# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_New_Global_Publ_Block _journal_name_full CrystEngComm _journal_coden_cambridge 1350 #TrackingRef 'CIF_neu.cif' # Loop of author details loop_ _publ_author_name _publ_author_address _publ_author_footnote T.Gelbrich ; Institut f\"ur Pharmazie Universit\"at Innsbruck Innrain 52 6020 Innsbruck Austria ; . D.Rossi ; Institut f\"ur Pharmazie Universit\"at Innsbruck Innrain 52 6020 Innsbruck Austria ; . C.Hafele ; Institut f\"ur Pharmazie Universit\"at Innsbruck Innrain 52 6020 Innsbruck Austria ; . U.J.Griesser ; Institut f\"ur Pharmazie Universit\"at Innsbruck Innrain 52 6020 Innsbruck Austria ; . # Added by publCIF - use a unique identifier for each data block #============================================================================== # SUBMISSION DETAILS _publ_contact_author_name 'Thomas Gelbrich' # Name of author for correspondence _publ_contact_author_address # Address of author for correspondence ; Universitt Insbruck Institut f\"ur Pharnazie 6020 Innsbruck Austria ; _publ_contact_author_email thomas.gelbrich@uibk.ac.uk _publ_contact_author_fax ? _publ_contact_author_phone ? #============================================================================== # Formatted by publCIF data_1 _database_code_depnum_ccdc_archive 'CCDC 819517' #TrackingRef 'CIF_neu.cif' _audit_update_record ; 2011-03-30 # Formatted by publCIF ; _chemical_name_systematic ; 5-Isopropyl-5-(2-bromoallyl)-barbituric acid ; _chemical_name_common 'propallylonal, noctal, nostal, quietal, ibomal' _chemical_melting_point 449 _chemical_formula_moiety 'C10 H13 Br N2 O3' _chemical_formula_sum 'C10 H13 Br N2 O3' _chemical_formula_weight 289.13 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' O O 0.0106 0.0060 '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' 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 P21/c _symmetry_space_group_name_Hall '-P 2ybc' 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 8.0916(3) _cell_length_b 11.3472(5) _cell_length_c 13.2670(4) _cell_angle_alpha 90.00 _cell_angle_beta 105.773(2) _cell_angle_gamma 90.00 _cell_volume 1172.27(8) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3846 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 26.02 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.638 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 3.501 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8444 _exptl_absorpt_correction_T_max 0.8444 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; Polymorphic form II of noctal. Previously described in: A. Kofler, Arch. Pharm. Ber. Deut. Pharm. Ges., 1943, 281, 8-22. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius APEX II CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_reflns_number 11500 _diffrn_reflns_av_R_equivalents 0.0765 _diffrn_reflns_av_sigmaI/netI 0.0579 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.53 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2277 _reflns_number_gt 1745 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0258P)^2^+2.5250P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2277 _refine_ls_number_parameters 166 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0671 _refine_ls_R_factor_gt 0.0439 _refine_ls_wR_factor_ref 0.0992 _refine_ls_wR_factor_gt 0.0920 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.051 _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 Br1 Br 0.39554(6) 0.15893(4) -0.06963(3) 0.03188(16) Uani 1 1 d . . . N1 N 0.8143(4) 0.2637(3) -0.0839(2) 0.0163(6) Uani 1 1 d D . . H1 H 0.816(6) 0.285(4) -0.147(2) 0.037(13) Uiso 1 1 d D . . N3 N 0.8801(4) 0.1261(3) 0.0526(2) 0.0166(6) Uani 1 1 d D . . H3 H 0.933(5) 0.059(2) 0.074(3) 0.024(11) Uiso 1 1 d D . . O2 O 0.9511(4) 0.0938(2) -0.09921(18) 0.0246(6) Uani 1 1 d . . . O4 O 0.8224(3) 0.1578(2) 0.20678(17) 0.0184(5) Uani 1 1 d . . . O6 O 0.6439(3) 0.4202(2) -0.08176(18) 0.0186(5) Uani 1 1 d . . . C2 C 0.8850(4) 0.1582(3) -0.0470(2) 0.0158(7) Uani 1 1 d . . . C4 C 0.8147(4) 0.1933(3) 0.1189(3) 0.0149(7) Uani 1 1 d . . . C5 C 0.7351(4) 0.3115(3) 0.0795(3) 0.0137(7) Uani 1 1 d . . . C6 C 0.7230(4) 0.3372(3) -0.0343(3) 0.0151(7) Uani 1 1 d . . . C7 C 0.5548(5) 0.3193(3) 0.0995(3) 0.0185(8) Uani 1 1 d . . . H7A H 0.5698 0.3382 0.1742 0.025(11) Uiso 1 1 calc R . . H7B H 0.4911 0.3854 0.0576 0.019(10) Uiso 1 1 calc R . . C8 C 0.4479(5) 0.2094(3) 0.0731(3) 0.0246(8) Uani 1 1 d . . . C9 C 0.3874(6) 0.1471(4) 0.1396(4) 0.0372(11) Uani 1 1 d . . . H9A H 0.4107 0.1710 0.2107 0.036(13) Uiso 1 1 calc R . . H9B H 0.3207 0.0785 0.1161 0.031(11) Uiso 1 1 calc R . . C10 C 0.8597(5) 0.4065(3) 0.1493(3) 0.0183(8) Uani 1 1 d . . . H10 H 0.8657 0.3872 0.2238 0.019(10) Uiso 1 1 calc R . . C11 C 0.7936(5) 0.5321(3) 0.1315(3) 0.0216(8) Uani 1 1 d . . . H11A H 0.6769 0.5359 0.1396 0.034(12) Uiso 1 1 calc R . . H11B H 0.7923 0.5571 0.0606 0.022(10) Uiso 1 1 calc R . . H11C H 0.8690 0.5843 0.1828 0.024(10) Uiso 1 1 calc R . . C12 C 1.0431(4) 0.3969(3) 0.1397(3) 0.0205(8) Uani 1 1 d . . . H12A H 1.0861 0.3168 0.1579 0.025(11) Uiso 1 1 calc R . . H12B H 1.1167 0.4532 0.1875 0.013(9) Uiso 1 1 calc R . . H12C H 1.0441 0.4146 0.0676 0.043(13) Uiso 1 1 calc R . . 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 Br1 0.0334(3) 0.0280(2) 0.0324(3) -0.00605(18) 0.00576(17) -0.00798(19) N1 0.0231(16) 0.0148(15) 0.0120(15) 0.0031(12) 0.0064(12) 0.0043(13) N3 0.0218(17) 0.0155(16) 0.0131(15) 0.0012(11) 0.0058(12) 0.0053(13) O2 0.0387(16) 0.0227(15) 0.0152(13) 0.0025(11) 0.0122(11) 0.0135(13) O4 0.0279(14) 0.0170(13) 0.0109(12) 0.0051(10) 0.0062(10) 0.0082(11) O6 0.0243(13) 0.0133(13) 0.0174(12) 0.0029(10) 0.0044(10) 0.0063(11) C2 0.0196(18) 0.0168(18) 0.0111(17) 0.0030(14) 0.0042(14) 0.0045(15) C4 0.0129(16) 0.0142(17) 0.0166(18) -0.0029(13) 0.0022(13) -0.0004(14) C5 0.0172(17) 0.0091(17) 0.0153(17) 0.0020(12) 0.0053(13) 0.0052(13) C6 0.0171(17) 0.0125(17) 0.0150(17) -0.0034(14) 0.0031(13) -0.0045(15) C7 0.0217(19) 0.0167(19) 0.0183(18) 0.0014(14) 0.0077(14) 0.0011(15) C8 0.020(2) 0.019(2) 0.033(2) 0.0014(16) 0.0058(16) 0.0027(17) C9 0.035(2) 0.035(3) 0.045(3) -0.003(2) 0.017(2) -0.007(2) C10 0.0227(19) 0.0175(19) 0.0124(17) 0.0000(14) 0.0007(14) -0.0005(15) C11 0.023(2) 0.0153(19) 0.026(2) -0.0041(15) 0.0062(16) 0.0000(16) C12 0.0154(18) 0.0164(19) 0.028(2) -0.0040(15) 0.0027(15) 0.0019(15) _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 Br1 C8 1.913(4) . ? N1 C2 1.360(4) . ? N1 C6 1.392(4) . ? N1 H1 0.871(19) . ? N3 C4 1.374(4) . ? N3 C2 1.381(4) . ? N3 H3 0.875(19) . ? O2 C2 1.225(4) . ? O4 C4 1.220(4) . ? O6 C6 1.214(4) . ? C4 C5 1.517(5) . ? C5 C6 1.515(5) . ? C5 C7 1.554(5) . ? C5 C10 1.590(5) . ? C7 C8 1.504(5) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.324(6) . ? C9 H9A 0.9500 . ? C9 H9B 0.9500 . ? C10 C11 1.518(5) . ? C10 C12 1.527(5) . ? C10 H10 1.0000 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? 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 125.6(3) . . ? C2 N1 H1 119(3) . . ? C6 N1 H1 115(3) . . ? C4 N3 C2 125.6(3) . . ? C4 N3 H3 121(3) . . ? C2 N3 H3 113(3) . . ? O2 C2 N1 121.8(3) . . ? O2 C2 N3 121.0(3) . . ? N1 C2 N3 117.2(3) . . ? O4 C4 N3 120.0(3) . . ? O4 C4 C5 121.8(3) . . ? N3 C4 C5 118.2(3) . . ? C6 C5 C4 114.8(3) . . ? C6 C5 C7 110.4(3) . . ? C4 C5 C7 108.8(3) . . ? C6 C5 C10 108.0(3) . . ? C4 C5 C10 104.9(3) . . ? C7 C5 C10 109.8(3) . . ? O6 C6 N1 119.4(3) . . ? O6 C6 C5 123.3(3) . . ? N1 C6 C5 117.2(3) . . ? C8 C7 C5 114.8(3) . . ? C8 C7 H7A 108.6 . . ? C5 C7 H7A 108.6 . . ? C8 C7 H7B 108.6 . . ? C5 C7 H7B 108.6 . . ? H7A C7 H7B 107.5 . . ? C9 C8 C7 125.6(4) . . ? C9 C8 Br1 118.5(3) . . ? C7 C8 Br1 115.9(3) . . ? C8 C9 H9A 120.0 . . ? C8 C9 H9B 120.0 . . ? H9A C9 H9B 120.0 . . ? C11 C10 C12 111.3(3) . . ? C11 C10 C5 113.9(3) . . ? C12 C10 C5 112.3(3) . . ? C11 C10 H10 106.2 . . ? C12 C10 H10 106.2 . . ? C5 C10 H10 106.2 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? 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 O4 0.871(19) 2.06(2) 2.934(4) 178(4) 4_565 N3 H3 O2 0.875(19) 1.96(2) 2.832(4) 172(4) 3_755 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.436 _refine_diff_density_min -0.545 _refine_diff_density_rms 0.101 data_2a _database_code_depnum_ccdc_archive 'CCDC 819518' #TrackingRef 'CIF_neu.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 5,5-dichlorobarbituric acid ; _chemical_name_common ? _chemical_melting_point 473 _chemical_formula_moiety 'C4 H2 Cl2 N2 O3' _chemical_formula_sum 'C4 H2 Cl2 N2 O3' _chemical_formula_weight 196.98 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 Cc _symmetry_space_group_name_Hall 'C -2yc ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 11.5440(3) _cell_length_b 11.5528(3) _cell_length_c 20.0656(5) _cell_angle_alpha 90.00 _cell_angle_beta 100.481(3) _cell_angle_gamma 90.00 _cell_volume 2631.41(12) _cell_formula_units_Z 16 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5077 _cell_measurement_theta_min 3.2786 _cell_measurement_theta_max 27.8760 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.989 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1568 _exptl_absorpt_coefficient_mu 0.936 _exptl_absorpt_correction_T_min 0.89902 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; monoclinic polymorph ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Ruby, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3575 _diffrn_reflns_number 6733 _diffrn_reflns_av_R_equivalents 0.0310 _diffrn_reflns_av_sigmaI/netI 0.0320 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.46 _diffrn_reflns_theta_max 25.99 _reflns_number_total 3529 _reflns_number_gt 3225 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0352P)^2^+0.0000P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(4) _refine_ls_number_reflns 3529 _refine_ls_number_parameters 421 _refine_ls_number_restraints 10 _refine_ls_R_factor_all 0.0261 _refine_ls_R_factor_gt 0.0235 _refine_ls_wR_factor_ref 0.0572 _refine_ls_wR_factor_gt 0.0567 _refine_ls_goodness_of_fit_ref 0.983 _refine_ls_restrained_S_all 0.982 _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 Cl1A Cl 0.92908(7) 0.92091(7) 0.50019(5) 0.0202(2) Uani 1 1 d . . . Cl2A Cl 0.89941(7) 0.70959(7) 0.41977(4) 0.02113(19) Uani 1 1 d . . . N1A N 0.7474(2) 0.6779(2) 0.55574(15) 0.0156(6) Uani 1 1 d D . . H1A H 0.750(3) 0.638(3) 0.5926(12) 0.019 Uiso 1 1 d D . . N3A N 0.6306(2) 0.7665(2) 0.46243(13) 0.0132(6) Uani 1 1 d D . . H3A H 0.5591(18) 0.781(3) 0.4428(16) 0.016 Uiso 1 1 d D . . O2A O 0.55057(17) 0.64652(18) 0.53069(11) 0.0172(5) Uani 1 1 d . . . O4A O 0.7021(2) 0.90652(19) 0.40286(12) 0.0173(5) Uani 1 1 d . . . O6A O 0.94320(19) 0.7026(2) 0.58084(13) 0.0244(6) Uani 1 1 d . . . C2A C 0.6372(3) 0.6931(3) 0.51696(17) 0.0133(7) Uani 1 1 d . . . C4A C 0.7183(3) 0.8309(3) 0.44451(16) 0.0135(7) Uani 1 1 d . . . C5A C 0.8422(3) 0.7961(3) 0.47980(18) 0.0128(7) Uani 1 1 d . . . C6A C 0.8514(3) 0.7215(3) 0.54415(16) 0.0139(7) Uani 1 1 d . . . Cl1B Cl 0.39869(8) 0.52123(8) 0.80488(5) 0.0243(2) Uani 1 1 d . . . Cl2B Cl 0.36994(8) 0.31129(7) 0.72370(5) 0.0210(2) Uani 1 1 d . . . N1B N 0.5510(3) 0.5550(2) 0.66908(15) 0.0179(7) Uani 1 1 d D . . H1B H 0.549(3) 0.599(3) 0.6340(13) 0.022 Uiso 1 1 d D . . N3B N 0.6679(2) 0.4679(2) 0.76276(14) 0.0139(6) Uani 1 1 d D . . H3B H 0.7368(19) 0.458(3) 0.7855(15) 0.017 Uiso 1 1 d D . . O2B O 0.74738(18) 0.58659(19) 0.69320(12) 0.0170(5) Uani 1 1 d . . . O4B O 0.5978(2) 0.32481(19) 0.82058(13) 0.0194(6) Uani 1 1 d . . . O6B O 0.3545(2) 0.5305(2) 0.64385(13) 0.0269(6) Uani 1 1 d . . . C2B C 0.6609(3) 0.5400(3) 0.70738(17) 0.0119(7) Uani 1 1 d . . . C4B C 0.5790(3) 0.4007(3) 0.77909(16) 0.0134(7) Uani 1 1 d . . . C5B C 0.4549(3) 0.4354(3) 0.74383(17) 0.0135(7) Uani 1 1 d . . . C6B C 0.4470(3) 0.5107(3) 0.68090(17) 0.0161(7) Uani 1 1 d . . . Cl1C Cl 0.61750(7) -0.20023(7) 0.79965(4) 0.0228(2) Uani 1 1 d . . . Cl2C Cl 0.37961(7) -0.20165(7) 0.72238(5) 0.0211(2) Uani 1 1 d . . . N1C N 0.6029(2) 0.0000(2) 0.66646(14) 0.0160(6) Uani 1 1 d D . . H1C H 0.625(3) 0.013(3) 0.6291(12) 0.019 Uiso 1 1 d D . . N3C N 0.5476(2) 0.0843(2) 0.76181(13) 0.0136(6) Uani 1 1 d D . . H3C H 0.545(3) 0.147(2) 0.7836(16) 0.016 Uiso 1 1 d D . . O2C O 0.64280(19) 0.18792(18) 0.69296(12) 0.0162(5) Uani 1 1 d . . . O4C O 0.42751(18) -0.0088(2) 0.82131(12) 0.0195(5) Uani 1 1 d . . . O6C O 0.5703(2) -0.18803(19) 0.64016(13) 0.0274(6) Uani 1 1 d . . . C2C C 0.6018(3) 0.0961(3) 0.70595(17) 0.0136(7) Uani 1 1 d . . . C4C C 0.4889(3) -0.0111(3) 0.77901(17) 0.0140(7) Uani 1 1 d . . . C5C C 0.5110(3) -0.1219(3) 0.74137(16) 0.0135(7) Uani 1 1 d . . . C6C C 0.5630(3) -0.1086(3) 0.67717(16) 0.0151(7) Uani 1 1 d . . . Cl1D Cl 0.91863(8) 0.43451(7) 0.50176(5) 0.0207(2) Uani 1 1 d . . . Cl2 Cl 0.68094(8) 0.42990(7) 0.42349(5) 0.0220(2) Uani 1 1 d . . . N1D N 0.6945(3) 0.2324(2) 0.55771(15) 0.0167(6) Uani 1 1 d D . . H1D H 0.661(3) 0.227(3) 0.5927(13) 0.020 Uiso 1 1 d D . . N3D N 0.7506(2) 0.1473(2) 0.46270(13) 0.0153(6) Uani 1 1 d D . . H3D H 0.760(3) 0.082(2) 0.4413(16) 0.018 Uiso 1 1 d D . . O2D O 0.65515(19) 0.04412(18) 0.53172(12) 0.0173(5) Uani 1 1 d . . . O4D O 0.8745(2) 0.2384(2) 0.40445(12) 0.0189(6) Uani 1 1 d . . . O6D O 0.7269(2) 0.42083(18) 0.58400(13) 0.0260(6) Uani 1 1 d . . . C2D C 0.6965(3) 0.1356(3) 0.51819(16) 0.0132(7) Uani 1 1 d . . . C4D C 0.8121(3) 0.2411(3) 0.44642(16) 0.0132(7) Uani 1 1 d . . . C5D C 0.7890(3) 0.3543(3) 0.48286(17) 0.0157(7) Uani 1 1 d . . . C6D C 0.7349(3) 0.3406(3) 0.54669(16) 0.0147(7) 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 Cl1A 0.0142(4) 0.0166(4) 0.0292(5) -0.0024(4) 0.0024(4) -0.0055(3) Cl2A 0.0255(5) 0.0215(4) 0.0192(5) -0.0033(4) 0.0113(4) 0.0049(4) N1A 0.0145(15) 0.0179(16) 0.0147(15) 0.0087(11) 0.0037(13) 0.0009(11) N3A 0.0087(13) 0.0174(14) 0.0124(14) 0.0028(12) -0.0010(11) 0.0009(11) O2A 0.0160(12) 0.0184(12) 0.0182(12) 0.0001(10) 0.0056(10) -0.0059(10) O4A 0.0216(13) 0.0159(12) 0.0135(13) 0.0029(10) 0.0002(10) -0.0032(10) O6A 0.0135(13) 0.0375(15) 0.0206(14) 0.0083(11) -0.0015(12) 0.0016(10) C2A 0.0173(19) 0.0119(16) 0.0112(17) -0.0039(13) 0.0041(15) -0.0015(13) C4A 0.0180(17) 0.0117(15) 0.0112(17) -0.0042(14) 0.0039(14) 0.0024(13) C5A 0.0133(17) 0.0114(16) 0.0158(18) 0.0001(13) 0.0085(15) -0.0004(12) C6A 0.0154(17) 0.0152(17) 0.0121(17) -0.0036(13) 0.0048(14) -0.0011(13) Cl1B 0.0319(5) 0.0217(4) 0.0223(5) -0.0025(4) 0.0129(4) 0.0054(4) Cl2B 0.0164(5) 0.0171(4) 0.0294(6) -0.0034(4) 0.0041(4) -0.0047(3) N1B 0.0165(16) 0.0215(16) 0.0150(15) 0.0081(12) 0.0008(13) -0.0031(11) N3B 0.0090(12) 0.0192(14) 0.0130(14) 0.0023(12) 0.0008(11) -0.0021(11) O2B 0.0141(11) 0.0172(12) 0.0209(12) 0.0015(10) 0.0068(10) -0.0051(9) O4B 0.0200(14) 0.0177(12) 0.0196(15) 0.0065(11) 0.0009(11) -0.0020(9) O6B 0.0119(13) 0.0426(15) 0.0248(15) 0.0089(12) -0.0004(11) 0.0013(11) C2B 0.0149(17) 0.0072(15) 0.0133(17) -0.0020(13) 0.0021(15) 0.0011(12) C4B 0.0185(17) 0.0120(15) 0.0105(16) -0.0014(14) 0.0044(14) -0.0034(14) C5B 0.0130(17) 0.0161(17) 0.0120(17) -0.0039(13) 0.0036(15) -0.0030(13) C6B 0.0160(17) 0.0180(18) 0.0151(17) -0.0028(14) 0.0051(15) 0.0003(13) Cl1C 0.0217(4) 0.0276(5) 0.0173(5) 0.0065(4) -0.0012(4) 0.0087(4) Cl2C 0.0142(4) 0.0174(4) 0.0309(5) -0.0045(4) 0.0019(4) -0.0056(3) N1C 0.0239(15) 0.0136(14) 0.0135(15) -0.0008(12) 0.0109(13) -0.0031(11) N3C 0.0203(14) 0.0104(13) 0.0109(14) -0.0018(11) 0.0049(12) -0.0028(11) O2C 0.0187(12) 0.0146(12) 0.0158(12) 0.0002(10) 0.0049(10) -0.0058(9) O4C 0.0209(13) 0.0219(12) 0.0192(13) -0.0004(10) 0.0128(11) -0.0051(10) O6C 0.0488(17) 0.0157(13) 0.0209(15) -0.0051(10) 0.0152(13) -0.0020(11) C2C 0.0131(17) 0.0145(17) 0.0121(17) 0.0021(14) -0.0003(15) 0.0000(14) C4C 0.0117(16) 0.0161(16) 0.0124(17) 0.0010(13) -0.0028(14) -0.0014(13) C5C 0.0137(16) 0.0115(15) 0.0133(16) 0.0032(13) -0.0025(14) -0.0005(12) C6C 0.0165(17) 0.0141(16) 0.0144(17) 0.0043(14) 0.0021(14) -0.0006(13) Cl1D 0.0149(4) 0.0164(4) 0.0300(6) -0.0022(4) 0.0019(4) -0.0047(3) Cl2 0.0201(5) 0.0257(5) 0.0190(5) 0.0074(4) 0.0006(4) 0.0070(3) N1D 0.0236(16) 0.0137(14) 0.0149(15) -0.0006(12) 0.0094(13) -0.0033(12) N3D 0.0198(14) 0.0110(13) 0.0163(14) -0.0040(12) 0.0063(12) -0.0023(12) O2D 0.0207(12) 0.0136(12) 0.0181(12) 0.0022(9) 0.0052(10) -0.0062(9) O4D 0.0225(13) 0.0208(13) 0.0162(13) -0.0017(11) 0.0109(11) -0.0018(11) O6D 0.0469(17) 0.0147(13) 0.0189(14) -0.0029(10) 0.0124(13) -0.0022(11) C2D 0.0100(16) 0.0139(17) 0.0148(17) -0.0011(13) -0.0002(14) 0.0009(13) C4D 0.0088(15) 0.0156(16) 0.0142(17) 0.0027(13) -0.0003(14) 0.0012(12) C5D 0.0132(17) 0.0158(17) 0.0167(18) 0.0041(14) -0.0004(15) -0.0033(14) C6D 0.0203(17) 0.0100(16) 0.0122(17) 0.0006(14) -0.0009(14) 0.0021(13) _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 Cl1A C5A 1.761(3) . ? Cl2A C5A 1.782(3) . ? N1A C6A 1.361(4) . ? N1A C2A 1.376(4) . ? N3A C4A 1.356(4) . ? N3A C2A 1.375(4) . ? O2A C2A 1.211(4) . ? O4A C4A 1.200(4) . ? O6A C6A 1.195(4) . ? C4A C5A 1.531(4) . ? C5A C6A 1.540(5) . ? Cl1B C5B 1.787(3) . ? Cl2B C5B 1.742(3) . ? N1B C6B 1.365(4) . ? N1B C2B 1.370(4) . ? N3B C4B 1.374(4) . ? N3B C2B 1.379(4) . ? O2B C2B 1.212(4) . ? O4B C4B 1.202(4) . ? O6B C6B 1.207(4) . ? C4B C5B 1.531(4) . ? C5B C6B 1.522(5) . ? Cl1C C5C 1.782(3) . ? Cl2C C5C 1.756(3) . ? N1C C2C 1.365(4) . ? N1C C6C 1.367(4) . ? N3C C4C 1.370(4) . ? N3C C2C 1.386(4) . ? O2C C2C 1.209(4) . ? O4C C4C 1.201(4) . ? O6C C6C 1.193(4) . ? C4C C5C 1.532(5) . ? C5C C6C 1.525(4) . ? Cl1D C5D 1.742(3) . ? Cl2 C5D 1.788(3) . ? N1D C6D 1.367(4) . ? N1D C2D 1.373(4) . ? N3D C4D 1.367(4) . ? N3D C2D 1.379(4) . ? O2D C2D 1.211(4) . ? O4D C4D 1.204(4) . ? O6D C6D 1.206(4) . ? C4D C5D 1.545(5) . ? C5D C6D 1.532(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 C6A N1A C2A 127.6(3) . . ? C4A N3A C2A 127.8(3) . . ? O2A C2A N3A 121.8(3) . . ? O2A C2A N1A 122.1(3) . . ? N3A C2A N1A 116.1(3) . . ? O4A C4A N3A 123.7(3) . . ? O4A C4A C5A 121.8(3) . . ? N3A C4A C5A 114.4(3) . . ? C4A C5A C6A 116.8(3) . . ? C4A C5A Cl1A 109.7(2) . . ? C6A C5A Cl1A 108.3(2) . . ? C4A C5A Cl2A 105.4(2) . . ? C6A C5A Cl2A 106.0(2) . . ? Cl1A C5A Cl2A 110.55(17) . . ? O6A C6A N1A 122.6(3) . . ? O6A C6A C5A 122.5(3) . . ? N1A C6A C5A 115.0(3) . . ? C6B N1B C2B 127.5(3) . . ? C4B N3B C2B 126.6(3) . . ? O2B C2B N1B 122.0(3) . . ? O2B C2B N3B 121.8(3) . . ? N1B C2B N3B 116.2(3) . . ? O4B C4B N3B 121.9(3) . . ? O4B C4B C5B 123.1(3) . . ? N3B C4B C5B 114.8(3) . . ? C6B C5B C4B 116.2(3) . . ? C6B C5B Cl2B 109.4(2) . . ? C4B C5B Cl2B 109.4(2) . . ? C6B C5B Cl1B 106.1(2) . . ? C4B C5B Cl1B 104.7(2) . . ? Cl2B C5B Cl1B 110.88(18) . . ? O6B C6B N1B 122.0(3) . . ? O6B C6B C5B 122.1(3) . . ? N1B C6B C5B 115.9(3) . . ? C2C N1C C6C 128.0(3) . . ? C4C N3C C2C 126.8(3) . . ? O2C C2C N1C 122.9(3) . . ? O2C C2C N3C 120.8(3) . . ? N1C C2C N3C 116.3(3) . . ? O4C C4C N3C 122.9(3) . . ? O4C C4C C5C 122.6(3) . . ? N3C C4C C5C 114.4(3) . . ? C6C C5C C4C 117.3(3) . . ? C6C C5C Cl2C 109.1(2) . . ? C4C C5C Cl2C 109.3(2) . . ? C6C C5C Cl1C 105.9(2) . . ? C4C C5C Cl1C 104.9(2) . . ? Cl2C C5C Cl1C 110.00(17) . . ? O6C C6C N1C 123.0(3) . . ? O6C C6C C5C 122.1(3) . . ? N1C C6C C5C 114.9(3) . . ? C6D N1D C2D 127.5(3) . . ? C4D N3D C2D 127.0(3) . . ? O2D C2D N1D 122.2(3) . . ? O2D C2D N3D 121.4(3) . . ? N1D C2D N3D 116.4(3) . . ? O4D C4D N3D 123.3(3) . . ? O4D C4D C5D 122.0(3) . . ? N3D C4D C5D 114.6(3) . . ? C6D C5D C4D 116.1(3) . . ? C6D C5D Cl1D 109.7(2) . . ? C4D C5D Cl1D 109.8(2) . . ? C6D C5D Cl2 105.4(2) . . ? C4D C5D Cl2 104.9(2) . . ? Cl1D C5D Cl2 110.65(17) . . ? O6D C6D N1D 122.4(3) . . ? O6D C6D C5D 121.9(3) . . ? N1D C6D C5D 115.6(3) . . ? 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 N1A H1A O2B 0.866(18) 2.11(2) 2.953(4) 164(3) . N3A H3A O4D 0.865(18) 2.19(2) 2.992(4) 155(3) 3_455 N1B H1B O2A 0.866(18) 2.15(2) 2.970(4) 159(3) . N3B H3B O4C 0.849(18) 2.22(2) 3.025(3) 158(3) 3 N1C H1C O2D 0.847(18) 2.078(19) 2.920(3) 172(3) . N3C H3C O4B 0.852(18) 2.23(2) 3.033(3) 157(3) . N1D H1D O2C 0.864(18) 2.11(2) 2.928(4) 158(3) . N3D H3D O4A 0.886(18) 2.23(2) 3.041(3) 153(3) 1_545 _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.389 _refine_diff_density_min -0.230 _refine_diff_density_rms 0.056 data_2b _database_code_depnum_ccdc_archive 'CCDC 819519' #TrackingRef 'CIF_neu.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 5,5-dichlorobarbituric acid ; _chemical_name_common ? _chemical_melting_point 490 _chemical_formula_moiety 'C4 H2 Cl2 N2 O3' _chemical_formula_sum 'C4 H2 Cl2 N2 O3' _chemical_formula_weight 196.98 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 orthorhombic _symmetry_space_group_name_H-M Pbca _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 11.3096(3) _cell_length_b 12.9226(4) _cell_length_c 29.1608(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4261.8(2) _cell_formula_units_Z 24 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5454 _cell_measurement_theta_min 3.1465 _cell_measurement_theta_max 28.7370 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.842 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2352 _exptl_absorpt_coefficient_mu 0.867 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8457 _exptl_absorpt_correction_T_max 0.8457 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; orthorhombic high-temperature polymorph; isostructural with Br analogue ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Ruby, Gemini ultra' _diffrn_reflns_number 12632 _diffrn_reflns_av_R_equivalents 0.0303 _diffrn_reflns_av_sigmaI/netI 0.0332 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 3.15 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4148 _reflns_number_gt 3517 _reflns_threshold_expression >2sigma(I) _diffrn_measurement_method '\w scans' _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0236P)^2^+2.2929P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4148 _refine_ls_number_parameters 322 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0389 _refine_ls_R_factor_gt 0.0300 _refine_ls_wR_factor_ref 0.0671 _refine_ls_wR_factor_gt 0.0638 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.046 _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 Cl1A Cl 0.31978(5) 0.70600(5) 0.207453(16) 0.03829(16) Uani 1 1 d . . . Cl2A Cl 0.11537(5) 0.61744(4) 0.252945(19) 0.02942(13) Uani 1 1 d . . . N1A N 0.25598(14) 0.88126(13) 0.28685(5) 0.0176(3) Uani 1 1 d D . . H1A H 0.236(2) 0.9443(13) 0.2879(7) 0.024(6) Uiso 1 1 d D . . N3A N 0.38011(14) 0.75121(12) 0.31474(5) 0.0147(3) Uani 1 1 d D . . H3A H 0.4375(16) 0.7342(16) 0.3319(6) 0.021(6) Uiso 1 1 d D . . O2A O 0.40679(12) 0.91825(10) 0.33480(4) 0.0199(3) Uani 1 1 d . . . O4A O 0.33698(12) 0.58258(10) 0.30461(5) 0.0232(3) Uani 1 1 d . . . O6A O 0.09424(14) 0.84393(12) 0.24474(6) 0.0397(4) Uani 1 1 d . . . C2A C 0.35114(16) 0.85375(15) 0.31311(6) 0.0145(4) Uani 1 1 d . . . C4A C 0.31843(16) 0.67203(15) 0.29541(6) 0.0158(4) Uani 1 1 d . . . C5A C 0.23133(17) 0.70535(15) 0.25814(6) 0.0178(4) Uani 1 1 d . . . C6A C 0.18373(18) 0.81605(16) 0.26270(6) 0.0215(4) Uani 1 1 d . . . Cl1B Cl 0.86106(5) 0.99175(4) 0.450550(18) 0.03254(14) Uani 1 1 d . . . Cl2 Cl 0.92042(5) 0.94313(4) 0.355680(17) 0.02900(13) Uani 1 1 d . . . N1B N 0.75396(14) 0.73843(13) 0.39875(5) 0.0151(3) Uani 1 1 d D . . H1B H 0.764(2) 0.6741(13) 0.4014(7) 0.027(6) Uiso 1 1 d D . . N3B N 0.62876(15) 0.87019(13) 0.37366(6) 0.0211(4) Uani 1 1 d D . . H3B H 0.5587(16) 0.8886(18) 0.3647(7) 0.032(6) Uiso 1 1 d D . . O2B O 0.57504(12) 0.70224(10) 0.36896(4) 0.0210(3) Uani 1 1 d . . . O4B O 0.67108(13) 1.03787(11) 0.38311(5) 0.0298(3) Uani 1 1 d . . . O6B O 0.92865(12) 0.76985(11) 0.43210(5) 0.0260(3) Uani 1 1 d . . . C2B C 0.64779(16) 0.76633(15) 0.37980(6) 0.0152(4) Uani 1 1 d . . . C4B C 0.70109(17) 0.94847(15) 0.38608(6) 0.0202(4) Uani 1 1 d . . . C5B C 0.82445(16) 0.91703(15) 0.40246(6) 0.0171(4) Uani 1 1 d . . . C6B C 0.84149(16) 0.80174(15) 0.41349(6) 0.0155(4) Uani 1 1 d . . . Cl1C Cl 0.16149(5) 1.21149(5) 0.44310(2) 0.03717(15) Uani 1 1 d . . . Cl2C Cl 0.31879(5) 1.38692(4) 0.431444(17) 0.02912(13) Uani 1 1 d . . . N1C N 0.41543(14) 1.11805(13) 0.47977(5) 0.0186(4) Uani 1 1 d D . . H1C H 0.4463(19) 1.0927(16) 0.5044(6) 0.026(6) Uiso 1 1 d D . . N3C N 0.39215(15) 1.09864(13) 0.40075(5) 0.0197(4) Uani 1 1 d D . . H3C H 0.403(2) 1.0592(16) 0.3774(6) 0.030(6) Uiso 1 1 d D . . O2C O 0.47036(13) 0.97076(11) 0.44381(4) 0.0239(3) Uani 1 1 d . . . O4C O 0.35127(13) 1.23750(11) 0.35657(4) 0.0257(3) Uani 1 1 d . . . O6C O 0.37876(15) 1.26954(13) 0.51527(5) 0.0344(4) Uani 1 1 d . . . C2C C 0.42787(17) 1.05665(16) 0.44176(6) 0.0185(4) Uani 1 1 d . . . C4C C 0.35595(16) 1.19816(16) 0.39377(6) 0.0181(4) Uani 1 1 d . . . C5C C 0.31214(17) 1.25280(16) 0.43731(6) 0.0204(4) Uani 1 1 d . . . C6C C 0.37363(18) 1.21718(17) 0.48142(6) 0.0218(4) 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 Cl1A 0.0396(3) 0.0585(4) 0.0167(2) 0.0011(2) 0.0016(2) 0.0071(3) Cl2A 0.0256(3) 0.0176(3) 0.0450(3) -0.0027(2) -0.0158(2) -0.0042(2) N1A 0.0203(9) 0.0082(9) 0.0243(8) 0.0018(7) -0.0061(7) 0.0015(7) N3A 0.0150(8) 0.0113(9) 0.0178(7) 0.0010(6) -0.0053(6) 0.0015(7) O2A 0.0212(7) 0.0135(7) 0.0249(7) -0.0026(6) -0.0062(6) -0.0001(6) O4A 0.0269(8) 0.0099(7) 0.0329(7) 0.0016(6) -0.0097(6) -0.0006(6) O6A 0.0352(9) 0.0222(9) 0.0618(10) 0.0007(8) -0.0314(8) 0.0044(7) C2A 0.0156(9) 0.0126(10) 0.0154(8) 0.0010(7) 0.0004(7) -0.0004(8) C4A 0.0158(9) 0.0147(11) 0.0168(9) -0.0003(7) 0.0005(7) -0.0006(8) C5A 0.0198(10) 0.0164(10) 0.0171(9) -0.0001(7) -0.0037(7) -0.0021(8) C6A 0.0250(11) 0.0154(10) 0.0240(10) 0.0049(8) -0.0056(8) -0.0020(9) Cl1B 0.0404(3) 0.0240(3) 0.0332(3) -0.0135(2) -0.0095(2) -0.0005(2) Cl2 0.0272(3) 0.0252(3) 0.0347(3) 0.0080(2) 0.0103(2) -0.0009(2) N1B 0.0181(8) 0.0074(9) 0.0197(7) 0.0003(6) -0.0037(6) 0.0009(7) N3B 0.0157(9) 0.0107(9) 0.0368(9) -0.0011(7) -0.0083(7) 0.0017(7) O2B 0.0213(7) 0.0106(7) 0.0310(7) -0.0012(6) -0.0087(6) -0.0013(6) O4B 0.0241(8) 0.0083(8) 0.0570(9) 0.0004(7) -0.0052(7) 0.0012(6) O6B 0.0190(7) 0.0223(8) 0.0366(8) 0.0045(6) -0.0085(6) 0.0005(6) C2B 0.0173(9) 0.0111(10) 0.0171(9) -0.0013(7) 0.0003(7) 0.0012(8) C4B 0.0195(10) 0.0133(10) 0.0277(10) -0.0006(8) 0.0013(8) 0.0007(8) C5B 0.0175(9) 0.0133(10) 0.0205(9) -0.0036(8) 0.0003(7) -0.0031(8) C6B 0.0155(9) 0.0152(10) 0.0159(8) -0.0010(7) 0.0023(7) -0.0003(8) Cl1C 0.0161(3) 0.0468(4) 0.0486(3) 0.0092(3) 0.0045(2) 0.0015(2) Cl2C 0.0313(3) 0.0220(3) 0.0341(3) 0.0006(2) 0.0017(2) 0.0100(2) N1C 0.0229(9) 0.0211(9) 0.0119(7) 0.0027(7) -0.0003(6) 0.0026(7) N3C 0.0267(9) 0.0187(9) 0.0136(8) -0.0018(7) -0.0041(7) 0.0018(7) O2C 0.0335(8) 0.0182(8) 0.0202(7) 0.0010(6) -0.0051(6) 0.0029(7) O4C 0.0314(8) 0.0268(9) 0.0188(7) 0.0035(6) -0.0056(6) 0.0027(7) O6C 0.0481(10) 0.0361(10) 0.0189(7) -0.0073(7) 0.0015(7) 0.0149(8) C2C 0.0177(10) 0.0201(11) 0.0178(9) 0.0014(8) -0.0005(7) -0.0042(8) C4C 0.0140(9) 0.0218(11) 0.0187(9) 0.0001(8) -0.0038(7) -0.0004(8) C5C 0.0162(10) 0.0206(11) 0.0244(9) 0.0016(8) 0.0016(8) 0.0031(8) C6C 0.0209(10) 0.0268(12) 0.0177(9) 0.0014(9) 0.0064(8) 0.0052(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 Cl1A C5A 1.7849(19) . ? Cl2A C5A 1.742(2) . ? N1A C2A 1.368(2) . ? N1A C6A 1.369(2) . ? N1A H1A 0.846(16) . ? N3A C4A 1.361(2) . ? N3A C2A 1.366(2) . ? N3A H3A 0.849(15) . ? O2A C2A 1.221(2) . ? O4A C4A 1.205(2) . ? O6A C6A 1.195(2) . ? C4A C5A 1.529(2) . ? C5A C6A 1.534(3) . ? Cl1B C5B 1.7521(18) . ? Cl2 C5B 1.7757(19) . ? N1B C6B 1.354(2) . ? N1B C2B 1.370(2) . ? N1B H1B 0.843(16) . ? N3B C4B 1.350(3) . ? N3B C2B 1.371(2) . ? N3B H3B 0.867(16) . ? O2B C2B 1.209(2) . ? O4B C4B 1.207(2) . ? O6B C6B 1.198(2) . ? C4B C5B 1.530(3) . ? C5B C6B 1.536(3) . ? Cl1C C5C 1.793(2) . ? Cl2C C5C 1.743(2) . ? N1C C6C 1.366(3) . ? N1C C2C 1.370(2) . ? N1C H1C 0.862(15) . ? N3C C4C 1.365(3) . ? N3C C2C 1.374(2) . ? N3C H3C 0.859(16) . ? O2C C2C 1.211(2) . ? O4C C4C 1.199(2) . ? O6C C6C 1.198(2) . ? C4C C5C 1.535(3) . ? C5C C6C 1.533(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 C2A N1A C6A 126.70(17) . . ? C2A N1A H1A 116.1(15) . . ? C6A N1A H1A 116.9(15) . . ? C4A N3A C2A 126.30(16) . . ? C4A N3A H3A 116.2(15) . . ? C2A N3A H3A 117.1(15) . . ? O2A C2A N3A 121.35(17) . . ? O2A C2A N1A 121.22(17) . . ? N3A C2A N1A 117.42(16) . . ? O4A C4A N3A 122.67(17) . . ? O4A C4A C5A 122.72(17) . . ? N3A C4A C5A 114.41(16) . . ? C4A C5A C6A 115.29(15) . . ? C4A C5A Cl2A 111.32(13) . . ? C6A C5A Cl2A 110.58(14) . . ? C4A C5A Cl1A 103.23(13) . . ? C6A C5A Cl1A 105.30(13) . . ? Cl2A C5A Cl1A 110.67(10) . . ? O6A C6A N1A 123.05(19) . . ? O6A C6A C5A 122.71(18) . . ? N1A C6A C5A 114.15(16) . . ? C6B N1B C2B 127.57(17) . . ? C6B N1B H1B 117.7(16) . . ? C2B N1B H1B 114.7(16) . . ? C4B N3B C2B 127.10(17) . . ? C4B N3B H3B 115.4(16) . . ? C2B N3B H3B 116.8(16) . . ? O2B C2B N1B 121.43(17) . . ? O2B C2B N3B 121.97(17) . . ? N1B C2B N3B 116.60(16) . . ? O4B C4B N3B 121.82(18) . . ? O4B C4B C5B 122.21(18) . . ? N3B C4B C5B 115.93(17) . . ? C4B C5B C6B 115.94(16) . . ? C4B C5B Cl1B 108.60(13) . . ? C6B C5B Cl1B 109.71(13) . . ? C4B C5B Cl2 105.49(12) . . ? C6B C5B Cl2 105.57(12) . . ? Cl1B C5B Cl2 111.45(10) . . ? O6B C6B N1B 122.50(18) . . ? O6B C6B C5B 122.11(17) . . ? N1B C6B C5B 115.32(16) . . ? C6C N1C C2C 127.35(16) . . ? C6C N1C H1C 117.8(15) . . ? C2C N1C H1C 114.3(15) . . ? C4C N3C C2C 126.16(16) . . ? C4C N3C H3C 119.0(15) . . ? C2C N3C H3C 114.3(15) . . ? O2C C2C N1C 122.11(17) . . ? O2C C2C N3C 121.44(17) . . ? N1C C2C N3C 116.44(18) . . ? O4C C4C N3C 123.21(18) . . ? O4C C4C C5C 122.61(18) . . ? N3C C4C C5C 114.01(16) . . ? C6C C5C C4C 114.17(16) . . ? C6C C5C Cl2C 111.18(14) . . ? C4C C5C Cl2C 111.24(13) . . ? C6C C5C Cl1C 105.23(13) . . ? C4C C5C Cl1C 104.33(13) . . ? Cl2C C5C Cl1C 110.25(11) . . ? O6C C6C N1C 122.80(18) . . ? O6C C6C C5C 122.93(19) . . ? N1C C6C C5C 114.15(16) . . ? 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 N1A H1A O4A 0.846(16) 2.028(17) 2.853(2) 165(2) 8_665 N1B H1B O4B 0.843(16) 1.980(18) 2.765(2) 155(2) 8_755 N3A H3A O2B 0.849(15) 1.938(16) 2.786(2) 176(2) . N3B H3B O2A 0.867(16) 1.964(17) 2.823(2) 170(2) . N1C H1C O2C 0.862(15) 1.961(16) 2.820(2) 174(2) 5_676 N3C H3C O2A 0.859(16) 2.205(18) 3.026(2) 160(2) . _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.340 _refine_diff_density_min -0.385 _refine_diff_density_rms 0.058 data_3a _database_code_depnum_ccdc_archive 'CCDC 819520' #TrackingRef 'CIF_neu.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 5,5-dibromorobarbituric acid ; _chemical_name_common ? _chemical_melting_point 513 _chemical_formula_moiety 'C4 H2 Br2 N2 O3' _chemical_formula_sum 'C4 H2 Br2 N2 O3' _chemical_formula_weight 285.90 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 orthorhombic _symmetry_space_group_name_H-M Pbca _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 11.4204(2) _cell_length_b 12.9897(3) _cell_length_c 30.0304(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4454.94(18) _cell_formula_units_Z 24 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 32764 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 26.02 _exptl_crystal_description platelet _exptl_crystal_colour colourless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.558 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3216 _exptl_absorpt_coefficient_mu 10.874 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4094 _exptl_absorpt_correction_T_max 0.6124 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; orthorhombic polymorph; isostructural with Cl analogue ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius APEX II CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_reflns_number 21160 _diffrn_reflns_av_R_equivalents 0.0667 _diffrn_reflns_av_sigmaI/netI 0.0539 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 25.05 _reflns_number_total 3895 _reflns_number_gt 3103 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0152P)^2^+93.5968P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3898 _refine_ls_number_parameters 298 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0742 _refine_ls_R_factor_gt 0.0519 _refine_ls_wR_factor_ref 0.1078 _refine_ls_wR_factor_gt 0.0991 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.005 _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 Br1A Br 0.31327(8) 0.71079(9) 0.20817(3) 0.0336(3) Uani 1 1 d . . . Br2A Br 0.09997(7) 0.60903(7) 0.25906(3) 0.0229(2) Uani 1 1 d . . . N1A N 0.2527(6) 0.8796(5) 0.2925(2) 0.0213(16) Uani 1 1 d . . . H1A H 0.2362 0.9457 0.2913 0.026 Uiso 1 1 calc R . . N3A N 0.3786(6) 0.7499(5) 0.3167(2) 0.0145(15) Uani 1 1 d . . . H3A H 0.4440 0.7326 0.3303 0.017 Uiso 1 1 calc R . . O2A O 0.4065(5) 0.9162(4) 0.3376(2) 0.0214(14) Uani 1 1 d . . . O4A O 0.3367(5) 0.5824(4) 0.3058(2) 0.0202(13) Uani 1 1 d . . . O6A O 0.0870(5) 0.8445(5) 0.2544(2) 0.0291(15) Uani 1 1 d . . . C2A C 0.3495(7) 0.8530(6) 0.3166(3) 0.0159(18) Uani 1 1 d . . . C4A C 0.3148(7) 0.6712(6) 0.2975(3) 0.0149(18) Uani 1 1 d . . . C5A C 0.2252(7) 0.7066(6) 0.2635(3) 0.0159(18) Uani 1 1 d . . . C6A C 0.1778(7) 0.8148(6) 0.2696(3) 0.0183(19) Uani 1 1 d . . . Br1B Br 0.85781(8) 1.00012(7) 0.45355(3) 0.0220(2) Uani 1 1 d . . . Br2 Br 0.92832(7) 0.94504(7) 0.35250(3) 0.0206(2) Uani 1 1 d . . . N1B N 0.7535(6) 0.7399(5) 0.3982(2) 0.0151(15) Uani 1 1 d . . . H1B H 0.7668 0.6736 0.4014 0.018 Uiso 1 1 calc R . . N3B N 0.6297(6) 0.8699(5) 0.3738(2) 0.0186(16) Uani 1 1 d . . . H3B H 0.5628 0.8871 0.3613 0.022 Uiso 1 1 calc R . . O2B O 0.5748(5) 0.7025(4) 0.36979(19) 0.0178(13) Uani 1 1 d . . . O4B O 0.6713(5) 1.0378(4) 0.3812(2) 0.0223(14) Uani 1 1 d . . . O6B O 0.9259(5) 0.7709(4) 0.43214(19) 0.0186(13) Uani 1 1 d . . . C2B C 0.6485(7) 0.7661(6) 0.3796(3) 0.0164(18) Uani 1 1 d . . . C4B C 0.7016(7) 0.9492(6) 0.3851(3) 0.0166(18) Uani 1 1 d . . . C5B C 0.8219(7) 0.9177(6) 0.4022(3) 0.0135(17) Uani 1 1 d . . . C6B C 0.8400(7) 0.8037(6) 0.4126(3) 0.0149(18) Uani 1 1 d U . . Br1C Br 0.15032(7) 1.20223(7) 0.44363(3) 0.0261(2) Uani 1 1 d . . . Br2C Br 0.31820(7) 1.39601(6) 0.43273(3) 0.0211(2) Uani 1 1 d . . . N1C N 0.4190(6) 1.1161(5) 0.4798(2) 0.0152(15) Uani 1 1 d . . . H1C H 0.4399 1.0883 0.5053 0.018 Uiso 1 1 calc R . . N3C N 0.3987(6) 1.0977(5) 0.4021(2) 0.0162(15) Uani 1 1 d . . . H3C H 0.4020 1.0576 0.3785 0.019 Uiso 1 1 calc R . . O2C O 0.4806(5) 0.9719(4) 0.44384(19) 0.0210(14) Uani 1 1 d . . . O4C O 0.3488(5) 1.2346(5) 0.3595(2) 0.0226(14) Uani 1 1 d . . . O6C O 0.3746(6) 1.2648(5) 0.5151(2) 0.0304(16) Uani 1 1 d . . . C2C C 0.4354(7) 1.0571(6) 0.4418(3) 0.0134(17) Uani 1 1 d . . . C4C C 0.3569(7) 1.1966(7) 0.3960(3) 0.0198(19) Uani 1 1 d . . . C5C C 0.3138(7) 1.2485(7) 0.4386(3) 0.0190(19) Uani 1 1 d . . . C6C C 0.3728(8) 1.2148(6) 0.4815(3) 0.020(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 Br1A 0.0247(5) 0.0613(7) 0.0148(4) 0.0075(5) 0.0010(4) 0.0065(5) Br2A 0.0187(4) 0.0164(4) 0.0337(5) -0.0030(4) -0.0080(4) -0.0014(4) N1A 0.022(4) 0.007(3) 0.035(4) 0.002(3) -0.006(3) -0.001(3) N3A 0.015(3) 0.017(4) 0.012(3) 0.003(3) -0.002(3) 0.001(3) O2A 0.020(3) 0.016(3) 0.028(3) -0.008(3) -0.001(3) 0.002(3) O4A 0.022(3) 0.013(3) 0.025(3) 0.005(3) -0.009(3) 0.004(3) O6A 0.020(3) 0.025(3) 0.042(4) 0.000(3) -0.014(3) 0.002(3) C2A 0.017(4) 0.017(4) 0.013(4) -0.007(4) 0.000(3) -0.001(4) C4A 0.021(4) 0.011(4) 0.013(4) 0.002(3) -0.005(4) -0.005(3) C5A 0.011(4) 0.018(4) 0.019(4) -0.001(4) -0.001(3) -0.003(3) C6A 0.016(4) 0.017(4) 0.022(5) -0.003(4) 0.004(4) -0.002(4) Br1B 0.0277(5) 0.0177(4) 0.0206(4) -0.0063(4) -0.0033(4) -0.0010(4) Br2 0.0203(4) 0.0196(4) 0.0219(5) 0.0032(4) 0.0043(4) 0.0003(4) N1B 0.016(3) 0.010(3) 0.019(4) 0.000(3) -0.004(3) 0.002(3) N3B 0.012(3) 0.011(4) 0.033(4) -0.001(3) -0.008(3) -0.004(3) O2B 0.017(3) 0.010(3) 0.026(3) 0.000(3) -0.006(3) -0.002(2) O4B 0.016(3) 0.010(3) 0.041(4) 0.002(3) -0.004(3) 0.001(2) O6B 0.014(3) 0.017(3) 0.025(3) 0.002(3) -0.002(3) 0.002(2) C2B 0.016(4) 0.017(4) 0.016(4) -0.001(4) 0.004(4) 0.002(4) C4B 0.012(4) 0.015(4) 0.023(5) 0.001(4) -0.001(4) 0.002(4) C5B 0.014(4) 0.015(4) 0.011(4) -0.004(3) -0.006(3) 0.004(3) C6B 0.008(3) 0.018(3) 0.018(3) 0.001(3) 0.008(3) 0.000(3) Br1C 0.0145(4) 0.0317(5) 0.0323(5) 0.0070(4) 0.0019(4) 0.0000(4) Br2C 0.0220(4) 0.0174(4) 0.0238(5) 0.0000(4) 0.0017(4) 0.0050(4) N1C 0.017(4) 0.015(3) 0.014(3) 0.005(3) 0.001(3) 0.003(3) N3C 0.024(4) 0.013(4) 0.012(3) 0.000(3) -0.002(3) 0.003(3) O2C 0.023(3) 0.021(3) 0.019(3) -0.001(3) -0.003(3) 0.007(3) O4C 0.024(3) 0.020(3) 0.024(4) 0.002(3) 0.001(3) -0.001(3) O6C 0.043(4) 0.032(4) 0.016(3) -0.008(3) 0.003(3) 0.010(3) C2C 0.014(4) 0.019(4) 0.008(4) -0.001(4) -0.001(3) -0.003(4) C4C 0.014(4) 0.029(5) 0.016(5) 0.001(4) -0.003(4) -0.004(4) C5C 0.021(4) 0.019(4) 0.017(4) -0.001(4) 0.002(4) 0.003(4) C6C 0.025(5) 0.009(4) 0.025(5) 0.008(4) 0.010(4) 0.006(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 Br1A C5A 1.945(8) . ? Br2A C5A 1.916(8) . ? N1A C2A 1.366(11) . ? N1A C6A 1.382(11) . ? N1A H1A 0.8800 . ? N3A C2A 1.380(10) . ? N3A C4A 1.381(10) . ? N3A H3A 0.8800 . ? O2A C2A 1.223(10) . ? O4A C4A 1.206(9) . ? O6A C6A 1.198(10) . ? C4A C5A 1.517(11) . ? C5A C6A 1.516(11) . ? Br1B C5B 1.920(8) . ? Br2 C5B 1.958(8) . ? N1B C6B 1.359(10) . ? N1B C2B 1.367(10) . ? N1B H1B 0.8800 . ? N3B C4B 1.360(10) . ? N3B C2B 1.376(10) . ? N3B H3B 0.8800 . ? O2B C2B 1.215(10) . ? O4B C4B 1.208(10) . ? O6B C6B 1.220(9) . ? C4B C5B 1.523(11) . ? C5B C6B 1.528(11) . ? Br1C C5C 1.967(9) . ? Br2C C5C 1.926(9) . ? N1C C6C 1.386(10) . ? N1C C2C 1.387(10) . ? N1C H1C 0.8800 . ? N3C C2C 1.371(10) . ? N3C C4C 1.382(11) . ? N3C H3C 0.8800 . ? O2C C2C 1.222(10) . ? O4C C4C 1.205(10) . ? O6C C6C 1.202(10) . ? C4C C5C 1.529(12) . ? C5C C6C 1.517(12) . ? 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 C2A N1A C6A 127.6(7) . . ? C2A N1A H1A 116.2 . . ? C6A N1A H1A 116.2 . . ? C2A N3A C4A 126.2(7) . . ? C2A N3A H3A 116.9 . . ? C4A N3A H3A 116.9 . . ? O2A C2A N1A 122.3(8) . . ? O2A C2A N3A 121.5(7) . . ? N1A C2A N3A 116.2(7) . . ? O4A C4A N3A 120.9(7) . . ? O4A C4A C5A 124.6(7) . . ? N3A C4A C5A 114.3(7) . . ? C6A C5A C4A 116.1(7) . . ? C6A C5A Br2A 110.8(5) . . ? C4A C5A Br2A 110.5(5) . . ? C6A C5A Br1A 105.2(5) . . ? C4A C5A Br1A 103.6(5) . . ? Br2A C5A Br1A 110.2(4) . . ? O6A C6A N1A 121.9(8) . . ? O6A C6A C5A 124.2(8) . . ? N1A C6A C5A 113.8(7) . . ? C6B N1B C2B 128.1(7) . . ? C6B N1B H1B 116.0 . . ? C2B N1B H1B 116.0 . . ? C4B N3B C2B 128.0(7) . . ? C4B N3B H3B 116.0 . . ? C2B N3B H3B 116.0 . . ? O2B C2B N1B 122.5(8) . . ? O2B C2B N3B 121.8(7) . . ? N1B C2B N3B 115.6(7) . . ? O4B C4B N3B 121.6(7) . . ? O4B C4B C5B 123.1(7) . . ? N3B C4B C5B 115.2(7) . . ? C4B C5B C6B 116.8(7) . . ? C4B C5B Br1B 108.3(5) . . ? C6B C5B Br1B 110.4(5) . . ? C4B C5B Br2 104.7(5) . . ? C6B C5B Br2 104.3(5) . . ? Br1B C5B Br2 112.2(4) . . ? O6B C6B N1B 121.6(7) . . ? O6B C6B C5B 123.1(7) . . ? N1B C6B C5B 115.3(7) . . ? C6C N1C C2C 126.4(7) . . ? C6C N1C H1C 116.8 . . ? C2C N1C H1C 116.8 . . ? C2C N3C C4C 125.4(7) . . ? C2C N3C H3C 117.3 . . ? C4C N3C H3C 117.3 . . ? O2C C2C N3C 121.4(7) . . ? O2C C2C N1C 121.2(7) . . ? N3C C2C N1C 117.4(7) . . ? O4C C4C N3C 121.9(8) . . ? O4C C4C C5C 123.8(8) . . ? N3C C4C C5C 114.1(7) . . ? C6C C5C C4C 116.1(7) . . ? C6C C5C Br2C 110.7(6) . . ? C4C C5C Br2C 110.7(6) . . ? C6C C5C Br1C 105.6(6) . . ? C4C C5C Br1C 103.6(5) . . ? Br2C C5C Br1C 109.6(4) . . ? O6C C6C N1C 121.6(8) . . ? O6C C6C C5C 124.4(8) . . ? N1C C6C C5C 113.9(7) . . ? 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 N1A H1A O4A 0.88 2.01 2.853(9) 160.5 8_665 N1B H1B O4B 0.88 1.99 2.810(9) 153.5 8_755 N3A H3A O2B 0.88 1.95 2.818(9) 170.0 . N3B H3B O2A 0.88 1.96 2.835(9) 174.3 . N1C H1C O2C 0.88 1.94 2.808(9) 167.7 5_676 N3C H3C O2A 0.88 2.21 3.053(9) 160.2 . _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.808 _refine_diff_density_min -0.778 _refine_diff_density_rms 0.202 data_3b _database_code_depnum_ccdc_archive 'CCDC 819521' #TrackingRef 'CIF_neu.cif' _chemical_name_systematic ; 5,5-dibromorobarbituric acid ; _chemical_name_common ? _chemical_melting_point 498 _chemical_formula_moiety 'C4 H2 Br2 N2 O3' _chemical_formula_sum 'C4 H2 Br2 N2 O3' _chemical_formula_weight 285.90 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 P21/c _symmetry_space_group_name_Hall '-P 2ybc' 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 17.5105(12) _cell_length_b 6.6869(3) _cell_length_c 13.6714(9) _cell_angle_alpha 90.00 _cell_angle_beta 110.493(8) _cell_angle_gamma 90.00 _cell_volume 1499.49(16) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3336 _cell_measurement_theta_min 2.4785 _cell_measurement_theta_max 28.5960 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.533 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1072 _exptl_absorpt_coefficient_mu 10.768 _exptl_absorpt_correction_T_min 0.2220 _exptl_absorpt_correction_T_max 0.2950 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; monoclinic polymorph ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Ruby, Gemini ultra' _diffrn_detector_area_resol_mean 10.3575 _diffrn_reflns_number 8767 _diffrn_reflns_av_R_equivalents 0.0556 _diffrn_reflns_av_sigmaI/netI 0.0746 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.48 _diffrn_reflns_theta_max 25.25 _reflns_number_total 2685 _reflns_number_gt 1840 _reflns_threshold_expression >2sigma(I) _diffrn_measurement_method '\w scans' _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0314P)^2^+0.0000P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2685 _refine_ls_number_parameters 211 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0597 _refine_ls_R_factor_gt 0.0349 _refine_ls_wR_factor_ref 0.0696 _refine_ls_wR_factor_gt 0.0668 _refine_ls_goodness_of_fit_ref 0.883 _refine_ls_restrained_S_all 0.882 _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 Br1A Br 0.41455(4) 0.41658(9) 0.87560(5) 0.02490(17) Uani 1 1 d . . . Br2A Br 0.32907(4) 0.11749(8) 0.68687(5) 0.02916(19) Uani 1 1 d . . . O2A O 0.4036(3) 0.5925(6) 0.4601(3) 0.0248(10) Uani 1 1 d . . . O4A O 0.2757(3) 0.6000(6) 0.6937(3) 0.0252(10) Uani 1 1 d . . . O6A O 0.5246(2) 0.2634(6) 0.7619(3) 0.0195(9) Uani 1 1 d . . . N1A N 0.4600(3) 0.4087(7) 0.6066(4) 0.0176(11) Uani 1 1 d D . . H1A H 0.503(2) 0.390(8) 0.588(4) 0.021 Uiso 1 1 d D . . N3A N 0.3344(3) 0.5693(7) 0.5708(4) 0.0166(11) Uani 1 1 d D . . H3A H 0.298(3) 0.650(7) 0.529(3) 0.020 Uiso 1 1 d D . . C2A C 0.3997(4) 0.5291(8) 0.5407(4) 0.0172(14) Uani 1 1 d . . . C4A C 0.3280(4) 0.5290(8) 0.6651(4) 0.0166(13) Uani 1 1 d . . . C5A C 0.3880(4) 0.3719(8) 0.7299(5) 0.0171(14) Uani 1 1 d . . . C6A C 0.4660(4) 0.3440(8) 0.7041(5) 0.0164(13) Uani 1 1 d . . . Br1B Br 0.09229(4) 0.43722(9) 0.45680(5) 0.02751(18) Uani 1 1 d . . . Br2B Br 0.18678(4) 0.17514(9) 0.34270(5) 0.03037(18) Uani 1 1 d . . . O2B O 0.0948(3) 0.6025(6) 0.0413(3) 0.0274(10) Uani 1 1 d . . . O4B O 0.2106(2) 0.6864(6) 0.3876(3) 0.0226(9) Uani 1 1 d . . . O6B O -0.0169(2) 0.2783(6) 0.2472(3) 0.0235(10) Uani 1 1 d . . . N1B N 0.1599(3) 0.6188(6) 0.2163(4) 0.0162(11) Uani 1 1 d D . . H1B H 0.197(3) 0.706(6) 0.211(4) 0.019 Uiso 1 1 d D . . N3B N 0.0428(3) 0.4196(7) 0.1436(4) 0.0189(11) Uani 1 1 d D . . H3B H 0.001(2) 0.403(9) 0.085(3) 0.023 Uiso 1 1 d D . . C2B C 0.0990(3) 0.5506(8) 0.1290(5) 0.0172(14) Uani 1 1 d . . . C4B C 0.1661(4) 0.5880(8) 0.3170(5) 0.0166(13) Uani 1 1 d . . . C5B C 0.1169(3) 0.4101(8) 0.3321(4) 0.0143(12) Uani 1 1 d . . . C6B C 0.0403(4) 0.3668(8) 0.2393(4) 0.0183(14) 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 Br1A 0.0304(4) 0.0281(3) 0.0184(3) 0.0025(3) 0.0114(3) 0.0020(3) Br2A 0.0270(4) 0.0172(3) 0.0466(4) -0.0054(3) 0.0172(4) -0.0067(3) O2A 0.028(3) 0.031(2) 0.018(2) 0.008(2) 0.011(2) 0.009(2) O4A 0.026(3) 0.024(2) 0.032(3) -0.002(2) 0.017(2) 0.0129(19) O6A 0.017(3) 0.016(2) 0.023(2) 0.0052(19) 0.005(2) 0.0042(18) N1A 0.020(3) 0.019(3) 0.019(3) 0.001(2) 0.013(3) 0.008(2) N3A 0.011(3) 0.020(3) 0.018(3) 0.004(2) 0.004(2) 0.006(2) C2A 0.020(4) 0.016(3) 0.014(3) -0.005(3) 0.004(3) 0.000(3) C4A 0.014(4) 0.016(3) 0.017(3) 0.001(3) 0.002(3) -0.001(3) C5A 0.024(4) 0.008(3) 0.028(4) 0.001(2) 0.021(3) 0.000(2) C6A 0.028(4) 0.007(3) 0.016(3) 0.001(3) 0.009(3) -0.004(3) Br1B 0.0399(4) 0.0256(4) 0.0205(4) -0.0004(3) 0.0149(3) -0.0032(3) Br2B 0.0320(4) 0.0170(3) 0.0409(4) 0.0050(3) 0.0113(3) 0.0106(3) O2B 0.028(3) 0.033(3) 0.023(3) 0.005(2) 0.010(2) -0.009(2) O4B 0.016(2) 0.024(2) 0.022(2) 0.000(2) -0.001(2) -0.0047(19) O6B 0.020(3) 0.020(2) 0.030(3) 0.0009(19) 0.007(2) -0.0075(19) N1B 0.015(3) 0.011(2) 0.021(3) 0.000(2) 0.005(3) -0.004(2) N3B 0.030(3) 0.011(2) 0.019(3) -0.002(2) 0.012(3) -0.005(2) C2B 0.014(4) 0.015(3) 0.024(4) -0.001(3) 0.009(3) 0.002(3) C4B 0.016(4) 0.013(3) 0.018(3) 0.005(3) 0.003(3) 0.006(3) C5B 0.009(3) 0.014(3) 0.017(3) 0.001(2) 0.001(3) -0.001(2) C6B 0.025(4) 0.011(3) 0.025(4) 0.003(2) 0.017(3) 0.003(3) _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 Br1A C5A 1.904(6) . ? Br2A C5A 1.969(5) . ? O2A C2A 1.204(6) . ? O4A C4A 1.211(6) . ? O6A C6A 1.183(7) . ? N1A C6A 1.370(7) . ? N1A C2A 1.382(7) . ? N3A C4A 1.360(7) . ? N3A C2A 1.371(7) . ? C4A C5A 1.530(8) . ? C5A C6A 1.537(8) . ? Br1B C5B 1.907(5) . ? Br2B C5B 1.966(5) . ? O2B C2B 1.225(6) . ? O4B C4B 1.202(7) . ? O6B C6B 1.202(6) . ? N1B C4B 1.358(7) . ? N1B C2B 1.370(7) . ? N3B C6B 1.369(7) . ? N3B C2B 1.384(7) . ? C4B C5B 1.525(7) . ? C5B C6B 1.517(8) . ? 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 C6A N1A C2A 126.8(5) . . ? C4A N3A C2A 126.9(5) . . ? O2A C2A N3A 121.7(5) . . ? O2A C2A N1A 121.9(5) . . ? N3A C2A N1A 116.4(5) . . ? O4A C4A N3A 123.4(5) . . ? O4A C4A C5A 121.8(5) . . ? N3A C4A C5A 114.6(5) . . ? C4A C5A C6A 115.8(4) . . ? C4A C5A Br1A 111.4(3) . . ? C6A C5A Br1A 110.3(4) . . ? C4A C5A Br2A 103.8(4) . . ? C6A C5A Br2A 104.0(3) . . ? Br1A C5A Br2A 111.0(2) . . ? O6A C6A N1A 123.1(5) . . ? O6A C6A C5A 122.4(5) . . ? N1A C6A C5A 114.5(5) . . ? C4B N1B C2B 126.5(5) . . ? C6B N3B C2B 124.3(5) . . ? O2B C2B N1B 121.4(5) . . ? O2B C2B N3B 121.2(6) . . ? N1B C2B N3B 117.4(5) . . ? O4B C4B N1B 122.0(5) . . ? O4B C4B C5B 123.8(5) . . ? N1B C4B C5B 114.0(5) . . ? C6B C5B C4B 114.3(4) . . ? C6B C5B Br1B 110.9(3) . . ? C4B C5B Br1B 111.2(4) . . ? C6B C5B Br2B 104.7(3) . . ? C4B C5B Br2B 105.4(3) . . ? Br1B C5B Br2B 109.9(3) . . ? O6B C6B N3B 121.3(6) . . ? O6B C6B C5B 122.6(5) . . ? N3B C6B C5B 115.9(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 N1A H1A O2A 0.88(2) 1.97(2) 2.840(6) 168(5) 3_666 N3A H3A O4B 0.87(2) 2.02(4) 2.789(6) 146(5) . N1B H1B O4A 0.89(2) 1.97(2) 2.860(6) 178(6) 4_575 N3B H3B O2B 0.88(2) 1.94(2) 2.820(7) 173(6) 3_565 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.733 _refine_diff_density_min -0.485 _refine_diff_density_rms 0.136