# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 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_1 #TrackingRef 'web_deposit_cif_file_0_MattiHaukka_1336452577.Kopylovich.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H9 N3 O4' _chemical_formula_sum 'C8 H9 N3 O4' _chemical_formula_weight 211.18 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.765(7) _cell_length_b 4.612(3) _cell_length_c 17.297(11) _cell_angle_alpha 90.00 _cell_angle_beta 97.133(13) _cell_angle_gamma 90.00 _cell_volume 852.1(10) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 719 _cell_measurement_theta_min 2.85 _cell_measurement_theta_max 24.78 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.646 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 0.134 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9409 _exptl_absorpt_correction_T_max 0.9954 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_measurement_device_type 'Bruker KAPPA APEX II CCD' _diffrn_measurement_device '62mm x 62mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 16 _diffrn_measurement_method '\f scans and \w scans with \k offset' _diffrn_reflns_number 4187 _diffrn_reflns_av_R_equivalents 0.0603 _diffrn_reflns_av_sigmaI/netI 0.0765 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 25.25 _reflns_number_total 1496 _reflns_number_gt 905 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2010)' _computing_cell_refinement 'SAINT (Bruker AXS, 2009)' _computing_data_reduction 'SAINT (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Diamond v.3.2g (Brandenburg, 2011)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0642P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1496 _refine_ls_number_parameters 138 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1068 _refine_ls_R_factor_gt 0.0529 _refine_ls_wR_factor_ref 0.1370 _refine_ls_wR_factor_gt 0.1148 _refine_ls_goodness_of_fit_ref 0.998 _refine_ls_restrained_S_all 0.998 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.2873(2) -0.5676(5) 0.83190(12) 0.0281(6) Uani 1 1 d . . . O2 O -0.0265(2) 0.0946(5) 0.82452(12) 0.0237(6) Uani 1 1 d . . . O3 O 0.4467(2) -0.2705(5) 1.04807(12) 0.0275(6) Uani 1 1 d . . . O4 O 0.1094(2) 0.3894(5) 1.04568(12) 0.0252(6) Uani 1 1 d . . . N1 N 0.2811(2) -0.2612(6) 0.93393(14) 0.0202(6) Uani 1 1 d . . . H1 H 0.3516 -0.3238 0.9591 0.030 Uiso 1 1 d R . . N2 N 0.1272(2) -0.2445(6) 0.82800(14) 0.0219(7) Uani 1 1 d . . . H2 H 0.0968 -0.3197 0.7842 0.033 Uiso 1 1 d R . . N3 N 0.1186(2) 0.0647(6) 0.93182(13) 0.0200(7) Uani 1 1 d . . . H3 H 0.0858 0.2008 0.9564 0.030 Uiso 1 1 d R . . C1 C 0.2356(3) -0.3722(7) 0.86254(17) 0.0208(8) Uani 1 1 d . . . C2 C 0.0665(3) -0.0219(8) 0.85914(18) 0.0210(8) Uani 1 1 d . . . C3 C 0.2258(3) -0.0451(7) 0.97064(17) 0.0191(7) Uani 1 1 d . . . C4 C 0.2776(3) 0.0596(7) 1.04473(17) 0.0186(7) Uani 1 1 d . . . C5 C 0.3958(3) -0.0643(7) 1.07981(17) 0.0214(8) Uani 1 1 d . . . C6 C 0.4676(3) 0.0399(8) 1.15475(18) 0.0294(9) Uani 1 1 d . . . H6A H 0.5441 -0.0753 1.1664 0.044 Uiso 1 1 calc R . . H6B H 0.4157 0.0185 1.1971 0.044 Uiso 1 1 calc R . . H6C H 0.4897 0.2445 1.1495 0.044 Uiso 1 1 calc R . . C7 C 0.2076(3) 0.2849(7) 1.08046(17) 0.0205(7) Uani 1 1 d . . . C8 C 0.2442(3) 0.4000(8) 1.16133(17) 0.0266(8) Uani 1 1 d . . . H8A H 0.2411 0.2428 1.1992 0.040 Uiso 1 1 calc R . . H8B H 0.1860 0.5540 1.1721 0.040 Uiso 1 1 calc R . . H8C H 0.3294 0.4782 1.1655 0.040 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0305(14) 0.0305(15) 0.0226(13) -0.0056(11) 0.0002(10) 0.0072(11) O2 0.0276(13) 0.0257(14) 0.0169(12) -0.0002(10) -0.0006(10) 0.0058(11) O3 0.0303(13) 0.0300(16) 0.0213(13) -0.0034(11) -0.0005(10) 0.0067(11) O4 0.0288(13) 0.0274(15) 0.0190(12) -0.0025(10) 0.0013(10) 0.0057(11) N1 0.0236(15) 0.0238(17) 0.0127(14) -0.0034(12) 0.0008(11) 0.0039(12) N2 0.0269(15) 0.0236(17) 0.0144(14) -0.0023(12) -0.0005(11) 0.0010(13) N3 0.0246(15) 0.0229(18) 0.0131(14) -0.0034(12) 0.0041(11) 0.0020(12) C1 0.0281(19) 0.019(2) 0.0159(17) 0.0020(14) 0.0041(14) -0.0005(15) C2 0.0259(18) 0.023(2) 0.0153(17) -0.0023(14) 0.0064(14) -0.0029(15) C3 0.0239(18) 0.0178(19) 0.0166(17) 0.0041(14) 0.0067(14) -0.0022(14) C4 0.0248(17) 0.0176(19) 0.0133(16) -0.0025(13) 0.0019(13) -0.0024(14) C5 0.0294(19) 0.020(2) 0.0155(17) 0.0005(14) 0.0046(14) -0.0029(15) C6 0.0263(19) 0.037(2) 0.024(2) -0.0032(16) -0.0008(14) 0.0046(16) C7 0.0240(18) 0.022(2) 0.0160(17) 0.0014(14) 0.0052(14) -0.0053(15) C8 0.033(2) 0.030(2) 0.0165(17) -0.0034(15) 0.0010(14) 0.0079(16) _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 1.215(4) . ? O2 C2 1.225(4) . ? O3 C5 1.257(4) . yes O4 C7 1.246(4) . yes N1 C3 1.358(4) . ? N1 C1 1.370(4) . ? N1 H1 0.8754 . ? N2 C2 1.363(4) . ? N2 C1 1.376(4) . ? N2 H2 0.8598 . ? N3 C3 1.359(4) . ? N3 C2 1.371(4) . ? N3 H3 0.8579 . ? C3 C4 1.418(4) . yes C4 C5 1.457(4) . yes C4 C7 1.465(4) . yes C5 C6 1.503(4) . yes C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C8 1.502(4) . yes C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? 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 C3 N1 C1 124.5(3) . . ? C3 N1 H1 114.4 . . ? C1 N1 H1 121.0 . . ? C2 N2 C1 125.0(3) . . ? C2 N2 H2 120.2 . . ? C1 N2 H2 114.8 . . ? C3 N3 C2 124.8(3) . . ? C3 N3 H3 113.8 . . ? C2 N3 H3 121.4 . . ? O1 C1 N1 122.6(3) . . ? O1 C1 N2 122.5(3) . . ? N1 C1 N2 114.9(3) . . ? O2 C2 N2 122.7(3) . . ? O2 C2 N3 122.5(3) . . ? N2 C2 N3 114.8(3) . . ? N1 C3 N3 115.9(3) . . ? N1 C3 C4 121.8(3) . . ? N3 C3 C4 122.3(3) . . ? C3 C4 C5 117.9(3) . . ? C3 C4 C7 117.3(3) . . ? C5 C4 C7 124.8(3) . . yes O3 C5 C4 121.3(3) . . ? O3 C5 C6 114.4(3) . . ? C4 C5 C6 124.2(3) . . yes C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? O4 C7 C4 121.4(3) . . ? O4 C7 C8 114.9(3) . . ? C4 C7 C8 123.7(3) . . yes C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag N1 H1 O3 0.88 1.76 2.490(3) 139.8 . yes N2 H2 O2 0.86 1.98 2.824(4) 167.6 2_546 yes N3 H3 O4 0.86 1.76 2.486(3) 140.5 . yes _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 25.25 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.214 _refine_diff_density_min -0.343 _refine_diff_density_rms 0.065 _database_code_depnum_ccdc_archive 'CCDC 880876' ####################################################################### # # 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_5 #TrackingRef 'web_deposit_cif_file_0_MattiHaukka_1336452577.Kopylovich.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H7 N3 O3' _chemical_formula_sum 'C6 H7 N3 O3' _chemical_formula_weight 169.15 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.0878(6) _cell_length_b 11.2798(8) _cell_length_c 6.7696(5) _cell_angle_alpha 90.00 _cell_angle_beta 92.969(3) _cell_angle_gamma 90.00 _cell_volume 693.01(8) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3113 _cell_measurement_theta_min 2.88 _cell_measurement_theta_max 32.74 _exptl_crystal_description block _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.621 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 352 _exptl_absorpt_coefficient_mu 0.133 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9707 _exptl_absorpt_correction_T_max 0.9891 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_measurement_device_type 'Bruker KAPPA APEX II CCD' _diffrn_measurement_device '62mm x 62mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 16 _diffrn_measurement_method '\f scans and \w scans with \k offset' _diffrn_reflns_number 7656 _diffrn_reflns_av_R_equivalents 0.0284 _diffrn_reflns_av_sigmaI/netI 0.0244 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 28.00 _reflns_number_total 1667 _reflns_number_gt 1376 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2010)' _computing_cell_refinement 'SAINT (Bruker AXS, 2009)' _computing_data_reduction 'SAINT (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Diamond v.3.2g (Brandenburg, 2011)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0568P)^2^+0.1814P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1667 _refine_ls_number_parameters 122 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0470 _refine_ls_R_factor_gt 0.0362 _refine_ls_wR_factor_ref 0.1009 _refine_ls_wR_factor_gt 0.0943 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.84205(10) -0.07321(8) 0.08753(15) 0.0197(2) Uani 1 1 d . . . O2 O 0.91239(10) 0.32463(8) 0.03806(15) 0.0215(2) Uani 1 1 d . . . O3 O 0.41134(10) -0.02192(7) 0.28734(14) 0.0182(2) Uani 1 1 d . . . N1 N 0.66469(12) 0.05334(9) 0.17698(17) 0.0149(2) Uani 1 1 d . . . N2 N 0.88041(11) 0.12540(9) 0.05783(16) 0.0157(2) Uani 1 1 d . . . N3 N 0.69928(11) 0.25547(10) 0.15406(16) 0.0143(2) Uani 1 1 d . . . C1 C 0.79991(13) 0.02838(11) 0.10650(19) 0.0149(3) Uani 1 1 d . . . C2 C 0.83713(14) 0.24158(11) 0.08098(19) 0.0154(3) Uani 1 1 d . . . C3 C 0.60840(13) 0.16399(10) 0.19785(18) 0.0134(3) Uani 1 1 d . . . C4 C 0.46921(13) 0.18059(10) 0.26140(19) 0.0148(3) Uani 1 1 d . . . H4 H 0.4343 0.2594 0.2752 0.018 Uiso 1 1 calc R . . C5 C 0.37424(13) 0.08493(11) 0.30776(18) 0.0148(3) Uani 1 1 d . . . C6 C 0.22670(14) 0.11440(11) 0.3840(2) 0.0188(3) Uani 1 1 d . . . H6A H 0.1630 0.0443 0.3741 0.028 Uiso 1 1 calc R . . H6B H 0.1816 0.1790 0.3052 0.028 Uiso 1 1 calc R . . H6C H 0.2390 0.1392 0.5227 0.028 Uiso 1 1 calc R . . H1 H 0.604(2) -0.0084(18) 0.206(3) 0.037(5) Uiso 1 1 d . . . H3 H 0.669(2) 0.3309(15) 0.162(3) 0.025(4) Uiso 1 1 d . . . H2 H 0.970(2) 0.1104(15) 0.009(3) 0.031(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0161(5) 0.0137(5) 0.0300(6) 0.0000(4) 0.0089(4) 0.0026(3) O2 0.0164(5) 0.0168(5) 0.0322(6) -0.0001(4) 0.0097(4) -0.0027(3) O3 0.0154(4) 0.0130(4) 0.0268(5) -0.0001(4) 0.0064(4) -0.0010(3) N1 0.0115(5) 0.0118(5) 0.0219(6) -0.0001(4) 0.0057(4) 0.0000(4) N2 0.0110(5) 0.0157(5) 0.0210(6) -0.0002(4) 0.0066(4) 0.0007(4) N3 0.0108(5) 0.0120(5) 0.0206(6) 0.0005(4) 0.0051(4) 0.0018(4) C1 0.0128(6) 0.0154(6) 0.0168(6) -0.0002(5) 0.0035(4) 0.0015(4) C2 0.0129(6) 0.0168(6) 0.0168(6) -0.0003(5) 0.0031(4) 0.0008(5) C3 0.0128(6) 0.0126(6) 0.0148(6) 0.0001(4) 0.0009(4) 0.0001(4) C4 0.0123(6) 0.0128(6) 0.0196(6) -0.0003(5) 0.0038(5) 0.0014(4) C5 0.0115(6) 0.0171(6) 0.0159(6) -0.0003(5) 0.0023(5) -0.0001(4) C6 0.0130(6) 0.0175(6) 0.0264(7) -0.0001(5) 0.0072(5) 0.0005(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 1.2172(15) . ? O2 C2 1.2043(15) . ? O3 C5 1.2610(15) . yes N1 C3 1.3590(15) . ? N1 C1 1.3703(15) . ? N1 H1 0.91(2) . ? N2 C1 1.3661(15) . ? N2 C2 1.3795(16) . ? N2 H2 0.910(19) . ? N3 C3 1.3639(15) . ? N3 C2 1.3795(16) . ? N3 H3 0.897(17) . ? C3 C4 1.3698(17) . yes C4 C5 1.4268(17) . yes C4 H4 0.9500 . ? C5 C6 1.4989(17) . yes C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? 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 C3 N1 C1 125.03(11) . . ? C3 N1 H1 116.4(12) . . ? C1 N1 H1 118.4(12) . . ? C1 N2 C2 125.04(10) . . ? C1 N2 H2 116.1(11) . . ? C2 N2 H2 118.9(11) . . ? C3 N3 C2 124.30(11) . . ? C3 N3 H3 120.8(11) . . ? C2 N3 H3 114.7(11) . . ? O1 C1 N2 123.60(11) . . ? O1 C1 N1 121.53(11) . . ? N2 C1 N1 114.87(10) . . ? O2 C2 N3 122.40(11) . . ? O2 C2 N2 122.87(11) . . ? N3 C2 N2 114.72(11) . . ? N1 C3 N3 115.90(11) . . ? N1 C3 C4 121.12(11) . . ? N3 C3 C4 122.97(10) . . ? C3 C4 C5 123.00(11) . . ? C3 C4 H4 118.5 . . ? C5 C4 H4 118.5 . . ? O3 C5 C4 122.04(11) . . yes O3 C5 C6 119.92(11) . . yes C4 C5 C6 118.04(11) . . yes C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag N1 H1 O3 0.91(2) 1.873(19) 2.5996(14) 134.9(17) . yes N3 H3 O3 0.897(17) 1.852(18) 2.7412(14) 170.5(17) 2_655 yes N2 H2 O1 0.910(19) 1.907(19) 2.8167(14) 177.6(16) 3_755 yes _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.341 _refine_diff_density_min -0.226 _refine_diff_density_rms 0.051 _database_code_depnum_ccdc_archive 'CCDC 880877'