# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and The Centre National de la Recherche Scientifique, 2010 data_global _journal_coden_Cambridge 440 loop_ _publ_author_name 'Hosseini, Mir Wais' 'Ferlay, Sylvie' 'Dechambenoit, Pierre' 'Kyritsakas, Nathalie' _publ_contact_author_name 'Hosseini, Mir Wais' _publ_contact_author_email hosseini@chimie.u-strasbg.fr _publ_section_title ; Amidinium based ionic liquids ; # Attachment '- 15.cif' data_e965a _database_code_depnum_ccdc_archive 'CCDC 753161' #TrackingRef '- 15.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H20 B, C10 H13 N2' _chemical_formula_sum 'C34 H33 B N2' _chemical_formula_weight 480.43 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.7552(9) _cell_length_b 15.9976(13) _cell_length_c 17.3840(16) _cell_angle_alpha 90.00 _cell_angle_beta 99.527(2) _cell_angle_gamma 90.00 _cell_volume 2675.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2330 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 22.83 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.193 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1024 _exptl_absorpt_coefficient_mu 0.068 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9932 _exptl_absorpt_correction_T_max 0.9959 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17812 _diffrn_reflns_av_R_equivalents 0.0416 _diffrn_reflns_av_sigmaI/netI 0.0599 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.38 _diffrn_reflns_theta_max 27.56 _reflns_number_total 6100 _reflns_number_gt 3458 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0655P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0050(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6100 _refine_ls_number_parameters 337 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1043 _refine_ls_R_factor_gt 0.0487 _refine_ls_wR_factor_ref 0.1414 _refine_ls_wR_factor_gt 0.1115 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _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 C1 C 0.71284(19) 0.21023(11) 0.08406(10) 0.0311(4) Uani 1 1 d . . . N1 N 0.60967(16) 0.16479(9) 0.04786(9) 0.0383(4) Uani 1 1 d . . . H1 H 0.5334 0.1859 0.0207 0.046 Uiso 1 1 calc R . . C2 C 0.6359(2) 0.07536(11) 0.05777(12) 0.0440(5) Uani 1 1 d . . . H2A H 0.6374 0.0475 0.0071 0.053 Uiso 1 1 calc R . . H2B H 0.5652 0.0481 0.0842 0.053 Uiso 1 1 calc R . . C3 C 0.7800(2) 0.07393(11) 0.10919(12) 0.0407(5) Uani 1 1 d . . . H3A H 0.7767 0.0454 0.1594 0.049 Uiso 1 1 calc R . . H3B H 0.8489 0.0454 0.0824 0.049 Uiso 1 1 calc R . . N2 N 0.81365(16) 0.16297(9) 0.12122(9) 0.0362(4) Uani 1 1 d . . . C4 C 0.9372(2) 0.18916(12) 0.17538(13) 0.0483(6) Uani 1 1 d . . . H4A H 1.0186 0.1865 0.1492 0.072 Uiso 1 1 calc R . . H4B H 0.9510 0.1519 0.2208 0.072 Uiso 1 1 calc R . . H4C H 0.9246 0.2466 0.1925 0.072 Uiso 1 1 calc R . . C5 C 0.71286(19) 0.30192(10) 0.08033(11) 0.0314(4) Uani 1 1 d . . . C6 C 0.8309(2) 0.34487(11) 0.06695(12) 0.0406(5) Uani 1 1 d . . . H6 H 0.9150 0.3156 0.0649 0.049 Uiso 1 1 calc R . . C7 C 0.8243(3) 0.43056(12) 0.05669(13) 0.0520(6) Uani 1 1 d . . . H7 H 0.9037 0.4604 0.0465 0.062 Uiso 1 1 calc R . . C8 C 0.7023(3) 0.47291(12) 0.06123(13) 0.0541(6) Uani 1 1 d . . . H8 H 0.6985 0.5319 0.0545 0.065 Uiso 1 1 calc R . . C9 C 0.5865(2) 0.43066(12) 0.07530(12) 0.0487(6) Uani 1 1 d . . . H9 H 0.5036 0.4605 0.0789 0.058 Uiso 1 1 calc R . . C10 C 0.5903(2) 0.34452(11) 0.08422(11) 0.0392(5) Uani 1 1 d . . . H10 H 0.5098 0.3150 0.0929 0.047 Uiso 1 1 calc R . . B1 B 0.8187(2) 0.76938(11) 0.09344(12) 0.0295(5) Uani 1 1 d . . . C11 C 0.90062(19) 0.68705(10) 0.13551(10) 0.0293(4) Uani 1 1 d . . . C12 C 0.8525(2) 0.63509(11) 0.19014(11) 0.0360(5) Uani 1 1 d . . . H12 H 0.7677 0.6489 0.2071 0.043 Uiso 1 1 calc R . . C13 C 0.9239(2) 0.56405(12) 0.22057(11) 0.0414(5) Uani 1 1 d . . . H13 H 0.8865 0.5301 0.2569 0.050 Uiso 1 1 calc R . . C14 C 1.0485(2) 0.54247(11) 0.19844(11) 0.0379(5) Uani 1 1 d . . . H14 H 1.0964 0.4933 0.2183 0.045 Uiso 1 1 calc R . . C15 C 1.1024(2) 0.59343(11) 0.14692(12) 0.0395(5) Uani 1 1 d . . . H15 H 1.1891 0.5802 0.1319 0.047 Uiso 1 1 calc R . . C16 C 1.0300(2) 0.66418(10) 0.11698(11) 0.0365(5) Uani 1 1 d . . . H16 H 1.0701 0.6988 0.0822 0.044 Uiso 1 1 calc R . . C17 C 0.78855(19) 0.75916(10) -0.00208(10) 0.0303(4) Uani 1 1 d . . . C18 C 0.80557(19) 0.68538(11) -0.04304(11) 0.0353(4) Uani 1 1 d . . . H18 H 0.8452 0.6381 -0.0147 0.042 Uiso 1 1 calc R . . C19 C 0.7668(2) 0.67857(14) -0.12349(12) 0.0462(5) Uani 1 1 d . . . H19 H 0.7809 0.6274 -0.1487 0.055 Uiso 1 1 calc R . . C20 C 0.7079(2) 0.74550(15) -0.16695(13) 0.0522(6) Uani 1 1 d . . . H20 H 0.6803 0.7407 -0.2218 0.063 Uiso 1 1 calc R . . C21 C 0.6899(2) 0.81961(14) -0.12917(12) 0.0466(5) Uani 1 1 d . . . H21 H 0.6502 0.8665 -0.1582 0.056 Uiso 1 1 calc R . . C22 C 0.72980(19) 0.82588(11) -0.04873(11) 0.0365(4) Uani 1 1 d . . . H22 H 0.7167 0.8777 -0.0243 0.044 Uiso 1 1 calc R . . C23 C 0.66278(19) 0.78134(10) 0.11644(10) 0.0286(4) Uani 1 1 d . . . C24 C 0.5658(2) 0.71557(10) 0.10402(11) 0.0323(4) Uani 1 1 d . . . H24 H 0.5947 0.6637 0.0854 0.039 Uiso 1 1 calc R . . C25 C 0.4301(2) 0.72256(11) 0.11764(11) 0.0387(5) Uani 1 1 d . . . H25 H 0.3695 0.6758 0.1093 0.046 Uiso 1 1 calc R . . C26 C 0.3826(2) 0.79752(12) 0.14342(12) 0.0427(5) Uani 1 1 d . . . H26 H 0.2899 0.8028 0.1530 0.051 Uiso 1 1 calc R . . C27 C 0.4732(2) 0.86414(12) 0.15484(12) 0.0441(5) Uani 1 1 d . . . H27 H 0.4421 0.9164 0.1715 0.053 Uiso 1 1 calc R . . C28 C 0.6097(2) 0.85571(11) 0.14219(11) 0.0369(5) Uani 1 1 d . . . H28 H 0.6697 0.9027 0.1515 0.044 Uiso 1 1 calc R . . C29 C 0.92198(19) 0.84942(10) 0.12051(11) 0.0303(4) Uani 1 1 d . . . C30 C 1.0014(2) 0.89070(10) 0.07222(12) 0.0353(4) Uani 1 1 d . . . H30 H 0.9925 0.8741 0.0192 0.042 Uiso 1 1 calc R . . C31 C 1.0930(2) 0.95523(11) 0.09874(13) 0.0414(5) Uani 1 1 d . . . H31 H 1.1447 0.9815 0.0637 0.050 Uiso 1 1 calc R . . C32 C 1.1094(2) 0.98119(11) 0.17504(13) 0.0429(5) Uani 1 1 d . . . H32 H 1.1711 1.0256 0.1930 0.052 Uiso 1 1 calc R . . C33 C 1.0345(2) 0.94148(11) 0.22528(12) 0.0425(5) Uani 1 1 d . . . H33 H 1.0452 0.9582 0.2784 0.051 Uiso 1 1 calc R . . C34 C 0.9435(2) 0.87709(11) 0.19822(11) 0.0383(5) Uani 1 1 d . . . H34 H 0.8935 0.8506 0.2339 0.046 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 C1 0.0256(10) 0.0385(9) 0.0297(10) -0.0002(7) 0.0058(8) -0.0008(8) N1 0.0276(9) 0.0362(8) 0.0477(11) 0.0036(7) -0.0040(8) -0.0021(7) C2 0.0402(13) 0.0337(9) 0.0542(14) 0.0044(9) -0.0033(10) -0.0028(9) C3 0.0365(12) 0.0354(10) 0.0495(13) 0.0023(8) 0.0048(10) -0.0003(9) N2 0.0276(9) 0.0383(8) 0.0405(10) 0.0015(7) -0.0009(7) 0.0004(7) C4 0.0357(13) 0.0550(12) 0.0491(14) -0.0006(10) -0.0080(10) -0.0018(10) C5 0.0292(11) 0.0327(9) 0.0325(11) -0.0019(7) 0.0055(8) -0.0012(8) C6 0.0346(12) 0.0426(10) 0.0445(12) -0.0024(9) 0.0059(10) -0.0056(9) C7 0.0557(16) 0.0409(11) 0.0589(15) -0.0041(10) 0.0078(12) -0.0158(11) C8 0.0723(18) 0.0346(10) 0.0548(15) -0.0060(9) 0.0091(13) -0.0016(11) C9 0.0556(15) 0.0438(11) 0.0479(14) 0.0004(9) 0.0120(11) 0.0135(11) C10 0.0374(12) 0.0430(10) 0.0382(12) 0.0006(8) 0.0092(9) 0.0023(9) B1 0.0284(12) 0.0285(9) 0.0311(12) 0.0010(8) 0.0035(9) -0.0013(8) C11 0.0296(10) 0.0279(8) 0.0289(10) -0.0028(7) 0.0009(8) -0.0027(8) C12 0.0355(12) 0.0414(10) 0.0324(11) 0.0055(8) 0.0092(9) 0.0055(8) C13 0.0445(13) 0.0433(10) 0.0370(12) 0.0111(8) 0.0089(10) 0.0061(9) C14 0.0381(12) 0.0361(9) 0.0371(11) 0.0033(8) -0.0005(9) 0.0069(9) C15 0.0297(11) 0.0397(10) 0.0486(13) 0.0017(9) 0.0056(9) 0.0053(9) C16 0.0320(11) 0.0346(9) 0.0437(12) 0.0054(8) 0.0085(9) -0.0012(8) C17 0.0223(10) 0.0372(9) 0.0311(10) 0.0019(7) 0.0036(8) -0.0035(8) C18 0.0259(11) 0.0427(10) 0.0369(12) -0.0048(8) 0.0046(8) -0.0039(8) C19 0.0330(12) 0.0648(13) 0.0413(13) -0.0158(10) 0.0078(10) -0.0086(11) C20 0.0348(13) 0.0914(17) 0.0300(12) -0.0024(11) 0.0043(10) -0.0172(12) C21 0.0327(12) 0.0674(14) 0.0379(13) 0.0166(10) 0.0005(9) -0.0077(11) C22 0.0304(11) 0.0433(10) 0.0352(11) 0.0056(8) 0.0037(9) -0.0031(9) C23 0.0282(10) 0.0304(8) 0.0260(10) 0.0015(7) 0.0010(8) 0.0012(7) C24 0.0312(11) 0.0294(8) 0.0356(11) 0.0010(7) 0.0032(9) -0.0012(8) C25 0.0322(12) 0.0418(10) 0.0414(12) 0.0071(8) 0.0041(9) -0.0058(9) C26 0.0331(12) 0.0560(12) 0.0405(13) 0.0034(9) 0.0103(10) 0.0042(10) C27 0.0409(13) 0.0443(11) 0.0487(13) -0.0105(9) 0.0122(10) 0.0058(10) C28 0.0356(12) 0.0331(9) 0.0423(12) -0.0064(8) 0.0073(9) -0.0017(8) C29 0.0269(10) 0.0282(8) 0.0342(11) 0.0037(7) 0.0004(8) 0.0034(7) C30 0.0323(11) 0.0333(9) 0.0405(12) 0.0023(8) 0.0070(9) 0.0005(8) C31 0.0293(11) 0.0370(10) 0.0579(15) 0.0058(9) 0.0071(10) -0.0038(9) C32 0.0326(12) 0.0345(9) 0.0560(14) 0.0001(9) -0.0094(10) -0.0037(9) C33 0.0451(13) 0.0400(10) 0.0366(12) 0.0004(8) -0.0105(10) -0.0039(9) C34 0.0412(12) 0.0367(10) 0.0343(11) 0.0054(8) -0.0015(9) -0.0054(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.314(2) . ? C1 N2 1.321(2) . ? C1 C5 1.468(2) . ? N1 C2 1.459(2) . ? N1 H1 0.8800 . ? C2 C3 1.536(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 N2 1.469(2) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? N2 C4 1.462(2) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 C10 1.387(3) . ? C5 C6 1.393(3) . ? C6 C7 1.382(3) . ? C6 H6 0.9500 . ? C7 C8 1.384(3) . ? C7 H7 0.9500 . ? C8 C9 1.372(3) . ? C8 H8 0.9500 . ? C9 C10 1.387(3) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? B1 C17 1.646(3) . ? B1 C23 1.646(3) . ? B1 C11 1.648(3) . ? B1 C29 1.649(3) . ? C11 C12 1.400(2) . ? C11 C16 1.402(3) . ? C12 C13 1.391(2) . ? C12 H12 0.9500 . ? C13 C14 1.378(3) . ? C13 H13 0.9500 . ? C14 C15 1.378(3) . ? C14 H14 0.9500 . ? C15 C16 1.389(2) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 C18 1.402(2) . ? C17 C22 1.404(2) . ? C18 C19 1.391(3) . ? C18 H18 0.9500 . ? C19 C20 1.380(3) . ? C19 H19 0.9500 . ? C20 C21 1.381(3) . ? C20 H20 0.9500 . ? C21 C22 1.392(3) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 C28 1.401(2) . ? C23 C24 1.408(2) . ? C24 C25 1.387(3) . ? C24 H24 0.9500 . ? C25 C26 1.386(3) . ? C25 H25 0.9500 . ? C26 C27 1.377(3) . ? C26 H26 0.9500 . ? C27 C28 1.392(3) . ? C27 H27 0.9500 . ? C28 H28 0.9500 . ? C29 C30 1.399(2) . ? C29 C34 1.404(3) . ? C30 C31 1.393(3) . ? C30 H30 0.9500 . ? C31 C32 1.374(3) . ? C31 H31 0.9500 . ? C32 C33 1.383(3) . ? C32 H32 0.9500 . ? C33 C34 1.390(3) . ? C33 H33 0.9500 . ? C34 H34 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 N1 C1 N2 111.51(15) . . ? N1 C1 C5 122.48(17) . . ? N2 C1 C5 125.99(17) . . ? C1 N1 C2 112.37(16) . . ? C1 N1 H1 123.8 . . ? C2 N1 H1 123.8 . . ? N1 C2 C3 102.06(14) . . ? N1 C2 H2A 111.4 . . ? C3 C2 H2A 111.4 . . ? N1 C2 H2B 111.4 . . ? C3 C2 H2B 111.4 . . ? H2A C2 H2B 109.2 . . ? N2 C3 C2 103.29(14) . . ? N2 C3 H3A 111.1 . . ? C2 C3 H3A 111.1 . . ? N2 C3 H3B 111.1 . . ? C2 C3 H3B 111.1 . . ? H3A C3 H3B 109.1 . . ? C1 N2 C4 128.19(16) . . ? C1 N2 C3 110.76(15) . . ? C4 N2 C3 120.69(15) . . ? N2 C4 H4A 109.5 . . ? N2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C10 C5 C6 120.57(17) . . ? C10 C5 C1 118.83(16) . . ? C6 C5 C1 120.41(17) . . ? C7 C6 C5 119.3(2) . . ? C7 C6 H6 120.4 . . ? C5 C6 H6 120.4 . . ? C6 C7 C8 120.0(2) . . ? C6 C7 H7 120.0 . . ? C8 C7 H7 120.0 . . ? C9 C8 C7 120.68(19) . . ? C9 C8 H8 119.7 . . ? C7 C8 H8 119.7 . . ? C8 C9 C10 120.1(2) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? C9 C10 C5 119.35(19) . . ? C9 C10 H10 120.3 . . ? C5 C10 H10 120.3 . . ? C17 B1 C23 103.81(14) . . ? C17 B1 C11 111.16(14) . . ? C23 B1 C11 112.63(14) . . ? C17 B1 C29 111.33(14) . . ? C23 B1 C29 112.70(14) . . ? C11 B1 C29 105.39(14) . . ? C12 C11 C16 114.61(16) . . ? C12 C11 B1 125.68(16) . . ? C16 C11 B1 119.72(15) . . ? C13 C12 C11 122.70(18) . . ? C13 C12 H12 118.7 . . ? C11 C12 H12 118.7 . . ? C14 C13 C12 120.51(18) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C15 C14 C13 118.82(17) . . ? C15 C14 H14 120.6 . . ? C13 C14 H14 120.6 . . ? C14 C15 C16 120.05(19) . . ? C14 C15 H15 120.0 . . ? C16 C15 H15 120.0 . . ? C15 C16 C11 123.22(17) . . ? C15 C16 H16 118.4 . . ? C11 C16 H16 118.4 . . ? C18 C17 C22 114.70(17) . . ? C18 C17 B1 125.40(15) . . ? C22 C17 B1 119.66(15) . . ? C19 C18 C17 122.74(18) . . ? C19 C18 H18 118.6 . . ? C17 C18 H18 118.6 . . ? C20 C19 C18 120.59(19) . . ? C20 C19 H19 119.7 . . ? C18 C19 H19 119.7 . . ? C19 C20 C21 118.7(2) . . ? C19 C20 H20 120.7 . . ? C21 C20 H20 120.7 . . ? C20 C21 C22 120.23(19) . . ? C20 C21 H21 119.9 . . ? C22 C21 H21 119.9 . . ? C21 C22 C17 123.03(18) . . ? C21 C22 H22 118.5 . . ? C17 C22 H22 118.5 . . ? C28 C23 C24 114.14(17) . . ? C28 C23 B1 125.58(15) . . ? C24 C23 B1 120.04(15) . . ? C25 C24 C23 123.36(16) . . ? C25 C24 H24 118.3 . . ? C23 C24 H24 118.3 . . ? C26 C25 C24 120.27(18) . . ? C26 C25 H25 119.9 . . ? C24 C25 H25 119.9 . . ? C27 C26 C25 118.38(19) . . ? C27 C26 H26 120.8 . . ? C25 C26 H26 120.8 . . ? C26 C27 C28 120.64(18) . . ? C26 C27 H27 119.7 . . ? C28 C27 H27 119.7 . . ? C27 C28 C23 123.18(17) . . ? C27 C28 H28 118.4 . . ? C23 C28 H28 118.4 . . ? C30 C29 C34 114.79(17) . . ? C30 C29 B1 124.63(16) . . ? C34 C29 B1 120.41(16) . . ? C31 C30 C29 122.69(19) . . ? C31 C30 H30 118.7 . . ? C29 C30 H30 118.7 . . ? C32 C31 C30 120.62(19) . . ? C32 C31 H31 119.7 . . ? C30 C31 H31 119.7 . . ? C31 C32 C33 118.80(18) . . ? C31 C32 H32 120.6 . . ? C33 C32 H32 120.6 . . ? C32 C33 C34 120.10(19) . . ? C32 C33 H33 119.9 . . ? C34 C33 H33 119.9 . . ? C33 C34 C29 122.99(19) . . ? C33 C34 H34 118.5 . . ? C29 C34 H34 118.5 . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 27.56 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.185 _refine_diff_density_min -0.210 _refine_diff_density_rms 0.047 # Attachment '- 18.cif' data_e732a _database_code_depnum_ccdc_archive 'CCDC 753162' #TrackingRef '- 18.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H15 N2, I' _chemical_formula_sum 'C11 H15 I N2' _chemical_formula_weight 302.15 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.60500(10) _cell_length_b 15.5700(3) _cell_length_c 11.7069(2) _cell_angle_alpha 90.00 _cell_angle_beta 97.5510(10) _cell_angle_gamma 90.00 _cell_volume 1193.50(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7517 _cell_measurement_theta_min 2.62 _cell_measurement_theta_max 29.30 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.682 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 2.649 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6193 _exptl_absorpt_correction_T_max 0.6615 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18778 _diffrn_reflns_av_R_equivalents 0.0302 _diffrn_reflns_av_sigmaI/netI 0.0291 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 29.76 _reflns_number_total 3355 _reflns_number_gt 2619 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0223P)^2^+1.5865P] 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 3355 _refine_ls_number_parameters 128 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0424 _refine_ls_R_factor_gt 0.0286 _refine_ls_wR_factor_ref 0.0626 _refine_ls_wR_factor_gt 0.0597 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _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 I1 I 0.22131(3) 0.161396(11) 0.278748(15) 0.02860(7) Uani 1 1 d . . . N1 N 0.9936(3) 0.23448(14) 0.54818(18) 0.0248(5) Uani 1 1 d . . . N2 N 0.6686(4) 0.20451(17) 0.4636(2) 0.0439(7) Uani 1 1 d . . . H2 H 0.5632 0.2194 0.4136 0.053 Uiso 1 1 calc R . . C1 C 0.8263(4) 0.25691(17) 0.4804(2) 0.0259(6) Uani 1 1 d . . . C2 C 1.0208(5) 0.14787(19) 0.5971(3) 0.0346(7) Uani 1 1 d . . . H2A H 1.0260 0.1513 0.6819 0.042 Uiso 1 1 calc R . . H2B H 1.1526 0.1242 0.5800 0.042 Uiso 1 1 calc R . . C3 C 0.8543(7) 0.0895(3) 0.5506(5) 0.0879(18) Uani 1 1 d . . . H3A H 0.8931 0.0630 0.4798 0.105 Uiso 1 1 calc R . . H3B H 0.8473 0.0427 0.6073 0.105 Uiso 1 1 calc R . . C4 C 0.6602(7) 0.1229(3) 0.5242(4) 0.0687(14) Uani 1 1 d . . . H4A H 0.5985 0.1317 0.5959 0.082 Uiso 1 1 calc R . . H4B H 0.5736 0.0818 0.4750 0.082 Uiso 1 1 calc R . . C5 C 1.1596(5) 0.2935(2) 0.5885(3) 0.0363(7) Uani 1 1 d . . . H5A H 1.2819 0.2777 0.5542 0.055 Uiso 1 1 calc R . . H5B H 1.1890 0.2903 0.6726 0.055 Uiso 1 1 calc R . . H5C H 1.1192 0.3523 0.5656 0.055 Uiso 1 1 calc R . . C6 C 0.8041(4) 0.34111(17) 0.4215(2) 0.0248(5) Uani 1 1 d . . . C7 C 0.9529(5) 0.37255(18) 0.3586(2) 0.0304(6) Uani 1 1 d . . . H7 H 1.0740 0.3405 0.3542 0.036 Uiso 1 1 calc R . . C8 C 0.9235(5) 0.45100(19) 0.3025(3) 0.0363(7) Uani 1 1 d . . . H8 H 1.0259 0.4732 0.2607 0.044 Uiso 1 1 calc R . . C9 C 0.7458(5) 0.49693(18) 0.3073(2) 0.0374(7) Uani 1 1 d . . . H9 H 0.7258 0.5502 0.2677 0.045 Uiso 1 1 calc R . . C11 C 0.6273(5) 0.38841(19) 0.4265(2) 0.0316(6) Uani 1 1 d . . . H11 H 0.5259 0.3673 0.4698 0.038 Uiso 1 1 calc R . . C10 C 0.5970(5) 0.46609(19) 0.3691(2) 0.0365(7) Uani 1 1 d . . . H10 H 0.4750 0.4978 0.3722 0.044 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 I1 0.02670(11) 0.02946(10) 0.02925(9) -0.00415(7) 0.00219(7) -0.00233(8) N1 0.0266(12) 0.0249(11) 0.0226(10) 0.0006(8) 0.0019(9) -0.0024(9) N2 0.0417(16) 0.0382(15) 0.0457(15) 0.0205(12) -0.0174(12) -0.0181(12) C1 0.0308(15) 0.0263(14) 0.0204(11) 0.0006(10) 0.0022(11) -0.0033(11) C2 0.0383(18) 0.0318(16) 0.0322(14) 0.0097(12) -0.0012(13) 0.0012(13) C3 0.059(3) 0.041(2) 0.155(5) 0.050(3) -0.018(3) -0.009(2) C4 0.064(3) 0.052(2) 0.080(3) 0.041(2) -0.025(2) -0.032(2) C5 0.0282(16) 0.0418(18) 0.0371(15) -0.0020(13) -0.0027(12) -0.0089(13) C6 0.0306(15) 0.0221(12) 0.0211(11) -0.0008(10) 0.0015(10) -0.0008(11) C7 0.0354(17) 0.0249(14) 0.0318(14) -0.0013(11) 0.0080(12) -0.0012(12) C8 0.052(2) 0.0262(15) 0.0323(15) 0.0001(11) 0.0118(14) -0.0092(14) C9 0.065(2) 0.0186(14) 0.0270(13) -0.0015(10) -0.0006(14) 0.0017(13) C11 0.0355(17) 0.0344(16) 0.0254(13) -0.0016(11) 0.0053(12) 0.0028(13) C10 0.0442(19) 0.0341(16) 0.0296(14) -0.0059(12) -0.0007(13) 0.0137(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 C1 1.320(3) . ? N1 C5 1.461(4) . ? N1 C2 1.467(3) . ? N2 C1 1.317(4) . ? N2 C4 1.460(4) . ? N2 H2 0.8800 . ? C1 C6 1.480(4) . ? C2 C3 1.475(5) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.380(6) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 C11 1.388(4) . ? C6 C7 1.392(4) . ? C7 C8 1.389(4) . ? C7 H7 0.9500 . ? C8 C9 1.382(5) . ? C8 H8 0.9500 . ? C9 C10 1.381(5) . ? C9 H9 0.9500 . ? C11 C10 1.386(4) . ? C11 H11 0.9500 . ? C10 H10 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 N1 C5 124.1(2) . . ? C1 N1 C2 121.9(2) . . ? C5 N1 C2 113.8(2) . . ? C1 N2 C4 123.1(3) . . ? C1 N2 H2 118.4 . . ? C4 N2 H2 118.4 . . ? N2 C1 N1 120.6(3) . . ? N2 C1 C6 116.8(2) . . ? N1 C1 C6 122.6(2) . . ? N1 C2 C3 112.0(3) . . ? N1 C2 H2A 109.2 . . ? C3 C2 H2A 109.2 . . ? N1 C2 H2B 109.2 . . ? C3 C2 H2B 109.2 . . ? H2A C2 H2B 107.9 . . ? C4 C3 C2 118.5(4) . . ? C4 C3 H3A 107.7 . . ? C2 C3 H3A 107.7 . . ? C4 C3 H3B 107.7 . . ? C2 C3 H3B 107.7 . . ? H3A C3 H3B 107.1 . . ? C3 C4 N2 110.1(3) . . ? C3 C4 H4A 109.6 . . ? N2 C4 H4A 109.6 . . ? C3 C4 H4B 109.6 . . ? N2 C4 H4B 109.6 . . ? H4A C4 H4B 108.2 . . ? N1 C5 H5A 109.5 . . ? N1 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N1 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C11 C6 C7 119.5(3) . . ? C11 C6 C1 118.9(3) . . ? C7 C6 C1 121.6(3) . . ? C8 C7 C6 119.7(3) . . ? C8 C7 H7 120.2 . . ? C6 C7 H7 120.2 . . ? C9 C8 C7 120.2(3) . . ? C9 C8 H8 119.9 . . ? C7 C8 H8 119.9 . . ? C10 C9 C8 120.5(3) . . ? C10 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C10 C11 C6 120.8(3) . . ? C10 C11 H11 119.6 . . ? C6 C11 H11 119.6 . . ? C9 C10 C11 119.4(3) . . ? C9 C10 H10 120.3 . . ? C11 C10 H10 120.3 . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 29.76 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 1.387 _refine_diff_density_min -1.289 _refine_diff_density_rms 0.099 # Attachment '- 20.cif' data_e771a _database_code_depnum_ccdc_archive 'CCDC 753163' #TrackingRef '- 20.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H15 N2, F6 P' _chemical_formula_sum 'C11 H15 F6 N2 P' _chemical_formula_weight 320.22 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.4539(12) _cell_length_b 12.1945(7) _cell_length_c 15.6621(12) _cell_angle_alpha 90.00 _cell_angle_beta 113.353(2) _cell_angle_gamma 90.00 _cell_volume 2709.8(3) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2227 _cell_measurement_theta_min 2.87 _cell_measurement_theta_max 21.89 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.570 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1312 _exptl_absorpt_coefficient_mu 0.264 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9690 _exptl_absorpt_correction_T_max 0.9843 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21182 _diffrn_reflns_av_R_equivalents 0.0934 _diffrn_reflns_av_sigmaI/netI 0.2362 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.44 _diffrn_reflns_theta_max 29.16 _reflns_number_total 7374 _reflns_number_gt 3268 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.1386P)^2^+0.5334P] 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 7374 _refine_ls_number_parameters 400 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2109 _refine_ls_R_factor_gt 0.0878 _refine_ls_wR_factor_ref 0.3527 _refine_ls_wR_factor_gt 0.2234 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _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 C1 C 0.2256(3) 0.0257(5) 0.4656(3) 0.0277(11) Uani 1 1 d . . . N1 N 0.2570(3) -0.0330(4) 0.5419(3) 0.0313(10) Uani 1 1 d . . . C2 C 0.3588(3) -0.0415(5) 0.6023(3) 0.0358(14) Uani 1 1 d . . . H2A H 0.3747 -0.1187 0.6217 0.043 Uiso 1 1 calc R . . H2B H 0.3728 0.0032 0.6590 0.043 Uiso 1 1 calc R . . C3 C 0.4184(3) -0.0022(5) 0.5519(3) 0.0389(15) Uani 1 1 d . . . H3A H 0.4176 -0.0578 0.5054 0.047 Uiso 1 1 calc R . . H3B H 0.4844 0.0071 0.5968 0.047 Uiso 1 1 calc R . . C4 C 0.3814(3) 0.1055(5) 0.5036(4) 0.0397(15) Uani 1 1 d . . . H4A H 0.3894 0.1637 0.5502 0.048 Uiso 1 1 calc R . . H4B H 0.4169 0.1272 0.4657 0.048 Uiso 1 1 calc R . . N2 N 0.2817(3) 0.0923(4) 0.4440(3) 0.0325(11) Uani 1 1 d . . . H2 H 0.2579 0.1300 0.3919 0.039 Uiso 1 1 calc R . . C5 C 0.1951(4) -0.0924(5) 0.5771(4) 0.0403(15) Uani 1 1 d . . . H5A H 0.1321 -0.0594 0.5516 0.060 Uiso 1 1 calc R . . H5B H 0.2211 -0.0879 0.6452 0.060 Uiso 1 1 calc R . . H5C H 0.1908 -0.1694 0.5581 0.060 Uiso 1 1 calc R . . C6 C 0.1245(3) 0.0228(5) 0.4003(3) 0.0293(12) Uani 1 1 d . . . C7 C 0.0725(3) 0.1167(5) 0.3795(4) 0.0399(14) Uani 1 1 d . . . H7 H 0.1015 0.1845 0.4049 0.048 Uiso 1 1 calc R . . C8 C -0.0224(4) 0.1139(6) 0.3217(4) 0.0447(16) Uani 1 1 d . . . H8 H -0.0584 0.1796 0.3085 0.054 Uiso 1 1 calc R . . C9 C -0.0639(3) 0.0179(5) 0.2838(3) 0.0375(14) Uani 1 1 d . . . H9 H -0.1289 0.0169 0.2438 0.045 Uiso 1 1 calc R . . C10 C -0.0119(3) -0.0805(5) 0.3032(3) 0.0396(15) Uani 1 1 d . . . H10 H -0.0414 -0.1478 0.2769 0.047 Uiso 1 1 calc R . . C11 C 0.0837(3) -0.0775(5) 0.3616(4) 0.0365(13) Uani 1 1 d . . . H11 H 0.1205 -0.1426 0.3748 0.044 Uiso 1 1 calc R . . C12 C 0.2799(3) 0.5474(5) 0.5773(3) 0.0271(11) Uani 1 1 d . . . N3 N 0.3075(3) 0.4730(4) 0.5325(3) 0.0288(10) Uani 1 1 d . . . C13 C 0.4083(3) 0.4452(5) 0.5597(4) 0.0391(14) Uani 1 1 d . . . H13A H 0.4211 0.4341 0.5032 0.047 Uiso 1 1 calc R . . H13B H 0.4228 0.3759 0.5956 0.047 Uiso 1 1 calc R . . C14 C 0.4698(4) 0.5341(6) 0.6169(4) 0.0537(18) Uani 1 1 d . . . H14A H 0.5358 0.5080 0.6444 0.064 Uiso 1 1 calc R . . H14B H 0.4669 0.5977 0.5766 0.064 Uiso 1 1 calc R . . C15 C 0.4410(4) 0.5690(7) 0.6920(4) 0.057(2) Uani 1 1 d . . . H15A H 0.4515 0.5087 0.7373 0.068 Uiso 1 1 calc R . . H15B H 0.4789 0.6330 0.7251 0.068 Uiso 1 1 calc R . . C16 C 0.2433(4) 0.4001(5) 0.4612(4) 0.0395(14) Uani 1 1 d . . . H16A H 0.1780 0.4192 0.4495 0.059 Uiso 1 1 calc R . . H16B H 0.2555 0.3239 0.4827 0.059 Uiso 1 1 calc R . . H16C H 0.2535 0.4082 0.4036 0.059 Uiso 1 1 calc R . . N4 N 0.3410(3) 0.5981(4) 0.6505(3) 0.0393(12) Uani 1 1 d . . . H4 H 0.3210 0.6517 0.6756 0.047 Uiso 1 1 calc R . . C17 C 0.1798(3) 0.5801(5) 0.5474(3) 0.0277(12) Uani 1 1 d . . . C18 C 0.1280(3) 0.6154(5) 0.4566(3) 0.0314(12) Uani 1 1 d . . . H18 H 0.1559 0.6154 0.4124 0.038 Uiso 1 1 calc R . . C19 C 0.0355(3) 0.6505(5) 0.4307(4) 0.0361(13) Uani 1 1 d . . . H19 H -0.0003 0.6737 0.3687 0.043 Uiso 1 1 calc R . . C20 C -0.0043(3) 0.6515(5) 0.4966(4) 0.0380(14) Uani 1 1 d . . . H20 H -0.0675 0.6754 0.4793 0.046 Uiso 1 1 calc R . . C21 C 0.0471(3) 0.6181(5) 0.5859(4) 0.0370(13) Uani 1 1 d . . . H21 H 0.0189 0.6190 0.6299 0.044 Uiso 1 1 calc R . . C22 C 0.1399(3) 0.5829(5) 0.6134(3) 0.0351(13) Uani 1 1 d . . . H22 H 0.1755 0.5612 0.6759 0.042 Uiso 1 1 calc R . . P1 P 0.33030(8) 0.73532(13) 0.36046(8) 0.0302(4) Uani 1 1 d . . . F1 F 0.3579(3) 0.7111(4) 0.2742(3) 0.0700(13) Uani 1 1 d . . . F2 F 0.3240(3) 0.6073(3) 0.3742(3) 0.0610(11) Uani 1 1 d . . . F3 F 0.4369(2) 0.7367(4) 0.4288(3) 0.0747(15) Uani 1 1 d . . . F4 F 0.3013(3) 0.7591(3) 0.4456(3) 0.0579(11) Uani 1 1 d . . . F5 F 0.3342(3) 0.8645(3) 0.3440(2) 0.0655(12) Uani 1 1 d . . . F6 F 0.2223(3) 0.7336(4) 0.2916(3) 0.0929(18) Uani 1 1 d . . . P2 P 0.28178(10) 0.25461(14) 0.22642(9) 0.0383(4) Uani 1 1 d . . . F7 F 0.2024(3) 0.2380(4) 0.2668(3) 0.0671(13) Uani 1 1 d . . . F8 F 0.3623(3) 0.2722(4) 0.1891(4) 0.0854(16) Uani 1 1 d . . . F9 F 0.3549(10) 0.210(3) 0.3105(15) 0.0854(16) Uani 0.50(3) 1 d P . . F10 F 0.2952(16) 0.3792(16) 0.2590(15) 0.0854(16) Uani 0.50(3) 1 d P . . F11 F 0.1963(11) 0.3071(19) 0.1339(11) 0.088(5) Uani 0.50(3) 1 d P . . F12 F 0.2465(17) 0.1474(18) 0.172(2) 0.0854(16) Uani 0.50(3) 1 d P . . F9A F 0.3080(16) 0.1238(8) 0.2445(19) 0.0854(16) Uani 0.50(3) 1 d P . . F10A F 0.3502(10) 0.2738(17) 0.3334(8) 0.0854(16) Uani 0.50(3) 1 d P . . F11A F 0.261(2) 0.3740(17) 0.216(2) 0.0854(16) Uani 0.50(3) 1 d P . . F12A F 0.2189(11) 0.236(3) 0.1248(8) 0.0854(16) Uani 0.50(3) 1 d P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.025(2) 0.038(4) 0.020(2) -0.006(2) 0.0088(17) -0.003(2) N1 0.0239(18) 0.048(3) 0.0241(19) -0.0009(19) 0.0112(15) -0.0011(18) C2 0.028(2) 0.059(4) 0.020(2) -0.002(2) 0.0101(18) -0.001(2) C3 0.0202(19) 0.073(5) 0.022(2) -0.005(2) 0.0065(17) 0.000(2) C4 0.020(2) 0.065(5) 0.034(3) -0.003(3) 0.0111(19) -0.011(2) N2 0.0243(18) 0.048(3) 0.0251(19) 0.0041(19) 0.0095(16) -0.0033(18) C5 0.042(3) 0.051(5) 0.029(2) 0.008(2) 0.015(2) -0.005(3) C6 0.0200(19) 0.043(4) 0.026(2) 0.000(2) 0.0100(17) 0.001(2) C7 0.026(2) 0.053(4) 0.036(3) -0.007(3) 0.007(2) 0.002(2) C8 0.029(2) 0.066(5) 0.036(3) 0.001(3) 0.009(2) 0.007(3) C9 0.025(2) 0.058(5) 0.028(2) 0.002(3) 0.0083(19) 0.000(2) C10 0.031(2) 0.055(5) 0.030(3) -0.004(2) 0.009(2) -0.012(3) C11 0.028(2) 0.044(4) 0.035(3) 0.000(2) 0.010(2) 0.001(2) C12 0.028(2) 0.032(4) 0.024(2) 0.004(2) 0.0142(18) -0.003(2) N3 0.0252(18) 0.039(3) 0.0258(19) -0.0038(18) 0.0142(16) 0.0008(17) C13 0.028(2) 0.061(5) 0.031(2) 0.002(3) 0.015(2) 0.012(2) C14 0.029(3) 0.074(6) 0.056(4) -0.008(4) 0.014(3) 0.001(3) C15 0.028(2) 0.099(6) 0.034(3) -0.013(3) 0.002(2) 0.001(3) C16 0.034(2) 0.050(4) 0.034(3) -0.011(3) 0.013(2) -0.003(2) N4 0.0264(19) 0.059(4) 0.029(2) -0.018(2) 0.0072(17) 0.001(2) C17 0.0212(19) 0.039(4) 0.026(2) -0.004(2) 0.0122(17) -0.0001(19) C18 0.026(2) 0.042(4) 0.027(2) 0.001(2) 0.0105(19) -0.001(2) C19 0.027(2) 0.037(4) 0.038(3) 0.001(2) 0.007(2) -0.001(2) C20 0.023(2) 0.042(4) 0.050(3) -0.004(3) 0.016(2) 0.003(2) C21 0.033(2) 0.039(4) 0.046(3) -0.011(3) 0.023(2) 0.001(2) C22 0.031(2) 0.047(4) 0.029(2) -0.009(2) 0.014(2) -0.003(2) P1 0.0256(5) 0.0414(11) 0.0230(6) -0.0009(5) 0.0091(4) -0.0029(5) F1 0.113(4) 0.072(3) 0.050(2) -0.018(2) 0.059(2) -0.029(3) F2 0.087(3) 0.050(3) 0.060(2) 0.0017(19) 0.044(2) -0.006(2) F3 0.0230(15) 0.120(4) 0.067(3) -0.019(2) 0.0030(16) 0.0047(19) F4 0.056(2) 0.079(3) 0.056(2) -0.0189(19) 0.0406(19) -0.0155(19) F5 0.112(4) 0.045(3) 0.041(2) -0.0012(17) 0.032(2) -0.007(2) F6 0.044(2) 0.118(5) 0.074(3) -0.029(3) -0.021(2) 0.011(2) P2 0.0369(7) 0.0524(13) 0.0317(7) -0.0059(7) 0.0201(6) -0.0112(7) F7 0.052(2) 0.087(4) 0.078(3) 0.006(2) 0.043(2) -0.004(2) F8 0.076(3) 0.110(4) 0.104(4) -0.008(3) 0.072(3) -0.017(3) F9 0.076(3) 0.110(4) 0.104(4) -0.008(3) 0.072(3) -0.017(3) F10 0.076(3) 0.110(4) 0.104(4) -0.008(3) 0.072(3) -0.017(3) F11 0.076(3) 0.110(4) 0.104(4) -0.008(3) 0.072(3) -0.017(3) F12 0.076(3) 0.110(4) 0.104(4) -0.008(3) 0.072(3) -0.017(3) F9A 0.076(3) 0.110(4) 0.104(4) -0.008(3) 0.072(3) -0.017(3) F10A 0.076(3) 0.110(4) 0.104(4) -0.008(3) 0.072(3) -0.017(3) F11A 0.076(3) 0.110(4) 0.104(4) -0.008(3) 0.072(3) -0.017(3) F12A 0.076(3) 0.110(4) 0.104(4) -0.008(3) 0.072(3) -0.017(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.310(6) . ? C1 N2 1.326(6) . ? C1 C6 1.490(6) . ? N1 C5 1.470(6) . ? N1 C2 1.483(6) . ? C2 C3 1.510(7) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.511(8) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 N2 1.460(6) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? N2 H2 0.8800 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 C7 1.362(8) . ? C6 C11 1.399(8) . ? C7 C8 1.384(7) . ? C7 H7 0.9500 . ? C8 C9 1.354(9) . ? C8 H8 0.9500 . ? C9 C10 1.409(8) . ? C9 H9 0.9500 . ? C10 C11 1.396(6) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 N4 1.316(6) . ? C12 N3 1.317(6) . ? C12 C17 1.482(6) . ? N3 C16 1.465(6) . ? N3 C13 1.483(6) . ? C13 C14 1.485(9) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.475(8) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 N4 1.463(7) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? N4 H4 0.8800 . ? C17 C18 1.395(6) . ? C17 C22 1.399(6) . ? C18 C19 1.390(7) . ? C18 H18 0.9500 . ? C19 C20 1.394(8) . ? C19 H19 0.9500 . ? C20 C21 1.369(8) . ? C20 H20 0.9500 . ? C21 C22 1.391(7) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? P1 F3 1.569(3) . ? P1 F2 1.585(4) . ? P1 F6 1.588(4) . ? P1 F4 1.593(4) . ? P1 F1 1.597(4) . ? P1 F5 1.602(4) . ? P2 F9 1.460(12) . ? P2 F11A 1.485(18) . ? P2 F12A 1.517(10) . ? P2 F12 1.536(13) . ? P2 F8 1.585(4) . ? P2 F10 1.590(16) . ? P2 F7 1.600(4) . ? P2 F10A 1.605(11) . ? P2 F9A 1.642(11) . ? P2 F11 1.655(13) . ? 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 N1 C1 N2 121.6(4) . . ? N1 C1 C6 121.5(4) . . ? N2 C1 C6 116.9(4) . . ? C1 N1 C5 123.4(4) . . ? C1 N1 C2 122.4(4) . . ? C5 N1 C2 114.1(4) . . ? N1 C2 C3 110.9(4) . . ? N1 C2 H2A 109.5 . . ? C3 C2 H2A 109.5 . . ? N1 C2 H2B 109.5 . . ? C3 C2 H2B 109.5 . . ? H2A C2 H2B 108.0 . . ? C2 C3 C4 110.4(4) . . ? C2 C3 H3A 109.6 . . ? C4 C3 H3A 109.6 . . ? C2 C3 H3B 109.6 . . ? C4 C3 H3B 109.6 . . ? H3A C3 H3B 108.1 . . ? N2 C4 C3 108.6(5) . . ? N2 C4 H4A 110.0 . . ? C3 C4 H4A 110.0 . . ? N2 C4 H4B 110.0 . . ? C3 C4 H4B 110.0 . . ? H4A C4 H4B 108.4 . . ? C1 N2 C4 122.4(4) . . ? C1 N2 H2 118.8 . . ? C4 N2 H2 118.8 . . ? C7 C6 C11 120.6(5) . . ? C7 C6 C1 120.2(5) . . ? C11 C6 C1 119.2(5) . . ? C6 C7 C8 120.5(6) . . ? C6 C7 H7 119.8 . . ? C8 C7 H7 119.8 . . ? C9 C8 C7 120.2(6) . . ? C9 C8 H8 119.9 . . ? C7 C8 H8 119.9 . . ? C8 C9 C10 120.7(5) . . ? C8 C9 H9 119.6 . . ? C10 C9 H9 119.6 . . ? C11 C10 C9 118.9(5) . . ? C11 C10 H10 120.5 . . ? C9 C10 H10 120.5 . . ? C10 C11 C6 119.0(5) . . ? C10 C11 H11 120.5 . . ? C6 C11 H11 120.5 . . ? N4 C12 N3 121.0(4) . . ? N4 C12 C17 116.7(4) . . ? N3 C12 C17 122.3(4) . . ? C12 N3 C16 124.1(4) . . ? C12 N3 C13 122.0(4) . . ? C16 N3 C13 113.4(4) . . ? N3 C13 C14 110.8(5) . . ? N3 C13 H13A 109.5 . . ? C14 C13 H13A 109.5 . . ? N3 C13 H13B 109.5 . . ? C14 C13 H13B 109.5 . . ? H13A C13 H13B 108.1 . . ? C15 C14 C13 111.6(5) . . ? C15 C14 H14A 109.3 . . ? C13 C14 H14A 109.3 . . ? C15 C14 H14B 109.3 . . ? C13 C14 H14B 109.3 . . ? H14A C14 H14B 108.0 . . ? N4 C15 C14 108.4(4) . . ? N4 C15 H15A 110.0 . . ? C14 C15 H15A 110.0 . . ? N4 C15 H15B 110.0 . . ? C14 C15 H15B 110.0 . . ? H15A C15 H15B 108.4 . . ? C12 N4 C15 122.7(5) . . ? C12 N4 H4 118.6 . . ? C15 N4 H4 118.6 . . ? C18 C17 C22 120.2(4) . . ? C18 C17 C12 120.7(4) . . ? C22 C17 C12 118.9(4) . . ? C19 C18 C17 120.0(5) . . ? C19 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? C18 C19 C20 119.4(5) . . ? C18 C19 H19 120.3 . . ? C20 C19 H19 120.3 . . ? C21 C20 C19 120.4(5) . . ? C21 C20 H20 119.8 . . ? C19 C20 H20 119.8 . . ? C20 C21 C22 121.1(5) . . ? C20 C21 H21 119.4 . . ? C22 C21 H21 119.4 . . ? C21 C22 C17 118.7(5) . . ? C21 C22 H22 120.6 . . ? C17 C22 H22 120.6 . . ? F3 P1 F2 91.3(2) . . ? F3 P1 F6 179.8(3) . . ? F2 P1 F6 88.5(3) . . ? F3 P1 F4 89.7(2) . . ? F2 P1 F4 90.8(2) . . ? F6 P1 F4 90.1(3) . . ? F3 P1 F1 91.1(2) . . ? F2 P1 F1 89.1(2) . . ? F6 P1 F1 89.1(3) . . ? F4 P1 F1 179.2(2) . . ? F3 P1 F5 90.2(3) . . ? F2 P1 F5 178.4(2) . . ? F6 P1 F5 90.0(3) . . ? F4 P1 F5 89.8(2) . . ? F1 P1 F5 90.4(2) . . ? F9 P2 F11A 121.6(11) . . ? F9 P2 F12A 146.8(10) . . ? F11A P2 F12A 90.3(11) . . ? F9 P2 F12 99.1(11) . . ? F11A P2 F12 139.3(12) . . ? F9 P2 F8 86.8(6) . . ? F11A P2 F8 89.3(8) . . ? F12A P2 F8 84.4(6) . . ? F12 P2 F8 94.0(5) . . ? F9 P2 F10 96.5(12) . . ? F12A P2 F10 115.2(11) . . ? F12 P2 F10 164.4(12) . . ? F8 P2 F10 88.2(7) . . ? F9 P2 F7 92.1(6) . . ? F11A P2 F7 90.5(8) . . ? F12A P2 F7 97.1(6) . . ? F12 P2 F7 87.2(5) . . ? F8 P2 F7 178.5(3) . . ? F10 P2 F7 90.9(7) . . ? F11A P2 F10A 89.9(11) . . ? F12A P2 F10A 178.8(8) . . ? F12 P2 F10A 130.1(11) . . ? F8 P2 F10A 94.4(6) . . ? F7 P2 F10A 84.1(6) . . ? F11A P2 F9A 176.9(12) . . ? F12A P2 F9A 92.9(9) . . ? F8 P2 F9A 91.1(4) . . ? F10 P2 F9A 151.7(11) . . ? F7 P2 F9A 89.1(4) . . ? F10A P2 F9A 86.9(8) . . ? F9 P2 F11 177.5(8) . . ? F12 P2 F11 82.0(10) . . ? F8 P2 F11 95.5(7) . . ? F10 P2 F11 82.5(9) . . ? F7 P2 F11 85.6(7) . . ? F10A P2 F11 145.6(7) . . ? F9A P2 F11 125.7(9) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 29.16 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.741 _refine_diff_density_min -0.835 _refine_diff_density_rms 0.150 # Attachment '- 21.cif' data_e830a _database_code_depnum_ccdc_archive 'CCDC 753164' #TrackingRef '- 21.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H15 N2, C F3 O3 S' _chemical_formula_sum 'C12 H15 F3 N2 O3 S' _chemical_formula_weight 324.32 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 Orthorhombic _symmetry_space_group_name_H-M Pbca _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 11.0219(4) _cell_length_b 15.3857(5) _cell_length_c 16.9442(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2873.39(17) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5535 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 26.24 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.499 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1344 _exptl_absorpt_coefficient_mu 0.270 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9479 _exptl_absorpt_correction_T_max 0.9657 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 56466 _diffrn_reflns_av_R_equivalents 0.0412 _diffrn_reflns_av_sigmaI/netI 0.0288 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.40 _diffrn_reflns_theta_max 30.10 _reflns_number_total 4217 _reflns_number_gt 2950 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0445P)^2^+0.6296P] 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 4217 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0621 _refine_ls_R_factor_gt 0.0364 _refine_ls_wR_factor_ref 0.0963 _refine_ls_wR_factor_gt 0.0885 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _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 S1 S 0.25948(3) 0.15275(2) 0.37012(2) 0.02308(10) Uani 1 1 d . . . O3 O 0.15929(9) 0.10981(7) 0.33165(6) 0.0329(3) Uani 1 1 d . . . O1 O 0.22821(11) 0.23107(7) 0.41132(7) 0.0391(3) Uani 1 1 d . . . O2 O 0.36859(9) 0.15499(7) 0.32430(6) 0.0337(3) Uani 1 1 d . . . C5 C 0.48012(12) -0.06010(9) 0.13515(8) 0.0254(3) Uani 1 1 d . . . H5 H 0.5114 -0.0361 0.0877 0.031 Uiso 1 1 calc R . . C8 C 0.33597(12) 0.06369(9) 0.14223(8) 0.0213(3) Uani 1 1 d . . . C6 C 0.38524(12) -0.01856(8) 0.17464(8) 0.0214(3) Uani 1 1 d . . . C11 C 0.38174(13) 0.20594(10) 0.08408(9) 0.0307(3) Uani 1 1 d . . . H11A H 0.3708 0.2007 0.0263 0.037 Uiso 1 1 calc R . . H11B H 0.4462 0.2493 0.0943 0.037 Uiso 1 1 calc R . . C7 C 0.34197(13) -0.05298(8) 0.24540(8) 0.0248(3) Uani 1 1 d . . . H7 H 0.2787 -0.0243 0.2732 0.030 Uiso 1 1 calc R . . C10 C 0.26425(13) 0.23450(10) 0.12234(10) 0.0320(3) Uani 1 1 d . . . H10A H 0.2775 0.2453 0.1793 0.038 Uiso 1 1 calc R . . H10B H 0.2355 0.2891 0.0978 0.038 Uiso 1 1 calc R . . C1 C 0.29624(14) 0.07849(10) 0.45068(9) 0.0297(3) Uani 1 1 d . . . C12 C 0.12403(13) 0.01345(10) 0.15156(9) 0.0299(3) Uani 1 1 d . . . H12A H 0.1606 -0.0446 0.1525 0.045 Uiso 1 1 calc R . . H12B H 0.0627 0.0161 0.1098 0.045 Uiso 1 1 calc R . . H12C H 0.0857 0.0254 0.2026 0.045 Uiso 1 1 calc R . . C2 C 0.39134(14) -0.12891(9) 0.27502(9) 0.0297(3) Uani 1 1 d . . . H2 H 0.3616 -0.1525 0.3231 0.036 Uiso 1 1 calc R . . C9 C 0.17074(13) 0.16404(10) 0.11149(10) 0.0337(4) Uani 1 1 d . . . H9A H 0.0977 0.1783 0.1430 0.040 Uiso 1 1 calc R . . H9B H 0.1466 0.1613 0.0553 0.040 Uiso 1 1 calc R . . C3 C 0.48392(14) -0.17073(9) 0.23491(9) 0.0322(3) Uani 1 1 d . . . H3 H 0.5170 -0.2232 0.2553 0.039 Uiso 1 1 calc R . . C4 C 0.52854(13) -0.13619(10) 0.16502(9) 0.0306(3) Uani 1 1 d . . . H4 H 0.5923 -0.1648 0.1377 0.037 Uiso 1 1 calc R . . N1 N 0.21817(10) 0.07842(8) 0.13630(7) 0.0236(2) Uani 1 1 d . . . N2 N 0.41588(10) 0.12171(8) 0.11773(7) 0.0258(3) Uani 1 1 d . . . H2A H 0.4935 0.1091 0.1218 0.031 Uiso 1 1 calc R . . F1 F 0.20314(10) 0.07005(7) 0.49994(6) 0.0492(3) Uani 1 1 d . . . F3 F 0.39018(10) 0.10774(7) 0.49241(6) 0.0478(3) Uani 1 1 d . . . F2 F 0.32499(10) -0.00071(6) 0.42530(6) 0.0464(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.02006(16) 0.02380(17) 0.02537(18) 0.00087(13) -0.00083(13) -0.00109(13) O3 0.0200(5) 0.0437(6) 0.0349(6) -0.0071(5) -0.0009(4) -0.0040(4) O1 0.0509(7) 0.0267(6) 0.0397(7) -0.0046(5) -0.0055(5) 0.0084(5) O2 0.0231(5) 0.0425(6) 0.0354(6) 0.0076(5) 0.0043(4) -0.0066(4) C5 0.0204(6) 0.0291(7) 0.0268(7) -0.0015(6) -0.0012(6) 0.0007(5) C8 0.0183(6) 0.0256(7) 0.0200(6) -0.0029(5) -0.0002(5) 0.0020(5) C6 0.0172(6) 0.0220(6) 0.0250(7) -0.0021(5) -0.0029(5) -0.0010(5) C11 0.0293(7) 0.0283(7) 0.0346(8) 0.0105(6) 0.0000(6) 0.0016(6) C7 0.0230(6) 0.0246(7) 0.0267(7) -0.0032(6) 0.0010(6) -0.0013(5) C10 0.0283(7) 0.0270(8) 0.0408(9) 0.0059(6) -0.0004(7) 0.0051(6) C1 0.0333(8) 0.0294(8) 0.0263(8) 0.0005(6) 0.0044(6) 0.0031(6) C12 0.0176(6) 0.0340(8) 0.0382(8) -0.0060(6) -0.0003(6) -0.0039(6) C2 0.0360(8) 0.0246(7) 0.0284(7) 0.0014(6) -0.0027(6) -0.0043(6) C9 0.0227(7) 0.0333(8) 0.0453(9) 0.0033(7) -0.0042(6) 0.0081(6) C3 0.0349(8) 0.0226(7) 0.0391(9) -0.0023(6) -0.0110(7) 0.0033(6) C4 0.0249(7) 0.0294(8) 0.0375(9) -0.0076(6) -0.0027(6) 0.0059(6) N1 0.0170(5) 0.0257(6) 0.0283(6) -0.0006(5) 0.0003(5) 0.0016(4) N2 0.0168(5) 0.0287(6) 0.0319(7) 0.0065(5) 0.0007(5) 0.0025(5) F1 0.0545(6) 0.0560(6) 0.0372(6) 0.0115(5) 0.0214(5) 0.0014(5) F3 0.0495(6) 0.0569(7) 0.0369(5) 0.0032(4) -0.0168(5) 0.0041(5) F2 0.0703(7) 0.0281(5) 0.0407(6) 0.0032(4) 0.0064(5) 0.0126(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O2 1.4318(10) . ? S1 O1 1.4347(11) . ? S1 O3 1.4426(10) . ? S1 C1 1.8255(15) . ? C5 C4 1.383(2) . ? C5 C6 1.3963(19) . ? C5 H5 0.9500 . ? C8 N2 1.3210(17) . ? C8 N1 1.3218(17) . ? C8 C6 1.4825(19) . ? C6 C7 1.395(2) . ? C11 N2 1.4651(18) . ? C11 C10 1.513(2) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C7 C2 1.383(2) . ? C7 H7 0.9500 . ? C10 C9 1.507(2) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C1 F1 1.3291(17) . ? C1 F2 1.3305(17) . ? C1 F3 1.3320(18) . ? C12 N1 1.4639(18) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C2 C3 1.385(2) . ? C2 H2 0.9500 . ? C9 N1 1.4783(19) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C3 C4 1.388(2) . ? C3 H3 0.9500 . ? C4 H4 0.9500 . ? N2 H2A 0.8800 . ? 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 O2 S1 O1 116.45(7) . . ? O2 S1 O3 114.14(6) . . ? O1 S1 O3 114.87(7) . . ? O2 S1 C1 103.54(7) . . ? O1 S1 C1 102.42(7) . . ? O3 S1 C1 102.78(7) . . ? C4 C5 C6 120.09(14) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? N2 C8 N1 121.01(12) . . ? N2 C8 C6 116.67(11) . . ? N1 C8 C6 122.30(12) . . ? C7 C6 C5 119.61(12) . . ? C7 C6 C8 121.15(12) . . ? C5 C6 C8 119.18(12) . . ? N2 C11 C10 108.05(12) . . ? N2 C11 H11A 110.1 . . ? C10 C11 H11A 110.1 . . ? N2 C11 H11B 110.1 . . ? C10 C11 H11B 110.1 . . ? H11A C11 H11B 108.4 . . ? C2 C7 C6 119.88(13) . . ? C2 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C9 C10 C11 108.91(13) . . ? C9 C10 H10A 109.9 . . ? C11 C10 H10A 109.9 . . ? C9 C10 H10B 109.9 . . ? C11 C10 H10B 109.9 . . ? H10A C10 H10B 108.3 . . ? F1 C1 F2 107.29(12) . . ? F1 C1 F3 107.44(12) . . ? F2 C1 F3 107.21(13) . . ? F1 C1 S1 111.06(11) . . ? F2 C1 S1 112.60(10) . . ? F3 C1 S1 110.98(10) . . ? N1 C12 H12A 109.5 . . ? N1 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N1 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C7 C2 C3 120.29(14) . . ? C7 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? N1 C9 C10 111.37(12) . . ? N1 C9 H9A 109.4 . . ? C10 C9 H9A 109.4 . . ? N1 C9 H9B 109.4 . . ? C10 C9 H9B 109.4 . . ? H9A C9 H9B 108.0 . . ? C2 C3 C4 120.13(14) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C5 C4 C3 119.98(14) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C8 N1 C12 124.45(12) . . ? C8 N1 C9 121.45(12) . . ? C12 N1 C9 114.09(11) . . ? C8 N2 C11 123.28(11) . . ? C8 N2 H2A 118.4 . . ? C11 N2 H2A 118.4 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.10 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.278 _refine_diff_density_min -0.367 _refine_diff_density_rms 0.054 # Attachment '- 23.cif' data_e488a _database_code_depnum_ccdc_archive 'CCDC 753165' #TrackingRef '- 23.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H24 N4, 4(H2 O), 2(Cl)' _chemical_formula_sum 'C16 H32 Cl2 N4 O4' _chemical_formula_weight 415.36 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' Cl Cl 0.1484 0.1585 '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 P2(1)/n _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.8040(3) _cell_length_b 9.3589(2) _cell_length_c 11.3818(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.5590(10) _cell_angle_gamma 90.00 _cell_volume 1039.42(5) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4591 _cell_measurement_theta_min 2.62 _cell_measurement_theta_max 27.45 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.327 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 444 _exptl_absorpt_coefficient_mu 0.340 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9320 _exptl_absorpt_correction_T_max 0.9603 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12120 _diffrn_reflns_av_R_equivalents 0.0341 _diffrn_reflns_av_sigmaI/netI 0.0260 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.62 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2388 _reflns_number_gt 2029 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0492P)^2^+1.3652P] 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 2388 _refine_ls_number_parameters 133 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0538 _refine_ls_R_factor_gt 0.0452 _refine_ls_wR_factor_ref 0.1248 _refine_ls_wR_factor_gt 0.1184 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.059 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.74899(19) 0.6397(2) 0.09063(15) 0.0166(4) Uani 1 1 d . . . N1 N 0.75446(17) 0.77717(17) 0.11463(14) 0.0191(3) Uani 1 1 d . . . C2 C 0.8786(2) 0.8416(2) 0.1763(2) 0.0283(5) Uani 1 1 d . . . H2A H 0.8520 0.9171 0.2306 0.034 Uiso 1 1 calc R . . H2B H 0.9338 0.8865 0.1180 0.034 Uiso 1 1 calc R . . C3 C 0.9637(2) 0.7302(2) 0.24561(19) 0.0267(5) Uani 1 1 d . . . H3A H 0.9148 0.6960 0.3123 0.032 Uiso 1 1 calc R . . H3B H 1.0520 0.7723 0.2782 0.032 Uiso 1 1 calc R . . C4 C 0.9896(2) 0.6068(2) 0.16517(19) 0.0246(4) Uani 1 1 d . . . H4A H 1.0470 0.6385 0.1032 0.029 Uiso 1 1 calc R . . H4B H 1.0384 0.5292 0.2109 0.029 Uiso 1 1 calc R . . N2 N 0.85666(17) 0.55512(18) 0.11112(15) 0.0207(4) Uani 1 1 d . . . H2 H 0.8483 0.4643 0.0916 0.025 Uiso 1 1 calc R . . C5 C 0.6428(2) 0.8770(2) 0.0789(2) 0.0267(5) Uani 1 1 d . . . H5A H 0.5851 0.8372 0.0117 0.040 Uiso 1 1 calc R . . H5B H 0.6813 0.9684 0.0562 0.040 Uiso 1 1 calc R . . H5C H 0.5874 0.8921 0.1451 0.040 Uiso 1 1 calc R . . C6 C 0.61918(19) 0.57072(19) 0.04187(16) 0.0160(4) Uani 1 1 d . . . C7 C 0.5019(2) 0.5840(2) 0.10138(16) 0.0183(4) Uani 1 1 d . . . H7 H 0.5039 0.6411 0.1706 0.022 Uiso 1 1 calc R . . C8 C 0.61745(19) 0.4861(2) -0.05934(16) 0.0185(4) Uani 1 1 d . . . H8 H 0.6977 0.4766 -0.0992 0.022 Uiso 1 1 calc R . . Cl1 Cl 0.86210(6) 0.22271(6) 0.09477(5) 0.03218(18) Uani 1 1 d . . . O1 O 0.67774(19) 0.3050(2) 0.66297(15) 0.0338(4) Uani 1 1 d D . . O2 O 0.7366(2) 0.0996(2) 0.84702(17) 0.0427(5) Uani 1 1 d D . . H10 H 0.756(3) 0.139(3) 0.9048(19) 0.035(6) Uiso 1 1 d D . . H11 H 0.725(3) 0.156(3) 0.801(2) 0.035(6) Uiso 1 1 d D . . H12 H 0.703(3) 0.3845(14) 0.664(2) 0.033(5) Uiso 1 1 d D . . H13 H 0.5994(12) 0.302(3) 0.642(2) 0.033(5) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0177(9) 0.0191(9) 0.0132(8) 0.0001(6) 0.0024(7) -0.0017(7) N1 0.0199(8) 0.0184(8) 0.0189(8) -0.0016(6) 0.0007(6) -0.0013(6) C2 0.0249(11) 0.0241(10) 0.0352(11) -0.0084(9) 0.0000(9) -0.0073(8) C3 0.0193(10) 0.0362(12) 0.0240(10) -0.0041(8) -0.0017(8) -0.0076(8) C4 0.0143(9) 0.0300(11) 0.0287(10) 0.0016(8) -0.0012(8) -0.0022(8) N2 0.0171(8) 0.0188(8) 0.0255(8) -0.0021(6) -0.0011(6) -0.0010(6) C5 0.0289(11) 0.0180(9) 0.0330(11) 0.0006(8) 0.0017(9) 0.0038(8) C6 0.0165(9) 0.0154(8) 0.0155(8) 0.0012(6) -0.0009(7) 0.0008(6) C7 0.0201(9) 0.0195(9) 0.0151(8) -0.0028(7) 0.0012(7) 0.0011(7) C8 0.0180(9) 0.0211(9) 0.0167(8) -0.0004(7) 0.0028(7) 0.0018(7) Cl1 0.0371(3) 0.0266(3) 0.0323(3) 0.0015(2) 0.0005(2) -0.0012(2) O1 0.0372(10) 0.0385(9) 0.0273(8) 0.0028(7) 0.0110(7) 0.0009(8) O2 0.0492(12) 0.0409(11) 0.0363(10) 0.0057(8) -0.0039(9) -0.0074(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.315(2) . ? C1 N2 1.322(2) . ? C1 C6 1.486(2) . ? N1 C5 1.466(3) . ? N1 C2 1.474(3) . ? C2 C3 1.509(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.510(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 N2 1.468(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? N2 H2 0.8800 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 C7 1.395(3) . ? C6 C8 1.397(3) . ? C7 C8 1.386(3) 3_665 ? C7 H7 0.9500 . ? C8 C7 1.386(3) 3_665 ? C8 H8 0.9500 . ? O1 H12 0.784(10) . ? O1 H13 0.782(10) . ? O2 H10 0.761(17) . ? O2 H11 0.741(17) . ? 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 N1 C1 N2 122.23(17) . . ? N1 C1 C6 121.25(17) . . ? N2 C1 C6 116.49(16) . . ? C1 N1 C5 123.46(17) . . ? C1 N1 C2 120.95(17) . . ? C5 N1 C2 115.54(16) . . ? N1 C2 C3 110.82(17) . . ? N1 C2 H2A 109.5 . . ? C3 C2 H2A 109.5 . . ? N1 C2 H2B 109.5 . . ? C3 C2 H2B 109.5 . . ? H2A C2 H2B 108.1 . . ? C2 C3 C4 109.17(17) . . ? C2 C3 H3A 109.8 . . ? C4 C3 H3A 109.8 . . ? C2 C3 H3B 109.8 . . ? C4 C3 H3B 109.8 . . ? H3A C3 H3B 108.3 . . ? N2 C4 C3 108.17(16) . . ? N2 C4 H4A 110.1 . . ? C3 C4 H4A 110.1 . . ? N2 C4 H4B 110.1 . . ? C3 C4 H4B 110.1 . . ? H4A C4 H4B 108.4 . . ? C1 N2 C4 122.53(17) . . ? C1 N2 H2 118.7 . . ? C4 N2 H2 118.7 . . ? N1 C5 H5A 109.5 . . ? N1 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N1 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C7 C6 C8 120.42(17) . . ? C7 C6 C1 119.74(16) . . ? C8 C6 C1 119.74(17) . . ? C8 C7 C6 119.87(17) 3_665 . ? C8 C7 H7 120.1 3_665 . ? C6 C7 H7 120.1 . . ? C7 C8 C6 119.71(18) 3_665 . ? C7 C8 H8 120.1 3_665 . ? C6 C8 H8 120.1 . . ? H12 O1 H13 110(3) . . ? H10 O2 H11 106(3) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.490 _refine_diff_density_min -0.442 _refine_diff_density_rms 0.068 # Attachment '- 26.cif' data_e999a _database_code_depnum_ccdc_archive 'CCDC 753166' #TrackingRef '- 26.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H19 N2, F6 P' _chemical_formula_sum 'C13 H19 F6 N2 P' _chemical_formula_weight 348.27 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 15.8396(12) _cell_length_b 7.3779(6) _cell_length_c 26.074(2) _cell_angle_alpha 90.00 _cell_angle_beta 92.798(2) _cell_angle_gamma 90.00 _cell_volume 3043.4(4) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1197 _cell_measurement_theta_min 3.05 _cell_measurement_theta_max 27.30 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.520 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1440 _exptl_absorpt_coefficient_mu 0.242 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9716 _exptl_absorpt_correction_T_max 0.9880 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12587 _diffrn_reflns_av_R_equivalents 0.0294 _diffrn_reflns_av_sigmaI/netI 0.0307 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 2.95 _diffrn_reflns_theta_max 27.57 _reflns_number_total 3523 _reflns_number_gt 2554 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.1160P)^2^+1.8186P] 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 3523 _refine_ls_number_parameters 201 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0759 _refine_ls_R_factor_gt 0.0523 _refine_ls_wR_factor_ref 0.1791 _refine_ls_wR_factor_gt 0.1585 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.36177(13) 0.3787(3) 0.11421(8) 0.0245(4) Uani 1 1 d . . . N1 N 0.38446(12) 0.5511(3) 0.11556(7) 0.0273(4) Uani 1 1 d . . . C2 C 0.39684(17) 0.6185(4) 0.06342(9) 0.0360(6) Uani 1 1 d . . . H2A H 0.4544 0.6689 0.0606 0.043 Uiso 1 1 calc R . . H2B H 0.3547 0.7130 0.0535 0.043 Uiso 1 1 calc R . . C3 C 0.38422(17) 0.4491(4) 0.03014(10) 0.0358(6) Uani 1 1 d . . . H3A H 0.3392 0.4678 0.0029 0.043 Uiso 1 1 calc R . . H3B H 0.4372 0.4143 0.0141 0.043 Uiso 1 1 calc R . . N2 N 0.35926(12) 0.3117(3) 0.06739(7) 0.0287(4) Uani 1 1 d . . . C4 C 0.37537(15) 0.6804(3) 0.15720(10) 0.0313(5) Uani 1 1 d . . . H4A H 0.3651 0.6138 0.1893 0.038 Uiso 1 1 calc R . . H4B H 0.3257 0.7588 0.1491 0.038 Uiso 1 1 calc R . . C5 C 0.45402(16) 0.7988(3) 0.16556(11) 0.0376(6) Uani 1 1 d . . . H5A H 0.4609 0.8728 0.1344 0.045 Uiso 1 1 calc R . . H5B H 0.4450 0.8829 0.1944 0.045 Uiso 1 1 calc R . . C6 C 0.53495(17) 0.6940(4) 0.17721(12) 0.0423(6) Uani 1 1 d . . . H6A H 0.5290 0.6203 0.2081 0.063 Uiso 1 1 calc R . . H6B H 0.5820 0.7790 0.1829 0.063 Uiso 1 1 calc R . . H6C H 0.5462 0.6148 0.1481 0.063 Uiso 1 1 calc R . . C7 C 0.35520(17) 0.1220(4) 0.05189(10) 0.0370(6) Uani 1 1 d . . . H7A H 0.4105 0.0836 0.0406 0.055 Uiso 1 1 calc R . . H7B H 0.3127 0.1074 0.0236 0.055 Uiso 1 1 calc R . . H7C H 0.3397 0.0474 0.0811 0.055 Uiso 1 1 calc R . . C8 C 0.34043(13) 0.2730(3) 0.15991(8) 0.0240(4) Uani 1 1 d . . . C9 C 0.39516(14) 0.2702(3) 0.20362(8) 0.0276(5) Uani 1 1 d . . . H9 H 0.4467 0.3362 0.2040 0.033 Uiso 1 1 calc R . . C10 C 0.37441(16) 0.1716(3) 0.24617(9) 0.0319(5) Uani 1 1 d . . . H10 H 0.4109 0.1724 0.2762 0.038 Uiso 1 1 calc R . . C11 C 0.30008(15) 0.0709(3) 0.24515(9) 0.0332(5) Uani 1 1 d . . . H11 H 0.2862 0.0018 0.2743 0.040 Uiso 1 1 calc R . . C12 C 0.24643(15) 0.0714(3) 0.20173(10) 0.0328(5) Uani 1 1 d . . . H12 H 0.1959 0.0019 0.2011 0.039 Uiso 1 1 calc R . . C13 C 0.26579(15) 0.1726(3) 0.15908(9) 0.0290(5) Uani 1 1 d . . . H13 H 0.2284 0.1735 0.1295 0.035 Uiso 1 1 calc R . . P1 P 0.87803(4) 0.66341(9) 0.41458(2) 0.0314(2) Uani 1 1 d . . . F1 F 0.95234(12) 0.6935(3) 0.37682(7) 0.0615(5) Uani 1 1 d . . . F2 F 0.91643(16) 0.4689(3) 0.42766(9) 0.0827(7) Uani 1 1 d . . . F3 F 0.82208(14) 0.5785(4) 0.36908(9) 0.0886(8) Uani 1 1 d . . . F4 F 0.80409(13) 0.6315(4) 0.45275(8) 0.0789(7) Uani 1 1 d . . . F5 F 0.83926(18) 0.8531(3) 0.40160(11) 0.0926(9) Uani 1 1 d . . . F6 F 0.93396(14) 0.7403(4) 0.46066(9) 0.0969(10) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0212(9) 0.0250(10) 0.0275(11) 0.0018(9) 0.0033(8) 0.0011(8) N1 0.0276(9) 0.0246(9) 0.0300(10) 0.0022(8) 0.0047(7) -0.0006(7) C2 0.0411(13) 0.0335(13) 0.0337(13) 0.0101(10) 0.0059(10) -0.0031(10) C3 0.0394(13) 0.0403(14) 0.0283(12) 0.0102(10) 0.0063(10) -0.0001(11) N2 0.0329(10) 0.0291(10) 0.0243(9) 0.0004(8) 0.0040(7) -0.0009(8) C4 0.0292(11) 0.0230(11) 0.0423(14) -0.0036(10) 0.0079(10) 0.0028(8) C5 0.0358(13) 0.0256(12) 0.0519(16) -0.0063(11) 0.0059(11) -0.0031(10) C6 0.0343(13) 0.0434(15) 0.0490(16) -0.0059(12) 0.0005(11) -0.0044(11) C7 0.0452(14) 0.0334(13) 0.0324(13) -0.0068(10) 0.0034(11) -0.0016(11) C8 0.0260(10) 0.0205(10) 0.0259(11) 0.0008(8) 0.0051(8) 0.0019(8) C9 0.0284(10) 0.0260(11) 0.0284(11) -0.0010(9) 0.0013(9) -0.0005(9) C10 0.0359(12) 0.0345(13) 0.0254(11) -0.0007(9) 0.0026(9) 0.0044(10) C11 0.0385(13) 0.0310(12) 0.0309(12) 0.0045(10) 0.0114(10) 0.0032(10) C12 0.0289(11) 0.0285(12) 0.0415(14) 0.0054(10) 0.0081(10) -0.0023(9) C13 0.0294(11) 0.0264(11) 0.0315(12) 0.0000(9) 0.0036(9) -0.0010(9) P1 0.0293(3) 0.0401(4) 0.0249(3) -0.0002(2) 0.0019(2) 0.0024(2) F1 0.0517(11) 0.0786(14) 0.0561(11) 0.0068(10) 0.0222(9) -0.0061(9) F2 0.1025(17) 0.0637(13) 0.0846(16) 0.0247(12) 0.0323(13) 0.0361(13) F3 0.0627(13) 0.135(2) 0.0661(14) -0.0352(15) -0.0128(11) -0.0192(14) F4 0.0530(11) 0.123(2) 0.0633(13) 0.0277(13) 0.0300(10) 0.0171(12) F5 0.108(2) 0.0586(14) 0.113(2) 0.0304(13) 0.0285(16) 0.0377(13) F6 0.0607(13) 0.158(3) 0.0704(14) -0.0681(17) -0.0170(11) 0.0116(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N2 1.316(3) . ? C1 N1 1.322(3) . ? C1 C8 1.477(3) . ? N1 C4 1.458(3) . ? N1 C2 1.470(3) . ? C2 C3 1.530(4) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 N2 1.471(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? N2 C7 1.458(3) . ? C4 C5 1.528(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.515(4) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C13 1.394(3) . ? C8 C9 1.398(3) . ? C9 C10 1.380(3) . ? C9 H9 0.9500 . ? C10 C11 1.391(3) . ? C10 H10 0.9500 . ? C11 C12 1.382(3) . ? C11 H11 0.9500 . ? C12 C13 1.386(3) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? P1 F5 1.559(2) . ? P1 F6 1.564(2) . ? P1 F3 1.576(2) . ? P1 F1 1.5865(17) . ? P1 F2 1.589(2) . ? P1 F4 1.5910(19) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 C1 N1 112.45(19) . . ? N2 C1 C8 123.6(2) . . ? N1 C1 C8 124.0(2) . . ? C1 N1 C4 127.82(19) . . ? C1 N1 C2 110.46(19) . . ? C4 N1 C2 119.32(19) . . ? N1 C2 C3 103.20(19) . . ? N1 C2 H2A 111.1 . . ? C3 C2 H2A 111.1 . . ? N1 C2 H2B 111.1 . . ? C3 C2 H2B 111.1 . . ? H2A C2 H2B 109.1 . . ? N2 C3 C2 102.73(19) . . ? N2 C3 H3A 111.2 . . ? C2 C3 H3A 111.2 . . ? N2 C3 H3B 111.2 . . ? C2 C3 H3B 111.2 . . ? H3A C3 H3B 109.1 . . ? C1 N2 C7 128.1(2) . . ? C1 N2 C3 110.93(19) . . ? C7 N2 C3 119.2(2) . . ? N1 C4 C5 111.76(19) . . ? N1 C4 H4A 109.3 . . ? C5 C4 H4A 109.3 . . ? N1 C4 H4B 109.3 . . ? C5 C4 H4B 109.3 . . ? H4A C4 H4B 107.9 . . ? C6 C5 C4 114.4(2) . . ? C6 C5 H5A 108.7 . . ? C4 C5 H5A 108.7 . . ? C6 C5 H5B 108.7 . . ? C4 C5 H5B 108.7 . . ? H5A C5 H5B 107.6 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N2 C7 H7A 109.5 . . ? N2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C13 C8 C9 119.8(2) . . ? C13 C8 C1 119.7(2) . . ? C9 C8 C1 120.55(19) . . ? C10 C9 C8 120.0(2) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C9 C10 C11 120.0(2) . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? C12 C11 C10 120.0(2) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C11 C12 C13 120.5(2) . . ? C11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? C12 C13 C8 119.6(2) . . ? C12 C13 H13 120.2 . . ? C8 C13 H13 120.2 . . ? F5 P1 F6 92.49(16) . . ? F5 P1 F3 89.56(17) . . ? F6 P1 F3 177.81(16) . . ? F5 P1 F1 92.06(13) . . ? F6 P1 F1 90.94(12) . . ? F3 P1 F1 89.74(12) . . ? F5 P1 F2 179.28(16) . . ? F6 P1 F2 88.07(15) . . ? F3 P1 F2 89.87(16) . . ? F1 P1 F2 88.38(12) . . ? F5 P1 F4 88.53(13) . . ? F6 P1 F4 88.85(14) . . ? F3 P1 F4 90.45(13) . . ? F1 P1 F4 179.38(12) . . ? F2 P1 F4 91.03(13) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.57 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.615 _refine_diff_density_min -0.476 _refine_diff_density_rms 0.064 # Attachment '- 34.cif' data_e755a _database_code_depnum_ccdc_archive 'CCDC 753167' #TrackingRef '- 34.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H20 B, C14 H21 N2' _chemical_formula_sum 'C38 H41 B N2' _chemical_formula_weight 536.54 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' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pna2(1) _symmetry_space_group_name_Hall 'P 2c -2n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 18.620(3) _cell_length_b 16.793(2) _cell_length_c 9.9862(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3122.5(7) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5269 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 23.93 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.141 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152 _exptl_absorpt_coefficient_mu 0.065 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9871 _exptl_absorpt_correction_T_max 0.9948 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 32310 _diffrn_reflns_av_R_equivalents 0.0452 _diffrn_reflns_av_sigmaI/netI 0.0374 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 27.51 _reflns_number_total 6364 _reflns_number_gt 5087 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0409P)^2^+0.1768P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.011(2) _refine_ls_number_reflns 6364 _refine_ls_number_parameters 372 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0539 _refine_ls_R_factor_gt 0.0357 _refine_ls_wR_factor_ref 0.0843 _refine_ls_wR_factor_gt 0.0773 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.013 _refine_ls_shift/su_max 0.010 _refine_ls_shift/su_mean 0.010 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.18451(9) 0.85592(9) 0.57225(16) 0.0300(4) Uani 1 1 d . . . N1 N 0.13350(7) 0.89017(8) 0.64465(14) 0.0340(3) Uani 1 1 d . . . C2 C 0.14759(10) 0.96089(10) 0.7275(2) 0.0490(5) Uani 1 1 d . . . H2A H 0.1186 0.9581 0.8105 0.059 Uiso 1 1 calc R . . H2B H 0.1333 1.0094 0.6779 0.059 Uiso 1 1 calc R . . C3 C 0.22590(10) 0.96532(10) 0.76250(18) 0.0420(4) Uani 1 1 d . . . H3A H 0.2385 0.9215 0.8245 0.050 Uiso 1 1 calc R . . H3B H 0.2362 1.0165 0.8079 0.050 Uiso 1 1 calc R . . C4 C 0.26991(11) 0.95881(10) 0.6373(2) 0.0490(5) Uani 1 1 d . . . H4A H 0.2623 1.0067 0.5813 0.059 Uiso 1 1 calc R . . H4B H 0.3215 0.9561 0.6610 0.059 Uiso 1 1 calc R . . N2 N 0.24949(7) 0.88693(7) 0.56102(15) 0.0362(3) Uani 1 1 d . . . C5 C 0.05985(9) 0.85964(10) 0.6513(2) 0.0409(4) Uani 1 1 d . . . H5A H 0.0513 0.8236 0.5758 0.061 Uiso 1 1 calc R . . H5B H 0.0260 0.9042 0.6469 0.061 Uiso 1 1 calc R . . H5C H 0.0530 0.8307 0.7355 0.061 Uiso 1 1 calc R . . C6 C 0.30791(9) 0.84758(11) 0.4860(2) 0.0425(4) Uani 1 1 d . . . H6A H 0.2889 0.7987 0.4433 0.051 Uiso 1 1 calc R . . H6B H 0.3461 0.8315 0.5494 0.051 Uiso 1 1 calc R . . C7 C 0.34011(11) 0.90086(11) 0.3791(2) 0.0546(5) Uani 1 1 d . . . H7A H 0.3584 0.9500 0.4219 0.066 Uiso 1 1 calc R . . H7B H 0.3814 0.8731 0.3377 0.066 Uiso 1 1 calc R . . C8 C 0.28777(13) 0.92341(12) 0.2712(2) 0.0635(6) Uani 1 1 d . . . H8A H 0.2708 0.8752 0.2258 0.095 Uiso 1 1 calc R . . H8B H 0.3115 0.9583 0.2062 0.095 Uiso 1 1 calc R . . H8C H 0.2469 0.9514 0.3111 0.095 Uiso 1 1 calc R . . C9 C 0.16771(8) 0.77880(9) 0.50556(16) 0.0293(3) Uani 1 1 d . . . C10 C 0.15110(8) 0.77458(9) 0.37013(17) 0.0342(4) Uani 1 1 d . . . H10 H 0.1508 0.8215 0.3170 0.041 Uiso 1 1 calc R . . C11 C 0.13498(9) 0.70147(10) 0.31280(18) 0.0395(4) Uani 1 1 d . . . H11 H 0.1237 0.6982 0.2202 0.047 Uiso 1 1 calc R . . C12 C 0.13534(9) 0.63365(10) 0.3904(2) 0.0413(4) Uani 1 1 d . . . H12 H 0.1239 0.5837 0.3512 0.050 Uiso 1 1 calc R . . C13 C 0.15224(10) 0.63788(10) 0.52482(19) 0.0420(4) Uani 1 1 d . . . H13 H 0.1528 0.5908 0.5775 0.050 Uiso 1 1 calc R . . C14 C 0.16835(9) 0.71041(9) 0.58309(17) 0.0358(4) Uani 1 1 d . . . H14 H 0.1798 0.7133 0.6757 0.043 Uiso 1 1 calc R . . B1 B 0.14880(10) 0.19825(10) 0.44727(18) 0.0275(4) Uani 1 1 d . . . C15 C 0.23675(8) 0.20639(9) 0.43465(15) 0.0291(3) Uani 1 1 d . . . C16 C 0.28142(8) 0.14053(10) 0.41317(16) 0.0329(4) Uani 1 1 d . . . H16 H 0.2597 0.0904 0.3962 0.039 Uiso 1 1 calc R . . C17 C 0.35602(9) 0.14486(11) 0.41539(17) 0.0382(4) Uani 1 1 d . . . H17 H 0.3839 0.0983 0.4006 0.046 Uiso 1 1 calc R . . C18 C 0.38965(9) 0.21687(11) 0.43902(17) 0.0394(4) Uani 1 1 d . . . H18 H 0.4406 0.2206 0.4397 0.047 Uiso 1 1 calc R . . C19 C 0.34787(10) 0.28282(11) 0.46152(18) 0.0413(4) Uani 1 1 d . . . H19 H 0.3702 0.3327 0.4788 0.050 Uiso 1 1 calc R . . C20 C 0.27303(9) 0.27765(10) 0.45943(17) 0.0349(4) Uani 1 1 d . . . H20 H 0.2457 0.3245 0.4755 0.042 Uiso 1 1 calc R . . C21 C 0.12124(8) 0.11849(9) 0.36614(16) 0.0305(3) Uani 1 1 d . . . C22 C 0.14504(9) 0.10163(9) 0.23582(17) 0.0347(4) Uani 1 1 d . . . H22 H 0.1774 0.1377 0.1942 0.042 Uiso 1 1 calc R . . C23 C 0.12345(10) 0.03456(10) 0.16479(19) 0.0414(4) Uani 1 1 d . . . H23 H 0.1414 0.0256 0.0770 0.050 Uiso 1 1 calc R . . C24 C 0.07635(10) -0.01885(10) 0.2209(2) 0.0438(5) Uani 1 1 d . . . H24 H 0.0615 -0.0648 0.1728 0.053 Uiso 1 1 calc R . . C25 C 0.05095(10) -0.00445(10) 0.34847(19) 0.0441(4) Uani 1 1 d . . . H25 H 0.0182 -0.0407 0.3886 0.053 Uiso 1 1 calc R . . C26 C 0.07298(9) 0.06269(10) 0.41856(17) 0.0367(4) Uani 1 1 d . . . H26 H 0.0545 0.0711 0.5061 0.044 Uiso 1 1 calc R . . C27 C 0.12965(8) 0.19018(8) 0.60832(16) 0.0275(3) Uani 1 1 d . . . C28 C 0.06017(9) 0.20250(10) 0.65776(18) 0.0371(4) Uani 1 1 d . . . H28 H 0.0233 0.2165 0.5963 0.044 Uiso 1 1 calc R . . C29 C 0.04253(9) 0.19526(10) 0.79170(17) 0.0388(4) Uani 1 1 d . . . H29 H -0.0055 0.2044 0.8201 0.047 Uiso 1 1 calc R . . C30 C 0.09451(9) 0.17482(9) 0.88432(17) 0.0337(4) Uani 1 1 d . . . H30 H 0.0827 0.1695 0.9765 0.040 Uiso 1 1 calc R . . C31 C 0.16337(9) 0.16232(9) 0.84067(16) 0.0307(4) Uani 1 1 d . . . H31 H 0.1997 0.1482 0.9031 0.037 Uiso 1 1 calc R . . C32 C 0.18057(8) 0.17010(8) 0.70532(15) 0.0270(3) Uani 1 1 d . . . H32 H 0.2288 0.1614 0.6781 0.032 Uiso 1 1 calc R . . C33 C 0.10785(8) 0.27849(9) 0.38902(16) 0.0303(3) Uani 1 1 d . . . C34 C 0.07474(9) 0.28234(10) 0.26307(17) 0.0355(4) Uani 1 1 d . . . H34 H 0.0764 0.2368 0.2067 0.043 Uiso 1 1 calc R . . C35 C 0.03945(10) 0.35058(11) 0.2174(2) 0.0456(5) Uani 1 1 d . . . H35 H 0.0174 0.3504 0.1316 0.055 Uiso 1 1 calc R . . C36 C 0.03642(10) 0.41783(11) 0.2953(2) 0.0497(5) Uani 1 1 d . . . H36 H 0.0129 0.4644 0.2639 0.060 Uiso 1 1 calc R . . C37 C 0.06812(10) 0.41638(11) 0.4199(2) 0.0491(5) Uani 1 1 d . . . H37 H 0.0664 0.4625 0.4750 0.059 Uiso 1 1 calc R . . C38 C 0.10239(9) 0.34848(10) 0.46564(19) 0.0403(4) Uani 1 1 d . . . H38 H 0.1231 0.3492 0.5526 0.048 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 C1 0.0326(9) 0.0279(8) 0.0297(9) 0.0058(6) -0.0072(7) 0.0034(7) N1 0.0354(8) 0.0318(7) 0.0348(8) -0.0042(6) -0.0034(7) 0.0028(6) C2 0.0521(11) 0.0394(10) 0.0556(12) -0.0158(9) -0.0076(10) 0.0020(9) C3 0.0566(12) 0.0312(8) 0.0381(10) 0.0001(8) -0.0139(9) -0.0023(8) C4 0.0542(11) 0.0374(10) 0.0554(12) -0.0057(8) -0.0055(10) -0.0132(9) N2 0.0367(8) 0.0310(7) 0.0410(8) -0.0014(6) -0.0036(7) -0.0031(6) C5 0.0347(9) 0.0461(10) 0.0417(10) -0.0031(8) -0.0026(8) 0.0036(8) C6 0.0288(8) 0.0401(10) 0.0588(12) 0.0005(8) -0.0030(9) 0.0013(8) C7 0.0462(11) 0.0467(11) 0.0709(14) -0.0057(10) 0.0143(11) -0.0062(9) C8 0.0846(16) 0.0525(11) 0.0535(13) 0.0046(10) 0.0165(13) 0.0045(12) C9 0.0265(8) 0.0290(8) 0.0323(9) 0.0013(7) -0.0013(7) 0.0015(6) C10 0.0319(9) 0.0379(9) 0.0329(9) 0.0035(7) -0.0056(8) 0.0018(7) C11 0.0353(9) 0.0477(10) 0.0356(9) -0.0088(8) -0.0027(8) 0.0012(8) C12 0.0368(9) 0.0339(9) 0.0531(12) -0.0107(8) 0.0034(9) -0.0031(7) C13 0.0482(10) 0.0295(8) 0.0482(11) 0.0049(8) 0.0064(9) -0.0011(8) C14 0.0425(10) 0.0333(9) 0.0317(9) 0.0039(7) 0.0015(8) 0.0001(7) B1 0.0284(9) 0.0305(9) 0.0235(8) 0.0049(7) -0.0016(7) -0.0041(7) C15 0.0326(8) 0.0333(8) 0.0214(7) 0.0068(6) 0.0007(7) -0.0054(7) C16 0.0330(9) 0.0367(9) 0.0288(8) 0.0056(7) -0.0001(7) -0.0054(7) C17 0.0330(9) 0.0498(10) 0.0318(9) 0.0013(8) -0.0010(8) 0.0005(8) C18 0.0284(8) 0.0600(11) 0.0297(9) 0.0020(8) 0.0004(7) -0.0088(8) C19 0.0404(10) 0.0475(10) 0.0360(10) 0.0016(8) 0.0019(8) -0.0188(8) C20 0.0373(9) 0.0359(9) 0.0316(9) 0.0016(7) 0.0040(8) -0.0071(7) C21 0.0292(8) 0.0315(8) 0.0308(9) 0.0077(7) -0.0068(7) -0.0018(7) C22 0.0328(9) 0.0370(9) 0.0342(9) 0.0040(7) -0.0047(8) -0.0026(7) C23 0.0462(10) 0.0401(10) 0.0380(10) -0.0018(8) -0.0079(9) 0.0067(8) C24 0.0506(11) 0.0298(8) 0.0510(11) -0.0010(8) -0.0220(10) -0.0012(8) C25 0.0473(10) 0.0364(9) 0.0486(11) 0.0104(8) -0.0139(9) -0.0120(8) C26 0.0378(9) 0.0379(9) 0.0344(9) 0.0082(8) -0.0067(8) -0.0080(7) C27 0.0260(8) 0.0254(7) 0.0312(8) 0.0029(6) -0.0005(7) -0.0060(6) C28 0.0272(8) 0.0479(10) 0.0362(9) 0.0121(8) -0.0041(8) -0.0021(7) C29 0.0273(9) 0.0487(10) 0.0404(11) 0.0088(8) 0.0078(8) -0.0002(7) C30 0.0380(9) 0.0348(8) 0.0284(8) 0.0024(7) 0.0048(7) -0.0049(7) C31 0.0339(9) 0.0305(8) 0.0278(9) -0.0007(7) -0.0056(7) -0.0011(7) C32 0.0268(8) 0.0261(7) 0.0281(8) -0.0001(6) -0.0002(7) -0.0016(6) C33 0.0267(8) 0.0324(8) 0.0317(9) 0.0085(7) 0.0020(7) -0.0051(6) C34 0.0323(9) 0.0415(9) 0.0326(9) 0.0085(7) 0.0011(8) -0.0017(7) C35 0.0377(10) 0.0567(11) 0.0424(10) 0.0184(9) -0.0018(9) 0.0034(9) C36 0.0422(11) 0.0410(10) 0.0659(14) 0.0211(10) 0.0072(10) 0.0048(8) C37 0.0517(11) 0.0323(9) 0.0632(13) 0.0067(9) 0.0070(11) -0.0003(8) C38 0.0421(10) 0.0359(9) 0.0429(11) 0.0036(8) -0.0031(8) -0.0030(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N2 1.322(2) . ? C1 N1 1.325(2) . ? C1 C9 1.489(2) . ? N1 C5 1.466(2) . ? N1 C2 1.471(2) . ? C2 C3 1.502(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.498(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 N2 1.477(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? N2 C6 1.477(2) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 C7 1.516(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.501(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C14 1.385(2) . ? C9 C10 1.389(2) . ? C10 C11 1.387(2) . ? C10 H10 0.9500 . ? C11 C12 1.377(3) . ? C11 H11 0.9500 . ? C12 C13 1.381(3) . ? C12 H12 0.9500 . ? C13 C14 1.383(2) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? B1 C21 1.647(2) . ? B1 C15 1.648(2) . ? B1 C27 1.653(2) . ? B1 C33 1.654(2) . ? C15 C20 1.396(2) . ? C15 C16 1.400(2) . ? C16 C17 1.391(2) . ? C16 H16 0.9500 . ? C17 C18 1.382(2) . ? C17 H17 0.9500 . ? C18 C19 1.372(3) . ? C18 H18 0.9500 . ? C19 C20 1.396(2) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C21 C26 1.400(2) . ? C21 C22 1.404(2) . ? C22 C23 1.390(2) . ? C22 H22 0.9500 . ? C23 C24 1.374(3) . ? C23 H23 0.9500 . ? C24 C25 1.381(3) . ? C24 H24 0.9500 . ? C25 C26 1.389(2) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 C32 1.397(2) . ? C27 C28 1.400(2) . ? C28 C29 1.383(2) . ? C28 H28 0.9500 . ? C29 C30 1.382(2) . ? C29 H29 0.9500 . ? C30 C31 1.370(2) . ? C30 H30 0.9500 . ? C31 C32 1.395(2) . ? C31 H31 0.9500 . ? C32 H32 0.9500 . ? C33 C34 1.402(2) . ? C33 C38 1.406(2) . ? C34 C35 1.398(2) . ? C34 H34 0.9500 . ? C35 C36 1.373(3) . ? C35 H35 0.9500 . ? C36 C37 1.377(3) . ? C36 H36 0.9500 . ? C37 C38 1.384(2) . ? C37 H37 0.9500 . ? C38 H38 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 N2 C1 N1 122.10(15) . . ? N2 C1 C9 119.78(14) . . ? N1 C1 C9 118.09(14) . . ? C1 N1 C5 122.92(14) . . ? C1 N1 C2 121.98(14) . . ? C5 N1 C2 115.09(14) . . ? N1 C2 C3 110.13(14) . . ? N1 C2 H2A 109.6 . . ? C3 C2 H2A 109.6 . . ? N1 C2 H2B 109.6 . . ? C3 C2 H2B 109.6 . . ? H2A C2 H2B 108.1 . . ? C2 C3 C4 109.46(16) . . ? C2 C3 H3A 109.8 . . ? C4 C3 H3A 109.8 . . ? C2 C3 H3B 109.8 . . ? C4 C3 H3B 109.8 . . ? H3A C3 H3B 108.2 . . ? N2 C4 C3 110.44(14) . . ? N2 C4 H4A 109.6 . . ? C3 C4 H4A 109.6 . . ? N2 C4 H4B 109.6 . . ? C3 C4 H4B 109.6 . . ? H4A C4 H4B 108.1 . . ? C1 N2 C4 120.90(15) . . ? C1 N2 C6 122.74(14) . . ? C4 N2 C6 115.96(14) . . ? N1 C5 H5A 109.5 . . ? N1 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N1 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N2 C6 C7 112.60(15) . . ? N2 C6 H6A 109.1 . . ? C7 C6 H6A 109.1 . . ? N2 C6 H6B 109.1 . . ? C7 C6 H6B 109.1 . . ? H6A C6 H6B 107.8 . . ? C8 C7 C6 113.42(17) . . ? C8 C7 H7A 108.9 . . ? C6 C7 H7A 108.9 . . ? C8 C7 H7B 108.9 . . ? C6 C7 H7B 108.9 . . ? H7A C7 H7B 107.7 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C14 C9 C10 120.25(15) . . ? C14 C9 C1 117.98(14) . . ? C10 C9 C1 121.77(14) . . ? C9 C10 C11 119.68(15) . . ? C9 C10 H10 120.2 . . ? C11 C10 H10 120.2 . . ? C12 C11 C10 119.90(17) . . ? C12 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? C11 C12 C13 120.36(16) . . ? C11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? C12 C13 C14 120.25(16) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C13 C14 C9 119.56(16) . . ? C13 C14 H14 120.2 . . ? C9 C14 H14 120.2 . . ? C21 B1 C15 109.84(13) . . ? C21 B1 C27 110.16(13) . . ? C15 B1 C27 107.19(13) . . ? C21 B1 C33 110.23(13) . . ? C15 B1 C33 111.32(12) . . ? C27 B1 C33 108.03(13) . . ? C20 C15 C16 114.63(14) . . ? C20 C15 B1 122.56(14) . . ? C16 C15 B1 122.44(13) . . ? C17 C16 C15 123.32(15) . . ? C17 C16 H16 118.3 . . ? C15 C16 H16 118.3 . . ? C18 C17 C16 120.06(17) . . ? C18 C17 H17 120.0 . . ? C16 C17 H17 120.0 . . ? C19 C18 C17 118.51(16) . . ? C19 C18 H18 120.7 . . ? C17 C18 H18 120.7 . . ? C18 C19 C20 120.88(16) . . ? C18 C19 H19 119.6 . . ? C20 C19 H19 119.6 . . ? C19 C20 C15 122.60(16) . . ? C19 C20 H20 118.7 . . ? C15 C20 H20 118.7 . . ? C26 C21 C22 114.48(15) . . ? C26 C21 B1 124.08(15) . . ? C22 C21 B1 121.44(14) . . ? C23 C22 C21 123.03(16) . . ? C23 C22 H22 118.5 . . ? C21 C22 H22 118.5 . . ? C24 C23 C22 120.37(17) . . ? C24 C23 H23 119.8 . . ? C22 C23 H23 119.8 . . ? C23 C24 C25 118.72(16) . . ? C23 C24 H24 120.6 . . ? C25 C24 H24 120.6 . . ? C24 C25 C26 120.41(17) . . ? C24 C25 H25 119.8 . . ? C26 C25 H25 119.8 . . ? C25 C26 C21 122.99(17) . . ? C25 C26 H26 118.5 . . ? C21 C26 H26 118.5 . . ? C32 C27 C28 114.73(15) . . ? C32 C27 B1 123.24(14) . . ? C28 C27 B1 122.03(14) . . ? C29 C28 C27 123.21(16) . . ? C29 C28 H28 118.4 . . ? C27 C28 H28 118.4 . . ? C30 C29 C28 120.19(16) . . ? C30 C29 H29 119.9 . . ? C28 C29 H29 119.9 . . ? C31 C30 C29 118.72(15) . . ? C31 C30 H30 120.6 . . ? C29 C30 H30 120.6 . . ? C30 C31 C32 120.56(15) . . ? C30 C31 H31 119.7 . . ? C32 C31 H31 119.7 . . ? C31 C32 C27 122.59(15) . . ? C31 C32 H32 118.7 . . ? C27 C32 H32 118.7 . . ? C34 C33 C38 114.70(14) . . ? C34 C33 B1 123.76(14) . . ? C38 C33 B1 121.53(14) . . ? C35 C34 C33 122.51(17) . . ? C35 C34 H34 118.7 . . ? C33 C34 H34 118.7 . . ? C36 C35 C34 120.58(18) . . ? C36 C35 H35 119.7 . . ? C34 C35 H35 119.7 . . ? C35 C36 C37 118.69(17) . . ? C35 C36 H36 120.7 . . ? C37 C36 H36 120.7 . . ? C36 C37 C38 120.68(19) . . ? C36 C37 H37 119.7 . . ? C38 C37 H37 119.7 . . ? C37 C38 C33 122.84(17) . . ? C37 C38 H38 118.6 . . ? C33 C38 H38 118.6 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.143 _refine_diff_density_min -0.145 _refine_diff_density_rms 0.029 # Attachment '- 48.cif' data_e510a _database_code_depnum_ccdc_archive 'CCDC 753168' #TrackingRef '- 48.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H36 I2 N4' _chemical_formula_sum 'C22 H36 I2 N4' _chemical_formula_weight 610.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.6986(4) _cell_length_b 13.1654(8) _cell_length_c 12.2445(8) _cell_angle_alpha 90.00 _cell_angle_beta 98.824(2) _cell_angle_gamma 90.00 _cell_volume 1226.35(13) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6473 _cell_measurement_theta_min 2.93 _cell_measurement_theta_max 29.37 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.653 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 604 _exptl_absorpt_coefficient_mu 2.579 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7825 _exptl_absorpt_correction_T_max 0.8819 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19439 _diffrn_reflns_av_R_equivalents 0.0368 _diffrn_reflns_av_sigmaI/netI 0.0294 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.94 _diffrn_reflns_theta_max 30.06 _reflns_number_total 3545 _reflns_number_gt 2903 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0556P)^2^+0.1966P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3545 _refine_ls_number_parameters 126 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0406 _refine_ls_R_factor_gt 0.0313 _refine_ls_wR_factor_ref 0.0928 _refine_ls_wR_factor_gt 0.0889 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_restrained_S_all 1.090 _refine_ls_shift/su_max 0.004 _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 I1 I 0.05866(2) 0.336449(13) 0.258395(15) 0.03304(8) Uani 1 1 d . . . C1 C 0.7906(3) 0.06660(17) 0.2980(2) 0.0228(5) Uani 1 1 d . . . N1 N 0.6331(3) 0.10663(17) 0.29937(17) 0.0279(5) Uani 1 1 d . . . C2 C 0.5242(5) 0.1400(3) 0.1971(3) 0.0481(7) Uani 1 1 d . . . C3 C 0.5753(9) 0.0971(7) 0.0988(5) 0.0481(7) Uani 0.50 1 d P . . C3A C 0.6298(10) 0.1659(6) 0.1117(6) 0.0481(7) Uani 0.50 1 d P . . C4 C 0.7663(4) 0.0887(3) 0.0977(2) 0.0424(7) Uani 1 1 d . . . N2 N 0.8579(3) 0.05494(17) 0.20595(18) 0.0284(5) Uani 1 1 d . . . C5 C 0.5466(4) 0.1105(2) 0.3990(2) 0.0307(6) Uani 1 1 d . . . H5A H 0.6230 0.0768 0.4608 0.037 Uiso 1 1 calc R . . H5B H 0.4347 0.0722 0.3846 0.037 Uiso 1 1 calc R . . C6 C 0.5087(4) 0.2187(2) 0.4329(2) 0.0361(6) Uani 1 1 d . . . H6A H 0.4354 0.2532 0.3702 0.043 Uiso 1 1 calc R . . H6B H 0.4408 0.2164 0.4953 0.043 Uiso 1 1 calc R . . C7 C 0.6751(4) 0.2799(3) 0.4671(3) 0.0480(8) Uani 1 1 d . . . H7A H 0.7515 0.2441 0.5261 0.072 Uiso 1 1 calc R . . H7B H 0.6445 0.3468 0.4938 0.072 Uiso 1 1 calc R . . H7C H 0.7368 0.2885 0.4034 0.072 Uiso 1 1 calc R . . C8 C 1.0363(4) 0.0157(3) 0.2049(3) 0.0456(8) Uani 1 1 d . . . H8A H 1.1164 0.0724 0.1984 0.068 Uiso 1 1 calc R . . H8B H 1.0358 -0.0303 0.1420 0.068 Uiso 1 1 calc R . . H8C H 1.0756 -0.0213 0.2738 0.068 Uiso 1 1 calc R . . C9 C 0.8979(3) 0.03318(17) 0.4043(2) 0.0235(5) Uani 1 1 d . . . C10 C 1.0299(3) 0.09536(18) 0.4574(2) 0.0285(5) Uani 1 1 d . . . H10 H 1.0495 0.1604 0.4279 0.034 Uiso 1 1 calc R . . C11 C 1.1322(3) 0.06253(18) 0.5528(2) 0.0273(5) Uani 1 1 d . . . H11 H 1.2231 0.1047 0.5894 0.033 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 I1 0.03048(13) 0.03333(12) 0.03248(12) 0.00731(6) -0.00420(8) -0.00114(6) C1 0.0208(11) 0.0223(10) 0.0227(11) 0.0034(9) -0.0045(9) -0.0016(8) N1 0.0215(11) 0.0397(12) 0.0202(10) 0.0059(9) -0.0040(9) 0.0062(9) C2 0.0356(15) 0.082(2) 0.0239(12) 0.0137(13) -0.0033(11) 0.0187(14) C3 0.0356(15) 0.082(2) 0.0239(12) 0.0137(13) -0.0033(11) 0.0187(14) C3A 0.0356(15) 0.082(2) 0.0239(12) 0.0137(13) -0.0033(11) 0.0187(14) C4 0.0359(16) 0.068(2) 0.0222(13) 0.0071(13) 0.0000(12) 0.0114(14) N2 0.0241(11) 0.0356(11) 0.0241(11) 0.0030(9) -0.0003(9) 0.0054(9) C5 0.0267(14) 0.0393(14) 0.0256(13) 0.0041(10) 0.0021(11) 0.0020(10) C6 0.0319(15) 0.0443(15) 0.0319(14) -0.0007(12) 0.0045(12) 0.0048(12) C7 0.0402(18) 0.0568(19) 0.0483(19) -0.0126(15) 0.0108(15) -0.0054(14) C8 0.0318(15) 0.068(2) 0.0365(17) -0.0001(15) 0.0034(13) 0.0187(15) C9 0.0206(11) 0.0247(11) 0.0229(11) 0.0043(9) -0.0044(9) -0.0008(8) C10 0.0261(13) 0.0250(11) 0.0317(13) 0.0095(10) -0.0045(11) -0.0045(9) C11 0.0226(12) 0.0249(11) 0.0307(13) 0.0046(10) -0.0083(10) -0.0062(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N2 1.320(3) . ? C1 N1 1.324(3) . ? C1 C9 1.496(3) . ? N1 C2 1.464(4) . ? N1 C5 1.477(3) . ? C2 C3 1.437(7) . ? C2 C3A 1.459(8) . ? C3 C4 1.477(7) . ? C3A C4 1.491(7) . ? C4 N2 1.471(4) . ? N2 C8 1.469(4) . ? C5 C6 1.524(4) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.517(4) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.387(3) . ? C9 C11 1.398(3) 3_756 ? C10 C11 1.375(4) . ? C10 H10 0.9500 . ? C11 C9 1.398(3) 3_756 ? C11 H11 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 N2 C1 N1 122.5(2) . . ? N2 C1 C9 118.1(2) . . ? N1 C1 C9 119.4(2) . . ? C1 N1 C2 120.9(2) . . ? C1 N1 C5 123.6(2) . . ? C2 N1 C5 115.1(2) . . ? C3 C2 N1 113.8(4) . . ? C3A C2 N1 112.0(4) . . ? C2 C3 C4 115.9(5) . . ? C2 C3A C4 113.8(5) . . ? N2 C4 C3 110.8(3) . . ? N2 C4 C3A 110.6(3) . . ? C1 N2 C8 122.6(2) . . ? C1 N2 C4 122.5(2) . . ? C8 N2 C4 114.7(2) . . ? N1 C5 C6 112.7(2) . . ? N1 C5 H5A 109.0 . . ? C6 C5 H5A 109.0 . . ? N1 C5 H5B 109.0 . . ? C6 C5 H5B 109.0 . . ? H5A C5 H5B 107.8 . . ? C7 C6 C5 112.5(2) . . ? C7 C6 H6A 109.1 . . ? C5 C6 H6A 109.1 . . ? C7 C6 H6B 109.1 . . ? C5 C6 H6B 109.1 . . ? H6A C6 H6B 107.8 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N2 C8 H8A 109.5 . . ? N2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 C11 120.5(2) . 3_756 ? C10 C9 C1 120.1(2) . . ? C11 C9 C1 119.4(2) 3_756 . ? C11 C10 C9 119.7(2) . . ? C11 C10 H10 120.1 . . ? C9 C10 H10 120.1 . . ? C10 C11 C9 119.8(2) . 3_756 ? C10 C11 H11 120.1 . . ? C9 C11 H11 120.1 3_756 . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 30.06 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 1.474 _refine_diff_density_min -0.928 _refine_diff_density_rms 0.110 # Attachment '- 59.cif' data_e683a _database_code_depnum_ccdc_archive 'CCDC 753169' #TrackingRef '- 59.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C40 H72 N4, 2Br, 3( H2 O)' _chemical_formula_sum 'C40 H78 Br2 N4 O3' _chemical_formula_weight 822.88 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' Br Br -0.2901 2.4595 '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' H H 0.0000 0.0000 '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 7.4346(2) _cell_length_b 12.6309(3) _cell_length_c 24.8045(7) _cell_angle_alpha 81.5990(10) _cell_angle_beta 88.3960(10) _cell_angle_gamma 73.3400(10) _cell_volume 2207.33(10) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 8783 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.238 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 1.874 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8347 _exptl_absorpt_correction_T_max 0.8645 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 49155 _diffrn_reflns_av_R_equivalents 0.0244 _diffrn_reflns_av_sigmaI/netI 0.0263 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 30.38 _reflns_number_total 13224 _reflns_number_gt 10187 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.1006P)^2^+5.2794P] 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 13224 _refine_ls_number_parameters 408 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0778 _refine_ls_R_factor_gt 0.0600 _refine_ls_wR_factor_ref 0.2039 _refine_ls_wR_factor_gt 0.1898 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _refine_ls_shift/su_max 0.002 _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 Br1 Br 0.17924(5) 0.87073(3) 0.806868(16) 0.03717(11) Uani 1 1 d . . . Br2 Br 0.45755(5) 0.28041(3) 0.889135(15) 0.03331(11) Uani 1 1 d . . . C1 C 1.0540(4) 0.6642(2) 0.11774(12) 0.0224(5) Uani 1 1 d . . . N1 N 1.0266(5) 0.7343(2) 0.15372(12) 0.0322(6) Uani 1 1 d . . . C2 C 0.9509(9) 0.8553(3) 0.13627(19) 0.0571(13) Uani 1 1 d . . . H2A H 0.8122 0.8767 0.1382 0.069 Uiso 1 1 calc R . . H2B H 0.9975 0.8960 0.1614 0.069 Uiso 1 1 calc R . . C3 C 1.0061(8) 0.8880(3) 0.0805(2) 0.0505(11) Uani 1 1 d . . . H3A H 1.1427 0.8792 0.0798 0.061 Uiso 1 1 calc R . . H3B H 0.9397 0.9675 0.0683 0.061 Uiso 1 1 calc R . . C4 C 0.9595(5) 0.8178(3) 0.04267(14) 0.0315(7) Uani 1 1 d . . . H4A H 0.8217 0.8388 0.0371 0.038 Uiso 1 1 calc R . . H4B H 1.0174 0.8314 0.0069 0.038 Uiso 1 1 calc R . . N2 N 1.0288(4) 0.6984(2) 0.06513(11) 0.0242(5) Uani 1 1 d . . . C5 C 1.0478(6) 0.6979(3) 0.21272(14) 0.0342(7) Uani 1 1 d . . . H5A H 1.1385 0.7306 0.2277 0.041 Uiso 1 1 calc R . . H5B H 1.0985 0.6156 0.2199 0.041 Uiso 1 1 calc R . . C6 C 0.8619(6) 0.7336(4) 0.24089(15) 0.0410(9) Uani 1 1 d . . . H6A H 0.7730 0.6991 0.2264 0.049 Uiso 1 1 calc R . . H6B H 0.8097 0.8156 0.2323 0.049 Uiso 1 1 calc R . . C7 C 0.8775(6) 0.7009(3) 0.30268(14) 0.0346(7) Uani 1 1 d . . . H7A H 0.8978 0.6194 0.3120 0.042 Uiso 1 1 calc R . . H7B H 0.9868 0.7193 0.3166 0.042 Uiso 1 1 calc R . . C8 C 0.6995(6) 0.7626(3) 0.32971(14) 0.0367(8) Uani 1 1 d . . . H8A H 0.5937 0.7383 0.3177 0.044 Uiso 1 1 calc R . . H8B H 0.6729 0.8435 0.3164 0.044 Uiso 1 1 calc R . . C9 C 0.7048(5) 0.7462(3) 0.39185(14) 0.0326(7) Uani 1 1 d . . . H9A H 0.8163 0.7641 0.4045 0.039 Uiso 1 1 calc R . . H9B H 0.7167 0.6669 0.4059 0.039 Uiso 1 1 calc R . . C10 C 0.5281(5) 0.8201(3) 0.41474(14) 0.0345(7) Uani 1 1 d . . . H10A H 0.5121 0.8985 0.3981 0.041 Uiso 1 1 calc R . . H10B H 0.4183 0.7984 0.4036 0.041 Uiso 1 1 calc R . . C11 C 0.5282(5) 0.8144(3) 0.47638(14) 0.0334(7) Uani 1 1 d . . . H11A H 0.5406 0.7366 0.4933 0.040 Uiso 1 1 calc R . . H11B H 0.6385 0.8351 0.4879 0.040 Uiso 1 1 calc R . . C12 C 0.3511(5) 0.8911(3) 0.49687(15) 0.0346(7) Uani 1 1 d . . . H12A H 0.2415 0.8695 0.4856 0.041 Uiso 1 1 calc R . . H12B H 0.3380 0.9685 0.4791 0.041 Uiso 1 1 calc R . . C13 C 0.3471(5) 0.8892(3) 0.55836(15) 0.0353(7) Uani 1 1 d . . . H13A H 0.3602 0.8119 0.5762 0.042 Uiso 1 1 calc R . . H13B H 0.4563 0.9112 0.5698 0.042 Uiso 1 1 calc R . . C14 C 0.1688(5) 0.9663(3) 0.57795(15) 0.0336(7) Uani 1 1 d . . . H14A H 0.0600 0.9437 0.5668 0.040 Uiso 1 1 calc R . . H14B H 0.1552 1.0433 0.5597 0.040 Uiso 1 1 calc R . . C15 C 0.1637(6) 0.9662(4) 0.63931(15) 0.0389(8) Uani 1 1 d . . . H15A H 0.1760 0.8894 0.6577 0.047 Uiso 1 1 calc R . . H15B H 0.2726 0.9885 0.6506 0.047 Uiso 1 1 calc R . . C16 C -0.0153(6) 1.0444(4) 0.65799(18) 0.0457(9) Uani 1 1 d . . . H16A H -0.0266 1.1210 0.6408 0.069 Uiso 1 1 calc R . . H16B H -0.0110 1.0405 0.6977 0.069 Uiso 1 1 calc R . . H16C H -0.1237 1.0220 0.6475 0.069 Uiso 1 1 calc R . . C17 C 1.0410(5) 0.6222(3) 0.02534(14) 0.0327(7) Uani 1 1 d . . . H17A H 1.1196 0.5477 0.0403 0.049 Uiso 1 1 calc R . . H17B H 1.0968 0.6494 -0.0082 0.049 Uiso 1 1 calc R . . H17C H 0.9149 0.6185 0.0172 0.049 Uiso 1 1 calc R . . C18 C 1.1162(4) 0.5415(2) 0.13685(12) 0.0218(5) Uani 1 1 d . . . C19 C 0.9837(4) 0.4843(3) 0.14900(14) 0.0268(6) Uani 1 1 d . . . H19 H 0.8537 0.5233 0.1467 0.032 Uiso 1 1 calc R . . C20 C 1.0421(4) 0.3687(2) 0.16473(14) 0.0257(6) Uani 1 1 d . . . H20 H 0.9525 0.3284 0.1732 0.031 Uiso 1 1 calc R . . C21 C 1.2338(4) 0.3134(2) 0.16785(12) 0.0213(5) Uani 1 1 d . . . C22 C 1.3666(4) 0.3713(2) 0.15591(14) 0.0253(6) Uani 1 1 d . . . H22 H 1.4967 0.3326 0.1585 0.030 Uiso 1 1 calc R . . C23 C 1.3080(4) 0.4859(3) 0.14028(14) 0.0259(6) Uani 1 1 d . . . H23 H 1.3975 0.5263 0.1320 0.031 Uiso 1 1 calc R . . C24 C 1.2984(4) 0.1897(2) 0.18135(12) 0.0220(5) Uani 1 1 d . . . N3 N 1.3483(4) 0.1436(2) 0.23202(11) 0.0292(6) Uani 1 1 d . B . C25 C 1.4236(6) 0.0224(3) 0.24657(16) 0.0410(9) Uani 1 1 d . . . H25A H 1.3908 0.0000 0.2847 0.049 Uiso 1 1 calc R . . H25B H 1.5622 0.0008 0.2441 0.049 Uiso 1 1 calc R . . C26 C 1.3453(6) -0.0368(3) 0.20925(19) 0.0437(9) Uani 1 1 d . . . H26A H 1.2096 -0.0253 0.2160 0.052 Uiso 1 1 calc R . . H26B H 1.4091 -0.1180 0.2164 0.052 Uiso 1 1 calc R . . C27 C 1.3736(7) 0.0073(3) 0.15109(18) 0.0435(9) Uani 1 1 d . . . H27A H 1.5085 -0.0180 0.1424 0.052 Uiso 1 1 calc R . . H27B H 1.3037 -0.0229 0.1267 0.052 Uiso 1 1 calc R . . N4 N 1.3082(4) 0.1296(2) 0.14162(11) 0.0259(5) Uani 1 1 d . . . C28 C 1.3463(5) 0.2099(3) 0.27600(14) 0.0345(7) Uani 1 1 d . . . H28A H 1.4684 0.1797 0.2957 0.041 Uiso 1 1 calc R A 1 H28B H 1.3380 0.2872 0.2591 0.041 Uiso 1 1 calc R A 1 C29 C 1.1451(14) 0.2377(13) 0.3031(4) 0.0696(8) Uani 0.532(7) 1 d P B 2 H29A H 1.0541 0.2983 0.2795 0.084 Uiso 0.532(7) 1 calc PR B 2 H29B H 1.0987 0.1709 0.3086 0.084 Uiso 0.532(7) 1 calc PR B 2 C29A C 1.2008(16) 0.2151(15) 0.3153(5) 0.0696(8) Uani 0.468(7) 1 d P B 1 H29C H 1.0818 0.2403 0.2940 0.084 Uiso 0.468(7) 1 calc PR B 1 H29D H 1.2144 0.1367 0.3315 0.084 Uiso 0.468(7) 1 calc PR B 1 C30 C 1.1690(7) 0.2751(6) 0.35878(19) 0.0696(8) Uani 1 1 d . . . C31 C 0.9757(14) 0.3117(13) 0.3865(4) 0.0696(8) Uani 0.532(7) 1 d P B 2 H31A H 0.8929 0.3773 0.3635 0.084 Uiso 0.532(7) 1 calc PR B 2 H31B H 0.9160 0.2504 0.3897 0.084 Uiso 0.532(7) 1 calc PR B 2 C31A C 1.0446(16) 0.2843(14) 0.4001(5) 0.0696(8) Uani 0.468(7) 1 d P B 1 H31C H 1.0687 0.2058 0.4176 0.084 Uiso 0.468(7) 1 calc PR B 1 H31D H 0.9231 0.3016 0.3805 0.084 Uiso 0.468(7) 1 calc PR B 1 C32 C 0.9964(7) 0.3415(6) 0.44308(19) 0.0696(8) Uani 1 1 d . . . C33 C 0.8070(14) 0.3801(13) 0.4716(4) 0.0696(8) Uani 0.532(7) 1 d P B 2 H33A H 0.7269 0.4481 0.4495 0.084 Uiso 0.532(7) 1 calc PR B 2 H33B H 0.7424 0.3212 0.4737 0.084 Uiso 0.532(7) 1 calc PR B 2 C33A C 0.8809(16) 0.3494(14) 0.4853(4) 0.0696(8) Uani 0.468(7) 1 d P B 1 H33C H 0.9126 0.2708 0.5031 0.084 Uiso 0.468(7) 1 calc PR B 1 H33D H 0.7581 0.3626 0.4670 0.084 Uiso 0.468(7) 1 calc PR B 1 C34 C 0.8292(7) 0.4052(6) 0.52883(19) 0.0696(8) Uani 1 1 d . . . C35A C 0.7173(16) 0.4098(14) 0.5716(4) 0.0696(8) Uani 0.468(7) 1 d P B 1 H35A H 0.7543 0.3311 0.5893 0.084 Uiso 0.468(7) 1 calc PR B 1 H35B H 0.5937 0.4207 0.5543 0.084 Uiso 0.468(7) 1 calc PR B 1 C35 C 0.6450(14) 0.4450(13) 0.5584(4) 0.0696(8) Uani 0.532(7) 1 d P B 2 H35C H 0.5668 0.5147 0.5371 0.084 Uiso 0.532(7) 1 calc PR B 2 H35D H 0.5765 0.3880 0.5598 0.084 Uiso 0.532(7) 1 calc PR B 2 C36 C 0.6678(7) 0.4664(6) 0.61549(19) 0.0696(8) Uani 1 1 d . . . C37 C 0.4919(17) 0.5009(16) 0.6473(5) 0.0755(13) Uani 0.532(7) 1 d P B 2 H37A H 0.4069 0.5681 0.6259 0.091 Uiso 0.532(7) 1 calc PR B 2 H37B H 0.4299 0.4407 0.6497 0.091 Uiso 0.532(7) 1 calc PR B 2 C37A C 0.5500(19) 0.4698(18) 0.6579(6) 0.0755(13) Uani 0.468(7) 1 d P B 1 H37C H 0.5803 0.3905 0.6745 0.091 Uiso 0.468(7) 1 calc PR B 1 H37D H 0.4261 0.4858 0.6398 0.091 Uiso 0.468(7) 1 calc PR B 1 C38 C 0.5067(8) 0.5259(7) 0.7026(2) 0.0755(13) Uani 1 1 d . . . C39 C 0.3550(8) 0.5434(7) 0.7393(2) 0.0755(13) Uani 1 1 d . B . H39A H 0.2426 0.5383 0.7214 0.113 Uiso 1 1 calc R . . H39B H 0.3309 0.6176 0.7503 0.113 Uiso 1 1 calc R . . H39C H 0.3866 0.4864 0.7715 0.113 Uiso 1 1 calc R . . C40 C 1.2408(5) 0.1798(3) 0.08650(14) 0.0341(7) Uani 1 1 d . . . H40A H 1.1053 0.1904 0.0841 0.051 Uiso 1 1 calc R . . H40B H 1.3054 0.1305 0.0606 0.051 Uiso 1 1 calc R . . H40C H 1.2664 0.2523 0.0778 0.051 Uiso 1 1 calc R . . O1 O 0.4619(6) 0.3949(3) 0.00540(16) 0.0650(10) Uani 1 1 d . . . O2 O 0.2916(6) 0.7991(4) 0.93820(15) 0.0707(11) Uani 1 1 d . . . O3 O 0.6077(5) 0.0726(3) 0.99145(14) 0.0590(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.03485(19) 0.02874(18) 0.0457(2) -0.00311(14) -0.00071(15) -0.00647(14) Br2 0.02768(17) 0.02413(16) 0.0468(2) -0.00195(13) -0.00467(13) -0.00640(12) C1 0.0219(13) 0.0167(12) 0.0284(14) -0.0036(10) 0.0025(10) -0.0053(10) N1 0.0499(17) 0.0171(12) 0.0282(13) -0.0047(10) 0.0034(12) -0.0070(11) C2 0.102(4) 0.0191(16) 0.045(2) -0.0050(15) 0.007(2) -0.009(2) C3 0.069(3) 0.0271(18) 0.054(3) -0.0014(17) -0.006(2) -0.0132(19) C4 0.0386(17) 0.0184(13) 0.0329(16) 0.0038(11) -0.0007(13) -0.0042(12) N2 0.0264(12) 0.0168(11) 0.0273(12) -0.0019(9) 0.0009(10) -0.0037(9) C5 0.047(2) 0.0264(15) 0.0269(15) -0.0063(12) -0.0002(14) -0.0052(14) C6 0.047(2) 0.042(2) 0.0253(16) -0.0038(14) -0.0009(14) -0.0004(17) C7 0.0443(19) 0.0288(16) 0.0270(15) -0.0051(12) -0.0014(14) -0.0037(14) C8 0.044(2) 0.0322(17) 0.0271(16) -0.0028(13) -0.0003(14) -0.0009(15) C9 0.0382(17) 0.0315(16) 0.0260(15) -0.0016(12) -0.0015(13) -0.0079(14) C10 0.0397(18) 0.0325(17) 0.0287(16) -0.0018(13) 0.0015(13) -0.0077(14) C11 0.0340(17) 0.0380(18) 0.0281(15) -0.0027(13) 0.0016(13) -0.0114(14) C12 0.0372(18) 0.0351(17) 0.0304(16) -0.0026(13) 0.0011(13) -0.0099(14) C13 0.0327(17) 0.0419(19) 0.0308(16) -0.0043(14) 0.0012(13) -0.0104(15) C14 0.0344(17) 0.0348(17) 0.0318(16) -0.0038(13) 0.0011(13) -0.0107(14) C15 0.0382(19) 0.044(2) 0.0325(17) -0.0033(15) 0.0038(14) -0.0092(16) C16 0.047(2) 0.045(2) 0.044(2) -0.0087(17) 0.0124(18) -0.0116(18) C17 0.0414(18) 0.0268(15) 0.0296(16) -0.0069(12) -0.0009(13) -0.0078(14) C18 0.0219(13) 0.0160(12) 0.0262(13) -0.0030(10) 0.0019(10) -0.0036(10) C19 0.0190(12) 0.0203(13) 0.0373(16) 0.0003(11) 0.0016(11) -0.0017(10) C20 0.0207(13) 0.0192(13) 0.0360(16) -0.0005(11) 0.0023(11) -0.0056(10) C21 0.0232(13) 0.0155(11) 0.0237(13) -0.0022(9) -0.0003(10) -0.0033(10) C22 0.0186(12) 0.0189(13) 0.0366(16) -0.0045(11) 0.0001(11) -0.0023(10) C23 0.0203(13) 0.0209(13) 0.0369(16) -0.0057(11) 0.0025(11) -0.0062(11) C24 0.0220(12) 0.0167(12) 0.0244(13) -0.0022(10) 0.0030(10) -0.0014(10) N3 0.0330(14) 0.0225(12) 0.0242(12) -0.0009(10) 0.0010(10) 0.0034(10) C25 0.048(2) 0.0231(15) 0.0367(18) 0.0068(13) 0.0032(16) 0.0080(15) C26 0.044(2) 0.0172(14) 0.064(3) -0.0007(15) 0.0105(19) -0.0033(14) C27 0.057(2) 0.0193(15) 0.051(2) -0.0139(15) 0.0067(18) -0.0020(15) N4 0.0301(13) 0.0189(11) 0.0272(13) -0.0066(9) 0.0024(10) -0.0033(10) C28 0.0368(17) 0.0353(17) 0.0245(15) -0.0073(13) -0.0042(13) 0.0023(14) C29 0.0382(10) 0.126(2) 0.0361(10) -0.0390(12) 0.0003(8) 0.0031(12) C29A 0.0382(10) 0.126(2) 0.0361(10) -0.0390(12) 0.0003(8) 0.0031(12) C30 0.0382(10) 0.126(2) 0.0361(10) -0.0390(12) 0.0003(8) 0.0031(12) C31 0.0382(10) 0.126(2) 0.0361(10) -0.0390(12) 0.0003(8) 0.0031(12) C31A 0.0382(10) 0.126(2) 0.0361(10) -0.0390(12) 0.0003(8) 0.0031(12) C32 0.0382(10) 0.126(2) 0.0361(10) -0.0390(12) 0.0003(8) 0.0031(12) C33 0.0382(10) 0.126(2) 0.0361(10) -0.0390(12) 0.0003(8) 0.0031(12) C33A 0.0382(10) 0.126(2) 0.0361(10) -0.0390(12) 0.0003(8) 0.0031(12) C34 0.0382(10) 0.126(2) 0.0361(10) -0.0390(12) 0.0003(8) 0.0031(12) C35A 0.0382(10) 0.126(2) 0.0361(10) -0.0390(12) 0.0003(8) 0.0031(12) C35 0.0382(10) 0.126(2) 0.0361(10) -0.0390(12) 0.0003(8) 0.0031(12) C36 0.0382(10) 0.126(2) 0.0361(10) -0.0390(12) 0.0003(8) 0.0031(12) C37 0.056(2) 0.143(4) 0.0492(18) -0.054(2) 0.0202(15) -0.046(2) C37A 0.056(2) 0.143(4) 0.0492(18) -0.054(2) 0.0202(15) -0.046(2) C38 0.056(2) 0.143(4) 0.0492(18) -0.054(2) 0.0202(15) -0.046(2) C39 0.056(2) 0.143(4) 0.0492(18) -0.054(2) 0.0202(15) -0.046(2) C40 0.0404(18) 0.0377(18) 0.0243(15) -0.0091(13) 0.0005(13) -0.0090(15) O1 0.066(2) 0.070(2) 0.064(2) -0.0297(19) 0.0053(18) -0.0180(19) O2 0.057(2) 0.105(3) 0.0451(19) -0.003(2) 0.0008(16) -0.019(2) O3 0.067(2) 0.0455(18) 0.0507(19) 0.0064(14) 0.0080(16) -0.0018(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N2 1.314(4) . ? C1 N1 1.319(4) . ? C1 C18 1.492(4) . ? N1 C5 1.467(4) . ? N1 C2 1.472(5) . ? C2 C3 1.466(7) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.491(6) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 N2 1.475(4) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? N2 C17 1.459(4) . ? C5 C6 1.511(6) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.527(5) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.523(5) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.525(5) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.526(5) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.520(5) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.518(5) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.522(5) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.518(5) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.521(5) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.519(6) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 C19 1.382(4) . ? C18 C23 1.396(4) . ? C19 C20 1.397(4) . ? C19 H19 0.9500 . ? C20 C21 1.395(4) . ? C20 H20 0.9500 . ? C21 C22 1.390(4) . ? C21 C24 1.487(4) . ? C22 C23 1.385(4) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? C24 N4 1.317(4) . ? C24 N3 1.321(4) . ? N3 C25 1.465(4) . ? N3 C28 1.466(4) . ? C25 C26 1.496(6) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 C27 1.500(6) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 N4 1.465(4) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? N4 C40 1.458(4) . ? C28 C29A 1.430(12) . ? C28 C29 1.589(11) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 C30 1.553(10) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C29A C30 1.383(12) . ? C29A H29C 0.9900 . ? C29A H29D 0.9900 . ? C30 C31A 1.357(11) . ? C30 C31 1.552(10) . ? C31 C32 1.528(10) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C31A C32 1.357(11) . ? C31A H31C 0.9900 . ? C31A H31D 0.9900 . ? C32 C33A 1.333(11) . ? C32 C33 1.541(10) . ? C33 C34 1.522(10) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C33A C34 1.362(11) . ? C33A H33C 0.9900 . ? C33A H33D 0.9900 . ? C34 C35A 1.326(11) . ? C34 C35 1.524(10) . ? C35A C36 1.375(11) . ? C35A H35A 0.9900 . ? C35A H35B 0.9900 . ? C35 C36 1.502(10) . ? C35 H35C 0.9900 . ? C35 H35D 0.9900 . ? C36 C37A 1.347(14) . ? C36 C37 1.496(12) . ? C37 C38 1.467(12) . ? C37 H37A 0.9900 . ? C37 H37B 0.9900 . ? C37A C38 1.385(14) . ? C37A H37C 0.9900 . ? C37A H37D 0.9900 . ? C38 C39 1.416(7) . ? C39 H39A 0.9800 . ? C39 H39B 0.9800 . ? C39 H39C 0.9800 . ? C40 H40A 0.9800 . ? C40 H40B 0.9800 . ? C40 H40C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 C1 N1 122.3(3) . . ? N2 C1 C18 118.2(3) . . ? N1 C1 C18 119.4(3) . . ? C1 N1 C5 123.2(3) . . ? C1 N1 C2 120.4(3) . . ? C5 N1 C2 116.1(3) . . ? C3 C2 N1 111.6(4) . . ? C3 C2 H2A 109.3 . . ? N1 C2 H2A 109.3 . . ? C3 C2 H2B 109.3 . . ? N1 C2 H2B 109.3 . . ? H2A C2 H2B 108.0 . . ? C2 C3 C4 110.6(4) . . ? C2 C3 H3A 109.5 . . ? C4 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? C4 C3 H3B 109.5 . . ? H3A C3 H3B 108.1 . . ? N2 C4 C3 110.5(3) . . ? N2 C4 H4A 109.6 . . ? C3 C4 H4A 109.6 . . ? N2 C4 H4B 109.6 . . ? C3 C4 H4B 109.6 . . ? H4A C4 H4B 108.1 . . ? C1 N2 C17 122.9(3) . . ? C1 N2 C4 122.0(3) . . ? C17 N2 C4 114.5(3) . . ? N1 C5 C6 111.0(3) . . ? N1 C5 H5A 109.4 . . ? C6 C5 H5A 109.4 . . ? N1 C5 H5B 109.4 . . ? C6 C5 H5B 109.4 . . ? H5A C5 H5B 108.0 . . ? C5 C6 C7 113.1(3) . . ? C5 C6 H6A 109.0 . . ? C7 C6 H6A 109.0 . . ? C5 C6 H6B 109.0 . . ? C7 C6 H6B 109.0 . . ? H6A C6 H6B 107.8 . . ? C8 C7 C6 110.5(3) . . ? C8 C7 H7A 109.5 . . ? C6 C7 H7A 109.5 . . ? C8 C7 H7B 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 108.1 . . ? C7 C8 C9 115.6(3) . . ? C7 C8 H8A 108.4 . . ? C9 C8 H8A 108.4 . . ? C7 C8 H8B 108.4 . . ? C9 C8 H8B 108.4 . . ? H8A C8 H8B 107.4 . . ? C8 C9 C10 111.5(3) . . ? C8 C9 H9A 109.3 . . ? C10 C9 H9A 109.3 . . ? C8 C9 H9B 109.3 . . ? C10 C9 H9B 109.3 . . ? H9A C9 H9B 108.0 . . ? C11 C10 C9 114.8(3) . . ? C11 C10 H10A 108.6 . . ? C9 C10 H10A 108.6 . . ? C11 C10 H10B 108.6 . . ? C9 C10 H10B 108.6 . . ? H10A C10 H10B 107.5 . . ? C12 C11 C10 112.6(3) . . ? C12 C11 H11A 109.1 . . ? C10 C11 H11A 109.1 . . ? C12 C11 H11B 109.1 . . ? C10 C11 H11B 109.1 . . ? H11A C11 H11B 107.8 . . ? C11 C12 C13 114.3(3) . . ? C11 C12 H12A 108.7 . . ? C13 C12 H12A 108.7 . . ? C11 C12 H12B 108.7 . . ? C13 C12 H12B 108.7 . . ? H12A C12 H12B 107.6 . . ? C14 C13 C12 113.4(3) . . ? C14 C13 H13A 108.9 . . ? C12 C13 H13A 108.9 . . ? C14 C13 H13B 108.9 . . ? C12 C13 H13B 108.9 . . ? H13A C13 H13B 107.7 . . ? C13 C14 C15 114.0(3) . . ? C13 C14 H14A 108.8 . . ? C15 C14 H14A 108.8 . . ? C13 C14 H14B 108.8 . . ? C15 C14 H14B 108.8 . . ? H14A C14 H14B 107.7 . . ? C16 C15 C14 113.1(3) . . ? C16 C15 H15A 109.0 . . ? C14 C15 H15A 109.0 . . ? C16 C15 H15B 109.0 . . ? C14 C15 H15B 109.0 . . ? H15A C15 H15B 107.8 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N2 C17 H17A 109.5 . . ? N2 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? N2 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C19 C18 C23 121.2(3) . . ? C19 C18 C1 119.7(3) . . ? C23 C18 C1 119.1(3) . . ? C18 C19 C20 119.6(3) . . ? C18 C19 H19 120.2 . . ? C20 C19 H19 120.2 . . ? C21 C20 C19 119.0(3) . . ? C21 C20 H20 120.5 . . ? C19 C20 H20 120.5 . . ? C22 C21 C20 121.2(3) . . ? C22 C21 C24 119.0(3) . . ? C20 C21 C24 119.8(3) . . ? C23 C22 C21 119.6(3) . . ? C23 C22 H22 120.2 . . ? C21 C22 H22 120.2 . . ? C22 C23 C18 119.4(3) . . ? C22 C23 H23 120.3 . . ? C18 C23 H23 120.3 . . ? N4 C24 N3 122.2(3) . . ? N4 C24 C21 118.3(3) . . ? N3 C24 C21 119.5(3) . . ? C24 N3 C25 121.4(3) . . ? C24 N3 C28 122.6(3) . . ? C25 N3 C28 115.9(3) . . ? N3 C25 C26 110.5(3) . . ? N3 C25 H25A 109.5 . . ? C26 C25 H25A 109.5 . . ? N3 C25 H25B 109.5 . . ? C26 C25 H25B 109.5 . . ? H25A C25 H25B 108.1 . . ? C25 C26 C27 109.8(3) . . ? C25 C26 H26A 109.7 . . ? C27 C26 H26A 109.7 . . ? C25 C26 H26B 109.7 . . ? C27 C26 H26B 109.7 . . ? H26A C26 H26B 108.2 . . ? N4 C27 C26 111.0(3) . . ? N4 C27 H27A 109.4 . . ? C26 C27 H27A 109.4 . . ? N4 C27 H27B 109.4 . . ? C26 C27 H27B 109.4 . . ? H27A C27 H27B 108.0 . . ? C24 N4 C40 122.2(3) . . ? C24 N4 C27 122.0(3) . . ? C40 N4 C27 115.7(3) . . ? C29A C28 N3 117.6(7) . . ? N3 C28 C29 109.6(5) . . ? C29A C28 H28A 107.9 . . ? N3 C28 H28A 107.9 . . ? C29 C28 H28A 126.0 . . ? C29A C28 H28B 107.9 . . ? N3 C28 H28B 107.9 . . ? C29 C28 H28B 96.6 . . ? H28A C28 H28B 107.2 . . ? C30 C29 C28 106.6(7) . . ? C30 C29 H29A 110.4 . . ? C28 C29 H29A 110.4 . . ? C30 C29 H29B 110.4 . . ? C28 C29 H29B 110.4 . . ? H29A C29 H29B 108.6 . . ? C30 C29A C28 127.2(12) . . ? C30 C29A H29C 105.5 . . ? C28 C29A H29C 105.5 . . ? C30 C29A H29D 105.5 . . ? C28 C29A H29D 105.5 . . ? H29C C29A H29D 106.1 . . ? C31A C30 C29A 133.8(11) . . ? C29A C30 C31 123.6(8) . . ? C31A C30 C29 126.4(8) . . ? C31 C30 C29 110.1(6) . . ? C32 C31 C30 111.3(7) . . ? C32 C31 H31A 109.4 . . ? C30 C31 H31A 109.4 . . ? C32 C31 H31B 109.4 . . ? C30 C31 H31B 109.4 . . ? H31A C31 H31B 108.0 . . ? C30 C31A C32 139.1(13) . . ? C30 C31A H31C 102.3 . . ? C32 C31A H31C 102.3 . . ? C30 C31A H31D 102.3 . . ? C32 C31A H31D 102.3 . . ? H31C C31A H31D 104.9 . . ? C33A C32 C31A 140.6(11) . . ? C33A C32 C31 131.0(8) . . ? C31A C32 C33 131.0(8) . . ? C31 C32 C33 112.9(6) . . ? C34 C33 C32 112.7(7) . . ? C34 C33 H33A 109.1 . . ? C32 C33 H33A 109.1 . . ? C34 C33 H33B 109.1 . . ? C32 C33 H33B 109.1 . . ? H33A C33 H33B 107.8 . . ? C32 C33A C34 142.2(14) . . ? C32 C33A H33C 101.4 . . ? C34 C33A H33C 101.4 . . ? C32 C33A H33D 101.4 . . ? C34 C33A H33D 101.4 . . ? H33C C33A H33D 104.6 . . ? C35A C34 C33A 141.4(11) . . ? C35A C34 C33 131.8(8) . . ? C33A C34 C35 134.2(8) . . ? C33 C34 C35 114.5(6) . . ? C34 C35A C36 140.6(14) . . ? C34 C35A H35A 101.9 . . ? C36 C35A H35A 101.9 . . ? C34 C35A H35B 101.9 . . ? C36 C35A H35B 101.9 . . ? H35A C35A H35B 104.7 . . ? C36 C35 C34 114.3(7) . . ? C36 C35 H35C 108.7 . . ? C34 C35 H35C 108.7 . . ? C36 C35 H35D 108.7 . . ? C34 C35 H35D 108.7 . . ? H35C C35 H35D 107.6 . . ? C37A C36 C35A 138.8(12) . . ? C35A C36 C37 134.5(8) . . ? C37A C36 C35 130.1(8) . . ? C37 C36 C35 116.5(7) . . ? C38 C37 C36 118.5(8) . . ? C38 C37 H37A 107.7 . . ? C36 C37 H37A 107.7 . . ? C38 C37 H37B 107.7 . . ? C36 C37 H37B 107.7 . . ? H37A C37 H37B 107.1 . . ? C36 C37A C38 137.5(14) . . ? C36 C37A H37C 102.7 . . ? C38 C37A H37C 102.7 . . ? C36 C37A H37D 102.7 . . ? C38 C37A H37D 102.7 . . ? H37C C37A H37D 105.0 . . ? C37A C38 C39 134.1(8) . . ? C39 C38 C37 123.4(6) . . ? C38 C39 H39A 109.5 . . ? C38 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? C38 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? N4 C40 H40A 109.5 . . ? N4 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? N4 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 30.38 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 1.797 _refine_diff_density_min -2.125 _refine_diff_density_rms 0.113