# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Artur Stefankiewicz' _publ_contact_author_email arturstefankiewicz@gmail.com loop_ _publ_author_name 'Artur Stefankiewicz' 'Jack Harrowfield' data_shelxl _database_code_depnum_ccdc_archive 'CCDC 838207' #TrackingRef 'web_deposit_cif_file_0_JackHarrowfield_1312558687.ArturMars.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H26 N6 O2 S2' _chemical_formula_weight 470.61 _chemical_absolute_configuration ? 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall ? 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 8.0960(2) _cell_length_b 9.8380(2) _cell_length_c 15.2620(5) _cell_angle_alpha 90.00 _cell_angle_beta 103.0690(9) _cell_angle_gamma 90.00 _cell_volume 1184.11(5) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3213 _cell_measurement_theta_min 1.358 _cell_measurement_theta_max 30.034 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.320 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.256 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method '\p scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5856 _diffrn_reflns_av_R_equivalents 0.0177 _diffrn_reflns_av_sigmaI/netI 0.0385 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.31 _diffrn_reflns_theta_max 30.01 _reflns_number_total 3443 _reflns_number_gt 2720 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo (Nonius B.V., 1998)' _computing_data_reduction 'Denzo (Nonius B.V., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON 98 (Spek, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0600P)^2^+0.5377P] 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 3443 _refine_ls_number_parameters 146 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0634 _refine_ls_R_factor_gt 0.0473 _refine_ls_wR_factor_ref 0.1346 _refine_ls_wR_factor_gt 0.1244 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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 S1 S 0.41866(5) 0.49067(5) 0.13214(3) 0.04202(16) Uani 1 1 d . . . O3 O 1.07027(14) 0.10081(11) 0.09523(7) 0.0315(3) Uani 1 1 d . . . H3O H 1.1519 0.0822 0.1383 0.047 Uiso 1 1 calc R . . N2 N 0.3536(3) 0.3236(3) 0.41895(16) 0.0752(7) Uani 1 1 d . . . N3 N 0.65644(16) 0.53907(13) 0.27459(9) 0.0305(3) Uani 1 1 d . . . N4 N 0.76464(16) 0.14508(15) -0.01551(9) 0.0330(3) Uani 1 1 d . . . H4AN H 0.6656 0.1592 -0.0524 0.040 Uiso 1 1 calc . . . H4BN H 0.8358 0.0859 -0.0297 0.040 Uiso 1 1 calc . . . C1 C 0.97006(18) 0.19598(14) 0.12186(10) 0.0249(3) Uani 1 1 d . . . C2 C 0.91082(18) 0.36447(15) 0.22574(10) 0.0270(3) Uani 1 1 d . . . H2 H 0.9458 0.4146 0.2800 0.032 Uiso 1 1 calc . . . C3 C 0.70104(17) 0.31067(14) 0.09075(10) 0.0243(3) Uani 1 1 d . . . H3 H 0.5926 0.3264 0.0526 0.029 Uiso 1 1 calc . . . C4 C 0.62586(17) 0.47321(14) 0.20064(10) 0.0244(3) Uani 1 1 d . . . C9 C 0.74824(17) 0.38322(14) 0.17132(9) 0.0228(3) Uani 1 1 d . . . C10 C 0.80852(18) 0.21613(14) 0.06501(9) 0.0245(3) Uani 1 1 d . . . C11 C 1.02037(18) 0.27234(16) 0.19999(10) 0.0289(3) Uani 1 1 d . . . H11 H 1.1315 0.2612 0.2363 0.035 Uiso 1 1 calc . . . C12 C 0.5099(2) 0.6143(2) 0.29045(14) 0.0484(5) Uani 1 1 d . . . H12A H 0.5417 0.7107 0.3029 0.058 Uiso 1 1 calc . . . H12B H 0.4766 0.5766 0.3441 0.058 Uiso 1 1 calc . . . C13 C 0.2438(3) 0.2576(3) 0.42810(14) 0.0520(5) Uani 1 1 d . . . C14 C 0.1041(3) 0.1716(2) 0.43833(14) 0.0521(5) Uani 1 1 d . . . H14A H 0.0911 0.0966 0.3950 0.078 Uiso 1 1 calc . . . H14B H -0.0006 0.2252 0.4273 0.078 Uiso 1 1 calc . . . H14C H 0.1272 0.1347 0.4996 0.078 Uiso 1 1 calc . . . C15 C 0.3628(3) 0.6064(3) 0.21176(17) 0.0658(7) Uani 1 1 d . . . H15A H 0.3376 0.6974 0.1843 0.079 Uiso 1 1 calc . . . H15B H 0.2610 0.5733 0.2310 0.079 Uiso 1 1 calc . . . 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 S1 0.0264(2) 0.0456(3) 0.0466(3) -0.01235(19) -0.00752(18) 0.01218(17) O3 0.0279(5) 0.0374(6) 0.0275(5) -0.0014(4) 0.0024(4) 0.0113(4) N2 0.0431(11) 0.0958(17) 0.0796(16) -0.0078(13) -0.0006(10) 0.0020(11) N3 0.0228(6) 0.0319(6) 0.0360(7) -0.0069(5) 0.0052(5) 0.0009(5) N4 0.0271(6) 0.0400(7) 0.0289(7) -0.0097(6) -0.0001(5) 0.0050(5) C1 0.0228(6) 0.0275(7) 0.0247(7) 0.0025(5) 0.0061(5) 0.0038(5) C2 0.0228(6) 0.0303(7) 0.0258(7) -0.0028(6) 0.0012(5) 0.0014(5) C3 0.0201(6) 0.0262(6) 0.0253(7) 0.0022(5) 0.0022(5) -0.0002(5) C4 0.0198(6) 0.0223(6) 0.0297(7) 0.0017(5) 0.0029(5) -0.0004(5) C9 0.0200(6) 0.0219(6) 0.0260(7) 0.0027(5) 0.0040(5) 0.0000(5) C10 0.0232(6) 0.0273(6) 0.0225(6) 0.0015(5) 0.0039(5) -0.0006(5) C11 0.0210(6) 0.0360(8) 0.0269(7) -0.0003(6) -0.0003(5) 0.0038(6) C12 0.0290(8) 0.0557(11) 0.0584(12) -0.0235(10) 0.0050(8) 0.0086(8) C13 0.0376(10) 0.0706(14) 0.0411(10) -0.0121(10) -0.0054(8) 0.0154(10) C14 0.0481(11) 0.0636(13) 0.0426(11) -0.0091(9) 0.0061(8) 0.0140(10) C15 0.0425(11) 0.0872(17) 0.0612(14) -0.0270(12) -0.0020(10) 0.0329(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 S1 C4 1.7729(14) . ? S1 C15 1.796(2) . ? O3 C1 1.3599(17) . ? O3 H3O 0.8400 . ? N2 C13 1.135(3) . ? N3 C4 1.276(2) . ? N3 C12 1.464(2) . ? N4 C10 1.3883(19) . ? N4 H4AN 0.8800 . ? N4 H4BN 0.8800 . ? C1 C11 1.390(2) . ? C1 C10 1.4105(19) . ? C2 C11 1.386(2) . ? C2 C9 1.4007(18) . ? C2 H2 0.9500 . ? C3 C10 1.390(2) . ? C3 C9 1.398(2) . ? C3 H3 0.9500 . ? C4 C9 1.4718(19) . ? C11 H11 0.9500 . ? C12 C15 1.490(3) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.449(3) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? 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 C4 S1 C15 90.68(8) . . ? C1 O3 H3O 109.5 . . ? C4 N3 C12 113.60(13) . . ? C10 N4 H4AN 120.0 . . ? C10 N4 H4BN 120.0 . . ? H4AN N4 H4BN 120.0 . . ? O3 C1 C11 123.34(13) . . ? O3 C1 C10 116.47(13) . . ? C11 C1 C10 120.19(13) . . ? C11 C2 C9 119.59(13) . . ? C11 C2 H2 120.2 . . ? C9 C2 H2 120.2 . . ? C10 C3 C9 121.75(12) . . ? C10 C3 H3 119.1 . . ? C9 C3 H3 119.1 . . ? N3 C4 C9 124.40(13) . . ? N3 C4 S1 116.16(11) . . ? C9 C4 S1 119.42(11) . . ? C3 C9 C2 119.18(13) . . ? C3 C9 C4 120.36(12) . . ? C2 C9 C4 120.39(13) . . ? N4 C10 C3 122.41(13) . . ? N4 C10 C1 119.33(13) . . ? C3 C10 C1 118.22(13) . . ? C2 C11 C1 120.97(13) . . ? C2 C11 H11 119.5 . . ? C1 C11 H11 119.5 . . ? N3 C12 C15 111.74(15) . . ? N3 C12 H12A 109.3 . . ? C15 C12 H12A 109.3 . . ? N3 C12 H12B 109.3 . . ? C15 C12 H12B 109.3 . . ? H12A C12 H12B 107.9 . . ? N2 C13 C14 178.9(2) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C12 C15 S1 107.50(13) . . ? C12 C15 H15A 110.2 . . ? S1 C15 H15A 110.2 . . ? C12 C15 H15B 110.2 . . ? S1 C15 H15B 110.2 . . ? H15A C15 H15B 108.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C12 N3 C4 C9 -176.22(15) . . . . ? C12 N3 C4 S1 2.00(19) . . . . ? C15 S1 C4 N3 1.45(16) . . . . ? C15 S1 C4 C9 179.76(15) . . . . ? C10 C3 C9 C2 2.8(2) . . . . ? C10 C3 C9 C4 -174.35(13) . . . . ? C11 C2 C9 C3 -1.5(2) . . . . ? C11 C2 C9 C4 175.61(14) . . . . ? N3 C4 C9 C3 177.33(14) . . . . ? S1 C4 C9 C3 -0.84(18) . . . . ? N3 C4 C9 C2 0.3(2) . . . . ? S1 C4 C9 C2 -177.92(11) . . . . ? C9 C3 C10 N4 -178.84(14) . . . . ? C9 C3 C10 C1 -1.1(2) . . . . ? O3 C1 C10 N4 -3.4(2) . . . . ? C11 C1 C10 N4 175.98(14) . . . . ? O3 C1 C10 C3 178.78(13) . . . . ? C11 C1 C10 C3 -1.8(2) . . . . ? C9 C2 C11 C1 -1.4(2) . . . . ? O3 C1 C11 C2 -177.56(14) . . . . ? C10 C1 C11 C2 3.1(2) . . . . ? C4 N3 C12 C15 -5.4(3) . . . . ? N3 C12 C15 S1 6.0(3) . . . . ? C4 S1 C15 C12 -4.2(2) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 30.01 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.343 _refine_diff_density_min -0.397 _refine_diff_density_rms 0.053 data_as7 _database_code_depnum_ccdc_archive 'CCDC 838884' #TrackingRef '6701_web_deposit_cif_file_0_ArturStefankiewicz_1313060397.AS13.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H9 N O3' _chemical_formula_weight 167.16 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 10.1980(8) _cell_length_b 8.7310(12) _cell_length_c 17.664(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1572.8(3) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1848 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.412 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.109 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method '/p scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3185 _diffrn_reflns_av_R_equivalents 0.0911 _diffrn_reflns_av_sigmaI/netI 0.1340 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 27.49 _reflns_number_total 1774 _reflns_number_gt 868 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo (Nonius B.V., 1998)' _computing_data_reduction 'Denzo (Nonius B.V., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON 98 (Spek, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0651P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1774 _refine_ls_number_parameters 119 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1859 _refine_ls_R_factor_gt 0.0773 _refine_ls_wR_factor_ref 0.1672 _refine_ls_wR_factor_gt 0.1358 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4518(3) 0.0936(4) -0.11279(16) 0.0445(9) Uani 1 1 d . . . H1A H 0.3700 0.0348 -0.1146 0.067 Uiso 1 1 calc R . . H1B H 0.5266 0.0238 -0.1178 0.067 Uiso 1 1 calc R . . H1C H 0.4531 0.1679 -0.1544 0.067 Uiso 1 1 calc R . . C2 C 0.3755(3) 0.2894(4) -0.03106(16) 0.0344(8) Uani 1 1 d . . . C3 C 0.3971(3) 0.3649(4) 0.04277(16) 0.0323(8) Uani 1 1 d . . . C4 C 0.5028(3) 0.3245(4) 0.08809(16) 0.0317(8) Uani 1 1 d . . . H4 H 0.5592 0.2440 0.0723 0.038 Uiso 1 1 calc . . . C5 C 0.5275(3) 0.3984(4) 0.15539(16) 0.0345(8) Uani 1 1 d . . . C6 C 0.4451(3) 0.5181(4) 0.17820(16) 0.0353(8) Uani 1 1 d . . . C7 C 0.3377(3) 0.5576(4) 0.13391(17) 0.0406(9) Uani 1 1 d . . . H7 H 0.2799 0.6363 0.1502 0.049 Uiso 1 1 calc . . . C8 C 0.3147(3) 0.4829(4) 0.06617(16) 0.0386(9) Uani 1 1 d . . . H8 H 0.2424 0.5122 0.0355 0.046 Uiso 1 1 calc . . . N2 N 0.6334(3) 0.3526(4) 0.20285(16) 0.0401(8) Uani 1 1 d . . . O1 O 0.29229(19) 0.3234(3) -0.07691(11) 0.0432(7) Uani 1 1 d . . . O2 O 0.46030(19) 0.1735(3) -0.04141(10) 0.0409(6) Uani 1 1 d . . . O3 O 0.4786(2) 0.5893(3) 0.24374(12) 0.0487(7) Uani 1 1 d . . . H3O H 0.4278 0.6635 0.2513 0.073 Uiso 1 1 calc R . . H1N H 0.697(3) 0.322(3) 0.1754(14) 0.028(9) Uiso 1 1 d . . . H2N H 0.653(3) 0.429(5) 0.2353(19) 0.069(13) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.044(2) 0.050(2) 0.040(2) -0.0069(17) -0.0012(14) 0.0003(18) C2 0.0260(16) 0.037(2) 0.0400(19) 0.0032(16) 0.0061(14) -0.0071(16) C3 0.0289(17) 0.033(2) 0.0352(17) 0.0033(15) 0.0029(14) -0.0050(15) C4 0.0282(17) 0.031(2) 0.0358(17) 0.0045(15) 0.0057(12) 0.0020(15) C5 0.0329(17) 0.039(2) 0.0313(18) 0.0060(16) -0.0007(13) -0.0034(16) C6 0.0408(19) 0.037(2) 0.0283(18) -0.0005(15) 0.0037(14) -0.0057(17) C7 0.0410(19) 0.041(2) 0.039(2) 0.0014(16) 0.0035(15) 0.0068(16) C8 0.0308(17) 0.043(2) 0.042(2) 0.0067(17) -0.0004(14) -0.0001(17) N2 0.0339(17) 0.050(2) 0.0363(18) -0.0029(16) 0.0027(14) 0.0038(16) O1 0.0342(12) 0.0520(17) 0.0433(12) 0.0005(11) -0.0069(10) -0.0005(12) O2 0.0397(13) 0.0442(16) 0.0387(12) -0.0061(11) -0.0040(9) 0.0063(12) O3 0.0585(16) 0.0499(19) 0.0375(13) -0.0057(12) -0.0059(11) 0.0080(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O2 1.444(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 O1 1.210(3) . ? C2 O2 1.344(4) . ? C2 C3 1.478(4) . ? C3 C4 1.388(4) . ? C3 C8 1.392(4) . ? C4 C5 1.376(4) . ? C4 H4 0.9500 . ? C5 C6 1.400(4) . ? C5 N2 1.425(4) . ? C6 O3 1.358(3) . ? C6 C7 1.389(4) . ? C7 C8 1.383(4) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? N2 H1N 0.85(3) . ? N2 H2N 0.90(4) . ? O3 H3O 0.8400 . ? 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 O2 C1 H1A 109.5 . . ? O2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O1 C2 O2 123.0(3) . . ? O1 C2 C3 125.9(3) . . ? O2 C2 C3 111.1(3) . . ? C4 C3 C8 119.1(3) . . ? C4 C3 C2 120.7(3) . . ? C8 C3 C2 120.1(3) . . ? C5 C4 C3 121.4(3) . . ? C5 C4 H4 119.3 . . ? C3 C4 H4 119.3 . . ? C4 C5 C6 119.3(3) . . ? C4 C5 N2 121.0(3) . . ? C6 C5 N2 119.7(3) . . ? O3 C6 C7 124.4(3) . . ? O3 C6 C5 115.9(3) . . ? C7 C6 C5 119.8(3) . . ? C8 C7 C6 120.2(3) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C7 C8 C3 120.2(3) . . ? C7 C8 H8 119.9 . . ? C3 C8 H8 119.9 . . ? C5 N2 H1N 109.1(17) . . ? C5 N2 H2N 110(2) . . ? H1N N2 H2N 115(3) . . ? C2 O2 C1 116.4(2) . . ? C6 O3 H3O 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C2 C3 C4 -174.5(3) . . . . ? O2 C2 C3 C4 6.3(4) . . . . ? O1 C2 C3 C8 2.5(5) . . . . ? O2 C2 C3 C8 -176.6(3) . . . . ? C8 C3 C4 C5 0.0(4) . . . . ? C2 C3 C4 C5 177.1(3) . . . . ? C3 C4 C5 C6 -0.7(5) . . . . ? C3 C4 C5 N2 177.8(3) . . . . ? C4 C5 C6 O3 -177.6(3) . . . . ? N2 C5 C6 O3 3.9(4) . . . . ? C4 C5 C6 C7 1.9(5) . . . . ? N2 C5 C6 C7 -176.7(3) . . . . ? O3 C6 C7 C8 177.1(3) . . . . ? C5 C6 C7 C8 -2.3(5) . . . . ? C6 C7 C8 C3 1.6(5) . . . . ? C4 C3 C8 C7 -0.4(5) . . . . ? C2 C3 C8 C7 -177.5(3) . . . . ? O1 C2 O2 C1 2.8(4) . . . . ? C3 C2 O2 C1 -178.1(2) . . . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.193 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.052