#------------------------------------------------------------------------------ #$Date: 2020-05-13 04:35:15 +0300 (Wed, 13 May 2020) $ #$Revision: 252006 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/05/7240505.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_7240505 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 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 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 _cell_angle_beta 91.478(7) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 4.6289(2) _cell_length_b 15.1319(8) _cell_length_c 11.0844(9) _cell_measurement_reflns_used 4568 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 37.3831 _cell_measurement_theta_min 4.0291 _cell_volume 776.14(8) _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 ; Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8. ; _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 0.996 _diffrn_measured_fraction_theta_max 0.996 _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 0.0718 _diffrn_reflns_av_unetI/netI 0.0529 _diffrn_reflns_Laue_measured_fraction_full 0.996 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_number 4872 _diffrn_reflns_point_group_measured_fraction_full 0.996 _diffrn_reflns_point_group_measured_fraction_max 0.996 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.997 _diffrn_reflns_theta_min 4.404 _diffrn_source 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 8.009 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.36106 _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 2.849 _exptl_crystal_description block _exptl_crystal_F_000 592 _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.27 _refine_diff_density_max 1.228 _refine_diff_density_min -1.566 _refine_diff_density_rms 0.198 _refine_ls_extinction_coef 0.0061(5) _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 0.924 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 78 _refine_ls_number_reflns 1683 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.924 _refine_ls_R_factor_all 0.0347 _refine_ls_R_factor_gt 0.0310 _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^)+(0.0558P)^2^+0.2022P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0782 _refine_ls_wR_factor_ref 0.0803 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1524 _reflns_number_total 1683 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ce00534g2.cif _cod_data_source_block 3-IPyHI _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7240505 _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 2 in P2(1)/c shelx.res created by SHELXL-2018/3 at 14:16:31 on 27-Jun-2019 CELL 0.71073 4.6289 15.1319 11.0844 90.000 91.478 90.000 ZERR 4.00 0.0002 0.0008 0.0009 0.000 0.007 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 FMAP 2 PLAN 20 ACTA L.S. 10 WGHT 0.055800 0.202200 EXTI 0.006127 FVAR 3.46504 I1 4 0.402031 0.388738 0.126147 11.00000 0.02636 0.01857 = 0.01637 -0.00054 0.00369 0.00000 I2 4 0.223386 0.374609 0.431959 11.00000 0.03181 0.02054 = 0.01621 -0.00111 0.00504 -0.00269 C4 1 -0.100490 0.312106 0.654055 11.00000 0.02682 0.01780 = 0.02171 -0.00210 -0.00031 0.00024 AFIX 43 H4 2 -0.178364 0.269470 0.602276 11.00000 -1.20000 AFIX 0 C5 1 -0.182982 0.315594 0.773743 11.00000 0.03008 0.02555 = 0.02332 0.00833 0.00571 -0.00006 AFIX 43 H5 2 -0.317633 0.275657 0.802411 11.00000 -1.20000 AFIX 0 C3 1 0.099091 0.372763 0.612369 11.00000 0.02197 0.01877 = 0.01285 0.00233 0.00225 0.00454 C2 1 0.212971 0.434647 0.692168 11.00000 0.02839 0.01413 = 0.01821 -0.00145 0.00284 0.00165 AFIX 43 H2 2 0.345368 0.476231 0.665993 11.00000 -1.20000 AFIX 0 N1 3 0.131716 0.434454 0.807459 11.00000 0.03291 0.02516 = 0.01643 -0.00590 0.00026 -0.00087 C6 1 -0.063613 0.378679 0.849446 11.00000 0.02868 0.03139 = 0.01892 0.00310 0.00013 0.00351 AFIX 43 H6 2 -0.119202 0.382243 0.929329 11.00000 -1.20000 AFIX 0 H1 2 0.213241 0.467927 0.852343 11.00000 0.02642 HKLF 4 REM PRELIM 2 in P2(1)/c REM wR2 = 0.0803, GooF = S = 0.924, Restrained GooF = 0.924 for all data REM R1 = 0.0310 for 1524 Fo > 4sig(Fo) and 0.0347 for all 1683 data REM 78 parameters refined using 0 restraints END WGHT 0.0402 0.0000 REM Highest difference peak 1.228, deepest hole -1.566, 1-sigma level 0.198 Q1 1 0.3038 0.4307 0.1052 11.00000 0.05 1.23 Q2 1 0.2998 0.3880 0.2007 11.00000 0.05 1.17 Q3 1 0.5095 0.3901 0.0519 11.00000 0.05 1.09 Q4 1 0.1323 0.3737 0.5148 11.00000 0.05 1.07 Q5 1 0.4868 0.4356 0.1511 11.00000 0.05 0.99 Q6 1 0.1403 0.4187 0.4198 11.00000 0.05 0.96 Q7 1 0.3066 0.3475 0.1073 11.00000 0.05 0.93 Q8 1 0.3276 0.3336 0.4579 11.00000 0.05 0.92 Q9 1 0.1450 0.3318 0.4132 11.00000 0.05 0.90 Q10 1 0.2914 0.3739 0.3600 11.00000 0.05 0.89 Q11 1 0.6415 0.3904 0.1214 11.00000 0.05 0.76 Q12 1 0.2330 0.4159 0.4427 11.00000 0.05 0.74 Q13 1 -0.2902 0.3851 1.0052 11.00000 0.05 0.70 Q14 1 0.1633 0.3929 0.1343 11.00000 0.05 0.70 Q15 1 0.4965 0.3428 0.1544 11.00000 0.05 0.62 Q16 1 0.3628 0.2990 0.3815 11.00000 0.05 0.59 Q17 1 0.1881 0.4328 0.7544 11.00000 0.05 0.57 Q18 1 0.3534 0.4493 0.3810 11.00000 0.05 0.55 Q19 1 -0.1534 0.3795 0.5619 11.00000 0.05 0.54 Q20 1 0.4475 0.3712 0.4311 11.00000 0.05 0.54 ; _shelx_res_checksum 87365 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 0.40203(6) 0.38874(2) 0.12615(2) 0.02038(14) Uani 1 1 d . . . . . I2 I 0.22339(6) 0.37461(2) 0.43196(3) 0.02278(14) Uani 1 1 d . . . . . C4 C -0.1005(9) 0.3121(3) 0.6541(4) 0.0221(9) Uani 1 1 d . . . . . H4 H -0.178364 0.269470 0.602276 0.027 Uiso 1 1 calc R U . . . C5 C -0.1830(9) 0.3156(3) 0.7737(4) 0.0262(10) Uani 1 1 d . . . . . H5 H -0.317633 0.275657 0.802411 0.031 Uiso 1 1 calc R U . . . C3 C 0.0991(9) 0.3728(3) 0.6124(4) 0.0178(9) Uani 1 1 d . . . . . C2 C 0.2130(9) 0.4346(3) 0.6922(4) 0.0202(9) Uani 1 1 d . . . . . H2 H 0.345368 0.476231 0.665993 0.024 Uiso 1 1 calc R U . . . N1 N 0.1317(8) 0.4345(3) 0.8075(4) 0.0248(8) Uani 1 1 d . . . . . C6 C -0.0636(10) 0.3787(3) 0.8494(5) 0.0263(10) Uani 1 1 d . . . . . H6 H -0.119202 0.382243 0.929329 0.032 Uiso 1 1 calc R U . . . H1 H 0.213(10) 0.468(4) 0.852(5) 0.026(14) Uiso 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 I1 0.0264(2) 0.01857(19) 0.0164(2) -0.00054(11) 0.00369(12) 0.00000(9) I2 0.0318(2) 0.0205(2) 0.0162(2) -0.00111(11) 0.00504(13) -0.00269(10) C4 0.027(2) 0.018(2) 0.022(2) -0.0021(19) -0.0003(18) 0.0002(16) C5 0.030(2) 0.026(2) 0.023(2) 0.008(2) 0.006(2) -0.0001(17) C3 0.022(2) 0.019(2) 0.013(2) 0.0023(17) 0.0023(16) 0.0045(15) C2 0.028(2) 0.014(2) 0.018(2) -0.0014(19) 0.0028(17) 0.0017(16) N1 0.033(2) 0.025(2) 0.0164(19) -0.0059(18) 0.0003(16) -0.0009(16) C6 0.029(2) 0.031(3) 0.019(2) 0.003(2) 0.0001(19) 0.0035(18) 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 C3 C4 C5 119.6(4) . . ? C6 C5 C4 119.5(4) . . ? C4 C3 C2 118.7(4) . . ? C4 C3 I2 121.8(3) . . ? C2 C3 I2 119.5(3) . . ? N1 C2 C3 119.7(4) . . ? C6 N1 C2 123.0(4) . . ? N1 C6 C5 119.5(5) . . ? 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 C3 2.095(5) . ? C4 C3 1.390(6) . ? C4 C5 1.391(6) . ? C5 C6 1.377(7) . ? C3 C2 1.383(6) . ? C2 N1 1.341(6) . ? N1 C6 1.330(6) . ?