#------------------------------------------------------------------------------ #$Date: 2012-09-06 14:55:08 +0100 (Thu, 06 Sep 2012) $ #$Revision: 65855 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/51/2105160.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_2105160 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 'C4 H4 F N3 O, C4 H6 N4 O, H2 O' _chemical_formula_sum 'C8 H12 F N7 O3' _chemical_formula_weight 273.25 _chemical_name_systematic ; ; ; _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 61.797(11) _cell_angle_beta 64.500(11) _cell_angle_gamma 67.138(11) _cell_formula_units_Z 2 _cell_length_a 8.3280(12) _cell_length_b 9.3484(14) _cell_length_c 9.4779(15) _cell_measurement_reflns_used 4119 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 25.83 _cell_measurement_theta_min 4.19 _cell_volume 570.83(17) _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 0.993 _diffrn_measured_fraction_theta_max 0.985 _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 0.0932 _diffrn_reflns_av_sigmaI/netI 0.0638 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 6264 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.64 _diffrn_reflns_theta_min 4.19 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.135 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.590 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 284 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _refine_diff_density_max 0.290 _refine_diff_density_min -0.280 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.964 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 212 _refine_ls_number_reflns 2124 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.964 _refine_ls_R_factor_all 0.0619 _refine_ls_R_factor_gt 0.0469 _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^)+(0.0752P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1134 _refine_ls_wR_factor_ref 0.1218 _reflns_number_gt 1615 _reflns_number_total 2124 _reflns_threshold_expression I>2\s(I) _iucr_refine_instructions_details ; TITL mt19-8 in P-1 CELL 0.71073 8.3280 9.3484 9.4779 61.797 64.500 67.138 ZERR 2.00 0.0012 0.0014 0.0015 0.011 0.011 0.011 LATT 1 SFAC C H F N O UNIT 16 24 2 14 6 REM farbloser Block SIZE 0.15 0.3 0.3 ACTA 50 L.S. 10 BOND $H CONF FMAP 2 PLAN 10 TEMP -100 EQIV_$1 x, y+1, z-1 EQIV_$2 -x+1, -y, -z+1 EQIV_$3 -x+2, -y+1, -z+1 EQIV_$4 x-1, y, z HTAB N3 N3' HTAB N61 O21'_$1 HTAB N21 O21'_$2 HTAB N21 O21' HTAB N1' O1W_$2 HTAB N41' O41 HTAB N41' O41_$3 HTAB O1W O41_$4 HTAB O1W N1 WGHT 0.075200 FVAR 1.17809 N1 4 0.454177 0.490582 0.218248 11.00000 0.01958 0.02483 = 0.02261 -0.00554 -0.00993 -0.00780 C2 1 0.531112 0.370695 0.335204 11.00000 0.01535 0.02254 = 0.02092 -0.00985 -0.00571 -0.00314 N3 4 0.652258 0.393926 0.380024 11.00000 0.01804 0.01679 = 0.02302 -0.00458 -0.01137 -0.00383 H3 2 0.710187 0.313412 0.449147 11.00000 0.02365 C4 1 0.701684 0.545481 0.308642 11.00000 0.01538 0.02005 = 0.02103 -0.01014 -0.00462 -0.00454 C5 1 0.617929 0.674275 0.189276 11.00000 0.02057 0.01910 = 0.02157 -0.00457 -0.00612 -0.00735 AFIX 43 H5 2 0.640663 0.782493 0.139390 11.00000 -1.20000 AFIX 0 C6 1 0.500285 0.641191 0.144598 11.00000 0.01828 0.02326 = 0.01861 -0.00656 -0.00555 -0.00338 N21 4 0.493932 0.220530 0.411958 11.00000 0.02868 0.02028 = 0.03408 -0.00369 -0.02007 -0.00834 H21A 2 0.418299 0.204602 0.378878 11.00000 0.03006 H21B 2 0.542866 0.147915 0.484734 11.00000 0.01837 O41 5 0.818373 0.551966 0.357029 11.00000 0.02393 0.02189 = 0.02992 -0.00788 -0.01367 -0.00765 N61 4 0.419497 0.758378 0.025514 11.00000 0.03265 0.02896 = 0.02780 0.00245 -0.01928 -0.01090 H61A 2 0.358950 0.726146 -0.009217 11.00000 0.04619 H61B 2 0.462410 0.845005 -0.043968 11.00000 0.05016 N1' 4 0.881616 -0.170767 0.790637 11.00000 0.02529 0.01644 = 0.02630 -0.00176 -0.01176 -0.00835 H1' 2 0.862712 -0.266993 0.816506 11.00000 0.03536 C2' 1 0.787901 -0.032714 0.688064 11.00000 0.02036 0.01876 = 0.02254 -0.00518 -0.00803 -0.00655 N3' 4 0.832646 0.116838 0.620664 11.00000 0.02066 0.01705 = 0.02334 -0.00440 -0.01080 -0.00571 C4' 1 0.959948 0.130754 0.661701 11.00000 0.01780 0.02003 = 0.02182 -0.00883 -0.00728 -0.00471 C5' 1 1.051275 -0.012420 0.773408 11.00000 0.02172 0.02505 = 0.02749 -0.00851 -0.01326 -0.00519 C6' 1 1.012989 -0.161183 0.834520 11.00000 0.02286 0.02009 = 0.02334 -0.00288 -0.01222 -0.00267 AFIX 43 H6' 2 1.075135 -0.257384 0.906278 11.00000 -1.20000 AFIX 0 O21' 5 0.663115 -0.048233 0.659767 11.00000 0.03248 0.02120 = 0.04215 -0.00245 -0.02330 -0.01180 N41' 4 0.999586 0.278567 0.596904 11.00000 0.02906 0.02016 = 0.03414 -0.00492 -0.01964 -0.00832 H41C 2 0.932411 0.361313 0.530946 11.00000 0.04014 H41D 2 1.087402 0.288338 0.623711 11.00000 0.04140 F51' 3 1.177361 0.008354 0.813223 11.00000 0.04082 0.03179 = 0.05058 -0.00493 -0.03550 -0.00992 O1W 5 0.166231 0.491372 0.128396 11.00000 0.02042 0.02475 = 0.02779 -0.00721 -0.00984 -0.00651 H1WA 2 0.063929 0.517336 0.201527 11.00000 0.03770 H1WB 2 0.251997 0.489231 0.162814 11.00000 0.03290 HKLF 4 REM mt19-8 in P-1 REM R1 = 0.0469 for 1615 Fo > 4sig(Fo) and 0.0619 for all 2124 data REM 212 parameters refined using 0 restraints END ; _[local]_cod_data_source_file gp5052.cif _[local]_cod_data_source_block Va _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 570.83(15) _cod_database_code 2105160 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 0.4542(2) 0.49058(18) 0.21825(19) 0.0214(3) Uani d . 1 1 C C2 0.5311(2) 0.3707(2) 0.3352(2) 0.0191(4) Uani d . 1 1 N N3 0.6523(2) 0.39393(18) 0.38002(19) 0.0186(3) Uani d . 1 1 H H3 0.710(3) 0.313(3) 0.449(3) 0.024(5) Uiso d . 1 1 C C4 0.7017(2) 0.5455(2) 0.3086(2) 0.0179(4) Uani d . 1 1 C C5 0.6179(2) 0.6743(2) 0.1893(2) 0.0209(4) Uani d . 1 1 H H5 0.6407 0.7825 0.1394 0.025 Uiso calc R 1 1 C C6 0.5003(2) 0.6412(2) 0.1446(2) 0.0211(4) Uani d . 1 1 N N21 0.4939(2) 0.2205(2) 0.4120(2) 0.0254(4) Uani d . 1 1 H H21A 0.418(3) 0.205(3) 0.379(3) 0.030(6) Uiso d . 1 1 H H21B 0.543(3) 0.148(3) 0.485(3) 0.018(5) Uiso d . 1 1 O O41 0.81837(17) 0.55197(15) 0.35703(16) 0.0230(3) Uani d . 1 1 N N61 0.4195(2) 0.7584(2) 0.0255(2) 0.0302(4) Uani d . 1 1 H H61A 0.359(4) 0.726(3) -0.009(3) 0.046(7) Uiso d . 1 1 H H61B 0.462(4) 0.845(4) -0.044(4) 0.050(7) Uiso d . 1 1 N N1' 0.8816(2) -0.17077(18) 0.79064(19) 0.0226(4) Uani d . 1 1 H H1' 0.863(3) -0.267(3) 0.817(3) 0.035(6) Uiso d . 1 1 C C2' 0.7879(2) -0.0327(2) 0.6881(2) 0.0203(4) Uani d . 1 1 N N3' 0.8326(2) 0.11684(17) 0.62066(19) 0.0196(3) Uani d . 1 1 C C4' 0.9599(2) 0.1308(2) 0.6617(2) 0.0188(4) Uani d . 1 1 C C5' 1.0513(2) -0.0124(2) 0.7734(2) 0.0231(4) Uani d . 1 1 C C6' 1.0130(2) -0.1612(2) 0.8345(2) 0.0231(4) Uani d . 1 1 H H6' 1.0751 -0.2574 0.9063 0.028 Uiso calc R 1 1 O O21' 0.66311(18) -0.04823(15) 0.65977(18) 0.0294(4) Uani d . 1 1 N N41' 0.9996(2) 0.2786(2) 0.5969(2) 0.0252(4) Uani d . 1 1 H H41C 0.932(3) 0.361(3) 0.531(3) 0.040(7) Uiso d . 1 1 H H41D 1.087(4) 0.288(3) 0.624(3) 0.041(6) Uiso d . 1 1 F F51' 1.17736(16) 0.00835(15) 0.81322(16) 0.0366(3) Uani d . 1 1 O O1W 0.16623(19) 0.49137(15) 0.12840(17) 0.0240(3) Uani d . 1 1 H H1WA 0.064(4) 0.517(3) 0.202(3) 0.038(6) Uiso d . 1 1 H H1WB 0.252(4) 0.489(3) 0.163(3) 0.033(6) Uiso 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 0.0196(7) 0.0248(8) 0.0226(8) -0.0078(6) -0.0099(6) -0.0055(6) C2 0.0153(8) 0.0225(9) 0.0209(9) -0.0031(6) -0.0057(7) -0.0098(7) N3 0.0180(7) 0.0168(8) 0.0230(8) -0.0038(6) -0.0114(7) -0.0046(6) C4 0.0154(8) 0.0200(9) 0.0210(9) -0.0045(6) -0.0046(7) -0.0101(7) C5 0.0206(9) 0.0191(9) 0.0216(9) -0.0073(7) -0.0061(7) -0.0046(7) C6 0.0183(9) 0.0233(9) 0.0186(9) -0.0034(7) -0.0056(7) -0.0066(7) N21 0.0287(9) 0.0203(8) 0.0341(9) -0.0083(7) -0.0201(8) -0.0037(7) O41 0.0239(7) 0.0219(7) 0.0299(7) -0.0076(5) -0.0137(6) -0.0079(6) N61 0.0327(9) 0.0290(9) 0.0278(9) -0.0109(7) -0.0193(8) 0.0024(7) N1' 0.0253(8) 0.0164(8) 0.0263(8) -0.0083(6) -0.0118(7) -0.0018(7) C2' 0.0204(9) 0.0188(9) 0.0225(9) -0.0065(7) -0.0080(7) -0.0052(7) N3' 0.0207(8) 0.0171(7) 0.0233(8) -0.0057(6) -0.0108(6) -0.0044(6) C4' 0.0178(8) 0.0200(8) 0.0218(9) -0.0047(6) -0.0073(7) -0.0088(7) C5' 0.0217(9) 0.0250(9) 0.0275(10) -0.0052(7) -0.0133(8) -0.0085(8) C6' 0.0229(9) 0.0201(9) 0.0233(9) -0.0027(7) -0.0122(8) -0.0029(7) O21' 0.0325(7) 0.0212(7) 0.0421(8) -0.0118(5) -0.0233(7) -0.0025(6) N41' 0.0291(9) 0.0202(8) 0.0341(9) -0.0083(7) -0.0196(8) -0.0049(7) F51' 0.0408(7) 0.0318(6) 0.0506(8) -0.0099(5) -0.0355(6) -0.0049(5) O1W 0.0204(7) 0.0247(7) 0.0278(7) -0.0065(5) -0.0098(6) -0.0072(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 116.85(15) N21 C2 N1 120.43(16) N21 C2 N3 117.18(16) N1 C2 N3 122.38(15) C2 N3 C4 122.42(15) C2 N3 H3 122.4(14) C4 N3 H3 115.0(14) O41 C4 N3 117.09(15) O41 C4 C5 126.95(15) N3 C4 C5 115.96(15) C6 C5 C4 118.91(15) C6 C5 H5 120.5 C4 C5 H5 120.5 N61 C6 N1 114.50(16) N61 C6 C5 122.10(16) N1 C6 C5 123.39(16) C2 N21 H21A 116.8(14) C2 N21 H21B 118.8(13) H21A N21 H21B 124(2) C6 N61 H61A 118.2(16) C6 N61 H61B 119.6(18) H61A N61 H61B 117(2) C6' N1' C2' 122.12(14) C6' N1' H1' 121.1(16) C2' N1' H1' 116.4(16) O21' C2' N3' 121.64(15) O21' C2' N1' 118.93(15) N3' C2' N1' 119.43(15) C4' N3' C2' 119.89(14) N41' C4' N3' 119.04(16) N41' C4' C5' 120.99(16) N3' C4' C5' 119.96(15) C6' C5' F51' 121.86(16) C6' C5' C4' 120.31(16) F51' C5' C4' 117.82(15) C5' C6' N1' 118.18(16) C5' C6' H6' 120.9 N1' C6' H6' 120.9 C4' N41' H41C 114.3(15) C4' N41' H41D 119.3(15) H41C N41' H41D 126(2) H1WA O1W H1WB 104(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance N1 C2 1.332(2) N1 C6 1.370(2) C2 N21 1.332(2) C2 N3 1.368(2) N3 C4 1.394(2) N3 H3 0.87(2) C4 O41 1.270(2) C4 C5 1.398(3) C5 C6 1.397(2) C5 H5 0.9500 C6 N61 1.356(2) N21 H21A 0.90(2) N21 H21B 0.83(2) N61 H61A 0.90(3) N61 H61B 0.86(3) N1' C6' 1.372(2) N1' C2' 1.380(2) N1' H1' 0.87(3) C2' O21' 1.252(2) C2' N3' 1.363(2) N3' C4' 1.342(2) C4' N41' 1.332(2) C4' C5' 1.433(3) C5' C6' 1.340(3) C5' F51' 1.3607(19) C6' H6' 0.9500 N41' H41C 0.90(3) N41' H41D 0.92(3) O1W H1WA 0.87(3) O1W H1WB 0.89(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 N3 H3 N3' . 0.87(2) 2.05(3) 2.917(2) 176(2) N61 H61B O21' 1_564 0.86(3) 2.51(3) 3.205(2) 139(2) N21 H21A O21' 2_656 0.90(2) 2.05(2) 2.864(2) 150(2) N21 H21B O21' . 0.83(2) 2.06(2) 2.887(2) 174.9(19) N1' H1' O1W 2_656 0.87(3) 1.99(3) 2.867(2) 177(2) N41' H41C O41 . 0.90(3) 2.01(3) 2.906(2) 171(2) N41' H41D O41 2_766 0.92(3) 2.04(3) 2.8441(19) 145(2) O1W H1WA O41 1_455 0.87(3) 1.95(3) 2.809(2) 170(2) O1W H1WB N1 . 0.89(3) 1.97(3) 2.8661(19) 175(2) 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 -179.64(16) C6 N1 C2 N3 -0.7(3) N21 C2 N3 C4 -179.93(16) N1 C2 N3 C4 1.1(3) C2 N3 C4 O41 -178.51(15) C2 N3 C4 C5 0.8(2) O41 C4 C5 C6 176.26(17) N3 C4 C5 C6 -3.0(2) C2 N1 C6 N61 179.47(16) C2 N1 C6 C5 -1.7(3) C4 C5 C6 N61 -177.61(17) C4 C5 C6 N1 3.6(3) C6' N1' C2' O21' -176.37(17) C6' N1' C2' N3' 3.4(3) O21' C2' N3' C4' 176.12(16) N1' C2' N3' C4' -3.6(3) C2' N3' C4' N41' -178.83(17) C2' N3' C4' C5' 1.3(3) N41' C4' C5' C6' -178.44(18) N3' C4' C5' C6' 1.4(3) N41' C4' C5' F51' 1.1(3) N3' C4' C5' F51' -179.07(15) F51' C5' C6' N1' 178.81(16) C4' C5' C6' N1' -1.7(3) C2' N1' C6' C5' -0.7(3)