#------------------------------------------------------------------------------ #$Date: 2013-08-29 16:37:19 +0100 (Thu, 29 Aug 2013) $ #$Revision: 88064 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/07/2200709.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_2200709 loop_ _publ_author_name 'Prabakaran, P.' 'Murugesan, S.' 'Muthiah, P. Thomas' 'Bocelli, G.' 'Righi, L.' _publ_section_title ; Intermolecular N--H···O hydrogen-bonding interactions in 5-fluorocytosinium salicylate ; _journal_issue 10 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o933 _journal_page_last o936 _journal_volume 57 _journal_year 2001 _chemical_formula_iupac 'C4 H5 F N3 O 1+, C7 H5 O3 1-' _chemical_formula_moiety 'C4 H5 F N3 O 1+, C7 H5 O3 1-' _chemical_formula_sum 'C11 H10 F N3 O4' _chemical_formula_weight 267.22 _chemical_name_common '5-fluorocytosinium salicylate' _chemical_name_systematic ; ? ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _cell_angle_alpha 90 _cell_angle_beta 101.540(15) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 13.509(5) _cell_length_b 10.519(3) _cell_length_c 8.099(2) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293 _cell_measurement_theta_max 25.0 _cell_measurement_theta_min 2.0 _cell_volume 1127.6(6) _computing_cell_refinement MolEN _computing_data_collection 'MolEN (Fair, 1990)' _computing_data_reduction MolEN _computing_molecular_graphics 'PLATON (Spek, 1997) and RPluto (Cambridge Structural Database, 2000)' _computing_publication_material 'PLATON (Spek, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXL97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 5.37 _diffrn_measured_fraction_theta_max 5.37 _diffrn_measurement_device_type 'Enraf Nonius CAD-4' _diffrn_measurement_method \w--2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents .0099 _diffrn_reflns_av_sigmaI/netI .0276 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -2 _diffrn_reflns_number 2289 _diffrn_reflns_reduction_process ; ? ; _diffrn_reflns_theta_full 69.95 _diffrn_reflns_theta_max 69.95 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 60 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 1.15 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.574 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_method 'Not Measured' _exptl_crystal_description needle _exptl_crystal_F_000 552 _exptl_crystal_size_max .26 _exptl_crystal_size_mid .23 _exptl_crystal_size_min .17 _refine_diff_density_max .193 _refine_diff_density_min -.160 _refine_ls_extinction_coef .0066(7) _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 192 _refine_ls_number_reflns 2141 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.019 _refine_ls_R_factor_all .0465 _refine_ls_R_factor_gt .0342 _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^)+(0.1407P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .1026 _reflns_number_gt 1631 _reflns_number_total 2141 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file ob6069.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/n' _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. '_refine_ls_weighting_scheme' value 'calc ' changed to 'calc' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2200709 loop_ _symmetry_equiv_pos_as_xyz x,y,z 1/2-x,1/2+y,1/2-z -x,-y,-z 1/2+x,1/2-y,1/2+z 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 O3 .0285(5) .0346(6) .0583(7) .0010(4) .0041(5) .0022(5) O4 .0320(6) .0436(7) .0718(8) .0019(5) .0009(5) .0129(6) O5 .0337(6) .0620(9) .0902(11) -.0051(6) .0047(6) .0059(8) C7 .0392(8) .0407(9) .0549(10) -.0022(7) .0149(7) -.0097(8) C8 .0559(11) .0513(11) .0715(12) -.0156(9) .0292(10) -.0126(9) C9 .0834(14) .0419(10) .0651(12) -.0037(10) .0386(11) .0017(9) C10 .0693(12) .0465(10) .0515(10) .0066(9) .0219(9) .0050(8) C11 .0464(9) .0414(9) .0455(9) .0048(7) .0126(7) -.0004(7) C12 .0375(8) .0319(8) .0443(8) .0006(6) .0115(6) -.0062(7) C13 .0299(7) .0318(8) .0455(8) .0024(6) .0037(6) -.0048(6) F1 .0470(5) .0464(6) .0488(5) -.0073(4) -.0010(4) -.0094(4) O2 .0286(5) .0458(7) .0619(7) -.0014(5) -.0081(5) -.0024(6) N1 .0289(6) .0370(7) .0555(8) .0057(5) .0026(6) .0045(6) N3 .0250(6) .0309(6) .0420(7) .0017(5) -.0008(5) .0000(5) N4 .0260(6) .0410(8) .0476(8) .0007(5) -.0032(5) -.0039(6) C2 .0259(7) .0372(8) .0446(8) .0009(6) .0005(6) .0067(7) C4 .0280(7) .0320(7) .0359(7) -.0017(5) .0012(5) .0052(6) C5 .0355(7) .0335(8) .0369(8) -.0042(6) .0020(6) .0008(6) C6 .0413(8) .0317(8) .0486(9) .0027(6) .0106(7) .0021(7) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy _atom_site_type_symbol O3 .07135(7) .47759(10) .79894(14) .0411(3) Uani 1.000 O O4 -.08899(8) .51316(11) .6807(2) .0505(4) Uani 1.000 O O5 -.22903(9) .36377(15) .7271(2) .0630(5) Uani 1.000 O C7 -.15615(12) .2994(2) .8345(2) .0442(5) Uani 1.000 C C8 -.1844(2) .1901(2) .9123(3) .0573(7) Uani 1.000 C C9 -.1133(2) .1213(2) 1.0227(3) .0602(7) Uani 1.000 C C10 -.0134(2) .1602(2) 1.0603(2) .0544(6) Uani 1.000 C C11 .01514(13) .2674(2) .9830(2) .0440(5) Uani 1.000 C C12 -.05457(11) .33791(14) .8671(2) .0374(5) Uani 1.000 C C13 -.02160(11) .45017(14) .7781(2) .0363(4) Uani 1.000 C F1 .48059(7) .43555(9) 1.14158(12) .0489(3) Uani 1.000 F O2 .20854(8) .16762(11) .7089(2) .0478(4) Uani 1.000 O N1 .24711(9) .34496(13) .8719(2) .0413(4) Uani 1.000 N N3 .37067(8) .19523(11) .8498(2) .0337(4) Uani 1.000 N N4 .53687(9) .22223(14) .9866(2) .0397(4) Uani 1.000 N C2 .27041(11) .23208(14) .8042(2) .0368(4) Uani 1.000 C C4 .44313(10) .26105(13) .9563(2) .0327(4) Uani 1.000 C C5 .41056(11) .37238(14) 1.0295(2) .0360(4) Uani 1.000 C C6 .31536(12) .41294(15) .9853(2) .0403(5) Uani 1.000 C H5 -.196(2) .435(3) .689(3) .102(9) Uiso 1.000 H H8 -.2514(2) .1638(2) .8894(3) .074(7) Uiso 1.000 H H9 -.1327(2) .0482(2) 1.0724(3) .067(6) Uiso 1.000 H H10 .0341(2) .1145(2) 1.1366(2) .068(6) Uiso 1.000 H H11 .08225(13) .2935(2) 1.0086(2) .051(5) Uiso 1.000 H H1 .17910 .38000 .84010 .084(7) Uiso 1.000 H H3 .39020 .12000 .80020 .051(5) Uiso 1.000 H H4A .5533(15) .146(2) .931(3) .065(6) Uiso 1.000 H H4B .5839(15) .2663(18) 1.059(2) .053(5) Uiso 1.000 H H6 .29551(12) .48731(15) 1.0317(2) .059(6) Uiso 1.000 H loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag F1 C5 . . 1.348(2) yes O3 C13 . . 1.266(2) yes O4 C13 . . 1.266(2) yes O5 C7 . . 1.357(2) yes O5 H5 . . .95(3) no O2 C2 . . 1.223(2) yes N1 C6 . . 1.366(2) yes N1 C2 . . 1.371(2) yes N3 C2 . . 1.386(2) yes N3 C4 . . 1.358(2) yes N4 C4 . . 1.306(2) yes N1 H1 . . .9755 no N3 H3 . . .9485 no N4 H4B . . .902(18) no N4 H4A . . .97(2) no C7 C12 . . 1.404(2) no C7 C8 . . 1.400(3) no C8 C9 . . 1.379(3) no C9 C10 . . 1.385(4) no C10 C11 . . 1.382(3) no C11 C12 . . 1.402(2) no C12 C13 . . 1.497(2) no C8 H8 . . .929(4) no C9 H9 . . .930(3) no C10 H10 . . .931(3) no C11 H11 . . .930(3) no C4 C5 . . 1.422(2) no C5 C6 . . 1.334(2) no C6 H6 . . .930(2) no loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O .0492 .0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0311 .0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F .0727 .0534 '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' C C .0181 .0091 '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 C7 O5 H5 105.8(16) no C2 N1 C6 122.98(13) yes C2 N3 C4 124.65(13) yes C6 N1 H1 116.94 no C2 N1 H1 120.08 no C2 N3 H3 117.41 no C4 N3 H3 117.92 no H4A N4 H4B 122.1(18) no C4 N4 H4A 118.4(13) no C4 N4 H4B 119.5(13) no O5 C7 C8 118.03(17) yes O5 C7 C12 122.20(17) yes C8 C7 C12 119.76(18) no C7 C8 C9 120.4(2) no C8 C9 C10 120.6(2) no C9 C10 C11 119.32(19) no C10 C11 C12 121.63(18) no C11 C12 C13 121.01(14) no C7 C12 C11 118.27(15) no C7 C12 C13 120.71(14) no O4 C13 C12 117.82(14) yes O3 C13 O4 122.28(14) yes O3 C13 C12 119.88(14) yes C9 C8 H8 119.8(3) no C7 C8 H8 119.8(3) no C10 C9 H9 119.7(3) no C8 C9 H9 119.6(3) no C9 C10 H10 120.4(3) no C11 C10 H10 120.3(3) no C12 C11 H11 119.2(2) no C10 C11 H11 119.2(2) no N1 C2 N3 115.22(13) yes O2 C2 N1 123.37(14) yes O2 C2 N3 121.41(14) yes N3 C4 N4 120.57(13) yes N3 C4 C5 116.17(13) yes N4 C4 C5 123.26(14) yes F1 C5 C4 116.93(13) yes F1 C5 C6 122.14(14) yes C4 C5 C6 120.91(14) no N1 C6 C5 119.85(15) yes N1 C6 H6 120.10(19) no C5 C6 H6 120.05(19) no 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 _geom_hbond_publ_flag N1 H1 O3 . .98 1.76 2.7151(19) 166 yes N3 H3 O3 2_546 .95 1.82 2.7719(19) 179 yes N4 H4A O4 2_546 .97(2) 1.78(2) 2.748(2) 175(2) yes N4 H4B F1 . .902(18) 2.437(19) 2.751(2) 100.7(15) yes N4 H4B O2 4_555 .902(18) 1.994(19) 2.880(2) 167.0(18) yes O5 H5 O4 . .95(3) 1.68(3) 2.544(2) 149(3) yes 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 C2 N1 C6 C5 2.7(2) no C6 N1 C2 O2 176.36(16) no C6 N1 C2 N3 -4.3(2) no C2 N3 C4 N4 -176.95(15) no C4 N3 C2 N1 1.5(2) no C4 N3 C2 O2 -179.18(16) no C2 N3 C4 C5 2.7(2) no C8 C7 C12 C13 176.56(17) no O5 C7 C8 C9 -179.9(2) no O5 C7 C12 C13 -2.5(3) no C8 C7 C12 C11 -2.5(3) no O5 C7 C12 C11 178.48(16) no C12 C7 C8 C9 1.0(3) no C7 C8 C9 C10 1.0(3) no C8 C9 C10 C11 -1.5(3) no C9 C10 C11 C12 -.1(3) no C10 C11 C12 C7 2.0(3) no C10 C11 C12 C13 -177.01(16) no C7 C12 C13 O3 -174.45(15) no C7 C12 C13 O4 4.1(2) no C11 C12 C13 O3 4.6(2) no C11 C12 C13 O4 -176.89(16) no N3 C4 C5 F1 176.98(13) no N4 C4 C5 C6 175.19(16) no N3 C4 C5 C6 -4.5(2) no N4 C4 C5 F1 -3.4(2) no C4 C5 C6 N1 1.9(2) no F1 C5 C6 N1 -179.58(14) no _cod_database_fobs_code 2200709