# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # 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_35dbna_30c _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H9 N3 O8' _chemical_formula_weight 335.00 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0000 0.0000 '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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 14.061(6) _cell_length_b 5.039(2) _cell_length_c 19.598(8) _cell_angle_alpha 90.00 _cell_angle_beta 102.641(8) _cell_angle_gamma 90.00 _cell_volume 1354.9(10) _cell_formula_units_Z 4 _cell_measurement_temperature 30 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour ? _exptl_crystal_size_max 1.1 _exptl_crystal_size_mid 0.8 _exptl_crystal_size_min 0.5 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.642 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 509 _exptl_absorpt_coefficient_mu 0.000 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 30(.2) _diffrn_radiation_wavelength 'thermal neutron spectrum' _diffrn_radiation_type 'thermal neutrons' _diffrn_radiation_source 'ILL HFR' _diffrn_radiation_monochromator N/A _diffrn_measurement_device_type 'VIVALDI cylindrical image-plate detector' _diffrn_measurement_method Laue _diffrn_detector_area_resol_mean 0.072 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13847 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.8 _diffrn_reflns_theta_max 72.0 _reflns_number_total 3018 _reflns_number_gt 1516 _reflns_threshold_expression >2sigma(I) _computing_data_collection VIVALDI _computing_cell_refinement LAUEGEN _computing_data_reduction 'INTEGRATE+, LAUE4' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3018 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1958 _refine_ls_R_factor_gt 0.0877 _refine_ls_wR_factor_ref 0.1666 _refine_ls_wR_factor_gt 0.1417 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.089 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.4122(3) -0.0708(8) 0.35616(19) 0.0154(8) Uani 1 1 d . . . O2 O 0.4783(3) 0.2521(7) 0.4334(2) 0.0155(9) Uani 1 1 d . . . N1 N 0.21811(18) 0.6370(5) 0.40969(12) 0.0147(5) Uani 1 1 d . . . C1 C 0.4052(2) 0.1358(7) 0.38704(16) 0.0127(7) Uani 1 1 d . . . C2 C 0.3126(3) 0.2907(7) 0.37570(17) 0.0131(7) Uani 1 1 d . . . C3 C 0.2335(3) 0.2219(7) 0.32228(17) 0.0154(7) Uani 1 1 d . . . H1 H 0.2387(6) 0.0543(15) 0.2886(4) 0.0291(16) Uani 1 1 d . . . C4 C 0.1467(3) 0.3655(7) 0.31262(16) 0.0143(7) Uani 1 1 d . . . H2 H 0.0836(6) 0.3185(17) 0.2703(4) 0.0311(17) Uani 1 1 d . . . C5 C 0.1403(2) 0.5726(7) 0.35886(16) 0.0140(6) Uani 1 1 d . . . H3 H 0.0753(6) 0.6921(17) 0.3549(4) 0.0297(16) Uani 1 1 d . . . C6 C 0.3034(3) 0.5051(6) 0.41901(17) 0.0125(7) Uani 1 1 d . . . H4 H 0.3603(6) 0.5755(15) 0.4616(4) 0.0296(16) Uani 1 1 d . . . H9 H 0.5376(6) 0.1336(16) 0.4414(4) 0.0300(16) Uani 1 1 d . . . H8 H 0.2084(5) 0.8047(17) 0.4469(4) 0.0278(15) Uani 1 1 d . . . O3 O 0.3541(3) -0.0241(8) 0.5326(2) 0.0154(8) Uani 1 1 d . . . O4 O 0.1941(3) 0.0125(7) 0.4938(2) 0.0142(8) Uani 1 1 d . . . O5 O 0.5087(3) 0.6036(8) 0.7239(2) 0.0168(8) Uani 1 1 d . . . O6 O 0.4226(3) 0.9306(8) 0.7501(2) 0.0166(8) Uani 1 1 d . . . O7 O 0.0784(3) 0.9809(8) 0.6534(2) 0.0185(9) Uani 1 1 d . . . O8 O 0.0088(3) 0.6907(9) 0.5757(2) 0.0185(8) Uani 1 1 d . . . N2 N 0.0799(2) 0.7800(5) 0.61732(12) 0.0157(5) Uani 1 1 d . . . N3 N 0.4316(2) 0.7217(5) 0.71893(12) 0.0139(5) Uani 1 1 d . . . C7 C 0.2739(2) 0.0767(7) 0.53255(16) 0.0136(6) Uani 1 1 d . . . C8 C 0.2683(2) 0.3059(7) 0.58231(16) 0.0136(6) Uani 1 1 d . . . C9 C 0.1787(3) 0.4295(7) 0.57960(17) 0.0143(7) Uani 1 1 d . . . H5 H 0.1139(6) 0.3574(16) 0.5415(4) 0.0299(17) Uani 1 1 d . . . C10 C 0.1733(2) 0.6433(7) 0.62324(16) 0.0132(7) Uani 1 1 d . . . C11 C 0.2553(3) 0.7381(6) 0.67110(17) 0.0134(7) Uani 1 1 d . . . H6 H 0.2502(6) 0.9054(16) 0.7039(4) 0.0309(17) Uani 1 1 d . . . C12 C 0.3436(2) 0.6129(7) 0.67172(16) 0.0130(7) Uani 1 1 d . . . C13 C 0.3531(3) 0.3980(7) 0.62841(16) 0.0151(7) Uani 1 1 d . . . H7 H 0.4256(6) 0.3070(17) 0.6294(4) 0.0313(17) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.021(2) 0.010(2) 0.0166(16) -0.0005(15) 0.0078(16) 0.0015(15) O2 0.018(2) 0.014(2) 0.0163(18) -0.0029(14) 0.0073(17) -0.0017(13) N1 0.0161(13) 0.0145(14) 0.0135(10) -0.0019(9) 0.0031(9) 0.0017(8) C1 0.0157(18) 0.0113(18) 0.0126(13) 0.0018(12) 0.0065(13) 0.0017(11) C2 0.0137(18) 0.0145(18) 0.0128(13) 0.0035(12) 0.0067(13) 0.0029(12) C3 0.017(2) 0.016(2) 0.0138(14) -0.0011(12) 0.0043(14) -0.0009(12) H1 0.043(5) 0.016(4) 0.030(3) -0.009(3) 0.012(3) 0.008(3) C4 0.0173(18) 0.0133(19) 0.0129(13) -0.0038(12) 0.0048(13) -0.0004(12) H2 0.032(5) 0.031(4) 0.024(3) -0.003(3) -0.009(3) -0.001(3) C5 0.0170(18) 0.0128(18) 0.0135(14) -0.0016(13) 0.0066(13) 0.0026(13) H3 0.020(4) 0.031(4) 0.039(4) 0.002(3) 0.008(3) 0.006(3) C6 0.0098(19) 0.0161(19) 0.0107(14) -0.0032(12) 0.0003(13) -0.0003(11) H4 0.031(4) 0.025(4) 0.027(3) -0.011(3) -0.007(3) -0.005(3) H9 0.030(4) 0.026(4) 0.032(4) -0.005(3) 0.001(3) 0.002(3) H8 0.025(4) 0.038(4) 0.020(3) -0.006(3) 0.006(3) 0.000(3) O3 0.014(2) 0.016(2) 0.0163(16) -0.0042(14) 0.0043(15) 0.0030(13) O4 0.013(2) 0.013(2) 0.0162(17) -0.0002(13) 0.0032(16) 0.0048(12) O5 0.0147(19) 0.017(2) 0.0178(16) 0.0007(16) 0.0019(15) 0.0000(14) O6 0.020(2) 0.014(2) 0.0164(17) -0.0007(16) 0.0040(15) -0.0014(15) O7 0.020(2) 0.020(2) 0.0174(18) -0.0007(15) 0.0087(17) 0.0035(14) O8 0.012(2) 0.021(2) 0.0217(18) -0.0071(17) 0.0021(16) -0.0007(16) N2 0.0167(14) 0.0169(14) 0.0143(11) -0.0006(9) 0.0052(10) 0.0023(9) N3 0.0171(14) 0.0136(13) 0.0117(9) -0.0002(9) 0.0047(9) 0.0002(8) C7 0.0153(17) 0.0131(18) 0.0136(14) -0.0004(13) 0.0059(13) 0.0009(12) C8 0.0140(18) 0.0139(17) 0.0137(14) -0.0026(13) 0.0047(13) 0.0009(12) C9 0.0128(17) 0.0122(18) 0.0178(15) 0.0014(14) 0.0032(13) 0.0007(13) H5 0.034(4) 0.033(5) 0.024(3) -0.007(3) 0.007(3) -0.006(3) C10 0.0172(18) 0.0090(18) 0.0144(13) -0.0009(12) 0.0057(13) -0.0003(11) C11 0.014(2) 0.014(2) 0.0125(13) -0.0007(12) 0.0025(13) 0.0003(11) H6 0.045(5) 0.020(4) 0.027(3) -0.012(3) 0.008(3) 0.002(3) C12 0.0108(17) 0.0161(19) 0.0129(13) -0.0003(12) 0.0042(12) 0.0009(11) C13 0.0185(18) 0.0146(18) 0.0137(13) -0.0001(13) 0.0069(13) 0.0005(13) H7 0.022(4) 0.032(4) 0.038(4) -0.001(3) 0.005(3) 0.012(3) _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 1.219(5) . ? O2 C1 1.348(5) . ? O2 H9 1.010(10) . ? N1 C6 1.348(4) . ? N1 C5 1.348(4) . ? N1 H8 1.144(8) . ? C1 C2 1.492(5) . ? C2 C3 1.395(5) . ? C2 C6 1.397(5) . ? C3 C4 1.395(5) . ? C3 H1 1.085(8) . ? C4 C5 1.398(5) . ? C4 H2 1.099(8) . ? C5 H3 1.083(8) . ? C6 H4 1.082(7) . ? O3 C7 1.238(5) . ? O4 C7 1.251(6) . ? O5 N3 1.221(5) . ? O6 N3 1.237(4) . ? O7 N2 1.238(5) . ? O8 N2 1.228(5) . ? N2 C10 1.466(4) . ? N3 C12 1.480(4) . ? C7 C8 1.524(5) . ? C8 C9 1.397(5) . ? C8 C13 1.407(5) . ? C9 C10 1.388(5) . ? C9 H5 1.105(8) . ? C10 C11 1.402(5) . ? C11 C12 1.389(5) . ? C11 H6 1.072(8) . ? C12 C13 1.400(5) . ? C13 H7 1.115(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 C1 O2 H9 109.3(5) . . ? C6 N1 C5 122.4(3) . . ? C6 N1 H8 120.3(4) . . ? C5 N1 H8 117.3(4) . . ? O1 C1 O2 125.0(4) . . ? O1 C1 C2 122.4(3) . . ? O2 C1 C2 112.6(3) . . ? C3 C2 C6 118.9(3) . . ? C3 C2 C1 120.6(3) . . ? C6 C2 C1 120.5(3) . . ? C2 C3 C4 120.2(3) . . ? C2 C3 H1 120.1(5) . . ? C4 C3 H1 119.7(5) . . ? C3 C4 C5 118.5(3) . . ? C3 C4 H2 121.9(5) . . ? C5 C4 H2 119.6(5) . . ? N1 C5 C4 120.1(3) . . ? N1 C5 H3 117.0(5) . . ? C4 C5 H3 122.8(5) . . ? N1 C6 C2 119.8(3) . . ? N1 C6 H4 115.4(5) . . ? C2 C6 H4 124.8(5) . . ? O8 N2 O7 124.4(4) . . ? O8 N2 C10 117.7(3) . . ? O7 N2 C10 117.8(3) . . ? O5 N3 O6 124.1(4) . . ? O5 N3 C12 118.4(3) . . ? O6 N3 C12 117.5(3) . . ? O3 C7 O4 126.2(4) . . ? O3 C7 C8 119.0(3) . . ? O4 C7 C8 114.8(3) . . ? C9 C8 C13 120.5(3) . . ? C9 C8 C7 119.0(3) . . ? C13 C8 C7 120.4(3) . . ? C10 C9 C8 119.5(3) . . ? C10 C9 H5 121.6(5) . . ? C8 C9 H5 118.8(5) . . ? C9 C10 C11 122.0(3) . . ? C9 C10 N2 119.0(3) . . ? C11 C10 N2 119.0(3) . . ? C12 C11 C10 117.0(3) . . ? C12 C11 H6 121.9(6) . . ? C10 C11 H6 121.1(5) . . ? C11 C12 C13 123.3(3) . . ? C11 C12 N3 117.4(3) . . ? C13 C12 N3 119.2(3) . . ? C12 C13 C8 117.7(3) . . ? C12 C13 H7 121.1(5) . . ? C8 C13 H7 121.2(5) . . ? _diffrn_measured_fraction_theta_max 0.730 _diffrn_reflns_theta_full 30.51 _diffrn_measured_fraction_theta_full 0.730 _refine_diff_density_max 1.289 _refine_diff_density_min -1.342 _refine_diff_density_rms 0.312 _database_code_depnum_ccdc_archive 'CCDC 939942' ####################################################################### # # 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_35dbna_300c _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H9 N3 O8' _chemical_formula_weight 335.00 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0000 0.0000 '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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 14.061(6) _cell_length_b 5.039(2) _cell_length_c 19.598(8) _cell_angle_alpha 90.00 _cell_angle_beta 102.641(8) _cell_angle_gamma 90.00 _cell_volume 1354.9(10) _cell_formula_units_Z 4 _cell_measurement_temperature 300 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour ? _exptl_crystal_size_max 1.1 _exptl_crystal_size_mid 0.8 _exptl_crystal_size_min 0.5 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.642 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 509 _exptl_absorpt_coefficient_mu 0.000 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 300(2) _diffrn_radiation_wavelength 'thermal neutron spectrum' _diffrn_radiation_type 'thermal neutrons' _diffrn_radiation_source 'ILL HFR' _diffrn_radiation_monochromator N/A _diffrn_measurement_device_type 'VIVALDI cylindrical image-plate detector' _diffrn_measurement_method Laue _diffrn_detector_area_resol_mean 0.072 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10371 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.8 _diffrn_reflns_theta_max 72 _reflns_number_total 2171 _reflns_number_gt 836 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2171 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2548 _refine_ls_R_factor_gt 0.0823 _refine_ls_wR_factor_ref 0.1566 _refine_ls_wR_factor_gt 0.1166 _refine_ls_goodness_of_fit_ref 0.964 _refine_ls_restrained_S_all 0.964 _refine_ls_shift/su_max 0.021 _refine_ls_shift/su_mean 0.004 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 0.4118(6) -0.0489(13) 0.3553(4) 0.067(2) Uani 1 1 d . . . O2 O 0.4787(5) 0.2529(14) 0.4345(4) 0.0590(19) Uani 1 1 d . . . N1 N 0.2214(3) 0.6461(8) 0.41169(19) 0.0463(9) Uani 1 1 d . . . C1 C 0.4050(4) 0.1491(12) 0.3866(3) 0.0493(13) Uani 1 1 d . . . C2 C 0.3131(4) 0.3081(10) 0.3762(2) 0.0428(12) Uani 1 1 d . . . C3 C 0.2345(4) 0.2473(10) 0.3234(3) 0.0502(15) Uani 1 1 d . . . H1 H 0.2395(10) 0.083(2) 0.2889(7) 0.083(4) Uani 1 1 d . . . C4 C 0.1478(4) 0.3923(11) 0.3138(3) 0.0564(15) Uani 1 1 d . . . H2 H 0.0886(9) 0.349(2) 0.2723(6) 0.079(3) Uani 1 1 d . . . C5 C 0.1439(4) 0.5902(11) 0.3603(3) 0.0464(13) Uani 1 1 d . . . H3 H 0.0808(9) 0.708(3) 0.3565(6) 0.076(3) Uani 1 1 d . . . C6 C 0.3056(4) 0.5117(9) 0.4204(3) 0.0424(13) Uani 1 1 d . . . H4 H 0.3633(9) 0.569(2) 0.4622(6) 0.072(3) Uani 1 1 d . . . H9 H 0.5367(9) 0.147(2) 0.4411(6) 0.068(3) Uani 1 1 d . . . H8 H 0.2125(8) 0.810(2) 0.4482(6) 0.067(3) Uani 1 1 d . . . O3 O 0.3545(5) -0.0255(13) 0.5364(4) 0.0619(19) Uani 1 1 d . . . O4 O 0.1970(5) 0.0102(11) 0.4928(4) 0.0568(18) Uani 1 1 d . . . O5 O 0.5054(5) 0.5804(14) 0.7266(4) 0.0656(18) Uani 1 1 d . . . O6 O 0.4205(5) 0.9020(14) 0.7507(4) 0.069(2) Uani 1 1 d . . . O7 O 0.0745(6) 0.9535(16) 0.6510(5) 0.082(2) Uani 1 1 d . . . O8 O 0.0102(5) 0.6736(17) 0.5750(5) 0.084(2) Uani 1 1 d . . . N2 N 0.0802(3) 0.7620(8) 0.6158(2) 0.0589(12) Uani 1 1 d . . . N3 N 0.4303(3) 0.6991(8) 0.72001(18) 0.0504(10) Uani 1 1 d . . . C7 C 0.2761(4) 0.0776(9) 0.5342(3) 0.0443(12) Uani 1 1 d . . . C8 C 0.2691(4) 0.2988(9) 0.5823(2) 0.0427(12) Uani 1 1 d . . . C9 C 0.1794(4) 0.4203(10) 0.5779(3) 0.0438(12) Uani 1 1 d . . . H5 H 0.1171(8) 0.353(2) 0.5407(5) 0.061(3) Uani 1 1 d . . . C10 C 0.1737(3) 0.6286(10) 0.6217(3) 0.0472(13) Uani 1 1 d . . . C11 C 0.2535(4) 0.7199(11) 0.6695(3) 0.0503(14) Uani 1 1 d . . . H6 H 0.2482(8) 0.882(2) 0.7022(6) 0.066(3) Uani 1 1 d . . . C12 C 0.3416(4) 0.5997(10) 0.6720(2) 0.0418(12) Uani 1 1 d . . . C13 C 0.3524(4) 0.3883(10) 0.6296(3) 0.0439(12) Uani 1 1 d . . . H7 H 0.4218(8) 0.2925(19) 0.6319(5) 0.056(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.079(6) 0.055(4) 0.068(4) -0.005(4) 0.017(4) 0.022(3) O2 0.046(5) 0.068(5) 0.061(4) -0.015(3) 0.006(4) 0.008(3) N1 0.048(2) 0.040(2) 0.048(2) -0.0006(18) 0.0041(19) 0.0034(17) C1 0.045(3) 0.056(3) 0.048(3) 0.008(3) 0.014(3) 0.004(3) C2 0.052(3) 0.035(3) 0.041(2) -0.001(2) 0.010(2) 0.000(2) C3 0.052(4) 0.053(4) 0.041(3) -0.008(2) 0.000(3) -0.003(2) H1 0.104(10) 0.057(7) 0.078(8) -0.024(7) 0.001(7) 0.012(6) C4 0.046(3) 0.061(4) 0.055(3) -0.010(3) -0.005(3) 0.010(3) H2 0.076(8) 0.079(8) 0.069(7) -0.029(6) -0.012(7) 0.002(7) C5 0.045(4) 0.045(3) 0.047(3) -0.004(3) 0.003(3) 0.003(2) H3 0.058(8) 0.092(9) 0.072(7) -0.004(6) 0.000(6) 0.024(7) C6 0.044(3) 0.040(3) 0.041(3) -0.005(2) 0.005(3) 0.001(2) H4 0.057(7) 0.078(8) 0.073(8) -0.023(6) -0.005(6) 0.015(6) H9 0.064(8) 0.077(8) 0.062(7) 0.001(6) 0.015(6) 0.024(7) H8 0.068(7) 0.073(8) 0.057(6) 0.003(6) 0.008(6) 0.011(6) O3 0.043(4) 0.072(4) 0.064(4) -0.017(3) -0.003(4) 0.018(3) O4 0.052(4) 0.048(4) 0.063(4) -0.020(3) -0.003(4) 0.007(3) O5 0.044(4) 0.066(4) 0.079(5) -0.005(4) -0.004(4) 0.002(3) O6 0.064(5) 0.065(4) 0.066(4) -0.017(4) -0.010(4) -0.003(4) O7 0.072(5) 0.086(5) 0.089(6) -0.035(4) 0.020(5) 0.021(4) O8 0.056(5) 0.096(6) 0.099(5) -0.023(5) 0.013(5) 0.027(4) N2 0.049(3) 0.062(3) 0.066(3) -0.007(2) 0.012(2) 0.0072(18) N3 0.057(3) 0.048(2) 0.0409(19) -0.0015(18) 0.0009(19) -0.013(2) C7 0.040(3) 0.046(3) 0.048(3) -0.001(2) 0.011(3) 0.000(2) C8 0.048(3) 0.039(3) 0.041(3) 0.001(2) 0.010(2) 0.001(2) C9 0.036(3) 0.044(3) 0.052(3) -0.003(3) 0.008(3) 0.004(2) H5 0.055(6) 0.057(6) 0.063(6) -0.016(5) -0.003(5) -0.003(5) C10 0.041(3) 0.049(3) 0.051(3) -0.004(3) 0.009(3) 0.001(2) C11 0.054(4) 0.050(3) 0.048(3) 0.000(3) 0.013(3) -0.005(3) H6 0.070(7) 0.063(8) 0.065(6) -0.024(6) 0.015(6) -0.001(5) C12 0.048(3) 0.040(3) 0.037(2) 0.005(2) 0.007(2) -0.004(2) C13 0.039(3) 0.044(3) 0.044(3) 0.004(2) -0.001(3) -0.003(2) H7 0.048(7) 0.046(6) 0.071(7) 0.006(5) 0.007(5) 0.007(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.186(8) . ? O2 C1 1.342(8) . ? O2 H9 0.960(17) . ? N1 C5 1.342(6) . ? N1 C6 1.342(6) . ? N1 H8 1.119(15) . ? C1 C2 1.497(7) . ? C2 C6 1.362(7) . ? C2 C3 1.373(7) . ? C3 C4 1.398(7) . ? C3 H1 1.081(16) . ? C4 C5 1.361(8) . ? C4 H2 1.050(14) . ? C5 H3 1.057(15) . ? C6 H4 1.059(15) . ? O3 C7 1.212(7) . ? O4 C7 1.270(8) . ? O5 N3 1.195(7) . ? O6 N3 1.209(7) . ? O7 N2 1.199(7) . ? O8 N2 1.209(8) . ? N2 C10 1.459(6) . ? N3 C12 1.476(6) . ? C7 C8 1.477(7) . ? C8 C9 1.387(7) . ? C8 C13 1.400(7) . ? C9 C10 1.370(7) . ? C9 H5 1.065(14) . ? C10 C11 1.373(7) . ? C11 C12 1.371(7) . ? C11 H6 1.050(15) . ? C12 C13 1.379(7) . ? C13 H7 1.081(13) . ? 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 O2 H9 112.3(8) . . ? C5 N1 C6 122.6(5) . . ? C5 N1 H8 116.7(6) . . ? C6 N1 H8 120.7(6) . . ? O1 C1 O2 123.5(6) . . ? O1 C1 C2 123.0(6) . . ? O2 C1 C2 113.5(6) . . ? C6 C2 C3 119.1(5) . . ? C6 C2 C1 120.1(5) . . ? C3 C2 C1 120.8(5) . . ? C2 C3 C4 121.3(5) . . ? C2 C3 H1 119.3(9) . . ? C4 C3 H1 119.4(9) . . ? C5 C4 C3 117.1(5) . . ? C5 C4 H2 121.8(8) . . ? C3 C4 H2 121.2(8) . . ? N1 C5 C4 120.7(5) . . ? N1 C5 H3 117.8(8) . . ? C4 C5 H3 121.5(8) . . ? N1 C6 C2 119.2(5) . . ? N1 C6 H4 117.8(7) . . ? C2 C6 H4 123.0(7) . . ? O7 N2 O8 122.0(6) . . ? O7 N2 C10 119.8(6) . . ? O8 N2 C10 118.2(5) . . ? O5 N3 O6 124.3(6) . . ? O5 N3 C12 120.1(5) . . ? O6 N3 C12 115.5(5) . . ? O3 C7 O4 124.8(6) . . ? O3 C7 C8 119.2(5) . . ? O4 C7 C8 116.0(5) . . ? C9 C8 C13 121.2(5) . . ? C9 C8 C7 118.6(5) . . ? C13 C8 C7 120.2(5) . . ? C10 C9 C8 118.4(5) . . ? C10 C9 H5 121.5(7) . . ? C8 C9 H5 120.1(7) . . ? C9 C10 C11 122.3(5) . . ? C9 C10 N2 118.6(5) . . ? C11 C10 N2 119.2(5) . . ? C12 C11 C10 118.2(5) . . ? C12 C11 H6 120.4(8) . . ? C10 C11 H6 121.4(8) . . ? C11 C12 C13 122.5(5) . . ? C11 C12 N3 120.3(5) . . ? C13 C12 N3 117.2(5) . . ? C12 C13 C8 117.4(5) . . ? C12 C13 H7 122.5(7) . . ? C8 C13 H7 120.0(7) . . ? _diffrn_measured_fraction_theta_max 0.730 _diffrn_reflns_theta_full 27.02 _diffrn_measured_fraction_theta_full 0.730 _refine_diff_density_max 0.588 _refine_diff_density_min -0.540 _refine_diff_density_rms 0.133 _database_code_depnum_ccdc_archive 'CCDC 939943'