# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Arijit Mukherjee' _publ_contact_author_email arijiit2007@gmail.com loop_ _publ_author_name 'Gautam R. Desiraju' 'Arijit Mukherjee' data_datam1 _database_code_depnum_ccdc_archive 'CCDC 805639' #TrackingRef '3574_web_deposit_cif_file_0_ArijitMukherjee_1293084986.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; 4,4'-bipyridyl:4-hydroxybenzoic acid co-crystal form 1 ; _chemical_melting_point ? _chemical_formula_moiety 'C10 H8 N2, 2(C7 H6 O3)' _chemical_formula_sum 'C24 H20 N2 O6' _chemical_formula_weight 432.42 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.472(2) _cell_length_b 24.646(5) _cell_length_c 7.1110(10) _cell_angle_alpha 90.00 _cell_angle_beta 93.28(3) _cell_angle_gamma 90.00 _cell_volume 2007.3(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4180 _cell_measurement_theta_min 1.7 _cell_measurement_theta_max 27.5 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.431 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 904 _exptl_absorpt_coefficient_mu 0.104 # Permitted for _exptl_absorpt_correction_type : # analytical 'analytical from crystal shape' # Example: de Meulenaer&Tompa: ABST # cylinder 'cylindrical' # gaussian 'Gaussian from crystal shape' # Example: PLATON/ABSG # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # Example: SADABS, MULABS # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # Example: PLATON/ABSP # refdelf 'refined from delta-F' # Example: SHELXA, # sphere 'spherical' # Example: PLATON/ABSS _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9694 _exptl_absorpt_correction_T_max 0.9897 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ; _diffrn_ambient_temperature 150(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 Mercury375R (2x2 bin mode' _diffrn_measurement_method 'profile data from \w-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17862 _diffrn_reflns_av_R_equivalents 0.0952 _diffrn_reflns_av_sigmaI/netI 0.0696 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 25.10 _reflns_number_total 3582 _reflns_number_gt 2675 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(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^)+(0.0768P)^2^+0.8017P] 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 3582 _refine_ls_number_parameters 299 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0935 _refine_ls_R_factor_gt 0.0632 _refine_ls_wR_factor_ref 0.1827 _refine_ls_wR_factor_gt 0.1486 _refine_ls_goodness_of_fit_ref 1.131 _refine_ls_restrained_S_all 1.131 _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 0.0351(3) 0.75259(12) 0.6163(4) 0.0294(7) Uani 1 1 d . . . C2 C 0.1556(3) 0.74474(13) 0.6401(4) 0.0308(7) Uani 1 1 d . . . H4 H 0.2064 0.7751 0.6538 0.037 Uiso 1 1 calc R . . C3 C 0.2004(3) 0.69309(13) 0.6435(4) 0.0295(7) Uani 1 1 d . . . H5 H 0.2825 0.6880 0.6598 0.035 Uiso 1 1 calc R . . C4 C 0.1274(3) 0.64782(12) 0.6234(4) 0.0276(7) Uani 1 1 d . . . C5 C 0.0071(3) 0.65633(13) 0.6018(4) 0.0309(7) Uani 1 1 d . . . H3 H -0.0440 0.6260 0.5903 0.037 Uiso 1 1 calc R . . C6 C -0.0383(3) 0.70779(13) 0.5971(4) 0.0316(7) Uani 1 1 d . . . H2 H -0.1203 0.7129 0.5805 0.038 Uiso 1 1 calc R . . C7 C 0.1744(3) 0.59281(12) 0.6246(4) 0.0277(7) Uani 1 1 d . . . C8 C 0.3059(3) 0.44846(12) 0.6423(4) 0.0281(7) Uani 1 1 d . . . C9 C 0.3580(3) 0.39409(12) 0.6518(4) 0.0259(7) Uani 1 1 d . . . C10 C 0.4785(3) 0.38806(13) 0.6434(4) 0.0296(7) Uani 1 1 d . . . H8 H 0.5263 0.4193 0.6339 0.036 Uiso 1 1 calc R . . C11 C 0.5291(3) 0.33731(13) 0.6486(4) 0.0316(7) Uani 1 1 d . . . H9 H 0.6113 0.3339 0.6425 0.038 Uiso 1 1 calc R . . C12 C 0.4608(3) 0.29102(12) 0.6626(4) 0.0281(7) Uani 1 1 d . . . C13 C 0.3404(3) 0.29685(13) 0.6738(5) 0.0327(7) Uani 1 1 d . . . H11 H 0.2930 0.2656 0.6863 0.039 Uiso 1 1 calc R . . C14 C 0.2894(3) 0.34770(12) 0.6668(4) 0.0301(7) Uani 1 1 d . . . H12 H 0.2072 0.3511 0.6722 0.036 Uiso 1 1 calc R . . C15 C 0.2617(3) 0.14617(13) 0.6220(5) 0.0342(8) Uani 1 1 d . . . H13 H 0.2130 0.1772 0.6045 0.041 Uiso 1 1 calc R . . C16 C 0.2100(3) 0.09579(12) 0.6139(4) 0.0309(7) Uani 1 1 d . . . H16 H 0.1279 0.0926 0.5906 0.037 Uiso 1 1 calc R . . C17 C 0.2790(2) 0.04928(12) 0.6401(4) 0.0255(7) Uani 1 1 d . . . C18 C 0.3987(3) 0.05718(12) 0.6716(4) 0.0289(7) Uani 1 1 d . . . H15 H 0.4498 0.0270 0.6887 0.035 Uiso 1 1 calc R . . C19 C 0.4422(3) 0.10958(13) 0.6775(4) 0.0323(7) Uani 1 1 d . . . H14 H 0.5240 0.1142 0.7005 0.039 Uiso 1 1 calc R . . C20 C 0.2272(2) -0.00585(12) 0.6354(4) 0.0253(6) Uani 1 1 d . . . C21 C 0.1145(3) -0.01487(12) 0.6895(4) 0.0295(7) Uani 1 1 d . . . H17 H 0.0684 0.0145 0.7300 0.035 Uiso 1 1 calc R . . C22 C 0.0701(3) -0.06688(13) 0.6838(4) 0.0340(8) Uani 1 1 d . . . H18 H -0.0068 -0.0724 0.7232 0.041 Uiso 1 1 calc R . . C23 C 0.2370(3) -0.10100(13) 0.5725(4) 0.0324(7) Uani 1 1 d . . . H19 H 0.2805 -0.1310 0.5306 0.039 Uiso 1 1 calc R . . C24 C 0.2885(3) -0.05088(12) 0.5750(4) 0.0302(7) Uani 1 1 d . . . H20 H 0.3658 -0.0468 0.5357 0.036 Uiso 1 1 calc R . . N1 N 0.3765(2) 0.15408(10) 0.6530(4) 0.0310(6) Uani 1 1 d . . . N2 N 0.1289(2) -0.10996(10) 0.6260(4) 0.0307(6) Uani 1 1 d . . . O1 O -0.01445(18) 0.80230(9) 0.6083(3) 0.0365(6) Uani 1 1 d . . . H1 H 0.0380 0.8261 0.6104 0.055 Uiso 1 1 calc R . . O2 O 0.28512(19) 0.58745(10) 0.6128(3) 0.0356(6) Uani 1 1 d D . . O3 O 0.10801(18) 0.55214(9) 0.6389(3) 0.0349(6) Uani 1 1 d . . . O4 O 0.19415(18) 0.45273(9) 0.6362(3) 0.0359(6) Uani 1 1 d D . . O5 O 0.37101(18) 0.48975(9) 0.6402(3) 0.0386(6) Uani 1 1 d . . . O6 O 0.51390(18) 0.24280(9) 0.6663(4) 0.0388(6) Uani 1 1 d . . . H10 H 0.4635 0.2180 0.6628 0.058 Uiso 1 1 calc R . . H6 H 0.314(6) 0.5581(17) 0.649(10) 0.18(3) Uiso 1 1 d D . . H7 H 0.167(4) 0.4851(11) 0.642(7) 0.12(2) Uiso 1 1 d 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 0.0321(17) 0.0260(17) 0.0300(16) -0.0013(13) 0.0016(14) 0.0026(13) C2 0.0278(17) 0.0301(17) 0.0340(17) -0.0005(14) -0.0013(13) -0.0063(13) C3 0.0250(16) 0.0308(17) 0.0326(16) 0.0003(14) 0.0015(13) -0.0023(12) C4 0.0250(16) 0.0290(17) 0.0286(15) -0.0001(13) 0.0002(13) -0.0020(12) C5 0.0246(16) 0.0290(17) 0.0388(17) -0.0022(14) 0.0011(14) -0.0064(12) C6 0.0240(16) 0.0329(18) 0.0376(18) 0.0004(14) -0.0007(13) -0.0013(13) C7 0.0278(16) 0.0296(17) 0.0257(15) 0.0011(13) 0.0017(13) -0.0026(13) C8 0.0249(16) 0.0268(16) 0.0326(16) -0.0023(13) 0.0023(13) -0.0040(12) C9 0.0236(15) 0.0288(16) 0.0251(14) -0.0002(13) -0.0001(12) -0.0011(12) C10 0.0253(16) 0.0286(17) 0.0351(16) -0.0002(13) 0.0021(13) -0.0043(13) C11 0.0219(15) 0.0363(18) 0.0366(18) -0.0016(14) 0.0011(14) -0.0009(13) C12 0.0252(16) 0.0272(16) 0.0319(16) -0.0001(13) 0.0018(13) 0.0018(12) C13 0.0265(16) 0.0273(16) 0.0445(19) -0.0010(14) 0.0033(14) -0.0049(13) C14 0.0202(15) 0.0327(18) 0.0372(18) -0.0021(14) 0.0002(13) -0.0037(12) C15 0.0323(18) 0.0289(17) 0.0408(18) 0.0012(15) -0.0031(14) 0.0057(13) C16 0.0240(16) 0.0311(18) 0.0376(17) 0.0005(14) 0.0010(13) 0.0033(13) C17 0.0222(15) 0.0305(17) 0.0237(14) 0.0000(13) 0.0018(12) 0.0006(12) C18 0.0245(16) 0.0260(16) 0.0363(17) 0.0031(13) 0.0016(13) 0.0041(12) C19 0.0228(15) 0.0364(18) 0.0376(17) -0.0004(15) -0.0002(13) -0.0003(13) C20 0.0245(15) 0.0267(16) 0.0245(15) 0.0002(12) -0.0001(12) 0.0013(12) C21 0.0245(16) 0.0272(17) 0.0368(17) -0.0036(14) 0.0019(13) 0.0030(13) C22 0.0266(16) 0.0373(19) 0.0383(18) 0.0004(15) 0.0028(14) -0.0028(14) C23 0.0332(17) 0.0283(17) 0.0357(17) -0.0022(14) 0.0024(14) 0.0046(13) C24 0.0261(16) 0.0311(17) 0.0335(16) 0.0019(14) 0.0031(13) 0.0019(13) N1 0.0300(14) 0.0268(14) 0.0358(14) 0.0010(11) -0.0013(12) 0.0006(11) N2 0.0306(14) 0.0281(14) 0.0329(14) 0.0004(11) -0.0020(11) -0.0006(11) O1 0.0297(12) 0.0282(12) 0.0511(14) -0.0012(11) -0.0019(11) -0.0003(9) O2 0.0231(11) 0.0318(13) 0.0526(14) 0.0021(11) 0.0067(10) -0.0008(9) O3 0.0277(12) 0.0284(12) 0.0487(14) 0.0015(10) 0.0021(10) -0.0050(9) O4 0.0242(12) 0.0307(13) 0.0529(15) 0.0011(11) 0.0023(10) 0.0016(10) O5 0.0292(12) 0.0265(12) 0.0598(15) -0.0017(11) 0.0017(11) -0.0069(9) O6 0.0304(12) 0.0255(12) 0.0604(16) 0.0005(11) 0.0006(12) 0.0018(9) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O1 1.351(4) . ? C1 C6 1.390(4) . ? C1 C2 1.396(4) . ? C2 C3 1.373(4) . ? C2 H4 0.9500 . ? C3 C4 1.398(4) . ? C3 H5 0.9500 . ? C4 C5 1.395(4) . ? C4 C7 1.459(4) . ? C5 C6 1.371(4) . ? C5 H3 0.9500 . ? C6 H2 0.9500 . ? C7 O3 1.267(3) . ? C7 O2 1.284(4) . ? C8 O5 1.263(3) . ? C8 O4 1.284(4) . ? C8 C9 1.467(4) . ? C9 C14 1.395(4) . ? C9 C10 1.395(4) . ? C10 C11 1.379(4) . ? C10 H8 0.9500 . ? C11 C12 1.391(4) . ? C11 H9 0.9500 . ? C12 O6 1.335(4) . ? C12 C13 1.396(4) . ? C13 C14 1.383(4) . ? C13 H11 0.9500 . ? C14 H12 0.9500 . ? C15 N1 1.337(4) . ? C15 C16 1.376(4) . ? C15 H13 0.9500 . ? C16 C17 1.399(4) . ? C16 H16 0.9500 . ? C17 C18 1.392(4) . ? C17 C20 1.483(4) . ? C18 C19 1.385(4) . ? C18 H15 0.9500 . ? C19 N1 1.336(4) . ? C19 H14 0.9500 . ? C20 C21 1.388(4) . ? C20 C24 1.395(4) . ? C21 C22 1.379(4) . ? C21 H17 0.9500 . ? C22 N2 1.336(4) . ? C22 H18 0.9500 . ? C23 N2 1.336(4) . ? C23 C24 1.369(4) . ? C23 H19 0.9500 . ? C24 H20 0.9500 . ? O1 H1 0.8400 . ? O2 H6 0.83(2) . ? O4 H7 0.86(2) . ? O6 H10 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 O1 C1 C6 117.7(3) . . ? O1 C1 C2 122.8(3) . . ? C6 C1 C2 119.4(3) . . ? C3 C2 C1 119.9(3) . . ? C3 C2 H4 120.1 . . ? C1 C2 H4 120.1 . . ? C2 C3 C4 121.1(3) . . ? C2 C3 H5 119.5 . . ? C4 C3 H5 119.5 . . ? C5 C4 C3 118.3(3) . . ? C5 C4 C7 120.2(3) . . ? C3 C4 C7 121.4(3) . . ? C6 C5 C4 120.9(3) . . ? C6 C5 H3 119.6 . . ? C4 C5 H3 119.6 . . ? C5 C6 C1 120.4(3) . . ? C5 C6 H2 119.8 . . ? C1 C6 H2 119.8 . . ? O3 C7 O2 121.7(3) . . ? O3 C7 C4 120.8(3) . . ? O2 C7 C4 117.5(3) . . ? O5 C8 O4 121.6(3) . . ? O5 C8 C9 119.8(3) . . ? O4 C8 C9 118.7(3) . . ? C14 C9 C10 118.7(3) . . ? C14 C9 C8 121.5(3) . . ? C10 C9 C8 119.8(3) . . ? C11 C10 C9 120.8(3) . . ? C11 C10 H8 119.6 . . ? C9 C10 H8 119.6 . . ? C10 C11 C12 120.5(3) . . ? C10 C11 H9 119.7 . . ? C12 C11 H9 119.7 . . ? O6 C12 C11 118.2(3) . . ? O6 C12 C13 122.8(3) . . ? C11 C12 C13 118.9(3) . . ? C14 C13 C12 120.6(3) . . ? C14 C13 H11 119.7 . . ? C12 C13 H11 119.7 . . ? C13 C14 C9 120.5(3) . . ? C13 C14 H12 119.8 . . ? C9 C14 H12 119.8 . . ? N1 C15 C16 123.8(3) . . ? N1 C15 H13 118.1 . . ? C16 C15 H13 118.1 . . ? C15 C16 C17 119.6(3) . . ? C15 C16 H16 120.2 . . ? C17 C16 H16 120.2 . . ? C18 C17 C16 116.9(3) . . ? C18 C17 C20 121.5(3) . . ? C16 C17 C20 121.6(3) . . ? C19 C18 C17 119.1(3) . . ? C19 C18 H15 120.5 . . ? C17 C18 H15 120.5 . . ? N1 C19 C18 124.2(3) . . ? N1 C19 H14 117.9 . . ? C18 C19 H14 117.9 . . ? C21 C20 C24 116.9(3) . . ? C21 C20 C17 121.3(3) . . ? C24 C20 C17 121.8(3) . . ? C22 C21 C20 119.3(3) . . ? C22 C21 H17 120.4 . . ? C20 C21 H17 120.4 . . ? N2 C22 C21 123.8(3) . . ? N2 C22 H18 118.1 . . ? C21 C22 H18 118.1 . . ? N2 C23 C24 123.6(3) . . ? N2 C23 H19 118.2 . . ? C24 C23 H19 118.2 . . ? C23 C24 C20 119.8(3) . . ? C23 C24 H20 120.1 . . ? C20 C24 H20 120.1 . . ? C19 N1 C15 116.4(3) . . ? C22 N2 C23 116.7(3) . . ? C1 O1 H1 109.5 . . ? C7 O2 H6 117(5) . . ? C8 O4 H7 116(4) . . ? C12 O6 H10 109.5 . . ? 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 O1 C1 C2 C3 -178.8(3) . . . . ? C6 C1 C2 C3 0.2(5) . . . . ? C1 C2 C3 C4 0.1(5) . . . . ? C2 C3 C4 C5 -0.7(5) . . . . ? C2 C3 C4 C7 179.2(3) . . . . ? C3 C4 C5 C6 1.2(5) . . . . ? C7 C4 C5 C6 -178.8(3) . . . . ? C4 C5 C6 C1 -0.9(5) . . . . ? O1 C1 C6 C5 179.2(3) . . . . ? C2 C1 C6 C5 0.2(5) . . . . ? C5 C4 C7 O3 -12.3(5) . . . . ? C3 C4 C7 O3 167.8(3) . . . . ? C5 C4 C7 O2 168.5(3) . . . . ? C3 C4 C7 O2 -11.5(4) . . . . ? O5 C8 C9 C14 175.8(3) . . . . ? O4 C8 C9 C14 -4.2(4) . . . . ? O5 C8 C9 C10 -5.1(4) . . . . ? O4 C8 C9 C10 174.9(3) . . . . ? C14 C9 C10 C11 0.4(5) . . . . ? C8 C9 C10 C11 -178.8(3) . . . . ? C9 C10 C11 C12 -0.1(5) . . . . ? C10 C11 C12 O6 179.7(3) . . . . ? C10 C11 C12 C13 -0.8(5) . . . . ? O6 C12 C13 C14 -179.1(3) . . . . ? C11 C12 C13 C14 1.5(5) . . . . ? C12 C13 C14 C9 -1.2(5) . . . . ? C10 C9 C14 C13 0.3(5) . . . . ? C8 C9 C14 C13 179.4(3) . . . . ? N1 C15 C16 C17 0.4(5) . . . . ? C15 C16 C17 C18 -0.7(4) . . . . ? C15 C16 C17 C20 179.1(3) . . . . ? C16 C17 C18 C19 0.8(4) . . . . ? C20 C17 C18 C19 -179.0(3) . . . . ? C17 C18 C19 N1 -0.7(5) . . . . ? C18 C17 C20 C21 150.2(3) . . . . ? C16 C17 C20 C21 -29.5(4) . . . . ? C18 C17 C20 C24 -30.4(4) . . . . ? C16 C17 C20 C24 149.8(3) . . . . ? C24 C20 C21 C22 0.9(4) . . . . ? C17 C20 C21 C22 -179.7(3) . . . . ? C20 C21 C22 N2 -1.0(5) . . . . ? N2 C23 C24 C20 -0.1(5) . . . . ? C21 C20 C24 C23 -0.4(4) . . . . ? C17 C20 C24 C23 -179.8(3) . . . . ? C18 C19 N1 C15 0.3(5) . . . . ? C16 C15 N1 C19 -0.2(5) . . . . ? C21 C22 N2 C23 0.4(5) . . . . ? C24 C23 N2 C22 0.2(5) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.10 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.274 _refine_diff_density_min -0.283 _refine_diff_density_rms 0.076 # Attachment '3575_web_deposit_cif_file_1_ArijitMukherjee_1293084986.cif' data_datam2 _database_code_depnum_ccdc_archive 'CCDC 805640' #TrackingRef '3575_web_deposit_cif_file_1_ArijitMukherjee_1293084986.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; 4,4'-bipyridyl:4-hydroxybenzoicacid form 2 ; _chemical_melting_point ? _chemical_formula_moiety 'C10 H8 N2, 2(C7 H6 O3)' _chemical_formula_sum 'C24 H20 N2 O6' _chemical_formula_weight 432.42 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' 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 13.983(2) _cell_length_b 11.6119(19) _cell_length_c 13.524(2) _cell_angle_alpha 90.00 _cell_angle_beta 114.143(8) _cell_angle_gamma 90.00 _cell_volume 2003.9(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 11625 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.7 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.433 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 904 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9694 _exptl_absorpt_correction_T_max 0.9896 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 Mercury375R (2x2 bin mode)' _diffrn_measurement_method 'profile data from \w-scans' _diffrn_detector_area_resol_mean 13.6612 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10286 _diffrn_reflns_av_R_equivalents 0.0312 _diffrn_reflns_av_sigmaI/netI 0.0222 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.19 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2297 _reflns_number_gt 2023 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(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^)+(0.0550P)^2^+1.0892P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2297 _refine_ls_number_parameters 147 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0427 _refine_ls_R_factor_gt 0.0374 _refine_ls_wR_factor_ref 0.1024 _refine_ls_wR_factor_gt 0.0989 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _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 C6 C 0.30560(9) 0.90096(10) 0.41518(9) 0.0218(3) Uani 1 1 d . . . C7 C 0.27894(9) 0.78966(10) 0.37467(10) 0.0226(3) Uani 1 1 d . . . H5 H 0.2480 0.7380 0.4076 0.027 Uiso 1 1 calc R . . C8 C 0.29749(9) 0.75455(10) 0.28653(9) 0.0207(2) Uani 1 1 d . . . H6 H 0.2803 0.6782 0.2600 0.025 Uiso 1 1 calc R . . C9 C 0.34108(9) 0.82968(10) 0.23591(9) 0.0197(2) Uani 1 1 d . . . C10 C 0.36587(10) 0.94135(10) 0.27585(10) 0.0233(3) Uani 1 1 d . . . H8 H 0.3944 0.9938 0.2412 0.028 Uiso 1 1 calc R . . C11 C 0.34940(10) 0.97692(10) 0.36533(10) 0.0233(3) Uani 1 1 d . . . H9 H 0.3679 1.0528 0.3927 0.028 Uiso 1 1 calc R . . C12 C 0.36054(9) 0.79415(10) 0.14017(9) 0.0211(3) Uani 1 1 d . . . O1 O 0.36440(7) 0.68289(7) 0.12745(7) 0.0273(2) Uani 1 1 d . . . H7 H 0.3781 0.6695 0.0736 0.041 Uiso 1 1 calc R . . O2 O 0.37303(8) 0.86420(8) 0.07861(7) 0.0305(2) Uani 1 1 d . . . O3 O 0.28873(8) 0.93067(8) 0.50394(8) 0.0313(2) Uani 1 1 d . . . H10 H 0.3136 0.9965 0.5250 0.047 Uiso 1 1 calc R . . C1 C -0.00370(9) 0.77230(10) 0.13653(10) 0.0240(3) Uani 1 1 d . . . H3 H -0.0406 0.7080 0.1470 0.029 Uiso 1 1 calc R . . C2 C 0.03052(9) 0.77168(11) 0.05388(10) 0.0237(3) Uani 1 1 d . . . H4 H 0.0151 0.7065 0.0075 0.028 Uiso 1 1 calc R . . C3 C 0.01640(8) 0.86785(10) 0.20419(9) 0.0201(2) Uani 1 1 d . . . C4 C 0.06920(9) 0.96036(10) 0.18395(9) 0.0215(3) Uani 1 1 d . . . H1 H 0.0823 1.0284 0.2265 0.026 Uiso 1 1 calc R . . C5 C 0.10241(9) 0.95161(10) 0.10057(10) 0.0227(3) Uani 1 1 d . . . H2 H 0.1398 1.0144 0.0883 0.027 Uiso 1 1 calc R . . N1 N 0.08435(8) 0.85887(9) 0.03651(8) 0.0227(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C6 0.0273(6) 0.0206(6) 0.0204(5) 0.0008(4) 0.0126(5) 0.0022(4) C7 0.0283(6) 0.0189(6) 0.0241(6) 0.0016(4) 0.0142(5) -0.0013(4) C8 0.0241(6) 0.0168(5) 0.0214(5) 0.0003(4) 0.0093(4) 0.0002(4) C9 0.0217(5) 0.0197(6) 0.0186(5) 0.0015(4) 0.0092(4) 0.0019(4) C10 0.0281(6) 0.0207(6) 0.0239(6) 0.0023(4) 0.0135(5) -0.0019(5) C11 0.0302(6) 0.0175(5) 0.0238(6) -0.0018(4) 0.0127(5) -0.0027(5) C12 0.0230(5) 0.0217(6) 0.0197(5) 0.0017(4) 0.0097(5) 0.0026(4) O1 0.0447(5) 0.0206(4) 0.0238(4) -0.0003(3) 0.0212(4) 0.0027(4) O2 0.0478(6) 0.0239(5) 0.0299(5) 0.0061(4) 0.0263(4) 0.0065(4) O3 0.0545(6) 0.0213(4) 0.0305(5) -0.0054(4) 0.0299(5) -0.0064(4) C1 0.0239(6) 0.0226(6) 0.0276(6) -0.0024(5) 0.0127(5) -0.0017(4) C2 0.0238(6) 0.0232(6) 0.0237(6) -0.0032(5) 0.0093(5) 0.0016(4) C3 0.0192(5) 0.0218(6) 0.0196(5) 0.0008(4) 0.0084(4) 0.0025(4) C4 0.0243(6) 0.0196(5) 0.0210(5) -0.0009(4) 0.0097(5) 0.0006(4) C5 0.0248(6) 0.0216(6) 0.0235(6) 0.0024(4) 0.0117(5) 0.0013(4) N1 0.0242(5) 0.0247(5) 0.0203(5) 0.0010(4) 0.0104(4) 0.0039(4) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C6 O3 1.3592(14) . ? C6 C7 1.3937(16) . ? C6 C11 1.3947(16) . ? C7 C8 1.3810(16) . ? C7 H5 0.9500 . ? C8 C9 1.3938(16) . ? C8 H6 0.9500 . ? C9 C10 1.3929(16) . ? C9 C12 1.4864(15) . ? C10 C11 1.3843(17) . ? C10 H8 0.9500 . ? C11 H9 0.9500 . ? C12 O2 1.2265(14) . ? C12 O1 1.3074(15) . ? O1 H7 0.8400 . ? O3 H10 0.8400 . ? C1 C2 1.3842(17) . ? C1 C3 1.3918(16) . ? C1 H3 0.9500 . ? C2 N1 1.3385(16) . ? C2 H4 0.9500 . ? C3 C4 1.3926(16) . ? C3 C3 1.487(2) 2 ? C4 C5 1.3877(16) . ? C4 H1 0.9500 . ? C5 N1 1.3399(15) . ? C5 H2 0.9500 . ? 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 O3 C6 C7 117.86(10) . . ? O3 C6 C11 122.38(11) . . ? C7 C6 C11 119.75(11) . . ? C8 C7 C6 119.90(11) . . ? C8 C7 H5 120.1 . . ? C6 C7 H5 120.1 . . ? C7 C8 C9 120.90(11) . . ? C7 C8 H6 119.6 . . ? C9 C8 H6 119.6 . . ? C10 C9 C8 118.79(10) . . ? C10 C9 C12 119.41(10) . . ? C8 C9 C12 121.79(10) . . ? C11 C10 C9 120.85(11) . . ? C11 C10 H8 119.6 . . ? C9 C10 H8 119.6 . . ? C10 C11 C6 119.79(11) . . ? C10 C11 H9 120.1 . . ? C6 C11 H9 120.1 . . ? O2 C12 O1 122.75(11) . . ? O2 C12 C9 122.34(11) . . ? O1 C12 C9 114.90(10) . . ? C12 O1 H7 109.5 . . ? C6 O3 H10 109.5 . . ? C2 C1 C3 119.44(11) . . ? C2 C1 H3 120.3 . . ? C3 C1 H3 120.3 . . ? N1 C2 C1 122.88(11) . . ? N1 C2 H4 118.6 . . ? C1 C2 H4 118.6 . . ? C1 C3 C4 117.80(10) . . ? C1 C3 C3 119.98(8) . 2 ? C4 C3 C3 122.20(8) . 2 ? C5 C4 C3 118.94(11) . . ? C5 C4 H1 120.5 . . ? C3 C4 H1 120.5 . . ? N1 C5 C4 123.16(11) . . ? N1 C5 H2 118.4 . . ? C4 C5 H2 118.4 . . ? C2 N1 C5 117.72(10) . . ? 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 O3 C6 C7 C8 -178.13(11) . . . . ? C11 C6 C7 C8 1.02(18) . . . . ? C6 C7 C8 C9 -1.11(18) . . . . ? C7 C8 C9 C10 0.04(17) . . . . ? C7 C8 C9 C12 -179.26(10) . . . . ? C8 C9 C10 C11 1.13(18) . . . . ? C12 C9 C10 C11 -179.55(11) . . . . ? C9 C10 C11 C6 -1.22(18) . . . . ? O3 C6 C11 C10 179.24(11) . . . . ? C7 C6 C11 C10 0.14(18) . . . . ? C10 C9 C12 O2 -18.30(17) . . . . ? C8 C9 C12 O2 161.01(12) . . . . ? C10 C9 C12 O1 161.00(11) . . . . ? C8 C9 C12 O1 -19.70(16) . . . . ? C3 C1 C2 N1 1.16(18) . . . . ? C2 C1 C3 C4 1.08(17) . . . . ? C2 C1 C3 C3 -177.71(12) . . . 2 ? C1 C3 C4 C5 -2.28(17) . . . . ? C3 C3 C4 C5 176.49(12) 2 . . . ? C3 C4 C5 N1 1.39(18) . . . . ? C1 C2 N1 C5 -2.11(17) . . . . ? C4 C5 N1 C2 0.81(17) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.293 _refine_diff_density_min -0.190 _refine_diff_density_rms 0.042 # Attachment '3576_web_deposit_cif_file_2_ArijitMukherjee_1293084986.cif' data_datam3 _database_code_depnum_ccdc_archive 'CCDC 805641' #TrackingRef '3576_web_deposit_cif_file_2_ArijitMukherjee_1293084986.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; 4,4'-bipyridyl:4-hydroxybenzoicacid form 3 ; _chemical_melting_point ? _chemical_formula_moiety '2(C10 H8 N2), C7 H6 O3' _chemical_formula_sum 'C27 H22 N4 O3' _chemical_formula_weight 450.49 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 7.702(3) _cell_length_b 9.503(5) _cell_length_c 16.765(5) _cell_angle_alpha 84.074(7) _cell_angle_beta 77.313(7) _cell_angle_gamma 67.731(7) _cell_volume 1107.6(8) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9941 _cell_measurement_theta_min 2.9 _cell_measurement_theta_max 27.8 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.351 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9734 _exptl_absorpt_correction_T_max 0.9910 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 Mercury375R (2x2 bin mode) ; _diffrn_measurement_method 'profile data from \w-scans' _diffrn_detector_area_resol_mean 13.6612 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11374 _diffrn_reflns_av_R_equivalents 0.0376 _diffrn_reflns_av_sigmaI/netI 0.0442 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.36 _diffrn_reflns_theta_max 27.48 _reflns_number_total 5041 _reflns_number_gt 4046 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(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^)+(0.0796P)^2^+0.1839P] 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 10(10) _refine_ls_number_reflns 5041 _refine_ls_number_parameters 617 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0670 _refine_ls_R_factor_gt 0.0524 _refine_ls_wR_factor_ref 0.1398 _refine_ls_wR_factor_gt 0.1297 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _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 N1 N 0.0837(5) 0.1895(4) 0.6245(2) 0.0380(9) Uani 1 1 d . B . N2 N -0.0342(5) 0.2207(4) 0.2120(2) 0.0381(8) Uani 1 1 d . . . C15 C -0.0187(6) 0.3175(5) 0.5894(3) 0.0428(11) Uani 1 1 d . . . H15 H -0.0817 0.4060 0.6215 0.051 Uiso 1 1 calc R . . C16 C -0.0379(6) 0.3282(4) 0.5089(2) 0.0350(9) Uani 1 1 d . B . H16 H -0.1113 0.4227 0.4869 0.042 Uiso 1 1 calc R . . C17 C 0.0500(5) 0.2008(4) 0.4599(2) 0.0243(8) Uani 1 1 d . . . C18 C 0.1570(6) 0.0664(4) 0.4972(2) 0.0296(8) Uani 1 1 d . B . H18 H 0.2206 -0.0244 0.4670 0.036 Uiso 1 1 calc R . . C19 C 0.1696(6) 0.0667(4) 0.5774(3) 0.0345(9) Uani 1 1 d . . . H19 H 0.2436 -0.0257 0.6011 0.041 Uiso 1 1 calc R B . C20 C -0.0617(6) 0.3441(4) 0.2525(2) 0.0369(9) Uani 1 1 d . B . H20 H -0.1054 0.4399 0.2251 0.044 Uiso 1 1 calc R . . C21 C -0.0321(5) 0.3437(4) 0.3304(2) 0.0301(8) Uani 1 1 d . . . H21 H -0.0517 0.4362 0.3544 0.036 Uiso 1 1 calc R A 1 C22 C 0.0272(5) 0.2063(4) 0.3741(2) 0.0234(8) Uani 1 1 d . B 1 C23 C 0.0578(6) 0.0764(4) 0.3326(3) 0.0307(9) Uani 1 1 d . . . H23 H 0.0999 -0.0209 0.3586 0.037 Uiso 1 1 calc R B 1 C24 C 0.0268(6) 0.0894(5) 0.2541(3) 0.0380(10) Uani 1 1 d . B . H24 H 0.0505 -0.0016 0.2276 0.046 Uiso 1 1 calc R . . N7 N 0.6229(5) 0.1289(4) 0.6249(2) 0.0378(8) Uani 1 1 d . . . N8 N 0.5066(5) 0.1413(4) 0.2137(2) 0.0320(8) Uani 1 1 d . . . C45 C 0.4896(5) 0.2672(4) 0.2482(2) 0.0336(9) Uani 1 1 d . D . H45 H 0.4590 0.3596 0.2170 0.040 Uiso 1 1 calc R . . C46 C 0.5143(5) 0.2707(4) 0.3279(2) 0.0291(8) Uani 1 1 d . . . H46 H 0.4998 0.3635 0.3500 0.035 Uiso 1 1 calc R C 1 C47 C 0.5605(5) 0.1364(4) 0.3746(2) 0.0202(7) Uani 1 1 d . D 1 C48 C 0.5788(5) 0.0058(4) 0.3384(2) 0.0297(8) Uani 1 1 d . . . H48 H 0.6109 -0.0886 0.3678 0.036 Uiso 1 1 calc R D 1 C49 C 0.5501(6) 0.0135(4) 0.2594(2) 0.0335(9) Uani 1 1 d . D . H49 H 0.5620 -0.0775 0.2362 0.040 Uiso 1 1 calc R . . C50 C 0.5250(6) 0.2568(5) 0.5875(3) 0.0397(10) Uani 1 1 d . . . H50 H 0.4677 0.3478 0.6178 0.048 Uiso 1 1 calc R . . C51 C 0.5024(6) 0.2643(4) 0.5066(2) 0.0307(8) Uani 1 1 d . . . H51 H 0.4312 0.3582 0.4832 0.037 Uiso 1 1 calc R E 1 C52 C 0.5845(5) 0.1337(4) 0.4607(2) 0.0243(8) Uani 1 1 d . D 1 C53 C 0.6850(6) 0.0011(4) 0.4989(2) 0.0325(9) Uani 1 1 d . . . H53 H 0.7431 -0.0916 0.4700 0.039 Uiso 1 1 calc R D 1 C54 C 0.7006(6) 0.0041(5) 0.5801(3) 0.0360(9) Uani 1 1 d . D . H54 H 0.7709 -0.0885 0.6049 0.043 Uiso 1 1 calc R . . N5 N 0.4754(5) 0.6324(4) 0.7304(2) 0.0334(8) Uani 1 1 d . . . N6 N 0.5983(5) 0.6270(4) 1.1390(2) 0.0375(8) Uani 1 1 d . . . C35 C 0.4366(7) 0.7610(5) 0.7682(3) 0.0397(10) Uani 1 1 d . G . H35 H 0.3961 0.8544 0.7383 0.048 Uiso 1 1 calc R . . C36 C 0.4525(6) 0.7656(4) 0.8493(2) 0.0323(9) Uani 1 1 d . . . H36 H 0.4235 0.8598 0.8736 0.039 Uiso 1 1 calc R F 1 C37 C 0.5109(5) 0.6312(4) 0.8932(2) 0.0242(8) Uani 1 1 d . G 1 C38 C 0.5496(6) 0.4967(4) 0.8552(2) 0.0314(9) Uani 1 1 d . . . H38 H 0.5886 0.4018 0.8837 0.038 Uiso 1 1 calc R G 1 C39 C 0.5298(6) 0.5045(4) 0.7741(3) 0.0338(9) Uani 1 1 d . G . H39 H 0.5570 0.4119 0.7484 0.041 Uiso 1 1 calc R . . C40 C 0.4834(6) 0.7491(5) 1.1061(3) 0.0357(9) Uani 1 1 d . . . H40 H 0.4197 0.8373 1.1384 0.043 Uiso 1 1 calc R . . C41 C 0.4487(5) 0.7580(4) 1.0269(2) 0.0299(8) Uani 1 1 d . . . H41 H 0.3655 0.8498 1.0063 0.036 Uiso 1 1 calc R H 1 C42 C 0.5384(5) 0.6297(4) 0.9790(2) 0.0220(7) Uani 1 1 d . G 1 C43 C 0.6550(5) 0.5008(4) 1.0140(2) 0.0307(8) Uani 1 1 d . . . H43 H 0.7172 0.4093 0.9843 0.037 Uiso 1 1 calc R G 1 C44 C 0.6810(6) 0.5054(5) 1.0931(2) 0.0364(9) Uani 1 1 d . G . H44 H 0.7635 0.4153 1.1155 0.044 Uiso 1 1 calc R . . N3 N -0.0695(5) 0.7178(4) 0.7276(2) 0.0370(8) Uani 1 1 d . . . N4 N 0.0522(5) 0.6825(4) 1.1396(2) 0.0332(8) Uani 1 1 d . . . C25 C -0.0526(5) 0.8127(4) 1.1061(2) 0.0331(9) Uani 1 1 d . . . H25 H -0.1090 0.9012 1.1384 0.040 Uiso 1 1 calc R . . C26 C -0.0829(5) 0.8249(4) 1.0268(2) 0.0286(8) Uani 1 1 d . . . H26 H -0.1605 0.9194 1.0062 0.034 Uiso 1 1 calc R . . C27 C 0.0013(5) 0.6975(4) 0.9771(2) 0.0244(8) Uani 1 1 d . . . C28 C 0.1104(5) 0.5635(4) 1.0124(2) 0.0278(8) Uani 1 1 d . . . H28 H 0.1701 0.4731 0.9816 0.033 Uiso 1 1 calc R . . C29 C 0.1318(6) 0.5616(4) 1.0916(3) 0.0338(9) Uani 1 1 d . . . H29 H 0.2082 0.4683 1.1137 0.041 Uiso 1 1 calc R . . C30 C -0.1038(6) 0.8437(5) 0.7681(3) 0.0375(9) Uani 1 1 d . . . H30 H -0.1433 0.9391 0.7400 0.045 Uiso 1 1 calc R . . C31 C -0.0848(6) 0.8422(4) 0.8484(2) 0.0324(9) Uani 1 1 d . . . H31 H -0.1123 0.9349 0.8741 0.039 Uiso 1 1 calc R . . C32 C -0.0255(5) 0.7048(4) 0.8913(2) 0.0235(8) Uani 1 1 d . . . C33 C 0.0106(6) 0.5737(4) 0.8494(3) 0.0318(9) Uani 1 1 d . . . H33 H 0.0515 0.4765 0.8756 0.038 Uiso 1 1 calc R . . C34 C -0.0138(6) 0.5871(5) 0.7697(3) 0.0364(10) Uani 1 1 d . . . H34 H 0.0110 0.4964 0.7427 0.044 Uiso 1 1 calc R . . O4 O 0.3646(4) 0.1438(4) 1.08420(19) 0.0444(8) Uani 1 1 d . . . H4O H 0.4394 0.1369 1.1154 0.067 Uiso 1 1 calc R . . O5 O 0.6005(4) 0.1713(3) 0.98773(18) 0.0357(7) Uani 1 1 d . . . O6 O -0.0146(4) 0.1719(3) 0.78736(18) 0.0348(6) Uani 1 1 d . . . H6O H 0.0424 0.1699 0.7384 0.052 Uiso 1 1 calc R . . C8 C 0.3266(5) 0.1616(4) 0.9488(2) 0.0228(7) Uani 1 1 d . . . C9 C 0.3982(5) 0.1654(3) 0.8654(2) 0.0224(7) Uani 1 1 d . . . H9 H 0.5234 0.1665 0.8465 0.027 Uiso 1 1 calc R . . C10 C 0.2875(5) 0.1677(4) 0.8088(2) 0.0268(8) Uani 1 1 d . . . H10 H 0.3370 0.1694 0.7517 0.032 Uiso 1 1 calc R . . C11 C 0.1048(5) 0.1676(3) 0.8375(2) 0.0225(7) Uani 1 1 d . . . C12 C 0.0333(5) 0.1602(4) 0.9207(2) 0.0252(8) Uani 1 1 d . . . H12 H -0.0904 0.1560 0.9394 0.030 Uiso 1 1 calc R . . C13 C 0.1441(5) 0.1589(3) 0.9770(2) 0.0214(7) Uani 1 1 d . . . H13 H 0.0948 0.1563 1.0340 0.026 Uiso 1 1 calc R . . C14 C 0.4465(5) 0.1589(4) 1.0086(2) 0.0240(8) Uani 1 1 d . . . O1 O 0.2014(4) 0.6670(4) 0.26949(19) 0.0453(8) Uani 1 1 d . . . H1O H 0.1240 0.6837 0.2381 0.068 Uiso 1 1 calc R . . O2 O -0.0567(3) 0.6925(3) 0.36564(18) 0.0346(6) Uani 1 1 d . . . O3 O 0.5732(4) 0.6516(3) 0.56800(18) 0.0352(7) Uani 1 1 d . . . H3O H 0.5188 0.6461 0.6168 0.053 Uiso 1 1 calc R . . C1 C 0.2313(5) 0.6695(4) 0.4045(2) 0.0224(7) Uani 1 1 d . . . C2 C 0.1574(5) 0.6693(4) 0.4888(2) 0.0234(8) Uani 1 1 d . . . H2 H 0.0302 0.6728 0.5076 0.028 Uiso 1 1 calc R . . C3 C 0.2682(5) 0.6639(4) 0.5452(2) 0.0247(8) Uani 1 1 d . . . H3 H 0.2164 0.6649 0.6021 0.030 Uiso 1 1 calc R . . C4 C 0.4550(5) 0.6570(3) 0.5177(2) 0.0233(8) Uani 1 1 d . . . C5 C 0.5305(5) 0.6565(4) 0.4336(2) 0.0252(8) Uani 1 1 d . . . H5 H 0.6581 0.6520 0.4147 0.030 Uiso 1 1 calc R . . C6 C 0.4180(5) 0.6625(4) 0.3779(2) 0.0228(8) Uani 1 1 d . . . H6 H 0.4696 0.6618 0.3209 0.027 Uiso 1 1 calc R . . C7 C 0.1089(5) 0.6769(3) 0.3460(2) 0.0217(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.041(2) 0.050(2) 0.028(2) 0.0015(16) -0.0129(17) -0.0190(17) N2 0.0315(17) 0.055(2) 0.0239(19) -0.0005(15) -0.0083(14) -0.0103(16) C15 0.046(2) 0.047(2) 0.032(2) -0.0121(18) -0.0127(19) -0.0065(19) C16 0.043(2) 0.0306(18) 0.027(2) -0.0052(15) -0.0151(17) -0.0024(16) C17 0.0271(18) 0.0273(17) 0.021(2) -0.0027(14) -0.0045(15) -0.0123(14) C18 0.0350(19) 0.0228(17) 0.031(2) 0.0003(14) -0.0154(16) -0.0054(15) C19 0.040(2) 0.034(2) 0.030(2) 0.0041(16) -0.0158(17) -0.0096(17) C20 0.043(2) 0.042(2) 0.030(2) 0.0143(16) -0.0171(17) -0.0187(18) C21 0.0354(19) 0.0272(17) 0.0283(19) 0.0031(14) -0.0102(15) -0.0110(15) C22 0.0213(16) 0.0236(16) 0.026(2) -0.0010(14) -0.0073(15) -0.0078(13) C23 0.037(2) 0.0243(17) 0.031(2) -0.0021(14) -0.0153(16) -0.0062(15) C24 0.038(2) 0.042(2) 0.031(2) -0.0133(17) -0.0101(18) -0.0058(18) N7 0.042(2) 0.051(2) 0.0209(19) 0.0011(15) -0.0104(16) -0.0166(17) N8 0.0326(17) 0.0502(19) 0.0181(18) 0.0013(14) -0.0112(14) -0.0178(15) C45 0.037(2) 0.0359(19) 0.0240(19) 0.0046(15) -0.0095(16) -0.0081(16) C46 0.0325(19) 0.0250(16) 0.0288(19) 0.0018(14) -0.0098(16) -0.0080(15) C47 0.0184(15) 0.0258(17) 0.0180(18) 0.0025(13) -0.0068(14) -0.0090(13) C48 0.040(2) 0.0242(16) 0.028(2) -0.0007(14) -0.0122(16) -0.0115(15) C49 0.039(2) 0.041(2) 0.025(2) -0.0078(15) -0.0088(16) -0.0166(17) C50 0.052(3) 0.039(2) 0.028(2) -0.0067(17) -0.0092(19) -0.0160(19) C51 0.041(2) 0.0261(17) 0.025(2) 0.0019(14) -0.0130(16) -0.0092(16) C52 0.0274(18) 0.0283(17) 0.020(2) 0.0009(14) -0.0110(15) -0.0103(15) C53 0.034(2) 0.0323(19) 0.024(2) -0.0019(15) -0.0109(16) -0.0014(16) C54 0.035(2) 0.043(2) 0.026(2) 0.0016(17) -0.0151(17) -0.0065(17) N5 0.0412(19) 0.0438(18) 0.0193(18) -0.0019(14) -0.0129(16) -0.0161(16) N6 0.0349(18) 0.060(2) 0.0222(19) 0.0044(16) -0.0085(15) -0.0221(16) C35 0.055(3) 0.034(2) 0.027(2) 0.0045(17) -0.020(2) -0.0092(19) C36 0.041(2) 0.0268(18) 0.028(2) -0.0033(15) -0.0138(17) -0.0063(16) C37 0.0236(17) 0.0248(17) 0.026(2) 0.0016(15) -0.0133(16) -0.0070(14) C38 0.045(2) 0.0267(17) 0.028(2) 0.0040(14) -0.0162(17) -0.0160(16) C39 0.049(2) 0.0325(19) 0.027(2) -0.0025(15) -0.0150(18) -0.0188(17) C40 0.041(2) 0.045(2) 0.026(2) -0.0070(17) -0.0072(17) -0.0190(18) C41 0.0327(19) 0.0315(18) 0.029(2) -0.0041(15) -0.0108(16) -0.0118(15) C42 0.0241(16) 0.0274(17) 0.0186(19) 0.0012(14) -0.0077(14) -0.0124(14) C43 0.0324(19) 0.0327(18) 0.0283(19) 0.0029(15) -0.0124(16) -0.0108(16) C44 0.0320(19) 0.047(2) 0.031(2) 0.0112(17) -0.0176(17) -0.0129(17) N3 0.0403(19) 0.049(2) 0.0232(19) -0.0035(15) -0.0074(16) -0.0171(16) N4 0.0306(17) 0.0447(19) 0.027(2) -0.0005(15) -0.0068(15) -0.0160(15) C25 0.0304(19) 0.042(2) 0.0252(19) -0.0106(15) -0.0027(15) -0.0103(16) C26 0.0304(18) 0.0305(17) 0.0240(18) -0.0029(14) -0.0097(15) -0.0071(15) C27 0.0243(17) 0.0260(17) 0.024(2) -0.0021(14) -0.0072(15) -0.0093(14) C28 0.0333(19) 0.0274(17) 0.0228(18) -0.0008(13) -0.0075(15) -0.0101(15) C29 0.038(2) 0.0336(19) 0.031(2) 0.0053(15) -0.0137(17) -0.0112(16) C30 0.046(2) 0.040(2) 0.030(2) 0.0069(16) -0.0166(18) -0.0168(18) C31 0.047(2) 0.0304(18) 0.025(2) 0.0022(15) -0.0145(17) -0.0158(17) C32 0.0226(17) 0.0292(18) 0.022(2) -0.0042(15) -0.0040(15) -0.0123(14) C33 0.041(2) 0.0288(18) 0.029(2) -0.0033(15) -0.0099(17) -0.0143(16) C34 0.044(2) 0.038(2) 0.025(2) -0.0116(16) -0.0045(17) -0.0122(18) O4 0.0408(16) 0.085(2) 0.0192(16) 0.0016(15) -0.0087(13) -0.0358(16) O5 0.0291(14) 0.0451(16) 0.0363(16) 0.0031(12) -0.0101(12) -0.0163(12) O6 0.0422(16) 0.0413(15) 0.0286(16) 0.0027(12) -0.0168(13) -0.0192(13) C8 0.0236(16) 0.0220(15) 0.022(2) 0.0008(13) -0.0065(15) -0.0064(13) C9 0.0241(16) 0.0176(15) 0.0228(19) 0.0006(13) -0.0019(14) -0.0065(13) C10 0.0323(19) 0.0194(16) 0.024(2) 0.0038(14) -0.0036(17) -0.0069(14) C11 0.0278(17) 0.0181(16) 0.021(2) 0.0002(13) -0.0077(15) -0.0060(14) C12 0.0269(17) 0.0228(17) 0.024(2) -0.0050(14) -0.0021(15) -0.0077(14) C13 0.0250(17) 0.0218(16) 0.0161(18) -0.0006(13) -0.0026(14) -0.0079(13) C14 0.0240(17) 0.0207(16) 0.028(2) 0.0005(14) -0.0082(15) -0.0076(14) O1 0.0300(14) 0.082(2) 0.0244(17) -0.0016(15) -0.0092(13) -0.0192(15) O2 0.0248(13) 0.0400(14) 0.0419(17) -0.0044(12) -0.0080(12) -0.0134(11) O3 0.0383(15) 0.0454(16) 0.0249(16) -0.0004(13) -0.0132(12) -0.0147(13) C1 0.0240(16) 0.0212(15) 0.0206(19) -0.0005(13) -0.0035(14) -0.0071(13) C2 0.0204(16) 0.0191(15) 0.026(2) -0.0024(13) -0.0003(14) -0.0040(13) C3 0.0326(19) 0.0259(17) 0.0141(18) -0.0044(13) 0.0002(15) -0.0108(15) C4 0.0312(18) 0.0158(15) 0.022(2) 0.0004(13) -0.0112(16) -0.0045(14) C5 0.0250(17) 0.0226(17) 0.027(2) 0.0056(14) -0.0063(15) -0.0085(14) C6 0.0243(16) 0.0237(17) 0.0175(19) -0.0005(14) -0.0004(14) -0.0077(14) C7 0.0242(17) 0.0203(16) 0.0205(19) -0.0014(13) -0.0046(14) -0.0077(13) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 N1 C15 1.333(6) . ? N1 C19 1.341(5) . ? N2 C24 1.340(6) . ? N2 C20 1.340(6) . ? C15 C16 1.378(6) . ? C15 H15 0.9500 . ? C16 C17 1.393(5) . ? C16 H16 0.9500 . ? C17 C18 1.402(5) . ? C17 C22 1.480(6) . ? C18 C19 1.370(6) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 C21 1.374(6) . ? C20 H20 0.9500 . ? C21 C22 1.396(5) . ? C21 H21 0.9500 . ? C22 C23 1.396(5) . ? C23 C24 1.373(6) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? N7 C54 1.334(5) . ? N7 C50 1.340(6) . ? N8 C45 1.333(5) . ? N8 C49 1.337(5) . ? C45 C46 1.394(6) . ? C45 H45 0.9500 . ? C46 C47 1.393(5) . ? C46 H46 0.9500 . ? C47 C48 1.384(5) . ? C47 C52 1.492(5) . ? C48 C49 1.379(6) . ? C48 H48 0.9500 . ? C49 H49 0.9500 . ? C50 C51 1.396(6) . ? C50 H50 0.9500 . ? C51 C52 1.386(5) . ? C51 H51 0.9500 . ? C52 C53 1.381(5) . ? C53 C54 1.398(6) . ? C53 H53 0.9500 . ? C54 H54 0.9500 . ? N5 C39 1.325(5) . ? N5 C35 1.336(5) . ? N6 C40 1.319(5) . ? N6 C44 1.322(6) . ? C35 C36 1.398(6) . ? C35 H35 0.9500 . ? C36 C37 1.376(5) . ? C36 H36 0.9500 . ? C37 C38 1.387(5) . ? C37 C42 1.497(6) . ? C38 C39 1.392(6) . ? C38 H38 0.9500 . ? C39 H39 0.9500 . ? C40 C41 1.399(6) . ? C40 H40 0.9500 . ? C41 C42 1.388(5) . ? C41 H41 0.9500 . ? C42 C43 1.379(5) . ? C43 C44 1.391(5) . ? C43 H43 0.9500 . ? C44 H44 0.9500 . ? N3 C34 1.331(5) . ? N3 C30 1.347(5) . ? N4 C29 1.336(5) . ? N4 C25 1.341(5) . ? C25 C26 1.386(6) . ? C25 H25 0.9500 . ? C26 C27 1.398(5) . ? C26 H26 0.9500 . ? C27 C28 1.390(5) . ? C27 C32 1.488(6) . ? C28 C29 1.371(6) . ? C28 H28 0.9500 . ? C29 H29 0.9500 . ? C30 C31 1.384(6) . ? C30 H30 0.9500 . ? C31 C32 1.389(5) . ? C31 H31 0.9500 . ? C32 C33 1.399(5) . ? C33 C34 1.376(6) . ? C33 H33 0.9500 . ? C34 H34 0.9500 . ? O4 C14 1.305(5) . ? O4 H4O 0.8400 . ? O5 C14 1.208(4) . ? O6 C11 1.363(4) . ? O6 H6O 0.8400 . ? C8 C9 1.388(5) . ? C8 C13 1.390(5) . ? C8 C14 1.498(5) . ? C9 C10 1.402(5) . ? C9 H9 0.9500 . ? C10 C11 1.384(5) . ? C10 H10 0.9500 . ? C11 C12 1.388(5) . ? C12 C13 1.400(5) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? O1 C7 1.318(5) . ? O1 H1O 0.8400 . ? O2 C7 1.200(4) . ? O3 C4 1.354(4) . ? O3 H3O 0.8400 . ? C1 C6 1.387(5) . ? C1 C2 1.403(5) . ? C1 C7 1.482(5) . ? C2 C3 1.391(5) . ? C2 H2 0.9500 . ? C3 C4 1.389(5) . ? C3 H3 0.9500 . ? C4 C5 1.402(5) . ? C5 C6 1.391(5) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? 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 C15 N1 C19 116.6(4) . . ? C24 N2 C20 114.3(4) . . ? N1 C15 C16 123.4(4) . . ? N1 C15 H15 118.3 . . ? C16 C15 H15 118.3 . . ? C15 C16 C17 120.2(4) . . ? C15 C16 H16 119.9 . . ? C17 C16 H16 119.9 . . ? C16 C17 C18 116.1(4) . . ? C16 C17 C22 121.9(3) . . ? C18 C17 C22 122.1(3) . . ? C19 C18 C17 119.7(4) . . ? C19 C18 H18 120.1 . . ? C17 C18 H18 120.1 . . ? N1 C19 C18 124.0(4) . . ? N1 C19 H19 118.0 . . ? C18 C19 H19 118.0 . . ? N2 C20 C21 125.4(3) . . ? N2 C20 H20 117.3 . . ? C21 C20 H20 117.3 . . ? C20 C21 C22 119.5(4) . . ? C20 C21 H21 120.3 . . ? C22 C21 H21 120.3 . . ? C23 C22 C21 115.8(4) . . ? C23 C22 C17 122.7(3) . . ? C21 C22 C17 121.5(3) . . ? C24 C23 C22 120.0(4) . . ? C24 C23 H23 120.0 . . ? C22 C23 H23 120.0 . . ? N2 C24 C23 125.0(4) . . ? N2 C24 H24 117.5 . . ? C23 C24 H24 117.5 . . ? C54 N7 C50 116.0(4) . . ? C45 N8 C49 116.6(3) . . ? N8 C45 C46 123.5(3) . . ? N8 C45 H45 118.3 . . ? C46 C45 H45 118.3 . . ? C47 C46 C45 119.2(3) . . ? C47 C46 H46 120.4 . . ? C45 C46 H46 120.4 . . ? C48 C47 C46 117.1(3) . . ? C48 C47 C52 121.2(3) . . ? C46 C47 C52 121.6(3) . . ? C49 C48 C47 119.6(3) . . ? C49 C48 H48 120.2 . . ? C47 C48 H48 120.2 . . ? N8 C49 C48 123.9(4) . . ? N8 C49 H49 118.0 . . ? C48 C49 H49 118.0 . . ? N7 C50 C51 123.8(4) . . ? N7 C50 H50 118.1 . . ? C51 C50 H50 118.1 . . ? C52 C51 C50 119.5(4) . . ? C52 C51 H51 120.2 . . ? C50 C51 H51 120.2 . . ? C53 C52 C51 117.1(4) . . ? C53 C52 C47 121.8(3) . . ? C51 C52 C47 121.1(3) . . ? C52 C53 C54 119.5(4) . . ? C52 C53 H53 120.2 . . ? C54 C53 H53 120.2 . . ? N7 C54 C53 124.0(4) . . ? N7 C54 H54 118.0 . . ? C53 C54 H54 118.0 . . ? C39 N5 C35 116.6(4) . . ? C40 N6 C44 116.1(4) . . ? N5 C35 C36 123.5(4) . . ? N5 C35 H35 118.3 . . ? C36 C35 H35 118.3 . . ? C37 C36 C35 118.9(4) . . ? C37 C36 H36 120.6 . . ? C35 C36 H36 120.6 . . ? C36 C37 C38 118.3(4) . . ? C36 C37 C42 120.8(3) . . ? C38 C37 C42 120.9(3) . . ? C37 C38 C39 118.4(3) . . ? C37 C38 H38 120.8 . . ? C39 C38 H38 120.8 . . ? N5 C39 C38 124.3(4) . . ? N5 C39 H39 117.8 . . ? C38 C39 H39 117.8 . . ? N6 C40 C41 124.6(4) . . ? N6 C40 H40 117.7 . . ? C41 C40 H40 117.7 . . ? C42 C41 C40 118.6(4) . . ? C42 C41 H41 120.7 . . ? C40 C41 H41 120.7 . . ? C43 C42 C41 116.9(4) . . ? C43 C42 C37 121.4(3) . . ? C41 C42 C37 121.7(3) . . ? C42 C43 C44 119.6(4) . . ? C42 C43 H43 120.2 . . ? C44 C43 H43 120.2 . . ? N6 C44 C43 124.1(4) . . ? N6 C44 H44 117.9 . . ? C43 C44 H44 117.9 . . ? C34 N3 C30 115.7(4) . . ? C29 N4 C25 116.3(4) . . ? N4 C25 C26 123.4(4) . . ? N4 C25 H25 118.3 . . ? C26 C25 H25 118.3 . . ? C25 C26 C27 119.7(3) . . ? C25 C26 H26 120.1 . . ? C27 C26 H26 120.1 . . ? C28 C27 C26 116.3(4) . . ? C28 C27 C32 121.8(3) . . ? C26 C27 C32 121.9(3) . . ? C29 C28 C27 120.0(4) . . ? C29 C28 H28 120.0 . . ? C27 C28 H28 120.0 . . ? N4 C29 C28 124.2(4) . . ? N4 C29 H29 117.9 . . ? C28 C29 H29 117.9 . . ? N3 C30 C31 123.8(4) . . ? N3 C30 H30 118.1 . . ? C31 C30 H30 118.1 . . ? C30 C31 C32 119.8(4) . . ? C30 C31 H31 120.1 . . ? C32 C31 H31 120.1 . . ? C31 C32 C33 116.6(4) . . ? C31 C32 C27 121.6(3) . . ? C33 C32 C27 121.8(3) . . ? C34 C33 C32 119.2(4) . . ? C34 C33 H33 120.4 . . ? C32 C33 H33 120.4 . . ? N3 C34 C33 124.9(4) . . ? N3 C34 H34 117.5 . . ? C33 C34 H34 117.5 . . ? C14 O4 H4O 109.5 . . ? C11 O6 H6O 109.5 . . ? C9 C8 C13 120.1(3) . . ? C9 C8 C14 120.1(3) . . ? C13 C8 C14 119.8(3) . . ? C8 C9 C10 120.6(3) . . ? C8 C9 H9 119.7 . . ? C10 C9 H9 119.7 . . ? C11 C10 C9 118.9(3) . . ? C11 C10 H10 120.6 . . ? C9 C10 H10 120.6 . . ? O6 C11 C10 123.2(3) . . ? O6 C11 C12 115.7(3) . . ? C10 C11 C12 121.1(3) . . ? C11 C12 C13 119.8(3) . . ? C11 C12 H12 120.1 . . ? C13 C12 H12 120.1 . . ? C8 C13 C12 119.6(3) . . ? C8 C13 H13 120.2 . . ? C12 C13 H13 120.2 . . ? O5 C14 O4 124.9(4) . . ? O5 C14 C8 122.6(3) . . ? O4 C14 C8 112.5(3) . . ? C7 O1 H1O 109.5 . . ? C4 O3 H3O 109.5 . . ? C6 C1 C2 119.0(3) . . ? C6 C1 C7 121.5(3) . . ? C2 C1 C7 119.5(3) . . ? C3 C2 C1 120.8(3) . . ? C3 C2 H2 119.6 . . ? C1 C2 H2 119.6 . . ? C4 C3 C2 119.6(3) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? O3 C4 C3 123.7(3) . . ? O3 C4 C5 116.2(3) . . ? C3 C4 C5 120.0(3) . . ? C6 C5 C4 119.8(3) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C1 C6 C5 120.7(3) . . ? C1 C6 H6 119.6 . . ? C5 C6 H6 119.6 . . ? O2 C7 O1 123.4(4) . . ? O2 C7 C1 124.1(3) . . ? O1 C7 C1 112.4(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C19 N1 C15 C16 -0.4(7) . . . . ? N1 C15 C16 C17 0.8(7) . . . . ? C15 C16 C17 C18 -0.6(6) . . . . ? C15 C16 C17 C22 177.8(4) . . . . ? C16 C17 C18 C19 0.1(6) . . . . ? C22 C17 C18 C19 -178.3(4) . . . . ? C15 N1 C19 C18 -0.2(6) . . . . ? C17 C18 C19 N1 0.3(6) . . . . ? C24 N2 C20 C21 0.2(6) . . . . ? N2 C20 C21 C22 -1.7(6) . . . . ? C20 C21 C22 C23 1.9(5) . . . . ? C20 C21 C22 C17 -176.3(3) . . . . ? C16 C17 C22 C23 -158.5(4) . . . . ? C18 C17 C22 C23 19.8(5) . . . . ? C16 C17 C22 C21 19.6(5) . . . . ? C18 C17 C22 C21 -162.0(3) . . . . ? C21 C22 C23 C24 -0.9(6) . . . . ? C17 C22 C23 C24 177.4(4) . . . . ? C20 N2 C24 C23 1.0(6) . . . . ? C22 C23 C24 N2 -0.6(7) . . . . ? C49 N8 C45 C46 -0.1(6) . . . . ? N8 C45 C46 C47 0.4(6) . . . . ? C45 C46 C47 C48 -0.1(5) . . . . ? C45 C46 C47 C52 -178.7(3) . . . . ? C46 C47 C48 C49 -0.4(5) . . . . ? C52 C47 C48 C49 178.1(4) . . . . ? C45 N8 C49 C48 -0.4(6) . . . . ? C47 C48 C49 N8 0.7(6) . . . . ? C54 N7 C50 C51 -0.1(6) . . . . ? N7 C50 C51 C52 -0.1(7) . . . . ? C50 C51 C52 C53 0.4(6) . . . . ? C50 C51 C52 C47 178.9(4) . . . . ? C48 C47 C52 C53 21.9(6) . . . . ? C46 C47 C52 C53 -159.6(3) . . . . ? C48 C47 C52 C51 -156.5(3) . . . . ? C46 C47 C52 C51 22.0(5) . . . . ? C51 C52 C53 C54 -0.4(6) . . . . ? C47 C52 C53 C54 -178.9(4) . . . . ? C50 N7 C54 C53 0.0(6) . . . . ? C52 C53 C54 N7 0.3(7) . . . . ? C39 N5 C35 C36 0.6(6) . . . . ? N5 C35 C36 C37 -0.1(7) . . . . ? C35 C36 C37 C38 -0.7(6) . . . . ? C35 C36 C37 C42 177.3(4) . . . . ? C36 C37 C38 C39 0.8(6) . . . . ? C42 C37 C38 C39 -177.1(4) . . . . ? C35 N5 C39 C38 -0.5(6) . . . . ? C37 C38 C39 N5 -0.3(6) . . . . ? C44 N6 C40 C41 -1.6(6) . . . . ? N6 C40 C41 C42 0.9(6) . . . . ? C40 C41 C42 C43 0.8(5) . . . . ? C40 C41 C42 C37 -179.0(3) . . . . ? C36 C37 C42 C43 -157.5(3) . . . . ? C38 C37 C42 C43 20.4(5) . . . . ? C36 C37 C42 C41 22.2(5) . . . . ? C38 C37 C42 C41 -159.9(3) . . . . ? C41 C42 C43 C44 -1.5(5) . . . . ? C37 C42 C43 C44 178.2(3) . . . . ? C40 N6 C44 C43 0.7(6) . . . . ? C42 C43 C44 N6 0.9(6) . . . . ? C29 N4 C25 C26 1.2(6) . . . . ? N4 C25 C26 C27 -1.3(6) . . . . ? C25 C26 C27 C28 0.9(5) . . . . ? C25 C26 C27 C32 -179.5(3) . . . . ? C26 C27 C28 C29 -0.5(5) . . . . ? C32 C27 C28 C29 179.9(3) . . . . ? C25 N4 C29 C28 -0.9(6) . . . . ? C27 C28 C29 N4 0.5(6) . . . . ? C34 N3 C30 C31 -0.3(6) . . . . ? N3 C30 C31 C32 0.7(7) . . . . ? C30 C31 C32 C33 -0.5(6) . . . . ? C30 C31 C32 C27 178.5(4) . . . . ? C28 C27 C32 C31 -161.1(3) . . . . ? C26 C27 C32 C31 19.4(6) . . . . ? C28 C27 C32 C33 17.9(6) . . . . ? C26 C27 C32 C33 -161.7(3) . . . . ? C31 C32 C33 C34 0.0(6) . . . . ? C27 C32 C33 C34 -179.0(4) . . . . ? C30 N3 C34 C33 -0.2(7) . . . . ? C32 C33 C34 N3 0.3(7) . . . . ? C13 C8 C9 C10 0.4(5) . . . . ? C14 C8 C9 C10 179.9(3) . . . . ? C8 C9 C10 C11 0.6(5) . . . . ? C9 C10 C11 O6 179.1(3) . . . . ? C9 C10 C11 C12 -2.1(5) . . . . ? O6 C11 C12 C13 -178.5(3) . . . . ? C10 C11 C12 C13 2.6(5) . . . . ? C9 C8 C13 C12 0.0(5) . . . . ? C14 C8 C13 C12 -179.5(3) . . . . ? C11 C12 C13 C8 -1.5(5) . . . . ? C9 C8 C14 O5 5.7(5) . . . . ? C13 C8 C14 O5 -174.9(3) . . . . ? C9 C8 C14 O4 -175.2(3) . . . . ? C13 C8 C14 O4 4.3(4) . . . . ? C6 C1 C2 C3 0.7(5) . . . . ? C7 C1 C2 C3 -179.4(3) . . . . ? C1 C2 C3 C4 -0.7(5) . . . . ? C2 C3 C4 O3 180.0(3) . . . . ? C2 C3 C4 C5 0.4(5) . . . . ? O3 C4 C5 C6 -179.7(3) . . . . ? C3 C4 C5 C6 -0.2(5) . . . . ? C2 C1 C6 C5 -0.5(5) . . . . ? C7 C1 C6 C5 179.6(3) . . . . ? C4 C5 C6 C1 0.2(5) . . . . ? C6 C1 C7 O2 -175.2(3) . . . . ? C2 C1 C7 O2 5.0(5) . . . . ? C6 C1 C7 O1 3.7(4) . . . . ? C2 C1 C7 O1 -176.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.418 _refine_diff_density_min -0.260 _refine_diff_density_rms 0.052 # Attachment '3577_web_deposit_cif_file_3_ArijitMukherjee_1293084986.cif' data_datam4 _database_code_depnum_ccdc_archive 'CCDC 805642' #TrackingRef '3577_web_deposit_cif_file_3_ArijitMukherjee_1293084986.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; 4phenylpyridine:4-hydroxybenzoicacid ; _chemical_melting_point ? _chemical_formula_moiety '2(C11 H9 N), C7 H6 O3' _chemical_formula_sum 'C29 H24 N2 O3' _chemical_formula_weight 448.50 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 7.5084(7) _cell_length_b 18.0404(16) _cell_length_c 19.0238(17) _cell_angle_alpha 66.060(5) _cell_angle_beta 84.424(6) _cell_angle_gamma 83.795(6) _cell_volume 2337.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 18780 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.6 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.275 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9755 _exptl_absorpt_correction_T_max 0.9917 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 Mercury375R (2x2 bin mode) ; _diffrn_measurement_method 'profile data from \w-scans' _diffrn_detector_area_resol_mean 13.6612 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25067 _diffrn_reflns_av_R_equivalents 0.0611 _diffrn_reflns_av_sigmaI/netI 0.0830 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.04 _diffrn_reflns_theta_max 27.48 _reflns_number_total 10707 _reflns_number_gt 6382 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(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^)+(0.0537P)^2^+0.3916P] 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 10707 _refine_ls_number_parameters 805 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1188 _refine_ls_R_factor_gt 0.0610 _refine_ls_wR_factor_ref 0.1402 _refine_ls_wR_factor_gt 0.1196 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _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 H4 H 0.370(3) 0.8941(12) 0.4401(13) 0.020(6) Uiso 1 1 d . . . H52 H 0.352(3) 0.0611(14) 0.4308(13) 0.029(6) Uiso 1 1 d . . . H54 H 0.417(3) 0.1632(15) 0.1737(13) 0.035(7) Uiso 1 1 d . . . H49 H 0.387(3) 0.3364(14) 0.2807(13) 0.033(7) Uiso 1 1 d . . . H47 H -0.425(3) 1.3159(14) -0.1235(13) 0.034(7) Uiso 1 1 d . . . H7 H 0.575(3) 1.0196(12) 0.1778(12) 0.020(5) Uiso 1 1 d . . . H15 H 1.362(3) 0.5579(14) -0.0996(13) 0.032(6) Uiso 1 1 d . . . H30 H 0.719(3) 0.2846(13) 0.5445(12) 0.030(6) Uiso 1 1 d . . . H58 H 0.194(3) 0.3733(15) 0.1835(14) 0.042(7) Uiso 1 1 d . . . H21 H 1.075(3) 0.6846(15) -0.3173(13) 0.035(7) Uiso 1 1 d . . . H10 H 1.207(3) 0.4613(13) 0.3196(13) 0.025(6) Uiso 1 1 d . . . H3 H 0.154(3) 0.9397(13) 0.3411(13) 0.033(6) Uiso 1 1 d . . . H51 H 0.317(3) 0.1109(14) 0.2982(13) 0.034(7) Uiso 1 1 d . . . H13 H 1.062(3) 0.5810(13) 0.0599(13) 0.024(6) Uiso 1 1 d . . . H48 H 0.421(3) 0.2835(15) 0.4140(14) 0.042(7) Uiso 1 1 d . . . H29 H 0.445(3) 0.2422(15) 0.6214(15) 0.042(7) Uiso 1 1 d . . . H6 H 0.775(3) 0.9776(14) 0.2748(13) 0.036(7) Uiso 1 1 d . . . H16 H 1.283(3) 0.6263(15) -0.2276(15) 0.044(7) Uiso 1 1 d . . . H36 H 0.028(3) 0.4331(16) 0.5969(14) 0.040(7) Uiso 1 1 d . . . H46 H -0.663(3) 1.3680(15) -0.2050(14) 0.041(7) Uiso 1 1 d . . . H43 H -0.492(3) 1.0874(15) -0.1156(13) 0.037(7) Uiso 1 1 d . . . H11 H 1.437(3) 0.5078(13) 0.2210(13) 0.030(6) Uiso 1 1 d . . . H45 H -0.815(3) 1.2820(15) -0.2435(14) 0.043(7) Uiso 1 1 d . . . H32 H 0.159(3) 0.1967(14) 0.6293(13) 0.033(6) Uiso 1 1 d . . . H40 H -0.118(3) 1.2544(14) -0.1243(14) 0.034(7) Uiso 1 1 d . . . H56 H 0.252(3) 0.3473(14) -0.0248(14) 0.040(7) Uiso 1 1 d . . . H35 H -0.241(3) 0.3936(15) 0.6749(14) 0.044(7) Uiso 1 1 d . . . H14 H 0.829(3) 0.5363(14) 0.1570(13) 0.034(6) Uiso 1 1 d . . . H34 H -0.298(3) 0.2576(14) 0.7327(14) 0.040(7) Uiso 1 1 d . . . H22 H 1.012(3) 0.7579(15) -0.4513(15) 0.045(8) Uiso 1 1 d . . . H55 H 0.374(3) 0.2139(14) 0.0397(14) 0.039(7) Uiso 1 1 d . . . H38 H -0.384(3) 1.0597(14) 0.0159(14) 0.040(7) Uiso 1 1 d . . . H44 H -0.725(4) 1.1438(16) -0.1999(16) 0.056(9) Uiso 1 1 d . . . H27 H 0.188(4) 0.4531(15) 0.4752(14) 0.046(7) Uiso 1 1 d . . . H25 H 1.208(3) 0.8947(14) -0.3081(14) 0.037(7) Uiso 1 1 d . . . H33 H -0.097(4) 0.1562(17) 0.7125(15) 0.054(8) Uiso 1 1 d . . . H41 H 0.133(3) 1.2013(15) -0.0477(14) 0.043(7) Uiso 1 1 d . . . H37 H -0.129(3) 1.0105(16) 0.0899(15) 0.051(8) Uiso 1 1 d . . . H57 H 0.162(3) 0.4280(16) 0.0470(14) 0.048(8) Uiso 1 1 d . . . H18 H 1.114(3) 0.8249(16) -0.1805(14) 0.043(7) Uiso 1 1 d . . . H19 H 1.193(3) 0.7503(15) -0.0543(15) 0.046(8) Uiso 1 1 d . . . H26 H 0.471(4) 0.4839(17) 0.4046(16) 0.056(8) Uiso 1 1 d . . . H6O H 1.362(4) 0.6022(19) 0.0238(19) 0.076(10) Uiso 1 1 d . . . H24 H 1.149(4) 0.9656(18) -0.4367(17) 0.066(9) Uiso 1 1 d . . . H4O H 0.791(4) 0.4148(18) 0.4150(18) 0.077(10) Uiso 1 1 d . . . H23 H 1.047(4) 0.8993(18) -0.5096(18) 0.067(9) Uiso 1 1 d . . . H1O H 0.188(5) 1.066(2) 0.083(2) 0.109(13) Uiso 1 1 d . . . H3O H 0.669(4) 0.8765(19) 0.4750(19) 0.080(11) Uiso 1 1 d . . . O3 O 0.7146(2) 0.90767(10) 0.41998(9) 0.0337(4) Uani 1 1 d . . . O1 O 0.2851(2) 1.04158(10) 0.11920(9) 0.0310(4) Uani 1 1 d . . . C42 C -0.4369(3) 1.19555(13) -0.11106(12) 0.0244(5) Uani 1 1 d . . . O2 O 0.0559(2) 1.00399(13) 0.20593(10) 0.0535(6) Uani 1 1 d . . . C5 C 0.5913(3) 0.93169(13) 0.36602(12) 0.0246(5) Uani 1 1 d . . . C3 C 0.2896(3) 0.94668(13) 0.32773(13) 0.0262(5) Uani 1 1 d . . . N3 N 0.0200(3) 1.10120(13) 0.02602(11) 0.0354(5) Uani 1 1 d . . . C2 C 0.3492(3) 0.98280(13) 0.25044(12) 0.0238(5) Uani 1 1 d . . . C41 C 0.0193(3) 1.17251(16) -0.03517(13) 0.0341(6) Uani 1 1 d . . . C1 C 0.2161(3) 1.00993(14) 0.19082(13) 0.0292(5) Uani 1 1 d . . . C45 C -0.7183(3) 1.26038(16) -0.20878(14) 0.0336(6) Uani 1 1 d . . . C4 C 0.4095(3) 0.92091(13) 0.38533(13) 0.0260(5) Uani 1 1 d . . . C43 C -0.5271(3) 1.14566(15) -0.13317(13) 0.0301(5) Uani 1 1 d . . . C6 C 0.6517(3) 0.96859(14) 0.28907(13) 0.0262(5) Uani 1 1 d . . . C7 C 0.5306(3) 0.99341(13) 0.23206(13) 0.0235(5) Uani 1 1 d . . . C39 C -0.2800(3) 1.16267(13) -0.06282(12) 0.0262(5) Uani 1 1 d . . . C46 C -0.6314(3) 1.30990(16) -0.18687(14) 0.0346(6) Uani 1 1 d . . . C47 C -0.4908(3) 1.27828(14) -0.13801(13) 0.0294(5) Uani 1 1 d . . . C38 C -0.2792(4) 1.08869(16) 0.00068(14) 0.0366(6) Uani 1 1 d . . . C40 C -0.1264(3) 1.20452(15) -0.08038(14) 0.0311(6) Uani 1 1 d . . . C37 C -0.1282(3) 1.06122(17) 0.04298(15) 0.0399(7) Uani 1 1 d . . . C44 C -0.6671(3) 1.17796(16) -0.18200(14) 0.0333(6) Uani 1 1 d . . . O4 O 0.9005(2) 0.43729(10) 0.37952(9) 0.0312(4) Uani 1 1 d . . . O6 O 1.4047(2) 0.57229(10) 0.07645(10) 0.0328(4) Uani 1 1 d . . . O5 O 0.6932(2) 0.47856(10) 0.29219(9) 0.0369(4) Uani 1 1 d . . . C10 C 1.1773(3) 0.48768(13) 0.26537(13) 0.0252(5) Uani 1 1 d . . . C8 C 0.8499(3) 0.47046(13) 0.30751(12) 0.0252(5) Uani 1 1 d . . . C9 C 0.9985(3) 0.49610(13) 0.24770(12) 0.0230(5) Uani 1 1 d . . . C11 C 1.3115(3) 0.51349(14) 0.20786(13) 0.0269(5) Uani 1 1 d . . . C14 C 0.9571(3) 0.53072(14) 0.17034(13) 0.0264(5) Uani 1 1 d . . . N1 N 1.2828(3) 0.64811(13) -0.06569(11) 0.0358(5) Uani 1 1 d . . . C17 C 1.1910(3) 0.73522(14) -0.21864(13) 0.0266(5) Uani 1 1 d . . . C12 C 1.2689(3) 0.54830(13) 0.13091(12) 0.0240(5) Uani 1 1 d . . . C18 C 1.1640(3) 0.77010(16) -0.16505(14) 0.0331(6) Uani 1 1 d . . . C16 C 1.2625(3) 0.65511(15) -0.19286(14) 0.0298(5) Uani 1 1 d . . . C13 C 1.0902(3) 0.55679(14) 0.11252(13) 0.0267(5) Uani 1 1 d . . . C20 C 1.1487(3) 0.78194(14) -0.30052(13) 0.0288(5) Uani 1 1 d . . . C15 C 1.3066(3) 0.61437(16) -0.11715(14) 0.0325(6) Uani 1 1 d . . . C21 C 1.0945(3) 0.74326(17) -0.34383(14) 0.0336(6) Uani 1 1 d . . . C22 C 1.0574(3) 0.78583(19) -0.42032(15) 0.0414(7) Uani 1 1 d . . . C25 C 1.1662(3) 0.86565(16) -0.33636(16) 0.0377(6) Uani 1 1 d . . . C23 C 1.0737(3) 0.86857(19) -0.45471(16) 0.0449(7) Uani 1 1 d . . . C19 C 1.2112(3) 0.72478(17) -0.09049(15) 0.0377(6) Uani 1 1 d . . . C24 C 1.1293(4) 0.90825(19) -0.41326(17) 0.0474(7) Uani 1 1 d . . . N4 N 0.3932(3) 0.16654(12) 0.43252(11) 0.0315(5) Uani 1 1 d . . . C50 C 0.3423(3) 0.22977(13) 0.27362(12) 0.0226(5) Uani 1 1 d . . . C53 C 0.3130(3) 0.26315(13) 0.19015(12) 0.0232(5) Uani 1 1 d . . . C58 C 0.2347(3) 0.34174(14) 0.15207(13) 0.0274(5) Uani 1 1 d . . . C54 C 0.3620(3) 0.21596(15) 0.14771(13) 0.0287(5) Uani 1 1 d . . . C48 C 0.4011(3) 0.24573(15) 0.38850(14) 0.0309(5) Uani 1 1 d . . . C51 C 0.3369(3) 0.14732(14) 0.31944(13) 0.0286(5) Uani 1 1 d . . . C55 C 0.3376(3) 0.24650(15) 0.06978(14) 0.0308(5) Uani 1 1 d . . . C49 C 0.3763(3) 0.27929(15) 0.31037(13) 0.0275(5) Uani 1 1 d . . . C57 C 0.2101(3) 0.37207(15) 0.07389(14) 0.0324(6) Uani 1 1 d . . . C56 C 0.2625(3) 0.32462(16) 0.03222(14) 0.0329(6) Uani 1 1 d . . . C52 C 0.3624(3) 0.11899(15) 0.39695(13) 0.0302(5) Uani 1 1 d . . . N2 N 0.6120(3) 0.38795(13) 0.47112(11) 0.0348(5) Uani 1 1 d . . . C31 C 0.1169(3) 0.31898(13) 0.60438(12) 0.0262(5) Uani 1 1 d . . . C28 C 0.2865(3) 0.34286(14) 0.55727(13) 0.0274(5) Uani 1 1 d . . . C33 C -0.0744(3) 0.21490(16) 0.68729(14) 0.0352(6) Uani 1 1 d . . . C32 C 0.0777(3) 0.23801(14) 0.63882(14) 0.0306(5) Uani 1 1 d . . . C36 C -0.0028(3) 0.37689(15) 0.61839(14) 0.0325(6) Uani 1 1 d . . . C30 C 0.6019(3) 0.31772(16) 0.53260(14) 0.0337(6) Uani 1 1 d . . . C35 C -0.1565(3) 0.35360(17) 0.66625(15) 0.0371(6) Uani 1 1 d . . . C29 C 0.4448(3) 0.29320(15) 0.57622(14) 0.0314(6) Uani 1 1 d . . . C34 C -0.1919(3) 0.27235(17) 0.70057(14) 0.0360(6) Uani 1 1 d . . . C27 C 0.2974(3) 0.41538(16) 0.49268(14) 0.0392(6) Uani 1 1 d . . . C26 C 0.4597(4) 0.43532(17) 0.45202(16) 0.0444(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O3 0.0334(9) 0.0439(11) 0.0228(9) -0.0119(8) -0.0067(7) 0.0003(8) O1 0.0268(9) 0.0373(10) 0.0229(9) -0.0065(7) -0.0023(7) 0.0006(8) C42 0.0240(12) 0.0286(12) 0.0187(11) -0.0083(9) 0.0007(9) -0.0010(10) O2 0.0240(10) 0.0841(15) 0.0337(11) -0.0027(10) -0.0026(8) -0.0102(10) C5 0.0291(12) 0.0228(12) 0.0234(12) -0.0112(9) -0.0057(9) 0.0040(10) C3 0.0253(12) 0.0258(12) 0.0257(13) -0.0080(10) 0.0002(10) -0.0051(10) N3 0.0270(11) 0.0479(13) 0.0264(11) -0.0103(10) -0.0036(9) 0.0006(10) C2 0.0262(12) 0.0216(11) 0.0224(12) -0.0076(9) -0.0011(9) -0.0020(10) C41 0.0291(13) 0.0465(16) 0.0238(13) -0.0108(11) -0.0010(10) -0.0045(12) C1 0.0287(13) 0.0296(13) 0.0259(13) -0.0072(10) -0.0023(10) -0.0037(11) C45 0.0306(13) 0.0450(16) 0.0236(13) -0.0128(11) -0.0090(11) 0.0076(12) C4 0.0314(13) 0.0234(12) 0.0212(12) -0.0068(10) 0.0013(10) -0.0042(10) C43 0.0299(13) 0.0284(13) 0.0316(14) -0.0120(11) -0.0036(10) 0.0017(11) C6 0.0234(12) 0.0297(13) 0.0245(13) -0.0106(10) 0.0012(10) -0.0011(10) C7 0.0262(12) 0.0236(12) 0.0203(12) -0.0091(9) 0.0022(9) -0.0020(10) C39 0.0260(12) 0.0294(13) 0.0221(12) -0.0098(10) -0.0014(9) 0.0004(10) C46 0.0396(15) 0.0293(14) 0.0312(14) -0.0101(11) -0.0055(11) 0.0078(12) C47 0.0335(13) 0.0271(13) 0.0277(13) -0.0109(10) -0.0027(10) -0.0011(11) C38 0.0316(14) 0.0370(15) 0.0315(14) -0.0024(11) -0.0046(11) -0.0051(12) C40 0.0320(13) 0.0331(14) 0.0242(13) -0.0065(11) -0.0031(10) -0.0050(11) C37 0.0356(15) 0.0436(17) 0.0304(15) -0.0041(12) -0.0094(11) 0.0025(13) C44 0.0337(14) 0.0398(15) 0.0312(14) -0.0187(12) -0.0065(11) -0.0008(12) O4 0.0297(9) 0.0372(10) 0.0227(9) -0.0063(7) -0.0050(7) -0.0057(8) O6 0.0283(9) 0.0399(10) 0.0267(9) -0.0092(8) 0.0004(7) -0.0062(8) O5 0.0243(9) 0.0504(11) 0.0292(9) -0.0084(8) -0.0058(7) -0.0011(8) C10 0.0303(13) 0.0232(12) 0.0229(13) -0.0087(10) -0.0069(10) -0.0025(10) C8 0.0299(13) 0.0212(12) 0.0229(12) -0.0065(9) -0.0060(10) -0.0003(10) C9 0.0259(12) 0.0195(11) 0.0225(12) -0.0067(9) -0.0050(9) 0.0002(10) C11 0.0241(12) 0.0288(13) 0.0286(13) -0.0110(10) -0.0057(10) -0.0026(10) C14 0.0234(12) 0.0262(13) 0.0280(13) -0.0087(10) -0.0059(10) -0.0001(10) N1 0.0283(11) 0.0462(14) 0.0285(12) -0.0105(10) 0.0012(9) -0.0054(10) C17 0.0186(11) 0.0320(13) 0.0292(13) -0.0109(10) -0.0010(9) -0.0072(10) C12 0.0260(12) 0.0204(11) 0.0256(12) -0.0093(9) -0.0016(10) -0.0018(10) C18 0.0290(13) 0.0363(15) 0.0351(15) -0.0156(12) -0.0016(11) -0.0016(12) C16 0.0270(13) 0.0313(14) 0.0295(14) -0.0102(11) -0.0008(10) -0.0046(11) C13 0.0299(13) 0.0258(12) 0.0214(13) -0.0056(10) -0.0077(10) 0.0003(10) C20 0.0206(12) 0.0307(13) 0.0321(13) -0.0101(11) -0.0009(10) -0.0001(10) C15 0.0256(13) 0.0347(15) 0.0320(14) -0.0084(11) 0.0010(10) -0.0030(11) C21 0.0293(13) 0.0383(15) 0.0346(15) -0.0169(12) -0.0030(11) 0.0013(12) C22 0.0285(14) 0.0596(19) 0.0366(16) -0.0212(14) -0.0063(11) 0.0060(13) C25 0.0285(14) 0.0369(15) 0.0429(16) -0.0099(13) -0.0049(12) -0.0041(12) C23 0.0265(14) 0.061(2) 0.0304(15) -0.0032(14) -0.0019(11) 0.0061(14) C19 0.0348(14) 0.0509(17) 0.0326(15) -0.0225(13) 0.0023(12) -0.0051(13) C24 0.0357(15) 0.0391(17) 0.0485(18) 0.0020(14) -0.0026(13) -0.0038(14) N4 0.0298(11) 0.0378(12) 0.0258(11) -0.0120(9) -0.0036(9) 0.0007(9) C50 0.0183(11) 0.0266(12) 0.0219(12) -0.0091(9) 0.0018(9) -0.0018(9) C53 0.0205(11) 0.0248(12) 0.0229(12) -0.0076(9) -0.0007(9) -0.0041(10) C58 0.0292(13) 0.0264(13) 0.0259(13) -0.0090(10) -0.0029(10) -0.0033(11) C54 0.0305(13) 0.0248(13) 0.0285(13) -0.0087(10) -0.0026(10) 0.0011(11) C48 0.0314(13) 0.0333(14) 0.0314(14) -0.0158(11) -0.0051(10) -0.0027(11) C51 0.0360(14) 0.0251(13) 0.0258(13) -0.0120(10) -0.0007(10) -0.0006(11) C55 0.0316(13) 0.0386(15) 0.0255(13) -0.0167(11) 0.0002(10) -0.0023(11) C49 0.0268(12) 0.0276(13) 0.0283(13) -0.0106(11) -0.0036(10) -0.0037(11) C57 0.0343(14) 0.0285(14) 0.0288(14) -0.0053(11) -0.0073(11) 0.0007(11) C56 0.0312(13) 0.0416(15) 0.0215(13) -0.0072(11) -0.0026(10) -0.0055(12) C52 0.0371(14) 0.0241(13) 0.0245(13) -0.0060(10) -0.0004(10) 0.0023(11) N2 0.0326(11) 0.0437(13) 0.0237(11) -0.0079(9) -0.0030(9) -0.0060(10) C31 0.0270(12) 0.0268(12) 0.0239(12) -0.0083(10) -0.0060(10) -0.0014(10) C28 0.0293(12) 0.0275(13) 0.0243(12) -0.0093(10) -0.0056(10) 0.0015(10) C33 0.0372(15) 0.0346(15) 0.0315(14) -0.0095(12) -0.0011(11) -0.0098(12) C32 0.0340(14) 0.0255(13) 0.0330(14) -0.0129(11) -0.0028(11) 0.0007(11) C36 0.0332(14) 0.0272(14) 0.0344(14) -0.0096(11) -0.0074(11) 0.0025(11) C30 0.0271(13) 0.0421(15) 0.0266(13) -0.0094(11) -0.0039(10) 0.0035(12) C35 0.0336(14) 0.0415(16) 0.0400(15) -0.0222(13) -0.0011(12) 0.0036(13) C29 0.0333(14) 0.0303(14) 0.0254(13) -0.0064(11) -0.0037(10) 0.0018(11) C34 0.0300(14) 0.0528(18) 0.0274(14) -0.0176(12) 0.0024(11) -0.0103(13) C27 0.0304(14) 0.0377(15) 0.0333(15) 0.0009(11) -0.0024(11) 0.0037(12) C26 0.0377(15) 0.0421(17) 0.0339(16) 0.0046(13) -0.0023(12) -0.0020(13) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C5 1.355(3) . ? O3 H3O 1.01(3) . ? O1 C1 1.321(3) . ? O1 H1O 1.00(4) . ? C42 C43 1.392(3) . ? C42 C47 1.394(3) . ? C42 C39 1.483(3) . ? O2 C1 1.216(3) . ? C5 C4 1.392(3) . ? C5 C6 1.392(3) . ? C3 C4 1.384(3) . ? C3 C2 1.394(3) . ? C3 H3 1.03(2) . ? N3 C37 1.333(3) . ? N3 C41 1.340(3) . ? C2 C7 1.387(3) . ? C2 C1 1.479(3) . ? C41 C40 1.383(3) . ? C41 H41 1.01(3) . ? C45 C46 1.370(3) . ? C45 C44 1.385(3) . ? C45 H45 0.97(3) . ? C4 H4 0.99(2) . ? C43 C44 1.388(3) . ? C43 H43 0.98(2) . ? C6 C7 1.383(3) . ? C6 H6 0.95(2) . ? C7 H7 0.99(2) . ? C39 C40 1.386(3) . ? C39 C38 1.390(3) . ? C46 C47 1.391(3) . ? C46 H46 0.97(2) . ? C47 H47 1.01(2) . ? C38 C37 1.382(3) . ? C38 H38 0.95(3) . ? C40 H40 0.95(2) . ? C37 H37 0.98(3) . ? C44 H44 0.97(3) . ? O4 C8 1.329(3) . ? O4 H4O 1.02(3) . ? O6 C12 1.351(3) . ? O6 H6O 0.99(3) . ? O5 C8 1.219(3) . ? C10 C11 1.379(3) . ? C10 C9 1.393(3) . ? C10 H10 0.98(2) . ? C8 C9 1.480(3) . ? C9 C14 1.398(3) . ? C11 C12 1.393(3) . ? C11 H11 0.98(2) . ? C14 C13 1.378(3) . ? C14 H14 1.00(2) . ? N1 C19 1.336(3) . ? N1 C15 1.337(3) . ? C17 C16 1.388(3) . ? C17 C18 1.389(3) . ? C17 C20 1.487(3) . ? C12 C13 1.396(3) . ? C18 C19 1.378(4) . ? C18 H18 0.96(3) . ? C16 C15 1.380(3) . ? C16 H16 0.99(3) . ? C13 H13 0.95(2) . ? C20 C21 1.387(3) . ? C20 C25 1.397(3) . ? C15 H15 0.99(2) . ? C21 C22 1.382(4) . ? C21 H21 0.99(2) . ? C22 C23 1.379(4) . ? C22 H22 1.02(3) . ? C25 C24 1.388(4) . ? C25 H25 0.98(2) . ? C23 C24 1.377(4) . ? C23 H23 0.99(3) . ? C19 H19 0.96(3) . ? C24 H24 0.97(3) . ? N4 C48 1.336(3) . ? N4 C52 1.339(3) . ? C50 C51 1.388(3) . ? C50 C49 1.394(3) . ? C50 C53 1.482(3) . ? C53 C54 1.394(3) . ? C53 C58 1.396(3) . ? C58 C57 1.384(3) . ? C58 H58 0.99(3) . ? C54 C55 1.380(3) . ? C54 H54 0.94(2) . ? C48 C49 1.382(3) . ? C48 H48 1.01(3) . ? C51 C52 1.376(3) . ? C51 H51 0.93(2) . ? C55 C56 1.380(3) . ? C55 H55 0.98(2) . ? C49 H49 0.96(2) . ? C57 C56 1.390(4) . ? C57 H57 0.97(3) . ? C56 H56 1.00(2) . ? C52 H52 0.99(2) . ? N2 C30 1.334(3) . ? N2 C26 1.337(3) . ? C31 C32 1.389(3) . ? C31 C36 1.395(3) . ? C31 C28 1.481(3) . ? C28 C27 1.388(3) . ? C28 C29 1.391(3) . ? C33 C34 1.374(4) . ? C33 C32 1.384(3) . ? C33 H33 1.00(3) . ? C32 H32 0.97(2) . ? C36 C35 1.388(4) . ? C36 H36 0.97(2) . ? C30 C29 1.378(3) . ? C30 H30 1.00(2) . ? C35 C34 1.385(4) . ? C35 H35 0.96(3) . ? C29 H29 0.97(2) . ? C34 H34 0.95(3) . ? C27 C26 1.378(4) . ? C27 H27 1.00(3) . ? C26 H26 0.97(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 C5 O3 H3O 116.2(18) . . ? C1 O1 H1O 110(2) . . ? C43 C42 C47 119.0(2) . . ? C43 C42 C39 121.0(2) . . ? C47 C42 C39 119.9(2) . . ? O3 C5 C4 122.3(2) . . ? O3 C5 C6 117.7(2) . . ? C4 C5 C6 120.0(2) . . ? C4 C3 C2 120.7(2) . . ? C4 C3 H3 120.8(13) . . ? C2 C3 H3 118.6(13) . . ? C37 N3 C41 117.2(2) . . ? C7 C2 C3 119.0(2) . . ? C7 C2 C1 122.2(2) . . ? C3 C2 C1 118.8(2) . . ? N3 C41 C40 122.7(2) . . ? N3 C41 H41 116.2(14) . . ? C40 C41 H41 121.2(14) . . ? O2 C1 O1 122.2(2) . . ? O2 C1 C2 123.1(2) . . ? O1 C1 C2 114.6(2) . . ? C46 C45 C44 120.1(2) . . ? C46 C45 H45 121.1(15) . . ? C44 C45 H45 118.7(15) . . ? C3 C4 C5 119.7(2) . . ? C3 C4 H4 121.5(12) . . ? C5 C4 H4 118.8(12) . . ? C44 C43 C42 120.5(2) . . ? C44 C43 H43 118.6(14) . . ? C42 C43 H43 120.9(14) . . ? C7 C6 C5 119.6(2) . . ? C7 C6 H6 119.0(14) . . ? C5 C6 H6 121.3(14) . . ? C6 C7 C2 121.0(2) . . ? C6 C7 H7 118.8(12) . . ? C2 C7 H7 120.2(12) . . ? C40 C39 C38 117.3(2) . . ? C40 C39 C42 120.8(2) . . ? C38 C39 C42 121.9(2) . . ? C45 C46 C47 120.6(2) . . ? C45 C46 H46 122.3(15) . . ? C47 C46 H46 117.1(15) . . ? C46 C47 C42 119.9(2) . . ? C46 C47 H47 119.7(13) . . ? C42 C47 H47 120.3(13) . . ? C37 C38 C39 119.0(3) . . ? C37 C38 H38 121.3(15) . . ? C39 C38 H38 119.6(15) . . ? C41 C40 C39 120.0(2) . . ? C41 C40 H40 119.4(14) . . ? C39 C40 H40 120.6(14) . . ? N3 C37 C38 123.8(2) . . ? N3 C37 H37 116.5(16) . . ? C38 C37 H37 119.6(16) . . ? C45 C44 C43 119.8(2) . . ? C45 C44 H44 119.7(16) . . ? C43 C44 H44 120.4(16) . . ? C8 O4 H4O 107.9(17) . . ? C12 O6 H6O 112.7(18) . . ? C11 C10 C9 120.9(2) . . ? C11 C10 H10 120.2(13) . . ? C9 C10 H10 118.9(13) . . ? O5 C8 O4 122.4(2) . . ? O5 C8 C9 122.84(19) . . ? O4 C8 C9 114.80(19) . . ? C10 C9 C14 118.8(2) . . ? C10 C9 C8 122.73(19) . . ? C14 C9 C8 118.48(19) . . ? C10 C11 C12 119.9(2) . . ? C10 C11 H11 120.2(13) . . ? C12 C11 H11 119.9(13) . . ? C13 C14 C9 120.7(2) . . ? C13 C14 H14 119.9(13) . . ? C9 C14 H14 119.4(13) . . ? C19 N1 C15 116.8(2) . . ? C16 C17 C18 117.1(2) . . ? C16 C17 C20 121.2(2) . . ? C18 C17 C20 121.6(2) . . ? O6 C12 C11 118.0(2) . . ? O6 C12 C13 122.4(2) . . ? C11 C12 C13 119.7(2) . . ? C19 C18 C17 119.2(2) . . ? C19 C18 H18 121.3(15) . . ? C17 C18 H18 119.5(15) . . ? C15 C16 C17 119.8(2) . . ? C15 C16 H16 118.8(15) . . ? C17 C16 H16 121.3(15) . . ? C14 C13 C12 120.0(2) . . ? C14 C13 H13 120.9(13) . . ? C12 C13 H13 119.1(13) . . ? C21 C20 C25 118.2(2) . . ? C21 C20 C17 120.8(2) . . ? C25 C20 C17 120.9(2) . . ? N1 C15 C16 123.2(2) . . ? N1 C15 H15 117.3(13) . . ? C16 C15 H15 119.4(13) . . ? C22 C21 C20 121.4(3) . . ? C22 C21 H21 120.6(14) . . ? C20 C21 H21 117.9(14) . . ? C23 C22 C21 119.7(3) . . ? C23 C22 H22 118.9(14) . . ? C21 C22 H22 121.3(14) . . ? C24 C25 C20 120.3(3) . . ? C24 C25 H25 119.2(14) . . ? C20 C25 H25 120.5(14) . . ? C24 C23 C22 120.0(3) . . ? C24 C23 H23 120.1(17) . . ? C22 C23 H23 119.8(17) . . ? N1 C19 C18 123.9(2) . . ? N1 C19 H19 118.0(15) . . ? C18 C19 H19 118.0(15) . . ? C23 C24 C25 120.3(3) . . ? C23 C24 H24 121.8(18) . . ? C25 C24 H24 117.8(18) . . ? C48 N4 C52 116.6(2) . . ? C51 C50 C49 116.4(2) . . ? C51 C50 C53 121.6(2) . . ? C49 C50 C53 121.9(2) . . ? C54 C53 C58 118.3(2) . . ? C54 C53 C50 120.4(2) . . ? C58 C53 C50 121.4(2) . . ? C57 C58 C53 120.5(2) . . ? C57 C58 H58 122.2(15) . . ? C53 C58 H58 117.3(14) . . ? C55 C54 C53 121.1(2) . . ? C55 C54 H54 121.1(14) . . ? C53 C54 H54 117.8(14) . . ? N4 C48 C49 123.3(2) . . ? N4 C48 H48 118.4(14) . . ? C49 C48 H48 118.3(14) . . ? C52 C51 C50 119.8(2) . . ? C52 C51 H51 119.6(15) . . ? C50 C51 H51 120.6(15) . . ? C54 C55 C56 120.4(2) . . ? C54 C55 H55 121.2(14) . . ? C56 C55 H55 118.4(14) . . ? C48 C49 C50 120.0(2) . . ? C48 C49 H49 120.3(14) . . ? C50 C49 H49 119.6(14) . . ? C58 C57 C56 120.5(2) . . ? C58 C57 H57 120.1(15) . . ? C56 C57 H57 119.3(15) . . ? C55 C56 C57 119.3(2) . . ? C55 C56 H56 119.8(14) . . ? C57 C56 H56 120.8(14) . . ? N4 C52 C51 123.9(2) . . ? N4 C52 H52 115.4(13) . . ? C51 C52 H52 120.6(13) . . ? C30 N2 C26 116.9(2) . . ? C32 C31 C36 118.4(2) . . ? C32 C31 C28 120.8(2) . . ? C36 C31 C28 120.7(2) . . ? C27 C28 C29 116.4(2) . . ? C27 C28 C31 122.5(2) . . ? C29 C28 C31 121.2(2) . . ? C34 C33 C32 120.3(2) . . ? C34 C33 H33 120.6(16) . . ? C32 C33 H33 119.2(16) . . ? C33 C32 C31 120.9(2) . . ? C33 C32 H32 119.4(14) . . ? C31 C32 H32 119.7(14) . . ? C35 C36 C31 120.5(2) . . ? C35 C36 H36 120.8(15) . . ? C31 C36 H36 118.6(15) . . ? N2 C30 C29 123.3(2) . . ? N2 C30 H30 113.8(13) . . ? C29 C30 H30 122.9(13) . . ? C34 C35 C36 120.0(2) . . ? C34 C35 H35 119.2(15) . . ? C36 C35 H35 120.7(15) . . ? C30 C29 C28 120.1(2) . . ? C30 C29 H29 120.1(15) . . ? C28 C29 H29 119.8(15) . . ? C33 C34 C35 119.9(2) . . ? C33 C34 H34 121.2(15) . . ? C35 C34 H34 118.9(15) . . ? C26 C27 C28 120.0(2) . . ? C26 C27 H27 119.6(15) . . ? C28 C27 H27 120.5(15) . . ? N2 C26 C27 123.4(2) . . ? N2 C26 H26 114.1(17) . . ? C27 C26 H26 122.4(17) . . ? 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 C4 C3 C2 C7 -0.7(3) . . . . ? C4 C3 C2 C1 -179.6(2) . . . . ? C37 N3 C41 C40 -0.6(4) . . . . ? C7 C2 C1 O2 -177.1(2) . . . . ? C3 C2 C1 O2 1.7(4) . . . . ? C7 C2 C1 O1 2.8(3) . . . . ? C3 C2 C1 O1 -178.4(2) . . . . ? C2 C3 C4 C5 0.5(3) . . . . ? O3 C5 C4 C3 180.0(2) . . . . ? C6 C5 C4 C3 0.3(3) . . . . ? C47 C42 C43 C44 0.7(3) . . . . ? C39 C42 C43 C44 -176.2(2) . . . . ? O3 C5 C6 C7 179.4(2) . . . . ? C4 C5 C6 C7 -0.9(3) . . . . ? C5 C6 C7 C2 0.6(3) . . . . ? C3 C2 C7 C6 0.1(3) . . . . ? C1 C2 C7 C6 179.0(2) . . . . ? C43 C42 C39 C40 135.3(2) . . . . ? C47 C42 C39 C40 -41.6(3) . . . . ? C43 C42 C39 C38 -43.7(3) . . . . ? C47 C42 C39 C38 139.4(2) . . . . ? C44 C45 C46 C47 0.3(4) . . . . ? C45 C46 C47 C42 0.2(4) . . . . ? C43 C42 C47 C46 -0.7(3) . . . . ? C39 C42 C47 C46 176.3(2) . . . . ? C40 C39 C38 C37 0.6(4) . . . . ? C42 C39 C38 C37 179.6(2) . . . . ? N3 C41 C40 C39 0.3(4) . . . . ? C38 C39 C40 C41 -0.3(4) . . . . ? C42 C39 C40 C41 -179.4(2) . . . . ? C41 N3 C37 C38 0.9(4) . . . . ? C39 C38 C37 N3 -0.9(4) . . . . ? C46 C45 C44 C43 -0.3(4) . . . . ? C42 C43 C44 C45 -0.3(4) . . . . ? C11 C10 C9 C14 0.5(3) . . . . ? C11 C10 C9 C8 -179.0(2) . . . . ? O5 C8 C9 C10 179.2(2) . . . . ? O4 C8 C9 C10 -1.2(3) . . . . ? O5 C8 C9 C14 -0.3(3) . . . . ? O4 C8 C9 C14 179.3(2) . . . . ? C9 C10 C11 C12 -0.2(3) . . . . ? C10 C9 C14 C13 -0.6(3) . . . . ? C8 C9 C14 C13 178.9(2) . . . . ? C10 C11 C12 O6 -179.6(2) . . . . ? C10 C11 C12 C13 0.0(3) . . . . ? C16 C17 C18 C19 1.0(3) . . . . ? C20 C17 C18 C19 -177.9(2) . . . . ? C18 C17 C16 C15 -1.3(3) . . . . ? C20 C17 C16 C15 177.6(2) . . . . ? C9 C14 C13 C12 0.4(3) . . . . ? O6 C12 C13 C14 179.5(2) . . . . ? C11 C12 C13 C14 -0.1(3) . . . . ? C16 C17 C20 C21 31.7(3) . . . . ? C18 C17 C20 C21 -149.5(2) . . . . ? C16 C17 C20 C25 -146.9(2) . . . . ? C18 C17 C20 C25 31.9(3) . . . . ? C19 N1 C15 C16 0.6(3) . . . . ? C17 C16 C15 N1 0.5(4) . . . . ? C25 C20 C21 C22 -0.4(4) . . . . ? C17 C20 C21 C22 -179.0(2) . . . . ? C20 C21 C22 C23 -0.2(4) . . . . ? C21 C20 C25 C24 0.2(4) . . . . ? C17 C20 C25 C24 178.8(2) . . . . ? C21 C22 C23 C24 1.0(4) . . . . ? C15 N1 C19 C18 -0.9(4) . . . . ? C17 C18 C19 N1 0.1(4) . . . . ? C22 C23 C24 C25 -1.1(4) . . . . ? C20 C25 C24 C23 0.5(4) . . . . ? C51 C50 C53 C54 -30.4(3) . . . . ? C49 C50 C53 C54 149.7(2) . . . . ? C51 C50 C53 C58 149.0(2) . . . . ? C49 C50 C53 C58 -30.9(3) . . . . ? C54 C53 C58 C57 -1.2(3) . . . . ? C50 C53 C58 C57 179.4(2) . . . . ? C58 C53 C54 C55 1.4(3) . . . . ? C50 C53 C54 C55 -179.2(2) . . . . ? C52 N4 C48 C49 1.1(3) . . . . ? C49 C50 C51 C52 0.8(3) . . . . ? C53 C50 C51 C52 -179.1(2) . . . . ? C53 C54 C55 C56 -0.5(4) . . . . ? N4 C48 C49 C50 -0.5(4) . . . . ? C51 C50 C49 C48 -0.5(3) . . . . ? C53 C50 C49 C48 179.4(2) . . . . ? C53 C58 C57 C56 0.2(4) . . . . ? C54 C55 C56 C57 -0.6(4) . . . . ? C58 C57 C56 C55 0.7(4) . . . . ? C48 N4 C52 C51 -0.8(4) . . . . ? C50 C51 C52 N4 -0.1(4) . . . . ? C32 C31 C28 C27 145.3(2) . . . . ? C36 C31 C28 C27 -38.0(3) . . . . ? C32 C31 C28 C29 -35.1(3) . . . . ? C36 C31 C28 C29 141.6(2) . . . . ? C34 C33 C32 C31 1.7(4) . . . . ? C36 C31 C32 C33 -1.4(3) . . . . ? C28 C31 C32 C33 175.4(2) . . . . ? C32 C31 C36 C35 0.6(3) . . . . ? C28 C31 C36 C35 -176.2(2) . . . . ? C26 N2 C30 C29 -0.5(4) . . . . ? C31 C36 C35 C34 0.0(4) . . . . ? N2 C30 C29 C28 -0.5(4) . . . . ? C27 C28 C29 C30 1.3(4) . . . . ? C31 C28 C29 C30 -178.3(2) . . . . ? C32 C33 C34 C35 -1.0(4) . . . . ? C36 C35 C34 C33 0.2(4) . . . . ? C29 C28 C27 C26 -1.1(4) . . . . ? C31 C28 C27 C26 178.5(2) . . . . ? C30 N2 C26 C27 0.6(4) . . . . ? C28 C27 C26 N2 0.1(5) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.205 _refine_diff_density_min -0.303 _refine_diff_density_rms 0.050