# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Oleg Shishkin' _publ_contact_author_email SHISHKIN@XRAY.ISC.KHARKOV.COM _publ_section_title ; ; loop_ _publ_author_name 'Oleg Shishkin' 'Irina S Konovalova' 'Boris V Paponov' 'S V Shishkina' # Attachment 'DATm.CIF' data_experimental _database_code_depnum_ccdc_archive 'CCDC 735985' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C2 H5 N5' _chemical_formula_sum 'C2 H5 N5' _chemical_formula_weight 99.11 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.1601(5) _cell_length_b 5.9993(5) _cell_length_c 11.3396(8) _cell_angle_alpha 90.00 _cell_angle_beta 93.849(6) _cell_angle_gamma 90.00 _cell_volume 418.12(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1218 _cell_measurement_theta_min 3 _cell_measurement_theta_max 32 _exptl_crystal_description stick _exptl_crystal_colour red _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.574 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 208 _exptl_absorpt_coefficient_mu 0.119 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type Xcalibur"3 _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean 16.1827 _diffrn_standards_number 2 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8425 _diffrn_reflns_av_R_equivalents 0.0321 _diffrn_reflns_av_sigmaI/netI 0.0119 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.60 _diffrn_reflns_theta_max 29.99 _reflns_number_total 1218 _reflns_number_gt 1198 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _computing_structure_solution 'SHELXTL (Sheldrick, 1998)' _computing_structure_refinement 'SHELXTL (Sheldrick, 1998)' _computing_molecular_graphics 'XP (Siemens, 1998)' _computing_publication_material 'SHELXTL (Sheldrick, 1998)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 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^)+(0.0502P)^2^+0.1755P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1218 _refine_ls_number_parameters 84 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0359 _refine_ls_R_factor_gt 0.0353 _refine_ls_wR_factor_ref 0.0905 _refine_ls_wR_factor_gt 0.0895 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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 N1 N 0.20730(12) 0.66624(12) 0.09509(6) 0.01065(17) Uani 1 1 d . . . N3 N -0.04387(12) 0.49000(13) 0.18911(7) 0.01309(18) Uani 1 1 d . . . N4 N 0.10669(12) 0.33304(13) 0.15019(7) 0.01387(18) Uani 1 1 d . . . N6 N 0.33733(12) 0.83242(13) 0.04840(7) 0.01305(18) Uani 1 1 d . . . H6NB H 0.394(2) 0.914(3) 0.1091(14) 0.029(4) Uiso 1 1 d . . . H6NA H 0.249(2) 0.916(3) 0.0000(13) 0.024(3) Uiso 1 1 d . . . N7 N -0.08145(12) 0.88812(13) 0.16403(7) 0.01347(18) Uani 1 1 d . . . H7NB H -0.001(2) 1.008(3) 0.1657(12) 0.018(3) Uiso 1 1 d . . . H7NA H -0.180(2) 0.893(3) 0.2115(13) 0.021(3) Uiso 1 1 d . . . C2 C 0.02066(13) 0.68860(14) 0.15385(7) 0.01090(18) Uani 1 1 d . . . C5 C 0.25268(14) 0.44300(14) 0.09548(7) 0.01239(19) Uani 1 1 d . . . H5 H 0.379(2) 0.379(2) 0.0584(13) 0.021(3) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0099(3) 0.0101(3) 0.0124(3) 0.0007(2) 0.0037(2) -0.0001(2) N3 0.0134(3) 0.0113(3) 0.0151(3) 0.0001(2) 0.0042(2) -0.0006(2) N4 0.0152(3) 0.0108(3) 0.0159(4) 0.0004(2) 0.0037(3) 0.0008(2) N6 0.0124(3) 0.0115(3) 0.0157(4) 0.0027(3) 0.0043(3) -0.0021(2) N7 0.0123(3) 0.0110(3) 0.0178(4) -0.0008(3) 0.0060(3) 0.0003(3) C2 0.0099(3) 0.0126(4) 0.0104(3) -0.0004(3) 0.0024(3) -0.0004(3) C5 0.0128(4) 0.0112(4) 0.0133(4) 0.0002(3) 0.0019(3) 0.0013(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 1.3681(11) . ? N1 C2 1.3735(10) . ? N1 N6 1.4045(10) . ? N3 C2 1.3262(11) . ? N3 N4 1.4130(10) . ? N4 C5 1.3053(11) . ? N6 H6NB 0.897(16) . ? N6 H6NA 0.900(15) . ? N7 C2 1.3607(11) . ? N7 H7NB 0.875(15) . ? N7 H7NA 0.838(15) . ? C5 H5 0.984(14) . ? 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 105.76(7) . . ? C5 N1 N6 125.06(7) . . ? C2 N1 N6 129.10(7) . . ? C2 N3 N4 106.75(7) . . ? C5 N4 N3 107.42(7) . . ? N1 N6 H6NB 107.6(10) . . ? N1 N6 H6NA 106.8(10) . . ? H6NB N6 H6NA 110.7(13) . . ? C2 N7 H7NB 117.4(10) . . ? C2 N7 H7NA 116.3(10) . . ? H7NB N7 H7NA 113.3(14) . . ? N3 C2 N7 127.96(8) . . ? N3 C2 N1 109.64(7) . . ? N7 C2 N1 122.26(8) . . ? N4 C5 N1 110.43(7) . . ? N4 C5 H5 126.5(9) . . ? N1 C5 H5 123.1(9) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 29.99 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.458 _refine_diff_density_min -0.212 _refine_diff_density_rms 0.051 # Attachment 'DATo.CIF' data_experimental_2 _database_code_depnum_ccdc_archive 'CCDC 735986' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C2 H5 N5' _chemical_formula_sum 'C2 H5 N5' _chemical_formula_weight 99.11 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 5.3783(12) _cell_length_b 11.086(3) _cell_length_c 13.580(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 809.7(4) _cell_formula_units_Z 8 _cell_measurement_temperature 164(2) _cell_measurement_reflns_used 12 _cell_measurement_theta_min 2 _cell_measurement_theta_max 25 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.626 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 0.123 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 164(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 'Siemens P3/PC' _diffrn_measurement_method '\q-2\q scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count 98 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 5 _diffrn_reflns_number 1164 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0622 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 30.06 _reflns_number_total 1164 _reflns_number_gt 706 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'P3 (Siemens,1989)' _computing_cell_refinement 'P3 (Siemens,1989)' _computing_data_reduction 'XDISK (Siemens, 1991)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (Siemens, 1998)' _computing_publication_material 'SHELXTL (Sheldrick, 1998)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 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^)+(0.0687P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1164 _refine_ls_number_parameters 84 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1038 _refine_ls_R_factor_gt 0.0416 _refine_ls_wR_factor_ref 0.1096 _refine_ls_wR_factor_gt 0.1010 _refine_ls_goodness_of_fit_ref 0.910 _refine_ls_restrained_S_all 0.910 _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 N1 N 0.0349(2) 0.38718(11) 0.14577(9) 0.0208(3) Uani 1 1 d . . . N4 N 0.0366(3) 0.58266(11) 0.12576(10) 0.0275(3) Uani 1 1 d . . . N3 N 0.2490(2) 0.53480(11) 0.07982(9) 0.0266(3) Uani 1 1 d . . . N7 N 0.4041(3) 0.33596(13) 0.05599(11) 0.0303(3) Uani 1 1 d . . . H7NA H 0.533(4) 0.3683(18) 0.0258(13) 0.031(5) Uiso 1 1 d . . . H7NB H 0.423(4) 0.268(2) 0.0852(14) 0.037(5) Uiso 1 1 d . . . N6 N -0.0411(3) 0.27339(12) 0.18068(11) 0.0282(3) Uani 1 1 d . . . H6NB H 0.084(4) 0.2434(19) 0.2189(15) 0.043(6) Uiso 1 1 d . . . H6NA H -0.066(4) 0.225(2) 0.1295(16) 0.048(6) Uiso 1 1 d . . . C5 C -0.0845(3) 0.49292(14) 0.16340(11) 0.0242(3) Uani 1 1 d . . . H5 H -0.234(3) 0.4988(15) 0.1994(13) 0.026(4) Uiso 1 1 d . . . C2 C 0.2415(3) 0.41700(13) 0.09277(10) 0.0212(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0224(6) 0.0151(5) 0.0249(6) 0.0028(5) 0.0013(5) -0.0017(5) N4 0.0330(7) 0.0179(6) 0.0318(7) -0.0002(5) 0.0029(6) 0.0017(5) N3 0.0302(7) 0.0166(6) 0.0330(6) 0.0023(5) 0.0058(6) -0.0002(5) N7 0.0315(7) 0.0178(6) 0.0415(8) 0.0073(6) 0.0120(6) 0.0049(6) N6 0.0328(8) 0.0166(6) 0.0350(7) 0.0052(6) 0.0044(6) -0.0044(6) C5 0.0262(7) 0.0199(7) 0.0265(7) -0.0007(5) 0.0022(6) 0.0017(6) C2 0.0235(7) 0.0186(6) 0.0214(6) 0.0029(5) 0.0012(6) -0.0022(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 N1 C5 1.358(2) . ? N1 C2 1.3643(19) . ? N1 N6 1.4083(18) . ? N4 C5 1.294(2) . ? N4 N3 1.4056(19) . ? N3 C2 1.3184(19) . ? N7 C2 1.350(2) . ? N7 H7NA 0.883(19) . ? N7 H7NB 0.86(2) . ? N6 H6NB 0.91(2) . ? N6 H6NA 0.89(2) . ? C5 H5 0.943(17) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 N1 C2 105.60(12) . . ? C5 N1 N6 125.22(13) . . ? C2 N1 N6 129.12(12) . . ? C5 N4 N3 107.11(12) . . ? C2 N3 N4 106.84(12) . . ? C2 N7 H7NA 114.3(13) . . ? C2 N7 H7NB 119.4(14) . . ? H7NA N7 H7NB 118.6(19) . . ? N1 N6 H6NB 107.7(14) . . ? N1 N6 H6NA 108.7(14) . . ? H6NB N6 H6NA 110(2) . . ? N4 C5 N1 110.85(14) . . ? N4 C5 H5 125.5(10) . . ? N1 C5 H5 123.7(10) . . ? N3 C2 N7 126.16(14) . . ? N3 C2 N1 109.60(13) . . ? N7 C2 N1 124.17(13) . . ? 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 C5 N4 N3 C2 0.20(16) . . . . ? N3 N4 C5 N1 0.26(17) . . . . ? C2 N1 C5 N4 -0.60(17) . . . . ? N6 N1 C5 N4 176.81(14) . . . . ? N4 N3 C2 N7 176.46(15) . . . . ? N4 N3 C2 N1 -0.57(17) . . . . ? C5 N1 C2 N3 0.72(17) . . . . ? N6 N1 C2 N3 -176.55(14) . . . . ? C5 N1 C2 N7 -176.39(14) . . . . ? N6 N1 C2 N7 6.3(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N7 H7NA N3 0.883(19) 2.14(2) 2.989(2) 161.0(17) 5_665 N7 H7NB N4 0.86(2) 2.14(2) 2.981(2) 167.4(18) 8_655 N6 H6NA N7 0.89(2) 2.61(2) 3.448(2) 156.9(18) 4_455 N6 H6NB N6 0.91(2) 2.46(2) 3.2827(18) 150.6(18) 6_656 _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 30.06 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.240 _refine_diff_density_min -0.254 _refine_diff_density_rms 0.054