# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2006 data_global #============================================================================== _journal_coden_Cambridge 182 # 1. SUBMISSION DETAILS _publ_contact_author_name 'Prof. Dr. Franc Meyer' _publ_contact_author_address ; Institut f\"ur Anorganische Chemie Georg August Universit\"at G\"ottingen Tammannstra\&se 4 D-37077 G\"ottingen Germany ; _publ_contact_author_email franc.meyer@chemie.uni-goettingen.de _publ_contact_author_fax 49(551)393063 _publ_contact_author_phone 49(551)393012 _publ_requested_journal 'Chemical Communications' _publ_requested_coeditor_name ? #============================================================================== # 3. TITLE AND AUTHOR LIST _publ_section_title ; A versatile building block for pyrazole-pyrrole hybrid macrocycles ; loop_ _publ_author_name _publ_author_address 'Katsiaouni, Stamatia' ; Institut f\"ur Anorganische Chemie Georg August Universit\"at G\"ottingen Tammannstra\&se 4 D-37077 G\"ottingen Germany ; 'Dechert, Sebastian' ; Institut f\"ur Anorganische Chemie Georg August Universit\"at G\"ottingen Tammannstra\&se 4 D-37077 G\"ottingen Germany ; 'Br\"uckner, Christian' ; University of Connecticut Department of Chemistry Storrs Connecticut 06269-3060 USA ; 'Meyer, Franc' ; Institut f\"ur Anorganische Chemie Georg August Universit\"at G\"ottingen Tammannstra\&se 4 D-37077 G\"ottingen Germany ; #============================================================================== data_4 _database_code_depnum_ccdc_archive 'CCDC 622593' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C29 H34 N6, 2(C2 H6 O)' _chemical_formula_sum 'C33 H46 N6 O2' _chemical_formula_weight 558.76 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 2/c 1' _symmetry_space_group_name_Hall '-P 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 19.8688(8) _cell_length_b 7.9486(5) _cell_length_c 21.8773(8) _cell_angle_alpha 90.00 _cell_angle_beta 111.266(3) _cell_angle_gamma 90.00 _cell_volume 3219.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 62808 _cell_measurement_theta_min 1.90 _cell_measurement_theta_max 24.88 _exptl_crystal_description block _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.153 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1208 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 133(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 'Stoe IPDS II' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 62808 _diffrn_reflns_av_R_equivalents 0.0979 _diffrn_reflns_av_sigmaI/netI 0.0434 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 24.88 _reflns_number_total 5588 _reflns_number_gt 3865 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'X-AREA (Stoe & Cie, 2002)' _computing_cell_refinement 'X-AREA (Stoe & Cie, 2002)' _computing_data_reduction 'X-AREA (Stoe & Cie, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0719P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5588 _refine_ls_number_parameters 416 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0825 _refine_ls_R_factor_gt 0.0506 _refine_ls_wR_factor_ref 0.1263 _refine_ls_wR_factor_gt 0.1142 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.09972(10) 0.8071(2) 0.35411(8) 0.0363(4) Uani 1 1 d . . . N2 N 0.13098(9) 0.8003(2) 0.30835(8) 0.0382(4) Uani 1 1 d . . . N3 N 0.31358(10) 0.5926(2) 0.36780(8) 0.0357(4) Uani 1 1 d . . . N4 N 0.34070(10) 0.2965(2) 0.44409(9) 0.0385(4) Uani 1 1 d . . . N5 N 0.27070(10) 0.3000(2) 0.52581(9) 0.0391(4) Uani 1 1 d . . . N6 N 0.19176(9) 0.6012(2) 0.51577(9) 0.0355(4) Uani 1 1 d . . . C1 C 0.21242(11) 0.8757(3) 0.40648(10) 0.0359(5) Uani 1 1 d . . . H1A H 0.2559 0.9067 0.4389 0.080 Uiso 1 1 calc R . . C2 C 0.19989(11) 0.8428(3) 0.34046(10) 0.0341(5) Uani 1 1 d . . . C3 C 0.14705(11) 0.8528(3) 0.41348(10) 0.0334(5) Uani 1 1 d . . . C4 C 0.25333(12) 0.8495(3) 0.30642(11) 0.0405(5) Uani 1 1 d . . . H4A H 0.2294 0.8148 0.2612 0.080 Uiso 1 1 calc R . . H4B H 0.2692 0.9649 0.3063 0.080 Uiso 1 1 calc R . . C5 C 0.31832(11) 0.7400(3) 0.33780(10) 0.0366(5) Uani 1 1 d . . . C6 C 0.39003(12) 0.7625(3) 0.34404(10) 0.0380(5) Uani 1 1 d . . . C7 C 0.42968(11) 0.6221(3) 0.37935(10) 0.0369(5) Uani 1 1 d . . . C8 C 0.38083(11) 0.5184(3) 0.39366(10) 0.0358(5) Uani 1 1 d . . . C9 C 0.41907(13) 0.9086(3) 0.31717(11) 0.0455(6) Uani 1 1 d . . . H9A H 0.4708 0.9165 0.3404 0.080 Uiso 1 1 calc R . . H9B H 0.3974 1.0120 0.3248 0.080 Uiso 1 1 calc R . . C10 C 0.40376(15) 0.8908(4) 0.24453(12) 0.0562(7) Uani 1 1 d . . . H10A H 0.4254 0.7890 0.2367 0.080 Uiso 1 1 calc R . . H10B H 0.4237 0.9854 0.2296 0.080 Uiso 1 1 calc R . . H10C H 0.3525 0.8867 0.2211 0.080 Uiso 1 1 calc R . . C11 C 0.50905(12) 0.5882(3) 0.39643(11) 0.0453(6) Uani 1 1 d . . . H11A H 0.5347 0.6945 0.4031 0.080 Uiso 1 1 calc R . . H11B H 0.5272 0.5259 0.4373 0.080 Uiso 1 1 calc R . . C12 C 0.52456(15) 0.4903(4) 0.34430(13) 0.0597(7) Uani 1 1 d . . . H12A H 0.5032 0.3806 0.3404 0.080 Uiso 1 1 calc R . . H12B H 0.5758 0.4795 0.3561 0.080 Uiso 1 1 calc R . . H12C H 0.5045 0.5484 0.3032 0.080 Uiso 1 1 calc R . . C13 C 0.39248(12) 0.3689(3) 0.43242(10) 0.0375(5) Uani 1 1 d . . . H13 H 0.4386 0.3230 0.4496 0.080 Uiso 1 1 calc R . . C14 C 0.35344(11) 0.1575(3) 0.48663(10) 0.0337(5) Uani 1 1 d . . . C15 C 0.39653(11) 0.0209(3) 0.48603(11) 0.0385(5) Uani 1 1 d . . . H15 H 0.4227 0.0210 0.4583 0.080 Uiso 1 1 calc R . . C16 C 0.40079(12) -0.1161(3) 0.52668(11) 0.0449(6) Uani 1 1 d . . . H16 H 0.4292 -0.2082 0.5256 0.080 Uiso 1 1 calc R . . C17 C 0.36297(12) -0.1162(3) 0.56885(11) 0.0440(5) Uani 1 1 d . . . H17 H 0.3659 -0.2087 0.5958 0.080 Uiso 1 1 calc R . . C18 C 0.32089(12) 0.0207(3) 0.57107(10) 0.0382(5) Uani 1 1 d . . . H18 H 0.2962 0.0208 0.6000 0.080 Uiso 1 1 calc R . . C19 C 0.31540(11) 0.1582(3) 0.53018(10) 0.0348(5) Uani 1 1 d . . . C20 C 0.26773(12) 0.3693(3) 0.57748(10) 0.0379(5) Uani 1 1 d . . . H20 H 0.2926 0.3205 0.6181 0.080 Uiso 1 1 calc R . . C21 C 0.22703(11) 0.5205(3) 0.57453(10) 0.0355(5) Uani 1 1 d . . . C22 C 0.22007(11) 0.6204(3) 0.62416(10) 0.0350(5) Uani 1 1 d . . . C23 C 0.17984(11) 0.7648(3) 0.59405(10) 0.0359(5) Uani 1 1 d . . . C24 C 0.16383(11) 0.7493(3) 0.52686(10) 0.0345(5) Uani 1 1 d . . . C25 C 0.25375(12) 0.5870(3) 0.69675(10) 0.0425(5) Uani 1 1 d . . . H25A H 0.2637 0.4676 0.7036 0.080 Uiso 1 1 calc R . . H25B H 0.2194 0.6166 0.7171 0.080 Uiso 1 1 calc R . . C26 C 0.32327(14) 0.6842(4) 0.73016(12) 0.0566(7) Uani 1 1 d . . . H26A H 0.3588 0.6493 0.7125 0.080 Uiso 1 1 calc R . . H26B H 0.3408 0.6622 0.7764 0.080 Uiso 1 1 calc R . . H26C H 0.3142 0.8024 0.7226 0.080 Uiso 1 1 calc R . . C27 C 0.15454(14) 0.9056(3) 0.62615(12) 0.0473(6) Uani 1 1 d . . . H27A H 0.1595 1.0112 0.6060 0.080 Uiso 1 1 calc R . . H27B H 0.1852 0.9108 0.6722 0.080 Uiso 1 1 calc R . . C28 C 0.07647(18) 0.8852(4) 0.62059(18) 0.0780(10) Uani 1 1 d . . . H28A H 0.0457 0.8817 0.5751 0.080 Uiso 1 1 calc R . . H28B H 0.0629 0.9785 0.6415 0.080 Uiso 1 1 calc R . . H28C H 0.0714 0.7824 0.6416 0.080 Uiso 1 1 calc R . . C29 C 0.12503(12) 0.8695(3) 0.47228(10) 0.0388(5) Uani 1 1 d . . . H29A H 0.1345 0.9837 0.4888 0.080 Uiso 1 1 calc R . . H29B H 0.0735 0.8500 0.4586 0.080 Uiso 1 1 calc R . . O1 O 0.19398(9) 0.4451(2) 0.39572(8) 0.0401(4) Uani 1 1 d . . . C30A C 0.1528(3) 0.3436(7) 0.3412(3) 0.0576(18) Uani 0.648(13) 1 d P A 1 H30A H 0.1808 0.2458 0.3386 0.080 Uiso 0.648(13) 1 calc PR A 1 H30B H 0.1417 0.4075 0.3010 0.080 Uiso 0.648(13) 1 calc PR A 1 C31A C 0.0861(4) 0.2899(9) 0.3483(4) 0.100(3) Uani 0.648(13) 1 d P A 1 H31A H 0.0966 0.2465 0.3917 0.080 Uiso 0.648(13) 1 calc PR A 1 H31B H 0.0638 0.2036 0.3167 0.080 Uiso 0.648(13) 1 calc PR A 1 H31C H 0.0539 0.3840 0.3412 0.080 Uiso 0.648(13) 1 calc PR A 1 C30B C 0.1299(5) 0.3458(12) 0.3710(6) 0.054(3) Uani 0.352(13) 1 d P A 2 H30C H 0.0883 0.4157 0.3665 0.080 Uiso 0.352(13) 1 calc PR A 2 H30D H 0.1320 0.2569 0.4020 0.080 Uiso 0.352(13) 1 calc PR A 2 C31B C 0.1212(9) 0.2710(17) 0.3070(6) 0.100(5) Uani 0.352(13) 1 d P A 2 H31D H 0.1137 0.3588 0.2750 0.080 Uiso 0.352(13) 1 calc PR A 2 H31E H 0.0803 0.1967 0.2935 0.080 Uiso 0.352(13) 1 calc PR A 2 H31F H 0.1639 0.2090 0.3106 0.080 Uiso 0.352(13) 1 calc PR A 2 O2 O 0.04538(8) 0.7242(2) 0.17961(8) 0.0460(4) Uani 1 1 d . . . C32 C 0.08515(14) 0.6227(3) 0.15158(12) 0.0521(6) Uani 1 1 d . . . H32A H 0.0925 0.5122 0.1718 0.080 Uiso 1 1 calc R . . H32B H 0.1322 0.6728 0.1600 0.080 Uiso 1 1 calc R . . C33 C 0.04597(15) 0.6057(4) 0.07930(12) 0.0634(8) Uani 1 1 d . . . H33A H -0.0015 0.5616 0.0709 0.080 Uiso 1 1 calc R . . H33B H 0.0720 0.5304 0.0616 0.080 Uiso 1 1 calc R . . H33C H 0.0422 0.7140 0.0589 0.080 Uiso 1 1 calc R . . H1N H 0.0514(15) 0.781(3) 0.3431(12) 0.050(7) Uiso 1 1 d . . . H1O H 0.2254(16) 0.384(4) 0.4204(14) 0.064(9) Uiso 1 1 d . . . H2 H 0.0725(16) 0.747(4) 0.2198(15) 0.063(8) Uiso 1 1 d . . . H3 H 0.2730(16) 0.548(4) 0.3725(13) 0.065(8) Uiso 1 1 d . . . H6 H 0.1894(13) 0.561(3) 0.4748(13) 0.049(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0289(10) 0.0450(11) 0.0325(9) 0.0009(8) 0.0080(8) 0.0000(8) N2 0.0347(10) 0.0466(11) 0.0322(9) 0.0020(8) 0.0106(8) 0.0022(8) N3 0.0354(10) 0.0391(10) 0.0345(9) 0.0024(8) 0.0148(8) -0.0006(8) N4 0.0400(10) 0.0373(10) 0.0385(10) 0.0037(8) 0.0146(8) 0.0021(8) N5 0.0401(10) 0.0370(10) 0.0423(10) 0.0008(8) 0.0172(8) 0.0031(8) N6 0.0385(10) 0.0380(10) 0.0294(9) -0.0033(8) 0.0118(8) 0.0037(8) C1 0.0342(11) 0.0373(11) 0.0319(11) -0.0019(9) 0.0070(9) -0.0015(9) C2 0.0316(11) 0.0354(11) 0.0323(11) 0.0038(9) 0.0082(9) 0.0019(9) C3 0.0333(11) 0.0337(11) 0.0311(10) -0.0003(9) 0.0092(8) 0.0028(9) C4 0.0381(12) 0.0472(13) 0.0364(11) 0.0072(10) 0.0137(9) 0.0032(10) C5 0.0375(12) 0.0423(12) 0.0310(11) 0.0015(9) 0.0139(9) 0.0003(10) C6 0.0382(12) 0.0449(13) 0.0312(11) -0.0004(9) 0.0129(9) -0.0029(10) C7 0.0353(11) 0.0446(13) 0.0301(10) -0.0025(9) 0.0110(9) 0.0004(10) C8 0.0329(11) 0.0432(12) 0.0311(11) -0.0007(9) 0.0114(9) 0.0006(10) C9 0.0417(13) 0.0531(15) 0.0418(13) 0.0060(11) 0.0153(10) -0.0011(11) C10 0.0649(17) 0.0596(16) 0.0510(15) 0.0104(12) 0.0292(13) 0.0119(13) C11 0.0394(12) 0.0506(14) 0.0430(13) 0.0020(11) 0.0116(10) -0.0025(10) C12 0.0554(16) 0.0747(19) 0.0542(16) 0.0114(14) 0.0262(13) 0.0184(14) C13 0.0374(12) 0.0416(12) 0.0333(11) -0.0001(10) 0.0128(9) 0.0016(10) C14 0.0321(11) 0.0348(11) 0.0313(11) -0.0006(9) 0.0079(8) -0.0006(9) C15 0.0339(11) 0.0394(12) 0.0403(12) -0.0020(10) 0.0113(9) 0.0005(10) C16 0.0394(12) 0.0409(13) 0.0501(13) 0.0008(11) 0.0111(11) 0.0063(10) C17 0.0474(13) 0.0373(12) 0.0417(12) 0.0077(10) 0.0096(10) 0.0041(10) C18 0.0406(12) 0.0392(12) 0.0314(11) 0.0010(9) 0.0090(9) -0.0013(10) C19 0.0318(11) 0.0358(11) 0.0336(11) -0.0006(9) 0.0080(9) 0.0007(9) C20 0.0403(12) 0.0388(12) 0.0324(11) 0.0007(9) 0.0107(9) -0.0013(10) C21 0.0357(11) 0.0377(12) 0.0333(11) -0.0002(9) 0.0129(9) -0.0004(9) C22 0.0370(11) 0.0373(11) 0.0326(11) -0.0021(9) 0.0146(9) -0.0045(9) C23 0.0381(12) 0.0369(12) 0.0353(11) -0.0037(9) 0.0164(9) -0.0031(9) C24 0.0333(11) 0.0353(11) 0.0356(11) -0.0030(9) 0.0132(9) -0.0010(9) C25 0.0488(13) 0.0470(13) 0.0317(11) 0.0017(10) 0.0145(10) -0.0030(11) C26 0.0541(15) 0.0726(18) 0.0356(13) 0.0053(12) 0.0076(11) -0.0121(14) C27 0.0605(15) 0.0435(13) 0.0416(13) -0.0053(10) 0.0228(11) 0.0045(11) C28 0.088(2) 0.0554(17) 0.118(3) -0.0057(18) 0.070(2) 0.0124(16) C29 0.0394(12) 0.0416(12) 0.0363(11) 0.0000(10) 0.0149(9) 0.0037(10) O1 0.0373(8) 0.0434(9) 0.0356(9) 0.0001(7) 0.0086(7) 0.0008(7) C30A 0.059(3) 0.061(3) 0.045(3) -0.012(3) 0.009(3) -0.006(2) C31A 0.065(5) 0.083(4) 0.136(7) -0.020(4) 0.017(4) -0.018(3) C30B 0.037(5) 0.061(5) 0.052(6) 0.000(4) 0.003(4) -0.025(4) C31B 0.129(11) 0.096(8) 0.057(7) -0.025(6) 0.012(7) -0.042(8) O2 0.0345(8) 0.0647(11) 0.0342(9) -0.0069(8) 0.0070(7) 0.0052(8) C32 0.0494(14) 0.0552(15) 0.0452(13) -0.0068(12) 0.0093(11) 0.0113(12) C33 0.0591(16) 0.079(2) 0.0456(15) -0.0141(13) 0.0118(12) 0.0176(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C3 1.348(3) . ? N1 N2 1.357(2) . ? N2 C2 1.336(3) . ? N3 C5 1.363(3) . ? N3 C8 1.380(3) . ? N4 C13 1.283(3) . ? N4 C14 1.407(3) . ? N5 C20 1.278(3) . ? N5 C19 1.416(3) . ? N6 C24 1.360(3) . ? N6 C21 1.379(3) . ? C1 C3 1.374(3) . ? C1 C2 1.398(3) . ? C2 C4 1.503(3) . ? C3 C29 1.507(3) . ? C4 C5 1.501(3) . ? C5 C6 1.393(3) . ? C6 C7 1.422(3) . ? C6 C9 1.508(3) . ? C7 C8 1.393(3) . ? C7 C11 1.507(3) . ? C8 C13 1.429(3) . ? C9 C10 1.512(3) . ? C11 C12 1.502(4) . ? C14 C15 1.385(3) . ? C14 C19 1.415(3) . ? C15 C16 1.389(3) . ? C16 C17 1.385(3) . ? C17 C18 1.384(3) . ? C18 C19 1.391(3) . ? C20 C21 1.437(3) . ? C21 C22 1.391(3) . ? C22 C23 1.417(3) . ? C22 C25 1.507(3) . ? C23 C24 1.392(3) . ? C23 C27 1.502(3) . ? C24 C29 1.505(3) . ? C25 C26 1.519(3) . ? C27 C28 1.520(4) . ? O1 C30A 1.426(6) . ? O1 C30B 1.428(10) . ? C30A C31A 1.453(13) . ? C30B C31B 1.47(2) . ? O2 C32 1.415(3) . ? C32 C33 1.494(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 N1 N2 112.05(17) . . ? C2 N2 N1 104.95(16) . . ? C5 N3 C8 109.82(18) . . ? C13 N4 C14 121.27(18) . . ? C20 N5 C19 120.81(18) . . ? C24 N6 C21 109.78(17) . . ? C3 C1 C2 105.60(18) . . ? N2 C2 C1 110.80(19) . . ? N2 C2 C4 121.45(18) . . ? C1 C2 C4 127.74(19) . . ? N1 C3 C1 106.60(18) . . ? N1 C3 C29 121.94(18) . . ? C1 C3 C29 131.46(19) . . ? C5 C4 C2 113.47(18) . . ? N3 C5 C6 108.07(19) . . ? N3 C5 C4 121.37(19) . . ? C6 C5 C4 130.5(2) . . ? C5 C6 C7 107.33(19) . . ? C5 C6 C9 125.7(2) . . ? C7 C6 C9 127.0(2) . . ? C8 C7 C6 107.03(19) . . ? C8 C7 C11 126.2(2) . . ? C6 C7 C11 126.8(2) . . ? N3 C8 C7 107.75(18) . . ? N3 C8 C13 121.52(19) . . ? C7 C8 C13 130.5(2) . . ? C6 C9 C10 112.2(2) . . ? C12 C11 C7 112.9(2) . . ? N4 C13 C8 121.5(2) . . ? C15 C14 N4 124.91(19) . . ? C15 C14 C19 119.52(19) . . ? N4 C14 C19 115.49(18) . . ? C14 C15 C16 120.2(2) . . ? C17 C16 C15 120.3(2) . . ? C18 C17 C16 120.2(2) . . ? C17 C18 C19 120.2(2) . . ? C18 C19 C14 119.56(19) . . ? C18 C19 N5 124.70(19) . . ? C14 C19 N5 115.65(18) . . ? N5 C20 C21 121.79(19) . . ? N6 C21 C22 107.55(18) . . ? N6 C21 C20 121.21(18) . . ? C22 C21 C20 131.0(2) . . ? C21 C22 C23 107.35(18) . . ? C21 C22 C25 126.2(2) . . ? C23 C22 C25 126.35(19) . . ? C24 C23 C22 107.09(18) . . ? C24 C23 C27 124.9(2) . . ? C22 C23 C27 127.92(19) . . ? N6 C24 C23 108.23(18) . . ? N6 C24 C29 122.17(18) . . ? C23 C24 C29 129.58(19) . . ? C22 C25 C26 113.35(19) . . ? C23 C27 C28 112.8(2) . . ? C24 C29 C3 113.43(18) . . ? O1 C30A C31A 110.2(7) . . ? O1 C30B C31B 111.3(12) . . ? O2 C32 C33 110.6(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N O2 0.92(3) 1.86(3) 2.783(2) 179(2) 2 O1 H1O N5 0.82(3) 2.25(3) 2.934(2) 141(3) . O1 H1O N4 0.82(3) 2.27(3) 2.962(2) 143(3) . O2 H2 N2 0.87(3) 1.91(3) 2.778(2) 179(3) . N3 H3 O1 0.92(3) 1.99(3) 2.906(2) 172(3) . N6 H6 O1 0.94(3) 1.99(3) 2.920(2) 171(2) . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 24.88 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.267 _refine_diff_density_min -0.265 _refine_diff_density_rms 0.039 #===END data_4H _database_code_depnum_ccdc_archive 'CCDC 622594' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C29 H35 N6 +, C2 F3 O2 -, H2 O' _chemical_formula_sum 'C31 H37 F3 N6 O3' _chemical_formula_weight 598.67 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.8877(7) _cell_length_b 11.7586(9) _cell_length_c 14.9846(12) _cell_angle_alpha 111.537(6) _cell_angle_beta 91.417(6) _cell_angle_gamma 94.439(6) _cell_volume 1449.9(2) _cell_formula_units_Z 2 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 27128 _cell_measurement_theta_min 1.46 _cell_measurement_theta_max 24.85 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.371 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.7983 _exptl_absorpt_correction_T_max 0.9717 _exptl_absorpt_process_details 'X-RED (Stoe & Cie, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 133(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 'Stoe IPDS II' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 27128 _diffrn_reflns_av_R_equivalents 0.0914 _diffrn_reflns_av_sigmaI/netI 0.0586 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.46 _diffrn_reflns_theta_max 24.85 _reflns_number_total 4999 _reflns_number_gt 3366 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'X-AREA (Stoe & Cie, 2002)' _computing_cell_refinement 'X-AREA (Stoe & Cie, 2002)' _computing_data_reduction 'X-AREA (Stoe & Cie, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0670P)^2^+0.1671P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4999 _refine_ls_number_parameters 426 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0894 _refine_ls_R_factor_gt 0.0533 _refine_ls_wR_factor_ref 0.1339 _refine_ls_wR_factor_gt 0.1194 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F1A F 0.4926(3) 0.8809(4) 0.7130(3) 0.0685(9) Uani 0.729(3) 1 d P A 1 F2A F 0.3388(5) 0.7286(3) 0.6805(3) 0.0790(13) Uani 0.729(3) 1 d P A 1 F3A F 0.2887(6) 0.9004(5) 0.7801(3) 0.1008(17) Uani 0.729(3) 1 d P A 1 F1B F 0.2428(9) 0.7796(10) 0.7455(8) 0.0685(9) Uani 0.271(3) 1 d P A 2 F2B F 0.3814(16) 0.9421(9) 0.7842(8) 0.0790(13) Uani 0.271(3) 1 d P A 2 F3B F 0.4409(18) 0.7870(17) 0.6763(7) 0.1008(17) Uani 0.271(3) 1 d P A 2 N1 N 0.7568(2) 0.9863(2) 0.95321(17) 0.0287(5) Uani 1 1 d . . . N2 N 0.7540(2) 1.0023(2) 0.86777(16) 0.0301(5) Uani 1 1 d . . . N3 N 0.7545(2) 0.6966(2) 0.64782(17) 0.0275(5) Uani 1 1 d . . . N4 N 0.6198(2) 0.46437(19) 0.63007(16) 0.0275(5) Uani 1 1 d . . . N5 N 0.5963(2) 0.4397(2) 0.79507(16) 0.0268(5) Uani 1 1 d . . . N6 N 0.7294(2) 0.6614(2) 0.94741(16) 0.0268(5) Uani 1 1 d . . . O1 O 0.5630(2) 0.71805(16) 0.80863(13) 0.0309(4) Uani 1 1 d . . . O2 O 0.4177(2) 0.84282(18) 0.91523(14) 0.0393(5) Uani 1 1 d . . . O3 O 0.5393(3) 1.1877(2) 0.91289(17) 0.0466(6) Uani 1 1 d . . . C1 C 0.9050(3) 0.8552(2) 0.8653(2) 0.0299(6) Uani 1 1 d . . . H1A H 0.9714 0.7947 0.8437 0.080 Uiso 1 1 calc R . . C2 C 0.8448(3) 0.9211(2) 0.8138(2) 0.0287(6) Uani 1 1 d . . . C3 C 0.8456(3) 0.8985(2) 0.9545(2) 0.0282(6) Uani 1 1 d . . . C4 C 0.8721(3) 0.9154(2) 0.7140(2) 0.0339(6) Uani 1 1 d . . . H4A H 0.9775 0.9424 0.7120 0.080 Uiso 1 1 calc R . . H4B H 0.8117 0.9732 0.7007 0.080 Uiso 1 1 calc R . . C5 C 0.8367(3) 0.7914(2) 0.63529(19) 0.0275(6) Uani 1 1 d . . . C6 C 0.8712(3) 0.7554(2) 0.53958(19) 0.0278(6) Uani 1 1 d . . . C7 C 0.8047(3) 0.6338(2) 0.49193(19) 0.0273(6) Uani 1 1 d . . . C8 C 0.7326(3) 0.5990(2) 0.56124(18) 0.0262(6) Uani 1 1 d . . . C9 C 0.9609(3) 0.8344(3) 0.4964(2) 0.0319(6) Uani 1 1 d . . . H9A H 0.9405 0.9192 0.5292 0.080 Uiso 1 1 calc R . . H9B H 0.9268 0.8101 0.4294 0.080 Uiso 1 1 calc R . . C10 C 1.1305(3) 0.8262(3) 0.5024(3) 0.0441(8) Uani 1 1 d . . . H10A H 1.1656 0.8513 0.5685 0.080 Uiso 1 1 calc R . . H10B H 1.1808 0.8790 0.4743 0.080 Uiso 1 1 calc R . . H10C H 1.1521 0.7430 0.4682 0.080 Uiso 1 1 calc R . . C11 C 0.8042(3) 0.5569(3) 0.38658(19) 0.0305(6) Uani 1 1 d . . . H11A H 0.7967 0.6100 0.3504 0.080 Uiso 1 1 calc R . . H11B H 0.7150 0.4987 0.3691 0.080 Uiso 1 1 calc R . . C12 C 0.9426(3) 0.4866(3) 0.3571(2) 0.0463(8) Uani 1 1 d . . . H12A H 1.0317 0.5433 0.3731 0.080 Uiso 1 1 calc R . . H12B H 0.9344 0.4408 0.2891 0.080 Uiso 1 1 calc R . . H12C H 0.9491 0.4312 0.3905 0.080 Uiso 1 1 calc R . . C13 C 0.6607(3) 0.4832(2) 0.55425(19) 0.0274(6) Uani 1 1 d . . . H13 H 0.6430 0.4204 0.4943 0.080 Uiso 1 1 calc R . . C14 C 0.5512(3) 0.3494(2) 0.62467(19) 0.0255(6) Uani 1 1 d . . . C15 C 0.4955(3) 0.2514(2) 0.5419(2) 0.0286(6) Uani 1 1 d . . . H15 H 0.5011 0.2583 0.4822 0.080 Uiso 1 1 calc R . . C16 C 0.4316(3) 0.1435(2) 0.5486(2) 0.0319(6) Uani 1 1 d . . . H16 H 0.3951 0.0784 0.4930 0.080 Uiso 1 1 calc R . . C17 C 0.4215(3) 0.1312(3) 0.6367(2) 0.0339(6) Uani 1 1 d . . . H17 H 0.3795 0.0580 0.6399 0.080 Uiso 1 1 calc R . . C18 C 0.4741(3) 0.2282(2) 0.7206(2) 0.0317(6) Uani 1 1 d . . . H18 H 0.4661 0.2210 0.7801 0.080 Uiso 1 1 calc R . . C19 C 0.5387(3) 0.3361(2) 0.71410(19) 0.0259(6) Uani 1 1 d . . . C20 C 0.6257(3) 0.4450(2) 0.88333(18) 0.0261(6) Uani 1 1 d . . . H20 H 0.6018 0.3748 0.8968 0.080 Uiso 1 1 calc R . . C21 C 0.6903(3) 0.5499(2) 0.95751(19) 0.0263(6) Uani 1 1 d . . . C22 C 0.7446(3) 0.5612(2) 1.05052(19) 0.0262(6) Uani 1 1 d . . . C23 C 0.8160(3) 0.6801(2) 1.09478(19) 0.0270(6) Uani 1 1 d . . . C24 C 0.8039(3) 0.7389(2) 1.02889(19) 0.0263(6) Uani 1 1 d . . . C25 C 0.7310(3) 0.4618(2) 1.0911(2) 0.0303(6) Uani 1 1 d . . . H25A H 0.6394 0.4085 1.0635 0.080 Uiso 1 1 calc R . . H25B H 0.7219 0.4989 1.1600 0.080 Uiso 1 1 calc R . . C26 C 0.8653(3) 0.3848(3) 1.0717(2) 0.0411(7) Uani 1 1 d . . . H26A H 0.8730 0.3454 1.0036 0.080 Uiso 1 1 calc R . . H26B H 0.8512 0.3235 1.0997 0.080 Uiso 1 1 calc R . . H26C H 0.9563 0.4368 1.0995 0.080 Uiso 1 1 calc R . . C27 C 0.8893(3) 0.7385(3) 1.19463(19) 0.0319(6) Uani 1 1 d . . . H27A H 0.8407 0.7003 1.2351 0.080 Uiso 1 1 calc R . . H27B H 0.8710 0.8246 1.2199 0.080 Uiso 1 1 calc R . . C28 C 1.0598(3) 0.7296(3) 1.2021(2) 0.0438(7) Uani 1 1 d . . . H28A H 1.0798 0.6449 1.1770 0.080 Uiso 1 1 calc R . . H28B H 1.0962 0.7666 1.2682 0.080 Uiso 1 1 calc R . . H28C H 1.1102 0.7718 1.1656 0.080 Uiso 1 1 calc R . . C29 C 0.8629(3) 0.8674(2) 1.0418(2) 0.0320(6) Uani 1 1 d . . . H29A H 0.8106 0.9243 1.0930 0.080 Uiso 1 1 calc R . . H29B H 0.9692 0.8793 1.0622 0.080 Uiso 1 1 calc R . . C30 C 0.4657(3) 0.7928(2) 0.83463(19) 0.0283(6) Uani 1 1 d . A . C31 C 0.3912(3) 0.8257(3) 0.7544(2) 0.0338(6) Uani 1 1 d . . . H5 H 0.619(3) 0.506(3) 0.780(2) 0.031(7) Uiso 1 1 d . . . H3 H 0.706(4) 0.700(3) 0.699(3) 0.044(9) Uiso 1 1 d . . . H6 H 0.688(4) 0.689(3) 0.900(3) 0.067(11) Uiso 1 1 d . . . H1 H 0.702(4) 1.035(3) 1.004(3) 0.053(10) Uiso 1 1 d . . . H3A H 0.609(5) 1.128(4) 0.886(3) 0.077(13) Uiso 1 1 d . . . H3B H 0.534(5) 1.184(4) 0.979(4) 0.100(15) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1A 0.0622(17) 0.096(2) 0.069(2) 0.062(2) -0.0192(15) -0.0172(17) F2A 0.133(3) 0.0468(17) 0.049(2) 0.0196(15) -0.052(2) -0.0309(19) F3A 0.119(3) 0.157(4) 0.0457(19) 0.039(2) 0.025(2) 0.115(3) F1B 0.0622(17) 0.096(2) 0.069(2) 0.062(2) -0.0192(15) -0.0172(17) F2B 0.133(3) 0.0468(17) 0.049(2) 0.0196(15) -0.052(2) -0.0309(19) F3B 0.119(3) 0.157(4) 0.0457(19) 0.039(2) 0.025(2) 0.115(3) N1 0.0346(12) 0.0273(12) 0.0232(12) 0.0076(10) 0.0034(10) 0.0047(10) N2 0.0365(12) 0.0290(12) 0.0241(12) 0.0089(10) 0.0030(9) 0.0031(9) N3 0.0311(11) 0.0283(12) 0.0223(12) 0.0081(10) 0.0052(10) 0.0023(9) N4 0.0304(11) 0.0266(11) 0.0257(12) 0.0101(10) 0.0025(9) 0.0014(9) N5 0.0305(11) 0.0262(12) 0.0246(12) 0.0111(10) 0.0000(9) 0.0001(9) N6 0.0290(11) 0.0287(12) 0.0236(12) 0.0108(10) 0.0002(9) 0.0031(9) O1 0.0349(10) 0.0313(10) 0.0267(10) 0.0101(8) 0.0042(8) 0.0071(8) O2 0.0497(12) 0.0426(12) 0.0282(11) 0.0135(9) 0.0104(9) 0.0153(9) O3 0.0636(14) 0.0483(13) 0.0366(13) 0.0219(11) 0.0095(11) 0.0232(11) C1 0.0332(14) 0.0256(13) 0.0285(15) 0.0070(12) 0.0004(11) 0.0042(11) C2 0.0323(13) 0.0240(13) 0.0260(14) 0.0055(11) 0.0034(11) -0.0012(10) C3 0.0317(13) 0.0230(13) 0.0284(15) 0.0081(11) -0.0012(11) 0.0012(10) C4 0.0429(15) 0.0282(14) 0.0290(15) 0.0094(12) 0.0056(12) -0.0004(12) C5 0.0290(13) 0.0274(14) 0.0284(15) 0.0127(12) 0.0028(11) 0.0045(11) C6 0.0293(13) 0.0304(14) 0.0265(14) 0.0131(12) 0.0032(11) 0.0057(11) C7 0.0273(12) 0.0293(14) 0.0267(15) 0.0118(12) 0.0010(11) 0.0033(10) C8 0.0284(13) 0.0264(13) 0.0209(13) 0.0050(11) 0.0007(10) 0.0038(10) C9 0.0345(14) 0.0344(15) 0.0305(15) 0.0159(13) 0.0064(12) 0.0042(12) C10 0.0326(15) 0.0473(18) 0.059(2) 0.0286(17) 0.0091(14) -0.0013(13) C11 0.0345(14) 0.0363(15) 0.0223(14) 0.0124(12) 0.0027(11) 0.0034(11) C12 0.0412(16) 0.055(2) 0.0331(17) 0.0039(15) 0.0055(13) 0.0111(14) C13 0.0268(12) 0.0308(14) 0.0263(15) 0.0118(12) 0.0029(11) 0.0057(10) C14 0.0249(12) 0.0261(13) 0.0258(14) 0.0094(11) 0.0024(10) 0.0049(10) C15 0.0304(13) 0.0283(14) 0.0275(15) 0.0107(12) 0.0004(11) 0.0043(11) C16 0.0317(14) 0.0293(14) 0.0306(16) 0.0062(12) -0.0013(11) 0.0037(11) C17 0.0348(14) 0.0283(15) 0.0364(17) 0.0104(13) -0.0008(12) -0.0005(11) C18 0.0300(13) 0.0349(15) 0.0320(16) 0.0144(13) 0.0014(11) 0.0033(11) C19 0.0284(13) 0.0223(13) 0.0240(14) 0.0050(11) 0.0014(11) 0.0023(10) C20 0.0249(12) 0.0303(14) 0.0235(14) 0.0095(12) 0.0038(10) 0.0058(10) C21 0.0250(12) 0.0283(14) 0.0269(14) 0.0114(12) 0.0031(10) 0.0038(10) C22 0.0252(12) 0.0311(14) 0.0238(14) 0.0110(12) 0.0054(10) 0.0056(10) C23 0.0267(12) 0.0312(14) 0.0235(14) 0.0100(12) 0.0031(10) 0.0061(11) C24 0.0260(12) 0.0280(14) 0.0229(14) 0.0063(11) 0.0033(10) 0.0050(10) C25 0.0333(14) 0.0347(15) 0.0272(15) 0.0156(12) 0.0036(11) 0.0065(11) C26 0.0399(15) 0.0466(18) 0.0467(19) 0.0267(16) 0.0062(14) 0.0127(13) C27 0.0338(14) 0.0387(16) 0.0218(14) 0.0095(12) 0.0006(11) 0.0029(12) C28 0.0354(15) 0.056(2) 0.0371(18) 0.0141(15) -0.0035(13) 0.0036(14) C29 0.0408(15) 0.0263(14) 0.0269(15) 0.0078(12) -0.0009(12) 0.0021(11) C30 0.0302(13) 0.0279(14) 0.0239(14) 0.0063(11) 0.0047(11) 0.0018(11) C31 0.0382(15) 0.0322(15) 0.0277(15) 0.0063(13) 0.0019(12) 0.0078(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1A C31 1.361(4) . ? F2A C31 1.308(4) . ? F3A C31 1.281(4) . ? F1B C31 1.370(8) . ? F2B C31 1.285(11) . ? F3B C31 1.198(9) . ? N1 C3 1.352(3) . ? N1 N2 1.360(3) . ? N2 C2 1.342(3) . ? N3 C5 1.359(3) . ? N3 C8 1.378(3) . ? N4 C13 1.290(3) . ? N4 C14 1.412(3) . ? N5 C20 1.319(3) . ? N5 C19 1.416(3) . ? N6 C24 1.345(4) . ? N6 C21 1.393(3) . ? O1 C30 1.247(3) . ? O2 C30 1.237(3) . ? C1 C3 1.378(4) . ? C1 C2 1.402(4) . ? C2 C4 1.498(4) . ? C3 C29 1.491(4) . ? C4 C5 1.505(4) . ? C5 C6 1.388(4) . ? C6 C7 1.415(4) . ? C6 C9 1.507(4) . ? C7 C8 1.400(4) . ? C7 C11 1.504(4) . ? C8 C13 1.425(4) . ? C9 C10 1.520(4) . ? C11 C12 1.519(4) . ? C14 C15 1.394(4) . ? C14 C19 1.411(4) . ? C15 C16 1.388(4) . ? C16 C17 1.384(4) . ? C17 C18 1.391(4) . ? C18 C19 1.389(4) . ? C20 C21 1.392(4) . ? C21 C22 1.419(4) . ? C22 C23 1.399(4) . ? C22 C25 1.501(4) . ? C23 C24 1.404(4) . ? C23 C27 1.504(4) . ? C24 C29 1.500(4) . ? C25 C26 1.523(4) . ? C27 C28 1.531(4) . ? C30 C31 1.542(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 N1 N2 112.8(2) . . ? C2 N2 N1 104.4(2) . . ? C5 N3 C8 109.4(2) . . ? C13 N4 C14 121.6(2) . . ? C20 N5 C19 127.8(2) . . ? C24 N6 C21 108.8(2) . . ? C3 C1 C2 105.9(2) . . ? N2 C2 C1 110.9(2) . . ? N2 C2 C4 119.2(2) . . ? C1 C2 C4 129.8(2) . . ? N1 C3 C1 106.0(2) . . ? N1 C3 C29 120.8(2) . . ? C1 C3 C29 133.2(2) . . ? C2 C4 C5 115.7(2) . . ? N3 C5 C6 108.7(2) . . ? N3 C5 C4 123.3(2) . . ? C6 C5 C4 128.0(2) . . ? C5 C6 C7 107.3(2) . . ? C5 C6 C9 125.2(2) . . ? C7 C6 C9 127.5(2) . . ? C8 C7 C6 106.8(2) . . ? C8 C7 C11 125.7(2) . . ? C6 C7 C11 127.4(2) . . ? N3 C8 C7 107.8(2) . . ? N3 C8 C13 121.7(2) . . ? C7 C8 C13 130.2(2) . . ? C6 C9 C10 113.7(2) . . ? C7 C11 C12 114.5(2) . . ? N4 C13 C8 120.8(2) . . ? C15 C14 C19 118.3(2) . . ? C15 C14 N4 127.0(2) . . ? C19 C14 N4 114.7(2) . . ? C16 C15 C14 120.0(3) . . ? C17 C16 C15 121.0(3) . . ? C16 C17 C18 120.1(3) . . ? C19 C18 C17 119.0(3) . . ? C18 C19 C14 121.5(2) . . ? C18 C19 N5 123.3(2) . . ? C14 C19 N5 115.2(2) . . ? N5 C20 C21 123.7(2) . . ? C20 C21 N6 124.0(2) . . ? C20 C21 C22 128.1(2) . . ? N6 C21 C22 107.5(2) . . ? C23 C22 C21 107.0(2) . . ? C23 C22 C25 127.3(2) . . ? C21 C22 C25 125.7(2) . . ? C22 C23 C24 107.1(2) . . ? C22 C23 C27 127.9(2) . . ? C24 C23 C27 125.0(2) . . ? N6 C24 C23 109.6(2) . . ? N6 C24 C29 122.5(2) . . ? C23 C24 C29 127.9(2) . . ? C22 C25 C26 113.0(2) . . ? C23 C27 C28 115.1(2) . . ? C3 C29 C24 114.9(2) . . ? O2 C30 O1 129.5(3) . . ? O2 C30 C31 114.9(2) . . ? O1 C30 C31 115.5(2) . . ? F3B C31 F2B 112.1(10) . . ? F3A C31 F2A 109.4(4) . . ? F3A C31 F1A 104.0(4) . . ? F2A C31 F1A 101.3(3) . . ? F3B C31 F1B 107.7(10) . . ? F2B C31 F1B 102.5(8) . . ? F3B C31 C30 117.7(5) . . ? F3A C31 C30 115.9(3) . . ? F2B C31 C30 109.7(5) . . ? F2A C31 C30 112.6(2) . . ? F1A C31 C30 112.3(2) . . ? F1B C31 C30 105.8(4) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O2 0.94(4) 1.92(4) 2.838(3) 164(3) 2_677 N3 H3 O1 0.87(3) 2.07(4) 2.931(3) 170(3) . N5 H5 O1 0.90(3) 2.46(3) 3.242(3) 145(2) . N5 H5 N4 0.90(3) 2.11(3) 2.605(3) 113(2) . N6 H6 O1 0.96(4) 1.88(4) 2.824(3) 166(3) . O3 H3A N2 0.95(5) 1.99(5) 2.912(3) 164(4) . O3 H3B O2 1.01(5) 1.78(5) 2.749(3) 161(4) 2_677 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 24.85 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.276 _refine_diff_density_min -0.318 _refine_diff_density_rms 0.050