#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:01:59 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301802 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/51/2105156.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_2105156 loop_ _publ_author_name 'Tutughamiarso, Maya' 'Wagner, Guido' 'Egert, Ernst' _publ_section_title ; Cocrystals of 5-fluorocytosine. I. Coformers with fixed hydrogen-bonding sites ; _journal_coeditor_code GP5052 _journal_issue 4 _journal_name_full 'Acta Crystallographica Section B' _journal_page_first 431 _journal_page_last 443 _journal_paper_doi 10.1107/S010876811202561X _journal_volume 68 _journal_year 2012 _chemical_formula_moiety 'C4 H4 F N3 O, C4 H5 N3' _chemical_formula_sum 'C8 H9 F N6 O' _chemical_formula_weight 224.21 _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 105.371(18) _cell_angle_beta 101.944(16) _cell_angle_gamma 91.700(18) _cell_formula_units_Z 2 _cell_length_a 6.2414(12) _cell_length_b 7.2335(17) _cell_length_c 11.546(2) _cell_measurement_reflns_used 2478 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 25.73 _cell_measurement_theta_min 3.45 _cell_volume 489.76(18) _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 0.995 _diffrn_measured_fraction_theta_max 0.989 _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 0.1379 _diffrn_reflns_av_sigmaI/netI 0.0991 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 4298 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.61 _diffrn_reflns_theta_min 3.46 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.122 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.520 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 232 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.318 _refine_diff_density_min -0.379 _refine_ls_extinction_coef 0.058(18) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 0.947 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 161 _refine_ls_number_reflns 1834 _refine_ls_number_restraints 4 _refine_ls_restrained_S_all 0.946 _refine_ls_R_factor_all 0.0955 _refine_ls_R_factor_gt 0.0720 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1395P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1879 _refine_ls_wR_factor_ref 0.2098 _reflns_number_gt 1246 _reflns_number_total 1834 _reflns_threshold_expression I>2\s(I) _iucr_refine_instructions_details ; TITL mt24-7 in P-1 CELL 0.71073 6.2414 7.2335 11.546 105.371 101.944 91.700 ZERR 2.00 0.0012 0.0017 0.002 0.018 0.016 0.018 LATT 1 SFAC C H F N O UNIT 16 18 2 12 2 L.S. 10 BOND $H CONF FMAP 2 PLAN 10 ACTA 50 REM farbloser Block SIZE 0.1 0.1 0.4 TEMP -100 DFIX 0.88 0.02 N21 H21A N21 H21B DFIX 0.88 0.02 N41' H41A N41' H41B EQIV_$1 -x+2, -y+1, -z+1 EQIV_$2 -x+2, -y+1, -z+2 EQIV_$3 x , y , z+1 HTAB N21 O21'_$1 HTAB N21 O21' HTAB N1' N3 HTAB N41' N3'_$2 HTAB N41' N1_$3 WGHT 0.139500 EXTI 0.058210 FVAR 0.92723 N1 4 0.481529 0.261709 0.206795 11.00000 0.02894 0.03597 = 0.03321 0.01074 0.00956 0.00136 C2 1 0.552176 0.280886 0.328944 11.00000 0.03008 0.03238 = 0.03525 0.01051 0.01327 0.00717 N3 4 0.431072 0.222501 0.400594 11.00000 0.02467 0.04116 = 0.03256 0.01033 0.00907 0.00051 C4 1 0.226191 0.144598 0.345193 11.00000 0.02551 0.04326 = 0.03245 0.01007 0.00859 -0.00019 AFIX 43 H4 2 0.137399 0.104158 0.393147 11.00000 -1.20000 AFIX 0 C5 1 0.137237 0.120062 0.221056 11.00000 0.02592 0.04128 = 0.03630 0.00561 0.00440 -0.00567 AFIX 43 H5 2 -0.008536 0.064248 0.183011 11.00000 -1.20000 AFIX 0 C6 1 0.274212 0.182006 0.156158 11.00000 0.03080 0.03940 = 0.03048 0.00586 0.00359 -0.00205 AFIX 43 H6 2 0.218741 0.167452 0.070865 11.00000 -1.20000 AFIX 0 N21 4 0.757390 0.357424 0.384773 11.00000 0.02204 0.05334 = 0.03526 0.01537 0.00696 -0.00608 H21A 2 0.804176 0.391149 0.466725 11.00000 -1.20000 H21B 2 0.833831 0.412457 0.345100 11.00000 -1.20000 N1' 4 0.571844 0.273870 0.657754 11.00000 0.02427 0.03815 = 0.02468 0.00953 0.00135 -0.00291 H1' 2 0.537488 0.247730 0.576664 11.00000 -1.20000 C2' 1 0.782261 0.350015 0.720394 11.00000 0.02337 0.03254 = 0.03454 0.01183 0.00624 0.00110 N3' 4 0.839952 0.383205 0.845618 11.00000 0.02125 0.03620 = 0.03308 0.01236 0.00403 -0.00126 C4' 1 0.696131 0.329864 0.905638 11.00000 0.02662 0.02986 = 0.03212 0.01079 0.00780 0.00258 C5' 1 0.484824 0.242326 0.837996 11.00000 0.02461 0.04136 = 0.03301 0.01295 0.00995 -0.00183 C6' 1 0.422338 0.220328 0.716051 11.00000 0.02402 0.04288 = 0.03565 0.01073 0.00716 -0.00166 AFIX 43 H6' 2 0.277730 0.168800 0.671854 11.00000 -1.20000 AFIX 0 O21' 5 0.915260 0.389776 0.660243 11.00000 0.03001 0.05157 = 0.03803 0.01880 0.01057 -0.00312 N41' 4 0.752683 0.359879 1.027088 11.00000 0.02678 0.04694 = 0.03217 0.01298 0.00538 -0.00559 H41A 2 0.660669 0.320341 1.067932 11.00000 -1.20000 H41B 2 0.879237 0.427716 1.064124 11.00000 -1.20000 F51' 3 0.343159 0.187205 0.900499 11.00000 0.03036 0.06781 = 0.03732 0.01641 0.01138 -0.01215 HKLF 4 REM mt24-7 in P-1 REM R1 = 0.0720 for 1246 Fo > 4sig(Fo) and 0.0955 for all 1834 data REM 161 parameters refined using 4 restraints END ; _cod_data_source_file gp5052.cif _cod_data_source_block I _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_original_cell_volume 489.76(17) _cod_database_code 2105156 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 0.4815(4) 0.2617(4) 0.2068(2) 0.0321(6) Uani d . 1 1 C C2 0.5522(5) 0.2809(4) 0.3289(3) 0.0314(7) Uani d . 1 1 N N3 0.4311(4) 0.2225(4) 0.4006(2) 0.0324(6) Uani d . 1 1 C C4 0.2262(4) 0.1446(5) 0.3452(3) 0.0336(7) Uani d . 1 1 H H4 0.1374 0.1042 0.3931 0.040 Uiso calc R 1 1 C C5 0.1372(5) 0.1201(5) 0.2211(3) 0.0361(7) Uani d . 1 1 H H5 -0.0085 0.0642 0.1830 0.043 Uiso calc R 1 1 C C6 0.2742(5) 0.1820(5) 0.1562(3) 0.0349(7) Uani d . 1 1 H H6 0.2187 0.1675 0.0709 0.042 Uiso calc R 1 1 N N21 0.7574(4) 0.3574(4) 0.3848(2) 0.0364(7) Uani d D 1 1 H H21A 0.804(5) 0.391(5) 0.4667(18) 0.044 Uiso d D 1 1 H H21B 0.834(5) 0.412(5) 0.345(3) 0.044 Uiso d D 1 1 N N1' 0.5718(4) 0.2739(4) 0.6578(2) 0.0296(6) Uani d . 1 1 H H1' 0.537(6) 0.248(5) 0.577(4) 0.036 Uiso d . 1 1 C C2' 0.7823(4) 0.3500(4) 0.7204(3) 0.0297(7) Uani d . 1 1 N N3' 0.8400(4) 0.3832(4) 0.8456(2) 0.0300(6) Uani d . 1 1 C C4' 0.6961(4) 0.3299(4) 0.9056(3) 0.0289(7) Uani d . 1 1 C C5' 0.4848(4) 0.2423(5) 0.8380(3) 0.0320(7) Uani d . 1 1 C C6' 0.4223(5) 0.2203(5) 0.7161(3) 0.0342(7) Uani d . 1 1 H H6' 0.2777 0.1688 0.6719 0.041 Uiso calc R 1 1 O O21' 0.9153(3) 0.3898(3) 0.6602(2) 0.0383(6) Uani d . 1 1 N N41' 0.7527(4) 0.3599(4) 1.0271(2) 0.0353(7) Uani d D 1 1 H H41A 0.661(5) 0.320(5) 1.068(3) 0.042 Uiso d D 1 1 H H41B 0.879(4) 0.428(5) 1.064(3) 0.042 Uiso d D 1 1 F F51' 0.3432(3) 0.1872(3) 0.90050(17) 0.0446(6) Uani 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 0.0289(12) 0.0360(14) 0.0332(13) 0.0014(10) 0.0096(10) 0.0107(11) C2 0.0301(14) 0.0324(16) 0.0353(16) 0.0072(11) 0.0133(12) 0.0105(13) N3 0.0247(11) 0.0412(15) 0.0326(13) 0.0005(10) 0.0091(9) 0.0103(11) C4 0.0255(13) 0.0433(18) 0.0325(15) -0.0002(12) 0.0086(11) 0.0101(13) C5 0.0259(13) 0.0413(18) 0.0363(16) -0.0057(12) 0.0044(12) 0.0056(14) C6 0.0308(14) 0.0394(17) 0.0305(15) -0.0020(12) 0.0036(12) 0.0059(13) N21 0.0220(11) 0.0533(17) 0.0353(14) -0.0061(11) 0.0070(10) 0.0154(12) N1' 0.0243(11) 0.0381(14) 0.0247(12) -0.0029(10) 0.0014(9) 0.0095(11) C2' 0.0234(12) 0.0325(16) 0.0345(15) 0.0011(11) 0.0062(11) 0.0118(13) N3' 0.0212(11) 0.0362(14) 0.0331(13) -0.0013(9) 0.0040(9) 0.0124(11) C4' 0.0266(13) 0.0299(15) 0.0321(15) 0.0026(11) 0.0078(11) 0.0108(12) C5' 0.0246(13) 0.0414(17) 0.0330(15) -0.0018(12) 0.0099(11) 0.0129(13) C6' 0.0240(13) 0.0429(18) 0.0356(16) -0.0017(12) 0.0072(11) 0.0107(14) O21' 0.0300(10) 0.0516(14) 0.0380(12) -0.0031(9) 0.0106(9) 0.0188(10) N41' 0.0268(12) 0.0469(16) 0.0322(14) -0.0056(11) 0.0054(10) 0.0130(12) F51' 0.0304(9) 0.0678(14) 0.0373(10) -0.0121(8) 0.0114(8) 0.0164(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 C6 N1 C2 115.8(2) N21 C2 N1 118.8(3) N21 C2 N3 116.3(3) N1 C2 N3 124.8(3) C4 N3 C2 116.6(3) N3 C4 C5 123.1(3) N3 C4 H4 118.4 C5 C4 H4 118.4 C6 C5 C4 115.8(3) C6 C5 H5 122.1 C4 C5 H5 122.1 N1 C6 C5 123.8(3) N1 C6 H6 118.1 C5 C6 H6 118.1 C2 N21 H21A 122(2) C2 N21 H21B 119(2) H21A N21 H21B 116(3) C6' N1' C2' 121.8(2) C6' N1' H1' 119(2) C2' N1' H1' 119(2) O21' C2' N3' 121.8(2) O21' C2' N1' 118.6(3) N3' C2' N1' 119.6(2) C4' N3' C2' 119.8(2) N41' C4' N3' 120.0(3) N41' C4' C5' 120.7(2) N3' C4' C5' 119.3(3) C6' C5' F51' 120.6(3) C6' C5' C4' 121.1(3) F51' C5' C4' 118.3(3) C5' C6' N1' 118.2(3) C5' C6' H6' 120.9 N1' C6' H6' 120.9 C4' N41' H41A 121(2) C4' N41' H41B 116(3) H41A N41' H41B 123(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance N1 C6 1.346(4) N1 C2 1.356(4) C2 N21 1.338(4) C2 N3 1.364(4) N3 C4 1.338(4) C4 C5 1.387(4) C4 H4 0.9500 C5 C6 1.383(4) C5 H5 0.9500 C6 H6 0.9500 N21 H21A 0.894(19) N21 H21B 0.879(19) N1' C6' 1.360(4) N1' C2' 1.380(4) N1' H1' 0.88(4) C2' O21' 1.259(3) C2' N3' 1.369(4) N3' C4' 1.347(4) C4' N41' 1.329(4) C4' C5' 1.419(4) C5' C6' 1.345(4) C5' F51' 1.363(3) C6' H6' 0.9500 N41' H41A 0.899(19) N41' H41B 0.879(19) 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 N21 H21B O21' 2_766 0.879(19) 2.11(2) 2.917(3) 152(3) N21 H21A O21' . 0.894(19) 2.20(2) 3.072(4) 165(3) N1' H1' N3 . 0.88(4) 1.96(4) 2.836(4) 171(3) N41' H41B N3' 2_767 0.879(19) 2.09(2) 2.967(4) 173(3) N41' H41A N1 1_556 0.899(19) 2.25(2) 3.136(3) 168(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 179.4(3) C6 N1 C2 N3 1.4(4) N21 C2 N3 C4 -179.6(3) N1 C2 N3 C4 -1.5(4) C2 N3 C4 C5 0.8(4) N3 C4 C5 C6 -0.1(5) C2 N1 C6 C5 -0.6(4) C4 C5 C6 N1 0.0(5) C6' N1' C2' O21' 177.3(3) C6' N1' C2' N3' -3.7(4) O21' C2' N3' C4' -176.8(3) N1' C2' N3' C4' 4.3(4) C2' N3' C4' N41' 179.2(3) C2' N3' C4' C5' -1.0(4) N41' C4' C5' C6' 176.6(3) N3' C4' C5' C6' -3.2(5) N41' C4' C5' F51' -1.0(4) N3' C4' C5' F51' 179.1(2) F51' C5' C6' N1' -178.6(3) C4' C5' C6' N1' 3.8(5) C2' N1' C6' C5' -0.4(4) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 30654563 2 PubChem 139064071