# 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_2012ln0014a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H10 N3 O4 P' _chemical_formula_weight 207.13 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M I2/a _symmetry_space_group_name_hall '-I 2ya' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z' 'x+1/2, y+1/2, z+1/2' '-x+1, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z' '-x+1/2, -y+1/2, -z+1/2' 'x, -y+1/2, z+1/2' _cell_length_a 14.6204(10) _cell_length_b 7.6631(4) _cell_length_c 16.002(2) _cell_angle_alpha 90.00 _cell_angle_beta 97.234(9) _cell_angle_gamma 90.00 _cell_volume 1778.6(3) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 7445 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description platelet _exptl_crystal_colour colourless _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.547 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 0.298 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.770 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ; CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator Confocal _diffrn_measurement_device_type ; Rigaku Saturn724+ (2x2 bin mode) ; _diffrn_measurement_method 'profile data from \w-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8398 _diffrn_reflns_av_R_equivalents 0.0424 _diffrn_reflns_av_sigmaI/netI 0.0366 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2030 _reflns_number_gt 1718 _reflns_threshold_expression >2\s(I) __computing_data_collection ; CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011) ; _computing_structure_solution 'SUPERFLIP (Palatinus & Chapuis, 2007)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; MERCURY (Bruno, Cole, Edgington, Kessler, Macrae, McCabe, Pearson and Taylor, 2002) ; _computing_publication_material 'WINGX (Farrugia, 1998)' _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^ > 2\s(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^)+(0.0522P)^2^+1.0309P] 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 2030 _refine_ls_number_parameters 120 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0405 _refine_ls_R_factor_gt 0.0332 _refine_ls_wR_factor_ref 0.1008 _refine_ls_wR_factor_gt 0.0973 _refine_ls_goodness_of_fit_ref 1.110 _refine_ls_restrained_S_all 1.110 _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 C2 C 0.52064(11) 0.6821(2) 0.09769(11) 0.0194(4) Uani 1 1 d . . . H2 H 0.5591 0.6270 0.1423 0.023 Uiso 1 1 calc R . . C3 C 0.55130(11) 0.6978(2) 0.02046(11) 0.0176(3) Uani 1 1 d . . . C4 C 0.49132(11) 0.7780(2) -0.04581(10) 0.0165(3) Uani 1 1 d . . . C5 C 0.40660(11) 0.8440(2) -0.02692(11) 0.0189(3) Uani 1 1 d . . . H5 H 0.3667 0.9029 -0.0692 0.023 Uiso 1 1 calc R . . C6 C 0.38119(11) 0.8240(2) 0.05170(11) 0.0201(4) Uani 1 1 d . . . H6 H 0.3235 0.8679 0.0637 0.024 Uiso 1 1 calc R . . N1 N 0.43743(10) 0.74263(19) 0.11209(9) 0.0190(3) Uani 1 1 d . . . H1 H 0.4197 0.7284 0.1622 0.023 Uiso 1 1 calc R . . N2 N 0.63667(10) 0.6374(2) 0.00683(10) 0.0246(4) Uani 1 1 d . . . H2A H 0.6729 0.5875 0.0481 0.030 Uiso 1 1 calc R . . H2B H 0.6551 0.6487 -0.0432 0.030 Uiso 1 1 calc R . . N3 N 0.51574(10) 0.79270(19) -0.12340(9) 0.0206(3) Uani 1 1 d . . . H3A H 0.4785 0.8442 -0.1634 0.025 Uiso 1 1 calc R . . H3B H 0.5690 0.7508 -0.1343 0.025 Uiso 1 1 calc R . . O4 O 0.26626(8) 0.44032(16) 0.32061(7) 0.0212(3) Uani 1 1 d . . . H4 H 0.2405 0.3422 0.3162 0.032 Uiso 1 1 calc R . . O3 O 0.19868(8) 0.56791(16) 0.18074(8) 0.0223(3) Uani 1 1 d . . . H3 H 0.1805 0.6574 0.2041 0.033 Uiso 1 1 calc R . . O2 O 0.35812(7) 0.64777(15) 0.24988(7) 0.0174(3) Uani 1 1 d . . . O1 O 0.32184(8) 0.35035(15) 0.18263(8) 0.0207(3) Uani 1 1 d . . . P1 P 0.29055(3) 0.49943(5) 0.23261(3) 0.01441(14) 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 C2 0.0177(8) 0.0194(8) 0.0199(9) 0.0013(7) -0.0022(6) 0.0000(6) C3 0.0153(7) 0.0170(8) 0.0193(9) 0.0004(6) -0.0027(6) -0.0012(6) C4 0.0154(7) 0.0161(8) 0.0169(9) -0.0002(6) -0.0028(6) -0.0028(6) C5 0.0169(7) 0.0194(8) 0.0195(9) 0.0003(6) -0.0018(6) 0.0010(6) C6 0.0161(7) 0.0212(9) 0.0219(9) -0.0016(7) -0.0013(6) -0.0004(6) N1 0.0199(7) 0.0222(7) 0.0148(7) 0.0005(5) 0.0014(5) -0.0013(5) N2 0.0172(7) 0.0367(9) 0.0193(8) 0.0045(6) -0.0005(6) 0.0077(6) N3 0.0166(7) 0.0278(8) 0.0166(8) 0.0022(6) -0.0009(5) 0.0041(6) O4 0.0274(6) 0.0189(6) 0.0173(6) -0.0021(5) 0.0028(5) -0.0077(5) O3 0.0202(6) 0.0183(7) 0.0255(7) -0.0056(5) -0.0076(5) 0.0004(5) O2 0.0154(5) 0.0188(6) 0.0179(6) -0.0015(5) 0.0008(4) -0.0041(4) O1 0.0197(6) 0.0192(6) 0.0240(7) -0.0047(5) 0.0061(5) -0.0029(5) P1 0.0131(2) 0.0152(2) 0.0144(2) -0.00125(15) -0.00044(16) -0.00183(14) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C2 N1 1.349(2) . ? C2 C3 1.372(2) . ? C2 H2 0.9500 . ? C3 N2 1.374(2) . ? C3 C4 1.428(2) . ? C4 N3 1.339(2) . ? C4 C5 1.405(2) . ? C5 C6 1.365(2) . ? C5 H5 0.9500 . ? C6 N1 1.341(2) . ? C6 H6 0.9500 . ? N1 H1 0.8800 . ? N2 H2A 0.8800 . ? N2 H2B 0.8800 . ? N3 H3A 0.8800 . ? N3 H3B 0.8800 . ? O4 P1 1.5621(12) . ? O4 H4 0.8400 . ? O3 P1 1.5771(12) . ? O3 H3 0.8400 . ? O2 P1 1.5087(11) . ? O1 P1 1.4988(12) . ? 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 N1 C2 C3 121.86(16) . . ? N1 C2 H2 119.1 . . ? C3 C2 H2 119.1 . . ? C2 C3 N2 121.32(15) . . ? C2 C3 C4 117.85(15) . . ? N2 C3 C4 120.82(15) . . ? N3 C4 C5 120.96(15) . . ? N3 C4 C3 120.95(15) . . ? C5 C4 C3 118.08(15) . . ? C6 C5 C4 120.51(16) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? N1 C6 C5 120.21(15) . . ? N1 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C6 N1 C2 121.41(15) . . ? C6 N1 H1 119.3 . . ? C2 N1 H1 119.3 . . ? C3 N2 H2A 120.0 . . ? C3 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? C4 N3 H3A 120.0 . . ? C4 N3 H3B 120.0 . . ? H3A N3 H3B 120.0 . . ? P1 O4 H4 109.5 . . ? P1 O3 H3 109.5 . . ? O1 P1 O2 115.80(7) . . ? O1 P1 O4 112.30(7) . . ? O2 P1 O4 105.74(7) . . ? O1 P1 O3 105.65(7) . . ? O2 P1 O3 109.90(7) . . ? O4 P1 O3 107.20(7) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C2 C3 N2 179.21(16) . . . . ? N1 C2 C3 C4 -1.2(2) . . . . ? C2 C3 C4 N3 -177.93(15) . . . . ? N2 C3 C4 N3 1.7(2) . . . . ? C2 C3 C4 C5 3.2(2) . . . . ? N2 C3 C4 C5 -177.24(15) . . . . ? N3 C4 C5 C6 178.13(16) . . . . ? C3 C4 C5 C6 -3.0(2) . . . . ? C4 C5 C6 N1 0.7(3) . . . . ? C5 C6 N1 C2 1.4(3) . . . . ? C3 C2 N1 C6 -1.1(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.293 _refine_diff_density_min -0.407 _refine_diff_density_rms 0.060 _database_code_depnum_ccdc_archive 'CCDC 959232' ####################################################################### # # 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_4-aminopyridinium_sulfate _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 4-aminopyridinium_hydrogenosulfate _chemical_melting_point ? _chemical_formula_moiety 'C5 H7 N2, H O4 S' _chemical_formula_sum 'C5 H8 N2 O4 S' _chemical_formula_weight 192.19 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/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 10.9507(4) _cell_length_b 6.4615(2) _cell_length_c 11.2614(3) _cell_angle_alpha 90.00 _cell_angle_beta 102.988(2) _cell_angle_gamma 90.00 _cell_volume 776.45(4) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 7281 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.644 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 400 _exptl_absorpt_coefficient_mu 0.393 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8127 _exptl_absorpt_correction_T_max 0.9730 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; "Platon erroniously reports a pseudo mirror plane on this structure by neglecting a proton" ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius Roper CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10095 _diffrn_reflns_av_R_equivalents 0.0298 _diffrn_reflns_av_sigmaI/netI 0.0239 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.95 _diffrn_reflns_theta_max 27.49 _reflns_number_total 1776 _reflns_number_gt 1489 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^)+(0.0556P)^2^+0.2811P] 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 1776 _refine_ls_number_parameters 129 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0409 _refine_ls_R_factor_gt 0.0330 _refine_ls_wR_factor_ref 0.1000 _refine_ls_wR_factor_gt 0.0944 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _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 H3 H 0.7710(19) 0.740(2) 0.8277(19) 0.020(5) Uiso 1 1 d . . . H2A H 0.545(2) 0.746(2) 0.807(2) 0.028(6) Uiso 1 1 d . . . H2B H 0.459(2) 0.753(2) 0.6830(19) 0.021(5) Uiso 1 1 d . . . H3A H 0.782(3) 0.012(4) 0.280(2) 0.081(9) Uiso 1 1 d . . . H6 H 0.691(2) 0.753(2) 0.398(2) 0.031(6) Uiso 1 1 d . . . N1 N 0.82204(13) 0.74123(17) 0.55248(13) 0.0192(3) Uani 1 1 d . . . H1 H 0.8836 0.7398 0.5140 0.023 Uiso 1 1 calc R . . N2 N 0.53479(13) 0.74902(19) 0.73061(14) 0.0212(3) Uani 1 1 d . . . C2 C 0.84861(15) 0.7377(2) 0.67608(15) 0.0188(3) Uani 1 1 d . . . H2 H 0.9336 0.7338 0.7197 0.023 Uiso 1 1 calc R . . C3 C 0.75599(15) 0.7397(2) 0.73857(15) 0.0170(3) Uani 1 1 d . . . C4 C 0.62844(15) 0.74559(18) 0.67318(14) 0.0143(3) Uani 1 1 d . . . C5 C 0.60486(14) 0.74835(19) 0.54413(13) 0.0159(3) Uani 1 1 d . . . H5 H 0.5212 0.7513 0.4971 0.019 Uiso 1 1 calc R . . C6 C 0.70251(16) 0.7468(2) 0.48803(15) 0.0190(3) Uani 1 1 d . . . O1 O 0.93860(10) 0.26497(14) 0.50768(9) 0.0163(3) Uani 1 1 d . . . O2 O 0.83799(9) 0.42397(17) 0.31773(9) 0.0212(3) Uani 1 1 d . . . O3 O 0.85606(10) 0.05182(16) 0.33751(9) 0.0208(3) Uani 1 1 d . . . O4 O 0.71280(10) 0.24032(14) 0.43535(10) 0.0172(3) Uani 1 1 d . . . S1 S 0.83352(3) 0.25598(4) 0.40391(3) 0.01132(15) 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 N1 0.0169(7) 0.0217(7) 0.0224(7) -0.0001(5) 0.0116(6) 0.0000(4) N2 0.0122(7) 0.0382(9) 0.0138(7) 0.0002(5) 0.0041(5) -0.0001(5) C2 0.0127(7) 0.0195(7) 0.0236(8) 0.0013(5) 0.0030(6) 0.0002(5) C3 0.0151(7) 0.0196(7) 0.0154(7) 0.0006(5) 0.0014(6) -0.0006(5) C4 0.0130(7) 0.0142(7) 0.0156(7) 0.0003(5) 0.0031(6) -0.0005(5) C5 0.0146(7) 0.0178(7) 0.0150(8) -0.0002(5) 0.0027(6) -0.0014(5) C6 0.0211(8) 0.0200(8) 0.0168(8) -0.0007(5) 0.0061(6) -0.0006(5) O1 0.0120(5) 0.0261(6) 0.0100(5) -0.0002(4) 0.0005(4) -0.0004(4) O2 0.0190(5) 0.0241(6) 0.0191(5) 0.0090(4) 0.0012(4) -0.0014(4) O3 0.0165(5) 0.0228(6) 0.0222(5) -0.0085(4) 0.0023(4) 0.0040(4) O4 0.0096(5) 0.0241(6) 0.0184(5) -0.0017(4) 0.0042(4) -0.0004(4) S1 0.0087(2) 0.0147(2) 0.0101(2) 0.00018(11) 0.00109(15) 0.00056(11) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 N1 C6 1.347(2) . ? N1 C2 1.357(2) . ? N1 H1 0.8800 . ? N2 C4 1.330(2) . ? N2 H2A 0.84(2) . ? N2 H2B 0.88(2) . ? C2 C3 1.358(2) . ? C2 H2 0.9500 . ? C3 C4 1.426(2) . ? C3 H3 0.98(2) . ? C4 C5 1.418(2) . ? C5 C6 1.359(2) . ? C5 H5 0.9500 . ? C6 H6 0.99(2) . ? O1 S1 1.4452(10) . ? O2 S1 1.4642(10) . ? O3 S1 1.5631(10) . ? O3 H3A 0.95(3) . ? O4 S1 1.4469(11) . ? 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 C6 N1 C2 120.77(14) . . ? C6 N1 H1 119.6 . . ? C2 N1 H1 119.6 . . ? C4 N2 H2A 123.7(16) . . ? C4 N2 H2B 115.2(14) . . ? H2A N2 H2B 121(2) . . ? N1 C2 C3 121.23(15) . . ? N1 C2 H2 119.4 . . ? C3 C2 H2 119.4 . . ? C2 C3 C4 119.45(15) . . ? C2 C3 H3 123.9(12) . . ? C4 C3 H3 116.6(12) . . ? N2 C4 C5 121.03(15) . . ? N2 C4 C3 121.49(15) . . ? C5 C4 C3 117.47(15) . . ? C6 C5 C4 119.69(15) . . ? C6 C5 H5 120.2 . . ? C4 C5 H5 120.2 . . ? N1 C6 C5 121.38(16) . . ? N1 C6 H6 115.6(14) . . ? C5 C6 H6 123.0(14) . . ? S1 O3 H3A 110.6(15) . . ? O1 S1 O4 114.22(6) . . ? O1 S1 O2 111.53(6) . . ? O4 S1 O2 112.49(6) . . ? O1 S1 O3 103.77(6) . . ? O4 S1 O3 108.01(6) . . ? O2 S1 O3 106.03(6) . . ? 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 N2 H2A O1 0.84(2) 2.06(2) 2.8975(18) 174.5(17) 2_656 N2 H2B O4 0.88(2) 2.05(2) 2.9276(18) 177.2(19) 3_666 O3 H3A O2 0.95(3) 1.62(3) 2.5660(15) 175(2) 2_645 N1 H1 O1 0.88 2.02 2.8511(17) 158.1 3_766 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.313 _refine_diff_density_min -0.574 _refine_diff_density_rms 0.064 _database_code_depnum_ccdc_archive 'CCDC 959233' ####################################################################### # # 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_2012ln0047a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H7 N3 O3' _chemical_formula_weight 157.14 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 9.1718(6) _cell_length_b 6.9081(4) _cell_length_c 10.8243(7) _cell_angle_alpha 90.00 _cell_angle_beta 93.617(7) _cell_angle_gamma 90.00 _cell_volume 684.46(7) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3350 _cell_measurement_theta_min 3.5 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.525 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 328 _exptl_absorpt_coefficient_mu 0.127 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.847 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ; CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator Confocal _diffrn_measurement_device_type ; Rigaku Saturn724+ (2x2 bin mode) ; _diffrn_detector_area_resol_mean 28.5714 _diffrn_measurement_method 'profile data from \w-scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3555 _diffrn_reflns_av_R_equivalents 0.0256 _diffrn_reflns_av_sigmaI/netI 0.0332 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.50 _diffrn_reflns_theta_max 27.47 _reflns_number_total 1542 _reflns_number_gt 1377 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011) ; _computing_structure_solution 'SUPERFLIP (Palatinus & Chapuis, 2007)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; MERCURY (Bruno, Cole, Edgington, Kessler, Macrae, McCabe, Pearson and Taylor, 2002) ; _computing_publication_material 'WINGX (Farrugia, 1998)' _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^ > 2\s(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^)+(0.0093P)^2^+2.2953P] 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 1542 _refine_ls_number_parameters 100 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0579 _refine_ls_R_factor_gt 0.0518 _refine_ls_wR_factor_ref 0.1433 _refine_ls_wR_factor_gt 0.1411 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _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 0.77735(18) 0.5552(3) 0.24367(15) 0.0174(4) Uani 1 1 d . . . O2 O 0.8525(2) 0.6511(3) 0.06721(17) 0.0226(4) Uani 1 1 d . . . O3 O 0.61997(19) 0.6289(3) 0.09358(17) 0.0235(5) Uani 1 1 d . . . N1 N 0.9254(2) 0.0914(3) 0.19520(19) 0.0173(5) Uani 1 1 d . . . H1 H 1.0205 0.0853 0.2119 0.021 Uiso 1 1 calc R . . N10 N 0.7502(2) 0.6124(3) 0.13330(18) 0.0146(4) Uani 1 1 d . . . C5 C 0.6865(3) 0.0461(3) 0.2600(2) 0.0153(5) Uani 1 1 d . . . H5 H 0.6237 0.0046 0.3213 0.018 Uiso 1 1 calc R . . C6 C 0.8341(3) 0.0358(4) 0.2819(2) 0.0171(5) Uani 1 1 d . . . H6 H 0.8736 -0.0113 0.3594 0.021 Uiso 1 1 calc R . . C4 C 0.6269(3) 0.1191(3) 0.1451(2) 0.0140(5) Uani 1 1 d . . . C2 C 0.8730(3) 0.1559(4) 0.0837(2) 0.0166(5) Uani 1 1 d . . . H2 H 0.9392 0.1916 0.0236 0.020 Uiso 1 1 calc R . . C3 C 0.7265(3) 0.1709(4) 0.0556(2) 0.0155(5) Uani 1 1 d . . . H3 H 0.6911 0.2159 -0.0236 0.019 Uiso 1 1 calc R . . N4 N 0.4833(2) 0.1360(3) 0.12182(19) 0.0177(5) Uani 1 1 d . . . H4A H 0.4482 0.1801 0.0497 0.021 Uiso 1 1 calc R . . H4B H 0.4233 0.1031 0.1786 0.021 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 0.0174(8) 0.0232(9) 0.0114(8) 0.0018(7) 0.0000(6) 0.0000(7) O2 0.0211(9) 0.0266(10) 0.0210(9) 0.0000(8) 0.0083(7) -0.0054(8) O3 0.0157(9) 0.0291(10) 0.0249(10) 0.0041(8) -0.0045(7) -0.0002(8) N1 0.0135(9) 0.0183(10) 0.0199(10) -0.0013(8) -0.0005(8) -0.0006(8) N10 0.0151(9) 0.0145(10) 0.0142(9) -0.0018(8) 0.0009(7) -0.0016(8) C5 0.0175(11) 0.0136(11) 0.0151(11) 0.0001(9) 0.0033(9) -0.0019(9) C6 0.0217(12) 0.0149(11) 0.0146(11) 0.0009(9) -0.0009(9) 0.0010(9) C4 0.0155(11) 0.0109(10) 0.0157(11) -0.0034(9) 0.0014(8) -0.0015(9) C2 0.0183(12) 0.0159(11) 0.0158(11) -0.0019(9) 0.0039(9) -0.0032(9) C3 0.0183(11) 0.0142(11) 0.0142(11) 0.0000(9) 0.0018(9) -0.0010(9) N4 0.0148(10) 0.0227(11) 0.0156(10) -0.0006(8) 0.0020(7) -0.0002(8) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 N10 1.268(3) . ? O2 N10 1.244(3) . ? O3 N10 1.249(3) . ? N1 C2 1.347(3) . ? N1 C6 1.352(3) . ? N1 H1 0.8800 . ? C5 C6 1.362(3) . ? C5 C4 1.419(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C4 N4 1.330(3) . ? C4 C3 1.418(3) . ? C2 C3 1.363(3) . ? C2 H2 0.9500 . ? C3 H3 0.9500 . ? N4 H4A 0.8800 . ? N4 H4B 0.8800 . ? 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 C2 N1 C6 121.0(2) . . ? C2 N1 H1 119.5 . . ? C6 N1 H1 119.5 . . ? O2 N10 O3 121.5(2) . . ? O2 N10 O1 119.9(2) . . ? O3 N10 O1 118.64(19) . . ? C6 C5 C4 119.7(2) . . ? C6 C5 H5 120.2 . . ? C4 C5 H5 120.2 . . ? N1 C6 C5 121.1(2) . . ? N1 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? N4 C4 C3 121.4(2) . . ? N4 C4 C5 121.3(2) . . ? C3 C4 C5 117.3(2) . . ? N1 C2 C3 121.1(2) . . ? N1 C2 H2 119.5 . . ? C3 C2 H2 119.5 . . ? C2 C3 C4 119.8(2) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C4 N4 H4A 120.0 . . ? C4 N4 H4B 120.0 . . ? H4A N4 H4B 120.0 . . ? 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 C2 N1 C6 C5 -1.0(4) . . . . ? C4 C5 C6 N1 -1.0(4) . . . . ? C6 C5 C4 N4 -178.2(2) . . . . ? C6 C5 C4 C3 2.6(3) . . . . ? C6 N1 C2 C3 1.3(4) . . . . ? N1 C2 C3 C4 0.4(4) . . . . ? N4 C4 C3 C2 178.5(2) . . . . ? C5 C4 C3 C2 -2.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.294 _refine_diff_density_min -0.324 _refine_diff_density_rms 0.062 _database_code_depnum_ccdc_archive 'CCDC 959234' ####################################################################### # # 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_2012ln0016 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H11 N2 O5 P' _chemical_formula_weight 210.13 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.2785(4) _cell_length_b 7.9141(4) _cell_length_c 8.9022(6) _cell_angle_alpha 77.651(6) _cell_angle_beta 71.756(5) _cell_angle_gamma 67.405(5) _cell_volume 447.07(4) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 5179 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 27.4 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.561 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 220 _exptl_absorpt_coefficient_mu 0.302 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.955 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ; CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 'Rigaku R-AXIS SPIDER IP' _diffrn_measurement_method 'profile data from oscillation \w-scans' _diffrn_detector_area_resol_mean 10 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5766 _diffrn_reflns_av_R_equivalents 0.0122 _diffrn_reflns_av_sigmaI/netI 0.0131 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 27.44 _reflns_number_total 2031 _reflns_number_gt 1842 _reflns_threshold_expression >2\s(I) __computing_data_collection ; CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011) ; _computing_structure_solution 'Superflip (Palatinus & Chapuis, 2007)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997) ' _computing_molecular_graphics ; MERCURY (Bruno, Cole, Edgington, Kessler, Macrae, Pearson and Taylor, 2002) ; _computing_publication_material 'WINGX (Farrugia, 1998)' _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^ > 2\s(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^)+(0.0398P)^2^+0.2160P] 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 2031 _refine_ls_number_parameters 128 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0308 _refine_ls_R_factor_gt 0.0270 _refine_ls_wR_factor_ref 0.0791 _refine_ls_wR_factor_gt 0.0726 _refine_ls_goodness_of_fit_ref 1.147 _refine_ls_restrained_S_all 1.147 _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 C2 C 0.5615(2) 0.19801(19) 0.52900(16) 0.0166(3) Uani 1 1 d . . . H2 H 0.4531 0.2758 0.6022 0.020 Uiso 1 1 calc R . . C3 C 0.6793(2) 0.02954(19) 0.58415(16) 0.0157(3) Uani 1 1 d . . . H3 H 0.6540 -0.0087 0.6951 0.019 Uiso 1 1 calc R . . C4 C 0.8397(2) -0.08843(18) 0.47570(15) 0.0139(3) Uani 1 1 d . . . C5 C 0.8724(2) -0.02210(19) 0.31203(16) 0.0162(3) Uani 1 1 d . . . H5 H 0.9792 -0.0962 0.2354 0.019 Uiso 1 1 calc R . . C6 C 0.7500(2) 0.14842(19) 0.26481(16) 0.0176(3) Uani 1 1 d . . . H6 H 0.7731 0.1924 0.1549 0.021 Uiso 1 1 calc R . . N1 N 0.59638(18) 0.25603(16) 0.37181(14) 0.0171(2) Uani 1 1 d . . . H1 H 0.5183 0.3651 0.3386 0.020 Uiso 1 1 calc R . . N4 N 0.95534(18) -0.25664(16) 0.52493(14) 0.0176(2) Uani 1 1 d . . . H4B H 1.0534 -0.3278 0.4552 0.021 Uiso 1 1 calc R . . H4C H 0.9333 -0.2961 0.6270 0.021 Uiso 1 1 calc R . . O1 O 0.14974(14) 0.38565(13) 1.13397(11) 0.0154(2) Uani 1 1 d . . . O2 O 0.50956(14) 0.21826(13) 0.96881(12) 0.0170(2) Uani 1 1 d . . . O1W O 0.69262(16) 0.43463(14) 0.73641(12) 0.0164(2) Uani 1 1 d . . . O3 O 0.22647(15) 0.39520(14) 0.83756(11) 0.0203(2) Uani 1 1 d . . . H3A H 0.1018 0.4622 0.8583 0.030 Uiso 1 1 calc R . . O4 O 0.21507(15) 0.10355(13) 1.01381(13) 0.0196(2) Uani 1 1 d . . . H4A H 0.3185 0.0074 1.0140 0.029 Uiso 1 1 calc R . . P1 P 0.27994(5) 0.27605(4) 0.99386(4) 0.01217(11) Uani 1 1 d . . . H1W H 0.738(3) 0.483(3) 0.781(3) 0.033(6) Uiso 1 1 d . . . H2W H 0.642(3) 0.362(3) 0.804(3) 0.032(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 C2 0.0148(6) 0.0194(7) 0.0156(6) -0.0062(5) -0.0010(5) -0.0058(5) C3 0.0162(6) 0.0203(7) 0.0110(6) -0.0014(5) -0.0020(5) -0.0080(5) C4 0.0139(6) 0.0161(6) 0.0139(6) -0.0011(5) -0.0039(5) -0.0073(5) C5 0.0164(6) 0.0182(6) 0.0119(6) -0.0029(5) -0.0006(5) -0.0054(5) C6 0.0212(7) 0.0195(7) 0.0123(6) 0.0005(5) -0.0043(5) -0.0083(6) N1 0.0180(6) 0.0146(5) 0.0176(6) -0.0005(4) -0.0061(4) -0.0039(4) N4 0.0181(6) 0.0164(6) 0.0139(5) 0.0004(4) -0.0026(4) -0.0033(5) O1 0.0151(5) 0.0157(5) 0.0125(4) -0.0019(4) -0.0040(4) -0.0015(4) O2 0.0126(5) 0.0129(4) 0.0216(5) 0.0019(4) -0.0037(4) -0.0028(4) O1W 0.0180(5) 0.0162(5) 0.0151(5) -0.0010(4) -0.0030(4) -0.0073(4) O3 0.0160(5) 0.0220(5) 0.0104(4) 0.0007(4) -0.0006(4) 0.0035(4) O4 0.0124(5) 0.0135(5) 0.0316(6) -0.0038(4) -0.0064(4) -0.0017(4) P1 0.01081(17) 0.01125(17) 0.01128(17) 0.00000(12) -0.00243(12) -0.00134(12) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C2 N1 1.3513(18) . ? C2 C3 1.364(2) . ? C2 H2 0.9500 . ? C3 C4 1.4173(19) . ? C3 H3 0.9500 . ? C4 N4 1.3391(18) . ? C4 C5 1.4166(18) . ? C5 C6 1.364(2) . ? C5 H5 0.9500 . ? C6 N1 1.3533(18) . ? C6 H6 0.9500 . ? N1 H1 0.8800 . ? N4 H4B 0.8800 . ? N4 H4C 0.8800 . ? O1 P1 1.5156(10) . ? O2 P1 1.5083(10) . ? O1W H1W 0.81(2) . ? O1W H2W 0.84(2) . ? O3 P1 1.5724(10) . ? O3 H3A 0.8400 . ? O4 P1 1.5675(10) . ? O4 H4A 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 N1 C2 C3 121.02(13) . . ? N1 C2 H2 119.5 . . ? C3 C2 H2 119.5 . . ? C2 C3 C4 119.92(12) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? N4 C4 C5 120.98(12) . . ? N4 C4 C3 121.67(12) . . ? C5 C4 C3 117.36(12) . . ? C6 C5 C4 119.80(13) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? N1 C6 C5 121.12(12) . . ? N1 C6 H6 119.4 . . ? C5 C6 H6 119.4 . . ? C2 N1 C6 120.78(12) . . ? C2 N1 H1 119.6 . . ? C6 N1 H1 119.6 . . ? C4 N4 H4B 120.0 . . ? C4 N4 H4C 120.0 . . ? H4B N4 H4C 120.0 . . ? H1W O1W H2W 108(2) . . ? P1 O3 H3A 109.5 . . ? P1 O4 H4A 109.5 . . ? O2 P1 O1 115.38(6) . . ? O2 P1 O4 110.41(5) . . ? O1 P1 O4 108.24(6) . . ? O2 P1 O3 107.35(6) . . ? O1 P1 O3 108.79(5) . . ? O4 P1 O3 106.29(6) . . ? 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 N1 C2 C3 C4 -0.8(2) . . . . ? C2 C3 C4 N4 -178.30(12) . . . . ? C2 C3 C4 C5 1.20(19) . . . . ? N4 C4 C5 C6 178.82(13) . . . . ? C3 C4 C5 C6 -0.68(19) . . . . ? C4 C5 C6 N1 -0.3(2) . . . . ? C3 C2 N1 C6 -0.2(2) . . . . ? C5 C6 N1 C2 0.8(2) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.44 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.354 _refine_diff_density_min -0.356 _refine_diff_density_rms 0.063 _database_code_depnum_ccdc_archive 'CCDC 959235' ####################################################################### # # 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_2012ln0017 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H16 N4 O5 S' _chemical_formula_weight 304.33 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 triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.4515(2) _cell_length_b 8.4229(2) _cell_length_c 12.4728(8) _cell_angle_alpha 96.429(7) _cell_angle_beta 97.523(7) _cell_angle_gamma 95.349(7) _cell_volume 663.70(5) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 5860 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 27.4 _exptl_crystal_description Needle _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.65 _exptl_crystal_size_mid 0.48 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.523 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 320 _exptl_absorpt_coefficient_mu 0.271 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.917 _exptl_absorpt_process_details ; CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 'Rigaku R-AXIS SPIDER IP' _diffrn_measurement_method 'profile data from oscillation \w-scans' _diffrn_detector_area_resol_mean 10 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6593 _diffrn_reflns_av_R_equivalents 0.0115 _diffrn_reflns_av_sigmaI/netI 0.0144 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.13 _diffrn_reflns_theta_max 27.45 _reflns_number_total 3023 _reflns_number_gt 2732 _reflns_threshold_expression >2\s(I) __computing_data_collection ; CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011) ; _computing_structure_solution 'Superflip (Palatinus & Chapuis, 2007)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997) ' _computing_molecular_graphics ; MERCURY (Bruno, Cole, Edgington, Kessler, Macrae, Pearson and Taylor, 2002) ; _computing_publication_material 'WINGX (Farrugia, 1998)' _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^ > 2\s(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^)+(0.0572P)^2^+0.3917P] 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 3023 _refine_ls_number_parameters 251 _refine_ls_number_restraints 328 _refine_ls_R_factor_all 0.0375 _refine_ls_R_factor_gt 0.0326 _refine_ls_wR_factor_ref 0.1134 _refine_ls_wR_factor_gt 0.1001 _refine_ls_goodness_of_fit_ref 1.192 _refine_ls_restrained_S_all 1.133 _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 C16 C 0.7970(2) 0.72189(19) 0.42902(12) 0.0190(3) Uani 1 1 d U . . H16 H 0.9399 0.7621 0.4534 0.023 Uiso 1 1 calc R . . C15 C 0.7415(2) 0.56004(18) 0.41001(12) 0.0168(3) Uani 1 1 d U . . H15 H 0.8452 0.4883 0.4214 0.020 Uiso 1 1 calc R . . C14 C 0.5279(2) 0.49865(18) 0.37299(11) 0.0146(3) Uani 1 1 d U . . C13 C 0.3796(2) 0.61277(18) 0.36086(12) 0.0172(3) Uani 1 1 d U . . H13 H 0.2346 0.5773 0.3389 0.021 Uiso 1 1 calc R . . C12 C 0.4464(3) 0.77285(19) 0.38089(13) 0.0206(3) Uani 1 1 d U . . H12 H 0.3470 0.8484 0.3716 0.025 Uiso 1 1 calc R . . N11 N 0.6518(2) 0.82623(16) 0.41379(11) 0.0210(3) Uani 1 1 d U . . H11 H 0.6914 0.9303 0.4254 0.025 Uiso 1 1 calc R . . N14 N 0.4687(2) 0.34142(15) 0.35029(11) 0.0184(3) Uani 1 1 d U . . H14A H 0.5625 0.2726 0.3581 0.022 Uiso 1 1 calc R . . H14B H 0.3357 0.3063 0.3275 0.022 Uiso 1 1 calc R . . O1 O 1.02885(18) 0.28480(13) 0.29246(10) 0.0227(3) Uani 1 1 d U . . O2 O 0.77170(19) 0.08131(15) 0.18891(10) 0.0288(3) Uani 1 1 d U . . O3 O 0.78982(18) 0.13029(13) 0.38458(10) 0.0221(3) Uani 1 1 d U . . O4 O 1.06566(19) 0.00426(14) 0.30586(11) 0.0268(3) Uani 1 1 d U . . S1 S 0.91694(5) 0.12522(4) 0.29279(3) 0.01561(12) Uani 1 1 d U . . C6' C 0.8219(12) 0.7018(7) 0.1411(6) 0.0227(12) Uani 0.581(5) 1 d PU A 1 H6' H 0.8572 0.7653 0.2101 0.027 Uiso 0.581(5) 1 calc PR A 1 C5' C 0.8112(11) 0.5412(7) 0.1354(5) 0.0194(12) Uani 0.581(5) 1 d PU A 1 H5' H 0.8372 0.4920 0.2000 0.023 Uiso 0.581(5) 1 calc PR A 1 C4' C 0.7603(4) 0.4436(4) 0.0314(3) 0.0141(7) Uani 0.581(5) 1 d PU A 1 C3' C 0.7306(17) 0.5253(8) -0.0602(8) 0.0165(13) Uani 0.581(5) 1 d PU A 1 H3' H 0.7043 0.4662 -0.1310 0.020 Uiso 0.581(5) 1 calc PR A 1 C2' C 0.7391(5) 0.6902(5) -0.0490(3) 0.0274(9) Uani 0.581(5) 1 d PU A 1 H2' H 0.7137 0.7447 -0.1113 0.033 Uiso 0.581(5) 1 calc PR A 1 N1' N 0.7842(4) 0.7739(5) 0.0521(3) 0.0286(8) Uani 0.581(5) 1 d PU A 1 H1' H 0.7887 0.8793 0.0591 0.034 Uiso 0.581(5) 1 calc PR A 1 N4' N 0.7463(4) 0.2834(4) 0.0228(2) 0.0200(7) Uani 0.581(5) 1 d PU A 1 H4'A H 0.7178 0.2261 -0.0419 0.024 Uiso 0.581(5) 1 calc PR A 1 H4'B H 0.7657 0.2351 0.0817 0.024 Uiso 0.581(5) 1 calc PR A 1 C2 C 0.8047(16) 0.4881(10) 0.1458(8) 0.0205(15) Uani 0.419(5) 1 d PU A 2 H2 H 0.8320 0.4578 0.2170 0.025 Uiso 0.419(5) 1 calc PR A 2 C3 C 0.8099(14) 0.6438(11) 0.1353(6) 0.0158(15) Uani 0.419(5) 1 d PU A 2 H3 H 0.8366 0.7221 0.1979 0.019 Uiso 0.419(5) 1 calc PR A 2 C4 C 0.7742(6) 0.6924(7) 0.0270(4) 0.0188(11) Uani 0.419(5) 1 d PU A 2 C6 C 0.7283(6) 0.4122(6) -0.0401(5) 0.0263(12) Uani 0.419(5) 1 d PU A 2 H6 H 0.7037 0.3292 -0.1000 0.032 Uiso 0.419(5) 1 calc PR A 2 N1 N 0.7629(5) 0.3719(6) 0.0610(5) 0.0259(10) Uani 0.419(5) 1 d PU A 2 H1 H 0.7583 0.2702 0.0716 0.031 Uiso 0.419(5) 1 calc PR A 2 N4 N 0.7833(6) 0.8472(6) 0.0147(3) 0.0228(10) Uani 0.419(5) 1 d PU A 2 H4A H 0.7590 0.8767 -0.0509 0.027 Uiso 0.419(5) 1 calc PR A 2 H4B H 0.8137 0.9205 0.0721 0.027 Uiso 0.419(5) 1 calc PR A 2 C5 C 0.727(3) 0.5705(11) -0.0608(11) 0.0160(17) Uani 0.419(5) 1 d PU A 2 H5 H 0.6944 0.5954 -0.1331 0.019 Uiso 0.419(5) 1 calc PR A 2 O1W O 0.3386(2) 0.96818(17) 0.15015(13) 0.0368(3) Uani 1 1 d D . . H2W H 0.264(3) 0.990(3) 0.1987(16) 0.055 Uiso 1 1 d D . . H1W H 0.4636(18) 1.002(3) 0.176(2) 0.055 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 C16 0.0177(7) 0.0213(7) 0.0173(7) 0.0014(6) 0.0041(5) -0.0029(6) C15 0.0151(7) 0.0194(7) 0.0164(6) 0.0032(5) 0.0029(5) 0.0020(5) C14 0.0158(7) 0.0175(7) 0.0111(6) 0.0027(5) 0.0035(5) 0.0014(5) C13 0.0148(6) 0.0186(7) 0.0185(7) 0.0035(5) 0.0025(5) 0.0018(5) C12 0.0232(8) 0.0186(7) 0.0223(7) 0.0066(6) 0.0064(6) 0.0063(6) N11 0.0258(7) 0.0151(6) 0.0225(6) 0.0029(5) 0.0072(5) -0.0009(5) N14 0.0154(6) 0.0146(6) 0.0245(6) 0.0005(5) 0.0020(5) 0.0009(5) O1 0.0194(5) 0.0143(5) 0.0340(6) 0.0051(5) 0.0042(5) -0.0032(4) O2 0.0208(6) 0.0299(7) 0.0305(6) -0.0069(5) -0.0058(5) 0.0021(5) O3 0.0209(5) 0.0158(5) 0.0321(6) 0.0063(4) 0.0090(5) 0.0029(4) O4 0.0216(6) 0.0212(6) 0.0419(7) 0.0101(5) 0.0082(5) 0.0112(5) S1 0.01127(18) 0.01061(19) 0.0244(2) 0.00210(13) 0.00090(14) 0.00099(12) C6' 0.0177(17) 0.016(3) 0.0331(19) -0.005(2) 0.0061(12) 0.000(2) C5' 0.0225(16) 0.011(3) 0.0232(19) -0.004(2) 0.0028(13) 0.003(3) C4' 0.0114(12) 0.0150(17) 0.0158(17) -0.0008(13) 0.0023(10) 0.0031(10) C3' 0.0156(16) 0.019(3) 0.0177(16) 0.004(3) 0.0046(11) 0.009(3) C2' 0.0181(14) 0.036(2) 0.034(2) 0.0193(14) 0.0088(12) 0.0074(12) N1' 0.0213(13) 0.0121(17) 0.055(2) 0.0059(17) 0.0129(12) 0.0028(12) N4' 0.0201(12) 0.0118(15) 0.0274(13) -0.0010(10) 0.0038(9) 0.0014(9) C2 0.015(2) 0.012(4) 0.037(3) 0.004(3) 0.0074(18) 0.005(3) C3 0.019(2) 0.014(4) 0.014(2) 0.005(3) 0.0012(16) 0.001(4) C4 0.0138(17) 0.015(2) 0.028(3) 0.0007(18) 0.0075(15) 0.0026(16) C6 0.0156(19) 0.019(3) 0.042(3) -0.008(2) 0.0076(17) 0.0002(15) N1 0.0148(16) 0.014(2) 0.052(3) 0.010(2) 0.0096(16) 0.0031(15) N4 0.0265(18) 0.021(2) 0.0198(17) -0.0003(14) 0.0029(13) 0.0033(14) C5 0.017(2) 0.013(4) 0.019(2) 0.002(3) 0.0030(16) 0.008(4) O1W 0.0215(6) 0.0270(7) 0.0616(10) 0.0014(6) 0.0097(6) 0.0006(5) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C16 N11 1.353(2) . ? C16 C15 1.363(2) . ? C16 H16 0.9500 . ? C15 C14 1.424(2) . ? C15 H15 0.9500 . ? C14 N14 1.3316(19) . ? C14 C13 1.424(2) . ? C13 C12 1.362(2) . ? C13 H13 0.9500 . ? C12 N11 1.353(2) . ? C12 H12 0.9500 . ? N11 H11 0.8800 . ? N14 H14A 0.8800 . ? N14 H14B 0.8800 . ? O1 S1 1.4659(11) . ? O2 S1 1.4844(12) . ? O3 S1 1.4923(12) . ? O4 S1 1.4709(11) . ? C6' N1' 1.329(9) . ? C6' C5' 1.341(5) . ? C6' H6' 0.9500 . ? C5' C4' 1.437(7) . ? C5' H5' 0.9500 . ? C4' N4' 1.335(4) . ? C4' C3' 1.400(9) . ? C3' C2' 1.375(6) . ? C3' H3' 0.9500 . ? C2' N1' 1.356(5) . ? C2' H2' 0.9500 . ? N1' H1' 0.8800 . ? N4' H4'A 0.8800 . ? N4' H4'B 0.8800 . ? C2 C3 1.330(7) . ? C2 N1 1.339(12) . ? C2 H2 0.9500 . ? C3 C4 1.451(8) . ? C3 H3 0.9500 . ? C4 N4 1.327(7) . ? C4 C5 1.396(13) . ? C6 N1 1.339(8) . ? C6 C5 1.387(8) . ? C6 H6 0.9500 . ? N1 H1 0.8800 . ? N4 H4A 0.8800 . ? N4 H4B 0.8800 . ? C5 H5 0.9500 . ? O1W H2W 0.839(9) . ? O1W H1W 0.839(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 N11 C16 C15 121.04(14) . . ? N11 C16 H16 119.5 . . ? C15 C16 H16 119.5 . . ? C16 C15 C14 119.89(14) . . ? C16 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? N14 C14 C15 121.65(13) . . ? N14 C14 C13 121.24(13) . . ? C15 C14 C13 117.12(13) . . ? C12 C13 C14 119.81(14) . . ? C12 C13 H13 120.1 . . ? C14 C13 H13 120.1 . . ? N11 C12 C13 121.16(14) . . ? N11 C12 H12 119.4 . . ? C13 C12 H12 119.4 . . ? C16 N11 C12 120.93(13) . . ? C16 N11 H11 119.5 . . ? C12 N11 H11 119.5 . . ? C14 N14 H14A 120.0 . . ? C14 N14 H14B 120.0 . . ? H14A N14 H14B 120.0 . . ? O1 S1 O4 110.89(7) . . ? O1 S1 O2 109.02(7) . . ? O4 S1 O2 110.02(7) . . ? O1 S1 O3 109.23(7) . . ? O4 S1 O3 109.20(7) . . ? O2 S1 O3 108.43(7) . . ? N1' C6' C5' 121.4(5) . . ? N1' C6' H6' 119.3 . . ? C5' C6' H6' 119.3 . . ? C6' C5' C4' 120.0(5) . . ? C6' C5' H5' 120.0 . . ? C4' C5' H5' 120.0 . . ? N4' C4' C3' 121.9(4) . . ? N4' C4' C5' 121.6(4) . . ? C3' C4' C5' 116.5(5) . . ? C2' C3' C4' 120.8(7) . . ? C2' C3' H3' 119.6 . . ? C4' C3' H3' 119.6 . . ? N1' C2' C3' 119.2(5) . . ? N1' C2' H2' 120.4 . . ? C3' C2' H2' 120.4 . . ? C6' N1' C2' 122.1(4) . . ? C6' N1' H1' 118.9 . . ? C2' N1' H1' 118.9 . . ? C4' N4' H4'A 120.0 . . ? C4' N4' H4'B 120.0 . . ? H4'A N4' H4'B 120.0 . . ? C3 C2 N1 123.3(8) . . ? C3 C2 H2 118.4 . . ? N1 C2 H2 118.4 . . ? C2 C3 C4 119.1(7) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? N4 C4 C5 122.8(6) . . ? N4 C4 C3 120.0(5) . . ? C5 C4 C3 117.2(7) . . ? N1 C6 C5 122.5(8) . . ? N1 C6 H6 118.8 . . ? C5 C6 H6 118.8 . . ? C6 N1 C2 119.3(6) . . ? C6 N1 H1 120.4 . . ? C2 N1 H1 120.4 . . ? C4 N4 H4A 120.0 . . ? C4 N4 H4B 120.0 . . ? H4A N4 H4B 120.0 . . ? C6 C5 C4 118.6(10) . . ? C6 C5 H5 120.7 . . ? C4 C5 H5 120.7 . . ? H2W O1W H1W 107.8(19) . . ? 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 N11 C16 C15 C14 0.3(2) . . . . ? C16 C15 C14 N14 177.89(14) . . . . ? C16 C15 C14 C13 -1.9(2) . . . . ? N14 C14 C13 C12 -177.59(14) . . . . ? C15 C14 C13 C12 2.2(2) . . . . ? C14 C13 C12 N11 -0.9(2) . . . . ? C15 C16 N11 C12 1.1(2) . . . . ? C13 C12 N11 C16 -0.8(2) . . . . ? N1' C6' C5' C4' 0.7(8) . . . . ? C6' C5' C4' N4' -179.4(4) . . . . ? C6' C5' C4' C3' 1.9(8) . . . . ? N4' C4' C3' C2' 177.9(6) . . . . ? C5' C4' C3' C2' -3.4(11) . . . . ? C4' C3' C2' N1' 2.3(11) . . . . ? C5' C6' N1' C2' -2.0(8) . . . . ? C3' C2' N1' C6' 0.4(8) . . . . ? N1 C2 C3 C4 -1.7(11) . . . . ? C2 C3 C4 N4 -178.5(6) . . . . ? C2 C3 C4 C5 2.7(11) . . . . ? C5 C6 N1 C2 -2.2(11) . . . . ? C3 C2 N1 C6 1.4(10) . . . . ? N1 C6 C5 C4 3.4(16) . . . . ? N4 C4 C5 C6 177.8(8) . . . . ? C3 C4 C5 C6 -3.5(16) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.590 _refine_diff_density_min -0.460 _refine_diff_density_rms 0.091 _database_code_depnum_ccdc_archive 'CCDC 959236' ####################################################################### # # 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_2012ln0043a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H8 N4 O3' _chemical_formula_weight 172.15 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 P21/n _symmetry_space_group_name_Hall '-P 2yn' 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 7.0735(5) _cell_length_b 11.0546(8) _cell_length_c 9.4018(6) _cell_angle_alpha 90.00 _cell_angle_beta 92.308(7) _cell_angle_gamma 90.00 _cell_volume 734.57(9) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 6827 _cell_measurement_theta_min 3.4 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.557 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 360 _exptl_absorpt_coefficient_mu 0.130 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.832 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ; CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator Confocal _diffrn_measurement_device_type ; Rigaku Saturn724+ (2x2 bin mode) ; _diffrn_measurement_method 'profile data from \w-scans' _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7979 _diffrn_reflns_av_R_equivalents 0.0442 _diffrn_reflns_av_sigmaI/netI 0.0312 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 3.42 _diffrn_reflns_theta_max 27.46 _reflns_number_total 1680 _reflns_number_gt 1415 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011) ; _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; MERCURY (Bruno, Cole, Edgington, Kessler, Macrae, McCabe, Pearson and Taylor, 2002) ; _computing_publication_material 'WINGX (Farrugia, 1998)' _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^ > 2\s(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^)+(0.0412P)^2^+0.1831P] 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 1680 _refine_ls_number_parameters 133 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0409 _refine_ls_R_factor_gt 0.0338 _refine_ls_wR_factor_ref 0.0884 _refine_ls_wR_factor_gt 0.0853 _refine_ls_goodness_of_fit_ref 1.098 _refine_ls_restrained_S_all 1.098 _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 C2 C 0.03506(17) 0.23602(11) 0.66491(13) 0.0152(3) Uani 1 1 d . . . C3 C 0.04174(17) 0.25106(11) 0.81006(13) 0.0136(3) Uani 1 1 d . . . C4 C 0.11453(16) 0.36252(11) 0.86709(13) 0.0135(3) Uani 1 1 d . . . C5 C 0.16846(18) 0.45202(11) 0.77001(13) 0.0160(3) Uani 1 1 d . . . C6 C 0.15605(18) 0.43081(12) 0.62625(14) 0.0173(3) Uani 1 1 d . . . N1 N 0.09053(15) 0.32429(10) 0.57652(11) 0.0168(2) Uani 1 1 d . . . N3 N 0.12885(16) 0.38016(10) 1.00836(11) 0.0162(2) Uani 1 1 d . . . N4 N -0.02647(16) 0.16399(10) 0.90009(12) 0.0167(2) Uani 1 1 d . . . H2 H -0.010(2) 0.1640(14) 0.6204(16) 0.020 Uiso 1 1 d . . . H5 H 0.210(2) 0.5310(14) 0.8032(15) 0.020 Uiso 1 1 d . . . H6 H 0.193(2) 0.4876(14) 0.5561(16) 0.020 Uiso 1 1 d . . . H1 H 0.092(2) 0.3051(14) 0.4870(17) 0.020 Uiso 1 1 d . . . H3A H 0.185(2) 0.4470(14) 1.0391(16) 0.020 Uiso 1 1 d . . . H3B H 0.096(2) 0.3273(15) 1.0679(16) 0.020 Uiso 1 1 d . . . H4A H -0.056(2) 0.0955(14) 0.8559(16) 0.020 Uiso 1 1 d . . . H4B H 0.028(2) 0.1550(14) 0.9864(18) 0.020 Uiso 1 1 d . . . N5 N 0.11438(14) 0.14051(9) 0.28294(10) 0.0143(2) Uani 1 1 d . . . O5A O 0.05448(13) 0.24788(7) 0.27695(9) 0.0184(2) Uani 1 1 d . . . O5B O 0.12978(14) 0.08750(8) 0.39973(9) 0.0225(2) Uani 1 1 d . . . O5C O 0.15752(13) 0.08725(8) 0.17054(9) 0.0187(2) 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 C2 0.0127(6) 0.0160(6) 0.0167(6) -0.0019(5) 0.0001(5) 0.0001(5) C3 0.0102(6) 0.0154(6) 0.0152(6) 0.0001(4) 0.0005(4) 0.0010(4) C4 0.0096(6) 0.0155(6) 0.0154(6) -0.0014(5) -0.0002(4) 0.0028(4) C5 0.0148(6) 0.0140(6) 0.0192(6) -0.0001(5) 0.0009(5) 0.0004(5) C6 0.0153(6) 0.0170(6) 0.0197(6) 0.0031(5) 0.0032(5) 0.0017(5) N1 0.0170(6) 0.0210(6) 0.0124(5) 0.0000(4) 0.0013(4) 0.0017(4) N3 0.0213(6) 0.0130(5) 0.0144(5) -0.0008(4) -0.0006(4) -0.0016(4) N4 0.0208(6) 0.0146(5) 0.0146(5) 0.0003(4) 0.0003(4) -0.0037(4) N5 0.0137(5) 0.0141(5) 0.0149(5) 0.0002(4) -0.0006(4) -0.0018(4) O5A 0.0231(5) 0.0136(4) 0.0185(5) 0.0016(3) -0.0007(4) 0.0027(4) O5B 0.0320(6) 0.0215(5) 0.0141(4) 0.0052(4) 0.0023(4) 0.0066(4) O5C 0.0230(5) 0.0184(5) 0.0149(4) -0.0042(3) 0.0023(4) -0.0022(4) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C2 N1 1.3501(16) . ? C2 C3 1.3737(17) . ? C2 H2 0.948(16) . ? C3 N4 1.3815(16) . ? C3 C4 1.4312(16) . ? C4 N3 1.3422(16) . ? C4 C5 1.4091(17) . ? C5 C6 1.3712(18) . ? C5 H5 0.968(16) . ? C6 N1 1.3426(17) . ? C6 H6 0.955(16) . ? N1 H1 0.868(16) . ? N3 H3A 0.881(16) . ? N3 H3B 0.849(16) . ? N4 H4A 0.885(16) . ? N4 H4B 0.891(17) . ? N5 O5B 1.2455(13) . ? N5 O5C 1.2579(13) . ? N5 O5A 1.2608(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 N1 C2 C3 121.65(11) . . ? N1 C2 H2 115.8(9) . . ? C3 C2 H2 122.5(9) . . ? C2 C3 N4 121.70(11) . . ? C2 C3 C4 118.28(11) . . ? N4 C3 C4 119.97(11) . . ? N3 C4 C5 121.82(11) . . ? N3 C4 C3 120.50(11) . . ? C5 C4 C3 117.68(11) . . ? C6 C5 C4 120.68(11) . . ? C6 C5 H5 118.6(8) . . ? C4 C5 H5 120.7(8) . . ? N1 C6 C5 120.05(12) . . ? N1 C6 H6 115.9(9) . . ? C5 C6 H6 124.0(9) . . ? C6 N1 C2 121.62(11) . . ? C6 N1 H1 122.3(10) . . ? C2 N1 H1 115.8(10) . . ? C4 N3 H3A 117.5(10) . . ? C4 N3 H3B 122.7(10) . . ? H3A N3 H3B 119.6(14) . . ? C3 N4 H4A 113.0(10) . . ? C3 N4 H4B 119.1(10) . . ? H4A N4 H4B 114.8(14) . . ? O5B N5 O5C 120.32(10) . . ? O5B N5 O5A 119.98(10) . . ? O5C N5 O5A 119.70(10) . . ? 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 N1 C2 C3 N4 175.69(11) . . . . ? N1 C2 C3 C4 -1.69(18) . . . . ? C2 C3 C4 N3 -178.12(11) . . . . ? N4 C3 C4 N3 4.45(18) . . . . ? C2 C3 C4 C5 2.32(17) . . . . ? N4 C3 C4 C5 -175.10(11) . . . . ? N3 C4 C5 C6 178.66(12) . . . . ? C3 C4 C5 C6 -1.79(18) . . . . ? C4 C5 C6 N1 0.55(19) . . . . ? C5 C6 N1 C2 0.19(19) . . . . ? C3 C2 N1 C6 0.42(19) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.275 _refine_diff_density_min -0.231 _refine_diff_density_rms 0.047 _database_code_depnum_ccdc_archive 'CCDC 959237' ####################################################################### # # 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_2012ln0045 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H11 N5 O7' _chemical_formula_weight 253.19 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 _symmetry_space_group_name_Hall '-P 2ac 2ab' 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 17.0057(11) _cell_length_b 12.7153(4) _cell_length_c 9.1321(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1974.66(16) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 19573 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.703 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1056 _exptl_absorpt_coefficient_mu 0.158 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.898 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ; CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator Confocal _diffrn_measurement_device_type ; Rigaku Saturn724+ (2x2 bin mode) ; _diffrn_measurement_method 'profile data from \w-scans' _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21219 _diffrn_reflns_av_R_equivalents 0.0320 _diffrn_reflns_av_sigmaI/netI 0.0174 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2254 _reflns_number_gt 2106 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011) ; _computing_structure_solution 'SUPERFLIP (Palatinus & Chapuis, 2007)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; MERCURY (Bruno, Cole, Edgington, Kessler, Macrae, McCabe, Pearson and Taylor, 2002) ; _computing_publication_material 'WINGX (Farrugia, 1998)' _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^ > 2\s(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^)+(0.0338P)^2^+1.0497P] 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 2254 _refine_ls_number_parameters 161 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0301 _refine_ls_R_factor_gt 0.0283 _refine_ls_wR_factor_ref 0.0757 _refine_ls_wR_factor_gt 0.0747 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _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 C2 C 0.92686(6) 0.11457(8) 0.23460(12) 0.0124(2) Uani 1 1 d . . . H2 H 0.8872 0.1098 0.3076 0.015 Uiso 1 1 calc R . . C3 C 0.90608(6) 0.12932(8) 0.09118(11) 0.0105(2) Uani 1 1 d . . . C4 C 0.96415(6) 0.13430(8) -0.02001(12) 0.0112(2) Uani 1 1 d . . . C5 C 1.04370(6) 0.12763(8) 0.02726(12) 0.0122(2) Uani 1 1 d . . . H5 H 1.0851 0.1329 -0.0421 0.015 Uiso 1 1 calc R . . C6 C 1.06064(6) 0.11375(8) 0.17173(12) 0.0132(2) Uani 1 1 d . . . H6 H 1.1140 0.1089 0.2018 0.016 Uiso 1 1 calc R . . N1 N 1.00312(5) 0.10680(7) 0.27287(10) 0.01260(19) Uani 1 1 d . . . H1 H 1.0156 0.0970 0.3654 0.015 Uiso 1 1 calc R . . N3 N 0.82275(5) 0.13763(7) 0.05497(10) 0.01090(19) Uani 1 1 d . . . H3A H 0.8038 0.0730 0.0310 0.016 Uiso 1 1 calc R . . H3B H 0.8165 0.1820 -0.0223 0.016 Uiso 1 1 calc R . . H3C H 0.7960 0.1631 0.1336 0.016 Uiso 1 1 calc R . . N4 N 0.94627(5) 0.14394(8) -0.16127(10) 0.0144(2) Uani 1 1 d . . . H4A H 0.8968 0.1475 -0.1888 0.017 Uiso 1 1 calc R . . H4B H 0.9840 0.1468 -0.2272 0.017 Uiso 1 1 calc R . . N10 N 0.79046(5) 0.42426(7) 0.10815(10) 0.01283(19) Uani 1 1 d . . . N20 N 0.10735(5) 0.36336(7) 0.08520(10) 0.01196(19) Uani 1 1 d . . . O1 O 0.78434(5) 0.46949(7) 0.22778(9) 0.01822(18) Uani 1 1 d . . . O2 O 0.84787(5) 0.36635(7) 0.07950(9) 0.01858(19) Uani 1 1 d . . . O1W O 0.26585(4) 0.22533(6) 0.18634(9) 0.01384(17) Uani 1 1 d D . . O3 O 0.73728(5) 0.43664(6) 0.01086(9) 0.01624(18) Uani 1 1 d . . . O4 O 0.12901(5) 0.33697(7) 0.21131(8) 0.01666(18) Uani 1 1 d . . . O5 O 0.15141(5) 0.35334(7) -0.02223(9) 0.01808(19) Uani 1 1 d . . . O6 O 0.03856(5) 0.39964(7) 0.06932(9) 0.01778(18) Uani 1 1 d . . . H1W H 0.2574(10) 0.1767(10) 0.1272(15) 0.027 Uiso 1 1 d D . . H2W H 0.2233(7) 0.2586(12) 0.1947(18) 0.027 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 C2 0.0127(5) 0.0106(5) 0.0139(5) -0.0006(4) 0.0005(4) 0.0006(4) C3 0.0093(4) 0.0088(5) 0.0135(5) -0.0007(4) 0.0001(4) 0.0000(3) C4 0.0134(5) 0.0079(5) 0.0121(5) -0.0006(4) 0.0007(4) -0.0005(4) C5 0.0119(5) 0.0113(5) 0.0133(5) -0.0003(4) 0.0013(4) -0.0005(4) C6 0.0119(5) 0.0113(5) 0.0164(5) -0.0004(4) -0.0005(4) 0.0002(4) N1 0.0146(4) 0.0131(5) 0.0100(4) 0.0006(3) -0.0023(3) 0.0009(3) N3 0.0100(4) 0.0117(4) 0.0111(4) 0.0004(3) -0.0005(3) -0.0003(3) N4 0.0134(4) 0.0185(5) 0.0112(4) 0.0009(4) 0.0010(3) 0.0002(3) N10 0.0156(4) 0.0113(4) 0.0116(4) 0.0019(3) -0.0012(3) -0.0021(3) N20 0.0123(4) 0.0122(4) 0.0113(4) -0.0014(3) 0.0004(3) -0.0008(3) O1 0.0244(4) 0.0196(4) 0.0107(4) -0.0031(3) 0.0001(3) -0.0041(3) O2 0.0167(4) 0.0180(4) 0.0210(4) -0.0016(3) -0.0040(3) 0.0049(3) O1W 0.0128(4) 0.0148(4) 0.0139(4) -0.0024(3) -0.0014(3) 0.0021(3) O3 0.0173(4) 0.0169(4) 0.0145(4) -0.0018(3) -0.0061(3) 0.0035(3) O4 0.0170(4) 0.0235(4) 0.0095(4) 0.0006(3) -0.0016(3) 0.0031(3) O5 0.0147(4) 0.0274(5) 0.0121(4) 0.0015(3) 0.0045(3) 0.0011(3) O6 0.0129(4) 0.0251(4) 0.0153(4) -0.0013(3) -0.0011(3) 0.0074(3) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C2 N1 1.3467(14) . ? C2 C3 1.3695(15) . ? C2 H2 0.9500 . ? C3 C4 1.4178(14) . ? C3 N3 1.4590(13) . ? C4 N4 1.3310(14) . ? C4 C5 1.4226(14) . ? C5 C6 1.3618(16) . ? C5 H5 0.9500 . ? C6 N1 1.3482(14) . ? C6 H6 0.9500 . ? N1 H1 0.8800 . ? N3 H3A 0.9100 . ? N3 H3B 0.9100 . ? N3 H3C 0.9100 . ? N4 H4A 0.8800 . ? N4 H4B 0.8800 . ? N10 O1 1.2389(12) . ? N10 O2 1.2507(12) . ? N10 O3 1.2775(12) . ? N20 O5 1.2410(12) . ? N20 O4 1.2549(12) . ? N20 O6 1.2659(12) . ? O1W H1W 0.833(9) . ? O1W H2W 0.842(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 N1 C2 C3 120.45(10) . . ? N1 C2 H2 119.8 . . ? C3 C2 H2 119.8 . . ? C2 C3 C4 120.75(9) . . ? C2 C3 N3 118.51(9) . . ? C4 C3 N3 120.73(9) . . ? N4 C4 C3 122.62(10) . . ? N4 C4 C5 121.12(10) . . ? C3 C4 C5 116.26(10) . . ? C6 C5 C4 120.18(10) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? N1 C6 C5 121.25(10) . . ? N1 C6 H6 119.4 . . ? C5 C6 H6 119.4 . . ? C2 N1 C6 121.06(9) . . ? C2 N1 H1 119.5 . . ? C6 N1 H1 119.5 . . ? C3 N3 H3A 109.5 . . ? C3 N3 H3B 109.5 . . ? H3A N3 H3B 109.5 . . ? C3 N3 H3C 109.5 . . ? H3A N3 H3C 109.5 . . ? H3B N3 H3C 109.5 . . ? C4 N4 H4A 120.0 . . ? C4 N4 H4B 120.0 . . ? H4A N4 H4B 120.0 . . ? O1 N10 O2 121.56(9) . . ? O1 N10 O3 119.78(9) . . ? O2 N10 O3 118.67(9) . . ? O5 N20 O4 121.39(9) . . ? O5 N20 O6 120.32(9) . . ? O4 N20 O6 118.28(9) . . ? H1W O1W H2W 106.4(16) . . ? 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 N1 C2 C3 C4 1.44(16) . . . . ? N1 C2 C3 N3 -179.80(9) . . . . ? C2 C3 C4 N4 177.00(10) . . . . ? N3 C3 C4 N4 -1.74(16) . . . . ? C2 C3 C4 C5 -2.55(15) . . . . ? N3 C3 C4 C5 178.71(9) . . . . ? N4 C4 C5 C6 -177.48(10) . . . . ? C3 C4 C5 C6 2.07(15) . . . . ? C4 C5 C6 N1 -0.48(16) . . . . ? C3 C2 N1 C6 0.29(16) . . . . ? C5 C6 N1 C2 -0.77(16) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.367 _refine_diff_density_min -0.261 _refine_diff_density_rms 0.044 _database_code_depnum_ccdc_archive 'CCDC 959238' ####################################################################### # # 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_2008rm0007c _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common bis(3,4-diaminopyridinium)_sulfate_dihydrate _chemical_melting_point ? _chemical_formula_moiety '2(C5 H8 N3), O4 S, 2(H2 O)' _chemical_formula_sum 'C10 H20 N6 O6 S' _chemical_formula_weight 352.38 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 tetragonal _symmetry_space_group_name_H-M I41/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-y+3/4, x+1/4, z+1/4' 'y+3/4, -x+3/4, z+3/4' 'x+1/2, y+1/2, z+1/2' '-x+1, -y+1/2, z+1' '-y+5/4, x+3/4, z+3/4' 'y+5/4, -x+5/4, z+5/4' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'y-3/4, -x-1/4, -z-1/4' '-y-3/4, x-3/4, -z-3/4' '-x+1/2, -y+1/2, -z+1/2' 'x, y+1/2, -z' 'y-1/4, -x+1/4, -z+1/4' '-y-1/4, x-1/4, -z-1/4' _cell_length_a 15.2902(10) _cell_length_b 15.2902(10) _cell_length_c 13.2563(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3099.2(3) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 15257 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Lath _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.510 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1488 _exptl_absorpt_coefficient_mu 0.251 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8912 _exptl_absorpt_correction_T_max 0.9900 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius Roper CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15657 _diffrn_reflns_av_R_equivalents 0.1342 _diffrn_reflns_av_sigmaI/netI 0.0846 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.35 _diffrn_reflns_theta_max 27.48 _reflns_number_total 1716 _reflns_number_gt 1017 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^)+(0.0936P)^2^+0.0922P] 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 1716 _refine_ls_number_parameters 112 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1177 _refine_ls_R_factor_gt 0.0622 _refine_ls_wR_factor_ref 0.1768 _refine_ls_wR_factor_gt 0.1540 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _refine_ls_shift/su_max 0.015 _refine_ls_shift/su_mean 0.001 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 H10A H 0.061(3) 0.319(3) 0.427(3) 0.053(13) Uiso 1 1 d . . . H10B H 0.083(4) 0.307(3) 0.326(4) 0.070(16) Uiso 1 1 d . . . O1 O 0.55260(17) 0.69209(16) 0.56028(17) 0.0386(7) Uani 1 1 d . . . S1 S 0.5000 0.7500 0.6250 0.0228(4) Uani 1 4 d S . . O2 O -0.00802(15) 0.32862(14) 0.56049(16) 0.0287(6) Uani 1 1 d . . . O10 O 0.10443(18) 0.30679(19) 0.3892(2) 0.0424(7) Uani 1 1 d . . . S2 S 0.0000 0.2500 0.6250 0.0236(4) Uani 1 4 d S . . C2 C 0.8147(3) 0.4806(2) 0.5705(3) 0.0374(9) Uani 1 1 d . . . H2 H 0.8658 0.5159 0.5679 0.045 Uiso 1 1 calc R . . C3 C 0.7323(2) 0.5205(2) 0.5702(2) 0.0294(8) Uani 1 1 d . . . C4 C 0.6571(2) 0.4666(2) 0.5752(3) 0.0335(8) Uani 1 1 d . . . C5 C 0.6715(3) 0.3740(3) 0.5765(3) 0.0406(9) Uani 1 1 d . . . H5 H 0.6230 0.3352 0.5769 0.049 Uiso 1 1 calc R . . C6 C 0.7531(2) 0.3418(3) 0.5772(3) 0.0401(9) Uani 1 1 d . . . H6 H 0.7612 0.2803 0.5799 0.048 Uiso 1 1 calc R . . N1 N 0.8228(2) 0.3933(2) 0.5743(2) 0.0432(8) Uani 1 1 d . . . H1A H 0.8753 0.3698 0.5750 0.052 Uiso 1 1 calc R . . N2 N 0.72712(19) 0.61001(19) 0.5633(2) 0.0344(8) Uani 1 1 d . . . H2A H 0.7752 0.6414 0.5591 0.041 Uiso 1 1 calc R . . H2B H 0.6757 0.6359 0.5630 0.041 Uiso 1 1 calc R . . N3 N 0.5785(2) 0.4996(2) 0.5762(2) 0.0414(8) Uani 1 1 d . . . H3B H 0.5713 0.5567 0.5737 0.050 Uiso 1 1 calc R . . H3C H 0.5327 0.4649 0.5793 0.050 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 0.0401(15) 0.0348(14) 0.0408(14) -0.0030(11) 0.0030(11) 0.0180(12) S1 0.0186(5) 0.0186(5) 0.0312(8) 0.000 0.000 0.000 O2 0.0254(12) 0.0222(12) 0.0385(13) 0.0024(9) 0.0000(10) 0.0050(9) O10 0.0289(14) 0.0559(18) 0.0424(17) 0.0012(13) 0.0030(13) -0.0069(13) S2 0.0192(5) 0.0192(5) 0.0322(8) 0.000 0.000 0.000 C2 0.056(3) 0.030(2) 0.0261(19) -0.0018(14) -0.0049(16) 0.0120(18) C3 0.0342(18) 0.0302(18) 0.0237(16) -0.0011(14) -0.0041(15) 0.0047(15) C4 0.037(2) 0.034(2) 0.0303(18) -0.0006(15) -0.0064(16) 0.0037(16) C5 0.044(2) 0.040(2) 0.0381(19) -0.0024(17) -0.0060(18) -0.0018(18) C6 0.035(2) 0.042(2) 0.043(2) -0.0022(17) -0.0017(17) 0.0030(18) N1 0.0360(18) 0.046(2) 0.0474(19) 0.0017(15) -0.0014(15) 0.0141(15) N2 0.0266(15) 0.0262(15) 0.0504(19) -0.0009(13) -0.0023(13) -0.0001(12) N3 0.0349(17) 0.0339(18) 0.055(2) -0.0029(15) 0.0002(15) 0.0017(14) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 S1 1.472(2) . ? S1 O1 1.472(2) 6_564 ? S1 O1 1.472(2) 15_566 ? S1 O1 1.472(2) 12_767 ? O2 S2 1.480(2) . ? O10 H10A 0.85(5) . ? O10 H10B 0.90(5) . ? S2 O2 1.480(2) 12_667 ? S2 O2 1.480(2) 6_454 ? S2 O2 1.480(2) 15_556 ? C2 N1 1.341(5) . ? C2 C3 1.400(5) . ? C2 H2 0.9500 . ? C3 N2 1.374(4) . ? C3 C4 1.417(5) . ? C4 N3 1.304(4) . ? C4 C5 1.432(6) . ? C5 C6 1.342(6) . ? C5 H5 0.9500 . ? C6 N1 1.325(5) . ? C6 H6 0.9500 . ? N1 H1A 0.8800 . ? N2 H2A 0.8800 . ? N2 H2B 0.8800 . ? N3 H3B 0.8800 . ? N3 H3C 0.8800 . ? 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 O1 S1 O1 109.86(9) 6_564 15_566 ? O1 S1 O1 108.70(18) 6_564 . ? O1 S1 O1 109.86(9) 15_566 . ? O1 S1 O1 109.86(9) 6_564 12_767 ? O1 S1 O1 108.70(18) 15_566 12_767 ? O1 S1 O1 109.86(9) . 12_767 ? H10A O10 H10B 106(5) . . ? O2 S2 O2 109.49(8) 12_667 6_454 ? O2 S2 O2 109.49(8) 12_667 . ? O2 S2 O2 109.43(17) 6_454 . ? O2 S2 O2 109.43(17) 12_667 15_556 ? O2 S2 O2 109.49(8) 6_454 15_556 ? O2 S2 O2 109.49(8) . 15_556 ? N1 C2 C3 121.1(4) . . ? N1 C2 H2 119.4 . . ? C3 C2 H2 119.4 . . ? N2 C3 C2 119.1(3) . . ? N2 C3 C4 122.4(3) . . ? C2 C3 C4 118.4(3) . . ? N3 C4 C3 121.5(3) . . ? N3 C4 C5 121.6(3) . . ? C3 C4 C5 116.8(3) . . ? C6 C5 C4 120.4(4) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? N1 C6 C5 122.0(4) . . ? N1 C6 H6 119.0 . . ? C5 C6 H6 119.0 . . ? C6 N1 C2 121.2(3) . . ? C6 N1 H1A 119.4 . . ? C2 N1 H1A 119.4 . . ? C3 N2 H2A 120.0 . . ? C3 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? C4 N3 H3B 120.0 . . ? C4 N3 H3C 120.0 . . ? H3B N3 H3C 120.0 . . ? 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 O10 H10B O1 0.90(5) 1.85(6) 2.739(4) 171(5) 16_656 N1 H1A O2 0.88 1.90 2.776(4) 172.1 1_655 N1 H1A O2 0.88 2.57 3.155(4) 124.5 12_767 N1 H1A S2 0.88 2.73 3.549(3) 156.3 1_655 N2 H2A O10 0.88 2.12 2.941(4) 155.5 9_666 N3 H3C O10 0.88 2.31 3.147(5) 158.0 3 N2 H2B O1 0.88 2.07 2.949(4) 177.7 . N3 H3B O1 0.88 2.10 2.977(4) 177.2 . _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.958 _refine_diff_density_max 0.534 _refine_diff_density_min -0.340 _refine_diff_density_rms 0.073 _database_code_depnum_ccdc_archive 'CCDC 959239' ####################################################################### # # 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_2008rm0005 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 3,4-diaminopyridinium_sulfate_dihydrate _chemical_melting_point ? _chemical_formula_moiety 'C5 H9 N3, O4 S, 2(H2 O)' _chemical_formula_sum 'C5 H13 N3 O6 S' _chemical_formula_weight 243.24 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 triclinic _symmetry_space_group_name_H-M p-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.9429(3) _cell_length_b 10.2338(5) _cell_length_c 14.5568(8) _cell_angle_alpha 103.319(2) _cell_angle_beta 100.970(3) _cell_angle_gamma 92.592(3) _cell_volume 983.78(8) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 10741 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.642 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 0.346 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9662 _exptl_absorpt_correction_T_max 0.9965 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius Roper CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17819 _diffrn_reflns_av_R_equivalents 0.0878 _diffrn_reflns_av_sigmaI/netI 0.0926 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4492 _reflns_number_gt 2962 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^)+(0.0627P)^2^+0.1107P] 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 4492 _refine_ls_number_parameters 332 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0981 _refine_ls_R_factor_gt 0.0545 _refine_ls_wR_factor_ref 0.1381 _refine_ls_wR_factor_gt 0.1187 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.053 _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 N11 N 0.2850(4) 0.8509(3) 0.2734(2) 0.0226(6) Uani 1 1 d . . . N12 N 0.2383(4) 0.6963(3) 0.0145(2) 0.0175(6) Uani 1 1 d . . . N13 N 0.2681(4) 0.9773(3) 0.0249(2) 0.0201(6) Uani 1 1 d . . . C12 C 0.2661(4) 0.7577(3) 0.1899(2) 0.0197(7) Uani 1 1 d . . . H12 H 0.2601 0.6646 0.1894 0.024 Uiso 1 1 calc R . . C13 C 0.2556(4) 0.7968(3) 0.1059(2) 0.0149(6) Uani 1 1 d . . . C14 C 0.2680(4) 0.9351(3) 0.1047(2) 0.0167(7) Uani 1 1 d . . . C15 C 0.2862(4) 1.0280(3) 0.1954(2) 0.0192(7) Uani 1 1 d . . . H15 H 0.2918 1.1220 0.1991 0.023 Uiso 1 1 calc R . . C16 C 0.2956(4) 0.9838(3) 0.2766(2) 0.0227(7) Uani 1 1 d . . . H16 H 0.3100 1.0474 0.3369 0.027 Uiso 1 1 calc R . . N21 N 0.7713(4) 0.7134(3) 0.1907(2) 0.0207(6) Uani 1 1 d . . . N22 N 0.7940(4) 0.6047(3) 0.41532(19) 0.0150(5) Uani 1 1 d . . . N23 N 0.7998(4) 0.8948(3) 0.4754(2) 0.0209(6) Uani 1 1 d . . . C22 C 0.7800(4) 0.6358(3) 0.2540(2) 0.0187(7) Uani 1 1 d . . . H22 H 0.7816 0.5409 0.2324 0.022 Uiso 1 1 calc R . . C23 C 0.7865(4) 0.6931(3) 0.3502(2) 0.0143(6) Uani 1 1 d . . . C24 C 0.7879(4) 0.8341(3) 0.3839(2) 0.0178(7) Uani 1 1 d . . . C25 C 0.7751(4) 0.9102(3) 0.3125(2) 0.0206(7) Uani 1 1 d . . . H25 H 0.7725 1.0053 0.3306 0.025 Uiso 1 1 calc R . . C26 C 0.7669(4) 0.8475(3) 0.2195(2) 0.0182(7) Uani 1 1 d . . . H26 H 0.7577 0.8996 0.1729 0.022 Uiso 1 1 calc R . . S1 S 0.27790(10) 0.35530(7) 0.06411(5) 0.01368(19) Uani 1 1 d . . . O11 O 0.1208(3) 0.2890(2) 0.09819(14) 0.0175(5) Uani 1 1 d . . . O12 O 0.1858(3) 0.4200(2) -0.01270(15) 0.0168(5) Uani 1 1 d . . . O13 O 0.3983(3) 0.2503(2) 0.02274(16) 0.0205(5) Uani 1 1 d . . . O14 O 0.3986(3) 0.4586(2) 0.14363(15) 0.0214(5) Uani 1 1 d . . . S2 S 0.65827(10) 0.30147(7) 0.52640(6) 0.0167(2) Uani 1 1 d . . . O21 O 0.8152(3) 0.3773(2) 0.49912(15) 0.0192(5) Uani 1 1 d . . . O22 O 0.4695(3) 0.3021(2) 0.45943(15) 0.0215(5) Uani 1 1 d . . . O23 O 0.6387(3) 0.3651(3) 0.62525(15) 0.0276(6) Uani 1 1 d . . . O24 O 0.7094(4) 0.1635(2) 0.5258(2) 0.0449(8) Uani 1 1 d . . . O1 O 0.5794(3) 0.3578(2) 0.29624(16) 0.0192(5) Uani 1 1 d D . . O2 O 0.0858(3) 0.4224(2) 0.28544(17) 0.0263(5) Uani 1 1 d D . . O3 O 0.7536(3) 0.1585(2) 0.17231(16) 0.0264(5) Uani 1 1 d D . . O4 O 1.0180(3) 0.2189(2) 0.36650(17) 0.0232(5) Uani 1 1 d D . . H13A H 0.252(5) 0.918(4) -0.028(3) 0.028 Uiso 1 1 d . . . H12A H 0.343(5) 0.706(3) -0.009(2) 0.028 Uiso 1 1 d . . . H22C H 0.721(5) 0.637(4) 0.454(3) 0.028 Uiso 1 1 d . . . H23B H 0.817(5) 0.848(4) 0.519(3) 0.028 Uiso 1 1 d . . . H22B H 0.745(5) 0.513(4) 0.379(3) 0.028 Uiso 1 1 d . . . H12B H 0.127(5) 0.710(3) -0.027(3) 0.028 Uiso 1 1 d . . . H2A H 0.170(4) 0.489(3) 0.313(2) 0.028 Uiso 1 1 d D . . H2B H 0.105(5) 0.390(3) 0.2290(15) 0.028 Uiso 1 1 d D . . H21A H 0.774(5) 0.671(4) 0.128(3) 0.028 Uiso 1 1 d . . . H13B H 0.289(5) 1.063(4) 0.029(3) 0.028 Uiso 1 1 d . . . H1A H 0.505(4) 0.396(3) 0.261(2) 0.028 Uiso 1 1 d D . . H22A H 0.929(5) 0.604(3) 0.450(2) 0.028 Uiso 1 1 d . . . H11A H 0.298(5) 0.822(4) 0.322(3) 0.028 Uiso 1 1 d . . . H23A H 0.786(5) 0.980(4) 0.490(3) 0.028 Uiso 1 1 d . . . H12C H 0.227(5) 0.605(4) 0.015(2) 0.028 Uiso 1 1 d . . . H4B H 0.926(4) 0.250(3) 0.396(2) 0.028 Uiso 1 1 d D . . H4A H 1.054(4) 0.283(3) 0.343(2) 0.028 Uiso 1 1 d D . . H1B H 0.522(4) 0.337(3) 0.3389(19) 0.028 Uiso 1 1 d D . . H3A H 0.847(4) 0.164(3) 0.2202(19) 0.028 Uiso 1 1 d D . . H3B H 0.676(5) 0.216(4) 0.192(3) 0.080(18) 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 N11 0.0214(14) 0.0308(17) 0.0204(16) 0.0155(14) 0.0045(11) 0.0041(12) N12 0.0130(13) 0.0147(14) 0.0255(16) 0.0051(12) 0.0054(11) 0.0017(11) N13 0.0306(15) 0.0109(14) 0.0197(15) 0.0045(12) 0.0071(12) 0.0007(12) C12 0.0124(14) 0.0189(17) 0.032(2) 0.0133(15) 0.0068(12) 0.0006(12) C13 0.0106(14) 0.0129(15) 0.0213(17) 0.0054(13) 0.0026(11) 0.0003(11) C14 0.0135(14) 0.0160(16) 0.0207(17) 0.0037(13) 0.0050(11) 0.0022(12) C15 0.0213(16) 0.0171(17) 0.0197(17) 0.0034(13) 0.0060(12) 0.0046(13) C16 0.0224(17) 0.0261(19) 0.0217(18) 0.0062(15) 0.0080(13) 0.0071(14) N21 0.0224(14) 0.0226(15) 0.0164(15) 0.0039(12) 0.0035(11) 0.0004(11) N22 0.0145(13) 0.0137(14) 0.0178(14) 0.0053(11) 0.0038(10) 0.0039(10) N23 0.0289(15) 0.0138(14) 0.0235(16) 0.0071(12) 0.0103(12) 0.0045(12) C22 0.0164(15) 0.0204(17) 0.0210(17) 0.0099(14) 0.0021(12) 0.0014(12) C23 0.0114(14) 0.0174(16) 0.0167(16) 0.0085(13) 0.0045(11) 0.0007(11) C24 0.0125(14) 0.0214(17) 0.0212(17) 0.0069(14) 0.0049(12) 0.0046(12) C25 0.0177(15) 0.0171(17) 0.0278(19) 0.0068(14) 0.0048(13) 0.0019(12) C26 0.0142(15) 0.0209(17) 0.0199(17) 0.0079(14) 0.0018(12) -0.0010(12) S1 0.0136(4) 0.0123(4) 0.0156(4) 0.0041(3) 0.0032(3) 0.0016(3) O11 0.0152(10) 0.0202(12) 0.0212(12) 0.0102(9) 0.0076(8) 0.0004(8) O12 0.0208(11) 0.0139(11) 0.0173(11) 0.0074(9) 0.0032(8) 0.0030(8) O13 0.0180(11) 0.0160(12) 0.0313(13) 0.0080(10) 0.0103(9) 0.0074(9) O14 0.0239(11) 0.0161(12) 0.0187(12) 0.0017(9) -0.0044(9) -0.0048(9) S2 0.0144(4) 0.0152(4) 0.0221(4) 0.0070(3) 0.0045(3) 0.0028(3) O21 0.0118(10) 0.0290(13) 0.0193(12) 0.0106(10) 0.0040(8) 0.0002(9) O22 0.0123(10) 0.0333(14) 0.0185(12) 0.0071(10) 0.0018(8) -0.0002(9) O23 0.0206(11) 0.0479(16) 0.0161(12) 0.0113(11) 0.0048(9) -0.0012(10) O24 0.0336(14) 0.0197(14) 0.084(2) 0.0143(14) 0.0138(13) 0.0107(11) O1 0.0202(11) 0.0213(13) 0.0176(12) 0.0074(10) 0.0040(9) 0.0025(9) O2 0.0289(13) 0.0269(14) 0.0217(13) 0.0017(11) 0.0084(10) -0.0016(10) O3 0.0252(12) 0.0319(14) 0.0186(13) 0.0012(11) 0.0012(9) 0.0055(11) O4 0.0226(12) 0.0232(13) 0.0257(13) 0.0066(10) 0.0085(9) 0.0026(10) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 N11 C12 1.340(4) . ? N11 C16 1.349(4) . ? N11 H11A 0.82(4) . ? N12 C13 1.462(4) . ? N12 H12A 0.88(4) . ? N12 H12B 0.93(4) . ? N12 H12C 0.94(4) . ? N13 C14 1.329(4) . ? N13 H13A 0.84(4) . ? N13 H13B 0.87(4) . ? C12 C13 1.363(4) . ? C12 H12 0.9500 . ? C13 C14 1.418(4) . ? C14 C15 1.417(4) . ? C15 C16 1.351(4) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? N21 C26 1.343(4) . ? N21 C22 1.343(4) . ? N21 H21A 0.92(4) . ? N22 C23 1.449(4) . ? N22 H22C 0.84(4) . ? N22 H22B 0.98(4) . ? N22 H22A 0.98(4) . ? N23 C24 1.319(4) . ? N23 H23B 0.87(4) . ? N23 H23A 0.86(4) . ? C22 C23 1.379(4) . ? C22 H22 0.9500 . ? C23 C24 1.412(4) . ? C24 C25 1.428(4) . ? C25 C26 1.347(4) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? S1 O14 1.465(2) . ? S1 O13 1.480(2) . ? S1 O11 1.480(2) . ? S1 O12 1.485(2) . ? S2 O24 1.470(2) . ? S2 O23 1.471(2) . ? S2 O21 1.475(2) . ? S2 O22 1.478(2) . ? O1 H1A 0.834(17) . ? O1 H1B 0.855(17) . ? O2 H2A 0.849(17) . ? O2 H2B 0.850(17) . ? O3 H3A 0.845(18) . ? O3 H3B 0.852(18) . ? O4 H4B 0.867(17) . ? O4 H4A 0.859(17) . ? 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 C12 N11 C16 121.4(3) . . ? C12 N11 H11A 115(3) . . ? C16 N11 H11A 123(3) . . ? C13 N12 H12A 110(2) . . ? C13 N12 H12B 108(2) . . ? H12A N12 H12B 110(3) . . ? C13 N12 H12C 118(2) . . ? H12A N12 H12C 105(3) . . ? H12B N12 H12C 107(3) . . ? C14 N13 H13A 118(3) . . ? C14 N13 H13B 120(2) . . ? H13A N13 H13B 122(4) . . ? N11 C12 C13 119.9(3) . . ? N11 C12 H12 120.1 . . ? C13 C12 H12 120.1 . . ? C12 C13 C14 121.3(3) . . ? C12 C13 N12 120.4(3) . . ? C14 C13 N12 118.2(3) . . ? N13 C14 C15 121.1(3) . . ? N13 C14 C13 123.1(3) . . ? C15 C14 C13 115.8(3) . . ? C16 C15 C14 120.5(3) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? N11 C16 C15 121.1(3) . . ? N11 C16 H16 119.5 . . ? C15 C16 H16 119.5 . . ? C26 N21 C22 120.8(3) . . ? C26 N21 H21A 122(2) . . ? C22 N21 H21A 117(2) . . ? C23 N22 H22C 105(2) . . ? C23 N22 H22B 110(2) . . ? H22C N22 H22B 112(3) . . ? C23 N22 H22A 111(2) . . ? H22C N22 H22A 111(3) . . ? H22B N22 H22A 108(3) . . ? C24 N23 H23B 120(2) . . ? C24 N23 H23A 119(2) . . ? H23B N23 H23A 121(3) . . ? N21 C22 C23 120.3(3) . . ? N21 C22 H22 119.8 . . ? C23 C22 H22 119.8 . . ? C22 C23 C24 120.6(3) . . ? C22 C23 N22 118.1(3) . . ? C24 C23 N22 121.3(3) . . ? N23 C24 C23 123.3(3) . . ? N23 C24 C25 120.7(3) . . ? C23 C24 C25 116.1(3) . . ? C26 C25 C24 120.2(3) . . ? C26 C25 H25 119.9 . . ? C24 C25 H25 119.9 . . ? N21 C26 C25 121.9(3) . . ? N21 C26 H26 119.0 . . ? C25 C26 H26 119.0 . . ? O14 S1 O13 111.27(12) . . ? O14 S1 O11 110.48(13) . . ? O13 S1 O11 108.17(12) . . ? O14 S1 O12 109.04(12) . . ? O13 S1 O12 108.82(12) . . ? O11 S1 O12 109.01(12) . . ? O24 S2 O23 106.83(16) . . ? O24 S2 O21 110.16(14) . . ? O23 S2 O21 110.18(13) . . ? O24 S2 O22 111.72(15) . . ? O23 S2 O22 108.89(12) . . ? O21 S2 O22 109.05(12) . . ? H1A O1 H1B 111(2) . . ? H2A O2 H2B 109(2) . . ? H3A O3 H3B 105(3) . . ? H4B O4 H4A 104(2) . . ? 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 N11 H11A O24 0.82(4) 2.20(4) 2.953(4) 153(3) 2_666 N11 H11A O23 0.82(4) 2.25(4) 2.941(4) 142(3) 2_666 N22 H22C O22 0.84(4) 2.02(4) 2.865(3) 175(3) 2_666 N22 H22C O23 0.84(4) 2.54(3) 2.993(3) 115(3) 2_666 N23 H23B O22 0.87(4) 2.57(4) 3.110(4) 121(3) 2_666 O2 H2A O23 0.849(17) 1.882(18) 2.731(3) 178(4) 2_666 N12 H12A O13 0.88(4) 1.88(4) 2.737(3) 163(3) 2_665 N13 H13A O3 0.84(4) 2.06(4) 2.859(4) 157(3) 2_665 N21 H21A O12 0.92(4) 1.80(4) 2.714(3) 171(3) 2_665 N21 H21A O13 0.92(4) 2.60(4) 3.218(3) 125(3) 2_665 N12 H12B O11 0.93(4) 1.83(4) 2.743(3) 168(3) 2_565 N13 H13B O13 0.87(4) 2.05(4) 2.906(4) 166(3) 1_565 N23 H23A O24 0.86(4) 1.95(4) 2.810(4) 170(3) 1_565 N22 H22A O21 0.98(4) 1.77(4) 2.741(3) 169(3) 2_766 N23 H23B O4 0.87(4) 2.11(4) 2.918(4) 155(3) 2_766 O4 H4A O2 0.859(17) 1.833(19) 2.684(3) 170(3) 1_655 N22 H22B O1 0.98(4) 1.93(4) 2.875(4) 163(3) . N12 H12C O12 0.94(4) 1.84(4) 2.761(3) 167(3) . N12 H12C S1 0.94(4) 2.82(4) 3.734(3) 164(3) . O1 H1A O14 0.834(17) 1.983(18) 2.773(3) 158(3) . O1 H1B O22 0.855(17) 1.967(18) 2.797(3) 163(3) . O1 H1B S2 0.855(17) 2.83(2) 3.475(2) 134(3) . O2 H2B O11 0.850(17) 1.972(17) 2.814(3) 171(3) . O2 H2B S1 0.850(17) 2.84(2) 3.651(2) 160(3) . O3 H3A O4 0.845(18) 2.17(2) 2.976(3) 161(3) . O3 H3B O1 0.852(18) 2.08(3) 2.870(3) 155(4) . O4 H4B O21 0.867(17) 2.04(2) 2.852(3) 155(3) . O4 H4B S2 0.867(17) 2.885(18) 3.724(2) 163(3) . _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.692 _refine_diff_density_min -0.551 _refine_diff_density_rms 0.095 _database_code_depnum_ccdc_archive 'CCDC 959240'