# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2001 data_global #=========================================================================== #SUBMISSION DETAILS _journal_coden_Cambridge 182 _publ_contact_author 'Prof Roger Guilard' _publ_contact_author_address ; Prof Roger Guilard, LIMSAG, CNRS UMR 5633, Universite de Bourgogne, Faculte des Sciences, 6 boulevard Gabriel, 21100 Dijon, France ; _publ_contact_author_phone '+33 3 80 39 61 11' _publ_contact_author_fax '+33 3 80 39 61 17' _publ_contact_author_email Roger.Guilard@u-bourgogne.fr _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'Boschetti, Frederic' 'Denat, Franck' 'Espinosa, Enrique' 'Guilard, Roger' #=========================================================================== # TITLE _publ_section_title ; An organic template approach for the synthesis of selectively functionalised tetraazacycloalkanes. ; #=========================================================================== data_fbo200 _database_code_CSD 172981 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H31 N4,Br,3(C H Cl3)' _chemical_formula_sum 'C23 H34 Br Cl9 N4' _chemical_formula_weight 765.50 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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Br' 'Br' -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'Monoclinic' _symmetry_space_group_name_H-M 'P 21/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 10.4280(2) _cell_length_b 28.2670(7) _cell_length_c 11.6960(4) _cell_angle_alpha 90.00 _cell_angle_beta 110.5440(10) _cell_angle_gamma 90.00 _cell_volume 3228.35(15) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 12777 _cell_measurement_theta_min 1.99 _cell_measurement_theta_max 27.45 _exptl_crystal_description 'Plate' _exptl_crystal_colour 'Colourless' _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.575 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1552 _exptl_absorpt_coefficient_mu 2.040 _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 110(2) _diffrn_radiation_wavelength 0.71070 _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 12777 _diffrn_reflns_av_R_equivalents 0.0999 _diffrn_reflns_av_sigmaI/netI 0.1975 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -36 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 27.45 _reflns_number_total 7271 _reflns_number_gt 3307 _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^)+(0.0214P)^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 0.00035(14) _refine_ls_extinction_expression 'Fc^*^==kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 7271 _refine_ls_number_parameters 346 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1746 _refine_ls_R_factor_gt 0.0549 _refine_ls_wR_factor_ref 0.0958 _refine_ls_wR_factor_gt 0.0743 _refine_ls_goodness_of_fit_ref 0.922 _refine_ls_restrained_S_all 0.922 _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 Br1 Br 0.13896(5) -0.183244(16) 0.93581(4) 0.02853(15) Uani 1 1 d . . . N1 N 0.1465(3) 0.17991(12) 0.4746(3) 0.0177(8) Uani 1 1 d . . . N2 N 0.1130(3) 0.09155(11) 0.3308(3) 0.0192(9) Uani 1 1 d . . . N3 N 0.2971(3) 0.11603(12) 0.2615(3) 0.0223(9) Uani 1 1 d . . . N4 N 0.3596(3) 0.13516(12) 0.5155(3) 0.0218(9) Uani 1 1 d . . . C1 C 0.0653(4) 0.13703(14) 0.4885(4) 0.0180(11) Uani 1 1 d . . . H1A H 0.1250 0.1164 0.5508 0.0185(19) Uiso 1 1 calc R . . H1B H -0.0079 0.1474 0.5158 0.0185(19) Uiso 1 1 calc R . . C2 C 0.0048(4) 0.10967(14) 0.3720(4) 0.0227(11) Uani 1 1 d . . . H2A H -0.0486 0.0834 0.3849 0.0185(19) Uiso 1 1 calc R . . H2B H -0.0561 0.1300 0.3095 0.0185(19) Uiso 1 1 calc R . . C3 C 0.0474(4) 0.06485(14) 0.2160(4) 0.0242(12) Uani 1 1 d . . . H3A H -0.0206 0.0848 0.1582 0.0185(19) Uiso 1 1 calc R . . H3B H 0.0005 0.0375 0.2328 0.0185(19) Uiso 1 1 calc R . . C4 C 0.1503(4) 0.04834(15) 0.1588(4) 0.0310(13) Uani 1 1 d . . . H4A H 0.2092 0.0242 0.2096 0.0185(19) Uiso 1 1 calc R . . H4B H 0.1023 0.0348 0.0790 0.0185(19) Uiso 1 1 calc R . . C5 C 0.2357(4) 0.09019(15) 0.1468(4) 0.0276(12) Uani 1 1 d . . . H5A H 0.3079 0.0790 0.1192 0.0185(19) Uiso 1 1 calc R . . H5B H 0.1783 0.1116 0.0852 0.0185(19) Uiso 1 1 calc R . . C6 C 0.3989(4) 0.08744(15) 0.3544(4) 0.0271(12) Uani 1 1 d . . . H6A H 0.4693 0.0772 0.3234 0.0185(19) Uiso 1 1 calc R . . H6B H 0.3552 0.0595 0.3722 0.0185(19) Uiso 1 1 calc R . . C7 C 0.4628(4) 0.11557(15) 0.4688(4) 0.0268(12) Uani 1 1 d . . . H7A H 0.5253 0.0955 0.5308 0.0185(19) Uiso 1 1 calc R . . H7B H 0.5155 0.1413 0.4526 0.0185(19) Uiso 1 1 calc R . . C8 C 0.4289(4) 0.16036(15) 0.6307(4) 0.0274(12) Uani 1 1 d . . . H8A H 0.4711 0.1890 0.6150 0.0185(19) Uiso 1 1 calc R . . H8B H 0.5000 0.1406 0.6855 0.0185(19) Uiso 1 1 calc R . . C9 C 0.3240(4) 0.17245(15) 0.6881(4) 0.0235(11) Uani 1 1 d . . . H9A H 0.2859 0.1436 0.7078 0.0185(19) Uiso 1 1 calc R . . H9B H 0.3674 0.1899 0.7632 0.0185(19) Uiso 1 1 calc R . . C10 C 0.2113(4) 0.20189(14) 0.6009(4) 0.0212(11) Uani 1 1 d . . . H10A H 0.2481 0.2327 0.5923 0.0185(19) Uiso 1 1 calc R . . H10B H 0.1406 0.2068 0.6358 0.0185(19) Uiso 1 1 calc R . . C11 C 0.0523(4) 0.21755(13) 0.3917(4) 0.0200(11) Uani 1 1 d . . . H11A H 0.1074 0.2450 0.3899 0.0185(19) Uiso 1 1 calc R . . H11B H 0.0156 0.2050 0.3094 0.0185(19) Uiso 1 1 calc R . . C12 C -0.0662(4) 0.23366(15) 0.4283(4) 0.0193(11) Uani 1 1 d . . . C13 C -0.0508(5) 0.27027(14) 0.5113(4) 0.0242(12) Uani 1 1 d . . . H13 H 0.0352 0.2835 0.5501 0.0185(19) Uiso 1 1 calc R . . C14 C -0.1629(5) 0.28737(16) 0.5368(4) 0.0319(13) Uani 1 1 d . . . H14 H -0.1514 0.3117 0.5932 0.0185(19) Uiso 1 1 calc R . . C15 C -0.2902(5) 0.26841(17) 0.4790(5) 0.0386(15) Uani 1 1 d . . . H15 H -0.3646 0.2793 0.4979 0.0185(19) Uiso 1 1 calc R . . C16 C -0.3088(5) 0.23327(16) 0.3929(5) 0.0333(14) Uani 1 1 d . . . H16 H -0.3959 0.2213 0.3519 0.0185(19) Uiso 1 1 calc R . . C17 C -0.1963(4) 0.21574(15) 0.3676(4) 0.0265(12) Uani 1 1 d . . . H17 H -0.2087 0.1920 0.3097 0.0185(19) Uiso 1 1 calc R . . C21 C 0.1890(4) 0.13193(14) 0.3049(4) 0.0201(11) Uani 1 1 d . . . H21 H 0.1245 0.1515 0.2412 0.0185(19) Uiso 1 1 calc R . . C41 C 0.2579(4) 0.16359(14) 0.4195(4) 0.0171(11) Uani 1 1 d . . . C42 C 0.3182(4) 0.20763(13) 0.3790(4) 0.0245(12) Uani 1 1 d . . . H42A H 0.3435 0.2306 0.4435 0.0185(19) Uiso 1 1 calc R . . H42B H 0.2510 0.2210 0.3075 0.0185(19) Uiso 1 1 calc R . . H42C H 0.3977 0.1987 0.3607 0.0185(19) Uiso 1 1 calc R . . C50 C 0.2706(5) 0.02111(16) 0.5683(5) 0.0305(13) Uani 1 1 d . . . H50 H 0.254(4) 0.0453(12) 0.515(3) 0.0185(19) Uiso 1 1 d . . . Cl1 Cl 0.15132(13) 0.02402(4) 0.64386(12) 0.0401(4) Uani 1 1 d . . . Cl2 Cl 0.43863(13) 0.02362(4) 0.67428(13) 0.0420(4) Uani 1 1 d . . . Cl3 Cl 0.24468(13) -0.03024(4) 0.47842(12) 0.0396(4) Uani 1 1 d . . . C60 C 0.3604(5) -0.08469(17) 0.9581(4) 0.0297(13) Uani 1 1 d . . . H60 H 0.294(4) -0.0991(13) 0.965(4) 0.0185(19) Uiso 1 1 d . . . Cl4 Cl 0.32094(13) -0.02585(4) 0.98018(14) 0.0499(4) Uani 1 1 d . . . Cl5 Cl 0.52120(13) -0.10046(5) 1.06277(12) 0.0468(4) Uani 1 1 d . . . Cl6 Cl 0.35632(13) -0.09289(5) 0.80820(12) 0.0506(4) Uani 1 1 d . . . C70 C 0.0987(5) -0.13557(16) 1.1935(4) 0.0294(13) Uani 1 1 d . . . H70 H 0.084(3) -0.1538(12) 1.116(3) 0.0185(19) Uiso 1 1 d . . . Cl7 Cl -0.05949(13) -0.11339(5) 1.19154(13) 0.0530(4) Uani 1 1 d . . . Cl8 Cl 0.21406(14) -0.08887(4) 1.20408(13) 0.0505(4) Uani 1 1 d . . . Cl9 Cl 0.16731(15) -0.17472(5) 1.31639(14) 0.0597(5) 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 Br1 0.0395(3) 0.0234(3) 0.0256(3) 0.0012(3) 0.0150(2) 0.0035(3) N1 0.0185(19) 0.016(2) 0.019(2) 0.0004(19) 0.0074(18) 0.0019(17) N2 0.025(2) 0.016(2) 0.020(2) -0.0060(18) 0.013(2) -0.0023(17) N3 0.024(2) 0.024(2) 0.022(3) -0.0004(19) 0.011(2) 0.0032(18) N4 0.021(2) 0.023(2) 0.023(3) 0.002(2) 0.010(2) 0.0076(18) C1 0.016(2) 0.019(3) 0.023(3) 0.004(2) 0.011(2) 0.001(2) C2 0.027(3) 0.015(3) 0.029(3) 0.000(2) 0.014(3) -0.002(2) C3 0.031(3) 0.015(3) 0.027(3) -0.002(2) 0.011(3) -0.006(2) C4 0.040(3) 0.028(3) 0.025(3) -0.009(2) 0.011(3) -0.001(2) C5 0.033(3) 0.028(3) 0.025(3) -0.003(3) 0.015(3) 0.004(2) C6 0.029(3) 0.026(3) 0.033(3) -0.002(3) 0.020(3) 0.005(2) C7 0.022(3) 0.030(3) 0.031(3) 0.011(3) 0.012(3) 0.010(2) C8 0.026(3) 0.029(3) 0.026(3) 0.001(2) 0.006(3) -0.001(2) C9 0.020(3) 0.030(3) 0.017(3) -0.006(2) 0.002(2) -0.003(2) C10 0.025(3) 0.022(3) 0.018(3) -0.010(2) 0.009(2) -0.005(2) C11 0.024(3) 0.017(3) 0.019(3) 0.009(2) 0.007(2) 0.003(2) C12 0.019(3) 0.018(3) 0.023(3) 0.008(2) 0.010(2) 0.003(2) C13 0.027(3) 0.021(3) 0.027(3) 0.003(2) 0.013(3) 0.004(2) C14 0.049(4) 0.027(3) 0.027(4) 0.007(2) 0.021(3) 0.015(3) C15 0.041(4) 0.036(4) 0.052(4) 0.016(3) 0.032(3) 0.019(3) C16 0.026(3) 0.028(3) 0.054(4) 0.011(3) 0.025(3) 0.004(2) C17 0.032(3) 0.023(3) 0.029(3) 0.006(2) 0.016(3) 0.003(2) C21 0.019(3) 0.023(3) 0.021(3) 0.002(2) 0.010(2) 0.001(2) C41 0.015(2) 0.018(3) 0.024(3) -0.003(2) 0.013(2) 0.000(2) C42 0.023(3) 0.024(3) 0.030(3) 0.000(2) 0.014(3) -0.004(2) C50 0.039(3) 0.019(3) 0.039(4) 0.003(3) 0.019(3) 0.004(2) Cl1 0.0559(9) 0.0304(8) 0.0496(10) 0.0101(7) 0.0379(8) 0.0116(6) Cl2 0.0421(8) 0.0312(8) 0.0461(10) 0.0016(7) 0.0071(7) 0.0011(6) Cl3 0.0445(8) 0.0359(8) 0.0393(9) -0.0102(7) 0.0158(7) 0.0043(6) C60 0.026(3) 0.040(3) 0.025(3) -0.001(3) 0.011(3) -0.007(2) Cl4 0.0446(9) 0.0339(8) 0.0705(12) 0.0095(8) 0.0194(8) 0.0026(7) Cl5 0.0487(9) 0.0507(9) 0.0336(9) 0.0053(8) 0.0051(7) 0.0148(7) Cl6 0.0407(8) 0.0860(12) 0.0275(9) -0.0008(8) 0.0152(7) -0.0195(7) C70 0.034(3) 0.032(3) 0.026(3) -0.005(3) 0.016(3) -0.003(2) Cl7 0.0442(9) 0.0831(11) 0.0363(10) 0.0031(8) 0.0199(8) 0.0179(8) Cl8 0.0645(10) 0.0413(9) 0.0522(11) -0.0124(8) 0.0283(9) -0.0175(7) Cl9 0.0712(10) 0.0634(11) 0.0589(11) 0.0288(9) 0.0407(9) 0.0251(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.519(4) . ? N1 C10 1.525(5) . ? N1 C11 1.539(5) . ? N1 C41 1.582(4) . ? N2 C2 1.466(4) . ? N2 C21 1.480(4) . ? N2 C3 1.482(5) . ? N3 C21 1.460(4) . ? N3 C5 1.463(5) . ? N3 C6 1.467(5) . ? N4 C8 1.470(5) . ? N4 C7 1.475(4) . ? N4 C41 1.482(5) . ? C1 C2 1.500(5) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.523(5) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.517(5) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.497(5) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.510(5) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.508(5) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.512(5) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C17 1.388(6) . ? C12 C13 1.389(5) . ? C13 C14 1.390(5) . ? C13 H13 0.9300 . ? C14 C15 1.370(6) . ? C14 H14 0.9300 . ? C15 C16 1.378(6) . ? C15 H15 0.9300 . ? C16 C17 1.398(5) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C21 C41 1.561(5) . ? C21 H21 0.9800 . ? C41 C42 1.543(5) . ? C42 H42A 0.9600 . ? C42 H42B 0.9600 . ? C42 H42C 0.9600 . ? C50 Cl3 1.757(5) . ? C50 Cl2 1.757(5) . ? C50 Cl1 1.763(4) . ? C50 H50 0.90(3) . ? C60 Cl5 1.752(5) . ? C60 Cl4 1.754(5) . ? C60 Cl6 1.754(5) . ? C60 H60 0.83(3) . ? C70 Cl9 1.755(5) . ? C70 Cl7 1.757(4) . ? C70 Cl8 1.761(4) . ? C70 H70 1.01(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 C1 N1 C10 107.2(3) . . ? C1 N1 C11 111.2(3) . . ? C10 N1 C11 107.2(3) . . ? C1 N1 C41 109.1(3) . . ? C10 N1 C41 112.0(3) . . ? C11 N1 C41 110.1(3) . . ? C2 N2 C21 109.1(3) . . ? C2 N2 C3 108.2(3) . . ? C21 N2 C3 108.5(3) . . ? C21 N3 C5 109.3(3) . . ? C21 N3 C6 111.0(3) . . ? C5 N3 C6 112.0(3) . . ? C8 N4 C7 109.5(3) . . ? C8 N4 C41 115.0(3) . . ? C7 N4 C41 110.1(3) . . ? C2 C1 N1 112.8(3) . . ? C2 C1 H1A 109.0 . . ? N1 C1 H1A 109.0 . . ? C2 C1 H1B 109.0 . . ? N1 C1 H1B 109.0 . . ? H1A C1 H1B 107.8 . . ? N2 C2 C1 110.6(3) . . ? N2 C2 H2A 109.5 . . ? C1 C2 H2A 109.5 . . ? N2 C2 H2B 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 108.1 . . ? N2 C3 C4 112.4(3) . . ? N2 C3 H3A 109.1 . . ? C4 C3 H3A 109.1 . . ? N2 C3 H3B 109.1 . . ? C4 C3 H3B 109.1 . . ? H3A C3 H3B 107.8 . . ? C5 C4 C3 109.2(3) . . ? C5 C4 H4A 109.8 . . ? C3 C4 H4A 109.8 . . ? C5 C4 H4B 109.8 . . ? C3 C4 H4B 109.8 . . ? H4A C4 H4B 108.3 . . ? N3 C5 C4 112.7(3) . . ? N3 C5 H5A 109.0 . . ? C4 C5 H5A 109.0 . . ? N3 C5 H5B 109.0 . . ? C4 C5 H5B 109.0 . . ? H5A C5 H5B 107.8 . . ? N3 C6 C7 110.4(4) . . ? N3 C6 H6A 109.6 . . ? C7 C6 H6A 109.6 . . ? N3 C6 H6B 109.6 . . ? C7 C6 H6B 109.6 . . ? H6A C6 H6B 108.1 . . ? N4 C7 C6 112.2(3) . . ? N4 C7 H7A 109.2 . . ? C6 C7 H7A 109.2 . . ? N4 C7 H7B 109.2 . . ? C6 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? N4 C8 C9 108.5(3) . . ? N4 C8 H8A 110.0 . . ? C9 C8 H8A 110.0 . . ? N4 C8 H8B 110.0 . . ? C9 C8 H8B 110.0 . . ? H8A C8 H8B 108.4 . . ? C10 C9 C8 109.8(4) . . ? C10 C9 H9A 109.7 . . ? C8 C9 H9A 109.7 . . ? C10 C9 H9B 109.7 . . ? C8 C9 H9B 109.7 . . ? H9A C9 H9B 108.2 . . ? C9 C10 N1 113.9(3) . . ? C9 C10 H10A 108.8 . . ? N1 C10 H10A 108.8 . . ? C9 C10 H10B 108.8 . . ? N1 C10 H10B 108.8 . . ? H10A C10 H10B 107.7 . . ? C12 C11 N1 115.8(3) . . ? C12 C11 H11A 108.3 . . ? N1 C11 H11A 108.3 . . ? C12 C11 H11B 108.3 . . ? N1 C11 H11B 108.3 . . ? H11A C11 H11B 107.4 . . ? C17 C12 C13 118.8(4) . . ? C17 C12 C11 119.6(4) . . ? C13 C12 C11 121.1(4) . . ? C12 C13 C14 120.6(4) . . ? C12 C13 H13 119.7 . . ? C14 C13 H13 119.7 . . ? C15 C14 C13 120.0(5) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C14 C15 C16 120.4(5) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? C15 C16 C17 119.8(5) . . ? C15 C16 H16 120.1 . . ? C17 C16 H16 120.1 . . ? C12 C17 C16 120.3(5) . . ? C12 C17 H17 119.9 . . ? C16 C17 H17 119.9 . . ? N3 C21 N2 111.6(3) . . ? N3 C21 C41 107.2(3) . . ? N2 C21 C41 112.6(3) . . ? N3 C21 H21 108.4 . . ? N2 C21 H21 108.4 . . ? C41 C21 H21 108.4 . . ? N4 C41 C42 114.2(3) . . ? N4 C41 C21 109.3(3) . . ? C42 C41 C21 108.2(3) . . ? N4 C41 N1 106.4(3) . . ? C42 C41 N1 109.1(3) . . ? C21 C41 N1 109.5(3) . . ? C41 C42 H42A 109.5 . . ? C41 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? C41 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? Cl3 C50 Cl2 111.2(2) . . ? Cl3 C50 Cl1 110.6(2) . . ? Cl2 C50 Cl1 110.4(3) . . ? Cl3 C50 H50 105(3) . . ? Cl2 C50 H50 111(2) . . ? Cl1 C50 H50 109(2) . . ? Cl5 C60 Cl4 110.8(3) . . ? Cl5 C60 Cl6 110.3(2) . . ? Cl4 C60 Cl6 110.4(3) . . ? Cl5 C60 H60 115(3) . . ? Cl4 C60 H60 102(3) . . ? Cl6 C60 H60 108(3) . . ? Cl9 C70 Cl7 110.3(2) . . ? Cl9 C70 Cl8 110.0(3) . . ? Cl7 C70 Cl8 110.4(2) . . ? Cl9 C70 H70 108(2) . . ? Cl7 C70 H70 109(2) . . ? Cl8 C70 H70 109(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 C10 N1 C1 C2 -175.5(3) . . . . ? C11 N1 C1 C2 67.6(4) . . . . ? C41 N1 C1 C2 -54.0(4) . . . . ? C21 N2 C2 C1 -62.3(4) . . . . ? C3 N2 C2 C1 179.9(3) . . . . ? N1 C1 C2 N2 61.3(4) . . . . ? C2 N2 C3 C4 174.6(3) . . . . ? C21 N2 C3 C4 56.4(4) . . . . ? N2 C3 C4 C5 -52.0(5) . . . . ? C21 N3 C5 C4 -57.3(5) . . . . ? C6 N3 C5 C4 66.1(4) . . . . ? C3 C4 C5 N3 52.2(5) . . . . ? C21 N3 C6 C7 -59.5(4) . . . . ? C5 N3 C6 C7 178.1(3) . . . . ? C8 N4 C7 C6 177.3(4) . . . . ? C41 N4 C7 C6 -55.3(5) . . . . ? N3 C6 C7 N4 55.1(5) . . . . ? C7 N4 C8 C9 -170.0(3) . . . . ? C41 N4 C8 C9 65.4(4) . . . . ? N4 C8 C9 C10 -57.8(4) . . . . ? C8 C9 C10 N1 53.1(5) . . . . ? C1 N1 C10 C9 69.8(4) . . . . ? C11 N1 C10 C9 -170.6(3) . . . . ? C41 N1 C10 C9 -49.8(4) . . . . ? C1 N1 C11 C12 54.4(5) . . . . ? C10 N1 C11 C12 -62.5(4) . . . . ? C41 N1 C11 C12 175.5(3) . . . . ? N1 C11 C12 C17 -100.9(5) . . . . ? N1 C11 C12 C13 86.9(5) . . . . ? C17 C12 C13 C14 2.6(6) . . . . ? C11 C12 C13 C14 174.8(4) . . . . ? C12 C13 C14 C15 -0.7(7) . . . . ? C13 C14 C15 C16 -1.8(7) . . . . ? C14 C15 C16 C17 2.2(7) . . . . ? C13 C12 C17 C16 -2.2(6) . . . . ? C11 C12 C17 C16 -174.5(4) . . . . ? C15 C16 C17 C12 -0.2(7) . . . . ? C5 N3 C21 N2 62.0(4) . . . . ? C6 N3 C21 N2 -62.0(4) . . . . ? C5 N3 C21 C41 -174.2(3) . . . . ? C6 N3 C21 C41 61.8(4) . . . . ? C2 N2 C21 N3 -179.1(3) . . . . ? C3 N2 C21 N3 -61.4(4) . . . . ? C2 N2 C21 C41 60.3(4) . . . . ? C3 N2 C21 C41 177.9(3) . . . . ? C8 N4 C41 C42 60.7(4) . . . . ? C7 N4 C41 C42 -63.6(4) . . . . ? C8 N4 C41 C21 -177.9(3) . . . . ? C7 N4 C41 C21 57.9(4) . . . . ? C8 N4 C41 N1 -59.7(4) . . . . ? C7 N4 C41 N1 176.0(3) . . . . ? N3 C21 C41 N4 -61.1(4) . . . . ? N2 C21 C41 N4 62.1(4) . . . . ? N3 C21 C41 C42 63.9(4) . . . . ? N2 C21 C41 C42 -173.0(3) . . . . ? N3 C21 C41 N1 -177.3(3) . . . . ? N2 C21 C41 N1 -54.2(4) . . . . ? C1 N1 C41 N4 -68.7(4) . . . . ? C10 N1 C41 N4 49.7(4) . . . . ? C11 N1 C41 N4 168.9(3) . . . . ? C1 N1 C41 C42 167.6(3) . . . . ? C10 N1 C41 C42 -73.9(4) . . . . ? C11 N1 C41 C42 45.3(4) . . . . ? C1 N1 C41 C21 49.3(4) . . . . ? C10 N1 C41 C21 167.8(3) . . . . ? C11 N1 C41 C21 -73.0(4) . . . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.582 _refine_diff_density_min -0.486 _refine_diff_density_rms 0.109 #=========================================================================== #END data_fbo218 _database_code_CSD 172982 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H20 N4' _chemical_formula_sum 'C10 H20 N4' _chemical_formula_weight 196.30 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 'P 21/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 9.3721(4) _cell_length_b 7.8942(4) _cell_length_c 14.4579(7) _cell_angle_alpha 90.00 _cell_angle_beta 91.640(2) _cell_angle_gamma 90.00 _cell_volume 1069.23(9) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 4135 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 27.50 _exptl_crystal_description 'Prism' _exptl_crystal_colour 'Colourless' _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.219 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 0.077 _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 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 4135 _diffrn_reflns_av_R_equivalents 0.0303 _diffrn_reflns_av_sigmaI/netI 0.0503 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.56 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2448 _reflns_number_gt 1645 _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^)+(0.0425P)^2^+0.2244P] 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 0.008(2) _refine_ls_extinction_expression 'Fc^*^==kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2448 _refine_ls_number_parameters 189 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0782 _refine_ls_R_factor_gt 0.0423 _refine_ls_wR_factor_ref 0.1043 _refine_ls_wR_factor_gt 0.0897 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.013 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.001 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 0.61108(12) -0.00666(15) 0.12014(8) 0.0247(3) Uani 1 1 d . . . N2 N 0.49289(11) 0.10519(14) 0.28690(7) 0.0201(3) Uani 1 1 d . . . N3 N 0.47291(12) 0.39033(14) 0.22425(8) 0.0230(3) Uani 1 1 d . . . N4 N 0.39190(11) 0.14637(15) 0.08507(8) 0.0222(3) Uani 1 1 d . . . C1 C 0.55301(16) -0.12863(19) 0.18448(10) 0.0259(3) Uani 1 1 d . . . C2 C 0.56916(16) -0.05600(19) 0.28069(10) 0.0259(3) Uani 1 1 d . . . C3 C 0.50983(16) 0.17138(19) 0.38172(10) 0.0266(3) Uani 1 1 d . . . C4 C 0.43455(17) 0.3403(2) 0.39165(10) 0.0291(4) Uani 1 1 d . . . C5 C 0.48656(17) 0.46212(19) 0.31801(10) 0.0285(4) Uani 1 1 d . . . C6 C 0.32312(15) 0.3758(2) 0.19242(10) 0.0268(3) Uani 1 1 d . . . C7 C 0.31383(16) 0.3072(2) 0.09471(10) 0.0277(4) Uani 1 1 d . . . C21 C 0.54930(14) 0.22893(17) 0.22054(9) 0.0200(3) Uani 1 1 d . . . C41 C 0.54230(13) 0.15853(17) 0.12087(9) 0.0208(3) Uani 1 1 d . . . C42 C 0.62482(17) 0.2749(2) 0.05716(11) 0.0294(4) Uani 1 1 d . . . H1A H 0.4505(16) -0.1589(19) 0.1705(10) 0.0307(9) Uiso 1 1 d . . . H1B H 0.6056(16) -0.239(2) 0.1795(10) 0.0307(9) Uiso 1 1 d . . . H2A H 0.6749(16) -0.0424(19) 0.2972(10) 0.0307(9) Uiso 1 1 d . . . H2B H 0.5299(15) -0.136(2) 0.3265(10) 0.0307(9) Uiso 1 1 d . . . H3A H 0.6140(16) 0.1864(19) 0.3994(10) 0.0307(9) Uiso 1 1 d . . . H3B H 0.4710(15) 0.085(2) 0.4254(10) 0.0307(9) Uiso 1 1 d . . . H4A H 0.4574(15) 0.3877(19) 0.4549(11) 0.0307(9) Uiso 1 1 d . . . H4B H 0.3274(16) 0.3247(19) 0.3848(10) 0.0307(9) Uiso 1 1 d . . . H5A H 0.5893(16) 0.4873(19) 0.3313(10) 0.0307(9) Uiso 1 1 d . . . H5B H 0.4308(15) 0.570(2) 0.3180(10) 0.0307(9) Uiso 1 1 d . . . H6A H 0.2663(16) 0.299(2) 0.2346(10) 0.0307(9) Uiso 1 1 d . . . H6B H 0.2788(15) 0.491(2) 0.1952(10) 0.0307(9) Uiso 1 1 d . . . H7A H 0.3539(15) 0.392(2) 0.0510(11) 0.0307(9) Uiso 1 1 d . . . H7B H 0.2106(16) 0.2836(19) 0.0761(10) 0.0307(9) Uiso 1 1 d . . . H21 H 0.6542(16) 0.2520(19) 0.2378(10) 0.0307(9) Uiso 1 1 d . . . H42A H 0.7277(16) 0.2657(19) 0.0723(10) 0.0307(9) Uiso 1 1 d . . . H42B H 0.6092(15) 0.2390(19) -0.0096(11) 0.0307(9) Uiso 1 1 d . . . H42C H 0.5946(15) 0.399(2) 0.0629(10) 0.0307(9) Uiso 1 1 d . . . HN1 H 0.6090(15) -0.046(2) 0.0615(11) 0.0307(9) Uiso 1 1 d . . . HN4 H 0.3486(16) 0.066(2) 0.1205(10) 0.0307(9) 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 0.0237(6) 0.0272(7) 0.0233(7) -0.0058(5) 0.0021(5) 0.0019(5) N2 0.0242(6) 0.0188(6) 0.0175(6) 0.0006(5) 0.0007(5) 0.0002(5) N3 0.0261(6) 0.0196(6) 0.0234(6) -0.0022(5) 0.0018(5) 0.0000(5) N4 0.0205(6) 0.0245(7) 0.0216(6) 0.0003(5) -0.0010(5) -0.0009(5) C1 0.0257(8) 0.0213(8) 0.0305(8) -0.0039(6) -0.0019(6) 0.0041(6) C2 0.0285(8) 0.0223(8) 0.0267(8) 0.0021(6) -0.0027(6) 0.0022(6) C3 0.0314(8) 0.0315(8) 0.0170(7) -0.0014(6) -0.0010(6) -0.0040(7) C4 0.0340(9) 0.0313(8) 0.0221(8) -0.0076(6) 0.0041(6) -0.0043(7) C5 0.0331(9) 0.0223(8) 0.0302(9) -0.0081(7) 0.0043(7) -0.0018(7) C6 0.0260(8) 0.0249(8) 0.0295(9) -0.0005(7) 0.0006(6) 0.0054(6) C7 0.0271(8) 0.0285(8) 0.0275(8) 0.0051(7) -0.0013(6) 0.0029(6) C21 0.0173(6) 0.0195(7) 0.0233(8) -0.0003(6) 0.0018(5) -0.0011(5) C41 0.0184(7) 0.0237(7) 0.0202(7) -0.0016(6) 0.0014(5) -0.0008(6) C42 0.0290(8) 0.0364(9) 0.0229(8) -0.0002(7) 0.0055(7) -0.0066(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C41 1.4548(17) . ? N1 C1 1.4551(18) . ? N2 C2 1.4636(17) . ? N2 C3 1.4713(17) . ? N2 C21 1.4777(17) . ? N3 C21 1.4632(17) . ? N3 C6 1.4693(18) . ? N3 C5 1.4714(18) . ? N4 C7 1.4737(18) . ? N4 C41 1.4906(16) . ? C1 C2 1.508(2) . ? C3 C4 1.517(2) . ? C4 C5 1.525(2) . ? C6 C7 1.513(2) . ? C21 C41 1.5441(19) . ? C41 C42 1.527(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 C41 N1 C1 114.49(11) . . ? C2 N2 C3 109.03(11) . . ? C2 N2 C21 110.51(10) . . ? C3 N2 C21 109.83(11) . . ? C21 N3 C6 112.63(11) . . ? C21 N3 C5 109.84(11) . . ? C6 N3 C5 112.06(11) . . ? C7 N4 C41 112.26(11) . . ? N1 C1 C2 107.97(12) . . ? N2 C2 C1 110.54(12) . . ? N2 C3 C4 111.23(12) . . ? C3 C4 C5 109.23(12) . . ? N3 C5 C4 112.29(12) . . ? N3 C6 C7 110.44(12) . . ? N4 C7 C6 112.42(12) . . ? N3 C21 N2 111.54(10) . . ? N3 C21 C41 109.87(11) . . ? N2 C21 C41 111.20(11) . . ? N1 C41 N4 110.77(11) . . ? N1 C41 C42 107.64(11) . . ? N4 C41 C42 108.64(11) . . ? N1 C41 C21 108.81(11) . . ? N4 C41 C21 111.20(10) . . ? C42 C41 C21 109.72(11) . . ? 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 C41 N1 C1 C2 -59.25(15) . . . . ? C3 N2 C2 C1 179.48(12) . . . . ? C21 N2 C2 C1 -59.72(15) . . . . ? N1 C1 C2 N2 59.50(15) . . . . ? C2 N2 C3 C4 179.10(12) . . . . ? C21 N2 C3 C4 57.87(15) . . . . ? N2 C3 C4 C5 -53.97(16) . . . . ? C21 N3 C5 C4 -56.08(15) . . . . ? C6 N3 C5 C4 69.91(16) . . . . ? C3 C4 C5 N3 53.30(17) . . . . ? C21 N3 C6 C7 -57.44(15) . . . . ? C5 N3 C6 C7 178.10(12) . . . . ? C41 N4 C7 C6 -52.55(16) . . . . ? N3 C6 C7 N4 54.02(16) . . . . ? C6 N3 C21 N2 -66.24(14) . . . . ? C5 N3 C21 N2 59.42(14) . . . . ? C6 N3 C21 C41 57.54(14) . . . . ? C5 N3 C21 C41 -176.79(11) . . . . ? C2 N2 C21 N3 178.96(11) . . . . ? C3 N2 C21 N3 -60.71(14) . . . . ? C2 N2 C21 C41 55.93(14) . . . . ? C3 N2 C21 C41 176.26(11) . . . . ? C1 N1 C41 N4 -66.82(14) . . . . ? C1 N1 C41 C42 174.55(12) . . . . ? C1 N1 C41 C21 55.71(14) . . . . ? C7 N4 C41 N1 173.45(11) . . . . ? C7 N4 C41 C42 -68.53(14) . . . . ? C7 N4 C41 C21 52.33(15) . . . . ? N3 C21 C41 N1 -176.46(10) . . . . ? N2 C21 C41 N1 -52.48(14) . . . . ? N3 C21 C41 N4 -54.20(14) . . . . ? N2 C21 C41 N4 69.79(14) . . . . ? N3 C21 C41 C42 66.01(14) . . . . ? N2 C21 C41 C42 -170.00(11) . . . . ? 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 HN1 N4 0.903(16) 2.262(16) 3.1647(17) 178.9(13) 3_655 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.174 _refine_diff_density_min -0.177 _refine_diff_density_rms 0.040