# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Chi-Chiu Ko' _publ_contact_author_email vinccko@cityu.edu.hk _publ_section_title ; Luminescent Rhenium(I) Complexes With Acetylamino- and Trifluoroacetylamino-Containing Phenanthroline Ligands: Anion-Sensing Study ; loop_ _publ_author_name 'Chi-On Ng' 'Sze-Wing Lai' 'Hua Feng' 'Shek-Man Yiu' 'Chi-Chiu Ko' # Attachment '- 1.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 823826' #TrackingRef '- 1.cif' _audit_creation_date 2011-01-21 _audit_creation_method ; Olex2 1.1 (compiled 2010.09.30 svn.r1450, GUI svn.r3284) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C17 H8 Br F3 N3 O4 Re, C3 H6 O' _chemical_formula_sum 'C20 H14 Br F3 N3 O5 Re' _chemical_formula_weight 699.45 _chemical_melting_point ? 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' 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' Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Re Re -5.2083 5.8923 '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' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 8.7190(3) _cell_length_b 10.9686(6) _cell_length_c 12.2992(6) _cell_angle_alpha 97.534(4) _cell_angle_beta 97.506(4) _cell_angle_gamma 99.618(4) _cell_volume 1135.61(9) _cell_formula_units_Z 2 _cell_measurement_reflns_used 5404 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 71.1746 _cell_measurement_theta_min 3.667 _exptl_absorpt_coefficient_mu 13.093 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_correction_T_min 0.39418 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour yellow _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 2.046 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 664 _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.03 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0193 _diffrn_reflns_av_unetI/netI 0.0183 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 6591 _diffrn_reflns_theta_full 66.99 _diffrn_reflns_theta_max 66.99 _diffrn_reflns_theta_min 3.67 _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 16.127 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega 7.00 33.00 1.0000 16.0000 omega____ theta____ kappa____ phi______ frames - -39.7727 37.0000 -180.0000 26 #__ type_ start__ end____ width___ exp.time_ 2 omega -51.00 -22.00 1.0000 16.0000 omega____ theta____ kappa____ phi______ frames - -39.7727 37.0000 -180.0000 29 #__ type_ start__ end____ width___ exp.time_ 3 omega 17.00 107.00 1.0000 16.0000 omega____ theta____ kappa____ phi______ frames - 39.7727 37.0000 -60.0000 90 #__ type_ start__ end____ width___ exp.time_ 4 omega -31.00 66.00 1.0000 16.0000 omega____ theta____ kappa____ phi______ frames - 39.7727 -37.0000 120.0000 97 #__ type_ start__ end____ width___ exp.time_ 5 omega -26.00 66.00 1.0000 16.0000 omega____ theta____ kappa____ phi______ frames - 39.7727 -37.0000 0.0000 92 #__ type_ start__ end____ width___ exp.time_ 6 omega -84.00 6.00 1.0000 48.0000 omega____ theta____ kappa____ phi______ frames - -64.0000 77.0000 -30.0000 90 #__ type_ start__ end____ width___ exp.time_ 7 omega -78.00 -38.00 1.0000 48.0000 omega____ theta____ kappa____ phi______ frames - -64.0000 50.0000 90.0000 40 #__ type_ start__ end____ width___ exp.time_ 8 omega -140.00 -80.00 1.0000 48.0000 omega____ theta____ kappa____ phi______ frames - -64.0000 179.0000 0.0000 60 #__ type_ start__ end____ width___ exp.time_ 9 omega 96.00 167.00 1.0000 48.0000 omega____ theta____ kappa____ phi______ frames - 109.0296 50.0000 -60.0000 71 #__ type_ start__ end____ width___ exp.time_ 10 omega 59.00 121.00 1.0000 48.0000 omega____ theta____ kappa____ phi______ frames - 109.0296 -50.0000 60.0000 62 #__ type_ start__ end____ width___ exp.time_ 11 omega 86.00 178.00 1.0000 48.0000 omega____ theta____ kappa____ phi______ frames - 109.0296 25.0000 60.0000 92 #__ type_ start__ end____ width___ exp.time_ 12 omega 87.00 114.00 1.0000 48.0000 omega____ theta____ kappa____ phi______ frames - 109.0296 50.0000 -120.0000 27 #__ type_ start__ end____ width___ exp.time_ 13 omega 148.00 178.00 1.0000 48.0000 omega____ theta____ kappa____ phi______ frames - 109.0296 50.0000 -120.0000 30 #__ type_ start__ end____ width___ exp.time_ 14 omega 37.00 67.00 1.0000 48.0000 omega____ theta____ kappa____ phi______ frames - 109.0296 -92.0000 -145.0000 30 #__ type_ start__ end____ width___ exp.time_ 15 omega 39.00 123.00 1.0000 48.0000 omega____ theta____ kappa____ phi______ frames - 109.0296 -50.0000 -150.0000 84 #__ type_ start__ end____ width___ exp.time_ 16 omega 87.00 124.00 1.0000 48.0000 omega____ theta____ kappa____ phi______ frames - 109.0296 50.0000 0.0000 37 #__ type_ start__ end____ width___ exp.time_ 17 omega 96.00 143.00 1.0000 48.0000 omega____ theta____ kappa____ phi______ frames - 109.0296 -25.0000 60.0000 47 #__ type_ start__ end____ width___ exp.time_ 18 omega 44.00 70.00 1.0000 48.0000 omega____ theta____ kappa____ phi______ frames - 109.0296 -25.0000 60.0000 26 #__ type_ start__ end____ width___ exp.time_ 19 omega 39.00 120.00 1.0000 48.0000 omega____ theta____ kappa____ phi______ frames - 109.0296 -50.0000 -30.0000 81 #__ type_ start__ end____ width___ exp.time_ 20 omega 72.00 119.00 1.0000 48.0000 omega____ theta____ kappa____ phi______ frames - 109.0296 -92.0000 -145.0000 47 #__ type_ start__ end____ width___ exp.time_ 21 omega 54.00 144.00 1.0000 48.0000 omega____ theta____ kappa____ phi______ frames - 109.0296 -92.0000 93.0000 90 #__ type_ start__ end____ width___ exp.time_ 22 omega 46.00 114.00 1.0000 48.0000 omega____ theta____ kappa____ phi______ frames - 109.0296 -92.0000 -9.0000 68 ; _diffrn_measurement_device_type 'Gemini S Ultra' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0469785 _diffrn_orient_matrix_UB_12 0.0263862 _diffrn_orient_matrix_UB_13 -0.1185947 _diffrn_orient_matrix_UB_21 -0.055901 _diffrn_orient_matrix_UB_22 0.1190331 _diffrn_orient_matrix_UB_23 0.0477373 _diffrn_orient_matrix_UB_31 0.1660888 _diffrn_orient_matrix_UB_32 0.0770536 _diffrn_orient_matrix_UB_33 0.0043277 _diffrn_radiation_monochromator mirror _diffrn_radiation_source 'Enhance Ultra (Cu) X-ray Source' _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.5418 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 3780 _reflns_number_total 4037 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _refine_diff_density_max 0.972 _refine_diff_density_min -1.013 _refine_diff_density_rms 0.095 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 303 _refine_ls_number_reflns 4037 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0298 _refine_ls_R_factor_gt 0.0278 _refine_ls_restrained_S_all 1.089 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; calc w=1/[\s^2^(Fo^2^)+(0.0443P) ^2^+1.6833P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0781 _refine_ls_wR_factor_ref 0.0791 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 Re1 Re 0.72311(2) 0.48951(2) 0.304703(16) 0.04660(9) Uani 1 1 d . . . Br1 Br 0.63266(6) 0.63385(5) 0.16466(5) 0.05565(14) Uani 1 1 d . . . F1 F 1.0246(5) -0.1482(4) -0.2487(4) 0.0996(13) Uani 1 1 d . . . F2 F 0.9142(7) -0.0265(4) -0.3370(3) 0.1110(16) Uani 1 1 d . . . F3 F 0.7864(5) -0.1356(5) -0.2393(5) 0.133(2) Uani 1 1 d . . . O1 O 0.8160(7) 0.3149(6) 0.4640(5) 0.1035(17) Uani 1 1 d . . . O2 O 0.4022(5) 0.4525(6) 0.3835(4) 0.0882(14) Uani 1 1 d . . . O3 O 0.8466(6) 0.7113(6) 0.4922(5) 0.115(2) Uani 1 1 d . . . O4 O 1.1078(4) 0.0423(4) -0.0876(4) 0.0659(10) Uani 1 1 d . . . O5 O 0.6021(8) 0.0894(8) 0.7100(5) 0.142(3) Uani 1 1 d . . . N1 N 0.6587(4) 0.3407(3) 0.1621(3) 0.0409(8) Uani 1 1 d . . . N2 N 0.9354(4) 0.4968(4) 0.2264(3) 0.0436(8) Uani 1 1 d . . . N3 N 0.8742(5) 0.1096(4) -0.1294(3) 0.0507(9) Uani 1 1 d D . . H3 H 0.788(4) 0.100(5) -0.174(4) 0.061 Uiso 1 1 d D . . C1 C 0.7852(7) 0.3795(6) 0.4028(5) 0.0654(14) Uani 1 1 d . . . C2 C 0.5237(6) 0.4686(6) 0.3555(4) 0.0603(13) Uani 1 1 d . . . C3 C 0.7996(7) 0.6279(7) 0.4239(5) 0.0753(17) Uani 1 1 d . . . C4 C 0.5181(5) 0.2696(4) 0.1268(4) 0.0472(10) Uani 1 1 d . . . H4 H 0.4359 0.2835 0.1651 0.057 Uiso 1 1 calc R . . C5 C 0.4872(6) 0.1759(5) 0.0359(5) 0.0539(11) Uani 1 1 d . . . H5 H 0.3858 0.1297 0.0129 0.065 Uiso 1 1 calc R . . C6 C 0.6076(5) 0.1516(4) -0.0202(4) 0.0493(10) Uani 1 1 d . . . H6 H 0.5894 0.0864 -0.0795 0.059 Uiso 1 1 calc R . . C7 C 0.7582(5) 0.2257(4) 0.0123(4) 0.0416(9) Uani 1 1 d . . . C8 C 0.8935(5) 0.2097(4) -0.0408(4) 0.0450(9) Uani 1 1 d . . . C9 C 1.0336(5) 0.2905(4) -0.0070(4) 0.0458(10) Uani 1 1 d . . . H9 H 1.1184 0.2800 -0.0436 0.055 Uiso 1 1 calc R . . C10 C 1.0532(5) 0.3898(4) 0.0826(4) 0.0427(9) Uani 1 1 d . . . C11 C 1.1932(5) 0.4778(4) 0.1176(4) 0.0490(10) Uani 1 1 d . . . H11 H 1.2803 0.4722 0.0822 0.059 Uiso 1 1 calc R . . C12 C 1.2009(5) 0.5712(5) 0.2033(4) 0.0520(11) Uani 1 1 d . . . H12 H 1.2926 0.6309 0.2257 0.062 Uiso 1 1 calc R . . C13 C 1.0712(5) 0.5776(5) 0.2577(4) 0.0508(11) Uani 1 1 d . . . H13 H 1.0798 0.6404 0.3180 0.061 Uiso 1 1 calc R . . C14 C 0.9265(5) 0.4050(4) 0.1400(4) 0.0402(9) Uani 1 1 d . . . C15 C 0.7781(5) 0.3213(4) 0.1035(3) 0.0391(8) Uani 1 1 d . . . C16 C 0.9812(6) 0.0346(4) -0.1436(4) 0.0499(10) Uani 1 1 d . . . C17 C 0.9251(7) -0.0704(5) -0.2434(5) 0.0643(14) Uani 1 1 d . . . C18 C 0.4851(13) 0.1688(9) 0.5641(8) 0.118(3) Uani 1 1 d . . . H18B H 0.4464 0.2435 0.5870 0.177 Uiso 1 1 calc R . . H18A H 0.4192 0.1227 0.4979 0.177 Uiso 1 1 calc R . . H18C H 0.5909 0.1909 0.5495 0.177 Uiso 1 1 calc R . . C19 C 0.4834(8) 0.0894(7) 0.6545(6) 0.0794(19) Uani 1 1 d . . . C20 C 0.3295(14) 0.0257(11) 0.6674(11) 0.164(6) Uani 1 1 d . . . H20C H 0.3407 -0.0346 0.7165 0.246 Uiso 1 1 calc R . . H20A H 0.2737 -0.0163 0.5963 0.246 Uiso 1 1 calc R . . H20B H 0.2717 0.0856 0.6979 0.246 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 Re1 0.04073(13) 0.06376(15) 0.03462(13) 0.00123(9) 0.00850(8) 0.01085(9) Br1 0.0501(3) 0.0631(3) 0.0595(3) 0.0143(2) 0.0183(2) 0.0156(2) F1 0.112(3) 0.079(2) 0.105(3) -0.022(2) 0.010(3) 0.042(2) F2 0.175(5) 0.099(3) 0.054(2) -0.008(2) 0.000(3) 0.040(3) F3 0.091(3) 0.111(3) 0.163(5) -0.068(3) 0.052(3) -0.035(3) O1 0.099(4) 0.143(5) 0.082(3) 0.048(3) 0.006(3) 0.044(3) O2 0.058(2) 0.157(5) 0.057(2) 0.023(3) 0.027(2) 0.021(3) O3 0.089(3) 0.134(5) 0.093(4) -0.063(4) -0.005(3) 0.012(3) O4 0.050(2) 0.068(2) 0.076(3) -0.0016(19) 0.0070(18) 0.0129(17) O5 0.118(5) 0.208(8) 0.088(4) -0.038(4) -0.033(4) 0.086(5) N1 0.0369(18) 0.0473(19) 0.0393(19) 0.0069(15) 0.0109(14) 0.0060(14) N2 0.0410(19) 0.052(2) 0.0361(19) -0.0011(15) 0.0057(15) 0.0110(15) N3 0.048(2) 0.055(2) 0.046(2) -0.0035(17) 0.0056(17) 0.0130(18) C1 0.058(3) 0.094(4) 0.047(3) 0.015(3) 0.007(2) 0.019(3) C2 0.059(3) 0.094(4) 0.034(2) 0.011(2) 0.016(2) 0.024(3) C3 0.057(3) 0.110(5) 0.057(3) -0.002(3) 0.012(3) 0.018(3) C4 0.035(2) 0.055(3) 0.053(3) 0.011(2) 0.0142(19) 0.0056(18) C5 0.040(2) 0.052(3) 0.065(3) 0.005(2) 0.006(2) -0.0001(19) C6 0.045(2) 0.046(2) 0.052(3) 0.004(2) 0.001(2) 0.0024(19) C7 0.038(2) 0.043(2) 0.042(2) 0.0061(18) 0.0040(17) 0.0053(17) C8 0.046(2) 0.048(2) 0.042(2) 0.0047(18) 0.0080(19) 0.0100(18) C9 0.042(2) 0.053(2) 0.045(2) 0.0040(19) 0.0145(19) 0.0127(19) C10 0.037(2) 0.048(2) 0.044(2) 0.0097(18) 0.0071(17) 0.0079(17) C11 0.033(2) 0.053(2) 0.062(3) 0.011(2) 0.0082(19) 0.0057(18) C12 0.035(2) 0.056(3) 0.060(3) 0.002(2) 0.001(2) 0.0028(19) C13 0.039(2) 0.056(3) 0.050(3) -0.005(2) 0.0003(19) 0.0030(19) C14 0.033(2) 0.047(2) 0.040(2) 0.0072(17) 0.0038(16) 0.0055(16) C15 0.035(2) 0.043(2) 0.038(2) 0.0043(17) 0.0044(16) 0.0070(16) C16 0.048(3) 0.051(2) 0.051(3) 0.005(2) 0.016(2) 0.008(2) C17 0.065(3) 0.065(3) 0.062(3) -0.007(3) 0.017(3) 0.015(3) C18 0.141(8) 0.116(7) 0.102(7) 0.001(5) 0.032(6) 0.040(6) C19 0.071(4) 0.092(4) 0.065(4) -0.027(3) 0.004(3) 0.022(3) C20 0.151(10) 0.136(9) 0.183(12) -0.029(9) 0.077(9) -0.030(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 Re1 Br1 2.6215(6) . ? Re1 N1 2.177(4) . ? Re1 N2 2.190(4) . ? Re1 C1 1.906(6) . ? Re1 C2 1.912(5) . ? Re1 C3 1.929(7) . ? F1 C17 1.316(7) . ? F2 C17 1.303(8) . ? F3 C17 1.308(7) . ? O1 C1 1.137(7) . ? O2 C2 1.149(7) . ? O3 C3 1.138(8) . ? O4 C16 1.206(6) . ? O5 C19 1.164(8) . ? N1 C4 1.324(6) . ? N1 C15 1.371(5) . ? N2 C13 1.333(6) . ? N2 C14 1.350(6) . ? N3 H3 0.85(2) . ? N3 C8 1.413(6) . ? N3 C16 1.356(6) . ? C4 H4 0.9300 . ? C4 C5 1.381(7) . ? C5 H5 0.9300 . ? C5 C6 1.373(7) . ? C6 H6 0.9300 . ? C6 C7 1.402(6) . ? C7 C8 1.446(6) . ? C7 C15 1.402(6) . ? C8 C9 1.363(6) . ? C9 H9 0.9300 . ? C9 C10 1.416(6) . ? C10 C11 1.403(6) . ? C10 C14 1.408(6) . ? C11 H11 0.9300 . ? C11 C12 1.356(7) . ? C12 H12 0.9300 . ? C12 C13 1.394(7) . ? C13 H13 0.9300 . ? C14 C15 1.436(6) . ? C16 C17 1.535(7) . ? C18 H18B 0.9600 . ? C18 H18A 0.9600 . ? C18 H18C 0.9600 . ? C18 C19 1.500(12) . ? C19 C20 1.444(12) . ? C20 H20C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? 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 C17 C16 111.0(5) . . ? F2 C17 F1 106.8(5) . . ? F2 C17 F3 106.9(6) . . ? F2 C17 C16 111.8(5) . . ? F3 C17 F1 107.9(5) . . ? F3 C17 C16 112.3(5) . . ? O1 C1 Re1 176.5(6) . . ? O2 C2 Re1 177.8(6) . . ? O3 C3 Re1 178.1(7) . . ? O4 C16 N3 127.5(5) . . ? O4 C16 C17 120.0(5) . . ? O5 C19 C18 118.1(9) . . ? O5 C19 C20 126.5(11) . . ? N1 Re1 Br1 84.95(9) . . ? N1 Re1 N2 75.47(13) . . ? N1 C4 H4 118.3 . . ? N1 C4 C5 123.4(4) . . ? N1 C15 C7 122.5(4) . . ? N1 C15 C14 116.4(4) . . ? N2 Re1 Br1 86.18(10) . . ? N2 C13 C12 122.3(4) . . ? N2 C13 H13 118.9 . . ? N2 C14 C10 123.4(4) . . ? N2 C14 C15 117.7(4) . . ? N3 C8 C7 117.8(4) . . ? N3 C16 C17 112.5(4) . . ? C1 Re1 Br1 177.97(19) . . ? C1 Re1 N1 93.1(2) . . ? C1 Re1 N2 93.8(2) . . ? C1 Re1 C2 88.0(2) . . ? C1 Re1 C3 88.8(3) . . ? C2 Re1 Br1 91.68(16) . . ? C2 Re1 N1 97.04(19) . . ? C2 Re1 N2 172.35(18) . . ? C2 Re1 C3 88.9(2) . . ? C3 Re1 Br1 93.2(2) . . ? C3 Re1 N1 173.8(2) . . ? C3 Re1 N2 98.6(2) . . ? C4 N1 Re1 126.9(3) . . ? C4 N1 C15 117.8(4) . . ? C4 C5 H5 120.4 . . ? C5 C4 H4 118.3 . . ? C5 C6 H6 120.1 . . ? C5 C6 C7 119.7(4) . . ? C6 C5 C4 119.3(4) . . ? C6 C5 H5 120.4 . . ? C6 C7 C8 124.6(4) . . ? C6 C7 C15 117.2(4) . . ? C7 C6 H6 120.1 . . ? C7 C15 C14 121.1(4) . . ? C8 N3 H3 113(4) . . ? C8 C9 H9 119.2 . . ? C8 C9 C10 121.7(4) . . ? C9 C8 N3 121.7(4) . . ? C9 C8 C7 120.5(4) . . ? C10 C9 H9 119.2 . . ? C10 C11 H11 120.2 . . ? C10 C14 C15 118.9(4) . . ? C11 C10 C9 123.6(4) . . ? C11 C10 C14 116.8(4) . . ? C11 C12 H12 120.0 . . ? C11 C12 C13 120.0(4) . . ? C12 C11 C10 119.6(4) . . ? C12 C11 H11 120.2 . . ? C12 C13 H13 118.9 . . ? C13 N2 Re1 127.2(3) . . ? C13 N2 C14 117.9(4) . . ? C13 C12 H12 120.0 . . ? C14 N2 Re1 114.8(3) . . ? C14 C10 C9 119.6(4) . . ? C15 N1 Re1 115.2(3) . . ? C15 C7 C8 118.1(4) . . ? C16 N3 H3 123(4) . . ? C16 N3 C8 123.9(4) . . ? H18B C18 H18A 109.5 . . ? H18B C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? C19 C18 H18B 109.5 . . ? C19 C18 H18A 109.5 . . ? C19 C18 H18C 109.5 . . ? C19 C20 H20C 109.5 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? C20 C19 C18 115.2(9) . . ? H20C C20 H20A 109.5 . . ? H20C C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H3 O5 0.85(2) 1.99(2) 2.839(7) 173(6) 1_554 # Attachment '- 2.cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 823827' #TrackingRef '- 2.cif' _audit_creation_date 2011-04-29 _audit_creation_method ; Olex2 1.1 (compiled 2011.02.15 svn.r1672, GUI svn.r3494) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C18 H8 F3 N4 O4 Re, C3 H6 O' _chemical_formula_sum 'C21 H14 F3 N4 O5 Re' _chemical_formula_weight 645.56 _chemical_melting_point ? _chemical_oxdiff_formula 'C11 H10 S O2' 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' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Re Re -5.2083 5.8923 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 9.8448(4) _cell_length_b 11.4164(4) _cell_length_c 11.4220(4) _cell_angle_alpha 91.653(3) _cell_angle_beta 103.786(3) _cell_angle_gamma 113.694(3) _cell_volume 1130.40(7) _cell_formula_units_Z 2 _cell_measurement_reflns_used 7158 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 71.5537 _cell_measurement_theta_min 4.0215 _exptl_absorpt_coefficient_mu 11.112 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.31800 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour yellow _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.897 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 620 _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0218 _diffrn_reflns_av_unetI/netI 0.0226 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 6993 _diffrn_reflns_theta_full 66.99 _diffrn_reflns_theta_max 66.99 _diffrn_reflns_theta_min 4.02 _diffrn_ambient_temperature 173.0 _diffrn_detector_area_resol_mean 16.1270 _diffrn_measured_fraction_theta_full 0.990 _diffrn_measured_fraction_theta_max 0.990 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -66.00 5.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 -37.0000 150.0000 71 #__ type_ start__ end____ width___ exp.time_ 2 omega 18.00 46.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 37.0000 -30.0000 28 #__ type_ start__ end____ width___ exp.time_ 3 omega -24.00 11.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 37.0000 -30.0000 35 #__ type_ start__ end____ width___ exp.time_ 4 omega -112.00 -24.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - -55.0000 125.0000 -60.0000 88 #__ type_ start__ end____ width___ exp.time_ 5 omega -28.00 17.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - -55.0000 37.0000 -30.0000 45 #__ type_ start__ end____ width___ exp.time_ 6 omega -76.00 -27.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - -55.0000 125.0000 60.0000 49 #__ type_ start__ end____ width___ exp.time_ 7 omega 81.00 107.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - 55.0000 125.0000 -120.0000 26 #__ type_ start__ end____ width___ exp.time_ 8 omega 31.00 125.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - 55.0000 77.0000 -180.0000 94 #__ type_ start__ end____ width___ exp.time_ 9 omega 83.00 118.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - 55.0000 111.0000 111.0000 35 #__ type_ start__ end____ width___ exp.time_ 10 omega 92.00 126.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - 55.0000 125.0000 -180.0000 34 #__ type_ start__ end____ width___ exp.time_ 11 omega 74.00 101.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - 55.0000 125.0000 -150.0000 27 #__ type_ start__ end____ width___ exp.time_ 12 omega 17.00 71.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - 55.0000 -37.0000 -180.0000 54 #__ type_ start__ end____ width___ exp.time_ 13 omega -70.00 -29.00 1.0000 24.0000 omega____ theta____ kappa____ phi______ frames - -64.0000 25.0000 -120.0000 41 #__ type_ start__ end____ width___ exp.time_ 14 omega 43.00 69.00 1.0000 24.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -25.0000 90.0000 26 #__ type_ start__ end____ width___ exp.time_ 15 omega 40.00 69.00 1.0000 24.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -50.0000 150.0000 29 #__ type_ start__ end____ width___ exp.time_ 16 omega 121.00 164.00 1.0000 24.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 50.0000 -120.0000 43 #__ type_ start__ end____ width___ exp.time_ 17 omega 45.00 72.00 1.0000 24.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -25.0000 60.0000 27 #__ type_ start__ end____ width___ exp.time_ 18 omega 39.00 66.00 1.0000 24.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -25.0000 -180.0000 27 #__ type_ start__ end____ width___ exp.time_ 19 omega 38.00 72.00 1.0000 24.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -25.0000 -60.0000 34 #__ type_ start__ end____ width___ exp.time_ 20 omega 122.00 146.00 1.0000 24.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -88.0000 165.0000 24 #__ type_ start__ end____ width___ exp.time_ 21 omega 38.00 72.00 1.0000 24.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -25.0000 150.0000 34 #__ type_ start__ end____ width___ exp.time_ 22 omega 48.00 79.00 1.0000 24.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -50.0000 -90.0000 31 #__ type_ start__ end____ width___ exp.time_ 23 omega 37.00 62.00 1.0000 24.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -25.0000 0.0000 25 #__ type_ start__ end____ width___ exp.time_ 24 omega 39.00 67.00 1.0000 24.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -25.0000 -120.0000 28 #__ type_ start__ end____ width___ exp.time_ 25 omega 76.00 146.00 1.0000 24.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -88.0000 11.0000 70 #__ type_ start__ end____ width___ exp.time_ 26 omega 55.00 81.00 1.0000 24.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -50.0000 30.0000 26 #__ type_ start__ end____ width___ exp.time_ 27 omega 47.00 75.00 1.0000 24.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -50.0000 -180.0000 28 #__ type_ start__ end____ width___ exp.time_ 28 omega 96.00 137.00 1.0000 24.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 50.0000 -180.0000 41 #__ type_ start__ end____ width___ exp.time_ 29 omega 91.00 116.00 1.0000 24.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 50.0000 120.0000 25 #__ type_ start__ end____ width___ exp.time_ 30 omega 125.00 171.00 1.0000 24.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 50.0000 120.0000 46 #__ type_ start__ end____ width___ exp.time_ 31 omega 51.00 83.00 1.0000 24.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -50.0000 0.0000 32 #__ type_ start__ end____ width___ exp.time_ 32 omega 38.00 72.00 1.0000 24.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -25.0000 -150.0000 34 #__ type_ start__ end____ width___ exp.time_ 33 omega 140.00 175.00 1.0000 24.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 50.0000 -180.0000 35 #__ type_ start__ end____ width___ exp.time_ 34 omega 41.00 69.00 1.0000 24.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -88.0000 11.0000 28 #__ type_ start__ end____ width___ exp.time_ 35 omega 45.00 110.00 1.0000 24.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -88.0000 165.0000 65 #__ type_ start__ end____ width___ exp.time_ 36 omega 40.00 146.00 1.0000 24.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -88.0000 -87.0000 106 ; _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.1155125000 _diffrn_orient_matrix_UB_12 -0.0548433000 _diffrn_orient_matrix_UB_13 0.0592678000 _diffrn_orient_matrix_UB_21 0.0292316000 _diffrn_orient_matrix_UB_22 -0.0197150000 _diffrn_orient_matrix_UB_23 -0.1241761000 _diffrn_orient_matrix_UB_31 0.1317482000 _diffrn_orient_matrix_UB_32 0.1369492000 _diffrn_orient_matrix_UB_33 0.0272165000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.5418 _diffrn_source 'Enhance Ultra (Cu) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 3944 _reflns_number_total 3984 _reflns_odcompleteness_completeness 98.91 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 68.13 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _refine_diff_density_max 2.056 _refine_diff_density_min -1.470 _refine_diff_density_rms 0.158 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.175 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 336 _refine_ls_number_reflns 3984 _refine_ls_number_restraints 36 _refine_ls_R_factor_all 0.0286 _refine_ls_R_factor_gt 0.0283 _refine_ls_restrained_S_all 1.179 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0560P)^2^+0.6340P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0789 _refine_ls_wR_factor_ref 0.0791 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 Re1 Re 0.383999(15) 0.269876(13) 0.266923(12) 0.02083(9) Uani 1 1 d . . . F1 F 1.311(2) 0.3257(15) 0.7612(19) 0.066(4) Uani 0.50 1 d PU A 2 F1A F 1.315(2) 0.3791(16) 0.7716(19) 0.074(5) Uani 0.50 1 d PU A 1 F2 F 1.259(3) 0.374(2) 0.9207(17) 0.069(6) Uani 0.50 1 d PU A 2 F2A F 1.240(2) 0.349(2) 0.9310(13) 0.054(4) Uani 0.50 1 d PU A 1 F3 F 1.212(2) 0.1815(19) 0.8595(16) 0.072(5) Uani 0.50 1 d PU A 2 F3A F 1.233(2) 0.1914(19) 0.8229(18) 0.093(6) Uani 0.50 1 d PU A 1 O1 O 0.5365(5) 0.3208(5) 0.0545(3) 0.0519(10) Uani 1 1 d . . . O2 O 0.3487(4) 0.5240(3) 0.2348(4) 0.0445(8) Uani 1 1 d . . . O3 O 0.0674(4) 0.1268(4) 0.0829(4) 0.0559(10) Uani 1 1 d . . . O4 O 0.9566(3) 0.2731(3) 0.8010(3) 0.0370(7) Uani 1 1 d . . . O5 O 0.8454(5) 0.3009(5) 0.2553(3) 0.0635(12) Uani 1 1 d . . . N1 N 0.6035(4) 0.3484(3) 0.4089(3) 0.0206(6) Uani 1 1 d . . . N2 N 0.4381(4) 0.1039(3) 0.3007(3) 0.0214(6) Uani 1 1 d . . . N3 N 1.0179(4) 0.2371(3) 0.6279(3) 0.0230(7) Uani 1 1 d . . . H3 H 1.0933 0.2394 0.5981 0.028 Uiso 1 1 calc R . . N4 N 0.2146(5) 0.2133(4) 0.4869(4) 0.0297(8) Uani 1 1 d . . . C1 C 0.4839(5) 0.3016(5) 0.1342(4) 0.0326(10) Uani 1 1 d . . . C2 C 0.3613(5) 0.4284(4) 0.2484(4) 0.0281(9) Uani 1 1 d . . . C3 C 0.1866(5) 0.1800(5) 0.1506(4) 0.0334(10) Uani 1 1 d . . . C4 C 0.6808(4) 0.4698(4) 0.4643(3) 0.0235(7) Uani 1 1 d . . . H4 H 0.6380 0.5301 0.4435 0.028 Uiso 1 1 calc R . . C5 C 0.8217(4) 0.5112(4) 0.5513(4) 0.0253(8) Uani 1 1 d . . . H5 H 0.8732 0.5985 0.5894 0.030 Uiso 1 1 calc R . . C6 C 0.8866(4) 0.4269(4) 0.5824(3) 0.0224(7) Uani 1 1 d . . . H6 H 0.9834 0.4550 0.6415 0.027 Uiso 1 1 calc R . . C7 C 0.8085(4) 0.2984(3) 0.5260(3) 0.0196(7) Uani 1 1 d . . . C8 C 0.8680(4) 0.2017(4) 0.5469(3) 0.0208(7) Uani 1 1 d . . . C9 C 0.7877(4) 0.0790(4) 0.4878(3) 0.0238(7) Uani 1 1 d . . . H9 H 0.8307 0.0180 0.5024 0.029 Uiso 1 1 calc R . . C10 C 0.6395(4) 0.0408(4) 0.4042(3) 0.0221(7) Uani 1 1 d . . . C11 C 0.5476(5) -0.0874(4) 0.3453(4) 0.0263(8) Uani 1 1 d . . . H11 H 0.5839 -0.1527 0.3594 0.032 Uiso 1 1 calc R . . C12 C 0.4055(5) -0.1159(4) 0.2677(4) 0.0278(8) Uani 1 1 d . . . H12 H 0.3418 -0.2015 0.2277 0.033 Uiso 1 1 calc R . . C13 C 0.3546(5) -0.0183(4) 0.2477(4) 0.0271(8) Uani 1 1 d . . . H13 H 0.2556 -0.0400 0.1938 0.033 Uiso 1 1 calc R . . C14 C 0.5793(4) 0.1324(3) 0.3809(3) 0.0188(7) Uani 1 1 d . . . C15 C 0.6656(4) 0.2624(3) 0.4406(3) 0.0190(7) Uani 1 1 d . . . C16 C 1.0461(4) 0.2669(4) 0.7481(4) 0.0261(8) Uani 1 1 d . A . C17 C 1.2103(5) 0.2927(5) 0.8214(4) 0.0374(10) Uani 1 1 d . . . C18 C 0.2742(5) 0.2318(4) 0.4107(4) 0.0245(8) Uani 1 1 d . . . C19 C 0.9045(7) 0.3616(6) 0.0726(5) 0.0561(14) Uani 1 1 d . . . H19A H 0.8259 0.3757 0.0114 0.084 Uiso 1 1 calc R . . H19B H 0.9608 0.3277 0.0316 0.084 Uiso 1 1 calc R . . H19C H 0.9766 0.4436 0.1239 0.084 Uiso 1 1 calc R . . C20 C 0.8285(5) 0.2666(5) 0.1498(4) 0.0406(11) Uani 1 1 d . . . C21 C 0.7250(7) 0.1279(6) 0.0908(5) 0.0551(14) Uani 1 1 d . . . H21A H 0.6895 0.0754 0.1530 0.083 Uiso 1 1 calc R . . H21B H 0.7829 0.0933 0.0528 0.083 Uiso 1 1 calc R . . H21C H 0.6357 0.1258 0.0287 0.083 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Re1 0.01906(12) 0.02590(13) 0.02075(12) 0.00545(8) 0.00519(8) 0.01265(9) F1 0.025(5) 0.122(12) 0.046(5) 0.015(8) 0.008(4) 0.028(8) F1A 0.028(5) 0.107(10) 0.048(6) 0.032(8) 0.003(4) -0.008(7) F2 0.055(8) 0.071(7) 0.064(10) -0.028(7) -0.008(6) 0.027(6) F2A 0.032(5) 0.104(11) 0.014(4) 0.011(5) -0.005(3) 0.023(6) F3 0.064(6) 0.062(6) 0.081(8) 0.034(6) -0.004(5) 0.030(5) F3A 0.079(9) 0.094(11) 0.112(12) -0.019(8) -0.030(8) 0.076(9) O1 0.049(2) 0.093(3) 0.0355(19) 0.0240(19) 0.0231(17) 0.044(2) O2 0.048(2) 0.0399(19) 0.062(2) 0.0241(17) 0.0231(17) 0.0295(17) O3 0.0334(19) 0.060(2) 0.059(2) -0.0078(19) -0.0120(17) 0.0187(18) O4 0.0293(15) 0.058(2) 0.0245(14) 0.0051(13) 0.0098(12) 0.0182(14) O5 0.052(2) 0.080(3) 0.0323(19) -0.0045(18) 0.0163(16) -0.001(2) N1 0.0207(15) 0.0238(16) 0.0204(15) 0.0055(12) 0.0072(12) 0.0114(13) N2 0.0224(16) 0.0223(16) 0.0195(15) -0.0006(12) 0.0076(12) 0.0085(13) N3 0.0203(16) 0.0294(17) 0.0228(16) 0.0060(13) 0.0053(13) 0.0142(14) N4 0.037(2) 0.0269(18) 0.039(2) 0.0126(15) 0.0194(17) 0.0219(16) C1 0.029(2) 0.052(3) 0.027(2) 0.0103(19) 0.0079(18) 0.026(2) C2 0.024(2) 0.033(2) 0.032(2) 0.0078(17) 0.0093(16) 0.0159(17) C3 0.026(2) 0.041(2) 0.034(2) 0.0038(19) 0.0029(18) 0.0177(19) C4 0.0245(18) 0.0225(19) 0.0281(18) 0.0047(15) 0.0080(15) 0.0140(16) C5 0.0254(18) 0.0208(18) 0.0276(19) 0.0007(14) 0.0068(15) 0.0082(15) C6 0.0205(17) 0.0258(19) 0.0215(17) 0.0049(14) 0.0065(14) 0.0098(15) C7 0.0222(17) 0.0237(18) 0.0192(16) 0.0071(13) 0.0105(13) 0.0129(15) C8 0.0211(17) 0.0263(18) 0.0189(17) 0.0065(14) 0.0074(14) 0.0125(15) C9 0.0272(19) 0.0264(19) 0.0256(18) 0.0086(15) 0.0096(15) 0.0175(16) C10 0.0246(18) 0.0232(18) 0.0219(17) 0.0051(14) 0.0091(14) 0.0117(15) C11 0.031(2) 0.0222(19) 0.0289(19) 0.0025(15) 0.0073(16) 0.0146(17) C12 0.0278(19) 0.0219(18) 0.0299(19) -0.0005(15) 0.0063(16) 0.0078(16) C13 0.0230(19) 0.029(2) 0.0254(19) 0.0001(16) 0.0065(15) 0.0079(16) C14 0.0181(16) 0.0237(18) 0.0177(15) 0.0043(13) 0.0077(13) 0.0100(14) C15 0.0220(17) 0.0220(17) 0.0183(16) 0.0053(13) 0.0100(13) 0.0118(14) C16 0.0228(18) 0.030(2) 0.0234(18) 0.0078(15) 0.0048(15) 0.0102(16) C17 0.028(2) 0.056(3) 0.025(2) 0.0052(19) 0.0029(17) 0.017(2) C18 0.027(2) 0.025(2) 0.028(2) 0.0068(16) 0.0096(17) 0.0169(17) C19 0.063(3) 0.065(4) 0.047(3) 0.012(3) 0.033(3) 0.023(3) C20 0.031(2) 0.062(3) 0.027(2) 0.002(2) 0.0090(17) 0.017(2) C21 0.049(3) 0.061(3) 0.049(3) -0.003(3) 0.015(2) 0.016(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Re1 N1 2.189(3) . ? Re1 N2 2.186(3) . ? Re1 C1 1.962(4) . ? Re1 C2 1.922(4) . ? Re1 C3 1.919(4) . ? Re1 C18 2.137(4) . ? F1 C17 1.280(19) . ? F1A C17 1.360(19) . ? F2 C17 1.301(19) . ? F2A C17 1.300(17) . ? F3 C17 1.358(19) . ? F3A C17 1.264(18) . ? O1 C1 1.136(6) . ? O2 C2 1.157(6) . ? O3 C3 1.145(6) . ? O4 C16 1.204(5) . ? O5 C20 1.208(6) . ? N1 C4 1.331(5) . ? N1 C15 1.366(5) . ? N2 C13 1.334(5) . ? N2 C14 1.375(5) . ? N3 H3 0.8800 . ? N3 C8 1.430(5) . ? N3 C16 1.338(5) . ? N4 C18 1.140(6) . ? C4 H4 0.9500 . ? C4 C5 1.387(6) . ? C5 H5 0.9500 . ? C5 C6 1.367(5) . ? C6 H6 0.9500 . ? C6 C7 1.400(5) . ? C7 C8 1.446(5) . ? C7 C15 1.399(5) . ? C8 C9 1.358(6) . ? C9 H9 0.9500 . ? C9 C10 1.425(5) . ? C10 C11 1.415(5) . ? C10 C14 1.398(5) . ? C11 H11 0.9500 . ? C11 C12 1.370(6) . ? C12 H12 0.9500 . ? C12 C13 1.397(6) . ? C13 H13 0.9500 . ? C14 C15 1.429(5) . ? C16 C17 1.536(6) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C19 C20 1.494(7) . ? C20 C21 1.521(8) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Re1 N1 75.39(12) . . ? C1 Re1 N1 93.37(16) . . ? C1 Re1 N2 90.80(16) . . ? C1 Re1 C18 178.99(15) . . ? C2 Re1 N1 97.91(15) . . ? C2 Re1 N2 173.15(14) . . ? C2 Re1 C1 88.13(19) . . ? C2 Re1 C18 92.80(16) . . ? C3 Re1 N1 172.50(16) . . ? C3 Re1 N2 97.90(16) . . ? C3 Re1 C1 90.0(2) . . ? C3 Re1 C2 88.86(19) . . ? C3 Re1 C18 89.58(19) . . ? C18 Re1 N1 86.89(14) . . ? C18 Re1 N2 88.32(13) . . ? C4 N1 Re1 126.5(3) . . ? C4 N1 C15 118.3(3) . . ? C15 N1 Re1 115.2(2) . . ? C13 N2 Re1 127.6(3) . . ? C13 N2 C14 117.3(3) . . ? C14 N2 Re1 115.0(2) . . ? C8 N3 H3 119.2 . . ? C16 N3 H3 119.2 . . ? C16 N3 C8 121.6(3) . . ? O1 C1 Re1 177.1(4) . . ? O2 C2 Re1 178.3(4) . . ? O3 C3 Re1 178.6(4) . . ? N1 C4 H4 118.9 . . ? N1 C4 C5 122.2(3) . . ? C5 C4 H4 118.9 . . ? C4 C5 H5 119.9 . . ? C6 C5 C4 120.2(4) . . ? C6 C5 H5 119.9 . . ? C5 C6 H6 120.4 . . ? C5 C6 C7 119.1(3) . . ? C7 C6 H6 120.4 . . ? C6 C7 C8 124.3(3) . . ? C15 C7 C6 117.8(3) . . ? C15 C7 C8 117.8(3) . . ? N3 C8 C7 119.3(3) . . ? C9 C8 N3 119.0(3) . . ? C9 C8 C7 121.6(3) . . ? C8 C9 H9 119.7 . . ? C8 C9 C10 120.7(3) . . ? C10 C9 H9 119.7 . . ? C11 C10 C9 122.9(3) . . ? C14 C10 C9 119.1(3) . . ? C14 C10 C11 118.0(3) . . ? C10 C11 H11 120.5 . . ? C12 C11 C10 118.9(4) . . ? C12 C11 H11 120.5 . . ? C11 C12 H12 120.2 . . ? C11 C12 C13 119.6(4) . . ? C13 C12 H12 120.2 . . ? N2 C13 C12 123.3(4) . . ? N2 C13 H13 118.3 . . ? C12 C13 H13 118.3 . . ? N2 C14 C10 122.8(3) . . ? N2 C14 C15 117.0(3) . . ? C10 C14 C15 120.2(3) . . ? N1 C15 C7 122.4(3) . . ? N1 C15 C14 117.1(3) . . ? C7 C15 C14 120.5(3) . . ? O4 C16 N3 126.6(4) . . ? O4 C16 C17 119.2(4) . . ? N3 C16 C17 114.2(3) . . ? F1 C17 F1A 26.2(10) . . ? F1 C17 F2 110.3(14) . . ? F1 C17 F2A 121.7(13) . . ? F1 C17 F3 102.9(12) . . ? F1 C17 C16 115.2(9) . . ? F1A C17 C16 109.8(9) . . ? F2 C17 F1A 91.3(13) . . ? F2 C17 F3 105.0(13) . . ? F2 C17 C16 112.9(11) . . ? F2A C17 F1A 104.8(13) . . ? F2A C17 F2 14.0(17) . . ? F2A C17 F3 93.7(13) . . ? F2A C17 C16 110.5(9) . . ? F3 C17 F1A 126.7(12) . . ? F3 C17 C16 109.5(10) . . ? F3A C17 F1 82.4(12) . . ? F3A C17 F1A 107.7(13) . . ? F3A C17 F2 120.1(13) . . ? F3A C17 F2A 111.4(13) . . ? F3A C17 F3 21.9(15) . . ? F3A C17 C16 112.4(10) . . ? N4 C18 Re1 178.6(3) . . ? H19A C19 H19B 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C20 C19 H19A 109.5 . . ? C20 C19 H19B 109.5 . . ? C20 C19 H19C 109.5 . . ? O5 C20 C19 120.4(5) . . ? O5 C20 C21 121.2(5) . . ? C19 C20 C21 118.3(4) . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21B 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? # Attachment '- 3.cif' data_3 _database_code_depnum_ccdc_archive 'CCDC 823828' #TrackingRef '- 3.cif' _audit_creation_date 2011-01-21 _audit_creation_method ; Olex2 1.1 (compiled 2010.09.30 svn.r1450, GUI svn.r3284) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C17 H11 Br N3 O4 Re, C3 H6 O' _chemical_formula_sum 'C20 H17 Br N3 O5 Re' _chemical_formula_weight 645.48 _chemical_melting_point ? 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' 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Re Re -1.0185 7.2310 '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' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 7.4454(2) _cell_length_b 12.9411(2) _cell_length_c 13.0901(3) _cell_angle_alpha 118.902(2) _cell_angle_beta 99.420(2) _cell_angle_gamma 93.226(2) _cell_volume 1075.80(4) _cell_formula_units_Z 2 _cell_measurement_reflns_used 17671 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 37.3832 _cell_measurement_theta_min 2.9888 _exptl_absorpt_coefficient_mu 7.541 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_correction_T_min 0.25298 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour yellow _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.993 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description irregular _exptl_crystal_F_000 616 _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.12 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0245 _diffrn_reflns_av_unetI/netI 0.0191 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 14101 _diffrn_reflns_theta_full 25.04 _diffrn_reflns_theta_max 25.04 _diffrn_reflns_theta_min 2.99 _diffrn_ambient_temperature 173.0 _diffrn_detector_area_resol_mean 16.127 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -67.00 -3.00 1.0000 32.0000 omega____ theta____ kappa____ phi______ frames - -37.8894 77.0000 90.0000 64 #__ type_ start__ end____ width___ exp.time_ 2 omega -67.00 -37.00 1.0000 32.0000 omega____ theta____ kappa____ phi______ frames - -37.8894 77.0000 -150.0000 30 #__ type_ start__ end____ width___ exp.time_ 3 omega -88.00 -27.00 1.0000 32.0000 omega____ theta____ kappa____ phi______ frames - -37.8894 -51.0000 -99.0000 61 #__ type_ start__ end____ width___ exp.time_ 4 omega -89.00 -24.00 1.0000 32.0000 omega____ theta____ kappa____ phi______ frames - -37.8894 -37.0000 -60.0000 65 #__ type_ start__ end____ width___ exp.time_ 5 omega -25.00 30.00 1.0000 32.0000 omega____ theta____ kappa____ phi______ frames - -37.8894 77.0000 -150.0000 55 #__ type_ start__ end____ width___ exp.time_ 6 omega 18.00 100.00 1.0000 32.0000 omega____ theta____ kappa____ phi______ frames - 38.5144 77.0000 120.0000 82 #__ type_ start__ end____ width___ exp.time_ 7 omega -4.00 22.00 1.0000 32.0000 omega____ theta____ kappa____ phi______ frames - 38.5144 103.0000 87.0000 26 #__ type_ start__ end____ width___ exp.time_ 8 omega 20.00 57.00 1.0000 32.0000 omega____ theta____ kappa____ phi______ frames - 38.5144 37.0000 -120.0000 37 #__ type_ start__ end____ width___ exp.time_ 9 omega -31.00 20.00 1.0000 32.0000 omega____ theta____ kappa____ phi______ frames - 38.5144 -37.0000 0.0000 51 #__ type_ start__ end____ width___ exp.time_ 10 omega 42.00 88.00 1.0000 32.0000 omega____ theta____ kappa____ phi______ frames - 38.5144 -133.0000 -65.0000 46 #__ type_ start__ end____ width___ exp.time_ 11 omega 3.00 39.00 1.0000 32.0000 omega____ theta____ kappa____ phi______ frames - 38.5144 87.0000 10.0000 36 #__ type_ start__ end____ width___ exp.time_ 12 omega -10.00 56.00 1.0000 32.0000 omega____ theta____ kappa____ phi______ frames - 38.5144 0.0000 -180.0000 66 #__ type_ start__ end____ width___ exp.time_ 13 omega -108.00 -16.00 1.0000 32.0000 omega____ theta____ kappa____ phi______ frames - -37.8894 -49.0000 13.0000 92 #__ type_ start__ end____ width___ exp.time_ 14 omega -8.00 18.00 1.0000 32.0000 omega____ theta____ kappa____ phi______ frames - 38.5144 107.0000 -146.0000 26 #__ type_ start__ end____ width___ exp.time_ 15 omega -34.00 28.00 1.0000 32.0000 omega____ theta____ kappa____ phi______ frames - 38.5144 -37.0000 120.0000 62 #__ type_ start__ end____ width___ exp.time_ 16 omega 13.00 54.00 1.0000 32.0000 omega____ theta____ kappa____ phi______ frames - 38.5144 37.0000 -90.0000 41 #__ type_ start__ end____ width___ exp.time_ 17 omega -34.00 28.00 1.0000 32.0000 omega____ theta____ kappa____ phi______ frames - 38.5144 -37.0000 -60.0000 62 ; _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.008145 _diffrn_orient_matrix_UB_12 -0.0170799 _diffrn_orient_matrix_UB_13 -0.0610519 _diffrn_orient_matrix_UB_21 0.0955882 _diffrn_orient_matrix_UB_22 -0.0033358 _diffrn_orient_matrix_UB_23 0.0057654 _diffrn_orient_matrix_UB_31 -0.018886 _diffrn_orient_matrix_UB_32 -0.0609564 _diffrn_orient_matrix_UB_33 -0.0161918 _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 3624 _reflns_number_total 3804 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _refine_diff_density_max 0.894 _refine_diff_density_min -0.659 _refine_diff_density_rms 0.086 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.106 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 277 _refine_ls_number_reflns 3804 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0196 _refine_ls_R_factor_gt 0.0179 _refine_ls_restrained_S_all 1.106 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; calc w=1/[\s^2^(Fo^2^)+(0.0179P)^2^+1.4301P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0421 _refine_ls_wR_factor_ref 0.0429 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 Re1 Re 0.671529(18) 0.766459(11) 0.613690(11) 0.02061(5) Uani 1 1 d . . . Br1 Br 1.01898(5) 0.84651(3) 0.72274(3) 0.02520(8) Uani 1 1 d . . . O1 O 0.2740(4) 0.6731(2) 0.4768(3) 0.0389(6) Uani 1 1 d . . . O2 O 0.5366(5) 0.9649(3) 0.8213(3) 0.0562(8) Uani 1 1 d . . . O3 O 0.6329(4) 0.6087(3) 0.7265(3) 0.0515(8) Uani 1 1 d . . . O4 O 0.9689(5) 0.6671(2) 0.0067(2) 0.0469(7) Uani 1 1 d . . . O5 O 0.3780(5) 0.7873(3) 0.2510(4) 0.0797(12) Uani 1 1 d . . . N1 N 0.7268(3) 0.8649(2) 0.5238(2) 0.0176(5) Uani 1 1 d . . . N2 N 0.7763(4) 0.6417(2) 0.4618(2) 0.0203(6) Uani 1 1 d . . . N3 N 0.9291(4) 0.8308(3) 0.1747(3) 0.0292(7) Uani 1 1 d D . . H3 H 0.917(5) 0.9061(19) 0.202(3) 0.035 Uiso 1 1 d D . . C1 C 0.4213(5) 0.7072(3) 0.5253(3) 0.0277(8) Uani 1 1 d . . . C2 C 0.5888(5) 0.8902(3) 0.7437(3) 0.0330(8) Uani 1 1 d . . . C3 C 0.6474(5) 0.6683(3) 0.6849(3) 0.0316(8) Uani 1 1 d . . . C4 C 0.7057(4) 0.9776(3) 0.5593(3) 0.0201(7) Uani 1 1 d . . . H4 H 0.6650 1.0221 0.6315 0.024 Uiso 1 1 calc R . . C5 C 0.7410(4) 1.0326(3) 0.4946(3) 0.0223(7) Uani 1 1 d . . . H5 H 0.7257 1.1137 0.5231 0.027 Uiso 1 1 calc R . . C6 C 0.7979(4) 0.9701(3) 0.3902(3) 0.0216(7) Uani 1 1 d . . . H6 H 0.8168 1.0064 0.3440 0.026 Uiso 1 1 calc R . . C7 C 0.8284(4) 0.8522(3) 0.3513(3) 0.0185(6) Uani 1 1 d . . . C8 C 0.8953(5) 0.7785(3) 0.2439(3) 0.0234(7) Uani 1 1 d . . . C9 C 0.9219(5) 0.6654(3) 0.2150(3) 0.0262(7) Uani 1 1 d . . . H9 H 0.9667 0.6184 0.1451 0.031 Uiso 1 1 calc R . . C10 C 0.8844(4) 0.6152(3) 0.2868(3) 0.0224(7) Uani 1 1 d . . . C11 C 0.9097(5) 0.4985(3) 0.2586(3) 0.0275(8) Uani 1 1 d . . . H11 H 0.9552 0.4490 0.1898 0.033 Uiso 1 1 calc R . . C12 C 0.8683(5) 0.4571(3) 0.3313(3) 0.0299(8) Uani 1 1 d . . . H12 H 0.8848 0.3783 0.3133 0.036 Uiso 1 1 calc R . . C13 C 0.8014(5) 0.5308(3) 0.4323(3) 0.0263(7) Uani 1 1 d . . . H13 H 0.7728 0.5003 0.4817 0.032 Uiso 1 1 calc R . . C14 C 0.8178(4) 0.6834(3) 0.3894(3) 0.0173(6) Uani 1 1 d . . . C15 C 0.7903(4) 0.8023(3) 0.4213(3) 0.0164(6) Uani 1 1 d . . . C16 C 0.9629(6) 0.7731(3) 0.0615(3) 0.0357(9) Uani 1 1 d . . . C17 C 0.9889(8) 0.8519(4) 0.0096(4) 0.0592(14) Uani 1 1 d . . . H17B H 1.0432 0.8106 -0.0604 0.089 Uiso 1 1 calc R . . H17C H 1.0713 0.9260 0.0696 0.089 Uiso 1 1 calc R . . H17A H 0.8693 0.8709 -0.0145 0.089 Uiso 1 1 calc R . . C18 C 0.3780(7) 0.5812(4) 0.1532(6) 0.0738(17) Uani 1 1 d . . . H18B H 0.3487 0.5879 0.2262 0.111 Uiso 1 1 calc R . . H18C H 0.4941 0.5495 0.1418 0.111 Uiso 1 1 calc R . . H18A H 0.2788 0.5271 0.0844 0.111 Uiso 1 1 calc R . . C19 C 0.3965(6) 0.6995(4) 0.1636(5) 0.0563(13) Uani 1 1 d . . . C20 C 0.4398(8) 0.7085(6) 0.0600(6) 0.0837(19) Uani 1 1 d . . . H20C H 0.4499 0.7920 0.0791 0.126 Uiso 1 1 calc R . . H20A H 0.3411 0.6596 -0.0110 0.126 Uiso 1 1 calc R . . H20B H 0.5568 0.6798 0.0443 0.126 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 Re1 0.02782(8) 0.01773(7) 0.02013(8) 0.01182(6) 0.00777(5) 0.00197(5) Br1 0.03214(19) 0.02230(16) 0.02382(17) 0.01463(14) 0.00365(14) 0.00113(13) O1 0.0401(17) 0.0330(15) 0.0476(17) 0.0247(13) 0.0054(14) 0.0036(12) O2 0.071(2) 0.0433(17) 0.0458(18) 0.0084(15) 0.0358(17) 0.0132(16) O3 0.063(2) 0.0577(19) 0.060(2) 0.0508(18) 0.0123(16) 0.0022(15) O4 0.080(2) 0.0313(16) 0.0252(14) 0.0088(12) 0.0200(14) 0.0040(14) O5 0.063(2) 0.044(2) 0.080(3) -0.0110(19) 0.020(2) 0.0131(17) N1 0.0200(13) 0.0167(13) 0.0180(13) 0.0102(11) 0.0046(11) 0.0029(10) N2 0.0230(14) 0.0173(13) 0.0222(14) 0.0115(12) 0.0032(11) 0.0039(11) N3 0.0435(18) 0.0262(15) 0.0206(15) 0.0129(13) 0.0107(13) 0.0037(14) C1 0.036(2) 0.0176(16) 0.042(2) 0.0212(16) 0.0189(18) 0.0087(15) C2 0.040(2) 0.032(2) 0.034(2) 0.0211(18) 0.0134(17) 0.0013(17) C3 0.033(2) 0.0322(19) 0.032(2) 0.0188(17) 0.0079(16) 0.0020(16) C4 0.0217(16) 0.0173(16) 0.0211(16) 0.0088(13) 0.0059(13) 0.0056(12) C5 0.0213(16) 0.0170(16) 0.0304(18) 0.0139(14) 0.0032(14) 0.0040(13) C6 0.0238(17) 0.0232(17) 0.0239(17) 0.0166(14) 0.0046(13) 0.0031(13) C7 0.0173(15) 0.0199(16) 0.0193(16) 0.0111(14) 0.0030(13) 0.0014(12) C8 0.0253(17) 0.0243(17) 0.0213(17) 0.0111(14) 0.0084(14) 0.0029(14) C9 0.0311(19) 0.0256(18) 0.0213(17) 0.0095(15) 0.0112(14) 0.0059(14) C10 0.0227(17) 0.0189(16) 0.0214(16) 0.0075(14) 0.0031(13) 0.0026(13) C11 0.0302(19) 0.0203(17) 0.0250(18) 0.0060(15) 0.0054(15) 0.0055(14) C12 0.039(2) 0.0143(16) 0.0317(19) 0.0081(15) 0.0049(16) 0.0081(14) C13 0.0325(19) 0.0175(16) 0.0288(18) 0.0137(15) 0.0009(15) 0.0005(14) C14 0.0182(15) 0.0171(15) 0.0158(15) 0.0088(13) 0.0005(12) 0.0012(12) C15 0.0144(15) 0.0180(15) 0.0149(15) 0.0073(13) 0.0015(12) 0.0024(12) C16 0.047(2) 0.034(2) 0.0240(19) 0.0133(17) 0.0084(17) -0.0027(17) C17 0.115(4) 0.042(2) 0.025(2) 0.018(2) 0.025(2) 0.001(3) C18 0.052(3) 0.042(3) 0.094(4) 0.011(3) 0.006(3) 0.009(2) C19 0.029(2) 0.042(3) 0.064(3) 0.002(2) 0.004(2) 0.0082(19) C20 0.052(3) 0.081(4) 0.093(5) 0.026(4) 0.010(3) 0.016(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Re1 Br1 2.6197(4) . ? Re1 N1 2.174(2) . ? Re1 N2 2.172(3) . ? Re1 C1 1.917(4) . ? Re1 C2 1.913(4) . ? Re1 C3 1.920(4) . ? O1 C1 1.117(4) . ? O2 C2 1.158(5) . ? O3 C3 1.148(4) . ? O4 C16 1.210(5) . ? O5 C19 1.196(5) . ? N1 C4 1.327(4) . ? N1 C15 1.371(4) . ? N2 C13 1.327(4) . ? N2 C14 1.362(4) . ? N3 H3 0.876(19) . ? N3 C8 1.411(4) . ? N3 C16 1.375(5) . ? C4 H4 0.9500 . ? C4 C5 1.389(4) . ? C5 H5 0.9500 . ? C5 C6 1.364(5) . ? C6 H6 0.9500 . ? C6 C7 1.402(4) . ? C7 C8 1.456(4) . ? C7 C15 1.404(4) . ? C8 C9 1.359(5) . ? C9 H9 0.9500 . ? C9 C10 1.428(5) . ? C10 C11 1.403(5) . ? C10 C14 1.397(4) . ? C11 H11 0.9500 . ? C11 C12 1.363(5) . ? C12 H12 0.9500 . ? C12 C13 1.399(5) . ? C13 H13 0.9500 . ? C14 C15 1.423(4) . ? C16 C17 1.493(5) . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C17 H17A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C18 H18A 0.9800 . ? C18 C19 1.465(7) . ? C19 C20 1.500(8) . ? C20 H20C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 Re1 177.9(3) . . ? O2 C2 Re1 179.1(4) . . ? O3 C3 Re1 179.4(3) . . ? O4 C16 N3 123.5(3) . . ? O4 C16 C17 122.1(3) . . ? O5 C19 C18 122.3(6) . . ? O5 C19 C20 119.9(5) . . ? N1 Re1 Br1 83.88(7) . . ? N1 C4 H4 118.9 . . ? N1 C4 C5 122.2(3) . . ? N1 C15 C7 122.3(3) . . ? N1 C15 C14 116.4(3) . . ? N2 Re1 Br1 85.31(7) . . ? N2 Re1 N1 75.57(9) . . ? N2 C13 C12 122.6(3) . . ? N2 C13 H13 118.7 . . ? N2 C14 C10 123.1(3) . . ? N2 C14 C15 117.5(3) . . ? N3 C8 C7 116.7(3) . . ? N3 C16 C17 114.4(3) . . ? C1 Re1 Br1 176.50(10) . . ? C1 Re1 N1 93.26(12) . . ? C1 Re1 N2 92.03(13) . . ? C1 Re1 C3 90.36(15) . . ? C2 Re1 Br1 92.71(12) . . ? C2 Re1 N1 98.01(12) . . ? C2 Re1 N2 173.44(12) . . ? C2 Re1 C1 89.68(16) . . ? C2 Re1 C3 88.41(15) . . ? C3 Re1 Br1 92.26(11) . . ? C3 Re1 N1 172.64(13) . . ? C3 Re1 N2 97.92(13) . . ? C4 N1 Re1 126.2(2) . . ? C4 N1 C15 118.5(3) . . ? C4 C5 H5 120.0 . . ? C5 C4 H4 118.9 . . ? C5 C6 H6 120.1 . . ? C5 C6 C7 119.8(3) . . ? C6 C5 C4 120.0(3) . . ? C6 C5 H5 120.0 . . ? C6 C7 C8 124.7(3) . . ? C6 C7 C15 117.1(3) . . ? C7 C6 H6 120.1 . . ? C7 C15 C14 121.3(3) . . ? C8 N3 H3 118(3) . . ? C8 C9 H9 119.1 . . ? C8 C9 C10 121.8(3) . . ? C9 C8 N3 123.5(3) . . ? C9 C8 C7 119.9(3) . . ? C10 C9 H9 119.1 . . ? C10 C11 H11 120.5 . . ? C10 C14 C15 119.4(3) . . ? C11 C10 C9 122.9(3) . . ? C11 C12 H12 120.0 . . ? C11 C12 C13 119.9(3) . . ? C12 C11 C10 119.1(3) . . ? C12 C11 H11 120.5 . . ? C12 C13 H13 118.7 . . ? C13 N2 Re1 127.1(2) . . ? C13 N2 C14 117.7(3) . . ? C13 C12 H12 120.0 . . ? C14 N2 Re1 115.1(2) . . ? C14 C10 C9 119.5(3) . . ? C14 C10 C11 117.6(3) . . ? C15 N1 Re1 115.31(19) . . ? C15 C7 C8 118.2(3) . . ? C16 N3 H3 115(3) . . ? C16 N3 C8 126.6(3) . . ? C16 C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? C16 C17 H17A 109.5 . . ? H17B C17 H17C 109.5 . . ? H17B C17 H17A 109.5 . . ? H17C C17 H17A 109.5 . . ? C18 C19 C20 117.9(5) . . ? H18B C18 H18C 109.5 . . ? H18B C18 H18A 109.5 . . ? H18C C18 H18A 109.5 . . ? C19 C18 H18B 109.5 . . ? C19 C18 H18C 109.5 . . ? C19 C18 H18A 109.5 . . ? C19 C20 H20C 109.5 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20C C20 H20A 109.5 . . ? H20C C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? # Attachment '- Bu4N_phenNCOCF3.cif' data_[Bu4N][phenNCOCF3] _database_code_depnum_ccdc_archive 'CCDC 823829' #TrackingRef '- Bu4N_phenNCOCF3.cif' _audit_creation_date 2011-01-21 _audit_creation_method ; Olex2 1.1 (compiled 2010.09.30 svn.r1450, GUI svn.r3284) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C16 H36 N, C14 H7 F3 N3 O, H2 O' _chemical_formula_sum 'C30 H45 F3 N4 O2' _chemical_formula_weight 550.70 _chemical_melting_point ? 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' F F 0.0727 0.0534 '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' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 8.2395(3) _cell_length_b 18.8039(8) _cell_length_c 21.5491(8) _cell_angle_alpha 69.356(4) _cell_angle_beta 89.001(3) _cell_angle_gamma 87.549(4) _cell_volume 3121.5(2) _cell_formula_units_Z 4 _cell_measurement_reflns_used 24588 _cell_measurement_temperature 133(2) _cell_measurement_theta_max 73.2931 _cell_measurement_theta_min 3.8707 _exptl_absorpt_coefficient_mu 0.707 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_correction_T_min 0.74724 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour yellow _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.172 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'rect. Prism' _exptl_crystal_F_000 1184 _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.14 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0326 _diffrn_reflns_av_unetI/netI 0.0233 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 40552 _diffrn_reflns_theta_full 67.00 _diffrn_reflns_theta_max 67.00 _diffrn_reflns_theta_min 3.87 _diffrn_ambient_temperature 133.0 _diffrn_detector_area_resol_mean 16.127 _diffrn_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.989 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -70.00 30.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 -77.0000 90.0000 100 #__ type_ start__ end____ width___ exp.time_ 2 omega -12.00 66.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 37.0000 -120.0000 78 #__ type_ start__ end____ width___ exp.time_ 3 omega -71.00 -4.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 -37.0000 150.0000 67 #__ type_ start__ end____ width___ exp.time_ 4 omega 1.00 26.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 -37.0000 150.0000 25 #__ type_ start__ end____ width___ exp.time_ 5 omega -24.00 2.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - 18.0000 99.0000 -115.0000 26 #__ type_ start__ end____ width___ exp.time_ 6 omega -11.00 14.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - 26.0000 90.0000 79.0000 25 #__ type_ start__ end____ width___ exp.time_ 7 omega -35.00 -9.00 1.0000 24.0000 omega____ theta____ kappa____ phi______ frames - -42.0000 -88.0000 -107.0000 26 #__ type_ start__ end____ width___ exp.time_ 8 omega -44.00 -10.00 1.0000 24.0000 omega____ theta____ kappa____ phi______ frames - -44.0000 -84.0000 15.0000 34 #__ type_ start__ end____ width___ exp.time_ 9 omega -41.00 -15.00 1.0000 24.0000 omega____ theta____ kappa____ phi______ frames - -44.0000 -82.0000 134.0000 26 #__ type_ start__ end____ width___ exp.time_ 10 omega -35.00 -9.00 1.0000 24.0000 omega____ theta____ kappa____ phi______ frames - -44.0000 -86.0000 102.0000 26 #__ type_ start__ end____ width___ exp.time_ 11 omega 15.00 41.00 1.0000 24.0000 omega____ theta____ kappa____ phi______ frames - 44.0000 77.0000 42.0000 26 #__ type_ start__ end____ width___ exp.time_ 12 omega 47.00 114.00 1.0000 24.0000 omega____ theta____ kappa____ phi______ frames - 44.0000 77.0000 42.0000 67 #__ type_ start__ end____ width___ exp.time_ 13 omega -38.00 -12.00 1.0000 24.0000 omega____ theta____ kappa____ phi______ frames - -46.0000 -84.0000 -49.0000 26 #__ type_ start__ end____ width___ exp.time_ 14 omega -39.00 -12.00 1.0000 24.0000 omega____ theta____ kappa____ phi______ frames - -46.0000 -84.0000 -176.0000 27 #__ type_ start__ end____ width___ exp.time_ 15 omega -43.00 -15.00 1.0000 24.0000 omega____ theta____ kappa____ phi______ frames - -48.0000 -82.0000 -160.0000 28 #__ type_ start__ end____ width___ exp.time_ 16 omega -45.00 -19.00 1.0000 24.0000 omega____ theta____ kappa____ phi______ frames - -52.0000 -83.0000 83.0000 26 #__ type_ start__ end____ width___ exp.time_ 17 omega -44.00 -18.00 1.0000 24.0000 omega____ theta____ kappa____ phi______ frames - -52.0000 -84.0000 65.0000 26 #__ type_ start__ end____ width___ exp.time_ 18 omega -46.00 -20.00 1.0000 24.0000 omega____ theta____ kappa____ phi______ frames - -52.0000 -81.0000 36.0000 26 #__ type_ start__ end____ width___ exp.time_ 19 omega -47.00 -21.00 1.0000 24.0000 omega____ theta____ kappa____ phi______ frames - -54.0000 -82.0000 111.0000 26 #__ type_ start__ end____ width___ exp.time_ 20 omega -46.00 -21.00 1.0000 24.0000 omega____ theta____ kappa____ phi______ frames - -54.0000 -84.0000 28.0000 25 #__ type_ start__ end____ width___ exp.time_ 21 omega -80.00 14.00 1.0000 24.0000 omega____ theta____ kappa____ phi______ frames - -55.0000 77.0000 -120.0000 94 #__ type_ start__ end____ width___ exp.time_ 22 omega 73.00 124.00 1.0000 24.0000 omega____ theta____ kappa____ phi______ frames - 55.0000 125.0000 120.0000 51 #__ type_ start__ end____ width___ exp.time_ 23 omega -122.00 -83.00 1.0000 24.0000 omega____ theta____ kappa____ phi______ frames - -56.0000 -77.0000 132.0000 39 #__ type_ start__ end____ width___ exp.time_ 24 omega -62.00 -27.00 1.0000 24.0000 omega____ theta____ kappa____ phi______ frames - -56.0000 -77.0000 132.0000 35 #__ type_ start__ end____ width___ exp.time_ 25 omega -65.00 -32.00 1.0000 48.0000 omega____ theta____ kappa____ phi______ frames - -60.0000 -73.0000 -30.0000 33 #__ type_ start__ end____ width___ exp.time_ 26 omega -111.00 -85.00 1.0000 48.0000 omega____ theta____ kappa____ phi______ frames - -60.0000 -73.0000 -30.0000 26 #__ type_ start__ end____ width___ exp.time_ 27 omega -58.00 -32.00 1.0000 48.0000 omega____ theta____ kappa____ phi______ frames - -62.0000 -79.0000 -72.0000 26 #__ type_ start__ end____ width___ exp.time_ 28 omega -61.00 -33.00 1.0000 48.0000 omega____ theta____ kappa____ phi______ frames - -64.0000 -79.0000 -102.0000 28 #__ type_ start__ end____ width___ exp.time_ 29 omega -86.00 -50.00 1.0000 48.0000 omega____ theta____ kappa____ phi______ frames - -64.0000 -57.0000 111.0000 36 #__ type_ start__ end____ width___ exp.time_ 30 omega -134.00 -80.00 1.0000 48.0000 omega____ theta____ kappa____ phi______ frames - -64.0000 -79.0000 -102.0000 54 #__ type_ start__ end____ width___ exp.time_ 31 omega -71.00 -34.00 1.0000 48.0000 omega____ theta____ kappa____ phi______ frames - -64.0000 -77.0000 158.0000 37 #__ type_ start__ end____ width___ exp.time_ 32 omega -68.00 -37.00 1.0000 48.0000 omega____ theta____ kappa____ phi______ frames - -64.0000 -73.0000 55.0000 31 #__ type_ start__ end____ width___ exp.time_ 33 omega -130.00 -92.00 1.0000 48.0000 omega____ theta____ kappa____ phi______ frames - -64.0000 -73.0000 55.0000 38 #__ type_ start__ end____ width___ exp.time_ 34 omega -80.00 -33.00 1.0000 48.0000 omega____ theta____ kappa____ phi______ frames - -64.0000 -79.0000 0.0000 47 #__ type_ start__ end____ width___ exp.time_ 35 omega -62.00 -33.00 1.0000 48.0000 omega____ theta____ kappa____ phi______ frames - -64.0000 -79.0000 80.0000 29 #__ type_ start__ end____ width___ exp.time_ 36 omega -71.00 -33.00 1.0000 48.0000 omega____ theta____ kappa____ phi______ frames - -64.0000 -79.0000 -127.0000 38 #__ type_ start__ end____ width___ exp.time_ 37 omega -133.00 -34.00 1.0000 48.0000 omega____ theta____ kappa____ phi______ frames - -64.0000 -77.0000 -54.0000 99 #__ type_ start__ end____ width___ exp.time_ 38 omega -111.00 -85.00 1.0000 48.0000 omega____ theta____ kappa____ phi______ frames - -64.0000 -77.0000 158.0000 26 #__ type_ start__ end____ width___ exp.time_ 39 omega -139.00 -53.00 1.0000 48.0000 omega____ theta____ kappa____ phi______ frames - -64.0000 179.0000 -150.0000 86 #__ type_ start__ end____ width___ exp.time_ 40 omega -123.00 -36.00 1.0000 48.0000 omega____ theta____ kappa____ phi______ frames - -64.0000 -73.0000 -162.0000 87 #__ type_ start__ end____ width___ exp.time_ 41 omega -93.00 5.00 1.0000 48.0000 omega____ theta____ kappa____ phi______ frames - -64.0000 77.0000 120.0000 98 #__ type_ start__ end____ width___ exp.time_ 42 omega -58.00 -33.00 1.0000 48.0000 omega____ theta____ kappa____ phi______ frames - -64.0000 -79.0000 17.0000 25 #__ type_ start__ end____ width___ exp.time_ 43 omega -134.00 -84.00 1.0000 48.0000 omega____ theta____ kappa____ phi______ frames - -64.0000 -79.0000 17.0000 50 #__ type_ start__ end____ width___ exp.time_ 44 omega 80.00 177.00 1.0000 48.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 77.0000 -60.0000 97 #__ type_ start__ end____ width___ exp.time_ 45 omega 80.00 170.00 1.0000 48.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 77.0000 30.0000 90 #__ type_ start__ end____ width___ exp.time_ 46 omega 80.00 177.00 1.0000 48.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 77.0000 -30.0000 97 #__ type_ start__ end____ width___ exp.time_ 47 omega 80.00 105.00 1.0000 48.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 77.0000 -180.0000 25 #__ type_ start__ end____ width___ exp.time_ 48 omega 80.00 156.00 1.0000 48.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 77.0000 -90.0000 76 #__ type_ start__ end____ width___ exp.time_ 49 omega 80.00 157.00 1.0000 48.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 77.0000 120.0000 77 #__ type_ start__ end____ width___ exp.time_ 50 omega 80.00 166.00 1.0000 48.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 77.0000 60.0000 86 #__ type_ start__ end____ width___ exp.time_ 51 omega 80.00 164.00 1.0000 48.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 77.0000 -150.0000 84 #__ type_ start__ end____ width___ exp.time_ 52 omega 120.00 178.00 1.0000 48.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 77.0000 0.0000 58 #__ type_ start__ end____ width___ exp.time_ 53 omega 80.00 105.00 1.0000 48.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 77.0000 0.0000 25 #__ type_ start__ end____ width___ exp.time_ 54 omega 117.00 178.00 1.0000 48.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 77.0000 -180.0000 61 #__ type_ start__ end____ width___ exp.time_ 55 omega 118.00 178.00 1.0000 48.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 77.0000 90.0000 60 #__ type_ start__ end____ width___ exp.time_ 56 omega 80.00 105.00 1.0000 48.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 77.0000 90.0000 25 #__ type_ start__ end____ width___ exp.time_ 57 omega 80.00 174.00 1.0000 48.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 77.0000 150.0000 94 #__ type_ start__ end____ width___ exp.time_ 58 omega 80.00 174.00 1.0000 48.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 77.0000 -120.0000 94 #__ type_ start__ end____ width___ exp.time_ 59 omega 90.00 115.00 1.0000 48.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 50.0000 -150.0000 25 #__ type_ start__ end____ width___ exp.time_ 60 omega 80.00 146.00 1.0000 48.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -88.0000 -81.0000 66 #__ type_ start__ end____ width___ exp.time_ 61 omega 47.00 73.00 1.0000 48.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -88.0000 -81.0000 26 #__ type_ start__ end____ width___ exp.time_ 62 omega 84.00 146.00 1.0000 48.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -88.0000 -179.0000 62 #__ type_ start__ end____ width___ exp.time_ 63 omega 51.00 77.00 1.0000 48.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -88.0000 -179.0000 26 #__ type_ start__ end____ width___ exp.time_ 64 omega 95.00 122.00 1.0000 48.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 50.0000 120.0000 27 #__ type_ start__ end____ width___ exp.time_ 65 omega 53.00 146.00 1.0000 48.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -88.0000 108.0000 93 #__ type_ start__ end____ width___ exp.time_ 66 omega 76.00 105.00 1.0000 48.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 25.0000 60.0000 29 #__ type_ start__ end____ width___ exp.time_ 67 omega 82.00 102.00 1.0000 48.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -88.0000 0.0000 20 ; _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0036354 _diffrn_orient_matrix_UB_12 0.0503067 _diffrn_orient_matrix_UB_13 -0.0739564 _diffrn_orient_matrix_UB_21 -0.0578195 _diffrn_orient_matrix_UB_22 -0.066733 _diffrn_orient_matrix_UB_23 -0.018563 _diffrn_orient_matrix_UB_31 -0.1779513 _diffrn_orient_matrix_UB_32 0.0263168 _diffrn_orient_matrix_UB_33 0.0047237 _diffrn_radiation_monochromator mirror _diffrn_radiation_source 'Enhance Ultra (Cu) X-ray Source' _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.5418 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 9079 _reflns_number_total 11014 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _refine_diff_density_max 0.343 _refine_diff_density_min -0.379 _refine_diff_density_rms 0.050 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.104 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 760 _refine_ls_number_reflns 11014 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0610 _refine_ls_R_factor_gt 0.0498 _refine_ls_restrained_S_all 1.104 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ;calc w=1/[\s^2^(Fo^2^)+(0.0597P) ^2^+2.0154P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1377 _refine_ls_wR_factor_ref 0.1467 _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. ; # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.500 0.000 0.500 208 45 ' ' _platon_squeeze_details ; ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F1 F 0.37191(18) 0.46062(8) 0.00109(8) 0.0684(5) Uani 1 1 d . . . F2 F 0.1621(2) 0.47759(7) 0.05365(7) 0.0580(4) Uani 1 1 d . . . F3 F 0.1456(2) 0.42228(8) -0.01565(8) 0.0678(5) Uani 1 1 d . . . F4 F 0.74523(16) 0.73153(8) 0.45074(7) 0.0534(4) Uani 1 1 d . . . F5 F 0.49470(16) 0.72640(7) 0.47964(6) 0.0470(3) Uani 1 1 d . . . F6 F 0.5898(2) 0.83205(7) 0.41757(7) 0.0599(4) Uani 1 1 d . . . O1 O 0.28475(19) 0.35560(8) 0.14397(7) 0.0403(4) Uani 1 1 d . . . O2 O 0.4063(2) 0.33215(10) 0.27190(9) 0.0484(4) Uani 1 1 d D . . H2A H 0.381(4) 0.3418(15) 0.2317(7) 0.073 Uiso 1 1 d D . . H2B H 0.399(4) 0.3740(10) 0.2790(13) 0.073 Uiso 1 1 d D . . O3 O 0.5950(2) 0.79103(9) 0.31285(8) 0.0514(4) Uani 1 1 d . . . O4 O 0.60421(19) 0.86868(9) 0.17053(7) 0.0387(3) Uani 1 1 d D . . H4A H 0.599(3) 0.8475(13) 0.2123(5) 0.058 Uiso 1 1 d D . . H4B H 0.557(3) 0.9121(8) 0.1610(12) 0.058 Uiso 1 1 d D . . N1 N 0.3870(2) 0.03351(10) 0.08478(9) 0.0375(4) Uani 1 1 d . . . N2 N 0.4702(2) -0.00801(9) 0.21574(9) 0.0354(4) Uani 1 1 d . . . N3 N 0.3064(2) 0.29667(9) 0.06430(8) 0.0310(4) Uani 1 1 d . . . N4 N 0.89977(19) 0.36914(9) 0.24681(8) 0.0298(4) Uani 1 1 d . . . N5 N 0.3713(2) 0.44588(10) 0.33677(9) 0.0388(4) Uani 1 1 d . . . N6 N 0.4504(2) 0.51120(10) 0.20556(9) 0.0382(4) Uani 1 1 d . . . N7 N 0.5029(2) 0.67177(10) 0.38026(8) 0.0362(4) Uani 1 1 d . . . N8 N 0.0659(2) 0.85016(10) 0.24507(8) 0.0350(4) Uani 1 1 d . . . C1 C 0.3460(3) 0.05478(13) 0.02158(11) 0.0407(5) Uani 1 1 d . . . H1 H 0.3448 0.0166 0.0021 0.049 Uiso 1 1 calc R . . C2 C 0.3044(3) 0.12935(12) -0.01850(11) 0.0385(5) Uani 1 1 d . . . H2 H 0.2762 0.1413 -0.0637 0.046 Uiso 1 1 calc R . . C3 C 0.3051(3) 0.18493(12) 0.00898(10) 0.0340(4) Uani 1 1 d . . . H3 H 0.2766 0.2362 -0.0171 0.041 Uiso 1 1 calc R . . C4 C 0.3483(2) 0.16579(11) 0.07582(10) 0.0290(4) Uani 1 1 d . . . C5 C 0.3491(2) 0.22345(11) 0.10675(10) 0.0284(4) Uani 1 1 d . . . C6 C 0.3929(2) 0.20084(11) 0.17196(10) 0.0309(4) Uani 1 1 d . . . H6 H 0.3944 0.2377 0.1928 0.037 Uiso 1 1 calc R . . C7 C 0.4366(2) 0.12331(11) 0.20976(10) 0.0306(4) Uani 1 1 d . . . C8 C 0.4825(3) 0.10049(12) 0.27677(10) 0.0375(5) Uani 1 1 d . . . H8 H 0.4858 0.1368 0.2981 0.045 Uiso 1 1 calc R . . C9 C 0.5223(3) 0.02523(12) 0.31108(11) 0.0398(5) Uani 1 1 d . . . H9 H 0.5553 0.0089 0.3561 0.048 Uiso 1 1 calc R . . C10 C 0.5134(3) -0.02682(12) 0.27856(11) 0.0391(5) Uani 1 1 d . . . H10 H 0.5399 -0.0788 0.3029 0.047 Uiso 1 1 calc R . . C11 C 0.4329(2) 0.06656(11) 0.18116(10) 0.0300(4) Uani 1 1 d . . . C12 C 0.3891(2) 0.08867(11) 0.11211(10) 0.0294(4) Uani 1 1 d . . . C13 C 0.2810(2) 0.35194(11) 0.08714(10) 0.0290(4) Uani 1 1 d . . . C14 C 0.2391(2) 0.42774(11) 0.03141(10) 0.0314(4) Uani 1 1 d . . . C15 C 1.0122(2) 0.29855(11) 0.26873(10) 0.0312(4) Uani 1 1 d . . . H15A H 1.0745 0.2968 0.2296 0.037 Uiso 1 1 calc R . . H15B H 1.0910 0.3040 0.3008 0.037 Uiso 1 1 calc R . . C16 C 0.9315(3) 0.22311(12) 0.30034(11) 0.0378(5) Uani 1 1 d . . . H16A H 0.8583 0.2145 0.2679 0.045 Uiso 1 1 calc R . . H16B H 0.8654 0.2241 0.3389 0.045 Uiso 1 1 calc R . . C17 C 1.0603(3) 0.15902(13) 0.32280(12) 0.0478(6) Uani 1 1 d . . . H17A H 1.1290 0.1603 0.2843 0.057 Uiso 1 1 calc R . . H17B H 1.1307 0.1675 0.3561 0.057 Uiso 1 1 calc R . . C18 C 0.9896(4) 0.08090(14) 0.35271(14) 0.0601(7) Uani 1 1 d . . . H18A H 0.9203 0.0718 0.3200 0.090 Uiso 1 1 calc R . . H18B H 0.9248 0.0784 0.3919 0.090 Uiso 1 1 calc R . . H18C H 1.0780 0.0420 0.3655 0.090 Uiso 1 1 calc R . . C19 C 0.8015(2) 0.37577(13) 0.30505(10) 0.0349(5) Uani 1 1 d . . . H19B H 0.7354 0.4240 0.2894 0.042 Uiso 1 1 calc R . . H19A H 0.7255 0.3336 0.3197 0.042 Uiso 1 1 calc R . . C20 C 0.8992(3) 0.37408(15) 0.36443(11) 0.0429(5) Uani 1 1 d . . . H20B H 0.9687 0.4187 0.3518 0.051 Uiso 1 1 calc R . . H20A H 0.9707 0.3275 0.3794 0.051 Uiso 1 1 calc R . . C21 C 0.7861(3) 0.37527(15) 0.42068(11) 0.0453(6) Uani 1 1 d . . . H21B H 0.7162 0.4223 0.4055 0.054 Uiso 1 1 calc R . . H21A H 0.7147 0.3314 0.4321 0.054 Uiso 1 1 calc R . . C22 C 0.8775(3) 0.37188(16) 0.48232(12) 0.0530(6) Uani 1 1 d . . . H22C H 0.9372 0.4185 0.4729 0.080 Uiso 1 1 calc R . . H22A H 0.9541 0.3278 0.4953 0.080 Uiso 1 1 calc R . . H22B H 0.8001 0.3671 0.5185 0.080 Uiso 1 1 calc R . . C23 C 1.0082(2) 0.43631(11) 0.21731(10) 0.0304(4) Uani 1 1 d . . . H23B H 1.0823 0.4377 0.2525 0.037 Uiso 1 1 calc R . . H23A H 1.0761 0.4271 0.1823 0.037 Uiso 1 1 calc R . . C24 C 0.9234(3) 0.51401(12) 0.18759(11) 0.0356(5) Uani 1 1 d . . . H24B H 0.8557 0.5250 0.2218 0.043 Uiso 1 1 calc R . . H24A H 0.8516 0.5148 0.1510 0.043 Uiso 1 1 calc R . . C25 C 1.0503(3) 0.57427(12) 0.16139(12) 0.0390(5) Uani 1 1 d . . . H25B H 1.1184 0.5742 0.1988 0.047 Uiso 1 1 calc R . . H25A H 1.1219 0.5606 0.1296 0.047 Uiso 1 1 calc R . . C26 C 0.9774(3) 0.65419(13) 0.12714(13) 0.0480(6) Uani 1 1 d . . . H26A H 0.9128 0.6553 0.0890 0.072 Uiso 1 1 calc R . . H26C H 1.0648 0.6901 0.1120 0.072 Uiso 1 1 calc R . . H26B H 0.9075 0.6686 0.1584 0.072 Uiso 1 1 calc R . . C27 C 0.7775(2) 0.36474(12) 0.19643(10) 0.0322(4) Uani 1 1 d . . . H27A H 0.7107 0.3200 0.2178 0.039 Uiso 1 1 calc R . . H27B H 0.7039 0.4105 0.1847 0.039 Uiso 1 1 calc R . . C28 C 0.8485(3) 0.35888(12) 0.13281(10) 0.0340(5) Uani 1 1 d . . . H28A H 0.9348 0.3181 0.1436 0.041 Uiso 1 1 calc R . . H28B H 0.8977 0.4074 0.1063 0.041 Uiso 1 1 calc R . . C29 C 0.7155(3) 0.34122(13) 0.09280(11) 0.0391(5) Uani 1 1 d . . . H29A H 0.6626 0.2943 0.1208 0.047 Uiso 1 1 calc R . . H29B H 0.6322 0.3833 0.0808 0.047 Uiso 1 1 calc R . . C30 C 0.7791(3) 0.33056(13) 0.03016(11) 0.0458(6) Uani 1 1 d . . . H30C H 0.8175 0.3790 -0.0006 0.069 Uiso 1 1 calc R . . H30A H 0.6917 0.3133 0.0092 0.069 Uiso 1 1 calc R . . H30B H 0.8691 0.2925 0.0413 0.069 Uiso 1 1 calc R . . C31 C 0.3358(3) 0.41413(13) 0.40061(11) 0.0412(5) Uani 1 1 d . . . H31 H 0.3007 0.3633 0.4161 0.049 Uiso 1 1 calc R . . C32 C 0.3468(3) 0.45084(13) 0.44634(11) 0.0405(5) Uani 1 1 d . . . H32 H 0.3205 0.4255 0.4917 0.049 Uiso 1 1 calc R . . C33 C 0.3966(3) 0.52430(12) 0.42444(10) 0.0365(5) Uani 1 1 d . . . H33 H 0.4057 0.5503 0.4548 0.044 Uiso 1 1 calc R . . C34 C 0.4340(2) 0.56114(12) 0.35697(10) 0.0329(4) Uani 1 1 d . . . C35 C 0.4856(2) 0.63931(12) 0.33160(10) 0.0339(4) Uani 1 1 d . . . C36 C 0.5135(3) 0.67179(12) 0.26474(10) 0.0370(5) Uani 1 1 d . . . H36 H 0.5418 0.7236 0.2470 0.044 Uiso 1 1 calc R . . C37 C 0.5013(2) 0.63021(12) 0.22098(10) 0.0349(5) Uani 1 1 d . . . C38 C 0.5345(3) 0.66330(13) 0.15235(10) 0.0397(5) Uani 1 1 d . . . H38 H 0.5637 0.7149 0.1339 0.048 Uiso 1 1 calc R . . C39 C 0.5243(3) 0.62085(14) 0.11286(11) 0.0418(5) Uani 1 1 d . . . H39 H 0.5454 0.6425 0.0666 0.050 Uiso 1 1 calc R . . C40 C 0.4823(3) 0.54490(14) 0.14160(11) 0.0408(5) Uani 1 1 d . . . H40 H 0.4763 0.5157 0.1136 0.049 Uiso 1 1 calc R . . C41 C 0.4586(2) 0.55376(12) 0.24472(10) 0.0340(5) Uani 1 1 d . . . C42 C 0.4202(2) 0.51888(12) 0.31478(10) 0.0334(4) Uani 1 1 d . . . C43 C 0.5575(2) 0.73983(11) 0.36597(10) 0.0339(5) Uani 1 1 d . . . C44 C 0.5934(3) 0.75740(12) 0.42827(11) 0.0383(5) Uani 1 1 d . . . C45 C 0.1914(2) 0.85284(12) 0.19165(10) 0.0335(4) Uani 1 1 d . A . H45B H 0.2608 0.8965 0.1854 0.040 Uiso 1 1 calc R . . H45A H 0.2619 0.8060 0.2078 0.040 Uiso 1 1 calc R . . C46 C 0.1225(3) 0.85980(12) 0.12465(11) 0.0376(5) Uani 1 1 d . . . H46A H 0.0383 0.8218 0.1309 0.045 Uiso 1 1 calc R A . H46B H 0.0709 0.9111 0.1034 0.045 Uiso 1 1 calc R . . C47 C 0.2567(3) 0.84687(13) 0.08001(11) 0.0406(5) Uani 1 1 d . A . H47B H 0.3464 0.8809 0.0784 0.049 Uiso 1 1 calc R . . H47A H 0.3002 0.7938 0.0994 0.049 Uiso 1 1 calc R . . C48 C 0.1995(3) 0.86133(15) 0.01010(12) 0.0493(6) Uani 1 1 d . . . H48B H 0.2902 0.8518 -0.0163 0.074 Uiso 1 1 calc R A . H48C H 0.1595 0.9143 -0.0099 0.074 Uiso 1 1 calc R . . H48A H 0.1118 0.8273 0.0113 0.074 Uiso 1 1 calc R . . C49 C -0.0557(3) 0.91726(13) 0.22071(10) 0.0373(5) Uani 1 1 d . A . H49A H -0.1165 0.9128 0.1831 0.045 Uiso 1 1 calc R . . H49B H -0.1348 0.9134 0.2568 0.045 Uiso 1 1 calc R . . C50 C 0.0147(3) 0.99522(13) 0.19864(11) 0.0383(5) Uani 1 1 d . . . H50A H 0.0893 1.0016 0.1607 0.046 Uiso 1 1 calc R A . H50B H 0.0774 1.0008 0.2353 0.046 Uiso 1 1 calc R . . C51 C -0.1235(3) 1.05579(13) 0.17824(11) 0.0426(5) Uani 1 1 d . A . H51A H -0.1889 1.0478 0.1433 0.051 Uiso 1 1 calc R . . H51B H -0.1953 1.0497 0.2170 0.051 Uiso 1 1 calc R . . C52 C -0.0629(3) 1.13615(14) 0.15257(13) 0.0513(6) Uani 1 1 d . . . H52A H 0.0003 1.1440 0.1119 0.077 Uiso 1 1 calc R A . H52B H 0.0059 1.1437 0.1862 0.077 Uiso 1 1 calc R . . H52C H -0.1558 1.1727 0.1430 0.077 Uiso 1 1 calc R . . C53 C 0.1587(3) 0.85185(13) 0.30465(10) 0.0395(5) Uani 1 1 d . A . H53B H 0.2259 0.8973 0.2903 0.047 Uiso 1 1 calc R . . H53A H 0.2336 0.8065 0.3198 0.047 Uiso 1 1 calc R . . C54 C 0.0546(3) 0.85339(15) 0.36329(11) 0.0471(6) Uani 1 1 d . . . H54B H -0.0159 0.9003 0.3498 0.056 Uiso 1 1 calc R A . H54A H -0.0161 0.8092 0.3774 0.056 Uiso 1 1 calc R . . C55 C 0.1609(3) 0.85098(17) 0.42059(12) 0.0552(7) Uani 1 1 d . A . H55B H 0.2354 0.8937 0.4054 0.066 Uiso 1 1 calc R . . H55A H 0.2278 0.8030 0.4350 0.066 Uiso 1 1 calc R . . C56 C 0.0618(4) 0.85615(19) 0.47962(14) 0.0714(9) Uani 1 1 d . . . H56C H 0.0013 0.9052 0.4665 0.107 Uiso 1 1 calc R A . H56B H 0.1352 0.8518 0.5162 0.107 Uiso 1 1 calc R . . H56A H -0.0145 0.8148 0.4940 0.107 Uiso 1 1 calc R . . C57 C -0.0398(19) 0.7871(7) 0.2640(8) 0.037(3) Uani 0.55 1 d P A 1 H57A H -0.0953 0.7865 0.2238 0.044 Uiso 0.55 1 calc PR A 1 H57B H -0.1244 0.7954 0.2942 0.044 Uiso 0.55 1 calc PR A 1 C57A C -0.0244(18) 0.7692(7) 0.2625(8) 0.026(3) Uani 0.45 1 d PU A 2 H57D H -0.0962 0.7627 0.3013 0.031 Uiso 0.45 1 calc PR A 2 H57C H -0.0948 0.7731 0.2246 0.031 Uiso 0.45 1 calc PR A 2 C58 C 0.0446(6) 0.7089(3) 0.2983(3) 0.0316(11) Uani 0.55 1 d P A 1 H58A H 0.1238 0.6977 0.2675 0.038 Uiso 0.55 1 calc PR A 1 H58B H 0.1042 0.7089 0.3378 0.038 Uiso 0.55 1 calc PR A 1 C58A C 0.0845(9) 0.6970(4) 0.2776(4) 0.0404(16) Uani 0.45 1 d P A 2 H58C H 0.1425 0.6973 0.2369 0.048 Uiso 0.45 1 calc PR A 2 H58D H 0.1664 0.6950 0.3114 0.048 Uiso 0.45 1 calc PR A 2 C59 C -0.0829(5) 0.6477(2) 0.3192(2) 0.0348(10) Uani 0.55 1 d P A 1 H59B H -0.1641 0.6609 0.3482 0.042 Uiso 0.55 1 calc PR A 1 H59A H -0.1402 0.6478 0.2792 0.042 Uiso 0.55 1 calc PR A 1 C59A C -0.0209(7) 0.6276(3) 0.3034(3) 0.0372(12) Uani 0.45 1 d P A 2 H59D H -0.1164 0.6363 0.2740 0.045 Uiso 0.45 1 calc PR A 2 H59C H 0.0423 0.5829 0.3005 0.045 Uiso 0.45 1 calc PR A 2 C60 C -0.0123(5) 0.5686(2) 0.3555(2) 0.0444(10) Uani 0.55 1 d P A 1 H60A H 0.0649 0.5541 0.3265 0.067 Uiso 0.55 1 calc PR A 1 H60B H -0.1000 0.5325 0.3681 0.067 Uiso 0.55 1 calc PR A 1 H60C H 0.0439 0.5678 0.3955 0.067 Uiso 0.55 1 calc PR A 1 C60A C -0.0802(7) 0.6091(3) 0.3739(3) 0.0464(12) Uani 0.45 1 d P A 2 H60E H 0.0127 0.5943 0.4042 0.070 Uiso 0.45 1 calc PR A 2 H60D H -0.1547 0.5671 0.3851 0.070 Uiso 0.45 1 calc PR A 2 H60F H -0.1371 0.6540 0.3782 0.070 Uiso 0.45 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.0495(9) 0.0514(9) 0.0741(10) 0.0144(7) 0.0174(8) -0.0008(7) F2 0.0873(11) 0.0335(7) 0.0495(8) -0.0127(6) 0.0059(7) 0.0189(7) F3 0.0929(12) 0.0400(8) 0.0680(10) -0.0151(7) -0.0480(9) 0.0104(8) F4 0.0403(8) 0.0646(9) 0.0528(8) -0.0170(7) -0.0040(6) -0.0038(7) F5 0.0487(8) 0.0502(8) 0.0392(7) -0.0122(6) 0.0126(6) -0.0073(6) F6 0.0983(12) 0.0331(7) 0.0471(8) -0.0127(6) 0.0058(8) -0.0052(7) O1 0.0529(10) 0.0366(8) 0.0323(8) -0.0148(6) -0.0019(7) 0.0117(7) O2 0.0417(9) 0.0563(10) 0.0523(10) -0.0250(8) -0.0061(8) -0.0033(8) O3 0.0791(13) 0.0328(8) 0.0374(8) -0.0071(7) 0.0133(8) -0.0025(8) O4 0.0391(9) 0.0425(8) 0.0371(8) -0.0176(7) -0.0033(7) 0.0020(7) N1 0.0389(10) 0.0315(9) 0.0461(10) -0.0187(8) 0.0027(8) -0.0022(8) N2 0.0331(9) 0.0258(8) 0.0439(10) -0.0082(7) -0.0007(8) -0.0002(7) N3 0.0348(9) 0.0259(8) 0.0323(9) -0.0102(7) -0.0007(7) -0.0002(7) N4 0.0237(8) 0.0346(9) 0.0320(9) -0.0128(7) -0.0006(7) 0.0004(7) N5 0.0367(10) 0.0402(10) 0.0364(10) -0.0095(8) -0.0066(8) -0.0020(8) N6 0.0332(10) 0.0451(10) 0.0352(9) -0.0132(8) -0.0081(8) 0.0050(8) N7 0.0358(10) 0.0359(9) 0.0337(9) -0.0085(7) 0.0014(7) -0.0015(8) N8 0.0249(9) 0.0415(10) 0.0335(9) -0.0060(8) -0.0024(7) -0.0069(7) C1 0.0446(13) 0.0397(12) 0.0477(13) -0.0277(10) 0.0045(10) -0.0052(10) C2 0.0401(12) 0.0425(12) 0.0377(11) -0.0197(10) 0.0014(9) -0.0050(10) C3 0.0346(11) 0.0337(10) 0.0350(11) -0.0137(9) 0.0016(9) -0.0030(9) C4 0.0250(10) 0.0295(10) 0.0339(10) -0.0131(8) 0.0043(8) -0.0029(8) C5 0.0259(10) 0.0258(9) 0.0339(10) -0.0111(8) 0.0029(8) -0.0020(8) C6 0.0338(11) 0.0270(10) 0.0334(10) -0.0126(8) 0.0018(8) -0.0011(8) C7 0.0277(10) 0.0294(10) 0.0337(10) -0.0103(8) 0.0023(8) 0.0002(8) C8 0.0419(12) 0.0350(11) 0.0351(11) -0.0122(9) 0.0014(9) 0.0011(9) C9 0.0405(12) 0.0389(12) 0.0341(11) -0.0060(9) 0.0002(9) 0.0022(10) C10 0.0357(12) 0.0298(10) 0.0444(12) -0.0042(9) -0.0014(10) 0.0012(9) C11 0.0248(10) 0.0252(9) 0.0387(11) -0.0094(8) 0.0036(8) -0.0030(8) C12 0.0239(10) 0.0276(9) 0.0387(11) -0.0140(8) 0.0049(8) -0.0034(8) C13 0.0258(10) 0.0290(10) 0.0323(10) -0.0110(8) 0.0017(8) -0.0006(8) C14 0.0312(11) 0.0302(10) 0.0342(10) -0.0133(8) -0.0005(8) 0.0001(8) C15 0.0271(10) 0.0355(10) 0.0309(10) -0.0121(8) -0.0014(8) 0.0034(8) C16 0.0359(12) 0.0383(11) 0.0373(11) -0.0114(9) 0.0035(9) 0.0005(9) C17 0.0507(15) 0.0400(12) 0.0478(13) -0.0099(10) -0.0064(11) 0.0059(11) C18 0.080(2) 0.0398(13) 0.0546(15) -0.0102(12) -0.0032(14) 0.0001(13) C19 0.0274(11) 0.0432(12) 0.0364(11) -0.0174(9) 0.0051(8) 0.0005(9) C20 0.0284(11) 0.0646(15) 0.0435(12) -0.0288(11) 0.0058(9) -0.0038(10) C21 0.0404(13) 0.0595(15) 0.0408(12) -0.0242(11) 0.0055(10) -0.0006(11) C22 0.0504(15) 0.0717(17) 0.0446(13) -0.0306(13) 0.0044(11) 0.0012(13) C23 0.0253(10) 0.0349(10) 0.0332(10) -0.0145(8) -0.0006(8) -0.0003(8) C24 0.0295(11) 0.0351(11) 0.0447(12) -0.0172(9) -0.0039(9) 0.0015(9) C25 0.0310(11) 0.0372(11) 0.0514(13) -0.0189(10) 0.0002(10) -0.0023(9) C26 0.0480(14) 0.0340(12) 0.0639(16) -0.0193(11) -0.0009(12) -0.0039(10) C27 0.0257(10) 0.0355(10) 0.0355(11) -0.0128(9) -0.0044(8) 0.0012(8) C28 0.0319(11) 0.0367(11) 0.0345(11) -0.0133(9) -0.0036(9) -0.0045(9) C29 0.0361(12) 0.0388(11) 0.0424(12) -0.0139(10) -0.0115(9) -0.0003(9) C30 0.0581(15) 0.0413(12) 0.0391(12) -0.0147(10) -0.0155(11) -0.0034(11) C31 0.0412(13) 0.0397(12) 0.0382(12) -0.0072(10) -0.0042(10) -0.0064(10) C32 0.0411(13) 0.0422(12) 0.0330(11) -0.0064(9) -0.0002(9) -0.0051(10) C33 0.0331(11) 0.0403(11) 0.0340(11) -0.0108(9) -0.0033(9) 0.0010(9) C34 0.0245(10) 0.0364(11) 0.0338(10) -0.0078(9) -0.0059(8) 0.0056(8) C35 0.0270(10) 0.0361(11) 0.0343(11) -0.0078(9) -0.0029(8) 0.0052(8) C36 0.0356(12) 0.0343(11) 0.0354(11) -0.0058(9) -0.0018(9) 0.0052(9) C37 0.0270(10) 0.0396(11) 0.0327(10) -0.0071(9) -0.0059(8) 0.0108(9) C38 0.0345(12) 0.0422(12) 0.0343(11) -0.0044(9) -0.0030(9) 0.0092(9) C39 0.0356(12) 0.0530(14) 0.0300(11) -0.0074(10) -0.0061(9) 0.0109(10) C40 0.0320(12) 0.0550(14) 0.0349(11) -0.0163(10) -0.0065(9) 0.0093(10) C41 0.0241(10) 0.0417(11) 0.0331(10) -0.0100(9) -0.0082(8) 0.0086(9) C42 0.0264(10) 0.0357(11) 0.0341(10) -0.0074(9) -0.0076(8) 0.0042(8) C43 0.0301(11) 0.0315(10) 0.0349(11) -0.0062(9) 0.0042(8) 0.0067(8) C44 0.0388(12) 0.0312(11) 0.0395(12) -0.0062(9) 0.0059(10) 0.0002(9) C45 0.0242(10) 0.0356(11) 0.0374(11) -0.0086(9) 0.0003(8) -0.0029(8) C46 0.0346(12) 0.0377(11) 0.0387(11) -0.0112(9) -0.0034(9) -0.0020(9) C47 0.0383(12) 0.0403(12) 0.0431(12) -0.0148(10) 0.0012(10) -0.0016(10) C48 0.0536(15) 0.0539(14) 0.0463(13) -0.0243(12) 0.0018(11) -0.0080(12) C49 0.0260(10) 0.0486(13) 0.0340(11) -0.0105(9) -0.0015(8) -0.0002(9) C50 0.0304(11) 0.0461(12) 0.0391(11) -0.0163(10) -0.0013(9) 0.0011(9) C51 0.0368(12) 0.0500(13) 0.0388(12) -0.0136(10) 0.0001(10) 0.0052(10) C52 0.0519(15) 0.0476(14) 0.0531(14) -0.0170(12) -0.0014(12) 0.0049(11) C53 0.0287(11) 0.0502(13) 0.0353(11) -0.0093(10) -0.0057(9) -0.0050(9) C54 0.0412(13) 0.0595(15) 0.0374(12) -0.0129(11) -0.0021(10) -0.0041(11) C55 0.0533(16) 0.0683(17) 0.0409(13) -0.0146(12) -0.0052(11) -0.0078(13) C56 0.093(2) 0.080(2) 0.0440(15) -0.0240(15) 0.0032(15) -0.0161(18) C57 0.038(4) 0.022(5) 0.046(4) -0.006(3) -0.012(3) 0.004(3) C57A 0.018(4) 0.021(6) 0.035(3) -0.004(4) 0.003(3) -0.013(4) C58 0.019(3) 0.032(3) 0.043(3) -0.012(2) 0.003(2) 0.0000(19) C58A 0.035(4) 0.034(3) 0.052(4) -0.016(3) 0.006(3) 0.003(3) C59 0.016(2) 0.036(2) 0.045(3) -0.006(2) 0.0046(18) 0.0028(17) C59A 0.023(3) 0.042(3) 0.046(3) -0.015(3) 0.003(2) 0.002(2) C60 0.045(2) 0.031(2) 0.053(3) -0.009(2) -0.003(2) -0.0021(18) C60A 0.050(3) 0.047(3) 0.041(3) -0.014(3) 0.000(2) 0.005(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C14 1.325(2) . ? F2 C14 1.329(2) . ? F3 C14 1.319(2) . ? F4 C44 1.356(3) . ? F5 C44 1.334(2) . ? F6 C44 1.339(2) . ? O1 C13 1.252(2) . ? O2 H2A 0.849(10) . ? O2 H2B 0.852(10) . ? O3 C43 1.253(3) . ? O4 H4A 0.848(10) . ? O4 H4B 0.847(10) . ? N1 C1 1.323(3) . ? N1 C12 1.362(3) . ? N2 C10 1.324(3) . ? N2 C11 1.360(2) . ? N3 C5 1.392(2) . ? N3 C13 1.306(2) . ? N4 C15 1.520(2) . ? N4 C19 1.521(3) . ? N4 C23 1.519(3) . ? N4 C27 1.520(2) . ? N5 C31 1.325(3) . ? N5 C42 1.361(3) . ? N6 C40 1.325(3) . ? N6 C41 1.356(3) . ? N7 C35 1.399(3) . ? N7 C43 1.305(3) . ? N8 C45 1.523(3) . ? N8 C49 1.521(3) . ? N8 C53 1.516(3) . ? N8 C57 1.438(13) . ? N8 C57A 1.642(13) . ? C1 H1 0.9500 . ? C1 C2 1.395(3) . ? C2 H2 0.9500 . ? C2 C3 1.371(3) . ? C3 H3 0.9500 . ? C3 C4 1.404(3) . ? C4 C5 1.459(3) . ? C4 C12 1.413(3) . ? C5 C6 1.367(3) . ? C6 H6 0.9500 . ? C6 C7 1.431(3) . ? C7 C8 1.407(3) . ? C7 C11 1.409(3) . ? C8 H8 0.9500 . ? C8 C9 1.374(3) . ? C9 H9 0.9500 . ? C9 C10 1.395(3) . ? C10 H10 0.9500 . ? C11 C12 1.445(3) . ? C13 C14 1.536(3) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C15 C16 1.517(3) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C16 C17 1.520(3) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C17 C18 1.518(3) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19B 0.9900 . ? C19 H19A 0.9900 . ? C19 C20 1.514(3) . ? C20 H20B 0.9900 . ? C20 H20A 0.9900 . ? C20 C21 1.522(3) . ? C21 H21B 0.9900 . ? C21 H21A 0.9900 . ? C21 C22 1.519(3) . ? C22 H22C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C23 H23B 0.9900 . ? C23 H23A 0.9900 . ? C23 C24 1.517(3) . ? C24 H24B 0.9900 . ? C24 H24A 0.9900 . ? C24 C25 1.525(3) . ? C25 H25B 0.9900 . ? C25 H25A 0.9900 . ? C25 C26 1.523(3) . ? C26 H26A 0.9800 . ? C26 H26C 0.9800 . ? C26 H26B 0.9800 . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C27 C28 1.519(3) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C28 C29 1.523(3) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C29 C30 1.515(3) . ? C30 H30C 0.9800 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C31 H31 0.9500 . ? C31 C32 1.394(3) . ? C32 H32 0.9500 . ? C32 C33 1.371(3) . ? C33 H33 0.9500 . ? C33 C34 1.408(3) . ? C34 C35 1.456(3) . ? C34 C42 1.411(3) . ? C35 C36 1.372(3) . ? C36 H36 0.9500 . ? C36 C37 1.428(3) . ? C37 C38 1.414(3) . ? C37 C41 1.404(3) . ? C38 H38 0.9500 . ? C38 C39 1.362(3) . ? C39 H39 0.9500 . ? C39 C40 1.398(3) . ? C40 H40 0.9500 . ? C41 C42 1.454(3) . ? C43 C44 1.528(3) . ? C45 H45B 0.9900 . ? C45 H45A 0.9900 . ? C45 C46 1.521(3) . ? C46 H46A 0.9900 . ? C46 H46B 0.9900 . ? C46 C47 1.521(3) . ? C47 H47B 0.9900 . ? C47 H47A 0.9900 . ? C47 C48 1.514(3) . ? C48 H48B 0.9800 . ? C48 H48C 0.9800 . ? C48 H48A 0.9800 . ? C49 H49A 0.9900 . ? C49 H49B 0.9900 . ? C49 C50 1.511(3) . ? C50 H50A 0.9900 . ? C50 H50B 0.9900 . ? C50 C51 1.530(3) . ? C51 H51A 0.9900 . ? C51 H51B 0.9900 . ? C51 C52 1.518(3) . ? C52 H52A 0.9800 . ? C52 H52B 0.9800 . ? C52 H52C 0.9800 . ? C53 H53B 0.9900 . ? C53 H53A 0.9900 . ? C53 C54 1.523(3) . ? C54 H54B 0.9900 . ? C54 H54A 0.9900 . ? C54 C55 1.513(3) . ? C55 H55B 0.9900 . ? C55 H55A 0.9900 . ? C55 C56 1.529(4) . ? C56 H56C 0.9800 . ? C56 H56B 0.9800 . ? C56 H56A 0.9800 . ? C57 H57A 0.9900 . ? C57 H57B 0.9900 . ? C57 C58 1.535(13) . ? C57A H57D 0.9900 . ? C57A H57C 0.9900 . ? C57A C58A 1.532(15) . ? C58 H58A 0.9900 . ? C58 H58B 0.9900 . ? C58 C59 1.533(7) . ? C58A H58C 0.9900 . ? C58A H58D 0.9900 . ? C58A C59A 1.528(9) . ? C59 H59B 0.9900 . ? C59 H59A 0.9900 . ? C59 C60 1.511(6) . ? C59A H59D 0.9900 . ? C59A H59C 0.9900 . ? C59A C60A 1.512(8) . ? C60 H60A 0.9800 . ? C60 H60B 0.9800 . ? C60 H60C 0.9800 . ? C60A H60E 0.9800 . ? C60A H60D 0.9800 . ? C60A H60F 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag F1 C14 F2 106.36(17) . . ? F1 C14 C13 111.23(16) . . ? F2 C14 C13 112.51(16) . . ? F3 C14 F1 105.86(18) . . ? F3 C14 F2 105.53(17) . . ? F3 C14 C13 114.74(16) . . ? F4 C44 C43 110.59(17) . . ? F5 C44 F4 105.53(17) . . ? F5 C44 F6 106.23(17) . . ? F5 C44 C43 115.37(18) . . ? F6 C44 F4 105.42(18) . . ? F6 C44 C43 112.97(17) . . ? O1 C13 N3 133.50(18) . . ? O1 C13 C14 114.74(17) . . ? H2A O2 H2B 107(2) . . ? O3 C43 N7 133.6(2) . . ? O3 C43 C44 114.29(19) . . ? H4A O4 H4B 106.5(19) . . ? N1 C1 H1 117.7 . . ? N1 C1 C2 124.51(19) . . ? N1 C12 C4 122.55(18) . . ? N1 C12 C11 118.17(17) . . ? N2 C10 C9 123.82(19) . . ? N2 C10 H10 118.1 . . ? N2 C11 C7 122.71(18) . . ? N2 C11 C12 118.70(17) . . ? N3 C5 C4 114.25(17) . . ? N3 C13 C14 111.76(17) . . ? N4 C15 H15A 108.2 . . ? N4 C15 H15B 108.2 . . ? N4 C19 H19B 108.4 . . ? N4 C19 H19A 108.4 . . ? N4 C23 H23B 108.1 . . ? N4 C23 H23A 108.1 . . ? N4 C27 H27A 108.3 . . ? N4 C27 H27B 108.3 . . ? N5 C31 H31 118.1 . . ? N5 C31 C32 123.9(2) . . ? N5 C42 C34 122.74(19) . . ? N5 C42 C41 117.68(19) . . ? N6 C40 C39 123.8(2) . . ? N6 C40 H40 118.1 . . ? N6 C41 C37 123.36(19) . . ? N6 C41 C42 118.57(19) . . ? N7 C35 C34 114.27(18) . . ? N7 C43 C44 111.93(17) . . ? N8 C45 H45B 108.4 . . ? N8 C45 H45A 108.4 . . ? N8 C49 H49A 108.3 . . ? N8 C49 H49B 108.3 . . ? N8 C53 H53B 108.4 . . ? N8 C53 H53A 108.4 . . ? N8 C53 C54 115.45(18) . . ? N8 C57 H57A 108.5 . . ? N8 C57 H57B 108.5 . . ? N8 C57 C58 115.0(11) . . ? N8 C57A H57D 108.0 . . ? N8 C57A H57C 108.0 . . ? C1 N1 C12 117.31(18) . . ? C1 C2 H2 120.8 . . ? C2 C1 H1 117.7 . . ? C2 C3 H3 120.1 . . ? C2 C3 C4 119.71(19) . . ? C3 C2 C1 118.3(2) . . ? C3 C2 H2 120.8 . . ? C3 C4 C5 121.11(18) . . ? C3 C4 C12 117.57(18) . . ? C4 C3 H3 120.1 . . ? C4 C12 C11 119.27(17) . . ? C5 C6 H6 119.0 . . ? C5 C6 C7 121.94(18) . . ? C6 C5 N3 127.76(17) . . ? C6 C5 C4 117.98(17) . . ? C7 C6 H6 119.0 . . ? C7 C8 H8 120.3 . . ? C7 C11 C12 118.59(17) . . ? C8 C7 C6 121.65(18) . . ? C8 C7 C11 117.48(18) . . ? C8 C9 H9 120.6 . . ? C8 C9 C10 118.8(2) . . ? C9 C8 C7 119.4(2) . . ? C9 C8 H8 120.3 . . ? C9 C10 H10 118.1 . . ? C10 N2 C11 117.73(18) . . ? C10 C9 H9 120.6 . . ? C11 C7 C6 120.87(18) . . ? C12 C4 C5 121.32(18) . . ? C13 N3 C5 120.79(17) . . ? C15 N4 C19 110.89(15) . . ? C15 C16 H16A 109.7 . . ? C15 C16 H16B 109.7 . . ? C15 C16 C17 109.75(18) . . ? H15A C15 H15B 107.4 . . ? C16 C15 N4 116.29(16) . . ? C16 C15 H15A 108.2 . . ? C16 C15 H15B 108.2 . . ? C16 C17 H17A 108.9 . . ? C16 C17 H17B 108.9 . . ? H16A C16 H16B 108.2 . . ? C17 C16 H16A 109.7 . . ? C17 C16 H16B 109.7 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H17A C17 H17B 107.7 . . ? C18 C17 C16 113.2(2) . . ? C18 C17 H17A 108.9 . . ? C18 C17 H17B 108.9 . . ? H18A C18 H18B 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C19 C20 H20B 109.6 . . ? C19 C20 H20A 109.6 . . ? C19 C20 C21 110.18(18) . . ? H19B C19 H19A 107.4 . . ? C20 C19 N4 115.68(16) . . ? C20 C19 H19B 108.4 . . ? C20 C19 H19A 108.4 . . ? C20 C21 H21B 109.1 . . ? C20 C21 H21A 109.1 . . ? H20B C20 H20A 108.1 . . ? C21 C20 H20B 109.6 . . ? C21 C20 H20A 109.6 . . ? C21 C22 H22C 109.5 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H21B C21 H21A 107.8 . . ? C22 C21 C20 112.6(2) . . ? C22 C21 H21B 109.1 . . ? C22 C21 H21A 109.1 . . ? H22C C22 H22A 109.5 . . ? H22C C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C23 N4 C15 106.23(14) . . ? C23 N4 C19 111.40(15) . . ? C23 N4 C27 111.41(15) . . ? C23 C24 H24B 109.8 . . ? C23 C24 H24A 109.8 . . ? C23 C24 C25 109.38(17) . . ? H23B C23 H23A 107.3 . . ? C24 C23 N4 116.61(16) . . ? C24 C23 H23B 108.1 . . ? C24 C23 H23A 108.1 . . ? C24 C25 H25B 108.9 . . ? C24 C25 H25A 108.9 . . ? H24B C24 H24A 108.2 . . ? C25 C24 H24B 109.8 . . ? C25 C24 H24A 109.8 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26C 109.5 . . ? C25 C26 H26B 109.5 . . ? H25B C25 H25A 107.7 . . ? C26 C25 C24 113.55(18) . . ? C26 C25 H25B 108.9 . . ? C26 C25 H25A 108.9 . . ? H26A C26 H26C 109.5 . . ? H26A C26 H26B 109.5 . . ? H26C C26 H26B 109.5 . . ? C27 N4 C15 110.63(15) . . ? C27 N4 C19 106.36(15) . . ? C27 C28 H28A 109.7 . . ? C27 C28 H28B 109.7 . . ? C27 C28 C29 109.85(18) . . ? H27A C27 H27B 107.4 . . ? C28 C27 N4 115.83(16) . . ? C28 C27 H27A 108.3 . . ? C28 C27 H27B 108.3 . . ? C28 C29 H29A 109.0 . . ? C28 C29 H29B 109.0 . . ? H28A C28 H28B 108.2 . . ? C29 C28 H28A 109.7 . . ? C29 C28 H28B 109.7 . . ? C29 C30 H30C 109.5 . . ? C29 C30 H30A 109.5 . . ? C29 C30 H30B 109.5 . . ? H29A C29 H29B 107.8 . . ? C30 C29 C28 112.85(19) . . ? C30 C29 H29A 109.0 . . ? C30 C29 H29B 109.0 . . ? H30C C30 H30A 109.5 . . ? H30C C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C31 N5 C42 117.72(19) . . ? C31 C32 H32 120.7 . . ? C32 C31 H31 118.1 . . ? C32 C33 H33 120.0 . . ? C32 C33 C34 119.9(2) . . ? C33 C32 C31 118.6(2) . . ? C33 C32 H32 120.7 . . ? C33 C34 C35 121.66(19) . . ? C33 C34 C42 117.12(19) . . ? C34 C33 H33 120.0 . . ? C34 C42 C41 119.58(19) . . ? C35 C36 H36 119.0 . . ? C35 C36 C37 122.1(2) . . ? C36 C35 N7 127.9(2) . . ? C36 C35 C34 117.8(2) . . ? C37 C36 H36 119.0 . . ? C37 C38 H38 120.1 . . ? C37 C41 C42 118.07(19) . . ? C38 C37 C36 121.9(2) . . ? C38 C39 H39 120.6 . . ? C38 C39 C40 118.8(2) . . ? C39 C38 C37 119.7(2) . . ? C39 C38 H38 120.1 . . ? C39 C40 H40 118.1 . . ? C40 N6 C41 117.3(2) . . ? C40 C39 H39 120.6 . . ? C41 C37 C36 121.14(19) . . ? C41 C37 C38 117.0(2) . . ? C42 C34 C35 121.21(18) . . ? C43 N7 C35 121.61(18) . . ? C45 N8 C57A 106.3(5) . . ? C45 C46 H46A 109.6 . . ? C45 C46 H46B 109.6 . . ? H45B C45 H45A 107.5 . . ? C46 C45 N8 115.39(16) . . ? C46 C45 H45B 108.4 . . ? C46 C45 H45A 108.4 . . ? C46 C47 H47B 109.0 . . ? C46 C47 H47A 109.0 . . ? H46A C46 H46B 108.1 . . ? C47 C46 C45 110.30(18) . . ? C47 C46 H46A 109.6 . . ? C47 C46 H46B 109.6 . . ? C47 C48 H48B 109.5 . . ? C47 C48 H48C 109.5 . . ? C47 C48 H48A 109.5 . . ? H47B C47 H47A 107.8 . . ? C48 C47 C46 112.89(19) . . ? C48 C47 H47B 109.0 . . ? C48 C47 H47A 109.0 . . ? H48B C48 H48C 109.5 . . ? H48B C48 H48A 109.5 . . ? H48C C48 H48A 109.5 . . ? C49 N8 C45 110.87(15) . . ? C49 N8 C57A 111.1(6) . . ? C49 C50 H50A 109.8 . . ? C49 C50 H50B 109.8 . . ? C49 C50 C51 109.22(18) . . ? H49A C49 H49B 107.4 . . ? C50 C49 N8 115.95(17) . . ? C50 C49 H49A 108.3 . . ? C50 C49 H49B 108.3 . . ? C50 C51 H51A 109.0 . . ? C50 C51 H51B 109.0 . . ? H50A C50 H50B 108.3 . . ? C51 C50 H50A 109.8 . . ? C51 C50 H50B 109.8 . . ? C51 C52 H52A 109.5 . . ? C51 C52 H52B 109.5 . . ? C51 C52 H52C 109.5 . . ? H51A C51 H51B 107.8 . . ? C52 C51 C50 112.7(2) . . ? C52 C51 H51A 109.0 . . ? C52 C51 H51B 109.0 . . ? H52A C52 H52B 109.5 . . ? H52A C52 H52C 109.5 . . ? H52B C52 H52C 109.5 . . ? C53 N8 C45 106.74(15) . . ? C53 N8 C49 110.94(17) . . ? C53 N8 C57A 110.8(6) . . ? C53 C54 H54B 109.6 . . ? C53 C54 H54A 109.6 . . ? H53B C53 H53A 107.5 . . ? C54 C53 H53B 108.4 . . ? C54 C53 H53A 108.4 . . ? C54 C55 H55B 109.1 . . ? C54 C55 H55A 109.1 . . ? C54 C55 C56 112.4(2) . . ? H54B C54 H54A 108.1 . . ? C55 C54 C53 110.4(2) . . ? C55 C54 H54B 109.6 . . ? C55 C54 H54A 109.6 . . ? C55 C56 H56C 109.5 . . ? C55 C56 H56B 109.5 . . ? C55 C56 H56A 109.5 . . ? H55B C55 H55A 107.9 . . ? C56 C55 H55B 109.1 . . ? C56 C55 H55A 109.1 . . ? H56C C56 H56B 109.5 . . ? H56C C56 H56A 109.5 . . ? H56B C56 H56A 109.5 . . ? C57 N8 C45 116.3(6) . . ? C57 N8 C49 101.4(6) . . ? C57 N8 C53 110.6(7) . . ? C57 N8 C57A 11.4(10) . . ? C57 C58 H58A 109.8 . . ? C57 C58 H58B 109.8 . . ? H57A C57 H57B 107.5 . . ? C57A C58A H58C 109.9 . . ? C57A C58A H58D 109.9 . . ? H57D C57A H57C 107.2 . . ? C58 C57 H57A 108.5 . . ? C58 C57 H57B 108.5 . . ? C58 C59 H59B 108.8 . . ? C58 C59 H59A 108.8 . . ? H58A C58 H58B 108.2 . . ? C58A C57A N8 117.3(10) . . ? C58A C57A H57D 108.0 . . ? C58A C57A H57C 108.0 . . ? C58A C59A H59D 108.6 . . ? C58A C59A H59C 108.6 . . ? H58C C58A H58D 108.3 . . ? C59 C58 C57 109.5(7) . . ? C59 C58 H58A 109.8 . . ? C59 C58 H58B 109.8 . . ? H59B C59 H59A 107.7 . . ? C59A C58A C57A 109.0(7) . . ? C59A C58A H58C 109.9 . . ? C59A C58A H58D 109.9 . . ? C59A C60A H60E 109.5 . . ? C59A C60A H60D 109.5 . . ? C59A C60A H60F 109.5 . . ? H59D C59A H59C 107.6 . . ? C60 C59 C58 113.6(4) . . ? C60 C59 H59B 108.8 . . ? C60 C59 H59A 108.8 . . ? C60A C59A C58A 114.7(5) . . ? C60A C59A H59D 108.6 . . ? C60A C59A H59C 108.6 . . ? H60E C60A H60D 109.5 . . ? H60E C60A H60F 109.5 . . ? H60D C60A H60F 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2A O1 0.849(10) 1.988(11) 2.828(2) 170(3) . O2 H2B N5 0.852(10) 2.141(14) 2.941(3) 156(3) . O2 H2B N6 0.852(10) 2.56(2) 3.194(3) 133(2) . O4 H4A O3 0.848(10) 2.049(10) 2.896(2) 176(2) . O4 H4B N2 0.847(10) 2.300(19) 2.980(2) 138(2) 1_565