# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2005 ####################################################################### # # 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_05jo0046_0m _database_code_depnum_ccdc_archive 'CCDC 285436' _audit_creation_date 2005-09-12T13:32:21-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C21 H17 N3 O2' _chemical_formula_sum 'C21 H17 N3 O2' _chemical_formula_weight 343.38 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 8.9902(5) _cell_length_b 23.0477(16) _cell_length_c 15.9796(11) _cell_angle_alpha 90 _cell_angle_beta 96.130(3) _cell_angle_gamma 90 _cell_volume 3292.1(4) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8534 _cell_measurement_theta_min 2.445 _cell_measurement_theta_max 26.143 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.03 _exptl_crystal_density_diffrn 1.386 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1440 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0806 _diffrn_reflns_av_unetI/netI 0.04 _diffrn_reflns_number 65363 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.54 _diffrn_reflns_theta_max 23.25 _diffrn_reflns_theta_full 23.25 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _reflns_number_total 4696 _reflns_number_gt 2974 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Apex2 (Bruker-Nonius, 2004)' _computing_cell_refinement 'Saint+ (Bruker-Nonius, 2004)' _computing_data_reduction 'Saint+ (Bruker-Nonius, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0662P)^2^+4.0000P] where P=(Fo^2^+2Fc^2^)/3 ; _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 4696 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1065 _refine_ls_R_factor_gt 0.0522 _refine_ls_wR_factor_ref 0.1476 _refine_ls_wR_factor_gt 0.1246 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.490 _refine_diff_density_min -0.339 _refine_diff_density_rms 0.069 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 N1B N 0.3891(3) 0.15493(12) 0.91795(18) 0.0268(7) Uani 1 1 d . . . N2B N 0.3933(3) 0.29836(14) 0.93174(17) 0.0226(7) Uani 1 1 d . . . H2C H 0.442(4) 0.2682(16) 0.949(2) 0.027 Uiso 1 1 d . . . H2D H 0.430(4) 0.3368(16) 0.941(2) 0.027 Uiso 1 1 d . . . N3B N 0.2055(3) 0.39766(11) 0.89044(15) 0.0181(6) Uani 1 1 d . . . O1B O 0.3221(2) 0.40721(9) 0.93910(13) 0.0233(5) Uani 1 1 d . . . O2B O 0.1263(2) 0.43865(9) 0.86051(13) 0.0231(5) Uani 1 1 d . . . C1B C 0.0509(3) 0.22507(13) 0.84476(18) 0.0145(7) Uiso 1 1 d . . . C2B C -0.0585(3) 0.27395(12) 0.82977(18) 0.0147(7) Uiso 1 1 d . . . H2B H -0.1234 0.2650 0.7766 0.018 Uiso 1 1 calc R . . C3B C 0.0103(3) 0.33433(13) 0.81865(18) 0.0152(7) Uiso 1 1 d . . . H3B H -0.0583 0.3634 0.8408 0.018 Uiso 1 1 calc R . . C4B C 0.1601(3) 0.34069(13) 0.86967(18) 0.0160(7) Uiso 1 1 d . . . C5B C -0.1582(3) 0.26935(13) 0.90254(19) 0.0171(7) Uiso 1 1 d . . . H5C H -0.0949 0.2699 0.9572 0.021 Uiso 1 1 calc R . . H5D H -0.2271 0.3029 0.9009 0.021 Uiso 1 1 calc R . . C6B C -0.2484(4) 0.21282(13) 0.89389(19) 0.0189(7) Uiso 1 1 d . . . H6C H -0.2841 0.2036 0.9489 0.023 Uiso 1 1 calc R . . H6D H -0.3376 0.2190 0.8529 0.023 Uiso 1 1 calc R . . C7B C -0.1625(3) 0.16123(13) 0.86574(18) 0.0152(7) Uiso 1 1 d . . . C8B C -0.2256(4) 0.10587(13) 0.86543(18) 0.0183(7) Uiso 1 1 d . . . H8B H -0.3217 0.1011 0.8841 0.022 Uiso 1 1 calc R . . C9B C -0.1516(4) 0.05777(14) 0.83855(19) 0.0222(8) Uiso 1 1 d . . . H9B H -0.1960 0.0204 0.8400 0.027 Uiso 1 1 calc R . . C10B C -0.0128(4) 0.06419(14) 0.80952(19) 0.0212(7) Uiso 1 1 d . . . H10B H 0.0366 0.0314 0.7894 0.025 Uiso 1 1 calc R . . C11B C 0.0536(4) 0.11817(13) 0.80982(18) 0.0179(7) Uiso 1 1 d . . . H11B H 0.1493 0.1223 0.7904 0.022 Uiso 1 1 calc R . . C12B C -0.0192(3) 0.16709(13) 0.83871(18) 0.0154(7) Uiso 1 1 d . . . C13B C 0.1960(3) 0.23546(13) 0.87312(18) 0.0170(7) Uiso 1 1 d . . . C14B C 0.0197(3) 0.34907(13) 0.72579(18) 0.0153(7) Uiso 1 1 d . . . C15B C 0.0960(4) 0.31341(14) 0.67516(19) 0.0217(8) Uiso 1 1 d . . . H15B H 0.1417 0.2790 0.6981 0.026 Uiso 1 1 calc R . . C16B C 0.1068(4) 0.32710(14) 0.5916(2) 0.0258(8) Uiso 1 1 d . . . H16B H 0.1586 0.3019 0.5577 0.031 Uiso 1 1 calc R . . C17B C 0.0423(4) 0.37721(14) 0.5576(2) 0.0226(8) Uiso 1 1 d . . . H17B H 0.0519 0.3873 0.5007 0.027 Uiso 1 1 calc R . . C18B C -0.0363(4) 0.41272(15) 0.6070(2) 0.0286(8) Uiso 1 1 d . . . H18B H -0.0830 0.4469 0.5836 0.034 Uiso 1 1 calc R . . C19B C -0.0476(4) 0.39870(14) 0.6906(2) 0.0249(8) Uiso 1 1 d . . . H19B H -0.1020 0.4234 0.7240 0.030 Uiso 1 1 calc R . . C20B C 0.2993(4) 0.18915(13) 0.89716(19) 0.0183(7) Uiso 1 1 d . . . C21B C 0.2536(3) 0.29462(13) 0.89189(18) 0.0160(7) Uiso 1 1 d . . . O1A O 0.1510(2) -0.07048(9) 0.56358(12) 0.0193(5) Uani 1 1 d . . . O2A O 0.3669(2) -0.10261(9) 0.62121(13) 0.0204(5) Uani 1 1 d . . . N1A N 0.0953(3) 0.18036(11) 0.58304(17) 0.0237(7) Uani 1 1 d . . . N2A N 0.0836(3) 0.03768(13) 0.57984(16) 0.0179(6) Uani 1 1 d . . . H2E H 0.033(4) 0.0687(15) 0.572(2) 0.022 Uiso 1 1 d . . . H2F H 0.041(4) 0.0003(15) 0.5724(19) 0.022 Uiso 1 1 d . . . N3A N 0.2787(3) -0.06156(11) 0.60255(15) 0.0156(6) Uani 1 1 d . . . C1A C 0.4360(3) 0.11019(12) 0.65261(17) 0.0132(7) Uiso 1 1 d . . . C2A C 0.5460(3) 0.06131(12) 0.66461(18) 0.0142(7) Uiso 1 1 d . . . H2A H 0.6113 0.0688 0.7182 0.017 Uiso 1 1 calc R . . C3A C 0.4790(3) 0.00003(13) 0.67123(17) 0.0134(7) Uiso 1 1 d . . . H3A H 0.5458 -0.0278 0.6452 0.016 Uiso 1 1 calc R . . C4A C 0.3251(3) -0.00506(13) 0.62421(18) 0.0140(7) Uiso 1 1 d . . . C5A C 0.6440(3) 0.06817(13) 0.59179(18) 0.0162(7) Uiso 1 1 d . . . H5A H 0.7134 0.0349 0.5914 0.019 Uiso 1 1 calc R . . H5B H 0.5799 0.0687 0.5374 0.019 Uiso 1 1 calc R . . C6A C 0.7332(3) 0.12466(12) 0.60264(19) 0.0161(7) Uiso 1 1 d . . . H6A H 0.8206 0.1183 0.6449 0.019 Uiso 1 1 calc R . . H6B H 0.7718 0.1342 0.5485 0.019 Uiso 1 1 calc R . . C7A C 0.6456(3) 0.17604(12) 0.62997(18) 0.0143(7) Uiso 1 1 d . . . C8A C 0.7058(4) 0.23132(13) 0.62862(19) 0.0196(7) Uiso 1 1 d . . . H8A H 0.7996 0.2369 0.6074 0.023 Uiso 1 1 calc R . . C9A C 0.6311(4) 0.27866(14) 0.65781(19) 0.0215(8) Uiso 1 1 d . . . H9A H 0.6731 0.3164 0.6555 0.026 Uiso 1 1 calc R . . C10A C 0.4951(4) 0.27112(14) 0.69046(19) 0.0216(8) Uiso 1 1 d . . . H10A H 0.4463 0.3032 0.7131 0.026 Uiso 1 1 calc R . . C11A C 0.4312(4) 0.21634(13) 0.68971(18) 0.0168(7) Uiso 1 1 d . . . H11A H 0.3374 0.2111 0.7110 0.020 Uiso 1 1 calc R . . C12A C 0.5034(3) 0.16888(12) 0.65803(18) 0.0140(7) Uiso 1 1 d . . . C13A C 0.2895(3) 0.10020(12) 0.62722(18) 0.0138(7) Uiso 1 1 d . . . C14A C 0.4737(3) -0.01824(12) 0.76268(18) 0.0143(7) Uiso 1 1 d . . . C15A C 0.3835(4) 0.01125(14) 0.81389(19) 0.0206(7) Uiso 1 1 d . . . H15A H 0.3272 0.0438 0.7921 0.025 Uiso 1 1 calc R . . C16A C 0.3743(4) -0.00604(14) 0.8959(2) 0.0238(8) Uiso 1 1 d . . . H16A H 0.3122 0.0145 0.9302 0.029 Uiso 1 1 calc R . . C17A C 0.4568(4) -0.05393(14) 0.9281(2) 0.0244(8) Uiso 1 1 d . . . H17A H 0.4492 -0.0666 0.9841 0.029 Uiso 1 1 calc R . . C18A C 0.5493(4) -0.08280(14) 0.8784(2) 0.0247(8) Uiso 1 1 d . . . H18A H 0.6073 -0.1148 0.9005 0.030 Uiso 1 1 calc R . . C19A C 0.5571(4) -0.06485(13) 0.79614(19) 0.0199(7) Uiso 1 1 d . . . H19A H 0.6208 -0.0849 0.7622 0.024 Uiso 1 1 calc R . . C20A C 0.1867(4) 0.14659(13) 0.60394(18) 0.0158(7) Uiso 1 1 d . . . C21A C 0.2286(3) 0.04123(12) 0.60976(17) 0.0122(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1B 0.0190(17) 0.0246(16) 0.0361(17) 0.0051(13) 0.0002(13) -0.0016(13) N2B 0.0150(16) 0.0220(16) 0.0295(16) 0.0003(13) -0.0042(12) -0.0043(13) N3B 0.0179(16) 0.0209(15) 0.0166(14) -0.0031(12) 0.0071(12) -0.0049(13) O1B 0.0153(13) 0.0285(13) 0.0258(12) -0.0066(10) 0.0007(10) -0.0095(10) O2B 0.0211(14) 0.0154(12) 0.0335(13) -0.0021(10) 0.0055(10) -0.0010(10) O1A 0.0139(13) 0.0228(13) 0.0207(11) -0.0040(9) -0.0003(9) -0.0039(9) O2A 0.0195(13) 0.0140(12) 0.0276(12) 0.0008(9) 0.0024(10) 0.0013(10) N1A 0.0191(17) 0.0215(15) 0.0294(16) -0.0034(12) -0.0025(12) -0.0006(12) N2A 0.0132(16) 0.0169(15) 0.0228(15) 0.0013(12) -0.0022(11) 0.0002(12) N3A 0.0162(16) 0.0165(15) 0.0146(13) -0.0003(11) 0.0036(11) -0.0026(12) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 N1B C20B 1.152(4) . ? N2B C21B 1.350(4) . ? N2B H2C 0.85(4) . ? N2B H2D 0.95(4) . ? N3B O2B 1.247(3) . ? N3B O1B 1.256(3) . ? N3B C4B 1.404(4) . ? C1B C13B 1.356(4) . ? C1B C12B 1.476(4) . ? C1B C2B 1.498(4) . ? C2B C3B 1.541(4) . ? C2B C5B 1.546(4) . ? C2B H2B 1.0000 . ? C3B C4B 1.505(4) . ? C3B C14B 1.533(4) . ? C3B H3B 1.0000 . ? C4B C21B 1.377(4) . ? C5B C6B 1.533(4) . ? C5B H5C 0.9900 . ? C5B H5D 0.9900 . ? C6B C7B 1.512(4) . ? C6B H6C 0.9900 . ? C6B H6D 0.9900 . ? C7B C8B 1.396(4) . ? C7B C12B 1.409(4) . ? C8B C9B 1.385(4) . ? C8B H8B 0.9500 . ? C9B C10B 1.385(5) . ? C9B H9B 0.9500 . ? C10B C11B 1.380(4) . ? C10B H10B 0.9500 . ? C11B C12B 1.406(4) . ? C11B H11B 0.9500 . ? C13B C20B 1.440(4) . ? C13B C21B 1.478(4) . ? C14B C19B 1.385(4) . ? C14B C15B 1.385(4) . ? C15B C16B 1.386(5) . ? C15B H15B 0.9500 . ? C16B C17B 1.378(5) . ? C16B H16B 0.9500 . ? C17B C18B 1.383(5) . ? C17B H17B 0.9500 . ? C18B C19B 1.390(5) . ? C18B H18B 0.9500 . ? C19B H19B 0.9500 . ? O1A N3A 1.263(3) . ? O2A N3A 1.250(3) . ? N1A C20A 1.155(4) . ? N2A C21A 1.342(4) . ? N2A H2E 0.85(3) . ? N2A H2F 0.94(3) . ? N3A C4A 1.400(4) . ? C1A C13A 1.356(4) . ? C1A C12A 1.481(4) . ? C1A C2A 1.497(4) . ? C2A C5A 1.541(4) . ? C2A C3A 1.544(4) . ? C2A H2A 1.0000 . ? C3A C4A 1.507(4) . ? C3A C14A 1.526(4) . ? C3A H3A 1.0000 . ? C4A C21A 1.379(4) . ? C5A C6A 1.529(4) . ? C5A H5A 0.9900 . ? C5A H5B 0.9900 . ? C6A C7A 1.512(4) . ? C6A H6A 0.9900 . ? C6A H6B 0.9900 . ? C7A C8A 1.385(4) . ? C7A C12A 1.409(4) . ? C8A C9A 1.388(4) . ? C8A H8A 0.9500 . ? C9A C10A 1.391(5) . ? C9A H9A 0.9500 . ? C10A C11A 1.386(4) . ? C10A H10A 0.9500 . ? C11A C12A 1.395(4) . ? C11A H11A 0.9500 . ? C13A C20A 1.436(4) . ? C13A C21A 1.481(4) . ? C14A C19A 1.384(4) . ? C14A C15A 1.390(4) . ? C15A C16A 1.380(4) . ? C15A H15A 0.9500 . ? C16A C17A 1.397(5) . ? C16A H16A 0.9500 . ? C17A C18A 1.380(5) . ? C17A H17A 0.9500 . ? C18A C19A 1.388(4) . ? C18A H18A 0.9500 . ? C19A H19A 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 C21B N2B H2C 122(2) . . ? C21B N2B H2D 115(2) . . ? H2C N2B H2D 123(3) . . ? O2B N3B O1B 120.6(2) . . ? O2B N3B C4B 118.5(3) . . ? O1B N3B C4B 120.8(3) . . ? C13B C1B C12B 124.8(3) . . ? C13B C1B C2B 120.8(3) . . ? C12B C1B C2B 113.7(3) . . ? C1B C2B C3B 115.6(3) . . ? C1B C2B C5B 104.6(2) . . ? C3B C2B C5B 114.9(2) . . ? C1B C2B H2B 107.1 . . ? C3B C2B H2B 107.1 . . ? C5B C2B H2B 107.1 . . ? C4B C3B C14B 111.3(2) . . ? C4B C3B C2B 111.9(2) . . ? C14B C3B C2B 112.1(2) . . ? C4B C3B H3B 107.1 . . ? C14B C3B H3B 107.1 . . ? C2B C3B H3B 107.1 . . ? C21B C4B N3B 120.4(3) . . ? C21B C4B C3B 123.4(3) . . ? N3B C4B C3B 116.1(3) . . ? C6B C5B C2B 109.5(2) . . ? C6B C5B H5C 109.8 . . ? C2B C5B H5C 109.8 . . ? C6B C5B H5D 109.8 . . ? C2B C5B H5D 109.8 . . ? H5C C5B H5D 108.2 . . ? C7B C6B C5B 114.4(3) . . ? C7B C6B H6C 108.7 . . ? C5B C6B H6C 108.7 . . ? C7B C6B H6D 108.7 . . ? C5B C6B H6D 108.7 . . ? H6C C6B H6D 107.6 . . ? C8B C7B C12B 118.1(3) . . ? C8B C7B C6B 120.0(3) . . ? C12B C7B C6B 121.9(3) . . ? C9B C8B C7B 121.6(3) . . ? C9B C8B H8B 119.2 . . ? C7B C8B H8B 119.2 . . ? C8B C9B C10B 119.9(3) . . ? C8B C9B H9B 120.1 . . ? C10B C9B H9B 120.1 . . ? C11B C10B C9B 120.0(3) . . ? C11B C10B H10B 120.0 . . ? C9B C10B H10B 120.0 . . ? C10B C11B C12B 120.5(3) . . ? C10B C11B H11B 119.7 . . ? C12B C11B H11B 119.7 . . ? C11B C12B C7B 119.8(3) . . ? C11B C12B C1B 122.5(3) . . ? C7B C12B C1B 117.7(3) . . ? C1B C13B C20B 121.9(3) . . ? C1B C13B C21B 122.3(3) . . ? C20B C13B C21B 115.3(3) . . ? C19B C14B C15B 118.4(3) . . ? C19B C14B C3B 120.6(3) . . ? C15B C14B C3B 121.0(3) . . ? C14B C15B C16B 121.2(3) . . ? C14B C15B H15B 119.4 . . ? C16B C15B H15B 119.4 . . ? C17B C16B C15B 120.1(3) . . ? C17B C16B H16B 119.9 . . ? C15B C16B H16B 119.9 . . ? C16B C17B C18B 119.3(3) . . ? C16B C17B H17B 120.3 . . ? C18B C17B H17B 120.3 . . ? C17B C18B C19B 120.4(3) . . ? C17B C18B H18B 119.8 . . ? C19B C18B H18B 119.8 . . ? C14B C19B C18B 120.6(3) . . ? C14B C19B H19B 119.7 . . ? C18B C19B H19B 119.7 . . ? N1B C20B C13B 175.3(3) . . ? N2B C21B C4B 125.7(3) . . ? N2B C21B C13B 116.3(3) . . ? C4B C21B C13B 117.9(3) . . ? C21A N2A H2E 119(2) . . ? C21A N2A H2F 118(2) . . ? H2E N2A H2F 123(3) . . ? O2A N3A O1A 121.0(2) . . ? O2A N3A C4A 118.7(2) . . ? O1A N3A C4A 120.3(2) . . ? C13A C1A C12A 123.4(3) . . ? C13A C1A C2A 121.2(3) . . ? C12A C1A C2A 114.8(3) . . ? C1A C2A C5A 104.4(2) . . ? C1A C2A C3A 116.1(3) . . ? C5A C2A C3A 113.9(2) . . ? C1A C2A H2A 107.3 . . ? C5A C2A H2A 107.3 . . ? C3A C2A H2A 107.3 . . ? C4A C3A C14A 109.6(2) . . ? C4A C3A C2A 112.4(2) . . ? C14A C3A C2A 111.7(2) . . ? C4A C3A H3A 107.6 . . ? C14A C3A H3A 107.6 . . ? C2A C3A H3A 107.6 . . ? C21A C4A N3A 120.9(3) . . ? C21A C4A C3A 123.4(3) . . ? N3A C4A C3A 115.4(3) . . ? C6A C5A C2A 109.7(2) . . ? C6A C5A H5A 109.7 . . ? C2A C5A H5A 109.7 . . ? C6A C5A H5B 109.7 . . ? C2A C5A H5B 109.7 . . ? H5A C5A H5B 108.2 . . ? C7A C6A C5A 114.6(3) . . ? C7A C6A H6A 108.6 . . ? C5A C6A H6A 108.6 . . ? C7A C6A H6B 108.6 . . ? C5A C6A H6B 108.6 . . ? H6A C6A H6B 107.6 . . ? C8A C7A C12A 118.8(3) . . ? C8A C7A C6A 120.0(3) . . ? C12A C7A C6A 121.2(3) . . ? C7A C8A C9A 120.9(3) . . ? C7A C8A H8A 119.5 . . ? C9A C8A H8A 119.5 . . ? C8A C9A C10A 120.3(3) . . ? C8A C9A H9A 119.9 . . ? C10A C9A H9A 119.9 . . ? C11A C10A C9A 119.4(3) . . ? C11A C10A H10A 120.3 . . ? C9A C10A H10A 120.3 . . ? C10A C11A C12A 120.6(3) . . ? C10A C11A H11A 119.7 . . ? C12A C11A H11A 119.7 . . ? C11A C12A C7A 119.8(3) . . ? C11A C12A C1A 122.3(3) . . ? C7A C12A C1A 117.9(3) . . ? C1A C13A C20A 121.9(3) . . ? C1A C13A C21A 122.7(3) . . ? C20A C13A C21A 114.8(3) . . ? C19A C14A C15A 118.6(3) . . ? C19A C14A C3A 120.9(3) . . ? C15A C14A C3A 120.6(3) . . ? C16A C15A C14A 121.0(3) . . ? C16A C15A H15A 119.5 . . ? C14A C15A H15A 119.5 . . ? C15A C16A C17A 119.7(3) . . ? C15A C16A H16A 120.2 . . ? C17A C16A H16A 120.2 . . ? C18A C17A C16A 119.8(3) . . ? C18A C17A H17A 120.1 . . ? C16A C17A H17A 120.1 . . ? C17A C18A C19A 119.7(3) . . ? C17A C18A H18A 120.1 . . ? C19A C18A H18A 120.1 . . ? C14A C19A C18A 121.2(3) . . ? C14A C19A H19A 119.4 . . ? C18A C19A H19A 119.4 . . ? N1A C20A C13A 174.3(3) . . ? N2A C21A C4A 125.6(3) . . ? N2A C21A C13A 116.7(3) . . ? C4A C21A C13A 117.7(3) . . ? data_05jo0031_0m _database_code_depnum_ccdc_archive 'CCDC 285437' _audit_creation_date 2005-07-26T15:37:08-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C21 H16 Br1 N3 O2' _chemical_formula_sum 'C21 H16 Br N3 O2' _chemical_formula_weight 422.28 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration ad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_Int_Tables_number 19 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' _cell_length_a 6.7062(5) _cell_length_b 12.4969(10) _cell_length_c 22.780(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1909.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5992 _cell_measurement_theta_min 2.417 _cell_measurement_theta_max 25.46 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.469 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 2.174 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0425 _diffrn_reflns_av_unetI/netI 0.0398 _diffrn_reflns_number 38312 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 30.5 _diffrn_reflns_theta_full 30.5 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _reflns_number_total 5814 _reflns_number_gt 4354 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Apex2 (Bruker-Nonius, 2004)' _computing_cell_refinement 'Saint+ (Bruker-Nonius, 2004)' _computing_data_reduction 'Saint+ (Bruker-Nonius, 2004)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0249P)^2^+0.3809P] 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_number_reflns 5814 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0605 _refine_ls_R_factor_gt 0.0326 _refine_ls_wR_factor_ref 0.0644 _refine_ls_wR_factor_gt 0.059 _refine_ls_goodness_of_fit_ref 1.02 _refine_ls_restrained_S_all 1.02 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.011(6) _refine_diff_density_max 0.531 _refine_diff_density_min -0.604 _refine_diff_density_rms 0.055 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 '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' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 -0.03492(4) 0.802973(17) 0.952351(9) 0.04706(8) Uani 1 1 d . . . N3 N 0.3695(2) 1.13404(14) 0.73361(7) 0.0307(4) Uani 1 1 d . . . O1 O 0.5122(2) 1.07915(12) 0.74553(7) 0.0482(4) Uani 1 1 d . . . O2 O 0.3488(2) 1.22687(12) 0.74901(8) 0.0482(4) Uani 1 1 d . . . N1 N -0.0245(3) 1.03071(14) 0.45312(8) 0.0404(4) Uani 1 1 d . . . N2 N -0.3579(3) 1.09298(14) 0.61126(8) 0.0394(4) Uani 1 1 d . . . C1 C 0.0809(2) 0.94477(13) 0.59801(7) 0.0215(4) Uani 1 1 d . . . C2 C 0.0318(3) 0.92063(14) 0.66120(7) 0.0238(3) Uani 1 1 d . . . H2 H -0.1018 0.9516 0.6707 0.029 Uiso 1 1 calc R . . C3 C 0.1889(3) 0.96656(15) 0.70466(8) 0.0230(4) Uani 1 1 d . . . H3 H 0.3210 0.9339 0.6950 0.028 Uiso 1 1 calc R . . C4 C 0.2060(3) 1.08740(15) 0.69622(8) 0.0280(4) Uani 1 1 d . . . H4A H 0.2337 1.1031 0.6544 0.034 Uiso 1 1 calc R . . H4B H 0.0776 1.1215 0.7066 0.034 Uiso 1 1 calc R . . C5 C 0.0198(3) 0.79763(16) 0.66522(8) 0.0327(4) Uani 1 1 d . . . H5A H -0.0211 0.7770 0.7054 0.039 Uiso 1 1 calc R . . H5B H -0.0831 0.7713 0.6376 0.039 Uiso 1 1 calc R . . C6 C 0.2180(3) 0.74500(16) 0.65083(9) 0.0362(5) Uani 1 1 d . . . H6A H 0.3043 0.7475 0.6861 0.043 Uiso 1 1 calc R . . H6B H 0.1941 0.6688 0.6413 0.043 Uiso 1 1 calc R . . C7 C 0.3265(3) 0.79636(16) 0.60054(8) 0.0278(4) Uani 1 1 d . . . C8 C 0.4997(3) 0.74883(16) 0.57856(9) 0.0380(5) Uani 1 1 d . . . H8 H 0.5473 0.6847 0.5960 0.046 Uiso 1 1 calc R . . C9 C 0.6028(3) 0.79261(19) 0.53233(9) 0.0409(5) Uani 1 1 d . . . H9 H 0.7195 0.7584 0.5180 0.049 Uiso 1 1 calc R . . C10 C 0.5365(3) 0.88676(16) 0.50664(9) 0.0350(5) Uani 1 1 d . . . H10 H 0.6061 0.9164 0.4741 0.042 Uiso 1 1 calc R . . C11 C 0.3706(3) 0.93687(16) 0.52825(8) 0.0285(4) Uani 1 1 d . . . H11 H 0.3292 1.0029 0.5116 0.034 Uiso 1 1 calc R . . C12 C 0.2605(3) 0.89245(14) 0.57463(8) 0.0228(4) Uani 1 1 d . . . C13 C -0.0451(3) 1.00592(13) 0.56560(7) 0.0232(3) Uani 1 1 d . . . C14 C 0.1359(3) 0.93539(14) 0.76712(8) 0.0233(4) Uani 1 1 d . . . C15 C -0.0499(3) 0.95781(15) 0.79133(8) 0.0296(4) Uani 1 1 d . . . H15 H -0.1429 0.9993 0.7696 0.036 Uiso 1 1 calc R . . C16 C -0.1016(3) 0.92049(16) 0.84670(9) 0.0320(4) Uani 1 1 d . . . H16 H -0.2293 0.9354 0.8628 0.038 Uiso 1 1 calc R . . C17 C 0.0354(3) 0.86160(14) 0.87782(8) 0.0319(4) Uani 1 1 d . . . C18 C 0.2240(3) 0.84162(15) 0.85620(9) 0.0327(5) Uani 1 1 d . . . H18 H 0.3187 0.8033 0.8790 0.039 Uiso 1 1 calc R . . C19 C 0.2728(3) 0.87851(15) 0.80068(8) 0.0288(4) Uani 1 1 d . . . H19 H 0.4019 0.8647 0.7853 0.035 Uiso 1 1 calc R . . C20 C -0.0290(3) 1.02045(14) 0.50298(8) 0.0270(4) Uani 1 1 d . . . C21 C -0.2181(3) 1.05506(15) 0.59129(8) 0.0273(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 Br1 0.07939(16) 0.03803(11) 0.02375(10) 0.00492(9) 0.01325(10) 0.00986(11) N3 0.0280(9) 0.0373(10) 0.0268(9) -0.0042(8) 0.0031(7) -0.0070(8) O1 0.0353(8) 0.0493(9) 0.0601(10) -0.0052(8) -0.0196(7) -0.0001(8) O2 0.0412(9) 0.0395(9) 0.0638(12) -0.0183(8) 0.0057(8) -0.0092(7) N1 0.0397(9) 0.0536(10) 0.0280(9) 0.0066(8) -0.0021(9) -0.0030(8) N2 0.0336(10) 0.0384(10) 0.0461(11) -0.0082(8) 0.0023(8) 0.0049(8) C1 0.0223(9) 0.0224(8) 0.0199(9) -0.0018(7) -0.0007(7) -0.0068(7) C2 0.0217(8) 0.0324(9) 0.0173(8) 0.0003(7) -0.0009(7) -0.0008(8) C3 0.0210(9) 0.0295(9) 0.0184(9) -0.0017(7) -0.0003(7) 0.0007(7) C4 0.0268(9) 0.0341(10) 0.0230(10) -0.0016(8) -0.0030(8) -0.0004(8) C5 0.0395(11) 0.0366(10) 0.0221(8) 0.0046(8) -0.0040(8) -0.0120(10) C6 0.0518(13) 0.0271(10) 0.0297(11) 0.0013(9) -0.0088(10) -0.0024(9) C7 0.0312(10) 0.0264(9) 0.0259(9) -0.0068(8) -0.0073(7) -0.0002(8) C8 0.0367(13) 0.0357(10) 0.0416(12) -0.0143(9) -0.0116(10) 0.0102(9) C9 0.0261(10) 0.0539(13) 0.0428(13) -0.0289(11) -0.0044(8) 0.0067(10) C10 0.0228(9) 0.0514(12) 0.0309(10) -0.0161(9) 0.0028(9) -0.0047(10) C11 0.0256(9) 0.0356(10) 0.0243(10) -0.0051(8) -0.0020(8) -0.0063(8) C12 0.0204(9) 0.0264(9) 0.0215(9) -0.0065(7) -0.0017(7) -0.0019(7) C13 0.0231(8) 0.0255(8) 0.0209(8) -0.0023(6) 0.0001(7) -0.0024(8) C14 0.0260(9) 0.0256(9) 0.0184(9) -0.0022(7) -0.0002(7) 0.0014(7) C15 0.0309(10) 0.0356(9) 0.0223(9) 0.0012(8) -0.0015(8) 0.0074(9) C16 0.0346(11) 0.0364(11) 0.0251(10) -0.0034(8) 0.0089(8) 0.0057(9) C17 0.0522(12) 0.0248(9) 0.0185(9) -0.0020(7) 0.0037(9) 0.0005(10) C18 0.0420(12) 0.0305(10) 0.0256(10) 0.0023(8) -0.0046(9) 0.0073(9) C19 0.0277(10) 0.0337(10) 0.0251(10) -0.0020(8) -0.0027(8) 0.0042(8) C20 0.0248(9) 0.0300(9) 0.0262(10) 0.0026(7) -0.0021(8) -0.0015(8) C21 0.0305(10) 0.0270(10) 0.0243(10) -0.0017(8) -0.0037(8) -0.0004(8) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 Br1 C17 1.9082(18) . ? N3 O1 1.208(2) . ? N3 O2 1.220(2) . ? N3 C4 1.506(2) . ? N1 C20 1.143(2) . ? N2 C21 1.145(3) . ? C1 C13 1.358(2) . ? C1 C12 1.470(2) . ? C1 C2 1.507(2) . ? C2 C5 1.542(3) . ? C2 C3 1.556(2) . ? C2 H2 1.0000 . ? C3 C14 1.517(2) . ? C3 C4 1.527(3) . ? C3 H3 1.0000 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.519(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.501(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.397(3) . ? C7 C12 1.409(3) . ? C8 C9 1.373(3) . ? C8 H8 0.9500 . ? C9 C10 1.387(3) . ? C9 H9 0.9500 . ? C10 C11 1.368(3) . ? C10 H10 0.9500 . ? C11 C12 1.404(3) . ? C11 H11 0.9500 . ? C13 C21 1.437(3) . ? C13 C20 1.442(2) . ? C14 C19 1.390(3) . ? C14 C15 1.391(3) . ? C15 C16 1.389(3) . ? C15 H15 0.9500 . ? C16 C17 1.374(3) . ? C16 H16 0.9500 . ? C17 C18 1.380(3) . ? C18 C19 1.385(3) . ? C18 H18 0.9500 . ? C19 H19 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 O1 N3 O2 124.40(18) . . ? O1 N3 C4 118.95(16) . . ? O2 N3 C4 116.63(18) . . ? C13 C1 C12 124.29(16) . . ? C13 C1 C2 119.73(16) . . ? C12 C1 C2 115.84(15) . . ? C1 C2 C5 105.52(14) . . ? C1 C2 C3 112.71(15) . . ? C5 C2 C3 111.43(15) . . ? C1 C2 H2 109.0 . . ? C5 C2 H2 109.0 . . ? C3 C2 H2 109.0 . . ? C14 C3 C4 112.93(15) . . ? C14 C3 C2 110.08(14) . . ? C4 C3 C2 109.61(14) . . ? C14 C3 H3 108.0 . . ? C4 C3 H3 108.0 . . ? C2 C3 H3 108.0 . . ? N3 C4 C3 111.49(15) . . ? N3 C4 H4A 109.3 . . ? C3 C4 H4A 109.3 . . ? N3 C4 H4B 109.3 . . ? C3 C4 H4B 109.3 . . ? H4A C4 H4B 108.0 . . ? C6 C5 C2 111.91(15) . . ? C6 C5 H5A 109.2 . . ? C2 C5 H5A 109.2 . . ? C6 C5 H5B 109.2 . . ? C2 C5 H5B 109.2 . . ? H5A C5 H5B 107.9 . . ? C7 C6 C5 113.82(16) . . ? C7 C6 H6A 108.8 . . ? C5 C6 H6A 108.8 . . ? C7 C6 H6B 108.8 . . ? C5 C6 H6B 108.8 . . ? H6A C6 H6B 107.7 . . ? C8 C7 C12 118.25(18) . . ? C8 C7 C6 119.65(18) . . ? C12 C7 C6 122.10(17) . . ? C9 C8 C7 121.6(2) . . ? C9 C8 H8 119.2 . . ? C7 C8 H8 119.2 . . ? C8 C9 C10 119.99(18) . . ? C8 C9 H9 120.0 . . ? C10 C9 H9 120.0 . . ? C11 C10 C9 119.80(19) . . ? C11 C10 H10 120.1 . . ? C9 C10 H10 120.1 . . ? C10 C11 C12 121.2(2) . . ? C10 C11 H11 119.4 . . ? C12 C11 H11 119.4 . . ? C11 C12 C7 119.13(17) . . ? C11 C12 C1 121.85(17) . . ? C7 C12 C1 119.00(16) . . ? C1 C13 C21 121.44(16) . . ? C1 C13 C20 124.19(17) . . ? C21 C13 C20 114.19(16) . . ? C19 C14 C15 118.46(17) . . ? C19 C14 C3 119.48(16) . . ? C15 C14 C3 122.00(16) . . ? C16 C15 C14 121.06(17) . . ? C16 C15 H15 119.5 . . ? C14 C15 H15 119.5 . . ? C17 C16 C15 118.81(18) . . ? C17 C16 H16 120.6 . . ? C15 C16 H16 120.6 . . ? C16 C17 C18 121.69(17) . . ? C16 C17 Br1 119.99(16) . . ? C18 C17 Br1 118.32(15) . . ? C17 C18 C19 118.81(18) . . ? C17 C18 H18 120.6 . . ? C19 C18 H18 120.6 . . ? C18 C19 C14 121.08(18) . . ? C18 C19 H19 119.5 . . ? C14 C19 H19 119.5 . . ? N1 C20 C13 177.1(2) . . ? N2 C21 C13 178.8(2) . . ? 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 C13 C1 C2 C5 120.78(18) . . . . ? C12 C1 C2 C5 -55.13(19) . . . . ? C13 C1 C2 C3 -117.40(18) . . . . ? C12 C1 C2 C3 66.70(19) . . . . ? C1 C2 C3 C14 -177.50(15) . . . . ? C5 C2 C3 C14 -59.08(19) . . . . ? C1 C2 C3 C4 57.70(19) . . . . ? C5 C2 C3 C4 176.12(15) . . . . ? O1 N3 C4 C3 29.6(2) . . . . ? O2 N3 C4 C3 -151.63(18) . . . . ? C14 C3 C4 N3 61.9(2) . . . . ? C2 C3 C4 N3 -174.93(14) . . . . ? C1 C2 C5 C6 62.66(19) . . . . ? C3 C2 C5 C6 -59.99(19) . . . . ? C2 C5 C6 C7 -40.3(2) . . . . ? C5 C6 C7 C8 -172.96(16) . . . . ? C5 C6 C7 C12 7.6(3) . . . . ? C12 C7 C8 C9 -1.0(3) . . . . ? C6 C7 C8 C9 179.50(18) . . . . ? C7 C8 C9 C10 0.6(3) . . . . ? C8 C9 C10 C11 1.3(3) . . . . ? C9 C10 C11 C12 -2.7(3) . . . . ? C10 C11 C12 C7 2.2(3) . . . . ? C10 C11 C12 C1 -179.44(16) . . . . ? C8 C7 C12 C11 -0.3(3) . . . . ? C6 C7 C12 C11 179.14(17) . . . . ? C8 C7 C12 C1 -178.73(16) . . . . ? C6 C7 C12 C1 0.7(3) . . . . ? C13 C1 C12 C11 31.0(3) . . . . ? C2 C1 C12 C11 -153.32(16) . . . . ? C13 C1 C12 C7 -150.63(17) . . . . ? C2 C1 C12 C7 25.1(2) . . . . ? C12 C1 C13 C21 -179.83(16) . . . . ? C2 C1 C13 C21 4.6(3) . . . . ? C12 C1 C13 C20 5.4(3) . . . . ? C2 C1 C13 C20 -170.15(16) . . . . ? C4 C3 C14 C19 -114.61(19) . . . . ? C2 C3 C14 C19 122.53(18) . . . . ? C4 C3 C14 C15 68.3(2) . . . . ? C2 C3 C14 C15 -54.6(2) . . . . ? C19 C14 C15 C16 -2.8(3) . . . . ? C3 C14 C15 C16 174.33(18) . . . . ? C14 C15 C16 C17 0.7(3) . . . . ? C15 C16 C17 C18 2.0(3) . . . . ? C15 C16 C17 Br1 -176.89(14) . . . . ? C16 C17 C18 C19 -2.6(3) . . . . ? Br1 C17 C18 C19 176.31(14) . . . . ? C17 C18 C19 C14 0.5(3) . . . . ? C15 C14 C19 C18 2.2(3) . . . . ? C3 C14 C19 C18 -175.02(17) . . . . ? C1 C13 C20 N1 127(4) . . . . ? C21 C13 C20 N1 -48(4) . . . . ? C1 C13 C21 N2 -108(12) . . . . ? C20 C13 C21 N2 67(12) . . . . ?