#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:01:59 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301802 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/51/2105159.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_2105159 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 O2' _chemical_formula_sum 'C8 H9 F N6 O3' _chemical_formula_weight 256.21 _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 101.660(8) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 15.5508(15) _cell_length_b 11.7839(7) _cell_length_c 11.4971(12) _cell_measurement_reflns_used 9090 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 25.85 _cell_measurement_theta_min 3.45 _cell_volume 2063.4(3) _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 0.998 _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 0.1588 _diffrn_reflns_av_sigmaI/netI 0.0674 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 15020 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.59 _diffrn_reflns_theta_min 3.46 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.141 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.650 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1056 _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _refine_diff_density_max 0.271 _refine_diff_density_min -0.214 _refine_ls_extinction_coef 0.0018(5) _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 0.991 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 192 _refine_ls_number_reflns 1935 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.991 _refine_ls_R_factor_all 0.0506 _refine_ls_R_factor_gt 0.0373 _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^)+(0.0472P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0911 _refine_ls_wR_factor_ref 0.0961 _reflns_number_gt 1507 _reflns_number_total 1935 _reflns_threshold_expression I>2sigma(I) _iucr_refine_instructions_details ; TITL mt18-11 in C2/c CELL 0.71073 15.5508 11.7839 11.4971 90.000 101.660 90.000 ZERR 8.00 0.0015 0.0007 0.0012 0.000 0.008 0.000 LATT 7 SYMM -X, Y, 0.5-Z SFAC C H F N O UNIT 64 72 8 48 24 SIZE 0.3 0.3 0.6 REM farbloser Block ACTA 50 L.S. 10 BOND $H CONF FMAP 2 PLAN 10 TEMP -100 EQIV_$1 -x, -y+1, -z+2 EQIV_$2 -x+1/2, y-1/2, -z+3/2 EQIV_$3 -x+1/2, -y+3/2, -z+1 EQIV_$4 x+1/2, -y+1/2, z-1/2 HTAB N1 O21' HTAB N3 O41_$1 HTAB N61 O21_$2 HTAB N61 N3' HTAB N1' O21'_$3 HTAB N41' O41_$4 HTAB N41' O21_$2 WGHT 0.047200 EXTI 0.001762 FVAR 0.19166 N1 4 0.163137 0.506721 0.750012 11.00000 0.02625 0.01747 = 0.02376 0.00034 0.01689 -0.00285 H1 2 0.191281 0.542950 0.699760 11.00000 0.02703 C2 1 0.121061 0.573380 0.818661 11.00000 0.02803 0.01778 = 0.02547 -0.00108 0.01460 -0.00231 N3 4 0.073485 0.517457 0.888795 11.00000 0.02660 0.01659 = 0.02465 0.00065 0.01666 -0.00015 H3 2 0.043738 0.555830 0.939906 11.00000 0.04667 C4 1 0.064323 0.398693 0.892978 11.00000 0.01749 0.01818 = 0.01981 0.00099 0.00803 -0.00221 C5 1 0.109335 0.335374 0.819434 11.00000 0.02088 0.01460 = 0.02464 -0.00059 0.01061 -0.00164 AFIX 43 H5 2 0.104903 0.254962 0.817628 11.00000 -1.20000 AFIX 0 C6 1 0.159423 0.389408 0.750592 11.00000 0.01767 0.01843 = 0.01808 -0.00200 0.00644 -0.00094 O21 5 0.128093 0.678014 0.816161 11.00000 0.05491 0.01504 = 0.04449 -0.00019 0.03494 -0.00398 O41 5 0.018411 0.358822 0.961116 11.00000 0.02625 0.02035 = 0.02822 0.00079 0.01888 -0.00348 N61 4 0.207566 0.337713 0.681263 11.00000 0.02685 0.02027 = 0.03112 -0.00261 0.01900 -0.00101 H61A 2 0.216738 0.262430 0.686686 11.00000 0.06095 H61B 2 0.245553 0.377574 0.644644 11.00000 0.05425 N1' 4 0.326682 0.651646 0.454650 11.00000 0.02278 0.01875 = 0.02392 0.00406 0.01344 0.00127 H1' 2 0.304721 0.729190 0.442713 11.00000 0.04273 C2' 1 0.296441 0.585299 0.537270 11.00000 0.01899 0.01796 = 0.02044 0.00089 0.00939 -0.00017 N3' 4 0.322735 0.475380 0.553396 11.00000 0.02081 0.01492 = 0.02397 -0.00010 0.01190 -0.00029 C4' 1 0.378198 0.431973 0.489345 11.00000 0.01936 0.01794 = 0.02171 -0.00282 0.00862 -0.00167 C5' 1 0.406127 0.500055 0.400882 11.00000 0.02259 0.02803 = 0.02316 -0.00088 0.01543 0.00502 C6' 1 0.380860 0.609226 0.385355 11.00000 0.02390 0.02521 = 0.02397 0.00540 0.01385 0.00045 AFIX 43 H6' 2 0.400147 0.655394 0.327892 11.00000 -1.20000 AFIX 0 O21' 5 0.244959 0.629319 0.596446 11.00000 0.02879 0.01722 = 0.03081 0.00216 0.02007 0.00289 N41' 4 0.407155 0.326272 0.507936 11.00000 0.02944 0.01823 = 0.03328 0.00040 0.02068 0.00356 H41C 2 0.445786 0.299460 0.465809 11.00000 0.04290 H41D 2 0.391268 0.284952 0.566929 11.00000 0.04481 F51' 3 0.460070 0.451328 0.336081 11.00000 0.04775 0.03750 = 0.03758 0.00640 0.03367 0.01557 HKLF 4 REM mt18-11 in C2/c REM R1 = 0.0373 for 1507 Fo > 4sig(Fo) and 0.0506 for all 1935 data REM 192 parameters refined using 0 restraints END ; _cod_data_source_file gp5052.cif _cod_data_source_block IV _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 2.4.2 from 2011-04-26. Automatic conversion script Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius ; _cod_original_sg_symbol_H-M 'C 2/c' _cod_database_code 2105159 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' 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 0.16314(8) 0.50672(12) 0.75001(12) 0.0208(3) Uani d . 1 1 H H1 0.1913(12) 0.5430(16) 0.6998(17) 0.027(5) Uiso d . 1 1 C C2 0.12106(10) 0.57338(13) 0.81866(14) 0.0225(4) Uani d . 1 1 N N3 0.07348(8) 0.51746(11) 0.88880(12) 0.0210(3) Uani d . 1 1 H H3 0.0437(13) 0.5558(18) 0.940(2) 0.047(6) Uiso d . 1 1 C C4 0.06432(9) 0.39869(13) 0.89298(13) 0.0179(3) Uani d . 1 1 C C5 0.10933(9) 0.33537(13) 0.81943(13) 0.0192(3) Uani d . 1 1 H H5 0.1049 0.2550 0.8176 0.023 Uiso calc R 1 1 C C6 0.15942(9) 0.38941(13) 0.75059(13) 0.0177(3) Uani d . 1 1 O O21 0.12809(8) 0.67801(10) 0.81616(11) 0.0347(3) Uani d . 1 1 O O41 0.01841(7) 0.35882(9) 0.96112(10) 0.0231(3) Uani d . 1 1 N N61 0.20757(9) 0.33771(13) 0.68126(13) 0.0242(3) Uani d . 1 1 H H61A 0.2167(15) 0.262(2) 0.687(2) 0.061(7) Uiso d . 1 1 H H61B 0.2456(15) 0.3776(19) 0.645(2) 0.054(7) Uiso d . 1 1 N N1' 0.32668(8) 0.65165(11) 0.45465(12) 0.0206(3) Uani d . 1 1 H H1' 0.3047(13) 0.7292(18) 0.4427(18) 0.043(6) Uiso d . 1 1 C C2' 0.29644(9) 0.58530(13) 0.53727(14) 0.0184(3) Uani d . 1 1 N N3' 0.32273(8) 0.47538(10) 0.55340(12) 0.0189(3) Uani d . 1 1 C C4' 0.37820(9) 0.43197(12) 0.48934(14) 0.0190(3) Uani d . 1 1 C C5' 0.40613(10) 0.50005(15) 0.40088(14) 0.0231(4) Uani d . 1 1 C C6' 0.38086(10) 0.60923(14) 0.38535(14) 0.0231(4) Uani d . 1 1 H H6' 0.4001 0.6554 0.3279 0.028 Uiso calc R 1 1 O O21' 0.24496(7) 0.62932(9) 0.59645(10) 0.0236(3) Uani d . 1 1 N N41' 0.40715(9) 0.32627(12) 0.50794(14) 0.0250(3) Uani d . 1 1 H H41C 0.4458(14) 0.2995(18) 0.4658(19) 0.043(6) Uiso d . 1 1 H H41D 0.3913(14) 0.2850(18) 0.567(2) 0.045(6) Uiso d . 1 1 F F51' 0.46007(7) 0.45133(9) 0.33608(9) 0.0374(3) 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 0.0262(7) 0.0175(7) 0.0238(7) -0.0028(5) 0.0169(6) 0.0003(5) C2 0.0280(8) 0.0178(8) 0.0255(8) -0.0023(6) 0.0146(7) -0.0011(6) N3 0.0266(7) 0.0166(7) 0.0247(7) -0.0002(5) 0.0167(6) 0.0007(5) C4 0.0175(7) 0.0182(7) 0.0198(8) -0.0022(6) 0.0080(6) 0.0010(6) C5 0.0209(7) 0.0146(7) 0.0246(8) -0.0016(6) 0.0106(6) -0.0006(6) C6 0.0177(7) 0.0184(8) 0.0181(8) -0.0009(6) 0.0064(6) -0.0020(6) O21 0.0549(8) 0.0150(6) 0.0445(7) -0.0040(5) 0.0349(6) -0.0002(5) O41 0.0263(6) 0.0204(6) 0.0282(6) -0.0035(4) 0.0189(5) 0.0008(5) N61 0.0268(7) 0.0203(7) 0.0311(8) -0.0010(6) 0.0190(6) -0.0026(6) N1' 0.0228(7) 0.0187(7) 0.0239(7) 0.0013(5) 0.0134(5) 0.0041(5) C2' 0.0190(7) 0.0180(8) 0.0204(8) -0.0002(6) 0.0094(6) 0.0009(6) N3' 0.0208(6) 0.0149(6) 0.0240(7) -0.0003(5) 0.0119(5) -0.0001(5) C4' 0.0194(7) 0.0179(8) 0.0217(8) -0.0017(6) 0.0086(6) -0.0028(6) C5' 0.0226(8) 0.0280(8) 0.0232(8) 0.0050(6) 0.0154(7) -0.0009(7) C6' 0.0239(7) 0.0252(8) 0.0240(8) 0.0005(7) 0.0138(6) 0.0054(7) O21' 0.0288(6) 0.0172(6) 0.0308(6) 0.0029(4) 0.0201(5) 0.0022(5) N41' 0.0294(8) 0.0182(7) 0.0333(8) 0.0036(6) 0.0207(6) 0.0004(6) F51' 0.0477(6) 0.0375(6) 0.0376(6) 0.0156(5) 0.0337(5) 0.0064(5) 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 123.01(13) C2 N1 H1 116.7(12) C6 N1 H1 120.2(12) O21 C2 N3 123.62(15) O21 C2 N1 120.18(14) N3 C2 N1 116.19(14) C2 N3 C4 124.68(13) C2 N3 H3 122.2(13) C4 N3 H3 113.1(13) O41 C4 N3 117.92(13) O41 C4 C5 126.10(14) N3 C4 C5 115.98(13) C6 C5 C4 120.43(14) C6 C5 H5 119.8 C4 C5 H5 119.8 N61 C6 C5 125.44(15) N61 C6 N1 114.90(14) C5 C6 N1 119.66(14) C6 N61 H61A 120.4(16) C6 N61 H61B 121.7(14) H61A N61 H61B 115(2) C6' N1' C2' 121.93(14) C6' N1' H1' 120.0(12) C2' N1' H1' 117.9(12) O21' C2' N3' 121.60(14) O21' C2' N1' 118.58(13) N3' C2' N1' 119.82(13) C4' N3' C2' 119.78(13) N41' C4' N3' 120.24(14) N41' C4' C5' 119.94(14) N3' C4' C5' 119.81(13) C6' C5' F51' 121.85(15) C6' C5' C4' 120.52(14) F51' C5' C4' 117.61(14) C5' C6' N1' 118.05(15) C5' C6' H6' 121.0 N1' C6' H6' 121.0 C4' N41' H41C 118.9(14) C4' N41' H41D 119.2(13) H41C N41' H41D 121.6(19) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance N1 C2 1.370(2) N1 C6 1.384(2) N1 H1 0.90(2) C2 O21 1.239(2) C2 N3 1.369(2) N3 C4 1.4085(19) N3 H3 0.93(2) C4 O41 1.2531(18) C4 C5 1.415(2) C5 C6 1.374(2) C5 H5 0.9500 C6 N61 1.345(2) N61 H61A 0.90(2) N61 H61B 0.92(3) N1' C6' 1.366(2) N1' C2' 1.384(2) N1' H1' 0.98(2) C2' O21' 1.2622(18) C2' N3' 1.3597(19) N3' C4' 1.3433(19) C4' N41' 1.327(2) C4' C5' 1.430(2) C5' C6' 1.346(2) C5' F51' 1.3569(18) C6' H6' 0.9500 N41' H41C 0.90(2) N41' H41D 0.91(2) 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 N1 H1 O21' . 0.90(2) 1.88(2) 2.7805(17) 175.4(17) N3 H3 O41 5_567 0.93(2) 1.92(2) 2.8534(17) 176.9(19) N61 H61A O21 4_546 0.90(2) 2.62(2) 3.1691(18) 120.6(18) N61 H61B N3' . 0.92(3) 2.09(3) 3.011(2) 175.2(19) N1' H1' O21' 7_566 0.98(2) 1.85(2) 2.8256(17) 173.3(18) N41' H41C O41 8 0.90(2) 2.19(2) 2.9012(17) 135.7(18) N41' H41D O21 4_546 0.91(2) 1.91(2) 2.809(2) 169.7(19) 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 O21 178.62(15) C6 N1 C2 N3 -0.5(2) O21 C2 N3 C4 179.83(15) N1 C2 N3 C4 -1.1(2) C2 N3 C4 O41 -179.74(13) C2 N3 C4 C5 0.9(2) O41 C4 C5 C6 -178.43(14) N3 C4 C5 C6 0.9(2) C4 C5 C6 N61 177.24(14) C4 C5 C6 N1 -2.4(2) C2 N1 C6 N61 -177.43(14) C2 N1 C6 C5 2.2(2) C6' N1' C2' O21' -178.42(13) C6' N1' C2' N3' 1.9(2) O21' C2' N3' C4' -179.43(13) N1' C2' N3' C4' 0.3(2) C2' N3' C4' N41' 177.16(14) C2' N3' C4' C5' -2.8(2) N41' C4' C5' C6' -176.55(15) N3' C4' C5' C6' 3.4(2) N41' C4' C5' F51' 2.0(2) N3' C4' C5' F51' -178.07(13) F51' C5' C6' N1' -179.78(13) C4' C5' C6' N1' -1.3(2) C2' N1' C6' C5' -1.3(2) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 30654565 2 PubChem 139064073