#------------------------------------------------------------------------------ #$Date: 2012-09-06 16:55:08 +0300 (Thu, 06 Sep 2012) $ #$Revision: 65855 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/10/51/2105164.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_2105164 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_issue 4 _journal_name_full 'Acta Crystallographica Section B' _journal_page_first 431 _journal_page_last 443 _journal_volume 68 _journal_year 2012 _chemical_formula_moiety 'C8 H11 N5 O3' _chemical_formula_sum 'C8 H11 N5 O3' _chemical_formula_weight 225.22 _chemical_name_systematic ; ? ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/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 108.346(8) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 10.9182(11) _cell_length_b 11.1666(8) _cell_length_c 7.9786(9) _cell_measurement_reflns_used 3262 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 25.91 _cell_measurement_theta_min 3.33 _cell_volume 923.30(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 0.998 _diffrn_measured_fraction_theta_max 0.998 _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 0.1316 _diffrn_reflns_av_sigmaI/netI 0.0890 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_number 6501 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.56 _diffrn_reflns_theta_min 3.33 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.128 _exptl_absorpt_correction_type none _exptl_crystal_density_diffrn 1.620 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.266 _refine_diff_density_min -0.315 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.989 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 155 _refine_ls_number_reflns 1723 _refine_ls_number_restraints 3 _refine_ls_restrained_S_all 0.989 _refine_ls_R_factor_all 0.0861 _refine_ls_R_factor_gt 0.0575 _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^)+(0.0711P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1266 _refine_ls_wR_factor_ref 0.1398 _reflns_number_gt 1215 _reflns_number_total 1723 _reflns_threshold_expression I>2sigma(I) _iucr_refine_instructions_details ; TITL mt27-37trans in P2(1)/c CELL 0.71073 10.9182 11.1666 7.9786 90.000 108.346 90.000 ZERR 4.00 0.0011 0.0008 0.0009 0.000 0.008 0.000 LATT 1 SYMM -X, 0.5+Y, 0.5-Z SFAC C H N O UNIT 32 44 20 12 REM farbloser Block SIZE 0.1 0.1 0.2 ACTA 50 L.S. 10 CONF BOND $H FMAP 2 PLAN 10 TEMP -100 DFIX 0.88 0.02 N1 H1 N21 H21A N21 H21B EQIV_$1 -x+2, y-1/2, -z+3/2 EQIV_$2 -x+1, y-1/2, -z+1/2 EQIV_$3 x-1, -y+3/2, z-1/2 HTAB N1 N7_$1 HTAB N21 O95_$2 HTAB N21 O61_$1 HTAB O95 O61_$3 WGHT 0.071100 FVAR 0.41666 N1 3 0.938881 0.622677 0.657256 11.00000 0.01394 0.01334 = 0.02221 0.00054 0.00260 0.00017 H1 2 0.988790 0.564227 0.716161 11.00000 -1.20000 C2 1 0.828427 0.594509 0.524278 11.00000 0.01558 0.01579 = 0.02082 -0.00222 0.00829 0.00126 N3 3 0.749763 0.675385 0.424083 11.00000 0.01773 0.01479 = 0.01959 -0.00124 0.00526 -0.00086 C4 1 0.790334 0.788561 0.471401 11.00000 0.01626 0.01682 = 0.01776 0.00248 0.00739 0.00072 C5 1 0.898087 0.825765 0.604680 11.00000 0.01505 0.01323 = 0.02152 -0.00215 0.00536 -0.00434 C6 1 0.983130 0.738120 0.705810 11.00000 0.01497 0.01606 = 0.01858 0.00073 0.00454 -0.00026 N7 3 0.904816 0.950158 0.611740 11.00000 0.01846 0.01205 = 0.02507 -0.00083 0.00515 -0.00191 C8 1 0.803621 0.986116 0.483896 11.00000 0.01765 0.01106 = 0.02516 0.00132 0.00696 -0.00022 AFIX 43 H8 2 0.783031 1.067958 0.456545 11.00000 -1.20000 AFIX 0 N9 3 0.730000 0.891959 0.393048 11.00000 0.01778 0.01422 = 0.02024 0.00164 0.00498 0.00152 N21 3 0.798940 0.477819 0.499020 11.00000 0.02260 0.01297 = 0.02604 -0.00081 -0.00031 -0.00019 H21A 2 0.727483 0.459389 0.418950 11.00000 -1.20000 H21B 2 0.851549 0.421759 0.560590 11.00000 -1.20000 O61 4 1.087287 0.754852 0.826191 11.00000 0.01863 0.01884 = 0.02809 0.00027 0.00003 -0.00212 C91 1 0.611657 0.897623 0.243399 11.00000 0.01761 0.01806 = 0.01647 0.00259 0.00486 0.00200 AFIX 23 H91A 2 0.624219 0.955038 0.155682 11.00000 -1.20000 H91B 2 0.595194 0.817878 0.186484 11.00000 -1.20000 AFIX 0 O92 4 0.502377 0.932584 0.289665 11.00000 0.01619 0.01527 = 0.02405 0.00191 0.00434 0.00190 C93 1 0.472503 0.857331 0.416836 11.00000 0.02015 0.02286 = 0.01884 -0.00093 0.00680 0.00033 AFIX 23 H93A 2 0.408451 0.898727 0.460790 11.00000 -1.20000 H93B 2 0.551719 0.845872 0.518426 11.00000 -1.20000 AFIX 0 C94 1 0.419573 0.735634 0.346433 11.00000 0.01886 0.01959 = 0.02065 0.00073 0.00456 -0.00232 AFIX 23 H94A 2 0.485263 0.691537 0.309096 11.00000 -1.20000 H94B 2 0.401619 0.689179 0.441778 11.00000 -1.20000 AFIX 0 O95 4 0.304211 0.745410 0.200518 11.00000 0.01963 0.03058 = 0.02446 -0.00046 -0.00053 -0.00534 AFIX 147 H95 2 0.240586 0.751250 0.237827 11.00000 -1.20000 HKLF 4 REM mt27-37trans in P2(1)/c REM R1 = 0.0563 for 1214 Fo > 4sig(Fo) and 0.0850 for all 1723 data REM 156 parameters refined using 3 restraints END ; _[local]_cod_data_source_file gp5052.cif _[local]_cod_data_source_block VI _[local]_cod_cif_authors_sg_H-M 'P 21/c' _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_cell_volume 923.30(15) _cod_database_code 2105164 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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 0.9389(2) 0.62257(19) 0.6574(3) 0.0176(5) Uani d D 1 1 H H1 0.989(3) 0.565(2) 0.717(4) 0.021 Uiso d D 1 1 C C2 0.8285(3) 0.5945(2) 0.5242(4) 0.0171(5) Uani d . 1 1 N N3 0.7498(2) 0.6754(2) 0.4241(3) 0.0179(5) Uani d . 1 1 C C4 0.7903(3) 0.7886(2) 0.4713(4) 0.0167(6) Uani d . 1 1 C C5 0.8981(2) 0.8258(2) 0.6046(4) 0.0168(5) Uani d . 1 1 C C6 0.9832(3) 0.7382(2) 0.7059(4) 0.0168(6) Uani d . 1 1 N N7 0.9048(2) 0.95018(19) 0.6117(3) 0.0193(5) Uani d . 1 1 C C8 0.8037(3) 0.9860(2) 0.4840(4) 0.0182(6) Uani d . 1 1 H H8 0.7831 1.0679 0.4568 0.022 Uiso calc R 1 1 N N9 0.7299(2) 0.8920(2) 0.3929(3) 0.0180(5) Uani d . 1 1 N N21 0.7989(2) 0.4779(2) 0.4990(3) 0.0228(5) Uani d D 1 1 H H21A 0.726(2) 0.460(3) 0.420(4) 0.027 Uiso d D 1 1 H H21B 0.851(3) 0.422(3) 0.561(4) 0.027 Uiso d D 1 1 O O61 1.08727(19) 0.75473(17) 0.8263(3) 0.0237(5) Uani d . 1 1 C C91 0.6116(3) 0.8976(2) 0.2434(4) 0.0178(5) Uani d . 1 1 H H91A 0.6242 0.9551 0.1557 0.021 Uiso calc R 1 1 H H91B 0.5951 0.8179 0.1865 0.021 Uiso calc R 1 1 O O92 0.50241(18) 0.93261(16) 0.2897(3) 0.0193(5) Uani d . 1 1 C C93 0.4725(3) 0.8573(2) 0.4169(4) 0.0206(6) Uani d . 1 1 H H93A 0.4084 0.8987 0.4609 0.025 Uiso calc R 1 1 H H93B 0.5517 0.8457 0.5185 0.025 Uiso calc R 1 1 C C94 0.4195(3) 0.7356(2) 0.3464(4) 0.0200(6) Uani d . 1 1 H H94A 0.4852 0.6915 0.3092 0.024 Uiso calc R 1 1 H H94B 0.4014 0.6892 0.4417 0.024 Uiso calc R 1 1 O O95 0.3043(2) 0.74536(19) 0.2006(3) 0.0268(5) Uani d . 1 1 H H95 0.2405 0.7501 0.2377 0.032 Uiso calc R 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 0.0152(11) 0.0138(11) 0.0216(12) 0.0001(8) 0.0027(9) 0.0005(8) C2 0.0160(12) 0.0167(12) 0.0202(14) 0.0017(10) 0.0080(11) -0.0019(10) N3 0.0189(11) 0.0152(11) 0.0190(11) -0.0006(9) 0.0053(9) -0.0011(8) C4 0.0170(12) 0.0173(12) 0.0172(13) 0.0011(10) 0.0075(11) 0.0025(10) C5 0.0153(12) 0.0142(12) 0.0203(13) -0.0038(10) 0.0046(11) -0.0019(10) C6 0.0160(13) 0.0156(12) 0.0183(14) -0.0001(9) 0.0047(11) 0.0007(9) N7 0.0193(11) 0.0130(11) 0.0244(12) -0.0021(9) 0.0051(10) -0.0007(9) C8 0.0184(13) 0.0116(11) 0.0248(14) -0.0006(10) 0.0069(11) 0.0014(10) N9 0.0194(11) 0.0142(10) 0.0198(12) 0.0015(9) 0.0055(10) 0.0016(8) N21 0.0237(12) 0.0136(11) 0.0256(13) -0.0004(10) -0.0002(10) -0.0006(9) O61 0.0197(10) 0.0190(10) 0.0274(11) -0.0020(7) 0.0000(9) 0.0002(8) C91 0.0185(12) 0.0181(12) 0.0164(13) 0.0019(10) 0.0048(11) 0.0026(10) O92 0.0176(9) 0.0156(9) 0.0234(11) 0.0018(7) 0.0047(8) 0.0021(7) C93 0.0210(13) 0.0230(14) 0.0185(14) 0.0003(11) 0.0071(11) -0.0009(10) C94 0.0198(13) 0.0193(13) 0.0200(14) -0.0024(10) 0.0049(11) 0.0006(10) O95 0.0209(10) 0.0308(11) 0.0236(11) -0.0053(9) -0.0002(9) -0.0004(8) 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 C6 124.9(2) C2 N1 H1 120(2) C6 N1 H1 115(2) N3 C2 N21 119.4(3) N3 C2 N1 123.8(2) N21 C2 N1 116.8(2) C2 N3 C4 112.0(2) N3 C4 N9 126.0(2) N3 C4 C5 128.4(2) N9 C4 C5 105.6(2) C4 C5 N7 110.7(2) C4 C5 C6 118.7(2) N7 C5 C6 130.6(3) O61 C6 N1 120.2(2) O61 C6 C5 127.7(2) N1 C6 C5 112.0(2) C8 N7 C5 104.7(2) N7 C8 N9 112.8(2) N7 C8 H8 123.6 N9 C8 H8 123.6 C4 N9 C8 106.3(2) C4 N9 C91 125.6(2) C8 N9 C91 128.1(2) C2 N21 H21A 117(2) C2 N21 H21B 121(2) H21A N21 H21B 122(3) O92 C91 N9 113.7(2) O92 C91 H91A 108.8 N9 C91 H91A 108.8 O92 C91 H91B 108.8 N9 C91 H91B 108.8 H91A C91 H91B 107.7 C91 O92 C93 115.0(2) O92 C93 C94 114.2(2) O92 C93 H93A 108.7 C94 C93 H93A 108.7 O92 C93 H93B 108.7 C94 C93 H93B 108.7 H93A C93 H93B 107.6 O95 C94 C93 111.8(2) O95 C94 H94A 109.3 C93 C94 H94A 109.3 O95 C94 H94B 109.3 C93 C94 H94B 109.3 H94A C94 H94B 107.9 C94 O95 H95 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance N1 C2 1.369(4) N1 C6 1.390(3) N1 H1 0.885(18) C2 N3 1.327(4) C2 N21 1.342(4) N3 C4 1.353(4) C4 N9 1.378(3) C4 C5 1.379(4) C5 N7 1.391(4) C5 C6 1.414(4) C6 O61 1.250(3) N7 C8 1.307(4) C8 N9 1.383(4) C8 H8 0.9500 N9 C91 1.458(3) N21 H21A 0.864(19) N21 H21B 0.881(19) C91 O92 1.410(3) C91 H91A 0.9900 C91 H91B 0.9900 O92 C93 1.433(3) C93 C94 1.513(4) C93 H93A 0.9900 C93 H93B 0.9900 C94 O95 1.423(3) C94 H94A 0.9900 C94 H94B 0.9900 O95 H95 0.8400 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 N7 2_746 0.885(18) 1.960(19) 2.834(3) 169(3) N21 H21A O95 2_645 0.864(19) 2.56(3) 3.069(3) 118(3) N21 H21B O61 2_746 0.881(19) 2.09(2) 2.934(3) 159(3) O95 H95 O61 4_475 0.84 2.01 2.849(3) 174.8 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 N3 0.2(4) C6 N1 C2 N21 -178.3(2) N21 C2 N3 C4 177.3(2) N1 C2 N3 C4 -1.2(4) C2 N3 C4 N9 179.9(2) C2 N3 C4 C5 -0.1(4) N3 C4 C5 N7 -179.3(2) N9 C4 C5 N7 0.7(3) N3 C4 C5 C6 2.3(4) N9 C4 C5 C6 -177.7(2) C2 N1 C6 O61 -178.0(3) C2 N1 C6 C5 1.9(4) C4 C5 C6 O61 177.0(3) N7 C5 C6 O61 -1.1(5) C4 C5 C6 N1 -2.9(4) N7 C5 C6 N1 179.0(3) C4 C5 N7 C8 -0.6(3) C6 C5 N7 C8 177.6(3) C5 N7 C8 N9 0.2(3) N3 C4 N9 C8 179.5(2) C5 C4 N9 C8 -0.5(3) N3 C4 N9 C91 -0.6(4) C5 C4 N9 C91 179.4(2) N7 C8 N9 C4 0.2(3) N7 C8 N9 C91 -179.7(2) C4 N9 C91 O92 105.8(3) C8 N9 C91 O92 -74.3(3) N9 C91 O92 C93 -58.4(3) C91 O92 C93 C94 -71.4(3) O92 C93 C94 O95 -59.0(3)