# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_za _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C29 H33 N3 O' _chemical_formula_sum 'C29 H33 N3 O' _chemical_formula_weight 439.58 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P b c a' _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 13.8234(14) _cell_length_b 14.4667(14) _cell_length_c 24.486(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4896.6(8) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 158 _cell_measurement_theta_min 3 _cell_measurement_theta_max 26 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.193 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1888 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.925 _exptl_absorpt_correction_T_max 0.965 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1998a)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 'Bruker SMART 1000 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 39680 _diffrn_reflns_av_R_equivalents 0.0810 _diffrn_reflns_av_sigmaI/netI 0.0513 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4770 _reflns_number_gt 2860 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 1998b)' _computing_cell_refinement 'SAINTPlus (Bruker, 1998a)' _computing_data_reduction 'SAINTPlus (Bruker, 1998a)' _computing_structure_solution 'SHELXTL ver. 5.1 (Sheldrick, 1998b)' _computing_structure_refinement 'SHELXTL ver. 5.1 (Sheldrick, 1998b)' _computing_molecular_graphics 'SHELXTL ver. 5.1 (Sheldrick, 1998b)' _computing_publication_material 'SHELXTL ver. 5.1 (Sheldrick, 1998b)' _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^)+(0.0356P)^2^+3.2620P] 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 4770 _refine_ls_number_parameters 304 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0982 _refine_ls_R_factor_gt 0.0495 _refine_ls_wR_factor_ref 0.1239 _refine_ls_wR_factor_gt 0.1019 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _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 O1 O 0.29461(10) 0.17951(10) 0.63930(6) 0.0342(4) Uani 1 1 d . . . H1O H 0.2630 0.1230 0.6443 0.041 Uiso 1 1 d R . . N1 N 0.48458(13) 0.16834(12) 0.56667(8) 0.0339(5) Uani 1 1 d . . . N2 N 0.53985(14) 0.30404(13) 0.48796(8) 0.0367(5) Uani 1 1 d . . . N3 N 0.25864(14) 0.00026(13) 0.65437(8) 0.0381(5) Uani 1 1 d . . . C1 C 0.49243(15) 0.24566(15) 0.60205(9) 0.0295(5) Uani 1 1 d . . . C2 C 0.45013(15) 0.24374(14) 0.65376(9) 0.0281(5) Uani 1 1 d . . . C3 C 0.47394(15) 0.31382(15) 0.69185(9) 0.0309(5) Uani 1 1 d . . . H3A H 0.4410 0.3163 0.7249 0.037 Uiso 1 1 calc R . . C4 C 0.54388(16) 0.37780(15) 0.68122(9) 0.0321(5) Uani 1 1 d . . . H4A H 0.5614 0.4198 0.7082 0.038 Uiso 1 1 calc R . . C5 C 0.58973(15) 0.38117(14) 0.63023(9) 0.0302(5) Uani 1 1 d . . . C6 C 0.67018(16) 0.44017(15) 0.62061(10) 0.0364(6) Uani 1 1 d . . . H6A H 0.6939 0.4769 0.6488 0.044 Uiso 1 1 calc R . . C7 C 0.71259(17) 0.44328(17) 0.57084(11) 0.0415(6) Uani 1 1 d . . . H7A H 0.7693 0.4768 0.5659 0.050 Uiso 1 1 calc R . . C8 C 0.67099(17) 0.39581(16) 0.52647(10) 0.0400(6) Uani 1 1 d . . . H8A H 0.6976 0.4028 0.4918 0.048 Uiso 1 1 calc R . . C9 C 0.59178(16) 0.33935(15) 0.53326(9) 0.0334(5) Uani 1 1 d . . . C10 C 0.55651(15) 0.32121(14) 0.58776(9) 0.0296(5) Uani 1 1 d . . . C11 C 0.39969(18) 0.14464(17) 0.53590(10) 0.0441(6) Uani 1 1 d . . . H11A H 0.3475 0.1848 0.5461 0.066 Uiso 1 1 calc R . . H11B H 0.3821 0.0817 0.5434 0.066 Uiso 1 1 calc R . . H11C H 0.4128 0.1515 0.4976 0.066 Uiso 1 1 calc R . . C12 C 0.57219(17) 0.12486(17) 0.54689(10) 0.0418(6) Uani 1 1 d . . . H12A H 0.6261 0.1448 0.5686 0.063 Uiso 1 1 calc R . . H12B H 0.5827 0.1420 0.5095 0.063 Uiso 1 1 calc R . . H12C H 0.5659 0.0589 0.5495 0.063 Uiso 1 1 calc R . . C13 C 0.44311(18) 0.34456(19) 0.48296(10) 0.0460(6) Uani 1 1 d . . . H13A H 0.4114 0.3431 0.5178 0.069 Uiso 1 1 calc R . . H13B H 0.4060 0.3097 0.4570 0.069 Uiso 1 1 calc R . . H13C H 0.4486 0.4074 0.4708 0.069 Uiso 1 1 calc R . . C14 C 0.58959(19) 0.30586(19) 0.43579(10) 0.0482(7) Uani 1 1 d . . . H14A H 0.6521 0.2777 0.4396 0.072 Uiso 1 1 calc R . . H14B H 0.5972 0.3687 0.4240 0.072 Uiso 1 1 calc R . . H14C H 0.5524 0.2724 0.4092 0.072 Uiso 1 1 calc R . . C15 C 0.37913(15) 0.16619(14) 0.67133(9) 0.0293(5) Uani 1 1 d . . . C16 C 0.42204(16) 0.06812(14) 0.66389(9) 0.0292(5) Uani 1 1 d . . . C17 C 0.36301(17) -0.01002(15) 0.65753(9) 0.0330(5) Uani 1 1 d . . . C18 C 0.40528(18) -0.09797(15) 0.65548(10) 0.0398(6) Uani 1 1 d . . . H18A H 0.3661 -0.1496 0.6505 0.048 Uiso 1 1 calc R . . C19 C 0.50322(18) -0.10940(16) 0.66062(10) 0.0417(6) Uani 1 1 d . . . H19A H 0.5300 -0.1683 0.6593 0.050 Uiso 1 1 calc R . . C20 C 0.56198(18) -0.03336(16) 0.66769(9) 0.0390(6) Uani 1 1 d . . . H20A H 0.6285 -0.0407 0.6713 0.047 Uiso 1 1 calc R . . C21 C 0.52128(16) 0.05415(15) 0.66933(9) 0.0344(5) Uani 1 1 d . . . H21A H 0.5614 0.1051 0.6742 0.041 Uiso 1 1 calc R . . C22 C 0.21351(19) -0.05595(18) 0.61123(11) 0.0481(7) Uani 1 1 d . . . H22A H 0.2457 -0.0446 0.5771 0.072 Uiso 1 1 calc R . . H22B H 0.1464 -0.0397 0.6080 0.072 Uiso 1 1 calc R . . H22C H 0.2190 -0.1202 0.6204 0.072 Uiso 1 1 calc R . . C23 C 0.21335(18) -0.01892(17) 0.70754(11) 0.0461(7) Uani 1 1 d . . . H23A H 0.2437 0.0181 0.7352 0.069 Uiso 1 1 calc R . . H23B H 0.2211 -0.0832 0.7163 0.069 Uiso 1 1 calc R . . H23C H 0.1457 -0.0043 0.7058 0.069 Uiso 1 1 calc R . . C24 C 0.35257(16) 0.17468(14) 0.73253(9) 0.0307(5) Uani 1 1 d . . . C25 C 0.41426(17) 0.14431(15) 0.77397(9) 0.0348(5) Uani 1 1 d . . . H25A H 0.4738 0.1187 0.7648 0.042 Uiso 1 1 calc R . . C26 C 0.38877(18) 0.15146(16) 0.82828(10) 0.0405(6) Uani 1 1 d . . . H26A H 0.4308 0.1304 0.8552 0.049 Uiso 1 1 calc R . . C27 C 0.30086(19) 0.18993(17) 0.84275(10) 0.0444(6) Uani 1 1 d . . . H27A H 0.2836 0.1951 0.8793 0.053 Uiso 1 1 calc R . . C28 C 0.23912(18) 0.22045(16) 0.80251(11) 0.0426(6) Uani 1 1 d . . . H28A H 0.1798 0.2462 0.8120 0.051 Uiso 1 1 calc R . . C29 C 0.26449(16) 0.21316(15) 0.74791(10) 0.0365(6) Uani 1 1 d . . . H29A H 0.2221 0.2343 0.7212 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 O1 0.0321(8) 0.0242(8) 0.0464(10) 0.0050(7) -0.0055(7) -0.0021(7) N1 0.0358(11) 0.0252(10) 0.0407(11) -0.0055(8) -0.0029(9) -0.0014(8) N2 0.0393(11) 0.0336(11) 0.0371(11) -0.0003(9) 0.0021(9) -0.0005(9) N3 0.0356(11) 0.0277(10) 0.0510(12) 0.0004(9) -0.0034(10) -0.0061(9) C1 0.0283(11) 0.0219(11) 0.0383(13) -0.0038(9) -0.0042(10) 0.0021(9) C2 0.0277(11) 0.0193(11) 0.0373(13) -0.0003(9) -0.0025(10) 0.0010(9) C3 0.0324(12) 0.0235(11) 0.0367(13) 0.0005(9) 0.0021(10) 0.0024(10) C4 0.0353(13) 0.0205(11) 0.0404(14) -0.0049(9) -0.0047(11) 0.0009(10) C5 0.0281(12) 0.0206(11) 0.0418(14) -0.0011(9) -0.0020(10) 0.0029(9) C6 0.0347(13) 0.0243(12) 0.0503(15) -0.0023(11) -0.0034(11) -0.0021(10) C7 0.0321(13) 0.0327(13) 0.0596(17) -0.0003(12) 0.0044(12) -0.0090(11) C8 0.0378(14) 0.0353(14) 0.0468(16) 0.0014(11) 0.0072(12) -0.0006(11) C9 0.0325(12) 0.0265(12) 0.0411(14) -0.0015(10) 0.0004(10) 0.0023(10) C10 0.0258(11) 0.0238(11) 0.0393(13) -0.0010(9) -0.0021(10) 0.0018(9) C11 0.0467(15) 0.0416(15) 0.0439(15) -0.0060(12) -0.0044(12) -0.0077(12) C12 0.0471(15) 0.0313(13) 0.0471(15) -0.0063(11) 0.0000(12) 0.0044(11) C13 0.0461(15) 0.0512(17) 0.0405(15) 0.0025(12) -0.0031(12) 0.0023(13) C14 0.0543(16) 0.0451(16) 0.0452(15) -0.0067(12) 0.0069(13) -0.0030(13) C15 0.0280(11) 0.0213(11) 0.0384(13) -0.0001(9) -0.0017(10) 0.0006(9) C16 0.0349(13) 0.0233(11) 0.0295(12) 0.0005(9) 0.0003(10) -0.0001(9) C17 0.0391(13) 0.0246(12) 0.0355(13) 0.0006(10) -0.0002(10) -0.0018(10) C18 0.0476(15) 0.0246(12) 0.0473(15) -0.0013(10) -0.0020(12) -0.0032(11) C19 0.0547(17) 0.0247(12) 0.0458(15) -0.0017(11) -0.0014(12) 0.0077(11) C20 0.0387(14) 0.0360(14) 0.0424(15) 0.0007(11) -0.0013(11) 0.0096(11) C21 0.0358(13) 0.0258(12) 0.0415(14) 0.0009(10) -0.0009(11) 0.0004(10) C22 0.0479(16) 0.0374(15) 0.0591(17) 0.0026(13) -0.0089(13) -0.0114(12) C23 0.0425(15) 0.0338(14) 0.0619(18) -0.0004(12) 0.0060(13) -0.0068(11) C24 0.0328(12) 0.0170(10) 0.0425(14) -0.0007(9) 0.0023(10) -0.0030(9) C25 0.0374(13) 0.0240(12) 0.0428(14) -0.0002(10) 0.0029(11) -0.0008(10) C26 0.0521(16) 0.0297(13) 0.0398(15) 0.0014(11) -0.0012(12) -0.0074(11) C27 0.0566(17) 0.0360(14) 0.0407(15) -0.0057(12) 0.0087(13) -0.0114(13) C28 0.0391(14) 0.0303(13) 0.0584(17) -0.0064(12) 0.0138(13) -0.0029(11) C29 0.0364(13) 0.0254(12) 0.0476(15) -0.0009(10) 0.0033(11) 0.0019(10) _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 O1 C15 1.420(2) . ? O1 H1O 0.9349 . ? N1 C1 1.419(3) . ? N1 C11 1.436(3) . ? N1 C12 1.448(3) . ? N2 C9 1.416(3) . ? N2 C14 1.451(3) . ? N2 C13 1.465(3) . ? N3 C17 1.452(3) . ? N3 C23 1.471(3) . ? N3 C22 1.472(3) . ? C1 C2 1.395(3) . ? C1 C10 1.450(3) . ? C2 C3 1.416(3) . ? C2 C15 1.551(3) . ? C3 C4 1.363(3) . ? C3 H3A 0.9300 . ? C4 C5 1.401(3) . ? C4 H4A 0.9300 . ? C5 C6 1.422(3) . ? C5 C10 1.430(3) . ? C6 C7 1.353(3) . ? C6 H6A 0.9300 . ? C7 C8 1.408(3) . ? C7 H7A 0.9300 . ? C8 C9 1.376(3) . ? C8 H8A 0.9300 . ? C9 C10 1.445(3) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C24 1.548(3) . ? C15 C16 1.548(3) . ? C16 C21 1.393(3) . ? C16 C17 1.403(3) . ? C17 C18 1.401(3) . ? C18 C19 1.370(3) . ? C18 H18A 0.9300 . ? C19 C20 1.378(3) . ? C19 H19A 0.9300 . ? C20 C21 1.386(3) . ? C20 H20A 0.9300 . ? C21 H21A 0.9300 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 C29 1.391(3) . ? C24 C25 1.396(3) . ? C25 C26 1.379(3) . ? C25 H25A 0.9300 . ? C26 C27 1.383(3) . ? C26 H26A 0.9300 . ? C27 C28 1.376(4) . ? C27 H27A 0.9300 . ? C28 C29 1.386(3) . ? C28 H28A 0.9300 . ? C29 H29A 0.9300 . ? 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 C15 O1 H1O 101.2 . . ? C1 N1 C11 124.83(19) . . ? C1 N1 C12 118.85(18) . . ? C11 N1 C12 113.84(18) . . ? C9 N2 C14 116.28(19) . . ? C9 N2 C13 112.57(19) . . ? C14 N2 C13 110.59(19) . . ? C17 N3 C23 110.87(19) . . ? C17 N3 C22 113.76(19) . . ? C23 N3 C22 110.52(19) . . ? C2 C1 N1 120.43(19) . . ? C2 C1 C10 119.35(19) . . ? N1 C1 C10 119.58(19) . . ? C1 C2 C3 119.08(19) . . ? C1 C2 C15 122.09(18) . . ? C3 C2 C15 118.82(19) . . ? C4 C3 C2 121.7(2) . . ? C4 C3 H3A 119.2 . . ? C2 C3 H3A 119.2 . . ? C3 C4 C5 121.0(2) . . ? C3 C4 H4A 119.5 . . ? C5 C4 H4A 119.5 . . ? C4 C5 C6 121.5(2) . . ? C4 C5 C10 118.8(2) . . ? C6 C5 C10 119.7(2) . . ? C7 C6 C5 120.5(2) . . ? C7 C6 H6A 119.7 . . ? C5 C6 H6A 119.7 . . ? C6 C7 C8 120.1(2) . . ? C6 C7 H7A 119.9 . . ? C8 C7 H7A 119.9 . . ? C9 C8 C7 121.4(2) . . ? C9 C8 H8A 119.3 . . ? C7 C8 H8A 119.3 . . ? C8 C9 N2 121.5(2) . . ? C8 C9 C10 119.2(2) . . ? N2 C9 C10 119.12(19) . . ? C5 C10 C9 116.95(19) . . ? C5 C10 C1 118.56(19) . . ? C9 C10 C1 124.47(19) . . ? N1 C11 H11A 109.5 . . ? N1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? 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 . . ? N2 C13 H13A 109.5 . . ? N2 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N2 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N2 C14 H14A 109.5 . . ? N2 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N2 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O1 C15 C24 109.20(17) . . ? O1 C15 C16 111.98(17) . . ? C24 C15 C16 106.11(16) . . ? O1 C15 C2 105.61(16) . . ? C24 C15 C2 111.17(17) . . ? C16 C15 C2 112.81(17) . . ? C21 C16 C17 117.8(2) . . ? C21 C16 C15 119.93(19) . . ? C17 C16 C15 121.91(19) . . ? C18 C17 C16 119.6(2) . . ? C18 C17 N3 120.3(2) . . ? C16 C17 N3 120.08(19) . . ? C19 C18 C17 121.2(2) . . ? C19 C18 H18A 119.4 . . ? C17 C18 H18A 119.4 . . ? C18 C19 C20 119.8(2) . . ? C18 C19 H19A 120.1 . . ? C20 C19 H19A 120.1 . . ? C19 C20 C21 119.6(2) . . ? C19 C20 H20A 120.2 . . ? C21 C20 H20A 120.2 . . ? C20 C21 C16 122.0(2) . . ? C20 C21 H21A 119.0 . . ? C16 C21 H21A 119.0 . . ? N3 C22 H22A 109.5 . . ? N3 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? N3 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? N3 C23 H23A 109.5 . . ? N3 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? N3 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C29 C24 C25 117.6(2) . . ? C29 C24 C15 120.1(2) . . ? C25 C24 C15 122.26(19) . . ? C26 C25 C24 121.4(2) . . ? C26 C25 H25A 119.3 . . ? C24 C25 H25A 119.3 . . ? C25 C26 C27 120.1(2) . . ? C25 C26 H26A 119.9 . . ? C27 C26 H26A 119.9 . . ? C28 C27 C26 119.4(2) . . ? C28 C27 H27A 120.3 . . ? C26 C27 H27A 120.3 . . ? C27 C28 C29 120.6(2) . . ? C27 C28 H28A 119.7 . . ? C29 C28 H28A 119.7 . . ? C28 C29 C24 120.9(2) . . ? C28 C29 H29A 119.6 . . ? C24 C29 H29A 119.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 N1 C1 C2 76.9(3) . . . . ? C12 N1 C1 C2 -122.1(2) . . . . ? C11 N1 C1 C10 -112.3(2) . . . . ? C12 N1 C1 C10 48.7(3) . . . . ? N1 C1 C2 C3 168.30(19) . . . . ? C10 C1 C2 C3 -2.5(3) . . . . ? N1 C1 C2 C15 -10.6(3) . . . . ? C10 C1 C2 C15 178.63(18) . . . . ? C1 C2 C3 C4 -6.4(3) . . . . ? C15 C2 C3 C4 172.49(19) . . . . ? C2 C3 C4 C5 5.2(3) . . . . ? C3 C4 C5 C6 -172.6(2) . . . . ? C3 C4 C5 C10 5.1(3) . . . . ? C4 C5 C6 C7 -179.1(2) . . . . ? C10 C5 C6 C7 3.2(3) . . . . ? C5 C6 C7 C8 7.0(3) . . . . ? C6 C7 C8 C9 -5.5(4) . . . . ? C7 C8 C9 N2 169.2(2) . . . . ? C7 C8 C9 C10 -6.2(3) . . . . ? C14 N2 C9 C8 18.4(3) . . . . ? C13 N2 C9 C8 -110.7(2) . . . . ? C14 N2 C9 C10 -166.3(2) . . . . ? C13 N2 C9 C10 64.7(3) . . . . ? C4 C5 C10 C9 167.88(19) . . . . ? C6 C5 C10 C9 -14.4(3) . . . . ? C4 C5 C10 C1 -13.6(3) . . . . ? C6 C5 C10 C1 164.1(2) . . . . ? C8 C9 C10 C5 15.8(3) . . . . ? N2 C9 C10 C5 -159.71(19) . . . . ? C8 C9 C10 C1 -162.6(2) . . . . ? N2 C9 C10 C1 21.9(3) . . . . ? C2 C1 C10 C5 12.4(3) . . . . ? N1 C1 C10 C5 -158.52(19) . . . . ? C2 C1 C10 C9 -169.3(2) . . . . ? N1 C1 C10 C9 19.8(3) . . . . ? C1 C2 C15 O1 -68.3(2) . . . . ? C3 C2 C15 O1 112.9(2) . . . . ? C1 C2 C15 C24 173.42(19) . . . . ? C3 C2 C15 C24 -5.4(3) . . . . ? C1 C2 C15 C16 54.4(3) . . . . ? C3 C2 C15 C16 -124.5(2) . . . . ? O1 C15 C16 C21 149.96(19) . . . . ? C24 C15 C16 C21 -91.0(2) . . . . ? C2 C15 C16 C21 31.0(3) . . . . ? O1 C15 C16 C17 -37.0(3) . . . . ? C24 C15 C16 C17 82.0(2) . . . . ? C2 C15 C16 C17 -156.0(2) . . . . ? C21 C16 C17 C18 -1.6(3) . . . . ? C15 C16 C17 C18 -174.7(2) . . . . ? C21 C16 C17 N3 177.0(2) . . . . ? C15 C16 C17 N3 3.9(3) . . . . ? C23 N3 C17 C18 79.9(3) . . . . ? C22 N3 C17 C18 -45.4(3) . . . . ? C23 N3 C17 C16 -98.7(2) . . . . ? C22 N3 C17 C16 136.0(2) . . . . ? C16 C17 C18 C19 1.3(4) . . . . ? N3 C17 C18 C19 -177.3(2) . . . . ? C17 C18 C19 C20 -0.3(4) . . . . ? C18 C19 C20 C21 -0.3(4) . . . . ? C19 C20 C21 C16 -0.1(4) . . . . ? C17 C16 C21 C20 1.1(3) . . . . ? C15 C16 C21 C20 174.4(2) . . . . ? O1 C15 C24 C29 -14.8(3) . . . . ? C16 C15 C24 C29 -135.7(2) . . . . ? C2 C15 C24 C29 101.3(2) . . . . ? O1 C15 C24 C25 164.83(18) . . . . ? C16 C15 C24 C25 44.0(3) . . . . ? C2 C15 C24 C25 -79.0(2) . . . . ? C29 C24 C25 C26 0.4(3) . . . . ? C15 C24 C25 C26 -179.2(2) . . . . ? C24 C25 C26 C27 -0.5(3) . . . . ? C25 C26 C27 C28 0.3(3) . . . . ? C26 C27 C28 C29 -0.2(3) . . . . ? C27 C28 C29 C24 0.2(3) . . . . ? C25 C24 C29 C28 -0.3(3) . . . . ? C15 C24 C29 C28 179.3(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag O1 H1O N3 1_555 0.935 1.794 2.666(4) 154 ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.199 _refine_diff_density_min -0.208 _refine_diff_density_rms 0.044 _database_code_depnum_ccdc_archive 'CCDC 956636' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_fin _vrf_PLAT353_fin ; PROBLEM: Long N-H Bond (0.87A) N1 - H1N and N2 - H1N RESPONSE: This intermolecular contact is normally observed interatomic distance for very short hydrogen bond (N1...N2 2.540(2)A). ; _vrf_PLAT771_fin ; PROBLEM: Suspect N-H Bond in CIF: N2 -- H1N RESPONSE: This intermolecular contact is normally observed interatomic distance for very short hydrogen bond (N1...N2 2.540(2)A). ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C29 H34 N3 O, Cl O4' _chemical_formula_sum 'C29 H34 Cl N3 O5' _chemical_formula_weight 540.04 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _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 21.5850(10) _cell_length_b 7.8022(4) _cell_length_c 15.6198(8) _cell_angle_alpha 90.00 _cell_angle_beta 95.6800(10) _cell_angle_gamma 90.00 _cell_volume 2617.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 646 _cell_measurement_theta_min 3 _cell_measurement_theta_max 29 _exptl_crystal_description plate _exptl_crystal_colour grey _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.370 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1144 _exptl_absorpt_coefficient_mu 0.192 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.919 _exptl_absorpt_correction_T_max 0.956 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX II CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 29499 _diffrn_reflns_av_R_equivalents 0.0347 _diffrn_reflns_av_sigmaI/netI 0.0297 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 29.00 _reflns_number_total 6966 _reflns_number_gt 5479 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX II' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement 'SHELXTL (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0505P)^2^+1.4318P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6966 _refine_ls_number_parameters 349 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0569 _refine_ls_R_factor_gt 0.0407 _refine_ls_wR_factor_ref 0.1104 _refine_ls_wR_factor_gt 0.1005 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.41115(6) 0.02803(17) 0.30959(9) 0.0221(3) Uani 1 1 d . . . H1N H 0.3570 -0.0196 0.2899 0.026 Uiso 1 1 d R . . N2 N 0.29483(5) -0.02536(15) 0.28178(7) 0.0160(2) Uani 1 1 d . . . N3 N 0.12338(6) 0.28326(16) 0.20439(8) 0.0192(2) Uani 1 1 d . . . O5 O 0.15969(4) -0.03058(13) 0.25730(6) 0.0154(2) Uani 1 1 d . . . H5O H 0.1555 0.0580 0.2272 0.018 Uiso 1 1 d R . . C1 C 0.39643(6) 0.18682(19) 0.35354(10) 0.0194(3) Uani 1 1 d . . . C2 C 0.44380(7) 0.2965(2) 0.38066(11) 0.0251(3) Uani 1 1 d . . . H2A H 0.4851 0.2707 0.3690 0.030 Uiso 1 1 calc R . . C3 C 0.43194(7) 0.4467(2) 0.42549(11) 0.0264(3) Uani 1 1 d . . . H3A H 0.4645 0.5262 0.4405 0.032 Uiso 1 1 calc R . . C4 C 0.37330(7) 0.4782(2) 0.44752(10) 0.0229(3) Uani 1 1 d . . . H4A H 0.3657 0.5770 0.4804 0.028 Uiso 1 1 calc R . . C5 C 0.32367(6) 0.36454(18) 0.42166(9) 0.0176(3) Uani 1 1 d . . . C6 C 0.26374(7) 0.39476(19) 0.44750(9) 0.0187(3) Uani 1 1 d . . . H6A H 0.2570 0.4906 0.4829 0.022 Uiso 1 1 calc R . . C7 C 0.21539(6) 0.28768(18) 0.42205(9) 0.0165(3) Uani 1 1 d . . . H7A H 0.1761 0.3081 0.4428 0.020 Uiso 1 1 calc R . . C8 C 0.22148(6) 0.14673(17) 0.36574(8) 0.0134(2) Uani 1 1 d . . . C9 C 0.28016(6) 0.11218(17) 0.33966(8) 0.0141(2) Uani 1 1 d . . . C10 C 0.33312(6) 0.21800(18) 0.36998(9) 0.0159(3) Uani 1 1 d . . . C11 C 0.44274(8) -0.0999(2) 0.37009(13) 0.0324(4) Uani 1 1 d . . . H11A H 0.4188 -0.1142 0.4197 0.049 Uiso 1 1 calc R . . H11B H 0.4847 -0.0594 0.3897 0.049 Uiso 1 1 calc R . . H11C H 0.4454 -0.2100 0.3406 0.049 Uiso 1 1 calc R . . C12 C 0.44578(8) 0.0556(2) 0.23253(12) 0.0322(4) Uani 1 1 d . . . H12A H 0.4260 0.1482 0.1973 0.048 Uiso 1 1 calc R . . H12B H 0.4451 -0.0501 0.1985 0.048 Uiso 1 1 calc R . . H12C H 0.4890 0.0867 0.2512 0.048 Uiso 1 1 calc R . . C13 C 0.27914(7) -0.20355(18) 0.30426(10) 0.0195(3) Uani 1 1 d . . . H13A H 0.2871 -0.2195 0.3666 0.029 Uiso 1 1 calc R . . H13B H 0.3049 -0.2836 0.2749 0.029 Uiso 1 1 calc R . . H13C H 0.2351 -0.2254 0.2862 0.029 Uiso 1 1 calc R . . C14 C 0.28373(7) 0.0178(2) 0.18892(9) 0.0213(3) Uani 1 1 d . . . H14A H 0.2976 0.1353 0.1797 0.032 Uiso 1 1 calc R . . H14B H 0.2392 0.0082 0.1702 0.032 Uiso 1 1 calc R . . H14C H 0.3070 -0.0617 0.1556 0.032 Uiso 1 1 calc R . . C15 C 0.16157(6) 0.04112(17) 0.34176(8) 0.0130(2) Uani 1 1 d . . . C16 C 0.10175(6) 0.15361(17) 0.34200(8) 0.0137(2) Uani 1 1 d . . . C17 C 0.06187(6) 0.13616(18) 0.40672(9) 0.0158(3) Uani 1 1 d . . . H17A H 0.0737 0.0630 0.4541 0.019 Uiso 1 1 calc R . . C18 C 0.00525(6) 0.22300(19) 0.40374(9) 0.0176(3) Uani 1 1 d . . . H18A H -0.0209 0.2093 0.4488 0.021 Uiso 1 1 calc R . . C19 C -0.01275(6) 0.32944(19) 0.33462(9) 0.0195(3) Uani 1 1 d . . . H19A H -0.0517 0.3870 0.3314 0.023 Uiso 1 1 calc R . . C20 C 0.02646(6) 0.35150(19) 0.27013(9) 0.0189(3) Uani 1 1 d . . . H20A H 0.0145 0.4262 0.2234 0.023 Uiso 1 1 calc R . . C21 C 0.08340(6) 0.26515(18) 0.27321(8) 0.0159(3) Uani 1 1 d . . . C22 C 0.16539(7) 0.4330(2) 0.21665(10) 0.0259(3) Uani 1 1 d . . . H22A H 0.1866 0.4314 0.2751 0.039 Uiso 1 1 calc R . . H22B H 0.1410 0.5387 0.2080 0.039 Uiso 1 1 calc R . . H22C H 0.1964 0.4282 0.1749 0.039 Uiso 1 1 calc R . . C23 C 0.08907(8) 0.2901(2) 0.11844(9) 0.0256(3) Uani 1 1 d . . . H23A H 0.0593 0.1949 0.1119 0.038 Uiso 1 1 calc R . . H23B H 0.1184 0.2808 0.0746 0.038 Uiso 1 1 calc R . . H23C H 0.0666 0.3990 0.1114 0.038 Uiso 1 1 calc R . . C24 C 0.15785(6) -0.10787(17) 0.40538(8) 0.0142(3) Uani 1 1 d . . . C25 C 0.18999(6) -0.10475(18) 0.48714(9) 0.0164(3) Uani 1 1 d . . . H25A H 0.2180 -0.0135 0.5029 0.020 Uiso 1 1 calc R . . C26 C 0.18135(7) -0.23480(19) 0.54616(9) 0.0191(3) Uani 1 1 d . . . H26A H 0.2035 -0.2317 0.6018 0.023 Uiso 1 1 calc R . . C27 C 0.14062(7) -0.36829(19) 0.52385(9) 0.0194(3) Uani 1 1 d . . . H27A H 0.1343 -0.4558 0.5644 0.023 Uiso 1 1 calc R . . C28 C 0.10897(7) -0.37372(19) 0.44178(9) 0.0193(3) Uani 1 1 d . . . H28A H 0.0815 -0.4660 0.4260 0.023 Uiso 1 1 calc R . . C29 C 0.11746(6) -0.24452(18) 0.38280(9) 0.0172(3) Uani 1 1 d . . . H29A H 0.0958 -0.2490 0.3269 0.021 Uiso 1 1 calc R . . Cl1 Cl 0.363818(16) -0.45723(5) 0.11285(2) 0.02313(9) Uani 1 1 d . . . O1 O 0.30997(6) -0.5174(2) 0.15040(9) 0.0448(4) Uani 1 1 d . . . O2 O 0.39982(6) -0.3469(2) 0.17247(11) 0.0508(4) Uani 1 1 d . . . O3 O 0.34349(7) -0.3630(2) 0.03637(11) 0.0598(5) Uani 1 1 d . . . O4 O 0.40086(7) -0.5986(2) 0.09071(11) 0.0505(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0158(6) 0.0183(6) 0.0334(7) 0.0018(5) 0.0093(5) 0.0004(5) N2 0.0164(5) 0.0138(6) 0.0186(6) -0.0012(4) 0.0047(4) 0.0003(4) N3 0.0205(6) 0.0208(6) 0.0169(6) 0.0046(5) 0.0051(4) 0.0031(5) O5 0.0170(4) 0.0161(5) 0.0131(4) -0.0013(4) 0.0014(3) 0.0003(4) C1 0.0150(6) 0.0167(7) 0.0270(7) 0.0028(6) 0.0048(5) -0.0003(5) C2 0.0145(6) 0.0253(8) 0.0356(8) 0.0042(7) 0.0025(6) -0.0032(6) C3 0.0190(7) 0.0235(8) 0.0357(9) 0.0025(7) -0.0025(6) -0.0083(6) C4 0.0231(7) 0.0176(7) 0.0271(7) -0.0010(6) -0.0028(6) -0.0040(6) C5 0.0176(6) 0.0151(7) 0.0197(6) 0.0012(5) -0.0006(5) -0.0008(5) C6 0.0204(7) 0.0151(7) 0.0204(7) -0.0032(5) 0.0012(5) 0.0003(5) C7 0.0157(6) 0.0159(7) 0.0182(6) -0.0018(5) 0.0023(5) 0.0013(5) C8 0.0134(6) 0.0121(6) 0.0146(6) 0.0018(5) 0.0009(4) -0.0001(5) C9 0.0151(6) 0.0116(6) 0.0156(6) 0.0015(5) 0.0018(5) 0.0005(5) C10 0.0141(6) 0.0135(6) 0.0204(6) 0.0030(5) 0.0021(5) -0.0008(5) C11 0.0230(8) 0.0243(8) 0.0499(11) 0.0071(8) 0.0037(7) 0.0058(6) C12 0.0250(8) 0.0311(9) 0.0437(10) -0.0033(7) 0.0197(7) -0.0046(7) C13 0.0187(7) 0.0130(6) 0.0277(7) -0.0004(5) 0.0058(5) 0.0012(5) C14 0.0229(7) 0.0231(8) 0.0186(7) -0.0015(6) 0.0063(5) -0.0002(6) C15 0.0122(6) 0.0132(6) 0.0136(6) -0.0011(5) 0.0015(4) 0.0000(5) C16 0.0120(6) 0.0127(6) 0.0161(6) -0.0015(5) -0.0001(5) -0.0005(5) C17 0.0161(6) 0.0156(6) 0.0156(6) 0.0000(5) 0.0012(5) -0.0003(5) C18 0.0155(6) 0.0181(7) 0.0198(6) -0.0031(5) 0.0046(5) -0.0017(5) C19 0.0143(6) 0.0196(7) 0.0246(7) -0.0036(6) 0.0012(5) 0.0031(5) C20 0.0184(6) 0.0185(7) 0.0192(6) 0.0017(5) -0.0016(5) 0.0033(5) C21 0.0156(6) 0.0161(7) 0.0161(6) -0.0001(5) 0.0021(5) 0.0004(5) C22 0.0248(7) 0.0284(8) 0.0255(7) 0.0083(6) 0.0074(6) -0.0028(6) C23 0.0344(8) 0.0255(8) 0.0174(7) 0.0025(6) 0.0043(6) 0.0086(7) C24 0.0129(6) 0.0135(6) 0.0164(6) 0.0000(5) 0.0033(5) 0.0022(5) C25 0.0158(6) 0.0152(6) 0.0179(6) -0.0008(5) 0.0011(5) 0.0016(5) C26 0.0227(7) 0.0179(7) 0.0170(6) 0.0004(5) 0.0027(5) 0.0046(5) C27 0.0221(7) 0.0155(7) 0.0220(7) 0.0034(5) 0.0087(5) 0.0036(5) C28 0.0175(6) 0.0144(7) 0.0267(7) -0.0001(5) 0.0051(5) -0.0009(5) C29 0.0159(6) 0.0164(7) 0.0194(6) -0.0011(5) 0.0011(5) 0.0011(5) Cl1 0.01845(16) 0.02096(18) 0.03067(19) 0.00177(14) 0.00583(13) 0.00072(13) O1 0.0349(7) 0.0555(9) 0.0468(8) -0.0025(7) 0.0182(6) -0.0176(7) O2 0.0334(7) 0.0509(9) 0.0679(10) -0.0259(8) 0.0044(7) -0.0123(7) O3 0.0476(9) 0.0661(11) 0.0644(10) 0.0392(9) -0.0012(7) -0.0008(8) O4 0.0378(8) 0.0413(8) 0.0718(11) -0.0160(8) 0.0020(7) 0.0168(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.4664(19) . ? N1 C11 1.492(2) . ? N1 C12 1.494(2) . ? N1 H1N 1.2362 . ? N2 C9 1.4580(17) . ? N2 C13 1.4814(18) . ? N2 C14 1.4851(18) . ? N2 H1N 1.3361 . ? N3 C21 1.4505(17) . ? N3 C23 1.4685(19) . ? N3 C22 1.480(2) . ? O5 C15 1.4298(15) . ? O5 H5O 0.8355 . ? C1 C2 1.368(2) . ? C1 C10 1.4360(19) . ? C2 C3 1.401(2) . ? C2 H2A 0.9500 . ? C3 C4 1.366(2) . ? C3 H3A 0.9500 . ? C4 C5 1.418(2) . ? C4 H4A 0.9500 . ? C5 C6 1.4125(19) . ? C5 C10 1.426(2) . ? C6 C7 1.365(2) . ? C6 H6A 0.9500 . ? C7 C8 1.4225(19) . ? C7 H7A 0.9500 . ? C8 C9 1.3946(18) . ? C8 C15 1.5479(18) . ? C9 C10 1.4510(19) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C24 1.5366(18) . ? C15 C16 1.5615(18) . ? C16 C17 1.3977(18) . ? C16 C21 1.4087(18) . ? C17 C18 1.3942(19) . ? C17 H17A 0.9500 . ? C18 C19 1.387(2) . ? C18 H18A 0.9500 . ? C19 C20 1.389(2) . ? C19 H19A 0.9500 . ? C20 C21 1.3981(19) . ? C20 H20A 0.9500 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 C25 1.3920(18) . ? C24 C29 1.4000(19) . ? C25 C26 1.396(2) . ? C25 H25A 0.9500 . ? C26 C27 1.385(2) . ? C26 H26A 0.9500 . ? C27 C28 1.392(2) . ? C27 H27A 0.9500 . ? C28 C29 1.390(2) . ? C28 H28A 0.9500 . ? C29 H29A 0.9500 . ? Cl1 O4 1.4250(14) . ? Cl1 O1 1.4318(13) . ? Cl1 O3 1.4342(15) . ? Cl1 O2 1.4385(14) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C11 112.03(13) . . ? C1 N1 C12 113.86(12) . . ? C11 N1 C12 111.89(13) . . ? C1 N1 H1N 97.3 . . ? C11 N1 H1N 108.5 . . ? C12 N1 H1N 112.3 . . ? C9 N2 C13 118.36(11) . . ? C9 N2 C14 114.51(11) . . ? C13 N2 C14 115.19(11) . . ? C9 N2 H1N 101.2 . . ? C13 N2 H1N 105.1 . . ? C14 N2 H1N 98.5 . . ? C21 N3 C23 113.44(12) . . ? C21 N3 C22 112.51(12) . . ? C23 N3 C22 109.69(12) . . ? C15 O5 H5O 100.7 . . ? C2 C1 C10 122.27(14) . . ? C2 C1 N1 118.92(13) . . ? C10 C1 N1 118.75(12) . . ? C1 C2 C3 120.65(14) . . ? C1 C2 H2A 119.7 . . ? C3 C2 H2A 119.7 . . ? C4 C3 C2 119.72(14) . . ? C4 C3 H3A 120.1 . . ? C2 C3 H3A 120.1 . . ? C3 C4 C5 120.55(15) . . ? C3 C4 H4A 119.7 . . ? C5 C4 H4A 119.7 . . ? C6 C5 C4 120.11(13) . . ? C6 C5 C10 118.81(12) . . ? C4 C5 C10 121.08(13) . . ? C7 C6 C5 120.68(13) . . ? C7 C6 H6A 119.7 . . ? C5 C6 H6A 119.7 . . ? C6 C7 C8 122.57(13) . . ? C6 C7 H7A 118.7 . . ? C8 C7 H7A 118.7 . . ? C9 C8 C7 118.19(12) . . ? C9 C8 C15 125.99(12) . . ? C7 C8 C15 115.78(11) . . ? C8 C9 C10 120.24(12) . . ? C8 C9 N2 125.64(12) . . ? C10 C9 N2 114.12(11) . . ? C5 C10 C1 115.40(12) . . ? C5 C10 C9 119.27(12) . . ? C1 C10 C9 125.32(13) . . ? N1 C11 H11A 109.5 . . ? N1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? 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 . . ? N2 C13 H13A 109.5 . . ? N2 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N2 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N2 C14 H14A 109.5 . . ? N2 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N2 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O5 C15 C24 107.59(10) . . ? O5 C15 C8 112.23(10) . . ? C24 C15 C8 110.01(10) . . ? O5 C15 C16 105.91(10) . . ? C24 C15 C16 109.11(10) . . ? C8 C15 C16 111.81(11) . . ? C17 C16 C21 117.71(12) . . ? C17 C16 C15 121.03(12) . . ? C21 C16 C15 121.03(11) . . ? C18 C17 C16 121.94(13) . . ? C18 C17 H17A 119.0 . . ? C16 C17 H17A 119.0 . . ? C19 C18 C17 119.62(13) . . ? C19 C18 H18A 120.2 . . ? C17 C18 H18A 120.2 . . ? C18 C19 C20 119.66(13) . . ? C18 C19 H19A 120.2 . . ? C20 C19 H19A 120.2 . . ? C19 C20 C21 120.79(13) . . ? C19 C20 H20A 119.6 . . ? C21 C20 H20A 119.6 . . ? C20 C21 C16 120.25(12) . . ? C20 C21 N3 120.86(12) . . ? C16 C21 N3 118.85(12) . . ? N3 C22 H22A 109.5 . . ? N3 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? N3 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? N3 C23 H23A 109.5 . . ? N3 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? N3 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C25 C24 C29 119.06(13) . . ? C25 C24 C15 121.80(12) . . ? C29 C24 C15 118.97(12) . . ? C24 C25 C26 120.41(13) . . ? C24 C25 H25A 119.8 . . ? C26 C25 H25A 119.8 . . ? C27 C26 C25 120.23(13) . . ? C27 C26 H26A 119.9 . . ? C25 C26 H26A 119.9 . . ? C26 C27 C28 119.73(13) . . ? C26 C27 H27A 120.1 . . ? C28 C27 H27A 120.1 . . ? C29 C28 C27 120.21(13) . . ? C29 C28 H28A 119.9 . . ? C27 C28 H28A 119.9 . . ? C28 C29 C24 120.34(13) . . ? C28 C29 H29A 119.8 . . ? C24 C29 H29A 119.8 . . ? O4 Cl1 O1 110.09(10) . . ? O4 Cl1 O3 109.12(11) . . ? O1 Cl1 O3 108.38(9) . . ? O4 Cl1 O2 109.90(9) . . ? O1 Cl1 O2 109.85(9) . . ? O3 Cl1 O2 109.47(11) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 N1 C1 C2 72.82(17) . . . . ? C12 N1 C1 C2 -55.41(19) . . . . ? C11 N1 C1 C10 -104.46(15) . . . . ? C12 N1 C1 C10 127.31(15) . . . . ? C10 C1 C2 C3 -0.6(2) . . . . ? N1 C1 C2 C3 -177.81(14) . . . . ? C1 C2 C3 C4 4.5(2) . . . . ? C2 C3 C4 C5 -3.2(2) . . . . ? C3 C4 C5 C6 177.61(14) . . . . ? C3 C4 C5 C10 -2.0(2) . . . . ? C4 C5 C6 C7 179.09(14) . . . . ? C10 C5 C6 C7 -1.3(2) . . . . ? C5 C6 C7 C8 -3.1(2) . . . . ? C6 C7 C8 C9 3.6(2) . . . . ? C6 C7 C8 C15 -178.58(13) . . . . ? C7 C8 C9 C10 0.21(19) . . . . ? C15 C8 C9 C10 -177.37(12) . . . . ? C7 C8 C9 N2 -179.38(12) . . . . ? C15 C8 C9 N2 3.0(2) . . . . ? C13 N2 C9 C8 -55.98(18) . . . . ? C14 N2 C9 C8 85.06(16) . . . . ? C13 N2 C9 C10 124.40(13) . . . . ? C14 N2 C9 C10 -94.56(14) . . . . ? C6 C5 C10 C1 -174.08(13) . . . . ? C4 C5 C10 C1 5.5(2) . . . . ? C6 C5 C10 C9 4.9(2) . . . . ? C4 C5 C10 C9 -175.47(13) . . . . ? C2 C1 C10 C5 -4.3(2) . . . . ? N1 C1 C10 C5 172.93(12) . . . . ? C2 C1 C10 C9 176.79(14) . . . . ? N1 C1 C10 C9 -6.0(2) . . . . ? C8 C9 C10 C5 -4.40(19) . . . . ? N2 C9 C10 C5 175.24(12) . . . . ? C8 C9 C10 C1 174.51(13) . . . . ? N2 C9 C10 C1 -5.85(19) . . . . ? C9 C8 C15 O5 -33.61(18) . . . . ? C7 C8 C15 O5 148.75(11) . . . . ? C9 C8 C15 C24 86.14(15) . . . . ? C7 C8 C15 C24 -91.50(13) . . . . ? C9 C8 C15 C16 -152.46(13) . . . . ? C7 C8 C15 C16 29.90(15) . . . . ? O5 C15 C16 C17 129.54(12) . . . . ? C24 C15 C16 C17 13.99(16) . . . . ? C8 C15 C16 C17 -107.93(14) . . . . ? O5 C15 C16 C21 -44.92(16) . . . . ? C24 C15 C16 C21 -160.47(12) . . . . ? C8 C15 C16 C21 77.61(15) . . . . ? C21 C16 C17 C18 1.0(2) . . . . ? C15 C16 C17 C18 -173.64(12) . . . . ? C16 C17 C18 C19 0.4(2) . . . . ? C17 C18 C19 C20 -1.5(2) . . . . ? C18 C19 C20 C21 1.2(2) . . . . ? C19 C20 C21 C16 0.2(2) . . . . ? C19 C20 C21 N3 177.77(13) . . . . ? C17 C16 C21 C20 -1.3(2) . . . . ? C15 C16 C21 C20 173.36(12) . . . . ? C17 C16 C21 N3 -178.89(12) . . . . ? C15 C16 C21 N3 -4.26(19) . . . . ? C23 N3 C21 C20 -38.67(19) . . . . ? C22 N3 C21 C20 86.59(16) . . . . ? C23 N3 C21 C16 138.93(13) . . . . ? C22 N3 C21 C16 -95.81(15) . . . . ? O5 C15 C24 C25 144.57(12) . . . . ? C8 C15 C24 C25 22.04(16) . . . . ? C16 C15 C24 C25 -100.96(14) . . . . ? O5 C15 C24 C29 -40.22(15) . . . . ? C8 C15 C24 C29 -162.75(12) . . . . ? C16 C15 C24 C29 74.25(15) . . . . ? C29 C24 C25 C26 -0.9(2) . . . . ? C15 C24 C25 C26 174.27(12) . . . . ? C24 C25 C26 C27 0.0(2) . . . . ? C25 C26 C27 C28 1.0(2) . . . . ? C26 C27 C28 C29 -0.9(2) . . . . ? C27 C28 C29 C24 0.0(2) . . . . ? C25 C24 C29 C28 1.0(2) . . . . ? C15 C24 C29 C28 -174.38(12) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag N1 H1N N2 1_555 1.236 1.336 2.540(2) 162 ? O5 H5O N3 1_555 0.835 1.910 2.677(2) 152 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 29.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.429 _refine_diff_density_min -0.470 _refine_diff_density_rms 0.052 _database_code_depnum_ccdc_archive 'CCDC 956637' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_mo _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H19 N2, B F4' _chemical_formula_sum 'C16 H19 B F4 N2' _chemical_formula_weight 326.14 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/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 12.8809(6) _cell_length_b 8.8823(4) _cell_length_c 13.1761(6) _cell_angle_alpha 90.00 _cell_angle_beta 97.9550(10) _cell_angle_gamma 90.00 _cell_volume 1493.00(12) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 190 _cell_measurement_theta_min 3 _cell_measurement_theta_max 29 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.451 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 0.120 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.939 _exptl_absorpt_correction_T_max 0.982 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX II CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 14795 _diffrn_reflns_av_R_equivalents 0.0194 _diffrn_reflns_av_sigmaI/netI 0.0170 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.77 _diffrn_reflns_theta_max 29.00 _reflns_number_total 3948 _reflns_number_gt 3358 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX II' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement 'SHELXTL (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^+0.4369P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3948 _refine_ls_number_parameters 212 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0417 _refine_ls_R_factor_gt 0.0346 _refine_ls_wR_factor_ref 0.0975 _refine_ls_wR_factor_gt 0.0920 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _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 B1 B 0.39587(9) 0.31379(14) 0.13187(9) 0.0183(2) Uani 1 1 d . . . F1 F 0.43605(5) 0.25547(8) 0.04416(5) 0.02495(16) Uani 1 1 d . . . F2 F 0.46146(6) 0.26525(9) 0.21834(5) 0.03072(18) Uani 1 1 d . . . F3 F 0.29494(5) 0.25998(8) 0.13197(6) 0.02830(17) Uani 1 1 d . . . F4 F 0.39609(6) 0.46915(8) 0.12745(6) 0.03130(18) Uani 1 1 d . . . N1 N 0.85098(7) 0.08892(9) 0.01445(6) 0.01686(18) Uani 1 1 d . . . N2 N 0.64787(7) 0.20788(10) 0.04088(6) 0.01466(17) Uani 1 1 d . . . H2N H 0.5841(12) 0.2416(15) 0.0460(11) 0.021(3) Uiso 1 1 d . . . C1 C 0.89354(8) 0.22341(11) 0.06043(7) 0.01543(19) Uani 1 1 d . . . C2 C 1.00079(8) 0.24219(12) 0.07435(8) 0.0199(2) Uani 1 1 d . . . H2A H 1.0435 0.1638 0.0538 0.024 Uiso 1 1 calc R . . C3 C 1.04919(8) 0.37367(13) 0.11795(9) 0.0229(2) Uani 1 1 d . . . H3A H 1.1233 0.3838 0.1262 0.027 Uiso 1 1 calc R . . C4 C 0.98816(8) 0.48662(12) 0.14821(8) 0.0202(2) Uani 1 1 d . . . H4A H 1.0206 0.5751 0.1783 0.024 Uiso 1 1 calc R . . C5 C 0.87707(8) 0.47404(11) 0.13546(7) 0.01571(19) Uani 1 1 d . . . C6 C 0.81636(8) 0.59440(11) 0.16682(8) 0.0178(2) Uani 1 1 d . . . H6A H 0.8507 0.6808 0.1980 0.021 Uiso 1 1 calc R . . C7 C 0.70947(8) 0.58805(11) 0.15287(8) 0.0181(2) Uani 1 1 d . . . H7A H 0.6696 0.6704 0.1726 0.022 Uiso 1 1 calc R . . C8 C 0.65876(8) 0.45845(11) 0.10901(7) 0.01564(19) Uani 1 1 d . . . H8A H 0.5843 0.4545 0.0987 0.019 Uiso 1 1 calc R . . C9 C 0.71480(7) 0.33749(11) 0.08075(7) 0.01311(18) Uani 1 1 d . . . C10 C 0.82710(7) 0.34041(11) 0.09094(7) 0.01364(18) Uani 1 1 d . . . C11 C 0.81925(9) 0.08930(12) -0.09554(8) 0.0196(2) Uani 1 1 d . . . H11A H 0.7941 -0.0123 -0.1179 0.024 Uiso 1 1 calc R . . H11B H 0.8806 0.1132 -0.1303 0.024 Uiso 1 1 calc R . . C12 C 0.73286(9) 0.20365(12) -0.12725(8) 0.0195(2) Uani 1 1 d . . . H12A H 0.7604 0.3060 -0.1103 0.023 Uiso 1 1 calc R . . H12B H 0.7126 0.1985 -0.2024 0.023 Uiso 1 1 calc R . . C13 C 0.63647(8) 0.17840(12) -0.07547(7) 0.0194(2) Uani 1 1 d . . . H13A H 0.6135 0.0728 -0.0879 0.023 Uiso 1 1 calc R . . H13B H 0.5798 0.2438 -0.1093 0.023 Uiso 1 1 calc R . . C14 C 0.65257(8) 0.06874(11) 0.11106(8) 0.01727(19) Uani 1 1 d . . . H14A H 0.6114 0.0912 0.1673 0.021 Uiso 1 1 calc R . . H14B H 0.6170 -0.0153 0.0709 0.021 Uiso 1 1 calc R . . C15 C 0.75964(8) 0.01422(11) 0.15849(7) 0.01629(19) Uani 1 1 d . . . H15A H 0.7506 -0.0717 0.2043 0.020 Uiso 1 1 calc R . . H15B H 0.7950 0.0960 0.2011 0.020 Uiso 1 1 calc R . . C16 C 0.83000(8) -0.03473(11) 0.08049(8) 0.0177(2) Uani 1 1 d . . . H16A H 0.8971 -0.0733 0.1170 0.021 Uiso 1 1 calc R . . H16B H 0.7957 -0.1176 0.0382 0.021 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 B1 0.0160(5) 0.0203(5) 0.0188(5) 0.0024(4) 0.0029(4) 0.0006(4) F1 0.0188(3) 0.0318(4) 0.0247(3) -0.0059(3) 0.0046(2) 0.0030(3) F2 0.0238(3) 0.0429(4) 0.0241(4) 0.0108(3) -0.0017(3) 0.0013(3) F3 0.0166(3) 0.0369(4) 0.0320(4) 0.0009(3) 0.0055(3) -0.0030(3) F4 0.0377(4) 0.0198(3) 0.0369(4) 0.0000(3) 0.0068(3) 0.0027(3) N1 0.0233(4) 0.0140(4) 0.0135(4) -0.0002(3) 0.0037(3) 0.0016(3) N2 0.0143(4) 0.0142(4) 0.0152(4) -0.0006(3) 0.0009(3) 0.0009(3) C1 0.0177(4) 0.0157(4) 0.0132(4) 0.0010(3) 0.0034(3) 0.0023(3) C2 0.0170(5) 0.0229(5) 0.0203(5) 0.0014(4) 0.0046(4) 0.0042(4) C3 0.0147(5) 0.0290(6) 0.0243(5) 0.0028(4) 0.0008(4) -0.0002(4) C4 0.0185(5) 0.0208(5) 0.0202(5) 0.0011(4) -0.0013(4) -0.0035(4) C5 0.0181(4) 0.0154(4) 0.0133(4) 0.0014(3) 0.0006(3) -0.0002(4) C6 0.0246(5) 0.0130(4) 0.0154(4) -0.0004(3) 0.0011(4) -0.0004(4) C7 0.0240(5) 0.0139(4) 0.0167(4) -0.0001(3) 0.0038(4) 0.0042(4) C8 0.0163(4) 0.0154(4) 0.0154(4) 0.0015(3) 0.0029(3) 0.0029(3) C9 0.0155(4) 0.0125(4) 0.0111(4) 0.0004(3) 0.0011(3) 0.0006(3) C10 0.0156(4) 0.0144(4) 0.0110(4) 0.0011(3) 0.0019(3) 0.0015(3) C11 0.0273(5) 0.0188(5) 0.0137(4) -0.0025(4) 0.0056(4) 0.0024(4) C12 0.0279(5) 0.0180(5) 0.0124(4) -0.0003(4) 0.0017(4) 0.0007(4) C13 0.0228(5) 0.0199(5) 0.0140(5) -0.0025(4) -0.0026(4) -0.0001(4) C14 0.0181(5) 0.0151(4) 0.0190(5) 0.0026(3) 0.0041(4) -0.0003(4) C15 0.0199(5) 0.0144(4) 0.0149(4) 0.0018(3) 0.0038(3) 0.0026(3) C16 0.0217(5) 0.0139(4) 0.0182(5) 0.0012(4) 0.0052(4) 0.0043(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag B1 F4 1.3812(14) . ? B1 F3 1.3853(13) . ? B1 F2 1.3897(13) . ? B1 F1 1.4273(13) . ? N1 C1 1.4152(13) . ? N1 C16 1.4496(13) . ? N1 C11 1.4504(13) . ? N2 C9 1.4897(12) . ? N2 C14 1.5397(13) . ? N2 C13 1.5421(13) . ? N2 H2N 0.886(15) . ? C1 C2 1.3784(14) . ? C1 C10 1.4384(13) . ? C2 C3 1.4083(16) . ? C2 H2A 0.9500 . ? C3 C4 1.3676(16) . ? C3 H3A 0.9500 . ? C4 C5 1.4219(14) . ? C4 H4A 0.9500 . ? C5 C6 1.4194(14) . ? C5 C10 1.4362(13) . ? C6 C7 1.3648(15) . ? C6 H6A 0.9500 . ? C7 C8 1.4076(14) . ? C7 H7A 0.9500 . ? C8 C9 1.3742(13) . ? C8 H8A 0.9500 . ? C9 C10 1.4344(13) . ? C11 C12 1.5217(15) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.5139(15) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.5128(14) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.5246(13) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? 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 F4 B1 F3 110.61(9) . . ? F4 B1 F2 109.87(10) . . ? F3 B1 F2 110.87(9) . . ? F4 B1 F1 108.99(9) . . ? F3 B1 F1 108.73(9) . . ? F2 B1 F1 107.69(9) . . ? C1 N1 C16 118.42(8) . . ? C1 N1 C11 117.69(8) . . ? C16 N1 C11 123.46(9) . . ? C9 N2 C14 115.83(7) . . ? C9 N2 C13 116.91(8) . . ? C14 N2 C13 116.82(8) . . ? C9 N2 H2N 102.1(9) . . ? C14 N2 H2N 100.7(9) . . ? C13 N2 H2N 99.8(9) . . ? C2 C1 N1 118.74(9) . . ? C2 C1 C10 119.97(9) . . ? N1 C1 C10 121.29(9) . . ? C1 C2 C3 122.24(10) . . ? C1 C2 H2A 118.9 . . ? C3 C2 H2A 118.9 . . ? C4 C3 C2 119.17(10) . . ? C4 C3 H3A 120.4 . . ? C2 C3 H3A 120.4 . . ? C3 C4 C5 121.17(10) . . ? C3 C4 H4A 119.4 . . ? C5 C4 H4A 119.4 . . ? C6 C5 C4 119.50(9) . . ? C6 C5 C10 120.50(9) . . ? C4 C5 C10 120.00(9) . . ? C7 C6 C5 121.05(9) . . ? C7 C6 H6A 119.5 . . ? C5 C6 H6A 119.5 . . ? C6 C7 C8 119.42(9) . . ? C6 C7 H7A 120.3 . . ? C8 C7 H7A 120.3 . . ? C9 C8 C7 121.29(9) . . ? C9 C8 H8A 119.4 . . ? C7 C8 H8A 119.4 . . ? C8 C9 C10 121.41(9) . . ? C8 C9 N2 113.56(8) . . ? C10 C9 N2 125.02(8) . . ? C9 C10 C5 116.25(8) . . ? C9 C10 C1 126.30(9) . . ? C5 C10 C1 117.44(9) . . ? N1 C11 C12 111.72(8) . . ? N1 C11 H11A 109.3 . . ? C12 C11 H11A 109.3 . . ? N1 C11 H11B 109.3 . . ? C12 C11 H11B 109.3 . . ? H11A C11 H11B 107.9 . . ? C13 C12 C11 113.05(9) . . ? C13 C12 H12A 109.0 . . ? C11 C12 H12A 109.0 . . ? C13 C12 H12B 109.0 . . ? C11 C12 H12B 109.0 . . ? H12A C12 H12B 107.8 . . ? C12 C13 N2 116.85(8) . . ? C12 C13 H13A 108.1 . . ? N2 C13 H13A 108.1 . . ? C12 C13 H13B 108.1 . . ? N2 C13 H13B 108.1 . . ? H13A C13 H13B 107.3 . . ? C15 C14 N2 117.58(8) . . ? C15 C14 H14A 107.9 . . ? N2 C14 H14A 107.9 . . ? C15 C14 H14B 107.9 . . ? N2 C14 H14B 107.9 . . ? H14A C14 H14B 107.2 . . ? C14 C15 C16 113.94(8) . . ? C14 C15 H15A 108.8 . . ? C16 C15 H15A 108.8 . . ? C14 C15 H15B 108.8 . . ? C16 C15 H15B 108.8 . . ? H15A C15 H15B 107.7 . . ? N1 C16 C15 111.48(8) . . ? N1 C16 H16A 109.3 . . ? C15 C16 H16A 109.3 . . ? N1 C16 H16B 109.3 . . ? C15 C16 H16B 109.3 . . ? H16A C16 H16B 108.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 N1 C1 C2 93.69(11) . . . . ? C11 N1 C1 C2 -93.53(11) . . . . ? C16 N1 C1 C10 -87.33(11) . . . . ? C11 N1 C1 C10 85.45(11) . . . . ? N1 C1 C2 C3 178.94(9) . . . . ? C10 C1 C2 C3 -0.06(15) . . . . ? C1 C2 C3 C4 0.39(16) . . . . ? C2 C3 C4 C5 -0.63(16) . . . . ? C3 C4 C5 C6 -179.32(10) . . . . ? C3 C4 C5 C10 0.54(15) . . . . ? C4 C5 C6 C7 177.98(9) . . . . ? C10 C5 C6 C7 -1.88(15) . . . . ? C5 C6 C7 C8 1.61(15) . . . . ? C6 C7 C8 C9 0.58(15) . . . . ? C7 C8 C9 C10 -2.51(15) . . . . ? C7 C8 C9 N2 176.97(8) . . . . ? C14 N2 C9 C8 -109.04(9) . . . . ? C13 N2 C9 C8 107.07(10) . . . . ? C14 N2 C9 C10 70.41(11) . . . . ? C13 N2 C9 C10 -73.48(12) . . . . ? C8 C9 C10 C5 2.14(13) . . . . ? N2 C9 C10 C5 -177.27(8) . . . . ? C8 C9 C10 C1 -177.47(9) . . . . ? N2 C9 C10 C1 3.12(15) . . . . ? C6 C5 C10 C9 0.01(13) . . . . ? C4 C5 C10 C9 -179.85(9) . . . . ? C6 C5 C10 C1 179.66(9) . . . . ? C4 C5 C10 C1 -0.21(13) . . . . ? C2 C1 C10 C9 179.58(9) . . . . ? N1 C1 C10 C9 0.61(15) . . . . ? C2 C1 C10 C5 -0.03(14) . . . . ? N1 C1 C10 C5 -179.00(8) . . . . ? C1 N1 C11 C12 -61.48(12) . . . . ? C16 N1 C11 C12 110.90(11) . . . . ? N1 C11 C12 C13 -57.42(12) . . . . ? C11 C12 C13 N2 68.43(12) . . . . ? C9 N2 C13 C12 37.55(12) . . . . ? C14 N2 C13 C12 -105.98(10) . . . . ? C9 N2 C14 C15 -46.41(12) . . . . ? C13 N2 C14 C15 97.51(10) . . . . ? N2 C14 C15 C16 -61.54(12) . . . . ? C1 N1 C16 C15 54.74(12) . . . . ? C11 N1 C16 C15 -117.58(10) . . . . ? C14 C15 C16 N1 61.64(11) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag N2 H2N F1 1_555 0.89(2) 1.91(2) 2.767(1) 163(1) ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 29.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.357 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.044 _database_code_depnum_ccdc_archive 'CCDC 956638'