# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Shan, Ning' 'Weyna, David' 'Cheney, Miranda' 'Hanna, Mazen' 'Wojtas, Lukasz' 'Zaworotko , Michael' _publ_contact_author_name 'Dr Ning Shan' _publ_contact_author_email nshan@tharpharma.com _publ_contact_author_phone 813-978-3980 _publ_section_title ; Crystal Engineering of Multiple-Component Organic Solids: Pharmaceutical Cocrystals of Tadalafil with Persistent Hydrogen Bonding Motifs ; # Attachment '- TDF cocrystals cif file 20111123.cif' #TrackingRef '- TDF cocrystals cif file 20111123.cif' ########################################################## data_TDF_MPB_1 _database_code_depnum_ccdc_archive 'CCDC 855598' #TrackingRef '- TDF cocrystals cif file 20111123.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'tadalafil methylparaben' _chemical_melting_point 460.09 _chemical_formula_moiety 'C22 H19 N3 O4, C8 H8 O3' _chemical_formula_sum 'C30 H27 N3 O7' _chemical_formula_weight 541.55 _chemical_absolute_configuration syn loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.4455(3) _cell_length_b 7.8767(2) _cell_length_c 17.2532(5) _cell_angle_alpha 90.00 _cell_angle_beta 98.352(2) _cell_angle_gamma 90.00 _cell_volume 1270.01(6) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4051 _cell_measurement_theta_min 4.73 _cell_measurement_theta_max 67.3 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.416 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.844 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6775 _exptl_absorpt_correction_T_max 0.9590 _exptl_absorpt_process_details 'SADABS; (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART APEXII CCD' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8383 _diffrn_reflns_av_R_equivalents 0.0292 _diffrn_reflns_av_sigmaI/netI 0.0369 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.59 _diffrn_reflns_theta_max 65.93 _reflns_number_total 3531 _reflns_number_gt 3234 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2010)' _computing_cell_refinement 'APEX2 (Bruker, 2010); SAINT (Bruker, 2009)' _computing_data_reduction 'SAINT (Bruker, 2009);XPREP(Sheldrick,2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material 'APEX2 (Bruker, 2010)' _publ_section_references ; Bruker AXS. (2010). APEX2 Bruker AXS, Inc. Madison, Wisconsin, USA. Bruker AXS. (2009). SAINT Bruker AXS, Inc. Madison, Wisconsin, USA. Sheldrick, G. M. (2008). SADABS. University of G\"ottingen, Germany. Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122. ; _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^)+(0.0526P)^2^+0.1325P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.02(19) _refine_ls_number_reflns 3531 _refine_ls_number_parameters 363 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0393 _refine_ls_R_factor_gt 0.0349 _refine_ls_wR_factor_ref 0.0888 _refine_ls_wR_factor_gt 0.0864 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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 C1 C 0.2529(3) 0.9348(3) 1.05894(14) 0.0275(6) Uani 1 1 d . . . H1 H 0.2741 0.9992 1.1057 0.033 Uiso 1 1 calc R . . C2 C 0.3283(3) 0.7456(4) 0.96277(15) 0.0277(6) Uani 1 1 d . . . H2 H 0.4006 0.6807 0.9436 0.033 Uiso 1 1 calc R . . C3 C 0.1908(3) 0.7482(3) 0.92267(14) 0.0254(6) Uani 1 1 d . . . H3 H 0.1692 0.6839 0.8759 0.031 Uiso 1 1 calc R . . C4 C 0.0835(3) 0.8423(4) 0.94906(14) 0.0249(5) Uani 1 1 d . . . C5 C 0.1159(3) 0.9353(3) 1.01753(15) 0.0274(6) Uani 1 1 d . . . H5 H 0.0432 1.0002 1.0363 0.033 Uiso 1 1 calc R . . C6 C 0.3598(3) 0.8390(4) 1.03146(14) 0.0266(6) Uani 1 1 d . . . C7 C -0.0615(3) 0.8381(4) 0.90373(14) 0.0267(6) Uani 1 1 d . . . C8 C -0.3018(3) 0.9262(5) 0.8955(2) 0.0494(9) Uani 1 1 d . . . H8A H -0.3313 0.8099 0.8807 0.074 Uiso 1 1 calc R . . H8B H -0.3042 0.9956 0.8482 0.074 Uiso 1 1 calc R . . H8C H -0.3673 0.9742 0.9288 0.074 Uiso 1 1 calc R . . C9 C 0.1351(3) 1.2831(4) 0.84791(15) 0.0290(6) Uani 1 1 d . . . H9 H 0.1661 1.3414 0.8956 0.035 Uiso 1 1 calc R . . C10 C 0.0129(3) 1.3399(4) 0.79874(15) 0.0299(6) Uani 1 1 d . . . H10 H -0.0378 1.4355 0.8140 0.036 Uiso 1 1 calc R . . C11 C -0.0352(3) 1.2596(4) 0.72853(14) 0.0271(6) Uani 1 1 d . . . H11 H -0.1188 1.2974 0.6957 0.033 Uiso 1 1 calc R . . C12 C 0.0430(3) 1.1215(4) 0.70762(14) 0.0238(6) Uani 1 1 d . . . C13 C 0.1654(2) 1.0610(3) 0.75693(14) 0.0214(6) Uani 1 1 d . . . C14 C 0.2110(3) 1.1441(4) 0.82823(14) 0.0257(6) Uani 1 1 d . . . H14 H 0.2927 1.1052 0.8623 0.031 Uiso 1 1 calc R . . C15 C 0.2170(2) 0.9177(3) 0.71747(14) 0.0208(5) Uani 1 1 d . . . C16 C 0.1287(2) 0.8996(3) 0.64878(13) 0.0197(5) Uani 1 1 d . . . C17 C 0.3350(2) 0.7933(3) 0.74093(14) 0.0220(5) Uani 1 1 d . . . H17A H 0.3563 0.7861 0.7987 0.026 Uiso 1 1 calc R . . H17B H 0.4229 0.8299 0.7206 0.026 Uiso 1 1 calc R . . C18 C 0.2862(2) 0.6205(3) 0.70673(13) 0.0213(5) Uani 1 1 d . . . H18 H 0.2020 0.5840 0.7317 0.026 Uiso 1 1 calc R . . C19 C 0.1522(2) 0.7782(3) 0.58517(14) 0.0200(5) Uani 1 1 d . . . H19 H 0.0573 0.7355 0.5593 0.024 Uiso 1 1 calc R . . C20 C 0.2249(2) 0.8734(3) 0.52460(13) 0.0191(5) Uani 1 1 d . . . C21 C 0.1369(2) 0.9399(3) 0.45913(14) 0.0217(6) Uani 1 1 d . . . H21 H 0.0377 0.9139 0.4488 0.026 Uiso 1 1 calc R . . C22 C 0.2007(2) 1.0440(3) 0.41083(14) 0.0212(5) Uani 1 1 d . . . C23 C 0.3455(2) 1.0805(3) 0.42373(14) 0.0205(5) Uani 1 1 d . . . C24 C 0.2498(3) 1.2079(4) 0.31258(17) 0.0362(7) Uani 1 1 d . . . H24A H 0.2289 1.3303 0.3043 0.043 Uiso 1 1 calc R . . H24B H 0.2597 1.1562 0.2613 0.043 Uiso 1 1 calc R . . C25 C 0.4340(2) 1.0135(3) 0.48651(13) 0.0222(5) Uani 1 1 d . . . H25 H 0.5338 1.0365 0.4950 0.027 Uiso 1 1 calc R . . C26 C 0.3699(2) 0.9099(3) 0.53739(13) 0.0208(5) Uani 1 1 d . . . H26 H 0.4275 0.8631 0.5820 0.025 Uiso 1 1 calc R . . C27 C 0.2416(2) 0.4960(3) 0.57415(13) 0.0198(5) Uani 1 1 d . . . C28 C 0.3096(3) 0.3358(3) 0.61035(14) 0.0239(5) Uani 1 1 d . . . H28A H 0.2335 0.2615 0.6253 0.029 Uiso 1 1 calc R . . H28B H 0.3554 0.2748 0.5703 0.029 Uiso 1 1 calc R . . C29 C 0.5236(3) 0.2313(4) 0.69828(17) 0.0323(7) Uani 1 1 d . . . H29A H 0.4779 0.1292 0.7156 0.048 Uiso 1 1 calc R . . H29B H 0.5969 0.2714 0.7404 0.048 Uiso 1 1 calc R . . H29C H 0.5682 0.2045 0.6519 0.048 Uiso 1 1 calc R . . C30 C 0.4043(2) 0.4908(3) 0.72828(14) 0.0229(5) Uani 1 1 d . . . N1 N 0.4160(2) 0.3635(3) 0.67883(12) 0.0240(5) Uani 1 1 d . . . N2 N 0.23860(19) 0.6316(3) 0.62040(11) 0.0207(5) Uani 1 1 d . . . N3 N 0.0229(2) 1.0204(3) 0.64120(11) 0.0219(5) Uani 1 1 d . . . H3A H -0.0456 1.0316 0.6012 0.026 Uiso 1 1 calc R . . O1 O 0.49564(18) 0.8302(3) 1.07026(11) 0.0334(5) Uani 1 1 d . . . H1O H 0.4914 0.8786 1.1192 0.050 Uiso 1 1 d R . . O2 O -0.0924(2) 0.7634(3) 0.84216(11) 0.0371(5) Uani 1 1 d . . . O3 O -0.15845(19) 0.9244(3) 0.93775(11) 0.0366(5) Uani 1 1 d . . . O4 O 0.37937(17) 1.1865(2) 0.36577(10) 0.0264(4) Uani 1 1 d . . . O5 O 0.13661(17) 1.1279(2) 0.34501(10) 0.0270(4) Uani 1 1 d . . . O6 O 0.18920(16) 0.4942(2) 0.50414(9) 0.0232(4) Uani 1 1 d . . . O7 O 0.48460(18) 0.5080(2) 0.79168(10) 0.0303(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0325(14) 0.0271(16) 0.0211(13) -0.0056(11) -0.0016(11) -0.0020(11) C2 0.0317(14) 0.0275(17) 0.0247(13) -0.0010(11) 0.0066(11) 0.0019(12) C3 0.0337(14) 0.0240(15) 0.0182(12) -0.0023(10) 0.0020(10) -0.0063(11) C4 0.0296(13) 0.0252(15) 0.0192(12) 0.0019(11) 0.0015(10) -0.0044(11) C5 0.0317(13) 0.0240(16) 0.0261(13) -0.0036(11) 0.0031(11) 0.0021(11) C6 0.0259(13) 0.0285(16) 0.0237(13) 0.0025(11) -0.0016(10) -0.0028(11) C7 0.0342(14) 0.0236(15) 0.0213(13) 0.0022(11) 0.0009(11) -0.0013(11) C8 0.0288(15) 0.052(2) 0.062(2) -0.0148(18) -0.0118(14) 0.0096(15) C9 0.0369(14) 0.0290(17) 0.0204(12) -0.0021(11) 0.0021(11) 0.0000(12) C10 0.0372(14) 0.0249(16) 0.0283(14) -0.0010(11) 0.0069(11) 0.0074(12) C11 0.0273(13) 0.0309(17) 0.0224(13) 0.0028(11) 0.0012(10) 0.0037(12) C12 0.0261(12) 0.0246(15) 0.0210(12) 0.0024(11) 0.0043(10) 0.0000(11) C13 0.0208(12) 0.0217(15) 0.0220(12) 0.0026(10) 0.0044(10) -0.0033(9) C14 0.0264(12) 0.0281(16) 0.0221(13) 0.0029(10) 0.0019(10) 0.0018(11) C15 0.0172(11) 0.0243(15) 0.0211(12) 0.0010(10) 0.0028(9) -0.0016(10) C16 0.0183(12) 0.0220(15) 0.0191(12) 0.0010(10) 0.0035(9) 0.0006(9) C17 0.0213(12) 0.0286(16) 0.0161(11) 0.0003(10) 0.0021(9) 0.0002(10) C18 0.0196(11) 0.0265(15) 0.0170(12) 0.0029(10) -0.0001(9) 0.0024(10) C19 0.0165(11) 0.0206(14) 0.0219(12) 0.0009(10) -0.0005(9) 0.0011(10) C20 0.0214(12) 0.0162(14) 0.0193(11) -0.0035(9) 0.0012(9) 0.0015(9) C21 0.0158(11) 0.0259(16) 0.0224(12) -0.0012(10) -0.0011(9) -0.0007(10) C22 0.0207(12) 0.0216(15) 0.0199(12) 0.0002(10) -0.0018(10) 0.0029(10) C23 0.0222(12) 0.0203(15) 0.0198(12) -0.0032(10) 0.0055(10) -0.0008(10) C24 0.0274(14) 0.045(2) 0.0348(15) 0.0191(13) -0.0018(12) -0.0051(12) C25 0.0161(11) 0.0278(15) 0.0221(12) -0.0028(11) 0.0006(9) 0.0005(10) C26 0.0226(12) 0.0223(14) 0.0163(12) -0.0019(10) -0.0010(9) 0.0041(10) C27 0.0140(10) 0.0244(15) 0.0212(12) -0.0017(10) 0.0030(9) -0.0027(10) C28 0.0229(12) 0.0229(15) 0.0250(13) -0.0026(10) 0.0005(10) -0.0015(10) C29 0.0305(14) 0.0264(17) 0.0375(16) 0.0001(11) -0.0038(12) 0.0055(11) C30 0.0208(12) 0.0242(15) 0.0238(13) 0.0046(11) 0.0040(10) -0.0008(11) N1 0.0236(10) 0.0219(13) 0.0251(11) 0.0016(9) -0.0004(9) 0.0036(9) N2 0.0191(10) 0.0228(13) 0.0195(10) 0.0005(9) 0.0007(8) 0.0015(8) N3 0.0208(10) 0.0260(13) 0.0176(10) 0.0003(9) -0.0013(8) 0.0033(9) O1 0.0278(9) 0.0416(13) 0.0284(10) -0.0047(9) -0.0038(8) 0.0015(8) O2 0.0346(10) 0.0438(13) 0.0296(10) -0.0084(9) -0.0068(8) 0.0018(9) O3 0.0287(10) 0.0398(13) 0.0378(11) -0.0125(9) -0.0073(8) 0.0055(9) O4 0.0227(9) 0.0327(12) 0.0221(9) 0.0058(8) -0.0023(7) -0.0079(8) O5 0.0234(8) 0.0330(12) 0.0226(9) 0.0077(8) -0.0029(7) -0.0024(8) O6 0.0195(8) 0.0285(10) 0.0211(9) -0.0015(7) 0.0009(6) -0.0001(7) O7 0.0344(10) 0.0277(11) 0.0251(9) 0.0018(8) -0.0084(8) 0.0035(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 C1 C5 1.384(3) . ? C1 C6 1.397(4) . ? C1 H1 0.9500 . ? C2 C3 1.380(4) . ? C2 C6 1.390(4) . ? C2 H2 0.9500 . ? C3 C4 1.385(4) . ? C3 H3 0.9500 . ? C4 C5 1.386(3) . ? C4 C7 1.476(3) . ? C5 H5 0.9500 . ? C6 O1 1.360(3) . ? C7 O2 1.212(3) . ? C7 O3 1.342(3) . ? C8 O3 1.441(3) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C14 1.378(4) . ? C9 C10 1.403(4) . ? C9 H9 0.9500 . ? C10 C11 1.384(4) . ? C10 H10 0.9500 . ? C11 C12 1.391(4) . ? C11 H11 0.9500 . ? C12 N3 1.386(3) . ? C12 C13 1.415(3) . ? C13 C14 1.405(4) . ? C13 C15 1.439(4) . ? C14 H14 0.9500 . ? C15 C16 1.354(3) . ? C15 C17 1.495(3) . ? C16 N3 1.372(3) . ? C16 C19 1.496(3) . ? C17 C18 1.528(3) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 N2 1.495(3) . ? C18 C30 1.518(3) . ? C18 H18 1.0000 . ? C19 N2 1.492(3) . ? C19 C20 1.528(3) . ? C19 H19 1.0000 . ? C20 C26 1.386(3) . ? C20 C21 1.403(3) . ? C21 C22 1.370(4) . ? C21 H21 0.9500 . ? C22 O5 1.376(3) . ? C22 C23 1.383(3) . ? C23 C25 1.373(3) . ? C23 O4 1.376(3) . ? C24 O5 1.424(3) . ? C24 O4 1.429(3) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 C26 1.399(4) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 O6 1.237(3) . ? C27 N2 1.336(3) . ? C27 C28 1.510(4) . ? C28 N1 1.452(3) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 N1 1.460(3) . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 O7 1.244(3) . ? C30 N1 1.332(3) . ? N3 H3A 0.8800 . ? O1 H1O 0.9327 . ? 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 C5 C1 C6 119.6(2) . . ? C5 C1 H1 120.2 . . ? C6 C1 H1 120.2 . . ? C3 C2 C6 119.3(2) . . ? C3 C2 H2 120.4 . . ? C6 C2 H2 120.4 . . ? C2 C3 C4 121.5(2) . . ? C2 C3 H3 119.2 . . ? C4 C3 H3 119.2 . . ? C3 C4 C5 118.8(2) . . ? C3 C4 C7 118.7(2) . . ? C5 C4 C7 122.5(2) . . ? C1 C5 C4 120.8(2) . . ? C1 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? O1 C6 C2 117.5(2) . . ? O1 C6 C1 122.5(2) . . ? C2 C6 C1 120.0(2) . . ? O2 C7 O3 122.4(2) . . ? O2 C7 C4 124.2(2) . . ? O3 C7 C4 113.4(2) . . ? O3 C8 H8A 109.5 . . ? O3 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? O3 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C14 C9 C10 121.1(2) . . ? C14 C9 H9 119.5 . . ? C10 C9 H9 119.5 . . ? C11 C10 C9 121.4(3) . . ? C11 C10 H10 119.3 . . ? C9 C10 H10 119.3 . . ? C10 C11 C12 117.7(2) . . ? C10 C11 H11 121.1 . . ? C12 C11 H11 121.1 . . ? N3 C12 C11 130.5(2) . . ? N3 C12 C13 107.8(2) . . ? C11 C12 C13 121.7(2) . . ? C14 C13 C12 119.3(2) . . ? C14 C13 C15 134.3(2) . . ? C12 C13 C15 106.4(2) . . ? C9 C14 C13 118.8(2) . . ? C9 C14 H14 120.6 . . ? C13 C14 H14 120.6 . . ? C16 C15 C13 106.8(2) . . ? C16 C15 C17 120.6(2) . . ? C13 C15 C17 132.5(2) . . ? C15 C16 N3 111.0(2) . . ? C15 C16 C19 124.8(2) . . ? N3 C16 C19 123.8(2) . . ? C15 C17 C18 107.93(19) . . ? C15 C17 H17A 110.1 . . ? C18 C17 H17A 110.1 . . ? C15 C17 H17B 110.1 . . ? C18 C17 H17B 110.1 . . ? H17A C17 H17B 108.4 . . ? N2 C18 C30 112.8(2) . . ? N2 C18 C17 111.28(19) . . ? C30 C18 C17 109.57(19) . . ? N2 C18 H18 107.7 . . ? C30 C18 H18 107.7 . . ? C17 C18 H18 107.7 . . ? N2 C19 C16 109.06(19) . . ? N2 C19 C20 112.65(19) . . ? C16 C19 C20 108.5(2) . . ? N2 C19 H19 108.9 . . ? C16 C19 H19 108.9 . . ? C20 C19 H19 108.9 . . ? C26 C20 C21 120.5(2) . . ? C26 C20 C19 121.7(2) . . ? C21 C20 C19 117.5(2) . . ? C22 C21 C20 116.9(2) . . ? C22 C21 H21 121.6 . . ? C20 C21 H21 121.6 . . ? C21 C22 O5 127.6(2) . . ? C21 C22 C23 122.6(2) . . ? O5 C22 C23 109.8(2) . . ? C25 C23 O4 128.9(2) . . ? C25 C23 C22 121.4(2) . . ? O4 C23 C22 109.8(2) . . ? O5 C24 O4 108.5(2) . . ? O5 C24 H24A 110.0 . . ? O4 C24 H24A 110.0 . . ? O5 C24 H24B 110.0 . . ? O4 C24 H24B 110.0 . . ? H24A C24 H24B 108.4 . . ? C23 C25 C26 116.7(2) . . ? C23 C25 H25 121.6 . . ? C26 C25 H25 121.6 . . ? C20 C26 C25 121.9(2) . . ? C20 C26 H26 119.0 . . ? C25 C26 H26 119.0 . . ? O6 C27 N2 123.5(2) . . ? O6 C27 C28 118.7(2) . . ? N2 C27 C28 117.8(2) . . ? N1 C28 C27 114.4(2) . . ? N1 C28 H28A 108.6 . . ? C27 C28 H28A 108.6 . . ? N1 C28 H28B 108.6 . . ? C27 C28 H28B 108.6 . . ? H28A C28 H28B 107.6 . . ? N1 C29 H29A 109.5 . . ? N1 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? N1 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? O7 C30 N1 123.3(2) . . ? O7 C30 C18 118.3(2) . . ? N1 C30 C18 118.4(2) . . ? C30 N1 C28 121.5(2) . . ? C30 N1 C29 120.6(2) . . ? C28 N1 C29 117.1(2) . . ? C27 N2 C19 115.69(19) . . ? C27 N2 C18 121.3(2) . . ? C19 N2 C18 121.27(19) . . ? C16 N3 C12 108.03(19) . . ? C16 N3 H3A 126.0 . . ? C12 N3 H3A 126.0 . . ? C6 O1 H1O 105.3 . . ? C7 O3 C8 115.7(2) . . ? C23 O4 C24 105.71(18) . . ? C22 O5 C24 105.75(18) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C2 C3 C4 0.3(4) . . . . ? C2 C3 C4 C5 -0.2(4) . . . . ? C2 C3 C4 C7 -179.4(2) . . . . ? C6 C1 C5 C4 -0.2(4) . . . . ? C3 C4 C5 C1 0.1(4) . . . . ? C7 C4 C5 C1 179.3(3) . . . . ? C3 C2 C6 O1 178.5(2) . . . . ? C3 C2 C6 C1 -0.4(4) . . . . ? C5 C1 C6 O1 -178.5(3) . . . . ? C5 C1 C6 C2 0.3(4) . . . . ? C3 C4 C7 O2 -3.7(4) . . . . ? C5 C4 C7 O2 177.1(3) . . . . ? C3 C4 C7 O3 175.6(2) . . . . ? C5 C4 C7 O3 -3.6(4) . . . . ? C14 C9 C10 C11 -0.5(4) . . . . ? C9 C10 C11 C12 -0.9(4) . . . . ? C10 C11 C12 N3 -178.3(3) . . . . ? C10 C11 C12 C13 1.7(4) . . . . ? N3 C12 C13 C14 178.9(2) . . . . ? C11 C12 C13 C14 -1.2(4) . . . . ? N3 C12 C13 C15 -0.7(3) . . . . ? C11 C12 C13 C15 179.3(2) . . . . ? C10 C9 C14 C13 1.1(4) . . . . ? C12 C13 C14 C9 -0.3(4) . . . . ? C15 C13 C14 C9 179.1(3) . . . . ? C14 C13 C15 C16 -178.8(3) . . . . ? C12 C13 C15 C16 0.7(3) . . . . ? C14 C13 C15 C17 5.3(5) . . . . ? C12 C13 C15 C17 -175.3(3) . . . . ? C13 C15 C16 N3 -0.5(3) . . . . ? C17 C15 C16 N3 176.1(2) . . . . ? C13 C15 C16 C19 172.8(2) . . . . ? C17 C15 C16 C19 -10.6(4) . . . . ? C16 C15 C17 C18 -31.2(3) . . . . ? C13 C15 C17 C18 144.3(3) . . . . ? C15 C17 C18 N2 53.7(2) . . . . ? C15 C17 C18 C30 179.17(19) . . . . ? C15 C16 C19 N2 26.7(3) . . . . ? N3 C16 C19 N2 -160.8(2) . . . . ? C15 C16 C19 C20 -96.3(3) . . . . ? N3 C16 C19 C20 76.1(3) . . . . ? N2 C19 C20 C26 -42.8(3) . . . . ? C16 C19 C20 C26 78.0(3) . . . . ? N2 C19 C20 C21 144.2(2) . . . . ? C16 C19 C20 C21 -94.9(2) . . . . ? C26 C20 C21 C22 -1.6(4) . . . . ? C19 C20 C21 C22 171.5(2) . . . . ? C20 C21 C22 O5 -177.8(2) . . . . ? C20 C21 C22 C23 1.5(4) . . . . ? C21 C22 C23 C25 -0.1(4) . . . . ? O5 C22 C23 C25 179.4(2) . . . . ? C21 C22 C23 O4 179.5(2) . . . . ? O5 C22 C23 O4 -1.1(3) . . . . ? O4 C23 C25 C26 179.3(2) . . . . ? C22 C23 C25 C26 -1.3(4) . . . . ? C21 C20 C26 C25 0.2(4) . . . . ? C19 C20 C26 C25 -172.5(2) . . . . ? C23 C25 C26 C20 1.2(4) . . . . ? O6 C27 C28 N1 155.9(2) . . . . ? N2 C27 C28 N1 -25.6(3) . . . . ? N2 C18 C30 O7 156.2(2) . . . . ? C17 C18 C30 O7 31.6(3) . . . . ? N2 C18 C30 N1 -24.5(3) . . . . ? C17 C18 C30 N1 -149.0(2) . . . . ? O7 C30 N1 C28 172.1(2) . . . . ? C18 C30 N1 C28 -7.2(3) . . . . ? O7 C30 N1 C29 2.0(4) . . . . ? C18 C30 N1 C29 -177.3(2) . . . . ? C27 C28 N1 C30 33.0(3) . . . . ? C27 C28 N1 C29 -156.5(2) . . . . ? O6 C27 N2 C19 6.9(3) . . . . ? C28 C27 N2 C19 -171.51(19) . . . . ? O6 C27 N2 C18 171.9(2) . . . . ? C28 C27 N2 C18 -6.5(3) . . . . ? C16 C19 N2 C27 165.81(19) . . . . ? C20 C19 N2 C27 -73.7(2) . . . . ? C16 C19 N2 C18 0.8(3) . . . . ? C20 C19 N2 C18 121.4(2) . . . . ? C30 C18 N2 C27 31.6(3) . . . . ? C17 C18 N2 C27 155.2(2) . . . . ? C30 C18 N2 C19 -164.3(2) . . . . ? C17 C18 N2 C19 -40.6(3) . . . . ? C15 C16 N3 C12 0.1(3) . . . . ? C19 C16 N3 C12 -173.3(2) . . . . ? C11 C12 N3 C16 -179.5(3) . . . . ? C13 C12 N3 C16 0.4(3) . . . . ? O2 C7 O3 C8 -1.4(4) . . . . ? C4 C7 O3 C8 179.3(3) . . . . ? C25 C23 O4 C24 176.2(3) . . . . ? C22 C23 O4 C24 -3.2(3) . . . . ? O5 C24 O4 C23 6.3(3) . . . . ? C21 C22 O5 C24 -175.6(3) . . . . ? C23 C22 O5 C24 5.0(3) . . . . ? O4 C24 O5 C22 -7.0(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 N3 H3A O6 0.88 2.12 2.981(2) 164.4 2_556 O1 H1O O7 0.93 1.83 2.746(3) 166.3 2_657 _diffrn_measured_fraction_theta_max 0.954 _diffrn_reflns_theta_full 65.93 _diffrn_measured_fraction_theta_full 0.954 _refine_diff_density_max 0.171 _refine_diff_density_min -0.185 _refine_diff_density_rms 0.038 #===END ########################################################## data_TDF_PPB_2 _database_code_depnum_ccdc_archive 'CCDC 855599' #TrackingRef '- TDF cocrystals cif file 20111123.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'tadalafil propylparaben' _chemical_melting_point 422.21 _chemical_formula_moiety 'C22 H19 N3 O4, C10 H12 O3' _chemical_formula_sum 'C32 H31 N3 O7' _chemical_formula_weight 569.60 _chemical_absolute_configuration syn loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.3357(2) _cell_length_b 8.3056(2) _cell_length_c 17.3542(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.854(2) _cell_angle_gamma 90.00 _cell_volume 1345.47(6) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1885 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 65.2 _exptl_crystal_description block _exptl_crystal_colour colorles _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.29 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.406 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600 _exptl_absorpt_coefficient_mu 0.824 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7340 _exptl_absorpt_correction_T_max 0.7961 _exptl_absorpt_process_details 'SADABS; (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART APEXII CCD' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6565 _diffrn_reflns_av_R_equivalents 0.0358 _diffrn_reflns_av_sigmaI/netI 0.0537 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.55 _diffrn_reflns_theta_max 65.80 _reflns_number_total 3847 _reflns_number_gt 3434 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2010)' _computing_cell_refinement 'APEX2 (Bruker, 2010); SAINT (Bruker, 2009)' _computing_data_reduction 'SAINT (Bruker, 2009);XPREP(Sheldrick,2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material 'APEX2 (Bruker, 2010)' _publ_section_references ; Bruker AXS. (2010). APEX2 Bruker AXS, Inc. Madison, Wisconsin, USA. Bruker AXS. (2009). SAINT Bruker AXS, Inc. Madison, Wisconsin, USA. Sheldrick, G. M. (2008). SADABS. University of G\"ottingen, Germany. Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122. ; _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^)+(0.0538P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.1(2) _refine_ls_number_reflns 3847 _refine_ls_number_parameters 382 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0478 _refine_ls_R_factor_gt 0.0410 _refine_ls_wR_factor_ref 0.1002 _refine_ls_wR_factor_gt 0.0963 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _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 1.06188(19) 0.0894(3) 0.53568(11) 0.0240(5) Uani 1 1 d . . . O1 O 0.43317(19) 0.0361(3) 0.40433(11) 0.0243(5) Uani 1 1 d . . . H1 H 0.4372 0.1007 0.3672 0.036 Uiso 1 1 calc R . . O2 O 0.9754(2) -0.0823(3) 0.62373(12) 0.0252(5) Uani 1 1 d . . . C4 C 0.8200(3) 0.0193(4) 0.52411(16) 0.0183(6) Uani 1 1 d . . . C9 C 1.2262(3) 0.1845(4) 0.63732(17) 0.0251(7) Uani 1 1 d . . . H9A H 1.1601 0.1538 0.6789 0.030 Uiso 1 1 calc R . . H9B H 1.2043 0.2967 0.6219 0.030 Uiso 1 1 calc R . . C6 C 0.5747(3) -0.0669(4) 0.50610(17) 0.0213(7) Uani 1 1 d . . . H6 H 0.4956 -0.1300 0.5219 0.026 Uiso 1 1 calc R . . C3 C 0.8051(3) 0.1201(4) 0.46100(16) 0.0191(6) Uani 1 1 d . . . H3 H 0.8835 0.1850 0.4458 0.023 Uiso 1 1 calc R . . C8 C 1.2042(3) 0.0739(4) 0.56920(17) 0.0242(7) Uani 1 1 d . . . H8A H 1.2760 0.0991 0.5296 0.029 Uiso 1 1 calc R . . H8B H 1.2195 -0.0389 0.5859 0.029 Uiso 1 1 calc R . . C2 C 0.6774(3) 0.1273(4) 0.41983(16) 0.0206(7) Uani 1 1 d . . . H2 H 0.6688 0.1959 0.3762 0.025 Uiso 1 1 calc R . . C1 C 0.5611(3) 0.0338(4) 0.44240(15) 0.0204(7) Uani 1 1 d . . . C7 C 0.9576(3) 0.0028(4) 0.56779(16) 0.0214(7) Uani 1 1 d . . . C5 C 0.7030(3) -0.0752(4) 0.54649(17) 0.0217(7) Uani 1 1 d . . . H5 H 0.7121 -0.1452 0.5896 0.026 Uiso 1 1 calc R . . C10 C 1.3810(3) 0.1736(5) 0.66694(19) 0.0307(8) Uani 1 1 d . . . H10A H 1.4053 0.0609 0.6774 0.046 Uiso 1 1 calc R . . H10B H 1.3915 0.2365 0.7145 0.046 Uiso 1 1 calc R . . H10C H 1.4455 0.2166 0.6279 0.046 Uiso 1 1 calc R . . C18 C 0.0977(3) 0.6165(4) 0.14612(16) 0.0181(6) Uani 1 1 d . . . C22 C 0.3607(3) 0.2268(4) 0.22032(16) 0.0217(7) Uani 1 1 d . . . C31 C 0.1428(3) 0.6540(4) -0.04101(16) 0.0199(6) Uani 1 1 d . . . H33 H 0.0469 0.6210 -0.0512 0.024 Uiso 1 1 calc R . . C24 C 0.2843(3) 0.0816(4) 0.10439(17) 0.0234(7) Uani 1 1 d . . . H24A H 0.2031 0.0131 0.1201 0.028 Uiso 1 1 calc R . . H24B H 0.3371 0.0228 0.0641 0.028 Uiso 1 1 calc R . . C20 C 0.1351(3) 0.5018(4) 0.08339(16) 0.0203(7) Uani 1 1 d . . . H20 H 0.0447 0.4607 0.0588 0.024 Uiso 1 1 calc R . . C15 C 0.0102(3) 0.8381(4) 0.20163(16) 0.0210(7) Uani 1 1 d . . . C16 C 0.1209(3) 0.7757(4) 0.25013(15) 0.0181(6) Uani 1 1 d . . . C28 C 0.4287(3) 0.7502(4) -0.01386(15) 0.0203(6) Uani 1 1 d . . . H28 H 0.5254 0.7819 -0.0053 0.024 Uiso 1 1 calc R . . C29 C 0.3509(3) 0.8069(4) -0.07567(16) 0.0211(7) Uani 1 1 d . . . C27 C 0.3603(3) 0.6436(4) 0.03626(16) 0.0203(7) Uani 1 1 d . . . H27 H 0.4113 0.6028 0.0798 0.024 Uiso 1 1 calc R . . C21 C 0.2449(3) 0.3515(4) 0.20083(16) 0.0208(7) Uani 1 1 d . . . H21 H 0.1543 0.3150 0.2254 0.025 Uiso 1 1 calc R . . C13 C -0.0218(3) 1.0596(4) 0.28588(17) 0.0239(7) Uani 1 1 d . . . H13 H -0.0684 1.1576 0.2986 0.029 Uiso 1 1 calc R . . C19 C 0.2849(3) 0.5137(4) 0.23617(16) 0.0215(7) Uani 1 1 d . . . H19A H 0.2908 0.5045 0.2930 0.026 Uiso 1 1 calc R . . H19B H 0.3795 0.5488 0.2173 0.026 Uiso 1 1 calc R . . C23 C 0.4800(3) -0.0222(5) 0.18778(19) 0.0306(8) Uani 1 1 d . . . H23A H 0.5390 0.0077 0.2327 0.046 Uiso 1 1 calc R . . H23B H 0.5417 -0.0395 0.1433 0.046 Uiso 1 1 calc R . . H23C H 0.4276 -0.1215 0.1989 0.046 Uiso 1 1 calc R . . C26 C 0.2192(3) 0.5967(4) 0.02335(16) 0.0169(6) Uani 1 1 d . . . C11 C 0.1582(3) 0.8596(4) 0.31739(16) 0.0220(7) Uani 1 1 d . . . H11 H 0.2307 0.8194 0.3512 0.026 Uiso 1 1 calc R . . C12 C 0.0881(3) 1.0018(4) 0.33386(17) 0.0250(7) Uani 1 1 d . . . H12 H 0.1151 1.0612 0.3785 0.030 Uiso 1 1 calc R . . C30 C 0.2114(3) 0.7595(4) -0.08879(15) 0.0198(6) Uani 1 1 d . . . C17 C 0.1734(3) 0.6330(4) 0.21364(16) 0.0210(7) Uani 1 1 d . . . C14 C -0.0645(3) 0.9764(4) 0.21970(16) 0.0221(7) Uani 1 1 d . . . H14 H -0.1419 1.0132 0.1882 0.027 Uiso 1 1 calc R . . C25 C 0.2258(3) 0.2350(4) 0.07019(16) 0.0204(6) Uani 1 1 d . . . C32 C 0.2719(3) 0.9226(5) -0.18497(18) 0.0295(8) Uani 1 1 d . . . H32A H 0.2431 1.0360 -0.1935 0.035 Uiso 1 1 calc R . . H32B H 0.2990 0.8756 -0.2351 0.035 Uiso 1 1 calc R . . N1 N -0.0019(2) 0.7374(3) 0.13835(13) 0.0193(5) Uani 1 1 d . . . H1A H -0.0630 0.7488 0.0997 0.023 Uiso 1 1 calc R . . N2 N 0.2162(2) 0.3640(3) 0.11621(13) 0.0176(5) Uani 1 1 d . . . N3 N 0.3794(2) 0.1054(3) 0.17068(14) 0.0230(6) Uani 1 1 d . . . O5 O 0.18701(18) 0.2354(3) 0.00195(11) 0.0218(5) Uani 1 1 d . . . O4 O 0.4309(2) 0.2427(3) 0.28065(11) 0.0261(5) Uani 1 1 d . . . O7 O 0.3908(2) 0.9152(3) -0.13176(12) 0.0281(5) Uani 1 1 d . . . O6 O 0.1558(2) 0.8338(3) -0.15297(12) 0.0285(5) 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 O3 0.0221(10) 0.0272(14) 0.0225(11) 0.0040(9) -0.0048(8) -0.0035(9) O1 0.0225(10) 0.0275(15) 0.0228(11) 0.0045(10) -0.0051(8) -0.0011(8) O2 0.0278(10) 0.0255(14) 0.0222(11) 0.0057(10) -0.0046(8) 0.0002(9) C4 0.0219(13) 0.0159(18) 0.0172(14) -0.0013(13) -0.0005(11) 0.0016(11) C9 0.0285(15) 0.022(2) 0.0247(16) 0.0020(14) -0.0039(12) 0.0007(12) C6 0.0218(14) 0.0198(19) 0.0223(15) 0.0002(13) 0.0031(11) -0.0045(11) C3 0.0200(13) 0.0153(19) 0.0221(15) -0.0009(13) 0.0025(11) -0.0002(11) C8 0.0216(13) 0.027(2) 0.0242(16) 0.0000(14) 0.0022(11) 0.0010(12) C2 0.0260(14) 0.018(2) 0.0172(14) 0.0020(13) -0.0003(11) 0.0021(11) C1 0.0201(13) 0.025(2) 0.0159(14) -0.0067(13) -0.0011(11) 0.0033(11) C7 0.0251(13) 0.0185(19) 0.0204(15) -0.0054(14) -0.0018(11) 0.0018(12) C5 0.0276(15) 0.022(2) 0.0152(14) 0.0000(13) 0.0019(11) 0.0025(12) C10 0.0282(15) 0.034(2) 0.0292(17) 0.0048(15) -0.0059(13) -0.0076(14) C18 0.0189(12) 0.0180(19) 0.0173(14) 0.0014(12) -0.0012(11) -0.0017(11) C22 0.0242(14) 0.024(2) 0.0174(14) 0.0071(14) -0.0004(11) -0.0016(12) C31 0.0184(12) 0.0205(19) 0.0207(14) -0.0021(13) -0.0007(11) -0.0003(11) C24 0.0241(14) 0.023(2) 0.0228(15) -0.0005(14) -0.0039(12) -0.0007(12) C20 0.0161(12) 0.026(2) 0.0186(14) -0.0008(13) -0.0033(10) 0.0013(11) C15 0.0194(12) 0.028(2) 0.0160(14) 0.0028(13) 0.0003(11) -0.0034(12) C16 0.0190(12) 0.0179(19) 0.0173(14) 0.0000(12) 0.0007(11) -0.0014(11) C28 0.0190(12) 0.0229(19) 0.0190(14) -0.0062(14) 0.0040(11) -0.0005(12) C29 0.0276(14) 0.0167(19) 0.0189(15) -0.0033(13) 0.0040(12) -0.0007(11) C27 0.0244(14) 0.022(2) 0.0141(14) -0.0058(13) -0.0003(11) 0.0068(12) C21 0.0213(13) 0.026(2) 0.0152(14) 0.0018(13) -0.0011(11) 0.0022(12) C13 0.0281(14) 0.020(2) 0.0235(16) -0.0029(13) 0.0077(12) 0.0000(12) C19 0.0218(13) 0.027(2) 0.0152(14) -0.0017(14) -0.0011(11) 0.0005(12) C23 0.0318(16) 0.032(2) 0.0273(17) -0.0009(15) -0.0048(13) 0.0061(14) C26 0.0228(13) 0.0120(18) 0.0160(14) -0.0027(12) 0.0014(11) 0.0053(11) C11 0.0197(13) 0.027(2) 0.0196(15) 0.0032(13) -0.0008(11) -0.0006(12) C12 0.0265(14) 0.028(2) 0.0209(15) -0.0083(14) 0.0003(12) -0.0032(13) C30 0.0256(14) 0.0202(19) 0.0136(13) 0.0004(13) -0.0010(11) 0.0062(12) C17 0.0195(13) 0.028(2) 0.0156(14) 0.0019(13) 0.0009(11) -0.0026(12) C14 0.0218(13) 0.027(2) 0.0180(15) 0.0046(13) 0.0012(11) 0.0026(12) C25 0.0156(12) 0.0232(19) 0.0224(15) -0.0010(14) -0.0033(11) -0.0024(11) C32 0.0312(16) 0.033(2) 0.0246(17) 0.0092(15) 0.0028(13) 0.0002(13) N1 0.0184(11) 0.0230(17) 0.0163(12) 0.0001(11) -0.0052(9) 0.0025(10) N2 0.0196(10) 0.0188(16) 0.0143(12) 0.0005(11) -0.0040(9) -0.0012(9) N3 0.0249(12) 0.0227(17) 0.0213(13) 0.0006(12) -0.0043(10) 0.0021(10) O5 0.0201(9) 0.0278(14) 0.0173(10) -0.0009(9) -0.0040(7) 0.0001(9) O4 0.0305(10) 0.0287(14) 0.0189(10) 0.0021(10) -0.0068(8) 0.0029(10) O7 0.0333(11) 0.0271(15) 0.0239(11) 0.0040(10) 0.0028(9) -0.0072(9) O6 0.0280(10) 0.0324(16) 0.0250(11) 0.0078(10) -0.0040(9) -0.0018(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O3 C7 1.338(4) . ? O3 C8 1.448(3) . ? O1 C1 1.356(3) . ? O1 H1 0.8400 . ? O2 C7 1.211(4) . ? C4 C3 1.384(4) . ? C4 C5 1.405(4) . ? C4 C7 1.488(4) . ? C9 C8 1.509(4) . ? C9 C10 1.530(4) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C6 C5 1.380(4) . ? C6 C1 1.390(4) . ? C6 H6 0.9500 . ? C3 C2 1.382(4) . ? C3 H3 0.9500 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C2 C1 1.395(4) . ? C2 H2 0.9500 . ? C5 H5 0.9500 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C18 C17 1.366(4) . ? C18 N1 1.374(4) . ? C18 C20 1.492(4) . ? C22 O4 1.234(3) . ? C22 N3 1.339(4) . ? C22 C21 1.531(4) . ? C31 C30 1.372(4) . ? C31 C26 1.400(4) . ? C31 H33 0.9500 . ? C24 N3 1.456(4) . ? C24 C25 1.504(4) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C20 N2 1.482(4) . ? C20 C26 1.532(4) . ? C20 H20 1.0000 . ? C15 C14 1.382(4) . ? C15 N1 1.384(4) . ? C15 C16 1.421(4) . ? C16 C11 1.399(4) . ? C16 C17 1.434(4) . ? C28 C29 1.370(4) . ? C28 C27 1.401(4) . ? C28 H28 0.9500 . ? C29 C30 1.376(4) . ? C29 O7 1.380(4) . ? C27 C26 1.388(4) . ? C27 H27 0.9500 . ? C21 N2 1.492(3) . ? C21 C19 1.524(4) . ? C21 H21 1.0000 . ? C13 C14 1.394(4) . ? C13 C12 1.397(4) . ? C13 H13 0.9500 . ? C19 C17 1.486(4) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C23 N3 1.444(4) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C11 C12 1.383(5) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C30 O6 1.369(3) . ? C14 H14 0.9500 . ? C25 O5 1.233(3) . ? C25 N2 1.340(4) . ? C32 O6 1.430(4) . ? C32 O7 1.434(4) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? N1 H1A 0.8800 . ? 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 C7 O3 C8 117.0(2) . . ? C1 O1 H1 109.5 . . ? C3 C4 C5 119.2(2) . . ? C3 C4 C7 122.3(3) . . ? C5 C4 C7 118.5(3) . . ? C8 C9 C10 110.1(3) . . ? C8 C9 H9A 109.6 . . ? C10 C9 H9A 109.6 . . ? C8 C9 H9B 109.6 . . ? C10 C9 H9B 109.6 . . ? H9A C9 H9B 108.1 . . ? C5 C6 C1 120.2(3) . . ? C5 C6 H6 119.9 . . ? C1 C6 H6 119.9 . . ? C2 C3 C4 120.8(3) . . ? C2 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? O3 C8 C9 111.9(2) . . ? O3 C8 H8A 109.2 . . ? C9 C8 H8A 109.2 . . ? O3 C8 H8B 109.2 . . ? C9 C8 H8B 109.2 . . ? H8A C8 H8B 107.9 . . ? C3 C2 C1 120.0(3) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? O1 C1 C6 117.7(3) . . ? O1 C1 C2 122.6(3) . . ? C6 C1 C2 119.7(2) . . ? O2 C7 O3 123.8(2) . . ? O2 C7 C4 124.7(3) . . ? O3 C7 C4 111.5(2) . . ? C6 C5 C4 120.2(3) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C17 C18 N1 110.6(3) . . ? C17 C18 C20 124.5(3) . . ? N1 C18 C20 124.1(2) . . ? O4 C22 N3 123.6(3) . . ? O4 C22 C21 118.7(3) . . ? N3 C22 C21 117.8(2) . . ? C30 C31 C26 117.5(3) . . ? C30 C31 H33 121.2 . . ? C26 C31 H33 121.2 . . ? N3 C24 C25 114.2(3) . . ? N3 C24 H24A 108.7 . . ? C25 C24 H24A 108.7 . . ? N3 C24 H24B 108.7 . . ? C25 C24 H24B 108.7 . . ? H24A C24 H24B 107.6 . . ? N2 C20 C18 109.7(2) . . ? N2 C20 C26 113.2(2) . . ? C18 C20 C26 107.2(3) . . ? N2 C20 H20 108.9 . . ? C18 C20 H20 108.9 . . ? C26 C20 H20 108.9 . . ? C14 C15 N1 130.3(3) . . ? C14 C15 C16 122.3(3) . . ? N1 C15 C16 107.4(3) . . ? C11 C16 C15 118.9(3) . . ? C11 C16 C17 134.2(3) . . ? C15 C16 C17 106.9(2) . . ? C29 C28 C27 117.5(3) . . ? C29 C28 H28 121.2 . . ? C27 C28 H28 121.2 . . ? C28 C29 C30 121.3(3) . . ? C28 C29 O7 129.1(3) . . ? C30 C29 O7 109.5(2) . . ? C26 C27 C28 121.1(3) . . ? C26 C27 H27 119.4 . . ? C28 C27 H27 119.4 . . ? N2 C21 C19 112.0(2) . . ? N2 C21 C22 112.3(2) . . ? C19 C21 C22 109.9(2) . . ? N2 C21 H21 107.5 . . ? C19 C21 H21 107.5 . . ? C22 C21 H21 107.5 . . ? C14 C13 C12 121.3(3) . . ? C14 C13 H13 119.4 . . ? C12 C13 H13 119.4 . . ? C17 C19 C21 108.5(2) . . ? C17 C19 H19A 110.0 . . ? C21 C19 H19A 110.0 . . ? C17 C19 H19B 110.0 . . ? C21 C19 H19B 110.0 . . ? H19A C19 H19B 108.4 . . ? N3 C23 H23A 109.5 . . ? N3 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? N3 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C27 C26 C31 120.3(3) . . ? C27 C26 C20 122.0(2) . . ? C31 C26 C20 117.2(2) . . ? C12 C11 C16 119.0(3) . . ? C12 C11 H11 120.5 . . ? C16 C11 H11 120.5 . . ? C11 C12 C13 121.1(3) . . ? C11 C12 H12 119.5 . . ? C13 C12 H12 119.5 . . ? O6 C30 C31 127.2(2) . . ? O6 C30 C29 110.6(3) . . ? C31 C30 C29 122.1(3) . . ? C18 C17 C16 106.6(3) . . ? C18 C17 C19 120.7(3) . . ? C16 C17 C19 132.7(3) . . ? C15 C14 C13 117.4(3) . . ? C15 C14 H14 121.3 . . ? C13 C14 H14 121.3 . . ? O5 C25 N2 123.3(3) . . ? O5 C25 C24 118.8(3) . . ? N2 C25 C24 118.0(2) . . ? O6 C32 O7 108.1(2) . . ? O6 C32 H32A 110.1 . . ? O7 C32 H32A 110.1 . . ? O6 C32 H32B 110.1 . . ? O7 C32 H32B 110.1 . . ? H32A C32 H32B 108.4 . . ? C18 N1 C15 108.5(2) . . ? C18 N1 H1A 125.8 . . ? C15 N1 H1A 125.8 . . ? C25 N2 C20 115.3(2) . . ? C25 N2 C21 121.2(3) . . ? C20 N2 C21 121.0(2) . . ? C22 N3 C23 120.8(2) . . ? C22 N3 C24 121.8(2) . . ? C23 N3 C24 116.7(3) . . ? C29 O7 C32 105.5(2) . . ? C30 O6 C32 105.6(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 C5 C4 C3 C2 -0.5(4) . . . . ? C7 C4 C3 C2 177.3(3) . . . . ? C7 O3 C8 C9 -84.6(3) . . . . ? C10 C9 C8 O3 -175.6(3) . . . . ? C4 C3 C2 C1 0.8(5) . . . . ? C5 C6 C1 O1 179.3(3) . . . . ? C5 C6 C1 C2 -0.5(5) . . . . ? C3 C2 C1 O1 179.9(3) . . . . ? C3 C2 C1 C6 -0.3(4) . . . . ? C8 O3 C7 O2 2.2(4) . . . . ? C8 O3 C7 C4 -175.3(2) . . . . ? C3 C4 C7 O2 179.2(3) . . . . ? C5 C4 C7 O2 -3.0(5) . . . . ? C3 C4 C7 O3 -3.3(4) . . . . ? C5 C4 C7 O3 174.5(3) . . . . ? C1 C6 C5 C4 0.8(5) . . . . ? C3 C4 C5 C6 -0.3(5) . . . . ? C7 C4 C5 C6 -178.2(3) . . . . ? C17 C18 C20 N2 26.0(4) . . . . ? N1 C18 C20 N2 -165.5(2) . . . . ? C17 C18 C20 C26 -97.3(3) . . . . ? N1 C18 C20 C26 71.2(3) . . . . ? C14 C15 C16 C11 -1.8(4) . . . . ? N1 C15 C16 C11 177.7(3) . . . . ? C14 C15 C16 C17 179.9(3) . . . . ? N1 C15 C16 C17 -0.5(3) . . . . ? C27 C28 C29 C30 -0.9(4) . . . . ? C27 C28 C29 O7 177.9(3) . . . . ? C29 C28 C27 C26 0.4(4) . . . . ? O4 C22 C21 N2 154.2(3) . . . . ? N3 C22 C21 N2 -26.2(4) . . . . ? O4 C22 C21 C19 28.8(4) . . . . ? N3 C22 C21 C19 -151.6(3) . . . . ? N2 C21 C19 C17 52.3(3) . . . . ? C22 C21 C19 C17 177.8(2) . . . . ? C28 C27 C26 C31 0.7(5) . . . . ? C28 C27 C26 C20 -170.4(3) . . . . ? C30 C31 C26 C27 -1.4(4) . . . . ? C30 C31 C26 C20 170.1(3) . . . . ? N2 C20 C26 C27 -47.0(4) . . . . ? C18 C20 C26 C27 74.1(3) . . . . ? N2 C20 C26 C31 141.6(3) . . . . ? C18 C20 C26 C31 -97.3(3) . . . . ? C15 C16 C11 C12 -1.1(4) . . . . ? C17 C16 C11 C12 176.6(3) . . . . ? C16 C11 C12 C13 2.1(4) . . . . ? C14 C13 C12 C11 -0.1(5) . . . . ? C26 C31 C30 O6 -177.7(3) . . . . ? C26 C31 C30 C29 1.0(5) . . . . ? C28 C29 C30 O6 179.1(3) . . . . ? O7 C29 C30 O6 0.1(3) . . . . ? C28 C29 C30 C31 0.1(5) . . . . ? O7 C29 C30 C31 -178.9(3) . . . . ? N1 C18 C17 C16 -1.5(3) . . . . ? C20 C18 C17 C16 168.4(3) . . . . ? N1 C18 C17 C19 178.3(3) . . . . ? C20 C18 C17 C19 -11.9(4) . . . . ? C11 C16 C17 C18 -176.6(3) . . . . ? C15 C16 C17 C18 1.2(3) . . . . ? C11 C16 C17 C19 3.6(6) . . . . ? C15 C16 C17 C19 -178.5(3) . . . . ? C21 C19 C17 C18 -28.6(4) . . . . ? C21 C19 C17 C16 151.1(3) . . . . ? N1 C15 C14 C13 -175.8(3) . . . . ? C16 C15 C14 C13 3.7(4) . . . . ? C12 C13 C14 C15 -2.7(4) . . . . ? N3 C24 C25 O5 155.5(2) . . . . ? N3 C24 C25 N2 -25.6(4) . . . . ? C17 C18 N1 C15 1.2(3) . . . . ? C20 C18 N1 C15 -168.7(3) . . . . ? C14 C15 N1 C18 179.1(3) . . . . ? C16 C15 N1 C18 -0.4(3) . . . . ? O5 C25 N2 C20 9.0(4) . . . . ? C24 C25 N2 C20 -169.8(2) . . . . ? O5 C25 N2 C21 171.2(2) . . . . ? C24 C25 N2 C21 -7.6(4) . . . . ? C18 C20 N2 C25 164.4(2) . . . . ? C26 C20 N2 C25 -75.9(3) . . . . ? C18 C20 N2 C21 2.2(3) . . . . ? C26 C20 N2 C21 121.8(3) . . . . ? C19 C21 N2 C25 157.8(2) . . . . ? C22 C21 N2 C25 33.6(3) . . . . ? C19 C21 N2 C20 -41.0(3) . . . . ? C22 C21 N2 C20 -165.3(2) . . . . ? O4 C22 N3 C23 3.7(4) . . . . ? C21 C22 N3 C23 -175.9(3) . . . . ? O4 C22 N3 C24 173.3(3) . . . . ? C21 C22 N3 C24 -6.3(4) . . . . ? C25 C24 N3 C22 33.1(4) . . . . ? C25 C24 N3 C23 -156.9(3) . . . . ? C28 C29 O7 C32 176.2(3) . . . . ? C30 C29 O7 C32 -4.9(3) . . . . ? O6 C32 O7 C29 7.8(3) . . . . ? C31 C30 O6 C32 -176.3(3) . . . . ? C29 C30 O6 C32 4.8(3) . . . . ? O7 C32 O6 C30 -7.8(4) . . . . ? 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 O1 H1 O4 0.84 1.91 2.748(3) 175.4 . N1 H1A O5 0.88 2.10 2.965(3) 168.3 2 _diffrn_measured_fraction_theta_max 0.942 _diffrn_reflns_theta_full 65.81 _diffrn_measured_fraction_theta_full 0.942 _refine_diff_density_max 0.171 _refine_diff_density_min -0.221 _refine_diff_density_rms 0.045 #===END ########################################################## data_TDF_HCA_3 _database_code_depnum_ccdc_archive 'CCDC 855600' #TrackingRef '- TDF cocrystals cif file 20111123.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'tadalafil hydrocinnamic acid ' _chemical_melting_point 366.08 _chemical_formula_moiety 'C22 H19 N3 O4, C9 H10 O2' _chemical_formula_sum 'C31 H29 N3 O6' _chemical_formula_weight 539.57 _chemical_absolute_configuration syn loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.5476(12) _cell_length_b 8.1881(10) _cell_length_c 16.673(2) _cell_angle_alpha 90.00 _cell_angle_beta 96.305(9) _cell_angle_gamma 90.00 _cell_volume 1295.5(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1668 _cell_measurement_theta_min 2.67 _cell_measurement_theta_max 57.2 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.383 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.795 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6920 _exptl_absorpt_correction_T_max 0.9921 _exptl_absorpt_process_details 'SADABS; (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART APEXII CCD' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8513 _diffrn_reflns_av_R_equivalents 0.0439 _diffrn_reflns_av_sigmaI/netI 0.0575 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.67 _diffrn_reflns_theta_max 65.97 _reflns_number_total 3654 _reflns_number_gt 3098 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2010)' _computing_cell_refinement 'APEX2 (Bruker, 2010); SAINT (Bruker, 2009)' _computing_data_reduction 'SAINT (Bruker, 2009);XPREP(Sheldrick,2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material 'APEX2 (Bruker, 2010)' _publ_section_references ; Bruker AXS. (2010). APEX2 Bruker AXS, Inc. Madison, Wisconsin, USA. Bruker AXS. (2009). SAINT Bruker AXS, Inc. Madison, Wisconsin, USA. Sheldrick, G. M. (2008). SADABS. University of G\"ottingen, Germany. Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122. ; _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^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.5(2) _refine_ls_number_reflns 3654 _refine_ls_number_parameters 363 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0514 _refine_ls_R_factor_gt 0.0420 _refine_ls_wR_factor_ref 0.1007 _refine_ls_wR_factor_gt 0.0957 _refine_ls_goodness_of_fit_ref 0.980 _refine_ls_restrained_S_all 0.980 _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 C1 C 0.9145(3) 0.5018(4) 0.00599(19) 0.0283(7) Uani 1 1 d . . . C2 C 0.8432(3) 0.5791(4) 0.07261(18) 0.0310(8) Uani 1 1 d . . . H2A H 0.7493 0.6202 0.0504 0.037 Uiso 1 1 calc R . . H2B H 0.8998 0.6734 0.0948 0.037 Uiso 1 1 calc R . . C3 C 0.8260(3) 0.4566(4) 0.14060(18) 0.0302(7) Uani 1 1 d . . . H3A H 0.9194 0.4108 0.1604 0.036 Uiso 1 1 calc R . . H3B H 0.7893 0.5145 0.1861 0.036 Uiso 1 1 calc R . . C4 C 0.7265(3) 0.3180(4) 0.11291(17) 0.0250(7) Uani 1 1 d . . . C5 C 0.5828(3) 0.3370(4) 0.11736(18) 0.0296(7) Uani 1 1 d . . . H5 H 0.5484 0.4350 0.1387 0.036 Uiso 1 1 calc R . . C6 C 0.4892(4) 0.2135(4) 0.09079(18) 0.0329(8) Uani 1 1 d . . . H6 H 0.3913 0.2270 0.0945 0.040 Uiso 1 1 calc R . . C7 C 0.5378(4) 0.0714(4) 0.05906(17) 0.0343(8) Uani 1 1 d . . . H7 H 0.4735 -0.0122 0.0403 0.041 Uiso 1 1 calc R . . C8 C 0.6804(4) 0.0510(4) 0.05473(18) 0.0345(8) Uani 1 1 d . . . H8 H 0.7144 -0.0468 0.0331 0.041 Uiso 1 1 calc R . . C9 C 0.7743(3) 0.1741(4) 0.08217(18) 0.0294(7) Uani 1 1 d . . . H9 H 0.8724 0.1590 0.0797 0.035 Uiso 1 1 calc R . . C10 C 1.0050(4) 0.1777(4) 0.6947(2) 0.0362(8) Uani 1 1 d . . . H10A H 1.0733 0.2122 0.7397 0.054 Uiso 1 1 calc R . . H10B H 1.0541 0.1554 0.6473 0.054 Uiso 1 1 calc R . . H10C H 0.9568 0.0785 0.7099 0.054 Uiso 1 1 calc R . . C11 C 0.8004(3) 0.2828(4) 0.60513(18) 0.0269(7) Uani 1 1 d . . . H11A H 0.7243 0.2102 0.6199 0.032 Uiso 1 1 calc R . . H11B H 0.8480 0.2266 0.5631 0.032 Uiso 1 1 calc R . . C12 C 0.7353(3) 0.4386(4) 0.57021(16) 0.0238(7) Uani 1 1 d . . . C13 C 0.7730(3) 0.5555(4) 0.70798(16) 0.0233(7) Uani 1 1 d . . . H13 H 0.6871 0.5222 0.7332 0.028 Uiso 1 1 calc R . . C14 C 0.8863(3) 0.4256(4) 0.72963(17) 0.0266(7) Uani 1 1 d . . . C15 C 0.6493(3) 0.7110(4) 0.58404(17) 0.0231(7) Uani 1 1 d . . . H15 H 0.5559 0.6711 0.5584 0.028 Uiso 1 1 calc R . . C16 C 0.8227(3) 0.7194(4) 0.74477(17) 0.0251(7) Uani 1 1 d . . . H16A H 0.8377 0.7107 0.8043 0.030 Uiso 1 1 calc R . . H16B H 0.9129 0.7515 0.7251 0.030 Uiso 1 1 calc R . . C17 C 0.7112(3) 0.8449(4) 0.72014(17) 0.0225(7) Uani 1 1 d . . . C18 C 0.6258(3) 0.8279(4) 0.65015(16) 0.0212(7) Uani 1 1 d . . . C19 C 0.7223(3) 0.8044(4) 0.52140(16) 0.0219(7) Uani 1 1 d . . . C20 C 0.8647(3) 0.8453(4) 0.53463(17) 0.0240(7) Uani 1 1 d . . . H20 H 0.9208 0.8004 0.5799 0.029 Uiso 1 1 calc R . . C21 C 0.9275(3) 0.9514(4) 0.48257(17) 0.0268(7) Uani 1 1 d . . . H21 H 1.0248 0.9784 0.4914 0.032 Uiso 1 1 calc R . . C22 C 0.8416(3) 1.0143(4) 0.41844(17) 0.0259(7) Uani 1 1 d . . . C23 C 0.7011(3) 0.9734(4) 0.40480(17) 0.0245(7) Uani 1 1 d . . . C24 C 0.6383(3) 0.8685(4) 0.45454(17) 0.0236(7) Uani 1 1 d . . . H24 H 0.5415 0.8406 0.4440 0.028 Uiso 1 1 calc R . . C25 C 0.7489(4) 1.1385(5) 0.3046(2) 0.0434(10) Uani 1 1 d . . . H25A H 0.7240 1.2556 0.2986 0.052 Uiso 1 1 calc R . . H25B H 0.7633 1.0945 0.2509 0.052 Uiso 1 1 calc R . . C26 C 0.6640(3) 0.9877(4) 0.75997(17) 0.0234(7) Uani 1 1 d . . . C27 C 0.7098(3) 1.0697(4) 0.83198(17) 0.0259(7) Uani 1 1 d . . . H27 H 0.7890 1.0317 0.8663 0.031 Uiso 1 1 calc R . . C28 C 0.6372(4) 1.2066(4) 0.85173(18) 0.0320(8) Uani 1 1 d . . . H28 H 0.6674 1.2633 0.9003 0.038 Uiso 1 1 calc R . . C29 C 0.5192(4) 1.2645(4) 0.80172(18) 0.0333(8) Uani 1 1 d . . . H29 H 0.4714 1.3593 0.8171 0.040 Uiso 1 1 calc R . . C30 C 0.4719(3) 1.1854(4) 0.73039(17) 0.0282(7) Uani 1 1 d . . . H30 H 0.3912 1.2230 0.6971 0.034 Uiso 1 1 calc R . . C31 C 0.5466(3) 1.0490(4) 0.70932(17) 0.0246(7) Uani 1 1 d . . . N1 N 0.9016(3) 0.3073(3) 0.67580(14) 0.0258(6) Uani 1 1 d . . . N2 N 0.7327(2) 0.5686(3) 0.61915(13) 0.0220(6) Uani 1 1 d . . . N3 N 0.5258(2) 0.9491(3) 0.64187(14) 0.0252(6) Uani 1 1 d . . . H3 H 0.4601 0.9612 0.6010 0.030 Uiso 1 1 calc R . . O1 O 0.8495(2) 0.5350(3) -0.06731(12) 0.0345(6) Uani 1 1 d . . . H1 H 0.8896 0.4847 -0.1023 0.052 Uiso 1 1 calc R . . O2 O 1.0192(2) 0.4190(3) 0.01698(13) 0.0367(6) Uani 1 1 d . . . O3 O 0.8756(2) 1.1200(3) 0.35912(12) 0.0351(6) Uani 1 1 d . . . O4 O 0.6386(2) 1.0518(3) 0.33686(12) 0.0341(5) Uani 1 1 d . . . O5 O 0.6858(2) 0.4401(3) 0.49836(11) 0.0271(5) Uani 1 1 d . . . O6 O 0.9596(2) 0.4335(3) 0.79559(11) 0.0325(5) 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 C1 0.0296(17) 0.0313(19) 0.0241(15) 0.0048(13) 0.0030(13) -0.0089(15) C2 0.0310(17) 0.031(2) 0.0311(17) -0.0001(15) 0.0056(14) -0.0065(16) C3 0.0309(17) 0.038(2) 0.0213(15) -0.0019(15) 0.0026(13) -0.0027(16) C4 0.0257(16) 0.0324(19) 0.0170(14) 0.0046(14) 0.0031(12) -0.0001(15) C5 0.0310(17) 0.033(2) 0.0258(16) -0.0002(15) 0.0057(14) 0.0004(16) C6 0.0294(18) 0.043(2) 0.0272(17) 0.0017(16) 0.0049(14) -0.0012(17) C7 0.045(2) 0.035(2) 0.0222(16) 0.0042(15) 0.0027(15) -0.0138(18) C8 0.050(2) 0.0258(19) 0.0289(17) 0.0010(16) 0.0106(15) 0.0014(18) C9 0.0291(17) 0.0321(19) 0.0282(16) 0.0036(15) 0.0090(14) 0.0058(16) C10 0.040(2) 0.033(2) 0.0344(18) 0.0000(16) -0.0031(15) 0.0096(17) C11 0.0276(17) 0.0297(19) 0.0234(15) -0.0003(14) 0.0031(13) 0.0016(15) C12 0.0179(14) 0.0339(19) 0.0203(15) 0.0022(14) 0.0057(12) -0.0021(15) C13 0.0185(14) 0.0339(19) 0.0175(14) 0.0018(14) 0.0020(11) 0.0012(15) C14 0.0305(17) 0.0312(19) 0.0185(15) 0.0061(14) 0.0042(13) 0.0030(16) C15 0.0224(15) 0.0269(18) 0.0196(14) 0.0020(13) 0.0001(12) 0.0023(14) C16 0.0257(16) 0.0303(19) 0.0194(15) -0.0018(13) 0.0031(13) 0.0002(14) C17 0.0217(15) 0.0299(19) 0.0164(14) 0.0000(13) 0.0045(12) 0.0021(14) C18 0.0217(15) 0.0238(18) 0.0189(14) 0.0002(13) 0.0065(12) 0.0017(14) C19 0.0248(15) 0.0243(17) 0.0170(14) -0.0032(13) 0.0042(12) 0.0016(14) C20 0.0247(16) 0.0282(19) 0.0193(14) -0.0016(13) 0.0028(12) 0.0061(14) C21 0.0222(15) 0.0334(19) 0.0256(15) -0.0047(15) 0.0068(13) -0.0010(15) C22 0.0334(17) 0.0243(18) 0.0212(15) -0.0006(13) 0.0084(13) -0.0037(15) C23 0.0289(16) 0.0255(18) 0.0189(14) -0.0008(13) 0.0021(13) -0.0008(14) C24 0.0217(15) 0.0284(18) 0.0206(15) -0.0027(13) 0.0016(13) -0.0003(13) C25 0.049(2) 0.051(3) 0.0307(19) 0.0204(17) 0.0032(16) -0.0011(19) C26 0.0222(15) 0.0293(19) 0.0200(14) 0.0033(13) 0.0075(12) -0.0024(13) C27 0.0273(16) 0.0291(18) 0.0217(15) 0.0001(14) 0.0039(13) -0.0046(15) C28 0.043(2) 0.0299(19) 0.0237(16) -0.0054(15) 0.0056(14) -0.0051(17) C29 0.044(2) 0.0281(19) 0.0280(17) -0.0012(15) 0.0069(16) 0.0059(17) C30 0.0329(17) 0.0289(19) 0.0235(15) 0.0037(15) 0.0069(13) 0.0064(16) C31 0.0277(15) 0.0281(18) 0.0189(14) 0.0017(14) 0.0060(12) -0.0043(15) N1 0.0289(14) 0.0290(16) 0.0192(12) 0.0036(12) 0.0011(11) 0.0056(13) N2 0.0216(12) 0.0271(14) 0.0172(12) 0.0013(11) 0.0015(10) 0.0018(12) N3 0.0251(13) 0.0307(15) 0.0193(12) 0.0012(12) -0.0002(10) 0.0060(13) O1 0.0383(13) 0.0417(15) 0.0234(11) -0.0005(11) 0.0024(10) 0.0042(12) O2 0.0310(13) 0.0469(15) 0.0330(13) 0.0063(11) 0.0064(10) 0.0077(12) O3 0.0395(13) 0.0405(15) 0.0258(12) 0.0066(10) 0.0064(10) -0.0080(11) O4 0.0360(12) 0.0397(14) 0.0252(11) 0.0120(11) -0.0030(10) -0.0061(12) O5 0.0273(11) 0.0331(13) 0.0205(11) -0.0022(10) 0.0003(9) 0.0014(11) O6 0.0357(12) 0.0381(14) 0.0219(11) 0.0014(10) -0.0046(9) 0.0114(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 C1 O2 1.205(4) . ? C1 O1 1.336(4) . ? C1 C2 1.505(5) . ? C2 C3 1.536(5) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.519(5) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C9 1.382(5) . ? C4 C5 1.391(4) . ? C5 C6 1.389(5) . ? C5 H5 0.9500 . ? C6 C7 1.380(5) . ? C6 H6 0.9500 . ? C7 C8 1.381(5) . ? C7 H7 0.9500 . ? C8 C9 1.392(5) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 N1 1.460(4) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 N1 1.453(4) . ? C11 C12 1.507(4) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 O5 1.239(3) . ? C12 N2 1.343(4) . ? C13 N2 1.493(3) . ? C13 C16 1.529(4) . ? C13 C14 1.532(4) . ? C13 H13 1.0000 . ? C14 O6 1.239(3) . ? C14 N1 1.339(4) . ? C15 N2 1.494(4) . ? C15 C18 1.496(4) . ? C15 C19 1.524(4) . ? C15 H15 1.0000 . ? C16 C17 1.504(4) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.355(4) . ? C17 C26 1.441(4) . ? C18 N3 1.373(4) . ? C19 C20 1.394(4) . ? C19 C24 1.402(4) . ? C20 C21 1.408(4) . ? C20 H20 0.9500 . ? C21 C22 1.374(4) . ? C21 H21 0.9500 . ? C22 C23 1.377(4) . ? C22 O3 1.379(4) . ? C23 C24 1.376(4) . ? C23 O4 1.380(3) . ? C24 H24 0.9500 . ? C25 O4 1.424(4) . ? C25 O3 1.439(4) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 C27 1.403(4) . ? C26 C31 1.419(4) . ? C27 C28 1.376(5) . ? C27 H27 0.9500 . ? C28 C29 1.408(4) . ? C28 H28 0.9500 . ? C29 C30 1.386(4) . ? C29 H29 0.9500 . ? C30 C31 1.391(5) . ? C30 H30 0.9500 . ? C31 N3 1.387(4) . ? N3 H3 0.8800 . ? O1 H1 0.8400 . ? 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 O2 C1 O1 123.2(3) . . ? O2 C1 C2 124.0(3) . . ? O1 C1 C2 112.8(3) . . ? C1 C2 C3 111.3(3) . . ? C1 C2 H2A 109.4 . . ? C3 C2 H2A 109.4 . . ? C1 C2 H2B 109.4 . . ? C3 C2 H2B 109.4 . . ? H2A C2 H2B 108.0 . . ? C4 C3 C2 112.2(2) . . ? C4 C3 H3A 109.2 . . ? C2 C3 H3A 109.2 . . ? C4 C3 H3B 109.2 . . ? C2 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? C9 C4 C5 118.9(3) . . ? C9 C4 C3 121.9(3) . . ? C5 C4 C3 119.2(3) . . ? C6 C5 C4 120.3(3) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C7 C6 C5 120.3(3) . . ? C7 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? C6 C7 C8 119.8(3) . . ? C6 C7 H7 120.1 . . ? C8 C7 H7 120.1 . . ? C7 C8 C9 119.9(3) . . ? C7 C8 H8 120.1 . . ? C9 C8 H8 120.1 . . ? C4 C9 C8 120.8(3) . . ? C4 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? N1 C10 H10A 109.5 . . ? N1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N1 C11 C12 113.9(3) . . ? N1 C11 H11A 108.8 . . ? C12 C11 H11A 108.8 . . ? N1 C11 H11B 108.8 . . ? C12 C11 H11B 108.8 . . ? H11A C11 H11B 107.7 . . ? O5 C12 N2 123.3(3) . . ? O5 C12 C11 118.6(3) . . ? N2 C12 C11 118.1(2) . . ? N2 C13 C16 111.7(3) . . ? N2 C13 C14 112.5(2) . . ? C16 C13 C14 109.6(2) . . ? N2 C13 H13 107.6 . . ? C16 C13 H13 107.6 . . ? C14 C13 H13 107.6 . . ? O6 C14 N1 122.7(3) . . ? O6 C14 C13 119.2(3) . . ? N1 C14 C13 118.0(2) . . ? N2 C15 C18 109.1(2) . . ? N2 C15 C19 113.3(2) . . ? C18 C15 C19 107.5(2) . . ? N2 C15 H15 109.0 . . ? C18 C15 H15 109.0 . . ? C19 C15 H15 109.0 . . ? C17 C16 C13 108.1(2) . . ? C17 C16 H16A 110.1 . . ? C13 C16 H16A 110.1 . . ? C17 C16 H16B 110.1 . . ? C13 C16 H16B 110.1 . . ? H16A C16 H16B 108.4 . . ? C18 C17 C26 106.9(3) . . ? C18 C17 C16 120.4(3) . . ? C26 C17 C16 132.5(3) . . ? C17 C18 N3 111.0(3) . . ? C17 C18 C15 125.1(3) . . ? N3 C18 C15 123.2(2) . . ? C20 C19 C24 119.9(3) . . ? C20 C19 C15 121.6(3) . . ? C24 C19 C15 117.9(3) . . ? C19 C20 C21 121.6(3) . . ? C19 C20 H20 119.2 . . ? C21 C20 H20 119.2 . . ? C22 C21 C20 116.9(3) . . ? C22 C21 H21 121.5 . . ? C20 C21 H21 121.5 . . ? C21 C22 C23 121.6(3) . . ? C21 C22 O3 128.7(3) . . ? C23 C22 O3 109.6(3) . . ? C24 C23 C22 122.2(3) . . ? C24 C23 O4 127.4(3) . . ? C22 C23 O4 110.4(3) . . ? C23 C24 C19 117.6(3) . . ? C23 C24 H24 121.2 . . ? C19 C24 H24 121.2 . . ? O4 C25 O3 108.3(2) . . ? O4 C25 H25A 110.0 . . ? O3 C25 H25A 110.0 . . ? O4 C25 H25B 110.0 . . ? O3 C25 H25B 110.0 . . ? H25A C25 H25B 108.4 . . ? C27 C26 C31 119.4(3) . . ? C27 C26 C17 134.4(3) . . ? C31 C26 C17 106.2(3) . . ? C28 C27 C26 118.5(3) . . ? C28 C27 H27 120.8 . . ? C26 C27 H27 120.8 . . ? C27 C28 C29 121.6(3) . . ? C27 C28 H28 119.2 . . ? C29 C28 H28 119.2 . . ? C30 C29 C28 121.0(3) . . ? C30 C29 H29 119.5 . . ? C28 C29 H29 119.5 . . ? C29 C30 C31 117.6(3) . . ? C29 C30 H30 121.2 . . ? C31 C30 H30 121.2 . . ? N3 C31 C30 130.3(3) . . ? N3 C31 C26 107.9(3) . . ? C30 C31 C26 121.8(3) . . ? C14 N1 C11 122.1(3) . . ? C14 N1 C10 120.1(2) . . ? C11 N1 C10 116.6(2) . . ? C12 N2 C13 121.7(2) . . ? C12 N2 C15 115.2(2) . . ? C13 N2 C15 120.9(2) . . ? C18 N3 C31 108.0(2) . . ? C18 N3 H3 126.0 . . ? C31 N3 H3 126.0 . . ? C1 O1 H1 109.5 . . ? C22 O3 C25 105.7(2) . . ? C23 O4 C25 105.7(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 O2 C1 C2 C3 -46.8(4) . . . . ? O1 C1 C2 C3 133.4(3) . . . . ? C1 C2 C3 C4 -65.5(3) . . . . ? C2 C3 C4 C9 91.2(3) . . . . ? C2 C3 C4 C5 -87.8(4) . . . . ? C9 C4 C5 C6 -0.4(5) . . . . ? C3 C4 C5 C6 178.6(3) . . . . ? C4 C5 C6 C7 -0.6(5) . . . . ? C5 C6 C7 C8 0.9(5) . . . . ? C6 C7 C8 C9 -0.2(5) . . . . ? C5 C4 C9 C8 1.1(4) . . . . ? C3 C4 C9 C8 -177.9(3) . . . . ? C7 C8 C9 C4 -0.8(5) . . . . ? N1 C11 C12 O5 156.8(3) . . . . ? N1 C11 C12 N2 -23.9(4) . . . . ? N2 C13 C14 O6 158.3(3) . . . . ? C16 C13 C14 O6 33.5(4) . . . . ? N2 C13 C14 N1 -21.8(4) . . . . ? C16 C13 C14 N1 -146.6(3) . . . . ? N2 C13 C16 C17 52.9(3) . . . . ? C14 C13 C16 C17 178.2(2) . . . . ? C13 C16 C17 C18 -28.1(4) . . . . ? C13 C16 C17 C26 147.1(3) . . . . ? C26 C17 C18 N3 -0.4(3) . . . . ? C16 C17 C18 N3 175.9(3) . . . . ? C26 C17 C18 C15 170.4(3) . . . . ? C16 C17 C18 C15 -13.3(5) . . . . ? N2 C15 C18 C17 26.7(4) . . . . ? C19 C15 C18 C17 -96.5(3) . . . . ? N2 C15 C18 N3 -163.6(3) . . . . ? C19 C15 C18 N3 73.2(3) . . . . ? N2 C15 C19 C20 -45.3(4) . . . . ? C18 C15 C19 C20 75.3(3) . . . . ? N2 C15 C19 C24 143.5(3) . . . . ? C18 C15 C19 C24 -95.9(3) . . . . ? C24 C19 C20 C21 0.5(5) . . . . ? C15 C19 C20 C21 -170.6(3) . . . . ? C19 C20 C21 C22 0.6(5) . . . . ? C20 C21 C22 C23 -1.1(4) . . . . ? C20 C21 C22 O3 179.9(3) . . . . ? C21 C22 C23 C24 0.4(5) . . . . ? O3 C22 C23 C24 179.6(3) . . . . ? C21 C22 C23 O4 -179.8(3) . . . . ? O3 C22 C23 O4 -0.6(3) . . . . ? C22 C23 C24 C19 0.7(4) . . . . ? O4 C23 C24 C19 -179.1(3) . . . . ? C20 C19 C24 C23 -1.1(4) . . . . ? C15 C19 C24 C23 170.3(3) . . . . ? C18 C17 C26 C27 -178.4(3) . . . . ? C16 C17 C26 C27 5.9(6) . . . . ? C18 C17 C26 C31 0.8(3) . . . . ? C16 C17 C26 C31 -174.9(3) . . . . ? C31 C26 C27 C28 0.9(4) . . . . ? C17 C26 C27 C28 -179.9(3) . . . . ? C26 C27 C28 C29 0.2(5) . . . . ? C27 C28 C29 C30 -0.1(5) . . . . ? C28 C29 C30 C31 -1.2(5) . . . . ? C29 C30 C31 N3 -178.6(3) . . . . ? C29 C30 C31 C26 2.4(4) . . . . ? C27 C26 C31 N3 178.5(3) . . . . ? C17 C26 C31 N3 -0.9(3) . . . . ? C27 C26 C31 C30 -2.3(4) . . . . ? C17 C26 C31 C30 178.3(3) . . . . ? O6 C14 N1 C11 169.3(3) . . . . ? C13 C14 N1 C11 -10.6(4) . . . . ? O6 C14 N1 C10 1.9(5) . . . . ? C13 C14 N1 C10 -178.0(3) . . . . ? C12 C11 N1 C14 34.4(4) . . . . ? C12 C11 N1 C10 -157.9(3) . . . . ? O5 C12 N2 C13 170.4(3) . . . . ? C11 C12 N2 C13 -8.8(4) . . . . ? O5 C12 N2 C15 7.4(4) . . . . ? C11 C12 N2 C15 -171.8(2) . . . . ? C16 C13 N2 C12 155.5(3) . . . . ? C14 C13 N2 C12 31.8(4) . . . . ? C16 C13 N2 C15 -42.4(3) . . . . ? C14 C13 N2 C15 -166.1(2) . . . . ? C18 C15 N2 C12 166.2(2) . . . . ? C19 C15 N2 C12 -74.2(3) . . . . ? C18 C15 N2 C13 3.0(4) . . . . ? C19 C15 N2 C13 122.7(3) . . . . ? C17 C18 N3 C31 -0.1(3) . . . . ? C15 C18 N3 C31 -171.2(3) . . . . ? C30 C31 N3 C18 -178.5(3) . . . . ? C26 C31 N3 C18 0.6(3) . . . . ? C21 C22 O3 C25 176.8(3) . . . . ? C23 C22 O3 C25 -2.4(3) . . . . ? O4 C25 O3 C22 4.4(4) . . . . ? C24 C23 O4 C25 -176.9(3) . . . . ? C22 C23 O4 C25 3.3(3) . . . . ? O3 C25 O4 C23 -4.7(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H3 O5 0.88 2.05 2.918(3) 168.3 2_656 O1 H1 O6 0.84 1.94 2.748(3) 160.3 1_554 _diffrn_measured_fraction_theta_max 0.964 _diffrn_reflns_theta_full 65.97 _diffrn_measured_fraction_theta_full 0.964 _refine_diff_density_max 0.159 _refine_diff_density_min -0.196 _refine_diff_density_rms 0.045 #===END