# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _audit_creation_method SHELXL-97 _publ_contact_author_name 'Michael Gobel' _publ_contact_author_address ; Chemistry and Biochemistry University of Munich (LMU) Butenandtstr.5-13 (Haus D) Munich 81377 GERMANY ; loop_ _publ_author_name _publ_author_address 'Thomas M. Klapotke' ; Department Chemie Ludwig-Maximilians Universitat Butenandtstrase 5-13 (Haus D) D-81377 Munchen Bundesrepublik Deutschland ; 'Michael Gobel' ; Chemistry and Biochemistry University of Munich (LMU) Butenandtstr.5-13 (Haus D) Munich 81377 GERMANY ; _publ_contact_author_email MIGCH@CUP.UNI-MUENCHEN.DE _publ_section_title ; First Structural Characterization of Guanidine, HN=C(NH2)2 ; data_cx122 _database_code_depnum_ccdc_archive 'CCDC 642807' _chemical_name_systematic '2-amino-4,6-dimethyl-triazine * 1 guanidine' _chemical_name_common '2-amino-4,6-dimethyl-triazine * 1 guanidine' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H13 N7' _chemical_formula_weight 183.23 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 P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.9182(3) _cell_length_b 4.8503(2) _cell_length_c 18.8708(7) _cell_angle_alpha 90.00 _cell_angle_beta 91.382(3) _cell_angle_gamma 90.00 _cell_volume 907.54(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.341 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 0.094 _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 100(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 'Oxford Xcalibur3 CCD' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4341 _diffrn_reflns_av_R_equivalents 0.0193 _diffrn_reflns_av_sigmaI/netI 0.0338 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 4.32 _diffrn_reflns_theta_max 25.99 _reflns_number_total 1755 _reflns_number_gt 1257 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0501P)^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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1755 _refine_ls_number_parameters 170 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0499 _refine_ls_R_factor_gt 0.0327 _refine_ls_wR_factor_ref 0.0837 _refine_ls_wR_factor_gt 0.0770 _refine_ls_goodness_of_fit_ref 0.969 _refine_ls_restrained_S_all 0.969 _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 C1 C 0.87358(12) 0.6204(3) 0.16879(6) 0.0186(3) Uani 1 1 d . . . C2 C 0.37024(12) 0.6244(3) 0.14317(6) 0.0198(3) Uani 1 1 d . . . C3 C 0.26715(12) 0.3355(3) 0.06441(6) 0.0197(3) Uani 1 1 d . . . C4 C 0.49477(12) 0.3280(3) 0.07882(6) 0.0181(3) Uani 1 1 d . . . C5 C 0.36133(15) 0.8422(3) 0.19809(8) 0.0232(3) Uani 1 1 d . . . C6 C 0.14236(14) 0.2242(4) 0.02880(8) 0.0262(4) Uani 1 1 d . . . N1 N 0.85800(11) 0.3754(2) 0.14260(6) 0.0215(3) Uani 1 1 d . . . N2 N 0.99553(12) 0.7289(3) 0.18926(7) 0.0272(3) Uani 1 1 d . . . N3 N 0.76486(12) 0.7810(3) 0.18121(6) 0.0221(3) Uani 1 1 d . . . N4 N 0.38280(10) 0.2249(2) 0.04552(5) 0.0189(3) Uani 1 1 d . . . N5 N 0.49181(10) 0.5323(2) 0.12786(5) 0.0195(3) Uani 1 1 d . . . N6 N 0.25286(10) 0.5333(2) 0.11368(5) 0.0208(3) Uani 1 1 d . . . N7 N 0.61268(11) 0.2210(3) 0.06285(6) 0.0215(3) Uani 1 1 d . . . H1 H 0.9383(16) 0.292(3) 0.1405(7) 0.030(4) Uiso 1 1 d . . . H2A H 1.0724(18) 0.662(3) 0.1682(9) 0.047(5) Uiso 1 1 d . . . H2B H 0.9964(15) 0.889(3) 0.2095(8) 0.031(4) Uiso 1 1 d . . . H3A H 0.7775(15) 0.951(3) 0.1801(7) 0.026(4) Uiso 1 1 d . . . H3B H 0.6844(15) 0.711(3) 0.1659(8) 0.027(4) Uiso 1 1 d . . . H5A H 0.3346(17) 0.758(3) 0.2403(10) 0.050(5) Uiso 1 1 d . . . H5B H 0.2947(16) 0.972(3) 0.1854(8) 0.040(4) Uiso 1 1 d . . . H5C H 0.4480(18) 0.925(3) 0.2062(8) 0.042(4) Uiso 1 1 d . . . H6A H 0.1516(17) 0.205(4) -0.0200(10) 0.052(5) Uiso 1 1 d . . . H6B H 0.1267(17) 0.050(4) 0.0467(10) 0.051(5) Uiso 1 1 d . . . H6C H 0.0601(16) 0.334(3) 0.0389(8) 0.034(4) Uiso 1 1 d . . . H7A H 0.6151(13) 0.090(3) 0.0326(8) 0.019(4) Uiso 1 1 d . . . H7B H 0.6889(15) 0.284(3) 0.0858(8) 0.028(4) 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 C1 0.0183(6) 0.0208(7) 0.0165(6) 0.0036(6) 0.0005(5) -0.0005(6) C2 0.0213(7) 0.0178(7) 0.0203(6) 0.0055(6) 0.0010(5) 0.0001(6) C3 0.0195(6) 0.0213(8) 0.0182(7) 0.0039(6) -0.0009(5) 0.0007(6) C4 0.0187(7) 0.0184(7) 0.0172(6) 0.0026(6) -0.0004(5) -0.0006(5) C5 0.0231(7) 0.0221(8) 0.0244(7) -0.0019(6) 0.0022(6) 0.0005(7) C6 0.0195(7) 0.0332(10) 0.0257(8) -0.0038(7) -0.0027(6) 0.0014(7) N1 0.0174(6) 0.0185(6) 0.0286(6) -0.0022(5) -0.0008(4) 0.0023(5) N2 0.0176(6) 0.0254(8) 0.0386(7) -0.0104(6) -0.0007(5) -0.0012(6) N3 0.0177(6) 0.0162(7) 0.0325(7) -0.0018(6) 0.0011(5) -0.0003(5) N4 0.0176(5) 0.0204(6) 0.0187(6) 0.0006(5) -0.0014(4) 0.0010(5) N5 0.0203(6) 0.0175(6) 0.0208(6) -0.0010(5) 0.0000(4) 0.0009(5) N6 0.0194(6) 0.0213(6) 0.0218(6) 0.0009(5) -0.0004(4) 0.0005(5) N7 0.0179(6) 0.0218(7) 0.0246(6) -0.0074(6) -0.0025(5) 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 C1 N1 1.2951(17) . ? C1 N3 1.3552(17) . ? C1 N2 1.3660(17) . ? C2 N5 1.3242(16) . ? C2 N6 1.3525(16) . ? C2 C5 1.4837(19) . ? C3 N4 1.3229(16) . ? C3 N6 1.3461(16) . ? C3 C6 1.4947(18) . ? C4 N7 1.3207(16) . ? C4 N5 1.3567(16) . ? C4 N4 1.3582(16) . ? C5 H5A 0.939(18) . ? C5 H5B 0.941(16) . ? C5 H5C 0.957(17) . ? C6 H6A 0.932(19) . ? C6 H6B 0.926(19) . ? C6 H6C 0.995(16) . ? N1 H1 0.895(16) . ? N2 H2A 0.927(18) . ? N2 H2B 0.864(16) . ? N3 H3A 0.834(16) . ? N3 H3B 0.908(15) . ? N7 H7A 0.856(15) . ? N7 H7B 0.915(15) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 N3 120.36(12) . . ? N1 C1 N2 123.91(12) . . ? N3 C1 N2 115.63(13) . . ? N5 C2 N6 125.39(12) . . ? N5 C2 C5 117.55(12) . . ? N6 C2 C5 117.05(11) . . ? N4 C3 N6 125.56(11) . . ? N4 C3 C6 116.52(12) . . ? N6 C3 C6 117.90(12) . . ? N7 C4 N5 118.45(11) . . ? N7 C4 N4 117.93(12) . . ? N5 C4 N4 123.61(11) . . ? C2 C5 H5A 107.9(10) . . ? C2 C5 H5B 110.7(9) . . ? H5A C5 H5B 107.2(13) . . ? C2 C5 H5C 110.0(9) . . ? H5A C5 H5C 108.5(14) . . ? H5B C5 H5C 112.4(13) . . ? C3 C6 H6A 112.4(10) . . ? C3 C6 H6B 108.1(11) . . ? H6A C6 H6B 106.9(16) . . ? C3 C6 H6C 113.2(8) . . ? H6A C6 H6C 110.1(14) . . ? H6B C6 H6C 105.7(14) . . ? C1 N1 H1 109.5(9) . . ? C1 N2 H2A 118.4(10) . . ? C1 N2 H2B 118.0(10) . . ? H2A N2 H2B 120.2(15) . . ? C1 N3 H3A 116.3(10) . . ? C1 N3 H3B 115.2(9) . . ? H3A N3 H3B 119.5(14) . . ? C3 N4 C4 115.51(11) . . ? C2 N5 C4 115.48(11) . . ? C3 N6 C2 114.41(11) . . ? C4 N7 H7A 118.9(9) . . ? C4 N7 H7B 119.1(9) . . ? H7A N7 H7B 121.9(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 N6 C3 N4 C4 -1.22(19) . . . . ? C6 C3 N4 C4 -179.63(12) . . . . ? N7 C4 N4 C3 178.75(11) . . . . ? N5 C4 N4 C3 -0.65(18) . . . . ? N6 C2 N5 C4 -0.66(19) . . . . ? C5 C2 N5 C4 178.20(12) . . . . ? N7 C4 N5 C2 -177.88(11) . . . . ? N4 C4 N5 C2 1.52(18) . . . . ? N4 C3 N6 C2 1.96(18) . . . . ? C6 C3 N6 C2 -179.64(12) . . . . ? N5 C2 N6 C3 -0.95(18) . . . . ? C5 C2 N6 C3 -179.82(12) . . . . ? 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 N3 H3B N5 0.908(15) 2.202(16) 3.1100(16) 178.7(13) . N2 H2A N6 0.927(18) 2.177(19) 3.1021(17) 175.7(15) 1_655 N7 H7A N4 0.856(15) 2.122(16) 2.9777(17) 177.6(12) 3_655 N7 H7B N1 0.915(15) 2.018(16) 2.9273(16) 172.5(13) . _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.145 _refine_diff_density_min -0.196 _refine_diff_density_rms 0.039 data_cx001 _database_code_depnum_ccdc_archive 'CCDC 642808' _chemical_name_systematic '2-amino-4,6-dimethyl-triazine * 2 guanidine' _chemical_name_common '2-amino-4,6-dimethyl-triazine * 2 guanidine' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H18 N10' _chemical_formula_weight 242.31 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 P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.5743(2) _cell_length_b 23.7968(7) _cell_length_c 7.8931(2) _cell_angle_alpha 90.00 _cell_angle_beta 96.373(2) _cell_angle_gamma 90.00 _cell_volume 1227.22(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.311 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.094 _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 100(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 'Oxford Xcalibur3 CCD' _diffrn_measurement_method omega-scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12408 _diffrn_reflns_av_R_equivalents 0.0385 _diffrn_reflns_av_sigmaI/netI 0.0356 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.93 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2148 _reflns_number_gt 1507 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0632P)^2^+0.2092P] 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 2148 _refine_ls_number_parameters 204 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0690 _refine_ls_R_factor_gt 0.0412 _refine_ls_wR_factor_ref 0.1136 _refine_ls_wR_factor_gt 0.0986 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _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 C1 C 1.1131(3) 0.17405(8) -0.3559(2) 0.0227(5) Uani 1 1 d . . . C2 C 0.9226(3) 0.02369(8) 0.1990(2) 0.0216(5) Uani 1 1 d . . . C3 C 1.2022(3) 0.07742(8) 0.2723(2) 0.0218(5) Uani 1 1 d . . . C4 C 1.1945(3) -0.01296(8) 0.3636(2) 0.0193(4) Uani 1 1 d . . . C5 C 0.7128(3) 0.01670(9) 0.1091(2) 0.0277(5) Uani 1 1 d . . . H5A H 0.7089 -0.0166 0.0359 0.042 Uiso 1 1 calc R . . H5B H 0.6765 0.0500 0.0391 0.042 Uiso 1 1 calc R . . H5C H 0.6149 0.0121 0.1931 0.042 Uiso 1 1 calc R . . C6 C 1.3102(3) 0.13233(9) 0.2634(3) 0.0304(5) Uani 1 1 d . . . H6A H 1.2497 0.1599 0.3352 0.046 Uiso 1 1 calc R . . H6B H 1.2964 0.1457 0.1452 0.046 Uiso 1 1 calc R . . H6C H 1.4555 0.1275 0.3040 0.046 Uiso 1 1 calc R . . C7 C 0.6987(3) 0.19314(8) -0.0023(2) 0.0207(4) Uani 1 1 d . . . N1 N 0.9327(3) 0.16365(8) -0.4357(2) 0.0251(4) Uani 1 1 d . . . N2 N 1.2296(3) 0.13142(9) -0.2866(3) 0.0349(5) Uani 1 1 d . . . N3 N 1.2010(3) 0.22571(8) -0.3380(2) 0.0332(5) Uani 1 1 d . . . N4 N 1.0035(2) -0.02060(7) 0.28301(19) 0.0210(4) Uani 1 1 d . . . N5 N 1.0129(2) 0.07409(7) 0.1878(2) 0.0235(4) Uani 1 1 d . . . N6 N 1.2998(2) 0.03625(7) 0.36115(19) 0.0212(4) Uani 1 1 d . . . N7 N 1.2841(3) -0.05568(8) 0.4489(2) 0.0229(4) Uani 1 1 d . . . N8 N 0.5810(3) 0.23103(8) -0.0809(2) 0.0268(4) Uani 1 1 d . . . N9 N 0.7658(3) 0.19371(8) 0.1669(2) 0.0274(4) Uani 1 1 d . . . N10 N 0.7651(3) 0.14895(8) -0.0907(2) 0.0307(5) Uani 1 1 d . . . H1 H 0.882(3) 0.1937(9) -0.471(2) 0.017(5) Uiso 1 1 d . . . H2A H 1.174(4) 0.0971(11) -0.293(3) 0.048(7) Uiso 1 1 d . . . H2B H 1.349(4) 0.1382(10) -0.230(3) 0.048(8) Uiso 1 1 d . . . H3A H 1.307(4) 0.2310(10) -0.262(3) 0.042(7) Uiso 1 1 d . . . H3B H 1.114(4) 0.2529(11) -0.353(3) 0.040(7) Uiso 1 1 d . . . H7A H 1.217(3) -0.0879(10) 0.447(3) 0.032(6) Uiso 1 1 d . . . H7B H 1.413(4) -0.0512(9) 0.508(3) 0.034(6) Uiso 1 1 d . . . H8 H 0.540(3) 0.2551(9) -0.007(3) 0.029(6) Uiso 1 1 d . . . H9A H 0.696(3) 0.2176(10) 0.234(3) 0.032(6) Uiso 1 1 d . . . H9B H 0.819(4) 0.1644(12) 0.213(3) 0.056(8) Uiso 1 1 d . . . H10A H 0.861(4) 0.1278(10) -0.040(3) 0.039(7) Uiso 1 1 d . . . H10B H 0.774(4) 0.1548(10) -0.203(3) 0.045(7) 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 C1 0.0254(11) 0.0239(11) 0.0191(9) -0.0023(8) 0.0036(8) -0.0051(9) C2 0.0193(10) 0.0247(11) 0.0211(10) -0.0024(8) 0.0033(8) 0.0014(9) C3 0.0194(11) 0.0234(11) 0.0234(10) -0.0017(8) 0.0055(8) 0.0009(8) C4 0.0168(10) 0.0230(11) 0.0180(9) -0.0028(8) 0.0018(8) 0.0009(8) C5 0.0216(11) 0.0302(12) 0.0298(11) 0.0022(9) -0.0034(9) 0.0009(9) C6 0.0251(12) 0.0249(12) 0.0411(12) 0.0063(10) 0.0023(10) -0.0016(9) C7 0.0168(10) 0.0229(11) 0.0224(10) 0.0005(9) 0.0027(8) -0.0046(9) N1 0.0263(10) 0.0221(10) 0.0260(9) 0.0019(8) -0.0015(7) 0.0002(8) N2 0.0262(11) 0.0251(11) 0.0501(12) 0.0009(9) -0.0107(9) -0.0022(9) N3 0.0334(12) 0.0266(11) 0.0367(11) 0.0014(9) -0.0083(9) -0.0069(10) N4 0.0166(9) 0.0227(9) 0.0232(8) -0.0003(7) 0.0005(7) -0.0003(7) N5 0.0204(9) 0.0236(10) 0.0264(9) 0.0023(7) 0.0029(7) 0.0012(7) N6 0.0191(9) 0.0201(9) 0.0242(8) -0.0018(7) 0.0017(7) -0.0006(7) N7 0.0201(9) 0.0197(10) 0.0273(9) 0.0000(7) -0.0039(7) -0.0015(8) N8 0.0266(10) 0.0275(10) 0.0258(9) -0.0007(8) 0.0010(8) 0.0019(8) N9 0.0331(11) 0.0262(11) 0.0220(9) 0.0003(8) -0.0009(8) 0.0032(9) N10 0.0379(12) 0.0287(11) 0.0256(10) 0.0033(8) 0.0042(9) 0.0082(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.304(2) . ? C1 N2 1.350(3) . ? C1 N3 1.359(3) . ? C2 N4 1.325(2) . ? C2 N5 1.345(2) . ? C2 C5 1.489(3) . ? C3 N6 1.328(2) . ? C3 N5 1.347(2) . ? C3 C6 1.493(3) . ? C4 N7 1.321(2) . ? C4 N4 1.356(2) . ? C4 N6 1.362(2) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 N8 1.300(2) . ? C7 N9 1.359(2) . ? C7 N10 1.361(3) . ? N1 H1 0.82(2) . ? N2 H2A 0.89(3) . ? N2 H2B 0.87(3) . ? N3 H3A 0.88(3) . ? N3 H3B 0.86(3) . ? N7 H7A 0.88(2) . ? N7 H7B 0.93(2) . ? N8 H8 0.88(2) . ? N9 H9A 0.93(2) . ? N9 H9B 0.84(3) . ? N10 H10A 0.87(2) . ? N10 H10B 0.91(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 N2 119.87(19) . . ? N1 C1 N3 125.16(19) . . ? N2 C1 N3 114.96(19) . . ? N4 C2 N5 125.92(17) . . ? N4 C2 C5 116.66(17) . . ? N5 C2 C5 117.42(17) . . ? N6 C3 N5 125.72(18) . . ? N6 C3 C6 117.76(17) . . ? N5 C3 C6 116.52(17) . . ? N7 C4 N4 118.24(17) . . ? N7 C4 N6 118.07(17) . . ? N4 C4 N6 123.68(16) . . ? C2 C5 H5A 109.5 . . ? C2 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C2 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C3 C6 H6A 109.5 . . ? C3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N8 C7 N9 125.00(19) . . ? N8 C7 N10 119.93(18) . . ? N9 C7 N10 115.07(19) . . ? C1 N1 H1 108.3(13) . . ? C1 N2 H2A 116.8(15) . . ? C1 N2 H2B 120.3(16) . . ? H2A N2 H2B 123(2) . . ? C1 N3 H3A 119.7(15) . . ? C1 N3 H3B 113.3(16) . . ? H3A N3 H3B 117(2) . . ? C2 N4 C4 115.31(16) . . ? C2 N5 C3 114.20(16) . . ? C3 N6 C4 115.17(16) . . ? C4 N7 H7A 117.7(14) . . ? C4 N7 H7B 120.0(13) . . ? H7A N7 H7B 122(2) . . ? C7 N8 H8 110.2(14) . . ? C7 N9 H9A 116.1(13) . . ? C7 N9 H9B 119.1(18) . . ? H9A N9 H9B 118(2) . . ? C7 N10 H10A 117.8(15) . . ? C7 N10 H10B 116.2(16) . . ? H10A N10 H10B 115(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 N5 C2 N4 C4 0.0(3) . . . . ? C5 C2 N4 C4 -179.97(16) . . . . ? N7 C4 N4 C2 -179.61(17) . . . . ? N6 C4 N4 C2 0.1(3) . . . . ? N4 C2 N5 C3 -0.1(3) . . . . ? C5 C2 N5 C3 179.93(16) . . . . ? N6 C3 N5 C2 0.0(3) . . . . ? C6 C3 N5 C2 179.65(17) . . . . ? N5 C3 N6 C4 0.2(3) . . . . ? C6 C3 N6 C4 -179.49(17) . . . . ? N7 C4 N6 C3 179.50(17) . . . . ? N4 C4 N6 C3 -0.2(3) . . . . ? 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 N2 H2A N4 0.89(3) 2.17(3) 3.052(3) 170(2) 3_755 N3 H3A N8 0.88(3) 2.17(3) 3.041(3) 171(2) 1_655 N9 H9A N8 0.93(2) 2.11(3) 3.030(3) 170.2(18) 4_566 N7 H7A N1 0.88(2) 2.05(2) 2.934(3) 178(2) 3_755 N7 H7B N6 0.93(2) 2.08(2) 3.006(2) 176.7(19) 3_856 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.201 _refine_diff_density_min -0.247 _refine_diff_density_rms 0.046