#------------------------------------------------------------------------------ #$Date: 2020-05-13 04:35:15 +0300 (Wed, 13 May 2020) $ #$Revision: 252006 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/05/7240502.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_7240502 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, Br' _chemical_formula_sum 'C5 H5 Br I N' _chemical_formula_weight 285.91 _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 91.693(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 4.5838(2) _cell_length_b 14.8642(5) _cell_length_c 10.6931(3) _cell_measurement_reflns_used 3351 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 36.5721 _cell_measurement_theta_min 3.8139 _cell_volume 728.25(5) _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 ; Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790 ; _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 16.3426 _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.991 _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 0.0490 _diffrn_reflns_av_unetI/netI 0.0372 _diffrn_reflns_Laue_measured_fraction_full 0.992 _diffrn_reflns_Laue_measured_fraction_max 0.991 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 8044 _diffrn_reflns_point_group_measured_fraction_full 0.992 _diffrn_reflns_point_group_measured_fraction_max 0.991 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.981 _diffrn_reflns_theta_min 4.052 _diffrn_source 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 9.782 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.30647 _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 2.608 _exptl_crystal_description needle _exptl_crystal_F_000 520 _exptl_crystal_size_max 0.62 _exptl_crystal_size_mid 0.41 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.838 _refine_diff_density_min -1.093 _refine_diff_density_rms 0.123 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.900 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 73 _refine_ls_number_reflns 1565 _refine_ls_number_restraints 31 _refine_ls_restrained_S_all 0.892 _refine_ls_R_factor_all 0.0442 _refine_ls_R_factor_gt 0.0290 _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^)+(0.0362P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0625 _refine_ls_wR_factor_ref 0.0651 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1151 _reflns_number_total 1565 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ce00534g2.cif _cod_data_source_block 3-IPyHBr _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7240502 _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 PRELIM in P2(1)/c shelx.res created by SHELXL-2018/3 at 10:45:10 on 15-Oct-2019 CELL 0.71073 4.5838 14.8642 10.6931 90.000 91.693 90.000 ZERR 4.00 0.0002 0.0005 0.0003 0.000 0.003 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H N BR I UNIT 20 20 4 4 4 MERG 2 OMIT -4.00 54.00 OMIT 0 0 2 OMIT 0 4 0 DELU 0.010 0.010 C5 C4 C2 C6 c3 SIMU 0.040 0.080 1.700 C5 C4 C2 C6 c3 FMAP 2 PLAN 25 ACTA L.S. 50 WGHT 0.036200 FVAR 3.75219 I1 5 0.731556 0.372110 -0.073118 11.00000 0.05496 0.04669 = 0.03879 -0.00303 0.00401 -0.00319 BR1 4 0.924928 0.109984 0.126022 11.00000 0.05418 0.04983 = 0.03889 0.00216 0.00323 0.00126 N1 3 0.642318 0.438860 0.312437 11.00000 0.05651 0.05366 = 0.04011 -0.01066 -0.00132 0.00129 AFIX 43 H1 2 0.722126 0.478022 0.361775 11.00000 -1.20000 AFIX 0 C5 1 0.321626 0.318502 0.281544 11.00000 0.04314 0.04809 = 0.05719 0.01220 0.00812 -0.00069 AFIX 43 H5 2 0.182211 0.279423 0.312098 11.00000 -1.20000 AFIX 0 C3 1 0.604878 0.372961 0.113362 11.00000 0.04239 0.03277 = 0.03566 0.00385 -0.00066 0.00334 C4 1 0.405103 0.311773 0.159388 11.00000 0.04964 0.03987 = 0.04665 0.00077 -0.00306 -0.00011 AFIX 43 H4 2 0.328502 0.266627 0.107934 11.00000 -1.20000 AFIX 0 C2 1 0.720847 0.436393 0.193666 11.00000 0.04728 0.04216 = 0.04364 0.00120 0.00439 0.00060 AFIX 43 H2 2 0.855097 0.477902 0.164942 11.00000 -1.20000 AFIX 0 C6 1 0.444027 0.382711 0.357783 11.00000 0.05939 0.06282 = 0.03915 0.00678 0.00715 0.00931 AFIX 43 H6 2 0.389770 0.387324 0.440657 11.00000 -1.20000 AFIX 0 HKLF 4 REM PRELIM in P2(1)/c REM wR2 = 0.0651, GooF = S = 0.900, Restrained GooF = 0.892 for all data REM R1 = 0.0290 for 1151 Fo > 4sig(Fo) and 0.0442 for all 1565 data REM 73 parameters refined using 31 restraints END WGHT 0.0358 0.0000 REM Highest difference peak 0.838, deepest hole -1.093, 1-sigma level 0.123 Q1 1 0.7321 0.4301 -0.0704 11.00000 0.05 0.84 Q2 1 0.5977 0.3717 0.0001 11.00000 0.05 0.61 Q3 1 0.7384 0.3116 -0.0641 11.00000 0.05 0.52 Q4 1 0.7564 0.1116 0.2007 11.00000 0.05 0.41 Q5 1 0.4112 0.3719 -0.1731 11.00000 0.05 0.40 Q6 1 0.6255 0.3914 0.5109 11.00000 0.05 0.38 Q7 1 0.6866 0.2057 0.2454 11.00000 0.05 0.37 Q8 1 0.8382 0.1191 0.2134 11.00000 0.05 0.36 Q9 1 0.6587 0.5611 0.2156 11.00000 0.05 0.35 Q10 1 0.8243 0.3742 -0.1512 11.00000 0.05 0.35 Q11 1 0.9342 0.1681 0.1326 11.00000 0.05 0.34 Q12 1 0.1669 0.3895 0.1162 11.00000 0.05 0.34 Q13 1 0.0937 0.3806 0.4652 11.00000 0.05 0.34 Q14 1 0.3012 0.4498 0.0162 11.00000 0.05 0.34 Q15 1 0.8459 0.5751 0.0186 11.00000 0.05 0.33 Q16 1 0.7339 0.0506 0.2531 11.00000 0.05 0.33 Q17 1 1.0960 0.3674 -0.1350 11.00000 0.05 0.32 Q18 1 0.3000 0.3773 0.5845 11.00000 0.05 0.32 Q19 1 0.7895 0.2464 -0.1040 11.00000 0.05 0.31 Q20 1 0.3202 0.3796 0.3112 11.00000 0.05 0.31 Q21 1 0.8463 0.5477 0.1613 11.00000 0.05 0.30 Q22 1 0.8307 0.3726 0.2180 11.00000 0.05 0.30 Q23 1 0.9264 0.0520 0.1345 11.00000 0.05 0.30 Q24 1 0.5852 0.3394 0.1243 11.00000 0.05 0.30 Q25 1 1.1943 0.1129 0.1835 11.00000 0.05 0.30 ; _shelx_res_checksum 13737 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 I1 I 0.73156(7) 0.37211(2) -0.07312(3) 0.04676(13) Uani 1 1 d . . . . . Br1 Br 0.92493(11) 0.10998(3) 0.12602(4) 0.04760(15) Uani 1 1 d . . . . . N1 N 0.6423(8) 0.4389(3) 0.3124(3) 0.0501(10) Uani 1 1 d . . . . . H1 H 0.722126 0.478022 0.361775 0.060 Uiso 1 1 calc R U . . . C5 C 0.3216(9) 0.3185(4) 0.2815(4) 0.0493(12) Uani 1 1 d . U . . . H5 H 0.182211 0.279423 0.312098 0.059 Uiso 1 1 calc R U . . . C3 C 0.6049(9) 0.3730(3) 0.1134(4) 0.0370(10) Uani 1 1 d . U . . . C4 C 0.4051(10) 0.3118(3) 0.1594(4) 0.0455(11) Uani 1 1 d . U . . . H4 H 0.328502 0.266627 0.107934 0.055 Uiso 1 1 calc R U . . . C2 C 0.7208(9) 0.4364(3) 0.1937(4) 0.0443(11) Uani 1 1 d . U . . . H2 H 0.855097 0.477902 0.164942 0.053 Uiso 1 1 calc R U . . . C6 C 0.4440(11) 0.3827(4) 0.3578(5) 0.0537(13) Uani 1 1 d . U . . . H6 H 0.389770 0.387324 0.440657 0.064 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 0.0550(2) 0.0467(2) 0.03879(17) -0.00303(14) 0.00401(13) -0.00319(14) Br1 0.0542(3) 0.0498(3) 0.0389(2) 0.0022(2) 0.0032(2) 0.0013(2) N1 0.057(3) 0.054(3) 0.040(2) -0.011(2) -0.0013(19) 0.001(2) C5 0.043(3) 0.048(3) 0.057(3) 0.012(2) 0.008(2) -0.001(2) C3 0.042(3) 0.033(2) 0.036(2) 0.0039(18) -0.0007(18) 0.0033(18) C4 0.050(3) 0.040(3) 0.047(2) 0.001(2) -0.003(2) 0.000(2) C2 0.047(3) 0.042(3) 0.044(2) 0.001(2) 0.004(2) 0.001(2) C6 0.059(3) 0.063(4) 0.039(2) 0.007(2) 0.007(2) 0.009(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' Br Br -0.2901 2.4595 '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 C2 N1 C6 122.4(4) . . ? C6 C5 C4 119.8(4) . . ? C2 C3 C4 118.4(4) . . ? C2 C3 I1 119.2(3) . . ? C4 C3 I1 122.5(3) . . ? C5 C4 C3 119.5(4) . . ? N1 C2 C3 120.4(4) . . ? N1 C6 C5 119.5(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 C3 2.093(4) . ? N1 C2 1.331(5) . ? N1 C6 1.336(6) . ? C5 C6 1.365(7) . ? C5 C4 1.376(6) . ? C3 C2 1.372(6) . ? C3 C4 1.391(6) . ?