# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_gi120d _database_code_depnum_ccdc_archive 'CCDC 914573' #TrackingRef 'web_deposit_cif_file_0_MarekSzafranski_1358248656.gi120d.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'guanidinium iodide' _chemical_melting_point 460(5) _chemical_formula_moiety ? _chemical_formula_sum 'C H6 I N3' _chemical_formula_weight 186.99 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting hexagonal _symmetry_space_group_name_H-M P6(3)mc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-x, -y, z+1/2' 'y, -x+y, z+1/2' 'x-y, x, z+1/2' '-y, -x, z' '-x+y, y, z' 'x, x-y, z' 'y, x, z+1/2' 'x-y, -y, z+1/2' '-x, -x+y, z+1/2' _cell_length_a 7.15120(5) _cell_length_b 7.15120(5) _cell_length_c 11.96300(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 529.820(7) _cell_formula_units_Z 4 _cell_measurement_temperature 120.0(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.344 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 5.892 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.76284 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'CrysalisPro (Oxford Diffraction 2010)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120.0(1) _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 'Gemini A Ultra' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15935 _diffrn_reflns_av_R_equivalents 0.0247 _diffrn_reflns_av_sigmaI/netI 0.0080 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.29 _diffrn_reflns_theta_max 32.24 _reflns_number_total 757 _reflns_number_gt 742 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. 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^)+(0.0111P)^2^+0.1782P] 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 SHELXL _refine_ls_extinction_coef 0.0015(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(4) _refine_ls_number_reflns 757 _refine_ls_number_parameters 29 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0118 _refine_ls_R_factor_gt 0.0111 _refine_ls_wR_factor_ref 0.0283 _refine_ls_wR_factor_gt 0.0282 _refine_ls_goodness_of_fit_ref 1.418 _refine_ls_restrained_S_all 1.417 _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 I1 I 0.6667 0.3333 0.1617 0.01414(6) Uani 1 6 d S . . I2A I 0.0000 0.0000 0.3382(5) 0.0256(8) Uani 0.50 6 d SP . . I2B I 0.0000 0.0000 0.3176(5) 0.0204(5) Uani 0.50 6 d SP . . C1 C 0.3333 0.6667 -0.9156(3) 0.0141(7) Uani 1 6 d S . . N2 N 0.1197(3) 0.55986(16) -0.64067(16) 0.0164(3) Uani 1 2 d S . . H2A H 0.0503 0.6293 -0.6403 0.020 Uiso 0.50 1 calc PR . . H2B H 0.0503 0.4210 -0.6409 0.020 Uiso 0.50 1 calc PR . . N1 N 0.22641(16) 0.77359(16) -0.91632(19) 0.0200(4) Uani 1 2 d S . . H1A H 0.0876 0.7042 -0.9172 0.024 Uiso 0.50 1 calc PR . . H1B H 0.2958 0.9124 -0.9159 0.024 Uiso 0.50 1 calc PR . . C2 C 0.3333 0.6667 -0.6410(3) 0.0132(7) Uani 1 6 d S . . 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 I1 0.01292(7) 0.01292(7) 0.01660(9) 0.000 0.000 0.00646(3) I2A 0.0123(4) 0.0123(4) 0.052(2) 0.000 0.000 0.0062(2) I2B 0.0113(4) 0.0113(4) 0.0387(13) 0.000 0.000 0.0056(2) C1 0.0151(10) 0.0151(10) 0.0122(15) 0.000 0.000 0.0075(5) N2 0.0123(8) 0.0138(6) 0.0225(9) -0.0008(3) -0.0016(7) 0.0062(4) N1 0.0159(6) 0.0159(6) 0.0303(10) 0.0010(4) -0.0010(4) 0.0095(7) C2 0.0142(10) 0.0142(10) 0.0113(14) 0.000 0.000 0.0071(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.324(2) . ? C1 N1 1.324(2) 2_665 ? C1 N1 1.324(2) 3_565 ? N2 C2 1.323(2) . ? C2 N2 1.323(2) 3_565 ? C2 N2 1.323(2) 2_665 ? 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 C1 N1 119.996(5) . 2_665 ? N1 C1 N1 119.996(5) . 3_565 ? N1 C1 N1 119.996(5) 2_665 3_565 ? N2 C2 N2 119.999(2) . 3_565 ? N2 C2 N2 119.999(3) . 2_665 ? N2 C2 N2 119.999(2) 3_565 2_665 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 32.24 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.309 _refine_diff_density_min -0.543 _refine_diff_density_rms 0.060 data_ttgi_150d _database_code_depnum_ccdc_archive 'CCDC 914574' #TrackingRef 'web_deposit_cif_file_1_MarekSzafranski_1358248656.ttgi_150d.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'guanidinium iodide' _chemical_melting_point 460(5) _chemical_formula_moiety ? _chemical_formula_sum 'C H6 I N3' _chemical_formula_weight 186.99 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting hexagonal _symmetry_space_group_name_H-M P6(3)mc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-x, -y, z+1/2' 'y, -x+y, z+1/2' 'x-y, x, z+1/2' '-y, -x, z' '-x+y, y, z' 'x, x-y, z' 'y, x, z+1/2' 'x-y, -y, z+1/2' '-x, -x+y, z+1/2' _cell_length_a 7.16410(17) _cell_length_b 7.16410(17) _cell_length_c 12.0317(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 534.79(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150.0(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.322 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 5.837 _exptl_absorpt_correction_T_min 0.76361 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'CrysalisPro (Oxford Diffraction 2010)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150.0(1) _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 'Gemini A Ultra' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7466 _diffrn_reflns_av_R_equivalents 0.0255 _diffrn_reflns_av_sigmaI/netI 0.0115 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.28 _diffrn_reflns_theta_max 32.35 _reflns_number_total 752 _reflns_number_gt 719 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. 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^)+(0.0271P)^2^+0.5434P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.04(7) _refine_ls_number_reflns 752 _refine_ls_number_parameters 28 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0212 _refine_ls_R_factor_gt 0.0198 _refine_ls_wR_factor_ref 0.0523 _refine_ls_wR_factor_gt 0.0516 _refine_ls_goodness_of_fit_ref 1.205 _refine_ls_restrained_S_all 1.204 _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 I1 I 0.6667 0.3333 0.1614 0.01984(10) Uani 1 6 d S . . I2A I 0.0000 0.0000 0.3421(6) 0.0346(12) Uani 0.50 6 d SP . . I2B I 0.0000 0.0000 0.3183(6) 0.0286(8) Uani 0.50 6 d SP . . C1 C 0.3333 0.6667 -0.9151(6) 0.0201(12) Uani 1 6 d S . . N2 N 0.1208(6) 0.5604(3) -0.6408(3) 0.0226(6) Uani 1 2 d S . . H2A H 0.0515 0.6297 -0.6401 0.027 Uiso 0.50 1 calc PR . . H2B H 0.0515 0.4218 -0.6412 0.027 Uiso 0.50 1 calc PR . . N1 N 0.2268(3) 0.7732(3) -0.9154(3) 0.0276(7) Uani 1 2 d S . . H1A H 0.2961 0.9118 -0.9159 0.033 Uiso 0.50 1 calc PR . . H1B H 0.0882 0.7039 -0.9152 0.033 Uiso 0.50 1 calc PR . . C2 C 0.3333 0.6667 -0.6413(6) 0.0175(12) Uani 1 6 d S . . 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 I1 0.01718(11) 0.01718(11) 0.02516(15) 0.000 0.000 0.00859(6) I2A 0.0159(7) 0.0159(7) 0.072(4) 0.000 0.000 0.0079(4) I2B 0.0147(7) 0.0147(7) 0.056(2) 0.000 0.000 0.0074(3) C1 0.0209(19) 0.0209(19) 0.018(3) 0.000 0.000 0.0104(9) N2 0.0151(14) 0.0176(11) 0.0342(17) -0.0010(6) -0.0020(13) 0.0076(7) N1 0.0205(11) 0.0205(11) 0.0440(19) 0.0024(8) -0.0024(8) 0.0120(13) C2 0.0171(18) 0.0171(18) 0.018(3) 0.000 0.000 0.0085(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.322(4) . ? C1 N1 1.322(4) 3_565 ? C1 N1 1.322(4) 2_665 ? N2 C2 1.319(4) . ? C2 N2 1.319(4) 3_565 ? C2 N2 1.319(4) 2_665 ? 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 C1 N1 119.999(6) . 3_565 ? N1 C1 N1 119.999(7) . 2_665 ? N1 C1 N1 119.999(6) 3_565 2_665 ? N2 C2 N2 119.997(7) 3_565 . ? N2 C2 N2 119.997(7) 3_565 2_665 ? N2 C2 N2 119.997(8) . 2_665 ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 32.35 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.883 _refine_diff_density_min -0.480 _refine_diff_density_rms 0.073 data_ttgi_200d _database_code_depnum_ccdc_archive 'CCDC 914575' #TrackingRef 'web_deposit_cif_file_2_MarekSzafranski_1358248656.ttgi_200d.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'guanidinium iodide' _chemical_melting_point 460(5) _chemical_formula_moiety ? _chemical_formula_sum 'C H6 I N3' _chemical_formula_weight 186.99 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting hexagonal _symmetry_space_group_name_H-M P6(3)mc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-x, -y, z+1/2' 'y, -x+y, z+1/2' 'x-y, x, z+1/2' '-y, -x, z' '-x+y, y, z' 'x, x-y, z' 'y, x, z+1/2' 'x-y, -y, z+1/2' '-x, -x+y, z+1/2' _cell_length_a 7.17619(14) _cell_length_b 7.17619(14) _cell_length_c 12.1229(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 540.66(2) _cell_formula_units_Z 4 _cell_measurement_temperature 200.0(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.297 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 5.774 _exptl_absorpt_correction_T_min 0.73697 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'CrysalisPro (Oxford Diffraction 2010)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 200.0(1) _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 'Gemini A Ultra' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7556 _diffrn_reflns_av_R_equivalents 0.0247 _diffrn_reflns_av_sigmaI/netI 0.0113 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.28 _diffrn_reflns_theta_max 32.20 _reflns_number_total 757 _reflns_number_gt 721 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. 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^)+(0.0213P)^2^+0.1979P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.02(6) _refine_ls_number_reflns 757 _refine_ls_number_parameters 28 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0186 _refine_ls_R_factor_gt 0.0167 _refine_ls_wR_factor_ref 0.0447 _refine_ls_wR_factor_gt 0.0441 _refine_ls_goodness_of_fit_ref 1.259 _refine_ls_restrained_S_all 1.258 _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 I1 I 0.6667 0.3333 0.16016(2) 0.02638(8) Uani 1 6 d S . . I2A I 0.0000 0.0000 0.3491(3) 0.0431(7) Uani 0.50 6 d SP . . I2B I 0.0000 0.0000 0.3180(3) 0.0363(6) Uani 0.50 6 d SP . . C1 C 0.3333 0.6667 -0.9152(5) 0.0258(11) Uani 1 6 d S . . N2 N 0.1212(5) 0.5606(2) -0.6417(3) 0.0298(6) Uani 1 2 d S . . H2A H 0.0520 0.6298 -0.6407 0.036 Uiso 0.50 1 calc PR . . H2B H 0.0520 0.4222 -0.6422 0.036 Uiso 0.50 1 calc PR . . N1 N 0.2269(2) 0.7731(2) -0.9163(3) 0.0359(6) Uani 1 2 d S . . H1A H 0.2960 0.9115 -0.9179 0.043 Uiso 0.50 1 calc PR . . H1B H 0.0885 0.7040 -0.9156 0.043 Uiso 0.50 1 calc PR . . C2 C 0.3333 0.6667 -0.6424(5) 0.0236(10) Uani 1 6 d S . . 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 I1 0.02308(10) 0.02308(10) 0.03298(14) 0.000 0.000 0.01154(5) I2A 0.0224(5) 0.0224(5) 0.0844(19) 0.000 0.000 0.0112(3) I2B 0.0191(5) 0.0191(5) 0.0707(15) 0.000 0.000 0.0095(2) C1 0.0261(17) 0.0261(17) 0.025(2) 0.000 0.000 0.0130(8) N2 0.0196(12) 0.0236(10) 0.0448(16) -0.0012(6) -0.0024(13) 0.0098(6) N1 0.0274(10) 0.0274(10) 0.0562(18) 0.0029(7) -0.0029(7) 0.0163(12) C2 0.0234(16) 0.0234(16) 0.024(2) 0.000 0.000 0.0117(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 C1 N1 1.324(3) . ? C1 N1 1.324(3) 3_565 ? C1 N1 1.324(3) 2_665 ? N2 C2 1.318(3) . ? C2 N2 1.318(3) 3_565 ? C2 N2 1.318(3) 2_665 ? 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 C1 N1 119.988(13) . 3_565 ? N1 C1 N1 119.988(14) . 2_665 ? N1 C1 N1 119.988(13) 3_565 2_665 ? N2 C2 N2 119.995(8) . 3_565 ? N2 C2 N2 119.995(9) . 2_665 ? N2 C2 N2 119.995(8) 3_565 2_665 ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 32.20 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.320 _refine_diff_density_min -0.468 _refine_diff_density_rms 0.058 data_ttgi_250d _database_code_depnum_ccdc_archive 'CCDC 914576' #TrackingRef 'web_deposit_cif_file_3_MarekSzafranski_1358248656.ttgi_250d.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'guanidinium iodide' _chemical_melting_point 460(5) _chemical_formula_moiety ? _chemical_formula_sum 'C H6 I N3' _chemical_formula_weight 186.99 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting hexagonal _symmetry_space_group_name_H-M P6(3)mc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-x, -y, z+1/2' 'y, -x+y, z+1/2' 'x-y, x, z+1/2' '-y, -x, z' '-x+y, y, z' 'x, x-y, z' 'y, x, z+1/2' 'x-y, -y, z+1/2' '-x, -x+y, z+1/2' _cell_length_a 7.18791(13) _cell_length_b 7.18791(13) _cell_length_c 12.2290(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 547.18(2) _cell_formula_units_Z 4 _cell_measurement_temperature 250.0(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.270 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 5.705 _exptl_absorpt_correction_T_min 0.76584 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'CrysalisPro (Oxford Diffraction 2010)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 250.0(1) _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 'Gemini A Ultra' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7714 _diffrn_reflns_av_R_equivalents 0.0230 _diffrn_reflns_av_sigmaI/netI 0.0104 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.27 _diffrn_reflns_theta_max 32.13 _reflns_number_total 763 _reflns_number_gt 714 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. 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^)+(0.0193P)^2^+0.0628P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.03(5) _refine_ls_number_reflns 763 _refine_ls_number_parameters 28 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0185 _refine_ls_R_factor_gt 0.0155 _refine_ls_wR_factor_ref 0.0404 _refine_ls_wR_factor_gt 0.0395 _refine_ls_goodness_of_fit_ref 1.257 _refine_ls_restrained_S_all 1.256 _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 I1 I 0.3333 0.6667 0.840141(7) 0.03381(8) Uani 1 6 d S . . I2A I 1.0000 1.0000 0.6436(2) 0.0530(6) Uani 0.50 6 d SP . . I2B I 1.0000 1.0000 0.6799(2) 0.0472(6) Uani 0.50 6 d SP . . C1 C 0.6667 0.3333 1.9146(4) 0.0338(11) Uani 1 6 d S . . N2 N 0.8785(4) 0.4392(2) 1.6422(3) 0.0378(5) Uani 1 2 d S . . H2A H 0.9475 0.3702 1.6415 0.045 Uiso 0.50 1 calc PR . . H2B H 0.9476 0.5774 1.6426 0.045 Uiso 0.50 1 calc PR . . N1 N 0.7729(2) 0.2271(2) 1.9154(2) 0.0456(7) Uani 1 2 d S . . H1A H 0.9110 0.2962 1.9164 0.055 Uiso 0.50 1 calc PR . . H1B H 0.7038 0.0890 1.9149 0.055 Uiso 0.50 1 calc PR . . C2 C 0.6667 0.3333 1.6428(4) 0.0299(9) Uani 1 6 d S . . 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 I1 0.02992(9) 0.02992(9) 0.04159(13) 0.000 0.000 0.01496(5) I2A 0.0288(4) 0.0288(4) 0.1016(17) 0.000 0.000 0.0144(2) I2B 0.0251(4) 0.0251(4) 0.0913(16) 0.000 0.000 0.0125(2) C1 0.0337(16) 0.0337(16) 0.034(2) 0.000 0.000 0.0169(8) N2 0.0252(11) 0.0308(9) 0.0555(14) -0.0014(6) -0.0029(13) 0.0126(5) N1 0.0372(10) 0.0372(10) 0.0686(18) 0.0030(7) -0.0030(7) 0.0232(12) C2 0.0300(14) 0.0300(14) 0.030(2) 0.000 0.000 0.0150(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.323(3) . ? C1 N1 1.323(3) 2_655 ? C1 N1 1.323(3) 3_665 ? N2 C2 1.318(3) . ? C2 N2 1.318(3) 3_665 ? C2 N2 1.318(3) 2_655 ? 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 C1 N1 119.995(11) . 2_655 ? N1 C1 N1 119.995(11) . 3_665 ? N1 C1 N1 119.995(8) 2_655 3_665 ? N2 C2 N2 119.997(6) . 3_665 ? N2 C2 N2 119.997(8) . 2_655 ? N2 C2 N2 119.997(8) 3_665 2_655 ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 32.13 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.218 _refine_diff_density_min -0.393 _refine_diff_density_rms 0.056 data_ttgi_280d _database_code_depnum_ccdc_archive 'CCDC 914577' #TrackingRef 'web_deposit_cif_file_4_MarekSzafranski_1358248656.ttgi_280d.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'guanidinium iodide' _chemical_melting_point 460(5) _chemical_formula_moiety ? _chemical_formula_sum 'C H6 I N3' _chemical_formula_weight 186.99 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting hexagonal _symmetry_space_group_name_H-M P6(3)mc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-x, -y, z+1/2' 'y, -x+y, z+1/2' 'x-y, x, z+1/2' '-y, -x, z' '-x+y, y, z' 'x, x-y, z' 'y, x, z+1/2' 'x-y, -y, z+1/2' '-x, -x+y, z+1/2' _cell_length_a 7.19508(11) _cell_length_b 7.19508(11) _cell_length_c 12.2986(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 551.388(16) _cell_formula_units_Z 4 _cell_measurement_temperature 280.0(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.253 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 5.661 _exptl_absorpt_correction_T_min 0.72653 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'CrysalisPro (Oxford Diffraction 2010)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 280.0(1) _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 'Gemini A ultra' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7826 _diffrn_reflns_av_R_equivalents 0.0238 _diffrn_reflns_av_sigmaI/netI 0.0109 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.27 _diffrn_reflns_theta_max 32.18 _reflns_number_total 771 _reflns_number_gt 719 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. 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^)+(0.0212P)^2^+0.0743P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.01(6) _refine_ls_number_reflns 771 _refine_ls_number_parameters 28 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0192 _refine_ls_R_factor_gt 0.0161 _refine_ls_wR_factor_ref 0.0430 _refine_ls_wR_factor_gt 0.0421 _refine_ls_goodness_of_fit_ref 1.195 _refine_ls_restrained_S_all 1.194 _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 I1 I 0.6667 0.3333 0.15986(3) 0.03911(9) Uani 1 6 d S . . I2A I 0.0000 0.0000 0.3605(3) 0.0593(7) Uani 0.50 6 d SP . . I2B I 0.0000 0.0000 0.3216(2) 0.0552(7) Uani 0.50 6 d SP . . C1 C 0.3333 0.6667 -0.9137(5) 0.0389(12) Uani 1 6 d S . . N2 N 0.1217(4) 0.5609(2) -0.6422(3) 0.0435(6) Uani 1 2 d S . . H2A H 0.0527 0.6299 -0.6410 0.052 Uiso 0.50 1 calc PR . . H2B H 0.0527 0.4228 -0.6427 0.052 Uiso 0.50 1 calc PR . . N1 N 0.2275(2) 0.7725(2) -0.9144(3) 0.0529(8) Uani 1 2 d S . . H1A H 0.2965 0.9105 -0.9153 0.063 Uiso 0.50 1 calc PR . . H1B H 0.0895 0.7035 -0.9140 0.063 Uiso 0.50 1 calc PR . . C2 C 0.3333 0.6667 -0.6430(4) 0.0347(10) Uani 1 6 d S . . 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 I1 0.03474(10) 0.03474(10) 0.04786(15) 0.000 0.000 0.01737(5) I2A 0.0331(4) 0.0331(4) 0.1118(19) 0.000 0.000 0.0166(2) I2B 0.0292(4) 0.0292(4) 0.107(2) 0.000 0.000 0.0146(2) C1 0.0397(18) 0.0397(18) 0.037(2) 0.000 0.000 0.0199(9) N2 0.0303(12) 0.0355(9) 0.0629(15) -0.0022(7) -0.0043(14) 0.0152(6) N1 0.0420(11) 0.0420(11) 0.080(2) 0.0039(7) -0.0039(7) 0.0252(13) C2 0.0353(15) 0.0353(15) 0.034(2) 0.000 0.000 0.0176(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 C1 N1 1.319(3) . ? C1 N1 1.319(3) 3_565 ? C1 N1 1.319(3) 2_665 ? N2 C2 1.319(3) . ? C2 N2 1.319(3) 3_565 ? C2 N2 1.319(3) 2_665 ? 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 C1 N1 119.996(8) . 3_565 ? N1 C1 N1 119.996(8) . 2_665 ? N1 C1 N1 119.996(8) 3_565 2_665 ? N2 C2 N2 119.994(9) 3_565 . ? N2 C2 N2 119.994(9) 3_565 2_665 ? N2 C2 N2 119.994(10) . 2_665 ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 32.18 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.201 _refine_diff_density_min -0.383 _refine_diff_density_rms 0.060 data_ttgi_300d _database_code_depnum_ccdc_archive 'CCDC 914578' #TrackingRef 'web_deposit_cif_file_5_MarekSzafranski_1358248656.ttgi_300d.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'guanidinium iodide' _chemical_melting_point 460(5) _chemical_formula_moiety ? _chemical_formula_sum 'C H6 I N3' _chemical_formula_weight 186.99 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting hexagonal _symmetry_space_group_name_H-M P6(3)mc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-x, -y, z+1/2' 'y, -x+y, z+1/2' 'x-y, x, z+1/2' '-y, -x, z' '-x+y, y, z' 'x, x-y, z' 'y, x, z+1/2' 'x-y, -y, z+1/2' '-x, -x+y, z+1/2' _cell_length_a 7.20163(11) _cell_length_b 7.20163(11) _cell_length_c 12.3501(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 554.704(18) _cell_formula_units_Z 4 _cell_measurement_temperature 300.0(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.239 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 5.628 _exptl_absorpt_correction_T_min 0.74807 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'CrysalisPro (Oxford Diffraction 2010)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 300.0(1) _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 'Gemini A Ultra' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7867 _diffrn_reflns_av_R_equivalents 0.0230 _diffrn_reflns_av_sigmaI/netI 0.0106 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.27 _diffrn_reflns_theta_max 32.04 _reflns_number_total 776 _reflns_number_gt 713 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. 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^)+(0.0188P)^2^+0.0982P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.06(6) _refine_ls_number_reflns 776 _refine_ls_number_parameters 28 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0203 _refine_ls_R_factor_gt 0.0169 _refine_ls_wR_factor_ref 0.0416 _refine_ls_wR_factor_gt 0.0407 _refine_ls_goodness_of_fit_ref 1.186 _refine_ls_restrained_S_all 1.185 _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 I1 I 0.6667 0.3333 0.15969(4) 0.04316(9) Uani 1 6 d S . . I2A I 0.0000 0.0000 0.3630(3) 0.0642(8) Uani 0.50 6 d SP . . I2B I 0.0000 0.0000 0.3226(2) 0.0614(8) Uani 0.50 6 d SP . . C1 C 0.3333 0.6667 -0.9133(5) 0.0423(12) Uani 1 6 d S . . N2 N 0.1219(4) 0.5609(2) -0.6421(3) 0.0477(6) Uani 1 2 d S . . H2A H 0.0529 0.6299 -0.6412 0.057 Uiso 0.50 1 calc PR . . H2B H 0.0529 0.4230 -0.6426 0.057 Uiso 0.50 1 calc PR . . N1 N 0.2274(2) 0.7726(2) -0.9142(3) 0.0589(8) Uani 1 2 d S . . H1A H 0.2963 0.9105 -0.9153 0.071 Uiso 0.50 1 calc PR . . H1B H 0.0895 0.7037 -0.9136 0.071 Uiso 0.50 1 calc PR . . C2 C 0.3333 0.6667 -0.6429(4) 0.0372(10) Uani 1 6 d S . . 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 I1 0.03823(10) 0.03823(10) 0.05301(15) 0.000 0.000 0.01911(5) I2A 0.0362(4) 0.0362(4) 0.120(2) 0.000 0.000 0.0181(2) I2B 0.0325(4) 0.0325(4) 0.119(2) 0.000 0.000 0.0162(2) C1 0.0431(18) 0.0431(18) 0.041(2) 0.000 0.000 0.0216(9) N2 0.0326(12) 0.0387(10) 0.0697(16) -0.0019(7) -0.0038(15) 0.0163(6) N1 0.0459(12) 0.0459(12) 0.091(2) 0.0038(8) -0.0038(8) 0.0272(14) C2 0.0379(15) 0.0379(15) 0.036(2) 0.000 0.000 0.0189(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 C1 N1 1.321(3) . ? C1 N1 1.321(3) 3_565 ? C1 N1 1.321(3) 2_665 ? N2 C2 1.319(3) . ? C2 N2 1.319(3) 3_565 ? C2 N2 1.319(3) 2_665 ? 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 C1 N1 119.993(10) . 3_565 ? N1 C1 N1 119.993(10) . 2_665 ? N1 C1 N1 119.993(10) 3_565 2_665 ? N2 C2 N2 119.996(8) . 3_565 ? N2 C2 N2 119.996(8) . 2_665 ? N2 C2 N2 119.996(8) 3_565 2_665 ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 32.04 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.228 _refine_diff_density_min -0.350 _refine_diff_density_rms 0.060 data_ttgi_320d _database_code_depnum_ccdc_archive 'CCDC 914579' #TrackingRef 'web_deposit_cif_file_6_MarekSzafranski_1358248656.ttgi_320d.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'guanidinium iodide' _chemical_melting_point 460(5) _chemical_formula_moiety ? _chemical_formula_sum 'C H6 I N3' _chemical_formula_weight 186.99 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting hexagonal _symmetry_space_group_name_H-M P6(3)mc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-x, -y, z+1/2' 'y, -x+y, z+1/2' 'x-y, x, z+1/2' '-y, -x, z' '-x+y, y, z' 'x, x-y, z' 'y, x, z+1/2' 'x-y, -y, z+1/2' '-x, -x+y, z+1/2' _cell_length_a 7.20634(14) _cell_length_b 7.20634(14) _cell_length_c 12.4020(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 557.77(2) _cell_formula_units_Z 4 _cell_measurement_temperature 320.0(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.227 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 5.597 _exptl_absorpt_correction_T_min 0.72653 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'CrysalisPro (Oxford Diffraction 2010)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 320.0(1) _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 'Gemini A Ultra' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7920 _diffrn_reflns_av_R_equivalents 0.0222 _diffrn_reflns_av_sigmaI/netI 0.0103 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.26 _diffrn_reflns_theta_max 31.91 _reflns_number_total 778 _reflns_number_gt 715 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. 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^)+(0.0191P)^2^+0.0915P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.01(6) _refine_ls_number_reflns 778 _refine_ls_number_parameters 28 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0228 _refine_ls_R_factor_gt 0.0187 _refine_ls_wR_factor_ref 0.0443 _refine_ls_wR_factor_gt 0.0431 _refine_ls_goodness_of_fit_ref 1.219 _refine_ls_restrained_S_all 1.218 _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 I1 I 0.3333 0.6667 0.84075(5) 0.04746(10) Uani 1 6 d S . . I2A I 1.0000 1.0000 0.6344(3) 0.0691(9) Uani 0.50 6 d SP . . I2B I 1.0000 1.0000 0.6766(2) 0.0670(9) Uani 0.50 6 d SP . . C1 C 0.6667 0.3333 1.9130(5) 0.0465(13) Uani 1 6 d S . . N2 N 0.8777(5) 0.4389(2) 1.6425(3) 0.0521(6) Uani 1 2 d S . . H2A H 0.9466 0.3700 1.6414 0.062 Uiso 0.50 1 calc PR . . H2B H 0.9466 0.5767 1.6430 0.062 Uiso 0.50 1 calc PR . . N1 N 0.7725(3) 0.2275(3) 1.9138(3) 0.0640(9) Uani 1 2 d S . . H1A H 0.7036 0.0897 1.9149 0.077 Uiso 0.50 1 calc PR . . H1B H 0.9103 0.2964 1.9133 0.077 Uiso 0.50 1 calc PR . . C2 C 0.6667 0.3333 1.6433(4) 0.0402(11) Uani 1 6 d S . . 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 I1 0.04197(12) 0.04197(12) 0.05844(17) 0.000 0.000 0.02098(6) I2A 0.0403(5) 0.0403(5) 0.127(3) 0.000 0.000 0.0202(2) I2B 0.0349(4) 0.0349(4) 0.131(3) 0.000 0.000 0.0175(2) C1 0.047(2) 0.047(2) 0.046(3) 0.000 0.000 0.0233(10) N2 0.0371(14) 0.0422(11) 0.0752(18) -0.0023(8) -0.0046(16) 0.0185(7) N1 0.0490(13) 0.0490(13) 0.100(3) 0.0053(9) -0.0053(9) 0.0287(15) C2 0.0411(17) 0.0411(17) 0.038(2) 0.000 0.000 0.0206(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 I2A I2B 0.524(6) . ? C1 N1 1.321(3) . ? C1 N1 1.321(3) 3_665 ? C1 N1 1.321(3) 2_655 ? N2 C2 1.317(3) . ? C2 N2 1.317(3) 3_665 ? C2 N2 1.317(3) 2_655 ? 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 C1 N1 119.994(13) . 3_665 ? N1 C1 N1 119.994(14) . 2_655 ? N1 C1 N1 119.994(10) 3_665 2_655 ? N2 C2 N2 119.994(10) 3_665 . ? N2 C2 N2 119.994(12) 3_665 2_655 ? N2 C2 N2 119.994(12) . 2_655 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 31.91 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.200 _refine_diff_density_min -0.411 _refine_diff_density_rms 0.058 data_ttgi_340d _database_code_depnum_ccdc_archive 'CCDC 914580' #TrackingRef 'web_deposit_cif_file_7_MarekSzafranski_1358248656.ttgi_340d.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'guanidinium iodide' _chemical_melting_point 460(5) _chemical_formula_moiety ? _chemical_formula_sum 'C H6 I N3' _chemical_formula_weight 186.99 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting hexagonal _symmetry_space_group_name_H-M P6(3)mc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-x, -y, z+1/2' 'y, -x+y, z+1/2' 'x-y, x, z+1/2' '-y, -x, z' '-x+y, y, z' 'x, x-y, z' 'y, x, z+1/2' 'x-y, -y, z+1/2' '-x, -x+y, z+1/2' _cell_length_a 7.21109(19) _cell_length_b 7.21109(19) _cell_length_c 12.4610(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 561.16(3) _cell_formula_units_Z 4 _cell_measurement_temperature 340.0(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.213 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 5.563 _exptl_absorpt_correction_T_min 0.78053 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'CrysalisPro (Oxford Diffraction 2010)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 340.0(1) _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 'Gemini A Ultra' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7972 _diffrn_reflns_av_R_equivalents 0.0232 _diffrn_reflns_av_sigmaI/netI 0.0106 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.26 _diffrn_reflns_theta_max 32.31 _reflns_number_total 789 _reflns_number_gt 706 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. 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^)+(0.0234P)^2^+0.0530P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.04(7) _refine_ls_number_reflns 789 _refine_ls_number_parameters 28 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0254 _refine_ls_R_factor_gt 0.0206 _refine_ls_wR_factor_ref 0.0493 _refine_ls_wR_factor_gt 0.0479 _refine_ls_goodness_of_fit_ref 1.183 _refine_ls_restrained_S_all 1.183 _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 I1 I 0.6667 0.3333 0.15872(6) 0.05232(11) Uani 1 6 d S . . I2A I 0.0000 0.0000 0.3680(3) 0.0746(11) Uani 0.50 6 d SP . . I2B I 0.0000 0.0000 0.3242(3) 0.0743(10) Uani 0.50 6 d SP . . C1 C 0.3333 0.6667 -0.9135(6) 0.0527(14) Uani 1 6 d S . . N2 N 0.1227(5) 0.5614(3) -0.6429(3) 0.0567(7) Uani 1 2 d S . . H2A H 0.0539 0.6302 -0.6415 0.068 Uiso 0.50 1 calc PR . . H2B H 0.0539 0.4237 -0.6436 0.068 Uiso 0.50 1 calc PR . . N1 N 0.2277(3) 0.7723(3) -0.9136(3) 0.0710(10) Uani 1 2 d S . . H1A H 0.0900 0.7035 -0.9139 0.085 Uiso 0.50 1 calc PR . . H1B H 0.2965 0.9100 -0.9135 0.085 Uiso 0.50 1 calc PR . . C2 C 0.3333 0.6667 -0.6439(5) 0.0441(12) Uani 1 6 d S . . 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 I1 0.04605(13) 0.04605(13) 0.06486(19) 0.000 0.000 0.02302(6) I2A 0.0440(5) 0.0440(5) 0.136(3) 0.000 0.000 0.0220(3) I2B 0.0386(4) 0.0386(4) 0.146(3) 0.000 0.000 0.0193(2) C1 0.053(2) 0.053(2) 0.053(3) 0.000 0.000 0.0264(11) N2 0.0401(15) 0.0466(12) 0.0812(19) -0.0015(9) -0.0030(17) 0.0200(7) N1 0.0539(14) 0.0539(14) 0.112(3) 0.0052(9) -0.0052(9) 0.0317(17) C2 0.0452(18) 0.0452(18) 0.042(3) 0.000 0.000 0.0226(9) _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 I2A I2B 0.546(6) . ? C1 N1 1.320(4) . ? C1 N1 1.320(4) 2_665 ? C1 N1 1.320(4) 3_565 ? N2 C2 1.315(3) . ? C2 N2 1.315(3) 3_565 ? C2 N2 1.315(3) 2_665 ? 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 C1 N1 120.000(5) . 2_665 ? N1 C1 N1 120.000(5) . 3_565 ? N1 C1 N1 120.000(4) 2_665 3_565 ? N2 C2 N2 119.990(12) . 3_565 ? N2 C2 N2 119.990(13) . 2_665 ? N2 C2 N2 119.990(12) 3_565 2_665 ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 32.31 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.251 _refine_diff_density_min -0.377 _refine_diff_density_rms 0.056 data_gi_htp_360 _database_code_depnum_ccdc_archive 'CCDC 914581' #TrackingRef 'web_deposit_cif_file_8_MarekSzafranski_1358248656.gi_htp_360.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'guanidinium iodide' _chemical_melting_point 460(5) _chemical_formula_moiety ? _chemical_formula_sum 'C H6 I N3' _chemical_formula_weight 186.99 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' I I -0.4742 1.8119 '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)/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' _cell_length_a 5.23783(9) _cell_length_b 7.54922(14) _cell_length_c 6.98292(13) _cell_angle_alpha 90.00 _cell_angle_beta 96.7315(17) _cell_angle_gamma 90.00 _cell_volume 274.212(9) _cell_formula_units_Z 2 _cell_measurement_temperature 360.0(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.265 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 172 _exptl_absorpt_coefficient_mu 5.692 _exptl_absorpt_correction_T_min 0.70091 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'CrysalisPro (Oxford Diffraction 2010)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 360.0(1) _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 'Gemini A Ultra' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6886 _diffrn_reflns_av_R_equivalents 0.0246 _diffrn_reflns_av_sigmaI/netI 0.0110 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.94 _diffrn_reflns_theta_max 32.09 _reflns_number_total 999 _reflns_number_gt 909 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. 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^)+(0.0260P)^2^+0.1009P] 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 SHELXL _refine_ls_extinction_coef 0.347(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 999 _refine_ls_number_parameters 29 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0259 _refine_ls_R_factor_gt 0.0232 _refine_ls_wR_factor_ref 0.0583 _refine_ls_wR_factor_gt 0.0563 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.089 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.0826(6) 0.3974(5) 0.7131(4) 0.0959(10) Uani 1 1 d . . . H1A H 0.0163 0.4971 0.7407 0.115 Uiso 1 1 calc R . . H1B H 0.2179 0.3953 0.6542 0.115 Uiso 1 1 calc R . . C1 C -0.0215(7) 0.2500 0.7605(5) 0.0580(7) Uani 1 2 d S . . N2 N -0.2245(8) 0.2500 0.8490(6) 0.1067(17) Uani 1 2 d S . . H2A H -0.2930 0.1513 0.8775 0.128 Uiso 0.50 1 calc PR . . H2B H -0.2913 0.3487 0.8794 0.128 Uiso 0.50 1 calc PR . . I2 I 0.57419(4) 0.7500 0.72666(3) 0.07136(16) Uani 1 2 d S . . 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 0.099(2) 0.0799(19) 0.106(2) 0.0154(14) 0.0014(18) -0.0202(14) C1 0.0555(15) 0.0643(18) 0.0545(15) 0.000 0.0082(12) 0.000 N2 0.073(2) 0.173(5) 0.079(2) 0.000 0.0309(18) 0.000 I2 0.0724(2) 0.0702(2) 0.0754(2) 0.000 0.02525(12) 0.000 _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 N1 C1 1.299(4) . ? C1 N2 1.291(5) . ? C1 N1 1.299(4) 4_565 ? 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 N2 C1 N1 121.1(2) . 4_565 ? N2 C1 N1 121.1(2) . . ? N1 C1 N1 117.9(4) 4_565 . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 32.09 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.403 _refine_diff_density_min -0.489 _refine_diff_density_rms 0.083