# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2008 data_global _journal_coden_Cambridge 440 loop_ _publ_author_name 'Sally Price' 'Sarah Barnett' 'Ashley Hulme' 'Nizar Issa' 'Thomas Lewis' 'Louise Price' 'D Tocher' _publ_contact_author_name 'Sally Price' _publ_contact_author_email S.L.PRICE@UCL.AC.UK _publ_section_title ; A study of 5-substituted uracils ; # Attachment '5Uracils.cif' data_STR0526 _database_code_depnum_ccdc_archive 'CCDC 693298' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 5-Ethyluracil ; _chemical_name_common 'C6 H8 N2 O2' _chemical_melting_point ? _chemical_formula_moiety 'C6 H8 N2 O2' _chemical_formula_sum 'C6 H8 N2 O2' _chemical_formula_weight 140.14 _exptl_special_details ; The crystal was found to be a non-merohedral twin so GEMINI was used to index the data which showed that there were two, approximately equal components. The output p4p files for each component were read back into SMART and run through the BRAVAIS and L.S. routines. The data were combined to give a single p4p file and integrated simultaneously using SAINT+. The twin law was found to be 1 -0.01 -0.02/-0.00 1 0.01/0.25 -0.06 1. The dataset had 1731 data from component 1 only, 1711 data from component 2 only and 725 data belonging to both. I/s for overlapping reflections was 19.5. The dataset was corrected for absorption using TWINABS which was also used to produce an HKLF 4 file (non-overlapping reflections for component 1 only) for structure solution and refinement. The use of an HKLF 5 file, including refelections for both components, for refinement gave no improvement to the structure, parameters or data completeness. ; 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 3.9193(18) _cell_length_b 5.754(3) _cell_length_c 14.366(7) _cell_angle_alpha 100.027(7) _cell_angle_beta 96.109(7) _cell_angle_gamma 92.374(8) _cell_volume 316.6(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1243 _cell_measurement_theta_min 2.899 _cell_measurement_theta_max 28.178 _exptl_crystal_description Lath _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.470 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 148 _exptl_absorpt_coefficient_mu 0.113 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4518 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'TWINABS v1.02 (Bruker, 2003)' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 4168 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1026 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.90 _diffrn_reflns_theta_max 28.26 _reflns_number_total 1346 _reflns_number_gt 864 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART (Bruker 2001)' _computing_cell_refinement 'Bruker SAINT (Bruker 2003)' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL (Bruker 2001)' _computing_publication_material 'Bruker SHELXTL and local programs' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0676P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1346 _refine_ls_number_parameters 123 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0915 _refine_ls_R_factor_gt 0.0609 _refine_ls_wR_factor_ref 0.1453 _refine_ls_wR_factor_gt 0.1342 _refine_ls_goodness_of_fit_ref 0.931 _refine_ls_restrained_S_all 0.931 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O7 O 0.2403(4) 0.2531(3) 0.51027(9) 0.0288(5) Uani 1 1 d . . . O8 O 0.6523(4) 0.4227(3) 0.24431(9) 0.0284(5) Uani 1 1 d . . . N1 N 0.1263(5) -0.0155(3) 0.37250(11) 0.0231(5) Uani 1 1 d . . . H1 H 0.021(6) -0.109(5) 0.4092(14) 0.021(6) Uiso 1 1 d . . . N3 N 0.4385(5) 0.3324(4) 0.37510(12) 0.0235(5) Uani 1 1 d . . . H3 H 0.543(6) 0.465(5) 0.4122(16) 0.028(6) Uiso 1 1 d . . . C2 C 0.2668(6) 0.1930(4) 0.42413(13) 0.0212(5) Uani 1 1 d . . . C4 C 0.4867(6) 0.2824(4) 0.27908(14) 0.0206(5) Uani 1 1 d . . . C5 C 0.3271(6) 0.0557(4) 0.22770(13) 0.0190(5) Uani 1 1 d . . . C6 C 0.1585(6) -0.0832(4) 0.27646(13) 0.0203(5) Uani 1 1 d . . . H6 H 0.043(6) -0.244(4) 0.2478(13) 0.021(6) Uiso 1 1 d . . . C9 C 0.3640(7) -0.0065(4) 0.12336(13) 0.0218(5) Uani 1 1 d . . . H9A H 0.242(6) 0.104(5) 0.0904(14) 0.021(6) Uiso 1 1 d . . . H9B H 0.616(7) 0.021(4) 0.1161(14) 0.025(6) Uiso 1 1 d . . . C10 C 0.2440(7) -0.2591(5) 0.07761(15) 0.0257(6) Uani 1 1 d . . . H10A H -0.018(7) -0.283(5) 0.0819(14) 0.029(7) Uiso 1 1 d . . . H10B H 0.295(6) -0.286(4) 0.0143(16) 0.031(7) Uiso 1 1 d . . . H10C H 0.366(7) -0.371(5) 0.1138(17) 0.043(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O7 0.0422(11) 0.0220(10) 0.0199(8) -0.0002(6) 0.0057(6) -0.0125(8) O8 0.0382(11) 0.0204(10) 0.0274(8) 0.0072(6) 0.0071(6) -0.0086(8) N1 0.0331(12) 0.0167(12) 0.0190(9) 0.0031(7) 0.0045(7) -0.0064(9) N3 0.0323(12) 0.0155(12) 0.0206(9) -0.0006(7) 0.0024(7) -0.0067(9) C2 0.0246(13) 0.0167(14) 0.0212(10) 0.0019(8) 0.0012(8) -0.0024(10) C4 0.0213(13) 0.0178(13) 0.0231(10) 0.0057(8) 0.0012(8) 0.0003(10) C5 0.0209(13) 0.0160(13) 0.0191(10) 0.0022(8) 0.0004(8) 0.0000(9) C6 0.0232(13) 0.0141(13) 0.0220(10) 0.0019(8) -0.0008(8) -0.0028(10) C9 0.0256(14) 0.0200(14) 0.0197(10) 0.0046(8) 0.0020(8) -0.0022(10) C10 0.0322(16) 0.0227(14) 0.0200(10) -0.0016(8) 0.0046(9) -0.0050(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O7 C2 1.242(2) . ? O8 C4 1.220(3) . ? N1 C2 1.357(3) . ? N1 C6 1.388(3) . ? N1 H1 0.93(3) . ? N3 C2 1.358(3) . ? N3 C4 1.394(3) . ? N3 H3 0.90(3) . ? C4 C5 1.462(3) . ? C5 C6 1.347(3) . ? C5 C9 1.503(3) . ? C6 H6 1.01(2) . ? C9 C10 1.520(3) . ? C9 H9A 0.97(2) . ? C9 H9B 1.01(3) . ? C10 H10A 1.04(3) . ? C10 H10B 0.94(2) . ? C10 H10C 1.00(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C6 122.38(18) . . ? C2 N1 H1 112.9(14) . . ? C6 N1 H1 124.6(14) . . ? C2 N3 C4 127.0(2) . . ? C2 N3 H3 113.4(15) . . ? C4 N3 H3 119.4(15) . . ? O7 C2 N1 122.48(19) . . ? O7 C2 N3 122.1(2) . . ? N1 C2 N3 115.41(18) . . ? O8 C4 N3 120.2(2) . . ? O8 C4 C5 125.14(19) . . ? N3 C4 C5 114.70(19) . . ? C6 C5 C4 118.28(19) . . ? C6 C5 C9 124.5(2) . . ? C4 C5 C9 117.26(18) . . ? C5 C6 N1 122.2(2) . . ? C5 C6 H6 124.4(12) . . ? N1 C6 H6 113.4(12) . . ? C5 C9 C10 114.67(19) . . ? C5 C9 H9A 108.7(12) . . ? C10 C9 H9A 110.3(14) . . ? C5 C9 H9B 107.2(11) . . ? C10 C9 H9B 109.2(14) . . ? H9A C9 H9B 106.4(19) . . ? C9 C10 H10A 108.9(14) . . ? C9 C10 H10B 108.8(15) . . ? H10A C10 H10B 111.9(18) . . ? C9 C10 H10C 109.4(16) . . ? H10A C10 H10C 108(2) . . ? H10B C10 H10C 110(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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 N1 C2 O7 -179.47(19) . . . . ? C6 N1 C2 N3 0.7(3) . . . . ? C4 N3 C2 O7 179.4(2) . . . . ? C4 N3 C2 N1 -0.7(3) . . . . ? C2 N3 C4 O8 -178.8(2) . . . . ? C2 N3 C4 C5 1.0(3) . . . . ? O8 C4 C5 C6 178.4(2) . . . . ? N3 C4 C5 C6 -1.3(3) . . . . ? O8 C4 C5 C9 -1.4(3) . . . . ? N3 C4 C5 C9 178.86(19) . . . . ? C4 C5 C6 N1 1.4(3) . . . . ? C9 C5 C6 N1 -178.8(2) . . . . ? C2 N1 C6 C5 -1.1(3) . . . . ? C6 C5 C9 C10 -9.2(3) . . . . ? C4 C5 C9 C10 170.6(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O7 0.93(3) 1.89(3) 2.815(3) 170(2) 2_556 N3 H3 O7 0.90(3) 1.91(3) 2.815(3) 179(2) 2_666 _diffrn_measured_fraction_theta_max 0.856 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.938 _refine_diff_density_max 0.423 _refine_diff_density_min -0.313 _refine_diff_density_rms 0.077 #===END data_STR0521 _database_code_depnum_ccdc_archive 'CCDC 693299' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '5-Cyanouracil' ; _chemical_name_common 'C5 H3 N3 O2' _chemical_melting_point ? _chemical_formula_moiety 'C5 H3 N3 O2' _chemical_formula_sum 'C5 H3 N3 O2' _chemical_formula_weight 137.10 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n 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' _cell_length_a 9.0098(18) _cell_length_b 6.6035(13) _cell_length_c 9.1805(18) _cell_angle_alpha 90.00 _cell_angle_beta 98.124(3) _cell_angle_gamma 90.00 _cell_volume 540.72(19) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2223 _cell_measurement_theta_min 2.964 _cell_measurement_theta_max 28.063 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.29 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.684 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 280 _exptl_absorpt_coefficient_mu 0.136 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.856 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 4294 _diffrn_reflns_av_R_equivalents 0.0199 _diffrn_reflns_av_sigmaI/netI 0.0204 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 28.23 _reflns_number_total 1270 _reflns_number_gt 1146 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0746P)^2^+0.1140P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1270 _refine_ls_number_parameters 103 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0429 _refine_ls_R_factor_gt 0.0398 _refine_ls_wR_factor_ref 0.1121 _refine_ls_wR_factor_gt 0.1091 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O7 O 0.93843(9) 0.26038(13) 0.51199(10) 0.0225(2) Uani 1 1 d . . . O8 O 0.64102(10) 0.79752(12) 0.35913(10) 0.0224(3) Uani 1 1 d . . . N1 N 0.69620(11) 0.20066(14) 0.41799(11) 0.0178(3) Uani 1 1 d . . . H1 H 0.7121(19) 0.071(3) 0.4333(19) 0.032(4) Uiso 1 1 d . . . N3 N 0.78729(11) 0.52866(15) 0.43790(11) 0.0180(3) Uani 1 1 d . . . H3 H 0.861(2) 0.606(3) 0.4649(17) 0.029(4) Uiso 1 1 d . . . N9 N 0.28284(12) 0.60485(17) 0.20394(13) 0.0281(3) Uani 1 1 d . . . C2 C 0.81618(12) 0.32610(17) 0.45969(12) 0.0174(3) Uani 1 1 d . . . C4 C 0.65438(12) 0.61404(17) 0.37398(12) 0.0168(3) Uani 1 1 d . . . C5 C 0.53666(12) 0.46835(17) 0.32688(12) 0.0169(3) Uani 1 1 d . . . C6 C 0.56187(13) 0.26788(18) 0.35167(13) 0.0173(3) Uani 1 1 d . . . H6 H 0.4864(16) 0.169(3) 0.3235(16) 0.020(4) Uiso 1 1 d . . . C9 C 0.39504(13) 0.54349(18) 0.25702(13) 0.0200(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O7 0.0153(4) 0.0172(4) 0.0327(5) 0.0048(3) -0.0041(3) -0.0017(3) O8 0.0238(5) 0.0119(4) 0.0297(5) -0.0002(3) -0.0021(4) -0.0006(3) N1 0.0153(5) 0.0109(5) 0.0261(5) 0.0008(3) -0.0015(4) -0.0013(3) N3 0.0152(5) 0.0129(5) 0.0244(5) -0.0001(4) -0.0020(4) -0.0036(4) N9 0.0219(5) 0.0246(6) 0.0366(6) -0.0007(5) -0.0005(4) 0.0040(4) C2 0.0156(5) 0.0152(5) 0.0205(5) 0.0005(4) 0.0001(4) -0.0019(4) C4 0.0166(5) 0.0148(5) 0.0182(5) -0.0007(4) 0.0004(4) -0.0002(4) C5 0.0139(5) 0.0159(5) 0.0201(5) -0.0016(4) -0.0005(4) -0.0003(4) C6 0.0139(5) 0.0162(6) 0.0212(5) -0.0013(4) 0.0007(4) -0.0026(4) C9 0.0185(6) 0.0169(5) 0.0247(6) -0.0027(4) 0.0030(4) -0.0027(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O7 C2 1.2176(14) . ? O8 C4 1.2233(15) . ? N1 C6 1.3507(15) . ? N1 C2 1.3726(15) . ? N1 H1 0.88(2) . ? N3 C2 1.3719(15) . ? N3 C4 1.3775(14) . ? N3 H3 0.848(19) . ? N9 C9 1.1332(16) . ? C4 C5 1.4519(15) . ? C5 C6 1.3569(16) . ? C5 C9 1.4333(16) . ? C6 H6 0.953(16) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 N1 C2 123.20(10) . . ? C6 N1 H1 120.6(12) . . ? C2 N1 H1 116.2(12) . . ? C2 N3 C4 126.64(10) . . ? C2 N3 H3 115.0(12) . . ? C4 N3 H3 118.3(12) . . ? O7 C2 N3 123.19(11) . . ? O7 C2 N1 121.85(11) . . ? N3 C2 N1 114.96(10) . . ? O8 C4 N3 121.25(10) . . ? O8 C4 C5 124.53(11) . . ? N3 C4 C5 114.22(10) . . ? C6 C5 C9 122.02(10) . . ? C6 C5 C4 119.90(10) . . ? C9 C5 C4 118.07(11) . . ? N1 C6 C5 120.95(10) . . ? N1 C6 H6 117.2(10) . . ? C5 C6 H6 121.9(10) . . ? N9 C9 C5 178.79(13) . . ? 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 N3 C2 O7 177.09(10) . . . . ? C4 N3 C2 N1 -2.93(17) . . . . ? C6 N1 C2 O7 -175.92(11) . . . . ? C6 N1 C2 N3 4.10(17) . . . . ? C2 N3 C4 O8 -179.56(10) . . . . ? C2 N3 C4 C5 0.00(16) . . . . ? O8 C4 C5 C6 -178.43(11) . . . . ? N3 C4 C5 C6 2.02(15) . . . . ? O8 C4 C5 C9 0.51(17) . . . . ? N3 C4 C5 C9 -179.04(9) . . . . ? C2 N1 C6 C5 -2.31(18) . . . . ? C9 C5 C6 N1 -179.86(10) . . . . ? C4 C5 C6 N1 -0.96(17) . . . . ? C6 C5 C9 N9 120(6) . . . . ? C4 C5 C9 N9 -59(6) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O8 0.88(2) 2.00(2) 2.7478(14) 142.1(16) 1_545 N3 H3 O7 0.848(19) 1.994(19) 2.8174(14) 163.4(16) 3_766 _diffrn_measured_fraction_theta_max 0.956 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.364 _refine_diff_density_min -0.237 _refine_diff_density_rms 0.065 #===END data_STR0481 _database_code_depnum_ccdc_archive 'CCDC 693300' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 5-Fluorouracil Benzonitrile solvate (1/1) ; _chemical_name_common 'C4 H3 F N2 O2, C7 H5 N' _chemical_melting_point ? _chemical_formula_moiety 'C11 H8 F N3 O2' _chemical_formula_sum 'C11 H8 F N3 O2' _chemical_formula_weight 233.20 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c 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' _cell_length_a 7.0460(7) _cell_length_b 24.035(2) _cell_length_c 6.8640(7) _cell_angle_alpha 90.00 _cell_angle_beta 116.554(2) _cell_angle_gamma 90.00 _cell_volume 1039.80(17) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3207 _cell_measurement_theta_min 3.232 _cell_measurement_theta_max 28.313 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.61 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.490 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 0.118 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9312 _exptl_absorpt_correction_T_max 0.9762 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 6296 _diffrn_reflns_av_R_equivalents 0.0158 _diffrn_reflns_av_sigmaI/netI 0.0202 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.34 _diffrn_reflns_theta_max 28.32 _reflns_number_total 2458 _reflns_number_gt 2120 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0704P)^2^+0.1044P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2458 _refine_ls_number_parameters 186 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0418 _refine_ls_R_factor_gt 0.0366 _refine_ls_wR_factor_ref 0.1119 _refine_ls_wR_factor_gt 0.1069 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F9 F 0.77370(11) 0.53530(2) 0.47672(10) 0.0349(2) Uani 1 1 d . . . O7 O 0.78333(11) 0.75765(3) 0.48646(11) 0.02615(19) Uani 1 1 d . . . O8 O 0.73777(12) 0.59562(3) 0.80378(12) 0.0308(2) Uani 1 1 d . . . N1 N 0.76448(12) 0.67589(3) 0.64341(12) 0.0218(2) Uani 1 1 d . . . H1 H 0.759(2) 0.6962(5) 0.751(2) 0.036(3) Uiso 1 1 d . . . N3 N 0.79340(13) 0.67649(3) 0.32191(13) 0.0223(2) Uani 1 1 d . . . H3 H 0.796(2) 0.6958(6) 0.218(2) 0.039(3) Uiso 1 1 d . . . C2 C 0.78097(14) 0.70615(4) 0.48336(14) 0.0206(2) Uani 1 1 d . . . C4 C 0.75762(14) 0.61849(4) 0.65631(15) 0.0226(2) Uani 1 1 d . . . C5 C 0.77613(15) 0.59107(4) 0.47709(16) 0.0233(2) Uani 1 1 d . . . C6 C 0.79034(15) 0.61946(4) 0.31721(15) 0.0230(2) Uani 1 1 d . . . H6 H 0.7998(19) 0.6025(5) 0.198(2) 0.030(3) Uiso 1 1 d . . . N11 N 0.71433(17) 0.23621(4) 0.95317(16) 0.0375(2) Uani 1 1 d . . . C11 C 0.72695(15) 0.34357(4) 0.95204(17) 0.0252(2) Uani 1 1 d . . . C12 C 0.76018(16) 0.37083(4) 0.79062(18) 0.0297(2) Uani 1 1 d . . . H12 H 0.779(2) 0.3494(5) 0.685(2) 0.041(4) Uiso 1 1 d . . . C13 C 0.76378(17) 0.42835(5) 0.7890(2) 0.0363(3) Uani 1 1 d . . . H13 H 0.789(2) 0.4479(7) 0.680(3) 0.051(4) Uiso 1 1 d . . . C14 C 0.73406(18) 0.45843(4) 0.9455(2) 0.0387(3) Uani 1 1 d . . . H14 H 0.738(2) 0.4987(7) 0.944(3) 0.048(4) Uiso 1 1 d . . . C15 C 0.69878(18) 0.43105(5) 1.1035(2) 0.0368(3) Uani 1 1 d . . . H15 H 0.675(2) 0.4524(6) 1.209(2) 0.046(4) Uiso 1 1 d . . . C16 C 0.69532(17) 0.37350(4) 1.10891(18) 0.0303(2) Uani 1 1 d . . . H16 H 0.668(2) 0.3539(5) 1.218(2) 0.034(3) Uiso 1 1 d . . . C17 C 0.72082(16) 0.28367(4) 0.95373(17) 0.0275(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F9 0.0577(4) 0.0159(3) 0.0345(4) -0.0001(2) 0.0235(3) 0.0006(2) O7 0.0430(4) 0.0182(3) 0.0222(4) -0.0001(2) 0.0190(3) -0.0005(3) O8 0.0465(4) 0.0242(4) 0.0278(4) 0.0058(3) 0.0220(3) 0.0003(3) N1 0.0321(4) 0.0183(4) 0.0187(4) -0.0001(3) 0.0145(3) 0.0010(3) N3 0.0321(4) 0.0193(4) 0.0193(4) -0.0005(3) 0.0150(3) -0.0014(3) C2 0.0251(4) 0.0193(4) 0.0184(4) 0.0003(3) 0.0106(4) -0.0005(3) C4 0.0259(5) 0.0202(5) 0.0220(5) 0.0020(3) 0.0109(4) 0.0005(3) C5 0.0293(5) 0.0158(4) 0.0246(5) -0.0009(3) 0.0118(4) 0.0006(3) C6 0.0275(5) 0.0208(5) 0.0218(5) -0.0028(3) 0.0119(4) -0.0001(3) N11 0.0556(6) 0.0236(5) 0.0387(5) 0.0010(4) 0.0259(5) 0.0008(4) C11 0.0245(4) 0.0206(5) 0.0282(5) -0.0007(4) 0.0096(4) 0.0001(3) C12 0.0305(5) 0.0266(5) 0.0335(6) 0.0009(4) 0.0156(4) -0.0001(4) C13 0.0357(6) 0.0283(6) 0.0452(7) 0.0086(5) 0.0182(5) -0.0010(4) C14 0.0355(6) 0.0184(5) 0.0548(7) -0.0006(4) 0.0136(5) -0.0004(4) C15 0.0376(6) 0.0281(6) 0.0402(6) -0.0092(4) 0.0134(5) 0.0021(4) C16 0.0325(5) 0.0277(5) 0.0291(5) -0.0015(4) 0.0122(4) 0.0011(4) C17 0.0324(5) 0.0253(5) 0.0263(5) 0.0008(4) 0.0145(4) 0.0013(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F9 C5 1.3405(10) . ? O7 C2 1.2378(11) . ? O8 C4 1.2137(12) . ? N1 C2 1.3651(12) . ? N1 C4 1.3846(12) . ? N1 H1 0.899(15) . ? N3 C2 1.3531(12) . ? N3 C6 1.3708(12) . ? N3 H3 0.859(15) . ? C4 C5 1.4520(13) . ? C5 C6 1.3336(14) . ? C6 H6 0.945(14) . ? N11 C17 1.1417(14) . ? C11 C16 1.3932(15) . ? C11 C12 1.3941(15) . ? C11 C17 1.4406(14) . ? C12 C13 1.3830(16) . ? C12 H12 0.947(15) . ? C13 C14 1.3861(18) . ? C13 H13 0.963(17) . ? C14 C15 1.3827(19) . ? C14 H14 0.969(16) . ? C15 C16 1.3844(15) . ? C15 H15 0.964(15) . ? C16 H16 0.975(14) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C4 126.90(8) . . ? C2 N1 H1 115.0(8) . . ? C4 N1 H1 118.1(8) . . ? C2 N3 C6 122.68(8) . . ? C2 N3 H3 115.4(9) . . ? C6 N3 H3 121.8(9) . . ? O7 C2 N3 122.39(8) . . ? O7 C2 N1 121.62(8) . . ? N3 C2 N1 115.99(8) . . ? O8 C4 N1 121.67(9) . . ? O8 C4 C5 126.05(9) . . ? N1 C4 C5 112.28(8) . . ? C6 C5 F9 121.05(8) . . ? C6 C5 C4 122.22(9) . . ? F9 C5 C4 116.72(8) . . ? C5 C6 N3 119.90(8) . . ? C5 C6 H6 123.6(7) . . ? N3 C6 H6 116.5(7) . . ? C16 C11 C12 120.89(10) . . ? C16 C11 C17 119.60(9) . . ? C12 C11 C17 119.49(9) . . ? C13 C12 C11 119.09(10) . . ? C13 C12 H12 121.9(8) . . ? C11 C12 H12 119.0(8) . . ? C12 C13 C14 120.37(11) . . ? C12 C13 H13 120.3(9) . . ? C14 C13 H13 119.3(9) . . ? C15 C14 C13 120.14(10) . . ? C15 C14 H14 120.1(9) . . ? C13 C14 H14 119.8(9) . . ? C14 C15 C16 120.53(11) . . ? C14 C15 H15 119.5(9) . . ? C16 C15 H15 120.0(9) . . ? C15 C16 C11 118.97(10) . . ? C15 C16 H16 120.9(7) . . ? C11 C16 H16 120.1(7) . . ? N11 C17 C11 179.35(12) . . ? 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 N3 C2 O7 -179.83(8) . . . . ? C6 N3 C2 N1 -0.15(12) . . . . ? C4 N1 C2 O7 179.16(8) . . . . ? C4 N1 C2 N3 -0.53(13) . . . . ? C2 N1 C4 O8 -178.27(9) . . . . ? C2 N1 C4 C5 1.60(13) . . . . ? O8 C4 C5 C6 177.68(10) . . . . ? N1 C4 C5 C6 -2.19(13) . . . . ? O8 C4 C5 F9 -0.91(14) . . . . ? N1 C4 C5 F9 179.23(7) . . . . ? F9 C5 C6 N3 -179.73(8) . . . . ? C4 C5 C6 N3 1.75(14) . . . . ? C2 N3 C6 C5 -0.49(14) . . . . ? C16 C11 C12 C13 0.70(15) . . . . ? C17 C11 C12 C13 179.38(9) . . . . ? C11 C12 C13 C14 -0.20(16) . . . . ? C12 C13 C14 C15 -0.54(18) . . . . ? C13 C14 C15 C16 0.79(18) . . . . ? C14 C15 C16 C11 -0.30(17) . . . . ? C12 C11 C16 C15 -0.45(16) . . . . ? C17 C11 C16 C15 -179.13(9) . . . . ? #C16 C11 C17 N11 117(10) . . . . ? #C12 C11 C17 N11 -61(10) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O7 0.899(15) 1.905(15) 2.7991(10) 172.7(12) 4_576 N3 H3 O7 0.859(15) 1.912(15) 2.7689(10) 175.4(13) 4_575 _diffrn_measured_fraction_theta_max 0.948 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.274 _refine_diff_density_min -0.236 _refine_diff_density_rms 0.054 #===END data_STR0469 _database_code_depnum_ccdc_archive 'CCDC 693301' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 5-Fluorouracil Formaide solvate (1/1) ; _chemical_name_common 'C4 H3 F N2 O2 , C H3 N O' _chemical_melting_point ? _chemical_formula_moiety 'C5 H6 F N3 O3 ' _chemical_formula_sum 'C5 H6 F N3 O3 ' _chemical_formula_weight 175.13 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' _cell_length_a 6.827(4) _cell_length_b 6.111(3) _cell_length_c 8.424(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.313(8) _cell_angle_gamma 90.00 _cell_volume 351.4(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1298 _cell_measurement_theta_min 2.418 _cell_measurement_theta_max 27.6775 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.655 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 180 _exptl_absorpt_coefficient_mu 0.153 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9512 _exptl_absorpt_correction_T_max 0.9774 _exptl_absorpt_process_details 'SADABS, (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 2892 _diffrn_reflns_av_R_equivalents 0.0243 _diffrn_reflns_av_sigmaI/netI 0.0242 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 28.28 _reflns_number_total 866 _reflns_number_gt 765 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0597P)^2^+0.1250P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 866 _refine_ls_number_parameters 92 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0476 _refine_ls_R_factor_gt 0.0407 _refine_ls_wR_factor_ref 0.1108 _refine_ls_wR_factor_gt 0.1061 _refine_ls_goodness_of_fit_ref 1.096 _refine_ls_restrained_S_all 1.096 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F9 F 0.5170(3) 0.7500 1.0024(2) 0.0290(4) Uani 1 2 d S . . O7 O 0.4985(4) 0.7500 0.3673(2) 0.0227(5) Uani 1 2 d S . . O8 O 0.1658(3) 0.7500 0.8306(3) 0.0288(6) Uani 1 2 d S . . N1 N 0.6732(4) 0.7500 0.5987(4) 0.0200(6) Uani 1 2 d S . . H1 H 0.795(7) 0.7500 0.534(6) 0.033(11) Uiso 1 2 d S . . N3 N 0.3351(5) 0.7500 0.6013(4) 0.0207(7) Uani 1 2 d S . . H3 H 0.232(7) 0.7500 0.550(5) 0.022(10) Uiso 1 2 d S . . C2 C 0.5035(6) 0.7500 0.5130(3) 0.0190(5) Uani 1 2 d S . . C4 C 0.3251(5) 0.7500 0.7636(4) 0.0187(7) Uani 1 2 d S . . C5 C 0.5138(5) 0.7500 0.8421(3) 0.0200(6) Uani 1 2 d S . . C6 C 0.6806(5) 0.7500 0.7613(4) 0.0211(7) Uani 1 2 d S . . H6 H 0.801(6) 0.7500 0.813(4) 0.014(9) Uiso 1 2 d S . . O10 O -0.0052(5) 0.7500 0.4125(2) 0.0325(5) Uani 1 2 d S . . C11 C -0.0150(5) 0.7500 0.2654(3) 0.0224(6) Uani 1 2 d S . . H11 H -0.139(6) 0.7500 0.206(5) 0.020(9) Uiso 1 2 d S . . N12 N 0.1408(5) 0.7500 0.1755(4) 0.0255(6) Uani 1 2 d S . . H12A H 0.126(6) 0.7500 0.083(5) 0.028(11) Uiso 1 2 d S . . H12B H 0.260(7) 0.7500 0.215(5) 0.047(13) Uiso 1 2 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F9 0.0293(10) 0.0424(8) 0.0153(7) 0.000 0.0013(9) 0.000 O7 0.0227(11) 0.0293(9) 0.0163(9) 0.000 0.0057(11) 0.000 O8 0.0207(11) 0.0428(13) 0.0230(12) 0.000 0.0039(10) 0.000 N1 0.0158(13) 0.0235(13) 0.0207(16) 0.000 0.0047(11) 0.000 N3 0.0186(16) 0.0246(13) 0.0189(14) 0.000 0.0013(11) 0.000 C2 0.0204(13) 0.0152(10) 0.0216(12) 0.000 0.0065(17) 0.000 C4 0.0222(17) 0.0185(13) 0.0156(15) 0.000 0.0046(12) 0.000 C5 0.0220(15) 0.0237(11) 0.0144(11) 0.000 -0.0003(16) 0.000 C6 0.0199(16) 0.0219(14) 0.0213(17) 0.000 -0.0024(13) 0.000 O10 0.0201(11) 0.0584(14) 0.0192(10) 0.000 0.0048(11) 0.000 C11 0.0211(15) 0.0261(12) 0.0200(13) 0.000 0.0024(15) 0.000 N12 0.0274(13) 0.0331(13) 0.0161(14) 0.000 0.0007(13) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F9 C5 1.351(3) . ? O7 C2 1.228(3) . ? O8 C4 1.228(5) . ? N1 C2 1.361(5) . ? N1 C6 1.371(4) . ? N1 H1 1.00(5) . ? N3 C4 1.370(4) . ? N3 C2 1.373(5) . ? N3 H3 0.82(5) . ? C4 C5 1.445(6) . ? C5 C6 1.330(5) . ? C6 H6 0.93(4) . ? O10 C11 1.241(3) . ? C11 N12 1.309(5) . ? C11 H11 0.98(4) . ? N12 H12A 0.79(4) . ? N12 H12B 0.88(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C6 123.8(3) . . ? C2 N1 H1 115(3) . . ? C6 N1 H1 121(3) . . ? C4 N3 C2 126.0(4) . . ? C4 N3 H3 118(3) . . ? C2 N3 H3 116(3) . . ? O7 C2 N1 123.3(3) . . ? O7 C2 N3 121.5(4) . . ? N1 C2 N3 115.2(2) . . ? O8 C4 N3 120.5(4) . . ? O8 C4 C5 125.4(3) . . ? N3 C4 C5 114.0(3) . . ? C6 C5 F9 120.2(3) . . ? C6 C5 C4 122.0(3) . . ? F9 C5 C4 117.8(3) . . ? C5 C6 N1 119.0(4) . . ? C5 C6 H6 121(2) . . ? N1 C6 H6 120(2) . . ? O10 C11 N12 122.6(4) . . ? O10 C11 H11 124(2) . . ? N12 C11 H11 114(2) . . ? C11 N12 H12A 118(3) . . ? C11 N12 H12B 122(3) . . ? H12A N12 H12B 119(5) . . ? 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 N1 C2 O7 180.0 . . . . ? C6 N1 C2 N3 0.0 . . . . ? C4 N3 C2 O7 180.0 . . . . ? C4 N3 C2 N1 0.000(1) . . . . ? C2 N3 C4 O8 180.0 . . . . ? C2 N3 C4 C5 0.000(1) . . . . ? O8 C4 C5 C6 180.000(1) . . . . ? N3 C4 C5 C6 0.000(1) . . . . ? O8 C4 C5 F9 0.000(1) . . . . ? N3 C4 C5 F9 180.0 . . . . ? F9 C5 C6 N1 180.000(1) . . . . ? C4 C5 C6 N1 0.000(1) . . . . ? C2 N1 C6 C5 0.000(1) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H3 O10 0.82(5) 1.99(5) 2.808(5) 176(4) . N1 H1 O10 1.00(5) 1.71(5) 2.705(4) 176(4) 1_655 N12 H12B O7 0.88(5) 2.06(5) 2.921(4) 164(4) . N12 H12A O8 0.79(4) 2.14(4) 2.911(4) 166(4) 1_554 _diffrn_measured_fraction_theta_max 0.909 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.433 _refine_diff_density_min -0.283 _refine_diff_density_rms 0.053 #===END data_STR0454 _database_code_depnum_ccdc_archive 'CCDC 693302' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 5-Chlorouracil ; _chemical_name_common 'C4 H3 Cl N2 O2' _chemical_melting_point ? _chemical_formula_moiety 'C4 H3 Cl N2 O2' _chemical_formula_sum 'C4 H3 Cl N2 O2' _chemical_formula_weight 146.53 _exptl_special_details ; The 5-chlorouracil was found to exhibit complete molecule disorder about the C5-Cl9 axis. The disorder was modelled anisotropically over two sites for all of the atoms with occupancy ratios of 85:15. The minor component was restrained to be flat and geometrically similar to the major component. Suitable restraints were also applied to the thermal parameters of the minor component (SIMU DELU EADP). The hydrogen atoms were geometrically placed on all atoms as necessary within the part instructions. ; 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n 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' _cell_length_a 8.4393(10) _cell_length_b 6.8412(8) _cell_length_c 9.3679(12) _cell_angle_alpha 90.00 _cell_angle_beta 104.201(2) _cell_angle_gamma 90.00 _cell_volume 524.33(11) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2448 _cell_measurement_theta_min 2.914 _cell_measurement_theta_max 28.231 _exptl_crystal_description Plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.856 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 296 _exptl_absorpt_coefficient_mu 0.633 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8632 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS v2.03' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 4328 _diffrn_reflns_av_R_equivalents 0.0163 _diffrn_reflns_av_sigmaI/netI 0.0215 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.91 _diffrn_reflns_theta_max 28.23 _reflns_number_total 1234 _reflns_number_gt 1131 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0583P)^2^+0.1791P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1234 _refine_ls_number_parameters 109 _refine_ls_number_restraints 96 _refine_ls_R_factor_all 0.0350 _refine_ls_R_factor_gt 0.0330 _refine_ls_wR_factor_ref 0.0941 _refine_ls_wR_factor_gt 0.0920 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl9 Cl 0.68025(18) 0.26631(16) 0.20136(16) 0.01884(19) Uani 0.85 1 d PD A 1 O7 O -0.0203(5) 0.2500(15) -0.0066(8) 0.0192(5) Uani 0.85 1 d PD A 1 O8 O 0.45461(13) -0.09015(15) 0.15376(12) 0.0182(3) Uani 0.85 1 d PD A 1 N1 N 0.2168(5) 0.4228(8) 0.0655(4) 0.0156(4) Uani 0.85 1 d PD A 1 H1 H 0.1639 0.5346 0.0489 0.019 Uiso 0.85 1 calc PR A 1 N3 N 0.2189(5) 0.0848(7) 0.0766(6) 0.0154(5) Uani 0.85 1 d PD A 1 H3 H 0.1632 -0.0253 0.0660 0.018 Uiso 0.85 1 calc PR A 1 C2 C 0.1304(5) 0.2538(8) 0.0423(6) 0.0148(4) Uani 0.85 1 d PD A 1 C4 C 0.3883(6) 0.0699(7) 0.1268(5) 0.0156(4) Uani 0.85 1 d PD A 1 C5 C 0.4705(4) 0.2593(6) 0.1432(3) 0.0151(3) Uani 0.85 1 d PD A 1 C6 C 0.3839(5) 0.4255(5) 0.1141(3) 0.0151(4) Uani 0.85 1 d PD A 1 H6 H 0.4395 0.5474 0.1275 0.018 Uiso 0.85 1 calc PR A 1 Cl9' Cl 0.6836(12) 0.2376(12) 0.2138(11) 0.01884(19) Uani 0.15 1 d PDU B 2 O7' O -0.015(3) 0.239(9) -0.004(4) 0.0192(5) Uani 0.15 1 d PDU B 2 O8' O 0.4488(7) 0.5987(9) 0.1514(7) 0.0182(3) Uani 0.15 1 d PDU B 2 N1' N 0.227(3) 0.074(4) 0.066(4) 0.0156(4) Uani 0.15 1 d PDU B 2 H1' H 0.1762 -0.0385 0.0467 0.019 Uiso 0.15 1 calc PR B 2 N3' N 0.218(3) 0.413(5) 0.074(2) 0.0154(5) Uani 0.15 1 d PDU B 2 H3' H 0.1596 0.5209 0.0587 0.018 Uiso 0.15 1 calc PR B 2 C2' C 0.137(3) 0.238(5) 0.043(3) 0.0148(4) Uani 0.15 1 d PDU B 2 C4' C 0.388(3) 0.434(3) 0.1275(14) 0.0156(4) Uani 0.15 1 d PDU B 2 C5' C 0.473(2) 0.246(3) 0.1483(15) 0.0151(3) Uani 0.15 1 d PDU B 2 C6' C 0.394(3) 0.073(4) 0.118(3) 0.0151(4) Uani 0.15 1 d PDU B 2 H6' H 0.4526 -0.0466 0.1330 0.018 Uiso 0.15 1 calc PR B 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl9 0.0129(2) 0.0171(4) 0.0250(4) 0.0038(3) 0.0017(2) -0.0001(3) O7 0.0135(6) 0.0122(14) 0.0304(6) -0.0002(6) 0.0026(5) 0.0003(5) O8 0.0150(5) 0.0126(5) 0.0258(6) 0.0020(4) 0.0026(4) 0.0027(3) N1 0.0140(6) 0.0088(8) 0.0236(10) 0.0009(7) 0.0041(6) 0.0003(5) N3 0.0140(8) 0.0088(8) 0.0232(13) 0.0005(7) 0.0042(7) 0.0007(6) C2 0.0151(7) 0.0110(11) 0.0185(6) 0.0000(6) 0.0041(6) 0.0010(5) C4 0.0149(8) 0.0146(6) 0.0177(10) -0.0004(7) 0.0047(6) 0.0008(5) C5 0.0129(6) 0.0134(8) 0.0188(7) 0.0005(4) 0.0035(5) -0.0006(4) C6 0.0147(6) 0.0134(7) 0.0171(9) -0.0003(6) 0.0038(7) -0.0022(5) Cl9' 0.0129(2) 0.0171(4) 0.0250(4) 0.0038(3) 0.0017(2) -0.0001(3) O7' 0.0135(6) 0.0122(14) 0.0304(6) -0.0002(6) 0.0026(5) 0.0003(5) O8' 0.0150(5) 0.0126(5) 0.0258(6) 0.0020(4) 0.0026(4) 0.0027(3) N1' 0.0140(6) 0.0088(8) 0.0236(10) 0.0009(7) 0.0041(6) 0.0003(5) N3' 0.0140(8) 0.0088(8) 0.0232(13) 0.0005(7) 0.0042(7) 0.0007(6) C2' 0.0151(7) 0.0110(11) 0.0185(6) 0.0000(6) 0.0041(6) 0.0010(5) C4' 0.0149(8) 0.0146(6) 0.0177(10) -0.0004(7) 0.0047(6) 0.0008(5) C5' 0.0129(6) 0.0134(8) 0.0188(7) 0.0005(4) 0.0035(5) -0.0006(4) C6' 0.0147(6) 0.0134(7) 0.0171(9) -0.0003(6) 0.0038(7) -0.0022(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl9 C5 1.720(3) . ? O7 C2 1.242(3) . ? O8 C4 1.227(5) . ? N1 C2 1.356(4) . ? N1 C6 1.372(4) . ? N1 H1 0.8800 . ? N3 C2 1.371(3) . ? N3 C4 1.395(4) . ? N3 H3 0.8800 . ? C4 C5 1.460(4) . ? C5 C6 1.343(4) . ? C6 H6 0.9500 . ? Cl9' C5' 1.732(15) . ? O7' C2' 1.245(15) . ? O8' C4' 1.234(17) . ? N1' C2' 1.343(18) . ? N1' C6' 1.374(18) . ? N1' H1' 0.8800 . ? N3' C2' 1.376(19) . ? N3' C4' 1.403(18) . ? N3' H3' 0.8800 . ? C4' C5' 1.465(18) . ? C5' C6' 1.352(19) . ? C6' H6' 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C6 122.2(4) . . ? C2 N1 H1 118.9 . . ? C6 N1 H1 118.9 . . ? C2 N3 C4 126.5(4) . . ? C2 N3 H3 116.8 . . ? C4 N3 H3 116.8 . . ? O7 C2 N1 122.6(5) . . ? O7 C2 N3 121.2(5) . . ? N1 C2 N3 116.2(3) . . ? O8 C4 N3 120.8(4) . . ? O8 C4 C5 126.1(4) . . ? N3 C4 C5 113.1(4) . . ? C6 C5 C4 120.6(3) . . ? C6 C5 Cl9 120.5(3) . . ? C4 C5 Cl9 118.9(3) . . ? C5 C6 N1 121.3(3) . . ? C5 C6 H6 119.3 . . ? N1 C6 H6 119.3 . . ? C2' N1' C6' 124(2) . . ? C2' N1' H1' 118.2 . . ? C6' N1' H1' 118.2 . . ? C2' N3' C4' 125(2) . . ? C2' N3' H3' 117.3 . . ? C4' N3' H3' 117.3 . . ? O7' C2' N1' 124(3) . . ? O7' C2' N3' 119(3) . . ? N1' C2' N3' 117.2(17) . . ? O8' C4' N3' 120(2) . . ? O8' C4' C5' 127.6(19) . . ? N3' C4' C5' 112.4(17) . . ? C6' C5' C4' 122.7(15) . . ? C6' C5' Cl9' 117.2(17) . . ? C4' C5' Cl9' 120.1(16) . . ? C5' C6' N1' 119(2) . . ? C5' C6' H6' 120.6 . . ? N1' C6' H6' 120.6 . . ? 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 N1 C2 O7 -177.44(16) . . . . ? C6 N1 C2 N3 2.9(2) . . . . ? C4 N3 C2 O7 177.45(16) . . . . ? C4 N3 C2 N1 -2.9(3) . . . . ? C2 N3 C4 O8 -179.8(2) . . . . ? C2 N3 C4 C5 0.8(2) . . . . ? O8 C4 C5 C6 -178.0(3) . . . . ? N3 C4 C5 C6 1.4(2) . . . . ? O8 C4 C5 Cl9 1.6(3) . . . . ? N3 C4 C5 Cl9 -178.99(11) . . . . ? C4 C5 C6 N1 -1.4(3) . . . . ? Cl9 C5 C6 N1 179.02(12) . . . . ? C2 N1 C6 C5 -0.9(3) . . . . ? C6' N1' C2' O7' -180.0(3) . . . . ? C6' N1' C2' N3' 0.0(4) . . . . ? C4' N3' C2' O7' 180.0(3) . . . . ? C4' N3' C2' N1' 0.0(4) . . . . ? C2' N3' C4' O8' 180.0(3) . . . . ? C2' N3' C4' C5' 0.0(4) . . . . ? O8' C4' C5' C6' 180.0(3) . . . . ? N3' C4' C5' C6' 0.0(4) . . . . ? O8' C4' C5' Cl9' 0.0(4) . . . . ? N3' C4' C5' Cl9' 180.0(2) . . . . ? C4' C5' C6' N1' 0.0(4) . . . . ? Cl9' C5' C6' N1' -180.0(2) . . . . ? C2' N1' C6' C5' -0.1(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O7 0.88 1.89 2.760(11) 171.0 3_565 N3 H3 O7 0.88 1.95 2.818(11) 169.4 3 N1' H1' O7' 0.88 1.91 2.76(6) 164.0 3 N3' H3' O7' 0.88 2.03 2.91(7) 174.7 3_565 _diffrn_measured_fraction_theta_max 0.949 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.404 _refine_diff_density_min -0.696 _refine_diff_density_rms 0.082 data_STR0480 _database_code_depnum_ccdc_archive 'CCDC 693303' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 5-Bromouracil ; _chemical_name_common 'C4 H3 Br N2 O2' _chemical_melting_point ? _chemical_formula_moiety 'C4 H3 Br N2 O2' _chemical_formula_sum 'C4 H3 Br N2 O2' _chemical_formula_weight 190.99 _exptl_special_details ; The 5-bromouracil was found to exhibit complete molecule disorder about the C5-Br9 axis. The disorder was modelled anisotropically over two sites for all of the atoms with occupancy ratios of 73:27. The minor component was restrained to be flat and geometrically similar to the major component. Suitable restraints were also applied to the thermal parameters of the minor component (SIMU DELU EADP). The hydrogen atoms were geometrically placed on all atoms as necessary within the part instructions. ; 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n 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' _cell_length_a 8.5680(11) _cell_length_b 6.8823(9) _cell_length_c 9.5715(12) _cell_angle_alpha 90.00 _cell_angle_beta 103.440(2) _cell_angle_gamma 90.00 _cell_volume 548.95(12) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2447 _cell_measurement_theta_min 2.877 _cell_measurement_theta_max 28.237 _exptl_crystal_description 'Lozenge-shaped block' _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.311 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 368 _exptl_absorpt_coefficient_mu 7.397 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5375 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS v2.03' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 4554 _diffrn_reflns_av_R_equivalents 0.0212 _diffrn_reflns_av_sigmaI/netI 0.0239 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.88 _diffrn_reflns_theta_max 28.24 _reflns_number_total 1305 _reflns_number_gt 1172 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0260P)^2^+0.6517P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1305 _refine_ls_number_parameters 109 _refine_ls_number_restraints 96 _refine_ls_R_factor_all 0.0283 _refine_ls_R_factor_gt 0.0254 _refine_ls_wR_factor_ref 0.0630 _refine_ls_wR_factor_gt 0.0623 _refine_ls_goodness_of_fit_ref 1.112 _refine_ls_restrained_S_all 1.077 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br9 Br 0.68462(16) 0.27128(9) 0.20161(16) 0.01350(15) Uani 0.73 1 d PD A 1 O7 O -0.0194(9) 0.246(3) -0.0083(8) 0.0135(10) Uani 0.73 1 d PD A 1 O8 O 0.4458(3) -0.0879(3) 0.1534(2) 0.0155(4) Uani 0.73 1 d PD A 1 N1 N 0.2098(9) 0.4192(10) 0.0639(4) 0.0104(7) Uani 0.73 1 d PD A 1 H1 H 0.1568 0.5296 0.0483 0.013 Uiso 0.73 1 calc PR A 1 N3 N 0.2159(11) 0.0840(14) 0.0778(9) 0.0145(8) Uani 0.73 1 d PD A 1 H3 H 0.1624 -0.0262 0.0691 0.017 Uiso 0.73 1 calc PR A 1 C2 C 0.1271(9) 0.2502(18) 0.0409(8) 0.0114(6) Uani 0.73 1 d PD A 1 C4 C 0.3828(9) 0.0716(10) 0.1276(6) 0.0125(8) Uani 0.73 1 d PD A 1 C5 C 0.4609(6) 0.2617(9) 0.1411(5) 0.0110(5) Uani 0.73 1 d PD A 1 C6 C 0.3731(8) 0.4234(8) 0.1109(4) 0.0112(7) Uani 0.73 1 d PD A 1 H6 H 0.4261 0.5457 0.1224 0.013 Uiso 0.73 1 calc PR A 1 Br9' Br 0.6833(5) 0.2329(4) 0.2051(5) 0.01350(15) Uani 0.27 1 d PDU B 2 O7' O -0.021(2) 0.254(7) 0.011(3) 0.0135(10) Uani 0.27 1 d PDU B 2 O8' O 0.4439(7) 0.5943(8) 0.1526(7) 0.0155(4) Uani 0.27 1 d PDU B 2 N1' N 0.210(3) 0.084(4) 0.069(2) 0.0104(7) Uani 0.27 1 d PDU B 2 H1' H 0.1567 -0.0259 0.0497 0.013 Uiso 0.27 1 calc PR B 2 N3' N 0.215(2) 0.419(3) 0.0828(14) 0.0145(8) Uani 0.27 1 d PDU B 2 H3' H 0.1618 0.5294 0.0722 0.017 Uiso 0.27 1 calc PR B 2 C2' C 0.126(2) 0.253(5) 0.052(2) 0.0114(6) Uani 0.27 1 d PDU B 2 C4' C 0.384(2) 0.433(2) 0.1299(9) 0.0125(8) Uani 0.27 1 d PDU B 2 C5' C 0.4590(15) 0.240(2) 0.1434(10) 0.0110(5) Uani 0.27 1 d PDU B 2 C6' C 0.373(2) 0.077(3) 0.1134(17) 0.0112(7) Uani 0.27 1 d PDU B 2 H6' H 0.4256 -0.0456 0.1235 0.013 Uiso 0.27 1 calc PR B 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br9 0.00802(14) 0.0106(4) 0.02097(17) 0.0035(3) 0.00153(10) -0.0007(3) O7 0.0086(7) 0.0110(16) 0.021(2) -0.002(3) 0.0036(12) 0.0002(6) O8 0.0124(10) 0.0096(9) 0.0225(11) 0.0020(7) 0.0003(8) 0.0016(7) N1 0.0085(11) 0.0083(9) 0.0143(19) 0.0001(16) 0.0021(14) 0.0000(8) N3 0.0104(12) 0.0081(10) 0.025(2) 0.0013(14) 0.0035(14) 0.0001(8) C2 0.0107(9) 0.0111(9) 0.0132(15) -0.0008(12) 0.0042(10) -0.0001(6) C4 0.0098(12) 0.0131(10) 0.014(2) 0.0003(14) 0.0016(15) 0.0002(9) C5 0.0091(9) 0.0104(13) 0.0142(10) 0.0003(8) 0.0040(8) -0.0018(8) C6 0.0098(12) 0.0115(11) 0.0120(17) -0.0010(13) 0.0020(15) -0.0018(9) Br9' 0.00802(14) 0.0106(4) 0.02097(17) 0.0035(3) 0.00153(10) -0.0007(3) O7' 0.0086(7) 0.0110(16) 0.021(2) -0.002(3) 0.0036(12) 0.0002(6) O8' 0.0124(10) 0.0096(9) 0.0225(11) 0.0020(7) 0.0003(8) 0.0016(7) N1' 0.0085(11) 0.0083(9) 0.0143(19) 0.0001(16) 0.0021(14) 0.0000(8) N3' 0.0104(12) 0.0081(10) 0.025(2) 0.0013(14) 0.0035(14) 0.0001(8) C2' 0.0107(9) 0.0111(9) 0.0132(15) -0.0008(12) 0.0042(10) -0.0001(6) C4' 0.0098(12) 0.0131(10) 0.014(2) 0.0003(14) 0.0016(15) 0.0002(9) C5' 0.0091(9) 0.0104(13) 0.0142(10) 0.0003(8) 0.0040(8) -0.0018(8) C6' 0.0098(12) 0.0115(11) 0.0120(17) -0.0010(13) 0.0020(15) -0.0018(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br9 C5 1.871(5) . ? O7 C2 1.234(6) . ? O8 C4 1.223(7) . ? N1 C2 1.353(9) . ? N1 C6 1.367(7) . ? N1 H1 0.8800 . ? N3 C2 1.374(9) . ? N3 C4 1.401(8) . ? N3 H3 0.8800 . ? C4 C5 1.461(8) . ? C5 C6 1.337(7) . ? C6 H6 0.9500 . ? Br9' C5' 1.876(12) . ? O7' C2' 1.234(14) . ? O8' C4' 1.225(14) . ? N1' C2' 1.35(2) . ? N1' C6' 1.360(19) . ? N1' H1' 0.8800 . ? N3' C2' 1.37(2) . ? N3' C4' 1.409(19) . ? N3' H3' 0.8800 . ? C4' C5' 1.466(19) . ? C5' C6' 1.340(19) . ? C6' H6' 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C6 121.9(7) . . ? C2 N1 H1 119.0 . . ? C6 N1 H1 119.0 . . ? C2 N3 C4 126.8(8) . . ? C2 N3 H3 116.6 . . ? C4 N3 H3 116.6 . . ? O7 C2 N1 121.9(12) . . ? O7 C2 N3 122.3(11) . . ? N1 C2 N3 115.9(6) . . ? O8 C4 N3 119.4(7) . . ? O8 C4 C5 127.9(6) . . ? N3 C4 C5 112.7(6) . . ? C6 C5 C4 120.2(4) . . ? C6 C5 Br9 121.5(5) . . ? C4 C5 Br9 118.3(5) . . ? C5 C6 N1 122.3(5) . . ? C5 C6 H6 118.8 . . ? N1 C6 H6 118.8 . . ? C2' N1' C6' 123(2) . . ? C2' N1' H1' 118.5 . . ? C6' N1' H1' 118.5 . . ? C2' N3' C4' 126.8(19) . . ? C2' N3' H3' 116.6 . . ? C4' N3' H3' 116.6 . . ? O7' C2' N1' 121(3) . . ? O7' C2' N3' 123(3) . . ? N1' C2' N3' 116.1(16) . . ? O8' C4' N3' 118.3(16) . . ? O8' C4' C5' 130.3(16) . . ? N3' C4' C5' 111.5(14) . . ? C6' C5' C4' 122.0(12) . . ? C6' C5' Br9' 121.3(14) . . ? C4' C5' Br9' 116.7(12) . . ? C5' C6' N1' 120.7(18) . . ? C5' C6' H6' 119.7 . . ? N1' C6' H6' 119.7 . . ? 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 N1 C2 O7 -176.3(3) . . . . ? C6 N1 C2 N3 4.7(5) . . . . ? C4 N3 C2 O7 176.7(4) . . . . ? C4 N3 C2 N1 -4.3(5) . . . . ? C2 N3 C4 O8 -178.5(5) . . . . ? C2 N3 C4 C5 1.1(5) . . . . ? O8 C4 C5 C6 -178.7(5) . . . . ? N3 C4 C5 C6 1.8(5) . . . . ? O8 C4 C5 Br9 1.2(6) . . . . ? N3 C4 C5 Br9 -178.3(2) . . . . ? C4 C5 C6 N1 -1.4(5) . . . . ? Br9 C5 C6 N1 178.7(2) . . . . ? C2 N1 C6 C5 -2.1(5) . . . . ? C6' N1' C2' O7' -180.0(3) . . . . ? C6' N1' C2' N3' 0.0(4) . . . . ? C4' N3' C2' O7' 180.0(3) . . . . ? C4' N3' C2' N1' 0.0(4) . . . . ? C2' N3' C4' O8' -180.0(3) . . . . ? C2' N3' C4' C5' 0.0(4) . . . . ? O8' C4' C5' C6' 180.0(3) . . . . ? N3' C4' C5' C6' 0.0(4) . . . . ? O8' C4' C5' Br9' 0.0(4) . . . . ? N3' C4' C5' Br9' 180.0(2) . . . . ? C4' C5' C6' N1' 0.1(4) . . . . ? Br9' C5' C6' N1' -180.0(2) . . . . ? C2' N1' C6' C5' -0.1(5) . . . . ? _diffrn_measured_fraction_theta_max 0.956 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.441 _refine_diff_density_min -0.625 _refine_diff_density_rms 0.100 #===END