# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_1 _database_code_depnum_ccdc_archive 'CCDC 875185' #TrackingRef '1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C62 H72 N14 O5' _chemical_formula_sum 'C62 H72 N14 O5' _chemical_formula_weight 1093.34 _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 Pbcn _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y, -z+1/2' '-x+1/2, -y+1/2, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y, z-1/2' 'x-1/2, y-1/2, -z-1/2' _cell_length_a 18.9880(12) _cell_length_b 18.1378(11) _cell_length_c 16.5208(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5689.8(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6792 _cell_measurement_theta_min 2.47 _cell_measurement_theta_max 27.22 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.55 _exptl_crystal_size_min 0.50 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.276 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2328 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9513 _exptl_absorpt_correction_T_max 0.9592 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 27220 _diffrn_reflns_av_R_equivalents 0.0347 _diffrn_reflns_av_sigmaI/netI 0.0246 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 25.25 _reflns_number_total 5155 _reflns_number_gt 4182 _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^)+(0.0458P)^2^+2.3483P] 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 5155 _refine_ls_number_parameters 372 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0498 _refine_ls_R_factor_gt 0.0379 _refine_ls_wR_factor_ref 0.1023 _refine_ls_wR_factor_gt 0.0940 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.027 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _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 0.81169(8) 0.14650(8) 0.41879(9) 0.0240(3) Uani 1 1 d . . . C2 C 0.79981(9) 0.18122(8) 0.33776(9) 0.0286(4) Uani 1 1 d . . . H2A H 0.8296 0.2258 0.3327 0.034 Uiso 1 1 calc R . . H2B H 0.7500 0.1966 0.3331 0.034 Uiso 1 1 calc R . . C3 C 0.81768(8) 0.12696(8) 0.26864(9) 0.0277(4) Uani 1 1 d . . . C4 C 0.76080(9) 0.06752(9) 0.26238(10) 0.0324(4) Uani 1 1 d . . . H4A H 0.7154 0.0906 0.2498 0.049 Uiso 1 1 calc R . . H4B H 0.7573 0.0411 0.3140 0.049 Uiso 1 1 calc R . . H4C H 0.7732 0.0327 0.2193 0.049 Uiso 1 1 calc R . . C5 C 0.82208(10) 0.16992(9) 0.18886(9) 0.0349(4) Uani 1 1 d . . . H5A H 0.8316 0.1357 0.1443 0.052 Uiso 1 1 calc R . . H5B H 0.8601 0.2063 0.1923 0.052 Uiso 1 1 calc R . . H5C H 0.7773 0.1952 0.1790 0.052 Uiso 1 1 calc R . . C6 C 0.89003(9) 0.09123(9) 0.28517(9) 0.0300(4) Uani 1 1 d . . . H6A H 0.8997 0.0550 0.2418 0.036 Uiso 1 1 calc R . . H6B H 0.9266 0.1300 0.2817 0.036 Uiso 1 1 calc R . . C7 C 0.89708(8) 0.05273(9) 0.36613(9) 0.0277(3) Uani 1 1 d . . . C8 C 0.85847(8) 0.08735(8) 0.43114(9) 0.0237(3) Uani 1 1 d . . . C9 C 0.85659(8) 0.07255(8) 0.51380(9) 0.0233(3) Uani 1 1 d . . . C10 C 0.89413(9) 0.01504(9) 0.56143(9) 0.0308(4) Uani 1 1 d . . . H10A H 0.9381 0.0355 0.5828 0.046 Uiso 1 1 calc R . . H10B H 0.9047 -0.0271 0.5264 0.046 Uiso 1 1 calc R . . H10C H 0.8643 -0.0011 0.6065 0.046 Uiso 1 1 calc R . . C11 C 0.78716(8) 0.12728(8) 0.62723(9) 0.0229(3) Uani 1 1 d . . . C12 C 0.71574(8) 0.13171(8) 0.64196(9) 0.0222(3) Uani 1 1 d . . . H12 H 0.6840 0.1327 0.5975 0.027 Uiso 1 1 calc R . . C13 C 0.68902(7) 0.13482(8) 0.72055(9) 0.0213(3) Uani 1 1 d . . . C14 C 0.61165(8) 0.14428(8) 0.73271(9) 0.0220(3) Uani 1 1 d . . . C15 C 0.73680(7) 0.13127(8) 0.78734(9) 0.0217(3) Uani 1 1 d . . . C16 C 0.80957(8) 0.13027(8) 0.76957(9) 0.0244(3) Uani 1 1 d . . . H16 H 0.8424 0.1309 0.8130 0.029 Uiso 1 1 calc R . . C17 C 0.83445(8) 0.12837(8) 0.69156(9) 0.0251(3) Uani 1 1 d . . . H17 H 0.8837 0.1278 0.6816 0.030 Uiso 1 1 calc R . . C18 C 0.75655(8) 0.12164(9) 0.93706(9) 0.0295(4) Uani 1 1 d . . . H18A H 0.7670 0.1714 0.9585 0.035 Uiso 1 1 calc R . . H18B H 0.8017 0.0971 0.9240 0.035 Uiso 1 1 calc R . . C19 C 0.71654(8) 0.07698(10) 0.99989(9) 0.0310(4) Uani 1 1 d . . . H19A H 0.7137 0.0250 0.9820 0.037 Uiso 1 1 calc R . . H19B H 0.7425 0.0783 1.0518 0.037 Uiso 1 1 calc R . . C20 C 0.59665(9) 0.04777(10) 1.03907(10) 0.0338(4) Uani 1 1 d . . . H20A H 0.5501 0.0698 1.0512 0.041 Uiso 1 1 calc R . . H20B H 0.6148 0.0250 1.0894 0.041 Uiso 1 1 calc R . . C21 C 0.58841(8) -0.01069(9) 0.97497(10) 0.0303(4) Uani 1 1 d . . . C22 C 0.57246(9) 0.00874(10) 0.89545(11) 0.0371(4) Uani 1 1 d . . . H22 H 0.5630 0.0587 0.8821 0.045 Uiso 1 1 calc R . . C23 C 0.57050(9) -0.04473(12) 0.83634(11) 0.0433(5) Uani 1 1 d . . . H23 H 0.5607 -0.0321 0.7817 0.052 Uiso 1 1 calc R . . C24 C 0.58308(10) -0.11720(12) 0.85805(11) 0.0455(5) Uani 1 1 d . . . H24 H 0.5824 -0.1555 0.8188 0.055 Uiso 1 1 calc R . . C25 C 0.59661(10) -0.13223(10) 0.93825(11) 0.0417(4) Uani 1 1 d . . . H25 H 0.6045 -0.1821 0.9532 0.050 Uiso 1 1 calc R . . C26 C 0.64407(9) 0.16821(10) 1.06836(10) 0.0367(4) Uani 1 1 d . . . H26A H 0.6867 0.1985 1.0593 0.044 Uiso 1 1 calc R . . H26B H 0.6460 0.1493 1.1245 0.044 Uiso 1 1 calc R . . C27 C 0.57980(9) 0.21671(10) 1.05951(11) 0.0394(4) Uani 1 1 d . . . C28 C 0.55533(10) 0.23810(10) 0.98419(13) 0.0444(5) Uani 1 1 d . . . H28 H 0.5756 0.2183 0.9363 0.053 Uiso 1 1 calc R . . C29 C 0.50087(11) 0.28886(11) 0.97955(17) 0.0609(6) Uani 1 1 d . . . H29 H 0.4835 0.3047 0.9285 0.073 Uiso 1 1 calc R . . C30 C 0.47236(12) 0.31590(12) 1.0501(2) 0.0684(7) Uani 1 1 d . . . H30 H 0.4359 0.3518 1.0490 0.082 Uiso 1 1 calc R . . C31 C 0.49787(12) 0.28976(14) 1.12177(19) 0.0723(8) Uani 1 1 d . . . H31 H 0.4767 0.3073 1.1702 0.087 Uiso 1 1 calc R . . N1 N 0.78183(7) 0.16804(7) 0.48713(7) 0.0255(3) Uani 1 1 d . . . N2 N 0.81119(6) 0.12197(7) 0.54526(7) 0.0228(3) Uani 1 1 d . . . N3 N 0.56868(7) 0.13455(8) 0.66949(8) 0.0309(3) Uani 1 1 d . . . H3A H 0.5230 0.1412 0.6751 0.037 Uiso 1 1 calc R . . H3B H 0.5860 0.1215 0.6222 0.037 Uiso 1 1 calc R . . N4 N 0.71358(6) 0.12744(7) 0.86488(7) 0.0267(3) Uani 1 1 d . . . H4 H 0.6677 0.1286 0.8721 0.032 Uiso 1 1 calc R . . N5 N 0.64516(7) 0.10568(7) 1.01232(8) 0.0288(3) Uani 1 1 d . . . N6 N 0.59931(7) -0.08071(8) 0.99679(8) 0.0338(3) Uani 1 1 d . . . N7 N 0.55125(9) 0.24064(10) 1.12896(11) 0.0576(5) Uani 1 1 d . . . O1 O 0.93378(6) -0.00265(7) 0.37469(7) 0.0410(3) Uani 1 1 d . . . O2 O 0.58674(5) 0.16285(6) 0.79963(6) 0.0274(3) Uani 1 1 d . . . O3 O 0.0000 0.07896(10) 0.7500 0.0385(4) Uani 1 2 d SD . . H3 H 0.0194(11) 0.0480(10) 0.7121(11) 0.058 Uiso 1 1 d D . . _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 0.0238(8) 0.0253(8) 0.0228(8) -0.0011(6) -0.0011(6) -0.0014(6) C2 0.0348(9) 0.0248(8) 0.0260(8) 0.0011(6) -0.0017(7) 0.0017(7) C3 0.0327(9) 0.0274(8) 0.0230(8) 0.0005(6) -0.0033(6) 0.0005(7) C4 0.0361(9) 0.0311(9) 0.0300(9) 0.0004(7) -0.0054(7) -0.0009(7) C5 0.0504(11) 0.0304(9) 0.0239(8) 0.0010(7) -0.0039(7) -0.0002(8) C6 0.0316(9) 0.0369(9) 0.0216(8) -0.0014(7) 0.0027(7) 0.0019(7) C7 0.0241(8) 0.0351(9) 0.0238(8) -0.0027(7) -0.0015(6) 0.0022(7) C8 0.0229(7) 0.0265(8) 0.0217(8) -0.0006(6) 0.0002(6) -0.0004(6) C9 0.0195(7) 0.0266(8) 0.0239(8) -0.0013(6) -0.0002(6) 0.0001(6) C10 0.0334(9) 0.0343(9) 0.0248(8) 0.0006(7) -0.0009(7) 0.0086(7) C11 0.0233(8) 0.0239(8) 0.0216(8) -0.0022(6) 0.0026(6) -0.0004(6) C12 0.0220(7) 0.0235(8) 0.0212(7) -0.0008(6) -0.0026(6) 0.0005(6) C13 0.0199(7) 0.0205(7) 0.0235(8) -0.0010(6) 0.0001(6) -0.0002(6) C14 0.0210(7) 0.0219(7) 0.0230(8) 0.0021(6) 0.0002(6) -0.0004(6) C15 0.0217(7) 0.0209(7) 0.0226(7) -0.0017(6) 0.0003(6) 0.0006(6) C16 0.0201(7) 0.0304(8) 0.0228(8) -0.0009(6) -0.0036(6) -0.0005(6) C17 0.0187(7) 0.0300(8) 0.0266(8) -0.0017(6) 0.0019(6) -0.0016(6) C18 0.0231(8) 0.0418(9) 0.0234(8) -0.0003(7) -0.0022(6) -0.0011(7) C19 0.0255(8) 0.0417(10) 0.0258(8) 0.0030(7) -0.0039(7) 0.0012(7) C20 0.0289(9) 0.0406(10) 0.0320(9) 0.0046(7) 0.0042(7) -0.0028(7) C21 0.0206(8) 0.0366(9) 0.0337(9) 0.0073(7) 0.0014(6) -0.0032(7) C22 0.0291(9) 0.0450(10) 0.0372(10) 0.0121(8) -0.0048(7) -0.0062(8) C23 0.0330(10) 0.0655(13) 0.0315(10) 0.0055(9) -0.0045(8) -0.0140(9) C24 0.0390(10) 0.0566(12) 0.0409(11) -0.0085(9) 0.0037(8) -0.0120(9) C25 0.0387(10) 0.0377(10) 0.0486(11) 0.0004(8) -0.0004(8) -0.0039(8) C26 0.0335(9) 0.0448(10) 0.0318(9) -0.0051(8) 0.0005(7) -0.0066(8) C27 0.0303(9) 0.0385(10) 0.0494(11) -0.0134(8) 0.0093(8) -0.0089(8) C28 0.0361(10) 0.0393(10) 0.0578(13) 0.0017(9) 0.0115(9) 0.0024(8) C29 0.0412(11) 0.0439(12) 0.0976(18) 0.0105(12) 0.0112(12) 0.0006(10) C30 0.0419(12) 0.0406(12) 0.123(2) -0.0208(14) 0.0170(15) 0.0026(10) C31 0.0392(12) 0.0697(16) 0.108(2) -0.0590(16) 0.0173(13) -0.0090(12) N1 0.0261(7) 0.0266(7) 0.0238(7) 0.0011(5) -0.0010(5) 0.0028(5) N2 0.0206(6) 0.0283(7) 0.0196(6) 0.0005(5) 0.0007(5) 0.0018(5) N3 0.0181(6) 0.0486(9) 0.0259(7) -0.0098(6) 0.0002(5) 0.0018(6) N4 0.0171(6) 0.0412(8) 0.0217(7) 0.0026(6) -0.0003(5) 0.0018(6) N5 0.0233(7) 0.0338(7) 0.0294(7) 0.0010(6) 0.0024(5) -0.0015(6) N6 0.0279(7) 0.0366(8) 0.0370(8) 0.0078(6) -0.0016(6) -0.0034(6) N7 0.0378(9) 0.0690(12) 0.0661(12) -0.0401(10) 0.0113(8) -0.0122(9) O1 0.0432(7) 0.0521(8) 0.0276(6) -0.0005(5) 0.0029(5) 0.0235(6) O2 0.0202(5) 0.0400(7) 0.0222(6) 0.0001(5) 0.0026(4) 0.0033(5) O3 0.0445(10) 0.0354(10) 0.0355(10) 0.000 0.0100(8) 0.000 _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. ; _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 1.3225(19) . ? C1 C8 1.408(2) . ? C1 C2 1.496(2) . ? C2 C3 1.545(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.529(2) . ? C3 C5 1.533(2) . ? C3 C6 1.543(2) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 C7 1.515(2) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 O1 1.2308(19) . ? C7 C8 1.444(2) . ? C8 C9 1.392(2) . ? C9 N2 1.3478(19) . ? C9 C10 1.488(2) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.380(2) . ? C11 C17 1.391(2) . ? C11 N2 1.4323(18) . ? C12 C13 1.395(2) . ? C12 H12 0.9500 . ? C13 C15 1.430(2) . ? C13 C14 1.493(2) . ? C14 O2 1.2488(17) . ? C14 N3 1.3370(19) . ? C15 N4 1.3567(18) . ? C15 C16 1.413(2) . ? C16 C17 1.373(2) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 N4 1.4487(19) . ? C18 C19 1.520(2) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 N5 1.466(2) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 N5 1.465(2) . ? C20 C21 1.507(2) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 N6 1.336(2) . ? C21 C22 1.393(2) . ? C22 C23 1.377(3) . ? C22 H22 0.9500 . ? C23 C24 1.383(3) . ? C23 H23 0.9500 . ? C24 C25 1.377(3) . ? C24 H24 0.9500 . ? C25 N6 1.346(2) . ? C25 H25 0.9500 . ? C26 N5 1.464(2) . ? C26 C27 1.511(3) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 N7 1.341(2) . ? C27 C28 1.384(3) . ? C28 C29 1.387(3) . ? C28 H28 0.9500 . ? C29 C30 1.376(3) . ? C29 H29 0.9500 . ? C30 C31 1.364(4) . ? C30 H30 0.9500 . ? C31 N7 1.355(3) . ? C31 H31 0.9500 . ? N1 N2 1.3898(17) . ? N3 H3A 0.8800 . ? N3 H3B 0.8800 . ? N4 H4 0.8800 . ? O3 H3 0.918(14) . ? _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 C8 111.83(13) . . ? N1 C1 C2 125.08(13) . . ? C8 C1 C2 123.06(13) . . ? C1 C2 C3 111.09(12) . . ? C1 C2 H2A 109.4 . . ? C3 C2 H2A 109.4 . . ? C1 C2 H2B 109.4 . . ? C3 C2 H2B 109.4 . . ? H2A C2 H2B 108.0 . . ? C4 C3 C5 109.79(13) . . ? C4 C3 C6 110.16(13) . . ? C5 C3 C6 108.48(13) . . ? C4 C3 C2 110.11(13) . . ? C5 C3 C2 108.87(13) . . ? C6 C3 C2 109.40(12) . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C3 C5 H5A 109.5 . . ? C3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C7 C6 C3 115.37(13) . . ? C7 C6 H6A 108.4 . . ? C3 C6 H6A 108.4 . . ? C7 C6 H6B 108.4 . . ? C3 C6 H6B 108.4 . . ? H6A C6 H6B 107.5 . . ? O1 C7 C8 123.85(14) . . ? O1 C7 C6 121.85(14) . . ? C8 C7 C6 114.29(13) . . ? C9 C8 C1 105.85(13) . . ? C9 C8 C7 131.19(14) . . ? C1 C8 C7 122.95(13) . . ? N2 C9 C8 105.44(13) . . ? N2 C9 C10 124.65(13) . . ? C8 C9 C10 129.91(14) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 C17 119.91(13) . . ? C12 C11 N2 118.92(13) . . ? C17 C11 N2 121.17(13) . . ? C11 C12 C13 121.59(13) . . ? C11 C12 H12 119.2 . . ? C13 C12 H12 119.2 . . ? C12 C13 C15 119.05(13) . . ? C12 C13 C14 119.20(13) . . ? C15 C13 C14 121.72(13) . . ? O2 C14 N3 119.74(13) . . ? O2 C14 C13 121.53(13) . . ? N3 C14 C13 118.70(13) . . ? N4 C15 C16 120.89(13) . . ? N4 C15 C13 121.66(13) . . ? C16 C15 C13 117.44(13) . . ? C17 C16 C15 122.13(14) . . ? C17 C16 H16 118.9 . . ? C15 C16 H16 118.9 . . ? C16 C17 C11 119.69(14) . . ? C16 C17 H17 120.2 . . ? C11 C17 H17 120.2 . . ? N4 C18 C19 108.62(13) . . ? N4 C18 H18A 110.0 . . ? C19 C18 H18A 110.0 . . ? N4 C18 H18B 110.0 . . ? C19 C18 H18B 110.0 . . ? H18A C18 H18B 108.3 . . ? N5 C19 C18 111.61(13) . . ? N5 C19 H19A 109.3 . . ? C18 C19 H19A 109.3 . . ? N5 C19 H19B 109.3 . . ? C18 C19 H19B 109.3 . . ? H19A C19 H19B 108.0 . . ? N5 C20 C21 110.96(13) . . ? N5 C20 H20A 109.4 . . ? C21 C20 H20A 109.4 . . ? N5 C20 H20B 109.4 . . ? C21 C20 H20B 109.4 . . ? H20A C20 H20B 108.0 . . ? N6 C21 C22 121.90(16) . . ? N6 C21 C20 117.59(14) . . ? C22 C21 C20 120.48(15) . . ? C23 C22 C21 119.77(17) . . ? C23 C22 H22 120.1 . . ? C21 C22 H22 120.1 . . ? C22 C23 C24 118.73(17) . . ? C22 C23 H23 120.6 . . ? C24 C23 H23 120.6 . . ? C25 C24 C23 118.03(18) . . ? C25 C24 H24 121.0 . . ? C23 C24 H24 121.0 . . ? N6 C25 C24 124.13(18) . . ? N6 C25 H25 117.9 . . ? C24 C25 H25 117.9 . . ? N5 C26 C27 113.64(14) . . ? N5 C26 H26A 108.8 . . ? C27 C26 H26A 108.8 . . ? N5 C26 H26B 108.8 . . ? C27 C26 H26B 108.8 . . ? H26A C26 H26B 107.7 . . ? N7 C27 C28 122.88(18) . . ? N7 C27 C26 115.59(18) . . ? C28 C27 C26 121.42(16) . . ? C27 C28 C29 119.1(2) . . ? C27 C28 H28 120.5 . . ? C29 C28 H28 120.5 . . ? C30 C29 C28 118.9(2) . . ? C30 C29 H29 120.5 . . ? C28 C29 H29 120.5 . . ? C31 C30 C29 118.1(2) . . ? C31 C30 H30 120.9 . . ? C29 C30 H30 120.9 . . ? N7 C31 C30 124.8(2) . . ? N7 C31 H31 117.6 . . ? C30 C31 H31 117.6 . . ? C1 N1 N2 103.90(12) . . ? C9 N2 N1 112.96(12) . . ? C9 N2 C11 127.81(12) . . ? N1 N2 C11 119.02(11) . . ? C14 N3 H3A 120.0 . . ? C14 N3 H3B 120.0 . . ? H3A N3 H3B 120.0 . . ? C15 N4 C18 126.73(12) . . ? C15 N4 H4 116.6 . . ? C18 N4 H4 116.6 . . ? C26 N5 C20 110.83(13) . . ? C26 N5 C19 112.12(13) . . ? C20 N5 C19 111.64(13) . . ? C21 N6 C25 117.39(15) . . ? C27 N7 C31 116.1(2) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.25 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.217 _refine_diff_density_min -0.173 _refine_diff_density_rms 0.036 data_1 _database_code_depnum_ccdc_archive 'CCDC 875205' #TrackingRef '1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H16 Br N3 O' _chemical_formula_sum 'C17 H16 Br N3 O' _chemical_formula_weight 358.24 _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' Br Br -0.2901 2.4595 '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_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 11.0531(7) _cell_length_b 14.3809(9) _cell_length_c 10.6995(7) _cell_angle_alpha 90.00 _cell_angle_beta 107.9540(10) _cell_angle_gamma 90.00 _cell_volume 1617.90(18) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2884 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 25.38 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.471 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 2.546 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.3626 _exptl_absorpt_correction_T_max 0.5802 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 9425 _diffrn_reflns_av_R_equivalents 0.0230 _diffrn_reflns_av_sigmaI/netI 0.0300 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.40 _diffrn_reflns_theta_max 27.60 _reflns_number_total 3682 _reflns_number_gt 2680 _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^)+(0.0347P)^2^+0.4602P] 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 3682 _refine_ls_number_parameters 202 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0550 _refine_ls_R_factor_gt 0.0330 _refine_ls_wR_factor_ref 0.0801 _refine_ls_wR_factor_gt 0.0731 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.007 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _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 0.34127(2) 0.039854(18) 0.91188(3) 0.06846(12) Uani 1 1 d . . . C1 C 0.1922(3) -0.01055(18) 0.6211(3) 0.0615(6) Uani 1 1 d . . . C2 C 0.2001(2) 0.08773(14) 0.6487(2) 0.0466(5) Uani 1 1 d . . . C3 C 0.26365(18) 0.12188(14) 0.7729(2) 0.0421(5) Uani 1 1 d . . . C4 C 0.26919(18) 0.21582(14) 0.7977(2) 0.0417(5) Uani 1 1 d . . . H4 H 0.3128 0.2384 0.8808 0.050 Uiso 1 1 calc R . . C5 C 0.20873(18) 0.27626(14) 0.6971(2) 0.0409(5) Uani 1 1 d . . . C6 C 0.1456(2) 0.24426(16) 0.5727(2) 0.0497(5) Uani 1 1 d . . . H6 H 0.1067 0.2857 0.5056 0.060 Uiso 1 1 calc R . . C7 C 0.1409(2) 0.14975(17) 0.5492(2) 0.0548(6) Uani 1 1 d . . . H7 H 0.0977 0.1274 0.4658 0.066 Uiso 1 1 calc R . . C8 C 0.12058(19) 0.43648(14) 0.6991(2) 0.0414(5) Uani 1 1 d . . . C9 C -0.0161(2) 0.41334(17) 0.6369(2) 0.0549(6) Uani 1 1 d . . . H9A H -0.0352 0.4133 0.5430 0.082 Uiso 1 1 calc R . . H9B H -0.0680 0.4588 0.6618 0.082 Uiso 1 1 calc R . . H9C H -0.0334 0.3529 0.6656 0.082 Uiso 1 1 calc R . . C10 C 0.17836(19) 0.51991(14) 0.7475(2) 0.0402(5) Uani 1 1 d . . . C11 C 0.1282(2) 0.61388(15) 0.74406(19) 0.0429(5) Uani 1 1 d . . . C12 C 0.2272(2) 0.68658(15) 0.8070(2) 0.0477(5) Uani 1 1 d . . . H12A H 0.2335 0.6913 0.8993 0.057 Uiso 1 1 calc R . . H12B H 0.1980 0.7462 0.7667 0.057 Uiso 1 1 calc R . . C13 C 0.3607(2) 0.66783(14) 0.7965(2) 0.0420(5) Uani 1 1 d . . . C14 C 0.4531(2) 0.74314(17) 0.8704(3) 0.0635(7) Uani 1 1 d . . . H14A H 0.5355 0.7322 0.8609 0.095 Uiso 1 1 calc R . . H14B H 0.4590 0.7414 0.9618 0.095 Uiso 1 1 calc R . . H14C H 0.4226 0.8030 0.8348 0.095 Uiso 1 1 calc R . . C15 C 0.3549(2) 0.66953(17) 0.6519(2) 0.0566(6) Uani 1 1 d . . . H15A H 0.4379 0.6573 0.6449 0.085 Uiso 1 1 calc R . . H15B H 0.3265 0.7296 0.6153 0.085 Uiso 1 1 calc R . . H15C H 0.2966 0.6228 0.6047 0.085 Uiso 1 1 calc R . . C16 C 0.4068(2) 0.57286(15) 0.8583(2) 0.0486(5) Uani 1 1 d . . . H16A H 0.4860 0.5568 0.8425 0.058 Uiso 1 1 calc R . . H16B H 0.4224 0.5760 0.9525 0.058 Uiso 1 1 calc R . . C17 C 0.30976(19) 0.50002(15) 0.8011(2) 0.0430(5) Uani 1 1 d . . . N1 N 0.1842(3) -0.08794(17) 0.5978(3) 0.0904(8) Uani 1 1 d . . . N2 N 0.21596(15) 0.37319(11) 0.72576(17) 0.0432(4) Uani 1 1 d . . . N3 N 0.33414(16) 0.41109(12) 0.78989(18) 0.0482(4) Uani 1 1 d . . . O1 O 0.01586(14) 0.63347(11) 0.69398(16) 0.0593(4) Uani 1 1 d . . . _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 0.05667(17) 0.05751(16) 0.0760(2) 0.02827(13) -0.00188(12) -0.00280(11) C1 0.0757(17) 0.0502(14) 0.0628(16) -0.0004(12) 0.0274(13) -0.0014(13) C2 0.0491(12) 0.0424(11) 0.0520(13) 0.0007(10) 0.0210(10) -0.0012(10) C3 0.0321(10) 0.0445(11) 0.0492(12) 0.0118(9) 0.0119(9) 0.0013(9) C4 0.0348(11) 0.0470(11) 0.0409(11) 0.0041(9) 0.0080(8) -0.0020(9) C5 0.0347(10) 0.0424(11) 0.0459(12) 0.0053(9) 0.0129(9) 0.0027(9) C6 0.0548(13) 0.0505(13) 0.0411(12) 0.0086(10) 0.0108(10) 0.0074(10) C7 0.0649(15) 0.0564(14) 0.0412(12) -0.0034(10) 0.0135(11) 0.0002(11) C8 0.0349(10) 0.0485(12) 0.0404(11) 0.0056(9) 0.0111(9) 0.0056(9) C9 0.0360(11) 0.0641(14) 0.0627(15) -0.0023(12) 0.0122(10) 0.0019(11) C10 0.0349(10) 0.0455(11) 0.0395(11) 0.0054(9) 0.0104(8) 0.0053(8) C11 0.0426(12) 0.0519(12) 0.0369(11) 0.0047(9) 0.0164(9) 0.0113(10) C12 0.0533(13) 0.0456(12) 0.0483(13) -0.0018(10) 0.0215(10) 0.0077(10) C13 0.0445(12) 0.0417(11) 0.0413(11) -0.0013(9) 0.0153(9) 0.0026(9) C14 0.0620(15) 0.0553(14) 0.0744(17) -0.0127(13) 0.0229(13) -0.0103(12) C15 0.0609(15) 0.0633(15) 0.0517(14) 0.0056(11) 0.0261(11) 0.0055(12) C16 0.0408(12) 0.0498(12) 0.0489(13) 0.0032(10) 0.0047(10) 0.0027(10) C17 0.0378(11) 0.0444(11) 0.0426(12) 0.0067(9) 0.0062(9) 0.0053(9) N1 0.129(2) 0.0528(14) 0.0936(19) -0.0079(13) 0.0400(17) -0.0031(14) N2 0.0363(9) 0.0395(9) 0.0495(10) 0.0027(8) 0.0068(8) 0.0024(7) N3 0.0352(9) 0.0435(10) 0.0587(11) 0.0045(8) 0.0041(8) 0.0038(8) O1 0.0429(9) 0.0638(10) 0.0673(11) 0.0042(8) 0.0114(8) 0.0188(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. ; _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C3 1.8850(19) . ? C1 N1 1.138(3) . ? C1 C2 1.441(3) . ? C2 C3 1.387(3) . ? C2 C7 1.388(3) . ? C3 C4 1.375(3) . ? C4 C5 1.385(3) . ? C4 H4 0.9300 . ? C5 C6 1.377(3) . ? C5 N2 1.424(3) . ? C6 C7 1.380(3) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 N2 1.355(2) . ? C8 C10 1.383(3) . ? C8 C9 1.489(3) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C17 1.416(3) . ? C10 C11 1.457(3) . ? C11 O1 1.224(2) . ? C11 C12 1.513(3) . ? C12 C13 1.539(3) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C15 1.529(3) . ? C13 C14 1.531(3) . ? C13 C16 1.534(3) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 C17 1.489(3) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 N3 1.320(3) . ? N2 N3 1.386(2) . ? _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 C2 178.9(3) . . ? C3 C2 C7 119.1(2) . . ? C3 C2 C1 121.6(2) . . ? C7 C2 C1 119.2(2) . . ? C4 C3 C2 120.83(18) . . ? C4 C3 Br1 118.69(16) . . ? C2 C3 Br1 120.47(15) . . ? C3 C4 C5 118.96(19) . . ? C3 C4 H4 120.5 . . ? C5 C4 H4 120.5 . . ? C6 C5 C4 121.39(19) . . ? C6 C5 N2 120.89(18) . . ? C4 C5 N2 117.71(18) . . ? C5 C6 C7 119.0(2) . . ? C5 C6 H6 120.5 . . ? C7 C6 H6 120.5 . . ? C6 C7 C2 120.7(2) . . ? C6 C7 H7 119.7 . . ? C2 C7 H7 119.7 . . ? N2 C8 C10 105.34(17) . . ? N2 C8 C9 124.08(19) . . ? C10 C8 C9 130.50(19) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 C17 105.90(18) . . ? C8 C10 C11 131.86(19) . . ? C17 C10 C11 122.15(19) . . ? O1 C11 C10 123.5(2) . . ? O1 C11 C12 122.17(19) . . ? C10 C11 C12 114.38(18) . . ? C11 C12 C13 115.10(17) . . ? C11 C12 H12A 108.5 . . ? C13 C12 H12A 108.5 . . ? C11 C12 H12B 108.5 . . ? C13 C12 H12B 108.5 . . ? H12A C12 H12B 107.5 . . ? C15 C13 C14 108.95(19) . . ? C15 C13 C16 110.80(18) . . ? C14 C13 C16 109.10(18) . . ? C15 C13 C12 109.25(18) . . ? C14 C13 C12 109.88(18) . . ? C16 C13 C12 108.83(17) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C16 C13 110.35(17) . . ? C17 C16 H16A 109.6 . . ? C13 C16 H16A 109.6 . . ? C17 C16 H16B 109.6 . . ? C13 C16 H16B 109.6 . . ? H16A C16 H16B 108.1 . . ? N3 C17 C10 111.81(18) . . ? N3 C17 C16 125.28(18) . . ? C10 C17 C16 122.88(19) . . ? C8 N2 N3 113.16(16) . . ? C8 N2 C5 128.60(17) . . ? N3 N2 C5 118.24(15) . . ? C17 N3 N2 103.79(15) . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 27.60 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.311 _refine_diff_density_min -0.476 _refine_diff_density_rms 0.052