# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_eileen33 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H28 B Cl4 F15 N2' _chemical_formula_weight 890.18 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.2431(2) _cell_length_b 10.0854(2) _cell_length_c 25.7808(4) _cell_angle_alpha 90.00 _cell_angle_beta 96.352(2) _cell_angle_gamma 90.00 _cell_volume 3680.61(11) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 26032 _cell_measurement_theta_min 3.3930 _cell_measurement_theta_max 75.6449 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.606 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1792 _exptl_absorpt_coefficient_mu 3.891 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.68452 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'Nova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur, Atlas, Nova' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3543 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 43961 _diffrn_reflns_av_R_equivalents 0.0343 _diffrn_reflns_av_sigmaI/netI 0.0207 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 3.45 _diffrn_reflns_theta_max 75.83 _reflns_number_total 7638 _reflns_number_gt 6883 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'BRUKER XP' _computing_publication_material SHELXL-97 _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^)+(0.0418P)^2^+3.6286P] 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 7638 _refine_ls_number_parameters 504 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0479 _refine_ls_R_factor_gt 0.0434 _refine_ls_wR_factor_ref 0.1079 _refine_ls_wR_factor_gt 0.1044 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _refine_ls_shift/su_max 0.080 _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 B B 0.72087(14) 0.4746(2) 0.11650(8) 0.0212(4) Uani 1 1 d . . . N1 N 0.25545(11) 0.64825(15) 0.10319(6) 0.0217(3) Uani 1 1 d . . . N2 N 0.24968(11) 0.46589(16) 0.15015(6) 0.0227(3) Uani 1 1 d . . . F1 F 0.72941(7) 0.34570(11) 0.09425(4) 0.0247(2) Uani 1 1 d . . . F2 F 0.38088(7) 0.42581(11) 0.04709(4) 0.0245(2) Uani 1 1 d . . . F3 F 0.56522(7) 0.40187(11) 0.03924(4) 0.0239(2) Uani 1 1 d . . . F4 F 0.63163(8) 0.61008(15) 0.20395(5) 0.0432(3) Uani 1 1 d . . . F5 F 0.44808(8) 0.64719(15) 0.20752(5) 0.0406(3) Uani 1 1 d . . . F6 F 0.64769(9) 0.75327(12) 0.09469(6) 0.0398(3) Uani 1 1 d . . . F7 F 0.69802(10) 0.91450(13) 0.02148(6) 0.0441(3) Uani 1 1 d . . . F8 F 0.83767(10) 0.84599(14) -0.03716(5) 0.0432(3) Uani 1 1 d . . . F9 F 0.92561(9) 0.60691(14) -0.02120(5) 0.0375(3) Uani 1 1 d . . . F10 F 0.87810(8) 0.44307(11) 0.05275(5) 0.0302(3) Uani 1 1 d . . . F11 F 0.86623(9) 0.67631(12) 0.16592(5) 0.0341(3) Uani 1 1 d . . . F12 F 0.96798(9) 0.65000(15) 0.25799(5) 0.0453(3) Uani 1 1 d . . . F13 F 0.94717(11) 0.43271(17) 0.31841(5) 0.0523(4) Uani 1 1 d . . . F14 F 0.82023(12) 0.24150(15) 0.28420(5) 0.0527(4) Uani 1 1 d . . . F15 F 0.71311(11) 0.26928(13) 0.19351(5) 0.0434(3) Uani 1 1 d . . . Cl1 Cl 0.95940(6) 0.07299(12) 0.06749(4) 0.0949(4) Uani 1 1 d . . . Cl2 Cl 0.82670(4) -0.00644(7) 0.13865(3) 0.05254(17) Uani 1 1 d . . . Cl3 Cl 0.47745(5) 0.12459(6) 0.06373(3) 0.04896(16) Uani 1 1 d . . . Cl4 Cl 0.54400(5) 0.02993(10) 0.16756(3) 0.0657(2) Uani 1 1 d . . . C1 C 0.30756(12) 0.55193(18) 0.12901(7) 0.0207(3) Uani 1 1 d . . . C2 C 0.16086(13) 0.6211(2) 0.10787(7) 0.0256(4) Uani 1 1 d . . . C3 C 0.15732(13) 0.5090(2) 0.13645(7) 0.0263(4) Uani 1 1 d . . . C4 C 0.28955(15) 0.77292(18) 0.07667(7) 0.0272(4) Uani 1 1 d . . . C5 C 0.2435(2) 0.7748(3) 0.02032(10) 0.0602(8) Uani 1 1 d . . . H5A H 0.1748 0.7806 0.0200 0.090 Uiso 1 1 calc R . . H5B H 0.2598 0.6933 0.0026 0.090 Uiso 1 1 calc R . . H5C H 0.2664 0.8517 0.0022 0.090 Uiso 1 1 calc R . . C6 C 0.2655(2) 0.8915(2) 0.10920(10) 0.0441(6) Uani 1 1 d . . . H6A H 0.2854 0.9733 0.0930 0.066 Uiso 1 1 calc R . . H6B H 0.2984 0.8835 0.1445 0.066 Uiso 1 1 calc R . . H6C H 0.1972 0.8942 0.1110 0.066 Uiso 1 1 calc R . . C7 C 0.39563(19) 0.7773(2) 0.07290(12) 0.0479(6) Uani 1 1 d . . . H7A H 0.4111 0.8574 0.0541 0.072 Uiso 1 1 calc R . . H7B H 0.4143 0.6988 0.0541 0.072 Uiso 1 1 calc R . . H7C H 0.4297 0.7783 0.1081 0.072 Uiso 1 1 calc R . . C8 C 0.07580(15) 0.6988(2) 0.08573(10) 0.0398(5) Uani 1 1 d . . . H8A H 0.0574 0.6712 0.0496 0.060 Uiso 1 1 calc R . . H8B H 0.0910 0.7936 0.0866 0.060 Uiso 1 1 calc R . . H8C H 0.0235 0.6822 0.1066 0.060 Uiso 1 1 calc R . . C9 C 0.06810(15) 0.4448(3) 0.14993(10) 0.0423(5) Uani 1 1 d . . . H9A H 0.0591 0.4654 0.1862 0.063 Uiso 1 1 calc R . . H9B H 0.0727 0.3486 0.1457 0.063 Uiso 1 1 calc R . . H9C H 0.0143 0.4786 0.1267 0.063 Uiso 1 1 calc R . . C10 C 0.27599(15) 0.3476(2) 0.18611(8) 0.0296(4) Uani 1 1 d . . . C11 C 0.23983(16) 0.3771(2) 0.23830(8) 0.0359(5) Uani 1 1 d . . . H11A H 0.1706 0.3803 0.2337 0.054 Uiso 1 1 calc R . . H11B H 0.2648 0.4627 0.2515 0.054 Uiso 1 1 calc R . . H11C H 0.2608 0.3072 0.2633 0.054 Uiso 1 1 calc R . . C12 C 0.2353(3) 0.2235(3) 0.15969(12) 0.0769(12) Uani 1 1 d . . . H12A H 0.2520 0.1467 0.1821 0.115 Uiso 1 1 calc R . . H12B H 0.2610 0.2119 0.1263 0.115 Uiso 1 1 calc R . . H12C H 0.1664 0.2314 0.1536 0.115 Uiso 1 1 calc R . . C13 C 0.3828(2) 0.3272(3) 0.19878(13) 0.0627(9) Uani 1 1 d . . . H13A H 0.3945 0.2527 0.2231 0.094 Uiso 1 1 calc R . . H13B H 0.4113 0.4078 0.2148 0.094 Uiso 1 1 calc R . . H13C H 0.4109 0.3080 0.1666 0.094 Uiso 1 1 calc R . . C14 C 0.41004(12) 0.53413(18) 0.12798(7) 0.0217(3) Uani 1 1 d . . . C15 C 0.44348(12) 0.47011(17) 0.08626(7) 0.0195(3) Uani 1 1 d . . . C16 C 0.53917(13) 0.45574(17) 0.08328(7) 0.0199(3) Uani 1 1 d . . . C17 C 0.60778(13) 0.49740(18) 0.12274(7) 0.0219(3) Uani 1 1 d . . . C18 C 0.57177(14) 0.5605(2) 0.16409(8) 0.0282(4) Uani 1 1 d . . . C19 C 0.47712(14) 0.5810(2) 0.16672(7) 0.0282(4) Uani 1 1 d . . . C20 C 0.75602(12) 0.58510(18) 0.07571(7) 0.0222(3) Uani 1 1 d . . . C21 C 0.71564(13) 0.7091(2) 0.06608(8) 0.0270(4) Uani 1 1 d . . . C22 C 0.74117(14) 0.7964(2) 0.02892(8) 0.0305(4) Uani 1 1 d . . . C23 C 0.81170(14) 0.7619(2) -0.00093(8) 0.0302(4) Uani 1 1 d . . . C24 C 0.85546(13) 0.6410(2) 0.00730(7) 0.0272(4) Uani 1 1 d . . . C25 C 0.82814(12) 0.55698(18) 0.04524(7) 0.0228(4) Uani 1 1 d . . . C26 C 0.78568(13) 0.47204(19) 0.17369(7) 0.0231(4) Uani 1 1 d . . . C27 C 0.85141(13) 0.5654(2) 0.19333(7) 0.0253(4) Uani 1 1 d . . . C28 C 0.90557(14) 0.5546(2) 0.24118(8) 0.0313(4) Uani 1 1 d . . . C29 C 0.89561(15) 0.4449(2) 0.27181(8) 0.0354(5) Uani 1 1 d . . . C30 C 0.83109(17) 0.3489(2) 0.25450(8) 0.0353(5) Uani 1 1 d . . . C31 C 0.77767(15) 0.3645(2) 0.20683(8) 0.0297(4) Uani 1 1 d . . . C32 C 0.88931(16) 0.1254(2) 0.11496(10) 0.0413(5) Uani 1 1 d . . . H32A H 0.8442 0.1934 0.0998 0.050 Uiso 1 1 calc R . . H32B H 0.9299 0.1667 0.1442 0.050 Uiso 1 1 calc R . . C33 C 0.57704(17) 0.0838(2) 0.10746(10) 0.0411(5) Uani 1 1 d . . . H33A H 0.6133 0.0129 0.0921 0.049 Uiso 1 1 calc R . . H33B H 0.6185 0.1625 0.1131 0.049 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 B 0.0216(9) 0.0209(9) 0.0213(9) -0.0034(7) 0.0030(7) 0.0005(7) N1 0.0250(7) 0.0195(7) 0.0205(7) -0.0023(6) 0.0020(6) 0.0000(6) N2 0.0244(7) 0.0236(8) 0.0214(7) -0.0003(6) 0.0080(6) -0.0003(6) F1 0.0275(5) 0.0220(5) 0.0251(5) -0.0041(4) 0.0045(4) 0.0022(4) F2 0.0240(5) 0.0280(5) 0.0206(5) -0.0048(4) -0.0013(4) -0.0025(4) F3 0.0273(5) 0.0285(6) 0.0167(5) -0.0050(4) 0.0060(4) 0.0005(4) F4 0.0258(6) 0.0661(9) 0.0358(7) -0.0317(6) -0.0050(5) 0.0057(6) F5 0.0299(6) 0.0643(9) 0.0276(6) -0.0237(6) 0.0036(5) 0.0088(6) F6 0.0372(7) 0.0265(6) 0.0596(8) 0.0021(6) 0.0223(6) 0.0085(5) F7 0.0422(7) 0.0307(7) 0.0589(9) 0.0153(6) 0.0028(6) 0.0073(6) F8 0.0493(8) 0.0481(8) 0.0319(6) 0.0146(6) 0.0034(5) -0.0110(6) F9 0.0356(6) 0.0470(7) 0.0328(6) -0.0070(5) 0.0166(5) -0.0067(6) F10 0.0240(5) 0.0284(6) 0.0391(6) -0.0029(5) 0.0080(5) 0.0049(4) F11 0.0383(6) 0.0315(6) 0.0311(6) 0.0018(5) -0.0024(5) -0.0102(5) F12 0.0376(7) 0.0583(9) 0.0371(7) -0.0039(6) -0.0086(5) -0.0160(6) F13 0.0514(8) 0.0722(11) 0.0293(7) 0.0075(7) -0.0135(6) -0.0012(7) F14 0.0820(11) 0.0436(8) 0.0306(7) 0.0143(6) -0.0026(7) -0.0050(7) F15 0.0619(9) 0.0359(7) 0.0310(6) 0.0039(5) -0.0008(6) -0.0196(6) Cl1 0.0716(5) 0.1303(8) 0.0928(6) 0.0714(6) 0.0535(5) 0.0591(6) Cl2 0.0424(3) 0.0577(4) 0.0578(4) 0.0183(3) 0.0069(3) -0.0093(3) Cl3 0.0517(3) 0.0330(3) 0.0578(4) 0.0113(2) -0.0135(3) -0.0117(2) Cl4 0.0577(4) 0.1005(6) 0.0373(3) 0.0059(3) -0.0022(3) -0.0039(4) C1 0.0232(8) 0.0211(8) 0.0182(8) -0.0016(6) 0.0043(6) -0.0002(7) C2 0.0221(9) 0.0296(10) 0.0248(9) -0.0067(7) 0.0008(7) 0.0019(7) C3 0.0224(9) 0.0329(10) 0.0243(9) -0.0062(8) 0.0059(7) -0.0028(7) C4 0.0393(11) 0.0183(9) 0.0238(9) 0.0006(7) 0.0031(8) -0.0018(8) C5 0.094(2) 0.0561(17) 0.0271(12) 0.0105(11) -0.0079(13) -0.0319(16) C6 0.0661(16) 0.0215(10) 0.0478(13) -0.0036(9) 0.0201(12) 0.0020(10) C7 0.0499(14) 0.0261(11) 0.0710(18) 0.0117(11) 0.0213(12) -0.0049(10) C8 0.0283(10) 0.0432(13) 0.0453(13) -0.0051(10) -0.0066(9) 0.0089(9) C9 0.0274(10) 0.0563(15) 0.0449(13) 0.0008(11) 0.0118(9) -0.0099(10) C10 0.0425(11) 0.0230(9) 0.0253(9) 0.0040(7) 0.0131(8) 0.0020(8) C11 0.0430(12) 0.0428(12) 0.0232(10) 0.0057(9) 0.0096(8) 0.0054(10) C12 0.161(4) 0.0242(12) 0.0415(15) -0.0015(11) -0.0093(19) -0.0096(17) C13 0.0501(15) 0.075(2) 0.0692(18) 0.0506(16) 0.0323(14) 0.0308(14) C14 0.0213(8) 0.0248(9) 0.0195(8) 0.0005(7) 0.0042(6) 0.0001(7) C15 0.0223(8) 0.0194(8) 0.0167(8) -0.0001(6) 0.0009(6) -0.0033(6) C16 0.0252(8) 0.0192(8) 0.0163(8) -0.0012(6) 0.0059(6) -0.0006(7) C17 0.0227(8) 0.0219(9) 0.0216(8) -0.0018(7) 0.0041(7) -0.0006(7) C18 0.0242(9) 0.0366(11) 0.0230(9) -0.0112(8) -0.0009(7) -0.0005(8) C19 0.0285(9) 0.0362(10) 0.0205(9) -0.0098(8) 0.0047(7) 0.0040(8) C20 0.0210(8) 0.0238(9) 0.0212(8) -0.0024(7) -0.0001(6) -0.0002(7) C21 0.0228(9) 0.0269(10) 0.0319(10) -0.0013(8) 0.0050(7) 0.0017(7) C22 0.0287(9) 0.0260(10) 0.0353(10) 0.0048(8) -0.0033(8) 0.0015(8) C23 0.0318(10) 0.0350(11) 0.0230(9) 0.0052(8) -0.0010(7) -0.0080(8) C24 0.0232(9) 0.0368(11) 0.0217(9) -0.0059(8) 0.0030(7) -0.0050(8) C25 0.0200(8) 0.0238(9) 0.0236(8) -0.0043(7) -0.0011(6) 0.0000(7) C26 0.0220(8) 0.0253(9) 0.0223(8) -0.0020(7) 0.0045(7) 0.0031(7) C27 0.0237(9) 0.0273(9) 0.0253(9) -0.0005(7) 0.0040(7) 0.0026(7) C28 0.0230(9) 0.0410(12) 0.0294(10) -0.0065(9) 0.0006(7) -0.0015(8) C29 0.0334(10) 0.0492(13) 0.0225(9) 0.0008(9) -0.0028(8) 0.0058(9) C30 0.0465(12) 0.0334(11) 0.0261(10) 0.0055(8) 0.0040(9) 0.0032(9) C31 0.0360(10) 0.0282(10) 0.0249(9) -0.0018(8) 0.0036(8) -0.0026(8) C32 0.0346(11) 0.0350(12) 0.0538(14) 0.0088(10) 0.0027(10) 0.0017(9) C33 0.0377(12) 0.0373(12) 0.0476(13) -0.0019(10) 0.0013(10) 0.0029(9) _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 B F1 1.431(2) . ? B C20 1.648(3) . ? B C26 1.651(3) . ? B C17 1.652(3) . ? N1 C1 1.352(2) . ? N1 C2 1.393(2) . ? N1 C4 1.535(2) . ? N2 C1 1.352(2) . ? N2 C3 1.394(2) . ? N2 C10 1.532(2) . ? F2 C15 1.347(2) . ? F3 C16 1.3473(19) . ? F4 C18 1.356(2) . ? F5 C19 1.349(2) . ? F6 C21 1.355(2) . ? F7 C22 1.344(2) . ? F8 C23 1.343(2) . ? F9 C24 1.349(2) . ? F10 C25 1.354(2) . ? F11 C27 1.352(2) . ? F12 C28 1.348(2) . ? F13 C29 1.342(2) . ? F14 C30 1.345(3) . ? F15 C31 1.348(2) . ? Cl1 C32 1.745(3) . ? Cl2 C32 1.749(2) . ? Cl3 C33 1.760(2) . ? Cl4 C33 1.755(3) . ? C1 C14 1.474(2) . ? C2 C3 1.353(3) . ? C2 C8 1.501(3) . ? C3 C9 1.501(3) . ? C4 C6 1.522(3) . ? C4 C7 1.525(3) . ? C4 C5 1.526(3) . ? C10 C12 1.509(3) . ? C10 C11 1.523(3) . ? C10 C13 1.534(3) . ? C14 C15 1.384(2) . ? C14 C19 1.387(3) . ? C15 C16 1.381(2) . ? C16 C17 1.395(3) . ? C17 C18 1.388(3) . ? C18 C19 1.373(3) . ? C20 C21 1.387(3) . ? C20 C25 1.390(3) . ? C21 C22 1.379(3) . ? C22 C23 1.376(3) . ? C23 C24 1.375(3) . ? C24 C25 1.382(3) . ? C26 C27 1.383(3) . ? C26 C31 1.393(3) . ? C27 C28 1.385(3) . ? C28 C29 1.376(3) . ? C29 C30 1.375(3) . ? C30 C31 1.381(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 F1 B C20 108.25(14) . . ? F1 B C26 106.26(15) . . ? C20 B C26 113.65(15) . . ? F1 B C17 107.01(14) . . ? C20 B C17 109.64(15) . . ? C26 B C17 111.71(14) . . ? C1 N1 C2 107.44(15) . . ? C1 N1 C4 128.61(16) . . ? C2 N1 C4 123.79(16) . . ? C1 N2 C3 107.33(16) . . ? C1 N2 C10 128.65(16) . . ? C3 N2 C10 123.88(16) . . ? N1 C1 N2 109.48(15) . . ? N1 C1 C14 124.72(16) . . ? N2 C1 C14 125.32(16) . . ? C3 C2 N1 107.81(16) . . ? C3 C2 C8 124.44(19) . . ? N1 C2 C8 127.74(19) . . ? C2 C3 N2 107.93(16) . . ? C2 C3 C9 124.75(19) . . ? N2 C3 C9 127.32(19) . . ? C6 C4 C7 107.30(19) . . ? C6 C4 C5 114.6(2) . . ? C7 C4 C5 105.3(2) . . ? C6 C4 N1 107.27(16) . . ? C7 C4 N1 114.60(16) . . ? C5 C4 N1 108.07(17) . . ? C12 C10 C11 114.2(2) . . ? C12 C10 N2 108.46(18) . . ? C11 C10 N2 107.37(16) . . ? C12 C10 C13 107.9(3) . . ? C11 C10 C13 105.2(2) . . ? N2 C10 C13 113.81(17) . . ? C15 C14 C19 116.74(16) . . ? C15 C14 C1 119.84(16) . . ? C19 C14 C1 123.41(16) . . ? F2 C15 C16 119.92(15) . . ? F2 C15 C14 118.76(15) . . ? C16 C15 C14 121.26(16) . . ? F3 C16 C15 117.04(15) . . ? F3 C16 C17 119.99(15) . . ? C15 C16 C17 122.94(16) . . ? C18 C17 C16 114.18(16) . . ? C18 C17 B 125.86(16) . . ? C16 C17 B 119.92(15) . . ? F4 C18 C19 116.46(16) . . ? F4 C18 C17 119.77(17) . . ? C19 C18 C17 123.74(17) . . ? F5 C19 C18 120.04(17) . . ? F5 C19 C14 118.94(17) . . ? C18 C19 C14 121.02(17) . . ? C21 C20 C25 113.62(17) . . ? C21 C20 B 125.07(16) . . ? C25 C20 B 121.23(16) . . ? F6 C21 C22 115.28(17) . . ? F6 C21 C20 120.38(17) . . ? C22 C21 C20 124.32(18) . . ? F7 C22 C23 119.64(19) . . ? F7 C22 C21 120.89(19) . . ? C23 C22 C21 119.47(19) . . ? F8 C23 C24 120.78(19) . . ? F8 C23 C22 120.25(19) . . ? C24 C23 C22 118.96(18) . . ? F9 C24 C23 119.51(18) . . ? F9 C24 C25 120.84(18) . . ? C23 C24 C25 119.64(18) . . ? F10 C25 C24 115.90(16) . . ? F10 C25 C20 120.14(17) . . ? C24 C25 C20 123.94(18) . . ? C27 C26 C31 113.77(17) . . ? C27 C26 B 127.25(17) . . ? C31 C26 B 118.96(17) . . ? F11 C27 C26 120.67(17) . . ? F11 C27 C28 115.22(18) . . ? C26 C27 C28 124.10(19) . . ? F12 C28 C29 119.71(18) . . ? F12 C28 C27 120.9(2) . . ? C29 C28 C27 119.42(19) . . ? F13 C29 C30 120.4(2) . . ? F13 C29 C28 120.4(2) . . ? C30 C29 C28 119.20(19) . . ? F14 C30 C29 119.80(19) . . ? F14 C30 C31 120.8(2) . . ? C29 C30 C31 119.4(2) . . ? F15 C31 C30 116.01(18) . . ? F15 C31 C26 119.89(18) . . ? C30 C31 C26 124.07(19) . . ? Cl1 C32 Cl2 111.58(14) . . ? Cl4 C33 Cl3 111.22(14) . . ? 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 C2 N1 C1 N2 -0.6(2) . . . . ? C4 N1 C1 N2 174.84(16) . . . . ? C2 N1 C1 C14 171.82(17) . . . . ? C4 N1 C1 C14 -12.8(3) . . . . ? C3 N2 C1 N1 0.8(2) . . . . ? C10 N2 C1 N1 -174.92(16) . . . . ? C3 N2 C1 C14 -171.50(17) . . . . ? C10 N2 C1 C14 12.8(3) . . . . ? C1 N1 C2 C3 0.1(2) . . . . ? C4 N1 C2 C3 -175.60(16) . . . . ? C1 N1 C2 C8 -179.68(19) . . . . ? C4 N1 C2 C8 4.6(3) . . . . ? N1 C2 C3 N2 0.4(2) . . . . ? C8 C2 C3 N2 -179.81(18) . . . . ? N1 C2 C3 C9 -179.19(19) . . . . ? C8 C2 C3 C9 0.6(3) . . . . ? C1 N2 C3 C2 -0.8(2) . . . . ? C10 N2 C3 C2 175.23(16) . . . . ? C1 N2 C3 C9 178.8(2) . . . . ? C10 N2 C3 C9 -5.2(3) . . . . ? C1 N1 C4 C6 -109.8(2) . . . . ? C2 N1 C4 C6 64.9(2) . . . . ? C1 N1 C4 C7 9.2(3) . . . . ? C2 N1 C4 C7 -176.12(19) . . . . ? C1 N1 C4 C5 126.2(2) . . . . ? C2 N1 C4 C5 -59.1(3) . . . . ? C1 N2 C10 C12 -120.2(3) . . . . ? C3 N2 C10 C12 64.7(3) . . . . ? C1 N2 C10 C11 115.9(2) . . . . ? C3 N2 C10 C11 -59.2(2) . . . . ? C1 N2 C10 C13 -0.1(3) . . . . ? C3 N2 C10 C13 -175.2(2) . . . . ? N1 C1 C14 C15 -80.9(2) . . . . ? N2 C1 C14 C15 90.3(2) . . . . ? N1 C1 C14 C19 97.8(2) . . . . ? N2 C1 C14 C19 -91.0(2) . . . . ? C19 C14 C15 F2 -178.41(16) . . . . ? C1 C14 C15 F2 0.4(3) . . . . ? C19 C14 C15 C16 -0.9(3) . . . . ? C1 C14 C15 C16 177.82(16) . . . . ? F2 C15 C16 F3 2.8(2) . . . . ? C14 C15 C16 F3 -174.66(16) . . . . ? F2 C15 C16 C17 -178.97(16) . . . . ? C14 C15 C16 C17 3.6(3) . . . . ? F3 C16 C17 C18 175.16(17) . . . . ? C15 C16 C17 C18 -3.0(3) . . . . ? F3 C16 C17 B -2.7(3) . . . . ? C15 C16 C17 B 179.11(16) . . . . ? F1 B C17 C18 141.67(19) . . . . ? C20 B C17 C18 -101.1(2) . . . . ? C26 B C17 C18 25.8(3) . . . . ? F1 B C17 C16 -40.8(2) . . . . ? C20 B C17 C16 76.4(2) . . . . ? C26 B C17 C16 -156.66(16) . . . . ? C16 C17 C18 F4 -177.49(18) . . . . ? B C17 C18 F4 0.2(3) . . . . ? C16 C17 C18 C19 0.1(3) . . . . ? B C17 C18 C19 177.8(2) . . . . ? F4 C18 C19 F5 -0.1(3) . . . . ? C17 C18 C19 F5 -177.75(19) . . . . ? F4 C18 C19 C14 -179.92(19) . . . . ? C17 C18 C19 C14 2.4(3) . . . . ? C15 C14 C19 F5 178.25(18) . . . . ? C1 C14 C19 F5 -0.5(3) . . . . ? C15 C14 C19 C18 -1.9(3) . . . . ? C1 C14 C19 C18 179.35(19) . . . . ? F1 B C20 C21 142.77(17) . . . . ? C26 B C20 C21 -99.4(2) . . . . ? C17 B C20 C21 26.4(2) . . . . ? F1 B C20 C25 -33.8(2) . . . . ? C26 B C20 C25 84.0(2) . . . . ? C17 B C20 C25 -150.16(16) . . . . ? C25 C20 C21 F6 -176.60(17) . . . . ? B C20 C21 F6 6.6(3) . . . . ? C25 C20 C21 C22 2.0(3) . . . . ? B C20 C21 C22 -174.80(18) . . . . ? F6 C21 C22 F7 -2.1(3) . . . . ? C20 C21 C22 F7 179.30(18) . . . . ? F6 C21 C22 C23 177.99(18) . . . . ? C20 C21 C22 C23 -0.6(3) . . . . ? F7 C22 C23 F8 0.3(3) . . . . ? C21 C22 C23 F8 -179.76(18) . . . . ? F7 C22 C23 C24 179.72(18) . . . . ? C21 C22 C23 C24 -0.3(3) . . . . ? F8 C23 C24 F9 0.3(3) . . . . ? C22 C23 C24 F9 -179.06(18) . . . . ? F8 C23 C24 C25 179.26(17) . . . . ? C22 C23 C24 C25 -0.2(3) . . . . ? F9 C24 C25 F10 2.3(3) . . . . ? C23 C24 C25 F10 -176.61(16) . . . . ? F9 C24 C25 C20 -179.41(16) . . . . ? C23 C24 C25 C20 1.7(3) . . . . ? C21 C20 C25 F10 175.75(16) . . . . ? B C20 C25 F10 -7.3(3) . . . . ? C21 C20 C25 C24 -2.5(3) . . . . ? B C20 C25 C24 174.42(17) . . . . ? F1 B C26 C27 131.96(18) . . . . ? C20 B C26 C27 13.0(3) . . . . ? C17 B C26 C27 -111.7(2) . . . . ? F1 B C26 C31 -46.3(2) . . . . ? C20 B C26 C31 -165.24(17) . . . . ? C17 B C26 C31 70.1(2) . . . . ? C31 C26 C27 F11 -179.10(17) . . . . ? B C26 C27 F11 2.6(3) . . . . ? C31 C26 C27 C28 0.5(3) . . . . ? B C26 C27 C28 -177.87(18) . . . . ? F11 C27 C28 F12 0.0(3) . . . . ? C26 C27 C28 F12 -179.60(18) . . . . ? F11 C27 C28 C29 -179.80(18) . . . . ? C26 C27 C28 C29 0.6(3) . . . . ? F12 C28 C29 F13 0.5(3) . . . . ? C27 C28 C29 F13 -179.76(19) . . . . ? F12 C28 C29 C30 179.4(2) . . . . ? C27 C28 C29 C30 -0.8(3) . . . . ? F13 C29 C30 F14 -0.7(3) . . . . ? C28 C29 C30 F14 -179.6(2) . . . . ? F13 C29 C30 C31 178.9(2) . . . . ? C28 C29 C30 C31 0.0(3) . . . . ? F14 C30 C31 F15 2.3(3) . . . . ? C29 C30 C31 F15 -177.2(2) . . . . ? F14 C30 C31 C26 -179.2(2) . . . . ? C29 C30 C31 C26 1.2(3) . . . . ? C27 C26 C31 F15 177.00(18) . . . . ? B C26 C31 F15 -4.5(3) . . . . ? C27 C26 C31 C30 -1.4(3) . . . . ? B C26 C31 C30 177.10(19) . . . . ? 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 C32 H32A F1 0.99 2.24 3.184(3) 159.9 . C33 H33B F1 0.99 2.51 3.459(3) 159.7 . C33 H33A F7 0.99 2.50 3.412(3) 153.3 1_545 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 75.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.861 _refine_diff_density_min -1.206 _refine_diff_density_rms 0.056 _iucr_refine_instructions_details ; TITL eileen33 in P2(1)/c CELL 1.54184 14.2431 10.0854 25.7808 90.000 96.352 90.000 ZERR 4.00 0.0002 0.0002 0.0004 0.000 0.002 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H B N F CL UNIT 132 112 4 8 60 16 SIZE 0.17 0.04 0.03 TEMP -173 ACTA 150 CONF FMAP 2 PLAN 10 L.S. 4 HTAB C32 F1 HTAB C33 F1 EQIV_$1 +x, -1+y, +z HTAB C33 F7_$1 WGHT 0.041800 3.628600 FVAR 3.60607 B 3 0.720870 0.474580 0.116501 11.00000 0.02159 0.02089 = 0.02130 -0.00344 0.00304 0.00054 N1 4 0.255445 0.648252 0.103192 11.00000 0.02500 0.01951 = 0.02049 -0.00234 0.00200 0.00001 N2 4 0.249685 0.465886 0.150152 11.00000 0.02439 0.02364 = 0.02143 -0.00026 0.00798 -0.00028 F1 5 0.729412 0.345699 0.094251 11.00000 0.02753 0.02200 = 0.02505 -0.00407 0.00446 0.00221 F2 5 0.380878 0.425813 0.047085 11.00000 0.02405 0.02802 = 0.02058 -0.00478 -0.00133 -0.00250 F3 5 0.565221 0.401866 0.039239 11.00000 0.02733 0.02847 = 0.01668 -0.00505 0.00598 0.00045 F4 5 0.631633 0.610082 0.203952 11.00000 0.02578 0.06608 = 0.03580 -0.03168 -0.00503 0.00568 F5 5 0.448075 0.647192 0.207515 11.00000 0.02986 0.06431 = 0.02759 -0.02368 0.00358 0.00875 F6 5 0.647693 0.753268 0.094687 11.00000 0.03717 0.02648 = 0.05965 0.00205 0.02232 0.00854 F7 5 0.698023 0.914497 0.021481 11.00000 0.04215 0.03066 = 0.05887 0.01528 0.00281 0.00727 F8 5 0.837673 0.845991 -0.037161 11.00000 0.04927 0.04810 = 0.03194 0.01461 0.00339 -0.01100 F9 5 0.925611 0.606907 -0.021204 11.00000 0.03561 0.04705 = 0.03280 -0.00702 0.01663 -0.00667 F10 5 0.878102 0.443073 0.052747 11.00000 0.02400 0.02842 = 0.03908 -0.00287 0.00798 0.00486 F11 5 0.866234 0.676306 0.165922 11.00000 0.03828 0.03153 = 0.03108 0.00176 -0.00243 -0.01021 F12 5 0.967982 0.649996 0.257994 11.00000 0.03760 0.05831 = 0.03710 -0.00390 -0.00856 -0.01605 F13 5 0.947167 0.432707 0.318405 11.00000 0.05144 0.07225 = 0.02927 0.00751 -0.01354 -0.00118 F14 5 0.820226 0.241495 0.284200 11.00000 0.08203 0.04360 = 0.03061 0.01428 -0.00260 -0.00502 F15 5 0.713114 0.269277 0.193511 11.00000 0.06190 0.03589 = 0.03101 0.00386 -0.00081 -0.01961 CL1 6 0.959401 0.072993 0.067490 11.00000 0.07164 0.13030 = 0.09279 0.07142 0.05347 0.05912 CL2 6 0.826701 -0.006440 0.138653 11.00000 0.04243 0.05769 = 0.05778 0.01826 0.00685 -0.00929 CL3 6 0.477446 0.124589 0.063735 11.00000 0.05168 0.03298 = 0.05784 0.01129 -0.01347 -0.01174 CL4 6 0.544004 0.029932 0.167556 11.00000 0.05767 0.10054 = 0.03734 0.00590 -0.00223 -0.00386 C1 1 0.307557 0.551926 0.129005 11.00000 0.02320 0.02105 = 0.01817 -0.00162 0.00435 -0.00025 C2 1 0.160864 0.621108 0.107866 11.00000 0.02211 0.02958 = 0.02484 -0.00669 0.00080 0.00185 C3 1 0.157323 0.509033 0.136449 11.00000 0.02244 0.03287 = 0.02431 -0.00620 0.00592 -0.00280 C4 1 0.289549 0.772918 0.076671 11.00000 0.03933 0.01835 = 0.02378 0.00056 0.00311 -0.00184 C5 1 0.243509 0.774794 0.020325 11.00000 0.09421 0.05611 = 0.02715 0.01055 -0.00790 -0.03192 AFIX 137 H5A 2 0.174759 0.780622 0.019966 11.00000 -1.50000 H5B 2 0.259777 0.693288 0.002650 11.00000 -1.50000 H5C 2 0.266431 0.851676 0.002181 11.00000 -1.50000 AFIX 0 C6 1 0.265506 0.891540 0.109198 11.00000 0.06609 0.02149 = 0.04785 -0.00362 0.02012 0.00199 AFIX 137 H6A 2 0.285447 0.973277 0.093019 11.00000 -1.50000 H6B 2 0.298417 0.883523 0.144505 11.00000 -1.50000 H6C 2 0.197169 0.894218 0.111018 11.00000 -1.50000 AFIX 0 C7 1 0.395632 0.777259 0.072904 11.00000 0.04987 0.02607 = 0.07102 0.01167 0.02129 -0.00485 AFIX 137 H7A 2 0.411085 0.857439 0.054122 11.00000 -1.50000 H7B 2 0.414304 0.698827 0.054084 11.00000 -1.50000 H7C 2 0.429662 0.778300 0.108085 11.00000 -1.50000 AFIX 0 C8 1 0.075800 0.698767 0.085728 11.00000 0.02834 0.04321 = 0.04534 -0.00508 -0.00662 0.00891 AFIX 137 H8A 2 0.057405 0.671236 0.049576 11.00000 -1.50000 H8B 2 0.090998 0.793567 0.086599 11.00000 -1.50000 H8C 2 0.023474 0.682189 0.106559 11.00000 -1.50000 AFIX 0 C9 1 0.068105 0.444820 0.149927 11.00000 0.02739 0.05628 = 0.04494 0.00075 0.01184 -0.00993 AFIX 137 H9A 2 0.059080 0.465388 0.186195 11.00000 -1.50000 H9B 2 0.072674 0.348551 0.145692 11.00000 -1.50000 H9C 2 0.014305 0.478594 0.126694 11.00000 -1.50000 AFIX 0 C10 1 0.275991 0.347566 0.186105 11.00000 0.04250 0.02298 = 0.02533 0.00401 0.01309 0.00202 C11 1 0.239827 0.377057 0.238305 11.00000 0.04295 0.04277 = 0.02323 0.00567 0.00961 0.00537 AFIX 137 H11A 2 0.170639 0.380314 0.233695 11.00000 -1.50000 H11B 2 0.264751 0.462685 0.251473 11.00000 -1.50000 H11C 2 0.260813 0.307155 0.263344 11.00000 -1.50000 AFIX 0 C12 1 0.235276 0.223504 0.159691 11.00000 0.16059 0.02419 = 0.04146 -0.00151 -0.00932 -0.00955 AFIX 137 H12A 2 0.252006 0.146671 0.182096 11.00000 -1.50000 H12B 2 0.261023 0.211880 0.126273 11.00000 -1.50000 H12C 2 0.166364 0.231409 0.153555 11.00000 -1.50000 AFIX 0 C13 1 0.382825 0.327181 0.198785 11.00000 0.05012 0.07450 = 0.06918 0.05057 0.03227 0.03079 AFIX 137 H13A 2 0.394528 0.252700 0.223053 11.00000 -1.50000 H13B 2 0.411318 0.407830 0.214838 11.00000 -1.50000 H13C 2 0.410860 0.307994 0.166562 11.00000 -1.50000 AFIX 0 C14 1 0.410035 0.534133 0.127984 11.00000 0.02135 0.02482 = 0.01952 0.00047 0.00425 0.00008 C15 1 0.443485 0.470106 0.086260 11.00000 0.02228 0.01941 = 0.01666 -0.00009 0.00086 -0.00333 C16 1 0.539166 0.455737 0.083281 11.00000 0.02517 0.01916 = 0.01626 -0.00124 0.00595 -0.00064 C17 1 0.607781 0.497400 0.122739 11.00000 0.02268 0.02190 = 0.02162 -0.00182 0.00408 -0.00065 C18 1 0.571772 0.560485 0.164093 11.00000 0.02422 0.03657 = 0.02301 -0.01116 -0.00089 -0.00054 C19 1 0.477120 0.580966 0.166725 11.00000 0.02847 0.03618 = 0.02047 -0.00985 0.00468 0.00401 C20 1 0.756025 0.585104 0.075706 11.00000 0.02100 0.02383 = 0.02119 -0.00244 -0.00005 -0.00020 C21 1 0.715642 0.709096 0.066078 11.00000 0.02275 0.02695 = 0.03188 -0.00127 0.00496 0.00172 C22 1 0.741166 0.796421 0.028921 11.00000 0.02870 0.02597 = 0.03535 0.00484 -0.00327 0.00152 C23 1 0.811700 0.761948 -0.000929 11.00000 0.03179 0.03503 = 0.02296 0.00524 -0.00098 -0.00797 C24 1 0.855463 0.641024 0.007299 11.00000 0.02320 0.03681 = 0.02165 -0.00592 0.00302 -0.00503 C25 1 0.828142 0.556980 0.045240 11.00000 0.02004 0.02384 = 0.02362 -0.00425 -0.00113 0.00004 C26 1 0.785677 0.472044 0.173692 11.00000 0.02199 0.02533 = 0.02232 -0.00198 0.00450 0.00307 C27 1 0.851409 0.565354 0.193331 11.00000 0.02373 0.02726 = 0.02525 -0.00052 0.00399 0.00259 C28 1 0.905574 0.554643 0.241183 11.00000 0.02303 0.04096 = 0.02942 -0.00652 0.00058 -0.00153 C29 1 0.895612 0.444851 0.271814 11.00000 0.03341 0.04917 = 0.02245 0.00078 -0.00277 0.00583 C30 1 0.831094 0.348875 0.254503 11.00000 0.04653 0.03338 = 0.02611 0.00554 0.00404 0.00315 C31 1 0.777667 0.364520 0.206834 11.00000 0.03595 0.02820 = 0.02486 -0.00178 0.00361 -0.00263 C32 1 0.889307 0.125445 0.114959 11.00000 0.03461 0.03503 = 0.05383 0.00876 0.00272 0.00170 AFIX 23 H32A 2 0.844182 0.193447 0.099831 11.00000 -1.20000 H32B 2 0.929908 0.166670 0.144228 11.00000 -1.20000 AFIX 0 C33 1 0.577040 0.083827 0.107458 11.00000 0.03769 0.03727 = 0.04756 -0.00194 0.00133 0.00290 AFIX 23 H33A 2 0.613311 0.012921 0.092109 11.00000 -1.20000 H33B 2 0.618459 0.162519 0.113113 11.00000 -1.20000 HKLF 4 ; _database_code_depnum_ccdc_archive 'CCDC 963622' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_eileen42 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H20 N2 O2' _chemical_formula_weight 224.30 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P c c n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-x, y+1/2, -z+1/2' 'x+1/2, -y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'x, -y-1/2, z-1/2' '-x-1/2, y, z-1/2' _cell_length_a 13.7743(3) _cell_length_b 13.7329(4) _cell_length_c 12.8256(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2426.10(10) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 26433 _cell_measurement_theta_min 3.2154 _cell_measurement_theta_max 75.9390 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.228 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976 _exptl_absorpt_coefficient_mu 0.675 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.35282 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'Nova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur, Atlas, Nova' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3543 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 52765 _diffrn_reflns_av_R_equivalents 0.0752 _diffrn_reflns_av_sigmaI/netI 0.0173 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 4.55 _diffrn_reflns_theta_max 76.13 _reflns_number_total 2535 _reflns_number_gt 2357 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker XP' _computing_publication_material SHELXL-97 _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^)+(0.0660P)^2^+0.6647P] 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 2535 _refine_ls_number_parameters 151 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0423 _refine_ls_R_factor_gt 0.0404 _refine_ls_wR_factor_ref 0.1131 _refine_ls_wR_factor_gt 0.1113 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.30054(6) 0.90049(6) 0.41632(7) 0.0209(2) Uani 1 1 d . . . N2 N 0.44310(6) 0.83685(6) 0.44569(7) 0.0213(2) Uani 1 1 d . . . O1 O 0.38977(6) 0.86121(6) 0.19268(6) 0.0297(2) Uani 1 1 d . . . O2 O 0.47466(6) 0.98719(7) 0.25959(7) 0.0339(2) Uani 1 1 d . . . C1 C 0.38889(7) 0.88484(8) 0.37444(8) 0.0214(2) Uani 1 1 d . . . C2 C 0.29892(8) 0.86133(8) 0.51584(8) 0.0231(2) Uani 1 1 d . . . H2 H 0.2455 0.8621 0.5627 0.028 Uiso 1 1 calc R . . C3 C 0.38680(8) 0.82193(8) 0.53395(9) 0.0235(2) Uani 1 1 d . . . H3 H 0.4067 0.7897 0.5959 0.028 Uiso 1 1 calc R . . C4 C 0.21215(8) 0.94433(8) 0.36389(8) 0.0225(2) Uani 1 1 d . . . C5 C 0.16881(8) 0.86586(8) 0.29413(9) 0.0264(3) Uani 1 1 d . . . H5A H 0.1120 0.8921 0.2577 0.040 Uiso 1 1 calc R . . H5B H 0.1492 0.8100 0.3368 0.040 Uiso 1 1 calc R . . H5C H 0.2174 0.8450 0.2430 0.040 Uiso 1 1 calc R . . C6 C 0.24071(9) 1.03475(8) 0.30148(10) 0.0292(3) Uani 1 1 d . . . H6A H 0.2807 1.0154 0.2418 0.044 Uiso 1 1 calc R . . H6B H 0.2777 1.0792 0.3461 0.044 Uiso 1 1 calc R . . H6C H 0.1820 1.0677 0.2765 0.044 Uiso 1 1 calc R . . C7 C 0.13879(8) 0.97363(9) 0.44755(9) 0.0291(3) Uani 1 1 d . . . H7A H 0.0819 1.0032 0.4144 0.044 Uiso 1 1 calc R . . H7B H 0.1687 1.0207 0.4951 0.044 Uiso 1 1 calc R . . H7C H 0.1188 0.9158 0.4868 0.044 Uiso 1 1 calc R . . C8 C 0.54989(8) 0.81299(8) 0.43931(9) 0.0241(2) Uani 1 1 d . . . C9 C 0.57641(9) 0.74701(10) 0.53108(10) 0.0333(3) Uani 1 1 d . . . H9A H 0.5670 0.7825 0.5966 0.050 Uiso 1 1 calc R . . H9B H 0.6445 0.7270 0.5250 0.050 Uiso 1 1 calc R . . H9C H 0.5347 0.6892 0.5304 0.050 Uiso 1 1 calc R . . C10 C 0.57229(8) 0.76010(9) 0.33707(10) 0.0309(3) Uani 1 1 d . . . H10A H 0.5362 0.6987 0.3347 0.046 Uiso 1 1 calc R . . H10B H 0.6421 0.7466 0.3330 0.046 Uiso 1 1 calc R . . H10C H 0.5530 0.8012 0.2781 0.046 Uiso 1 1 calc R . . C11 C 0.60541(8) 0.90875(9) 0.44884(10) 0.0285(3) Uani 1 1 d . . . H11A H 0.5876 0.9518 0.3910 0.043 Uiso 1 1 calc R . . H11B H 0.6753 0.8958 0.4465 0.043 Uiso 1 1 calc R . . H11C H 0.5890 0.9402 0.5151 0.043 Uiso 1 1 calc R . . C12 C 0.42146(8) 0.91465(8) 0.26313(8) 0.0241(2) 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 N1 0.0192(4) 0.0220(4) 0.0216(4) 0.0003(3) -0.0014(3) -0.0006(3) N2 0.0192(4) 0.0229(4) 0.0217(4) 0.0004(3) -0.0002(3) -0.0009(3) O1 0.0312(4) 0.0360(5) 0.0220(4) -0.0020(3) -0.0005(3) 0.0018(3) O2 0.0300(4) 0.0392(5) 0.0327(5) 0.0090(4) -0.0005(3) -0.0107(4) C1 0.0205(5) 0.0213(5) 0.0225(5) -0.0009(4) -0.0010(4) -0.0024(4) C2 0.0228(5) 0.0252(5) 0.0213(5) 0.0012(4) 0.0008(4) -0.0016(4) C3 0.0238(5) 0.0258(5) 0.0208(5) 0.0020(4) 0.0001(4) -0.0008(4) C4 0.0195(5) 0.0246(5) 0.0235(5) 0.0015(4) -0.0030(4) 0.0014(4) C5 0.0229(5) 0.0284(6) 0.0278(6) -0.0013(4) -0.0043(4) -0.0004(4) C6 0.0280(6) 0.0268(5) 0.0328(6) 0.0065(4) -0.0052(5) -0.0004(4) C7 0.0246(6) 0.0342(6) 0.0286(6) -0.0015(5) -0.0015(4) 0.0065(5) C8 0.0173(5) 0.0273(5) 0.0277(5) 0.0000(4) -0.0010(4) -0.0002(4) C9 0.0223(5) 0.0374(6) 0.0401(7) 0.0102(5) -0.0021(5) 0.0034(5) C10 0.0222(5) 0.0344(6) 0.0362(6) -0.0081(5) 0.0007(5) 0.0018(5) C11 0.0226(5) 0.0309(6) 0.0319(6) -0.0022(5) -0.0020(4) -0.0038(4) C12 0.0202(5) 0.0298(6) 0.0225(5) 0.0031(4) 0.0012(4) 0.0022(4) _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 C1 1.3475(14) . ? N1 C2 1.3853(14) . ? N1 C4 1.5155(13) . ? N2 C1 1.3517(14) . ? N2 C3 1.3873(14) . ? N2 C8 1.5092(14) . ? O1 C12 1.2432(14) . ? O2 C12 1.2375(14) . ? C1 C12 1.5515(15) . ? C2 C3 1.3460(15) . ? C4 C5 1.5225(15) . ? C4 C7 1.5278(15) . ? C4 C6 1.5289(15) . ? C8 C11 1.5261(15) . ? C8 C9 1.5296(16) . ? C8 C10 1.5304(16) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C2 108.65(9) . . ? C1 N1 C4 127.74(9) . . ? C2 N1 C4 123.38(9) . . ? C1 N2 C3 108.35(9) . . ? C1 N2 C8 127.42(9) . . ? C3 N2 C8 123.86(9) . . ? N1 C1 N2 107.89(9) . . ? N1 C1 C12 125.86(9) . . ? N2 C1 C12 126.23(9) . . ? C3 C2 N1 107.49(9) . . ? C2 C3 N2 107.62(9) . . ? N1 C4 C5 107.13(8) . . ? N1 C4 C7 108.93(9) . . ? C5 C4 C7 109.86(9) . . ? N1 C4 C6 110.38(9) . . ? C5 C4 C6 111.59(9) . . ? C7 C4 C6 108.91(9) . . ? N2 C8 C11 107.28(9) . . ? N2 C8 C9 108.64(9) . . ? C11 C8 C9 109.22(9) . . ? N2 C8 C10 110.24(9) . . ? C11 C8 C10 112.12(9) . . ? C9 C8 C10 109.27(10) . . ? O2 C12 O1 131.04(11) . . ? O2 C12 C1 114.67(10) . . ? O1 C12 C1 114.29(9) . . ? 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 C2 N1 C1 N2 -0.19(11) . . . . ? C4 N1 C1 N2 -174.74(9) . . . . ? C2 N1 C1 C12 178.52(10) . . . . ? C4 N1 C1 C12 3.97(16) . . . . ? C3 N2 C1 N1 0.27(12) . . . . ? C8 N2 C1 N1 -172.78(9) . . . . ? C3 N2 C1 C12 -178.43(10) . . . . ? C8 N2 C1 C12 8.53(17) . . . . ? C1 N1 C2 C3 0.03(12) . . . . ? C4 N1 C2 C3 174.87(9) . . . . ? N1 C2 C3 N2 0.14(12) . . . . ? C1 N2 C3 C2 -0.25(12) . . . . ? C8 N2 C3 C2 173.10(9) . . . . ? C1 N1 C4 C5 76.74(13) . . . . ? C2 N1 C4 C5 -97.08(11) . . . . ? C1 N1 C4 C7 -164.47(10) . . . . ? C2 N1 C4 C7 21.71(13) . . . . ? C1 N1 C4 C6 -44.95(14) . . . . ? C2 N1 C4 C6 141.23(10) . . . . ? C1 N2 C8 C11 69.18(13) . . . . ? C3 N2 C8 C11 -102.87(11) . . . . ? C1 N2 C8 C9 -172.87(10) . . . . ? C3 N2 C8 C9 15.08(14) . . . . ? C1 N2 C8 C10 -53.17(14) . . . . ? C3 N2 C8 C10 134.79(10) . . . . ? N1 C1 C12 O2 103.86(12) . . . . ? N2 C1 C12 O2 -77.67(14) . . . . ? N1 C1 C12 O1 -76.36(14) . . . . ? N2 C1 C12 O1 102.11(12) . . . . ? 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 C2 H2 O1 0.95 2.50 3.4496(13) 177.3 8_656 C3 H3 O1 0.95 2.43 3.2360(14) 142.9 7_576 C5 H5A O2 0.98 2.53 3.4204(14) 151.8 4_475 C7 H7A O2 0.98 2.68 3.5297(15) 145.4 4_475 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 75.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.333 _refine_diff_density_min -0.201 _refine_diff_density_rms 0.042 _iucr_refine_instructions_details ; TITL eileen42 in Pccn CELL 1.54184 13.774328 13.732915 12.825561 90.0000 90.0000 90.0000 ZERR 8.00 0.000300 0.000400 0.000300 0.0000 0.0000 0.0000 LATT 1 SYMM -x+1/2,-y+1/2, z SYMM -x, y+1/2,-z+1/2 SYMM x+1/2,-y,-z+1/2 SFAC C H N O UNIT 96.00 160.00 16.00 16.00 TEMP -173 SIZE 0.2 0.08 0.08 ACTA 150 CONF EQIV $1 0.5 -x, y, 0.5 + z EQIV $2 x, 1.5 -y, 0.5 + z EQIV $3 -0.5 + x, 2 - y, 0.5 - z HTAB C2 O1_$1 HTAB C3 O1_$2 HTAB C5 O2_$3 HTAB C7 O2_$3 MERG 2 FMAP 2 PLAN 10 L.S. 4 WGHT 0.066000 0.664700 FVAR 5.89978 N1 3 0.300537 0.900494 0.416322 11.00000 0.01919 0.02205 = 0.02159 0.00031 -0.00142 -0.00063 N2 3 0.443104 0.836850 0.445694 11.00000 0.01922 0.02292 = 0.02171 0.00040 -0.00021 -0.00085 O1 4 0.389771 0.861206 0.192681 11.00000 0.03115 0.03602 = 0.02199 -0.00195 -0.00055 0.00180 O2 4 0.474657 0.987194 0.259591 11.00000 0.02996 0.03920 = 0.03268 0.00895 -0.00051 -0.01068 C1 1 0.388889 0.884839 0.374439 11.00000 0.02047 0.02130 = 0.02253 -0.00090 -0.00098 -0.00244 C2 1 0.298922 0.861328 0.515840 11.00000 0.02279 0.02518 = 0.02135 0.00120 0.00084 -0.00156 AFIX 43 H2 2 0.245545 0.862126 0.562740 11.00000 -1.20000 AFIX 0 C3 1 0.386798 0.821935 0.533947 11.00000 0.02385 0.02575 = 0.02079 0.00205 0.00007 -0.00075 AFIX 43 H3 2 0.406667 0.789744 0.595940 11.00000 -1.20000 AFIX 0 C4 1 0.212149 0.944330 0.363894 11.00000 0.01947 0.02463 = 0.02346 0.00146 -0.00298 0.00141 C5 1 0.168812 0.865863 0.294134 11.00000 0.02289 0.02843 = 0.02782 -0.00131 -0.00426 -0.00044 AFIX 137 H5A 2 0.111982 0.892068 0.257718 11.00000 -1.50000 H5B 2 0.149199 0.810045 0.336827 11.00000 -1.50000 H5C 2 0.217358 0.844968 0.242952 11.00000 -1.50000 AFIX 0 C6 1 0.240712 1.034748 0.301479 11.00000 0.02796 0.02681 = 0.03282 0.00651 -0.00519 -0.00039 AFIX 137 H6A 2 0.280683 1.015381 0.241766 11.00000 -1.50000 H6B 2 0.277742 1.079162 0.346146 11.00000 -1.50000 H6C 2 0.182018 1.067659 0.276515 11.00000 -1.50000 AFIX 0 C7 1 0.138791 0.973629 0.447549 11.00000 0.02462 0.03417 = 0.02855 -0.00152 -0.00152 0.00655 AFIX 137 H7A 2 0.081858 1.003154 0.414376 11.00000 -1.50000 H7B 2 0.168677 1.020739 0.495128 11.00000 -1.50000 H7C 2 0.118781 0.915787 0.486803 11.00000 -1.50000 AFIX 0 C8 1 0.549892 0.812990 0.439308 11.00000 0.01735 0.02727 = 0.02772 -0.00003 -0.00103 -0.00020 C9 1 0.576406 0.747012 0.531081 11.00000 0.02231 0.03737 = 0.04009 0.01020 -0.00206 0.00341 AFIX 137 H9A 2 0.567038 0.782536 0.596583 11.00000 -1.50000 H9B 2 0.644472 0.727026 0.525025 11.00000 -1.50000 H9C 2 0.534695 0.689204 0.530432 11.00000 -1.50000 AFIX 0 C10 1 0.572288 0.760098 0.337075 11.00000 0.02217 0.03437 = 0.03624 -0.00812 0.00067 0.00185 AFIX 137 H10A 2 0.536182 0.698650 0.334673 11.00000 -1.50000 H10B 2 0.642051 0.746624 0.332967 11.00000 -1.50000 H10C 2 0.552974 0.801151 0.278117 11.00000 -1.50000 AFIX 0 C11 1 0.605415 0.908747 0.448835 11.00000 0.02263 0.03094 = 0.03186 -0.00225 -0.00202 -0.00384 AFIX 137 H11A 2 0.587561 0.951788 0.390983 11.00000 -1.50000 H11B 2 0.675341 0.895765 0.446512 11.00000 -1.50000 H11C 2 0.588995 0.940178 0.515129 11.00000 -1.50000 AFIX 0 C12 1 0.421458 0.914654 0.263125 11.00000 0.02021 0.02975 = 0.02246 0.00309 0.00120 0.00218 HKLF 4 ; _database_code_depnum_ccdc_archive 'CCDC 963623' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_eileen48 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H24 N2 O2' _chemical_formula_weight 252.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.4475(7) _cell_length_b 12.6951(7) _cell_length_c 16.1958(9) _cell_angle_alpha 90.00 _cell_angle_beta 97.919(5) _cell_angle_gamma 90.00 _cell_volume 2738.5(3) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5410 _cell_measurement_theta_min 2.6460 _cell_measurement_theta_max 27.4570 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.224 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.1419 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 56234 _diffrn_reflns_av_R_equivalents 0.0796 _diffrn_reflns_av_sigmaI/netI 0.0466 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 26.37 _reflns_number_total 5595 _reflns_number_gt 3917 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker XP' _computing_publication_material SHELXL-97 _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^)+(0.0649P)^2^+0.9779P] 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 5595 _refine_ls_number_parameters 341 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0899 _refine_ls_R_factor_gt 0.0561 _refine_ls_wR_factor_ref 0.1420 _refine_ls_wR_factor_gt 0.1257 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.29421(11) 0.48488(12) 0.11903(9) 0.0144(3) Uani 1 1 d . . . N2 N 0.45924(11) 0.48550(12) 0.14095(9) 0.0150(3) Uani 1 1 d . . . O1 O 0.35059(10) 0.71695(11) 0.18449(9) 0.0272(4) Uani 1 1 d . . . O2 O 0.40711(10) 0.70243(11) 0.06018(8) 0.0254(3) Uani 1 1 d . . . C1 C 0.37657(13) 0.54706(15) 0.13018(10) 0.0148(4) Uani 1 1 d . . . C2 C 0.32660(14) 0.37939(15) 0.12239(11) 0.0155(4) Uani 1 1 d . . . C3 C 0.42789(14) 0.38004(15) 0.13290(11) 0.0164(4) Uani 1 1 d . . . C4 C 0.18686(13) 0.52710(15) 0.10592(11) 0.0167(4) Uani 1 1 d . . . C5 C 0.11027(14) 0.44176(16) 0.07709(13) 0.0235(5) Uani 1 1 d . . . H5A H 0.1267 0.4098 0.0256 0.035 Uiso 1 1 calc R . . H5B H 0.0431 0.4730 0.0668 0.035 Uiso 1 1 calc R . . H5C H 0.1118 0.3876 0.1204 0.035 Uiso 1 1 calc R . . C6 C 0.16378(14) 0.56996(16) 0.18912(11) 0.0204(4) Uani 1 1 d . . . H6A H 0.1663 0.5124 0.2296 0.031 Uiso 1 1 calc R . . H6B H 0.0966 0.6015 0.1817 0.031 Uiso 1 1 calc R . . H6C H 0.2136 0.6236 0.2095 0.031 Uiso 1 1 calc R . . C7 C 0.17720(15) 0.61222(16) 0.03829(12) 0.0219(5) Uani 1 1 d . . . H7A H 0.2195 0.6725 0.0577 0.033 Uiso 1 1 calc R . . H7B H 0.1071 0.6350 0.0264 0.033 Uiso 1 1 calc R . . H7C H 0.1988 0.5836 -0.0125 0.033 Uiso 1 1 calc R . . C8 C 0.26233(15) 0.28264(15) 0.12244(12) 0.0204(4) Uani 1 1 d . . . H8A H 0.3052 0.2199 0.1284 0.031 Uiso 1 1 calc R . . H8B H 0.2167 0.2787 0.0699 0.031 Uiso 1 1 calc R . . H8C H 0.2232 0.2862 0.1691 0.031 Uiso 1 1 calc R . . C9 C 0.49524(14) 0.28737(16) 0.12575(12) 0.0209(4) Uani 1 1 d . . . H9A H 0.4548 0.2266 0.1043 0.031 Uiso 1 1 calc R . . H9B H 0.5317 0.2704 0.1808 0.031 Uiso 1 1 calc R . . H9C H 0.5433 0.3045 0.0875 0.031 Uiso 1 1 calc R . . C10 C 0.56712(14) 0.52319(16) 0.16044(12) 0.0186(4) Uani 1 1 d . . . C11 C 0.57231(15) 0.62457(16) 0.21165(12) 0.0235(5) Uani 1 1 d . . . H11A H 0.5383 0.6814 0.1778 0.035 Uiso 1 1 calc R . . H11B H 0.6427 0.6438 0.2287 0.035 Uiso 1 1 calc R . . H11C H 0.5393 0.6136 0.2613 0.035 Uiso 1 1 calc R . . C12 C 0.62928(15) 0.44231(18) 0.21592(14) 0.0304(5) Uani 1 1 d . . . H12A H 0.5895 0.4151 0.2576 0.046 Uiso 1 1 calc R . . H12B H 0.6902 0.4761 0.2442 0.046 Uiso 1 1 calc R . . H12C H 0.6479 0.3840 0.1815 0.046 Uiso 1 1 calc R . . C13 C 0.60929(15) 0.53989(17) 0.07892(12) 0.0260(5) Uani 1 1 d . . . H13A H 0.6071 0.4733 0.0481 0.039 Uiso 1 1 calc R . . H13B H 0.6789 0.5643 0.0908 0.039 Uiso 1 1 calc R . . H13C H 0.5690 0.5929 0.0453 0.039 Uiso 1 1 calc R . . C14 C 0.37804(14) 0.66918(16) 0.12487(12) 0.0193(4) Uani 1 1 d . . . N1' N 0.04918(11) 0.48720(12) 0.36976(9) 0.0161(4) Uani 1 1 d . . . N2' N 0.21340(11) 0.48180(12) 0.39690(9) 0.0158(4) Uani 1 1 d . . . O1' O 0.13173(11) 0.27458(12) 0.29408(9) 0.0307(4) Uani 1 1 d . . . O2' O 0.11850(11) 0.24939(12) 0.43018(9) 0.0335(4) Uani 1 1 d . . . C1' C 0.12987(13) 0.42295(15) 0.37933(11) 0.0163(4) Uani 1 1 d . . . C2' C 0.08360(14) 0.59160(15) 0.38011(11) 0.0176(4) Uani 1 1 d . . . C3' C 0.18446(14) 0.58837(15) 0.39647(11) 0.0180(4) Uani 1 1 d . . . C4' C -0.05934(14) 0.45589(16) 0.33922(12) 0.0194(4) Uani 1 1 d . . . C5' C -0.07927(17) 0.33987(19) 0.35184(17) 0.0400(6) Uani 1 1 d . . . H5'1 H -0.0391 0.2978 0.3180 0.060 Uiso 1 1 calc R . . H5'2 H -0.1507 0.3250 0.3349 0.060 Uiso 1 1 calc R . . H5'3 H -0.0609 0.3218 0.4108 0.060 Uiso 1 1 calc R . . C6' C -0.07885(15) 0.4807(2) 0.24571(12) 0.0310(5) Uani 1 1 d . . . H6'1 H -0.0306 0.4423 0.2169 0.046 Uiso 1 1 calc R . . H6'2 H -0.0713 0.5566 0.2372 0.046 Uiso 1 1 calc R . . H6'3 H -0.1472 0.4592 0.2232 0.046 Uiso 1 1 calc R . . C7' C -0.12994(15) 0.51728(19) 0.38812(14) 0.0311(5) Uani 1 1 d . . . H7'1 H -0.1964 0.4841 0.3803 0.047 Uiso 1 1 calc R . . H7'2 H -0.1357 0.5901 0.3679 0.047 Uiso 1 1 calc R . . H7'3 H -0.1030 0.5169 0.4475 0.047 Uiso 1 1 calc R . . C8' C 0.01981(16) 0.68899(16) 0.37288(13) 0.0266(5) Uani 1 1 d . . . H8'1 H -0.0163 0.6941 0.4213 0.040 Uiso 1 1 calc R . . H8'2 H -0.0286 0.6854 0.3218 0.040 Uiso 1 1 calc R . . H8'3 H 0.0626 0.7511 0.3708 0.040 Uiso 1 1 calc R . . C9' C 0.25349(16) 0.68169(17) 0.40563(14) 0.0293(5) Uani 1 1 d . . . H9'1 H 0.2909 0.6850 0.3578 0.044 Uiso 1 1 calc R . . H9'2 H 0.3007 0.6748 0.4571 0.044 Uiso 1 1 calc R . . H9'3 H 0.2140 0.7463 0.4079 0.044 Uiso 1 1 calc R . . C10' C 0.32169(14) 0.44400(16) 0.41639(11) 0.0197(4) Uani 1 1 d . . . C11' C 0.33191(16) 0.32497(17) 0.41379(15) 0.0336(6) Uani 1 1 d . . . H11D H 0.2941 0.2932 0.4550 0.050 Uiso 1 1 calc R . . H11E H 0.4029 0.3056 0.4266 0.050 Uiso 1 1 calc R . . H11F H 0.3053 0.2993 0.3580 0.050 Uiso 1 1 calc R . . C12' C 0.38214(16) 0.4890(2) 0.35094(14) 0.0358(6) Uani 1 1 d . . . H12D H 0.4510 0.4621 0.3611 0.054 Uiso 1 1 calc R . . H12E H 0.3831 0.5661 0.3547 0.054 Uiso 1 1 calc R . . H12F H 0.3509 0.4677 0.2952 0.054 Uiso 1 1 calc R . . C13' C 0.36193(16) 0.47885(19) 0.50497(12) 0.0294(5) Uani 1 1 d . . . H13D H 0.3168 0.4540 0.5434 0.044 Uiso 1 1 calc R . . H13E H 0.3658 0.5559 0.5072 0.044 Uiso 1 1 calc R . . H13F H 0.4290 0.4490 0.5211 0.044 Uiso 1 1 calc R . . C14' C 0.12639(14) 0.30159(16) 0.36700(12) 0.0215(4) 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 N1 0.0147(8) 0.0150(9) 0.0134(8) 0.0002(6) 0.0016(6) -0.0004(7) N2 0.0156(8) 0.0153(9) 0.0144(8) -0.0006(6) 0.0028(6) -0.0005(7) O1 0.0273(8) 0.0218(8) 0.0329(8) -0.0096(6) 0.0056(6) -0.0002(6) O2 0.0271(8) 0.0219(8) 0.0269(8) 0.0068(6) 0.0031(6) -0.0020(6) C1 0.0171(10) 0.0167(10) 0.0105(9) -0.0008(7) 0.0017(7) 0.0004(8) C2 0.0200(10) 0.0132(10) 0.0130(9) -0.0004(7) 0.0019(7) 0.0005(8) C3 0.0211(11) 0.0139(10) 0.0140(9) 0.0010(7) 0.0022(7) -0.0001(8) C4 0.0139(10) 0.0178(10) 0.0180(9) 0.0000(8) 0.0009(7) 0.0023(8) C5 0.0180(10) 0.0214(11) 0.0297(11) -0.0017(9) -0.0018(8) 0.0016(9) C6 0.0206(10) 0.0207(11) 0.0205(10) 0.0006(8) 0.0044(8) 0.0026(9) C7 0.0206(11) 0.0250(12) 0.0197(10) 0.0041(8) 0.0012(8) 0.0033(9) C8 0.0217(11) 0.0172(11) 0.0214(10) 0.0011(8) 0.0005(8) -0.0006(8) C9 0.0221(11) 0.0165(11) 0.0244(10) 0.0011(8) 0.0040(8) 0.0022(8) C10 0.0131(10) 0.0205(11) 0.0221(10) -0.0007(8) 0.0022(8) -0.0010(8) C11 0.0229(11) 0.0258(12) 0.0214(10) -0.0050(9) 0.0022(8) -0.0072(9) C12 0.0202(11) 0.0298(13) 0.0382(13) 0.0040(10) -0.0069(9) -0.0013(10) C13 0.0224(11) 0.0311(13) 0.0259(11) -0.0043(9) 0.0078(9) -0.0078(9) C14 0.0163(10) 0.0168(11) 0.0239(10) -0.0009(8) -0.0003(8) -0.0005(8) N1' 0.0152(8) 0.0165(9) 0.0165(8) 0.0000(6) 0.0024(6) 0.0002(7) N2' 0.0143(8) 0.0162(9) 0.0166(8) -0.0017(6) 0.0012(6) 0.0005(7) O1' 0.0356(9) 0.0259(9) 0.0294(8) -0.0104(7) 0.0003(7) 0.0003(7) O2' 0.0367(9) 0.0260(9) 0.0363(9) 0.0131(7) -0.0009(7) -0.0035(7) C1' 0.0178(10) 0.0189(11) 0.0124(9) 0.0009(8) 0.0028(7) 0.0002(8) C2' 0.0222(11) 0.0156(10) 0.0154(9) -0.0003(8) 0.0037(8) 0.0009(8) C3' 0.0212(11) 0.0178(11) 0.0154(9) -0.0030(8) 0.0040(8) -0.0018(8) C4' 0.0121(10) 0.0225(11) 0.0235(10) 0.0009(8) 0.0022(8) -0.0021(8) C5' 0.0221(12) 0.0300(14) 0.0665(17) 0.0090(12) 0.0014(11) -0.0077(10) C6' 0.0211(11) 0.0494(15) 0.0221(11) -0.0025(10) 0.0017(9) -0.0047(10) C7' 0.0176(11) 0.0446(15) 0.0324(12) -0.0069(10) 0.0080(9) 0.0002(10) C8' 0.0291(12) 0.0177(11) 0.0320(12) -0.0027(9) 0.0007(9) 0.0049(9) C9' 0.0251(12) 0.0224(12) 0.0401(13) -0.0104(10) 0.0033(10) -0.0039(9) C10' 0.0143(10) 0.0269(12) 0.0178(10) -0.0005(8) 0.0018(8) 0.0020(9) C11' 0.0236(12) 0.0262(13) 0.0486(14) -0.0069(11) -0.0030(10) 0.0093(10) C12' 0.0206(12) 0.0572(17) 0.0312(12) 0.0145(11) 0.0095(9) 0.0088(11) C13' 0.0253(12) 0.0380(14) 0.0231(11) -0.0039(10) -0.0039(9) 0.0042(10) C14' 0.0173(11) 0.0179(11) 0.0280(11) 0.0015(9) -0.0016(8) -0.0001(8) _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 C1 1.352(2) . ? N1 C2 1.407(2) . ? N1 C4 1.527(2) . ? N2 C1 1.350(2) . ? N2 C3 1.404(2) . ? N2 C10 1.519(2) . ? O1 C14 1.239(2) . ? O2 C14 1.242(2) . ? C1 C14 1.553(3) . ? C2 C3 1.349(3) . ? C2 C8 1.502(3) . ? C3 C9 1.499(3) . ? C4 C5 1.523(3) . ? C4 C6 1.524(3) . ? C4 C7 1.531(3) . ? C10 C13 1.522(3) . ? C10 C11 1.527(3) . ? C10 C12 1.534(3) . ? N1' C1' 1.349(2) . ? N1' C2' 1.406(2) . ? N1' C4' 1.528(2) . ? N2' C1' 1.346(2) . ? N2' C3' 1.408(2) . ? N2' C10' 1.524(2) . ? O1' C14' 1.241(2) . ? O2' C14' 1.236(2) . ? C1' C14' 1.553(3) . ? C2' C3' 1.346(3) . ? C2' C8' 1.500(3) . ? C3' C9' 1.500(3) . ? C4' C5' 1.516(3) . ? C4' C7' 1.531(3) . ? C4' C6' 1.534(3) . ? C10' C11' 1.518(3) . ? C10' C13' 1.527(3) . ? C10' C12' 1.532(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 C1 N1 C2 107.88(15) . . ? C1 N1 C4 123.72(15) . . ? C2 N1 C4 128.40(15) . . ? C1 N2 C3 107.97(15) . . ? C1 N2 C10 126.18(16) . . ? C3 N2 C10 125.84(15) . . ? N2 C1 N1 108.91(16) . . ? N2 C1 C14 124.64(16) . . ? N1 C1 C14 126.30(16) . . ? C3 C2 N1 107.50(16) . . ? C3 C2 C8 125.17(17) . . ? N1 C2 C8 127.10(16) . . ? C2 C3 N2 107.61(16) . . ? C2 C3 C9 126.56(18) . . ? N2 C3 C9 125.35(17) . . ? C5 C4 C6 108.26(15) . . ? C5 C4 N1 112.29(15) . . ? C6 C4 N1 107.83(14) . . ? C5 C4 C7 107.19(15) . . ? C6 C4 C7 111.90(16) . . ? N1 C4 C7 109.42(14) . . ? N2 C10 C13 108.84(15) . . ? N2 C10 C11 110.44(15) . . ? C13 C10 C11 111.04(16) . . ? N2 C10 C12 109.80(16) . . ? C13 C10 C12 111.30(17) . . ? C11 C10 C12 105.39(17) . . ? O1 C14 O2 130.81(19) . . ? O1 C14 C1 115.99(17) . . ? O2 C14 C1 113.21(16) . . ? C1' N1' C2' 108.04(15) . . ? C1' N1' C4' 126.67(16) . . ? C2' N1' C4' 124.60(15) . . ? C1' N2' C3' 108.07(15) . . ? C1' N2' C10' 127.91(16) . . ? C3' N2' C10' 124.00(15) . . ? N2' C1' N1' 108.86(16) . . ? N2' C1' C14' 125.94(16) . . ? N1' C1' C14' 125.12(16) . . ? C3' C2' N1' 107.51(17) . . ? C3' C2' C8' 126.17(18) . . ? N1' C2' C8' 126.31(17) . . ? C2' C3' N2' 107.50(16) . . ? C2' C3' C9' 126.04(18) . . ? N2' C3' C9' 126.29(17) . . ? C5' C4' N1' 112.82(16) . . ? C5' C4' C7' 106.93(17) . . ? N1' C4' C7' 109.45(16) . . ? C5' C4' C6' 108.88(18) . . ? N1' C4' C6' 106.98(15) . . ? C7' C4' C6' 111.86(17) . . ? C11' C10' N2' 113.28(16) . . ? C11' C10' C13' 107.01(17) . . ? N2' C10' C13' 107.94(15) . . ? C11' C10' C12' 107.05(18) . . ? N2' C10' C12' 108.79(15) . . ? C13' C10' C12' 112.86(18) . . ? O2' C14' O1' 131.5(2) . . ? O2' C14' C1' 115.46(18) . . ? O1' C14' C1' 113.05(17) . . ? 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 C3 N2 C1 N1 2.44(18) . . . . ? C10 N2 C1 N1 -176.18(15) . . . . ? C3 N2 C1 C14 -173.24(16) . . . . ? C10 N2 C1 C14 8.1(3) . . . . ? C2 N1 C1 N2 -0.40(18) . . . . ? C4 N1 C1 N2 179.27(14) . . . . ? C2 N1 C1 C14 175.20(16) . . . . ? C4 N1 C1 C14 -5.1(3) . . . . ? C1 N1 C2 C3 -1.88(19) . . . . ? C4 N1 C2 C3 178.47(15) . . . . ? C1 N1 C2 C8 172.90(17) . . . . ? C4 N1 C2 C8 -6.7(3) . . . . ? N1 C2 C3 N2 3.32(19) . . . . ? C8 C2 C3 N2 -171.58(16) . . . . ? N1 C2 C3 C9 -169.03(16) . . . . ? C8 C2 C3 C9 16.1(3) . . . . ? C1 N2 C3 C2 -3.62(19) . . . . ? C10 N2 C3 C2 175.02(15) . . . . ? C1 N2 C3 C9 168.86(17) . . . . ? C10 N2 C3 C9 -12.5(3) . . . . ? C1 N1 C4 C5 167.97(16) . . . . ? C2 N1 C4 C5 -12.4(2) . . . . ? C1 N1 C4 C6 -72.8(2) . . . . ? C2 N1 C4 C6 106.75(19) . . . . ? C1 N1 C4 C7 49.1(2) . . . . ? C2 N1 C4 C7 -131.32(18) . . . . ? C1 N2 C10 C13 -91.1(2) . . . . ? C3 N2 C10 C13 90.5(2) . . . . ? C1 N2 C10 C11 31.0(2) . . . . ? C3 N2 C10 C11 -147.40(17) . . . . ? C1 N2 C10 C12 146.79(18) . . . . ? C3 N2 C10 C12 -31.6(2) . . . . ? N2 C1 C14 O1 -110.8(2) . . . . ? N1 C1 C14 O1 74.3(2) . . . . ? N2 C1 C14 O2 69.3(2) . . . . ? N1 C1 C14 O2 -105.7(2) . . . . ? C3' N2' C1' N1' -1.45(19) . . . . ? C10' N2' C1' N1' 177.17(15) . . . . ? C3' N2' C1' C14' 175.37(16) . . . . ? C10' N2' C1' C14' -6.0(3) . . . . ? C2' N1' C1' N2' 1.24(19) . . . . ? C4' N1' C1' N2' 172.09(15) . . . . ? C2' N1' C1' C14' -175.62(16) . . . . ? C4' N1' C1' C14' -4.8(3) . . . . ? C1' N1' C2' C3' -0.5(2) . . . . ? C4' N1' C2' C3' -171.62(15) . . . . ? C1' N1' C2' C8' 178.56(18) . . . . ? C4' N1' C2' C8' 7.5(3) . . . . ? N1' C2' C3' N2' -0.3(2) . . . . ? C8' C2' C3' N2' -179.44(17) . . . . ? N1' C2' C3' C9' 175.15(17) . . . . ? C8' C2' C3' C9' -4.0(3) . . . . ? C1' N2' C3' C2' 1.1(2) . . . . ? C10' N2' C3' C2' -177.58(15) . . . . ? C1' N2' C3' C9' -174.37(18) . . . . ? C10' N2' C3' C9' 6.9(3) . . . . ? C1' N1' C4' C5' 23.1(3) . . . . ? C2' N1' C4' C5' -167.53(18) . . . . ? C1' N1' C4' C7' 141.98(18) . . . . ? C2' N1' C4' C7' -48.6(2) . . . . ? C1' N1' C4' C6' -96.6(2) . . . . ? C2' N1' C4' C6' 72.8(2) . . . . ? C1' N2' C10' C11' 0.7(3) . . . . ? C3' N2' C10' C11' 179.16(17) . . . . ? C1' N2' C10' C13' -117.6(2) . . . . ? C3' N2' C10' C13' 60.9(2) . . . . ? C1' N2' C10' C12' 119.6(2) . . . . ? C3' N2' C10' C12' -61.9(2) . . . . ? N2' C1' C14' O2' 92.7(2) . . . . ? N1' C1' C14' O2' -91.0(2) . . . . ? N2' C1' C14' O1' -87.6(2) . . . . ? N1' C1' C14' O1' 88.7(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 C9 H9B O1 0.98 2.60 3.576(2) 171.7 2_645 C9 H9C O2 0.98 2.57 3.449(2) 149.2 3_665 C9' H9'2 O2 0.98 2.57 3.357(2) 137.4 4_576 C8' H8'2 O1' 0.98 2.45 3.336(3) 149.8 2 C8 H8C O1' 0.98 2.51 3.488(2) 173.2 . C8 H8B O2' 0.98 2.48 3.456(2) 171.8 4_565 C5 H5A O2' 0.98 2.54 3.411(2) 148.5 4_565 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.382 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.051 _iucr_refine_instructions_details ; TITL eileen48 in P2(1)/c CELL 0.71073 13.447512 12.695079 16.195829 90.0000 97.9192 90.0000 ZERR 8.00 0.000700 0.000700 0.000900 0.0000 0.0050 0.0000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H N O UNIT 112 192 16 16 MERG 2 TEMP -173 FMAP 2 PLAN 10 SHEL 999 0.8 ACTA CONF EQIV $1 -x+1, -0.5+y, 0.5-z EQIV $2 -x+1, -y+1, -z EQIV $3 x, 1.5-y, 0.5+z EQIV $4 -x, 0.5+y, 0.5-z EQIV $5 x, 0.5-y, -0.5+z HTAB C9 O1_$1 HTAB C9 O2_$2 HTAB C9' O2_$3 HTAB C8' O1'_$4 HTAB C8 O1' HTAB C8 O2'_$5 HTAB C5 O2'_$5 L.S. 4 WGHT 0.064900 0.977900 FVAR 2.43615 N1 3 0.294212 0.484883 0.119030 11.00000 0.01472 0.01495 = 0.01335 0.00024 0.00164 -0.00037 N2 3 0.459236 0.485503 0.140947 11.00000 0.01561 0.01534 = 0.01437 -0.00058 0.00281 -0.00049 O1 4 0.350591 0.716954 0.184488 11.00000 0.02732 0.02183 = 0.03286 -0.00960 0.00562 -0.00018 O2 4 0.407110 0.702432 0.060182 11.00000 0.02711 0.02193 = 0.02692 0.00683 0.00308 -0.00200 C1 1 0.376571 0.547061 0.130183 11.00000 0.01706 0.01666 = 0.01050 -0.00076 0.00171 0.00039 C2 1 0.326603 0.379387 0.122389 11.00000 0.02005 0.01318 = 0.01301 -0.00043 0.00189 0.00052 C3 1 0.427889 0.380041 0.132900 11.00000 0.02113 0.01392 = 0.01401 0.00101 0.00217 -0.00006 C4 1 0.186860 0.527100 0.105921 11.00000 0.01390 0.01777 = 0.01796 -0.00002 0.00087 0.00231 C5 1 0.110266 0.441756 0.077094 11.00000 0.01801 0.02143 = 0.02966 -0.00166 -0.00180 0.00164 AFIX 137 H5A 2 0.126710 0.409761 0.025594 11.00000 -1.50000 H5B 2 0.043056 0.472988 0.066764 11.00000 -1.50000 H5C 2 0.111754 0.387613 0.120377 11.00000 -1.50000 AFIX 0 C6 1 0.163775 0.569955 0.189125 11.00000 0.02058 0.02072 = 0.02047 0.00061 0.00435 0.00262 AFIX 137 H6A 2 0.166291 0.512361 0.229649 11.00000 -1.50000 H6B 2 0.096612 0.601477 0.181671 11.00000 -1.50000 H6C 2 0.213582 0.623581 0.209546 11.00000 -1.50000 AFIX 0 C7 1 0.177199 0.612217 0.038288 11.00000 0.02065 0.02496 = 0.01971 0.00414 0.00115 0.00327 AFIX 137 H7A 2 0.219542 0.672540 0.057727 11.00000 -1.50000 H7B 2 0.107058 0.635005 0.026399 11.00000 -1.50000 H7C 2 0.198816 0.583576 -0.012543 11.00000 -1.50000 AFIX 0 C8 1 0.262330 0.282642 0.122444 11.00000 0.02173 0.01722 = 0.02144 0.00114 0.00051 -0.00063 AFIX 137 H8A 2 0.305225 0.219937 0.128388 11.00000 -1.50000 H8B 2 0.216672 0.278665 0.069874 11.00000 -1.50000 H8C 2 0.223156 0.286198 0.169107 11.00000 -1.50000 AFIX 0 C9 1 0.495243 0.287371 0.125745 11.00000 0.02208 0.01645 = 0.02441 0.00109 0.00396 0.00216 AFIX 137 H9A 2 0.454760 0.226587 0.104295 11.00000 -1.50000 H9B 2 0.531658 0.270441 0.180788 11.00000 -1.50000 H9C 2 0.543349 0.304496 0.087475 11.00000 -1.50000 AFIX 0 C10 1 0.567122 0.523189 0.160444 11.00000 0.01306 0.02050 = 0.02208 -0.00071 0.00224 -0.00102 C11 1 0.572315 0.624569 0.211648 11.00000 0.02290 0.02581 = 0.02144 -0.00505 0.00218 -0.00723 AFIX 137 H11A 2 0.538265 0.681351 0.177816 11.00000 -1.50000 H11B 2 0.642721 0.643805 0.228727 11.00000 -1.50000 H11C 2 0.539290 0.613596 0.261254 11.00000 -1.50000 AFIX 0 C12 1 0.629284 0.442314 0.215924 11.00000 0.02016 0.02977 = 0.03822 0.00401 -0.00686 -0.00134 AFIX 137 H12A 2 0.589450 0.415137 0.257568 11.00000 -1.50000 H12B 2 0.690162 0.476101 0.244182 11.00000 -1.50000 H12C 2 0.647949 0.384038 0.181465 11.00000 -1.50000 AFIX 0 C13 1 0.609292 0.539895 0.078924 11.00000 0.02238 0.03109 = 0.02590 -0.00433 0.00782 -0.00776 AFIX 137 H13A 2 0.607108 0.473326 0.048089 11.00000 -1.50000 H13B 2 0.678941 0.564264 0.090844 11.00000 -1.50000 H13C 2 0.568981 0.592852 0.045342 11.00000 -1.50000 AFIX 0 C14 1 0.378039 0.669178 0.124869 11.00000 0.01630 0.01683 = 0.02386 -0.00093 -0.00027 -0.00050 N1' 3 0.049176 0.487197 0.369758 11.00000 0.01524 0.01653 = 0.01653 0.00003 0.00241 0.00021 N2' 3 0.213403 0.481797 0.396902 11.00000 0.01430 0.01620 = 0.01656 -0.00172 0.00121 0.00052 O1' 4 0.131725 0.274575 0.294083 11.00000 0.03562 0.02588 = 0.02936 -0.01038 0.00031 0.00028 O2' 4 0.118503 0.249393 0.430180 11.00000 0.03666 0.02604 = 0.03627 0.01307 -0.00091 -0.00346 C1' 1 0.129867 0.422948 0.379327 11.00000 0.01781 0.01893 = 0.01237 0.00092 0.00285 0.00021 C2' 1 0.083603 0.591597 0.380106 11.00000 0.02223 0.01558 = 0.01543 -0.00028 0.00372 0.00088 C3' 1 0.184463 0.588365 0.396471 11.00000 0.02123 0.01784 = 0.01536 -0.00299 0.00398 -0.00179 C4' 1 -0.059344 0.455894 0.339222 11.00000 0.01213 0.02252 = 0.02348 0.00091 0.00221 -0.00208 C5' 1 -0.079266 0.339869 0.351840 11.00000 0.02207 0.02996 = 0.06653 0.00903 0.00140 -0.00769 AFIX 137 H5'1 2 -0.039056 0.297752 0.317995 11.00000 -1.50000 H5'2 2 -0.150679 0.325046 0.334877 11.00000 -1.50000 H5'3 2 -0.060944 0.321806 0.410803 11.00000 -1.50000 AFIX 0 C6' 1 -0.078850 0.480740 0.245710 11.00000 0.02109 0.04939 = 0.02208 -0.00248 0.00172 -0.00474 AFIX 137 H6'1 2 -0.030555 0.442349 0.216907 11.00000 -1.50000 H6'2 2 -0.071251 0.556593 0.237240 11.00000 -1.50000 H6'3 2 -0.147208 0.459155 0.223233 11.00000 -1.50000 AFIX 0 C7' 1 -0.129937 0.517283 0.388123 11.00000 0.01763 0.04459 = 0.03241 -0.00685 0.00798 0.00018 AFIX 137 H7'1 2 -0.196378 0.484118 0.380259 11.00000 -1.50000 H7'2 2 -0.135678 0.590089 0.367915 11.00000 -1.50000 H7'3 2 -0.102953 0.516945 0.447502 11.00000 -1.50000 AFIX 0 C8' 1 0.019808 0.688987 0.372877 11.00000 0.02906 0.01768 = 0.03198 -0.00268 0.00072 0.00490 AFIX 137 H8'1 2 -0.016328 0.694093 0.421301 11.00000 -1.50000 H8'2 2 -0.028570 0.685380 0.321840 11.00000 -1.50000 H8'3 2 0.062648 0.751108 0.370769 11.00000 -1.50000 AFIX 0 C9' 1 0.253488 0.681689 0.405626 11.00000 0.02508 0.02237 = 0.04005 -0.01038 0.00334 -0.00394 AFIX 137 H9'1 2 0.290869 0.684972 0.357848 11.00000 -1.50000 H9'2 2 0.300689 0.674822 0.457130 11.00000 -1.50000 H9'3 2 0.214008 0.746255 0.407883 11.00000 -1.50000 AFIX 0 C10' 1 0.321686 0.443997 0.416388 11.00000 0.01432 0.02692 = 0.01776 -0.00052 0.00178 0.00199 C11' 1 0.331915 0.324971 0.413790 11.00000 0.02356 0.02623 = 0.04863 -0.00692 -0.00305 0.00928 AFIX 137 H11D 2 0.294147 0.293193 0.455035 11.00000 -1.50000 H11E 2 0.402905 0.305587 0.426616 11.00000 -1.50000 H11F 2 0.305295 0.299311 0.358042 11.00000 -1.50000 AFIX 0 C12' 1 0.382135 0.489012 0.350943 11.00000 0.02060 0.05724 = 0.03116 0.01451 0.00955 0.00883 AFIX 137 H12D 2 0.451038 0.462089 0.361091 11.00000 -1.50000 H12E 2 0.383119 0.566061 0.354688 11.00000 -1.50000 H12F 2 0.350907 0.467673 0.295197 11.00000 -1.50000 AFIX 0 C13' 1 0.361935 0.478847 0.504966 11.00000 0.02528 0.03799 = 0.02305 -0.00389 -0.00385 0.00422 AFIX 137 H13D 2 0.316804 0.453961 0.543430 11.00000 -1.50000 H13E 2 0.365814 0.555903 0.507155 11.00000 -1.50000 H13F 2 0.429013 0.449038 0.521148 11.00000 -1.50000 AFIX 0 C14' 1 0.126388 0.301592 0.367004 11.00000 0.01731 0.01786 = 0.02799 0.00148 -0.00158 -0.00006 HKLF 4 ; _database_code_depnum_ccdc_archive 'CCDC 963624' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_eileen36 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H20 B F15 N4 O' _chemical_formula_weight 736.30 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' B B 0.0013 0.0007 '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 orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' 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 12.5421(2) _cell_length_b 12.7742(2) _cell_length_c 18.7596(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3005.57(9) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 21362 _cell_measurement_theta_min 2.1669 _cell_measurement_theta_max 29.3084 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.627 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1480 _exptl_absorpt_coefficient_mu 0.164 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.98890 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; ? ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.1419 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 124268 _diffrn_reflns_av_R_equivalents 0.0548 _diffrn_reflns_av_sigmaI/netI 0.0182 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 27.87 _reflns_number_total 4000 _reflns_number_gt 3568 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; ? ; _computing_cell_refinement ; ? ; _computing_data_reduction ; ? ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'BRUKER XP' _computing_publication_material SHELXL-97 _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. In the absence of significant anomalous dispersion, Friedel opposite reflections were merged; the Flack parameter is thus meaningless. ; _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^)+(0.0266P)^2^+0.9437P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.2(4) _chemical_absolute_configuration . _refine_ls_number_reflns 4000 _refine_ls_number_parameters 457 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0376 _refine_ls_R_factor_gt 0.0297 _refine_ls_wR_factor_ref 0.0643 _refine_ls_wR_factor_gt 0.0612 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _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 B B 0.35946(17) 0.40022(16) 0.54473(12) 0.0176(4) Uani 1 1 d . . . N1 N 0.57313(14) 0.72053(13) 0.68132(9) 0.0204(3) Uani 1 1 d . . . N2 N 0.40666(14) 0.72905(12) 0.71670(9) 0.0204(3) Uani 1 1 d . . . N3 N 0.47531(14) 0.55707(12) 0.67751(9) 0.0207(4) Uani 1 1 d . . . N4 N 0.42556(13) 0.53718(12) 0.62130(9) 0.0191(3) Uani 1 1 d . . . O O 0.42359(11) 0.43433(10) 0.61043(7) 0.0182(3) Uani 1 1 d . . . F1 F 0.38511(10) 0.61522(9) 0.48725(6) 0.0243(3) Uani 1 1 d . . . F2 F 0.51078(11) 0.67447(11) 0.38124(8) 0.0379(3) Uani 1 1 d . . . F3 F 0.62006(11) 0.52991(13) 0.30290(7) 0.0426(4) Uani 1 1 d . . . F4 F 0.60086(12) 0.32344(13) 0.33520(8) 0.0480(4) Uani 1 1 d . . . F5 F 0.48390(12) 0.26109(10) 0.44328(8) 0.0418(4) Uani 1 1 d . . . F6 F 0.48118(12) 0.24510(9) 0.64078(7) 0.0370(3) Uani 1 1 d . . . F7 F 0.43517(12) 0.04605(9) 0.65612(7) 0.0382(3) Uani 1 1 d . . . F8 F 0.28511(11) -0.04825(9) 0.57177(8) 0.0373(3) Uani 1 1 d . . . F9 F 0.18057(11) 0.06929(10) 0.47143(8) 0.0405(4) Uani 1 1 d . . . F10 F 0.21949(11) 0.27320(10) 0.45971(7) 0.0333(3) Uani 1 1 d . . . F11 F 0.21697(9) 0.50954(10) 0.43298(6) 0.0253(3) Uani 1 1 d . . . F12 F 0.02191(10) 0.57973(11) 0.45619(7) 0.0366(3) Uani 1 1 d . . . F13 F -0.07558(11) 0.54903(14) 0.58331(9) 0.0520(4) Uani 1 1 d . . . F14 F 0.03175(12) 0.44903(14) 0.69052(7) 0.0512(4) Uani 1 1 d . . . F15 F 0.23116(11) 0.38357(10) 0.67056(6) 0.0314(3) Uani 1 1 d . . . C1 C 0.48207(16) 0.66628(15) 0.68979(10) 0.0182(4) Uani 1 1 d . . . C2 C 0.55230(19) 0.82277(16) 0.70148(11) 0.0267(5) Uani 1 1 d . . . H2 H 0.6015 0.8793 0.7001 0.032 Uiso 1 1 calc R . . C3 C 0.45129(19) 0.82800(16) 0.72311(11) 0.0273(5) Uani 1 1 d . . . H3 H 0.4159 0.8889 0.7400 0.033 Uiso 1 1 calc R . . C4 C 0.67708(17) 0.68222(16) 0.65000(11) 0.0242(4) Uani 1 1 d . . . C5 C 0.70659(19) 0.57693(18) 0.68327(13) 0.0327(5) Uani 1 1 d . . . H5A H 0.7034 0.5825 0.7353 0.049 Uiso 1 1 calc R . . H5B H 0.7790 0.5576 0.6688 0.049 Uiso 1 1 calc R . . H5C H 0.6563 0.5232 0.6670 0.049 Uiso 1 1 calc R . . C6 C 0.6631(2) 0.67485(18) 0.56953(11) 0.0303(5) Uani 1 1 d . . . H6A H 0.6070 0.6240 0.5585 0.045 Uiso 1 1 calc R . . H6B H 0.7303 0.6522 0.5477 0.045 Uiso 1 1 calc R . . H6C H 0.6431 0.7436 0.5506 0.045 Uiso 1 1 calc R . . C7 C 0.7640(2) 0.7614(2) 0.66810(13) 0.0368(6) Uani 1 1 d . . . H7A H 0.7457 0.8295 0.6475 0.055 Uiso 1 1 calc R . . H7B H 0.8322 0.7374 0.6484 0.055 Uiso 1 1 calc R . . H7C H 0.7700 0.7680 0.7200 0.055 Uiso 1 1 calc R . . C8 C 0.29270(18) 0.70263(16) 0.73661(12) 0.0253(4) Uani 1 1 d . . . C9 C 0.22767(18) 0.70139(17) 0.66767(12) 0.0292(5) Uani 1 1 d . . . H9A H 0.2321 0.7701 0.6446 0.044 Uiso 1 1 calc R . . H9B H 0.1530 0.6855 0.6787 0.044 Uiso 1 1 calc R . . H9C H 0.2562 0.6478 0.6355 0.044 Uiso 1 1 calc R . . C10 C 0.29012(19) 0.59748(18) 0.77576(13) 0.0316(5) Uani 1 1 d . . . H10A H 0.3083 0.5411 0.7425 0.047 Uiso 1 1 calc R . . H10B H 0.2185 0.5855 0.7950 0.047 Uiso 1 1 calc R . . H10C H 0.3419 0.5985 0.8149 0.047 Uiso 1 1 calc R . . C11 C 0.2514(2) 0.78766(19) 0.78671(13) 0.0354(6) Uani 1 1 d . . . H11A H 0.2994 0.7940 0.8277 0.053 Uiso 1 1 calc R . . H11B H 0.1798 0.7689 0.8033 0.053 Uiso 1 1 calc R . . H11C H 0.2484 0.8546 0.7612 0.053 Uiso 1 1 calc R . . C12 C 0.42641(15) 0.43425(16) 0.47285(10) 0.0198(4) Uani 1 1 d . . . C13 C 0.43820(15) 0.53905(16) 0.45231(11) 0.0207(4) Uani 1 1 d . . . C14 C 0.50174(17) 0.57196(18) 0.39654(12) 0.0272(5) Uani 1 1 d . . . C15 C 0.55669(16) 0.4996(2) 0.35664(11) 0.0300(5) Uani 1 1 d . . . C16 C 0.54713(18) 0.3953(2) 0.37328(12) 0.0318(5) Uani 1 1 d . . . C17 C 0.48435(17) 0.36538(17) 0.43042(12) 0.0261(4) Uani 1 1 d . . . C18 C 0.34762(15) 0.27272(15) 0.55245(10) 0.0183(4) Uani 1 1 d . . . C19 C 0.40176(17) 0.20812(16) 0.59933(11) 0.0226(4) Uani 1 1 d . . . C20 C 0.38105(18) 0.10206(16) 0.60708(11) 0.0251(4) Uani 1 1 d . . . C21 C 0.30593(18) 0.05506(15) 0.56468(12) 0.0269(5) Uani 1 1 d . . . C22 C 0.25259(17) 0.11375(17) 0.51492(12) 0.0269(5) Uani 1 1 d . . . C23 C 0.27387(16) 0.21971(15) 0.51040(11) 0.0220(4) Uani 1 1 d . . . C24 C 0.23777(15) 0.44735(14) 0.55167(10) 0.0182(4) Uani 1 1 d . . . C25 C 0.17778(15) 0.49563(16) 0.49935(10) 0.0197(4) Uani 1 1 d . . . C26 C 0.07451(16) 0.53121(17) 0.50890(12) 0.0259(4) Uani 1 1 d . . . C27 C 0.02502(17) 0.5153(2) 0.57371(13) 0.0336(5) Uani 1 1 d . . . C28 C 0.07927(18) 0.46550(19) 0.62717(12) 0.0321(5) Uani 1 1 d . . . C29 C 0.18278(17) 0.43283(16) 0.61540(11) 0.0235(4) 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 B 0.0218(10) 0.0143(9) 0.0168(10) 0.0000(8) -0.0008(9) -0.0010(8) N1 0.0297(9) 0.0124(7) 0.0192(8) 0.0005(6) -0.0029(7) -0.0019(7) N2 0.0284(9) 0.0138(7) 0.0189(8) 0.0010(7) -0.0034(7) 0.0033(7) N3 0.0275(9) 0.0110(8) 0.0236(8) -0.0011(7) -0.0065(7) 0.0006(7) N4 0.0243(8) 0.0130(7) 0.0201(8) -0.0018(6) -0.0018(7) 0.0000(7) O 0.0245(7) 0.0098(6) 0.0201(7) -0.0014(5) -0.0033(6) -0.0007(5) F1 0.0274(6) 0.0185(6) 0.0271(6) 0.0032(5) 0.0010(5) -0.0026(5) F2 0.0318(7) 0.0373(7) 0.0445(8) 0.0208(7) 0.0041(6) -0.0080(6) F3 0.0280(7) 0.0699(10) 0.0298(7) 0.0150(7) 0.0094(6) -0.0056(7) F4 0.0455(9) 0.0582(9) 0.0404(8) -0.0073(8) 0.0214(7) 0.0106(8) F5 0.0552(9) 0.0250(7) 0.0451(8) -0.0018(6) 0.0235(7) 0.0083(7) F6 0.0504(8) 0.0188(6) 0.0419(8) -0.0069(6) -0.0275(7) 0.0056(6) F7 0.0644(9) 0.0186(6) 0.0316(7) 0.0040(5) -0.0056(7) 0.0106(6) F8 0.0431(7) 0.0136(6) 0.0550(8) -0.0004(6) 0.0116(7) -0.0066(6) F9 0.0345(7) 0.0262(6) 0.0608(9) -0.0170(7) -0.0116(7) -0.0084(6) F10 0.0431(7) 0.0252(6) 0.0315(7) -0.0056(6) -0.0188(6) 0.0018(6) F11 0.0233(6) 0.0340(7) 0.0185(5) 0.0035(5) -0.0022(5) -0.0029(5) F12 0.0247(6) 0.0415(8) 0.0437(8) 0.0041(7) -0.0106(6) 0.0032(6) F13 0.0215(6) 0.0715(11) 0.0629(10) -0.0063(9) 0.0119(7) 0.0088(7) F14 0.0406(8) 0.0781(12) 0.0348(7) 0.0001(8) 0.0227(7) -0.0020(9) F15 0.0381(7) 0.0357(7) 0.0203(6) 0.0063(5) 0.0033(6) -0.0044(6) C1 0.0271(10) 0.0134(9) 0.0143(8) 0.0013(7) -0.0069(8) 0.0019(8) C2 0.0427(13) 0.0112(9) 0.0262(10) -0.0016(8) -0.0015(10) -0.0050(9) C3 0.0439(14) 0.0125(9) 0.0254(10) 0.0002(8) -0.0038(10) 0.0054(9) C4 0.0286(10) 0.0203(10) 0.0238(10) 0.0009(8) 0.0023(9) -0.0027(9) C5 0.0276(11) 0.0313(12) 0.0392(13) 0.0136(10) 0.0065(10) 0.0067(10) C6 0.0417(13) 0.0243(10) 0.0248(11) -0.0015(9) 0.0032(10) 0.0034(10) C7 0.0373(13) 0.0377(13) 0.0353(12) -0.0060(11) 0.0052(11) -0.0135(11) C8 0.0264(10) 0.0212(10) 0.0282(11) 0.0017(8) -0.0020(9) 0.0061(9) C9 0.0314(11) 0.0232(11) 0.0331(12) -0.0025(9) -0.0085(10) 0.0065(9) C10 0.0312(12) 0.0290(11) 0.0347(12) 0.0087(10) 0.0053(10) 0.0038(10) C11 0.0401(13) 0.0343(13) 0.0318(12) -0.0042(10) 0.0011(11) 0.0114(11) C12 0.0175(9) 0.0228(10) 0.0190(9) 0.0007(8) -0.0011(8) -0.0014(8) C13 0.0147(8) 0.0251(10) 0.0224(9) 0.0026(8) -0.0027(8) -0.0014(8) C14 0.0199(10) 0.0333(12) 0.0285(11) 0.0134(10) -0.0029(9) -0.0058(9) C15 0.0162(9) 0.0515(14) 0.0224(10) 0.0088(10) 0.0040(8) -0.0029(10) C16 0.0242(11) 0.0452(14) 0.0260(11) -0.0045(10) 0.0077(9) 0.0032(10) C17 0.0256(10) 0.0263(11) 0.0264(11) -0.0009(9) 0.0024(9) 0.0000(9) C18 0.0217(9) 0.0171(9) 0.0161(9) -0.0024(7) 0.0043(8) -0.0014(8) C19 0.0299(10) 0.0182(10) 0.0198(9) -0.0043(8) -0.0039(9) 0.0006(8) C20 0.0365(12) 0.0168(9) 0.0219(10) 0.0011(8) 0.0030(9) 0.0048(9) C21 0.0317(11) 0.0134(9) 0.0355(12) -0.0034(9) 0.0119(10) -0.0040(9) C22 0.0261(10) 0.0216(10) 0.0329(11) -0.0091(9) 0.0002(9) -0.0056(9) C23 0.0248(10) 0.0187(9) 0.0225(10) -0.0017(8) -0.0032(9) 0.0010(8) C24 0.0199(9) 0.0148(9) 0.0200(9) -0.0031(7) 0.0007(7) -0.0038(8) C25 0.0201(9) 0.0199(9) 0.0191(9) -0.0008(8) 0.0007(8) -0.0055(8) C26 0.0201(10) 0.0254(10) 0.0321(11) -0.0027(9) -0.0048(9) -0.0001(9) C27 0.0195(10) 0.0394(13) 0.0419(13) -0.0079(11) 0.0058(10) 0.0000(10) C28 0.0298(11) 0.0395(13) 0.0271(11) -0.0050(10) 0.0125(10) -0.0056(10) C29 0.0273(10) 0.0220(10) 0.0210(10) -0.0003(8) 0.0016(8) -0.0041(9) _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 B O 1.535(2) . ? B C18 1.642(3) . ? B C24 1.646(3) . ? B C12 1.647(3) . ? N1 C1 1.345(3) . ? N1 C2 1.385(3) . ? N1 C4 1.511(3) . ? N2 C1 1.339(3) . ? N2 C3 1.388(3) . ? N2 C8 1.515(3) . ? N3 N4 1.251(2) . ? N3 C1 1.416(2) . ? N4 O 1.330(2) . ? F1 C13 1.349(2) . ? F2 C14 1.345(3) . ? F3 C15 1.341(2) . ? F4 C16 1.344(3) . ? F5 C17 1.354(3) . ? F6 C19 1.349(2) . ? F7 C20 1.349(2) . ? F8 C21 1.352(2) . ? F9 C22 1.343(2) . ? F10 C23 1.355(2) . ? F11 C25 1.350(2) . ? F12 C26 1.341(2) . ? F13 C27 1.345(3) . ? F14 C28 1.346(2) . ? F15 C29 1.355(2) . ? C2 C3 1.332(3) . ? C4 C6 1.523(3) . ? C4 C7 1.525(3) . ? C4 C5 1.528(3) . ? C8 C11 1.527(3) . ? C8 C9 1.529(3) . ? C8 C10 1.531(3) . ? C12 C17 1.391(3) . ? C12 C13 1.401(3) . ? C13 C14 1.381(3) . ? C14 C15 1.374(3) . ? C15 C16 1.374(4) . ? C16 C17 1.384(3) . ? C18 C19 1.384(3) . ? C18 C23 1.392(3) . ? C19 C20 1.387(3) . ? C20 C21 1.371(3) . ? C21 C22 1.372(3) . ? C22 C23 1.382(3) . ? C24 C25 1.382(3) . ? C24 C29 1.393(3) . ? C25 C26 1.384(3) . ? C26 C27 1.380(3) . ? C27 C28 1.369(3) . ? C28 C29 1.381(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 O B C18 104.97(15) . . ? O B C24 108.58(15) . . ? C18 B C24 105.79(15) . . ? O B C12 108.39(15) . . ? C18 B C12 112.34(16) . . ? C24 B C12 116.16(16) . . ? C1 N1 C2 107.06(18) . . ? C1 N1 C4 127.69(16) . . ? C2 N1 C4 125.05(17) . . ? C1 N2 C3 107.06(17) . . ? C1 N2 C8 128.74(17) . . ? C3 N2 C8 124.19(17) . . ? N4 N3 C1 111.52(15) . . ? N3 N4 O 109.82(15) . . ? N4 O B 114.41(14) . . ? N2 C1 N1 109.62(16) . . ? N2 C1 N3 127.51(19) . . ? N1 C1 N3 122.61(18) . . ? C3 C2 N1 108.06(19) . . ? C2 C3 N2 108.16(19) . . ? N1 C4 C6 107.84(18) . . ? N1 C4 C7 108.40(17) . . ? C6 C4 C7 110.10(19) . . ? N1 C4 C5 109.58(17) . . ? C6 C4 C5 112.22(19) . . ? C7 C4 C5 108.63(19) . . ? N2 C8 C11 108.26(18) . . ? N2 C8 C9 107.28(17) . . ? C11 C8 C9 110.30(18) . . ? N2 C8 C10 109.48(17) . . ? C11 C8 C10 108.76(18) . . ? C9 C8 C10 112.66(18) . . ? C17 C12 C13 113.07(18) . . ? C17 C12 B 124.60(18) . . ? C13 C12 B 122.09(17) . . ? F1 C13 C14 115.69(18) . . ? F1 C13 C12 120.24(17) . . ? C14 C13 C12 124.1(2) . . ? F2 C14 C15 119.72(19) . . ? F2 C14 C13 120.4(2) . . ? C15 C14 C13 119.8(2) . . ? F3 C15 C16 120.1(2) . . ? F3 C15 C14 120.9(2) . . ? C16 C15 C14 119.0(2) . . ? F4 C16 C15 119.9(2) . . ? F4 C16 C17 120.5(2) . . ? C15 C16 C17 119.6(2) . . ? F5 C17 C16 114.3(2) . . ? F5 C17 C12 121.21(19) . . ? C16 C17 C12 124.4(2) . . ? C19 C18 C23 113.34(17) . . ? C19 C18 B 127.10(18) . . ? C23 C18 B 119.52(17) . . ? F6 C19 C18 121.31(18) . . ? F6 C19 C20 114.82(18) . . ? C18 C19 C20 123.9(2) . . ? F7 C20 C21 120.61(18) . . ? F7 C20 C19 119.7(2) . . ? C21 C20 C19 119.7(2) . . ? F8 C21 C20 120.2(2) . . ? F8 C21 C22 120.4(2) . . ? C20 C21 C22 119.38(18) . . ? F9 C22 C21 120.69(19) . . ? F9 C22 C23 120.4(2) . . ? C21 C22 C23 118.87(19) . . ? F10 C23 C22 116.08(18) . . ? F10 C23 C18 119.15(17) . . ? C22 C23 C18 124.75(19) . . ? C25 C24 C29 113.55(18) . . ? C25 C24 B 127.73(17) . . ? C29 C24 B 118.58(17) . . ? F11 C25 C24 121.03(17) . . ? F11 C25 C26 114.63(18) . . ? C24 C25 C26 124.33(19) . . ? F12 C26 C27 119.77(19) . . ? F12 C26 C25 121.12(19) . . ? C27 C26 C25 119.1(2) . . ? F13 C27 C28 121.1(2) . . ? F13 C27 C26 119.5(2) . . ? C28 C27 C26 119.4(2) . . ? F14 C28 C27 120.0(2) . . ? F14 C28 C29 120.7(2) . . ? C27 C28 C29 119.4(2) . . ? F15 C29 C28 116.05(18) . . ? F15 C29 C24 119.72(18) . . ? C28 C29 C24 124.2(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 N3 N4 O 178.14(16) . . . . ? N3 N4 O B 177.01(15) . . . . ? C18 B O N4 -168.33(15) . . . . ? C24 B O N4 -55.6(2) . . . . ? C12 B O N4 71.43(19) . . . . ? C3 N2 C1 N1 2.1(2) . . . . ? C8 N2 C1 N1 -178.62(17) . . . . ? C3 N2 C1 N3 176.32(18) . . . . ? C8 N2 C1 N3 -4.4(3) . . . . ? C2 N1 C1 N2 -2.2(2) . . . . ? C4 N1 C1 N2 -177.40(17) . . . . ? C2 N1 C1 N3 -176.77(17) . . . . ? C4 N1 C1 N3 8.0(3) . . . . ? N4 N3 C1 N2 79.4(2) . . . . ? N4 N3 C1 N1 -107.1(2) . . . . ? C1 N1 C2 C3 1.5(2) . . . . ? C4 N1 C2 C3 176.80(18) . . . . ? N1 C2 C3 N2 -0.2(2) . . . . ? C1 N2 C3 C2 -1.2(2) . . . . ? C8 N2 C3 C2 179.52(18) . . . . ? C1 N1 C4 C6 74.6(2) . . . . ? C2 N1 C4 C6 -99.7(2) . . . . ? C1 N1 C4 C7 -166.18(19) . . . . ? C2 N1 C4 C7 19.5(3) . . . . ? C1 N1 C4 C5 -47.8(3) . . . . ? C2 N1 C4 C5 137.9(2) . . . . ? C1 N2 C8 C11 161.35(19) . . . . ? C3 N2 C8 C11 -19.5(3) . . . . ? C1 N2 C8 C9 -79.6(2) . . . . ? C3 N2 C8 C9 99.5(2) . . . . ? C1 N2 C8 C10 42.9(3) . . . . ? C3 N2 C8 C10 -137.90(19) . . . . ? O B C12 C17 103.8(2) . . . . ? C18 B C12 C17 -11.7(3) . . . . ? C24 B C12 C17 -133.7(2) . . . . ? O B C12 C13 -70.1(2) . . . . ? C18 B C12 C13 174.36(18) . . . . ? C24 B C12 C13 52.4(2) . . . . ? C17 C12 C13 F1 178.51(17) . . . . ? B C12 C13 F1 -7.0(3) . . . . ? C17 C12 C13 C14 -0.9(3) . . . . ? B C12 C13 C14 173.62(18) . . . . ? F1 C13 C14 F2 2.1(3) . . . . ? C12 C13 C14 F2 -178.42(19) . . . . ? F1 C13 C14 C15 -178.29(18) . . . . ? C12 C13 C14 C15 1.2(3) . . . . ? F2 C14 C15 F3 0.6(3) . . . . ? C13 C14 C15 F3 -179.03(19) . . . . ? F2 C14 C15 C16 179.6(2) . . . . ? C13 C14 C15 C16 0.0(3) . . . . ? F3 C15 C16 F4 -0.5(3) . . . . ? C14 C15 C16 F4 -179.52(19) . . . . ? F3 C15 C16 C17 177.79(19) . . . . ? C14 C15 C16 C17 -1.2(3) . . . . ? F4 C16 C17 F5 0.5(3) . . . . ? C15 C16 C17 F5 -177.8(2) . . . . ? F4 C16 C17 C12 179.8(2) . . . . ? C15 C16 C17 C12 1.5(4) . . . . ? C13 C12 C17 F5 178.84(19) . . . . ? B C12 C17 F5 4.5(3) . . . . ? C13 C12 C17 C16 -0.4(3) . . . . ? B C12 C17 C16 -174.8(2) . . . . ? O B C18 C19 -12.0(3) . . . . ? C24 B C18 C19 -126.7(2) . . . . ? C12 B C18 C19 105.6(2) . . . . ? O B C18 C23 165.66(16) . . . . ? C24 B C18 C23 50.9(2) . . . . ? C12 B C18 C23 -76.8(2) . . . . ? C23 C18 C19 F6 175.52(18) . . . . ? B C18 C19 F6 -6.7(3) . . . . ? C23 C18 C19 C20 -3.5(3) . . . . ? B C18 C19 C20 174.2(2) . . . . ? F6 C19 C20 F7 3.4(3) . . . . ? C18 C19 C20 F7 -177.48(18) . . . . ? F6 C19 C20 C21 -176.41(19) . . . . ? C18 C19 C20 C21 2.7(3) . . . . ? F7 C20 C21 F8 0.2(3) . . . . ? C19 C20 C21 F8 179.99(19) . . . . ? F7 C20 C21 C22 -179.57(19) . . . . ? C19 C20 C21 C22 0.3(3) . . . . ? F8 C21 C22 F9 -1.4(3) . . . . ? C20 C21 C22 F9 178.29(19) . . . . ? F8 C21 C22 C23 178.32(19) . . . . ? C20 C21 C22 C23 -1.9(3) . . . . ? F9 C22 C23 F10 -0.9(3) . . . . ? C21 C22 C23 F10 179.32(18) . . . . ? F9 C22 C23 C18 -179.32(19) . . . . ? C21 C22 C23 C18 0.9(3) . . . . ? C19 C18 C23 F10 -176.63(18) . . . . ? B C18 C23 F10 5.4(3) . . . . ? C19 C18 C23 C22 1.7(3) . . . . ? B C18 C23 C22 -176.2(2) . . . . ? O B C24 C25 135.42(19) . . . . ? C18 B C24 C25 -112.4(2) . . . . ? C12 B C24 C25 13.0(3) . . . . ? O B C24 C29 -49.2(2) . . . . ? C18 B C24 C29 63.1(2) . . . . ? C12 B C24 C29 -171.56(17) . . . . ? C29 C24 C25 F11 -175.77(17) . . . . ? B C24 C25 F11 -0.2(3) . . . . ? C29 C24 C25 C26 2.8(3) . . . . ? B C24 C25 C26 178.42(18) . . . . ? F11 C25 C26 F12 -3.0(3) . . . . ? C24 C25 C26 F12 178.34(19) . . . . ? F11 C25 C26 C27 176.39(19) . . . . ? C24 C25 C26 C27 -2.3(3) . . . . ? F12 C26 C27 F13 -0.2(3) . . . . ? C25 C26 C27 F13 -179.56(19) . . . . ? F12 C26 C27 C28 179.9(2) . . . . ? C25 C26 C27 C28 0.4(3) . . . . ? F13 C27 C28 F14 0.4(4) . . . . ? C26 C27 C28 F14 -179.7(2) . . . . ? F13 C27 C28 C29 -179.5(2) . . . . ? C26 C27 C28 C29 0.5(3) . . . . ? F14 C28 C29 F15 0.5(3) . . . . ? C27 C28 C29 F15 -179.6(2) . . . . ? F14 C28 C29 C24 -179.6(2) . . . . ? C27 C28 C29 C24 0.2(3) . . . . ? C25 C24 C29 F15 178.06(17) . . . . ? B C24 C29 F15 2.0(3) . . . . ? C25 C24 C29 C28 -1.8(3) . . . . ? B C24 C29 C28 -177.82(19) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.87 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.244 _refine_diff_density_min -0.147 _refine_diff_density_rms 0.037 _iucr_refine_instructions_details ; TITL eileen36 in P2(1)2(1)2(1) CELL 0.71073 12.5421 12.7742 18.7596 90.000 90.000 90.000 ZERR 4.00 0.0002 0.0002 0.0004 0.000 0.000 0.000 LATT -1 SYMM 1/2 - X, - Y, 1/2 + Z SYMM - X, 1/2 + Y, 1/2 - Z SYMM 1/2 + X, 1/2 - Y, - Z SFAC C H B N O F UNIT 116 80 4 16 4 60 SIZE 0.34 0.20 0.07 TEMP -173 MERG 3 SHEL 999 0.76 ACTA CONF FMAP 2 PLAN 10 L.S. 8 OMIT 0 0 2 OMIT 0 6 3 WGHT 0.026600 0.943700 FVAR 2.42573 B 3 0.359463 0.400216 0.544735 11.00000 0.02182 0.01430 = 0.01675 -0.00002 -0.00077 -0.00103 N1 4 0.573131 0.720530 0.681316 11.00000 0.02972 0.01235 = 0.01923 0.00045 -0.00289 -0.00190 N2 4 0.406663 0.729054 0.716701 11.00000 0.02842 0.01385 = 0.01885 0.00100 -0.00336 0.00329 N3 4 0.475307 0.557074 0.677512 11.00000 0.02754 0.01103 = 0.02365 -0.00114 -0.00649 0.00063 N4 4 0.425559 0.537182 0.621297 11.00000 0.02428 0.01297 = 0.02006 -0.00180 -0.00179 -0.00003 O 5 0.423590 0.434332 0.610434 11.00000 0.02454 0.00985 = 0.02006 -0.00143 -0.00326 -0.00070 F1 6 0.385109 0.615224 0.487249 11.00000 0.02737 0.01853 = 0.02709 0.00315 0.00098 -0.00260 F2 6 0.510779 0.674466 0.381237 11.00000 0.03180 0.03734 = 0.04448 0.02085 0.00413 -0.00801 F3 6 0.620057 0.529913 0.302899 11.00000 0.02801 0.06995 = 0.02980 0.01499 0.00937 -0.00562 F4 6 0.600858 0.323437 0.335197 11.00000 0.04552 0.05821 = 0.04041 -0.00731 0.02142 0.01062 F5 6 0.483900 0.261086 0.443279 11.00000 0.05521 0.02496 = 0.04514 -0.00181 0.02348 0.00834 F6 6 0.481182 0.245102 0.640776 11.00000 0.05044 0.01876 = 0.04195 -0.00693 -0.02750 0.00560 F7 6 0.435169 0.046049 0.656117 11.00000 0.06438 0.01858 = 0.03157 0.00399 -0.00558 0.01055 F8 6 0.285114 -0.048247 0.571769 11.00000 0.04314 0.01365 = 0.05501 -0.00037 0.01161 -0.00661 F9 6 0.180569 0.069291 0.471426 11.00000 0.03454 0.02616 = 0.06083 -0.01699 -0.01157 -0.00840 F10 6 0.219486 0.273198 0.459705 11.00000 0.04310 0.02519 = 0.03151 -0.00561 -0.01878 0.00180 F11 6 0.216968 0.509537 0.432976 11.00000 0.02328 0.03405 = 0.01846 0.00353 -0.00216 -0.00294 F12 6 0.021909 0.579730 0.456189 11.00000 0.02468 0.04150 = 0.04371 0.00408 -0.01064 0.00324 F13 6 -0.075582 0.549030 0.583311 11.00000 0.02152 0.07150 = 0.06288 -0.00625 0.01191 0.00881 F14 6 0.031746 0.449032 0.690523 11.00000 0.04059 0.07807 = 0.03480 0.00012 0.02270 -0.00197 F15 6 0.231162 0.383573 0.670562 11.00000 0.03812 0.03569 = 0.02035 0.00633 0.00334 -0.00442 C1 1 0.482069 0.666280 0.689790 11.00000 0.02708 0.01337 = 0.01426 0.00129 -0.00685 0.00193 C2 1 0.552300 0.822774 0.701483 11.00000 0.04268 0.01117 = 0.02616 -0.00163 -0.00151 -0.00501 AFIX 43 H2 2 0.601462 0.879315 0.700131 11.00000 -1.20000 AFIX 0 C3 1 0.451290 0.828000 0.723110 11.00000 0.04391 0.01251 = 0.02540 0.00018 -0.00377 0.00544 AFIX 43 H3 2 0.415929 0.888913 0.739995 11.00000 -1.20000 AFIX 0 C4 1 0.677082 0.682221 0.650002 11.00000 0.02861 0.02026 = 0.02375 0.00092 0.00234 -0.00270 C5 1 0.706586 0.576929 0.683267 11.00000 0.02755 0.03134 = 0.03919 0.01363 0.00653 0.00672 AFIX 137 H5A 2 0.703353 0.582470 0.735325 11.00000 -1.50000 H5B 2 0.779009 0.557553 0.668760 11.00000 -1.50000 H5C 2 0.656317 0.523243 0.667047 11.00000 -1.50000 AFIX 0 C6 1 0.663144 0.674848 0.569535 11.00000 0.04172 0.02431 = 0.02481 -0.00151 0.00320 0.00338 AFIX 137 H6A 2 0.607049 0.623971 0.558476 11.00000 -1.50000 H6B 2 0.730312 0.652239 0.547732 11.00000 -1.50000 H6C 2 0.643099 0.743588 0.550603 11.00000 -1.50000 AFIX 0 C7 1 0.764018 0.761363 0.668095 11.00000 0.03728 0.03775 = 0.03534 -0.00601 0.00517 -0.01346 AFIX 137 H7A 2 0.745684 0.829519 0.647483 11.00000 -1.50000 H7B 2 0.832192 0.737440 0.648443 11.00000 -1.50000 H7C 2 0.770039 0.767983 0.719984 11.00000 -1.50000 AFIX 0 C8 1 0.292703 0.702634 0.736610 11.00000 0.02640 0.02117 = 0.02819 0.00172 -0.00197 0.00614 C9 1 0.227670 0.701393 0.667668 11.00000 0.03137 0.02324 = 0.03305 -0.00251 -0.00845 0.00647 AFIX 137 H9A 2 0.232110 0.770113 0.644635 11.00000 -1.50000 H9B 2 0.153035 0.685454 0.678682 11.00000 -1.50000 H9C 2 0.256188 0.647818 0.635502 11.00000 -1.50000 AFIX 0 C10 1 0.290118 0.597476 0.775763 11.00000 0.03120 0.02898 = 0.03474 0.00873 0.00529 0.00375 AFIX 137 H10A 2 0.308347 0.541148 0.742457 11.00000 -1.50000 H10B 2 0.218501 0.585454 0.794982 11.00000 -1.50000 H10C 2 0.341853 0.598529 0.814906 11.00000 -1.50000 AFIX 0 C11 1 0.251386 0.787660 0.786708 11.00000 0.04012 0.03433 = 0.03180 -0.00421 0.00105 0.01143 AFIX 137 H11A 2 0.299403 0.794025 0.827691 11.00000 -1.50000 H11B 2 0.179812 0.768944 0.803343 11.00000 -1.50000 H11C 2 0.248426 0.854582 0.761243 11.00000 -1.50000 AFIX 0 C12 1 0.426406 0.434246 0.472848 11.00000 0.01745 0.02281 = 0.01902 0.00071 -0.00115 -0.00139 C13 1 0.438204 0.539054 0.452313 11.00000 0.01468 0.02513 = 0.02242 0.00262 -0.00270 -0.00141 C14 1 0.501742 0.571964 0.396541 11.00000 0.01986 0.03333 = 0.02845 0.01338 -0.00291 -0.00577 C15 1 0.556693 0.499646 0.356640 11.00000 0.01619 0.05153 = 0.02242 0.00879 0.00401 -0.00293 C16 1 0.547134 0.395311 0.373278 11.00000 0.02421 0.04519 = 0.02598 -0.00446 0.00770 0.00319 C17 1 0.484346 0.365379 0.430423 11.00000 0.02558 0.02628 = 0.02642 -0.00087 0.00241 -0.00002 C18 1 0.347624 0.272715 0.552453 11.00000 0.02173 0.01714 = 0.01609 -0.00241 0.00430 -0.00140 C19 1 0.401762 0.208118 0.599325 11.00000 0.02990 0.01820 = 0.01979 -0.00434 -0.00393 0.00061 C20 1 0.381053 0.102057 0.607080 11.00000 0.03655 0.01676 = 0.02194 0.00111 0.00303 0.00483 C21 1 0.305930 0.055057 0.564678 11.00000 0.03171 0.01342 = 0.03553 -0.00337 0.01193 -0.00402 C22 1 0.252587 0.113747 0.514917 11.00000 0.02609 0.02165 = 0.03293 -0.00914 0.00023 -0.00558 C23 1 0.273871 0.219709 0.510396 11.00000 0.02485 0.01871 = 0.02248 -0.00172 -0.00317 0.00102 C24 1 0.237771 0.447354 0.551669 11.00000 0.01992 0.01478 = 0.02002 -0.00313 0.00067 -0.00382 C25 1 0.177781 0.495630 0.499345 11.00000 0.02005 0.01992 = 0.01911 -0.00081 0.00069 -0.00547 C26 1 0.074509 0.531212 0.508897 11.00000 0.02008 0.02541 = 0.03213 -0.00271 -0.00478 -0.00007 C27 1 0.025024 0.515333 0.573707 11.00000 0.01946 0.03943 = 0.04190 -0.00795 0.00582 0.00002 C28 1 0.079274 0.465504 0.627170 11.00000 0.02976 0.03953 = 0.02711 -0.00500 0.01245 -0.00558 C29 1 0.182777 0.432827 0.615397 11.00000 0.02735 0.02200 = 0.02102 -0.00030 0.00157 -0.00410 HKLF 4 ; _database_code_depnum_ccdc_archive 'CCDC 963625' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_eileen19a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C31 H24 B F15 N4 O' _chemical_formula_weight 764.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.5262(4) _cell_length_b 18.5035(8) _cell_length_c 17.6858(8) _cell_angle_alpha 90.00 _cell_angle_beta 92.377(4) _cell_angle_gamma 90.00 _cell_volume 3114.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 16519 _cell_measurement_theta_min 3.4556 _cell_measurement_theta_max 75.9199 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.630 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1544 _exptl_absorpt_coefficient_mu 1.452 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.79885 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'Nova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Xcalibur, Atlas, Nova' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3543 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 48520 _diffrn_reflns_av_R_equivalents 0.0686 _diffrn_reflns_av_sigmaI/netI 0.0313 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.46 _diffrn_reflns_theta_max 74.49 _reflns_number_total 6363 _reflns_number_gt 5281 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker XP' _computing_publication_material SHELXL-97 _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^)+(0.0593P)^2^+0.8062P] 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 6363 _refine_ls_number_parameters 477 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0496 _refine_ls_R_factor_gt 0.0396 _refine_ls_wR_factor_ref 0.1084 _refine_ls_wR_factor_gt 0.1011 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _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 B B 0.46929(19) 0.51557(10) 0.74058(11) 0.0237(4) Uani 1 1 d . . . N1 N 0.78937(14) 0.35129(7) 0.58312(8) 0.0228(3) Uani 1 1 d . . . N2 N 0.59382(14) 0.30543(7) 0.53183(8) 0.0220(3) Uani 1 1 d . . . N3 N 0.58059(15) 0.42893(8) 0.57735(8) 0.0254(3) Uani 1 1 d . . . N4 N 0.56594(15) 0.43714(8) 0.64725(8) 0.0256(3) Uani 1 1 d . . . O O 0.49382(12) 0.49748(6) 0.65819(7) 0.0249(2) Uani 1 1 d . . . F1 F 0.61386(11) 0.42454(6) 0.86692(6) 0.0341(2) Uani 1 1 d . . . F2 F 0.87337(12) 0.44279(6) 0.92246(6) 0.0361(3) Uani 1 1 d . . . F3 F 1.03857(11) 0.55055(6) 0.87093(7) 0.0362(3) Uani 1 1 d . . . F4 F 0.93689(11) 0.63874(6) 0.75818(7) 0.0347(2) Uani 1 1 d . . . F5 F 0.67650(11) 0.62159(6) 0.70041(6) 0.0291(2) Uani 1 1 d . . . F6 F 0.51045(11) 0.66210(6) 0.82111(6) 0.0300(2) Uani 1 1 d . . . F7 F 0.37136(12) 0.78228(6) 0.78570(6) 0.0334(2) Uani 1 1 d . . . F8 F 0.15701(12) 0.78142(6) 0.67873(7) 0.0375(3) Uani 1 1 d . . . F9 F 0.08423(12) 0.65510(6) 0.60836(7) 0.0371(3) Uani 1 1 d . . . F10 F 0.22269(11) 0.53395(6) 0.64162(6) 0.0334(2) Uani 1 1 d . . . F11 F 0.38831(12) 0.53022(6) 0.89280(6) 0.0349(2) Uani 1 1 d . . . F12 F 0.22758(13) 0.44211(7) 0.97246(6) 0.0409(3) Uani 1 1 d . . . F13 F 0.11679(12) 0.32001(6) 0.90763(7) 0.0380(3) Uani 1 1 d . . . F14 F 0.17233(12) 0.28835(6) 0.76124(7) 0.0358(3) Uani 1 1 d . . . F15 F 0.32698(11) 0.37550(6) 0.68099(6) 0.0310(2) Uani 1 1 d . . . C1 C 0.65343(17) 0.36448(9) 0.56382(9) 0.0224(3) Uani 1 1 d . . . C2 C 0.81353(17) 0.27810(9) 0.56843(10) 0.0246(3) Uani 1 1 d . . . C3 C 0.69401(17) 0.25020(9) 0.53655(9) 0.0236(3) Uani 1 1 d . . . C4 C 0.89829(17) 0.40737(9) 0.60895(10) 0.0240(3) Uani 1 1 d . . . C5 C 0.85491(19) 0.48318(9) 0.58147(11) 0.0299(4) Uani 1 1 d . . . H5A H 0.7773 0.5008 0.6111 0.045 Uiso 1 1 calc R . . H5B H 0.8247 0.4810 0.5279 0.045 Uiso 1 1 calc R . . H5C H 0.9351 0.5161 0.5879 0.045 Uiso 1 1 calc R . . C6 C 0.91414(18) 0.40517(10) 0.69472(10) 0.0291(4) Uani 1 1 d . . . H6A H 0.8233 0.4156 0.7164 0.044 Uiso 1 1 calc R . . H6B H 0.9831 0.4415 0.7122 0.044 Uiso 1 1 calc R . . H6C H 0.9463 0.3571 0.7109 0.044 Uiso 1 1 calc R . . C7 C 1.03751(18) 0.38978(10) 0.57238(10) 0.0293(4) Uani 1 1 d . . . H7A H 1.1017 0.4309 0.5787 0.044 Uiso 1 1 calc R . . H7B H 1.0199 0.3802 0.5183 0.044 Uiso 1 1 calc R . . H7C H 1.0799 0.3470 0.5968 0.044 Uiso 1 1 calc R . . C8 C 0.94410(19) 0.23649(10) 0.58961(13) 0.0353(4) Uani 1 1 d . . . H8A H 0.9206 0.1853 0.5956 0.053 Uiso 1 1 calc R . . H8B H 0.9854 0.2552 0.6374 0.053 Uiso 1 1 calc R . . H8C H 1.0117 0.2417 0.5497 0.053 Uiso 1 1 calc R . . C9 C 0.67466(19) 0.17347(9) 0.51135(11) 0.0303(4) Uani 1 1 d . . . H9A H 0.6956 0.1694 0.4577 0.046 Uiso 1 1 calc R . . H9B H 0.5773 0.1586 0.5184 0.046 Uiso 1 1 calc R . . H9C H 0.7384 0.1422 0.5414 0.046 Uiso 1 1 calc R . . C10 C 0.44623(17) 0.29893(9) 0.49521(9) 0.0231(3) Uani 1 1 d . . . C11 C 0.37453(18) 0.37265(9) 0.48574(10) 0.0263(3) Uani 1 1 d . . . H11A H 0.3554 0.3925 0.5357 0.039 Uiso 1 1 calc R . . H11B H 0.2860 0.3670 0.4561 0.039 Uiso 1 1 calc R . . H11C H 0.4364 0.4057 0.4594 0.039 Uiso 1 1 calc R . . C12 C 0.35721(17) 0.25078(10) 0.54475(10) 0.0267(3) Uani 1 1 d . . . H12A H 0.3987 0.2023 0.5479 0.040 Uiso 1 1 calc R . . H12B H 0.2615 0.2476 0.5225 0.040 Uiso 1 1 calc R . . H12C H 0.3545 0.2716 0.5956 0.040 Uiso 1 1 calc R . . C13 C 0.46061(19) 0.26783(10) 0.41562(10) 0.0280(3) Uani 1 1 d . . . H13A H 0.5244 0.2982 0.3874 0.042 Uiso 1 1 calc R . . H13B H 0.3682 0.2667 0.3892 0.042 Uiso 1 1 calc R . . H13C H 0.4984 0.2186 0.4194 0.042 Uiso 1 1 calc R . . C14 C 0.62718(17) 0.52424(9) 0.78242(9) 0.0238(3) Uani 1 1 d . . . C15 C 0.68637(18) 0.48053(9) 0.83879(10) 0.0264(3) Uani 1 1 d . . . C16 C 0.82229(19) 0.48815(10) 0.86943(10) 0.0280(3) Uani 1 1 d . . . C17 C 0.90638(18) 0.54221(10) 0.84282(10) 0.0285(4) Uani 1 1 d . . . C18 C 0.85452(18) 0.58666(9) 0.78562(10) 0.0270(3) Uani 1 1 d . . . C19 C 0.71915(18) 0.57670(9) 0.75706(9) 0.0248(3) Uani 1 1 d . . . C20 C 0.37986(17) 0.59171(9) 0.73060(9) 0.0236(3) Uani 1 1 d . . . C21 C 0.40653(17) 0.65678(9) 0.76728(9) 0.0246(3) Uani 1 1 d . . . C22 C 0.33405(18) 0.72034(9) 0.75114(10) 0.0263(3) Uani 1 1 d . . . C23 C 0.22548(19) 0.72031(10) 0.69661(10) 0.0280(4) Uani 1 1 d . . . C24 C 0.19104(18) 0.65639(10) 0.66063(10) 0.0277(4) Uani 1 1 d . . . C25 C 0.26617(18) 0.59464(9) 0.67834(10) 0.0265(3) Uani 1 1 d . . . C26 C 0.36860(17) 0.45753(9) 0.78327(10) 0.0251(3) Uani 1 1 d . . . C27 C 0.33519(19) 0.47079(9) 0.85781(10) 0.0281(4) Uani 1 1 d . . . C28 C 0.25257(19) 0.42641(10) 0.90038(10) 0.0302(4) Uani 1 1 d . . . C29 C 0.19653(18) 0.36455(10) 0.86763(11) 0.0305(4) Uani 1 1 d . . . C30 C 0.22501(18) 0.34880(9) 0.79381(11) 0.0285(4) Uani 1 1 d . . . C31 C 0.30834(17) 0.39509(9) 0.75326(10) 0.0254(3) 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 B 0.0219(9) 0.0239(8) 0.0253(9) -0.0017(7) -0.0013(7) -0.0003(7) N1 0.0177(6) 0.0226(7) 0.0279(7) 0.0003(5) 0.0005(5) 0.0004(5) N2 0.0169(6) 0.0231(6) 0.0259(7) 0.0004(5) 0.0000(5) 0.0012(5) N3 0.0219(7) 0.0256(7) 0.0287(7) -0.0019(5) -0.0005(5) 0.0001(5) N4 0.0200(6) 0.0252(7) 0.0315(8) -0.0016(6) 0.0000(5) 0.0003(5) O 0.0229(6) 0.0236(6) 0.0281(6) -0.0023(4) 0.0012(4) 0.0019(4) F1 0.0280(5) 0.0320(5) 0.0422(6) 0.0132(4) -0.0023(4) -0.0033(4) F2 0.0315(6) 0.0368(6) 0.0391(6) 0.0093(5) -0.0083(4) 0.0028(5) F3 0.0232(5) 0.0359(6) 0.0485(7) 0.0001(5) -0.0091(4) 0.0003(4) F4 0.0250(5) 0.0323(5) 0.0466(6) 0.0062(5) 0.0001(4) -0.0060(4) F5 0.0255(5) 0.0304(5) 0.0312(5) 0.0075(4) -0.0016(4) -0.0013(4) F6 0.0296(5) 0.0305(5) 0.0293(5) -0.0063(4) -0.0068(4) 0.0012(4) F7 0.0386(6) 0.0253(5) 0.0363(6) -0.0074(4) 0.0010(4) 0.0012(4) F8 0.0386(6) 0.0318(6) 0.0418(6) -0.0001(4) -0.0017(5) 0.0136(5) F9 0.0278(5) 0.0426(6) 0.0399(6) -0.0033(5) -0.0112(4) 0.0069(5) F10 0.0271(5) 0.0298(5) 0.0425(6) -0.0081(4) -0.0082(4) -0.0005(4) F11 0.0405(6) 0.0323(5) 0.0323(6) -0.0081(4) 0.0055(4) -0.0041(5) F12 0.0430(7) 0.0494(7) 0.0311(6) -0.0010(5) 0.0109(5) -0.0019(5) F13 0.0282(5) 0.0423(6) 0.0436(6) 0.0131(5) 0.0042(5) -0.0051(5) F14 0.0319(6) 0.0287(5) 0.0464(6) 0.0001(5) -0.0030(5) -0.0084(4) F15 0.0309(5) 0.0321(5) 0.0299(5) -0.0057(4) 0.0003(4) -0.0048(4) C1 0.0181(7) 0.0228(7) 0.0262(8) 0.0009(6) 0.0019(6) 0.0004(6) C2 0.0207(8) 0.0228(8) 0.0303(8) 0.0000(6) 0.0026(6) 0.0015(6) C3 0.0208(8) 0.0223(7) 0.0279(8) 0.0010(6) 0.0024(6) 0.0032(6) C4 0.0185(7) 0.0233(8) 0.0301(8) -0.0015(6) 0.0005(6) -0.0033(6) C5 0.0265(8) 0.0241(8) 0.0389(10) 0.0038(7) -0.0011(7) -0.0039(7) C6 0.0243(8) 0.0326(9) 0.0302(9) -0.0023(7) -0.0004(7) 0.0003(7) C7 0.0209(8) 0.0333(9) 0.0337(9) -0.0038(7) 0.0036(7) -0.0051(7) C8 0.0239(9) 0.0259(9) 0.0552(12) -0.0015(8) -0.0070(8) 0.0031(7) C9 0.0260(8) 0.0231(8) 0.0416(10) -0.0035(7) -0.0026(7) 0.0022(7) C10 0.0169(7) 0.0262(8) 0.0259(8) 0.0002(6) -0.0024(6) -0.0015(6) C11 0.0208(8) 0.0281(8) 0.0296(8) 0.0003(6) -0.0027(6) 0.0027(6) C12 0.0202(8) 0.0306(8) 0.0291(8) 0.0014(6) -0.0002(6) -0.0030(6) C13 0.0271(8) 0.0305(8) 0.0261(8) -0.0011(7) -0.0012(6) -0.0008(7) C14 0.0230(8) 0.0241(8) 0.0243(8) -0.0029(6) 0.0014(6) 0.0006(6) C15 0.0260(8) 0.0249(8) 0.0283(8) 0.0007(6) 0.0026(6) -0.0006(7) C16 0.0286(9) 0.0285(8) 0.0266(8) 0.0012(7) -0.0025(7) 0.0040(7) C17 0.0215(8) 0.0305(8) 0.0331(9) -0.0057(7) -0.0034(6) 0.0017(7) C18 0.0244(8) 0.0251(8) 0.0315(9) -0.0008(6) 0.0024(7) -0.0023(6) C19 0.0255(8) 0.0245(8) 0.0243(8) 0.0002(6) 0.0006(6) 0.0023(6) C20 0.0218(8) 0.0252(8) 0.0239(8) -0.0016(6) 0.0025(6) 0.0007(6) C21 0.0212(8) 0.0292(8) 0.0233(8) -0.0009(6) 0.0003(6) 0.0006(6) C22 0.0266(8) 0.0249(8) 0.0276(8) -0.0039(6) 0.0057(6) 0.0003(6) C23 0.0260(8) 0.0272(8) 0.0312(9) 0.0020(7) 0.0048(7) 0.0070(7) C24 0.0208(8) 0.0344(9) 0.0277(8) -0.0003(7) -0.0011(6) 0.0028(7) C25 0.0225(8) 0.0258(8) 0.0311(9) -0.0046(7) 0.0013(6) -0.0003(6) C26 0.0199(7) 0.0260(8) 0.0293(8) 0.0006(6) -0.0001(6) 0.0020(6) C27 0.0257(8) 0.0260(8) 0.0326(9) -0.0019(7) 0.0015(7) 0.0011(7) C28 0.0256(8) 0.0355(9) 0.0297(9) 0.0017(7) 0.0032(7) 0.0041(7) C29 0.0207(8) 0.0325(9) 0.0382(10) 0.0105(7) 0.0010(7) 0.0005(7) C30 0.0216(8) 0.0252(8) 0.0381(10) 0.0024(7) -0.0048(7) 0.0000(6) C31 0.0205(8) 0.0273(8) 0.0283(8) -0.0001(6) -0.0007(6) 0.0010(6) _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 B O 1.523(2) . ? B C26 1.644(2) . ? B C20 1.652(2) . ? B C14 1.656(2) . ? N1 C1 1.348(2) . ? N1 C2 1.400(2) . ? N1 C4 1.524(2) . ? N2 C1 1.345(2) . ? N2 C3 1.399(2) . ? N2 C10 1.528(2) . ? N3 N4 1.259(2) . ? N3 C1 1.405(2) . ? N4 O 1.3293(18) . ? F1 C15 1.352(2) . ? F2 C16 1.335(2) . ? F3 C17 1.343(2) . ? F4 C18 1.346(2) . ? F5 C19 1.3509(19) . ? F6 C21 1.3482(19) . ? F7 C22 1.340(2) . ? F8 C23 1.337(2) . ? F9 C24 1.346(2) . ? F10 C25 1.354(2) . ? F11 C27 1.350(2) . ? F12 C28 1.339(2) . ? F13 C29 1.342(2) . ? F14 C30 1.346(2) . ? F15 C31 1.347(2) . ? C2 C3 1.352(2) . ? C2 C8 1.497(2) . ? C3 C9 1.497(2) . ? C4 C6 1.519(2) . ? C4 C7 1.534(2) . ? C4 C5 1.536(2) . ? C10 C12 1.530(2) . ? C10 C11 1.532(2) . ? C10 C13 1.532(2) . ? C14 C15 1.385(2) . ? C14 C19 1.394(2) . ? C15 C16 1.390(2) . ? C16 C17 1.377(3) . ? C17 C18 1.379(3) . ? C18 C19 1.378(2) . ? C20 C21 1.386(2) . ? C20 C25 1.395(2) . ? C21 C22 1.388(2) . ? C22 C23 1.385(3) . ? C23 C24 1.376(3) . ? C24 C25 1.377(2) . ? C26 C31 1.386(2) . ? C26 C27 1.391(3) . ? C27 C28 1.382(3) . ? C28 C29 1.380(3) . ? C29 C30 1.376(3) . ? C30 C31 1.388(2) . ? 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 O B C26 114.30(13) . . ? O B C20 100.61(13) . . ? C26 B C20 107.34(13) . . ? O B C14 106.04(13) . . ? C26 B C14 113.23(14) . . ? C20 B C14 114.83(14) . . ? C1 N1 C2 106.97(14) . . ? C1 N1 C4 125.99(14) . . ? C2 N1 C4 126.81(14) . . ? C1 N2 C3 107.05(13) . . ? C1 N2 C10 127.38(14) . . ? C3 N2 C10 125.55(14) . . ? N4 N3 C1 110.20(14) . . ? N3 N4 O 108.86(13) . . ? N4 O B 115.13(12) . . ? N2 C1 N1 110.11(14) . . ? N2 C1 N3 123.93(15) . . ? N1 C1 N3 125.91(15) . . ? C3 C2 N1 107.74(14) . . ? C3 C2 C8 125.77(16) . . ? N1 C2 C8 126.33(15) . . ? C2 C3 N2 107.86(14) . . ? C2 C3 C9 125.28(15) . . ? N2 C3 C9 126.86(15) . . ? C6 C4 N1 108.63(13) . . ? C6 C4 C7 111.31(14) . . ? N1 C4 C7 108.58(13) . . ? C6 C4 C5 110.79(14) . . ? N1 C4 C5 110.86(13) . . ? C7 C4 C5 106.64(14) . . ? N2 C10 C12 108.97(13) . . ? N2 C10 C11 112.00(13) . . ? C12 C10 C11 109.02(14) . . ? N2 C10 C13 107.65(13) . . ? C12 C10 C13 112.34(14) . . ? C11 C10 C13 106.89(14) . . ? C15 C14 C19 113.30(15) . . ? C15 C14 B 126.87(15) . . ? C19 C14 B 119.66(15) . . ? F1 C15 C14 120.89(15) . . ? F1 C15 C16 114.60(15) . . ? C14 C15 C16 124.49(16) . . ? F2 C16 C17 119.77(16) . . ? F2 C16 C15 121.10(16) . . ? C17 C16 C15 119.10(16) . . ? F3 C17 C16 120.45(16) . . ? F3 C17 C18 120.31(16) . . ? C16 C17 C18 119.22(16) . . ? F4 C18 C19 120.95(16) . . ? F4 C18 C17 119.67(16) . . ? C19 C18 C17 119.37(16) . . ? F5 C19 C18 115.97(15) . . ? F5 C19 C14 119.54(15) . . ? C18 C19 C14 124.49(16) . . ? C21 C20 C25 113.47(15) . . ? C21 C20 B 127.38(15) . . ? C25 C20 B 119.12(15) . . ? F6 C21 C20 120.59(15) . . ? F6 C21 C22 115.34(15) . . ? C20 C21 C22 124.05(16) . . ? F7 C22 C23 119.64(16) . . ? F7 C22 C21 120.71(16) . . ? C23 C22 C21 119.60(16) . . ? F8 C23 C24 120.86(16) . . ? F8 C23 C22 120.49(16) . . ? C24 C23 C22 118.64(16) . . ? F9 C24 C23 119.45(16) . . ? F9 C24 C25 120.81(16) . . ? C23 C24 C25 119.74(16) . . ? F10 C25 C24 115.68(15) . . ? F10 C25 C20 119.94(15) . . ? C24 C25 C20 124.37(16) . . ? C31 C26 C27 113.75(16) . . ? C31 C26 B 127.51(15) . . ? C27 C26 B 118.74(15) . . ? F11 C27 C28 116.45(16) . . ? F11 C27 C26 118.82(16) . . ? C28 C27 C26 124.71(17) . . ? F12 C28 C29 119.92(16) . . ? F12 C28 C27 121.18(17) . . ? C29 C28 C27 118.90(17) . . ? F13 C29 C30 120.56(17) . . ? F13 C29 C28 120.37(17) . . ? C30 C29 C28 119.07(17) . . ? F14 C30 C29 119.84(16) . . ? F14 C30 C31 120.20(16) . . ? C29 C30 C31 119.96(17) . . ? F15 C31 C26 121.25(15) . . ? F15 C31 C30 115.15(15) . . ? C26 C31 C30 123.60(16) . . ? 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 C1 N3 N4 O -178.47(12) . . . . ? N3 N4 O B -179.10(13) . . . . ? C26 B O N4 -65.54(18) . . . . ? C20 B O N4 179.80(12) . . . . ? C14 B O N4 59.91(16) . . . . ? C3 N2 C1 N1 4.85(18) . . . . ? C10 N2 C1 N1 -173.82(14) . . . . ? C3 N2 C1 N3 -172.73(15) . . . . ? C10 N2 C1 N3 8.6(3) . . . . ? C2 N1 C1 N2 -5.25(18) . . . . ? C4 N1 C1 N2 169.59(14) . . . . ? C2 N1 C1 N3 172.28(15) . . . . ? C4 N1 C1 N3 -12.9(3) . . . . ? N4 N3 C1 N2 109.21(18) . . . . ? N4 N3 C1 N1 -68.0(2) . . . . ? C1 N1 C2 C3 3.56(19) . . . . ? C4 N1 C2 C3 -171.22(15) . . . . ? C1 N1 C2 C8 -172.04(17) . . . . ? C4 N1 C2 C8 13.2(3) . . . . ? N1 C2 C3 N2 -0.65(19) . . . . ? C8 C2 C3 N2 174.99(17) . . . . ? N1 C2 C3 C9 179.48(16) . . . . ? C8 C2 C3 C9 -4.9(3) . . . . ? C1 N2 C3 C2 -2.51(18) . . . . ? C10 N2 C3 C2 176.19(14) . . . . ? C1 N2 C3 C9 177.36(16) . . . . ? C10 N2 C3 C9 -3.9(3) . . . . ? C1 N1 C4 C6 99.37(18) . . . . ? C2 N1 C4 C6 -86.80(19) . . . . ? C1 N1 C4 C7 -139.43(16) . . . . ? C2 N1 C4 C7 34.4(2) . . . . ? C1 N1 C4 C5 -22.6(2) . . . . ? C2 N1 C4 C5 151.24(16) . . . . ? C1 N2 C10 C12 -110.97(18) . . . . ? C3 N2 C10 C12 70.59(19) . . . . ? C1 N2 C10 C11 9.7(2) . . . . ? C3 N2 C10 C11 -168.70(15) . . . . ? C1 N2 C10 C13 126.95(17) . . . . ? C3 N2 C10 C13 -51.5(2) . . . . ? O B C14 C15 -114.64(18) . . . . ? C26 B C14 C15 11.5(2) . . . . ? C20 B C14 C15 135.23(17) . . . . ? O B C14 C19 60.20(19) . . . . ? C26 B C14 C19 -173.69(14) . . . . ? C20 B C14 C19 -49.9(2) . . . . ? C19 C14 C15 F1 -176.54(15) . . . . ? B C14 C15 F1 -1.4(3) . . . . ? C19 C14 C15 C16 1.6(2) . . . . ? B C14 C15 C16 176.70(16) . . . . ? F1 C15 C16 F2 -0.1(2) . . . . ? C14 C15 C16 F2 -178.36(16) . . . . ? F1 C15 C16 C17 177.97(15) . . . . ? C14 C15 C16 C17 -0.3(3) . . . . ? F2 C16 C17 F3 -1.4(3) . . . . ? C15 C16 C17 F3 -179.49(16) . . . . ? F2 C16 C17 C18 177.08(16) . . . . ? C15 C16 C17 C18 -1.1(3) . . . . ? F3 C17 C18 F4 -0.2(3) . . . . ? C16 C17 C18 F4 -178.67(16) . . . . ? F3 C17 C18 C19 179.32(15) . . . . ? C16 C17 C18 C19 0.9(3) . . . . ? F4 C18 C19 F5 0.5(2) . . . . ? C17 C18 C19 F5 -179.06(15) . . . . ? F4 C18 C19 C14 -179.84(15) . . . . ? C17 C18 C19 C14 0.6(3) . . . . ? C15 C14 C19 F5 177.89(14) . . . . ? B C14 C19 F5 2.4(2) . . . . ? C15 C14 C19 C18 -1.8(2) . . . . ? B C14 C19 C18 -177.27(16) . . . . ? O B C20 C21 -129.29(17) . . . . ? C26 B C20 C21 110.90(18) . . . . ? C14 B C20 C21 -15.9(2) . . . . ? O B C20 C25 48.48(19) . . . . ? C26 B C20 C25 -71.32(19) . . . . ? C14 B C20 C25 161.83(15) . . . . ? C25 C20 C21 F6 178.00(14) . . . . ? B C20 C21 F6 -4.1(3) . . . . ? C25 C20 C21 C22 -3.8(2) . . . . ? B C20 C21 C22 174.12(16) . . . . ? F6 C21 C22 F7 2.5(2) . . . . ? C20 C21 C22 F7 -175.86(15) . . . . ? F6 C21 C22 C23 179.98(15) . . . . ? C20 C21 C22 C23 1.6(3) . . . . ? F7 C22 C23 F8 -0.6(2) . . . . ? C21 C22 C23 F8 -178.10(15) . . . . ? F7 C22 C23 C24 178.55(15) . . . . ? C21 C22 C23 C24 1.0(3) . . . . ? F8 C23 C24 F9 -2.0(3) . . . . ? C22 C23 C24 F9 178.90(15) . . . . ? F8 C23 C24 C25 177.90(16) . . . . ? C22 C23 C24 C25 -1.2(3) . . . . ? F9 C24 C25 F10 -1.8(2) . . . . ? C23 C24 C25 F10 178.36(15) . . . . ? F9 C24 C25 C20 178.65(16) . . . . ? C23 C24 C25 C20 -1.2(3) . . . . ? C21 C20 C25 F10 -176.01(15) . . . . ? B C20 C25 F10 5.9(2) . . . . ? C21 C20 C25 C24 3.6(3) . . . . ? B C20 C25 C24 -174.50(16) . . . . ? O B C26 C31 1.5(2) . . . . ? C20 B C26 C31 112.11(18) . . . . ? C14 B C26 C31 -120.12(18) . . . . ? O B C26 C27 -177.45(14) . . . . ? C20 B C26 C27 -66.80(19) . . . . ? C14 B C26 C27 61.0(2) . . . . ? C31 C26 C27 F11 179.96(15) . . . . ? B C26 C27 F11 -1.0(2) . . . . ? C31 C26 C27 C28 1.3(3) . . . . ? B C26 C27 C28 -179.61(16) . . . . ? F11 C27 C28 F12 -0.1(3) . . . . ? C26 C27 C28 F12 178.55(16) . . . . ? F11 C27 C28 C29 -179.44(16) . . . . ? C26 C27 C28 C29 -0.8(3) . . . . ? F12 C28 C29 F13 0.1(3) . . . . ? C27 C28 C29 F13 179.46(16) . . . . ? F12 C28 C29 C30 -179.09(16) . . . . ? C27 C28 C29 C30 0.3(3) . . . . ? F13 C29 C30 F14 0.2(3) . . . . ? C28 C29 C30 F14 179.36(15) . . . . ? F13 C29 C30 C31 -179.59(15) . . . . ? C28 C29 C30 C31 -0.4(3) . . . . ? C27 C26 C31 F15 178.11(15) . . . . ? B C26 C31 F15 -0.8(3) . . . . ? C27 C26 C31 C30 -1.5(2) . . . . ? B C26 C31 C30 179.59(16) . . . . ? F14 C30 C31 F15 1.7(2) . . . . ? C29 C30 C31 F15 -178.53(15) . . . . ? F14 C30 C31 C26 -178.68(15) . . . . ? C29 C30 C31 C26 1.1(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 74.49 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.322 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.054 _iucr_refine_instructions_details ; TITL eileen19a in P2(1)/c CELL 1.54184 9.5262 18.5035 17.6858 90.000 92.377 90.000 ZERR 4.00 0.0004 0.0008 0.0008 0.000 0.004 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H B N O F UNIT 124 96 4 16 4 60 SIZE 0.18 0.04 0.03 TEMP -173 SHEL 999 0.8 ACTA CONF FMAP 2 PLAN 10 L.S. 8 WGHT 0.059300 0.806200 FVAR 2.89586 B 3 0.469288 0.515568 0.740584 11.00000 0.02186 0.02389 = 0.02526 -0.00168 -0.00132 -0.00028 N1 4 0.789372 0.351293 0.583118 11.00000 0.01770 0.02261 = 0.02793 0.00026 0.00045 0.00040 N2 4 0.593818 0.305432 0.531826 11.00000 0.01695 0.02313 = 0.02591 0.00043 0.00000 0.00122 N3 4 0.580593 0.428931 0.577349 11.00000 0.02186 0.02563 = 0.02873 -0.00190 -0.00048 0.00010 N4 4 0.565942 0.437144 0.647249 11.00000 0.01998 0.02520 = 0.03152 -0.00155 0.00003 0.00026 O 5 0.493823 0.497484 0.658191 11.00000 0.02292 0.02364 = 0.02806 -0.00232 0.00123 0.00186 F1 6 0.613857 0.424536 0.866916 11.00000 0.02796 0.03196 = 0.04221 0.01324 -0.00226 -0.00331 F2 6 0.873366 0.442791 0.922459 11.00000 0.03153 0.03681 = 0.03907 0.00932 -0.00833 0.00276 F3 6 1.038568 0.550549 0.870934 11.00000 0.02318 0.03587 = 0.04855 0.00011 -0.00910 0.00026 F4 6 0.936886 0.638742 0.758175 11.00000 0.02505 0.03227 = 0.04660 0.00620 0.00007 -0.00600 F5 6 0.676498 0.621594 0.700409 11.00000 0.02549 0.03036 = 0.03121 0.00747 -0.00161 -0.00126 F6 6 0.510451 0.662104 0.821111 11.00000 0.02959 0.03054 = 0.02932 -0.00629 -0.00677 0.00115 F7 6 0.371357 0.782281 0.785705 11.00000 0.03864 0.02527 = 0.03626 -0.00742 0.00096 0.00118 F8 6 0.157012 0.781422 0.678735 11.00000 0.03859 0.03178 = 0.04176 -0.00015 -0.00172 0.01364 F9 6 0.084225 0.655097 0.608361 11.00000 0.02780 0.04264 = 0.03990 -0.00327 -0.01122 0.00689 F10 6 0.222695 0.533951 0.641623 11.00000 0.02710 0.02982 = 0.04249 -0.00808 -0.00819 -0.00048 F11 6 0.388314 0.530216 0.892798 11.00000 0.04049 0.03226 = 0.03226 -0.00806 0.00550 -0.00411 F12 6 0.227585 0.442115 0.972462 11.00000 0.04298 0.04937 = 0.03111 -0.00096 0.01087 -0.00193 F13 6 0.116786 0.320006 0.907634 11.00000 0.02818 0.04233 = 0.04362 0.01314 0.00421 -0.00507 F14 6 0.172328 0.288346 0.761238 11.00000 0.03192 0.02872 = 0.04645 0.00010 -0.00300 -0.00839 F15 6 0.326984 0.375499 0.680986 11.00000 0.03092 0.03211 = 0.02993 -0.00573 0.00030 -0.00479 C1 1 0.653426 0.364481 0.563818 11.00000 0.01808 0.02282 = 0.02624 0.00095 0.00186 0.00040 C2 1 0.813535 0.278101 0.568429 11.00000 0.02073 0.02282 = 0.03030 0.00001 0.00261 0.00154 C3 1 0.694015 0.250197 0.536548 11.00000 0.02079 0.02226 = 0.02786 0.00098 0.00240 0.00318 C4 1 0.898291 0.407374 0.608955 11.00000 0.01847 0.02330 = 0.03010 -0.00149 0.00053 -0.00334 C5 1 0.854911 0.483182 0.581472 11.00000 0.02650 0.02411 = 0.03888 0.00378 -0.00110 -0.00393 AFIX 137 H5A 2 0.777265 0.500781 0.611126 11.00000 -1.50000 H5B 2 0.824702 0.481023 0.527872 11.00000 -1.50000 H5C 2 0.935080 0.516121 0.587878 11.00000 -1.50000 AFIX 0 C6 1 0.914144 0.405170 0.694725 11.00000 0.02427 0.03261 = 0.03024 -0.00227 -0.00045 0.00027 AFIX 137 H6A 2 0.823329 0.415554 0.716440 11.00000 -1.50000 H6B 2 0.983081 0.441461 0.712153 11.00000 -1.50000 H6C 2 0.946251 0.357074 0.710927 11.00000 -1.50000 AFIX 0 C7 1 1.037512 0.389777 0.572379 11.00000 0.02091 0.03333 = 0.03375 -0.00379 0.00360 -0.00508 AFIX 137 H7A 2 1.101709 0.430922 0.578690 11.00000 -1.50000 H7B 2 1.019851 0.380153 0.518330 11.00000 -1.50000 H7C 2 1.079891 0.347018 0.596756 11.00000 -1.50000 AFIX 0 C8 1 0.944102 0.236493 0.589607 11.00000 0.02389 0.02593 = 0.05523 -0.00154 -0.00701 0.00315 AFIX 137 H8A 2 0.920639 0.185304 0.595626 11.00000 -1.50000 H8B 2 0.985389 0.255221 0.637358 11.00000 -1.50000 H8C 2 1.011744 0.241720 0.549701 11.00000 -1.50000 AFIX 0 C9 1 0.674662 0.173469 0.511350 11.00000 0.02603 0.02305 = 0.04159 -0.00351 -0.00257 0.00225 AFIX 137 H9A 2 0.695586 0.169406 0.457729 11.00000 -1.50000 H9B 2 0.577329 0.158624 0.518413 11.00000 -1.50000 H9C 2 0.738404 0.142153 0.541414 11.00000 -1.50000 AFIX 0 C10 1 0.446227 0.298931 0.495209 11.00000 0.01690 0.02624 = 0.02587 0.00021 -0.00242 -0.00155 C11 1 0.374529 0.372650 0.485736 11.00000 0.02080 0.02808 = 0.02961 0.00035 -0.00274 0.00267 AFIX 137 H11A 2 0.355377 0.392454 0.535656 11.00000 -1.50000 H11B 2 0.285979 0.366988 0.456111 11.00000 -1.50000 H11C 2 0.436355 0.405677 0.459380 11.00000 -1.50000 AFIX 0 C12 1 0.357213 0.250778 0.544753 11.00000 0.02022 0.03059 = 0.02914 0.00137 -0.00016 -0.00304 AFIX 137 H12A 2 0.398666 0.202344 0.547895 11.00000 -1.50000 H12B 2 0.261503 0.247567 0.522464 11.00000 -1.50000 H12C 2 0.354471 0.271591 0.595624 11.00000 -1.50000 AFIX 0 C13 1 0.460613 0.267831 0.415616 11.00000 0.02706 0.03048 = 0.02613 -0.00108 -0.00125 -0.00083 AFIX 137 H13A 2 0.524441 0.298231 0.387397 11.00000 -1.50000 H13B 2 0.368168 0.266720 0.389181 11.00000 -1.50000 H13C 2 0.498432 0.218648 0.419361 11.00000 -1.50000 AFIX 0 C14 1 0.627176 0.524235 0.782425 11.00000 0.02299 0.02410 = 0.02432 -0.00289 0.00141 0.00065 C15 1 0.686371 0.480532 0.838790 11.00000 0.02604 0.02490 = 0.02826 0.00067 0.00264 -0.00063 C16 1 0.822287 0.488150 0.869433 11.00000 0.02863 0.02848 = 0.02662 0.00118 -0.00253 0.00395 C17 1 0.906383 0.542211 0.842821 11.00000 0.02152 0.03053 = 0.03305 -0.00575 -0.00336 0.00166 C18 1 0.854518 0.586664 0.785623 11.00000 0.02441 0.02511 = 0.03151 -0.00083 0.00239 -0.00230 C19 1 0.719155 0.576703 0.757057 11.00000 0.02548 0.02451 = 0.02429 0.00022 0.00062 0.00230 C20 1 0.379864 0.591709 0.730601 11.00000 0.02179 0.02516 = 0.02389 -0.00162 0.00252 0.00072 C21 1 0.406534 0.656782 0.767283 11.00000 0.02117 0.02917 = 0.02335 -0.00094 0.00027 0.00056 C22 1 0.334051 0.720343 0.751136 11.00000 0.02662 0.02494 = 0.02762 -0.00390 0.00574 0.00028 C23 1 0.225476 0.720311 0.696614 11.00000 0.02597 0.02722 = 0.03121 0.00201 0.00479 0.00696 C24 1 0.191043 0.656393 0.660632 11.00000 0.02077 0.03443 = 0.02769 -0.00026 -0.00112 0.00285 C25 1 0.266170 0.594643 0.678344 11.00000 0.02252 0.02579 = 0.03108 -0.00460 0.00131 -0.00026 C26 1 0.368599 0.457530 0.783270 11.00000 0.01990 0.02599 = 0.02931 0.00064 -0.00014 0.00196 C27 1 0.335191 0.470789 0.857807 11.00000 0.02574 0.02597 = 0.03262 -0.00192 0.00151 0.00106 C28 1 0.252574 0.426412 0.900376 11.00000 0.02558 0.03554 = 0.02970 0.00171 0.00318 0.00409 C29 1 0.196529 0.364550 0.867627 11.00000 0.02066 0.03255 = 0.03816 0.01048 0.00097 0.00055 C30 1 0.225010 0.348800 0.793809 11.00000 0.02163 0.02524 = 0.03809 0.00239 -0.00478 -0.00003 C31 1 0.308339 0.395093 0.753256 11.00000 0.02047 0.02727 = 0.02834 -0.00009 -0.00071 0.00105 HKLF 4 ; _database_code_depnum_ccdc_archive 'CCDC 963626' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_dhol26 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H20 B F15 N2 O2' _chemical_formula_weight 736.29 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' B B 0.0013 0.0007 '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 monoclinic _symmetry_space_group_name_H-M 'P 21/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 16.7931(8) _cell_length_b 10.2527(4) _cell_length_c 17.3649(8) _cell_angle_alpha 90.00 _cell_angle_beta 101.923(4) _cell_angle_gamma 90.00 _cell_volume 2925.3(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 11578 _cell_measurement_theta_min 2.7354 _cell_measurement_theta_max 30.6805 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.672 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1480 _exptl_absorpt_coefficient_mu 0.170 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.83820 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur S' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean 16.1057 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 39003 _diffrn_reflns_av_R_equivalents 0.0510 _diffrn_reflns_av_sigmaI/netI 0.0631 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.74 _diffrn_reflns_theta_max 28.28 _reflns_number_total 7238 _reflns_number_gt 4334 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Siemens XP' _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. One tert-Butyl group (C10 C11 C12 atoms) is disordered over two positions. Several restraints (SADI, SAME and SIMU) were used in order to improve refinement stability. ; _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^)+(0.0457P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7238 _refine_ls_number_parameters 485 _refine_ls_number_restraints 21 _refine_ls_R_factor_all 0.0836 _refine_ls_R_factor_gt 0.0397 _refine_ls_wR_factor_ref 0.0878 _refine_ls_wR_factor_gt 0.0808 _refine_ls_goodness_of_fit_ref 0.917 _refine_ls_restrained_S_all 0.916 _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 B B 0.51458(11) 0.64952(17) 0.25845(10) 0.0163(4) Uani 1 1 d . . . O1 O 0.45100(6) 0.58870(11) 0.19188(6) 0.0214(3) Uani 1 1 d . . . O2 O 0.52275(7) 0.50086(13) 0.10753(7) 0.0374(3) Uani 1 1 d . . . N1 N 0.32707(8) 0.55183(12) 0.03102(7) 0.0196(3) Uani 1 1 d . . . N2 N 0.34992(8) 0.35847(12) 0.08381(7) 0.0201(3) Uani 1 1 d . A . F1 F 0.38650(7) 0.49976(12) 0.30690(7) 0.0490(3) Uani 1 1 d . . . F2 F 0.39916(10) 0.33611(13) 0.42549(8) 0.0773(5) Uani 1 1 d . . . F3 F 0.54649(11) 0.29120(11) 0.52312(7) 0.0770(5) Uani 1 1 d . . . F4 F 0.67774(8) 0.42624(11) 0.50104(6) 0.0514(4) Uani 1 1 d . . . F5 F 0.66725(6) 0.59074(9) 0.38266(5) 0.0265(2) Uani 1 1 d . . . F6 F 0.65222(5) 0.47474(8) 0.24692(5) 0.0190(2) Uani 1 1 d . . . F7 F 0.78645(5) 0.53926(9) 0.19717(5) 0.0264(2) Uani 1 1 d . . . F8 F 0.80175(6) 0.77731(10) 0.13529(6) 0.0321(3) Uani 1 1 d . . . F9 F 0.67957(6) 0.95676(9) 0.12841(6) 0.0325(3) Uani 1 1 d . . . F10 F 0.54919(6) 0.90095(9) 0.18509(5) 0.0253(2) Uani 1 1 d . . . F11 F 0.60053(6) 0.84059(9) 0.36550(5) 0.0274(2) Uani 1 1 d . . . F12 F 0.54095(7) 1.03916(10) 0.43265(7) 0.0491(3) Uani 1 1 d . . . F13 F 0.37737(8) 1.08577(11) 0.40100(8) 0.0607(4) Uani 1 1 d . . . F14 F 0.27751(7) 0.93284(13) 0.29680(7) 0.0552(4) Uani 1 1 d . . . F15 F 0.33458(6) 0.73516(12) 0.22727(6) 0.0428(3) Uani 1 1 d . . . C1 C 0.38013(10) 0.47979(15) 0.08218(9) 0.0184(3) Uani 1 1 d . . . C2 C 0.26106(10) 0.47419(16) 0.00080(9) 0.0221(4) Uani 1 1 d . . . H2 H 0.2139 0.5003 -0.0362 0.026 Uiso 1 1 calc R . . C3 C 0.27506(10) 0.35578(16) 0.03271(9) 0.0225(4) Uani 1 1 d . . . H3 H 0.2398 0.2826 0.0221 0.027 Uiso 1 1 calc R . . C4 C 0.33078(10) 0.69308(15) 0.00514(10) 0.0218(4) Uani 1 1 d . . . C6 C 0.41279(12) 0.75388(19) 0.03834(13) 0.0455(6) Uani 1 1 d . . . H6A H 0.4199 0.7622 0.0956 0.068 Uiso 1 1 calc R . . H6B H 0.4156 0.8404 0.0150 0.068 Uiso 1 1 calc R . . H6C H 0.4560 0.6984 0.0259 0.068 Uiso 1 1 calc R . . C7 C 0.26371(12) 0.76510(17) 0.03412(10) 0.0318(4) Uani 1 1 d . . . H7A H 0.2108 0.7277 0.0096 0.048 Uiso 1 1 calc R . . H7B H 0.2649 0.8576 0.0201 0.048 Uiso 1 1 calc R . . H7C H 0.2720 0.7565 0.0914 0.048 Uiso 1 1 calc R . . C5 C 0.31569(10) 0.69279(16) -0.08449(9) 0.0241(4) Uani 1 1 d . . . H5A H 0.3558 0.6364 -0.1017 0.036 Uiso 1 1 calc R . . H5B H 0.3208 0.7818 -0.1034 0.036 Uiso 1 1 calc R . . H5C H 0.2608 0.6599 -0.1059 0.036 Uiso 1 1 calc R . . C8 C 0.38738(10) 0.23677(15) 0.12645(9) 0.0240(4) Uani 1 1 d D . . C9 C 0.3278(2) 0.1943(3) 0.1768(2) 0.0392(10) Uani 0.596(4) 1 d PD A 1 H9A H 0.3250 0.2615 0.2164 0.059 Uiso 0.596(4) 1 calc PR A 1 H9B H 0.3462 0.1120 0.2032 0.059 Uiso 0.596(4) 1 calc PR A 1 H9C H 0.2737 0.1822 0.1433 0.059 Uiso 0.596(4) 1 calc PR A 1 C10 C 0.3941(2) 0.1361(3) 0.06422(18) 0.0299(9) Uani 0.596(4) 1 d PD A 1 H10A H 0.3397 0.1166 0.0331 0.045 Uiso 0.596(4) 1 calc PR A 1 H10B H 0.4185 0.0562 0.0897 0.045 Uiso 0.596(4) 1 calc PR A 1 H10C H 0.4284 0.1704 0.0296 0.045 Uiso 0.596(4) 1 calc PR A 1 C11 C 0.4710(2) 0.2614(3) 0.1782(2) 0.0346(9) Uani 0.596(4) 1 d PD A 1 H11A H 0.5089 0.2884 0.1453 0.052 Uiso 0.596(4) 1 calc PR A 1 H11B H 0.4909 0.1811 0.2064 0.052 Uiso 0.596(4) 1 calc PR A 1 H11C H 0.4669 0.3304 0.2163 0.052 Uiso 0.596(4) 1 calc PR A 1 C9' C 0.3234(3) 0.1299(5) 0.1258(3) 0.0383(14) Uani 0.404(4) 1 d PD A 2 H9D H 0.3008 0.1038 0.0714 0.057 Uiso 0.404(4) 1 calc PR A 2 H9E H 0.2797 0.1633 0.1500 0.057 Uiso 0.404(4) 1 calc PR A 2 H9F H 0.3488 0.0543 0.1556 0.057 Uiso 0.404(4) 1 calc PR A 2 C10' C 0.4500(3) 0.1894(5) 0.0805(3) 0.0319(13) Uani 0.404(4) 1 d PD A 2 H10D H 0.4753 0.1089 0.1043 0.048 Uiso 0.404(4) 1 calc PR A 2 H10E H 0.4919 0.2564 0.0818 0.048 Uiso 0.404(4) 1 calc PR A 2 H10F H 0.4230 0.1725 0.0258 0.048 Uiso 0.404(4) 1 calc PR A 2 C11' C 0.4273(3) 0.2657(4) 0.2117(3) 0.0288(12) Uani 0.404(4) 1 d PD A 2 H11D H 0.4502 0.1851 0.2376 0.043 Uiso 0.404(4) 1 calc PR A 2 H11E H 0.3865 0.3007 0.2392 0.043 Uiso 0.404(4) 1 calc PR A 2 H11F H 0.4708 0.3299 0.2133 0.043 Uiso 0.404(4) 1 calc PR A 2 C12 C 0.46132(10) 0.52550(15) 0.12997(10) 0.0210(4) Uani 1 1 d . . . C13 C 0.52752(10) 0.54714(15) 0.33285(9) 0.0191(4) Uani 1 1 d . . . C14 C 0.46164(12) 0.48042(17) 0.35040(11) 0.0312(4) Uani 1 1 d . . . C15 C 0.46680(15) 0.39407(18) 0.41235(13) 0.0457(6) Uani 1 1 d . . . C16 C 0.54028(17) 0.37352(18) 0.46218(11) 0.0456(6) Uani 1 1 d . . . C17 C 0.60560(13) 0.44185(17) 0.45043(10) 0.0344(5) Uani 1 1 d . . . C18 C 0.59895(11) 0.52659(16) 0.38783(9) 0.0225(4) Uani 1 1 d . . . C19 C 0.59572(9) 0.68692(14) 0.22457(8) 0.0146(3) Uani 1 1 d . . . C20 C 0.65806(10) 0.59896(15) 0.22270(9) 0.0164(3) Uani 1 1 d . . . C21 C 0.72725(10) 0.62822(15) 0.19526(9) 0.0190(4) Uani 1 1 d . . . C22 C 0.73512(10) 0.74944(17) 0.16393(9) 0.0221(4) Uani 1 1 d . . . C23 C 0.67410(10) 0.83880(15) 0.16068(9) 0.0215(4) Uani 1 1 d . . . C24 C 0.60686(10) 0.80628(15) 0.19117(9) 0.0184(4) Uani 1 1 d . . . C25 C 0.47195(10) 0.77729(15) 0.29132(9) 0.0179(3) Uani 1 1 d . . . C26 C 0.51911(10) 0.86012(15) 0.34519(9) 0.0202(4) Uani 1 1 d . . . C27 C 0.48963(12) 0.96302(16) 0.38150(10) 0.0289(4) Uani 1 1 d . . . C28 C 0.40803(13) 0.98661(17) 0.36584(11) 0.0352(5) Uani 1 1 d . . . C29 C 0.35782(12) 0.90878(19) 0.31338(11) 0.0337(5) Uani 1 1 d . . . C30 C 0.38964(10) 0.80665(17) 0.27760(9) 0.0256(4) 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 B 0.0119(10) 0.0185(9) 0.0172(9) -0.0028(7) 0.0001(7) -0.0023(7) O1 0.0155(6) 0.0259(6) 0.0222(6) -0.0075(5) 0.0024(5) -0.0037(5) O2 0.0183(7) 0.0485(8) 0.0421(8) -0.0265(6) -0.0016(6) 0.0068(6) N1 0.0168(8) 0.0177(7) 0.0219(7) -0.0008(6) -0.0018(6) -0.0018(6) N2 0.0208(8) 0.0162(7) 0.0209(7) -0.0033(6) -0.0014(6) -0.0010(6) F1 0.0300(7) 0.0600(8) 0.0621(8) -0.0057(6) 0.0211(6) -0.0211(6) F2 0.1182(13) 0.0518(8) 0.0861(10) -0.0139(7) 0.0775(10) -0.0468(8) F3 0.1824(16) 0.0241(6) 0.0390(7) 0.0106(5) 0.0567(9) 0.0040(8) F4 0.0915(10) 0.0385(7) 0.0201(5) 0.0052(5) 0.0021(6) 0.0352(6) F5 0.0236(6) 0.0340(6) 0.0198(5) -0.0016(4) -0.0004(4) 0.0056(4) F6 0.0201(5) 0.0162(5) 0.0219(5) 0.0011(4) 0.0067(4) 0.0011(4) F7 0.0196(5) 0.0318(6) 0.0301(5) -0.0041(4) 0.0104(4) 0.0026(4) F8 0.0315(6) 0.0364(6) 0.0338(6) -0.0074(5) 0.0196(5) -0.0153(5) F9 0.0455(7) 0.0217(5) 0.0330(6) 0.0065(4) 0.0141(5) -0.0100(5) F10 0.0287(6) 0.0176(5) 0.0294(5) 0.0055(4) 0.0055(4) 0.0031(4) F11 0.0226(6) 0.0305(6) 0.0280(5) -0.0103(4) 0.0028(4) -0.0049(4) F12 0.0672(9) 0.0335(6) 0.0536(7) -0.0266(6) 0.0287(6) -0.0166(6) F13 0.0825(10) 0.0345(7) 0.0790(9) -0.0088(6) 0.0491(8) 0.0196(6) F14 0.0369(7) 0.0814(9) 0.0501(7) 0.0085(7) 0.0152(6) 0.0363(7) F15 0.0168(6) 0.0774(8) 0.0317(6) -0.0158(6) -0.0011(5) 0.0075(5) C1 0.0173(9) 0.0166(8) 0.0199(8) -0.0035(7) 0.0006(7) 0.0016(7) C2 0.0142(9) 0.0266(9) 0.0223(8) -0.0021(7) -0.0034(7) -0.0039(7) C3 0.0201(10) 0.0236(9) 0.0215(8) -0.0029(7) -0.0011(7) -0.0060(7) C4 0.0222(10) 0.0158(8) 0.0246(9) 0.0015(7) -0.0013(7) 0.0004(7) C6 0.0408(13) 0.0260(10) 0.0578(14) 0.0142(10) -0.0177(10) -0.0168(9) C7 0.0507(13) 0.0236(9) 0.0218(9) -0.0018(8) 0.0087(9) 0.0079(9) C5 0.0225(10) 0.0239(9) 0.0274(9) 0.0001(7) 0.0088(8) 0.0012(7) C8 0.0294(11) 0.0162(8) 0.0242(9) 0.0010(7) 0.0007(8) 0.0024(7) C9 0.049(2) 0.033(2) 0.038(2) 0.0153(17) 0.0151(18) 0.0105(16) C10 0.028(2) 0.0197(16) 0.0407(19) -0.0073(14) 0.0035(15) 0.0005(14) C11 0.043(2) 0.0198(16) 0.035(2) -0.0010(14) -0.0062(17) 0.0077(15) C9' 0.049(3) 0.021(3) 0.043(3) 0.002(2) 0.006(3) -0.004(2) C10' 0.035(3) 0.026(3) 0.034(3) -0.002(2) 0.006(2) 0.007(2) C11' 0.039(3) 0.017(2) 0.028(3) 0.0025(19) 0.001(2) 0.000(2) C12 0.0187(10) 0.0161(8) 0.0256(9) -0.0042(7) -0.0012(7) 0.0022(7) C13 0.0255(10) 0.0127(8) 0.0222(8) -0.0019(6) 0.0119(7) -0.0003(7) C14 0.0340(12) 0.0281(10) 0.0366(10) -0.0059(8) 0.0187(9) -0.0082(8) C15 0.0801(18) 0.0226(10) 0.0509(13) -0.0090(10) 0.0522(14) -0.0196(11) C16 0.102(2) 0.0173(10) 0.0271(11) 0.0038(8) 0.0343(13) 0.0035(11) C17 0.0627(15) 0.0224(10) 0.0197(9) 0.0008(7) 0.0120(9) 0.0177(9) C18 0.0318(11) 0.0190(9) 0.0191(8) 0.0001(7) 0.0111(8) 0.0062(7) C19 0.0151(9) 0.0164(8) 0.0112(7) -0.0019(6) 0.0002(6) -0.0028(6) C20 0.0184(9) 0.0161(8) 0.0139(7) -0.0014(6) 0.0016(7) -0.0047(6) C21 0.0162(9) 0.0224(9) 0.0187(8) -0.0059(7) 0.0040(7) 0.0004(7) C22 0.0207(10) 0.0286(10) 0.0196(8) -0.0065(7) 0.0103(7) -0.0121(8) C23 0.0300(11) 0.0167(8) 0.0178(8) 0.0022(7) 0.0051(7) -0.0109(7) C24 0.0186(9) 0.0183(8) 0.0168(8) -0.0024(6) 0.0001(7) -0.0001(7) C25 0.0194(9) 0.0186(8) 0.0158(8) 0.0021(6) 0.0036(7) 0.0024(7) C26 0.0231(10) 0.0180(8) 0.0207(8) 0.0021(7) 0.0071(7) 0.0006(7) C27 0.0440(13) 0.0178(9) 0.0293(10) -0.0045(7) 0.0174(9) -0.0051(8) C28 0.0545(14) 0.0220(10) 0.0366(11) 0.0014(8) 0.0266(10) 0.0140(9) C29 0.0296(11) 0.0451(12) 0.0292(10) 0.0117(9) 0.0129(9) 0.0219(9) C30 0.0205(10) 0.0385(11) 0.0161(8) 0.0022(8) 0.0001(7) 0.0053(8) _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 B O1 1.535(2) . ? B C19 1.637(2) . ? B C13 1.644(2) . ? B C25 1.650(2) . ? O1 C12 1.2972(19) . ? O2 C12 1.2024(19) . ? N1 C1 1.342(2) . ? N1 C2 1.377(2) . ? N1 C4 1.521(2) . ? N2 C1 1.346(2) . ? N2 C3 1.381(2) . ? N2 C8 1.519(2) . ? F1 C14 1.345(2) . ? F2 C15 1.342(2) . ? F3 C16 1.341(2) . ? F4 C17 1.351(2) . ? F5 C18 1.3412(19) . ? F6 C20 1.3512(17) . ? F7 C21 1.3445(18) . ? F8 C22 1.3456(17) . ? F9 C23 1.3440(17) . ? F10 C24 1.3598(18) . ? F11 C26 1.3546(18) . ? F12 C27 1.351(2) . ? F13 C28 1.342(2) . ? F14 C29 1.342(2) . ? F15 C30 1.3498(19) . ? C1 C12 1.516(2) . ? C2 C3 1.335(2) . ? C4 C6 1.513(2) . ? C4 C7 1.517(2) . ? C4 C5 1.524(2) . ? C8 C10 1.515(3) . ? C8 C9 1.523(3) . ? C8 C11' 1.523(4) . ? C8 C11 1.523(3) . ? C8 C10' 1.525(5) . ? C8 C9' 1.533(5) . ? C13 C18 1.386(2) . ? C13 C14 1.387(2) . ? C14 C15 1.382(3) . ? C15 C16 1.369(3) . ? C16 C17 1.352(3) . ? C17 C18 1.378(2) . ? C19 C24 1.383(2) . ? C19 C20 1.387(2) . ? C20 C21 1.377(2) . ? C21 C22 1.374(2) . ? C22 C23 1.367(2) . ? C23 C24 1.383(2) . ? C25 C26 1.385(2) . ? C25 C30 1.386(2) . ? C26 C27 1.373(2) . ? C27 C28 1.362(3) . ? C28 C29 1.364(3) . ? C29 C30 1.380(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 B C19 109.00(12) . . ? O1 B C13 106.92(12) . . ? C19 B C13 116.56(13) . . ? O1 B C25 107.40(12) . . ? C19 B C25 113.02(13) . . ? C13 B C25 103.38(12) . . ? C12 O1 B 129.49(13) . . ? C1 N1 C2 107.83(13) . . ? C1 N1 C4 131.09(13) . . ? C2 N1 C4 121.08(13) . . ? C1 N2 C3 107.58(13) . . ? C1 N2 C8 130.49(13) . . ? C3 N2 C8 121.80(13) . . ? N1 C1 N2 108.71(13) . . ? N1 C1 C12 126.23(14) . . ? N2 C1 C12 125.05(14) . . ? C3 C2 N1 107.97(14) . . ? C2 C3 N2 107.90(14) . . ? C6 C4 C7 110.66(15) . . ? C6 C4 N1 111.66(13) . . ? C7 C4 N1 106.67(13) . . ? C6 C4 C5 109.63(15) . . ? C7 C4 C5 111.20(13) . . ? N1 C4 C5 106.94(12) . . ? C10 C8 N2 107.23(16) . . ? C10 C8 C9 111.7(2) . . ? N2 C8 C9 105.04(17) . . ? C10 C8 C11' 138.0(2) . . ? N2 C8 C11' 111.6(2) . . ? C9 C8 C11' 72.9(3) . . ? C10 C8 C11 109.8(2) . . ? N2 C8 C11 112.95(16) . . ? C9 C8 C11 110.1(2) . . ? C11' C8 C11 39.4(2) . . ? C10 C8 C10' 41.3(2) . . ? N2 C8 C10' 105.5(2) . . ? C9 C8 C10' 144.7(3) . . ? C11' C8 C10' 111.0(3) . . ? C11 C8 C10' 73.2(2) . . ? C10 C8 C9' 70.3(2) . . ? N2 C8 C9' 111.4(2) . . ? C9 C8 C9' 42.0(2) . . ? C11' C8 C9' 108.3(3) . . ? C11 C8 C9' 133.0(2) . . ? C10' C8 C9' 109.0(3) . . ? O2 C12 O1 130.09(15) . . ? O2 C12 C1 119.49(14) . . ? O1 C12 C1 110.42(14) . . ? C18 C13 C14 112.94(15) . . ? C18 C13 B 126.40(14) . . ? C14 C13 B 120.37(15) . . ? F1 C14 C15 115.62(17) . . ? F1 C14 C13 120.16(16) . . ? C15 C14 C13 124.21(19) . . ? F2 C15 C16 120.5(2) . . ? F2 C15 C14 119.8(2) . . ? C16 C15 C14 119.60(18) . . ? F3 C16 C17 120.8(2) . . ? F3 C16 C15 120.6(2) . . ? C17 C16 C15 118.57(17) . . ? F4 C17 C16 119.13(17) . . ? F4 C17 C18 120.22(18) . . ? C16 C17 C18 120.64(19) . . ? F5 C18 C17 115.53(16) . . ? F5 C18 C13 120.64(14) . . ? C17 C18 C13 123.83(17) . . ? C24 C19 C20 113.40(14) . . ? C24 C19 B 123.53(14) . . ? C20 C19 B 122.98(13) . . ? F6 C20 C21 115.71(14) . . ? F6 C20 C19 120.12(13) . . ? C21 C20 C19 124.15(14) . . ? F7 C21 C22 119.48(14) . . ? F7 C21 C20 121.08(14) . . ? C22 C21 C20 119.42(15) . . ? F8 C22 C23 121.05(15) . . ? F8 C22 C21 119.60(15) . . ? C23 C22 C21 119.33(15) . . ? F9 C23 C22 120.34(14) . . ? F9 C23 C24 120.52(15) . . ? C22 C23 C24 119.14(15) . . ? F10 C24 C23 115.02(14) . . ? F10 C24 C19 120.54(14) . . ? C23 C24 C19 124.43(15) . . ? C26 C25 C30 113.19(15) . . ? C26 C25 B 119.47(14) . . ? C30 C25 B 126.96(14) . . ? F11 C26 C27 115.74(15) . . ? F11 C26 C25 119.41(14) . . ? C27 C26 C25 124.85(16) . . ? F12 C27 C28 120.50(16) . . ? F12 C27 C26 120.30(17) . . ? C28 C27 C26 119.21(17) . . ? F13 C28 C27 120.54(18) . . ? F13 C28 C29 120.32(19) . . ? C27 C28 C29 119.14(16) . . ? F14 C29 C28 119.39(17) . . ? F14 C29 C30 120.53(18) . . ? C28 C29 C30 120.08(17) . . ? F15 C30 C29 115.24(16) . . ? F15 C30 C25 121.25(15) . . ? C29 C30 C25 123.52(16) . . ? 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 C19 B O1 C12 26.8(2) . . . . ? C13 B O1 C12 -100.05(17) . . . . ? C25 B O1 C12 149.54(15) . . . . ? C2 N1 C1 N2 1.11(18) . . . . ? C4 N1 C1 N2 -178.72(14) . . . . ? C2 N1 C1 C12 -179.54(15) . . . . ? C4 N1 C1 C12 0.6(3) . . . . ? C3 N2 C1 N1 -0.84(17) . . . . ? C8 N2 C1 N1 174.96(14) . . . . ? C3 N2 C1 C12 179.80(15) . . . . ? C8 N2 C1 C12 -4.4(3) . . . . ? C1 N1 C2 C3 -0.96(18) . . . . ? C4 N1 C2 C3 178.89(14) . . . . ? N1 C2 C3 N2 0.44(19) . . . . ? C1 N2 C3 C2 0.24(18) . . . . ? C8 N2 C3 C2 -176.01(14) . . . . ? C1 N1 C4 C6 6.8(2) . . . . ? C2 N1 C4 C6 -173.06(16) . . . . ? C1 N1 C4 C7 -114.25(18) . . . . ? C2 N1 C4 C7 65.93(18) . . . . ? C1 N1 C4 C5 126.68(17) . . . . ? C2 N1 C4 C5 -53.13(19) . . . . ? C1 N2 C8 C10 -117.8(2) . . . . ? C3 N2 C8 C10 57.5(2) . . . . ? C1 N2 C8 C9 123.3(2) . . . . ? C3 N2 C8 C9 -61.4(2) . . . . ? C1 N2 C8 C11' 46.0(3) . . . . ? C3 N2 C8 C11' -138.7(3) . . . . ? C1 N2 C8 C11 3.3(3) . . . . ? C3 N2 C8 C11 178.6(2) . . . . ? C1 N2 C8 C10' -74.7(3) . . . . ? C3 N2 C8 C10' 100.6(3) . . . . ? C1 N2 C8 C9' 167.2(3) . . . . ? C3 N2 C8 C9' -17.5(3) . . . . ? B O1 C12 O2 -2.1(3) . . . . ? B O1 C12 C1 178.07(13) . . . . ? N1 C1 C12 O2 -98.8(2) . . . . ? N2 C1 C12 O2 80.5(2) . . . . ? N1 C1 C12 O1 81.1(2) . . . . ? N2 C1 C12 O1 -99.63(18) . . . . ? O1 B C13 C18 147.95(15) . . . . ? C19 B C13 C18 25.8(2) . . . . ? C25 B C13 C18 -98.86(17) . . . . ? O1 B C13 C14 -38.68(19) . . . . ? C19 B C13 C14 -160.85(14) . . . . ? C25 B C13 C14 74.51(17) . . . . ? C18 C13 C14 F1 173.75(15) . . . . ? B C13 C14 F1 -0.5(2) . . . . ? C18 C13 C14 C15 -4.9(2) . . . . ? B C13 C14 C15 -179.10(16) . . . . ? F1 C14 C15 F2 0.0(3) . . . . ? C13 C14 C15 F2 178.68(16) . . . . ? F1 C14 C15 C16 -176.69(16) . . . . ? C13 C14 C15 C16 2.0(3) . . . . ? F2 C15 C16 F3 2.7(3) . . . . ? C14 C15 C16 F3 179.31(16) . . . . ? F2 C15 C16 C17 -174.75(16) . . . . ? C14 C15 C16 C17 1.9(3) . . . . ? F3 C16 C17 F4 0.0(3) . . . . ? C15 C16 C17 F4 177.42(16) . . . . ? F3 C16 C17 C18 -179.85(15) . . . . ? C15 C16 C17 C18 -2.5(3) . . . . ? F4 C17 C18 F5 -0.9(2) . . . . ? C16 C17 C18 F5 178.95(15) . . . . ? F4 C17 C18 C13 179.28(14) . . . . ? C16 C17 C18 C13 -0.8(3) . . . . ? C14 C13 C18 F5 -175.47(14) . . . . ? B C13 C18 F5 -1.7(2) . . . . ? C14 C13 C18 C17 4.3(2) . . . . ? B C13 C18 C17 178.10(15) . . . . ? O1 B C19 C24 89.78(17) . . . . ? C13 B C19 C24 -149.14(14) . . . . ? C25 B C19 C24 -29.6(2) . . . . ? O1 B C19 C20 -86.52(17) . . . . ? C13 B C19 C20 34.6(2) . . . . ? C25 B C19 C20 154.13(14) . . . . ? C24 C19 C20 F6 -174.23(13) . . . . ? B C19 C20 F6 2.4(2) . . . . ? C24 C19 C20 C21 4.0(2) . . . . ? B C19 C20 C21 -179.34(14) . . . . ? F6 C20 C21 F7 -3.6(2) . . . . ? C19 C20 C21 F7 178.11(14) . . . . ? F6 C20 C21 C22 175.06(13) . . . . ? C19 C20 C21 C22 -3.3(2) . . . . ? F7 C21 C22 F8 0.3(2) . . . . ? C20 C21 C22 F8 -178.37(13) . . . . ? F7 C21 C22 C23 178.74(14) . . . . ? C20 C21 C22 C23 0.1(2) . . . . ? F8 C22 C23 F9 0.2(2) . . . . ? C21 C22 C23 F9 -178.27(14) . . . . ? F8 C22 C23 C24 -179.69(14) . . . . ? C21 C22 C23 C24 1.9(2) . . . . ? F9 C23 C24 F10 0.4(2) . . . . ? C22 C23 C24 F10 -179.77(14) . . . . ? F9 C23 C24 C19 179.23(14) . . . . ? C22 C23 C24 C19 -0.9(2) . . . . ? C20 C19 C24 F10 176.88(13) . . . . ? B C19 C24 F10 0.3(2) . . . . ? C20 C19 C24 C23 -1.9(2) . . . . ? B C19 C24 C23 -178.54(14) . . . . ? O1 B C25 C26 -172.05(13) . . . . ? C19 B C25 C26 -51.79(19) . . . . ? C13 B C25 C26 75.12(17) . . . . ? O1 B C25 C30 15.5(2) . . . . ? C19 B C25 C30 135.71(16) . . . . ? C13 B C25 C30 -97.38(18) . . . . ? C30 C25 C26 F11 178.45(13) . . . . ? B C25 C26 F11 5.0(2) . . . . ? C30 C25 C26 C27 -1.0(2) . . . . ? B C25 C26 C27 -174.47(15) . . . . ? F11 C26 C27 F12 1.3(2) . . . . ? C25 C26 C27 F12 -179.24(15) . . . . ? F11 C26 C27 C28 -178.12(15) . . . . ? C25 C26 C27 C28 1.3(3) . . . . ? F12 C27 C28 F13 0.0(3) . . . . ? C26 C27 C28 F13 179.39(15) . . . . ? F12 C27 C28 C29 179.41(16) . . . . ? C26 C27 C28 C29 -1.2(3) . . . . ? F13 C28 C29 F14 0.5(3) . . . . ? C27 C28 C29 F14 -178.96(16) . . . . ? F13 C28 C29 C30 -179.77(16) . . . . ? C27 C28 C29 C30 0.8(3) . . . . ? F14 C29 C30 F15 -0.8(2) . . . . ? C28 C29 C30 F15 179.43(16) . . . . ? F14 C29 C30 C25 179.24(15) . . . . ? C28 C29 C30 C25 -0.5(3) . . . . ? C26 C25 C30 F15 -179.38(14) . . . . ? B C25 C30 F15 -6.5(3) . . . . ? C26 C25 C30 C29 0.6(2) . . . . ? B C25 C30 C29 173.46(16) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.294 _refine_diff_density_min -0.448 _refine_diff_density_rms 0.048 _iucr_refine_instructions_details ; TITL dhol26 in P2(1)/n CELL 0.71073 16.7931 10.2527 17.3649 90.000 101.923 90.000 ZERR 4.00 0.0008 0.0004 0.0008 0.000 0.004 0.000 LATT 1 SYMM 1/2 - X, 1/2 + Y, 1/2 - Z SFAC C H B N O F UNIT 120 80 4 8 8 60 SIZE 0.18 0.16 0.10 TEMP -173 SHEL 999 0.75 ACTA CONF FMAP 2 PLAN 10 L.S. 4 OMIT -5 3 3 OMIT 4 4 4 OMIT 3 3 5 OMIT -7 0 5 WGHT 0.045700 FVAR 3.00750 0.59553 B 3 0.514580 0.649523 0.258453 11.00000 0.01185 0.01849 = 0.01725 -0.00276 0.00012 -0.00233 O1 5 0.451004 0.588698 0.191883 11.00000 0.01553 0.02585 = 0.02219 -0.00752 0.00237 -0.00373 O2 5 0.522752 0.500865 0.107526 11.00000 0.01826 0.04847 = 0.04209 -0.02647 -0.00159 0.00680 N1 4 0.327071 0.551828 0.031020 11.00000 0.01676 0.01767 = 0.02188 -0.00076 -0.00182 -0.00184 N2 4 0.349922 0.358467 0.083807 11.00000 0.02078 0.01624 = 0.02088 -0.00328 -0.00140 -0.00102 F1 6 0.386498 0.499762 0.306901 11.00000 0.02998 0.05998 = 0.06209 -0.00570 0.02109 -0.02106 F2 6 0.399164 0.336105 0.425487 11.00000 0.11825 0.05176 = 0.08610 -0.01395 0.07751 -0.04683 F3 6 0.546489 0.291196 0.523122 11.00000 0.18242 0.02413 = 0.03900 0.01061 0.05669 0.00396 F4 6 0.677740 0.426243 0.501039 11.00000 0.09151 0.03847 = 0.02009 0.00518 0.00209 0.03523 F5 6 0.667254 0.590740 0.382656 11.00000 0.02359 0.03402 = 0.01982 -0.00155 -0.00038 0.00557 F6 6 0.652218 0.474737 0.246915 11.00000 0.02012 0.01615 = 0.02188 0.00109 0.00674 0.00112 F7 6 0.786449 0.539264 0.197171 11.00000 0.01956 0.03177 = 0.03011 -0.00408 0.01041 0.00256 F8 6 0.801749 0.777313 0.135288 11.00000 0.03155 0.03641 = 0.03385 -0.00740 0.01961 -0.01531 F9 6 0.679573 0.956757 0.128413 11.00000 0.04546 0.02173 = 0.03296 0.00651 0.01406 -0.00999 F10 6 0.549187 0.900948 0.185086 11.00000 0.02871 0.01764 = 0.02939 0.00550 0.00548 0.00306 F11 6 0.600530 0.840592 0.365503 11.00000 0.02261 0.03050 = 0.02798 -0.01027 0.00276 -0.00491 F12 6 0.540955 1.039156 0.432650 11.00000 0.06722 0.03347 = 0.05359 -0.02657 0.02869 -0.01657 F13 6 0.377372 1.085766 0.400996 11.00000 0.08253 0.03452 = 0.07897 -0.00879 0.04905 0.01957 F14 6 0.277512 0.932838 0.296800 11.00000 0.03685 0.08139 = 0.05011 0.00855 0.01518 0.03627 F15 6 0.334576 0.735159 0.227274 11.00000 0.01678 0.07735 = 0.03170 -0.01578 -0.00112 0.00747 C1 1 0.380134 0.479789 0.082179 11.00000 0.01725 0.01660 = 0.01993 -0.00352 0.00057 0.00161 C2 1 0.261063 0.474192 0.000796 11.00000 0.01418 0.02662 = 0.02233 -0.00208 -0.00340 -0.00389 AFIX 43 H2 2 0.213883 0.500310 -0.036241 11.00000 -1.20000 AFIX 0 C3 1 0.275057 0.355781 0.032710 11.00000 0.02014 0.02356 = 0.02150 -0.00294 -0.00115 -0.00603 AFIX 43 H3 2 0.239768 0.282624 0.022144 11.00000 -1.20000 AFIX 0 C4 1 0.330775 0.693079 0.005138 11.00000 0.02223 0.01579 = 0.02462 0.00152 -0.00134 0.00040 C6 1 0.412795 0.753878 0.038340 11.00000 0.04081 0.02596 = 0.05782 0.01424 -0.01768 -0.01685 AFIX 137 H6A 2 0.419930 0.762227 0.095578 11.00000 -1.50000 H6B 2 0.415613 0.840386 0.015047 11.00000 -1.50000 H6C 2 0.455958 0.698396 0.025895 11.00000 -1.50000 AFIX 0 C7 1 0.263710 0.765101 0.034123 11.00000 0.05073 0.02357 = 0.02175 -0.00176 0.00866 0.00795 AFIX 137 H7A 2 0.210840 0.727745 0.009564 11.00000 -1.50000 H7B 2 0.264924 0.857557 0.020091 11.00000 -1.50000 H7C 2 0.272041 0.756530 0.091441 11.00000 -1.50000 AFIX 0 C5 1 0.315691 0.692788 -0.084492 11.00000 0.02253 0.02391 = 0.02743 0.00009 0.00875 0.00118 AFIX 137 H5A 2 0.355803 0.636442 -0.101731 11.00000 -1.50000 H5B 2 0.320786 0.781819 -0.103438 11.00000 -1.50000 H5C 2 0.260789 0.659917 -0.105928 11.00000 -1.50000 AFIX 0 SAME C8 C9' C10' C11' SADI C8 C9 C8 C10 C8 C11 SADI C9 C10 C10 C11 C11 C9 SIMU C8 > C11' 0.02 0.04 0.9 C8 1 0.387384 0.236767 0.126454 11.00000 0.02938 0.01617 = 0.02423 0.00101 0.00068 0.00240 PART 1 C9 1 0.327759 0.194312 0.176822 21.00000 0.04943 0.03339 = 0.03752 0.01532 0.01507 0.01047 AFIX 137 H9A 2 0.325005 0.261456 0.216354 21.00000 -1.50000 H9B 2 0.346206 0.111971 0.203240 21.00000 -1.50000 H9C 2 0.273695 0.182188 0.143288 21.00000 -1.50000 AFIX 0 C10 1 0.394094 0.136081 0.064222 21.00000 0.02773 0.01971 = 0.04068 -0.00725 0.00353 0.00046 AFIX 137 H10A 2 0.339748 0.116621 0.033149 21.00000 -1.50000 H10B 2 0.418494 0.056153 0.089710 21.00000 -1.50000 H10C 2 0.428381 0.170358 0.029564 21.00000 -1.50000 AFIX 0 C11 1 0.470977 0.261355 0.178214 21.00000 0.04268 0.01981 = 0.03506 -0.00105 -0.00617 0.00768 AFIX 137 H11A 2 0.508911 0.288399 0.145274 21.00000 -1.50000 H11B 2 0.490876 0.181118 0.206401 21.00000 -1.50000 H11C 2 0.466922 0.330365 0.216263 21.00000 -1.50000 AFIX 0 PART 2 C9' 1 0.323405 0.129900 0.125782 -21.00000 0.04918 0.02135 = 0.04257 0.00234 0.00564 -0.00371 AFIX 33 H9D 2 0.300823 0.103819 0.071357 -21.00000 -1.50000 H9E 2 0.279658 0.163286 0.149950 -21.00000 -1.50000 H9F 2 0.348831 0.054274 0.155608 -21.00000 -1.50000 AFIX 0 C10' 1 0.450013 0.189378 0.080473 -21.00000 0.03520 0.02556 = 0.03418 -0.00216 0.00564 0.00730 AFIX 33 H10D 2 0.475328 0.108869 0.104285 -21.00000 -1.50000 H10E 2 0.491913 0.256362 0.081841 -21.00000 -1.50000 H10F 2 0.423037 0.172456 0.025752 -21.00000 -1.50000 AFIX 0 C11' 1 0.427251 0.265705 0.211722 -21.00000 0.03884 0.01683 = 0.02813 0.00248 0.00105 -0.00019 AFIX 33 H11D 2 0.450153 0.185142 0.237577 -21.00000 -1.50000 H11E 2 0.386458 0.300706 0.239181 -21.00000 -1.50000 H11F 2 0.470798 0.329890 0.213280 -21.00000 -1.50000 AFIX 0 PART 0 C12 1 0.461325 0.525503 0.129966 11.00000 0.01866 0.01612 = 0.02562 -0.00419 -0.00119 0.00216 C13 1 0.527525 0.547143 0.332855 11.00000 0.02547 0.01272 = 0.02224 -0.00190 0.01188 -0.00026 C14 1 0.461636 0.480422 0.350396 11.00000 0.03396 0.02806 = 0.03659 -0.00588 0.01874 -0.00824 C15 1 0.466797 0.394069 0.412349 11.00000 0.08012 0.02261 = 0.05091 -0.00898 0.05217 -0.01961 C16 1 0.540284 0.373524 0.462180 11.00000 0.10152 0.01731 = 0.02712 0.00378 0.03433 0.00349 C17 1 0.605600 0.441848 0.450429 11.00000 0.06270 0.02242 = 0.01968 0.00084 0.01197 0.01766 C18 1 0.598952 0.526593 0.387833 11.00000 0.03183 0.01902 = 0.01912 0.00013 0.01109 0.00620 C19 1 0.595722 0.686919 0.224575 11.00000 0.01513 0.01636 = 0.01122 -0.00195 0.00021 -0.00280 C20 1 0.658064 0.598960 0.222700 11.00000 0.01840 0.01612 = 0.01389 -0.00137 0.00163 -0.00469 C21 1 0.727251 0.628221 0.195264 11.00000 0.01621 0.02238 = 0.01867 -0.00594 0.00405 0.00039 C22 1 0.735124 0.749436 0.163929 11.00000 0.02071 0.02859 = 0.01964 -0.00650 0.01026 -0.01214 C23 1 0.674104 0.838797 0.160681 11.00000 0.03004 0.01670 = 0.01776 0.00216 0.00511 -0.01086 C24 1 0.606858 0.806280 0.191165 11.00000 0.01864 0.01828 = 0.01683 -0.00244 0.00011 -0.00014 C25 1 0.471947 0.777294 0.291323 11.00000 0.01938 0.01857 = 0.01584 0.00206 0.00358 0.00240 C26 1 0.519107 0.860116 0.345187 11.00000 0.02313 0.01799 = 0.02069 0.00212 0.00708 0.00058 C27 1 0.489630 0.963021 0.381499 11.00000 0.04403 0.01779 = 0.02925 -0.00447 0.01745 -0.00513 C28 1 0.408028 0.986608 0.365837 11.00000 0.05446 0.02202 = 0.03656 0.00136 0.02661 0.01399 C29 1 0.357825 0.908781 0.313383 11.00000 0.02965 0.04512 = 0.02921 0.01167 0.01291 0.02185 C30 1 0.389636 0.806649 0.277599 11.00000 0.02054 0.03854 = 0.01611 0.00216 0.00010 0.00535 HKLF 4 ; _database_code_depnum_ccdc_archive 'CCDC 963627' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_eileen29 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H26 B Cl2 F15 N2 O2' _chemical_formula_weight 849.27 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.2938(8) _cell_length_b 10.6292(6) _cell_length_c 21.1241(8) _cell_angle_alpha 90.00 _cell_angle_beta 92.911(6) _cell_angle_gamma 90.00 _cell_volume 3429.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9833 _cell_measurement_theta_min 3.4823 _cell_measurement_theta_max 77.2358 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.645 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1712 _exptl_absorpt_coefficient_mu 2.791 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.58434 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'Nova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Xcalibur, Atlas, Nova' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3543 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 41645 _diffrn_reflns_av_R_equivalents 0.1329 _diffrn_reflns_av_sigmaI/netI 0.0650 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 4.19 _diffrn_reflns_theta_max 70.08 _reflns_number_total 6513 _reflns_number_gt 4937 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker XP' _computing_publication_material SHELXL-97 _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^)+(0.0572P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6513 _refine_ls_number_parameters 504 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0622 _refine_ls_R_factor_gt 0.0451 _refine_ls_wR_factor_ref 0.1199 _refine_ls_wR_factor_gt 0.1087 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _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 B B 0.28081(17) 0.7384(2) 0.39447(13) 0.0158(5) Uani 1 1 d . . . N1 N 0.28938(13) 0.59706(17) 0.18482(9) 0.0164(4) Uani 1 1 d . . . N2 N 0.14811(13) 0.62615(17) 0.19641(9) 0.0159(4) Uani 1 1 d . . . O1 O 0.26372(11) 0.68759(14) 0.32694(8) 0.0166(3) Uani 1 1 d . . . O2 O 0.24768(12) 0.85853(15) 0.26234(8) 0.0214(4) Uani 1 1 d . . . F1 F 0.42417(10) 0.89337(13) 0.46912(7) 0.0226(3) Uani 1 1 d . . . F2 F 0.58329(10) 0.81299(15) 0.50170(8) 0.0308(4) Uani 1 1 d . . . F3 F 0.63661(11) 0.57763(17) 0.46980(9) 0.0375(4) Uani 1 1 d . . . F4 F 0.52166(12) 0.42034(15) 0.40554(8) 0.0351(4) Uani 1 1 d . . . F5 F 0.35843(10) 0.49512(12) 0.37594(7) 0.0245(3) Uani 1 1 d . . . F6 F 0.12340(9) 0.87289(12) 0.44800(7) 0.0231(3) Uani 1 1 d . . . F7 F 0.10303(10) 1.11932(13) 0.45534(7) 0.0239(3) Uani 1 1 d . . . F8 F 0.22160(10) 1.27966(13) 0.40679(8) 0.0286(3) Uani 1 1 d . . . F9 F 0.36201(10) 1.18534(12) 0.34905(8) 0.0247(3) Uani 1 1 d . . . F10 F 0.38789(9) 0.93714(12) 0.34374(7) 0.0200(3) Uani 1 1 d . . . F11 F 0.28298(10) 0.77245(13) 0.52718(7) 0.0224(3) Uani 1 1 d . . . F12 F 0.20725(11) 0.63389(14) 0.61442(7) 0.0268(3) Uani 1 1 d . . . F13 F 0.09477(10) 0.44363(14) 0.57817(7) 0.0280(3) Uani 1 1 d . . . F14 F 0.06537(10) 0.39322(13) 0.45276(7) 0.0244(3) Uani 1 1 d . . . F15 F 0.14858(10) 0.51758(12) 0.36549(7) 0.0218(3) Uani 1 1 d . . . Cl1 Cl 0.20517(5) 0.22908(6) 0.73909(4) 0.03792(18) Uani 1 1 d . . . Cl2 Cl 0.34941(5) 0.37383(7) 0.68891(4) 0.03967(18) Uani 1 1 d . . . C1 C 0.22929(15) 0.6549(2) 0.21902(11) 0.0151(4) Uani 1 1 d . . . C2 C 0.24368(16) 0.5251(2) 0.13869(11) 0.0182(5) Uani 1 1 d . . . C3 C 0.15679(16) 0.5447(2) 0.14482(11) 0.0184(5) Uani 1 1 d . . . C4 C 0.38919(15) 0.6035(2) 0.19316(12) 0.0187(5) Uani 1 1 d . . . C5 C 0.41938(17) 0.7165(2) 0.23359(13) 0.0250(5) Uani 1 1 d . . . H5A H 0.3933 0.7936 0.2155 0.037 Uiso 1 1 calc R . . H5B H 0.4833 0.7228 0.2342 0.037 Uiso 1 1 calc R . . H5C H 0.4008 0.7054 0.2770 0.037 Uiso 1 1 calc R . . C6 C 0.42109(17) 0.4817(2) 0.22530(12) 0.0236(5) Uani 1 1 d . . . H6A H 0.3933 0.4721 0.2658 0.035 Uiso 1 1 calc R . . H6B H 0.4848 0.4850 0.2328 0.035 Uiso 1 1 calc R . . H6C H 0.4056 0.4100 0.1978 0.035 Uiso 1 1 calc R . . C7 C 0.42701(17) 0.6218(2) 0.12782(12) 0.0256(5) Uani 1 1 d . . . H7A H 0.4187 0.5446 0.1029 0.038 Uiso 1 1 calc R . . H7B H 0.4897 0.6407 0.1331 0.038 Uiso 1 1 calc R . . H7C H 0.3968 0.6916 0.1057 0.038 Uiso 1 1 calc R . . C8 C 0.28152(17) 0.4363(2) 0.09225(12) 0.0232(5) Uani 1 1 d . . . H8A H 0.2368 0.3752 0.0779 0.035 Uiso 1 1 calc R . . H8B H 0.3315 0.3919 0.1127 0.035 Uiso 1 1 calc R . . H8C H 0.3010 0.4838 0.0558 0.035 Uiso 1 1 calc R . . C9 C 0.08549(18) 0.4851(2) 0.10395(13) 0.0277(6) Uani 1 1 d . . . H9A H 0.1069 0.4683 0.0618 0.042 Uiso 1 1 calc R . . H9B H 0.0352 0.5421 0.1000 0.042 Uiso 1 1 calc R . . H9C H 0.0677 0.4059 0.1232 0.042 Uiso 1 1 calc R . . C10 C 0.06005(15) 0.6737(2) 0.21773(12) 0.0180(5) Uani 1 1 d . . . C11 C 0.06733(16) 0.7461(2) 0.28025(12) 0.0227(5) Uani 1 1 d . . . H11A H 0.0975 0.6941 0.3128 0.034 Uiso 1 1 calc R . . H11B H 0.0086 0.7670 0.2935 0.034 Uiso 1 1 calc R . . H11C H 0.1006 0.8238 0.2745 0.034 Uiso 1 1 calc R . . C12 C 0.02116(16) 0.7612(2) 0.16606(12) 0.0230(5) Uani 1 1 d . . . H12A H 0.0579 0.8363 0.1634 0.035 Uiso 1 1 calc R . . H12B H -0.0381 0.7860 0.1765 0.035 Uiso 1 1 calc R . . H12C H 0.0188 0.7172 0.1252 0.035 Uiso 1 1 calc R . . C13 C 0.00219(17) 0.5590(2) 0.22877(14) 0.0273(6) Uani 1 1 d . . . H13A H -0.0109 0.5160 0.1884 0.041 Uiso 1 1 calc R . . H13B H -0.0526 0.5865 0.2466 0.041 Uiso 1 1 calc R . . H13C H 0.0330 0.5013 0.2584 0.041 Uiso 1 1 calc R . . C14 C 0.24918(15) 0.7468(2) 0.27348(11) 0.0168(5) Uani 1 1 d . . . C15 C 0.38309(16) 0.7018(2) 0.41600(11) 0.0181(5) Uani 1 1 d . . . C16 C 0.44411(16) 0.7755(2) 0.44998(12) 0.0197(5) Uani 1 1 d . . . C17 C 0.52827(17) 0.7361(2) 0.46817(12) 0.0236(5) Uani 1 1 d . . . C18 C 0.55541(17) 0.6168(3) 0.45277(13) 0.0262(6) Uani 1 1 d . . . C19 C 0.49716(18) 0.5386(2) 0.42019(12) 0.0251(5) Uani 1 1 d . . . C20 C 0.41335(17) 0.5806(2) 0.40372(12) 0.0205(5) Uani 1 1 d . . . C21 C 0.25974(15) 0.8899(2) 0.39772(11) 0.0159(4) Uani 1 1 d . . . C22 C 0.18715(16) 0.9445(2) 0.42390(11) 0.0179(5) Uani 1 1 d . . . C23 C 0.17354(16) 1.0733(2) 0.42738(11) 0.0182(5) Uani 1 1 d . . . C24 C 0.23291(16) 1.1550(2) 0.40287(12) 0.0189(5) Uani 1 1 d . . . C25 C 0.30460(16) 1.1066(2) 0.37431(12) 0.0194(5) Uani 1 1 d . . . C26 C 0.31646(15) 0.9780(2) 0.37234(11) 0.0177(5) Uani 1 1 d . . . C27 C 0.22112(15) 0.6539(2) 0.44142(11) 0.0162(4) Uani 1 1 d . . . C28 C 0.23098(16) 0.6764(2) 0.50633(12) 0.0176(5) Uani 1 1 d . . . C29 C 0.19152(16) 0.6079(2) 0.55237(11) 0.0192(5) Uani 1 1 d . . . C30 C 0.13538(16) 0.5117(2) 0.53437(12) 0.0205(5) Uani 1 1 d . . . C31 C 0.12144(15) 0.4859(2) 0.47078(12) 0.0182(5) Uani 1 1 d . . . C32 C 0.16477(16) 0.5539(2) 0.42614(11) 0.0172(5) Uani 1 1 d . . . C33 C 0.2376(2) 0.3710(3) 0.70433(19) 0.0415(8) Uani 1 1 d . . . H33A H 0.2027 0.3838 0.6641 0.050 Uiso 1 1 calc R . . H33B H 0.2248 0.4416 0.7330 0.050 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 B 0.0166(12) 0.0107(11) 0.0203(13) -0.0030(9) 0.0023(10) 0.0006(9) N1 0.0150(10) 0.0133(9) 0.0212(10) 0.0014(7) 0.0026(8) 0.0016(7) N2 0.0162(10) 0.0127(9) 0.0191(10) -0.0007(7) 0.0026(8) 0.0005(7) O1 0.0195(8) 0.0123(7) 0.0180(8) 0.0003(6) 0.0012(7) 0.0002(6) O2 0.0286(9) 0.0117(8) 0.0237(8) 0.0008(6) 0.0005(7) 0.0006(6) F1 0.0236(7) 0.0166(7) 0.0275(7) -0.0028(5) -0.0003(6) -0.0014(5) F2 0.0211(8) 0.0382(9) 0.0325(8) 0.0059(6) -0.0034(7) -0.0076(6) F3 0.0213(8) 0.0500(10) 0.0414(10) 0.0144(8) 0.0044(7) 0.0142(7) F4 0.0416(10) 0.0257(8) 0.0390(9) 0.0049(7) 0.0099(8) 0.0202(7) F5 0.0326(8) 0.0135(7) 0.0276(7) -0.0011(5) 0.0027(6) 0.0026(6) F6 0.0172(7) 0.0152(7) 0.0376(8) 0.0035(6) 0.0084(6) 0.0002(5) F7 0.0226(7) 0.0178(7) 0.0320(8) 0.0005(5) 0.0078(6) 0.0072(5) F8 0.0293(8) 0.0105(7) 0.0467(9) 0.0002(6) 0.0081(7) 0.0039(5) F9 0.0195(7) 0.0150(7) 0.0403(9) 0.0039(6) 0.0061(6) -0.0023(5) F10 0.0170(7) 0.0163(6) 0.0274(7) -0.0002(5) 0.0078(6) 0.0011(5) F11 0.0253(8) 0.0205(7) 0.0215(7) -0.0052(5) 0.0015(6) -0.0071(6) F12 0.0324(8) 0.0297(8) 0.0187(7) -0.0021(6) 0.0045(6) -0.0035(6) F13 0.0304(8) 0.0248(7) 0.0296(8) 0.0060(6) 0.0100(7) -0.0053(6) F14 0.0234(8) 0.0153(7) 0.0343(8) -0.0003(5) 0.0017(6) -0.0067(5) F15 0.0292(8) 0.0156(7) 0.0204(7) -0.0021(5) -0.0016(6) -0.0036(5) Cl1 0.0276(3) 0.0292(3) 0.0578(5) -0.0101(3) 0.0101(3) -0.0032(3) Cl2 0.0365(4) 0.0368(4) 0.0469(4) 0.0046(3) 0.0147(3) -0.0008(3) C1 0.0146(11) 0.0122(10) 0.0188(11) 0.0005(8) 0.0029(9) 0.0001(8) C2 0.0230(12) 0.0125(10) 0.0192(11) -0.0001(8) 0.0022(10) 0.0007(8) C3 0.0201(12) 0.0143(10) 0.0208(11) -0.0018(9) 0.0020(9) -0.0004(8) C4 0.0122(11) 0.0220(12) 0.0221(12) 0.0009(9) 0.0022(9) 0.0009(8) C5 0.0164(12) 0.0261(13) 0.0324(14) -0.0043(10) 0.0009(10) -0.0028(9) C6 0.0222(13) 0.0253(13) 0.0235(12) 0.0039(9) 0.0035(10) 0.0065(10) C7 0.0176(12) 0.0347(14) 0.0252(13) 0.0066(10) 0.0060(10) -0.0002(10) C8 0.0241(13) 0.0228(12) 0.0229(12) -0.0064(9) 0.0030(10) 0.0047(9) C9 0.0257(14) 0.0251(13) 0.0321(14) -0.0088(10) -0.0005(11) -0.0009(10) C10 0.0113(11) 0.0155(11) 0.0274(12) 0.0012(9) 0.0031(9) 0.0010(8) C11 0.0203(12) 0.0217(12) 0.0265(13) -0.0002(9) 0.0051(10) 0.0077(9) C12 0.0179(12) 0.0217(12) 0.0293(13) 0.0016(10) -0.0004(10) 0.0034(9) C13 0.0219(13) 0.0168(12) 0.0438(16) 0.0013(10) 0.0089(12) -0.0027(9) C14 0.0130(11) 0.0149(11) 0.0226(12) -0.0015(9) 0.0019(9) 0.0003(8) C15 0.0194(12) 0.0176(11) 0.0175(11) 0.0000(8) 0.0037(9) 0.0013(9) C16 0.0192(12) 0.0180(11) 0.0222(12) 0.0033(9) 0.0049(10) 0.0017(9) C17 0.0195(12) 0.0303(13) 0.0210(12) 0.0068(10) 0.0011(10) -0.0034(10) C18 0.0161(12) 0.0348(14) 0.0280(13) 0.0104(10) 0.0046(10) 0.0087(10) C19 0.0292(14) 0.0214(12) 0.0257(12) 0.0061(10) 0.0101(11) 0.0120(10) C20 0.0241(13) 0.0173(11) 0.0205(11) 0.0012(9) 0.0044(10) 0.0028(9) C21 0.0152(11) 0.0134(11) 0.0192(11) -0.0011(8) 0.0012(9) -0.0006(8) C22 0.0158(11) 0.0174(11) 0.0206(11) 0.0000(9) 0.0032(9) -0.0028(8) C23 0.0135(11) 0.0190(11) 0.0224(11) -0.0017(9) 0.0034(9) 0.0037(8) C24 0.0198(12) 0.0083(10) 0.0283(12) -0.0004(9) -0.0020(10) 0.0024(8) C25 0.0162(11) 0.0138(11) 0.0280(13) 0.0031(9) -0.0005(10) -0.0039(8) C26 0.0149(11) 0.0157(11) 0.0225(12) -0.0023(9) 0.0024(9) 0.0016(8) C27 0.0164(11) 0.0113(10) 0.0209(11) -0.0009(8) 0.0002(9) 0.0017(8) C28 0.0163(11) 0.0123(10) 0.0242(12) -0.0011(8) 0.0018(9) -0.0005(8) C29 0.0185(12) 0.0205(11) 0.0187(11) -0.0016(9) 0.0017(9) 0.0017(9) C30 0.0189(12) 0.0168(11) 0.0266(13) 0.0058(9) 0.0095(10) 0.0019(9) C31 0.0153(11) 0.0117(10) 0.0277(12) -0.0017(9) 0.0018(9) -0.0014(8) C32 0.0187(11) 0.0137(10) 0.0191(11) -0.0012(8) 0.0004(9) 0.0026(8) C33 0.0296(16) 0.0216(14) 0.072(2) 0.0018(14) -0.0053(15) 0.0032(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 B O1 1.535(3) . ? B C21 1.645(3) . ? B C27 1.648(3) . ? B C15 1.653(3) . ? N1 C1 1.346(3) . ? N1 C2 1.398(3) . ? N1 C4 1.529(3) . ? N2 C1 1.343(3) . ? N2 C3 1.403(3) . ? N2 C10 1.528(3) . ? O1 C14 1.302(3) . ? O2 C14 1.211(3) . ? F1 C16 1.356(3) . ? F2 C17 1.348(3) . ? F3 C18 1.342(3) . ? F4 C19 1.352(3) . ? F5 C20 1.351(3) . ? F6 C22 1.356(3) . ? F7 C23 1.348(3) . ? F8 C24 1.340(3) . ? F9 C25 1.343(3) . ? F10 C26 1.347(3) . ? F11 C28 1.354(3) . ? F12 C29 1.349(3) . ? F13 C30 1.350(3) . ? F14 C31 1.348(3) . ? F15 C32 1.349(3) . ? Cl1 C33 1.760(3) . ? Cl2 C33 1.757(3) . ? C1 C14 1.528(3) . ? C2 C3 1.358(4) . ? C2 C8 1.498(3) . ? C3 C9 1.497(3) . ? C4 C6 1.531(3) . ? C4 C5 1.531(3) . ? C4 C7 1.536(3) . ? C10 C11 1.528(3) . ? C10 C12 1.531(3) . ? C10 C13 1.531(3) . ? C15 C16 1.390(3) . ? C15 C20 1.397(3) . ? C16 C17 1.389(4) . ? C17 C18 1.378(4) . ? C18 C19 1.378(4) . ? C19 C20 1.385(4) . ? C21 C22 1.392(3) . ? C21 C26 1.402(3) . ? C22 C23 1.387(3) . ? C23 C24 1.376(3) . ? C24 C25 1.377(4) . ? C25 C26 1.380(3) . ? C27 C28 1.392(3) . ? C27 C32 1.396(3) . ? C28 C29 1.378(3) . ? C29 C30 1.376(3) . ? C30 C31 1.377(4) . ? C31 C32 1.383(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 O1 B C21 111.01(19) . . ? O1 B C27 107.12(18) . . ? C21 B C27 113.13(19) . . ? O1 B C15 106.68(18) . . ? C21 B C15 113.80(19) . . ? C27 B C15 104.57(18) . . ? C1 N1 C2 107.0(2) . . ? C1 N1 C4 128.5(2) . . ? C2 N1 C4 124.45(19) . . ? C1 N2 C3 107.12(19) . . ? C1 N2 C10 129.27(19) . . ? C3 N2 C10 123.5(2) . . ? C14 O1 B 130.51(17) . . ? N2 C1 N1 110.5(2) . . ? N2 C1 C14 123.9(2) . . ? N1 C1 C14 125.5(2) . . ? C3 C2 N1 107.8(2) . . ? C3 C2 C8 124.9(2) . . ? N1 C2 C8 127.2(2) . . ? C2 C3 N2 107.5(2) . . ? C2 C3 C9 124.6(2) . . ? N2 C3 C9 127.9(2) . . ? N1 C4 C6 107.86(19) . . ? N1 C4 C5 111.75(19) . . ? C6 C4 C5 109.6(2) . . ? N1 C4 C7 108.8(2) . . ? C6 C4 C7 112.3(2) . . ? C5 C4 C7 106.6(2) . . ? N2 C10 C11 113.27(19) . . ? N2 C10 C12 107.89(19) . . ? C11 C10 C12 108.58(19) . . ? N2 C10 C13 107.85(18) . . ? C11 C10 C13 106.7(2) . . ? C12 C10 C13 112.7(2) . . ? O2 C14 O1 130.0(2) . . ? O2 C14 C1 118.7(2) . . ? O1 C14 C1 111.27(18) . . ? C16 C15 C20 113.3(2) . . ? C16 C15 B 127.6(2) . . ? C20 C15 B 118.9(2) . . ? F1 C16 C17 114.5(2) . . ? F1 C16 C15 121.3(2) . . ? C17 C16 C15 124.2(2) . . ? F2 C17 C18 119.6(2) . . ? F2 C17 C16 120.5(2) . . ? C18 C17 C16 119.8(2) . . ? F3 C18 C19 120.8(2) . . ? F3 C18 C17 120.6(3) . . ? C19 C18 C17 118.6(2) . . ? F4 C19 C18 119.7(2) . . ? F4 C19 C20 120.4(3) . . ? C18 C19 C20 119.8(2) . . ? F5 C20 C19 116.0(2) . . ? F5 C20 C15 119.7(2) . . ? C19 C20 C15 124.2(2) . . ? C22 C21 C26 113.3(2) . . ? C22 C21 B 125.9(2) . . ? C26 C21 B 120.8(2) . . ? F6 C22 C23 114.9(2) . . ? F6 C22 C21 121.2(2) . . ? C23 C22 C21 123.8(2) . . ? F7 C23 C24 119.6(2) . . ? F7 C23 C22 120.5(2) . . ? C24 C23 C22 119.9(2) . . ? F8 C24 C23 120.7(2) . . ? F8 C24 C25 120.3(2) . . ? C23 C24 C25 119.0(2) . . ? F9 C25 C24 119.5(2) . . ? F9 C25 C26 121.0(2) . . ? C24 C25 C26 119.4(2) . . ? F10 C26 C25 116.4(2) . . ? F10 C26 C21 119.2(2) . . ? C25 C26 C21 124.4(2) . . ? C28 C27 C32 113.1(2) . . ? C28 C27 B 117.6(2) . . ? C32 C27 B 129.1(2) . . ? F11 C28 C29 116.1(2) . . ? F11 C28 C27 118.8(2) . . ? C29 C28 C27 125.1(2) . . ? F12 C29 C30 119.9(2) . . ? F12 C29 C28 121.0(2) . . ? C30 C29 C28 119.1(2) . . ? F13 C30 C29 120.7(2) . . ? F13 C30 C31 120.5(2) . . ? C29 C30 C31 118.7(2) . . ? F14 C31 C30 119.1(2) . . ? F14 C31 C32 120.6(2) . . ? C30 C31 C32 120.4(2) . . ? F15 C32 C31 115.3(2) . . ? F15 C32 C27 121.3(2) . . ? C31 C32 C27 123.5(2) . . ? Cl2 C33 Cl1 112.94(16) . . ? 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 C21 B O1 C14 11.6(3) . . . . ? C27 B O1 C14 135.6(2) . . . . ? C15 B O1 C14 -112.9(2) . . . . ? C3 N2 C1 N1 0.2(2) . . . . ? C10 N2 C1 N1 -176.9(2) . . . . ? C3 N2 C1 C14 176.9(2) . . . . ? C10 N2 C1 C14 -0.3(4) . . . . ? C2 N1 C1 N2 -1.4(2) . . . . ? C4 N1 C1 N2 179.4(2) . . . . ? C2 N1 C1 C14 -178.0(2) . . . . ? C4 N1 C1 C14 2.9(4) . . . . ? C1 N1 C2 C3 2.1(3) . . . . ? C4 N1 C2 C3 -178.7(2) . . . . ? C1 N1 C2 C8 -175.1(2) . . . . ? C4 N1 C2 C8 4.1(4) . . . . ? N1 C2 C3 N2 -1.9(3) . . . . ? C8 C2 C3 N2 175.3(2) . . . . ? N1 C2 C3 C9 179.7(2) . . . . ? C8 C2 C3 C9 -3.0(4) . . . . ? C1 N2 C3 C2 1.1(3) . . . . ? C10 N2 C3 C2 178.5(2) . . . . ? C1 N2 C3 C9 179.4(2) . . . . ? C10 N2 C3 C9 -3.2(4) . . . . ? C1 N1 C4 C6 103.1(3) . . . . ? C2 N1 C4 C6 -75.9(3) . . . . ? C1 N1 C4 C5 -17.5(3) . . . . ? C2 N1 C4 C5 163.5(2) . . . . ? C1 N1 C4 C7 -134.9(2) . . . . ? C2 N1 C4 C7 46.1(3) . . . . ? C1 N2 C10 C11 -11.2(3) . . . . ? C3 N2 C10 C11 172.0(2) . . . . ? C1 N2 C10 C12 109.0(3) . . . . ? C3 N2 C10 C12 -67.8(3) . . . . ? C1 N2 C10 C13 -129.0(2) . . . . ? C3 N2 C10 C13 54.2(3) . . . . ? B O1 C14 O2 2.4(4) . . . . ? B O1 C14 C1 -176.0(2) . . . . ? N2 C1 C14 O2 -80.4(3) . . . . ? N1 C1 C14 O2 95.8(3) . . . . ? N2 C1 C14 O1 98.2(3) . . . . ? N1 C1 C14 O1 -85.7(3) . . . . ? O1 B C15 C16 140.0(2) . . . . ? C21 B C15 C16 17.2(3) . . . . ? C27 B C15 C16 -106.7(3) . . . . ? O1 B C15 C20 -45.0(3) . . . . ? C21 B C15 C20 -167.8(2) . . . . ? C27 B C15 C20 68.3(3) . . . . ? C20 C15 C16 F1 -176.3(2) . . . . ? B C15 C16 F1 -1.1(4) . . . . ? C20 C15 C16 C17 2.4(4) . . . . ? B C15 C16 C17 177.7(2) . . . . ? F1 C16 C17 F2 -0.5(3) . . . . ? C15 C16 C17 F2 -179.3(2) . . . . ? F1 C16 C17 C18 178.5(2) . . . . ? C15 C16 C17 C18 -0.4(4) . . . . ? F2 C17 C18 F3 -1.3(4) . . . . ? C16 C17 C18 F3 179.8(2) . . . . ? F2 C17 C18 C19 178.0(2) . . . . ? C16 C17 C18 C19 -0.9(4) . . . . ? F3 C18 C19 F4 0.5(4) . . . . ? C17 C18 C19 F4 -178.8(2) . . . . ? F3 C18 C19 C20 179.3(2) . . . . ? C17 C18 C19 C20 0.0(4) . . . . ? F4 C19 C20 F5 3.4(3) . . . . ? C18 C19 C20 F5 -175.4(2) . . . . ? F4 C19 C20 C15 -178.8(2) . . . . ? C18 C19 C20 C15 2.4(4) . . . . ? C16 C15 C20 F5 174.3(2) . . . . ? B C15 C20 F5 -1.4(3) . . . . ? C16 C15 C20 C19 -3.5(4) . . . . ? B C15 C20 C19 -179.2(2) . . . . ? O1 B C21 C22 105.6(3) . . . . ? C27 B C21 C22 -14.8(3) . . . . ? C15 B C21 C22 -134.0(2) . . . . ? O1 B C21 C26 -73.7(3) . . . . ? C27 B C21 C26 165.8(2) . . . . ? C15 B C21 C26 46.6(3) . . . . ? C26 C21 C22 F6 177.0(2) . . . . ? B C21 C22 F6 -2.5(4) . . . . ? C26 C21 C22 C23 -2.7(4) . . . . ? B C21 C22 C23 177.9(2) . . . . ? F6 C22 C23 F7 2.5(3) . . . . ? C21 C22 C23 F7 -177.8(2) . . . . ? F6 C22 C23 C24 -178.3(2) . . . . ? C21 C22 C23 C24 1.4(4) . . . . ? F7 C23 C24 F8 0.3(4) . . . . ? C22 C23 C24 F8 -178.8(2) . . . . ? F7 C23 C24 C25 -179.9(2) . . . . ? C22 C23 C24 C25 0.9(4) . . . . ? F8 C24 C25 F9 -1.6(4) . . . . ? C23 C24 C25 F9 178.6(2) . . . . ? F8 C24 C25 C26 178.2(2) . . . . ? C23 C24 C25 C26 -1.6(4) . . . . ? F9 C25 C26 F10 -0.2(3) . . . . ? C24 C25 C26 F10 -180.0(2) . . . . ? F9 C25 C26 C21 179.8(2) . . . . ? C24 C25 C26 C21 0.1(4) . . . . ? C22 C21 C26 F10 -177.9(2) . . . . ? B C21 C26 F10 1.5(3) . . . . ? C22 C21 C26 C25 2.0(4) . . . . ? B C21 C26 C25 -178.5(2) . . . . ? O1 B C27 C28 175.10(19) . . . . ? C21 B C27 C28 -62.2(3) . . . . ? C15 B C27 C28 62.1(2) . . . . ? O1 B C27 C32 0.2(3) . . . . ? C21 B C27 C32 122.9(3) . . . . ? C15 B C27 C32 -112.7(3) . . . . ? C32 C27 C28 F11 -178.9(2) . . . . ? B C27 C28 F11 5.4(3) . . . . ? C32 C27 C28 C29 1.0(3) . . . . ? B C27 C28 C29 -174.6(2) . . . . ? F11 C28 C29 F12 -2.3(3) . . . . ? C27 C28 C29 F12 177.7(2) . . . . ? F11 C28 C29 C30 177.7(2) . . . . ? C27 C28 C29 C30 -2.2(4) . . . . ? F12 C29 C30 F13 0.8(4) . . . . ? C28 C29 C30 F13 -179.2(2) . . . . ? F12 C29 C30 C31 -179.1(2) . . . . ? C28 C29 C30 C31 0.9(4) . . . . ? F13 C30 C31 F14 1.2(3) . . . . ? C29 C30 C31 F14 -178.9(2) . . . . ? F13 C30 C31 C32 -178.5(2) . . . . ? C29 C30 C31 C32 1.4(4) . . . . ? F14 C31 C32 F15 -2.0(3) . . . . ? C30 C31 C32 F15 177.7(2) . . . . ? F14 C31 C32 C27 177.6(2) . . . . ? C30 C31 C32 C27 -2.7(4) . . . . ? C28 C27 C32 F15 -179.0(2) . . . . ? B C27 C32 F15 -3.9(4) . . . . ? C28 C27 C32 C31 1.5(3) . . . . ? B C27 C32 C31 176.5(2) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 70.08 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.303 _refine_diff_density_min -0.448 _refine_diff_density_rms 0.069 _iucr_refine_instructions_details ; TITL eileen29 in P2(1)/c CELL 1.54184 15.2938 10.6292 21.1241 90.000 92.911 90.000 ZERR 4.00 0.0008 0.0006 0.0008 0.000 0.006 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H B N O F CL UNIT 132 104 4 8 8 60 8 SIZE 0.08 0.07 0.03 TEMP -173 SHEL 999 0.82 ACTA CONF FMAP 2 PLAN 10 L.S. 8 WGHT 0.057200 FVAR 1.21728 B 3 0.280809 0.738356 0.394470 11.00000 0.01661 0.01069 = 0.02025 -0.00302 0.00231 0.00064 N1 4 0.289382 0.597060 0.184822 11.00000 0.01503 0.01325 = 0.02119 0.00136 0.00265 0.00156 N2 4 0.148110 0.626145 0.196410 11.00000 0.01618 0.01269 = 0.01907 -0.00072 0.00260 0.00046 O1 5 0.263723 0.687593 0.326944 11.00000 0.01946 0.01231 = 0.01797 0.00025 0.00118 0.00019 O2 5 0.247677 0.858529 0.262338 11.00000 0.02860 0.01169 = 0.02370 0.00082 0.00046 0.00057 F1 6 0.424172 0.893373 0.469122 11.00000 0.02357 0.01658 = 0.02755 -0.00276 -0.00027 -0.00139 F2 6 0.583287 0.812985 0.501705 11.00000 0.02108 0.03820 = 0.03249 0.00586 -0.00341 -0.00758 F3 6 0.636613 0.577627 0.469801 11.00000 0.02131 0.04999 = 0.04143 0.01440 0.00440 0.01423 F4 6 0.521663 0.420335 0.405541 11.00000 0.04162 0.02567 = 0.03896 0.00489 0.00990 0.02023 F5 6 0.358432 0.495122 0.375935 11.00000 0.03260 0.01349 = 0.02764 -0.00114 0.00272 0.00263 F6 6 0.123396 0.872887 0.448005 11.00000 0.01720 0.01517 = 0.03761 0.00349 0.00842 0.00017 F7 6 0.103031 1.119322 0.455337 11.00000 0.02262 0.01775 = 0.03202 0.00051 0.00784 0.00716 F8 6 0.221605 1.279656 0.406790 11.00000 0.02929 0.01045 = 0.04668 0.00023 0.00808 0.00387 F9 6 0.362013 1.185341 0.349049 11.00000 0.01947 0.01496 = 0.04026 0.00391 0.00613 -0.00232 F10 6 0.387885 0.937143 0.343739 11.00000 0.01700 0.01632 = 0.02743 -0.00023 0.00783 0.00107 F11 6 0.282979 0.772452 0.527180 11.00000 0.02530 0.02047 = 0.02151 -0.00522 0.00148 -0.00714 F12 6 0.207246 0.633885 0.614417 11.00000 0.03242 0.02973 = 0.01868 -0.00213 0.00448 -0.00354 F13 6 0.094771 0.443626 0.578174 11.00000 0.03044 0.02479 = 0.02957 0.00601 0.01003 -0.00528 F14 6 0.065368 0.393223 0.452759 11.00000 0.02344 0.01534 = 0.03434 -0.00034 0.00170 -0.00672 F15 6 0.148575 0.517578 0.365494 11.00000 0.02924 0.01564 = 0.02037 -0.00211 -0.00160 -0.00355 CL1 7 0.205168 0.229080 0.739094 11.00000 0.02762 0.02917 = 0.05778 -0.01014 0.01011 -0.00323 CL2 7 0.349407 0.373831 0.688906 11.00000 0.03650 0.03685 = 0.04695 0.00461 0.01473 -0.00083 C1 1 0.229294 0.654885 0.219017 11.00000 0.01465 0.01219 = 0.01878 0.00048 0.00293 0.00013 C2 1 0.243675 0.525063 0.138691 11.00000 0.02305 0.01248 = 0.01919 -0.00014 0.00220 0.00073 C3 1 0.156790 0.544724 0.144822 11.00000 0.02013 0.01426 = 0.02082 -0.00182 0.00201 -0.00043 C4 1 0.389194 0.603548 0.193156 11.00000 0.01223 0.02200 = 0.02210 0.00092 0.00224 0.00088 C5 1 0.419385 0.716498 0.233587 11.00000 0.01642 0.02607 = 0.03242 -0.00431 0.00093 -0.00282 AFIX 137 H5A 2 0.393321 0.793587 0.215528 11.00000 -1.50000 H5B 2 0.483347 0.722835 0.234157 11.00000 -1.50000 H5C 2 0.400812 0.705370 0.276956 11.00000 -1.50000 AFIX 0 C6 1 0.421093 0.481682 0.225304 11.00000 0.02223 0.02528 = 0.02346 0.00390 0.00351 0.00654 AFIX 137 H6A 2 0.393332 0.472062 0.265827 11.00000 -1.50000 H6B 2 0.484810 0.485008 0.232834 11.00000 -1.50000 H6C 2 0.405559 0.409959 0.197832 11.00000 -1.50000 AFIX 0 C7 1 0.427006 0.621774 0.127815 11.00000 0.01756 0.03471 = 0.02517 0.00664 0.00598 -0.00018 AFIX 137 H7A 2 0.418684 0.544586 0.102860 11.00000 -1.50000 H7B 2 0.489658 0.640721 0.133143 11.00000 -1.50000 H7C 2 0.396806 0.691644 0.105744 11.00000 -1.50000 AFIX 0 C8 1 0.281522 0.436342 0.092251 11.00000 0.02408 0.02282 = 0.02292 -0.00643 0.00296 0.00471 AFIX 137 H8A 2 0.236824 0.375210 0.077898 11.00000 -1.50000 H8B 2 0.331515 0.391933 0.112697 11.00000 -1.50000 H8C 2 0.300984 0.483845 0.055779 11.00000 -1.50000 AFIX 0 C9 1 0.085490 0.485109 0.103950 11.00000 0.02568 0.02509 = 0.03212 -0.00884 -0.00051 -0.00090 AFIX 137 H9A 2 0.106927 0.468284 0.061839 11.00000 -1.50000 H9B 2 0.035152 0.542128 0.100010 11.00000 -1.50000 H9C 2 0.067708 0.405885 0.123242 11.00000 -1.50000 AFIX 0 C10 1 0.060053 0.673695 0.217733 11.00000 0.01132 0.01546 = 0.02737 0.00116 0.00307 0.00101 C11 1 0.067330 0.746134 0.280248 11.00000 0.02030 0.02173 = 0.02652 -0.00024 0.00512 0.00766 AFIX 137 H11A 2 0.097496 0.694066 0.312823 11.00000 -1.50000 H11B 2 0.008581 0.767032 0.293490 11.00000 -1.50000 H11C 2 0.100581 0.823770 0.274532 11.00000 -1.50000 AFIX 0 C12 1 0.021156 0.761198 0.166065 11.00000 0.01790 0.02166 = 0.02929 0.00164 -0.00038 0.00343 AFIX 137 H12A 2 0.057911 0.836338 0.163363 11.00000 -1.50000 H12B 2 -0.038109 0.786042 0.176522 11.00000 -1.50000 H12C 2 0.018768 0.717220 0.125239 11.00000 -1.50000 AFIX 0 C13 1 0.002194 0.559034 0.228770 11.00000 0.02186 0.01683 = 0.04383 0.00126 0.00894 -0.00270 AFIX 137 H13A 2 -0.010894 0.515967 0.188375 11.00000 -1.50000 H13B 2 -0.052553 0.586482 0.246619 11.00000 -1.50000 H13C 2 0.032992 0.501253 0.258382 11.00000 -1.50000 AFIX 0 C14 1 0.249181 0.746797 0.273481 11.00000 0.01303 0.01490 = 0.02259 -0.00151 0.00192 0.00030 C15 1 0.383091 0.701765 0.416002 11.00000 0.01939 0.01762 = 0.01753 0.00004 0.00373 0.00128 C16 1 0.444112 0.775478 0.449981 11.00000 0.01919 0.01799 = 0.02217 0.00330 0.00493 0.00171 C17 1 0.528267 0.736138 0.468172 11.00000 0.01946 0.03028 = 0.02103 0.00677 0.00107 -0.00336 C18 1 0.555413 0.616844 0.452770 11.00000 0.01614 0.03481 = 0.02799 0.01041 0.00457 0.00871 C19 1 0.497158 0.538559 0.420187 11.00000 0.02920 0.02141 = 0.02572 0.00611 0.01010 0.01199 C20 1 0.413353 0.580596 0.403720 11.00000 0.02414 0.01726 = 0.02045 0.00124 0.00438 0.00280 C21 1 0.259743 0.889916 0.397716 11.00000 0.01522 0.01341 = 0.01925 -0.00110 0.00116 -0.00062 C22 1 0.187149 0.944467 0.423904 11.00000 0.01582 0.01741 = 0.02060 -0.00004 0.00316 -0.00278 C23 1 0.173545 1.073278 0.427375 11.00000 0.01354 0.01899 = 0.02243 -0.00174 0.00337 0.00368 C24 1 0.232912 1.154978 0.402866 11.00000 0.01982 0.00826 = 0.02832 -0.00041 -0.00199 0.00241 C25 1 0.304600 1.106648 0.374313 11.00000 0.01621 0.01380 = 0.02798 0.00310 -0.00048 -0.00393 C26 1 0.316456 0.978034 0.372336 11.00000 0.01488 0.01573 = 0.02252 -0.00228 0.00242 0.00164 C27 1 0.221116 0.653889 0.441424 11.00000 0.01643 0.01125 = 0.02092 -0.00091 0.00023 0.00167 C28 1 0.230982 0.676353 0.506334 11.00000 0.01626 0.01232 = 0.02421 -0.00108 0.00175 -0.00054 C29 1 0.191520 0.607880 0.552366 11.00000 0.01850 0.02050 = 0.01871 -0.00157 0.00172 0.00174 C30 1 0.135379 0.511696 0.534368 11.00000 0.01887 0.01681 = 0.02665 0.00584 0.00953 0.00190 C31 1 0.121439 0.485925 0.470784 11.00000 0.01532 0.01175 = 0.02775 -0.00170 0.00176 -0.00145 C32 1 0.164766 0.553899 0.426140 11.00000 0.01870 0.01373 = 0.01909 -0.00121 0.00042 0.00260 C33 1 0.237607 0.370967 0.704327 11.00000 0.02964 0.02162 = 0.07235 0.00183 -0.00532 0.00323 AFIX 23 H33A 2 0.202718 0.383810 0.664079 11.00000 -1.20000 H33B 2 0.224755 0.441564 0.732979 11.00000 -1.20000 HKLF 4 ; #============================================================================= # end of cif data for "eileen29" (compound 9b) #============================================================================= #============================================================================= # end of combined cif data #============================================================================= _database_code_depnum_ccdc_archive 'CCDC 963628' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_temp_eileen35 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H20 N4 O' _chemical_formula_weight 224.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/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 9.2956(2) _cell_length_b 11.7049(2) _cell_length_c 11.2144(2) _cell_angle_alpha 90.00 _cell_angle_beta 99.208(2) _cell_angle_gamma 90.00 _cell_volume 1204.45(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 14116 _cell_measurement_theta_min 3.7733 _cell_measurement_theta_max 75.7649 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.237 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.664 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.53914 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'Nova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur, Atlas, Nova' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3543 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19755 _diffrn_reflns_av_R_equivalents 0.0229 _diffrn_reflns_av_sigmaI/netI 0.0098 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 5.50 _diffrn_reflns_theta_max 75.95 _reflns_number_total 2504 _reflns_number_gt 2365 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'BRUKER XP' _computing_publication_material SHELXL-97 _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 atoms N4 and O are disordered over two positions with relative occupation 9:1. The dimensions of the minor component are unatisfactory despite the use of simmilarity restraints. ; _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^)+(0.0491P)^2^+0.3782P] 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 2504 _refine_ls_number_parameters 160 _refine_ls_number_restraints 15 _refine_ls_R_factor_all 0.0372 _refine_ls_R_factor_gt 0.0356 _refine_ls_wR_factor_ref 0.0934 _refine_ls_wR_factor_gt 0.0919 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.09593(8) 0.45566(7) 0.31169(7) 0.01814(19) Uani 1 1 d . . . N2 N -0.10075(8) 0.50197(7) 0.18486(7) 0.01809(19) Uani 1 1 d . . . N3 N 0.06092(10) 0.65649(7) 0.27635(8) 0.0251(2) Uani 1 1 d D . . N4 N -0.04233(13) 0.71486(9) 0.32030(11) 0.0251(3) Uani 0.902(3) 1 d PDU A 1 O O -0.01179(10) 0.81880(7) 0.33767(9) 0.0348(3) Uani 0.902(3) 1 d PD A 1 N4' N 0.0297(14) 0.7461(10) 0.3141(10) 0.037(3) Uiso 0.098(3) 1 d PDU A 2 O' O -0.0766(11) 0.7124(9) 0.3700(10) 0.035(3) Uiso 0.098(3) 1 d PDU A 2 C1 C 0.01769(10) 0.54492(8) 0.25812(8) 0.0176(2) Uani 1 1 d . A . C2 C 0.02221(12) 0.35595(9) 0.27501(9) 0.0241(2) Uani 1 1 d . . . H2 H 0.0520 0.2808 0.2996 0.029 Uiso 1 1 calc R . . C3 C -0.09923(11) 0.38421(9) 0.19837(9) 0.0236(2) Uani 1 1 d . . . H3 H -0.1711 0.3326 0.1603 0.028 Uiso 1 1 calc R . . C4 C 0.23531(10) 0.46378(9) 0.40098(9) 0.0197(2) Uani 1 1 d . . . C5 C 0.20553(11) 0.52921(9) 0.51226(9) 0.0230(2) Uani 1 1 d . . . H5A H 0.1677 0.6053 0.4880 0.034 Uiso 1 1 calc R . . H5B H 0.2962 0.5367 0.5698 0.034 Uiso 1 1 calc R . . H5C H 0.1335 0.4876 0.5504 0.034 Uiso 1 1 calc R . . C6 C 0.35015(11) 0.52248(11) 0.33943(10) 0.0283(3) Uani 1 1 d . . . H6A H 0.3687 0.4764 0.2705 0.043 Uiso 1 1 calc R . . H6B H 0.4406 0.5306 0.3971 0.043 Uiso 1 1 calc R . . H6C H 0.3150 0.5982 0.3111 0.043 Uiso 1 1 calc R . . C7 C 0.28506(12) 0.34267(10) 0.43809(10) 0.0298(3) Uani 1 1 d . . . H7A H 0.2112 0.3054 0.4780 0.045 Uiso 1 1 calc R . . H7B H 0.3776 0.3460 0.4939 0.045 Uiso 1 1 calc R . . H7C H 0.2983 0.2989 0.3661 0.045 Uiso 1 1 calc R . . C8 C -0.21489(10) 0.56433(9) 0.09730(9) 0.0204(2) Uani 1 1 d . . . C9 C -0.14721(12) 0.66507(11) 0.04032(11) 0.0337(3) Uani 1 1 d . . . H9A H -0.1218 0.7251 0.1010 0.051 Uiso 1 1 calc R . . H9B H -0.2172 0.6952 -0.0270 0.051 Uiso 1 1 calc R . . H9C H -0.0591 0.6397 0.0103 0.051 Uiso 1 1 calc R . . C10 C -0.33748(11) 0.60123(10) 0.16404(10) 0.0266(2) Uani 1 1 d . . . H10A H -0.3801 0.5337 0.1966 0.040 Uiso 1 1 calc R . . H10B H -0.4127 0.6411 0.1080 0.040 Uiso 1 1 calc R . . H10C H -0.2986 0.6526 0.2304 0.040 Uiso 1 1 calc R . . C11 C -0.27641(12) 0.48103(11) -0.00300(10) 0.0300(3) Uani 1 1 d . . . H11A H -0.1967 0.4505 -0.0411 0.045 Uiso 1 1 calc R . . H11B H -0.3460 0.5211 -0.0637 0.045 Uiso 1 1 calc R . . H11C H -0.3260 0.4181 0.0314 0.045 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0160(4) 0.0200(4) 0.0176(4) 0.0009(3) 0.0001(3) 0.0011(3) N2 0.0158(4) 0.0207(4) 0.0170(4) 0.0011(3) 0.0004(3) 0.0012(3) N3 0.0224(4) 0.0201(4) 0.0305(5) 0.0015(3) -0.0031(3) -0.0003(3) N4 0.0261(6) 0.0186(5) 0.0291(6) -0.0027(4) 0.0004(5) 0.0005(4) O 0.0370(5) 0.0176(5) 0.0459(6) -0.0057(4) -0.0045(4) -0.0001(4) C1 0.0149(4) 0.0207(5) 0.0171(4) 0.0013(3) 0.0026(3) 0.0008(3) C2 0.0271(5) 0.0186(5) 0.0248(5) 0.0006(4) -0.0019(4) -0.0003(4) C3 0.0250(5) 0.0202(5) 0.0239(5) -0.0002(4) -0.0017(4) -0.0029(4) C4 0.0147(4) 0.0256(5) 0.0174(5) 0.0015(4) -0.0014(3) 0.0018(4) C5 0.0205(5) 0.0295(5) 0.0180(5) -0.0002(4) 0.0003(4) 0.0007(4) C6 0.0158(5) 0.0465(7) 0.0224(5) 0.0046(5) 0.0019(4) -0.0013(4) C7 0.0270(5) 0.0285(6) 0.0299(6) 0.0011(4) -0.0070(4) 0.0075(4) C8 0.0151(4) 0.0261(5) 0.0187(5) 0.0026(4) -0.0013(3) 0.0033(4) C9 0.0240(5) 0.0420(7) 0.0329(6) 0.0187(5) -0.0021(4) 0.0000(5) C10 0.0186(5) 0.0343(6) 0.0260(5) -0.0044(4) 0.0011(4) 0.0054(4) C11 0.0279(5) 0.0376(6) 0.0212(5) -0.0055(4) -0.0058(4) 0.0095(5) _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 C1 1.3571(12) . ? N1 C2 1.3823(13) . ? N1 C4 1.5084(12) . ? N2 C1 1.3603(12) . ? N2 C3 1.3864(13) . ? N2 C8 1.5130(12) . ? N3 N4' 1.185(11) . ? N3 N4 1.3350(15) . ? N3 C1 1.3720(13) . ? N4 O 1.2574(14) . ? N4' O' 1.312(13) . ? C2 C3 1.3461(14) . ? C4 C6 1.5244(14) . ? C4 C5 1.5268(14) . ? C4 C7 1.5280(14) . ? C8 C10 1.5226(13) . ? C8 C9 1.5243(15) . ? C8 C11 1.5287(14) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C2 108.26(8) . . ? C1 N1 C4 126.01(8) . . ? C2 N1 C4 125.66(8) . . ? C1 N2 C3 107.95(8) . . ? C1 N2 C8 129.01(8) . . ? C3 N2 C8 122.98(8) . . ? N4' N3 N4 35.2(6) . . ? N4' N3 C1 144.4(6) . . ? N4 N3 C1 109.35(9) . . ? O N4 N3 113.24(12) . . ? N3 N4' O' 98.7(10) . . ? N1 C1 N2 107.91(8) . . ? N1 C1 N3 122.92(9) . . ? N2 C1 N3 129.14(9) . . ? C3 C2 N1 107.92(9) . . ? C2 C3 N2 107.88(9) . . ? N1 C4 C6 108.49(8) . . ? N1 C4 C5 108.99(8) . . ? C6 C4 C5 112.07(9) . . ? N1 C4 C7 108.22(8) . . ? C6 C4 C7 109.76(9) . . ? C5 C4 C7 109.23(8) . . ? N2 C8 C10 108.67(8) . . ? N2 C8 C9 110.59(8) . . ? C10 C8 C9 112.22(9) . . ? N2 C8 C11 108.10(8) . . ? C10 C8 C11 108.75(8) . . ? C9 C8 C11 108.41(9) . . ? 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 N4' N3 N4 O 5.3(10) . . . . ? C1 N3 N4 O -178.89(10) . . . . ? N4 N3 N4' O' 18.8(6) . . . . ? C1 N3 N4' O' 11.9(15) . . . . ? C2 N1 C1 N2 -2.38(11) . . . . ? C4 N1 C1 N2 -179.45(8) . . . . ? C2 N1 C1 N3 179.66(9) . . . . ? C4 N1 C1 N3 2.58(15) . . . . ? C3 N2 C1 N1 3.05(10) . . . . ? C8 N2 C1 N1 -174.22(8) . . . . ? C3 N2 C1 N3 -179.15(10) . . . . ? C8 N2 C1 N3 3.57(16) . . . . ? N4' N3 C1 N1 -117.6(10) . . . . ? N4 N3 C1 N1 -121.73(10) . . . . ? N4' N3 C1 N2 64.9(10) . . . . ? N4 N3 C1 N2 60.77(13) . . . . ? C1 N1 C2 C3 0.77(12) . . . . ? C4 N1 C2 C3 177.86(9) . . . . ? N1 C2 C3 N2 1.11(12) . . . . ? C1 N2 C3 C2 -2.58(11) . . . . ? C8 N2 C3 C2 174.89(9) . . . . ? C1 N1 C4 C6 -61.21(12) . . . . ? C2 N1 C4 C6 122.21(10) . . . . ? C1 N1 C4 C5 61.06(12) . . . . ? C2 N1 C4 C5 -115.52(10) . . . . ? C1 N1 C4 C7 179.75(9) . . . . ? C2 N1 C4 C7 3.17(13) . . . . ? C1 N2 C8 C10 -89.52(11) . . . . ? C3 N2 C8 C10 93.57(11) . . . . ? C1 N2 C8 C9 34.07(13) . . . . ? C3 N2 C8 C9 -142.83(10) . . . . ? C1 N2 C8 C11 152.62(10) . . . . ? C3 N2 C8 C11 -24.29(13) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 75.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.253 _refine_diff_density_min -0.289 _refine_diff_density_rms 0.040 _iucr_refine_instructions_details ; TITL eileen35 in P2(1)/n CELL 1.54184 9.2956 11.7049 11.2144 90.000 99.208 90.000 ZERR 4.00 0.0002 0.0002 0.0002 0.000 0.002 0.000 LATT 1 SYMM 1/2 - X, 1/2 + Y, 1/2 - Z SFAC C H N O UNIT 44 80 16 4 SIZE 0.10 0.05 0.04 TEMP -173 ACTA 150 CONF FMAP 2 PLAN 10 L.S. 8 WGHT 0.049100 0.378200 FVAR 6.61443 0.90202 N1 3 0.095926 0.455656 0.311689 11.00000 0.01599 0.02002 = 0.01758 0.00088 0.00014 0.00105 N2 3 -0.100753 0.501968 0.184856 11.00000 0.01583 0.02073 = 0.01699 0.00106 0.00043 0.00116 SIMU N3 > O' 0.02 0.04 0.9 SAME N3 N4' O' N3 3 0.060925 0.656488 0.276347 11.00000 0.02242 0.02006 = 0.03045 0.00147 -0.00310 -0.00033 PART 1 21 N4 3 -0.042326 0.714860 0.320298 21.00000 0.02612 0.01862 = 0.02915 -0.00274 0.00037 0.00051 O 4 -0.011789 0.818804 0.337666 21.00000 0.03703 0.01762 = 0.04595 -0.00574 -0.00451 -0.00006 PART 2 -21 N4' 3 0.029691 0.746103 0.314140 -21.00000 0.03660 O' 4 -0.076619 0.712432 0.370004 -21.00000 0.03541 PART 0 C1 1 0.017692 0.544919 0.258117 11.00000 0.01491 0.02074 = 0.01706 0.00133 0.00256 0.00078 C2 1 0.022206 0.355947 0.275011 11.00000 0.02708 0.01858 = 0.02477 0.00063 -0.00185 -0.00035 AFIX 43 H2 2 0.051980 0.280759 0.299557 11.00000 -1.20000 AFIX 0 C3 1 -0.099226 0.384213 0.198365 11.00000 0.02498 0.02022 = 0.02385 -0.00023 -0.00175 -0.00294 AFIX 43 H3 2 -0.171133 0.332621 0.160281 11.00000 -1.20000 AFIX 0 C4 1 0.235306 0.463778 0.400984 11.00000 0.01470 0.02563 = 0.01738 0.00153 -0.00143 0.00181 C5 1 0.205530 0.529208 0.512264 11.00000 0.02050 0.02953 = 0.01799 -0.00023 0.00032 0.00069 AFIX 137 H5A 2 0.167731 0.605322 0.488045 11.00000 -1.50000 H5B 2 0.296238 0.536721 0.569757 11.00000 -1.50000 H5C 2 0.133508 0.487578 0.550419 11.00000 -1.50000 AFIX 0 C6 1 0.350145 0.522482 0.339435 11.00000 0.01578 0.04653 = 0.02236 0.00463 0.00189 -0.00135 AFIX 137 H6A 2 0.368692 0.476411 0.270522 11.00000 -1.50000 H6B 2 0.440582 0.530564 0.397146 11.00000 -1.50000 H6C 2 0.314987 0.598210 0.311069 11.00000 -1.50000 AFIX 0 C7 1 0.285065 0.342671 0.438089 11.00000 0.02704 0.02852 = 0.02992 0.00108 -0.00696 0.00753 AFIX 137 H7A 2 0.211211 0.305442 0.478043 11.00000 -1.50000 H7B 2 0.377590 0.346010 0.493870 11.00000 -1.50000 H7C 2 0.298305 0.298891 0.366148 11.00000 -1.50000 AFIX 0 C8 1 -0.214892 0.564329 0.097297 11.00000 0.01514 0.02608 = 0.01869 0.00258 -0.00127 0.00329 C9 1 -0.147205 0.665074 0.040316 11.00000 0.02399 0.04203 = 0.03295 0.01868 -0.00209 0.00002 AFIX 137 H9A 2 -0.121776 0.725077 0.100973 11.00000 -1.50000 H9B 2 -0.217234 0.695203 -0.026978 11.00000 -1.50000 H9C 2 -0.059088 0.639713 0.010317 11.00000 -1.50000 AFIX 0 C10 1 -0.337483 0.601234 0.164038 11.00000 0.01856 0.03430 = 0.02601 -0.00437 0.00112 0.00539 AFIX 137 H10A 2 -0.380102 0.533747 0.196581 11.00000 -1.50000 H10B 2 -0.412671 0.641129 0.108044 11.00000 -1.50000 H10C 2 -0.298578 0.652579 0.230447 11.00000 -1.50000 AFIX 0 C11 1 -0.276406 0.481029 -0.002997 11.00000 0.02791 0.03760 = 0.02123 -0.00548 -0.00583 0.00947 AFIX 137 H11A 2 -0.196689 0.450469 -0.041052 11.00000 -1.50000 H11B 2 -0.345992 0.521087 -0.063674 11.00000 -1.50000 H11C 2 -0.325974 0.418130 0.031438 11.00000 -1.50000 HKLF 4 ; #============================================================================= # end of cif data for "eileen35" (compound 6 - Supp. Mat.) #============================================================================= _database_code_depnum_ccdc_archive 'CCDC 964196'