#------------------------------------------------------------------------------ #$Date: 2020-05-13 04:35:15 +0300 (Wed, 13 May 2020) $ #$Revision: 252006 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/05/7240503.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_7240503 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, I' _chemical_formula_sum 'C5 H5 I2 N' _chemical_formula_weight 332.90 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 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 101.885(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 4.57920(10) _cell_length_b 21.7962(6) _cell_length_c 8.1293(3) _cell_measurement_reflns_used 5056 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 36.2588 _cell_measurement_theta_min 3.7306 _cell_volume 793.99(4) _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 0.994 _diffrn_measured_fraction_theta_max 0.994 _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 0.0471 _diffrn_reflns_av_unetI/netI 0.0343 _diffrn_reflns_Laue_measured_fraction_full 0.994 _diffrn_reflns_Laue_measured_fraction_max 0.994 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 12719 _diffrn_reflns_point_group_measured_fraction_full 0.994 _diffrn_reflns_point_group_measured_fraction_max 0.994 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.957 _diffrn_reflns_theta_min 3.739 _diffrn_source 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 7.829 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.40369 _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 2.785 _exptl_crystal_description block _exptl_crystal_F_000 592 _exptl_crystal_size_max 0.66 _exptl_crystal_size_mid 0.51 _exptl_crystal_size_min 0.36 _refine_diff_density_max 0.808 _refine_diff_density_min -0.610 _refine_diff_density_rms 0.130 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.903 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 61 _refine_ls_number_reflns 1717 _refine_ls_number_restraints 31 _refine_ls_restrained_S_all 0.896 _refine_ls_R_factor_all 0.0450 _refine_ls_R_factor_gt 0.0281 _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^)+(0.0342P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0593 _refine_ls_wR_factor_ref 0.0618 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1241 _reflns_number_total 1717 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ce00534g2.cif _cod_data_source_block 4-IPyHI _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7240503 _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 1 21/c 1 shelx.res created by SHELXL-2018/3 at 11:56:09 on 15-Oct-2019 CELL 0.71073 4.5792 21.7962 8.1293 90.000 101.885 90.000 ZERR 4.00 0.0001 0.0006 0.0003 0.000 0.003 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H N I UNIT 20 20 4 8 MERG 2 OMIT -4.00 54.00 OMIT 1 2 0 OMIT 1 1 0 OMIT 1 0 0 OMIT 0 4 1 OMIT -1 7 3 DELU 0.010 0.010 N1 C3 C2 C6 C5 SIMU 0.040 0.080 1.700 N1 C3 C2 C6 C5 EADP C2 C6 EADP C3 C5 FMAP 2 PLAN 25 ACTA BOND $H CONF L.S. 40 TEMP 25.00 WGHT 0.034200 FVAR 2.55040 I2 4 -0.448027 0.182894 1.230613 11.00000 0.04865 0.03918 = 0.05995 0.00257 0.01590 0.00015 I1 4 0.294514 -0.023950 0.743957 11.00000 0.06023 0.03947 = 0.05373 -0.00027 0.01294 0.00452 N1 3 0.010504 0.188479 0.723610 11.00000 0.05933 0.03820 = 0.05598 -0.00537 0.00053 0.00486 AFIX 43 H1 2 -0.046657 0.226140 0.718482 11.00000 -1.20000 AFIX 0 C3 1 0.242182 0.107565 0.613906 11.00000 0.05692 0.04925 = 0.04941 -0.00063 0.02022 0.00075 AFIX 43 H3 2 0.342877 0.092204 0.534426 11.00000 -1.20000 AFIX 0 C2 1 0.159004 0.167576 0.608595 11.00000 0.05509 0.04784 = 0.04834 -0.00516 0.01327 -0.00389 AFIX 43 H2 2 0.204120 0.193674 0.526806 11.00000 -1.20000 AFIX 0 C6 1 -0.051603 0.152714 0.845954 11.00000 0.05509 0.04784 = 0.04834 -0.00516 0.01327 -0.00389 AFIX 43 H6 2 -0.147247 0.169225 0.926228 11.00000 -1.20000 AFIX 0 C5 1 0.024825 0.092301 0.853134 11.00000 0.05692 0.04925 = 0.04941 -0.00063 0.02022 0.00075 AFIX 43 H5 2 -0.024767 0.066778 0.934888 11.00000 -1.20000 AFIX 0 C4 1 0.177649 0.069723 0.736352 11.00000 0.04435 0.03639 = 0.03758 -0.00202 0.00446 -0.00192 HKLF 4 REM SIR92 run in space group P 1 21/c 1 REM wR2 = 0.0618, GooF = S = 0.903, Restrained GooF = 0.896 for all data REM R1 = 0.0281 for 1241 Fo > 4sig(Fo) and 0.0450 for all 1717 data REM 61 parameters refined using 31 restraints END WGHT 0.0347 0.0000 REM Highest difference peak 0.808, deepest hole -0.610, 1-sigma level 0.130 Q1 1 0.2677 0.0210 0.7578 11.00000 0.05 0.81 Q2 1 -0.4527 0.1383 1.2148 11.00000 0.05 0.77 Q3 1 0.3260 -0.0635 0.7673 11.00000 0.05 0.72 Q4 1 -0.4369 0.2268 1.2198 11.00000 0.05 0.67 Q5 1 0.3069 -0.0037 0.6529 11.00000 0.05 0.57 Q6 1 -0.1879 -0.0218 0.7316 11.00000 0.05 0.54 Q7 1 -0.7013 0.1111 1.2493 11.00000 0.05 0.53 Q8 1 -0.2940 0.1597 0.7422 11.00000 0.05 0.52 Q9 1 0.2663 -0.0330 0.8839 11.00000 0.05 0.47 Q10 1 -0.5523 0.2672 1.2660 11.00000 0.05 0.47 Q11 1 0.4598 0.1335 0.7618 11.00000 0.05 0.47 Q12 1 -0.4465 0.2101 1.3239 11.00000 0.05 0.45 Q13 1 0.0420 0.3151 0.7497 11.00000 0.05 0.44 Q14 1 0.1957 -0.0232 0.8334 11.00000 0.05 0.44 Q15 1 -0.0914 0.1804 1.2550 11.00000 0.05 0.44 Q16 1 0.2632 -0.0516 0.6399 11.00000 0.05 0.43 Q17 1 -0.1006 0.1124 0.8269 11.00000 0.05 0.40 Q18 1 0.0892 0.2271 0.7269 11.00000 0.05 0.40 Q19 1 0.0979 0.1284 0.9036 11.00000 0.05 0.38 Q20 1 -0.4985 0.1830 1.3396 11.00000 0.05 0.37 Q21 1 -0.0037 0.1777 0.8252 11.00000 0.05 0.36 Q22 1 0.1324 0.1790 0.6706 11.00000 0.05 0.36 Q23 1 -0.3721 0.1757 1.1407 11.00000 0.05 0.35 Q24 1 0.6130 -0.0285 0.7579 11.00000 0.05 0.34 Q25 1 -0.0587 0.1310 0.7564 11.00000 0.05 0.34 ; _shelx_res_checksum 29730 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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 I2 I -0.44803(8) 0.18289(2) 1.23061(5) 0.04858(13) Uani 1 1 d . . . . . I1 I 0.29451(9) -0.02395(2) 0.74396(5) 0.05097(13) Uani 1 1 d . . . . . N1 N 0.0105(10) 0.1885(2) 0.7236(6) 0.0528(12) Uani 1 1 d . U . . . H1 H -0.046657 0.226140 0.718482 0.063 Uiso 1 1 calc R U . . . C3 C 0.2422(12) 0.1076(2) 0.6139(7) 0.0505(10) Uani 1 1 d . U . . . H3 H 0.342877 0.092204 0.534426 0.061 Uiso 1 1 calc R U . . . C2 C 0.1590(13) 0.1676(2) 0.6086(7) 0.0500(9) Uani 1 1 d . U . . . H2 H 0.204120 0.193674 0.526806 0.060 Uiso 1 1 calc R U . . . C6 C -0.0516(12) 0.1527(2) 0.8460(8) 0.0500(9) Uani 1 1 d . U . . . H6 H -0.147247 0.169225 0.926228 0.060 Uiso 1 1 calc R U . . . C5 C 0.0248(12) 0.0923(2) 0.8531(7) 0.0505(10) Uani 1 1 d . U . . . H5 H -0.024767 0.066778 0.934888 0.061 Uiso 1 1 calc R U . . . C4 C 0.1776(11) 0.0697(2) 0.7364(6) 0.0400(12) 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 I2 0.0486(2) 0.0392(2) 0.0600(3) 0.00257(18) 0.01590(18) 0.00015(15) I1 0.0602(2) 0.0395(2) 0.0537(3) -0.00027(17) 0.01294(18) 0.00452(16) N1 0.059(3) 0.038(2) 0.056(3) -0.005(2) 0.001(2) 0.005(2) C3 0.057(2) 0.049(2) 0.049(3) -0.0006(19) 0.020(2) 0.0007(18) C2 0.055(2) 0.048(2) 0.048(3) -0.0052(18) 0.0133(19) -0.0039(18) C6 0.055(2) 0.048(2) 0.048(3) -0.0052(18) 0.0133(19) -0.0039(18) C5 0.057(2) 0.049(2) 0.049(3) -0.0006(19) 0.020(2) 0.0007(18) C4 0.044(3) 0.036(3) 0.038(3) -0.002(2) 0.004(2) -0.002(2) 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 C6 N1 C2 122.3(5) . . ? C6 N1 H1 118.8 . . ? C2 N1 H1 118.8 . . ? C2 C3 C4 120.0(5) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? N1 C2 C3 118.8(5) . . ? N1 C2 H2 120.6 . . ? C3 C2 H2 120.6 . . ? N1 C6 C5 120.2(5) . . ? N1 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C6 C5 C4 118.5(5) . . ? C6 C5 H5 120.7 . . ? C4 C5 H5 120.7 . . ? C3 C4 C5 120.0(5) . . ? C3 C4 I1 120.8(4) . . ? C5 C4 I1 119.1(4) . . ? 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 2.108(5) . ? N1 C6 1.339(7) . ? N1 C2 1.344(7) . ? N1 H1 0.8600 . ? C3 C2 1.361(7) . ? C3 C4 1.371(7) . ? C3 H3 0.9300 . ? C2 H2 0.9300 . ? C6 C5 1.361(7) . ? C6 H6 0.9300 . ? C5 C4 1.381(7) . ? 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 1.8(8) . . . . ? C4 C3 C2 N1 -0.8(8) . . . . ? C2 N1 C6 C5 -2.8(9) . . . . ? N1 C6 C5 C4 2.7(8) . . . . ? C2 C3 C4 C5 0.8(8) . . . . ? C2 C3 C4 I1 178.5(4) . . . . ? C6 C5 C4 C3 -1.7(8) . . . . ? C6 C5 C4 I1 -179.4(4) . . . . ?