# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'M. Zaworotko' _publ_contact_author_address ; Chair, Department of Chemistry University of South Florida 4202 East Fowler Avenue Tampa Florida 33620-5250 USA ; _publ_contact_author_email XTAL@USF.EDU _publ_section_title ; Crystal engineering of pharmaceutical co-crystals of Piracetam from polymorphic active pharmaceutical ingredients ; loop_ _publ_author_name 'Peddy Vishweshwar' 'Jennifer A. McMahon' 'Matthew L. Peterson' 'Magali B. Hickey' 'Tanise R. Shattock' 'Michael J. Zaworotko' data_jam253a _database_code_depnum_ccdc_archive 'CCDC 262605' _audit_creation_method SHELXL-97 _exptl_crystal_preparation Acetonitrile _chemical_name_systematic ; 1:1 co-crystal of 2-oxo-1-pyrrolidinyl)acetamide and 2,5-dihydroxybenzoic acid' ; _chemical_name_common ;1:1 co-crystal of 2-oxo-1-pyrrolidinyl)acetamide and 2,5- dihydroxybenzoic acid' ; _chemical_melting_point '399 K' _chemical_formula_moiety 'C6 H10 N2 O2, C7 H6 O4' _chemical_formula_sum 'C13 H16 N2 O6' _chemical_formula_weight 296.28 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 'C 2/c' _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' '-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 27.896(3) _cell_length_b 5.1762(5) _cell_length_c 19.7879(18) _cell_angle_alpha 90.00 _cell_angle_beta 101.090(2) _cell_angle_gamma 90.00 _cell_volume 2803.9(4) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4559 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 27.97 _exptl_crystal_description parallelpipe _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.404 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1248 _exptl_absorpt_coefficient_mu 0.112 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min 0.636 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7622 _diffrn_reflns_av_R_equivalents 0.0253 _diffrn_reflns_av_sigmaI/netI 0.0320 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.49 _diffrn_reflns_theta_max 26.37 _reflns_number_total 2873 _reflns_number_gt 2417 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0508P)^2^+1.6871P] 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 2873 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0519 _refine_ls_R_factor_gt 0.0435 _refine_ls_wR_factor_ref 0.1131 _refine_ls_wR_factor_gt 0.1083 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 O1 O 0.34363(5) 0.2255(2) 0.43070(6) 0.0370(3) Uani 1 1 d . . . O2 O 0.35809(4) 0.2411(2) 0.26517(6) 0.0309(3) Uani 1 1 d . . . N1 N 0.33301(5) 0.5764(2) 0.35993(6) 0.0252(3) Uani 1 1 d . . . N2 N 0.43824(5) 0.3504(3) 0.29017(8) 0.0379(4) Uani 1 1 d . . . H2AN H 0.4409 0.2402 0.2555 0.045 Uiso 1 1 d R . . H2BN H 0.4599 0.4552 0.3146 0.045 Uiso 1 1 d R . . C1 C 0.31699(6) 0.3941(3) 0.39881(8) 0.0264(3) Uani 1 1 d . . . C2 C 0.26274(6) 0.4296(3) 0.39372(10) 0.0356(4) Uani 1 1 d . . . H2A H 0.2541 0.4285 0.4400 0.043 Uiso 1 1 calc R . . H2B H 0.2442 0.2913 0.3655 0.043 Uiso 1 1 calc R . . C3 C 0.25203(6) 0.6934(3) 0.35912(10) 0.0371(4) Uani 1 1 d . . . H3A H 0.2525 0.8316 0.3938 0.045 Uiso 1 1 calc R . . H3B H 0.2199 0.6937 0.3276 0.045 Uiso 1 1 calc R . . C4 C 0.29367(6) 0.7295(3) 0.31919(9) 0.0314(4) Uani 1 1 d . . . H4A H 0.2845 0.6625 0.2716 0.038 Uiso 1 1 calc R . . H4B H 0.3031 0.9136 0.3176 0.038 Uiso 1 1 calc R . . C5 C 0.38289(6) 0.5771(3) 0.34933(8) 0.0284(4) Uani 1 1 d . . . H5A H 0.4051 0.5449 0.3939 0.034 Uiso 1 1 calc R . . H5B H 0.3906 0.7499 0.3329 0.034 Uiso 1 1 calc R . . C6 C 0.39205(6) 0.3737(3) 0.29737(8) 0.0259(3) Uani 1 1 d . . . O11 O 0.49451(4) 0.6867(2) 0.11585(6) 0.0333(3) Uani 1 1 d . . . H11O H 0.4892 0.8149 0.1428 0.040 Uiso 1 1 d R . . O12 O 0.32487(4) 0.1305(2) 0.02008(6) 0.0365(3) Uani 1 1 d . . . H12O H 0.3300 0.0041 -0.0079 0.044 Uiso 1 1 d R . . O13 O 0.36464(4) 0.8578(2) 0.18330(6) 0.0310(3) Uani 1 1 d . . . H13O H 0.3666 0.9959 0.2117 0.037 Uiso 1 1 d R . . O14 O 0.44400(4) 0.9500(2) 0.18900(6) 0.0320(3) Uani 1 1 d . . . C11 C 0.40807(6) 0.6092(3) 0.11495(8) 0.0243(3) Uani 1 1 d . . . C12 C 0.45212(6) 0.5502(3) 0.09307(8) 0.0257(3) Uani 1 1 d . . . C13 C 0.45324(6) 0.3457(3) 0.04762(8) 0.0290(4) Uani 1 1 d . . . H13 H 0.4829 0.3039 0.0332 0.035 Uiso 1 1 calc R . . C14 C 0.41132(6) 0.2025(3) 0.02326(8) 0.0278(4) Uani 1 1 d . . . H14 H 0.4126 0.0627 -0.0075 0.033 Uiso 1 1 calc R . . C15 C 0.36710(6) 0.2623(3) 0.04362(8) 0.0270(3) Uani 1 1 d . . . C16 C 0.36608(6) 0.4643(3) 0.08945(8) 0.0271(3) Uani 1 1 d . . . H16 H 0.3364 0.5050 0.1038 0.032 Uiso 1 1 calc R . . C17 C 0.40712(6) 0.8202(3) 0.16518(8) 0.0253(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0430(7) 0.0322(6) 0.0353(7) 0.0085(5) 0.0067(6) 0.0069(6) O2 0.0278(6) 0.0328(6) 0.0326(6) -0.0094(5) 0.0070(5) -0.0045(5) N1 0.0277(7) 0.0237(6) 0.0245(7) -0.0011(5) 0.0055(5) -0.0004(6) N2 0.0288(8) 0.0428(8) 0.0426(9) -0.0189(7) 0.0082(6) -0.0059(7) C1 0.0332(9) 0.0232(8) 0.0236(8) -0.0030(6) 0.0072(6) -0.0004(7) C2 0.0331(9) 0.0294(8) 0.0470(10) 0.0009(8) 0.0146(8) -0.0009(8) C3 0.0280(9) 0.0315(9) 0.0509(11) -0.0007(8) 0.0052(8) 0.0011(7) C4 0.0355(9) 0.0244(8) 0.0322(9) 0.0040(7) 0.0013(7) 0.0012(7) C5 0.0271(8) 0.0301(8) 0.0284(8) -0.0048(7) 0.0065(6) -0.0038(7) C6 0.0277(8) 0.0268(8) 0.0235(8) 0.0015(6) 0.0058(6) -0.0021(7) O11 0.0240(6) 0.0325(6) 0.0431(7) -0.0057(5) 0.0059(5) 0.0013(5) O12 0.0324(6) 0.0399(7) 0.0380(7) -0.0131(6) 0.0089(5) -0.0076(5) O13 0.0296(6) 0.0309(6) 0.0338(6) -0.0089(5) 0.0096(5) -0.0013(5) O14 0.0282(6) 0.0327(6) 0.0345(6) -0.0062(5) 0.0045(5) -0.0006(5) C11 0.0270(8) 0.0237(7) 0.0217(7) 0.0038(6) 0.0037(6) 0.0029(6) C12 0.0249(8) 0.0245(7) 0.0268(8) 0.0051(6) 0.0028(6) 0.0023(7) C13 0.0282(8) 0.0301(8) 0.0301(9) 0.0030(7) 0.0094(7) 0.0055(7) C14 0.0367(9) 0.0245(8) 0.0229(8) -0.0008(6) 0.0076(7) 0.0030(7) C15 0.0305(8) 0.0281(8) 0.0218(8) 0.0010(6) 0.0038(6) -0.0008(7) C16 0.0261(8) 0.0302(8) 0.0260(8) 0.0013(7) 0.0075(6) 0.0018(7) C17 0.0274(8) 0.0260(7) 0.0220(8) 0.0034(6) 0.0034(6) 0.0014(7) _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 O1 C1 1.2377(19) . ? O2 C6 1.2419(19) . ? N1 C1 1.347(2) . ? N1 C5 1.4465(19) . ? N1 C4 1.464(2) . ? N2 C6 1.329(2) . ? C1 C2 1.509(2) . ? C2 C3 1.531(2) . ? C3 C4 1.537(2) . ? C5 C6 1.527(2) . ? O11 C12 1.3769(18) . ? O12 C15 1.3634(19) . ? O13 C17 1.3170(18) . ? O14 C17 1.2431(19) . ? C11 C16 1.401(2) . ? C11 C12 1.413(2) . ? C11 C17 1.480(2) . ? C12 C13 1.393(2) . ? C13 C14 1.390(2) . ? C14 C15 1.404(2) . ? C15 C16 1.388(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 C1 N1 C5 121.23(13) . . ? C1 N1 C4 113.45(13) . . ? C5 N1 C4 123.99(13) . . ? O1 C1 N1 123.55(15) . . ? O1 C1 C2 128.04(15) . . ? N1 C1 C2 108.38(14) . . ? C1 C2 C3 104.20(13) . . ? C2 C3 C4 103.69(13) . . ? N1 C4 C3 102.22(13) . . ? N1 C5 C6 112.72(13) . . ? O2 C6 N2 123.69(15) . . ? O2 C6 C5 121.09(14) . . ? N2 C6 C5 115.21(14) . . ? C16 C11 C12 119.35(14) . . ? C16 C11 C17 121.01(14) . . ? C12 C11 C17 119.63(14) . . ? O11 C12 C13 118.48(14) . . ? O11 C12 C11 122.11(14) . . ? C13 C12 C11 119.41(14) . . ? C14 C13 C12 120.48(14) . . ? C13 C14 C15 120.65(14) . . ? O12 C15 C16 118.36(14) . . ? O12 C15 C14 122.74(14) . . ? C16 C15 C14 118.90(15) . . ? C15 C16 C11 121.19(14) . . ? O14 C17 O13 122.63(14) . . ? O14 C17 C11 122.20(14) . . ? O13 C17 C11 115.17(13) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 C1 O1 3.9(2) . . . . ? C4 N1 C1 O1 171.33(14) . . . . ? C5 N1 C1 C2 -174.13(13) . . . . ? C4 N1 C1 C2 -6.75(18) . . . . ? O1 C1 C2 C3 170.08(16) . . . . ? N1 C1 C2 C3 -11.95(18) . . . . ? C1 C2 C3 C4 24.56(18) . . . . ? C1 N1 C4 C3 22.27(17) . . . . ? C5 N1 C4 C3 -170.75(14) . . . . ? C2 C3 C4 N1 -27.73(17) . . . . ? C1 N1 C5 C6 76.66(18) . . . . ? C4 N1 C5 C6 -89.35(18) . . . . ? N1 C5 C6 O2 5.2(2) . . . . ? N1 C5 C6 N2 -174.34(14) . . . . ? C16 C11 C12 O11 179.49(13) . . . . ? C17 C11 C12 O11 -1.4(2) . . . . ? C16 C11 C12 C13 -1.3(2) . . . . ? C17 C11 C12 C13 177.80(14) . . . . ? O11 C12 C13 C14 180.00(14) . . . . ? C11 C12 C13 C14 0.7(2) . . . . ? C12 C13 C14 C15 0.4(2) . . . . ? C13 C14 C15 O12 178.71(14) . . . . ? C13 C14 C15 C16 -1.1(2) . . . . ? O12 C15 C16 C11 -179.27(14) . . . . ? C14 C15 C16 C11 0.5(2) . . . . ? C12 C11 C16 C15 0.6(2) . . . . ? C17 C11 C16 C15 -178.42(14) . . . . ? C16 C11 C17 O14 179.36(14) . . . . ? C12 C11 C17 O14 0.3(2) . . . . ? C16 C11 C17 O13 0.2(2) . . . . ? C12 C11 C17 O13 -178.91(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 N2 H2AN O14 0.91 2.01 2.9074(18) 170.5 1_545 N2 H2BN O11 0.88 2.07 2.9440(19) 171.3 2_655 O11 H11O O14 0.88 1.83 2.5928(16) 143.3 . O12 H12O O1 0.89 1.79 2.6746(16) 173.7 6 O13 H13O O2 0.90 1.70 2.5899(15) 168.1 1_565 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.225 _refine_diff_density_min -0.181 _refine_diff_density_rms 0.044 data_jam624c _database_code_depnum_ccdc_archive 'CCDC 262606' _audit_creation_method SHELXL-97 _exptl_crystal_preparation Acetonitrile _chemical_name_systematic ; 1:1 Co-crystal of 2-Oxo-1-pyrrolidinyl)acetamide and 4-Hydroxybenzoic acid ; _chemical_name_common ;1:1 Co-crystal of 2-Oxo-1-pyrrolidinyl)acetamide and 4- Hydroxybenzoic acid ; _chemical_melting_point '416 K' _chemical_formula_moiety 'C6 H10 N2 O2, C7 H6 O3' _chemical_formula_sum 'C13 H16 N2 O5' _chemical_formula_weight 280.28 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/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 14.780(3) _cell_length_b 5.5029(12) _cell_length_c 17.068(4) _cell_angle_alpha 90.00 _cell_angle_beta 109.557(4) _cell_angle_gamma 90.00 _cell_volume 1308.0(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.423 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 0.110 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min 0.593 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4995 _diffrn_reflns_av_R_equivalents 0.0351 _diffrn_reflns_av_sigmaI/netI 0.0548 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 24.71 _reflns_number_total 2220 _reflns_number_gt 1753 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0508P)^2^+0.6752P] 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 2220 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0678 _refine_ls_R_factor_gt 0.0484 _refine_ls_wR_factor_ref 0.1347 _refine_ls_wR_factor_gt 0.1096 _refine_ls_goodness_of_fit_ref 1.108 _refine_ls_restrained_S_all 1.108 _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 O1 O 0.60789(12) 1.0575(3) 0.33150(11) 0.0195(5) Uani 1 1 d . . . O2 O 0.47465(13) 1.0571(3) 0.12739(11) 0.0218(5) Uani 1 1 d . . . N1 N 0.51418(15) 0.9202(4) 0.40243(13) 0.0201(5) Uani 1 1 d . . . H1NA H 0.4617 0.8182 0.4044 0.024 Uiso 1 1 d R . . H1NB H 0.5404 1.0338 0.4432 0.024 Uiso 1 1 d R . . N2 N 0.54241(15) 0.7234(4) 0.20741(13) 0.0152(5) Uani 1 1 d . . . C1 C 0.54368(17) 0.9212(5) 0.33739(15) 0.0153(6) Uani 1 1 d . . . C2 C 0.49385(18) 0.7457(5) 0.26755(15) 0.0161(6) Uani 1 1 d . . . H2A H 0.4903 0.5836 0.2916 0.019 Uiso 1 1 calc R . . H2B H 0.4273 0.8023 0.2391 0.019 Uiso 1 1 calc R . . C3 C 0.53243(18) 0.8859(5) 0.14605(15) 0.0163(6) Uani 1 1 d . . . C4 C 0.60459(19) 0.8267(5) 0.10418(17) 0.0206(7) Uani 1 1 d . . . H4A H 0.6582 0.9448 0.1200 0.025 Uiso 1 1 calc R . . H4B H 0.5742 0.8271 0.0429 0.025 Uiso 1 1 calc R . . C5 C 0.6399(2) 0.5723(5) 0.13603(17) 0.0216(7) Uani 1 1 d . . . H5A H 0.6021 0.4458 0.0977 0.026 Uiso 1 1 calc R . . H5B H 0.7086 0.5520 0.1427 0.026 Uiso 1 1 calc R . . C6 C 0.62425(19) 0.5596(5) 0.21999(17) 0.0209(6) Uani 1 1 d . . . H6A H 0.6087 0.3922 0.2325 0.025 Uiso 1 1 calc R . . H6B H 0.6815 0.6174 0.2655 0.025 Uiso 1 1 calc R . . O11 O 0.10268(13) 1.1728(3) 0.01491(11) 0.0198(5) Uani 1 1 d . . . O12 O 0.17878(12) 1.0713(3) -0.07377(11) 0.0213(5) Uani 1 1 d . . . H12O H 0.1497 1.2345 -0.1024 0.026 Uiso 1 1 d R . . O13 O 0.35592(12) 0.2636(3) 0.19497(11) 0.0194(5) Uani 1 1 d . . . H13O H 0.4010 0.1879 0.1721 0.023 Uiso 1 1 d R . . C11 C 0.20941(17) 0.8340(5) 0.04636(15) 0.0144(6) Uani 1 1 d . . . C12 C 0.27606(18) 0.6970(5) 0.02303(16) 0.0172(6) Uani 1 1 d . . . H12 H 0.2881 0.7373 -0.0267 0.021 Uiso 1 1 calc R . . C13 C 0.32480(18) 0.5043(5) 0.07075(16) 0.0176(6) Uani 1 1 d . . . H13 H 0.3695 0.4127 0.0537 0.021 Uiso 1 1 calc R . . C14 C 0.30781(17) 0.4460(5) 0.14386(15) 0.0158(6) Uani 1 1 d . . . C15 C 0.24136(18) 0.5788(5) 0.16830(15) 0.0163(6) Uani 1 1 d . . . H15 H 0.2292 0.5378 0.2180 0.020 Uiso 1 1 calc R . . C16 C 0.19324(17) 0.7705(5) 0.11963(15) 0.0156(6) Uani 1 1 d . . . H16 H 0.1482 0.8609 0.1365 0.019 Uiso 1 1 calc R . . C17 C 0.15879(17) 1.0405(5) -0.00416(15) 0.0146(6) 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 O1 0.0217(10) 0.0211(11) 0.0187(10) -0.0016(8) 0.0106(8) -0.0068(9) O2 0.0222(10) 0.0225(12) 0.0217(10) 0.0029(9) 0.0087(8) 0.0073(9) N1 0.0204(12) 0.0244(14) 0.0168(12) -0.0041(10) 0.0083(10) -0.0064(11) N2 0.0180(11) 0.0139(12) 0.0143(11) -0.0002(9) 0.0059(9) 0.0004(10) C1 0.0134(13) 0.0182(15) 0.0143(13) 0.0033(12) 0.0046(11) 0.0030(12) C2 0.0184(13) 0.0190(15) 0.0130(13) -0.0009(11) 0.0081(11) -0.0035(12) C3 0.0181(14) 0.0161(15) 0.0132(13) -0.0038(12) 0.0032(11) -0.0034(12) C4 0.0212(14) 0.0213(16) 0.0217(15) 0.0010(12) 0.0103(12) 0.0032(12) C5 0.0229(14) 0.0224(17) 0.0219(15) -0.0007(13) 0.0106(12) 0.0056(13) C6 0.0207(14) 0.0183(16) 0.0230(15) 0.0018(13) 0.0065(12) 0.0030(12) O11 0.0214(10) 0.0194(11) 0.0208(10) 0.0002(8) 0.0099(8) 0.0050(9) O12 0.0264(10) 0.0225(11) 0.0185(10) 0.0043(9) 0.0123(8) 0.0086(9) O13 0.0221(10) 0.0181(11) 0.0206(10) 0.0043(9) 0.0106(8) 0.0050(8) C11 0.0123(13) 0.0158(15) 0.0134(13) -0.0045(11) 0.0019(10) -0.0025(11) C12 0.0186(14) 0.0191(16) 0.0152(13) -0.0005(12) 0.0077(11) 0.0001(12) C13 0.0169(13) 0.0190(15) 0.0188(14) -0.0025(12) 0.0085(11) 0.0019(12) C14 0.0147(13) 0.0152(15) 0.0157(13) -0.0028(11) 0.0025(11) -0.0029(11) C15 0.0193(13) 0.0199(16) 0.0110(13) 0.0010(12) 0.0068(11) -0.0004(12) C16 0.0122(12) 0.0197(15) 0.0152(13) -0.0051(12) 0.0047(10) -0.0022(12) C17 0.0128(13) 0.0182(15) 0.0129(13) -0.0043(11) 0.0043(11) -0.0062(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 O1 C1 1.240(3) . ? O2 C3 1.240(3) . ? N1 C1 1.322(3) . ? N2 C3 1.347(3) . ? N2 C2 1.441(3) . ? N2 C6 1.465(3) . ? C1 C2 1.520(4) . ? C3 C4 1.505(4) . ? C4 C5 1.529(4) . ? C5 C6 1.528(4) . ? O11 C17 1.226(3) . ? O12 C17 1.328(3) . ? O13 C14 1.363(3) . ? C11 C16 1.394(4) . ? C11 C12 1.400(4) . ? C11 C17 1.470(4) . ? C12 C13 1.383(4) . ? C13 C14 1.390(4) . ? C14 C15 1.395(4) . ? C15 C16 1.383(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 C3 N2 C2 123.1(2) . . ? C3 N2 C6 113.1(2) . . ? C2 N2 C6 122.1(2) . . ? O1 C1 N1 123.2(2) . . ? O1 C1 C2 120.3(2) . . ? N1 C1 C2 116.5(2) . . ? N2 C2 C1 112.7(2) . . ? O2 C3 N2 126.2(2) . . ? O2 C3 C4 125.4(2) . . ? N2 C3 C4 108.3(2) . . ? C3 C4 C5 104.0(2) . . ? C6 C5 C4 103.6(2) . . ? N2 C6 C5 102.2(2) . . ? C16 C11 C12 117.9(2) . . ? C16 C11 C17 120.9(2) . . ? C12 C11 C17 121.2(2) . . ? C13 C12 C11 121.5(2) . . ? C12 C13 C14 119.4(2) . . ? O13 C14 C13 122.1(2) . . ? O13 C14 C15 117.6(2) . . ? C13 C14 C15 120.3(2) . . ? C16 C15 C14 119.5(2) . . ? C15 C16 C11 121.5(2) . . ? O11 C17 O12 122.3(2) . . ? O11 C17 C11 124.0(2) . . ? O12 C17 C11 113.7(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 C3 N2 C2 C1 -80.7(3) . . . . ? C6 N2 C2 C1 83.5(3) . . . . ? O1 C1 C2 N2 12.2(3) . . . . ? N1 C1 C2 N2 -168.4(2) . . . . ? C2 N2 C3 O2 -8.0(4) . . . . ? C6 N2 C3 O2 -173.5(2) . . . . ? C2 N2 C3 C4 171.2(2) . . . . ? C6 N2 C3 C4 5.8(3) . . . . ? O2 C3 C4 C5 -167.2(2) . . . . ? N2 C3 C4 C5 13.5(3) . . . . ? C3 C4 C5 C6 -26.3(3) . . . . ? C3 N2 C6 C5 -22.5(3) . . . . ? C2 N2 C6 C5 172.0(2) . . . . ? C4 C5 C6 N2 28.9(3) . . . . ? C16 C11 C12 C13 0.0(4) . . . . ? C17 C11 C12 C13 179.2(2) . . . . ? C11 C12 C13 C14 -0.4(4) . . . . ? C12 C13 C14 O13 -177.7(2) . . . . ? C12 C13 C14 C15 0.8(4) . . . . ? O13 C14 C15 C16 177.9(2) . . . . ? C13 C14 C15 C16 -0.7(4) . . . . ? C14 C15 C16 C11 0.2(4) . . . . ? C12 C11 C16 C15 0.2(4) . . . . ? C17 C11 C16 C15 -179.1(2) . . . . ? C16 C11 C17 O11 2.3(4) . . . . ? C12 C11 C17 O11 -176.9(2) . . . . ? C16 C11 C17 O12 -177.2(2) . . . . ? C12 C11 C17 O12 3.5(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 H1NA O11 0.97 2.08 2.908(3) 142.9 2_545 N1 H1NB O11 0.92 2.05 2.955(3) 168.4 4_686 O12 H12O O1 1.04 1.58 2.598(3) 163.5 4_585 O13 H13O O2 0.97 1.69 2.656(2) 176.9 1_545 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 24.71 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.226 _refine_diff_density_min -0.230 _refine_diff_density_rms 0.058