# Copyright The Royal Society of Chemistry, 1999 # CCDC Number: 207/314 data_1 #----------------------------------------------------------------------------- _audit_creation_date '21-MAY-98 19:59:12' _audit_creation_method 'from TEXRAY.INF file' _audit_update_record ? #----------------------------------------------------------------------------- _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'TEXSAN' _computing_structure_solution 'MITHRIL (Gilmore, 1984)' _computing_structure_refinement 'TEXSAN' _computing_publication_material 'TEXSAN' _computing_molecular_graphics 'ORTEP (Johnson, 1965)' #----------------------------------------------------------------------------- _chemical_name_common ? _chemical_formula_weight 187.24 _chemical_formula_analytical ? _chemical_formula_sum 'C11 H13 N3 ' _chemical_formula_moiety 'C11 H13 N3 ' _chemical_formula_structural ? _chemical_melting_point ? #----------------------------------------------------------------------------- _cell_length_a 10.448(7) _cell_length_b 8.178(5) _cell_length_c 24.001(4) _cell_angle_alpha 90 _cell_angle_beta 101.14(2) _cell_angle_gamma 90 _cell_volume 2012(1) _cell_formula_units_Z 8 _cell_measurement_temperature 295.2 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 18.4 _cell_measurement_theta_max 19.9 #----------------------------------------------------------------------------- _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/C ' _symmetry_Int_Tables_number 14 _symmetry_space_group_name_Hall ? 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' #----------------------------------------------------------------------------- _exptl_crystal_description 'prism' _exptl_crystal_colour 'red' _exptl_crystal_size_max 0.360 _exptl_crystal_size_mid 0.460 _exptl_crystal_size_min 0.880 _exptl_crystal_density_diffrn 1.236 _exptl_crystal_density_meas 'not measured' _exptl_crystal_F_000 800.00 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type 'none' _exptl_special_details ? #----------------------------------------------------------------------------- _diffrn_special_details ? _diffrn_ambient_temperature 295.2 _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device 'Rigaku AFC5S' _diffrn_measurement_method \w-2\q _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% -2.50 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? ? ? ? ? ? ? _diffrn_reflns_number 5206 _reflns_number_total 5206 _reflns_number_observed 2206 _reflns_observed_criterion >2.0sigma(I) _diffrn_reflns_av_R_equivalents 0.00 _diffrn_reflns_av_sigmaI/netI 0.000 _diffrn_reflns_limit_h_min ? _diffrn_reflns_limit_h_max ? _diffrn_reflns_limit_k_min ? _diffrn_reflns_limit_k_max ? _diffrn_reflns_limit_l_min ? _diffrn_reflns_limit_l_max ? _diffrn_reflns_theta_min 0.00 _diffrn_reflns_theta_max 0.00 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 -0.00924 _diffrn_orient_matrix_UB_12 -0.09106 _diffrn_orient_matrix_UB_13 -0.02830 _diffrn_orient_matrix_UB_21 -0.01617 _diffrn_orient_matrix_UB_22 0.08146 _diffrn_orient_matrix_UB_23 -0.03165 _diffrn_orient_matrix_UB_31 0.09576 _diffrn_orient_matrix_UB_32 0.00497 _diffrn_orient_matrix_UB_33 0.00028 #----------------------------------------------------------------------------- loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 88 0.002 0.002 'International Tables Vol IV Table 2.2A' H 0 104 0.000 0.000 'International Tables Vol IV Table 2.2A' N 0 24 0.004 0.003 'International Tables Vol IV Table 2.2A' #----------------------------------------------------------------------------- loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom N(1) 0.6430(2) 0.1483(3) 0.4398(1) 0.042(1) 1.000 Uani . . N(2) 0.6254(3) -0.0218(3) 0.4341(1) 0.049(1) 1.000 Uani . . N(3) 0.6607(3) 0.1608(3) 0.5388(1) 0.050(1) 1.000 Uani . . N(4) 0.2201(3) 0.2364(3) -0.0857(1) 0.047(1) 1.000 Uani . . N(5) 0.3445(2) 0.3031(4) -0.0665(1) 0.056(1) 1.000 Uani . . N(6) 0.1395(3) 0.2904(4) -0.0030(1) 0.055(1) 1.000 Uani . . C(1) 0.6595(3) 0.2345(4) 0.4915(1) 0.044(1) 1.000 Uani . . C(2) 0.6688(3) 0.4029(4) 0.4751(2) 0.051(2) 1.000 Uani . . C(3) 0.6526(3) 0.4154(4) 0.4175(2) 0.047(2) 1.000 Uani . . C(4) 0.6479(4) 0.5604(4) 0.3850(2) 0.062(2) 1.000 Uani . . C(5) 0.6298(4) 0.5789(5) 0.3278(2) 0.070(2) 1.000 Uani . . C(6) 0.6151(4) 0.4598(6) 0.2843(2) 0.067(2) 1.000 Uani . . C(7) 0.6122(4) 0.2941(5) 0.2899(2) 0.062(2) 1.000 Uani . . C(8) 0.6210(3) 0.1961(4) 0.3390(2) 0.051(2) 1.000 Uani . . C(9) 0.6364(3) 0.2493(4) 0.3940(1) 0.043(1) 1.000 Uani . . C(10) 0.6870(4) 0.2658(5) 0.5894(2) 0.067(2) 1.000 Uani . . C(11) 0.7087(5) 0.1671(6) 0.6427(2) 0.088(3) 1.000 Uani . . C(12) 0.1203(3) 0.2335(4) -0.0538(2) 0.049(2) 1.000 Uani . . C(13) 0.0135(3) 0.1565(5) -0.0915(2) 0.059(2) 1.000 Uani . . C(14) 0.0483(3) 0.1155(4) -0.1413(2) 0.055(2) 1.000 Uani . . C(15) -0.0277(4) 0.0314(6) -0.1883(2) 0.078(2) 1.000 Uani . . C(16) 0.0044(4) -0.0138(6) -0.2383(2) 0.083(3) 1.000 Uani . . C(17) 0.1210(5) 0.0094(6) -0.2583(2) 0.078(2) 1.000 Uani . . C(18) 0.2324(4) 0.0821(5) -0.2314(2) 0.069(2) 1.000 Uani . . C(19) 0.2621(3) 0.1542(4) -0.1774(2) 0.056(2) 1.000 Uani . . C(20) 0.1833(3) 0.1673(4) -0.1381(1) 0.047(1) 1.000 Uani . . C(21) 0.0278(4) 0.2798(5) 0.0257(2) 0.076(2) 1.000 Uani . . C(22) 0.0571(4) 0.3558(6) 0.0835(2) 0.092(3) 1.000 Uani . . H(1) 0.69384 -0.09449 0.45822 0.06350 1.000 Uiso . . H(2) 0.53309 -0.05679 0.44824 0.06350 1.000 Uiso . . H(3) 0.68365 0.49258 0.50093 0.06138 1.000 Uiso . . H(4) 0.65892 0.65993 0.40586 0.07407 1.000 Uiso . . H(5) 0.62633 0.68754 0.31442 0.08541 1.000 Uiso . . H(6) 0.60561 0.49825 0.24647 0.08050 1.000 Uiso . . H(7) 0.60356 0.23420 0.25538 0.07329 1.000 Uiso . . H(8) 0.61467 0.08154 0.33301 0.06160 1.000 Uiso . . H(9) 0.76182 0.32986 0.58781 0.08025 1.000 Uiso . . H(10) 0.61373 0.33587 0.58848 0.08025 1.000 Uiso . . H(11) 0.63415 0.10321 0.64405 0.10857 1.000 Uiso . . H(12) 0.78238 0.09819 0.64360 0.10857 1.000 Uiso . . H(13) 0.72518 0.23935 0.67439 0.10857 1.000 Uiso . . H(14) 0.40988 0.21889 -0.06496 0.06756 1.000 Uiso . . H(15) 0.35117 0.34335 -0.02805 0.06756 1.000 Uiso . . H(16) -0.06953 0.13601 -0.08287 0.07379 1.000 Uiso . . H(17) -0.11396 0.00373 -0.18410 0.09466 1.000 Uiso . . H(18) -0.06274 -0.06880 -0.26391 0.10084 1.000 Uiso . . H(19) 0.12138 -0.03192 -0.29544 0.09570 1.000 Uiso . . H(20) 0.30140 0.08346 -0.25209 0.08413 1.000 Uiso . . H(21) 0.34716 0.19965 -0.16657 0.06666 1.000 Uiso . . H(22) -0.04344 0.33465 0.00370 0.09127 1.000 Uiso . . H(23) 0.00770 0.16792 0.02974 0.09127 1.000 Uiso . . H(24) 0.12909 0.30110 0.10621 0.11093 1.000 Uiso . . H(25) 0.07741 0.46767 0.08020 0.11093 1.000 Uiso . . H(26) -0.01726 0.34524 0.10058 0.11093 1.000 Uiso . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 N(1) 0.044(1) 0.036(1) 0.046(1) 0.001(1) 0.008(1) -0.010(1) N(2) 0.057(1) 0.034(1) 0.055(1) 0.001(1) 0.008(1) -0.008(1) N(3) 0.058(1) 0.052(1) 0.041(1) -0.002(1) 0.011(1) -0.012(1) N(4) 0.034(1) 0.050(1) 0.059(1) -0.004(1) 0.013(1) 0.003(1) N(5) 0.032(1) 0.067(2) 0.071(2) -0.007(1) 0.016(1) -0.010(1) N(6) 0.047(1) 0.059(2) 0.063(2) -0.003(1) 0.020(1) 0.003(1) C(1) 0.035(1) 0.046(2) 0.050(2) 0.002(1) 0.008(1) -0.015(1) C(2) 0.051(2) 0.044(2) 0.057(2) -0.005(1) 0.010(1) -0.013(1) C(3) 0.038(1) 0.042(2) 0.062(2) 0.001(1) 0.012(1) -0.004(1) C(4) 0.062(2) 0.043(2) 0.083(3) -0.001(1) 0.018(2) -0.004(2) C(5) 0.069(2) 0.066(3) 0.079(3) 0.007(2) 0.021(2) 0.018(2) C(6) 0.060(2) 0.078(3) 0.063(2) 0.005(2) 0.013(2) 0.015(2) C(7) 0.055(2) 0.081(3) 0.050(2) 0.003(2) 0.012(1) -0.003(2) C(8) 0.045(2) 0.053(2) 0.054(2) -0.001(1) 0.009(1) -0.007(1) C(9) 0.033(1) 0.047(2) 0.048(2) 0.005(1) 0.007(1) -0.007(1) C(10) 0.073(2) 0.069(2) 0.057(2) -0.005(2) 0.009(2) -0.022(2) C(11) 0.113(3) 0.104(3) 0.048(2) -0.021(3) 0.016(2) -0.013(2) C(12) 0.041(2) 0.046(2) 0.062(2) 0.000(1) 0.014(1) 0.009(1) C(13) 0.035(2) 0.068(2) 0.076(2) -0.006(1) 0.015(1) 0.007(2) C(14) 0.037(1) 0.058(2) 0.067(2) -0.002(1) 0.004(1) 0.009(2) C(15) 0.048(2) 0.092(3) 0.087(3) -0.012(2) -0.001(2) -0.001(2) C(16) 0.073(3) 0.090(3) 0.080(3) -0.011(2) -0.003(2) -0.006(2) C(17) 0.091(3) 0.076(3) 0.064(2) 0.002(2) 0.006(2) -0.005(2) C(18) 0.079(3) 0.068(2) 0.063(2) -0.003(2) 0.022(2) 0.001(2) C(19) 0.050(2) 0.056(2) 0.063(2) -0.003(1) 0.015(1) 0.001(2) C(20) 0.043(2) 0.042(2) 0.054(2) 0.003(1) 0.006(1) 0.007(1) C(21) 0.067(2) 0.091(3) 0.077(2) -0.006(2) 0.038(2) 0.006(2) C(22) 0.079(3) 0.123(4) 0.081(3) 0.013(2) 0.036(2) 0.006(3) #----------------------------------------------------------------------------- _refine_special_details ? _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme ' w = 1/[\s^2^(Fo) + 0.000225|Fo|^2^]' _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method Zachariasen_type_2_Gaussian_isotropic _refine_ls_extinction_coef 0.00000 _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 2206 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_number_constraints ?_ _refine_ls_R_factor_all ? _refine_ls_R_factor_obs 0.0629 _refine_ls_wR_factor_all ? _refine_ls_wR_factor_obs 0.0639 _refine_ls_goodness_of_fit_all ? _refine_ls_goodness_of_fit_obs 1.820 _refine_ls_shift/esd_max 0.0631 _refine_ls_shift/esd_mean ? _refine_diff_density_min -0.41 _refine_diff_density_max 0.29 #----------------------------------------------------------------------------- _geom_special_details ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag N(1) N(2) 1.407(4). . yes N(1) C(1) 1.407(4). . yes N(1) C(9) 1.365(4). . yes N(2) H(1) 1.020. . yes N(2) H(2) 1.119. . yes N(3) C(1) 1.283(4). . yes N(3) C(10) 1.470(4). . yes N(4) N(5) 1.402(4). . yes N(4) C(12) 1.409(4). . yes N(4) C(20) 1.365(4). . yes N(5) H(14) 0.966. . yes N(5) H(15) 0.970. . yes N(6) C(12) 1.284(4). . yes N(6) C(21) 1.466(4). . yes C(1) C(2) 1.441(5). . yes C(2) C(3) 1.363(4) . . yes C(2) H(3) 0.953. . yes C(3) C(4) 1.415(5). . yes C(3) C(9) 1.468(5). . yes C(4) C(5) 1.357(5). . yes C(4) H(4) 0.951. . yes C(5) C(6) 1.414(6). . yes C(5) H(5) 0.943. . yes C(6) C(7) 1.363(6). . yes C(6) H(6) 0.949 C(7) C(8) 1.414(5). . yes C(7) H(7) 0.951 . . yes C(8) C(9) 1.371(4). . yes C(8) H(8) 0.948 . . yes C(10) C(11) 1.491(5). . yes C(10) H(9) 0.948 . . yes C(10) H(10) 0.953. . yes C(11) H(11) 0.944. . yes C(11) H(12) 0.951. . yes C(11) H(13) 0.953. . yes C(12) C(13) 1.439(5). . yes C(13) C(14) 1.356(5). . yes C(13) H(16) 0.945 . . yes C(14) C(15) 1.427(5) . . yes C(14) C(20) 1.461(4) . . yes C(15) C(16) 1.358(6). . yes C(15) H(17) 0.953 . . yes C(16) C(17) 1.405(6). . yes C(16) H(18) 0.951. . yes C(17) C(18) 1.354(6) . . yes C(17) H(19) 0.955. . yes C(18) C(19) 1.405(5). . yes C(18) H(20) 0.950. . yes C(19) C(20) 1.369(5) . . yes C(19) H(21) 0.952. . yes C(21) C(22) 1.497(6). . yes C(21) H(22) 0.939. . yes C(21) H(23) 0.948. . yes C(22) H(24) 0.952. . yes C(22) H(25) 0.946. . yes C(22) H(26) 0.949. . yes #----------------------------------------------------------------------------- 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N(2) N(1) C(1) 124.9(3) . . . yes N(2) N(1) C(9) 122.3(3) . . . yes C(1) N(1) C(9) 112.6(3) . . . yes N(1) N(2) H(1) 117.17 . . . yes N(1) N(2) H(2) 109.12 . . . yes H(1) N(2) H(2) 103.26 . . . yes C(1) N(3) C(10) 115.2(3) . . . yes N(5) N(4) C(12) 124.3(3) . . . yes N(5) N(4) C(20) 122.8(3) . . . yes C(12) N(4) C(20) 112.9(3) . . . yes N(4) N(5) H(14) 109.81 . . . yes N(4) N(5) H(15) 109.69 . . . yes H(14) N(5) H(15) 106.52 . . . yes C(12) N(6) C(21) 115.6(3) . . . yes N(1) C(1) N(3) 121.6(3) . . . yes N(1) C(1) C(2) 104.0(3) . . . yes N(3) C(1) C(2) 134.4(3) . . . yes C(1) C(2) C(3) 110.3(3) . . . yes C(1) C(2) H(3) 124.66 . . . yes C(3) C(2) H(3) 125.07 . . . yes C(2) C(3) C(4) 127.3(3) . . . yes C(2) C(3) C(9) 107.6(3) . . . yes C(4) C(3) C(9) 125.1(3) . . . yes C(3) C(4) C(5) 129.4(4) . . . yes C(3) C(4) H(4) 115.97 . . . yes C(5) C(4) H(4) 114.65 . . . yes C(4) C(5) C(6) 130.0(4) . . . yes C(4) C(5) H(5) 115.97 . . . yes C(6) C(5) H(5) 113.98 . . . yes C(5) C(6) C(7) 127.9(4) . . . yes C(5) C(6) H(6) 117.06 . . . yes C(7) C(6) H(6) 115.00 . . . yes C(6) C(7) C(8) 130.2(4) . . . yes C(6) C(7) H(7) 115.32 . . . yes C(8) C(7) H(7) 114.44 . . . yes C(7) C(8) C(9) 126.9(3) . . . yes C(7) C(8) H(8) 116.29 . . . yes C(9) C(8) H(8) 116.79 . . . yes N(1) C(9) C(3) 105.5(3) . . . yes N(1) C(9) C(8) 124.2(3) . . . yes C(3) C(9) C(8) 130.3(3) . . . yes N(3) C(10) C(11) 111.5(3) . . . yes N(3) C(10) H(9) 108.19 . . . yes N(3) C(10) H(10) 108.07 . . . yes C(11) C(10) H(9) 110.15 . . . yes C(11) C(10) H(10) 109.55 . . . yes H(9) C(10) H(10) 109.36 . . . yes C(10) C(11) H(11) 109.89 . . . yes C(10) C(11) H(12) 109.24 . . . yes C(10) C(11) H(13) 108.88 . . . yes H(11) C(11) H(12) 109.90 . . . yes H(11) C(11) H(13) 109.77 . . . yes H(12) C(11) H(13) 109.15 . . . yes N(4) C(12) N(6) 121.0(3) . . . yes N(4) C(12) C(13) 103.3(3) . . . yes N(6) C(12) C(13) 135.7(3) . . . yes C(12) C(13) C(14) 110.8(3) . . . yes C(12) C(13) H(16) 124.87 . . . yes C(14) C(13) H(16) 124.33 . . . yes C(13) C(14) C(15) 127.8(4) . . . yes C(13) C(14) C(20) 107.7(3) . . . yes C(15) C(14) C(20) 124.4(4) . . . yes C(14) C(15) C(16) 129.5(4) . . . yes C(14) C(15) H(17) 115.04 . . . yes C(16) C(15) H(17) 115.46 . . . yes C(15) C(16) C(17) 130.0(4) . . . yes C(15) C(16) H(18) 114.92 . . . yes C(17) C(16) H(18) 115.12 . . . yes C(16) C(17) C(18) 128.3(4) . . . yes C(16) C(17) H(19) 115.48 . . . yes C(18) C(17) H(19) 116.18 . . . yes C(17) C(18) C(19) 129.7(4) . . . yes C(17) C(18) H(20) 115.24 . . . yes C(19) C(18) H(20) 115.02 . . . yes C(18) C(19) C(20) 127.9(3) . . . yes C(18) C(19) H(21) 116.28 . . . yes C(20) C(19) H(21) 115.85 . . . yes N(4) C(20) C(14) 105.3(3) . . . yes N(4) C(20) C(19) 124.5(3) . . . yes C(14) C(20) C(19) 130.1(3) . . . yes N(6) C(21) C(22) 111.8(3) . . . yes N(6) C(21) H(22) 108.94 . . . yes N(6) C(21) H(23) 108.52 . . . yes C(22) C(21) H(22) 108.64 . . . yes C(22) C(21) H(23) 108.35 . . . yes H(22) C(21) H(23) 110.56 . . . yes C(21) C(22) H(24) 109.45 . . . yes C(21) C(22) H(25) 109.46 . . . yes C(21) C(22) H(26) 108.97 . . . yes H(24) C(22) H(25) 109.69 . . . yes H(24) C(22) H(26) 109.39 . . . yes H(25) C(22) H(26) 109.87 . . . yes #----------------------------------------------------------------------------- _publ_contact_author_name 'Prof. Noritaka Abe' _publ_contact_author_address ; Department of Chemistry, Faculty of Science, Yamaguchi University, Yamaguchi 753-8512, Japan ; _publ_contact_letter ; ENTER TEXT OF LETTER ; _publ_requested_journal 'J. Chem. Soc., Perkin 1' _publ_requested_coeditor_name ? _publ_contact_author_phone '+81-839-33-5732' _publ_contact_author_fax '+81-839-33-5732' _publ_contact_author_email 'abe@po.cc.yamaguchi-u.ac.jp' _publ_section_title ; ENTER SECTION TITLE ; loop_ _publ_author_name _publ_author_address 'Noritaka Abe' ; Department of Chemistry, Faculty of Science, Yamaguchi University, Yamaguchi 753-8512, Japan ; _publ_section_abstract ; ENTER ABSTRACT ; _publ_section_experimental ; ENTER EXPERIMENTAL SECTION ; _publ_section_comment ; ENTER TEXT ; _publ_section_references ; Burla, M. C., Camalli, M., Cascarano, G., Giacovazzo, C., Polidoli, G., Spag na, R., and Viterbo, D., J. Appl. Cryst. 22, 389-393 (1989). Johnson, C. K., ORTEP. Report ORNL-3794. Oak Ridge National Laboratory, Tennessee, USA (1965). TEXSAN: Single Crystal Structure Analysis Software, Version 2.0, (1989). Molecular Structure Corporation, The Woodlands, TX. 77381. ; _publ_section_acknowledgements ; ENTER ACKNOWLEDGEMENTS ; _publ_section_table_legends ; ENTER TABLE LEGENDS ; _publ_section_figure_captions ; ENTER FIGURE CAPTIONS ; data_triazabenz[cd]azulene #----------------------------------------------------------------------------- _audit_creation_date ' 8-NOV-97 09:00:23' _audit_creation_method 'from TEXRAY.INF file' _audit_update_record ? #----------------------------------------------------------------------------- _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'TEXSAN' _computing_structure_solution 'SIR (Burla et al.,1989)' _computing_structure_refinement 'TEXSAN' _computing_publication_material 'TEXSAN' _computing_molecular_graphics 'ORTEP (Johnson, 1965)' #----------------------------------------------------------------------------- _chemical_name_common ? _chemical_formula_weight 342.35 _chemical_formula_analytical ? _chemical_formula_sum 'C17 H18 N4 O4 ' _chemical_formula_moiety 'C17 H18 N4 O4 ' _chemical_formula_structural ? _chemical_melting_point ? #----------------------------------------------------------------------------- _cell_length_a 7.546(7) _cell_length_b 9.524(5) _cell_length_c 22.971(5) _cell_angle_alpha 90 _cell_angle_beta 92.22(3) _cell_angle_gamma 90 _cell_volume 1650(1) _cell_formula_units_Z 4 _cell_measurement_temperature 296.2 _cell_measurement_reflns_used 24 _cell_measurement_theta_min 18.9 _cell_measurement_theta_max 19.9 #----------------------------------------------------------------------------- _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/N ' _symmetry_Int_Tables_number 14 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' '1/2-x,1/2+y,1/2-z' ' -x, -y, -z' '1/2+x,1/2+y,1/2+z' #----------------------------------------------------------------------------- _exptl_crystal_description 'prism' _exptl_crystal_colour 'black' _exptl_crystal_size_max 0.240 _exptl_crystal_size_mid 0.420 _exptl_crystal_size_min 0.640 _exptl_crystal_density_diffrn 1.378 _exptl_crystal_density_meas 'not measured' _exptl_crystal_F_000 720.00 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type 'none' _exptl_special_details ? #----------------------------------------------------------------------------- _diffrn_special_details ? _diffrn_ambient_temperature 296.2 _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device 'Rigaku AFC5S' _diffrn_measurement_method \w-2\q _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% -0.60 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 3 -1 2 2 0 0 2 0 6 _diffrn_reflns_number 4315 _reflns_number_total 4315 _reflns_number_observed 1817 _reflns_observed_criterion >2.0sigma(I) _diffrn_reflns_av_R_equivalents 0.00 _diffrn_reflns_av_sigmaI/netI 0.000 _diffrn_reflns_limit_h_min ? _diffrn_reflns_limit_h_max ? _diffrn_reflns_limit_k_min ? _diffrn_reflns_limit_k_max ? _diffrn_reflns_limit_l_min ? _diffrn_reflns_limit_l_max ? _diffrn_reflns_theta_min 0.00 _diffrn_reflns_theta_max 0.00 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 0.06032 _diffrn_orient_matrix_UB_12 -0.08147 _diffrn_orient_matrix_UB_13 0.01980 _diffrn_orient_matrix_UB_21 0.04385 _diffrn_orient_matrix_UB_22 -0.03240 _diffrn_orient_matrix_UB_23 -0.03827 _diffrn_orient_matrix_UB_31 0.10966 _diffrn_orient_matrix_UB_32 0.05777 _diffrn_orient_matrix_UB_33 0.00646 #----------------------------------------------------------------------------- loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 68 0.002 0.002 'International Tables Vol IV Table 2.2A' H 0 72 0.000 0.000 'International Tables Vol IV Table 2.2A' N 0 16 0.004 0.003 'International Tables Vol IV Table 2.2A' O 0 16 0.008 0.006 'International Tables Vol IV Table 2.2A' #----------------------------------------------------------------------------- loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom O(1) 0.4344(7) 0.0642(5) 0.2977(2) 0.084(3) 1.000 Uani . . O(2) 0.5043(7) 0.1615(5) 0.2131(2) 0.082(3) 1.000 Uani . . O(3) 0.4272(6) -0.1661(5) 0.1878(2) 0.071(3) 1.000 Uani . . O(4) 0.3699(6) -0.2733(4) 0.1037(2) 0.062(2) 1.000 Uani . . N(1) 0.1365(6) 0.1864(5) 0.1367(2) 0.044(3) 1.000 Uani . . N(2) 0.1286(6) 0.2081(5) 0.0772(2) 0.039(2) 1.000 Uani . . N(3) 0.0717(6) 0.3184(5) -0.0059(2) 0.046(3) 1.000 Uani . . N(4) -0.0025(8) 0.4334(5) 0.0821(2) 0.064(3) 1.000 Uani . . C(1) 0.0633(8) 0.3271(6) 0.0513(2) 0.043(3) 1.000 Uani . . C(2) 0.2152(7) 0.0688(6) 0.1516(2) 0.040(3) 1.000 Uani . . C(3) 0.2767(8) -0.0378(6) 0.1123(2) 0.041(3) 1.000 Uani . . C(4) 0.2555(7) -0.0129(6) 0.0510(2) 0.039(3) 1.000 Uani . . C(5) 0.3113(8) -0.1077(6) 0.0057(3) 0.051(3) 1.000 Uani . . C(6) 0.3048(8) -0.0902(6) -0.0536(3) 0.055(4) 1.000 Uani . . C(7) 0.242(1) 0.0213(7) -0.0905(3) 0.060(4) 1.000 Uani . . C(8) 0.1723(8) 0.1443(6) -0.0753(3) 0.048(3) 1.000 Uani . . C(9) 0.1427(7) 0.1882(6) -0.0177(2) 0.039(3) 1.000 Uani . . C(10) 0.1794(7) 0.1158(6) 0.0342(2) 0.039(3) 1.000 Uani . . C(11) 0.2249(9) 0.0545(6) 0.2174(3) 0.052(3) 1.000 Uani . . C(12) 0.3979(9) 0.0906(7) 0.2476(3) 0.056(4) 1.000 Uani . . C(13) 0.671(1) 0.212(1) 0.2388(4) 0.113(7) 1.000 Uani . . C(14) 0.722(1) 0.323(1) 0.2183(8) 0.22(1) 1.000 Uani . . C(15) 0.3623(8) -0.1628(6) 0.1384(3) 0.044(3) 1.000 Uani . . C(16) 0.457(1) -0.3980(8) 0.1272(3) 0.073(4) 1.000 Uani . . C(17) 0.490(1) -0.4911(9) 0.0777(4) 0.099(6) 1.000 Uani . . H(1) -0.03771 0.52577 0.06013 0.07063 1.000 Uiso . . H(2) 0.00790 0.44270 0.11727 0.07063 1.000 Uiso . . H(3) 0.36068 -0.19668 0.01908 0.06406 1.000 Uiso . . H(4) 0.35479 -0.16737 -0.07456 0.06699 1.000 Uiso . . H(5) 0.25242 0.00616 -0.13153 0.07364 1.000 Uiso . . H(6) 0.12934 0.20669 -0.10628 0.05975 1.000 Uiso . . H(7) 0.13337 0.11488 0.23253 0.06416 1.000 Uiso . . H(8) 0.19303 -0.04017 0.22663 0.06416 1.000 Uiso . . H(9) 0.67242 0.20099 0.28129 0.11843 1.000 Uiso . . H(10) 0.76859 0.15152 0.22646 0.11843 1.000 Uiso . . H(11) 0.81351 0.36130 0.24428 0.28433 1.000 Uiso . . H(12) 0.70734 0.33949 0.18579 0.28433 1.000 Uiso . . H(13) 0.61079 0.38897 0.24056 0.28433 1.000 Uiso . . H(14) 0.57205 -0.37312 0.14436 0.08296 1.000 Uiso . . H(15) 0.38977 -0.44105 0.15570 0.08296 1.000 Uiso . . H(16) 0.37060 -0.51820 0.06126 0.11368 1.000 Uiso . . H(17) 0.55362 -0.45113 0.05025 0.11368 1.000 Uiso . . H(18) 0.54063 -0.57782 0.09232 0.11368 1.000 Uiso . . #----------------------------------------------------------------------------- loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O(1) 0.101(4) 0.110(4) 0.038(2) 0.022(3) -0.015(2) 0.011(2) O(2) 0.097(4) 0.084(3) 0.063(3) -0.028(3) -0.033(2) 0.021(2) O(3) 0.105(3) 0.059(3) 0.046(2) 0.020(2) -0.023(2) 0.003(2) O(4) 0.085(3) 0.045(2) 0.055(2) 0.014(2) -0.009(2) -0.002(2) N(1) 0.050(3) 0.050(3) 0.033(2) 0.000(2) 0.003(2) 0.002(2) N(2) 0.039(2) 0.040(2) 0.038(2) 0.008(2) -0.001(2) 0.001(2) N(3) 0.055(3) 0.041(3) 0.041(3) 0.003(2) -0.004(2) 0.002(2) N(4) 0.112(4) 0.047(3) 0.033(3) 0.016(3) 0.002(2) -0.003(2) C(1) 0.050(3) 0.040(3) 0.039(3) 0.003(3) -0.004(2) 0.003(2) C(2) 0.038(3) 0.043(3) 0.039(3) -0.001(2) 0.000(2) 0.007(2) C(3) 0.049(3) 0.043(3) 0.032(3) 0.002(2) -0.004(2) 0.003(2) C(4) 0.036(3) 0.036(3) 0.043(3) -0.005(2) 0.001(2) -0.003(2) C(5) 0.063(4) 0.048(3) 0.043(3) -0.002(3) 0.000(3) -0.002(3) C(6) 0.067(4) 0.048(3) 0.049(4) 0.006(3) 0.003(3) -0.013(3) C(7) 0.088(5) 0.061(4) 0.032(3) -0.002(4) 0.004(3) -0.006(3) C(8) 0.059(4) 0.048(3) 0.037(3) -0.005(3) -0.002(2) 0.001(3) C(9) 0.032(3) 0.042(3) 0.044(3) -0.007(2) -0.002(2) 0.001(2) C(10) 0.038(3) 0.043(3) 0.034(3) -0.009(2) 0.001(2) -0.001(2) C(11) 0.065(4) 0.051(3) 0.039(3) 0.007(3) 0.007(3) 0.005(3) C(12) 0.070(4) 0.050(4) 0.047(4) 0.011(3) -0.011(3) 0.002(3) C(13) 0.117(7) 0.088(6) 0.128(8) -0.013(6) -0.077(6) 0.017(6) C(14) 0.18(1) 0.11(1) 0.36(2) -0.078(9) -0.18(1) 0.10(1) C(15) 0.040(3) 0.045(3) 0.048(3) -0.001(3) 0.001(2) 0.003(3) C(16) 0.098(5) 0.053(4) 0.067(4) 0.025(4) -0.010(4) 0.006(3) C(17) 0.141(8) 0.075(5) 0.081(6) 0.035(5) 0.000(5) -0.017(4) #----------------------------------------------------------------------------- _refine_special_details ? _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme ' w = 1/[\s^2^(Fo) + 0.000225|Fo|^2^]' _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method 'Zachariasen_type_2_Gaussian_isotropic' _refine_ls_extinction_coef 0.00000 _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1817 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_number_constraints ? _refine_ls_R_factor_all ? _refine_ls_R_factor_obs 0.0824 _refine_ls_wR_factor_all ? _refine_ls_wR_factor_obs 0.0994 _refine_ls_goodness_of_fit_all ? _refine_ls_goodness_of_fit_obs 2.841 _refine_ls_shift/esd_max 0.2486 _refine_ls_shift/esd_mean ? _refine_diff_density_min -0.36 _refine_diff_density_max 0.35 #----------------------------------------------------------------------------- _geom_special_details ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C12 1.200(7) . . yes O2 C12 1.333(8) . . yes O2 C13 1.451(9) . . yes O3 C15 1.218(6) . . yes O4 C15 1.322(7) . . yes O4 C16 1.451(7) . . yes N1 N2 1.382(6) . . yes N1 C2 1.308(7) . . yes N2 C1 1.364(7) . . yes N2 C10 1.387(7) . . yes N3 C1 1.319(7) . . yes N3 C9 1.382(7) . . yes N4 C1 1.342(7) . . yes N4 H1 1.043 . . yes N4 H2 0.814 . . yes C2 C3 1.447(8) . . yes C2 C11 1.516(8) . . yes C3 C4 1.431(7) . . yes C3 C15 1.471(8) . . yes C4 C5 1.452(8) . . yes C4 C10 1.401(8) . . yes C5 C6 1.372(8) . . yes C5 H3 0.971 . . yes C6 C7 1.427(9) . . yes C6 H4 0.964 . . yes C7 C8 1.337(8) . . yes C7 H5 0.960 . . yes C8 C9 1.415(8) . . yes C8 H6 0.973 . . yes C9 C10 1.396(7) . . yes C11 C12 1.495(9) . . yes C11 H7 0.973 . . yes C11 H8 0.959 . . yes C13 C14 1.23(1) . . yes C13 H9 0.982 . . yes C13 H10 0.985 . . yes C14 H11 0.965 . . yes C14 H12 0.766 . . yes C14 H13 1.178 . . yes C16 C17 1.47(1) . . yes C16 H14 0.968 . . yes C16 H15 0.940 . . yes C17 H16 0.995 . . yes C17 H17 0.895 . . yes C17 H18 0.966 . . yes #----------------------------------------------------------------------------- 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 O2 C13 117.4(6) . . . yes C15 O4 C16 117.2(5) . . . yes N2 N1 C2 112.9(5) . . . yes N1 N2 C1 123.9(5) . . . yes N1 N2 C10 127.3(5) . . . yes C1 N2 C10 108.8(5) . . . yes C1 N3 C9 106.6(5) . . . yes C1 N4 H1 118.28 . . . yes C1 N4 H2 125.63 . . . yes H1 N4 H2 113.67 . . . yes N2 C1 N3 110.6(5) . . . yes N2 C1 N4 122.1(5) . . . yes N3 C1 N4 127.3(5) . . . yes N1 C2 C3 126.2(5) . . . yes N1 C2 C11 110.0(5) . . . yes C3 C2 C11 123.7(5) . . . yes C2 C3 C4 118.2(5) . . . yes C2 C3 C15 117.4(5) . . . yes C4 C3 C15 124.4(5) . . . yes C3 C4 C5 125.3(5) . . . yes C3 C4 C10 116.4(5) . . . yes C5 C4 C10 118.3(5) . . . yes C4 C5 C6 129.5(6) . . . yes C4 C5 H3 115.79 . . . yes C6 C5 H3 114.70 . . . yes C5 C6 C7 132.7(6) . . . yes C5 C6 H4 113.85 . . . yes C7 C6 H4 113.41 . . . yes C6 C7 C8 128.5(6) . . . yes C6 C7 H5 115.78 . . . yes C8 C7 H5 115.77 . . . yes C7 C8 C9 125.6(6) . . . yes C7 C8 H6 117.95 . . . yes C9 C8 H6 116.32 . . . yes N3 C9 C8 121.7(5) . . . yes N3 C9 C10 110.0(5) . . . yes C8 C9 C10 128.3(5) . . . yes N2 C10 C4 118.7(5) . . . yes N2 C10 C9 104.1(5) . . . yes C4 C10 C9 137.1(5) . . . yes C2 C11 C12 116.7(5) . . . yes C2 C11 H7 107.18 . . . yes C2 C11 H8 107.53 . . . yes C12 C11 H7 108.54 . . . yes C12 C11 H8 109.63 . . . yes H7 C11 H8 106.77 . . . yes O1 C12 O2 123.7(6) . . . yes O1 C12 C11 124.1(7) . . . yes O2 C12 C11 112.1(5) . . . yes O2 C13 C14 114.2(9) . . . yes O2 C13 H9 110.06 . . . yes O2 C13 H10 109.59 . . . yes C14 C13 H9 118.83 . . . yes C14 C13 H10 98.50 . . . yes H9 C13 H10 104.14 . . . yes C13 C14 H11 108.22 . . . yes C13 C14 H12 120.68 . . . yes C13 C14 H13 93.04 . . . yes H11 C14 H12 126.94 . . . yes H11 C14 H13 92.20 . . . yes H12 C14 H13 103.85 . . . yes O3 C15 O4 121.0(6) . . . yes O3 C15 C3 123.7(6) . . . yes O4 C15 C3 115.3(5) . . . yes O4 C16 C17 107.1(6) . . . yes O4 C16 H14 109.75 . . . yes O4 C16 H15 111.47 . . . yes C17 C16 H14 106.83 . . . yes C17 C16 H15 112.73 . . . yes H14 C16 H15 108.82 . . . yes C16 C17 H16 105.99 . . . yes C16 C17 H17 113.51 . . . yes C16 C17 H18 108.90 . . . yes H16 C17 H17 110.28 . . . yes H16 C17 H18 104.61 . . . yes H17 C17 H18 112.95 . . . yes #----------------------------------------------------------------------------- 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 O1 C12 O2 C13 -2(1) . . . . yes O1 C12 C11 C2 -167.9(6) . . . . yes O2 C12 C11 C2 14.9(8) . . . . yes O3 C15 O4 C16 0.5(9) . . . . yes O3 C15 C3 C2 -20.9(9) . . . . yes O3 C15 C3 C4 157.1(6) . . . . yes O4 C15 C3 C2 161.2(5) . . . . yes O4 C15 C3 C4 -20.8(8) . . . . yes N1 N2 C1 N3 -179.7(5) . . . . yes N1 N2 C1 N4 -1.2(9) . . . . yes N1 N2 C10 C4 -3.1(8) . . . . yes N1 N2 C10 C9 179.4(5) . . . . yes N1 C2 C3 C4 1.9(9) . . . . yes N1 C2 C3 C15 -180.0(5) . . . . yes N1 C2 C11 C12 -100.3(6) . . . . yes N2 N1 C2 C3 -5.2(8) . . . . yes N2 N1 C2 C11 177.9(5) . . . . yes N2 C1 N3 C9 0.8(6) . . . . yes N2 C10 C4 C3 -0.8(7) . . . . yes N2 C10 C4 C5 -178.9(5) . . . . yes N2 C10 C9 N3 -0.3(6) . . . . yes N2 C10 C9 C8 178.6(5) . . . . yes N3 C1 N2 C10 -1.1(6) . . . . yes N3 C9 C8 C7 179.1(6) . . . . yes N3 C9 C10 C4 -177.0(6) . . . . yes N4 C1 N2 C10 177.4(5) . . . . yes N4 C1 N3 C9 -177.6(6) . . . . yes C1 N2 N1 C2 -175.6(5) . . . . yes C1 N2 C10 C4 178.3(5) . . . . yes C1 N2 C10 C9 0.8(6) . . . . yes C1 N3 C9 C8 -179.3(5) . . . . yes C1 N3 C9 C10 -0.3(6) . . . . yes C2 N1 N2 C10 6.0(7) . . . . yes C2 C3 C4 C5 179.3(5) . . . . yes C2 C3 C4 C10 1.4(7) . . . . yes C3 C2 C11 C12 82.7(7) . . . . yes C3 C4 C5 C6 -176.4(6) . . . . yes C3 C4 C10 C9 175.5(6) . . . . yes C3 C15 O4 C16 178.5(5) . . . . yes C4 C3 C2 C11 178.3(5) . . . . yes C4 C5 C6 C7 -1(1) . . . . yes C4 C10 C9 C8 2(1) . . . . yes C5 C4 C3 C15 1.3(9) . . . . yes C5 C4 C10 C9 -3(1) . . . . yes C5 C6 C7 C8 1(1) . . . . yes C6 C5 C4 C10 1.5(9) . . . . yes C6 C7 C8 C9 -1(1) . . . . yes C7 C8 C9 C10 0(1) . . . . yes C10 C4 C3 C15 -176.6(5) . . . . yes C11 C2 C3 C15 -3.5(8) . . . . yes C11 C12 O2 C13 175.4(6) . . . . yes C12 O2 C13 C14 -147(1) . . . . yes C15 O4 C16 C17 -165.8(6) . . . . yes #----------------------------------------------------------------------------- _publ_requested_journal 'J. Chem.Soc., Perkin 1' _publ_contact_author ; Noritaka Abe Department of Chemistry, Faculty of Science, Yamaguchi University, Yamaguchi 752-8512, Japan ; _publ_contact_letter ; ENTER TEXT OF LETTER ; _publ_requested_coeditor_name ? _publ_contact_author_phone ' +81-839-33-5732 ' _publ_contact_author_fax ' +81-839-33-5732 ' _publ_contact_author_email ' abe@po.cc.yamaguchi-u.ac.jp ' loop_ _publ_author_name _publ_author_address ' Noritaka Abe ' ; Department of Chemistry, Faculty of Science, Yamaguchi University, Yamaguchi 752-8512, Japan ; _publ_section_title ; ENTER SECTION TITLE ; _publ_section_abstract ; ENTER ABSTRACT ; _publ_section_experimental ; ENTER EXPERIMENTAL SECTION ; _publ_section_comment ; ENTER TEXT ; _publ_section_references ; Burla, M. C., Camalli, M., Cascarano, G., Giacovazzo, C., Polidoli, G., Spagna, R., & Viterbo, D., J. Appl. Cryst. 22, 389-393 (1989). Johnson, C. K., ORTEP. Report ORNL-3794. Oak Ridge National Laboratory, Tennessee, USA (1965). TEXSAN: Single Crystal Structure Analysis Software, Version 2.0, (1989). Molecular Structure Corporation, The Woodlands, TX. 77381. ; _publ_section_acknowledgements ; ENTER ACKNOWLEDGEMENTS ; _publ_section_table_legends ; ENTER TABLE LEGENDS ; _publ_section_figure_captions ; ENTER FIGURE CAPTIONS ; data_tetraazacyclopent[a]azulene #----------------------------------------------------------------------------- _audit_creation_date ' 8-NOV-97 08:58:59' _audit_creation_method 'from TEXRAY.INF file' _audit_update_record ? #----------------------------------------------------------------------------- _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'TEXSAN' _computing_structure_solution 'MITHRIL (Gilmore, 1984)' _computing_structure_refinement 'TEXSAN' _computing_publication_material 'TEXSAN' _computing_molecular_graphics 'ORTEP (Johnson, 1965)' #----------------------------------------------------------------------------- _chemical_name_common ? _chemical_formula_weight 170.17 _chemical_formula_analytical ? _chemical_formula_sum 'C9 H6 N4 ' _chemical_formula_moiety 'C9 H6 N4 ' _chemical_formula_structural ? _chemical_melting_point 202 #----------------------------------------------------------------------------- _cell_length_a 3.825(9) _cell_length_b 12.928(4) _cell_length_c 15.603(5) _cell_angle_alpha 90 _cell_angle_beta 93.58(7) _cell_angle_gamma 90 _cell_volume 770(1) _cell_formula_units_Z 4 _cell_measurement_temperature 296 _cell_measurement_reflns_used 24 _cell_measurement_theta_min 19.1 _cell_measurement_theta_max 19.7 #----------------------------------------------------------------------------- _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/N ' _symmetry_Int_Tables_number 14 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' '1/2-x,1/2+y,1/2-z' ' -x, -y, -z' '1/2+x,1/2+y,1/2+z' #----------------------------------------------------------------------------- _exptl_crystal_description 'prism' _exptl_crystal_colour 'orange' _exptl_crystal_size_max 0.100 _exptl_crystal_size_mid 0.240 _exptl_crystal_size_min 0.660 _exptl_crystal_density_diffrn 1.468 _exptl_crystal_density_meas 'not measured' _exptl_crystal_F_000 352.00 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type 'none' _exptl_special_details ? #----------------------------------------------------------------------------- _diffrn_special_details ? _diffrn_ambient_temperature 296.2 _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device 'Rigaku AFC5S' _diffrn_measurement_method \w-2\q _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% 1.06 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -1 1 -3 -1 0 -3 -1 -2 -1 _diffrn_reflns_number 2107 _reflns_number_total 2107 _reflns_number_observed 1118 _reflns_observed_criterion >2.0sigma(I) _diffrn_reflns_av_R_equivalents 0.00 _diffrn_reflns_av_sigmaI/netI 0.000 _diffrn_reflns_limit_h_min ? _diffrn_reflns_limit_h_max ? _diffrn_reflns_limit_k_min ? _diffrn_reflns_limit_k_max ? _diffrn_reflns_limit_l_min ? _diffrn_reflns_limit_l_max ? _diffrn_reflns_theta_min 0.00 _diffrn_reflns_theta_max 0.00 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 -0.00286 _diffrn_orient_matrix_UB_12 -0.01843 _diffrn_orient_matrix_UB_13 -0.06228 _diffrn_orient_matrix_UB_21 0.01198 _diffrn_orient_matrix_UB_22 -0.07505 _diffrn_orient_matrix_UB_23 0.01541 _diffrn_orient_matrix_UB_31 -0.26168 _diffrn_orient_matrix_UB_32 -0.00323 _diffrn_orient_matrix_UB_33 -0.00263 #----------------------------------------------------------------------------- loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 36 0.002 0.002 'International Tables Vol IV Table 2.2A' H 0 24 0.000 0.000 'International Tables Vol IV Table 2.2A' N 0 16 0.004 0.003 'International Tables Vol IV Table 2.2A' #----------------------------------------------------------------------------- loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom N(1) 0.3822(5) 0.0381(2) 0.2683(1) 0.057(1) 1.000 Uani . . N(2) 0.1855(5) -0.0076(1) 0.1311(1) 0.049(1) 1.000 Uani . . N(3) 0.3358(4) 0.0882(1) 0.1335(1) 0.0368(9) 1.000 Uani . . N(4) 0.6029(5) 0.2092(2) 0.2180(1) 0.050(1) 1.000 Uani . . C(1) 0.2231(7) -0.0314(2) 0.2135(2) 0.057(1) 1.000 Uani . . C(2) 0.4117(5) 0.1653(2) 0.0775(1) 0.034(1) 1.000 Uani . . C(3) 0.3386(5) 0.1648(2) -0.0089(1) 0.043(1) 1.000 Uani . . C(4) 0.4136(7) 0.2440(2) -0.0664(2) 0.058(1) 1.000 Uani . . C(5) 0.5714(7) 0.3374(2) -0.0487(2) 0.066(1) 1.000 Uani . . C(6) 0.7006(7) 0.3782(2) 0.0303(2) 0.063(1) 1.000 Uani . . C(7) 0.7068(6) 0.3378(2) 0.1107(2) 0.053(1) 1.000 Uani . . C(8) 0.5826(5) 0.2418(2) 0.1357(1) 0.040(1) 1.000 Uani . . C(9) 0.4506(6) 0.1142(2) 0.2148(1) 0.044(1) 1.000 Uani . . H(1) 0.155(6) -0.099(1) 0.234(1) 0.066(7) 1.000 Uiso . . H(2) 0.226(5) 0.104(1) -0.032(1) 0.048(6) 1.000 Uiso . . H(3) 0.349(6) 0.231(1) -0.125(1) 0.065(7) 1.000 Uiso . . H(4) 0.593(6) 0.387(2) -0.096(1) 0.081(8) 1.000 Uiso . . H(5) 0.800(6) 0.447(1) 0.028(1) 0.075(7) 1.000 Uiso . . H(6) 0.808(6) 0.380(1) 0.159(1) 0.079(8) 1.000 Uiso . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 N(1) 0.063(1) 0.066(1) 0.042(1) 0.010(1) 0.0050(9) 0.011(1) N(2) 0.051(1) 0.039(1) 0.057(1) -0.0076(9) 0.0045(9) 0.0011(9) N(3) 0.036(1) 0.037(1) 0.037(1) 0.0000(8) -0.0002(7) -0.0034(8) N(4) 0.049(1) 0.056(1) 0.044(1) 0.000(1) -0.0080(8) -0.0125(9) C(1) 0.059(1) 0.052(1) 0.062(1) 0.003(1) 0.012(1) 0.018(1) C(2) 0.030(1) 0.035(1) 0.037(1) 0.0025(9) 0.0019(8) -0.0016(9) C(3) 0.042(1) 0.048(1) 0.040(1) 0.002(1) -0.0006(9) -0.006(1) C(4) 0.060(1) 0.071(1) 0.042(1) 0.014(1) 0.008(1) 0.013(1) C(5) 0.063(1) 0.058(1) 0.079(2) 0.016(1) 0.027(1) 0.028(1) C(6) 0.047(1) 0.040(1) 0.104(2) -0.002(1) 0.022(1) 0.009(1) C(7) 0.039(1) 0.041(1) 0.078(1) -0.005(1) 0.005(1) -0.012(1) C(8) 0.030(1) 0.041(1) 0.049(1) 0.0034(9) -0.0008(9) -0.009(1) C(9) 0.041(1) 0.052(1) 0.038(1) 0.008(1) -0.0018(9) -0.006(1) #----------------------------------------------------------------------------- _refine_special_details ? _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme ' w = 1/[\s^2^(Fo) + 0.000225|Fo|^2^]' _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method 'Zachariasen_type_2_Gaussian_isotropic' _refine_ls_extinction_coef 0.01189 _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1118 _refine_ls_number_parameters 143 _refine_ls_number_restraints 0 _refine_ls_number_constraints ? _refine_ls_R_factor_all ? _refine_ls_R_factor_obs 0.0431 _refine_ls_wR_factor_all ? _refine_ls_wR_factor_obs 0.0479 _refine_ls_goodness_of_fit_all ? _refine_ls_goodness_of_fit_obs 1.441 _refine_ls_shift/esd_max 0.0017 _refine_ls_shift/esd_mean ? _refine_diff_density_min -0.16 _refine_diff_density_max 0.16 #----------------------------------------------------------------------------- _geom_special_details ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.358(3) . . yes N1 C9 1.327(3) . . yes N2 N3 1.366(2) . . yes N2 C1 1.320(3) . . yes N3 C2 1.369(2) . . yes N3 C9 1.358(3) . . yes N4 C8 1.349(3) . . yes N4 C9 1.359(3) . . yes C1 H1 0.97(2) . . yes C2 C3 1.360(3) . . yes C2 C8 1.468(3) . . yes C3 C4 1.403(3) . . yes C3 H2 0.95(2) . . yes C4 C5 1.371(4) . . yes C4 H3 0.95(2) . . yes C5 C6 1.401(4) . . yes C5 H4 0.99(2) . . yes C6 C7 1.357(4) . . yes C6 H5 0.97(2) . . yes C7 C8 1.394(3) . . yes C7 H6 1.00(2) . . yes #----------------------------------------------------------------------------- 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C9 101.0(2) . . . yes N3 N2 C1 99.4(2) . . . yes N2 N3 C2 138.5(2) . . . yes N2 N3 C9 111.1(2) . . . yes C2 N3 C9 110.4(2) . . . yes C8 N4 C9 104.4(2) . . . yes N1 C1 N2 118.5(2) . . . yes N1 C1 H1 120(1) . . . yes N2 C1 H1 121(1) . . . yes N3 C2 C3 126.2(2) . . . yes N3 C2 C8 101.5(2) . . . yes C3 C2 C8 132.3(2) . . . yes C2 C3 C4 126.3(2) . . . yes C2 C3 H2 116(1) . . . yes C4 C3 H2 118(1) . . . yes C3 C4 C5 128.3(3) . . . yes C3 C4 H3 116(1) . . . yes C5 C4 H3 116(1) . . . yes C4 C5 C6 129.4(3) . . . yes C4 C5 H4 118(2) . . . yes C6 C5 H4 112(2) . . . yes C5 C6 C7 130.8(2) . . . yes C5 C6 H5 116(1) . . . yes C7 C6 H5 113(1) . . . yes C6 C7 C8 127.9(2) . . . yes C6 C7 H6 118(1) . . . yes C8 C7 H6 114(1) . . . yes N4 C8 C2 112.0(2) . . . yes N4 C8 C7 123.0(2) . . . yes C2 C8 C7 124.9(2) . . . yes N1 C9 N3 109.9(2) . . . yes N1 C9 N4 138.4(2) . . . yes N3 C9 N4 111.7(2) . . . yes #----------------------------------------------------------------------------- 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 N1 C1 N2 N3 -0.3(3) . . . . yes N1 C9 N3 N2 0.0(2) . . . . yes N1 C9 N3 C2 -178.7(2) . . . . yes N1 C9 N4 C8 178.9(3) . . . . yes N2 N3 C2 C3 0.9(4) . . . . yes N2 N3 C2 C8 -179.0(2) . . . . yes N2 N3 C9 N4 179.6(2) . . . . yes N2 C1 N1 C9 0.4(3) . . . . yes N3 C2 C3 C4 179.4(2) . . . . yes N3 C2 C8 N4 0.5(2) . . . . yes N3 C2 C8 C7 -178.7(2) . . . . yes N3 C9 N1 C1 -0.2(2) . . . . yes N3 C9 N4 C8 -0.5(2) . . . . yes N4 C8 C2 C3 -179.4(2) . . . . yes N4 C8 C7 C6 179.8(2) . . . . yes N4 C9 N1 C1 -179.6(3) . . . . yes N4 C9 N3 C2 0.9(2) . . . . yes C1 N2 N3 C2 178.4(2) . . . . yes C1 N2 N3 C9 0.2(2) . . . . yes C2 C3 C4 C5 -0.4(4) . . . . yes C2 C8 N4 C9 -0.1(2) . . . . yes C2 C8 C7 C6 -1.0(4) . . . . yes C3 C2 N3 C9 179.1(2) . . . . yes C3 C2 C8 C7 1.4(3) . . . . yes C3 C4 C5 C6 0.5(5) . . . . yes C4 C3 C2 C8 -0.6(4) . . . . yes C4 C5 C6 C7 0.0(5) . . . . yes C5 C6 C7 C8 0.3(4) . . . . yes C7 C8 N4 C9 179.2(2) . . . . yes C8 C2 N3 C9 -0.8(2) . . . . yes #----------------------------------------------------------------------------- _publ_requested_journal 'J. Chem. Soc. Perkin.1' _publ_contact_author ; Noritaka Abe Dpartment of Chemistry, Faculty of Science, Yamaguchi University, Yamaguc hi 752-8512, Japan ; _publ_contact_letter ; ENTER TEXT OF LETTER ; _publ_requested_coeditor_name ? _publ_contact_author_phone ' +81-839-33-5732 ' _publ_contact_author_fax ' +81-839-33-5732 ' _publ_contact_author_email ' abe@po.cc.yanaguchi-u.ac.jp ' loop_ _publ_author_name _publ_author_address ' Noritaka Abe ' ; Dpartment of Chemistry, Faculty of Science, Yamaguchi University, Yamaguchi 752-8512, Japan ; _publ_section_title ; ENTER SECTION TITLE ; _publ_section_abstract ; ENTER ABSTRACT ; _publ_section_experimental ; ENTER EXPERIMENTAL SECTION ; _publ_section_comment ; ENTER TEXT ; _publ_section_references ; Gilmore,C. J., J. Appl. Cryst., 17, 42ミ46 (1984). Johnson, C. K., ORTEP. Report ORNL-3794. Oak Ridge National Laboratory, Tennessee, USA (1965). TEXSAN: Single Crystal Structure Analysis Software, Version 2.0, (1989). Molecular Structure Corporation, The Woodlands, TX. 77381. ; _publ_section_acknowledgements ; ENTER ACKNOWLEDGEMENTS ; _publ_section_table_legends ; ENTER TABLE LEGENDS ; _publ_section_figure_captions ; ENTER FIGURE CAPTIONS ; data_triazabenz[cd]azulene(comp.25) #----------------------------------------------------------------------------- _audit_creation_date '26-FEB-99 17:58:18' _audit_creation_method 'from TEXRAY.INF file' _audit_update_record ? #----------------------------------------------------------------------------- _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'TEXSAN' _computing_structure_solution 'SIR (Burla et al.,1989)' _computing_structure_refinement 'TEXSAN' _computing_publication_material 'TEXSAN' _computing_molecular_graphics 'ORTEP (Johnson, 1965)' #----------------------------------------------------------------------------- _chemical_name_common ? _chemical_formula_weight 342.35 _chemical_formula_analytical ? _chemical_formula_sum 'C17 H18 N4 O4 ' _chemical_formula_moiety 'C17 H18 N4 O4 ' _chemical_formula_structural ? _chemical_melting_point ? #----------------------------------------------------------------------------- _cell_length_a 7.546(7) _cell_length_b 9.524(5) _cell_length_c 22.971(5) _cell_angle_alpha 90 _cell_angle_beta 92.22(3) _cell_angle_gamma 90 _cell_volume 1650(1) _cell_formula_units_Z 4 _cell_measurement_temperature 296.2 _cell_measurement_reflns_used 24 _cell_measurement_theta_min 18.9 _cell_measurement_theta_max 19.9 #----------------------------------------------------------------------------- _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/N ' _symmetry_Int_Tables_number 14 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' '1/2-x,1/2+y,1/2-z' ' -x, -y, -z' '1/2+x, 1/2+y, 1/2+z' #----------------------------------------------------------------------------- _exptl_crystal_description 'prism' _exptl_crystal_colour 'black' _exptl_crystal_size_max 0.240 _exptl_crystal_size_mid 0.420 _exptl_crystal_size_min 0.640 _exptl_crystal_density_diffrn 1.378 _exptl_crystal_density_meas 'not measured' _exptl_crystal_F_000 720.00 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type 'none' _exptl_special_details ? #----------------------------------------------------------------------------- _diffrn_special_details ? _diffrn_ambient_temperature 296.2 _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K¥a' _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device 'Rigaku AFC5S' _diffrn_measurement_method ¥w-2¥q _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% -0.60 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 3 -1 2 2 0 0 2 0 6 _diffrn_reflns_number 4315 _reflns_number_total 4315 _reflns_number_observed 1817 _reflns_observed_criterion >2.0sigma(I) _diffrn_reflns_av_R_equivalents 0.00 _diffrn_reflns_av_sigmaI/netI 0.000 _diffrn_reflns_limit_h_min ? _diffrn_reflns_limit_h_max ? _diffrn_reflns_limit_k_min ? _diffrn_reflns_limit_k_max ? _diffrn_reflns_limit_l_min ? _diffrn_reflns_limit_l_max ? _diffrn_reflns_theta_min 0.00 _diffrn_reflns_theta_max 0.00 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 0.06032 _diffrn_orient_matrix_UB_12 -0.08147 _diffrn_orient_matrix_UB_13 0.01980 _diffrn_orient_matrix_UB_21 0.04385 _diffrn_orient_matrix_UB_22 -0.03240 _diffrn_orient_matrix_UB_23 -0.03827 _diffrn_orient_matrix_UB_31 0.10966 _diffrn_orient_matrix_UB_32 0.05777 _diffrn_orient_matrix_UB_33 0.00646 #----------------------------------------------------------------------------- loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 68 0.002 0.002 'International Tables Vol IV Table 2.2A' H 0 72 0.000 0.000 'International Tables Vol IV Table 2.2A' N 0 16 0.004 0.003 'International Tables Vol IV Table 2.2A' O 0 16 0.008 0.006 'International Tables Vol IV Table 2.2A' #----------------------------------------------------------------------------- loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom O(1) 0.4370(8) 0.0641(6) 0.2975(2) 0.083(4) 1.000 Uani . . O(2) 0.5046(7) 0.1622(6) 0.2134(2) 0.077(3) 1.000 Uani . . O(3) 0.4281(7) -0.1664(5) 0.1878(2) 0.069(3) 1.000 Uani . . O(4) 0.3690(7) -0.2735(5) 0.1037(2) 0.064(3) 1.000 Uani . . N(1) 0.0694(7) 0.3183(5) -0.0060(2) 0.045(3) 1.000 Uani . . N(2) 0.1276(7) 0.2078(5) 0.0770(2) 0.041(3) 1.000 Uani . . N(3) 0.1376(7) 0.1859(6) 0.1370(2) 0.045(3) 1.000 Uani . . N(4) -0.0030(9) 0.4333(7) 0.0824(3) 0.057(4) 1.000 Uani . . C(1) 0.0608(9) 0.3271(7) 0.0511(3) 0.043(4) 1.000 Uani . . C(2) 0.2165(8) 0.0686(7) 0.1520(3) 0.039(3) 1.000 Uani . . C(3) 0.2751(8) -0.0379(6) 0.1121(3) 0.038(3) 1.000 Uani . . C(4) 0.2563(7) -0.0132(6) 0.0510(3) 0.034(3) 1.000 Uani . . C(5) 0.3086(9) -0.1067(7) 0.0057(3) 0.051(4) 1.000 Uani . . C(6) 0.3025(9) -0.0904(7) -0.0531(3) 0.054(4) 1.000 Uani . . C(7) 0.243(1) 0.0206(8) -0.0902(3) 0.056(4) 1.000 Uani . . C(8) 0.1734(9) 0.1440(7) -0.0750(3) 0.048(4) 1.000 Uani . . C(9) 0.1442(8) 0.1886(6) -0.0177(3) 0.039(3) 1.000 Uani . . C(10) 0.1816(8) 0.1149(7) 0.0342(3) 0.037(3) 1.000 Uani . . C(11) 0.2255(9) 0.0549(7) 0.2173(3) 0.047(4) 1.000 Uani . . C(12) 0.397(1) 0.0912(8) 0.2475(3) 0.057(4) 1.000 Uani . . C(13) 0.679(1) 0.212(1) 0.2394(5) 0.107(8) 1.000 Uani . . C(14A) 0.746(2) 0.312(4) 0.206(1) 0.08(1) 0.585 Uani . . C(14B) 0.689(7) 0.347(2) 0.242(3) 0.11(3) 0.415 Uani . . C(15) 0.3617(9) -0.1623(7) 0.1384(3) 0.046(4) 1.000 Uani . . C(16) 0.460(1) -0.3977(8) 0.1272(3) 0.072(5) 1.000 Uani . . C(17) 0.488(1) -0.492(1) 0.0771(4) 0.089(6) 1.000 Uani . . H(1) -0.032(7) 0.516(6) 0.059(2) 0.05(1) 1.000 Uiso . . H(2) 0.018(7) 0.431(6) 0.122(2) 0.05(2) 1.000 Uiso . . H(3) 0.35473 -0.19421 0.01895 0.06111 1.000 Uiso . . H(4) 0.34735 -0.16808 -0.07338 0.06640 1.000 Uiso . . H(5) 0.25335 0.00508 -0.13119 0.06681 1.000 Uiso . . H(6) 0.14208 0.20669 -0.10558 0.05821 1.000 Uiso . . H(7) 0.13663 0.11626 0.23186 0.05694 1.000 Uiso . . H(8) 0.19676 -0.03881 0.22654 0.05694 1.000 Uiso . . H(14) 0.56522 -0.37568 0.14730 0.09351 1.000 Uiso . . H(15) 0.38152 -0.44554 0.15417 0.09351 1.000 Uiso . . H(16) 0.37786 -0.51379 0.05747 0.10887 1.000 Uiso . . H(17) 0.56149 -0.44381 0.05055 0.10887 1.000 Uiso . . H(18) 0.54472 -0.57553 0.08969 0.10887 1.000 Uiso . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O(1) 0.102(4) 0.108(4) 0.037(3) 0.021(3) -0.017(2) 0.009(3) O(2) 0.082(4) 0.083(4) 0.062(3) -0.027(3) -0.025(3) 0.020(3) O(3) 0.103(4) 0.057(3) 0.047(3) 0.017(3) -0.023(2) 0.001(2) O(4) 0.094(4) 0.046(3) 0.051(3) 0.014(2) -0.011(2) -0.002(2) N(1) 0.058(3) 0.039(3) 0.039(3) 0.000(2) -0.005(2) 0.001(2) N(2) 0.051(3) 0.036(3) 0.036(3) 0.006(2) -0.001(2) 0.001(2) N(3) 0.057(3) 0.046(3) 0.031(3) -0.004(3) 0.003(2) 0.002(2) N(4) 0.090(5) 0.048(3) 0.034(3) 0.017(3) 0.001(3) 0.002(3) C(1) 0.050(4) 0.038(4) 0.040(4) 0.002(3) -0.004(3) 0.004(3) C(2) 0.032(3) 0.042(4) 0.043(3) -0.003(3) 0.002(2) 0.009(3) C(3) 0.038(3) 0.038(3) 0.038(3) 0.004(3) -0.002(2) 0.003(2) C(4) 0.022(3) 0.037(3) 0.043(4) -0.005(2) -0.003(2) -0.003(3) C(5) 0.066(4) 0.049(4) 0.038(4) 0.000(3) -0.003(3) -0.002(3) C(6) 0.067(5) 0.045(4) 0.050(4) 0.006(3) 0.004(3) -0.011(3) C(7) 0.073(5) 0.063(5) 0.034(4) -0.002(4) 0.006(3) -0.006(3) C(8) 0.063(4) 0.046(4) 0.035(3) -0.009(3) -0.001(3) 0.002(3) C(9) 0.040(3) 0.040(3) 0.038(3) -0.012(3) -0.004(2) -0.001(3) C(10) 0.038(3) 0.042(3) 0.032(3) -0.013(3) 0.000(2) -0.002(2) C(11) 0.050(4) 0.053(4) 0.038(3) 0.000(3) 0.005(3) 0.005(3) C(12) 0.079(5) 0.046(4) 0.044(4) 0.006(4) -0.008(4) -0.001(3) C(13) 0.096(7) 0.101(8) 0.116(8) -0.028(7) -0.071(6) 0.018(7) C(14A) 0.06(1) 0.11(2) 0.07(1) -0.04(1) 0.00(1) 0.00(1) C(14B) 0.14(3) 0.04(1) 0.14(5) 0.02(1) -0.08(3) -0.02(1) C(15) 0.050(4) 0.042(4) 0.045(4) -0.005(3) 0.001(3) -0.002(3) C(16) 0.098(6) 0.051(4) 0.067(5) 0.026(4) -0.007(4) 0.008(4) C(17) 0.101(7) 0.072(5) 0.093(7) 0.028(5) 0.000(5) -0.015(5) #----------------------------------------------------------------------------- _refine_special_details ? _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme ' w = 1/[¥s^2^(Fo) + 0.000225|Fo|^2^]' _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method Zachariasen_type_2_Gaussian_isotropic _refine_ls_extinction_coef 0.00000 _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1817 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_number_constraints ? _refine_ls_R_factor_all ? _refine_ls_R_factor_obs 0.0811 _refine_ls_wR_factor_all ? _refine_ls_wR_factor_obs 0.1087 _refine_ls_goodness_of_fit_all ? _refine_ls_goodness_of_fit_obs 3.127 _refine_ls_shift/esd_max 0.3553 _refine_ls_shift/esd_mean ? _refine_diff_density_min -0.32 _refine_diff_density_max 0.41 ----------------------------------------------------------------------------- _geom_special_details ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C12 1.203(8) . . yes O2 C12 1.336(9) . . yes O2 C13 1.499(9) . . yes O3 C15 1.222(7) . . yes O4 C15 1.328(7) . . yes O4 C16 1.460(8) . . yes N1 C1 1.319(8) . . yes N1 C9 1.389(8) . . yes N2 N3 1.393(7) . . yes N2 C1 1.370(8) . . yes N2 C10 1.395(7) . . yes N3 C2 1.305(8) . . yes N4 C1 1.340(8) . . yes N4 H1 0.97(6) . . yes N4 H2 0.91(6) . . yes C2 C3 1.448(8) . . yes C2 C11 1.505(8) . . yes C3 C4 1.424(8) . . yes C3 C15 1.472(9) . . yes C4 C5 1.436(8) . . yes C4 C10 1.392(8) . . yes C5 C6 1.360(9) . . yes C5 H3 0.949 . . yes C6 C7 1.42(1) . . yes C6 H4 0.944 . . yes C7 C8 1.340(9) . . yes C7 H5 0.959 . . yes C8 C9 1.408(8) . . yes C8 H6 0.944 . . yes C9 C10 1.404(8) . . yes C11 C12 1.484(9) . . yes C11 H7 0.960 . . yes C11 H8 0.945 . . yes C13 C14A 1.34(2) . . yes C13 C14B 1.29(2) . . yes C14A C14B 1.02(6) . . yes C16 C17 1.48(1) . . yes C16 H14 0.929 . . yes C16 H15 0.984 . . yes C17 H16 0.953 . . yes C17 H17 0.958 . . yes C17 H18 0.941 . . yes #----------------------------------------------------------------------------- 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 O2 C13 118.0(7) . . . yes C15 O4 C16 116.9(5) . . . yes C1 N1 C9 106.6(5) . . . yes N3 N2 C1 123.9(5) . . . yes N3 N2 C10 126.6(5) . . . yes C1 N2 C10 109.4(5) . . . yes N2 N3 C2 113.2(5) . . . yes C1 N4 H1 113(4) . . . yes C1 N4 H2 117(4) . . . yes H1 N4 H2 127(6) . . . yes N1 C1 N2 110.3(6) . . . yes N1 C1 N4 127.8(6) . . . yes N2 C1 N4 121.8(6) . . . yes N3 C2 C3 125.5(6) . . . yes N3 C2 C11 109.8(6) . . . yes C3 C2 C11 124.5(6) . . . yes C2 C3 C4 119.1(5) . . . yes C2 C3 C15 116.5(5) . . . yes C4 C3 C15 124.3(6) . . . yes C3 C4 C5 126.3(6) . . . yes C3 C4 C10 116.2(5) . . . yes C5 C4 C10 117.5(5) . . . yes C4 C5 C6 130.5(6) . . . yes C4 C5 H3 114.86 . . . yes C6 C5 H3 114.60 . . . yes C5 C6 C7 132.9(6) . . . yes C5 C6 H4 113.70 . . . yes C7 C6 H4 113.44 . . . yes C6 C7 C8 128.0(6) . . . yes C6 C7 H5 116.14 . . . yes C8 C7 H5 115.89 . . . yes C7 C8 C9 125.8(6) . . . yes C7 C8 H6 116.83 . . . yes C9 C8 H6 117.39 . . . yes N1 C9 C8 122.0(6) . . . yes N1 C9 C10 110.4(5) . . . yes C8 C9 C10 127.6(6) . . . yes N2 C10 C4 119.1(5) . . . yes N2 C10 C9 103.2(5) . . . yes C4 C10 C9 137.7(6) . . . yes C2 C11 C12 116.9(6) . . . yes C2 C11 H7 106.81 . . . yes C2 C11 H8 107.70 . . . yes C12 C11 H7 107.62 . . . yes C12 C11 H8 108.57 . . . yes H7 C11 H8 109.09 . . . yes O1 C12 O2 122.1(7) . . . yes O1 C12 C11 125.4(8) . . . yes O1 C12 C11 125.4(8) . . . yes O2 C12 C11 112.4(6) . . . yes O2 C13 C14A 110(1) . . . yes O2 C13 C14B 113(2) . . . yes C14A C13 C14B 45(3) . . . yes C13 C14A C14B 65(2) . . . yes C13 C14B C14A 70(2) . . . yes O3 C15 O4 120.5(6) . . . yes O3 C15 C3 124.5(6) . . . yes O4 C15 C3 115.0(6) . . . yes O4 C16 C17 106.5(6) . . . yes O4 C16 H14 112.45 . . . yes O4 C16 H15 108.94 . . . yes C17 C16 H14 112.06 . . . yes C17 C16 H15 108.37 . . . yes H14 C16 H15 108.39 . . . yes C16 C17 H16 110.40 . . . yes C16 C17 H17 107.83 . . . yes C16 C17 H18 110.56 . . . yes H16 C17 H17 108.52 . . . yes H16 C17 H18 109.97 . . . yes H17 C17 H18 109.50 . . . yes #----------------------------------------------------------------------------- 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 O1 C12 O2 C13 -2(1) . . . . yes O1 C12 C11 C2 -166.6(7) . . . . yes O2 C12 C11 C2 14.8(9) . . . . yes O2 C13 C14A C14B 103(2) . . . . yes O2 C13 C14B C14A -96(3) . . . . yes O3 C15 O4 C16 0(1) . . . . yes O3 C15 C3 C2 -20(1) . . . . yes O3 C15 C3 C4 155.9(7) . . . . yes O4 C15 C3 C2 161.9(5) . . . . yes O4 C15 C3 C4 -22.1(9) . . . . yes N1 C1 N2 N3 179.6(5) . . . . yes N1 C1 N2 C10 -0.6(7) . . . . yes N1 C9 C8 C7 -179.5(7) . . . . yes N1 C9 C10 N2 -0.7(6) . . . . yes N1 C9 C10 C4 -178.6(7) . . . . yes N2 N3 C2 C3 -5.6(8) . . . . yes N2 N3 C2 C11 178.6(5) . . . . yes N2 C1 N1 C9 0.1(7) . . . . yes N2 C10 C4 C3 -1.3(8) . . . . yes N2 C10 C4 C5 179.4(5) . . . . yes N2 C10 C9 C8 179.6(6) . . . . yes N3 N2 C1 N4 -1(1) . . . . yes N3 N2 C10 C4 -1.0(9) . . . . yes N3 N2 C10 C9 -179.4(5) . . . . yes N3 C2 C3 C4 3.7(9) . . . . yes N3 C2 C3 C15 179.9(6) . . . . yes N3 C2 C11 C12 -100.3(7) . . . . yes N4 C1 N1 C9 -179.5(7) . . . . yes N4 C1 N2 C10 179.1(6) . . . . yes C1 N1 C9 C8 -179.9(6) . . . . yes C1 N1 C9 C10 0.4(7) . . . . yes C1 N2 N3 C2 -175.8(6) . . . . yes C1 N2 C10 C4 179.1(5) . . . . yes C1 N2 C10 C9 0.7(6) . . . . yes C2 N3 N2 C10 4.4(8) . . . . yes C2 C3 C4 C5 179.5(6) . . . . yes C2 C3 C4 C10 0.2(8) . . . . yes C3 C2 C11 C12 83.9(8) . . . . yes C3 C4 C5 C6 -177.1(7) . . . . yes C3 C4 C10 C9 176.4(7) . . . . yes C3 C15 O4 C16 177.7(6) . . . . yes C4 C3 C2 C11 178.8(6) . . . . yes C4 C5 C6 C7 0(1) . . . . yes C4 C10 C9 C8 2(1) . . . . yes C5 C4 C3 C15 4(1) . . . . yes C5 C4 C10 C9 -3(1) . . . . yes C5 C6 C7 C8 -1(1) . . . . yes C6 C5 C4 C10 2(1) . . . . yes C6 C7 C8 C9 0(1) . . . . yes C7 C8 C9 C10 0(1) . . . . yes C10 C4 C3 C15 -175.7(6) . . . . yes C11 C2 C3 C15 -5.0(9) . . . . yes C11 C12 O2 C13 177.1(7) . . . . yes C12 O2 C13 C14A -163(2) . . . . yes C12 O2 C13 C14B -114(5) . . . . yes C15 O4 C16 C17 -166.7(7) . . . . yes #----------------------------------------------------------------------------- _publ_requested_journal ' ENTER JOURNAL NAME HERE ' _publ_contact_author ENTER NAME ENTER ADDRESS _publ_contact_letter ENTER TEXT OF LETTER _publ_requested_coeditor_name ? _publ_contact_author_phone ' ENTER PHONE NUMBER ' _publ_contact_author_fax ' ENTER FAX NUMBER ' _publ_contact_author_email ' ENTER EMAIL ADDRESS ' loop_ _publ_author_name _publ_author_address FIRST AUTHORS NAME ' FIRST AUTHORS ADDRESS _publ_section_title ENTER SECTION TITLE _publ_section_abstract ENTER ABSTRACT _publ_section_experimental ENTER EXPERIMENTAL SECTION _publ_section_comment ENTER TEXT _publ_section_references Burla, M. C., Camalli, M., Cascarano, G., Giacovazzo, C., Polidoli, G., Spagna, R., & Viterbo, D., J. Appl. Cryst. 22, 389-393 (1989). Johnson, C. K., ORTEP. Report ORNL-3794. Oak Ridge National Laboratory, Tennessee, USA (1965). TEXSAN: Single Crystal Structure Analysis Software, Version 2.0, (1989). Molecular Structure Corporation, The Woodlands, TX. 77381. _publ_section_acknowledgements ENTER ACKNOWLEDGEMENTS _publ_section_table_legends ENTER TABLE LEGENDS _publ_section_figure_captions ENTER FIGURE CAPTIONS