#------------------------------------------------------------------------------ #$Date: 2020-05-13 04:35:15 +0300 (Wed, 13 May 2020) $ #$Revision: 252006 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/05/7240509.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_7240509 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 Cl I N' _chemical_formula_weight 241.45 _space_group_crystal_system monoclinic _space_group_IT_number 13 _space_group_name_Hall '-P 2yc' _space_group_name_H-M_alt 'P 1 2/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 90.518(8) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.5864(11) _cell_length_b 4.3468(5) _cell_length_c 15.0822(14) _cell_measurement_reflns_used 1271 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 69.9210 _cell_measurement_theta_min 4.1050 _cell_volume 694.01(13) _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _diffrn_ambient_temperature 298(2) _diffrn_detector_area_resol_mean 10.4323 _diffrn_measured_fraction_theta_full 0.987 _diffrn_measured_fraction_theta_max 0.967 _diffrn_measurement_device_type 'Xcalibur, Ruby, Nova' _diffrn_measurement_method '\w scan' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0357 _diffrn_reflns_av_unetI/netI 0.0427 _diffrn_reflns_Laue_measured_fraction_full 0.987 _diffrn_reflns_Laue_measured_fraction_max 0.967 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 2838 _diffrn_reflns_point_group_measured_fraction_full 0.987 _diffrn_reflns_point_group_measured_fraction_max 0.967 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 76.418 _diffrn_reflns_theta_min 4.176 _diffrn_source 'micro-focus sealed X-ray tube' _exptl_absorpt_coefficient_mu 38.942 _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 2.311 _exptl_crystal_description needle _exptl_crystal_F_000 448 _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_transmission_factor_max 2.564 _exptl_transmission_factor_min 0.472 _refine_diff_density_max 1.530 _refine_diff_density_min -1.333 _refine_diff_density_rms 0.219 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.116 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 73 _refine_ls_number_reflns 1423 _refine_ls_number_restraints 6 _refine_ls_restrained_S_all 1.118 _refine_ls_R_factor_all 0.0564 _refine_ls_R_factor_gt 0.0506 _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^)+(0.0892P)^2^+0.4203P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1370 _refine_ls_wR_factor_ref 0.1498 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1244 _reflns_number_total 1423 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ce00534g2.cif _cod_data_source_block 3-IPyHCl _cod_original_sg_symbol_H-M 'P 2/c' _cod_database_code 7240509 _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 2/c shelx.res created by SHELXL-2018/3 at 10:25:43 on 04-Mar-2020 CELL 1.54184 10.5864 4.3468 15.0822 90.000 90.518 90.000 ZERR 4.00 0.0011 0.0005 0.0014 0.000 0.008 0.000 LATT 1 SYMM - X, Y, 1/2 - Z SFAC C H N CL I UNIT 20 20 4 4 4 MERG 2 OMIT -4.00 180.00 OMIT 12 1 3 OMIT 13 0 0 OMIT -10 1 11 ISOR 0.010 0.20 C5 FMAP 2 PLAN 20 ACTA BOND L.S. 34 TEMP 25.00 WGHT 0.089200 0.420300 FVAR 3.84189 N1 3 1.311855 -0.179377 0.688735 11.00000 0.05173 0.04977 = 0.04926 0.00135 -0.00987 0.00832 AFIX 43 H1 2 1.336121 -0.305248 0.729451 11.00000 -1.20000 AFIX 0 C3 1 1.147919 0.090696 0.618525 11.00000 0.02738 0.05522 = 0.04714 -0.00104 0.00082 0.00689 C4 1 1.232550 0.202328 0.557077 11.00000 0.04682 0.05091 = 0.04247 0.00223 0.00100 0.00425 AFIX 43 H4 2 1.205224 0.324056 0.509961 11.00000 -1.20000 AFIX 0 C5 1 1.361575 0.126733 0.567703 11.00000 0.02996 0.07168 = 0.06642 -0.00213 0.01162 0.00079 AFIX 43 H5 2 1.421214 0.210010 0.529689 11.00000 -1.20000 AFIX 0 C2 1 1.190243 -0.107085 0.684374 11.00000 0.04045 0.04765 = 0.04422 -0.00223 -0.00262 0.00305 AFIX 43 H2 2 1.133935 -0.188410 0.725138 11.00000 -1.20000 AFIX 0 C6 1 1.398638 -0.068892 0.633900 11.00000 0.04400 0.06881 = 0.06161 -0.00483 0.00176 0.01392 AFIX 43 H6 2 1.483084 -0.123953 0.640544 11.00000 -1.20000 AFIX 0 MOLE 1 I1 5 0.957186 0.221152 0.618069 11.00000 0.03792 0.05417 = 0.04425 0.00265 -0.00133 0.00539 CL1 4 1.334693 -1.417047 0.352070 11.00000 0.03996 0.05647 = 0.06247 -0.00312 -0.00210 0.00238 HKLF 4 REM SIR92 run in space group P 2/c REM wR2 = 0.1498, GooF = S = 1.116, Restrained GooF = 1.118 for all data REM R1 = 0.0506 for 1244 Fo > 4sig(Fo) and 0.0564 for all 1423 data REM 73 parameters refined using 6 restraints END WGHT 0.0895 0.4359 REM Highest difference peak 1.530, deepest hole -1.333, 1-sigma level 0.219 Q1 1 0.9360 -0.0230 0.6191 11.00000 0.05 1.53 Q2 1 0.9660 0.4783 0.6142 11.00000 0.05 1.51 Q3 1 0.9809 0.2372 0.6946 11.00000 0.05 0.75 Q4 1 0.8578 0.2291 0.6446 11.00000 0.05 0.71 Q5 1 0.9470 0.2182 0.5441 11.00000 0.05 0.71 Q6 1 1.2267 -1.3989 0.3845 11.00000 0.05 0.65 Q7 1 1.3715 -1.4147 0.3393 11.00000 0.05 0.59 Q8 1 1.1234 -0.2246 0.6404 11.00000 0.05 0.56 Q9 1 1.0093 -0.1568 0.5274 11.00000 0.05 0.55 Q10 1 1.3431 -1.2446 0.3360 11.00000 0.05 0.54 Q11 1 1.3043 -1.6413 0.3672 11.00000 0.05 0.54 Q12 1 1.0561 0.2168 0.5909 11.00000 0.05 0.53 Q13 1 1.0403 0.4937 0.4918 11.00000 0.05 0.51 Q14 1 1.0411 -0.2651 0.8348 11.00000 0.05 0.48 Q15 1 1.2370 0.1159 0.5905 11.00000 0.05 0.47 Q16 1 1.3820 -0.3775 0.8030 11.00000 0.05 0.46 Q17 1 1.3284 -1.0623 0.3532 11.00000 0.05 0.46 Q18 1 1.3271 -0.0606 0.6734 11.00000 0.05 0.46 Q19 1 1.2280 -1.0509 0.3819 11.00000 0.05 0.43 Q20 1 1.2458 0.3103 0.5826 11.00000 0.05 0.43 ; _shelx_res_checksum 94122 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -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 N1 N 1.3119(7) -0.1794(18) 0.6887(5) 0.0503(16) Uani 1 1 d . . . . . H1 H 1.336121 -0.305248 0.729451 0.060 Uiso 1 1 calc R U . . . C3 C 1.1479(6) 0.091(2) 0.6185(5) 0.0432(16) Uani 1 1 d . . . . . C4 C 1.2326(8) 0.202(2) 0.5571(6) 0.0467(18) Uani 1 1 d . . . . . H4 H 1.205224 0.324056 0.509961 0.056 Uiso 1 1 calc R U . . . C5 C 1.3616(7) 0.127(3) 0.5677(6) 0.056(2) Uani 1 1 d . U . . . H5 H 1.421214 0.210010 0.529689 0.067 Uiso 1 1 calc R U . . . C2 C 1.1902(7) -0.107(2) 0.6844(5) 0.0441(16) Uani 1 1 d . . . . . H2 H 1.133935 -0.188410 0.725138 0.053 Uiso 1 1 calc R U . . . C6 C 1.3986(8) -0.069(3) 0.6339(6) 0.058(2) Uani 1 1 d . . . . . H6 H 1.483084 -0.123953 0.640544 0.070 Uiso 1 1 calc R U . . . I1 I 0.95719(4) 0.22115(13) 0.61807(3) 0.0455(3) Uani 1 1 d . . . . . Cl1 Cl 1.33469(17) -1.4170(6) 0.35207(14) 0.0530(5) 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 N1 0.052(4) 0.050(4) 0.049(4) 0.001(3) -0.010(3) 0.008(3) C3 0.027(3) 0.055(5) 0.047(3) -0.001(3) 0.001(2) 0.007(3) C4 0.047(4) 0.051(5) 0.042(4) 0.002(3) 0.001(3) 0.004(3) C5 0.030(3) 0.072(5) 0.066(4) -0.002(4) 0.012(3) 0.001(4) C2 0.040(3) 0.048(4) 0.044(4) -0.002(3) -0.003(3) 0.003(3) C6 0.044(4) 0.069(6) 0.062(5) -0.005(5) 0.002(3) 0.014(4) I1 0.0379(3) 0.0542(4) 0.0443(4) 0.00265(19) -0.0013(2) 0.00539(18) Cl1 0.0400(8) 0.0565(13) 0.0625(11) -0.0031(9) -0.0021(7) 0.0024(8) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.3257 6.8362 '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 124.0(8) . . ? C4 C3 C2 119.4(7) . . ? C4 C3 I1 122.2(6) . . ? C2 C3 I1 118.4(5) . . ? C3 C4 C5 118.3(8) . . ? C6 C5 C4 119.9(8) . . ? N1 C2 C3 119.4(7) . . ? N1 C6 C5 118.9(8) . . ? 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 N1 C2 1.326(11) . ? N1 C6 1.331(13) . ? C3 C4 1.383(11) . ? C3 C2 1.385(12) . ? C3 I1 2.097(6) . ? C4 C5 1.413(12) . ? C5 C6 1.366(15) . ?