# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_TRZ-1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H23 F2 N5 O2 S' _chemical_formula_sum 'C26 H23 F2 N5 O2 S' _chemical_formula_weight 507.55 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.3326(3) _cell_length_b 13.4313(8) _cell_length_c 14.9364(8) _cell_angle_alpha 72.429(2) _cell_angle_beta 79.140(2) _cell_angle_gamma 89.112(2) _cell_volume 1188.29(11) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9867 _cell_measurement_theta_min 2.87 _cell_measurement_theta_max 30.56 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.419 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.187 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9512 _exptl_absorpt_correction_T_max 0.9815 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20226 _diffrn_reflns_av_R_equivalents 0.0589 _diffrn_reflns_av_sigmaI/netI 0.0407 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.46 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4110 _reflns_number_gt 3564 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0098P)^2^+1.8968P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4110 _refine_ls_number_parameters 325 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0748 _refine_ls_R_factor_gt 0.0636 _refine_ls_wR_factor_ref 0.1383 _refine_ls_wR_factor_gt 0.1325 _refine_ls_goodness_of_fit_ref 1.149 _refine_ls_restrained_S_all 1.149 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _iucr_refine_instructions_details ; TITL AF8 in P-1 CELL 0.71073 6.3326 13.4313 14.9364 72.429 79.140 89.112 ZERR 2.00 0.0003 0.0008 0.0008 0.002 0.002 0.002 LATT 1 SFAC C H N O F S UNIT 52 46 10 4 4 2 MERG 2 L.S. 12 TEMP -173 OMIT -1 50 ACTA BOND $H CONF ACTA SIZE 0.27 0.12 0.1 FMAP 2 PLAN 10 WGHT 0.009800 1.896800 FVAR 0.42440 S1 6 0.878104 1.116715 0.142577 11.00000 0.04365 0.03482 = 0.04668 -0.00376 -0.00414 -0.00486 F2 5 1.627606 0.660040 -0.018403 11.00000 0.07618 0.09749 = 0.07491 -0.03325 0.00717 0.04128 F1 5 0.266463 0.446535 0.439223 11.00000 0.04855 0.03281 = 0.05149 -0.00639 -0.00568 -0.00742 O1 4 0.360585 1.145022 0.532449 11.00000 0.06178 0.05283 = 0.03745 -0.01718 -0.00527 -0.00563 O2 4 0.691517 0.502565 0.376044 11.00000 0.04222 0.03344 = 0.03866 -0.01063 -0.01035 0.00818 N1 3 0.366200 1.160715 0.338989 11.00000 0.03373 0.03159 = 0.03661 -0.01218 -0.00854 0.00183 N2 3 0.490311 1.035403 0.250018 11.00000 0.03598 0.02847 = 0.03505 -0.01141 -0.00751 0.00267 N3 3 0.700835 0.915160 0.228279 11.00000 0.02879 0.03088 = 0.02967 -0.01089 -0.00414 0.00257 N4 3 0.373152 0.942517 0.296955 11.00000 0.03329 0.03110 = 0.03180 -0.01132 -0.00621 0.00220 N5 3 0.846845 0.855745 0.186630 11.00000 0.03116 0.03417 = 0.03125 -0.00997 -0.00037 0.00217 C1 1 0.526019 1.204474 0.458303 11.00000 0.04502 0.05463 = 0.04461 -0.02440 -0.00575 -0.00622 C2 1 0.566152 1.162291 0.373811 11.00000 0.03115 0.04031 = 0.04434 -0.01632 -0.00562 -0.00202 C3 1 0.198170 1.099365 0.415289 11.00000 0.03582 0.03797 = 0.05066 -0.01945 -0.00273 -0.00116 C4 1 0.167057 1.145499 0.497770 11.00000 0.04934 0.04195 = 0.05285 -0.02066 0.00405 -0.00355 C5 1 0.392061 1.136064 0.250742 11.00000 0.04444 0.03191 = 0.03697 -0.01127 -0.01437 0.00994 C6 1 0.692222 1.023179 0.207528 11.00000 0.03463 0.03227 = 0.03107 -0.01019 -0.00856 0.00108 C7 1 0.504341 0.870860 0.281617 11.00000 0.02928 0.03243 = 0.02763 -0.01155 -0.00643 0.00146 C8 1 1.042183 0.888197 0.156506 11.00000 0.03524 0.03569 = 0.03724 -0.01313 -0.00770 0.00023 C9 1 1.193766 0.826107 0.112002 11.00000 0.03354 0.04131 = 0.02778 -0.00852 -0.00322 0.00322 C10 1 1.402401 0.865499 0.072702 11.00000 0.03660 0.05350 = 0.03342 -0.00853 -0.00447 0.00048 C11 1 1.551031 0.809818 0.028672 11.00000 0.03506 0.08114 = 0.03751 -0.01127 -0.00091 0.01030 C12 1 1.485029 0.714666 0.026547 11.00000 0.04897 0.07005 = 0.04145 -0.01718 -0.00024 0.02754 C13 1 1.281660 0.670934 0.065989 11.00000 0.06735 0.04462 = 0.04674 -0.01619 -0.00667 0.01268 C14 1 1.134619 0.727579 0.109334 11.00000 0.04131 0.04241 = 0.03868 -0.00975 0.00031 0.00154 C15 1 0.446679 0.758241 0.320931 11.00000 0.03418 0.03000 = 0.02568 -0.01193 -0.00458 -0.00004 C16 1 0.600072 0.681920 0.328925 11.00000 0.02515 0.03683 = 0.03375 -0.01028 -0.00333 -0.00159 C17 1 0.538261 0.577792 0.367276 11.00000 0.03256 0.03358 = 0.02919 -0.01270 -0.00692 0.00516 C18 1 0.323234 0.549760 0.400049 11.00000 0.04039 0.03060 = 0.03036 -0.00893 -0.00528 -0.00452 C19 1 0.167920 0.622634 0.394293 11.00000 0.02958 0.04101 = 0.03687 -0.00955 0.00066 -0.00552 C20 1 0.230734 0.727247 0.353804 11.00000 0.03071 0.03568 = 0.03181 -0.01226 -0.00207 0.00245 C21 1 0.761951 0.468074 0.296635 11.00000 0.03736 0.02687 = 0.03799 -0.00836 -0.00340 -0.00003 C22 1 0.945348 0.412729 0.297529 11.00000 0.04005 0.03858 = 0.07074 -0.02080 -0.01643 0.00712 C23 1 1.026900 0.375599 0.221840 11.00000 0.04509 0.04657 = 0.09060 -0.03242 -0.00380 0.01338 C24 1 0.923640 0.393647 0.145779 11.00000 0.07242 0.05566 = 0.06349 -0.02846 0.00781 0.01321 C25 1 0.738770 0.448065 0.145856 11.00000 0.09354 0.07140 = 0.04679 -0.02873 -0.01599 0.03212 C26 1 0.657863 0.486949 0.221242 11.00000 0.05585 0.05962 = 0.05294 -0.02428 -0.01506 0.02791 H1A 2 0.660389 1.203098 0.483379 11.00000 -1.20000 H1B 2 0.484755 1.278076 0.437040 11.00000 -1.20000 H2A 2 0.677350 1.206998 0.322175 11.00000 -1.20000 H2B 2 0.619055 1.090667 0.393302 11.00000 -1.20000 H3A 2 0.239545 1.025841 0.437199 11.00000 -1.20000 H3B 2 0.062053 1.100579 0.391559 11.00000 -1.20000 H4A 2 0.120579 1.218146 0.475970 11.00000 -1.20000 H4B 2 0.052665 1.104309 0.550125 11.00000 -1.20000 H5A 2 0.481780 1.192886 0.200122 11.00000 -1.20000 H5B 2 0.248696 1.135634 0.233473 11.00000 -1.20000 H8 2 1.089094 0.952134 0.162863 11.00000 -1.20000 H10 2 1.444450 0.931720 0.075939 11.00000 -1.20000 H11 2 1.693991 0.837056 0.000932 11.00000 -1.20000 H13 2 1.242942 0.603850 0.063629 11.00000 -1.20000 H14 2 0.992547 0.699224 0.137445 11.00000 -1.20000 H16 2 0.748575 0.702175 0.307648 11.00000 -1.20000 H19 2 0.020180 0.601612 0.417666 11.00000 -1.20000 H20 2 0.124840 0.778493 0.348430 11.00000 -1.20000 H22 2 1.016515 0.399871 0.350261 11.00000 -1.20000 H23 2 1.154583 0.337526 0.222375 11.00000 -1.20000 H24 2 0.980007 0.368564 0.093427 11.00000 -1.20000 H25 2 0.665326 0.459304 0.093979 11.00000 -1.20000 H26 2 0.531729 0.526175 0.220380 11.00000 -1.20000 HKLF 4 END ; 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 S1 S 0.87810(14) 1.11671(6) 0.14258(6) 0.0442(2) Uani 1 1 d . . . F2 F 1.6276(4) 0.6600(2) -0.01840(19) 0.0847(8) Uani 1 1 d . . . F1 F 0.2665(3) 0.44654(13) 0.43922(14) 0.0462(5) Uani 1 1 d . . . O1 O 0.3606(4) 1.14502(19) 0.53245(16) 0.0504(6) Uani 1 1 d . . . O2 O 0.6915(3) 0.50257(16) 0.37604(15) 0.0379(5) Uani 1 1 d . . . N1 N 0.3662(4) 1.16071(19) 0.33899(18) 0.0333(6) Uani 1 1 d . . . N2 N 0.4903(4) 1.03540(18) 0.25002(17) 0.0327(6) Uani 1 1 d . . . N3 N 0.7008(4) 0.91516(18) 0.22828(17) 0.0296(5) Uani 1 1 d . . . N4 N 0.3732(4) 0.94252(18) 0.29695(17) 0.0317(5) Uani 1 1 d . . . N5 N 0.8468(4) 0.85575(19) 0.18663(17) 0.0330(6) Uani 1 1 d . . . C1 C 0.5260(5) 1.2045(3) 0.4583(2) 0.0463(8) Uani 1 1 d . . . H1A H 0.6604 1.2031 0.4834 0.056 Uiso 1 1 calc R . . H1B H 0.4848 1.2781 0.4370 0.056 Uiso 1 1 calc R . . C2 C 0.5662(5) 1.1623(2) 0.3738(2) 0.0380(7) Uani 1 1 d . . . H2A H 0.6773 1.2070 0.3222 0.046 Uiso 1 1 calc R . . H2B H 0.6191 1.0907 0.3933 0.046 Uiso 1 1 calc R . . C3 C 0.1982(5) 1.0994(2) 0.4153(2) 0.0409(7) Uani 1 1 d . . . H3A H 0.2395 1.0258 0.4372 0.049 Uiso 1 1 calc R . . H3B H 0.0621 1.1006 0.3916 0.049 Uiso 1 1 calc R . . C4 C 0.1671(6) 1.1455(3) 0.4978(3) 0.0485(9) Uani 1 1 d . . . H4A H 0.1206 1.2181 0.4760 0.058 Uiso 1 1 calc R . . H4B H 0.0527 1.1043 0.5501 0.058 Uiso 1 1 calc R . . C5 C 0.3921(5) 1.1361(2) 0.2507(2) 0.0368(7) Uani 1 1 d . . . H5A H 0.4818 1.1929 0.2001 0.044 Uiso 1 1 calc R . . H5B H 0.2487 1.1356 0.2335 0.044 Uiso 1 1 calc R . . C6 C 0.6922(5) 1.0232(2) 0.2075(2) 0.0322(6) Uani 1 1 d . . . C7 C 0.5043(4) 0.8709(2) 0.2816(2) 0.0291(6) Uani 1 1 d . . . C8 C 1.0422(5) 0.8882(2) 0.1565(2) 0.0355(7) Uani 1 1 d . . . H8 H 1.0891 0.9521 0.1629 0.043 Uiso 1 1 calc R . . C9 C 1.1938(5) 0.8261(2) 0.1120(2) 0.0350(7) Uani 1 1 d . . . C10 C 1.4024(5) 0.8655(3) 0.0727(2) 0.0425(8) Uani 1 1 d . . . H10 H 1.4445 0.9317 0.0759 0.051 Uiso 1 1 calc R . . C11 C 1.5510(6) 0.8098(3) 0.0287(2) 0.0537(10) Uani 1 1 d . . . H11 H 1.6940 0.8371 0.0009 0.064 Uiso 1 1 calc R . . C12 C 1.4850(6) 0.7147(3) 0.0265(3) 0.0549(10) Uani 1 1 d . . . C13 C 1.2817(6) 0.6709(3) 0.0660(3) 0.0531(9) Uani 1 1 d . . . H13 H 1.2429 0.6038 0.0636 0.064 Uiso 1 1 calc R . . C14 C 1.1346(5) 0.7276(3) 0.1093(2) 0.0425(8) Uani 1 1 d . . . H14 H 0.9925 0.6992 0.1374 0.051 Uiso 1 1 calc R . . C15 C 0.4467(5) 0.7582(2) 0.32093(19) 0.0293(6) Uani 1 1 d . . . C16 C 0.6001(4) 0.6819(2) 0.3289(2) 0.0323(6) Uani 1 1 d . . . H16 H 0.7486 0.7022 0.3076 0.039 Uiso 1 1 calc R . . C17 C 0.5383(5) 0.5778(2) 0.3673(2) 0.0310(6) Uani 1 1 d . . . C18 C 0.3232(5) 0.5498(2) 0.4000(2) 0.0340(7) Uani 1 1 d . . . C19 C 0.1679(5) 0.6226(2) 0.3943(2) 0.0372(7) Uani 1 1 d . . . H19 H 0.0202 0.6016 0.4177 0.045 Uiso 1 1 calc R . . C20 C 0.2307(5) 0.7272(2) 0.3538(2) 0.0328(6) Uani 1 1 d . . . H20 H 0.1248 0.7785 0.3484 0.039 Uiso 1 1 calc R . . C21 C 0.7620(5) 0.4681(2) 0.2966(2) 0.0349(7) Uani 1 1 d . . . C22 C 0.9453(5) 0.4127(3) 0.2975(3) 0.0481(9) Uani 1 1 d . . . H22 H 1.0165 0.3999 0.3503 0.058 Uiso 1 1 calc R . . C23 C 1.0269(6) 0.3756(3) 0.2218(3) 0.0595(11) Uani 1 1 d . . . H23 H 1.1546 0.3375 0.2224 0.071 Uiso 1 1 calc R . . C24 C 0.9236(7) 0.3936(3) 0.1458(3) 0.0645(11) Uani 1 1 d . . . H24 H 0.9800 0.3686 0.0934 0.077 Uiso 1 1 calc R . . C25 C 0.7388(8) 0.4481(3) 0.1459(3) 0.0681(12) Uani 1 1 d . . . H25 H 0.6653 0.4593 0.0940 0.082 Uiso 1 1 calc R . . C26 C 0.6579(6) 0.4869(3) 0.2212(3) 0.0542(9) Uani 1 1 d . . . H26 H 0.5317 0.5262 0.2204 0.065 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 S1 0.0436(5) 0.0348(4) 0.0467(5) -0.0038(4) -0.0041(4) -0.0049(3) F2 0.0762(17) 0.0975(19) 0.0749(17) -0.0333(15) 0.0072(13) 0.0413(15) F1 0.0486(11) 0.0328(10) 0.0515(11) -0.0064(8) -0.0057(9) -0.0074(8) O1 0.0618(16) 0.0528(14) 0.0375(13) -0.0172(11) -0.0053(11) -0.0056(12) O2 0.0422(12) 0.0334(11) 0.0387(12) -0.0106(9) -0.0103(9) 0.0082(9) N1 0.0337(13) 0.0316(13) 0.0366(14) -0.0122(11) -0.0085(11) 0.0018(10) N2 0.0360(14) 0.0285(13) 0.0350(14) -0.0114(11) -0.0075(11) 0.0027(10) N3 0.0288(12) 0.0309(13) 0.0297(13) -0.0109(10) -0.0041(10) 0.0026(10) N4 0.0333(13) 0.0311(13) 0.0318(13) -0.0113(11) -0.0062(10) 0.0022(10) N5 0.0312(13) 0.0342(13) 0.0313(13) -0.0100(11) -0.0004(10) 0.0022(10) C1 0.0450(19) 0.055(2) 0.0446(19) -0.0244(17) -0.0058(15) -0.0062(16) C2 0.0311(16) 0.0403(17) 0.0443(18) -0.0163(14) -0.0056(13) -0.0020(13) C3 0.0358(17) 0.0380(17) 0.051(2) -0.0194(15) -0.0027(14) -0.0012(13) C4 0.049(2) 0.0420(19) 0.053(2) -0.0207(16) 0.0040(16) -0.0035(15) C5 0.0444(18) 0.0319(16) 0.0370(17) -0.0113(13) -0.0144(14) 0.0099(13) C6 0.0346(16) 0.0323(16) 0.0311(15) -0.0102(12) -0.0086(12) 0.0011(12) C7 0.0293(15) 0.0324(15) 0.0276(15) -0.0116(12) -0.0064(11) 0.0015(12) C8 0.0352(17) 0.0357(16) 0.0372(17) -0.0131(13) -0.0077(13) 0.0002(13) C9 0.0335(16) 0.0413(17) 0.0278(15) -0.0085(13) -0.0032(12) 0.0032(13) C10 0.0366(17) 0.054(2) 0.0334(17) -0.0085(15) -0.0045(14) 0.0005(15) C11 0.0351(18) 0.081(3) 0.0375(19) -0.0113(18) -0.0009(14) 0.0103(18) C12 0.049(2) 0.070(3) 0.041(2) -0.0172(18) -0.0002(16) 0.0275(19) C13 0.067(2) 0.045(2) 0.047(2) -0.0162(17) -0.0067(18) 0.0127(18) C14 0.0413(18) 0.0424(19) 0.0387(18) -0.0097(15) 0.0003(14) 0.0015(14) C15 0.0342(15) 0.0300(15) 0.0257(14) -0.0119(12) -0.0046(12) 0.0000(12) C16 0.0252(14) 0.0368(16) 0.0338(16) -0.0103(13) -0.0033(12) -0.0016(12) C17 0.0326(15) 0.0336(16) 0.0292(15) -0.0127(12) -0.0069(12) 0.0052(12) C18 0.0404(17) 0.0306(15) 0.0304(16) -0.0089(13) -0.0053(13) -0.0045(13) C19 0.0296(15) 0.0410(17) 0.0369(17) -0.0095(14) 0.0007(13) -0.0055(13) C20 0.0307(15) 0.0357(16) 0.0318(16) -0.0123(13) -0.0021(12) 0.0025(12) C21 0.0374(17) 0.0269(15) 0.0380(17) -0.0084(13) -0.0034(13) 0.0000(12) C22 0.0401(18) 0.0386(18) 0.071(2) -0.0208(17) -0.0164(17) 0.0071(14) C23 0.045(2) 0.047(2) 0.091(3) -0.032(2) -0.004(2) 0.0134(17) C24 0.072(3) 0.056(2) 0.063(3) -0.028(2) 0.008(2) 0.013(2) C25 0.094(3) 0.071(3) 0.047(2) -0.029(2) -0.016(2) 0.032(2) C26 0.056(2) 0.060(2) 0.053(2) -0.0243(18) -0.0151(18) 0.0279(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C6 1.669(3) . ? F2 C12 1.361(4) . ? F1 C18 1.357(3) . ? O1 C1 1.420(4) . ? O1 C4 1.417(4) . ? O2 C17 1.385(3) . ? O2 C21 1.395(4) . ? N1 C5 1.433(4) . ? N1 C2 1.459(4) . ? N1 C3 1.454(4) . ? N2 C6 1.347(4) . ? N2 N4 1.379(3) . ? N2 C5 1.482(4) . ? N3 C7 1.378(4) . ? N3 C6 1.392(4) . ? N3 N5 1.392(3) . ? N4 C7 1.306(4) . ? N5 C8 1.269(4) . ? C1 C2 1.512(4) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.519(4) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C7 C15 1.472(4) . ? C8 C9 1.459(4) . ? C8 H8 0.9500 . ? C9 C10 1.383(4) . ? C9 C14 1.395(4) . ? C10 C11 1.385(5) . ? C10 H10 0.9500 . ? C11 C12 1.362(6) . ? C11 H11 0.9500 . ? C12 C13 1.371(5) . ? C13 C14 1.383(5) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C20 1.388(4) . ? C15 C16 1.396(4) . ? C16 C17 1.373(4) . ? C16 H16 0.9500 . ? C17 C18 1.374(4) . ? C18 C19 1.373(4) . ? C19 C20 1.383(4) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C21 C22 1.369(4) . ? C21 C26 1.367(5) . ? C22 C23 1.381(5) . ? C22 H22 0.9500 . ? C23 C24 1.373(6) . ? C23 H23 0.9500 . ? C24 C25 1.370(6) . ? C24 H24 0.9500 . ? C25 C26 1.390(5) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C4 110.2(3) . . ? C17 O2 C21 116.7(2) . . ? C5 N1 C2 114.0(2) . . ? C5 N1 C3 115.2(2) . . ? C2 N1 C3 110.5(2) . . ? C6 N2 N4 113.8(2) . . ? C6 N2 C5 126.2(2) . . ? N4 N2 C5 120.0(2) . . ? C7 N3 C6 108.2(2) . . ? C7 N3 N5 120.0(2) . . ? C6 N3 N5 129.8(2) . . ? C7 N4 N2 104.2(2) . . ? C8 N5 N3 119.5(2) . . ? O1 C1 C2 111.6(3) . . ? O1 C1 H1A 109.3 . . ? C2 C1 H1A 109.3 . . ? O1 C1 H1B 109.3 . . ? C2 C1 H1B 109.3 . . ? H1A C1 H1B 108.0 . . ? N1 C2 C1 109.3(3) . . ? N1 C2 H2A 109.8 . . ? C1 C2 H2A 109.8 . . ? N1 C2 H2B 109.8 . . ? C1 C2 H2B 109.8 . . ? H2A C2 H2B 108.3 . . ? N1 C3 C4 108.8(2) . . ? N1 C3 H3A 109.9 . . ? C4 C3 H3A 109.9 . . ? N1 C3 H3B 109.9 . . ? C4 C3 H3B 109.9 . . ? H3A C3 H3B 108.3 . . ? O1 C4 C3 110.8(3) . . ? O1 C4 H4A 109.5 . . ? C3 C4 H4A 109.5 . . ? O1 C4 H4B 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 108.1 . . ? N1 C5 N2 116.3(2) . . ? N1 C5 H5A 108.2 . . ? N2 C5 H5A 108.2 . . ? N1 C5 H5B 108.2 . . ? N2 C5 H5B 108.2 . . ? H5A C5 H5B 107.4 . . ? N2 C6 N3 102.7(2) . . ? N2 C6 S1 127.5(2) . . ? N3 C6 S1 129.7(2) . . ? N4 C7 N3 111.0(2) . . ? N4 C7 C15 123.0(3) . . ? N3 C7 C15 126.0(2) . . ? N5 C8 C9 119.2(3) . . ? N5 C8 H8 120.4 . . ? C9 C8 H8 120.4 . . ? C10 C9 C14 119.2(3) . . ? C10 C9 C8 119.0(3) . . ? C14 C9 C8 121.8(3) . . ? C9 C10 C11 121.0(3) . . ? C9 C10 H10 119.5 . . ? C11 C10 H10 119.5 . . ? C12 C11 C10 117.7(3) . . ? C12 C11 H11 121.2 . . ? C10 C11 H11 121.2 . . ? F2 C12 C11 118.4(4) . . ? F2 C12 C13 117.8(4) . . ? C11 C12 C13 123.8(3) . . ? C12 C13 C14 117.9(3) . . ? C12 C13 H13 121.1 . . ? C14 C13 H13 121.1 . . ? C13 C14 C9 120.4(3) . . ? C13 C14 H14 119.8 . . ? C9 C14 H14 119.8 . . ? C20 C15 C16 118.9(3) . . ? C20 C15 C7 118.3(3) . . ? C16 C15 C7 122.8(3) . . ? C17 C16 C15 120.6(3) . . ? C17 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? C18 C17 O2 120.6(3) . . ? C18 C17 C16 119.1(3) . . ? O2 C17 C16 120.3(3) . . ? F1 C18 C17 118.0(3) . . ? F1 C18 C19 120.0(3) . . ? C17 C18 C19 122.0(3) . . ? C18 C19 C20 118.7(3) . . ? C18 C19 H19 120.7 . . ? C20 C19 H19 120.7 . . ? C19 C20 C15 120.8(3) . . ? C19 C20 H20 119.6 . . ? C15 C20 H20 119.6 . . ? C22 C21 C26 120.5(3) . . ? C22 C21 O2 116.1(3) . . ? C26 C21 O2 123.4(3) . . ? C21 C22 C23 120.0(4) . . ? C21 C22 H22 120.0 . . ? C23 C22 H22 120.0 . . ? C24 C23 C22 120.1(3) . . ? C24 C23 H23 120.0 . . ? C22 C23 H23 120.0 . . ? C23 C24 C25 119.6(4) . . ? C23 C24 H24 120.2 . . ? C25 C24 H24 120.2 . . ? C24 C25 C26 120.5(4) . . ? C24 C25 H25 119.7 . . ? C26 C25 H25 119.7 . . ? C21 C26 C25 119.2(3) . . ? C21 C26 H26 120.4 . . ? C25 C26 H26 120.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 N2 N4 C7 -1.2(3) . . . . ? C5 N2 N4 C7 179.5(2) . . . . ? C7 N3 N5 C8 -164.2(3) . . . . ? C6 N3 N5 C8 33.8(4) . . . . ? C4 O1 C1 C2 -58.6(4) . . . . ? C5 N1 C2 C1 171.6(3) . . . . ? C3 N1 C2 C1 -56.8(3) . . . . ? O1 C1 C2 N1 56.9(4) . . . . ? C5 N1 C3 C4 -171.2(3) . . . . ? C2 N1 C3 C4 57.8(3) . . . . ? C1 O1 C4 C3 59.6(3) . . . . ? N1 C3 C4 O1 -59.2(4) . . . . ? C2 N1 C5 N2 57.1(3) . . . . ? C3 N1 C5 N2 -72.2(3) . . . . ? C6 N2 C5 N1 -105.8(3) . . . . ? N4 N2 C5 N1 73.4(3) . . . . ? N4 N2 C6 N3 0.8(3) . . . . ? C5 N2 C6 N3 -180.0(2) . . . . ? N4 N2 C6 S1 178.5(2) . . . . ? C5 N2 C6 S1 -2.3(4) . . . . ? C7 N3 C6 N2 -0.1(3) . . . . ? N5 N3 C6 N2 163.5(3) . . . . ? C7 N3 C6 S1 -177.7(2) . . . . ? N5 N3 C6 S1 -14.1(5) . . . . ? N2 N4 C7 N3 1.1(3) . . . . ? N2 N4 C7 C15 178.7(2) . . . . ? C6 N3 C7 N4 -0.7(3) . . . . ? N5 N3 C7 N4 -166.2(2) . . . . ? C6 N3 C7 C15 -178.1(3) . . . . ? N5 N3 C7 C15 16.3(4) . . . . ? N3 N5 C8 C9 -179.3(2) . . . . ? N5 C8 C9 C10 175.1(3) . . . . ? N5 C8 C9 C14 -5.9(5) . . . . ? C14 C9 C10 C11 1.7(5) . . . . ? C8 C9 C10 C11 -179.2(3) . . . . ? C9 C10 C11 C12 -0.8(5) . . . . ? C10 C11 C12 F2 178.5(3) . . . . ? C10 C11 C12 C13 -0.6(6) . . . . ? F2 C12 C13 C14 -178.2(3) . . . . ? C11 C12 C13 C14 0.9(6) . . . . ? C12 C13 C14 C9 0.2(5) . . . . ? C10 C9 C14 C13 -1.4(5) . . . . ? C8 C9 C14 C13 179.5(3) . . . . ? N4 C7 C15 C20 17.3(4) . . . . ? N3 C7 C15 C20 -165.5(3) . . . . ? N4 C7 C15 C16 -160.9(3) . . . . ? N3 C7 C15 C16 16.3(4) . . . . ? C20 C15 C16 C17 1.0(4) . . . . ? C7 C15 C16 C17 179.1(3) . . . . ? C21 O2 C17 C18 96.0(3) . . . . ? C21 O2 C17 C16 -86.5(3) . . . . ? C15 C16 C17 C18 -1.7(4) . . . . ? C15 C16 C17 O2 -179.2(2) . . . . ? O2 C17 C18 F1 -1.3(4) . . . . ? C16 C17 C18 F1 -178.8(3) . . . . ? O2 C17 C18 C19 178.5(3) . . . . ? C16 C17 C18 C19 1.0(4) . . . . ? F1 C18 C19 C20 -179.9(3) . . . . ? C17 C18 C19 C20 0.3(5) . . . . ? C18 C19 C20 C15 -1.0(4) . . . . ? C16 C15 C20 C19 0.3(4) . . . . ? C7 C15 C20 C19 -177.9(3) . . . . ? C17 O2 C21 C22 165.6(3) . . . . ? C17 O2 C21 C26 -14.4(4) . . . . ? C26 C21 C22 C23 0.1(5) . . . . ? O2 C21 C22 C23 -179.9(3) . . . . ? C21 C22 C23 C24 -0.3(6) . . . . ? C22 C23 C24 C25 -0.4(6) . . . . ? C23 C24 C25 C26 1.4(7) . . . . ? C22 C21 C26 C25 0.9(6) . . . . ? O2 C21 C26 C25 -179.1(3) . . . . ? C24 C25 C26 C21 -1.6(7) . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.375 _refine_diff_density_min -0.251 _refine_diff_density_rms 0.054 _database_code_depnum_ccdc_archive 'CCDC 963711' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_shelxl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H23 Cl F N5 O2 S' _chemical_formula_sum 'C26 H23 Cl F N5 O2 S' _chemical_formula_weight 524.00 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.2030(5) _cell_length_b 13.8341(12) _cell_length_c 15.1090(14) _cell_angle_alpha 71.303(4) _cell_angle_beta 80.718(4) _cell_angle_gamma 88.344(4) _cell_volume 1211.68(18) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9888 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 30.54 _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.436 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.287 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.8939 _exptl_absorpt_correction_T_max 0.9449 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18352 _diffrn_reflns_av_R_equivalents 0.0469 _diffrn_reflns_av_sigmaI/netI 0.0358 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.44 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4264 _reflns_number_gt 3955 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0527P)^2^+0.4261P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4264 _refine_ls_number_parameters 325 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0369 _refine_ls_R_factor_gt 0.0347 _refine_ls_wR_factor_ref 0.0958 _refine_ls_wR_factor_gt 0.0936 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _iucr_refine_instructions_details ; TITL TRZ-2_Form I in P-1 CELL 0.71073 6.2030 13.8341 15.1090 71.303 80.718 88.344 ZERR 2.00 0.0005 0.0012 0.0014 0.004 0.004 0.004 LATT 1 SFAC C H N O F S CL UNIT 52 46 10 4 2 2 2 MERG 2 L.S. 12 ACTA BOND $H OMIT -1 50 CONF SIZE 0.2 0.2 0.4 TEMP -173 FMAP 2 PLAN 10 WGHT 0.052700 0.426100 FVAR 0.16451 S1 6 0.361802 1.114366 0.142716 11.00000 0.02540 0.02231 = 0.02700 -0.00197 0.00019 -0.00452 CL1 7 1.193577 0.662811 -0.021283 11.00000 0.03357 0.04298 = 0.03207 -0.01501 0.00414 0.00992 F1 5 -0.228429 0.458100 0.439625 11.00000 0.02860 0.02112 = 0.02901 -0.00534 0.00105 -0.00688 O1 4 -0.158806 1.146922 0.529720 11.00000 0.03525 0.03950 = 0.02243 -0.01093 0.00300 -0.00786 O2 4 0.202873 0.513444 0.376012 11.00000 0.02497 0.02132 = 0.02483 -0.00836 -0.00355 0.00394 N1 3 -0.150440 1.156979 0.338962 11.00000 0.02012 0.02157 = 0.02209 -0.00688 -0.00194 -0.00077 N2 3 -0.019887 1.034057 0.255267 11.00000 0.02162 0.01890 = 0.02119 -0.00549 -0.00129 -0.00089 N3 3 0.195809 0.917155 0.233139 11.00000 0.01799 0.01907 = 0.01847 -0.00563 -0.00066 -0.00058 N4 3 -0.132586 0.942862 0.302532 11.00000 0.02136 0.02002 = 0.02021 -0.00593 -0.00148 -0.00155 N5 3 0.342146 0.859769 0.191791 11.00000 0.02126 0.02236 = 0.01730 -0.00606 0.00094 0.00119 C1 1 0.009797 1.203500 0.456442 11.00000 0.03143 0.04213 = 0.02700 -0.01389 0.00059 -0.01186 C2 1 0.052352 1.158526 0.376111 11.00000 0.02110 0.03248 = 0.02321 -0.00884 -0.00025 -0.00506 C3 1 -0.319889 1.097808 0.414560 11.00000 0.01865 0.02770 = 0.03061 -0.01107 0.00199 -0.00244 C4 1 -0.353637 1.146284 0.492265 11.00000 0.02743 0.03167 = 0.03177 -0.01365 0.00655 -0.00403 C5 1 -0.124408 1.132390 0.253061 11.00000 0.02598 0.02070 = 0.02297 -0.00589 -0.00618 0.00391 C6 1 0.182119 1.022517 0.211105 11.00000 0.02257 0.02215 = 0.01832 -0.00689 -0.00498 -0.00010 C7 1 -0.000355 0.872927 0.287848 11.00000 0.01795 0.02295 = 0.01606 -0.00686 -0.00224 -0.00040 C8 1 0.538836 0.893440 0.161270 11.00000 0.02204 0.02458 = 0.02006 -0.00674 -0.00298 -0.00149 C9 1 0.693763 0.834231 0.116933 11.00000 0.02193 0.02734 = 0.01493 -0.00464 -0.00202 0.00027 C10 1 0.904395 0.875195 0.078594 11.00000 0.02286 0.02881 = 0.01824 -0.00622 -0.00210 -0.00175 C11 1 1.058741 0.822817 0.035878 11.00000 0.02012 0.03764 = 0.01975 -0.00661 0.00011 -0.00071 C12 1 1.000570 0.728495 0.032735 11.00000 0.02723 0.03487 = 0.01768 -0.00679 -0.00195 0.00730 C13 1 0.793038 0.685299 0.070976 11.00000 0.03065 0.02638 = 0.02425 -0.00738 -0.00110 0.00086 C14 1 0.639781 0.738771 0.112505 11.00000 0.02248 0.02773 = 0.02152 -0.00482 0.00127 -0.00223 C15 1 -0.054498 0.763326 0.326264 11.00000 0.02101 0.02182 = 0.01433 -0.00650 -0.00173 -0.00196 C16 1 0.103480 0.688658 0.331808 11.00000 0.01863 0.02350 = 0.01914 -0.00720 -0.00019 -0.00223 C17 1 0.043104 0.586554 0.369321 11.00000 0.02145 0.02318 = 0.01770 -0.00831 -0.00250 0.00174 C18 1 -0.173543 0.558852 0.403138 11.00000 0.02688 0.01963 = 0.01668 -0.00511 -0.00102 -0.00488 C19 1 -0.333330 0.630586 0.399502 11.00000 0.01915 0.02863 = 0.01946 -0.00659 0.00149 -0.00393 C20 1 -0.273440 0.733000 0.360528 11.00000 0.01971 0.02559 = 0.01769 -0.00736 -0.00077 0.00220 C21 1 0.241053 0.469872 0.303707 11.00000 0.02405 0.01665 = 0.02257 -0.00538 0.00420 -0.00426 C22 1 0.428770 0.413293 0.302090 11.00000 0.02320 0.02496 = 0.03857 -0.00974 -0.00138 -0.00061 C23 1 0.477991 0.366040 0.233257 11.00000 0.02994 0.02832 = 0.04768 -0.01501 0.00579 0.00330 C24 1 0.340619 0.374875 0.167785 11.00000 0.04302 0.02961 = 0.03283 -0.01516 0.00844 -0.00181 C25 1 0.154059 0.431269 0.170647 11.00000 0.04331 0.03448 = 0.02687 -0.01208 -0.00332 0.00090 C26 1 0.102869 0.479668 0.238692 11.00000 0.03040 0.02886 = 0.02642 -0.00944 -0.00180 0.00561 H1A 2 0.145856 1.202848 0.483014 11.00000 -1.20000 H1B 2 -0.033930 1.275346 0.431703 11.00000 -1.20000 H2A 2 0.165456 1.200177 0.325265 11.00000 -1.20000 H2B 2 0.106218 1.088267 0.399405 11.00000 -1.20000 H3A 2 -0.274307 1.026325 0.439784 11.00000 -1.20000 H3B 2 -0.457935 1.097601 0.389625 11.00000 -1.20000 H4A 2 -0.402109 1.217217 0.466658 11.00000 -1.20000 H4B 2 -0.469869 1.107890 0.543530 11.00000 -1.20000 H5A 2 -0.036440 1.187819 0.202762 11.00000 -1.20000 H5B 2 -0.270463 1.131533 0.234825 11.00000 -1.20000 H8 2 0.583755 0.955820 0.167248 11.00000 -1.20000 H10 2 0.942286 0.939871 0.081866 11.00000 -1.20000 H11 2 1.201426 0.851139 0.009336 11.00000 -1.20000 H13 2 0.757079 0.619985 0.068600 11.00000 -1.20000 H14 2 0.496808 0.710419 0.138204 11.00000 -1.20000 H16 2 0.253108 0.708155 0.309689 11.00000 -1.20000 H19 2 -0.482000 0.610174 0.423308 11.00000 -1.20000 H20 2 -0.382308 0.783228 0.357026 11.00000 -1.20000 H22 2 0.522437 0.406951 0.347476 11.00000 -1.20000 H23 2 0.606764 0.327426 0.231134 11.00000 -1.20000 H24 2 0.374538 0.342191 0.120892 11.00000 -1.20000 H25 2 0.059658 0.437064 0.125642 11.00000 -1.20000 H26 2 -0.025181 0.518832 0.240358 11.00000 -1.20000 HKLF 4 END ; 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 S1 S 0.36180(6) 1.11437(3) 0.14272(3) 0.02674(12) Uani 1 1 d . . . Cl1 Cl 1.19358(7) 0.66281(3) -0.02128(3) 0.03676(14) Uani 1 1 d . . . F1 F -0.22843(14) 0.45810(6) 0.43963(6) 0.0274(2) Uani 1 1 d . . . O1 O -0.15881(19) 1.14692(9) 0.52972(8) 0.0329(3) Uani 1 1 d . . . O2 O 0.20287(16) 0.51344(8) 0.37601(7) 0.0236(2) Uani 1 1 d . . . N1 N -0.15044(19) 1.15698(9) 0.33896(9) 0.0214(3) Uani 1 1 d . . . N2 N -0.01989(19) 1.03406(9) 0.25527(9) 0.0210(3) Uani 1 1 d . . . N3 N 0.19581(19) 0.91715(9) 0.23314(8) 0.0188(3) Uani 1 1 d . . . N4 N -0.13259(19) 0.94286(9) 0.30253(8) 0.0208(3) Uani 1 1 d . . . N5 N 0.34215(19) 0.85977(9) 0.19179(8) 0.0209(3) Uani 1 1 d . . . C1 C 0.0098(3) 1.20350(14) 0.45644(12) 0.0332(4) Uani 1 1 d . . . H1A H 0.1459 1.2028 0.4830 0.040 Uiso 1 1 calc R . . H1B H -0.0339 1.2753 0.4317 0.040 Uiso 1 1 calc R . . C2 C 0.0524(2) 1.15853(13) 0.37611(11) 0.0259(3) Uani 1 1 d . . . H2A H 0.1655 1.2002 0.3253 0.031 Uiso 1 1 calc R . . H2B H 0.1062 1.0883 0.3994 0.031 Uiso 1 1 calc R . . C3 C -0.3199(2) 1.09781(12) 0.41456(11) 0.0259(3) Uani 1 1 d . . . H3A H -0.2743 1.0263 0.4398 0.031 Uiso 1 1 calc R . . H3B H -0.4579 1.0976 0.3896 0.031 Uiso 1 1 calc R . . C4 C -0.3536(3) 1.14628(13) 0.49227(12) 0.0307(4) Uani 1 1 d . . . H4A H -0.4021 1.2172 0.4667 0.037 Uiso 1 1 calc R . . H4B H -0.4699 1.1079 0.5435 0.037 Uiso 1 1 calc R . . C5 C -0.1244(2) 1.13239(11) 0.25306(10) 0.0233(3) Uani 1 1 d . . . H5A H -0.0364 1.1878 0.2028 0.028 Uiso 1 1 calc R . . H5B H -0.2705 1.1315 0.2348 0.028 Uiso 1 1 calc R . . C6 C 0.1821(2) 1.02252(11) 0.21111(10) 0.0207(3) Uani 1 1 d . . . C7 C -0.0004(2) 0.87293(11) 0.28785(10) 0.0189(3) Uani 1 1 d . . . C8 C 0.5388(2) 0.89344(12) 0.16127(10) 0.0223(3) Uani 1 1 d . . . H8 H 0.5838 0.9558 0.1672 0.027 Uiso 1 1 calc R . . C9 C 0.6938(2) 0.83423(12) 0.11693(10) 0.0220(3) Uani 1 1 d . . . C10 C 0.9044(2) 0.87520(12) 0.07859(10) 0.0237(3) Uani 1 1 d . . . H10 H 0.9423 0.9399 0.0819 0.028 Uiso 1 1 calc R . . C11 C 1.0587(2) 0.82282(13) 0.03588(10) 0.0268(3) Uani 1 1 d . . . H11 H 1.2014 0.8511 0.0093 0.032 Uiso 1 1 calc R . . C12 C 1.0006(3) 0.72850(13) 0.03274(11) 0.0273(3) Uani 1 1 d . . . C13 C 0.7930(3) 0.68530(12) 0.07098(11) 0.0277(3) Uani 1 1 d . . . H13 H 0.7571 0.6200 0.0686 0.033 Uiso 1 1 calc R . . C14 C 0.6398(2) 0.73877(12) 0.11251(11) 0.0252(3) Uani 1 1 d . . . H14 H 0.4968 0.7104 0.1382 0.030 Uiso 1 1 calc R . . C15 C -0.0545(2) 0.76333(11) 0.32626(10) 0.0190(3) Uani 1 1 d . . . C16 C 0.1035(2) 0.68866(11) 0.33181(10) 0.0206(3) Uani 1 1 d . . . H16 H 0.2531 0.7082 0.3097 0.025 Uiso 1 1 calc R . . C17 C 0.0431(2) 0.58655(11) 0.36932(10) 0.0204(3) Uani 1 1 d . . . C18 C -0.1735(2) 0.55885(11) 0.40314(10) 0.0214(3) Uani 1 1 d . . . C19 C -0.3333(2) 0.63059(12) 0.39950(10) 0.0231(3) Uani 1 1 d . . . H19 H -0.4820 0.6102 0.4233 0.028 Uiso 1 1 calc R . . C20 C -0.2734(2) 0.73300(11) 0.36053(10) 0.0212(3) Uani 1 1 d . . . H20 H -0.3823 0.7832 0.3570 0.025 Uiso 1 1 calc R . . C21 C 0.2411(2) 0.46987(11) 0.30371(10) 0.0221(3) Uani 1 1 d . . . C22 C 0.4288(3) 0.41329(12) 0.30209(12) 0.0294(4) Uani 1 1 d . . . H22 H 0.5224 0.4070 0.3475 0.035 Uiso 1 1 calc R . . C23 C 0.4780(3) 0.36604(13) 0.23326(13) 0.0361(4) Uani 1 1 d . . . H23 H 0.6068 0.3274 0.2311 0.043 Uiso 1 1 calc R . . C24 C 0.3406(3) 0.37488(13) 0.16778(12) 0.0355(4) Uani 1 1 d . . . H24 H 0.3745 0.3422 0.1209 0.043 Uiso 1 1 calc R . . C25 C 0.1541(3) 0.43127(13) 0.17065(12) 0.0346(4) Uani 1 1 d . . . H25 H 0.0597 0.4371 0.1256 0.042 Uiso 1 1 calc R . . C26 C 0.1029(3) 0.47967(12) 0.23869(11) 0.0288(4) Uani 1 1 d . . . H26 H -0.0252 0.5188 0.2404 0.035 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 S1 0.0254(2) 0.0223(2) 0.0270(2) -0.00197(16) 0.00019(15) -0.00452(15) Cl1 0.0336(2) 0.0430(3) 0.0321(2) -0.01501(19) 0.00414(17) 0.00992(18) F1 0.0286(5) 0.0211(5) 0.0290(5) -0.0053(4) 0.0011(4) -0.0069(4) O1 0.0353(6) 0.0395(7) 0.0224(6) -0.0109(5) 0.0030(5) -0.0079(5) O2 0.0250(5) 0.0213(5) 0.0248(5) -0.0084(4) -0.0035(4) 0.0039(4) N1 0.0201(6) 0.0216(6) 0.0221(6) -0.0069(5) -0.0019(5) -0.0008(5) N2 0.0216(6) 0.0189(6) 0.0212(6) -0.0055(5) -0.0013(5) -0.0009(5) N3 0.0180(6) 0.0191(6) 0.0185(6) -0.0056(5) -0.0007(5) -0.0006(5) N4 0.0214(6) 0.0200(6) 0.0202(6) -0.0059(5) -0.0015(5) -0.0015(5) N5 0.0213(6) 0.0224(6) 0.0173(6) -0.0061(5) 0.0009(5) 0.0012(5) C1 0.0314(9) 0.0421(10) 0.0270(8) -0.0139(7) 0.0006(7) -0.0119(7) C2 0.0211(7) 0.0325(9) 0.0232(8) -0.0088(7) -0.0002(6) -0.0051(6) C3 0.0187(7) 0.0277(8) 0.0306(8) -0.0111(7) 0.0020(6) -0.0024(6) C4 0.0274(8) 0.0317(9) 0.0318(9) -0.0137(7) 0.0065(7) -0.0040(6) C5 0.0260(8) 0.0207(7) 0.0230(8) -0.0059(6) -0.0062(6) 0.0039(6) C6 0.0226(7) 0.0221(7) 0.0183(7) -0.0069(6) -0.0050(6) -0.0001(6) C7 0.0180(7) 0.0230(8) 0.0161(7) -0.0069(6) -0.0022(5) -0.0004(5) C8 0.0220(7) 0.0246(8) 0.0201(7) -0.0067(6) -0.0030(6) -0.0015(6) C9 0.0219(7) 0.0273(8) 0.0149(7) -0.0046(6) -0.0020(5) 0.0003(6) C10 0.0229(7) 0.0288(8) 0.0182(7) -0.0062(6) -0.0021(6) -0.0017(6) C11 0.0201(7) 0.0376(9) 0.0198(7) -0.0066(7) 0.0001(6) -0.0007(6) C12 0.0272(8) 0.0349(9) 0.0177(7) -0.0068(6) -0.0020(6) 0.0073(6) C13 0.0306(8) 0.0264(8) 0.0243(8) -0.0074(6) -0.0011(6) 0.0009(6) C14 0.0225(7) 0.0277(8) 0.0215(7) -0.0048(6) 0.0013(6) -0.0022(6) C15 0.0210(7) 0.0218(7) 0.0143(7) -0.0065(6) -0.0017(5) -0.0020(5) C16 0.0186(7) 0.0235(8) 0.0191(7) -0.0072(6) -0.0002(5) -0.0022(6) C17 0.0214(7) 0.0232(8) 0.0177(7) -0.0083(6) -0.0025(5) 0.0017(6) C18 0.0269(8) 0.0196(7) 0.0167(7) -0.0051(6) -0.0010(6) -0.0049(6) C19 0.0191(7) 0.0286(8) 0.0195(7) -0.0066(6) 0.0015(6) -0.0039(6) C20 0.0197(7) 0.0256(8) 0.0177(7) -0.0074(6) -0.0008(5) 0.0022(6) C21 0.0241(7) 0.0167(7) 0.0226(7) -0.0054(6) 0.0042(6) -0.0043(6) C22 0.0232(8) 0.0250(8) 0.0386(9) -0.0097(7) -0.0014(7) -0.0006(6) C23 0.0299(9) 0.0283(9) 0.0477(11) -0.0150(8) 0.0058(8) 0.0033(7) C24 0.0430(10) 0.0296(9) 0.0328(9) -0.0152(7) 0.0084(7) -0.0018(7) C25 0.0433(10) 0.0345(9) 0.0269(8) -0.0121(7) -0.0033(7) 0.0009(7) C26 0.0304(8) 0.0289(8) 0.0264(8) -0.0094(7) -0.0018(6) 0.0056(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C6 1.6713(15) . ? Cl1 C12 1.7386(15) . ? F1 C18 1.3553(17) . ? O1 C4 1.416(2) . ? O1 C1 1.4319(19) . ? O2 C17 1.3871(17) . ? O2 C21 1.3940(18) . ? N1 C5 1.4278(19) . ? N1 C2 1.4611(19) . ? N1 C3 1.4637(19) . ? N2 C6 1.3520(19) . ? N2 N4 1.3794(17) . ? N2 C5 1.4829(19) . ? N3 C7 1.3902(18) . ? N3 C6 1.3905(19) . ? N3 N5 1.3921(16) . ? N4 C7 1.3004(19) . ? N5 C8 1.2774(19) . ? C1 C2 1.517(2) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.513(2) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C7 C15 1.467(2) . ? C8 C9 1.464(2) . ? C8 H8 0.9500 . ? C9 C14 1.396(2) . ? C9 C10 1.397(2) . ? C10 C11 1.385(2) . ? C10 H10 0.9500 . ? C11 C12 1.381(2) . ? C11 H11 0.9500 . ? C12 C13 1.390(2) . ? C13 C14 1.382(2) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C16 1.395(2) . ? C15 C20 1.398(2) . ? C16 C17 1.380(2) . ? C16 H16 0.9500 . ? C17 C18 1.377(2) . ? C18 C19 1.377(2) . ? C19 C20 1.385(2) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C21 C26 1.378(2) . ? C21 C22 1.385(2) . ? C22 C23 1.387(2) . ? C22 H22 0.9500 . ? C23 C24 1.381(3) . ? C23 H23 0.9500 . ? C24 C25 1.379(3) . ? C24 H24 0.9500 . ? C25 C26 1.389(2) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? 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 C4 O1 C1 109.91(12) . . ? C17 O2 C21 116.86(11) . . ? C5 N1 C2 114.46(12) . . ? C5 N1 C3 115.55(12) . . ? C2 N1 C3 110.01(12) . . ? C6 N2 N4 113.40(12) . . ? C6 N2 C5 126.10(12) . . ? N4 N2 C5 120.45(11) . . ? C7 N3 C6 108.33(11) . . ? C7 N3 N5 120.00(11) . . ? C6 N3 N5 129.58(11) . . ? C7 N4 N2 105.06(11) . . ? C8 N5 N3 118.32(12) . . ? O1 C1 C2 111.17(13) . . ? O1 C1 H1A 109.4 . . ? C2 C1 H1A 109.4 . . ? O1 C1 H1B 109.4 . . ? C2 C1 H1B 109.4 . . ? H1A C1 H1B 108.0 . . ? N1 C2 C1 109.16(13) . . ? N1 C2 H2A 109.8 . . ? C1 C2 H2A 109.8 . . ? N1 C2 H2B 109.8 . . ? C1 C2 H2B 109.8 . . ? H2A C2 H2B 108.3 . . ? N1 C3 C4 108.33(12) . . ? N1 C3 H3A 110.0 . . ? C4 C3 H3A 110.0 . . ? N1 C3 H3B 110.0 . . ? C4 C3 H3B 110.0 . . ? H3A C3 H3B 108.4 . . ? O1 C4 C3 111.22(13) . . ? O1 C4 H4A 109.4 . . ? C3 C4 H4A 109.4 . . ? O1 C4 H4B 109.4 . . ? C3 C4 H4B 109.4 . . ? H4A C4 H4B 108.0 . . ? N1 C5 N2 116.33(12) . . ? N1 C5 H5A 108.2 . . ? N2 C5 H5A 108.2 . . ? N1 C5 H5B 108.2 . . ? N2 C5 H5B 108.2 . . ? H5A C5 H5B 107.4 . . ? N2 C6 N3 102.81(12) . . ? N2 C6 S1 127.53(11) . . ? N3 C6 S1 129.60(11) . . ? N4 C7 N3 110.39(12) . . ? N4 C7 C15 123.50(13) . . ? N3 C7 C15 126.09(12) . . ? N5 C8 C9 118.84(14) . . ? N5 C8 H8 120.6 . . ? C9 C8 H8 120.6 . . ? C14 C9 C10 119.21(14) . . ? C14 C9 C8 122.66(13) . . ? C10 C9 C8 118.12(14) . . ? C11 C10 C9 120.92(15) . . ? C11 C10 H10 119.5 . . ? C9 C10 H10 119.5 . . ? C12 C11 C10 118.52(14) . . ? C12 C11 H11 120.7 . . ? C10 C11 H11 120.7 . . ? C11 C12 C13 121.93(14) . . ? C11 C12 Cl1 118.62(12) . . ? C13 C12 Cl1 119.44(13) . . ? C14 C13 C12 119.01(15) . . ? C14 C13 H13 120.5 . . ? C12 C13 H13 120.5 . . ? C13 C14 C9 120.41(14) . . ? C13 C14 H14 119.8 . . ? C9 C14 H14 119.8 . . ? C16 C15 C20 118.96(13) . . ? C16 C15 C7 122.75(13) . . ? C20 C15 C7 118.27(13) . . ? C17 C16 C15 120.23(13) . . ? C17 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? C18 C17 C16 119.58(13) . . ? C18 C17 O2 120.95(13) . . ? C16 C17 O2 119.41(13) . . ? F1 C18 C17 118.40(13) . . ? F1 C18 C19 119.93(13) . . ? C17 C18 C19 121.67(14) . . ? C18 C19 C20 118.81(13) . . ? C18 C19 H19 120.6 . . ? C20 C19 H19 120.6 . . ? C19 C20 C15 120.74(13) . . ? C19 C20 H20 119.6 . . ? C15 C20 H20 119.6 . . ? C26 C21 C22 121.31(14) . . ? C26 C21 O2 123.51(13) . . ? C22 C21 O2 115.17(14) . . ? C21 C22 C23 119.05(16) . . ? C21 C22 H22 120.5 . . ? C23 C22 H22 120.5 . . ? C24 C23 C22 120.30(16) . . ? C24 C23 H23 119.9 . . ? C22 C23 H23 119.9 . . ? C25 C24 C23 119.85(16) . . ? C25 C24 H24 120.1 . . ? C23 C24 H24 120.1 . . ? C24 C25 C26 120.65(17) . . ? C24 C25 H25 119.7 . . ? C26 C25 H25 119.7 . . ? C21 C26 C25 118.83(15) . . ? C21 C26 H26 120.6 . . ? C25 C26 H26 120.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 N2 N4 C7 -0.15(16) . . . . ? C5 N2 N4 C7 177.57(12) . . . . ? C7 N3 N5 C8 -163.85(13) . . . . ? C6 N3 N5 C8 34.6(2) . . . . ? C4 O1 C1 C2 -58.37(18) . . . . ? C5 N1 C2 C1 170.00(13) . . . . ? C3 N1 C2 C1 -57.94(16) . . . . ? O1 C1 C2 N1 57.46(18) . . . . ? C5 N1 C3 C4 -169.66(13) . . . . ? C2 N1 C3 C4 58.85(16) . . . . ? C1 O1 C4 C3 59.87(17) . . . . ? N1 C3 C4 O1 -60.10(17) . . . . ? C2 N1 C5 N2 56.53(17) . . . . ? C3 N1 C5 N2 -72.83(16) . . . . ? C6 N2 C5 N1 -109.41(16) . . . . ? N4 N2 C5 N1 73.18(17) . . . . ? N4 N2 C6 N3 -0.47(15) . . . . ? C5 N2 C6 N3 -178.03(13) . . . . ? N4 N2 C6 S1 176.71(11) . . . . ? C5 N2 C6 S1 -0.8(2) . . . . ? C7 N3 C6 N2 0.87(15) . . . . ? N5 N3 C6 N2 164.07(13) . . . . ? C7 N3 C6 S1 -176.22(12) . . . . ? N5 N3 C6 S1 -13.0(2) . . . . ? N2 N4 C7 N3 0.72(15) . . . . ? N2 N4 C7 C15 179.64(12) . . . . ? C6 N3 C7 N4 -1.05(16) . . . . ? N5 N3 C7 N4 -166.14(12) . . . . ? C6 N3 C7 C15 -179.93(13) . . . . ? N5 N3 C7 C15 15.0(2) . . . . ? N3 N5 C8 C9 -179.49(12) . . . . ? N5 C8 C9 C14 -4.6(2) . . . . ? N5 C8 C9 C10 176.04(13) . . . . ? C14 C9 C10 C11 0.5(2) . . . . ? C8 C9 C10 C11 179.84(14) . . . . ? C9 C10 C11 C12 -0.6(2) . . . . ? C10 C11 C12 C13 0.0(2) . . . . ? C10 C11 C12 Cl1 179.73(11) . . . . ? C11 C12 C13 C14 0.7(2) . . . . ? Cl1 C12 C13 C14 -179.04(12) . . . . ? C12 C13 C14 C9 -0.8(2) . . . . ? C10 C9 C14 C13 0.2(2) . . . . ? C8 C9 C14 C13 -179.11(14) . . . . ? N4 C7 C15 C16 -162.62(14) . . . . ? N3 C7 C15 C16 16.1(2) . . . . ? N4 C7 C15 C20 16.0(2) . . . . ? N3 C7 C15 C20 -165.30(13) . . . . ? C20 C15 C16 C17 1.0(2) . . . . ? C7 C15 C16 C17 179.51(13) . . . . ? C15 C16 C17 C18 -1.4(2) . . . . ? C15 C16 C17 O2 -178.71(12) . . . . ? C21 O2 C17 C18 85.58(16) . . . . ? C21 O2 C17 C16 -97.16(15) . . . . ? C16 C17 C18 F1 -179.98(12) . . . . ? O2 C17 C18 F1 -2.7(2) . . . . ? C16 C17 C18 C19 0.8(2) . . . . ? O2 C17 C18 C19 178.10(13) . . . . ? F1 C18 C19 C20 -178.99(13) . . . . ? C17 C18 C19 C20 0.2(2) . . . . ? C18 C19 C20 C15 -0.6(2) . . . . ? C16 C15 C20 C19 0.1(2) . . . . ? C7 C15 C20 C19 -178.56(13) . . . . ? C17 O2 C21 C26 -13.58(19) . . . . ? C17 O2 C21 C22 167.52(13) . . . . ? C26 C21 C22 C23 0.2(2) . . . . ? O2 C21 C22 C23 179.14(13) . . . . ? C21 C22 C23 C24 -0.4(2) . . . . ? C22 C23 C24 C25 0.2(3) . . . . ? C23 C24 C25 C26 0.2(3) . . . . ? C22 C21 C26 C25 0.2(2) . . . . ? O2 C21 C26 C25 -178.64(14) . . . . ? C24 C25 C26 C21 -0.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.230 _refine_diff_density_min -0.377 _refine_diff_density_rms 0.058 _database_code_depnum_ccdc_archive 'CCDC 963712' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_TRZ-2FormII _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; C26 H23 Cl F N5 O2 S1, 0.5C7 H8 ; _chemical_formula_sum 'C29.50 H27 Cl F N5 O2 S' _chemical_formula_weight 570.07 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.5674(8) _cell_length_b 13.5041(17) _cell_length_c 16.236(2) _cell_angle_alpha 71.902(6) _cell_angle_beta 86.120(6) _cell_angle_gamma 89.592(6) _cell_volume 1365.4(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 780 _cell_measurement_theta_min 3.07 _cell_measurement_theta_max 23.30 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.387 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 594 _exptl_absorpt_coefficient_mu 0.261 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9306 _exptl_absorpt_correction_T_max 0.9794 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16778 _diffrn_reflns_av_R_equivalents 0.0460 _diffrn_reflns_av_sigmaI/netI 0.0411 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4784 _reflns_number_gt 4375 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0458P)^2^+1.0008P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4784 _refine_ls_number_parameters 361 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0462 _refine_ls_R_factor_gt 0.0427 _refine_ls_wR_factor_ref 0.1135 _refine_ls_wR_factor_gt 0.1108 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.068 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _iucr_refine_instruction_details ; TITL TRZ-2 II in P-1 CELL 0.71073 6.5674 13.5041 16.2358 71.902 86.120 89.592 ZERR 2.00 0.0008 0.0017 0.0020 0.006 0.006 0.006 LATT 1 SFAC C H N O F S CL UNIT 59 54 10 4 2 2 2 MERG 2 L.S. 12 EXYZ C29A C29B EADP C29A C29B BOND $H ACTA OMIT -1 50 DFIX 1.5 C29A C30 CONF SIZE 0.08 0.1 0.28 TEMP -173 FMAP 2 PLAN 5 WGHT 0.045800 1.000800 FVAR 0.15097 PART 1 C29A 1 0.041740 0.918032 0.473813 10.50000 0.14869 0.10892 = 0.05038 0.01886 -0.03688 -0.00402 C30 1 0.121315 0.848897 0.450052 10.50000 0.08604 0.13498 = 0.04108 0.01905 0.02155 0.07425 AFIX 33 H30A 2 0.264817 0.867232 0.431195 10.50000 -1.50000 H30B 2 0.050104 0.840256 0.401540 10.50000 -1.50000 H30C 2 0.113060 0.783570 0.498299 10.50000 -1.50000 AFIX 0 PART 2 C29B 1 0.041740 0.918032 0.473813 10.50000 0.14869 0.10892 = 0.05038 0.01886 -0.03688 -0.00402 AFIX 43 H29B 2 0.062948 0.857558 0.456413 10.50000 -1.20000 AFIX 0 PART 0 C28 1 0.217437 0.991168 0.464473 11.00000 0.19429 0.09161 = 0.07657 -0.00474 -0.03274 -0.05368 AFIX 43 H28 2 0.352092 0.984333 0.441751 11.00000 -1.20000 AFIX 0 C27 1 0.151888 1.065141 0.493018 11.00000 0.07777 0.10798 = 0.05605 0.00374 -0.00949 -0.02578 AFIX 43 H27 2 0.251552 1.116563 0.491184 11.00000 -1.20000 AFIX 0 S1 6 0.375159 0.107944 0.686257 11.00000 0.04020 0.03540 = 0.04391 -0.02237 -0.01722 0.00710 CL1 7 -0.380239 0.660883 0.533376 11.00000 0.04276 0.03573 = 0.05232 -0.00964 -0.02106 0.01283 F1 5 0.775466 0.597351 0.941053 11.00000 0.03189 0.03078 = 0.04160 -0.01956 -0.00343 -0.00333 O2 4 0.396543 0.567209 0.897984 11.00000 0.02664 0.02537 = 0.02622 -0.00725 0.00126 0.00549 N3 3 0.491882 0.259471 0.757482 11.00000 0.02314 0.02146 = 0.02349 -0.00652 -0.00394 0.00279 O1 4 0.609882 -0.167872 1.038734 11.00000 0.04101 0.03364 = 0.02681 -0.00608 -0.00365 -0.00661 N2 3 0.688344 0.127396 0.780809 11.00000 0.02565 0.02082 = 0.02627 -0.00810 -0.00357 0.00232 N4 3 0.771688 0.192602 0.820561 11.00000 0.02420 0.02198 = 0.02411 -0.00750 -0.00235 0.00075 N5 3 0.363495 0.342328 0.722080 11.00000 0.02668 0.02606 = 0.02489 -0.00777 -0.00676 0.00639 N1 3 0.744035 -0.056454 0.864965 11.00000 0.02466 0.02260 = 0.02587 -0.00736 -0.00332 0.00199 C17 1 0.555196 0.505580 0.882512 11.00000 0.02243 0.02275 = 0.02048 -0.00449 -0.00002 0.00254 C15 1 0.679889 0.360824 0.837928 11.00000 0.02416 0.02100 = 0.01883 -0.00384 -0.00159 0.00030 C20 1 0.873651 0.377685 0.862160 11.00000 0.02157 0.02370 = 0.02367 -0.00403 -0.00223 0.00293 AFIX 43 H20 2 0.983029 0.334212 0.854603 11.00000 -1.20000 AFIX 0 C14 1 0.093706 0.511115 0.655019 11.00000 0.02783 0.03134 = 0.02714 -0.00928 -0.00704 -0.00040 AFIX 43 H14 2 0.210058 0.527344 0.680381 11.00000 -1.20000 AFIX 0 C11 1 -0.245009 0.464184 0.579466 11.00000 0.02469 0.03588 = 0.02840 -0.00776 -0.00685 -0.00127 AFIX 43 H11 2 -0.360631 0.448634 0.553300 11.00000 -1.20000 AFIX 0 C3 1 0.849523 -0.046300 0.938362 11.00000 0.02737 0.02753 = 0.03120 -0.00774 -0.00813 0.00006 AFIX 23 H3A 2 0.793110 0.012665 0.956222 11.00000 -1.20000 H3B 2 0.996710 -0.032327 0.921403 11.00000 -1.20000 AFIX 0 C7 1 0.650371 0.272341 0.805333 11.00000 0.01925 0.02371 = 0.02080 -0.00504 -0.00096 -0.00009 C21 1 0.348817 0.655501 0.830806 11.00000 0.02720 0.02142 = 0.02944 -0.01021 -0.00540 0.00098 C19 1 0.908037 0.456974 0.897035 11.00000 0.02094 0.02893 = 0.02836 -0.00689 -0.00422 -0.00189 AFIX 43 H19 2 1.039481 0.467832 0.914070 11.00000 -1.20000 AFIX 0 C9 1 0.062619 0.409672 0.653650 11.00000 0.02297 0.02874 = 0.02086 -0.00509 -0.00137 0.00073 C10 1 -0.108655 0.387390 0.616026 11.00000 0.02898 0.02727 = 0.03112 -0.00820 -0.00489 -0.00146 AFIX 43 H10 2 -0.131992 0.318241 0.615519 11.00000 -1.20000 AFIX 0 C12 1 -0.210242 0.563748 0.581647 11.00000 0.02792 0.03215 = 0.02396 -0.00413 -0.00402 0.00538 C13 1 -0.043523 0.588368 0.619740 11.00000 0.03577 0.02710 = 0.03369 -0.00923 -0.00647 0.00142 AFIX 43 H13 2 -0.023663 0.657225 0.621624 11.00000 -1.20000 AFIX 0 C6 1 0.515476 0.164313 0.741471 11.00000 0.02722 0.02380 = 0.02465 -0.00661 -0.00170 0.00201 C1 1 0.505133 -0.178383 0.967402 11.00000 0.03424 0.03162 = 0.03395 -0.00916 -0.00474 -0.00640 AFIX 23 H1A 2 0.358621 -0.192917 0.985646 11.00000 -1.20000 H1B 2 0.560909 -0.238234 0.950660 11.00000 -1.20000 AFIX 0 C16 1 0.520199 0.425455 0.849236 11.00000 0.02030 0.02636 = 0.02187 -0.00573 -0.00301 0.00002 AFIX 43 H16 2 0.387251 0.414092 0.833939 11.00000 -1.20000 AFIX 0 C8 1 0.198802 0.323885 0.692070 11.00000 0.02716 0.02616 = 0.03051 -0.00766 -0.00319 0.00053 AFIX 43 H8 2 0.164401 0.254744 0.694592 11.00000 -1.20000 AFIX 0 C18 1 0.747584 0.519950 0.906572 11.00000 0.02913 0.02119 = 0.02391 -0.00755 -0.00111 -0.00248 C5 1 0.783805 0.026097 0.785337 11.00000 0.02818 0.02288 = 0.02739 -0.00926 -0.00019 0.00479 AFIX 23 H5A 2 0.736273 0.003198 0.737485 11.00000 -1.20000 H5B 2 0.933372 0.037309 0.774917 11.00000 -1.20000 AFIX 0 C22 1 0.180698 0.708687 0.849354 11.00000 0.02718 0.02721 = 0.04395 -0.01455 -0.00021 -0.00027 AFIX 43 H22 2 0.110430 0.685703 0.905220 11.00000 -1.20000 AFIX 0 C2 1 0.526774 -0.080977 0.889801 11.00000 0.02556 0.02945 = 0.02942 -0.00881 -0.00421 -0.00106 AFIX 23 H2A 2 0.459153 -0.091921 0.840578 11.00000 -1.20000 H2B 2 0.459977 -0.022076 0.904450 11.00000 -1.20000 AFIX 0 C4 1 0.821009 -0.146483 1.013013 11.00000 0.03716 0.02936 = 0.03405 -0.00630 -0.01146 0.00034 AFIX 23 H4A 2 0.881005 -0.204783 0.995214 11.00000 -1.20000 H4B 2 0.893409 -0.140660 1.062885 11.00000 -1.20000 AFIX 0 C24 1 0.218414 0.829942 0.706557 11.00000 0.07827 0.03135 = 0.04629 -0.00790 -0.01576 0.02303 AFIX 43 H24 2 0.174150 0.889911 0.663430 11.00000 -1.20000 AFIX 0 C23 1 0.114547 0.795525 0.786512 11.00000 0.03984 0.02917 = 0.05922 -0.01804 -0.01079 0.01113 AFIX 43 H23 2 -0.002951 0.831294 0.798820 11.00000 -1.20000 AFIX 0 C25 1 0.387034 0.777097 0.689209 11.00000 0.09311 0.04264 = 0.03669 0.00156 0.01316 0.02267 AFIX 43 H25 2 0.458674 0.801163 0.633681 11.00000 -1.20000 AFIX 0 C26 1 0.455381 0.688894 0.751315 11.00000 0.05667 0.03535 = 0.03772 -0.00505 0.00985 0.01734 AFIX 43 H26 2 0.572507 0.652950 0.738891 11.00000 -1.20000 HKLF 4 REM TRY1 in P-1 REM R1 = 0.0427 for 4375 Fo > 4sig(Fo) and 0.0462 for all 4784 data REM 361 parameters refined using 1 restraints END WGHT 0.0457 1.0028 REM Highest difference peak 0.777, deepest hole -0.413, 1-sigma level 0.051 Q1 1 0.1822 0.9014 0.4608 11.00000 0.05 0.78 Q2 1 -0.0567 0.8829 0.4834 11.00000 0.05 0.56 Q3 1 0.0711 0.8394 0.4458 11.00000 0.05 0.49 Q4 1 0.0293 0.9523 0.4883 11.00000 0.05 0.48 Q5 1 0.2412 0.8423 0.4263 11.00000 0.05 0.26 ; 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 C29A C 0.0417(10) 0.9180(4) 0.4738(3) 0.1112(17) Uani 0.50 1 d PD . 1 C30 C 0.1213(12) 0.8489(7) 0.4501(4) 0.100(3) Uani 0.50 1 d PD A 1 H30A H 0.2648 0.8672 0.4312 0.149 Uiso 0.50 1 calc PR A 1 H30B H 0.0501 0.8403 0.4015 0.149 Uiso 0.50 1 calc PR A 1 H30C H 0.1131 0.7836 0.4983 0.149 Uiso 0.50 1 calc PR A 1 C29B C 0.0417(10) 0.9180(4) 0.4738(3) 0.1112(17) Uani 0.50 1 d P . 2 H29B H 0.0629 0.8576 0.4564 0.133 Uiso 0.50 1 calc PR . 2 C28 C 0.2174(11) 0.9912(4) 0.4645(3) 0.124(2) Uani 1 1 d . . . H28 H 0.3521 0.9843 0.4418 0.149 Uiso 1 1 calc R . 1 C27 C 0.1519(6) 1.0651(4) 0.4930(2) 0.0869(12) Uani 1 1 d . . . H27 H 0.2516 1.1166 0.4912 0.104 Uiso 1 1 calc R . . S1 S 0.37516(9) 0.10794(4) 0.68626(4) 0.03687(16) Uani 1 1 d . . . Cl1 Cl -0.38024(9) 0.66088(4) 0.53338(4) 0.04374(17) Uani 1 1 d . . . F1 F 0.77547(17) 0.59735(9) 0.94105(8) 0.0328(3) Uani 1 1 d . . . O2 O 0.3965(2) 0.56721(10) 0.89798(8) 0.0264(3) Uani 1 1 d . . . N3 N 0.4919(2) 0.25947(12) 0.75748(10) 0.0227(3) Uani 1 1 d . . . O1 O 0.6099(2) -0.16787(11) 1.03873(9) 0.0345(3) Uani 1 1 d . . . N2 N 0.6883(2) 0.12740(12) 0.78081(10) 0.0240(3) Uani 1 1 d . . . N4 N 0.7717(2) 0.19260(12) 0.82056(10) 0.0233(3) Uani 1 1 d . . . N5 N 0.3635(2) 0.34233(12) 0.72208(10) 0.0257(4) Uani 1 1 d . . . N1 N 0.7440(2) -0.05645(12) 0.86497(10) 0.0244(3) Uani 1 1 d . . . C17 C 0.5552(3) 0.50558(14) 0.88251(11) 0.0225(4) Uani 1 1 d . . . C15 C 0.6799(3) 0.36082(14) 0.83793(11) 0.0219(4) Uani 1 1 d . . . C20 C 0.8737(3) 0.37768(15) 0.86216(12) 0.0237(4) Uani 1 1 d . . . H20 H 0.9830 0.3342 0.8546 0.028 Uiso 1 1 calc R . . C14 C 0.0937(3) 0.51112(16) 0.65502(13) 0.0285(4) Uani 1 1 d . . . H14 H 0.2101 0.5273 0.6804 0.034 Uiso 1 1 calc R . . C11 C -0.2450(3) 0.46418(16) 0.57947(13) 0.0299(4) Uani 1 1 d . . . H11 H -0.3606 0.4486 0.5533 0.036 Uiso 1 1 calc R . . C3 C 0.8495(3) -0.04630(15) 0.93836(13) 0.0287(4) Uani 1 1 d . . . H3A H 0.7931 0.0127 0.9562 0.034 Uiso 1 1 calc R . . H3B H 0.9967 -0.0323 0.9214 0.034 Uiso 1 1 calc R . . C7 C 0.6504(3) 0.27234(14) 0.80533(11) 0.0217(4) Uani 1 1 d . . . C21 C 0.3488(3) 0.65550(14) 0.83081(12) 0.0253(4) Uani 1 1 d . . . C19 C 0.9080(3) 0.45697(15) 0.89703(12) 0.0264(4) Uani 1 1 d . . . H19 H 1.0395 0.4678 0.9141 0.032 Uiso 1 1 calc R . . C9 C 0.0626(3) 0.40967(15) 0.65365(12) 0.0248(4) Uani 1 1 d . . . C10 C -0.1087(3) 0.38739(16) 0.61603(13) 0.0292(4) Uani 1 1 d . . . H10 H -0.1320 0.3182 0.6155 0.035 Uiso 1 1 calc R . . C12 C -0.2102(3) 0.56375(16) 0.58165(12) 0.0290(4) Uani 1 1 d . . . C13 C -0.0435(3) 0.58837(16) 0.61974(13) 0.0320(5) Uani 1 1 d . . . H13 H -0.0237 0.6572 0.6216 0.038 Uiso 1 1 calc R . . C6 C 0.5155(3) 0.16431(15) 0.74147(12) 0.0254(4) Uani 1 1 d . . . C1 C 0.5051(3) -0.17838(17) 0.96740(14) 0.0334(5) Uani 1 1 d . . . H1A H 0.3586 -0.1929 0.9856 0.040 Uiso 1 1 calc R . . H1B H 0.5609 -0.2382 0.9507 0.040 Uiso 1 1 calc R . . C16 C 0.5202(3) 0.42545(15) 0.84924(12) 0.0232(4) Uani 1 1 d . . . H16 H 0.3873 0.4141 0.8339 0.028 Uiso 1 1 calc R . . C8 C 0.1988(3) 0.32389(16) 0.69207(13) 0.0282(4) Uani 1 1 d . . . H8 H 0.1644 0.2547 0.6946 0.034 Uiso 1 1 calc R . . C18 C 0.7476(3) 0.51995(14) 0.90657(12) 0.0246(4) Uani 1 1 d . . . C5 C 0.7838(3) 0.02610(14) 0.78534(12) 0.0259(4) Uani 1 1 d . . . H5A H 0.7363 0.0032 0.7375 0.031 Uiso 1 1 calc R . . H5B H 0.9334 0.0373 0.7749 0.031 Uiso 1 1 calc R . . C22 C 0.1807(3) 0.70869(16) 0.84935(15) 0.0321(5) Uani 1 1 d . . . H22 H 0.1104 0.6857 0.9052 0.038 Uiso 1 1 calc R . . C2 C 0.5268(3) -0.08098(16) 0.88980(13) 0.0281(4) Uani 1 1 d . . . H2A H 0.4592 -0.0919 0.8406 0.034 Uiso 1 1 calc R . . H2B H 0.4600 -0.0221 0.9044 0.034 Uiso 1 1 calc R . . C4 C 0.8210(3) -0.14648(16) 1.01301(14) 0.0339(5) Uani 1 1 d . . . H4A H 0.8810 -0.2048 0.9952 0.041 Uiso 1 1 calc R . . H4B H 0.8934 -0.1407 1.0629 0.041 Uiso 1 1 calc R . . C24 C 0.2184(5) 0.82994(19) 0.70656(17) 0.0525(7) Uani 1 1 d . . . H24 H 0.1742 0.8899 0.6634 0.063 Uiso 1 1 calc R . . C23 C 0.1145(4) 0.79552(17) 0.78651(16) 0.0415(6) Uani 1 1 d . . . H23 H -0.0030 0.8313 0.7988 0.050 Uiso 1 1 calc R . . C25 C 0.3870(5) 0.7771(2) 0.68921(17) 0.0616(8) Uani 1 1 d . . . H25 H 0.4587 0.8012 0.6337 0.074 Uiso 1 1 calc R . . C26 C 0.4554(4) 0.68889(18) 0.75132(15) 0.0454(6) Uani 1 1 d . . . H26 H 0.5725 0.6529 0.7389 0.054 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 C29A 0.149(5) 0.109(4) 0.050(2) 0.019(2) -0.037(3) -0.004(3) C30 0.086(5) 0.135(7) 0.041(3) 0.019(4) 0.022(3) 0.074(5) C29B 0.149(5) 0.109(4) 0.050(2) 0.019(2) -0.037(3) -0.004(3) C28 0.194(6) 0.092(3) 0.077(3) -0.005(3) -0.033(3) -0.054(4) C27 0.078(3) 0.108(3) 0.056(2) 0.004(2) -0.0095(18) -0.026(2) S1 0.0402(3) 0.0354(3) 0.0439(3) -0.0224(3) -0.0172(2) 0.0071(2) Cl1 0.0428(3) 0.0357(3) 0.0523(4) -0.0096(3) -0.0211(3) 0.0128(2) F1 0.0319(6) 0.0308(6) 0.0416(7) -0.0196(5) -0.0034(5) -0.0033(5) O2 0.0266(7) 0.0254(7) 0.0262(7) -0.0073(6) 0.0013(5) 0.0055(5) N3 0.0231(8) 0.0215(8) 0.0235(8) -0.0065(6) -0.0039(6) 0.0028(6) O1 0.0410(8) 0.0336(8) 0.0268(7) -0.0061(6) -0.0036(6) -0.0066(6) N2 0.0257(8) 0.0208(8) 0.0263(8) -0.0081(6) -0.0036(6) 0.0023(6) N4 0.0242(8) 0.0220(8) 0.0241(8) -0.0075(6) -0.0024(6) 0.0007(6) N5 0.0267(8) 0.0261(8) 0.0249(8) -0.0078(7) -0.0068(7) 0.0064(7) N1 0.0247(8) 0.0226(8) 0.0259(8) -0.0074(7) -0.0033(6) 0.0020(6) C17 0.0224(9) 0.0228(9) 0.0205(9) -0.0045(7) 0.0000(7) 0.0025(7) C15 0.0242(9) 0.0210(9) 0.0188(9) -0.0038(7) -0.0016(7) 0.0003(7) C20 0.0216(9) 0.0237(9) 0.0237(9) -0.0040(8) -0.0022(7) 0.0029(7) C14 0.0278(10) 0.0313(11) 0.0271(10) -0.0093(8) -0.0070(8) -0.0004(8) C11 0.0247(10) 0.0359(11) 0.0284(10) -0.0078(9) -0.0069(8) -0.0013(8) C3 0.0274(10) 0.0275(10) 0.0312(11) -0.0077(8) -0.0081(8) 0.0001(8) C7 0.0192(9) 0.0237(9) 0.0208(9) -0.0050(7) -0.0010(7) -0.0001(7) C21 0.0272(10) 0.0214(9) 0.0294(10) -0.0102(8) -0.0054(8) 0.0010(8) C19 0.0209(9) 0.0289(10) 0.0284(10) -0.0069(8) -0.0042(7) -0.0019(8) C9 0.0230(9) 0.0287(10) 0.0209(9) -0.0051(8) -0.0014(7) 0.0007(8) C10 0.0290(10) 0.0273(10) 0.0311(11) -0.0082(8) -0.0049(8) -0.0015(8) C12 0.0279(10) 0.0321(11) 0.0240(10) -0.0041(8) -0.0040(8) 0.0054(8) C13 0.0358(11) 0.0271(11) 0.0337(11) -0.0092(9) -0.0065(9) 0.0014(9) C6 0.0272(10) 0.0238(10) 0.0247(10) -0.0066(8) -0.0017(8) 0.0020(8) C1 0.0342(11) 0.0316(11) 0.0340(11) -0.0092(9) -0.0047(9) -0.0064(9) C16 0.0203(9) 0.0264(10) 0.0219(9) -0.0057(8) -0.0030(7) 0.0000(7) C8 0.0272(10) 0.0262(10) 0.0305(10) -0.0077(8) -0.0032(8) 0.0005(8) C18 0.0291(10) 0.0212(9) 0.0239(9) -0.0076(8) -0.0011(8) -0.0025(8) C5 0.0282(10) 0.0229(10) 0.0274(10) -0.0093(8) -0.0002(8) 0.0048(8) C22 0.0272(10) 0.0272(10) 0.0439(12) -0.0145(9) -0.0002(9) -0.0003(8) C2 0.0256(10) 0.0294(11) 0.0294(10) -0.0088(8) -0.0042(8) -0.0011(8) C4 0.0372(12) 0.0294(11) 0.0340(11) -0.0063(9) -0.0115(9) 0.0003(9) C24 0.0783(19) 0.0313(13) 0.0463(15) -0.0079(11) -0.0158(13) 0.0230(12) C23 0.0398(13) 0.0292(11) 0.0592(15) -0.0180(11) -0.0108(11) 0.0111(10) C25 0.093(2) 0.0426(15) 0.0367(14) 0.0016(11) 0.0132(14) 0.0227(14) C26 0.0567(15) 0.0353(13) 0.0377(13) -0.0050(10) 0.0099(11) 0.0173(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C29A C30 1.218(8) . ? C29A C27 1.392(7) 2_576 ? C29A C28 1.493(7) . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C28 C27 1.285(7) . ? C28 H28 0.9500 . ? C27 C29B 1.392(7) 2_576 ? C27 C29A 1.392(7) 2_576 ? C27 H27 0.9500 . ? S1 C6 1.667(2) . ? Cl1 C12 1.744(2) . ? F1 C18 1.349(2) . ? O2 C17 1.387(2) . ? O2 C21 1.394(2) . ? N3 C7 1.383(2) . ? N3 C6 1.394(2) . ? N3 N5 1.395(2) . ? O1 C4 1.426(3) . ? O1 C1 1.430(2) . ? N2 C6 1.356(2) . ? N2 N4 1.378(2) . ? N2 C5 1.484(2) . ? N4 C7 1.306(2) . ? N5 C8 1.273(3) . ? N1 C5 1.430(2) . ? N1 C3 1.461(2) . ? N1 C2 1.468(2) . ? C17 C16 1.378(3) . ? C17 C18 1.380(3) . ? C15 C20 1.398(3) . ? C15 C16 1.398(3) . ? C15 C7 1.468(3) . ? C20 C19 1.384(3) . ? C20 H20 0.9500 . ? C14 C13 1.383(3) . ? C14 C9 1.394(3) . ? C14 H14 0.9500 . ? C11 C12 1.377(3) . ? C11 C10 1.381(3) . ? C11 H11 0.9500 . ? C3 C4 1.513(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C21 C26 1.371(3) . ? C21 C22 1.380(3) . ? C19 C18 1.380(3) . ? C19 H19 0.9500 . ? C9 C10 1.393(3) . ? C9 C8 1.464(3) . ? C10 H10 0.9500 . ? C12 C13 1.384(3) . ? C13 H13 0.9500 . ? C1 C2 1.512(3) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C16 H16 0.9500 . ? C8 H8 0.9500 . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C22 C23 1.384(3) . ? C22 H22 0.9500 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C24 C23 1.370(4) . ? C24 C25 1.373(4) . ? C24 H24 0.9500 . ? C23 H23 0.9500 . ? C25 C26 1.394(3) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? 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 C30 C29A C27 135.4(7) . 2_576 ? C30 C29A C28 101.9(8) . . ? C27 C29A C28 122.7(5) 2_576 . ? C29A C30 H30A 109.5 . . ? C29A C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C29A C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C27 C28 C29A 107.0(6) . . ? C27 C28 H28 126.5 . . ? C29A C28 H28 126.5 . . ? C28 C27 C29B 130.3(5) . 2_576 ? C28 C27 C29A 130.3(5) . 2_576 ? C28 C27 H27 114.8 . . ? C29B C27 H27 114.8 2_576 . ? C29A C27 H27 114.8 2_576 . ? C17 O2 C21 118.31(14) . . ? C7 N3 C6 108.38(15) . . ? C7 N3 N5 120.12(15) . . ? C6 N3 N5 130.49(15) . . ? C4 O1 C1 109.74(15) . . ? C6 N2 N4 113.60(15) . . ? C6 N2 C5 125.83(16) . . ? N4 N2 C5 120.55(15) . . ? C7 N4 N2 104.68(15) . . ? C8 N5 N3 118.65(16) . . ? C5 N1 C3 115.01(15) . . ? C5 N1 C2 114.50(15) . . ? C3 N1 C2 110.71(15) . . ? C16 C17 C18 119.54(17) . . ? C16 C17 O2 120.85(17) . . ? C18 C17 O2 119.44(16) . . ? C20 C15 C16 119.08(17) . . ? C20 C15 C7 118.28(16) . . ? C16 C15 C7 122.58(17) . . ? C19 C20 C15 120.77(17) . . ? C19 C20 H20 119.6 . . ? C15 C20 H20 119.6 . . ? C13 C14 C9 120.53(18) . . ? C13 C14 H14 119.7 . . ? C9 C14 H14 119.7 . . ? C12 C11 C10 118.74(18) . . ? C12 C11 H11 120.6 . . ? C10 C11 H11 120.6 . . ? N1 C3 C4 108.87(16) . . ? N1 C3 H3A 109.9 . . ? C4 C3 H3A 109.9 . . ? N1 C3 H3B 109.9 . . ? C4 C3 H3B 109.9 . . ? H3A C3 H3B 108.3 . . ? N4 C7 N3 110.76(16) . . ? N4 C7 C15 123.20(16) . . ? N3 C7 C15 126.02(16) . . ? C26 C21 C22 120.94(19) . . ? C26 C21 O2 124.27(18) . . ? C22 C21 O2 114.79(17) . . ? C18 C19 C20 118.68(17) . . ? C18 C19 H19 120.7 . . ? C20 C19 H19 120.7 . . ? C10 C9 C14 118.92(18) . . ? C10 C9 C8 117.89(18) . . ? C14 C9 C8 123.17(18) . . ? C11 C10 C9 121.06(19) . . ? C11 C10 H10 119.5 . . ? C9 C10 H10 119.5 . . ? C11 C12 C13 121.78(18) . . ? C11 C12 Cl1 118.48(15) . . ? C13 C12 Cl1 119.73(16) . . ? C14 C13 C12 118.95(19) . . ? C14 C13 H13 120.5 . . ? C12 C13 H13 120.5 . . ? N2 C6 N3 102.58(16) . . ? N2 C6 S1 127.11(15) . . ? N3 C6 S1 130.29(15) . . ? O1 C1 C2 111.65(16) . . ? O1 C1 H1A 109.3 . . ? C2 C1 H1A 109.3 . . ? O1 C1 H1B 109.3 . . ? C2 C1 H1B 109.3 . . ? H1A C1 H1B 108.0 . . ? C17 C16 C15 120.17(17) . . ? C17 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? N5 C8 C9 119.71(18) . . ? N5 C8 H8 120.1 . . ? C9 C8 H8 120.1 . . ? F1 C18 C17 118.07(16) . . ? F1 C18 C19 120.19(17) . . ? C17 C18 C19 121.74(17) . . ? N1 C5 N2 116.07(15) . . ? N1 C5 H5A 108.3 . . ? N2 C5 H5A 108.3 . . ? N1 C5 H5B 108.3 . . ? N2 C5 H5B 108.3 . . ? H5A C5 H5B 107.4 . . ? C21 C22 C23 119.9(2) . . ? C21 C22 H22 120.0 . . ? C23 C22 H22 120.0 . . ? N1 C2 C1 109.48(16) . . ? N1 C2 H2A 109.8 . . ? C1 C2 H2A 109.8 . . ? N1 C2 H2B 109.8 . . ? C1 C2 H2B 109.8 . . ? H2A C2 H2B 108.2 . . ? O1 C4 C3 110.83(17) . . ? O1 C4 H4A 109.5 . . ? C3 C4 H4A 109.5 . . ? O1 C4 H4B 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 108.1 . . ? C23 C24 C25 119.5(2) . . ? C23 C24 H24 120.3 . . ? C25 C24 H24 120.3 . . ? C24 C23 C22 120.0(2) . . ? C24 C23 H23 120.0 . . ? C22 C23 H23 120.0 . . ? C24 C25 C26 121.4(2) . . ? C24 C25 H25 119.3 . . ? C26 C25 H25 119.3 . . ? C21 C26 C25 118.1(2) . . ? C21 C26 H26 120.9 . . ? C25 C26 H26 120.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C30 C29A C28 C27 -176.3(5) . . . . ? C27 C29A C28 C27 0.8(6) 2_576 . . . ? C29A C28 C27 C29B -0.9(7) . . . 2_576 ? C29A C28 C27 C29A -0.9(7) . . . 2_576 ? C6 N2 N4 C7 -0.6(2) . . . . ? C5 N2 N4 C7 -179.00(16) . . . . ? C7 N3 N5 C8 -167.56(17) . . . . ? C6 N3 N5 C8 25.4(3) . . . . ? C21 O2 C17 C16 -88.7(2) . . . . ? C21 O2 C17 C18 96.0(2) . . . . ? C16 C15 C20 C19 0.1(3) . . . . ? C7 C15 C20 C19 -177.03(17) . . . . ? C5 N1 C3 C4 -170.77(16) . . . . ? C2 N1 C3 C4 57.5(2) . . . . ? N2 N4 C7 N3 0.3(2) . . . . ? N2 N4 C7 C15 178.64(16) . . . . ? C6 N3 C7 N4 0.0(2) . . . . ? N5 N3 C7 N4 -169.63(15) . . . . ? C6 N3 C7 C15 -178.24(17) . . . . ? N5 N3 C7 C15 12.1(3) . . . . ? C20 C15 C7 N4 20.5(3) . . . . ? C16 C15 C7 N4 -156.51(18) . . . . ? C20 C15 C7 N3 -161.42(17) . . . . ? C16 C15 C7 N3 21.6(3) . . . . ? C17 O2 C21 C26 -3.6(3) . . . . ? C17 O2 C21 C22 175.80(17) . . . . ? C15 C20 C19 C18 -0.7(3) . . . . ? C13 C14 C9 C10 0.1(3) . . . . ? C13 C14 C9 C8 -178.18(19) . . . . ? C12 C11 C10 C9 -0.8(3) . . . . ? C14 C9 C10 C11 0.8(3) . . . . ? C8 C9 C10 C11 179.24(18) . . . . ? C10 C11 C12 C13 -0.3(3) . . . . ? C10 C11 C12 Cl1 178.70(15) . . . . ? C9 C14 C13 C12 -1.2(3) . . . . ? C11 C12 C13 C14 1.3(3) . . . . ? Cl1 C12 C13 C14 -177.74(16) . . . . ? N4 N2 C6 N3 0.6(2) . . . . ? C5 N2 C6 N3 178.90(16) . . . . ? N4 N2 C6 S1 179.18(14) . . . . ? C5 N2 C6 S1 -2.5(3) . . . . ? C7 N3 C6 N2 -0.4(2) . . . . ? N5 N3 C6 N2 167.86(17) . . . . ? C7 N3 C6 S1 -178.90(15) . . . . ? N5 N3 C6 S1 -10.7(3) . . . . ? C4 O1 C1 C2 -58.7(2) . . . . ? C18 C17 C16 C15 -1.6(3) . . . . ? O2 C17 C16 C15 -176.90(16) . . . . ? C20 C15 C16 C17 1.1(3) . . . . ? C7 C15 C16 C17 178.06(17) . . . . ? N3 N5 C8 C9 -179.29(16) . . . . ? C10 C9 C8 N5 175.53(18) . . . . ? C14 C9 C8 N5 -6.1(3) . . . . ? C16 C17 C18 F1 -178.27(16) . . . . ? O2 C17 C18 F1 -2.9(3) . . . . ? C16 C17 C18 C19 1.0(3) . . . . ? O2 C17 C18 C19 176.37(17) . . . . ? C20 C19 C18 F1 179.41(17) . . . . ? C20 C19 C18 C17 0.2(3) . . . . ? C3 N1 C5 N2 -72.7(2) . . . . ? C2 N1 C5 N2 57.2(2) . . . . ? C6 N2 C5 N1 -100.0(2) . . . . ? N4 N2 C5 N1 78.2(2) . . . . ? C26 C21 C22 C23 1.6(3) . . . . ? O2 C21 C22 C23 -177.74(18) . . . . ? C5 N1 C2 C1 172.07(16) . . . . ? C3 N1 C2 C1 -55.9(2) . . . . ? O1 C1 C2 N1 56.4(2) . . . . ? C1 O1 C4 C3 60.3(2) . . . . ? N1 C3 C4 O1 -59.8(2) . . . . ? C25 C24 C23 C22 0.6(4) . . . . ? C21 C22 C23 C24 -1.4(3) . . . . ? C23 C24 C25 C26 0.0(5) . . . . ? C22 C21 C26 C25 -1.1(4) . . . . ? O2 C21 C26 C25 178.2(2) . . . . ? C24 C25 C26 C21 0.3(5) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.777 _refine_diff_density_min -0.413 _refine_diff_density_rms 0.051 _database_code_depnum_ccdc_archive 'CCDC 963713'