#------------------------------------------------------------------------------ #$Date: 2020-05-13 04:35:15 +0300 (Wed, 13 May 2020) $ #$Revision: 252006 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/05/7240506.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_7240506 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 I2 N' _chemical_formula_weight 332.90 _space_group_crystal_system orthorhombic _space_group_IT_number 29 _space_group_name_Hall 'P 2c -2ac' _space_group_name_H-M_alt 'P c a 21' _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 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 15.0849(7) _cell_length_b 4.7247(2) _cell_length_c 11.2538(4) _cell_measurement_reflns_used 4246 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 36.2759 _cell_measurement_theta_min 3.8616 _cell_volume 802.08(6) _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 'SHELXS-2018/3 (Sheldrick, 2018)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 16.3426 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.997 _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 0.0294 _diffrn_reflns_av_unetI/netI 0.0248 _diffrn_reflns_Laue_measured_fraction_full 0.996 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 6146 _diffrn_reflns_point_group_measured_fraction_full 0.971 _diffrn_reflns_point_group_measured_fraction_max 0.973 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.999 _diffrn_reflns_theta_min 4.314 _diffrn_source 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 7.750 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.60257 _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 yellow _exptl_crystal_density_diffrn 2.757 _exptl_crystal_description block _exptl_crystal_F_000 592 _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.22 _refine_diff_density_max 0.502 _refine_diff_density_min -0.478 _refine_diff_density_rms 0.089 _refine_ls_abs_structure_details ; Flack x determined using 657 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.08(4) _refine_ls_extinction_coef 0.0261(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2018/3 (Sheldrick 2018)' _refine_ls_goodness_of_fit_ref 0.871 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 74 _refine_ls_number_reflns 1695 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 0.871 _refine_ls_R_factor_all 0.0232 _refine_ls_R_factor_gt 0.0191 _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^)+(0.0282P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0413 _refine_ls_wR_factor_ref 0.0422 _reflns_Friedel_coverage 0.852 _reflns_Friedel_fraction_full 0.943 _reflns_Friedel_fraction_max 0.947 _reflns_number_gt 1538 _reflns_number_total 1695 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ce00534g2.cif _cod_data_source_block 2-IPyHI _cod_database_code 7240506 _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 Pca2(1) shelx.res created by SHELXL-2018/3 at 14:55:00 on 26-Jun-2019 CELL 0.71073 15.0849 4.7247 11.2538 90.000 90.000 90.000 ZERR 4.00 0.0007 0.0002 0.0004 0.000 0.000 0.000 LATT -1 SYMM - X, - Y, 1/2 + Z SYMM 1/2 + X, - Y, Z SYMM 1/2 - X, Y, 1/2 + Z SFAC C H N I UNIT 20 20 4 8 MERG 2 OMIT -4.00 54.00 FMAP 2 PLAN 20 ACTA BOND LIST 6 L.S. 20 WGHT 0.028200 EXTI 0.026058 FVAR 4.59412 I1 4 0.375387 0.711737 0.706634 11.00000 0.04653 0.05633 = 0.03997 -0.00365 0.00231 0.00086 I2 4 0.599447 1.129524 0.505544 11.00000 0.04857 0.04567 = 0.04121 0.00227 -0.00169 -0.00545 C2 1 0.366597 0.582202 0.528878 11.00000 0.03486 0.04346 = 0.03935 0.00256 -0.00241 0.00998 C3 1 0.306538 0.386580 0.490497 11.00000 0.03812 0.05199 = 0.04923 0.00218 -0.00294 -0.00435 AFIX 43 H3 2 0.265636 0.308352 0.542887 11.00000 -1.20000 AFIX 0 N1 3 0.424035 0.694862 0.451057 11.00000 0.03786 0.04174 = 0.04147 -0.00240 0.00005 0.00065 AFIX 43 H1 2 0.462392 0.815874 0.475862 11.00000 -1.20000 AFIX 0 C4 1 0.307598 0.305767 0.370847 11.00000 0.05420 0.05127 = 0.05221 -0.00063 -0.01395 -0.00513 AFIX 43 H4 2 0.268328 0.168797 0.343432 11.00000 -1.20000 AFIX 0 C5 1 0.366866 0.429510 0.294018 11.00000 0.05464 0.06081 = 0.04137 -0.00858 -0.00948 0.00888 AFIX 43 H5 2 0.367694 0.378630 0.214195 11.00000 -1.20000 AFIX 0 C6 1 0.423266 0.623810 0.335478 11.00000 0.04993 0.05574 = 0.03911 -0.00259 0.00775 0.00275 AFIX 43 H6 2 0.462613 0.711260 0.283521 11.00000 -1.20000 AFIX 0 HKLF 4 REM shelxt_a.res in Pca2(1) REM wR2 = 0.0422, GooF = S = 0.871, Restrained GooF = 0.871 for all data REM R1 = 0.0191 for 1538 Fo > 4sig(Fo) and 0.0232 for all 1695 data REM 74 parameters refined using 1 restraints END WGHT 0.0212 0.0000 REM Highest difference peak 0.502, deepest hole -0.478, 1-sigma level 0.089 Q1 1 0.4344 0.7197 0.7026 11.00000 0.05 0.50 Q2 1 0.6678 1.1388 0.5104 11.00000 0.05 0.37 Q3 1 0.3033 0.7416 0.7015 11.00000 0.05 0.36 Q4 1 0.3770 1.0395 0.7036 11.00000 0.05 0.36 Q5 1 0.5328 1.1215 0.5123 11.00000 0.05 0.29 Q6 1 0.6781 1.4104 0.5075 11.00000 0.05 0.28 Q7 1 0.5941 0.6613 0.5055 11.00000 0.05 0.28 Q8 1 0.3317 0.3028 0.7092 11.00000 0.05 0.28 Q9 1 0.4920 1.2002 0.5192 11.00000 0.05 0.27 Q10 1 0.5574 0.9133 0.2044 11.00000 0.05 0.26 Q11 1 0.2015 0.1096 0.5102 11.00000 0.05 0.26 Q12 1 0.2779 0.5093 0.7006 11.00000 0.05 0.25 Q13 1 0.3890 0.2869 0.4801 11.00000 0.05 0.25 Q14 1 0.5223 1.3868 0.5144 11.00000 0.05 0.25 Q15 1 0.7138 1.2572 0.4604 11.00000 0.05 0.25 Q16 1 0.2877 0.9496 0.7034 11.00000 0.05 0.24 Q17 1 0.3982 0.3214 0.2194 11.00000 0.05 0.24 Q18 1 0.3973 0.3211 0.5634 11.00000 0.05 0.23 Q19 1 0.3727 0.1989 0.1598 11.00000 0.05 0.23 Q20 1 0.1174 0.2487 0.3411 11.00000 0.05 0.23 ; _shelx_res_checksum 60330 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, 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 0.37539(3) 0.71174(10) 0.70663(5) 0.04761(15) Uani 1 1 d . . . . . I2 I 0.59945(3) 1.12952(9) 0.50554(5) 0.04515(15) Uani 1 1 d . . . . . C2 C 0.3666(4) 0.5822(14) 0.5289(6) 0.0392(14) Uani 1 1 d . . . . . C3 C 0.3065(4) 0.3866(13) 0.4905(8) 0.0464(15) Uani 1 1 d . . . . . H3 H 0.265636 0.308352 0.542887 0.056 Uiso 1 1 calc R U . . . N1 N 0.4240(4) 0.6949(11) 0.4511(5) 0.0404(12) Uani 1 1 d . . . . . H1 H 0.462392 0.815874 0.475862 0.048 Uiso 1 1 calc R U . . . C4 C 0.3076(5) 0.3058(17) 0.3708(7) 0.0526(18) Uani 1 1 d . . . . . H4 H 0.268328 0.168797 0.343432 0.063 Uiso 1 1 calc R U . . . C5 C 0.3669(5) 0.4295(17) 0.2940(7) 0.0523(17) Uani 1 1 d . . . . . H5 H 0.367694 0.378630 0.214195 0.063 Uiso 1 1 calc R U . . . C6 C 0.4233(5) 0.6238(16) 0.3355(6) 0.0483(17) Uani 1 1 d . . . . . H6 H 0.462613 0.711260 0.283521 0.058 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 0.0465(2) 0.0563(3) 0.0400(2) -0.0036(3) 0.0023(3) 0.0009(2) I2 0.0486(2) 0.0457(2) 0.0412(2) 0.0023(2) -0.0017(2) -0.00545(18) C2 0.035(3) 0.043(3) 0.039(4) 0.003(3) -0.002(3) 0.010(2) C3 0.038(3) 0.052(3) 0.049(4) 0.002(4) -0.003(3) -0.004(3) N1 0.038(3) 0.042(3) 0.041(3) -0.002(3) 0.000(2) 0.001(2) C4 0.054(5) 0.051(4) 0.052(4) -0.001(3) -0.014(4) -0.005(3) C5 0.055(4) 0.061(4) 0.041(3) -0.009(4) -0.009(3) 0.009(4) C6 0.050(4) 0.056(4) 0.039(4) -0.003(3) 0.008(3) 0.003(3) 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' 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 N1 C2 C3 119.4(6) . . ? N1 C2 I1 117.8(5) . . ? C3 C2 I1 122.8(5) . . ? C2 C3 C4 118.8(7) . . ? C2 N1 C6 121.8(6) . . ? C5 C4 C3 119.8(7) . . ? C6 C5 C4 119.1(7) . . ? C5 C6 N1 121.0(7) . . ? 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 2.096(6) . ? C2 N1 1.342(9) . ? C2 C3 1.364(9) . ? C3 C4 1.400(12) . ? N1 C6 1.343(9) . ? C4 C5 1.374(12) . ? C5 C6 1.336(11) . ?