# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_1 _database_code_depnum_ccdc_archive 'CCDC 822932' #TrackingRef 'CIF-all.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H14 N2 O2' _chemical_melting_point ? _exptl_crystal_description Block _exptl_crystal_colour Red _diffrn_ambient_temperature 150(2) _chemical_formula_weight 290.32 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' _symmetry_int_tables_number 2 _chemical_absolute_configuration ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.7407(7) _cell_length_b 11.6842(8) _cell_length_c 14.5889(9) _cell_angle_alpha 102.850(6) _cell_angle_beta 104.501(6) _cell_angle_gamma 104.832(6) _cell_volume 1479.34(17) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5237 _cell_measurement_theta_min 0.976 _cell_measurement_theta_max 0.982 _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.303 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_radiation_probe ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OXFORD DIFFRACTION XCALIBUR-S' _diffrn_measurement_method \w/q-scan _diffrn_detector_area_resol_mean 15.9948 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% <3%> _diffrn_reflns_number 10768 _diffrn_reflns_av_R_equivalents 0.0426 _diffrn_reflns_av_sigmaI/netI 0.1228 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.42 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5237 _reflns_number_gt 2606 _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^)+(0.0633P)^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 none _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5223 _refine_ls_number_parameters 397 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1018 _refine_ls_R_factor_gt 0.0471 _refine_ls_wR_factor_ref 0.1261 _refine_ls_wR_factor_gt 0.1173 _refine_ls_goodness_of_fit_ref 0.815 _refine_ls_restrained_S_all 0.815 _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 O1 O 0.3928(2) 0.15870(17) 0.15079(14) 0.0339(5) Uani 1 1 d . . . O2 O 0.4688(2) 0.43321(16) 0.40423(14) 0.0296(5) Uani 1 1 d . . . O3 O 1.0194(2) 0.20714(19) 0.14643(16) 0.0407(6) Uani 1 1 d . . . O4 O 0.8005(2) 0.43507(17) 0.05524(14) 0.0332(5) Uani 1 1 d . . . N1 N 0.6708(2) 0.3618(2) 0.54723(17) 0.0296(6) Uani 1 1 d . . . H1 H 0.6318 0.4207 0.5403 0.035 Uiso 1 1 calc R . . N2 N 0.3253(3) 0.3035(2) 0.52503(17) 0.0272(6) Uani 1 1 d . . . H2 H 0.3933 0.3769 0.5403 0.033 Uiso 1 1 calc R . . N3 N 0.6405(3) 0.2049(2) -0.24369(18) 0.0345(7) Uani 1 1 d . . . H3 H 0.6895 0.2355 -0.2807 0.041 Uiso 1 1 calc R . . N4 N 1.0883(2) 0.3036(2) -0.15655(17) 0.0260(6) Uani 1 1 d . . . H4 H 1.1204 0.3852 -0.1326 0.031 Uiso 1 1 calc R . . C1 C 0.3988(3) 0.2761(3) 0.1467(2) 0.0278(7) Uani 1 1 d . . . C2 C 0.3805(3) 0.2930(3) 0.0529(2) 0.0322(8) Uani 1 1 d . . . H2A H 0.3649 0.2267 -0.0039 0.039 Uiso 1 1 calc R . . C3 C 0.3860(3) 0.4091(3) 0.0466(2) 0.0333(8) Uani 1 1 d . . . H3A H 0.3745 0.4231 -0.0162 0.040 Uiso 1 1 calc R . . C4 C 0.4079(3) 0.5072(3) 0.1286(2) 0.0329(8) Uani 1 1 d . . . H4A H 0.4109 0.5867 0.1217 0.040 Uiso 1 1 calc R . . C5 C 0.4252(3) 0.4883(3) 0.2198(2) 0.0311(8) Uani 1 1 d . . . H5 H 0.4403 0.5551 0.2762 0.037 Uiso 1 1 calc R . . C6 C 0.4207(3) 0.3710(2) 0.2304(2) 0.0226(7) Uani 1 1 d . . . C7 C 0.4418(3) 0.3484(2) 0.3268(2) 0.0222(7) Uani 1 1 d . . . C8 C 0.4314(3) 0.2231(2) 0.3258(2) 0.0218(7) Uani 1 1 d . . . C9 C 0.4101(3) 0.1386(3) 0.2405(2) 0.0287(7) Uani 1 1 d . . . H9 H 0.4068 0.0574 0.2428 0.034 Uiso 1 1 calc R . . C10 C 0.4463(3) 0.1838(2) 0.4196(2) 0.0224(7) Uani 1 1 d . . . H10 H 0.4287 0.0925 0.3965 0.027 Uiso 1 1 calc R . . C11 C 0.6030(3) 0.2384(2) 0.4950(2) 0.0240(7) Uani 1 1 d . . . C12 C 0.6997(3) 0.1786(3) 0.5273(2) 0.0316(8) Uani 1 1 d . . . H12 H 0.6823 0.0918 0.5041 0.038 Uiso 1 1 calc R . . C13 C 0.8295(3) 0.2672(3) 0.6011(2) 0.0368(8) Uani 1 1 d . . . H13 H 0.9152 0.2514 0.6363 0.044 Uiso 1 1 calc R . . C14 C 0.8091(3) 0.3797(3) 0.6123(2) 0.0348(8) Uani 1 1 d . . . H14 H 0.8783 0.4570 0.6572 0.042 Uiso 1 1 calc R . . C15 C 0.3249(3) 0.1950(2) 0.46497(19) 0.0203(6) Uani 1 1 d . . . C16 C 0.2013(3) 0.1036(3) 0.4598(2) 0.0262(7) Uani 1 1 d . . . H16 H 0.1712 0.0183 0.4230 0.031 Uiso 1 1 calc R . . C17 C 0.1258(3) 0.1576(3) 0.5185(2) 0.0307(7) Uani 1 1 d . . . H17 H 0.0363 0.1156 0.5289 0.037 Uiso 1 1 calc R . . C18 C 0.2050(3) 0.2807(3) 0.5574(2) 0.0300(7) Uani 1 1 d . . . H18 H 0.1805 0.3408 0.6001 0.036 Uiso 1 1 calc R . . C19 C 0.9559(3) 0.2667(3) 0.2085(2) 0.0317(8) Uani 1 1 d . . . C20 C 0.9796(4) 0.2502(3) 0.3020(2) 0.0419(9) Uani 1 1 d . . . H20 H 1.0404 0.2026 0.3226 0.050 Uiso 1 1 calc R . . C21 C 0.9129(3) 0.3042(3) 0.3639(3) 0.0422(9) Uani 1 1 d . . . H21 H 0.9255 0.2920 0.4273 0.051 Uiso 1 1 calc R . . C22 C 0.8271(3) 0.3766(3) 0.3351(2) 0.0386(8) Uani 1 1 d . . . H22 H 0.7813 0.4132 0.3785 0.046 Uiso 1 1 calc R . . C23 C 0.8089(3) 0.3949(3) 0.2439(2) 0.0324(8) Uani 1 1 d . . . H23 H 0.7511 0.4452 0.2248 0.039 Uiso 1 1 calc R . . C24 C 0.8740(3) 0.3407(2) 0.1785(2) 0.0267(7) Uani 1 1 d . . . C25 C 0.8560(3) 0.3581(2) 0.0804(2) 0.0257(7) Uani 1 1 d . . . C26 C 0.9077(3) 0.2790(2) 0.0150(2) 0.0247(7) Uani 1 1 d . . . C27 C 0.9871(3) 0.2123(3) 0.0517(2) 0.0360(8) Uani 1 1 d . . . H27 H 1.0240 0.1647 0.0081 0.043 Uiso 1 1 calc R . . C28 C 0.8710(3) 0.2777(3) -0.0929(2) 0.0272(7) Uani 1 1 d . . . H28 H 0.8910 0.3662 -0.0925 0.033 Uiso 1 1 calc R . . C29 C 0.7046(3) 0.2107(2) -0.1468(2) 0.0263(7) Uani 1 1 d . . . C30 C 0.5920(3) 0.1536(2) -0.1164(2) 0.0291(7) Uani 1 1 d . . . H30 H 0.6028 0.1437 -0.0524 0.035 Uiso 1 1 calc R . . C31 C 0.4560(3) 0.1115(3) -0.1964(3) 0.0372(8) Uani 1 1 d . . . H31 H 0.3592 0.0683 -0.1962 0.045 Uiso 1 1 calc R . . C32 C 0.4901(3) 0.1446(3) -0.2738(3) 0.0399(9) Uani 1 1 d . . . H32 H 0.4208 0.1285 -0.3378 0.048 Uiso 1 1 calc R . . C33 C 0.9646(3) 0.2265(3) -0.1475(2) 0.0264(7) Uani 1 1 d . . . C34 C 0.9532(3) 0.1080(3) -0.1947(2) 0.0374(8) Uani 1 1 d . . . H34 H 0.8775 0.0342 -0.2009 0.045 Uiso 1 1 calc R . . C35 C 1.0733(3) 0.1144(3) -0.2325(2) 0.0373(9) Uani 1 1 d . . . H35 H 1.0933 0.0458 -0.2686 0.045 Uiso 1 1 calc R . . C36 C 1.1552(3) 0.2359(3) -0.2080(2) 0.0326(8) Uani 1 1 d . . . H36 H 1.2432 0.2681 -0.2239 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 O1 0.0492(13) 0.0298(12) 0.0213(12) 0.0056(10) 0.0105(10) 0.0137(10) O2 0.0438(12) 0.0227(11) 0.0202(12) 0.0044(10) 0.0088(9) 0.0111(9) O3 0.0474(14) 0.0507(14) 0.0334(14) 0.0199(12) 0.0085(11) 0.0301(11) O4 0.0407(12) 0.0335(12) 0.0289(12) 0.0106(10) 0.0094(10) 0.0193(10) N1 0.0287(13) 0.0300(14) 0.0296(15) 0.0118(12) 0.0040(12) 0.0119(11) N2 0.0311(14) 0.0229(13) 0.0267(15) 0.0101(12) 0.0085(11) 0.0061(10) N3 0.0332(15) 0.0413(15) 0.0299(16) 0.0127(13) 0.0083(12) 0.0147(12) N4 0.0243(13) 0.0315(14) 0.0215(14) 0.0086(12) 0.0044(11) 0.0106(11) C1 0.0267(16) 0.0277(17) 0.0273(18) 0.0072(15) 0.0082(13) 0.0075(13) C2 0.0317(17) 0.0409(19) 0.0210(17) 0.0061(15) 0.0070(13) 0.0113(14) C3 0.0309(17) 0.046(2) 0.0258(19) 0.0187(17) 0.0066(14) 0.0125(15) C4 0.0380(18) 0.0353(18) 0.0279(19) 0.0161(16) 0.0057(14) 0.0156(14) C5 0.0370(17) 0.0323(17) 0.0253(18) 0.0109(15) 0.0079(14) 0.0137(14) C6 0.0228(14) 0.0254(15) 0.0193(16) 0.0079(14) 0.0036(12) 0.0099(12) C7 0.0205(14) 0.0227(15) 0.0206(17) 0.0046(14) 0.0056(12) 0.0056(12) C8 0.0210(14) 0.0237(15) 0.0183(16) 0.0064(14) 0.0035(12) 0.0064(12) C9 0.0328(17) 0.0268(16) 0.0291(19) 0.0126(15) 0.0102(14) 0.0104(13) C10 0.0285(15) 0.0185(14) 0.0213(16) 0.0083(13) 0.0058(13) 0.0096(12) C11 0.0266(15) 0.0287(16) 0.0213(16) 0.0132(14) 0.0080(13) 0.0119(13) C12 0.0356(17) 0.0357(18) 0.0307(18) 0.0137(16) 0.0120(15) 0.0193(14) C13 0.0280(17) 0.055(2) 0.0299(19) 0.0147(17) 0.0055(14) 0.0208(16) C14 0.0234(16) 0.044(2) 0.0282(19) 0.0082(16) 0.0036(14) 0.0043(14) C15 0.0275(15) 0.0216(15) 0.0115(15) 0.0080(13) 0.0001(12) 0.0112(12) C16 0.0290(16) 0.0218(15) 0.0250(18) 0.0088(14) 0.0020(13) 0.0088(13) C17 0.0326(17) 0.0326(18) 0.0332(19) 0.0182(15) 0.0133(14) 0.0116(14) C18 0.0358(17) 0.0341(18) 0.0279(18) 0.0141(15) 0.0145(15) 0.0159(14) C19 0.0333(17) 0.0354(18) 0.0269(19) 0.0130(16) 0.0045(14) 0.0142(15) C20 0.043(2) 0.046(2) 0.040(2) 0.0229(18) 0.0067(17) 0.0173(16) C21 0.0429(19) 0.056(2) 0.032(2) 0.0274(18) 0.0118(16) 0.0111(17) C22 0.0342(18) 0.053(2) 0.031(2) 0.0162(17) 0.0125(15) 0.0119(16) C23 0.0289(16) 0.0377(18) 0.0284(19) 0.0110(16) 0.0059(14) 0.0099(14) C24 0.0238(15) 0.0282(16) 0.0242(17) 0.0091(14) 0.0025(13) 0.0063(13) C25 0.0232(15) 0.0245(16) 0.0244(17) 0.0077(14) 0.0010(13) 0.0059(13) C26 0.0228(15) 0.0263(16) 0.0239(17) 0.0091(14) 0.0031(13) 0.0095(13) C27 0.0372(18) 0.0445(19) 0.0296(19) 0.0132(16) 0.0081(15) 0.0201(15) C28 0.0280(16) 0.0264(16) 0.0269(18) 0.0075(14) 0.0072(13) 0.0108(13) C29 0.0257(16) 0.0288(16) 0.0239(17) 0.0065(14) 0.0048(13) 0.0130(13) C30 0.0281(16) 0.0331(17) 0.0279(18) 0.0094(15) 0.0094(14) 0.0127(14) C31 0.0245(16) 0.0347(18) 0.045(2) 0.0040(17) 0.0078(15) 0.0092(14) C32 0.0291(18) 0.045(2) 0.038(2) 0.0030(17) 0.0021(16) 0.0172(15) C33 0.0230(15) 0.0327(17) 0.0193(16) 0.0063(14) 0.0023(13) 0.0085(13) C34 0.0277(17) 0.0331(18) 0.041(2) -0.0002(16) 0.0070(15) 0.0062(14) C35 0.0274(17) 0.041(2) 0.035(2) -0.0014(17) 0.0040(15) 0.0137(15) C36 0.0237(16) 0.046(2) 0.0244(18) 0.0060(16) 0.0049(14) 0.0124(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C9 1.357(3) . ? O1 C1 1.374(3) . ? O2 C7 1.244(3) . ? O3 C27 1.358(4) . ? O3 C19 1.381(3) . ? O4 C25 1.238(3) . ? N1 C11 1.366(3) . ? N1 C14 1.374(3) . ? N1 H1 0.8800 . ? N2 C18 1.357(4) . ? N2 C15 1.370(3) . ? N2 H2 0.8800 . ? N3 C32 1.359(4) . ? N3 C29 1.374(3) . ? N3 H3 0.8800 . ? N4 C33 1.363(3) . ? N4 C36 1.363(3) . ? N4 H4 0.8800 . ? C1 C6 1.382(4) . ? C1 C2 1.400(4) . ? C2 C3 1.368(4) . ? C2 H2A 0.9500 . ? C3 C4 1.390(4) . ? C3 H3A 0.9500 . ? C4 C5 1.373(4) . ? C4 H4A 0.9500 . ? C5 C6 1.405(4) . ? C5 H5 0.9500 . ? C6 C7 1.463(4) . ? C7 C8 1.438(4) . ? C8 C9 1.337(4) . ? C8 C10 1.523(4) . ? C9 H9 0.9500 . ? C10 C15 1.511(4) . ? C10 C11 1.515(4) . ? C10 H10 1.0000 . ? C11 C12 1.363(4) . ? C12 C13 1.408(4) . ? C12 H12 0.9500 . ? C13 C14 1.359(4) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C16 1.362(4) . ? C16 C17 1.409(4) . ? C16 H16 0.9500 . ? C17 C18 1.355(4) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 C24 1.387(4) . ? C19 C20 1.391(4) . ? C20 C21 1.373(4) . ? C20 H20 0.9500 . ? C21 C22 1.391(4) . ? C21 H21 0.9500 . ? C22 C23 1.369(4) . ? C22 H22 0.9500 . ? C23 C24 1.398(4) . ? C23 H23 0.9500 . ? C24 C25 1.463(4) . ? C25 C26 1.451(4) . ? C26 C27 1.334(4) . ? C26 C28 1.519(4) . ? C27 H27 0.9500 . ? C28 C33 1.501(4) . ? C28 C29 1.516(4) . ? C28 H28 1.0000 . ? C29 C30 1.358(4) . ? C30 C31 1.413(4) . ? C30 H30 0.9500 . ? C31 C32 1.361(5) . ? C31 H31 0.9500 . ? C32 H32 0.9500 . ? C33 C34 1.365(4) . ? C34 C35 1.404(4) . ? C34 H34 0.9500 . ? C35 C36 1.354(4) . ? C35 H35 0.9500 . ? C36 H36 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 C9 O1 C1 117.6(2) . . ? C27 O3 C19 118.4(2) . . ? C11 N1 C14 109.6(2) . . ? C11 N1 H1 125.2 . . ? C14 N1 H1 125.2 . . ? C18 N2 C15 109.8(2) . . ? C18 N2 H2 125.1 . . ? C15 N2 H2 125.1 . . ? C32 N3 C29 109.7(3) . . ? C32 N3 H3 125.1 . . ? C29 N3 H3 125.1 . . ? C33 N4 C36 110.2(2) . . ? C33 N4 H4 124.9 . . ? C36 N4 H4 124.9 . . ? O1 C1 C6 121.7(3) . . ? O1 C1 C2 115.9(3) . . ? C6 C1 C2 122.5(3) . . ? C3 C2 C1 117.2(3) . . ? C3 C2 H2A 121.4 . . ? C1 C2 H2A 121.4 . . ? C2 C3 C4 122.3(3) . . ? C2 C3 H3A 118.8 . . ? C4 C3 H3A 118.8 . . ? C5 C4 C3 119.4(3) . . ? C5 C4 H4A 120.3 . . ? C3 C4 H4A 120.3 . . ? C4 C5 C6 120.5(3) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C1 C6 C5 118.1(3) . . ? C1 C6 C7 120.0(3) . . ? C5 C6 C7 121.8(3) . . ? O2 C7 C8 122.9(3) . . ? O2 C7 C6 121.6(3) . . ? C8 C7 C6 115.6(2) . . ? C9 C8 C7 119.3(3) . . ? C9 C8 C10 118.8(2) . . ? C7 C8 C10 121.9(2) . . ? C8 C9 O1 125.7(3) . . ? C8 C9 H9 117.1 . . ? O1 C9 H9 117.1 . . ? C15 C10 C11 113.3(2) . . ? C15 C10 C8 114.1(2) . . ? C11 C10 C8 114.2(2) . . ? C15 C10 H10 104.6 . . ? C11 C10 H10 104.6 . . ? C8 C10 H10 104.6 . . ? C12 C11 N1 107.1(2) . . ? C12 C11 C10 128.8(2) . . ? N1 C11 C10 124.1(2) . . ? C11 C12 C13 108.4(3) . . ? C11 C12 H12 125.8 . . ? C13 C12 H12 125.8 . . ? C14 C13 C12 107.1(3) . . ? C14 C13 H13 126.4 . . ? C12 C13 H13 126.4 . . ? C13 C14 N1 107.8(3) . . ? C13 C14 H14 126.1 . . ? N1 C14 H14 126.1 . . ? C16 C15 N2 106.8(3) . . ? C16 C15 C10 128.7(3) . . ? N2 C15 C10 124.4(2) . . ? C15 C16 C17 108.2(2) . . ? C15 C16 H16 125.9 . . ? C17 C16 H16 125.9 . . ? C18 C17 C16 107.0(3) . . ? C18 C17 H17 126.5 . . ? C16 C17 H17 126.5 . . ? C17 C18 N2 108.3(3) . . ? C17 C18 H18 125.9 . . ? N2 C18 H18 125.9 . . ? O3 C19 C24 120.9(3) . . ? O3 C19 C20 117.0(3) . . ? C24 C19 C20 122.0(3) . . ? C21 C20 C19 118.3(3) . . ? C21 C20 H20 120.8 . . ? C19 C20 H20 120.8 . . ? C20 C21 C22 121.0(3) . . ? C20 C21 H21 119.5 . . ? C22 C21 H21 119.5 . . ? C23 C22 C21 119.8(3) . . ? C23 C22 H22 120.1 . . ? C21 C22 H22 120.1 . . ? C22 C23 C24 121.0(3) . . ? C22 C23 H23 119.5 . . ? C24 C23 H23 119.5 . . ? C19 C24 C23 117.8(3) . . ? C19 C24 C25 119.9(3) . . ? C23 C24 C25 122.2(3) . . ? O4 C25 C26 122.4(3) . . ? O4 C25 C24 122.2(3) . . ? C26 C25 C24 115.4(2) . . ? C27 C26 C25 119.2(3) . . ? C27 C26 C28 122.6(3) . . ? C25 C26 C28 118.1(2) . . ? C26 C27 O3 125.1(3) . . ? C26 C27 H27 117.4 . . ? O3 C27 H27 117.4 . . ? C33 C28 C29 111.5(2) . . ? C33 C28 C26 114.9(2) . . ? C29 C28 C26 109.4(2) . . ? C33 C28 H28 106.8 . . ? C29 C28 H28 106.8 . . ? C26 C28 H28 106.8 . . ? C30 C29 N3 107.0(2) . . ? C30 C29 C28 132.1(3) . . ? N3 C29 C28 120.9(3) . . ? C29 C30 C31 108.3(3) . . ? C29 C30 H30 125.9 . . ? C31 C30 H30 125.9 . . ? C32 C31 C30 106.9(3) . . ? C32 C31 H31 126.5 . . ? C30 C31 H31 126.5 . . ? N3 C32 C31 108.1(3) . . ? N3 C32 H32 126.0 . . ? C31 C32 H32 126.0 . . ? N4 C33 C34 106.7(3) . . ? N4 C33 C28 120.9(2) . . ? C34 C33 C28 132.4(3) . . ? C33 C34 C35 108.0(3) . . ? C33 C34 H34 126.0 . . ? C35 C34 H34 126.0 . . ? C36 C35 C34 107.6(3) . . ? C36 C35 H35 126.2 . . ? C34 C35 H35 126.2 . . ? C35 C36 N4 107.5(3) . . ? C35 C36 H36 126.3 . . ? N4 C36 H36 126.3 . . ? 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 C9 O1 C1 C6 -0.4(4) . . . . ? C9 O1 C1 C2 180.0(2) . . . . ? O1 C1 C2 C3 -179.9(2) . . . . ? C6 C1 C2 C3 0.4(4) . . . . ? C1 C2 C3 C4 -0.4(4) . . . . ? C2 C3 C4 C5 0.2(4) . . . . ? C3 C4 C5 C6 0.0(4) . . . . ? O1 C1 C6 C5 -179.9(2) . . . . ? C2 C1 C6 C5 -0.2(4) . . . . ? O1 C1 C6 C7 1.4(4) . . . . ? C2 C1 C6 C7 -178.9(3) . . . . ? C4 C5 C6 C1 0.1(4) . . . . ? C4 C5 C6 C7 178.7(3) . . . . ? C1 C6 C7 O2 176.6(3) . . . . ? C5 C6 C7 O2 -2.1(4) . . . . ? C1 C6 C7 C8 -2.5(4) . . . . ? C5 C6 C7 C8 178.9(3) . . . . ? O2 C7 C8 C9 -176.4(3) . . . . ? C6 C7 C8 C9 2.7(4) . . . . ? O2 C7 C8 C10 2.7(4) . . . . ? C6 C7 C8 C10 -178.2(2) . . . . ? C7 C8 C9 O1 -1.9(4) . . . . ? C10 C8 C9 O1 179.0(2) . . . . ? C1 O1 C9 C8 0.6(4) . . . . ? C9 C8 C10 C15 -117.8(3) . . . . ? C7 C8 C10 C15 63.1(3) . . . . ? C9 C8 C10 C11 109.7(3) . . . . ? C7 C8 C10 C11 -69.4(3) . . . . ? C14 N1 C11 C12 -0.1(3) . . . . ? C14 N1 C11 C10 177.3(3) . . . . ? C15 C10 C11 C12 111.9(3) . . . . ? C8 C10 C11 C12 -115.2(3) . . . . ? C15 C10 C11 N1 -64.9(4) . . . . ? C8 C10 C11 N1 67.9(4) . . . . ? N1 C11 C12 C13 0.0(4) . . . . ? C10 C11 C12 C13 -177.3(3) . . . . ? C11 C12 C13 C14 0.1(4) . . . . ? C12 C13 C14 N1 -0.2(4) . . . . ? C11 N1 C14 C13 0.2(4) . . . . ? C18 N2 C15 C16 0.3(3) . . . . ? C18 N2 C15 C10 -176.8(2) . . . . ? C11 C10 C15 C16 -124.9(3) . . . . ? C8 C10 C15 C16 102.2(3) . . . . ? C11 C10 C15 N2 51.7(3) . . . . ? C8 C10 C15 N2 -81.2(3) . . . . ? N2 C15 C16 C17 -0.5(3) . . . . ? C10 C15 C16 C17 176.6(3) . . . . ? C15 C16 C17 C18 0.4(3) . . . . ? C16 C17 C18 N2 -0.2(3) . . . . ? C15 N2 C18 C17 -0.1(3) . . . . ? C27 O3 C19 C24 -6.6(4) . . . . ? C27 O3 C19 C20 174.2(3) . . . . ? O3 C19 C20 C21 -177.4(3) . . . . ? C24 C19 C20 C21 3.3(5) . . . . ? C19 C20 C21 C22 -1.7(5) . . . . ? C20 C21 C22 C23 -0.2(5) . . . . ? C21 C22 C23 C24 0.7(4) . . . . ? O3 C19 C24 C23 178.0(2) . . . . ? C20 C19 C24 C23 -2.8(4) . . . . ? O3 C19 C24 C25 -1.0(4) . . . . ? C20 C19 C24 C25 178.2(3) . . . . ? C22 C23 C24 C19 0.8(4) . . . . ? C22 C23 C24 C25 179.7(3) . . . . ? C19 C24 C25 O4 -170.7(2) . . . . ? C23 C24 C25 O4 10.4(4) . . . . ? C19 C24 C25 C26 9.2(4) . . . . ? C23 C24 C25 C26 -169.7(2) . . . . ? O4 C25 C26 C27 169.7(3) . . . . ? C24 C25 C26 C27 -10.3(4) . . . . ? O4 C25 C26 C28 -9.2(4) . . . . ? C24 C25 C26 C28 170.8(2) . . . . ? C25 C26 C27 O3 3.2(4) . . . . ? C28 C26 C27 O3 -178.0(3) . . . . ? C19 O3 C27 C26 5.6(4) . . . . ? C27 C26 C28 C33 -16.6(4) . . . . ? C25 C26 C28 C33 162.3(2) . . . . ? C27 C26 C28 C29 109.8(3) . . . . ? C25 C26 C28 C29 -71.3(3) . . . . ? C32 N3 C29 C30 -0.2(3) . . . . ? C32 N3 C29 C28 -177.6(2) . . . . ? C33 C28 C29 C30 126.8(3) . . . . ? C26 C28 C29 C30 -1.5(4) . . . . ? C33 C28 C29 N3 -56.6(3) . . . . ? C26 C28 C29 N3 175.1(2) . . . . ? N3 C29 C30 C31 0.2(3) . . . . ? C28 C29 C30 C31 177.1(3) . . . . ? C29 C30 C31 C32 -0.1(3) . . . . ? C29 N3 C32 C31 0.2(3) . . . . ? C30 C31 C32 N3 -0.1(3) . . . . ? C36 N4 C33 C34 -0.2(3) . . . . ? C36 N4 C33 C28 179.4(2) . . . . ? C29 C28 C33 N4 138.4(3) . . . . ? C26 C28 C33 N4 -96.4(3) . . . . ? C29 C28 C33 C34 -42.1(4) . . . . ? C26 C28 C33 C34 83.2(4) . . . . ? N4 C33 C34 C35 0.2(3) . . . . ? C28 C33 C34 C35 -179.4(3) . . . . ? C33 C34 C35 C36 -0.1(3) . . . . ? C34 C35 C36 N4 0.0(3) . . . . ? C33 N4 C36 C35 0.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.305 _refine_diff_density_min -0.244 _refine_diff_density_rms 0.072 data_2 _database_code_depnum_ccdc_archive 'CCDC 822933' #TrackingRef 'CIF-all.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H16 N2 O2' _chemical_melting_point ? _exptl_crystal_description block _exptl_crystal_colour yellow _diffrn_ambient_temperature 293(2) _chemical_formula_weight 304.34 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 'P 21/c' _symmetry_int_tables_number 14 _chemical_absolute_configuration ? 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 15.688(5) _cell_length_b 22.176(5) _cell_length_c 8.850(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 103.392(5) _cell_angle_gamma 90.000(5) _cell_volume 2995(2) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 10922 _cell_measurement_theta_min 0.980 _cell_measurement_theta_max 0.984 _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.350 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1280 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_radiation_probe ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 54239 _diffrn_reflns_av_R_equivalents 0.0413 _diffrn_reflns_av_sigmaI/netI 0.0362 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -33 _diffrn_reflns_limit_k_max 33 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.33 _diffrn_reflns_theta_max 32.58 _reflns_number_total 10922 _reflns_number_gt 7863 _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^)+(0.1337P)^2^+2.5304P] 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 riding _refine_ls_extinction_method SHELXL _refine_ls_number_reflns 10779 _refine_ls_number_parameters 416 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0941 _refine_ls_R_factor_gt 0.0676 _refine_ls_wR_factor_ref 0.2389 _refine_ls_wR_factor_gt 0.2065 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _refine_ls_shift/su_max 0.051 _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 O4 O 0.16716(8) 0.65501(6) 0.90362(15) 0.0189(2) Uani 1 1 d . . . O3 O 0.24937(8) 0.51507(6) 1.20543(16) 0.0209(3) Uani 1 1 d . . . C26 C 0.19063(10) 0.61108(7) 0.98916(18) 0.0148(3) Uani 1 1 d . . . C25 C 0.28241(10) 0.59078(7) 1.03062(19) 0.0155(3) Uani 1 1 d . . . N3 N -0.08437(9) 0.60709(7) 0.78126(18) 0.0193(3) Uani 1 1 d . . . H3A H -0.1148 0.6288 0.8300 0.023 Uiso 1 1 calc R . . C27 C 0.13141(10) 0.57506(7) 1.05831(19) 0.0151(3) Uani 1 1 d . . . N4 N 0.03190(10) 0.70058(7) 1.03754(18) 0.0201(3) Uani 1 1 d . . . H4 H 0.0618 0.7063 0.9687 0.024 Uiso 1 1 calc R . . C20 C 0.30771(11) 0.54409(8) 1.1369(2) 0.0172(3) Uani 1 1 d . . . C24 C 0.34645(11) 0.61797(8) 0.9650(2) 0.0195(3) Uani 1 1 d . . . H24 H 0.3306 0.6494 0.8944 0.023 Uiso 1 1 calc R . . C28 C 0.16404(11) 0.53088(8) 1.1608(2) 0.0179(3) Uani 1 1 d . . . H28 H 0.1245 0.5096 1.2041 0.021 Uiso 1 1 calc R . . C29 C 0.03349(10) 0.58674(8) 1.02020(19) 0.0156(3) Uani 1 1 d . . . H29 H 0.0073 0.5546 1.0704 0.019 Uiso 1 1 calc R . . C30 C -0.00544(10) 0.58111(7) 0.84752(19) 0.0154(3) Uani 1 1 d . . . C21 C 0.39442(12) 0.52477(8) 1.1803(2) 0.0219(3) Uani 1 1 d . . . H21 H 0.4107 0.4942 1.2533 0.026 Uiso 1 1 calc R . . C23 C 0.43279(12) 0.59864(9) 1.0041(2) 0.0221(3) Uani 1 1 d . . . C34 C 0.00915(11) 0.64531(8) 1.08545(19) 0.0174(3) Uani 1 1 d . . . C31 C 0.02187(11) 0.55063(8) 0.7313(2) 0.0191(3) Uani 1 1 d . . . H31 H 0.0735 0.5287 0.7425 0.023 Uiso 1 1 calc R . . C22 C 0.45573(11) 0.55187(9) 1.1128(2) 0.0235(4) Uani 1 1 d . . . H22 H 0.5136 0.5388 1.1400 0.028 Uiso 1 1 calc R . . C37 C -0.00027(13) 0.74544(9) 1.1161(2) 0.0255(4) Uani 1 1 d . . . H37 H 0.0065 0.7867 1.1040 0.031 Uiso 1 1 calc R . . C35 C -0.03871(12) 0.65496(10) 1.1960(2) 0.0231(4) Uani 1 1 d . . . H35 H -0.0629 0.6255 1.2481 0.028 Uiso 1 1 calc R . . C36 C -0.04399(12) 0.71862(10) 1.2153(2) 0.0270(4) Uani 1 1 d . . . H36 H -0.0720 0.7383 1.2829 0.032 Uiso 1 1 calc R . . C32 C -0.04322(12) 0.55872(9) 0.5909(2) 0.0222(3) Uani 1 1 d . . . H32 H -0.0418 0.5432 0.4939 0.027 Uiso 1 1 calc R . . C022 C 0.50180(13) 0.62668(11) 0.9336(3) 0.0321(5) Uani 1 1 d . . . H02A H 0.5571 0.6074 0.9745 0.048 Uiso 1 1 calc R . . H02B H 0.5065 0.6689 0.9584 0.048 Uiso 1 1 calc R . . H02C H 0.4858 0.6217 0.8229 0.048 Uiso 1 1 calc R . . C33 C -0.10811(12) 0.59351(9) 0.6252(2) 0.0219(3) Uani 1 1 d . . . H33 H -0.1591 0.6058 0.5557 0.026 Uiso 1 1 calc R . . O2 O 0.50662(8) 0.59291(6) 0.52521(16) 0.0208(3) Uani 1 1 d . . . O1 O 0.42098(9) 0.73824(6) 0.24497(17) 0.0257(3) Uani 1 1 d . . . C6 C 0.38964(11) 0.65758(8) 0.4087(2) 0.0168(3) Uani 1 1 d . . . C8 C 0.54087(11) 0.67880(8) 0.3885(2) 0.0172(3) Uani 1 1 d . . . C10 C 0.64013(11) 0.67155(8) 0.43134(19) 0.0167(3) Uani 1 1 d . . . H10 H 0.6625 0.7065 0.3848 0.020 Uiso 1 1 calc R . . C7 C 0.48176(11) 0.63905(8) 0.44707(19) 0.0169(3) Uani 1 1 d . . . C11 C 0.68019(11) 0.67669(8) 0.60329(19) 0.0170(3) Uani 1 1 d . . . C16 C 0.64872(11) 0.55910(7) 0.3782(2) 0.0166(3) Uani 1 1 d . . . H16 H 0.6112 0.5471 0.4400 0.020 Uiso 1 1 calc R . . C5 C 0.32652(11) 0.62775(9) 0.4707(2) 0.0202(3) Uani 1 1 d . . . H5 H 0.3433 0.5948 0.5359 0.024 Uiso 1 1 calc R . . C15 C 0.67188(11) 0.61748(8) 0.35680(19) 0.0178(3) Uani 1 1 d . . . C1 C 0.36306(12) 0.70635(8) 0.3093(2) 0.0196(3) Uani 1 1 d . . . C3 C 0.21581(12) 0.69556(9) 0.3355(2) 0.0237(4) Uani 1 1 d . . . H3 H 0.1578 0.7084 0.3118 0.028 Uiso 1 1 calc R . . C4 C 0.23992(11) 0.64621(9) 0.4372(2) 0.0221(3) Uani 1 1 d . . . C14 C 0.76669(12) 0.69881(9) 0.8386(2) 0.0213(3) Uani 1 1 d . . . H14 H 0.8088 0.7171 0.9164 0.026 Uiso 1 1 calc R . . N1 N 0.74555(12) 0.71445(8) 0.6784(2) 0.0279(4) Uani 1 1 d . . . H1 H 0.7696 0.7427 0.6361 0.033 Uiso 1 1 calc R . . C2 C 0.27571(12) 0.72515(9) 0.2706(2) 0.0246(4) Uani 1 1 d . . . H2 H 0.2583 0.7571 0.2022 0.030 Uiso 1 1 calc R . . C13 C 0.71353(12) 0.65192(10) 0.8566(2) 0.0242(4) Uani 1 1 d . . . H13 H 0.7130 0.6323 0.9492 0.029 Uiso 1 1 calc R . . C9 C 0.50657(12) 0.72424(8) 0.2912(2) 0.0219(3) Uani 1 1 d . . . H9 H 0.5457 0.7479 0.2528 0.026 Uiso 1 1 calc R . . C12 C 0.66097(11) 0.63882(8) 0.71322(19) 0.0181(3) Uani 1 1 d . . . H12 H 0.6186 0.6087 0.6937 0.022 Uiso 1 1 calc R . . N2 N 0.72986(12) 0.61616(9) 0.2611(2) 0.0288(4) Uani 1 1 d . . . H2A H 0.7549 0.6469 0.2307 0.035 Uiso 1 1 calc R . . C18 C 0.74100(13) 0.55490(9) 0.2217(2) 0.0243(4) Uani 1 1 d . . . H18 H 0.7765 0.5406 0.1586 0.029 Uiso 1 1 calc R . . C17 C 0.68940(13) 0.52105(9) 0.2945(2) 0.0258(4) Uani 1 1 d . . . H17 H 0.6830 0.4794 0.2883 0.031 Uiso 1 1 calc R . . C19 C 0.17290(13) 0.61517(11) 0.5077(3) 0.0301(4) Uani 1 1 d . . . H19A H 0.1169 0.6341 0.4714 0.045 Uiso 1 1 calc R . . H19B H 0.1903 0.6181 0.6188 0.045 Uiso 1 1 calc R . . H19C H 0.1689 0.5735 0.4778 0.045 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 O4 0.0195(5) 0.0172(6) 0.0201(6) 0.0049(5) 0.0045(4) 0.0018(4) O3 0.0190(5) 0.0174(6) 0.0240(6) 0.0060(5) 0.0005(5) -0.0003(4) C26 0.0156(6) 0.0148(7) 0.0137(7) -0.0009(5) 0.0025(5) 0.0005(5) C25 0.0154(6) 0.0143(7) 0.0159(7) -0.0019(5) 0.0017(5) 0.0014(5) N3 0.0171(6) 0.0212(7) 0.0186(7) -0.0025(5) 0.0021(5) 0.0042(5) C27 0.0155(6) 0.0148(7) 0.0146(7) -0.0011(5) 0.0028(5) -0.0008(5) N4 0.0229(7) 0.0187(7) 0.0181(7) -0.0011(5) 0.0038(5) 0.0044(5) C20 0.0171(7) 0.0149(7) 0.0182(7) -0.0016(6) 0.0012(5) -0.0001(5) C24 0.0178(7) 0.0208(8) 0.0200(8) -0.0003(6) 0.0050(6) 0.0002(6) C28 0.0178(7) 0.0154(7) 0.0193(8) 0.0016(6) 0.0017(6) -0.0022(5) C29 0.0156(6) 0.0159(7) 0.0153(7) -0.0001(5) 0.0036(5) -0.0006(5) C30 0.0139(6) 0.0153(7) 0.0165(7) -0.0010(5) 0.0023(5) -0.0003(5) C21 0.0202(7) 0.0192(8) 0.0237(8) -0.0003(6) -0.0005(6) 0.0048(6) C23 0.0178(7) 0.0258(9) 0.0233(8) -0.0034(7) 0.0060(6) 0.0006(6) C34 0.0166(7) 0.0206(8) 0.0143(7) -0.0014(6) 0.0024(5) 0.0021(6) C31 0.0175(7) 0.0216(8) 0.0175(7) -0.0038(6) 0.0027(6) 0.0020(6) C22 0.0164(7) 0.0267(9) 0.0250(9) -0.0052(7) 0.0000(6) 0.0045(6) C37 0.0256(8) 0.0236(9) 0.0231(9) -0.0083(7) -0.0031(7) 0.0082(7) C35 0.0187(7) 0.0348(10) 0.0160(7) -0.0036(7) 0.0042(6) 0.0025(7) C36 0.0205(8) 0.0389(11) 0.0189(8) -0.0124(8) -0.0008(6) 0.0094(7) C32 0.0244(8) 0.0253(9) 0.0156(7) -0.0033(6) 0.0024(6) 0.0029(7) C022 0.0204(8) 0.0417(12) 0.0373(11) 0.0022(9) 0.0129(8) 0.0007(8) C33 0.0221(8) 0.0231(8) 0.0175(8) -0.0003(6) -0.0012(6) 0.0027(6) O2 0.0183(5) 0.0192(6) 0.0236(6) 0.0064(5) 0.0020(5) 0.0007(4) O1 0.0239(6) 0.0210(6) 0.0288(7) 0.0099(5) -0.0007(5) 0.0014(5) C6 0.0171(7) 0.0151(7) 0.0162(7) -0.0013(5) -0.0002(5) 0.0014(5) C8 0.0187(7) 0.0155(7) 0.0168(7) 0.0009(6) 0.0025(5) 0.0004(5) C10 0.0188(7) 0.0173(7) 0.0139(7) 0.0008(5) 0.0035(5) -0.0017(5) C7 0.0175(7) 0.0159(7) 0.0158(7) 0.0002(5) 0.0009(5) 0.0000(5) C11 0.0175(7) 0.0197(8) 0.0146(7) 0.0006(6) 0.0052(5) 0.0007(6) C16 0.0183(7) 0.0128(7) 0.0190(7) 0.0021(5) 0.0053(6) 0.0011(5) C5 0.0184(7) 0.0230(8) 0.0180(8) 0.0004(6) 0.0020(6) 0.0012(6) C15 0.0191(7) 0.0189(8) 0.0143(7) 0.0000(6) 0.0016(5) 0.0002(6) C1 0.0206(7) 0.0167(7) 0.0189(8) -0.0001(6) -0.0007(6) 0.0000(6) C3 0.0186(7) 0.0263(9) 0.0226(8) -0.0077(7) -0.0025(6) 0.0061(6) C4 0.0174(7) 0.0289(9) 0.0187(8) -0.0051(7) 0.0018(6) 0.0016(6) C14 0.0202(7) 0.0276(9) 0.0160(7) -0.0054(6) 0.0039(6) 0.0014(6) N1 0.0293(8) 0.0289(9) 0.0258(8) -0.0023(7) 0.0070(6) -0.0030(7) C2 0.0246(8) 0.0184(8) 0.0255(9) 0.0000(7) -0.0051(7) 0.0049(6) C13 0.0236(8) 0.0351(10) 0.0133(7) 0.0039(7) 0.0027(6) -0.0014(7) C9 0.0226(8) 0.0179(8) 0.0230(8) 0.0046(6) 0.0011(6) -0.0006(6) C12 0.0189(7) 0.0230(8) 0.0110(7) 0.0051(6) 0.0006(5) -0.0077(6) N2 0.0324(9) 0.0314(9) 0.0230(8) 0.0011(7) 0.0071(7) 0.0005(7) C18 0.0283(9) 0.0263(9) 0.0185(8) -0.0013(7) 0.0056(7) 0.0071(7) C17 0.0282(9) 0.0201(8) 0.0281(9) 0.0004(7) 0.0042(7) 0.0053(7) C19 0.0187(8) 0.0455(12) 0.0260(9) 0.0017(9) 0.0050(7) 0.0018(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 O4 C26 1.236(2) . ? O3 C28 1.351(2) . ? O3 C20 1.370(2) . ? C26 C27 1.463(2) . ? C26 C25 1.472(2) . ? C25 C20 1.393(2) . ? C25 C24 1.407(2) . ? N3 C30 1.368(2) . ? N3 C33 1.378(2) . ? N3 H3A 0.8600 . ? C27 C28 1.352(2) . ? C27 C29 1.517(2) . ? N4 C34 1.371(2) . ? N4 C37 1.375(2) . ? N4 H4 0.8600 . ? C20 C21 1.393(2) . ? C24 C23 1.386(2) . ? C24 H24 0.9300 . ? C28 H28 0.9300 . ? C29 C34 1.506(2) . ? C29 C30 1.514(2) . ? C29 H29 0.9800 . ? C30 C31 1.379(2) . ? C21 C22 1.382(3) . ? C21 H21 0.9300 . ? C23 C22 1.404(3) . ? C23 C022 1.504(3) . ? C34 C35 1.381(2) . ? C31 C32 1.425(2) . ? C31 H31 0.9300 . ? C22 H22 0.9300 . ? C37 C36 1.369(3) . ? C37 H37 0.9300 . ? C35 C36 1.427(3) . ? C35 H35 0.9300 . ? C36 H36 0.9300 . ? C32 C33 1.366(3) . ? C32 H32 0.9300 . ? C022 H02A 0.9600 . ? C022 H02B 0.9600 . ? C022 H02C 0.9600 . ? C33 H33 0.9300 . ? O2 C7 1.246(2) . ? O1 C9 1.346(2) . ? O1 C1 1.374(2) . ? C6 C1 1.396(2) . ? C6 C5 1.404(3) . ? C6 C7 1.465(2) . ? C8 C9 1.354(2) . ? C8 C7 1.459(2) . ? C8 C10 1.523(2) . ? C10 C15 1.508(2) . ? C10 C11 1.510(2) . ? C10 H10 0.9800 . ? C11 C12 1.370(2) . ? C11 N1 1.371(2) . ? C16 C15 1.370(2) . ? C16 C17 1.374(3) . ? C16 H16 0.9300 . ? C5 C4 1.384(2) . ? C5 H5 0.9300 . ? C15 N2 1.379(3) . ? C1 C2 1.397(3) . ? C3 C2 1.376(3) . ? C3 C4 1.411(3) . ? C3 H3 0.9300 . ? C4 C19 1.508(3) . ? C14 C13 1.365(3) . ? C14 N1 1.422(3) . ? C14 H14 0.9300 . ? N1 H1 0.8600 . ? C2 H2 0.9300 . ? C13 C12 1.374(2) . ? C13 H13 0.9300 . ? C9 H9 0.9300 . ? C12 H12 0.9300 . ? N2 C18 1.423(3) . ? N2 H2A 0.8600 . ? C18 C17 1.370(3) . ? C18 H18 0.9300 . ? C17 H17 0.9300 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? 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 C28 O3 C20 117.83(14) . . ? O4 C26 C27 123.96(15) . . ? O4 C26 C25 121.94(15) . . ? C27 C26 C25 114.09(14) . . ? C20 C25 C24 118.56(15) . . ? C20 C25 C26 120.32(15) . . ? C24 C25 C26 121.12(15) . . ? C30 N3 C33 110.19(15) . . ? C30 N3 H3A 124.9 . . ? C33 N3 H3A 124.9 . . ? C28 C27 C26 119.85(15) . . ? C28 C27 C29 118.65(15) . . ? C26 C27 C29 121.49(14) . . ? C34 N4 C37 109.76(16) . . ? C34 N4 H4 125.1 . . ? C37 N4 H4 125.1 . . ? O3 C20 C21 116.33(16) . . ? O3 C20 C25 122.20(15) . . ? C21 C20 C25 121.47(16) . . ? C23 C24 C25 120.94(17) . . ? C23 C24 H24 119.5 . . ? C25 C24 H24 119.5 . . ? O3 C28 C27 125.42(16) . . ? O3 C28 H28 117.3 . . ? C27 C28 H28 117.3 . . ? C34 C29 C30 112.29(14) . . ? C34 C29 C27 113.31(13) . . ? C30 C29 C27 111.19(13) . . ? C34 C29 H29 106.5 . . ? C30 C29 H29 106.5 . . ? C27 C29 H29 106.5 . . ? N3 C30 C31 107.05(15) . . ? N3 C30 C29 120.75(14) . . ? C31 C30 C29 132.13(15) . . ? C22 C21 C20 118.70(17) . . ? C22 C21 H21 120.6 . . ? C20 C21 H21 120.6 . . ? C24 C23 C22 118.71(17) . . ? C24 C23 C022 121.63(18) . . ? C22 C23 C022 119.66(17) . . ? N4 C34 C35 107.68(16) . . ? N4 C34 C29 123.03(15) . . ? C35 C34 C29 129.27(17) . . ? C30 C31 C32 107.74(15) . . ? C30 C31 H31 126.1 . . ? C32 C31 H31 126.1 . . ? C21 C22 C23 121.60(16) . . ? C21 C22 H22 119.2 . . ? C23 C22 H22 119.2 . . ? C36 C37 N4 107.87(18) . . ? C36 C37 H37 126.1 . . ? N4 C37 H37 126.1 . . ? C34 C35 C36 107.12(18) . . ? C34 C35 H35 126.4 . . ? C36 C35 H35 126.4 . . ? C37 C36 C35 107.56(17) . . ? C37 C36 H36 126.2 . . ? C35 C36 H36 126.2 . . ? C33 C32 C31 107.33(16) . . ? C33 C32 H32 126.3 . . ? C31 C32 H32 126.3 . . ? C23 C022 H02A 109.5 . . ? C23 C022 H02B 109.5 . . ? H02A C022 H02B 109.5 . . ? C23 C022 H02C 109.5 . . ? H02A C022 H02C 109.5 . . ? H02B C022 H02C 109.5 . . ? C32 C33 N3 107.68(15) . . ? C32 C33 H33 126.2 . . ? N3 C33 H33 126.2 . . ? C9 O1 C1 117.66(14) . . ? C1 C6 C5 118.49(16) . . ? C1 C6 C7 119.89(16) . . ? C5 C6 C7 121.63(15) . . ? C9 C8 C7 118.96(16) . . ? C9 C8 C10 118.00(16) . . ? C7 C8 C10 123.03(14) . . ? C15 C10 C11 113.47(14) . . ? C15 C10 C8 113.41(14) . . ? C11 C10 C8 113.93(14) . . ? C15 C10 H10 104.9 . . ? C11 C10 H10 104.9 . . ? C8 C10 H10 104.9 . . ? O2 C7 C8 123.39(15) . . ? O2 C7 C6 121.62(16) . . ? C8 C7 C6 114.98(15) . . ? C12 C11 N1 107.03(16) . . ? C12 C11 C10 124.09(16) . . ? N1 C11 C10 128.66(16) . . ? C15 C16 C17 109.54(16) . . ? C15 C16 H16 125.2 . . ? C17 C16 H16 125.2 . . ? C4 C5 C6 121.52(17) . . ? C4 C5 H5 119.2 . . ? C6 C5 H5 119.2 . . ? C16 C15 N2 107.38(16) . . ? C16 C15 C10 124.47(16) . . ? N2 C15 C10 128.12(16) . . ? O1 C1 C6 122.01(16) . . ? O1 C1 C2 116.75(16) . . ? C6 C1 C2 121.24(17) . . ? C2 C3 C4 121.86(17) . . ? C2 C3 H3 119.1 . . ? C4 C3 H3 119.1 . . ? C5 C4 C3 118.10(18) . . ? C5 C4 C19 121.34(18) . . ? C3 C4 C19 120.55(17) . . ? C13 C14 N1 107.11(16) . . ? C13 C14 H14 126.4 . . ? N1 C14 H14 126.4 . . ? C11 N1 C14 108.06(16) . . ? C11 N1 H1 126.0 . . ? C14 N1 H1 126.0 . . ? C3 C2 C1 118.76(17) . . ? C3 C2 H2 120.6 . . ? C1 C2 H2 120.6 . . ? C14 C13 C12 107.79(16) . . ? C14 C13 H13 126.1 . . ? C12 C13 H13 126.1 . . ? O1 C9 C8 125.90(17) . . ? O1 C9 H9 117.0 . . ? C8 C9 H9 117.0 . . ? C11 C12 C13 110.01(16) . . ? C11 C12 H12 125.0 . . ? C13 C12 H12 125.0 . . ? C15 N2 C18 107.88(17) . . ? C15 N2 H2A 126.1 . . ? C18 N2 H2A 126.1 . . ? C17 C18 N2 106.74(17) . . ? C17 C18 H18 126.6 . . ? N2 C18 H18 126.6 . . ? C18 C17 C16 108.44(18) . . ? C18 C17 H17 125.8 . . ? C16 C17 H17 125.8 . . ? C4 C19 H19A 109.5 . . ? C4 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C4 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? 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 O4 C26 C25 C20 174.94(16) . . . . ? C27 C26 C25 C20 -4.8(2) . . . . ? O4 C26 C25 C24 -4.8(3) . . . . ? C27 C26 C25 C24 175.48(15) . . . . ? O4 C26 C27 C28 -174.50(17) . . . . ? C25 C26 C27 C28 5.2(2) . . . . ? O4 C26 C27 C29 4.3(3) . . . . ? C25 C26 C27 C29 -175.94(14) . . . . ? C28 O3 C20 C21 -177.11(16) . . . . ? C28 O3 C20 C25 3.4(2) . . . . ? C24 C25 C20 O3 -179.67(15) . . . . ? C26 C25 C20 O3 0.6(2) . . . . ? C24 C25 C20 C21 0.9(3) . . . . ? C26 C25 C20 C21 -178.81(16) . . . . ? C20 C25 C24 C23 0.4(3) . . . . ? C26 C25 C24 C23 -179.87(16) . . . . ? C20 O3 C28 C27 -3.0(3) . . . . ? C26 C27 C28 O3 -1.5(3) . . . . ? C29 C27 C28 O3 179.63(16) . . . . ? C28 C27 C29 C34 109.43(18) . . . . ? C26 C27 C29 C34 -69.4(2) . . . . ? C28 C27 C29 C30 -122.98(17) . . . . ? C26 C27 C29 C30 58.2(2) . . . . ? C33 N3 C30 C31 0.3(2) . . . . ? C33 N3 C30 C29 -177.16(15) . . . . ? C34 C29 C30 N3 -31.6(2) . . . . ? C27 C29 C30 N3 -159.72(15) . . . . ? C34 C29 C30 C31 151.69(18) . . . . ? C27 C29 C30 C31 23.5(3) . . . . ? O3 C20 C21 C22 178.98(16) . . . . ? C25 C20 C21 C22 -1.6(3) . . . . ? C25 C24 C23 C22 -1.0(3) . . . . ? C25 C24 C23 C022 179.23(18) . . . . ? C37 N4 C34 C35 0.28(19) . . . . ? C37 N4 C34 C29 179.23(15) . . . . ? C30 C29 C34 N4 -61.3(2) . . . . ? C27 C29 C34 N4 65.7(2) . . . . ? C30 C29 C34 C35 117.38(19) . . . . ? C27 C29 C34 C35 -115.60(19) . . . . ? N3 C30 C31 C32 -0.1(2) . . . . ? C29 C30 C31 C32 176.99(18) . . . . ? C20 C21 C22 C23 0.9(3) . . . . ? C24 C23 C22 C21 0.3(3) . . . . ? C022 C23 C22 C21 -179.90(19) . . . . ? C34 N4 C37 C36 0.0(2) . . . . ? N4 C34 C35 C36 -0.5(2) . . . . ? C29 C34 C35 C36 -179.31(16) . . . . ? N4 C37 C36 C35 -0.3(2) . . . . ? C34 C35 C36 C37 0.5(2) . . . . ? C30 C31 C32 C33 -0.2(2) . . . . ? C31 C32 C33 N3 0.4(2) . . . . ? C30 N3 C33 C32 -0.4(2) . . . . ? C9 C8 C10 C15 -107.97(19) . . . . ? C7 C8 C10 C15 71.8(2) . . . . ? C9 C8 C10 C11 120.20(18) . . . . ? C7 C8 C10 C11 -60.0(2) . . . . ? C9 C8 C7 O2 173.14(18) . . . . ? C10 C8 C7 O2 -6.7(3) . . . . ? C9 C8 C7 C6 -7.5(2) . . . . ? C10 C8 C7 C6 172.74(15) . . . . ? C1 C6 C7 O2 -174.19(16) . . . . ? C5 C6 C7 O2 6.4(3) . . . . ? C1 C6 C7 C8 6.4(2) . . . . ? C5 C6 C7 C8 -172.98(16) . . . . ? C15 C10 C11 C12 -70.7(2) . . . . ? C8 C10 C11 C12 61.1(2) . . . . ? C15 C10 C11 N1 103.2(2) . . . . ? C8 C10 C11 N1 -125.01(19) . . . . ? C1 C6 C5 C4 -0.9(3) . . . . ? C7 C6 C5 C4 178.47(16) . . . . ? C17 C16 C15 N2 -1.5(2) . . . . ? C17 C16 C15 C10 -179.70(16) . . . . ? C11 C10 C15 C16 72.1(2) . . . . ? C8 C10 C15 C16 -59.9(2) . . . . ? C11 C10 C15 N2 -105.6(2) . . . . ? C8 C10 C15 N2 122.30(19) . . . . ? C9 O1 C1 C6 -5.5(3) . . . . ? C9 O1 C1 C2 174.38(17) . . . . ? C5 C6 C1 O1 179.38(16) . . . . ? C7 C6 C1 O1 0.0(3) . . . . ? C5 C6 C1 C2 -0.5(3) . . . . ? C7 C6 C1 C2 -179.94(16) . . . . ? C6 C5 C4 C3 1.2(3) . . . . ? C6 C5 C4 C19 -178.22(18) . . . . ? C2 C3 C4 C5 -0.1(3) . . . . ? C2 C3 C4 C19 179.37(18) . . . . ? C12 C11 N1 C14 0.2(2) . . . . ? C10 C11 N1 C14 -174.55(17) . . . . ? C13 C14 N1 C11 0.0(2) . . . . ? C4 C3 C2 C1 -1.3(3) . . . . ? O1 C1 C2 C3 -178.29(17) . . . . ? C6 C1 C2 C3 1.6(3) . . . . ? N1 C14 C13 C12 -0.1(2) . . . . ? C1 O1 C9 C8 4.5(3) . . . . ? C7 C8 C9 O1 2.3(3) . . . . ? C10 C8 C9 O1 -177.94(17) . . . . ? N1 C11 C12 C13 -0.3(2) . . . . ? C10 C11 C12 C13 174.76(17) . . . . ? C14 C13 C12 C11 0.3(2) . . . . ? C16 C15 N2 C18 0.9(2) . . . . ? C10 C15 N2 C18 178.98(16) . . . . ? C15 N2 C18 C17 0.1(2) . . . . ? N2 C18 C17 C16 -1.0(2) . . . . ? C15 C16 C17 C18 1.6(2) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.147 _refine_diff_density_min -0.176 _refine_diff_density_rms 0.138 data_7 _database_code_depnum_ccdc_archive 'CCDC 822934' #TrackingRef 'CIF-all.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H11 B F2 N2 O2' _chemical_melting_point ? _exptl_crystal_description plate _exptl_crystal_colour orange _diffrn_ambient_temperature 150(2) _chemical_formula_weight 336.10 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' B B 0.0013 0.0007 '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' _symmetry_int_tables_number 4 _chemical_absolute_configuration ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.5389(5) _cell_length_b 9.8159(5) _cell_length_c 9.8152(6) _cell_angle_alpha 90.00 _cell_angle_beta 95.303(5) _cell_angle_gamma 90.00 _cell_volume 723.23(7) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3612 _cell_measurement_theta_min 3.4100 _cell_measurement_theta_max 32.3244 _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.543 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 0.118 _exptl_absorpt_correction_T_min 0.9790 _exptl_absorpt_correction_T_max 0.9871 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_radiation_probe ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OXFORD DIFFRACTION XCALIBUR-S' _diffrn_measurement_method \w/q-scan _diffrn_detector_area_resol_mean 15.9948 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% <3%> _diffrn_reflns_number 3801 _diffrn_reflns_av_R_equivalents 0.0385 _diffrn_reflns_av_sigmaI/netI 0.0626 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.42 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2540 _reflns_number_gt 1930 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd.,' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Ortep3 _computing_publication_material Shelx97 _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^)+(0.0299P)^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 riding _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 -0.9(7) _refine_ls_number_reflns 2393 _refine_ls_number_parameters 226 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0427 _refine_ls_R_factor_gt 0.0320 _refine_ls_wR_factor_ref 0.0622 _refine_ls_wR_factor_gt 0.0603 _refine_ls_goodness_of_fit_ref 0.886 _refine_ls_restrained_S_all 0.886 _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 B1 B 0.2535(4) 0.1802(3) 0.7710(3) 0.0262(6) Uani 1 1 d . . . F1 F 0.41469(17) 0.23444(13) 0.73890(13) 0.0324(3) Uani 1 1 d . . . F2 F 0.22537(19) 0.05276(12) 0.71642(13) 0.0359(4) Uani 1 1 d . . . N1 N 0.1029(2) 0.27624(17) 0.71330(18) 0.0236(5) Uani 1 1 d . . . N2 N 0.2395(3) 0.62636(16) 1.0359(2) 0.0254(5) Uani 1 1 d . . . O1 O 0.2579(2) 0.16578(14) 0.92165(15) 0.0248(4) Uani 1 1 d . . . O2 O 0.2736(2) 0.46343(14) 1.21586(15) 0.0267(4) Uani 1 1 d . . . C1 C 0.2941(3) 0.2694(2) 1.0061(2) 0.0213(5) Uani 1 1 d . . . C2 C 0.3550(3) 0.2354(2) 1.1467(2) 0.0206(5) Uani 1 1 d . . . C3 C 0.4189(3) 0.1065(2) 1.1864(2) 0.0245(5) Uani 1 1 d . . . H3 H 0.4276 0.0379 1.1191 0.029 Uiso 1 1 calc R . . C4 C 0.4692(3) 0.0774(2) 1.3213(2) 0.0278(6) Uani 1 1 d . . . H4 H 0.5176 -0.0093 1.3464 0.033 Uiso 1 1 calc R . . C5 C 0.4491(3) 0.1751(2) 1.4203(2) 0.0310(6) Uani 1 1 d . . . H5 H 0.4815 0.1540 1.5138 0.037 Uiso 1 1 calc R . . C6 C 0.3824(3) 0.3032(2) 1.3855(2) 0.0301(6) Uani 1 1 d . . . H6 H 0.3660 0.3688 1.4545 0.036 Uiso 1 1 calc R . . C7 C 0.3402(3) 0.3342(2) 1.2493(2) 0.0240(5) Uani 1 1 d . . . C8 C 0.3285(3) 0.50444(19) 1.0864(2) 0.0232(5) Uani 1 1 d . . . H8 H 0.4606 0.5168 1.0924 0.028 Uiso 1 1 calc R . . C9 C 0.2689(3) 0.4038(2) 0.9747(2) 0.0205(5) Uani 1 1 d . . . C10 C -0.0125(3) 0.2508(2) 0.6034(2) 0.0322(6) Uani 1 1 d . . . H10 H -0.0272 0.1648 0.5593 0.039 Uiso 1 1 calc R . . C11 C -0.1077(4) 0.3684(2) 0.5632(3) 0.0338(6) Uani 1 1 d . . . H11 H -0.1968 0.3768 0.4886 0.041 Uiso 1 1 calc R . . C12 C -0.0474(3) 0.4695(2) 0.6524(2) 0.0291(6) Uani 1 1 d . . . H12 H -0.0871 0.5614 0.6504 0.035 Uiso 1 1 calc R . . C13 C 0.0830(3) 0.4132(2) 0.7470(2) 0.0227(5) Uani 1 1 d . . . C14 C 0.1688(3) 0.4712(2) 0.8650(2) 0.0224(5) Uani 1 1 d . . . C15 C 0.1586(3) 0.6117(2) 0.9038(2) 0.0238(5) Uani 1 1 d . . . C16 C 0.1092(3) 0.7400(2) 0.8569(2) 0.0285(6) Uani 1 1 d . . . H16 H 0.0514 0.7619 0.7695 0.034 Uiso 1 1 calc R . . C17 C 0.1606(3) 0.8319(2) 0.9629(3) 0.0291(6) Uani 1 1 d . . . H17 H 0.1420 0.9276 0.9599 0.035 Uiso 1 1 calc R . . C18 C 0.2426(3) 0.7602(2) 1.0721(3) 0.0290(6) Uani 1 1 d . . . H18 H 0.2918 0.7973 1.1566 0.035 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 B1 0.0362(18) 0.0230(14) 0.0188(15) -0.0028(12) -0.0002(13) 0.0004(12) F1 0.0329(9) 0.0397(7) 0.0243(8) -0.0013(6) 0.0015(6) 0.0037(6) F2 0.0556(10) 0.0250(7) 0.0250(8) -0.0064(6) -0.0071(7) 0.0057(6) N1 0.0267(12) 0.0264(10) 0.0173(11) 0.0008(8) -0.0007(9) 0.0009(8) N2 0.0286(12) 0.0203(10) 0.0269(12) -0.0036(8) 0.0010(10) 0.0022(8) O1 0.0349(10) 0.0213(8) 0.0174(9) -0.0029(7) -0.0018(7) 0.0023(7) O2 0.0366(10) 0.0224(8) 0.0213(9) -0.0027(7) 0.0043(7) 0.0025(7) C1 0.0179(13) 0.0256(13) 0.0206(13) -0.0037(10) 0.0043(9) -0.0007(9) C2 0.0191(12) 0.0240(11) 0.0184(12) 0.0000(10) 0.0007(9) -0.0023(9) C3 0.0239(14) 0.0267(13) 0.0229(13) -0.0021(10) 0.0026(11) 0.0010(10) C4 0.0276(14) 0.0318(13) 0.0238(14) 0.0063(11) 0.0003(11) 0.0030(10) C5 0.0386(16) 0.0360(14) 0.0174(14) 0.0027(12) -0.0036(12) 0.0004(11) C6 0.0386(16) 0.0336(15) 0.0173(14) -0.0079(10) -0.0014(12) -0.0048(11) C7 0.0264(14) 0.0230(12) 0.0225(14) -0.0012(10) 0.0015(11) -0.0036(10) C8 0.0269(13) 0.0209(12) 0.0220(14) 0.0024(10) 0.0032(10) 0.0005(9) C9 0.0202(13) 0.0197(12) 0.0220(13) 0.0003(9) 0.0037(10) 0.0000(9) C10 0.0410(16) 0.0329(13) 0.0218(14) -0.0007(11) -0.0030(12) -0.0020(11) C11 0.0347(16) 0.0407(15) 0.0236(15) 0.0020(11) -0.0098(12) 0.0033(11) C12 0.0302(15) 0.0296(13) 0.0269(14) 0.0047(11) -0.0005(11) 0.0038(11) C13 0.0245(14) 0.0225(12) 0.0214(13) 0.0027(10) 0.0040(11) -0.0008(10) C14 0.0213(13) 0.0228(12) 0.0239(13) 0.0029(10) 0.0061(10) -0.0030(10) C15 0.0205(14) 0.0250(12) 0.0262(14) 0.0001(11) 0.0032(11) 0.0010(10) C16 0.0272(15) 0.0271(12) 0.0310(15) 0.0044(11) 0.0022(11) 0.0018(10) C17 0.0279(15) 0.0193(12) 0.0411(17) 0.0001(12) 0.0084(12) 0.0014(10) C18 0.0333(14) 0.0184(12) 0.0362(15) -0.0037(11) 0.0072(12) -0.0007(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag B1 F2 1.369(3) . ? B1 F1 1.389(3) . ? B1 O1 1.483(3) . ? B1 N1 1.542(3) . ? N1 C10 1.345(3) . ? N1 C13 1.396(3) . ? N2 C18 1.361(3) . ? N2 C15 1.388(3) . ? N2 C8 1.437(3) . ? O1 C1 1.324(2) . ? O2 C7 1.393(3) . ? O2 C8 1.430(3) . ? C1 C9 1.365(3) . ? C1 C2 1.453(3) . ? C2 C3 1.396(3) . ? C2 C7 1.410(3) . ? C3 C4 1.372(3) . ? C3 H3 0.9500 . ? C4 C5 1.384(3) . ? C4 H4 0.9500 . ? C5 C6 1.385(3) . ? C5 H5 0.9500 . ? C6 C7 1.380(3) . ? C6 H6 0.9500 . ? C8 C9 1.512(3) . ? C8 H8 1.0000 . ? C9 C14 1.420(3) . ? C10 C11 1.397(3) . ? C10 H10 0.9500 . ? C11 C12 1.373(3) . ? C11 H11 0.9500 . ? C12 C13 1.402(3) . ? C12 H12 0.9500 . ? C13 C14 1.395(3) . ? C14 C15 1.434(3) . ? C15 C16 1.381(3) . ? C16 C17 1.404(3) . ? C16 H16 0.9500 . ? C17 C18 1.379(3) . ? C17 H17 0.9500 . ? C18 H18 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 F2 B1 F1 111.6(2) . . ? F2 B1 O1 106.92(19) . . ? F1 B1 O1 108.9(2) . . ? F2 B1 N1 109.4(2) . . ? F1 B1 N1 108.19(18) . . ? O1 B1 N1 111.85(19) . . ? C10 N1 C13 107.04(19) . . ? C10 N1 B1 125.48(19) . . ? C13 N1 B1 126.39(18) . . ? C18 N2 C15 109.85(18) . . ? C18 N2 C8 135.9(2) . . ? C15 N2 C8 112.73(16) . . ? C1 O1 B1 122.35(17) . . ? C7 O2 C8 109.76(15) . . ? O1 C1 C9 125.8(2) . . ? O1 C1 C2 116.55(19) . . ? C9 C1 C2 117.49(19) . . ? C3 C2 C7 118.2(2) . . ? C3 C2 C1 122.9(2) . . ? C7 C2 C1 118.79(19) . . ? C4 C3 C2 121.0(2) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C3 C4 C5 119.7(2) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? C4 C5 C6 121.1(2) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C7 C6 C5 119.0(2) . . ? C7 C6 H6 120.5 . . ? C5 C6 H6 120.5 . . ? C6 C7 O2 118.35(19) . . ? C6 C7 C2 121.0(2) . . ? O2 C7 C2 120.6(2) . . ? O2 C8 N2 112.14(18) . . ? O2 C8 C9 111.68(16) . . ? N2 C8 C9 101.30(18) . . ? O2 C8 H8 110.5 . . ? N2 C8 H8 110.5 . . ? C9 C8 H8 110.5 . . ? C1 C9 C14 132.4(2) . . ? C1 C9 C8 116.26(19) . . ? C14 C9 C8 110.29(17) . . ? N1 C10 C11 110.5(2) . . ? N1 C10 H10 124.7 . . ? C11 C10 H10 124.7 . . ? C12 C11 C10 106.6(2) . . ? C12 C11 H11 126.7 . . ? C10 C11 H11 126.7 . . ? C11 C12 C13 108.0(2) . . ? C11 C12 H12 126.0 . . ? C13 C12 H12 126.0 . . ? C14 C13 N1 122.6(2) . . ? C14 C13 C12 129.21(19) . . ? N1 C13 C12 107.9(2) . . ? C13 C14 C9 127.78(19) . . ? C13 C14 C15 125.5(2) . . ? C9 C14 C15 106.5(2) . . ? C16 C15 N2 107.39(19) . . ? C16 C15 C14 143.8(2) . . ? N2 C15 C14 108.57(18) . . ? C15 C16 C17 106.9(2) . . ? C15 C16 H16 126.5 . . ? C17 C16 H16 126.5 . . ? C18 C17 C16 108.8(2) . . ? C18 C17 H17 125.6 . . ? C16 C17 H17 125.6 . . ? N2 C18 C17 107.1(2) . . ? N2 C18 H18 126.5 . . ? C17 C18 H18 126.5 . . ? 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 F2 B1 N1 C10 -15.1(3) . . . . ? F1 B1 N1 C10 106.7(2) . . . . ? O1 B1 N1 C10 -133.4(2) . . . . ? F2 B1 N1 C13 178.39(19) . . . . ? F1 B1 N1 C13 -59.8(3) . . . . ? O1 B1 N1 C13 60.1(3) . . . . ? F2 B1 O1 C1 175.63(18) . . . . ? F1 B1 O1 C1 54.9(3) . . . . ? N1 B1 O1 C1 -64.6(3) . . . . ? B1 O1 C1 C9 25.1(3) . . . . ? B1 O1 C1 C2 -159.2(2) . . . . ? O1 C1 C2 C3 16.9(3) . . . . ? C9 C1 C2 C3 -167.1(2) . . . . ? O1 C1 C2 C7 -159.5(2) . . . . ? C9 C1 C2 C7 16.5(3) . . . . ? C7 C2 C3 C4 -1.3(3) . . . . ? C1 C2 C3 C4 -177.7(2) . . . . ? C2 C3 C4 C5 2.9(3) . . . . ? C3 C4 C5 C6 -1.4(4) . . . . ? C4 C5 C6 C7 -1.7(4) . . . . ? C5 C6 C7 O2 -179.9(2) . . . . ? C5 C6 C7 C2 3.4(3) . . . . ? C8 O2 C7 C6 148.1(2) . . . . ? C8 O2 C7 C2 -35.2(3) . . . . ? C3 C2 C7 C6 -1.9(3) . . . . ? C1 C2 C7 C6 174.6(2) . . . . ? C3 C2 C7 O2 -178.55(19) . . . . ? C1 C2 C7 O2 -2.0(3) . . . . ? C7 O2 C8 N2 170.19(18) . . . . ? C7 O2 C8 C9 57.3(2) . . . . ? C18 N2 C8 O2 69.0(3) . . . . ? C15 N2 C8 O2 -127.21(19) . . . . ? C18 N2 C8 C9 -171.8(2) . . . . ? C15 N2 C8 C9 -8.0(2) . . . . ? O1 C1 C9 C14 15.7(4) . . . . ? C2 C1 C9 C14 -160.0(2) . . . . ? O1 C1 C9 C8 -177.23(19) . . . . ? C2 C1 C9 C8 7.1(3) . . . . ? O2 C8 C9 C1 -44.9(3) . . . . ? N2 C8 C9 C1 -164.43(19) . . . . ? O2 C8 C9 C14 125.00(19) . . . . ? N2 C8 C9 C14 5.5(2) . . . . ? C13 N1 C10 C11 0.4(3) . . . . ? B1 N1 C10 C11 -168.3(2) . . . . ? N1 C10 C11 C12 0.0(3) . . . . ? C10 C11 C12 C13 -0.4(3) . . . . ? C10 N1 C13 C14 173.1(2) . . . . ? B1 N1 C13 C14 -18.4(3) . . . . ? C10 N1 C13 C12 -0.6(2) . . . . ? B1 N1 C13 C12 167.9(2) . . . . ? C11 C12 C13 C14 -172.5(2) . . . . ? C11 C12 C13 N1 0.6(3) . . . . ? N1 C13 C14 C9 -7.9(3) . . . . ? C12 C13 C14 C9 164.3(2) . . . . ? N1 C13 C14 C15 178.05(19) . . . . ? C12 C13 C14 C15 -9.7(4) . . . . ? C1 C9 C14 C13 -8.5(4) . . . . ? C8 C9 C14 C13 -176.2(2) . . . . ? C1 C9 C14 C15 166.4(2) . . . . ? C8 C9 C14 C15 -1.3(2) . . . . ? C18 N2 C15 C16 -0.3(2) . . . . ? C8 N2 C15 C16 -168.4(2) . . . . ? C18 N2 C15 C14 175.89(18) . . . . ? C8 N2 C15 C14 7.8(2) . . . . ? C13 C14 C15 C16 -14.9(5) . . . . ? C9 C14 C15 C16 170.1(3) . . . . ? C13 C14 C15 N2 171.3(2) . . . . ? C9 C14 C15 N2 -3.8(2) . . . . ? N2 C15 C16 C17 -0.3(2) . . . . ? C14 C15 C16 C17 -174.2(3) . . . . ? C15 C16 C17 C18 0.8(3) . . . . ? C15 N2 C18 C17 0.8(2) . . . . ? C8 N2 C18 C17 165.0(2) . . . . ? C16 C17 C18 N2 -1.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.135 _refine_diff_density_min -0.182 _refine_diff_density_rms 0.037 data_8 _database_code_depnum_ccdc_archive 'CCDC 822935' #TrackingRef 'CIF-all.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H13 B F2 N2 O2' _chemical_melting_point ? _exptl_crystal_description block _exptl_crystal_colour orange _diffrn_ambient_temperature 150(2) _chemical_formula_weight 350.12 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' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C c' _symmetry_int_tables_number 9 _chemical_absolute_configuration ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 12.4354(7) _cell_length_b 16.4185(9) _cell_length_c 7.8451(5) _cell_angle_alpha 90.00 _cell_angle_beta 99.368(5) _cell_angle_gamma 90.00 _cell_volume 1580.38(16) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3663 _cell_measurement_theta_min 3.3138 _cell_measurement_theta_max 32.7399 _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.472 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 0.111 _exptl_absorpt_correction_T_min 0.9641 _exptl_absorpt_correction_T_max 0.9748 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_radiation_probe ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OXFORD DIFFRACTION XCALIBUR-S' _diffrn_measurement_method \w/q-scan _diffrn_detector_area_resol_mean 15.9948 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% <3%> _diffrn_reflns_number 5036 _diffrn_reflns_av_R_equivalents 0.0298 _diffrn_reflns_av_sigmaI/netI 0.0308 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.32 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2789 _reflns_number_gt 1929 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd.,' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Ortep3 _computing_publication_material Shelx97 _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^)+(0.0413P)^2^+0.0653P] 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 riding _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 0.7(7) _refine_ls_number_reflns 2096 _refine_ls_number_parameters 236 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0346 _refine_ls_R_factor_gt 0.0307 _refine_ls_wR_factor_ref 0.0688 _refine_ls_wR_factor_gt 0.0677 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _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 B1 B 0.7235(2) 0.25884(16) 0.6310(4) 0.0258(6) Uani 1 1 d . . . F1 F 0.78163(11) 0.24356(8) 0.79310(19) 0.0334(3) Uani 1 1 d . . . F2 F 0.63009(10) 0.21221(8) 0.5979(2) 0.0358(4) Uani 1 1 d . . . N1 N 0.79469(14) 0.23859(11) 0.4911(3) 0.0221(4) Uani 1 1 d . . . N2 N 1.02315(14) 0.46891(11) 0.6034(2) 0.0216(4) Uani 1 1 d . . . O1 O 0.68755(11) 0.34532(9) 0.6216(2) 0.0242(4) Uani 1 1 d . . . O2 O 0.86790(11) 0.55218(9) 0.5957(2) 0.0245(4) Uani 1 1 d . . . C1 C 0.75480(17) 0.40703(14) 0.6461(3) 0.0207(5) Uani 1 1 d . . . C2 C 0.70953(17) 0.48643(14) 0.6774(3) 0.0216(5) Uani 1 1 d . . . C3 C 0.60650(17) 0.49496(16) 0.7261(3) 0.0261(5) Uani 1 1 d . . . H3 H 0.5679 0.4477 0.7515 0.031 Uiso 1 1 calc R . . C4 C 0.55981(17) 0.57101(15) 0.7381(3) 0.0293(6) Uani 1 1 d . . . C5 C 0.4514(2) 0.58014(19) 0.8001(4) 0.0424(7) Uani 1 1 d . . . H5A H 0.3950 0.5946 0.7024 0.064 Uiso 1 1 calc R . . H5B H 0.4568 0.6232 0.8877 0.064 Uiso 1 1 calc R . . H5C H 0.4321 0.5286 0.8505 0.064 Uiso 1 1 calc R . . C6 C 0.61689(18) 0.63896(15) 0.6945(3) 0.0312(6) Uani 1 1 d . . . H6 H 0.5846 0.6912 0.6981 0.037 Uiso 1 1 calc R . . C7 C 0.71879(18) 0.63312(15) 0.6461(3) 0.0275(5) Uani 1 1 d . . . H7 H 0.7556 0.6805 0.6165 0.033 Uiso 1 1 calc R . . C8 C 0.76590(17) 0.55710(14) 0.6418(3) 0.0236(5) Uani 1 1 d . . . C9 C 0.92599(17) 0.48354(14) 0.6757(3) 0.0214(5) Uani 1 1 d . . . H9 H 0.9436 0.4910 0.8037 0.026 Uiso 1 1 calc R . . C10 C 0.86368(17) 0.40523(14) 0.6309(3) 0.0205(5) Uani 1 1 d . . . C11 C 0.78106(18) 0.17460(14) 0.3835(3) 0.0267(5) Uani 1 1 d . . . H11 H 0.7207 0.1384 0.3714 0.032 Uiso 1 1 calc R . . C12 C 0.86775(18) 0.16855(15) 0.2919(3) 0.0295(5) Uani 1 1 d . . . H12 H 0.8766 0.1288 0.2072 0.035 Uiso 1 1 calc R . . C13 C 0.93804(17) 0.23126(14) 0.3477(3) 0.0248(5) Uani 1 1 d . . . H13 H 1.0052 0.2423 0.3095 0.030 Uiso 1 1 calc R . . C14 C 0.89288(16) 0.27599(14) 0.4711(3) 0.0211(5) Uani 1 1 d . . . C15 C 0.92555(16) 0.35056(13) 0.5473(3) 0.0195(5) Uani 1 1 d . . . C16 C 1.02758(17) 0.39127(13) 0.5364(3) 0.0217(5) Uani 1 1 d . . . C17 C 1.12690(16) 0.38289(15) 0.4825(3) 0.0237(5) Uani 1 1 d . . . H17 H 1.1535 0.3359 0.4324 0.028 Uiso 1 1 calc R . . C18 C 1.18121(17) 0.45780(15) 0.5166(3) 0.0267(5) Uani 1 1 d . . . H18 H 1.2514 0.4703 0.4908 0.032 Uiso 1 1 calc R . . C19 C 1.11701(17) 0.50984(15) 0.5926(3) 0.0255(5) Uani 1 1 d . . . H19 H 1.1346 0.5639 0.6305 0.031 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 B1 0.0300(13) 0.0190(14) 0.0303(17) 0.0005(12) 0.0106(12) -0.0002(10) F1 0.0460(8) 0.0302(8) 0.0270(8) 0.0054(7) 0.0148(6) 0.0056(6) F2 0.0353(7) 0.0240(7) 0.0529(10) -0.0035(7) 0.0216(6) -0.0066(6) N1 0.0256(9) 0.0156(10) 0.0257(11) 0.0007(9) 0.0062(8) -0.0003(7) N2 0.0238(9) 0.0222(11) 0.0190(11) -0.0011(8) 0.0039(8) -0.0017(8) O1 0.0245(8) 0.0195(8) 0.0306(10) -0.0008(7) 0.0105(7) -0.0011(6) O2 0.0272(8) 0.0190(9) 0.0278(10) 0.0018(7) 0.0061(7) 0.0010(6) C1 0.0266(11) 0.0204(12) 0.0159(11) 0.0023(10) 0.0059(9) 0.0018(9) C2 0.0265(11) 0.0208(12) 0.0169(12) -0.0031(10) 0.0015(9) 0.0031(9) C3 0.0259(12) 0.0286(13) 0.0235(14) 0.0006(11) 0.0029(10) 0.0016(9) C4 0.0268(12) 0.0328(15) 0.0265(14) -0.0048(12) -0.0010(10) 0.0064(10) C5 0.0354(14) 0.0429(17) 0.0501(19) -0.0072(14) 0.0104(13) 0.0135(11) C6 0.0349(13) 0.0242(13) 0.0320(15) -0.0075(12) -0.0025(10) 0.0122(10) C7 0.0332(13) 0.0209(12) 0.0270(14) -0.0024(11) 0.0006(10) 0.0013(9) C8 0.0270(12) 0.0244(12) 0.0187(12) -0.0032(11) 0.0011(10) 0.0022(9) C9 0.0249(11) 0.0211(12) 0.0185(13) -0.0009(10) 0.0048(9) 0.0005(9) C10 0.0259(11) 0.0201(12) 0.0155(12) 0.0004(10) 0.0032(9) -0.0005(9) C11 0.0296(12) 0.0182(12) 0.0332(14) 0.0003(11) 0.0076(10) -0.0019(10) C12 0.0337(13) 0.0256(13) 0.0299(14) -0.0089(11) 0.0077(10) 0.0024(10) C13 0.0232(11) 0.0253(13) 0.0274(14) -0.0008(11) 0.0084(9) 0.0017(9) C14 0.0203(11) 0.0207(12) 0.0226(13) 0.0019(10) 0.0044(9) 0.0023(8) C15 0.0215(11) 0.0215(12) 0.0156(11) 0.0038(10) 0.0031(9) 0.0033(9) C16 0.0269(11) 0.0212(13) 0.0161(12) -0.0004(10) 0.0009(9) 0.0022(9) C17 0.0225(11) 0.0282(13) 0.0207(13) -0.0001(11) 0.0047(9) 0.0018(9) C18 0.0248(12) 0.0340(15) 0.0217(14) 0.0008(11) 0.0050(9) -0.0029(10) C19 0.0261(12) 0.0273(13) 0.0223(13) -0.0004(11) 0.0010(9) -0.0060(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag B1 F1 1.379(3) . ? B1 F2 1.380(3) . ? B1 O1 1.487(3) . ? B1 N1 1.554(3) . ? N1 C11 1.341(3) . ? N1 C14 1.398(3) . ? N2 C19 1.361(3) . ? N2 C16 1.383(3) . ? N2 C9 1.436(3) . ? O1 C1 1.308(3) . ? O2 C8 1.377(3) . ? O2 C9 1.428(3) . ? C1 C10 1.379(3) . ? C1 C2 1.457(3) . ? C2 C3 1.403(3) . ? C2 C8 1.407(3) . ? C3 C4 1.387(3) . ? C3 H3 0.9500 . ? C4 C6 1.395(4) . ? C4 C5 1.514(3) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 C7 1.384(3) . ? C6 H6 0.9500 . ? C7 C8 1.382(3) . ? C7 H7 0.9500 . ? C9 C10 1.513(3) . ? C9 H9 1.0000 . ? C10 C15 1.412(3) . ? C11 C12 1.393(3) . ? C11 H11 0.9500 . ? C12 C13 1.375(3) . ? C12 H12 0.9500 . ? C13 C14 1.403(3) . ? C13 H13 0.9500 . ? C14 C15 1.393(3) . ? C15 C16 1.449(3) . ? C16 C17 1.376(3) . ? C17 C18 1.408(3) . ? C17 H17 0.9500 . ? C18 C19 1.371(3) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag F1 B1 F2 111.8(2) . . ? F1 B1 O1 109.1(2) . . ? F2 B1 O1 106.47(18) . . ? F1 B1 N1 109.79(18) . . ? F2 B1 N1 107.9(2) . . ? O1 B1 N1 111.74(19) . . ? C11 N1 C14 107.26(18) . . ? C11 N1 B1 125.73(19) . . ? C14 N1 B1 126.41(19) . . ? C19 N2 C16 110.11(18) . . ? C19 N2 C9 136.6(2) . . ? C16 N2 C9 113.09(17) . . ? C1 O1 B1 123.55(17) . . ? C8 O2 C9 110.67(16) . . ? O1 C1 C10 125.8(2) . . ? O1 C1 C2 117.56(18) . . ? C10 C1 C2 116.5(2) . . ? C3 C2 C8 118.59(19) . . ? C3 C2 C1 122.1(2) . . ? C8 C2 C1 119.07(19) . . ? C4 C3 C2 121.3(2) . . ? C4 C3 H3 119.3 . . ? C2 C3 H3 119.3 . . ? C3 C4 C6 117.9(2) . . ? C3 C4 C5 121.0(2) . . ? C6 C4 C5 121.0(2) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C7 C6 C4 122.5(2) . . ? C7 C6 H6 118.8 . . ? C4 C6 H6 118.8 . . ? C8 C7 C6 118.7(2) . . ? C8 C7 H7 120.7 . . ? C6 C7 H7 120.7 . . ? O2 C8 C7 118.2(2) . . ? O2 C8 C2 120.92(19) . . ? C7 C8 C2 120.88(19) . . ? O2 C9 N2 110.88(17) . . ? O2 C9 C10 111.43(18) . . ? N2 C9 C10 101.43(18) . . ? O2 C9 H9 110.9 . . ? N2 C9 H9 110.9 . . ? C10 C9 H9 110.9 . . ? C1 C10 C15 132.1(2) . . ? C1 C10 C9 115.8(2) . . ? C15 C10 C9 110.55(19) . . ? N1 C11 C12 110.58(19) . . ? N1 C11 H11 124.7 . . ? C12 C11 H11 124.7 . . ? C13 C12 C11 106.7(2) . . ? C13 C12 H12 126.6 . . ? C11 C12 H12 126.6 . . ? C12 C13 C14 107.86(19) . . ? C12 C13 H13 126.1 . . ? C14 C13 H13 126.1 . . ? C15 C14 N1 122.47(19) . . ? C15 C14 C13 129.35(19) . . ? N1 C14 C13 107.60(19) . . ? C14 C15 C10 127.95(19) . . ? C14 C15 C16 125.25(19) . . ? C10 C15 C16 106.4(2) . . ? C17 C16 N2 107.58(18) . . ? C17 C16 C15 144.1(2) . . ? N2 C16 C15 108.27(18) . . ? C16 C17 C18 106.3(2) . . ? C16 C17 H17 126.8 . . ? C18 C17 H17 126.8 . . ? C19 C18 C17 109.37(19) . . ? C19 C18 H18 125.3 . . ? C17 C18 H18 125.3 . . ? N2 C19 C18 106.6(2) . . ? N2 C19 H19 126.7 . . ? C18 C19 H19 126.7 . . ? 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 F1 B1 N1 C11 107.8(3) . . . . ? F2 B1 N1 C11 -14.3(3) . . . . ? O1 B1 N1 C11 -131.0(2) . . . . ? F1 B1 N1 C14 -62.1(3) . . . . ? F2 B1 N1 C14 175.81(19) . . . . ? O1 B1 N1 C14 59.1(3) . . . . ? F1 B1 O1 C1 59.3(3) . . . . ? F2 B1 O1 C1 -179.9(2) . . . . ? N1 B1 O1 C1 -62.3(3) . . . . ? B1 O1 C1 C10 21.2(3) . . . . ? B1 O1 C1 C2 -164.5(2) . . . . ? O1 C1 C2 C3 16.9(3) . . . . ? C10 C1 C2 C3 -168.2(2) . . . . ? O1 C1 C2 C8 -156.8(2) . . . . ? C10 C1 C2 C8 18.0(3) . . . . ? C8 C2 C3 C4 0.5(3) . . . . ? C1 C2 C3 C4 -173.3(2) . . . . ? C2 C3 C4 C6 2.1(3) . . . . ? C2 C3 C4 C5 -176.6(2) . . . . ? C3 C4 C6 C7 -2.3(4) . . . . ? C5 C4 C6 C7 176.5(2) . . . . ? C4 C6 C7 C8 -0.3(4) . . . . ? C9 O2 C8 C7 151.1(2) . . . . ? C9 O2 C8 C2 -31.2(3) . . . . ? C6 C7 C8 O2 -179.1(2) . . . . ? C6 C7 C8 C2 3.1(3) . . . . ? C3 C2 C8 O2 179.1(2) . . . . ? C1 C2 C8 O2 -6.9(3) . . . . ? C3 C2 C8 C7 -3.2(3) . . . . ? C1 C2 C8 C7 170.8(2) . . . . ? C8 O2 C9 N2 168.96(18) . . . . ? C8 O2 C9 C10 56.8(2) . . . . ? C19 N2 C9 O2 62.3(3) . . . . ? C16 N2 C9 O2 -123.09(19) . . . . ? C19 N2 C9 C10 -179.3(2) . . . . ? C16 N2 C9 C10 -4.7(2) . . . . ? O1 C1 C10 C15 19.0(4) . . . . ? C2 C1 C10 C15 -155.4(2) . . . . ? O1 C1 C10 C9 -176.6(2) . . . . ? C2 C1 C10 C9 9.0(3) . . . . ? O2 C9 C10 C1 -47.0(3) . . . . ? N2 C9 C10 C1 -165.02(19) . . . . ? O2 C9 C10 C15 120.7(2) . . . . ? N2 C9 C10 C15 2.6(3) . . . . ? C14 N1 C11 C12 -0.1(3) . . . . ? B1 N1 C11 C12 -171.7(2) . . . . ? N1 C11 C12 C13 0.7(3) . . . . ? C11 C12 C13 C14 -0.9(3) . . . . ? C11 N1 C14 C15 171.6(2) . . . . ? B1 N1 C14 C15 -17.0(3) . . . . ? C11 N1 C14 C13 -0.4(2) . . . . ? B1 N1 C14 C13 171.0(2) . . . . ? C12 C13 C14 C15 -170.4(2) . . . . ? C12 C13 C14 N1 0.9(3) . . . . ? N1 C14 C15 C10 -10.1(4) . . . . ? C13 C14 C15 C10 160.1(2) . . . . ? N1 C14 C15 C16 177.9(2) . . . . ? C13 C14 C15 C16 -12.0(4) . . . . ? C1 C10 C15 C14 -8.2(4) . . . . ? C9 C10 C15 C14 -173.1(2) . . . . ? C1 C10 C15 C16 165.1(2) . . . . ? C9 C10 C15 C16 0.1(3) . . . . ? C19 N2 C16 C17 0.2(2) . . . . ? C9 N2 C16 C17 -175.9(2) . . . . ? C19 N2 C16 C15 -178.9(2) . . . . ? C9 N2 C16 C15 5.0(2) . . . . ? C14 C15 C16 C17 -8.1(5) . . . . ? C10 C15 C16 C17 178.4(3) . . . . ? C14 C15 C16 N2 170.4(2) . . . . ? C10 C15 C16 N2 -3.0(2) . . . . ? N2 C16 C17 C18 -0.8(2) . . . . ? C15 C16 C17 C18 177.7(3) . . . . ? C16 C17 C18 C19 1.2(3) . . . . ? C16 N2 C19 C18 0.5(3) . . . . ? C9 N2 C19 C18 175.3(2) . . . . ? C17 C18 C19 N2 -1.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.142 _refine_diff_density_min -0.193 _refine_diff_density_rms 0.043 data_9 _database_code_depnum_ccdc_archive 'CCDC 873216' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C21 H15 B F2 N2 O2' _chemical_formula_sum 'C21 H15 B F2 N2 O2' _chemical_melting_point ? _exptl_crystal_description Block _exptl_crystal_colour Orange _diffrn_ambient_temperature 296(2) _chemical_formula_weight 376.16 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' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_int_tables_number 14 _chemical_absolute_configuration ? 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 6.2233(15) _cell_length_b 21.974(5) _cell_length_c 13.118(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.286(4) _cell_angle_gamma 90.00 _cell_volume 1793.4(8) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2575 _cell_measurement_theta_min 0.977 _cell_measurement_theta_max 0.983 _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.393 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_radiation_probe ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 13574 _diffrn_reflns_av_R_equivalents 0.0360 _diffrn_reflns_av_sigmaI/netI 0.0320 _diffrn_reflns_limit_h_min -3 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 23.28 _reflns_number_total 2575 _reflns_number_gt 1777 _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^)+(0.1400P)^2^+0.3422P] 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 none _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2567 _refine_ls_number_parameters 254 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0828 _refine_ls_R_factor_gt 0.0556 _refine_ls_wR_factor_ref 0.1960 _refine_ls_wR_factor_gt 0.1600 _refine_ls_goodness_of_fit_ref 0.964 _refine_ls_restrained_S_all 0.964 _refine_ls_shift/su_max 0.028 _refine_ls_shift/su_mean 0.013 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 F1 F 0.4543(4) 0.75667(13) 0.47347(18) 0.0926(9) Uani 1 1 d . . . F2 F 0.8001(4) 0.78119(10) 0.51707(18) 0.0843(8) Uani 1 1 d . . . O1 O 0.6813(4) 0.68210(12) 0.52810(17) 0.0609(7) Uani 1 1 d . . . O2 O 1.1445(4) 0.55040(11) 0.54364(18) 0.0605(7) Uani 1 1 d . . . N1 N 0.7255(4) 0.73236(14) 0.3569(2) 0.0565(8) Uani 1 1 d . . . N2 N 1.3152(4) 0.59936(13) 0.4075(2) 0.0546(8) Uani 1 1 d . . . C1 C 0.7369(10) 0.5917(4) 0.9776(4) 0.134(2) Uani 1 1 d . . . H1A H 0.8496 0.6206 0.9665 0.201 Uiso 1 1 calc R . . H1B H 0.7986 0.5531 0.9959 0.201 Uiso 1 1 calc R . . H1C H 0.6482 0.6057 1.0318 0.201 Uiso 1 1 calc R . . C2 C 0.6058(8) 0.5851(4) 0.8841(4) 0.152(3) Uani 1 1 d . . . H2 H 0.5959 0.5411 0.8957 0.182 Uiso 1 1 calc R . . C4 C 0.7377(7) 0.5737(3) 0.7899(3) 0.0817(14) Uani 1 1 d . . . C5 C 0.7350(6) 0.6151(2) 0.7104(3) 0.0685(11) Uani 1 1 d . . . H4 H 0.6421 0.6482 0.7129 0.082 Uiso 1 1 calc R . . C6 C 0.8664(5) 0.60881(18) 0.6269(3) 0.0560(10) Uani 1 1 d . . . C10 C 0.8581(5) 0.64955(16) 0.5393(2) 0.0505(9) Uani 1 1 d . . . C11 C 1.0236(5) 0.64735(15) 0.4735(2) 0.0470(8) Uani 1 1 d . . . C13 C 1.0422(5) 0.66649(15) 0.3710(2) 0.0480(9) Uani 1 1 d . . . C14 C 1.2260(5) 0.63592(16) 0.3312(3) 0.0514(9) Uani 1 1 d . . . C15 C 1.3527(6) 0.62968(17) 0.2471(3) 0.0623(10) Uani 1 1 d . . . H10 H 1.3319 0.6486 0.1842 0.075 Uiso 1 1 calc R . . C16 C 1.5185(6) 0.58947(18) 0.2743(3) 0.0679(11) Uani 1 1 d . . . H11 H 1.6277 0.5767 0.2320 0.082 Uiso 1 1 calc R . . C20 C 0.7213(7) 0.75003(19) 0.1882(3) 0.0719(12) Uani 1 1 d . . . H12 H 0.6773 0.7644 0.1244 0.086 Uiso 1 1 calc R . . C19 C 0.8976(6) 0.71503(16) 0.2096(3) 0.0592(10) Uani 1 1 d . . . H13 H 0.9966 0.7013 0.1628 0.071 Uiso 1 1 calc R . . C18 C 0.9030(5) 0.70353(15) 0.3143(3) 0.0515(9) Uani 1 1 d . . . C21 C 0.6204(7) 0.76003(19) 0.2798(3) 0.0706(11) Uani 1 1 d . . . H15 H 0.4959 0.7829 0.2867 0.085 Uiso 1 1 calc R . . C12 C 1.2117(5) 0.60754(16) 0.5037(2) 0.0515(9) Uani 1 1 d . . . H16 H 1.3073 0.6286 0.5525 0.062 Uiso 1 1 calc R . . C7 C 1.0052(5) 0.55852(17) 0.6229(3) 0.0558(9) Uani 1 1 d . . . C8 C 0.9999(6) 0.5148(2) 0.6982(3) 0.0736(12) Uani 1 1 d . . . H18 H 1.0848 0.4801 0.6938 0.088 Uiso 1 1 calc R . . C9 C 0.8677(7) 0.5229(3) 0.7801(3) 0.0870(15) Uani 1 1 d . . . H19 H 0.8655 0.4931 0.8305 0.104 Uiso 1 1 calc R . . C17 C 1.4933(6) 0.57198(18) 0.3736(3) 0.0641(11) Uani 1 1 d . . . H21 H 1.5830 0.5459 0.4107 0.077 Uiso 1 1 calc R . . B1 B 0.6659(8) 0.7393(2) 0.4706(4) 0.0635(12) Uani 1 1 d . . . C3 C 0.3965(10) 0.5883(5) 0.8742(6) 0.208(4) Uani 1 1 d . . . H23A H 0.3560 0.5867 0.8032 0.313 Uiso 1 1 calc R . . H23B H 0.3473 0.6259 0.9028 0.313 Uiso 1 1 calc R . . H23C H 0.3325 0.5548 0.9092 0.313 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 F1 0.0771(16) 0.134(2) 0.0674(16) 0.0019(14) 0.0142(12) 0.0453(15) F2 0.1101(19) 0.0766(16) 0.0661(15) -0.0125(12) -0.0036(13) -0.0020(14) O1 0.0500(14) 0.0846(19) 0.0487(14) -0.0008(13) 0.0097(11) 0.0056(13) O2 0.0666(15) 0.0617(16) 0.0538(15) 0.0090(12) 0.0143(12) -0.0006(12) N1 0.0563(17) 0.0648(19) 0.0485(18) -0.0015(14) 0.0021(14) 0.0080(15) N2 0.0514(16) 0.0646(19) 0.0482(18) 0.0024(14) 0.0099(14) 0.0031(15) C1 0.131(5) 0.205(7) 0.067(3) -0.012(4) 0.018(3) -0.008(5) C2 0.081(3) 0.324(11) 0.050(3) 0.038(5) 0.022(2) 0.017(5) C4 0.060(2) 0.139(4) 0.046(2) 0.015(3) 0.0083(19) -0.006(3) C5 0.053(2) 0.106(3) 0.046(2) -0.003(2) 0.0049(17) -0.005(2) C6 0.048(2) 0.079(3) 0.041(2) 0.0004(18) 0.0036(16) -0.0137(19) C10 0.0447(19) 0.064(2) 0.043(2) -0.0060(16) -0.0007(15) -0.0055(17) C11 0.0450(18) 0.053(2) 0.043(2) -0.0011(15) 0.0044(15) -0.0052(15) C13 0.0482(18) 0.051(2) 0.045(2) -0.0039(16) 0.0057(15) -0.0081(16) C14 0.0497(19) 0.059(2) 0.046(2) 0.0044(16) 0.0074(16) -0.0020(16) C15 0.067(2) 0.069(3) 0.052(2) 0.0045(19) 0.0172(19) 0.005(2) C16 0.068(2) 0.078(3) 0.059(2) 0.001(2) 0.0213(19) 0.011(2) C20 0.075(3) 0.086(3) 0.054(3) 0.019(2) 0.001(2) 0.005(2) C19 0.065(2) 0.066(2) 0.047(2) 0.0069(17) 0.0093(17) 0.0033(19) C18 0.052(2) 0.056(2) 0.046(2) 0.0006(17) 0.0054(16) -0.0010(17) C21 0.065(2) 0.084(3) 0.063(3) 0.007(2) 0.001(2) 0.018(2) C12 0.0496(19) 0.061(2) 0.044(2) 0.0005(16) 0.0085(15) -0.0058(16) C7 0.054(2) 0.068(2) 0.046(2) 0.0046(17) 0.0060(17) -0.0100(18) C8 0.074(3) 0.090(3) 0.058(2) 0.018(2) 0.009(2) -0.007(2) C9 0.071(3) 0.131(4) 0.060(3) 0.036(3) 0.003(2) -0.018(3) C17 0.055(2) 0.074(3) 0.063(3) 0.0005(19) 0.0124(18) 0.0127(19) B1 0.060(3) 0.074(3) 0.056(3) -0.007(2) 0.004(2) 0.015(2) C3 0.084(4) 0.393(13) 0.150(7) -0.120(8) 0.047(4) -0.004(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 F1 B1 1.373(5) . ? F2 B1 1.376(5) . ? O1 C10 1.317(4) . ? O1 B1 1.468(5) . ? O2 C7 1.380(4) . ? O2 C12 1.427(4) . ? N1 C21 1.339(5) . ? N1 C18 1.400(4) . ? N1 B1 1.552(5) . ? N2 C17 1.346(4) . ? N2 C14 1.389(4) . ? N2 C12 1.442(4) . ? C1 C2 1.466(8) . ? C1 H1A 0.9602 . ? C1 H1B 0.9602 . ? C1 H1C 0.9602 . ? C2 C3 1.308(8) . ? C2 C4 1.518(7) . ? C2 H2 0.9800 . ? C4 C5 1.384(6) . ? C4 C9 1.387(7) . ? C5 C6 1.388(5) . ? C5 H4 0.9300 . ? C6 C7 1.405(5) . ? C6 C10 1.457(5) . ? C10 C11 1.360(4) . ? C11 C13 1.416(4) . ? C11 C12 1.507(5) . ? C13 C18 1.392(5) . ? C13 C14 1.434(5) . ? C14 C15 1.377(5) . ? C15 C16 1.399(5) . ? C15 H10 0.9300 . ? C16 C17 1.370(5) . ? C16 H11 0.9300 . ? C20 C19 1.364(5) . ? C20 C21 1.385(6) . ? C20 H12 0.9300 . ? C19 C18 1.397(5) . ? C19 H13 0.9300 . ? C21 H15 0.9300 . ? C12 H16 0.9800 . ? C7 C8 1.378(5) . ? C8 C9 1.379(6) . ? C8 H18 0.9300 . ? C9 H19 0.9300 . ? C17 H21 0.9300 . ? C3 H23A 0.9600 . ? C3 H23B 0.9600 . ? C3 H23C 0.9600 . ? 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 C10 O1 B1 124.5(3) . . ? C7 O2 C12 110.9(3) . . ? C21 N1 C18 106.3(3) . . ? C21 N1 B1 123.9(3) . . ? C18 N1 B1 129.4(3) . . ? C17 N2 C14 109.8(3) . . ? C17 N2 C12 137.1(3) . . ? C14 N2 C12 112.3(3) . . ? C2 C1 H1A 108.0 . . ? C2 C1 H1B 112.2 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 108.2 . . ? H1A C1 H1C 109.4 . . ? H1B C1 H1C 109.5 . . ? C3 C2 C1 127.7(6) . . ? C3 C2 C4 118.9(5) . . ? C1 C2 C4 113.4(4) . . ? C3 C2 H2 92.2 . . ? C1 C2 H2 89.0 . . ? C4 C2 H2 89.0 . . ? C5 C4 C9 117.1(4) . . ? C5 C4 C2 120.5(5) . . ? C9 C4 C2 122.3(5) . . ? C4 C5 C6 122.1(4) . . ? C4 C5 H4 119.0 . . ? C6 C5 H4 118.9 . . ? C5 C6 C7 118.8(3) . . ? C5 C6 C10 123.4(4) . . ? C7 C6 C10 117.7(3) . . ? O1 C10 C11 126.2(3) . . ? O1 C10 C6 115.9(3) . . ? C11 C10 C6 117.7(3) . . ? C10 C11 C13 132.2(3) . . ? C10 C11 C12 116.6(3) . . ? C13 C11 C12 110.1(3) . . ? C18 C13 C11 128.1(3) . . ? C18 C13 C14 124.9(3) . . ? C11 C13 C14 106.8(3) . . ? C15 C14 N2 107.0(3) . . ? C15 C14 C13 144.4(3) . . ? N2 C14 C13 108.5(3) . . ? C14 C15 C16 106.9(3) . . ? C14 C15 H10 126.4 . . ? C16 C15 H10 126.7 . . ? C17 C16 C15 108.6(3) . . ? C17 C16 H11 125.6 . . ? C15 C16 H11 125.8 . . ? C19 C20 C21 106.8(4) . . ? C19 C20 H12 126.4 . . ? C21 C20 H12 126.8 . . ? C20 C19 C18 107.8(3) . . ? C20 C19 H13 126.1 . . ? C18 C19 H13 126.1 . . ? C19 C18 N1 108.0(3) . . ? C19 C18 C13 129.2(3) . . ? N1 C18 C13 122.6(3) . . ? N1 C21 C20 111.1(4) . . ? N1 C21 H15 124.6 . . ? C20 C21 H15 124.3 . . ? O2 C12 N2 110.6(3) . . ? O2 C12 C11 112.0(3) . . ? N2 C12 C11 101.6(3) . . ? O2 C12 H16 110.6 . . ? N2 C12 H16 110.8 . . ? C11 C12 H16 110.8 . . ? O2 C7 C8 118.4(4) . . ? O2 C7 C6 121.8(3) . . ? C8 C7 C6 119.8(3) . . ? C7 C8 C9 119.6(4) . . ? C7 C8 H18 120.1 . . ? C9 C8 H18 120.3 . . ? C8 C9 C4 122.3(4) . . ? C8 C9 H19 118.8 . . ? C4 C9 H19 118.8 . . ? N2 C17 C16 107.6(3) . . ? N2 C17 H21 126.1 . . ? C16 C17 H21 126.4 . . ? F1 B1 F2 112.0(4) . . ? F1 B1 O1 106.0(4) . . ? F2 B1 O1 108.2(3) . . ? F1 B1 N1 107.7(3) . . ? F2 B1 N1 109.6(4) . . ? O1 B1 N1 113.3(3) . . ? C2 C3 H23A 110.3 . . ? C2 C3 H23B 109.5 . . ? H23A C3 H23B 109.5 . . ? C2 C3 H23C 108.6 . . ? H23A C3 H23C 109.5 . . ? H23B C3 H23C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 23.28 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.393 _refine_diff_density_min -0.325 _refine_diff_density_rms 0.079 ##########################################END data_6 _database_code_depnum_ccdc_archive 'CCDC 873217' #TrackingRef 'CIF-all.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C21 H18 N2 O2' _chemical_formula_sum 'C21 H18 N2 O2' _chemical_melting_point ? _exptl_crystal_description Block _exptl_crystal_colour Brown _diffrn_ambient_temperature 293(2) _chemical_formula_weight 330.37 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' _symmetry_int_tables_number 2 _chemical_absolute_configuration ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.2128(9) _cell_length_b 9.6112(7) _cell_length_c 10.0583(6) _cell_angle_alpha 77.842(6) _cell_angle_beta 71.347(7) _cell_angle_gamma 88.204(7) _cell_volume 824.29(11) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3956 _cell_measurement_theta_min 3.12 _cell_measurement_theta_max 32.38 _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.331 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 348 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_radiation_probe ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OXFORD DIFFRACTION XCALIBUR-S' _diffrn_measurement_method \w/q-scan _diffrn_detector_area_resol_mean 15.9948 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% <3%> _diffrn_reflns_number 9214 _diffrn_reflns_av_R_equivalents 0.0164 _diffrn_reflns_av_sigmaI/netI 0.0300 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.13 _diffrn_reflns_theta_max 32.46 _reflns_number_total 5943 _reflns_number_gt 4091 _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^)+(0.0533P)^2^+0.2798P] 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 5311 _refine_ls_number_parameters 230 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0695 _refine_ls_R_factor_gt 0.0539 _refine_ls_wR_factor_ref 0.1564 _refine_ls_wR_factor_gt 0.1445 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _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 H21 H 0.091(3) 0.641(3) -0.017(2) 0.079(7) Uiso 1 1 d . . . O2 O 0.30888(13) 0.43253(12) 0.39927(11) 0.0437(3) Uani 1 1 d . . . C6 C 0.07094(16) 0.37010(14) 0.36464(15) 0.0357(3) Uani 1 1 d . . . O1 O 0.01983(12) 0.48501(12) 0.15192(12) 0.0465(3) Uani 1 1 d . . . C10 C 0.26855(15) 0.52014(14) 0.16768(14) 0.0339(3) Uani 1 1 d . . . N1 N 0.50406(14) 0.54939(14) 0.19300(14) 0.0407(3) Uani 1 1 d . . . C13 C 0.48655(16) 0.66135(15) 0.08962(15) 0.0371(3) Uani 1 1 d . . . C21 C 0.11390(16) 0.46063(14) 0.21778(15) 0.0349(3) Uani 1 1 d . . . C5 C -0.07322(18) 0.29966(15) 0.42502(16) 0.0403(3) Uani 1 1 d . . . H5 H -0.1367 0.3036 0.3688 0.048 Uiso 1 1 calc R . . N2 N 0.14615(15) 0.72597(15) -0.04907(14) 0.0426(3) Uani 1 1 d . . . C17 C 0.27726(16) 0.74823(15) -0.01778(15) 0.0360(3) Uani 1 1 d . . . C14 C 0.33618(15) 0.64433(14) 0.07426(14) 0.0335(3) Uani 1 1 d . . . C7 C 0.16614(17) 0.36480(15) 0.44963(15) 0.0383(3) Uani 1 1 d . . . C4 C -0.12429(19) 0.22421(16) 0.56616(16) 0.0436(3) Uani 1 1 d . . . C11 C 0.37512(17) 0.44989(15) 0.24699(16) 0.0382(3) Uani 1 1 d . . . H11 H 0.4059 0.3579 0.2215 0.046 Uiso 1 1 calc R . . C9 C -0.0267(2) 0.22442(18) 0.64850(16) 0.0495(4) Uani 1 1 d . . . H9 H -0.0593 0.1765 0.7441 0.059 Uiso 1 1 calc R . . C8 C 0.1155(2) 0.29313(17) 0.59266(17) 0.0472(4) Uani 1 1 d . . . H8 H 0.1773 0.2916 0.6501 0.057 Uiso 1 1 calc R . . C12 C 0.62124(17) 0.74268(19) 0.03543(18) 0.0455(4) Uani 1 1 d . . . H12 H 0.6427 0.8255 -0.0358 0.055 Uiso 1 1 calc R . . C3 C -0.2765(2) 0.14067(18) 0.62913(18) 0.0525(4) Uani 1 1 d . . . H3 H -0.3168 0.1446 0.7310 0.063 Uiso 1 1 calc R . . C20 C 0.1165(2) 0.84442(19) -0.1335(2) 0.0528(4) Uani 1 1 d . . . H20 H 0.0342 0.8552 -0.1690 0.063 Uiso 1 1 calc R . . C16 C 0.64763(18) 0.5559(2) 0.20394(19) 0.0498(4) Uani 1 1 d . . . H16 H 0.6877 0.4912 0.2645 0.060 Uiso 1 1 calc R . . C15 C 0.72085(19) 0.6754(2) 0.10939(19) 0.0527(4) Uani 1 1 d . . . H15 H 0.8198 0.7075 0.0956 0.063 Uiso 1 1 calc R . . C18 C 0.3301(2) 0.88649(18) -0.0865(2) 0.0519(4) Uani 1 1 d . . . H18 H 0.4175 0.9313 -0.0853 0.062 Uiso 1 1 calc R . . C19 C 0.2283(2) 0.9463(2) -0.1581(2) 0.0615(5) Uani 1 1 d . . . H19 H 0.2351 1.0385 -0.2124 0.074 Uiso 1 1 calc R . . C2 C -0.2507(3) -0.0154(2) 0.6211(3) 0.0860(8) Uani 1 1 d . . . H2A H -0.1748 -0.0509 0.6651 0.129 Uiso 1 1 calc R . . H2B H -0.2161 -0.0235 0.5225 0.129 Uiso 1 1 calc R . . H2C H -0.3452 -0.0700 0.6708 0.129 Uiso 1 1 calc R . . C1 C -0.3968(2) 0.1989(3) 0.5610(3) 0.0745(6) Uani 1 1 d . . . H1A H -0.4896 0.1412 0.6068 0.112 Uiso 1 1 calc R . . H1B H -0.3603 0.1973 0.4607 0.112 Uiso 1 1 calc R . . H1C H -0.4166 0.2951 0.5724 0.112 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 O2 0.0440(6) 0.0514(6) 0.0398(5) -0.0075(5) -0.0198(5) -0.0023(5) C6 0.0388(7) 0.0323(6) 0.0350(6) -0.0058(5) -0.0114(5) 0.0011(5) O1 0.0386(6) 0.0547(6) 0.0459(6) 0.0037(5) -0.0212(5) -0.0109(5) C10 0.0320(6) 0.0364(6) 0.0350(6) -0.0063(5) -0.0135(5) -0.0009(5) N1 0.0316(6) 0.0466(7) 0.0474(7) -0.0104(5) -0.0171(5) 0.0017(5) C13 0.0319(7) 0.0414(7) 0.0399(7) -0.0121(6) -0.0118(5) 0.0002(5) C21 0.0339(7) 0.0353(6) 0.0366(7) -0.0063(5) -0.0133(5) -0.0018(5) C5 0.0409(8) 0.0374(7) 0.0394(7) -0.0062(6) -0.0093(6) -0.0012(6) N2 0.0380(7) 0.0419(7) 0.0473(7) -0.0004(5) -0.0180(5) -0.0037(5) C17 0.0322(6) 0.0371(7) 0.0372(7) -0.0064(5) -0.0095(5) -0.0015(5) C14 0.0301(6) 0.0368(6) 0.0344(6) -0.0103(5) -0.0094(5) 0.0002(5) C7 0.0426(8) 0.0349(6) 0.0385(7) -0.0078(5) -0.0145(6) 0.0028(5) C4 0.0471(8) 0.0351(7) 0.0398(7) -0.0081(6) -0.0020(6) 0.0013(6) C11 0.0376(7) 0.0385(7) 0.0417(7) -0.0092(6) -0.0166(6) 0.0021(5) C9 0.0644(11) 0.0453(8) 0.0320(7) -0.0050(6) -0.0083(7) 0.0037(7) C8 0.0608(10) 0.0465(8) 0.0366(7) -0.0080(6) -0.0195(7) 0.0047(7) C12 0.0342(7) 0.0552(9) 0.0466(8) -0.0145(7) -0.0092(6) -0.0061(6) C3 0.0525(10) 0.0446(8) 0.0449(8) -0.0069(7) 0.0048(7) -0.0050(7) C20 0.0514(10) 0.0515(9) 0.0550(10) 0.0017(7) -0.0246(8) 0.0033(7) C16 0.0341(8) 0.0666(11) 0.0566(9) -0.0191(8) -0.0221(7) 0.0075(7) C15 0.0307(7) 0.0756(12) 0.0558(10) -0.0212(9) -0.0143(7) -0.0036(7) C18 0.0478(9) 0.0413(8) 0.0625(10) 0.0008(7) -0.0185(8) -0.0085(7) C19 0.0640(12) 0.0442(9) 0.0690(12) 0.0116(8) -0.0256(9) -0.0036(8) C2 0.0784(16) 0.0419(10) 0.1082(19) -0.0072(11) 0.0060(13) -0.0109(10) C1 0.0492(11) 0.0693(13) 0.0886(15) -0.0066(11) -0.0048(10) -0.0124(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O2 C7 1.3778(18) . ? O2 C11 1.4307(18) . ? C6 C5 1.399(2) . ? C6 C7 1.400(2) . ? C6 C21 1.4839(19) . ? O1 C21 1.2385(17) . ? C10 C14 1.3768(19) . ? C10 C21 1.4428(18) . ? C10 C11 1.5128(19) . ? N1 C16 1.3663(19) . ? N1 C13 1.3749(19) . ? N1 C11 1.4355(18) . ? C13 C12 1.377(2) . ? C13 C14 1.4600(19) . ? C5 C4 1.387(2) . ? C5 H5 0.9300 . ? N2 C20 1.346(2) . ? N2 C17 1.3753(18) . ? N2 H21 0.91(2) . ? C17 C18 1.385(2) . ? C17 C14 1.431(2) . ? C7 C8 1.391(2) . ? C4 C9 1.404(2) . ? C4 C3 1.517(2) . ? C11 H11 0.9800 . ? C9 C8 1.377(2) . ? C9 H9 0.9300 . ? C8 H8 0.9300 . ? C12 C15 1.418(2) . ? C12 H12 0.9300 . ? C3 C1 1.515(3) . ? C3 C2 1.526(3) . ? C3 H3 0.9800 . ? C20 C19 1.371(3) . ? C20 H20 0.9300 . ? C16 C15 1.362(3) . ? C16 H16 0.9300 . ? C15 H15 0.9300 . ? C18 C19 1.397(3) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? 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 C7 O2 C11 111.90(11) . . ? C5 C6 C7 118.96(13) . . ? C5 C6 C21 119.75(13) . . ? C7 C6 C21 121.00(13) . . ? C14 C10 C21 132.42(13) . . ? C14 C10 C11 110.29(12) . . ? C21 C10 C11 116.42(12) . . ? C16 N1 C13 110.25(14) . . ? C16 N1 C11 137.27(14) . . ? C13 N1 C11 111.95(12) . . ? N1 C13 C12 107.41(13) . . ? N1 C13 C14 108.34(12) . . ? C12 C13 C14 144.14(15) . . ? O1 C21 C10 125.55(13) . . ? O1 C21 C6 121.13(13) . . ? C10 C21 C6 113.24(12) . . ? C4 C5 C6 122.01(15) . . ? C4 C5 H5 119.0 . . ? C6 C5 H5 119.0 . . ? C20 N2 C17 109.91(14) . . ? C20 N2 H21 127.0(15) . . ? C17 N2 H21 123.1(15) . . ? N2 C17 C18 106.69(13) . . ? N2 C17 C14 123.54(12) . . ? C18 C17 C14 129.73(14) . . ? C10 C14 C17 130.18(13) . . ? C10 C14 C13 107.05(12) . . ? C17 C14 C13 122.67(12) . . ? O2 C7 C8 117.23(14) . . ? O2 C7 C6 122.72(13) . . ? C8 C7 C6 120.01(14) . . ? C5 C4 C9 117.15(15) . . ? C5 C4 C3 122.05(16) . . ? C9 C4 C3 120.76(14) . . ? O2 C11 N1 110.68(11) . . ? O2 C11 C10 112.34(12) . . ? N1 C11 C10 102.29(11) . . ? O2 C11 H11 110.4 . . ? N1 C11 H11 110.4 . . ? C10 C11 H11 110.4 . . ? C8 C9 C4 122.31(14) . . ? C8 C9 H9 118.8 . . ? C4 C9 H9 118.8 . . ? C9 C8 C7 119.52(15) . . ? C9 C8 H8 120.2 . . ? C7 C8 H8 120.2 . . ? C13 C12 C15 106.57(15) . . ? C13 C12 H12 126.7 . . ? C15 C12 H12 126.7 . . ? C1 C3 C4 114.34(15) . . ? C1 C3 C2 110.44(19) . . ? C4 C3 C2 109.66(15) . . ? C1 C3 H3 107.4 . . ? C4 C3 H3 107.4 . . ? C2 C3 H3 107.4 . . ? N2 C20 C19 108.29(16) . . ? N2 C20 H20 125.9 . . ? C19 C20 H20 125.9 . . ? C15 C16 N1 107.00(15) . . ? C15 C16 H16 126.5 . . ? N1 C16 H16 126.5 . . ? C16 C15 C12 108.75(14) . . ? C16 C15 H15 125.6 . . ? C12 C15 H15 125.6 . . ? C17 C18 C19 107.60(15) . . ? C17 C18 H18 126.2 . . ? C19 C18 H18 126.2 . . ? C20 C19 C18 107.50(15) . . ? C20 C19 H19 126.2 . . ? C18 C19 H19 126.2 . . ? C3 C2 H2A 109.5 . . ? C3 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C3 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C3 C1 H1A 109.5 . . ? C3 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C3 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? 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 C16 N1 C13 C12 -1.18(17) . . . . ? C11 N1 C13 C12 -174.36(12) . . . . ? C16 N1 C13 C14 175.90(12) . . . . ? C11 N1 C13 C14 2.72(16) . . . . ? C14 C10 C21 O1 26.2(3) . . . . ? C11 C10 C21 O1 -165.69(14) . . . . ? C14 C10 C21 C6 -150.35(15) . . . . ? C11 C10 C21 C6 17.73(18) . . . . ? C5 C6 C21 O1 6.2(2) . . . . ? C7 C6 C21 O1 -167.45(14) . . . . ? C5 C6 C21 C10 -177.01(12) . . . . ? C7 C6 C21 C10 9.31(19) . . . . ? C7 C6 C5 C4 -0.3(2) . . . . ? C21 C6 C5 C4 -174.14(14) . . . . ? C20 N2 C17 C18 -0.15(19) . . . . ? C20 N2 C17 C14 177.54(15) . . . . ? C21 C10 C14 C17 -8.5(3) . . . . ? C11 C10 C14 C17 -177.12(14) . . . . ? C21 C10 C14 C13 167.88(14) . . . . ? C11 C10 C14 C13 -0.74(15) . . . . ? N2 C17 C14 C10 -13.4(2) . . . . ? C18 C17 C14 C10 163.76(17) . . . . ? N2 C17 C14 C13 170.74(13) . . . . ? C18 C17 C14 C13 -12.1(2) . . . . ? N1 C13 C14 C10 -1.15(16) . . . . ? C12 C13 C14 C10 174.1(2) . . . . ? N1 C13 C14 C17 175.57(12) . . . . ? C12 C13 C14 C17 -9.2(3) . . . . ? C11 O2 C7 C8 155.73(14) . . . . ? C11 O2 C7 C6 -26.52(19) . . . . ? C5 C6 C7 O2 -179.19(13) . . . . ? C21 C6 C7 O2 -5.5(2) . . . . ? C5 C6 C7 C8 -1.5(2) . . . . ? C21 C6 C7 C8 172.24(14) . . . . ? C6 C5 C4 C9 1.8(2) . . . . ? C6 C5 C4 C3 -176.33(14) . . . . ? C7 O2 C11 N1 165.98(12) . . . . ? C7 O2 C11 C10 52.34(16) . . . . ? C16 N1 C11 O2 66.6(2) . . . . ? C13 N1 C11 O2 -122.86(13) . . . . ? C16 N1 C11 C10 -173.54(17) . . . . ? C13 N1 C11 C10 -2.99(16) . . . . ? C14 C10 C11 O2 120.93(13) . . . . ? C21 C10 C11 O2 -49.71(17) . . . . ? C14 C10 C11 N1 2.23(15) . . . . ? C21 C10 C11 N1 -168.41(12) . . . . ? C5 C4 C9 C8 -1.5(2) . . . . ? C3 C4 C9 C8 176.66(15) . . . . ? C4 C9 C8 C7 -0.3(3) . . . . ? O2 C7 C8 C9 179.61(14) . . . . ? C6 C7 C8 C9 1.8(2) . . . . ? N1 C13 C12 C15 0.26(17) . . . . ? C14 C13 C12 C15 -175.00(19) . . . . ? C5 C4 C3 C1 -28.4(2) . . . . ? C9 C4 C3 C1 153.58(17) . . . . ? C5 C4 C3 C2 96.3(2) . . . . ? C9 C4 C3 C2 -81.8(2) . . . . ? C17 N2 C20 C19 -0.2(2) . . . . ? C13 N1 C16 C15 1.64(19) . . . . ? C11 N1 C16 C15 172.29(17) . . . . ? N1 C16 C15 C12 -1.4(2) . . . . ? C13 C12 C15 C16 0.74(19) . . . . ? N2 C17 C18 C19 0.4(2) . . . . ? C14 C17 C18 C19 -177.06(16) . . . . ? N2 C20 C19 C18 0.5(2) . . . . ? C17 C18 C19 C20 -0.6(2) . . . . ? _diffrn_measured_fraction_theta_max 0.894 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.258 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.041