# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_am27m _database_code_depnum_ccdc_archive 'CCDC 887818' #TrackingRef 'web_deposit_cif_file_0_B.Sridhar_1340105588.am27mf.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Cytosinium-2,5-dihydroxybenzoate _chemical_melting_point ? _chemical_formula_moiety 'C4 H6 N3 O +, C7 H5 O4 -' _chemical_formula_sum 'C11 H11 N3 O5' _chemical_formula_weight 265.23 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 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 10.1137(8) _cell_length_b 8.5120(7) _cell_length_c 13.9992(12) _cell_angle_alpha 90.00 _cell_angle_beta 110.610(1) _cell_angle_gamma 90.00 _cell_volume 1128.03(16) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 4906 _cell_measurement_theta_min 2.85 _cell_measurement_theta_max 27.94 _exptl_crystal_description Needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.562 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.126 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(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 'CCD Area Detector' _diffrn_measurement_device 'Bruker SMART APEX CCD area-detector' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10488 _diffrn_reflns_av_R_equivalents 0.0216 _diffrn_reflns_av_sigmaI/netI 0.0156 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1981 _reflns_number_gt 1821 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SAINT (Bruker, 2001)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL/PC (Sheldrick, 1990)' _computing_publication_material SHELXL97 _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^)+(0.0468P)^2^+0.2950P] 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 1981 _refine_ls_number_parameters 196 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0374 _refine_ls_R_factor_gt 0.0347 _refine_ls_wR_factor_ref 0.0926 _refine_ls_wR_factor_gt 0.0906 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.087 _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 C2 C 0.67894(14) 0.70848(17) 0.22160(10) 0.0324(3) Uani 1 1 d . . . C4 C 0.53055(14) 0.74251(16) 0.04467(10) 0.0296(3) Uani 1 1 d . . . C5 C 0.44874(15) 0.85430(17) 0.07418(11) 0.0354(3) Uani 1 1 d . . . H5 H 0.3720 0.9034 0.0259 0.042 Uiso 1 1 calc R . . C6 C 0.48514(15) 0.88720(18) 0.17356(12) 0.0385(4) Uani 1 1 d . . . H6 H 0.4332 0.9616 0.1940 0.046 Uiso 1 1 calc R . . N1 N 0.59548(13) 0.81548(15) 0.24542(9) 0.0370(3) Uani 1 1 d . . . H1N H 0.6266(18) 0.846(2) 0.3136(15) 0.055(5) Uiso 1 1 d . . . N3 N 0.64110(12) 0.67476(14) 0.11925(8) 0.0313(3) Uani 1 1 d . . . H3N H 0.6994(18) 0.603(2) 0.1019(13) 0.050(5) Uiso 1 1 d . . . N7 N 0.50546(13) 0.70166(16) -0.04993(9) 0.0373(3) Uani 1 1 d . . . H7N H 0.5686(19) 0.637(2) -0.0650(13) 0.049(5) Uiso 1 1 d . . . H8N H 0.431(2) 0.751(2) -0.1012(15) 0.057(5) Uiso 1 1 d . . . O8 O 0.78062(11) 0.64586(14) 0.28546(8) 0.0454(3) Uani 1 1 d . . . C11 C 0.78618(14) 0.43265(15) -0.02510(10) 0.0292(3) Uani 1 1 d . . . C12 C 0.88469(14) 0.32949(15) -0.05461(10) 0.0290(3) Uani 1 1 d . . . C13 C 1.00288(14) 0.26331(16) 0.01956(10) 0.0303(3) Uani 1 1 d . . . H13 H 1.0203 0.2845 0.0881 0.036 Uiso 1 1 calc R . . C14 C 1.09412(14) 0.16731(16) -0.00687(11) 0.0332(3) Uani 1 1 d . . . C15 C 1.06815(16) 0.13515(18) -0.10915(11) 0.0386(3) Uani 1 1 d . . . H15 H 1.1286 0.0692 -0.1275 0.046 Uiso 1 1 calc R . . C16 C 0.95317(16) 0.20072(19) -0.18331(11) 0.0407(4) Uani 1 1 d . . . H16 H 0.9370 0.1797 -0.2517 0.049 Uiso 1 1 calc R . . C17 C 0.86132(15) 0.29770(17) -0.15721(10) 0.0351(3) Uani 1 1 d . . . O9 O 0.80438(10) 0.45369(12) 0.06747(7) 0.0354(3) Uani 1 1 d . . . O10 O 0.68513(11) 0.49517(13) -0.09647(7) 0.0418(3) Uani 1 1 d . . . O18 O 1.21179(11) 0.10183(14) 0.06314(9) 0.0475(3) Uani 1 1 d . . . H180 H 1.218(2) 0.121(3) 0.1267(18) 0.071(6) Uiso 1 1 d . . . O19 O 0.74826(13) 0.35999(16) -0.23376(8) 0.0537(3) Uani 1 1 d . . . H190 H 0.705(2) 0.423(3) -0.1993(18) 0.084(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 C2 0.0305(7) 0.0360(7) 0.0280(7) -0.0027(6) 0.0069(6) -0.0025(6) C4 0.0259(6) 0.0325(7) 0.0286(7) 0.0007(5) 0.0071(5) -0.0022(5) C5 0.0312(7) 0.0370(8) 0.0353(8) 0.0008(6) 0.0082(6) 0.0055(6) C6 0.0379(8) 0.0363(8) 0.0428(8) -0.0051(6) 0.0161(7) 0.0042(6) N1 0.0398(7) 0.0412(7) 0.0291(6) -0.0069(5) 0.0111(5) 0.0007(5) N3 0.0283(6) 0.0368(7) 0.0272(6) -0.0037(5) 0.0077(5) 0.0034(5) N7 0.0338(7) 0.0476(7) 0.0272(6) -0.0007(5) 0.0066(5) 0.0075(6) O8 0.0413(6) 0.0561(7) 0.0292(5) -0.0026(5) 0.0005(5) 0.0105(5) C11 0.0310(7) 0.0311(7) 0.0261(7) 0.0027(5) 0.0107(6) -0.0005(5) C12 0.0318(7) 0.0290(7) 0.0276(7) 0.0002(5) 0.0121(6) -0.0024(5) C13 0.0328(7) 0.0349(7) 0.0242(7) -0.0009(5) 0.0113(6) -0.0004(6) C14 0.0318(7) 0.0343(7) 0.0344(7) 0.0003(6) 0.0127(6) 0.0008(6) C15 0.0417(8) 0.0382(8) 0.0417(8) -0.0061(6) 0.0219(7) 0.0012(6) C16 0.0501(9) 0.0479(9) 0.0271(7) -0.0080(6) 0.0171(7) -0.0009(7) C17 0.0374(8) 0.0407(8) 0.0257(7) -0.0003(6) 0.0093(6) -0.0011(6) O9 0.0396(6) 0.0430(6) 0.0255(5) 0.0033(4) 0.0138(4) 0.0101(4) O10 0.0422(6) 0.0517(7) 0.0287(5) 0.0051(4) 0.0092(4) 0.0161(5) O18 0.0400(6) 0.0608(7) 0.0401(7) 0.0011(5) 0.0122(5) 0.0193(5) O19 0.0564(7) 0.0745(9) 0.0239(6) -0.0001(5) 0.0063(5) 0.0214(6) _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 C2 O8 1.2222(17) . ? C2 N1 1.3606(18) . ? C2 N3 1.3769(17) . ? C4 N7 1.3049(18) . ? C4 N3 1.3605(17) . ? C4 C5 1.4146(19) . ? C5 C6 1.338(2) . ? C5 H5 0.9300 . ? C6 N1 1.3564(19) . ? C6 H6 0.9300 . ? N1 H1N 0.930(19) . ? N3 H3N 0.936(19) . ? N7 H7N 0.923(19) . ? N7 H8N 0.933(19) . ? C11 O9 1.2560(16) . ? C11 O10 1.2677(16) . ? C11 C12 1.4913(18) . ? C12 C13 1.3966(18) . ? C12 C17 1.3976(19) . ? C13 C14 1.3771(19) . ? C13 H13 0.9300 . ? C14 O18 1.3661(17) . ? C14 C15 1.389(2) . ? C15 C16 1.375(2) . ? C15 H15 0.9300 . ? C16 C17 1.385(2) . ? C16 H16 0.9300 . ? C17 O19 1.3689(17) . ? O18 H180 0.89(2) . ? O19 H190 0.93(2) . ? 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 O8 C2 N1 123.20(12) . . ? O8 C2 N3 121.63(13) . . ? N1 C2 N3 115.18(12) . . ? N7 C4 N3 118.66(13) . . ? N7 C4 C5 123.42(13) . . ? N3 C4 C5 117.92(12) . . ? C6 C5 C4 118.00(13) . . ? C6 C5 H5 121.0 . . ? C4 C5 H5 121.0 . . ? C5 C6 N1 122.05(13) . . ? C5 C6 H6 119.0 . . ? N1 C6 H6 119.0 . . ? C6 N1 C2 122.61(12) . . ? C6 N1 H1N 122.0(11) . . ? C2 N1 H1N 115.0(11) . . ? C4 N3 C2 124.23(12) . . ? C4 N3 H3N 119.9(10) . . ? C2 N3 H3N 115.8(11) . . ? C4 N7 H7N 119.2(11) . . ? C4 N7 H8N 118.5(11) . . ? H7N N7 H8N 121.7(16) . . ? O9 C11 O10 122.55(12) . . ? O9 C11 C12 120.01(12) . . ? O10 C11 C12 117.43(11) . . ? C13 C12 C17 118.48(12) . . ? C13 C12 C11 120.80(11) . . ? C17 C12 C11 120.72(12) . . ? C14 C13 C12 121.24(12) . . ? C14 C13 H13 119.4 . . ? C12 C13 H13 119.4 . . ? O18 C14 C13 123.10(12) . . ? O18 C14 C15 117.39(12) . . ? C13 C14 C15 119.50(13) . . ? C16 C15 C14 120.07(13) . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? C15 C16 C17 120.68(13) . . ? C15 C16 H16 119.7 . . ? C17 C16 H16 119.7 . . ? O19 C17 C16 118.52(12) . . ? O19 C17 C12 121.47(13) . . ? C16 C17 C12 120.01(13) . . ? C14 O18 H180 112.5(14) . . ? C17 O19 H190 103.6(14) . . ? 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 N7 C4 C5 C6 -179.67(14) . . . . ? N3 C4 C5 C6 0.2(2) . . . . ? C4 C5 C6 N1 -0.9(2) . . . . ? C5 C6 N1 C2 1.7(2) . . . . ? O8 C2 N1 C6 178.22(14) . . . . ? N3 C2 N1 C6 -1.7(2) . . . . ? N7 C4 N3 C2 179.59(13) . . . . ? C5 C4 N3 C2 -0.3(2) . . . . ? O8 C2 N3 C4 -178.91(13) . . . . ? N1 C2 N3 C4 1.0(2) . . . . ? O9 C11 C12 C13 -4.10(19) . . . . ? O10 C11 C12 C13 176.49(12) . . . . ? O9 C11 C12 C17 176.34(12) . . . . ? O10 C11 C12 C17 -3.07(19) . . . . ? C17 C12 C13 C14 -0.7(2) . . . . ? C11 C12 C13 C14 179.70(12) . . . . ? C12 C13 C14 O18 179.16(13) . . . . ? C12 C13 C14 C15 -0.2(2) . . . . ? O18 C14 C15 C16 -178.46(13) . . . . ? C13 C14 C15 C16 0.9(2) . . . . ? C14 C15 C16 C17 -0.7(2) . . . . ? C15 C16 C17 O19 -179.90(14) . . . . ? C15 C16 C17 C12 -0.2(2) . . . . ? C13 C12 C17 O19 -179.38(13) . . . . ? C11 C12 C17 O19 0.2(2) . . . . ? C13 C12 C17 C16 0.9(2) . . . . ? C11 C12 C17 C16 -179.51(13) . . . . ? 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 H1N O9 0.930(19) 1.812(19) 2.721(2) 165(2) 2_655 N3 H3N O9 0.936(19) 1.829(19) 2.763(2) 176(2) . N7 H7N O10 0.923(19) 1.84(2) 2.766(2) 176(2) . N7 H8N O8 0.933(19) 1.98(2) 2.911(2) 177(2) 4_575 O18 H180 O19 0.89(2) 1.87(2) 2.755(2) 173(2) 4_666 O19 H190 O10 0.93(2) 1.64(3) 2.508(2) 154(2) . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.199 _refine_diff_density_min -0.154 _refine_diff_density_rms 0.038 data_am81m _database_code_depnum_ccdc_archive 'CCDC 887819' #TrackingRef 'web_deposit_cif_file_2_B.Sridhar_1340105588.am81mf.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Cytosinium-3,5-dinitrobenzoate trihydrate' _chemical_melting_point ? _chemical_formula_moiety 'C4 H6 N3 O +, C7 H3 N2 O6 -, 3(H2 O)' _chemical_formula_sum 'C11 H15 N5 O10' _chemical_formula_weight 377.28 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 'P 21/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 5.0257(3) _cell_length_b 24.5327(15) _cell_length_c 13.1664(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.462(1) _cell_angle_gamma 90.00 _cell_volume 1623.29(17) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 4548 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 27.10 _exptl_crystal_description Plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.544 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.138 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(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 'CCD Area Detector' _diffrn_measurement_device 'Bruker SMART APEX CCD area-detector' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15406 _diffrn_reflns_av_R_equivalents 0.0291 _diffrn_reflns_av_sigmaI/netI 0.0208 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2841 _reflns_number_gt 2619 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SAINT (Bruker, 2001)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL/PC (Sheldrick, 1990)' _computing_publication_material SHELXL97 _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^)+(0.0398P)^2^+1.2265P] 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 2841 _refine_ls_number_parameters 275 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0702 _refine_ls_R_factor_gt 0.0647 _refine_ls_wR_factor_ref 0.1338 _refine_ls_wR_factor_gt 0.1312 _refine_ls_goodness_of_fit_ref 1.248 _refine_ls_restrained_S_all 1.248 _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 C2 C 0.4835(5) 0.67897(11) 0.1246(2) 0.0396(6) Uani 1 1 d . . . C4 C 0.1254(5) 0.65276(11) 0.2311(2) 0.0372(6) Uani 1 1 d . . . H4 H -0.0085 0.6277 0.2446 0.045 Uiso 1 1 calc R . . C5 C 0.1545(5) 0.69615(11) 0.2916(2) 0.0376(6) Uani 1 1 d . . . H5 H 0.0401 0.7019 0.3458 0.045 Uiso 1 1 calc R . . C6 C 0.3637(5) 0.73317(10) 0.27141(19) 0.0320(6) Uani 1 1 d . . . N1 N 0.5135(4) 0.72344(9) 0.18795(16) 0.0348(5) Uani 1 1 d . . . H1N H 0.636(6) 0.7471(11) 0.174(2) 0.035(7) Uiso 1 1 d . . . N3 N 0.2853(5) 0.64450(10) 0.15087(19) 0.0399(6) Uani 1 1 d . . . H3N H 0.265(5) 0.6168(12) 0.116(2) 0.038(8) Uiso 1 1 d . . . N7 N 0.4181(5) 0.77520(10) 0.32825(18) 0.0399(6) Uani 1 1 d . . . H7N H 0.557(7) 0.7994(13) 0.313(2) 0.057(9) Uiso 1 1 d . . . H8N H 0.320(6) 0.7809(12) 0.385(2) 0.050(9) Uiso 1 1 d . . . O8 O 0.6266(4) 0.67098(9) 0.05207(17) 0.0600(6) Uani 1 1 d . . . C11 C 0.9446(5) 0.84173(10) 0.2036(2) 0.0340(6) Uani 1 1 d . . . C12 C 1.1608(5) 0.88081(10) 0.16888(19) 0.0326(6) Uani 1 1 d . . . C13 C 1.3163(5) 0.86831(11) 0.08513(19) 0.0350(6) Uani 1 1 d . . . H13 H 1.2904 0.8358 0.0502 0.042 Uiso 1 1 calc R . . C14 C 1.5088(5) 0.90447(11) 0.05446(19) 0.0359(6) Uani 1 1 d . . . C15 C 1.5556(5) 0.95295(11) 0.1031(2) 0.0394(6) Uani 1 1 d . . . H15 H 1.6873 0.9768 0.0816 0.047 Uiso 1 1 calc R . . C16 C 1.3980(5) 0.96452(11) 0.1853(2) 0.0382(6) Uani 1 1 d . . . C17 C 1.2038(5) 0.92991(10) 0.2190(2) 0.0352(6) Uani 1 1 d . . . H17 H 1.1017 0.9392 0.2750 0.042 Uiso 1 1 calc R . . N18 N 1.6746(5) 0.89051(11) -0.03459(19) 0.0481(6) Uani 1 1 d . . . N21 N 1.4439(6) 1.01636(10) 0.2388(2) 0.0547(7) Uani 1 1 d . . . O9 O 0.8208(4) 0.85363(8) 0.28170(15) 0.0479(5) Uani 1 1 d . . . O10 O 0.9061(4) 0.80055(8) 0.14989(15) 0.0459(5) Uani 1 1 d . . . O19 O 1.6364(5) 0.84701(11) -0.07546(18) 0.0690(7) Uani 1 1 d . . . O20 O 1.8421(5) 0.92382(11) -0.06048(18) 0.0718(7) Uani 1 1 d . . . O22 O 1.6353(6) 1.04310(11) 0.2137(2) 0.0960(10) Uani 1 1 d . . . O23 O 1.2885(5) 1.02985(9) 0.3042(2) 0.0709(7) Uani 1 1 d . . . O1W O 1.0581(5) 0.73242(11) -0.00810(19) 0.0592(6) Uani 1 1 d . . . H1W H 0.931(8) 0.7089(17) -0.003(3) 0.086(14) Uiso 1 1 d . . . H2W H 1.034(8) 0.7575(19) 0.036(3) 0.095(15) Uiso 1 1 d . . . O2W O 0.2188(6) 0.55371(10) 0.02682(19) 0.0561(6) Uani 1 1 d . . . H3W H 0.231(8) 0.5235(19) 0.055(3) 0.090(15) Uiso 1 1 d . . . H4W H 0.067(9) 0.5563(18) -0.007(3) 0.092(15) Uiso 1 1 d . . . O3W O 0.2674(5) 0.43915(10) 0.0821(2) 0.0606(7) Uani 1 1 d . . . H5W H 0.239(8) 0.4114(17) 0.118(3) 0.080(13) Uiso 1 1 d . . . H6W H 0.403(9) 0.4329(18) 0.049(3) 0.093(15) 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 C2 0.0384(15) 0.0385(15) 0.0420(16) -0.0024(12) 0.0066(13) -0.0038(12) C4 0.0346(14) 0.0340(14) 0.0431(16) 0.0093(12) 0.0048(12) -0.0050(11) C5 0.0357(14) 0.0409(15) 0.0362(14) 0.0071(12) 0.0071(11) -0.0031(12) C6 0.0309(13) 0.0331(14) 0.0318(13) 0.0046(11) 0.0017(11) 0.0006(11) N1 0.0323(12) 0.0342(12) 0.0382(13) -0.0006(10) 0.0091(10) -0.0077(10) N3 0.0453(14) 0.0311(13) 0.0434(14) -0.0038(11) 0.0057(11) -0.0058(11) N7 0.0427(14) 0.0415(13) 0.0357(13) -0.0062(11) 0.0118(11) -0.0099(11) O8 0.0582(13) 0.0624(14) 0.0599(14) -0.0215(11) 0.0280(11) -0.0142(11) C11 0.0321(14) 0.0324(14) 0.0375(14) 0.0007(12) 0.0029(11) -0.0003(11) C12 0.0291(13) 0.0344(14) 0.0344(14) 0.0022(11) -0.0006(11) 0.0017(11) C13 0.0337(14) 0.0345(14) 0.0367(14) -0.0032(11) -0.0003(11) 0.0005(11) C14 0.0324(14) 0.0419(15) 0.0334(14) 0.0025(11) 0.0035(11) 0.0034(11) C15 0.0353(15) 0.0405(15) 0.0424(16) 0.0095(12) 0.0012(12) -0.0074(12) C16 0.0400(15) 0.0324(14) 0.0422(16) 0.0000(12) -0.0017(12) -0.0029(12) C17 0.0368(14) 0.0345(14) 0.0343(14) -0.0010(11) 0.0046(11) -0.0012(11) N18 0.0384(14) 0.0638(17) 0.0423(14) 0.0003(13) 0.0072(11) 0.0003(13) N21 0.0681(18) 0.0388(14) 0.0574(17) -0.0081(12) 0.0023(14) -0.0152(13) O9 0.0505(12) 0.0453(11) 0.0481(12) -0.0121(9) 0.0209(10) -0.0138(9) O10 0.0485(12) 0.0396(11) 0.0499(12) -0.0124(9) 0.0134(9) -0.0157(9) O19 0.0641(15) 0.0799(18) 0.0635(15) -0.0281(13) 0.0235(12) -0.0066(13) O20 0.0614(15) 0.0886(18) 0.0658(15) 0.0043(13) 0.0312(12) -0.0189(14) O22 0.107(2) 0.0690(17) 0.112(2) -0.0310(16) 0.0333(18) -0.0580(17) O23 0.0874(18) 0.0511(14) 0.0746(17) -0.0232(12) 0.0189(14) -0.0066(13) O1W 0.0660(16) 0.0540(15) 0.0581(15) -0.0055(12) 0.0293(12) -0.0097(12) O2W 0.0715(17) 0.0407(13) 0.0561(14) -0.0035(11) -0.0048(12) -0.0120(12) O3W 0.0693(17) 0.0511(14) 0.0618(15) 0.0151(12) 0.0226(13) 0.0150(12) _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 C2 O8 1.216(3) . ? C2 N3 1.354(3) . ? C2 N1 1.381(3) . ? C4 C5 1.338(4) . ? C4 N3 1.347(3) . ? C4 H4 0.9300 . ? C5 C6 1.416(4) . ? C5 H5 0.9300 . ? C6 N7 1.302(3) . ? C6 N1 1.358(3) . ? N1 H1N 0.87(3) . ? N3 H3N 0.83(3) . ? N7 H7N 0.94(3) . ? N7 H8N 0.91(3) . ? C11 O9 1.241(3) . ? C11 O10 1.247(3) . ? C11 C12 1.522(3) . ? C12 C17 1.390(4) . ? C12 C13 1.391(4) . ? C13 C14 1.376(4) . ? C13 H13 0.9300 . ? C14 C15 1.370(4) . ? C14 N18 1.484(3) . ? C15 C16 1.376(4) . ? C15 H15 0.9300 . ? C16 C17 1.371(4) . ? C16 N21 1.471(4) . ? C17 H17 0.9300 . ? N18 O19 1.210(3) . ? N18 O20 1.224(3) . ? N21 O22 1.213(3) . ? N21 O23 1.213(3) . ? O1W H1W 0.86(4) . ? O1W H2W 0.86(5) . ? O2W H3W 0.83(5) . ? O2W H4W 0.88(5) . ? O3W H5W 0.85(4) . ? O3W H6W 0.83(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 O8 C2 N3 122.7(3) . . ? O8 C2 N1 122.7(2) . . ? N3 C2 N1 114.6(2) . . ? C5 C4 N3 121.6(2) . . ? C5 C4 H4 119.2 . . ? N3 C4 H4 119.2 . . ? C4 C5 C6 118.4(2) . . ? C4 C5 H5 120.8 . . ? C6 C5 H5 120.8 . . ? N7 C6 N1 119.3(2) . . ? N7 C6 C5 123.5(2) . . ? N1 C6 C5 117.2(2) . . ? C6 N1 C2 124.7(2) . . ? C6 N1 H1N 116.7(18) . . ? C2 N1 H1N 118.6(18) . . ? C4 N3 C2 123.4(2) . . ? C4 N3 H3N 119(2) . . ? C2 N3 H3N 117(2) . . ? C6 N7 H7N 122(2) . . ? C6 N7 H8N 119(2) . . ? H7N N7 H8N 119(3) . . ? O9 C11 O10 125.7(2) . . ? O9 C11 C12 117.7(2) . . ? O10 C11 C12 116.6(2) . . ? C17 C12 C13 118.8(2) . . ? C17 C12 C11 120.8(2) . . ? C13 C12 C11 120.4(2) . . ? C14 C13 C12 119.4(2) . . ? C14 C13 H13 120.3 . . ? C12 C13 H13 120.3 . . ? C15 C14 C13 122.8(2) . . ? C15 C14 N18 118.3(2) . . ? C13 C14 N18 118.9(2) . . ? C14 C15 C16 116.7(2) . . ? C14 C15 H15 121.7 . . ? C16 C15 H15 121.7 . . ? C17 C16 C15 122.9(3) . . ? C17 C16 N21 119.3(3) . . ? C15 C16 N21 117.8(2) . . ? C16 C17 C12 119.4(2) . . ? C16 C17 H17 120.3 . . ? C12 C17 H17 120.3 . . ? O19 N18 O20 124.9(3) . . ? O19 N18 C14 117.9(2) . . ? O20 N18 C14 117.2(3) . . ? O22 N21 O23 124.2(3) . . ? O22 N21 C16 117.3(3) . . ? O23 N21 C16 118.5(3) . . ? H1W O1W H2W 109(4) . . ? H3W O2W H4W 110(4) . . ? H5W O3W H6W 107(4) . . ? 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 N3 C4 C5 C6 -1.6(4) . . . . ? C4 C5 C6 N7 -176.6(3) . . . . ? C4 C5 C6 N1 3.3(4) . . . . ? N7 C6 N1 C2 176.8(3) . . . . ? C5 C6 N1 C2 -3.0(4) . . . . ? O8 C2 N1 C6 -178.0(3) . . . . ? N3 C2 N1 C6 0.9(4) . . . . ? C5 C4 N3 C2 -0.7(4) . . . . ? O8 C2 N3 C4 179.9(3) . . . . ? N1 C2 N3 C4 1.1(4) . . . . ? O9 C11 C12 C17 -4.6(4) . . . . ? O10 C11 C12 C17 174.8(2) . . . . ? O9 C11 C12 C13 176.5(2) . . . . ? O10 C11 C12 C13 -4.1(4) . . . . ? C17 C12 C13 C14 0.4(4) . . . . ? C11 C12 C13 C14 179.3(2) . . . . ? C12 C13 C14 C15 0.0(4) . . . . ? C12 C13 C14 N18 179.6(2) . . . . ? C13 C14 C15 C16 -0.4(4) . . . . ? N18 C14 C15 C16 180.0(2) . . . . ? C14 C15 C16 C17 0.5(4) . . . . ? C14 C15 C16 N21 -180.0(2) . . . . ? C15 C16 C17 C12 -0.1(4) . . . . ? N21 C16 C17 C12 -179.7(2) . . . . ? C13 C12 C17 C16 -0.3(4) . . . . ? C11 C12 C17 C16 -179.3(2) . . . . ? C15 C14 N18 O19 178.2(3) . . . . ? C13 C14 N18 O19 -1.5(4) . . . . ? C15 C14 N18 O20 -1.1(4) . . . . ? C13 C14 N18 O20 179.3(3) . . . . ? C17 C16 N21 O22 172.3(3) . . . . ? C15 C16 N21 O22 -7.3(4) . . . . ? C17 C16 N21 O23 -8.3(4) . . . . ? C15 C16 N21 O23 172.1(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 N1 H1N O10 0.87(3) 1.92(3) 2.782(3) 178(3) . N3 H3N O2W 0.83(3) 1.96(3) 2.780(3) 177(3) . N7 H7N O9 0.94(3) 1.93(3) 2.862(3) 175(3) . N7 H8N O1W 0.91(3) 1.96(3) 2.831(3) 159(3) 4_476 O1W H1W O8 0.86(4) 1.94(4) 2.762(3) 159(4) . O1W H2W O10 0.86(5) 1.94(5) 2.780(3) 164(4) . O2W H3W O3W 0.83(5) 2.11(5) 2.913(4) 163(4) . O2W H4W O3W 0.88(5) 1.95(5) 2.828(4) 179(4) 3_565 O3W H5W O9 0.85(4) 1.96(4) 2.798(3) 172(4) 2_645 O3W H6W O2W 0.83(5) 2.18(5) 2.969(4) 160(4) 3_665 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.212 _refine_diff_density_min -0.185 _refine_diff_density_rms 0.044 data_ai26 _database_code_depnum_ccdc_archive 'CCDC 887820' #TrackingRef 'web_deposit_cif_file_4_B.Sridhar_1340105588.ai26f.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; Cytosinium 4-hydroxyphenylacetate cytosine monohydrate ; _chemical_melting_point ? _chemical_formula_moiety 'C4 H6 N3 O +, C8 H7 O3 -, C4 H5 N3 O, H2 O' _chemical_formula_sum 'C16 H20 N6 O6' _chemical_formula_weight 392.38 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 orthorhombic _symmetry_space_group_name_H-M 'P b c n' _symmetry_space_group_name_Hall '-P 2n 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 14.9164(10) _cell_length_b 12.3456(8) _cell_length_c 19.9754(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3678.5(4) _cell_formula_units_Z 8 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 7638 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 27.92 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.417 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1648 _exptl_absorpt_coefficient_mu 0.111 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(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 'CCD Area Detector' _diffrn_measurement_device 'Bruker SMART APEX CCD area-detector' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 33286 _diffrn_reflns_av_R_equivalents 0.0189 _diffrn_reflns_av_sigmaI/netI 0.0109 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3239 _reflns_number_gt 2896 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SAINT (Bruker, 2001)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL/PC (Sheldrick, 1990)' _computing_publication_material SHELXL97 _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^)+(0.0458P)^2^+0.9989P] 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 3239 _refine_ls_number_parameters 293 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0395 _refine_ls_R_factor_gt 0.0356 _refine_ls_wR_factor_ref 0.0965 _refine_ls_wR_factor_gt 0.0934 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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 C2A C 0.14876(10) 0.33574(12) 0.19821(7) 0.0486(3) Uani 1 1 d . . . C4A C 0.05431(10) 0.48795(11) 0.17321(7) 0.0473(3) Uani 1 1 d . . . C5A C 0.12670(11) 0.55960(13) 0.18562(8) 0.0564(4) Uani 1 1 d . . . H5A H 0.1198 0.6342 0.1814 0.068 Uiso 1 1 calc R . . C6A C 0.20525(11) 0.51609(14) 0.20355(8) 0.0578(4) Uani 1 1 d . . . H6A H 0.2536 0.5616 0.2119 0.069 Uiso 1 1 calc R . . N1A N 0.21640(9) 0.40795(12) 0.20994(7) 0.0567(3) Uani 1 1 d . . . H1A H 0.2717(14) 0.3793(16) 0.2233(10) 0.086(6) Uiso 1 1 d . . . N3A N 0.06795(8) 0.38059(10) 0.17964(6) 0.0468(3) Uani 1 1 d . . . H2A H 0.0243(14) 0.3309(17) 0.1701(11) 0.088(7) Uiso 1 1 d . . . N7A N -0.02632(9) 0.52064(12) 0.15605(8) 0.0586(4) Uani 1 1 d . . . H3A H -0.0760(13) 0.4696(16) 0.1473(10) 0.077(6) Uiso 1 1 d . . . H4A H -0.0388(11) 0.5915(16) 0.1507(9) 0.063(5) Uiso 1 1 d . . . O8A O 0.15845(7) 0.23781(9) 0.20409(6) 0.0608(3) Uani 1 1 d . . . C2B C -0.15543(10) 0.27961(12) 0.13526(7) 0.0486(3) Uani 1 1 d . . . C4B C -0.06293(10) 0.12805(12) 0.14884(8) 0.0493(3) Uani 1 1 d . . . C5B C -0.13696(11) 0.05752(13) 0.13897(9) 0.0591(4) Uani 1 1 d . . . H5B H -0.1298 -0.0173 0.1398 0.071 Uiso 1 1 calc R . . C6B C -0.21697(11) 0.10223(13) 0.12853(8) 0.0564(4) Uani 1 1 d . . . H6B H -0.2668 0.0581 0.1223 0.068 Uiso 1 1 calc R . . N1B N -0.22655(9) 0.21090(11) 0.12694(7) 0.0539(3) Uani 1 1 d . . . H1B H -0.2822(14) 0.2383(16) 0.1225(10) 0.080(6) Uiso 1 1 d . . . N3B N -0.07301(8) 0.23578(9) 0.14656(6) 0.0462(3) Uani 1 1 d . . . N7B N 0.01834(10) 0.09000(13) 0.16022(10) 0.0730(5) Uani 1 1 d . . . H2B H 0.0271(13) 0.0209(19) 0.1604(11) 0.086(7) Uiso 1 1 d . . . H3B H 0.0669(13) 0.1384(16) 0.1743(10) 0.077(6) Uiso 1 1 d . . . O8B O -0.16725(8) 0.37849(9) 0.13296(7) 0.0707(4) Uani 1 1 d . . . C11 C -0.02086(9) 0.79466(10) 0.09764(7) 0.0420(3) Uani 1 1 d . . . C12 C -0.02354(11) 0.78199(16) 0.02200(8) 0.0656(5) Uani 1 1 d . . . H12A H -0.0246 0.8535 0.0020 0.079 Uiso 1 1 calc R . . H12B H 0.0313 0.7468 0.0077 0.079 Uiso 1 1 calc R . . C13 C -0.10202(10) 0.71817(13) -0.00461(7) 0.0524(4) Uani 1 1 d . . . C14 C -0.17619(11) 0.76969(13) -0.03048(8) 0.0556(4) Uani 1 1 d . . . H14 H -0.1762 0.8448 -0.0341 0.067 Uiso 1 1 calc R . . C15 C -0.25079(10) 0.71195(12) -0.05114(8) 0.0530(4) Uani 1 1 d . . . H15 H -0.3002 0.7484 -0.0685 0.064 Uiso 1 1 calc R . . C16 C -0.25210(10) 0.60059(12) -0.04604(7) 0.0480(3) Uani 1 1 d . . . C17 C -0.17741(11) 0.54737(12) -0.02133(8) 0.0547(4) Uani 1 1 d . . . H17 H -0.1770 0.4722 -0.0184 0.066 Uiso 1 1 calc R . . C18 C -0.10371(10) 0.60617(14) -0.00110(8) 0.0564(4) Uani 1 1 d . . . H18 H -0.0538 0.5697 0.0153 0.068 Uiso 1 1 calc R . . O9 O 0.04136(7) 0.85125(9) 0.12113(5) 0.0582(3) Uani 1 1 d . . . O10 O -0.07876(7) 0.74920(8) 0.13323(5) 0.0524(3) Uani 1 1 d . . . O19 O -0.32384(8) 0.53954(9) -0.06491(7) 0.0655(3) Uani 1 1 d . . . H19O H -0.3662(14) 0.5829(18) -0.0773(11) 0.088(7) Uiso 1 1 d . . . O1W O 0.38436(9) 0.34531(15) 0.24470(8) 0.0860(5) Uani 1 1 d . . . H1W H 0.3994(15) 0.3142(18) 0.2782(12) 0.090(7) Uiso 1 1 d . . . H2W H 0.4177(16) 0.3393(19) 0.2120(13) 0.097(8) 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 C2A 0.0485(8) 0.0539(9) 0.0432(7) 0.0019(6) 0.0019(6) 0.0053(7) C4A 0.0507(8) 0.0442(8) 0.0469(8) -0.0005(6) 0.0036(6) 0.0014(6) C5A 0.0601(9) 0.0476(8) 0.0615(9) -0.0055(7) 0.0046(7) -0.0069(7) C6A 0.0545(9) 0.0638(10) 0.0552(9) -0.0087(7) 0.0014(7) -0.0125(8) N1A 0.0449(7) 0.0704(9) 0.0547(8) -0.0001(6) -0.0040(6) 0.0003(6) N3A 0.0455(6) 0.0438(7) 0.0510(7) 0.0015(5) -0.0013(5) 0.0013(5) N7A 0.0544(8) 0.0419(7) 0.0794(10) 0.0051(6) -0.0035(7) 0.0057(6) O8A 0.0562(6) 0.0558(7) 0.0704(7) 0.0084(5) -0.0031(5) 0.0123(5) C2B 0.0461(8) 0.0455(8) 0.0541(8) 0.0023(6) -0.0005(6) 0.0036(6) C4B 0.0469(8) 0.0434(8) 0.0575(9) 0.0021(6) 0.0040(6) 0.0033(6) C5B 0.0590(9) 0.0423(8) 0.0760(11) 0.0022(7) 0.0007(8) -0.0051(7) C6B 0.0529(9) 0.0550(9) 0.0615(9) 0.0022(7) -0.0020(7) -0.0111(7) N1B 0.0411(7) 0.0590(8) 0.0616(8) 0.0034(6) -0.0054(6) 0.0018(6) N3B 0.0422(6) 0.0408(6) 0.0556(7) 0.0024(5) 0.0018(5) 0.0031(5) N7B 0.0520(8) 0.0430(8) 0.1238(14) 0.0019(8) -0.0059(8) 0.0085(7) O8B 0.0556(6) 0.0469(6) 0.1096(10) 0.0048(6) -0.0122(6) 0.0101(5) C11 0.0367(7) 0.0390(7) 0.0502(8) -0.0017(6) 0.0006(6) 0.0014(6) C12 0.0590(10) 0.0873(12) 0.0505(9) -0.0055(8) 0.0047(7) -0.0228(9) C13 0.0508(8) 0.0644(10) 0.0419(7) -0.0060(7) 0.0023(6) -0.0082(7) C14 0.0648(10) 0.0456(8) 0.0565(9) 0.0013(7) -0.0005(7) -0.0049(7) C15 0.0519(8) 0.0478(8) 0.0592(9) 0.0047(7) -0.0072(7) 0.0058(7) C16 0.0483(8) 0.0461(8) 0.0496(8) -0.0006(6) -0.0065(6) -0.0004(6) C17 0.0609(9) 0.0438(8) 0.0593(9) -0.0033(7) -0.0109(7) 0.0074(7) C18 0.0485(8) 0.0675(10) 0.0533(9) -0.0070(7) -0.0095(7) 0.0115(7) O9 0.0466(6) 0.0734(7) 0.0546(6) -0.0060(5) 0.0002(5) -0.0163(5) O10 0.0498(6) 0.0569(6) 0.0504(6) -0.0021(5) 0.0065(5) -0.0115(5) O19 0.0566(7) 0.0506(6) 0.0895(9) 0.0038(6) -0.0222(6) -0.0054(5) O1W 0.0567(8) 0.1444(15) 0.0569(8) 0.0135(9) 0.0012(7) 0.0331(8) _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 C2A O8A 1.2234(18) . ? C2A N1A 1.367(2) . ? C2A N3A 1.3772(19) . ? C4A N7A 1.3141(19) . ? C4A N3A 1.3471(19) . ? C4A C5A 1.418(2) . ? C5A C6A 1.338(2) . ? C5A H5A 0.9300 . ? C6A N1A 1.351(2) . ? C6A H6A 0.9300 . ? N1A H1A 0.94(2) . ? N3A H2A 0.91(2) . ? N7A H3A 0.99(2) . ? N7A H4A 0.901(19) . ? C2B O8B 1.2343(18) . ? C2B N3B 1.3619(18) . ? C2B N1B 1.3685(19) . ? C4B N7B 1.320(2) . ? C4B N3B 1.3392(18) . ? C4B C5B 1.420(2) . ? C5B C6B 1.331(2) . ? C5B H5B 0.9300 . ? C6B N1B 1.350(2) . ? C6B H6B 0.9300 . ? N1B H1B 0.90(2) . ? N7B H2B 0.86(2) . ? N7B H3B 0.98(2) . ? C11 O10 1.2516(16) . ? C11 O9 1.2529(16) . ? C11 C12 1.519(2) . ? C12 C13 1.508(2) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.377(2) . ? C13 C18 1.385(2) . ? C14 C15 1.384(2) . ? C14 H14 0.9300 . ? C15 C16 1.379(2) . ? C15 H15 0.9300 . ? C16 O19 1.3621(18) . ? C16 C17 1.384(2) . ? C17 C18 1.378(2) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? O19 H19O 0.86(2) . ? O1W H1W 0.80(2) . ? O1W H2W 0.82(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 O8A C2A N1A 122.74(14) . . ? O8A C2A N3A 121.78(14) . . ? N1A C2A N3A 115.47(14) . . ? N7A C4A N3A 117.73(14) . . ? N7A C4A C5A 123.44(14) . . ? N3A C4A C5A 118.83(14) . . ? C6A C5A C4A 117.61(15) . . ? C6A C5A H5A 121.2 . . ? C4A C5A H5A 121.2 . . ? C5A C6A N1A 121.98(15) . . ? C5A C6A H6A 119.0 . . ? N1A C6A H6A 119.0 . . ? C6A N1A C2A 122.51(14) . . ? C6A N1A H1A 120.6(12) . . ? C2A N1A H1A 116.9(12) . . ? C4A N3A C2A 123.60(13) . . ? C4A N3A H2A 122.2(13) . . ? C2A N3A H2A 114.2(13) . . ? C4A N7A H3A 122.4(11) . . ? C4A N7A H4A 121.3(11) . . ? H3A N7A H4A 116.3(16) . . ? O8B C2B N3B 121.88(13) . . ? O8B C2B N1B 119.85(13) . . ? N3B C2B N1B 118.27(13) . . ? N7B C4B N3B 117.54(14) . . ? N7B C4B C5B 121.33(14) . . ? N3B C4B C5B 121.13(13) . . ? C6B C5B C4B 117.68(14) . . ? C6B C5B H5B 121.2 . . ? C4B C5B H5B 121.2 . . ? C5B C6B N1B 120.72(14) . . ? C5B C6B H6B 119.6 . . ? N1B C6B H6B 119.6 . . ? C6B N1B C2B 122.08(13) . . ? C6B N1B H1B 118.2(12) . . ? C2B N1B H1B 119.6(12) . . ? C4B N3B C2B 120.10(12) . . ? C4B N7B H2B 119.5(14) . . ? C4B N7B H3B 120.7(11) . . ? H2B N7B H3B 119.3(18) . . ? O10 C11 O9 123.27(13) . . ? O10 C11 C12 120.03(12) . . ? O9 C11 C12 116.70(12) . . ? C13 C12 C11 115.14(13) . . ? C13 C12 H12A 108.5 . . ? C11 C12 H12A 108.5 . . ? C13 C12 H12B 108.5 . . ? C11 C12 H12B 108.5 . . ? H12A C12 H12B 107.5 . . ? C14 C13 C18 117.76(14) . . ? C14 C13 C12 120.98(15) . . ? C18 C13 C12 121.20(15) . . ? C13 C14 C15 121.32(15) . . ? C13 C14 H14 119.3 . . ? C15 C14 H14 119.3 . . ? C16 C15 C14 120.19(14) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? O19 C16 C15 122.85(13) . . ? O19 C16 C17 117.93(13) . . ? C15 C16 C17 119.22(13) . . ? C18 C17 C16 119.77(14) . . ? C18 C17 H17 120.1 . . ? C16 C17 H17 120.1 . . ? C17 C18 C13 121.72(14) . . ? C17 C18 H18 119.1 . . ? C13 C18 H18 119.1 . . ? C16 O19 H19O 108.1(14) . . ? H1W O1W H2W 117(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 N7A C4A C5A C6A 179.19(15) . . . . ? N3A C4A C5A C6A -0.3(2) . . . . ? C4A C5A C6A N1A -0.1(2) . . . . ? C5A C6A N1A C2A 0.4(2) . . . . ? O8A C2A N1A C6A -179.81(14) . . . . ? N3A C2A N1A C6A -0.3(2) . . . . ? N7A C4A N3A C2A -179.08(14) . . . . ? C5A C4A N3A C2A 0.5(2) . . . . ? O8A C2A N3A C4A 179.36(14) . . . . ? N1A C2A N3A C4A -0.2(2) . . . . ? N7B C4B C5B C6B 179.24(17) . . . . ? N3B C4B C5B C6B -1.1(2) . . . . ? C4B C5B C6B N1B 0.5(2) . . . . ? C5B C6B N1B C2B 0.6(2) . . . . ? O8B C2B N1B C6B 179.49(15) . . . . ? N3B C2B N1B C6B -1.1(2) . . . . ? N7B C4B N3B C2B -179.73(15) . . . . ? C5B C4B N3B C2B 0.6(2) . . . . ? O8B C2B N3B C4B 179.86(15) . . . . ? N1B C2B N3B C4B 0.5(2) . . . . ? O10 C11 C12 C13 3.4(2) . . . . ? O9 C11 C12 C13 -176.98(14) . . . . ? C11 C12 C13 C14 99.50(19) . . . . ? C11 C12 C13 C18 -77.5(2) . . . . ? C18 C13 C14 C15 1.2(2) . . . . ? C12 C13 C14 C15 -175.91(14) . . . . ? C13 C14 C15 C16 0.1(2) . . . . ? C14 C15 C16 O19 179.33(14) . . . . ? C14 C15 C16 C17 -1.3(2) . . . . ? O19 C16 C17 C18 -179.39(14) . . . . ? C15 C16 C17 C18 1.2(2) . . . . ? C16 C17 C18 C13 0.1(2) . . . . ? C14 C13 C18 C17 -1.3(2) . . . . ? C12 C13 C18 C17 175.81(14) . . . . ? 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 O1W 0.94(2) 1.78(2) 2.712(2) 171(2) . N3A H2A N3B 0.91(2) 1.93(2) 2.838(2) 175(2) . N7A H3A O8B 0.99(2) 1.79(2) 2.777(2) 179(2) . N7A H4A O10 0.901(19) 2.066(19) 2.963(2) 174(2) . N1B H1B O10 0.90(2) 2.09(2) 2.945(2) 158(2) 8 N7B H2B O9 0.86(2) 2.25(2) 3.068(2) 159(2) 1_545 N7B H3B O8A 0.98(2) 1.93(2) 2.910(2) 177(2) . O19 H19O O9 0.86(2) 1.82(2) 2.669(2) 165(2) 4_465 O1W H1W O10 0.80(2) 1.97(3) 2.767(2) 171(2) 6_656 O1W H2W O9 0.82(3) 1.92(3) 2.707(2) 159(2) 8_655 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.232 _refine_diff_density_min -0.191 _refine_diff_density_rms 0.033 data_an57m _database_code_depnum_ccdc_archive 'CCDC 887821' #TrackingRef 'web_deposit_cif_file_6_B.Sridhar_1340105588.an57mf.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; Cytosinium para amino benzoate cytosine monohydrate ; _chemical_melting_point ? _chemical_formula_moiety 'C4 H6 N3 O +, C7 H6 N O2 -, C4 H5 N3 O, H2 O' _chemical_formula_sum 'C15 H19 N7 O5' _chemical_formula_weight 377.37 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 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 7.3666(3) _cell_length_b 6.4615(3) _cell_length_c 36.9629(16) _cell_angle_alpha 90.00 _cell_angle_beta 94.462(1) _cell_angle_gamma 90.00 _cell_volume 1754.08(13) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 7737 _cell_measurement_theta_min 2.79 _cell_measurement_theta_max 28.00 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.429 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 0.110 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(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 'CCD Area Detector' _diffrn_measurement_device 'Bruker SMART APEX CCD area-detector' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16058 _diffrn_reflns_av_R_equivalents 0.0292 _diffrn_reflns_av_sigmaI/netI 0.0214 _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 -43 _diffrn_reflns_limit_l_max 43 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3099 _reflns_number_gt 2849 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SAINT (Bruker, 2001)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL/PC (Sheldrick, 1990)' _computing_publication_material SHELXL97 _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^)+(0.0788P)^2^+0.6342P] 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 3099 _refine_ls_number_parameters 288 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0548 _refine_ls_R_factor_gt 0.0514 _refine_ls_wR_factor_ref 0.1450 _refine_ls_wR_factor_gt 0.1415 _refine_ls_goodness_of_fit_ref 1.117 _refine_ls_restrained_S_all 1.117 _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 C2A C 1.1011(2) 0.2315(2) 0.07140(5) 0.0289(4) Uani 1 1 d . . . C4A C 0.9636(3) 0.2233(3) 0.12734(5) 0.0378(4) Uani 1 1 d . . . H4A H 0.9762 0.2137 0.1525 0.045 Uiso 1 1 calc R . . C5A C 0.7983(3) 0.2471(3) 0.11028(5) 0.0365(4) Uani 1 1 d . . . H5A H 0.6950 0.2586 0.1231 0.044 Uiso 1 1 calc R . . C6A C 0.7866(2) 0.2540(2) 0.07169(5) 0.0314(4) Uani 1 1 d . . . N1A N 0.93564(19) 0.24880(19) 0.05307(4) 0.0290(3) Uani 1 1 d . . . H1N H 1.222(3) 0.177(4) 0.1192(6) 0.056(6) Uiso 1 1 d . . . N3A N 1.1128(2) 0.2132(2) 0.10832(4) 0.0362(4) Uani 1 1 d . . . N7A N 0.6274(2) 0.2657(3) 0.05277(6) 0.0488(5) Uani 1 1 d . . . H2N H 0.526(4) 0.260(3) 0.0637(7) 0.057(7) Uiso 1 1 d . . . H3N H 0.632(3) 0.267(3) 0.0303(8) 0.054(7) Uiso 1 1 d . . . O8A O 1.24356(16) 0.2283(2) 0.05531(4) 0.0406(4) Uani 1 1 d . . . C2B C 0.7626(2) 0.2576(2) -0.04335(5) 0.0306(4) Uani 1 1 d . . . C4B C 0.9203(2) 0.2614(2) -0.09678(5) 0.0325(4) Uani 1 1 d . . . H4B H 0.9137 0.2639 -0.1220 0.039 Uiso 1 1 calc R . . C5B C 1.0854(2) 0.2590(2) -0.07857(5) 0.0321(4) Uani 1 1 d . . . H5B H 1.1913 0.2605 -0.0907 0.039 Uiso 1 1 calc R . . C6B C 1.0918(2) 0.2539(2) -0.04019(5) 0.0289(4) Uani 1 1 d . . . N1B N 0.9318(2) 0.2550(2) -0.02450(4) 0.0296(4) Uani 1 1 d . . . H4N H 0.925(3) 0.251(3) -0.0029(7) 0.038(6) Uiso 1 1 d . . . N3B N 0.7627(2) 0.2604(2) -0.08005(4) 0.0328(4) Uani 1 1 d . . . H5N H 0.646(3) 0.253(3) -0.0945(7) 0.055(7) Uiso 1 1 d . . . N7B N 1.2428(2) 0.2485(3) -0.01933(5) 0.0390(4) Uani 1 1 d . . . H6N H 1.237(3) 0.243(3) 0.0029(7) 0.036(6) Uiso 1 1 d . . . H7N H 1.342(3) 0.250(3) -0.0277(7) 0.045(6) Uiso 1 1 d . . . O8B O 0.62379(17) 0.2573(2) -0.02724(4) 0.0423(4) Uani 1 1 d . . . C11 C 0.4654(2) 0.0924(3) -0.14872(5) 0.0360(4) Uani 1 1 d . . . C12 C 0.3092(2) 0.1006(3) -0.17696(4) 0.0352(4) Uani 1 1 d . . . C13 C 0.2845(3) -0.0478(3) -0.20415(5) 0.0453(5) Uani 1 1 d . . . H13 H 0.3705 -0.1522 -0.2056 0.054 Uiso 1 1 calc R . . C14 C 0.1345(3) -0.0426(4) -0.22898(5) 0.0516(5) Uani 1 1 d . . . H14 H 0.1211 -0.1434 -0.2470 0.062 Uiso 1 1 calc R . . C15 C 0.0043(3) 0.1101(4) -0.22748(5) 0.0489(5) Uani 1 1 d . . . C16 C 0.0276(3) 0.2586(3) -0.20029(6) 0.0506(6) Uani 1 1 d . . . H16 H -0.0596 0.3613 -0.1985 0.061 Uiso 1 1 calc R . . C17 C 0.1791(3) 0.2545(3) -0.17595(5) 0.0408(5) Uani 1 1 d . . . H17 H 0.1943 0.3577 -0.1584 0.049 Uiso 1 1 calc R . . N18 N -0.1497(3) 0.1113(5) -0.25163(6) 0.0730(7) Uani 1 1 d . . . H8N H -0.218(5) 0.238(5) -0.2507(11) 0.102(12) Uiso 1 1 d . . . H9N H -0.132(3) 0.051(4) -0.2734(7) 0.066(7) Uiso 1 1 d . . . O9 O 0.4787(2) 0.2424(2) -0.12635(4) 0.0471(4) Uani 1 1 d . . . O10 O 0.57172(18) -0.0576(2) -0.14778(4) 0.0505(4) Uani 1 1 d . . . O1W O -0.1399(3) 0.0458(3) -0.32975(5) 0.0693(5) Uani 1 1 d . . . H1W H -0.065(5) -0.041(6) -0.3458(11) 0.125(13) Uiso 1 1 d . . . H2W H -0.095(5) 0.172(7) -0.3355(11) 0.117(13) 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 C2A 0.0253(8) 0.0310(8) 0.0302(9) 0.0005(6) 0.0008(7) -0.0028(6) C4A 0.0415(10) 0.0447(10) 0.0278(9) 0.0003(7) 0.0061(8) -0.0028(8) C5A 0.0347(10) 0.0391(10) 0.0373(10) 0.0018(7) 0.0135(8) 0.0001(7) C6A 0.0258(9) 0.0317(9) 0.0371(9) 0.0012(6) 0.0052(7) -0.0003(6) N1A 0.0213(7) 0.0350(8) 0.0305(8) 0.0010(5) 0.0013(6) -0.0005(5) N3A 0.0291(8) 0.0501(9) 0.0287(8) 0.0012(6) -0.0017(6) -0.0017(6) N7A 0.0220(8) 0.0840(14) 0.0407(11) 0.0055(8) 0.0047(7) 0.0019(7) O8A 0.0197(6) 0.0661(9) 0.0362(7) 0.0028(6) 0.0033(5) -0.0007(5) C2B 0.0239(8) 0.0353(9) 0.0324(9) -0.0007(6) 0.0009(7) 0.0005(6) C4B 0.0376(10) 0.0340(9) 0.0259(8) -0.0006(6) 0.0030(7) -0.0004(7) C5B 0.0304(9) 0.0338(9) 0.0331(9) -0.0013(6) 0.0092(7) -0.0016(6) C6B 0.0225(8) 0.0294(8) 0.0349(9) -0.0005(6) 0.0038(7) -0.0011(6) N1B 0.0224(7) 0.0420(8) 0.0245(8) -0.0002(6) 0.0020(6) -0.0009(5) N3B 0.0287(8) 0.0403(8) 0.0289(8) -0.0001(6) -0.0011(6) 0.0009(6) N7B 0.0208(8) 0.0621(11) 0.0342(10) 0.0008(7) 0.0033(7) -0.0013(6) O8B 0.0213(6) 0.0685(10) 0.0372(7) -0.0015(6) 0.0028(5) 0.0004(5) C11 0.0320(9) 0.0456(10) 0.0300(9) 0.0041(8) -0.0003(7) -0.0014(8) C12 0.0317(9) 0.0458(10) 0.0277(8) 0.0034(7) 0.0001(7) -0.0005(7) C13 0.0422(10) 0.0540(12) 0.0388(10) -0.0065(8) -0.0028(8) 0.0066(9) C14 0.0518(11) 0.0652(14) 0.0365(10) -0.0136(9) -0.0058(9) -0.0020(10) C15 0.0354(10) 0.0784(15) 0.0317(9) 0.0019(9) -0.0044(7) -0.0021(10) C16 0.0415(11) 0.0705(15) 0.0385(11) -0.0022(9) -0.0055(9) 0.0174(9) C17 0.0412(10) 0.0512(11) 0.0290(9) -0.0039(7) -0.0030(8) 0.0058(8) N18 0.0468(11) 0.122(2) 0.0464(11) -0.0089(13) -0.0176(9) 0.0073(12) O9 0.0441(8) 0.0551(9) 0.0395(8) -0.0067(6) -0.0128(6) 0.0026(6) O10 0.0408(7) 0.0574(9) 0.0509(8) -0.0015(7) -0.0117(6) 0.0119(7) O1W 0.0836(13) 0.0613(11) 0.0623(11) -0.0008(9) 0.0003(9) -0.0010(10) _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 C2A O8A 1.246(2) . ? C2A N1A 1.352(2) . ? C2A N3A 1.366(2) . ? C4A C5A 1.336(3) . ? C4A N3A 1.351(2) . ? C4A H4A 0.9300 . ? C5A C6A 1.423(3) . ? C5A H5A 0.9300 . ? C6A N7A 1.320(2) . ? C6A N1A 1.341(2) . ? N3A H1N 0.90(3) . ? N7A H2N 0.88(3) . ? N7A H3N 0.84(3) . ? C2B O8B 1.223(2) . ? C2B N3B 1.357(2) . ? C2B N1B 1.380(2) . ? C4B C5B 1.343(3) . ? C4B N3B 1.357(2) . ? C4B H4B 0.9300 . ? C5B C6B 1.416(3) . ? C5B H5B 0.9300 . ? C6B N7B 1.304(2) . ? C6B N1B 1.353(2) . ? N1B H4N 0.80(3) . ? N3B H5N 0.98(3) . ? N7B H6N 0.83(2) . ? N7B H7N 0.82(3) . ? C11 O10 1.245(2) . ? C11 O9 1.273(2) . ? C11 C12 1.493(2) . ? C12 C17 1.384(3) . ? C12 C13 1.390(3) . ? C13 C14 1.381(3) . ? C13 H13 0.9300 . ? C14 C15 1.380(3) . ? C14 H14 0.9300 . ? C15 N18 1.388(3) . ? C15 C16 1.390(3) . ? C16 C17 1.378(3) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? N18 H8N 0.96(3) . ? N18 H9N 0.91(3) . ? O1W H1W 1.01(4) . ? O1W H2W 0.91(4) . ? 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 O8A C2A N1A 121.48(15) . . ? O8A C2A N3A 119.02(15) . . ? N1A C2A N3A 119.49(15) . . ? C5A C4A N3A 120.54(16) . . ? C5A C4A H4A 119.7 . . ? N3A C4A H4A 119.7 . . ? C4A C5A C6A 117.30(16) . . ? C4A C5A H5A 121.3 . . ? C6A C5A H5A 121.3 . . ? N7A C6A N1A 117.30(17) . . ? N7A C6A C5A 121.00(17) . . ? N1A C6A C5A 121.70(16) . . ? C6A N1A C2A 119.15(15) . . ? C4A N3A C2A 121.66(15) . . ? C4A N3A H1N 121.0(15) . . ? C2A N3A H1N 116.9(15) . . ? C6A N7A H2N 120.5(17) . . ? C6A N7A H3N 115.3(17) . . ? H2N N7A H3N 124(2) . . ? O8B C2B N3B 123.56(16) . . ? O8B C2B N1B 120.71(16) . . ? N3B C2B N1B 115.73(16) . . ? C5B C4B N3B 123.00(16) . . ? C5B C4B H4B 118.5 . . ? N3B C4B H4B 118.5 . . ? C4B C5B C6B 117.44(16) . . ? C4B C5B H5B 121.3 . . ? C6B C5B H5B 121.3 . . ? N7B C6B N1B 118.58(17) . . ? N7B C6B C5B 123.62(17) . . ? N1B C6B C5B 117.80(16) . . ? C6B N1B C2B 124.49(16) . . ? C6B N1B H4N 123.5(15) . . ? C2B N1B H4N 112.0(15) . . ? C2B N3B C4B 121.53(15) . . ? C2B N3B H5N 118.5(15) . . ? C4B N3B H5N 119.8(15) . . ? C6B N7B H6N 118.7(15) . . ? C6B N7B H7N 121.8(17) . . ? H6N N7B H7N 120(2) . . ? O10 C11 O9 123.94(16) . . ? O10 C11 C12 119.73(16) . . ? O9 C11 C12 116.32(15) . . ? C17 C12 C13 117.59(16) . . ? C17 C12 C11 120.29(16) . . ? C13 C12 C11 122.08(16) . . ? C14 C13 C12 121.09(18) . . ? C14 C13 H13 119.5 . . ? C12 C13 H13 119.5 . . ? C15 C14 C13 120.90(19) . . ? C15 C14 H14 119.6 . . ? C13 C14 H14 119.6 . . ? C14 C15 N18 120.9(2) . . ? C14 C15 C16 118.36(18) . . ? N18 C15 C16 120.7(2) . . ? C17 C16 C15 120.45(18) . . ? C17 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? C16 C17 C12 121.58(17) . . ? C16 C17 H17 119.2 . . ? C12 C17 H17 119.2 . . ? C15 N18 H8N 113(2) . . ? C15 N18 H9N 113.5(16) . . ? H8N N18 H9N 120(3) . . ? H1W O1W H2W 98(3) . . ? 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 N3A C4A C5A C6A 2.0(3) . . . . ? C4A C5A C6A N7A 176.26(17) . . . . ? C4A C5A C6A N1A -3.7(2) . . . . ? N7A C6A N1A C2A -178.32(15) . . . . ? C5A C6A N1A C2A 1.6(2) . . . . ? O8A C2A N1A C6A -179.20(15) . . . . ? N3A C2A N1A C6A 2.0(2) . . . . ? C5A C4A N3A C2A 1.6(3) . . . . ? O8A C2A N3A C4A 177.48(16) . . . . ? N1A C2A N3A C4A -3.7(2) . . . . ? N3B C4B C5B C6B 0.4(2) . . . . ? C4B C5B C6B N7B 179.11(15) . . . . ? C4B C5B C6B N1B -1.0(2) . . . . ? N7B C6B N1B C2B -179.05(15) . . . . ? C5B C6B N1B C2B 1.0(2) . . . . ? O8B C2B N1B C6B 179.60(15) . . . . ? N3B C2B N1B C6B -0.4(2) . . . . ? O8B C2B N3B C4B 179.73(15) . . . . ? N1B C2B N3B C4B -0.3(2) . . . . ? C5B C4B N3B C2B 0.3(2) . . . . ? O10 C11 C12 C17 173.04(17) . . . . ? O9 C11 C12 C17 -5.9(2) . . . . ? O10 C11 C12 C13 -4.5(3) . . . . ? O9 C11 C12 C13 176.58(17) . . . . ? C17 C12 C13 C14 -0.7(3) . . . . ? C11 C12 C13 C14 176.95(18) . . . . ? C12 C13 C14 C15 -0.1(3) . . . . ? C13 C14 C15 N18 -177.7(2) . . . . ? C13 C14 C15 C16 -0.1(3) . . . . ? C14 C15 C16 C17 1.2(3) . . . . ? N18 C15 C16 C17 178.8(2) . . . . ? C15 C16 C17 C12 -2.0(3) . . . . ? C13 C12 C17 C16 1.7(3) . . . . ? C11 C12 C17 C16 -175.92(18) . . . . ? 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 N3A H1N O10 0.90(3) 1.94(3) 2.830(2) 168(2) 3_755 N7A H2N O8A 0.88(3) 2.09(3) 2.847(2) 144(2) 1_455 N7A H3N O8B 0.84(3) 2.12(3) 2.956(2) 176(2) . N1B H4N N1A 0.80(3) 2.07(3) 2.866(2) 174(2) . N3B H5N O9 0.98(3) 1.64(3) 2.601(2) 167(2) . N7B H6N O8A 0.83(2) 1.94(3) 2.762(2) 176(2) . N7B H7N O8B 0.82(3) 2.07(3) 2.845(2) 158(2) 1_655 N18 H8N N18 0.96(3) 2.61(3) 3.559(4) 170(3) 2_454 N18 H9N O1W 0.91(3) 2.08(3) 2.925(3) 154(2) . O1W H1W O9 1.01(4) 1.88(4) 2.862(3) 164(3) 2_544 O1W H2W O10 0.91(4) 1.87(5) 2.752(3) 164(4) 2_554 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.325 _refine_diff_density_min -0.307 _refine_diff_density_rms 0.076