# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Prof. L Brammer' _publ_contact_author_email lee.brammer@sheffield.ac.uk _publ_section_title ; Diiodoacetylene: compact, strong ditopic halogen bond donor ; loop_ _publ_author_name Brammer C.Perkins S.Libri H.Adams # Attachment '- C2I2adducts.cif' # Data for compounds 1-4 in "Diiodoacetylene: compact, strong # ditopic halogen bond donor," by Catherine Perkins, # Stefano Libri, Harry Adams and Lee Brammer* # C2I2.DMF (compound 1) data_ilb1217m _database_code_depnum_ccdc_archive 'CCDC 865218' #TrackingRef '- C2I2adducts.cif' _audit_creation_date 2011-10-25 _audit_creation_method ; Olex2 1.1-alpha (compiled 2011.09.28 svn.r2007, GUI svn.r3868) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C3 H7 N O, C2 I2' _chemical_formula_sum 'C5 H7 I2 N O' _chemical_formula_weight 350.92 _chemical_melting_point ? 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/n 1' _space_group_name_Hall '-P 2yn' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x-1/2, -y-1/2, z-1/2' _cell_length_a 5.575(3) _cell_length_b 14.420(7) _cell_length_c 11.901(6) _cell_angle_alpha 90.00 _cell_angle_beta 103.109(8) _cell_angle_gamma 90.00 _cell_volume 931.8(8) _cell_formula_units_Z 4 _cell_measurement_reflns_used ? _cell_measurement_temperature 120 _cell_measurement_theta_max ? _cell_measurement_theta_min ? _exptl_absorpt_coefficient_mu 6.686 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_correction_T_min 0.286776 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2004/1 (Bruker,2004) was used for absorption correction. R(int) was 0.4717 before and 0.0344 after correction. The Ratio of minimum to maximum transmission is 0.2868. The \l/2 correction factor is 0.0015. ; _exptl_crystal_colour yellow _exptl_crystal_colour_modifier yellow _exptl_crystal_density_diffrn 2.501 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 632 _exptl_crystal_size_max 0.015 _exptl_crystal_size_mid 0.01 _exptl_crystal_size_min 0.008 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0369 _diffrn_reflns_av_unetI/netI 0.0367 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 5749 _diffrn_reflns_theta_full 25.68 _diffrn_reflns_theta_max 25.68 _diffrn_reflns_theta_min 3.33 _diffrn_ambient_temperature 120 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.976 _diffrn_measured_fraction_theta_max 0.976 _diffrn_measurement_device_type 'Bruker APEX II CCD detector' _diffrn_measurement_method 'omega and phi scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 1473 _reflns_number_total 1726 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'Bruker APEX II' _computing_data_collection 'Bruker APEX II' _computing_data_reduction 'Bruker APEX II' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _refine_diff_density_max 1.242 _refine_diff_density_min -1.155 _refine_diff_density_rms 0.225 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 84 _refine_ls_number_reflns 1726 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0408 _refine_ls_R_factor_gt 0.0304 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0572P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0785 _refine_ls_wR_factor_ref 0.0864 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 1.0473(8) 0.7671(3) 0.5539(4) 0.0311(10) Uani 1 1 d . . . N1 N 0.7037(8) 0.7085(3) 0.4338(4) 0.0244(10) Uani 1 1 d . . . C3 C 0.8467(11) 0.7759(4) 0.4859(5) 0.0259(13) Uani 1 1 d . . . H3 H 0.7889 0.8374 0.4691 0.031 Uiso 1 1 calc R . . C4 C 0.4705(12) 0.7259(5) 0.3554(6) 0.0376(15) Uani 1 1 d . . . H4A H 0.4358 0.7926 0.3529 0.056 Uiso 1 1 calc R . . H4B H 0.3401 0.6927 0.3818 0.056 Uiso 1 1 calc R . . H4C H 0.4769 0.7042 0.2781 0.056 Uiso 1 1 calc R . . C5 C 0.7831(12) 0.6115(4) 0.4547(6) 0.0323(14) Uani 1 1 d . . . H5A H 0.9040 0.5966 0.4091 0.048 Uiso 1 1 calc R . . H5B H 0.6402 0.5704 0.4321 0.048 Uiso 1 1 calc R . . H5C H 0.8580 0.6029 0.5369 0.048 Uiso 1 1 calc R . . I1 I 1.38583(7) 0.91300(2) 0.62976(3) 0.02601(15) Uani 1 1 d . . . I2 I 2.10056(6) 1.13713(2) 0.81787(3) 0.02612(15) Uani 1 1 d . . . C1 C 1.6598(10) 1.0009(4) 0.6995(5) 0.0256(12) Uani 1 1 d . . . C2 C 1.8268(10) 1.0502(4) 0.7412(5) 0.0265(12) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.032(2) 0.023(2) 0.034(2) -0.0045(18) 0.000(2) -0.0015(17) N1 0.027(2) 0.024(2) 0.021(2) 0.0013(19) 0.003(2) 0.0008(19) C3 0.032(3) 0.027(3) 0.020(3) 0.000(2) 0.008(3) 0.004(2) C4 0.035(4) 0.043(4) 0.029(4) 0.003(3) -0.005(3) 0.001(3) C5 0.041(3) 0.027(3) 0.025(3) 0.000(3) 0.001(3) 0.001(3) I1 0.0293(2) 0.0238(2) 0.0239(2) -0.00348(14) 0.00390(18) -0.00284(15) I2 0.0281(2) 0.0233(2) 0.0256(3) -0.00029(14) 0.00334(18) -0.00314(14) C1 0.032(3) 0.021(3) 0.022(3) -0.002(2) 0.003(3) -0.002(2) C2 0.026(3) 0.032(3) 0.019(3) 0.001(3) -0.002(2) 0.001(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 O1 C3 1.229(7) . ? N1 C3 1.319(8) . ? N1 C4 1.440(8) . ? N1 C5 1.471(8) . ? C3 H3 0.9500 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? I1 C1 2.013(6) . ? I2 C2 2.025(6) . ? C1 C2 1.187(8) . ? 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 C3 N1 C4 122.4(5) . . ? C3 N1 C5 119.6(5) . . ? C4 N1 C5 117.9(5) . . ? O1 C3 N1 126.6(5) . . ? O1 C3 H3 116.7 . . ? N1 C3 H3 116.7 . . ? N1 C4 H4A 109.5 . . ? N1 C4 H4B 109.5 . . ? N1 C4 H4C 109.5 . . ? H4A C4 H4B 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N1 C5 H5A 109.5 . . ? N1 C5 H5B 109.5 . . ? N1 C5 H5C 109.5 . . ? H5A C5 H5B 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C2 C1 I1 177.8(5) . . ? C1 C2 I2 177.0(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 N1 C3 O1 179.8(6) . . . . ? C5 N1 C3 O1 -0.7(9) . . . . ? # END # C2I2.pyrazine (compound 2) data_ilb1301_0m _database_code_depnum_ccdc_archive 'CCDC 865219' #TrackingRef '- C2I2adducts.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C4 H4 N2, C2 I2' _chemical_formula_sum 'C6 H4 I2 N2' _chemical_formula_weight 357.91 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' I I -0.4742 1.8119 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 4.2383(6) _cell_length_b 7.3655(10) _cell_length_c 7.8486(10) _cell_angle_alpha 113.047(4) _cell_angle_beta 99.614(4) _cell_angle_gamma 93.365(4) _cell_volume 220.20(5) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3122 _cell_measurement_theta_min 2.88 _cell_measurement_theta_max 27.49 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.699 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 160 _exptl_absorpt_coefficient_mu 7.071 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ; Correction conducted using SADABS Ratio of minimum to maximum apparent transmission: 0.577675 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3429 _diffrn_reflns_av_R_equivalents 0.0216 _diffrn_reflns_av_sigmaI/netI 0.0208 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.88 _diffrn_reflns_theta_max 27.49 _reflns_number_total 1004 _reflns_number_gt 977 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX II' _computing_cell_refinement 'Bruker APEX II' _computing_data_reduction 'Bruker APEX II' _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^)+(0.1000P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1004 _refine_ls_number_parameters 46 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0408 _refine_ls_R_factor_gt 0.0401 _refine_ls_wR_factor_ref 0.1307 _refine_ls_wR_factor_gt 0.1300 _refine_ls_goodness_of_fit_ref 1.234 _refine_ls_restrained_S_all 1.234 _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 0.82947(8) 0.28716(5) 0.67842(5) 0.0221(3) Uani 1 1 d . . . C1 C 0.9608(18) 0.4511(10) 0.5414(10) 0.0232(13) Uani 1 1 d . . . N1 N 0.6262(16) 0.0845(10) 0.8907(10) 0.0272(13) Uani 1 1 d . . . C2 C 0.6109(15) -0.1123(9) 0.8488(8) 0.0253(12) Uani 1 1 d . . . H2 H 0.6834 -0.1955 0.7433 0.030 Uiso 1 1 calc R . . C3 C 0.4886(18) -0.1904(10) 0.9612(11) 0.0305(15) Uani 1 1 d . . . H3 H 0.4872 -0.3259 0.9304 0.037 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 0.0239(3) 0.0226(3) 0.0252(4) 0.0145(3) 0.0077(2) 0.0029(2) C1 0.032(3) 0.017(3) 0.021(3) 0.007(2) 0.009(2) 0.003(2) N1 0.027(3) 0.029(3) 0.029(3) 0.015(3) 0.006(2) -0.002(2) C2 0.034(3) 0.026(3) 0.018(3) 0.009(2) 0.007(2) 0.008(2) C3 0.041(3) 0.020(3) 0.028(3) 0.007(3) 0.005(3) 0.007(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 I1 C1 2.015(7) . ? C1 C1 1.210(14) 2_766 ? N1 C2 1.350(9) . ? N1 C3 1.311(11) 2_657 ? C2 C3 1.376(10) . ? C2 H2 0.9300 . ? C3 H3 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 C1 C1 I1 179.7(9) 2_766 . ? C3 N1 C2 115.9(7) 2_657 . ? N1 C2 C3 120.3(6) . . ? N1 C2 H2 119.8 . . ? C3 C2 H2 119.8 . . ? N1 C3 C2 123.7(7) 2_657 . ? N1 C3 H3 118.2 2_657 . ? C2 C3 H3 118.2 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 N1 C2 C3 -1.7(11) 2_657 . . . ? N1 C2 C3 N1 1.8(12) . . . 2_657 ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 4.043 _refine_diff_density_min -1.118 _refine_diff_density_rms 0.441 # END # C2I2.dabco (compound 3) data_ilb1310_p21m _database_code_depnum_ccdc_archive 'CCDC 865220' #TrackingRef '- C2I2adducts.cif' _audit_creation_date 2011-10-25 _audit_creation_method ; Olex2 1.1-alpha (compiled 2011.09.28 svn.r2007, GUI svn.r3868) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety '0.5(C4 I4), C6 H12 N2' _chemical_formula_sum 'C8 H12 I2 N2' _chemical_formula_weight 390.00 _chemical_melting_point ? 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' I I -0.4742 1.8119 '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' _space_group_crystal_system monoclinic _space_group_IT_number 11 _space_group_name_H-M_alt 'P 1 21/m 1' _space_group_name_Hall '-P 2yb' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z' 3 '-x, -y, -z' 4 'x, -y-1/2, z' _cell_length_a 6.5418(2) _cell_length_b 8.2834(3) _cell_length_c 10.3370(3) _cell_angle_alpha 90.00 _cell_angle_beta 101.233(2) _cell_angle_gamma 90.00 _cell_volume 549.41(3) _cell_formula_units_Z 2 _cell_measurement_reflns_used ? _cell_measurement_temperature 120 _cell_measurement_theta_max ? _cell_measurement_theta_min ? _exptl_absorpt_coefficient_mu 5.678 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_correction_T_min 0.751487 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2004/1 (Bruker,2004) was used for absorption correction. R(int) was 0.0478 before and 0.0212 after correction. The Ratio of minimum to maximum transmission is 0.7515. The \l/2 correction factor is 0.0015. ; _exptl_crystal_colour yellow _exptl_crystal_colour_modifier yellow _exptl_crystal_density_diffrn 2.357 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 360 _exptl_crystal_size_max 0.03 _exptl_crystal_size_mid 0.021 _exptl_crystal_size_min 0.012 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0236 _diffrn_reflns_av_unetI/netI 0.0237 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 4640 _diffrn_reflns_theta_full 27.49 _diffrn_reflns_theta_max 27.49 _diffrn_reflns_theta_min 3.18 _diffrn_ambient_temperature 120 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Bruker APEX II CCD detector' _diffrn_measurement_method 'omega and phi scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 1121 _reflns_number_total 1345 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'Bruker APEX II' _computing_data_collection 'Bruker APEX II' _computing_data_reduction 'Bruker APEX II' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; XS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.443 _refine_diff_density_min -0.534 _refine_diff_density_rms 0.108 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 67 _refine_ls_number_reflns 1345 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0268 _refine_ls_R_factor_gt 0.0184 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0212P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0390 _refine_ls_wR_factor_ref 0.0433 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.27528(4) 0.7500 0.43097(2) 0.02112(9) Uani 1 2 d S . . I2 I 0.65340(4) 0.7500 0.02467(2) 0.02102(9) Uani 1 2 d S . . C2 C 0.4918(8) 0.7500 0.1749(5) 0.0285(10) Uani 1 2 d S . . C1 C 0.4100(8) 0.7500 0.2691(4) 0.0278(10) Uani 1 2 d S . . N1 N 1.0870(6) 0.7500 -0.3565(3) 0.0211(7) Uani 1 2 d S . . N2 N 0.8799(6) 0.7500 -0.1693(3) 0.0208(7) Uani 1 2 d S . . C5 C 0.8596(7) 0.7500 -0.4119(4) 0.0217(9) Uani 1 2 d S . . H5A H 0.8227 0.6532 -0.4678 0.026 Uiso 0.50 1 calc PR . . H5B H 0.8227 0.8468 -0.4678 0.026 Uiso 0.50 1 calc PR . . C4 C 1.0133(5) 0.8945(3) -0.1603(3) 0.0232(6) Uani 1 1 d . . . H4A H 1.1110 0.8958 -0.0741 0.028 Uiso 1 1 calc R . . H4B H 0.9258 0.9928 -0.1662 0.028 Uiso 1 1 calc R . . C6 C 0.7348(7) 0.7500 -0.2981(4) 0.0243(9) Uani 1 2 d S . . H6A H 0.6446 0.8468 -0.3053 0.029 Uiso 0.50 1 calc PR . . H6B H 0.6446 0.6532 -0.3053 0.029 Uiso 0.50 1 calc PR . . C3 C 1.1382(5) 0.8946(3) -0.2733(3) 0.0237(6) Uani 1 1 d . . . H3A H 1.1041 0.9929 -0.3278 0.028 Uiso 1 1 calc R . . H3B H 1.2894 0.8961 -0.2355 0.028 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 0.02199(16) 0.02499(14) 0.01859(15) 0.000 0.00943(11) 0.000 I2 0.02252(16) 0.02424(14) 0.01870(15) 0.000 0.00992(12) 0.000 C2 0.031(3) 0.030(2) 0.027(2) 0.000 0.013(2) 0.000 C1 0.027(3) 0.030(2) 0.029(2) 0.000 0.012(2) 0.000 N1 0.0216(19) 0.0241(16) 0.0194(18) 0.000 0.0085(15) 0.000 N2 0.0196(19) 0.0234(16) 0.0211(18) 0.000 0.0080(15) 0.000 C5 0.022(2) 0.027(2) 0.018(2) 0.000 0.0080(17) 0.000 C4 0.0267(17) 0.0224(14) 0.0224(15) -0.0021(12) 0.0093(13) -0.0016(13) C6 0.016(2) 0.038(2) 0.021(2) 0.000 0.0076(17) 0.000 C3 0.0238(16) 0.0237(14) 0.0257(16) -0.0022(12) 0.0103(13) -0.0017(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 C1 2.037(4) . ? I2 C2 2.042(5) . ? C2 C1 1.199(6) . ? N1 C5 1.487(6) . ? N1 C3 1.475(3) 4_575 ? N1 C3 1.475(3) . ? N2 C4 1.474(4) . ? N2 C4 1.474(4) 4_575 ? N2 C6 1.477(5) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C5 C6 1.557(6) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C4 C3 1.550(4) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 C2 I2 175.5(5) . . ? C2 C1 I1 179.1(5) . . ? C3 N1 C5 108.7(2) . . ? C3 N1 C5 108.7(2) 4_575 . ? C3 N1 C3 108.6(3) . 4_575 ? C4 N2 C4 108.6(3) . 4_575 ? C4 N2 C6 109.0(2) . . ? C4 N2 C6 109.0(2) 4_575 . ? N1 C5 H5A 109.7 . . ? N1 C5 H5B 109.7 . . ? N1 C5 C6 110.0(3) . . ? H5A C5 H5B 108.2 . . ? C6 C5 H5A 109.7 . . ? C6 C5 H5B 109.7 . . ? N2 C4 H4A 109.6 . . ? N2 C4 H4B 109.6 . . ? N2 C4 C3 110.2(2) . . ? H4A C4 H4B 108.1 . . ? C3 C4 H4A 109.6 . . ? C3 C4 H4B 109.6 . . ? N2 C6 C5 110.0(3) . . ? N2 C6 H6A 109.7 . . ? N2 C6 H6B 109.7 . . ? C5 C6 H6A 109.7 . . ? C5 C6 H6B 109.7 . . ? H6A C6 H6B 108.2 . . ? N1 C3 C4 110.3(2) . . ? N1 C3 H3A 109.6 . . ? N1 C3 H3B 109.6 . . ? C4 C3 H3A 109.6 . . ? C4 C3 H3B 109.6 . . ? H3A C3 H3B 108.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag I2 C2 C1 I1 0.00(3) . . . . ? N1 C5 C6 N2 0.0 . . . . ? N2 C4 C3 N1 -0.1(4) . . . . ? C5 N1 C3 C4 59.1(3) . . . . ? C4 N2 C4 C3 59.2(4) 4_575 . . . ? C4 N2 C6 C5 59.2(2) . . . . ? C4 N2 C6 C5 -59.2(2) 4_575 . . . ? C6 N2 C4 C3 -59.4(3) . . . . ? C3 N1 C5 C6 59.1(2) 4_575 . . . ? C3 N1 C5 C6 -59.1(2) . . . . ? C3 N1 C3 C4 -59.0(4) 4_575 . . . ? # END # C2I4.htma (compound 4) data_hmta _database_code_depnum_ccdc_archive 'CCDC 865221' #TrackingRef '- C2I2adducts.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C2 I4, C6 H12 N4' _chemical_formula_sum 'C8 H12 I4 N4' _chemical_formula_weight 671.82 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' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.9274(7) _cell_length_b 11.0145(4) _cell_length_c 8.7574(4) _cell_angle_alpha 90.00 _cell_angle_beta 92.800(2) _cell_angle_gamma 90.00 _cell_volume 1534.50(11) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.908 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 8.106 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1282 _exptl_absorpt_correction_T_max 0.3081 _exptl_absorpt_process_details SADABS _exptl_special_details ; ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15754 _diffrn_reflns_av_R_equivalents 0.0356 _diffrn_reflns_av_sigmaI/netI 0.0284 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 27.52 _reflns_number_total 3358 _reflns_number_gt 2595 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX II' _computing_cell_refinement 'Bruker APEX II' _computing_data_reduction 'Bruker APEX II' _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^)+(0.0122P)^2^+27.9266P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3358 _refine_ls_number_parameters 176 _refine_ls_number_restraints 51 _refine_ls_R_factor_all 0.0632 _refine_ls_R_factor_gt 0.0491 _refine_ls_wR_factor_ref 0.0952 _refine_ls_wR_factor_gt 0.0900 _refine_ls_goodness_of_fit_ref 1.191 _refine_ls_restrained_S_all 1.208 _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 0.90295(4) 0.83175(6) 0.89611(8) 0.02702(17) Uani 1 1 d . . . I2 I 0.89769(4) 1.15564(6) 0.88433(8) 0.02817(17) Uani 1 1 d . . . C8 C 0.9641(5) 0.9974(8) 0.9573(10) 0.0173(16) Uani 1 1 d . . . I3 I 0.60412(3) 0.49898(6) 0.28517(7) 0.02528(15) Uani 1 1 d D . . I4A I 0.52722(9) 0.72128(8) 0.54696(18) 0.0222(3) Uani 0.609(3) 1 d PDU A 1 I4B I 0.4918(9) 0.7274(2) 0.4802(16) 0.0243(6) Uani 0.154(8) 1 d PDU A 2 I4C I 0.4710(5) 0.7186(3) 0.4452(8) 0.0269(6) Uani 0.237(9) 1 d PDU A 3 C7 C 0.5220(4) 0.5400(6) 0.4627(7) 0.021(3) Uani 0.547(19) 1 d PDU . . C7' C 0.4793(4) 0.5414(6) 0.5399(7) 0.021(3) Uani 0.453(19) 1 d PDU . . N1 N 0.1979(5) 0.3969(8) 0.1444(11) 0.034(2) Uani 1 1 d . . . N2 N 0.2050(5) 0.6177(8) 0.1570(11) 0.032(2) Uani 1 1 d . . . N3 N 0.3000(5) 0.5066(8) -0.0058(9) 0.0250(17) Uani 1 1 d . . . N4 N 0.3188(4) 0.4944(7) 0.2736(8) 0.0223(16) Uani 1 1 d . . . C1 C 0.2504(7) 0.6195(11) 0.0146(13) 0.040(3) Uani 1 1 d . . . H1A H 0.2887 0.6902 0.0159 0.048 Uiso 1 1 calc R . . H1B H 0.2095 0.6291 -0.0733 0.048 Uiso 1 1 calc R . . C2 C 0.2428(7) 0.4033(12) 0.0009(13) 0.041(3) Uani 1 1 d . . . H2A H 0.2753 0.3275 -0.0106 0.050 Uiso 1 1 calc R . . H2B H 0.2010 0.4083 -0.0863 0.050 Uiso 1 1 calc R . . C3 C 0.1503(6) 0.5111(11) 0.1573(12) 0.036(3) Uani 1 1 d . . . H3A H 0.1081 0.5170 0.0708 0.043 Uiso 1 1 calc R . . H3B H 0.1198 0.5100 0.2532 0.043 Uiso 1 1 calc R . . C4 C 0.2684(7) 0.6052(9) 0.2862(12) 0.029(2) Uani 1 1 d . . . H4A H 0.3061 0.6767 0.2884 0.035 Uiso 1 1 calc R . . H4B H 0.2393 0.6034 0.3836 0.035 Uiso 1 1 calc R . . C5 C 0.2606(7) 0.3907(9) 0.2679(13) 0.031(2) Uani 1 1 d . . . H5A H 0.2934 0.3150 0.2577 0.037 Uiso 1 1 calc R . . H5B H 0.2322 0.3864 0.3658 0.037 Uiso 1 1 calc R . . C6 C 0.3603(5) 0.4993(8) 0.1276(11) 0.0224(18) Uani 1 1 d . . . H6A H 0.3956 0.4259 0.1179 0.027 Uiso 1 1 calc R . . H6B H 0.3979 0.5709 0.1277 0.027 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 0.0205(3) 0.0328(3) 0.0281(4) -0.0125(3) 0.0043(3) -0.0078(2) I2 0.0203(3) 0.0336(3) 0.0309(4) 0.0147(3) 0.0043(3) 0.0086(3) C8 0.017(4) 0.020(4) 0.015(4) 0.001(4) 0.002(3) 0.001(4) I3 0.0203(3) 0.0374(3) 0.0187(3) 0.0021(3) 0.0062(2) 0.0016(3) I4A 0.0256(6) 0.0113(4) 0.0308(7) -0.0024(4) 0.0109(5) -0.0039(4) I4B 0.0275(12) 0.0142(9) 0.0319(13) -0.0038(10) 0.0080(10) -0.0053(10) I4C 0.0304(10) 0.0181(8) 0.0326(11) -0.0032(9) 0.0054(9) -0.0041(8) C7 0.022(5) 0.020(4) 0.023(6) -0.004(5) 0.004(4) 0.003(5) C7' 0.022(5) 0.020(4) 0.022(6) -0.003(5) 0.004(4) 0.002(5) N1 0.030(5) 0.039(5) 0.034(6) -0.013(4) 0.011(4) -0.018(4) N2 0.024(4) 0.036(5) 0.036(6) 0.012(4) 0.011(4) 0.011(3) N3 0.022(4) 0.040(4) 0.013(4) -0.005(4) 0.005(3) -0.004(4) N4 0.020(4) 0.030(4) 0.017(4) -0.005(4) -0.003(3) 0.001(3) C1 0.033(6) 0.058(7) 0.029(7) 0.031(6) 0.012(5) 0.019(5) C2 0.034(6) 0.062(7) 0.029(7) -0.030(6) 0.011(5) -0.023(5) C3 0.014(4) 0.063(7) 0.031(6) -0.004(6) 0.005(4) -0.005(5) C4 0.042(6) 0.023(5) 0.023(6) -0.006(4) 0.012(5) 0.002(4) C5 0.037(6) 0.022(5) 0.034(7) 0.010(4) 0.014(5) 0.007(4) C6 0.018(4) 0.018(4) 0.032(5) -0.002(4) 0.002(3) 0.000(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 I1 C8 2.125(9) . ? I2 C8 2.121(9) . ? C8 C8 1.336(16) 3_777 ? I3 C7 2.129(5) . ? I3 C7' 2.124(5) 3_666 ? I4A C7 2.129(5) . ? I4A C7' 2.123(5) . ? I4B C7 2.127(5) . ? I4B C7' 2.126(5) . ? I4C C7 2.131(5) . ? I4C C7' 2.122(5) . ? C7 C7 1.318(18) 3_666 ? C7' C7' 1.341(18) 3_666 ? C7' I3 2.124(5) 3_666 ? N1 C5 1.438(14) . ? N1 C3 1.476(14) . ? N1 C2 1.478(13) . ? N2 C3 1.462(13) . ? N2 C1 1.472(13) . ? N2 C4 1.486(14) . ? N3 C2 1.460(13) . ? N3 C6 1.478(12) . ? N3 C1 1.488(13) . ? N4 C5 1.469(12) . ? N4 C6 1.469(11) . ? N4 C4 1.468(12) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 C8 I1 123.2(9) 3_777 . ? C8 C8 I2 122.3(9) 3_777 . ? I1 C8 I2 114.4(4) . . ? C7 C7 I4B 119.1(3) 3_666 . ? C7 C7 I4A 117.9(2) 3_666 . ? C7 C7 I3 125.5(3) 3_666 . ? I4B C7 I3 114.0(4) . . ? I4A C7 I3 115.9(4) . . ? C7 C7 I4C 116.3(3) 3_666 . ? I3 C7 I4C 112.9(4) . . ? C7' C7' I4A 117.7(3) 3_666 . ? C7' C7' I4C 116.4(3) 3_666 . ? C7' C7' I4B 118.2(2) 3_666 . ? C7' C7' I3 125.0(3) 3_666 3_666 ? I4A C7' I3 114.3(4) . 3_666 ? I4C C7' I3 116.4(4) . 3_666 ? I4B C7' I3 116.6(4) . 3_666 ? C5 N1 C3 108.9(8) . . ? C5 N1 C2 107.1(8) . . ? C3 N1 C2 107.2(9) . . ? C3 N2 C1 109.3(9) . . ? C3 N2 C4 107.9(8) . . ? C1 N2 C4 107.7(8) . . ? C2 N3 C6 108.0(8) . . ? C2 N3 C1 108.1(8) . . ? C6 N3 C1 106.2(8) . . ? C5 N4 C6 108.0(7) . . ? C5 N4 C4 107.6(7) . . ? C6 N4 C4 107.8(7) . . ? N2 C1 N3 112.1(8) . . ? N2 C1 H1A 109.2 . . ? N3 C1 H1A 109.2 . . ? N2 C1 H1B 109.2 . . ? N3 C1 H1B 109.2 . . ? H1A C1 H1B 107.9 . . ? N3 C2 N1 113.6(8) . . ? N3 C2 H2A 108.9 . . ? N1 C2 H2A 108.9 . . ? N3 C2 H2B 108.9 . . ? N1 C2 H2B 108.9 . . ? H2A C2 H2B 107.7 . . ? N2 C3 N1 112.0(7) . . ? N2 C3 H3A 109.2 . . ? N1 C3 H3A 109.2 . . ? N2 C3 H3B 109.2 . . ? N1 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? N4 C4 N2 111.9(8) . . ? N4 C4 H4A 109.2 . . ? N2 C4 H4A 109.2 . . ? N4 C4 H4B 109.2 . . ? N2 C4 H4B 109.2 . . ? H4A C4 H4B 107.9 . . ? N1 C5 N4 113.7(8) . . ? N1 C5 H5A 108.8 . . ? N4 C5 H5A 108.8 . . ? N1 C5 H5B 108.8 . . ? N4 C5 H5B 108.8 . . ? H5A C5 H5B 107.7 . . ? N4 C6 N3 112.7(7) . . ? N4 C6 H6A 109.0 . . ? N3 C6 H6A 109.0 . . ? N4 C6 H6B 109.0 . . ? N3 C6 H6B 109.0 . . ? H6A C6 H6B 107.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 N2 C1 N3 -57.2(12) . . . . ? C4 N2 C1 N3 59.7(12) . . . . ? C2 N3 C1 N2 55.9(12) . . . . ? C6 N3 C1 N2 -59.8(11) . . . . ? C6 N3 C2 N1 57.0(12) . . . . ? C1 N3 C2 N1 -57.5(12) . . . . ? C5 N1 C2 N3 -58.2(13) . . . . ? C3 N1 C2 N3 58.6(12) . . . . ? C1 N2 C3 N1 58.8(11) . . . . ? C4 N2 C3 N1 -57.9(10) . . . . ? C5 N1 C3 N2 57.3(11) . . . . ? C2 N1 C3 N2 -58.3(11) . . . . ? C5 N4 C4 N2 -57.9(10) . . . . ? C6 N4 C4 N2 58.4(10) . . . . ? C3 N2 C4 N4 59.1(10) . . . . ? C1 N2 C4 N4 -58.7(11) . . . . ? C3 N1 C5 N4 -57.2(10) . . . . ? C2 N1 C5 N4 58.5(11) . . . . ? C6 N4 C5 N1 -58.5(10) . . . . ? C4 N4 C5 N1 57.6(10) . . . . ? C5 N4 C6 N3 56.2(10) . . . . ? C4 N4 C6 N3 -59.8(10) . . . . ? C2 N3 C6 N4 -56.0(10) . . . . ? C1 N3 C6 N4 59.8(10) . . . . ? _diffrn_measured_fraction_theta_max 0.949 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.949 _refine_diff_density_max 2.610 _refine_diff_density_min -2.270 _refine_diff_density_rms 0.245 #END