# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name _publ_author_address 'Hennrich, Gunther' ;Departmento de Quimica Organica Universidad Autonoma de Madrid Cantoblanco E-28049 Madrid, Spain ; 'Murillo, Teresa' ;Departmento de Quimica Organica Universidad Autonoma de Madrid Cantoblanco E-28049 Madrid, Spain ; 'Pados, Pilar' ;Departmento de Quimica Organica Universidad Autonoma de Madrid Cantoblanco E-28049 Madrid, Spain ; 'Kai, Song' ;Department of Chemistry University of Leuven Celestijnenlaan 200 D B-3001 Leuven, Belgium ; 'Asselberghs, Inge' ;Department of Chemistry University of Leuven Celestijnenlaan 200 D B-3001 Leuven, Belgium ; 'Clays, Koen' ;Department of Chemistry University of Leuven Celestijnenlaan 200 D B-3001 Leuven, Belgium ; 'Persoons, Andre' ;Department of Chemistry University of Leuven Celestijnenlaan 200 D B-3001 Leuven, Belgium ; 'Benet-Buchholz, Jordi' ;Institut Catala d'Investigacio Quimica (ICIQ) X-ray Diffraction Unit Avgda. Paisos Catalans s/n E-43007 Tarragona, Spain ; 'de Mendoza, Javier' ;Institut Catala d'Investigacio Quimica (ICIQ) Avgda. Paisos Catalans s/n E-43007 Tarragona, Spain ; _publ_contact_author_name 'Dr Gunther Hennrich' _publ_contact_author_address ; Quimica Organica Universidad Autonoma de Madrid Cantoblanco Madrid 28049 SPAIN ; _publ_contact_author_email GUNTHER.HENNRICH@UAM.ES _publ_requested_journal 'Chemical Communications' _publ_section_title ; Tetraalkynyl calix[4]arenes with advanced NLO properties ; data_gh113_0m _database_code_depnum_ccdc_archive 'CCDC 264208' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C89.50 H80 N4 O12' _chemical_formula_weight 1403.58 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 29.410(3) _cell_length_b 17.1574(19) _cell_length_c 31.210(4) _cell_angle_alpha 90.00 _cell_angle_beta 108.879(3) _cell_angle_gamma 90.00 _cell_volume 14902(3) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9640 _cell_measurement_theta_min 2.68 _cell_measurement_theta_max 31.14 _exptl_crystal_preparation ; Slow evaporation of toluene at room temperature ; _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.251 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 5928 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.839070 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details ; SADABS Version 2.1 2003 Bruker-Nonius Blessing, Acta Cryst. (1995) A51 33-38 ; _exptl_special_details ; It should be noted that the esd's of the cell dimensions are probably too low; they should be multiplied by a factor of 2 to 10 ; _diffrn_ambient_temperature 100(2) _diffrn_measurement_specimen_suppport 'magnetic support whith 10 micron nylon fiber cryoloop' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'rotating anode X-ray tube' _diffrn_source_type 'Bruker-Nonius FR 591' _diffrn_source_power 50 _diffrn_source_current 90 _diffrn_source_size '3 mm x 0.3 mm fine focus' _diffrn_radiation_monochromator 'Multilayer Montel 200 mirrors' _diffrn_detector_type '4K CCD area detector APEX II' _diffrn_measurement_device_type 'Kappa 4-axis goniometer bruker-nonius' _diffrn_measurement_method ; Fullsphere data collection, phi and omega scans ; _diffrn_detector_area_resol_mean 512 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 70045 _diffrn_reflns_av_R_equivalents 0.1017 _diffrn_reflns_av_sigmaI/netI 0.0896 _diffrn_reflns_limit_h_min -37 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_theta_min 2.68 _diffrn_reflns_theta_max 27.00 _reflns_number_total 15670 _reflns_number_gt 8665 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker-Nonius Apex v1.0-22 2002' _computing_cell_refinement 'Bruker-Nonius Apex v1.0-22 2002' _computing_data_reduction 'SAINT+ Version 7.06A Bruker-Nonius, 2004' _computing_structure_solution 'Shelxtl Version 6.12 (Sheldrick, 2001)' _computing_structure_refinement 'Shelxtl Version 6.12 (Sheldrick, 2001)' _computing_molecular_graphics 'Shelxtl Version 6.12 (Sheldrick, 2001)' _computing_publication_material 'Shelxtl Version 6.12 (Sheldrick, 2001)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. One of the toluene molecules is refined with an occupancy of 0.5 and is disordered in two positions. ; _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^)+(0.1433P)^2^+35.8381P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 15670 _refine_ls_number_parameters 977 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1553 _refine_ls_R_factor_gt 0.0879 _refine_ls_wR_factor_ref 0.2899 _refine_ls_wR_factor_gt 0.2188 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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 0.04123(10) 0.91823(15) 0.17031(9) 0.0350(6) Uani 1 1 d . . . C1 C 0.04712(14) 0.8421(2) 0.15847(12) 0.0316(8) Uani 1 1 d . . . N1 N 0.04234(14) 0.2340(2) 0.04484(13) 0.0457(9) Uani 1 1 d . . . O2 O 0.04000(13) 0.22437(18) 0.00501(11) 0.0547(9) Uani 1 1 d . . . C2 C 0.05744(14) 0.7840(2) 0.19192(12) 0.0321(8) Uani 1 1 d . . . N2 N 0.09588(15) 0.6955(2) -0.25576(12) 0.0471(10) Uani 1 1 d . . . C3 C 0.06040(15) 0.7076(2) 0.17917(13) 0.0349(9) Uani 1 1 d . . . H3A H 0.0666 0.6676 0.2013 0.042 Uiso 1 1 calc R . . O3 O 0.04025(14) 0.18071(18) 0.07038(12) 0.0611(10) Uani 1 1 d . . . N3 N 0.2077(2) 0.2436(2) 0.06542(13) 0.0693(16) Uani 1 1 d . . . O4 O 0.13424(10) 0.92863(14) 0.13084(8) 0.0315(6) Uani 1 1 d . . . C4 C 0.05445(14) 0.6883(2) 0.13406(12) 0.0332(9) Uani 1 1 d . . . N4 N 0.24484(14) 0.35748(18) 0.52682(11) 0.0370(8) Uani 1 1 d . . . O5 O 0.13124(13) 0.7001(2) -0.26691(10) 0.0512(8) Uani 1 1 d . . . C5 C 0.04660(15) 0.7477(2) 0.10177(13) 0.0348(9) Uani 1 1 d . . . H5A H 0.0437 0.7349 0.0714 0.042 Uiso 1 1 calc R . . C6 C 0.04299(14) 0.8247(2) 0.11337(12) 0.0311(8) Uani 1 1 d . . . O6 O 0.05647(15) 0.6799(3) -0.28183(13) 0.0984(17) Uani 1 1 d . . . O7 O 0.24113(9) 0.92600(12) 0.20406(8) 0.0275(6) Uani 1 1 d . . . C7 C -0.00787(17) 0.9350(3) 0.16540(15) 0.0451(11) Uani 1 1 d . . . H7A H -0.0195 0.8991 0.1844 0.054 Uiso 1 1 calc R . . H7B H -0.0282 0.9280 0.1335 0.054 Uiso 1 1 calc R . . C8 C -0.01093(19) 1.0181(3) 0.1799(2) 0.0622(15) Uani 1 1 d . . . H8A H -0.0438 1.0279 0.1808 0.075 Uiso 1 1 calc R . . H8B H 0.0117 1.0252 0.2109 0.075 Uiso 1 1 calc R . . O8 O 0.2357(2) 0.2265(2) 0.04546(18) 0.0995(18) Uani 1 1 d . . . C9 C 0.0003(2) 1.0766(3) 0.1494(3) 0.084(2) Uani 1 1 d . . . H9A H -0.0024 1.1292 0.1606 0.127 Uiso 1 1 calc R . . H9B H -0.0225 1.0709 0.1187 0.127 Uiso 1 1 calc R . . H9C H 0.0330 1.0682 0.1489 0.127 Uiso 1 1 calc R . . O9 O 0.1774(3) 0.2017(2) 0.06952(16) 0.128(3) Uani 1 1 d . . . O10 O 0.15069(10) 0.87652(13) 0.23667(8) 0.0310(6) Uani 1 1 d . . . C10 C 0.05633(15) 0.6087(2) 0.12062(12) 0.0372(9) Uani 1 1 d . . . C11 C 0.05645(15) 0.5433(2) 0.10904(12) 0.0369(9) Uani 1 1 d . . . O11 O 0.27866(12) 0.37586(17) 0.55964(11) 0.0510(8) Uani 1 1 d . . . C12 C 0.05441(15) 0.4641(2) 0.09354(13) 0.0347(9) Uani 1 1 d . . . O12 O 0.22241(13) 0.29673(16) 0.52382(11) 0.0530(9) Uani 1 1 d . . . C13 C 0.05832(16) 0.4013(2) 0.12320(13) 0.0394(10) Uani 1 1 d . . . H13A H 0.0637 0.4110 0.1544 0.047 Uiso 1 1 calc R . . C14 C 0.05453(16) 0.3262(2) 0.10795(13) 0.0389(10) Uani 1 1 d . . . H14A H 0.0569 0.2838 0.1281 0.047 Uiso 1 1 calc R . . C15 C 0.04719(15) 0.3132(2) 0.06231(13) 0.0366(9) Uani 1 1 d . . . C16 C 0.04306(15) 0.3738(2) 0.03194(13) 0.0348(9) Uani 1 1 d . . . H16A H 0.0376 0.3635 0.0008 0.042 Uiso 1 1 calc R . . C17 C 0.04699(15) 0.4494(2) 0.04778(13) 0.0354(9) Uani 1 1 d . . . H17A H 0.0446 0.4916 0.0275 0.042 Uiso 1 1 calc R . . C18 C 0.03810(15) 0.8877(2) 0.07786(12) 0.0350(9) Uani 1 1 d . . . H18A H 0.0076 0.8807 0.0527 0.042 Uiso 1 1 calc R . . H18B H 0.0375 0.9397 0.0915 0.042 Uiso 1 1 calc R . . C19 C 0.12648(14) 0.89955(18) 0.08782(11) 0.0269(8) Uani 1 1 d . . . C20 C 0.07962(14) 0.88309(19) 0.06004(11) 0.0293(8) Uani 1 1 d . . . C21 C 0.07391(15) 0.8534(2) 0.01647(11) 0.0308(9) Uani 1 1 d . . . H21A H 0.0425 0.8438 -0.0038 0.037 Uiso 1 1 calc R . . C22 C 0.11327(14) 0.83817(19) 0.00271(11) 0.0286(8) Uani 1 1 d . . . C23 C 0.15928(14) 0.85076(18) 0.03251(11) 0.0260(8) Uani 1 1 d . . . H23A H 0.1862 0.8383 0.0233 0.031 Uiso 1 1 calc R . . C24 C 0.16668(14) 0.88144(18) 0.07576(11) 0.0260(8) Uani 1 1 d . . . C25 C 0.12109(16) 1.0078(2) 0.13433(14) 0.0416(10) Uani 1 1 d . . . H25A H 0.1054 1.0116 0.1580 0.050 Uiso 1 1 calc R . . H25B H 0.0972 1.0237 0.1052 0.050 Uiso 1 1 calc R . . C26 C 0.16142(18) 1.0621(2) 0.14536(17) 0.0492(12) Uani 1 1 d . . . H26A H 0.1728 1.0672 0.1189 0.059 Uiso 1 1 calc R . . H26B H 0.1882 1.0409 0.1709 0.059 Uiso 1 1 calc R . . C27 C 0.14765(18) 1.1432(2) 0.15835(16) 0.0494(12) Uani 1 1 d . . . H27A H 0.1753 1.1783 0.1643 0.074 Uiso 1 1 calc R . . H27B H 0.1382 1.1388 0.1856 0.074 Uiso 1 1 calc R . . H27C H 0.1207 1.1639 0.1334 0.074 Uiso 1 1 calc R . . C28 C 0.10797(15) 0.80770(19) -0.04159(12) 0.0313(9) Uani 1 1 d . . . C29 C 0.10684(16) 0.7829(2) -0.07805(12) 0.0339(9) Uani 1 1 d . . . C30 C 0.10533(15) 0.7558(2) -0.12222(11) 0.0314(9) Uani 1 1 d . . . C31 C 0.14568(15) 0.7587(2) -0.13546(12) 0.0325(9) Uani 1 1 d . . . H31A H 0.1754 0.7755 -0.1146 0.039 Uiso 1 1 calc R . . C32 C 0.14338(15) 0.7372(2) -0.17920(12) 0.0314(9) Uani 1 1 d . . . H32A H 0.1710 0.7394 -0.1887 0.038 Uiso 1 1 calc R . . C33 C 0.09963(16) 0.7126(2) -0.20811(12) 0.0380(10) Uani 1 1 d . . . C34 C 0.05999(17) 0.7049(3) -0.19508(14) 0.0519(13) Uani 1 1 d . . . H34A H 0.0310 0.6848 -0.2156 0.062 Uiso 1 1 calc R . . C35 C 0.06226(17) 0.7266(3) -0.15172(14) 0.0458(11) Uani 1 1 d . . . H35A H 0.0348 0.7216 -0.1421 0.055 Uiso 1 1 calc R . . C36 C 0.21634(14) 0.89019(19) 0.10902(11) 0.0275(8) Uani 1 1 d . . . H36A H 0.2199 0.9427 0.1228 0.033 Uiso 1 1 calc R . . H36B H 0.2403 0.8851 0.0930 0.033 Uiso 1 1 calc R . . C37 C 0.23597(13) 0.84801(18) 0.19142(11) 0.0237(7) Uani 1 1 d . . . C38 C 0.22593(13) 0.82888(18) 0.14586(11) 0.0243(7) Uani 1 1 d . . . C39 C 0.22267(13) 0.75052(19) 0.13399(11) 0.0256(8) Uani 1 1 d . . . H39A H 0.2160 0.7362 0.1032 0.031 Uiso 1 1 calc R . . C40 C 0.22902(14) 0.69251(19) 0.16682(12) 0.0280(8) Uani 1 1 d . . . C41 C 0.23725(14) 0.71409(19) 0.21197(11) 0.0282(8) Uani 1 1 d . . . H41A H 0.2408 0.6748 0.2343 0.034 Uiso 1 1 calc R . . C42 C 0.24022(13) 0.79165(19) 0.22465(11) 0.0245(7) Uani 1 1 d . . . C43 C 0.29011(14) 0.9494(2) 0.22162(13) 0.0327(9) Uani 1 1 d . . . H43A H 0.3044 0.9515 0.1969 0.039 Uiso 1 1 calc R . . H43B H 0.3086 0.9113 0.2445 0.039 Uiso 1 1 calc R . . C44 C 0.29232(17) 1.0288(2) 0.24299(14) 0.0409(10) Uani 1 1 d . . . H44A H 0.2766 1.0672 0.2191 0.049 Uiso 1 1 calc R . . H44B H 0.2741 1.0274 0.2647 0.049 Uiso 1 1 calc R . . C45 C 0.34295(19) 1.0554(3) 0.26748(17) 0.0561(14) Uani 1 1 d . . . H45A H 0.3424 1.1092 0.2779 0.084 Uiso 1 1 calc R . . H45B H 0.3620 1.0529 0.2469 0.084 Uiso 1 1 calc R . . H45C H 0.3574 1.0215 0.2936 0.084 Uiso 1 1 calc R . . C46 C 0.22611(14) 0.6120(2) 0.15342(12) 0.0311(8) Uani 1 1 d . . . C47 C 0.22331(15) 0.5466(2) 0.14092(12) 0.0324(9) Uani 1 1 d . . . C48 C 0.22002(15) 0.4684(2) 0.12310(12) 0.0323(9) Uani 1 1 d . . . C49 C 0.25024(17) 0.4453(2) 0.09962(15) 0.0415(10) Uani 1 1 d . . . H49A H 0.2740 0.4802 0.0965 0.050 Uiso 1 1 calc R . . C50 C 0.24629(18) 0.3719(2) 0.08056(15) 0.0470(11) Uani 1 1 d . . . H50A H 0.2669 0.3561 0.0641 0.056 Uiso 1 1 calc R . . C51 C 0.21220(19) 0.3229(2) 0.08591(13) 0.0448(12) Uani 1 1 d . . . C52 C 0.18150(19) 0.3428(2) 0.10925(14) 0.0474(12) Uani 1 1 d . . . H52A H 0.1582 0.3068 0.1123 0.057 Uiso 1 1 calc R . . C53 C 0.18535(17) 0.4169(2) 0.12836(13) 0.0397(10) Uani 1 1 d . . . H53A H 0.1647 0.4322 0.1448 0.048 Uiso 1 1 calc R . . C54 C 0.24563(14) 0.81369(19) 0.27342(11) 0.0272(8) Uani 1 1 d . . . H54A H 0.2757 0.7909 0.2941 0.033 Uiso 1 1 calc R . . H54B H 0.2477 0.8711 0.2768 0.033 Uiso 1 1 calc R . . C55 C 0.15724(15) 0.81290(19) 0.26534(11) 0.0285(8) Uani 1 1 d . . . C56 C 0.20346(14) 0.78423(19) 0.28592(11) 0.0282(8) Uani 1 1 d . . . C57 C 0.20835(15) 0.72138(19) 0.31589(11) 0.0311(9) Uani 1 1 d . . . H57A H 0.2395 0.7014 0.3313 0.037 Uiso 1 1 calc R . . C58 C 0.16903(16) 0.6881(2) 0.32334(12) 0.0334(9) Uani 1 1 d . . . C59 C 0.12329(15) 0.7143(2) 0.29949(12) 0.0331(9) Uani 1 1 d . . . H59A H 0.0961 0.6890 0.3033 0.040 Uiso 1 1 calc R . . C60 C 0.11659(15) 0.7774(2) 0.26996(11) 0.0321(9) Uani 1 1 d . . . C61 C 0.16506(16) 0.9503(2) 0.25902(13) 0.0366(9) Uani 1 1 d . . . H61A H 0.1787 0.9834 0.2402 0.044 Uiso 1 1 calc R . . H61B H 0.1906 0.9414 0.2883 0.044 Uiso 1 1 calc R . . C62 C 0.12431(16) 0.9924(2) 0.26727(14) 0.0381(10) Uani 1 1 d . . . H62A H 0.1126 0.9618 0.2884 0.046 Uiso 1 1 calc R . . H62B H 0.0976 0.9975 0.2384 0.046 Uiso 1 1 calc R . . C63 C 0.13937(18) 1.0732(2) 0.28708(16) 0.0453(11) Uani 1 1 d . . . H63A H 0.1121 1.0988 0.2927 0.068 Uiso 1 1 calc R . . H63B H 0.1498 1.1044 0.2656 0.068 Uiso 1 1 calc R . . H63C H 0.1659 1.0684 0.3156 0.068 Uiso 1 1 calc R . . C64 C 0.17682(16) 0.6233(2) 0.35505(13) 0.0364(9) Uani 1 1 d . . . C65 C 0.18631(16) 0.5727(2) 0.38188(13) 0.0367(9) Uani 1 1 d . . . C66 C 0.20101(15) 0.5157(2) 0.41796(12) 0.0326(9) Uani 1 1 d . . . C67 C 0.24145(15) 0.5313(2) 0.45484(13) 0.0340(9) Uani 1 1 d . . . H67A H 0.2590 0.5780 0.4556 0.041 Uiso 1 1 calc R . . C68 C 0.25634(15) 0.4790(2) 0.49062(13) 0.0337(9) Uani 1 1 d . . . H68A H 0.2840 0.4894 0.5160 0.040 Uiso 1 1 calc R . . C69 C 0.23025(15) 0.4119(2) 0.48850(12) 0.0308(8) Uani 1 1 d . . . C70 C 0.19031(15) 0.3936(2) 0.45178(13) 0.0346(9) Uani 1 1 d . . . H70A H 0.1734 0.3462 0.4510 0.042 Uiso 1 1 calc R . . C71 C 0.17567(16) 0.4460(2) 0.41621(13) 0.0352(9) Uani 1 1 d . . . H71A H 0.1485 0.4347 0.3906 0.042 Uiso 1 1 calc R . . C72 C 0.06670(15) 0.8038(2) 0.24164(12) 0.0338(9) Uani 1 1 d . . . H72A H 0.0637 0.8608 0.2450 0.041 Uiso 1 1 calc R . . H72B H 0.0424 0.7777 0.2524 0.041 Uiso 1 1 calc R . . C1LA C 0.38599(16) 0.4200(2) 0.03955(14) 0.0414(10) Uani 1 1 d . . . C2LA C 0.38492(19) 0.3426(2) 0.05222(15) 0.0484(12) Uani 1 1 d . . . H2LB H 0.3898 0.3026 0.0331 0.058 Uiso 1 1 calc R . . C3LA C 0.3769(2) 0.3228(3) 0.09166(16) 0.0534(13) Uani 1 1 d . . . H3LB H 0.3769 0.2695 0.0998 0.064 Uiso 1 1 calc R . . C4LA C 0.36889(18) 0.3798(3) 0.11995(16) 0.0479(11) Uani 1 1 d . . . H4LB H 0.3627 0.3661 0.1470 0.057 Uiso 1 1 calc R . . C5LA C 0.37010(17) 0.4571(2) 0.10780(15) 0.0457(11) Uani 1 1 d . . . H5LB H 0.3650 0.4969 0.1269 0.055 Uiso 1 1 calc R . . C6LA C 0.37859(16) 0.4771(2) 0.06825(14) 0.0408(10) Uani 1 1 d . . . H6LB H 0.3794 0.5305 0.0605 0.049 Uiso 1 1 calc R . . C7LA C 0.3945(2) 0.4419(3) -0.00372(15) 0.0550(13) Uani 1 1 d . . . H7LD H 0.3762 0.4890 -0.0162 0.082 Uiso 1 1 calc R . . H7LE H 0.3840 0.3992 -0.0256 0.082 Uiso 1 1 calc R . . H7LF H 0.4288 0.4517 0.0023 0.082 Uiso 1 1 calc R . . C1LB C 0.39451(19) 1.0358(2) 0.03162(16) 0.0479(11) Uani 1 1 d . . . C2LB C 0.36305(17) 1.0131(2) -0.00978(15) 0.0430(10) Uani 1 1 d . . . H2LA H 0.3398 1.0492 -0.0271 0.052 Uiso 1 1 calc R . . C3LB C 0.36465(17) 0.9392(2) -0.02659(14) 0.0429(10) Uani 1 1 d . . . H3LA H 0.3432 0.9252 -0.0555 0.051 Uiso 1 1 calc R . . C4LB C 0.39731(18) 0.8861(2) -0.00151(16) 0.0471(11) Uani 1 1 d . . . H4LA H 0.3985 0.8348 -0.0127 0.056 Uiso 1 1 calc R . . C5LB C 0.42850(17) 0.9080(3) 0.04021(17) 0.0504(12) Uani 1 1 d . . . H5LA H 0.4509 0.8713 0.0580 0.060 Uiso 1 1 calc R . . C6LB C 0.42756(17) 0.9816(3) 0.05613(15) 0.0482(11) Uani 1 1 d . . . H6LA H 0.4500 0.9960 0.0845 0.058 Uiso 1 1 calc R . . C7LB C 0.3933(3) 1.1160(3) 0.0505(2) 0.0745(18) Uani 1 1 d . . . H7LA H 0.3826 1.1536 0.0256 0.112 Uiso 1 1 calc R . . H7LB H 0.4256 1.1302 0.0703 0.112 Uiso 1 1 calc R . . H7LC H 0.3710 1.1167 0.0679 0.112 Uiso 1 1 calc R . . C1LC C 0.5026(2) 1.0189(6) 0.2697(2) 0.055(3) Uani 0.50 1 d PG A -1 C2LC C 0.5203(2) 1.0393(7) 0.2350(3) 0.111(8) Uani 0.50 1 d PG A -1 H2LC H 0.5530 1.0540 0.2418 0.133 Uiso 0.50 1 calc PR A -1 C3LC C 0.4901(3) 1.0382(8) 0.1903(3) 0.105(8) Uani 0.50 1 d PG A -1 H3LC H 0.5022 1.0521 0.1665 0.127 Uiso 0.50 1 calc PR A -1 C4LC C 0.4422(3) 1.0167(7) 0.18033(19) 0.052(3) Uani 0.50 1 d PG A -1 H4LC H 0.4216 1.0159 0.1498 0.063 Uiso 0.50 1 calc PR A -1 C5LC C 0.4246(2) 0.9963(6) 0.2151(3) 0.076(3) Uani 0.50 1 d PG A -1 H5LC H 0.3918 0.9816 0.2083 0.091 Uiso 0.50 1 calc PR A -1 C6LC C 0.4548(3) 0.9973(6) 0.2597(2) 0.072(4) Uani 0.50 1 d PG A -1 H6LC H 0.4427 0.9834 0.2835 0.086 Uiso 0.50 1 calc PR A -1 C7LC C 0.5331(7) 1.0214(11) 0.3170(5) 0.071(5) Uani 0.50 1 d P A -1 H7LG H 0.5208 0.9847 0.3347 0.107 Uiso 0.50 1 calc PR A -1 H7LH H 0.5329 1.0742 0.3289 0.107 Uiso 0.50 1 calc PR A -1 H7LI H 0.5660 1.0069 0.3193 0.107 Uiso 0.50 1 calc PR A -1 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 0.0435(16) 0.0371(14) 0.0238(13) -0.0039(11) 0.0100(12) 0.0064(12) C1 0.034(2) 0.038(2) 0.0213(17) -0.0031(14) 0.0059(16) 0.0007(16) N1 0.055(2) 0.0338(18) 0.039(2) 0.0041(15) 0.0036(18) -0.0056(16) O2 0.079(2) 0.0429(17) 0.0385(17) -0.0090(14) 0.0138(17) -0.0047(15) C2 0.033(2) 0.041(2) 0.0221(17) -0.0019(15) 0.0092(16) 0.0015(16) N2 0.050(2) 0.065(2) 0.0205(17) -0.0122(16) 0.0036(18) 0.0145(19) C3 0.041(2) 0.040(2) 0.0220(17) 0.0006(15) 0.0080(17) -0.0012(17) O3 0.085(3) 0.0372(17) 0.0457(18) 0.0082(14) -0.0006(18) -0.0134(16) N3 0.137(5) 0.027(2) 0.0291(19) -0.0047(16) 0.006(3) -0.005(3) O4 0.0500(16) 0.0291(13) 0.0135(11) -0.0045(9) 0.0077(11) 0.0030(11) C4 0.035(2) 0.039(2) 0.0216(17) -0.0039(15) 0.0036(16) -0.0015(16) N4 0.059(2) 0.0240(16) 0.0317(18) 0.0081(13) 0.0198(18) 0.0027(15) O5 0.061(2) 0.069(2) 0.0244(14) -0.0036(14) 0.0153(16) 0.0181(16) C5 0.043(2) 0.040(2) 0.0211(17) -0.0041(15) 0.0099(17) -0.0030(17) C6 0.032(2) 0.042(2) 0.0188(16) -0.0014(14) 0.0071(16) 0.0000(16) O6 0.065(3) 0.191(5) 0.0319(19) -0.050(3) 0.006(2) -0.008(3) O7 0.0460(16) 0.0161(11) 0.0190(11) -0.0023(9) 0.0084(11) -0.0010(10) C7 0.047(3) 0.056(3) 0.032(2) -0.0024(19) 0.012(2) 0.008(2) C8 0.050(3) 0.071(3) 0.062(3) -0.021(3) 0.014(3) 0.016(2) O8 0.163(5) 0.040(2) 0.089(3) -0.028(2) 0.032(3) 0.018(2) C9 0.075(4) 0.045(3) 0.136(7) 0.004(3) 0.038(4) 0.015(3) O9 0.279(8) 0.045(2) 0.070(3) -0.028(2) 0.070(4) -0.076(4) O10 0.0509(16) 0.0213(12) 0.0176(11) 0.0039(9) 0.0066(12) 0.0032(11) C10 0.048(2) 0.040(2) 0.0190(17) 0.0018(15) 0.0041(17) -0.0051(18) C11 0.043(2) 0.048(2) 0.0174(17) 0.0008(16) 0.0072(17) 0.0006(18) O11 0.064(2) 0.0438(17) 0.0367(17) 0.0159(13) 0.0040(16) 0.0017(15) C12 0.042(2) 0.036(2) 0.0226(18) 0.0010(15) 0.0068(17) -0.0030(17) O12 0.093(3) 0.0259(14) 0.0430(17) 0.0093(12) 0.0267(18) -0.0080(15) C13 0.053(3) 0.045(2) 0.0165(16) 0.0024(15) 0.0073(18) -0.0042(19) C14 0.048(3) 0.039(2) 0.0245(18) 0.0090(16) 0.0059(18) -0.0026(18) C15 0.044(2) 0.0320(19) 0.0289(19) -0.0012(15) 0.0049(18) -0.0054(16) C16 0.043(2) 0.037(2) 0.0234(18) 0.0005(15) 0.0093(17) -0.0070(17) C17 0.048(2) 0.035(2) 0.0227(18) 0.0049(15) 0.0105(18) -0.0014(17) C18 0.041(2) 0.038(2) 0.0191(17) -0.0029(15) 0.0004(17) 0.0038(17) C19 0.050(2) 0.0192(15) 0.0109(14) 0.0024(12) 0.0085(16) 0.0014(14) C20 0.045(2) 0.0238(17) 0.0161(15) 0.0019(13) 0.0057(16) 0.0045(15) C21 0.045(2) 0.0281(18) 0.0151(15) -0.0003(13) 0.0041(16) 0.0021(15) C22 0.050(2) 0.0201(16) 0.0133(15) 0.0018(12) 0.0064(16) -0.0003(15) C23 0.045(2) 0.0202(16) 0.0166(15) 0.0019(12) 0.0147(16) 0.0027(14) C24 0.046(2) 0.0184(15) 0.0131(14) 0.0023(12) 0.0090(15) -0.0005(14) C25 0.056(3) 0.034(2) 0.0282(19) -0.0081(16) 0.0037(19) 0.0088(18) C26 0.062(3) 0.033(2) 0.044(2) 0.0048(18) 0.005(2) 0.003(2) C27 0.066(3) 0.028(2) 0.047(3) 0.0005(18) 0.009(2) -0.0008(19) C28 0.052(2) 0.0210(16) 0.0203(17) 0.0015(13) 0.0110(17) 0.0040(15) C29 0.055(3) 0.0223(17) 0.0211(17) 0.0015(13) 0.0074(18) 0.0029(16) C30 0.051(2) 0.0242(17) 0.0143(15) -0.0016(13) 0.0037(17) 0.0050(15) C31 0.049(2) 0.0267(18) 0.0172(16) -0.0012(13) 0.0041(17) 0.0006(16) C32 0.045(2) 0.0275(18) 0.0207(17) 0.0029(13) 0.0089(17) 0.0083(15) C33 0.050(3) 0.043(2) 0.0169(17) -0.0059(15) 0.0043(18) 0.0109(18) C34 0.044(3) 0.081(3) 0.024(2) -0.020(2) 0.002(2) 0.001(2) C35 0.046(3) 0.065(3) 0.0241(19) -0.0084(19) 0.0078(19) 0.006(2) C36 0.042(2) 0.0219(16) 0.0197(16) 0.0021(13) 0.0117(16) -0.0001(14) C37 0.034(2) 0.0167(15) 0.0187(15) -0.0016(12) 0.0060(15) 0.0016(13) C38 0.035(2) 0.0195(15) 0.0173(15) 0.0016(12) 0.0070(15) 0.0026(13) C39 0.038(2) 0.0226(16) 0.0153(15) -0.0031(12) 0.0065(15) 0.0003(14) C40 0.040(2) 0.0221(16) 0.0204(16) -0.0013(13) 0.0078(16) 0.0013(14) C41 0.045(2) 0.0218(16) 0.0163(15) 0.0027(12) 0.0074(16) 0.0012(15) C42 0.036(2) 0.0226(16) 0.0136(14) 0.0029(12) 0.0065(14) 0.0006(14) C43 0.044(2) 0.0258(18) 0.0258(18) -0.0004(14) 0.0077(17) -0.0029(16) C44 0.061(3) 0.0244(18) 0.030(2) -0.0016(15) 0.004(2) -0.0047(17) C45 0.074(3) 0.034(2) 0.043(3) 0.0047(19) -0.005(2) -0.011(2) C46 0.045(2) 0.0290(19) 0.0168(16) 0.0047(13) 0.0067(16) 0.0035(16) C47 0.048(2) 0.0265(18) 0.0191(16) 0.0023(14) 0.0052(17) 0.0028(16) C48 0.047(2) 0.0224(17) 0.0210(17) 0.0006(13) 0.0023(17) 0.0024(15) C49 0.053(3) 0.0269(19) 0.041(2) -0.0072(16) 0.010(2) 0.0009(17) C50 0.068(3) 0.032(2) 0.037(2) -0.0071(17) 0.011(2) 0.010(2) C51 0.079(3) 0.0181(17) 0.0253(19) -0.0002(14) 0.000(2) -0.0008(19) C52 0.076(3) 0.029(2) 0.0242(19) 0.0046(16) -0.002(2) -0.014(2) C53 0.059(3) 0.0303(19) 0.0217(18) 0.0043(15) 0.0021(19) -0.0017(18) C54 0.041(2) 0.0224(16) 0.0135(15) -0.0007(12) 0.0019(15) 0.0012(14) C55 0.051(2) 0.0244(17) 0.0110(14) -0.0028(12) 0.0107(16) 0.0023(15) C56 0.048(2) 0.0207(16) 0.0133(14) -0.0031(12) 0.0067(16) -0.0004(15) C57 0.054(2) 0.0223(17) 0.0144(15) -0.0004(12) 0.0074(17) 0.0022(16) C58 0.057(3) 0.0282(18) 0.0148(15) -0.0005(13) 0.0117(18) 0.0009(17) C59 0.050(2) 0.0332(19) 0.0181(16) -0.0025(14) 0.0142(17) -0.0054(17) C60 0.053(3) 0.0285(18) 0.0147(15) -0.0028(13) 0.0113(17) -0.0002(16) C61 0.057(3) 0.0216(17) 0.0287(19) -0.0003(14) 0.0107(19) 0.0030(16) C62 0.056(3) 0.0277(19) 0.0293(19) -0.0004(15) 0.0123(19) 0.0004(17) C63 0.067(3) 0.028(2) 0.045(2) -0.0039(17) 0.024(2) -0.0010(19) C64 0.053(3) 0.0314(19) 0.0249(18) -0.0023(15) 0.0135(19) -0.0034(17) C65 0.055(3) 0.0313(19) 0.0256(18) 0.0007(15) 0.0158(19) -0.0017(17) C66 0.050(2) 0.0270(18) 0.0248(18) 0.0048(14) 0.0169(18) 0.0015(16) C67 0.057(3) 0.0206(17) 0.0276(18) 0.0033(14) 0.0175(19) -0.0031(16) C68 0.048(2) 0.0265(18) 0.0268(18) 0.0008(14) 0.0126(18) -0.0004(16) C69 0.052(2) 0.0215(16) 0.0235(17) 0.0051(13) 0.0189(18) 0.0039(15) C70 0.053(3) 0.0237(17) 0.0309(19) 0.0006(14) 0.0182(19) -0.0045(16) C71 0.051(3) 0.0316(19) 0.0229(17) 0.0005(14) 0.0112(18) -0.0034(17) C72 0.043(2) 0.039(2) 0.0216(17) -0.0020(15) 0.0136(17) 0.0026(17) C1LA 0.055(3) 0.032(2) 0.034(2) 0.0063(16) 0.009(2) 0.0026(18) C2LA 0.079(3) 0.030(2) 0.039(2) -0.0011(17) 0.022(2) 0.004(2) C3LA 0.086(4) 0.031(2) 0.046(3) 0.0080(19) 0.025(3) 0.003(2) C4LA 0.064(3) 0.044(2) 0.036(2) 0.0076(18) 0.017(2) 0.002(2) C5LA 0.058(3) 0.038(2) 0.035(2) -0.0012(17) 0.008(2) 0.0063(19) C6LA 0.051(3) 0.031(2) 0.033(2) 0.0034(16) 0.004(2) 0.0044(17) C7LA 0.094(4) 0.036(2) 0.036(2) 0.0090(18) 0.022(3) 0.008(2) C1LB 0.071(3) 0.036(2) 0.044(2) -0.0039(19) 0.028(2) -0.011(2) C2LB 0.052(3) 0.039(2) 0.038(2) 0.0139(18) 0.014(2) 0.0035(19) C3LB 0.054(3) 0.044(2) 0.028(2) 0.0018(17) 0.009(2) -0.0069(19) C4LB 0.067(3) 0.033(2) 0.044(2) 0.0024(18) 0.023(2) -0.001(2) C5LB 0.048(3) 0.056(3) 0.045(3) 0.017(2) 0.012(2) 0.007(2) C6LB 0.051(3) 0.062(3) 0.029(2) 0.000(2) 0.009(2) -0.009(2) C7LB 0.120(5) 0.045(3) 0.087(4) -0.022(3) 0.073(4) -0.022(3) C1LC 0.069(8) 0.066(7) 0.031(5) 0.004(4) 0.018(6) 0.003(6) C2LC 0.078(13) 0.20(2) 0.047(8) 0.016(11) 0.013(8) -0.071(13) C3LC 0.065(12) 0.20(2) 0.058(10) -0.008(10) 0.028(9) -0.062(11) C4LC 0.045(8) 0.069(7) 0.038(6) -0.012(5) 0.006(6) -0.011(6) C5LC 0.075(8) 0.100(9) 0.050(6) -0.012(6) 0.015(6) -0.017(7) C6LC 0.098(11) 0.068(7) 0.052(7) 0.015(6) 0.028(7) -0.017(7) C7LC 0.066(14) 0.100(11) 0.043(7) 0.002(6) 0.010(8) 0.013(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.384(4) . ? O1 C7 1.431(5) . ? C1 C2 1.403(5) . ? C1 C6 1.405(5) . ? N1 O3 1.227(5) . ? N1 O2 1.234(5) . ? N1 C15 1.454(5) . ? C2 C3 1.381(5) . ? C2 C72 1.524(5) . ? N2 O5 1.201(5) . ? N2 O6 1.211(5) . ? N2 C33 1.485(5) . ? C3 C4 1.401(5) . ? N3 O9 1.183(8) . ? N3 O8 1.218(8) . ? N3 C51 1.491(5) . ? O4 C19 1.381(4) . ? O4 C25 1.426(4) . ? C4 C5 1.398(5) . ? C4 C10 1.436(6) . ? N4 O11 1.216(4) . ? N4 O12 1.221(4) . ? N4 C69 1.468(5) . ? C5 C6 1.383(5) . ? C6 C18 1.522(5) . ? O7 C37 1.389(4) . ? O7 C43 1.423(5) . ? C7 C8 1.506(7) . ? C8 C9 1.491(9) . ? O10 C55 1.385(4) . ? O10 C61 1.441(4) . ? C10 C11 1.179(6) . ? C11 C12 1.436(6) . ? C12 C17 1.396(5) . ? C12 C13 1.402(5) . ? C13 C14 1.365(6) . ? C14 C15 1.388(6) . ? C15 C16 1.386(5) . ? C16 C17 1.379(5) . ? C18 C20 1.499(6) . ? C19 C24 1.387(6) . ? C19 C20 1.399(5) . ? C20 C21 1.410(5) . ? C21 C22 1.384(6) . ? C22 C23 1.389(5) . ? C22 C28 1.439(5) . ? C23 C24 1.399(5) . ? C24 C36 1.501(5) . ? C25 C26 1.459(6) . ? C26 C27 1.539(6) . ? C28 C29 1.205(5) . ? C29 C30 1.442(5) . ? C30 C31 1.378(6) . ? C30 C35 1.396(6) . ? C31 C32 1.394(5) . ? C32 C33 1.377(6) . ? C33 C34 1.359(7) . ? C34 C35 1.384(6) . ? C36 C38 1.516(4) . ? C37 C42 1.394(5) . ? C37 C38 1.395(5) . ? C38 C39 1.390(4) . ? C39 C40 1.397(5) . ? C40 C41 1.400(5) . ? C40 C46 1.438(5) . ? C41 C42 1.383(5) . ? C42 C54 1.526(4) . ? C43 C44 1.510(5) . ? C44 C45 1.508(6) . ? C46 C47 1.182(5) . ? C47 C48 1.443(5) . ? C48 C49 1.381(6) . ? C48 C53 1.399(6) . ? C49 C50 1.381(5) . ? C50 C51 1.360(7) . ? C51 C52 1.374(7) . ? C52 C53 1.393(6) . ? C54 C56 1.503(6) . ? C55 C60 1.390(6) . ? C55 C56 1.392(5) . ? C56 C57 1.404(5) . ? C57 C58 1.375(6) . ? C58 C59 1.385(6) . ? C58 C64 1.456(5) . ? C59 C60 1.394(5) . ? C60 C72 1.516(6) . ? C61 C62 1.492(6) . ? C62 C63 1.524(5) . ? C64 C65 1.176(5) . ? C65 C66 1.447(5) . ? C66 C67 1.387(6) . ? C66 C71 1.401(5) . ? C67 C68 1.389(5) . ? C68 C69 1.373(5) . ? C69 C70 1.386(5) . ? C70 C71 1.384(5) . ? C1LA C2LA 1.389(6) . ? C1LA C6LA 1.391(6) . ? C1LA C7LA 1.498(6) . ? C2LA C3LA 1.369(7) . ? C3LA C4LA 1.388(7) . ? C4LA C5LA 1.382(6) . ? C5LA C6LA 1.380(6) . ? C1LB C2LB 1.379(6) . ? C1LB C6LB 1.383(7) . ? C1LB C7LB 1.502(6) . ? C2LB C3LB 1.379(6) . ? C3LB C4LB 1.372(6) . ? C4LB C5LB 1.380(7) . ? C5LB C6LB 1.361(7) . ? C1LC C2LC 1.3900 . ? C1LC C6LC 1.3900 . ? C1LC C7LC 1.460(15) . ? C2LC C3LC 1.3900 . ? C3LC C4LC 1.3900 . ? C4LC C5LC 1.3900 . ? C5LC C6LC 1.3900 . ? 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 C7 111.7(3) . . ? O1 C1 C2 119.1(3) . . ? O1 C1 C6 119.3(3) . . ? C2 C1 C6 121.5(3) . . ? O3 N1 O2 123.8(4) . . ? O3 N1 C15 118.2(4) . . ? O2 N1 C15 118.0(3) . . ? C3 C2 C1 118.5(3) . . ? C3 C2 C72 119.8(3) . . ? C1 C2 C72 121.6(3) . . ? O5 N2 O6 123.4(4) . . ? O5 N2 C33 119.1(4) . . ? O6 N2 C33 117.5(4) . . ? C2 C3 C4 121.0(4) . . ? O9 N3 O8 124.5(5) . . ? O9 N3 C51 118.3(6) . . ? O8 N3 C51 117.2(5) . . ? C19 O4 C25 117.1(3) . . ? C5 C4 C3 119.3(4) . . ? C5 C4 C10 119.7(3) . . ? C3 C4 C10 121.0(4) . . ? O11 N4 O12 124.1(3) . . ? O11 N4 C69 117.7(3) . . ? O12 N4 C69 118.2(3) . . ? C6 C5 C4 121.1(4) . . ? C5 C6 C1 118.4(3) . . ? C5 C6 C18 119.1(3) . . ? C1 C6 C18 122.4(3) . . ? C37 O7 C43 112.6(3) . . ? O1 C7 C8 108.3(4) . . ? C9 C8 C7 113.5(5) . . ? C55 O10 C61 115.0(3) . . ? C11 C10 C4 178.1(5) . . ? C10 C11 C12 177.4(5) . . ? C17 C12 C13 119.2(4) . . ? C17 C12 C11 119.4(3) . . ? C13 C12 C11 121.3(4) . . ? C14 C13 C12 121.0(4) . . ? C13 C14 C15 118.5(4) . . ? C16 C15 C14 122.1(4) . . ? C16 C15 N1 118.0(4) . . ? C14 C15 N1 119.9(4) . . ? C17 C16 C15 118.8(4) . . ? C16 C17 C12 120.2(3) . . ? C20 C18 C6 109.6(3) . . ? O4 C19 C24 117.2(3) . . ? O4 C19 C20 119.7(3) . . ? C24 C19 C20 122.8(3) . . ? C19 C20 C21 117.2(4) . . ? C19 C20 C18 121.1(3) . . ? C21 C20 C18 121.3(3) . . ? C22 C21 C20 121.1(3) . . ? C21 C22 C23 119.6(3) . . ? C21 C22 C28 121.7(3) . . ? C23 C22 C28 118.6(4) . . ? C22 C23 C24 121.2(4) . . ? C19 C24 C23 117.8(3) . . ? C19 C24 C36 120.9(3) . . ? C23 C24 C36 121.2(3) . . ? O4 C25 C26 114.0(4) . . ? C25 C26 C27 112.1(4) . . ? C29 C28 C22 175.5(5) . . ? C28 C29 C30 178.2(4) . . ? C31 C30 C35 120.0(3) . . ? C31 C30 C29 120.8(3) . . ? C35 C30 C29 119.2(4) . . ? C30 C31 C32 120.7(4) . . ? C33 C32 C31 117.5(4) . . ? C34 C33 C32 122.9(4) . . ? C34 C33 N2 119.2(4) . . ? C32 C33 N2 117.9(4) . . ? C33 C34 C35 119.4(4) . . ? C34 C35 C30 119.2(4) . . ? C24 C36 C38 110.8(3) . . ? O7 C37 C42 118.8(3) . . ? O7 C37 C38 118.9(3) . . ? C42 C37 C38 122.3(3) . . ? C39 C38 C37 118.2(3) . . ? C39 C38 C36 119.3(3) . . ? C37 C38 C36 122.4(3) . . ? C38 C39 C40 120.8(3) . . ? C39 C40 C41 119.2(3) . . ? C39 C40 C46 119.3(3) . . ? C41 C40 C46 121.4(3) . . ? C42 C41 C40 121.1(3) . . ? C41 C42 C37 118.2(3) . . ? C41 C42 C54 120.0(3) . . ? C37 C42 C54 121.7(3) . . ? O7 C43 C44 108.5(3) . . ? C45 C44 C43 113.1(4) . . ? C47 C46 C40 177.7(4) . . ? C46 C47 C48 176.6(4) . . ? C49 C48 C53 119.9(4) . . ? C49 C48 C47 119.8(4) . . ? C53 C48 C47 120.2(4) . . ? C48 C49 C50 120.8(4) . . ? C51 C50 C49 118.3(5) . . ? C50 C51 C52 123.2(4) . . ? C50 C51 N3 118.7(5) . . ? C52 C51 N3 118.1(5) . . ? C51 C52 C53 118.5(4) . . ? C52 C53 C48 119.2(5) . . ? C56 C54 C42 110.3(3) . . ? O10 C55 C60 117.9(3) . . ? O10 C55 C56 119.2(4) . . ? C60 C55 C56 122.8(3) . . ? C55 C56 C57 116.9(4) . . ? C55 C56 C54 121.7(3) . . ? C57 C56 C54 121.1(3) . . ? C58 C57 C56 121.4(4) . . ? C57 C58 C59 119.9(3) . . ? C57 C58 C64 118.4(4) . . ? C59 C58 C64 121.7(4) . . ? C58 C59 C60 120.8(4) . . ? C55 C60 C59 117.8(4) . . ? C55 C60 C72 120.8(3) . . ? C59 C60 C72 121.3(4) . . ? O10 C61 C62 112.5(3) . . ? C61 C62 C63 111.5(4) . . ? C65 C64 C58 175.4(5) . . ? C64 C65 C66 174.4(4) . . ? C67 C66 C71 120.0(3) . . ? C67 C66 C65 118.4(3) . . ? C71 C66 C65 121.7(4) . . ? C66 C67 C68 120.3(3) . . ? C69 C68 C67 118.5(4) . . ? C68 C69 C70 122.7(3) . . ? C68 C69 N4 118.9(3) . . ? C70 C69 N4 118.4(3) . . ? C71 C70 C69 118.5(3) . . ? C70 C71 C66 120.0(4) . . ? C60 C72 C2 110.3(3) . . ? C2LA C1LA C6LA 117.8(4) . . ? C2LA C1LA C7LA 121.4(4) . . ? C6LA C1LA C7LA 120.7(4) . . ? C3LA C2LA C1LA 121.3(4) . . ? C2LA C3LA C4LA 120.7(4) . . ? C5LA C4LA C3LA 118.5(4) . . ? C6LA C5LA C4LA 120.8(4) . . ? C5LA C6LA C1LA 120.8(4) . . ? C2LB C1LB C6LB 117.8(4) . . ? C2LB C1LB C7LB 122.1(5) . . ? C6LB C1LB C7LB 120.0(5) . . ? C3LB C2LB C1LB 121.4(4) . . ? C4LB C3LB C2LB 119.9(4) . . ? C3LB C4LB C5LB 119.1(4) . . ? C6LB C5LB C4LB 120.8(4) . . ? C5LB C6LB C1LB 121.0(4) . . ? C2LC C1LC C6LC 120.0 . . ? C2LC C1LC C7LC 121.4(8) . . ? C6LC C1LC C7LC 118.6(8) . . ? C3LC C2LC C1LC 120.0 . . ? C4LC C3LC C2LC 120.0 . . ? C3LC C4LC C5LC 120.0 . . ? C6LC C5LC C4LC 120.0 . . ? C5LC C6LC C1LC 120.0 . . ? 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 C7 O1 C1 C2 -90.7(4) . . . . ? C7 O1 C1 C6 89.8(4) . . . . ? O1 C1 C2 C3 176.2(4) . . . . ? C6 C1 C2 C3 -4.3(6) . . . . ? O1 C1 C2 C72 -5.5(6) . . . . ? C6 C1 C2 C72 174.0(4) . . . . ? C1 C2 C3 C4 1.6(6) . . . . ? C72 C2 C3 C4 -176.8(4) . . . . ? C2 C3 C4 C5 1.6(6) . . . . ? C2 C3 C4 C10 -178.4(4) . . . . ? C3 C4 C5 C6 -2.2(6) . . . . ? C10 C4 C5 C6 177.8(4) . . . . ? C4 C5 C6 C1 -0.4(6) . . . . ? C4 C5 C6 C18 175.6(4) . . . . ? O1 C1 C6 C5 -176.8(3) . . . . ? C2 C1 C6 C5 3.7(6) . . . . ? O1 C1 C6 C18 7.4(6) . . . . ? C2 C1 C6 C18 -172.1(4) . . . . ? C1 O1 C7 C8 178.8(4) . . . . ? O1 C7 C8 C9 66.6(5) . . . . ? C5 C4 C10 C11 -76(13) . . . . ? C3 C4 C10 C11 104(13) . . . . ? C4 C10 C11 C12 17(22) . . . . ? C10 C11 C12 C17 59(11) . . . . ? C10 C11 C12 C13 -119(11) . . . . ? C17 C12 C13 C14 -0.6(7) . . . . ? C11 C12 C13 C14 177.5(4) . . . . ? C12 C13 C14 C15 0.7(7) . . . . ? C13 C14 C15 C16 -0.8(7) . . . . ? C13 C14 C15 N1 -179.2(4) . . . . ? O3 N1 C15 C16 -171.5(4) . . . . ? O2 N1 C15 C16 7.7(6) . . . . ? O3 N1 C15 C14 6.9(6) . . . . ? O2 N1 C15 C14 -173.9(4) . . . . ? C14 C15 C16 C17 0.8(7) . . . . ? N1 C15 C16 C17 179.2(4) . . . . ? C15 C16 C17 C12 -0.8(6) . . . . ? C13 C12 C17 C16 0.7(6) . . . . ? C11 C12 C17 C16 -177.5(4) . . . . ? C5 C6 C18 C20 -56.7(5) . . . . ? C1 C6 C18 C20 119.1(4) . . . . ? C25 O4 C19 C24 112.4(4) . . . . ? C25 O4 C19 C20 -73.3(4) . . . . ? O4 C19 C20 C21 -179.9(3) . . . . ? C24 C19 C20 C21 -5.9(5) . . . . ? O4 C19 C20 C18 -7.1(5) . . . . ? C24 C19 C20 C18 166.9(3) . . . . ? C6 C18 C20 C19 -66.4(4) . . . . ? C6 C18 C20 C21 106.2(4) . . . . ? C19 C20 C21 C22 2.8(5) . . . . ? C18 C20 C21 C22 -170.1(3) . . . . ? C20 C21 C22 C23 1.3(5) . . . . ? C20 C21 C22 C28 179.8(3) . . . . ? C21 C22 C23 C24 -2.4(5) . . . . ? C28 C22 C23 C24 179.0(3) . . . . ? O4 C19 C24 C23 179.0(3) . . . . ? C20 C19 C24 C23 4.9(5) . . . . ? O4 C19 C24 C36 2.5(4) . . . . ? C20 C19 C24 C36 -171.7(3) . . . . ? C22 C23 C24 C19 -0.5(5) . . . . ? C22 C23 C24 C36 176.0(3) . . . . ? C19 O4 C25 C26 -100.0(4) . . . . ? O4 C25 C26 C27 -168.3(3) . . . . ? C21 C22 C28 C29 172(5) . . . . ? C23 C22 C28 C29 -9(5) . . . . ? C22 C28 C29 C30 -86(15) . . . . ? C28 C29 C30 C31 81(14) . . . . ? C28 C29 C30 C35 -99(14) . . . . ? C35 C30 C31 C32 4.0(5) . . . . ? C29 C30 C31 C32 -175.8(3) . . . . ? C30 C31 C32 C33 -0.5(5) . . . . ? C31 C32 C33 C34 -3.4(6) . . . . ? C31 C32 C33 N2 175.3(3) . . . . ? O5 N2 C33 C34 -177.8(4) . . . . ? O6 N2 C33 C34 4.5(7) . . . . ? O5 N2 C33 C32 3.4(6) . . . . ? O6 N2 C33 C32 -174.3(5) . . . . ? C32 C33 C34 C35 3.7(7) . . . . ? N2 C33 C34 C35 -175.0(4) . . . . ? C33 C34 C35 C30 -0.1(7) . . . . ? C31 C30 C35 C34 -3.7(6) . . . . ? C29 C30 C35 C34 176.1(4) . . . . ? C19 C24 C36 C38 70.5(4) . . . . ? C23 C24 C36 C38 -105.9(4) . . . . ? C43 O7 C37 C42 82.0(4) . . . . ? C43 O7 C37 C38 -99.0(4) . . . . ? O7 C37 C38 C39 177.6(3) . . . . ? C42 C37 C38 C39 -3.5(6) . . . . ? O7 C37 C38 C36 -5.2(5) . . . . ? C42 C37 C38 C36 173.7(4) . . . . ? C24 C36 C38 C39 58.7(5) . . . . ? C24 C36 C38 C37 -118.4(4) . . . . ? C37 C38 C39 C40 0.3(6) . . . . ? C36 C38 C39 C40 -176.9(4) . . . . ? C38 C39 C40 C41 2.0(6) . . . . ? C38 C39 C40 C46 -179.1(4) . . . . ? C39 C40 C41 C42 -1.4(6) . . . . ? C46 C40 C41 C42 179.7(4) . . . . ? C40 C41 C42 C37 -1.5(6) . . . . ? C40 C41 C42 C54 175.6(4) . . . . ? O7 C37 C42 C41 -177.0(3) . . . . ? C38 C37 C42 C41 4.1(6) . . . . ? O7 C37 C42 C54 5.9(5) . . . . ? C38 C37 C42 C54 -173.0(3) . . . . ? C37 O7 C43 C44 -168.6(3) . . . . ? O7 C43 C44 C45 173.4(3) . . . . ? C39 C40 C46 C47 -4(12) . . . . ? C41 C40 C46 C47 175(100) . . . . ? C40 C46 C47 C48 16(18) . . . . ? C46 C47 C48 C49 45(8) . . . . ? C46 C47 C48 C53 -133(8) . . . . ? C53 C48 C49 C50 1.0(6) . . . . ? C47 C48 C49 C50 -177.1(4) . . . . ? C48 C49 C50 C51 -0.6(6) . . . . ? C49 C50 C51 C52 0.1(6) . . . . ? C49 C50 C51 N3 180.0(4) . . . . ? O9 N3 C51 C50 -178.7(5) . . . . ? O8 N3 C51 C50 1.2(6) . . . . ? O9 N3 C51 C52 1.2(7) . . . . ? O8 N3 C51 C52 -178.9(4) . . . . ? C50 C51 C52 C53 0.1(6) . . . . ? N3 C51 C52 C53 -179.8(3) . . . . ? C51 C52 C53 C48 0.2(6) . . . . ? C49 C48 C53 C52 -0.7(5) . . . . ? C47 C48 C53 C52 177.3(3) . . . . ? C41 C42 C54 C56 -60.1(4) . . . . ? C37 C42 C54 C56 116.9(4) . . . . ? C61 O10 C55 C60 109.3(4) . . . . ? C61 O10 C55 C56 -74.7(4) . . . . ? O10 C55 C56 C57 177.9(3) . . . . ? C60 C55 C56 C57 -6.4(5) . . . . ? O10 C55 C56 C54 -7.9(5) . . . . ? C60 C55 C56 C54 167.9(3) . . . . ? C42 C54 C56 C55 -65.8(4) . . . . ? C42 C54 C56 C57 108.1(3) . . . . ? C55 C56 C57 C58 2.1(5) . . . . ? C54 C56 C57 C58 -172.1(3) . . . . ? C56 C57 C58 C59 2.9(5) . . . . ? C56 C57 C58 C64 -179.7(3) . . . . ? C57 C58 C59 C60 -4.0(5) . . . . ? C64 C58 C59 C60 178.7(4) . . . . ? O10 C55 C60 C59 -178.8(3) . . . . ? C56 C55 C60 C59 5.3(5) . . . . ? O10 C55 C60 C72 4.7(5) . . . . ? C56 C55 C60 C72 -171.1(3) . . . . ? C58 C59 C60 C55 0.0(5) . . . . ? C58 C59 C60 C72 176.5(3) . . . . ? C55 O10 C61 C62 -94.1(4) . . . . ? O10 C61 C62 C63 -175.0(3) . . . . ? C57 C58 C64 C65 20(6) . . . . ? C59 C58 C64 C65 -163(6) . . . . ? C58 C64 C65 C66 37(10) . . . . ? C64 C65 C66 C67 -16(5) . . . . ? C64 C65 C66 C71 164(5) . . . . ? C71 C66 C67 C68 -1.6(6) . . . . ? C65 C66 C67 C68 178.8(4) . . . . ? C66 C67 C68 C69 0.1(6) . . . . ? C67 C68 C69 C70 1.3(6) . . . . ? C67 C68 C69 N4 -178.1(4) . . . . ? O11 N4 C69 C68 2.5(6) . . . . ? O12 N4 C69 C68 -177.4(4) . . . . ? O11 N4 C69 C70 -176.9(4) . . . . ? O12 N4 C69 C70 3.2(6) . . . . ? C68 C69 C70 C71 -1.3(6) . . . . ? N4 C69 C70 C71 178.1(4) . . . . ? C69 C70 C71 C66 -0.2(6) . . . . ? C67 C66 C71 C70 1.6(6) . . . . ? C65 C66 C71 C70 -178.8(4) . . . . ? C55 C60 C72 C2 67.4(4) . . . . ? C59 C60 C72 C2 -108.9(4) . . . . ? C3 C2 C72 C60 58.3(5) . . . . ? C1 C2 C72 C60 -120.0(4) . . . . ? C6LA C1LA C2LA C3LA -0.1(7) . . . . ? C7LA C1LA C2LA C3LA -179.7(5) . . . . ? C1LA C2LA C3LA C4LA 1.0(8) . . . . ? C2LA C3LA C4LA C5LA -1.3(8) . . . . ? C3LA C4LA C5LA C6LA 0.7(7) . . . . ? C4LA C5LA C6LA C1LA 0.2(7) . . . . ? C2LA C1LA C6LA C5LA -0.5(7) . . . . ? C7LA C1LA C6LA C5LA 179.1(5) . . . . ? C6LB C1LB C2LB C3LB -0.7(7) . . . . ? C7LB C1LB C2LB C3LB -180.0(5) . . . . ? C1LB C2LB C3LB C4LB 1.5(7) . . . . ? C2LB C3LB C4LB C5LB -0.6(7) . . . . ? C3LB C4LB C5LB C6LB -1.0(8) . . . . ? C4LB C5LB C6LB C1LB 1.9(8) . . . . ? C2LB C1LB C6LB C5LB -1.0(7) . . . . ? C7LB C1LB C6LB C5LB 178.3(5) . . . . ? C6LC C1LC C2LC C3LC 0.0 . . . . ? C7LC C1LC C2LC C3LC -178.3(10) . . . . ? C1LC C2LC C3LC C4LC 0.0 . . . . ? C2LC C3LC C4LC C5LC 0.0 . . . . ? C3LC C4LC C5LC C6LC 0.0 . . . . ? C4LC C5LC C6LC C1LC 0.0 . . . . ? C2LC C1LC C6LC C5LC 0.0 . . . . ? C7LC C1LC C6LC C5LC 178.4(10) . . . . ? _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.963 _refine_diff_density_max 0.525 _refine_diff_density_min -0.389 _refine_diff_density_rms 0.096