# 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_global data_3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C3 H3 I3 N2' _chemical_formula_weight 447.77 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 orthorhombic _symmetry_space_group_name_H-M Pmmn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-x, y+1/2, -z' 'x+1/2, -y, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'x, -y-1/2, z' '-x-1/2, y, z' _cell_length_a 7.2366(3) _cell_length_b 8.4314(3) _cell_length_c 7.2292(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 441.09(3) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 1414 _cell_measurement_theta_min 3.73 _cell_measurement_theta_max 25.65 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.371 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 10.549 _exptl_absorpt_correction_T_min 0.55165 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 295(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 ? _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 1414 _diffrn_reflns_av_R_equivalents 0.0212 _diffrn_reflns_av_sigmaI/netI 0.0246 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 3.71 _diffrn_reflns_theta_max 25.65 _reflns_number_total 489 _reflns_number_gt 432 _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^)+(0.0250P)^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 489 _refine_ls_number_parameters 29 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0276 _refine_ls_R_factor_gt 0.0230 _refine_ls_wR_factor_ref 0.0514 _refine_ls_wR_factor_gt 0.0492 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.055 _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 0.2500 0.7500 0.96500(9) 0.0448(2) Uani 1 4 d S . . I2 I 0.2500 0.48988(5) 0.34955(6) 0.03800(18) Uani 1 2 d S . . N1 N 0.2500 0.3776(6) 0.7494(7) 0.0364(13) Uani 1 2 d SD . . H1 H 0.2500 0.477(3) 0.789(11) 0.044 Uiso 1 2 d SD . . C2 C 0.2500 0.2500 0.8553(13) 0.040(2) Uani 1 4 d S . . H2 H 0.2500 0.2500 0.9840 0.047 Uiso 1 4 calc SR . . C3 C 0.2500 0.3295(7) 0.5672(8) 0.0304(13) 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 I1 0.0743(4) 0.0252(3) 0.0350(4) 0.000 0.000 0.000 I2 0.0474(3) 0.0313(3) 0.0354(3) 0.00629(18) 0.000 0.000 N1 0.049(3) 0.028(3) 0.032(3) -0.003(3) 0.000 0.000 C2 0.052(5) 0.038(6) 0.028(5) 0.000 0.000 0.000 C3 0.035(3) 0.029(3) 0.027(3) 0.000(3) 0.000 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 I2 C3 2.075(6) . ? N1 C2 1.321(7) . ? N1 C3 1.378(8) . ? N1 H1 0.889(10) . ? C2 N1 1.321(7) 2 ? C2 H2 0.9300 . ? C3 C3 1.341(12) 2 ? 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 C3 108.3(6) . . ? C2 N1 H1 126(5) . . ? C3 N1 H1 126(5) . . ? N1 C2 N1 109.1(8) 2 . ? N1 C2 H2 125.5 2 . ? N1 C2 H2 125.5 . . ? C3 C3 N1 107.1(3) 2 . ? C3 C3 I2 130.66(16) 2 . ? N1 C3 I2 122.2(4) . . ? 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 N1 H1 I1 0.889(10) 2.627(19) 3.505(5) 170(7) . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.65 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.469 _refine_diff_density_min -0.988 _refine_diff_density_rms 0.142 _database_code_depnum_ccdc_archive 'CCDC 929449' ####################################################################### # # 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_global # Attachment 'C3N2H5I-110K.CIF' data_5 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C3 H5 I N2' _chemical_formula_weight 195.99 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)/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 7.8732(5) _cell_length_b 15.4592(7) _cell_length_c 9.6771(6) _cell_angle_alpha 90.00 _cell_angle_beta 106.647(6) _cell_angle_gamma 90.00 _cell_volume 1128.47(11) _cell_formula_units_Z 8 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 11100 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 25.68 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.307 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 5.534 _exptl_absorpt_correction_T_min 0.77653 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 110(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 ? _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 11100 _diffrn_reflns_av_R_equivalents 0.0923 _diffrn_reflns_av_sigmaI/netI 0.0478 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 25.68 _reflns_number_total 2123 _reflns_number_gt 1878 _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^)+(0.0700P)^2^+4.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2123 _refine_ls_number_parameters 109 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0683 _refine_ls_R_factor_gt 0.0624 _refine_ls_wR_factor_ref 0.1342 _refine_ls_wR_factor_gt 0.1320 _refine_ls_goodness_of_fit_ref 1.276 _refine_ls_restrained_S_all 1.276 _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 0.23838(7) 0.01081(4) 0.21078(6) 0.0175(2) Uani 1 1 d . . . I2 I 0.47291(8) 0.23997(4) 0.98632(5) 0.0188(2) Uani 1 1 d . . . N1 N 0.2816(11) 0.0376(6) 0.8369(9) 0.0263(18) Uani 1 1 d . . . H1 H 0.3086 0.0709 0.9112 0.032 Uiso 1 1 calc R . . N3 N 0.2273(11) -0.0757(6) 0.7094(10) 0.032(2) Uani 1 1 d . . . H3 H 0.2133 -0.1292 0.6843 0.038 Uiso 1 1 calc R . . C2 C 0.2454(12) 0.0651(8) 0.7002(11) 0.031(2) Uani 1 1 d . . . H2 H 0.2459 0.1220 0.6695 0.038 Uiso 1 1 calc R . . C4 C 0.2703(13) -0.0469(7) 0.8419(11) 0.027(2) Uani 1 1 d . . . H4 H 0.2894 -0.0803 0.9248 0.033 Uiso 1 1 calc R . . C5 C 0.2079(16) -0.0060(8) 0.6158(13) 0.041(3) Uani 1 1 d . . . H5 H 0.1758 -0.0078 0.5156 0.049 Uiso 1 1 calc R . . N6 N 0.0003(9) 0.1831(6) -0.0012(8) 0.0242(19) Uani 1 1 d . . . H6 H 0.0119 0.1294 0.0230 0.029 Uiso 1 1 calc R . . N8 N -0.0522(11) 0.2978(5) -0.1285(9) 0.0286(19) Uani 1 1 d . . . H8 H -0.0812 0.3315 -0.2022 0.034 Uiso 1 1 calc R . . C7 C -0.0467(13) 0.2125(6) -0.1338(10) 0.026(2) Uani 1 1 d . . . H7 H -0.0718 0.1791 -0.2171 0.031 Uiso 1 1 calc R . . C9 C 0.0277(16) 0.2511(8) 0.0924(11) 0.040(3) Uani 1 1 d . . . H9 H 0.0622 0.2478 0.1926 0.048 Uiso 1 1 calc R . . C10 C -0.0046(12) 0.3244(8) 0.0123(11) 0.032(3) Uani 1 1 d . . . H10 H 0.0037 0.3810 0.0460 0.039 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 I1 0.0204(3) 0.0145(3) 0.0164(3) 0.00040(19) 0.0035(2) -0.00062(19) I2 0.0245(3) 0.0142(3) 0.0182(3) 0.00084(19) 0.0071(2) 0.0000(2) N1 0.027(4) 0.024(4) 0.029(4) -0.012(4) 0.010(3) 0.001(4) N3 0.024(4) 0.021(5) 0.055(6) -0.016(4) 0.018(4) -0.008(3) C2 0.020(5) 0.029(6) 0.044(7) 0.014(5) 0.010(4) -0.004(4) C4 0.028(5) 0.030(5) 0.027(5) 0.004(4) 0.014(4) 0.004(4) C5 0.030(6) 0.075(10) 0.021(5) 0.003(5) 0.012(5) 0.007(5) N6 0.021(4) 0.020(4) 0.033(5) 0.012(3) 0.010(4) 0.004(3) N8 0.028(4) 0.020(4) 0.035(5) 0.012(3) 0.005(4) 0.001(3) C7 0.032(5) 0.027(5) 0.022(5) -0.007(4) 0.011(4) -0.006(4) C9 0.028(6) 0.074(9) 0.021(5) -0.007(6) 0.012(4) -0.004(5) C10 0.019(5) 0.028(6) 0.050(7) -0.019(5) 0.010(5) -0.003(4) _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 C4 1.311(15) . ? N1 C2 1.339(13) . ? N1 H1 0.8600 . ? N3 C4 1.307(13) . ? N3 C5 1.388(15) . ? N3 H3 0.8600 . ? C2 C5 1.350(16) . ? C2 H2 0.9300 . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? N6 C7 1.311(11) . ? N6 C9 1.364(14) . ? N6 H6 0.8600 . ? N8 C7 1.320(13) . ? N8 C10 1.368(12) . ? N8 H8 0.8600 . ? C7 H7 0.9300 . ? C9 C10 1.355(16) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 N1 C2 110.8(8) . . ? C4 N1 H1 124.6 . . ? C2 N1 H1 124.6 . . ? C4 N3 C5 108.9(9) . . ? C4 N3 H3 125.5 . . ? C5 N3 H3 125.5 . . ? C5 C2 N1 106.7(9) . . ? C5 C2 H2 126.7 . . ? N1 C2 H2 126.7 . . ? N1 C4 N3 107.7(9) . . ? N1 C4 H4 126.1 . . ? N3 C4 H4 126.1 . . ? C2 C5 N3 105.9(10) . . ? C2 C5 H5 127.1 . . ? N3 C5 H5 127.1 . . ? C7 N6 C9 109.2(9) . . ? C7 N6 H6 125.4 . . ? C9 N6 H6 125.4 . . ? C7 N8 C10 109.6(8) . . ? C7 N8 H8 125.2 . . ? C10 N8 H8 125.2 . . ? N8 C7 N6 108.2(8) . . ? N8 C7 H7 125.9 . . ? N6 C7 H7 125.9 . . ? C10 C9 N6 107.2(9) . . ? C10 C9 H9 126.4 . . ? N6 C9 H9 126.4 . . ? C9 C10 N8 105.8(9) . . ? C9 C10 H10 127.1 . . ? N8 C10 H10 127.1 . . ? 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 N1 H1 I2 0.86 2.91 3.591(8) 136.9 . N3 H3 I2 0.86 2.75 3.533(8) 151.5 2_546 N6 H6 I1 0.86 2.83 3.551(8) 143.1 . N8 H8 I1 0.86 2.83 3.525(8) 139.6 4_565 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 4.839 _refine_diff_density_min -1.538 _refine_diff_density_rms 0.474 _database_code_depnum_ccdc_archive 'CCDC 929450' ####################################################################### # # 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_global # Attachment 'C3N2H5I-295K.CIF' data_4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C3 H5 I N2' _chemical_formula_weight 195.99 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 trigonal _symmetry_space_group_name_H-M R-3m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'y, x, -z' 'x-y, -y, -z' '-x, -x+y, -z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'y+2/3, x+1/3, -z+1/3' 'x-y+2/3, -y+1/3, -z+1/3' '-x+2/3, -x+y+1/3, -z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' 'y+1/3, x+2/3, -z+2/3' 'x-y+1/3, -y+2/3, -z+2/3' '-x+1/3, -x+y+2/3, -z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-y, -x, z' '-x+y, y, z' 'x, x-y, z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-y+2/3, -x+1/3, z+1/3' '-x+y+2/3, y+1/3, z+1/3' 'x+2/3, x-y+1/3, z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' '-y+1/3, -x+2/3, z+2/3' '-x+y+1/3, y+2/3, z+2/3' 'x+1/3, x-y+2/3, z+2/3' _cell_length_a 7.8956(9) _cell_length_b 7.8956(9) _cell_length_c 8.0774(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 436.09(11) _cell_formula_units_Z 3 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 1677 _cell_measurement_theta_min 3.90 _cell_measurement_theta_max 25.66 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _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_000 270 _exptl_absorpt_coefficient_mu 5.371 _exptl_absorpt_correction_T_min 0.77653 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 295(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 ? _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 1677 _diffrn_reflns_av_R_equivalents 0.0221 _diffrn_reflns_av_sigmaI/netI 0.0088 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.90 _diffrn_reflns_theta_max 25.66 _reflns_number_total 118 _reflns_number_gt 118 _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^)+(0.0400P)^2^+0.7000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.104(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 118 _refine_ls_number_parameters 5 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0204 _refine_ls_R_factor_gt 0.0204 _refine_ls_wR_factor_ref 0.0547 _refine_ls_wR_factor_gt 0.0547 _refine_ls_goodness_of_fit_ref 0.975 _refine_ls_restrained_S_all 0.975 _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 I I 0.0000 0.0000 0.0000 0.0760(6) Uani 1 12 d S . . N1 N 0.3153 0.4928 0.1441 0.0500(14) Uiso 0.0833 1 d PR A -1 H1 H 0.2988 0.3772 0.1325 0.060 Uiso 0.0833 1 calc PR A -1 C2 C 0.4971 0.6673 0.1674 0.0500(14) Uiso 0.0833 2 d SPR A -1 H2 H 0.6192 0.6767 0.1726 0.060 Uiso 0.0833 1 calc PR A -1 C3 C 0.4598 0.8250 0.1811 0.0500(14) Uiso 0.0833 1 d PR A -1 H3 H 0.5531 0.9558 0.1969 0.060 Uiso 0.0833 1 calc PR A -1 N4 N 0.2549 0.7479 0.1663 0.0500(14) Uiso 0.0833 2 d SPR A -1 H4 H 0.1954 0.8140 0.1705 0.060 Uiso 0.0833 2 calc SPR A -1 C5 C 0.1656 0.5426 0.1435 0.0500(14) Uiso 0.0833 1 d PR A -1 H5 H 0.0325 0.4560 0.1304 0.060 Uiso 0.0833 1 calc PR A -1 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 I 0.0726(6) 0.0726(6) 0.0829(8) 0.000 0.000 0.0363(3) _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 C5 1.4200 . ? N1 C2 1.4200 . ? C2 C3 1.4200 . ? C3 N4 1.4200 . ? N4 C5 1.4200 . ? 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 C5 N1 C2 108.0 . . ? C3 C2 N1 108.0 . . ? C2 C3 N4 108.0 . . ? C5 N4 C3 108.0 . . ? N1 C5 N4 108.0 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.66 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.577 _refine_diff_density_min -0.336 _refine_diff_density_rms 0.070 _database_code_depnum_ccdc_archive 'CCDC 929451' ####################################################################### # # 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_global # Attachment 'C12H20I8N8_115K.CIF' data_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C48 H80 I32 N32' _chemical_formula_weight 5166.24 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' 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 13.9633(16) _cell_length_b 15.6595(10) _cell_length_c 14.9399(13) _cell_angle_alpha 90.00 _cell_angle_beta 116.778(7) _cell_angle_gamma 90.00 _cell_volume 2916.4(5) _cell_formula_units_Z 1 _cell_measurement_temperature 115(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.942 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2288 _exptl_absorpt_coefficient_mu 8.524 _exptl_absorpt_correction_T_min 0.86016 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET) (compiled May 29 2009,17:40:42) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 115(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 ? _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 17335 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0247 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 25.68 _reflns_number_total 17352 _reflns_number_gt 14614 _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^)+(0.0700P)^2^+4.0000P] 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 SHELXL _refine_ls_extinction_coef 0.000087(17) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 17352 _refine_ls_number_parameters 115 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0581 _refine_ls_R_factor_gt 0.0463 _refine_ls_wR_factor_ref 0.1289 _refine_ls_wR_factor_gt 0.1224 _refine_ls_goodness_of_fit_ref 1.201 _refine_ls_restrained_S_all 1.201 _refine_ls_shift/su_max 0.002 _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 -0.76124(2) -0.114143(19) 0.42669(2) 0.01593(9) Uani 1 1 d . . . I2 I -0.08474(2) -0.11928(2) 0.41642(2) 0.01831(9) Uani 1 1 d . . . I3 I -0.51388(2) -0.12055(2) 0.41869(2) 0.02342(9) Uani 1 1 d . . . I4 I -0.31465(2) -0.12541(2) 0.41567(2) 0.02227(9) Uani 1 1 d . . . N6 N -0.5544(3) -0.1115(3) 0.6744(3) 0.0268(10) Uani 1 1 d . . . H6 H -0.5973 -0.0923 0.6160 0.032 Uiso 1 1 calc R . . C7 C -0.5000 -0.0632(4) 0.7500 0.0204(14) Uani 1 2 d S . . H7 H -0.5000 -0.0039 0.7500 0.025 Uiso 1 2 calc SR . . C8 C -0.53685(14) -0.19660(13) 0.69642(16) 0.0313(12) Uani 1 1 d . . . H8 H -0.5649 -0.2431 0.6537 0.038 Uiso 1 1 calc R . . N1 N -0.80715(14) 0.09060(13) 0.17382(16) 0.0365(11) Uani 1 1 d R . . H1 H -0.8420 0.0492 0.1350 0.044 Uiso 1 1 calc R . . C2 C -0.81485(14) 0.17160(13) 0.14502(16) 0.0270(11) Uani 1 1 d R . . H2 H -0.8527 0.1935 0.0806 0.032 Uiso 1 1 calc R . . N3 N -0.75662(14) 0.21417(13) 0.22866(16) 0.0237(9) Uani 1 1 d R . . H3 H -0.7523 0.2689 0.2334 0.028 Uiso 1 1 calc R . . C4 C -0.73785(14) 0.08150(13) 0.27142(16) 0.0350(13) Uani 1 1 d R . . H4 H -0.7153 0.0322 0.3100 0.042 Uiso 1 1 calc R . . C5 C -0.70975(14) 0.16460(13) 0.29832(16) 0.0300(12) Uani 1 1 d R . . H5 H -0.6606 0.1816 0.3623 0.036 Uiso 1 1 calc R . . N9 N -0.4497(3) -0.5652(3) 0.8279(3) 0.0268(9) Uani 1 1 d . . . H9 H -0.4108 -0.5474 0.8880 0.032 Uiso 1 1 calc R . . C10 C -0.4686(3) -0.6500(4) 0.7985(4) 0.0321(12) Uani 1 1 d . . . H10 H -0.4421 -0.6976 0.8396 0.038 Uiso 1 1 calc R . . C11 C -0.5000 -0.5167(4) 0.7500 0.0188(13) Uani 1 2 d S . . H11 H -0.5000 -0.4574 0.7500 0.023 Uiso 1 2 calc SR . . 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 0.01777(14) 0.01300(18) 0.01417(15) -0.00019(12) 0.00468(11) 0.00104(11) I2 0.02124(15) 0.0154(2) 0.01688(16) 0.00120(12) 0.00736(12) 0.00026(11) I3 0.03043(16) 0.0159(2) 0.01813(17) 0.00142(12) 0.00576(13) -0.00040(13) I4 0.03298(16) 0.01266(19) 0.01561(16) -0.00080(11) 0.00602(13) -0.00071(12) N6 0.0132(16) 0.038(3) 0.026(2) -0.0053(19) 0.0062(16) 0.0014(17) C7 0.027(3) 0.017(4) 0.017(3) 0.000 0.008(3) 0.000 C8 0.027(2) 0.026(3) 0.051(3) -0.018(2) 0.027(2) -0.012(2) N1 0.024(2) 0.041(3) 0.051(3) -0.024(2) 0.022(2) -0.0160(19) C2 0.023(2) 0.038(3) 0.023(3) 0.003(2) 0.014(2) 0.003(2) N3 0.0211(19) 0.015(2) 0.031(2) 0.0031(18) 0.0089(18) 0.0020(16) C4 0.035(3) 0.024(3) 0.054(4) 0.023(3) 0.028(3) 0.011(2) C5 0.018(2) 0.037(4) 0.028(3) 0.005(2) 0.005(2) 0.005(2) N9 0.027(2) 0.032(3) 0.0153(19) -0.0048(18) 0.0038(17) 0.0019(18) C10 0.027(3) 0.020(3) 0.053(3) 0.012(2) 0.022(2) 0.012(2) C11 0.021(3) 0.015(4) 0.021(3) 0.000 0.011(3) 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 I3 I4 2.8036(5) . ? N6 C7 1.285(5) . ? N6 C8 1.368(5) . ? N6 H6 0.8600 . ? C7 N6 1.285(5) 2_456 ? C7 H7 0.9300 . ? C8 C8 1.462(4) 2_456 ? C8 H8 0.9300 . ? N1 C2 1.3281 . ? N1 C4 1.3459 . ? N1 H1 0.8600 . ? C2 N3 1.3234 . ? C2 H2 0.9300 . ? N3 C5 1.2249 . ? N3 H3 0.8600 . ? C4 C5 1.3663 . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? N9 C11 1.298(5) . ? N9 C10 1.386(7) . ? N9 H9 0.8600 . ? C10 C10 1.314(10) 2_456 ? C10 H10 0.9300 . ? C11 N9 1.298(5) 2_456 ? C11 H11 0.9300 . ? 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 C7 N6 C8 113.0(4) . . ? C7 N6 H6 123.5 . . ? C8 N6 H6 123.5 . . ? N6 C7 N6 107.9(6) . 2_456 ? N6 C7 H7 126.0 . . ? N6 C7 H7 126.0 2_456 . ? N6 C8 C8 103.00(19) . 2_456 ? N6 C8 H8 128.5 . . ? C8 C8 H8 128.5 2_456 . ? C2 N1 C4 111.5 . . ? C2 N1 H1 124.3 . . ? C4 N1 H1 124.3 . . ? N3 C2 N1 104.5 . . ? N3 C2 H2 127.8 . . ? N1 C2 H2 127.8 . . ? C5 N3 C2 110.4 . . ? C5 N3 H3 124.8 . . ? C2 N3 H3 124.8 . . ? N1 C4 C5 100.9 . . ? N1 C4 H4 129.6 . . ? C5 C4 H4 129.6 . . ? N3 C5 C4 112.4 . . ? N3 C5 H5 123.8 . . ? C4 C5 H5 123.8 . . ? C11 N9 C10 109.1(4) . . ? C11 N9 H9 125.5 . . ? C10 N9 H9 125.5 . . ? C10 C10 N9 106.7(3) 2_456 . ? C10 C10 H10 126.7 2_456 . ? N9 C10 H10 126.7 . . ? N9 C11 N9 108.6(6) . 2_456 ? N9 C11 H11 125.7 . . ? N9 C11 H11 125.7 2_456 . ? 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 N6 H6 I1 0.86 2.74 3.522(4) 151.5 . N1 H1 I2 0.86 2.81 3.614(2) 156.7 2_455 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.294 _refine_diff_density_min -2.262 _refine_diff_density_rms 0.249 _database_code_depnum_ccdc_archive 'CCDC 929452' ####################################################################### # # 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_global # Attachment 'C12H20I8N8_295K.CIF' data_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H20 I8 N8' _chemical_formula_weight 1291.56 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 orthorhombic _symmetry_space_group_name_H-M Fddd loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+3/4, -y+3/4, z' '-x+3/4, y, -z+3/4' 'x, -y+3/4, -z+3/4' 'x, y+1/2, z+1/2' '-x+3/4, -y+5/4, z+1/2' '-x+3/4, y+1/2, -z+5/4' 'x, -y+5/4, -z+5/4' 'x+1/2, y, z+1/2' '-x+5/4, -y+3/4, z+1/2' '-x+5/4, y, -z+5/4' 'x+1/2, -y+3/4, -z+5/4' 'x+1/2, y+1/2, z' '-x+5/4, -y+5/4, z' '-x+5/4, y+1/2, -z+3/4' 'x+1/2, -y+5/4, -z+3/4' '-x, -y, -z' 'x-3/4, y-3/4, -z' 'x-3/4, -y, z-3/4' '-x, y-3/4, z-3/4' '-x, -y+1/2, -z+1/2' 'x-3/4, y-1/4, -z+1/2' 'x-3/4, -y+1/2, z-1/4' '-x, y-1/4, z-1/4' '-x+1/2, -y, -z+1/2' 'x-1/4, y-3/4, -z+1/2' 'x-1/4, -y, z-1/4' '-x+1/2, y-3/4, z-1/4' '-x+1/2, -y+1/2, -z' 'x-1/4, y-1/4, -z' 'x-1/4, -y+1/2, z-3/4' '-x+1/2, y-1/4, z-3/4' _cell_length_a 14.1543(12) _cell_length_b 15.7359(10) _cell_length_c 27.1076(17) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 6037.7(7) _cell_formula_units_Z 8 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.97 _cell_measurement_theta_max 29.81 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.842 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4576 _exptl_absorpt_coefficient_mu 8.235 _exptl_absorpt_correction_T_min 0.86016 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET) (compiled May 29 2009,17:40:42) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 295(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 ? _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 17210 _diffrn_reflns_av_R_equivalents 0.0514 _diffrn_reflns_av_sigmaI/netI 0.0456 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 29.81 _reflns_number_total 2088 _reflns_number_gt 894 _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^)+(0.0550P)^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 SHELXL _refine_ls_extinction_coef 0.000017(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2088 _refine_ls_number_parameters 49 _refine_ls_number_restraints 13 _refine_ls_R_factor_all 0.1018 _refine_ls_R_factor_gt 0.0343 _refine_ls_wR_factor_ref 0.1057 _refine_ls_wR_factor_gt 0.0869 _refine_ls_goodness_of_fit_ref 0.834 _refine_ls_restrained_S_all 0.838 _refine_ls_shift/su_max 0.019 _refine_ls_shift/su_mean 0.002 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 0.96544(3) 0.12225(3) 0.210246(14) 0.06204(13) Uani 1 1 d . . . I2 I 0.72425(4) 0.12223(4) 0.206986(16) 0.07993(17) Uani 1 1 d . . . C5 C 0.8769(11) 0.3482(5) 0.1746(3) 0.060 Uiso 0.50 1 d PD . 1 H5 H 0.8825 0.3299 0.2071 0.072 Uiso 0.50 1 calc PR . 1 N1 N 0.8642(9) 0.4268(6) 0.1603(3) 0.070 Uiso 0.50 1 d PD A 1 H1 H 0.8561 0.4705 0.1789 0.084 Uiso 0.50 1 calc PR A 1 C2 C 0.8662(11) 0.4254(6) 0.1127(3) 0.070 Uiso 0.50 1 d PD A 1 H2 H 0.8597 0.4738 0.0933 0.084 Uiso 0.50 1 calc PR A 1 N3 N 0.8788(9) 0.3458(4) 0.0938(3) 0.060 Uiso 0.50 1 d PD A 1 H3 H 0.8842 0.3303 0.0635 0.072 Uiso 0.50 1 calc PR A 1 C4 C 0.8804(12) 0.2983(6) 0.1346(3) 0.070 Uiso 0.50 1 d PD . 1 H4 H 0.8836 0.2393 0.1352 0.084 Uiso 0.50 1 calc PR . 1 C6 C 0.8750 0.0779(2) 0.3750 0.070 Uiso 0.50 2 d SPD . 2 H6 H 0.8750 0.0187 0.3750 0.084 Uiso 0.50 2 calc SPR . 2 N7 N 0.8794(8) 0.12479(11) 0.33473(9) 0.060 Uiso 0.50 1 d PD . 2 H7 H 0.8826 0.1075 0.3047 0.072 Uiso 0.50 1 calc PR . 2 C8 C 0.8778(8) 0.20404(15) 0.35069(3) 0.070 Uiso 0.50 1 d PD . 2 H8 H 0.8802 0.2522 0.3309 0.084 Uiso 0.50 1 calc PR . 2 C9 C 0.8750 0.2329(2) 0.3750 0.070 Uiso 0.50 2 d SPD B 2 H9 H 0.8692 0.2807 0.3950 0.084 Uiso 0.25 1 calc PR B 2 N10 N 0.8851(7) 0.18369(11) 0.33593(10) 0.060 Uiso 0.50 1 d PD B 2 H10 H 0.8915 0.2005 0.3059 0.072 Uiso 0.50 1 calc PR B 2 C11 C 0.8837(3) 0.10396(15) 0.35109(4) 0.070 Uiso 0.50 1 d PD . 2 H11 H 0.8934 0.0562 0.3315 0.084 Uiso 0.50 1 calc PR . 2 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 0.0758(3) 0.0560(2) 0.0543(2) 0.0008(2) 0.0021(2) 0.0015(3) I2 0.1400(4) 0.0487(2) 0.0511(2) -0.0018(2) 0.0063(3) 0.0017(3) _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 I2 I2 2.8110(12) 14_545 ? C5 N1 1.309(7) . ? C5 C4 1.339(8) . ? C5 C4 1.959(13) 2_655 ? N1 C2 1.292(8) . ? C2 N3 1.366(7) . ? N3 C4 1.336(8) . ? C4 C5 1.959(13) 2_655 ? C6 N7 1.3196(10) 3_655 ? C6 N7 1.3196(10) . ? N7 C8 1.3202(10) . ? N7 C11 1.780(3) 3_655 ? C8 C8 1.3202(10) 3_655 ? C8 N10 1.757(3) 3_655 ? C8 C11 2.053(3) 3_655 ? C9 N10 1.3201(10) . ? C9 C11 2.134(4) . ? N10 C11 1.3203(10) . ? C11 C11 1.3200(10) 3_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 C5 C4 108.7(9) . . ? N1 C5 C4 16.9(6) . 2_655 ? C4 C5 C4 92.3(8) . 2_655 ? C2 N1 C5 106.0(10) . . ? N1 C2 N3 113.2(10) . . ? C4 N3 C2 101.7(8) . . ? C5 C4 N3 110.1(9) . . ? C5 C4 C5 20.5(4) . 2_655 ? N3 C4 C5 89.6(7) . 2_655 ? N7 C6 N7 111.9(3) 3_655 . ? C6 N7 C8 104.9(3) . . ? C6 N7 C11 23.57(17) . 3_655 ? C8 N7 C11 81.47(17) . 3_655 ? N7 C8 C8 109.16(11) . 3_655 ? N7 C8 N10 98.64(19) . 3_655 ? C8 C8 N10 10.8(2) 3_655 3_655 ? N7 C8 C11 59.04(15) . 3_655 ? C8 C8 C11 50.19(8) 3_655 3_655 ? N10 C8 C11 39.60(5) 3_655 3_655 ? N10 C9 C11 36.07(14) . . ? C9 N10 C11 107.9(3) . . ? N10 C11 C11 107.96(13) . 3_655 ? N10 C11 C9 36.06(15) . . ? C11 C11 C9 71.99(4) 3_655 . ? _diffrn_measured_fraction_theta_max 0.962 _diffrn_reflns_theta_full 29.81 _diffrn_measured_fraction_theta_full 0.962 _refine_diff_density_max 0.968 _refine_diff_density_min -0.945 _refine_diff_density_rms 0.152 _database_code_depnum_ccdc_archive 'CCDC 929453'