# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Philip Gale' 'Gareth W. Bates' 'Mark E. Light' _publ_contact_author_name 'Philip Gale' _publ_contact_author_address ; Department of Chemistry University of Southampton Southampton SO17 1BJ UNITED KINGDOM ; _publ_contact_author_email PHILIP.GALE@SOTON.AC.UK _publ_requested_journal 'Chemical Communications' _publ_section_title ; Isophthalamides and pyridine-2,6-dicarboxamides with pendant indole groups: a 'twisted' binding mode for selective fluoride recognition ; data_2007sot0042 _database_code_depnum_ccdc_archive 'CCDC 640963' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C43 H61 Cl N6 O2' _chemical_formula_weight 729.43 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 16.1573(3) _cell_length_b 15.3680(3) _cell_length_c 17.4031(2) _cell_angle_alpha 90.00 _cell_angle_beta 109.8590(10) _cell_angle_gamma 90.00 _cell_volume 4064.30(12) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 53869 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.192 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1576 _exptl_absorpt_coefficient_mu 0.137 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9436 _exptl_absorpt_correction_T_max 0.9731 _exptl_absorpt_process_details ; SADABS V2.10 (Sheldrick, G.M., 2003) ; _exptl_special_details ; SADABS was used to perform the Absorption correction Parameter refinement on 32158 reflections reduced R(int) from 0.0872 to 0.0515 Ratio of minimum to maximum apparent transmission: 0.720030 The given Tmin and Tmax were generated using the SHELX SIZE command ; _diffrn_ambient_temperature 120(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 CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \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 51747 _diffrn_reflns_av_R_equivalents 0.0674 _diffrn_reflns_av_sigmaI/netI 0.0564 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 27.48 _reflns_number_total 9289 _reflns_number_gt 6598 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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. ; _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^)+(0.0576P)^2^+1.1055P] 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 0.0063(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 9289 _refine_ls_number_parameters 494 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0811 _refine_ls_R_factor_gt 0.0491 _refine_ls_wR_factor_ref 0.1258 _refine_ls_wR_factor_gt 0.1124 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.006 _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 Cl1 Cl 0.97707(3) 0.36630(3) 0.22315(2) 0.02524(12) Uani 1 1 d . . . N1 N 0.93801(9) 0.40720(10) 0.03723(9) 0.0232(3) Uani 1 1 d . . . N2 N 0.81655(10) 0.50201(10) 0.10617(8) 0.0238(3) Uani 1 1 d . . . N3 N 0.87004(9) 0.52706(9) 0.27001(8) 0.0213(3) Uani 1 1 d . . . N4 N 1.04934(9) 0.52351(10) 0.36037(9) 0.0233(3) Uani 1 1 d . . . N5 N 1.17424(10) 0.39512(10) 0.32683(9) 0.0262(3) Uani 1 1 d . . . N6 N 1.47967(9) 0.68592(9) 0.06944(8) 0.0214(3) Uani 1 1 d . . . H98 H 0.9548(13) 0.3946(13) 0.0914(13) 0.035(5) Uiso 1 1 d . . . H99 H 0.8700(14) 0.4930(13) 0.1405(12) 0.036(6) Uiso 1 1 d . . . H97 H 1.0258(13) 0.4904(14) 0.3153(13) 0.040(6) Uiso 1 1 d . . . H96 H 1.1214(14) 0.3818(13) 0.2924(12) 0.037(6) Uiso 1 1 d . . . O1 O 0.67247(8) 0.50322(8) 0.09971(7) 0.0262(3) Uani 1 1 d . . . O2 O 1.01445(8) 0.59365(8) 0.46161(7) 0.0277(3) Uani 1 1 d . . . C1 C 1.05865(12) 0.32160(12) 0.01537(11) 0.0300(4) Uani 1 1 d . . . H1A H 1.0753 0.3004 -0.0304 0.045 Uiso 1 1 calc R . . H1B H 1.0472 0.2720 0.0457 0.045 Uiso 1 1 calc R . . H1C H 1.1066 0.3567 0.0518 0.045 Uiso 1 1 calc R . . C2 C 0.97765(11) 0.37594(11) -0.01648(10) 0.0240(4) Uani 1 1 d . . . C3 C 0.93130(11) 0.40361(11) -0.09402(10) 0.0248(4) Uani 1 1 d . . . C4 C 0.95361(13) 0.38985(13) -0.16995(11) 0.0328(4) Uani 1 1 d . . . H4A H 0.9711 0.4454 -0.1875 0.049 Uiso 1 1 calc R . . H4B H 0.9020 0.3669 -0.2133 0.049 Uiso 1 1 calc R . . H4C H 1.0023 0.3483 -0.1587 0.049 Uiso 1 1 calc R . . C5 C 0.85880(11) 0.45448(11) -0.08892(10) 0.0234(4) Uani 1 1 d . . . C6 C 0.78973(12) 0.49904(12) -0.14635(11) 0.0285(4) Uani 1 1 d . . . H6 H 0.7839 0.4988 -0.2025 0.034 Uiso 1 1 calc R . . C7 C 0.73017(12) 0.54333(12) -0.11966(10) 0.0289(4) Uani 1 1 d . . . H7 H 0.6829 0.5735 -0.1584 0.035 Uiso 1 1 calc R . . C8 C 0.73764(11) 0.54500(12) -0.03695(10) 0.0268(4) Uani 1 1 d . . . H8 H 0.6961 0.5769 -0.0206 0.032 Uiso 1 1 calc R . . C9 C 0.80502(11) 0.50058(11) 0.02128(10) 0.0230(4) Uani 1 1 d . . . C10 C 0.86544(11) 0.45566(11) -0.00569(10) 0.0220(4) Uani 1 1 d . . . C11 C 0.75212(11) 0.50491(11) 0.13908(10) 0.0215(4) Uani 1 1 d . . . C12 C 0.78403(11) 0.51207(11) 0.23098(10) 0.0218(4) Uani 1 1 d . . . C13 C 0.72312(11) 0.50511(11) 0.27125(10) 0.0248(4) Uani 1 1 d . . . H13 H 0.6628 0.4943 0.2415 0.030 Uiso 1 1 calc R . . C14 C 0.75201(12) 0.51416(12) 0.35542(11) 0.0278(4) Uani 1 1 d . . . H14 H 0.7120 0.5095 0.3845 0.033 Uiso 1 1 calc R . . C15 C 0.84010(12) 0.53011(11) 0.39622(10) 0.0257(4) Uani 1 1 d . . . H15 H 0.8616 0.5373 0.4539 0.031 Uiso 1 1 calc R . . C16 C 0.89698(11) 0.53549(11) 0.35158(10) 0.0214(4) Uani 1 1 d . . . C17 C 0.99275(11) 0.55376(11) 0.39643(10) 0.0221(4) Uani 1 1 d . . . C18 C 1.14259(11) 0.53220(12) 0.39179(9) 0.0234(4) Uani 1 1 d . . . C19 C 1.18486(12) 0.60201(12) 0.44047(10) 0.0287(4) Uani 1 1 d . . . H19 H 1.1507 0.6473 0.4519 0.034 Uiso 1 1 calc R . . C20 C 1.27682(13) 0.60645(13) 0.47279(11) 0.0325(4) Uani 1 1 d . . . H20 H 1.3037 0.6550 0.5055 0.039 Uiso 1 1 calc R . . C21 C 1.32926(12) 0.54231(13) 0.45847(10) 0.0317(4) Uani 1 1 d . . . H21 H 1.3915 0.5453 0.4827 0.038 Uiso 1 1 calc R . . C22 C 1.28916(11) 0.47245(12) 0.40740(10) 0.0260(4) Uani 1 1 d . . . C23 C 1.19632(11) 0.46888(12) 0.37434(10) 0.0241(4) Uani 1 1 d . . . C24 C 1.41693(12) 0.37093(15) 0.40082(12) 0.0369(5) Uani 1 1 d . . . H24A H 1.4205 0.3117 0.3814 0.055 Uiso 1 1 calc R . . H24B H 1.4448 0.3729 0.4604 0.055 Uiso 1 1 calc R . . H24C H 1.4474 0.4111 0.3757 0.055 Uiso 1 1 calc R . . C25 C 1.32205(12) 0.39728(13) 0.37787(10) 0.0287(4) Uani 1 1 d . . . C26 C 1.25079(12) 0.35318(12) 0.32820(10) 0.0272(4) Uani 1 1 d . . . C27 C 1.24550(13) 0.27191(13) 0.27920(12) 0.0362(5) Uani 1 1 d . . . H27A H 1.2935 0.2714 0.2568 0.054 Uiso 1 1 calc R . . H27B H 1.1889 0.2702 0.2344 0.054 Uiso 1 1 calc R . . H27C H 1.2506 0.2210 0.3144 0.054 Uiso 1 1 calc R . . C28 C 1.39602(11) 0.74043(11) 0.04578(10) 0.0244(4) Uani 1 1 d . . . H28A H 1.3984 0.7775 0.0930 0.029 Uiso 1 1 calc R . . H28B H 1.3959 0.7796 0.0006 0.029 Uiso 1 1 calc R . . C29 C 1.30941(12) 0.69069(12) 0.01937(11) 0.0297(4) Uani 1 1 d . . . H29A H 1.2970 0.6700 0.0682 0.036 Uiso 1 1 calc R . . H29B H 1.3138 0.6393 -0.0133 0.036 Uiso 1 1 calc R . . C30 C 1.23440(12) 0.74986(13) -0.03164(12) 0.0368(5) Uani 1 1 d . . . H30A H 1.1777 0.7265 -0.0306 0.044 Uiso 1 1 calc R . . H30B H 1.2424 0.8086 -0.0069 0.044 Uiso 1 1 calc R . . C31 C 1.23096(15) 0.75694(15) -0.11937(13) 0.0489(6) Uani 1 1 d . . . H31A H 1.2879 0.7773 -0.1207 0.073 Uiso 1 1 calc R . . H31B H 1.1849 0.7983 -0.1487 0.073 Uiso 1 1 calc R . . H31C H 1.2178 0.6997 -0.1456 0.073 Uiso 1 1 calc R . . C32 C 1.48822(11) 0.63851(11) -0.00442(9) 0.0213(4) Uani 1 1 d . . . H32A H 1.5363 0.5953 0.0151 0.026 Uiso 1 1 calc R . . H32B H 1.4330 0.6061 -0.0315 0.026 Uiso 1 1 calc R . . C33 C 1.50662(12) 0.69648(12) -0.06740(10) 0.0271(4) Uani 1 1 d . . . H33A H 1.5655 0.7233 -0.0432 0.032 Uiso 1 1 calc R . . H33B H 1.4625 0.7438 -0.0832 0.032 Uiso 1 1 calc R . . C34 C 1.50328(12) 0.64480(12) -0.14292(10) 0.0269(4) Uani 1 1 d . . . H34A H 1.4422 0.6250 -0.1716 0.032 Uiso 1 1 calc R . . H34B H 1.5412 0.5927 -0.1263 0.032 Uiso 1 1 calc R . . C35 C 1.53436(13) 0.69992(14) -0.20081(11) 0.0353(5) Uani 1 1 d . . . H35A H 1.4976 0.7521 -0.2164 0.053 Uiso 1 1 calc R . . H35B H 1.5296 0.6660 -0.2498 0.053 Uiso 1 1 calc R . . H35C H 1.5958 0.7170 -0.1734 0.053 Uiso 1 1 calc R . . C36 C 1.55459(11) 0.75014(11) 0.10499(10) 0.0230(4) Uani 1 1 d . . . H36A H 1.5506 0.7954 0.0634 0.028 Uiso 1 1 calc R . . H36B H 1.5459 0.7793 0.1524 0.028 Uiso 1 1 calc R . . C37 C 1.64653(11) 0.71203(11) 0.13233(11) 0.0270(4) Uani 1 1 d . . . H37A H 1.6545 0.6768 0.0877 0.032 Uiso 1 1 calc R . . H37B H 1.6554 0.6737 0.1802 0.032 Uiso 1 1 calc R . . C38 C 1.71337(12) 0.78600(12) 0.15487(11) 0.0332(4) Uani 1 1 d . . . H38A H 1.7015 0.8257 0.1075 0.040 Uiso 1 1 calc R . . H38B H 1.7057 0.8196 0.2005 0.040 Uiso 1 1 calc R . . C39 C 1.80752(14) 0.75457(16) 0.17967(15) 0.0514(6) Uani 1 1 d . . . H39A H 1.8214 0.7196 0.2296 0.077 Uiso 1 1 calc R . . H39B H 1.8472 0.8048 0.1898 0.077 Uiso 1 1 calc R . . H39C H 1.8149 0.7190 0.1357 0.077 Uiso 1 1 calc R . . C40 C 1.47930(12) 0.61533(11) 0.13044(10) 0.0241(4) Uani 1 1 d . . . H40A H 1.4286 0.5764 0.1049 0.029 Uiso 1 1 calc R . . H40B H 1.5335 0.5802 0.1419 0.029 Uiso 1 1 calc R . . C41 C 1.47404(14) 0.64782(12) 0.21108(11) 0.0349(5) Uani 1 1 d . . . H41A H 1.5209 0.6915 0.2345 0.042 Uiso 1 1 calc R . . H41B H 1.4166 0.6769 0.2010 0.042 Uiso 1 1 calc R . . C42 C 1.48404(13) 0.57524(13) 0.27194(11) 0.0332(4) Uani 1 1 d . . . H42A H 1.5392 0.5432 0.2787 0.040 Uiso 1 1 calc R . . H42B H 1.4345 0.5340 0.2504 0.040 Uiso 1 1 calc R . . C43 C 1.48596(17) 0.60849(15) 0.35424(12) 0.0480(6) Uani 1 1 d . . . H43A H 1.5324 0.6523 0.3741 0.072 Uiso 1 1 calc R . . H43B H 1.4978 0.5600 0.3931 0.072 Uiso 1 1 calc R . . H43C H 1.4290 0.6347 0.3489 0.072 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 Cl1 0.0301(2) 0.0220(2) 0.0221(2) 0.00136(16) 0.00685(17) 0.00191(18) N1 0.0223(8) 0.0272(8) 0.0201(7) 0.0016(6) 0.0070(6) -0.0011(6) N2 0.0202(8) 0.0306(9) 0.0201(7) -0.0002(6) 0.0060(6) 0.0011(6) N3 0.0237(8) 0.0172(7) 0.0237(7) 0.0005(6) 0.0087(6) 0.0025(6) N4 0.0227(8) 0.0267(8) 0.0196(7) -0.0019(6) 0.0059(6) 0.0010(6) N5 0.0245(8) 0.0275(9) 0.0272(8) -0.0009(6) 0.0096(7) 0.0001(7) N6 0.0281(8) 0.0174(7) 0.0197(7) -0.0010(6) 0.0097(6) -0.0015(6) O1 0.0210(7) 0.0270(7) 0.0295(6) -0.0042(5) 0.0071(5) -0.0011(5) O2 0.0348(7) 0.0247(7) 0.0244(6) -0.0052(5) 0.0109(5) -0.0002(6) C1 0.0287(10) 0.0284(10) 0.0341(10) 0.0006(8) 0.0121(8) 0.0000(8) C2 0.0248(9) 0.0209(9) 0.0284(9) -0.0025(7) 0.0120(7) -0.0051(7) C3 0.0289(10) 0.0226(9) 0.0248(9) -0.0024(7) 0.0116(7) -0.0045(7) C4 0.0381(11) 0.0357(11) 0.0282(9) -0.0021(8) 0.0161(8) -0.0020(9) C5 0.0253(9) 0.0229(9) 0.0222(8) 0.0002(7) 0.0084(7) -0.0052(7) C6 0.0315(10) 0.0321(11) 0.0204(8) 0.0025(7) 0.0070(7) -0.0038(8) C7 0.0254(10) 0.0325(11) 0.0251(9) 0.0046(8) 0.0035(7) 0.0011(8) C8 0.0241(9) 0.0281(10) 0.0276(9) -0.0008(7) 0.0079(7) -0.0010(8) C9 0.0222(9) 0.0246(9) 0.0225(8) -0.0014(7) 0.0080(7) -0.0050(7) C10 0.0206(9) 0.0216(9) 0.0221(8) 0.0005(7) 0.0050(7) -0.0039(7) C11 0.0221(9) 0.0156(8) 0.0270(9) -0.0009(7) 0.0084(7) 0.0003(7) C12 0.0259(9) 0.0147(8) 0.0257(9) 0.0015(7) 0.0099(7) 0.0041(7) C13 0.0222(9) 0.0237(9) 0.0296(9) 0.0015(7) 0.0101(7) 0.0027(7) C14 0.0319(10) 0.0272(10) 0.0299(9) 0.0049(8) 0.0179(8) 0.0050(8) C15 0.0321(10) 0.0245(10) 0.0227(8) 0.0039(7) 0.0122(7) 0.0057(8) C16 0.0284(9) 0.0161(8) 0.0213(8) 0.0011(6) 0.0105(7) 0.0045(7) C17 0.0295(10) 0.0173(9) 0.0207(8) 0.0024(7) 0.0103(7) 0.0012(7) C18 0.0243(9) 0.0288(10) 0.0173(8) 0.0030(7) 0.0075(7) -0.0004(7) C19 0.0312(10) 0.0294(10) 0.0272(9) -0.0017(8) 0.0123(8) -0.0013(8) C20 0.0362(11) 0.0343(11) 0.0277(9) -0.0058(8) 0.0118(8) -0.0088(9) C21 0.0240(10) 0.0456(12) 0.0255(9) -0.0008(8) 0.0085(7) -0.0053(9) C22 0.0257(10) 0.0339(10) 0.0197(8) 0.0039(7) 0.0095(7) 0.0001(8) C23 0.0264(9) 0.0280(10) 0.0186(8) 0.0024(7) 0.0085(7) -0.0009(8) C24 0.0300(11) 0.0480(13) 0.0340(10) -0.0007(9) 0.0128(8) 0.0062(9) C25 0.0279(10) 0.0356(11) 0.0251(9) 0.0044(8) 0.0124(7) 0.0031(8) C26 0.0289(10) 0.0283(10) 0.0278(9) 0.0034(8) 0.0141(8) 0.0046(8) C27 0.0332(11) 0.0350(12) 0.0440(11) -0.0037(9) 0.0176(9) 0.0014(9) C28 0.0288(10) 0.0195(9) 0.0265(9) 0.0002(7) 0.0117(7) 0.0019(7) C29 0.0313(10) 0.0266(10) 0.0343(10) 0.0009(8) 0.0151(8) -0.0015(8) C30 0.0281(11) 0.0306(11) 0.0499(12) 0.0029(9) 0.0107(9) -0.0010(8) C31 0.0499(14) 0.0386(13) 0.0439(12) 0.0019(10) -0.0025(10) -0.0099(11) C32 0.0281(9) 0.0165(8) 0.0203(8) -0.0033(6) 0.0096(7) -0.0031(7) C33 0.0365(10) 0.0223(9) 0.0248(9) -0.0011(7) 0.0137(8) -0.0030(8) C34 0.0296(10) 0.0304(10) 0.0211(8) -0.0021(7) 0.0092(7) -0.0028(8) C35 0.0402(12) 0.0425(12) 0.0266(9) 0.0024(9) 0.0156(8) 0.0008(9) C36 0.0317(10) 0.0159(8) 0.0214(8) -0.0023(7) 0.0092(7) -0.0038(7) C37 0.0309(10) 0.0207(9) 0.0265(9) -0.0011(7) 0.0060(7) -0.0052(8) C38 0.0334(11) 0.0288(11) 0.0316(10) -0.0006(8) 0.0035(8) -0.0098(8) C39 0.0322(12) 0.0469(14) 0.0633(15) 0.0077(11) 0.0010(10) -0.0106(10) C40 0.0326(10) 0.0185(9) 0.0235(8) 0.0018(7) 0.0125(7) -0.0025(7) C41 0.0578(14) 0.0252(10) 0.0277(10) -0.0005(8) 0.0224(9) 0.0003(9) C42 0.0423(12) 0.0309(11) 0.0287(9) 0.0015(8) 0.0149(8) -0.0009(9) C43 0.0745(17) 0.0471(14) 0.0295(10) 0.0019(10) 0.0267(11) -0.0050(12) _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 C10 1.376(2) . ? N1 C2 1.386(2) . ? N2 C11 1.349(2) . ? N2 C9 1.425(2) . ? N3 C16 1.342(2) . ? N3 C12 1.343(2) . ? N4 C17 1.355(2) . ? N4 C18 1.424(2) . ? N5 C23 1.377(2) . ? N5 C26 1.388(2) . ? N6 C40 1.519(2) . ? N6 C36 1.521(2) . ? N6 C28 1.523(2) . ? N6 C32 1.524(2) . ? O1 C11 1.236(2) . ? O2 C17 1.2310(19) . ? C1 C2 1.492(2) . ? C2 C3 1.370(2) . ? C3 C5 1.436(2) . ? C3 C4 1.498(2) . ? C5 C6 1.398(2) . ? C5 C10 1.416(2) . ? C6 C7 1.382(3) . ? C7 C8 1.403(2) . ? C8 C9 1.389(2) . ? C9 C10 1.401(2) . ? C11 C12 1.509(2) . ? C12 C13 1.393(2) . ? C13 C14 1.385(2) . ? C14 C15 1.380(3) . ? C15 C16 1.393(2) . ? C16 C17 1.504(2) . ? C18 C19 1.393(2) . ? C18 C23 1.404(2) . ? C19 C20 1.400(3) . ? C20 C21 1.377(3) . ? C21 C22 1.404(3) . ? C22 C23 1.413(2) . ? C22 C25 1.438(3) . ? C24 C25 1.503(3) . ? C25 C26 1.362(3) . ? C26 C27 1.498(3) . ? C28 C29 1.522(2) . ? C29 C30 1.534(3) . ? C30 C31 1.513(3) . ? C32 C33 1.518(2) . ? C33 C34 1.521(2) . ? C34 C35 1.526(2) . ? C36 C37 1.515(2) . ? C37 C38 1.525(2) . ? C38 C39 1.513(3) . ? C40 C41 1.519(2) . ? C41 C42 1.509(3) . ? C42 C43 1.511(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 C10 N1 C2 108.99(14) . . ? C11 N2 C9 126.35(15) . . ? C16 N3 C12 117.34(14) . . ? C17 N4 C18 125.62(14) . . ? C23 N5 C26 108.93(15) . . ? C40 N6 C36 111.76(12) . . ? C40 N6 C28 111.58(12) . . ? C36 N6 C28 105.28(12) . . ? C40 N6 C32 105.73(12) . . ? C36 N6 C32 111.45(12) . . ? C28 N6 C32 111.18(12) . . ? C3 C2 N1 109.48(15) . . ? C3 C2 C1 131.06(15) . . ? N1 C2 C1 119.45(15) . . ? C2 C3 C5 107.01(14) . . ? C2 C3 C4 127.62(16) . . ? C5 C3 C4 125.25(16) . . ? C6 C5 C10 119.33(16) . . ? C6 C5 C3 133.80(16) . . ? C10 C5 C3 106.87(14) . . ? C7 C6 C5 118.61(16) . . ? C6 C7 C8 121.80(17) . . ? C9 C8 C7 120.83(17) . . ? C8 C9 C10 117.43(15) . . ? C8 C9 N2 122.89(16) . . ? C10 C9 N2 119.64(15) . . ? N1 C10 C9 130.36(15) . . ? N1 C10 C5 107.64(14) . . ? C9 C10 C5 122.00(15) . . ? O1 C11 N2 124.93(15) . . ? O1 C11 C12 120.39(15) . . ? N2 C11 C12 114.68(15) . . ? N3 C12 C13 123.05(15) . . ? N3 C12 C11 118.09(14) . . ? C13 C12 C11 118.84(15) . . ? C14 C13 C12 118.85(16) . . ? C15 C14 C13 118.71(16) . . ? C14 C15 C16 118.96(16) . . ? N3 C16 C15 123.09(16) . . ? N3 C16 C17 118.27(14) . . ? C15 C16 C17 118.63(14) . . ? O2 C17 N4 124.88(16) . . ? O2 C17 C16 119.47(15) . . ? N4 C17 C16 115.65(14) . . ? C19 C18 C23 116.97(16) . . ? C19 C18 N4 122.82(16) . . ? C23 C18 N4 120.21(15) . . ? C18 C19 C20 121.05(17) . . ? C21 C20 C19 121.78(18) . . ? C20 C21 C22 118.82(17) . . ? C21 C22 C23 119.02(17) . . ? C21 C22 C25 133.93(17) . . ? C23 C22 C25 107.05(16) . . ? N5 C23 C18 130.34(16) . . ? N5 C23 C22 107.41(15) . . ? C18 C23 C22 122.25(16) . . ? C26 C25 C22 106.94(16) . . ? C26 C25 C24 126.92(17) . . ? C22 C25 C24 126.09(17) . . ? C25 C26 N5 109.64(16) . . ? C25 C26 C27 130.42(17) . . ? N5 C26 C27 119.94(16) . . ? C29 C28 N6 116.48(14) . . ? C28 C29 C30 109.97(15) . . ? C31 C30 C29 112.19(17) . . ? C33 C32 N6 115.12(13) . . ? C32 C33 C34 111.06(14) . . ? C33 C34 C35 110.95(15) . . ? C37 C36 N6 115.89(14) . . ? C36 C37 C38 109.01(15) . . ? C39 C38 C37 113.03(17) . . ? C41 C40 N6 115.19(14) . . ? C42 C41 C40 112.30(15) . . ? C41 C42 C43 112.23(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 H98 Cl1 0.91(2) 2.24(2) 3.1425(15) 172.2(17) . N2 H99 Cl1 0.88(2) 2.68(2) 3.4108(16) 141.9(17) . N4 H97 Cl1 0.90(2) 2.44(2) 3.3179(16) 162.9(18) . N5 H96 Cl1 0.88(2) 2.24(2) 3.1137(17) 167.5(18) . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.349 _refine_diff_density_min -0.350 _refine_diff_density_rms 0.089 #==END data_2007sot0043 _database_code_depnum_ccdc_archive 'CCDC 640964' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C43 H61 F N6 O2' _chemical_formula_weight 712.98 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.8813(4) _cell_length_b 18.1336(7) _cell_length_c 11.4775(5) _cell_angle_alpha 90.00 _cell_angle_beta 103.333(2) _cell_angle_gamma 90.00 _cell_volume 2001.15(14) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 4605 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Fragment _exptl_crystal_colour 'Pale Yellow' _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.183 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 772 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9733 _exptl_absorpt_correction_T_max 0.9977 _exptl_absorpt_process_details ; SADABS V2.10 (Sheldrick, G.M., 2003) ; _exptl_special_details ; SADABS was used to perform the Absorption correction Parameter refinement on 15690 reflections reduced R(int) from 0.1128 to 0.0546 Ratio of minimum to maximum apparent transmission: 0.881020 The given Tmin and Tmax were generated using the SHELX SIZE command ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker Nonius FR591 Rotating Anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \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 17825 _diffrn_reflns_av_R_equivalents 0.0580 _diffrn_reflns_av_sigmaI/netI 0.0651 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.30 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4709 _reflns_number_gt 3656 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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. ; _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^)+(0.0000P)^2^+2.3413P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4709 _refine_ls_number_parameters 493 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1058 _refine_ls_R_factor_gt 0.0754 _refine_ls_wR_factor_ref 0.1484 _refine_ls_wR_factor_gt 0.1329 _refine_ls_goodness_of_fit_ref 1.155 _refine_ls_restrained_S_all 1.155 _refine_ls_shift/su_max 0.019 _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 F1 F 0.8748(3) 0.44026(17) 0.6007(3) 0.0419(8) Uani 1 1 d . . . O1 O 0.4573(3) 0.4455(2) 0.2683(3) 0.0354(8) Uani 1 1 d . . . O2 O 0.6700(4) 0.6275(2) 0.8184(4) 0.0454(10) Uani 1 1 d . . . N1 N 0.8688(4) 0.3056(2) 0.5319(3) 0.0259(9) Uani 1 1 d . . . N2 N 0.6542(4) 0.4093(2) 0.4060(4) 0.0285(9) Uani 1 1 d . . . N3 N 0.6095(4) 0.5176(2) 0.5563(4) 0.0300(9) Uani 1 1 d . . . N4 N 0.8129(4) 0.5429(2) 0.7616(4) 0.0306(10) Uani 1 1 d . . . N5 N 1.0939(4) 0.4873(2) 0.7493(4) 0.0302(9) Uani 1 1 d . . . H98 H 0.709(5) 0.426(3) 0.477(4) 0.028(13) Uiso 1 1 d . . . H96 H 1.031(5) 0.471(3) 0.691(5) 0.030(14) Uiso 1 1 d . . . H99 H 0.874(5) 0.346(3) 0.572(4) 0.028(14) Uiso 1 1 d . . . H97 H 0.822(6) 0.515(4) 0.702(5) 0.054(19) Uiso 1 1 d . . . C1 C 1.0568(6) 0.2415(3) 0.6761(5) 0.0410(14) Uani 1 1 d . . . H1A H 1.1200 0.1998 0.6763 0.061 Uiso 1 1 calc R . . H1B H 1.0044 0.2339 0.7379 0.061 Uiso 1 1 calc R . . H1C H 1.1109 0.2872 0.6927 0.061 Uiso 1 1 calc R . . C2 C 0.9588(5) 0.2470(3) 0.5572(4) 0.0282(11) Uani 1 1 d . . . C3 C 0.9407(5) 0.2006(3) 0.4606(4) 0.0286(11) Uani 1 1 d . . . C4 C 1.0139(6) 0.1292(3) 0.4508(5) 0.0363(12) Uani 1 1 d . . . H4A H 1.0939 0.1243 0.5190 0.054 Uiso 1 1 calc R . . H4B H 1.0460 0.1287 0.3761 0.054 Uiso 1 1 calc R . . H4C H 0.9496 0.0881 0.4508 0.054 Uiso 1 1 calc R . . C5 C 0.8331(5) 0.2325(3) 0.3687(4) 0.0245(10) Uani 1 1 d . . . C6 C 0.7674(5) 0.2109(3) 0.2512(4) 0.0288(11) Uani 1 1 d . . . H6 H 0.7912 0.1660 0.2180 0.035 Uiso 1 1 calc R . . C7 C 0.6680(5) 0.2571(3) 0.1872(4) 0.0344(12) Uani 1 1 d . . . H7 H 0.6236 0.2437 0.1076 0.041 Uiso 1 1 calc R . . C8 C 0.6285(5) 0.3231(3) 0.2328(4) 0.0309(11) Uani 1 1 d . . . H8 H 0.5599 0.3534 0.1838 0.037 Uiso 1 1 calc R . . C9 C 0.6891(4) 0.3450(3) 0.3500(4) 0.0249(10) Uani 1 1 d . . . C10 C 0.7926(5) 0.2983(3) 0.4159(4) 0.0240(10) Uani 1 1 d . . . C11 C 0.5399(5) 0.4521(3) 0.3656(5) 0.0298(11) Uani 1 1 d . . . C12 C 0.5157(5) 0.5106(3) 0.4516(5) 0.0313(11) Uani 1 1 d . . . C13 C 0.3959(5) 0.5535(3) 0.4215(5) 0.0385(13) Uani 1 1 d . . . H13 H 0.3324 0.5475 0.3462 0.046 Uiso 1 1 calc R . . C14 C 0.3710(6) 0.6042(3) 0.5017(6) 0.0428(14) Uani 1 1 d . . . H14 H 0.2896 0.6338 0.4831 0.051 Uiso 1 1 calc R . . C15 C 0.4656(6) 0.6119(3) 0.6104(6) 0.0410(14) Uani 1 1 d . . . H15 H 0.4497 0.6461 0.6686 0.049 Uiso 1 1 calc R . . C16 C 0.5847(5) 0.5684(3) 0.6324(5) 0.0334(12) Uani 1 1 d . . . C17 C 0.6934(5) 0.5815(3) 0.7469(5) 0.0338(12) Uani 1 1 d . . . C18 C 0.9333(5) 0.5538(3) 0.8547(4) 0.0297(11) Uani 1 1 d . . . C19 C 0.9341(6) 0.5923(3) 0.9599(5) 0.0387(13) Uani 1 1 d . . . H19 H 0.8493 0.6111 0.9735 0.046 Uiso 1 1 calc R . . C20 C 1.0577(7) 0.6034(3) 1.0455(5) 0.0406(14) Uani 1 1 d . . . H20 H 1.0540 0.6295 1.1165 0.049 Uiso 1 1 calc R . . C21 C 1.1853(6) 0.5785(3) 1.0321(5) 0.0402(13) Uani 1 1 d . . . H21 H 1.2680 0.5881 1.0912 0.048 Uiso 1 1 calc R . . C22 C 1.1883(6) 0.5381(3) 0.9274(4) 0.0336(12) Uani 1 1 d . . . C23 C 1.0628(5) 0.5258(3) 0.8419(4) 0.0278(10) Uani 1 1 d . . . C24 C 1.4486(6) 0.5058(4) 0.9435(5) 0.0462(15) Uani 1 1 d . . . H24A H 1.4992 0.4722 0.9018 0.069 Uiso 1 1 calc R . . H24B H 1.4600 0.4896 1.0267 0.069 Uiso 1 1 calc R . . H24C H 1.4856 0.5558 0.9420 0.069 Uiso 1 1 calc R . . C25 C 1.2969(5) 0.5053(3) 0.8821(4) 0.0319(11) Uani 1 1 d . . . C26 C 1.2348(5) 0.4748(3) 0.7734(4) 0.0290(11) Uani 1 1 d . . . C27 C 1.2964(5) 0.4361(3) 0.6832(5) 0.0354(12) Uani 1 1 d . . . H27A H 1.2554 0.3868 0.6680 0.053 Uiso 1 1 calc R . . H27B H 1.3972 0.4317 0.7138 0.053 Uiso 1 1 calc R . . H27C H 1.2771 0.4644 0.6084 0.053 Uiso 1 1 calc R . . N6 N 1.1060(4) 0.3387(2) 1.1398(4) 0.0296(9) Uani 1 1 d . . . C28 C 1.2157(5) 0.3473(3) 1.0673(4) 0.0298(11) Uani 1 1 d . . . H28A H 1.1819 0.3836 1.0026 0.036 Uiso 1 1 calc R . . H28B H 1.3010 0.3678 1.1200 0.036 Uiso 1 1 calc R . . C29 C 1.2533(5) 0.2766(3) 1.0116(4) 0.0315(11) Uani 1 1 d . . . H29A H 1.2929 0.2410 1.0759 0.038 Uiso 1 1 calc R . . H29B H 1.1679 0.2545 0.9613 0.038 Uiso 1 1 calc R . . C30 C 1.3572(5) 0.2899(3) 0.9356(4) 0.0324(11) Uani 1 1 d . . . H30A H 1.4392 0.3160 0.9839 0.039 Uiso 1 1 calc R . . H30B H 1.3146 0.3219 0.8670 0.039 Uiso 1 1 calc R . . C31 C 1.4042(6) 0.2178(3) 0.8889(5) 0.0383(13) Uani 1 1 d . . . H31A H 1.4532 0.1877 0.9565 0.058 Uiso 1 1 calc R . . H31B H 1.4669 0.2286 0.8362 0.058 Uiso 1 1 calc R . . H31C H 1.3229 0.1908 0.8440 0.058 Uiso 1 1 calc R . . C32 C 1.1509(5) 0.2829(3) 1.2395(5) 0.0327(11) Uani 1 1 d . . . H32A H 1.1618 0.2343 1.2036 0.039 Uiso 1 1 calc R . . H32B H 1.0764 0.2783 1.2837 0.039 Uiso 1 1 calc R . . C33 C 1.2869(5) 0.3024(3) 1.3285(5) 0.0364(12) Uani 1 1 d . . . H33A H 1.3665 0.2925 1.2918 0.044 Uiso 1 1 calc R . . H33B H 1.2874 0.3555 1.3484 0.044 Uiso 1 1 calc R . . C34 C 1.3020(6) 0.2568(3) 1.4423(5) 0.0377(13) Uani 1 1 d . . . H34A H 1.2226 0.2671 1.4790 0.045 Uiso 1 1 calc R . . H34B H 1.2997 0.2037 1.4218 0.045 Uiso 1 1 calc R . . C35 C 1.4375(6) 0.2742(4) 1.5323(5) 0.0480(15) Uani 1 1 d . . . H35A H 1.5163 0.2623 1.4972 0.072 Uiso 1 1 calc R . . H35B H 1.4433 0.2447 1.6048 0.072 Uiso 1 1 calc R . . H35C H 1.4400 0.3267 1.5527 0.072 Uiso 1 1 calc R . . C36 C 0.9702(5) 0.3095(3) 1.0634(5) 0.0356(12) Uani 1 1 d . . . H36A H 0.9859 0.2580 1.0406 0.043 Uiso 1 1 calc R . . H36B H 0.9011 0.3079 1.1136 0.043 Uiso 1 1 calc R . . C37 C 0.9073(6) 0.3516(3) 0.9509(5) 0.0442(14) Uani 1 1 d . . . H37A H 0.9692 0.3486 0.8944 0.053 Uiso 1 1 calc R . . H37B H 0.8966 0.4041 0.9703 0.053 Uiso 1 1 calc R . . C38 C 0.7652(6) 0.3185(4) 0.8931(7) 0.065(2) Uani 1 1 d . . . H38A H 0.7789 0.2664 0.8728 0.078 Uiso 1 1 calc R . . H38B H 0.7077 0.3187 0.9532 0.078 Uiso 1 1 calc R . . C39 C 0.6898(7) 0.3547(5) 0.7883(6) 0.068(2) Uani 1 1 d . . . H39A H 0.6772 0.4067 0.8063 0.101 Uiso 1 1 calc R . . H39B H 0.5987 0.3312 0.7611 0.101 Uiso 1 1 calc R . . H39C H 0.7416 0.3511 0.7253 0.101 Uiso 1 1 calc R . . C40 C 1.0832(5) 0.4144(3) 1.1890(5) 0.0329(11) Uani 1 1 d . . . H40A H 1.0337 0.4457 1.1220 0.039 Uiso 1 1 calc R . . H40B H 1.1750 0.4372 1.2220 0.039 Uiso 1 1 calc R . . C41 C 1.0005(6) 0.4141(3) 1.2866(5) 0.0427(14) Uani 1 1 d . . . H41A H 0.9205 0.3801 1.2632 0.051 Uiso 1 1 calc R . . H41B H 1.0605 0.3959 1.3624 0.051 Uiso 1 1 calc R . . C42 C 0.9479(6) 0.4910(3) 1.3062(6) 0.0492(15) Uani 1 1 d . . . H42A H 0.9258 0.4929 1.3860 0.059 Uiso 1 1 calc R . . H42B H 1.0228 0.5271 1.3059 0.059 Uiso 1 1 calc R . . C43 C 0.8204(6) 0.5130(4) 1.2125(6) 0.0579(18) Uani 1 1 d . . . H43A H 0.8416 0.5117 1.1332 0.087 Uiso 1 1 calc R . . H43B H 0.7922 0.5629 1.2291 0.087 Uiso 1 1 calc R . . H43C H 0.7445 0.4785 1.2142 0.087 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 0.0333(16) 0.0395(18) 0.0505(18) -0.0213(15) 0.0045(14) 0.0024(14) O1 0.0277(18) 0.036(2) 0.039(2) -0.0071(17) 0.0013(16) 0.0003(16) O2 0.047(2) 0.039(2) 0.055(2) -0.012(2) 0.021(2) 0.0011(19) N1 0.030(2) 0.025(2) 0.022(2) -0.0049(18) 0.0046(17) -0.0008(18) N2 0.026(2) 0.032(2) 0.027(2) -0.0081(18) 0.0053(17) -0.0016(18) N3 0.029(2) 0.028(2) 0.038(2) -0.0032(19) 0.0174(19) -0.0031(18) N4 0.035(2) 0.027(2) 0.033(2) -0.0045(19) 0.0128(19) -0.0006(18) N5 0.033(2) 0.028(2) 0.028(2) -0.0030(19) 0.0046(19) -0.0036(19) C1 0.043(3) 0.042(3) 0.034(3) 0.001(3) 0.001(2) 0.005(3) C2 0.028(3) 0.032(3) 0.024(2) 0.000(2) 0.007(2) -0.003(2) C3 0.029(3) 0.023(2) 0.035(3) 0.000(2) 0.009(2) -0.006(2) C4 0.041(3) 0.029(3) 0.041(3) 0.002(2) 0.013(2) 0.003(2) C5 0.023(2) 0.024(2) 0.029(2) -0.0018(19) 0.0118(19) -0.0074(19) C6 0.025(2) 0.033(3) 0.031(3) -0.008(2) 0.011(2) -0.008(2) C7 0.029(3) 0.045(3) 0.029(3) -0.014(2) 0.005(2) -0.012(2) C8 0.024(2) 0.041(3) 0.026(2) -0.002(2) 0.0037(19) -0.003(2) C9 0.015(2) 0.026(2) 0.032(2) -0.004(2) 0.0046(18) -0.0031(18) C10 0.022(2) 0.027(3) 0.025(2) -0.005(2) 0.0094(18) -0.0057(19) C11 0.022(2) 0.028(3) 0.041(3) -0.002(2) 0.011(2) 0.000(2) C12 0.024(2) 0.028(3) 0.045(3) 0.003(2) 0.015(2) 0.000(2) C13 0.023(3) 0.035(3) 0.056(3) 0.000(3) 0.007(2) 0.001(2) C14 0.028(3) 0.034(3) 0.067(4) -0.008(3) 0.013(3) 0.007(2) C15 0.035(3) 0.033(3) 0.061(4) -0.015(3) 0.022(3) -0.002(2) C16 0.032(3) 0.027(3) 0.045(3) -0.001(2) 0.018(2) -0.004(2) C17 0.038(3) 0.026(3) 0.042(3) -0.008(2) 0.019(2) -0.002(2) C18 0.045(3) 0.021(2) 0.025(2) 0.001(2) 0.014(2) -0.001(2) C19 0.053(3) 0.033(3) 0.032(3) 0.002(2) 0.015(3) 0.001(3) C20 0.071(4) 0.024(3) 0.027(3) -0.001(2) 0.012(3) 0.009(3) C21 0.058(4) 0.035(3) 0.023(3) 0.002(2) 0.000(2) -0.009(3) C22 0.049(3) 0.023(2) 0.027(3) 0.004(2) 0.005(2) -0.006(2) C23 0.039(3) 0.024(2) 0.024(2) 0.0024(19) 0.013(2) -0.005(2) C24 0.047(3) 0.048(4) 0.039(3) -0.001(3) 0.000(3) -0.012(3) C25 0.038(3) 0.025(3) 0.030(2) 0.004(2) 0.001(2) -0.002(2) C26 0.034(3) 0.026(3) 0.028(2) 0.004(2) 0.009(2) -0.003(2) C27 0.038(3) 0.032(3) 0.038(3) 0.001(2) 0.012(2) -0.001(2) N6 0.023(2) 0.025(2) 0.041(2) 0.0083(19) 0.0059(17) -0.0014(17) C28 0.025(2) 0.032(3) 0.032(3) 0.012(2) 0.006(2) -0.004(2) C29 0.033(3) 0.026(3) 0.034(3) 0.009(2) 0.006(2) -0.004(2) C30 0.033(3) 0.037(3) 0.025(2) 0.007(2) 0.003(2) -0.001(2) C31 0.040(3) 0.039(3) 0.034(3) -0.003(2) 0.004(2) 0.004(2) C32 0.033(3) 0.026(3) 0.040(3) 0.006(2) 0.011(2) -0.001(2) C33 0.029(3) 0.039(3) 0.044(3) 0.012(3) 0.013(2) 0.000(2) C34 0.038(3) 0.042(3) 0.035(3) 0.006(3) 0.014(2) 0.007(2) C35 0.054(4) 0.051(4) 0.038(3) 0.003(3) 0.008(3) 0.008(3) C36 0.020(2) 0.034(3) 0.050(3) 0.002(2) 0.004(2) -0.007(2) C37 0.038(3) 0.038(3) 0.050(4) 0.007(3) -0.002(3) -0.001(3) C38 0.035(3) 0.073(5) 0.076(5) 0.010(4) -0.009(3) -0.011(3) C39 0.056(4) 0.081(5) 0.065(5) 0.005(4) 0.011(4) -0.005(4) C40 0.027(2) 0.031(3) 0.043(3) 0.002(2) 0.010(2) -0.001(2) C41 0.038(3) 0.037(3) 0.056(4) 0.004(3) 0.016(3) -0.002(3) C42 0.050(4) 0.039(3) 0.067(4) -0.007(3) 0.033(3) -0.005(3) C43 0.054(4) 0.041(4) 0.090(5) 0.017(4) 0.039(4) 0.012(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 O1 C11 1.227(6) . ? O2 C17 1.230(6) . ? N1 C2 1.373(6) . ? N1 C10 1.376(6) . ? N2 C11 1.361(6) . ? N2 C9 1.413(6) . ? N3 C16 1.331(6) . ? N3 C12 1.343(6) . ? N4 C17 1.349(6) . ? N4 C18 1.418(6) . ? N5 C23 1.365(6) . ? N5 C26 1.374(6) . ? C1 C2 1.483(7) . ? C2 C3 1.370(7) . ? C3 C5 1.437(7) . ? C3 C4 1.499(7) . ? C5 C10 1.405(6) . ? C5 C6 1.410(6) . ? C6 C7 1.370(7) . ? C7 C8 1.398(7) . ? C8 C9 1.397(6) . ? C9 C10 1.407(6) . ? C11 C12 1.506(7) . ? C12 C13 1.391(7) . ? C13 C14 1.363(8) . ? C14 C15 1.384(8) . ? C15 C16 1.390(7) . ? C16 C17 1.512(7) . ? C18 C19 1.393(7) . ? C18 C23 1.415(7) . ? C19 C20 1.395(8) . ? C20 C21 1.380(8) . ? C21 C22 1.414(7) . ? C22 C23 1.410(7) . ? C22 C25 1.426(7) . ? C24 C25 1.503(7) . ? C25 C26 1.373(7) . ? C26 C27 1.492(7) . ? N6 C32 1.515(6) . ? N6 C36 1.519(6) . ? N6 C28 1.519(6) . ? N6 C40 1.521(6) . ? C28 C29 1.518(7) . ? C29 C30 1.512(7) . ? C30 C31 1.526(7) . ? C32 C33 1.529(7) . ? C33 C34 1.524(7) . ? C34 C35 1.524(8) . ? C36 C37 1.505(7) . ? C37 C38 1.529(8) . ? C38 C39 1.421(9) . ? C40 C41 1.531(7) . ? C41 C42 1.522(8) . ? C42 C43 1.509(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 C2 N1 C10 108.3(4) . . ? C11 N2 C9 125.8(4) . . ? C16 N3 C12 117.3(4) . . ? C17 N4 C18 125.5(4) . . ? C23 N5 C26 109.1(4) . . ? C3 C2 N1 110.3(4) . . ? C3 C2 C1 129.7(5) . . ? N1 C2 C1 120.0(4) . . ? C2 C3 C5 106.4(4) . . ? C2 C3 C4 128.0(5) . . ? C5 C3 C4 125.5(4) . . ? C10 C5 C6 119.8(4) . . ? C10 C5 C3 106.7(4) . . ? C6 C5 C3 133.5(5) . . ? C7 C6 C5 117.2(5) . . ? C6 C7 C8 123.4(4) . . ? C9 C8 C7 120.6(5) . . ? C8 C9 C10 116.4(4) . . ? C8 C9 N2 125.2(4) . . ? C10 C9 N2 118.4(4) . . ? N1 C10 C5 108.3(4) . . ? N1 C10 C9 129.1(4) . . ? C5 C10 C9 122.6(4) . . ? O1 C11 N2 125.5(5) . . ? O1 C11 C12 119.5(4) . . ? N2 C11 C12 115.0(4) . . ? N3 C12 C13 122.8(5) . . ? N3 C12 C11 118.1(4) . . ? C13 C12 C11 119.0(5) . . ? C14 C13 C12 119.0(5) . . ? C13 C14 C15 119.2(5) . . ? C14 C15 C16 118.3(5) . . ? N3 C16 C15 123.4(5) . . ? N3 C16 C17 118.5(4) . . ? C15 C16 C17 118.1(5) . . ? O2 C17 N4 124.2(5) . . ? O2 C17 C16 118.7(5) . . ? N4 C17 C16 117.0(4) . . ? C19 C18 C23 116.4(5) . . ? C19 C18 N4 124.0(5) . . ? C23 C18 N4 119.6(4) . . ? C18 C19 C20 120.8(5) . . ? C21 C20 C19 123.2(5) . . ? C20 C21 C22 117.6(5) . . ? C23 C22 C21 119.0(5) . . ? C23 C22 C25 107.2(4) . . ? C21 C22 C25 133.8(5) . . ? N5 C23 C22 107.6(4) . . ? N5 C23 C18 129.4(5) . . ? C22 C23 C18 122.9(4) . . ? C26 C25 C22 106.4(4) . . ? C26 C25 C24 128.1(5) . . ? C22 C25 C24 125.4(5) . . ? C25 C26 N5 109.6(4) . . ? C25 C26 C27 130.6(5) . . ? N5 C26 C27 119.6(4) . . ? C32 N6 C36 105.6(4) . . ? C32 N6 C28 111.1(4) . . ? C36 N6 C28 111.5(4) . . ? C32 N6 C40 111.4(4) . . ? C36 N6 C40 110.0(4) . . ? C28 N6 C40 107.2(4) . . ? C29 C28 N6 114.7(4) . . ? C30 C29 C28 111.8(4) . . ? C29 C30 C31 111.6(4) . . ? N6 C32 C33 114.2(4) . . ? C34 C33 C32 110.1(4) . . ? C35 C34 C33 111.5(5) . . ? C37 C36 N6 117.0(4) . . ? C36 C37 C38 109.2(5) . . ? C39 C38 C37 115.9(6) . . ? N6 C40 C41 114.8(4) . . ? C42 C41 C40 111.3(5) . . ? C43 C42 C41 113.2(5) . . ? 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 N2 H98 F1 0.92(5) 1.92(5) 2.795(5) 158(4) . N2 H98 N3 0.92(5) 2.23(5) 2.715(6) 112(4) . N5 H96 F1 0.86(5) 1.74(5) 2.573(5) 164(5) . N1 H99 F1 0.85(5) 1.75(6) 2.563(5) 159(5) . N4 H97 F1 0.87(6) 1.94(7) 2.788(5) 165(6) . _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.418 _refine_diff_density_min -0.267 _refine_diff_density_rms 0.058 #==END data_2007sot0046 _database_code_depnum_ccdc_archive 'CCDC 640965' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C31 H37 N5 O4 S2' _chemical_formula_weight 607.78 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 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 26.9646(10) _cell_length_b 9.8223(3) _cell_length_c 27.2375(10) _cell_angle_alpha 90.00 _cell_angle_beta 119.586(3) _cell_angle_gamma 90.00 _cell_volume 6273.4(4) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 11446 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Slab _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.287 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2576 _exptl_absorpt_coefficient_mu 0.213 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9191 _exptl_absorpt_correction_T_max 0.9831 _exptl_absorpt_process_details ; SADABS V2.10 (Sheldrick, G.M., 2003) ; _exptl_special_details ; SADABS was used to perform the Absorption correction Parameter refinement on 18692 reflections reduced R(int) from 0.0771 to 0.0456 Ratio of minimum to maximum apparent transmission: 0.755072 The given Tmin and Tmax were generated using the SHELX SIZE command ; _diffrn_ambient_temperature 120(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 CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \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 37226 _diffrn_reflns_av_R_equivalents 0.0784 _diffrn_reflns_av_sigmaI/netI 0.0691 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 27.48 _reflns_number_total 7183 _reflns_number_gt 4513 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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 position of the 1 DMSO oxygen is disordered over 2 sites ; _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^)+(0.1331P)^2^+19.8852P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0039(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 7183 _refine_ls_number_parameters 392 _refine_ls_number_restraints 510 _refine_ls_R_factor_all 0.1403 _refine_ls_R_factor_gt 0.0925 _refine_ls_wR_factor_ref 0.2748 _refine_ls_wR_factor_gt 0.2375 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.020 _refine_ls_shift/su_max 0.062 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.02144(12) 0.8197(3) -0.03379(12) 0.0507(7) Uani 1 1 d U . . O2 O 0.27258(13) 0.8305(3) 0.23089(11) 0.0519(8) Uani 1 1 d U . . N1 N 0.10584(14) 0.4065(3) -0.01054(13) 0.0375(7) Uani 1 1 d U . . H1 H 0.1210 0.4358 0.0245 0.045 Uiso 1 1 calc R . . N2 N 0.10392(14) 0.7070(3) -0.01240(12) 0.0386(7) Uani 1 1 d U . . H2 H 0.1405 0.7014 0.0125 0.046 Uiso 1 1 calc R . . N3 N 0.15604(14) 0.8034(3) 0.09161(12) 0.0351(7) Uani 1 1 d U . . N4 N 0.26251(13) 0.7097(3) 0.15501(12) 0.0368(7) Uani 1 1 d U . . H4 H 0.2405 0.6965 0.1185 0.044 Uiso 1 1 calc R . . N5 N 0.27217(13) 0.4090(3) 0.17052(12) 0.0344(7) Uani 1 1 d U . . H5 H 0.2357 0.4299 0.1516 0.041 Uiso 1 1 calc R . . C1 C 0.1110(4) 0.1633(5) 0.0153(3) 0.103(3) Uani 1 1 d U . . H1A H 0.1010 0.0746 -0.0036 0.155 Uiso 1 1 calc R . . H1B H 0.0893 0.1779 0.0349 0.155 Uiso 1 1 calc R . . H1C H 0.1519 0.1654 0.0427 0.155 Uiso 1 1 calc R . . C2 C 0.0972(2) 0.2725(4) -0.02730(19) 0.0562(12) Uani 1 1 d U . . C3 C 0.0737(2) 0.2641(5) -0.08500(18) 0.0521(11) Uani 1 1 d U . . C4 C 0.0559(3) 0.1378(6) -0.1209(3) 0.093(2) Uani 1 1 d U . . H4A H 0.0680 0.0572 -0.0965 0.140 Uiso 1 1 calc R . . H4B H 0.0738 0.1370 -0.1447 0.140 Uiso 1 1 calc R . . H4C H 0.0144 0.1370 -0.1449 0.140 Uiso 1 1 calc R . . C5 C 0.06659(15) 0.4003(4) -0.10509(15) 0.0389(9) Uani 1 1 d U . . C6 C 0.04213(17) 0.4591(5) -0.15912(16) 0.0508(11) Uani 1 1 d U . . H6 H 0.0280 0.4038 -0.1919 0.061 Uiso 1 1 calc R . . C7 C 0.0391(2) 0.5988(6) -0.16338(17) 0.0687(16) Uani 1 1 d U . . H7 H 0.0225 0.6392 -0.1998 0.082 Uiso 1 1 calc R . . C8 C 0.0596(2) 0.6834(5) -0.11605(18) 0.0647(14) Uani 1 1 d U . . H8 H 0.0575 0.7795 -0.1206 0.078 Uiso 1 1 calc R . . C9 C 0.08305(16) 0.6272(4) -0.06252(14) 0.0379(8) Uani 1 1 d U . . C10 C 0.08691(14) 0.4867(4) -0.05752(14) 0.0303(7) Uani 1 1 d U . . C11 C 0.07161(18) 0.7901(4) -0.00064(16) 0.0389(9) Uani 1 1 d U . . C12 C 0.10161(17) 0.8414(4) 0.05947(16) 0.0371(8) Uani 1 1 d U . . C13 C 0.07200(19) 0.9177(4) 0.07983(17) 0.0428(9) Uani 1 1 d U . . H13 H 0.0333 0.9426 0.0559 0.051 Uiso 1 1 calc R . . C14 C 0.10087(19) 0.9559(4) 0.13614(18) 0.0436(9) Uani 1 1 d U . . H14 H 0.0819 1.0076 0.1514 0.052 Uiso 1 1 calc R . . C15 C 0.15738(19) 0.9186(4) 0.17011(17) 0.0421(9) Uani 1 1 d U . . H15 H 0.1779 0.9446 0.2087 0.051 Uiso 1 1 calc R . . C16 C 0.18336(17) 0.8413(4) 0.14585(15) 0.0370(8) Uani 1 1 d U . . C17 C 0.24386(17) 0.7945(4) 0.18163(15) 0.0374(8) Uani 1 1 d U . . C18 C 0.31553(16) 0.6414(4) 0.18277(15) 0.0377(9) Uani 1 1 d U . . C19 C 0.3677(2) 0.7072(6) 0.20583(19) 0.0591(13) Uani 1 1 d U . . H19 H 0.3689 0.8034 0.2030 0.071 Uiso 1 1 calc R . . C20 C 0.41871(19) 0.6333(8) 0.2333(2) 0.0771(19) Uani 1 1 d U . . H20 H 0.4539 0.6811 0.2489 0.092 Uiso 1 1 calc R . . C21 C 0.41948(19) 0.4948(8) 0.23848(18) 0.0675(16) Uani 1 1 d U . . H21 H 0.4547 0.4470 0.2573 0.081 Uiso 1 1 calc R . . C22 C 0.36808(17) 0.4247(5) 0.21580(15) 0.0482(11) Uani 1 1 d U . . C23 C 0.31659(14) 0.5000(4) 0.18778(14) 0.0330(8) Uani 1 1 d U . . C24 C 0.3930(3) 0.1672(7) 0.2429(3) 0.095(2) Uani 1 1 d U . . H24A H 0.3723 0.0909 0.2477 0.142 Uiso 1 1 calc R . . H24B H 0.4241 0.1953 0.2799 0.142 Uiso 1 1 calc R . . H24C H 0.4088 0.1388 0.2189 0.142 Uiso 1 1 calc R . . C25 C 0.3524(2) 0.2860(5) 0.21539(17) 0.0552(12) Uani 1 1 d U . . C26 C 0.29416(19) 0.2795(4) 0.18772(18) 0.0471(10) Uani 1 1 d U . . C27 C 0.2546(3) 0.1631(5) 0.1764(2) 0.0681(15) Uani 1 1 d U . . H27A H 0.2767 0.0811 0.1948 0.102 Uiso 1 1 calc R . . H27B H 0.2321 0.1478 0.1356 0.102 Uiso 1 1 calc R . . H27C H 0.2291 0.1838 0.1914 0.102 Uiso 1 1 calc R . . S1 S 0.11845(4) 0.48831(11) 0.13561(4) 0.0450(3) Uani 1 1 d U . . O3 O 0.15235(10) 0.4486(3) 0.10748(10) 0.0378(6) Uani 1 1 d U . . C28 C 0.1021(2) 0.3346(6) 0.1586(2) 0.0647(14) Uani 1 1 d U . . H28A H 0.0830 0.2720 0.1266 0.097 Uiso 1 1 calc R . . H28B H 0.0769 0.3539 0.1741 0.097 Uiso 1 1 calc R . . H28C H 0.1374 0.2928 0.1879 0.097 Uiso 1 1 calc R . . C29 C 0.04863(19) 0.5221(5) 0.0803(2) 0.0579(12) Uani 1 1 d U . . H29A H 0.0496 0.5982 0.0575 0.087 Uiso 1 1 calc R . . H29B H 0.0242 0.5459 0.0963 0.087 Uiso 1 1 calc R . . H29C H 0.0334 0.4410 0.0565 0.087 Uiso 1 1 calc R . . S2 S 0.25097(10) 0.5231(2) 0.02180(6) 0.1131(9) Uani 1 1 d U . . O4A O 0.22209(12) 0.6237(3) 0.03865(11) 0.0322(7) Uani 0.823(4) 1 d PU . . O4B O 0.2577(6) 0.3712(14) 0.0325(5) 0.0322(7) Uani 0.177(4) 1 d PU . . C30 C 0.3171(3) 0.5367(15) 0.0512(4) 0.190(6) Uani 1 1 d U . . H30A H 0.3271 0.6091 0.0328 0.285 Uiso 1 1 calc R . . H30B H 0.3335 0.4504 0.0480 0.285 Uiso 1 1 calc R . . H30C H 0.3322 0.5592 0.0911 0.285 Uiso 1 1 calc R . . C31 C 0.2241(2) 0.5407(6) -0.05207(19) 0.0618(13) Uani 1 1 d U . . H31A H 0.1831 0.5215 -0.0723 0.093 Uiso 1 1 calc R . . H31B H 0.2438 0.4766 -0.0642 0.093 Uiso 1 1 calc R . . H31C H 0.2307 0.6339 -0.0604 0.093 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 0.0485(17) 0.0552(18) 0.0429(16) -0.0014(14) 0.0185(14) 0.0147(14) O2 0.067(2) 0.0558(18) 0.0300(14) -0.0103(13) 0.0214(14) -0.0007(15) N1 0.0517(19) 0.0342(16) 0.0291(15) -0.0055(13) 0.0219(14) -0.0066(14) N2 0.0455(18) 0.0373(17) 0.0278(15) -0.0002(13) 0.0140(14) 0.0104(14) N3 0.055(2) 0.0234(14) 0.0295(15) 0.0024(12) 0.0229(15) 0.0018(13) N4 0.0435(18) 0.0366(16) 0.0274(14) -0.0039(13) 0.0152(14) -0.0030(14) N5 0.0283(15) 0.0376(16) 0.0350(16) 0.0045(13) 0.0138(13) 0.0053(12) C1 0.227(9) 0.037(3) 0.075(4) -0.002(3) 0.096(5) -0.011(4) C2 0.096(4) 0.039(2) 0.047(2) -0.0093(19) 0.046(3) -0.016(2) C3 0.071(3) 0.051(2) 0.045(2) -0.021(2) 0.037(2) -0.023(2) C4 0.160(7) 0.064(3) 0.078(4) -0.040(3) 0.075(4) -0.043(4) C5 0.0300(18) 0.056(2) 0.0316(18) -0.0123(17) 0.0161(15) -0.0075(17) C6 0.035(2) 0.085(3) 0.0252(18) -0.015(2) 0.0096(16) 0.005(2) C7 0.081(4) 0.088(4) 0.0245(19) 0.008(2) 0.016(2) 0.044(3) C8 0.088(4) 0.068(3) 0.032(2) 0.014(2) 0.025(2) 0.037(3) C9 0.036(2) 0.049(2) 0.0239(16) 0.0006(15) 0.0116(15) 0.0107(17) C10 0.0240(16) 0.043(2) 0.0241(16) -0.0033(14) 0.0118(13) -0.0001(14) C11 0.053(2) 0.0306(18) 0.0383(19) 0.0077(16) 0.0266(19) 0.0074(17) C12 0.053(2) 0.0269(17) 0.0375(19) 0.0059(15) 0.0270(18) 0.0023(16) C13 0.058(3) 0.0337(19) 0.046(2) 0.0034(17) 0.033(2) 0.0048(17) C14 0.063(3) 0.0330(19) 0.047(2) -0.0039(17) 0.037(2) -0.0001(18) C15 0.067(3) 0.0311(19) 0.0361(19) -0.0011(16) 0.031(2) -0.0009(18) C16 0.056(2) 0.0272(17) 0.0341(18) 0.0010(14) 0.0272(18) -0.0008(16) C17 0.053(2) 0.0311(18) 0.0327(18) -0.0021(15) 0.0249(18) -0.0059(16) C18 0.039(2) 0.051(2) 0.0281(17) -0.0058(16) 0.0199(16) -0.0078(17) C19 0.053(3) 0.079(3) 0.057(3) -0.028(2) 0.035(2) -0.032(2) C20 0.029(2) 0.148(6) 0.058(3) -0.042(4) 0.025(2) -0.034(3) C21 0.028(2) 0.141(5) 0.031(2) -0.009(3) 0.0126(18) 0.005(3) C22 0.033(2) 0.089(3) 0.0254(18) 0.0087(19) 0.0165(16) 0.016(2) C23 0.0250(16) 0.052(2) 0.0203(15) 0.0003(15) 0.0099(13) -0.0005(15) C24 0.106(5) 0.126(5) 0.074(4) 0.058(4) 0.062(4) 0.087(4) C25 0.059(3) 0.077(3) 0.039(2) 0.023(2) 0.031(2) 0.035(2) C26 0.061(3) 0.044(2) 0.047(2) 0.0119(18) 0.035(2) 0.017(2) C27 0.107(4) 0.035(2) 0.082(4) 0.007(2) 0.061(3) 0.005(3) S1 0.0451(6) 0.0550(6) 0.0424(6) -0.0172(5) 0.0273(5) -0.0151(5) O3 0.0316(13) 0.0524(16) 0.0295(13) 0.0003(11) 0.0153(11) 0.0012(11) C28 0.056(3) 0.090(4) 0.044(2) 0.021(2) 0.022(2) -0.009(3) C29 0.048(2) 0.051(3) 0.087(4) 0.017(2) 0.043(3) 0.006(2) S2 0.1517(17) 0.1237(14) 0.0439(7) 0.0033(8) 0.0329(9) 0.0977(13) O4A 0.0322(15) 0.0414(16) 0.0245(13) -0.0100(12) 0.0152(12) 0.0003(12) O4B 0.0322(15) 0.0414(16) 0.0245(13) -0.0100(12) 0.0152(12) 0.0003(12) C30 0.063(5) 0.374(17) 0.109(7) -0.019(9) 0.025(5) 0.066(8) C31 0.054(3) 0.092(4) 0.043(2) -0.015(2) 0.026(2) 0.007(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 O1 C11 1.234(5) . ? O2 C17 1.224(4) . ? N1 C10 1.369(4) . ? N1 C2 1.375(5) . ? N2 C11 1.343(5) . ? N2 C9 1.427(5) . ? N3 C16 1.338(5) . ? N3 C12 1.338(5) . ? N4 C17 1.353(5) . ? N4 C18 1.414(5) . ? N5 C23 1.378(5) . ? N5 C26 1.384(5) . ? C1 C2 1.486(7) . ? C2 C3 1.377(6) . ? C3 C5 1.421(6) . ? C3 C4 1.504(6) . ? C5 C6 1.406(6) . ? C5 C10 1.414(5) . ? C6 C7 1.376(7) . ? C7 C8 1.398(7) . ? C8 C9 1.386(5) . ? C9 C10 1.385(5) . ? C11 C12 1.510(5) . ? C12 C13 1.394(5) . ? C13 C14 1.386(6) . ? C14 C15 1.386(6) . ? C15 C16 1.400(5) . ? C16 C17 1.501(6) . ? C18 C19 1.384(6) . ? C18 C23 1.395(6) . ? C19 C20 1.401(8) . ? C20 C21 1.368(9) . ? C21 C22 1.389(7) . ? C22 C23 1.418(5) . ? C22 C25 1.425(7) . ? C24 C25 1.521(6) . ? C25 C26 1.367(6) . ? C26 C27 1.488(7) . ? S1 O3 1.505(3) . ? S1 C29 1.767(5) . ? S1 C28 1.771(5) . ? S2 O4A 1.466(3) . ? S2 O4B 1.513(14) . ? S2 C30 1.558(8) . ? S2 C31 1.779(5) . ? 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 C10 N1 C2 108.5(3) . . ? C11 N2 C9 124.5(3) . . ? C16 N3 C12 118.2(3) . . ? C17 N4 C18 123.4(3) . . ? C23 N5 C26 109.0(3) . . ? N1 C2 C3 110.0(4) . . ? N1 C2 C1 119.7(4) . . ? C3 C2 C1 130.2(4) . . ? C2 C3 C5 106.4(3) . . ? C2 C3 C4 127.6(5) . . ? C5 C3 C4 125.9(4) . . ? C6 C5 C10 118.8(4) . . ? C6 C5 C3 134.0(4) . . ? C10 C5 C3 107.1(3) . . ? C7 C6 C5 118.4(4) . . ? C6 C7 C8 122.3(4) . . ? C9 C8 C7 120.1(5) . . ? C10 C9 C8 118.2(4) . . ? C10 C9 N2 118.6(3) . . ? C8 C9 N2 123.2(4) . . ? N1 C10 C9 129.8(3) . . ? N1 C10 C5 107.9(3) . . ? C9 C10 C5 122.1(3) . . ? O1 C11 N2 125.1(4) . . ? O1 C11 C12 121.4(3) . . ? N2 C11 C12 113.5(3) . . ? N3 C12 C13 123.2(4) . . ? N3 C12 C11 116.3(3) . . ? C13 C12 C11 120.3(4) . . ? C14 C13 C12 117.8(4) . . ? C13 C14 C15 119.9(4) . . ? C14 C15 C16 118.0(4) . . ? N3 C16 C15 122.8(4) . . ? N3 C16 C17 117.5(3) . . ? C15 C16 C17 119.8(3) . . ? O2 C17 N4 124.3(4) . . ? O2 C17 C16 121.3(3) . . ? N4 C17 C16 114.4(3) . . ? C19 C18 C23 116.9(4) . . ? C19 C18 N4 123.6(4) . . ? C23 C18 N4 119.4(3) . . ? C18 C19 C20 120.7(5) . . ? C21 C20 C19 122.1(4) . . ? C20 C21 C22 119.1(5) . . ? C21 C22 C23 118.6(5) . . ? C21 C22 C25 134.8(5) . . ? C23 C22 C25 106.6(4) . . ? N5 C23 C18 129.8(3) . . ? N5 C23 C22 107.5(4) . . ? C18 C23 C22 122.6(4) . . ? C26 C25 C22 107.7(4) . . ? C26 C25 C24 126.0(5) . . ? C22 C25 C24 126.2(5) . . ? C25 C26 N5 109.1(4) . . ? C25 C26 C27 131.3(4) . . ? N5 C26 C27 119.5(4) . . ? O3 S1 C29 105.9(2) . . ? O3 S1 C28 106.2(2) . . ? C29 S1 C28 96.6(2) . . ? O4A S2 O4B 129.5(5) . . ? O4A S2 C30 115.6(5) . . ? O4B S2 C30 89.3(7) . . ? O4A S2 C31 107.8(2) . . ? O4B S2 C31 104.9(5) . . ? C30 S2 C31 107.2(4) . . ? 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 1.99 2.846(4) 164.2 . N2 H2 O4A 0.88 2.09 2.895(4) 150.9 . N4 H4 O4A 0.88 2.10 2.922(4) 154.3 . N5 H5 O3 0.88 1.97 2.839(4) 171.9 . N5 H5 S1 0.88 3.03 3.847(3) 156.2 . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.238 _refine_diff_density_min -1.454 _refine_diff_density_rms 0.108 #==END data_2007sot0069 _database_code_depnum_ccdc_archive 'CCDC 640966' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H62 Cl N5 O2' _chemical_formula_weight 728.44 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' Cl Cl 0.1484 0.1585 '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 11.6862(3) _cell_length_b 13.0971(3) _cell_length_c 14.2217(3) _cell_angle_alpha 98.8110(10) _cell_angle_beta 94.7230(10) _cell_angle_gamma 101.2830(10) _cell_volume 2095.16(7) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 27796 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Block _exptl_crystal_colour 'Pale Yellow' _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.155 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 788 _exptl_absorpt_coefficient_mu 0.132 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9148 _exptl_absorpt_correction_T_max 0.9740 _exptl_absorpt_process_details ; SADABS V2.10 (Sheldrick, G.M., 2003) ; _exptl_special_details ; SADABS was used to perform the Absorption correction Parameter refinement on 18345 reflections reduced R(int) from 0.0749 to 0.0386 Ratio of minimum to maximum apparent transmission: 0.807839 The given Tmin and Tmax were generated using the SHELX SIZE command ; _diffrn_ambient_temperature 120(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 CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \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 28340 _diffrn_reflns_av_R_equivalents 0.0452 _diffrn_reflns_av_sigmaI/netI 0.0615 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 27.48 _reflns_number_total 9550 _reflns_number_gt 6561 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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. ; _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^)+(0.0585P)^2^+0.6730P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9550 _refine_ls_number_parameters 473 _refine_ls_number_restraints 20 _refine_ls_R_factor_all 0.0881 _refine_ls_R_factor_gt 0.0525 _refine_ls_wR_factor_ref 0.1413 _refine_ls_wR_factor_gt 0.1250 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 9.074 _refine_ls_shift/su_max 0.031 _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 Cl1 Cl 1.58182(4) 0.20750(4) 0.35823(4) 0.03010(15) Uani 1 1 d . . . C1 C 1.9358(2) 0.4018(2) 0.37550(17) 0.0433(8) Uani 1 1 d . . . H1A H 1.9714 0.3414 0.3835 0.065 Uiso 1 1 calc R . . H1B H 1.8747 0.4054 0.4184 0.065 Uiso 1 1 calc R . . H1C H 1.9963 0.4671 0.3911 0.065 Uiso 1 1 calc R . . C2 C 1.88245(19) 0.38882(18) 0.27412(16) 0.0320(7) Uani 1 1 d . . . C3 C 1.9234(2) 0.43214(18) 0.19872(17) 0.0340(7) Uani 1 1 d . . . C4 C 2.0377(2) 0.5085(2) 0.19866(19) 0.0479(9) Uani 1 1 d . . . H4A H 2.0742 0.5348 0.2647 0.072 Uiso 1 1 calc R . . H4B H 2.0229 0.5680 0.1688 0.072 Uiso 1 1 calc R . . H4C H 2.0905 0.4725 0.1624 0.072 Uiso 1 1 calc R . . C5 C 1.83636(19) 0.39100(17) 0.11747(16) 0.0315(7) Uani 1 1 d . . . C6 C 1.8305(2) 0.40353(19) 0.02126(17) 0.0366(7) Uani 1 1 d . . . H6 H 1.8930 0.4477 -0.0013 0.044 Uiso 1 1 calc R . . C7 C 1.7321(2) 0.35050(18) -0.04004(16) 0.0365(7) Uani 1 1 d . . . H7 H 1.7274 0.3589 -0.1053 0.044 Uiso 1 1 calc R . . C8 C 1.6388(2) 0.28443(17) -0.00845(15) 0.0318(7) Uani 1 1 d . . . H8 H 1.5720 0.2498 -0.0525 0.038 Uiso 1 1 calc R . . C9 C 1.64249(18) 0.26876(16) 0.08610(15) 0.0265(6) Uani 1 1 d . . . C10 C 1.74284(18) 0.32308(16) 0.14853(15) 0.0277(6) Uani 1 1 d . . . C11 C 1.45986(18) 0.12829(16) 0.07121(15) 0.0257(6) Uani 1 1 d . . . C12 C 1.37074(18) 0.07856(16) 0.12967(14) 0.0248(6) Uani 1 1 d . . . C13 C 1.31377(19) -0.02653(17) 0.09852(16) 0.0293(6) Uani 1 1 d . . . H13 H 1.3330 -0.0651 0.0420 0.035 Uiso 1 1 calc R . . C14 C 1.22925(19) -0.07524(17) 0.14941(16) 0.0310(7) Uani 1 1 d . . . H14 H 1.1909 -0.1470 0.1277 0.037 Uiso 1 1 calc R . . C15 C 1.20044(19) -0.01929(17) 0.23210(16) 0.0298(6) Uani 1 1 d . . . H15 H 1.1422 -0.0528 0.2667 0.036 Uiso 1 1 calc R . . C16 C 1.25673(18) 0.08591(16) 0.26438(15) 0.0268(6) Uani 1 1 d . . . C17 C 1.34109(18) 0.13460(16) 0.21243(14) 0.0254(6) Uani 1 1 d . . . H17 H 1.3787 0.2066 0.2336 0.031 Uiso 1 1 calc R . . C18 C 1.22128(18) 0.14336(17) 0.35348(15) 0.0274(6) Uani 1 1 d . . . C19 C 1.29766(19) 0.28874(16) 0.49276(15) 0.0274(6) Uani 1 1 d . . . C20 C 1.1925(2) 0.29448(17) 0.53042(16) 0.0323(7) Uani 1 1 d . . . H20 H 1.1210 0.2511 0.4980 0.039 Uiso 1 1 calc R . . C21 C 1.1909(2) 0.36386(18) 0.61597(17) 0.0369(7) Uani 1 1 d . . . H21 H 1.1179 0.3664 0.6401 0.044 Uiso 1 1 calc R . . C22 C 1.2917(2) 0.42820(18) 0.66582(17) 0.0356(7) Uani 1 1 d . . . H22 H 1.2886 0.4744 0.7235 0.043 Uiso 1 1 calc R . . C23 C 1.3989(2) 0.42427(16) 0.62983(15) 0.0301(6) Uani 1 1 d . . . C24 C 1.40012(19) 0.35512(16) 0.54297(15) 0.0276(6) Uani 1 1 d . . . C25 C 1.5566(3) 0.5570(2) 0.75238(19) 0.0493(9) Uani 1 1 d . . . H25A H 1.5440 0.5216 0.8077 0.074 Uiso 1 1 calc R . . H25B H 1.5108 0.6123 0.7538 0.074 Uiso 1 1 calc R . . H25C H 1.6402 0.5888 0.7547 0.074 Uiso 1 1 calc R . . C26 C 1.5178(2) 0.47789(17) 0.66187(16) 0.0335(7) Uani 1 1 d . . . C27 C 1.5861(2) 0.44229(17) 0.59592(16) 0.0319(7) Uani 1 1 d . . . C28 C 1.7150(2) 0.46991(19) 0.59069(18) 0.0399(8) Uani 1 1 d . . . H28A H 1.7507 0.5314 0.6399 0.060 Uiso 1 1 calc R . . H28B H 1.7293 0.4866 0.5273 0.060 Uiso 1 1 calc R . . H28C H 1.7499 0.4098 0.6015 0.060 Uiso 1 1 calc R . . C29 C 0.78968(12) 0.02617(14) 0.19957(11) 0.0322(7) Uani 1 1 d . A . H29A H 0.7361 -0.0001 0.1394 0.039 Uiso 1 1 calc R . . H29B H 0.7707 0.0932 0.2297 0.039 Uiso 1 1 calc R . . C30 C 0.9144(2) 0.05005(19) 0.17425(17) 0.0399(7) Uani 1 1 d . . . H30A H 0.9699 0.0730 0.2337 0.048 Uiso 1 1 calc R . . H30B H 0.9327 -0.0147 0.1386 0.048 Uiso 1 1 calc R . . C31 C 0.9294(2) 0.1362(2) 0.11361(18) 0.0454(8) Uani 1 1 d . . . H31A H 0.8723 0.1127 0.0552 0.054 Uiso 1 1 calc R . . H31B H 0.9099 0.2000 0.1500 0.054 Uiso 1 1 calc R . . C32 C 1.0499(3) 0.1659(3) 0.0839(2) 0.0846(12) Uani 1 1 d . . . H32A H 1.1054 0.2014 0.1403 0.127 Uiso 1 1 calc R . . H32B H 1.0488 0.2136 0.0373 0.127 Uiso 1 1 calc R . . H32C H 1.0745 0.1020 0.0549 0.127 Uiso 1 1 calc R . . C33 C 0.83952(19) -0.01647(17) 0.36279(16) 0.0319(7) Uani 1 1 d D A . H33A H 0.8188 -0.0703 0.4038 0.038 Uiso 1 1 calc R . . H33B H 0.9228 -0.0126 0.3522 0.038 Uiso 1 1 calc R . . C34 C 0.8283(2) 0.08971(18) 0.41679(16) 0.0353(7) Uani 1 1 d D . . H34A H 0.7442 0.0918 0.4181 0.042 Uiso 1 1 calc R . . H34B H 0.8647 0.1468 0.3836 0.042 Uiso 1 1 calc R . . C35 C 0.8886(2) 0.10761(19) 0.51901(16) 0.0371(7) Uani 1 1 d D . . H35A H 0.8531 0.0493 0.5512 0.045 Uiso 1 1 calc R . . H35B H 0.9728 0.1062 0.5171 0.045 Uiso 1 1 calc R . . C36 C 0.8778(2) 0.2124(2) 0.57681(18) 0.0452(8) Uani 1 1 d D . . H36A H 0.9172 0.2706 0.5475 0.068 Uiso 1 1 calc R . . H36B H 0.9146 0.2192 0.6426 0.068 Uiso 1 1 calc R . . H36C H 0.7946 0.2148 0.5776 0.068 Uiso 1 1 calc R . . C37A C 0.6335(4) -0.0650(3) 0.2849(3) 0.0384(5) Uani 0.554(3) 1 d PD A 1 H37A H 0.6181 0.0070 0.3003 0.046 Uiso 0.554(3) 1 calc PR A 1 H37B H 0.5842 -0.0999 0.2243 0.046 Uiso 0.554(3) 1 calc PR A 1 C38A C 0.5909(3) -0.1262(3) 0.3645(3) 0.0384(5) Uani 0.554(3) 1 d PD A 1 H38A H 0.6142 -0.1955 0.3554 0.046 Uiso 0.554(3) 1 calc PR A 1 H38B H 0.6288 -0.0860 0.4277 0.046 Uiso 0.554(3) 1 calc PR A 1 C39A C 0.4575(3) -0.1435(3) 0.3624(3) 0.0384(5) Uani 0.554(3) 1 d PD A 1 H39A H 0.4347 -0.1655 0.4230 0.046 Uiso 0.554(3) 1 calc PR A 1 H39B H 0.4334 -0.0758 0.3584 0.046 Uiso 0.554(3) 1 calc PR A 1 C40A C 0.3926(4) -0.2264(3) 0.2789(3) 0.0384(5) Uani 0.554(3) 1 d PD A 1 H40A H 0.4096 -0.2023 0.2186 0.058 Uiso 0.554(3) 1 calc PR A 1 H40B H 0.3080 -0.2375 0.2831 0.058 Uiso 0.554(3) 1 calc PR A 1 H40C H 0.4184 -0.2929 0.2810 0.058 Uiso 0.554(3) 1 calc PR A 1 C37B C 0.63527(14) -0.0681(2) 0.26895(15) 0.0384(5) Uani 0.446(3) 1 d PD A 2 H37C H 0.5964 -0.0791 0.2026 0.046 Uiso 0.446(3) 1 calc PR A 2 H37D H 0.6183 -0.0026 0.3043 0.046 Uiso 0.446(3) 1 calc PR A 2 C38B C 0.5834(4) -0.1605(4) 0.3158(4) 0.0384(5) Uani 0.446(3) 1 d PD A 2 H38C H 0.6289 -0.1556 0.3789 0.046 Uiso 0.446(3) 1 calc PR A 2 H38D H 0.5882 -0.2277 0.2752 0.046 Uiso 0.446(3) 1 calc PR A 2 C39B C 0.4551(4) -0.1593(4) 0.3291(4) 0.0384(5) Uani 0.446(3) 1 d PD A 2 H39C H 0.4135 -0.1572 0.2661 0.046 Uiso 0.446(3) 1 calc PR A 2 H39D H 0.4195 -0.2270 0.3483 0.046 Uiso 0.446(3) 1 calc PR A 2 C40B C 0.43282(16) -0.07341(5) 0.39841(5) 0.0384(5) Uani 0.446(3) 1 d PD A 2 H40D H 0.4683 -0.0772 0.4624 0.058 Uiso 0.446(3) 1 calc PR A 2 H40E H 0.3479 -0.0798 0.3987 0.058 Uiso 0.446(3) 1 calc PR A 2 H40F H 0.4673 -0.0055 0.3808 0.058 Uiso 0.446(3) 1 calc PR A 2 C41 C 0.7932(2) -0.15943(18) 0.22540(19) 0.0427(8) Uani 1 1 d . A . H41A H 0.8784 -0.1478 0.2196 0.051 Uiso 1 1 calc R . . H41B H 0.7764 -0.2084 0.2715 0.051 Uiso 1 1 calc R . . C42 C 0.7266(3) -0.2120(2) 0.1286(2) 0.0660(10) Uani 1 1 d . . . H42A H 0.6412 -0.2257 0.1341 0.079 Uiso 1 1 calc R . . H42B H 0.7425 -0.1635 0.0821 0.079 Uiso 1 1 calc R . . C43 C 0.7610(3) -0.3152(2) 0.0917(2) 0.0552(9) Uani 1 1 d . . . H43A H 0.7451 -0.3640 0.1380 0.066 Uiso 1 1 calc R . . H43B H 0.8463 -0.3018 0.0857 0.066 Uiso 1 1 calc R . . C44 C 0.6926(3) -0.3661(2) -0.0052(2) 0.0801(12) Uani 1 1 d . . . H44A H 0.6086 -0.3835 0.0015 0.120 Uiso 1 1 calc R . . H44B H 0.7189 -0.4309 -0.0293 0.120 Uiso 1 1 calc R . . H44C H 0.7063 -0.3168 -0.0505 0.120 Uiso 1 1 calc R . . N1 N 1.77302(16) 0.32202(14) 0.24413(13) 0.0295(5) Uani 1 1 d D . . H1 H 1.7301 0.2851 0.2803 0.035 Uiso 1 1 calc R . . N2 N 1.55102(15) 0.20304(13) 0.12244(12) 0.0267(5) Uani 1 1 d . . . H2 H 1.5533 0.2114 0.1852 0.032 Uiso 1 1 calc R . . N3 N 1.30728(15) 0.22096(14) 0.40680(12) 0.0286(5) Uani 1 1 d . . . H3 H 1.3766 0.2302 0.3857 0.034 Uiso 1 1 calc R . . N4 N 1.51487(16) 0.36758(14) 0.52363(13) 0.0301(5) Uani 1 1 d . . . H4 H 1.5395 0.3337 0.4735 0.036 Uiso 1 1 calc R . . N5 N 0.76417(16) -0.05392(14) 0.26641(14) 0.0333(6) Uani 1 1 d . . . O1 O 1.44916(13) 0.10234(12) -0.01648(10) 0.0305(4) Uani 1 1 d . . . O2 O 1.12093(14) 0.11952(13) 0.37511(11) 0.0380(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0258(2) 0.0382(2) 0.0275(2) 0.0055(2) 0.0039(2) 0.0096(2) C1 0.0343(13) 0.0552(14) 0.0379(12) 0.0145(11) -0.0013(11) 0.0004(11) C2 0.0241(10) 0.0359(11) 0.0350(11) 0.0071(10) 0.0019(9) 0.0034(9) C3 0.0262(11) 0.0379(11) 0.0367(11) 0.0085(10) 0.0040(9) 0.0026(9) C4 0.0331(13) 0.0602(16) 0.0464(13) 0.0161(12) 0.0019(11) -0.0039(12) C5 0.0280(10) 0.0327(10) 0.0351(11) 0.0076(9) 0.0071(9) 0.0071(9) C6 0.0371(12) 0.0386(12) 0.0350(11) 0.0117(10) 0.0099(10) 0.0040(10) C7 0.0436(13) 0.0395(12) 0.0270(10) 0.0099(10) 0.0077(10) 0.0054(10) C8 0.0342(11) 0.0316(10) 0.0287(10) 0.0043(9) 0.0032(9) 0.0058(9) C9 0.0269(10) 0.0255(9) 0.0284(10) 0.0034(8) 0.0062(8) 0.0088(8) C10 0.0271(10) 0.0297(10) 0.0293(10) 0.0062(9) 0.0069(8) 0.0109(8) C11 0.0258(9) 0.0263(9) 0.0262(10) 0.0015(8) 0.0018(8) 0.0112(7) C12 0.0213(9) 0.0286(9) 0.0243(9) 0.0028(8) -0.0007(8) 0.0076(8) C13 0.0293(10) 0.0302(10) 0.0279(10) 0.0001(9) 0.0023(9) 0.0096(8) C14 0.0300(11) 0.0267(10) 0.0333(11) 0.0000(9) -0.0006(9) 0.0046(9) C15 0.0255(10) 0.0323(10) 0.0300(10) 0.0046(9) 0.0016(9) 0.0034(9) C16 0.0247(10) 0.0312(10) 0.0240(9) 0.0025(8) -0.0011(8) 0.0084(8) C17 0.0221(9) 0.0270(9) 0.0260(10) 0.0016(8) 0.0008(8) 0.0054(8) C18 0.0251(10) 0.0314(10) 0.0255(9) 0.0049(9) 0.0032(8) 0.0054(8) C19 0.0296(10) 0.0282(10) 0.0242(9) 0.0030(8) 0.0027(9) 0.0068(8) C20 0.0297(11) 0.0326(11) 0.0332(11) 0.0012(10) 0.0064(9) 0.0059(9) C21 0.0375(11) 0.0359(11) 0.0377(12) 0.0010(10) 0.0138(10) 0.0091(9) C22 0.0454(12) 0.0292(10) 0.0311(11) -0.0013(9) 0.0095(10) 0.0082(9) C23 0.0381(11) 0.0255(9) 0.0274(10) 0.0040(9) 0.0027(9) 0.0091(8) C24 0.0285(10) 0.0282(10) 0.0271(10) 0.0058(9) 0.0033(9) 0.0076(8) C25 0.0565(16) 0.0360(13) 0.0458(14) -0.0097(12) -0.0028(13) 0.0031(12) C26 0.0390(12) 0.0279(10) 0.0311(11) 0.0011(9) -0.0029(10) 0.0070(9) C27 0.0332(11) 0.0270(10) 0.0331(11) 0.0038(9) -0.0060(10) 0.0054(9) C28 0.0331(12) 0.0374(12) 0.0447(13) 0.0015(11) -0.0074(11) 0.0058(10) C29 0.0325(11) 0.0330(10) 0.0317(11) 0.0047(9) -0.0041(9) 0.0122(8) C30 0.0404(12) 0.0506(12) 0.0359(12) 0.0106(10) 0.0085(10) 0.0226(9) C31 0.0423(13) 0.0595(14) 0.0401(12) 0.0169(11) 0.0038(11) 0.0189(11) C32 0.0729(17) 0.120(2) 0.0966(18) 0.0700(16) 0.0506(15) 0.0490(15) C33 0.0270(10) 0.0387(11) 0.0313(11) 0.0082(9) -0.0016(9) 0.0103(9) C34 0.0322(11) 0.0416(11) 0.0341(11) 0.0074(10) 0.0003(10) 0.0137(9) C35 0.0379(12) 0.0411(12) 0.0325(11) 0.0104(10) 0.0063(10) 0.0045(10) C36 0.0424(13) 0.0524(14) 0.0383(12) 0.0036(12) 0.0116(11) 0.0047(12) C37A 0.0333(7) 0.0370(7) 0.0450(9) 0.0112(7) 0.0013(7) 0.0059(6) C38A 0.0333(7) 0.0370(7) 0.0450(9) 0.0112(7) 0.0013(7) 0.0059(6) C39A 0.0333(7) 0.0370(7) 0.0450(9) 0.0112(7) 0.0013(7) 0.0059(6) C40A 0.0333(7) 0.0370(7) 0.0450(9) 0.0112(7) 0.0013(7) 0.0059(6) C37B 0.0333(7) 0.0370(7) 0.0450(9) 0.0112(7) 0.0013(7) 0.0059(6) C38B 0.0333(7) 0.0370(7) 0.0450(9) 0.0112(7) 0.0013(7) 0.0059(6) C39B 0.0333(7) 0.0370(7) 0.0450(9) 0.0112(7) 0.0013(7) 0.0059(6) C40B 0.0333(7) 0.0370(7) 0.0450(9) 0.0112(7) 0.0013(7) 0.0059(6) C41 0.0439(12) 0.0314(10) 0.0522(14) 0.0011(11) -0.0100(12) 0.0175(9) C42 0.0731(17) 0.0383(12) 0.0766(19) -0.0154(14) -0.0370(15) 0.0264(11) C43 0.0743(17) 0.0404(12) 0.0515(15) 0.0028(12) -0.0080(14) 0.0239(11) C44 0.104(2) 0.0513(15) 0.075(2) -0.0190(16) -0.0295(19) 0.0318(15) N1 0.0262(9) 0.0337(9) 0.0289(8) 0.0095(7) 0.0045(7) 0.0035(7) N2 0.0275(8) 0.0298(8) 0.0215(8) 0.0017(7) 0.0042(7) 0.0045(7) N3 0.0232(8) 0.0352(9) 0.0246(8) -0.0016(8) 0.0043(7) 0.0046(7) N4 0.0281(9) 0.0336(9) 0.0271(9) 0.0007(8) 0.0007(7) 0.0076(7) N5 0.0294(9) 0.0285(8) 0.0415(10) 0.0059(8) -0.0054(8) 0.0089(7) O1 0.0324(7) 0.0353(7) 0.0232(7) 0.0011(6) 0.0021(6) 0.0089(6) O2 0.0278(8) 0.0445(9) 0.0361(8) -0.0021(7) 0.0089(7) -0.0007(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.494(3) . ? C2 C3 1.366(3) . ? C2 N1 1.393(3) . ? C3 C5 1.436(3) . ? C3 C4 1.504(3) . ? C5 C6 1.401(3) . ? C5 C10 1.414(3) . ? C6 C7 1.378(3) . ? C7 C8 1.403(3) . ? C8 C9 1.389(3) . ? C9 C10 1.406(3) . ? C9 N2 1.421(3) . ? C10 N1 1.379(3) . ? C11 O1 1.231(2) . ? C11 N2 1.367(2) . ? C11 C12 1.498(3) . ? C12 C13 1.393(3) . ? C12 C17 1.395(3) . ? C13 C14 1.385(3) . ? C14 C15 1.390(3) . ? C15 C16 1.394(3) . ? C16 C17 1.394(3) . ? C16 C18 1.503(3) . ? C18 O2 1.230(3) . ? C18 N3 1.363(2) . ? C19 C20 1.391(3) . ? C19 C24 1.400(3) . ? C19 N3 1.423(3) . ? C20 C21 1.406(3) . ? C21 C22 1.375(3) . ? C22 C23 1.399(4) . ? C23 C24 1.418(3) . ? C23 C26 1.431(3) . ? C24 N4 1.375(3) . ? C25 C26 1.499(3) . ? C26 C27 1.366(3) . ? C27 N4 1.392(2) . ? C27 C28 1.490(3) . ? C29 C30 1.515(3) . ? C29 N5 1.524(3) . ? C30 C31 1.514(4) . ? C31 C32 1.499(4) . ? C33 C34 1.517(3) . ? C33 N5 1.524(3) . ? C34 C35 1.525(3) . ? C35 C36 1.521(4) . ? C37A C38A 1.544(6) . ? C37A N5 1.553(5) . ? C38A C39A 1.528(6) . ? C39A C40A 1.516(5) . ? C37B N5 1.485(3) . ? C37B C38B 1.517(6) . ? C38B C39B 1.529(7) . ? C39B C40B 1.458(5) . ? C41 C42 1.516(4) . ? C41 N5 1.528(3) . ? C42 C43 1.515(4) . ? C43 C44 1.521(4) . ? 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 C3 C2 N1 109.34(19) . . ? C3 C2 C1 130.9(2) . . ? N1 C2 C1 119.8(2) . . ? C2 C3 C5 107.11(19) . . ? C2 C3 C4 127.4(2) . . ? C5 C3 C4 125.5(2) . . ? C6 C5 C10 119.32(19) . . ? C6 C5 C3 133.4(2) . . ? C10 C5 C3 107.2(2) . . ? C7 C6 C5 118.7(2) . . ? C6 C7 C8 121.7(2) . . ? C9 C8 C7 121.20(19) . . ? C8 C9 C10 117.02(19) . . ? C8 C9 N2 123.88(17) . . ? C10 C9 N2 119.10(19) . . ? N1 C10 C9 130.6(2) . . ? N1 C10 C5 107.35(17) . . ? C9 C10 C5 122.1(2) . . ? O1 C11 N2 123.88(19) . . ? O1 C11 C12 121.03(16) . . ? N2 C11 C12 115.10(17) . . ? C13 C12 C17 119.22(19) . . ? C13 C12 C11 118.49(18) . . ? C17 C12 C11 122.27(17) . . ? C14 C13 C12 120.5(2) . . ? C13 C14 C15 120.09(19) . . ? C14 C15 C16 120.2(2) . . ? C17 C16 C15 119.40(19) . . ? C17 C16 C18 122.47(17) . . ? C15 C16 C18 118.11(19) . . ? C16 C17 C12 120.61(18) . . ? O2 C18 N3 123.78(19) . . ? O2 C18 C16 120.77(17) . . ? N3 C18 C16 115.45(18) . . ? C20 C19 C24 117.27(19) . . ? C20 C19 N3 124.33(17) . . ? C24 C19 N3 118.40(19) . . ? C19 C20 C21 120.63(19) . . ? C22 C21 C20 122.1(2) . . ? C21 C22 C23 118.7(2) . . ? C22 C23 C24 119.11(18) . . ? C22 C23 C26 133.7(2) . . ? C24 C23 C26 107.2(2) . . ? N4 C24 C19 130.56(19) . . ? N4 C24 C23 107.22(17) . . ? C19 C24 C23 122.2(2) . . ? C27 C26 C23 107.29(18) . . ? C27 C26 C25 127.9(2) . . ? C23 C26 C25 124.8(2) . . ? C26 C27 N4 109.12(19) . . ? C26 C27 C28 131.58(19) . . ? N4 C27 C28 119.3(2) . . ? C30 C29 N5 116.04(17) . . ? C31 C30 C29 110.4(2) . . ? C32 C31 C30 114.9(3) . . ? C34 C33 N5 115.68(19) . . ? C33 C34 C35 110.2(2) . . ? C36 C35 C34 112.2(2) . . ? C38A C37A N5 118.2(3) . . ? C39A C38A C37A 110.8(4) . . ? C40A C39A C38A 112.8(4) . . ? N5 C37B C38B 113.3(3) . . ? C37B C38B C39B 109.8(4) . . ? C40B C39B C38B 117.1(3) . . ? C42 C41 N5 114.9(2) . . ? C43 C42 C41 112.0(3) . . ? C42 C43 C44 110.8(3) . . ? C10 N1 C2 108.99(18) . . ? C11 N2 C9 127.54(18) . . ? C18 N3 C19 127.37(18) . . ? C24 N4 C27 109.22(18) . . ? C37B N5 C33 115.88(17) . . ? C37B N5 C29 103.02(17) . . ? C33 N5 C29 111.45(14) . . ? C37B N5 C41 109.36(17) . . ? C33 N5 C41 105.83(18) . . ? C29 N5 C41 111.41(17) . . ? C37B N5 C37A 8.22(17) . . ? C33 N5 C37A 107.7(2) . . ? C29 N5 C37A 107.9(2) . . ? C41 N5 C37A 112.6(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 Cl1 0.88 2.29 3.1474(19) 165.5 . N2 H2 Cl1 0.88 2.47 3.3334(18) 168.8 . N3 H3 Cl1 0.88 2.53 3.3690(19) 160.3 . N4 H4 Cl1 0.88 2.30 3.1582(19) 165.2 . _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.717 _refine_diff_density_min -0.682 _refine_diff_density_rms 0.049 #==END data_2007sot0185 _database_code_depnum_ccdc_archive 'CCDC 640967' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H62 F N5 O2' _chemical_formula_weight 711.99 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.7830(4) _cell_length_b 18.6247(5) _cell_length_c 11.3671(5) _cell_angle_alpha 90.00 _cell_angle_beta 102.697(2) _cell_angle_gamma 90.00 _cell_volume 2020.50(13) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 22421 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Fragment _exptl_crystal_colour 'Pale Yellow' _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.170 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 772 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9649 _exptl_absorpt_correction_T_max 0.9851 _exptl_absorpt_process_details ; SADABS V2.10 (Sheldrick, G.M., 2003) ; _exptl_special_details ; SADABS was used to perform the Absorption correction Parameter refinement on 17584 reflections reduced R(int) from 0.1192 to 0.0580 Ratio of minimum to maximum apparent transmission: 0.704956 The given Tmin and Tmax were generated using the SHELX SIZE command ; _diffrn_ambient_temperature 120(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 CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \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 27652 _diffrn_reflns_av_R_equivalents 0.0818 _diffrn_reflns_av_sigmaI/netI 0.0670 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.11 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4764 _reflns_number_gt 3511 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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. ; _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^)+(0.0585P)^2^+0.1060P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.1466(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4764 _refine_ls_number_parameters 474 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.0915 _refine_ls_R_factor_gt 0.0605 _refine_ls_wR_factor_ref 0.1339 _refine_ls_wR_factor_gt 0.1233 _refine_ls_goodness_of_fit_ref 1.198 _refine_ls_restrained_S_all 1.224 _refine_ls_shift/su_max 0.133 _refine_ls_shift/su_mean 0.003 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 1.19547(4) 0.450378(19) 1.31722(3) 0.05527(12) Uani 1 1 d . . . O2 O 0.96224(3) 0.261517(17) 0.76027(3) 0.04334(10) Uani 1 1 d . . . N1 N 1.60528(4) 0.298562(18) 1.26093(3) 0.03384(11) Uani 1 1 d . . . H1 H 1.5420 0.2826 1.1991 0.041 Uiso 1 1 calc R . . N2 N 1.32882(4) 0.356602(19) 1.27968(3) 0.03607(11) Uani 1 1 d . . . H2 H 1.3268 0.3170 1.2371 0.043 Uiso 1 1 calc R . . N3 N 1.15515(4) 0.220254(19) 0.89451(3) 0.03642(11) Uani 1 1 d . . . H3 H 1.2144 0.2313 0.9622 0.044 Uiso 1 1 calc R . . N4 N 1.36716(4) 0.117271(19) 1.01699(3) 0.03275(10) Uani 1 1 d . . . H4 H 1.3629 0.1531 1.0665 0.039 Uiso 1 1 calc R . . C1 C 1.80492(5) 0.24560(3) 1.18853(4) 0.04404(15) Uani 1 1 d . . . H1A H 1.8032 0.2764 1.1183 0.066 Uiso 1 1 calc R . . H1B H 1.7475 0.2028 1.1636 0.066 Uiso 1 1 calc R . . H1C H 1.9016 0.2310 1.2233 0.066 Uiso 1 1 calc R . . C2 C 1.74775(5) 0.28608(2) 1.28059(4) 0.03675(13) Uani 1 1 d . . . C3 C 1.81509(5) 0.31792(2) 1.38605(4) 0.03985(14) Uani 1 1 d . . . C4 C 1.96846(5) 0.31912(3) 1.44129(5) 0.05195(17) Uani 1 1 d . . . H4A H 2.0168 0.2848 1.3992 0.078 Uiso 1 1 calc R . . H4B H 1.9838 0.3059 1.5266 0.078 Uiso 1 1 calc R . . H4C H 2.0054 0.3675 1.4343 0.078 Uiso 1 1 calc R . . C5 C 1.70813(5) 0.35277(2) 1.43446(4) 0.03807(14) Uani 1 1 d . . . C6 C 1.71060(6) 0.39542(3) 1.53662(4) 0.04530(15) Uani 1 1 d . . . H6 H 1.7961 0.4048 1.5928 0.054 Uiso 1 1 calc R . . C7 C 1.58524(6) 0.42355(3) 1.55362(4) 0.04706(16) Uani 1 1 d . . . H7 H 1.5858 0.4518 1.6234 0.056 Uiso 1 1 calc R . . C8 C 1.45775(5) 0.41183(3) 1.47154(4) 0.04321(15) Uani 1 1 d . . . H8 H 1.3744 0.4328 1.4859 0.052 Uiso 1 1 calc R . . C9 C 1.45180(5) 0.36962(2) 1.36871(4) 0.03536(13) Uani 1 1 d . . . C10 C 1.57838(5) 0.33986(2) 1.35315(4) 0.03303(12) Uani 1 1 d . . . C11 C 1.21213(5) 0.39966(2) 1.25309(4) 0.03867(13) Uani 1 1 d . . . C12 C 1.10478(5) 0.38303(2) 1.14091(4) 0.03818(13) Uani 1 1 d . . . C13 C 0.97987(5) 0.42175(3) 1.11832(5) 0.04749(15) Uani 1 1 d . . . H13 H 0.9630 0.4556 1.1760 0.057 Uiso 1 1 calc R . . C14 C 0.88068(5) 0.41145(3) 1.01326(5) 0.05112(16) Uani 1 1 d . . . H14 H 0.7960 0.4382 0.9990 0.061 Uiso 1 1 calc R . . C15 C 0.90378(5) 0.36195(3) 0.92759(5) 0.04365(15) Uani 1 1 d . . . H15 H 0.8357 0.3554 0.8547 0.052 Uiso 1 1 calc R . . C16 C 1.02766(5) 0.32209(2) 0.94970(4) 0.03666(13) Uani 1 1 d . . . C17 C 1.12729(5) 0.33330(2) 1.05595(4) 0.03787(13) Uani 1 1 d . . . H17 H 1.2120 0.3066 1.0707 0.045 Uiso 1 1 calc R . . C18 C 1.04555(4) 0.26568(2) 0.85881(4) 0.03545(13) Uani 1 1 d . . . C19 C 1.18543(4) 0.15717(2) 0.83565(4) 0.03314(12) Uani 1 1 d . . . C20 C 1.12245(5) 0.13637(3) 0.71887(4) 0.03846(14) Uani 1 1 d . . . H20 H 1.0546 0.1666 0.6703 0.046 Uiso 1 1 calc R . . C21 C 1.15868(5) 0.07047(3) 0.67179(4) 0.04091(14) Uani 1 1 d . . . H21 H 1.1127 0.0574 0.5921 0.049 Uiso 1 1 calc R . . C22 C 1.25671(5) 0.02480(2) 0.73562(4) 0.03705(13) Uani 1 1 d . . . H22 H 1.2782 -0.0194 0.7019 0.044 Uiso 1 1 calc R . . C23 C 1.32510(4) 0.04536(2) 0.85335(4) 0.03233(12) Uani 1 1 d . . . C24 C 1.28840(4) 0.11033(2) 0.90146(4) 0.02992(11) Uani 1 1 d . . . C25 C 1.50511(5) -0.05680(3) 0.93260(5) 0.04594(15) Uani 1 1 d . . . H25A H 1.5780 -0.0652 1.0055 0.069 Uiso 1 1 calc R . . H25B H 1.5479 -0.0546 0.8624 0.069 Uiso 1 1 calc R . . H25C H 1.4370 -0.0961 0.9221 0.069 Uiso 1 1 calc R . . C26 C 1.43223(5) 0.01291(2) 0.94444(4) 0.03399(12) Uani 1 1 d . . . C27 C 1.45388(5) 0.05849(2) 1.04181(4) 0.03409(12) Uani 1 1 d . . . C28 C 1.55276(5) 0.05150(3) 1.16126(4) 0.04282(15) Uani 1 1 d . . . H28A H 1.5927 0.0986 1.1873 0.064 Uiso 1 1 calc R . . H28B H 1.6282 0.0182 1.1545 0.064 Uiso 1 1 calc R . . H28C H 1.5024 0.0331 1.2205 0.064 Uiso 1 1 calc R . . N5 N 1.60062(4) 0.16059(2) 1.64018(3) 0.03817(11) Uani 1 1 d D . . C29 C 1.58754(5) 0.23627(3) 1.69059(4) 0.04183(14) Uani 1 1 d . A . H29A H 1.6828 0.2559 1.7209 0.050 Uiso 1 1 calc R . . H29B H 1.5392 0.2676 1.6240 0.050 Uiso 1 1 calc R . . C30 C 1.50819(5) 0.23926(3) 1.79198(5) 0.05386(17) Uani 1 1 d . . . H30A H 1.4297 0.2045 1.7749 0.065 Uiso 1 1 calc R A . H30B H 1.5718 0.2250 1.8687 0.065 Uiso 1 1 calc R . . C31 C 1.45108(6) 0.31350(3) 1.80562(6) 0.0703(2) Uani 1 1 d . A . H31A H 1.4287 0.3173 1.8862 0.084 Uiso 1 1 calc R . . H31B H 1.5247 0.3493 1.8018 0.084 Uiso 1 1 calc R . . C32 C 1.32285(7) 0.33141(4) 1.71169(7) 0.0902(2) Uani 1 1 d . . . H32A H 1.3461 0.3320 1.6321 0.135 Uiso 1 1 calc R A . H32B H 1.2881 0.3788 1.7287 0.135 Uiso 1 1 calc R . . H32C H 1.2504 0.2952 1.7127 0.135 Uiso 1 1 calc R . . C33 C 1.64463(5) 0.10694(3) 1.74250(4) 0.04471(15) Uani 1 1 d . A . H33A H 1.5712 0.1057 1.7901 0.054 Uiso 1 1 calc R . . H33B H 1.6488 0.0586 1.7071 0.054 Uiso 1 1 calc R . . C34 C 1.78446(5) 0.12207(3) 1.82761(4) 0.04542(15) Uani 1 1 d . . . H34A H 1.7894 0.1734 1.8511 0.055 Uiso 1 1 calc R A . H34B H 1.8614 0.1122 1.7861 0.055 Uiso 1 1 calc R . . C35 C 1.80211(5) 0.07541(3) 1.93988(4) 0.04803(16) Uani 1 1 d . A . H35A H 1.7936 0.0243 1.9157 0.058 Uiso 1 1 calc R . . H35B H 1.7262 0.0864 1.9821 0.058 Uiso 1 1 calc R . . C36 C 1.94346(6) 0.08748(3) 2.02590(5) 0.05633(18) Uani 1 1 d . . . H36A H 2.0188 0.0757 1.9849 0.084 Uiso 1 1 calc R A . H36B H 1.9508 0.0566 2.0968 0.084 Uiso 1 1 calc R . . H36C H 1.9516 0.1379 2.0513 0.084 Uiso 1 1 calc R . . C37 C 1.71046(4) 0.16483(2) 1.56379(4) 0.03590(13) Uani 1 1 d D A . H37A H 1.6778 0.1992 1.4971 0.043 Uiso 1 1 calc R . . H37B H 1.7984 0.1841 1.6142 0.043 Uiso 1 1 calc R . . C38 C 1.74168(5) 0.09378(2) 1.51095(4) 0.04336(15) Uani 1 1 d D . . H38A H 1.6529 0.0722 1.4664 0.052 Uiso 1 1 calc R A . H38B H 1.7835 0.0607 1.5773 0.052 Uiso 1 1 calc R . . C39 C 1.84095(5) 0.10165(2) 1.42646(4) 0.04178(15) Uani 1 1 d D A . H39A H 1.9262 0.1274 1.4685 0.050 Uiso 1 1 calc R . . H39B H 1.7954 0.1307 1.3558 0.050 Uiso 1 1 calc R . . C40 C 1.88220(6) 0.02938(3) 1.38370(5) 0.05451(18) Uani 1 1 d D . . H40A H 1.9301 0.0010 1.4533 0.082 Uiso 1 1 calc R A . H40B H 1.9452 0.0365 1.3285 0.082 Uiso 1 1 calc R . . H40C H 1.7980 0.0038 1.3417 0.082 Uiso 1 1 calc R . . C41A C 1.46144(9) 0.13609(5) 1.57673(8) 0.05125(10) Uani 0.50 1 d PD A 3 H41A H 1.3954 0.1453 1.6297 0.061 Uiso 0.50 1 calc PR A 3 H41B H 1.4659 0.0834 1.5664 0.061 Uiso 0.50 1 calc PR A 3 C42A C 1.39967(8) 0.16862(6) 1.45458(8) 0.05125(10) Uani 0.50 1 d PD A 3 H42A H 1.4612 0.1586 1.3980 0.061 Uiso 0.50 1 calc PR A 3 H42B H 1.3911 0.2213 1.4619 0.061 Uiso 0.50 1 calc PR A 3 C43A C 1.25448(9) 0.13513(5) 1.40724(8) 0.05125(10) Uani 0.50 1 d PD A 3 H43A H 1.2636 0.0823 1.4023 0.061 Uiso 0.50 1 calc PR A 3 H43B H 1.1933 0.1458 1.4638 0.061 Uiso 0.50 1 calc PR A 3 C44A C 1.18925(10) 0.16479(6) 1.28408(8) 0.05125(10) Uani 0.50 1 d PD A 3 H44A H 1.1836 0.2172 1.2886 0.077 Uiso 0.50 1 calc PR A 3 H44B H 1.0949 0.1449 1.2566 0.077 Uiso 0.50 1 calc PR A 3 H44C H 1.2470 0.1515 1.2271 0.077 Uiso 0.50 1 calc PR A 3 C41B C 1.46288(9) 0.13598(5) 1.56070(8) 0.05125(10) Uani 0.50 1 d PD A 4 H41C H 1.3901 0.1376 1.6089 0.061 Uiso 0.50 1 calc PR A 4 H41D H 1.4733 0.0852 1.5383 0.061 Uiso 0.50 1 calc PR A 4 C42B C 1.41067(8) 0.17883(5) 1.44569(8) 0.05125(10) Uani 0.50 1 d PD A 4 H42C H 1.4676 0.1661 1.3867 0.061 Uiso 0.50 1 calc PR A 4 H42D H 1.4247 0.2306 1.4642 0.061 Uiso 0.50 1 calc PR A 4 C43B C 1.25592(9) 0.16572(5) 1.38825(9) 0.05125(10) Uani 0.50 1 d PD A 4 H43C H 1.2006 0.1705 1.4510 0.061 Uiso 0.50 1 calc PR A 4 H43D H 1.2233 0.2031 1.3266 0.061 Uiso 0.50 1 calc PR A 4 C44B C 1.22849(11) 0.09296(5) 1.33018(9) 0.05125(10) Uani 0.50 1 d PD A 4 H44D H 1.2929 0.0849 1.2765 0.077 Uiso 0.50 1 calc PR A 4 H44E H 1.1316 0.0907 1.2835 0.077 Uiso 0.50 1 calc PR A 4 H44F H 1.2431 0.0558 1.3928 0.077 Uiso 0.50 1 calc PR A 4 F1 F 1.38070(3) 0.243760(15) 1.11778(3) 0.05551(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0544(2) 0.04353(17) 0.0681(2) -0.02198(15) 0.01390(17) 0.00353(15) O2 0.03110(15) 0.04963(19) 0.04606(17) -0.00071(15) 0.00152(13) 0.00024(14) N1 0.03953(18) 0.03080(18) 0.03151(17) -0.00191(14) 0.00848(14) -0.00364(15) N2 0.04208(19) 0.02653(17) 0.04185(19) -0.00637(15) 0.01412(15) -0.00308(15) N3 0.03092(18) 0.03925(19) 0.03828(19) -0.00718(16) 0.00582(15) 0.00073(15) N4 0.03256(17) 0.03312(17) 0.03303(17) -0.00852(15) 0.00818(14) -0.00339(15) C1 0.0473(2) 0.0418(2) 0.0444(2) -0.0006(2) 0.0130(2) 0.0021(2) C2 0.0424(2) 0.0296(2) 0.0398(2) 0.00539(18) 0.01234(18) 0.00050(18) C3 0.0414(2) 0.0356(2) 0.0417(2) 0.0071(2) 0.00723(19) -0.0024(2) C4 0.0468(3) 0.0513(3) 0.0545(3) 0.0019(2) 0.0041(2) -0.0085(2) C5 0.0497(2) 0.0289(2) 0.0350(2) 0.00555(18) 0.00786(19) -0.00346(19) C6 0.0622(3) 0.0380(2) 0.0327(2) -0.0024(2) 0.0041(2) -0.0085(2) C7 0.0679(3) 0.0375(2) 0.0347(2) -0.00700(19) 0.0092(2) -0.0012(2) C8 0.0568(3) 0.0334(2) 0.0414(2) -0.0017(2) 0.0149(2) 0.0015(2) C9 0.0455(2) 0.0285(2) 0.0337(2) 0.00069(17) 0.01227(17) -0.00384(18) C10 0.0454(2) 0.02498(19) 0.02972(19) -0.00040(16) 0.01037(17) -0.00567(17) C11 0.0432(2) 0.0293(2) 0.0483(2) -0.00527(19) 0.02052(17) -0.00025(19) C12 0.0346(2) 0.0311(2) 0.0533(2) -0.00425(18) 0.01935(17) -0.00387(17) C13 0.0405(2) 0.0396(2) 0.0662(3) -0.0121(2) 0.0199(2) 0.0026(2) C14 0.0328(2) 0.0443(3) 0.0771(3) -0.0057(3) 0.0140(2) 0.0053(2) C15 0.0313(2) 0.0376(2) 0.0623(3) -0.0013(2) 0.0107(2) 0.00100(19) C16 0.0347(2) 0.0311(2) 0.0459(2) 0.00044(19) 0.01254(17) -0.00113(18) C17 0.0338(2) 0.0361(2) 0.0457(2) -0.00049(19) 0.01306(18) 0.00024(18) C18 0.02538(19) 0.0366(2) 0.0449(2) 0.00181(19) 0.00877(17) -0.00205(17) C19 0.02676(19) 0.0368(2) 0.0380(2) -0.00629(18) 0.01177(16) -0.00485(17) C20 0.0275(2) 0.0514(3) 0.0356(2) -0.0048(2) 0.00483(18) -0.00323(19) C21 0.0308(2) 0.0556(3) 0.0356(2) -0.0112(2) 0.00576(18) -0.0079(2) C22 0.0349(2) 0.0377(2) 0.0409(2) -0.01453(18) 0.01323(17) -0.01087(18) C23 0.03131(19) 0.0332(2) 0.0357(2) -0.00527(17) 0.01443(15) -0.00976(16) C24 0.02577(18) 0.0357(2) 0.03043(19) -0.00659(17) 0.01080(15) -0.00675(16) C25 0.0523(3) 0.0374(2) 0.0494(3) -0.0071(2) 0.0139(2) 0.0010(2) C26 0.0339(2) 0.0296(2) 0.0401(2) -0.00437(18) 0.01178(17) -0.00475(17) C27 0.0377(2) 0.0299(2) 0.0360(2) -0.00131(17) 0.01113(17) 0.00017(18) C28 0.0478(3) 0.0422(2) 0.0375(2) -0.0006(2) 0.0074(2) 0.0068(2) N5 0.02830(17) 0.03564(18) 0.0495(2) 0.00713(17) 0.00632(15) -0.00310(15) C29 0.0319(2) 0.0387(2) 0.0558(3) 0.0031(2) 0.01163(19) -0.00221(19) C30 0.0421(2) 0.0581(3) 0.0656(3) 0.0007(3) 0.0209(2) -0.0031(2) C31 0.0672(3) 0.0522(3) 0.1032(4) -0.0185(3) 0.0439(3) -0.0099(3) C32 0.0860(3) 0.0586(3) 0.1465(5) 0.0382(3) 0.0701(3) 0.0302(3) C33 0.0373(2) 0.0452(2) 0.0547(3) 0.0164(2) 0.01667(19) -0.0002(2) C34 0.0353(2) 0.0538(3) 0.0502(2) 0.0162(2) 0.01609(18) 0.0027(2) C35 0.0487(3) 0.0552(3) 0.0448(2) 0.0091(2) 0.02023(19) 0.0028(2) C36 0.0592(3) 0.0658(3) 0.0449(3) 0.0066(3) 0.0136(2) 0.0058(3) C37 0.0290(2) 0.0337(2) 0.0443(2) 0.00817(19) 0.00647(18) -0.00436(18) C38 0.0435(2) 0.0365(2) 0.0499(3) 0.0088(2) 0.0101(2) -0.0048(2) C39 0.0430(3) 0.0440(2) 0.0349(2) 0.0055(2) 0.0009(2) -0.0025(2) C40 0.0623(3) 0.0532(3) 0.0437(3) -0.0077(2) 0.0023(3) 0.0027(3) C41A 0.03635(14) 0.05489(18) 0.05894(18) 0.00032(15) 0.00277(14) -0.01010(14) C42A 0.03635(14) 0.05489(18) 0.05894(18) 0.00032(15) 0.00277(14) -0.01010(14) C43A 0.03635(14) 0.05489(18) 0.05894(18) 0.00032(15) 0.00277(14) -0.01010(14) C44A 0.03635(14) 0.05489(18) 0.05894(18) 0.00032(15) 0.00277(14) -0.01010(14) C41B 0.03635(14) 0.05489(18) 0.05894(18) 0.00032(15) 0.00277(14) -0.01010(14) C42B 0.03635(14) 0.05489(18) 0.05894(18) 0.00032(15) 0.00277(14) -0.01010(14) C43B 0.03635(14) 0.05489(18) 0.05894(18) 0.00032(15) 0.00277(14) -0.01010(14) C44B 0.03635(14) 0.05489(18) 0.05894(18) 0.00032(15) 0.00277(14) -0.01010(14) F1 0.04585(15) 0.04514(14) 0.06747(17) -0.02564(13) -0.00502(14) 0.00889(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C11 1.2259(6) . ? O2 C18 1.2344(5) . ? N1 C10 1.3715(6) . ? N1 C2 1.3819(6) . ? N2 C11 1.3733(6) . ? N2 C9 1.4125(5) . ? N3 C18 1.3561(5) . ? N3 C19 1.4153(6) . ? N4 C24 1.3749(5) . ? N4 C27 1.3757(5) . ? C1 C2 1.4945(7) . ? C2 C3 1.3695(6) . ? C3 C5 1.4395(7) . ? C3 C4 1.4939(7) . ? C5 C6 1.4028(7) . ? C5 C10 1.4168(6) . ? C6 C7 1.3857(8) . ? C7 C8 1.4007(7) . ? C8 C9 1.3992(7) . ? C9 C10 1.4029(7) . ? C11 C12 1.4954(6) . ? C12 C17 1.3902(7) . ? C12 C13 1.3933(7) . ? C13 C14 1.3767(7) . ? C14 C15 1.3949(8) . ? C15 C16 1.3962(6) . ? C16 C17 1.3909(6) . ? C16 C18 1.5104(7) . ? C19 C20 1.3901(6) . ? C19 C24 1.4156(6) . ? C20 C21 1.4149(7) . ? C21 C22 1.3651(6) . ? C22 C23 1.4113(6) . ? C23 C24 1.4066(6) . ? C23 C26 1.4349(6) . ? C25 C26 1.5015(7) . ? C26 C27 1.3739(6) . ? C27 C28 1.4896(6) . ? N5 C41A 1.4665(9) . ? N5 C41B 1.5188(9) . ? N5 C33 1.5220(6) . ? N5 C37 1.5249(6) . ? N5 C29 1.5373(6) . ? C29 C30 1.5256(8) . ? C30 C31 1.5118(8) . ? C31 C32 1.4954(9) . ? C33 C34 1.5181(6) . ? C34 C35 1.5222(7) . ? C35 C36 1.5246(7) . ? C37 C38 1.5120(6) . ? C38 C39 1.5156(7) . ? C39 C40 1.5157(7) . ? C41A C42A 1.5137(12) . ? C42A C43A 1.5363(12) . ? C43A C44A 1.5098(12) . ? C41B C42B 1.5210(13) . ? C42B C43B 1.5308(11) . ? C43B C44B 1.5055(13) . ? 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 C10 N1 C2 109.08(3) . . ? C11 N2 C9 126.40(4) . . ? C18 N3 C19 127.61(3) . . ? C24 N4 C27 108.18(3) . . ? C3 C2 N1 110.05(4) . . ? C3 C2 C1 130.49(4) . . ? N1 C2 C1 119.40(4) . . ? C2 C3 C5 106.23(4) . . ? C2 C3 C4 128.31(5) . . ? C5 C3 C4 125.44(4) . . ? C6 C5 C10 119.08(5) . . ? C6 C5 C3 133.63(4) . . ? C10 C5 C3 107.25(4) . . ? C7 C6 C5 118.35(4) . . ? C6 C7 C8 122.28(5) . . ? C9 C8 C7 120.76(5) . . ? C8 C9 C10 116.84(4) . . ? C8 C9 N2 124.58(4) . . ? C10 C9 N2 118.57(4) . . ? N1 C10 C9 129.86(4) . . ? N1 C10 C5 107.39(4) . . ? C9 C10 C5 122.67(4) . . ? O1 C11 N2 122.13(4) . . ? O1 C11 C12 120.42(4) . . ? N2 C11 C12 117.44(4) . . ? C17 C12 C13 118.90(4) . . ? C17 C12 C11 122.79(4) . . ? C13 C12 C11 118.24(4) . . ? C14 C13 C12 120.67(5) . . ? C13 C14 C15 120.42(5) . . ? C14 C15 C16 119.55(4) . . ? C17 C16 C15 119.43(4) . . ? C17 C16 C18 122.27(4) . . ? C15 C16 C18 118.25(4) . . ? C12 C17 C16 121.02(4) . . ? O2 C18 N3 123.60(4) . . ? O2 C18 C16 120.78(4) . . ? N3 C18 C16 115.60(4) . . ? C20 C19 N3 126.01(4) . . ? C20 C19 C24 116.58(4) . . ? N3 C19 C24 117.41(4) . . ? C19 C20 C21 120.51(4) . . ? C22 C21 C20 122.99(4) . . ? C21 C22 C23 117.79(4) . . ? C24 C23 C22 119.59(4) . . ? C24 C23 C26 106.87(3) . . ? C22 C23 C26 133.54(4) . . ? N4 C24 C23 108.35(3) . . ? N4 C24 C19 129.14(4) . . ? C23 C24 C19 122.51(4) . . ? C27 C26 C23 106.25(4) . . ? C27 C26 C25 127.91(4) . . ? C23 C26 C25 125.84(4) . . ? C26 C27 N4 110.34(4) . . ? C26 C27 C28 129.38(4) . . ? N4 C27 C28 120.28(4) . . ? C41A N5 C41B 6.85(5) . . ? C41A N5 C33 104.34(5) . . ? C41B N5 C33 108.75(5) . . ? C41A N5 C37 115.49(5) . . ? C41B N5 C37 108.72(5) . . ? C33 N5 C37 110.65(3) . . ? C41A N5 C29 108.92(5) . . ? C41B N5 C29 111.27(5) . . ? C33 N5 C29 110.48(4) . . ? C37 N5 C29 106.95(3) . . ? C30 C29 N5 114.39(4) . . ? C31 C30 C29 111.82(5) . . ? C32 C31 C30 113.69(5) . . ? C34 C33 N5 115.41(4) . . ? C33 C34 C35 110.40(4) . . ? C34 C35 C36 111.92(5) . . ? C38 C37 N5 114.21(4) . . ? C37 C38 C39 112.36(4) . . ? C38 C39 C40 111.72(4) . . ? N5 C41A C42A 117.83(8) . . ? C41A C42A C43A 108.11(8) . . ? C44A C43A C42A 110.24(8) . . ? N5 C41B C42B 116.06(7) . . ? C41B C42B C43B 113.38(8) . . ? C44B C43B C42B 113.25(8) . . ? 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 1.80 2.6353(4) 158.7 . N2 H2 F1 0.88 2.07 2.9106(5) 159.0 . N3 H3 F1 0.88 2.14 3.0066(4) 170.0 . N4 H4 F1 0.88 1.78 2.6102(5) 155.9 . _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.458 _refine_diff_density_min -0.438 _refine_diff_density_rms 0.119 #==END