#------------------------------------------------------------------------------ #$Date: 2016-01-23 06:12:30 +0200 (Sat, 23 Jan 2016) $ #$Revision: 174815 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/39/7223960.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_7223960 loop_ _publ_author_name 'Vasylyeva, Vera' 'Catalano, Luca' 'Nervi, Carlo' 'Gobetto, Roberto' 'Metrangolo, Pierangelo' 'Resnati, Giuseppe' _publ_section_title ; Characteristic redshift and intensity enhancement as Far-IR fingerprints of the halogen bond involving aromatic donors ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/C5CE02385H _journal_year 2016 _chemical_formula_moiety 'C6 Br F5, C5 H5 N' _chemical_formula_sum 'C11 H5 Br F5 N' _chemical_formula_weight 326.06 _chemical_melting_point 254.15 _chemical_name_common 'bromopentafluorobenzene pyridine' _chemical_name_systematic 'bromopentafluorobenzene and pyridine (1:1)' _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' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2013 _audit_update_record ; 2015-10-23 deposited with the CCDC. 2016-01-12 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 101.4780(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.8544(4) _cell_length_b 9.3356(4) _cell_length_c 14.0154(6) _cell_measurement_reflns_used 4071 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 24.730 _cell_measurement_theta_min 3.205 _cell_volume 1135.36(9) _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _diffrn_ambient_temperature 173(2) _diffrn_measured_fraction_theta_full 0.972 _diffrn_measured_fraction_theta_max 0.995 _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0176 _diffrn_reflns_av_unetI/netI 0.0193 _diffrn_reflns_laue_measured_fraction_full 0.972 _diffrn_reflns_laue_measured_fraction_max 0.995 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 5249 _diffrn_reflns_point_group_measured_fraction_full 0.972 _diffrn_reflns_point_group_measured_fraction_max 0.995 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 24.998 _diffrn_reflns_theta_min 2.638 _exptl_absorpt_coefficient_mu 3.666 _exptl_absorpt_correction_T_max 0.7452 _exptl_absorpt_correction_T_min 0.5476 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details SADABS _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.908 _exptl_crystal_description cylindrical _exptl_crystal_F_000 632 _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _refine_diff_density_max 0.237 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.044 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 163 _refine_ls_number_reflns 1994 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.070 _refine_ls_R_factor_all 0.0199 _refine_ls_R_factor_gt 0.0183 _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^)+(0.0235P)^2^+0.4299P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0481 _refine_ls_wR_factor_ref 0.0487 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1868 _reflns_number_total 1994 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c5ce02385h2.cif _cod_data_source_block vv13_0m _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '-19' was changed to '254.15' - it was converted from degrees Celsius(C) to Kelvins(K). Automatic conversion script Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas ; _cod_database_code 7223960 _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. ; _shelxl_version_number 2013-4 _shelx_res_file ; TITL F016 - EXOR New: P21/c CELL 0.71073 8.8544 9.3356 14.0154 90.000 101.478 90.000 ZERR 1 0.0004 0.0004 0.0006 0.000 0.001 0.000 LATT 1 SYMM - X , 0.50000 + Y , 0.50000 - Z SFAC C 2.31000 20.84392 1.02000 10.20751 1.58860 0.56870 0.86500 = 51.65125 0.21560 0.00330 0.00160 11.500 0.68000 12.01000 SFAC H 0.49300 10.51091 0.32291 26.12573 0.14019 3.14236 0.04081 = 57.79977 0.00304 0.00000 0.00000 0.624 0.35000 1.00800 SFAC Br 17.17892 2.17230 5.23581 16.57962 5.63771 0.26090 3.98510 = 41.43285 2.95570 -0.29010 2.45950 10000.000 1.21000 79.90000 SFAC F 3.53920 10.28251 2.64120 4.29440 1.51700 0.26150 1.02430 = 26.14763 0.27760 0.01710 0.01030 51.500 0.64000 19.00000 SFAC N 12.21261 0.00570 3.13220 9.89331 2.01250 28.99754 1.16630 = 0.58260 -11.52901 0.00610 0.00330 19.600 0.68000 14.01000 UNIT 44 20 4 20 4 LIST 4 ! automatically inserted. Change 6 to 4 for CHECKCIF!! TEMP -100 omit -1 50.0 L.S. 12 FMAP 2 PLAN 1 ACTA conf HTAB BOND $H WGHT 0.023500 0.429900 FVAR 0.24612 BR1 3 -0.153858 0.294870 -0.107348 11.00000 0.03308 0.03695 = 0.02830 -0.00178 0.00457 -0.00380 C1 1 0.552811 0.326107 0.196247 11.00000 0.04080 0.04631 = 0.05562 -0.01817 0.01237 -0.01116 AFIX 43 H1 2 0.548159 0.378637 0.253644 11.00000 -1.20000 AFIX 0 N1 5 0.644327 0.210956 0.203982 11.00000 0.03624 0.05428 = 0.03773 -0.00159 -0.00242 0.00133 F1 4 -0.174135 0.475207 0.072166 11.00000 0.03564 0.03521 = 0.04400 -0.00263 0.00799 0.00815 F2 4 -0.005197 0.459295 0.253694 11.00000 0.05710 0.03898 = 0.03268 -0.00946 0.01519 -0.00089 C2 1 0.465385 0.372277 0.109827 11.00000 0.03369 0.03618 = 0.08312 0.01424 0.00674 -0.00210 AFIX 43 H2 2 0.402081 0.454828 0.107769 11.00000 -1.20000 AFIX 0 F3 4 0.220582 0.259414 0.298523 11.00000 0.05285 0.05406 = 0.02992 0.00522 -0.00217 -0.00014 C3 1 0.470721 0.297899 0.026931 11.00000 0.04479 0.06116 = 0.04972 0.02331 -0.00785 -0.02001 AFIX 43 H3 2 0.411553 0.327620 -0.033992 11.00000 -1.20000 AFIX 0 F4 4 0.277573 0.076935 0.159245 11.00000 0.04027 0.03675 = 0.05501 0.00988 0.00760 0.01024 C4 1 0.563306 0.179294 0.033383 11.00000 0.05999 0.05516 = 0.03698 -0.00831 0.01616 -0.02808 AFIX 43 H4 2 0.568778 0.124653 -0.023011 11.00000 -1.20000 AFIX 0 F5 4 0.114351 0.094806 -0.023722 11.00000 0.04424 0.03400 = 0.04161 -0.00853 0.01779 0.00152 C5 1 0.647777 0.140786 0.122353 11.00000 0.04176 0.03768 = 0.05358 0.00031 0.01341 0.00106 AFIX 43 H5 2 0.712570 0.059070 0.125742 11.00000 -1.20000 AFIX 0 C6 1 -0.035123 0.284578 0.019466 11.00000 0.02664 0.02749 = 0.02715 0.00041 0.00719 -0.00707 C7 1 -0.062984 0.375722 0.092152 11.00000 0.02657 0.02427 = 0.03432 0.00032 0.00975 -0.00099 C8 1 0.021727 0.367739 0.185519 11.00000 0.03664 0.02666 = 0.02833 -0.00348 0.01315 -0.00664 C9 1 0.136269 0.266744 0.208254 11.00000 0.03508 0.03274 = 0.02565 0.00475 0.00354 -0.00668 C10 1 0.165444 0.174595 0.137397 11.00000 0.02850 0.02533 = 0.04054 0.00798 0.00984 0.00017 C11 1 0.080958 0.184355 0.043911 11.00000 0.03008 0.02280 = 0.03207 -0.00317 0.01281 -0.00514 HKLF 4 REM F016 - EXOR New: P21/c REM R1 = 0.0183 for 1868 Fo > 4sig(Fo) and 0.0199 for all 1994 data REM 163 parameters refined using 0 restraints END WGHT 0.0235 0.4299 REM Instructions for potential hydrogen bonds EQIV $1 -x+1, y+1/2, -z+1/2 HTAB C1 F4_$1 EQIV $2 -x, -y+1, -z HTAB C2 Br1_$2 REM Highest difference peak 0.237, deepest hole -0.241, 1-sigma level 0.044 Q1 1 -0.1727 0.3541 -0.0628 11.00000 0.05 0.24 ; _shelx_res_checksum 11972 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 Br1 Br -0.15386(2) 0.29487(2) -0.10735(2) 0.03299(8) Uani 1 1 d . . C1 C 0.5528(2) 0.3261(2) 0.19625(17) 0.0472(5) Uani 1 1 d . . H1 H 0.5482 0.3786 0.2536 0.057 Uiso 1 1 calc R U N1 N 0.6443(2) 0.21096(19) 0.20398(13) 0.0441(4) Uani 1 1 d . . F1 F -0.17414(11) 0.47521(11) 0.07217(8) 0.0383(3) Uani 1 1 d . . F2 F -0.00520(13) 0.45930(11) 0.25369(7) 0.0421(3) Uani 1 1 d . . C2 C 0.4654(2) 0.3723(2) 0.1098(2) 0.0517(6) Uani 1 1 d . . H2 H 0.4021 0.4548 0.1078 0.062 Uiso 1 1 calc R U F3 F 0.22058(14) 0.25941(14) 0.29852(8) 0.0470(3) Uani 1 1 d . . C3 C 0.4707(3) 0.2979(3) 0.02693(18) 0.0543(6) Uani 1 1 d . . H3 H 0.4116 0.3276 -0.0340 0.065 Uiso 1 1 calc R U F4 F 0.27757(12) 0.07693(12) 0.15924(9) 0.0443(3) Uani 1 1 d . . C4 C 0.5633(3) 0.1793(3) 0.03338(16) 0.0498(6) Uani 1 1 d . . H4 H 0.5688 0.1247 -0.0230 0.060 Uiso 1 1 calc R U F5 F 0.11435(12) 0.09481(12) -0.02372(8) 0.0387(3) Uani 1 1 d . . C5 C 0.6478(2) 0.1408(2) 0.12235(16) 0.0438(5) Uani 1 1 d . . H5 H 0.7126 0.0591 0.1257 0.053 Uiso 1 1 calc R U C6 C -0.03512(19) 0.28458(17) 0.01947(13) 0.0268(4) Uani 1 1 d . . C7 C -0.06298(18) 0.37572(18) 0.09215(13) 0.0279(4) Uani 1 1 d . . C8 C 0.0217(2) 0.36774(18) 0.18552(12) 0.0296(4) Uani 1 1 d . . C9 C 0.1363(2) 0.2667(2) 0.20825(13) 0.0315(4) Uani 1 1 d . . C10 C 0.1654(2) 0.17460(19) 0.13740(14) 0.0310(4) Uani 1 1 d . . C11 C 0.08096(19) 0.18436(18) 0.04391(13) 0.0274(4) 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 Br1 0.03308(12) 0.03695(13) 0.02830(12) -0.00178(7) 0.00457(8) -0.00380(7) C1 0.0408(11) 0.0463(12) 0.0556(14) -0.0182(10) 0.0124(10) -0.0112(9) N1 0.0362(9) 0.0543(11) 0.0377(10) -0.0016(8) -0.0024(7) 0.0013(8) F1 0.0356(5) 0.0352(6) 0.0440(6) -0.0026(5) 0.0080(5) 0.0081(5) F2 0.0571(7) 0.0390(6) 0.0327(6) -0.0095(5) 0.0152(5) -0.0009(5) C2 0.0337(10) 0.0362(12) 0.0831(18) 0.0142(11) 0.0067(11) -0.0021(9) F3 0.0529(7) 0.0541(7) 0.0299(6) 0.0052(5) -0.0022(5) -0.0001(6) C3 0.0448(12) 0.0612(15) 0.0497(14) 0.0233(11) -0.0078(10) -0.0200(11) F4 0.0403(6) 0.0367(6) 0.0550(7) 0.0099(5) 0.0076(5) 0.0102(5) C4 0.0600(14) 0.0552(14) 0.0370(11) -0.0083(10) 0.0162(10) -0.0281(12) F5 0.0442(6) 0.0340(6) 0.0416(6) -0.0085(5) 0.0178(5) 0.0015(5) C5 0.0418(11) 0.0377(11) 0.0536(13) 0.0003(9) 0.0134(9) 0.0011(9) C6 0.0266(8) 0.0275(9) 0.0272(9) 0.0004(7) 0.0072(7) -0.0071(7) C7 0.0266(8) 0.0243(9) 0.0343(9) 0.0003(7) 0.0098(7) -0.0010(7) C8 0.0366(9) 0.0267(9) 0.0283(9) -0.0035(7) 0.0131(7) -0.0066(7) C9 0.0351(10) 0.0327(9) 0.0257(9) 0.0047(7) 0.0035(7) -0.0067(8) C10 0.0285(9) 0.0253(9) 0.0405(10) 0.0080(8) 0.0098(7) 0.0002(7) C11 0.0301(9) 0.0228(8) 0.0321(9) -0.0032(7) 0.0128(7) -0.0051(7) 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle N1 C1 C2 123.4(2) N1 C1 H1 118.3 C2 C1 H1 118.3 C5 N1 C1 116.45(19) C3 C2 C1 118.9(2) C3 C2 H2 120.5 C1 C2 H2 120.5 C2 C3 C4 118.5(2) C2 C3 H3 120.7 C4 C3 H3 120.7 C5 C4 C3 118.9(2) C5 C4 H4 120.5 C3 C4 H4 120.5 N1 C5 C4 123.7(2) N1 C5 H5 118.1 C4 C5 H5 118.1 C11 C6 C7 117.76(16) C11 C6 Br1 121.19(13) C7 C6 Br1 121.05(13) F1 C7 C8 118.35(15) F1 C7 C6 120.12(15) C8 C7 C6 121.53(16) F2 C8 C7 120.27(16) F2 C8 C9 120.03(16) C7 C8 C9 119.69(16) F3 C9 C8 120.12(17) F3 C9 C10 120.08(17) C8 C9 C10 119.80(17) F4 C10 C11 120.07(17) F4 C10 C9 119.87(17) C11 C10 C9 120.06(16) F5 C11 C10 118.51(16) F5 C11 C6 120.33(16) C10 C11 C6 121.16(16) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Br1 C6 1.8788(18) C1 N1 1.338(3) C1 C2 1.371(3) C1 H1 0.9500 N1 C5 1.324(3) F1 C7 1.3416(19) F2 C8 1.338(2) C2 C3 1.362(4) C2 H2 0.9500 F3 C9 1.337(2) C3 C4 1.370(4) C3 H3 0.9500 F4 C10 1.338(2) C4 C5 1.368(3) C4 H4 0.9500 F5 C11 1.340(2) C5 H5 0.9500 C6 C11 1.382(2) C6 C7 1.387(2) C7 C8 1.375(3) C8 C9 1.375(3) C9 C10 1.377(3) C10 C11 1.376(3) loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion C2 C1 N1 C5 0.1(3) N1 C1 C2 C3 0.1(3) C1 C2 C3 C4 0.2(3) C2 C3 C4 C5 -0.6(3) C1 N1 C5 C4 -0.5(3) C3 C4 C5 N1 0.8(3) C11 C6 C7 F1 179.82(14) Br1 C6 C7 F1 -1.3(2) C11 C6 C7 C8 0.2(2) Br1 C6 C7 C8 179.05(13) F1 C7 C8 F2 -1.2(2) C6 C7 C8 F2 178.41(14) F1 C7 C8 C9 179.90(15) C6 C7 C8 C9 -0.5(3) F2 C8 C9 F3 0.2(3) C7 C8 C9 F3 179.12(15) F2 C8 C9 C10 -178.77(15) C7 C8 C9 C10 0.1(3) F3 C9 C10 F4 0.5(3) C8 C9 C10 F4 179.53(15) F3 C9 C10 C11 -178.50(16) C8 C9 C10 C11 0.5(3) F4 C10 C11 F5 -0.3(2) C9 C10 C11 F5 178.73(15) F4 C10 C11 C6 -179.81(15) C9 C10 C11 C6 -0.8(3) C7 C6 C11 F5 -179.08(14) Br1 C6 C11 F5 2.1(2) C7 C6 C11 C10 0.4(2) Br1 C6 C11 C10 -178.42(13)