# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_requested_category ? _publ_contact_author_name 'Reijo Sillanpaa' _publ_contact_author_email resillan@jyu.fi loop_ _publ_author_name A.Riisio M.M.Hanninen R.Sillanpa data_H4L1_1 _database_code_depnum_ccdc_archive 'CCDC 888651' #TrackingRef '- New_All_cifs.cif' _audit_creation_date 2012-06-04T16:28:31-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C42 H56 N2 O4' _chemical_formula_sum 'C42 H56 N2 O4' _chemical_formula_weight 652.89 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 10.3558(5) _cell_length_b 26.5600(14) _cell_length_c 14.0029(7) _cell_angle_alpha 90 _cell_angle_beta 107.368(3) _cell_angle_gamma 90 _cell_volume 3675.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 2507 _cell_measurement_theta_min 3.3331 _cell_measurement_theta_max 74.6594 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.18 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1416 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.585 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.712 _exptl_absorpt_correction_T_max 1 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 10.3953 _diffrn_orient_matrix_ub_11 -0.1113331 _diffrn_orient_matrix_ub_12 0.0350717 _diffrn_orient_matrix_ub_13 0.0145752 _diffrn_orient_matrix_ub_21 0.0546181 _diffrn_orient_matrix_ub_22 0.0432318 _diffrn_orient_matrix_ub_23 -0.0507718 _diffrn_orient_matrix_ub_31 -0.094304 _diffrn_orient_matrix_ub_32 -0.0165179 _diffrn_orient_matrix_ub_33 -0.1029726 _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_reflns_av_R_equivalents 0.024 _diffrn_reflns_av_unetI/netI 0.0313 _diffrn_reflns_number 7109 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.33 _diffrn_reflns_theta_max 69.99 _diffrn_reflns_theta_full 69.99 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _reflns_number_total 3468 _reflns_number_gt 2761 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0619P)^2^+3.1657P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3468 _refine_ls_number_parameters 243 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0658 _refine_ls_R_factor_gt 0.0523 _refine_ls_wR_factor_ref 0.1454 _refine_ls_wR_factor_gt 0.1347 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.40560(16) 0.06393(5) 0.58122(10) 0.0417(4) Uani 1 1 d D . . H1 H 0.415(2) 0.0782(9) 0.5240(14) 0.050 Uiso 1 1 d D . . O2 O 0.56764(14) 0.03975(5) 0.42940(11) 0.0415(4) Uani 1 1 d D . . H2 H 0.598(2) 0.0072(7) 0.4338(18) 0.050 Uiso 1 1 d D . . N8 N 0.39778(15) 0.13123(6) 0.43933(11) 0.0322(4) Uani 1 1 d . . . C1 C 0.36160(19) 0.10182(7) 0.63106(13) 0.0336(4) Uani 1 1 d . A . C2 C 0.3060(2) 0.08907(8) 0.70824(14) 0.0405(5) Uani 1 1 d . . . C3 C 0.2623(2) 0.12808(9) 0.75773(14) 0.0423(5) Uani 1 1 d . . . H3 H 0.2240 0.1199 0.8095 0.051 Uiso 1 1 calc R . . C4 C 0.2729(2) 0.17840(9) 0.73405(14) 0.0441(5) Uani 1 1 d . . . C5 C 0.3288(2) 0.18980(8) 0.65750(14) 0.0406(5) Uani 1 1 d . A . H5 H 0.3366 0.2240 0.6403 0.049 Uiso 1 1 calc R . . C6 C 0.37351(18) 0.15211(7) 0.60572(13) 0.0325(4) Uani 1 1 d . . . C7 C 0.4400(2) 0.16549(7) 0.52573(14) 0.0349(4) Uani 1 1 d . A . H7A H 0.4157 0.2005 0.5029 0.042 Uiso 1 1 calc R . . H7B H 0.5396 0.1638 0.5549 0.042 Uiso 1 1 calc R . . C9 C 0.48286(18) 0.13680(8) 0.37160(13) 0.0339(4) Uani 1 1 d . A . H9A H 0.4759 0.1719 0.3466 0.041 Uiso 1 1 calc R . . H9B H 0.4476 0.1143 0.3132 0.041 Uiso 1 1 calc R . . C10 C 0.62895(18) 0.12455(7) 0.42145(13) 0.0313(4) Uani 1 1 d . . . C11 C 0.72711(19) 0.16207(8) 0.44043(14) 0.0353(4) Uani 1 1 d . A . H11 H 0.7004 0.1956 0.4207 0.042 Uiso 1 1 calc R . . C12 C 0.86299(19) 0.15198(8) 0.48737(15) 0.0391(5) Uani 1 1 d . . . C13 C 0.89887(19) 0.10274(8) 0.51688(14) 0.0386(5) Uani 1 1 d . A . H13 H 0.9912 0.0953 0.5500 0.046 Uiso 1 1 calc R . . C14 C 0.8044(2) 0.06372(8) 0.49972(14) 0.0367(4) Uani 1 1 d . . . C15 C 0.66944(19) 0.07503(7) 0.45029(13) 0.0329(4) Uani 1 1 d . A . C19 C 0.2240(3) 0.22005(11) 0.78894(18) 0.0643(8) Uani 1 1 d . . . H19A H 0.2244 0.2080 0.8552 0.096 Uiso 1 1 calc R . . H19B H 0.1318 0.2298 0.7506 0.096 Uiso 1 1 calc R . . H19C H 0.2841 0.2492 0.7965 0.096 Uiso 1 1 calc R . . C20 C 0.2970(3) 0.03498(9) 0.73838(18) 0.0591(7) Uani 1 1 d . . . H20A H 0.2262 0.0177 0.6864 0.089 Uiso 1 1 calc R . . H20B H 0.2750 0.0338 0.8017 0.089 Uiso 1 1 calc R . . H20C H 0.3840 0.0182 0.7466 0.089 Uiso 1 1 calc R . . C21 C 0.8470(2) 0.01117(9) 0.53690(18) 0.0509(6) Uani 1 1 d . A . H21A H 0.7838 -0.0022 0.5706 0.076 Uiso 1 1 calc R . . H21B H 0.9384 0.0121 0.5841 0.076 Uiso 1 1 calc R . . H21C H 0.8464 -0.0105 0.4801 0.076 Uiso 1 1 calc R . . C22 C 0.9671(2) 0.19339(10) 0.5065(2) 0.0550(6) Uani 1 1 d . A . H22A H 0.9818 0.2034 0.4432 0.083 Uiso 1 1 calc R . . H22B H 1.0523 0.1813 0.5527 0.083 Uiso 1 1 calc R . . H22C H 0.9348 0.2224 0.5361 0.083 Uiso 1 1 calc R . . C16A C 0.2506(4) 0.13076(19) 0.3812(3) 0.0330(10) Uiso 0.50 1 d P A 1 H16A H 0.1977 0.1281 0.4294 0.040 Uiso 0.50 1 calc PR A 1 H16B H 0.2281 0.1636 0.3467 0.040 Uiso 0.50 1 calc PR A 1 C17A C 0.2044(8) 0.0901(2) 0.3052(6) 0.0420(15) Uani 0.50 1 d P A 1 H17A H 0.2541 0.0586 0.3307 0.050 Uiso 0.50 1 calc PR A 1 H17B H 0.2252 0.0997 0.2431 0.050 Uiso 0.50 1 calc PR A 1 C18A C 0.0506(4) 0.08059(18) 0.2812(3) 0.0425(9) Uani 0.50 1 d P . 1 H18A H 0.0274 0.0487 0.2433 0.051 Uiso 0.50 1 calc PR . 1 H18B H 0.0281 0.0766 0.3447 0.051 Uiso 0.50 1 calc PR . 1 C16B C 0.2592(4) 0.14854(18) 0.3868(3) 0.0269(9) Uiso 0.50 1 d P A 2 H16C H 0.2635 0.1811 0.3536 0.032 Uiso 0.50 1 calc PR A 2 H16D H 0.2089 0.1538 0.4361 0.032 Uiso 0.50 1 calc PR A 2 C17B C 0.1848(7) 0.1104(2) 0.3094(5) 0.0360(13) Uani 0.50 1 d P A 2 H17C H 0.2014 0.0760 0.3378 0.043 Uiso 0.50 1 calc PR A 2 H17D H 0.2185 0.1120 0.2503 0.043 Uiso 0.50 1 calc PR A 2 C18B C 0.0325(4) 0.1219(2) 0.2779(3) 0.0431(10) Uani 0.50 1 d P . 2 H18C H 0.0043 0.1279 0.3386 0.052 Uiso 0.50 1 calc PR . 2 H18D H 0.0152 0.1532 0.2376 0.052 Uiso 0.50 1 calc PR . 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0627(9) 0.0335(7) 0.0389(7) -0.0010(6) 0.0304(7) -0.0006(7) O2 0.0410(8) 0.0340(7) 0.0559(9) -0.0032(6) 0.0243(7) -0.0043(6) N8 0.0276(7) 0.0480(9) 0.0239(7) 0.0020(6) 0.0122(6) 0.0017(7) C1 0.0366(10) 0.0406(10) 0.0272(8) -0.0023(7) 0.0149(7) 0.0005(8) C2 0.0450(11) 0.0495(12) 0.0311(9) 0.0022(8) 0.0177(8) -0.0033(9) C3 0.0408(11) 0.0651(14) 0.0258(9) 0.0021(9) 0.0175(8) 0.0044(10) C4 0.0472(12) 0.0590(14) 0.0291(9) -0.0005(9) 0.0159(8) 0.0156(10) C5 0.0498(12) 0.0424(11) 0.0329(10) 0.0018(8) 0.0176(9) 0.0111(9) C6 0.0330(9) 0.0404(10) 0.0267(9) 0.0008(7) 0.0128(7) 0.0039(8) C7 0.0429(10) 0.0344(10) 0.0331(9) 0.0010(8) 0.0199(8) 0.0010(8) C9 0.0349(10) 0.0433(11) 0.0281(9) 0.0035(8) 0.0164(7) -0.0001(8) C10 0.0321(9) 0.0406(10) 0.0262(8) -0.0017(7) 0.0162(7) -0.0015(8) C11 0.0382(10) 0.0369(10) 0.0382(10) -0.0006(8) 0.0228(8) -0.0029(8) C12 0.0356(10) 0.0487(12) 0.0392(10) -0.0079(9) 0.0205(8) -0.0072(9) C13 0.0319(9) 0.0529(12) 0.0351(10) -0.0034(9) 0.0159(8) 0.0015(9) C14 0.0387(10) 0.0439(11) 0.0347(9) -0.0006(8) 0.0217(8) 0.0043(8) C15 0.0355(9) 0.0370(10) 0.0332(9) -0.0042(7) 0.0210(8) -0.0036(8) C19 0.0853(19) 0.0745(18) 0.0430(12) 0.0025(12) 0.0345(13) 0.0323(15) C20 0.0896(19) 0.0541(14) 0.0466(13) 0.0041(11) 0.0403(13) -0.0114(13) C21 0.0503(13) 0.0525(13) 0.0573(13) 0.0073(11) 0.0271(11) 0.0121(11) C22 0.0432(12) 0.0602(15) 0.0677(15) -0.0127(12) 0.0258(11) -0.0150(11) C17A 0.033(3) 0.056(4) 0.038(2) -0.012(3) 0.012(2) 0.000(3) C18A 0.036(2) 0.051(3) 0.037(2) -0.0105(18) 0.0070(15) -0.0018(19) C17B 0.034(3) 0.048(4) 0.026(2) 0.004(3) 0.0089(19) 0.003(3) C18B 0.034(3) 0.066(3) 0.030(2) 0.0060(17) 0.0106(16) 0.0051(19) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.377(2) . ? O1 H1 0.917(16) . ? O2 C15 1.375(2) . ? O2 H2 0.914(16) . ? N8 C7 1.472(2) . ? N8 C16B 1.477(4) . ? N8 C9 1.482(2) . ? N8 C16A 1.499(4) . ? C1 C6 1.397(3) . ? C1 C2 1.409(3) . ? C2 C3 1.395(3) . ? C2 C20 1.508(3) . ? C3 C4 1.389(3) . ? C3 H3 0.9500 . ? C4 C5 1.395(3) . ? C4 C19 1.518(3) . ? C5 C6 1.394(3) . ? C5 H5 0.9500 . ? C6 C7 1.522(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C9 C10 1.500(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.391(3) . ? C10 C15 1.403(3) . ? C11 C12 1.390(3) . ? C11 H11 0.9500 . ? C12 C13 1.388(3) . ? C12 C22 1.507(3) . ? C13 C14 1.396(3) . ? C13 H13 0.9500 . ? C14 C15 1.395(3) . ? C14 C21 1.509(3) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C16A C17A 1.492(8) . ? C16A H16A 0.9900 . ? C16A H16B 0.9900 . ? C17A C18A 1.547(9) . ? C17A H17A 0.9900 . ? C17A H17B 0.9900 . ? C18A C18B 1.485(6) 2 ? C18A H18A 0.9900 . ? C18A H18B 0.9900 . ? C16B C17B 1.515(8) . ? C16B H16C 0.9900 . ? C16B H16D 0.9900 . ? C17B C18B 1.537(8) . ? C17B H17C 0.9900 . ? C17B H17D 0.9900 . ? C18B C18A 1.485(6) 2 ? C18B H18C 0.9900 . ? C18B H18D 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 H1 106.1(16) . . ? C15 O2 H2 114.0(15) . . ? C7 N8 C16B 102.9(2) . . ? C7 N8 C9 112.13(15) . . ? C16B N8 C9 108.99(19) . . ? C7 N8 C16A 117.1(2) . . ? C16B N8 C16A 18.66(19) . . ? C9 N8 C16A 110.9(2) . . ? O1 C1 C6 120.14(16) . . ? O1 C1 C2 119.06(18) . . ? C6 C1 C2 120.79(18) . . ? C3 C2 C1 118.03(19) . . ? C3 C2 C20 120.81(18) . . ? C1 C2 C20 121.14(19) . . ? C4 C3 C2 122.39(18) . . ? C4 C3 H3 118.8 . . ? C2 C3 H3 118.8 . . ? C3 C4 C5 118.19(19) . . ? C3 C4 C19 121.23(19) . . ? C5 C4 C19 120.6(2) . . ? C6 C5 C4 121.5(2) . . ? C6 C5 H5 119.3 . . ? C4 C5 H5 119.3 . . ? C5 C6 C1 119.10(17) . . ? C5 C6 C7 120.59(18) . . ? C1 C6 C7 120.26(16) . . ? N8 C7 C6 111.83(15) . . ? N8 C7 H7A 109.2 . . ? C6 C7 H7A 109.2 . . ? N8 C7 H7B 109.2 . . ? C6 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? N8 C9 C10 112.97(14) . . ? N8 C9 H9A 109.0 . . ? C10 C9 H9A 109.0 . . ? N8 C9 H9B 109.0 . . ? C10 C9 H9B 109.0 . . ? H9A C9 H9B 107.8 . . ? C11 C10 C15 118.56(17) . . ? C11 C10 C9 120.76(18) . . ? C15 C10 C9 120.68(17) . . ? C12 C11 C10 122.08(19) . . ? C12 C11 H11 119.0 . . ? C10 C11 H11 119.0 . . ? C13 C12 C11 117.76(18) . . ? C13 C12 C22 121.4(2) . . ? C11 C12 C22 120.9(2) . . ? C12 C13 C14 122.45(18) . . ? C12 C13 H13 118.8 . . ? C14 C13 H13 118.8 . . ? C15 C14 C13 118.20(19) . . ? C15 C14 C21 121.12(19) . . ? C13 C14 C21 120.65(19) . . ? O2 C15 C14 123.36(18) . . ? O2 C15 C10 115.69(16) . . ? C14 C15 C10 120.92(18) . . ? C4 C19 H19A 109.5 . . ? C4 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C4 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C2 C20 H20A 109.5 . . ? C2 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C2 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C14 C21 H21A 109.5 . . ? C14 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C14 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C12 C22 H22A 109.5 . . ? C12 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C12 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C17A C16A N8 116.8(4) . . ? C17A C16A H16A 108.1 . . ? N8 C16A H16A 108.1 . . ? C17A C16A H16B 108.1 . . ? N8 C16A H16B 108.1 . . ? H16A C16A H16B 107.3 . . ? C16A C17A C18A 111.3(5) . . ? C16A C17A H17A 109.4 . . ? C18A C17A H17A 109.4 . . ? C16A C17A H17B 109.4 . . ? C18A C17A H17B 109.4 . . ? H17A C17A H17B 108.0 . . ? C18B C18A C17A 112.9(4) 2 . ? C18B C18A H18A 109.0 2 . ? C17A C18A H18A 109.0 . . ? C18B C18A H18B 109.0 2 . ? C17A C18A H18B 109.0 . . ? H18A C18A H18B 107.8 . . ? N8 C16B C17B 111.0(4) . . ? N8 C16B H16C 109.4 . . ? C17B C16B H16C 109.4 . . ? N8 C16B H16D 109.4 . . ? C17B C16B H16D 109.4 . . ? H16C C16B H16D 108.0 . . ? C16B C17B C18B 109.4(4) . . ? C16B C17B H17C 109.8 . . ? C18B C17B H17C 109.8 . . ? C16B C17B H17D 109.8 . . ? C18B C17B H17D 109.8 . . ? H17C C17B H17D 108.2 . . ? C18A C18B C17B 112.8(4) 2 . ? C18A C18B H18C 109.0 2 . ? C17B C18B H18C 109.0 . . ? C18A C18B H18D 109.0 2 . ? C17B C18B H18D 109.0 . . ? H18C C18B H18D 107.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 179.91(18) . . . . ? C6 C1 C2 C3 0.6(3) . . . . ? O1 C1 C2 C20 1.4(3) . . . . ? C6 C1 C2 C20 -178.0(2) . . . . ? C1 C2 C3 C4 -0.5(3) . . . . ? C20 C2 C3 C4 178.0(2) . . . . ? C2 C3 C4 C5 0.3(3) . . . . ? C2 C3 C4 C19 179.8(2) . . . . ? C3 C4 C5 C6 -0.1(3) . . . . ? C19 C4 C5 C6 -179.6(2) . . . . ? C4 C5 C6 C1 0.2(3) . . . . ? C4 C5 C6 C7 -177.21(19) . . . . ? O1 C1 C6 C5 -179.72(17) . . . . ? C2 C1 C6 C5 -0.4(3) . . . . ? O1 C1 C6 C7 -2.3(3) . . . . ? C2 C1 C6 C7 176.98(18) . . . . ? C16B N8 C7 C6 75.3(2) . . . . ? C9 N8 C7 C6 -167.75(15) . . . . ? C16A N8 C7 C6 62.4(3) . . . . ? C5 C6 C7 N8 -140.76(18) . . . . ? C1 C6 C7 N8 41.9(2) . . . . ? C7 N8 C9 C10 61.5(2) . . . . ? C16B N8 C9 C10 174.8(2) . . . . ? C16A N8 C9 C10 -165.5(2) . . . . ? N8 C9 C10 C11 -111.48(19) . . . . ? N8 C9 C10 C15 68.3(2) . . . . ? C15 C10 C11 C12 -0.4(3) . . . . ? C9 C10 C11 C12 179.34(16) . . . . ? C10 C11 C12 C13 -1.0(3) . . . . ? C10 C11 C12 C22 179.74(18) . . . . ? C11 C12 C13 C14 1.0(3) . . . . ? C22 C12 C13 C14 -179.81(18) . . . . ? C12 C13 C14 C15 0.5(3) . . . . ? C12 C13 C14 C21 -177.44(18) . . . . ? C13 C14 C15 O2 -179.92(16) . . . . ? C21 C14 C15 O2 -2.0(3) . . . . ? C13 C14 C15 C10 -2.0(3) . . . . ? C21 C14 C15 C10 175.94(17) . . . . ? C11 C10 C15 O2 -179.98(15) . . . . ? C9 C10 C15 O2 0.3(2) . . . . ? C11 C10 C15 C14 2.0(3) . . . . ? C9 C10 C15 C14 -177.79(16) . . . . ? C7 N8 C16A C17A -169.8(4) . . . . ? C16B N8 C16A C17A 147.4(11) . . . . ? C9 N8 C16A C17A 59.8(5) . . . . ? N8 C16A C17A C18A 157.8(4) . . . . ? C16A C17A C18A C18B 71.7(6) . . . 2 ? C7 N8 C16B C17B -166.3(4) . . . . ? C9 N8 C16B C17B 74.5(4) . . . . ? C16A N8 C16B C17B -24.6(7) . . . . ? N8 C16B C17B C18B 164.3(4) . . . . ? C16B C17B C18B C18A -168.0(4) . . . 2 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 N8 0.917(16) 1.816(19) 2.656(2) 151(2) . O2 H2 O1 0.914(16) 1.900(18) 2.776(2) 160(2) 5_656 _refine_diff_density_max 0.318 _refine_diff_density_min -0.179 _refine_diff_density_rms 0.042 # END of CIF data_H4L2_2 _database_code_depnum_ccdc_archive 'CCDC 888652' #TrackingRef '- New_All_cifs.cif' _audit_creation_date 2012-06-05T10:43:17-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C44 H60 N2 O4' _chemical_formula_sum 'C44 H60 N2 O4' _chemical_formula_weight 680.94 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M 'P 41 21 2' _symmetry_space_group_name_Hall 'P 4abw 2nw' _symmetry_Int_Tables_number 92 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y+1/2, x+1/2, z+1/4' 'y+1/2, -x+1/2, z+3/4' '-x+1/2, y+1/2, -z+1/4' 'x+1/2, -y+1/2, -z+3/4' 'y, x, -z' '-y, -x, -z+1/2' _cell_length_a 10.2750(3) _cell_length_b 10.2750(3) _cell_length_c 37.3096(10) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 3938.98(19) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 17484 _cell_measurement_theta_min 0.407 _cell_measurement_theta_max 27.103 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.148 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1480 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0277 _diffrn_reflns_av_unetI/netI 0.0366 _diffrn_reflns_number 6908 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -46 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_theta_min 2.8 _diffrn_reflns_theta_max 25.99 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _reflns_number_total 3835 _reflns_number_gt 3175 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0690P)^2^+2.5715P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 3835 _refine_ls_number_parameters 234 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0827 _refine_ls_R_factor_gt 0.0671 _refine_ls_wR_factor_ref 0.1706 _refine_ls_wR_factor_gt 0.1589 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.083 _refine_ls_shift/su_max 0.015 _refine_ls_shift/su_mean 0.001 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(2) _refine_diff_density_max 0.451 _refine_diff_density_min -0.376 _refine_diff_density_rms 0.043 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.2948(2) 0.5967(2) 0.03240(7) 0.0504(6) Uani 1 1 d . . . H1 H 0.275(4) 0.585(4) 0.0091(11) 0.076 Uiso 1 1 d . . . O2 O 0.4179(2) 0.4967(2) -0.04173(7) 0.0569(7) Uani 1 1 d . . . H2 H 0.496(5) 0.456(4) -0.0415(12) 0.085 Uiso 1 1 d . . . N8 N 0.1436(2) 0.6033(2) -0.02626(6) 0.0367(6) Uani 1 1 d . B . C1 C 0.2075(3) 0.6810(3) 0.04780(8) 0.0394(7) Uani 1 1 d . . . C2 C 0.2082(3) 0.6986(3) 0.08487(8) 0.0434(7) Uani 1 1 d . . . C3 C 0.1221(3) 0.7867(3) 0.09977(8) 0.0455(8) Uani 1 1 d . . . H3 H 0.1246 0.8011 0.1249 0.055 Uiso 1 1 calc R . . C4 C 0.0321(3) 0.8551(3) 0.07933(7) 0.0402(7) Uani 1 1 d . . . C5 C 0.0318(3) 0.8332(3) 0.04245(8) 0.0381(7) Uani 1 1 d . . . H5 H -0.0302 0.8774 0.028 0.046 Uiso 1 1 calc R . . C6 C 0.1192(3) 0.7492(3) 0.02613(7) 0.0370(7) Uani 1 1 d . . . C7 C 0.1260(3) 0.7381(3) -0.01383(8) 0.0419(7) Uani 1 1 d . . . H7A H 0.0449 0.7735 -0.0243 0.05 Uiso 1 1 calc R . . H7B H 0.1994 0.7917 -0.0227 0.05 Uiso 1 1 calc R . . C9 C 0.1854(3) 0.6016(3) -0.06401(8) 0.0396(7) Uani 1 1 d . . . H9A H 0.1175 0.6436 -0.0789 0.048 Uiso 1 1 calc R . . H9B H 0.1938 0.5102 -0.072 0.048 Uiso 1 1 calc R . . C10 C 0.3126(3) 0.6703(3) -0.06995(8) 0.0388(7) Uani 1 1 d . . . C11 C 0.3168(3) 0.7899(3) -0.08701(8) 0.0422(7) Uani 1 1 d . . . H11 H 0.238 0.8265 -0.0957 0.051 Uiso 1 1 calc R . . C12 C 0.4324(3) 0.8584(3) -0.09187(9) 0.0466(8) Uani 1 1 d . . . C13 C 0.5457(3) 0.8018(3) -0.07917(9) 0.0478(8) Uani 1 1 d . . . H13 H 0.6254 0.8474 -0.082 0.057 Uiso 1 1 calc R . . C14 C 0.5475(3) 0.6805(3) -0.06234(8) 0.0450(8) Uani 1 1 d . . . C15 C 0.4291(3) 0.6156(3) -0.05782(8) 0.0415(7) Uani 1 1 d . . . C16 C 0.0200(3) 0.5312(3) -0.02157(9) 0.0479(8) Uani 1 1 d . . . H16A H -0.0504 0.5808 -0.0335 0.057 Uiso 1 1 calc R A 1 H16B H -0.0006 0.5278 0.0043 0.057 Uiso 1 1 calc R A 1 C17A C 0.0192(8) 0.3955(8) -0.0359(2) 0.060(2) Uiso 0.5 1 d P B 1 H17A H 0.0307 0.3987 -0.0623 0.072 Uiso 0.5 1 calc PR B 1 H17B H -0.0666 0.3556 -0.031 0.072 Uiso 0.5 1 calc PR B 1 C18A C 0.1250(10) 0.3100(10) -0.0199(3) 0.085(3) Uiso 0.5 1 d P B 1 H18A H 0.2066 0.3504 -0.0285 0.102 Uiso 0.5 1 calc PR B 1 H18B H 0.1212 0.3303 0.006 0.102 Uiso 0.5 1 calc PR B 1 C19A C 0.1541(19) 0.1687(17) -0.02071(15) 0.151(6) Uiso 0.5 1 d PD B 1 H19A H 0.2355 0.1485 -0.0338 0.181 Uiso 0.5 1 calc PR B 1 H19B H 0.0812 0.1165 -0.0305 0.181 Uiso 0.5 1 calc PR B 1 C17B C 0.0375(7) 0.3800(7) -0.02086(18) 0.0480(17) Uiso 0.5 1 d PD B 2 H17C H -0.0499 0.3397 -0.022 0.058 Uiso 0.5 1 calc PR B 2 H17D H 0.0848 0.3541 -0.0428 0.058 Uiso 0.5 1 calc PR B 2 C18B C 0.1102(6) 0.3217(6) 0.01173(15) 0.0441(14) Uiso 0.5 1 d PD B 2 H18C H 0.2029 0.3474 0.0103 0.053 Uiso 0.5 1 calc PR B 2 H18D H 0.0738 0.36 0.0339 0.053 Uiso 0.5 1 calc PR B 2 C19B C 0.1028(11) 0.1812(8) 0.0144(3) 0.076(2) Uiso 0.5 1 d PD B 2 H19C H 0.0102 0.1553 0.0127 0.091 Uiso 0.5 1 calc PR B 2 H19D H 0.1344 0.1552 0.0384 0.091 Uiso 0.5 1 calc PR B 2 C20 C -0.0614(4) 0.9508(4) 0.09558(9) 0.0536(9) Uani 1 1 d . . . H20A H -0.0429 0.9601 0.1212 0.08 Uiso 1 1 calc R . . H20B H -0.1507 0.9193 0.0924 0.08 Uiso 1 1 calc R . . H20C H -0.0517 1.0354 0.0837 0.08 Uiso 1 1 calc R . . C21 C 0.3016(4) 0.6215(4) 0.10773(9) 0.0596(10) Uani 1 1 d . . . H21A H 0.2988 0.5297 0.1006 0.089 Uiso 1 1 calc R . . H21B H 0.2766 0.6293 0.133 0.089 Uiso 1 1 calc R . . H21C H 0.39 0.6552 0.1045 0.089 Uiso 1 1 calc R . . C22 C 0.4333(4) 0.9895(4) -0.10989(11) 0.0630(10) Uani 1 1 d . . . H22A H 0.3697 0.9901 -0.1295 0.094 Uiso 1 1 calc R . . H22B H 0.5203 1.0069 -0.1196 0.094 Uiso 1 1 calc R . . H22C H 0.4106 1.0569 -0.0924 0.094 Uiso 1 1 calc R . . C23 C 0.6754(3) 0.6239(4) -0.04985(11) 0.0616(10) Uani 1 1 d . . . H23A H 0.6603 0.5678 -0.029 0.092 Uiso 1 1 calc R . . H23B H 0.7347 0.6946 -0.0432 0.092 Uiso 1 1 calc R . . H23C H 0.7141 0.5725 -0.0692 0.092 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 O1 0.0399(13) 0.0498(14) 0.0616(13) -0.0022(12) -0.0133(11) 0.0147(11) O2 0.0407(14) 0.0473(14) 0.0828(17) 0.0168(12) 0.0052(12) 0.0154(11) N8 0.0288(12) 0.0340(13) 0.0474(14) -0.0006(11) 0.0007(10) 0.0014(10) C1 0.0320(16) 0.0331(16) 0.0532(16) -0.0006(14) -0.0067(13) -0.0007(13) C2 0.0405(17) 0.0392(17) 0.0506(17) 0.0103(14) -0.0124(14) -0.0028(15) C3 0.054(2) 0.0417(18) 0.0412(15) 0.0060(13) -0.0070(15) -0.0067(16) C4 0.0428(17) 0.0370(17) 0.0409(15) 0.0021(12) 0.0003(13) -0.0038(14) C5 0.0383(17) 0.0348(16) 0.0411(15) 0.0054(12) -0.0019(13) 0.0045(13) C6 0.0345(16) 0.0330(15) 0.0435(15) 0.0052(13) -0.0012(13) 0.0005(13) C7 0.0451(18) 0.0347(16) 0.0459(16) 0.0009(13) 0.0007(14) 0.0102(14) C9 0.0332(15) 0.0366(16) 0.0490(17) -0.0071(13) -0.0037(13) 0.0035(13) C10 0.0332(16) 0.0400(17) 0.0434(15) -0.0040(13) 0.0032(13) 0.0035(13) C11 0.0320(16) 0.0468(19) 0.0476(16) -0.0020(14) -0.0018(14) 0.0071(14) C12 0.0399(18) 0.0439(19) 0.0560(19) -0.0039(15) 0.0019(14) 0.0023(15) C13 0.0335(17) 0.048(2) 0.0616(19) -0.0121(16) 0.0043(14) -0.0059(15) C14 0.0320(17) 0.051(2) 0.0521(17) -0.0059(15) 0.0012(14) 0.0078(14) C15 0.0344(16) 0.0425(17) 0.0475(16) -0.0013(14) 0.0012(13) 0.0091(14) C16 0.0326(16) 0.055(2) 0.0561(18) 0.0043(16) -0.0027(14) -0.0024(15) C20 0.058(2) 0.057(2) 0.0456(17) -0.0056(16) 0.0051(16) 0.0068(18) C21 0.062(2) 0.058(2) 0.059(2) 0.0098(18) -0.0204(18) 0.0007(19) C22 0.058(2) 0.053(2) 0.078(3) 0.0073(19) 0.0077(19) 0.0001(18) C23 0.0356(18) 0.073(3) 0.076(2) 0.003(2) -0.0037(17) 0.0053(19) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.373(4) . ? O1 H1 0.90(4) . ? O2 C15 1.367(4) . ? O2 H2 0.90(5) . ? N8 C7 1.472(4) . ? N8 C9 1.473(4) . ? N8 C16 1.481(4) . ? C1 C2 1.395(4) . ? C1 C6 1.403(4) . ? C2 C3 1.382(5) . ? C2 C21 1.509(4) . ? C3 C4 1.389(4) . ? C3 H3 0.95 . ? C4 C5 1.394(4) . ? C4 C20 1.502(4) . ? C5 C6 1.387(4) . ? C5 H5 0.95 . ? C6 C7 1.497(4) . ? C7 H7A 0.99 . ? C7 H7B 0.99 . ? C9 C10 1.502(4) . ? C9 H9A 0.99 . ? C9 H9B 0.99 . ? C10 C11 1.384(4) . ? C10 C15 1.398(4) . ? C11 C12 1.393(4) . ? C11 H11 0.95 . ? C12 C13 1.385(5) . ? C12 C22 1.506(5) . ? C13 C14 1.395(5) . ? C13 H13 0.95 . ? C14 C15 1.397(4) . ? C14 C23 1.511(5) . ? C16 C17A 1.494(9) . ? C16 C17B 1.564(8) . ? C16 H16A 0.99 . ? C16 H16B 0.99 . ? C17A C18A 1.521(13) . ? C17A H17A 0.99 . ? C17A H17B 0.99 . ? C18A C19A 1.482(18) . ? C18A H18A 0.99 . ? C18A H18B 0.99 . ? C19A C19A 1.560(10) 7 ? C19A H19A 0.99 . ? C19A H19B 0.99 . ? C17B C18B 1.548(7) . ? C17B H17C 0.99 . ? C17B H17D 0.99 . ? C18B C19B 1.449(8) . ? C18B H18C 0.99 . ? C18B H18D 0.99 . ? C19B C19B 1.565(17) 7 ? C19B H19C 0.99 . ? C19B H19D 0.99 . ? C20 H20A 0.98 . ? C20 H20B 0.98 . ? C20 H20C 0.98 . ? C21 H21A 0.98 . ? C21 H21B 0.98 . ? C21 H21C 0.98 . ? C22 H22A 0.98 . ? C22 H22B 0.98 . ? C22 H22C 0.98 . ? C23 H23A 0.98 . ? C23 H23B 0.98 . ? C23 H23C 0.98 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 H1 110(3) . . ? C15 O2 H2 110(3) . . ? C7 N8 C9 110.4(2) . . ? C7 N8 C16 109.2(2) . . ? C9 N8 C16 110.9(2) . . ? O1 C1 C2 119.6(3) . . ? O1 C1 C6 119.8(3) . . ? C2 C1 C6 120.6(3) . . ? C3 C2 C1 118.7(3) . . ? C3 C2 C21 121.6(3) . . ? C1 C2 C21 119.7(3) . . ? C2 C3 C4 122.4(3) . . ? C2 C3 H3 118.8 . . ? C4 C3 H3 118.8 . . ? C3 C4 C5 117.5(3) . . ? C3 C4 C20 122.4(3) . . ? C5 C4 C20 120.2(3) . . ? C6 C5 C4 122.2(3) . . ? C6 C5 H5 118.9 . . ? C4 C5 H5 118.9 . . ? C5 C6 C1 118.5(3) . . ? C5 C6 C7 121.0(3) . . ? C1 C6 C7 120.4(3) . . ? N8 C7 C6 113.0(2) . . ? N8 C7 H7A 109 . . ? C6 C7 H7A 109 . . ? N8 C7 H7B 109 . . ? C6 C7 H7B 109 . . ? H7A C7 H7B 107.8 . . ? N8 C9 C10 112.9(2) . . ? N8 C9 H9A 109 . . ? C10 C9 H9A 109 . . ? N8 C9 H9B 109 . . ? C10 C9 H9B 109 . . ? H9A C9 H9B 107.8 . . ? C11 C10 C15 118.6(3) . . ? C11 C10 C9 120.8(3) . . ? C15 C10 C9 120.6(3) . . ? C10 C11 C12 122.3(3) . . ? C10 C11 H11 118.8 . . ? C12 C11 H11 118.8 . . ? C13 C12 C11 117.4(3) . . ? C13 C12 C22 121.6(3) . . ? C11 C12 C22 121.0(3) . . ? C12 C13 C14 122.7(3) . . ? C12 C13 H13 118.6 . . ? C14 C13 H13 118.6 . . ? C13 C14 C15 117.9(3) . . ? C13 C14 C23 119.6(3) . . ? C15 C14 C23 122.4(3) . . ? O2 C15 C14 123.6(3) . . ? O2 C15 C10 115.4(3) . . ? C14 C15 C10 121.0(3) . . ? N8 C16 C17A 115.4(4) . . ? N8 C16 C17B 113.6(4) . . ? C17A C16 C17B 23.0(3) . . ? N8 C16 H16A 108.4 . . ? C17A C16 H16A 108.4 . . ? C17B C16 H16A 127.1 . . ? N8 C16 H16B 108.4 . . ? C17A C16 H16B 108.4 . . ? C17B C16 H16B 88.5 . . ? H16A C16 H16B 107.5 . . ? C16 C17A C18A 113.2(7) . . ? C16 C17A H17A 108.9 . . ? C18A C17A H17A 108.9 . . ? C16 C17A H17B 108.9 . . ? C18A C17A H17B 108.9 . . ? H17A C17A H17B 107.7 . . ? C19A C18A C17A 134.6(10) . . ? C19A C18A H18A 103.6 . . ? C17A C18A H18A 103.6 . . ? C19A C18A H18B 103.6 . . ? C17A C18A H18B 103.6 . . ? H18A C18A H18B 105.3 . . ? C18A C19A C19A 95.4(13) . 7 ? C18A C19A H19A 112.7 . . ? C19A C19A H19A 112.7 7 . ? C18A C19A H19B 112.7 . . ? C19A C19A H19B 112.7 7 . ? H19A C19A H19B 110.2 . . ? C18B C17B C16 117.0(5) . . ? C18B C17B H17C 108.1 . . ? C16 C17B H17C 108.1 . . ? C18B C17B H17D 108.1 . . ? C16 C17B H17D 108.1 . . ? H17C C17B H17D 107.3 . . ? C19B C18B C17B 114.5(7) . . ? C19B C18B H18C 108.6 . . ? C17B C18B H18C 108.6 . . ? C19B C18B H18D 108.6 . . ? C17B C18B H18D 108.6 . . ? H18C C18B H18D 107.6 . . ? C18B C19B C19B 116.0(7) . 7 ? C18B C19B H19C 108.3 . . ? C19B C19B H19C 108.3 7 . ? C18B C19B H19D 108.3 . . ? C19B C19B H19D 108.3 7 . ? H19C C19B H19D 107.4 . . ? C4 C20 H20A 109.5 . . ? C4 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C4 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C2 C21 H21A 109.5 . . ? C2 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C2 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C12 C22 H22A 109.5 . . ? C12 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C12 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C14 C23 H23A 109.5 . . ? C14 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C14 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 178.1(3) . . . . ? C6 C1 C2 C3 -1.4(5) . . . . ? O1 C1 C2 C21 -2.1(5) . . . . ? C6 C1 C2 C21 178.4(3) . . . . ? C1 C2 C3 C4 2.2(5) . . . . ? C21 C2 C3 C4 -177.5(3) . . . . ? C2 C3 C4 C5 -0.8(5) . . . . ? C2 C3 C4 C20 180.0(3) . . . . ? C3 C4 C5 C6 -1.5(5) . . . . ? C20 C4 C5 C6 177.8(3) . . . . ? C4 C5 C6 C1 2.2(5) . . . . ? C4 C5 C6 C7 -173.6(3) . . . . ? O1 C1 C6 C5 179.7(3) . . . . ? C2 C1 C6 C5 -0.7(4) . . . . ? O1 C1 C6 C7 -4.5(5) . . . . ? C2 C1 C6 C7 175.0(3) . . . . ? C9 N8 C7 C6 -164.4(2) . . . . ? C16 N8 C7 C6 73.4(3) . . . . ? C5 C6 C7 N8 -139.8(3) . . . . ? C1 C6 C7 N8 44.5(4) . . . . ? C7 N8 C9 C10 60.5(3) . . . . ? C16 N8 C9 C10 -178.3(2) . . . . ? N8 C9 C10 C11 -107.6(3) . . . . ? N8 C9 C10 C15 71.4(3) . . . . ? C15 C10 C11 C12 -1.3(4) . . . . ? C9 C10 C11 C12 177.7(3) . . . . ? C10 C11 C12 C13 0.6(5) . . . . ? C10 C11 C12 C22 -178.8(3) . . . . ? C11 C12 C13 C14 0.6(5) . . . . ? C22 C12 C13 C14 179.9(3) . . . . ? C12 C13 C14 C15 -1.0(5) . . . . ? C12 C13 C14 C23 178.8(3) . . . . ? C13 C14 C15 O2 -179.9(3) . . . . ? C23 C14 C15 O2 0.3(5) . . . . ? C13 C14 C15 C10 0.3(5) . . . . ? C23 C14 C15 C10 -179.5(3) . . . . ? C11 C10 C15 O2 -179.0(3) . . . . ? C9 C10 C15 O2 1.9(4) . . . . ? C11 C10 C15 C14 0.8(4) . . . . ? C9 C10 C15 C14 -178.2(3) . . . . ? C7 N8 C16 C17A 175.0(4) . . . . ? C9 N8 C16 C17A 53.2(5) . . . . ? C7 N8 C16 C17B -159.7(4) . . . . ? C9 N8 C16 C17B 78.4(4) . . . . ? N8 C16 C17A C18A 57.4(8) . . . . ? C16 C17A C18A C19A 169.5(11) . . . . ? C17A C18A C19A C19A -129.3(12) . . . 7 ? N8 C16 C17B C18B 67.8(6) . . . . ? C16 C17B C18B C19B 169.2(6) . . . . ? C17B C18B C19B C19B 70.5(11) . . . 7 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 N8 0.90(4) 1.90(4) 2.685(3) 145(4) . O2 H2 O1 0.90(5) 1.98(5) 2.792(3) 148(4) 7 # END of CIF data_H4L3_3 _database_code_depnum_ccdc_archive 'CCDC 888653' #TrackingRef '- New_All_cifs.cif' _audit_creation_date 2012-06-04T15:55:07-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C42 H56 N2 O6, C4 H10 O' _chemical_formula_sum 'C46 H66 N2 O7' _chemical_formula_weight 759.01 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_Int_Tables_number 15 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 25.4087(12) _cell_length_b 12.1422(5) _cell_length_c 15.9143(7) _cell_angle_alpha 90 _cell_angle_beta 113.402(2) _cell_angle_gamma 90 _cell_volume 4506.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 4866 _cell_measurement_theta_min 0.407 _cell_measurement_theta_max 26.733 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.119 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1648 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0338 _diffrn_reflns_av_unetI/netI 0.0389 _diffrn_reflns_number 8379 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.49 _diffrn_reflns_theta_max 25.99 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _reflns_number_total 4411 _reflns_number_gt 2847 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1019P)^2^+2.5142P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 4411 _refine_ls_number_parameters 260 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.1048 _refine_ls_R_factor_gt 0.0661 _refine_ls_wR_factor_ref 0.2044 _refine_ls_wR_factor_gt 0.1741 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.066 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.41 _refine_diff_density_min -0.29 _refine_diff_density_rms 0.036 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.31606(8) 0.59847(15) 0.34055(12) 0.0639(5) Uani 1 1 d . . . H1 H 0.2846(13) 0.551(2) 0.3249(19) 0.077 Uiso 1 1 d . . . O2 O 0.20876(8) 0.51548(15) 0.40910(12) 0.0682(5) Uani 1 1 d . . . H2 H 0.2227(13) 0.459(3) 0.393(2) 0.082 Uiso 1 1 d . . . O3 O 0 0.3639(4) 0.25 0.1322(14) Uani 1 2 d S . . O18 O 0.25517(8) 0.30186(14) 0.39868(13) 0.0694(5) Uani 1 1 d . . . N8 N 0.23858(9) 0.43832(16) 0.24536(13) 0.0580(5) Uani 1 1 d . . . C1 C 0.33853(10) 0.58251(19) 0.27613(17) 0.0561(6) Uani 1 1 d . . . C2 C 0.39426(11) 0.6190(2) 0.29545(18) 0.0646(7) Uani 1 1 d . . . C3 C 0.41667(12) 0.6016(2) 0.2306(2) 0.0731(8) Uani 1 1 d . . . H3 H 0.4537 0.6279 0.2425 0.088 Uiso 1 1 calc R . . C4 C 0.38720(11) 0.5471(2) 0.14879(18) 0.0657(7) Uani 1 1 d . . . C5 C 0.33157(11) 0.5134(2) 0.13062(17) 0.0602(6) Uani 1 1 d . . . H5 H 0.3104 0.4772 0.0752 0.072 Uiso 1 1 calc R . . C6 C 0.30651(10) 0.53204(19) 0.19269(16) 0.0549(6) Uani 1 1 d . . . C7 C 0.24505(11) 0.5000(2) 0.17031(17) 0.0629(7) Uani 1 1 d . . . H7A H 0.2214 0.5666 0.1578 0.076 Uiso 1 1 calc R . . H7B H 0.2311 0.4547 0.1148 0.076 Uiso 1 1 calc R . . C9 C 0.17701(11) 0.4259(2) 0.22663(19) 0.0679(7) Uani 1 1 d . . . H9A H 0.1724 0.3658 0.2642 0.081 Uiso 1 1 calc R . . H9B H 0.1561 0.4059 0.1622 0.081 Uiso 1 1 calc R . . C10 C 0.15145(10) 0.5295(2) 0.24654(18) 0.0635(7) Uani 1 1 d . . . C11 C 0.10936(12) 0.5880(3) 0.1768(2) 0.0836(9) Uani 1 1 d . . . H11 H 0.0974 0.5627 0.1163 0.1 Uiso 1 1 calc R . . C12 C 0.08439(14) 0.6827(3) 0.1937(3) 0.0953(11) Uani 1 1 d . . . C13 C 0.10298(14) 0.7188(3) 0.2827(3) 0.0862(9) Uani 1 1 d . . . H13 H 0.0869 0.7833 0.2951 0.103 Uiso 1 1 calc R . . C14 C 0.14470(12) 0.6634(2) 0.3553(2) 0.0704(7) Uani 1 1 d . . . C15 C 0.16849(10) 0.5685(2) 0.33569(18) 0.0599(6) Uani 1 1 d . . . C16 C 0.26939(13) 0.3320(2) 0.2618(2) 0.0717(8) Uani 1 1 d . . . H16A H 0.2983 0.3346 0.2356 0.086 Uiso 1 1 calc R . . H16B H 0.2422 0.2731 0.231 0.086 Uiso 1 1 calc R . . C17 C 0.29789(13) 0.3069(2) 0.3616(2) 0.0724(8) Uani 1 1 d . . . H17A H 0.3181 0.2364 0.3708 0.087 Uiso 1 1 calc R . . H17B H 0.3259 0.3645 0.3928 0.087 Uiso 1 1 calc R . . C19 C 0.27448(12) 0.2498(2) 0.48558(18) 0.0645(7) Uani 1 1 d . . . H19A H 0.3071 0.29 0.53 0.077 Uiso 1 1 calc R . . H19B H 0.2866 0.1741 0.4814 0.077 Uiso 1 1 calc R . . C20 C 0.42846(13) 0.6760(3) 0.3851(2) 0.0862(9) Uani 1 1 d . . . H20A H 0.4455 0.6213 0.4326 0.129 Uiso 1 1 calc R . . H20B H 0.4033 0.7234 0.4015 0.129 Uiso 1 1 calc R . . H20C H 0.4585 0.7199 0.3786 0.129 Uiso 1 1 calc R . . C21 C 0.41442(15) 0.5257(3) 0.0807(2) 0.0919(10) Uani 1 1 d . . . H21A H 0.4243 0.5953 0.0608 0.138 Uiso 1 1 calc R . . H21B H 0.3875 0.4864 0.0282 0.138 Uiso 1 1 calc R . . H21C H 0.4488 0.4817 0.1097 0.138 Uiso 1 1 calc R . . C22 C 0.03872(19) 0.7448(5) 0.1150(3) 0.152(2) Uani 1 1 d . . . H22A H 0.054 0.7653 0.0703 0.228 Uiso 1 1 calc R . . H22B H 0.0276 0.8106 0.1385 0.228 Uiso 1 1 calc R . . H22C H 0.0055 0.6979 0.0863 0.228 Uiso 1 1 calc R . . C23 C 0.16249(16) 0.7027(3) 0.4517(2) 0.0932(10) Uani 1 1 d . . . H23A H 0.145 0.7737 0.4518 0.14 Uiso 1 1 calc R . . H23B H 0.2039 0.7099 0.4799 0.14 Uiso 1 1 calc R . . H23C H 0.1501 0.6501 0.486 0.14 Uiso 1 1 calc R . . C24 C 0.0340(2) 0.4322(5) 0.3214(4) 0.159(2) Uani 1 1 d D . . H24A H 0.0094 0.4728 0.345 0.19 Uiso 1 1 calc R . . H24B H 0.0535 0.486 0.2978 0.19 Uiso 1 1 calc R . . C25 C 0.0749(3) 0.3732(5) 0.3928(4) 0.176(2) Uani 1 1 d DU . . H25A H 0.0561 0.3152 0.4126 0.263 Uiso 1 1 calc R . . H25B H 0.0945 0.4225 0.4437 0.263 Uiso 1 1 calc R . . H25C H 0.1025 0.341 0.3719 0.263 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 O1 0.0628(11) 0.0680(11) 0.0627(11) -0.0041(8) 0.0269(9) -0.0037(8) O2 0.0727(12) 0.0609(11) 0.0643(11) 0.0086(9) 0.0200(9) 0.0139(9) O3 0.090(3) 0.138(3) 0.138(3) 0 0.012(2) 0 O18 0.0832(12) 0.0584(10) 0.0767(12) 0.0156(9) 0.0424(10) 0.0132(9) N8 0.0632(12) 0.0531(11) 0.0608(12) 0.0034(9) 0.0280(10) -0.0067(9) C1 0.0555(13) 0.0524(13) 0.0599(14) 0.0052(11) 0.0224(12) 0.0016(11) C2 0.0540(14) 0.0683(16) 0.0668(16) 0.0011(12) 0.0191(12) -0.0015(12) C3 0.0518(14) 0.0873(19) 0.0793(19) 0.0043(15) 0.0251(14) -0.0045(13) C4 0.0635(15) 0.0717(16) 0.0672(16) 0.0112(13) 0.0315(13) 0.0023(13) C5 0.0645(15) 0.0609(14) 0.0553(14) 0.0069(11) 0.0241(12) -0.0041(11) C6 0.0548(13) 0.0534(13) 0.0543(13) 0.0109(11) 0.0192(11) -0.0037(10) C7 0.0592(15) 0.0739(16) 0.0543(14) 0.0050(12) 0.0210(12) -0.0133(12) C9 0.0639(16) 0.0759(17) 0.0647(15) 0.0023(13) 0.0264(13) -0.0179(13) C10 0.0497(13) 0.0731(16) 0.0691(17) 0.0173(13) 0.0250(12) -0.0062(12) C11 0.0582(16) 0.124(3) 0.0674(18) 0.0284(17) 0.0242(14) -0.0006(17) C12 0.0654(18) 0.124(3) 0.098(3) 0.054(2) 0.0345(18) 0.0272(19) C13 0.078(2) 0.083(2) 0.108(3) 0.0374(19) 0.0480(19) 0.0233(16) C14 0.0630(15) 0.0623(15) 0.090(2) 0.0209(14) 0.0353(15) 0.0075(13) C15 0.0513(13) 0.0597(14) 0.0674(16) 0.0180(12) 0.0222(12) 0.0020(11) C16 0.092(2) 0.0529(14) 0.0860(19) -0.0036(13) 0.0522(17) -0.0067(13) C17 0.0810(18) 0.0520(14) 0.098(2) 0.0138(13) 0.0505(17) 0.0088(13) C19 0.0777(17) 0.0454(13) 0.0713(16) 0.0062(11) 0.0307(13) 0.0082(12) C20 0.0650(17) 0.103(2) 0.079(2) -0.0132(17) 0.0165(15) -0.0146(16) C21 0.086(2) 0.112(3) 0.094(2) 0.0015(19) 0.0536(19) -0.0015(18) C22 0.104(3) 0.218(6) 0.128(3) 0.091(4) 0.039(3) 0.074(3) C23 0.104(2) 0.076(2) 0.100(2) -0.0043(18) 0.042(2) 0.0127(18) C24 0.121(4) 0.162(5) 0.185(6) 0.010(4) 0.053(4) -0.028(4) C25 0.159(5) 0.170(5) 0.163(5) 0.039(4) 0.027(4) -0.043(4) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.371(3) . ? O1 H1 0.94(3) . ? O2 C15 1.370(3) . ? O2 H2 0.86(3) . ? O3 C24 1.395(6) . ? O3 C24 1.395(6) 2 ? O18 C19 1.419(3) . ? O18 C17 1.428(3) . ? N8 C7 1.473(3) . ? N8 C16 1.478(3) . ? N8 C9 1.479(3) . ? C1 C6 1.394(3) . ? C1 C2 1.397(3) . ? C2 C3 1.379(4) . ? C2 C20 1.511(4) . ? C3 C4 1.385(4) . ? C3 H3 0.94 . ? C4 C5 1.387(4) . ? C4 C21 1.521(4) . ? C5 C6 1.390(3) . ? C5 H5 0.94 . ? C6 C7 1.508(3) . ? C7 H7A 0.98 . ? C7 H7B 0.98 . ? C9 C10 1.506(4) . ? C9 H9A 0.98 . ? C9 H9B 0.98 . ? C10 C15 1.392(4) . ? C10 C11 1.392(4) . ? C11 C12 1.390(5) . ? C11 H11 0.94 . ? C12 C13 1.375(5) . ? C12 C22 1.525(5) . ? C13 C14 1.392(4) . ? C13 H13 0.94 . ? C14 C15 1.393(4) . ? C14 C23 1.495(4) . ? C16 C17 1.493(4) . ? C16 H16A 0.98 . ? C16 H16B 0.98 . ? C17 H17A 0.98 . ? C17 H17B 0.98 . ? C19 C19 1.487(5) 7_556 ? C19 H19A 0.98 . ? C19 H19B 0.98 . ? C20 H20A 0.97 . ? C20 H20B 0.97 . ? C20 H20C 0.97 . ? C21 H21A 0.97 . ? C21 H21B 0.97 . ? C21 H21C 0.97 . ? C22 H22A 0.97 . ? C22 H22B 0.97 . ? C22 H22C 0.97 . ? C23 H23A 0.97 . ? C23 H23B 0.97 . ? C23 H23C 0.97 . ? C24 C25 1.395(6) . ? C24 H24A 0.98 . ? C24 H24B 0.98 . ? C25 H25A 0.97 . ? C25 H25B 0.97 . ? C25 H25C 0.97 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 H1 106.1(17) . . ? C15 O2 H2 112(2) . . ? C24 O3 C24 107.1(6) . 2 ? C19 O18 C17 113.4(2) . . ? C7 N8 C16 111.44(19) . . ? C7 N8 C9 109.76(19) . . ? C16 N8 C9 113.0(2) . . ? O1 C1 C6 121.0(2) . . ? O1 C1 C2 118.5(2) . . ? C6 C1 C2 120.4(2) . . ? C3 C2 C1 118.1(2) . . ? C3 C2 C20 121.5(2) . . ? C1 C2 C20 120.4(2) . . ? C2 C3 C4 123.2(2) . . ? C2 C3 H3 118.4 . . ? C4 C3 H3 118.4 . . ? C3 C4 C5 117.6(2) . . ? C3 C4 C21 121.5(3) . . ? C5 C4 C21 121.0(3) . . ? C4 C5 C6 121.3(2) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? C5 C6 C1 119.3(2) . . ? C5 C6 C7 120.9(2) . . ? C1 C6 C7 119.8(2) . . ? N8 C7 C6 112.2(2) . . ? N8 C7 H7A 109.2 . . ? C6 C7 H7A 109.2 . . ? N8 C7 H7B 109.2 . . ? C6 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? N8 C9 C10 112.5(2) . . ? N8 C9 H9A 109.1 . . ? C10 C9 H9A 109.1 . . ? N8 C9 H9B 109.1 . . ? C10 C9 H9B 109.1 . . ? H9A C9 H9B 107.8 . . ? C15 C10 C11 117.9(3) . . ? C15 C10 C9 120.9(2) . . ? C11 C10 C9 121.2(3) . . ? C12 C11 C10 122.3(3) . . ? C12 C11 H11 118.9 . . ? C10 C11 H11 118.9 . . ? C13 C12 C11 117.7(3) . . ? C13 C12 C22 121.8(4) . . ? C11 C12 C22 120.5(4) . . ? C12 C13 C14 122.6(3) . . ? C12 C13 H13 118.7 . . ? C14 C13 H13 118.7 . . ? C13 C14 C15 117.9(3) . . ? C13 C14 C23 121.2(3) . . ? C15 C14 C23 120.9(3) . . ? O2 C15 C10 122.3(2) . . ? O2 C15 C14 116.2(2) . . ? C10 C15 C14 121.5(2) . . ? N8 C16 C17 111.4(2) . . ? N8 C16 H16A 109.3 . . ? C17 C16 H16A 109.3 . . ? N8 C16 H16B 109.3 . . ? C17 C16 H16B 109.3 . . ? H16A C16 H16B 108 . . ? O18 C17 C16 108.7(2) . . ? O18 C17 H17A 109.9 . . ? C16 C17 H17A 109.9 . . ? O18 C17 H17B 109.9 . . ? C16 C17 H17B 109.9 . . ? H17A C17 H17B 108.3 . . ? O18 C19 C19 106.9(3) . 7_556 ? O18 C19 H19A 110.3 . . ? C19 C19 H19A 110.3 7_556 . ? O18 C19 H19B 110.3 . . ? C19 C19 H19B 110.3 7_556 . ? H19A C19 H19B 108.6 . . ? C2 C20 H20A 109.5 . . ? C2 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C2 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C4 C21 H21A 109.5 . . ? C4 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C4 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C12 C22 H22A 109.5 . . ? C12 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C12 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C14 C23 H23A 109.5 . . ? C14 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C14 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? O3 C24 C25 112.3(5) . . ? O3 C24 H24A 109.2 . . ? C25 C24 H24A 109.2 . . ? O3 C24 H24B 109.2 . . ? C25 C24 H24B 109.2 . . ? H24A C24 H24B 107.9 . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 179.3(2) . . . . ? C6 C1 C2 C3 -1.3(4) . . . . ? O1 C1 C2 C20 -0.7(4) . . . . ? C6 C1 C2 C20 178.6(3) . . . . ? C1 C2 C3 C4 -1.8(4) . . . . ? C20 C2 C3 C4 178.2(3) . . . . ? C2 C3 C4 C5 2.9(4) . . . . ? C2 C3 C4 C21 -177.6(3) . . . . ? C3 C4 C5 C6 -0.9(4) . . . . ? C21 C4 C5 C6 179.6(3) . . . . ? C4 C5 C6 C1 -2.1(4) . . . . ? C4 C5 C6 C7 177.0(2) . . . . ? O1 C1 C6 C5 -177.5(2) . . . . ? C2 C1 C6 C5 3.2(4) . . . . ? O1 C1 C6 C7 3.4(3) . . . . ? C2 C1 C6 C7 -175.9(2) . . . . ? C16 N8 C7 C6 -63.8(3) . . . . ? C9 N8 C7 C6 170.3(2) . . . . ? C5 C6 C7 N8 131.8(2) . . . . ? C1 C6 C7 N8 -49.1(3) . . . . ? C7 N8 C9 C10 -77.6(3) . . . . ? C16 N8 C9 C10 157.4(2) . . . . ? N8 C9 C10 C15 -66.8(3) . . . . ? N8 C9 C10 C11 114.4(3) . . . . ? C15 C10 C11 C12 0.0(4) . . . . ? C9 C10 C11 C12 178.8(3) . . . . ? C10 C11 C12 C13 0.6(5) . . . . ? C10 C11 C12 C22 179.5(3) . . . . ? C11 C12 C13 C14 -0.9(5) . . . . ? C22 C12 C13 C14 -179.8(3) . . . . ? C12 C13 C14 C15 0.6(4) . . . . ? C12 C13 C14 C23 -177.9(3) . . . . ? C11 C10 C15 O2 178.7(2) . . . . ? C9 C10 C15 O2 -0.1(3) . . . . ? C11 C10 C15 C14 -0.4(4) . . . . ? C9 C10 C15 C14 -179.2(2) . . . . ? C13 C14 C15 O2 -179.1(2) . . . . ? C23 C14 C15 O2 -0.6(4) . . . . ? C13 C14 C15 C10 0.1(4) . . . . ? C23 C14 C15 C10 178.5(2) . . . . ? C7 N8 C16 C17 140.6(2) . . . . ? C9 N8 C16 C17 -95.2(3) . . . . ? C19 O18 C17 C16 163.8(2) . . . . ? N8 C16 C17 O18 59.8(3) . . . . ? C17 O18 C19 C19 -179.6(2) . . . 7_556 ? C24 O3 C24 C25 -172.7(6) 2 . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 N8 0.94(3) 1.91(3) 2.754(3) 148(2) . O2 H2 O18 0.86(3) 2.07(3) 2.881(3) 158(3) . # END of CIF data_H4L4_4 _database_code_depnum_ccdc_archive 'CCDC 888654' #TrackingRef '- New_All_cifs.cif' _audit_creation_date 2012-06-05T12:00:27-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C54 H80 N2 O6' _chemical_formula_sum 'C54 H80 N2 O6' _chemical_formula_weight 853.2 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_Int_Tables_number 15 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 26.531(5) _cell_length_b 8.0890(16) _cell_length_c 25.787(5) _cell_angle_alpha 90 _cell_angle_beta 114.46(3) _cell_angle_gamma 90 _cell_volume 5037.6(20) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 40772 _cell_measurement_theta_min 0.407 _cell_measurement_theta_max 28.7 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.32 _exptl_crystal_density_diffrn 1.125 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1864 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_T_min 0.974 _exptl_absorpt_correction_T_max 0.977 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 2008)' #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Bruker AXS Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.21302E-2 _diffrn_orient_matrix_ub_12 -0.873503E-1 _diffrn_orient_matrix_ub_13 0.264502E-1 _diffrn_orient_matrix_ub_21 -0.95378E-2 _diffrn_orient_matrix_ub_22 0.860268E-1 _diffrn_orient_matrix_ub_23 0.223088E-1 _diffrn_orient_matrix_ub_31 -0.402084E-1 _diffrn_orient_matrix_ub_32 -0.157787E-1 _diffrn_orient_matrix_ub_33 -0.247977E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0571 _diffrn_reflns_av_unetI/netI 0.0676 _diffrn_reflns_number 17419 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 2.66 _diffrn_reflns_theta_max 25 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _reflns_number_total 4432 _reflns_number_gt 3071 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SIR92 (Giacovazzo et al, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0627P)^2^+7.2279P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 4432 _refine_ls_number_parameters 297 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1039 _refine_ls_R_factor_gt 0.0684 _refine_ls_wR_factor_ref 0.1661 _refine_ls_wR_factor_gt 0.1509 _refine_ls_goodness_of_fit_ref 1.05 _refine_ls_restrained_S_all 1.05 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.306 _refine_diff_density_min -0.214 _refine_diff_density_rms 0.049 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 O18 O 0.02962(8) 0.5339(2) -0.28487(8) 0.0335(5) Uani 1 1 d . . . O1 O -0.06442(8) 0.3336(2) -0.34293(9) 0.0338(5) Uani 1 1 d . . . O2 O 0.14596(8) 0.0024(3) -0.34158(8) 0.0349(5) Uani 1 1 d . . . N8 N 0.09031(9) 0.2219(3) -0.30533(9) 0.0254(5) Uani 1 1 d . . . C6 C -0.00561(10) 0.1123(3) -0.35064(11) 0.0233(6) Uani 1 1 d . . . C4 C -0.04293(10) -0.0749(3) -0.43240(11) 0.0250(6) Uani 1 1 d . . . C7 C 0.04312(10) 0.1535(3) -0.29560(11) 0.0258(6) Uani 1 1 d . . . H7A H 0.0314 0.235 -0.2741 0.031 Uiso 1 1 calc R . . H7B H 0.0553 0.0522 -0.2721 0.031 Uiso 1 1 calc R . . C26 C -0.03788(11) -0.2299(3) -0.46460(12) 0.0280(6) Uani 1 1 d . . . C1 C -0.05535(11) 0.1998(3) -0.37095(12) 0.0257(6) Uani 1 1 d . . . C2 C -0.09952(11) 0.1508(3) -0.42104(12) 0.0306(7) Uani 1 1 d . . . C13 C 0.21211(11) -0.2780(4) -0.22186(13) 0.0328(7) Uani 1 1 d . . . H13 H 0.2306 -0.3816 -0.2142 0.039 Uiso 1 1 calc R . . C14 C 0.19218(10) -0.2153(4) -0.27721(12) 0.0315(7) Uani 1 1 d . . . C10 C 0.16279(10) 0.0315(3) -0.24288(12) 0.0298(7) Uani 1 1 d . . . C5 C -0.00056(11) -0.0224(3) -0.38216(11) 0.0252(6) Uani 1 1 d . . . H5 H 0.0336 -0.0806 -0.3684 0.03 Uiso 1 1 calc R . . C9 C 0.14222(11) 0.2082(3) -0.25315(12) 0.0310(7) Uani 1 1 d . . . H9A H 0.1357 0.2475 -0.2201 0.037 Uiso 1 1 calc R . . H9B H 0.1709 0.2795 -0.2568 0.037 Uiso 1 1 calc R . . C21 C 0.22639(12) -0.2661(4) -0.11727(13) 0.0405(8) Uani 1 1 d . . . C3 C -0.09244(11) 0.0154(3) -0.45076(12) 0.0312(7) Uani 1 1 d . . . H3 H -0.1225 -0.0173 -0.485 0.037 Uiso 1 1 calc R . . C12 C 0.20614(11) -0.1957(4) -0.17752(12) 0.0343(7) Uani 1 1 d . . . C11 C 0.18132(11) -0.0398(4) -0.18944(12) 0.0331(7) Uani 1 1 d . . . H11 H 0.177 0.0194 -0.1597 0.04 Uiso 1 1 calc R . . C25 C -0.15356(12) 0.2450(4) -0.44282(14) 0.0433(8) Uani 1 1 d . . . H25A H -0.1689 0.2421 -0.4142 0.065 Uiso 1 1 calc R . . H25B H -0.1798 0.194 -0.4781 0.065 Uiso 1 1 calc R . . H25C H -0.147 0.36 -0.4503 0.065 Uiso 1 1 calc R . . C15 C 0.16653(10) -0.0601(3) -0.28732(12) 0.0288(6) Uani 1 1 d . . . C19 C 0.02708(14) 0.6727(3) -0.25194(14) 0.0422(8) Uani 1 1 d . . . H19A H 0.0315 0.7762 -0.2701 0.051 Uiso 1 1 calc R . . H19B H 0.0574 0.6665 -0.2133 0.051 Uiso 1 1 calc R . . C20 C 0.19649(12) -0.3093(4) -0.32516(13) 0.0395(8) Uani 1 1 d . . . H20A H 0.16 -0.3147 -0.3572 0.059 Uiso 1 1 calc R . . H20B H 0.2097 -0.4215 -0.3124 0.059 Uiso 1 1 calc R . . H20C H 0.2226 -0.2531 -0.3373 0.059 Uiso 1 1 calc R . . C16 C 0.08070(12) 0.3886(3) -0.32953(12) 0.0322(7) Uani 1 1 d . . . H16A H 0.0445 0.3886 -0.363 0.039 Uiso 1 1 calc R . . H16B H 0.1095 0.4118 -0.3436 0.039 Uiso 1 1 calc R . . C28 C -0.06524(15) -0.3734(4) -0.44811(15) 0.0495(9) Uani 1 1 d . . . H28A H -0.1047 -0.3496 -0.46 0.074 Uiso 1 1 calc R . . H28B H -0.0476 -0.3888 -0.4067 0.074 Uiso 1 1 calc R . . H28C H -0.0611 -0.4745 -0.467 0.074 Uiso 1 1 calc R . . C17 C 0.08062(12) 0.5301(4) -0.29099(13) 0.0381(7) Uani 1 1 d . . . H17A H 0.1117 0.5165 -0.2531 0.046 Uiso 1 1 calc R . . H17B H 0.0858 0.636 -0.3074 0.046 Uiso 1 1 calc R . . C27 C -0.06521(16) -0.2042(4) -0.52861(14) 0.0541(9) Uani 1 1 d . . . H27A H -0.0637 -0.3073 -0.5479 0.081 Uiso 1 1 calc R . . H27B H -0.0456 -0.117 -0.5392 0.081 Uiso 1 1 calc R . . H27C H -0.1039 -0.1716 -0.54 0.081 Uiso 1 1 calc R . . C29 C 0.02258(13) -0.2745(4) -0.44912(16) 0.0515(9) Uani 1 1 d . . . H29A H 0.0412 -0.298 -0.4082 0.077 Uiso 1 1 calc R . . H29B H 0.0411 -0.1817 -0.4585 0.077 Uiso 1 1 calc R . . H29C H 0.0243 -0.3724 -0.4707 0.077 Uiso 1 1 calc R . . C23 C 0.24890(16) -0.4419(5) -0.11221(17) 0.0670(12) Uani 1 1 d . . . H23A H 0.2199 -0.5148 -0.1381 0.1 Uiso 1 1 calc R . . H23B H 0.2606 -0.4809 -0.073 0.1 Uiso 1 1 calc R . . H23C H 0.2807 -0.4428 -0.1223 0.1 Uiso 1 1 calc R . . C22 C 0.17828(16) -0.2724(5) -0.09922(16) 0.0667(12) Uani 1 1 d . . . H22A H 0.1642 -0.1604 -0.0993 0.1 Uiso 1 1 calc R . . H22B H 0.1912 -0.3191 -0.0608 0.1 Uiso 1 1 calc R . . H22C H 0.1486 -0.3419 -0.1259 0.1 Uiso 1 1 calc R . . C24 C 0.27219(18) -0.1556(6) -0.07702(17) 0.0891(15) Uani 1 1 d . . . H24A H 0.3032 -0.1548 -0.0883 0.134 Uiso 1 1 calc R . . H24B H 0.2849 -0.1979 -0.038 0.134 Uiso 1 1 calc R . . H24C H 0.258 -0.0429 -0.0787 0.134 Uiso 1 1 calc R . . H2 H 0.1200(14) 0.082(4) -0.3405(14) 0.061(11) Uiso 1 1 d . A 2 H1 H -0.0289(18) 0.388(5) -0.3220(18) 0.094(14) Uiso 1 1 d . B 2 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 O18 0.0418(11) 0.0226(10) 0.0374(12) -0.0047(8) 0.0177(10) -0.0049(9) O1 0.0345(11) 0.0257(10) 0.0417(13) -0.0053(9) 0.0162(10) 0.0019(9) O2 0.0343(11) 0.0421(12) 0.0293(12) 0.0048(9) 0.0142(10) 0.0059(10) N8 0.0225(11) 0.0257(12) 0.0255(13) 0.0005(10) 0.0076(10) -0.0042(10) C6 0.0273(14) 0.0194(13) 0.0244(16) 0.0013(11) 0.0118(12) -0.0033(12) C4 0.0267(14) 0.0275(14) 0.0227(15) -0.0005(12) 0.0121(12) -0.0043(12) C7 0.0300(14) 0.0225(13) 0.0260(16) 0.0014(11) 0.0127(13) -0.0012(12) C26 0.0344(15) 0.0247(14) 0.0279(17) -0.0029(12) 0.0158(13) -0.0050(12) C1 0.0276(14) 0.0195(13) 0.0319(17) -0.0032(12) 0.0144(13) -0.0030(12) C2 0.0259(14) 0.0290(15) 0.0354(18) 0.0002(13) 0.0110(14) 0.0005(12) C13 0.0201(14) 0.0386(16) 0.0402(19) 0.0066(14) 0.0129(14) 0.0042(13) C14 0.0166(13) 0.0427(17) 0.0347(18) 0.0012(14) 0.0102(13) -0.0011(13) C10 0.0204(13) 0.0384(16) 0.0269(17) -0.0023(13) 0.0063(12) -0.0028(12) C5 0.0246(13) 0.0236(14) 0.0293(16) 0.0019(12) 0.0131(13) 0.0009(12) C9 0.0242(14) 0.0352(16) 0.0284(17) -0.0055(13) 0.0058(13) -0.0051(13) C21 0.0308(16) 0.058(2) 0.0290(18) 0.0125(15) 0.0091(14) 0.0091(15) C3 0.0267(14) 0.0327(15) 0.0305(16) -0.0025(13) 0.0081(13) -0.0033(13) C12 0.0214(14) 0.0485(18) 0.0321(18) 0.0069(14) 0.0100(13) 0.0011(14) C11 0.0227(14) 0.0450(18) 0.0306(18) -0.0024(14) 0.0100(13) -0.0022(14) C25 0.0294(16) 0.0400(18) 0.053(2) -0.0084(15) 0.0099(16) 0.0035(14) C15 0.0209(13) 0.0383(16) 0.0271(17) 0.0031(13) 0.0099(12) -0.0026(13) C19 0.069(2) 0.0207(14) 0.040(2) -0.0049(13) 0.0261(18) -0.0093(14) C20 0.0331(16) 0.0485(18) 0.041(2) -0.0002(15) 0.0196(15) 0.0035(15) C16 0.0339(16) 0.0303(15) 0.0335(18) 0.0027(13) 0.0151(14) -0.0036(13) C28 0.078(2) 0.0275(16) 0.063(2) -0.0076(15) 0.049(2) -0.0085(17) C17 0.0361(16) 0.0303(16) 0.0440(19) 0.0015(14) 0.0126(15) -0.0081(14) C27 0.084(3) 0.0452(19) 0.032(2) -0.0058(16) 0.0238(19) 0.0049(19) C29 0.0443(19) 0.0446(19) 0.068(3) -0.0258(18) 0.0252(19) -0.0012(16) C23 0.069(3) 0.080(3) 0.064(3) 0.039(2) 0.039(2) 0.030(2) C22 0.062(2) 0.098(3) 0.053(3) 0.030(2) 0.036(2) 0.027(2) C24 0.075(3) 0.114(4) 0.044(3) 0.020(2) -0.009(2) -0.015(3) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O18 C17 1.426(3) . ? O18 C19 1.426(3) . ? O1 C1 1.377(3) . ? O1 H1 0.98(4) . ? O2 C15 1.371(3) . ? O2 H2 0.95(4) . ? N8 C16 1.463(3) . ? N8 C9 1.478(3) . ? N8 C7 1.482(3) . ? C6 C1 1.394(4) . ? C6 C5 1.399(3) . ? C6 C7 1.509(4) . ? C4 C5 1.384(4) . ? C4 C3 1.403(4) . ? C4 C26 1.540(4) . ? C7 H7A 0.99 . ? C7 H7B 0.99 . ? C26 C27 1.517(4) . ? C26 C28 1.520(4) . ? C26 C29 1.527(4) . ? C1 C2 1.395(4) . ? C2 C3 1.394(4) . ? C2 C25 1.511(4) . ? C13 C12 1.387(4) . ? C13 C14 1.396(4) . ? C13 H13 0.95 . ? C14 C15 1.400(4) . ? C14 C20 1.495(4) . ? C10 C11 1.383(4) . ? C10 C15 1.402(4) . ? C10 C9 1.513(4) . ? C5 H5 0.95 . ? C9 H9A 0.99 . ? C9 H9B 0.99 . ? C21 C24 1.519(5) . ? C21 C23 1.527(5) . ? C21 C12 1.528(4) . ? C21 C22 1.530(4) . ? C3 H3 0.95 . ? C12 C11 1.397(4) . ? C11 H11 0.95 . ? C25 H25A 0.98 . ? C25 H25B 0.98 . ? C25 H25C 0.98 . ? C19 C19 1.481(6) 2_554 ? C19 H19A 0.99 . ? C19 H19B 0.99 . ? C20 H20A 0.98 . ? C20 H20B 0.98 . ? C20 H20C 0.98 . ? C16 C17 1.517(4) . ? C16 H16A 0.99 . ? C16 H16B 0.99 . ? C28 H28A 0.98 . ? C28 H28B 0.98 . ? C28 H28C 0.98 . ? C17 H17A 0.99 . ? C17 H17B 0.99 . ? C27 H27A 0.98 . ? C27 H27B 0.98 . ? C27 H27C 0.98 . ? C29 H29A 0.98 . ? C29 H29B 0.98 . ? C29 H29C 0.98 . ? C23 H23A 0.98 . ? C23 H23B 0.98 . ? C23 H23C 0.98 . ? C22 H22A 0.98 . ? C22 H22B 0.98 . ? C22 H22C 0.98 . ? C24 H24A 0.98 . ? C24 H24B 0.98 . ? C24 H24C 0.98 . ? 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 C17 O18 C19 111.3(2) . . ? C1 O1 H1 108(2) . . ? C15 O2 H2 102(2) . . ? C16 N8 C9 113.0(2) . . ? C16 N8 C7 114.0(2) . . ? C9 N8 C7 110.6(2) . . ? C1 C6 C5 118.7(2) . . ? C1 C6 C7 123.4(2) . . ? C5 C6 C7 117.9(2) . . ? C5 C4 C3 116.1(2) . . ? C5 C4 C26 122.4(2) . . ? C3 C4 C26 121.3(2) . . ? N8 C7 C6 112.2(2) . . ? N8 C7 H7A 109.2 . . ? C6 C7 H7A 109.2 . . ? N8 C7 H7B 109.2 . . ? C6 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? C27 C26 C28 109.9(3) . . ? C27 C26 C29 107.1(3) . . ? C28 C26 C29 108.5(3) . . ? C27 C26 C4 111.4(2) . . ? C28 C26 C4 108.2(2) . . ? C29 C26 C4 111.6(2) . . ? O1 C1 C6 123.1(2) . . ? O1 C1 C2 116.5(2) . . ? C6 C1 C2 120.4(2) . . ? C3 C2 C1 118.7(2) . . ? C3 C2 C25 121.0(3) . . ? C1 C2 C25 120.3(2) . . ? C12 C13 C14 123.0(3) . . ? C12 C13 H13 118.5 . . ? C14 C13 H13 118.5 . . ? C13 C14 C15 117.7(3) . . ? C13 C14 C20 122.3(3) . . ? C15 C14 C20 120.0(3) . . ? C11 C10 C15 118.5(3) . . ? C11 C10 C9 121.5(3) . . ? C15 C10 C9 119.9(2) . . ? C4 C5 C6 123.2(2) . . ? C4 C5 H5 118.4 . . ? C6 C5 H5 118.4 . . ? N8 C9 C10 111.3(2) . . ? N8 C9 H9A 109.4 . . ? C10 C9 H9A 109.4 . . ? N8 C9 H9B 109.4 . . ? C10 C9 H9B 109.4 . . ? H9A C9 H9B 108 . . ? C24 C21 C23 108.4(3) . . ? C24 C21 C12 108.7(3) . . ? C23 C21 C12 113.2(3) . . ? C24 C21 C22 110.1(3) . . ? C23 C21 C22 106.8(3) . . ? C12 C21 C22 109.6(2) . . ? C2 C3 C4 123.0(3) . . ? C2 C3 H3 118.5 . . ? C4 C3 H3 118.5 . . ? C13 C12 C11 117.1(3) . . ? C13 C12 C21 123.2(3) . . ? C11 C12 C21 119.7(3) . . ? C10 C11 C12 122.5(3) . . ? C10 C11 H11 118.8 . . ? C12 C11 H11 118.8 . . ? C2 C25 H25A 109.5 . . ? C2 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C2 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? O2 C15 C14 118.6(2) . . ? O2 C15 C10 120.4(2) . . ? C14 C15 C10 121.0(3) . . ? O18 C19 C19 109.1(2) . 2_554 ? O18 C19 H19A 109.9 . . ? C19 C19 H19A 109.9 2_554 . ? O18 C19 H19B 109.9 . . ? C19 C19 H19B 109.9 2_554 . ? H19A C19 H19B 108.3 . . ? C14 C20 H20A 109.5 . . ? C14 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C14 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? N8 C16 C17 117.6(2) . . ? N8 C16 H16A 107.9 . . ? C17 C16 H16A 107.9 . . ? N8 C16 H16B 107.9 . . ? C17 C16 H16B 107.9 . . ? H16A C16 H16B 107.2 . . ? C26 C28 H28A 109.5 . . ? C26 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C26 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? O18 C17 C16 110.3(2) . . ? O18 C17 H17A 109.6 . . ? C16 C17 H17A 109.6 . . ? O18 C17 H17B 109.6 . . ? C16 C17 H17B 109.6 . . ? H17A C17 H17B 108.1 . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C26 C29 H29A 109.5 . . ? C26 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C26 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21 C24 H24A 109.5 . . ? C21 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C21 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 N8 C7 C6 70.5(3) . . . . ? C9 N8 C7 C6 -160.9(2) . . . . ? C1 C6 C7 N8 -110.7(3) . . . . ? C5 C6 C7 N8 70.4(3) . . . . ? C5 C4 C26 C27 -141.8(3) . . . . ? C3 C4 C26 C27 42.3(3) . . . . ? C5 C4 C26 C28 97.3(3) . . . . ? C3 C4 C26 C28 -78.6(3) . . . . ? C5 C4 C26 C29 -22.1(4) . . . . ? C3 C4 C26 C29 162.0(3) . . . . ? C5 C6 C1 O1 179.8(2) . . . . ? C7 C6 C1 O1 0.9(4) . . . . ? C5 C6 C1 C2 1.5(4) . . . . ? C7 C6 C1 C2 -177.4(2) . . . . ? O1 C1 C2 C3 -179.6(2) . . . . ? C6 C1 C2 C3 -1.3(4) . . . . ? O1 C1 C2 C25 1.2(4) . . . . ? C6 C1 C2 C25 179.6(2) . . . . ? C12 C13 C14 C15 1.9(4) . . . . ? C12 C13 C14 C20 -176.9(3) . . . . ? C3 C4 C5 C6 0.0(4) . . . . ? C26 C4 C5 C6 -176.1(2) . . . . ? C1 C6 C5 C4 -0.9(4) . . . . ? C7 C6 C5 C4 178.1(2) . . . . ? C16 N8 C9 C10 -157.0(2) . . . . ? C7 N8 C9 C10 74.0(3) . . . . ? C11 C10 C9 N8 -135.0(3) . . . . ? C15 C10 C9 N8 48.9(3) . . . . ? C1 C2 C3 C4 0.4(4) . . . . ? C25 C2 C3 C4 179.5(3) . . . . ? C5 C4 C3 C2 0.2(4) . . . . ? C26 C4 C3 C2 176.4(2) . . . . ? C14 C13 C12 C11 -3.2(4) . . . . ? C14 C13 C12 C21 178.2(3) . . . . ? C24 C21 C12 C13 115.2(4) . . . . ? C23 C21 C12 C13 -5.3(4) . . . . ? C22 C21 C12 C13 -124.4(3) . . . . ? C24 C21 C12 C11 -63.4(4) . . . . ? C23 C21 C12 C11 176.1(3) . . . . ? C22 C21 C12 C11 57.0(4) . . . . ? C15 C10 C11 C12 3.4(4) . . . . ? C9 C10 C11 C12 -172.7(2) . . . . ? C13 C12 C11 C10 0.5(4) . . . . ? C21 C12 C11 C10 179.2(2) . . . . ? C13 C14 C15 O2 -179.0(2) . . . . ? C20 C14 C15 O2 -0.2(4) . . . . ? C13 C14 C15 C10 2.2(4) . . . . ? C20 C14 C15 C10 -179.0(2) . . . . ? C11 C10 C15 O2 176.5(2) . . . . ? C9 C10 C15 O2 -7.3(4) . . . . ? C11 C10 C15 C14 -4.7(4) . . . . ? C9 C10 C15 C14 171.5(2) . . . . ? C17 O18 C19 C19 178.7(3) . . . 2_554 ? C9 N8 C16 C17 -55.1(3) . . . . ? C7 N8 C16 C17 72.2(3) . . . . ? C19 O18 C17 C16 -176.0(2) . . . . ? N8 C16 C17 O18 -77.3(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2 N8 0.95(4) 1.82(4) 2.711(3) 155(3) . O1 H1 O18 0.98(4) 1.87(4) 2.828(3) 167(4) . # END of CIF data_H4L5_5 _database_code_depnum_ccdc_archive 'CCDC 888655' #TrackingRef '- New_All_cifs.cif' _audit_creation_date 2012-06-05T13:58:35-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C54 H80 N2 O6' _chemical_formula_sum 'C54 H80 N2 O6' _chemical_formula_weight 853.2 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_Int_Tables_number 15 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 14.9930(5) _cell_length_b 17.1820(6) _cell_length_c 20.2780(5) _cell_angle_alpha 90 _cell_angle_beta 104.334(2) _cell_angle_gamma 90 _cell_volume 5061.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 5852 _cell_measurement_theta_min 0.407 _cell_measurement_theta_max 28.7 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.12 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1864 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_T_min 0.974 _exptl_absorpt_correction_T_max 0.977 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 2008)' #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Bruker AXS Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.539508E-1 _diffrn_orient_matrix_ub_12 0.357539E-1 _diffrn_orient_matrix_ub_13 -0.150133E-1 _diffrn_orient_matrix_ub_21 0.284487E-1 _diffrn_orient_matrix_ub_22 0.225427E-1 _diffrn_orient_matrix_ub_23 -0.354659E-1 _diffrn_orient_matrix_ub_31 -0.32148E-1 _diffrn_orient_matrix_ub_32 -0.400536E-1 _diffrn_orient_matrix_ub_33 -0.333624E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0767 _diffrn_reflns_av_unetI/netI 0.0671 _diffrn_reflns_number 24591 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 25 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 4463 _reflns_number_gt 2821 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SIR92 (Giacovazzo et al, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0488P)^2^+3.1474P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 4463 _refine_ls_number_parameters 315 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0997 _refine_ls_R_factor_gt 0.054 _refine_ls_wR_factor_ref 0.131 _refine_ls_wR_factor_gt 0.1143 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.246 _refine_diff_density_min -0.18 _refine_diff_density_rms 0.039 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.65834(15) 0.23544(12) 0.25681(10) 0.0283(5) Uani 1 1 d . . . C2 C 0.72455(14) 0.27960(12) 0.30327(10) 0.0273(5) Uani 1 1 d . . . C3 C 0.71882(16) 0.36028(13) 0.29470(10) 0.0327(5) Uani 1 1 d . . . H3 H 0.7632 0.3916 0.3246 0.039 Uiso 1 1 calc R . . C4 C 0.65158(17) 0.39742(13) 0.24464(11) 0.0369(6) Uani 1 1 d . . . C5 C 0.58822(16) 0.35130(13) 0.20078(11) 0.0348(6) Uani 1 1 d . . . H5 H 0.5419 0.3754 0.1663 0.042 Uiso 1 1 calc R . . C6 C 0.59019(15) 0.27073(13) 0.20547(10) 0.0302(5) Uani 1 1 d . . . C7 C 0.52015(15) 0.22196(14) 0.15728(10) 0.0347(6) Uani 1 1 d . B . H7A H 0.4906 0.1863 0.1838 0.042 Uiso 1 1 calc R . . H7B H 0.4718 0.2563 0.1301 0.042 Uiso 1 1 calc R . . C9 C 0.58771(15) 0.22868(13) 0.06107(10) 0.0310(5) Uani 1 1 d . B . H9A H 0.6281 0.2699 0.0865 0.037 Uiso 1 1 calc R . . H9B H 0.5315 0.2541 0.0335 0.037 Uiso 1 1 calc R . . C10 C 0.63686(14) 0.18888(12) 0.01384(10) 0.0278(5) Uani 1 1 d . . . C11 C 0.61617(15) 0.20973(13) -0.05446(10) 0.0303(5) Uani 1 1 d . . . H11 H 0.5687 0.2465 -0.0711 0.036 Uiso 1 1 calc R . . C12 C 0.66333(16) 0.17804(13) -0.09882(11) 0.0331(6) Uani 1 1 d . . . C13 C 0.73039(16) 0.12290(13) -0.07330(11) 0.0325(5) Uani 1 1 d . . . H13 H 0.7622 0.1003 -0.1036 0.039 Uiso 1 1 calc R . . C14 C 0.75378(15) 0.09865(12) -0.00543(11) 0.0299(5) Uani 1 1 d . . . C15 C 0.70647(14) 0.13454(13) 0.03836(10) 0.0278(5) Uani 1 1 d . . . C16 C 0.49823(17) 0.11278(14) 0.07755(11) 0.0396(6) Uani 1 1 d . B . H16A H 0.5037 0.1057 0.0303 0.048 Uiso 1 1 calc R . . H16B H 0.434 0.1281 0.0757 0.048 Uiso 1 1 calc R . . C17 C 0.5192(2) 0.03736(16) 0.11523(12) 0.0539(7) Uani 1 1 d . . . H17A H 0.4756 -0.0036 0.093 0.065 Uiso 1 1 calc R A 1 H17B H 0.5826 0.0201 0.1164 0.065 Uiso 1 1 calc R A 1 C20 C 0.79803(15) 0.24209(13) 0.36069(10) 0.0316(5) Uani 1 1 d . . . C21 C 0.85956(17) 0.18708(14) 0.33190(12) 0.0414(6) Uani 1 1 d . . . H21A H 0.8212 0.1487 0.302 0.062 Uiso 1 1 calc R . . H21B H 0.9022 0.1602 0.3694 0.062 Uiso 1 1 calc R . . H21C H 0.8947 0.2172 0.3059 0.062 Uiso 1 1 calc R . . C22 C 0.75080(18) 0.19719(16) 0.40850(12) 0.0477(7) Uani 1 1 d . . . H22A H 0.7122 0.233 0.427 0.072 Uiso 1 1 calc R . . H22B H 0.7977 0.1744 0.4459 0.072 Uiso 1 1 calc R . . H22C H 0.7124 0.1557 0.383 0.072 Uiso 1 1 calc R . . C23 C 0.86122(17) 0.30287(15) 0.40426(12) 0.0477(7) Uani 1 1 d . . . H23A H 0.8932 0.3323 0.3757 0.072 Uiso 1 1 calc R . . H23B H 0.9065 0.2766 0.4406 0.072 Uiso 1 1 calc R . . H23C H 0.8243 0.3385 0.4244 0.072 Uiso 1 1 calc R . . C24 C 0.6502(2) 0.48534(14) 0.23896(13) 0.0606(8) Uani 1 1 d . . . H24A H 0.6601 0.5083 0.2844 0.091 Uiso 1 1 calc R . . H24B H 0.5905 0.5023 0.2107 0.091 Uiso 1 1 calc R . . H24C H 0.6992 0.5024 0.218 0.091 Uiso 1 1 calc R . . C25 C 0.82708(16) 0.03571(13) 0.02037(11) 0.0364(6) Uani 1 1 d . . . C26 C 0.86811(19) 0.00460(15) -0.03671(13) 0.0481(7) Uani 1 1 d . . . H26A H 0.819 -0.0178 -0.0729 0.072 Uiso 1 1 calc R . . H26B H 0.9139 -0.0356 -0.0184 0.072 Uiso 1 1 calc R . . H26C H 0.8976 0.0473 -0.0553 0.072 Uiso 1 1 calc R . . C27 C 0.78154(19) -0.03376(14) 0.04739(13) 0.0485(7) Uani 1 1 d . . . H27A H 0.7557 -0.0163 0.0848 0.073 Uiso 1 1 calc R . . H27B H 0.8277 -0.0742 0.0639 0.073 Uiso 1 1 calc R . . H27C H 0.7323 -0.0549 0.0106 0.073 Uiso 1 1 calc R . . C28 C 0.90690(17) 0.06778(16) 0.07647(13) 0.0492(7) Uani 1 1 d . . . H28A H 0.9379 0.1095 0.0578 0.074 Uiso 1 1 calc R . . H28B H 0.9509 0.0259 0.0937 0.074 Uiso 1 1 calc R . . H28C H 0.8829 0.0884 0.1137 0.074 Uiso 1 1 calc R . . C29 C 0.64314(18) 0.20471(15) -0.17214(11) 0.0455(6) Uani 1 1 d . . . H29A H 0.5764 0.2079 -0.1908 0.068 Uiso 1 1 calc R . . H29B H 0.6693 0.1674 -0.1988 0.068 Uiso 1 1 calc R . . H29C H 0.6707 0.2561 -0.1743 0.068 Uiso 1 1 calc R . . N8 N 0.56127(12) 0.17552(10) 0.11043(8) 0.0307(4) Uani 1 1 d . . . O1 O 0.66134(12) 0.15552(9) 0.26380(8) 0.0380(4) Uani 1 1 d . . . O2 O 0.72932(11) 0.11545(10) 0.10658(7) 0.0366(4) Uani 1 1 d . . . O18A O 0.5097(4) 0.0526(3) 0.1841(3) 0.0485(14) Uani 0.712(9) 1 d P B 1 C19A C 0.5297(4) -0.0169(2) 0.2242(2) 0.0487(17) Uani 0.712(9) 1 d P . 1 H19A H 0.5851 -0.0422 0.2157 0.058 Uiso 0.712(9) 1 calc PR B 1 H19B H 0.4776 -0.0537 0.2106 0.058 Uiso 0.712(9) 1 calc PR B 1 O18B O 0.5374(9) 0.0271(8) 0.1856(7) 0.039(3) Uani 0.288(9) 1 d P B 2 C19B C 0.4537(10) 0.0015(6) 0.1999(6) 0.054(4) Uani 0.288(9) 1 d P . 2 H19C H 0.4312 -0.0457 0.1728 0.065 Uiso 0.288(9) 1 calc PR B 2 H19D H 0.4063 0.0425 0.1871 0.065 Uiso 0.288(9) 1 calc PR B 2 H1 H 0.618(2) 0.1350(19) 0.2331(16) 0.085(12) Uiso 1 1 d . . . H2 H 0.6822(19) 0.1343(15) 0.1230(13) 0.059(8) 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 C1 0.0317(13) 0.0304(14) 0.0263(11) -0.0031(9) 0.0142(10) -0.0003(10) C2 0.0261(12) 0.0332(13) 0.0246(11) 0.0001(9) 0.0099(10) 0.0024(10) C3 0.0375(14) 0.0359(14) 0.0248(11) -0.0042(10) 0.0081(10) -0.0009(11) C4 0.0515(16) 0.0336(14) 0.0269(12) -0.0017(10) 0.0122(12) 0.0052(12) C5 0.0397(14) 0.0404(15) 0.0243(12) 0.0026(10) 0.0079(11) 0.0140(12) C6 0.0283(13) 0.0433(15) 0.0216(11) -0.0035(10) 0.0110(10) 0.0019(11) C7 0.0280(13) 0.0512(15) 0.0267(12) -0.0042(10) 0.0100(10) 0.0007(11) C9 0.0293(13) 0.0384(14) 0.0269(12) -0.0019(10) 0.0101(10) -0.0017(10) C10 0.0254(12) 0.0327(13) 0.0264(11) -0.0040(9) 0.0084(9) -0.0076(10) C11 0.0287(12) 0.0336(13) 0.0288(12) 0.0015(9) 0.0075(10) -0.0023(10) C12 0.0357(13) 0.0394(14) 0.0269(12) -0.0035(10) 0.0129(11) -0.0089(11) C13 0.0346(13) 0.0366(14) 0.0304(12) -0.0061(10) 0.0160(11) -0.0065(11) C14 0.0277(12) 0.0311(13) 0.0322(12) -0.0019(10) 0.0102(10) -0.0054(10) C15 0.0255(12) 0.0350(13) 0.0233(11) -0.0017(9) 0.0067(10) -0.0051(10) C16 0.0365(14) 0.0573(17) 0.0268(12) -0.0085(11) 0.0110(11) -0.0154(12) C17 0.0681(19) 0.0578(18) 0.0381(15) -0.0073(13) 0.0174(14) -0.0254(15) C20 0.0303(13) 0.0348(13) 0.0285(12) 0.0005(10) 0.0054(10) 0.0033(10) C21 0.0394(15) 0.0402(15) 0.0432(14) 0.0021(11) 0.0077(12) 0.0082(12) C22 0.0457(16) 0.0669(19) 0.0303(13) 0.0131(12) 0.0089(12) 0.0074(14) C23 0.0390(15) 0.0508(17) 0.0460(15) -0.0071(12) -0.0033(12) 0.0073(13) C24 0.091(2) 0.0374(16) 0.0468(16) 0.0038(12) 0.0052(16) 0.0122(15) C25 0.0381(14) 0.0354(14) 0.0387(13) -0.0024(10) 0.0153(11) 0.0017(11) C26 0.0518(17) 0.0453(16) 0.0549(16) -0.0018(12) 0.0278(14) 0.0076(13) C27 0.0600(17) 0.0391(15) 0.0534(16) 0.0038(12) 0.0273(14) 0.0036(13) C28 0.0370(15) 0.0565(17) 0.0527(16) -0.0029(13) 0.0081(13) 0.0123(13) C29 0.0534(17) 0.0569(17) 0.0288(13) 0.0028(11) 0.0150(12) -0.0020(14) N8 0.0287(10) 0.0420(11) 0.0242(10) -0.0060(8) 0.0117(8) -0.0085(9) O1 0.0419(10) 0.0329(10) 0.0377(10) -0.0010(7) 0.0071(8) -0.0026(8) O2 0.0371(10) 0.0511(11) 0.0232(8) 0.0026(7) 0.0107(7) 0.0071(8) O18A 0.080(4) 0.032(3) 0.044(2) 0.0051(19) 0.035(2) 0.007(2) C19A 0.082(4) 0.029(2) 0.048(3) 0.003(2) 0.041(3) 0.004(2) O18B 0.051(7) 0.034(8) 0.033(4) -0.002(5) 0.013(4) 0.000(5) C19B 0.059(10) 0.034(6) 0.069(8) -0.021(5) 0.018(7) -0.010(6) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.380(3) . ? C1 C6 1.403(3) . ? C1 C2 1.409(3) . ? C2 C3 1.397(3) . ? C2 C20 1.533(3) . ? C3 C4 1.395(3) . ? C3 H3 0.95 . ? C4 C5 1.379(3) . ? C4 C24 1.515(3) . ? C5 C6 1.387(3) . ? C5 H5 0.95 . ? C6 C7 1.501(3) . ? C7 N8 1.486(3) . ? C7 H7A 0.99 . ? C7 H7B 0.99 . ? C9 N8 1.480(3) . ? C9 C10 1.509(3) . ? C9 H9A 0.99 . ? C9 H9B 0.99 . ? C10 C11 1.389(3) . ? C10 C15 1.397(3) . ? C11 C12 1.386(3) . ? C11 H11 0.95 . ? C12 C13 1.385(3) . ? C12 C29 1.513(3) . ? C13 C14 1.397(3) . ? C13 H13 0.95 . ? C14 C15 1.408(3) . ? C14 C25 1.538(3) . ? C15 O2 1.380(2) . ? C16 N8 1.479(3) . ? C16 C17 1.498(4) . ? C16 H16A 0.99 . ? C16 H16B 0.99 . ? C17 O18B 1.396(14) . ? C17 O18A 1.462(6) . ? C17 H17A 0.99 . ? C17 H17B 0.99 . ? C20 C21 1.534(3) . ? C20 C23 1.534(3) . ? C20 C22 1.542(3) . ? C21 H21A 0.98 . ? C21 H21B 0.98 . ? C21 H21C 0.98 . ? C22 H22A 0.98 . ? C22 H22B 0.98 . ? C22 H22C 0.98 . ? C23 H23A 0.98 . ? C23 H23B 0.98 . ? C23 H23C 0.98 . ? C24 H24A 0.98 . ? C24 H24B 0.98 . ? C24 H24C 0.98 . ? C25 C28 1.535(3) . ? C25 C26 1.535(3) . ? C25 C27 1.541(3) . ? C26 H26A 0.98 . ? C26 H26B 0.98 . ? C26 H26C 0.98 . ? C27 H27A 0.98 . ? C27 H27B 0.98 . ? C27 H27C 0.98 . ? C28 H28A 0.98 . ? C28 H28B 0.98 . ? C28 H28C 0.98 . ? C29 H29A 0.98 . ? C29 H29B 0.98 . ? C29 H29C 0.98 . ? O1 H1 0.86(3) . ? O2 H2 0.91(3) . ? O18A C19A 1.434(8) . ? C19A C19B 1.530(12) 2_655 ? C19A H19A 0.99 . ? C19A H19B 0.99 . ? O18B C19B 1.42(2) . ? C19B C19A 1.530(12) 2_655 ? C19B H19C 0.99 . ? C19B H19D 0.99 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C6 120.36(19) . . ? O1 C1 C2 117.9(2) . . ? C6 C1 C2 121.8(2) . . ? C3 C2 C1 116.08(19) . . ? C3 C2 C20 121.48(19) . . ? C1 C2 C20 122.44(19) . . ? C4 C3 C2 123.7(2) . . ? C4 C3 H3 118.1 . . ? C2 C3 H3 118.1 . . ? C5 C4 C3 117.7(2) . . ? C5 C4 C24 122.0(2) . . ? C3 C4 C24 120.3(2) . . ? C4 C5 C6 122.0(2) . . ? C4 C5 H5 119 . . ? C6 C5 H5 119 . . ? C5 C6 C1 118.8(2) . . ? C5 C6 C7 120.9(2) . . ? C1 C6 C7 120.4(2) . . ? N8 C7 C6 112.45(17) . . ? N8 C7 H7A 109.1 . . ? C6 C7 H7A 109.1 . . ? N8 C7 H7B 109.1 . . ? C6 C7 H7B 109.1 . . ? H7A C7 H7B 107.8 . . ? N8 C9 C10 113.84(18) . . ? N8 C9 H9A 108.8 . . ? C10 C9 H9A 108.8 . . ? N8 C9 H9B 108.8 . . ? C10 C9 H9B 108.8 . . ? H9A C9 H9B 107.7 . . ? C11 C10 C15 119.33(18) . . ? C11 C10 C9 119.49(19) . . ? C15 C10 C9 121.08(18) . . ? C12 C11 C10 121.5(2) . . ? C12 C11 H11 119.3 . . ? C10 C11 H11 119.3 . . ? C13 C12 C11 117.8(2) . . ? C13 C12 C29 121.6(2) . . ? C11 C12 C29 120.6(2) . . ? C12 C13 C14 123.6(2) . . ? C12 C13 H13 118.2 . . ? C14 C13 H13 118.2 . . ? C13 C14 C15 116.6(2) . . ? C13 C14 C25 121.92(19) . . ? C15 C14 C25 121.49(18) . . ? O2 C15 C10 119.58(18) . . ? O2 C15 C14 119.30(19) . . ? C10 C15 C14 121.12(18) . . ? N8 C16 C17 111.75(19) . . ? N8 C16 H16A 109.3 . . ? C17 C16 H16A 109.3 . . ? N8 C16 H16B 109.3 . . ? C17 C16 H16B 109.3 . . ? H16A C16 H16B 107.9 . . ? O18B C17 O18A 24.0(4) . . ? O18B C17 C16 126.4(6) . . ? O18A C17 C16 105.9(3) . . ? O18B C17 H17A 108.3 . . ? O18A C17 H17A 110.5 . . ? C16 C17 H17A 110.5 . . ? O18B C17 H17B 89.7 . . ? O18A C17 H17B 110.5 . . ? C16 C17 H17B 110.5 . . ? H17A C17 H17B 108.7 . . ? C2 C20 C21 110.91(17) . . ? C2 C20 C23 112.12(19) . . ? C21 C20 C23 107.15(19) . . ? C2 C20 C22 109.41(18) . . ? C21 C20 C22 110.13(19) . . ? C23 C20 C22 107.02(18) . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C20 C23 H23A 109.5 . . ? C20 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C20 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C4 C24 H24A 109.5 . . ? C4 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C4 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C28 C25 C26 107.4(2) . . ? C28 C25 C14 111.09(19) . . ? C26 C25 C14 111.98(19) . . ? C28 C25 C27 110.3(2) . . ? C26 C25 C27 107.09(19) . . ? C14 C25 C27 108.86(19) . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C25 C27 H27A 109.5 . . ? C25 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C25 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C25 C28 H28A 109.5 . . ? C25 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C25 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C12 C29 H29A 109.5 . . ? C12 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C12 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C16 N8 C9 113.17(16) . . ? C16 N8 C7 111.07(17) . . ? C9 N8 C7 108.90(17) . . ? C1 O1 H1 110(2) . . ? C15 O2 H2 105.1(17) . . ? C19A O18A C17 109.7(4) . . ? O18A C19A C19B 111.0(5) . 2_655 ? O18A C19A H19A 109.4 . . ? C19B C19A H19A 109.4 2_655 . ? O18A C19A H19B 109.4 . . ? C19B C19A H19B 109.4 2_655 . ? H19A C19A H19B 108 . . ? C17 O18B C19B 106.7(10) . . ? O18B C19B C19A 109.7(12) . 2_655 ? O18B C19B H19C 109.7 . . ? C19A C19B H19C 109.7 2_655 . ? O18B C19B H19D 109.7 . . ? C19A C19B H19D 109.7 2_655 . ? H19C C19B H19D 108.2 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 -179.65(17) . . . . ? C6 C1 C2 C3 -0.6(3) . . . . ? O1 C1 C2 C20 -0.5(3) . . . . ? C6 C1 C2 C20 178.51(19) . . . . ? C1 C2 C3 C4 1.2(3) . . . . ? C20 C2 C3 C4 -177.9(2) . . . . ? C2 C3 C4 C5 -0.9(3) . . . . ? C2 C3 C4 C24 179.9(2) . . . . ? C3 C4 C5 C6 0.0(3) . . . . ? C24 C4 C5 C6 179.2(2) . . . . ? C4 C5 C6 C1 0.5(3) . . . . ? C4 C5 C6 C7 179.7(2) . . . . ? O1 C1 C6 C5 178.78(18) . . . . ? C2 C1 C6 C5 -0.2(3) . . . . ? O1 C1 C6 C7 -0.4(3) . . . . ? C2 C1 C6 C7 -179.38(18) . . . . ? C5 C6 C7 N8 112.3(2) . . . . ? C1 C6 C7 N8 -68.5(3) . . . . ? N8 C9 C10 C11 139.3(2) . . . . ? N8 C9 C10 C15 -44.3(3) . . . . ? C15 C10 C11 C12 -0.3(3) . . . . ? C9 C10 C11 C12 176.2(2) . . . . ? C10 C11 C12 C13 1.8(3) . . . . ? C10 C11 C12 C29 -176.7(2) . . . . ? C11 C12 C13 C14 -1.0(3) . . . . ? C29 C12 C13 C14 177.5(2) . . . . ? C12 C13 C14 C15 -1.3(3) . . . . ? C12 C13 C14 C25 178.4(2) . . . . ? C11 C10 C15 O2 177.94(19) . . . . ? C9 C10 C15 O2 1.6(3) . . . . ? C11 C10 C15 C14 -2.2(3) . . . . ? C9 C10 C15 C14 -178.57(19) . . . . ? C13 C14 C15 O2 -177.25(19) . . . . ? C25 C14 C15 O2 3.0(3) . . . . ? C13 C14 C15 C10 2.9(3) . . . . ? C25 C14 C15 C10 -176.8(2) . . . . ? N8 C16 C17 O18B 44.9(8) . . . . ? N8 C16 C17 O18A 59.0(4) . . . . ? C3 C2 C20 C21 -120.3(2) . . . . ? C1 C2 C20 C21 60.6(3) . . . . ? C3 C2 C20 C23 -0.6(3) . . . . ? C1 C2 C20 C23 -179.68(19) . . . . ? C3 C2 C20 C22 118.0(2) . . . . ? C1 C2 C20 C22 -61.1(3) . . . . ? C13 C14 C25 C28 119.7(2) . . . . ? C15 C14 C25 C28 -60.6(3) . . . . ? C13 C14 C25 C26 -0.4(3) . . . . ? C15 C14 C25 C26 179.3(2) . . . . ? C13 C14 C25 C27 -118.6(2) . . . . ? C15 C14 C25 C27 61.1(3) . . . . ? C17 C16 N8 C9 142.3(2) . . . . ? C17 C16 N8 C7 -94.9(2) . . . . ? C10 C9 N8 C16 -60.2(2) . . . . ? C10 C9 N8 C7 175.72(17) . . . . ? C6 C7 N8 C16 164.06(19) . . . . ? C6 C7 N8 C9 -70.7(2) . . . . ? O18B C17 O18A C19A -28.3(17) . . . . ? C16 C17 O18A C19A -179.4(5) . . . . ? C17 O18A C19A C19B 164.5(7) . . . 2_655 ? O18A C17 O18B C19B 63.4(18) . . . . ? C16 C17 O18B C19B 98.7(11) . . . . ? C17 O18B C19B C19A 175.7(6) . . . 2_655 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 N8 0.86(3) 2.52(3) 3.120(2) 128(3) . O1 H1 O18A 0.86(3) 2.19(4) 3.015(7) 160(3) . O2 H2 N8 0.91(3) 1.90(3) 2.742(2) 152(2) . # END of CIF