Electronic Supplementary Material for CrystEngComm This Journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Richard Robson' _publ_contact_author_address ; School of Chemistry University of Melbourne Parkville Victoria 3010 AUSTRALIA ; _publ_contact_author_email R.ROBSON@UNIMELB.EDU.AU _publ_section_title ; An Unexpected Network in Guanidinium Rhodizonate ; loop_ _publ_author_name 'Richard Robson' 'Brendan Abrahams' 'Marissa G. Haywood' data_rh30861m _database_code_depnum_ccdc_archive 'CCDC 284214' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'guanidinium rhodizonate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H12 N6 O6' _chemical_formula_weight 288.24 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 3.641(5) _cell_length_b 9.363(14) _cell_length_c 17.51(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.50(2) _cell_angle_gamma 90.00 _cell_volume 596.5(15) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 140 _cell_measurement_theta_min 2.47 _cell_measurement_theta_max 12.47 _exptl_crystal_description rod _exptl_crystal_colour black _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.605 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 300 _exptl_absorpt_coefficient_mu 0.138 _exptl_absorpt_correction_type None _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2381 _diffrn_reflns_av_R_equivalents 0.2651 _diffrn_reflns_av_sigmaI/netI 0.3067 _diffrn_reflns_limit_h_min -3 _diffrn_reflns_limit_h_max 3 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 22.50 _reflns_number_total 772 _reflns_number_gt 238 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Owing to difficulties associated with finding a crystal which was suitable for a single crystal X-ray study, the crystal used was small and weakly diffracting. Although the weak data led to elevated agreement values the atoms in the structure are clearly defined. Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0952P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 772 _refine_ls_number_parameters 91 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2317 _refine_ls_R_factor_gt 0.0986 _refine_ls_wR_factor_ref 0.2572 _refine_ls_wR_factor_gt 0.2223 _refine_ls_goodness_of_fit_ref 0.826 _refine_ls_restrained_S_all 0.826 _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 0.236(2) 0.6285(10) 0.3703(5) 0.086(3) Uani 1 1 d . . . N3 N 0.675(2) 1.0914(10) 0.2934(5) 0.059(3) Uani 1 1 d . . . H3A H 0.6382 1.1686 0.3186 0.070 Uiso 1 1 calc R . . H3B H 0.6245 1.0886 0.2450 0.070 Uiso 1 1 calc R . . O2 O 0.245(2) 0.7723(9) 0.5068(4) 0.083(3) Uani 1 1 d . . . N2 N 0.883(2) 0.8648(9) 0.2862(5) 0.064(3) Uani 1 1 d . . . H2A H 0.9863 0.7906 0.3066 0.077 Uiso 1 1 calc R . . H2B H 0.8291 0.8665 0.2379 0.077 Uiso 1 1 calc R . . O3 O 0.537(3) 0.6451(10) 0.6357(5) 0.096(3) Uani 1 1 d . . . N1 N 0.887(2) 0.9771(10) 0.4021(5) 0.066(3) Uani 1 1 d . . . H1A H 0.8528 1.0531 0.4285 0.079 Uiso 1 1 calc R . . H1B H 0.9734 0.9014 0.4241 0.079 Uiso 1 1 calc R . . C2 C 0.355(3) 0.6464(14) 0.5022(7) 0.055(3) Uani 1 1 d . . . C3 C 0.520(3) 0.5835(13) 0.5734(8) 0.062(4) Uani 1 1 d . . . C1 C 0.351(3) 0.5721(13) 0.4311(7) 0.050(3) Uani 1 1 d . . . C4 C 0.808(3) 0.9768(14) 0.3293(7) 0.057(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.102(8) 0.095(7) 0.061(6) 0.016(6) -0.005(5) 0.034(6) N3 0.075(7) 0.037(6) 0.064(6) 0.000(6) 0.001(5) 0.005(6) O2 0.124(8) 0.031(5) 0.096(7) 0.009(5) 0.017(6) 0.032(5) N2 0.078(8) 0.036(6) 0.079(7) -0.005(6) 0.005(6) 0.015(6) O3 0.132(9) 0.094(7) 0.063(6) -0.030(6) 0.000(6) 0.025(7) N1 0.094(9) 0.059(7) 0.044(6) 0.001(6) 0.002(6) 0.008(6) C2 0.059(9) 0.057(10) 0.050(7) 0.003(8) 0.014(6) 0.001(8) C3 0.059(9) 0.053(9) 0.073(10) 0.001(8) 0.006(7) 0.017(7) C1 0.048(8) 0.058(9) 0.045(8) -0.005(7) 0.010(6) -0.005(7) C4 0.064(10) 0.055(9) 0.051(8) 0.016(8) -0.002(7) 0.010(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.246(11) . ? N3 C4 1.325(13) . ? O2 C2 1.248(13) . ? N2 C4 1.326(13) . ? O3 C3 1.232(12) . ? N1 C4 1.296(12) . ? C2 C1 1.426(14) . ? C2 C3 1.482(15) . ? C3 C1 1.534(16) 3_666 ? C1 C3 1.534(16) 3_666 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 C2 C1 121.8(12) . . ? O2 C2 C3 116.1(11) . . ? C1 C2 C3 121.9(12) . . ? O3 C3 C2 124.2(12) . . ? O3 C3 C1 119.1(12) . 3_666 ? C2 C3 C1 116.6(11) . 3_666 ? O1 C1 C2 122.0(12) . . ? O1 C1 C3 116.8(11) . 3_666 ? C2 C1 C3 121.1(11) . 3_666 ? N1 C4 N3 121.7(13) . . ? N1 C4 N2 121.3(12) . . ? N3 C4 N2 116.8(10) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 22.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.274 _refine_diff_density_min -0.277 _refine_diff_density_rms 0.082