# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email kbiradha@yahoo.com _publ_contact_author_name 'Kumar Biradha' loop_ _publ_author_name K.Biradha R.Santra data_5 _database_code_depnum_ccdc_archive 'CCDC 688735' #TrackingRef '- kb1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2(1,5-bis(4-pyridyl)-1,4-pentadiene-3-one).(phloroglucinol).4(H2O) ; _chemical_name_common ;2(1,5-bis(4-pyridyl)-1,4-pentadiene-3- one).(phloroglucinol).4(H2O) ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H38 N4 O9' _chemical_formula_weight 670.70 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 12.873(2) _cell_length_b 15.947(3) _cell_length_c 16.881(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.206(5) _cell_angle_gamma 90.00 _cell_volume 3465.4(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4258 _cell_measurement_theta_min 1.58 _cell_measurement_theta_max 26 _exptl_crystal_description rhombic _exptl_crystal_colour brown _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.286 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1384 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.986 _exptl_absorpt_correction_T_max 0.989 _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 ? _diffrn_measurement_method 'Bruker Apex 2' _diffrn_detector_area_resol_mean hemisphere _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 43156 _diffrn_reflns_av_R_equivalents 0.0511 _diffrn_reflns_av_sigmaI/netI 0.0337 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 26.00 _reflns_number_total 6811 _reflns_number_gt 4258 _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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6811 _refine_ls_number_parameters 442 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1038 _refine_ls_R_factor_gt 0.0637 _refine_ls_wR_factor_ref 0.1999 _refine_ls_wR_factor_gt 0.1806 _refine_ls_goodness_of_fit_ref 1.221 _refine_ls_restrained_S_all 1.221 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.001 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 O11A O 0.02403(14) 0.40386(11) 0.14442(12) 0.0706(6) Uani 1 1 d . . . N21A N 0.41228(18) 0.12760(15) 0.33806(15) 0.0691(7) Uani 1 1 d . . . N31A N -0.33997(15) 0.16533(15) -0.07068(13) 0.0605(6) Uani 1 1 d . . . C11A C 0.04067(17) 0.32856(16) 0.14369(14) 0.0483(6) Uani 1 1 d . . . C12A C 0.13261(18) 0.29671(16) 0.18711(15) 0.0527(6) Uani 1 1 d . . . H12A H 0.1782 0.3368 0.2071 0.063 Uiso 1 1 calc R . . C13A C -0.02988(17) 0.27020(15) 0.10196(13) 0.0484(6) Uani 1 1 d . . . H13A H -0.0142 0.2133 0.1005 0.058 Uiso 1 1 calc R . . C21A C 0.3463(2) 0.07740(18) 0.3019(2) 0.0762(9) Uani 1 1 d . . . H21A H 0.3563 0.0199 0.3069 0.091 Uiso 1 1 calc R . . C22A C 0.2639(2) 0.10458(17) 0.25736(18) 0.0685(8) Uani 1 1 d . . . H22A H 0.2197 0.0658 0.2335 0.082 Uiso 1 1 calc R . . C23A C 0.24621(17) 0.18885(15) 0.24778(14) 0.0465(6) Uani 1 1 d . . . C24A C 0.31528(19) 0.24187(16) 0.28492(16) 0.0584(7) Uani 1 1 d . . . H24A H 0.3073 0.2997 0.2807 0.070 Uiso 1 1 calc R . . C25A C 0.3956(2) 0.20907(18) 0.32810(18) 0.0696(8) Uani 1 1 d . . . H25A H 0.4416 0.2463 0.3521 0.084 Uiso 1 1 calc R . . C26A C 0.15668(17) 0.21840(15) 0.20037(14) 0.0482(6) Uani 1 1 d . . . H26A H 0.1138 0.1778 0.1781 0.058 Uiso 1 1 calc R . . C31A C -0.34243(19) 0.24759(19) -0.06129(17) 0.0639(8) Uani 1 1 d . . . H31A H -0.3954 0.2773 -0.0863 0.077 Uiso 1 1 calc R . . C32A C -0.27147(19) 0.29207(17) -0.01676(16) 0.0589(7) Uani 1 1 d . . . H32A H -0.2773 0.3500 -0.0123 0.071 Uiso 1 1 calc R . . C33A C -0.19140(17) 0.25018(15) 0.02126(13) 0.0462(6) Uani 1 1 d . . . C34A C -0.1888(2) 0.16380(17) 0.01177(16) 0.0612(7) Uani 1 1 d . . . H34A H -0.1370 0.1323 0.0361 0.073 Uiso 1 1 calc R . . C35A C -0.2632(2) 0.12527(18) -0.03371(17) 0.0660(8) Uani 1 1 d . . . H35A H -0.2597 0.0673 -0.0391 0.079 Uiso 1 1 calc R . . C36A C -0.11454(18) 0.29766(15) 0.06684(14) 0.0484(6) Uani 1 1 d . . . H36A H -0.1273 0.3548 0.0716 0.058 Uiso 1 1 calc R . . O11B O 0.81838(15) 0.40924(13) 0.25176(13) 0.0793(6) Uani 1 1 d . . . N21B N 0.39830(16) 0.19208(15) 0.08188(13) 0.0602(6) Uani 1 1 d . . . N31B N 1.16126(17) 0.11953(16) 0.47536(14) 0.0656(6) Uani 1 1 d . . . C11B C 0.81812(18) 0.33404(18) 0.26422(15) 0.0546(6) Uani 1 1 d . . . C12B C 0.73535(19) 0.27950(17) 0.23104(15) 0.0546(6) Uani 1 1 d . . . H12B H 0.7392 0.2218 0.2384 0.065 Uiso 1 1 calc R . . C13B C 0.9028(2) 0.29889(18) 0.31226(16) 0.0611(7) Uani 1 1 d . . . H13B H 0.9503 0.3371 0.3330 0.073 Uiso 1 1 calc R . . C21B C 0.4717(2) 0.14813(17) 0.11858(17) 0.0661(8) Uani 1 1 d . . . H21B H 0.4651 0.0901 0.1197 0.079 Uiso 1 1 calc R . . C22B C 0.5566(2) 0.18309(17) 0.15485(16) 0.0612(7) Uani 1 1 d . . . H22B H 0.6060 0.1491 0.1792 0.073 Uiso 1 1 calc R . . C23B C 0.56857(18) 0.26910(15) 0.15501(14) 0.0490(6) Uani 1 1 d . . . C24B C 0.4920(2) 0.31481(17) 0.11758(16) 0.0594(7) Uani 1 1 d . . . H24B H 0.4961 0.3730 0.1164 0.071 Uiso 1 1 calc R . . C25B C 0.4101(2) 0.27515(18) 0.08218(17) 0.0644(7) Uani 1 1 d . . . H25B H 0.3601 0.3077 0.0570 0.077 Uiso 1 1 calc R . . C26B C 0.65691(19) 0.31144(16) 0.19159(15) 0.0534(6) Uani 1 1 d . . . H26B H 0.6577 0.3695 0.1861 0.064 Uiso 1 1 calc R . . C31B C 1.0867(2) 0.07287(18) 0.44334(17) 0.0687(8) Uani 1 1 d . . . H31B H 1.0872 0.0156 0.4539 0.082 Uiso 1 1 calc R . . C32B C 1.0093(2) 0.10357(18) 0.39579(16) 0.0620(7) Uani 1 1 d . . . H32B H 0.9595 0.0674 0.3749 0.074 Uiso 1 1 calc R . . C33B C 1.00511(18) 0.18721(17) 0.37896(14) 0.0505(6) Uani 1 1 d . . . C34B C 1.0821(2) 0.23697(17) 0.41111(17) 0.0632(7) Uani 1 1 d . . . H34B H 1.0835 0.2943 0.4010 0.076 Uiso 1 1 calc R . . C35B C 1.1570(2) 0.2005(2) 0.45835(17) 0.0692(8) Uani 1 1 d . . . H35B H 1.2080 0.2351 0.4798 0.083 Uiso 1 1 calc R . . C36B C 0.91899(19) 0.22016(17) 0.32907(15) 0.0557(7) Uani 1 1 d . . . H36B H 0.8726 0.1813 0.3080 0.067 Uiso 1 1 calc R . . O1 O 0.20153(12) 0.52060(11) 0.24962(10) 0.0606(5) Uani 1 1 d . . . H1O H 0.2113 0.5080 0.2004 0.091 Uiso 1 1 d R . . O2 O 0.53888(12) 0.42659(12) 0.31902(11) 0.0658(5) Uani 1 1 d . . . H2O H 0.5733 0.3982 0.3495 0.099 Uiso 1 1 d R . . O3 O 0.25722(13) 0.40173(11) 0.50242(10) 0.0611(5) Uani 1 1 d . . . H3O H 0.3016 0.3700 0.5255 0.092 Uiso 1 1 d R . . C1 C 0.26847(17) 0.48421(14) 0.30336(14) 0.0454(6) Uani 1 1 d . . . C2 C 0.37172(17) 0.47289(14) 0.28361(15) 0.0481(6) Uani 1 1 d . . . H2 H 0.3965 0.4888 0.2342 0.058 Uiso 1 1 calc R . . C3 C 0.43733(17) 0.43706(14) 0.33970(14) 0.0455(6) Uani 1 1 d . . . C4 C 0.40201(16) 0.41409(14) 0.41294(14) 0.0447(6) Uani 1 1 d . . . H4 H 0.4473 0.3915 0.4503 0.054 Uiso 1 1 calc R . . C5 C 0.29758(17) 0.42491(14) 0.43068(13) 0.0454(6) Uani 1 1 d . . . C6 C 0.23008(17) 0.46031(14) 0.37614(14) 0.0472(6) Uani 1 1 d . . . H6 H 0.1603 0.4678 0.3883 0.057 Uiso 1 1 calc R . . O1W O 0.25586(16) 0.49078(15) 0.09168(13) 0.0920(7) Uani 1 1 d . . . O2W O 0.00620(15) 0.01803(13) 0.20573(12) 0.0796(6) Uani 1 1 d . . . O3W O 0.05239(14) 0.05332(14) 0.05164(12) 0.0800(6) Uani 1 1 d . . . O4W O 0.54705(17) 0.03836(17) 0.43906(15) 0.1029(8) 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 O11A 0.0719(13) 0.0477(11) 0.0920(14) -0.0030(10) -0.0323(11) 0.0059(9) N21A 0.0589(14) 0.0632(16) 0.0851(17) 0.0078(12) -0.0179(12) 0.0112(12) N31A 0.0426(12) 0.0735(16) 0.0653(14) -0.0019(12) -0.0101(10) -0.0094(11) C11A 0.0424(13) 0.0497(15) 0.0527(14) 0.0015(11) -0.0093(11) 0.0017(11) C12A 0.0451(14) 0.0515(16) 0.0614(16) -0.0013(12) -0.0151(12) -0.0054(11) C13A 0.0443(14) 0.0488(14) 0.0519(14) -0.0012(11) -0.0072(11) 0.0014(11) C21A 0.073(2) 0.0474(17) 0.108(2) 0.0118(16) -0.0204(18) 0.0061(14) C22A 0.0627(18) 0.0442(16) 0.098(2) 0.0017(14) -0.0225(16) -0.0038(13) C23A 0.0381(13) 0.0470(14) 0.0545(14) -0.0005(11) -0.0027(10) -0.0002(10) C24A 0.0507(15) 0.0421(14) 0.0820(18) -0.0039(12) -0.0237(14) 0.0035(11) C25A 0.0574(17) 0.0601(18) 0.091(2) -0.0061(15) -0.0295(15) 0.0046(14) C26A 0.0392(13) 0.0474(15) 0.0581(14) -0.0051(11) -0.0091(11) -0.0006(11) C31A 0.0397(14) 0.076(2) 0.0757(18) -0.0067(15) -0.0193(13) 0.0094(13) C32A 0.0463(15) 0.0595(17) 0.0707(18) -0.0051(13) -0.0148(13) 0.0095(12) C33A 0.0369(13) 0.0560(16) 0.0457(13) 0.0011(11) -0.0021(10) 0.0004(11) C34A 0.0542(16) 0.0575(17) 0.0717(18) 0.0085(13) -0.0240(13) -0.0019(13) C35A 0.0660(18) 0.0550(17) 0.0769(19) 0.0038(14) -0.0150(15) -0.0105(13) C36A 0.0443(14) 0.0507(14) 0.0500(14) 0.0017(11) -0.0075(11) 0.0007(11) O11B 0.0702(13) 0.0592(13) 0.1082(17) 0.0014(11) -0.0285(11) 0.0006(10) N21B 0.0500(13) 0.0662(15) 0.0644(14) -0.0095(11) -0.0016(11) -0.0041(11) N31B 0.0557(14) 0.0720(17) 0.0690(15) 0.0085(12) -0.0128(11) 0.0054(12) C11B 0.0441(14) 0.0635(18) 0.0562(15) -0.0008(13) -0.0052(11) 0.0064(12) C12B 0.0518(15) 0.0533(15) 0.0585(15) 0.0044(12) -0.0034(12) 0.0047(12) C13B 0.0542(16) 0.0633(19) 0.0656(17) 0.0017(13) -0.0094(13) -0.0040(13) C21B 0.0691(19) 0.0500(17) 0.0791(19) -0.0011(14) -0.0066(15) -0.0003(14) C22B 0.0572(16) 0.0557(17) 0.0706(17) 0.0032(13) -0.0122(13) 0.0068(13) C23B 0.0456(14) 0.0500(15) 0.0513(14) -0.0005(11) -0.0013(11) 0.0024(11) C24B 0.0549(16) 0.0495(15) 0.0737(18) -0.0009(13) -0.0137(14) 0.0029(12) C25B 0.0512(16) 0.0656(19) 0.0761(19) -0.0021(14) -0.0163(14) 0.0085(13) C26B 0.0507(15) 0.0481(15) 0.0613(16) -0.0023(12) -0.0061(12) 0.0039(11) C31B 0.0709(19) 0.0550(17) 0.080(2) 0.0042(14) -0.0172(16) 0.0058(14) C32B 0.0583(17) 0.0612(18) 0.0665(17) -0.0028(13) -0.0131(14) -0.0004(13) C33B 0.0420(13) 0.0611(17) 0.0482(14) 0.0010(11) -0.0021(11) -0.0002(11) C34B 0.0593(17) 0.0572(17) 0.0729(18) 0.0119(13) -0.0083(14) -0.0010(13) C35B 0.0532(17) 0.076(2) 0.078(2) 0.0048(16) -0.0161(15) -0.0131(14) C36B 0.0510(15) 0.0596(17) 0.0563(15) -0.0020(12) -0.0005(12) -0.0025(12) O1 0.0506(10) 0.0743(12) 0.0568(11) 0.0079(9) -0.0095(8) 0.0142(9) O2 0.0371(9) 0.0844(13) 0.0761(12) 0.0182(10) 0.0032(8) 0.0140(9) O3 0.0456(10) 0.0796(13) 0.0582(11) 0.0107(9) 0.0050(8) 0.0187(8) C1 0.0416(13) 0.0384(13) 0.0561(14) -0.0012(11) -0.0115(11) 0.0049(10) C2 0.0424(14) 0.0472(14) 0.0547(14) 0.0038(11) -0.0039(11) 0.0005(11) C3 0.0338(12) 0.0426(13) 0.0599(15) -0.0009(11) -0.0030(11) 0.0023(10) C4 0.0355(12) 0.0463(13) 0.0523(14) 0.0000(11) -0.0078(10) 0.0057(10) C5 0.0422(13) 0.0434(13) 0.0506(14) -0.0035(10) -0.0022(11) 0.0030(10) C6 0.0315(12) 0.0482(14) 0.0618(15) -0.0040(11) -0.0046(11) 0.0055(10) O1W 0.0677(13) 0.1208(19) 0.0875(15) -0.0073(13) -0.0074(11) -0.0308(12) O2W 0.0653(12) 0.0974(16) 0.0759(13) 0.0141(11) -0.0142(10) -0.0124(11) O3W 0.0563(11) 0.1062(17) 0.0774(13) -0.0061(11) 0.0045(10) -0.0083(11) O4W 0.0696(14) 0.1270(19) 0.1120(19) 0.0402(15) -0.0016(13) 0.0304(13) _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 O11A C11A 1.220(3) . ? N21A C21A 1.316(4) . ? N21A C25A 1.327(3) . ? N31A C31A 1.322(3) . ? N31A C35A 1.331(3) . ? C11A C13A 1.477(3) . ? C11A C12A 1.480(3) . ? C12A C26A 1.306(3) . ? C12A H12A 0.9300 . ? C13A C36A 1.314(3) . ? C13A H13A 0.9300 . ? C21A C22A 1.368(4) . ? C21A H21A 0.9300 . ? C22A C23A 1.372(3) . ? C22A H22A 0.9300 . ? C23A C24A 1.376(3) . ? C23A C26A 1.478(3) . ? C24A C25A 1.367(3) . ? C24A H24A 0.9300 . ? C25A H25A 0.9300 . ? C26A H26A 0.9300 . ? C31A C32A 1.378(3) . ? C31A H31A 0.9300 . ? C32A C33A 1.384(3) . ? C32A H32A 0.9300 . ? C33A C34A 1.387(3) . ? C33A C36A 1.462(3) . ? C34A C35A 1.370(3) . ? C34A H34A 0.9300 . ? C35A H35A 0.9300 . ? C36A H36A 0.9300 . ? O11B C11B 1.218(3) . ? N21B C21B 1.328(3) . ? N21B C25B 1.334(3) . ? N31B C35B 1.323(3) . ? N31B C31B 1.327(3) . ? C11B C13B 1.468(4) . ? C11B C12B 1.484(4) . ? C12B C26B 1.311(3) . ? C12B H12B 0.9300 . ? C13B C36B 1.304(3) . ? C13B H13B 0.9300 . ? C21B C22B 1.370(4) . ? C21B H21B 0.9300 . ? C22B C23B 1.380(3) . ? C22B H22B 0.9300 . ? C23B C24B 1.378(3) . ? C23B C26B 1.458(3) . ? C24B C25B 1.365(4) . ? C24B H24B 0.9300 . ? C25B H25B 0.9300 . ? C26B H26B 0.9300 . ? C31B C32B 1.368(4) . ? C31B H31B 0.9300 . ? C32B C33B 1.365(4) . ? C32B H32B 0.9300 . ? C33B C34B 1.380(4) . ? C33B C36B 1.486(3) . ? C34B C35B 1.378(4) . ? C34B H34B 0.9300 . ? C35B H35B 0.9300 . ? C36B H36B 0.9300 . ? O1 C1 1.377(3) . ? O1 H1O 0.8637 . ? O2 C3 1.364(3) . ? O2 H2O 0.8153 . ? O3 C5 1.370(3) . ? O3 H3O 0.8559 . ? C1 C6 1.380(3) . ? C1 C2 1.383(3) . ? C2 C3 1.389(3) . ? C2 H2 0.9300 . ? C3 C4 1.369(3) . ? C4 C5 1.389(3) . ? C4 H4 0.9300 . ? C5 C6 1.384(3) . ? C6 H6 0.9300 . ? 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 C21A N21A C25A 115.6(2) . . ? C31A N31A C35A 116.0(2) . . ? O11A C11A C13A 121.2(2) . . ? O11A C11A C12A 118.2(2) . . ? C13A C11A C12A 120.6(2) . . ? C26A C12A C11A 127.0(2) . . ? C26A C12A H12A 116.5 . . ? C11A C12A H12A 116.5 . . ? C36A C13A C11A 120.8(2) . . ? C36A C13A H13A 119.6 . . ? C11A C13A H13A 119.6 . . ? N21A C21A C22A 124.1(3) . . ? N21A C21A H21A 118.0 . . ? C22A C21A H21A 118.0 . . ? C21A C22A C23A 120.2(3) . . ? C21A C22A H22A 119.9 . . ? C23A C22A H22A 119.9 . . ? C22A C23A C24A 116.2(2) . . ? C22A C23A C26A 120.3(2) . . ? C24A C23A C26A 123.5(2) . . ? C25A C24A C23A 119.6(2) . . ? C25A C24A H24A 120.2 . . ? C23A C24A H24A 120.2 . . ? N21A C25A C24A 124.3(3) . . ? N21A C25A H25A 117.8 . . ? C24A C25A H25A 117.8 . . ? C12A C26A C23A 125.6(2) . . ? C12A C26A H26A 117.2 . . ? C23A C26A H26A 117.2 . . ? N31A C31A C32A 124.1(2) . . ? N31A C31A H31A 118.0 . . ? C32A C31A H31A 118.0 . . ? C31A C32A C33A 119.7(2) . . ? C31A C32A H32A 120.1 . . ? C33A C32A H32A 120.1 . . ? C32A C33A C34A 116.4(2) . . ? C32A C33A C36A 119.7(2) . . ? C34A C33A C36A 123.9(2) . . ? C35A C34A C33A 119.5(2) . . ? C35A C34A H34A 120.2 . . ? C33A C34A H34A 120.2 . . ? N31A C35A C34A 124.3(3) . . ? N31A C35A H35A 117.8 . . ? C34A C35A H35A 117.8 . . ? C13A C36A C33A 128.6(2) . . ? C13A C36A H36A 115.7 . . ? C33A C36A H36A 115.7 . . ? C21B N21B C25B 116.2(2) . . ? C35B N31B C31B 115.4(2) . . ? O11B C11B C13B 118.0(2) . . ? O11B C11B C12B 121.0(2) . . ? C13B C11B C12B 121.1(2) . . ? C26B C12B C11B 121.0(2) . . ? C26B C12B H12B 119.5 . . ? C11B C12B H12B 119.5 . . ? C36B C13B C11B 127.3(3) . . ? C36B C13B H13B 116.4 . . ? C11B C13B H13B 116.4 . . ? N21B C21B C22B 124.0(3) . . ? N21B C21B H21B 118.0 . . ? C22B C21B H21B 118.0 . . ? C21B C22B C23B 119.6(2) . . ? C21B C22B H22B 120.2 . . ? C23B C22B H22B 120.2 . . ? C24B C23B C22B 116.5(2) . . ? C24B C23B C26B 120.3(2) . . ? C22B C23B C26B 123.2(2) . . ? C25B C24B C23B 120.4(3) . . ? C25B C24B H24B 119.8 . . ? C23B C24B H24B 119.8 . . ? N21B C25B C24B 123.4(2) . . ? N21B C25B H25B 118.3 . . ? C24B C25B H25B 118.3 . . ? C12B C26B C23B 129.3(2) . . ? C12B C26B H26B 115.3 . . ? C23B C26B H26B 115.3 . . ? N31B C31B C32B 124.2(3) . . ? N31B C31B H31B 117.9 . . ? C32B C31B H31B 117.9 . . ? C33B C32B C31B 120.0(3) . . ? C33B C32B H32B 120.0 . . ? C31B C32B H32B 120.0 . . ? C32B C33B C34B 116.9(2) . . ? C32B C33B C36B 119.5(2) . . ? C34B C33B C36B 123.6(2) . . ? C35B C34B C33B 119.0(3) . . ? C35B C34B H34B 120.5 . . ? C33B C34B H34B 120.5 . . ? N31B C35B C34B 124.5(3) . . ? N31B C35B H35B 117.8 . . ? C34B C35B H35B 117.8 . . ? C13B C36B C33B 125.6(3) . . ? C13B C36B H36B 117.2 . . ? C33B C36B H36B 117.2 . . ? C1 O1 H1O 116.3 . . ? C3 O2 H2O 115.2 . . ? C5 O3 H3O 107.9 . . ? O1 C1 C6 118.5(2) . . ? O1 C1 C2 119.7(2) . . ? C6 C1 C2 121.7(2) . . ? C1 C2 C3 118.2(2) . . ? C1 C2 H2 120.9 . . ? C3 C2 H2 120.9 . . ? O2 C3 C4 121.3(2) . . ? O2 C3 C2 117.2(2) . . ? C4 C3 C2 121.5(2) . . ? C3 C4 C5 119.1(2) . . ? C3 C4 H4 120.4 . . ? C5 C4 H4 120.4 . . ? O3 C5 C6 117.3(2) . . ? O3 C5 C4 121.8(2) . . ? C6 C5 C4 120.9(2) . . ? C1 C6 C5 118.6(2) . . ? C1 C6 H6 120.7 . . ? C5 C6 H6 120.7 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.436 _refine_diff_density_min -0.198 _refine_diff_density_rms 0.052 data_4 _database_code_depnum_ccdc_archive 'CCDC 793077' #TrackingRef '- kb1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4(1,5-bis(4-pyridyl)-1,4-pentadiene-3-one).3(phloroglucinol).4(H2O) ; _chemical_name_common ;4(1,5-bis(4-pyridyl)-1,4-pentadiene-3- one).3(phloroglucinol).4(H2O) ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C78 H74 N8 O17' _chemical_formula_weight 1395.45 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 19.3013(16) _cell_length_b 15.3054(13) _cell_length_c 28.1176(19) _cell_angle_alpha 90.00 _cell_angle_beta 122.935(4) _cell_angle_gamma 90.00 _cell_volume 6971.4(10) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 15027 _cell_measurement_theta_min 1.26 _cell_measurement_theta_max 27.00 _exptl_crystal_description block _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.330 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2936 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.984 _exptl_absorpt_correction_T_max 0.989 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 CCD APEX-2' _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 91277 _diffrn_reflns_av_R_equivalents 0.0866 _diffrn_reflns_av_sigmaI/netI 0.0690 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 1.26 _diffrn_reflns_theta_max 27.00 _reflns_number_total 15072 _reflns_number_gt 8246 _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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 15072 _refine_ls_number_parameters 908 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1256 _refine_ls_R_factor_gt 0.0592 _refine_ls_wR_factor_ref 0.1901 _refine_ls_wR_factor_gt 0.1616 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0.001 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 0.18465(10) 0.16024(11) 0.25390(7) 0.0367(4) Uani 1 1 d . . . N11A N 0.54194(12) 0.39678(14) 0.45452(9) 0.0329(5) Uani 1 1 d . . . N21A N -0.21290(12) 0.33463(15) 0.06106(9) 0.0349(5) Uani 1 1 d . . . C1A C 0.17694(14) 0.23967(16) 0.25550(10) 0.0273(6) Uani 1 1 d . . . C10A C 0.24765(14) 0.29535(16) 0.29605(10) 0.0307(6) Uani 1 1 d . . . H10A H 0.2386 0.3557 0.2986 0.037 Uiso 1 1 calc R . . C11A C 0.32352(13) 0.26292(16) 0.32900(10) 0.0274(6) Uani 1 1 d . . . H11A H 0.3304 0.2027 0.3244 0.033 Uiso 1 1 calc R . . C12A C 0.39720(14) 0.31050(15) 0.37143(10) 0.0255(5) Uani 1 1 d . . . C13A C 0.47343(14) 0.26946(17) 0.39876(11) 0.0324(6) Uani 1 1 d . . . H13A H 0.4778 0.2107 0.3897 0.039 Uiso 1 1 calc R . . C14A C 0.54321(15) 0.31434(17) 0.43926(11) 0.0340(6) Uani 1 1 d . . . H14A H 0.5948 0.2850 0.4572 0.041 Uiso 1 1 calc R . . C15A C 0.46818(15) 0.43615(17) 0.42883(11) 0.0375(7) Uani 1 1 d . . . H15A H 0.4656 0.4947 0.4391 0.045 Uiso 1 1 calc R . . C16A C 0.39575(15) 0.39597(16) 0.38826(11) 0.0358(6) Uani 1 1 d . . . H16A H 0.3448 0.4264 0.3717 0.043 Uiso 1 1 calc R . . C20A C 0.09688(14) 0.28320(17) 0.21728(10) 0.0300(6) Uani 1 1 d . . . H20A H 0.0924 0.3444 0.2205 0.036 Uiso 1 1 calc R . . C21A C 0.03101(13) 0.23863(16) 0.17844(10) 0.0275(6) Uani 1 1 d . . . H21A H 0.0381 0.1775 0.1770 0.033 Uiso 1 1 calc R . . C22A C -0.05175(14) 0.27370(16) 0.13730(10) 0.0269(5) Uani 1 1 d . . . C23A C -0.11676(14) 0.21647(17) 0.10478(10) 0.0314(6) Uani 1 1 d . . . H23A H -0.1074 0.1552 0.1078 0.038 Uiso 1 1 calc R . . C24A C -0.19538(15) 0.24929(18) 0.06788(11) 0.0350(6) Uani 1 1 d . . . H24A H -0.2391 0.2091 0.0463 0.042 Uiso 1 1 calc R . . C25A C -0.14960(15) 0.38902(17) 0.09112(11) 0.0348(6) Uani 1 1 d . . . H25A H -0.1605 0.4500 0.0860 0.042 Uiso 1 1 calc R . . C26A C -0.06961(14) 0.36281(16) 0.12908(11) 0.0313(6) Uani 1 1 d . . . H26A H -0.0271 0.4048 0.1494 0.038 Uiso 1 1 calc R . . O1B O 0.60749(10) 0.15695(12) 0.21123(7) 0.0391(5) Uani 1 1 d . . . N11B N 0.97714(13) 0.38960(14) 0.39815(9) 0.0385(6) Uani 1 1 d . . . N21B N 0.21551(12) 0.34929(14) 0.02985(9) 0.0340(5) Uani 1 1 d . . . C1B C 0.60410(14) 0.23707(17) 0.21271(10) 0.0304(6) Uani 1 1 d . . . C10B C 0.67765(14) 0.29024(17) 0.25125(10) 0.0333(6) Uani 1 1 d . . . H10B H 0.6722 0.3520 0.2501 0.040 Uiso 1 1 calc R . . C11B C 0.75116(14) 0.25532(16) 0.28742(10) 0.0293(6) Uani 1 1 d . . . H11B H 0.7542 0.1933 0.2888 0.035 Uiso 1 1 calc R . . C12B C 0.82795(14) 0.30275(15) 0.32535(10) 0.0264(5) Uani 1 1 d . . . C13B C 0.83295(15) 0.39318(17) 0.32800(11) 0.0360(6) Uani 1 1 d . . . H13B H 0.7849 0.4273 0.3046 0.043 Uiso 1 1 calc R . . C14B C 0.90701(15) 0.43335(17) 0.36424(12) 0.0394(7) Uani 1 1 d . . . H14B H 0.9086 0.4954 0.3653 0.047 Uiso 1 1 calc R . . C15B C 0.97290(15) 0.30250(17) 0.39604(11) 0.0352(6) Uani 1 1 d . . . H15B H 1.0220 0.2702 0.4201 0.042 Uiso 1 1 calc R . . C16B C 0.90064(14) 0.25689(16) 0.36052(10) 0.0308(6) Uani 1 1 d . . . H16B H 0.9007 0.1948 0.3602 0.037 Uiso 1 1 calc R . . C20B C 0.52597(14) 0.28419(17) 0.17517(10) 0.0320(6) Uani 1 1 d . . . H20B H 0.5254 0.3462 0.1767 0.038 Uiso 1 1 calc R . . C21B C 0.45670(14) 0.24214(17) 0.13942(10) 0.0299(6) Uani 1 1 d . . . H21B H 0.4602 0.1803 0.1386 0.036 Uiso 1 1 calc R . . C22B C 0.37471(13) 0.28101(16) 0.10079(10) 0.0260(5) Uani 1 1 d . . . C23B C 0.30673(14) 0.22706(16) 0.07047(10) 0.0299(6) Uani 1 1 d . . . H23B H 0.3133 0.1654 0.0730 0.036 Uiso 1 1 calc R . . C24B C 0.22901(14) 0.26351(17) 0.03635(11) 0.0333(6) Uani 1 1 d . . . H24B H 0.1830 0.2254 0.0166 0.040 Uiso 1 1 calc R . . C25B C 0.28195(15) 0.40089(17) 0.05810(12) 0.0396(7) Uani 1 1 d . . . H25B H 0.2738 0.4623 0.0535 0.047 Uiso 1 1 calc R . . C26B C 0.36129(15) 0.37056(17) 0.09340(12) 0.0364(6) Uani 1 1 d . . . H26B H 0.4062 0.4102 0.1124 0.044 Uiso 1 1 calc R . . O1C O 0.57957(10) 0.14743(12) 0.08311(8) 0.0425(5) Uani 1 1 d . . . N11C N 0.18196(13) 0.30593(15) -0.12740(9) 0.0381(6) Uani 1 1 d . . . N21C N 0.93218(12) 0.41101(15) 0.25569(9) 0.0360(5) Uani 1 1 d . . . C1C C 0.57167(14) 0.22609(17) 0.07575(10) 0.0307(6) Uani 1 1 d . . . C10C C 0.49127(15) 0.26537(17) 0.03153(11) 0.0342(6) Uani 1 1 d . . . H10C H 0.4894 0.3257 0.0229 0.041 Uiso 1 1 calc R . . C11C C 0.42214(15) 0.21894(17) 0.00374(11) 0.0326(6) Uani 1 1 d . . . H11C H 0.4261 0.1590 0.0136 0.039 Uiso 1 1 calc R . . C12C C 0.34012(14) 0.25092(17) -0.04072(10) 0.0301(6) Uani 1 1 d . . . C13C C 0.32507(16) 0.33649(17) -0.06022(11) 0.0373(6) Uani 1 1 d . . . H13C H 0.3685 0.3782 -0.0443 0.045 Uiso 1 1 calc R . . C14C C 0.24585(17) 0.3601(2) -0.10319(12) 0.0437(7) Uani 1 1 d . . . H14C H 0.2367 0.4189 -0.1161 0.052 Uiso 1 1 calc R . . C15C C 0.19699(15) 0.2234(2) -0.10847(11) 0.0392(7) Uani 1 1 d . . . H15C H 0.1524 0.1831 -0.1251 0.047 Uiso 1 1 calc R . . C16C C 0.27374(15) 0.19393(17) -0.06621(11) 0.0346(6) Uani 1 1 d . . . H16C H 0.2811 0.1346 -0.0545 0.042 Uiso 1 1 calc R . . C20C C 0.63983(14) 0.28773(16) 0.10980(10) 0.0307(6) Uani 1 1 d . . . H20C H 0.6288 0.3487 0.1060 0.037 Uiso 1 1 calc R . . C21C C 0.71618(14) 0.25983(16) 0.14564(10) 0.0290(6) Uani 1 1 d . . . H21C H 0.7246 0.1985 0.1474 0.035 Uiso 1 1 calc R . . C22C C 0.78920(14) 0.31361(16) 0.18289(10) 0.0267(5) Uani 1 1 d . . . C23C C 0.78678(15) 0.40457(16) 0.18505(11) 0.0329(6) Uani 1 1 d . . . H23C H 0.7364 0.4351 0.1616 0.039 Uiso 1 1 calc R . . C24C C 0.85864(15) 0.44952(17) 0.22174(11) 0.0364(6) Uani 1 1 d . . . H24C H 0.8559 0.5114 0.2230 0.044 Uiso 1 1 calc R . . C25C C 0.93346(15) 0.32421(17) 0.25353(11) 0.0328(6) Uani 1 1 d . . . H25C H 0.9846 0.2953 0.2776 0.039 Uiso 1 1 calc R . . C26C C 0.86461(14) 0.27357(16) 0.21823(10) 0.0301(6) Uani 1 1 d . . . H26C H 0.8692 0.2118 0.2183 0.036 Uiso 1 1 calc R . . O1D O 0.15493(10) 0.15635(11) 0.13648(8) 0.0380(5) Uani 1 1 d . . . N11D N -0.23663(12) 0.30228(14) -0.09083(9) 0.0344(5) Uani 1 1 d . . . N21D N 0.51001(12) 0.42316(15) 0.28867(9) 0.0378(5) Uani 1 1 d . . . C1D C 0.14732(14) 0.23347(16) 0.12282(10) 0.0297(6) Uani 1 1 d . . . C10D C 0.06907(14) 0.26941(16) 0.07617(11) 0.0321(6) Uani 1 1 d . . . H10D H 0.0643 0.3309 0.0707 0.038 Uiso 1 1 calc R . . C11D C 0.00484(14) 0.21972(16) 0.04140(10) 0.0306(6) Uani 1 1 d . . . H11D H 0.0124 0.1583 0.0467 0.037 Uiso 1 1 calc R . . C12D C -0.07708(14) 0.25001(16) -0.00467(10) 0.0297(6) Uani 1 1 d . . . C13D C -0.09629(15) 0.33740(16) -0.01888(11) 0.0339(6) Uani 1 1 d . . . H13D H -0.0554 0.3812 0.0006 0.041 Uiso 1 1 calc R . . C14D C -0.17533(15) 0.35978(18) -0.06161(11) 0.0361(6) Uani 1 1 d . . . H14D H -0.1871 0.4199 -0.0710 0.043 Uiso 1 1 calc R . . C15D C -0.21773(15) 0.21858(18) -0.07703(11) 0.0377(7) Uani 1 1 d . . . H15D H -0.2600 0.1762 -0.0970 0.045 Uiso 1 1 calc R . . C16D C -0.13999(16) 0.19001(17) -0.03515(11) 0.0358(6) Uani 1 1 d . . . H16D H -0.1297 0.1294 -0.0273 0.043 Uiso 1 1 calc R . . C20D C 0.21695(14) 0.29490(16) 0.15362(10) 0.0303(6) Uani 1 1 d . . . H20D H 0.2063 0.3558 0.1470 0.036 Uiso 1 1 calc R . . C21D C 0.29340(14) 0.26877(17) 0.18995(11) 0.0319(6) Uani 1 1 d . . . H21D H 0.3018 0.2074 0.1950 0.038 Uiso 1 1 calc R . . C22D C 0.36676(14) 0.32369(16) 0.22344(10) 0.0285(6) Uani 1 1 d . . . C23D C 0.36481(15) 0.41469(17) 0.22062(11) 0.0343(6) Uani 1 1 d . . . H23D H 0.3143 0.4445 0.1962 0.041 Uiso 1 1 calc R . . C24D C 0.43670(15) 0.46066(18) 0.25354(12) 0.0388(7) Uani 1 1 d . . . H24D H 0.4343 0.5226 0.2513 0.047 Uiso 1 1 calc R . . C25D C 0.51192(16) 0.33647(19) 0.29187(11) 0.0398(7) Uani 1 1 d . . . H25D H 0.5634 0.3087 0.3169 0.048 Uiso 1 1 calc R . . C26D C 0.44252(15) 0.28493(18) 0.26054(11) 0.0365(6) Uani 1 1 d . . . H26D H 0.4467 0.2232 0.2644 0.044 Uiso 1 1 calc R . . O1E O 0.08917(11) 0.05668(14) 0.00197(8) 0.0511(6) Uani 1 1 d . . . H1 H 0.0542 0.0656 -0.0416 0.077 Uiso 1 1 d R . . O3E O 0.30912(10) -0.02983(12) -0.01855(7) 0.0408(5) Uani 1 1 d . . . H2 H 0.3676 -0.0592 0.0054 0.061 Uiso 1 1 d R . . O5E O 0.34792(11) 0.00555(14) 0.16521(8) 0.0510(5) Uani 1 1 d . . . H3 H 0.4053 -0.0280 0.1841 0.076 Uiso 1 1 d R . . C1E C 0.16860(15) 0.03407(16) 0.02314(11) 0.0336(6) Uani 1 1 d . . . C2E C 0.19896(14) 0.01438(16) -0.01048(11) 0.0336(6) Uani 1 1 d . . . H2E H 0.1643 0.0178 -0.0506 0.040 Uiso 1 1 calc R . . C3E C 0.28120(15) -0.01043(16) 0.01590(11) 0.0319(6) Uani 1 1 d . . . C4E C 0.33320(15) -0.01440(17) 0.07468(11) 0.0343(6) Uani 1 1 d . . . H4E H 0.3896 -0.0303 0.0924 0.041 Uiso 1 1 calc R . . C5E C 0.30021(15) 0.00556(16) 0.10697(11) 0.0347(6) Uani 1 1 d . . . C6E C 0.21877(15) 0.02931(16) 0.08179(11) 0.0339(6) Uani 1 1 d . . . H6E H 0.1971 0.0423 0.1043 0.041 Uiso 1 1 calc R . . O1F O -0.02930(10) 0.62441(11) 0.19648(7) 0.0334(4) Uani 1 1 d . . . H4 H -0.0800 0.6466 0.1740 0.050 Uiso 1 1 d R . . O3F O 0.18015(10) 0.48728(11) 0.18287(8) 0.0381(5) Uani 1 1 d . . . H5 H 0.2150 0.5042 0.2206 0.057 Uiso 1 1 d R . . O5F O -0.07130(10) 0.55918(11) 0.01532(7) 0.0338(4) Uani 1 1 d . . . H6 H -0.1181 0.5861 0.0025 0.051 Uiso 1 1 d R . . C1F C -0.00410(13) 0.59038(15) 0.16335(10) 0.0259(5) Uani 1 1 d . . . C2F C 0.07400(14) 0.55402(15) 0.19029(11) 0.0285(6) Uani 1 1 d . . . H2F H 0.1080 0.5522 0.2305 0.034 Uiso 1 1 calc R . . C3F C 0.10227(14) 0.52007(15) 0.15792(11) 0.0276(6) Uani 1 1 d . . . C4F C 0.05307(14) 0.52006(15) 0.09971(10) 0.0280(6) Uani 1 1 d . . . H4F H 0.0721 0.4948 0.0780 0.034 Uiso 1 1 calc R . . C5F C -0.02472(14) 0.55741(15) 0.07322(10) 0.0269(5) Uani 1 1 d . . . C6F C -0.05431(13) 0.59308(14) 0.10450(10) 0.0262(5) Uani 1 1 d . . . H6F H -0.1077 0.6187 0.0860 0.031 Uiso 1 1 calc R . . O1G O 0.63709(10) 0.07503(12) 0.51697(7) 0.0400(5) Uani 1 1 d . . . H7 H 0.6903 0.1131 0.5310 0.060 Uiso 1 1 d R . . O3G O 0.39103(10) -0.00400(12) 0.34560(7) 0.0402(5) Uani 1 1 d . . . H8 H 0.3538 0.0162 0.3022 0.060 Uiso 1 1 d R . . O5G O 0.60610(10) 0.13361(12) 0.33842(7) 0.0362(4) Uani 1 1 d . . . H9 H 0.6552 0.1554 0.3607 0.054 Uiso 1 1 d R . . C1G C 0.59305(14) 0.07157(16) 0.45909(11) 0.0292(6) Uani 1 1 d . . . C2G C 0.51513(15) 0.03407(16) 0.43103(11) 0.0315(6) Uani 1 1 d . . . H2G H 0.4938 0.0104 0.4518 0.038 Uiso 1 1 calc R . . C3G C 0.46886(14) 0.03169(15) 0.37228(11) 0.0302(6) Uani 1 1 d . . . C4G C 0.49991(14) 0.06422(15) 0.34131(11) 0.0288(6) Uani 1 1 d . . . H4G H 0.4682 0.0611 0.3011 0.035 Uiso 1 1 calc R . . C5G C 0.57793(14) 0.10128(15) 0.37016(10) 0.0277(6) Uani 1 1 d . . . C6G C 0.62503(14) 0.10570(15) 0.42901(10) 0.0286(6) Uani 1 1 d . . . H6G H 0.6783 0.1317 0.4484 0.034 Uiso 1 1 calc R . . O1W O 0.30119(11) 0.05552(11) 0.23890(8) 0.0404(5) Uiso 1 1 d . . . O2W O 0.22032(12) 0.52714(13) 0.35936(9) 0.0524(5) Uiso 1 1 d . . . O3W O 0.27544(11) 0.54378(12) 0.28817(8) 0.0458(5) Uiso 1 1 d . . . O4W O 0.05129(11) 0.54165(12) 0.30778(8) 0.0452(5) 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 0.0296(9) 0.0336(10) 0.0382(11) -0.0005(8) 0.0128(9) -0.0008(8) N11A 0.0238(11) 0.0390(13) 0.0317(13) -0.0012(10) 0.0124(10) -0.0073(9) N21A 0.0257(11) 0.0463(14) 0.0302(13) 0.0054(10) 0.0135(10) -0.0004(10) C1A 0.0238(12) 0.0344(15) 0.0229(14) 0.0009(11) 0.0122(11) -0.0016(10) C10A 0.0266(13) 0.0334(14) 0.0291(15) 0.0003(11) 0.0133(12) -0.0017(11) C11A 0.0256(13) 0.0289(13) 0.0274(14) -0.0016(11) 0.0140(12) -0.0013(10) C12A 0.0244(12) 0.0303(13) 0.0224(13) -0.0004(10) 0.0131(11) -0.0047(10) C13A 0.0253(13) 0.0362(15) 0.0338(15) -0.0022(12) 0.0148(12) -0.0010(11) C14A 0.0219(12) 0.0408(16) 0.0383(16) -0.0011(12) 0.0157(12) 0.0010(11) C15A 0.0337(14) 0.0303(14) 0.0406(17) -0.0030(12) 0.0151(13) -0.0046(11) C16A 0.0279(13) 0.0324(15) 0.0374(16) 0.0046(12) 0.0114(12) 0.0029(11) C20A 0.0254(13) 0.0329(14) 0.0298(15) -0.0005(11) 0.0138(12) 0.0002(11) C21A 0.0231(12) 0.0305(13) 0.0284(14) 0.0011(11) 0.0137(11) -0.0011(10) C22A 0.0232(12) 0.0328(14) 0.0246(14) 0.0015(11) 0.0129(11) -0.0008(10) C23A 0.0299(13) 0.0331(14) 0.0276(14) -0.0041(11) 0.0134(12) -0.0043(11) C24A 0.0256(13) 0.0419(16) 0.0289(15) -0.0023(12) 0.0092(12) -0.0061(11) C25A 0.0271(13) 0.0370(15) 0.0405(16) 0.0063(12) 0.0185(13) 0.0007(11) C26A 0.0246(12) 0.0325(14) 0.0331(15) 0.0026(11) 0.0132(12) -0.0031(10) O1B 0.0271(9) 0.0381(11) 0.0425(12) 0.0025(9) 0.0126(9) 0.0019(8) N11B 0.0294(12) 0.0388(13) 0.0415(14) -0.0052(11) 0.0156(11) -0.0039(10) N21B 0.0233(11) 0.0402(13) 0.0324(13) -0.0014(10) 0.0111(10) 0.0002(9) C1B 0.0243(13) 0.0374(15) 0.0282(15) 0.0022(11) 0.0133(12) 0.0007(11) C10B 0.0274(13) 0.0363(15) 0.0324(15) 0.0001(12) 0.0139(12) 0.0004(11) C11B 0.0281(13) 0.0328(14) 0.0267(14) 0.0006(11) 0.0148(12) -0.0013(11) C12B 0.0225(12) 0.0317(14) 0.0256(14) -0.0014(11) 0.0134(11) 0.0013(10) C13B 0.0261(13) 0.0338(15) 0.0413(17) 0.0037(12) 0.0140(13) 0.0050(11) C14B 0.0334(15) 0.0301(14) 0.0484(18) 0.0000(13) 0.0181(14) 0.0026(12) C15B 0.0234(13) 0.0387(16) 0.0347(16) 0.0005(12) 0.0101(12) 0.0039(11) C16B 0.0291(13) 0.0311(14) 0.0291(15) -0.0027(11) 0.0139(12) 0.0024(11) C20B 0.0251(13) 0.0356(14) 0.0310(15) 0.0004(12) 0.0125(12) 0.0018(11) C21B 0.0241(13) 0.0347(14) 0.0325(15) 0.0020(11) 0.0166(12) 0.0019(11) C22B 0.0212(12) 0.0321(14) 0.0228(13) -0.0020(11) 0.0107(11) -0.0002(10) C23B 0.0259(13) 0.0307(14) 0.0311(15) -0.0025(11) 0.0143(12) -0.0019(10) C24B 0.0236(13) 0.0388(15) 0.0343(16) -0.0052(12) 0.0137(12) -0.0052(11) C25B 0.0325(14) 0.0293(14) 0.0501(18) 0.0007(13) 0.0180(14) 0.0010(11) C26B 0.0221(13) 0.0345(15) 0.0433(17) -0.0018(12) 0.0117(12) -0.0040(11) O1C 0.0339(10) 0.0344(11) 0.0443(12) 0.0016(9) 0.0116(9) -0.0002(8) N11C 0.0300(12) 0.0508(15) 0.0344(13) -0.0013(11) 0.0180(11) 0.0078(11) N21C 0.0291(11) 0.0426(14) 0.0348(13) -0.0028(11) 0.0164(10) -0.0051(10) C1C 0.0276(13) 0.0369(15) 0.0276(15) -0.0003(12) 0.0149(12) -0.0020(11) C10C 0.0297(14) 0.0347(14) 0.0344(15) 0.0017(12) 0.0149(12) 0.0001(11) C11C 0.0311(14) 0.0376(15) 0.0318(15) 0.0000(12) 0.0188(12) 0.0014(11) C12C 0.0265(13) 0.0388(15) 0.0271(14) -0.0005(11) 0.0159(12) 0.0025(11) C13C 0.0320(14) 0.0376(16) 0.0399(17) -0.0025(13) 0.0181(13) 0.0012(12) C14C 0.0406(16) 0.0460(17) 0.0441(18) 0.0013(14) 0.0227(15) 0.0121(13) C15C 0.0265(14) 0.0565(19) 0.0350(16) -0.0017(14) 0.0169(13) -0.0002(13) C16C 0.0316(14) 0.0397(15) 0.0326(16) 0.0038(12) 0.0174(13) 0.0022(12) C20C 0.0281(13) 0.0309(14) 0.0292(14) 0.0021(11) 0.0131(12) -0.0007(11) C21C 0.0285(13) 0.0326(14) 0.0296(15) 0.0009(11) 0.0180(12) 0.0003(11) C22C 0.0242(12) 0.0344(14) 0.0239(14) 0.0012(11) 0.0147(11) 0.0002(10) C23C 0.0267(13) 0.0362(15) 0.0342(15) 0.0048(12) 0.0156(12) 0.0064(11) C24C 0.0322(14) 0.0309(14) 0.0440(17) -0.0039(12) 0.0195(13) -0.0025(11) C25C 0.0255(13) 0.0427(16) 0.0294(15) 0.0047(12) 0.0143(12) 0.0053(11) C26C 0.0276(13) 0.0293(13) 0.0342(15) 0.0018(11) 0.0173(12) 0.0017(11) O1D 0.0347(10) 0.0317(10) 0.0425(12) -0.0001(9) 0.0177(9) 0.0012(8) N11D 0.0245(11) 0.0441(14) 0.0341(13) -0.0043(10) 0.0156(10) -0.0026(10) N21D 0.0268(11) 0.0503(15) 0.0320(13) -0.0024(11) 0.0131(10) -0.0035(10) C1D 0.0294(13) 0.0317(15) 0.0297(15) -0.0038(11) 0.0172(12) 0.0012(11) C10D 0.0287(13) 0.0282(13) 0.0379(16) 0.0005(12) 0.0172(12) 0.0014(11) C11D 0.0330(14) 0.0246(13) 0.0341(15) 0.0001(11) 0.0182(12) -0.0003(11) C12D 0.0292(13) 0.0342(14) 0.0280(14) -0.0027(11) 0.0171(12) -0.0021(11) C13D 0.0294(14) 0.0313(14) 0.0393(16) -0.0043(12) 0.0175(13) -0.0054(11) C14D 0.0287(14) 0.0359(15) 0.0430(17) -0.0009(12) 0.0189(13) 0.0031(11) C15D 0.0311(14) 0.0437(17) 0.0346(16) -0.0079(13) 0.0155(13) -0.0118(12) C16D 0.0394(15) 0.0320(14) 0.0316(16) -0.0014(12) 0.0165(13) -0.0058(12) C20D 0.0277(13) 0.0287(13) 0.0332(15) -0.0046(11) 0.0157(12) -0.0001(10) C21D 0.0286(13) 0.0330(14) 0.0349(15) 0.0000(12) 0.0178(12) -0.0004(11) C22D 0.0239(12) 0.0379(14) 0.0250(14) 0.0005(11) 0.0142(11) 0.0001(11) C23D 0.0282(13) 0.0376(15) 0.0332(15) -0.0021(12) 0.0142(12) 0.0014(11) C24D 0.0342(15) 0.0362(15) 0.0443(17) -0.0039(13) 0.0203(14) -0.0018(12) C25D 0.0262(14) 0.0512(18) 0.0334(16) 0.0077(13) 0.0107(12) 0.0051(12) C26D 0.0330(14) 0.0372(15) 0.0344(16) 0.0066(12) 0.0152(13) 0.0033(12) O1E 0.0276(10) 0.0798(15) 0.0433(12) 0.0058(11) 0.0176(9) 0.0113(10) O3E 0.0316(10) 0.0564(12) 0.0327(11) 0.0041(9) 0.0164(9) 0.0131(9) O5E 0.0365(11) 0.0807(15) 0.0299(12) 0.0062(10) 0.0142(9) 0.0206(10) C1E 0.0273(13) 0.0300(14) 0.0421(17) 0.0020(12) 0.0179(13) 0.0017(11) C2E 0.0253(13) 0.0356(15) 0.0308(15) 0.0058(12) 0.0093(12) 0.0041(11) C3E 0.0331(14) 0.0315(14) 0.0348(16) 0.0029(12) 0.0208(13) 0.0042(11) C4E 0.0252(13) 0.0410(15) 0.0319(16) 0.0030(12) 0.0125(12) 0.0074(11) C5E 0.0315(14) 0.0334(15) 0.0323(16) 0.0020(12) 0.0129(13) 0.0060(11) C6E 0.0302(14) 0.0370(15) 0.0359(16) 0.0019(12) 0.0189(13) 0.0023(11) O1F 0.0246(9) 0.0441(11) 0.0313(10) 0.0006(8) 0.0150(8) 0.0084(8) O3F 0.0231(9) 0.0432(11) 0.0404(11) -0.0033(9) 0.0123(8) 0.0083(8) O5F 0.0246(9) 0.0411(10) 0.0311(11) 0.0002(8) 0.0122(8) 0.0074(8) C1F 0.0230(12) 0.0235(12) 0.0315(15) -0.0012(10) 0.0150(11) -0.0018(10) C2F 0.0211(12) 0.0290(13) 0.0277(14) 0.0001(11) 0.0082(11) -0.0015(10) C3F 0.0208(12) 0.0239(12) 0.0342(15) 0.0005(11) 0.0126(11) 0.0013(10) C4F 0.0246(12) 0.0269(13) 0.0350(16) -0.0026(11) 0.0177(12) 0.0016(10) C5F 0.0242(12) 0.0262(13) 0.0269(14) -0.0001(10) 0.0116(11) -0.0025(10) C6F 0.0190(11) 0.0232(12) 0.0344(15) 0.0003(11) 0.0132(11) 0.0013(9) O1G 0.0328(10) 0.0545(12) 0.0266(10) -0.0025(9) 0.0121(8) -0.0075(9) O3G 0.0284(9) 0.0469(11) 0.0365(11) 0.0001(9) 0.0119(9) -0.0127(8) O5G 0.0267(9) 0.0489(11) 0.0319(10) 0.0006(8) 0.0153(8) -0.0050(8) C1G 0.0262(12) 0.0294(13) 0.0298(15) -0.0001(11) 0.0138(12) 0.0024(10) C2G 0.0294(13) 0.0324(14) 0.0325(15) 0.0025(11) 0.0167(12) -0.0010(11) C3G 0.0256(13) 0.0279(13) 0.0349(16) -0.0005(11) 0.0149(12) -0.0020(10) C4G 0.0252(12) 0.0296(13) 0.0251(14) -0.0020(11) 0.0095(11) 0.0012(10) C5G 0.0253(12) 0.0291(13) 0.0299(15) 0.0014(11) 0.0159(12) 0.0024(10) C6G 0.0193(12) 0.0295(13) 0.0305(15) -0.0020(11) 0.0092(11) -0.0005(10) _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 1.229(3) . ? N11A C14A 1.337(3) . ? N11A C15A 1.339(3) . ? N21A C25A 1.333(3) . ? N21A C24A 1.337(3) . ? C1A C20A 1.477(3) . ? C1A C10A 1.482(3) . ? C10A C11A 1.332(3) . ? C10A H10A 0.9500 . ? C11A C12A 1.460(3) . ? C11A H11A 0.9500 . ? C12A C13A 1.386(3) . ? C12A C16A 1.397(3) . ? C13A C14A 1.384(3) . ? C13A H13A 0.9500 . ? C14A H14A 0.9500 . ? C15A C16A 1.378(3) . ? C15A H15A 0.9500 . ? C16A H16A 0.9500 . ? C20A C21A 1.328(3) . ? C20A H20A 0.9500 . ? C21A C22A 1.473(3) . ? C21A H21A 0.9500 . ? C22A C23A 1.389(3) . ? C22A C26A 1.395(3) . ? C23A C24A 1.385(3) . ? C23A H23A 0.9500 . ? C24A H24A 0.9500 . ? C25A C26A 1.375(3) . ? C25A H25A 0.9500 . ? C26A H26A 0.9500 . ? O1B C1B 1.230(3) . ? N11B C15B 1.335(3) . ? N11B C14B 1.337(3) . ? N21B C24B 1.332(3) . ? N21B C25B 1.338(3) . ? C1B C10B 1.476(3) . ? C1B C20B 1.476(3) . ? C10B C11B 1.328(3) . ? C10B H10B 0.9500 . ? C11B C12B 1.464(3) . ? C11B H11B 0.9500 . ? C12B C13B 1.387(3) . ? C12B C16B 1.389(3) . ? C13B C14B 1.370(3) . ? C13B H13B 0.9500 . ? C14B H14B 0.9500 . ? C15B C16B 1.384(3) . ? C15B H15B 0.9500 . ? C16B H16B 0.9500 . ? C20B C21B 1.323(3) . ? C20B H20B 0.9500 . ? C21B C22B 1.473(3) . ? C21B H21B 0.9500 . ? C22B C23B 1.383(3) . ? C22B C26B 1.389(3) . ? C23B C24B 1.385(3) . ? C23B H23B 0.9500 . ? C24B H24B 0.9500 . ? C25B C26B 1.376(3) . ? C25B H25B 0.9500 . ? C26B H26B 0.9500 . ? O1C C1C 1.217(3) . ? N11C C14C 1.326(3) . ? N11C C15C 1.340(3) . ? N21C C25C 1.331(3) . ? N21C C24C 1.342(3) . ? C1C C20C 1.472(3) . ? C1C C10C 1.489(3) . ? C10C C11C 1.328(3) . ? C10C H10C 0.9500 . ? C11C C12C 1.469(3) . ? C11C H11C 0.9500 . ? C12C C16C 1.385(3) . ? C12C C13C 1.388(4) . ? C13C C14C 1.386(4) . ? C13C H13C 0.9500 . ? C14C H14C 0.9500 . ? C15C C16C 1.377(3) . ? C15C H15C 0.9500 . ? C16C H16C 0.9500 . ? C20C C21C 1.325(3) . ? C20C H20C 0.9500 . ? C21C C22C 1.468(3) . ? C21C H21C 0.9500 . ? C22C C26C 1.382(3) . ? C22C C23C 1.395(3) . ? C23C C24C 1.380(3) . ? C23C H23C 0.9500 . ? C24C H24C 0.9500 . ? C25C C26C 1.385(3) . ? C25C H25C 0.9500 . ? C26C H26C 0.9500 . ? O1D C1D 1.225(3) . ? N11D C15D 1.331(3) . ? N11D C14D 1.339(3) . ? N21D C25D 1.329(3) . ? N21D C24D 1.337(3) . ? C1D C10D 1.466(3) . ? C1D C20D 1.475(3) . ? C10D C11D 1.324(3) . ? C10D H10D 0.9500 . ? C11D C12D 1.472(3) . ? C11D H11D 0.9500 . ? C12D C16D 1.386(3) . ? C12D C13D 1.388(3) . ? C13D C14D 1.377(3) . ? C13D H13D 0.9500 . ? C14D H14D 0.9500 . ? C15D C16D 1.381(3) . ? C15D H15D 0.9500 . ? C16D H16D 0.9500 . ? C20D C21D 1.320(3) . ? C20D H20D 0.9500 . ? C21D C22D 1.466(3) . ? C21D H21D 0.9500 . ? C22D C26D 1.386(3) . ? C22D C23D 1.394(4) . ? C23D C24D 1.372(3) . ? C23D H23D 0.9500 . ? C24D H24D 0.9500 . ? C25D C26D 1.382(3) . ? C25D H25D 0.9500 . ? C26D H26D 0.9500 . ? O1E C1E 1.354(3) . ? O1E H1 1.0363 . ? O3E C3E 1.373(3) . ? O3E H2 1.0503 . ? O5E C5E 1.375(3) . ? O5E H3 1.0635 . ? C1E C2E 1.389(4) . ? C1E C6E 1.388(4) . ? C2E C3E 1.391(3) . ? C2E H2E 0.9500 . ? C3E C4E 1.392(3) . ? C4E C5E 1.397(4) . ? C4E H4E 0.9500 . ? C5E C6E 1.376(3) . ? C6E H6E 0.9500 . ? O1F C1F 1.367(3) . ? O1F H4 0.8944 . ? O3F C3F 1.363(3) . ? O3F H5 0.9323 . ? O5F C5F 1.367(3) . ? O5F H6 0.8728 . ? C1F C2F 1.383(3) . ? C1F C6F 1.391(3) . ? C2F C3F 1.391(3) . ? C2F H2F 0.9500 . ? C3F C4F 1.375(3) . ? C4F C5F 1.386(3) . ? C4F H4F 0.9500 . ? C5F C6F 1.394(3) . ? C6F H6F 0.9500 . ? O1G C1G 1.367(3) . ? O1G H7 1.0538 . ? O3G C3G 1.376(3) . ? O3G H8 1.0706 . ? O5G C5G 1.366(3) . ? O5G H9 0.8695 . ? C1G C2G 1.387(3) . ? C1G C6G 1.392(3) . ? C2G C3G 1.387(4) . ? C2G H2G 0.9500 . ? C3G C4G 1.390(3) . ? C4G C5G 1.385(3) . ? C4G H4G 0.9500 . ? C5G C6G 1.391(3) . ? C6G H6G 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 C14A N11A C15A 116.8(2) . . ? C25A N21A C24A 116.5(2) . . ? O1A C1A C20A 121.3(2) . . ? O1A C1A C10A 121.2(2) . . ? C20A C1A C10A 117.5(2) . . ? C11A C10A C1A 121.7(2) . . ? C11A C10A H10A 119.2 . . ? C1A C10A H10A 119.2 . . ? C10A C11A C12A 126.6(2) . . ? C10A C11A H11A 116.7 . . ? C12A C11A H11A 116.7 . . ? C13A C12A C16A 116.6(2) . . ? C13A C12A C11A 119.7(2) . . ? C16A C12A C11A 123.6(2) . . ? C14A C13A C12A 119.7(2) . . ? C14A C13A H13A 120.1 . . ? C12A C13A H13A 120.1 . . ? N11A C14A C13A 123.6(2) . . ? N11A C14A H14A 118.2 . . ? C13A C14A H14A 118.2 . . ? N11A C15A C16A 123.2(2) . . ? N11A C15A H15A 118.4 . . ? C16A C15A H15A 118.4 . . ? C15A C16A C12A 120.0(2) . . ? C15A C16A H16A 120.0 . . ? C12A C16A H16A 120.0 . . ? C21A C20A C1A 121.4(2) . . ? C21A C20A H20A 119.3 . . ? C1A C20A H20A 119.3 . . ? C20A C21A C22A 127.1(2) . . ? C20A C21A H21A 116.4 . . ? C22A C21A H21A 116.4 . . ? C23A C22A C26A 117.0(2) . . ? C23A C22A C21A 119.5(2) . . ? C26A C22A C21A 123.5(2) . . ? C24A C23A C22A 119.6(2) . . ? C24A C23A H23A 120.2 . . ? C22A C23A H23A 120.2 . . ? N21A C24A C23A 123.4(2) . . ? N21A C24A H24A 118.3 . . ? C23A C24A H24A 118.3 . . ? N21A C25A C26A 124.4(2) . . ? N21A C25A H25A 117.8 . . ? C26A C25A H25A 117.8 . . ? C25A C26A C22A 119.1(2) . . ? C25A C26A H26A 120.5 . . ? C22A C26A H26A 120.5 . . ? C15B N11B C14B 117.1(2) . . ? C24B N21B C25B 116.6(2) . . ? O1B C1B C10B 121.8(2) . . ? O1B C1B C20B 121.0(2) . . ? C10B C1B C20B 117.2(2) . . ? C11B C10B C1B 122.7(2) . . ? C11B C10B H10B 118.6 . . ? C1B C10B H10B 118.6 . . ? C10B C11B C12B 126.5(2) . . ? C10B C11B H11B 116.7 . . ? C12B C11B H11B 116.7 . . ? C13B C12B C16B 116.9(2) . . ? C13B C12B C11B 123.2(2) . . ? C16B C12B C11B 119.9(2) . . ? C14B C13B C12B 120.1(2) . . ? C14B C13B H13B 119.9 . . ? C12B C13B H13B 119.9 . . ? N11B C14B C13B 123.3(2) . . ? N11B C14B H14B 118.4 . . ? C13B C14B H14B 118.4 . . ? N11B C15B C16B 123.3(2) . . ? N11B C15B H15B 118.3 . . ? C16B C15B H15B 118.3 . . ? C15B C16B C12B 119.4(2) . . ? C15B C16B H16B 120.3 . . ? C12B C16B H16B 120.3 . . ? C21B C20B C1B 121.5(2) . . ? C21B C20B H20B 119.2 . . ? C1B C20B H20B 119.2 . . ? C20B C21B C22B 126.9(2) . . ? C20B C21B H21B 116.5 . . ? C22B C21B H21B 116.5 . . ? C23B C22B C26B 117.3(2) . . ? C23B C22B C21B 119.5(2) . . ? C26B C22B C21B 123.2(2) . . ? C22B C23B C24B 119.6(2) . . ? C22B C23B H23B 120.2 . . ? C24B C23B H23B 120.2 . . ? N21B C24B C23B 123.3(2) . . ? N21B C24B H24B 118.3 . . ? C23B C24B H24B 118.3 . . ? N21B C25B C26B 124.1(2) . . ? N21B C25B H25B 118.0 . . ? C26B C25B H25B 118.0 . . ? C25B C26B C22B 119.0(2) . . ? C25B C26B H26B 120.5 . . ? C22B C26B H26B 120.5 . . ? C14C N11C C15C 116.5(2) . . ? C25C N21C C24C 116.4(2) . . ? O1C C1C C20C 122.6(2) . . ? O1C C1C C10C 121.3(2) . . ? C20C C1C C10C 116.2(2) . . ? C11C C10C C1C 122.2(2) . . ? C11C C10C H10C 118.9 . . ? C1C C10C H10C 118.9 . . ? C10C C11C C12C 126.6(2) . . ? C10C C11C H11C 116.7 . . ? C12C C11C H11C 116.7 . . ? C16C C12C C13C 117.0(2) . . ? C16C C12C C11C 119.8(2) . . ? C13C C12C C11C 123.2(2) . . ? C14C C13C C12C 119.0(3) . . ? C14C C13C H13C 120.5 . . ? C12C C13C H13C 120.5 . . ? N11C C14C C13C 124.2(3) . . ? N11C C14C H14C 117.9 . . ? C13C C14C H14C 117.9 . . ? N11C C15C C16C 123.4(3) . . ? N11C C15C H15C 118.3 . . ? C16C C15C H15C 118.3 . . ? C15C C16C C12C 119.9(3) . . ? C15C C16C H16C 120.0 . . ? C12C C16C H16C 120.0 . . ? C21C C20C C1C 121.3(2) . . ? C21C C20C H20C 119.4 . . ? C1C C20C H20C 119.4 . . ? C20C C21C C22C 127.0(2) . . ? C20C C21C H21C 116.5 . . ? C22C C21C H21C 116.5 . . ? C26C C22C C23C 117.3(2) . . ? C26C C22C C21C 119.5(2) . . ? C23C C22C C21C 123.3(2) . . ? C24C C23C C22C 119.1(2) . . ? C24C C23C H23C 120.5 . . ? C22C C23C H23C 120.5 . . ? N21C C24C C23C 123.9(2) . . ? N21C C24C H24C 118.1 . . ? C23C C24C H24C 118.1 . . ? N21C C25C C26C 123.9(2) . . ? N21C C25C H25C 118.1 . . ? C26C C25C H25C 118.1 . . ? C25C C26C C22C 119.5(2) . . ? C25C C26C H26C 120.2 . . ? C22C C26C H26C 120.2 . . ? C15D N11D C14D 116.3(2) . . ? C25D N21D C24D 117.3(2) . . ? O1D C1D C10D 122.1(2) . . ? O1D C1D C20D 121.0(2) . . ? C10D C1D C20D 116.9(2) . . ? C11D C10D C1D 122.7(2) . . ? C11D C10D H10D 118.6 . . ? C1D C10D H10D 118.6 . . ? C10D C11D C12D 126.6(2) . . ? C10D C11D H11D 116.7 . . ? C12D C11D H11D 116.7 . . ? C16D C12D C13D 117.0(2) . . ? C16D C12D C11D 119.8(2) . . ? C13D C12D C11D 123.2(2) . . ? C14D C13D C12D 119.1(2) . . ? C14D C13D H13D 120.4 . . ? C12D C13D H13D 120.4 . . ? N11D C14D C13D 124.2(2) . . ? N11D C14D H14D 117.9 . . ? C13D C14D H14D 117.9 . . ? N11D C15D C16D 123.5(2) . . ? N11D C15D H15D 118.3 . . ? C16D C15D H15D 118.3 . . ? C15D C16D C12D 119.9(2) . . ? C15D C16D H16D 120.1 . . ? C12D C16D H16D 120.1 . . ? C21D C20D C1D 122.7(2) . . ? C21D C20D H20D 118.7 . . ? C1D C20D H20D 118.7 . . ? C20D C21D C22D 127.3(2) . . ? C20D C21D H21D 116.3 . . ? C22D C21D H21D 116.3 . . ? C26D C22D C23D 117.1(2) . . ? C26D C22D C21D 119.6(2) . . ? C23D C22D C21D 123.3(2) . . ? C24D C23D C22D 119.2(2) . . ? C24D C23D H23D 120.4 . . ? C22D C23D H23D 120.4 . . ? N21D C24D C23D 123.7(3) . . ? N21D C24D H24D 118.2 . . ? C23D C24D H24D 118.2 . . ? N21D C25D C26D 123.0(2) . . ? N21D C25D H25D 118.5 . . ? C26D C25D H25D 118.5 . . ? C25D C26D C22D 119.7(2) . . ? C25D C26D H26D 120.1 . . ? C22D C26D H26D 120.1 . . ? C1E O1E H1 114.1 . . ? C3E O3E H2 109.7 . . ? C5E O5E H3 115.9 . . ? O1E C1E C2E 123.5(2) . . ? O1E C1E C6E 115.3(2) . . ? C2E C1E C6E 121.1(2) . . ? C1E C2E C3E 118.5(2) . . ? C1E C2E H2E 120.7 . . ? C3E C2E H2E 120.7 . . ? O3E C3E C4E 121.5(2) . . ? O3E C3E C2E 117.1(2) . . ? C4E C3E C2E 121.5(2) . . ? C3E C4E C5E 118.2(2) . . ? C3E C4E H4E 120.9 . . ? C5E C4E H4E 120.9 . . ? O5E C5E C6E 116.8(2) . . ? O5E C5E C4E 121.8(2) . . ? C6E C5E C4E 121.3(2) . . ? C5E C6E C1E 119.3(2) . . ? C5E C6E H6E 120.4 . . ? C1E C6E H6E 120.4 . . ? C1F O1F H4 108.7 . . ? C3F O3F H5 113.3 . . ? C5F O5F H6 111.4 . . ? O1F C1F C2F 117.8(2) . . ? O1F C1F C6F 121.6(2) . . ? C2F C1F C6F 120.7(2) . . ? C1F C2F C3F 119.4(2) . . ? C1F C2F H2F 120.3 . . ? C3F C2F H2F 120.3 . . ? O3F C3F C4F 117.9(2) . . ? O3F C3F C2F 121.1(2) . . ? C4F C3F C2F 121.1(2) . . ? C3F C4F C5F 119.0(2) . . ? C3F C4F H4F 120.5 . . ? C5F C4F H4F 120.5 . . ? O5F C5F C4F 117.9(2) . . ? O5F C5F C6F 120.9(2) . . ? C4F C5F C6F 121.2(2) . . ? C1F C6F C5F 118.6(2) . . ? C1F C6F H6F 120.7 . . ? C5F C6F H6F 120.7 . . ? C1G O1G H7 108.4 . . ? C3G O3G H8 111.3 . . ? C5G O5G H9 109.5 . . ? O1G C1G C2G 118.2(2) . . ? O1G C1G C6G 121.0(2) . . ? C2G C1G C6G 120.8(2) . . ? C3G C2G C1G 119.0(2) . . ? C3G C2G H2G 120.5 . . ? C1G C2G H2G 120.5 . . ? O3G C3G C2G 117.7(2) . . ? O3G C3G C4G 121.0(2) . . ? C2G C3G C4G 121.3(2) . . ? C5G C4G C3G 118.8(2) . . ? C5G C4G H4G 120.6 . . ? C3G C4G H4G 120.6 . . ? O5G C5G C4G 117.3(2) . . ? O5G C5G C6G 121.7(2) . . ? C4G C5G C6G 121.1(2) . . ? C5G C6G C1G 119.1(2) . . ? C5G C6G H6G 120.5 . . ? C1G C6G H6G 120.5 . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.549 _refine_diff_density_min -0.334 _refine_diff_density_rms 0.057 data_6 _database_code_depnum_ccdc_archive 'CCDC 793078' #TrackingRef '- kb1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (1,5-bis(4-pyridyl)-1,4-pentadiene-3-one).(phloroglucinol) ; _chemical_name_common (1,5-bis(4-pyridyl)-1,4-pentadiene-3-one).(phloroglucinol) _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H18 N2 O4' _chemical_formula_weight 362.37 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 8.6268(9) _cell_length_b 9.6019(10) _cell_length_c 12.1252(13) _cell_angle_alpha 76.149(3) _cell_angle_beta 88.030(3) _cell_angle_gamma 67.701(3) _cell_volume 900.46(16) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3341 _cell_measurement_theta_min 1.73 _cell_measurement_theta_max 25.49 _exptl_crystal_description plates _exptl_crystal_colour orange _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.337 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 380 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.981 _exptl_absorpt_correction_T_max 0.987 _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 CCD APEX-2' _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 11171 _diffrn_reflns_av_R_equivalents 0.0254 _diffrn_reflns_av_sigmaI/netI 0.0252 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 25.49 _reflns_number_total 3341 _reflns_number_gt 2424 _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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3341 _refine_ls_number_parameters 298 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0617 _refine_ls_R_factor_gt 0.0408 _refine_ls_wR_factor_ref 0.1416 _refine_ls_wR_factor_gt 0.1282 _refine_ls_goodness_of_fit_ref 0.978 _refine_ls_restrained_S_all 0.978 _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 N11 N 0.24410(17) 0.14758(17) 0.01012(12) 0.0611(4) Uani 1 1 d . . . N21 N 1.27553(16) -0.41559(16) 0.81757(12) 0.0577(4) Uani 1 1 d . . . O10 O 0.5899(11) 0.2100(11) 0.4971(9) 0.069(3) Uani 0.50 1 d P A 1 C10 C 0.6543(17) 0.0853(11) 0.4726(15) 0.051(2) Uani 0.50 1 d P A 1 C11 C 0.5903(6) 0.0653(7) 0.3688(4) 0.0491(11) Uani 0.50 1 d P A 1 H11 H 0.6483 -0.0263 0.3467 0.059 Uiso 0.50 1 calc PR A 1 C12 C 0.4532(4) 0.1707(4) 0.3036(3) 0.0430(7) Uani 0.50 1 d P A 1 H12 H 0.3990 0.2619 0.3270 0.052 Uiso 0.50 1 calc PR A 1 C13 C 0.3800(6) 0.1603(6) 0.2025(4) 0.0404(9) Uani 0.50 1 d P A 1 C14 C 0.2700(5) 0.2947(5) 0.1257(4) 0.0549(11) Uani 0.50 1 d P A 1 H14 H 0.2311 0.3925 0.1406 0.066 Uiso 0.50 1 calc PR A 1 O10A O 0.5817(11) 0.2412(13) 0.5325(6) 0.0676(15) Uani 0.50 1 d P A 2 C10A C 0.6277(13) 0.1377(9) 0.4818(10) 0.052(5) Uani 0.50 1 d P A 2 C11A C 0.5324(5) 0.1548(5) 0.3811(3) 0.0572(10) Uani 0.50 1 d P A 2 H11A H 0.4419 0.2489 0.3567 0.069 Uiso 0.50 1 calc PR A 2 C12A C 0.5563(6) 0.0574(6) 0.3213(4) 0.0496(11) Uani 0.50 1 d P A 2 H12A H 0.6443 -0.0387 0.3440 0.060 Uiso 0.50 1 calc PR A 2 C13A C 0.4491(5) 0.0898(5) 0.2152(4) 0.0452(9) Uani 0.50 1 d P A 2 C14A C 0.3561(8) 0.2390(7) 0.1540(4) 0.0598(12) Uani 0.50 1 d P A 2 H14A H 0.3638 0.3223 0.1766 0.072 Uiso 0.50 1 calc PR A 2 C15 C 0.2323(4) 0.2732(3) 0.0427(2) 0.0961(8) Uani 1 1 d . . . H15 H 0.1829 0.3642 -0.0137 0.115 Uiso 1 1 d R A . C16 C 0.33790(19) 0.0126(2) 0.07712(14) 0.0548(4) Uani 1 1 d U . . H16 H 0.3467 -0.0771 0.0564 0.066 Uiso 1 1 calc R A . C17 C 0.4230(2) -0.0029(3) 0.17522(15) 0.0690(5) Uani 1 1 d U A . H17 H 0.4964 -0.0968 0.2199 0.083 Uiso 1 1 d R . . C21 C 0.7870(2) -0.0236(2) 0.53235(15) 0.0593(5) Uani 1 1 d . . . H21 H 0.8319 -0.1125 0.5050 0.071 Uiso 1 1 d R A . C22 C 0.86780(18) -0.02865(19) 0.62463(13) 0.0499(4) Uani 1 1 d . A . H22 H 0.8328 0.0618 0.6502 0.060 Uiso 1 1 calc R . . C23 C 1.00680(17) -0.16255(18) 0.69046(13) 0.0448(4) Uani 1 1 d . . . C24 C 1.0622(2) -0.3078(2) 0.66758(16) 0.0640(5) Uani 1 1 d . A . H24 H 1.0099 -0.3234 0.6084 0.077 Uiso 1 1 calc R . . C25 C 1.1937(2) -0.4280(2) 0.73216(16) 0.0667(5) Uani 1 1 d . . . H25 H 1.2278 -0.5243 0.7152 0.080 Uiso 1 1 calc R A . C26 C 1.22158(19) -0.2771(2) 0.84116(14) 0.0552(4) Uani 1 1 d . . . H26 H 1.2759 -0.2656 0.9013 0.066 Uiso 1 1 calc R A . C27 C 1.08950(19) -0.14995(19) 0.78116(14) 0.0511(4) Uani 1 1 d . A . H27 H 1.0559 -0.0558 0.8015 0.061 Uiso 1 1 calc R . . O1 O 0.27353(16) 0.46622(16) 0.49117(10) 0.0762(4) Uani 1 1 d . . . H1O H 0.3811 0.4030 0.4980 0.114 Uiso 1 1 d R . . O2 O -0.15551(13) 0.79835(14) 0.21378(10) 0.0635(4) Uani 1 1 d . . . H2O H -0.1780 0.8230 0.1321 0.095 Uiso 1 1 d R . . O3 O 0.40951(13) 0.64422(13) 0.10985(9) 0.0610(4) Uani 1 1 d . . . H3O H 0.5140 0.5730 0.1361 0.092 Uiso 1 1 d R . . C1 C 0.2300(2) 0.55366(18) 0.38189(13) 0.0511(4) Uani 1 1 d . . . C2 C 0.0610(2) 0.63499(18) 0.35155(13) 0.0520(4) Uani 1 1 d . . . H2 H -0.0185 0.6329 0.4050 0.062 Uiso 1 1 calc R . . C3 C 0.01223(18) 0.71938(17) 0.24057(14) 0.0476(4) Uani 1 1 d . . . C4 C 0.12960(19) 0.72283(17) 0.16039(13) 0.0498(4) Uani 1 1 d . . . H4 H 0.0953 0.7802 0.0858 0.060 Uiso 1 1 calc R . . C5 C 0.29848(19) 0.64020(17) 0.19209(13) 0.0464(4) Uani 1 1 d . . . C6 C 0.34974(19) 0.55771(17) 0.30408(13) 0.0493(4) Uani 1 1 d . . . H6 H 0.4633 0.5058 0.3264 0.059 Uiso 1 1 calc R . . 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 N11 0.0565(8) 0.0637(9) 0.0570(9) -0.0112(7) 0.0008(7) -0.0184(7) N21 0.0487(8) 0.0562(9) 0.0539(9) -0.0027(7) -0.0007(7) -0.0109(6) O10 0.069(3) 0.056(6) 0.066(4) -0.006(5) -0.023(3) -0.010(4) C10 0.042(3) 0.040(6) 0.058(3) 0.005(4) 0.002(2) -0.013(4) C11 0.036(2) 0.056(3) 0.048(3) -0.009(3) -0.005(2) -0.011(2) C12 0.0396(15) 0.0449(18) 0.0387(17) -0.0036(13) -0.0091(14) -0.0129(15) C13 0.037(2) 0.029(3) 0.042(2) 0.004(2) -0.006(2) -0.0055(19) C14 0.053(2) 0.043(2) 0.055(3) 0.003(2) -0.023(2) -0.0089(18) O10A 0.061(2) 0.060(3) 0.067(4) -0.015(2) -0.022(3) -0.0059(19) C10A 0.045(6) 0.039(9) 0.056(7) 0.022(8) -0.025(5) -0.018(6) C11A 0.048(2) 0.052(2) 0.057(2) -0.002(2) -0.0096(19) -0.0082(18) C12A 0.042(2) 0.051(2) 0.045(3) -0.001(2) -0.003(2) -0.0121(19) C13A 0.044(2) 0.046(3) 0.040(2) -0.003(2) -0.0009(19) -0.0144(18) C14A 0.075(3) 0.054(4) 0.049(3) -0.011(3) -0.020(3) -0.023(3) C15 0.145(2) 0.0672(14) 0.0800(17) -0.0158(12) 0.0313(16) -0.0487(15) C16 0.0493(9) 0.0593(10) 0.0538(10) -0.0146(8) -0.0033(8) -0.0177(7) C17 0.0605(11) 0.1018(16) 0.0487(11) -0.0101(10) -0.0003(9) -0.0402(11) C21 0.0515(9) 0.0773(12) 0.0470(10) -0.0069(9) -0.0025(8) -0.0269(9) C22 0.0419(8) 0.0589(10) 0.0456(9) -0.0061(7) -0.0020(7) -0.0192(7) C23 0.0386(7) 0.0521(9) 0.0417(9) -0.0087(7) 0.0025(6) -0.0168(7) C24 0.0625(10) 0.0642(11) 0.0643(12) -0.0229(9) -0.0120(9) -0.0175(9) C25 0.0624(11) 0.0554(10) 0.0760(13) -0.0211(9) -0.0055(10) -0.0121(8) C26 0.0475(9) 0.0682(11) 0.0453(9) -0.0114(8) -0.0037(7) -0.0179(8) C27 0.0470(8) 0.0556(9) 0.0484(9) -0.0140(7) -0.0029(7) -0.0158(7) O1 0.0664(8) 0.0911(10) 0.0423(7) 0.0009(6) -0.0018(6) -0.0087(7) O2 0.0443(6) 0.0709(8) 0.0597(7) -0.0147(6) -0.0029(5) -0.0052(5) O3 0.0469(6) 0.0610(7) 0.0530(7) 0.0029(5) 0.0017(5) -0.0065(5) C1 0.0559(9) 0.0493(9) 0.0391(9) -0.0070(7) -0.0050(7) -0.0120(7) C2 0.0524(9) 0.0533(9) 0.0459(10) -0.0142(8) 0.0045(7) -0.0141(7) C3 0.0438(8) 0.0431(8) 0.0505(9) -0.0146(7) -0.0032(7) -0.0085(6) C4 0.0504(9) 0.0450(9) 0.0439(9) -0.0057(7) -0.0059(7) -0.0097(7) C5 0.0471(8) 0.0408(8) 0.0461(9) -0.0095(7) 0.0008(7) -0.0118(6) C6 0.0460(8) 0.0460(9) 0.0477(9) -0.0084(7) -0.0063(7) -0.0097(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 N11 C16 1.319(2) . ? N11 C15 1.324(3) . ? N21 C25 1.326(2) . ? N21 C26 1.331(2) . ? O10 C10 1.218(12) . ? C10 C21 1.309(13) . ? C10 C11 1.474(18) . ? C11 C12 1.350(6) . ? C11 H11 0.9300 . ? C12 C13 1.439(5) . ? C12 H12 0.9300 . ? C13 C14 1.410(5) . ? C13 C17 1.582(5) . ? C14 C15 1.156(5) . ? C14 H14 0.9300 . ? O10A C10A 1.226(12) . ? C10A C11A 1.436(11) . ? C10A C21 1.628(8) . ? C11A C12A 1.269(7) . ? C11A H11A 0.9300 . ? C12A C13A 1.510(6) . ? C12A H12A 0.9300 . ? C13A C17 1.202(4) . ? C13A C14A 1.381(6) . ? C14A C15 1.641(5) . ? C14A H14A 0.9300 . ? C15 H15 0.9296 . ? C16 C17 1.367(2) . ? C16 H16 0.9300 . ? C17 H17 0.9294 . ? C21 C22 1.320(2) . ? C21 H21 0.9297 . ? C22 C23 1.460(2) . ? C22 H22 0.9300 . ? C23 C27 1.384(2) . ? C23 C24 1.386(2) . ? C24 C25 1.366(2) . ? C24 H24 0.9300 . ? C25 H25 0.9300 . ? C26 C27 1.376(2) . ? C26 H26 0.9300 . ? C27 H27 0.9300 . ? O1 C1 1.3653(19) . ? O1 H1O 0.8889 . ? O2 C3 1.3624(17) . ? O2 H2O 0.9702 . ? O3 C5 1.3628(19) . ? O3 H3O 0.9107 . ? C1 C6 1.380(2) . ? C1 C2 1.380(2) . ? C2 C3 1.379(2) . ? C2 H2 0.9300 . ? C3 C4 1.383(2) . ? C4 C5 1.384(2) . ? C4 H4 0.9300 . ? C5 C6 1.388(2) . ? C6 H6 0.9300 . ? 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 N11 C15 116.67(18) . . ? C25 N21 C26 116.58(14) . . ? O10 C10 C21 120.2(17) . . ? O10 C10 C11 118.7(13) . . ? C21 C10 C11 120.8(9) . . ? C12 C11 C10 124.4(6) . . ? C12 C11 H11 117.8 . . ? C10 C11 H11 117.8 . . ? C11 C12 C13 128.4(4) . . ? C11 C12 H12 115.8 . . ? C13 C12 H12 115.8 . . ? C14 C13 C12 120.9(4) . . ? C14 C13 C17 118.7(4) . . ? C12 C13 C17 120.3(4) . . ? C15 C14 C13 114.4(4) . . ? C15 C14 H14 122.8 . . ? C13 C14 H14 122.8 . . ? O10A C10A C11A 119.4(8) . . ? O10A C10A C21 120.6(9) . . ? C11A C10A C21 119.8(7) . . ? C12A C11A C10A 128.0(6) . . ? C12A C11A H11A 116.0 . . ? C10A C11A H11A 116.0 . . ? C11A C12A C13A 123.3(4) . . ? C11A C12A H12A 118.4 . . ? C13A C12A H12A 118.4 . . ? C17 C13A C14A 110.3(4) . . ? C17 C13A C12A 127.5(4) . . ? C14A C13A C12A 122.0(4) . . ? C13A C14A C15 121.7(4) . . ? C13A C14A H14A 119.2 . . ? C15 C14A H14A 119.2 . . ? C14 C15 N11 134.1(3) . . ? N11 C15 C14A 114.5(3) . . ? C14 C15 H15 112.9 . . ? N11 C15 H15 113.0 . . ? C14A C15 H15 129.3 . . ? N11 C16 C17 123.81(18) . . ? N11 C16 H16 118.1 . . ? C17 C16 H16 118.1 . . ? C13A C17 C16 132.1(3) . . ? C16 C17 C13 110.9(2) . . ? C13A C17 H17 102.1 . . ? C16 C17 H17 124.5 . . ? C13 C17 H17 124.5 . . ? C10 C21 C22 131.0(7) . . ? C22 C21 C10A 115.7(4) . . ? C10 C21 H21 114.4 . . ? C22 C21 H21 114.6 . . ? C10A C21 H21 129.7 . . ? C21 C22 C23 126.30(17) . . ? C21 C22 H22 116.8 . . ? C23 C22 H22 116.8 . . ? C27 C23 C24 116.39(14) . . ? C27 C23 C22 120.78(14) . . ? C24 C23 C22 122.83(14) . . ? C25 C24 C23 119.83(16) . . ? C25 C24 H24 120.1 . . ? C23 C24 H24 120.1 . . ? N21 C25 C24 123.95(16) . . ? N21 C25 H25 118.0 . . ? C24 C25 H25 118.0 . . ? N21 C26 C27 123.37(15) . . ? N21 C26 H26 118.3 . . ? C27 C26 H26 118.3 . . ? C26 C27 C23 119.84(15) . . ? C26 C27 H27 120.1 . . ? C23 C27 H27 120.1 . . ? C1 O1 H1O 110.2 . . ? C3 O2 H2O 109.9 . . ? C5 O3 H3O 110.3 . . ? O1 C1 C6 121.39(13) . . ? O1 C1 C2 117.31(15) . . ? C6 C1 C2 121.29(14) . . ? C3 C2 C1 118.83(15) . . ? C3 C2 H2 120.6 . . ? C1 C2 H2 120.6 . . ? O2 C3 C2 117.19(14) . . ? O2 C3 C4 121.80(14) . . ? C2 C3 C4 121.01(14) . . ? C3 C4 C5 119.44(14) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? O3 C5 C4 117.48(13) . . ? O3 C5 C6 122.31(13) . . ? C4 C5 C6 120.21(15) . . ? C1 C6 C5 119.16(14) . . ? C1 C6 H6 120.4 . . ? C5 C6 H6 120.4 . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.49 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.156 _refine_diff_density_min -0.172 _refine_diff_density_rms 0.030 data_7 _database_code_depnum_ccdc_archive 'CCDC 793079' #TrackingRef '- kb1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2(1,5-bis(4-pyridyl)-1,4-pentadiene-3-one).2(methoxyresorcinol).(H2O) ; _chemical_name_common ;2(1,5-bis(4-pyridyl)-1,4-pentadiene-3- one).2(methoxyresorcinol).(H2O) ; _chemical_melting_point ? _chemical_formula_moiety 'C15 H12 N2 O, C7 H8 O3,0.25(H2 O)' _chemical_formula_sum 'C22 H21 N2 O4.25' _chemical_formula_weight 381.41 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 12.091(2) _cell_length_b 14.993(3) _cell_length_c 22.115(4) _cell_angle_alpha 90.00 _cell_angle_beta 97.250(5) _cell_angle_gamma 90.00 _cell_volume 3977.0(13) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3162 _cell_measurement_theta_min 1.86 _cell_measurement_theta_max 25.00 _exptl_crystal_description block _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.287 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1624 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.987 _exptl_absorpt_correction_T_max 0.989 _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 CCD Apex-2' _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 20559 _diffrn_reflns_av_R_equivalents 0.0391 _diffrn_reflns_av_sigmaI/netI 0.0254 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3162 _reflns_number_gt 2008 _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. The water molecule exhibited high thermal parameters, therefore platon squeze option was used in the final refinement. DELU $C was also used in the final refinement. ; _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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3162 _refine_ls_number_parameters 254 _refine_ls_number_restraints 41 _refine_ls_R_factor_all 0.1168 _refine_ls_R_factor_gt 0.0808 _refine_ls_wR_factor_ref 0.2245 _refine_ls_wR_factor_gt 0.2041 _refine_ls_goodness_of_fit_ref 1.364 _refine_ls_restrained_S_all 1.380 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.001 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 O10 O 0.0849(3) 0.6206(3) 0.18975(16) 0.1353(13) Uani 1 1 d . . . N11 N -0.2403(3) 0.4224(2) -0.05752(16) 0.0939(10) Uani 1 1 d . . . N21 N 0.4220(3) 0.3597(2) 0.41081(13) 0.0865(9) Uani 1 1 d . . . C10 C 0.0834(4) 0.5396(3) 0.1870(2) 0.1015(12) Uani 1 1 d U . . C11 C -0.1765(4) 0.3720(3) -0.0188(2) 0.1021(13) Uani 1 1 d U . . H11 H -0.1746 0.3110 -0.0263 0.122 Uiso 1 1 calc R . . C12 C -0.1133(3) 0.4046(2) 0.0314(2) 0.0973(12) Uani 1 1 d U . . H12 H -0.0705 0.3660 0.0577 0.117 Uiso 1 1 calc R . . C13 C -0.1125(3) 0.4944(2) 0.04336(19) 0.0825(10) Uani 1 1 d U . . C14 C -0.1809(3) 0.5466(3) 0.0026(2) 0.0891(10) Uani 1 1 d U . . H14 H -0.1853 0.6077 0.0091 0.107 Uiso 1 1 calc R . . C15 C -0.2421(3) 0.5088(3) -0.0473(2) 0.0985(12) Uani 1 1 d U . . H15 H -0.2860 0.5452 -0.0747 0.118 Uiso 1 1 calc R . . C16 C -0.0477(3) 0.5362(3) 0.0945(2) 0.0970(12) Uani 1 1 d U . . H16 H -0.0500 0.5981 0.0967 0.116 Uiso 1 1 calc R . . C17 C 0.0154(3) 0.4936(3) 0.1390(2) 0.0981(12) Uani 1 1 d U . . H17 H 0.0154 0.4316 0.1391 0.118 Uiso 1 1 calc R . . C21 C 0.4158(3) 0.4465(3) 0.41038(19) 0.0998(13) Uani 1 1 d U . . H21 H 0.4616 0.4779 0.4399 0.120 Uiso 1 1 calc R . . C22 C 0.3457(3) 0.4940(3) 0.36902(19) 0.0974(12) Uani 1 1 d U . . H22 H 0.3453 0.5560 0.3708 0.117 Uiso 1 1 calc R . . C23 C 0.2766(3) 0.4508(3) 0.32530(16) 0.0826(10) Uani 1 1 d U . . C24 C 0.2801(3) 0.3600(3) 0.32688(14) 0.0839(10) Uani 1 1 d U . . H24 H 0.2321 0.3273 0.2990 0.101 Uiso 1 1 calc R . . C25 C 0.3538(3) 0.3161(2) 0.36919(15) 0.0860(10) Uani 1 1 d U . . H25 H 0.3559 0.2541 0.3686 0.103 Uiso 1 1 calc R . . C26 C 0.2075(4) 0.4995(4) 0.2759(3) 0.1295(17) Uani 1 1 d U . . H26 H 0.2119 0.5609 0.2818 0.155 Uiso 1 1 calc R . . C27 C 0.1495(4) 0.4814(4) 0.2319(2) 0.136(2) Uani 1 1 d U . . H27 H 0.1435 0.4207 0.2234 0.163 Uiso 1 1 calc R . . O31 O -0.1152(2) 0.1589(2) 0.15126(12) 0.1001(9) Uani 1 1 d . . . H31O H -0.1667 0.1375 0.1228 0.150 Uiso 1 1 d R . . O32 O 0.2470(2) 0.26755(18) 0.19206(10) 0.0906(8) Uani 1 1 d . . . O33 O 0.09655(18) 0.21270(16) -0.01454(9) 0.0792(7) Uani 1 1 d . . . H33O H 0.0517 0.1985 -0.0363 0.119 Uiso 1 1 d R . . C31 C -0.0214(3) 0.1876(2) 0.12875(15) 0.0657(8) Uani 1 1 d U . . C32 C 0.0662(3) 0.2169(2) 0.16892(14) 0.0736(8) Uani 1 1 d U . . H32 H 0.0604 0.2191 0.2104 0.088 Uiso 1 1 calc R . . C33 C 0.1639(3) 0.2433(2) 0.14724(13) 0.0638(7) Uani 1 1 d U . . C34 C 0.1733(2) 0.24200(18) 0.08611(13) 0.0596(7) Uani 1 1 d U . . H34 H 0.2387 0.2605 0.0718 0.072 Uiso 1 1 calc R . . C35 C 0.0833(2) 0.21252(18) 0.04606(12) 0.0549(7) Uani 1 1 d U . . C36 C -0.0142(2) 0.18437(19) 0.06636(13) 0.0596(7) Uani 1 1 d U . . H36 H -0.0736 0.1638 0.0391 0.072 Uiso 1 1 calc R . . C37 C 0.3552(3) 0.2854(3) 0.1757(2) 0.1103(14) Uani 1 1 d . . . H37A H 0.4052 0.2999 0.2116 0.165 Uiso 1 1 calc R . . H37B H 0.3512 0.3348 0.1478 0.165 Uiso 1 1 calc R . . H37C H 0.3822 0.2337 0.1566 0.165 Uiso 1 1 calc R . . 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 O10 0.129(3) 0.113(2) 0.146(3) -0.019(2) -0.049(2) -0.0025(19) N11 0.081(2) 0.096(2) 0.110(3) 0.007(2) 0.0316(19) -0.0113(19) N21 0.098(2) 0.079(2) 0.0735(18) -0.0017(15) -0.0215(16) 0.0104(15) C10 0.096(3) 0.107(3) 0.096(3) 0.015(2) -0.0054(19) 0.017(2) C11 0.101(3) 0.073(2) 0.137(3) 0.000(2) 0.034(3) -0.015(2) C12 0.071(2) 0.0628(17) 0.157(4) 0.0127(18) 0.012(2) 0.0047(15) C13 0.0517(17) 0.0681(17) 0.126(3) 0.0088(16) 0.0035(16) 0.0010(13) C14 0.074(2) 0.073(2) 0.118(3) 0.0135(17) 0.0038(18) 0.0076(15) C15 0.075(2) 0.109(3) 0.111(3) 0.010(2) 0.0073(19) 0.004(2) C16 0.084(2) 0.071(2) 0.129(3) 0.0146(18) -0.015(2) 0.0043(17) C17 0.081(2) 0.080(2) 0.127(3) 0.018(2) -0.013(2) 0.0037(18) C21 0.103(3) 0.090(3) 0.094(3) -0.0119(19) -0.037(2) -0.016(2) C22 0.101(3) 0.067(2) 0.117(3) 0.0087(17) -0.014(2) -0.0033(17) C23 0.074(2) 0.091(2) 0.080(2) 0.0223(17) -0.0025(15) 0.0013(16) C24 0.096(2) 0.0975(19) 0.0527(19) -0.0079(15) -0.0125(16) -0.0125(18) C25 0.119(3) 0.068(2) 0.067(2) 0.0010(15) -0.0033(19) 0.0047(18) C26 0.086(3) 0.170(4) 0.124(3) 0.044(3) -0.018(2) 0.018(3) C27 0.105(4) 0.211(6) 0.088(3) 0.027(3) -0.001(2) 0.054(3) O31 0.0798(16) 0.133(2) 0.0921(18) 0.0035(15) 0.0285(14) -0.0124(15) O32 0.0955(17) 0.119(2) 0.0550(13) -0.0233(12) -0.0014(12) -0.0205(14) O33 0.0745(14) 0.1127(18) 0.0503(13) 0.0000(11) 0.0080(10) -0.0241(12) C31 0.0608(16) 0.0679(18) 0.0731(17) 0.0021(15) 0.0263(14) 0.0053(13) C32 0.088(2) 0.084(2) 0.0522(17) -0.0104(15) 0.0190(13) 0.0044(16) C33 0.0697(16) 0.0646(17) 0.0554(15) -0.0083(14) 0.0014(13) -0.0026(14) C34 0.0609(15) 0.0576(15) 0.0585(15) 0.0063(13) 0.0001(12) -0.0064(12) C35 0.0613(15) 0.0563(15) 0.0461(15) 0.0038(11) 0.0026(11) 0.0036(12) C36 0.0547(14) 0.0584(16) 0.0646(15) 0.0052(13) 0.0028(13) 0.0029(12) C37 0.078(3) 0.160(4) 0.089(3) -0.002(3) -0.007(2) -0.020(2) _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 O10 C10 1.215(5) . ? N11 C11 1.316(5) . ? N11 C15 1.315(5) . ? N21 C21 1.303(5) . ? N21 C25 1.328(4) . ? C10 C17 1.434(6) . ? C10 C27 1.479(6) . ? C11 C12 1.357(6) . ? C11 H11 0.9300 . ? C12 C13 1.373(5) . ? C12 H12 0.9300 . ? C13 C14 1.385(5) . ? C13 C16 1.437(5) . ? C14 C15 1.371(5) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C17 1.330(5) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C21 C22 1.366(5) . ? C21 H21 0.9300 . ? C22 C23 1.360(5) . ? C22 H22 0.9300 . ? C23 C24 1.362(5) . ? C23 C26 1.482(5) . ? C24 C25 1.376(5) . ? C24 H24 0.9300 . ? C25 H25 0.9300 . ? C26 C27 1.158(6) . ? C26 H26 0.9300 . ? C27 H27 0.9300 . ? O31 C31 1.364(4) . ? O31 H31O 0.8871 . ? O32 C33 1.368(3) . ? O32 C37 1.426(4) . ? O33 C35 1.370(3) . ? O33 H33O 0.7106 . ? C31 C32 1.367(4) . ? C31 C36 1.394(4) . ? C32 C33 1.388(4) . ? C32 H32 0.9300 . ? C33 C34 1.371(4) . ? C34 C35 1.386(4) . ? C34 H34 0.9300 . ? C35 C36 1.380(4) . ? C36 H36 0.9300 . ? C37 H37A 0.9600 . ? C37 H37B 0.9600 . ? C37 H37C 0.9600 . ? 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 C11 N11 C15 118.3(4) . . ? C21 N21 C25 117.2(3) . . ? O10 C10 C17 121.4(4) . . ? O10 C10 C27 123.6(5) . . ? C17 C10 C27 115.0(5) . . ? N11 C11 C12 123.3(4) . . ? N11 C11 H11 118.4 . . ? C12 C11 H11 118.4 . . ? C11 C12 C13 120.0(4) . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C12 C13 C14 116.1(4) . . ? C12 C13 C16 124.7(3) . . ? C14 C13 C16 119.2(3) . . ? C15 C14 C13 120.5(4) . . ? C15 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? N11 C15 C14 121.8(4) . . ? N11 C15 H15 119.1 . . ? C14 C15 H15 119.1 . . ? C17 C16 C13 125.4(4) . . ? C17 C16 H16 117.3 . . ? C13 C16 H16 117.3 . . ? C16 C17 C10 122.6(4) . . ? C16 C17 H17 118.7 . . ? C10 C17 H17 118.7 . . ? N21 C21 C22 123.8(3) . . ? N21 C21 H21 118.1 . . ? C22 C21 H21 118.1 . . ? C23 C22 C21 120.1(3) . . ? C23 C22 H22 120.0 . . ? C21 C22 H22 120.0 . . ? C22 C23 C24 116.3(3) . . ? C22 C23 C26 121.9(4) . . ? C24 C23 C26 121.6(4) . . ? C23 C24 C25 120.7(3) . . ? C23 C24 H24 119.6 . . ? C25 C24 H24 119.6 . . ? N21 C25 C24 121.9(3) . . ? N21 C25 H25 119.1 . . ? C24 C25 H25 119.1 . . ? C27 C26 C23 136.8(6) . . ? C27 C26 H26 111.6 . . ? C23 C26 H26 111.6 . . ? C26 C27 C10 130.1(6) . . ? C26 C27 H27 114.9 . . ? C10 C27 H27 114.9 . . ? C31 O31 H31O 113.4 . . ? C33 O32 C37 118.6(3) . . ? C35 O33 H33O 119.3 . . ? O31 C31 C32 118.4(3) . . ? O31 C31 C36 120.6(3) . . ? C32 C31 C36 120.9(3) . . ? C31 C32 C33 119.4(3) . . ? C31 C32 H32 120.3 . . ? C33 C32 H32 120.3 . . ? C34 C33 O32 125.0(3) . . ? C34 C33 C32 121.1(3) . . ? O32 C33 C32 113.9(3) . . ? C33 C34 C35 118.6(3) . . ? C33 C34 H34 120.7 . . ? C35 C34 H34 120.7 . . ? O33 C35 C36 122.0(3) . . ? O33 C35 C34 116.4(2) . . ? C36 C35 C34 121.6(3) . . ? C35 C36 C31 118.3(3) . . ? C35 C36 H36 120.8 . . ? C31 C36 H36 120.8 . . ? O32 C37 H37A 109.5 . . ? O32 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? O32 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.900 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.900 _refine_diff_density_max 0.325 _refine_diff_density_min -0.303 _refine_diff_density_rms 0.043 # SQUEEZE RESULTS # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 -0.005 0.250 44 5 ' ' 2 0.000 0.005 0.750 44 5 ' ' 3 0.500 0.495 0.250 44 5 ' ' 4 0.500 0.505 0.750 44 5 ' ' _platon_squeeze_details ; ; data_8 _database_code_depnum_ccdc_archive 'CCDC 793080' #TrackingRef '- kb1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,3-bis(4-pyridyl)-2,4-bis(-3(4-pyridyl)propenoyl)cyclobutane ; _chemical_name_common 1,3-bis(4-pyridyl)-2,4-bis(-3(4-pyridyl)propenoyl)cyclobutane _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H24 N4 O2' _chemical_formula_weight 472.53 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 15.178(5) _cell_length_b 6.090(2) _cell_length_c 26.470(8) _cell_angle_alpha 90.00 _cell_angle_beta 102.280(10) _cell_angle_gamma 90.00 _cell_volume 2390.9(13) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3909 _cell_measurement_theta_min 1.43 _cell_measurement_theta_max 25.00 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.313 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 992 _exptl_absorpt_coefficient_mu 0.084 _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 24331 _diffrn_reflns_av_R_equivalents 0.1187 _diffrn_reflns_av_sigmaI/netI 0.0841 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.43 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3909 _reflns_number_gt 1839 _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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3909 _refine_ls_number_parameters 325 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1758 _refine_ls_R_factor_gt 0.0761 _refine_ls_wR_factor_ref 0.2028 _refine_ls_wR_factor_gt 0.1718 _refine_ls_goodness_of_fit_ref 0.966 _refine_ls_restrained_S_all 0.966 _refine_ls_shift/su_max 0.002 _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 C12B C 0.8630(2) 0.7207(7) 0.07305(13) 0.0479(10) Uani 1 1 d . . . H12B H 0.8995 0.5967 0.0785 0.058 Uiso 1 1 calc R . . O1B O 1.02454(19) 1.3709(5) 0.07316(10) 0.0599(8) Uani 1 1 d . . . C13B C 0.8825(2) 0.8899(6) 0.04228(12) 0.0371(9) Uani 1 1 d . . . C17B C 1.0472(2) 1.0218(6) 0.03714(11) 0.0348(9) Uani 1 1 d . . . H17B H 1.1017 0.9314 0.0460 0.042 Uiso 1 1 calc R . . C26B C 1.0843(2) 0.8910(6) 0.14839(13) 0.0442(10) Uani 1 1 d . . . H26B H 1.0936 0.7954 0.1226 0.053 Uiso 1 1 calc R . . C16B C 0.9613(2) 0.8741(6) 0.01632(12) 0.0396(9) Uani 1 1 d . . . H16B H 0.9797 0.7202 0.0151 0.047 Uiso 1 1 calc R . . C23B C 1.1040(2) 0.8072(6) 0.20130(13) 0.0415(10) Uani 1 1 d . . . C1B C 1.0407(2) 1.1767(7) 0.08101(13) 0.0419(10) Uani 1 1 d . . . C14B C 0.8255(3) 1.0684(7) 0.03673(13) 0.0466(10) Uani 1 1 d . . . H14B H 0.8351 1.1876 0.0166 0.056 Uiso 1 1 calc R . . C25B C 1.1656(3) 0.5299(8) 0.26273(18) 0.0628(12) Uani 1 1 d . . . H25B H 1.1922 0.3923 0.2687 0.075 Uiso 1 1 calc R . . C27B C 1.0546(2) 1.0887(7) 0.13367(13) 0.0459(10) Uani 1 1 d . . . H27B H 1.0412 1.1812 0.1590 0.055 Uiso 1 1 calc R . . C15B C 0.7541(3) 1.0683(8) 0.06133(15) 0.0620(13) Uani 1 1 d . . . H15B H 0.7173 1.1918 0.0575 0.074 Uiso 1 1 calc R . . C22B C 1.0846(3) 0.9231(7) 0.24278(14) 0.0549(11) Uani 1 1 d . . . H22B H 1.0560 1.0588 0.2375 0.066 Uiso 1 1 calc R . . N21B N 1.1495(3) 0.6413(7) 0.30291(13) 0.0688(11) Uani 1 1 d . . . C24B C 1.1448(3) 0.6073(7) 0.21227(14) 0.0532(11) Uani 1 1 d . . . H24B H 1.1586 0.5228 0.1857 0.064 Uiso 1 1 calc R . . N11B N 0.7338(2) 0.9045(7) 0.09018(12) 0.0574(10) Uani 1 1 d . . . C21B C 1.1081(3) 0.8358(8) 0.29193(16) 0.0657(13) Uani 1 1 d . . . H21B H 1.0943 0.9164 0.3191 0.079 Uiso 1 1 calc R . . C11B C 0.7902(3) 0.7359(8) 0.09543(14) 0.0562(12) Uani 1 1 d . . . H11B H 0.7793 0.6192 0.1159 0.067 Uiso 1 1 calc R . . O1A O 0.52881(19) 0.1386(5) 0.07404(10) 0.0634(9) Uani 1 1 d . . . C16A C 0.4608(2) 0.6229(6) 0.01685(12) 0.0413(10) Uani 1 1 d . . . H16A H 0.4758 0.7783 0.0141 0.050 Uiso 1 1 calc R . . C13A C 0.3850(2) 0.6019(6) 0.04513(12) 0.0400(9) Uani 1 1 d . . . C17A C 0.5503(2) 0.4872(6) 0.03647(12) 0.0412(10) Uani 1 1 d . . . H17A H 0.6031 0.5839 0.0434 0.049 Uiso 1 1 calc R . . C15A C 0.2951(3) 0.7541(8) 0.10072(14) 0.0578(12) Uani 1 1 d . . . H15A H 0.2841 0.8718 0.1209 0.069 Uiso 1 1 calc R . . N11A N 0.2413(2) 0.5794(7) 0.09717(12) 0.0612(10) Uani 1 1 d . . . C12A C 0.3313(2) 0.4156(7) 0.04233(14) 0.0497(10) Uani 1 1 d . . . H12A H 0.3417 0.2942 0.0231 0.060 Uiso 1 1 calc R . . C1A C 0.5516(2) 0.3304(8) 0.08114(13) 0.0441(10) Uani 1 1 d . . . C26A C 0.5875(3) 0.6175(7) 0.14799(15) 0.0529(11) Uani 1 1 d . . . H26A H 0.5800 0.7236 0.1222 0.063 Uiso 1 1 calc R . . C24A C 0.6598(3) 0.5697(8) 0.24189(15) 0.0686(13) Uani 1 1 d . . . H24A H 0.6845 0.4369 0.2344 0.082 Uiso 1 1 calc R . . C27A C 0.5791(3) 0.4129(8) 0.13461(15) 0.0564(12) Uani 1 1 d . . . H27A H 0.5915 0.3090 0.1609 0.068 Uiso 1 1 calc R . . C14A C 0.3657(3) 0.7696(7) 0.07635(14) 0.0497(11) Uani 1 1 d . . . H14A H 0.4014 0.8952 0.0808 0.060 Uiso 1 1 calc R . . C23A C 0.6086(3) 0.6905(7) 0.20318(14) 0.0513(11) Uani 1 1 d . . . C11A C 0.2614(3) 0.4152(8) 0.06899(14) 0.0556(11) Uani 1 1 d . . . H11A H 0.2261 0.2893 0.0668 0.067 Uiso 1 1 calc R . . C21A C 0.5926(3) 0.9473(8) 0.2678(2) 0.0764(14) Uani 1 1 d . . . H21A H 0.5687 1.0799 0.2760 0.092 Uiso 1 1 calc R . . N21A N 0.6417(3) 0.8318(8) 0.30618(15) 0.0900(15) Uani 1 1 d . . . C25A C 0.6748(4) 0.6448(9) 0.29209(17) 0.0821(16) Uani 1 1 d . . . H25A H 0.7102 0.5594 0.3177 0.098 Uiso 1 1 calc R . . C22A C 0.5749(3) 0.8843(8) 0.21699(16) 0.0626(12) Uani 1 1 d . . . H22A H 0.5400 0.9732 0.1919 0.075 Uiso 1 1 calc R . . 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 C12B 0.040(2) 0.059(3) 0.047(2) 0.010(2) 0.0143(18) -0.001(2) O1B 0.079(2) 0.050(2) 0.0523(17) -0.0013(14) 0.0179(14) 0.0105(16) C13B 0.039(2) 0.041(2) 0.0304(18) -0.0012(17) 0.0064(15) -0.0028(19) C17B 0.0331(19) 0.042(2) 0.0305(18) 0.0060(16) 0.0090(14) 0.0034(17) C26B 0.047(2) 0.052(3) 0.035(2) -0.0009(19) 0.0096(16) 0.003(2) C16B 0.039(2) 0.041(2) 0.040(2) 0.0082(17) 0.0105(15) 0.0088(17) C23B 0.039(2) 0.046(3) 0.039(2) -0.0011(19) 0.0085(16) 0.0021(19) C1B 0.032(2) 0.050(3) 0.046(2) 0.000(2) 0.0130(16) 0.0016(19) C14B 0.058(3) 0.046(3) 0.040(2) 0.0106(19) 0.0194(18) 0.008(2) C25B 0.054(3) 0.064(3) 0.070(3) 0.016(2) 0.011(2) 0.013(2) C27B 0.051(2) 0.057(3) 0.0295(19) -0.0074(19) 0.0077(16) 0.008(2) C15B 0.054(3) 0.080(4) 0.054(2) 0.009(3) 0.016(2) 0.030(3) C22B 0.061(3) 0.060(3) 0.048(2) 0.006(2) 0.0202(19) 0.008(2) N21B 0.087(3) 0.079(3) 0.042(2) 0.014(2) 0.0163(18) 0.010(2) C24B 0.054(3) 0.059(3) 0.047(2) 0.003(2) 0.0099(18) 0.007(2) N11B 0.045(2) 0.085(3) 0.0452(19) 0.006(2) 0.0154(15) -0.001(2) C21B 0.077(3) 0.074(3) 0.049(3) 0.005(2) 0.020(2) 0.010(3) C11B 0.059(3) 0.066(3) 0.046(2) 0.009(2) 0.018(2) -0.005(3) O1A 0.0698(19) 0.054(2) 0.0675(19) 0.0080(16) 0.0170(15) -0.0074(17) C16A 0.045(2) 0.042(3) 0.040(2) 0.0040(18) 0.0131(16) -0.0040(18) C13A 0.038(2) 0.050(3) 0.0324(18) -0.0044(19) 0.0068(15) -0.001(2) C17A 0.033(2) 0.054(3) 0.038(2) -0.0031(18) 0.0115(15) -0.0115(18) C15A 0.055(3) 0.078(4) 0.043(2) -0.022(2) 0.017(2) 0.006(3) N11A 0.051(2) 0.089(3) 0.049(2) -0.016(2) 0.0207(16) -0.002(2) C12A 0.046(2) 0.060(3) 0.050(2) -0.012(2) 0.0248(18) -0.008(2) C1A 0.038(2) 0.061(3) 0.035(2) 0.002(2) 0.0123(16) -0.004(2) C26A 0.058(3) 0.054(3) 0.050(2) 0.010(2) 0.0196(19) -0.002(2) C24A 0.077(3) 0.072(3) 0.055(3) -0.006(2) 0.009(2) 0.004(3) C27A 0.056(3) 0.065(3) 0.050(2) 0.015(2) 0.0148(19) -0.003(2) C14A 0.053(3) 0.048(3) 0.046(2) -0.009(2) 0.0044(19) -0.001(2) C23A 0.049(2) 0.061(3) 0.046(2) 0.004(2) 0.0136(19) 0.002(2) C11A 0.052(3) 0.066(3) 0.053(2) -0.009(2) 0.022(2) -0.016(2) C21A 0.089(4) 0.054(3) 0.093(4) -0.017(3) 0.034(3) -0.001(3) N21A 0.130(4) 0.086(4) 0.057(3) -0.019(3) 0.028(3) -0.016(3) C25A 0.107(4) 0.089(4) 0.048(3) 0.011(3) 0.012(3) -0.005(3) C22A 0.066(3) 0.064(3) 0.058(3) 0.003(2) 0.014(2) 0.006(2) _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 C12B C11B 1.363(5) . ? C12B C13B 1.384(5) . ? O1B C1B 1.217(4) . ? C13B C14B 1.377(5) . ? C13B C16B 1.504(5) . ? C17B C1B 1.516(5) . ? C17B C16B 1.531(4) 3_775 ? C17B C16B 1.583(5) . ? C26B C27B 1.315(5) . ? C26B C23B 1.461(5) . ? C16B C17B 1.531(4) 3_775 ? C23B C24B 1.368(5) . ? C23B C22B 1.389(5) . ? C1B C27B 1.466(5) . ? C14B C15B 1.378(5) . ? C25B N21B 1.327(5) . ? C25B C24B 1.388(5) . ? C15B N11B 1.331(5) . ? C22B C21B 1.380(5) . ? N21B C21B 1.344(5) . ? N11B C11B 1.325(5) . ? O1A C1A 1.221(4) . ? C16A C13A 1.506(5) . ? C16A C17A 1.539(4) 3_665 ? C16A C17A 1.579(5) . ? C13A C14A 1.384(5) . ? C13A C12A 1.391(5) . ? C17A C1A 1.516(5) . ? C17A C16A 1.539(4) 3_665 ? C15A N11A 1.332(5) . ? C15A C14A 1.366(5) . ? N11A C11A 1.322(5) . ? C12A C11A 1.393(5) . ? C1A C27A 1.476(5) . ? C26A C27A 1.294(5) . ? C26A C23A 1.495(5) . ? C24A C25A 1.378(6) . ? C24A C23A 1.362(5) . ? C23A C22A 1.367(5) . ? C21A C22A 1.370(6) . ? C21A N21A 1.326(6) . ? N21A C25A 1.330(6) . ? 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 C11B C12B C13B 120.0(4) . . ? C14B C13B C12B 116.3(3) . . ? C14B C13B C16B 123.0(3) . . ? C12B C13B C16B 120.8(3) . . ? C1B C17B C16B 116.3(3) . 3_775 ? C1B C17B C16B 116.0(3) . . ? C16B C17B C16B 90.7(2) 3_775 . ? C27B C26B C23B 126.3(4) . . ? C13B C16B C17B 118.5(3) . 3_775 ? C13B C16B C17B 118.7(3) . . ? C17B C16B C17B 89.3(2) 3_775 . ? C24B C23B C22B 116.5(4) . . ? C24B C23B C26B 120.4(4) . . ? C22B C23B C26B 123.1(4) . . ? O1B C1B C27B 120.0(4) . . ? O1B C1B C17B 121.2(3) . . ? C27B C1B C17B 118.8(4) . . ? C15B C14B C13B 119.2(4) . . ? N21B C25B C24B 123.7(4) . . ? C26B C27B C1B 126.0(4) . . ? N11B C15B C14B 124.9(4) . . ? C21B C22B C23B 119.6(4) . . ? C21B N21B C25B 115.8(4) . . ? C25B C24B C23B 120.4(4) . . ? C11B N11B C15B 114.7(3) . . ? N21B C21B C22B 123.9(4) . . ? N11B C11B C12B 124.9(4) . . ? C13A C16A C17A 118.2(3) . 3_665 ? C13A C16A C17A 119.1(3) . . ? C17A C16A C17A 89.6(3) 3_665 . ? C14A C13A C12A 115.9(3) . . ? C14A C13A C16A 121.1(3) . . ? C12A C13A C16A 123.0(3) . . ? C1A C17A C16A 114.9(3) . 3_665 ? C1A C17A C16A 117.0(3) . . ? C16A C17A C16A 90.4(3) 3_665 . ? N11A C15A C14A 123.5(4) . . ? C15A N11A C11A 115.6(3) . . ? C11A C12A C13A 118.4(4) . . ? O1A C1A C27A 119.1(4) . . ? O1A C1A C17A 121.7(3) . . ? C27A C1A C17A 119.2(4) . . ? C27A C26A C23A 122.8(4) . . ? C25A C24A C23A 119.8(5) . . ? C26A C27A C1A 125.5(4) . . ? C13A C14A C15A 121.2(4) . . ? C22A C23A C24A 116.8(4) . . ? C22A C23A C26A 120.2(4) . . ? C24A C23A C26A 123.0(4) . . ? N11A C11A C12A 125.2(4) . . ? C22A C21A N21A 124.4(5) . . ? C25A N21A C21A 115.1(4) . . ? N21A C25A C24A 124.1(5) . . ? C21A C22A C23A 119.9(4) . . ? _diffrn_measured_fraction_theta_max 0.927 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.927 _refine_diff_density_max 0.220 _refine_diff_density_min -0.200 _refine_diff_density_rms 0.050