# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Damir Safin' _publ_contact_author_email damir.safin@ksu.ru _publ_section_title ; Reaction of o-, m- and p-ROOCC6H4NH2 (R = Me, Et) with N,N-dimethylformamide azine dihydrochloride: Crucial influence of the intramolecular hydrogen bonding in the amine ; _publ_author_name D.Safin # Attachment '- 1.cif' data_safin4n _database_code_depnum_ccdc_archive 'CCDC 843119' #TrackingRef '- 1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H14 N4' _chemical_formula_sum 'C6 H14 N4' _chemical_formula_weight 142.21 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' 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 10.674(2) _cell_length_b 10.9232(13) _cell_length_c 8.796(2) _cell_angle_alpha 90.00 _cell_angle_beta 125.04(3) _cell_angle_gamma 90.00 _cell_volume 839.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2186 _cell_measurement_theta_min 2.8224 _cell_measurement_theta_max 25.2593 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.125 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 312 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_T_min 0.95964 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'RU200 rotating anode' _diffrn_radiation_monochromator 'Zr filter' _diffrn_measurement_device_type 'MAR345 image plate' _diffrn_measurement_method '80 images, \D\F 3.0\%' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3580 _diffrn_reflns_av_R_equivalents 0.0550 _diffrn_reflns_av_sigmaI/netI 0.0390 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.98 _diffrn_reflns_theta_max 25.31 _reflns_number_total 768 _reflns_number_gt 713 _reflns_threshold_expression >2sigma(I) _computing_data_collection MAR _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0752P)^2^+0.4162P] 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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.112(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 768 _refine_ls_number_parameters 49 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0546 _refine_ls_R_factor_gt 0.0524 _refine_ls_wR_factor_ref 0.1358 _refine_ls_wR_factor_gt 0.1331 _refine_ls_goodness_of_fit_ref 1.155 _refine_ls_restrained_S_all 1.155 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N5 N 0.22719(12) 0.20483(10) 0.03781(14) 0.0230(4) Uani 1 1 d . . . C4 C 0.32117(15) 0.20054(12) 0.21547(18) 0.0236(4) Uani 1 1 d . . . H4 H 0.4036 0.2572 0.2761 0.028 Uiso 1 1 calc R . . N1 N 0.30650(14) 0.11766(11) 0.31929(16) 0.0322(5) Uani 1 1 d . . . C2 C 0.39985(17) 0.12757(14) 0.51931(18) 0.0329(5) Uani 1 1 d . . . H2A H 0.4900 0.1779 0.5601 0.049 Uiso 1 1 calc R . . H2B H 0.4327 0.0458 0.5742 0.049 Uiso 1 1 calc R . . H2C H 0.3402 0.1658 0.5593 0.049 Uiso 1 1 calc R . . C3 C 0.17529(18) 0.03797(14) 0.2307(2) 0.0359(5) Uani 1 1 d . . . H3A H 0.0829 0.0864 0.1855 0.054 Uiso 1 1 calc R . . H3B H 0.1879 -0.0229 0.3204 0.054 Uiso 1 1 calc R . . H3C H 0.1658 -0.0038 0.1260 0.054 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 N5 0.0255(7) 0.0246(7) 0.0184(6) 0.0018(4) 0.0123(5) 0.0008(4) C4 0.0243(7) 0.0245(7) 0.0209(8) -0.0001(5) 0.0123(6) 0.0005(5) N1 0.0351(8) 0.0374(8) 0.0168(7) 0.0040(5) 0.0106(6) -0.0057(5) C2 0.0365(9) 0.0392(9) 0.0187(8) 0.0039(6) 0.0133(7) 0.0040(6) C3 0.0416(9) 0.0372(9) 0.0275(8) 0.0027(6) 0.0191(7) -0.0089(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 N5 C4 1.2848(18) . ? N5 N5 1.423(2) 7 ? C4 N1 1.3574(18) . ? C4 H4 0.9500 . ? N1 C3 1.4400(19) . ? N1 C2 1.4447(18) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? 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 C4 N5 N5 110.86(13) . 7 ? N5 C4 N1 122.11(12) . . ? N5 C4 H4 118.9 . . ? N1 C4 H4 118.9 . . ? C4 N1 C3 119.43(12) . . ? C4 N1 C2 120.27(12) . . ? C3 N1 C2 118.73(12) . . ? N1 C2 H2A 109.5 . . ? N1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? N1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? N1 C3 H3A 109.5 . . ? N1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? N1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N5 N5 C4 N1 -176.86(13) 7 . . . ? N5 C4 N1 C3 -5.0(2) . . . . ? N5 C4 N1 C2 -170.55(12) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.31 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.300 _refine_diff_density_min -0.258 _refine_diff_density_rms 0.087 # Attachment '- 2.cif' data_aror015 _database_code_depnum_ccdc_archive 'CCDC 843120' #TrackingRef '- 2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H14 N4, C9 H11 N O2' _chemical_formula_sum 'C15 H25 N5 O2' _chemical_formula_weight 307.40 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.0454(5) _cell_length_b 8.9859(19) _cell_length_c 13.0298(17) _cell_angle_alpha 92.702(14) _cell_angle_beta 100.424(10) _cell_angle_gamma 115.058(14) _cell_volume 831.1(2) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 4210 _cell_measurement_theta_min 2.5215 _cell_measurement_theta_max 25.2044 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.228 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 332 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_T_min 0.98650 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'RU200 rotating anode' _diffrn_radiation_monochromator 'Zr filter' _diffrn_measurement_device_type 'MAR345 image plate' _diffrn_measurement_method '80 images, \D\F 3.0\%' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7192 _diffrn_reflns_av_R_equivalents 0.0969 _diffrn_reflns_av_sigmaI/netI 0.0984 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.53 _diffrn_reflns_theta_max 25.26 _reflns_number_total 2819 _reflns_number_gt 2532 _reflns_threshold_expression >2sigma(I) _computing_data_collection MAR _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0705P)^2^+0.3388P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2819 _refine_ls_number_parameters 204 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0555 _refine_ls_R_factor_gt 0.0472 _refine_ls_wR_factor_ref 0.1254 _refine_ls_wR_factor_gt 0.1208 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O19 O 0.44769(17) 0.64499(14) 0.32247(9) 0.0300(3) Uani 1 1 d . . . O20 O 0.41244(15) 0.65744(13) 0.48938(8) 0.0229(3) Uani 1 1 d . . . C13 C -0.0296(2) 0.1608(2) 0.26281(12) 0.0224(4) Uani 1 1 d . . . H13 H -0.0759 0.0892 0.1977 0.027 Uiso 1 1 calc R . . C12 C 0.1274(2) 0.31702(19) 0.27285(11) 0.0196(3) Uani 1 1 d . . . C16 C 0.0993(2) 0.3660(2) 0.45348(11) 0.0217(3) Uani 1 1 d . . . H16 H 0.1423 0.4362 0.5189 0.026 Uiso 1 1 calc R . . N11 N 0.2082(2) 0.35824(18) 0.18916(10) 0.0269(3) Uani 1 1 d . . . H11A H 0.1630 0.2885 0.1303 0.032 Uiso 1 1 calc R . . H11B H 0.3059 0.4548 0.1937 0.032 Uiso 1 1 calc R . . C17 C 0.1940(2) 0.42059(19) 0.37168(11) 0.0194(3) Uani 1 1 d . . . C14 C -0.1164(2) 0.1102(2) 0.34492(12) 0.0237(4) Uani 1 1 d . . . H14 H -0.2199 0.0037 0.3363 0.028 Uiso 1 1 calc R . . C15 C -0.0538(2) 0.2139(2) 0.44127(12) 0.0245(4) Uani 1 1 d . . . H15 H -0.1161 0.1797 0.4973 0.029 Uiso 1 1 calc R . . C18 C 0.3608(2) 0.58177(19) 0.38879(11) 0.0204(3) Uani 1 1 d . . . C22 C 0.5945(2) 0.8852(2) 0.62510(12) 0.0253(4) Uani 1 1 d . . . H22A H 0.4778 0.8889 0.6339 0.038 Uiso 1 1 calc R . . H22B H 0.6984 0.9972 0.6430 0.038 Uiso 1 1 calc R . . H22C H 0.6218 0.8121 0.6718 0.038 Uiso 1 1 calc R . . C21 C 0.5724(2) 0.81985(19) 0.51231(12) 0.0229(4) Uani 1 1 d . . . H21A H 0.5500 0.8951 0.4645 0.027 Uiso 1 1 calc R . . H21B H 0.6875 0.8112 0.5029 0.027 Uiso 1 1 calc R . . N5 N 0.02381(18) 0.93207(15) 0.00209(9) 0.0183(3) Uani 1 1 d . . . N1 N 0.2726(2) 0.87293(17) 0.06996(12) 0.0292(4) Uani 1 1 d . . . C4 C 0.1944(2) 0.97865(18) 0.05396(11) 0.0197(3) Uani 1 1 d . . . H4 H 0.2681 1.0923 0.0821 0.024 Uiso 1 1 calc R . . C3 C 0.4628(2) 0.9271(2) 0.12897(13) 0.0291(4) Uani 1 1 d . . . H3A H 0.5198 1.0469 0.1519 0.044 Uiso 1 1 calc R . . H3B H 0.5361 0.9022 0.0843 0.044 Uiso 1 1 calc R . . H3C H 0.4617 0.8690 0.1908 0.044 Uiso 1 1 calc R . . C2 C 0.1671(3) 0.6984(2) 0.02754(15) 0.0321(4) Uani 1 1 d . . . H2A H 0.0457 0.6534 0.0482 0.048 Uiso 1 1 calc R . . H2B H 0.2385 0.6382 0.0552 0.048 Uiso 1 1 calc R . . H2C H 0.1457 0.6859 -0.0495 0.048 Uiso 1 1 calc R . . N10 N 0.46810(18) 0.52329(16) 0.95132(9) 0.0211(3) Uani 1 1 d . . . N6 N 0.20872(19) 0.42510(16) 0.81047(10) 0.0235(3) Uani 1 1 d . . . C9 C 0.3092(2) 0.40814(19) 0.90147(11) 0.0205(3) Uani 1 1 d . . . H9 H 0.2591 0.3063 0.9293 0.025 Uiso 1 1 calc R . . C7 C 0.0561(3) 0.2804(2) 0.74548(13) 0.0317(4) Uani 1 1 d . . . H7A H 0.1025 0.2401 0.6911 0.048 Uiso 1 1 calc R . . H7B H -0.0433 0.3096 0.7120 0.048 Uiso 1 1 calc R . . H7C H 0.0053 0.1934 0.7893 0.048 Uiso 1 1 calc R . . C8 C 0.2926(2) 0.5689(2) 0.75812(12) 0.0258(4) Uani 1 1 d . . . H8A H 0.3813 0.6640 0.8107 0.039 Uiso 1 1 calc R . . H8B H 0.1936 0.5946 0.7196 0.039 Uiso 1 1 calc R . . H8C H 0.3596 0.5454 0.7086 0.039 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 O19 0.0348(7) 0.0268(6) 0.0255(6) 0.0068(5) 0.0117(5) 0.0085(5) O20 0.0235(6) 0.0196(6) 0.0219(5) 0.0016(4) 0.0057(4) 0.0058(5) C13 0.0232(9) 0.0242(8) 0.0201(7) -0.0016(6) 0.0017(6) 0.0123(7) C12 0.0215(9) 0.0250(8) 0.0181(7) 0.0041(6) 0.0037(6) 0.0156(7) C16 0.0225(9) 0.0259(8) 0.0170(7) 0.0011(6) 0.0029(6) 0.0116(7) N11 0.0287(8) 0.0294(7) 0.0194(7) 0.0006(5) 0.0074(5) 0.0092(6) C17 0.0205(9) 0.0221(8) 0.0190(7) 0.0039(6) 0.0025(6) 0.0132(7) C14 0.0202(9) 0.0233(8) 0.0251(8) 0.0030(6) 0.0023(6) 0.0085(6) C15 0.0225(9) 0.0292(9) 0.0201(7) 0.0046(6) 0.0067(6) 0.0089(7) C18 0.0249(9) 0.0219(8) 0.0196(7) 0.0054(6) 0.0049(6) 0.0149(7) C22 0.0220(9) 0.0202(8) 0.0285(8) 0.0036(6) 0.0003(6) 0.0064(6) C21 0.0198(9) 0.0173(7) 0.0302(8) 0.0050(6) 0.0052(6) 0.0068(6) N5 0.0224(7) 0.0148(6) 0.0176(6) 0.0014(5) 0.0034(5) 0.0084(5) N1 0.0227(8) 0.0189(7) 0.0407(8) -0.0046(6) -0.0048(6) 0.0099(6) C4 0.0227(8) 0.0148(7) 0.0190(7) 0.0004(5) 0.0043(6) 0.0061(6) C3 0.0243(9) 0.0265(9) 0.0331(9) 0.0034(7) -0.0018(7) 0.0115(7) C2 0.0290(10) 0.0195(8) 0.0445(10) -0.0049(7) -0.0042(7) 0.0134(7) N10 0.0210(8) 0.0244(7) 0.0175(6) 0.0074(5) 0.0035(5) 0.0094(6) N6 0.0237(8) 0.0203(7) 0.0196(6) 0.0035(5) -0.0007(5) 0.0053(6) C9 0.0236(9) 0.0203(8) 0.0186(7) 0.0055(6) 0.0053(6) 0.0100(6) C7 0.0352(10) 0.0239(9) 0.0239(8) 0.0013(7) -0.0047(7) 0.0063(7) C8 0.0279(9) 0.0215(8) 0.0244(8) 0.0075(6) 0.0003(6) 0.0093(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 O19 C18 1.2194(19) . ? O20 C18 1.3536(18) . ? O20 C21 1.4507(19) . ? C13 C14 1.373(2) . ? C13 C12 1.416(2) . ? C13 H13 0.9500 . ? C12 N11 1.357(2) . ? C12 C17 1.424(2) . ? C16 C15 1.376(2) . ? C16 C17 1.409(2) . ? C16 H16 0.9500 . ? N11 H11A 0.8800 . ? N11 H11B 0.8800 . ? C17 C18 1.471(2) . ? C14 C15 1.401(2) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C22 C21 1.507(2) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? N5 C4 1.291(2) . ? N5 N5 1.426(2) 2_575 ? N1 C4 1.349(2) . ? N1 C3 1.441(2) . ? N1 C2 1.451(2) . ? C4 H4 0.9500 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? N10 C9 1.282(2) . ? N10 N10 1.430(2) 2_667 ? N6 C9 1.3627(19) . ? N6 C7 1.443(2) . ? N6 C8 1.450(2) . ? C9 H9 0.9500 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? 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 C18 O20 C21 116.10(12) . . ? C14 C13 C12 121.57(14) . . ? C14 C13 H13 119.2 . . ? C12 C13 H13 119.2 . . ? N11 C12 C13 118.54(14) . . ? N11 C12 C17 123.70(15) . . ? C13 C12 C17 117.74(14) . . ? C15 C16 C17 121.86(14) . . ? C15 C16 H16 119.1 . . ? C17 C16 H16 119.1 . . ? C12 N11 H11A 120.0 . . ? C12 N11 H11B 120.0 . . ? H11A N11 H11B 120.0 . . ? C16 C17 C12 119.14(14) . . ? C16 C17 C18 120.28(13) . . ? C12 C17 C18 120.57(14) . . ? C13 C14 C15 120.68(15) . . ? C13 C14 H14 119.7 . . ? C15 C14 H14 119.7 . . ? C16 C15 C14 118.99(14) . . ? C16 C15 H15 120.5 . . ? C14 C15 H15 120.5 . . ? O19 C18 O20 121.62(14) . . ? O19 C18 C17 125.88(14) . . ? O20 C18 C17 112.50(12) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? O20 C21 C22 106.85(12) . . ? O20 C21 H21A 110.4 . . ? C22 C21 H21A 110.4 . . ? O20 C21 H21B 110.4 . . ? C22 C21 H21B 110.4 . . ? H21A C21 H21B 108.6 . . ? C4 N5 N5 111.36(15) . 2_575 ? C4 N1 C3 122.02(14) . . ? C4 N1 C2 120.80(14) . . ? C3 N1 C2 117.18(13) . . ? N5 C4 N1 122.86(14) . . ? N5 C4 H4 118.6 . . ? N1 C4 H4 118.6 . . ? N1 C3 H3A 109.5 . . ? N1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? N1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N1 C2 H2A 109.5 . . ? N1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? N1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C9 N10 N10 110.64(15) . 2_667 ? C9 N6 C7 119.85(13) . . ? C9 N6 C8 119.78(13) . . ? C7 N6 C8 116.27(12) . . ? N10 C9 N6 123.02(14) . . ? N10 C9 H9 118.5 . . ? N6 C9 H9 118.5 . . ? N6 C7 H7A 109.5 . . ? N6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N6 C8 H8A 109.5 . . ? N6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? 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 C14 C13 C12 N11 179.01(14) . . . . ? C14 C13 C12 C17 0.5(2) . . . . ? C15 C16 C17 C12 1.3(2) . . . . ? C15 C16 C17 C18 -178.06(14) . . . . ? N11 C12 C17 C16 179.85(14) . . . . ? C13 C12 C17 C16 -1.7(2) . . . . ? N11 C12 C17 C18 -0.8(2) . . . . ? C13 C12 C17 C18 177.68(13) . . . . ? C12 C13 C14 C15 1.2(2) . . . . ? C17 C16 C15 C14 0.3(2) . . . . ? C13 C14 C15 C16 -1.6(2) . . . . ? C21 O20 C18 O19 2.1(2) . . . . ? C21 O20 C18 C17 -178.10(12) . . . . ? C16 C17 C18 O19 -176.03(15) . . . . ? C12 C17 C18 O19 4.6(2) . . . . ? C16 C17 C18 O20 4.16(19) . . . . ? C12 C17 C18 O20 -175.20(12) . . . . ? C18 O20 C21 C22 175.65(12) . . . . ? N5 N5 C4 N1 179.37(15) 2_575 . . . ? C3 N1 C4 N5 -179.40(15) . . . . ? C2 N1 C4 N5 0.8(2) . . . . ? N10 N10 C9 N6 174.51(15) 2_667 . . . ? C7 N6 C9 N10 165.13(15) . . . . ? C8 N6 C9 N10 8.7(2) . . . . ? _diffrn_measured_fraction_theta_max 0.935 _diffrn_reflns_theta_full 25.26 _diffrn_measured_fraction_theta_full 0.935 _refine_diff_density_max 0.336 _refine_diff_density_min -0.443 _refine_diff_density_rms 0.102 # Attachment '- 3.cif' data_ar024 _database_code_depnum_ccdc_archive 'CCDC 846923' #TrackingRef '- 3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H11 N3 O2' _chemical_formula_sum 'C11 H11 N3 O2' _chemical_formula_weight 217.23 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' 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 18.5835(14) _cell_length_b 5.4789(5) _cell_length_c 20.2394(19) _cell_angle_alpha 90.00 _cell_angle_beta 90.425(8) _cell_angle_gamma 90.00 _cell_volume 2060.7(3) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3300 _cell_measurement_theta_min 2.0084 _cell_measurement_theta_max 25.2716 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.400 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 912 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_T_min 0.98021 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'RU200 rotating anode' _diffrn_radiation_monochromator 'Zr filter' _diffrn_measurement_device_type 'MAR345 image plate' _diffrn_measurement_method '100 images, \D\F 2.5\%' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8920 _diffrn_reflns_av_R_equivalents 0.0428 _diffrn_reflns_av_sigmaI/netI 0.0260 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 25.33 _reflns_number_total 1871 _reflns_number_gt 1619 _reflns_threshold_expression >2sigma(I) _computing_data_collection MAR _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0538P)^2^+1.2805P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1871 _refine_ls_number_parameters 146 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0431 _refine_ls_R_factor_gt 0.0361 _refine_ls_wR_factor_ref 0.1023 _refine_ls_wR_factor_gt 0.0979 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.80442(7) 0.3458(3) 0.70681(7) 0.0222(3) Uani 1 1 d . . . H1 H 0.7597 0.4186 0.7177 0.027 Uiso 1 1 calc R . . N2 N 0.83306(6) 0.1625(2) 0.73854(6) 0.0254(3) Uani 1 1 d . . . N3 N 0.89820(7) 0.1093(2) 0.70750(6) 0.0290(3) Uani 1 1 d . . . C4 C 0.90465(8) 0.2645(3) 0.65916(7) 0.0257(3) Uani 1 1 d . . . H4 H 0.9443 0.2693 0.6299 0.031 Uiso 1 1 calc R . . N5 N 0.84709(6) 0.4197(2) 0.65586(5) 0.0194(3) Uani 1 1 d . . . C6 C 0.83417(7) 0.6149(2) 0.61030(7) 0.0189(3) Uani 1 1 d . . . C7 C 0.77473(7) 0.7658(3) 0.61951(7) 0.0233(3) Uani 1 1 d . . . H7 H 0.7425 0.7359 0.6548 0.028 Uiso 1 1 calc R . . C8 C 0.76303(8) 0.9596(3) 0.57681(7) 0.0263(3) Uani 1 1 d . . . H8 H 0.7226 1.0629 0.5829 0.032 Uiso 1 1 calc R . . C9 C 0.80982(8) 1.0038(3) 0.52535(7) 0.0246(3) Uani 1 1 d . . . H9 H 0.8020 1.1389 0.4967 0.030 Uiso 1 1 calc R . . C10 C 0.86841(7) 0.8502(2) 0.51553(7) 0.0199(3) Uani 1 1 d . . . C11 C 0.88080(7) 0.6537(2) 0.55794(7) 0.0194(3) Uani 1 1 d . . . H11 H 0.9205 0.5478 0.5511 0.023 Uiso 1 1 calc R . . C12 C 0.91920(7) 0.8884(3) 0.45958(7) 0.0205(3) Uani 1 1 d . . . O13 O 0.97301(5) 0.76868(19) 0.45147(5) 0.0296(3) Uani 1 1 d . . . O14 O 0.89788(5) 1.06783(18) 0.41928(5) 0.0248(3) Uani 1 1 d . . . C15 C 0.94404(8) 1.1185(3) 0.36267(7) 0.0247(3) Uani 1 1 d . . . H15A H 0.9458 0.9749 0.3330 0.030 Uiso 1 1 calc R . . H15B H 0.9936 1.1561 0.3778 0.030 Uiso 1 1 calc R . . C16 C 0.91225(9) 1.3340(3) 0.32688(8) 0.0306(4) Uani 1 1 d . . . H16A H 0.8632 1.2946 0.3123 0.046 Uiso 1 1 calc R . . H16B H 0.9418 1.3730 0.2884 0.046 Uiso 1 1 calc R . . H16C H 0.9110 1.4750 0.3567 0.046 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 C1 0.0188(7) 0.0269(8) 0.0210(7) 0.0001(6) 0.0075(6) -0.0007(6) N2 0.0223(6) 0.0296(7) 0.0244(7) 0.0023(5) 0.0081(5) 0.0000(5) N3 0.0229(6) 0.0367(7) 0.0276(7) 0.0079(6) 0.0097(5) 0.0057(5) C4 0.0187(7) 0.0342(8) 0.0244(8) 0.0074(6) 0.0083(6) 0.0058(6) N5 0.0169(6) 0.0232(6) 0.0183(6) 0.0001(5) 0.0049(4) 0.0005(4) C6 0.0173(7) 0.0223(7) 0.0172(7) -0.0011(5) 0.0010(5) -0.0018(5) C7 0.0191(7) 0.0310(8) 0.0199(7) -0.0017(6) 0.0060(5) 0.0013(6) C8 0.0224(7) 0.0308(8) 0.0258(8) -0.0005(6) 0.0054(6) 0.0091(6) C9 0.0232(7) 0.0270(7) 0.0237(8) 0.0031(6) 0.0024(6) 0.0052(6) C10 0.0178(7) 0.0246(7) 0.0175(7) -0.0013(5) 0.0013(5) 0.0005(5) C11 0.0155(6) 0.0226(7) 0.0200(7) -0.0028(5) 0.0017(5) 0.0011(5) C12 0.0175(7) 0.0239(7) 0.0202(7) -0.0005(5) 0.0013(5) 0.0005(5) O13 0.0254(6) 0.0362(6) 0.0275(6) 0.0068(4) 0.0114(4) 0.0098(4) O14 0.0214(5) 0.0306(6) 0.0224(5) 0.0071(4) 0.0062(4) 0.0044(4) C15 0.0211(7) 0.0334(8) 0.0197(7) 0.0033(6) 0.0059(6) -0.0007(6) C16 0.0337(8) 0.0314(8) 0.0268(8) 0.0059(6) 0.0067(6) -0.0003(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 C1 N2 1.3033(18) . ? C1 N5 1.3669(17) . ? C1 H1 0.9500 . ? N2 N3 1.3988(16) . ? N3 C4 1.3027(19) . ? C4 N5 1.3678(18) . ? C4 H4 0.9500 . ? N5 C6 1.4314(17) . ? C6 C11 1.3902(19) . ? C6 C7 1.3932(19) . ? C7 C8 1.385(2) . ? C7 H7 0.9500 . ? C8 C9 1.383(2) . ? C8 H8 0.9500 . ? C9 C10 1.3916(19) . ? C9 H9 0.9500 . ? C10 C11 1.395(2) . ? C10 C12 1.4941(19) . ? C11 H11 0.9500 . ? C12 O13 1.2081(16) . ? C12 O14 1.3357(17) . ? O14 C15 1.4629(16) . ? C15 C16 1.504(2) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? 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 C1 N5 111.28(12) . . ? N2 C1 H1 124.4 . . ? N5 C1 H1 124.4 . . ? C1 N2 N3 106.92(11) . . ? C4 N3 N2 106.61(12) . . ? N3 C4 N5 111.49(12) . . ? N3 C4 H4 124.3 . . ? N5 C4 H4 124.3 . . ? C1 N5 C4 103.70(11) . . ? C1 N5 C6 127.74(11) . . ? C4 N5 C6 128.56(11) . . ? C11 C6 C7 120.71(13) . . ? C11 C6 N5 120.19(12) . . ? C7 C6 N5 119.10(12) . . ? C8 C7 C6 119.48(13) . . ? C8 C7 H7 120.3 . . ? C6 C7 H7 120.3 . . ? C9 C8 C7 120.49(13) . . ? C9 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? C8 C9 C10 119.90(13) . . ? C8 C9 H9 120.0 . . ? C10 C9 H9 120.0 . . ? C9 C10 C11 120.31(13) . . ? C9 C10 C12 121.53(13) . . ? C11 C10 C12 118.16(12) . . ? C6 C11 C10 119.08(13) . . ? C6 C11 H11 120.5 . . ? C10 C11 H11 120.5 . . ? O13 C12 O14 123.96(13) . . ? O13 C12 C10 123.72(13) . . ? O14 C12 C10 112.31(11) . . ? C12 O14 C15 116.41(10) . . ? O14 C15 C16 107.19(11) . . ? O14 C15 H15A 110.3 . . ? C16 C15 H15A 110.3 . . ? O14 C15 H15B 110.3 . . ? C16 C15 H15B 110.3 . . ? H15A C15 H15B 108.5 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N5 C1 N2 N3 -0.15(16) . . . . ? C1 N2 N3 C4 0.16(16) . . . . ? N2 N3 C4 N5 -0.11(17) . . . . ? N2 C1 N5 C4 0.08(15) . . . . ? N2 C1 N5 C6 -179.61(12) . . . . ? N3 C4 N5 C1 0.03(16) . . . . ? N3 C4 N5 C6 179.72(13) . . . . ? C1 N5 C6 C11 -175.01(12) . . . . ? C4 N5 C6 C11 5.4(2) . . . . ? C1 N5 C6 C7 5.5(2) . . . . ? C4 N5 C6 C7 -174.16(13) . . . . ? C11 C6 C7 C8 -1.5(2) . . . . ? N5 C6 C7 C8 178.08(12) . . . . ? C6 C7 C8 C9 0.0(2) . . . . ? C7 C8 C9 C10 1.2(2) . . . . ? C8 C9 C10 C11 -0.9(2) . . . . ? C8 C9 C10 C12 178.55(13) . . . . ? C7 C6 C11 C10 1.7(2) . . . . ? N5 C6 C11 C10 -177.84(12) . . . . ? C9 C10 C11 C6 -0.5(2) . . . . ? C12 C10 C11 C6 -179.98(11) . . . . ? C9 C10 C12 O13 175.45(14) . . . . ? C11 C10 C12 O13 -5.1(2) . . . . ? C9 C10 C12 O14 -5.23(18) . . . . ? C11 C10 C12 O14 174.25(12) . . . . ? O13 C12 O14 C15 -0.4(2) . . . . ? C10 C12 O14 C15 -179.73(11) . . . . ? C12 O14 C15 C16 -176.80(12) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.24 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.201 _refine_diff_density_min -0.178 _refine_diff_density_rms 0.039