#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:01:59 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301802 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/51/2105169.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_2105169 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_paper_doi 10.1107/S0108768112029977 _journal_volume 68 _journal_year 2012 _chemical_formula_moiety 'C4 H4 F N3 O, C5 H7 N3 O' _chemical_formula_sum 'C9 H11 F N6 O2' _chemical_formula_weight 254.24 _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 75.967(13) _cell_angle_beta 89.785(13) _cell_angle_gamma 82.918(13) _cell_formula_units_Z 2 _cell_length_a 4.5285(7) _cell_length_b 10.1491(17) _cell_length_c 12.626(2) _cell_measurement_reflns_used 3861 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 25.87 _cell_measurement_theta_min 3.47 _cell_volume 558.47(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 0.995 _diffrn_measured_fraction_theta_max 0.992 _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 0.1130 _diffrn_reflns_av_sigmaI/netI 0.0845 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 4506 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.59 _diffrn_reflns_theta_min 3.47 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.123 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.512 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 264 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _refine_diff_density_max 0.320 _refine_diff_density_min -0.312 _refine_ls_extinction_coef 0.09(2) _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 0.957 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 189 _refine_ls_number_reflns 2099 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.957 _refine_ls_R_factor_all 0.0734 _refine_ls_R_factor_gt 0.0634 _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^)+(0.1288P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1653 _refine_ls_wR_factor_ref 0.1746 _reflns_number_gt 1675 _reflns_number_total 2099 _reflns_threshold_expression I>2sigma(I) _iucr_refine_instructions_details ; TITL mt22-20trans in P-1 CELL 0.71073 4.5285 10.1491 12.626 75.967 89.785 82.918 ZERR 2.00 0.0007 0.0017 0.002 0.013 0.013 0.013 LATT 1 SFAC C H F N O UNIT 18 22 2 12 4 L.S. 10 BOND $H CONF FMAP 2 PLAN 10 REM farbloser Block SIZE 0.3 0.3 0.3 ACTA 50 EQIV_$1 -x, -y+1, -z+1 EQIV_$2 -x+2, -y+2, -z+1 EQIV_$3 -x+1, -y+1, -z+2 HTAB N1' O21'_$1 HTAB N41' O41_$2 HTAB N41' O41 HTAB N3 N3' HTAB N21 N1_$3 HTAB N21 O21' TEMP -100 WGHT 0.128800 EXTI 0.105091 FVAR 1.21038 N1 4 0.694992 0.647904 0.946255 11.00000 0.03393 0.03216 = 0.02334 -0.00451 -0.00404 -0.00722 C2 1 0.592262 0.648419 0.846866 11.00000 0.02678 0.02658 = 0.02542 -0.00543 -0.00167 -0.00395 N3 4 0.656375 0.741301 0.754908 11.00000 0.03014 0.02778 = 0.02144 -0.00476 -0.00483 -0.00881 H3 2 0.584753 0.735638 0.687219 11.00000 0.04300 C4 1 0.834660 0.843386 0.756573 11.00000 0.02827 0.02494 = 0.02814 -0.00685 -0.00414 -0.00558 C5 1 0.939321 0.844791 0.862852 11.00000 0.03271 0.03223 = 0.02796 -0.00835 -0.00726 -0.01047 AFIX 43 H5 2 1.057064 0.912746 0.871921 11.00000 -1.20000 AFIX 0 C6 1 0.868602 0.747674 0.951133 11.00000 0.03066 0.03142 = 0.02790 -0.01000 -0.00404 -0.00272 N21 4 0.423810 0.551937 0.835420 11.00000 0.04094 0.03463 = 0.02476 -0.00276 -0.00488 -0.01481 H21A 2 0.378858 0.482416 0.900541 11.00000 0.04404 H21B 2 0.345756 0.561438 0.770588 11.00000 0.05236 O41 5 0.890513 0.922405 0.668851 11.00000 0.04166 0.03555 = 0.02381 -0.00300 -0.00395 -0.01877 C61 1 0.985934 0.740987 1.064187 11.00000 0.04709 0.04682 = 0.02582 -0.00845 -0.00697 -0.01254 AFIX 137 H61A 2 1.106970 0.815448 1.061007 11.00000 -1.50000 H61B 2 1.108430 0.652832 1.092614 11.00000 -1.50000 H61C 2 0.818647 0.750336 1.112407 11.00000 -1.50000 AFIX 0 N1' 4 0.205613 0.620396 0.425320 11.00000 0.02956 0.02896 = 0.02618 -0.00869 -0.00731 -0.00819 H1' 2 0.098274 0.555682 0.418863 11.00000 0.04154 C2' 1 0.273058 0.636219 0.528172 11.00000 0.02345 0.02473 = 0.02761 -0.00783 -0.00659 -0.00276 N3' 4 0.457594 0.729298 0.537360 11.00000 0.02332 0.02709 = 0.02631 -0.00674 -0.00594 -0.00615 C4' 1 0.568438 0.806890 0.447899 11.00000 0.02274 0.02308 = 0.02672 -0.00651 -0.00553 -0.00084 C5' 1 0.490377 0.791229 0.341455 11.00000 0.03255 0.02819 = 0.02304 -0.00439 -0.00343 -0.00451 C6' 1 0.312670 0.697283 0.333336 11.00000 0.03147 0.03029 = 0.02657 -0.00984 -0.00741 -0.00444 AFIX 43 H6' 2 0.262323 0.684757 0.263767 11.00000 -1.20000 AFIX 0 O21' 5 0.165200 0.563551 0.610708 11.00000 0.03183 0.03318 = 0.02551 -0.00615 -0.00338 -0.01472 N41' 4 0.751580 0.895096 0.457745 11.00000 0.02920 0.03013 = 0.02600 -0.00709 -0.00296 -0.01180 H411 2 0.828930 0.955521 0.399023 11.00000 0.03333 H412 2 0.792405 0.900485 0.526581 11.00000 0.05234 F51' 3 0.603481 0.871702 0.253175 11.00000 0.04583 0.04357 = 0.02449 -0.00711 0.00172 -0.01796 HKLF 4 REM mt22-20trans in P-1 REM R1 = 0.0683 for 1675 Fo > 4sig(Fo) and 0.0784 for all 2099 data REM 189 parameters refined using 0 restraints END ; _cod_data_source_file gp5053.cif _cod_data_source_block IVa _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 2105169 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 0.6949(4) 0.64793(19) 0.94621(13) 0.0305(5) Uani d . 1 1 C C2 0.5925(4) 0.6483(2) 0.84691(17) 0.0269(5) Uani d . 1 1 N N3 0.6565(4) 0.74133(18) 0.75499(14) 0.0271(4) Uani d . 1 1 H H3 0.586(6) 0.736(3) 0.687(2) 0.041(7) Uiso d . 1 1 C C4 0.8347(4) 0.8433(2) 0.75656(16) 0.0277(5) Uani d . 1 1 C C5 0.9394(5) 0.8449(2) 0.86280(16) 0.0308(5) Uani d . 1 1 H H5 1.0570 0.9129 0.8719 0.037 Uiso calc R 1 1 C C6 0.8686(5) 0.7476(2) 0.95109(16) 0.0303(5) Uani d . 1 1 N N21 0.4238(4) 0.5519(2) 0.83545(16) 0.0340(5) Uani d . 1 1 H H21A 0.381(6) 0.482(3) 0.900(2) 0.045(7) Uiso d . 1 1 H H21B 0.349(7) 0.560(3) 0.770(3) 0.049(8) Uiso d . 1 1 O O41 0.8906(3) 0.92251(16) 0.66884(12) 0.0341(4) Uani d . 1 1 C C61 0.9858(6) 0.7410(3) 1.06419(18) 0.0400(6) Uani d . 1 1 H H61A 1.1054 0.8159 1.0611 0.060 Uiso calc R 1 1 H H61B 1.1096 0.6531 1.0924 0.060 Uiso calc R 1 1 H H61C 0.8184 0.7496 1.1125 0.060 Uiso calc R 1 1 N N1' 0.2056(4) 0.62033(19) 0.42542(14) 0.0283(4) Uani d . 1 1 H H1' 0.098(6) 0.556(3) 0.419(2) 0.039(7) Uiso d . 1 1 C C2' 0.2731(4) 0.6363(2) 0.52814(16) 0.0256(5) Uani d . 1 1 N N3' 0.4576(4) 0.72922(17) 0.53736(13) 0.0260(4) Uani d . 1 1 C C4' 0.5685(4) 0.8070(2) 0.44786(17) 0.0250(5) Uani d . 1 1 C C5' 0.4905(5) 0.7911(2) 0.34156(16) 0.0288(5) Uani d . 1 1 C C6' 0.3126(5) 0.6974(2) 0.33332(17) 0.0296(5) Uani d . 1 1 H H6' 0.2620 0.6851 0.2637 0.036 Uiso calc R 1 1 O O21' 0.1652(3) 0.56351(15) 0.61065(11) 0.0303(4) Uani d . 1 1 N N41' 0.7516(4) 0.89500(18) 0.45773(15) 0.0285(5) Uani d . 1 1 H H411 0.826(6) 0.956(3) 0.399(2) 0.037(7) Uiso d . 1 1 H H412 0.789(6) 0.901(3) 0.526(2) 0.043(7) Uiso d . 1 1 F F51' 0.6035(3) 0.87174(14) 0.25321(10) 0.0380(4) 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 0.0335(10) 0.0336(10) 0.0241(9) -0.0074(8) -0.0029(7) -0.0046(7) C2 0.0267(10) 0.0280(11) 0.0255(10) -0.0045(8) -0.0005(7) -0.0051(8) N3 0.0302(9) 0.0293(10) 0.0222(9) -0.0088(7) -0.0043(7) -0.0043(7) C4 0.0279(10) 0.0268(10) 0.0287(11) -0.0061(8) -0.0028(8) -0.0060(8) C5 0.0321(10) 0.0336(11) 0.0288(11) -0.0112(9) -0.0063(8) -0.0077(9) C6 0.0305(10) 0.0329(11) 0.0280(11) -0.0031(8) -0.0035(8) -0.0089(9) N21 0.0410(10) 0.0359(11) 0.0253(10) -0.0153(8) -0.0040(8) -0.0023(8) O41 0.0415(9) 0.0366(9) 0.0254(8) -0.0188(7) -0.0033(6) -0.0029(6) C61 0.0470(13) 0.0477(14) 0.0267(11) -0.0126(10) -0.0057(9) -0.0085(9) N1' 0.0291(9) 0.0302(9) 0.0278(9) -0.0085(7) -0.0061(7) -0.0085(7) C2' 0.0231(9) 0.0262(10) 0.0282(11) -0.0038(8) -0.0051(7) -0.0074(8) N3' 0.0235(8) 0.0284(9) 0.0271(9) -0.0065(7) -0.0052(7) -0.0068(7) C4' 0.0225(9) 0.0252(10) 0.0269(10) -0.0011(7) -0.0048(7) -0.0062(8) C5' 0.0318(10) 0.0297(11) 0.0237(10) -0.0048(8) -0.0023(8) -0.0037(8) C6' 0.0311(11) 0.0319(11) 0.0271(10) -0.0057(8) -0.0063(8) -0.0088(8) O21' 0.0316(8) 0.0342(9) 0.0272(8) -0.0149(6) -0.0027(6) -0.0059(6) N41' 0.0292(9) 0.0320(10) 0.0265(10) -0.0121(7) -0.0025(7) -0.0070(7) F51' 0.0456(8) 0.0452(8) 0.0255(7) -0.0185(6) 0.0028(5) -0.0069(6) 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 116.15(18) N1 C2 N21 119.53(19) N1 C2 N3 122.68(19) N21 C2 N3 117.78(18) C2 N3 C4 122.83(18) C2 N3 H3 119.7(17) C4 N3 H3 117.4(17) O41 C4 N3 119.30(18) O41 C4 C5 126.09(19) N3 C4 C5 114.61(18) C6 C5 C4 119.25(19) C6 C5 H5 120.4 C4 C5 H5 120.4 C5 C6 N1 124.45(18) C5 C6 C61 121.21(19) N1 C6 C61 114.34(18) C2 N21 H21A 119.4(16) C2 N21 H21B 117(2) H21A N21 H21B 124(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' 121.81(18) C6' N1' H1' 118.5(18) C2' N1' H1' 119.7(18) O21' C2' N3' 121.59(17) O21' C2' N1' 119.28(18) N3' C2' N1' 119.12(19) C4' N3' C2' 120.62(17) N41' C4' N3' 120.17(18) N41' C4' C5' 120.3(2) N3' C4' C5' 119.48(19) C6' C5' F51' 122.49(18) C6' C5' C4' 119.5(2) F51' C5' C4' 118.00(19) C5' C6' N1' 119.44(19) C5' C6' H6' 120.3 N1' C6' H6' 120.3 C4' N41' H411 124.4(16) C4' N41' H412 116.1(19) H411 N41' H412 119(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance N1 C2 1.337(3) N1 C6 1.368(3) C2 N21 1.348(3) C2 N3 1.362(3) N3 C4 1.392(3) N3 H3 0.93(3) C4 O41 1.246(3) C4 C5 1.429(3) C5 C6 1.365(3) C5 H5 0.9500 C6 C61 1.509(3) N21 H21A 0.98(3) N21 H21B 0.88(3) C61 H61A 0.9800 C61 H61B 0.9800 C61 H61C 0.9800 N1' C6' 1.359(3) N1' C2' 1.385(3) N1' H1' 0.88(3) C2' O21' 1.258(3) C2' N3' 1.360(3) N3' C4' 1.346(3) C4' N41' 1.319(3) C4' C5' 1.440(3) C5' C6' 1.342(3) C5' F51' 1.354(2) C6' H6' 0.9500 N41' H411 0.93(3) N41' H412 0.90(3) 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' 2_566 0.88(3) 1.90(3) 2.775(2) 172(3) N41' H411 O41 2_776 0.93(3) 1.94(3) 2.810(2) 154(2) N41' H412 O41 . 0.90(3) 1.93(3) 2.828(2) 176(3) N3 H3 N3' . 0.93(3) 2.00(3) 2.930(2) 176(2) N21 H21A N1 2_667 0.98(3) 2.12(3) 3.090(3) 171(2) N21 H21B O21' . 0.88(3) 2.17(3) 3.045(2) 176(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 178.94(19) C6 N1 C2 N3 0.3(3) N1 C2 N3 C4 0.3(3) N21 C2 N3 C4 -178.35(18) C2 N3 C4 O41 178.00(18) C2 N3 C4 C5 -1.5(3) O41 C4 C5 C6 -177.3(2) N3 C4 C5 C6 2.1(3) C4 C5 C6 N1 -1.7(3) C4 C5 C6 C61 177.1(2) C2 N1 C6 C5 0.4(3) C2 N1 C6 C61 -178.48(19) C6' N1' C2' O21' 179.10(18) C6' N1' C2' N3' -1.7(3) O21' C2' N3' C4' -179.39(17) N1' C2' N3' C4' 1.4(3) C2' N3' C4' N41' -178.74(18) C2' N3' C4' C5' 0.0(3) N41' C4' C5' C6' 177.53(19) N3' C4' C5' C6' -1.2(3) N41' C4' C5' F51' -1.9(3) N3' C4' C5' F51' 179.40(17) F51' C5' C6' N1' -179.68(17) C4' C5' C6' N1' 1.0(3) C2' N1' C6' C5' 0.5(3) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 30654570 2 PubChem 139064080