# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Duncan Bruce' 'Peter N Horton' 'H Loc Nguyen' 'Carsten Prasang' 'Adrian C Whitwood' _publ_contact_author_name 'Duncan Bruce' _publ_contact_author_email DB519@YORK.AC.UK _publ_section_title ; Trimeric liquid crystals assembled using both hydrogen and halogen bonding ; # Attachment 'Cif1.cif' data_dwb0711a _database_code_depnum_ccdc_archive 'CCDC 694375' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C19 H23 N O), C6 H F4 I O' _chemical_formula_sum 'C44 H47 F4 I N2 O3' _chemical_formula_weight 854.74 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.4105(10) _cell_length_b 10.9417(11) _cell_length_c 19.4274(19) _cell_angle_alpha 75.531(2) _cell_angle_beta 78.768(2) _cell_angle_gamma 66.626(2) _cell_volume 1955.5(3) _cell_formula_units_Z 2 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 8311 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 28.30 _exptl_crystal_description Needle _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.452 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 876 _exptl_absorpt_coefficient_mu 0.880 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.650 _exptl_absorpt_correction_T_max 0.950 _exptl_absorpt_process_details 'SADABS v2.03; (Sheldrick)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19211 _diffrn_reflns_av_R_equivalents 0.0281 _diffrn_reflns_av_sigmaI/netI 0.0456 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.09 _diffrn_reflns_theta_max 28.31 _reflns_number_total 9443 _reflns_number_gt 7907 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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. Hydrogen H1 was placed as O-H rather than N+-H based upon difference map. A riding model was used for this hydrogen ; _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^)+(0.0539P)^2^+4.6007P] 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 9443 _refine_ls_number_parameters 489 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0579 _refine_ls_R_factor_gt 0.0442 _refine_ls_wR_factor_ref 0.1320 _refine_ls_wR_factor_gt 0.1159 _refine_ls_goodness_of_fit_ref 1.117 _refine_ls_restrained_S_all 1.117 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1421(4) 0.6558(4) 0.13389(17) 0.0207(7) Uani 1 1 d . . . C2 C 0.2352(4) 0.6896(4) 0.0782(2) 0.0265(8) Uani 1 1 d . . . C3 C 0.1902(4) 0.7732(4) 0.0149(2) 0.0257(8) Uani 1 1 d . . . C4 C 0.0496(4) 0.8280(4) 0.0023(2) 0.0236(7) Uani 1 1 d . . . C5 C -0.0437(4) 0.7941(4) 0.0590(2) 0.0237(7) Uani 1 1 d . . . C6 C 0.0026(4) 0.7091(4) 0.1225(2) 0.0227(7) Uani 1 1 d . . . F1 F 0.3734(2) 0.6404(3) 0.08589(13) 0.0367(6) Uani 1 1 d . . . F2 F 0.2848(3) 0.8037(3) -0.03675(14) 0.0424(7) Uani 1 1 d . . . F3 F -0.1824(2) 0.8463(3) 0.05088(13) 0.0319(5) Uani 1 1 d . . . F4 F -0.0955(2) 0.6812(3) 0.17372(12) 0.0305(5) Uani 1 1 d . . . I1 I 0.21674(3) 0.52536(3) 0.229044(13) 0.02488(8) Uani 1 1 d . . . O1 O 0.0145(3) 0.9058(3) -0.06008(15) 0.0312(6) Uani 1 1 d . . . H1 H -0.0756 0.9438 -0.0718 0.037 Uiso 1 1 d R . . C7 C 0.4934(4) 0.3648(4) 0.3369(2) 0.0290(8) Uani 1 1 d . . . H7 H 0.5151 0.4199 0.2936 0.035 Uiso 1 1 calc R . . C8 C 0.5963(4) 0.2955(4) 0.3824(2) 0.0263(8) Uani 1 1 d . . . H8 H 0.6857 0.3041 0.3704 0.032 Uiso 1 1 calc R . . C9 C 0.5686(4) 0.2120(4) 0.4466(2) 0.0235(7) Uani 1 1 d . . . C10 C 0.4355(4) 0.2040(4) 0.4594(2) 0.0244(7) Uani 1 1 d . . . H10 H 0.4120 0.1471 0.5014 0.029 Uiso 1 1 calc R . . C11 C 0.3379(4) 0.2779(4) 0.4115(2) 0.0259(8) Uani 1 1 d . . . H11 H 0.2475 0.2716 0.4222 0.031 Uiso 1 1 calc R . . C12 C 0.6771(4) 0.1416(4) 0.4958(2) 0.0241(7) Uani 1 1 d . . . H12 H 0.7665 0.1489 0.4800 0.029 Uiso 1 1 calc R . . C13 C 0.6617(4) 0.0684(4) 0.5605(2) 0.0247(7) Uani 1 1 d . . . H13 H 0.5711 0.0641 0.5763 0.030 Uiso 1 1 calc R . . C14 C 0.7686(4) -0.0060(4) 0.6101(2) 0.0229(7) Uani 1 1 d . . . C15 C 0.9059(4) -0.0053(4) 0.5960(2) 0.0244(7) Uani 1 1 d . . . H15 H 0.9310 0.0487 0.5531 0.029 Uiso 1 1 calc R . . C16 C 1.0046(4) -0.0811(4) 0.6430(2) 0.0245(7) Uani 1 1 d . . . H16 H 1.0967 -0.0790 0.6323 0.029 Uiso 1 1 calc R . . C17 C 0.9705(4) -0.1615(4) 0.7064(2) 0.0232(7) Uani 1 1 d . . . C18 C 0.8344(4) -0.1628(4) 0.7222(2) 0.0255(8) Uani 1 1 d . . . H18 H 0.8093 -0.2159 0.7654 0.031 Uiso 1 1 calc R . . C19 C 0.7368(4) -0.0861(4) 0.6744(2) 0.0260(8) Uani 1 1 d . . . H19 H 0.6444 -0.0877 0.6855 0.031 Uiso 1 1 calc R . . C20 C 1.0461(4) -0.3147(4) 0.8154(2) 0.0282(8) Uani 1 1 d . . . H20A H 1.0111 -0.3811 0.8070 0.034 Uiso 1 1 calc R . . H20B H 0.9726 -0.2561 0.8463 0.034 Uiso 1 1 calc R . . C21 C 1.1801(4) -0.3880(4) 0.8514(2) 0.0294(8) Uani 1 1 d . . . H21A H 1.2161 -0.3210 0.8581 0.035 Uiso 1 1 calc R . . H21B H 1.2525 -0.4474 0.8205 0.035 Uiso 1 1 calc R . . C22 C 1.1531(4) -0.4734(4) 0.9238(2) 0.0273(8) Uani 1 1 d . . . H22A H 1.0828 -0.4126 0.9547 0.033 Uiso 1 1 calc R . . H22B H 1.1122 -0.5364 0.9168 0.033 Uiso 1 1 calc R . . C23 C 1.2837(4) -0.5550(4) 0.9621(2) 0.0279(8) Uani 1 1 d . . . H23A H 1.3279 -0.4928 0.9670 0.034 Uiso 1 1 calc R . . H23B H 1.3521 -0.6199 0.9328 0.034 Uiso 1 1 calc R . . C24 C 1.2523(4) -0.6330(4) 1.0361(2) 0.0286(8) Uani 1 1 d . . . H24A H 1.1824 -0.5681 1.0650 0.034 Uiso 1 1 calc R . . H24B H 1.2098 -0.6963 1.0310 0.034 Uiso 1 1 calc R . . C25 C 1.3820(4) -0.7130(5) 1.0755(2) 0.0342(9) Uani 1 1 d . . . H25A H 1.4523 -0.7767 1.0470 0.051 Uiso 1 1 calc R . . H25B H 1.3558 -0.7634 1.1217 0.051 Uiso 1 1 calc R . . H25C H 1.4215 -0.6504 1.0834 0.051 Uiso 1 1 calc R . . N1 N 0.3641(4) 0.3591(3) 0.35011(19) 0.0293(7) Uani 1 1 d . . . O2 O 1.0770(3) -0.2336(3) 0.74856(15) 0.0278(6) Uani 1 1 d . . . C26 C 0.8040(4) 0.0752(4) 0.8221(2) 0.0269(8) Uani 1 1 d . . . H26 H 0.9001 0.0592 0.8051 0.032 Uiso 1 1 calc R . . C27 C 0.7050(4) 0.1544(4) 0.7762(2) 0.0243(7) Uani 1 1 d . . . H27 H 0.7331 0.1918 0.7288 0.029 Uiso 1 1 calc R . . C28 C 0.5616(4) 0.1806(4) 0.7991(2) 0.0233(7) Uani 1 1 d . . . C29 C 0.5301(4) 0.1205(4) 0.8696(2) 0.0302(9) Uani 1 1 d . . . H29 H 0.4351 0.1337 0.8880 0.036 Uiso 1 1 calc R . . C30 C 0.6365(4) 0.0422(4) 0.9125(2) 0.0316(9) Uani 1 1 d . . . H30 H 0.6120 0.0031 0.9602 0.038 Uiso 1 1 calc R . . C31 C 0.4484(4) 0.2653(4) 0.7546(2) 0.0251(8) Uani 1 1 d . . . H31 H 0.3551 0.2863 0.7777 0.030 Uiso 1 1 calc R . . C32 C 0.4622(4) 0.3168(4) 0.6846(2) 0.0234(7) Uani 1 1 d . . . H32 H 0.5554 0.2941 0.6612 0.028 Uiso 1 1 calc R . . C33 C 0.3487(4) 0.4043(4) 0.6407(2) 0.0220(7) Uani 1 1 d . . . C34 C 0.3777(4) 0.4323(4) 0.5662(2) 0.0222(7) Uani 1 1 d . . . H34 H 0.4718 0.3941 0.5454 0.027 Uiso 1 1 calc R . . C35 C 0.2738(4) 0.5141(4) 0.5217(2) 0.0222(7) Uani 1 1 d . . . H35 H 0.2962 0.5309 0.4713 0.027 Uiso 1 1 calc R . . C36 C 0.1354(4) 0.5714(4) 0.5524(2) 0.0225(7) Uani 1 1 d . . . C37 C 0.1049(4) 0.5473(4) 0.6264(2) 0.0240(7) Uani 1 1 d . . . H37 H 0.0114 0.5880 0.6473 0.029 Uiso 1 1 calc R . . C38 C 0.2085(4) 0.4653(4) 0.66928(19) 0.0227(7) Uani 1 1 d . . . H38 H 0.1853 0.4492 0.7196 0.027 Uiso 1 1 calc R . . C39 C 0.0426(4) 0.6759(4) 0.43782(19) 0.0239(7) Uani 1 1 d . . . H39A H 0.0745 0.5896 0.4206 0.029 Uiso 1 1 calc R . . H39B H 0.1135 0.7187 0.4190 0.029 Uiso 1 1 calc R . . C40 C -0.0997(4) 0.7697(4) 0.4141(2) 0.0253(8) Uani 1 1 d . . . H40A H -0.1353 0.8488 0.4379 0.030 Uiso 1 1 calc R . . H40B H -0.1662 0.7214 0.4299 0.030 Uiso 1 1 calc R . . C41 C -0.0969(4) 0.8199(4) 0.3340(2) 0.0255(8) Uani 1 1 d . . . H41A H -0.0677 0.7415 0.3102 0.031 Uiso 1 1 calc R . . H41B H -0.0262 0.8632 0.3176 0.031 Uiso 1 1 calc R . . C42 C -0.2401(4) 0.9217(4) 0.3119(2) 0.0244(7) Uani 1 1 d . . . H42A H -0.3062 0.8734 0.3204 0.029 Uiso 1 1 calc R . . H42B H -0.2774 0.9904 0.3429 0.029 Uiso 1 1 calc R . . C43 C -0.2364(4) 0.9938(4) 0.2346(2) 0.0298(8) Uani 1 1 d . . . H43A H -0.1957 0.9253 0.2035 0.036 Uiso 1 1 calc R . . H43B H -0.1739 1.0458 0.2264 0.036 Uiso 1 1 calc R . . C44 C -0.3814(4) 1.0902(5) 0.2132(2) 0.0336(9) Uani 1 1 d . . . H44A H -0.4425 1.0387 0.2188 0.050 Uiso 1 1 calc R . . H44B H -0.3724 1.1357 0.1632 0.050 Uiso 1 1 calc R . . H44C H -0.4225 1.1581 0.2439 0.050 Uiso 1 1 calc R . . N2 N 0.7728(3) 0.0187(3) 0.88995(18) 0.0272(7) Uani 1 1 d . . . O3 O 0.0231(3) 0.6522(3) 0.51496(14) 0.0280(6) 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 C1 0.0273(18) 0.0228(17) 0.0078(14) 0.0066(13) -0.0059(13) -0.0088(14) C2 0.0163(16) 0.029(2) 0.032(2) -0.0073(16) -0.0010(15) -0.0063(15) C3 0.0216(17) 0.034(2) 0.0179(17) 0.0020(15) 0.0028(14) -0.0129(16) C4 0.0234(17) 0.0249(18) 0.0213(17) -0.0018(14) -0.0012(14) -0.0097(15) C5 0.0174(16) 0.0261(19) 0.0256(18) -0.0066(15) -0.0007(14) -0.0056(14) C6 0.0178(16) 0.0283(19) 0.0218(17) -0.0086(15) 0.0092(13) -0.0113(14) F1 0.0169(10) 0.0508(16) 0.0350(13) 0.0041(12) -0.0034(9) -0.0118(10) F2 0.0230(12) 0.0645(18) 0.0312(13) 0.0074(12) 0.0037(10) -0.0202(12) F3 0.0158(10) 0.0421(14) 0.0309(12) -0.0025(11) -0.0001(9) -0.0073(10) F4 0.0219(11) 0.0391(13) 0.0258(12) -0.0001(10) 0.0055(9) -0.0136(10) I1 0.02455(13) 0.02509(13) 0.02245(13) -0.00170(9) -0.00117(9) -0.00878(9) O1 0.0238(13) 0.0397(17) 0.0238(14) 0.0018(12) -0.0027(11) -0.0096(12) C7 0.0286(19) 0.028(2) 0.0260(19) 0.0001(16) -0.0006(16) -0.0100(16) C8 0.0232(18) 0.0262(19) 0.030(2) -0.0060(16) 0.0031(15) -0.0113(15) C9 0.0231(17) 0.0208(17) 0.0252(18) -0.0052(15) -0.0004(14) -0.0071(14) C10 0.0249(18) 0.0264(19) 0.0196(17) -0.0017(15) 0.0007(14) -0.0100(15) C11 0.0244(18) 0.029(2) 0.0237(18) -0.0035(15) -0.0027(15) -0.0098(15) C12 0.0173(16) 0.0246(18) 0.0281(19) -0.0063(15) -0.0005(14) -0.0056(14) C13 0.0225(17) 0.0253(19) 0.0266(19) -0.0083(15) 0.0029(14) -0.0095(15) C14 0.0230(17) 0.0212(17) 0.0242(18) -0.0057(14) 0.0016(14) -0.0088(14) C15 0.0244(18) 0.0241(18) 0.0234(18) -0.0047(15) 0.0037(14) -0.0103(15) C16 0.0209(17) 0.0269(19) 0.0251(18) -0.0061(15) 0.0039(14) -0.0104(15) C17 0.0235(17) 0.0219(18) 0.0245(18) -0.0060(15) -0.0004(14) -0.0086(14) C18 0.0247(18) 0.0274(19) 0.0235(18) -0.0013(15) -0.0001(14) -0.0119(15) C19 0.0204(17) 0.030(2) 0.0274(19) -0.0056(16) 0.0026(15) -0.0119(15) C20 0.0277(19) 0.029(2) 0.0257(19) -0.0018(16) -0.0030(15) -0.0107(16) C21 0.0254(19) 0.030(2) 0.030(2) -0.0030(17) -0.0051(16) -0.0083(16) C22 0.0217(18) 0.0257(19) 0.033(2) -0.0063(16) -0.0046(15) -0.0062(15) C23 0.0197(17) 0.031(2) 0.029(2) -0.0064(16) -0.0010(15) -0.0056(15) C24 0.0219(18) 0.031(2) 0.0271(19) -0.0022(16) -0.0035(15) -0.0052(16) C25 0.027(2) 0.035(2) 0.032(2) 0.0014(18) -0.0072(17) -0.0048(17) N1 0.0277(17) 0.0274(17) 0.0341(18) -0.0046(14) -0.0108(14) -0.0087(14) O2 0.0254(13) 0.0321(15) 0.0232(13) 0.0023(11) -0.0023(11) -0.0124(12) C26 0.0208(17) 0.031(2) 0.0278(19) -0.0053(16) -0.0016(15) -0.0092(15) C27 0.0221(17) 0.030(2) 0.0190(17) 0.0007(15) -0.0016(14) -0.0110(15) C28 0.0233(17) 0.0212(17) 0.0244(18) -0.0026(14) -0.0017(14) -0.0085(14) C29 0.0215(18) 0.035(2) 0.028(2) -0.0015(17) 0.0017(15) -0.0091(16) C30 0.027(2) 0.037(2) 0.025(2) 0.0022(17) -0.0011(16) -0.0116(17) C31 0.0210(17) 0.0230(18) 0.0283(19) -0.0028(15) -0.0009(15) -0.0070(14) C32 0.0224(17) 0.0229(18) 0.0236(18) -0.0022(15) -0.0021(14) -0.0085(14) C33 0.0223(17) 0.0187(17) 0.0250(18) -0.0016(14) -0.0016(14) -0.0095(14) C34 0.0190(16) 0.0229(18) 0.0235(18) -0.0033(14) 0.0019(14) -0.0091(14) C35 0.0215(17) 0.0220(18) 0.0222(17) -0.0044(14) 0.0011(14) -0.0085(14) C36 0.0213(17) 0.0202(17) 0.0237(18) -0.0009(14) 0.0009(14) -0.0088(14) C37 0.0195(17) 0.0233(18) 0.0258(18) -0.0049(15) 0.0019(14) -0.0061(14) C38 0.0249(18) 0.0234(18) 0.0171(16) 0.0003(14) 0.0011(14) -0.0101(15) C39 0.0236(17) 0.0252(18) 0.0181(17) 0.0025(14) -0.0033(14) -0.0074(15) C40 0.0197(17) 0.0248(19) 0.0285(19) -0.0021(15) -0.0017(14) -0.0074(15) C41 0.0205(17) 0.0231(18) 0.030(2) -0.0061(15) -0.0014(15) -0.0044(14) C42 0.0222(17) 0.0240(18) 0.0253(18) -0.0018(15) -0.0011(14) -0.0090(15) C43 0.0239(18) 0.032(2) 0.026(2) -0.0007(16) -0.0020(15) -0.0064(16) C44 0.026(2) 0.041(2) 0.027(2) 0.0018(18) -0.0036(16) -0.0086(18) N2 0.0241(16) 0.0287(17) 0.0268(17) -0.0022(14) -0.0041(13) -0.0087(13) O3 0.0197(12) 0.0333(15) 0.0223(13) -0.0011(11) -0.0013(10) -0.0036(11) _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 C6 1.374(5) . ? C1 C2 1.386(5) . ? C1 I1 2.102(3) . ? C2 F1 1.345(4) . ? C2 C3 1.375(5) . ? C3 F2 1.340(4) . ? C3 C4 1.391(5) . ? C4 O1 1.317(5) . ? C4 C5 1.400(5) . ? C5 F3 1.351(4) . ? C5 C6 1.386(5) . ? C6 F4 1.351(4) . ? I1 N1 2.872(3) . ? O1 H1 0.9118 . ? C7 N1 1.344(5) . ? C7 C8 1.376(6) . ? C7 H7 0.9500 . ? C8 C9 1.405(5) . ? C8 H8 0.9500 . ? C9 C10 1.393(5) . ? C9 C12 1.464(5) . ? C10 C11 1.376(5) . ? C10 H10 0.9500 . ? C11 N1 1.350(5) . ? C11 H11 0.9500 . ? C12 C13 1.330(5) . ? C12 H12 0.9500 . ? C13 C14 1.461(5) . ? C13 H13 0.9500 . ? C14 C19 1.399(5) . ? C14 C15 1.405(5) . ? C15 C16 1.374(5) . ? C15 H15 0.9500 . ? C16 C17 1.397(5) . ? C16 H16 0.9500 . ? C17 O2 1.364(5) . ? C17 C18 1.395(5) . ? C18 C19 1.379(5) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 O2 1.437(5) . ? C20 C21 1.513(5) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C22 1.526(6) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C23 1.516(5) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.525(6) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C25 1.519(5) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 N2 1.346(5) . ? C26 C27 1.368(5) . ? C26 H26 0.9500 . ? C27 C28 1.405(5) . ? C27 H27 0.9500 . ? C28 C29 1.401(5) . ? C28 C31 1.457(5) . ? C29 C30 1.380(6) . ? C29 H29 0.9500 . ? C30 N2 1.340(5) . ? C30 H30 0.9500 . ? C31 C32 1.339(5) . ? C31 H31 0.9500 . ? C32 C33 1.459(5) . ? C32 H32 0.9500 . ? C33 C34 1.402(5) . ? C33 C38 1.406(5) . ? C34 C35 1.388(5) . ? C34 H34 0.9500 . ? C35 C36 1.400(5) . ? C35 H35 0.9500 . ? C36 O3 1.367(4) . ? C36 C37 1.391(5) . ? C37 C38 1.368(5) . ? C37 H37 0.9500 . ? C38 H38 0.9500 . ? C39 O3 1.443(4) . ? C39 C40 1.511(5) . ? C39 H39A 0.9900 . ? C39 H39B 0.9900 . ? C40 C41 1.514(5) . ? C40 H40A 0.9900 . ? C40 H40B 0.9900 . ? C41 C42 1.530(5) . ? C41 H41A 0.9900 . ? C41 H41B 0.9900 . ? C42 C43 1.514(5) . ? C42 H42A 0.9900 . ? C42 H42B 0.9900 . ? C43 C44 1.525(6) . ? C43 H43A 0.9900 . ? C43 H43B 0.9900 . ? C44 H44A 0.9800 . ? C44 H44B 0.9800 . ? C44 H44C 0.9800 . ? 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 C6 C1 C2 116.7(3) . . ? C6 C1 I1 123.0(3) . . ? C2 C1 I1 120.2(3) . . ? F1 C2 C3 118.6(3) . . ? F1 C2 C1 119.7(4) . . ? C3 C2 C1 121.8(3) . . ? F2 C3 C2 119.2(3) . . ? F2 C3 C4 118.4(3) . . ? C2 C3 C4 122.5(3) . . ? O1 C4 C3 119.1(3) . . ? O1 C4 C5 125.6(3) . . ? C3 C4 C5 115.3(3) . . ? F3 C5 C6 119.7(3) . . ? F3 C5 C4 118.4(3) . . ? C6 C5 C4 121.9(3) . . ? F4 C6 C1 120.8(3) . . ? F4 C6 C5 117.4(3) . . ? C1 C6 C5 121.9(3) . . ? C1 I1 N1 169.50(12) . . ? C4 O1 H1 123.2 . . ? N1 C7 C8 123.8(4) . . ? N1 C7 H7 118.1 . . ? C8 C7 H7 118.1 . . ? C7 C8 C9 119.7(4) . . ? C7 C8 H8 120.1 . . ? C9 C8 H8 120.1 . . ? C10 C9 C8 116.3(4) . . ? C10 C9 C12 124.3(3) . . ? C8 C9 C12 119.5(3) . . ? C11 C10 C9 120.4(4) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? N1 C11 C10 123.3(4) . . ? N1 C11 H11 118.3 . . ? C10 C11 H11 118.3 . . ? C13 C12 C9 125.9(4) . . ? C13 C12 H12 117.0 . . ? C9 C12 H12 117.0 . . ? C12 C13 C14 127.3(4) . . ? C12 C13 H13 116.3 . . ? C14 C13 H13 116.3 . . ? C19 C14 C15 117.0(4) . . ? C19 C14 C13 119.7(3) . . ? C15 C14 C13 123.3(3) . . ? C16 C15 C14 121.3(4) . . ? C16 C15 H15 119.4 . . ? C14 C15 H15 119.4 . . ? C15 C16 C17 120.6(3) . . ? C15 C16 H16 119.7 . . ? C17 C16 H16 119.7 . . ? O2 C17 C18 125.1(3) . . ? O2 C17 C16 115.5(3) . . ? C18 C17 C16 119.3(4) . . ? C19 C18 C17 119.3(4) . . ? C19 C18 H18 120.4 . . ? C17 C18 H18 120.4 . . ? C18 C19 C14 122.5(3) . . ? C18 C19 H19 118.7 . . ? C14 C19 H19 118.7 . . ? O2 C20 C21 108.2(3) . . ? O2 C20 H20A 110.1 . . ? C21 C20 H20A 110.1 . . ? O2 C20 H20B 110.1 . . ? C21 C20 H20B 110.1 . . ? H20A C20 H20B 108.4 . . ? C20 C21 C22 110.6(3) . . ? C20 C21 H21A 109.5 . . ? C22 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? C22 C21 H21B 109.5 . . ? H21A C21 H21B 108.1 . . ? C23 C22 C21 113.9(3) . . ? C23 C22 H22A 108.8 . . ? C21 C22 H22A 108.8 . . ? C23 C22 H22B 108.8 . . ? C21 C22 H22B 108.8 . . ? H22A C22 H22B 107.7 . . ? C22 C23 C24 112.8(3) . . ? C22 C23 H23A 109.0 . . ? C24 C23 H23A 109.0 . . ? C22 C23 H23B 109.0 . . ? C24 C23 H23B 109.0 . . ? H23A C23 H23B 107.8 . . ? C25 C24 C23 113.3(3) . . ? C25 C24 H24A 108.9 . . ? C23 C24 H24A 108.9 . . ? C25 C24 H24B 108.9 . . ? C23 C24 H24B 108.9 . . ? H24A C24 H24B 107.7 . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C7 N1 C11 116.5(3) . . ? C7 N1 I1 106.7(3) . . ? C11 N1 I1 136.8(3) . . ? C17 O2 C20 117.7(3) . . ? N2 C26 C27 123.6(4) . . ? N2 C26 H26 118.2 . . ? C27 C26 H26 118.2 . . ? C26 C27 C28 120.1(4) . . ? C26 C27 H27 120.0 . . ? C28 C27 H27 120.0 . . ? C29 C28 C27 115.9(3) . . ? C29 C28 C31 120.0(3) . . ? C27 C28 C31 124.1(3) . . ? C30 C29 C28 120.4(4) . . ? C30 C29 H29 119.8 . . ? C28 C29 H29 119.8 . . ? N2 C30 C29 123.0(4) . . ? N2 C30 H30 118.5 . . ? C29 C30 H30 118.5 . . ? C32 C31 C28 126.8(4) . . ? C32 C31 H31 116.6 . . ? C28 C31 H31 116.6 . . ? C31 C32 C33 126.6(4) . . ? C31 C32 H32 116.7 . . ? C33 C32 H32 116.7 . . ? C34 C33 C38 116.9(3) . . ? C34 C33 C32 119.7(3) . . ? C38 C33 C32 123.4(3) . . ? C35 C34 C33 122.3(3) . . ? C35 C34 H34 118.9 . . ? C33 C34 H34 118.9 . . ? C34 C35 C36 118.8(3) . . ? C34 C35 H35 120.6 . . ? C36 C35 H35 120.6 . . ? O3 C36 C37 115.3(3) . . ? O3 C36 C35 124.8(3) . . ? C37 C36 C35 119.8(3) . . ? C38 C37 C36 120.4(3) . . ? C38 C37 H37 119.8 . . ? C36 C37 H37 119.8 . . ? C37 C38 C33 121.7(3) . . ? C37 C38 H38 119.1 . . ? C33 C38 H38 119.1 . . ? O3 C39 C40 105.6(3) . . ? O3 C39 H39A 110.6 . . ? C40 C39 H39A 110.6 . . ? O3 C39 H39B 110.6 . . ? C40 C39 H39B 110.6 . . ? H39A C39 H39B 108.8 . . ? C39 C40 C41 113.5(3) . . ? C39 C40 H40A 108.9 . . ? C41 C40 H40A 108.9 . . ? C39 C40 H40B 108.9 . . ? C41 C40 H40B 108.9 . . ? H40A C40 H40B 107.7 . . ? C40 C41 C42 112.4(3) . . ? C40 C41 H41A 109.1 . . ? C42 C41 H41A 109.1 . . ? C40 C41 H41B 109.1 . . ? C42 C41 H41B 109.1 . . ? H41A C41 H41B 107.9 . . ? C43 C42 C41 114.1(3) . . ? C43 C42 H42A 108.7 . . ? C41 C42 H42A 108.7 . . ? C43 C42 H42B 108.7 . . ? C41 C42 H42B 108.7 . . ? H42A C42 H42B 107.6 . . ? C42 C43 C44 113.0(3) . . ? C42 C43 H43A 109.0 . . ? C44 C43 H43A 109.0 . . ? C42 C43 H43B 109.0 . . ? C44 C43 H43B 109.0 . . ? H43A C43 H43B 107.8 . . ? C43 C44 H44A 109.5 . . ? C43 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? C43 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? C30 N2 C26 117.0(3) . . ? C36 O3 C39 119.4(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 F1 -179.8(3) . . . . ? I1 C1 C2 F1 -1.2(5) . . . . ? C6 C1 C2 C3 0.5(6) . . . . ? I1 C1 C2 C3 179.2(3) . . . . ? F1 C2 C3 F2 -0.4(6) . . . . ? C1 C2 C3 F2 179.2(4) . . . . ? F1 C2 C3 C4 179.7(4) . . . . ? C1 C2 C3 C4 -0.7(6) . . . . ? F2 C3 C4 O1 1.1(6) . . . . ? C2 C3 C4 O1 -179.0(4) . . . . ? F2 C3 C4 C5 -178.7(4) . . . . ? C2 C3 C4 C5 1.1(6) . . . . ? O1 C4 C5 F3 -1.2(6) . . . . ? C3 C4 C5 F3 178.6(3) . . . . ? O1 C4 C5 C6 178.6(4) . . . . ? C3 C4 C5 C6 -1.5(6) . . . . ? C2 C1 C6 F4 179.8(3) . . . . ? I1 C1 C6 F4 1.2(5) . . . . ? C2 C1 C6 C5 -1.0(6) . . . . ? I1 C1 C6 C5 -179.5(3) . . . . ? F3 C5 C6 F4 0.6(5) . . . . ? C4 C5 C6 F4 -179.2(3) . . . . ? F3 C5 C6 C1 -178.6(3) . . . . ? C4 C5 C6 C1 1.6(6) . . . . ? C6 C1 I1 N1 -163.5(5) . . . . ? C2 C1 I1 N1 17.9(9) . . . . ? N1 C7 C8 C9 0.6(6) . . . . ? C7 C8 C9 C10 0.8(6) . . . . ? C7 C8 C9 C12 -178.2(4) . . . . ? C8 C9 C10 C11 -1.6(6) . . . . ? C12 C9 C10 C11 177.4(4) . . . . ? C9 C10 C11 N1 1.2(6) . . . . ? C10 C9 C12 C13 -4.6(6) . . . . ? C8 C9 C12 C13 174.4(4) . . . . ? C9 C12 C13 C14 178.2(4) . . . . ? C12 C13 C14 C19 -175.4(4) . . . . ? C12 C13 C14 C15 2.6(6) . . . . ? C19 C14 C15 C16 0.7(6) . . . . ? C13 C14 C15 C16 -177.4(4) . . . . ? C14 C15 C16 C17 0.0(6) . . . . ? C15 C16 C17 O2 179.3(3) . . . . ? C15 C16 C17 C18 -0.8(6) . . . . ? O2 C17 C18 C19 -179.2(4) . . . . ? C16 C17 C18 C19 0.9(6) . . . . ? C17 C18 C19 C14 -0.2(6) . . . . ? C15 C14 C19 C18 -0.6(6) . . . . ? C13 C14 C19 C18 177.5(4) . . . . ? O2 C20 C21 C22 178.6(3) . . . . ? C20 C21 C22 C23 177.6(3) . . . . ? C21 C22 C23 C24 176.8(3) . . . . ? C22 C23 C24 C25 -178.9(4) . . . . ? C8 C7 N1 C11 -1.1(6) . . . . ? C8 C7 N1 I1 -178.7(3) . . . . ? C10 C11 N1 C7 0.3(6) . . . . ? C10 C11 N1 I1 176.9(3) . . . . ? C1 I1 N1 C7 -4.5(8) . . . . ? C1 I1 N1 C11 178.6(6) . . . . ? C18 C17 O2 C20 -1.8(5) . . . . ? C16 C17 O2 C20 178.2(3) . . . . ? C21 C20 O2 C17 178.3(3) . . . . ? N2 C26 C27 C28 -0.1(6) . . . . ? C26 C27 C28 C29 -0.4(6) . . . . ? C26 C27 C28 C31 179.0(4) . . . . ? C27 C28 C29 C30 0.6(6) . . . . ? C31 C28 C29 C30 -178.8(4) . . . . ? C28 C29 C30 N2 -0.4(7) . . . . ? C29 C28 C31 C32 -172.0(4) . . . . ? C27 C28 C31 C32 8.6(6) . . . . ? C28 C31 C32 C33 -178.4(4) . . . . ? C31 C32 C33 C34 -169.8(4) . . . . ? C31 C32 C33 C38 11.1(6) . . . . ? C38 C33 C34 C35 -1.3(5) . . . . ? C32 C33 C34 C35 179.6(3) . . . . ? C33 C34 C35 C36 0.5(5) . . . . ? C34 C35 C36 O3 -179.2(3) . . . . ? C34 C35 C36 C37 0.9(5) . . . . ? O3 C36 C37 C38 178.5(3) . . . . ? C35 C36 C37 C38 -1.5(6) . . . . ? C36 C37 C38 C33 0.8(6) . . . . ? C34 C33 C38 C37 0.6(5) . . . . ? C32 C33 C38 C37 179.7(4) . . . . ? O3 C39 C40 C41 173.3(3) . . . . ? C39 C40 C41 C42 -176.3(3) . . . . ? C40 C41 C42 C43 169.3(3) . . . . ? C41 C42 C43 C44 177.6(4) . . . . ? C29 C30 N2 C26 -0.2(6) . . . . ? C27 C26 N2 C30 0.4(6) . . . . ? C37 C36 O3 C39 -176.1(3) . . . . ? C35 C36 O3 C39 4.0(5) . . . . ? C40 C39 O3 C36 -179.1(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 N2 0.91 1.69 2.586(4) 168.7 1_464 _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 1.836 _refine_diff_density_min -1.119 _refine_diff_density_rms 0.137 # Attachment 'Cif2.cif' data_dwb0814m _database_code_depnum_ccdc_archive 'CCDC 694376' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H13 N O, C6 H F4 I O' _chemical_formula_sum 'C20 H14 F4 I N O2' _chemical_formula_weight 503.22 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 6.0363(5) _cell_length_b 8.5988(6) _cell_length_c 35.409(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1837.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 6280 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 27.35 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.819 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 984 _exptl_absorpt_coefficient_mu 1.798 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.766 _exptl_absorpt_correction_T_max 0.931 _exptl_absorpt_process_details 'SADABS v2.03; (Sheldrick)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20820 _diffrn_reflns_av_R_equivalents 0.0358 _diffrn_reflns_av_sigmaI/netI 0.0370 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -49 _diffrn_reflns_limit_l_max 49 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 30.01 _reflns_number_total 5331 _reflns_number_gt 4841 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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. There is evidence of disorder of the stilbazole ring. This is in 2 forms which differ in the orientation of the double bond and also of the positioning of the two aromatic rings effectively by 180 degree rotation about the C17 N1 axis. The site of the alkene carbons are sufficiently different to allow discrimination and are two sites are modeled; the relative occupancy of whcih refined to 7:3. The two sites for each of the ring carbons (C7-C11, C14-C16, C18 & C19) were too close to be separated and therefore exhibit elliptical ADP which cover both sites. Attempts to model the two forms separately lead to NPD ADP's for those atoms. ; _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^)+(0.0453P)^2^+0.0300P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.01(2) _refine_ls_number_reflns 5331 _refine_ls_number_parameters 277 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0441 _refine_ls_R_factor_gt 0.0377 _refine_ls_wR_factor_ref 0.0865 _refine_ls_wR_factor_gt 0.0841 _refine_ls_goodness_of_fit_ref 1.134 _refine_ls_restrained_S_all 1.134 _refine_ls_shift/su_max 0.005 _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 C1 C 0.5717(5) 0.6524(4) 0.86003(9) 0.0182(6) Uani 1 1 d . . . C2 C 0.6409(5) 0.5453(3) 0.83311(9) 0.0169(6) Uani 1 1 d . . . C3 C 0.8421(5) 0.4717(3) 0.83937(9) 0.0150(6) Uani 1 1 d . . . C4 C 0.9687(5) 0.5047(4) 0.87064(8) 0.0183(5) Uani 1 1 d . . . C5 C 0.9019(6) 0.6129(4) 0.89768(9) 0.0190(6) Uani 1 1 d . . . C6 C 0.6982(6) 0.6836(3) 0.89158(9) 0.0179(6) Uani 1 1 d . . . F1 F 0.9185(3) 0.3671(2) 0.81429(5) 0.0215(4) Uani 1 1 d . . . F2 F 0.3775(4) 0.7259(2) 0.85628(6) 0.0258(4) Uani 1 1 d . . . F3 F 1.1609(3) 0.4288(2) 0.87603(6) 0.0221(4) Uani 1 1 d . . . F4 F 0.6243(4) 0.7878(2) 0.91737(6) 0.0252(5) Uani 1 1 d . . . I1 I 0.45669(3) 0.49828(3) 0.784971(5) 0.02357(7) Uani 1 1 d . . . O1 O 1.0319(5) 0.6381(3) 0.92767(7) 0.0248(5) Uani 1 1 d . . . H1 H 1.011(9) 0.717(6) 0.9390(13) 0.045(15) Uiso 1 1 d . . . C7 C 0.6050(7) 1.0806(4) 0.49600(11) 0.0272(8) Uani 1 1 d . . . H7 H 0.7443 1.1320 0.4958 0.033 Uiso 1 1 calc R . . C8 C 0.5579(8) 0.9783(5) 0.52549(10) 0.0365(10) Uani 1 1 d . A . H8 H 0.6639 0.9610 0.5449 0.044 Uiso 1 1 calc R . . C9 C 0.3553(8) 0.9017(4) 0.52640(10) 0.0333(9) Uani 1 1 d . . . C10 C 0.2124(7) 0.9310(4) 0.49693(11) 0.0305(9) Uani 1 1 d . A . H10 H 0.0730 0.8799 0.4959 0.037 Uiso 1 1 calc R . . C11 C 0.2705(6) 1.0335(4) 0.46907(10) 0.0242(8) Uani 1 1 d . . . H11 H 0.1673 1.0516 0.4493 0.029 Uiso 1 1 calc R A . C12A C 0.2664(9) 0.7913(5) 0.55514(15) 0.0157(14) Uani 0.696(13) 1 d P A 1 H12A H 0.1220 0.7491 0.5523 0.019 Uiso 0.696(13) 1 calc PR A 1 C13A C 0.3908(9) 0.7514(6) 0.58511(15) 0.0154(15) Uani 0.696(13) 1 d P A 1 H13A H 0.5378 0.7905 0.5862 0.019 Uiso 0.696(13) 1 calc PR A 1 C12B C 0.408(2) 0.8138(16) 0.5646(4) 0.028(4) Uani 0.304(13) 1 d P A 2 H12B H 0.5429 0.8250 0.5780 0.033 Uiso 0.304(13) 1 calc PR A 2 C13B C 0.247(2) 0.7249(16) 0.5756(4) 0.026(4) Uani 0.304(13) 1 d P A 2 H13B H 0.1136 0.7060 0.5622 0.031 Uiso 0.304(13) 1 calc PR A 2 C14 C 0.3145(9) 0.6510(4) 0.61648(11) 0.0391(11) Uani 1 1 d . . . C15 C 0.1131(9) 0.5767(5) 0.62099(10) 0.0383(11) Uani 1 1 d . A . H15 H 0.0053 0.5847 0.6015 0.046 Uiso 1 1 calc R . . C16 C 0.0626(6) 0.4888(4) 0.65380(9) 0.0244(6) Uani 1 1 d . . . H16 H -0.0763 0.4382 0.6565 0.029 Uiso 1 1 calc R A . C17 C 0.2223(6) 0.4795(4) 0.68159(9) 0.0194(7) Uani 1 1 d . A . C18 C 0.4256(7) 0.5535(4) 0.67688(12) 0.0317(9) Uani 1 1 d . . . H18 H 0.5352 0.5461 0.6961 0.038 Uiso 1 1 calc R A . C19 C 0.4684(8) 0.6367(5) 0.64477(12) 0.0397(10) Uani 1 1 d . A . H19 H 0.6084 0.6859 0.6420 0.048 Uiso 1 1 calc R . . C20 C 0.0004(7) 0.3144(4) 0.72043(10) 0.0280(8) Uani 1 1 d . A . H20A H -0.1271 0.3847 0.7192 0.042 Uiso 1 1 calc R . . H20B H 0.0047 0.2642 0.7453 0.042 Uiso 1 1 calc R . . H20C H -0.0129 0.2348 0.7007 0.042 Uiso 1 1 calc R . . N1 N 0.4625(5) 1.1096(3) 0.46796(8) 0.0220(6) Uani 1 1 d . A . O2 O 0.1996(4) 0.4010(3) 0.71477(7) 0.0247(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 C1 0.0121(15) 0.0183(14) 0.0242(16) 0.0022(12) 0.0012(12) 0.0014(11) C2 0.0136(14) 0.0176(14) 0.0196(15) 0.0023(10) 0.0008(12) -0.0037(11) C3 0.0159(14) 0.0115(16) 0.0177(13) -0.0015(10) 0.0060(11) -0.0023(10) C4 0.0148(12) 0.0173(12) 0.0230(13) 0.0009(16) 0.0002(10) -0.001(2) C5 0.0173(16) 0.0181(14) 0.0215(16) 0.0002(12) -0.0002(12) -0.0011(12) C6 0.0186(15) 0.0142(14) 0.0209(16) -0.0012(12) 0.0043(13) -0.0005(12) F1 0.0174(10) 0.0258(9) 0.0214(9) -0.0060(8) 0.0032(8) 0.0050(8) F2 0.0171(9) 0.0237(10) 0.0364(12) 0.0005(9) -0.0024(9) 0.0055(8) F3 0.0144(9) 0.0225(9) 0.0294(11) -0.0009(8) -0.0032(8) 0.0079(8) F4 0.0250(12) 0.0203(10) 0.0302(12) -0.0085(9) 0.0021(11) 0.0031(9) I1 0.01780(10) 0.02955(11) 0.02335(10) 0.00100(13) -0.00416(7) 0.00072(14) O1 0.0243(13) 0.0219(12) 0.0280(13) -0.0058(10) -0.0071(11) 0.0033(11) C7 0.0216(18) 0.0269(17) 0.033(2) -0.0073(15) -0.0040(15) -0.0010(14) C8 0.048(2) 0.037(2) 0.0246(17) -0.0060(16) -0.0140(15) 0.015(2) C9 0.057(3) 0.0215(17) 0.0212(18) -0.0021(14) 0.0168(18) 0.0076(19) C10 0.028(2) 0.0249(17) 0.038(2) -0.0059(16) 0.0110(18) -0.0060(16) C11 0.0197(16) 0.024(2) 0.0286(18) -0.0012(13) -0.0037(13) 0.0053(13) C12A 0.017(3) 0.014(2) 0.015(3) -0.0015(19) 0.0003(19) -0.0014(17) C13A 0.017(3) 0.014(2) 0.015(3) -0.002(2) 0.000(2) -0.0053(18) C12B 0.025(8) 0.037(7) 0.021(7) -0.002(6) 0.004(5) 0.003(5) C13B 0.031(8) 0.026(7) 0.020(7) -0.016(6) -0.002(5) -0.003(5) C14 0.075(3) 0.0197(17) 0.0229(19) 0.0035(15) 0.025(2) 0.0089(19) C15 0.069(3) 0.034(2) 0.0121(16) -0.0072(15) -0.0090(19) 0.021(2) C16 0.0285(16) 0.0213(15) 0.0234(14) -0.0028(15) -0.0024(12) 0.003(2) C17 0.0245(15) 0.0119(16) 0.0218(14) 0.0018(12) 0.0027(12) 0.0007(13) C18 0.029(2) 0.0243(16) 0.042(2) -0.0004(15) 0.0054(17) 0.0011(14) C19 0.048(2) 0.0269(18) 0.044(2) 0.0040(18) 0.023(2) 0.0003(19) C20 0.030(2) 0.0270(17) 0.0273(19) 0.0004(14) 0.0093(15) -0.0075(14) N1 0.0232(14) 0.0227(13) 0.0201(13) 0.0008(11) 0.0039(12) -0.0006(13) O2 0.0278(13) 0.0258(12) 0.0205(12) 0.0062(10) -0.0052(11) -0.0082(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 F2 1.338(4) . ? C1 C6 1.379(5) . ? C1 C2 1.390(4) . ? C2 C3 1.387(4) . ? C2 I1 2.075(3) . ? C3 F1 1.346(3) . ? C3 C4 1.375(4) . ? C4 F3 1.345(3) . ? C4 C5 1.395(4) . ? C5 O1 1.338(4) . ? C5 C6 1.389(5) . ? C6 F4 1.355(4) . ? O1 H1 0.80(5) . ? C7 N1 1.337(5) . ? C7 C8 1.395(6) . ? C7 H7 0.9500 . ? C8 C9 1.389(7) . ? C8 H8 0.9500 . ? C9 C10 1.377(6) . ? C9 C12A 1.491(6) . ? C9 C12B 1.580(15) . ? C10 C11 1.369(5) . ? C10 H10 0.9500 . ? C11 N1 1.331(5) . ? C11 H11 0.9500 . ? C12A C13A 1.344(8) . ? C12A H12A 0.9500 . ? C13A C14 1.481(6) . ? C13A H13A 0.9500 . ? C12B C13B 1.29(2) . ? C12B H12B 0.9500 . ? C13B C14 1.632(15) . ? C13B H13B 0.9500 . ? C14 C19 1.372(7) . ? C14 C15 1.383(7) . ? C15 C16 1.419(5) . ? C15 H15 0.9500 . ? C16 C17 1.380(4) . ? C16 H16 0.9500 . ? C17 O2 1.362(4) . ? C17 C18 1.392(5) . ? C18 C19 1.368(5) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 O2 1.428(4) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? 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 F2 C1 C6 118.3(3) . . ? F2 C1 C2 120.5(3) . . ? C6 C1 C2 121.2(3) . . ? C3 C2 C1 117.1(3) . . ? C3 C2 I1 120.8(2) . . ? C1 C2 I1 122.1(2) . . ? F1 C3 C4 118.6(3) . . ? F1 C3 C2 120.0(3) . . ? C4 C3 C2 121.4(3) . . ? F3 C4 C3 119.6(3) . . ? F3 C4 C5 118.4(3) . . ? C3 C4 C5 122.0(3) . . ? O1 C5 C6 124.9(3) . . ? O1 C5 C4 118.9(3) . . ? C6 C5 C4 116.2(3) . . ? F4 C6 C1 119.5(3) . . ? F4 C6 C5 118.4(3) . . ? C1 C6 C5 122.1(3) . . ? C5 O1 H1 116(4) . . ? N1 C7 C8 122.8(4) . . ? N1 C7 H7 118.6 . . ? C8 C7 H7 118.6 . . ? C9 C8 C7 119.7(4) . . ? C9 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? C10 C9 C8 116.5(3) . . ? C10 C9 C12A 114.1(4) . . ? C8 C9 C12A 129.4(4) . . ? C10 C9 C12B 149.4(7) . . ? C8 C9 C12B 94.0(7) . . ? C12A C9 C12B 35.3(5) . . ? C11 C10 C9 120.3(4) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? N1 C11 C10 124.1(3) . . ? N1 C11 H11 118.0 . . ? C10 C11 H11 118.0 . . ? C13A C12A C9 120.0(5) . . ? C13A C12A H12A 120.0 . . ? C9 C12A H12A 120.0 . . ? C12A C13A C14 124.6(5) . . ? C12A C13A H13A 117.7 . . ? C14 C13A H13A 117.7 . . ? C13B C12B C9 113.0(13) . . ? C13B C12B H12B 123.5 . . ? C9 C12B H12B 123.5 . . ? C12B C13B C14 108.2(12) . . ? C12B C13B H13B 125.9 . . ? C14 C13B H13B 125.9 . . ? C19 C14 C15 118.0(3) . . ? C19 C14 C13A 112.9(5) . . ? C15 C14 C13A 129.0(5) . . ? C19 C14 C13B 148.3(7) . . ? C15 C14 C13B 93.7(6) . . ? C13A C14 C13B 35.4(5) . . ? C14 C15 C16 122.0(4) . . ? C14 C15 H15 119.0 . . ? C16 C15 H15 119.0 . . ? C17 C16 C15 117.7(4) . . ? C17 C16 H16 121.2 . . ? C15 C16 H16 121.2 . . ? O2 C17 C16 125.0(3) . . ? O2 C17 C18 114.7(3) . . ? C16 C17 C18 120.3(3) . . ? C19 C18 C17 120.3(4) . . ? C19 C18 H18 119.8 . . ? C17 C18 H18 119.8 . . ? C18 C19 C14 121.7(4) . . ? C18 C19 H19 119.1 . . ? C14 C19 H19 119.1 . . ? O2 C20 H20A 109.5 . . ? O2 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O2 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C11 N1 C7 116.5(3) . . ? C17 O2 C20 117.7(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag F2 C1 C2 C3 -178.8(3) . . . . ? C6 C1 C2 C3 -0.1(5) . . . . ? F2 C1 C2 I1 2.2(4) . . . . ? C6 C1 C2 I1 -179.1(2) . . . . ? C1 C2 C3 F1 -179.9(3) . . . . ? I1 C2 C3 F1 -0.9(4) . . . . ? C1 C2 C3 C4 -0.7(4) . . . . ? I1 C2 C3 C4 178.3(2) . . . . ? F1 C3 C4 F3 -2.0(4) . . . . ? C2 C3 C4 F3 178.8(3) . . . . ? F1 C3 C4 C5 179.3(3) . . . . ? C2 C3 C4 C5 0.2(5) . . . . ? F3 C4 C5 O1 0.6(5) . . . . ? C3 C4 C5 O1 179.2(3) . . . . ? F3 C4 C5 C6 -177.5(3) . . . . ? C3 C4 C5 C6 1.1(5) . . . . ? F2 C1 C6 F4 -0.7(5) . . . . ? C2 C1 C6 F4 -179.4(3) . . . . ? F2 C1 C6 C5 -179.8(3) . . . . ? C2 C1 C6 C5 1.4(5) . . . . ? O1 C5 C6 F4 1.0(5) . . . . ? C4 C5 C6 F4 179.0(3) . . . . ? O1 C5 C6 C1 -179.9(3) . . . . ? C4 C5 C6 C1 -1.9(5) . . . . ? N1 C7 C8 C9 0.0(6) . . . . ? C7 C8 C9 C10 1.1(5) . . . . ? C7 C8 C9 C12A -178.4(4) . . . . ? C7 C8 C9 C12B -179.2(5) . . . . ? C8 C9 C10 C11 -1.4(5) . . . . ? C12A C9 C10 C11 178.2(3) . . . . ? C12B C9 C10 C11 179.4(10) . . . . ? C9 C10 C11 N1 0.5(6) . . . . ? C10 C9 C12A C13A 179.2(4) . . . . ? C8 C9 C12A C13A -1.3(7) . . . . ? C12B C9 C12A C13A 0.2(8) . . . . ? C9 C12A C13A C14 176.0(4) . . . . ? C10 C9 C12B C13B -0.9(17) . . . . ? C8 C9 C12B C13B 179.8(9) . . . . ? C12A C9 C12B C13B 0.9(7) . . . . ? C9 C12B C13B C14 -176.1(7) . . . . ? C12A C13A C14 C19 -175.9(4) . . . . ? C12A C13A C14 C15 2.1(7) . . . . ? C12A C13A C14 C13B 4.0(8) . . . . ? C12B C13B C14 C19 -2.4(16) . . . . ? C12B C13B C14 C15 176.0(9) . . . . ? C12B C13B C14 C13A -2.5(7) . . . . ? C19 C14 C15 C16 0.6(6) . . . . ? C13A C14 C15 C16 -177.3(4) . . . . ? C13B C14 C15 C16 -178.5(5) . . . . ? C14 C15 C16 C17 0.1(5) . . . . ? C15 C16 C17 O2 179.6(3) . . . . ? C15 C16 C17 C18 -0.6(5) . . . . ? O2 C17 C18 C19 -179.7(3) . . . . ? C16 C17 C18 C19 0.3(6) . . . . ? C17 C18 C19 C14 0.3(6) . . . . ? C15 C14 C19 C18 -0.8(6) . . . . ? C13A C14 C19 C18 177.4(4) . . . . ? C13B C14 C19 C18 177.4(9) . . . . ? C10 C11 N1 C7 0.6(5) . . . . ? C8 C7 N1 C11 -0.8(5) . . . . ? C16 C17 O2 C20 3.7(5) . . . . ? C18 C17 O2 C20 -176.2(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 N1 0.80(5) 1.82(5) 2.597(4) 165(6) 2_675 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 30.01 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.046 _refine_diff_density_min -1.103 _refine_diff_density_rms 0.100 # Attachment 'Cif3.cif' data_s93 _database_code_depnum_ccdc_archive 'CCDC 694377' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Prof. D. Bruce ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C31 H36 F5 N O2' _chemical_formula_weight 549.61 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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 6.0419(4) _cell_length_b 14.9401(11) _cell_length_c 16.9981(13) _cell_angle_alpha 109.712(4) _cell_angle_beta 99.798(3) _cell_angle_gamma 101.546(4) _cell_volume 1367.42(17) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 5660 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _exptl_crystal_description Block _exptl_crystal_colour 'Light Yellow' _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.335 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 580 _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9761 _exptl_absorpt_correction_T_max 0.9916 _exptl_absorpt_process_details 'SORTAV Blessing (1997)' _exptl_special_details ; PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD Area Detector' _diffrn_measurement_method '\f and \w scans to fill Ewald Sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22968 _diffrn_reflns_av_R_equivalents 0.1539 _diffrn_reflns_av_sigmaI/netI 0.1975 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _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 2.63 _diffrn_reflns_theta_max 27.55 _reflns_number_total 6154 _reflns_number_gt 2363 _reflns_threshold_expression >2sigma(I) _computing_data_collection ' DENZO (Otwinowski and Minor, 1997)' _computing_cell_refinement ' DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)' _computing_data_reduction ' DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997a)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997b)' _computing_molecular_graphics 'PLATON (Spek, 1990)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0485P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6154 _refine_ls_number_parameters 496 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2173 _refine_ls_R_factor_gt 0.0610 _refine_ls_wR_factor_ref 0.1406 _refine_ls_wR_factor_gt 0.1034 _refine_ls_goodness_of_fit_ref 0.913 _refine_ls_restrained_S_all 0.913 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F1 F 0.4733(3) 0.69450(12) 0.32785(10) 0.0438(5) Uani 1 1 d . . . F2 F 0.7157(3) 0.83800(12) 0.48284(10) 0.0492(5) Uani 1 1 d . . . F4 F 1.3691(3) 0.89808(12) 0.37212(10) 0.0466(5) Uani 1 1 d . . . F3 F 1.1656(3) 0.93991(12) 0.50754(10) 0.0480(5) Uani 1 1 d . . . F5 F 1.1296(3) 0.75591(12) 0.21759(10) 0.0446(5) Uani 1 1 d . . . O1 O 0.6866(4) 0.65050(15) 0.18930(12) 0.0406(6) Uani 1 1 d . . . O2 O -1.3018(3) -0.05858(14) -0.24075(12) 0.0405(6) Uani 1 1 d . . . N1 N 0.2675(4) 0.52846(16) 0.13808(15) 0.0375(7) Uani 1 1 d . . . C1 C 0.6968(5) 0.7448(2) 0.33796(18) 0.0322(8) Uani 1 1 d . . . C2 C 0.8192(5) 0.8181(2) 0.41685(18) 0.0363(8) Uani 1 1 d . . . C3 C 1.0445(5) 0.8695(2) 0.42967(18) 0.0363(8) Uani 1 1 d . . . C4 C 1.1465(5) 0.8474(2) 0.36177(19) 0.0362(8) Uani 1 1 d . . . C5 C 1.0234(5) 0.7741(2) 0.28295(18) 0.0341(8) Uani 1 1 d . . . C6 C 0.7954(5) 0.7208(2) 0.26828(18) 0.0319(7) Uani 1 1 d . . . C7 C 0.0839(5) 0.5202(2) 0.1722(2) 0.0381(8) Uani 1 1 d . . . C8 C -0.1240(6) 0.4474(2) 0.12965(19) 0.0353(8) Uani 1 1 d . . . C9 C -0.1522(5) 0.3768(2) 0.04762(17) 0.0318(8) Uani 1 1 d . . . C10 C 0.0387(5) 0.3855(2) 0.0120(2) 0.0359(8) Uani 1 1 d . . . C11 C 0.2422(6) 0.4610(2) 0.05833(19) 0.0348(8) Uani 1 1 d . . . C12 C -0.3754(5) 0.2997(2) 0.0046(2) 0.0348(8) Uani 1 1 d . . . C13 C -0.4345(5) 0.2306(2) -0.0755(2) 0.0362(8) Uani 1 1 d . . . C14 C -0.6579(5) 0.1540(2) -0.11806(17) 0.0315(7) Uani 1 1 d . . . C15 C -0.8301(5) 0.1385(2) -0.0752(2) 0.0360(8) Uani 1 1 d . . . C16 C -1.0427(5) 0.0678(2) -0.11758(19) 0.0378(8) Uani 1 1 d . . . C17 C -1.0855(5) 0.0094(2) -0.20563(18) 0.0348(8) Uani 1 1 d . . . C18 C -0.9172(5) 0.0225(2) -0.2489(2) 0.0339(8) Uani 1 1 d . . . C19 C -0.7048(5) 0.0938(2) -0.20534(18) 0.0344(8) Uani 1 1 d . . . C20 C -1.3630(6) -0.1207(2) -0.33106(19) 0.0349(8) Uani 1 1 d . . . C21 C -1.6060(6) -0.1868(3) -0.3521(2) 0.0389(8) Uani 1 1 d . . . C22 C -1.6922(6) -0.2616(2) -0.4449(2) 0.0382(8) Uani 1 1 d . . . C23 C -1.9422(6) -0.3240(2) -0.4652(2) 0.0373(8) Uani 1 1 d . . . C24 C -2.0356(6) -0.4008(2) -0.5571(2) 0.0362(8) Uani 1 1 d . . . C25 C -2.2887(6) -0.4589(2) -0.5770(2) 0.0382(8) Uani 1 1 d . . . C26 C -2.3883(6) -0.5354(2) -0.6694(2) 0.0373(8) Uani 1 1 d . . . C27 C -2.6362(5) -0.5977(2) -0.6868(2) 0.0363(8) Uani 1 1 d . . . C28 C -2.7331(6) -0.6793(2) -0.77625(19) 0.0341(8) Uani 1 1 d . . . C29 C -2.9777(6) -0.7423(2) -0.7901(2) 0.0351(8) Uani 1 1 d . . . C30 C -3.0749(6) -0.8252(2) -0.8791(2) 0.0392(8) Uani 1 1 d . . . C31 C -3.3236(7) -0.8851(3) -0.8938(3) 0.0515(10) Uani 1 1 d . . . H1 H 0.530(6) 0.615(2) 0.1817(19) 0.052(10) Uiso 1 1 d . . . H7 H 0.111(4) 0.5672(19) 0.2275(17) 0.027(7) Uiso 1 1 d . . . H8 H -0.250(4) 0.4472(17) 0.1605(15) 0.027(7) Uiso 1 1 d . . . H10 H 0.031(5) 0.339(2) -0.0458(19) 0.043(8) Uiso 1 1 d . . . H11 H 0.381(5) 0.471(2) 0.0362(16) 0.039(8) Uiso 1 1 d . . . H12 H -0.491(5) 0.3047(18) 0.0416(16) 0.034(8) Uiso 1 1 d . . . H13 H -0.327(4) 0.2322(16) -0.1104(14) 0.016(7) Uiso 1 1 d . . . H15 H -0.803(5) 0.178(2) -0.0129(18) 0.042(8) Uiso 1 1 d . . . H16 H -1.160(5) 0.058(2) -0.0844(17) 0.045(9) Uiso 1 1 d . . . H18 H -0.945(5) -0.017(2) -0.3071(19) 0.046(9) Uiso 1 1 d . . . H19 H -0.577(5) 0.1046(18) -0.2378(15) 0.032(7) Uiso 1 1 d . . . H20A H -1.236(6) -0.157(2) -0.340(2) 0.069(11) Uiso 1 1 d . . . H20B H -1.363(5) -0.079(2) -0.3657(18) 0.044(9) Uiso 1 1 d . . . H21A H -1.615(5) -0.216(2) -0.3117(17) 0.029(8) Uiso 1 1 d . . . H21B H -1.710(5) -0.146(2) -0.3381(18) 0.044(9) Uiso 1 1 d . . . H22A H -1.588(5) -0.304(2) -0.4529(17) 0.042(9) Uiso 1 1 d . . . H22B H -1.688(5) -0.228(2) -0.4873(18) 0.037(8) Uiso 1 1 d . . . H23A H -1.949(4) -0.3571(18) -0.4266(16) 0.020(7) Uiso 1 1 d . . . H23B H -2.048(5) -0.280(2) -0.4548(17) 0.043(9) Uiso 1 1 d . . . H24A H -1.938(5) -0.4468(19) -0.5660(15) 0.029(8) Uiso 1 1 d . . . H24B H -2.024(4) -0.3683(18) -0.5980(16) 0.026(8) Uiso 1 1 d . . . H25A H -2.312(5) -0.4948(19) -0.5382(17) 0.031(8) Uiso 1 1 d . . . H25B H -2.388(5) -0.412(2) -0.5665(16) 0.039(8) Uiso 1 1 d . . . H26A H -2.280(5) -0.5774(19) -0.6801(16) 0.032(8) Uiso 1 1 d . . . H26B H -2.387(5) -0.501(2) -0.7083(18) 0.037(9) Uiso 1 1 d . . . H27A H -2.649(4) -0.6271(19) -0.6423(17) 0.031(8) Uiso 1 1 d . . . H27B H -2.742(5) -0.5528(19) -0.6757(16) 0.035(8) Uiso 1 1 d . . . H28A H -2.619(4) -0.7229(19) -0.7864(15) 0.027(7) Uiso 1 1 d . . . H28B H -2.728(4) -0.6521(19) -0.8201(17) 0.030(8) Uiso 1 1 d . . . H29A H -2.984(4) -0.7692(18) -0.7456(16) 0.020(7) Uiso 1 1 d . . . H29B H -3.093(5) -0.699(2) -0.7801(16) 0.038(8) Uiso 1 1 d . . . H30A H -2.973(6) -0.869(2) -0.889(2) 0.059(11) Uiso 1 1 d . . . H30B H -3.070(5) -0.797(2) -0.9246(18) 0.040(9) Uiso 1 1 d . . . H31A H -3.332(5) -0.917(2) -0.8543(18) 0.034(9) Uiso 1 1 d . . . H31B H -3.435(6) -0.839(3) -0.885(2) 0.075(12) Uiso 1 1 d . . . H31C H -3.377(6) -0.937(3) -0.955(2) 0.070(11) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.0312(10) 0.0423(10) 0.0452(11) 0.0071(8) 0.0102(8) -0.0005(8) F2 0.0474(11) 0.0517(11) 0.0363(10) 0.0052(9) 0.0138(9) 0.0059(9) F4 0.0333(11) 0.0392(10) 0.0514(12) 0.0081(9) 0.0060(9) -0.0037(8) F3 0.0439(11) 0.0383(11) 0.0397(11) -0.0003(9) -0.0014(9) 0.0012(9) F5 0.0422(11) 0.0424(11) 0.0390(10) 0.0080(8) 0.0144(9) 0.0002(8) O1 0.0331(13) 0.0381(13) 0.0322(13) 0.0014(11) 0.0029(11) -0.0037(11) O2 0.0301(12) 0.0363(12) 0.0330(12) -0.0020(10) 0.0018(10) -0.0057(10) N1 0.0346(15) 0.0293(15) 0.0373(16) 0.0072(13) 0.0032(13) -0.0001(12) C1 0.0220(17) 0.0310(17) 0.0354(18) 0.0063(15) 0.0063(15) 0.0019(14) C2 0.042(2) 0.0369(19) 0.0297(18) 0.0102(16) 0.0131(16) 0.0104(16) C3 0.037(2) 0.0275(17) 0.0308(19) 0.0039(15) 0.0000(16) 0.0004(15) C4 0.0273(19) 0.0314(18) 0.042(2) 0.0106(16) 0.0057(16) 0.0001(15) C5 0.0365(19) 0.0309(18) 0.0329(18) 0.0098(15) 0.0107(16) 0.0077(15) C6 0.0285(18) 0.0267(17) 0.0348(19) 0.0096(15) 0.0027(15) 0.0042(15) C7 0.037(2) 0.0313(19) 0.0331(19) 0.0038(16) 0.0024(17) 0.0030(16) C8 0.036(2) 0.0309(18) 0.0336(19) 0.0075(15) 0.0085(16) 0.0066(16) C9 0.0317(18) 0.0238(17) 0.0332(18) 0.0081(14) 0.0027(15) 0.0030(14) C10 0.037(2) 0.0307(18) 0.0316(19) 0.0073(16) 0.0043(16) 0.0040(16) C11 0.034(2) 0.0323(18) 0.0351(19) 0.0140(16) 0.0066(16) 0.0028(16) C12 0.0311(18) 0.0317(18) 0.039(2) 0.0108(16) 0.0116(16) 0.0067(15) C13 0.0330(19) 0.0356(19) 0.038(2) 0.0123(17) 0.0112(17) 0.0071(16) C14 0.0301(18) 0.0261(17) 0.0321(18) 0.0088(15) 0.0028(15) 0.0031(14) C15 0.0349(19) 0.0288(17) 0.0326(18) 0.0038(15) 0.0053(16) 0.0012(15) C16 0.039(2) 0.0340(19) 0.0320(19) 0.0061(15) 0.0085(16) 0.0033(16) C17 0.0336(19) 0.0259(17) 0.0333(18) 0.0031(15) 0.0025(15) 0.0032(15) C18 0.0350(19) 0.0303(18) 0.0283(18) 0.0053(15) 0.0054(16) 0.0042(15) C19 0.0352(19) 0.0312(18) 0.0318(18) 0.0105(15) 0.0084(16) 0.0015(15) C20 0.033(2) 0.0318(19) 0.0281(18) 0.0039(16) 0.0020(15) 0.0019(16) C21 0.037(2) 0.0338(19) 0.034(2) 0.0051(17) 0.0054(16) 0.0028(16) C22 0.038(2) 0.0337(19) 0.0311(19) 0.0046(16) 0.0051(16) 0.0028(17) C23 0.038(2) 0.0305(19) 0.034(2) 0.0075(17) 0.0039(16) 0.0026(16) C24 0.034(2) 0.0288(19) 0.0332(19) 0.0034(16) 0.0034(16) 0.0012(16) C25 0.037(2) 0.0315(19) 0.0346(19) 0.0053(16) 0.0056(16) 0.0001(16) C26 0.033(2) 0.0334(19) 0.035(2) 0.0071(17) 0.0029(16) 0.0014(16) C27 0.0315(19) 0.0322(19) 0.0302(18) 0.0033(16) 0.0022(15) -0.0033(16) C28 0.036(2) 0.0337(19) 0.0248(18) 0.0064(15) 0.0065(15) 0.0040(15) C29 0.038(2) 0.0282(18) 0.0303(19) 0.0062(15) 0.0071(16) 0.0005(16) C30 0.040(2) 0.0324(19) 0.0331(19) 0.0059(16) 0.0034(16) 0.0017(17) C31 0.051(3) 0.044(2) 0.040(2) 0.007(2) 0.0036(19) -0.006(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C1 1.358(3) . ? F2 C2 1.351(3) . ? F4 C4 1.354(3) . ? F3 C3 1.348(3) . ? F5 C5 1.352(3) . ? O1 C6 1.345(3) . ? O1 H1 0.95(3) . ? O2 C17 1.375(3) . ? O2 C20 1.436(3) . ? N1 C7 1.340(4) . ? N1 C11 1.350(3) . ? C1 C2 1.375(4) . ? C1 C6 1.388(4) . ? C2 C3 1.363(4) . ? C3 C4 1.374(4) . ? C4 C5 1.376(4) . ? C5 C6 1.380(4) . ? C7 C8 1.378(4) . ? C7 H7 0.93(2) . ? C8 C9 1.393(4) . ? C8 H8 0.99(2) . ? C9 C10 1.394(4) . ? C9 C12 1.467(4) . ? C10 C11 1.386(4) . ? C10 H10 0.98(3) . ? C11 H11 0.98(3) . ? C12 C13 1.336(4) . ? C12 H12 1.02(3) . ? C13 C14 1.465(4) . ? C13 H13 0.95(2) . ? C14 C15 1.393(4) . ? C14 C19 1.395(4) . ? C15 C16 1.383(4) . ? C15 H15 0.99(3) . ? C16 C17 1.402(4) . ? C16 H16 0.99(3) . ? C17 C18 1.373(4) . ? C18 C19 1.388(4) . ? C18 H18 0.93(3) . ? C19 H19 1.04(3) . ? C20 C21 1.504(4) . ? C20 H20A 1.03(3) . ? C20 H20B 0.99(3) . ? C21 C22 1.518(4) . ? C21 H21A 0.94(3) . ? C21 H21B 0.97(3) . ? C22 C23 1.521(4) . ? C22 H22A 0.97(3) . ? C22 H22B 1.01(3) . ? C23 C24 1.519(4) . ? C23 H23A 0.95(3) . ? C23 H23B 1.00(3) . ? C24 C25 1.517(4) . ? C24 H24A 0.98(3) . ? C24 H24B 0.98(3) . ? C25 C26 1.526(4) . ? C25 H25A 0.99(3) . ? C25 H25B 1.00(3) . ? C26 C27 1.518(4) . ? C26 H26A 0.99(3) . ? C26 H26B 0.96(3) . ? C27 C28 1.517(4) . ? C27 H27A 1.00(3) . ? C27 H27B 1.01(3) . ? C28 C29 1.517(4) . ? C28 H28A 1.03(3) . ? C28 H28B 0.96(3) . ? C29 C30 1.520(4) . ? C29 H29A 0.97(3) . ? C29 H29B 1.04(3) . ? C30 C31 1.518(5) . ? C30 H30A 0.98(3) . ? C30 H30B 1.00(3) . ? C31 H31A 0.95(3) . ? C31 H31B 1.05(4) . ? C31 H31C 1.01(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 C6 O1 H1 116.3(18) . . ? C17 O2 C20 118.2(2) . . ? C7 N1 C11 117.0(3) . . ? F1 C1 C2 119.2(2) . . ? F1 C1 C6 119.0(2) . . ? C2 C1 C6 121.8(3) . . ? F2 C2 C3 119.7(2) . . ? F2 C2 C1 119.4(3) . . ? C3 C2 C1 120.9(3) . . ? F3 C3 C2 120.8(3) . . ? F3 C3 C4 120.6(3) . . ? C2 C3 C4 118.6(3) . . ? F4 C4 C3 120.0(3) . . ? F4 C4 C5 119.7(2) . . ? C3 C4 C5 120.3(3) . . ? F5 C5 C4 118.3(3) . . ? F5 C5 C6 119.5(2) . . ? C4 C5 C6 122.3(3) . . ? O1 C6 C5 118.7(3) . . ? O1 C6 C1 125.2(3) . . ? C5 C6 C1 116.2(3) . . ? N1 C7 C8 123.0(3) . . ? N1 C7 H7 113.9(16) . . ? C8 C7 H7 123.1(16) . . ? C7 C8 C9 120.7(3) . . ? C7 C8 H8 117.0(14) . . ? C9 C8 H8 122.2(14) . . ? C8 C9 C10 116.3(3) . . ? C8 C9 C12 119.2(3) . . ? C10 C9 C12 124.6(3) . . ? C11 C10 C9 120.0(3) . . ? C11 C10 H10 119.0(16) . . ? C9 C10 H10 121.0(16) . . ? N1 C11 C10 123.1(3) . . ? N1 C11 H11 113.6(15) . . ? C10 C11 H11 123.3(15) . . ? C13 C12 C9 126.4(3) . . ? C13 C12 H12 120.7(14) . . ? C9 C12 H12 112.8(14) . . ? C12 C13 C14 126.1(3) . . ? C12 C13 H13 118.3(14) . . ? C14 C13 H13 115.5(13) . . ? C15 C14 C19 117.6(3) . . ? C15 C14 C13 122.8(3) . . ? C19 C14 C13 119.6(3) . . ? C16 C15 C14 121.7(3) . . ? C16 C15 H15 117.6(16) . . ? C14 C15 H15 120.7(16) . . ? C15 C16 C17 119.3(3) . . ? C15 C16 H16 119.2(15) . . ? C17 C16 H16 121.5(16) . . ? C18 C17 O2 125.8(3) . . ? C18 C17 C16 120.0(3) . . ? O2 C17 C16 114.2(3) . . ? C17 C18 C19 119.9(3) . . ? C17 C18 H18 120.0(18) . . ? C19 C18 H18 120.0(18) . . ? C18 C19 C14 121.4(3) . . ? C18 C19 H19 120.4(13) . . ? C14 C19 H19 118.2(13) . . ? O2 C20 C21 107.0(2) . . ? O2 C20 H20A 106.6(18) . . ? C21 C20 H20A 114.9(19) . . ? O2 C20 H20B 109.4(16) . . ? C21 C20 H20B 109.3(17) . . ? H20A C20 H20B 109(3) . . ? C20 C21 C22 113.6(3) . . ? C20 C21 H21A 109.7(17) . . ? C22 C21 H21A 112.7(16) . . ? C20 C21 H21B 108.4(18) . . ? C22 C21 H21B 111.7(17) . . ? H21A C21 H21B 100(2) . . ? C21 C22 C23 112.3(3) . . ? C21 C22 H22A 107.3(17) . . ? C23 C22 H22A 109.9(18) . . ? C21 C22 H22B 111.4(15) . . ? C23 C22 H22B 107.3(16) . . ? H22A C22 H22B 109(2) . . ? C24 C23 C22 114.3(3) . . ? C24 C23 H23A 108.4(15) . . ? C22 C23 H23A 108.3(15) . . ? C24 C23 H23B 108.5(16) . . ? C22 C23 H23B 109.4(16) . . ? H23A C23 H23B 108(2) . . ? C25 C24 C23 113.3(3) . . ? C25 C24 H24A 109.2(15) . . ? C23 C24 H24A 108.5(15) . . ? C25 C24 H24B 107.8(15) . . ? C23 C24 H24B 109.6(15) . . ? H24A C24 H24B 108(2) . . ? C24 C25 C26 114.4(3) . . ? C24 C25 H25A 111.9(16) . . ? C26 C25 H25A 106.7(15) . . ? C24 C25 H25B 109.7(16) . . ? C26 C25 H25B 108.1(16) . . ? H25A C25 H25B 106(2) . . ? C27 C26 C25 113.8(3) . . ? C27 C26 H26A 111.0(16) . . ? C25 C26 H26A 106.8(15) . . ? C27 C26 H26B 108.5(17) . . ? C25 C26 H26B 108.3(16) . . ? H26A C26 H26B 108(2) . . ? C28 C27 C26 114.9(3) . . ? C28 C27 H27A 109.2(15) . . ? C26 C27 H27A 110.7(15) . . ? C28 C27 H27B 110.3(15) . . ? C26 C27 H27B 109.1(15) . . ? H27A C27 H27B 102(2) . . ? C29 C28 C27 113.4(3) . . ? C29 C28 H28A 110.5(15) . . ? C27 C28 H28A 108.6(14) . . ? C29 C28 H28B 110.7(16) . . ? C27 C28 H28B 110.4(15) . . ? H28A C28 H28B 103(2) . . ? C28 C29 C30 113.8(3) . . ? C28 C29 H29A 111.0(15) . . ? C30 C29 H29A 110.0(14) . . ? C28 C29 H29B 110.7(15) . . ? C30 C29 H29B 108.8(15) . . ? H29A C29 H29B 102(2) . . ? C31 C30 C29 113.4(3) . . ? C31 C30 H30A 110(2) . . ? C29 C30 H30A 110.3(19) . . ? C31 C30 H30B 108.8(17) . . ? C29 C30 H30B 109.7(16) . . ? H30A C30 H30B 104(3) . . ? C30 C31 H31A 110.9(18) . . ? C30 C31 H31B 110(2) . . ? H31A C31 H31B 108(3) . . ? C30 C31 H31C 108.6(19) . . ? H31A C31 H31C 109(3) . . ? H31B C31 H31C 110(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 N1 0.95(3) 1.69(3) 2.613(3) 161(3) . _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 27.55 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.258 _refine_diff_density_min -0.281 _refine_diff_density_rms 0.059