#------------------------------------------------------------------------------ #$Date: 2020-05-13 04:35:15 +0300 (Wed, 13 May 2020) $ #$Revision: 252006 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/05/7240504.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_7240504 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 'C5 H5 Cl I N' _chemical_formula_weight 241.45 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 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 90 _cell_angle_beta 94.886(7) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 4.4564(3) _cell_length_b 10.8438(7) _cell_length_c 14.8824(11) _cell_measurement_reflns_used 1443 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 38.2095 _cell_measurement_theta_min 3.9931 _cell_volume 716.57(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 ; G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr., 2008, 64, 112-122. ; _diffrn_ambient_temperature 298(2) _diffrn_detector_area_resol_mean 16.3426 _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.993 _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 0.1385 _diffrn_reflns_av_unetI/netI 0.1139 _diffrn_reflns_Laue_measured_fraction_full 0.992 _diffrn_reflns_Laue_measured_fraction_max 0.993 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 5186 _diffrn_reflns_point_group_measured_fraction_full 0.992 _diffrn_reflns_point_group_measured_fraction_max 0.993 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.991 _diffrn_reflns_theta_min 4.002 _diffrn_source 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 4.738 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.13277 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 2.238 _exptl_crystal_description block _exptl_crystal_F_000 448 _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.22 _refine_diff_density_max 0.885 _refine_diff_density_min -0.653 _refine_diff_density_rms 0.131 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.800 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 73 _refine_ls_number_reflns 1550 _refine_ls_number_restraints 20 _refine_ls_restrained_S_all 0.797 _refine_ls_R_factor_all 0.0883 _refine_ls_R_factor_gt 0.0413 _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^)+(0.0155P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0748 _refine_ls_wR_factor_ref 0.0836 _reflns_Friedel_coverage 0.000 _reflns_number_gt 883 _reflns_number_total 1550 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ce00534g2.cif _cod_data_source_block 2-IPyHCl _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 7240504 _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 SIR92 run in space group P 21/n shelx.res created by SHELXL-2018/3 at 14:31:49 on 15-Oct-2019 CELL 0.71073 4.4564 10.8438 14.8824 90.000 94.886 90.000 ZERR 4.00 0.0003 0.0007 0.0011 0.000 0.007 0.000 LATT 1 SYMM 1/2 - X, 1/2 + Y, 1/2 - Z SFAC C H N CL I UNIT 20 20 4 4 4 MERG 2 OMIT -4.00 54.00 OMIT -1 0 3 OMIT 0 0 10 OMIT 2 1 15 OMIT 3 1 0 OMIT -1 0 9 OMIT 1 1 12 SIMU 0.040 0.080 1.700 C4 C3 C6 C5 DELU 0.010 0.010 C6 C5 DELU 0.010 0.010 C4 C5 FMAP 2 PLAN 25 ACTA BOND $H CONF L.S. 50 TEMP 25.00 WGHT 0.015500 FVAR 3.13228 I1 5 0.553983 -0.037344 0.857874 11.00000 0.06294 0.05637 = 0.05383 -0.00166 -0.01432 0.00055 CL1 4 0.064563 0.181388 0.672682 11.00000 0.08267 0.05920 = 0.06341 0.00092 -0.02735 -0.00196 N1 3 0.520375 0.235174 0.828092 11.00000 0.06311 0.06054 = 0.04011 0.00146 -0.01467 -0.00103 AFIX 43 H1 2 0.393098 0.212828 0.784445 11.00000 -1.20000 AFIX 0 C4 1 0.911249 0.307344 0.965241 11.00000 0.11449 0.05592 = 0.06699 -0.00202 -0.02871 -0.01223 AFIX 43 H4 2 1.039500 0.332536 1.014381 11.00000 -1.20000 AFIX 0 C2 1 0.659747 0.147432 0.881965 11.00000 0.05590 0.04940 = 0.04723 0.00898 -0.00243 0.01408 C3 1 0.857771 0.184529 0.951089 11.00000 0.06668 0.06569 = 0.05801 -0.00143 -0.02181 0.00232 AFIX 43 H3 2 0.956890 0.126375 0.988760 11.00000 -1.20000 AFIX 0 C6 1 0.575095 0.353231 0.840982 11.00000 0.08749 0.06418 = 0.05002 0.00593 -0.00909 0.00790 AFIX 43 H6 2 0.472219 0.410461 0.803372 11.00000 -1.20000 AFIX 0 C5 1 0.777609 0.393902 0.907671 11.00000 0.09836 0.06550 = 0.07710 -0.00286 -0.01258 -0.01997 AFIX 43 H5 2 0.824030 0.477222 0.914107 11.00000 -1.20000 AFIX 0 HKLF 4 REM SIR92 run in space group P 21/n REM wR2 = 0.0836, GooF = S = 0.800, Restrained GooF = 0.797 for all data REM R1 = 0.0413 for 883 Fo > 4sig(Fo) and 0.0883 for all 1550 data REM 73 parameters refined using 20 restraints END WGHT 0.0155 0.0000 REM Highest difference peak 0.885, deepest hole -0.653, 1-sigma level 0.131 Q1 1 0.4546 -0.0346 0.7971 11.00000 0.05 0.89 Q2 1 0.6659 -0.0374 0.9167 11.00000 0.05 0.83 Q3 1 0.5466 -0.1254 0.8610 11.00000 0.05 0.69 Q4 1 0.5489 0.0662 0.8605 11.00000 0.05 0.59 Q5 1 0.2195 -0.0409 0.8827 11.00000 0.05 0.58 Q6 1 0.3164 -0.0369 0.9429 11.00000 0.05 0.51 Q7 1 0.0519 0.2738 0.6780 11.00000 0.05 0.50 Q8 1 1.2430 0.1382 1.0401 11.00000 0.05 0.39 Q9 1 0.6159 -0.0378 0.8485 11.00000 0.05 0.38 Q10 1 0.8915 -0.0339 0.8387 11.00000 0.05 0.36 Q11 1 0.2667 0.1924 0.6387 11.00000 0.05 0.36 Q12 1 1.0105 -0.0351 0.8423 11.00000 0.05 0.35 Q13 1 0.9422 0.3998 0.8006 11.00000 0.05 0.35 Q14 1 0.7272 0.2096 0.9621 11.00000 0.05 0.35 Q15 1 0.4857 0.1314 0.8197 11.00000 0.05 0.33 Q16 1 0.7032 0.0150 0.9847 11.00000 0.05 0.33 Q17 1 0.6661 0.2109 0.8771 11.00000 0.05 0.31 Q18 1 0.3949 0.5319 0.8798 11.00000 0.05 0.31 Q19 1 0.1557 0.3352 0.7729 11.00000 0.05 0.31 Q20 1 -0.1124 0.1828 0.6011 11.00000 0.05 0.30 Q21 1 0.4062 0.0057 0.7410 11.00000 0.05 0.30 Q22 1 0.6996 0.5417 0.8545 11.00000 0.05 0.30 Q23 1 0.4028 0.1661 0.9635 11.00000 0.05 0.30 Q24 1 0.1851 0.3732 0.7402 11.00000 0.05 0.30 Q25 1 0.6060 0.4591 0.7248 11.00000 0.05 0.30 ; _shelx_res_checksum 5861 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -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 I1 I 0.55398(10) -0.03734(5) 0.85787(3) 0.05882(19) Uani 1 1 d . . . . . Cl1 Cl 0.0646(5) 0.18139(17) 0.67268(11) 0.0703(6) Uani 1 1 d . . . . . N1 N 0.5204(13) 0.2352(6) 0.8281(3) 0.0557(16) Uani 1 1 d . . . . . H1 H 0.393098 0.212828 0.784445 0.067 Uiso 1 1 calc R U . . . C4 C 0.9112(19) 0.3073(8) 0.9652(5) 0.081(3) Uani 1 1 d . U . . . H4 H 1.039500 0.332536 1.014381 0.097 Uiso 1 1 calc R U . . . C2 C 0.6597(15) 0.1474(6) 0.8820(4) 0.0512(18) Uani 1 1 d . . . . . C3 C 0.8578(15) 0.1845(7) 0.9511(4) 0.065(2) Uani 1 1 d . U . . . H3 H 0.956890 0.126375 0.988760 0.078 Uiso 1 1 calc R U . . . C6 C 0.5751(17) 0.3532(8) 0.8410(4) 0.068(2) Uani 1 1 d . U . . . H6 H 0.472219 0.410461 0.803372 0.082 Uiso 1 1 calc R U . . . C5 C 0.7776(18) 0.3939(8) 0.9077(5) 0.081(2) Uani 1 1 d . U . . . H5 H 0.824030 0.477222 0.914107 0.098 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 0.0629(3) 0.0564(3) 0.0538(3) -0.0017(2) -0.0143(2) 0.0005(3) Cl1 0.0827(14) 0.0592(13) 0.0634(11) 0.0009(10) -0.0273(9) -0.0020(11) N1 0.063(4) 0.061(4) 0.040(3) 0.001(3) -0.015(3) -0.001(3) C4 0.114(7) 0.056(5) 0.067(5) -0.002(4) -0.029(4) -0.012(5) C2 0.056(4) 0.049(5) 0.047(4) 0.009(3) -0.002(3) 0.014(4) C3 0.067(5) 0.066(6) 0.058(4) -0.001(4) -0.022(4) 0.002(4) C6 0.087(6) 0.064(6) 0.050(5) 0.006(4) -0.009(4) 0.008(4) C5 0.098(6) 0.065(5) 0.077(5) -0.003(5) -0.013(4) -0.020(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' 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' I I -0.4742 1.8119 '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 121.7(6) . . ? C6 N1 H1 119.1 . . ? C2 N1 H1 119.1 . . ? C3 C4 C5 120.7(7) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C3 C2 N1 118.3(7) . . ? C3 C2 I1 122.6(5) . . ? N1 C2 I1 119.1(5) . . ? C2 C3 C4 119.9(7) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? N1 C6 C5 121.8(7) . . ? N1 C6 H6 119.1 . . ? C5 C6 H6 119.1 . . ? C6 C5 C4 117.4(8) . . ? C6 C5 H5 121.3 . . ? C4 C5 H5 121.3 . . ? 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 C2 2.082(7) . ? N1 C6 1.314(9) . ? N1 C2 1.360(8) . ? N1 H1 0.8600 . ? C4 C3 1.366(10) . ? C4 C5 1.372(10) . ? C4 H4 0.9300 . ? C2 C3 1.358(8) . ? C3 H3 0.9300 . ? C6 C5 1.357(8) . ? C6 H6 0.9300 . ? C5 H5 0.9300 . ? 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 C6 N1 C2 C3 0.6(10) . . . . ? C6 N1 C2 I1 179.0(5) . . . . ? N1 C2 C3 C4 0.3(11) . . . . ? I1 C2 C3 C4 -178.0(6) . . . . ? C5 C4 C3 C2 -3.1(13) . . . . ? C2 N1 C6 C5 1.2(12) . . . . ? N1 C6 C5 C4 -3.9(13) . . . . ? C3 C4 C5 C6 4.8(14) . . . . ?