# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 1999 # CCDC Number: 207/368 data_93mh1 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C8 H14 N8 O4' _chemical_formula_weight 286.27 _chemical_melting_point ? _chemical_compound_source ? 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' 'O' 'O' 0.0106 0.0060 '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/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 7.2650(6) _cell_length_b 12.408(2) _cell_length_c 14.529(2) _cell_angle_alpha 90.00 _cell_angle_beta 96.350(13) _cell_angle_gamma 90.00 _cell_volume 1301.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.461 _exptl_crystal_density_method ? _exptl_crystal_F_000 600 _exptl_absorpt_coefficient_mu 0.119 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.70930 _diffrn_radiation_type ? _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2131 _diffrn_reflns_av_R_equivalents 0.0126 _diffrn_reflns_av_sigmaI/netI 0.0140 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 23.92 _reflns_number_total 2045 _reflns_number_observed 1410 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 4 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 F _refine_ls_matrix_type full _refine_ls_weighting_scheme '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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0586(73) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2041 _refine_ls_number_parameters 220 _refine_ls_number_restraints 10 _refine_ls_R_factor_all 0.0615 _refine_ls_R_factor_obs 0.0404 _refine_ls_wR_factor_all 0.1836 _refine_ls_wR_factor_obs 0.1489 _refine_ls_goodness_of_fit_all 1.244 _refine_ls_goodness_of_fit_obs 1.391 _refine_ls_restrained_S_all 1.395 _refine_ls_restrained_S_obs 1.390 _refine_ls_shift/esd_max 0.037 _refine_ls_shift/esd_mean 0.005 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group N1 N 0.1372(2) -0.00512(12) 0.65890(11) 0.0351(5) Uani 1 d . . N2 N 0.1579(2) -0.06724(13) 0.58387(11) 0.0419(5) Uani 1 d . . N3 N 0.2466(3) -0.01648(13) 0.52485(11) 0.0427(5) Uani 1 d . . N4 N 0.2852(2) 0.08114(13) 0.56143(11) 0.0376(5) Uani 1 d D . N5 N 0.3525(2) -0.00263(12) 0.84343(11) 0.0341(5) Uani 1 d . . N6 N 0.3337(2) -0.06348(13) 0.91921(11) 0.0401(5) Uani 1 d . . N7 N 0.2430(3) -0.01204(13) 0.97725(11) 0.0424(5) Uani 1 d . . N8 N 0.2006(2) 0.08397(12) 0.93893(10) 0.0354(5) Uani 1 d D . C1 C 0.2190(2) 0.08768(15) 0.64388(12) 0.0304(5) Uani 1 d . . C2 C 0.2332(2) 0.18637(14) 0.70076(12) 0.0278(5) Uani 1 d . . C3 C 0.2239(2) 0.28411(14) 0.65388(12) 0.0316(5) Uani 1 d . . H3 H 0.2114(2) 0.28409(14) 0.58948(12) 0.038 Uiso 1 calc R . C4 C 0.2328(2) 0.38110(14) 0.70036(13) 0.0335(5) Uani 1 d . . H4 H 0.2273(2) 0.44552(14) 0.66744(13) 0.040 Uiso 1 calc R . C5 C 0.2499(3) 0.38232(14) 0.79585(13) 0.0337(5) Uani 1 d . . H5 H 0.2553(3) 0.44749(14) 0.82766(13) 0.040 Uiso 1 calc R . C6 C 0.2590(2) 0.28594(14) 0.84394(12) 0.0316(5) Uani 1 d . . H6 H 0.2706(2) 0.28718(14) 0.90832(12) 0.038 Uiso 1 calc R . C7 C 0.2514(2) 0.18679(14) 0.79820(12) 0.0275(5) Uani 1 d . . C8 C 0.2675(2) 0.08953(14) 0.85644(12) 0.0284(5) Uani 1 d . . O1 O 0.0281(2) 0.22271(11) 1.04316(10) 0.0448(5) Uani 1 d D . O2 O 0.4540(2) 0.21468(12) 0.45316(10) 0.0484(5) Uani 1 d D . O3 O 0.4414(2) 0.14234(13) 0.26777(11) 0.0474(5) Uani 1 d D . O4 O 0.0536(2) 0.14811(13) 0.22594(11) 0.0485(5) Uani 1 d D . H1 H 0.3564(31) 0.1319(18) 0.5284(15) 0.058 Uiso 1 d D . H2 H 0.1391(31) 0.1383(18) 0.9769(14) 0.058 Uiso 1 d D . H1A H 0.0138(38) 0.1874(20) 1.1019(16) 0.072(8) Uiso 1 d D . H1B H 0.0802(35) 0.2918(17) 1.0541(18) 0.065(8) Uiso 1 d D . H2A H 0.4138(43) 0.2893(18) 0.4490(21) 0.091(10) Uiso 1 d D . H2B H 0.4666(40) 0.1854(21) 0.3943(16) 0.077(9) Uiso 1 d D . H3A H 0.4903(36) 0.0906(20) 0.2328(17) 0.078(9) Uiso 1 d D . H3B H 0.4759(38) 0.2108(21) 0.2489(17) 0.119(12) Uiso 1 d D . H4A H 0.1853(35) 0.1403(27) 0.2412(17) 0.113(12) Uiso 1 d D . H4B H 0.0067(32) 0.0923(19) 0.2553(16) 0.058(7) Uiso 1 d 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 0.0441(10) 0.0269(9) 0.0344(10) -0.0029(7) 0.0051(7) -0.0025(7) N2 0.0580(11) 0.0315(10) 0.0360(10) -0.0069(8) 0.0046(8) -0.0020(8) N3 0.0655(12) 0.0315(9) 0.0316(9) -0.0066(7) 0.0074(8) 0.0007(8) N4 0.0524(11) 0.0307(9) 0.0311(10) -0.0039(7) 0.0106(7) -0.0021(7) N5 0.0451(10) 0.0236(9) 0.0339(9) 0.0033(7) 0.0061(7) 0.0038(7) N6 0.0548(11) 0.0265(9) 0.0386(10) 0.0075(7) 0.0039(8) 0.0033(8) N7 0.0618(12) 0.0297(9) 0.0360(10) 0.0085(7) 0.0067(8) 0.0001(8) N8 0.0544(10) 0.0255(8) 0.0275(9) 0.0032(7) 0.0098(7) 0.0016(7) C1 0.0361(10) 0.0278(10) 0.0274(10) -0.0008(8) 0.0030(7) 0.0017(8) C2 0.0311(10) 0.0231(10) 0.0295(11) 0.0004(8) 0.0048(7) -0.0010(7) C3 0.0406(11) 0.0284(10) 0.0261(10) 0.0028(8) 0.0043(8) 0.0003(8) C4 0.0395(11) 0.0221(10) 0.0394(12) 0.0045(8) 0.0060(8) 0.0010(8) C5 0.0396(11) 0.0248(10) 0.0371(11) -0.0034(8) 0.0064(8) 0.0003(8) C6 0.0387(11) 0.0281(11) 0.0285(10) -0.0025(8) 0.0059(8) -0.0017(8) C7 0.0305(9) 0.0263(10) 0.0263(10) 0.0012(8) 0.0056(7) -0.0002(7) C8 0.0374(10) 0.0246(9) 0.0230(9) -0.0011(8) 0.0024(7) -0.0029(8) O1 0.0652(11) 0.0328(9) 0.0380(9) -0.0073(7) 0.0122(7) -0.0092(7) O2 0.0751(11) 0.0376(9) 0.0349(9) 0.0064(7) 0.0162(7) 0.0101(7) O3 0.0587(10) 0.0399(9) 0.0467(9) -0.0039(7) 0.0195(7) 0.0004(7) O4 0.0559(11) 0.0401(9) 0.0509(10) 0.0089(7) 0.0125(7) -0.0009(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 C1 1.325(2) . ? N1 N2 1.357(2) . ? N2 N3 1.292(2) . ? N3 N4 1.340(2) . ? N4 C1 1.342(2) . ? N5 C8 1.323(2) . ? N5 N6 1.354(2) . ? N6 N7 1.295(2) . ? N7 N8 1.336(2) . ? N8 C8 1.344(2) . ? C1 C2 1.475(2) . ? C2 C3 1.389(2) . ? C2 C7 1.407(3) . ? C3 C4 1.378(2) . ? C4 C5 1.379(3) . ? C5 C6 1.383(2) . ? C6 C7 1.396(2) . ? C7 C8 1.471(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 C1 N1 N2 105.7(2) . . ? N3 N2 N1 111.3(2) . . ? N2 N3 N4 105.97(15) . . ? N3 N4 C1 109.2(2) . . ? C8 N5 N6 105.96(15) . . ? N7 N6 N5 111.0(2) . . ? N6 N7 N8 106.16(15) . . ? N7 N8 C8 109.2(2) . . ? N1 C1 N4 107.8(2) . . ? N1 C1 C2 129.4(2) . . ? N4 C1 C2 122.7(2) . . ? C3 C2 C7 118.96(14) . . ? C3 C2 C1 117.0(2) . . ? C7 C2 C1 124.05(14) . . ? C4 C3 C2 121.7(2) . . ? C3 C4 C5 119.78(15) . . ? C4 C5 C6 119.5(2) . . ? C5 C6 C7 121.6(2) . . ? C6 C7 C2 118.45(14) . . ? C6 C7 C8 116.9(2) . . ? C2 C7 C8 124.63(14) . . ? N5 C8 N8 107.7(2) . . ? N5 C8 C7 129.5(2) . . ? N8 C8 C7 122.8(2) . . ? _refine_diff_density_max 0.202 _refine_diff_density_min -0.171 _refine_diff_density_rms 0.048 data_93kcm2 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C20 H16 N16' _chemical_formula_weight 480.49 _chemical_melting_point ? _chemical_compound_source ? 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 Tetragonal _symmetry_space_group_name_H-M I41cd loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-y, x+1/2, z+1/4' 'y+1/2, -x, z+3/4' 'x, -y, z+1/2' '-x+1/2, y+1/2, z' '-y, -x+1/2, z+3/4' 'y+1/2, x, z+1/4' 'x+1/2, y+1/2, z+1/2' '-x+1, -y+1, z+1' '-y+1/2, x+1, z+3/4' 'y+1, -x+1/2, z+5/4' 'x+1/2, -y+1/2, z+1' '-x+1, y+1, z+1/2' '-y+1/2, -x+1, z+5/4' 'y+1, x+1/2, z+3/4' _cell_length_a 24.513(2) _cell_length_b 24.513(2) _cell_length_c 7.0350(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4227.2(8) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.510 _exptl_crystal_density_method ? _exptl_crystal_F_000 1984 _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1771 _diffrn_reflns_av_R_equivalents 0.0371 _diffrn_reflns_av_sigmaI/netI 0.0444 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 23.97 _reflns_number_total 904 _reflns_number_observed 692 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 F _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0585P)^2^+0.5602P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0038(6) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.50(551) _refine_ls_number_reflns 904 _refine_ls_number_parameters 164 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0664 _refine_ls_R_factor_obs 0.0427 _refine_ls_wR_factor_all 0.1024 _refine_ls_wR_factor_obs 0.0907 _refine_ls_goodness_of_fit_all 1.092 _refine_ls_goodness_of_fit_obs 1.142 _refine_ls_restrained_S_all 1.092 _refine_ls_restrained_S_obs 1.141 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group N1 N 0.1888(2) 0.44766(14) 0.1223(6) 0.0372(10) Uani 1 d . . N2 N 0.2198(2) 0.4928(2) 0.1006(6) 0.0488(13) Uani 1 d . . N3 N 0.1903(2) 0.5330(2) 0.1634(7) 0.0509(13) Uani 1 d . . N4 N 0.1404(2) 0.51488(14) 0.2252(7) 0.0453(12) Uani 1 d . . N5 N 0.20361(13) 0.3527(2) 0.3715(6) 0.0353(10) Uani 1 d . . N6 N 0.2314(2) 0.3320(2) 0.5218(7) 0.0458(11) Uani 1 d . . N7 N 0.1959(2) 0.3215(2) 0.6503(8) 0.0492(12) Uani 1 d . . N8 N 0.1449(2) 0.33444(15) 0.5909(6) 0.0417(11) Uani 1 d . . C1 C 0.1411(2) 0.4620(2) 0.1973(7) 0.0343(12) Uani 1 d . . C2 C 0.0957(2) 0.4238(2) 0.2266(7) 0.0343(12) Uani 1 d . . C3 C 0.0447(2) 0.4399(2) 0.1609(9) 0.0510(15) Uani 1 d . . H3A H 0.0404(2) 0.4745(2) 0.1085(9) 0.061 Uiso 1 calc R . C4 C 0.0006(2) 0.4055(2) 0.1722(10) 0.0567(15) Uani 1 d . . H4A H -0.0335(2) 0.4173(2) 0.1320(10) 0.068 Uiso 1 calc R . C5 C 0.0067(2) 0.3537(2) 0.2426(10) 0.055(2) Uani 1 d . . H5A H -0.0229(2) 0.3300(2) 0.2450(10) 0.065 Uiso 1 calc R . C6 C 0.0573(2) 0.3367(2) 0.3105(8) 0.0435(13) Uani 1 d . . H6A H 0.0612(2) 0.3016(2) 0.3590(8) 0.052 Uiso 1 calc R . C7 C 0.1020(2) 0.3715(2) 0.3066(8) 0.0357(12) Uani 1 d . . C8 C 0.1505(2) 0.3538(2) 0.4165(8) 0.0337(11) Uani 1 d . . C9 C 0.2351(2) 0.3613(2) 0.1969(8) 0.0491(14) Uani 1 d . . H9A H 0.2439(2) 0.3260(2) 0.1422(8) 0.059 Uiso 1 calc R . H9B H 0.2692(2) 0.3791(2) 0.2294(8) 0.059 Uiso 1 calc R . C10 C 0.2063(2) 0.3950(2) 0.0499(8) 0.0433(13) Uani 1 d . . H10A H 0.2305(2) 0.4007(2) -0.0573(8) 0.052 Uiso 1 calc R . H10B H 0.1747(2) 0.3751(2) 0.0045(8) 0.052 Uiso 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 N1 0.044(2) 0.034(2) 0.033(2) -0.002(2) 0.003(2) -0.008(2) N2 0.054(3) 0.046(3) 0.047(3) 0.000(2) 0.004(2) -0.017(2) N3 0.061(3) 0.041(2) 0.051(3) 0.004(2) 0.004(3) -0.017(2) N4 0.052(3) 0.033(2) 0.051(3) 0.000(2) 0.004(2) -0.002(2) N5 0.033(2) 0.034(2) 0.038(3) 0.003(2) 0.001(2) -0.002(2) N6 0.042(2) 0.049(3) 0.047(3) 0.006(2) -0.006(3) 0.001(2) N7 0.048(3) 0.053(3) 0.046(3) 0.008(2) -0.006(3) -0.003(2) N8 0.047(3) 0.038(2) 0.040(3) 0.008(2) 0.002(2) -0.006(2) C1 0.040(3) 0.036(2) 0.027(3) 0.003(2) 0.000(2) -0.002(2) C2 0.032(3) 0.031(2) 0.040(3) 0.000(2) -0.003(2) 0.000(2) C3 0.049(3) 0.042(3) 0.063(4) 0.008(3) -0.014(3) 0.001(2) C4 0.042(3) 0.053(3) 0.075(4) 0.006(3) -0.022(3) 0.000(3) C5 0.033(3) 0.061(3) 0.069(4) 0.006(3) -0.009(3) -0.013(3) C6 0.047(3) 0.037(3) 0.046(4) 0.002(2) -0.001(3) -0.007(2) C7 0.033(2) 0.037(3) 0.037(3) 0.000(2) 0.003(2) -0.004(2) C8 0.035(2) 0.031(2) 0.035(3) 0.001(3) 0.003(2) -0.004(2) C9 0.041(3) 0.058(3) 0.049(4) 0.000(3) 0.011(3) 0.007(3) C10 0.049(3) 0.046(3) 0.035(3) -0.002(3) 0.012(3) -0.003(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 N2 1.351(5) . ? N1 C1 1.328(6) . ? N1 C10 1.453(6) . ? N2 N3 1.300(6) . ? N3 N4 1.372(6) . ? N4 C1 1.312(5) . ? N5 C8 1.340(5) . ? N5 N6 1.356(6) . ? N5 C9 1.466(7) . ? N6 N7 1.281(6) . ? N7 N8 1.354(5) . ? N8 C8 1.323(6) . ? C1 C2 1.469(6) . ? C2 C3 1.390(6) . ? C2 C7 1.407(6) . ? C3 C4 1.374(7) . ? C4 C5 1.370(7) . ? C5 C6 1.392(7) . ? C6 C7 1.390(6) . ? C7 C8 1.483(7) . ? C9 C10 1.501(7) . ? 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 N2 N1 C1 108.9(4) . . ? N2 N1 C10 121.4(4) . . ? C1 N1 C10 129.3(4) . . ? N3 N2 N1 105.7(3) . . ? N2 N3 N4 110.9(3) . . ? C1 N4 N3 105.2(4) . . ? C8 N5 N6 108.1(4) . . ? C8 N5 C9 135.0(4) . . ? N6 N5 C9 116.3(4) . . ? N7 N6 N5 106.6(4) . . ? N6 N7 N8 111.2(4) . . ? C8 N8 N7 106.0(4) . . ? N4 C1 N1 109.4(4) . . ? N4 C1 C2 126.8(4) . . ? N1 C1 C2 123.6(4) . . ? C3 C2 C7 119.4(4) . . ? C3 C2 C1 117.0(4) . . ? C7 C2 C1 123.6(4) . . ? C4 C3 C2 120.9(5) . . ? C5 C4 C3 120.3(5) . . ? C4 C5 C6 119.9(5) . . ? C5 C6 C7 120.8(5) . . ? C6 C7 C2 118.7(4) . . ? C6 C7 C8 116.3(4) . . ? C2 C7 C8 124.2(4) . . ? N8 C8 N5 108.2(4) . . ? N8 C8 C7 120.4(4) . . ? N5 C8 C7 131.4(5) . . ? N5 C9 C10 114.1(4) . . ? N1 C10 C9 112.7(5) . . ? _refine_diff_density_max 0.141 _refine_diff_density_min -0.137 _refine_diff_density_rms 0.036 data_94mh4 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C12 H12 Br2 N8' _chemical_formula_weight 428.12 _chemical_melting_point ? _chemical_compound_source ? 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' '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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' '-x, -y, -z' '-x, y, -z-1/2' '-x+1/2, -y+1/2, -z' '-x+1/2, y+1/2, -z-1/2' _cell_length_a 15.959(3) _cell_length_b 11.370(2) _cell_length_c 8.9740(10) _cell_angle_alpha 90.00 _cell_angle_beta 102.820(10) _cell_angle_gamma 90.00 _cell_volume 1587.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.791 _exptl_crystal_density_method ? _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 5.115 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1292 _diffrn_reflns_av_R_equivalents 0.0496 _diffrn_reflns_av_sigmaI/netI 0.0622 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 23.98 _reflns_number_total 1245 _reflns_number_observed 814 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 F _refine_ls_matrix_type full _refine_ls_weighting_scheme '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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0147(20) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1245 _refine_ls_number_parameters 107 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1044 _refine_ls_R_factor_obs 0.0674 _refine_ls_wR_factor_all 0.1678 _refine_ls_wR_factor_obs 0.1566 _refine_ls_goodness_of_fit_all 1.231 _refine_ls_goodness_of_fit_obs 1.452 _refine_ls_restrained_S_all 1.231 _refine_ls_restrained_S_obs 1.452 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Br1 Br 0.39221(6) 0.35201(8) 0.05987(10) 0.0835(6) Uani 1 d . . N1 N 0.3856(3) 0.2852(5) 0.4838(6) 0.0473(14) Uani 1 d . . N2 N 0.3193(3) 0.2972(5) 0.3657(6) 0.0458(13) Uani 1 d . . N3 N 0.2747(4) 0.1982(5) 0.3278(6) 0.0566(15) Uani 1 d . . N4 N 0.3137(4) 0.1170(5) 0.4237(7) 0.055(2) Uani 1 d . . C1 C 0.3663(4) 0.4525(6) 0.2200(8) 0.060(2) Uani 1 d . . H111 H 0.4173(4) 0.4598(6) 0.3017(8) 0.073 Uiso 1 calc R . H112 H 0.3513(4) 0.5304(6) 0.1786(8) 0.073 Uiso 1 calc R . C2 C 0.2956(4) 0.4067(6) 0.2831(8) 0.055(2) Uani 1 d . . H121 H 0.2800(4) 0.4645(6) 0.3517(8) 0.066 Uiso 1 calc R . H122 H 0.2458(4) 0.3933(6) 0.2006(8) 0.066 Uiso 1 calc R . C3 C 0.3803(4) 0.1717(5) 0.5173(7) 0.044(2) Uani 1 d . . C4 C 0.5000 0.1712(7) 0.7500 0.039(2) Uani 1 d S . C5 C 0.4409(4) 0.1099(5) 0.6386(7) 0.0373(14) Uani 1 d . . C6 C 0.4408(5) -0.0135(6) 0.6403(8) 0.051(2) Uani 1 d . . C7 C 0.5000 -0.0726(8) 0.7500 0.055(3) Uani 1 d S . H41 H 0.5000 0.2588(93) 0.7500 0.065 Uiso 1 d S . H61 H 0.3905(37) -0.0581(71) 0.5525(70) 0.065 Uiso 1 d . . H71 H 0.5000 -0.1523(88) 0.7500 0.065 Uiso 1 d S . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.1228(10) 0.0697(7) 0.0604(7) 0.0149(4) 0.0253(5) 0.0284(5) N1 0.051(3) 0.041(3) 0.041(3) 0.003(2) -0.008(2) 0.001(2) N2 0.043(3) 0.043(3) 0.046(3) 0.001(3) -0.002(2) 0.000(2) N3 0.057(3) 0.051(3) 0.051(3) 0.003(3) -0.010(3) -0.010(3) N4 0.061(3) 0.042(3) 0.056(4) 0.000(3) -0.002(3) -0.010(3) C1 0.071(5) 0.050(4) 0.054(4) 0.007(3) 0.000(4) 0.013(4) C2 0.052(4) 0.055(4) 0.052(4) 0.010(3) -0.004(3) 0.015(3) C3 0.055(4) 0.041(4) 0.036(3) -0.004(3) 0.007(3) -0.005(3) C4 0.040(5) 0.030(5) 0.046(5) 0.000 0.008(4) 0.000 C5 0.047(3) 0.028(3) 0.036(3) 0.000(2) 0.007(3) 0.002(3) C6 0.067(4) 0.040(4) 0.043(4) -0.004(3) 0.004(3) -0.011(3) C7 0.079(7) 0.028(5) 0.050(6) 0.000 -0.001(5) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C1 1.951(7) . ? N1 N2 1.328(6) . ? N1 C3 1.332(8) . ? N2 N3 1.335(8) . ? N2 C2 1.456(8) . ? N3 N4 1.319(8) . ? N4 C3 1.351(8) . ? C1 C2 1.466(10) . ? C3 C5 1.465(9) . ? C4 C5 1.399(7) . ? C4 C5 1.399(7) 6_657 ? C5 C6 1.404(9) . ? C6 C7 1.378(8) . ? C7 C6 1.378(8) 6_657 ? 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 N2 N1 C3 101.5(5) . . ? N1 N2 N3 113.7(5) . . ? N1 N2 C2 124.4(5) . . ? N3 N2 C2 121.9(5) . . ? N4 N3 N2 106.0(5) . . ? N3 N4 C3 106.0(5) . . ? C2 C1 Br1 112.5(5) . . ? N2 C2 C1 111.4(5) . . ? N1 C3 N4 112.7(6) . . ? N1 C3 C5 124.6(6) . . ? N4 C3 C5 122.7(6) . . ? C5 C4 C5 120.2(7) . 6_657 ? C4 C5 C6 119.5(6) . . ? C4 C5 C3 121.4(6) . . ? C6 C5 C3 119.1(6) . . ? C7 C6 C5 119.5(7) . . ? C6 C7 C6 121.7(9) 6_657 . ? _refine_diff_density_max 1.410 _refine_diff_density_min -0.692 _refine_diff_density_rms 0.163