# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 188/239 data_compound4 _audit_creation_method SHELXL-97 _publ_contact_author ; Ryszard Gawinecki Department of Chemistry Technical and Agricultural University Seminaryjna 3 PL-85-326 Bydgoszcz Poland ; _publ_contact_author_email 'gawiner@chem.atr.bydgoszcz.pl' _publ_author_name ; Kolehmainen, E., Osmialowski, B., Krygowski, T. M., Kauppinen, R., Nissinen, M., Gawinecki, R. ; _publ_requested_journal_ 'J. Chem. Soc. Perkin 2' _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H15 N O' _chemical_formula_weight 261.31 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' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.354(1) _cell_length_b 12.314(1) _cell_length_c 29.346(1) _cell_angle_alpha 90.00 _cell_angle_beta 90.488(1) _cell_angle_gamma 90.00 _cell_volume 2657.4(4) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.306 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9531 _exptl_absorpt_correction_T_max 0.9840 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173.0(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6297 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0649 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_theta_min 3.23 _diffrn_reflns_theta_max 27.88 _reflns_number_total 6297 _reflns_number_gt 4101 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0322P)^2^+2.0460P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6297 _refine_ls_number_parameters 459 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1093 _refine_ls_R_factor_gt 0.0614 _refine_ls_wR_factor_ref 0.1522 _refine_ls_wR_factor_gt 0.1347 _refine_ls_goodness_of_fit_ref 1.110 _refine_ls_restrained_S_all 1.110 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C2 C 0.7832(3) 0.98178(18) 0.02490(8) 0.0301(5) Uani 1 1 d . . . C2B C 1.5588(3) 0.98331(19) 0.26791(8) 0.0320(5) Uani 1 1 d . . . C3 C 0.7450(3) 1.09316(19) 0.03589(9) 0.0361(6) Uani 1 1 d . . . C3B C 1.6365(3) 1.0894(2) 0.27408(9) 0.0374(6) Uani 1 1 d . . . C4 C 0.7778(3) 1.1327(2) 0.07807(9) 0.0358(6) Uani 1 1 d . . . C4B C 1.6779(3) 1.1268(2) 0.31643(9) 0.0373(6) Uani 1 1 d . . . C4A C 0.8567(3) 1.06563(19) 0.11286(8) 0.0315(5) Uani 1 1 d . . . C4AB C 1.6438(3) 1.06257(19) 0.35598(8) 0.0322(5) Uani 1 1 d . . . C5 C 0.8930(3) 1.1027(2) 0.15733(8) 0.0358(5) Uani 1 1 d . . . C5B C 1.6834(3) 1.0970(2) 0.40060(9) 0.0379(6) Uani 1 1 d . . . C6 C 0.9735(3) 1.0355(2) 0.18913(9) 0.0395(6) Uani 1 1 d . . . C6B C 1.6431(3) 1.0323(2) 0.43751(9) 0.0400(6) Uani 1 1 d . . . C7 C 1.0193(3) 0.9291(2) 0.17701(8) 0.0375(6) Uani 1 1 d . . . C7B C 1.5613(3) 0.9303(2) 0.43034(9) 0.0388(6) Uani 1 1 d . . . C8 C 0.9841(3) 0.8907(2) 0.13395(8) 0.0338(5) Uani 1 1 d . . . C8B C 1.5224(3) 0.8942(2) 0.38693(8) 0.0332(5) Uani 1 1 d . . . C8A C 0.9016(3) 0.95842(18) 0.10149(7) 0.0282(5) Uani 1 1 d . . . C8AB C 1.5635(3) 0.95981(18) 0.34963(8) 0.0300(5) Uani 1 1 d . . . C9 C 0.7359(3) 0.93566(19) -0.01682(8) 0.0323(5) Uani 1 1 d . . . C9B C 1.5211(3) 0.9394(2) 0.22499(8) 0.0349(5) Uani 1 1 d . . . C10 C 0.7506(3) 0.82369(19) -0.02618(7) 0.0315(5) Uani 1 1 d . . . C10B C 1.4538(3) 0.83389(19) 0.21863(8) 0.0319(5) Uani 1 1 d . . . C1' C 0.6800(3) 0.78102(18) -0.07046(7) 0.0283(5) Uani 1 1 d . . . C1'B C 1.4212(3) 0.78949(18) 0.17183(7) 0.0297(5) Uani 1 1 d . . . C2' C 0.6877(3) 0.84142(19) -0.11078(8) 0.0313(5) Uani 1 1 d . . . C2'B C 1.4726(3) 0.8434(2) 0.13202(8) 0.0330(5) Uani 1 1 d . . . C3' C 0.6292(3) 0.7961(2) -0.15179(8) 0.0340(5) Uani 1 1 d . . . C3'B C 1.4417(3) 0.7983(2) 0.08968(8) 0.0342(5) Uani 1 1 d . . . C4' C 0.5559(3) 0.6924(2) -0.15369(8) 0.0347(5) Uani 1 1 d . . . C4'B C 1.3567(3) 0.6970(2) 0.08513(8) 0.0341(5) Uani 1 1 d . . . C5' C 0.5426(3) 0.6338(2) -0.11319(8) 0.0338(5) Uani 1 1 d . . . C5'B C 1.3038(3) 0.6440(2) 0.12467(8) 0.0344(5) Uani 1 1 d . . . C6' C 0.6073(3) 0.67657(19) -0.07244(8) 0.0318(5) Uani 1 1 d . . . C6'B C 1.3361(3) 0.68873(19) 0.16732(8) 0.0324(5) Uani 1 1 d . . . C12 C 0.4976(4) 0.6429(2) -0.19852(8) 0.0480(7) Uani 1 1 d . . . H12A H 0.3806 0.6739 -0.2080 0.072 Uiso 1 1 calc R . . H12B H 0.4852 0.5641 -0.1950 0.072 Uiso 1 1 calc R . . H12C H 0.5893 0.6585 -0.2217 0.072 Uiso 1 1 calc R . . C12B C 1.3232(4) 0.6473(2) 0.03906(9) 0.0507(7) Uani 1 1 d . . . H12D H 1.3169 0.5681 0.0420 0.076 Uiso 1 1 calc R . . H12E H 1.4228 0.6667 0.0186 0.076 Uiso 1 1 calc R . . H12F H 1.2081 0.6746 0.0265 0.076 Uiso 1 1 calc R . . H1 H 0.875(3) 0.849(2) 0.0508(9) 0.048(8) Uiso 1 1 d . . . H1B H 1.470(4) 0.848(3) 0.2972(11) 0.084(10) Uiso 1 1 d . . . H3B H 1.660(3) 1.135(2) 0.2444(9) 0.048(7) Uiso 1 1 d . . . H3 H 0.689(3) 1.142(2) 0.0122(9) 0.049(7) Uiso 1 1 d . . . H4B H 1.732(3) 1.202(2) 0.3205(8) 0.043(7) Uiso 1 1 d . . . H4 H 0.751(3) 1.205(2) 0.0856(8) 0.039(7) Uiso 1 1 d . . . H5 H 0.857(3) 1.178(2) 0.1655(8) 0.039(7) Uiso 1 1 d . . . H6 H 0.999(3) 1.063(2) 0.2203(9) 0.047(7) Uiso 1 1 d . . . H6B H 1.671(3) 1.059(2) 0.4697(8) 0.041(7) Uiso 1 1 d . . . H7B H 1.528(3) 0.884(2) 0.4565(9) 0.049(7) Uiso 1 1 d . . . H7 H 1.078(3) 0.879(2) 0.1993(8) 0.045(7) Uiso 1 1 d . . . H8 H 1.016(3) 0.8155(19) 0.1251(7) 0.030(6) Uiso 1 1 d . . . H8B H 1.463(3) 0.825(2) 0.3826(8) 0.036(6) Uiso 1 1 d . . . H9 H 0.679(3) 0.982(2) -0.0385(8) 0.039(7) Uiso 1 1 d . . . H9B H 1.553(3) 0.983(2) 0.1987(9) 0.044(7) Uiso 1 1 d . . . H2' H 0.736(3) 0.918(2) -0.1099(8) 0.038(6) Uiso 1 1 d . . . H2'B H 1.532(3) 0.9104(19) 0.1336(7) 0.027(6) Uiso 1 1 d . . . H3'B H 1.481(3) 0.833(2) 0.0614(9) 0.044(7) Uiso 1 1 d . . . H3' H 0.636(3) 0.838(2) -0.1801(9) 0.044(7) Uiso 1 1 d . . . H5B H 1.740(3) 1.173(2) 0.4048(9) 0.052(8) Uiso 1 1 d . . . H5' H 0.491(3) 0.561(2) -0.1147(8) 0.045(7) Uiso 1 1 d . . . H5'B H 1.243(3) 0.574(2) 0.1226(8) 0.046(7) Uiso 1 1 d . . . H6' H 0.603(3) 0.634(2) -0.0432(9) 0.050(7) Uiso 1 1 d . . . H6'B H 1.301(3) 0.646(2) 0.1959(8) 0.041(7) Uiso 1 1 d . . . O11 O 0.8157(2) 0.75649(13) 0.00237(5) 0.0378(4) Uani 1 1 d . . . O11B O 1.4167(2) 0.77132(14) 0.25220(5) 0.0411(4) Uani 1 1 d . . . N1 N 0.8620(2) 0.92058(16) 0.05824(6) 0.0294(4) Uani 1 1 d . . . N1B N 1.5229(2) 0.92429(16) 0.30603(6) 0.0316(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 C2 0.0284(11) 0.0264(12) 0.0355(13) 0.0011(10) -0.0019(9) -0.0006(9) C2B 0.0292(11) 0.0307(13) 0.0360(13) 0.0015(10) 0.0013(9) 0.0007(9) C3 0.0384(13) 0.0274(13) 0.0424(15) 0.0004(11) -0.0075(10) 0.0023(10) C3B 0.0373(13) 0.0315(13) 0.0434(15) 0.0026(11) 0.0031(10) -0.0037(10) C4 0.0361(12) 0.0240(13) 0.0474(15) -0.0038(11) -0.0032(10) -0.0003(10) C4B 0.0318(12) 0.0295(13) 0.0506(16) -0.0048(12) 0.0036(10) -0.0055(10) C4A 0.0265(11) 0.0322(13) 0.0359(13) -0.0030(10) 0.0017(9) -0.0028(9) C4AB 0.0263(11) 0.0300(13) 0.0402(14) -0.0042(10) 0.0009(9) -0.0002(9) C5 0.0323(12) 0.0366(14) 0.0385(14) -0.0077(11) 0.0046(10) -0.0035(10) C5B 0.0328(12) 0.0326(14) 0.0483(16) -0.0082(12) -0.0034(10) -0.0023(10) C6 0.0352(13) 0.0506(16) 0.0326(14) -0.0063(12) 0.0017(10) -0.0025(11) C6B 0.0379(13) 0.0420(15) 0.0401(15) -0.0099(12) -0.0047(10) 0.0008(11) C7 0.0350(12) 0.0489(16) 0.0286(13) 0.0019(12) -0.0003(9) 0.0041(11) C7B 0.0394(13) 0.0379(14) 0.0391(15) -0.0021(12) 0.0004(10) 0.0013(11) C8 0.0334(12) 0.0335(14) 0.0344(13) -0.0003(11) -0.0004(9) 0.0032(10) C8B 0.0317(12) 0.0295(13) 0.0383(14) -0.0038(11) -0.0002(9) -0.0020(10) C8A 0.0237(10) 0.0305(12) 0.0303(12) -0.0006(10) 0.0006(8) -0.0024(9) C8AB 0.0251(10) 0.0297(12) 0.0353(13) -0.0036(10) -0.0010(9) 0.0009(9) C9 0.0347(12) 0.0294(12) 0.0327(13) 0.0025(10) -0.0062(9) 0.0023(10) C9B 0.0368(12) 0.0324(13) 0.0357(14) 0.0045(11) 0.0000(10) -0.0019(10) C10 0.0316(11) 0.0332(13) 0.0295(12) 0.0015(10) 0.0003(9) 0.0024(10) C10B 0.0289(11) 0.0332(13) 0.0336(13) 0.0028(10) 0.0006(9) 0.0021(9) C1' 0.0293(11) 0.0278(12) 0.0277(12) -0.0014(9) 0.0016(8) 0.0032(9) C1'B 0.0250(10) 0.0307(12) 0.0335(12) 0.0024(10) 0.0010(8) 0.0025(9) C2' 0.0323(11) 0.0304(13) 0.0314(12) 0.0023(10) -0.0001(9) 0.0004(10) C2'B 0.0308(12) 0.0289(13) 0.0394(14) 0.0022(10) -0.0009(9) -0.0026(10) C3' 0.0345(12) 0.0399(14) 0.0275(12) 0.0036(11) -0.0002(9) -0.0014(10) C3'B 0.0346(12) 0.0348(14) 0.0331(13) 0.0038(11) 0.0029(9) 0.0008(10) C4' 0.0294(11) 0.0408(14) 0.0339(13) -0.0043(11) 0.0002(9) -0.0002(10) C4'B 0.0323(11) 0.0368(14) 0.0331(13) 0.0001(11) 0.0011(9) 0.0020(10) C5' 0.0350(12) 0.0287(13) 0.0378(14) -0.0046(11) 0.0035(10) -0.0025(10) C5'B 0.0327(12) 0.0297(13) 0.0408(14) -0.0008(11) 0.0023(10) -0.0018(10) C6' 0.0342(12) 0.0299(13) 0.0315(13) 0.0027(10) 0.0041(9) 0.0019(10) C6'B 0.0318(11) 0.0315(13) 0.0340(13) 0.0059(11) 0.0027(9) 0.0013(10) C12 0.0486(15) 0.0587(18) 0.0366(14) -0.0078(13) -0.0040(11) -0.0114(13) C12B 0.0652(18) 0.0483(17) 0.0387(15) -0.0059(13) 0.0042(12) -0.0102(14) O11 0.0537(10) 0.0287(9) 0.0308(9) 0.0013(7) -0.0051(7) 0.0066(7) O11B 0.0537(10) 0.0361(10) 0.0335(9) 0.0054(8) 0.0010(7) -0.0086(8) N1 0.0306(9) 0.0261(11) 0.0315(11) -0.0008(8) -0.0021(7) 0.0012(8) N1B 0.0315(10) 0.0279(11) 0.0355(11) 0.0001(9) -0.0005(8) -0.0029(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C2 N1 1.360(3) . ? C2 C9 1.391(3) . ? C2 C3 1.437(3) . ? C2B N1B 1.362(3) . ? C2B C9B 1.396(3) . ? C2B C3B 1.437(3) . ? C3 C4 1.350(3) . ? C3B C4B 1.357(3) . ? C4 C4A 1.432(3) . ? C4B C4AB 1.428(3) . ? C4A C8A 1.402(3) . ? C4A C5 1.406(3) . ? C4AB C5B 1.405(3) . ? C4AB C8AB 1.408(3) . ? C5 C6 1.377(4) . ? C5B C6B 1.379(4) . ? C6 C7 1.399(4) . ? C6B C7B 1.408(4) . ? C7 C8 1.372(3) . ? C7B C8B 1.377(3) . ? C8 C8A 1.400(3) . ? C8B C8AB 1.396(3) . ? C8A N1 1.381(3) . ? C8AB N1B 1.382(3) . ? C9 C10 1.410(3) . ? C9B C10B 1.402(3) . ? C10 O11 1.268(3) . ? C10 C1' 1.491(3) . ? C10B O11B 1.282(3) . ? C10B C1'B 1.496(3) . ? C1' C6' 1.394(3) . ? C1' C2' 1.399(3) . ? C1'B C6'B 1.395(3) . ? C1'B C2'B 1.399(3) . ? C2' C3' 1.392(3) . ? C2'B C3'B 1.378(3) . ? C3' C4' 1.387(3) . ? C3'B C4'B 1.401(3) . ? C4' C5' 1.394(3) . ? C4' C12 1.509(3) . ? C4'B C5'B 1.390(3) . ? C4'B C12B 1.502(3) . ? C5' C6' 1.387(3) . ? C5'B C6'B 1.386(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C2 C9 120.6(2) . . ? N1 C2 C3 116.7(2) . . ? C9 C2 C3 122.6(2) . . ? N1B C2B C9B 119.7(2) . . ? N1B C2B C3B 117.5(2) . . ? C9B C2B C3B 122.8(2) . . ? C4 C3 C2 121.1(2) . . ? C4B C3B C2B 120.6(2) . . ? C3 C4 C4A 120.9(2) . . ? C3B C4B C4AB 121.1(2) . . ? C8A C4A C5 118.9(2) . . ? C8A C4A C4 117.9(2) . . ? C5 C4A C4 123.2(2) . . ? C5B C4AB C8AB 118.6(2) . . ? C5B C4AB C4B 123.6(2) . . ? C8AB C4AB C4B 117.8(2) . . ? C6 C5 C4A 120.7(2) . . ? C6B C5B C4AB 120.9(2) . . ? C5 C6 C7 119.6(2) . . ? C5B C6B C7B 119.5(2) . . ? C8 C7 C6 120.9(2) . . ? C8B C7B C6B 120.8(2) . . ? C7 C8 C8A 119.8(2) . . ? C7B C8B C8AB 119.6(2) . . ? N1 C8A C8 120.7(2) . . ? N1 C8A C4A 119.2(2) . . ? C8 C8A C4A 120.1(2) . . ? N1B C8AB C8B 119.8(2) . . ? N1B C8AB C4AB 119.6(2) . . ? C8B C8AB C4AB 120.7(2) . . ? C2 C9 C10 123.5(2) . . ? C2B C9B C10B 123.1(2) . . ? O11 C10 C9 122.6(2) . . ? O11 C10 C1' 118.2(2) . . ? C9 C10 C1' 119.2(2) . . ? O11B C10B C9B 122.1(2) . . ? O11B C10B C1'B 116.9(2) . . ? C9B C10B C1'B 121.0(2) . . ? C6' C1' C2' 118.3(2) . . ? C6' C1' C10 119.5(2) . . ? C2' C1' C10 122.2(2) . . ? C6'B C1'B C2'B 117.8(2) . . ? C6'B C1'B C10B 118.7(2) . . ? C2'B C1'B C10B 123.4(2) . . ? C3' C2' C1' 120.3(2) . . ? C3'B C2'B C1'B 121.2(2) . . ? C4' C3' C2' 121.4(2) . . ? C2'B C3'B C4'B 121.0(2) . . ? C3' C4' C5' 118.2(2) . . ? C3' C4' C12 121.0(2) . . ? C5' C4' C12 120.8(2) . . ? C5'B C4'B C3'B 117.8(2) . . ? C5'B C4'B C12B 121.0(2) . . ? C3'B C4'B C12B 121.2(2) . . ? C6' C5' C4' 120.8(2) . . ? C6'B C5'B C4'B 121.3(2) . . ? C5' C6' C1' 121.0(2) . . ? C5'B C6'B C1'B 120.8(2) . . ? C2 N1 C8A 124.0(2) . . ? C2B N1B C8AB 123.3(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 N1 C2 C3 C4 -3.2(3) . . . . ? C9 C2 C3 C4 173.9(2) . . . . ? N1B C2B C3B C4B 2.3(3) . . . . ? C9B C2B C3B C4B -177.1(2) . . . . ? C2 C3 C4 C4A 1.8(4) . . . . ? C2B C3B C4B C4AB -0.7(4) . . . . ? C3 C4 C4A C8A 1.1(3) . . . . ? C3 C4 C4A C5 -179.8(2) . . . . ? C3B C4B C4AB C5B -179.9(2) . . . . ? C3B C4B C4AB C8AB -0.8(3) . . . . ? C8A C4A C5 C6 0.8(3) . . . . ? C4 C4A C5 C6 -178.3(2) . . . . ? C8AB C4AB C5B C6B -0.7(3) . . . . ? C4B C4AB C5B C6B 178.4(2) . . . . ? C4A C5 C6 C7 -0.1(3) . . . . ? C4AB C5B C6B C7B 0.1(4) . . . . ? C5 C6 C7 C8 -0.3(4) . . . . ? C5B C6B C7B C8B 0.4(4) . . . . ? C6 C7 C8 C8A 0.1(4) . . . . ? C6B C7B C8B C8AB -0.4(4) . . . . ? C7 C8 C8A N1 -178.8(2) . . . . ? C7 C8 C8A C4A 0.6(3) . . . . ? C5 C4A C8A N1 178.32(19) . . . . ? C4 C4A C8A N1 -2.6(3) . . . . ? C5 C4A C8A C8 -1.1(3) . . . . ? C4 C4A C8A C8 178.1(2) . . . . ? C7B C8B C8AB N1B -179.4(2) . . . . ? C7B C8B C8AB C4AB -0.2(3) . . . . ? C5B C4AB C8AB N1B 179.9(2) . . . . ? C4B C4AB C8AB N1B 0.8(3) . . . . ? C5B C4AB C8AB C8B 0.7(3) . . . . ? C4B C4AB C8AB C8B -178.4(2) . . . . ? N1 C2 C9 C10 5.5(3) . . . . ? C3 C2 C9 C10 -171.5(2) . . . . ? N1B C2B C9B C10B -2.7(3) . . . . ? C3B C2B C9B C10B 176.7(2) . . . . ? C2 C9 C10 O11 -3.0(4) . . . . ? C2 C9 C10 C1' 174.3(2) . . . . ? C2B C9B C10B O11B 2.2(4) . . . . ? C2B C9B C10B C1'B -178.1(2) . . . . ? O11 C10 C1' C6' 29.9(3) . . . . ? C9 C10 C1' C6' -147.4(2) . . . . ? O11 C10 C1' C2' -148.5(2) . . . . ? C9 C10 C1' C2' 34.2(3) . . . . ? O11B C10B C1'B C6'B 6.5(3) . . . . ? C9B C10B C1'B C6'B -173.3(2) . . . . ? O11B C10B C1'B C2'B -173.1(2) . . . . ? C9B C10B C1'B C2'B 7.2(3) . . . . ? C6' C1' C2' C3' -2.0(3) . . . . ? C10 C1' C2' C3' 176.5(2) . . . . ? C6'B C1'B C2'B C3'B -0.5(3) . . . . ? C10B C1'B C2'B C3'B 179.1(2) . . . . ? C1' C2' C3' C4' 2.4(3) . . . . ? C1'B C2'B C3'B C4'B 0.3(3) . . . . ? C2' C3' C4' C5' -0.2(3) . . . . ? C2' C3' C4' C12 -178.3(2) . . . . ? C2'B C3'B C4'B C5'B 0.3(3) . . . . ? C2'B C3'B C4'B C12B -179.8(2) . . . . ? C3' C4' C5' C6' -2.4(3) . . . . ? C12 C4' C5' C6' 175.7(2) . . . . ? C3'B C4'B C5'B C6'B -0.9(3) . . . . ? C12B C4'B C5'B C6'B 179.3(2) . . . . ? C4' C5' C6' C1' 2.8(3) . . . . ? C2' C1' C6' C5' -0.6(3) . . . . ? C10 C1' C6' C5' -179.1(2) . . . . ? C4'B C5'B C6'B C1'B 0.7(3) . . . . ? C2'B C1'B C6'B C5'B 0.0(3) . . . . ? C10B C1'B C6'B C5'B -179.7(2) . . . . ? C9 C2 N1 C8A -175.5(2) . . . . ? C3 C2 N1 C8A 1.8(3) . . . . ? C8 C8A N1 C2 -179.5(2) . . . . ? C4A C8A N1 C2 1.1(3) . . . . ? C9B C2B N1B C8AB 177.1(2) . . . . ? C3B C2B N1B C8AB -2.4(3) . . . . ? C8B C8AB N1B C2B -179.9(2) . . . . ? C4AB C8AB N1B C2B 0.9(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O11 0.91(3) 1.87(3) 2.622(2) 138(2) . N1B H1B O11B 1.04(3) 1.67(3) 2.575(3) 142(3) . _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.88 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.266 _refine_diff_density_min -0.231 _refine_diff_density_rms 0.048 #===END data_COMPOUND5 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point '135-137' _chemical_formula_moiety ? _chemical_formula_sum 'C18 H15 N O' _chemical_formula_weight 261.31 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' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/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 7.2831(1) _cell_length_b 14.4511(5) _cell_length_c 12.5032(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.693(2) _cell_angle_gamma 90.00 _cell_volume 1315.85(6) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.319 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9527 _exptl_absorpt_correction_T_max 0.9681 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173.0(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3101 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0375 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.13 _diffrn_reflns_theta_max 27.87 _reflns_number_total 3101 _reflns_number_gt 2590 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0484P)^2^+0.5321P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3101 _refine_ls_number_parameters 230 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0585 _refine_ls_R_factor_gt 0.0460 _refine_ls_wR_factor_ref 0.1178 _refine_ls_wR_factor_gt 0.1102 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C2 C 0.71392(17) 0.04027(9) 0.01734(10) 0.0226(3) Uani 1 1 d . . . C3 C 0.75837(19) 0.06046(10) -0.09186(10) 0.0271(3) Uani 1 1 d . . . C4 C 0.74695(18) 0.14765(10) -0.13016(10) 0.0267(3) Uani 1 1 d . . . C5 C 0.68554(16) 0.22217(9) -0.06414(10) 0.0226(3) Uani 1 1 d . . . C6 C 0.68217(18) 0.31505(10) -0.09694(11) 0.0277(3) Uani 1 1 d . . . C7 C 0.6243(2) 0.38351(10) -0.02854(12) 0.0311(3) Uani 1 1 d . . . C8 C 0.5630(2) 0.36065(10) 0.07398(11) 0.0303(3) Uani 1 1 d . . . C9 C 0.56356(18) 0.26982(9) 0.10795(10) 0.0255(3) Uani 1 1 d . . . C10 C 0.62935(16) 0.20055(9) 0.04050(10) 0.0212(3) Uani 1 1 d . . . C11 C 0.74744(18) -0.04586(9) 0.06457(10) 0.0248(3) Uani 1 1 d . . . C12 C 0.72918(17) -0.06131(9) 0.17535(10) 0.0236(3) Uani 1 1 d . . . C13 C 0.79551(17) -0.15128(9) 0.22121(10) 0.0233(3) Uani 1 1 d . . . C14 C 0.78858(17) -0.23398(9) 0.16387(10) 0.0245(3) Uani 1 1 d . . . C15 C 0.85613(18) -0.31634(10) 0.20749(11) 0.0273(3) Uani 1 1 d . . . C16 C 0.93441(18) -0.31345(10) 0.31025(11) 0.0294(3) Uani 1 1 d . . . C17 C 0.94100(19) -0.23183(10) 0.36828(11) 0.0292(3) Uani 1 1 d . . . C18 C 0.87032(18) -0.15082(10) 0.32477(10) 0.0262(3) Uani 1 1 d . . . C19 C 0.8454(2) -0.40578(10) 0.14590(13) 0.0393(4) Uani 1 1 d . . . H19A H 0.7351 -0.4399 0.1667 0.059 Uiso 1 1 calc R . . H19B H 0.9544 -0.4433 0.1618 0.059 Uiso 1 1 calc R . . H19C H 0.8396 -0.3924 0.0691 0.059 Uiso 1 1 calc R . . O1 O 0.66784(14) -0.00078(7) 0.23930(7) 0.0303(2) Uani 1 1 d . . . N1 N 0.64507(14) 0.11057(7) 0.07638(8) 0.0219(2) Uani 1 1 d . . . H9 H 0.521(2) 0.2524(11) 0.1788(12) 0.027(4) Uiso 1 1 d . . . H11 H 0.797(2) -0.0944(12) 0.0190(12) 0.032(4) Uiso 1 1 d . . . H16 H 0.988(2) -0.3717(12) 0.3404(14) 0.041(5) Uiso 1 1 d . . . H18 H 0.877(2) -0.0924(12) 0.3656(13) 0.038(4) Uiso 1 1 d . . . H14 H 0.733(2) -0.2350(11) 0.0905(13) 0.032(4) Uiso 1 1 d . . . H4 H 0.780(2) 0.1631(12) -0.2032(14) 0.037(4) Uiso 1 1 d . . . H3 H 0.803(2) 0.0072(12) -0.1359(13) 0.039(5) Uiso 1 1 d . . . H17 H 0.995(2) -0.2307(12) 0.4408(14) 0.040(5) Uiso 1 1 d . . . H8 H 0.519(2) 0.4114(13) 0.1230(14) 0.042(5) Uiso 1 1 d . . . H1 H 0.622(2) 0.0940(13) 0.1478(15) 0.046(5) Uiso 1 1 d . . . H6 H 0.724(2) 0.3307(12) -0.1698(13) 0.036(4) Uiso 1 1 d . . . H7 H 0.628(2) 0.4501(13) -0.0502(13) 0.041(5) 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 C2 0.0227(6) 0.0241(6) 0.0210(6) -0.0015(5) -0.0010(5) 0.0021(5) C3 0.0319(7) 0.0287(7) 0.0207(6) -0.0007(5) 0.0018(5) 0.0067(5) C4 0.0278(7) 0.0322(7) 0.0201(6) 0.0023(5) 0.0022(5) 0.0047(5) C5 0.0193(6) 0.0261(7) 0.0223(6) 0.0033(5) -0.0002(4) 0.0011(5) C6 0.0271(7) 0.0291(7) 0.0269(7) 0.0070(6) 0.0015(5) 0.0011(5) C7 0.0329(7) 0.0242(7) 0.0363(8) 0.0069(6) 0.0009(6) 0.0021(6) C8 0.0320(7) 0.0255(7) 0.0335(7) -0.0005(6) 0.0019(6) 0.0049(6) C9 0.0272(6) 0.0249(7) 0.0245(6) 0.0005(5) 0.0023(5) 0.0027(5) C10 0.0189(6) 0.0220(6) 0.0227(6) 0.0014(5) -0.0017(4) 0.0009(5) C11 0.0297(7) 0.0215(6) 0.0232(6) -0.0010(5) 0.0012(5) 0.0036(5) C12 0.0247(6) 0.0214(6) 0.0246(6) 0.0000(5) 0.0007(5) -0.0009(5) C13 0.0228(6) 0.0242(7) 0.0229(6) 0.0031(5) 0.0025(5) -0.0011(5) C14 0.0238(6) 0.0250(7) 0.0248(6) 0.0026(5) 0.0001(5) -0.0001(5) C15 0.0255(6) 0.0242(7) 0.0322(7) 0.0033(5) 0.0023(5) -0.0005(5) C16 0.0252(7) 0.0293(7) 0.0335(7) 0.0113(6) 0.0002(5) 0.0013(5) C17 0.0264(7) 0.0361(8) 0.0252(7) 0.0068(6) -0.0017(5) -0.0006(6) C18 0.0261(7) 0.0286(7) 0.0241(6) 0.0009(5) 0.0022(5) -0.0021(5) C19 0.0478(9) 0.0243(7) 0.0459(9) 0.0013(7) -0.0048(7) 0.0017(6) O1 0.0437(6) 0.0238(5) 0.0234(5) -0.0011(4) 0.0049(4) 0.0039(4) N1 0.0250(5) 0.0213(5) 0.0193(5) 0.0010(4) 0.0016(4) 0.0017(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 C2 N1 1.3555(16) . ? C2 C11 1.3979(18) . ? C2 C3 1.4370(17) . ? C3 C4 1.350(2) . ? C4 C5 1.4317(18) . ? C5 C6 1.4036(19) . ? C5 C10 1.4106(17) . ? C6 C7 1.377(2) . ? C7 C8 1.402(2) . ? C8 C9 1.3797(19) . ? C9 C10 1.3974(18) . ? C10 N1 1.3797(16) . ? C11 C12 1.4109(18) . ? C12 O1 1.2699(16) . ? C12 C13 1.4986(18) . ? C13 C14 1.3943(19) . ? C13 C18 1.3987(18) . ? C14 C15 1.3961(19) . ? C15 C16 1.4000(19) . ? C15 C19 1.506(2) . ? C16 C17 1.385(2) . ? C17 C18 1.387(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C2 C11 120.08(11) . . ? N1 C2 C3 117.02(12) . . ? C11 C2 C3 122.82(12) . . ? C4 C3 C2 120.85(12) . . ? C3 C4 C5 121.05(12) . . ? C6 C5 C10 118.59(12) . . ? C6 C5 C4 123.73(12) . . ? C10 C5 C4 117.66(12) . . ? C7 C6 C5 120.66(12) . . ? C6 C7 C8 120.12(13) . . ? C9 C8 C7 120.39(13) . . ? C8 C9 C10 119.70(12) . . ? N1 C10 C9 120.44(11) . . ? N1 C10 C5 119.11(11) . . ? C9 C10 C5 120.43(12) . . ? C2 C11 C12 122.52(12) . . ? O1 C12 C11 123.17(12) . . ? O1 C12 C13 118.09(11) . . ? C11 C12 C13 118.63(11) . . ? C14 C13 C18 119.43(12) . . ? C14 C13 C12 122.51(11) . . ? C18 C13 C12 118.05(12) . . ? C13 C14 C15 121.30(12) . . ? C14 C15 C16 118.08(13) . . ? C14 C15 C19 121.06(12) . . ? C16 C15 C19 120.86(13) . . ? C17 C16 C15 121.14(13) . . ? C16 C17 C18 120.18(13) . . ? C17 C18 C13 119.84(13) . . ? C2 N1 C10 123.99(11) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C2 C3 C4 5.73(19) . . . . ? C11 C2 C3 C4 -170.98(13) . . . . ? C2 C3 C4 C5 -1.7(2) . . . . ? C3 C4 C5 C6 175.64(13) . . . . ? C3 C4 C5 C10 -2.90(19) . . . . ? C10 C5 C6 C7 -0.3(2) . . . . ? C4 C5 C6 C7 -178.86(13) . . . . ? C5 C6 C7 C8 -1.8(2) . . . . ? C6 C7 C8 C9 1.3(2) . . . . ? C7 C8 C9 C10 1.4(2) . . . . ? C8 C9 C10 N1 174.61(12) . . . . ? C8 C9 C10 C5 -3.6(2) . . . . ? C6 C5 C10 N1 -175.17(11) . . . . ? C4 C5 C10 N1 3.44(17) . . . . ? C6 C5 C10 C9 3.02(18) . . . . ? C4 C5 C10 C9 -178.37(12) . . . . ? N1 C2 C11 C12 -6.3(2) . . . . ? C3 C2 C11 C12 170.35(13) . . . . ? C2 C11 C12 O1 5.6(2) . . . . ? C2 C11 C12 C13 -170.70(12) . . . . ? O1 C12 C13 C14 150.94(13) . . . . ? C11 C12 C13 C14 -32.62(18) . . . . ? O1 C12 C13 C18 -30.40(17) . . . . ? C11 C12 C13 C18 146.04(13) . . . . ? C18 C13 C14 C15 -0.5(2) . . . . ? C12 C13 C14 C15 178.16(11) . . . . ? C13 C14 C15 C16 -1.08(19) . . . . ? C13 C14 C15 C19 178.95(13) . . . . ? C14 C15 C16 C17 1.5(2) . . . . ? C19 C15 C16 C17 -178.53(13) . . . . ? C15 C16 C17 C18 -0.3(2) . . . . ? C16 C17 C18 C13 -1.3(2) . . . . ? C14 C13 C18 C17 1.66(19) . . . . ? C12 C13 C18 C17 -177.04(12) . . . . ? C11 C2 N1 C10 171.52(12) . . . . ? C3 C2 N1 C10 -5.29(18) . . . . ? C9 C10 N1 C2 -177.44(12) . . . . ? C5 C10 N1 C2 0.75(18) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O1 0.942(18) 1.813(19) 2.5997(14) 139.1(16) . _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.87 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.245 _refine_diff_density_min -0.248 _refine_diff_density_rms 0.043 #===END data_compound5(r.t.) _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point '135-137' _chemical_formula_moiety ? _chemical_formula_sum 'C18 H15 N O' _chemical_formula_weight 261.31 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' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/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 7.3719(2) _cell_length_b 14.4550(4) _cell_length_c 12.5837(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.736(2) _cell_angle_gamma 90.00 _cell_volume 1340.82(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.294 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9611 _exptl_absorpt_correction_T_max 0.9687 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3089 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0368 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 27.88 _reflns_number_total 3089 _reflns_number_gt 2350 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0630P)^2^+0.2796P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3089 _refine_ls_number_parameters 230 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0719 _refine_ls_R_factor_gt 0.0508 _refine_ls_wR_factor_ref 0.1336 _refine_ls_wR_factor_gt 0.1196 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C2 C 0.71402(19) 0.04005(10) 0.01845(11) 0.0388(3) Uani 1 1 d . . . C3 C 0.7585(2) 0.06045(12) -0.08955(11) 0.0474(4) Uani 1 1 d . . . C4 C 0.7468(2) 0.14702(11) -0.12781(11) 0.0464(4) Uani 1 1 d . . . C5 C 0.68612(18) 0.22138(10) -0.06249(11) 0.0393(3) Uani 1 1 d . . . C6 C 0.6820(2) 0.31402(11) -0.09518(13) 0.0481(4) Uani 1 1 d . . . C7 C 0.6242(2) 0.38236(12) -0.02777(14) 0.0536(4) Uani 1 1 d . . . C8 C 0.5640(2) 0.35961(11) 0.07366(13) 0.0518(4) Uani 1 1 d . . . C9 C 0.5652(2) 0.26926(10) 0.10777(12) 0.0439(4) Uani 1 1 d . . . C10 C 0.63054(18) 0.19972(9) 0.04103(10) 0.0365(3) Uani 1 1 d . . . C11 C 0.7473(2) -0.04612(10) 0.06542(11) 0.0423(3) Uani 1 1 d . . . C12 C 0.7298(2) -0.06216(10) 0.17476(11) 0.0407(3) Uani 1 1 d . . . C13 C 0.79548(19) -0.15188(10) 0.22028(11) 0.0397(3) Uani 1 1 d . . . C14 C 0.7887(2) -0.23447(10) 0.16369(12) 0.0421(3) Uani 1 1 d . . . C15 C 0.8559(2) -0.31663(11) 0.20642(12) 0.0468(4) Uani 1 1 d . . . C16 C 0.9333(2) -0.31370(12) 0.30802(13) 0.0509(4) Uani 1 1 d . . . C17 C 0.9395(2) -0.23260(12) 0.36550(13) 0.0505(4) Uani 1 1 d . . . C18 C 0.8697(2) -0.15169(11) 0.32291(12) 0.0450(4) Uani 1 1 d . . . C19 C 0.8460(3) -0.40568(12) 0.14487(16) 0.0680(5) Uani 1 1 d . . . H19A H 0.7348 -0.4370 0.1606 0.102 Uiso 1 1 calc R . . H19B H 0.9469 -0.4443 0.1645 0.102 Uiso 1 1 calc R . . H19C H 0.8501 -0.3925 0.0702 0.102 Uiso 1 1 calc R . . O1 O 0.66934(16) -0.00173(7) 0.23871(8) 0.0520(3) Uani 1 1 d . . . N1 N 0.64619(16) 0.11010(8) 0.07730(9) 0.0377(3) Uani 1 1 d . . . H9 H 0.525(2) 0.2515(11) 0.1783(13) 0.052(5) Uiso 1 1 d . . . H14 H 0.735(2) -0.2368(12) 0.0918(13) 0.053(5) Uiso 1 1 d . . . H11 H 0.796(2) -0.0941(12) 0.0205(13) 0.056(5) Uiso 1 1 d . . . H16 H 0.985(3) -0.3717(13) 0.3367(14) 0.062(5) Uiso 1 1 d . . . H18 H 0.875(2) -0.0932(12) 0.3629(13) 0.057(5) Uiso 1 1 d . . . H4 H 0.781(2) 0.1620(11) -0.1994(14) 0.054(5) Uiso 1 1 d . . . H17 H 0.992(2) -0.2311(12) 0.4359(15) 0.061(5) Uiso 1 1 d . . . H5 H 0.719(3) 0.3284(12) -0.1665(14) 0.060(5) Uiso 1 1 d . . . H7 H 0.523(3) 0.4098(13) 0.1238(14) 0.064(5) Uiso 1 1 d . . . H3 H 0.799(2) 0.0058(13) -0.1343(14) 0.064(5) Uiso 1 1 d . . . H6 H 0.625(3) 0.4486(15) -0.0492(15) 0.075(6) Uiso 1 1 d . . . H1 H 0.624(3) 0.0887(14) 0.1539(16) 0.081(6) 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 C2 0.0409(7) 0.0397(8) 0.0359(7) -0.0014(6) 0.0005(6) 0.0036(6) C3 0.0586(9) 0.0492(9) 0.0346(7) 0.0001(6) 0.0043(6) 0.0120(7) C4 0.0511(9) 0.0541(9) 0.0340(7) 0.0058(6) 0.0047(6) 0.0086(7) C5 0.0370(7) 0.0435(8) 0.0373(7) 0.0052(6) -0.0001(5) 0.0026(6) C6 0.0494(9) 0.0483(9) 0.0466(8) 0.0124(7) 0.0032(7) 0.0030(7) C7 0.0586(10) 0.0407(9) 0.0613(10) 0.0101(7) 0.0030(8) 0.0041(7) C8 0.0589(10) 0.0393(9) 0.0575(10) -0.0004(7) 0.0045(8) 0.0081(7) C9 0.0482(8) 0.0423(8) 0.0413(8) 0.0013(6) 0.0053(6) 0.0049(6) C10 0.0349(7) 0.0379(7) 0.0368(7) 0.0026(6) -0.0010(5) 0.0014(5) C11 0.0520(8) 0.0369(8) 0.0379(7) -0.0013(6) 0.0020(6) 0.0061(6) C12 0.0447(8) 0.0365(7) 0.0410(7) 0.0014(6) 0.0011(6) -0.0003(6) C13 0.0396(7) 0.0405(8) 0.0392(7) 0.0053(6) 0.0030(6) -0.0007(6) C14 0.0439(8) 0.0398(8) 0.0424(8) 0.0039(6) -0.0017(6) -0.0014(6) C15 0.0461(8) 0.0401(8) 0.0544(9) 0.0068(7) 0.0025(7) -0.0005(6) C16 0.0460(8) 0.0490(9) 0.0577(10) 0.0181(8) -0.0004(7) 0.0044(7) C17 0.0488(9) 0.0605(10) 0.0420(8) 0.0113(7) -0.0041(7) -0.0003(7) C18 0.0461(8) 0.0484(9) 0.0406(8) 0.0028(7) 0.0017(6) -0.0028(7) C19 0.0832(13) 0.0423(9) 0.0783(12) 0.0007(9) -0.0084(10) 0.0027(9) O1 0.0761(8) 0.0412(6) 0.0389(6) -0.0004(4) 0.0091(5) 0.0075(5) N1 0.0439(7) 0.0358(6) 0.0333(6) 0.0015(5) 0.0019(5) 0.0030(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C2 N1 1.3539(17) . ? C2 C11 1.399(2) . ? C2 C3 1.433(2) . ? C3 C4 1.343(2) . ? C4 C5 1.428(2) . ? C5 C6 1.401(2) . ? C5 C10 1.4059(19) . ? C6 C7 1.373(2) . ? C7 C8 1.396(2) . ? C8 C9 1.375(2) . ? C9 C10 1.399(2) . ? C10 N1 1.3779(17) . ? C11 C12 1.403(2) . ? C12 O1 1.2722(17) . ? C12 C13 1.4959(19) . ? C13 C14 1.391(2) . ? C13 C18 1.396(2) . ? C14 C15 1.392(2) . ? C15 C16 1.394(2) . ? C15 C19 1.503(2) . ? C16 C17 1.378(2) . ? C17 C18 1.383(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C2 C11 119.91(12) . . ? N1 C2 C3 117.10(13) . . ? C11 C2 C3 122.89(13) . . ? C4 C3 C2 121.15(14) . . ? C3 C4 C5 120.93(13) . . ? C6 C5 C10 118.65(13) . . ? C6 C5 C4 123.79(13) . . ? C10 C5 C4 117.56(13) . . ? C7 C6 C5 120.79(14) . . ? C6 C7 C8 120.01(15) . . ? C9 C8 C7 120.55(15) . . ? C8 C9 C10 119.73(14) . . ? N1 C10 C9 120.30(12) . . ? N1 C10 C5 119.49(12) . . ? C9 C10 C5 120.18(13) . . ? C2 C11 C12 122.94(13) . . ? O1 C12 C11 122.98(13) . . ? O1 C12 C13 117.86(12) . . ? C11 C12 C13 119.05(13) . . ? C14 C13 C18 119.12(13) . . ? C14 C13 C12 122.60(12) . . ? C18 C13 C12 118.27(13) . . ? C13 C14 C15 121.61(14) . . ? C14 C15 C16 117.89(15) . . ? C14 C15 C19 121.11(14) . . ? C16 C15 C19 121.00(15) . . ? C17 C16 C15 121.18(15) . . ? C16 C17 C18 120.41(15) . . ? C17 C18 C13 119.76(15) . . ? C2 N1 C10 123.49(12) . . ? 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 N1 C2 C3 C4 5.2(2) . . . . ? C11 C2 C3 C4 -171.18(15) . . . . ? C2 C3 C4 C5 -1.2(2) . . . . ? C3 C4 C5 C6 175.68(15) . . . . ? C3 C4 C5 C10 -3.2(2) . . . . ? C10 C5 C6 C7 -0.3(2) . . . . ? C4 C5 C6 C7 -179.15(15) . . . . ? C5 C6 C7 C8 -1.8(3) . . . . ? C6 C7 C8 C9 1.3(3) . . . . ? C7 C8 C9 C10 1.2(3) . . . . ? C8 C9 C10 N1 174.76(14) . . . . ? C8 C9 C10 C5 -3.2(2) . . . . ? C6 C5 C10 N1 -175.25(13) . . . . ? C4 C5 C10 N1 3.7(2) . . . . ? C6 C5 C10 C9 2.7(2) . . . . ? C4 C5 C10 C9 -178.30(13) . . . . ? N1 C2 C11 C12 -6.2(2) . . . . ? C3 C2 C11 C12 170.03(15) . . . . ? C2 C11 C12 O1 5.4(2) . . . . ? C2 C11 C12 C13 -170.59(13) . . . . ? O1 C12 C13 C14 150.93(15) . . . . ? C11 C12 C13 C14 -32.8(2) . . . . ? O1 C12 C13 C18 -30.4(2) . . . . ? C11 C12 C13 C18 145.85(15) . . . . ? C18 C13 C14 C15 -0.8(2) . . . . ? C12 C13 C14 C15 177.92(13) . . . . ? C13 C14 C15 C16 -0.8(2) . . . . ? C13 C14 C15 C19 179.37(15) . . . . ? C14 C15 C16 C17 1.5(2) . . . . ? C19 C15 C16 C17 -178.75(16) . . . . ? C15 C16 C17 C18 -0.5(2) . . . . ? C16 C17 C18 C13 -1.2(2) . . . . ? C14 C13 C18 C17 1.8(2) . . . . ? C12 C13 C18 C17 -176.95(13) . . . . ? C11 C2 N1 C10 171.73(13) . . . . ? C3 C2 N1 C10 -4.7(2) . . . . ? C9 C10 N1 C2 -177.66(13) . . . . ? C5 C10 N1 C2 0.3(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O1 1.03(2) 1.72(2) 2.5998(15) 141.4(17) . _diffrn_measured_fraction_theta_max 0.965 _diffrn_reflns_theta_full 27.88 _diffrn_measured_fraction_theta_full 0.965 _refine_diff_density_max 0.222 _refine_diff_density_min -0.212 _refine_diff_density_rms 0.040 #===END data_compound7 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point '137-140' _chemical_formula_moiety ? _chemical_formula_sum 'C17 H12 F N O' _chemical_formula_weight 265.28 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' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 5.903(1) _cell_length_b 7.652(1) _cell_length_c 28.437(1) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1284.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173.0(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.372 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9765 _exptl_absorpt_correction_T_max 0.9952 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173.0(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1806 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0648 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 27.88 _reflns_number_total 1806 _reflns_number_gt 1211 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0515P)^2^+0.1707P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.8(17) _refine_ls_number_reflns 1806 _refine_ls_number_parameters 229 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0975 _refine_ls_R_factor_gt 0.0520 _refine_ls_wR_factor_ref 0.1157 _refine_ls_wR_factor_gt 0.0980 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1' C -0.1551(5) 0.0158(3) -0.20909(9) 0.0311(6) Uani 1 1 d . . . C2 C 0.2410(5) 0.0808(3) -0.10389(9) 0.0315(7) Uani 1 1 d . . . C2' C -0.3633(5) -0.0629(4) -0.21803(10) 0.0369(7) Uani 1 1 d . . . C3 C 0.4532(5) 0.1610(4) -0.09261(11) 0.0351(7) Uani 1 1 d . . . C3' C -0.4606(6) -0.0608(4) -0.26238(10) 0.0410(8) Uani 1 1 d . . . C4' C -0.3429(6) 0.0227(4) -0.29749(9) 0.0412(8) Uani 1 1 d . . . C4 C 0.5427(5) 0.1472(4) -0.04913(11) 0.0349(7) Uani 1 1 d . . . C4A C 0.4255(5) 0.0561(3) -0.01254(10) 0.0314(7) Uani 1 1 d . . . C5 C 0.5071(5) 0.0422(4) 0.03373(10) 0.0379(7) Uani 1 1 d . . . C5' C -0.1373(6) 0.1034(4) -0.29089(10) 0.0440(8) Uani 1 1 d . . . C6' C -0.0442(6) 0.0993(4) -0.24627(10) 0.0363(7) Uani 1 1 d . . . C6 C 0.3826(5) -0.0444(4) 0.06757(10) 0.0398(8) Uani 1 1 d . . . C7 C 0.1724(5) -0.1177(4) 0.05601(11) 0.0371(7) Uani 1 1 d . . . C8 C 0.0889(5) -0.1058(4) 0.01085(10) 0.0332(7) Uani 1 1 d . . . C8A C 0.2148(5) -0.0193(3) -0.02371(9) 0.0289(6) Uani 1 1 d . . . C9 C 0.1432(5) 0.0904(3) -0.14881(10) 0.0337(7) Uani 1 1 d . . . C10 C -0.0576(5) 0.0035(3) -0.16061(9) 0.0309(6) Uani 1 1 d . . . H1 H -0.017(6) -0.070(5) -0.0823(11) 0.072(11) Uiso 1 1 d . . . H2' H -0.438(5) -0.124(3) -0.1913(9) 0.037(8) Uiso 1 1 d . . . H3 H 0.536(5) 0.221(3) -0.1192(9) 0.037(8) Uiso 1 1 d . . . H3' H -0.600(5) -0.125(4) -0.2675(10) 0.045(9) Uiso 1 1 d . . . H4 H 0.692(5) 0.200(3) -0.0411(9) 0.041(8) Uiso 1 1 d . . . H5' H -0.056(5) 0.163(4) -0.3190(10) 0.050(9) Uiso 1 1 d . . . H5 H 0.658(6) 0.097(4) 0.0423(9) 0.046(8) Uiso 1 1 d . . . H6' H 0.100(5) 0.160(4) -0.2407(10) 0.051(9) Uiso 1 1 d . . . H6 H 0.430(5) -0.053(4) 0.1023(10) 0.045(8) Uiso 1 1 d . . . H7 H 0.085(5) -0.178(4) 0.0808(9) 0.036(8) Uiso 1 1 d . . . H8 H -0.062(5) -0.157(4) 0.0024(9) 0.043(9) Uiso 1 1 d . . . H9 H 0.230(4) 0.158(3) -0.1733(9) 0.037(8) Uiso 1 1 d . . . O11 O -0.1650(3) -0.0922(2) -0.13144(6) 0.0382(5) Uani 1 1 d . . . N1 N 0.1321(4) -0.0071(3) -0.06885(7) 0.0296(5) Uani 1 1 d . . . F12 F -0.4369(4) 0.0262(2) -0.34147(6) 0.0635(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1' 0.0366(16) 0.0245(13) 0.0322(16) -0.0001(11) 0.0008(13) 0.0022(13) C2 0.0331(16) 0.0280(13) 0.0334(16) -0.0001(12) 0.0042(13) 0.0003(13) C2' 0.0402(18) 0.0364(15) 0.0342(17) -0.0006(13) -0.0018(15) 0.0020(14) C3 0.0340(17) 0.0322(14) 0.0392(18) -0.0008(13) 0.0027(15) -0.0030(14) C3' 0.046(2) 0.0341(17) 0.0427(19) -0.0039(14) -0.0094(16) 0.0013(16) C4' 0.062(2) 0.0338(15) 0.0282(16) -0.0036(12) -0.0127(15) 0.0087(17) C4 0.0264(16) 0.0311(14) 0.0472(19) -0.0070(13) 0.0033(15) -0.0018(13) C4A 0.0308(16) 0.0262(13) 0.0373(16) -0.0030(12) -0.0048(13) 0.0021(13) C5 0.0345(18) 0.0343(15) 0.0448(18) -0.0074(14) -0.0077(15) 0.0032(14) C5' 0.069(2) 0.0337(15) 0.0297(17) 0.0025(13) -0.0013(17) -0.0043(17) C6' 0.047(2) 0.0314(15) 0.0304(17) 0.0032(12) 0.0012(15) -0.0029(15) C6 0.052(2) 0.0361(16) 0.0310(17) -0.0028(13) -0.0049(15) 0.0083(16) C7 0.0435(18) 0.0342(15) 0.0335(17) 0.0003(13) 0.0008(16) 0.0035(15) C8 0.0369(18) 0.0313(14) 0.0316(16) -0.0002(12) 0.0006(14) 0.0042(14) C8A 0.0330(16) 0.0283(13) 0.0254(15) -0.0027(11) -0.0009(12) 0.0046(13) C9 0.0382(17) 0.0332(14) 0.0296(16) 0.0026(12) 0.0042(14) -0.0030(14) C10 0.0343(16) 0.0283(13) 0.0302(15) 0.0002(12) 0.0047(13) 0.0048(14) O11 0.0398(11) 0.0425(10) 0.0323(11) 0.0043(8) 0.0014(9) -0.0099(10) N1 0.0316(13) 0.0289(11) 0.0283(13) -0.0026(9) 0.0007(10) -0.0001(11) F12 0.0943(16) 0.0558(11) 0.0405(11) 0.0014(9) -0.0259(11) -0.0012(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1' C2' 1.392(4) . ? C1' C6' 1.398(4) . ? C1' C10 1.497(3) . ? C2 N1 1.363(3) . ? C2 C9 1.404(4) . ? C2 C3 1.431(4) . ? C2' C3' 1.386(4) . ? C3 C4 1.348(4) . ? C3' C4' 1.374(4) . ? C4' F12 1.369(3) . ? C4' C5' 1.374(5) . ? C4 C4A 1.431(4) . ? C4A C5 1.405(4) . ? C4A C8A 1.408(4) . ? C5 C6 1.380(4) . ? C5' C6' 1.383(4) . ? C6 C7 1.401(4) . ? C7 C8 1.379(4) . ? C8 C8A 1.398(4) . ? C8A N1 1.377(3) . ? C9 C10 1.400(4) . ? C10 O11 1.275(3) . ? 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' C6' 118.2(3) . . ? C2' C1' C10 118.7(2) . . ? C6' C1' C10 123.0(3) . . ? N1 C2 C9 119.8(3) . . ? N1 C2 C3 117.4(3) . . ? C9 C2 C3 122.8(3) . . ? C3' C2' C1' 121.8(3) . . ? C4 C3 C2 121.0(3) . . ? C4' C3' C2' 117.2(3) . . ? F12 C4' C3' 117.9(3) . . ? F12 C4' C5' 118.3(3) . . ? C3' C4' C5' 123.8(3) . . ? C3 C4 C4A 121.0(3) . . ? C5 C4A C8A 118.9(3) . . ? C5 C4A C4 123.5(3) . . ? C8A C4A C4 117.6(2) . . ? C6 C5 C4A 120.5(3) . . ? C4' C5' C6' 117.8(3) . . ? C5' C6' C1' 121.2(3) . . ? C5 C6 C7 120.0(3) . . ? C8 C7 C6 120.6(3) . . ? C7 C8 C8A 119.7(3) . . ? N1 C8A C8 119.9(3) . . ? N1 C8A C4A 119.7(2) . . ? C8 C8A C4A 120.3(2) . . ? C10 C9 C2 122.8(3) . . ? O11 C10 C9 122.5(2) . . ? O11 C10 C1' 116.4(2) . . ? C9 C10 C1' 121.1(2) . . ? C2 N1 C8A 123.2(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 C6' C1' C2' C3' 0.3(4) . . . . ? C10 C1' C2' C3' -178.2(3) . . . . ? N1 C2 C3 C4 1.0(4) . . . . ? C9 C2 C3 C4 -179.3(3) . . . . ? C1' C2' C3' C4' 0.0(4) . . . . ? C2' C3' C4' F12 -179.9(2) . . . . ? C2' C3' C4' C5' -0.2(4) . . . . ? C2 C3 C4 C4A -1.7(4) . . . . ? C3 C4 C4A C5 -178.0(3) . . . . ? C3 C4 C4A C8A 0.4(4) . . . . ? C8A C4A C5 C6 0.1(4) . . . . ? C4 C4A C5 C6 178.5(2) . . . . ? F12 C4' C5' C6' 179.9(3) . . . . ? C3' C4' C5' C6' 0.2(4) . . . . ? C4' C5' C6' C1' 0.1(4) . . . . ? C2' C1' C6' C5' -0.3(4) . . . . ? C10 C1' C6' C5' 178.1(3) . . . . ? C4A C5 C6 C7 -0.6(4) . . . . ? C5 C6 C7 C8 0.6(4) . . . . ? C6 C7 C8 C8A -0.2(4) . . . . ? C7 C8 C8A N1 180.0(2) . . . . ? C7 C8 C8A C4A -0.3(4) . . . . ? C5 C4A C8A N1 -180.0(2) . . . . ? C4 C4A C8A N1 1.5(3) . . . . ? C5 C4A C8A C8 0.3(4) . . . . ? C4 C4A C8A C8 -178.2(2) . . . . ? N1 C2 C9 C10 -4.3(4) . . . . ? C3 C2 C9 C10 176.1(2) . . . . ? C2 C9 C10 O11 -0.7(4) . . . . ? C2 C9 C10 C1' -179.4(2) . . . . ? C2' C1' C10 O11 5.7(3) . . . . ? C6' C1' C10 O11 -172.7(2) . . . . ? C2' C1' C10 C9 -175.5(2) . . . . ? C6' C1' C10 C9 6.1(4) . . . . ? C9 C2 N1 C8A -178.6(2) . . . . ? C3 C2 N1 C8A 1.0(4) . . . . ? C8 C8A N1 C2 177.4(2) . . . . ? C4A C8A N1 C2 -2.3(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O11 1.07(3) 1.66(3) 2.582(3) 141(3) . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.88 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.180 _refine_diff_density_min -0.211 _refine_diff_density_rms 0.048 #===END data_compound11 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point '127-129' _chemical_formula_moiety ? _chemical_formula_sum 'C17 H12 Br N O' _chemical_formula_weight 326.19 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' 'O' 'O' 0.0106 0.0060 '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' 'Br' 'Br' -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P c 21 b' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, z+1/2' '-x, y+1/2, -z' 'x, y+1/2, -z+1/2' _cell_length_a 4.470(1) _cell_length_b 12.388(1) _cell_length_c 24.375(1) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1349.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173.0(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.605 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 3.039 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.3761 _exptl_absorpt_correction_T_max 0.4625 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1673 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0539 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 3.29 _diffrn_reflns_theta_max 27.89 _reflns_number_total 1673 _reflns_number_gt 1250 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0456P)^2^+1.5715P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.08(2) _refine_ls_number_reflns 1673 _refine_ls_number_parameters 225 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0769 _refine_ls_R_factor_gt 0.0453 _refine_ls_wR_factor_ref 0.1095 _refine_ls_wR_factor_gt 0.0934 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1' C -0.3028(13) -0.5691(5) -0.6067(3) 0.0313(14) Uani 1 1 d . . . C2 C -0.7765(13) -0.6562(5) -0.4842(3) 0.0285(13) Uani 1 1 d . . . C2' C -0.2846(16) -0.4790(5) -0.6407(3) 0.0330(14) Uani 1 1 d . . . C3 C -0.8656(15) -0.7527(5) -0.4556(3) 0.0331(15) Uani 1 1 d . . . C3' C -0.1107(15) -0.4813(6) -0.6868(3) 0.0368(15) Uani 1 1 d . . . C4 C -1.0661(14) -0.7481(5) -0.4145(3) 0.0333(14) Uani 1 1 d . . . H4 H -1.1236 -0.8129 -0.3965 0.040 Uiso 1 1 calc R . . C4' C 0.0498(14) -0.5726(7) -0.7020(3) 0.0409(16) Uani 1 1 d . . . C4A C -1.1956(14) -0.6474(5) -0.3970(3) 0.0294(14) Uani 1 1 d . . . C5' C 0.0380(17) -0.6623(7) -0.6684(3) 0.0459(18) Uani 1 1 d . . . C5 C -1.3959(15) -0.6389(5) -0.3540(3) 0.0358(15) Uani 1 1 d . . . C6 C -1.5116(15) -0.5388(6) -0.3391(3) 0.0371(16) Uani 1 1 d . . . C6' C -0.1380(14) -0.6616(5) -0.6210(3) 0.0330(15) Uani 1 1 d . . . C7 C -1.4202(16) -0.4467(6) -0.3668(3) 0.0380(15) Uani 1 1 d . . . C8 C -1.2187(16) -0.4534(5) -0.4100(3) 0.0353(15) Uani 1 1 d . . . C8A C -1.1039(13) -0.5543(5) -0.4248(3) 0.0278(13) Uani 1 1 d . . . C9 C -0.5730(14) -0.6573(5) -0.5277(3) 0.0315(14) Uani 1 1 d . . . C10 C -0.4989(14) -0.5630(5) -0.5568(3) 0.0308(13) Uani 1 1 d . . . O11 O -0.5957(10) -0.4708(3) -0.54407(19) 0.0368(11) Uani 1 1 d . . . N1 N -0.9016(12) -0.5628(4) -0.4670(2) 0.0286(11) Uani 1 1 d . . . Br1 Br -0.09172(16) -0.35906(10) -0.73232(2) 0.0514(2) Uani 1 1 d . . . H7 H -1.493(12) -0.384(5) -0.360(2) 0.015(16) Uiso 1 1 d . . . H6' H -0.155(14) -0.720(6) -0.601(3) 0.027(17) Uiso 1 1 d . . . H3 H -0.780(13) -0.814(5) -0.465(2) 0.018(15) Uiso 1 1 d . . . H8 H -1.159(12) -0.387(4) -0.428(2) 0.016(15) Uiso 1 1 d . . . H2' H -0.379(12) -0.419(5) -0.632(2) 0.012(14) Uiso 1 1 d . . . H6 H -1.647(16) -0.537(6) -0.307(3) 0.05(2) Uiso 1 1 d . . . H5' H 0.17(2) -0.730(8) -0.683(4) 0.07(3) Uiso 1 1 d . . . H5 H -1.476(16) -0.719(6) -0.334(3) 0.05(2) Uiso 1 1 d . . . H4' H 0.187(19) -0.566(8) -0.736(3) 0.07(3) Uiso 1 1 d . . . H9 H -0.461(14) -0.730(6) -0.540(3) 0.035(18) Uiso 1 1 d . . . H1 H -0.850(14) -0.508(6) -0.482(3) 0.021(17) 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 C1' 0.032(3) 0.028(3) 0.034(3) -0.003(3) -0.005(3) -0.008(3) C2 0.021(3) 0.022(3) 0.042(4) -0.002(2) -0.004(3) -0.002(3) C2' 0.035(3) 0.024(3) 0.040(4) -0.005(3) 0.004(3) -0.008(3) C3 0.038(4) 0.018(3) 0.043(4) 0.002(3) -0.007(3) 0.003(3) C3' 0.039(4) 0.039(4) 0.033(3) -0.006(3) -0.002(3) -0.005(3) C4 0.038(4) 0.024(3) 0.038(3) 0.008(3) -0.007(3) 0.001(3) C4' 0.032(4) 0.051(4) 0.039(4) -0.013(4) 0.000(3) -0.005(3) C4A 0.027(3) 0.029(3) 0.032(3) 0.003(3) -0.007(3) -0.006(3) C5' 0.044(4) 0.052(5) 0.042(4) -0.016(4) -0.009(3) 0.002(4) C5 0.039(4) 0.027(3) 0.041(4) 0.000(3) -0.006(3) -0.002(3) C6 0.032(3) 0.045(4) 0.035(4) -0.002(3) -0.002(3) -0.003(3) C6' 0.037(4) 0.026(3) 0.036(3) -0.002(3) -0.008(3) -0.002(3) C7 0.037(4) 0.034(4) 0.043(4) -0.005(3) -0.003(3) 0.003(3) C8 0.036(3) 0.029(3) 0.041(4) 0.001(3) -0.011(3) 0.002(3) C8A 0.024(3) 0.023(3) 0.036(3) 0.002(2) -0.007(3) 0.001(3) C9 0.033(3) 0.022(3) 0.039(3) 0.001(3) -0.004(3) 0.001(3) C10 0.031(3) 0.026(3) 0.036(3) -0.004(3) -0.004(3) -0.003(3) O11 0.043(3) 0.024(2) 0.044(3) 0.005(2) 0.006(2) -0.001(2) N1 0.027(2) 0.022(3) 0.037(3) 0.004(2) -0.005(2) -0.004(3) Br1 0.0718(5) 0.0438(3) 0.0386(3) 0.0015(4) 0.0118(3) -0.0117(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1' C2' 1.392(9) . ? C1' C6' 1.406(9) . ? C1' C10 1.500(9) . ? C2 N1 1.351(8) . ? C2 C9 1.397(9) . ? C2 C3 1.441(9) . ? C2' C3' 1.368(9) . ? C3 C4 1.346(10) . ? C3' C4' 1.389(10) . ? C3' Br1 1.879(7) . ? C4 C4A 1.439(9) . ? C4' C5' 1.382(11) . ? C4A C5 1.383(10) . ? C4A C8A 1.399(9) . ? C5' C6' 1.399(10) . ? C5 C6 1.391(10) . ? C6 C7 1.388(10) . ? C7 C8 1.387(10) . ? C8 C8A 1.398(9) . ? C8A N1 1.374(8) . ? C9 C10 1.407(9) . ? C10 O11 1.261(8) . ? 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' C6' 118.4(6) . . ? C2' C1' C10 118.4(6) . . ? C6' C1' C10 123.2(6) . . ? N1 C2 C9 120.9(6) . . ? N1 C2 C3 116.5(6) . . ? C9 C2 C3 122.6(6) . . ? C3' C2' C1' 120.4(7) . . ? C4 C3 C2 120.6(6) . . ? C2' C3' C4' 122.0(7) . . ? C2' C3' Br1 119.6(5) . . ? C4' C3' Br1 118.4(5) . . ? C3 C4 C4A 121.6(6) . . ? C5' C4' C3' 118.5(7) . . ? C5 C4A C8A 119.6(6) . . ? C5 C4A C4 123.4(6) . . ? C8A C4A C4 117.0(6) . . ? C4' C5' C6' 120.4(7) . . ? C4A C5 C6 120.4(6) . . ? C7 C6 C5 119.8(7) . . ? C5' C6' C1' 120.3(7) . . ? C8 C7 C6 120.7(7) . . ? C7 C8 C8A 119.2(6) . . ? N1 C8A C8 120.2(6) . . ? N1 C8A C4A 119.4(6) . . ? C8 C8A C4A 120.3(6) . . ? C2 C9 C10 121.9(6) . . ? O11 C10 C9 123.2(6) . . ? O11 C10 C1' 116.5(6) . . ? C9 C10 C1' 120.3(6) . . ? C2 N1 C8A 124.8(6) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6' C1' C2' C3' 0.2(9) . . . . ? C10 C1' C2' C3' -179.4(6) . . . . ? N1 C2 C3 C4 0.8(9) . . . . ? C9 C2 C3 C4 -179.0(6) . . . . ? C1' C2' C3' C4' 0.8(10) . . . . ? C1' C2' C3' Br1 179.6(5) . . . . ? C2 C3 C4 C4A -0.8(10) . . . . ? C2' C3' C4' C5' -1.7(10) . . . . ? Br1 C3' C4' C5' 179.5(5) . . . . ? C3 C4 C4A C5 -178.2(6) . . . . ? C3 C4 C4A C8A 0.0(9) . . . . ? C3' C4' C5' C6' 1.5(10) . . . . ? C8A C4A C5 C6 1.5(9) . . . . ? C4 C4A C5 C6 179.7(6) . . . . ? C4A C5 C6 C7 -1.5(10) . . . . ? C4' C5' C6' C1' -0.6(10) . . . . ? C2' C1' C6' C5' -0.3(9) . . . . ? C10 C1' C6' C5' 179.2(6) . . . . ? C5 C6 C7 C8 1.2(10) . . . . ? C6 C7 C8 C8A -1.0(10) . . . . ? C7 C8 C8A N1 -179.3(6) . . . . ? C7 C8 C8A C4A 1.1(9) . . . . ? C5 C4A C8A N1 179.1(5) . . . . ? C4 C4A C8A N1 0.8(8) . . . . ? C5 C4A C8A C8 -1.4(9) . . . . ? C4 C4A C8A C8 -179.6(6) . . . . ? N1 C2 C9 C10 -2.7(9) . . . . ? C3 C2 C9 C10 177.0(6) . . . . ? C2 C9 C10 O11 4.2(10) . . . . ? C2 C9 C10 C1' -174.0(6) . . . . ? C2' C1' C10 O11 -11.4(9) . . . . ? C6' C1' C10 O11 169.0(6) . . . . ? C2' C1' C10 C9 167.0(6) . . . . ? C6' C1' C10 C9 -12.6(9) . . . . ? C9 C2 N1 C8A 179.8(5) . . . . ? C3 C2 N1 C8A 0.1(8) . . . . ? C8 C8A N1 C2 179.6(6) . . . . ? C4A C8A N1 C2 -0.8(8) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O11 0.81(7) 1.94(7) 2.588(7) 137(6) . _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.89 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.397 _refine_diff_density_min -0.623 _refine_diff_density_rms 0.087 #===END