data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Dr Philip Gale' _publ_contact_author_address ; School of Chemistry University of Southampton Southampton Hampshire SO17 1BJ UNITED KINGDOM ; _publ_contact_author_email PHILIP.GALE@SOTON.AC.UK _publ_section_title ; 'Twisted' isophthalamide analogues ; loop_ _publ_author_name 'Philip Gale' 'Simon J. Brooks' 'Louise S. Evans' 'Michael B. Hursthouse' 'Mark E. Light' #===END data_03sot0175 _database_code_depnum_ccdc_archive 'CCDC 246437' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H26 N2 O8' _chemical_formula_weight 566.55 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' O O 0.0106 0.0060 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.634(5) _cell_length_b 14.312(6) _cell_length_c 17.706(13) _cell_angle_alpha 95.07(7) _cell_angle_beta 104.67(4) _cell_angle_gamma 91.17(4) _cell_volume 2594(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 10784 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Needle _exptl_crystal_colour 'Pale Yellow' _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.451 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1184 _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9681 _exptl_absorpt_correction_T_max 0.9968 _exptl_absorpt_process_details 'SORTAV (Blessing, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker Nonius FR591 Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Nonius Kappa CCD Area detector' _diffrn_measurement_method '\f and \w scans to fill the asymmetric unit' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 37176 _diffrn_reflns_av_R_equivalents 0.1592 _diffrn_reflns_av_sigmaI/netI 0.1517 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 25.03 _reflns_number_total 8983 _reflns_number_gt 4565 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1999)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'CAMERON (Watkin, et al., 1993)' _computing_publication_material 'WINGX (Farrugia, 1998)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The crystal quality was low and the resulting defraction pattern slightly messy, this has led to slightly higher than average R factors. ; _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^)+(0.0693P)^2^+1.9584P] 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 SHELXL _refine_ls_extinction_coef 0.0121(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 8983 _refine_ls_number_parameters 766 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1727 _refine_ls_R_factor_gt 0.0801 _refine_ls_wR_factor_ref 0.1986 _refine_ls_wR_factor_gt 0.1592 _refine_ls_goodness_of_fit_ref 0.990 _refine_ls_restrained_S_all 0.990 _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 0.8199(3) 0.3198(2) 0.25849(18) 0.0314(8) Uani 1 1 d . . . O2 O 0.9102(3) 0.0098(2) 0.40821(19) 0.0401(9) Uani 1 1 d . . . O3 O 0.9539(3) 0.47916(19) 0.37898(18) 0.0289(8) Uani 1 1 d . . . O4 O 0.6000(3) 0.5397(2) 0.09999(18) 0.0339(8) Uani 1 1 d . . . O5 O 0.6580(3) 0.7846(2) 0.2973(2) 0.0404(9) Uani 1 1 d . . . O6 O 0.9560(3) 0.1843(2) 0.65671(18) 0.0299(8) Uani 1 1 d . . . O7 O 1.0621(3) 0.54789(19) 0.91785(18) 0.0310(8) Uani 1 1 d . . . O8 O 1.0169(3) 0.2284(2) 0.93409(18) 0.0354(8) Uani 1 1 d . . . N1 N 0.7366(3) 0.4637(2) 0.3679(2) 0.0249(9) Uani 1 1 d . . . H1 H 0.6786 0.4410 0.3882 0.030 Uiso 1 1 calc R . . N2 N 0.9914(3) 0.3420(2) 0.6789(2) 0.0247(9) Uani 1 1 d . . . H2 H 0.9985 0.3920 0.6564 0.030 Uiso 1 1 calc R . . C1 C 0.8307(4) 0.2492(3) 0.2935(3) 0.0238(10) Uani 1 1 d . . . C2 C 0.8067(4) 0.1545(3) 0.2495(3) 0.0263(11) Uani 1 1 d . . . C3 C 0.7586(4) 0.1473(3) 0.1680(3) 0.0305(11) Uani 1 1 d . . . H3 H 0.7415 0.2013 0.1422 0.037 Uiso 1 1 calc R . . C4 C 0.7366(5) 0.0602(3) 0.1258(3) 0.0340(12) Uani 1 1 d . . . H4 H 0.7043 0.0553 0.0716 0.041 Uiso 1 1 calc R . . C5 C 0.7626(4) -0.0204(3) 0.1646(3) 0.0340(12) Uani 1 1 d . . . H5 H 0.7474 -0.0790 0.1360 0.041 Uiso 1 1 calc R . . C6 C 0.8108(4) -0.0144(3) 0.2453(3) 0.0300(12) Uani 1 1 d . . . H6 H 0.8285 -0.0685 0.2709 0.036 Uiso 1 1 calc R . . C7 C 0.8326(4) 0.0738(3) 0.2876(3) 0.0268(11) Uani 1 1 d . . . C8 C 0.8814(4) 0.0802(3) 0.3740(3) 0.0263(11) Uani 1 1 d . . . C9 C 0.8937(4) 0.1747(3) 0.4189(3) 0.0237(10) Uani 1 1 d . . . C10 C 0.9299(4) 0.1799(3) 0.4995(3) 0.0233(10) Uani 1 1 d . . . H10 H 0.9508 0.1254 0.5241 0.028 Uiso 1 1 calc R . . C11 C 0.9358(4) 0.2653(3) 0.5448(3) 0.0205(10) Uani 1 1 d . . . C12 C 0.9097(4) 0.3467(3) 0.5064(3) 0.0236(10) Uani 1 1 d . . . H12 H 0.9137 0.4044 0.5357 0.028 Uiso 1 1 calc R . . C13 C 0.8778(4) 0.3426(3) 0.4245(3) 0.0229(10) Uani 1 1 d . . . C14 C 0.8676(4) 0.2560(3) 0.3804(3) 0.0223(10) Uani 1 1 d . . . C15 C 0.8585(4) 0.4346(3) 0.3875(3) 0.0231(10) Uani 1 1 d . . . C16 C 0.7027(4) 0.5329(3) 0.3131(3) 0.0243(11) Uani 1 1 d . . . C17 C 0.6684(4) 0.5005(3) 0.2345(3) 0.0275(11) Uani 1 1 d . . . H17 H 0.6684 0.4367 0.2189 0.033 Uiso 1 1 calc R . . C18 C 0.6340(4) 0.5643(3) 0.1793(3) 0.0288(11) Uani 1 1 d . . . C19 C 0.6328(4) 0.6584(3) 0.2027(3) 0.0307(12) Uani 1 1 d . . . H19 H 0.6092 0.7009 0.1652 0.037 Uiso 1 1 calc R . . C20 C 0.6663(4) 0.6902(3) 0.2812(3) 0.0282(11) Uani 1 1 d . . . C21 C 0.7031(4) 0.6276(3) 0.3381(3) 0.0270(11) Uani 1 1 d . . . H21 H 0.7271 0.6487 0.3912 0.032 Uiso 1 1 calc R . . C22 C 0.6084(5) 0.4427(3) 0.0745(3) 0.0366(12) Uani 1 1 d . . . H22A H 0.6972 0.4251 0.0907 0.055 Uiso 1 1 calc R . . H22B H 0.5786 0.4333 0.0184 0.055 Uiso 1 1 calc R . . H22C H 0.5552 0.4048 0.0974 0.055 Uiso 1 1 calc R . . C23 C 0.6960(5) 0.8219(3) 0.3772(3) 0.0337(12) Uani 1 1 d . . . H23A H 0.6470 0.7898 0.4065 0.051 Uiso 1 1 calc R . . H23B H 0.6795 0.8877 0.3809 0.051 Uiso 1 1 calc R . . H23C H 0.7871 0.8135 0.3981 0.051 Uiso 1 1 calc R . . C24 C 0.9621(4) 0.2611(3) 0.6318(3) 0.0224(10) Uani 1 1 d . . . C25 C 1.0117(4) 0.3536(3) 0.7613(3) 0.0226(10) Uani 1 1 d . . . C26 C 1.0281(4) 0.4458(3) 0.7969(3) 0.0254(11) Uani 1 1 d . . . H26 H 1.0268 0.4961 0.7670 0.030 Uiso 1 1 calc R . . C27 C 1.0462(4) 0.4612(3) 0.8772(3) 0.0242(10) Uani 1 1 d . . . C28 C 1.0474(4) 0.3869(3) 0.9222(3) 0.0297(11) Uani 1 1 d . . . H28 H 1.0632 0.3977 0.9764 0.036 Uiso 1 1 calc R . . C29 C 1.0253(4) 0.2975(3) 0.8863(3) 0.0257(11) Uani 1 1 d . . . C30 C 1.0102(4) 0.2782(3) 0.8059(3) 0.0253(11) Uani 1 1 d . . . H30 H 0.9994 0.2167 0.7826 0.030 Uiso 1 1 calc R . . C31 C 1.0253(5) 0.6269(3) 0.8742(3) 0.0374(13) Uani 1 1 d . . . H31A H 1.0857 0.6370 0.8433 0.056 Uiso 1 1 calc R . . H31B H 1.0261 0.6817 0.9098 0.056 Uiso 1 1 calc R . . H31C H 0.9394 0.6149 0.8403 0.056 Uiso 1 1 calc R . . C32 C 0.9659(5) 0.1382(3) 0.8975(3) 0.0347(12) Uani 1 1 d . . . H32A H 0.8873 0.1449 0.8577 0.052 Uiso 1 1 calc R . . H32B H 0.9475 0.1006 0.9360 0.052 Uiso 1 1 calc R . . H32C H 1.0286 0.1082 0.8740 0.052 Uiso 1 1 calc R . . O9 O 0.7047(3) 0.1781(2) 0.74115(18) 0.0294(8) Uani 1 1 d . . . O10 O 0.5363(3) 0.4810(2) 0.59496(18) 0.0314(8) Uani 1 1 d . . . O11 O 0.5531(3) 0.01880(19) 0.61643(18) 0.0281(8) Uani 1 1 d . . . O12 O 0.9004(3) -0.1941(2) 0.81396(19) 0.0352(8) Uani 1 1 d . . . O13 O 0.7604(3) -0.2935(2) 0.54218(19) 0.0342(8) Uani 1 1 d . . . O14 O 0.5480(3) 0.31217(19) 0.34280(17) 0.0285(8) Uani 1 1 d . . . O15 O 0.4287(3) -0.0499(2) 0.08537(18) 0.0337(8) Uani 1 1 d . . . O16 O 0.3769(3) 0.2767(2) 0.07424(18) 0.0347(8) Uani 1 1 d . . . N3 N 0.7684(4) 0.0316(2) 0.6213(2) 0.0257(9) Uani 1 1 d . . . H3A H 0.8311 0.0671 0.6158 0.031 Uiso 1 1 calc R . . N4 N 0.4919(3) 0.1562(2) 0.3241(2) 0.0253(9) Uani 1 1 d . . . H4A H 0.4827 0.1075 0.3477 0.030 Uiso 1 1 calc R . . C33 C 0.6728(4) 0.2485(3) 0.7087(3) 0.0249(11) Uani 1 1 d . . . C34 C 0.6765(4) 0.3413(3) 0.7530(3) 0.0233(10) Uani 1 1 d . . . C35 C 0.7214(4) 0.3500(3) 0.8344(3) 0.0287(11) Uani 1 1 d . . . H35 H 0.7468 0.2971 0.8604 0.034 Uiso 1 1 calc R . . C36 C 0.7286(4) 0.4365(3) 0.8771(3) 0.0299(11) Uani 1 1 d . . . H36 H 0.7594 0.4420 0.9314 0.036 Uiso 1 1 calc R . . C37 C 0.6895(4) 0.5153(3) 0.8381(3) 0.0301(11) Uani 1 1 d . . . H37 H 0.6947 0.5737 0.8665 0.036 Uiso 1 1 calc R . . C38 C 0.6431(4) 0.5074(3) 0.7580(3) 0.0299(11) Uani 1 1 d . . . H38 H 0.6165 0.5604 0.7325 0.036 Uiso 1 1 calc R . . C39 C 0.6357(4) 0.4213(3) 0.7150(3) 0.0257(11) Uani 1 1 d . . . C40 C 0.5856(4) 0.4150(3) 0.6288(3) 0.0253(11) Uani 1 1 d . . . C41 C 0.5931(4) 0.3237(3) 0.5827(3) 0.0221(10) Uani 1 1 d . . . C42 C 0.5623(4) 0.3193(3) 0.5023(3) 0.0230(10) Uani 1 1 d . . . H42 H 0.5399 0.3736 0.4777 0.028 Uiso 1 1 calc R . . C43 C 0.5639(4) 0.2344(3) 0.4565(3) 0.0224(10) Uani 1 1 d . . . C44 C 0.5965(4) 0.1547(3) 0.4945(3) 0.0236(10) Uani 1 1 d . . . H44 H 0.5977 0.0979 0.4649 0.028 Uiso 1 1 calc R . . C45 C 0.6278(4) 0.1573(3) 0.5766(3) 0.0222(10) Uani 1 1 d . . . C46 C 0.6301(4) 0.2426(3) 0.6207(2) 0.0208(10) Uani 1 1 d . . . C47 C 0.6489(4) 0.0643(3) 0.6093(2) 0.0230(10) Uani 1 1 d . . . C48 C 0.7940(4) -0.0615(3) 0.6430(3) 0.0257(11) Uani 1 1 d . . . C49 C 0.8381(4) -0.0769(3) 0.7214(3) 0.0276(11) Uani 1 1 d . . . H49 H 0.8541 -0.0271 0.7605 0.033 Uiso 1 1 calc R . . C50 C 0.8578(4) -0.1685(3) 0.7400(3) 0.0262(11) Uani 1 1 d . . . C51 C 0.8335(4) -0.2429(3) 0.6813(3) 0.0282(11) Uani 1 1 d . . . H51 H 0.8470 -0.3041 0.6944 0.034 Uiso 1 1 calc R . . C52 C 0.7894(4) -0.2258(3) 0.6034(3) 0.0265(11) Uani 1 1 d . . . C53 C 0.7700(4) -0.1337(3) 0.5838(3) 0.0293(11) Uani 1 1 d . . . H53 H 0.7414 -0.1214 0.5316 0.035 Uiso 1 1 calc R . . C54 C 0.9157(5) -0.1229(3) 0.8773(3) 0.0384(13) Uani 1 1 d . . . H54A H 0.9872 -0.0806 0.8778 0.058 Uiso 1 1 calc R . . H54B H 0.9328 -0.1512 0.9259 0.058 Uiso 1 1 calc R . . H54C H 0.8374 -0.0889 0.8711 0.058 Uiso 1 1 calc R . . C55 C 0.7557(5) -0.3885(3) 0.5603(3) 0.0337(12) Uani 1 1 d . . . H55A H 0.8418 -0.4062 0.5852 0.051 Uiso 1 1 calc R . . H55B H 0.7217 -0.4289 0.5129 0.051 Uiso 1 1 calc R . . H55C H 0.7004 -0.3944 0.5951 0.051 Uiso 1 1 calc R . . C56 C 0.5339(4) 0.2370(3) 0.3700(3) 0.0248(11) Uani 1 1 d . . . C57 C 0.4615(4) 0.1433(3) 0.2413(3) 0.0246(11) Uani 1 1 d . . . C58 C 0.4587(4) 0.0516(3) 0.2068(3) 0.0255(11) Uani 1 1 d . . . H58 H 0.4746 0.0016 0.2377 0.031 Uiso 1 1 calc R . . C59 C 0.4321(4) 0.0360(3) 0.1264(3) 0.0273(11) Uani 1 1 d . . . C60 C 0.4056(4) 0.1096(3) 0.0790(3) 0.0262(11) Uani 1 1 d . . . H60 H 0.3884 0.0985 0.0247 0.031 Uiso 1 1 calc R . . C61 C 0.4056(4) 0.1992(3) 0.1144(3) 0.0267(11) Uani 1 1 d . . . C62 C 0.4352(4) 0.2168(3) 0.1956(3) 0.0265(11) Uani 1 1 d . . . H62 H 0.4371 0.2779 0.2189 0.032 Uiso 1 1 calc R . . C63 C 0.4369(5) -0.1296(3) 0.1290(3) 0.0372(13) Uani 1 1 d . . . H63A H 0.5214 -0.1290 0.1650 0.056 Uiso 1 1 calc R . . H63B H 0.4234 -0.1859 0.0938 0.056 Uiso 1 1 calc R . . H63C H 0.3715 -0.1275 0.1578 0.056 Uiso 1 1 calc R . . C64 C 0.3459(5) 0.2640(3) -0.0093(3) 0.0371(13) Uani 1 1 d . . . H64A H 0.4165 0.2351 -0.0257 0.056 Uiso 1 1 calc R . . H64B H 0.3320 0.3239 -0.0298 0.056 Uiso 1 1 calc R . . H64C H 0.2683 0.2245 -0.0286 0.056 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 0.043(2) 0.0256(17) 0.026(2) 0.0048(14) 0.0081(16) 0.0040(15) O2 0.064(2) 0.0229(17) 0.028(2) 0.0048(15) 0.0005(18) 0.0057(16) O3 0.0264(18) 0.0267(17) 0.033(2) 0.0088(14) 0.0050(15) -0.0026(14) O4 0.049(2) 0.0296(17) 0.020(2) 0.0047(14) 0.0024(16) 0.0043(15) O5 0.062(2) 0.0216(17) 0.035(2) 0.0059(15) 0.0065(18) 0.0055(16) O6 0.042(2) 0.0248(17) 0.0222(19) 0.0049(14) 0.0064(15) -0.0037(15) O7 0.045(2) 0.0211(16) 0.026(2) 0.0029(14) 0.0076(16) 0.0008(14) O8 0.053(2) 0.0273(17) 0.023(2) 0.0060(14) 0.0040(16) -0.0086(16) N1 0.027(2) 0.025(2) 0.025(2) 0.0104(17) 0.0091(18) 0.0059(17) N2 0.031(2) 0.021(2) 0.024(2) 0.0066(17) 0.0085(18) -0.0020(16) C1 0.021(2) 0.024(2) 0.029(3) 0.007(2) 0.009(2) 0.0021(19) C2 0.028(3) 0.029(3) 0.023(3) 0.003(2) 0.010(2) -0.002(2) C3 0.034(3) 0.031(3) 0.028(3) 0.008(2) 0.009(2) 0.004(2) C4 0.037(3) 0.040(3) 0.021(3) -0.003(2) 0.002(2) 0.004(2) C5 0.032(3) 0.034(3) 0.035(3) -0.008(2) 0.011(2) -0.005(2) C6 0.033(3) 0.027(3) 0.027(3) -0.001(2) 0.004(2) -0.006(2) C7 0.027(3) 0.023(2) 0.030(3) -0.002(2) 0.008(2) -0.004(2) C8 0.032(3) 0.024(2) 0.024(3) 0.005(2) 0.008(2) 0.001(2) C9 0.026(3) 0.022(2) 0.021(3) 0.0032(19) 0.003(2) 0.003(2) C10 0.026(3) 0.019(2) 0.026(3) 0.009(2) 0.007(2) 0.0013(19) C11 0.018(2) 0.023(2) 0.020(3) 0.0053(19) 0.0026(19) 0.0021(19) C12 0.023(2) 0.025(2) 0.023(3) 0.003(2) 0.006(2) 0.0018(19) C13 0.028(3) 0.018(2) 0.025(3) 0.0065(19) 0.008(2) 0.0011(19) C14 0.023(2) 0.022(2) 0.021(3) 0.003(2) 0.004(2) -0.0010(19) C15 0.032(3) 0.021(2) 0.015(3) 0.0005(18) 0.004(2) 0.000(2) C16 0.021(2) 0.023(2) 0.028(3) 0.011(2) 0.003(2) 0.0026(19) C17 0.027(3) 0.030(3) 0.027(3) 0.006(2) 0.007(2) 0.005(2) C18 0.032(3) 0.031(3) 0.022(3) 0.004(2) 0.006(2) 0.000(2) C19 0.030(3) 0.031(3) 0.032(3) 0.012(2) 0.007(2) 0.007(2) C20 0.034(3) 0.021(2) 0.031(3) 0.010(2) 0.007(2) 0.001(2) C21 0.029(3) 0.029(3) 0.023(3) 0.009(2) 0.004(2) 0.001(2) C22 0.038(3) 0.040(3) 0.030(3) 0.012(2) 0.003(2) 0.008(2) C23 0.039(3) 0.027(3) 0.032(3) 0.003(2) 0.002(2) 0.001(2) C24 0.023(2) 0.021(2) 0.022(3) 0.003(2) 0.004(2) 0.0005(19) C25 0.023(2) 0.027(2) 0.018(3) 0.004(2) 0.006(2) 0.0014(19) C26 0.029(3) 0.026(2) 0.023(3) 0.009(2) 0.009(2) 0.003(2) C27 0.027(3) 0.026(2) 0.017(3) 0.003(2) 0.001(2) 0.005(2) C28 0.034(3) 0.029(3) 0.024(3) 0.004(2) 0.005(2) 0.001(2) C29 0.028(3) 0.028(3) 0.022(3) 0.011(2) 0.006(2) 0.000(2) C30 0.026(3) 0.026(2) 0.023(3) 0.005(2) 0.003(2) 0.002(2) C31 0.058(3) 0.027(3) 0.028(3) 0.004(2) 0.013(3) -0.001(2) C32 0.047(3) 0.025(2) 0.030(3) 0.008(2) 0.005(2) -0.002(2) O9 0.0384(19) 0.0211(16) 0.029(2) 0.0039(14) 0.0085(16) -0.0006(14) O10 0.041(2) 0.0246(17) 0.029(2) 0.0054(15) 0.0090(16) 0.0066(15) O11 0.0316(19) 0.0244(16) 0.028(2) 0.0059(14) 0.0061(15) 0.0003(14) O12 0.049(2) 0.0265(17) 0.027(2) 0.0079(15) 0.0007(16) 0.0040(15) O13 0.047(2) 0.0232(17) 0.033(2) 0.0042(15) 0.0116(17) 0.0028(15) O14 0.042(2) 0.0203(16) 0.0218(19) 0.0069(13) 0.0044(15) -0.0019(14) O15 0.053(2) 0.0224(17) 0.027(2) 0.0044(14) 0.0126(17) 0.0024(15) O16 0.057(2) 0.0263(17) 0.0195(19) 0.0076(14) 0.0051(16) 0.0054(16) N3 0.028(2) 0.021(2) 0.029(2) 0.0057(16) 0.0084(18) -0.0013(17) N4 0.037(2) 0.0190(19) 0.018(2) -0.0014(16) 0.0045(18) -0.0001(17) C33 0.024(3) 0.021(2) 0.031(3) 0.004(2) 0.008(2) -0.002(2) C34 0.019(2) 0.026(2) 0.022(3) 0.004(2) -0.001(2) 0.0032(19) C35 0.029(3) 0.027(3) 0.030(3) 0.001(2) 0.007(2) 0.002(2) C36 0.032(3) 0.030(3) 0.026(3) 0.001(2) 0.006(2) -0.002(2) C37 0.032(3) 0.030(3) 0.027(3) -0.007(2) 0.010(2) -0.003(2) C38 0.026(3) 0.028(3) 0.035(3) 0.005(2) 0.006(2) 0.004(2) C39 0.025(3) 0.026(2) 0.026(3) 0.002(2) 0.007(2) 0.004(2) C40 0.024(2) 0.023(2) 0.030(3) 0.006(2) 0.007(2) 0.001(2) C41 0.022(2) 0.018(2) 0.027(3) 0.0047(19) 0.006(2) -0.0010(19) C42 0.022(2) 0.024(2) 0.022(3) 0.007(2) 0.002(2) -0.0008(19) C43 0.023(2) 0.026(2) 0.018(3) -0.001(2) 0.006(2) -0.0034(19) C44 0.023(2) 0.018(2) 0.028(3) 0.0000(19) 0.005(2) -0.0013(19) C45 0.020(2) 0.020(2) 0.025(3) 0.0065(19) 0.002(2) -0.0008(19) C46 0.022(2) 0.020(2) 0.020(3) 0.0029(19) 0.004(2) 0.0015(19) C47 0.031(3) 0.024(2) 0.012(3) 0.0003(18) 0.003(2) 0.002(2) C48 0.023(2) 0.025(2) 0.030(3) 0.009(2) 0.006(2) -0.001(2) C49 0.034(3) 0.023(2) 0.025(3) 0.001(2) 0.008(2) 0.000(2) C50 0.022(2) 0.032(3) 0.022(3) 0.008(2) 0.000(2) 0.004(2) C51 0.031(3) 0.021(2) 0.035(3) 0.008(2) 0.010(2) 0.003(2) C52 0.029(3) 0.020(2) 0.029(3) 0.000(2) 0.006(2) 0.000(2) C53 0.028(3) 0.028(3) 0.031(3) 0.010(2) 0.005(2) 0.003(2) C54 0.047(3) 0.038(3) 0.025(3) 0.004(2) -0.001(2) 0.009(2) C55 0.044(3) 0.020(2) 0.037(3) 0.005(2) 0.008(3) 0.002(2) C56 0.024(3) 0.024(2) 0.027(3) 0.005(2) 0.008(2) 0.003(2) C57 0.030(3) 0.025(2) 0.019(3) 0.004(2) 0.006(2) 0.002(2) C58 0.025(3) 0.026(2) 0.026(3) 0.005(2) 0.005(2) 0.002(2) C59 0.030(3) 0.024(2) 0.028(3) 0.001(2) 0.009(2) 0.003(2) C60 0.035(3) 0.027(2) 0.019(3) 0.003(2) 0.010(2) 0.004(2) C61 0.033(3) 0.025(2) 0.022(3) 0.007(2) 0.005(2) 0.006(2) C62 0.029(3) 0.025(2) 0.026(3) 0.003(2) 0.007(2) 0.004(2) C63 0.050(3) 0.021(2) 0.044(3) 0.003(2) 0.019(3) 0.002(2) C64 0.054(3) 0.036(3) 0.020(3) 0.004(2) 0.006(2) 0.004(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.223(5) . ? O2 C8 1.225(5) . ? O3 C15 1.237(5) . ? O4 C18 1.370(5) . ? O4 C22 1.433(5) . ? O5 C20 1.365(5) . ? O5 C23 1.421(6) . ? O6 C24 1.227(5) . ? O7 C27 1.363(5) . ? O7 C31 1.430(5) . ? O8 C29 1.372(5) . ? O8 C32 1.424(5) . ? N1 C15 1.340(5) . ? N1 C16 1.435(5) . ? N2 C24 1.347(5) . ? N2 C25 1.415(6) . ? C1 C14 1.482(6) . ? C1 C2 1.486(6) . ? C2 C7 1.387(6) . ? C2 C3 1.396(6) . ? C3 C4 1.380(6) . ? C4 C5 1.391(6) . ? C5 C6 1.385(6) . ? C6 C7 1.394(6) . ? C7 C8 1.479(6) . ? C8 C9 1.493(6) . ? C9 C10 1.374(6) . ? C9 C14 1.398(6) . ? C10 C11 1.393(6) . ? C11 C12 1.399(6) . ? C11 C24 1.500(6) . ? C12 C13 1.398(6) . ? C13 C14 1.393(6) . ? C13 C15 1.515(6) . ? C16 C17 1.381(6) . ? C16 C21 1.387(6) . ? C17 C18 1.383(6) . ? C18 C19 1.376(6) . ? C19 C20 1.378(7) . ? C20 C21 1.394(6) . ? C25 C30 1.394(6) . ? C25 C26 1.399(6) . ? C26 C27 1.383(6) . ? C27 C28 1.382(6) . ? C28 C29 1.365(6) . ? C29 C30 1.394(6) . ? O9 C33 1.216(5) . ? O10 C40 1.220(5) . ? O11 C47 1.237(5) . ? O12 C50 1.359(5) . ? O12 C54 1.422(6) . ? O13 C52 1.357(5) . ? O13 C55 1.428(5) . ? O14 C56 1.238(5) . ? O15 C59 1.367(5) . ? O15 C63 1.425(5) . ? O16 C61 1.368(5) . ? O16 C64 1.425(5) . ? N3 C47 1.336(5) . ? N3 C48 1.432(5) . ? N4 C56 1.352(5) . ? N4 C57 1.413(6) . ? C33 C34 1.475(6) . ? C33 C46 1.503(6) . ? C34 C35 1.392(6) . ? C34 C39 1.400(6) . ? C35 C36 1.383(6) . ? C36 C37 1.390(6) . ? C37 C38 1.372(6) . ? C38 C39 1.379(6) . ? C39 C40 1.477(6) . ? C40 C41 1.493(6) . ? C41 C42 1.374(6) . ? C41 C46 1.407(6) . ? C42 C43 1.402(6) . ? C43 C44 1.382(6) . ? C43 C56 1.487(6) . ? C44 C45 1.403(6) . ? C45 C46 1.386(6) . ? C45 C47 1.496(6) . ? C48 C53 1.376(6) . ? C48 C49 1.388(6) . ? C49 C50 1.387(6) . ? C50 C51 1.391(6) . ? C51 C52 1.385(6) . ? C52 C53 1.399(6) . ? C57 C62 1.374(6) . ? C57 C58 1.394(6) . ? C58 C59 1.377(6) . ? C59 C60 1.393(6) . ? C60 C61 1.376(6) . ? C61 C62 1.392(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C18 O4 C22 116.7(3) . . ? C20 O5 C23 117.6(4) . . ? C27 O7 C31 117.6(3) . . ? C29 O8 C32 117.6(4) . . ? C15 N1 C16 120.1(4) . . ? C24 N2 C25 127.1(4) . . ? O1 C1 C14 121.0(4) . . ? O1 C1 C2 120.4(4) . . ? C14 C1 C2 118.6(4) . . ? C7 C2 C3 119.7(4) . . ? C7 C2 C1 121.2(4) . . ? C3 C2 C1 119.0(4) . . ? C4 C3 C2 120.1(4) . . ? C3 C4 C5 119.8(5) . . ? C6 C5 C4 120.8(4) . . ? C5 C6 C7 119.1(4) . . ? C2 C7 C6 120.5(4) . . ? C2 C7 C8 120.4(4) . . ? C6 C7 C8 119.1(4) . . ? O2 C8 C7 121.1(4) . . ? O2 C8 C9 120.5(4) . . ? C7 C8 C9 118.4(4) . . ? C10 C9 C14 120.6(4) . . ? C10 C9 C8 118.3(4) . . ? C14 C9 C8 121.1(4) . . ? C9 C10 C11 121.1(4) . . ? C10 C11 C12 118.3(4) . . ? C10 C11 C24 116.5(4) . . ? C12 C11 C24 125.1(4) . . ? C13 C12 C11 120.9(4) . . ? C14 C13 C12 119.6(4) . . ? C14 C13 C15 122.7(4) . . ? C12 C13 C15 117.7(4) . . ? C13 C14 C9 119.3(4) . . ? C13 C14 C1 120.9(4) . . ? C9 C14 C1 119.8(4) . . ? O3 C15 N1 123.9(4) . . ? O3 C15 C13 119.4(4) . . ? N1 C15 C13 116.7(4) . . ? C17 C16 C21 121.7(4) . . ? C17 C16 N1 116.7(4) . . ? C21 C16 N1 121.5(4) . . ? C18 C17 C16 119.0(4) . . ? O4 C18 C19 116.0(4) . . ? O4 C18 C17 123.7(4) . . ? C19 C18 C17 120.3(4) . . ? C18 C19 C20 120.4(4) . . ? O5 C20 C19 115.1(4) . . ? O5 C20 C21 124.4(4) . . ? C19 C20 C21 120.6(4) . . ? C16 C21 C20 118.0(4) . . ? O6 C24 N2 123.0(4) . . ? O6 C24 C11 118.5(4) . . ? N2 C24 C11 118.4(4) . . ? C30 C25 C26 120.5(4) . . ? C30 C25 N2 122.7(4) . . ? C26 C25 N2 116.8(4) . . ? C27 C26 C25 119.2(4) . . ? O7 C27 C28 115.1(4) . . ? O7 C27 C26 124.1(4) . . ? C28 C27 C26 120.8(4) . . ? C29 C28 C27 119.4(4) . . ? C28 C29 O8 115.9(4) . . ? C28 C29 C30 121.8(4) . . ? O8 C29 C30 122.3(4) . . ? C29 C30 C25 118.2(4) . . ? C50 O12 C54 117.7(3) . . ? C52 O13 C55 117.2(4) . . ? C59 O15 C63 116.6(4) . . ? C61 O16 C64 118.0(4) . . ? C47 N3 C48 121.2(3) . . ? C56 N4 C57 126.8(4) . . ? O9 C33 C34 122.1(4) . . ? O9 C33 C46 119.7(4) . . ? C34 C33 C46 118.2(4) . . ? C35 C34 C39 118.9(4) . . ? C35 C34 C33 119.6(4) . . ? C39 C34 C33 121.5(4) . . ? C36 C35 C34 120.7(4) . . ? C35 C36 C37 119.4(5) . . ? C38 C37 C36 120.4(4) . . ? C37 C38 C39 120.4(4) . . ? C38 C39 C34 120.1(4) . . ? C38 C39 C40 119.2(4) . . ? C34 C39 C40 120.7(4) . . ? O10 C40 C39 122.1(4) . . ? O10 C40 C41 119.6(4) . . ? C39 C40 C41 118.3(4) . . ? C42 C41 C46 119.9(4) . . ? C42 C41 C40 119.3(4) . . ? C46 C41 C40 120.8(4) . . ? C41 C42 C43 121.3(4) . . ? C44 C43 C42 118.1(4) . . ? C44 C43 C56 124.4(4) . . ? C42 C43 C56 117.5(4) . . ? C43 C44 C45 121.7(4) . . ? C46 C45 C44 119.1(4) . . ? C46 C45 C47 125.0(4) . . ? C44 C45 C47 115.8(4) . . ? C45 C46 C41 119.7(4) . . ? C45 C46 C33 120.2(4) . . ? C41 C46 C33 120.1(4) . . ? O11 C47 N3 124.0(4) . . ? O11 C47 C45 118.3(4) . . ? N3 C47 C45 117.3(4) . . ? C53 C48 C49 122.3(4) . . ? C53 C48 N3 117.5(4) . . ? C49 C48 N3 120.2(4) . . ? C50 C49 C48 118.2(4) . . ? O12 C50 C49 124.7(4) . . ? O12 C50 C51 114.6(4) . . ? C49 C50 C51 120.7(4) . . ? C52 C51 C50 120.0(4) . . ? O13 C52 C51 124.4(4) . . ? O13 C52 C53 115.6(4) . . ? C51 C52 C53 120.0(4) . . ? C48 C53 C52 118.8(4) . . ? O14 C56 N4 122.6(4) . . ? O14 C56 C43 119.4(4) . . ? N4 C56 C43 118.0(4) . . ? C62 C57 C58 120.5(4) . . ? C62 C57 N4 122.4(4) . . ? C58 C57 N4 117.1(4) . . ? C59 C58 C57 119.0(4) . . ? O15 C59 C58 124.9(4) . . ? O15 C59 C60 113.7(4) . . ? C58 C59 C60 121.4(4) . . ? C61 C60 C59 118.5(4) . . ? O16 C61 C60 124.0(4) . . ? O16 C61 C62 114.9(4) . . ? C60 C61 C62 121.1(4) . . ? C57 C62 C61 119.5(4) . . ? 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 C7 172.6(4) . . . . ? C14 C1 C2 C7 -7.5(6) . . . . ? O1 C1 C2 C3 -6.6(6) . . . . ? C14 C1 C2 C3 173.3(4) . . . . ? C7 C2 C3 C4 0.3(7) . . . . ? C1 C2 C3 C4 179.5(4) . . . . ? C2 C3 C4 C5 -0.2(7) . . . . ? C3 C4 C5 C6 -0.1(7) . . . . ? C4 C5 C6 C7 0.3(7) . . . . ? C3 C2 C7 C6 -0.1(7) . . . . ? C1 C2 C7 C6 -179.3(4) . . . . ? C3 C2 C7 C8 -179.0(4) . . . . ? C1 C2 C7 C8 1.8(6) . . . . ? C5 C6 C7 C2 -0.2(7) . . . . ? C5 C6 C7 C8 178.7(4) . . . . ? C2 C7 C8 O2 -176.7(4) . . . . ? C6 C7 C8 O2 4.4(7) . . . . ? C2 C7 C8 C9 3.8(6) . . . . ? C6 C7 C8 C9 -175.0(4) . . . . ? O2 C8 C9 C10 -4.2(6) . . . . ? C7 C8 C9 C10 175.3(4) . . . . ? O2 C8 C9 C14 176.7(4) . . . . ? C7 C8 C9 C14 -3.9(6) . . . . ? C14 C9 C10 C11 2.9(6) . . . . ? C8 C9 C10 C11 -176.2(4) . . . . ? C9 C10 C11 C12 -2.9(6) . . . . ? C9 C10 C11 C24 173.5(4) . . . . ? C10 C11 C12 C13 0.4(6) . . . . ? C24 C11 C12 C13 -175.7(4) . . . . ? C11 C12 C13 C14 2.2(6) . . . . ? C11 C12 C13 C15 -176.6(4) . . . . ? C12 C13 C14 C9 -2.2(6) . . . . ? C15 C13 C14 C9 176.6(4) . . . . ? C12 C13 C14 C1 178.5(4) . . . . ? C15 C13 C14 C1 -2.8(6) . . . . ? C10 C9 C14 C13 -0.3(6) . . . . ? C8 C9 C14 C13 178.8(4) . . . . ? C10 C9 C14 C1 179.0(4) . . . . ? C8 C9 C14 C1 -1.8(6) . . . . ? O1 C1 C14 C13 6.7(6) . . . . ? C2 C1 C14 C13 -173.2(4) . . . . ? O1 C1 C14 C9 -172.7(4) . . . . ? C2 C1 C14 C9 7.4(6) . . . . ? C16 N1 C15 O3 20.2(6) . . . . ? C16 N1 C15 C13 -161.7(4) . . . . ? C14 C13 C15 O3 -93.5(5) . . . . ? C12 C13 C15 O3 85.3(5) . . . . ? C14 C13 C15 N1 88.3(5) . . . . ? C12 C13 C15 N1 -92.9(5) . . . . ? C15 N1 C16 C17 85.4(5) . . . . ? C15 N1 C16 C21 -95.3(5) . . . . ? C21 C16 C17 C18 0.2(7) . . . . ? N1 C16 C17 C18 179.6(4) . . . . ? C22 O4 C18 C19 176.3(4) . . . . ? C22 O4 C18 C17 -3.5(6) . . . . ? C16 C17 C18 O4 179.1(4) . . . . ? C16 C17 C18 C19 -0.7(7) . . . . ? O4 C18 C19 C20 -179.6(4) . . . . ? C17 C18 C19 C20 0.2(7) . . . . ? C23 O5 C20 C19 -177.7(4) . . . . ? C23 O5 C20 C21 3.5(7) . . . . ? C18 C19 C20 O5 -178.2(4) . . . . ? C18 C19 C20 C21 0.6(7) . . . . ? C17 C16 C21 C20 0.6(6) . . . . ? N1 C16 C21 C20 -178.7(4) . . . . ? O5 C20 C21 C16 177.7(4) . . . . ? C19 C20 C21 C16 -1.0(7) . . . . ? C25 N2 C24 O6 -4.0(7) . . . . ? C25 N2 C24 C11 176.0(4) . . . . ? C10 C11 C24 O6 -11.6(6) . . . . ? C12 C11 C24 O6 164.6(4) . . . . ? C10 C11 C24 N2 168.5(4) . . . . ? C12 C11 C24 N2 -15.4(6) . . . . ? C24 N2 C25 C30 3.5(7) . . . . ? C24 N2 C25 C26 -173.7(4) . . . . ? C30 C25 C26 C27 1.7(6) . . . . ? N2 C25 C26 C27 179.0(4) . . . . ? C31 O7 C27 C28 -162.5(4) . . . . ? C31 O7 C27 C26 16.6(6) . . . . ? C25 C26 C27 O7 -179.5(4) . . . . ? C25 C26 C27 C28 -0.4(7) . . . . ? O7 C27 C28 C29 176.5(4) . . . . ? C26 C27 C28 C29 -2.6(7) . . . . ? C27 C28 C29 O8 -174.6(4) . . . . ? C27 C28 C29 C30 4.5(7) . . . . ? C32 O8 C29 C28 166.4(4) . . . . ? C32 O8 C29 C30 -12.7(6) . . . . ? C28 C29 C30 C25 -3.2(7) . . . . ? O8 C29 C30 C25 175.8(4) . . . . ? C26 C25 C30 C29 0.1(6) . . . . ? N2 C25 C30 C29 -177.1(4) . . . . ? O9 C33 C34 C35 2.0(6) . . . . ? C46 C33 C34 C35 -177.0(4) . . . . ? O9 C33 C34 C39 -178.1(4) . . . . ? C46 C33 C34 C39 3.0(6) . . . . ? C39 C34 C35 C36 -1.5(6) . . . . ? C33 C34 C35 C36 178.5(4) . . . . ? C34 C35 C36 C37 0.5(7) . . . . ? C35 C36 C37 C38 0.5(7) . . . . ? C36 C37 C38 C39 -0.5(7) . . . . ? C37 C38 C39 C34 -0.4(7) . . . . ? C37 C38 C39 C40 -179.9(4) . . . . ? C35 C34 C39 C38 1.4(6) . . . . ? C33 C34 C39 C38 -178.6(4) . . . . ? C35 C34 C39 C40 -179.1(4) . . . . ? C33 C34 C39 C40 0.9(6) . . . . ? C38 C39 C40 O10 -8.8(6) . . . . ? C34 C39 C40 O10 171.8(4) . . . . ? C38 C39 C40 C41 172.9(4) . . . . ? C34 C39 C40 C41 -6.6(6) . . . . ? O10 C40 C41 C42 9.6(6) . . . . ? C39 C40 C41 C42 -172.0(4) . . . . ? O10 C40 C41 C46 -169.9(4) . . . . ? C39 C40 C41 C46 8.5(6) . . . . ? C46 C41 C42 C43 1.5(6) . . . . ? C40 C41 C42 C43 -178.0(4) . . . . ? C41 C42 C43 C44 0.5(6) . . . . ? C41 C42 C43 C56 -177.8(4) . . . . ? C42 C43 C44 C45 -0.2(6) . . . . ? C56 C43 C44 C45 178.0(4) . . . . ? C43 C44 C45 C46 -2.1(6) . . . . ? C43 C44 C45 C47 174.5(4) . . . . ? C44 C45 C46 C41 4.1(6) . . . . ? C47 C45 C46 C41 -172.2(4) . . . . ? C44 C45 C46 C33 -175.5(4) . . . . ? C47 C45 C46 C33 8.2(6) . . . . ? C42 C41 C46 C45 -3.9(6) . . . . ? C40 C41 C46 C45 175.6(4) . . . . ? C42 C41 C46 C33 175.8(4) . . . . ? C40 C41 C46 C33 -4.7(6) . . . . ? O9 C33 C46 C45 -0.3(6) . . . . ? C34 C33 C46 C45 178.6(4) . . . . ? O9 C33 C46 C41 -180.0(4) . . . . ? C34 C33 C46 C41 -1.0(6) . . . . ? C48 N3 C47 O11 0.7(7) . . . . ? C48 N3 C47 C45 -172.1(4) . . . . ? C46 C45 C47 O11 89.9(5) . . . . ? C44 C45 C47 O11 -86.4(5) . . . . ? C46 C45 C47 N3 -96.9(5) . . . . ? C44 C45 C47 N3 86.7(5) . . . . ? C47 N3 C48 C53 83.8(5) . . . . ? C47 N3 C48 C49 -94.6(5) . . . . ? C53 C48 C49 C50 -0.3(7) . . . . ? N3 C48 C49 C50 178.0(4) . . . . ? C54 O12 C50 C49 5.5(6) . . . . ? C54 O12 C50 C51 -174.3(4) . . . . ? C48 C49 C50 O12 -179.9(4) . . . . ? C48 C49 C50 C51 -0.1(6) . . . . ? O12 C50 C51 C52 179.9(4) . . . . ? C49 C50 C51 C52 0.0(7) . . . . ? C55 O13 C52 C51 10.3(6) . . . . ? C55 O13 C52 C53 -168.7(4) . . . . ? C50 C51 C52 O13 -178.6(4) . . . . ? C50 C51 C52 C53 0.4(7) . . . . ? C49 C48 C53 C52 0.7(7) . . . . ? N3 C48 C53 C52 -177.6(4) . . . . ? O13 C52 C53 C48 178.3(4) . . . . ? C51 C52 C53 C48 -0.8(6) . . . . ? C57 N4 C56 O14 1.6(7) . . . . ? C57 N4 C56 C43 -178.3(4) . . . . ? C44 C43 C56 O14 -156.2(4) . . . . ? C42 C43 C56 O14 22.1(6) . . . . ? C44 C43 C56 N4 23.8(6) . . . . ? C42 C43 C56 N4 -158.0(4) . . . . ? C56 N4 C57 C62 -19.3(7) . . . . ? C56 N4 C57 C58 160.9(4) . . . . ? C62 C57 C58 C59 1.4(6) . . . . ? N4 C57 C58 C59 -178.7(4) . . . . ? C63 O15 C59 C58 8.4(6) . . . . ? C63 O15 C59 C60 -171.6(4) . . . . ? C57 C58 C59 O15 178.8(4) . . . . ? C57 C58 C59 C60 -1.2(7) . . . . ? O15 C59 C60 C61 179.5(4) . . . . ? C58 C59 C60 C61 -0.5(7) . . . . ? C64 O16 C61 C60 -0.4(6) . . . . ? C64 O16 C61 C62 179.8(4) . . . . ? C59 C60 C61 O16 -177.7(4) . . . . ? C59 C60 C61 C62 2.0(7) . . . . ? C58 C57 C62 C61 0.0(7) . . . . ? N4 C57 C62 C61 -179.8(4) . . . . ? O16 C61 C62 C57 178.0(4) . . . . ? C60 C61 C62 C57 -1.7(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 N1 H1 O14 0.86 2.24 2.850(5) 127.4 . N1 H1 O10 0.86 2.64 3.232(5) 127.5 2_666 N2 H2 O3 0.86 2.09 2.940(5) 168.7 2_766 N3 H3A O6 0.86 2.08 2.845(5) 148.6 . N4 H4A O11 0.86 2.03 2.878(5) 169.5 2_656 _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.494 _refine_diff_density_min -0.549 _refine_diff_density_rms 0.158 data_03sot0155 _database_code_depnum_ccdc_archive 'CCDC 246438' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H24 N2 O5 S' _chemical_formula_weight 524.57 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.3919(17) _cell_length_b 4.9065(5) _cell_length_c 33.175(4) _cell_angle_alpha 90.00 _cell_angle_beta 102.202(2) _cell_angle_gamma 90.00 _cell_volume 2448.8(5) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 5654 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 29.50 _exptl_crystal_description Needle _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.423 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1096 _exptl_absorpt_coefficient_mu 0.179 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9651 _exptl_absorpt_correction_T_max 0.9964 _exptl_absorpt_process_details 'SORTAV (Blessing, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.69330 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'Daresbury SRS station 9.8' _diffrn_radiation_monochromator 'silicon 111' _diffrn_measurement_device_type 'Bruker SMART APEX2 CCD diffractometer' _diffrn_measurement_method 'fine-slice \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 5 _diffrn_reflns_number 16177 _diffrn_reflns_av_R_equivalents 0.0402 _diffrn_reflns_av_sigmaI/netI 0.0356 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 24.37 _reflns_number_total 4263 _reflns_number_gt 3444 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'CAMERON (Watkin, et al., 1993)' _computing_publication_material 'WINGX (Farrugia, 1998)' _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 phenyl groups is modelled disordered over two orientations. ; _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^)+(0.0354P)^2^+4.5299P] 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 SHELXL _refine_ls_extinction_coef 0.013(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4263 _refine_ls_number_parameters 364 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0738 _refine_ls_R_factor_gt 0.0586 _refine_ls_wR_factor_ref 0.1351 _refine_ls_wR_factor_gt 0.1294 _refine_ls_goodness_of_fit_ref 1.119 _refine_ls_restrained_S_all 1.119 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.29644(16) 0.4181(5) 0.06119(7) 0.0238(6) Uani 1 1 d . . . H1 H 0.3028 0.5835 0.0717 0.029 Uiso 1 1 calc R A 1 N2 N 0.37034(15) 0.5138(5) 0.26165(7) 0.0229(5) Uani 1 1 d . . . H2 H 0.3545 0.6810 0.2537 0.027 Uiso 1 1 calc R . . O1 O 0.10432(13) 0.4620(4) 0.04967(6) 0.0257(5) Uani 1 1 d . . . O2 O 0.09127(13) 1.0171(4) 0.18785(6) 0.0278(5) Uani 1 1 d . . . O3 O 0.25481(13) -0.0122(4) 0.07450(6) 0.0257(5) Uani 1 1 d . . . O4 O 0.36613(13) 0.0740(4) 0.23923(6) 0.0254(5) Uani 1 1 d . . . C1 C 0.16822(17) 0.5397(6) 0.11989(8) 0.0193(6) Uani 1 1 d . B . C2 C 0.10338(18) 0.5959(6) 0.08071(8) 0.0201(6) Uani 1 1 d . . . C3 C 0.03506(18) 0.8077(6) 0.08090(9) 0.0222(6) Uani 1 1 d . . . C4 C -0.0255(2) 0.8685(7) 0.04448(10) 0.0324(7) Uani 1 1 d . . . H4 H -0.0227 0.7746 0.0198 0.039 Uiso 1 1 calc R . . C5 C -0.0899(2) 1.0656(8) 0.04429(11) 0.0444(9) Uani 1 1 d . . . H5 H -0.1301 1.1099 0.0192 0.053 Uiso 1 1 calc R . . C6 C -0.0962(2) 1.1991(8) 0.08048(10) 0.0402(9) Uani 1 1 d . . . H6 H -0.1414 1.3313 0.0802 0.048 Uiso 1 1 calc R . . C7 C -0.03722(19) 1.1408(6) 0.11677(9) 0.0273(7) Uani 1 1 d . . . H7 H -0.0417 1.2327 0.1415 0.033 Uiso 1 1 calc R . . C8 C 0.02945(18) 0.9457(6) 0.11726(9) 0.0214(6) Uani 1 1 d . . . C9 C 0.09283(18) 0.8885(6) 0.15644(8) 0.0203(6) Uani 1 1 d . . . C10 C 0.16036(17) 0.6682(6) 0.15671(8) 0.0192(6) Uani 1 1 d . . . C11 C 0.21719(17) 0.6026(6) 0.19377(8) 0.0204(6) Uani 1 1 d . . . H11 H 0.2121 0.6943 0.2184 0.024 Uiso 1 1 calc R . . C12 C 0.28135(18) 0.4031(6) 0.19480(8) 0.0198(6) Uani 1 1 d . . . C13 C 0.29026(18) 0.2736(6) 0.15840(8) 0.0187(6) Uani 1 1 d . B . H13 H 0.3334 0.1341 0.1593 0.022 Uiso 1 1 calc R . . C14 C 0.23648(18) 0.3476(6) 0.12100(8) 0.0191(6) Uani 1 1 d . . . C15 C 0.26031(17) 0.2317(6) 0.08253(8) 0.0184(6) Uani 1 1 d . B . C16A C 0.3246(3) 0.3795(10) 0.02480(9) 0.0222(11) Uani 0.50 1 d PG B 1 C17A C 0.4129(2) 0.3869(9) 0.02129(10) 0.0271(13) Uani 0.50 1 d PG B 1 H17A H 0.4585 0.4217 0.0449 0.033 Uiso 0.50 1 calc PR B 1 C18A C 0.43468(19) 0.3433(10) -0.01679(12) 0.0320(15) Uani 0.50 1 d PG B 1 H18A H 0.4951 0.3483 -0.0192 0.038 Uiso 0.50 1 calc PR B 1 C19A C 0.3681(2) 0.2923(10) -0.05136(9) 0.0259(8) Uani 0.50 1 d PG B 1 H19A H 0.3829 0.2625 -0.0774 0.031 Uiso 0.50 1 calc PR B 1 C20A C 0.2797(2) 0.2849(9) -0.04785(10) 0.0261(13) Uani 0.50 1 d PG B 1 H20A H 0.2341 0.2501 -0.0715 0.031 Uiso 0.50 1 calc PR B 1 C21A C 0.25793(19) 0.3285(9) -0.00977(12) 0.0236(13) Uani 0.50 1 d PG B 1 H21A H 0.1975 0.3234 -0.0074 0.028 Uiso 0.50 1 calc PR B 1 C16B C 0.3107(3) 0.5900(6) -0.00581(11) 0.0222(11) Uani 0.50 1 d PG B 2 H16B H 0.2931 0.7630 0.0025 0.027 Uiso 0.50 1 calc PR B 2 C21B C 0.3140(3) 0.3662(8) 0.02015(9) 0.0158(15) Uani 0.50 1 d PG B 2 C17B C 0.3398(3) 0.1131(6) 0.00792(11) 0.0272(13) Uani 0.50 1 d PG B 2 H17B H 0.3420 -0.0398 0.0257 0.033 Uiso 0.50 1 calc PR B 2 C18B C 0.3623(3) 0.0839(6) -0.03028(12) 0.0316(15) Uani 0.50 1 d PG B 2 H18B H 0.3799 -0.0890 -0.0386 0.038 Uiso 0.50 1 calc PR B 2 C19B C 0.3591(3) 0.3077(8) -0.05624(9) 0.0259(8) Uani 0.50 1 d PG B 2 H19B H 0.3745 0.2878 -0.0823 0.031 Uiso 0.50 1 calc PR B 2 C20B C 0.3333(3) 0.5608(7) -0.04401(11) 0.0277(14) Uani 0.50 1 d PG B 2 H20B H 0.3310 0.7138 -0.0618 0.033 Uiso 0.50 1 calc PR B 2 C22 C 0.34305(18) 0.3146(6) 0.23410(8) 0.0199(6) Uani 1 1 d . . . C23 C 0.42193(18) 0.4828(6) 0.30215(9) 0.0218(6) Uani 1 1 d . . . C24 C 0.48723(19) 0.2844(6) 0.31283(9) 0.0265(7) Uani 1 1 d . . . H24 H 0.4989 0.1601 0.2927 0.032 Uiso 1 1 calc R . . C25 C 0.5350(2) 0.2698(7) 0.35303(9) 0.0302(7) Uani 1 1 d . . . H25 H 0.5796 0.1342 0.3603 0.036 Uiso 1 1 calc R . . C26 C 0.51903(19) 0.4481(6) 0.38273(9) 0.0277(7) Uani 1 1 d . . . H26 H 0.5518 0.4338 0.4103 0.033 Uiso 1 1 calc R . . C27 C 0.4550(2) 0.6479(7) 0.37208(10) 0.0338(7) Uani 1 1 d . . . H27 H 0.4444 0.7739 0.3922 0.041 Uiso 1 1 calc R . . C28 C 0.4062(2) 0.6642(7) 0.33178(9) 0.0318(7) Uani 1 1 d . . . H28 H 0.3618 0.8005 0.3245 0.038 Uiso 1 1 calc R . . S1 S 0.18688(5) 1.13995(18) 0.28837(2) 0.0327(3) Uani 1 1 d . . . O5 O 0.1826(3) 0.8408(6) 0.29087(10) 0.0885(13) Uani 1 1 d . . . C29 C 0.2178(3) 1.2605(8) 0.33996(10) 0.0425(9) Uani 1 1 d . . . H29A H 0.1771 1.1858 0.3562 0.064 Uiso 1 1 calc R . . H29B H 0.2146 1.4600 0.3401 0.064 Uiso 1 1 calc R . . H29C H 0.2786 1.2022 0.3520 0.064 Uiso 1 1 calc R . . C30 C 0.0785(2) 1.2644(9) 0.27764(12) 0.0503(11) Uani 1 1 d . . . H30A H 0.0509 1.2268 0.2488 0.075 Uiso 1 1 calc R . . H30B H 0.0794 1.4615 0.2825 0.075 Uiso 1 1 calc R . . H30C H 0.0443 1.1748 0.2956 0.075 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0322(13) 0.0157(12) 0.0271(13) -0.0024(10) 0.0147(11) -0.0017(10) N2 0.0283(13) 0.0137(12) 0.0246(13) 0.0021(10) 0.0010(10) 0.0015(10) O1 0.0276(11) 0.0260(12) 0.0233(11) -0.0029(9) 0.0048(8) 0.0013(9) O2 0.0286(11) 0.0277(12) 0.0284(11) -0.0052(9) 0.0089(9) 0.0044(9) O3 0.0317(11) 0.0179(11) 0.0296(11) -0.0028(9) 0.0108(9) -0.0004(9) O4 0.0347(12) 0.0157(11) 0.0259(11) -0.0004(8) 0.0065(9) 0.0015(9) C1 0.0201(14) 0.0153(14) 0.0246(14) 0.0004(11) 0.0093(11) -0.0034(11) C2 0.0205(14) 0.0190(15) 0.0221(14) -0.0013(12) 0.0076(11) -0.0057(12) C3 0.0207(14) 0.0203(15) 0.0260(15) 0.0031(12) 0.0056(12) -0.0036(12) C4 0.0340(17) 0.0341(19) 0.0282(16) 0.0020(14) 0.0042(13) 0.0035(15) C5 0.046(2) 0.048(2) 0.0345(19) 0.0019(17) -0.0024(16) 0.0216(18) C6 0.0361(19) 0.043(2) 0.0400(19) 0.0026(16) 0.0034(15) 0.0200(16) C7 0.0272(15) 0.0237(16) 0.0327(16) -0.0003(13) 0.0104(13) 0.0042(13) C8 0.0188(14) 0.0191(15) 0.0280(15) 0.0013(12) 0.0086(11) -0.0019(11) C9 0.0218(14) 0.0160(14) 0.0252(15) -0.0004(12) 0.0101(11) -0.0018(12) C10 0.0184(13) 0.0175(15) 0.0233(14) -0.0017(12) 0.0075(11) -0.0021(11) C11 0.0221(14) 0.0170(14) 0.0236(14) -0.0008(12) 0.0083(11) -0.0034(12) C12 0.0226(14) 0.0145(14) 0.0237(14) 0.0016(11) 0.0077(11) -0.0034(11) C13 0.0219(14) 0.0131(14) 0.0227(14) -0.0005(11) 0.0084(11) -0.0012(11) C14 0.0229(14) 0.0135(14) 0.0226(14) -0.0022(11) 0.0084(11) -0.0039(11) C15 0.0186(13) 0.0154(15) 0.0203(14) 0.0017(11) 0.0020(11) 0.0027(11) C16A 0.026(3) 0.014(3) 0.028(2) 0.001(2) 0.007(2) 0.002(2) C17A 0.023(3) 0.029(3) 0.028(3) -0.001(3) 0.004(2) 0.001(3) C18A 0.028(3) 0.037(4) 0.036(3) 0.003(3) 0.017(3) 0.004(3) C19A 0.0318(18) 0.0252(17) 0.0234(17) -0.0012(14) 0.0120(15) 0.0000(14) C20A 0.033(3) 0.023(3) 0.021(3) -0.002(2) 0.002(2) 0.001(3) C21A 0.026(3) 0.025(3) 0.022(3) 0.002(2) 0.009(3) 0.002(3) C16B 0.026(3) 0.014(3) 0.028(2) 0.001(2) 0.007(2) 0.002(2) C21B 0.016(3) 0.020(4) 0.014(3) -0.002(3) 0.008(3) -0.003(3) C17B 0.040(3) 0.017(3) 0.026(3) 0.001(2) 0.010(3) -0.005(3) C18B 0.047(4) 0.023(3) 0.028(3) -0.003(3) 0.016(3) 0.007(3) C19B 0.0318(18) 0.0252(17) 0.0234(17) -0.0012(14) 0.0120(15) 0.0000(14) C20B 0.034(3) 0.027(3) 0.024(3) 0.007(3) 0.010(3) 0.008(3) C22 0.0235(14) 0.0173(15) 0.0218(14) 0.0010(11) 0.0109(12) 0.0007(12) C23 0.0222(14) 0.0189(15) 0.0244(15) 0.0020(12) 0.0057(11) -0.0039(12) C24 0.0250(15) 0.0262(16) 0.0295(16) -0.0016(13) 0.0083(13) 0.0039(13) C25 0.0245(15) 0.0322(18) 0.0327(17) 0.0022(14) 0.0029(13) 0.0048(14) C26 0.0256(15) 0.0314(18) 0.0253(15) 0.0070(13) 0.0035(12) -0.0050(13) C27 0.0355(17) 0.0374(19) 0.0281(16) -0.0064(15) 0.0062(13) 0.0016(15) C28 0.0321(17) 0.0296(18) 0.0314(17) -0.0049(14) 0.0017(13) 0.0078(14) S1 0.0329(4) 0.0334(5) 0.0328(5) -0.0024(4) 0.0089(3) 0.0094(4) O5 0.155(3) 0.0279(16) 0.061(2) -0.0047(14) -0.026(2) 0.0275(19) C29 0.055(2) 0.033(2) 0.0369(19) -0.0005(16) 0.0028(17) 0.0038(17) C30 0.0339(19) 0.056(3) 0.057(2) -0.031(2) 0.0017(17) 0.0088(18) _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 N1 C15 1.347(4) . ? N1 C16A 1.379(3) . ? N1 C21B 1.465(3) . ? N2 C22 1.344(4) . ? N2 C23 1.417(4) . ? O1 C2 1.224(3) . ? O2 C9 1.223(3) . ? O3 C15 1.225(3) . ? O4 C22 1.234(3) . ? C1 C10 1.402(4) . ? C1 C14 1.406(4) . ? C1 C2 1.488(4) . ? C2 C3 1.479(4) . ? C3 C4 1.394(4) . ? C3 C8 1.402(4) . ? C4 C5 1.384(5) . ? C5 C6 1.389(5) . ? C6 C7 1.376(4) . ? C7 C8 1.401(4) . ? C8 C9 1.478(4) . ? C9 C10 1.498(4) . ? C10 C11 1.388(4) . ? C11 C12 1.386(4) . ? C12 C13 1.397(4) . ? C12 C22 1.506(4) . ? C13 C14 1.386(4) . ? C14 C15 1.511(4) . ? C16A C17A 1.3900 . ? C16A C21A 1.3900 . ? C17A C18A 1.3900 . ? C18A C19A 1.3900 . ? C19A C20A 1.3900 . ? C20A C21A 1.3900 . ? C16B C21B 1.3900 . ? C16B C20B 1.3900 . ? C21B C17B 1.3900 . ? C17B C18B 1.3900 . ? C18B C19B 1.3900 . ? C19B C20B 1.3900 . ? C23 C28 1.385(4) . ? C23 C24 1.390(4) . ? C24 C25 1.382(4) . ? C25 C26 1.378(4) . ? C26 C27 1.382(4) . ? C27 C28 1.391(4) . ? S1 O5 1.472(3) . ? S1 C30 1.741(3) . ? S1 C29 1.778(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C15 N1 C16A 127.4(3) . . ? C15 N1 C21B 123.2(3) . . ? C22 N2 C23 126.8(2) . . ? C10 C1 C14 118.7(2) . . ? C10 C1 C2 120.8(2) . . ? C14 C1 C2 120.4(2) . . ? O1 C2 C3 121.0(3) . . ? O1 C2 C1 120.7(3) . . ? C3 C2 C1 118.2(2) . . ? C4 C3 C8 119.4(3) . . ? C4 C3 C2 119.5(3) . . ? C8 C3 C2 121.1(3) . . ? C5 C4 C3 120.1(3) . . ? C4 C5 C6 120.4(3) . . ? C7 C6 C5 120.3(3) . . ? C6 C7 C8 119.9(3) . . ? C7 C8 C3 119.9(3) . . ? C7 C8 C9 119.1(3) . . ? C3 C8 C9 121.1(2) . . ? O2 C9 C8 121.6(3) . . ? O2 C9 C10 120.4(3) . . ? C8 C9 C10 118.1(2) . . ? C11 C10 C1 120.9(3) . . ? C11 C10 C9 118.6(2) . . ? C1 C10 C9 120.4(2) . . ? C12 C11 C10 119.9(3) . . ? C11 C12 C13 120.0(3) . . ? C11 C12 C22 122.7(2) . . ? C13 C12 C22 117.3(2) . . ? C14 C13 C12 120.4(3) . . ? C13 C14 C1 120.0(2) . . ? C13 C14 C15 116.9(2) . . ? C1 C14 C15 122.9(2) . . ? O3 C15 N1 124.5(3) . . ? O3 C15 C14 122.2(2) . . ? N1 C15 C14 112.9(2) . . ? N1 C16A C17A 124.3(3) . . ? N1 C16A C21A 115.7(3) . . ? C17A C16A C21A 120.0 . . ? C18A C17A C16A 120.0 . . ? C17A C18A C19A 120.0 . . ? C20A C19A C18A 120.0 . . ? C19A C20A C21A 120.0 . . ? C20A C21A C16A 120.0 . . ? C21B C16B C20B 120.0 . . ? C16B C21B C17B 120.0 . . ? C16B C21B N1 116.7(3) . . ? C17B C21B N1 123.1(3) . . ? C18B C17B C21B 120.0 . . ? C17B C18B C19B 120.0 . . ? C18B C19B C20B 120.0 . . ? C19B C20B C16B 120.0 . . ? O4 C22 N2 124.2(3) . . ? O4 C22 C12 120.4(3) . . ? N2 C22 C12 115.4(2) . . ? C28 C23 C24 119.6(3) . . ? C28 C23 N2 117.2(3) . . ? C24 C23 N2 123.2(3) . . ? C25 C24 C23 119.4(3) . . ? C26 C25 C24 121.2(3) . . ? C25 C26 C27 119.5(3) . . ? C26 C27 C28 119.9(3) . . ? C23 C28 C27 120.3(3) . . ? O5 S1 C30 108.0(2) . . ? O5 S1 C29 106.48(18) . . ? C30 S1 C29 97.47(17) . . ? 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 N1 H1 O3 0.88 2.13 2.922(3) 150.1 1_565 N2 H2 O4 0.88 2.00 2.845(3) 159.3 1_565 _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 24.37 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.422 _refine_diff_density_min -0.472 _refine_diff_density_rms 0.056 #===END data_03sot0169 _database_code_depnum_ccdc_archive 'CCDC 246439' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H50 Cl4 F N3 O4' _chemical_formula_weight 845.67 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' F F 0.0171 0.0103 '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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 18.133(5) _cell_length_b 24.621(5) _cell_length_c 37.774(5) _cell_angle_alpha 90.000 _cell_angle_beta 90.000 _cell_angle_gamma 90.000 _cell_volume 16864(6) _cell_formula_units_Z 16 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 134527 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 26.02 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.332 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 7104 _exptl_absorpt_coefficient_mu 0.331 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9307 _exptl_absorpt_correction_T_max 0.9901 _exptl_absorpt_process_details 'SORTAV (Blessing, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker Nonius FR591 Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Nonius Kappa CCD Area detector' _diffrn_measurement_method '\f and \w scans to fill the asymmetric unit' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 95521 _diffrn_reflns_av_R_equivalents 0.1075 _diffrn_reflns_av_sigmaI/netI 0.0857 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -44 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 25.03 _reflns_number_total 14874 _reflns_number_gt 8862 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1999)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'CAMERON (Watkin, et al., 1993)' _computing_publication_material 'WINGX (Farrugia, 1998)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The absolute value of parameter shift to su ratio is slightly high due to disorder, extensive refienement would not further converge the refinement. One arm of the TBA is modelled as disordered over two conformations, and one of the chloro phenyl groups is disordered over 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^)+(0.1227P)^2^+62.1203P] 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 SHELXL _refine_ls_extinction_coef 0.0029(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 14874 _refine_ls_number_parameters 942 _refine_ls_number_restraints 26 _refine_ls_R_factor_all 0.1695 _refine_ls_R_factor_gt 0.1082 _refine_ls_wR_factor_ref 0.2893 _refine_ls_wR_factor_gt 0.2511 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.116 _refine_ls_shift/su_mean 0.002 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 F1 F 0.6122(2) 0.26762(15) 0.11320(10) 0.0562(10) Uani 1 1 d . . . F2 F 0.31921(18) 0.23618(13) 0.11542(9) 0.0406(8) Uani 1 1 d . . . Cl3 Cl 0.14352(12) 0.17451(8) 0.20761(5) 0.0714(6) Uani 1 1 d . . . Cl4 Cl 0.17763(10) 0.36529(7) 0.27407(4) 0.0556(5) Uani 1 1 d . . . O1 O 0.5842(3) 0.36978(17) 0.02610(12) 0.0506(12) Uani 1 1 d . . . O2 O 0.4604(3) 0.53411(18) 0.09692(15) 0.0685(16) Uani 1 1 d . . . O3 O 0.4489(2) 0.29823(18) 0.01872(11) 0.0464(11) Uani 1 1 d . . . O4 O 0.3207(3) 0.41069(16) 0.16821(12) 0.0499(12) Uani 1 1 d . . . N1 N 0.5272(3) 0.25974(18) 0.05891(14) 0.0371(12) Uani 1 1 d . . . H1 H 0.5479 0.2671 0.0794 0.045 Uiso 1 1 calc R A 1 N2 N 0.3107(3) 0.32009(19) 0.15759(12) 0.0360(12) Uani 1 1 d . . . H2 H 0.3252 0.2938 0.1434 0.043 Uiso 1 1 calc R . . C1 C 0.4928(3) 0.3973(2) 0.06647(15) 0.0317(13) Uani 1 1 d . . . C2 C 0.5514(3) 0.4079(2) 0.03975(16) 0.0361(14) Uani 1 1 d . . . C3 C 0.5701(3) 0.4647(2) 0.03173(16) 0.0364(14) Uani 1 1 d . . . C4 C 0.6198(4) 0.4756(3) 0.00468(18) 0.0458(16) Uani 1 1 d . . . H4 H 0.6424 0.4465 -0.0078 0.055 Uiso 1 1 calc R . . C5 C 0.6363(4) 0.5284(3) -0.00413(19) 0.0528(18) Uani 1 1 d . . . H5 H 0.6699 0.5354 -0.0229 0.063 Uiso 1 1 calc R . . C6 C 0.6048(4) 0.5713(3) 0.01387(18) 0.0495(17) Uani 1 1 d . . . H6 H 0.6161 0.6077 0.0074 0.059 Uiso 1 1 calc R . . C7 C 0.5567(4) 0.5609(3) 0.04126(18) 0.0470(16) Uani 1 1 d . . . H7 H 0.5357 0.5903 0.0540 0.056 Uiso 1 1 calc R . . C8 C 0.5385(3) 0.5080(2) 0.05046(16) 0.0402(15) Uani 1 1 d . . . C9 C 0.4869(4) 0.4970(2) 0.07983(17) 0.0421(15) Uani 1 1 d . . . C10 C 0.4649(3) 0.4398(2) 0.08695(15) 0.0344(13) Uani 1 1 d . . . C11 C 0.4143(3) 0.4293(2) 0.11389(15) 0.0349(14) Uani 1 1 d . . . H11 H 0.3959 0.4586 0.1277 0.042 Uiso 1 1 calc R . . C12 C 0.3904(3) 0.3770(2) 0.12078(14) 0.0309(13) Uani 1 1 d . . . C13 C 0.4165(3) 0.3348(2) 0.09943(14) 0.0290(12) Uani 1 1 d . . . H13 H 0.3997 0.2988 0.1036 0.035 Uiso 1 1 calc R . . C14 C 0.4666(3) 0.3446(2) 0.07223(15) 0.0315(13) Uani 1 1 d . . . C15 C 0.4822(3) 0.2987(2) 0.04727(16) 0.0353(14) Uani 1 1 d . . . Cl1A Cl 0.5224(2) 0.11781(16) -0.04032(13) 0.0751(8) Uani 0.50 1 d PD B 1 Cl2A Cl 0.6744(2) 0.08892(15) 0.07920(14) 0.0751(8) Uani 0.50 1 d PD B 1 C16A C 0.5478(7) 0.2099(3) 0.0450(2) 0.0490(12) Uani 0.50 1 d PGD B 1 C17A C 0.5929(6) 0.1773(3) 0.0658(2) 0.0490(12) Uani 0.50 1 d PGD B 1 H17A H 0.6092 0.1898 0.0883 0.059 Uiso 0.50 1 calc PR B 1 C18A C 0.6141(5) 0.1263(3) 0.0538(2) 0.0490(12) Uani 0.50 1 d PGD B 1 C19A C 0.5903(5) 0.1079(2) 0.0209(2) 0.0490(12) Uani 0.50 1 d PGD B 1 H19A H 0.6048 0.0730 0.0127 0.059 Uiso 0.50 1 calc PR B 1 C20A C 0.5452(5) 0.1405(3) 0.00008(18) 0.0490(12) Uani 0.50 1 d PGD B 1 C21A C 0.5239(6) 0.1915(3) 0.0121(2) 0.0490(12) Uani 0.50 1 d PGD B 1 H21A H 0.4931 0.2138 -0.0021 0.059 Uiso 0.50 1 calc PR B 1 Cl1B Cl 0.5036(2) 0.14650(16) -0.05598(12) 0.0751(8) Uani 0.50 1 d PD B 2 Cl2B Cl 0.6630(2) 0.08089(15) 0.05478(14) 0.0751(8) Uani 0.50 1 d PD B 2 C16B C 0.5411(7) 0.2124(3) 0.0382(2) 0.0490(12) Uani 0.50 1 d PGD B 2 C17B C 0.5837(6) 0.1725(3) 0.05425(19) 0.0490(12) Uani 0.50 1 d PGD B 2 H17B H 0.6014 0.1777 0.0777 0.059 Uiso 0.50 1 calc PR B 2 C18B C 0.6004(5) 0.1250(2) 0.0361(2) 0.0490(12) Uani 0.50 1 d PGD B 2 C19B C 0.5745(5) 0.1174(2) 0.0018(2) 0.0490(12) Uani 0.50 1 d PGD B 2 H19B H 0.5859 0.0849 -0.0106 0.059 Uiso 0.50 1 calc PR B 2 C20B C 0.5318(5) 0.1573(3) -0.01429(17) 0.0490(12) Uani 0.50 1 d PGD B 2 C21B C 0.5151(6) 0.2048(3) 0.0039(2) 0.0490(12) Uani 0.50 1 d PGD B 2 H21B H 0.4860 0.2321 -0.0071 0.059 Uiso 0.50 1 calc PR B 2 C22 C 0.3380(3) 0.3706(2) 0.15119(15) 0.0357(14) Uani 1 1 d . . . C23 C 0.2614(2) 0.30630(14) 0.18492(9) 0.0365(14) Uani 1 1 d G . . C24 C 0.2289(2) 0.25525(14) 0.18279(9) 0.0428(15) Uani 1 1 d G . . H24 H 0.2399 0.2320 0.1634 0.051 Uiso 1 1 calc R . . C25 C 0.1804(2) 0.23816(13) 0.20902(11) 0.0484(17) Uani 1 1 d G . . C26 C 0.1644(2) 0.27212(16) 0.23739(10) 0.0500(17) Uani 1 1 d G . . H26 H 0.1313 0.2604 0.2553 0.060 Uiso 1 1 calc R . . C27 C 0.1968(2) 0.32317(15) 0.23953(9) 0.0442(16) Uani 1 1 d G . . C28 C 0.2453(2) 0.34026(12) 0.21329(10) 0.0374(14) Uani 1 1 d G . . H28 H 0.2675 0.3752 0.2147 0.045 Uiso 1 1 calc R . . Cl5 Cl 0.52042(11) -0.00966(7) 0.08746(5) 0.0621(5) Uani 1 1 d . . . Cl6 Cl 0.22959(10) 0.03386(7) 0.08755(5) 0.0568(5) Uani 1 1 d . . . Cl7 Cl 0.83510(12) 0.38005(8) 0.08605(5) 0.0709(6) Uani 1 1 d . . . Cl8 Cl 0.67101(13) 0.55438(8) 0.11816(6) 0.0729(6) Uani 1 1 d . . . O5 O 0.3562(3) 0.14998(17) 0.21553(12) 0.0599(14) Uani 1 1 d . . . O6 O 0.3818(3) 0.3431(2) 0.28082(13) 0.0694(15) Uani 1 1 d . . . O7 O 0.5028(3) 0.13915(18) 0.17826(12) 0.0612(14) Uani 1 1 d . . . O8 O 0.5302(3) 0.41391(16) 0.18565(12) 0.0502(12) Uani 1 1 d . . . N3 N 0.4141(3) 0.16724(18) 0.13888(12) 0.0392(12) Uani 1 1 d . . . H3 H 0.3907 0.1961 0.1309 0.047 Uiso 1 1 calc R . . N4 N 0.5876(3) 0.3584(2) 0.14607(14) 0.0457(13) Uani 1 1 d . . . H4A H 0.5871 0.3255 0.1369 0.055 Uiso 1 1 calc R . . C29 C 0.4126(4) 0.2371(2) 0.21621(16) 0.0432(16) Uani 1 1 d . . . C30 C 0.3635(4) 0.1939(3) 0.23082(18) 0.0517(18) Uani 1 1 d . . . C31 C 0.3223(4) 0.2057(3) 0.26364(17) 0.0538(18) Uani 1 1 d . . . C32 C 0.2739(5) 0.1668(3) 0.2771(2) 0.070(2) Uani 1 1 d . . . H32 H 0.2684 0.1330 0.2653 0.084 Uiso 1 1 calc R . . C33 C 0.2342(6) 0.1770(3) 0.3075(2) 0.077(3) Uani 1 1 d . . . H33 H 0.2021 0.1500 0.3167 0.092 Uiso 1 1 calc R . . C34 C 0.2405(6) 0.2262(3) 0.3247(2) 0.074(2) Uani 1 1 d . . . H34 H 0.2126 0.2331 0.3455 0.089 Uiso 1 1 calc R . . C35 C 0.2879(5) 0.2657(3) 0.31158(18) 0.062(2) Uani 1 1 d . . . H35 H 0.2925 0.2996 0.3235 0.074 Uiso 1 1 calc R . . C36 C 0.3287(4) 0.2558(3) 0.28099(18) 0.0529(18) Uani 1 1 d . . . C37 C 0.3757(4) 0.2991(3) 0.26634(19) 0.0554(19) Uani 1 1 d . . . C38 C 0.4163(4) 0.2878(2) 0.23268(17) 0.0467(17) Uani 1 1 d . . . C39 C 0.4574(4) 0.3292(3) 0.21770(17) 0.0458(16) Uani 1 1 d . . . H39 H 0.4583 0.3638 0.2287 0.055 Uiso 1 1 calc R . . C40 C 0.4972(4) 0.3210(2) 0.18706(17) 0.0425(16) Uani 1 1 d . . . C41 C 0.4964(4) 0.2697(2) 0.17106(17) 0.0448(16) Uani 1 1 d . . . H41 H 0.5253 0.2633 0.1505 0.054 Uiso 1 1 calc R . . C42 C 0.4535(4) 0.2280(2) 0.18523(17) 0.0446(16) Uani 1 1 d . . . C43 C 0.4586(4) 0.1730(3) 0.16766(17) 0.0469(16) Uani 1 1 d . . . C44 C 0.4037(2) 0.11744(12) 0.12119(10) 0.0386(15) Uani 1 1 d G . . C45 C 0.33185(19) 0.10221(14) 0.11305(11) 0.0407(15) Uani 1 1 d G . . H45 H 0.2920 0.1258 0.1185 0.049 Uiso 1 1 calc R . . C46 C 0.31832(18) 0.05239(16) 0.09701(11) 0.0442(16) Uani 1 1 d G . . C47 C 0.3766(2) 0.01780(12) 0.08910(10) 0.0480(17) Uani 1 1 d G . . H47 H 0.3674 -0.0162 0.0781 0.058 Uiso 1 1 calc R . . C48 C 0.4485(2) 0.03303(14) 0.09723(11) 0.0424(16) Uani 1 1 d G . . C49 C 0.46200(17) 0.08285(15) 0.11328(11) 0.0409(15) Uani 1 1 d G . . H49 H 0.5111 0.0933 0.1188 0.049 Uiso 1 1 calc R . . C50 C 0.5394(4) 0.3688(3) 0.17261(18) 0.0452(16) Uani 1 1 d . . . C51 C 0.6387(2) 0.39592(16) 0.13199(11) 0.0483(17) Uani 1 1 d G . . C52 C 0.6288(2) 0.45190(17) 0.13214(12) 0.0509(17) Uani 1 1 d G . . H52 H 0.5855 0.4672 0.1422 0.061 Uiso 1 1 calc R . . C53 C 0.6823(3) 0.48555(12) 0.11754(12) 0.0577(19) Uani 1 1 d G . . C54 C 0.7457(2) 0.46322(17) 0.10280(12) 0.060(2) Uani 1 1 d G . . H54 H 0.7823 0.4862 0.0928 0.072 Uiso 1 1 calc R . . C55 C 0.7555(2) 0.40723(18) 0.10266(11) 0.0553(18) Uani 1 1 d G . . C56 C 0.7020(3) 0.37358(13) 0.11725(12) 0.0484(17) Uani 1 1 d G . . H56 H 0.7087 0.3353 0.1172 0.058 Uiso 1 1 calc R . . N5 N 0.4453(3) -0.01519(19) 0.20877(13) 0.0387(12) Uani 1 1 d . . . C57 C 0.3805(3) 0.0155(2) 0.19228(16) 0.0382(14) Uani 1 1 d . C . H57A H 0.3922 0.0548 0.1927 0.046 Uiso 1 1 calc R . . H57B H 0.3766 0.0046 0.1671 0.046 Uiso 1 1 calc R . . C58 C 0.3059(3) 0.0077(3) 0.20928(17) 0.0444(16) Uani 1 1 d . . . H58A H 0.2954 -0.0316 0.2115 0.053 Uiso 1 1 calc R C . H58B H 0.3063 0.0237 0.2333 0.053 Uiso 1 1 calc R . . C59 C 0.2466(3) 0.0343(3) 0.18756(17) 0.0433(15) Uani 1 1 d . C . H59A H 0.2448 0.0166 0.1640 0.052 Uiso 1 1 calc R . . H59B H 0.2596 0.0729 0.1839 0.052 Uiso 1 1 calc R . . C60 C 0.1706(4) 0.0312(3) 0.20429(19) 0.0510(17) Uani 1 1 d . . . H60A H 0.1573 -0.0069 0.2082 0.076 Uiso 1 1 calc R C . H60B H 0.1344 0.0481 0.1885 0.076 Uiso 1 1 calc R . . H60C H 0.1710 0.0505 0.2270 0.076 Uiso 1 1 calc R . . C61 C 0.4476(4) -0.0070(3) 0.24832(16) 0.0445(16) Uani 1 1 d . C . H61A H 0.4010 -0.0209 0.2585 0.053 Uiso 1 1 calc R . . H61B H 0.4883 -0.0293 0.2581 0.053 Uiso 1 1 calc R . . C62 C 0.4581(4) 0.0506(3) 0.26051(17) 0.0497(17) Uani 1 1 d . . . H62A H 0.4217 0.0744 0.2487 0.060 Uiso 1 1 calc R C . H62B H 0.5082 0.0632 0.2540 0.060 Uiso 1 1 calc R . . C63 C 0.4481(4) 0.0536(3) 0.30044(18) 0.0587(19) Uani 1 1 d . C . H63A H 0.3981 0.0406 0.3066 0.070 Uiso 1 1 calc R . . H63B H 0.4841 0.0290 0.3119 0.070 Uiso 1 1 calc R . . C64 C 0.4584(5) 0.1105(3) 0.3150(2) 0.073(2) Uani 1 1 d . . . H64A H 0.5090 0.1226 0.3104 0.110 Uiso 1 1 calc R C . H64B H 0.4493 0.1104 0.3405 0.110 Uiso 1 1 calc R . . H64C H 0.4236 0.1352 0.3034 0.110 Uiso 1 1 calc R . . C65A C 0.439(2) -0.0794(8) 0.2005(5) 0.0606(15) Uani 0.45 1 d PD C 3 H65A H 0.4852 -0.0974 0.2076 0.073 Uiso 0.45 1 calc PR C 3 H65B H 0.3985 -0.0948 0.2150 0.073 Uiso 0.45 1 calc PR C 3 C66A C 0.4235(10) -0.0926(4) 0.1613(5) 0.0606(15) Uani 0.45 1 d PD C 3 H66A H 0.3745 -0.0783 0.1545 0.073 Uiso 0.45 1 calc PR C 3 H66B H 0.4610 -0.0746 0.1463 0.073 Uiso 0.45 1 calc PR C 3 C67A C 0.4257(7) -0.1543(5) 0.1548(5) 0.0606(15) Uani 0.45 1 d PD C 3 H67A H 0.3848 -0.1716 0.1680 0.073 Uiso 0.45 1 calc PR C 3 H67B H 0.4176 -0.1613 0.1293 0.073 Uiso 0.45 1 calc PR C 3 C68A C 0.4989(7) -0.1808(6) 0.1661(5) 0.0606(15) Uani 0.45 1 d PD C 3 H68A H 0.5395 -0.1652 0.1523 0.091 Uiso 0.45 1 calc PR C 3 H68B H 0.4964 -0.2201 0.1618 0.091 Uiso 0.45 1 calc PR C 3 H68C H 0.5073 -0.1741 0.1913 0.091 Uiso 0.45 1 calc PR C 3 C65B C 0.4362(18) -0.0730(6) 0.2044(5) 0.0606(15) Uani 0.55 1 d PD C 4 H65C H 0.3850 -0.0826 0.2110 0.073 Uiso 0.55 1 calc PR C 4 H65D H 0.4695 -0.0917 0.2212 0.073 Uiso 0.55 1 calc PR C 4 C66B C 0.4514(8) -0.0949(4) 0.1669(4) 0.0606(15) Uani 0.55 1 d PD C 4 H66C H 0.5025 -0.0858 0.1599 0.073 Uiso 0.55 1 calc PR C 4 H66D H 0.4174 -0.0774 0.1499 0.073 Uiso 0.55 1 calc PR C 4 C67B C 0.4408(8) -0.1569(4) 0.1655(3) 0.0606(15) Uani 0.55 1 d PD C 4 H67C H 0.4540 -0.1725 0.1888 0.073 Uiso 0.55 1 calc PR C 4 H67D H 0.3880 -0.1649 0.1612 0.073 Uiso 0.55 1 calc PR C 4 C68B C 0.4874(7) -0.1847(5) 0.1367(3) 0.0606(15) Uani 0.55 1 d PD C 4 H68D H 0.4671 -0.1758 0.1133 0.091 Uiso 0.55 1 calc PR C 4 H68E H 0.4863 -0.2241 0.1402 0.091 Uiso 0.55 1 calc PR C 4 H68F H 0.5384 -0.1717 0.1382 0.091 Uiso 0.55 1 calc PR C 4 C69 C 0.5146(3) 0.0064(3) 0.19133(17) 0.0418(15) Uani 1 1 d . C . H69A H 0.5099 0.0013 0.1654 0.050 Uiso 1 1 calc R . . H69B H 0.5174 0.0460 0.1958 0.050 Uiso 1 1 calc R . . C70 C 0.5859(4) -0.0191(3) 0.20318(19) 0.0493(17) Uani 1 1 d . . . H70A H 0.5872 -0.0576 0.1957 0.059 Uiso 1 1 calc R C . H70B H 0.5891 -0.0181 0.2293 0.059 Uiso 1 1 calc R . . C71 C 0.6512(4) 0.0108(3) 0.1874(2) 0.064(2) Uani 1 1 d . C . H71A H 0.6457 0.0118 0.1613 0.076 Uiso 1 1 calc R . . H71B H 0.6511 0.0487 0.1961 0.076 Uiso 1 1 calc R . . C72 C 0.7234(4) -0.0149(4) 0.1964(2) 0.081(3) Uani 1 1 d . . . H72A H 0.7276 -0.0186 0.2221 0.121 Uiso 1 1 calc R C . H72B H 0.7637 0.0079 0.1875 0.121 Uiso 1 1 calc R . . H72C H 0.7263 -0.0509 0.1854 0.121 Uiso 1 1 calc R . . N6 N 0.2491(3) 0.23128(19) 0.01652(13) 0.0359(11) Uani 1 1 d . . . C73 C 0.1733(3) 0.2125(3) 0.02818(16) 0.0398(15) Uani 1 1 d . . . H73A H 0.1370 0.2407 0.0216 0.048 Uiso 1 1 calc R . . H73B H 0.1606 0.1792 0.0148 0.048 Uiso 1 1 calc R . . C74 C 0.1649(4) 0.2006(3) 0.06712(17) 0.0457(16) Uani 1 1 d . . . H74A H 0.2016 0.1729 0.0744 0.055 Uiso 1 1 calc R . . H74B H 0.1743 0.2340 0.0809 0.055 Uiso 1 1 calc R . . C75 C 0.0887(4) 0.1801(4) 0.0749(2) 0.075(2) Uani 1 1 d . . . H75A H 0.0794 0.1470 0.0607 0.090 Uiso 1 1 calc R . . H75B H 0.0524 0.2080 0.0675 0.090 Uiso 1 1 calc R . . C76 C 0.0772(4) 0.1671(4) 0.1134(2) 0.072(2) Uani 1 1 d . . . H76A H 0.1141 0.1405 0.1211 0.108 Uiso 1 1 calc R . . H76B H 0.0277 0.1521 0.1168 0.108 Uiso 1 1 calc R . . H76C H 0.0824 0.2004 0.1275 0.108 Uiso 1 1 calc R . . C77 C 0.2451(3) 0.2409(3) -0.02284(16) 0.0412(15) Uani 1 1 d . . . H77A H 0.2074 0.2692 -0.0273 0.049 Uiso 1 1 calc R . . H77B H 0.2276 0.2071 -0.0342 0.049 Uiso 1 1 calc R . . C78 C 0.3157(4) 0.2580(3) -0.04084(16) 0.0437(16) Uani 1 1 d . . . H78A H 0.3500 0.2268 -0.0418 0.052 Uiso 1 1 calc R . . H78B H 0.3394 0.2873 -0.0269 0.052 Uiso 1 1 calc R . . C79 C 0.3007(4) 0.2781(3) -0.07814(17) 0.0509(17) Uani 1 1 d . . . H79A H 0.2747 0.2493 -0.0915 0.061 Uiso 1 1 calc R . . H79B H 0.2678 0.3102 -0.0770 0.061 Uiso 1 1 calc R . . C80 C 0.3701(4) 0.2932(3) -0.09753(19) 0.060(2) Uani 1 1 d . . . H80A H 0.3968 0.3210 -0.0840 0.090 Uiso 1 1 calc R . . H80B H 0.3575 0.3076 -0.1210 0.090 Uiso 1 1 calc R . . H80C H 0.4013 0.2610 -0.1002 0.090 Uiso 1 1 calc R . . C81 C 0.3065(3) 0.1884(2) 0.02517(17) 0.0375(14) Uani 1 1 d . . . H81A H 0.3543 0.2001 0.0151 0.045 Uiso 1 1 calc R . . H81B H 0.3123 0.1868 0.0512 0.045 Uiso 1 1 calc R . . C82 C 0.2898(4) 0.1318(2) 0.01182(17) 0.0443(16) Uani 1 1 d . . . H82A H 0.2689 0.1339 -0.0123 0.053 Uiso 1 1 calc R . . H82B H 0.2529 0.1143 0.0274 0.053 Uiso 1 1 calc R . . C83 C 0.3599(4) 0.0983(2) 0.01130(18) 0.0463(16) Uani 1 1 d . . . H83A H 0.3821 0.0985 0.0352 0.056 Uiso 1 1 calc R . . H83B H 0.3955 0.1153 -0.0052 0.056 Uiso 1 1 calc R . . C84 C 0.3470(4) 0.0399(3) 0.0000(2) 0.0581(19) Uani 1 1 d . . . H84A H 0.3155 0.0218 0.0175 0.087 Uiso 1 1 calc R . . H84B H 0.3944 0.0210 -0.0015 0.087 Uiso 1 1 calc R . . H84C H 0.3227 0.0394 -0.0231 0.087 Uiso 1 1 calc R . . C85 C 0.2725(3) 0.2821(2) 0.03604(15) 0.0351(14) Uani 1 1 d . . . H85A H 0.2689 0.2753 0.0618 0.042 Uiso 1 1 calc R . . H85B H 0.3249 0.2895 0.0305 0.042 Uiso 1 1 calc R . . C86 C 0.2277(4) 0.3321(2) 0.02722(18) 0.0445(16) Uani 1 1 d . . . H86A H 0.1746 0.3228 0.0276 0.053 Uiso 1 1 calc R . . H86B H 0.2401 0.3444 0.0030 0.053 Uiso 1 1 calc R . . C87 C 0.2420(4) 0.3781(2) 0.05320(17) 0.0459(16) Uani 1 1 d . . . H87A H 0.2958 0.3815 0.0569 0.055 Uiso 1 1 calc R . . H87B H 0.2244 0.4125 0.0426 0.055 Uiso 1 1 calc R . . C88 C 0.2056(4) 0.3710(3) 0.08844(19) 0.0553(19) Uani 1 1 d . . . H88A H 0.1523 0.3671 0.0851 0.083 Uiso 1 1 calc R . . H88B H 0.2156 0.4028 0.1033 0.083 Uiso 1 1 calc R . . H88C H 0.2252 0.3384 0.1000 0.083 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 F1 0.064(2) 0.050(2) 0.054(2) -0.0062(18) -0.012(2) 0.0141(19) F2 0.048(2) 0.0338(18) 0.0403(19) -0.0032(15) -0.0032(16) -0.0013(16) Cl3 0.0894(15) 0.0631(12) 0.0618(12) 0.0046(10) 0.0020(11) -0.0395(11) Cl4 0.0701(12) 0.0530(10) 0.0436(9) 0.0029(8) 0.0215(9) 0.0122(9) O1 0.056(3) 0.039(2) 0.057(3) -0.003(2) 0.021(2) 0.005(2) O2 0.084(4) 0.031(3) 0.091(4) -0.004(3) 0.044(3) 0.002(3) O3 0.040(2) 0.062(3) 0.037(2) -0.013(2) 0.000(2) 0.001(2) O4 0.068(3) 0.028(2) 0.053(3) -0.008(2) 0.020(2) 0.000(2) N1 0.038(3) 0.027(3) 0.047(3) -0.005(2) 0.004(2) 0.006(2) N2 0.044(3) 0.028(3) 0.036(3) -0.005(2) 0.003(2) 0.000(2) C1 0.030(3) 0.032(3) 0.034(3) 0.001(3) 0.001(2) 0.002(2) C2 0.036(3) 0.032(3) 0.040(3) 0.001(3) 0.003(3) 0.004(3) C3 0.033(3) 0.033(3) 0.044(4) 0.001(3) 0.004(3) 0.002(3) C4 0.045(4) 0.038(4) 0.055(4) 0.000(3) 0.014(3) 0.000(3) C5 0.056(4) 0.048(4) 0.054(4) 0.010(3) 0.018(4) -0.005(3) C6 0.046(4) 0.041(4) 0.062(4) 0.013(3) 0.008(3) -0.002(3) C7 0.049(4) 0.036(3) 0.056(4) 0.002(3) 0.011(3) 0.000(3) C8 0.041(4) 0.036(3) 0.043(4) 0.008(3) -0.001(3) -0.001(3) C9 0.046(4) 0.031(3) 0.050(4) 0.000(3) 0.011(3) 0.003(3) C10 0.034(3) 0.029(3) 0.041(3) -0.004(3) 0.001(3) 0.003(3) C11 0.038(3) 0.032(3) 0.035(3) -0.001(3) 0.003(3) 0.007(3) C12 0.031(3) 0.031(3) 0.031(3) 0.001(2) -0.001(2) 0.006(3) C13 0.031(3) 0.026(3) 0.030(3) 0.003(2) -0.006(2) 0.001(2) C14 0.028(3) 0.034(3) 0.032(3) 0.000(3) 0.000(2) 0.006(3) C15 0.038(3) 0.032(3) 0.036(3) -0.003(3) 0.006(3) -0.007(3) Cl1A 0.0682(13) 0.0415(12) 0.116(2) -0.0315(13) 0.0193(14) 0.0017(10) Cl2A 0.0682(13) 0.0415(12) 0.116(2) -0.0315(13) 0.0193(14) 0.0017(10) C16A 0.039(2) 0.0312(18) 0.077(4) -0.013(2) 0.015(2) -0.0053(15) C17A 0.039(2) 0.0312(18) 0.077(4) -0.013(2) 0.015(2) -0.0053(15) C18A 0.039(2) 0.0312(18) 0.077(4) -0.013(2) 0.015(2) -0.0053(15) C19A 0.039(2) 0.0312(18) 0.077(4) -0.013(2) 0.015(2) -0.0053(15) C20A 0.039(2) 0.0312(18) 0.077(4) -0.013(2) 0.015(2) -0.0053(15) C21A 0.039(2) 0.0312(18) 0.077(4) -0.013(2) 0.015(2) -0.0053(15) Cl1B 0.0682(13) 0.0415(12) 0.116(2) -0.0315(13) 0.0193(14) 0.0017(10) Cl2B 0.0682(13) 0.0415(12) 0.116(2) -0.0315(13) 0.0193(14) 0.0017(10) C16B 0.039(2) 0.0312(18) 0.077(4) -0.013(2) 0.015(2) -0.0053(15) C17B 0.039(2) 0.0312(18) 0.077(4) -0.013(2) 0.015(2) -0.0053(15) C18B 0.039(2) 0.0312(18) 0.077(4) -0.013(2) 0.015(2) -0.0053(15) C19B 0.039(2) 0.0312(18) 0.077(4) -0.013(2) 0.015(2) -0.0053(15) C20B 0.039(2) 0.0312(18) 0.077(4) -0.013(2) 0.015(2) -0.0053(15) C21B 0.039(2) 0.0312(18) 0.077(4) -0.013(2) 0.015(2) -0.0053(15) C22 0.041(3) 0.032(3) 0.034(3) 0.000(3) 0.000(3) 0.002(3) C23 0.039(3) 0.035(3) 0.036(3) 0.008(3) 0.002(3) 0.000(3) C24 0.048(4) 0.040(4) 0.041(4) -0.003(3) -0.001(3) -0.007(3) C25 0.051(4) 0.053(4) 0.041(4) 0.011(3) 0.001(3) -0.012(3) C26 0.047(4) 0.054(4) 0.049(4) 0.013(3) 0.007(3) -0.004(3) C27 0.050(4) 0.043(4) 0.040(4) 0.003(3) 0.007(3) 0.007(3) C28 0.038(3) 0.032(3) 0.043(3) 0.004(3) 0.005(3) 0.002(3) Cl5 0.0749(13) 0.0432(10) 0.0681(12) -0.0141(9) 0.0176(10) 0.0054(9) Cl6 0.0634(12) 0.0570(11) 0.0500(10) 0.0013(8) -0.0069(9) -0.0192(9) Cl7 0.0796(14) 0.0670(13) 0.0659(12) -0.0037(10) 0.0126(11) -0.0006(11) Cl8 0.1040(17) 0.0463(10) 0.0683(13) 0.0007(9) 0.0052(12) -0.0046(11) O5 0.098(4) 0.030(2) 0.051(3) -0.002(2) -0.004(3) -0.003(2) O6 0.101(4) 0.046(3) 0.062(3) -0.022(3) -0.001(3) -0.007(3) O7 0.095(4) 0.032(2) 0.057(3) -0.005(2) -0.026(3) 0.015(3) O8 0.070(3) 0.030(2) 0.051(3) -0.008(2) -0.016(2) -0.003(2) N3 0.058(3) 0.024(3) 0.036(3) -0.002(2) -0.002(3) -0.002(2) N4 0.049(3) 0.039(3) 0.050(3) -0.008(3) -0.015(3) -0.001(3) C29 0.062(4) 0.029(3) 0.038(4) 0.001(3) -0.012(3) 0.007(3) C30 0.069(5) 0.035(4) 0.051(4) 0.000(3) -0.017(4) 0.005(3) C31 0.080(5) 0.042(4) 0.039(4) -0.004(3) -0.014(4) 0.000(4) C32 0.119(7) 0.040(4) 0.050(5) 0.000(4) -0.009(5) 0.003(5) C33 0.119(8) 0.058(5) 0.054(5) 0.000(4) 0.007(5) -0.017(5) C34 0.121(8) 0.060(5) 0.040(4) 0.004(4) -0.009(5) -0.004(5) C35 0.098(6) 0.051(4) 0.035(4) -0.007(3) -0.013(4) 0.004(4) C36 0.074(5) 0.039(4) 0.046(4) 0.001(3) -0.012(4) 0.003(4) C37 0.070(5) 0.044(4) 0.053(4) -0.006(3) -0.014(4) 0.006(4) C38 0.066(5) 0.030(3) 0.044(4) -0.002(3) -0.017(3) 0.000(3) C39 0.054(4) 0.034(3) 0.049(4) -0.009(3) -0.015(3) 0.008(3) C40 0.047(4) 0.033(3) 0.047(4) -0.002(3) -0.019(3) 0.004(3) C41 0.054(4) 0.038(4) 0.042(4) -0.005(3) -0.019(3) 0.009(3) C42 0.064(4) 0.028(3) 0.042(4) 0.003(3) -0.020(3) 0.005(3) C43 0.068(5) 0.031(3) 0.042(4) -0.001(3) -0.004(3) 0.000(3) C44 0.062(4) 0.019(3) 0.035(3) 0.002(2) 0.002(3) 0.000(3) C45 0.050(4) 0.035(3) 0.037(3) 0.000(3) -0.001(3) 0.000(3) C46 0.051(4) 0.044(4) 0.037(3) 0.002(3) -0.002(3) -0.006(3) C47 0.076(5) 0.032(3) 0.036(3) -0.006(3) 0.006(3) -0.013(3) C48 0.060(4) 0.032(3) 0.035(3) 0.001(3) 0.009(3) -0.005(3) C49 0.052(4) 0.035(3) 0.035(3) -0.001(3) 0.003(3) -0.009(3) C50 0.051(4) 0.036(4) 0.049(4) -0.005(3) -0.020(3) 0.004(3) C51 0.061(5) 0.044(4) 0.039(4) -0.004(3) -0.018(3) -0.004(4) C52 0.057(4) 0.049(4) 0.047(4) -0.003(3) -0.014(3) -0.001(4) C53 0.080(6) 0.046(4) 0.047(4) -0.003(3) -0.003(4) -0.003(4) C54 0.079(6) 0.062(5) 0.039(4) 0.000(4) -0.001(4) -0.008(4) C55 0.072(5) 0.051(4) 0.043(4) -0.006(3) -0.002(4) 0.002(4) C56 0.055(4) 0.051(4) 0.039(4) -0.002(3) -0.007(3) 0.000(4) N5 0.044(3) 0.030(3) 0.042(3) 0.007(2) -0.002(2) -0.004(2) C57 0.041(4) 0.036(3) 0.038(3) 0.006(3) -0.002(3) 0.000(3) C58 0.048(4) 0.042(4) 0.044(4) 0.002(3) 0.004(3) 0.000(3) C59 0.043(4) 0.043(4) 0.044(4) -0.002(3) 0.001(3) -0.004(3) C60 0.048(4) 0.042(4) 0.063(5) -0.006(3) 0.004(3) -0.006(3) C61 0.044(4) 0.050(4) 0.040(3) 0.015(3) -0.005(3) -0.003(3) C62 0.058(4) 0.045(4) 0.046(4) -0.002(3) -0.005(3) -0.006(3) C63 0.055(5) 0.074(5) 0.047(4) -0.011(4) -0.001(3) -0.011(4) C64 0.061(5) 0.087(6) 0.071(5) -0.018(5) 0.001(4) -0.019(5) C65A 0.073(4) 0.041(2) 0.068(4) 0.001(2) -0.005(3) 0.002(3) C66A 0.073(4) 0.041(2) 0.068(4) 0.001(2) -0.005(3) 0.002(3) C67A 0.073(4) 0.041(2) 0.068(4) 0.001(2) -0.005(3) 0.002(3) C68A 0.073(4) 0.041(2) 0.068(4) 0.001(2) -0.005(3) 0.002(3) C65B 0.073(4) 0.041(2) 0.068(4) 0.001(2) -0.005(3) 0.002(3) C66B 0.073(4) 0.041(2) 0.068(4) 0.001(2) -0.005(3) 0.002(3) C67B 0.073(4) 0.041(2) 0.068(4) 0.001(2) -0.005(3) 0.002(3) C68B 0.073(4) 0.041(2) 0.068(4) 0.001(2) -0.005(3) 0.002(3) C69 0.041(4) 0.039(3) 0.046(4) 0.009(3) 0.003(3) 0.001(3) C70 0.046(4) 0.040(4) 0.062(4) 0.005(3) -0.005(3) 0.002(3) C71 0.051(5) 0.081(6) 0.059(5) 0.006(4) 0.001(4) 0.011(4) C72 0.056(5) 0.122(8) 0.064(5) -0.013(5) 0.002(4) 0.000(5) N6 0.031(3) 0.037(3) 0.040(3) 0.004(2) -0.003(2) -0.003(2) C73 0.034(3) 0.039(3) 0.047(4) -0.001(3) -0.003(3) -0.007(3) C74 0.045(4) 0.046(4) 0.046(4) 0.000(3) 0.003(3) -0.005(3) C75 0.058(5) 0.107(7) 0.060(5) 0.016(5) 0.004(4) -0.030(5) C76 0.058(5) 0.087(6) 0.070(5) 0.009(5) 0.012(4) -0.015(4) C77 0.043(4) 0.041(4) 0.040(3) 0.001(3) -0.007(3) -0.001(3) C78 0.045(4) 0.046(4) 0.040(3) 0.000(3) -0.004(3) 0.001(3) C79 0.053(4) 0.055(4) 0.045(4) 0.007(3) -0.005(3) -0.010(3) C80 0.063(5) 0.069(5) 0.048(4) 0.009(4) 0.004(4) -0.007(4) C81 0.029(3) 0.036(3) 0.048(4) 0.003(3) -0.003(3) 0.002(3) C82 0.051(4) 0.039(4) 0.043(4) -0.002(3) 0.000(3) 0.000(3) C83 0.056(4) 0.040(4) 0.043(4) 0.001(3) 0.012(3) 0.003(3) C84 0.075(5) 0.043(4) 0.057(5) -0.001(3) 0.002(4) 0.007(4) C85 0.036(3) 0.032(3) 0.037(3) 0.002(3) -0.005(3) -0.004(3) C86 0.042(4) 0.041(4) 0.051(4) 0.008(3) -0.003(3) 0.004(3) C87 0.047(4) 0.036(3) 0.055(4) 0.004(3) -0.005(3) 0.003(3) C88 0.054(4) 0.046(4) 0.066(5) -0.009(4) -0.011(4) 0.010(3) _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 Cl3 C25 1.705(3) . ? Cl4 C27 1.703(3) . ? O1 C2 1.225(7) . ? O2 C9 1.218(7) . ? O3 C15 1.235(7) . ? O4 C22 1.218(7) . ? N1 C15 1.334(7) . ? N1 C16A 1.386(6) . ? N1 C16B 1.427(6) . ? N2 C22 1.361(7) . ? N2 C23 1.408(5) . ? C1 C10 1.396(8) . ? C1 C14 1.399(8) . ? C1 C2 1.488(8) . ? C2 C3 1.470(8) . ? C3 C4 1.389(8) . ? C3 C8 1.402(8) . ? C4 C5 1.374(9) . ? C5 C6 1.381(9) . ? C6 C7 1.377(9) . ? C7 C8 1.387(8) . ? C8 C9 1.477(9) . ? C9 C10 1.487(8) . ? C10 C11 1.394(8) . ? C11 C12 1.383(8) . ? C12 C13 1.398(7) . ? C12 C22 1.500(8) . ? C13 C14 1.393(8) . ? C14 C15 1.498(8) . ? Cl1A C20A 1.677(6) . ? Cl2A C18A 1.722(6) . ? C16A C17A 1.3900 . ? C16A C21A 1.3900 . ? C17A C18A 1.3900 . ? C18A C19A 1.3900 . ? C19A C20A 1.3900 . ? C20A C21A 1.3900 . ? Cl1B C20B 1.677(6) . ? Cl2B C18B 1.723(6) . ? C16B C17B 1.3900 . ? C16B C21B 1.3900 . ? C17B C18B 1.3900 . ? C18B C19B 1.3900 . ? C19B C20B 1.3900 . ? C20B C21B 1.3900 . ? C23 C24 1.3900 . ? C23 C28 1.3900 . ? C24 C25 1.3900 . ? C25 C26 1.3900 . ? C26 C27 1.3900 . ? C27 C28 1.3900 . ? Cl5 C48 1.716(3) . ? Cl6 C46 1.710(3) . ? Cl7 C55 1.710(4) . ? Cl8 C53 1.707(4) . ? O5 C30 1.234(8) . ? O6 C37 1.219(8) . ? O7 C43 1.223(8) . ? O8 C50 1.225(7) . ? N3 C43 1.361(8) . ? N3 C44 1.409(5) . ? N4 C50 1.355(8) . ? N4 C51 1.412(6) . ? C29 C38 1.396(8) . ? C29 C42 1.404(9) . ? C29 C30 1.493(10) . ? C30 C31 1.476(10) . ? C31 C32 1.395(11) . ? C31 C36 1.402(9) . ? C32 C33 1.380(11) . ? C33 C34 1.378(11) . ? C34 C35 1.390(11) . ? C35 C36 1.394(10) . ? C36 C37 1.473(10) . ? C37 C38 1.496(10) . ? C38 C39 1.383(9) . ? C39 C40 1.378(9) . ? C40 C41 1.401(8) . ? C40 C50 1.507(9) . ? C41 C42 1.395(9) . ? C42 C43 1.511(8) . ? C44 C45 1.3900 . ? C44 C49 1.3900 . ? C45 C46 1.3900 . ? C46 C47 1.3900 . ? C47 C48 1.3900 . ? C48 C49 1.3900 . ? C51 C52 1.3900 . ? C51 C56 1.3900 . ? C52 C53 1.3900 . ? C53 C54 1.3900 . ? C54 C55 1.3900 . ? C55 C56 1.3900 . ? N5 C65B 1.442(16) . ? N5 C61 1.508(8) . ? N5 C69 1.515(8) . ? N5 C57 1.531(7) . ? N5 C65A 1.616(18) . ? C57 C58 1.509(8) . ? C58 C59 1.503(9) . ? C59 C60 1.518(9) . ? C61 C62 1.502(9) . ? C62 C63 1.521(9) . ? C63 C64 1.516(10) . ? C65A C66A 1.5397(11) . ? C66A C67A 1.5397(11) . ? C67A C68A 1.5393(11) . ? C65B C66B 1.5395(15) . ? C66B C67B 1.5397(15) . ? C67B C68B 1.5390(15) . ? C69 C70 1.507(9) . ? C70 C71 1.515(10) . ? C71 C72 1.493(11) . ? N6 C77 1.507(7) . ? N6 C85 1.513(7) . ? N6 C73 1.515(7) . ? N6 C81 1.518(7) . ? C73 C74 1.508(9) . ? C74 C75 1.501(9) . ? C75 C76 1.504(10) . ? C77 C78 1.509(9) . ? C78 C79 1.518(9) . ? C79 C80 1.504(9) . ? C81 C82 1.512(8) . ? C82 C83 1.516(9) . ? C83 C84 1.515(9) . ? C85 C86 1.513(8) . ? C86 C87 1.521(9) . ? C87 C88 1.496(9) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C15 N1 C16A 132.6(5) . . ? C15 N1 C16B 121.0(5) . . ? C16A N1 C16B 11.8(3) . . ? C22 N2 C23 125.6(4) . . ? C10 C1 C14 119.0(5) . . ? C10 C1 C2 120.2(5) . . ? C14 C1 C2 120.7(5) . . ? O1 C2 C3 122.0(5) . . ? O1 C2 C1 119.8(5) . . ? C3 C2 C1 118.1(5) . . ? C4 C3 C8 119.3(5) . . ? C4 C3 C2 119.1(5) . . ? C8 C3 C2 121.7(5) . . ? C5 C4 C3 120.2(6) . . ? C4 C5 C6 120.9(6) . . ? C7 C6 C5 119.3(6) . . ? C6 C7 C8 120.9(6) . . ? C7 C8 C3 119.3(6) . . ? C7 C8 C9 120.8(6) . . ? C3 C8 C9 119.9(5) . . ? O2 C9 C8 120.6(6) . . ? O2 C9 C10 120.6(6) . . ? C8 C9 C10 118.7(5) . . ? C11 C10 C1 120.3(5) . . ? C11 C10 C9 118.9(5) . . ? C1 C10 C9 120.8(5) . . ? C12 C11 C10 121.0(5) . . ? C11 C12 C13 118.6(5) . . ? C11 C12 C22 116.1(5) . . ? C13 C12 C22 125.3(5) . . ? C14 C13 C12 121.1(5) . . ? C13 C14 C1 119.8(5) . . ? C13 C14 C15 117.2(5) . . ? C1 C14 C15 122.5(5) . . ? O3 C15 N1 125.4(5) . . ? O3 C15 C14 117.7(5) . . ? N1 C15 C14 116.8(5) . . ? N1 C16A C17A 117.1(4) . . ? N1 C16A C21A 122.9(4) . . ? C17A C16A C21A 120.0 . . ? C18A C17A C16A 120.0 . . ? C17A C18A C19A 120.0 . . ? C17A C18A Cl2A 118.4(4) . . ? C19A C18A Cl2A 121.5(4) . . ? C20A C19A C18A 120.0 . . ? C21A C20A C19A 120.0 . . ? C21A C20A Cl1A 122.1(4) . . ? C19A C20A Cl1A 117.8(4) . . ? C20A C21A C16A 120.0 . . ? C17B C16B C21B 120.0 . . ? C17B C16B N1 115.8(4) . . ? C21B C16B N1 124.2(4) . . ? C18B C17B C16B 120.0 . . ? C19B C18B C17B 120.0 . . ? C19B C18B Cl2B 121.4(4) . . ? C17B C18B Cl2B 118.1(4) . . ? C18B C19B C20B 120.0 . . ? C21B C20B C19B 120.0 . . ? C21B C20B Cl1B 122.1(4) . . ? C19B C20B Cl1B 117.9(4) . . ? C20B C21B C16B 120.0 . . ? O4 C22 N2 123.6(5) . . ? O4 C22 C12 118.8(5) . . ? N2 C22 C12 117.6(5) . . ? C24 C23 C28 120.0 . . ? C24 C23 N2 116.4(3) . . ? C28 C23 N2 123.6(3) . . ? C25 C24 C23 120.0 . . ? C26 C25 C24 120.0 . . ? C26 C25 Cl3 119.7(2) . . ? C24 C25 Cl3 120.3(2) . . ? C27 C26 C25 120.0 . . ? C28 C27 C26 120.0 . . ? C28 C27 Cl4 119.4(2) . . ? C26 C27 Cl4 120.6(2) . . ? C27 C28 C23 120.0 . . ? C43 N3 C44 123.3(5) . . ? C50 N4 C51 125.3(5) . . ? C38 C29 C42 119.3(6) . . ? C38 C29 C30 120.1(6) . . ? C42 C29 C30 120.6(6) . . ? O5 C30 C31 120.7(7) . . ? O5 C30 C29 121.0(7) . . ? C31 C30 C29 118.2(6) . . ? C32 C31 C36 119.1(7) . . ? C32 C31 C30 119.4(6) . . ? C36 C31 C30 121.5(7) . . ? C33 C32 C31 120.5(7) . . ? C34 C33 C32 120.6(8) . . ? C33 C34 C35 120.0(8) . . ? C34 C35 C36 120.0(7) . . ? C35 C36 C31 119.9(7) . . ? C35 C36 C37 119.4(6) . . ? C31 C36 C37 120.7(7) . . ? O6 C37 C36 121.9(7) . . ? O6 C37 C38 120.1(7) . . ? C36 C37 C38 118.0(6) . . ? C39 C38 C29 120.1(6) . . ? C39 C38 C37 118.5(6) . . ? C29 C38 C37 121.4(6) . . ? C40 C39 C38 121.2(6) . . ? C39 C40 C41 119.2(6) . . ? C39 C40 C50 117.2(6) . . ? C41 C40 C50 123.6(6) . . ? C42 C41 C40 120.2(6) . . ? C41 C42 C29 119.8(6) . . ? C41 C42 C43 117.2(6) . . ? C29 C42 C43 122.8(6) . . ? O7 C43 N3 125.4(6) . . ? O7 C43 C42 120.5(6) . . ? N3 C43 C42 114.0(6) . . ? C45 C44 C49 120.0 . . ? C45 C44 N3 117.7(3) . . ? C49 C44 N3 122.2(3) . . ? C46 C45 C44 120.0 . . ? C47 C46 C45 120.0 . . ? C47 C46 Cl6 120.5(2) . . ? C45 C46 Cl6 119.5(2) . . ? C46 C47 C48 120.0 . . ? C49 C48 C47 120.0 . . ? C49 C48 Cl5 120.0(2) . . ? C47 C48 Cl5 120.0(2) . . ? C48 C49 C44 120.0 . . ? O8 C50 N4 123.9(6) . . ? O8 C50 C40 119.5(6) . . ? N4 C50 C40 116.6(6) . . ? C52 C51 C56 120.0 . . ? C52 C51 N4 124.3(4) . . ? C56 C51 N4 115.7(4) . . ? C51 C52 C53 120.0 . . ? C54 C53 C52 120.0 . . ? C54 C53 Cl8 119.8(3) . . ? C52 C53 Cl8 120.1(3) . . ? C53 C54 C55 120.0 . . ? C54 C55 C56 120.0 . . ? C54 C55 Cl7 119.9(3) . . ? C56 C55 Cl7 120.1(3) . . ? C55 C56 C51 120.0 . . ? C65B N5 C61 104.4(8) . . ? C65B N5 C69 113.1(12) . . ? C61 N5 C69 111.2(5) . . ? C65B N5 C57 110.6(13) . . ? C61 N5 C57 111.0(5) . . ? C69 N5 C57 106.6(4) . . ? C65B N5 C65A 5.2(17) . . ? C61 N5 C65A 109.0(9) . . ? C69 N5 C65A 108.7(14) . . ? C57 N5 C65A 110.3(13) . . ? C58 C57 N5 116.9(5) . . ? C59 C58 C57 110.7(5) . . ? C58 C59 C60 113.7(5) . . ? C62 C61 N5 115.7(5) . . ? C61 C62 C63 109.6(6) . . ? C64 C63 C62 112.9(6) . . ? C66A C65A N5 114.0(14) . . ? C67A C66A C65A 110.9(6) . . ? C68A C67A C66A 113.4(7) . . ? N5 C65B C66B 115.5(12) . . ? C65B C66B C67B 110.9(6) . . ? C68B C67B C66B 113.3(7) . . ? C70 C69 N5 115.8(5) . . ? C69 C70 C71 110.5(5) . . ? C72 C71 C70 112.9(7) . . ? C77 N6 C85 111.3(4) . . ? C77 N6 C73 107.0(4) . . ? C85 N6 C73 111.5(5) . . ? C77 N6 C81 110.8(5) . . ? C85 N6 C81 106.1(4) . . ? C73 N6 C81 110.3(4) . . ? C74 C73 N6 115.8(5) . . ? C75 C74 C73 110.4(6) . . ? C74 C75 C76 112.8(7) . . ? N6 C77 C78 116.6(5) . . ? C77 C78 C79 110.9(5) . . ? C80 C79 C78 112.5(6) . . ? C82 C81 N6 115.6(5) . . ? C81 C82 C83 109.8(5) . . ? C82 C83 C84 113.0(6) . . ? C86 C85 N6 114.5(5) . . ? C85 C86 C87 111.9(5) . . ? C88 C87 C86 114.3(6) . . ? 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 N1 H1 F1 0.88 1.73 2.573(6) 159.9 . N2 H2 F2 0.88 1.77 2.613(6) 159.0 . N3 H3 F2 0.88 1.73 2.575(6) 159.5 . N4 H4A F1 0.88 1.74 2.595(6) 162.0 . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.733 _refine_diff_density_min -1.299 _refine_diff_density_rms 0.165