#------------------------------------------------------------------------------ #$Date: 2020-05-13 04:35:15 +0300 (Wed, 13 May 2020) $ #$Revision: 252006 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/05/7240510.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_7240510 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 11 _space_group_name_Hall '-P 2yb' _space_group_name_H-M_alt 'P 1 21/m 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 95.160(6) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 4.3789(3) _cell_length_b 8.5332(7) _cell_length_c 9.9405(6) _cell_measurement_reflns_used 1476 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 35.4432 _cell_measurement_theta_min 4.0975 _cell_volume 369.93(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 ; 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 0.990 _diffrn_measured_fraction_theta_max 0.987 _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 0.0818 _diffrn_reflns_av_unetI/netI 0.0663 _diffrn_reflns_Laue_measured_fraction_full 0.990 _diffrn_reflns_Laue_measured_fraction_max 0.987 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_number 1659 _diffrn_reflns_point_group_measured_fraction_full 0.990 _diffrn_reflns_point_group_measured_fraction_max 0.987 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.998 _diffrn_reflns_theta_min 4.117 _diffrn_source 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 9.629 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.15441 _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 2.567 _exptl_crystal_description needle _exptl_crystal_F_000 260 _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.08 _refine_diff_density_max 1.574 _refine_diff_density_min -2.093 _refine_diff_density_rms 0.291 _refine_ls_extinction_coef 0.101(11) _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 1.063 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 30 _refine_ls_number_reflns 855 _refine_ls_number_restraints 19 _refine_ls_restrained_S_all 1.052 _refine_ls_R_factor_all 0.0611 _refine_ls_R_factor_gt 0.0570 _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^)+(0.1094P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1550 _refine_ls_wR_factor_ref 0.1573 _reflns_Friedel_coverage 0.000 _reflns_number_gt 754 _reflns_number_total 855 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ce00534g2.cif _cod_data_source_block 4-IPyHBr _cod_original_sg_symbol_H-M 'P 21/m' _cod_database_code 7240510 _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 P2(1)/m shelx.res created by SHELXL-2018/3 at 11:14:17 on 15-Oct-2019 CELL 0.71073 4.3789 8.5332 9.9405 90.000 95.160 90.000 ZERR 2.00 0.0003 0.0007 0.0006 0.000 0.006 0.000 LATT 1 SYMM - X, 1/2 + Y, - Z SFAC C H N BR I UNIT 10 10 2 2 2 MERG 2 OMIT -4.00 54.00 OMIT 1 8 7 DELU 0.010 0.010 C3 C2 SIMU 0.040 0.080 1.700 C3 C2 DELU 0.010 0.010 C4 N1 SIMU 0.040 0.080 1.700 C4 N1 ISOR 0.100 C4 N1 EADP C3 C2 ISOR 0.050 C4 N1 FMAP 2 PLAN 20 ACTA BOND LIST 6 L.S. 40 WGHT 0.109400 EXTI 0.100528 FVAR 8.81049 I1 5 0.145045 0.750000 1.043435 10.50000 0.04454 0.04890 = 0.03127 0.00000 0.00925 0.00000 BR1 4 0.979129 0.750000 0.366146 10.50000 0.05055 0.05539 = 0.03227 0.00000 0.01345 0.00000 C4 1 0.323970 0.750000 0.853433 10.50000 10.03014 10.04941 = 10.02240 10.00000 9.99247 10.00000 N1 3 0.603218 0.750000 0.625453 10.50000 10.04927 10.07263 = 10.01895 10.00000 9.99316 10.00000 AFIX 43 H1 2 0.694822 0.749999 0.552469 10.50000 -1.20000 AFIX 0 C3 1 0.388273 0.612332 0.796074 11.00000 0.05770 0.04828 = 0.03576 -0.00330 0.00349 0.00373 AFIX 43 H3 2 0.333964 0.518282 0.834751 11.00000 -1.20000 AFIX 0 C2 1 0.536674 0.612709 0.678473 11.00000 0.05770 0.04828 = 0.03576 -0.00330 0.00349 0.00373 AFIX 43 H2 2 0.588131 0.519320 0.637892 11.00000 -1.20000 AFIX 0 HKLF 4 REM shelxt_a.res in P2(1)/m REM wR2 = 0.1573, GooF = S = 1.063, Restrained GooF = 1.052 for all data REM R1 = 0.0570 for 754 Fo > 4sig(Fo) and 0.0611 for all 855 data REM 30 parameters refined using 19 restraints END WGHT 0.1086 0.0000 REM Highest difference peak 1.574, deepest hole -2.093, 1-sigma level 0.291 Q1 1 0.2148 0.7500 0.9227 10.50000 0.05 1.57 Q2 1 0.2199 0.8350 0.9964 11.00000 0.05 1.43 Q3 1 0.4011 0.7500 1.0159 10.50000 0.05 1.38 Q4 1 -0.1190 0.7500 1.0689 10.50000 0.05 1.34 Q5 1 0.0765 0.7500 1.1630 10.50000 0.05 1.09 Q6 1 0.8774 0.8407 0.4106 11.00000 0.05 1.01 Q7 1 0.0338 0.8563 1.0884 11.00000 0.05 0.89 Q8 1 1.2293 0.7500 0.3413 10.50000 0.05 0.88 Q9 1 1.0490 0.7500 0.2438 10.50000 0.05 0.86 Q10 1 1.0660 0.8472 0.3225 11.00000 0.05 0.81 Q11 1 0.9050 0.7500 0.4857 10.50000 0.05 0.81 Q12 1 0.1390 0.9005 1.0431 11.00000 0.05 0.76 Q13 1 0.2441 0.5737 0.9372 11.00000 0.05 0.69 Q14 1 -0.0474 0.7500 0.9472 10.50000 0.05 0.67 Q15 1 0.6644 0.7500 0.6649 10.50000 0.05 0.66 Q16 1 0.8671 0.9332 0.4716 11.00000 0.05 0.64 Q17 1 0.4610 0.7500 1.2207 10.50000 0.05 0.64 Q18 1 0.3309 0.7500 1.1458 10.50000 0.05 0.64 Q19 1 -0.1089 0.9554 0.9929 11.00000 0.05 0.61 Q20 1 0.7111 0.7500 0.3930 10.50000 0.05 0.60 ; _shelx_res_checksum 84094 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, 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 I1 I 0.14504(14) 0.750000 1.04344(6) 0.0412(4) Uani 1 2 d S T P . . Br1 Br 0.9791(3) 0.750000 0.36615(10) 0.0455(4) Uani 1 2 d S T P . . C4 C 0.324(2) 0.750000 0.8534(9) 0.035 Uani 1 2 d S TU P . . N1 N 0.603(2) 0.750000 0.6255(8) 0.048 Uani 1 2 d S TU P . . H1 H 0.694822 0.749999 0.552469 0.057 Uiso 1 2 calc R U P . . C3 C 0.3883(18) 0.6123(10) 0.7961(7) 0.0473(12) Uani 1 1 d . U . . . H3 H 0.333964 0.518282 0.834751 0.057 Uiso 1 1 calc R U . . . C2 C 0.5367(18) 0.6127(10) 0.6785(8) 0.0473(12) Uani 1 1 d . U . . . H2 H 0.588131 0.519320 0.637892 0.057 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 0.0445(5) 0.0489(6) 0.0313(5) 0.000 0.0093(3) 0.000 Br1 0.0505(7) 0.0554(8) 0.0323(6) 0.000 0.0135(4) 0.000 C4 0.030 0.049 0.022 0.000 -0.008 0.000 N1 0.049 0.073 0.019 0.000 -0.007 0.000 C3 0.058(3) 0.048(3) 0.036(3) -0.003(2) 0.003(2) 0.004(2) C2 0.058(3) 0.048(3) 0.036(3) -0.003(2) 0.003(2) 0.004(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 C3 C4 C3 121.5(10) 4_575 . ? C3 C4 I1 119.2(5) 4_575 . ? C3 C4 I1 119.2(5) . . ? C2 N1 C2 123.9(10) 4_575 . ? C4 C3 C2 119.1(9) . . ? N1 C2 C3 118.2(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 I1 C4 2.109(10) . ? C4 C3 1.347(9) 4_575 ? C4 C3 1.347(9) . ? N1 C2 1.328(9) 4_575 ? N1 C2 1.328(9) . ? C3 C2 1.388(11) . ?