#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:01:59 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301802 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/51/2105157.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_2105157 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 'C6 H9 N3 O2' _chemical_formula_sum 'C6 H9 N3 O2' _chemical_formula_weight 155.16 _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' _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 111.266(13) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.9835(14) _cell_length_b 10.0664(12) _cell_length_c 9.8380(16) _cell_measurement_reflns_used 2797 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 25.81 _cell_measurement_theta_min 3.4 _cell_volume 736.8(2) _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 0.996 _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 0.0748 _diffrn_reflns_av_sigmaI/netI 0.0581 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 4148 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.59 _diffrn_reflns_theta_min 3.41 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.108 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.399 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 328 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.206 _refine_diff_density_min -0.277 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.965 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 107 _refine_ls_number_reflns 1378 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.965 _refine_ls_R_factor_all 0.0611 _refine_ls_R_factor_gt 0.0477 _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^)+(0.0753P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1122 _refine_ls_wR_factor_ref 0.1180 _reflns_number_gt 1081 _reflns_number_total 1378 _reflns_threshold_expression I>2\s(I) _iucr_refine_instructions_details ; TITL pk1-31 in P2(1)/n CELL 0.71073 7.9835 10.0664 9.8380 90.000 111.266 90.000 ZERR 4.00 0.0014 0.0012 0.0016 0.000 0.013 0.000 LATT 1 SYMM 0.5-X, 0.5+Y, 0.5-Z SFAC C H N O UNIT 24 36 12 8 REM farbloser Block SIZE 0.2 0.2 0.4 ACTA 50 L.S. 10 BOND $H FMAP 2 PLAN 10 TEMP -100 HFIX 23 -1.2 C3 HFIX 137 -1.5 C53 EQIV_$1 -x, -y+1, -z+1 HTAB N1 O54_$1 HTAB N1 O54 WGHT 0.075300 FVAR 0.59097 0.73616 N1 3 0.30396 0.43048 0.60310 11.00000 0.01785 0.02214 = 0.02680 0.00146 0.00413 0.00286 H1 2 0.21157 0.48148 0.56536 11.00000 0.04525 C2 1 0.47776 0.47782 0.65179 11.00000 0.02038 0.02756 = 0.02015 -0.00066 0.00613 -0.00250 C3 1 0.59846 0.35708 0.70209 11.00000 0.01922 0.02715 = 0.02806 0.00360 0.00562 -0.00044 N4 3 0.46996 0.24849 0.66956 11.00000 0.01807 0.02404 = 0.03083 0.00287 0.00464 0.00206 C5 1 0.29992 0.29309 0.61126 11.00000 0.02149 0.02200 = 0.02081 -0.00044 0.00706 0.00295 O21 4 0.52338 0.59333 0.65255 11.00000 0.02520 0.02815 = 0.03590 -0.00049 0.00673 -0.00430 C41 1 0.51785 0.10923 0.69727 11.00000 0.02272 0.02898 = 0.03717 0.00463 0.00830 0.00598 AFIX 137 PART 1 H41A 2 0.63921 0.10195 0.77099 21.00000 -1.50000 H41B 2 0.51455 0.06663 0.60676 21.00000 -1.50000 H41C 2 0.43211 0.06517 0.73274 21.00000 -1.50000 PART 2 H41D 2 0.41805 0.05388 0.63597 -21.00000 -1.50000 H41E 2 0.54265 0.08920 0.80022 -21.00000 -1.50000 H41F 2 0.62516 0.09068 0.67429 -21.00000 -1.50000 AFIX 0 PART 0 N51 3 0.16103 0.21042 0.56779 11.00000 0.01915 0.02125 = 0.02781 -0.00095 0.00612 0.00120 C52 1 -0.01004 0.26064 0.53375 11.00000 0.02135 0.02219 = 0.02191 0.00216 0.00674 0.00055 C53 1 -0.15797 0.16039 0.47183 11.00000 0.02057 0.02785 = 0.03124 -0.00154 0.00561 -0.00215 O54 4 -0.04656 0.37641 0.55588 11.00000 0.02047 0.02278 = 0.05210 -0.00132 0.00922 0.00227 HKLF 4 END ; _cod_data_source_file gp5052.cif _cod_data_source_block II _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 'P 21/n' _cod_database_code 2105157 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -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 _atom_site_disorder_assembly _atom_site_disorder_group N N1 0.3040(2) 0.43048(16) 0.60310(15) 0.0234(4) Uani d . 1 1 . . H H1 0.212(4) 0.481(2) 0.565(3) 0.045(7) Uiso d . 1 1 . . C C2 0.4778(2) 0.47782(19) 0.65179(17) 0.0230(4) Uani d . 1 1 . . C C3 0.5985(2) 0.35708(18) 0.70209(19) 0.0256(4) Uani d . 1 1 . . H H3A 0.6802 0.3480 0.6473 0.031 Uiso calc R 1 1 . . H H3B 0.6706 0.3618 0.8077 0.031 Uiso calc R 1 1 . . N N4 0.46996(19) 0.24849(15) 0.66956(16) 0.0255(4) Uani d . 1 1 . . C C5 0.2999(2) 0.29309(18) 0.61126(17) 0.0216(4) Uani d . 1 1 . . O O21 0.52338(16) 0.59333(14) 0.65255(13) 0.0310(4) Uani d . 1 1 . . C C41 0.5179(3) 0.10924(19) 0.6973(2) 0.0303(4) Uani d . 1 1 . . H H41A 0.6392 0.1020 0.7710 0.046 Uiso calc PR 0.74(2) 1 A 1 H H41B 0.5146 0.0666 0.6068 0.046 Uiso calc PR 0.74(2) 1 A 1 H H41C 0.4321 0.0652 0.7327 0.046 Uiso calc PR 0.74(2) 1 A 1 H H41D 0.4181 0.0539 0.6360 0.046 Uiso d PR 0.26(2) 1 A 2 H H41E 0.5426 0.0892 0.8002 0.046 Uiso d PR 0.26(2) 1 A 2 H H41F 0.6252 0.0907 0.6743 0.046 Uiso d PR 0.26(2) 1 A 2 N N51 0.16103(19) 0.21043(15) 0.56779(15) 0.0234(4) Uani d . 1 1 . . C C52 -0.0100(2) 0.26064(17) 0.53375(17) 0.0221(4) Uani d . 1 1 . . C C53 -0.1580(2) 0.16038(18) 0.4718(2) 0.0276(4) Uani d . 1 1 . . H H53A -0.1880 0.1208 0.5511 0.041 Uiso calc R 1 1 . . H H53B -0.1179 0.0906 0.4211 0.041 Uiso calc R 1 1 . . H H53C -0.2644 0.2044 0.4029 0.041 Uiso calc R 1 1 . . O O54 -0.04656(17) 0.37642(13) 0.55588(15) 0.0329(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 0.0179(8) 0.0221(9) 0.0268(7) 0.0029(6) 0.0041(6) 0.0015(6) C2 0.0204(9) 0.0276(10) 0.0202(8) -0.0025(7) 0.0061(6) -0.0007(6) C3 0.0192(9) 0.0271(11) 0.0281(9) -0.0004(7) 0.0056(7) 0.0036(7) N4 0.0181(7) 0.0240(9) 0.0308(8) 0.0021(6) 0.0046(6) 0.0029(6) C5 0.0215(9) 0.0220(10) 0.0208(8) 0.0030(7) 0.0071(6) -0.0004(6) O21 0.0252(7) 0.0282(8) 0.0359(7) -0.0043(5) 0.0067(5) -0.0005(5) C41 0.0227(9) 0.0290(11) 0.0372(10) 0.0060(8) 0.0083(7) 0.0046(8) N51 0.0191(7) 0.0213(9) 0.0278(7) 0.0012(6) 0.0061(6) -0.0010(6) C52 0.0214(9) 0.0222(10) 0.0219(8) 0.0006(7) 0.0067(7) 0.0022(6) C53 0.0206(9) 0.0279(11) 0.0312(9) -0.0022(7) 0.0056(7) -0.0015(7) O54 0.0205(7) 0.0228(7) 0.0521(8) 0.0023(5) 0.0092(6) -0.0013(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' 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 C5 111.50(14) C2 N1 H1 122.6(17) C5 N1 H1 125.7(17) O21 C2 N1 126.41(16) O21 C2 C3 127.55(15) N1 C2 C3 106.05(15) N4 C3 C2 102.51(14) N4 C3 H3A 111.3 C2 C3 H3A 111.3 N4 C3 H3B 111.3 C2 C3 H3B 111.3 H3A C3 H3B 109.2 C5 N4 C41 123.95(15) C5 N4 C3 111.44(15) C41 N4 C3 124.60(14) N51 C5 N4 121.62(17) N51 C5 N1 129.88(15) N4 C5 N1 108.46(14) N4 C41 H41A 109.5 N4 C41 H41B 109.5 N4 C41 H41C 109.5 N4 C41 H41D 109.5 N4 C41 H41E 109.5 H41D C41 H41E 109.5 N4 C41 H41F 109.5 H41D C41 H41F 109.5 H41E C41 H41F 109.5 C5 N51 C52 119.12(16) O54 C52 N51 125.27(16) O54 C52 C53 120.12(15) N51 C52 C53 114.55(15) C52 C53 H53A 109.5 C52 C53 H53B 109.5 H53A C53 H53B 109.5 C52 C53 H53C 109.5 H53A C53 H53C 109.5 H53B C53 H53C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance N1 C2 1.378(2) N1 C5 1.386(2) N1 H1 0.86(3) C2 O21 1.218(2) C2 C3 1.518(2) C3 N4 1.453(2) C3 H3A 0.9900 C3 H3B 0.9900 N4 C5 1.345(2) N4 C41 1.453(2) C5 N51 1.327(2) C41 H41A 0.9800 C41 H41B 0.9800 C41 H41C 0.9800 C41 H41D 0.9800 C41 H41E 0.9799 C41 H41F 0.9800 N51 C52 1.379(2) C52 O54 1.240(2) C52 C53 1.504(2) C53 H53A 0.9800 C53 H53B 0.9800 C53 H53C 0.9800 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 O54 3_566 0.86(3) 2.02(3) 2.849(2) 162(2) N1 H1 O54 . 0.86(3) 2.29(2) 2.720(2) 111.0(19) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 736895