# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 188 _publ_requested_journal 'Perkin Transactions 2' loop_ _publ_author_name 'Yutronic, Nicolas' 'Garland, M. Teresa' 'Gonzalez, Guillermo' 'Merchan, Juan' _publ_contact_author_name 'Dr Nicolas Yutronic' _publ_contact_author_address ; Department of Chemistry, Faculty of Sciences Universidad de Chilie Casilla Santiago 653 CHILE ; _publ_contact_author_email 'NYUTRONI@UCHILE.CL' _publ_section_title ; Bis(quinuclidine) protonated included in layered bis(urea)-bromide and -iodide hosts. New ternary urea inclusion compounds ; data_(2) _database_code_CSD 177892 _audit_creation_method SHELXL-97 _chemical_name_systematic ; (Bis-quinuclidine-protonated) (urea-iodide) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(C7 H13.5 I.5 N), (C H4 N2 O)' _chemical_formula_iupac '(C O N2 H4)2, (C7 H13 N)2, (H +), (I -)' _chemical_formula_sum 'C8 H17.5 I.5 N3 O' _chemical_formula_weight 235.2 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' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Mn' 'Mn' 0.3368 0.7283 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 20.51(11) _cell_length_b 7.34(3) _cell_length_c 8.17(4) _cell_angle_alpha 90.00 _cell_angle_beta 111.81(8) _cell_angle_gamma 90.00 _cell_volume 1095.0(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.14 _cell_measurement_theta_max 24.99 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.369 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 484 _exptl_absorpt_coefficient_mu 1.423 _exptl_absorpt_correction_type 'empirical from intensities' _exptl_absorpt_process_details 'SADABS in SAINT_NT V6.02a (Bruker, 2000)' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _diffrn_ambient_temperature 293(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 'Smart Apex' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2184 _diffrn_reflns_av_R_equivalents 0.0382 _diffrn_reflns_av_sigmaI/netI 0.0439 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1094 _reflns_number_gt 716 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART-NT V5.624 (Bruker, 2001)' _computing_cell_refinement 'SMART-NT V5.624 (Bruker, 2001)' _computing_data_reduction 'SAINT-NT V6.02a (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP in SHELXTL/PC(Sheldrick,1994)' _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^)+(0.0728P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1094 _refine_ls_number_parameters 119 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.0708 _refine_ls_R_factor_gt 0.0409 _refine_ls_wR_factor_ref 0.1163 _refine_ls_wR_factor_gt 0.1015 _refine_ls_goodness_of_fit_ref 0.002 _refine_ls_restrained_S_all 0.996 _refine_ls_shift/su_max 0.278 _refine_ls_shift/su_mean 0.066 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 I1 I 0.5000 0.0234(4) 0.5000 0.1276(7) Uani 1 d S . . O1 O 0.6699(10) -0.125(2) 0.843(2) 0.119(5) Uani 1 d . . . N1 N 0.4447(4) 0.523(3) 0.8501(8) 0.101(3) Uani 1 d D . . N2 N 0.6691(5) 0.1823(13) 0.8457(14) 0.055(3) Uani 1 d D . . H2B H 0.6874 0.2865 0.8852 0.065 Uiso 1 calc R . . H2C H 0.6282 0.1766 0.7631 0.065 Uiso 1 calc R . . N3 N 0.7618(3) 0.030(3) 1.0285(7) 0.0682(18) Uani 1 d D . . H3A H 0.7833 0.1286 1.0742 0.082 Uiso 1 calc R . . H3B H 0.7813 -0.0742 1.0652 0.082 Uiso 1 calc R . . C1 C 0.3997(11) 0.369(4) 0.853(3) 0.188(18) Uani 1 d D . . H1A H 0.3778 0.3946 0.9378 0.225 Uiso 1 calc R . . H1B H 0.4284 0.2612 0.8925 0.225 Uiso 1 calc R . . C2 C 0.3414(13) 0.332(4) 0.670(3) 0.133(9) Uani 1 d D . . H2A H 0.3530 0.2251 0.6157 0.160 Uiso 1 calc R . . H2D H 0.2965 0.3114 0.6809 0.160 Uiso 1 calc R . . C3 C 0.3385(6) 0.497(4) 0.5614(16) 0.123(8) Uani 1 d D . . H3C H 0.2978 0.4917 0.4502 0.147 Uiso 1 calc R . . C4 C 0.3340(11) 0.661(5) 0.665(3) 0.175(16) Uani 1 d D . . H4A H 0.2956 0.6457 0.7055 0.210 Uiso 1 calc R . . H4B H 0.3237 0.7672 0.5880 0.210 Uiso 1 calc R . . C5 C 0.4033(13) 0.696(4) 0.826(3) 0.192(18) Uani 1 d D . . H5A H 0.4290 0.7977 0.8040 0.230 Uiso 1 calc R . . H5B H 0.3931 0.7226 0.9309 0.230 Uiso 1 calc R . . C6 C 0.4050(4) 0.508(4) 0.5265(10) 0.088(3) Uani 1 d D . . H6A H 0.4051 0.6182 0.4613 0.105 Uiso 1 calc R . . H6B H 0.4080 0.4044 0.4557 0.105 Uiso 1 calc R . . C7 C 0.4682(4) 0.508(4) 0.7015(9) 0.077(3) Uani 1 d D . . H7A H 0.4948 0.3963 0.7123 0.093 Uiso 1 calc R . . H7B H 0.4988 0.6096 0.7037 0.093 Uiso 1 calc R . . C8 C 0.7026(4) 0.036(2) 0.9095(9) 0.053(2) Uani 1 d D . . HQ H 0.5000 0.47(3) 1.0000 0.11(5) 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 I1 0.0644(5) 0.0576(6) 0.1843(11) 0.000 -0.0424(5) 0.000 O1 0.121(12) 0.068(8) 0.137(10) 0.039(8) 0.011(9) 0.023(8) N1 0.068(4) 0.182(10) 0.057(4) -0.014(17) 0.026(3) 0.018(19) N2 0.042(5) 0.036(6) 0.059(5) 0.019(4) -0.011(4) 0.015(4) N3 0.068(3) 0.026(3) 0.065(3) -0.011(7) -0.028(2) 0.004(7) C1 0.086(13) 0.32(5) 0.127(16) 0.10(2) -0.001(11) -0.06(2) C2 0.121(18) 0.158(19) 0.122(16) 0.055(14) 0.047(13) -0.027(14) C3 0.079(6) 0.17(2) 0.094(7) -0.047(19) 0.003(5) 0.002(16) C4 0.057(8) 0.29(5) 0.139(18) 0.00(2) -0.006(10) 0.052(16) C5 0.15(2) 0.33(5) 0.091(13) -0.04(2) 0.039(15) 0.12(3) C6 0.096(6) 0.097(9) 0.067(4) 0.015(11) 0.026(4) 0.020(13) C7 0.076(4) 0.093(8) 0.068(4) 0.008(11) 0.032(4) -0.007(12) C8 0.063(3) 0.025(5) 0.062(4) -0.011(6) 0.011(3) -0.006(6) _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 O1 C8 1.37(2) . ? N1 C1 1.465(17) . ? N1 C7 1.467(11) . ? N1 C5 1.498(18) . ? N2 C8 1.275(17) . ? N3 C8 1.243(10) . ? C1 C2 1.56(2) . ? C2 C3 1.491(18) . ? C3 C4 1.491(18) . ? C3 C6 1.495(15) . ? C4 C5 1.56(2) . ? C6 C7 1.532(12) . ? 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 C7 111.1(13) . . ? C1 N1 C5 108.9(10) . . ? C7 N1 C5 107.7(12) . . ? N1 C1 C2 112.5(14) . . ? C3 C2 C1 105.9(18) . . ? C2 C3 C4 108.7(10) . . ? C2 C3 C6 108.5(13) . . ? C4 C3 C6 108.5(14) . . ? C3 C4 C5 112.5(15) . . ? N1 C5 C4 105.3(18) . . ? C3 C6 C7 109.8(8) . . ? N1 C7 C6 110.3(8) . . ? N3 C8 N2 125.1(17) . . ? N3 C8 O1 117.8(17) . . ? N2 C8 O1 117.2(7) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.383 _refine_diff_density_min -0.431 _refine_diff_density_rms 0.063 data_(1) _database_code_CSD 177893 _audit_creation_method SHELXL-97 _chemical_name_systematic ; (Bis-quinuclidine-protonated) (urea-bromide) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(C7 H13.5 Br.5 N), (C H4 N2 O)' _chemical_formula_iupac '(C O N2 H4)2, (C7 H13 N)2, (H +), (Br -)' _chemical_formula_sum 'C8 H17.5 Br.5 N3 O' _chemical_formula_weight 211.7 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' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Mn' 'Mn' 0.3368 0.7283 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 19.323(8) _cell_length_b 7.145(3) _cell_length_c 8.566(4) _cell_angle_alpha 90.00 _cell_angle_beta 112.19(3) _cell_angle_gamma 90.00 _cell_volume 1095.0(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 25.02 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.284 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 1.897 _exptl_absorpt_correction_type 'empirical from intensities' _exptl_absorpt_process_details 'SADABS in SAINT_NT V6.02a (Bruker, 2000)' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _diffrn_ambient_temperature 293(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 'Smart Apex' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1046 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1289 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 25.02 _reflns_number_total 1046 _reflns_number_gt 472 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART-NT V5.624 (Bruker, 2001)' _computing_cell_refinement 'SMART-NT V5.624 (Bruker, 2001)' _computing_data_reduction 'SAINT-NT V6.02a (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP in SHELXTL/PC(Sheldrick,1994)' _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^)+(0.0728P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1046 _refine_ls_number_parameters 119 _refine_ls_number_restraints 36 _refine_ls_R_factor_all 0.1787 _refine_ls_R_factor_gt 0.0607 _refine_ls_wR_factor_ref 0.1489 _refine_ls_wR_factor_gt 0.1111 _refine_ls_goodness_of_fit_ref 0.967 _refine_ls_restrained_S_all 0.971 _refine_ls_shift/su_max 0.877 _refine_ls_shift/su_mean 0.092 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 0.5000 0.3031(18) 0.0000 0.1054(10) Uani 1 2 d S . . O1 O 0.7431(4) 0.811(3) 0.4744(8) 0.085(2) Uani 1 1 d D . . N3 N 0.8368(10) 0.650(3) 0.6640(17) 0.071(7) Uani 1 1 d DU . . H3A H 0.8175 0.5447 0.6209 0.085 Uiso 1 1 calc R . . H3B H 0.8783 0.6529 0.7500 0.085 Uiso 1 1 calc R . . N2 N 0.8359(9) 0.965(3) 0.669(2) 0.084(7) Uani 1 1 d D . . H2A H 0.8159 1.0710 0.6296 0.101 Uiso 1 1 calc R . . H2B H 0.8774 0.9610 0.7550 0.101 Uiso 1 1 calc R . . C8 C 0.8028(5) 0.808(3) 0.5980(10) 0.054(3) Uani 1 1 d D . . N1 N 0.5555(4) 0.799(3) 0.6507(9) 0.079(3) Uani 1 1 d D . . H1TR H 0.5000 0.82(4) 0.5000 0.095 Uiso 1 2 d S . . C6 C 0.5852(4) 0.813(4) 0.9577(9) 0.084(4) Uani 1 1 d D . . H6A H 0.5794 0.9335 1.0034 0.100 Uiso 1 1 calc R . . H6B H 0.5821 0.7161 1.0341 0.100 Uiso 1 1 calc R . . C5 C 0.5895(13) 0.609(2) 0.673(3) 0.158(11) Uani 1 1 d DU . . H5A H 0.6044 0.5773 0.5795 0.190 Uiso 1 1 calc R . . H5B H 0.5550 0.5143 0.6811 0.190 Uiso 1 1 calc R . . C3 C 0.6606(5) 0.803(3) 0.9394(14) 0.097(5) Uani 1 1 d D . . H3C H 0.7011 0.7955 1.0505 0.116 Uiso 1 1 calc R . . C4 C 0.6578(15) 0.626(3) 0.838(3) 0.140(12) Uani 1 1 d D . . H4A H 0.6587 0.5186 0.9086 0.168 Uiso 1 1 calc R . . H4B H 0.7026 0.6205 0.8131 0.168 Uiso 1 1 calc R . . C7 C 0.5233(5) 0.785(4) 0.7828(9) 0.065(4) Uani 1 1 d D . . H7A H 0.5003 0.6634 0.7772 0.078 Uiso 1 1 calc R . . H7B H 0.4851 0.8800 0.7637 0.078 Uiso 1 1 calc R . . C1 C 0.6083(11) 0.957(3) 0.669(2) 0.138(9) Uani 1 1 d DU . . H1A H 0.5801 1.0726 0.6435 0.166 Uiso 1 1 calc R . . H1B H 0.6308 0.9415 0.5855 0.166 Uiso 1 1 calc R . . C2 C 0.6710(14) 0.974(4) 0.844(3) 0.159(15) Uani 1 1 d D . . H2C H 0.7197 0.9718 0.8355 0.190 Uiso 1 1 calc R . . H2D H 0.6661 1.0887 0.8990 0.190 Uiso 1 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 Br1 0.0737(12) 0.0553(10) 0.1222(16) 0.000 -0.0369(10) 0.000 O1 0.076(5) 0.037(4) 0.092(5) -0.021(11) -0.025(4) -0.021(12) N3 0.101(14) 0.026(10) 0.035(8) -0.006(8) -0.032(8) 0.023(10) N2 0.041(11) 0.049(13) 0.125(14) -0.007(12) -0.010(10) 0.011(10) C8 0.056(7) 0.037(5) 0.050(6) 0.006(15) -0.003(5) -0.022(17) N1 0.062(6) 0.108(8) 0.049(5) 0.037(14) 0.001(4) -0.016(17) C6 0.086(8) 0.097(9) 0.052(6) -0.008(17) 0.008(6) 0.049(19) C5 0.147(18) 0.19(2) 0.078(14) -0.001(14) -0.027(12) 0.037(17) C3 0.065(9) 0.137(12) 0.059(8) 0.02(3) -0.009(6) -0.02(2) C4 0.100(19) 0.16(3) 0.12(2) 0.00(2) -0.001(15) 0.074(17) C7 0.073(7) 0.066(11) 0.051(6) 0.013(9) 0.018(6) 0.022(10) C1 0.087(12) 0.193(18) 0.112(16) 0.071(14) 0.012(11) -0.083(13) C2 0.059(12) 0.31(4) 0.066(14) 0.04(2) -0.018(10) -0.045(19) _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 O1 C8 1.237(9) . ? N3 C8 1.320(9) . ? N2 C8 1.320(9) . ? N1 C7 1.486(3) . ? N1 C1 1.489(3) . ? N1 C5 1.490(3) . ? C6 C3 1.524(3) . ? C6 C7 1.536(3) . ? C5 C4 1.536(3) . ? C3 C2 1.524(3) . ? C3 C4 1.524(3) . ? C1 C2 1.536(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 O1 C8 N3 122.3(9) . . ? O1 C8 N2 120.9(9) . . ? N3 C8 N2 116.9(7) . . ? C7 N1 C1 116.0(11) . . ? C7 N1 C5 97.8(16) . . ? C1 N1 C5 115.2(9) . . ? C3 C6 C7 108.4(7) . . ? N1 C5 C4 103.1(13) . . ? C2 C3 C6 110.2(15) . . ? C2 C3 C4 110.1(11) . . ? C6 C3 C4 105.4(18) . . ? C3 C4 C5 115.1(14) . . ? N1 C7 C6 109.8(7) . . ? N1 C1 C2 114.7(16) . . ? C3 C2 C1 104.2(17) . . ? _diffrn_measured_fraction_theta_max 0.495 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.305 _refine_diff_density_min -0.243 _refine_diff_density_rms 0.064