#------------------------------------------------------------------------------ #$Date: 2024-11-09 14:07:10 +0200 (Sat, 09 Nov 2024) $ #$Revision: 295862 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/05/7240501.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_7240501 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, 0.5(H2 O)' _chemical_formula_sum 'C5 H6 Cl I N O0.5' _chemical_formula_weight 250.46 _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 mixed _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 90.722(10) _cell_angle_beta 99.454(10) _cell_angle_gamma 119.570(13) _cell_formula_units_Z 4 _cell_length_a 8.0102(9) _cell_length_b 8.0918(10) _cell_length_c 14.0480(18) _cell_measurement_reflns_used 2711 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 36.6148 _cell_measurement_theta_min 3.9134 _cell_volume 776.5(2) _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 0.970 _diffrn_measured_fraction_theta_max 0.957 _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 0.0444 _diffrn_reflns_av_unetI/netI 0.0532 _diffrn_reflns_Laue_measured_fraction_full 0.970 _diffrn_reflns_Laue_measured_fraction_max 0.957 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 5112 _diffrn_reflns_point_group_measured_fraction_full 0.970 _diffrn_reflns_point_group_measured_fraction_max 0.957 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.999 _diffrn_reflns_theta_min 3.919 _diffrn_source 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 4.381 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.39500 _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 2.142 _exptl_crystal_description needle _exptl_crystal_F_000 468 _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _refine_diff_density_max 0.817 _refine_diff_density_min -0.840 _refine_diff_density_rms 0.107 _refine_ls_extinction_coef 0.0100(7) _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 0.910 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 163 _refine_ls_number_reflns 3240 _refine_ls_number_restraints 3 _refine_ls_restrained_S_all 0.910 _refine_ls_R_factor_all 0.0426 _refine_ls_R_factor_gt 0.0297 _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^)+(0.0317P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0655 _refine_ls_wR_factor_ref 0.0678 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2434 _reflns_number_total 3240 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ce00534g2.cif _cod_data_source_block (3-IPyHCl)2H2O _cod_depositor_comments ; 2024-11-08 Z value and formula fixed to values more according to usual chemical conventions. miguel ; _cod_original_formula_sum 'C10 H12 Cl2 I2 N2 O' _cod_original_formula_weight 500.92 _cod_original_formula_moiety '2(C5 H5 I N), 2(Cl), H2 O' _cod_original_formula_units_Z 2 _cod_original_cell_volume 776.53(19) _cod_database_code 7240501 _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 OPTI_TRIKLINSKI in P-1 shelx.res created by SHELXL-2018/3 at 14:10:18 on 15-Oct-2019 CELL 0.71073 8.0102 8.0918 14.0480 90.722 99.454 119.570 ZERR 2.00 0.0009 0.0010 0.0018 0.010 0.010 0.013 LATT 1 SFAC C H N CL I O UNIT 20 24 4 4 4 2 MERG 2 OMIT -4.00 54.00 OMIT -1 1 3 OMIT 0 2 0 OMIT -1 -1 3 OMIT 1 -1 2 DFIX 0.96 0.04 O1 H7 O1 H8 dang 1.5 0.08 H7 H8 DELU 0.010 0.010 CL1 CL2 O1 SIMU 0.040 0.080 1.700 CL1 CL2 O1 FMAP 2 PLAN 20 ACTA L.S. 50 WGHT 0.031700 EXTI 0.010046 FVAR 4.61435 I2 5 0.236616 0.793510 0.658690 11.00000 0.03494 0.04523 = 0.04462 0.00392 0.00499 0.02032 I1 5 0.950516 0.762359 0.900901 11.00000 0.04163 0.05061 = 0.04760 0.00607 0.00611 0.02267 CL1 4 0.228964 0.727407 0.352278 11.00000 0.04611 0.05370 = 0.05279 0.00583 0.00667 0.02526 CL2 4 0.575033 0.733583 0.772130 11.00000 0.04003 0.09082 = 0.05457 0.01558 0.00976 0.03597 O1 6 0.180900 0.337563 0.776336 11.00000 0.05209 0.06327 = 0.08883 0.01734 0.00232 0.02801 N1A 3 -0.227955 0.912169 0.580503 11.00000 0.04943 0.05337 = 0.05699 0.01244 0.01916 0.03418 AFIX 43 H1A 2 -0.257677 0.990753 0.603967 11.00000 -1.20000 AFIX 0 N1 3 1.338317 0.778311 1.152710 11.00000 0.05660 0.05738 = 0.03609 0.00087 0.00394 0.02998 AFIX 43 H1 2 1.341424 0.788292 1.214079 11.00000 -1.20000 AFIX 0 C5 1 1.477808 0.745977 1.025800 11.00000 0.04110 0.05247 = 0.07224 0.00602 0.01850 0.02328 AFIX 43 H5 2 1.575673 0.735258 1.003693 11.00000 -1.20000 AFIX 0 C5A 1 -0.300656 0.672131 0.462203 11.00000 0.03410 0.04716 = 0.04882 0.00634 0.00284 0.00947 AFIX 43 H5A 2 -0.380497 0.589813 0.406614 11.00000 -1.20000 AFIX 0 C2A 1 -0.066131 0.915221 0.625965 11.00000 0.04106 0.04511 = 0.04020 0.00356 0.00736 0.02193 AFIX 43 H2A 2 0.010697 0.999452 0.681398 11.00000 -1.20000 AFIX 0 C4 1 1.329070 0.747013 0.961056 11.00000 0.04341 0.05145 = 0.04877 0.00740 0.01868 0.01943 AFIX 43 H4 2 1.325884 0.735906 0.894723 11.00000 -1.20000 AFIX 0 C6A 1 -0.345443 0.796256 0.501794 11.00000 0.03707 0.06150 = 0.05308 0.02447 0.01411 0.02459 AFIX 43 H6A 2 -0.457257 0.799479 0.473833 11.00000 -1.20000 AFIX 0 C2 1 1.194154 0.780934 1.092533 11.00000 0.04937 0.04930 = 0.04907 0.00297 0.01302 0.02798 AFIX 43 H2 2 1.099695 0.793925 1.117014 11.00000 -1.20000 AFIX 0 C6 1 1.479181 0.760891 1.122595 11.00000 0.04443 0.05351 = 0.06496 0.00289 -0.00518 0.02832 AFIX 43 H6 2 1.577398 0.758966 1.167391 11.00000 -1.20000 AFIX 0 C3A 1 -0.015474 0.792286 0.589536 11.00000 0.02702 0.03869 = 0.03993 0.00905 0.00934 0.01492 C3 1 1.183825 0.764564 0.994350 11.00000 0.03882 0.03220 = 0.04442 0.00128 0.00536 0.01183 C4A 1 -0.133639 0.671321 0.506588 11.00000 0.04110 0.03974 = 0.05669 0.00598 0.00624 0.02026 AFIX 43 H4A 2 -0.100455 0.588080 0.480171 11.00000 -1.20000 AFIX 0 H7 2 0.290286 0.442842 0.767630 11.00000 0.09712 H8 2 0.093672 0.355315 0.727227 11.00000 0.15286 HKLF 4 REM OPTI_TRIKLINSKI in P-1 REM wR2 = 0.0678, GooF = S = 0.910, Restrained GooF = 0.910 for all data REM R1 = 0.0297 for 2434 Fo > 4sig(Fo) and 0.0426 for all 3240 data REM 163 parameters refined using 3 restraints END WGHT 0.0317 0.0000 REM Highest difference peak 0.817, deepest hole -0.840, 1-sigma level 0.107 Q1 1 0.9974 0.6978 0.8820 11.00000 0.05 0.82 Q2 1 0.2955 0.7181 0.6463 11.00000 0.05 0.60 Q3 1 0.2084 0.8615 0.6813 11.00000 0.05 0.56 Q4 1 0.2935 0.7496 0.7203 11.00000 0.05 0.54 Q5 1 0.1759 0.8309 0.5893 11.00000 0.05 0.53 Q6 1 -0.4664 0.8286 0.4208 11.00000 0.05 0.51 Q7 1 0.2462 0.7560 0.5743 11.00000 0.05 0.50 Q8 1 0.8590 0.8363 0.8987 11.00000 0.05 0.49 Q9 1 0.9783 0.7438 0.8142 11.00000 0.05 0.46 Q10 1 0.2411 0.8530 0.7529 11.00000 0.05 0.44 Q11 1 0.8807 0.7898 0.8340 11.00000 0.05 0.44 Q12 1 1.0160 0.7210 0.9620 11.00000 0.05 0.43 Q13 1 1.6556 0.7275 1.1495 11.00000 0.05 0.39 Q14 1 -0.1856 0.3774 0.4563 11.00000 0.05 0.38 Q15 1 0.9418 0.7793 0.9745 11.00000 0.05 0.37 Q16 1 0.4734 0.8815 0.7492 11.00000 0.05 0.34 Q17 1 0.5850 0.6412 0.7706 11.00000 0.05 0.34 Q18 1 -0.1835 0.7217 0.4832 11.00000 0.05 0.33 Q19 1 1.0263 0.8997 0.8568 11.00000 0.05 0.31 Q20 1 0.7386 0.5786 0.8889 11.00000 0.05 0.31 ; _shelx_res_checksum 79194 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 I2 I 0.23662(4) 0.79351(4) 0.65869(2) 0.04190(12) Uani 1 1 d . . . . . I1 I 0.95052(5) 0.76236(4) 0.90090(2) 0.04717(12) Uani 1 1 d . . . . . Cl1 Cl 0.22896(19) 0.72741(17) 0.35228(8) 0.0512(3) Uani 1 1 d . . . . . Cl2 Cl 0.57503(18) 0.7336(2) 0.77213(8) 0.0603(4) Uani 1 1 d . . . . . O1 O 0.1809(7) 0.3376(6) 0.7763(3) 0.0699(10) Uani 1 1 d D . . . . N1A N -0.2280(6) 0.9122(5) 0.5805(3) 0.0483(9) Uani 1 1 d . . . . . H1A H -0.257677 0.990753 0.603967 0.058 Uiso 1 1 calc R U . . . N1 N 1.3383(6) 0.7783(5) 1.1527(2) 0.0501(10) Uani 1 1 d . . . . . H1 H 1.341424 0.788292 1.214079 0.060 Uiso 1 1 calc R U . . . C5 C 1.4778(7) 0.7460(7) 1.0258(3) 0.0544(12) Uani 1 1 d . . . . . H5 H 1.575673 0.735258 1.003693 0.065 Uiso 1 1 calc R U . . . C5A C -0.3007(7) 0.6721(6) 0.4622(3) 0.0489(11) Uani 1 1 d . . . . . H5A H -0.380497 0.589813 0.406614 0.059 Uiso 1 1 calc R U . . . C2A C -0.0661(7) 0.9152(6) 0.6260(3) 0.0421(10) Uani 1 1 d . . . . . H2A H 0.010697 0.999452 0.681398 0.051 Uiso 1 1 calc R U . . . C4 C 1.3291(7) 0.7470(6) 0.9611(3) 0.0486(11) Uani 1 1 d . . . . . H4 H 1.325884 0.735906 0.894723 0.058 Uiso 1 1 calc R U . . . C6A C -0.3454(7) 0.7963(7) 0.5018(3) 0.0498(12) Uani 1 1 d . . . . . H6A H -0.457257 0.799479 0.473833 0.060 Uiso 1 1 calc R U . . . C2 C 1.1942(7) 0.7809(6) 1.0925(3) 0.0474(11) Uani 1 1 d . . . . . H2 H 1.099695 0.793925 1.117014 0.057 Uiso 1 1 calc R U . . . C6 C 1.4792(8) 0.7609(7) 1.1226(4) 0.0548(13) Uani 1 1 d . . . . . H6 H 1.577398 0.758966 1.167391 0.066 Uiso 1 1 calc R U . . . C3A C -0.0155(6) 0.7923(6) 0.5895(3) 0.0355(9) Uani 1 1 d . . . . . C3 C 1.1838(7) 0.7646(6) 0.9944(3) 0.0416(10) Uani 1 1 d . . . . . C4A C -0.1336(7) 0.6713(6) 0.5066(3) 0.0463(11) Uani 1 1 d . . . . . H4A H -0.100455 0.588080 0.480171 0.056 Uiso 1 1 calc R U . . . H7 H 0.290(6) 0.443(6) 0.768(4) 0.10(2) Uiso 1 1 d D . . . . H8 H 0.094(9) 0.355(10) 0.727(4) 0.15(3) Uiso 1 1 d 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 0.03494(19) 0.04523(19) 0.04462(18) 0.00392(12) 0.00499(12) 0.02032(16) I1 0.0416(2) 0.0506(2) 0.04760(19) 0.00607(13) 0.00611(14) 0.02267(17) Cl1 0.0461(7) 0.0537(7) 0.0528(6) 0.0058(5) 0.0067(5) 0.0253(6) Cl2 0.0400(8) 0.0908(10) 0.0546(7) 0.0156(6) 0.0098(6) 0.0360(8) O1 0.052(3) 0.063(3) 0.089(3) 0.017(2) 0.002(2) 0.028(2) N1A 0.049(3) 0.053(2) 0.057(2) 0.0124(18) 0.019(2) 0.034(2) N1 0.057(3) 0.057(2) 0.0361(18) 0.0009(16) 0.0039(18) 0.030(2) C5 0.041(3) 0.052(3) 0.072(3) 0.006(2) 0.018(2) 0.023(3) C5A 0.034(3) 0.047(3) 0.049(2) 0.006(2) 0.003(2) 0.009(2) C2A 0.041(3) 0.045(3) 0.040(2) 0.0036(18) 0.0074(19) 0.022(2) C4 0.043(3) 0.051(3) 0.049(2) 0.007(2) 0.019(2) 0.019(3) C6A 0.037(3) 0.061(3) 0.053(3) 0.024(2) 0.014(2) 0.025(3) C2 0.049(3) 0.049(3) 0.049(2) 0.003(2) 0.013(2) 0.028(3) C6 0.044(3) 0.054(3) 0.065(3) 0.003(2) -0.005(2) 0.028(3) C3A 0.027(2) 0.039(2) 0.040(2) 0.0090(17) 0.0093(18) 0.015(2) C3 0.039(3) 0.032(2) 0.044(2) 0.0013(18) 0.005(2) 0.012(2) C4A 0.041(3) 0.040(2) 0.057(3) 0.006(2) 0.006(2) 0.020(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' 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' O O 0.0106 0.0060 '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 C6A N1A C2A 124.3(4) . . ? C2 N1 C6 123.1(4) . . ? C6 C5 C4 119.0(4) . . ? C6A C5A C4A 118.5(4) . . ? N1A C2A C3A 118.8(4) . . ? C5 C4 C3 120.4(4) . . ? N1A C6A C5A 119.2(4) . . ? N1 C2 C3 120.1(4) . . ? N1 C6 C5 119.5(4) . . ? C2A C3A C4A 118.3(4) . . ? C2A C3A I2 119.8(3) . . ? C4A C3A I2 121.9(3) . . ? C2 C3 C4 117.9(4) . . ? C2 C3 I1 119.3(4) . . ? C4 C3 I1 122.8(3) . . ? C3A C4A C5A 121.0(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 I2 C3A 2.087(4) . ? I1 C3 2.092(5) . ? N1A C6A 1.322(5) . ? N1A C2A 1.336(5) . ? N1 C2 1.324(5) . ? N1 C6 1.336(6) . ? C5 C6 1.361(6) . ? C5 C4 1.379(6) . ? C5A C6A 1.362(6) . ? C5A C4A 1.383(6) . ? C2A C3A 1.367(5) . ? C4 C3 1.390(6) . ? C2 C3 1.369(6) . ? C3A C4A 1.381(6) . ?