#------------------------------------------------------------------------------ #$Date: 2020-05-13 04:35:15 +0300 (Wed, 13 May 2020) $ #$Revision: 252006 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/05/7240507.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_7240507 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 orthorhombic _space_group_IT_number 29 _space_group_name_Hall 'P 2c -2ac' _space_group_name_H-M_alt 'P c a 21' _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 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 14.9620(7) _cell_length_b 4.5454(2) _cell_length_c 10.9014(5) _cell_measurement_reflns_used 2649 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 36.4733 _cell_measurement_theta_min 3.9724 _cell_volume 741.39(6) _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 0.993 _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 0.0414 _diffrn_reflns_av_unetI/netI 0.0400 _diffrn_reflns_Laue_measured_fraction_full 0.993 _diffrn_reflns_Laue_measured_fraction_max 0.994 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 4389 _diffrn_reflns_point_group_measured_fraction_full 0.960 _diffrn_reflns_point_group_measured_fraction_max 0.960 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.993 _diffrn_reflns_theta_min 4.484 _diffrn_source 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 9.609 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.28909 _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 2.561 _exptl_crystal_description needle _exptl_crystal_F_000 520 _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.12 _refine_diff_density_max 0.538 _refine_diff_density_min -0.775 _refine_diff_density_rms 0.139 _refine_ls_abs_structure_details ; Refined as an inversion twin. ; _refine_ls_abs_structure_Flack 0.11(3) _refine_ls_extinction_coef 0.0354(16) _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 0.880 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 75 _refine_ls_number_reflns 1548 _refine_ls_number_restraints 15 _refine_ls_restrained_S_all 0.876 _refine_ls_R_factor_all 0.0359 _refine_ls_R_factor_gt 0.0287 _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^)+(0.0387P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0613 _refine_ls_wR_factor_ref 0.0625 _reflns_Friedel_coverage 0.832 _reflns_Friedel_fraction_full 0.922 _reflns_Friedel_fraction_max 0.921 _reflns_number_gt 1228 _reflns_number_total 1548 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ce00534g2.cif _cod_data_source_block 2-IPyHBr _cod_database_code 7240507 _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 shelxt_a.res in Pca2(1) shelx.res created by SHELXL-2018/3 at 10:30:54 on 15-Oct-2019 CELL 0.71073 14.9620 4.5454 10.9014 90.000 90.000 90.000 ZERR 4.00 0.0007 0.0002 0.0005 0.000 0.000 0.000 LATT -1 SYMM - X, - Y, 1/2 + Z SYMM 1/2 + X, - Y, Z SYMM 1/2 - X, Y, 1/2 + Z SFAC C H N BR I UNIT 20 20 4 4 4 MERG 2 OMIT -4.00 54.00 omit 4 0 0 omit 0 0 4 omit 0 0 -4 TWIN DELU 0.010 0.010 C4 C5 SIMU 0.040 0.080 1.700 C4 C5 DELU 0.010 0.010 C3 C6 SIMU 0.040 0.080 1.700 C3 C6 DELU 0.010 0.010 C2 C3 C6 SIMU 0.040 0.080 1.700 C2 C3 C6 FMAP 2 PLAN 20 ACTA BOND LIST 6 L.S. 30 WGHT 0.038700 EXTI 0.035393 BASF 0.11185 FVAR 4.54954 I1 5 0.621726 0.741327 0.714064 11.00000 0.04126 0.05055 = 0.04149 -0.00353 -0.00316 -0.00018 BR1 4 0.401992 1.108095 0.505261 11.00000 0.05262 0.05817 = 0.04159 0.00141 0.00175 0.01195 C2 1 0.631475 0.606493 0.530007 11.00000 0.02749 0.04005 = 0.04423 0.00181 -0.00052 -0.00646 C3 1 0.695421 0.411207 0.491361 11.00000 0.03566 0.05644 = 0.04969 0.00315 0.00290 0.00241 AFIX 43 H3 2 0.738029 0.338429 0.545556 11.00000 -1.20000 AFIX 0 N1 3 0.572342 0.714338 0.449513 11.00000 0.02930 0.04544 = 0.04270 -0.00511 -0.00040 -0.00579 AFIX 43 H1 2 0.532477 0.836178 0.474988 11.00000 -1.20000 AFIX 0 C4 1 0.694853 0.324545 0.368466 11.00000 0.03554 0.06276 = 0.06109 -0.00490 0.01348 0.00103 AFIX 43 H4 2 0.735712 0.185113 0.341022 11.00000 -1.20000 AFIX 0 C6 1 0.573087 0.639812 0.331780 11.00000 0.04348 0.05347 = 0.04465 0.00020 -0.00748 -0.00658 AFIX 43 H6 2 0.531450 0.721784 0.278451 11.00000 -1.20000 AFIX 0 C5 1 0.634687 0.443234 0.288343 11.00000 0.05085 0.07371 = 0.04542 -0.00830 0.01043 -0.01425 AFIX 43 H5 2 0.635560 0.391447 0.205820 11.00000 -1.20000 AFIX 0 HKLF 4 REM shelxt_a.res in Pca2(1) REM wR2 = 0.0625, GooF = S = 0.880, Restrained GooF = 0.876 for all data REM R1 = 0.0287 for 1228 Fo > 4sig(Fo) and 0.0359 for all 1548 data REM 75 parameters refined using 15 restraints END WGHT 0.0360 0.0000 REM Highest difference peak 0.538, deepest hole -0.775, 1-sigma level 0.139 Q1 1 0.6193 0.5214 0.7132 11.00000 0.05 0.54 Q2 1 0.6184 0.9612 0.7264 11.00000 0.05 0.51 Q3 1 0.6180 0.8854 0.7716 11.00000 0.05 0.51 Q4 1 0.4047 1.2546 0.4428 11.00000 0.05 0.50 Q5 1 0.3992 0.8981 0.5036 11.00000 0.05 0.48 Q6 1 0.6217 0.6010 0.6389 11.00000 0.05 0.43 Q7 1 0.4069 1.3427 0.5122 11.00000 0.05 0.41 Q8 1 0.6213 0.6012 0.7828 11.00000 0.05 0.40 Q9 1 0.6614 0.2484 0.2197 11.00000 0.05 0.40 Q10 1 0.5887 0.8449 0.2346 11.00000 0.05 0.40 Q11 1 0.6373 0.4070 0.5053 11.00000 0.05 0.37 Q12 1 0.4725 0.9721 0.2973 11.00000 0.05 0.37 Q13 1 0.5955 0.6619 0.2074 11.00000 0.05 0.36 Q14 1 0.3995 1.0226 0.4278 11.00000 0.05 0.36 Q15 1 0.7797 0.1963 0.3886 11.00000 0.05 0.36 Q16 1 0.4110 0.9779 0.5869 11.00000 0.05 0.35 Q17 1 0.6113 0.7963 0.8612 11.00000 0.05 0.35 Q18 1 0.6217 0.2584 0.7156 11.00000 0.05 0.34 Q19 1 0.7927 -0.0065 0.3032 11.00000 0.05 0.33 Q20 1 0.7060 0.4834 0.6154 11.00000 0.05 0.33 ; _shelx_res_checksum 81695 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, 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 I1 I 0.62173(3) 0.74133(13) 0.71406(10) 0.0444(2) Uani 1 1 d . . . . . Br1 Br 0.40199(6) 1.10810(18) 0.50526(11) 0.0508(3) Uani 1 1 d . . . . . C2 C 0.6315(5) 0.6065(19) 0.5300(8) 0.037(2) Uani 1 1 d . U . . . C3 C 0.6954(6) 0.4112(16) 0.4914(11) 0.047(2) Uani 1 1 d . U . . . H3 H 0.738029 0.338429 0.545556 0.057 Uiso 1 1 calc R U . . . N1 N 0.5723(5) 0.7143(14) 0.4495(7) 0.0391(17) Uani 1 1 d . . . . . H1 H 0.532477 0.836178 0.474988 0.047 Uiso 1 1 calc R U . . . C4 C 0.6949(7) 0.325(2) 0.3685(9) 0.053(2) Uani 1 1 d . U . . . H4 H 0.735712 0.185113 0.341022 0.064 Uiso 1 1 calc R U . . . C6 C 0.5731(7) 0.640(2) 0.3318(9) 0.047(2) Uani 1 1 d . . . . . H6 H 0.531450 0.721784 0.278451 0.057 Uiso 1 1 calc R U . . . C5 C 0.6347(7) 0.443(2) 0.2883(9) 0.057(3) Uani 1 1 d . U . . . H5 H 0.635560 0.391447 0.205820 0.068 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 0.0413(3) 0.0506(3) 0.0415(3) -0.0035(3) -0.0032(3) -0.0002(3) Br1 0.0526(5) 0.0582(5) 0.0416(4) 0.0014(6) 0.0018(6) 0.0119(4) C2 0.027(4) 0.040(4) 0.044(6) 0.002(4) -0.001(3) -0.006(3) C3 0.036(4) 0.056(5) 0.050(5) 0.003(5) 0.003(5) 0.002(4) N1 0.029(4) 0.045(4) 0.043(4) -0.005(3) 0.000(3) -0.006(3) C4 0.036(5) 0.063(6) 0.061(6) -0.005(4) 0.013(4) 0.001(4) C6 0.043(6) 0.053(5) 0.045(5) 0.000(5) -0.007(4) -0.007(4) C5 0.051(6) 0.074(7) 0.045(5) -0.008(5) 0.010(4) -0.014(5) 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 N1 C2 C3 119.8(8) . . ? N1 C2 I1 118.2(6) . . ? C3 C2 I1 122.0(7) . . ? C2 C3 C4 118.2(9) . . ? C6 N1 C2 122.3(8) . . ? C5 C4 C3 120.4(9) . . ? N1 C6 C5 120.5(9) . . ? C4 C5 C6 118.7(10) . . ? 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 C2 2.103(8) . ? C2 N1 1.339(11) . ? C2 C3 1.371(12) . ? C3 C4 1.396(16) . ? N1 C6 1.327(12) . ? C4 C5 1.365(15) . ? C6 C5 1.368(14) . ?