####################################################################### # # 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_7 _database_code_depnum_ccdc_archive 'CCDC 737646' # start Validation Reply Form _vrf_PLAT029_7 ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.92 RESPONSE: Fit for purpose. ; _vrf_PLAT029_18 ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.93 RESPONSE: Fit for purpose. ; # end Validation Reply Form _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H16 N2 O' _chemical_formula_sum 'C19 H16 N2 O' _chemical_formula_weight 288.34 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.803(2) _cell_length_b 11.370(3) _cell_length_c 14.533(3) _cell_angle_alpha 69.857(9) _cell_angle_beta 76.385(9) _cell_angle_gamma 75.170(11) _cell_volume 1450.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 5898 _cell_measurement_theta_min 1.50 _cell_measurement_theta_max 27.58 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.320 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9123 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type ccd _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8213 _diffrn_reflns_av_R_equivalents 0.0517 _diffrn_reflns_av_sigmaI/netI 0.0435 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 25.34 _reflns_number_total 4769 _reflns_number_gt 3810 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _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^)+(0.0805P)^2^+1.8225P] 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 4769 _refine_ls_number_parameters 400 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0866 _refine_ls_R_factor_gt 0.0663 _refine_ls_wR_factor_ref 0.1717 _refine_ls_wR_factor_gt 0.1555 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _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 C1A C 0.4630(3) 0.4618(3) 0.6331(2) 0.0208(6) Uani 1 1 d . . . C1 C 0.4486(3) 0.3334(3) 0.6646(2) 0.0251(7) Uani 1 1 d . . . H1A H 0.5317 0.2685 0.6640 0.030 Uiso 1 1 calc R . . C2 C 0.3156(3) 0.3001(3) 0.6963(2) 0.0272(7) Uani 1 1 d . . . H2A H 0.3072 0.2129 0.7181 0.033 Uiso 1 1 calc R . . C3 C 0.1940(3) 0.3957(3) 0.6960(2) 0.0268(7) Uani 1 1 d . . . H3A H 0.1022 0.3732 0.7173 0.032 Uiso 1 1 calc R . . C4 C 0.2044(3) 0.5234(3) 0.6651(2) 0.0238(6) Uani 1 1 d . . . H4A H 0.1203 0.5874 0.6655 0.029 Uiso 1 1 calc R . . C4A C 0.3391(3) 0.5579(3) 0.63325(19) 0.0201(6) Uani 1 1 d . . . N5 N 0.3477(2) 0.6892(2) 0.59712(16) 0.0188(5) Uani 1 1 d . . . C5 C 0.2218(3) 0.7859(3) 0.5664(2) 0.0231(6) Uani 1 1 d . . . H5A H 0.2511 0.8677 0.5283 0.035 Uiso 1 1 calc R . . H5B H 0.1526 0.7956 0.6254 0.035 Uiso 1 1 calc R . . H5C H 0.1777 0.7590 0.5250 0.035 Uiso 1 1 calc R . . C5A C 0.4795(3) 0.7219(3) 0.56525(19) 0.0177(6) Uani 1 1 d . . . N6 N 0.5031(2) 0.8332(2) 0.50758(16) 0.0191(5) Uani 1 1 d . . . C6A C 0.6547(3) 0.8196(3) 0.48593(19) 0.0188(6) Uani 1 1 d . . . C7 C 0.7305(3) 0.9120(3) 0.4206(2) 0.0217(6) Uani 1 1 d . . . H7A H 0.6828 0.9962 0.3909 0.026 Uiso 1 1 calc R . . C8 C 0.8792(3) 0.8768(3) 0.4002(2) 0.0232(6) Uani 1 1 d . . . H8A H 0.9336 0.9379 0.3558 0.028 Uiso 1 1 calc R . . C9 C 0.9488(3) 0.7531(3) 0.4442(2) 0.0238(7) Uani 1 1 d . . . H9A H 1.0497 0.7306 0.4276 0.029 Uiso 1 1 calc R . . C10 C 0.8731(3) 0.6621(3) 0.5119(2) 0.0213(6) Uani 1 1 d . . . H10A H 0.9213 0.5790 0.5435 0.026 Uiso 1 1 calc R . . C10B C 0.6110(3) 0.6264(3) 0.59967(19) 0.0181(6) Uani 1 1 d . . . C10A C 0.7254(3) 0.6963(3) 0.53206(19) 0.0196(6) Uani 1 1 d . . . C11 C 0.6075(3) 0.4933(3) 0.60047(19) 0.0207(6) Uani 1 1 d . . . O11 O 0.7151(2) 0.4173(2) 0.58181(15) 0.0263(5) Uani 1 1 d . . . C12 C 0.6074(3) 0.6177(3) 0.71113(19) 0.0204(6) Uani 1 1 d . . . H12A H 0.6060 0.7036 0.7142 0.025 Uiso 1 1 calc R . . H12B H 0.5179 0.5907 0.7515 0.025 Uiso 1 1 calc R . . C13 C 0.7313(3) 0.5271(3) 0.7551(2) 0.0224(6) Uani 1 1 d . . . H13A H 0.7409 0.4394 0.7616 0.027 Uiso 1 1 calc R . . C14 C 0.8284(3) 0.5593(3) 0.7856(2) 0.0304(7) Uani 1 1 d . . . H14A H 0.8224 0.6461 0.7803 0.037 Uiso 1 1 calc R . . H14B H 0.9046 0.4959 0.8129 0.037 Uiso 1 1 calc R . . C21A C 1.0124(3) 0.8391(3) 1.05828(19) 0.0202(6) Uani 1 1 d . . . C21 C 1.0218(3) 0.8606(3) 1.1464(2) 0.0217(6) Uani 1 1 d . . . H21A H 0.9367 0.8889 1.1865 0.026 Uiso 1 1 calc R . . C22 C 1.1520(3) 0.8415(3) 1.1757(2) 0.0244(7) Uani 1 1 d . . . H22A H 1.1564 0.8544 1.2361 0.029 Uiso 1 1 calc R . . C23 C 1.2765(3) 0.8031(3) 1.1157(2) 0.0250(7) Uani 1 1 d . . . H23A H 1.3665 0.7918 1.1346 0.030 Uiso 1 1 calc R . . C24 C 1.2713(3) 0.7812(3) 1.0288(2) 0.0230(6) Uani 1 1 d . . . H24A H 1.3576 0.7543 0.9891 0.028 Uiso 1 1 calc R . . C24A C 1.1403(3) 0.7981(3) 0.9989(2) 0.0203(6) Uani 1 1 d . . . N25 N 1.1362(2) 0.7800(2) 0.90802(16) 0.0209(5) Uani 1 1 d . . . C25 C 1.2684(3) 0.7660(3) 0.8362(2) 0.0286(7) Uani 1 1 d . . . H25A H 1.2485 0.7451 0.7813 0.043 Uiso 1 1 calc R . . H25B H 1.3407 0.6974 0.8693 0.043 Uiso 1 1 calc R . . H25C H 1.3040 0.8463 0.8104 0.043 Uiso 1 1 calc R . . C25A C 1.0086(3) 0.8116(3) 0.8747(2) 0.0192(6) Uani 1 1 d . . . N26 N 0.9942(2) 0.8422(2) 0.78233(16) 0.0202(5) Uani 1 1 d . . . C26A C 0.8445(3) 0.8798(3) 0.78146(19) 0.0196(6) Uani 1 1 d . . . C27 C 0.7783(3) 0.9285(3) 0.6983(2) 0.0247(7) Uani 1 1 d . . . H27A H 0.8325 0.9325 0.6342 0.030 Uiso 1 1 calc R . . C28 C 0.6310(3) 0.9714(3) 0.7103(2) 0.0258(7) Uani 1 1 d . . . H28A H 0.5840 1.0058 0.6539 0.031 Uiso 1 1 calc R . . C29 C 0.5514(3) 0.9644(3) 0.8052(2) 0.0263(7) Uani 1 1 d . . . H29A H 0.4512 0.9959 0.8123 0.032 Uiso 1 1 calc R . . C30 C 0.6179(3) 0.9117(3) 0.8894(2) 0.0222(6) Uani 1 1 d . . . H30A H 0.5633 0.9044 0.9538 0.027 Uiso 1 1 calc R . . C30B C 0.8700(3) 0.8074(3) 0.94871(19) 0.0184(6) Uani 1 1 d . . . C30A C 0.7643(3) 0.8702(3) 0.87736(19) 0.0195(6) Uani 1 1 d . . . C31 C 0.8701(3) 0.8636(3) 1.02976(19) 0.0198(6) Uani 1 1 d . . . O31 O 0.7607(2) 0.91595(19) 1.07144(14) 0.0242(5) Uani 1 1 d . . . C32 C 0.8614(3) 0.6618(3) 1.0012(2) 0.0215(6) Uani 1 1 d . . . H32A H 0.8837 0.6179 0.9498 0.026 Uiso 1 1 calc R . . H32B H 0.9353 0.6224 1.0448 0.026 Uiso 1 1 calc R . . C33 C 0.7184(3) 0.6407(3) 1.0620(2) 0.0240(7) Uani 1 1 d . . . H33A H 0.6858 0.6729 1.1172 0.029 Uiso 1 1 calc R . . C34 C 0.6354(3) 0.5801(3) 1.0431(2) 0.0298(7) Uani 1 1 d . . . H34A H 0.6652 0.5469 0.9884 0.036 Uiso 1 1 calc R . . H34B H 0.5457 0.5697 1.0843 0.036 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 C1A 0.0251(15) 0.0233(16) 0.0157(13) -0.0079(11) -0.0001(11) -0.0080(12) C1 0.0333(17) 0.0259(17) 0.0192(14) -0.0102(12) -0.0014(13) -0.0088(13) C2 0.0377(18) 0.0284(17) 0.0186(14) -0.0061(12) -0.0017(13) -0.0156(14) C3 0.0275(16) 0.0367(18) 0.0205(14) -0.0090(13) 0.0018(12) -0.0185(14) C4 0.0221(15) 0.0324(17) 0.0198(14) -0.0109(12) 0.0006(12) -0.0097(13) C4A 0.0226(15) 0.0261(16) 0.0132(12) -0.0066(11) 0.0003(11) -0.0093(12) N5 0.0143(11) 0.0206(13) 0.0210(12) -0.0071(10) 0.0004(9) -0.0044(9) C5 0.0170(14) 0.0295(17) 0.0229(14) -0.0068(12) -0.0042(12) -0.0051(12) C5A 0.0187(14) 0.0228(15) 0.0135(12) -0.0074(11) -0.0015(11) -0.0056(11) N6 0.0171(12) 0.0227(13) 0.0184(11) -0.0071(10) -0.0003(9) -0.0065(10) C6A 0.0180(14) 0.0230(15) 0.0173(13) -0.0086(11) -0.0016(11) -0.0050(11) C7 0.0237(15) 0.0256(16) 0.0191(13) -0.0072(12) -0.0022(12) -0.0110(12) C8 0.0222(15) 0.0290(17) 0.0206(14) -0.0087(12) 0.0026(12) -0.0127(13) C9 0.0160(14) 0.0409(19) 0.0212(14) -0.0161(13) 0.0010(11) -0.0118(13) C10 0.0193(14) 0.0301(17) 0.0187(13) -0.0125(12) -0.0023(11) -0.0054(12) C10B 0.0169(14) 0.0227(15) 0.0153(13) -0.0051(11) -0.0027(11) -0.0059(11) C10A 0.0206(14) 0.0271(16) 0.0148(13) -0.0101(11) -0.0005(11) -0.0079(12) C11 0.0251(16) 0.0244(16) 0.0139(13) -0.0062(11) -0.0035(11) -0.0061(13) O11 0.0249(11) 0.0278(12) 0.0264(11) -0.0121(9) -0.0017(9) -0.0022(9) C12 0.0202(14) 0.0242(16) 0.0183(13) -0.0066(11) 0.0002(11) -0.0093(12) C13 0.0280(16) 0.0212(15) 0.0178(13) -0.0054(11) -0.0036(12) -0.0054(12) C14 0.0301(17) 0.0340(19) 0.0272(16) -0.0069(13) -0.0092(13) -0.0052(14) C21A 0.0231(15) 0.0203(15) 0.0158(13) -0.0021(11) 0.0006(11) -0.0099(12) C21 0.0264(15) 0.0204(15) 0.0179(13) -0.0020(11) -0.0011(12) -0.0113(12) C22 0.0320(17) 0.0263(17) 0.0190(14) -0.0050(12) -0.0046(12) -0.0146(13) C23 0.0253(16) 0.0232(16) 0.0271(15) -0.0026(12) -0.0057(13) -0.0110(13) C24 0.0224(15) 0.0234(16) 0.0210(14) -0.0029(12) -0.0004(12) -0.0086(12) C24A 0.0229(15) 0.0183(15) 0.0186(13) -0.0032(11) -0.0008(11) -0.0078(11) N25 0.0171(12) 0.0282(14) 0.0183(11) -0.0087(10) 0.0010(9) -0.0069(10) C25 0.0195(15) 0.043(2) 0.0241(15) -0.0157(14) 0.0035(12) -0.0067(14) C25A 0.0187(14) 0.0191(15) 0.0192(13) -0.0054(11) 0.0010(11) -0.0068(11) N26 0.0206(12) 0.0204(13) 0.0182(11) -0.0043(9) -0.0003(9) -0.0062(10) C26A 0.0225(14) 0.0180(14) 0.0179(13) -0.0040(11) 0.0005(11) -0.0090(11) C27 0.0288(16) 0.0265(17) 0.0183(14) -0.0036(12) 0.0000(12) -0.0127(13) C28 0.0279(16) 0.0269(17) 0.0231(15) -0.0007(12) -0.0110(13) -0.0093(13) C29 0.0219(15) 0.0263(17) 0.0310(16) -0.0067(13) -0.0038(13) -0.0087(13) C30 0.0223(15) 0.0223(15) 0.0214(14) -0.0055(12) 0.0013(12) -0.0095(12) C30B 0.0183(14) 0.0208(15) 0.0142(12) -0.0018(11) -0.0004(11) -0.0074(11) C30A 0.0234(15) 0.0181(15) 0.0169(13) -0.0037(11) 0.0013(11) -0.0102(12) C31 0.0214(15) 0.0204(15) 0.0154(13) -0.0013(11) 0.0016(11) -0.0099(12) O31 0.0219(11) 0.0282(12) 0.0207(10) -0.0088(9) 0.0037(8) -0.0065(9) C32 0.0250(15) 0.0201(15) 0.0191(13) -0.0045(11) -0.0029(12) -0.0069(12) C33 0.0304(16) 0.0228(16) 0.0174(13) -0.0026(12) 0.0009(12) -0.0118(13) C34 0.0295(17) 0.0317(18) 0.0262(16) -0.0053(13) 0.0032(13) -0.0142(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1A C1 1.406(4) . ? C1A C4A 1.410(4) . ? C1A C11 1.478(4) . ? C1 C2 1.380(4) . ? C1 H1A 0.9500 . ? C2 C3 1.393(5) . ? C2 H2A 0.9500 . ? C3 C4 1.388(4) . ? C3 H3A 0.9500 . ? C4 C4A 1.402(4) . ? C4 H4A 0.9500 . ? C4A N5 1.419(4) . ? N5 C5A 1.367(3) . ? N5 C5 1.470(4) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C5A N6 1.298(4) . ? C5A C10B 1.518(4) . ? N6 C6A 1.424(4) . ? C6A C7 1.393(4) . ? C6A C10A 1.403(4) . ? C7 C8 1.397(4) . ? C7 H7A 0.9500 . ? C8 C9 1.395(4) . ? C8 H8A 0.9500 . ? C9 C10 1.392(4) . ? C9 H9A 0.9500 . ? C10 C10A 1.387(4) . ? C10 H10A 0.9500 . ? C10B C10A 1.502(4) . ? C10B C11 1.518(4) . ? C10B C12 1.581(4) . ? C11 O11 1.222(4) . ? C12 C13 1.489(4) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.313(4) . ? C13 H13A 0.9500 . ? C14 H14A 0.9500 . ? C14 H14B 0.9500 . ? C21A C21 1.412(4) . ? C21A C24A 1.416(4) . ? C21A C31 1.479(4) . ? C21 C22 1.381(4) . ? C21 H21A 0.9500 . ? C22 C23 1.388(4) . ? C22 H22A 0.9500 . ? C23 C24 1.383(4) . ? C23 H23A 0.9500 . ? C24 C24A 1.397(4) . ? C24 H24A 0.9500 . ? C24A N25 1.416(4) . ? N25 C25A 1.365(4) . ? N25 C25 1.471(4) . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C25A N26 1.298(4) . ? C25A C30B 1.522(4) . ? N26 C26A 1.421(4) . ? C26A C27 1.383(4) . ? C26A C30A 1.413(4) . ? C27 C28 1.390(4) . ? C27 H27A 0.9500 . ? C28 C29 1.402(4) . ? C28 H28A 0.9500 . ? C29 C30 1.397(4) . ? C29 H29A 0.9500 . ? C30 C30A 1.380(4) . ? C30 H30A 0.9500 . ? C30B C30A 1.509(4) . ? C30B C31 1.521(4) . ? C30B C32 1.582(4) . ? C31 O31 1.220(3) . ? C32 C33 1.499(4) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 C34 1.317(4) . ? C33 H33A 0.9500 . ? C34 H34A 0.9500 . ? C34 H34B 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 C1A C4A 119.2(3) . . ? C1 C1A C11 119.3(3) . . ? C4A C1A C11 121.4(3) . . ? C2 C1 C1A 121.1(3) . . ? C2 C1 H1A 119.4 . . ? C1A C1 H1A 119.4 . . ? C1 C2 C3 119.2(3) . . ? C1 C2 H2A 120.4 . . ? C3 C2 H2A 120.4 . . ? C4 C3 C2 121.1(3) . . ? C4 C3 H3A 119.4 . . ? C2 C3 H3A 119.4 . . ? C3 C4 C4A 119.9(3) . . ? C3 C4 H4A 120.0 . . ? C4A C4 H4A 120.0 . . ? C4 C4A C1A 119.4(3) . . ? C4 C4A N5 119.2(3) . . ? C1A C4A N5 121.3(2) . . ? C5A N5 C4A 118.8(2) . . ? C5A N5 C5 118.8(2) . . ? C4A N5 C5 119.9(2) . . ? N5 C5 H5A 109.5 . . ? N5 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N5 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N6 C5A N5 124.6(3) . . ? N6 C5A C10B 115.2(2) . . ? N5 C5A C10B 120.2(2) . . ? C5A N6 C6A 105.1(2) . . ? C7 C6A C10A 121.2(3) . . ? C7 C6A N6 125.9(3) . . ? C10A C6A N6 112.8(2) . . ? C6A C7 C8 117.8(3) . . ? C6A C7 H7A 121.1 . . ? C8 C7 H7A 121.1 . . ? C9 C8 C7 120.9(3) . . ? C9 C8 H8A 119.6 . . ? C7 C8 H8A 119.6 . . ? C10 C9 C8 121.2(3) . . ? C10 C9 H9A 119.4 . . ? C8 C9 H9A 119.4 . . ? C10A C10 C9 118.1(3) . . ? C10A C10 H10A 120.9 . . ? C9 C10 H10A 120.9 . . ? C10A C10B C5A 99.6(2) . . ? C10A C10B C11 120.8(2) . . ? C5A C10B C11 111.6(2) . . ? C10A C10B C12 110.5(2) . . ? C5A C10B C12 107.3(2) . . ? C11 C10B C12 106.3(2) . . ? C10 C10A C6A 120.8(3) . . ? C10 C10A C10B 133.2(3) . . ? C6A C10A C10B 106.0(2) . . ? O11 C11 C1A 123.5(3) . . ? O11 C11 C10B 123.0(3) . . ? C1A C11 C10B 113.4(2) . . ? C13 C12 C10B 113.4(2) . . ? C13 C12 H12A 108.9 . . ? C10B C12 H12A 108.9 . . ? C13 C12 H12B 108.9 . . ? C10B C12 H12B 108.9 . . ? H12A C12 H12B 107.7 . . ? C14 C13 C12 124.9(3) . . ? C14 C13 H13A 117.6 . . ? C12 C13 H13A 117.6 . . ? C13 C14 H14A 120.0 . . ? C13 C14 H14B 120.0 . . ? H14A C14 H14B 120.0 . . ? C21 C21A C24A 118.5(3) . . ? C21 C21A C31 119.1(2) . . ? C24A C21A C31 122.3(3) . . ? C22 C21 C21A 121.5(3) . . ? C22 C21 H21A 119.2 . . ? C21A C21 H21A 119.2 . . ? C21 C22 C23 119.1(3) . . ? C21 C22 H22A 120.5 . . ? C23 C22 H22A 120.5 . . ? C24 C23 C22 121.0(3) . . ? C24 C23 H23A 119.5 . . ? C22 C23 H23A 119.5 . . ? C23 C24 C24A 120.7(3) . . ? C23 C24 H24A 119.6 . . ? C24A C24 H24A 119.6 . . ? C24 C24A N25 120.3(2) . . ? C24 C24A C21A 119.2(3) . . ? N25 C24A C21A 120.5(3) . . ? C25A N25 C24A 119.2(2) . . ? C25A N25 C25 118.1(2) . . ? C24A N25 C25 120.1(2) . . ? N25 C25 H25A 109.5 . . ? N25 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? N25 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? N26 C25A N25 124.9(2) . . ? N26 C25A C30B 115.2(2) . . ? N25 C25A C30B 119.8(2) . . ? C25A N26 C26A 105.5(2) . . ? C27 C26A C30A 121.0(3) . . ? C27 C26A N26 126.3(2) . . ? C30A C26A N26 112.6(2) . . ? C26A C27 C28 118.7(3) . . ? C26A C27 H27A 120.6 . . ? C28 C27 H27A 120.6 . . ? C27 C28 C29 120.4(3) . . ? C27 C28 H28A 119.8 . . ? C29 C28 H28A 119.8 . . ? C30 C29 C28 120.7(3) . . ? C30 C29 H29A 119.6 . . ? C28 C29 H29A 119.6 . . ? C30A C30 C29 118.8(3) . . ? C30A C30 H30A 120.6 . . ? C29 C30 H30A 120.6 . . ? C30A C30B C31 120.5(2) . . ? C30A C30B C25A 99.4(2) . . ? C31 C30B C25A 111.6(2) . . ? C30A C30B C32 110.8(2) . . ? C31 C30B C32 106.9(2) . . ? C25A C30B C32 106.9(2) . . ? C30 C30A C26A 120.3(3) . . ? C30 C30A C30B 133.6(2) . . ? C26A C30A C30B 106.0(2) . . ? O31 C31 C21A 123.7(3) . . ? O31 C31 C30B 122.4(3) . . ? C21A C31 C30B 113.7(2) . . ? C33 C32 C30B 113.7(2) . . ? C33 C32 H32A 108.8 . . ? C30B C32 H32A 108.8 . . ? C33 C32 H32B 108.8 . . ? C30B C32 H32B 108.8 . . ? H32A C32 H32B 107.7 . . ? C34 C33 C32 123.7(3) . . ? C34 C33 H33A 118.1 . . ? C32 C33 H33A 118.1 . . ? C33 C34 H34A 120.0 . . ? C33 C34 H34B 120.0 . . ? H34A C34 H34B 120.0 . . ? 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 C4A C1A C1 C2 -0.6(4) . . . . ? C11 C1A C1 C2 179.5(3) . . . . ? C1A C1 C2 C3 0.7(4) . . . . ? C1 C2 C3 C4 -0.5(4) . . . . ? C2 C3 C4 C4A 0.2(4) . . . . ? C3 C4 C4A C1A 0.0(4) . . . . ? C3 C4 C4A N5 176.8(2) . . . . ? C1 C1A C4A C4 0.2(4) . . . . ? C11 C1A C4A C4 -179.8(2) . . . . ? C1 C1A C4A N5 -176.5(2) . . . . ? C11 C1A C4A N5 3.4(4) . . . . ? C4 C4A N5 C5A -179.3(2) . . . . ? C1A C4A N5 C5A -2.5(4) . . . . ? C4 C4A N5 C5 -17.5(4) . . . . ? C1A C4A N5 C5 159.3(3) . . . . ? C4A N5 C5A N6 160.8(3) . . . . ? C5 N5 C5A N6 -1.2(4) . . . . ? C4A N5 C5A C10B -21.0(3) . . . . ? C5 N5 C5A C10B 177.0(2) . . . . ? N5 C5A N6 C6A -174.1(2) . . . . ? C10B C5A N6 C6A 7.7(3) . . . . ? C5A N6 C6A C7 175.0(3) . . . . ? C5A N6 C6A C10A -0.1(3) . . . . ? C10A C6A C7 C8 1.8(4) . . . . ? N6 C6A C7 C8 -172.9(2) . . . . ? C6A C7 C8 C9 -0.1(4) . . . . ? C7 C8 C9 C10 -2.0(4) . . . . ? C8 C9 C10 C10A 2.3(4) . . . . ? N6 C5A C10B C10A -11.5(3) . . . . ? N5 C5A C10B C10A 170.2(2) . . . . ? N6 C5A C10B C11 -140.2(2) . . . . ? N5 C5A C10B C11 41.4(3) . . . . ? N6 C5A C10B C12 103.7(3) . . . . ? N5 C5A C10B C12 -74.7(3) . . . . ? C9 C10 C10A C6A -0.5(4) . . . . ? C9 C10 C10A C10B -179.3(3) . . . . ? C7 C6A C10A C10 -1.5(4) . . . . ? N6 C6A C10A C10 173.9(2) . . . . ? C7 C6A C10A C10B 177.5(2) . . . . ? N6 C6A C10A C10B -7.1(3) . . . . ? C5A C10B C10A C10 -171.0(3) . . . . ? C11 C10B C10A C10 -48.6(4) . . . . ? C12 C10B C10A C10 76.3(4) . . . . ? C5A C10B C10A C6A 10.1(3) . . . . ? C11 C10B C10A C6A 132.5(3) . . . . ? C12 C10B C10A C6A -102.6(3) . . . . ? C1 C1A C11 O11 13.8(4) . . . . ? C4A C1A C11 O11 -166.2(3) . . . . ? C1 C1A C11 C10B -161.9(2) . . . . ? C4A C1A C11 C10B 18.1(4) . . . . ? C10A C10B C11 O11 30.1(4) . . . . ? C5A C10B C11 O11 146.5(3) . . . . ? C12 C10B C11 O11 -96.8(3) . . . . ? C10A C10B C11 C1A -154.1(2) . . . . ? C5A C10B C11 C1A -37.7(3) . . . . ? C12 C10B C11 C1A 79.0(3) . . . . ? C10A C10B C12 C13 -72.2(3) . . . . ? C5A C10B C12 C13 -179.8(2) . . . . ? C11 C10B C12 C13 60.7(3) . . . . ? C10B C12 C13 C14 116.5(3) . . . . ? C24A C21A C21 C22 -0.5(4) . . . . ? C31 C21A C21 C22 -178.9(3) . . . . ? C21A C21 C22 C23 1.5(4) . . . . ? C21 C22 C23 C24 -1.5(4) . . . . ? C22 C23 C24 C24A 0.5(4) . . . . ? C23 C24 C24A N25 177.6(3) . . . . ? C23 C24 C24A C21A 0.5(4) . . . . ? C21 C21A C24A C24 -0.5(4) . . . . ? C31 C21A C24A C24 177.8(2) . . . . ? C21 C21A C24A N25 -177.6(2) . . . . ? C31 C21A C24A N25 0.6(4) . . . . ? C24 C24A N25 C25A -172.3(3) . . . . ? C21A C24A N25 C25A 4.8(4) . . . . ? C24 C24A N25 C25 -11.0(4) . . . . ? C21A C24A N25 C25 166.1(3) . . . . ? C24A N25 C25A N26 154.9(3) . . . . ? C25 N25 C25A N26 -6.7(4) . . . . ? C24A N25 C25A C30B -27.6(4) . . . . ? C25 N25 C25A C30B 170.8(2) . . . . ? N25 C25A N26 C26A -174.3(3) . . . . ? C30B C25A N26 C26A 8.1(3) . . . . ? C25A N26 C26A C27 175.4(3) . . . . ? C25A N26 C26A C30A -0.9(3) . . . . ? C30A C26A C27 C28 1.8(4) . . . . ? N26 C26A C27 C28 -174.2(3) . . . . ? C26A C27 C28 C29 -0.5(4) . . . . ? C27 C28 C29 C30 -1.5(4) . . . . ? C28 C29 C30 C30A 2.1(4) . . . . ? N26 C25A C30B C30A -11.5(3) . . . . ? N25 C25A C30B C30A 170.7(2) . . . . ? N26 C25A C30B C31 -139.7(3) . . . . ? N25 C25A C30B C31 42.6(3) . . . . ? N26 C25A C30B C32 103.7(3) . . . . ? N25 C25A C30B C32 -74.0(3) . . . . ? C29 C30 C30A C26A -0.7(4) . . . . ? C29 C30 C30A C30B -178.5(3) . . . . ? C27 C26A C30A C30 -1.2(4) . . . . ? N26 C26A C30A C30 175.3(2) . . . . ? C27 C26A C30A C30B 177.1(3) . . . . ? N26 C26A C30A C30B -6.3(3) . . . . ? C31 C30B C30A C30 -50.3(4) . . . . ? C25A C30B C30A C30 -172.3(3) . . . . ? C32 C30B C30A C30 75.5(4) . . . . ? C31 C30B C30A C26A 131.7(2) . . . . ? C25A C30B C30A C26A 9.7(3) . . . . ? C32 C30B C30A C26A -102.5(2) . . . . ? C21 C21A C31 O31 9.1(4) . . . . ? C24A C21A C31 O31 -169.1(3) . . . . ? C21 C21A C31 C30B -166.0(2) . . . . ? C24A C21A C31 C30B 15.7(4) . . . . ? C30A C30B C31 O31 34.5(4) . . . . ? C25A C30B C31 O31 150.3(3) . . . . ? C32 C30B C31 O31 -93.1(3) . . . . ? C30A C30B C31 C21A -150.3(2) . . . . ? C25A C30B C31 C21A -34.5(3) . . . . ? C32 C30B C31 C21A 82.1(3) . . . . ? C30A C30B C32 C33 -61.4(3) . . . . ? C31 C30B C32 C33 71.6(3) . . . . ? C25A C30B C32 C33 -168.8(2) . . . . ? C30B C32 C33 C34 117.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.897 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.917 _refine_diff_density_max 0.275 _refine_diff_density_min -0.327 _refine_diff_density_rms 0.070 data_14 _database_code_depnum_ccdc_archive 'CCDC 737647' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H16 N2 O' _chemical_formula_sum 'C19 H16 N2 O' _chemical_formula_weight 288.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 11.332(3) _cell_length_b 17.217(4) _cell_length_c 7.5306(19) _cell_angle_alpha 90.00 _cell_angle_beta 107.218(7) _cell_angle_gamma 90.00 _cell_volume 1403.4(6) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 4975 _cell_measurement_theta_min 1.8820 _cell_measurement_theta_max 25.3491 _exptl_crystal_description Prism _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.2000 _exptl_crystal_size_mid 0.0300 _exptl_crystal_size_min 0.0300 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.365 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9872 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type ccd _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8730 _diffrn_reflns_av_R_equivalents 0.0589 _diffrn_reflns_av_sigmaI/netI 0.0435 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 25.31 _reflns_number_total 2532 _reflns_number_gt 2172 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _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^)+(0.0892P)^2^+0.1783P] 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 2532 _refine_ls_number_parameters 201 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0593 _refine_ls_R_factor_gt 0.0510 _refine_ls_wR_factor_ref 0.1400 _refine_ls_wR_factor_gt 0.1329 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _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 C1A C 0.38806(14) 0.02376(9) 0.29086(18) 0.0196(4) Uani 1 1 d . . . C1 C 0.28301(14) 0.05258(9) 0.33010(18) 0.0216(4) Uani 1 1 d . . . H1A H 0.2728 0.1071 0.3389 0.026 Uiso 1 1 calc R . . C2 C 0.19401(14) 0.00273(10) 0.35617(19) 0.0242(4) Uani 1 1 d . . . H2A H 0.1234 0.0224 0.3846 0.029 Uiso 1 1 calc R . . C3 C 0.20971(15) -0.07712(10) 0.3400(2) 0.0260(4) Uani 1 1 d . . . H3A H 0.1483 -0.1117 0.3560 0.031 Uiso 1 1 calc R . . C4 C 0.31231(14) -0.10689(10) 0.30117(19) 0.0240(4) Uani 1 1 d . . . H4A H 0.3204 -0.1614 0.2894 0.029 Uiso 1 1 calc R . . C4A C 0.40532(14) -0.05662(9) 0.27894(18) 0.0198(4) Uani 1 1 d . . . N5 N 0.51230(11) -0.08574(7) 0.24886(15) 0.0199(3) Uani 1 1 d . . . C5 C 0.53681(15) -0.16915(9) 0.2665(2) 0.0244(4) Uani 1 1 d . . . H5A H 0.4940 -0.1949 0.1490 0.037 Uiso 1 1 calc R . . H5B H 0.5069 -0.1902 0.3662 0.037 Uiso 1 1 calc R . . H5C H 0.6259 -0.1783 0.2960 0.037 Uiso 1 1 calc R . . C5A C 0.60003(14) -0.03646(9) 0.21569(18) 0.0186(3) Uani 1 1 d . . . C6 C 0.70813(14) -0.04974(9) 0.17329(18) 0.0196(4) Uani 1 1 d . . . C6A C 0.76325(14) 0.02535(9) 0.16987(18) 0.0205(4) Uani 1 1 d . . . C7 C 0.87548(15) 0.04767(9) 0.14307(19) 0.0246(4) Uani 1 1 d . . . H7A H 0.9298 0.0098 0.1190 0.030 Uiso 1 1 calc R . . C8 C 0.90612(16) 0.12567(10) 0.1521(2) 0.0301(4) Uani 1 1 d . . . H8A H 0.9826 0.1412 0.1354 0.036 Uiso 1 1 calc R . . C9 C 0.82658(16) 0.18184(10) 0.1852(2) 0.0315(4) Uani 1 1 d . . . H9A H 0.8497 0.2350 0.1900 0.038 Uiso 1 1 calc R . . C10 C 0.71403(15) 0.16169(10) 0.2114(2) 0.0279(4) Uani 1 1 d . . . H10A H 0.6596 0.1999 0.2336 0.033 Uiso 1 1 calc R . . C10A C 0.68469(14) 0.08306(9) 0.20377(18) 0.0209(4) Uani 1 1 d . . . N11 N 0.58212(11) 0.04452(7) 0.23130(15) 0.0195(3) Uani 1 1 d . . . C12 C 0.47968(13) 0.07895(9) 0.26443(18) 0.0198(4) Uani 1 1 d . . . O12 O 0.46995(10) 0.14977(6) 0.26983(14) 0.0269(3) Uani 1 1 d . . . C13 C 0.77180(14) -0.12313(9) 0.14067(19) 0.0214(4) Uani 1 1 d . . . H13A H 0.7090 -0.1641 0.0931 0.026 Uiso 1 1 calc R . . H13B H 0.8135 -0.1131 0.0445 0.026 Uiso 1 1 calc R . . C14 C 0.86543(14) -0.15178(9) 0.31452(19) 0.0234(4) Uani 1 1 d . . . H14A H 0.9258 -0.1158 0.3815 0.028 Uiso 1 1 calc R . . C15 C 0.87048(17) -0.22312(10) 0.3817(2) 0.0298(4) Uani 1 1 d . . . H15A H 0.8118 -0.2609 0.3189 0.036 Uiso 1 1 calc R . . H15B H 0.9328 -0.2366 0.4928 0.036 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 C1A 0.0203(8) 0.0216(8) 0.0161(7) -0.0007(6) 0.0043(6) 0.0014(6) C1 0.0213(9) 0.0254(9) 0.0172(7) -0.0004(6) 0.0044(6) 0.0048(6) C2 0.0180(8) 0.0330(10) 0.0217(7) -0.0013(6) 0.0062(6) 0.0053(6) C3 0.0213(9) 0.0315(9) 0.0267(8) -0.0008(6) 0.0096(6) -0.0041(7) C4 0.0234(9) 0.0233(9) 0.0264(8) -0.0011(6) 0.0090(6) -0.0006(6) C4A 0.0178(8) 0.0238(9) 0.0178(7) 0.0003(6) 0.0054(6) 0.0016(6) N5 0.0198(7) 0.0168(7) 0.0252(6) -0.0006(5) 0.0097(5) 0.0007(5) C5 0.0239(9) 0.0162(8) 0.0359(8) 0.0004(6) 0.0133(6) 0.0004(6) C5A 0.0216(8) 0.0163(8) 0.0175(7) 0.0002(5) 0.0053(6) 0.0010(6) C6 0.0224(9) 0.0192(8) 0.0183(7) 0.0013(6) 0.0078(6) 0.0003(6) C6A 0.0207(8) 0.0231(9) 0.0180(7) 0.0022(6) 0.0062(6) 0.0000(6) C7 0.0233(9) 0.0279(9) 0.0243(7) 0.0031(6) 0.0095(6) 0.0007(7) C8 0.0246(9) 0.0317(10) 0.0355(9) 0.0062(7) 0.0109(7) -0.0043(7) C9 0.0283(10) 0.0227(9) 0.0439(9) 0.0032(7) 0.0110(7) -0.0044(7) C10 0.0273(9) 0.0212(9) 0.0348(9) 0.0015(7) 0.0087(7) -0.0002(7) C10A 0.0195(9) 0.0219(8) 0.0211(7) 0.0034(6) 0.0058(6) 0.0005(6) N11 0.0179(7) 0.0175(7) 0.0234(6) 0.0006(5) 0.0067(5) 0.0009(5) C12 0.0177(8) 0.0216(8) 0.0186(7) 0.0003(6) 0.0033(6) 0.0035(6) O12 0.0272(7) 0.0180(6) 0.0363(6) -0.0002(4) 0.0106(5) 0.0031(4) C13 0.0243(9) 0.0209(8) 0.0224(7) -0.0001(6) 0.0123(6) 0.0020(6) C14 0.0214(8) 0.0266(9) 0.0255(8) -0.0033(6) 0.0120(6) 0.0031(6) C15 0.0336(10) 0.0303(10) 0.0269(8) 0.0021(7) 0.0110(7) 0.0087(7) _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 C1A C1 1.400(2) . ? C1A C4A 1.404(2) . ? C1A C12 1.464(2) . ? C1 C2 1.382(2) . ? C1 H1A 0.9500 . ? C2 C3 1.396(2) . ? C2 H2A 0.9500 . ? C3 C4 1.379(2) . ? C3 H3A 0.9500 . ? C4 C4A 1.411(2) . ? C4 H4A 0.9500 . ? C4A N5 1.3910(19) . ? N5 C5A 1.3849(19) . ? N5 C5 1.461(2) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C5A C6 1.373(2) . ? C5A N11 1.4187(19) . ? C6 C6A 1.439(2) . ? C6 C13 1.511(2) . ? C6A C7 1.399(2) . ? C6A C10A 1.407(2) . ? C7 C8 1.384(2) . ? C7 H7A 0.9500 . ? C8 C9 1.394(2) . ? C8 H8A 0.9500 . ? C9 C10 1.391(2) . ? C9 H9A 0.9500 . ? C10 C10A 1.391(2) . ? C10 H10A 0.9500 . ? C10A N11 1.4060(18) . ? N11 C12 1.3903(18) . ? C12 O12 1.2260(19) . ? C13 C14 1.504(2) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.323(2) . ? C14 H14A 0.9500 . ? C15 H15A 0.9500 . ? C15 H15B 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 C1A C4A 120.41(14) . . ? C1 C1A C12 118.71(14) . . ? C4A C1A C12 120.88(13) . . ? C2 C1 C1A 120.80(15) . . ? C2 C1 H1A 119.6 . . ? C1A C1 H1A 119.6 . . ? C1 C2 C3 118.80(14) . . ? C1 C2 H2A 120.6 . . ? C3 C2 H2A 120.6 . . ? C4 C3 C2 121.46(15) . . ? C4 C3 H3A 119.3 . . ? C2 C3 H3A 119.3 . . ? C3 C4 C4A 120.22(15) . . ? C3 C4 H4A 119.9 . . ? C4A C4 H4A 119.9 . . ? N5 C4A C1A 120.68(13) . . ? N5 C4A C4 121.05(14) . . ? C1A C4A C4 118.27(14) . . ? C5A N5 C4A 121.03(13) . . ? C5A N5 C5 119.41(12) . . ? C4A N5 C5 119.40(12) . . ? N5 C5 H5A 109.5 . . ? N5 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N5 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C6 C5A N5 132.63(14) . . ? C6 C5A N11 110.01(13) . . ? N5 C5A N11 117.33(12) . . ? C5A C6 C6A 106.04(13) . . ? C5A C6 C13 132.75(14) . . ? C6A C6 C13 121.18(13) . . ? C7 C6A C10A 118.90(15) . . ? C7 C6A C6 131.84(15) . . ? C10A C6A C6 109.26(13) . . ? C8 C7 C6A 119.01(15) . . ? C8 C7 H7A 120.5 . . ? C6A C7 H7A 120.5 . . ? C7 C8 C9 121.06(15) . . ? C7 C8 H8A 119.5 . . ? C9 C8 H8A 119.5 . . ? C10 C9 C8 121.40(16) . . ? C10 C9 H9A 119.3 . . ? C8 C9 H9A 119.3 . . ? C9 C10 C10A 117.05(15) . . ? C9 C10 H10A 121.5 . . ? C10A C10 H10A 121.5 . . ? C10 C10A N11 130.62(14) . . ? C10 C10A C6A 122.58(14) . . ? N11 C10A C6A 106.78(13) . . ? C12 N11 C10A 126.58(13) . . ? C12 N11 C5A 125.55(12) . . ? C10A N11 C5A 107.86(12) . . ? O12 C12 N11 121.20(13) . . ? O12 C12 C1A 124.52(13) . . ? N11 C12 C1A 114.28(14) . . ? C14 C13 C6 112.37(11) . . ? C14 C13 H13A 109.1 . . ? C6 C13 H13A 109.1 . . ? C14 C13 H13B 109.1 . . ? C6 C13 H13B 109.1 . . ? H13A C13 H13B 107.9 . . ? C15 C14 C13 125.24(15) . . ? C15 C14 H14A 117.4 . . ? C13 C14 H14A 117.4 . . ? C14 C15 H15A 120.0 . . ? C14 C15 H15B 120.0 . . ? H15A C15 H15B 120.0 . . ? 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 C4A C1A C1 C2 -0.6(2) . . . . ? C12 C1A C1 C2 -179.99(12) . . . . ? C1A C1 C2 C3 -0.9(2) . . . . ? C1 C2 C3 C4 0.9(2) . . . . ? C2 C3 C4 C4A 0.7(2) . . . . ? C1 C1A C4A N5 -176.89(12) . . . . ? C12 C1A C4A N5 2.52(19) . . . . ? C1 C1A C4A C4 2.13(19) . . . . ? C12 C1A C4A C4 -178.46(12) . . . . ? C3 C4 C4A N5 176.81(12) . . . . ? C3 C4 C4A C1A -2.2(2) . . . . ? C1A C4A N5 C5A -5.02(19) . . . . ? C4 C4A N5 C5A 175.99(12) . . . . ? C1A C4A N5 C5 170.31(12) . . . . ? C4 C4A N5 C5 -8.68(19) . . . . ? C4A N5 C5A C6 -176.18(14) . . . . ? C5 N5 C5A C6 8.5(2) . . . . ? C4A N5 C5A N11 5.89(18) . . . . ? C5 N5 C5A N11 -169.44(11) . . . . ? N5 C5A C6 C6A -175.54(14) . . . . ? N11 C5A C6 C6A 2.51(15) . . . . ? N5 C5A C6 C13 2.1(3) . . . . ? N11 C5A C6 C13 -179.83(13) . . . . ? C5A C6 C6A C7 176.70(15) . . . . ? C13 C6 C6A C7 -1.3(2) . . . . ? C5A C6 C6A C10A -2.14(15) . . . . ? C13 C6 C6A C10A 179.86(12) . . . . ? C10A C6A C7 C8 0.5(2) . . . . ? C6 C6A C7 C8 -178.27(14) . . . . ? C6A C7 C8 C9 -0.7(2) . . . . ? C7 C8 C9 C10 0.4(2) . . . . ? C8 C9 C10 C10A 0.2(2) . . . . ? C9 C10 C10A N11 177.24(14) . . . . ? C9 C10 C10A C6A -0.5(2) . . . . ? C7 C6A C10A C10 0.1(2) . . . . ? C6 C6A C10A C10 179.13(13) . . . . ? C7 C6A C10A N11 -178.07(12) . . . . ? C6 C6A C10A N11 0.95(15) . . . . ? C10 C10A N11 C12 3.7(2) . . . . ? C6A C10A N11 C12 -178.27(12) . . . . ? C10 C10A N11 C5A -177.40(14) . . . . ? C6A C10A N11 C5A 0.58(14) . . . . ? C6 C5A N11 C12 176.88(12) . . . . ? N5 C5A N11 C12 -4.74(19) . . . . ? C6 C5A N11 C10A -1.99(15) . . . . ? N5 C5A N11 C10A 176.39(11) . . . . ? C10A N11 C12 O12 1.1(2) . . . . ? C5A N11 C12 O12 -177.58(12) . . . . ? C10A N11 C12 C1A -179.01(11) . . . . ? C5A N11 C12 C1A 2.33(18) . . . . ? C1 C1A C12 O12 -1.8(2) . . . . ? C4A C1A C12 O12 178.77(12) . . . . ? C1 C1A C12 N11 178.29(11) . . . . ? C4A C1A C12 N11 -1.13(18) . . . . ? C5A C6 C13 C14 -93.54(19) . . . . ? C6A C6 C13 C14 83.84(16) . . . . ? C6 C13 C14 C15 127.84(15) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.241 _refine_diff_density_min -0.324 _refine_diff_density_rms 0.054 data_18 _database_code_depnum_ccdc_archive 'CCDC 737648' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_absolute_configuration ad _chemical_formula_moiety 'C26 H21 Br N2 O' _chemical_formula_sum 'C26 H21 Br N2 O' _chemical_formula_weight 457.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Triclinic _symmetry_space_group_name_H-M P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 8.7486(17) _cell_length_b 9.3067(19) _cell_length_c 13.714(3) _cell_angle_alpha 101.33(3) _cell_angle_beta 99.93(3) _cell_angle_gamma 90.56(3) _cell_volume 1077.4(4) _cell_formula_units_Z 2 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 3353 _cell_measurement_theta_min 2.2340 _cell_measurement_theta_max 28.5009 _exptl_crystal_description Prism _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.1000 _exptl_crystal_size_mid 0.1000 _exptl_crystal_size_min 0.0800 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.410 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 468 _exptl_absorpt_coefficient_mu 1.928 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6056 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type CCD _diffrn_measurement_method dtprofit.ref _diffrn_detector_area_resol_mean 0.83 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6436 _diffrn_reflns_av_R_equivalents 0.0640 _diffrn_reflns_av_sigmaI/netI 0.1170 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 25.28 _reflns_number_total 4997 _reflns_number_gt 4036 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _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^)+(0.0537P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.022(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.005(14) _refine_ls_number_reflns 4997 _refine_ls_number_parameters 545 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0775 _refine_ls_R_factor_gt 0.0621 _refine_ls_wR_factor_ref 0.1376 _refine_ls_wR_factor_gt 0.1269 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.002 _refine_ls_shift/su_max 0.016 _refine_ls_shift/su_mean 0.001 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 -0.03010(10) -0.23210(10) -0.75041(7) 0.0443(3) Uani 1 1 d . . . C1 C -0.2069(13) -0.2469(11) -0.6876(8) 0.034(2) Uani 1 1 d . . . C2 C -0.3414(13) -0.3177(10) -0.7463(7) 0.040(3) Uani 1 1 d . . . H2A H -0.3409 -0.3624 -0.8147 0.047 Uiso 1 1 calc R . . C3 C -0.4773(11) -0.3248(11) -0.7073(8) 0.039(2) Uani 1 1 d . . . H3A H -0.5682 -0.3734 -0.7494 0.047 Uiso 1 1 calc R . . C4 C -0.4809(11) -0.2605(11) -0.6063(7) 0.033(2) Uani 1 1 d . . . H4A H -0.5725 -0.2643 -0.5781 0.040 Uiso 1 1 calc R . . C4A C -0.3391(12) -0.1888(10) -0.5476(8) 0.024(2) Uani 1 1 d . . . N5 N -0.3267(8) -0.1194(9) -0.4455(5) 0.0284(17) Uani 1 1 d . . . C5A C -0.1822(10) -0.0689(9) -0.4195(6) 0.0249(19) Uani 1 1 d . . . N6 N -0.1157(8) 0.0021(8) -0.3233(5) 0.0233(16) Uani 1 1 d . . . C6A C 0.0459(10) 0.0008(9) -0.2946(6) 0.0241(19) Uani 1 1 d . . . C7 C 0.1205(10) 0.0710(10) -0.1959(6) 0.028(2) Uani 1 1 d . . . H7A H 0.0616 0.1263 -0.1508 0.033 Uiso 1 1 calc R . . C8 C 0.2744(12) 0.0595(11) -0.1659(8) 0.037(2) Uani 1 1 d . . . H8A H 0.3207 0.1028 -0.0985 0.045 Uiso 1 1 calc R . . C9 C 0.3677(11) -0.0143(11) -0.2311(8) 0.036(2) Uani 1 1 d . . . H9A H 0.4762 -0.0191 -0.2086 0.043 Uiso 1 1 calc R . . C10 C 0.3011(10) -0.0794(10) -0.3278(7) 0.027(2) Uani 1 1 d . . . H10A H 0.3640 -0.1294 -0.3725 0.033 Uiso 1 1 calc R . . C10A C 0.1416(10) -0.0732(10) -0.3614(7) 0.028(2) Uani 1 1 d . . . C11 C 0.0714(12) -0.1400(10) -0.4670(8) 0.027(2) Uani 1 1 d . . . O11 O 0.1426(8) -0.2247(7) -0.5233(5) 0.0307(15) Uani 1 1 d . . . C11A C -0.0857(10) -0.0893(10) -0.5043(6) 0.028(2) Uani 1 1 d . . . C11B C -0.2052(12) -0.1856(10) -0.5854(7) 0.025(2) Uani 1 1 d . . . C12 C -0.0542(10) 0.0661(10) -0.5300(7) 0.029(2) Uani 1 1 d . . . H12A H -0.0162 0.1365 -0.4659 0.034 Uiso 1 1 calc R . . H12B H 0.0298 0.0576 -0.5705 0.034 Uiso 1 1 calc R . . C13 C -0.1900(12) 0.1270(10) -0.5857(6) 0.030(2) Uani 1 1 d . . . H13A H -0.2828 0.1361 -0.5582 0.036 Uiso 1 1 calc R . . C14 C -0.1882(12) 0.1691(11) -0.6714(7) 0.040(2) Uani 1 1 d . . . H14A H -0.0957 0.1542 -0.6988 0.048 Uiso 1 1 calc R . . C15 C -0.3170(15) 0.2381(12) -0.7302(9) 0.050(3) Uani 1 1 d . . . H15A H -0.4119 0.2311 -0.7021 0.075 Uiso 1 1 calc R . . H15B H -0.3351 0.1868 -0.8011 0.075 Uiso 1 1 calc R . . H15C H -0.2883 0.3415 -0.7259 0.075 Uiso 1 1 calc R . . C16 C -0.2149(11) 0.0495(10) -0.2476(7) 0.030(2) Uani 1 1 d . . . H16A H -0.3227 0.0552 -0.2829 0.036 Uiso 1 1 calc R . . H16B H -0.1790 0.1493 -0.2096 0.036 Uiso 1 1 calc R . . C17 C -0.2153(12) -0.0512(11) -0.1733(7) 0.027(2) Uani 1 1 d . . . C18 C -0.1787(11) 0.0082(12) -0.0687(7) 0.036(2) Uani 1 1 d . . . H18A H -0.1494 0.1095 -0.0466 0.043 Uiso 1 1 calc R . . C19 C -0.1845(13) -0.0777(14) 0.0028(9) 0.042(3) Uani 1 1 d . . . H19A H -0.1585 -0.0365 0.0729 0.051 Uiso 1 1 calc R . . C20 C -0.2299(11) -0.2283(12) -0.0312(8) 0.039(2) Uani 1 1 d . . . H20A H -0.2345 -0.2889 0.0166 0.047 Uiso 1 1 calc R . . C21 C -0.2675(11) -0.2871(11) -0.1330(7) 0.034(2) Uani 1 1 d . . . H21A H -0.2998 -0.3877 -0.1559 0.041 Uiso 1 1 calc R . . C22 C -0.2574(10) -0.1968(11) -0.2028(7) 0.028(2) Uani 1 1 d . . . H22A H -0.2807 -0.2386 -0.2729 0.033 Uiso 1 1 calc R . . Br31 Br 0.13086(9) -0.53180(9) 0.09018(7) 0.0415(3) Uani 1 1 d . . . C31 C 0.2971(11) -0.5779(11) 0.0202(7) 0.028(2) Uani 1 1 d . . . C32 C 0.4335(11) -0.6286(10) 0.0731(7) 0.032(2) Uani 1 1 d . . . H32A H 0.4350 -0.6450 0.1395 0.038 Uiso 1 1 calc R . . C33 C 0.5628(12) -0.6539(10) 0.0297(7) 0.036(2) Uani 1 1 d . . . H33A H 0.6520 -0.6887 0.0666 0.044 Uiso 1 1 calc R . . C34 C 0.5677(11) -0.6303(11) -0.0674(7) 0.032(2) Uani 1 1 d . . . H34A H 0.6583 -0.6469 -0.0969 0.039 Uiso 1 1 calc R . . C34A C 0.4350(13) -0.5820(11) -0.1179(8) 0.026(2) Uani 1 1 d . . . N35 N 0.4176(9) -0.5555(8) -0.2204(5) 0.0278(17) Uani 1 1 d . . . C35A C 0.2739(10) -0.5166(10) -0.2388(7) 0.030(2) Uani 1 1 d . . . N36 N 0.2070(8) -0.4920(9) -0.3325(5) 0.0289(17) Uani 1 1 d . . . C36A C 0.0429(10) -0.5078(9) -0.3614(6) 0.026(2) Uani 1 1 d . . . C37 C -0.0281(10) -0.4865(10) -0.4551(7) 0.030(2) Uani 1 1 d . . . H37A H 0.0316 -0.4539 -0.4989 0.036 Uiso 1 1 calc R . . C38 C -0.1881(11) -0.5131(10) -0.4851(8) 0.036(2) Uani 1 1 d . . . H38A H -0.2362 -0.4993 -0.5500 0.044 Uiso 1 1 calc R . . C39 C -0.2781(11) -0.5590(10) -0.4230(7) 0.035(2) Uani 1 1 d . . . H39A H -0.3868 -0.5775 -0.4452 0.042 Uiso 1 1 calc R . . C40 C -0.2090(10) -0.5782(11) -0.3277(7) 0.032(2) Uani 1 1 d . . . H40A H -0.2700 -0.6087 -0.2838 0.038 Uiso 1 1 calc R . . C40A C -0.0460(10) -0.5517(10) -0.2968(7) 0.029(2) Uani 1 1 d . . . C41 C 0.0222(10) -0.5688(9) -0.1920(7) 0.024(2) Uani 1 1 d . . . O41 O -0.0526(8) -0.6259(7) -0.1373(5) 0.0337(16) Uani 1 1 d . . . C41A C 0.1811(10) -0.4999(10) -0.1559(6) 0.028(2) Uani 1 1 d . . . C41B C 0.2966(12) -0.5575(11) -0.0781(8) 0.029(2) Uani 1 1 d . . . C42 C 0.1514(11) -0.3320(9) -0.1171(7) 0.032(2) Uani 1 1 d . . . H42A H 0.1112 -0.2883 -0.1761 0.038 Uiso 1 1 calc R . . H42B H 0.0700 -0.3258 -0.0746 0.038 Uiso 1 1 calc R . . C43 C 0.2947(11) -0.2416(10) -0.0563(6) 0.031(2) Uani 1 1 d . . . H43A H 0.3872 -0.2424 -0.0839 0.038 Uiso 1 1 calc R . . C44 C 0.2918(12) -0.1620(10) 0.0345(7) 0.036(2) Uani 1 1 d . . . H44A H 0.2011 -0.1697 0.0629 0.043 Uiso 1 1 calc R . . C45 C 0.4227(13) -0.0605(11) 0.0950(8) 0.038(3) Uani 1 1 d . . . H45A H 0.5076 -0.0624 0.0566 0.057 Uiso 1 1 calc R . . H45B H 0.4601 -0.0920 0.1587 0.057 Uiso 1 1 calc R . . H45C H 0.3864 0.0395 0.1093 0.057 Uiso 1 1 calc R . . C46 C 0.3036(11) -0.4876(11) -0.4110(7) 0.033(2) Uani 1 1 d . . . H46A H 0.2676 -0.4086 -0.4472 0.040 Uiso 1 1 calc R . . H46B H 0.4123 -0.4614 -0.3770 0.040 Uiso 1 1 calc R . . C47 C 0.3010(11) -0.6262(11) -0.4863(7) 0.030(2) Uani 1 1 d . . . C48 C 0.2653(11) -0.6258(13) -0.5880(7) 0.040(2) Uani 1 1 d . . . H48A H 0.2355 -0.5378 -0.6098 0.048 Uiso 1 1 calc R . . C49 C 0.2727(15) -0.7544(14) -0.6596(8) 0.047(3) Uani 1 1 d . . . H49A H 0.2471 -0.7511 -0.7293 0.056 Uiso 1 1 calc R . . C50 C 0.3160(12) -0.8871(12) -0.6327(8) 0.043(3) Uani 1 1 d . . . H50A H 0.3156 -0.9749 -0.6817 0.052 Uiso 1 1 calc R . . C51 C 0.3604(11) -0.8829(12) -0.5281(8) 0.040(2) Uani 1 1 d . . . H51A H 0.3989 -0.9685 -0.5062 0.048 Uiso 1 1 calc R . . C52 C 0.3496(11) -0.7590(11) -0.4572(8) 0.033(2) Uani 1 1 d . . . H52A H 0.3751 -0.7621 -0.3875 0.039 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 Br1 0.0417(7) 0.0589(8) 0.0308(6) 0.0046(5) 0.0076(5) 0.0041(5) C1 0.033(6) 0.027(6) 0.039(5) 0.003(4) 0.004(5) 0.001(4) C2 0.058(7) 0.024(5) 0.033(5) 0.003(4) 0.002(5) 0.008(5) C3 0.030(5) 0.032(6) 0.053(6) -0.004(5) 0.010(5) -0.006(4) C4 0.028(5) 0.032(5) 0.034(5) 0.005(4) -0.006(4) 0.001(4) C4A 0.022(5) 0.013(5) 0.029(5) -0.009(4) 0.003(5) -0.002(4) N5 0.016(4) 0.036(5) 0.030(4) 0.003(4) 0.001(3) -0.005(3) C5A 0.028(5) 0.019(5) 0.029(4) 0.012(4) -0.002(4) 0.005(4) N6 0.017(4) 0.028(4) 0.024(4) 0.003(3) 0.005(3) -0.001(3) C6A 0.022(4) 0.018(5) 0.032(5) 0.005(4) 0.005(4) 0.001(4) C7 0.018(4) 0.034(5) 0.030(5) 0.007(4) 0.004(4) 0.005(4) C8 0.035(6) 0.032(6) 0.043(5) 0.018(4) -0.009(5) -0.006(4) C9 0.021(5) 0.042(6) 0.053(6) 0.021(5) 0.019(5) 0.002(4) C10 0.017(4) 0.032(5) 0.035(5) 0.007(4) 0.010(4) 0.006(4) C10A 0.025(5) 0.025(5) 0.035(5) 0.010(4) 0.000(4) 0.002(4) C11 0.030(5) 0.016(5) 0.037(5) 0.010(4) 0.009(5) -0.003(4) O11 0.029(4) 0.034(4) 0.033(3) 0.015(3) 0.006(3) 0.006(3) C11A 0.026(5) 0.032(5) 0.024(4) 0.002(4) 0.003(4) 0.006(4) C11B 0.027(6) 0.021(5) 0.026(5) 0.006(4) 0.001(5) 0.005(4) C12 0.024(5) 0.028(5) 0.035(5) 0.008(4) 0.006(4) 0.003(4) C13 0.040(6) 0.025(5) 0.025(5) 0.003(4) 0.011(4) 0.006(4) C14 0.041(6) 0.036(6) 0.039(5) 0.007(5) -0.001(5) 0.002(5) C15 0.064(8) 0.027(6) 0.052(7) 0.015(5) -0.011(6) -0.007(6) C16 0.023(5) 0.028(5) 0.035(5) -0.001(4) 0.006(4) 0.005(4) C17 0.023(5) 0.034(6) 0.022(5) 0.006(4) 0.001(4) -0.001(4) C18 0.032(5) 0.047(7) 0.025(5) 0.003(4) 0.001(4) -0.004(5) C19 0.031(6) 0.065(8) 0.031(6) 0.015(6) -0.004(5) -0.002(6) C20 0.032(5) 0.051(7) 0.044(6) 0.023(5) 0.018(5) 0.018(5) C21 0.026(5) 0.039(6) 0.040(5) 0.010(4) 0.008(4) -0.003(4) C22 0.020(5) 0.040(6) 0.029(5) 0.010(4) 0.018(4) 0.014(4) Br31 0.0343(6) 0.0525(7) 0.0368(6) 0.0041(5) 0.0091(5) 0.0037(5) C31 0.018(5) 0.036(6) 0.029(5) 0.009(4) 0.005(4) 0.004(4) C32 0.033(6) 0.035(6) 0.031(5) 0.012(4) 0.008(5) 0.006(4) C33 0.032(5) 0.032(6) 0.040(5) 0.010(4) -0.011(5) 0.004(4) C34 0.022(5) 0.041(6) 0.030(5) 0.003(4) -0.002(4) 0.001(4) C34A 0.028(6) 0.022(5) 0.031(6) 0.012(4) 0.006(5) 0.004(4) N35 0.027(4) 0.027(4) 0.029(4) 0.006(3) 0.004(4) -0.002(3) C35A 0.024(5) 0.032(5) 0.032(5) 0.005(4) 0.002(4) 0.003(4) N36 0.018(4) 0.043(5) 0.026(4) 0.011(3) 0.001(3) -0.001(3) C36A 0.018(4) 0.023(5) 0.034(5) 0.005(4) -0.008(4) -0.003(4) C37 0.020(5) 0.030(5) 0.038(5) 0.009(4) -0.003(4) 0.002(4) C38 0.026(5) 0.024(5) 0.054(6) 0.007(4) -0.005(5) 0.005(4) C39 0.020(5) 0.031(5) 0.048(6) -0.001(5) -0.005(5) 0.001(4) C40 0.023(5) 0.039(6) 0.034(5) 0.002(4) 0.009(4) 0.007(4) C40A 0.020(5) 0.023(5) 0.041(5) 0.003(4) 0.002(4) 0.001(4) C41 0.016(4) 0.018(5) 0.032(5) -0.008(4) 0.004(4) 0.003(4) O41 0.031(4) 0.029(4) 0.044(4) 0.014(3) 0.007(3) -0.004(3) C41A 0.023(5) 0.027(5) 0.030(4) 0.008(4) -0.007(4) -0.005(4) C41B 0.017(5) 0.027(5) 0.038(6) 0.003(4) -0.002(5) 0.001(4) C42 0.028(5) 0.022(5) 0.039(5) -0.002(4) 0.001(4) -0.006(4) C43 0.031(5) 0.036(6) 0.027(5) 0.007(4) 0.003(4) -0.004(4) C44 0.036(5) 0.025(5) 0.040(5) 0.008(4) -0.012(5) -0.014(4) C45 0.043(6) 0.031(6) 0.035(6) -0.003(5) 0.004(5) 0.001(5) C46 0.024(5) 0.039(6) 0.038(5) 0.015(4) 0.000(5) 0.005(4) C47 0.018(5) 0.036(6) 0.034(5) 0.008(5) 0.000(4) -0.002(4) C48 0.026(5) 0.055(7) 0.036(5) 0.009(5) 0.001(5) 0.002(5) C49 0.054(8) 0.067(9) 0.022(5) 0.011(5) 0.013(6) 0.002(6) C50 0.037(6) 0.038(6) 0.053(6) 0.008(5) 0.005(5) -0.003(5) C51 0.031(5) 0.045(7) 0.047(6) 0.009(5) 0.014(5) 0.001(5) C52 0.020(5) 0.031(6) 0.048(6) 0.011(5) 0.007(5) -0.004(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 Br1 C1 1.911(11) . ? C1 C2 1.384(14) . ? C1 C11B 1.403(14) . ? C2 C3 1.391(14) . ? C2 H2A 0.9500 . ? C3 C4 1.404(13) . ? C3 H3A 0.9500 . ? C4 C4A 1.435(13) . ? C4 H4A 0.9500 . ? C4A C11B 1.363(15) . ? C4A N5 1.407(12) . ? N5 C5A 1.309(11) . ? C5A N6 1.379(10) . ? C5A C11A 1.535(13) . ? N6 C6A 1.401(11) . ? N6 C16 1.471(12) . ? C6A C7 1.423(12) . ? C6A C10A 1.429(12) . ? C7 C8 1.350(13) . ? C7 H7A 0.9500 . ? C8 C9 1.400(15) . ? C8 H8A 0.9500 . ? C9 C10 1.370(13) . ? C9 H9A 0.9500 . ? C10 C10A 1.397(12) . ? C10 H10A 0.9500 . ? C10A C11 1.480(13) . ? C11 O11 1.242(11) . ? C11 C11A 1.496(13) . ? C11A C11B 1.524(13) . ? C11A C12 1.586(12) . ? C12 C13 1.480(12) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.312(13) . ? C13 H13A 0.9500 . ? C14 C15 1.495(15) . ? C14 H14A 0.9500 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.514(13) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C22 1.363(14) . ? C17 C18 1.412(13) . ? C18 C19 1.387(15) . ? C18 H18A 0.9500 . ? C19 C20 1.417(16) . ? C19 H19A 0.9500 . ? C20 C21 1.377(13) . ? C20 H20A 0.9500 . ? C21 C22 1.405(13) . ? C21 H21A 0.9500 . ? C22 H22A 0.9500 . ? Br31 C31 1.884(9) . ? C31 C41B 1.397(14) . ? C31 C32 1.422(13) . ? C32 C33 1.368(14) . ? C32 H32A 0.9500 . ? C33 C34 1.399(13) . ? C33 H33A 0.9500 . ? C34 C34A 1.373(14) . ? C34 H34A 0.9500 . ? C34A C41B 1.414(15) . ? C34A N35 1.457(13) . ? N35 C35A 1.308(11) . ? C35A N36 1.380(11) . ? C35A C41A 1.492(13) . ? N36 C36A 1.420(11) . ? N36 C46 1.484(12) . ? C36A C37 1.380(12) . ? C36A C40A 1.390(13) . ? C37 C38 1.394(12) . ? C37 H37A 0.9500 . ? C38 C39 1.377(14) . ? C38 H38A 0.9500 . ? C39 C40 1.387(13) . ? C39 H39A 0.9500 . ? C40 C40A 1.421(12) . ? C40 H40A 0.9500 . ? C40A C41 1.497(13) . ? C41 O41 1.262(11) . ? C41 C41A 1.487(12) . ? C41A C41B 1.521(13) . ? C41A C42 1.588(12) . ? C42 C43 1.523(12) . ? C42 H42A 0.9900 . ? C42 H42B 0.9900 . ? C43 C44 1.322(13) . ? C43 H43A 0.9500 . ? C44 C45 1.496(13) . ? C44 H44A 0.9500 . ? C45 H45A 0.9800 . ? C45 H45B 0.9800 . ? C45 H45C 0.9800 . ? C46 C47 1.484(14) . ? C46 H46A 0.9900 . ? C46 H46B 0.9900 . ? C47 C48 1.377(13) . ? C47 C52 1.419(14) . ? C48 C49 1.401(16) . ? C48 H48A 0.9500 . ? C49 C50 1.394(16) . ? C49 H49A 0.9500 . ? C50 C51 1.413(14) . ? C50 H50A 0.9500 . ? C51 C52 1.370(14) . ? C51 H51A 0.9500 . ? C52 H52A 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 C2 C1 C11B 119.5(10) . . ? C2 C1 Br1 118.4(8) . . ? C11B C1 Br1 122.1(8) . . ? C1 C2 C3 121.5(9) . . ? C1 C2 H2A 119.2 . . ? C3 C2 H2A 119.2 . . ? C2 C3 C4 120.4(9) . . ? C2 C3 H3A 119.8 . . ? C4 C3 H3A 119.8 . . ? C3 C4 C4A 116.5(9) . . ? C3 C4 H4A 121.8 . . ? C4A C4 H4A 121.8 . . ? C11B C4A N5 114.7(8) . . ? C11B C4A C4 122.8(9) . . ? N5 C4A C4 122.4(9) . . ? C5A N5 C4A 104.0(7) . . ? N5 C5A N6 124.2(8) . . ? N5 C5A C11A 116.1(7) . . ? N6 C5A C11A 119.7(8) . . ? C5A N6 C6A 118.3(7) . . ? C5A N6 C16 119.7(7) . . ? C6A N6 C16 120.8(7) . . ? N6 C6A C7 120.6(7) . . ? N6 C6A C10A 122.0(7) . . ? C7 C6A C10A 117.4(8) . . ? C8 C7 C6A 120.4(9) . . ? C8 C7 H7A 119.8 . . ? C6A C7 H7A 119.8 . . ? C7 C8 C9 122.0(9) . . ? C7 C8 H8A 119.0 . . ? C9 C8 H8A 119.0 . . ? C10 C9 C8 119.3(9) . . ? C10 C9 H9A 120.3 . . ? C8 C9 H9A 120.3 . . ? C9 C10 C10A 120.6(9) . . ? C9 C10 H10A 119.7 . . ? C10A C10 H10A 119.7 . . ? C10 C10A C6A 120.1(8) . . ? C10 C10A C11 120.3(8) . . ? C6A C10A C11 119.6(8) . . ? O11 C11 C10A 122.2(9) . . ? O11 C11 C11A 121.9(9) . . ? C10A C11 C11A 115.7(8) . . ? C11 C11A C11B 122.7(8) . . ? C11 C11A C5A 109.7(7) . . ? C11B C11A C5A 97.2(7) . . ? C11 C11A C12 105.2(7) . . ? C11B C11A C12 112.7(7) . . ? C5A C11A C12 108.7(7) . . ? C4A C11B C1 119.1(9) . . ? C4A C11B C11A 107.3(8) . . ? C1 C11B C11A 132.8(9) . . ? C13 C12 C11A 115.2(7) . . ? C13 C12 H12A 108.5 . . ? C11A C12 H12A 108.5 . . ? C13 C12 H12B 108.5 . . ? C11A C12 H12B 108.5 . . ? H12A C12 H12B 107.5 . . ? C14 C13 C12 123.0(9) . . ? C14 C13 H13A 118.5 . . ? C12 C13 H13A 118.5 . . ? C13 C14 C15 126.6(11) . . ? C13 C14 H14A 116.7 . . ? C15 C14 H14A 116.7 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N6 C16 C17 113.7(8) . . ? N6 C16 H16A 108.8 . . ? C17 C16 H16A 108.8 . . ? N6 C16 H16B 108.8 . . ? C17 C16 H16B 108.8 . . ? H16A C16 H16B 107.7 . . ? C22 C17 C18 117.9(9) . . ? C22 C17 C16 122.8(8) . . ? C18 C17 C16 119.2(9) . . ? C19 C18 C17 121.6(10) . . ? C19 C18 H18A 119.2 . . ? C17 C18 H18A 119.2 . . ? C18 C19 C20 118.6(10) . . ? C18 C19 H19A 120.7 . . ? C20 C19 H19A 120.7 . . ? C21 C20 C19 120.3(9) . . ? C21 C20 H20A 119.9 . . ? C19 C20 H20A 119.9 . . ? C20 C21 C22 119.2(10) . . ? C20 C21 H21A 120.4 . . ? C22 C21 H21A 120.4 . . ? C17 C22 C21 122.3(9) . . ? C17 C22 H22A 118.9 . . ? C21 C22 H22A 118.9 . . ? C41B C31 C32 118.5(9) . . ? C41B C31 Br31 123.8(7) . . ? C32 C31 Br31 117.6(7) . . ? C33 C32 C31 120.8(8) . . ? C33 C32 H32A 119.6 . . ? C31 C32 H32A 119.6 . . ? C32 C33 C34 122.1(9) . . ? C32 C33 H33A 119.0 . . ? C34 C33 H33A 119.0 . . ? C34A C34 C33 116.5(9) . . ? C34A C34 H34A 121.7 . . ? C33 C34 H34A 121.7 . . ? C34 C34A C41B 124.0(9) . . ? C34 C34A N35 124.1(9) . . ? C41B C34A N35 111.9(9) . . ? C35A N35 C34A 103.3(8) . . ? N35 C35A N36 121.6(8) . . ? N35 C35A C41A 118.5(8) . . ? N36 C35A C41A 119.8(8) . . ? C35A N36 C36A 118.6(7) . . ? C35A N36 C46 120.3(7) . . ? C36A N36 C46 119.2(7) . . ? C37 C36A C40A 119.8(8) . . ? C37 C36A N36 120.4(8) . . ? C40A C36A N36 119.8(7) . . ? C36A C37 C38 119.6(9) . . ? C36A C37 H37A 120.2 . . ? C38 C37 H37A 120.2 . . ? C39 C38 C37 121.6(9) . . ? C39 C38 H38A 119.2 . . ? C37 C38 H38A 119.2 . . ? C38 C39 C40 119.6(9) . . ? C38 C39 H39A 120.2 . . ? C40 C39 H39A 120.2 . . ? C39 C40 C40A 119.1(9) . . ? C39 C40 H40A 120.4 . . ? C40A C40 H40A 120.4 . . ? C36A C40A C40 120.3(8) . . ? C36A C40A C41 122.5(8) . . ? C40 C40A C41 117.1(8) . . ? O41 C41 C41A 123.4(9) . . ? O41 C41 C40A 123.2(8) . . ? C41A C41 C40A 113.2(8) . . ? C41 C41A C35A 111.8(7) . . ? C41 C41A C41B 121.1(8) . . ? C35A C41A C41B 98.7(7) . . ? C41 C41A C42 103.7(7) . . ? C35A C41A C42 110.6(7) . . ? C41B C41A C42 111.0(7) . . ? C31 C41B C34A 118.0(9) . . ? C31 C41B C41A 134.6(9) . . ? C34A C41B C41A 107.1(8) . . ? C43 C42 C41A 114.3(7) . . ? C43 C42 H42A 108.7 . . ? C41A C42 H42A 108.7 . . ? C43 C42 H42B 108.7 . . ? C41A C42 H42B 108.7 . . ? H42A C42 H42B 107.6 . . ? C44 C43 C42 120.7(9) . . ? C44 C43 H43A 119.7 . . ? C42 C43 H43A 119.7 . . ? C43 C44 C45 123.8(9) . . ? C43 C44 H44A 118.1 . . ? C45 C44 H44A 118.1 . . ? C44 C45 H45A 109.5 . . ? C44 C45 H45B 109.5 . . ? H45A C45 H45B 109.5 . . ? C44 C45 H45C 109.5 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? C47 C46 N36 115.1(8) . . ? C47 C46 H46A 108.5 . . ? N36 C46 H46A 108.5 . . ? C47 C46 H46B 108.5 . . ? N36 C46 H46B 108.5 . . ? H46A C46 H46B 107.5 . . ? C48 C47 C52 117.9(10) . . ? C48 C47 C46 120.2(10) . . ? C52 C47 C46 121.7(9) . . ? C47 C48 C49 120.4(10) . . ? C47 C48 H48A 119.8 . . ? C49 C48 H48A 119.8 . . ? C50 C49 C48 122.7(10) . . ? C50 C49 H49A 118.7 . . ? C48 C49 H49A 118.7 . . ? C49 C50 C51 115.9(10) . . ? C49 C50 H50A 122.1 . . ? C51 C50 H50A 122.1 . . ? C52 C51 C50 121.9(10) . . ? C52 C51 H51A 119.0 . . ? C50 C51 H51A 119.0 . . ? C51 C52 C47 121.0(10) . . ? C51 C52 H52A 119.5 . . ? C47 C52 H52A 119.5 . . ? 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 C11B C1 C2 C3 2.5(15) . . . . ? Br1 C1 C2 C3 -176.0(8) . . . . ? C1 C2 C3 C4 -0.5(15) . . . . ? C2 C3 C4 C4A 0.1(14) . . . . ? C3 C4 C4A C11B -1.9(15) . . . . ? C3 C4 C4A N5 179.7(9) . . . . ? C11B C4A N5 C5A 1.3(11) . . . . ? C4 C4A N5 C5A 179.8(9) . . . . ? C4A N5 C5A N6 -176.9(8) . . . . ? C4A N5 C5A C11A 4.5(10) . . . . ? N5 C5A N6 C6A 155.8(8) . . . . ? C11A C5A N6 C6A -25.7(11) . . . . ? N5 C5A N6 C16 -11.4(12) . . . . ? C11A C5A N6 C16 167.1(8) . . . . ? C5A N6 C6A C7 -179.3(8) . . . . ? C16 N6 C6A C7 -12.2(12) . . . . ? C5A N6 C6A C10A -0.8(12) . . . . ? C16 N6 C6A C10A 166.3(8) . . . . ? N6 C6A C7 C8 174.7(8) . . . . ? C10A C6A C7 C8 -3.8(13) . . . . ? C6A C7 C8 C9 3.4(14) . . . . ? C7 C8 C9 C10 -1.3(14) . . . . ? C8 C9 C10 C10A -0.2(14) . . . . ? C9 C10 C10A C6A -0.5(13) . . . . ? C9 C10 C10A C11 178.1(8) . . . . ? N6 C6A C10A C10 -176.1(8) . . . . ? C7 C6A C10A C10 2.4(12) . . . . ? N6 C6A C10A C11 5.3(12) . . . . ? C7 C6A C10A C11 -176.2(8) . . . . ? C10 C10A C11 O11 13.0(13) . . . . ? C6A C10A C11 O11 -168.4(8) . . . . ? C10 C10A C11 C11A -162.0(8) . . . . ? C6A C10A C11 C11A 16.6(12) . . . . ? O11 C11 C11A C11B 33.7(13) . . . . ? C10A C11 C11A C11B -151.3(8) . . . . ? O11 C11 C11A C5A 146.5(8) . . . . ? C10A C11 C11A C5A -38.5(10) . . . . ? O11 C11 C11A C12 -96.8(9) . . . . ? C10A C11 C11A C12 78.2(9) . . . . ? N5 C5A C11A C11 -136.3(8) . . . . ? N6 C5A C11A C11 45.1(10) . . . . ? N5 C5A C11A C11B -7.7(10) . . . . ? N6 C5A C11A C11B 173.7(7) . . . . ? N5 C5A C11A C12 109.2(8) . . . . ? N6 C5A C11A C12 -69.4(9) . . . . ? N5 C4A C11B C1 -177.6(9) . . . . ? C4 C4A C11B C1 3.9(15) . . . . ? N5 C4A C11B C11A -6.3(11) . . . . ? C4 C4A C11B C11A 175.2(9) . . . . ? C2 C1 C11B C4A -4.2(15) . . . . ? Br1 C1 C11B C4A 174.3(8) . . . . ? C2 C1 C11B C11A -172.8(9) . . . . ? Br1 C1 C11B C11A 5.6(16) . . . . ? C11 C11A C11B C4A 126.6(10) . . . . ? C5A C11A C11B C4A 7.6(9) . . . . ? C12 C11A C11B C4A -106.2(9) . . . . ? C11 C11A C11B C1 -63.8(15) . . . . ? C5A C11A C11B C1 177.2(11) . . . . ? C12 C11A C11B C1 63.5(13) . . . . ? C11 C11A C12 C13 169.5(8) . . . . ? C11B C11A C12 C13 33.4(10) . . . . ? C5A C11A C12 C13 -73.1(9) . . . . ? C11A C12 C13 C14 -125.5(10) . . . . ? C12 C13 C14 C15 -177.0(9) . . . . ? C5A N6 C16 C17 101.1(9) . . . . ? C6A N6 C16 C17 -65.8(10) . . . . ? N6 C16 C17 C22 -57.6(12) . . . . ? N6 C16 C17 C18 125.8(10) . . . . ? C22 C17 C18 C19 0.2(15) . . . . ? C16 C17 C18 C19 176.9(10) . . . . ? C17 C18 C19 C20 -0.7(16) . . . . ? C18 C19 C20 C21 0.0(15) . . . . ? C19 C20 C21 C22 1.2(14) . . . . ? C18 C17 C22 C21 1.0(14) . . . . ? C16 C17 C22 C21 -175.6(9) . . . . ? C20 C21 C22 C17 -1.7(14) . . . . ? C41B C31 C32 C33 1.4(14) . . . . ? Br31 C31 C32 C33 -175.2(7) . . . . ? C31 C32 C33 C34 0.6(15) . . . . ? C32 C33 C34 C34A -0.9(14) . . . . ? C33 C34 C34A C41B -0.9(15) . . . . ? C33 C34 C34A N35 -178.3(9) . . . . ? C34 C34A N35 C35A 177.8(10) . . . . ? C41B C34A N35 C35A 0.2(10) . . . . ? C34A N35 C35A N36 -175.1(8) . . . . ? C34A N35 C35A C41A 4.5(11) . . . . ? N35 C35A N36 C36A 155.3(8) . . . . ? C41A C35A N36 C36A -24.3(12) . . . . ? N35 C35A N36 C46 -9.1(13) . . . . ? C41A C35A N36 C46 171.4(8) . . . . ? C35A N36 C36A C37 -178.9(8) . . . . ? C46 N36 C36A C37 -14.4(12) . . . . ? C35A N36 C36A C40A -2.0(12) . . . . ? C46 N36 C36A C40A 162.5(8) . . . . ? C40A C36A C37 C38 -1.7(13) . . . . ? N36 C36A C37 C38 175.2(8) . . . . ? C36A C37 C38 C39 0.6(14) . . . . ? C37 C38 C39 C40 0.6(14) . . . . ? C38 C39 C40 C40A -0.8(14) . . . . ? C37 C36A C40A C40 1.5(13) . . . . ? N36 C36A C40A C40 -175.4(8) . . . . ? C37 C36A C40A C41 -176.6(8) . . . . ? N36 C36A C40A C41 6.5(13) . . . . ? C39 C40 C40A C36A -0.3(14) . . . . ? C39 C40 C40A C41 177.9(8) . . . . ? C36A C40A C41 O41 -170.8(9) . . . . ? C40 C40A C41 O41 11.0(13) . . . . ? C36A C40A C41 C41A 14.4(12) . . . . ? C40 C40A C41 C41A -163.8(8) . . . . ? O41 C41 C41A C35A 148.4(9) . . . . ? C40A C41 C41A C35A -36.9(10) . . . . ? O41 C41 C41A C41B 32.8(14) . . . . ? C40A C41 C41A C41B -152.4(8) . . . . ? O41 C41 C41A C42 -92.5(10) . . . . ? C40A C41 C41A C42 82.3(9) . . . . ? N35 C35A C41A C41 -135.4(9) . . . . ? N36 C35A C41A C41 44.2(11) . . . . ? N35 C35A C41A C41B -6.8(10) . . . . ? N36 C35A C41A C41B 172.8(8) . . . . ? N35 C35A C41A C42 109.6(9) . . . . ? N36 C35A C41A C42 -70.8(10) . . . . ? C32 C31 C41B C34A -2.9(14) . . . . ? Br31 C31 C41B C34A 173.5(7) . . . . ? C32 C31 C41B C41A -176.5(10) . . . . ? Br31 C31 C41B C41A -0.2(16) . . . . ? C34 C34A C41B C31 2.8(15) . . . . ? N35 C34A C41B C31 -179.5(8) . . . . ? C34 C34A C41B C41A 178.0(9) . . . . ? N35 C34A C41B C41A -4.3(11) . . . . ? C41 C41A C41B C31 -57.8(15) . . . . ? C35A C41A C41B C31 -179.9(11) . . . . ? C42 C41A C41B C31 64.0(14) . . . . ? C41 C41A C41B C34A 128.1(10) . . . . ? C35A C41A C41B C34A 6.0(9) . . . . ? C42 C41A C41B C34A -110.1(9) . . . . ? C41 C41A C42 C43 168.2(8) . . . . ? C35A C41A C42 C43 -71.8(9) . . . . ? C41B C41A C42 C43 36.7(11) . . . . ? C41A C42 C43 C44 -126.9(10) . . . . ? C42 C43 C44 C45 -174.5(8) . . . . ? C35A N36 C46 C47 97.6(10) . . . . ? C36A N36 C46 C47 -66.6(11) . . . . ? N36 C46 C47 C48 126.8(9) . . . . ? N36 C46 C47 C52 -59.5(12) . . . . ? C52 C47 C48 C49 1.9(14) . . . . ? C46 C47 C48 C49 175.8(10) . . . . ? C47 C48 C49 C50 -0.2(17) . . . . ? C48 C49 C50 C51 -3.2(16) . . . . ? C49 C50 C51 C52 5.1(15) . . . . ? C50 C51 C52 C47 -3.6(15) . . . . ? C48 C47 C52 C51 -0.1(14) . . . . ? C46 C47 C52 C51 -173.9(9) . . . . ? _diffrn_measured_fraction_theta_max 0.929 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.933 _refine_diff_density_max 1.054 _refine_diff_density_min -0.516 _refine_diff_density_rms 0.099 #===end