# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_publication_text _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _publ_contact_author_name 'Srinivasulu Aitipamula' _publ_contact_author_address ; 'Institute of Chemical and Engineering Sciences, A*STAR (Agency for Science, Technology and Research), 1, Pesek Road, Jurong Island, Singapore, 627833.' ; _publ_contact_author_email 'srinivasulu aitipamula@ices.a-star.edu.sg' _publ_contact_author_phone '(65) 6796 3858' _publ_contact_author_fax '(65) 6316 6183' loop_ _publ_author_name _publ_author_address S.Aitipamula ; 'Institute of Chemical and Engineering Sciences, A*STAR (Agency for Science, Technology and Research), 1, Pesek Road, Jurong Island, Singapore, 627833.' ; P.S.Chow ; 'Institute of Chemical and Engineering Sciences, A*STAR (Agency for Science, Technology and Research), 1, Pesek Road, Jurong Island, Singapore, 627833.' ; R.B.H.Tan ; 'Institute of Chemical and Engineering Sciences, A*STAR (Agency for Science, Technology and Research), 1, Pesek Road, Jurong Island, Singapore, 627833. Department of Chemical & Biomolecular Engineering, National University of Singapore, 4 Engineering Drive 4, Singapore 117576.' ; data_CAF-HBA _database_code_depnum_ccdc_archive 'CCDC 863197' #TrackingRef '- CAF-PA-4HBA Combined CIF.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 'MOnohydrate of caffeine-4HBA (1:1)' ; _chemical_name_common 'MOnohydrate of caffeine-4HBA (1:1)' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H18 N4 O6' _chemical_formula_weight 350.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.2188(14) _cell_length_b 8.5282(17) _cell_length_c 13.827(3) _cell_angle_alpha 90.33(3) _cell_angle_beta 101.29(3) _cell_angle_gamma 107.57(3) _cell_volume 793.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 1907 _cell_measurement_theta_min 2.5112 _cell_measurement_theta_max 30.8977 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.466 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 368 _exptl_absorpt_coefficient_mu 0.115 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9511 _exptl_absorpt_correction_T_max 0.9863 _exptl_absorpt_process_details 'R. H. Blessing, Acta Cryst. 1995 A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(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 'Rigaku Saturn 70 CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12024 _diffrn_reflns_av_R_equivalents 0.0274 _diffrn_reflns_av_sigmaI/netI 0.0295 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.51 _diffrn_reflns_theta_max 28.28 _reflns_number_total 3907 _reflns_number_gt 3511 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0543P)^2^+0.4144P] 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 3907 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0658 _refine_ls_R_factor_gt 0.0581 _refine_ls_wR_factor_ref 0.1365 _refine_ls_wR_factor_gt 0.1300 _refine_ls_goodness_of_fit_ref 1.139 _refine_ls_restrained_S_all 1.139 _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 O5 O 0.9909(2) 0.00282(16) 0.81752(9) 0.0270(3) Uani 1 1 d . . . O2 O 0.44690(19) 0.99146(14) 0.12798(9) 0.0244(3) Uani 1 1 d . . . O1 O 0.2413(2) 0.43733(15) 0.04207(10) 0.0309(3) Uani 1 1 d . . . N1 N 0.3451(2) 0.71294(17) 0.08593(10) 0.0209(3) Uani 1 1 d . . . O3 O 0.8426(2) 0.61537(16) 0.58764(10) 0.0314(3) Uani 1 1 d . . . O4 O 0.6914(2) 0.40403(17) 0.47359(9) 0.0303(3) Uani 1 1 d . . . N4 N 0.6274(2) 0.64415(18) 0.35762(10) 0.0232(3) Uani 1 1 d . . . N2 N 0.4210(2) 0.52101(17) 0.19792(10) 0.0219(3) Uani 1 1 d . . . C3 C 0.5487(2) 0.8113(2) 0.24138(12) 0.0196(3) Uani 1 1 d . . . C2 C 0.5294(2) 0.6524(2) 0.26434(12) 0.0200(3) Uani 1 1 d . . . N3 N 0.6678(2) 0.90809(17) 0.32463(10) 0.0218(3) Uani 1 1 d . . . C10 C 0.7718(3) 0.1758(2) 0.60265(12) 0.0227(3) Uani 1 1 d . . . H10 H 0.6880 0.1378 0.5396 0.027 Uiso 1 1 calc R . . C9 C 0.8427(2) 0.3442(2) 0.63001(12) 0.0217(3) Uani 1 1 d . . . C4 C 0.4491(2) 0.8521(2) 0.15045(12) 0.0197(3) Uani 1 1 d . . . C1 C 0.3319(3) 0.5503(2) 0.10537(12) 0.0225(3) Uani 1 1 d . . . C13 C 1.0146(3) 0.2863(2) 0.78764(12) 0.0229(3) Uani 1 1 d . . . H13 H 1.0968 0.3244 0.8510 0.027 Uiso 1 1 calc R . . C14 C 0.9637(3) 0.3974(2) 0.72329(12) 0.0236(4) Uani 1 1 d . . . H12 H 1.0120 0.5118 0.7430 0.028 Uiso 1 1 calc R . . C15 C 0.7942(3) 0.4687(2) 0.56342(12) 0.0236(4) Uani 1 1 d . . . C11 C 0.8218(3) 0.0631(2) 0.66619(12) 0.0242(4) Uani 1 1 d . . . H11 H 0.7724 -0.0514 0.6466 0.029 Uiso 1 1 calc R . . C6 C 0.2419(3) 0.7413(2) -0.01173(13) 0.0288(4) Uani 1 1 d . . . H6A H 0.1960 0.6391 -0.0543 0.043 Uiso 1 1 calc R . . H6B H 0.3332 0.8275 -0.0415 0.043 Uiso 1 1 calc R . . H6C H 0.1276 0.7764 -0.0046 0.043 Uiso 1 1 calc R . . C12 C 0.9447(3) 0.1180(2) 0.75894(12) 0.0227(3) Uani 1 1 d . . . C7 C 0.4011(3) 0.3509(2) 0.22285(14) 0.0324(4) Uani 1 1 d . . . H7A H 0.2658 0.2803 0.1948 0.049 Uiso 1 1 calc R . . H7B H 0.4279 0.3463 0.2949 0.049 Uiso 1 1 calc R . . H7C H 0.4962 0.3121 0.1956 0.049 Uiso 1 1 calc R . . C8 C 0.7434(3) 1.0878(2) 0.33545(13) 0.0274(4) Uani 1 1 d . . . H8A H 0.8452 1.1228 0.3963 0.041 Uiso 1 1 calc R . . H8B H 0.6342 1.1321 0.3387 0.041 Uiso 1 1 calc R . . H8C H 0.8014 1.1290 0.2786 0.041 Uiso 1 1 calc R . . C5 C 0.7097(3) 0.8023(2) 0.39069(12) 0.0237(3) Uani 1 1 d . . . H5 H 0.7901 0.8368 0.4548 0.028 Uiso 1 1 calc R . . O6 O 0.2427(2) 0.13533(17) -0.01838(10) 0.0302(3) Uani 1 1 d . . . H1 H 0.663(4) 0.495(4) 0.432(2) 0.066(9) Uiso 1 1 d . . . H3 H 0.248(4) 0.235(4) 0.013(2) 0.055(8) Uiso 1 1 d . . . H4 H 0.292(4) 0.082(3) 0.030(2) 0.051(7) Uiso 1 1 d . . . H2 H 1.082(4) 0.054(4) 0.877(2) 0.064(9) 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 O5 0.0319(7) 0.0261(6) 0.0221(6) 0.0059(5) 0.0009(5) 0.0107(5) O2 0.0290(7) 0.0205(6) 0.0238(6) 0.0045(5) 0.0038(5) 0.0090(5) O1 0.0383(8) 0.0215(6) 0.0269(6) -0.0030(5) -0.0045(6) 0.0076(6) N1 0.0248(7) 0.0176(7) 0.0179(6) 0.0023(5) 0.0009(5) 0.0054(6) O3 0.0352(7) 0.0246(6) 0.0302(7) 0.0032(5) -0.0006(6) 0.0076(6) O4 0.0414(8) 0.0298(7) 0.0201(6) 0.0037(5) -0.0006(5) 0.0162(6) N4 0.0235(7) 0.0277(7) 0.0191(7) 0.0046(5) 0.0030(6) 0.0098(6) N2 0.0254(7) 0.0185(7) 0.0201(7) 0.0016(5) 0.0020(6) 0.0063(6) C3 0.0200(8) 0.0208(8) 0.0186(7) 0.0012(6) 0.0045(6) 0.0065(6) C2 0.0188(8) 0.0212(8) 0.0204(7) 0.0019(6) 0.0047(6) 0.0062(6) N3 0.0225(7) 0.0217(7) 0.0203(7) 0.0005(5) 0.0032(5) 0.0063(6) C10 0.0217(8) 0.0279(9) 0.0179(7) 0.0020(6) 0.0034(6) 0.0074(7) C9 0.0212(8) 0.0245(8) 0.0202(8) 0.0037(6) 0.0043(6) 0.0083(7) C4 0.0199(8) 0.0186(7) 0.0206(7) 0.0023(6) 0.0048(6) 0.0057(6) C1 0.0230(8) 0.0208(8) 0.0226(8) 0.0022(6) 0.0023(6) 0.0067(7) C13 0.0216(8) 0.0264(8) 0.0195(7) 0.0025(6) 0.0025(6) 0.0069(7) C14 0.0229(8) 0.0259(8) 0.0224(8) 0.0040(6) 0.0051(7) 0.0080(7) C15 0.0223(8) 0.0272(8) 0.0218(8) 0.0044(7) 0.0050(6) 0.0082(7) C11 0.0258(9) 0.0249(8) 0.0216(8) 0.0036(6) 0.0048(7) 0.0076(7) C6 0.0334(10) 0.0259(9) 0.0199(8) 0.0037(7) -0.0050(7) 0.0050(8) C12 0.0222(8) 0.0258(8) 0.0214(8) 0.0049(6) 0.0050(6) 0.0088(7) C7 0.0432(11) 0.0197(8) 0.0306(9) 0.0044(7) -0.0003(8) 0.0093(8) C8 0.0312(10) 0.0223(8) 0.0245(8) -0.0020(7) 0.0022(7) 0.0046(7) C5 0.0238(8) 0.0279(8) 0.0194(7) 0.0019(6) 0.0034(6) 0.0090(7) O6 0.0386(8) 0.0305(7) 0.0217(6) -0.0001(5) -0.0036(5) 0.0173(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 O5 C12 1.354(2) . ? O5 H2 0.95(3) . ? O2 C4 1.234(2) . ? O1 C1 1.228(2) . ? N1 C1 1.393(2) . ? N1 C4 1.398(2) . ? N1 C6 1.468(2) . ? O3 C15 1.218(2) . ? O4 C15 1.335(2) . ? O4 H1 1.01(3) . ? N4 C5 1.336(2) . ? N4 C2 1.357(2) . ? N2 C2 1.374(2) . ? N2 C1 1.375(2) . ? N2 C7 1.464(2) . ? C3 C2 1.366(2) . ? C3 N3 1.385(2) . ? C3 C4 1.422(2) . ? N3 C5 1.343(2) . ? N3 C8 1.459(2) . ? C10 C11 1.386(2) . ? C10 C9 1.393(2) . ? C10 H10 0.9500 . ? C9 C14 1.395(2) . ? C9 C15 1.486(2) . ? C13 C14 1.384(2) . ? C13 C12 1.397(2) . ? C13 H13 0.9500 . ? C14 H12 0.9500 . ? C11 C12 1.396(2) . ? C11 H11 0.9500 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C5 H5 0.9500 . ? O6 H3 0.94(3) . ? O6 H4 0.89(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 C12 O5 H2 110.6(18) . . ? C1 N1 C4 126.09(14) . . ? C1 N1 C6 117.06(14) . . ? C4 N1 C6 116.85(14) . . ? C15 O4 H1 109.0(16) . . ? C5 N4 C2 103.27(15) . . ? C2 N2 C1 119.19(14) . . ? C2 N2 C7 121.50(14) . . ? C1 N2 C7 119.31(14) . . ? C2 C3 N3 105.34(14) . . ? C2 C3 C4 122.75(15) . . ? N3 C3 C4 131.80(15) . . ? N4 C2 C3 111.98(15) . . ? N4 C2 N2 126.30(15) . . ? C3 C2 N2 121.72(15) . . ? C5 N3 C3 105.77(14) . . ? C5 N3 C8 127.22(15) . . ? C3 N3 C8 126.88(14) . . ? C11 C10 C9 120.88(16) . . ? C11 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? C10 C9 C14 118.66(16) . . ? C10 C9 C15 122.38(15) . . ? C14 C9 C15 118.96(16) . . ? O2 C4 N1 121.53(15) . . ? O2 C4 C3 126.23(16) . . ? N1 C4 C3 112.23(14) . . ? O1 C1 N2 121.50(16) . . ? O1 C1 N1 120.74(15) . . ? N2 C1 N1 117.75(15) . . ? C14 C13 C12 119.70(16) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? C13 C14 C9 121.14(17) . . ? C13 C14 H12 119.4 . . ? C9 C14 H12 119.4 . . ? O3 C15 O4 122.90(16) . . ? O3 C15 C9 123.85(16) . . ? O4 C15 C9 113.25(15) . . ? C10 C11 C12 119.92(17) . . ? C10 C11 H11 120.0 . . ? C12 C11 H11 120.0 . . ? N1 C6 H6A 109.5 . . ? N1 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N1 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? O5 C12 C11 117.47(16) . . ? O5 C12 C13 122.84(16) . . ? C11 C12 C13 119.69(16) . . ? N2 C7 H7A 109.5 . . ? N2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N3 C8 H8A 109.5 . . ? N3 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N3 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N4 C5 N3 113.63(15) . . ? N4 C5 H5 123.2 . . ? N3 C5 H5 123.2 . . ? H3 O6 H4 104(2) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.246 _refine_diff_density_min -0.235 _refine_diff_density_rms 0.054 #====END data_PA-HBA _database_code_depnum_ccdc_archive 'CCDC 863198' #TrackingRef '- CAF-PA-4HBA Combined CIF.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 'Monohydrate of Piracetam-4-hydroxybenzoic acid (1:1)' ; _chemical_name_common 'Monohydrate of Piracetam-4-hydroxybenzoic acid (1:1)' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H18 N2 O6' _chemical_formula_weight 298.29 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.4211(13) _cell_length_b 6.6058(13) _cell_length_c 16.590(3) _cell_angle_alpha 96.20(3) _cell_angle_beta 96.76(3) _cell_angle_gamma 90.86(3) _cell_volume 694.4(2) _cell_formula_units_Z 2 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 1708 _cell_measurement_theta_min 2.4879 _cell_measurement_theta_max 30.8212 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.427 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 316 _exptl_absorpt_coefficient_mu 0.114 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9634 _exptl_absorpt_correction_T_max 0.9754 _exptl_absorpt_process_details 'R. H. Blessing, Acta Cryst. 1995 A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(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 'Rigaku Saturn 70 CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9683 _diffrn_reflns_av_R_equivalents 0.0178 _diffrn_reflns_av_sigmaI/netI 0.0173 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.49 _diffrn_reflns_theta_max 28.28 _reflns_number_total 3396 _reflns_number_gt 3233 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0564P)^2^+0.2430P] 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 3396 _refine_ls_number_parameters 214 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0445 _refine_ls_R_factor_gt 0.0425 _refine_ls_wR_factor_ref 0.1119 _refine_ls_wR_factor_gt 0.1102 _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_restrained_S_all 1.088 _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 O3 O 0.22562(14) 0.15298(13) 0.48097(5) 0.02275(19) Uani 1 1 d . . . O4 O -0.12017(14) 0.15531(13) 0.44113(5) 0.02240(19) Uani 1 1 d . . . O5 O 0.19129(15) 0.94409(13) 0.29817(5) 0.0242(2) Uani 1 1 d . . . C7 C 0.09977(18) 0.41509(16) 0.40407(6) 0.0186(2) Uani 1 1 d . . . C8 C 0.30381(19) 0.49111(17) 0.40362(7) 0.0208(2) Uani 1 1 d . . . H8 H 0.4195 0.4212 0.4275 0.025 Uiso 1 1 calc R . . C9 C 0.33841(19) 0.66820(18) 0.36848(7) 0.0214(2) Uani 1 1 d . . . H9 H 0.4774 0.7193 0.3682 0.026 Uiso 1 1 calc R . . C11 C -0.03631(19) 0.69583(17) 0.33387(7) 0.0202(2) Uani 1 1 d . . . H11 H -0.1523 0.7655 0.3101 0.024 Uiso 1 1 calc R . . C12 C -0.06905(19) 0.51887(17) 0.36909(7) 0.0201(2) Uani 1 1 d . . . H12 H -0.2080 0.4678 0.3694 0.024 Uiso 1 1 calc R . . C10 C 0.16774(19) 0.77124(17) 0.33340(7) 0.0197(2) Uani 1 1 d . . . C13 C 0.05829(18) 0.23065(17) 0.44286(6) 0.0191(2) Uani 1 1 d . . . O1 O 0.61006(13) 0.34714(13) 0.19323(5) 0.0240(2) Uani 1 1 d . . . O2 O 0.20486(14) 0.18769(13) 0.04090(5) 0.0237(2) Uani 1 1 d . . . N1 N 0.31399(15) 0.51789(14) 0.15316(6) 0.0181(2) Uani 1 1 d . . . N2 N -0.09593(16) 0.12897(16) 0.09494(6) 0.0226(2) Uani 1 1 d . . . C5 C 0.16286(18) 0.37028(17) 0.17105(7) 0.0191(2) Uani 1 1 d . . . H5A H 0.0401 0.4416 0.1900 0.023 Uiso 1 1 calc R . . H5B H 0.2265 0.2939 0.2155 0.023 Uiso 1 1 calc R . . C6 C 0.09073(18) 0.22094(16) 0.09517(7) 0.0184(2) Uani 1 1 d . . . C1 C 0.52058(18) 0.48743(17) 0.16019(6) 0.0190(2) Uani 1 1 d . . . C4 C 0.24875(19) 0.68452(18) 0.10524(7) 0.0224(2) Uani 1 1 d . . . H4A H 0.1519 0.7748 0.1334 0.027 Uiso 1 1 calc R . . H4B H 0.1787 0.6314 0.0505 0.027 Uiso 1 1 calc R . . C3 C 0.4551(2) 0.7978(2) 0.09878(9) 0.0286(3) Uani 1 1 d . . . H3A H 0.4596 0.8342 0.0426 0.034 Uiso 1 1 calc R . . H3B H 0.4715 0.9239 0.1373 0.034 Uiso 1 1 calc R . . C2 C 0.62707(19) 0.64946(19) 0.12065(8) 0.0256(3) Uani 1 1 d . . . H2A H 0.6852 0.5893 0.0711 0.031 Uiso 1 1 calc R . . H2B H 0.7423 0.7192 0.1590 0.031 Uiso 1 1 calc R . . O6 O 0.58525(15) 0.06848(14) 0.30107(6) 0.0277(2) Uani 1 1 d . . . H6 H -0.141(3) 0.037(3) 0.0534(11) 0.029(4) Uiso 1 1 d . . . H1 H -0.176(3) 0.169(3) 0.1311(12) 0.038(5) Uiso 1 1 d . . . H13 H 0.586(3) 0.169(3) 0.2692(12) 0.042(5) Uiso 1 1 d . . . H7 H 0.179(3) 0.041(3) 0.5056(13) 0.056(6) Uiso 1 1 d . . . H14 H 0.670(4) 0.107(3) 0.3461(15) 0.060(6) Uiso 1 1 d . . . H10 H 0.334(4) 0.976(3) 0.3032(13) 0.052(6) 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 O3 0.0243(4) 0.0218(4) 0.0228(4) 0.0076(3) 0.0011(3) -0.0011(3) O4 0.0238(4) 0.0213(4) 0.0225(4) 0.0056(3) 0.0020(3) -0.0034(3) O5 0.0268(5) 0.0200(4) 0.0270(4) 0.0087(3) 0.0032(3) -0.0012(3) C7 0.0229(6) 0.0165(5) 0.0166(5) 0.0014(4) 0.0042(4) -0.0001(4) C8 0.0221(6) 0.0198(5) 0.0208(5) 0.0037(4) 0.0030(4) 0.0010(4) C9 0.0212(5) 0.0209(5) 0.0230(5) 0.0046(4) 0.0040(4) -0.0012(4) C11 0.0228(5) 0.0183(5) 0.0195(5) 0.0022(4) 0.0022(4) 0.0021(4) C12 0.0216(5) 0.0188(5) 0.0201(5) 0.0013(4) 0.0043(4) -0.0008(4) C10 0.0263(6) 0.0156(5) 0.0175(5) 0.0022(4) 0.0041(4) -0.0008(4) C13 0.0240(6) 0.0175(5) 0.0157(5) 0.0008(4) 0.0031(4) -0.0002(4) O1 0.0215(4) 0.0275(4) 0.0252(4) 0.0106(3) 0.0049(3) 0.0051(3) O2 0.0243(4) 0.0244(4) 0.0226(4) -0.0015(3) 0.0084(3) -0.0024(3) N1 0.0175(4) 0.0178(4) 0.0192(4) 0.0026(3) 0.0025(3) 0.0004(3) N2 0.0212(5) 0.0232(5) 0.0232(5) -0.0016(4) 0.0059(4) -0.0028(4) C5 0.0186(5) 0.0209(5) 0.0182(5) 0.0016(4) 0.0042(4) -0.0011(4) C6 0.0198(5) 0.0164(5) 0.0194(5) 0.0031(4) 0.0028(4) 0.0021(4) C1 0.0196(5) 0.0215(5) 0.0162(5) 0.0023(4) 0.0035(4) 0.0013(4) C4 0.0217(5) 0.0196(5) 0.0265(6) 0.0065(4) 0.0005(4) 0.0023(4) C3 0.0262(6) 0.0228(6) 0.0385(7) 0.0102(5) 0.0046(5) 0.0008(5) C2 0.0210(6) 0.0288(6) 0.0287(6) 0.0111(5) 0.0035(4) -0.0013(5) O6 0.0286(5) 0.0263(5) 0.0286(5) 0.0114(4) -0.0018(4) -0.0051(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 O3 C13 1.3207(15) . ? O3 H7 0.94(2) . ? O4 C13 1.2384(15) . ? O5 C10 1.3520(14) . ? O5 H10 0.93(2) . ? C7 C12 1.3936(17) . ? C7 C8 1.3972(16) . ? C7 C13 1.4728(16) . ? C8 C9 1.3884(16) . ? C8 H8 0.9500 . ? C9 C10 1.4003(17) . ? C9 H9 0.9500 . ? C11 C12 1.3860(16) . ? C11 C10 1.3959(17) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? O1 C1 1.2413(15) . ? O2 C6 1.2302(14) . ? N1 C1 1.3381(15) . ? N1 C5 1.4430(15) . ? N1 C4 1.4641(15) . ? N2 C6 1.3350(15) . ? N2 H6 0.887(17) . ? N2 H1 0.860(19) . ? C5 C6 1.5341(16) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C1 C2 1.5094(17) . ? C4 C3 1.5324(17) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C3 C2 1.5252(18) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? O6 H13 0.90(2) . ? O6 H14 0.88(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 C13 O3 H7 107.5(14) . . ? C10 O5 H10 107.6(13) . . ? C12 C7 C8 119.42(11) . . ? C12 C7 C13 119.06(11) . . ? C8 C7 C13 121.49(11) . . ? C9 C8 C7 120.37(11) . . ? C9 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? C8 C9 C10 119.78(11) . . ? C8 C9 H9 120.1 . . ? C10 C9 H9 120.1 . . ? C12 C11 C10 119.76(11) . . ? C12 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? C11 C12 C7 120.69(11) . . ? C11 C12 H12 119.7 . . ? C7 C12 H12 119.7 . . ? O5 C10 C11 117.47(11) . . ? O5 C10 C9 122.55(11) . . ? C11 C10 C9 119.99(11) . . ? O4 C13 O3 122.28(11) . . ? O4 C13 C7 122.76(11) . . ? O3 C13 C7 114.95(10) . . ? C1 N1 C5 123.09(10) . . ? C1 N1 C4 113.92(10) . . ? C5 N1 C4 120.99(10) . . ? C6 N2 H6 118.4(11) . . ? C6 N2 H1 120.4(12) . . ? H6 N2 H1 120.7(16) . . ? N1 C5 C6 110.85(9) . . ? N1 C5 H5A 109.5 . . ? C6 C5 H5A 109.5 . . ? N1 C5 H5B 109.5 . . ? C6 C5 H5B 109.5 . . ? H5A C5 H5B 108.1 . . ? O2 C6 N2 124.26(11) . . ? O2 C6 C5 120.36(10) . . ? N2 C6 C5 115.34(10) . . ? O1 C1 N1 125.43(11) . . ? O1 C1 C2 125.46(11) . . ? N1 C1 C2 109.11(10) . . ? N1 C4 C3 103.73(10) . . ? N1 C4 H4A 111.0 . . ? C3 C4 H4A 111.0 . . ? N1 C4 H4B 111.0 . . ? C3 C4 H4B 111.0 . . ? H4A C4 H4B 109.0 . . ? C2 C3 C4 105.24(10) . . ? C2 C3 H3A 110.7 . . ? C4 C3 H3A 110.7 . . ? C2 C3 H3B 110.7 . . ? C4 C3 H3B 110.7 . . ? H3A C3 H3B 108.8 . . ? C1 C2 C3 104.98(10) . . ? C1 C2 H2A 110.8 . . ? C3 C2 H2A 110.8 . . ? C1 C2 H2B 110.8 . . ? C3 C2 H2B 110.8 . . ? H2A C2 H2B 108.8 . . ? H13 O6 H14 107.4(19) . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.332 _refine_diff_density_min -0.215 _refine_diff_density_rms 0.046 #====END