#------------------------------------------------------------------------------ #$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2010543.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2010543 loop_ _publ_author_name 'Ramos Silva, M.' 'Paix\~ao, J. A.' 'Matos Beja, A.' 'Alte da Veiga, L.' _publ_section_title ; Very short F---H···F hydrogen bond in L-argininium fluoride hydrogen fluoride ; _journal_issue 1 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 104 _journal_page_last 106 _journal_volume 56 _journal_year 2000 _chemical_formula_moiety 'C6 H15 N4 O2 1+ , F 1- , HF' _chemical_formula_sum 'C6 H16 F2 N4 O2' _chemical_formula_weight 214.23 _chemical_name_systematic ; L-argininium fluoride hydrogen fluoride ; _space_group_IT_number 1 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall 'P 1' _symmetry_space_group_name_H-M 'P 1' _audit_creation_method SHELXL-97 _cell_angle_alpha 87.878(14) _cell_angle_beta 74.948(16) _cell_angle_gamma 86.653(17) _cell_formula_units_Z 2 _cell_length_a 5.1813(11) _cell_length_b 9.2173(18) _cell_length_c 10.6278(17) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 16.52 _cell_measurement_theta_min 8.33 _cell_volume 489.18(17) _computing_cell_refinement 'CAD-4 Software' _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989)' _computing_data_reduction 'HELENA (Spek, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material SHELXL97 _computing_structure_refinement SHELXL97 _computing_structure_solution 'SHELXS97 (Sheldrick, 1997b)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full .990 _diffrn_measured_fraction_theta_max .990 _diffrn_measurement_device_type 'Enraf-Nonius CAD-4' _diffrn_measurement_method 'profile data from \w-2\q scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .057 _diffrn_reflns_av_sigmaI/netI .018 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 3023 _diffrn_reflns_theta_full 27.47 _diffrn_reflns_theta_max 27.47 _diffrn_reflns_theta_min 3.01 _diffrn_standards_decay_% 1 _diffrn_standards_interval_time 180 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .133 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.454 _exptl_crystal_density_method 'not measured' _exptl_crystal_description irregular _exptl_crystal_F_000 228 _exptl_crystal_size_max .39 _exptl_crystal_size_mid .24 _exptl_crystal_size_min .24 _refine_diff_density_max .197 _refine_diff_density_min -.187 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.093 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 261 _refine_ls_number_reflns 3004 _refine_ls_number_restraints 3 _refine_ls_restrained_S_all 1.092 _refine_ls_R_factor_all .049 _refine_ls_R_factor_gt .034 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0451P)^2^+0.1464P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .094 _reflns_number_gt 2635 _reflns_number_total 3004 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file ln1087.cif _[local]_cod_data_source_block I _cod_original_cell_volume 489.18(16) _cod_database_code 2010543 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_type_symbol O1A .7748(3) .7173(2) .51470(17) .0326(4) Uani d . 1 O O2A .3856(3) .65527(19) .48602(17) .0305(4) Uani d . 1 O N1A -.0683(5) .7171(3) 1.2222(2) .0426(6) Uani d . 1 N H1A1 .0683 .7663 1.1857 .051 Uiso calc R 1 H H1A2 -.1227 .7116 1.3058 .051 Uiso calc R 1 H N2A -.3999(5) .5710(3) 1.2081(2) .0432(6) Uani d . 1 N H2A1 -.4500 .5638 1.2918 .052 Uiso calc R 1 H H2A2 -.4832 .5270 1.1617 .052 Uiso calc R 1 H N3A -.1112(5) .6584(3) 1.0217(2) .0360(5) Uani d . 1 N H3A -.1898 .6092 .9767 .043 Uiso calc R 1 H N4A .1506(4) .9178(2) .55354(18) .0262(4) Uani d . 1 N H4A1 .0595 .9892 .6029 .039 Uiso calc R 1 H H4A2 .0494 .8415 .5618 .039 Uiso calc R 1 H H4A3 .1955 .9480 .4706 .039 Uiso calc R 1 H C1A -.1937(5) .6504(3) 1.1505(2) .0327(5) Uani d . 1 C C2A .1070(5) .7471(3) .9538(2) .0316(5) Uani d . 1 C H2A3 .2713 .7098 .9737 0..038 Uiso calc R 1 H H2A4 .0709 .8459 .9845 .038 Uiso calc R 1 H C3A .1435(5) .7479(3) .8073(2) .0315(5) Uani d . 1 C H3A1 .2095 .6526 .7736 .038 Uiso calc R 1 H H3A2 -.0269 .7708 .7874 .038 Uiso calc R 1 H C4A .3413(5) .8604(3) .7439(2) .0282(5) Uani d . 1 C H4A4 .5092 .8361 .7659 .034 Uiso calc R 1 H H4A5 .2744 .9541 .7810 .034 Uiso calc R 1 H C5A .3971(4) .8754(2) .5959(2) .0235(4) Uani d . 1 C H5A .5222 .9530 .5672 .028 Uiso calc R 1 H C6A .5280(4) .7366(2) .52628(19) .0234(4) Uani d . 1 C O2B .8257(3) .15423(18) .68154(15) .0280(4) Uani d . 1 O O1B .4325(3) .2384(2) .65343(18) .0364(4) Uani d . 1 O N2B 1.0601(5) .2258(3) -.0692(2) .0401(5) Uani d . 1 N H2B1 1.1565 .2756 -.0337 .048 Uiso calc R 1 H H2B2 1.0938 .2228 -.1527 .048 Uiso calc R 1 H N1B .7157(5) .0756(3) -.0507(2) .0412(5) Uani d . 1 N H1B1 .7518 .0717 -.1343 .049 Uiso calc R 1 H H1B2 .5855 .0287 -.0031 .049 Uiso calc R 1 H N3B .8073(4) .1580(3) .13288(18) .0342(5) Uani d . 1 N H3B .6741 .1111 .1780 .041 Uiso calc R 1 H N4B 1.0017(4) .4356(2) .62012(18) .0264(4) Uani d . 1 N H4B1 1.0752 .5119 .5734 .040 Uiso calc R 1 H H4B2 1.1297 .3697 .6276 .040 Uiso calc R 1 H H4B3 .9103 .4642 .6990 .040 Uiso calc R 1 H C1B .8606(5) .1541(3) .0044(2) .0312(5) Uani d . 1 C C2B .9606(5) .2370(3) .2026(2) .0329(5) Uani d . 1 C H2B3 .9859 .3346 .1658 .039 Uiso calc R 1 H H2B4 1.1356 .1884 .1930 .039 Uiso calc R 1 H C3B .8149(5) .2443(3) .3456(2) .0321(5) Uani d . 1 C H3B1 .7846 .1467 .3817 .039 Uiso calc R 1 H H3B2 .6423 .2957 .3553 .039 Uiso calc R 1 H C4B .9801(5) .3228(3) .4194(2) .0299(5) Uani d . 1 C H4B4 1.1293 .2587 .4290 .036 Uiso calc R 1 H H4B5 1.0526 .4076 .3686 .036 Uiso calc R 1 H C5B .8170(4) .3704(2) .5536(2) .0233(4) Uani d . 1 C H5B .6805 .4447 .5431 .028 Uiso calc R 1 H C6B .6787(4) .2441(2) .63743(19) .0224(4) Uani d . 1 C F1 .4016(4) .4155(2) 1.0185(2) .0615(5) Uani d . 1 F H1 .508(11) .453(6) .931(5) .092 Uiso d . 1 H F2 .3956(4) 1.0056(2) .31635(16) .0576(5) Uani d . 1 F H2 .360(10) .944(5) .242(5) .086 Uiso d . 1 H F3 .6689(4) .5215(2) .84223(17) .0548(5) Uani d . 1 F F4 .3551(5) .9060(3) .13452(18) .0697(7) Uani d . 1 F loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1A .0207(8) .0343(9) .0412(9) -.0009(7) -.0045(7) -.0040(7) O2A .0269(9) .0285(9) .0349(8) -.0039(7) -.0043(7) -.0068(6) N1A .0429(13) .0567(15) .0238(10) -.0128(12) .0016(9) -.0015(10) N2A .0427(14) .0509(14) .0307(10) -.0130(11) .0024(9) .0004(10) N3A .0358(12) .0455(13) .0254(10) -.0097(10) -.0036(9) -.0035(9) N4A .0273(10) .0228(9) .0269(9) .0013(7) -.0045(7) -.0012(7) C1A .0337(13) .0347(13) .0261(11) .0026(10) -.0021(10) -.0012(9) C2A .0325(13) .0373(14) .0221(10) -.0015(10) -.0020(9) -.0023(9) C3A .0314(12) .0405(14) .0216(10) -.0078(11) -.0039(9) -.0004(9) C4A .0283(12) .0330(13) .0235(10) -.0037(10) -.0055(9) -.0072(9) C5A .0211(10) .0226(11) .0255(10) -.0032(8) -.0028(8) -.0015(8) C6A .0224(11) .0236(11) .0215(9) -.0030(8) -.0009(8) .0022(8) O2B .0276(8) .0270(8) .0277(8) .0006(7) -.0046(6) .0031(6) O1B .0215(9) .0409(10) .0452(9) -.0070(7) -.0058(7) .0086(8) N2B .0475(14) .0487(14) .0206(9) -.0110(11) -.0008(9) .0010(9) N1B .0500(15) .0492(14) .0264(10) -.0081(11) -.0117(10) -.0036(9) N3B .0354(12) .0459(13) .0210(9) -.0129(10) -.0046(8) -.0004(8) N4B .0268(10) .0240(9) .0274(9) -.0067(8) -.0038(8) -.0024(7) C1B .0357(14) .0327(13) .0236(11) .0029(10) -.0056(10) -.0023(9) C2B .0324(13) .0420(14) .0237(11) -.0086(11) -.0047(9) -.0013(10) C3B .0324(12) .0426(14) .0218(11) -.0126(11) -.0055(9) -.0022(9) C4B .0274(11) .0374(13) .0231(10) -.0140(10) -.0011(9) .0010(9) C5B .0221(11) .0230(11) .0249(10) -.0034(8) -.0059(8) .0009(8) C6B .0210(11) .0259(11) .0186(9) -.0049(8) -.0009(8) -.0026(8) F1 .0600(13) .0680(13) .0501(10) -.0285(11) .0023(9) .0019(9) F2 .0731(14) .0677(12) .0318(8) -.0337(10) -.0072(8) .0020(8) F3 .0528(11) .0612(12) .0410(8) -.0156(9) .0092(8) -.0115(8) F4 .0895(17) .0802(15) .0409(9) -.0427(13) -.0103(10) -.0071(9) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F .0171 .0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .0060 '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_publ_flag C1A N1A H1A1 120.0 ? C1A N1A H1A2 120.0 ? H1A1 N1A H1A2 120.0 ? C1A N2A H2A1 120.0 ? C1A N2A H2A2 120.0 ? H2A1 N2A H2A2 120.0 ? C1A N3A C2A 122.4(2) ? C1A N3A H3A 118.8 ? C2A N3A H3A 118.8 ? C5A N4A H4A1 109.5 ? C5A N4A H4A2 109.5 ? H4A1 N4A H4A2 109.5 ? C5A N4A H4A3 109.5 ? H4A1 N4A H4A3 109.5 ? H4A2 N4A H4A3 109.5 ? N1A C1A N3A 120.4(2) ? N1A C1A N2A 119.5(2) ? N3A C1A N2A 120.1(2) ? N3A C2A C3A 111.6(2) ? N3A C2A H2A3 109.3 ? C3A C2A H2A3 109.3 ? N3A C2A H2A4 109.3 ? C3A C2A H2A4 109.3 ? H2A3 C2A H2A4 108.0 ? C4A C3A C2A 109.1(2) ? C4A C3A H3A1 109.9 ? C2A C3A H3A1 109.9 ? C4A C3A H3A2 109.9 ? C2A C3A H3A2 109.9 ? H3A1 C3A H3A2 108.3 ? C3A C4A C5A 115.39(18) ? C3A C4A H4A4 108.4 ? C5A C4A H4A4 108.4 ? C3A C4A H4A5 108.4 ? C5A C4A H4A5 108.4 ? H4A4 C4A H4A5 107.5 ? N4A C5A C4A 112.03(18) ? N4A C5A C6A 109.07(18) ? C4A C5A C6A 112.78(19) ? N4A C5A H5A 107.6 ? C4A C5A H5A 107.6 ? C6A C5A H5A 107.6 ? O2A C6A O1A 126.1(2) yes O2A C6A C5A 118.5(2) ? O1A C6A C5A 115.5(2) ? C1B N2B H2B1 120.0 ? C1B N2B H2B2 120.0 ? H2B1 N2B H2B2 120.0 ? C1B N1B H1B1 120.0 ? C1B N1B H1B2 120.0 ? H1B1 N1B H1B2 120.0 ? C1B N3B C2B 123.9(2) ? C1B N3B H3B 118.1 ? C2B N3B H3B 118.1 ? C5B N4B H4B1 109.5 ? C5B N4B H4B2 109.5 ? H4B1 N4B H4B2 109.5 ? C5B N4B H4B3 109.5 ? H4B1 N4B H4B3 109.5 ? H4B2 N4B H4B3 109.5 ? N2B C1B N3B 120.5(2) ? N2B C1B N1B 119.7(2) ? N3B C1B N1B 119.8(3) ? N3B C2B C3B 110.09(19) ? N3B C2B H2B3 109.6 ? C3B C2B H2B3 109.6 ? N3B C2B H2B4 109.6 ? C3B C2B H2B4 109.6 ? H2B3 C2B H2B4 108.2 ? C2B C3B C4B 110.06(19) ? C2B C3B H3B1 109.6 ? C4B C3B H3B1 109.6 ? C2B C3B H3B2 109.6 ? C4B C3B H3B2 109.6 ? H3B1 C3B H3B2 108.2 ? C5B C4B C3B 112.65(19) ? C5B C4B H4B4 109.1 ? C3B C4B H4B4 109.1 ? C5B C4B H4B5 109.1 ? C3B C4B H4B5 109.1 ? H4B4 C4B H4B5 107.8 ? N4B C5B C4B 107.97(18) ? N4B C5B C6B 109.59(17) ? C4B C5B C6B 112.56(18) ? N4B C5B H5B 108.9 ? C4B C5B H5B 108.9 ? C6B C5B H5B 108.9 ? O1B C6B O2B 125.9(2) yes O1B C6B C5B 117.4(2) ? O2B C6B C5B 116.63(19) ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1A C6A . 1.255(3) yes O2A C6A . 1.242(3) yes N1A C1A . 1.311(4) ? N1A H1A1 . .8600 ? N1A H1A2 . .8600 ? N2A C1A . 1.331(4) ? N2A H2A1 . .8600 ? N2A H2A2 . .8600 ? N3A C1A . 1.325(3) ? N3A C2A . 1.452(3) ? N3A H3A . .8600 ? N4A C5A . 1.488(3) ? N4A H4A1 . .8900 ? N4A H4A2 . .8900 ? N4A H4A3 . .8900 ? C2A C3A . 1.519(3) ? C2A H2A3 . .9700 ? C2A H2A4 . .9700 ? C3A C4A . 1.515(3) ? C3A H3A1 . .9700 ? C3A H3A2 . .9700 ? C4A C5A . 1.526(3) ? C4A H4A4 . .9700 ? C4A H4A5 . .9700 ? C5A C6A . 1.533(3) ? C5A H5A . .9800 ? O2B C6B . 1.252(3) yes O1B C6B . 1.246(3) yes N2B C1B . 1.319(4) ? N2B H2B1 .. .8600 ? N2B H2B2 . .8600 ? N1B C1B . 1.324(4) ? N1B H1B1 . .8600 ? N1B H1B2 . .8600 ? N3B C1B . 1.322(3) ? N3B C2B . 1.457(3) ? N3B H3B . .8600 ? N4B C5B . 1.492(3) ? N4B H4B1 . .8900 ? N4B H4B2 . .8900 ? N4B H4B3 . .8900 ? C2B C3B . 1.513(3) ? C2B H2B3 . .9700 ? C2B H2B4 . .9700 ? C3B C4B . 1.527(3) ? C3B H3B1 . .9700 ? C3B H3B2 . .9700 ? C4B C5B . 1.523(3) ? C4B H4B4 . .9700 ? C4B H4B5 . .9700 ? C5B C6B . 1.533(3) ? C5B H5B . .9800 ? F1 H1 . 1.01(6) ? F2 H2 . 1.04(6) ? F3 H1 . 1.26(6) ? F4 H2 . 1.22(5) ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA F1 H1 F3 . 1.01(6) 1.26(6) 2.248(3) 163(5) F2 H2 F4 . 1.04(6) 1.22(5) 2.233(2) 161(5) N1A H1A1 F4 1_556 .86 1.98 2.825(3) 168 N1A H1A2 O1A 1_456 .86 2.15 3.002(3) 173 N2A H2A1 O2A 1_456 .86 2.20 2.987(3) 153 N2A H2A2 F1 1_455 .86 2.10 2.939(3) 167 N3A H3A F3 1_455 .86 1.98 2.829(3) 168 N4A H4A1 O2B 1_465 .89 1.96 2.835(3) 168 N4A H4A3 F2 . .89 1.78 2.632(3) 160 N4A H4A2 O1A 1_455 .89 2.05 2.876(3) 155 N2B H2B1 F1 1_654 .86 2.05 2.897(3) 169 N2B H2B2 O1B 1_654 .86 2.34 3.078(3) 144 N2B H2B2 O2B 1_554 .86 2.62 3.290(3) 135 N1B H1B1 O2B 1_554 .86 2.02 2.828(3) 156 N1B H1B2 F4 1_545 .86 1.99 2.831(3) 165 N3B H3B F2 1_545 .86 2.04 2.883(3) 168 N4B H4B1 O2A 1_655 .89 2.14 2.979(3) 157 N4B H4B1 O1A . .89 2.54 3.080(3) 120 N4B H4B3 F3 . .89 1.78 2.652(3) 168 N4B H4B2 O1B 1_655 .89 2.00 2.882(3) 174 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 _geom_torsion_publ_flag C2A N3A C1A N1A -4.0(4) n C2A N3A C1A N2A 177.9(2) n C1A N3A C2A C3A -174.6(3) n N3A C2A C3A C4A 170.8(2) n C2A C3A C4A C5A -179.4(2) n C3A C4A C5A N4A 60.1(3) n C3A C4A C5A C6A -63.4(3) ? N4A C5A C6A O2A -23.9(3) n C4A C5A C6A O2A 101.2(2) ? N4A C5A C6A O1A 155.50(18) n C4A C5A C6A O1A -79.3(2) ? C2B N3B C1B N2B -1.0(4) n C2B N3B C1B N1B 177.9(2) n C1B N3B C2B C3B 168.6(3) n N3B C2B C3B C4B 178.2(2) n C2B C3B C4B C5B 164.4(2) n C3B C4B C5B N4B 175.9(2) n C3B C4B C5B C6B 54.9(3) no N4B C5B C6B O1B 134.1(2) n C4B C5B C6B O1B -105.7(2) no N4B C5B C6B O2B -47.2(2) n C4B C5B C6B O2B 72.9(2) no