# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # 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_TBPO-pnba _audit_creation_date 2012-10-10 _audit_creation_method ; Olex2 1.2 (compiled 2012.05.09 svn.r2324, GUI svn.r4230) ; _chemical_name_common 'TBPO.4-nitrobenzoic acid' _chemical_name_systematic ; ? ; _chemical_formula_moiety '2(C7 H5 N O4), C13 H14 N2 O' _chemical_formula_sum 'C27 H24 N4 O9' _chemical_formula_weight 548.50 _chemical_melting_point ? 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' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 7.3410(5) _cell_length_b 7.4478(4) _cell_length_c 24.440(3) _cell_angle_alpha 96.237(7) _cell_angle_beta 90.714(7) _cell_angle_gamma 103.836(5) _cell_volume 1288.74(18) _cell_formula_units_Z 2 _cell_measurement_reflns_used 1921 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 29.2432 _cell_measurement_theta_min 2.8301 _exptl_absorpt_coefficient_mu 0.108 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.84591 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour yellowish _exptl_crystal_density_diffrn 1.413 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 572 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.31 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0431 _diffrn_reflns_av_unetI/netI 0.0945 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 8730 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 2.84 _diffrn_ambient_temperature 298(2) _diffrn_detector_area_resol_mean 15.9821 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -9.00 85.00 1.0000 75.0000 omega____ theta____ kappa____ phi______ frames - 18.9022 77.0000 30.0000 94 #__ type_ start__ end____ width___ exp.time_ 2 omega -46.00 45.00 1.0000 75.0000 omega____ theta____ kappa____ phi______ frames - 18.9022 -77.0000 120.0000 91 #__ type_ start__ end____ width___ exp.time_ 3 omega -6.00 89.00 1.0000 75.0000 omega____ theta____ kappa____ phi______ frames - 18.9022 37.0000 30.0000 95 #__ type_ start__ end____ width___ exp.time_ 4 omega -11.00 88.00 1.0000 75.0000 omega____ theta____ kappa____ phi______ frames - 18.9022 77.0000 -120.0000 99 ; _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0266604000 _diffrn_orient_matrix_UB_12 0.0984494000 _diffrn_orient_matrix_UB_13 0.0012472000 _diffrn_orient_matrix_UB_21 0.0006046000 _diffrn_orient_matrix_UB_22 0.0072236000 _diffrn_orient_matrix_UB_23 0.0291879000 _diffrn_orient_matrix_UB_31 0.0959682000 _diffrn_orient_matrix_UB_32 -0.0026030000 _diffrn_orient_matrix_UB_33 0.0006741000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 1977 _reflns_number_total 4533 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; SHELXS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.163 _refine_diff_density_min -0.159 _refine_diff_density_rms 0.040 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.972 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 369 _refine_ls_number_reflns 4533 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1540 _refine_ls_R_factor_gt 0.0569 _refine_ls_restrained_S_all 0.972 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0385P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1024 _refine_ls_wR_factor_ref 0.1421 _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. DFIX 0.85 0.01 O6 H6 O1 H1 ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.0645(3) 0.1029(3) 0.92526(11) 0.0671(8) Uani 1 1 d D . . O5 O 0.8321(3) 1.0224(3) 0.84392(10) 0.0685(8) Uani 1 1 d . . . N2 N 0.7534(4) 0.8435(4) 0.82838(12) 0.0525(8) Uani 1 1 d . . . O2 O 0.2641(3) -0.0165(3) 0.87359(12) 0.0715(8) Uani 1 1 d . . . O4 O 0.9692(4) 0.4178(4) 1.06589(12) 0.0854(10) Uani 1 1 d . . . C14 C 0.3340(4) 0.2461(4) 1.00821(16) 0.0517(10) Uani 1 1 d . . . H14 H 0.2094 0.2428 1.0156 0.062 Uiso 1 1 calc R . . C16 C 0.4902(4) 0.6130(4) 0.79134(15) 0.0564(10) Uani 1 1 d . . . H16 H 0.3675 0.5828 0.7768 0.068 Uiso 1 1 calc R . . C11 C 0.7042(4) 0.2556(4) 0.98584(16) 0.0532(10) Uani 1 1 d . . . H11 H 0.8290 0.2590 0.9787 0.064 Uiso 1 1 calc R . . C12 C 0.6571(5) 0.3347(4) 1.03512(16) 0.0501(10) Uani 1 1 d . . . C8 C 0.2308(5) 0.0751(4) 0.91500(17) 0.0555(10) Uani 1 1 d . . . C9 C 0.3778(4) 0.1661(4) 0.95832(16) 0.0483(9) Uani 1 1 d . . . O3 O 0.7683(4) 0.5098(4) 1.11828(13) 0.0873(10) Uani 1 1 d . . . C15 C 0.5739(4) 0.7941(4) 0.80918(15) 0.0570(10) Uani 1 1 d . . . H15 H 0.5062 0.8845 0.8081 0.068 Uiso 1 1 calc R . . C10 C 0.5636(4) 0.1710(4) 0.94708(15) 0.0530(10) Uani 1 1 d . . . H10 H 0.5932 0.1169 0.9133 0.064 Uiso 1 1 calc R . . N1 N 0.8085(5) 0.4260(4) 1.07642(15) 0.0616(9) Uani 1 1 d . . . C17 C 0.5823(4) 0.4737(4) 0.79420(14) 0.0486(9) Uani 1 1 d . . . C19 C 0.8487(5) 0.7123(4) 0.83077(15) 0.0598(11) Uani 1 1 d . . . H19 H 0.9736 0.7467 0.8434 0.072 Uiso 1 1 calc R . . C18 C 0.7662(4) 0.5279(4) 0.81492(15) 0.0579(10) Uani 1 1 d . . . H18 H 0.8341 0.4387 0.8181 0.069 Uiso 1 1 calc R . . C13 C 0.4739(4) 0.3312(4) 1.04738(15) 0.0522(10) Uani 1 1 d . . . H13 H 0.4450 0.3850 1.0813 0.063 Uiso 1 1 calc R . . C23 C 0.0765(5) -0.0123(4) 0.68291(18) 0.0578(10) Uani 1 1 d . . . N3 N -0.2337(4) -0.0858(4) 0.60950(16) 0.0712(10) Uani 1 1 d . . . C20 C 0.4926(4) 0.2714(4) 0.77801(16) 0.0639(11) Uani 1 1 d . . . H20A H 0.4586 0.2132 0.8113 0.077 Uiso 1 1 calc R . . H20B H 0.5853 0.2139 0.7603 0.077 Uiso 1 1 calc R . . C24 C 0.0952(5) -0.0408(5) 0.62735(19) 0.0715(12) Uani 1 1 d . . . H24 H 0.2131 -0.0364 0.6132 0.086 Uiso 1 1 calc R . . C22 C 0.2393(5) 0.0253(4) 0.72338(16) 0.0713(12) Uani 1 1 d . . . H22A H 0.3365 -0.0294 0.7073 0.086 Uiso 1 1 calc R . . H22B H 0.1989 -0.0344 0.7560 0.086 Uiso 1 1 calc R . . C21 C 0.3203(4) 0.2295(4) 0.74003(16) 0.0659(11) Uani 1 1 d . . . H21A H 0.2250 0.2822 0.7582 0.079 Uiso 1 1 calc R . . H21B H 0.3524 0.2903 0.7071 0.079 Uiso 1 1 calc R . . C26 C -0.0994(5) -0.0161(5) 0.70054(17) 0.0778(13) Uani 1 1 d . . . H26 H -0.1186 0.0074 0.7379 0.093 Uiso 1 1 calc R . . C25 C -0.0626(6) -0.0766(5) 0.59187(17) 0.0736(12) Uani 1 1 d . . . H25 H -0.0468 -0.0947 0.5541 0.088 Uiso 1 1 calc R . . C27 C -0.2492(6) -0.0548(5) 0.6630(2) 0.0847(13) Uani 1 1 d . . . H27 H -0.3681 -0.0593 0.6762 0.102 Uiso 1 1 calc R . . C2 C 0.6380(5) 0.3186(4) 0.54906(17) 0.0561(10) Uani 1 1 d . . . O8 O 1.2422(4) 0.5590(4) 0.65231(13) 0.0907(10) Uani 1 1 d . . . N4 N 1.0813(5) 0.5255(4) 0.66749(16) 0.0670(10) Uani 1 1 d . . . O7 O 0.3176(4) 0.2405(4) 0.52045(12) 0.1008(11) Uani 1 1 d . . . O6 O 0.5253(4) 0.1895(4) 0.45983(14) 0.0834(9) Uani 1 1 d D . . C5 C 0.9274(5) 0.4532(4) 0.62636(17) 0.0544(10) Uani 1 1 d . . . O9 O 1.0424(4) 0.5496(4) 0.71562(13) 0.0928(10) Uani 1 1 d . . . C3 C 0.8211(5) 0.3246(4) 0.53529(16) 0.0681(11) Uani 1 1 d . . . H3 H 0.8468 0.2825 0.4997 0.082 Uiso 1 1 calc R . . C6 C 0.7472(5) 0.4482(5) 0.64108(16) 0.0681(11) Uani 1 1 d . . . H6A H 0.7220 0.4892 0.6769 0.082 Uiso 1 1 calc R . . C1 C 0.4779(6) 0.2470(5) 0.50851(18) 0.0674(11) Uani 1 1 d . . . C4 C 0.9668(5) 0.3932(5) 0.57441(17) 0.0678(11) Uani 1 1 d . . . H4 H 1.0903 0.3980 0.5651 0.081 Uiso 1 1 calc R . . C7 C 0.6036(5) 0.3813(5) 0.60172(18) 0.0722(12) Uani 1 1 d . . . H7 H 0.4807 0.3787 0.6112 0.087 Uiso 1 1 calc R . . H1 H -0.011(4) 0.066(4) 0.8968(9) 0.075(13) Uiso 1 1 d D . . H6 H 0.432(5) 0.161(6) 0.4368(17) 0.16(2) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0486(16) 0.0784(17) 0.072(2) -0.0132(15) -0.0036(16) 0.0208(14) O5 0.0675(16) 0.0476(13) 0.085(2) -0.0074(13) -0.0142(15) 0.0105(12) N2 0.0466(18) 0.0515(17) 0.060(2) 0.0032(15) -0.0019(15) 0.0150(15) O2 0.0546(15) 0.0782(17) 0.076(2) -0.0199(15) -0.0006(15) 0.0185(13) O4 0.0525(16) 0.105(2) 0.097(3) 0.0047(17) -0.0089(17) 0.0190(16) C14 0.042(2) 0.0463(19) 0.068(3) 0.0093(19) 0.004(2) 0.0107(17) C16 0.046(2) 0.055(2) 0.070(3) 0.0081(19) -0.0059(19) 0.0145(19) C11 0.042(2) 0.054(2) 0.066(3) 0.012(2) 0.002(2) 0.0147(17) C12 0.048(2) 0.0410(19) 0.058(3) 0.0092(18) -0.004(2) 0.0036(18) C8 0.046(2) 0.049(2) 0.069(3) 0.005(2) 0.006(2) 0.0079(19) C9 0.045(2) 0.0389(18) 0.062(3) 0.0055(17) 0.0069(19) 0.0120(16) O3 0.079(2) 0.096(2) 0.070(2) -0.0150(17) -0.0018(18) 0.0007(16) C15 0.051(2) 0.056(2) 0.069(3) 0.0077(19) -0.006(2) 0.0213(18) C10 0.051(2) 0.0500(19) 0.059(3) -0.0036(18) 0.005(2) 0.0186(17) N1 0.060(2) 0.0547(19) 0.065(3) 0.0087(17) -0.003(2) 0.0036(18) C17 0.046(2) 0.0483(19) 0.052(3) 0.0044(17) 0.0013(18) 0.0118(17) C19 0.046(2) 0.062(2) 0.072(3) 0.001(2) -0.006(2) 0.0181(19) C18 0.054(2) 0.052(2) 0.071(3) -0.0012(19) -0.003(2) 0.0245(18) C13 0.053(2) 0.0468(19) 0.057(3) 0.0056(17) 0.007(2) 0.0126(18) C23 0.055(2) 0.049(2) 0.066(3) 0.000(2) -0.002(2) 0.0084(19) N3 0.060(2) 0.083(2) 0.072(3) 0.004(2) 0.000(2) 0.0213(18) C20 0.059(2) 0.054(2) 0.078(3) 0.0019(19) -0.011(2) 0.0163(18) C24 0.056(2) 0.081(3) 0.078(4) 0.000(2) 0.006(2) 0.022(2) C22 0.064(2) 0.055(2) 0.091(4) -0.002(2) -0.021(2) 0.0149(19) C21 0.067(2) 0.052(2) 0.076(3) 0.0015(19) -0.009(2) 0.0117(19) C26 0.066(3) 0.106(3) 0.061(3) 0.011(2) -0.004(3) 0.020(2) C25 0.081(3) 0.082(3) 0.060(3) 0.002(2) 0.004(3) 0.027(2) C27 0.061(3) 0.116(3) 0.081(4) 0.007(3) 0.007(3) 0.029(2) C2 0.052(2) 0.063(2) 0.057(3) 0.004(2) 0.004(2) 0.0220(19) O8 0.0560(17) 0.113(2) 0.102(3) 0.0015(18) -0.0038(18) 0.0239(17) N4 0.070(2) 0.068(2) 0.068(3) 0.003(2) -0.010(2) 0.0298(19) O7 0.0555(17) 0.154(3) 0.091(3) -0.020(2) -0.0015(17) 0.0368(19) O6 0.0681(19) 0.122(2) 0.061(2) -0.0052(18) -0.0058(18) 0.0333(17) C5 0.054(2) 0.060(2) 0.054(3) 0.0044(19) 0.002(2) 0.0233(19) O9 0.088(2) 0.127(2) 0.063(2) -0.007(2) -0.010(2) 0.0357(17) C3 0.063(2) 0.087(3) 0.057(3) -0.006(2) 0.007(2) 0.030(2) C6 0.064(3) 0.084(3) 0.059(3) -0.001(2) 0.004(2) 0.027(2) C1 0.070(3) 0.079(3) 0.056(3) -0.004(2) -0.005(3) 0.029(2) C4 0.048(2) 0.089(3) 0.069(3) 0.000(2) 0.003(2) 0.026(2) C7 0.052(2) 0.102(3) 0.065(3) 0.005(3) 0.008(2) 0.026(2) _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 C8 1.309(4) . ? O1 H1 0.863(10) . ? O5 N2 1.330(3) . ? N2 C15 1.344(3) . ? N2 C19 1.336(4) . ? O2 C8 1.218(4) . ? O4 N1 1.225(4) . ? C14 H14 0.9300 . ? C14 C9 1.374(4) . ? C14 C13 1.380(4) . ? C16 H16 0.9300 . ? C16 C15 1.363(4) . ? C16 C17 1.374(4) . ? C11 H11 0.9300 . ? C11 C12 1.367(5) . ? C11 C10 1.376(4) . ? C12 N1 1.476(4) . ? C12 C13 1.377(4) . ? C8 C9 1.487(4) . ? C9 C10 1.388(4) . ? O3 N1 1.216(4) . ? C15 H15 0.9300 . ? C10 H10 0.9300 . ? C17 C18 1.385(4) . ? C17 C20 1.500(4) . ? C19 H19 0.9300 . ? C19 C18 1.373(4) . ? C18 H18 0.9300 . ? C13 H13 0.9300 . ? C23 C24 1.365(5) . ? C23 C22 1.495(4) . ? C23 C26 1.361(5) . ? N3 C25 1.321(5) . ? N3 C27 1.313(5) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C20 C21 1.509(4) . ? C24 H24 0.9300 . ? C24 C25 1.394(5) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C22 C21 1.503(4) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C26 H26 0.9300 . ? C26 C27 1.379(5) . ? C25 H25 0.9300 . ? C27 H27 0.9300 . ? C2 C3 1.381(4) . ? C2 C1 1.485(5) . ? C2 C7 1.368(5) . ? O8 N4 1.219(4) . ? N4 C5 1.463(4) . ? N4 O9 1.218(4) . ? O7 C1 1.207(4) . ? O6 C1 1.300(5) . ? O6 H6 0.853(10) . ? C5 C6 1.369(5) . ? C5 C4 1.358(5) . ? C3 H3 0.9300 . ? C3 C4 1.388(4) . ? C6 H6A 0.9300 . ? C6 C7 1.380(4) . ? C4 H4 0.9300 . ? C7 H7 0.9300 . ? 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 C8 O1 H1 111(2) . . ? O5 N2 C15 118.9(3) . . ? O5 N2 C19 121.8(3) . . ? C19 N2 C15 119.3(3) . . ? C9 C14 H14 119.8 . . ? C9 C14 C13 120.4(3) . . ? C13 C14 H14 119.8 . . ? C15 C16 H16 119.1 . . ? C15 C16 C17 121.7(3) . . ? C17 C16 H16 119.1 . . ? C12 C11 H11 120.6 . . ? C12 C11 C10 118.8(3) . . ? C10 C11 H11 120.6 . . ? C11 C12 N1 118.6(3) . . ? C11 C12 C13 122.2(3) . . ? C13 C12 N1 119.2(4) . . ? O1 C8 C9 114.1(4) . . ? O2 C8 O1 123.4(3) . . ? O2 C8 C9 122.4(4) . . ? C14 C9 C8 121.8(3) . . ? C14 C9 C10 120.0(3) . . ? C10 C9 C8 118.2(4) . . ? N2 C15 C16 120.7(3) . . ? N2 C15 H15 119.7 . . ? C16 C15 H15 119.7 . . ? C11 C10 C9 120.1(3) . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? O4 N1 C12 118.0(4) . . ? O3 N1 O4 123.4(3) . . ? O3 N1 C12 118.5(4) . . ? C16 C17 C18 116.5(3) . . ? C16 C17 C20 123.6(3) . . ? C18 C17 C20 119.9(3) . . ? N2 C19 H19 119.3 . . ? N2 C19 C18 121.4(3) . . ? C18 C19 H19 119.3 . . ? C17 C18 H18 119.8 . . ? C19 C18 C17 120.4(3) . . ? C19 C18 H18 119.8 . . ? C14 C13 H13 120.8 . . ? C12 C13 C14 118.5(4) . . ? C12 C13 H13 120.8 . . ? C24 C23 C22 122.8(4) . . ? C26 C23 C24 116.8(3) . . ? C26 C23 C22 120.4(4) . . ? C27 N3 C25 116.6(4) . . ? C17 C20 H20A 108.3 . . ? C17 C20 H20B 108.3 . . ? C17 C20 C21 115.9(3) . . ? H20A C20 H20B 107.4 . . ? C21 C20 H20A 108.3 . . ? C21 C20 H20B 108.3 . . ? C23 C24 H24 120.1 . . ? C23 C24 C25 119.9(4) . . ? C25 C24 H24 120.1 . . ? C23 C22 H22A 109.0 . . ? C23 C22 H22B 109.0 . . ? C23 C22 C21 113.0(3) . . ? H22A C22 H22B 107.8 . . ? C21 C22 H22A 109.0 . . ? C21 C22 H22B 109.0 . . ? C20 C21 H21A 108.8 . . ? C20 C21 H21B 108.8 . . ? C22 C21 C20 113.9(3) . . ? C22 C21 H21A 108.8 . . ? C22 C21 H21B 108.8 . . ? H21A C21 H21B 107.7 . . ? C23 C26 H26 120.0 . . ? C23 C26 C27 120.0(4) . . ? C27 C26 H26 120.0 . . ? N3 C25 C24 122.9(4) . . ? N3 C25 H25 118.6 . . ? C24 C25 H25 118.6 . . ? N3 C27 C26 123.8(4) . . ? N3 C27 H27 118.1 . . ? C26 C27 H27 118.1 . . ? C3 C2 C1 122.1(4) . . ? C7 C2 C3 118.8(3) . . ? C7 C2 C1 119.1(4) . . ? O8 N4 C5 118.9(4) . . ? O9 N4 O8 122.8(4) . . ? O9 N4 C5 118.3(4) . . ? C1 O6 H6 112(4) . . ? C6 C5 N4 119.2(4) . . ? C4 C5 N4 119.2(4) . . ? C4 C5 C6 121.5(4) . . ? C2 C3 H3 119.9 . . ? C2 C3 C4 120.3(4) . . ? C4 C3 H3 119.9 . . ? C5 C6 H6A 120.7 . . ? C5 C6 C7 118.6(4) . . ? C7 C6 H6A 120.7 . . ? O7 C1 C2 122.3(4) . . ? O7 C1 O6 123.4(4) . . ? O6 C1 C2 114.3(4) . . ? C5 C4 C3 119.3(4) . . ? C5 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? C2 C7 C6 121.4(4) . . ? C2 C7 H7 119.3 . . ? C6 C7 H7 119.3 . . ? 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 O1 C8 C9 C14 9.9(5) . . . . ? O1 C8 C9 C10 -169.4(3) . . . . ? O5 N2 C15 C16 178.0(3) . . . . ? O5 N2 C19 C18 179.7(3) . . . . ? N2 C19 C18 C17 2.1(6) . . . . ? O2 C8 C9 C14 -170.5(3) . . . . ? O2 C8 C9 C10 10.2(5) . . . . ? C14 C9 C10 C11 0.1(5) . . . . ? C16 C17 C18 C19 -0.8(5) . . . . ? C16 C17 C20 C21 20.8(5) . . . . ? C11 C12 N1 O4 -4.0(5) . . . . ? C11 C12 N1 O3 173.9(3) . . . . ? C11 C12 C13 C14 -0.5(5) . . . . ? C12 C11 C10 C9 -0.3(5) . . . . ? C8 C9 C10 C11 179.3(3) . . . . ? C9 C14 C13 C12 0.3(4) . . . . ? C15 N2 C19 C18 -1.1(5) . . . . ? C15 C16 C17 C18 -1.5(5) . . . . ? C15 C16 C17 C20 176.5(3) . . . . ? C10 C11 C12 N1 -179.7(3) . . . . ? C10 C11 C12 C13 0.5(5) . . . . ? N1 C12 C13 C14 179.7(3) . . . . ? C17 C16 C15 N2 2.6(6) . . . . ? C17 C20 C21 C22 178.0(3) . . . . ? C19 N2 C15 C16 -1.2(5) . . . . ? C18 C17 C20 C21 -161.2(3) . . . . ? C13 C14 C9 C8 -179.3(3) . . . . ? C13 C14 C9 C10 -0.1(5) . . . . ? C13 C12 N1 O4 175.8(3) . . . . ? C13 C12 N1 O3 -6.3(5) . . . . ? C23 C24 C25 N3 -0.5(6) . . . . ? C23 C22 C21 C20 -176.2(4) . . . . ? C23 C26 C27 N3 -1.4(6) . . . . ? C20 C17 C18 C19 -178.9(3) . . . . ? C24 C23 C22 C21 95.0(4) . . . . ? C24 C23 C26 C27 2.5(5) . . . . ? C22 C23 C24 C25 179.6(3) . . . . ? C22 C23 C26 C27 -178.6(3) . . . . ? C26 C23 C24 C25 -1.6(5) . . . . ? C26 C23 C22 C21 -83.8(4) . . . . ? C25 N3 C27 C26 -0.7(6) . . . . ? C27 N3 C25 C24 1.6(6) . . . . ? C2 C3 C4 C5 0.4(5) . . . . ? O8 N4 C5 C6 -167.8(3) . . . . ? O8 N4 C5 C4 12.0(5) . . . . ? N4 C5 C6 C7 179.4(3) . . . . ? N4 C5 C4 C3 -180.0(3) . . . . ? C5 C6 C7 C2 0.8(6) . . . . ? O9 N4 C5 C6 12.2(5) . . . . ? O9 N4 C5 C4 -168.0(4) . . . . ? C3 C2 C1 O7 179.6(4) . . . . ? C3 C2 C1 O6 0.8(5) . . . . ? C3 C2 C7 C6 -0.6(6) . . . . ? C6 C5 C4 C3 -0.2(5) . . . . ? C1 C2 C3 C4 179.8(3) . . . . ? C1 C2 C7 C6 179.6(3) . . . . ? C4 C5 C6 C7 -0.3(5) . . . . ? C7 C2 C3 C4 0.0(5) . . . . ? C7 C2 C1 O7 -0.7(6) . . . . ? C7 C2 C1 O6 -179.5(3) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 974283' ####################################################################### # # 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_TBPO-pcba _audit_creation_date 2012-10-10 _audit_creation_method ; Olex2 1.2 (compiled 2012.05.09 svn.r2324, GUI svn.r4230) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C13 H14 N2 O, 2(C8 H5 N O2)' _chemical_formula_sum 'C29 H24 N4 O5' _chemical_formula_weight 508.52 _chemical_melting_point ? 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' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _cell_length_a 15.3106(11) _cell_length_b 11.2938(7) _cell_length_c 14.6971(7) _cell_angle_alpha 90.00 _cell_angle_beta 99.163(6) _cell_angle_gamma 90.00 _cell_volume 2508.9(3) _cell_formula_units_Z 4 _cell_measurement_reflns_used ? _cell_measurement_temperature 298(2) _cell_measurement_theta_max ? _cell_measurement_theta_min ? _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_T_max 0.9796 _exptl_absorpt_correction_T_min 0.9589 _exptl_absorpt_correction_type ? _exptl_absorpt_process_details ? _exptl_crystal_colour ? _exptl_crystal_density_diffrn 1.346 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description ? _exptl_crystal_F_000 1064 _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.22 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0564 _diffrn_reflns_av_unetI/netI 0.0547 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 20450 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 2.70 _diffrn_ambient_temperature 298(2) _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 2265 _reflns_number_total 4428 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ? _computing_data_collection ? _computing_data_reduction ? _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; SHELXS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.187 _refine_diff_density_min -0.145 _refine_diff_density_rms 0.035 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.997 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 347 _refine_ls_number_reflns 4428 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1305 _refine_ls_R_factor_gt 0.0551 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0700P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1218 _refine_ls_wR_factor_ref 0.1584 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 O5 O 0.95806(13) 0.91579(17) 0.78804(13) 0.0760(7) Uani 1 1 d . . . O4 O 0.50075(16) 0.6420(2) 0.86748(15) 0.0978(8) Uani 1 1 d . . . O3 O 0.50886(16) 0.8351(2) 0.89727(16) 0.0836(7) Uani 1 1 d D . . N4 N 0.92555(14) 0.8528(2) 0.71403(15) 0.0578(6) Uani 1 1 d . . . N3 N 0.59126(15) 0.7666(2) 0.05870(16) 0.0627(7) Uani 1 1 d . . . N2 N 0.26540(19) 0.8815(2) 0.41558(19) 0.0914(10) Uani 1 1 d . . . C23 C 0.76567(18) 0.7208(2) 0.39219(17) 0.0594(8) Uani 1 1 d . . . H23A H 0.7191 0.7694 0.4103 0.071 Uiso 1 1 calc R . . H23B H 0.8071 0.7726 0.3682 0.071 Uiso 1 1 calc R . . C27 C 0.59257(18) 0.6521(3) 0.08119(19) 0.0660(9) Uani 1 1 d . . . H27 H 0.5636 0.5988 0.0384 0.079 Uiso 1 1 calc R . . C24 C 0.72616(18) 0.6348(3) 0.31802(18) 0.0646(9) Uani 1 1 d . . . H24A H 0.7735 0.5845 0.3037 0.078 Uiso 1 1 calc R . . H24B H 0.6850 0.5844 0.3438 0.078 Uiso 1 1 calc R . . C28 C 0.67682(19) 0.8028(3) 0.2057(2) 0.0643(8) Uani 1 1 d . . . H28 H 0.7053 0.8579 0.2473 0.077 Uiso 1 1 calc R . . C21 C 0.87889(18) 0.9089(3) 0.64192(19) 0.0631(8) Uani 1 1 d . . . H21 H 0.8715 0.9905 0.6442 0.076 Uiso 1 1 calc R . . C26 C 0.63413(19) 0.6088(3) 0.16348(19) 0.0651(9) Uani 1 1 d . . . H26 H 0.6326 0.5281 0.1757 0.078 Uiso 1 1 calc R . . C12 C 0.36997(19) 0.7112(3) 0.5999(2) 0.0637(8) Uani 1 1 d . . . H12 H 0.3540 0.6508 0.5575 0.076 Uiso 1 1 calc R . . C20 C 0.84187(18) 0.8477(3) 0.56485(18) 0.0602(8) Uani 1 1 d . . . H20 H 0.8086 0.8884 0.5162 0.072 Uiso 1 1 calc R . . C29 C 0.63308(19) 0.8397(3) 0.1211(2) 0.0673(9) Uani 1 1 d . . . H29 H 0.6330 0.9201 0.1073 0.081 Uiso 1 1 calc R . . C22 C 0.81310(19) 0.6546(3) 0.47566(18) 0.0636(8) Uani 1 1 d . . . H22A H 0.7715 0.5993 0.4956 0.076 Uiso 1 1 calc R . . H22B H 0.8600 0.6081 0.4560 0.076 Uiso 1 1 calc R . . C17 C 0.93832(18) 0.7357(3) 0.7099(2) 0.0605(8) Uani 1 1 d . . . H17 H 0.9714 0.6968 0.7596 0.073 Uiso 1 1 calc R . . C25 C 0.67840(17) 0.6848(3) 0.22859(18) 0.0540(8) Uani 1 1 d . . . C9 C 0.4854(2) 0.7438(3) 0.8441(2) 0.0639(9) Uani 1 1 d . . . C18 C 0.90291(18) 0.6731(3) 0.63320(19) 0.0604(8) Uani 1 1 d . . . H18 H 0.9128 0.5919 0.6317 0.073 Uiso 1 1 calc R . . C19 C 0.85287(17) 0.7266(3) 0.55790(18) 0.0510(7) Uani 1 1 d . . . C13 C 0.35013(17) 0.8278(3) 0.57652(19) 0.0563(8) Uani 1 1 d . . . C11 C 0.41381(18) 0.6860(3) 0.68725(19) 0.0613(8) Uani 1 1 d . . . H11 H 0.4273 0.6079 0.7037 0.074 Uiso 1 1 calc R . . C10 C 0.43796(17) 0.7752(3) 0.7506(2) 0.0556(8) Uani 1 1 d . . . C15 C 0.41833(18) 0.8908(3) 0.7254(2) 0.0655(9) Uani 1 1 d . . . H15 H 0.4349 0.9515 0.7673 0.079 Uiso 1 1 calc R . . C16 C 0.3032(2) 0.8565(3) 0.4864(2) 0.0682(9) Uani 1 1 d . . . C14 C 0.37455(18) 0.9173(3) 0.6388(2) 0.0665(9) Uani 1 1 d . . . H14 H 0.3615 0.9956 0.6223 0.080 Uiso 1 1 calc R . . O2 O 0.98677(16) 0.16208(19) 0.58697(14) 0.0919(8) Uani 1 1 d . . . O1 O 0.95756(13) 0.35165(18) 0.55760(13) 0.0752(6) Uani 1 1 d D . . H1 H 0.9883 0.3554 0.6257 0.090 Uiso 1 1 d RD . . N1 N 0.74525(19) 0.0915(2) 0.10493(19) 0.0869(9) Uani 1 1 d . . . C5 C 0.82364(17) 0.1545(3) 0.26630(18) 0.0544(7) Uani 1 1 d . . . C6 C 0.82529(19) 0.2709(3) 0.2955(2) 0.0630(8) Uani 1 1 d . . . H6 H 0.7987 0.3297 0.2562 0.076 Uiso 1 1 calc R . . C2 C 0.90650(17) 0.2128(3) 0.44153(18) 0.0525(7) Uani 1 1 d . . . C3 C 0.90463(18) 0.0968(3) 0.41126(19) 0.0605(8) Uani 1 1 d . . . H3 H 0.9315 0.0379 0.4502 0.073 Uiso 1 1 calc R . . C4 C 0.86363(18) 0.0679(3) 0.32455(19) 0.0621(8) Uani 1 1 d . . . H4 H 0.8627 -0.0105 0.3049 0.075 Uiso 1 1 calc R . . C1 C 0.95356(19) 0.2397(3) 0.5358(2) 0.0608(8) Uani 1 1 d . . . C8 C 0.7798(2) 0.1214(3) 0.1761(2) 0.0648(9) Uani 1 1 d . . . C7 C 0.86642(19) 0.2997(3) 0.3829(2) 0.0643(8) Uani 1 1 d . . . H7 H 0.8673 0.3780 0.4026 0.077 Uiso 1 1 calc R . . H3A H 0.534(2) 0.817(3) 0.9527(11) 0.118(14) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O5 0.1061(17) 0.0638(14) 0.0485(12) -0.0046(10) -0.0164(12) 0.0001(11) O4 0.144(2) 0.0619(16) 0.0706(16) 0.0025(13) -0.0333(15) 0.0062(14) O3 0.1063(18) 0.0726(16) 0.0600(15) -0.0072(13) -0.0227(14) -0.0013(13) N4 0.0705(16) 0.0588(17) 0.0407(14) 0.0035(13) -0.0022(12) -0.0008(13) N3 0.0638(16) 0.0680(19) 0.0529(16) -0.0077(14) -0.0004(13) -0.0044(13) N2 0.117(2) 0.077(2) 0.0679(19) 0.0085(16) -0.0224(18) 0.0023(16) C23 0.070(2) 0.064(2) 0.0419(17) -0.0021(15) 0.0002(15) -0.0066(15) C27 0.074(2) 0.071(2) 0.0489(19) -0.0179(17) -0.0011(16) -0.0150(17) C24 0.077(2) 0.062(2) 0.0520(18) -0.0018(15) 0.0006(16) -0.0048(15) C28 0.078(2) 0.058(2) 0.0504(18) -0.0051(15) -0.0092(16) -0.0089(16) C21 0.084(2) 0.0514(19) 0.0499(18) 0.0038(15) -0.0031(16) 0.0058(15) C26 0.085(2) 0.059(2) 0.0503(18) -0.0069(15) 0.0063(17) -0.0118(16) C12 0.078(2) 0.055(2) 0.0531(19) -0.0024(15) -0.0043(16) -0.0036(16) C20 0.073(2) 0.059(2) 0.0433(17) 0.0073(15) -0.0055(15) 0.0033(15) C29 0.081(2) 0.057(2) 0.059(2) -0.0063(17) -0.0048(17) -0.0070(16) C22 0.077(2) 0.061(2) 0.0496(18) 0.0024(15) -0.0012(16) -0.0030(15) C17 0.069(2) 0.060(2) 0.0498(19) 0.0099(16) -0.0012(16) 0.0077(15) C25 0.0554(18) 0.063(2) 0.0421(16) -0.0047(15) 0.0019(14) -0.0038(14) C9 0.070(2) 0.066(2) 0.052(2) -0.0046(17) -0.0021(17) -0.0035(16) C18 0.076(2) 0.0501(19) 0.0525(18) 0.0038(15) 0.0014(16) 0.0045(15) C19 0.0558(17) 0.0561(19) 0.0395(16) 0.0042(14) 0.0029(14) 0.0007(14) C13 0.0557(18) 0.059(2) 0.0498(17) 0.0023(15) -0.0039(15) -0.0005(15) C11 0.078(2) 0.0497(19) 0.0511(18) 0.0001(15) -0.0056(16) 0.0013(15) C10 0.0547(17) 0.058(2) 0.0519(18) 0.0023(15) 0.0005(15) 0.0006(14) C15 0.070(2) 0.057(2) 0.064(2) -0.0094(16) -0.0069(17) -0.0032(15) C16 0.081(2) 0.056(2) 0.062(2) 0.0017(17) -0.0024(19) 0.0009(16) C14 0.074(2) 0.054(2) 0.066(2) 0.0050(17) -0.0061(17) 0.0044(15) O2 0.142(2) 0.0640(15) 0.0563(13) 0.0056(12) -0.0261(14) 0.0074(14) O1 0.0999(16) 0.0613(15) 0.0551(13) -0.0080(11) -0.0163(11) 0.0110(12) N1 0.118(2) 0.072(2) 0.0618(18) -0.0054(15) -0.0153(17) -0.0078(16) C5 0.0575(18) 0.059(2) 0.0443(17) -0.0008(15) -0.0002(14) -0.0014(15) C6 0.075(2) 0.058(2) 0.0508(19) 0.0028(15) -0.0064(16) 0.0058(16) C2 0.0521(17) 0.058(2) 0.0449(17) 0.0018(15) 0.0014(14) -0.0009(14) C3 0.073(2) 0.051(2) 0.0533(19) 0.0059(15) -0.0028(16) 0.0023(15) C4 0.076(2) 0.0513(19) 0.0556(19) -0.0027(15) 0.0007(16) -0.0036(15) C1 0.067(2) 0.062(2) 0.0486(19) 0.0028(16) -0.0056(16) 0.0027(16) C8 0.077(2) 0.054(2) 0.059(2) -0.0028(16) -0.0017(18) -0.0039(15) C7 0.080(2) 0.0513(19) 0.056(2) -0.0047(16) -0.0061(17) 0.0050(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 O5 N4 1.328(3) . ? O4 C9 1.212(3) . ? O3 C9 1.309(4) . ? O3 H3A 0.868(10) . ? N4 C21 1.339(3) . ? N4 C17 1.339(3) . ? N3 C27 1.335(4) . ? N3 C29 1.321(3) . ? N2 C16 1.143(3) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C23 C24 1.512(3) . ? C23 C22 1.519(3) . ? C27 H27 0.9300 . ? C27 C26 1.364(4) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C24 C25 1.508(4) . ? C28 H28 0.9300 . ? C28 C29 1.380(4) . ? C28 C25 1.374(4) . ? C21 H21 0.9300 . ? C21 C20 1.370(4) . ? C26 H26 0.9300 . ? C26 C25 1.381(4) . ? C12 H12 0.9300 . ? C12 C13 1.383(4) . ? C12 C11 1.380(4) . ? C20 H20 0.9300 . ? C20 C19 1.383(4) . ? C29 H29 0.9300 . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C22 C19 1.503(4) . ? C17 H17 0.9300 . ? C17 C18 1.368(4) . ? C9 C10 1.491(4) . ? C18 H18 0.9300 . ? C18 C19 1.381(4) . ? C13 C16 1.440(4) . ? C13 C14 1.374(4) . ? C11 H11 0.9300 . ? C11 C10 1.381(4) . ? C10 C15 1.378(4) . ? C15 H15 0.9300 . ? C15 C14 1.374(4) . ? C14 H14 0.9300 . ? O2 C1 1.213(3) . ? O1 H1 1.0365 . ? O1 C1 1.303(3) . ? N1 C8 1.145(3) . ? C5 C6 1.382(4) . ? C5 C4 1.378(4) . ? C5 C8 1.437(4) . ? C6 H6 0.9300 . ? C6 C7 1.375(4) . ? C2 C3 1.382(4) . ? C2 C1 1.488(4) . ? C2 C7 1.384(4) . ? C3 H3 0.9300 . ? C3 C4 1.367(4) . ? C4 H4 0.9300 . ? C7 H7 0.9300 . ? 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 O3 H3A 114(2) . . ? O5 N4 C21 118.5(2) . . ? O5 N4 C17 121.8(2) . . ? C21 N4 C17 119.7(2) . . ? C29 N3 C27 116.6(3) . . ? H23A C23 H23B 108.1 . . ? C24 C23 H23A 109.5 . . ? C24 C23 H23B 109.5 . . ? C24 C23 C22 110.5(2) . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? N3 C27 H27 118.2 . . ? N3 C27 C26 123.6(3) . . ? C26 C27 H27 118.2 . . ? C23 C24 H24A 107.8 . . ? C23 C24 H24B 107.8 . . ? H24A C24 H24B 107.1 . . ? C25 C24 C23 118.1(2) . . ? C25 C24 H24A 107.8 . . ? C25 C24 H24B 107.8 . . ? C29 C28 H28 120.0 . . ? C25 C28 H28 120.0 . . ? C25 C28 C29 120.0(3) . . ? N4 C21 H21 119.5 . . ? N4 C21 C20 120.9(3) . . ? C20 C21 H21 119.5 . . ? C27 C26 H26 120.0 . . ? C27 C26 C25 120.0(3) . . ? C25 C26 H26 120.0 . . ? C13 C12 H12 120.6 . . ? C11 C12 H12 120.6 . . ? C11 C12 C13 118.9(3) . . ? C21 C20 H20 119.3 . . ? C21 C20 C19 121.4(3) . . ? C19 C20 H20 119.3 . . ? N3 C29 C28 123.3(3) . . ? N3 C29 H29 118.4 . . ? C28 C29 H29 118.4 . . ? C23 C22 H22A 107.9 . . ? C23 C22 H22B 107.9 . . ? H22A C22 H22B 107.2 . . ? C19 C22 C23 117.6(2) . . ? C19 C22 H22A 107.9 . . ? C19 C22 H22B 107.9 . . ? N4 C17 H17 119.8 . . ? N4 C17 C18 120.4(3) . . ? C18 C17 H17 119.8 . . ? C28 C25 C24 124.3(2) . . ? C28 C25 C26 116.5(3) . . ? C26 C25 C24 119.2(3) . . ? O4 C9 O3 123.7(3) . . ? O4 C9 C10 122.1(3) . . ? O3 C9 C10 114.2(3) . . ? C17 C18 H18 119.0 . . ? C17 C18 C19 122.0(3) . . ? C19 C18 H18 119.0 . . ? C20 C19 C22 123.8(2) . . ? C18 C19 C20 115.6(2) . . ? C18 C19 C22 120.6(3) . . ? C12 C13 C16 120.1(3) . . ? C14 C13 C12 120.6(3) . . ? C14 C13 C16 119.4(3) . . ? C12 C11 H11 119.5 . . ? C12 C11 C10 121.0(3) . . ? C10 C11 H11 119.5 . . ? C11 C10 C9 119.1(3) . . ? C15 C10 C9 121.8(3) . . ? C15 C10 C11 119.1(3) . . ? C10 C15 H15 119.7 . . ? C14 C15 C10 120.6(3) . . ? C14 C15 H15 119.7 . . ? N2 C16 C13 178.5(4) . . ? C13 C14 H14 120.1 . . ? C15 C14 C13 119.9(3) . . ? C15 C14 H14 120.1 . . ? C1 O1 H1 105.8 . . ? C6 C5 C8 121.2(3) . . ? C4 C5 C6 119.9(3) . . ? C4 C5 C8 119.0(3) . . ? C5 C6 H6 120.1 . . ? C7 C6 C5 119.8(3) . . ? C7 C6 H6 120.1 . . ? C3 C2 C1 118.4(3) . . ? C3 C2 C7 119.2(3) . . ? C7 C2 C1 122.4(3) . . ? C2 C3 H3 119.7 . . ? C4 C3 C2 120.6(3) . . ? C4 C3 H3 119.7 . . ? C5 C4 H4 119.9 . . ? C3 C4 C5 120.1(3) . . ? C3 C4 H4 119.9 . . ? O2 C1 O1 123.4(3) . . ? O2 C1 C2 121.5(3) . . ? O1 C1 C2 115.1(3) . . ? N1 C8 C5 178.0(3) . . ? C6 C7 C2 120.4(3) . . ? C6 C7 H7 119.8 . . ? C2 C7 H7 119.8 . . ? _database_code_depnum_ccdc_archive 'CCDC 974284' ####################################################################### # # 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_TBPO-phba _audit_creation_date 2012-10-10 _audit_creation_method ; Olex2 1.2 (compiled 2012.05.09 svn.r2324, GUI svn.r4230) ; _chemical_name_common 'TBPO.4-hydroxybenzoic acid' _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C7 H6 O3, C13 H14 N2 O' _chemical_formula_sum 'C20 H20 N2 O4' _chemical_formula_weight 352.38 _chemical_melting_point ? 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' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 6.2766(9) _cell_length_b 7.8957(13) _cell_length_c 17.992(3) _cell_angle_alpha 100.669(13) _cell_angle_beta 93.653(12) _cell_angle_gamma 95.958(13) _cell_volume 868.3(2) _cell_formula_units_Z 2 _cell_measurement_reflns_used 2100 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 29.3971 _cell_measurement_theta_min 2.6381 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.94554 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour ? _exptl_crystal_density_diffrn 1.348 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description ? _exptl_crystal_F_000 372 _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.31 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0559 _diffrn_reflns_av_unetI/netI 0.0922 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 7466 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 2.64 _diffrn_ambient_temperature 298(2) _diffrn_detector_area_resol_mean 15.9821 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -8.00 86.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - 18.9803 77.0000 0.0000 94 #__ type_ start__ end____ width___ exp.time_ 2 omega -48.00 -19.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - 18.9803 -77.0000 120.0000 29 #__ type_ start__ end____ width___ exp.time_ 3 omega -7.00 88.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - 18.9803 77.0000 150.0000 95 #__ type_ start__ end____ width___ exp.time_ 4 omega 16.00 42.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - 18.9803 52.0000 109.0000 26 #__ type_ start__ end____ width___ exp.time_ 5 omega -45.00 48.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - 18.9803 -77.0000 -120.0000 93 #__ type_ start__ end____ width___ exp.time_ 6 omega -94.00 -32.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - -17.3397 179.0000 30.0000 62 #__ type_ start__ end____ width___ exp.time_ 7 omega -94.00 -32.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - -17.3397 179.0000 -90.0000 62 #__ type_ start__ end____ width___ exp.time_ 8 omega -11.00 14.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - 18.9803 77.0000 -120.0000 25 ; _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0772008000 _diffrn_orient_matrix_UB_12 0.0417564000 _diffrn_orient_matrix_UB_13 -0.0198242000 _diffrn_orient_matrix_UB_21 0.0362111000 _diffrn_orient_matrix_UB_22 -0.0810767000 _diffrn_orient_matrix_UB_23 -0.0140767000 _diffrn_orient_matrix_UB_31 -0.0757112000 _diffrn_orient_matrix_UB_32 -0.0125411000 _diffrn_orient_matrix_UB_33 -0.0320925000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 1585 _reflns_number_total 3067 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; SHELXS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.282 _refine_diff_density_min -0.193 _refine_diff_density_rms 0.064 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.995 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 243 _refine_ls_number_reflns 3067 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1378 _refine_ls_R_factor_gt 0.0728 _refine_ls_restrained_S_all 0.995 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0875P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1627 _refine_ls_wR_factor_ref 0.2071 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 1.1364(4) 0.4717(4) 0.38630(15) 0.0643(8) Uani 1 1 d D . . O2 O 0.8387(4) 0.6017(3) 0.39969(15) 0.0734(9) Uani 1 1 d . . . O3 O 0.5941(4) 0.0867(3) 0.08479(15) 0.0603(8) Uani 1 1 d D . . C5 C 0.6678(5) 0.1760(4) 0.1558(2) 0.0455(9) Uani 1 1 d . . . C2 C 0.8424(5) 0.3709(4) 0.29529(18) 0.0411(9) Uani 1 1 d . . . C3 C 0.6326(5) 0.3806(4) 0.26851(19) 0.0454(9) Uani 1 1 d . . . H3A H 0.5492 0.4526 0.2980 0.054 Uiso 1 1 calc R . . N1 N 0.2972(5) -0.2809(4) 0.50205(17) 0.0534(9) Uani 1 1 d . . . C7 C 0.9589(6) 0.2539(4) 0.25356(19) 0.0469(9) Uani 1 1 d . . . H7 H 1.0964 0.2404 0.2722 0.056 Uiso 1 1 calc R . . O4 O 1.3291(4) 0.3044(4) 1.04418(16) 0.0823(10) Uani 1 1 d . . . C16 C 0.8935(5) 0.3044(4) 0.8651(2) 0.0452(9) Uani 1 1 d . . . N2 N 1.1900(5) 0.3008(4) 0.98553(17) 0.0546(9) Uani 1 1 d . . . C4 C 0.5451(5) 0.2860(4) 0.19907(19) 0.0461(9) Uani 1 1 d . . . H4 H 0.4052 0.2960 0.1815 0.055 Uiso 1 1 calc R . . C1 C 0.9354(6) 0.4911(5) 0.3657(2) 0.0489(10) Uani 1 1 d . . . C10 C 0.4443(6) -0.0024(4) 0.61966(19) 0.0474(9) Uani 1 1 d . . . C9 C 0.5782(6) -0.1204(5) 0.5898(2) 0.0577(11) Uani 1 1 d . . . H9 H 0.7214 -0.1086 0.6087 0.069 Uiso 1 1 calc R . . C6 C 0.8728(6) 0.1565(5) 0.1843(2) 0.0523(10) Uani 1 1 d . . . H6 H 0.9524 0.0777 0.1566 0.063 Uiso 1 1 calc R . . C20 C 1.2472(6) 0.3773(5) 0.9282(2) 0.0625(12) Uani 1 1 d . . . H20 H 1.3871 0.4302 0.9292 0.075 Uiso 1 1 calc R . . C19 C 1.1030(6) 0.3788(5) 0.8683(2) 0.0582(11) Uani 1 1 d . . . H19 H 1.1473 0.4313 0.8288 0.070 Uiso 1 1 calc R . . C12 C 0.1670(6) -0.1702(5) 0.5317(2) 0.0565(11) Uani 1 1 d . . . H12 H 0.0231 -0.1882 0.5131 0.068 Uiso 1 1 calc R . . C14 C 0.6885(6) 0.1419(5) 0.7408(2) 0.0531(10) Uani 1 1 d . . . H14A H 0.8197 0.1160 0.7176 0.064 Uiso 1 1 calc R . . H14B H 0.6419 0.0472 0.7657 0.064 Uiso 1 1 calc R . . C8 C 0.4988(6) -0.2554(5) 0.5319(2) 0.0573(11) Uani 1 1 d . . . H8 H 0.5919 -0.3336 0.5126 0.069 Uiso 1 1 calc R . . C15 C 0.7341(6) 0.3088(5) 0.7994(2) 0.0615(11) Uani 1 1 d . . . H15A H 0.7872 0.4012 0.7742 0.074 Uiso 1 1 calc R . . H15B H 0.5997 0.3378 0.8194 0.074 Uiso 1 1 calc R . . C17 C 0.8388(6) 0.2267(5) 0.9244(2) 0.0571(11) Uani 1 1 d . . . H17 H 0.6996 0.1731 0.9242 0.069 Uiso 1 1 calc R . . C18 C 0.9868(6) 0.2268(5) 0.9844(2) 0.0612(11) Uani 1 1 d . . . H18 H 0.9456 0.1752 1.0245 0.073 Uiso 1 1 calc R . . C11 C 0.2342(6) -0.0305(5) 0.5884(2) 0.0593(11) Uani 1 1 d . . . H11 H 0.1376 0.0461 0.6061 0.071 Uiso 1 1 calc R . . C13 C 0.5179(6) 0.1549(5) 0.6802(2) 0.0656(12) Uani 1 1 d . . . H13A H 0.3927 0.1901 0.7052 0.079 Uiso 1 1 calc R . . H13B H 0.5702 0.2479 0.6551 0.079 Uiso 1 1 calc R . . H1 H 1.186(6) 0.549(4) 0.4252(16) 0.102(17) Uiso 1 1 d D . . H3 H 0.490(4) 0.133(4) 0.067(2) 0.070(15) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0545(17) 0.0686(19) 0.0591(18) -0.0142(15) -0.0158(14) 0.0175(14) O2 0.0688(19) 0.0736(19) 0.0654(19) -0.0216(15) -0.0130(15) 0.0250(16) O3 0.0617(19) 0.0645(18) 0.0462(16) -0.0058(14) -0.0077(14) 0.0042(15) C5 0.047(2) 0.043(2) 0.043(2) 0.0062(17) 0.0011(18) -0.0042(16) C2 0.044(2) 0.0379(19) 0.039(2) 0.0055(16) -0.0044(16) 0.0051(16) C3 0.045(2) 0.047(2) 0.046(2) 0.0127(17) 0.0010(17) 0.0102(16) N1 0.057(2) 0.0496(19) 0.0485(19) 0.0006(15) -0.0054(16) 0.0062(16) C7 0.049(2) 0.047(2) 0.043(2) 0.0030(17) -0.0032(17) 0.0141(17) O4 0.087(2) 0.092(2) 0.0611(19) 0.0034(16) -0.0340(17) 0.0214(17) C16 0.045(2) 0.040(2) 0.045(2) -0.0017(17) -0.0038(18) 0.0032(16) N2 0.056(2) 0.061(2) 0.0417(19) -0.0010(16) -0.0102(16) 0.0096(16) C4 0.0363(19) 0.055(2) 0.044(2) 0.0078(17) -0.0037(17) 0.0028(17) C1 0.057(2) 0.045(2) 0.044(2) 0.0071(18) -0.0074(19) 0.0123(18) C10 0.056(2) 0.042(2) 0.041(2) 0.0051(16) -0.0046(18) 0.0010(17) C9 0.046(2) 0.065(3) 0.056(2) 0.002(2) -0.0097(19) 0.0047(19) C6 0.052(2) 0.051(2) 0.052(2) 0.0026(18) 0.0030(19) 0.0153(18) C20 0.049(2) 0.078(3) 0.054(3) 0.012(2) -0.006(2) -0.011(2) C19 0.059(2) 0.068(3) 0.044(2) 0.012(2) -0.0003(19) -0.009(2) C12 0.049(2) 0.063(3) 0.052(2) 0.000(2) -0.0061(19) 0.0059(19) C14 0.056(2) 0.048(2) 0.051(2) 0.0047(18) -0.0058(18) 0.0016(18) C8 0.053(2) 0.061(2) 0.052(2) -0.0032(19) -0.005(2) 0.0114(19) C15 0.061(2) 0.056(2) 0.060(3) -0.001(2) -0.019(2) 0.009(2) C17 0.046(2) 0.059(2) 0.061(3) 0.008(2) 0.003(2) -0.0088(18) C18 0.070(3) 0.069(3) 0.043(2) 0.013(2) 0.004(2) -0.003(2) C11 0.056(2) 0.058(2) 0.057(2) -0.005(2) -0.010(2) 0.0119(19) C13 0.069(3) 0.058(3) 0.059(3) -0.006(2) -0.022(2) 0.007(2) _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 C1 1.325(4) . ? O1 H1 0.856(10) . ? O2 C1 1.210(4) . ? O3 C5 1.366(4) . ? O3 H3 0.854(10) . ? C5 C4 1.385(5) . ? C5 C6 1.389(4) . ? C2 C3 1.388(4) . ? C2 C7 1.380(4) . ? C2 C1 1.480(4) . ? C3 H3A 0.9300 . ? C3 C4 1.379(4) . ? N1 C12 1.322(4) . ? N1 C8 1.323(4) . ? C7 H7 0.9300 . ? C7 C6 1.382(4) . ? O4 N2 1.320(3) . ? C16 C19 1.377(5) . ? C16 C15 1.507(4) . ? C16 C17 1.371(5) . ? N2 C20 1.338(5) . ? N2 C18 1.344(5) . ? C4 H4 0.9300 . ? C10 C9 1.378(5) . ? C10 C11 1.379(4) . ? C10 C13 1.502(5) . ? C9 H9 0.9300 . ? C9 C8 1.371(5) . ? C6 H6 0.9300 . ? C20 H20 0.9300 . ? C20 C19 1.365(5) . ? C19 H19 0.9300 . ? C12 H12 0.9300 . ? C12 C11 1.367(5) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C14 C15 1.517(5) . ? C14 C13 1.505(4) . ? C8 H8 0.9300 . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C17 H17 0.9300 . ? C17 C18 1.378(5) . ? C18 H18 0.9300 . ? C11 H11 0.9300 . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 H1 111(3) . . ? C5 O3 H3 110(3) . . ? O3 C5 C4 121.8(3) . . ? O3 C5 C6 118.5(3) . . ? C4 C5 C6 119.7(3) . . ? C3 C2 C1 118.8(3) . . ? C7 C2 C3 118.6(3) . . ? C7 C2 C1 122.6(3) . . ? C2 C3 H3A 119.3 . . ? C4 C3 C2 121.5(3) . . ? C4 C3 H3A 119.3 . . ? C12 N1 C8 116.9(3) . . ? C2 C7 H7 119.7 . . ? C2 C7 C6 120.6(3) . . ? C6 C7 H7 119.7 . . ? C19 C16 C15 121.2(4) . . ? C17 C16 C19 116.6(3) . . ? C17 C16 C15 122.2(3) . . ? O4 N2 C20 120.3(3) . . ? O4 N2 C18 120.3(4) . . ? C20 N2 C18 119.3(3) . . ? C5 C4 H4 120.4 . . ? C3 C4 C5 119.3(3) . . ? C3 C4 H4 120.4 . . ? O1 C1 C2 114.1(3) . . ? O2 C1 O1 123.0(3) . . ? O2 C1 C2 122.8(3) . . ? C9 C10 C11 116.3(3) . . ? C9 C10 C13 123.7(3) . . ? C11 C10 C13 119.9(3) . . ? C10 C9 H9 120.2 . . ? C8 C9 C10 119.5(3) . . ? C8 C9 H9 120.2 . . ? C5 C6 H6 119.9 . . ? C7 C6 C5 120.1(3) . . ? C7 C6 H6 119.9 . . ? N2 C20 H20 119.6 . . ? N2 C20 C19 120.9(4) . . ? C19 C20 H20 119.6 . . ? C16 C19 H19 119.3 . . ? C20 C19 C16 121.5(4) . . ? C20 C19 H19 119.3 . . ? N1 C12 H12 118.5 . . ? N1 C12 C11 123.0(3) . . ? C11 C12 H12 118.5 . . ? H14A C14 H14B 108.0 . . ? C15 C14 H14A 109.3 . . ? C15 C14 H14B 109.3 . . ? C13 C14 H14A 109.3 . . ? C13 C14 H14B 109.3 . . ? C13 C14 C15 111.6(3) . . ? N1 C8 C9 123.8(4) . . ? N1 C8 H8 118.1 . . ? C9 C8 H8 118.1 . . ? C16 C15 C14 115.4(3) . . ? C16 C15 H15A 108.4 . . ? C16 C15 H15B 108.4 . . ? C14 C15 H15A 108.4 . . ? C14 C15 H15B 108.4 . . ? H15A C15 H15B 107.5 . . ? C16 C17 H17 119.5 . . ? C16 C17 C18 121.0(3) . . ? C18 C17 H17 119.5 . . ? N2 C18 C17 120.7(4) . . ? N2 C18 H18 119.6 . . ? C17 C18 H18 119.6 . . ? C10 C11 H11 119.8 . . ? C12 C11 C10 120.5(4) . . ? C12 C11 H11 119.8 . . ? C10 C13 C14 118.7(3) . . ? C10 C13 H13A 107.6 . . ? C10 C13 H13B 107.6 . . ? C14 C13 H13A 107.6 . . ? C14 C13 H13B 107.6 . . ? H13A C13 H13B 107.1 . . ? _database_code_depnum_ccdc_archive 'CCDC 974285' ####################################################################### # # 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_TBPO-acca _audit_creation_date 2012-10-10 _audit_creation_method ; Olex2 1.2 (compiled 2012.05.09 svn.r2324, GUI svn.r4230) ; _chemical_name_common 'BPO.alpha-cyanocoumaric acid' _chemical_name_systematic ; IUPAC name?????? ; _chemical_formula_moiety 'C10 H6 N O3, C10 H7 N O3, C13 H15 N2 O' _chemical_formula_sum 'C33 H28 N4 O7' _chemical_formula_weight 592.59 _chemical_melting_point ? 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' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 7.3004(9) _cell_length_b 10.1353(13) _cell_length_c 20.884(2) _cell_angle_alpha 99.943(9) _cell_angle_beta 90.989(9) _cell_angle_gamma 108.782(12) _cell_volume 1436.6(3) _cell_formula_units_Z 2 _cell_measurement_reflns_used 3232 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 29.1535 _cell_measurement_theta_min 2.9503 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.65286 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour yellowish _exptl_crystal_density_diffrn 1.370 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 620 _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.08 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0693 _diffrn_reflns_av_unetI/netI 0.1018 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_number 12734 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 2.96 _diffrn_ambient_temperature 298(2) _diffrn_detector_area_resol_mean 15.9821 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -11.00 89.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 19.1366 77.0000 -120.0000 100 #__ type_ start__ end____ width___ exp.time_ 2 omega -10.00 37.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 19.1366 77.0000 0.0000 47 #__ type_ start__ end____ width___ exp.time_ 3 omega -44.00 46.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 19.1366 -77.0000 120.0000 90 #__ type_ start__ end____ width___ exp.time_ 4 omega -2.00 85.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 19.1366 77.0000 30.0000 87 #__ type_ start__ end____ width___ exp.time_ 5 omega -47.00 -20.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 19.1366 -37.0000 -90.0000 27 #__ type_ start__ end____ width___ exp.time_ 6 omega -4.00 34.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 19.1366 -37.0000 -90.0000 38 #__ type_ start__ end____ width___ exp.time_ 7 omega -43.00 29.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 19.1366 -77.0000 -180.0000 72 #__ type_ start__ end____ width___ exp.time_ 8 omega -51.00 1.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 19.1366 -77.0000 -90.0000 52 ; _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0752287000 _diffrn_orient_matrix_UB_12 0.0660818000 _diffrn_orient_matrix_UB_13 0.0095190000 _diffrn_orient_matrix_UB_21 -0.0012934000 _diffrn_orient_matrix_UB_22 0.0114414000 _diffrn_orient_matrix_UB_23 -0.0325426000 _diffrn_orient_matrix_UB_31 -0.0702511000 _diffrn_orient_matrix_UB_32 0.0341641000 _diffrn_orient_matrix_UB_33 0.0068333000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 2577 _reflns_number_total 5039 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; SHELXS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.448 _refine_diff_density_min -0.330 _refine_diff_density_rms 0.101 _refine_ls_extinction_coef 0.010(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 414 _refine_ls_number_reflns 5039 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.1791 _refine_ls_R_factor_gt 0.1181 _refine_ls_restrained_S_all 1.061 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.3032 _refine_ls_wR_factor_ref 0.3593 _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. DFIX 0.91 N3 H3 DFIX 0.85 O1 H1 O3 H3b O6 H6a ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 O5 O 0.1409(6) 0.4001(4) 0.06124(17) 0.0613(11) Uani 1 1 d . . . O4 O 0.2518(7) 0.6359(4) 0.08822(19) 0.0705(12) Uani 1 1 d . . . O6 O 0.0449(7) 0.7208(5) 0.48260(19) 0.0727(13) Uani 1 1 d D . . C20 C 0.0518(8) 0.3618(6) 0.1823(2) 0.0497(13) Uani 1 1 d . . . C12 C 0.1310(7) 0.5033(5) 0.1698(2) 0.0443(12) Uani 1 1 d . . . C13 C 0.1701(8) 0.6183(6) 0.2167(2) 0.0497(13) Uani 1 1 d . . . H13 H 0.2315 0.7033 0.2031 0.060 Uiso 1 1 calc R . . C19 C -0.0069(8) 0.5360(6) 0.3139(3) 0.0531(14) Uani 1 1 d . . . H19 H -0.0807 0.4501 0.2880 0.064 Uiso 1 1 calc R . . C14 C 0.1337(8) 0.6342(6) 0.2856(2) 0.0507(14) Uani 1 1 d . . . C16 C 0.2162(9) 0.7855(6) 0.3918(3) 0.0645(16) Uani 1 1 d . . . H16 H 0.2936 0.8696 0.4180 0.077 Uiso 1 1 calc R . . C18 C -0.0394(8) 0.5625(6) 0.3787(2) 0.0537(14) Uani 1 1 d . . . H18 H -0.1371 0.4967 0.3958 0.064 Uiso 1 1 calc R . . C11 C 0.1804(8) 0.5161(6) 0.1007(2) 0.0470(13) Uani 1 1 d . . . N2 N -0.0039(8) 0.2494(6) 0.1918(3) 0.0730(15) Uani 1 1 d . . . C17 C 0.0740(8) 0.6882(6) 0.4189(2) 0.0537(14) Uani 1 1 d . . . C15 C 0.2438(8) 0.7589(6) 0.3267(3) 0.0588(15) Uani 1 1 d . . . H15 H 0.3389 0.8263 0.3095 0.071 Uiso 1 1 calc R . . O1 O 0.7753(6) 0.5959(4) 0.05370(18) 0.0627(11) Uani 1 1 d D . . O2 O 0.9189(6) 0.8315(4) 0.07028(19) 0.0661(12) Uani 1 1 d . . . C3 C 0.8447(7) 0.8461(6) 0.2015(2) 0.0462(13) Uani 1 1 d . . . H3A H 0.9108 0.9243 0.1835 0.055 Uiso 1 1 calc R . . O3 O 0.7845(7) 0.9975(5) 0.4699(2) 0.0782(14) Uani 1 1 d D . . C2 C 0.7857(7) 0.7236(5) 0.1588(2) 0.0448(13) Uani 1 1 d . . . C6 C 0.8923(8) 1.0638(6) 0.3678(3) 0.0543(14) Uani 1 1 d . . . H6 H 0.9454 1.1590 0.3871 0.065 Uiso 1 1 calc R . . C4 C 0.8241(7) 0.8796(5) 0.2716(2) 0.0437(12) Uani 1 1 d . . . C10 C 0.6818(8) 0.5888(6) 0.1747(3) 0.0545(14) Uani 1 1 d . . . C1 C 0.8333(7) 0.7221(6) 0.0894(3) 0.0491(13) Uani 1 1 d . . . C9 C 0.7398(8) 0.7811(6) 0.3102(3) 0.0581(15) Uani 1 1 d . . . H9 H 0.6901 0.6854 0.2912 0.070 Uiso 1 1 calc R . . C7 C 0.8021(8) 0.9632(6) 0.4051(2) 0.0505(14) Uani 1 1 d . . . C5 C 0.9021(8) 1.0214(6) 0.3024(2) 0.0513(14) Uani 1 1 d . . . H5 H 0.9626 1.0891 0.2778 0.062 Uiso 1 1 calc R . . N1 N 0.5948(8) 0.4815(6) 0.1879(3) 0.0801(17) Uani 1 1 d . . . C8 C 0.7281(8) 0.8218(6) 0.3756(3) 0.0597(15) Uani 1 1 d . . . H8 H 0.6699 0.7538 0.4004 0.072 Uiso 1 1 calc R . . N3 N 0.6564(8) 0.2439(5) 0.0171(2) 0.0619(13) Uani 1 1 d D . . C23 C 0.4976(8) 0.0835(5) 0.1062(2) 0.0469(13) Uani 1 1 d . . . N4 N 0.3468(7) 0.3616(6) 0.4375(2) 0.0715(16) Uani 1 1 d . . . C24 C 0.6630(8) 0.0735(5) 0.0782(3) 0.0519(14) Uani 1 1 d . . . H24 H 0.7221 0.0120 0.0904 0.062 Uiso 1 1 calc R . . O7 O 0.2855(7) 0.4192(5) 0.4918(2) 0.0986(17) Uani 1 1 d . . . C27 C 0.3545(8) 0.0718(6) 0.2178(3) 0.0570(15) Uani 1 1 d . . . H27A H 0.2689 0.1211 0.2059 0.068 Uiso 1 1 calc R . . H27B H 0.2835 0.0033 0.2434 0.068 Uiso 1 1 calc R . . C28 C 0.5288(8) 0.1784(6) 0.2598(3) 0.0598(15) Uani 1 1 d . . . H28A H 0.6191 0.1310 0.2695 0.072 Uiso 1 1 calc R . . H28B H 0.5944 0.2516 0.2357 0.072 Uiso 1 1 calc R . . C22 C 0.4147(8) 0.1780(6) 0.0879(3) 0.0573(15) Uani 1 1 d . . . H22 H 0.3030 0.1871 0.1061 0.069 Uiso 1 1 calc R . . C30 C 0.4147(9) 0.3651(7) 0.3280(3) 0.0642(16) Uani 1 1 d . . . H30 H 0.4164 0.4074 0.2918 0.077 Uiso 1 1 calc R . . C25 C 0.7418(8) 0.1537(6) 0.0324(3) 0.0591(16) Uani 1 1 d . . . H25 H 0.8516 0.1454 0.0125 0.071 Uiso 1 1 calc R . . C26 C 0.4074(9) -0.0073(6) 0.1559(3) 0.0615(16) Uani 1 1 d . . . H26A H 0.4976 -0.0528 0.1681 0.074 Uiso 1 1 calc R . . H26B H 0.2909 -0.0816 0.1351 0.074 Uiso 1 1 calc R . . C31 C 0.3565(9) 0.4228(7) 0.3852(3) 0.0715(17) Uani 1 1 d . . . H31 H 0.3237 0.5048 0.3876 0.086 Uiso 1 1 calc R . . C21 C 0.4978(9) 0.2579(6) 0.0429(3) 0.0604(16) Uani 1 1 d . . . H21 H 0.4431 0.3217 0.0304 0.073 Uiso 1 1 calc R . . C29 C 0.4709(8) 0.2461(6) 0.3227(3) 0.0554(15) Uani 1 1 d . . . C32 C 0.4629(10) 0.1900(7) 0.3788(3) 0.0742(18) Uani 1 1 d . . . H32 H 0.4997 0.1102 0.3784 0.089 Uiso 1 1 calc R . . C33 C 0.4023(11) 0.2489(8) 0.4350(3) 0.084(2) Uani 1 1 d . . . H33 H 0.4001 0.2090 0.4720 0.100 Uiso 1 1 calc R . . H6A H -0.060(8) 0.664(8) 0.493(5) 0.16(4) Uiso 1 1 d D . . H3 H 0.702(9) 0.296(7) -0.014(3) 0.11(3) Uiso 1 1 d D . . H1 H 0.803(9) 0.592(7) 0.0131(13) 0.08(2) Uiso 1 1 d D . . H3B H 0.838(10) 1.087(2) 0.476(4) 0.12(3) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O5 0.098(3) 0.046(2) 0.031(2) -0.0027(17) 0.0132(18) 0.0152(19) O4 0.122(3) 0.043(2) 0.034(2) 0.0079(18) 0.019(2) 0.010(2) O6 0.093(3) 0.072(3) 0.031(2) -0.010(2) 0.019(2) 0.007(2) C20 0.071(4) 0.050(4) 0.027(3) 0.004(2) 0.010(2) 0.020(3) C12 0.063(3) 0.039(3) 0.031(3) 0.006(2) 0.009(2) 0.017(2) C13 0.066(3) 0.045(3) 0.034(3) 0.007(2) 0.009(2) 0.012(2) C19 0.072(4) 0.042(3) 0.033(3) -0.009(2) 0.006(2) 0.010(2) C14 0.066(3) 0.049(3) 0.032(3) 0.004(2) 0.013(2) 0.013(3) C16 0.083(4) 0.047(3) 0.045(4) -0.009(3) 0.014(3) 0.004(3) C18 0.068(4) 0.049(3) 0.033(3) 0.002(2) 0.015(2) 0.008(3) C11 0.066(3) 0.046(3) 0.027(3) 0.004(2) 0.009(2) 0.019(3) N2 0.109(4) 0.054(3) 0.055(3) 0.019(3) 0.016(3) 0.020(3) C17 0.073(4) 0.053(3) 0.026(3) -0.003(2) 0.011(2) 0.014(3) C15 0.077(4) 0.049(3) 0.036(3) -0.004(3) 0.016(3) 0.006(3) O1 0.097(3) 0.052(2) 0.028(2) -0.0058(19) 0.012(2) 0.016(2) O2 0.104(3) 0.049(2) 0.034(2) 0.0052(18) 0.0197(19) 0.012(2) C3 0.055(3) 0.049(3) 0.032(3) 0.005(2) 0.010(2) 0.016(2) O3 0.118(4) 0.065(3) 0.031(2) -0.003(2) 0.019(2) 0.007(3) C2 0.054(3) 0.050(3) 0.030(3) 0.007(2) 0.009(2) 0.016(2) C6 0.073(4) 0.043(3) 0.035(3) -0.006(2) 0.007(2) 0.010(3) C4 0.051(3) 0.049(3) 0.028(3) 0.000(2) 0.002(2) 0.015(2) C10 0.075(4) 0.049(4) 0.029(3) 0.000(3) 0.006(3) 0.010(3) C1 0.061(3) 0.050(3) 0.034(3) 0.002(3) 0.008(2) 0.017(2) C9 0.076(4) 0.047(3) 0.037(3) -0.001(3) 0.010(3) 0.005(3) C7 0.063(3) 0.055(3) 0.026(3) -0.002(2) 0.006(2) 0.014(3) C5 0.075(4) 0.044(3) 0.031(3) 0.004(2) 0.011(2) 0.016(3) N1 0.119(5) 0.056(3) 0.042(3) 0.007(3) 0.008(3) -0.002(3) C8 0.083(4) 0.049(3) 0.037(3) 0.006(3) 0.017(3) 0.008(3) N3 0.086(4) 0.049(3) 0.037(3) 0.003(2) 0.009(3) 0.006(3) C23 0.071(4) 0.033(3) 0.029(3) -0.002(2) 0.004(2) 0.011(2) N4 0.076(4) 0.073(4) 0.041(3) -0.010(3) 0.020(2) 0.001(3) C24 0.067(4) 0.043(3) 0.041(3) 0.002(3) 0.007(3) 0.014(2) O7 0.098(3) 0.102(4) 0.059(3) -0.024(3) 0.033(2) 0.002(3) C27 0.074(4) 0.054(3) 0.037(3) 0.009(3) 0.013(3) 0.013(3) C28 0.068(4) 0.066(4) 0.038(3) 0.006(3) 0.011(3) 0.013(3) C22 0.071(4) 0.053(3) 0.047(3) 0.005(3) 0.013(3) 0.021(3) C30 0.082(4) 0.065(4) 0.046(4) 0.011(3) 0.016(3) 0.025(3) C25 0.058(3) 0.063(4) 0.046(4) 0.000(3) 0.012(3) 0.011(3) C26 0.088(4) 0.047(3) 0.041(3) 0.002(3) 0.016(3) 0.013(3) C31 0.083(4) 0.063(4) 0.063(4) 0.004(3) 0.016(3) 0.020(3) C21 0.081(4) 0.049(3) 0.054(4) 0.014(3) 0.007(3) 0.024(3) C29 0.059(3) 0.057(4) 0.038(3) 0.001(3) 0.010(2) 0.007(3) C32 0.111(5) 0.070(4) 0.044(4) 0.013(3) 0.021(3) 0.031(4) C33 0.123(6) 0.081(5) 0.043(4) 0.017(4) 0.020(4) 0.025(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O5 C11 1.259(6) . ? O4 C11 1.233(6) . ? O6 C17 1.352(6) . ? C20 C12 1.435(8) . ? C20 N2 1.134(7) . ? C12 C13 1.335(7) . ? C12 C11 1.510(7) . ? C13 C14 1.458(7) . ? C19 C14 1.400(7) . ? C19 C18 1.375(7) . ? C14 C15 1.388(7) . ? C16 C17 1.387(8) . ? C16 C15 1.371(8) . ? C18 C17 1.392(7) . ? O1 C1 1.298(6) . ? O2 C1 1.223(6) . ? C3 C2 1.334(7) . ? C3 C4 1.467(7) . ? O3 C7 1.357(6) . ? C2 C10 1.432(8) . ? C2 C1 1.494(7) . ? C6 C7 1.393(7) . ? C6 C5 1.370(7) . ? C4 C9 1.387(7) . ? C4 C5 1.394(7) . ? C10 N1 1.152(7) . ? C9 C8 1.370(7) . ? C7 C8 1.382(7) . ? N3 C25 1.336(8) . ? N3 C21 1.323(8) . ? C23 C24 1.375(7) . ? C23 C22 1.386(8) . ? C23 C26 1.524(7) . ? N4 O7 1.337(6) . ? N4 C31 1.338(8) . ? N4 C33 1.323(9) . ? C24 C25 1.377(8) . ? C27 C28 1.518(8) . ? C27 C26 1.524(8) . ? C28 C29 1.505(7) . ? C22 C21 1.370(8) . ? C30 C31 1.373(8) . ? C30 C29 1.381(8) . ? C29 C32 1.382(8) . ? C32 C33 1.369(9) . ? 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 N2 C20 C12 177.3(6) . . ? C20 C12 C11 116.3(4) . . ? C13 C12 C20 122.6(5) . . ? C13 C12 C11 121.0(4) . . ? C12 C13 C14 131.4(5) . . ? C18 C19 C14 122.0(5) . . ? C19 C14 C13 125.6(5) . . ? C15 C14 C13 117.6(5) . . ? C15 C14 C19 116.8(5) . . ? C15 C16 C17 120.7(5) . . ? C19 C18 C17 119.9(5) . . ? O5 C11 C12 115.0(5) . . ? O4 C11 O5 126.7(5) . . ? O4 C11 C12 118.3(4) . . ? O6 C17 C16 119.0(5) . . ? O6 C17 C18 122.2(5) . . ? C16 C17 C18 118.7(5) . . ? C16 C15 C14 121.9(5) . . ? C2 C3 C4 131.6(5) . . ? C3 C2 C10 124.7(5) . . ? C3 C2 C1 119.4(5) . . ? C10 C2 C1 115.9(4) . . ? C5 C6 C7 119.5(5) . . ? C9 C4 C3 125.3(5) . . ? C9 C4 C5 117.4(5) . . ? C5 C4 C3 117.3(5) . . ? N1 C10 C2 178.4(7) . . ? O1 C1 C2 113.3(5) . . ? O2 C1 O1 125.3(5) . . ? O2 C1 C2 121.5(5) . . ? C8 C9 C4 121.4(5) . . ? O3 C7 C6 122.8(5) . . ? O3 C7 C8 117.9(5) . . ? C8 C7 C6 119.2(5) . . ? C6 C5 C4 121.9(5) . . ? C9 C8 C7 120.5(5) . . ? C21 N3 C25 123.4(5) . . ? C24 C23 C22 118.3(5) . . ? C24 C23 C26 120.9(5) . . ? C22 C23 C26 120.8(5) . . ? O7 N4 C31 118.5(6) . . ? C33 N4 O7 121.6(6) . . ? C33 N4 C31 119.8(6) . . ? C23 C24 C25 120.6(5) . . ? C28 C27 C26 113.7(5) . . ? C29 C28 C27 111.8(5) . . ? C21 C22 C23 119.8(5) . . ? C31 C30 C29 122.0(6) . . ? N3 C25 C24 118.3(5) . . ? C23 C26 C27 115.4(4) . . ? N4 C31 C30 120.3(6) . . ? N3 C21 C22 119.6(5) . . ? C30 C29 C28 122.8(5) . . ? C30 C29 C32 115.0(5) . . ? C32 C29 C28 122.2(6) . . ? C33 C32 C29 121.8(7) . . ? N4 C33 C32 121.1(7) . . ? _database_code_depnum_ccdc_archive 'CCDC 974286' ####################################################################### # # 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_BPO-phba _audit_creation_date 2012-10-10 _audit_creation_method ; Olex2 1.2 (compiled 2012.05.09 svn.r2324, GUI svn.r4230) ; _chemical_name_common 'BPO.4-hydroxybenzoic acid' _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C10 H8 N2 O, C7 H6 O3' _chemical_formula_sum 'C17 H14 N2 O4' _chemical_formula_weight 310.30 _chemical_melting_point ? 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' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 6.4902(17) _cell_length_b 7.288(2) _cell_length_c 16.056(3) _cell_angle_alpha 88.34(2) _cell_angle_beta 78.438(19) _cell_angle_gamma 73.56(3) _cell_volume 713.3(3) _cell_formula_units_Z 2 _cell_measurement_reflns_used 938 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 29.1438 _cell_measurement_theta_min 2.5856 _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.50642 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.445 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 324 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.24 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0472 _diffrn_reflns_av_unetI/netI 0.0964 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 6047 _diffrn_reflns_theta_full 24.99 _diffrn_reflns_theta_max 24.99 _diffrn_reflns_theta_min 2.59 _diffrn_ambient_temperature 298(2) _diffrn_detector_area_resol_mean 15.9821 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -11.00 86.00 1.0000 12.2400 omega____ theta____ kappa____ phi______ frames - 18.9803 77.0000 -150.0000 97 #__ type_ start__ end____ width___ exp.time_ 2 omega -49.00 -13.00 1.0000 12.2400 omega____ theta____ kappa____ phi______ frames - 18.9803 -77.0000 -30.0000 36 #__ type_ start__ end____ width___ exp.time_ 3 omega -10.00 89.00 1.0000 12.2400 omega____ theta____ kappa____ phi______ frames - 18.9803 77.0000 0.0000 99 #__ type_ start__ end____ width___ exp.time_ 4 omega 19.00 89.00 1.0000 12.2400 omega____ theta____ kappa____ phi______ frames - 18.9803 77.0000 -120.0000 70 #__ type_ start__ end____ width___ exp.time_ 5 omega -47.00 47.00 1.0000 12.2400 omega____ theta____ kappa____ phi______ frames - 18.9803 -77.0000 90.0000 94 #__ type_ start__ end____ width___ exp.time_ 6 omega -94.00 -69.00 1.0000 12.2400 omega____ theta____ kappa____ phi______ frames - -17.3397 179.0000 -120.0000 25 #__ type_ start__ end____ width___ exp.time_ 7 omega -94.00 -32.00 1.0000 12.2400 omega____ theta____ kappa____ phi______ frames - -17.3397 179.0000 120.0000 62 ; _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0724680000 _diffrn_orient_matrix_UB_12 0.0538751000 _diffrn_orient_matrix_UB_13 -0.0252922000 _diffrn_orient_matrix_UB_21 0.0671359000 _diffrn_orient_matrix_UB_22 -0.0533568000 _diffrn_orient_matrix_UB_23 -0.0367246000 _diffrn_orient_matrix_UB_31 -0.0613913000 _diffrn_orient_matrix_UB_32 -0.0674992000 _diffrn_orient_matrix_UB_33 0.0068336000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 1015 _reflns_number_total 2514 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; SHELXS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.240 _refine_diff_density_min -0.231 _refine_diff_density_rms 0.045 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.972 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 216 _refine_ls_number_reflns 2514 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1789 _refine_ls_R_factor_gt 0.0616 _refine_ls_restrained_S_all 0.972 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0523P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1182 _refine_ls_wR_factor_ref 0.1693 _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. DFIX 0.85 0.01 O3 H3 O1 H1 ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 N2 N 1.4770(5) -0.1780(4) 0.07484(19) 0.0460(9) Uani 1 1 d . . . O3 O 0.0013(4) 0.7203(4) 0.96224(17) 0.0619(9) Uani 1 1 d D . . C10 C 1.1199(5) 0.0574(5) 0.3190(2) 0.0384(10) Uani 1 1 d . . . C16 C 1.4614(5) -0.0301(5) 0.2055(2) 0.0498(11) Uani 1 1 d . . . H16 H 1.5330 0.0184 0.2405 0.060 Uiso 1 1 calc R . . C2 C 0.3244(5) 0.4759(5) 0.7249(2) 0.0380(10) Uani 1 1 d . . . O2 O 0.3714(4) 0.2878(4) 0.60036(17) 0.0704(10) Uani 1 1 d . . . O1 O 0.6369(4) 0.4116(4) 0.61696(17) 0.0672(9) Uani 1 1 d D . . C14 C 1.1522(5) -0.1046(6) 0.1793(2) 0.0544(12) Uani 1 1 d . . . H14 H 1.0071 -0.1067 0.1955 0.065 Uiso 1 1 calc R . . C4 C 0.3204(5) 0.6284(5) 0.8565(2) 0.0492(11) Uani 1 1 d . . . H4 H 0.3948 0.6748 0.8910 0.059 Uiso 1 1 calc R . . C6 C -0.0062(5) 0.5658(5) 0.8330(2) 0.0452(11) Uani 1 1 d . . . H6 H -0.1533 0.5718 0.8514 0.054 Uiso 1 1 calc R . . C12 C 1.0690(6) 0.2537(6) 0.4428(2) 0.0568(12) Uani 1 1 d . . . H12 H 1.1250 0.3285 0.4731 0.068 Uiso 1 1 calc R . . C11 C 1.1944(5) 0.1688(5) 0.3668(2) 0.0490(11) Uani 1 1 d . . . H11 H 1.3319 0.1871 0.3475 0.059 Uiso 1 1 calc R . . O4 O 1.5843(4) -0.2478(4) -0.00177(15) 0.0655(9) Uani 1 1 d . . . C9 C 0.9156(5) 0.0332(5) 0.3536(2) 0.0509(11) Uani 1 1 d . . . H9 H 0.8578 -0.0441 0.3254 0.061 Uiso 1 1 calc R . . C8 C 0.7992(6) 0.1237(6) 0.4294(3) 0.0572(12) Uani 1 1 d . . . H8 H 0.6614 0.1072 0.4503 0.069 Uiso 1 1 calc R . . C17 C 1.5725(6) -0.1024(6) 0.1267(2) 0.0521(12) Uani 1 1 d . . . H17 H 1.7169 -0.0995 0.1085 0.063 Uiso 1 1 calc R . . C5 C 0.1011(5) 0.6383(5) 0.8847(2) 0.0431(10) Uani 1 1 d . . . C13 C 1.2686(6) -0.1782(6) 0.1016(2) 0.0570(12) Uani 1 1 d . . . H13 H 1.2012 -0.2301 0.0661 0.068 Uiso 1 1 calc R . . C15 C 1.2445(5) -0.0268(5) 0.2349(2) 0.0403(10) Uani 1 1 d . . . C7 C 0.1053(5) 0.4845(5) 0.7543(2) 0.0459(11) Uani 1 1 d . . . H7 H 0.0324 0.4346 0.7204 0.055 Uiso 1 1 calc R . . C3 C 0.4274(6) 0.5499(5) 0.7775(2) 0.0479(11) Uani 1 1 d . . . H3A H 0.5737 0.5464 0.7588 0.058 Uiso 1 1 calc R . . N1 N 0.8708(5) 0.2335(5) 0.47484(19) 0.0548(10) Uani 1 1 d . . . C1 C 0.4423(6) 0.3833(6) 0.6420(2) 0.0473(11) Uani 1 1 d . . . H3 H -0.134(2) 0.726(6) 0.972(2) 0.103(19) Uiso 1 1 d D . . H1 H 0.708(5) 0.349(5) 0.5701(14) 0.082(15) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N2 0.040(2) 0.063(2) 0.0311(19) -0.0050(18) -0.0026(15) -0.0104(17) O3 0.0476(19) 0.090(2) 0.0439(18) -0.0263(16) 0.0035(14) -0.0193(16) C10 0.037(2) 0.043(3) 0.033(2) -0.004(2) -0.0057(17) -0.0078(19) C16 0.048(2) 0.065(3) 0.039(3) -0.014(2) -0.0057(19) -0.021(2) C2 0.038(2) 0.041(3) 0.032(2) -0.003(2) -0.0014(17) -0.0093(18) O2 0.0651(19) 0.091(2) 0.058(2) -0.0317(19) 0.0012(15) -0.0328(17) O1 0.0578(19) 0.092(3) 0.050(2) -0.0257(19) 0.0130(15) -0.0335(18) C14 0.037(2) 0.083(3) 0.045(3) -0.011(2) -0.0035(19) -0.023(2) C4 0.044(2) 0.068(3) 0.039(2) -0.011(2) -0.0050(19) -0.023(2) C6 0.033(2) 0.056(3) 0.043(3) -0.008(2) -0.0043(18) -0.0096(19) C12 0.063(3) 0.062(3) 0.045(3) -0.012(2) 0.001(2) -0.024(2) C11 0.046(2) 0.063(3) 0.038(2) -0.010(2) 0.0002(18) -0.019(2) O4 0.0512(16) 0.104(2) 0.0354(16) -0.0248(17) 0.0021(12) -0.0180(15) C9 0.040(2) 0.066(3) 0.045(3) -0.015(2) -0.0037(19) -0.016(2) C8 0.041(2) 0.076(4) 0.051(3) -0.001(3) 0.000(2) -0.017(2) C17 0.038(2) 0.078(3) 0.044(3) -0.012(2) -0.0043(19) -0.022(2) C5 0.041(2) 0.050(3) 0.035(2) -0.008(2) -0.0035(18) -0.0095(19) C13 0.044(2) 0.090(4) 0.042(3) -0.010(3) -0.007(2) -0.028(2) C15 0.034(2) 0.046(3) 0.040(2) -0.002(2) -0.0071(18) -0.0093(18) C7 0.040(2) 0.053(3) 0.047(3) -0.010(2) -0.0110(18) -0.0128(19) C3 0.038(2) 0.064(3) 0.042(3) -0.003(2) -0.0016(18) -0.019(2) N1 0.052(2) 0.065(3) 0.041(2) -0.0079(19) 0.0016(16) -0.0128(19) C1 0.045(2) 0.055(3) 0.040(3) -0.001(2) -0.004(2) -0.013(2) _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 N2 O4 1.322(3) . ? N2 C17 1.345(4) . ? N2 C13 1.335(4) . ? O3 C5 1.351(4) . ? C10 C11 1.374(5) . ? C10 C9 1.389(4) . ? C10 C15 1.478(4) . ? C16 C17 1.362(4) . ? C16 C15 1.386(4) . ? C2 C7 1.390(4) . ? C2 C3 1.382(4) . ? C2 C1 1.471(4) . ? O2 C1 1.214(4) . ? O1 C1 1.319(4) . ? C14 C13 1.358(4) . ? C14 C15 1.383(5) . ? C4 C5 1.386(4) . ? C4 C3 1.372(4) . ? C6 C5 1.385(5) . ? C6 C7 1.381(4) . ? C12 C11 1.376(4) . ? C12 N1 1.334(4) . ? C9 C8 1.372(5) . ? C8 N1 1.330(4) . ? 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 O4 N2 C17 121.2(3) . . ? O4 N2 C13 120.2(3) . . ? C13 N2 C17 118.5(3) . . ? C11 C10 C9 115.7(3) . . ? C11 C10 C15 122.5(3) . . ? C9 C10 C15 121.7(3) . . ? C17 C16 C15 121.8(4) . . ? C7 C2 C1 120.4(3) . . ? C3 C2 C7 117.7(3) . . ? C3 C2 C1 121.9(3) . . ? C13 C14 C15 121.6(3) . . ? C3 C4 C5 119.8(3) . . ? C7 C6 C5 120.0(3) . . ? N1 C12 C11 122.9(4) . . ? C10 C11 C12 121.1(4) . . ? C8 C9 C10 119.8(4) . . ? N1 C8 C9 124.2(4) . . ? N2 C17 C16 121.1(3) . . ? O3 C5 C4 117.7(3) . . ? O3 C5 C6 123.0(3) . . ? C6 C5 C4 119.3(3) . . ? N2 C13 C14 121.8(4) . . ? C16 C15 C10 122.3(3) . . ? C14 C15 C10 122.5(3) . . ? C14 C15 C16 115.2(3) . . ? C6 C7 C2 121.2(3) . . ? C4 C3 C2 122.0(3) . . ? C8 N1 C12 116.1(3) . . ? O2 C1 C2 124.2(4) . . ? O2 C1 O1 122.5(4) . . ? O1 C1 C2 113.3(4) . . ? _database_code_depnum_ccdc_archive 'CCDC 974287' ####################################################################### # # 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_BPO-acca _audit_creation_date 2012-10-10 _audit_creation_method ; Olex2 1.2 (compiled 2012.05.09 svn.r2324, GUI svn.r4230) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C10 H8 N2 O, C10 H7 N O3' _chemical_formula_sum 'C20 H15 N3 O4' _chemical_formula_weight 361.35 _chemical_absolute_configuration unk _chemical_melting_point ? 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' _space_group_crystal_system monoclinic _space_group_IT_number 9 _space_group_name_H-M_alt 'C 1 c 1' _space_group_name_Hall 'C -2yc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 'x, -y, z+1/2' 3 'x+1/2, y+1/2, z' 4 'x+1/2, -y+1/2, z+1/2' _cell_length_a 13.3286(4) _cell_length_b 10.7445(3) _cell_length_c 12.3344(4) _cell_angle_alpha 90.00 _cell_angle_beta 102.018(3) _cell_angle_gamma 90.00 _cell_volume 1727.68(9) _cell_formula_units_Z 4 _cell_measurement_reflns_used 3936 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 28.2187 _cell_measurement_theta_min 3.1189 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.78484 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour ? _exptl_crystal_density_diffrn 1.389 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description ? _exptl_crystal_F_000 752 _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_min 0.42 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0116 _diffrn_reflns_av_unetI/netI 0.0152 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 4719 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 28.28 _diffrn_reflns_theta_min 3.13 _diffrn_ambient_temperature 298(2) _diffrn_detector_area_resol_mean 15.9821 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.894 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega 18.00 76.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 26.4848 77.0000 -30.0000 58 #__ type_ start__ end____ width___ exp.time_ 2 omega 13.00 86.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 26.4848 77.0000 150.0000 73 #__ type_ start__ end____ width___ exp.time_ 3 omega -13.00 106.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 26.4848 77.0000 90.0000 119 #__ type_ start__ end____ width___ exp.time_ 4 omega 34.00 63.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 26.4848 179.0000 -30.0000 29 #__ type_ start__ end____ width___ exp.time_ 5 omega 34.00 116.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 26.4848 179.0000 -180.0000 82 ; _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0255391000 _diffrn_orient_matrix_UB_12 0.0447522000 _diffrn_orient_matrix_UB_13 -0.0268743000 _diffrn_orient_matrix_UB_21 0.0443921000 _diffrn_orient_matrix_UB_22 -0.0057754000 _diffrn_orient_matrix_UB_23 0.0428180000 _diffrn_orient_matrix_UB_31 0.0183455000 _diffrn_orient_matrix_UB_32 -0.0482099000 _diffrn_orient_matrix_UB_33 -0.0299934000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 2917 _reflns_number_total 3124 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; SHELXS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.150 _refine_diff_density_min -0.197 _refine_diff_density_rms 0.047 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1.0(9) _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 252 _refine_ls_number_reflns 3124 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0370 _refine_ls_R_factor_gt 0.0338 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0497P)^2^+0.4260P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0851 _refine_ls_wR_factor_ref 0.0883 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 C18 C 0.60284(11) 0.33148(16) 0.41159(13) 0.0338(4) Uani 1 1 d . . . O2 O 0.13627(11) 0.17907(16) 0.56105(12) 0.0607(4) Uani 1 1 d . . . C2 C 0.26160(12) 0.12477(16) 0.45659(14) 0.0348(4) Uani 1 1 d . . . N2 N 0.40316(10) 0.40212(13) 0.41694(13) 0.0404(4) Uani 1 1 d . . . O1 O 0.09007(10) 0.16535(15) 0.37706(12) 0.0528(4) Uani 1 1 d D . . C12 C 0.78815(13) 0.29974(18) 0.49912(15) 0.0415(4) Uani 1 1 d . . . H12 H 0.7766 0.3323 0.5653 0.050 Uiso 1 1 calc R . . N1 N 0.90626(10) 0.21390(14) 0.39921(13) 0.0423(4) Uani 1 1 d . . . C4 C 0.33815(12) 0.11307(17) 0.54566(15) 0.0377(4) Uani 1 1 d . . . H4 H 0.3195 0.1290 0.6129 0.045 Uiso 1 1 calc R . . C5 C 0.44559(12) 0.07975(16) 0.55521(14) 0.0354(4) Uani 1 1 d . . . C13 C 0.70802(11) 0.28945(15) 0.40775(13) 0.0320(3) Uani 1 1 d . . . O3 O 0.75711(10) 0.00051(15) 0.60328(13) 0.0561(4) Uani 1 1 d D . . C19 C 0.52762(14) 0.34451(19) 0.31512(16) 0.0471(5) Uani 1 1 d . . . H19 H 0.5443 0.3301 0.2466 0.057 Uiso 1 1 calc R . . C9 C 0.59141(13) 0.01142(17) 0.48219(16) 0.0407(4) Uani 1 1 d . . . H9 H 0.6181 -0.0167 0.4227 0.049 Uiso 1 1 calc R . . C1 C 0.15589(12) 0.16019(17) 0.47167(16) 0.0393(4) Uani 1 1 d . . . O4 O 0.30789(10) 0.43135(14) 0.41897(13) 0.0566(4) Uani 1 1 d . . . C8 C 0.65552(12) 0.02458(18) 0.58567(15) 0.0412(4) Uani 1 1 d . . . C16 C 0.47512(14) 0.39587(19) 0.51157(16) 0.0458(4) Uani 1 1 d . . . H16 H 0.4574 0.4152 0.5787 0.055 Uiso 1 1 calc R . . C15 C 0.82951(13) 0.20123(18) 0.31254(16) 0.0453(4) Uani 1 1 d . . . H15 H 0.8433 0.1663 0.2482 0.054 Uiso 1 1 calc R . . C17 C 0.57420(13) 0.36135(18) 0.51033(15) 0.0417(4) Uani 1 1 d . . . H17 H 0.6226 0.3580 0.5765 0.050 Uiso 1 1 calc R . . C6 C 0.51162(14) 0.0907(2) 0.65916(15) 0.0474(5) Uani 1 1 d . . . H6 H 0.4850 0.1157 0.7196 0.057 Uiso 1 1 calc R . . C11 C 0.88508(13) 0.26138(19) 0.49135(16) 0.0445(4) Uani 1 1 d . . . H11 H 0.9380 0.2691 0.5534 0.053 Uiso 1 1 calc R . . C7 C 0.61495(14) 0.0653(2) 0.67424(16) 0.0521(5) Uani 1 1 d . . . H7 H 0.6574 0.0756 0.7437 0.063 Uiso 1 1 calc R . . C10 C 0.48888(13) 0.03956(18) 0.46693(15) 0.0409(4) Uani 1 1 d . . . H10 H 0.4474 0.0318 0.3967 0.049 Uiso 1 1 calc R . . C20 C 0.42939(14) 0.3783(2) 0.31979(17) 0.0500(5) Uani 1 1 d . . . H20 H 0.3801 0.3849 0.2545 0.060 Uiso 1 1 calc R . . C3 C 0.27128(14) 0.1058(2) 0.34447(17) 0.0465(4) Uani 1 1 d . . . C14 C 0.73018(13) 0.23711(18) 0.31255(15) 0.0420(4) Uani 1 1 d . . . H14 H 0.6787 0.2264 0.2496 0.050 Uiso 1 1 calc R . . N3 N 0.27897(16) 0.0901(3) 0.25552(17) 0.0788(7) Uani 1 1 d . . . H1 H 0.0253(15) 0.180(2) 0.390(2) 0.077(8) Uiso 1 1 d D . . H3 H 0.771(2) -0.025(3) 0.5423(19) 0.082(9) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C18 0.0278(8) 0.0365(8) 0.0352(9) 0.0026(7) 0.0025(7) 0.0005(6) O2 0.0386(7) 0.0990(12) 0.0450(9) -0.0136(8) 0.0100(6) 0.0166(7) C2 0.0273(7) 0.0401(8) 0.0374(9) 0.0022(7) 0.0076(7) 0.0034(6) N2 0.0274(7) 0.0457(8) 0.0480(10) 0.0043(7) 0.0080(7) 0.0059(6) O1 0.0288(6) 0.0824(10) 0.0451(8) -0.0005(7) 0.0032(6) 0.0133(6) C12 0.0326(8) 0.0567(11) 0.0342(9) -0.0044(8) 0.0045(7) 0.0038(7) N1 0.0268(6) 0.0492(8) 0.0505(9) 0.0010(7) 0.0072(6) 0.0059(6) C4 0.0301(8) 0.0478(10) 0.0353(9) -0.0014(7) 0.0073(7) 0.0046(7) C5 0.0255(7) 0.0443(9) 0.0357(9) 0.0034(7) 0.0048(6) 0.0040(6) C13 0.0277(7) 0.0348(8) 0.0327(9) 0.0036(6) 0.0045(6) 0.0018(6) O3 0.0272(6) 0.0908(11) 0.0481(8) 0.0081(8) 0.0029(6) 0.0109(6) C19 0.0342(9) 0.0709(12) 0.0349(10) -0.0018(9) 0.0044(8) 0.0108(8) C9 0.0320(8) 0.0539(10) 0.0382(10) -0.0010(8) 0.0117(7) 0.0038(7) C1 0.0275(8) 0.0442(9) 0.0445(11) -0.0018(8) 0.0038(7) 0.0050(7) O4 0.0271(6) 0.0775(10) 0.0660(10) 0.0036(8) 0.0119(6) 0.0115(6) C8 0.0283(8) 0.0545(10) 0.0400(10) 0.0085(8) 0.0054(7) 0.0037(7) C16 0.0379(10) 0.0622(12) 0.0385(10) 0.0010(9) 0.0108(8) 0.0068(8) C15 0.0377(9) 0.0582(11) 0.0412(11) -0.0044(8) 0.0111(8) 0.0098(8) C17 0.0310(8) 0.0567(10) 0.0356(9) 0.0044(8) 0.0026(7) 0.0046(7) C6 0.0363(9) 0.0734(13) 0.0325(9) 0.0006(9) 0.0070(7) 0.0078(9) C11 0.0317(9) 0.0556(11) 0.0423(10) 0.0006(8) -0.0011(8) 0.0034(8) C7 0.0355(9) 0.0850(14) 0.0324(10) 0.0064(10) -0.0012(7) 0.0058(9) C10 0.0326(8) 0.0546(10) 0.0337(9) -0.0034(8) 0.0030(7) 0.0028(7) C20 0.0328(9) 0.0729(13) 0.0400(11) -0.0003(9) -0.0027(8) 0.0101(9) C3 0.0296(8) 0.0686(12) 0.0411(11) 0.0094(9) 0.0064(7) 0.0097(8) C14 0.0295(8) 0.0575(11) 0.0363(9) -0.0031(8) 0.0006(7) 0.0061(7) N3 0.0551(11) 0.144(2) 0.0379(11) 0.0085(11) 0.0103(9) 0.0222(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C18 C13 1.483(2) . ? C18 C19 1.394(2) . ? C18 C17 1.388(2) . ? O2 C1 1.202(2) . ? C2 C4 1.341(2) . ? C2 C1 1.508(2) . ? C2 C3 1.430(3) . ? N2 O4 1.3133(18) . ? N2 C16 1.349(2) . ? N2 C20 1.341(3) . ? O1 C1 1.307(2) . ? C12 C13 1.386(2) . ? C12 C11 1.378(2) . ? N1 C15 1.324(2) . ? N1 C11 1.329(2) . ? C4 C5 1.457(2) . ? C5 C6 1.401(2) . ? C5 C10 1.402(2) . ? C13 C14 1.388(2) . ? O3 C8 1.351(2) . ? C19 C20 1.371(3) . ? C9 C8 1.388(3) . ? C9 C10 1.374(2) . ? C8 C7 1.387(3) . ? C16 C17 1.375(2) . ? C15 C14 1.379(2) . ? C6 C7 1.378(2) . ? C3 N3 1.135(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C19 C18 C13 121.33(15) . . ? C17 C18 C13 122.21(14) . . ? C17 C18 C19 116.46(15) . . ? C4 C2 C1 119.60(16) . . ? C4 C2 C3 124.93(16) . . ? C3 C2 C1 115.47(15) . . ? O4 N2 C16 120.76(16) . . ? O4 N2 C20 119.71(15) . . ? C20 N2 C16 119.53(15) . . ? C11 C12 C13 119.62(17) . . ? C15 N1 C11 117.66(15) . . ? C2 C4 C5 131.07(17) . . ? C6 C5 C4 118.24(15) . . ? C6 C5 C10 117.05(15) . . ? C10 C5 C4 124.70(15) . . ? C12 C13 C18 121.55(15) . . ? C12 C13 C14 117.15(15) . . ? C14 C13 C18 121.30(14) . . ? C20 C19 C18 120.92(18) . . ? C10 C9 C8 120.55(17) . . ? O2 C1 C2 122.88(16) . . ? O2 C1 O1 125.31(16) . . ? O1 C1 C2 111.80(16) . . ? O3 C8 C9 122.22(17) . . ? O3 C8 C7 118.42(16) . . ? C7 C8 C9 119.35(15) . . ? N2 C16 C17 121.02(17) . . ? N1 C15 C14 123.48(18) . . ? C16 C17 C18 120.83(17) . . ? C7 C6 C5 121.79(17) . . ? N1 C11 C12 122.92(17) . . ? C6 C7 C8 119.92(17) . . ? C9 C10 C5 121.32(16) . . ? N2 C20 C19 121.12(17) . . ? N3 C3 C2 179.7(3) . . ? C15 C14 C13 119.13(16) . . ? _database_code_depnum_ccdc_archive 'CCDC 974288' ####################################################################### # # 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_BPO-phba-water _audit_creation_date 2012-10-10 _audit_creation_method ; Olex2 1.2 (compiled 2012.05.09 svn.r2324, GUI svn.r4230) ; _chemical_name_common 'BPO.4-hydroxybenzoic acid.H2O' _chemical_name_systematic ? _chemical_formula_moiety 'C7 H6 O3, C10 H8 N2 O, H2 O' _chemical_formula_sum 'C17 H16 N2 O5' _chemical_formula_weight 328.32 _chemical_melting_point ? 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' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 6.8052(4) _cell_length_b 9.9004(7) _cell_length_c 12.1414(10) _cell_angle_alpha 111.542(7) _cell_angle_beta 93.418(6) _cell_angle_gamma 98.055(6) _cell_volume 747.87(10) _cell_formula_units_Z 2 _cell_measurement_reflns_used 3017 _cell_measurement_temperature 150.0 _cell_measurement_theta_max 29.0941 _cell_measurement_theta_min 3.0393 _exptl_absorpt_coefficient_mu 0.109 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.82622 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour yellowish _exptl_crystal_density_diffrn 1.458 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 344 _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.41 _exptl_crystal_size_min 0.40 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0252 _diffrn_reflns_av_unetI/netI 0.0376 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 4978 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 3.05 _diffrn_ambient_temperature 150.0 _diffrn_detector_area_resol_mean 15.9821 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -82.00 -57.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - -17.4178 -37.0000 -150.0000 25 #__ type_ start__ end____ width___ exp.time_ 2 omega -18.00 12.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - -17.4178 -103.0000 55.0000 30 #__ type_ start__ end____ width___ exp.time_ 3 omega -87.00 -33.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - -17.4178 179.0000 0.0000 54 #__ type_ start__ end____ width___ exp.time_ 4 omega -42.00 55.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - -17.4178 37.0000 30.0000 97 #__ type_ start__ end____ width___ exp.time_ 5 omega -58.00 16.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - -17.4178 103.0000 124.0000 74 #__ type_ start__ end____ width___ exp.time_ 6 omega -10.00 89.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 19.1366 77.0000 -90.0000 99 ; _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0319915000 _diffrn_orient_matrix_UB_12 -0.0692791000 _diffrn_orient_matrix_UB_13 -0.0178863000 _diffrn_orient_matrix_UB_21 -0.0075396000 _diffrn_orient_matrix_UB_22 -0.0002371000 _diffrn_orient_matrix_UB_23 0.0579464000 _diffrn_orient_matrix_UB_31 -0.1008199000 _diffrn_orient_matrix_UB_32 -0.0363225000 _diffrn_orient_matrix_UB_33 -0.0180352000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 2231 _reflns_number_total 2624 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; SHELXS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.166 _refine_diff_density_min -0.243 _refine_diff_density_rms 0.055 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 233 _refine_ls_number_reflns 2624 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0458 _refine_ls_R_factor_gt 0.0379 _refine_ls_restrained_S_all 1.062 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0473P)^2^+0.1107P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0935 _refine_ls_wR_factor_ref 0.1003 _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. DFIX 0.85 O1 H1 O3 H3 O5 H5b O5 H5a ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 O3 O -0.27307(16) 0.31947(12) 0.77822(10) 0.0274(3) Uani 1 1 d D . . O4 O 0.78701(16) 1.31396(12) 0.24366(10) 0.0274(3) Uani 1 1 d . . . N2 N 0.76697(18) 1.21487(14) 0.29400(11) 0.0203(3) Uani 1 1 d . . . O1 O 0.50111(16) 0.35168(12) 1.10869(11) 0.0294(3) Uani 1 1 d D . . O2 O 0.32937(17) 0.13533(12) 1.09348(10) 0.0302(3) Uani 1 1 d . . . C13 C 0.7973(2) 1.26047(17) 0.41384(14) 0.0209(3) Uani 1 1 d . . . H13 H 0.8287 1.3608 0.4601 0.025 Uiso 1 1 calc R . . O5 O 0.83822(18) 0.51550(13) 0.68081(11) 0.0306(3) Uani 1 1 d D . . C15 C 0.7350(2) 1.00980(16) 0.40161(13) 0.0175(3) Uani 1 1 d . . . N1 N 0.68943(19) 0.69302(15) 0.56921(12) 0.0255(3) Uani 1 1 d . . . C10 C 0.7190(2) 0.90014(16) 0.45878(13) 0.0177(3) Uani 1 1 d . . . C4 C -0.1557(2) 0.20261(16) 0.89936(14) 0.0225(4) Uani 1 1 d . . . H4 H -0.2812 0.1439 0.8841 0.027 Uiso 1 1 calc R . . C2 C 0.1829(2) 0.27250(16) 0.99618(12) 0.0182(3) Uani 1 1 d . . . C9 C 0.6765(2) 0.74884(16) 0.39265(14) 0.0214(3) Uani 1 1 d . . . H9 H 0.6570 0.7134 0.3098 0.026 Uiso 1 1 calc R . . C7 C 0.2173(2) 0.37840(16) 0.94591(13) 0.0199(3) Uani 1 1 d . . . H7 H 0.3420 0.4384 0.9622 0.024 Uiso 1 1 calc R . . C11 C 0.7455(2) 0.94363(17) 0.58287(13) 0.0223(4) Uani 1 1 d . . . H11 H 0.7734 1.0433 0.6316 0.027 Uiso 1 1 calc R . . C14 C 0.7827(2) 1.16121(16) 0.46818(13) 0.0199(3) Uani 1 1 d . . . H14 H 0.8049 1.1951 0.5509 0.024 Uiso 1 1 calc R . . C17 C 0.7192(2) 1.06980(17) 0.22570(14) 0.0231(4) Uani 1 1 d . . . H17 H 0.6975 1.0389 0.1431 0.028 Uiso 1 1 calc R . . C1 C 0.3413(2) 0.24576(16) 1.07042(13) 0.0195(3) Uani 1 1 d . . . C16 C 0.7026(2) 0.96750(17) 0.27792(13) 0.0219(4) Uani 1 1 d . . . H16 H 0.6689 0.8678 0.2298 0.026 Uiso 1 1 calc R . . C3 C -0.0060(2) 0.18510(16) 0.97176(13) 0.0211(3) Uani 1 1 d . . . H3A H -0.0312 0.1141 1.0048 0.025 Uiso 1 1 calc R . . C8 C 0.6634(2) 0.65159(18) 0.45039(15) 0.0258(4) Uani 1 1 d . . . H8 H 0.6347 0.5512 0.4040 0.031 Uiso 1 1 calc R . . C5 C -0.1200(2) 0.30770(16) 0.84898(13) 0.0195(3) Uani 1 1 d . . . C12 C 0.7301(2) 0.83868(18) 0.63273(14) 0.0248(4) Uani 1 1 d . . . H12 H 0.7490 0.8708 0.7154 0.030 Uiso 1 1 calc R . . C6 C 0.0682(2) 0.39511(16) 0.87219(13) 0.0204(3) Uani 1 1 d . . . H6 H 0.0936 0.4649 0.8380 0.024 Uiso 1 1 calc R . . H5A H 0.957(2) 0.569(2) 0.7093(18) 0.051(6) Uiso 1 1 d D . . H1 H 0.586(3) 0.331(2) 1.1561(17) 0.054(6) Uiso 1 1 d D . . H5B H 0.774(3) 0.562(2) 0.6481(19) 0.057(7) Uiso 1 1 d D . . H3 H -0.241(3) 0.390(2) 0.752(2) 0.064(7) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O3 0.0264(6) 0.0265(7) 0.0304(7) 0.0160(5) -0.0095(5) -0.0012(5) O4 0.0275(6) 0.0281(7) 0.0338(7) 0.0232(5) -0.0043(5) -0.0008(5) N2 0.0172(7) 0.0230(7) 0.0239(7) 0.0135(6) -0.0006(5) 0.0020(5) O1 0.0239(6) 0.0287(7) 0.0405(8) 0.0233(6) -0.0085(5) -0.0031(5) O2 0.0342(7) 0.0262(7) 0.0355(7) 0.0218(5) -0.0065(5) -0.0018(5) C13 0.0197(8) 0.0197(8) 0.0211(8) 0.0064(6) -0.0018(6) 0.0020(6) O5 0.0289(7) 0.0302(7) 0.0364(7) 0.0218(6) -0.0100(6) -0.0024(5) C15 0.0121(7) 0.0220(8) 0.0194(8) 0.0082(6) 0.0028(6) 0.0051(6) N1 0.0216(7) 0.0313(8) 0.0290(8) 0.0179(6) -0.0001(6) 0.0047(6) C10 0.0111(7) 0.0239(8) 0.0208(8) 0.0109(6) 0.0025(6) 0.0051(6) C4 0.0218(8) 0.0195(8) 0.0238(9) 0.0079(7) 0.0006(6) -0.0022(6) C2 0.0228(8) 0.0183(8) 0.0138(8) 0.0064(6) 0.0026(6) 0.0037(6) C9 0.0205(8) 0.0247(9) 0.0202(8) 0.0094(7) 0.0011(6) 0.0055(6) C7 0.0209(8) 0.0180(8) 0.0210(8) 0.0086(6) 0.0013(6) 0.0010(6) C11 0.0215(8) 0.0245(9) 0.0212(9) 0.0089(7) 0.0023(6) 0.0042(6) C14 0.0193(8) 0.0239(8) 0.0163(8) 0.0077(6) 0.0003(6) 0.0040(6) C17 0.0264(9) 0.0255(9) 0.0172(8) 0.0079(7) 0.0027(6) 0.0043(6) C1 0.0225(8) 0.0212(8) 0.0160(8) 0.0090(6) 0.0041(6) 0.0018(6) C16 0.0260(9) 0.0198(8) 0.0195(8) 0.0068(6) 0.0011(6) 0.0050(6) C3 0.0272(9) 0.0175(8) 0.0213(8) 0.0113(6) 0.0031(7) 0.0016(6) C8 0.0252(9) 0.0237(9) 0.0301(10) 0.0117(7) 0.0005(7) 0.0058(6) C5 0.0238(8) 0.0173(8) 0.0155(8) 0.0041(6) -0.0009(6) 0.0046(6) C12 0.0230(8) 0.0326(10) 0.0215(9) 0.0133(7) 0.0017(7) 0.0055(7) C6 0.0257(8) 0.0175(8) 0.0208(8) 0.0116(6) 0.0018(6) 0.0012(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 O3 C5 1.3555(18) . ? O4 N2 1.3294(15) . ? N2 C13 1.349(2) . ? N2 C17 1.349(2) . ? O1 C1 1.3268(18) . ? O2 C1 1.2178(17) . ? C13 C14 1.367(2) . ? C15 C10 1.484(2) . ? C15 C14 1.396(2) . ? C15 C16 1.397(2) . ? N1 C8 1.340(2) . ? N1 C12 1.340(2) . ? C10 C9 1.393(2) . ? C10 C11 1.399(2) . ? C4 C3 1.377(2) . ? C4 C5 1.389(2) . ? C2 C7 1.395(2) . ? C2 C1 1.478(2) . ? C2 C3 1.394(2) . ? C9 C8 1.380(2) . ? C7 C6 1.380(2) . ? C11 C12 1.377(2) . ? C17 C16 1.374(2) . ? C5 C6 1.391(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 N2 C13 119.48(12) . . ? O4 N2 C17 120.25(12) . . ? C17 N2 C13 120.27(12) . . ? N2 C13 C14 120.90(14) . . ? C14 C15 C10 122.00(13) . . ? C14 C15 C16 116.08(13) . . ? C16 C15 C10 121.92(13) . . ? C8 N1 C12 116.07(13) . . ? C9 C10 C15 122.23(13) . . ? C9 C10 C11 116.23(13) . . ? C11 C10 C15 121.54(13) . . ? C3 C4 C5 120.25(14) . . ? C7 C2 C1 122.43(13) . . ? C3 C2 C7 118.65(13) . . ? C3 C2 C1 118.88(13) . . ? C8 C9 C10 119.85(14) . . ? C6 C7 C2 120.72(13) . . ? C12 C11 C10 119.90(14) . . ? C13 C14 C15 121.13(14) . . ? N2 C17 C16 120.10(14) . . ? O1 C1 C2 114.24(13) . . ? O2 C1 O1 122.30(14) . . ? O2 C1 C2 123.45(13) . . ? C17 C16 C15 121.52(14) . . ? C4 C3 C2 120.78(13) . . ? N1 C8 C9 124.00(15) . . ? O3 C5 C4 117.53(13) . . ? O3 C5 C6 122.95(13) . . ? C4 C5 C6 119.52(14) . . ? N1 C12 C11 123.94(15) . . ? C7 C6 C5 120.08(13) . . ? _database_code_depnum_ccdc_archive 'CCDC 974289' ####################################################################### # # 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_BPO-pca _audit_creation_date 2012-10-10 _audit_creation_method ; Olex2 1.2 (compiled 2012.05.09 svn.r2324, GUI svn.r4230) ; _chemical_name_common 'BPO.p-coumaric acid' _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C9 H8 O3, C10 H8 N2 O' _chemical_formula_sum 'C19 H16 N2 O4' _chemical_formula_weight 336.34 _chemical_melting_point ? 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' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/n 1' _space_group_name_Hall '-P 2yn' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.6894(5) _cell_length_b 19.3400(10) _cell_length_c 10.6910(6) _cell_angle_alpha 90.00 _cell_angle_beta 101.843(5) _cell_angle_gamma 90.00 _cell_volume 1556.05(15) _cell_formula_units_Z 4 _cell_measurement_reflns_used 2714 _cell_measurement_temperature 150.0 _cell_measurement_theta_max 29.2813 _cell_measurement_theta_min 2.6999 _exptl_absorpt_coefficient_mu 0.102 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.92300 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.436 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 704 _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.31 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0529 _diffrn_reflns_av_unetI/netI 0.0626 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 8818 _diffrn_reflns_theta_full 24.99 _diffrn_reflns_theta_max 24.99 _diffrn_reflns_theta_min 2.87 _diffrn_ambient_temperature 150.0 _diffrn_detector_area_resol_mean 15.9821 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega 25.00 65.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - 18.9803 -118.0000 134.0000 40 #__ type_ start__ end____ width___ exp.time_ 2 omega -10.00 86.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - 18.9803 77.0000 -120.0000 96 #__ type_ start__ end____ width___ exp.time_ 3 omega -48.00 65.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - 18.9803 0.0000 60.0000 113 #__ type_ start__ end____ width___ exp.time_ 4 omega -7.00 77.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - 18.9803 37.0000 150.0000 84 ; _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0111229000 _diffrn_orient_matrix_UB_12 -0.0362959000 _diffrn_orient_matrix_UB_13 0.0035490000 _diffrn_orient_matrix_UB_21 -0.0273942000 _diffrn_orient_matrix_UB_22 -0.0015059000 _diffrn_orient_matrix_UB_23 -0.0674706000 _diffrn_orient_matrix_UB_31 0.0894464000 _diffrn_orient_matrix_UB_32 -0.0049811000 _diffrn_orient_matrix_UB_33 -0.0054779000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 1818 _reflns_number_total 2725 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; SHELXS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.162 _refine_diff_density_min -0.239 _refine_diff_density_rms 0.048 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 234 _refine_ls_number_reflns 2725 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0841 _refine_ls_R_factor_gt 0.0462 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0396P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0945 _refine_ls_wR_factor_ref 0.1104 _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. DFIX 0.85 0.01 O3 H3 O1 H1 ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.4204(2) 0.43901(9) 0.66699(17) 0.0334(4) Uani 1 1 d D . . O2 O 0.2515(2) 0.41226(8) 0.47613(15) 0.0355(4) Uani 1 1 d . . . O3 O 0.0131(2) 0.82785(9) 0.27516(17) 0.0383(5) Uani 1 1 d D . . N2 N 0.0545(2) 0.75557(10) 0.80162(18) 0.0285(5) Uani 1 1 d . . . O4 O 0.0093(2) 0.81594(8) 0.74674(15) 0.0363(5) Uani 1 1 d . . . N1 N 0.3182(2) 0.43205(9) 1.08315(18) 0.0285(5) Uani 1 1 d . . . C17 C 0.2076(3) 0.56016(11) 0.9709(2) 0.0234(5) Uani 1 1 d . . . C7 C 0.0552(3) 0.76345(12) 0.3219(2) 0.0262(6) Uani 1 1 d . . . C6 C 0.1932(3) 0.75048(12) 0.4252(2) 0.0286(6) Uani 1 1 d . . . H6 H 0.2607 0.7870 0.4659 0.034 Uiso 1 1 calc R . . C10 C 0.0151(3) 0.69708(12) 0.7326(2) 0.0305(6) Uani 1 1 d . . . H10 H -0.0445 0.6999 0.6477 0.037 Uiso 1 1 calc R . . C18 C 0.2183(3) 0.54797(12) 1.1006(2) 0.0280(6) Uani 1 1 d . . . H18 H 0.1891 0.5828 1.1527 0.034 Uiso 1 1 calc R . . C3 C 0.1695(3) 0.55663(11) 0.4463(2) 0.0271(6) Uani 1 1 d . . . H3A H 0.0963 0.5242 0.3971 0.032 Uiso 1 1 calc R . . C8 C -0.0465(3) 0.70883(12) 0.2639(2) 0.0293(6) Uani 1 1 d . . . H8 H -0.1403 0.7169 0.1953 0.035 Uiso 1 1 calc R . . C2 C 0.2933(3) 0.53031(11) 0.5392(2) 0.0286(6) Uani 1 1 d . . . H2 H 0.3662 0.5600 0.5953 0.034 Uiso 1 1 calc R . . C9 C -0.0084(3) 0.64256(12) 0.3080(2) 0.0285(6) Uani 1 1 d . . . H9 H -0.0783 0.6064 0.2683 0.034 Uiso 1 1 calc R . . C13 C 0.1899(3) 0.68897(11) 0.9809(2) 0.0282(6) Uani 1 1 d . . . H13 H 0.2493 0.6872 1.0659 0.034 Uiso 1 1 calc R . . C11 C 0.0617(3) 0.63391(12) 0.7860(2) 0.0290(6) Uani 1 1 d . . . H11 H 0.0328 0.5943 0.7369 0.035 Uiso 1 1 calc R . . C1 C 0.3173(3) 0.45530(12) 0.5550(2) 0.0281(6) Uani 1 1 d . . . C5 C 0.2308(3) 0.68391(12) 0.4676(2) 0.0293(6) Uani 1 1 d . . . H5 H 0.3247 0.6761 0.5363 0.035 Uiso 1 1 calc R . . C16 C 0.2569(3) 0.50584(11) 0.8998(2) 0.0274(6) Uani 1 1 d . . . H16 H 0.2525 0.5112 0.8128 0.033 Uiso 1 1 calc R . . C19 C 0.2721(3) 0.48413(12) 1.1516(2) 0.0296(6) Uani 1 1 d . . . H19 H 0.2766 0.4770 1.2382 0.035 Uiso 1 1 calc R . . C12 C 0.1517(3) 0.62768(12) 0.9124(2) 0.0250(6) Uani 1 1 d . . . C15 C 0.3118(3) 0.44435(12) 0.9594(2) 0.0300(6) Uani 1 1 d . . . H15 H 0.3467 0.4092 0.9105 0.036 Uiso 1 1 calc R . . C14 C 0.1414(3) 0.75197(12) 0.9252(2) 0.0309(6) Uani 1 1 d . . . H14 H 0.1683 0.7923 0.9725 0.037 Uiso 1 1 calc R . . C4 C 0.1310(3) 0.62774(12) 0.4098(2) 0.0256(6) Uani 1 1 d . . . H3 H 0.063(3) 0.8609(10) 0.324(2) 0.074(11) Uiso 1 1 d D . . H1 H 0.435(4) 0.3957(6) 0.682(3) 0.076(11) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0450(11) 0.0215(11) 0.0302(10) -0.0005(9) -0.0007(8) 0.0002(9) O2 0.0486(11) 0.0238(10) 0.0307(10) -0.0057(9) 0.0006(8) -0.0032(8) O3 0.0487(11) 0.0222(11) 0.0373(11) 0.0013(9) -0.0073(8) -0.0007(9) N2 0.0312(12) 0.0196(12) 0.0317(12) 0.0003(10) -0.0006(9) -0.0012(9) O4 0.0478(11) 0.0192(10) 0.0360(11) 0.0060(8) -0.0053(8) 0.0026(8) N1 0.0335(12) 0.0190(11) 0.0308(12) -0.0036(10) 0.0014(9) -0.0024(9) C17 0.0215(12) 0.0186(13) 0.0288(13) -0.0047(11) 0.0021(10) -0.0044(10) C7 0.0303(14) 0.0209(14) 0.0268(13) -0.0010(12) 0.0048(10) 0.0000(11) C6 0.0313(14) 0.0224(14) 0.0286(13) -0.0040(12) -0.0020(10) -0.0050(11) C10 0.0333(14) 0.0256(15) 0.0286(13) -0.0045(12) -0.0029(11) -0.0021(11) C18 0.0321(14) 0.0211(14) 0.0305(13) -0.0052(12) 0.0060(10) 0.0001(11) C3 0.0319(14) 0.0224(14) 0.0272(13) -0.0054(12) 0.0069(10) -0.0054(11) C8 0.0294(14) 0.0270(15) 0.0282(13) -0.0019(12) -0.0017(10) -0.0006(11) C2 0.0380(15) 0.0179(14) 0.0298(13) -0.0034(12) 0.0069(11) -0.0034(11) C9 0.0288(14) 0.0264(15) 0.0291(13) -0.0068(12) 0.0032(11) -0.0063(11) C13 0.0313(14) 0.0229(14) 0.0272(13) 0.0012(12) -0.0014(10) -0.0010(11) C11 0.0348(15) 0.0215(14) 0.0289(13) -0.0044(12) 0.0027(11) -0.0033(11) C1 0.0310(14) 0.0273(15) 0.0265(13) 0.0006(12) 0.0070(11) -0.0024(12) C5 0.0320(14) 0.0259(15) 0.0274(13) 0.0005(12) 0.0004(10) -0.0005(11) C16 0.0329(14) 0.0235(14) 0.0236(13) -0.0033(12) 0.0004(10) -0.0022(11) C19 0.0328(14) 0.0271(14) 0.0278(14) 0.0001(12) 0.0040(11) -0.0046(11) C12 0.0244(13) 0.0224(14) 0.0275(13) -0.0028(12) 0.0033(10) -0.0027(11) C15 0.0347(14) 0.0232(14) 0.0305(14) -0.0081(12) 0.0031(11) -0.0004(11) C14 0.0351(15) 0.0260(15) 0.0268(13) -0.0029(12) -0.0047(10) -0.0019(11) C4 0.0294(13) 0.0205(13) 0.0264(13) -0.0014(12) 0.0049(10) -0.0033(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 O1 C1 1.331(3) . ? O2 C1 1.218(3) . ? O3 C7 1.356(3) . ? N2 O4 1.321(2) . ? N2 C10 1.351(3) . ? N2 C14 1.354(3) . ? N1 C19 1.335(3) . ? N1 C15 1.336(3) . ? C17 C18 1.392(3) . ? C17 C16 1.394(3) . ? C17 C12 1.473(3) . ? C7 C6 1.388(3) . ? C7 C8 1.383(3) . ? C6 C5 1.376(3) . ? C10 C11 1.365(3) . ? C18 C19 1.378(3) . ? C3 C2 1.328(3) . ? C3 C4 1.444(3) . ? C8 C9 1.376(3) . ? C2 C1 1.468(3) . ? C9 C4 1.392(3) . ? C13 C12 1.393(3) . ? C13 C14 1.374(3) . ? C11 C12 1.391(3) . ? C5 C4 1.399(3) . ? C16 C15 1.374(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 N2 C10 119.23(19) . . ? O4 N2 C14 120.7(2) . . ? C10 N2 C14 120.1(2) . . ? C19 N1 C15 116.7(2) . . ? C18 C17 C16 116.6(2) . . ? C18 C17 C12 121.7(2) . . ? C16 C17 C12 121.6(2) . . ? O3 C7 C6 123.0(2) . . ? O3 C7 C8 117.8(2) . . ? C8 C7 C6 119.2(2) . . ? C5 C6 C7 120.4(2) . . ? N2 C10 C11 120.7(2) . . ? C19 C18 C17 119.8(2) . . ? C2 C3 C4 130.0(2) . . ? C9 C8 C7 119.8(2) . . ? C3 C2 C1 121.3(2) . . ? C8 C9 C4 122.4(2) . . ? C14 C13 C12 121.2(2) . . ? C10 C11 C12 121.3(2) . . ? O1 C1 C2 112.0(2) . . ? O2 C1 O1 123.1(2) . . ? O2 C1 C2 124.8(2) . . ? C6 C5 C4 121.4(2) . . ? C15 C16 C17 119.5(2) . . ? N1 C19 C18 123.4(2) . . ? C13 C12 C17 121.3(2) . . ? C11 C12 C17 122.2(2) . . ? C11 C12 C13 116.5(2) . . ? N1 C15 C16 123.9(2) . . ? N2 C14 C13 120.3(2) . . ? C9 C4 C3 119.3(2) . . ? C9 C4 C5 116.8(2) . . ? C5 C4 C3 123.8(2) . . ? _database_code_depnum_ccdc_archive 'CCDC 974290'