#------------------------------------------------------------------------------ #$Date: 2014-10-25 18:23:10 +0100 (Sat, 25 Oct 2014) $ #$Revision: 125873 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/51/2105170.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_2105170 loop_ _publ_author_name 'Tutughamiarso, Maya' 'Egert, Ernst' _publ_section_title ; Cocrystals of 5-fluorocytosine. II. Coformers with variable hydrogen-bonding sites ; _journal_coeditor_code GP5053 _journal_issue 4 _journal_name_full 'Acta Crystallographica Section B' _journal_page_first 444 _journal_page_last 452 _journal_volume 68 _journal_year 2012 _chemical_formula_moiety 'C4 H4 F N3 O, C5 H7 N3 O, H2 O' _chemical_formula_sum 'C9 H13 F N6 O3' _chemical_formula_weight 272.25 _chemical_name_systematic ; ? ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 97.103(12) _cell_angle_beta 93.662(13) _cell_angle_gamma 95.766(13) _cell_formula_units_Z 2 _cell_length_a 5.1193(8) _cell_length_b 9.3392(15) _cell_length_c 12.4862(19) _cell_measurement_reflns_used 2601 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 25.7 _cell_measurement_theta_min 4.02 _cell_volume 587.63(16) _computing_cell_refinement 'X-Area (Stoe & Cie, 2001)' _computing_data_collection 'X-Area (Stoe & Cie, 2001)' _computing_data_reduction 'X-Area (Stoe & Cie, 2001)' _computing_molecular_graphics 'Mercury (Macrae et al., 2008) and XP (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _diffrn_ambient_temperature 173(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'STOE IPDS II two-circle-diffractometer' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1813 _diffrn_reflns_av_sigmaI/netI 0.1350 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 8436 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.03 _diffrn_reflns_theta_min 3.72 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.129 _exptl_absorpt_correction_type none _exptl_crystal_density_diffrn 1.539 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 284 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.206 _refine_diff_density_min -0.299 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.783 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 197 _refine_ls_number_reflns 2070 _refine_ls_number_restraints 7 _refine_ls_restrained_S_all 0.784 _refine_ls_R_factor_all 0.0975 _refine_ls_R_factor_gt 0.0500 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0443P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1080 _refine_ls_wR_factor_ref 0.1219 _reflns_number_gt 1124 _reflns_number_total 2070 _reflns_threshold_expression I>2sigma(I) _iucr_refine_instructions_details ; TITL mt22-37 in P-1 CELL 0.71073 5.1193 9.3392 12.4862 97.103 93.662 95.766 ZERR 2.00 0.0008 0.0015 0.0019 0.012 0.013 0.013 LATT 1 SFAC C H F N O UNIT 18 26 2 12 6 REM farbloser Block SIZE 0.2 0.4 0.4 ACTA 50 L.S. 10 CONF BOND $H FMAP 2 PLAN 10 SHEL 999 .84 DFIX 0.88 0.02 O1W H1W O1W H2W DFIX 1.44 0.04 H1W H2W DFIX 0.88 0.02 N21 H21A N21 H21B DFIX 0.88 0.02 N41' H41A N41' H41B TEMP -100 EQIV_$1 -x+1, -y, -z+1 EQIV_$2 -x+1, -y+1, -z+2 EQIV_$3 -x, -y, -z+1 HTAB N3 N3' HTAB N21 O21'_$1 HTAB N21 O21' HTAB N1' O1W_$1 HTAB N41' O41 HTAB N41' O41_$2 HTAB O1W O21'_$3 HTAB O1W N1 WGHT 0.044300 FVAR 0.52109 N1 4 -0.052772 -0.047799 0.720860 11.00000 0.02355 0.02001 = 0.02020 0.00062 0.00184 -0.00398 C2 1 0.147356 0.043499 0.699119 11.00000 0.02164 0.01902 = 0.01831 -0.00280 -0.00071 0.00146 N3 4 0.245928 0.163207 0.768937 11.00000 0.02112 0.01966 = 0.01810 -0.00193 0.00321 -0.00310 H3 2 0.377215 0.220839 0.752662 11.00000 -1.20000 C4 1 0.144491 0.200586 0.867687 11.00000 0.02179 0.02216 = 0.01800 -0.00224 0.00074 0.00340 C5 1 -0.069981 0.105279 0.891103 11.00000 0.02888 0.02313 = 0.01768 0.00074 0.00642 -0.00193 AFIX 43 H5 2 -0.152483 0.124173 0.956637 11.00000 -1.20000 AFIX 0 C6 1 -0.158068 -0.014690 0.818485 11.00000 0.02518 0.02098 = 0.02154 0.00325 0.00130 0.00201 N21 4 0.263780 0.021171 0.606163 11.00000 0.03154 0.02817 = 0.02482 -0.01062 0.00665 -0.00694 H21A 2 0.196335 -0.058013 0.566491 11.00000 -1.20000 H21B 2 0.402480 0.079259 0.587364 11.00000 -1.20000 O41 5 0.247849 0.311902 0.926852 11.00000 0.03246 0.02406 = 0.01831 -0.00875 0.00759 -0.00552 C61 1 -0.380391 -0.120812 0.840541 11.00000 0.03397 0.02661 = 0.02834 0.00612 0.00592 -0.00161 AFIX 137 H61A 2 -0.313405 -0.212835 0.852062 11.00000 -1.50000 H61B 2 -0.512196 -0.137238 0.778587 11.00000 -1.50000 H61C 2 -0.461331 -0.081937 0.905434 11.00000 -1.50000 AFIX 0 N1' 4 1.040498 0.398671 0.603019 11.00000 0.02489 0.02571 = 0.01597 -0.00077 0.00662 0.00296 H1' 2 1.104888 0.369160 0.539168 11.00000 -1.20000 C2' 1 0.809882 0.320929 0.623021 11.00000 0.01782 0.02114 = 0.01958 0.00049 0.00270 0.00044 N3' 4 0.699848 0.350826 0.717792 11.00000 0.01927 0.02038 = 0.01761 -0.00558 0.00201 0.00038 C4' 1 0.816973 0.459287 0.792129 11.00000 0.01757 0.01799 = 0.01867 -0.00052 0.00222 0.00045 C5' 1 1.052853 0.538959 0.770322 11.00000 0.02250 0.01922 = 0.02045 -0.00498 -0.00209 -0.00235 C6' 1 1.162225 0.509107 0.676796 11.00000 0.02262 0.02223 = 0.02262 0.00299 0.00166 -0.00407 AFIX 43 H6' 2 1.320165 0.563240 0.662134 11.00000 -1.20000 AFIX 0 O21' 5 0.704411 0.220863 0.551113 11.00000 0.02809 0.02966 = 0.01759 -0.00996 0.00193 -0.00132 N41' 4 0.707138 0.487531 0.884186 11.00000 0.02839 0.02843 = 0.01980 -0.01216 0.00844 -0.00745 H41A 2 0.560884 0.431098 0.898846 11.00000 -1.20000 H41B 2 0.786075 0.556956 0.934086 11.00000 -1.20000 F51' 3 1.162847 0.647242 0.848188 11.00000 0.03100 0.03193 = 0.03123 -0.01240 0.00357 -0.01340 O1W 5 -0.299142 -0.303196 0.581843 11.00000 0.02753 0.03086 = 0.02149 -0.00229 0.00127 0.00103 H1W 2 -0.437122 -0.275950 0.545172 11.00000 -1.20000 H2W 2 -0.204481 -0.229546 0.621414 11.00000 -1.20000 HKLF 4 REM mt22-37 in P-1 REM R1 = 0.0535 for 1127 Fo > 4sig(Fo) and 0.1005 for all 2070 data REM 197 parameters refined using 7 restraints END ; _[local]_cod_data_source_file gp5053.cif _[local]_cod_data_source_block IVb _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26. Automatic conversion script Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius ; _cod_database_code 2105170 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_type_symbol _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_symmetry_multiplicity N N1 -0.0530(5) -0.0477(3) 0.7209(2) 0.0227(6) Uani d . 1 1 C C2 0.1476(6) 0.0437(3) 0.6993(2) 0.0209(7) Uani d . 1 1 N N3 0.2458(5) 0.1631(3) 0.76886(19) 0.0210(6) Uani d . 1 1 H H3 0.376(7) 0.221(3) 0.753(3) 0.025 Uiso d . 1 1 C C4 0.1448(6) 0.2007(3) 0.8679(2) 0.0214(7) Uani d . 1 1 C C5 -0.0698(6) 0.1053(3) 0.8911(2) 0.0246(7) Uani d . 1 1 H H5 -0.1526 0.1242 0.9566 0.030 Uiso calc R 1 1 C C6 -0.1578(6) -0.0146(3) 0.8186(2) 0.0234(7) Uani d . 1 1 N N21 0.2636(6) 0.0212(3) 0.6061(2) 0.0303(7) Uani d D 1 1 H H21A 0.198(7) -0.059(3) 0.565(2) 0.036 Uiso d D 1 1 H H21B 0.402(5) 0.080(3) 0.588(3) 0.036 Uiso d D 1 1 O O41 0.2478(4) 0.3120(2) 0.92671(16) 0.0271(6) Uani d . 1 1 C C61 -0.3800(7) -0.1210(3) 0.8406(3) 0.0306(8) Uani d . 1 1 H H61A -0.3126 -0.2130 0.8522 0.046 Uiso calc R 1 1 H H61B -0.5117 -0.1376 0.7786 0.046 Uiso calc R 1 1 H H61C -0.4612 -0.0823 0.9055 0.046 Uiso calc R 1 1 N N1' 1.0402(5) 0.3988(3) 0.6031(2) 0.0229(6) Uani d . 1 1 H H1' 1.102(7) 0.368(3) 0.541(3) 0.027 Uiso d . 1 1 C C2' 0.8096(6) 0.3209(3) 0.6229(2) 0.0205(7) Uani d . 1 1 N N3' 0.6997(5) 0.3510(2) 0.71785(19) 0.0206(6) Uani d . 1 1 C C4' 0.8169(6) 0.4591(3) 0.7921(2) 0.0190(7) Uani d . 1 1 C C5' 1.0530(6) 0.5391(3) 0.7704(2) 0.0224(7) Uani d . 1 1 C C6' 1.1624(6) 0.5089(3) 0.6769(2) 0.0237(7) Uani d . 1 1 H H6' 1.3208 0.5626 0.6623 0.028 Uiso calc R 1 1 O O21' 0.7045(4) 0.2209(2) 0.55116(16) 0.0272(5) Uani d . 1 1 N N41' 0.7071(6) 0.4875(3) 0.8843(2) 0.0280(7) Uani d D 1 1 H H41A 0.558(5) 0.429(3) 0.897(3) 0.034 Uiso d D 1 1 H H41B 0.786(6) 0.557(3) 0.935(2) 0.034 Uiso d D 1 1 F F51' 1.1630(4) 0.64720(19) 0.84809(15) 0.0347(5) Uani d . 1 1 O O1W -0.2989(5) -0.3032(2) 0.58184(18) 0.0283(5) Uani d D 1 1 H H1W -0.439(5) -0.276(3) 0.545(2) 0.034 Uiso d D 1 1 H H2W -0.207(6) -0.228(3) 0.623(2) 0.034 Uiso d D 1 1 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 N1 0.0247(16) 0.0217(13) 0.0204(14) -0.0022(11) 0.0023(11) 0.0018(10) C2 0.0226(18) 0.0195(16) 0.0192(16) 0.0025(13) -0.0007(13) -0.0017(12) N3 0.0224(16) 0.0208(14) 0.0186(14) -0.0019(11) 0.0035(11) -0.0003(11) C4 0.0218(18) 0.0232(16) 0.0186(15) 0.0045(13) 0.0010(13) -0.0014(13) C5 0.0301(19) 0.0250(16) 0.0183(15) -0.0010(13) 0.0067(13) 0.0020(12) C6 0.026(2) 0.0223(16) 0.0218(16) 0.0025(13) 0.0016(13) 0.0036(12) N21 0.0322(18) 0.0291(15) 0.0252(15) -0.0056(12) 0.0073(12) -0.0092(11) O41 0.0339(14) 0.0249(12) 0.0191(11) -0.0043(10) 0.0082(10) -0.0075(9) C61 0.035(2) 0.0289(18) 0.0289(17) -0.0003(15) 0.0069(15) 0.0071(13) N1' 0.0259(16) 0.0273(14) 0.0159(13) 0.0046(12) 0.0065(11) 0.0005(11) C2' 0.0187(17) 0.0222(15) 0.0203(16) 0.0017(12) 0.0029(13) 0.0012(12) N3' 0.0206(15) 0.0210(13) 0.0184(13) 0.0016(11) 0.0025(11) -0.0048(10) C4' 0.0186(18) 0.0189(15) 0.0194(16) 0.0024(13) 0.0019(12) 0.0011(12) C5' 0.0229(18) 0.0197(16) 0.0217(16) -0.0020(13) -0.0012(13) -0.0039(12) C6' 0.0239(19) 0.0229(16) 0.0237(17) -0.0032(13) 0.0024(14) 0.0047(13) O21' 0.0292(14) 0.0305(12) 0.0180(11) -0.0006(10) 0.0024(9) -0.0088(9) N41' 0.0300(17) 0.0293(15) 0.0199(13) -0.0063(12) 0.0090(12) -0.0113(11) F51' 0.0331(12) 0.0328(11) 0.0314(10) -0.0126(8) 0.0044(8) -0.0108(8) O1W 0.0293(14) 0.0324(13) 0.0217(11) 0.0021(10) 0.0022(10) -0.0012(9) 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' 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' O O 0.0106 0.0060 '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 C2 N1 C6 116.2(2) N1 C2 N21 120.9(3) N1 C2 N3 122.5(3) N21 C2 N3 116.6(3) C2 N3 C4 123.0(3) C2 N3 H3 120(2) C4 N3 H3 117(2) O41 C4 N3 118.6(3) O41 C4 C5 126.5(3) N3 C4 C5 114.9(3) C6 C5 C4 119.5(3) C6 C5 H5 120.2 C4 C5 H5 120.2 C5 C6 N1 123.8(3) C5 C6 C61 121.6(3) N1 C6 C61 114.6(3) C2 N21 H21A 113(2) C2 N21 H21B 124(2) H21A N21 H21B 123(3) C6 C61 H61A 109.5 C6 C61 H61B 109.5 H61A C61 H61B 109.5 C6 C61 H61C 109.5 H61A C61 H61C 109.5 H61B C61 H61C 109.5 C6' N1' C2' 121.5(3) C6' N1' H1' 125(2) C2' N1' H1' 114(2) O21' C2' N3' 121.1(3) O21' C2' N1' 118.6(3) N3' C2' N1' 120.3(3) C4' N3' C2' 119.3(3) N41' C4' N3' 118.6(3) N41' C4' C5' 121.5(3) N3' C4' C5' 119.8(3) C6' C5' F51' 121.7(3) C6' C5' C4' 120.9(3) F51' C5' C4' 117.4(3) C5' C6' N1' 118.1(3) C5' C6' H6' 120.9 N1' C6' H6' 120.9 C4' N41' H41A 119(2) C4' N41' H41B 119(2) H41A N41' H41B 122(3) H1W O1W H2W 112(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance N1 C2 1.331(4) N1 C6 1.377(4) C2 N21 1.343(4) C2 N3 1.358(4) N3 C4 1.390(4) N3 H3 0.87(3) C4 O41 1.244(3) C4 C5 1.411(4) C5 C6 1.368(4) C5 H5 0.9500 C6 C61 1.496(4) N21 H21A 0.871(18) N21 H21B 0.910(18) C61 H61A 0.9800 C61 H61B 0.9800 C61 H61C 0.9800 N1' C6' 1.363(4) N1' C2' 1.376(4) N1' H1' 0.88(3) C2' O21' 1.262(3) C2' N3' 1.355(4) N3' C4' 1.347(4) C4' N41' 1.323(4) C4' C5' 1.415(4) C5' C6' 1.338(4) C5' F51' 1.361(3) C6' H6' 0.9500 N41' H41A 0.924(18) N41' H41B 0.893(18) O1W H1W 0.898(18) O1W H2W 0.891(18) 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 N3 H3 N3' . 0.87(3) 2.06(3) 2.921(3) 177(3) N21 H21A O21' 2_656 0.871(18) 2.09(3) 2.831(3) 143(3) N21 H21B O21' . 0.910(18) 2.043(19) 2.952(4) 177(3) N1' H1' O1W 2_656 0.88(3) 1.96(3) 2.829(3) 170(3) N41' H41A O41 . 0.924(18) 1.922(19) 2.845(4) 178(3) N41' H41B O41 2_667 0.893(18) 2.02(2) 2.807(3) 146(3) O1W H1W O21' 2_556 0.898(18) 1.913(19) 2.803(3) 171(3) O1W H2W N1 . 0.891(18) 2.013(19) 2.896(3) 171(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 C6 N1 C2 N21 -179.9(3) C6 N1 C2 N3 0.1(4) N1 C2 N3 C4 -0.4(5) N21 C2 N3 C4 179.6(3) C2 N3 C4 O41 179.8(3) C2 N3 C4 C5 -0.3(4) O41 C4 C5 C6 -178.8(3) N3 C4 C5 C6 1.2(4) C4 C5 C6 N1 -1.7(5) C4 C5 C6 C61 178.4(3) C2 N1 C6 C5 1.0(5) C2 N1 C6 C61 -179.1(3) C6' N1' C2' O21' 179.5(3) C6' N1' C2' N3' -0.9(5) O21' C2' N3' C4' -179.6(3) N1' C2' N3' C4' 0.8(4) C2' N3' C4' N41' 179.8(3) C2' N3' C4' C5' -0.3(4) N41' C4' C5' C6' 179.8(3) N3' C4' C5' C6' -0.1(5) N41' C4' C5' F51' -0.2(4) N3' C4' C5' F51' 179.9(3) F51' C5' C6' N1' 180.0(3) C4' C5' C6' N1' 0.0(5) C2' N1' C6' C5' 0.5(5) _journal_paper_doi 10.1107/S0108768112029977