#------------------------------------------------------------------------------ #$Date: 2020-05-13 04:35:15 +0300 (Wed, 13 May 2020) $ #$Revision: 252006 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/05/7240508.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_7240508 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_moiety 'C5 H5 I N, Cl' _chemical_formula_sum 'C5 H5 Cl I N' _chemical_formula_weight 241.45 _space_group_crystal_system monoclinic _space_group_IT_number 11 _space_group_name_Hall '-P 2yb' _space_group_name_H-M_alt 'P 1 21/m 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 94.120(18) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 4.3369(8) _cell_length_b 8.4079(17) _cell_length_c 9.736(2) _cell_measurement_reflns_used 899 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 32.7105 _cell_measurement_theta_min 4.1998 _cell_volume 354.10(12) _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 293(2) _diffrn_detector_area_resol_mean 16.3426 _diffrn_measured_fraction_theta_full 0.983 _diffrn_measured_fraction_theta_max 0.979 _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 0.0668 _diffrn_reflns_av_unetI/netI 0.0699 _diffrn_reflns_Laue_measured_fraction_full 0.983 _diffrn_reflns_Laue_measured_fraction_max 0.979 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 1860 _diffrn_reflns_point_group_measured_fraction_full 0.983 _diffrn_reflns_point_group_measured_fraction_max 0.979 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.988 _diffrn_reflns_theta_min 4.197 _diffrn_source 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 4.794 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.11855 _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 2.265 _exptl_crystal_description needle _exptl_crystal_F_000 224 _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.12 _refine_diff_density_max 3.451 _refine_diff_density_min -1.548 _refine_diff_density_rms 0.292 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 44 _refine_ls_number_reflns 810 _refine_ls_number_restraints 21 _refine_ls_restrained_S_all 1.075 _refine_ls_R_factor_all 0.0968 _refine_ls_R_factor_gt 0.0811 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1306P)^2^+2.4460P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2208 _refine_ls_wR_factor_ref 0.2298 _reflns_Friedel_coverage 0.000 _reflns_number_gt 605 _reflns_number_total 810 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ce00534g2.cif _cod_data_source_block 4-IPyHCl _cod_original_sg_symbol_H-M 'P 21/m' _cod_database_code 7240508 _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 P2(1)/m shelx.res created by SHELXL-2018/3 at 13:54:35 on 15-Oct-2019 CELL 0.71073 4.3369 8.4079 9.7361 90.000 94.120 90.000 ZERR 2.00 0.0008 0.0017 0.0020 0.000 0.018 0.000 LATT 1 SYMM - X, 1/2 + Y, - Z SFAC C H N CL I UNIT 10 10 2 2 2 MERG 2 OMIT -4.00 54.00 OMIT 3 2 3 OMIT 3 1 1 OMIT 3 3 1 OMIT -3 2 3 OMIT -3 0 3 OMIT -3 4 3 OMIT 3 3 2 TWIN -1.00 0.00 0.00 0.00 -1.00 0.00 0.32 0.00 1.00 2 DELU 0.010 0.010 C3 C2 SIMU 0.040 0.080 1.700 C3 C2 ISOR 0.100 C4 N1 DFIX 1.373 0.0000020 C4 C3 DANG 2.357 0.0000020 C4 C2 FMAP 2 PLAN 20 ACTA BOND LIST 6 L.S. 40 WGHT 0.130600 2.446000 BASF 0.00136 FVAR 7.05278 I1 5 0.142276 0.750000 0.543234 10.50000 0.04753 0.05152 = 0.05175 0.00000 0.01243 0.00000 CL1 4 -0.013018 0.750000 0.864680 10.50000 0.05942 0.05783 = 0.04421 0.00000 0.02186 0.00000 C4 1 0.349235 0.750000 0.353731 10.50000 0.04712 0.04050 = 0.04019 0.00000 0.01686 0.00000 N1 3 0.628809 0.750000 0.117021 10.50000 0.04679 0.08588 = 0.03773 0.00000 0.01131 0.00000 AFIX 43 H1 2 0.729148 0.749999 0.043976 10.50000 -1.20000 AFIX 0 C3 1 0.394254 0.608096 0.288315 11.00000 0.07012 0.03797 = 0.05762 -0.00089 0.00035 -0.01100 AFIX 43 H3 2 0.318960 0.513317 0.322041 11.00000 -1.20000 AFIX 0 C2 1 0.554462 0.610493 0.171146 11.00000 0.07594 0.05518 = 0.05105 -0.00691 0.00311 0.00443 AFIX 43 H2 2 0.610255 0.515843 0.130169 11.00000 -1.20000 AFIX 0 HKLF 4 REM shelxt_a.res in P2(1)/m REM wR2 = 0.2298, GooF = S = 1.089, Restrained GooF = 1.075 for all data REM R1 = 0.0811 for 605 Fo > 4sig(Fo) and 0.0968 for all 810 data REM 44 parameters refined using 21 restraints END WGHT 0.1307 2.5141 REM Highest difference peak 3.451, deepest hole -1.548, 1-sigma level 0.292 Q1 1 0.4827 0.7500 0.5503 10.50000 0.05 3.45 Q2 1 -0.1800 0.7500 0.5412 10.50000 0.05 3.41 Q3 1 0.0884 0.7500 0.3773 10.50000 0.05 1.51 Q4 1 0.2712 0.8374 0.5995 11.00000 0.05 1.26 Q5 1 -0.0127 0.8222 0.4804 11.00000 0.05 1.09 Q6 1 0.7528 0.7500 0.3746 10.50000 0.05 1.05 Q7 1 0.1058 0.7500 0.9366 10.50000 0.05 0.93 Q8 1 0.3504 0.7500 0.4404 10.50000 0.05 0.92 Q9 1 0.8338 0.7500 0.0328 10.50000 0.05 0.86 Q10 1 0.1861 0.7500 1.0387 10.50000 0.05 0.84 Q11 1 0.3715 0.7500 0.8854 10.50000 0.05 0.74 Q12 1 -0.1233 0.7500 0.8432 10.50000 0.05 0.73 Q13 1 -0.2956 0.7500 0.8680 10.50000 0.05 0.66 Q14 1 -0.2645 0.7500 0.7482 10.50000 0.05 0.64 Q15 1 0.0230 0.7978 0.7478 11.00000 0.05 0.62 Q16 1 0.1572 0.8341 0.6483 11.00000 0.05 0.60 Q17 1 0.5078 0.7500 0.2382 10.50000 0.05 0.59 Q18 1 0.1862 0.7500 0.2149 10.50000 0.05 0.58 Q19 1 0.5178 0.7500 0.0281 10.50000 0.05 0.55 Q20 1 -0.0632 0.7500 0.6599 10.50000 0.05 0.53 ; _shelx_res_checksum 87647 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, 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 0.1423(3) 0.750000 0.54323(13) 0.0498(6) Uani 1 2 d S T P . . Cl1 Cl -0.0130(13) 0.750000 0.8647(5) 0.0529(13) Uani 1 2 d S T P . . C4 C 0.34924(3) 0.750000 0.35373(2) 0.042(4) Uani 1 2 d DS TU P . . N1 N 0.629(4) 0.750000 0.1170(18) 0.056(5) Uani 1 2 d S TU P . . H1 H 0.729148 0.749999 0.043976 0.068 Uiso 1 2 calc R U P . . C3 C 0.39425(9) 0.60810(2) 0.28832(2) 0.055(3) Uani 1 1 d D U . . . H3 H 0.318960 0.513317 0.322041 0.067 Uiso 1 1 calc R U . . . C2 C 0.55446(4) 0.61049(2) 0.17115(2) 0.061(4) Uani 1 1 d D U . . . H2 H 0.610255 0.515843 0.130169 0.073 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 0.0475(8) 0.0515(9) 0.0518(9) 0.000 0.0124(6) 0.000 Cl1 0.059(3) 0.058(3) 0.044(3) 0.000 0.022(2) 0.000 C4 0.047(10) 0.041(9) 0.040(9) 0.000 0.017(8) 0.000 N1 0.047(9) 0.086(14) 0.038(9) 0.000 0.011(7) 0.000 C3 0.070(9) 0.038(8) 0.058(8) -0.001(6) 0.000(7) -0.011(7) C2 0.076(10) 0.055(10) 0.051(7) -0.007(7) 0.003(7) 0.004(8) 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 C3 C4 C3 120.682(19) . 4_575 ? C3 C4 I1 119.305(11) . . ? C3 C4 I1 119.304(11) 4_575 . ? C2 N1 C2 123.0(13) 4_575 . ? C4 C3 C2 117.925(15) . . ? N1 C2 C3 119.4(6) . . ? 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 C4 2.1090(13) . ? C4 C3 1.3730(2) . ? C4 C3 1.3730(2) 4_575 ? N1 C2 1.335(8) 4_575 ? N1 C2 1.335(8) . ? C3 C2 1.3778(3) . ?