(6) _cell_length_b 8.8661(5) _cell_length_c 11.4800(7) _cell_measurement_reflns_used 2325 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 37.4488 _cell_measurement_theta_min 3.7466 _cell_volume 778.18(9) _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution ; SHELXT (Sheldrick, G. M. (2015). Acta Cryst. A71, 3-8.) ; _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 16.3426 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.990 _diffrn_measurement_device_type ; Oxford Diffraction Xcalibur CCD diffractometer ; _diffrn_measurement_method '\w scan' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0546 _diffrn_reflns_av_unetI/netI 0.0716 _diffrn_reflns_Laue_measured_fraction_full 0.994 _diffrn_reflns_Laue_measured_fraction_max 0.990 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 5878 _diffrn_reflns_point_group_measured_fraction_full 0.994 _diffrn_reflns_point_group_measured_fraction_max 0.990 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.995 _diffrn_reflns_theta_min 3.765 _diffrn_source 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 6.176 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.40084 _exptl_absorpt_correction_type multi-scan _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 2.451 _exptl_crystal_description block _exptl_crystal_F_000 520 _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.18 _refine_diff_density_max 0.662 _refine_diff_density_min -1.182 _refine_diff_density_rms 0.182 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.921 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 145 _refine_ls_number_reflns 3374 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.921 _refine_ls_R_factor_all 0.0647 _refine_ls_R_factor_gt 0.0414 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0554P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0902 _refine_ls_wR_factor_ref 0.1126 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2243 _reflns_number_total 3374 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ce00534g2.cif _cod_data_source_block (2-IPyH)2ClI _cod_database_code 7240500 _shelx_shelxl_version_number 2018/3 _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 shelxt_a.res in P-1 shelx.res created by SHELXL-2018/3 at 12:03:28 on 28-Jun-2019 CELL 0.71073 8.2027 8.8661 11.4800 89.566 70.547 81.668 ZERR 2.00 0.0006 0.0005 0.0007 0.005 0.006 0.006 LATT 1 SFAC C H I N CL UNIT 20 20 6 4 2 MERG 2 omit -4 54 acta FMAP 2 PLAN 20 BOND LIST 6 L.S. 10 WGHT 0.055400 FVAR 4.44899 I1 3 0.530668 -0.012590 0.267977 11.00000 0.05148 0.05114 = 0.05502 -0.00956 -0.02485 -0.00027 I2 3 0.362121 0.481715 0.825122 11.00000 0.04171 0.06055 = 0.05768 -0.00754 -0.01967 0.00231 I3 3 0.293430 -0.214847 0.146697 11.00000 0.04755 0.06598 = 0.07472 -0.02390 -0.03320 0.00855 CL1 5 0.226889 0.347311 0.522200 11.00000 0.03598 0.06963 = 0.07054 -0.02647 -0.02091 0.00365 N1 4 0.606007 0.205622 0.433002 11.00000 0.03128 0.04519 = 0.04339 -0.00273 -0.01351 -0.00472 AFIX 43 H1 2 0.497611 0.238777 0.444900 11.00000 -1.20000 AFIX 0 N2 4 0.038100 0.542517 0.759610 11.00000 0.03996 0.05334 = 0.04717 -0.00262 -0.01840 0.00191 AFIX 43 H2 2 0.095430 0.471028 0.704962 11.00000 -1.20000 AFIX 0 C1 1 0.682636 0.085151 0.355454 11.00000 0.04236 0.03619 = 0.04377 0.00603 -0.01832 -0.00645 C2 1 0.854749 0.033923 0.330731 11.00000 0.04431 0.04402 = 0.05407 -0.00731 -0.01860 0.00681 AFIX 43 H2A 2 0.911147 -0.047191 0.274040 11.00000 -1.20000 AFIX 0 C10 1 -0.122595 0.598503 0.769129 11.00000 0.05027 0.06706 = 0.05418 0.00802 -0.02624 -0.00297 AFIX 43 H10 2 -0.172366 0.558930 0.716437 11.00000 -1.20000 AFIX 0 C5 1 0.685148 0.275143 0.491095 11.00000 0.03938 0.05250 = 0.05240 -0.01451 -0.01343 -0.00285 AFIX 43 H5 2 0.626343 0.358429 0.544919 11.00000 -1.20000 AFIX 0 C6 1 0.111396 0.593931 0.831827 11.00000 0.04280 0.04351 = 0.04607 0.00347 -0.01059 0.00352 C3 1 0.941599 0.101614 0.388912 11.00000 0.03159 0.06851 = 0.06903 0.01682 -0.01162 0.00285 AFIX 43 H3 2 1.059598 0.066571 0.373683 11.00000 -1.20000 AFIX 0 C9 1 -0.219187 0.711488 0.852408 11.00000 0.04925 0.08009 = 0.05743 0.00411 -0.02092 0.00545 AFIX 43 H9 2 -0.333536 0.748388 0.857531 11.00000 -1.20000 AFIX 0 C8 1 -0.149398 0.766990 0.924574 11.00000 0.06050 0.07650 = 0.04365 -0.00425 -0.00571 0.01879 AFIX 43 H8 2 -0.213555 0.846103 0.981317 11.00000 -1.20000 AFIX 0 C4 1 0.859066 0.223105 0.471550 11.00000 0.05808 0.07548 = 0.06592 0.00747 -0.02845 -0.03245 AFIX 43 H4 2 0.919626 0.269165 0.513387 11.00000 -1.20000 AFIX 0 C7 1 0.022202 0.709787 0.918839 11.00000 0.06565 0.05768 = 0.04769 -0.01823 -0.01400 0.00149 AFIX 43 H7 2 0.073136 0.748272 0.971252 11.00000 -1.20000 AFIX 0 HKLF 4 REM shelxt_a.res in P-1 REM wR2 = 0.1126, GooF = S = 0.921, Restrained GooF = 0.921 for all data REM R1 = 0.0414 for 2243 Fo > 4sig(Fo) and 0.0647 for all 3374 data REM 145 parameters refined using 0 restraints END WGHT 0.0562 0.0000 REM Highest difference peak 0.662, deepest hole -1.182, 1-sigma level 0.182 Q1 1 0.4345 0.4340 0.5649 11.00000 0.05 0.66 Q2 1 0.5519 0.0752 0.2254 11.00000 0.05 0.66 Q3 1 0.2727 -0.0762 0.1388 11.00000 0.05 0.65 Q4 1 0.3148 -0.3045 0.1377 11.00000 0.05 0.63 Q5 1 0.4065 -0.0140 0.3649 11.00000 0.05 0.62 Q6 1 0.4140 -0.3317 0.0235 11.00000 0.05 0.61 Q7 1 0.6694 0.0838 0.3269 11.00000 0.05 0.61 Q8 1 0.1914 -0.2070 0.2274 11.00000 0.05 0.57 Q9 1 0.2359 -0.4047 0.1338 11.00000 0.05 0.57 Q10 1 -0.1383 0.5855 0.7346 11.00000 0.05 0.57 Q11 1 0.4916 0.0609 0.2950 11.00000 0.05 0.56 Q12 1 -0.1162 0.7791 0.9373 11.00000 0.05 0.55 Q13 1 0.4729 0.2772 0.5893 11.00000 0.05 0.54 Q14 1 0.4278 -0.2089 0.0433 11.00000 0.05 0.54 Q15 1 -0.2832 0.4686 0.7123 11.00000 0.05 0.54 Q16 1 0.4982 0.4396 0.4212 11.00000 0.05 0.51 Q17 1 0.3700 0.5841 0.8063 11.00000 0.05 0.51 Q18 1 -0.2628 0.7018 1.0681 11.00000 0.05 0.51 Q19 1 0.6757 -0.1223 0.3130 11.00000 0.05 0.51 Q20 1 0.9533 0.0868 0.4209 11.00000 0.05 0.50 ; _shelx_res_checksum 55896 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' 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 I1 I 0.53067(7) -0.01259(6) 0.26798(5) 0.05151(18) Uani 1 1 d . . . . . I2 I 0.36212(7) 0.48172(6) 0.82512(5) 0.05355(18) Uani 1 1 d . . . . . I3 I 0.29343(8) -0.21485(7) 0.14670(6) 0.0612(2) Uani 1 1 d . . . . . Cl1 Cl 0.2269(3) 0.3473(2) 0.5222(2) 0.0590(5) Uani 1 1 d . . . . . N1 N 0.6060(8) 0.2056(7) 0.4330(5) 0.0398(13) Uani 1 1 d . . . . . H1 H 0.497611 0.238777 0.444900 0.048 Uiso 1 1 calc R U . . . N2 N 0.0381(9) 0.5425(7) 0.7596(6) 0.0468(15) Uani 1 1 d . . . . . H2 H 0.095430 0.471028 0.704962 0.056 Uiso 1 1 calc R U . . . C1 C 0.6826(10) 0.0852(8) 0.3555(7) 0.0398(16) Uani 1 1 d . . . . . C2 C 0.8547(11) 0.0339(9) 0.3307(7) 0.0483(19) Uani 1 1 d . . . . . H2A H 0.911147 -0.047191 0.274040 0.058 Uiso 1 1 calc R U . . . C10 C -0.1226(12) 0.5985(10) 0.7691(8) 0.056(2) Uani 1 1 d . . . . . H10 H -0.172366 0.558930 0.716437 0.067 Uiso 1 1 calc R U . . . C5 C 0.6851(11) 0.2751(9) 0.4911(7) 0.0489(19) Uani 1 1 d . . . . . H5 H 0.626343 0.358429 0.544919 0.059 Uiso 1 1 calc R U . . . C6 C 0.1114(11) 0.5939(8) 0.8318(7) 0.0463(18) Uani 1 1 d . . . . . C3 C 0.9416(11) 0.1016(10) 0.3889(8) 0.059(2) Uani 1 1 d . . . . . H3 H 1.059598 0.066571 0.373683 0.071 Uiso 1 1 calc R U . . . C9 C -0.2192(13) 0.7115(10) 0.8524(8) 0.063(2) Uani 1 1 d . . . . . H9 H -0.333536 0.748388 0.857531 0.076 Uiso 1 1 calc R U . . . C8 C -0.1494(13) 0.7670(11) 0.9246(8) 0.066(3) Uani 1 1 d . . . . . H8 H -0.213555 0.846103 0.981317 0.079 Uiso 1 1 calc R U . . . C4 C 0.8591(13) 0.2231(11) 0.4716(8) 0.062(2) Uani 1 1 d . . . . . H4 H 0.919626 0.269165 0.513387 0.075 Uiso 1 1 calc R U . . . C7 C 0.0222(13) 0.7098(9) 0.9188(7) 0.059(2) Uani 1 1 d . . . . . H7 H 0.073136 0.748272 0.971252 0.071 Uiso 1 1 calc R U . . . 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 0.0515(3) 0.0511(3) 0.0550(3) -0.0096(2) -0.0248(3) -0.0003(2) I2 0.0417(3) 0.0606(3) 0.0577(3) -0.0075(2) -0.0197(3) 0.0023(2) I3 0.0475(3) 0.0660(4) 0.0747(4) -0.0239(3) -0.0332(3) 0.0085(3) Cl1 0.0360(10) 0.0696(13) 0.0705(14) -0.0265(10) -0.0209(10) 0.0036(10) N1 0.031(3) 0.045(3) 0.043(3) -0.003(3) -0.014(3) -0.005(3) N2 0.040(4) 0.053(4) 0.047(4) -0.003(3) -0.018(3) 0.002(3) C1 0.042(4) 0.036(4) 0.044(4) 0.006(3) -0.018(3) -0.006(3) C2 0.044(5) 0.044(4) 0.054(5) -0.007(3) -0.019(4) 0.007(4) C10 0.050(5) 0.067(5) 0.054(5) 0.008(4) -0.026(4) -0.003(4) C5 0.039(5) 0.052(5) 0.052(5) -0.015(4) -0.013(4) -0.003(4) C6 0.043(5) 0.044(4) 0.046(4) 0.003(3) -0.011(4) 0.004(4) C3 0.032(4) 0.069(6) 0.069(6) 0.017(5) -0.012(4) 0.003(4) C9 0.049(5) 0.080(6) 0.057(5) 0.004(5) -0.021(5) 0.005(5) C8 0.060(6) 0.077(6) 0.044(5) -0.004(4) -0.006(4) 0.019(5) C4 0.058(6) 0.075(6) 0.066(6) 0.007(5) -0.028(5) -0.032(5) C7 0.066(6) 0.058(5) 0.048(5) -0.018(4) -0.014(4) 0.001(5) 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' I I -0.4742 1.8119 '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' Cl Cl 0.1484 0.1585 '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 C5 N1 C1 123.7(7) . . ? C6 N2 C10 120.5(8) . . ? N1 C1 C2 119.7(7) . . ? N1 C1 I1 118.0(5) . . ? C2 C1 I1 122.2(6) . . ? C3 C2 C1 118.7(8) . . ? N2 C10 C9 122.7(9) . . ? N1 C5 C4 118.3(8) . . ? N2 C6 C7 120.5(8) . . ? N2 C6 I2 118.5(6) . . ? C7 C6 I2 120.7(7) . . ? C4 C3 C2 120.8(8) . . ? C8 C9 C10 118.5(9) . . ? C9 C8 C7 121.0(9) . . ? C3 C4 C5 118.7(8) . . ? C6 C7 C8 116.8(9) . . ? 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 I1 C1 2.115(7) . ? I2 C6 2.128(8) . ? N1 C5 1.287(9) . ? N1 C1 1.333(9) . ? N2 C6 1.294(10) . ? N2 C10 1.308(10) . ? C1 C2 1.352(11) . ? C2 C3 1.327(11) . ? C10 C9 1.351(12) . ? C5 C4 1.377(12) . ? C6 C7 1.378(11) . ? C3 C4 1.377(13) . ? C9 C8 1.288(12) . ? C8 C7 1.405(13) . ?