# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2008 data_global _journal_coden_Cambridge 440 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Kumar Biradha' 'Ramkinkar Santra' _publ_contact_author_name 'Kumar Biradha' _publ_contact_author_email KBIRADHA@CHEM.IITKGP.ERNET.IN _publ_section_title ; Crystal Engineering of Co-crystals with Acid and Pyridine Heteromeric Synthon: Neutral and Ionic Pseudo Polymorphs ; # Attachment 'kb.cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 682928' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H26 N2 O8' _chemical_formula_weight 518.51 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 C2/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 23.612(2) _cell_length_b 15.0618(12) _cell_length_c 17.8456(15) _cell_angle_alpha 90.00 _cell_angle_beta 128.492(2) _cell_angle_gamma 90.00 _cell_volume 4967.5(7) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6426 _cell_measurement_theta_min 1.74 _cell_measurement_theta_max 28.74 _exptl_crystal_description Needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.387 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2176 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.93 _exptl_absorpt_correction_T_max 0.95 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Bruker-APEX-2 CCD area detector' _diffrn_measurement_method hemisphere _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 35036 _diffrn_reflns_av_R_equivalents 0.0762 _diffrn_reflns_av_sigmaI/netI 0.0875 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 28.74 _reflns_number_total 6426 _reflns_number_gt 2963 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0708P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6426 _refine_ls_number_parameters 337 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1592 _refine_ls_R_factor_gt 0.0637 _refine_ls_wR_factor_ref 0.1565 _refine_ls_wR_factor_gt 0.1302 _refine_ls_goodness_of_fit_ref 0.942 _refine_ls_restrained_S_all 0.942 _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 O1A O 0.40487(10) 0.86757(12) 1.01782(18) 0.1019(9) Uani 1 1 d . . . C1A C 0.34221(13) 0.89105(16) 0.9615(2) 0.0585(7) Uani 1 1 d . . . C2A C 0.28200(11) 0.82557(14) 0.92186(16) 0.0421(6) Uani 1 1 d . . . C3A C 0.20980(12) 0.86102(14) 0.88699(17) 0.0449(6) Uani 1 1 d . . . H3A1 H 0.1928 0.8265 0.9154 0.054 Uiso 1 1 calc . . . H3A2 H 0.1753 0.8536 0.8181 0.054 Uiso 1 1 calc . . . C4A C 0.21250(13) 0.95823(15) 0.91122(19) 0.0550(7) Uani 1 1 d . . . H4A1 H 0.1637 0.9795 0.8801 0.066 Uiso 1 1 calc . . . H4A2 H 0.2398 0.9645 0.9798 0.066 Uiso 1 1 calc . . . C5A C 0.24728(12) 1.01414(14) 0.87940(18) 0.0493(6) Uani 1 1 d . . . H5A1 H 0.2186 1.0102 0.8104 0.059 Uiso 1 1 calc . . . H5A2 H 0.2479 1.0757 0.8957 0.059 Uiso 1 1 calc . . . C6A C 0.32278(11) 0.98484(14) 0.92515(17) 0.0456(6) Uani 1 1 d . . . N1B N 0.17494(12) 0.50313(13) 0.80166(16) 0.0610(6) Uani 1 1 d . . . C1B C 0.24456(15) 0.50761(16) 0.84055(19) 0.0588(7) Uani 1 1 d . . . H1B H 0.2670 0.4565 0.8412 0.071 Uiso 1 1 calc R . . C2B C 0.28502(13) 0.58364(15) 0.87978(17) 0.0491(6) Uani 1 1 d . . . H2B H 0.3337 0.5831 0.9066 0.059 Uiso 1 1 calc R . . C3B C 0.25332(12) 0.66115(14) 0.87946(16) 0.0419(6) Uani 1 1 d . . . C4B C 0.18084(12) 0.65612(15) 0.84031(18) 0.0535(7) Uani 1 1 d . . . H4B H 0.1572 0.7058 0.8397 0.064 Uiso 1 1 calc R . . C5B C 0.14455(14) 0.57740(17) 0.8026(2) 0.0622(8) Uani 1 1 d . . . H5B H 0.0960 0.5756 0.7762 0.075 Uiso 1 1 calc R . . C6B C 0.29839(12) 0.74121(14) 0.91894(18) 0.0488(6) Uani 1 1 d . . . H6B H 0.3468 0.7317 0.9468 0.059 Uiso 1 1 calc R . . N1C N 0.39440(9) 1.29903(12) 0.87437(13) 0.0435(5) Uani 1 1 d . . . C1C C 0.44985(12) 1.24317(15) 0.92213(17) 0.0498(7) Uani 1 1 d . . . H1C H 0.4949 1.2632 0.9435 0.060 Uiso 1 1 calc R . . C2C C 0.44366(12) 1.15715(15) 0.94147(18) 0.0516(7) Uani 1 1 d . . . H2C H 0.4842 1.1205 0.9752 0.062 Uiso 1 1 calc R . . C3C C 0.37754(11) 1.12425(14) 0.91113(16) 0.0428(6) Uani 1 1 d . . . C4C C 0.31943(11) 1.18280(14) 0.85894(16) 0.0424(6) Uani 1 1 d . . . H4C H 0.2734 1.1644 0.8353 0.051 Uiso 1 1 calc R . . C5C C 0.33031(12) 1.26775(14) 0.84252(16) 0.0430(6) Uani 1 1 d . . . H5C H 0.2906 1.3055 0.8071 0.052 Uiso 1 1 calc R . . C6C C 0.37535(12) 1.03307(15) 0.93688(19) 0.0550(7) Uani 1 1 d . . . H6C H 0.4188 1.0027 0.9673 0.066 Uiso 1 1 calc R . . O11 O 0.08477(8) -0.03572(11) 0.64610(12) 0.0566(5) Uani 1 1 d . . . O12 O -0.03020(9) -0.07279(11) 0.56615(15) 0.0760(6) Uani 1 1 d . . . O13 O -0.20423(8) 0.15756(11) 0.50714(13) 0.0609(5) Uani 1 1 d . . . O14 O -0.16428(9) 0.29369(11) 0.56397(13) 0.0608(5) Uani 1 1 d . . . O15 O 0.08072(9) 0.37427(12) 0.71171(14) 0.0713(6) Uani 1 1 d . . . O16 O 0.16453(9) 0.27581(12) 0.74951(15) 0.0782(6) Uani 1 1 d . . . C11 C 0.00396(11) 0.07616(14) 0.61839(16) 0.0388(5) Uani 1 1 d . . . C12 C -0.06506(11) 0.10063(14) 0.58315(16) 0.0412(6) Uani 1 1 d . . . H12 H -0.1019 0.0585 0.5535 0.049 Uiso 1 1 calc R . . C13 C -0.07975(11) 0.18724(14) 0.59173(16) 0.0386(5) Uani 1 1 d . . . C14 C -0.02527(11) 0.25017(14) 0.63568(16) 0.0403(6) Uani 1 1 d . . . H14 H -0.0350 0.3082 0.6422 0.048 Uiso 1 1 calc R . . C15 C 0.04389(11) 0.22661(14) 0.67007(16) 0.0387(5) Uani 1 1 d . . . C16 C 0.05842(11) 0.13962(14) 0.66190(16) 0.0418(6) Uani 1 1 d . . . H16 H 0.1050 0.1236 0.6857 0.050 Uiso 1 1 calc R . . C17 C 0.01758(12) -0.01835(15) 0.60737(17) 0.0460(6) Uani 1 1 d . . . C18 C -0.15438(12) 0.21369(15) 0.55177(17) 0.0430(6) Uani 1 1 d . . . C19 C 0.10293(12) 0.29389(16) 0.71466(18) 0.0502(6) Uani 1 1 d . . . H11O H 0.0902(16) -0.107(2) 0.639(2) 0.110(11) Uiso 1 1 d . . . H15O H 0.1184(19) 0.419(2) 0.746(2) 0.125(13) Uiso 1 1 d . . . H13O H -0.222(2) 0.315(3) 0.535(3) 0.162(15) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1A 0.0437(11) 0.0431(11) 0.156(2) 0.0319(12) 0.0311(12) 0.0011(9) C1A 0.0392(13) 0.0340(14) 0.085(2) 0.0121(13) 0.0302(14) -0.0005(11) C2A 0.0437(12) 0.0285(13) 0.0510(14) 0.0041(10) 0.0280(11) -0.0047(10) C3A 0.0515(14) 0.0302(13) 0.0625(16) -0.0021(11) 0.0401(13) -0.0048(10) C4A 0.0675(16) 0.0308(14) 0.086(2) -0.0011(13) 0.0571(16) -0.0045(12) C5A 0.0514(14) 0.0311(13) 0.0744(17) 0.0050(12) 0.0436(13) 0.0001(11) C6A 0.0389(12) 0.0280(12) 0.0602(15) 0.0056(11) 0.0261(11) -0.0025(10) N1B 0.0620(14) 0.0331(12) 0.0735(15) -0.0119(10) 0.0352(12) -0.0111(10) C1B 0.0687(18) 0.0340(15) 0.0709(19) -0.0035(13) 0.0421(15) 0.0025(13) C2B 0.0508(14) 0.0320(14) 0.0632(17) 0.0019(12) 0.0348(13) 0.0004(11) C3B 0.0463(13) 0.0274(12) 0.0520(14) 0.0043(10) 0.0305(11) -0.0011(10) C4B 0.0499(14) 0.0290(13) 0.0763(18) -0.0045(12) 0.0366(13) -0.0039(11) C5B 0.0536(15) 0.0393(16) 0.086(2) -0.0076(14) 0.0400(15) -0.0064(12) C6B 0.0399(12) 0.0297(13) 0.0688(17) 0.0084(11) 0.0299(12) -0.0005(10) N1C 0.0420(10) 0.0284(10) 0.0578(13) 0.0022(9) 0.0300(10) -0.0055(8) C1C 0.0389(13) 0.0380(14) 0.0664(17) 0.0036(12) 0.0297(12) -0.0104(11) C2C 0.0401(12) 0.0336(14) 0.0750(18) 0.0080(12) 0.0328(13) 0.0005(10) C3C 0.0360(12) 0.0282(12) 0.0599(15) 0.0007(11) 0.0277(11) -0.0047(10) C4C 0.0356(11) 0.0330(13) 0.0584(15) -0.0014(11) 0.0291(11) -0.0066(10) C5C 0.0423(12) 0.0281(12) 0.0568(15) -0.0009(11) 0.0300(12) -0.0039(10) C6C 0.0389(12) 0.0297(13) 0.0836(19) 0.0076(12) 0.0318(13) 0.0005(10) O11 0.0395(9) 0.0325(10) 0.0822(13) -0.0092(8) 0.0302(9) 0.0058(7) O12 0.0463(10) 0.0340(10) 0.1205(17) -0.0184(10) 0.0386(11) -0.0030(8) O13 0.0390(9) 0.0392(10) 0.0994(14) -0.0042(9) 0.0405(10) -0.0014(8) O14 0.0442(9) 0.0425(10) 0.0989(14) -0.0101(9) 0.0461(10) 0.0061(8) O15 0.0469(10) 0.0335(10) 0.1031(16) -0.0166(10) 0.0316(11) -0.0043(8) O16 0.0410(10) 0.0534(12) 0.1243(17) -0.0235(11) 0.0437(11) -0.0076(9) C11 0.0359(11) 0.0287(12) 0.0471(13) -0.0025(10) 0.0235(10) 0.0038(9) C12 0.0367(12) 0.0283(12) 0.0569(15) -0.0029(10) 0.0283(11) -0.0022(9) C13 0.0355(11) 0.0318(13) 0.0522(14) -0.0015(10) 0.0291(11) 0.0017(9) C14 0.0393(12) 0.0309(12) 0.0542(14) -0.0029(10) 0.0308(11) 0.0048(10) C15 0.0351(11) 0.0283(12) 0.0498(14) -0.0063(10) 0.0249(10) -0.0019(9) C16 0.0329(11) 0.0347(13) 0.0530(14) -0.0021(11) 0.0244(11) 0.0026(10) C17 0.0383(13) 0.0312(13) 0.0606(16) -0.0020(11) 0.0268(12) 0.0036(11) C18 0.0427(13) 0.0306(13) 0.0620(16) -0.0001(11) 0.0358(12) 0.0019(11) C19 0.0428(13) 0.0364(14) 0.0646(17) -0.0091(12) 0.0301(13) 0.0004(11) _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 O1A C1A 1.214(3) . ? C1A C2A 1.497(3) . ? C1A C6A 1.502(3) . ? C2A C6B 1.339(3) . ? C2A C3A 1.503(3) . ? C3A C4A 1.517(3) . ? C4A C5A 1.512(3) . ? C5A C6A 1.493(3) . ? C6A C6C 1.337(3) . ? N1B C1B 1.330(3) . ? N1B C5B 1.335(3) . ? C1B C2B 1.372(3) . ? C2B C3B 1.385(3) . ? C3B C4B 1.391(3) . ? C3B C6B 1.466(3) . ? C4B C5B 1.369(3) . ? N1C C1C 1.326(3) . ? N1C C5C 1.329(3) . ? C1C C2C 1.372(3) . ? C2C C3C 1.387(3) . ? C3C C4C 1.392(3) . ? C3C C6C 1.459(3) . ? C4C C5C 1.372(3) . ? O11 C17 1.303(2) . ? O12 C17 1.205(3) . ? O13 C18 1.252(3) . ? O14 C18 1.272(3) . ? O15 C19 1.307(3) . ? O16 C19 1.204(3) . ? C11 C12 1.383(3) . ? C11 C16 1.388(3) . ? C11 C17 1.499(3) . ? C12 C13 1.383(3) . ? C13 C14 1.383(3) . ? C13 C18 1.486(3) . ? C14 C15 1.386(3) . ? C15 C16 1.385(3) . ? C15 C19 1.491(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 O1A C1A C2A 120.6(2) . . ? O1A C1A C6A 121.2(2) . . ? C2A C1A C6A 118.06(19) . . ? C6B C2A C1A 115.5(2) . . ? C6B C2A C3A 127.0(2) . . ? C1A C2A C3A 117.40(19) . . ? C2A C3A C4A 112.92(18) . . ? C5A C4A C3A 111.5(2) . . ? C6A C5A C4A 111.9(2) . . ? C6C C6A C5A 127.0(2) . . ? C6C C6A C1A 116.0(2) . . ? C5A C6A C1A 116.99(18) . . ? C1B N1B C5B 116.8(2) . . ? N1B C1B C2B 123.4(2) . . ? C1B C2B C3B 119.9(2) . . ? C2B C3B C4B 116.7(2) . . ? C2B C3B C6B 117.6(2) . . ? C4B C3B C6B 125.8(2) . . ? C5B C4B C3B 119.5(2) . . ? N1B C5B C4B 123.7(2) . . ? C2A C6B C3B 131.2(2) . . ? C1C N1C C5C 117.12(19) . . ? N1C C1C C2C 122.9(2) . . ? C1C C2C C3C 120.6(2) . . ? C2C C3C C4C 115.9(2) . . ? C2C C3C C6C 117.72(19) . . ? C4C C3C C6C 126.42(19) . . ? C5C C4C C3C 119.7(2) . . ? N1C C5C C4C 123.7(2) . . ? C6A C6C C3C 132.3(2) . . ? C12 C11 C16 119.35(19) . . ? C12 C11 C17 118.81(19) . . ? C16 C11 C17 121.83(19) . . ? C13 C12 C11 120.47(19) . . ? C12 C13 C14 120.04(19) . . ? C12 C13 C18 120.26(19) . . ? C14 C13 C18 119.68(19) . . ? C13 C14 C15 120.0(2) . . ? C16 C15 C14 119.75(19) . . ? C16 C15 C19 119.25(19) . . ? C14 C15 C19 120.99(19) . . ? C15 C16 C11 120.42(19) . . ? O12 C17 O11 123.7(2) . . ? O12 C17 C11 122.0(2) . . ? O11 C17 C11 114.25(19) . . ? O13 C18 O14 123.3(2) . . ? O13 C18 C13 119.3(2) . . ? O14 C18 C13 117.5(2) . . ? O16 C19 O15 123.7(2) . . ? O16 C19 C15 123.3(2) . . ? O15 C19 C15 112.9(2) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 28.74 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.325 _refine_diff_density_min -0.245 _refine_diff_density_rms 0.042 data_3 _database_code_depnum_ccdc_archive 'CCDC 682929' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C54 H44 N4 O14' _chemical_formula_weight 972.83 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 P2(1)/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 19.1296(7) _cell_length_b 7.7639(3) _cell_length_c 15.7687(6) _cell_angle_alpha 90.00 _cell_angle_beta 98.1380(10) _cell_angle_gamma 90.00 _cell_volume 2318.39(15) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6721 _cell_measurement_theta_min 2.15 _cell_measurement_theta_max 30.13 _exptl_crystal_description 'square plates' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.394 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1016 _exptl_absorpt_coefficient_mu 0.102 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.89 _exptl_absorpt_correction_T_max 0.95 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Bruker-APEX-2 CCD area detector' _diffrn_measurement_method hemisphere _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 32922 _diffrn_reflns_av_R_equivalents 0.0363 _diffrn_reflns_av_sigmaI/netI 0.0340 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 30.13 _reflns_number_total 6721 _reflns_number_gt 3965 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6721 _refine_ls_number_parameters 335 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0964 _refine_ls_R_factor_gt 0.0504 _refine_ls_wR_factor_ref 0.1690 _refine_ls_wR_factor_gt 0.1396 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _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 C11 C 0.21738(7) 0.29869(19) 0.46251(9) 0.0415(3) Uani 1 1 d . . . C12 C 0.27472(7) 0.2192(2) 0.43350(9) 0.0418(3) Uani 1 1 d . . . H12 H 0.2703 0.1755 0.3781 0.050 Uiso 1 1 calc R . . C13 C 0.33861(7) 0.2048(2) 0.48720(9) 0.0403(3) Uani 1 1 d . . . C14 C 0.34489(7) 0.2746(2) 0.56909(9) 0.0422(3) Uani 1 1 d . . . H14 H 0.3878 0.2670 0.6049 0.051 Uiso 1 1 calc R . . C15 C 0.28815(7) 0.35517(19) 0.59830(9) 0.0415(3) Uani 1 1 d . . . C16 C 0.22420(7) 0.3665(2) 0.54454(9) 0.0426(3) Uani 1 1 d . . . H16 H 0.1858 0.4198 0.5637 0.051 Uiso 1 1 calc R . . C17 C 0.14654(8) 0.3053(2) 0.40770(10) 0.0476(4) Uani 1 1 d . . . C18 C 0.39957(7) 0.1078(2) 0.46027(9) 0.0446(4) Uani 1 1 d . . . C19 C 0.29403(8) 0.4186(2) 0.68810(10) 0.0480(4) Uani 1 1 d . . . N1A N -0.46989(7) 0.47937(19) -0.41864(9) 0.0563(4) Uani 1 1 d . . . C1A C -0.49294(9) 0.5390(3) -0.34860(12) 0.0676(5) Uani 1 1 d . . . H1A H -0.5344 0.6033 -0.3547 0.081 Uiso 1 1 calc R . . C2A C -0.45832(8) 0.5098(3) -0.26814(11) 0.0623(5) Uani 1 1 d . . . H2A H -0.4765 0.5522 -0.2206 0.075 Uiso 1 1 calc R . . C3A C -0.39560(7) 0.4162(2) -0.25755(10) 0.0459(4) Uani 1 1 d . . . C4A C -0.37372(9) 0.3512(3) -0.33114(11) 0.0593(5) Uani 1 1 d . . . H4A H -0.3330 0.2847 -0.3273 0.071 Uiso 1 1 calc R . . C5A C -0.41175(9) 0.3844(3) -0.40963(11) 0.0624(5) Uani 1 1 d . . . H5A H -0.3963 0.3388 -0.4582 0.075 Uiso 1 1 calc R . . C6A C -0.35802(8) 0.3852(2) -0.17181(10) 0.0469(4) Uani 1 1 d . . . H6A H -0.3858 0.3723 -0.1283 0.056 Uiso 1 1 calc R . . N1B N 0.02989(7) 0.27638(19) 0.22178(9) 0.0534(4) Uani 1 1 d . . . C1B C 0.02379(9) 0.2287(2) 0.13979(12) 0.0570(4) Uani 1 1 d . . . H1B H 0.0638 0.1876 0.1192 0.068 Uiso 1 1 calc R . . C2B C -0.03820(8) 0.2369(2) 0.08398(11) 0.0529(4) Uani 1 1 d . . . H2B H -0.0398 0.2004 0.0276 0.063 Uiso 1 1 calc R . . C3B C -0.09857(8) 0.3007(2) 0.11313(10) 0.0455(4) Uani 1 1 d . . . C4B C -0.09195(8) 0.3508(2) 0.19871(11) 0.0529(4) Uani 1 1 d . . . H4B H -0.1308 0.3940 0.2212 0.064 Uiso 1 1 calc R . . C5B C -0.02759(9) 0.3361(2) 0.24998(11) 0.0552(4) Uani 1 1 d . . . H5B H -0.0243 0.3696 0.3070 0.066 Uiso 1 1 calc R . . C6B C -0.16850(8) 0.3115(2) 0.06105(11) 0.0494(4) Uani 1 1 d . . . H6B H -0.2065 0.3044 0.0917 0.059 Uiso 1 1 calc R . . O1C O -0.30623(6) 0.2981(2) -0.00844(8) 0.0704(4) Uani 1 1 d . . . C1C C -0.26356(7) 0.3315(2) -0.05617(10) 0.0459(4) Uani 1 1 d . . . C2C C -0.28774(7) 0.3730(2) -0.14840(10) 0.0435(3) Uani 1 1 d . . . C3C C -0.23345(8) 0.4039(2) -0.20724(10) 0.0520(4) Uani 1 1 d . . . H3C1 H -0.2521 0.4858 -0.2512 0.062 Uiso 1 1 calc . . . H3C2 H -0.2243 0.2967 -0.2353 0.062 Uiso 1 1 calc . . . C4C C -0.16485(8) 0.4725(2) -0.15952(11) 0.0555(4) Uani 1 1 d . . . H4C1 H -0.1729 0.5856 -0.1366 0.067 Uiso 1 1 calc . . . H4C2 H -0.1306 0.4847 -0.1990 0.067 Uiso 1 1 calc . . . C5C C -0.13527(8) 0.3538(2) -0.08693(11) 0.0554(4) Uani 1 1 d . . . H5C1 H -0.1250 0.2425 -0.1103 0.067 Uiso 1 1 calc . . . H5C2 H -0.0913 0.4012 -0.0581 0.067 Uiso 1 1 calc . . . C6C C -0.18564(7) 0.3300(2) -0.02308(10) 0.0445(4) Uani 1 1 d . . . O11 O 0.09308(6) 0.3408(2) 0.43586(9) 0.0758(4) Uani 1 1 d . . . O12 O 0.15011(6) 0.26777(19) 0.32767(8) 0.0644(4) Uani 1 1 d . . . O13 O 0.39808(6) 0.05173(18) 0.38747(7) 0.0616(4) Uani 1 1 d . . . O14 O 0.45168(5) 0.08669(18) 0.51977(7) 0.0617(4) Uani 1 1 d . . . O15 O 0.24669(7) 0.48434(18) 0.71848(8) 0.0651(4) Uani 1 1 d . . . O16 O 0.35740(7) 0.3941(2) 0.73008(8) 0.0805(5) Uani 1 1 d . . . H12O H 0.1018(14) 0.262(3) 0.2903(17) 0.106(8) Uiso 1 1 d . . . H16O H 0.3666(13) 0.425(3) 0.7928(18) 0.109(8) Uiso 1 1 d . . . H1N H -0.5000 0.5000 -0.5000 0.119(12) Uiso 1 2 d S . . H14O H 0.5000 0.0000 0.5000 0.125(13) Uiso 1 2 d S . . 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 C11 0.0311(7) 0.0506(8) 0.0405(8) 0.0069(6) -0.0027(6) 0.0041(6) C12 0.0348(7) 0.0562(9) 0.0324(7) 0.0027(6) -0.0023(5) 0.0043(6) C13 0.0325(7) 0.0548(9) 0.0319(7) 0.0033(6) -0.0013(5) 0.0061(6) C14 0.0329(7) 0.0577(9) 0.0338(7) 0.0013(6) -0.0028(5) 0.0052(6) C15 0.0392(7) 0.0498(8) 0.0345(7) 0.0024(6) 0.0019(6) 0.0033(6) C16 0.0354(7) 0.0501(8) 0.0421(8) 0.0049(6) 0.0045(6) 0.0075(6) C17 0.0331(7) 0.0608(10) 0.0459(9) 0.0077(7) -0.0046(6) 0.0050(6) C18 0.0333(7) 0.0680(10) 0.0305(7) 0.0026(7) -0.0018(5) 0.0072(6) C19 0.0451(8) 0.0599(10) 0.0387(8) -0.0019(7) 0.0054(6) 0.0024(7) N1A 0.0412(7) 0.0785(10) 0.0459(8) -0.0027(7) -0.0053(6) 0.0071(6) C1A 0.0424(9) 0.0963(15) 0.0597(11) -0.0110(10) -0.0081(8) 0.0228(9) C2A 0.0393(8) 0.0947(14) 0.0509(10) -0.0153(9) -0.0004(7) 0.0148(8) C3A 0.0327(7) 0.0575(10) 0.0453(8) -0.0043(7) -0.0023(6) -0.0015(6) C4A 0.0437(9) 0.0811(12) 0.0495(9) -0.0108(9) -0.0052(7) 0.0186(8) C5A 0.0479(9) 0.0922(13) 0.0445(9) -0.0136(9) -0.0031(7) 0.0147(9) C6A 0.0373(7) 0.0601(10) 0.0420(8) -0.0044(7) 0.0015(6) -0.0021(7) N1B 0.0376(7) 0.0693(9) 0.0496(8) 0.0081(7) -0.0067(6) -0.0028(6) C1B 0.0349(8) 0.0765(12) 0.0578(11) 0.0027(9) 0.0006(7) 0.0068(7) C2B 0.0409(8) 0.0712(11) 0.0448(9) -0.0020(8) -0.0004(7) 0.0042(7) C3B 0.0347(7) 0.0557(9) 0.0438(8) 0.0070(7) -0.0022(6) -0.0023(6) C4B 0.0386(8) 0.0733(11) 0.0464(9) 0.0057(8) 0.0044(7) 0.0014(7) C5B 0.0486(9) 0.0743(12) 0.0399(8) 0.0045(8) -0.0039(7) -0.0056(8) C6B 0.0321(7) 0.0675(10) 0.0475(9) 0.0043(7) 0.0020(6) -0.0004(7) O1C 0.0354(6) 0.1212(12) 0.0543(7) 0.0236(7) 0.0049(5) -0.0040(6) C1C 0.0315(7) 0.0585(9) 0.0467(9) 0.0049(7) 0.0021(6) -0.0007(6) C2C 0.0353(7) 0.0522(9) 0.0417(8) -0.0014(6) 0.0003(6) -0.0015(6) C3C 0.0399(8) 0.0695(11) 0.0458(9) 0.0076(8) 0.0032(6) -0.0005(7) C4C 0.0411(8) 0.0718(11) 0.0539(10) 0.0093(8) 0.0075(7) -0.0084(7) C5C 0.0331(7) 0.0810(12) 0.0515(10) 0.0065(8) 0.0037(7) -0.0026(7) C6C 0.0327(7) 0.0552(9) 0.0439(8) 0.0036(7) -0.0003(6) -0.0002(6) O11 0.0361(6) 0.1224(12) 0.0662(9) -0.0063(8) -0.0021(6) 0.0195(7) O12 0.0374(6) 0.1076(11) 0.0436(7) 0.0021(6) -0.0097(5) 0.0081(6) O13 0.0539(7) 0.0981(10) 0.0308(6) -0.0050(6) -0.0012(5) 0.0249(6) O14 0.0352(6) 0.1072(10) 0.0392(6) -0.0112(6) -0.0070(4) 0.0242(6) O15 0.0611(7) 0.0854(9) 0.0504(7) -0.0108(6) 0.0137(6) 0.0134(6) O16 0.0559(7) 0.1434(14) 0.0384(7) -0.0258(8) -0.0066(6) 0.0218(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 C11 C16 1.385(2) . ? C11 C12 1.391(2) . ? C11 C17 1.5014(18) . ? C12 C13 1.3893(18) . ? C13 C14 1.390(2) . ? C13 C18 1.500(2) . ? C14 C15 1.387(2) . ? C15 C16 1.3889(19) . ? C15 C19 1.488(2) . ? C17 O11 1.2032(19) . ? C17 O12 1.306(2) . ? C18 O13 1.2242(18) . ? C18 O14 1.2791(16) . ? C19 O15 1.1971(19) . ? C19 O16 1.3103(19) . ? N1A C5A 1.325(2) . ? N1A C1A 1.329(2) . ? C1A C2A 1.364(3) . ? C2A C3A 1.392(2) . ? C3A C4A 1.383(2) . ? C3A C6A 1.459(2) . ? C4A C5A 1.368(2) . ? C6A C2C 1.346(2) . ? N1B C5B 1.327(2) . ? N1B C1B 1.334(2) . ? C1B C2B 1.374(2) . ? C2B C3B 1.393(2) . ? C3B C4B 1.393(2) . ? C3B C6B 1.470(2) . ? C4B C5B 1.379(2) . ? C6B C6C 1.329(2) . ? O1C C1C 1.2139(19) . ? C1C C2C 1.497(2) . ? C1C C6C 1.5080(19) . ? C2C C3C 1.507(2) . ? C3C C4C 1.514(2) . ? C4C C5C 1.515(2) . ? C5C C6C 1.500(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C16 C11 C12 120.08(13) . . ? C16 C11 C17 118.85(13) . . ? C12 C11 C17 121.01(14) . . ? C13 C12 C11 120.10(14) . . ? C12 C13 C14 119.22(13) . . ? C12 C13 C18 121.33(13) . . ? C14 C13 C18 119.37(12) . . ? C15 C14 C13 121.03(13) . . ? C14 C15 C16 119.27(13) . . ? C14 C15 C19 120.53(13) . . ? C16 C15 C19 120.08(13) . . ? C11 C16 C15 120.28(13) . . ? O11 C17 O12 124.82(14) . . ? O11 C17 C11 122.71(15) . . ? O12 C17 C11 112.46(13) . . ? O13 C18 O14 123.69(14) . . ? O13 C18 C13 121.89(12) . . ? O14 C18 C13 114.40(13) . . ? O15 C19 O16 123.92(15) . . ? O15 C19 C15 124.21(14) . . ? O16 C19 C15 111.87(13) . . ? C5A N1A C1A 118.48(15) . . ? N1A C1A C2A 122.70(16) . . ? C1A C2A C3A 119.67(16) . . ? C4A C3A C2A 116.58(15) . . ? C4A C3A C6A 123.33(14) . . ? C2A C3A C6A 120.04(15) . . ? C5A C4A C3A 120.33(15) . . ? N1A C5A C4A 122.17(16) . . ? C2C C6A C3A 127.43(15) . . ? C5B N1B C1B 117.31(14) . . ? N1B C1B C2B 123.84(16) . . ? C1B C2B C3B 119.05(16) . . ? C4B C3B C2B 116.95(14) . . ? C4B C3B C6B 118.42(14) . . ? C2B C3B C6B 124.58(15) . . ? C5B C4B C3B 119.74(16) . . ? N1B C5B C4B 123.10(16) . . ? C6C C6B C3B 129.84(15) . . ? O1C C1C C2C 120.38(13) . . ? O1C C1C C6C 120.15(14) . . ? C2C C1C C6C 119.47(13) . . ? C6A C2C C1C 116.14(14) . . ? C6A C2C C3C 124.66(14) . . ? C1C C2C C3C 119.16(12) . . ? C2C C3C C4C 112.00(13) . . ? C3C C4C C5C 111.47(14) . . ? C6C C5C C4C 112.03(13) . . ? C6B C6C C5C 126.32(13) . . ? C6B C6C C1C 116.01(14) . . ? C5C C6C C1C 117.65(13) . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 30.13 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.267 _refine_diff_density_min -0.204 _refine_diff_density_rms 0.040 data_4 _database_code_depnum_ccdc_archive 'CCDC 682930' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C45 H38 N4 O8' _chemical_formula_weight 762.79 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 P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.6119(8) _cell_length_b 19.013(2) _cell_length_c 30.150(4) _cell_angle_alpha 90.00 _cell_angle_beta 92.300(4) _cell_angle_gamma 90.00 _cell_volume 3787.2(8) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 8612 _cell_measurement_theta_min 1.27 _cell_measurement_theta_max 27.50 _exptl_crystal_description needled _exptl_crystal_colour yellow _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.338 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1600 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.90 _exptl_absorpt_correction_T_max 0.98 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'Bruker-APEX-2 CCD area detector' _diffrn_measurement_method hemisphere _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 51218 _diffrn_reflns_av_R_equivalents 0.0389 _diffrn_reflns_av_sigmaI/netI 0.0287 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 1.27 _diffrn_reflns_theta_max 27.50 _reflns_number_total 8612 _reflns_number_gt 5851 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8612 _refine_ls_number_parameters 526 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0820 _refine_ls_R_factor_gt 0.0507 _refine_ls_wR_factor_ref 0.1718 _refine_ls_wR_factor_gt 0.1526 _refine_ls_goodness_of_fit_ref 1.104 _refine_ls_restrained_S_all 1.104 _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 O11 O 0.7462(2) 0.78606(8) 0.17270(6) 0.0795(5) Uani 1 1 d . . . O12 O 1.0114(2) 0.79459(7) 0.13072(5) 0.0682(4) Uani 1 1 d . . . O13 O 1.1520(2) 1.00069(6) 0.04510(5) 0.0631(4) Uani 1 1 d . . . O14 O 0.9452(2) 1.09345(6) 0.04640(5) 0.0585(4) Uani 1 1 d . . . O15 O 0.3280(2) 1.08458(7) 0.13346(5) 0.0669(4) Uani 1 1 d . . . O16 O 0.2629(2) 0.98674(7) 0.17091(5) 0.0595(4) Uani 1 1 d . . . C11 C 0.7845(3) 0.88959(8) 0.12972(6) 0.0443(4) Uani 1 1 d . . . C12 C 0.9095(3) 0.92586(8) 0.10213(6) 0.0454(4) Uani 1 1 d . . . H12 H 1.0295 0.9053 0.0936 0.054 Uiso 1 1 calc R . . C13 C 0.8580(3) 0.99282(8) 0.08693(6) 0.0438(4) Uani 1 1 d . . . C14 C 0.6795(3) 1.02341(9) 0.09999(6) 0.0455(4) Uani 1 1 d . . . H14 H 0.6443 1.0682 0.0900 0.055 Uiso 1 1 calc R . . C15 C 0.5530(3) 0.98734(8) 0.12789(6) 0.0448(4) Uani 1 1 d . . . C16 C 0.6052(3) 0.92038(9) 0.14238(6) 0.0473(4) Uani 1 1 d . . . H16 H 0.5197 0.8959 0.1607 0.057 Uiso 1 1 calc R . . C17 C 0.8429(3) 0.81826(9) 0.14682(7) 0.0511(4) Uani 1 1 d . . . C18 C 1.0004(3) 1.02872(9) 0.05736(6) 0.0481(4) Uani 1 1 d . . . C19 C 0.3701(3) 1.02479(9) 0.14356(6) 0.0491(4) Uani 1 1 d . . . N11A N 0.9566(2) 0.06355(7) 0.20145(5) 0.0526(4) Uani 1 1 d . . . C11A C 0.7982(3) 0.17696(9) 0.20552(6) 0.0472(4) Uani 1 1 d . . . C12A C 0.9557(3) 0.13280(9) 0.19406(7) 0.0512(4) Uani 1 1 d . . . H12A H 1.0661 0.1526 0.1805 0.061 Uiso 1 1 calc R . . C13A C 0.7977(3) 0.03542(10) 0.22056(6) 0.0523(5) Uani 1 1 d . . . H13A H 0.7990 -0.0125 0.2267 0.063 Uiso 1 1 calc R . . C14A C 0.6316(3) 0.07425(10) 0.23165(7) 0.0551(5) Uani 1 1 d . . . H14A H 0.5211 0.0528 0.2442 0.066 Uiso 1 1 calc R . . C15A C 0.6322(3) 0.14521(10) 0.22384(7) 0.0538(5) Uani 1 1 d . . . H15A H 0.5208 0.1722 0.2309 0.065 Uiso 1 1 calc R . . N21A N 1.1699(2) 0.67487(7) 0.15986(6) 0.0542(4) Uani 1 1 d . . . C21A C 1.1779(3) 0.54976(8) 0.17338(6) 0.0428(4) Uani 1 1 d . . . C22A C 1.0808(3) 0.61243(9) 0.16128(7) 0.0500(4) Uani 1 1 d . . . H22A H 0.9433 0.6103 0.1536 0.060 Uiso 1 1 calc R . . C23A C 1.3676(3) 0.67767(10) 0.17023(7) 0.0548(5) Uani 1 1 d . . . H23A H 1.4324 0.7211 0.1699 0.066 Uiso 1 1 calc R . . C24A C 1.4787(3) 0.61932(10) 0.18132(7) 0.0581(5) Uani 1 1 d . . . H24A H 1.6167 0.6233 0.1882 0.070 Uiso 1 1 calc R . . C25A C 1.3862(3) 0.55472(9) 0.18234(7) 0.0518(5) Uani 1 1 d . . . H25A H 1.4617 0.5145 0.1890 0.062 Uiso 1 1 calc R . . O31A O 0.7434(2) 0.39311(8) 0.18065(7) 0.0883(6) Uani 1 1 d . . . C31A C 0.9135(3) 0.37353(9) 0.19214(7) 0.0531(5) Uani 1 1 d . . . C32A C 0.9565(3) 0.29759(9) 0.20262(6) 0.0468(4) Uani 1 1 d . . . C33A C 1.1661(3) 0.27927(9) 0.21908(7) 0.0533(5) Uani 1 1 d . . . H33A H 1.2504 0.2711 0.1940 0.064 Uiso 1 1 calc . . . H33B H 1.1626 0.2362 0.2363 0.064 Uiso 1 1 calc . . . C34A C 1.2570(3) 0.33772(10) 0.24756(7) 0.0606(5) Uani 1 1 d . . . H34A H 1.3891 0.3234 0.2595 0.073 Uiso 1 1 calc . . . H34B H 1.1712 0.3469 0.2723 0.073 Uiso 1 1 calc . . . C35A C 1.2776(3) 0.40407(9) 0.22022(7) 0.0526(5) Uani 1 1 d . . . H35A H 1.3204 0.4423 0.2397 0.063 Uiso 1 1 calc . . . H35B H 1.3825 0.3970 0.1991 0.063 Uiso 1 1 calc . . . C36A C 1.0853(3) 0.42510(8) 0.19542(6) 0.0444(4) Uani 1 1 d . . . C37A C 0.8002(3) 0.25335(9) 0.19796(7) 0.0530(5) Uani 1 1 d . . . H37A H 0.6772 0.2734 0.1888 0.064 Uiso 1 1 calc R . . C38A C 1.0508(3) 0.48713(8) 0.17542(6) 0.0468(4) Uani 1 1 d . . . H38A H 0.9257 0.4909 0.1604 0.056 Uiso 1 1 calc R . . O31B O 1.2644(2) 1.44974(7) -0.08946(6) 0.0803(5) Uani 1 1 d . . . N11B N 1.9407(4) 1.69599(12) -0.08960(7) 0.0955(7) Uani 1 1 d . . . C11B C 1.6326(4) 1.62720(10) -0.08843(7) 0.0628(6) Uani 1 1 d . . . C12B C 1.8433(4) 1.63465(13) -0.08722(8) 0.0773(7) Uani 1 1 d . . . H12B H 1.9210 1.5940 -0.0846 0.093 Uiso 1 1 calc R . . C13B C 1.8258(6) 1.75301(15) -0.09305(9) 0.1008(11) Uani 1 1 d . . . H13B H 1.8905 1.7964 -0.0941 0.121 Uiso 1 1 calc R . . C14B C 1.6202(6) 1.75254(12) -0.09518(9) 0.0970(9) Uani 1 1 d . . . H14B H 1.5477 1.7943 -0.0980 0.116 Uiso 1 1 calc R . . C15B C 1.5203(5) 1.68831(11) -0.09303(8) 0.0804(7) Uani 1 1 d . . . H15B H 1.3796 1.6865 -0.0947 0.096 Uiso 1 1 calc R . . N21B N 1.2269(3) 1.14969(7) -0.00291(5) 0.0555(4) Uani 1 1 d . . . C21B C 1.3733(3) 1.24515(8) -0.04271(6) 0.0469(4) Uani 1 1 d . . . C22B C 1.2180(3) 1.21449(9) -0.01990(6) 0.0521(4) Uani 1 1 d . . . H22B H 1.1009 1.2406 -0.0162 0.062 Uiso 1 1 calc R . . C23B C 1.3946(3) 1.11212(10) -0.00903(7) 0.0592(5) Uani 1 1 d . . . H23B H 1.4039 1.0672 0.0032 0.071 Uiso 1 1 calc R . . C24B C 1.5528(3) 1.13671(10) -0.03236(7) 0.0610(5) Uani 1 1 d . . . H24B H 1.6658 1.1087 -0.0365 0.073 Uiso 1 1 calc R . . C25B C 1.5422(3) 1.20370(10) -0.04973(7) 0.0553(5) Uani 1 1 d . . . H25B H 1.6475 1.2211 -0.0661 0.066 Uiso 1 1 calc R . . C31B C 1.4337(3) 1.43955(9) -0.07334(7) 0.0498(4) Uani 1 1 d . . . C32B C 1.5855(3) 1.49786(9) -0.06960(6) 0.0491(4) Uani 1 1 d . . . C33B C 1.7859(3) 1.48403(11) -0.04690(8) 0.0658(6) Uani 1 1 d . . . H33C H 1.8267 1.5254 -0.0299 0.079 Uiso 1 1 calc . . . H33D H 1.8853 1.4765 -0.0692 0.079 Uiso 1 1 calc . . . C34B C 1.7874(3) 1.42151(12) -0.01624(8) 0.0704(6) Uani 1 1 d . . . H34C H 1.9246 1.4129 -0.0049 0.085 Uiso 1 1 calc . . . H34D H 1.7045 1.4316 0.0088 0.085 Uiso 1 1 calc . . . C35B C 1.7080(3) 1.35693(10) -0.03974(7) 0.0578(5) Uani 1 1 d . . . H35C H 1.7127 1.3174 -0.0194 0.069 Uiso 1 1 calc . . . H35D H 1.7935 1.3459 -0.0642 0.069 Uiso 1 1 calc . . . C36B C 1.4941(3) 1.36773(9) -0.05717(6) 0.0445(4) Uani 1 1 d . . . C37B C 1.5270(3) 1.55993(9) -0.08662(7) 0.0575(5) Uani 1 1 d . . . H37B H 1.3968 1.5603 -0.0995 0.069 Uiso 1 1 calc R . . C38B C 1.3509(3) 1.31825(9) -0.05756(6) 0.0494(4) Uani 1 1 d . . . H38B H 1.2230 1.3316 -0.0684 0.059 Uiso 1 1 calc R . . H16O H 0.147(4) 1.0159(12) 0.1782(8) 0.089(8) Uiso 1 1 d . . . H14O H 1.049(4) 1.1120(12) 0.0252(9) 0.092(8) Uiso 1 1 d . . . H12O H 1.060(4) 0.7493(13) 0.1394(8) 0.101(9) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O11 0.0677(10) 0.0559(8) 0.1165(13) 0.0355(8) 0.0227(9) 0.0030(7) O12 0.0646(9) 0.0440(7) 0.0974(11) 0.0226(7) 0.0187(8) 0.0155(6) O13 0.0648(9) 0.0465(7) 0.0795(10) 0.0127(6) 0.0212(8) 0.0116(6) O14 0.0654(9) 0.0385(6) 0.0723(9) 0.0131(6) 0.0133(7) 0.0093(6) O15 0.0681(9) 0.0466(7) 0.0870(11) 0.0073(7) 0.0157(8) 0.0183(6) O16 0.0503(8) 0.0464(7) 0.0827(10) 0.0022(6) 0.0123(7) 0.0045(6) C11 0.0458(10) 0.0329(8) 0.0536(11) 0.0012(7) -0.0043(8) -0.0017(7) C12 0.0448(10) 0.0384(8) 0.0527(11) -0.0001(7) -0.0007(8) 0.0030(7) C13 0.0497(10) 0.0343(8) 0.0471(10) 0.0013(7) -0.0016(8) 0.0010(7) C14 0.0496(10) 0.0350(8) 0.0514(10) -0.0002(7) -0.0045(8) 0.0043(7) C15 0.0434(9) 0.0385(8) 0.0521(10) -0.0048(7) -0.0037(8) 0.0013(7) C16 0.0468(10) 0.0404(9) 0.0545(11) -0.0014(7) 0.0004(8) -0.0040(7) C17 0.0466(10) 0.0386(9) 0.0677(12) 0.0076(8) -0.0028(9) -0.0043(8) C18 0.0532(11) 0.0372(8) 0.0538(11) 0.0022(7) 0.0005(9) 0.0036(8) C19 0.0449(10) 0.0436(9) 0.0587(11) -0.0040(8) -0.0012(8) 0.0007(8) N11A 0.0532(9) 0.0430(8) 0.0617(10) -0.0046(7) 0.0037(8) 0.0024(7) C11A 0.0433(10) 0.0428(9) 0.0556(11) 0.0019(8) 0.0036(8) 0.0003(7) C12A 0.0469(10) 0.0453(9) 0.0620(12) -0.0001(8) 0.0090(9) 0.0001(8) C13A 0.0591(12) 0.0429(9) 0.0544(11) -0.0009(8) -0.0036(9) -0.0053(8) C14A 0.0520(11) 0.0540(10) 0.0597(12) 0.0006(9) 0.0068(9) -0.0119(9) C15A 0.0416(10) 0.0527(10) 0.0675(13) 0.0010(9) 0.0065(9) 0.0008(8) N21A 0.0506(9) 0.0428(8) 0.0695(11) 0.0098(7) 0.0064(8) 0.0016(7) C21A 0.0409(9) 0.0417(9) 0.0462(10) 0.0025(7) 0.0038(7) 0.0056(7) C22A 0.0405(10) 0.0431(9) 0.0665(12) 0.0090(8) 0.0020(8) 0.0040(7) C23A 0.0551(12) 0.0500(10) 0.0594(12) 0.0037(9) 0.0048(9) -0.0081(9) C24A 0.0429(10) 0.0650(12) 0.0661(13) 0.0096(10) -0.0026(9) -0.0072(9) C25A 0.0428(10) 0.0513(10) 0.0613(12) 0.0103(8) 0.0003(8) 0.0079(8) O31A 0.0406(8) 0.0545(8) 0.1688(18) 0.0287(9) -0.0063(9) 0.0051(6) C31A 0.0381(10) 0.0438(9) 0.0778(13) 0.0084(9) 0.0070(9) 0.0091(7) C32A 0.0445(10) 0.0404(9) 0.0560(11) 0.0035(7) 0.0092(8) 0.0066(7) C33A 0.0506(11) 0.0422(9) 0.0670(12) 0.0057(8) -0.0011(9) 0.0082(8) C34A 0.0707(13) 0.0507(10) 0.0590(12) 0.0070(9) -0.0127(10) 0.0051(9) C35A 0.0517(11) 0.0443(9) 0.0609(12) 0.0045(8) -0.0084(9) 0.0023(8) C36A 0.0408(9) 0.0398(8) 0.0528(10) 0.0008(7) 0.0055(8) 0.0069(7) C37A 0.0425(10) 0.0444(10) 0.0725(13) 0.0077(9) 0.0059(9) 0.0074(8) C38A 0.0385(9) 0.0422(9) 0.0595(11) 0.0013(8) -0.0012(8) 0.0060(7) O31B 0.0538(9) 0.0525(8) 0.1325(15) 0.0241(9) -0.0234(9) -0.0056(6) N11B 0.128(2) 0.0781(15) 0.0819(15) -0.0045(11) 0.0180(14) -0.0488(14) C11B 0.0893(16) 0.0478(10) 0.0516(12) -0.0010(9) 0.0049(11) -0.0144(10) C12B 0.0950(19) 0.0697(14) 0.0681(15) -0.0038(11) 0.0140(13) -0.0316(13) C13B 0.167(3) 0.0694(17) 0.0675(17) -0.0068(13) 0.0162(19) -0.054(2) C14B 0.161(3) 0.0477(13) 0.0821(19) 0.0014(11) 0.002(2) -0.0174(16) C15B 0.113(2) 0.0520(12) 0.0756(16) 0.0039(11) 0.0036(14) -0.0096(12) N21B 0.0648(10) 0.0424(8) 0.0598(10) 0.0060(7) 0.0075(8) 0.0003(7) C21B 0.0491(10) 0.0400(9) 0.0514(10) 0.0026(7) 0.0007(8) -0.0008(7) C22B 0.0532(11) 0.0415(9) 0.0618(12) 0.0037(8) 0.0060(9) 0.0032(8) C23B 0.0718(14) 0.0422(10) 0.0634(13) 0.0059(8) -0.0003(11) 0.0051(9) C24B 0.0597(12) 0.0490(10) 0.0744(14) -0.0036(9) 0.0026(11) 0.0131(9) C25B 0.0547(11) 0.0485(10) 0.0633(12) -0.0001(9) 0.0098(9) 0.0013(8) C31B 0.0425(10) 0.0435(9) 0.0630(12) 0.0031(8) -0.0015(9) -0.0007(7) C32B 0.0534(11) 0.0447(9) 0.0495(11) -0.0036(7) 0.0058(9) -0.0076(8) C33B 0.0562(12) 0.0602(12) 0.0800(15) -0.0051(10) -0.0103(11) -0.0158(9) C34B 0.0695(14) 0.0678(13) 0.0719(15) 0.0007(11) -0.0231(12) -0.0057(11) C35B 0.0491(11) 0.0540(11) 0.0695(13) 0.0010(9) -0.0081(10) 0.0009(8) C36B 0.0419(9) 0.0438(9) 0.0477(10) -0.0001(7) 0.0003(8) -0.0002(7) C37B 0.0654(13) 0.0464(10) 0.0605(12) 0.0008(9) 0.0011(10) -0.0092(9) C38B 0.0431(10) 0.0441(9) 0.0608(12) 0.0058(8) 0.0006(8) 0.0013(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O11 C17 1.197(2) . ? O12 C17 1.313(2) . ? O13 C18 1.206(2) . ? O14 C18 1.322(2) . ? O15 C19 1.207(2) . ? O16 C19 1.324(2) . ? C11 C12 1.381(2) . ? C11 C16 1.389(2) . ? C11 C17 1.496(2) . ? C12 C13 1.391(2) . ? C13 C14 1.387(2) . ? C13 C18 1.488(2) . ? C14 C15 1.391(2) . ? C15 C16 1.385(2) . ? C15 C19 1.496(2) . ? N11A C13A 1.330(2) . ? N11A C12A 1.335(2) . ? C11A C15A 1.386(2) . ? C11A C12A 1.392(2) . ? C11A C37A 1.470(2) . ? C13A C14A 1.376(3) . ? C14A C15A 1.369(2) . ? N21A C22A 1.327(2) . ? N21A C23A 1.333(2) . ? C21A C25A 1.395(2) . ? C21A C22A 1.395(2) . ? C21A C38A 1.460(2) . ? C23A C24A 1.365(3) . ? C24A C25A 1.373(3) . ? O31A C31A 1.222(2) . ? C31A C36A 1.501(3) . ? C31A C32A 1.503(2) . ? C32A C37A 1.336(2) . ? C32A C33A 1.494(3) . ? C33A C34A 1.514(3) . ? C34A C35A 1.516(3) . ? C35A C36A 1.503(2) . ? C36A C38A 1.340(2) . ? O31B C31B 1.218(2) . ? N11B C13B 1.325(4) . ? N11B C12B 1.336(3) . ? C11B C15B 1.383(3) . ? C11B C12B 1.399(3) . ? C11B C37B 1.459(3) . ? C13B C14B 1.358(4) . ? C14B C15B 1.391(3) . ? N21B C22B 1.335(2) . ? N21B C23B 1.338(3) . ? C21B C22B 1.387(2) . ? C21B C25B 1.390(3) . ? C21B C38B 1.466(2) . ? C23B C24B 1.366(3) . ? C24B C25B 1.378(3) . ? C31B C32B 1.497(2) . ? C31B C36B 1.499(2) . ? C32B C37B 1.338(2) . ? C32B C33B 1.490(3) . ? C33B C34B 1.506(3) . ? C34B C35B 1.502(3) . ? C35B C36B 1.503(3) . ? C36B C38B 1.335(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 C11 C16 119.55(15) . . ? C12 C11 C17 120.54(16) . . ? C16 C11 C17 119.90(16) . . ? C11 C12 C13 120.75(16) . . ? C14 C13 C12 119.36(16) . . ? C14 C13 C18 122.94(15) . . ? C12 C13 C18 117.70(15) . . ? C13 C14 C15 120.28(15) . . ? C16 C15 C14 119.74(16) . . ? C16 C15 C19 122.13(16) . . ? C14 C15 C19 118.02(15) . . ? C15 C16 C11 120.32(16) . . ? O11 C17 O12 123.31(17) . . ? O11 C17 C11 123.45(18) . . ? O12 C17 C11 113.24(16) . . ? O13 C18 O14 124.01(17) . . ? O13 C18 C13 122.31(15) . . ? O14 C18 C13 113.68(16) . . ? O15 C19 O16 123.23(17) . . ? O15 C19 C15 123.37(17) . . ? O16 C19 C15 113.36(15) . . ? C13A N11A C12A 118.05(15) . . ? C15A C11A C12A 116.63(16) . . ? C15A C11A C37A 120.28(16) . . ? C12A C11A C37A 123.08(16) . . ? N11A C12A C11A 123.48(17) . . ? N11A C13A C14A 122.79(17) . . ? C15A C14A C13A 118.60(17) . . ? C14A C15A C11A 120.37(17) . . ? C22A N21A C23A 117.43(15) . . ? C25A C21A C22A 115.67(15) . . ? C25A C21A C38A 127.74(15) . . ? C22A C21A C38A 116.59(16) . . ? N21A C22A C21A 124.91(17) . . ? N21A C23A C24A 122.56(17) . . ? C23A C24A C25A 119.77(18) . . ? C24A C25A C21A 119.55(16) . . ? O31A C31A C36A 120.36(16) . . ? O31A C31A C32A 121.10(17) . . ? C36A C31A C32A 118.54(15) . . ? C37A C32A C33A 126.26(15) . . ? C37A C32A C31A 116.37(16) . . ? C33A C32A C31A 117.31(15) . . ? C32A C33A C34A 111.04(15) . . ? C33A C34A C35A 110.16(16) . . ? C36A C35A C34A 113.53(16) . . ? C38A C36A C31A 115.51(16) . . ? C38A C36A C35A 125.68(16) . . ? C31A C36A C35A 118.81(15) . . ? C32A C37A C11A 128.15(17) . . ? C36A C38A C21A 130.45(16) . . ? C13B N11B C12B 116.3(3) . . ? C15B C11B C12B 116.6(2) . . ? C15B C11B C37B 118.9(2) . . ? C12B C11B C37B 124.4(2) . . ? N11B C12B C11B 124.7(3) . . ? N11B C13B C14B 124.6(2) . . ? C13B C14B C15B 118.7(3) . . ? C11B C15B C14B 119.2(3) . . ? C22B N21B C23B 117.63(17) . . ? C22B C21B C25B 116.90(16) . . ? C22B C21B C38B 118.84(16) . . ? C25B C21B C38B 124.26(17) . . ? N21B C22B C21B 123.80(17) . . ? N21B C23B C24B 122.97(17) . . ? C23B C24B C25B 118.92(19) . . ? C24B C25B C21B 119.69(18) . . ? O31B C31B C32B 121.00(16) . . ? O31B C31B C36B 120.25(15) . . ? C32B C31B C36B 118.75(16) . . ? C37B C32B C33B 124.74(17) . . ? C37B C32B C31B 116.22(18) . . ? C33B C32B C31B 119.03(16) . . ? C32B C33B C34B 113.88(17) . . ? C35B C34B C33B 111.25(19) . . ? C34B C35B C36B 111.06(16) . . ? C38B C36B C31B 117.35(16) . . ? C38B C36B C35B 124.35(16) . . ? C31B C36B C35B 118.24(15) . . ? C32B C37B C11B 131.0(2) . . ? C36B C38B C21B 127.07(17) . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.225 _refine_diff_density_min -0.205 _refine_diff_density_rms 0.035