# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2010 data_global _journal_name_full 'New J.Chem.' _journal_coden_Cambridge 0440 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name _publ_author_address M.Barys ; Faculty of Chemistry University of Wroc\/law 14 Joliot-Curie St. Wroc\/law 50-383 Poland ; Z.Ciunik ; Faculty of Chemistry University of Wroc\/law 14 Joliot-Curie St. Wroc\/law 50-383 Poland ; K.Drabent ; Faculty of Chemistry University of Wroc\/law 14 Joliot-Curie St. Wroc\/law 50-383 Poland ; A.Kwiecien ; Faculty of Chemistry University of Wroc\/law 14 Joliot-Curie St. Wroc\/law 50-383 Poland ; _publ_contact_author_name 'Ciunik, Zbigniew' _publ_contact_author_email ciunik@wchuwr.pl _publ_section_title ; Stable hemiaminals containing a triazole ring ; _publ_contact_author_address ; Faculty of Chemistry University of Wroc\/law 14 Joliot-Curie St 50-383 Wroc\/law Poland ; _publ_contact_author_fax ? _publ_contact_author_phone 48713757240 # Attachment '- 17.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 751216' #TrackingRef '- 17.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (2-nitrophenyl)(4H-1,2,4-triazole-4-ylamino)methanol ; _chemical_name_common (2-nitrophenyl)(4H-1,2,4-triazole-4-ylamino)methanol _chemical_melting_point ? _chemical_formula_moiety 'C9 H9 N5 O3' _chemical_formula_sum 'C9 H9 N5 O3' _chemical_formula_weight 235.21 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' 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 P21/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.591(4) _cell_length_b 10.437(4) _cell_length_c 8.892(3) _cell_angle_alpha 90.00 _cell_angle_beta 105.27(2) _cell_angle_gamma 90.00 _cell_volume 1037.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2995 _cell_measurement_theta_min 3.24 _cell_measurement_theta_max 30.00 _exptl_crystal_description plates _exptl_crystal_colour yellow _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.506 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.117 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 KM4-CCD _diffrn_measurement_method /w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13472 _diffrn_reflns_av_R_equivalents 0.0976 _diffrn_reflns_av_sigmaI/netI 0.1046 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.24 _diffrn_reflns_theta_max 30.00 _reflns_number_total 2995 _reflns_number_gt 2067 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.0588P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2995 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1246 _refine_ls_R_factor_gt 0.0689 _refine_ls_wR_factor_ref 0.1450 _refine_ls_wR_factor_gt 0.1275 _refine_ls_goodness_of_fit_ref 1.188 _refine_ls_restrained_S_all 1.188 _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 O1 O 0.57788(15) 0.00362(15) 0.6647(2) 0.0569(5) Uani 1 1 d . . . O2 O 0.45580(17) 0.15069(19) 0.6857(3) 0.0922(7) Uani 1 1 d . . . O14 O 0.84523(13) 0.04740(13) 0.44265(16) 0.0376(4) Uani 1 1 d . . . N1 N 0.94422(16) -0.30810(15) 0.7133(2) 0.0428(4) Uani 1 1 d . . . N2 N 0.84649(16) -0.32142(15) 0.7747(2) 0.0440(5) Uani 1 1 d . . . N3 N 0.86181(13) -0.12066(13) 0.71656(17) 0.0299(4) Uani 1 1 d . . . N4 N 0.83432(15) 0.01134(13) 0.70396(19) 0.0305(4) Uani 1 1 d . . . H40 H 0.9015(19) 0.0517(18) 0.729(2) 0.029(5) Uiso 1 1 d . . . N5 N 0.54881(16) 0.11582(18) 0.6574(2) 0.0468(5) Uani 1 1 d . . . H41 H 0.836(3) -0.027(3) 0.387(3) 0.074(8) Uiso 1 1 d . . . C1 C 0.72339(16) 0.18226(16) 0.5565(2) 0.0283(4) Uani 1 1 d . . . C2 C 0.62446(17) 0.21430(18) 0.6114(2) 0.0333(4) Uani 1 1 d . . . C3 C 0.5911(2) 0.3400(2) 0.6265(3) 0.0441(5) Uani 1 1 d . . . H3 H 0.523(2) 0.354(2) 0.671(3) 0.058(7) Uiso 1 1 d . . . C4 C 0.6569(2) 0.4384(2) 0.5888(3) 0.0469(6) Uani 1 1 d . . . H4 H 0.635(2) 0.529(3) 0.600(3) 0.069(8) Uiso 1 1 d . . . C5 C 0.7542(2) 0.41064(19) 0.5336(3) 0.0445(5) Uani 1 1 d . . . H5 H 0.799(2) 0.476(2) 0.507(3) 0.050(6) Uiso 1 1 d . . . C6 C 0.7861(2) 0.28485(18) 0.5163(2) 0.0369(5) Uani 1 1 d . . . H6 H 0.853(2) 0.265(2) 0.476(2) 0.044(6) Uiso 1 1 d . . . C14 C 0.77014(17) 0.04720(16) 0.5440(2) 0.0285(4) Uani 1 1 d . . . H14 H 0.7040(17) -0.0140(17) 0.508(2) 0.025(5) Uiso 1 1 d . . . C1T C 0.94990(18) -0.18720(18) 0.6785(3) 0.0377(5) Uani 1 1 d . . . H1T H 1.007(2) -0.152(2) 0.638(3) 0.052(7) Uiso 1 1 d . . . C2T C 0.8002(2) -0.20838(19) 0.7756(3) 0.0421(5) Uani 1 1 d . . . H2T H 0.731(2) -0.189(2) 0.805(3) 0.054(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0520(10) 0.0505(10) 0.0763(12) 0.0074(8) 0.0313(9) -0.0077(8) O2 0.0629(12) 0.0808(13) 0.159(2) -0.0230(13) 0.0754(14) -0.0067(10) O14 0.0505(8) 0.0290(7) 0.0417(8) -0.0065(6) 0.0273(7) -0.0034(6) N1 0.0444(10) 0.0277(8) 0.0592(12) 0.0080(7) 0.0191(8) 0.0064(7) N2 0.0504(11) 0.0278(8) 0.0585(12) 0.0102(8) 0.0227(9) -0.0004(7) N3 0.0331(8) 0.0211(7) 0.0380(9) 0.0025(6) 0.0138(7) -0.0002(6) N4 0.0350(9) 0.0193(7) 0.0377(9) 0.0005(6) 0.0108(7) -0.0017(7) N5 0.0343(9) 0.0560(12) 0.0548(12) -0.0095(9) 0.0200(9) -0.0060(8) C1 0.0327(9) 0.0262(9) 0.0268(9) 0.0006(7) 0.0092(7) 0.0016(7) C2 0.0298(9) 0.0374(10) 0.0324(10) -0.0017(8) 0.0077(8) 0.0016(8) C3 0.0378(11) 0.0472(12) 0.0473(13) -0.0072(9) 0.0112(10) 0.0131(10) C4 0.0588(14) 0.0319(11) 0.0489(13) -0.0012(9) 0.0121(11) 0.0161(10) C5 0.0654(15) 0.0266(10) 0.0450(13) 0.0045(8) 0.0209(11) 0.0022(10) C6 0.0469(12) 0.0289(9) 0.0405(11) 0.0027(8) 0.0213(9) 0.0037(8) C14 0.0329(10) 0.0225(8) 0.0339(10) -0.0001(7) 0.0153(8) -0.0024(7) C1T 0.0353(11) 0.0296(10) 0.0528(13) 0.0079(9) 0.0195(9) 0.0051(8) C2T 0.0484(12) 0.0293(10) 0.0563(14) 0.0087(9) 0.0273(11) -0.0003(9) _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 N5 1.216(2) . ? O2 N5 1.225(2) . ? O14 C14 1.408(2) . ? O14 H41 0.92(3) . ? N1 C1T 1.305(2) . ? N1 N2 1.388(2) . ? N2 C2T 1.297(3) . ? N3 C2T 1.349(2) . ? N3 C1T 1.350(2) . ? N3 N4 1.412(2) . ? N4 C14 1.469(2) . ? N4 H40 0.86(2) . ? N5 C2 1.477(3) . ? C1 C6 1.392(3) . ? C1 C2 1.400(3) . ? C1 C14 1.525(2) . ? C2 C3 1.384(3) . ? C3 C4 1.371(3) . ? C3 H3 0.99(2) . ? C4 C5 1.374(3) . ? C4 H4 0.99(3) . ? C5 C6 1.383(3) . ? C5 H5 0.93(2) . ? C6 H6 0.96(2) . ? C14 H14 0.985(19) . ? C1T H1T 0.91(2) . ? C2T H2T 0.93(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C14 O14 H41 110.2(17) . . ? C1T N1 N2 106.72(15) . . ? C2T N2 N1 107.03(15) . . ? C2T N3 C1T 105.14(16) . . ? C2T N3 N4 124.15(16) . . ? C1T N3 N4 130.70(15) . . ? N3 N4 C14 111.81(13) . . ? N3 N4 H40 106.7(12) . . ? C14 N4 H40 108.3(13) . . ? O1 N5 O2 121.44(19) . . ? O1 N5 C2 120.59(16) . . ? O2 N5 C2 117.96(19) . . ? C6 C1 C2 115.88(16) . . ? C6 C1 C14 118.23(16) . . ? C2 C1 C14 125.83(16) . . ? C3 C2 C1 122.35(18) . . ? C3 C2 N5 115.58(17) . . ? C1 C2 N5 122.07(16) . . ? C4 C3 C2 119.9(2) . . ? C4 C3 H3 122.8(13) . . ? C2 C3 H3 117.1(14) . . ? C3 C4 C5 119.38(19) . . ? C3 C4 H4 121.1(16) . . ? C5 C4 H4 119.5(16) . . ? C4 C5 C6 120.5(2) . . ? C4 C5 H5 120.2(14) . . ? C6 C5 H5 119.2(14) . . ? C5 C6 C1 121.92(19) . . ? C5 C6 H6 121.0(13) . . ? C1 C6 H6 117.1(12) . . ? O14 C14 N4 112.29(15) . . ? O14 C14 C1 109.66(13) . . ? N4 C14 C1 105.33(14) . . ? O14 C14 H14 110.6(11) . . ? N4 C14 H14 107.6(11) . . ? C1 C14 H14 111.3(10) . . ? N1 C1T N3 110.43(17) . . ? N1 C1T H1T 124.5(14) . . ? N3 C1T H1T 125.0(14) . . ? N2 C2T N3 110.66(18) . . ? N2 C2T H2T 126.1(14) . . ? N3 C2T H2T 123.1(14) . . ? 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 C1T N1 N2 C2T -0.9(2) . . . . ? C2T N3 N4 C14 -101.7(2) . . . . ? C1T N3 N4 C14 79.3(2) . . . . ? C6 C1 C2 C3 -0.5(3) . . . . ? C14 C1 C2 C3 176.69(18) . . . . ? C6 C1 C2 N5 179.56(17) . . . . ? C14 C1 C2 N5 -3.2(3) . . . . ? O1 N5 C2 C3 -171.9(2) . . . . ? O2 N5 C2 C3 9.0(3) . . . . ? O1 N5 C2 C1 8.0(3) . . . . ? O2 N5 C2 C1 -171.1(2) . . . . ? C1 C2 C3 C4 -0.9(3) . . . . ? N5 C2 C3 C4 179.05(19) . . . . ? C2 C3 C4 C5 1.2(3) . . . . ? C3 C4 C5 C6 -0.2(3) . . . . ? C4 C5 C6 C1 -1.3(3) . . . . ? C2 C1 C6 C5 1.6(3) . . . . ? C14 C1 C6 C5 -175.84(19) . . . . ? N3 N4 C14 O14 -72.85(18) . . . . ? N3 N4 C14 C1 167.86(14) . . . . ? C6 C1 C14 O14 -20.6(2) . . . . ? C2 C1 C14 O14 162.23(17) . . . . ? C6 C1 C14 N4 100.41(18) . . . . ? C2 C1 C14 N4 -76.7(2) . . . . ? N2 N1 C1T N3 1.0(2) . . . . ? C2T N3 C1T N1 -0.7(2) . . . . ? N4 N3 C1T N1 178.41(18) . . . . ? N1 N2 C2T N3 0.5(2) . . . . ? C1T N3 C2T N2 0.1(2) . . . . ? N4 N3 C2T N2 -179.10(17) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.327 _refine_diff_density_min -0.283 _refine_diff_density_rms 0.069 data_2 _database_code_depnum_ccdc_archive 'CCDC 751217' #TrackingRef '- 17.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (3-nitrophenyl)(4H-1,2,4-triazole-4-ylamino)methanol ; _chemical_name_common (3-nitrophenyl)(4H-1,2,4-triazole-4-ylamino)methanol _chemical_melting_point ? _chemical_formula_moiety 'C9 H9 N5 O3' _chemical_formula_sum 'C9 H9 N5 O3' _chemical_formula_weight 235.21 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' 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.316(4) _cell_length_b 10.616(3) _cell_length_c 7.863(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.39(3) _cell_angle_gamma 90.00 _cell_volume 1027.2(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2988 _cell_measurement_theta_min 3.23 _cell_measurement_theta_max 30 _exptl_crystal_description plates _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.521 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.119 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 KM4-CCD _diffrn_measurement_method /w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15102 _diffrn_reflns_av_R_equivalents 0.0527 _diffrn_reflns_av_sigmaI/netI 0.0379 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.23 _diffrn_reflns_theta_max 30.00 _reflns_number_total 2988 _reflns_number_gt 2392 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.0708P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2988 _refine_ls_number_parameters 162 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0692 _refine_ls_R_factor_gt 0.0482 _refine_ls_wR_factor_ref 0.1232 _refine_ls_wR_factor_gt 0.1149 _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_restrained_S_all 1.099 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 1.06953(8) 0.85344(10) 0.45265(15) 0.0336(3) Uani 1 1 d . . . O2 O 1.07517(8) 0.64992(10) 0.46908(15) 0.0327(3) Uani 1 1 d . . . O14 O 0.64375(7) 0.94959(9) 0.00410(12) 0.0188(2) Uani 1 1 d . . . H41 H 0.6440(16) 1.024(2) -0.057(3) 0.051(6) Uiso 1 1 d . . . N1 N 0.54120(8) 1.30921(11) 0.22130(14) 0.0200(2) Uani 1 1 d . . . N2 N 0.63538(9) 1.33550(10) 0.31902(15) 0.0219(3) Uani 1 1 d . . . N3 N 0.62417(8) 1.13140(10) 0.28650(13) 0.0167(2) Uani 1 1 d . . . N4 N 0.65672(9) 1.00373(10) 0.29991(13) 0.0167(2) Uani 1 1 d . . . H40 H 0.5943(14) 0.9561(16) 0.305(2) 0.031(4) Uiso 1 1 d . . . N5 N 1.03076(9) 0.74870(11) 0.42108(16) 0.0214(3) Uani 1 1 d . . . C1 C 0.77397(9) 0.84393(11) 0.18968(15) 0.0144(2) Uani 1 1 d . . . C2 C 0.87251(9) 0.85123(12) 0.28281(16) 0.0159(3) Uani 1 1 d . . . H2 H 0.9017 0.9304 0.3178 0.019 Uiso 1 1 calc R . . C3 C 0.92701(10) 0.74022(12) 0.32316(16) 0.0167(3) Uani 1 1 d . . . C4 C 0.88730(10) 0.62231(12) 0.27657(16) 0.0195(3) Uani 1 1 d . . . H4 H 0.9259 0.5478 0.3081 0.023 Uiso 1 1 calc R . . C5 C 0.78968(10) 0.61653(12) 0.18275(16) 0.0195(3) Uani 1 1 d . . . H5 H 0.7609 0.5371 0.1479 0.023 Uiso 1 1 calc R . . C6 C 0.73337(10) 0.72684(11) 0.13910(16) 0.0168(3) Uani 1 1 d . . . H6 H 0.6667 0.7219 0.0742 0.020 Uiso 1 1 calc R . . C14 C 0.71417(10) 0.96554(11) 0.14691(16) 0.0149(2) Uani 1 1 d . . . H14 H 0.7687 1.0319 0.1210 0.018 Uiso 1 1 calc R . . C1T C 0.53767(10) 1.18661(12) 0.20237(17) 0.0191(3) Uani 1 1 d . . . H1T H 0.4825 1.1424 0.1389 0.023 Uiso 1 1 calc R . . C2T C 0.68258(11) 1.22770(12) 0.35681(18) 0.0210(3) Uani 1 1 d . . . H2T H 0.7481 1.2185 0.4237 0.025 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 O1 0.0233(5) 0.0281(6) 0.0481(7) 0.0027(5) -0.0133(5) -0.0020(4) O2 0.0245(5) 0.0297(6) 0.0432(7) 0.0061(5) -0.0085(5) 0.0117(4) O14 0.0231(5) 0.0156(5) 0.0170(4) 0.0020(3) -0.0064(4) -0.0012(4) N1 0.0186(5) 0.0185(6) 0.0225(6) -0.0047(4) -0.0033(4) 0.0024(4) N2 0.0207(5) 0.0189(6) 0.0258(6) -0.0061(4) -0.0038(5) 0.0009(4) N3 0.0167(5) 0.0147(5) 0.0184(5) -0.0022(4) -0.0028(4) 0.0017(4) N4 0.0187(5) 0.0130(5) 0.0183(5) -0.0002(4) -0.0011(4) 0.0021(4) N5 0.0163(5) 0.0238(6) 0.0241(6) 0.0024(4) -0.0005(4) 0.0040(4) C1 0.0149(5) 0.0143(6) 0.0141(6) 0.0011(4) 0.0020(4) 0.0009(4) C2 0.0153(6) 0.0143(6) 0.0181(6) 0.0003(4) 0.0010(5) 0.0008(4) C3 0.0137(5) 0.0204(6) 0.0159(6) 0.0011(5) 0.0004(4) 0.0022(5) C4 0.0222(6) 0.0161(6) 0.0204(6) 0.0027(5) 0.0038(5) 0.0055(5) C5 0.0234(6) 0.0142(6) 0.0210(6) -0.0019(5) 0.0019(5) -0.0006(5) C6 0.0173(6) 0.0167(6) 0.0163(6) 0.0007(5) 0.0004(5) -0.0006(5) C14 0.0146(5) 0.0135(6) 0.0163(6) -0.0002(4) -0.0026(4) -0.0008(4) C1T 0.0155(6) 0.0190(6) 0.0224(6) -0.0035(5) -0.0040(5) 0.0024(5) C2T 0.0193(6) 0.0187(6) 0.0243(7) -0.0057(5) -0.0068(5) 0.0005(5) _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 N5 1.2314(16) . ? O2 N5 1.2345(15) . ? O14 C14 1.4002(15) . ? O14 H41 0.92(2) . ? N1 C1T 1.3105(18) . ? N1 N2 1.3926(16) . ? N2 C2T 1.3121(17) . ? N3 C2T 1.3547(17) . ? N3 C1T 1.3628(16) . ? N3 N4 1.4161(15) . ? N4 C14 1.4776(17) . ? N4 H40 0.923(17) . ? N5 C3 1.4668(18) . ? C1 C6 1.3916(17) . ? C1 C2 1.3932(17) . ? C1 C14 1.5171(16) . ? C2 C3 1.3865(17) . ? C2 H2 0.9500 . ? C3 C4 1.3875(18) . ? C4 C5 1.3855(18) . ? C4 H4 0.9500 . ? C5 C6 1.3965(18) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C14 H14 1.0000 . ? C1T H1T 0.9500 . ? C2T H2T 0.9500 . ? 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 C14 O14 H41 107.2(13) . . ? C1T N1 N2 106.54(10) . . ? C2T N2 N1 107.52(10) . . ? C2T N3 C1T 105.34(11) . . ? C2T N3 N4 123.23(11) . . ? C1T N3 N4 131.37(10) . . ? N3 N4 C14 110.22(9) . . ? N3 N4 H40 107.1(10) . . ? C14 N4 H40 108.4(11) . . ? O1 N5 O2 122.83(13) . . ? O1 N5 C3 118.90(11) . . ? O2 N5 C3 118.26(11) . . ? C6 C1 C2 119.65(11) . . ? C6 C1 C14 122.10(11) . . ? C2 C1 C14 118.25(11) . . ? C3 C2 C1 118.41(11) . . ? C3 C2 H2 120.8 . . ? C1 C2 H2 120.8 . . ? C2 C3 C4 122.99(12) . . ? C2 C3 N5 118.08(11) . . ? C4 C3 N5 118.93(11) . . ? C5 C4 C3 117.97(11) . . ? C5 C4 H4 121.0 . . ? C3 C4 H4 121.0 . . ? C4 C5 C6 120.32(12) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C1 C6 C5 120.66(12) . . ? C1 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? O14 C14 N4 112.62(10) . . ? O14 C14 C1 110.71(10) . . ? N4 C14 C1 107.30(10) . . ? O14 C14 H14 108.7 . . ? N4 C14 H14 108.7 . . ? C1 C14 H14 108.7 . . ? N1 C1T N3 110.51(11) . . ? N1 C1T H1T 124.7 . . ? N3 C1T H1T 124.7 . . ? N2 C2T N3 110.07(12) . . ? N2 C2T H2T 125.0 . . ? N3 C2T H2T 125.0 . . ? 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 C1T N1 N2 C2T -1.23(14) . . . . ? C2T N3 N4 C14 -96.27(14) . . . . ? C1T N3 N4 C14 80.64(16) . . . . ? C6 C1 C2 C3 -0.37(18) . . . . ? C14 C1 C2 C3 179.56(11) . . . . ? C1 C2 C3 C4 -0.71(19) . . . . ? C1 C2 C3 N5 179.94(11) . . . . ? O1 N5 C3 C2 -5.40(19) . . . . ? O2 N5 C3 C2 174.23(11) . . . . ? O1 N5 C3 C4 175.22(11) . . . . ? O2 N5 C3 C4 -5.14(18) . . . . ? C2 C3 C4 C5 1.25(19) . . . . ? N5 C3 C4 C5 -179.40(11) . . . . ? C3 C4 C5 C6 -0.71(18) . . . . ? C2 C1 C6 C5 0.88(18) . . . . ? C14 C1 C6 C5 -179.05(11) . . . . ? C4 C5 C6 C1 -0.33(19) . . . . ? N3 N4 C14 O14 -73.86(12) . . . . ? N3 N4 C14 C1 164.07(9) . . . . ? C6 C1 C14 O14 -23.20(16) . . . . ? C2 C1 C14 O14 156.87(11) . . . . ? C6 C1 C14 N4 100.05(13) . . . . ? C2 C1 C14 N4 -79.88(13) . . . . ? N2 N1 C1T N3 1.31(14) . . . . ? C2T N3 C1T N1 -0.90(14) . . . . ? N4 N3 C1T N1 -178.22(11) . . . . ? N1 N2 C2T N3 0.70(15) . . . . ? C1T N3 C2T N2 0.08(15) . . . . ? N4 N3 C2T N2 177.68(11) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.474 _refine_diff_density_min -0.236 _refine_diff_density_rms 0.061 # start Validation Reply Form _vrf_PLAT112_2 ; PROBLEM: ADDSYM Detects Additional (Pseudo) Symm. Elem... Z RESPONSE: The pseudo translation suggested by PLATON was checked and there is no additional symmetry in the crystal structure. Obtained results showed that after translation it was possible to overlay aromatic rings (phenyl and triazole, respectively), but not the atomic linkage between these rings. ; data_3 _database_code_depnum_ccdc_archive 'CCDC 751218' #TrackingRef '- 17.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (4-nitrophenyl)(4H-1,2,4-triazole-4-ylamino)methanol ; _chemical_name_common (4-nitrophenyl)(4H-1,2,4-triazole-4-ylamino)methanol _chemical_melting_point ? _chemical_formula_moiety 'C9 H9 N5 O3' _chemical_formula_sum 'C9 H9 N5 O3' _chemical_formula_weight 235.21 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M Cc _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' _cell_length_a 6.948(3) _cell_length_b 20.546(6) _cell_length_c 7.362(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.56(3) _cell_angle_gamma 90.00 _cell_volume 1048.9(7) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1791 _cell_measurement_theta_min 4.84 _cell_measurement_theta_max 31.99 _exptl_crystal_description needles _exptl_crystal_colour yellow _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.489 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.116 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Xcalibur PX with Onyx CCD' _diffrn_measurement_method '/phi & /w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6722 _diffrn_reflns_av_R_equivalents 0.0210 _diffrn_reflns_av_sigmaI/netI 0.0199 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 4.84 _diffrn_reflns_theta_max 31.99 _reflns_number_total 1791 _reflns_number_gt 1674 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.0628P)^2^+0.0453P] 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 1791 _refine_ls_number_parameters 162 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0361 _refine_ls_R_factor_gt 0.0328 _refine_ls_wR_factor_ref 0.0870 _refine_ls_wR_factor_gt 0.0851 _refine_ls_goodness_of_fit_ref 1.058 _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 O1 O -0.0493(3) -0.11226(7) 0.9680(2) 0.0398(4) Uani 1 1 d . . . O2 O -0.2454(2) -0.03966(8) 1.0613(2) 0.0379(4) Uani 1 1 d . . . O14 O 0.33801(17) 0.19608(6) 0.73923(15) 0.0190(2) Uani 1 1 d . . . H41 H 0.368(5) 0.2015(14) 0.629(5) 0.043(8) Uiso 1 1 d . . . N1 N 0.4341(2) 0.19931(7) 1.38242(18) 0.0210(3) Uani 1 1 d . . . N2 N 0.35525(19) 0.25084(7) 1.28097(17) 0.0189(3) Uani 1 1 d . . . N3 N 0.50814(17) 0.18686(6) 1.10075(16) 0.0136(2) Uani 1 1 d . . . N4 N 0.58847(17) 0.15755(6) 0.94959(17) 0.0154(2) Uani 1 1 d . . . H40 H 0.664(4) 0.1874(11) 0.906(3) 0.023(6) Uiso 1 1 d . . . N5 N -0.0911(2) -0.05597(8) 1.0013(2) 0.0269(3) Uani 1 1 d . . . C1 C 0.3034(2) 0.09022(7) 0.87165(18) 0.0145(3) Uani 1 1 d . . . C2 C 0.3601(2) 0.02467(7) 0.8759(2) 0.0179(3) Uani 1 1 d . . . H2 H 0.4874 0.0132 0.8478 0.021 Uiso 1 1 calc R . . C3 C 0.2321(2) -0.02334(7) 0.9206(2) 0.0198(3) Uani 1 1 d . . . H3 H 0.2687 -0.0679 0.9213 0.024 Uiso 1 1 calc R . . C4 C 0.0491(2) -0.00481(8) 0.9644(2) 0.0185(3) Uani 1 1 d . . . C5 C -0.0100(2) 0.05950(8) 0.9680(2) 0.0204(3) Uani 1 1 d . . . H5 H -0.1350 0.0708 1.0031 0.025 Uiso 1 1 calc R . . C6 C 0.1189(2) 0.10714(7) 0.9188(2) 0.0184(3) Uani 1 1 d . . . H6 H 0.0810 0.1516 0.9174 0.022 Uiso 1 1 calc R . . C14 C 0.4405(2) 0.14119(7) 0.80597(19) 0.0152(2) Uani 1 1 d . . . H14 H 0.5075 0.1219 0.7024 0.018 Uiso 1 1 calc R . . C1T C 0.5244(2) 0.16209(8) 1.2713(2) 0.0194(3) Uani 1 1 d . . . H1T H 0.5916 0.1233 1.3054 0.023 Uiso 1 1 calc R . . C2T C 0.4021(2) 0.24252(7) 1.1128(2) 0.0175(3) Uani 1 1 d . . . H2T H 0.3676 0.2709 1.0142 0.021 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 O1 0.0443(9) 0.0212(6) 0.0528(9) 0.0061(6) -0.0067(7) -0.0119(6) O2 0.0199(6) 0.0411(7) 0.0524(10) 0.0210(7) 0.0005(6) -0.0065(6) O14 0.0223(6) 0.0204(5) 0.0147(5) 0.0038(4) 0.0043(4) 0.0043(4) N1 0.0238(6) 0.0247(6) 0.0146(6) 0.0022(5) 0.0026(5) 0.0024(5) N2 0.0208(6) 0.0200(6) 0.0161(6) 0.0000(4) 0.0044(5) 0.0026(5) N3 0.0133(5) 0.0144(5) 0.0133(5) 0.0008(4) 0.0031(4) 0.0009(4) N4 0.0130(5) 0.0185(5) 0.0153(5) -0.0005(4) 0.0053(4) 0.0003(4) N5 0.0223(7) 0.0278(7) 0.0294(7) 0.0117(6) -0.0089(5) -0.0078(5) C1 0.0151(6) 0.0147(6) 0.0137(5) -0.0008(4) 0.0016(5) 0.0005(4) C2 0.0171(7) 0.0170(6) 0.0196(6) -0.0005(5) 0.0012(5) 0.0024(5) C3 0.0215(7) 0.0155(6) 0.0219(7) 0.0014(5) -0.0030(5) -0.0004(5) C4 0.0177(7) 0.0175(6) 0.0197(6) 0.0041(5) -0.0030(5) -0.0049(5) C5 0.0151(6) 0.0215(7) 0.0248(7) 0.0038(5) 0.0025(5) 0.0010(5) C6 0.0174(7) 0.0155(6) 0.0226(7) 0.0015(5) 0.0039(5) 0.0017(5) C14 0.0164(6) 0.0162(6) 0.0133(5) -0.0002(5) 0.0045(4) 0.0009(5) C1T 0.0200(7) 0.0233(7) 0.0151(6) 0.0047(5) 0.0023(5) 0.0034(6) C2T 0.0226(7) 0.0140(6) 0.0160(6) 0.0002(5) 0.0027(5) 0.0022(5) _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 N5 1.221(2) . ? O2 N5 1.231(2) . ? O14 C14 1.4059(18) . ? O14 H41 0.86(3) . ? N1 C1T 1.308(2) . ? N1 N2 1.388(2) . ? N2 C2T 1.3108(19) . ? N3 C1T 1.3531(18) . ? N3 C2T 1.3661(19) . ? N3 N4 1.4106(17) . ? N4 C14 1.467(2) . ? N4 H40 0.88(2) . ? N5 C4 1.470(2) . ? C1 C6 1.393(2) . ? C1 C2 1.403(2) . ? C1 C14 1.515(2) . ? C2 C3 1.382(2) . ? C2 H2 0.9500 . ? C3 C4 1.385(2) . ? C3 H3 0.9500 . ? C4 C5 1.384(2) . ? C5 C6 1.390(2) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C14 H14 1.0000 . ? C1T H1T 0.9500 . ? C2T H2T 0.9500 . ? 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 C14 O14 H41 107(2) . . ? C1T N1 N2 107.33(13) . . ? C2T N2 N1 107.21(13) . . ? C1T N3 C2T 105.59(12) . . ? C1T N3 N4 123.87(12) . . ? C2T N3 N4 130.54(12) . . ? N3 N4 C14 111.86(11) . . ? N3 N4 H40 105.2(15) . . ? C14 N4 H40 107.9(16) . . ? O1 N5 O2 123.58(16) . . ? O1 N5 C4 118.16(17) . . ? O2 N5 C4 118.26(16) . . ? C6 C1 C2 119.70(13) . . ? C6 C1 C14 120.89(13) . . ? C2 C1 C14 119.32(13) . . ? C3 C2 C1 120.45(15) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C2 C3 C4 118.24(14) . . ? C2 C3 H3 120.9 . . ? C4 C3 H3 120.9 . . ? C5 C4 C3 123.01(14) . . ? C5 C4 N5 118.58(15) . . ? C3 C4 N5 118.36(14) . . ? C4 C5 C6 118.06(14) . . ? C4 C5 H5 121.0 . . ? C6 C5 H5 121.0 . . ? C5 C6 C1 120.48(14) . . ? C5 C6 H6 119.8 . . ? C1 C6 H6 119.8 . . ? O14 C14 N4 112.65(12) . . ? O14 C14 C1 110.59(12) . . ? N4 C14 C1 110.77(11) . . ? O14 C14 H14 107.5 . . ? N4 C14 H14 107.5 . . ? C1 C14 H14 107.5 . . ? N1 C1T N3 110.18(14) . . ? N1 C1T H1T 124.9 . . ? N3 C1T H1T 124.9 . . ? N2 C2T N3 109.70(13) . . ? N2 C2T H2T 125.2 . . ? N3 C2T H2T 125.2 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1T N1 N2 C2T -0.21(17) . . . . ? C1T N3 N4 C14 120.34(15) . . . . ? C2T N3 N4 C14 -59.29(19) . . . . ? C6 C1 C2 C3 2.2(2) . . . . ? C14 C1 C2 C3 -174.57(13) . . . . ? C1 C2 C3 C4 -1.3(2) . . . . ? C2 C3 C4 C5 -1.0(2) . . . . ? C2 C3 C4 N5 176.38(14) . . . . ? O1 N5 C4 C5 167.82(16) . . . . ? O2 N5 C4 C5 -11.1(2) . . . . ? O1 N5 C4 C3 -9.7(2) . . . . ? O2 N5 C4 C3 171.38(15) . . . . ? C3 C4 C5 C6 2.4(2) . . . . ? N5 C4 C5 C6 -175.00(14) . . . . ? C4 C5 C6 C1 -1.5(2) . . . . ? C2 C1 C6 C5 -0.8(2) . . . . ? C14 C1 C6 C5 175.94(14) . . . . ? N3 N4 C14 O14 60.12(15) . . . . ? N3 N4 C14 C1 -64.33(15) . . . . ? C6 C1 C14 O14 -21.50(18) . . . . ? C2 C1 C14 O14 155.20(12) . . . . ? C6 C1 C14 N4 104.12(15) . . . . ? C2 C1 C14 N4 -79.18(16) . . . . ? N2 N1 C1T N3 -0.08(18) . . . . ? C2T N3 C1T N1 0.33(17) . . . . ? N4 N3 C1T N1 -179.39(13) . . . . ? N1 N2 C2T N3 0.42(17) . . . . ? C1T N3 C2T N2 -0.46(17) . . . . ? N4 N3 C2T N2 179.22(14) . . . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.359 _refine_diff_density_min -0.212 _refine_diff_density_rms 0.049 data_4 _database_code_depnum_ccdc_archive 'CCDC 751219' #TrackingRef '- 17.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (2,4-dinitrophenyl)(4H-1,2,4-triazole-4-ylamino)methanol ; _chemical_name_common (2,4-dinitrophenyl)(4H-1,2,4-triazole-4-ylamino)methanol _chemical_melting_point ? _chemical_formula_moiety 'C9 H8 N6 O5' _chemical_formula_sum 'C9 H8 N6 O5' _chemical_formula_weight 280.21 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pccn _symmetry_space_group_name_Hall '-P 2ab 2ac' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-x, y+1/2, -z+1/2' 'x+1/2, -y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'x, -y-1/2, z-1/2' '-x-1/2, y, z-1/2' _cell_length_a 14.202(4) _cell_length_b 14.267(4) _cell_length_c 11.223(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2274.0(11) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3151 _cell_measurement_theta_min 3.63 _cell_measurement_theta_max 29.50 _exptl_crystal_description plates _exptl_crystal_colour yellow _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.637 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152 _exptl_absorpt_coefficient_mu 0.137 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 KM4-CCD _diffrn_measurement_method /w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26651 _diffrn_reflns_av_R_equivalents 0.0548 _diffrn_reflns_av_sigmaI/netI 0.0341 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.63 _diffrn_reflns_theta_max 29.50 _reflns_number_total 3151 _reflns_number_gt 2488 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.0556P)^2^+0.1991P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3151 _refine_ls_number_parameters 213 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0732 _refine_ls_R_factor_gt 0.0481 _refine_ls_wR_factor_ref 0.1141 _refine_ls_wR_factor_gt 0.1054 _refine_ls_goodness_of_fit_ref 1.161 _refine_ls_restrained_S_all 1.161 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 1.14379(9) 0.72510(9) 0.55948(10) 0.0328(3) Uani 1 1 d . . . O2 O 1.00662(8) 0.66815(9) 0.59966(10) 0.0298(3) Uani 1 1 d . . . O3 O 1.39538(9) 0.52877(10) 0.92636(11) 0.0377(3) Uani 1 1 d . . . O4 O 1.39874(8) 0.54872(9) 0.73485(11) 0.0320(3) Uani 1 1 d . . . O14 O 0.92580(8) 0.63629(7) 0.94944(9) 0.0228(2) Uani 1 1 d . . . H41 H 0.8621(17) 0.6255(17) 0.9296(18) 0.053(7) Uiso 1 1 d . . . N1 N 0.75648(9) 0.87426(9) 0.86945(12) 0.0245(3) Uani 1 1 d . . . N2 N 0.76778(9) 0.87451(9) 0.74570(12) 0.0265(3) Uani 1 1 d . . . N3 N 0.89400(9) 0.81447(9) 0.82821(11) 0.0202(3) Uani 1 1 d . . . N4 N 0.98169(9) 0.76813(9) 0.83418(12) 0.0204(3) Uani 1 1 d . . . H40 H 1.0076(13) 0.7865(14) 0.8974(19) 0.031(5) Uiso 1 1 d . . . N5 N 1.08929(9) 0.68280(9) 0.62458(11) 0.0226(3) Uani 1 1 d . . . N6 N 1.35840(9) 0.54943(9) 0.83097(12) 0.0252(3) Uani 1 1 d . . . C1 C 1.06884(10) 0.62705(10) 0.83507(13) 0.0183(3) Uani 1 1 d . . . C2 C 1.12691(10) 0.64300(10) 0.73626(13) 0.0188(3) Uani 1 1 d . . . C3 C 1.22155(11) 0.62028(10) 0.73388(13) 0.0203(3) Uani 1 1 d . . . H3 H 1.2579(12) 0.6335(12) 0.6679(15) 0.018(4) Uiso 1 1 d . . . C4 C 1.25833(10) 0.57728(10) 0.83346(13) 0.0202(3) Uani 1 1 d . . . C5 C 1.20428(11) 0.55685(11) 0.93209(14) 0.0214(3) Uani 1 1 d . . . H5 H 1.2288(12) 0.5252(12) 0.9984(15) 0.023(4) Uiso 1 1 d . . . C6 C 1.10988(11) 0.58279(10) 0.93246(13) 0.0206(3) Uani 1 1 d . . . H6 H 1.0680(12) 0.5699(12) 0.9983(15) 0.022(4) Uiso 1 1 d . . . C14 C 0.96914(10) 0.66522(10) 0.84350(13) 0.0191(3) Uani 1 1 d . . . H14 H 0.9321(12) 0.6487(11) 0.7788(16) 0.019(4) Uiso 1 1 d . . . C1T C 0.83244(11) 0.83728(11) 0.91523(14) 0.0241(3) Uani 1 1 d . . . H1T H 0.8441(14) 0.8277(13) 0.9982(18) 0.036(5) Uiso 1 1 d . . . C2T C 0.85099(12) 0.83934(11) 0.72495(15) 0.0253(3) Uani 1 1 d . . . H2T H 0.8747(14) 0.8315(14) 0.6506(17) 0.033(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0338(6) 0.0371(7) 0.0273(6) 0.0147(5) 0.0002(5) -0.0034(5) O2 0.0251(6) 0.0444(7) 0.0198(6) 0.0029(5) -0.0046(5) 0.0017(5) O3 0.0324(7) 0.0454(8) 0.0351(7) -0.0001(6) -0.0116(5) 0.0130(6) O4 0.0261(6) 0.0365(7) 0.0335(7) -0.0017(5) 0.0045(5) 0.0042(5) O14 0.0248(6) 0.0261(6) 0.0175(5) 0.0033(4) 0.0016(4) -0.0003(4) N1 0.0255(6) 0.0233(7) 0.0248(7) -0.0004(5) 0.0013(5) 0.0013(5) N2 0.0306(7) 0.0236(7) 0.0252(7) 0.0030(5) -0.0004(6) 0.0037(5) N3 0.0210(6) 0.0191(6) 0.0207(6) 0.0006(5) 0.0008(5) 0.0021(5) N4 0.0192(6) 0.0194(6) 0.0226(7) -0.0006(5) -0.0015(5) 0.0026(5) N5 0.0264(7) 0.0235(7) 0.0179(6) 0.0012(5) -0.0015(5) 0.0031(5) N6 0.0234(7) 0.0215(7) 0.0306(7) -0.0029(6) -0.0046(6) 0.0035(5) C1 0.0224(7) 0.0154(7) 0.0171(7) -0.0018(5) -0.0020(6) -0.0003(5) C2 0.0240(7) 0.0171(7) 0.0153(7) 0.0006(5) -0.0041(6) 0.0004(5) C3 0.0246(7) 0.0178(7) 0.0183(7) -0.0020(6) 0.0004(6) -0.0011(5) C4 0.0208(7) 0.0165(7) 0.0233(8) -0.0041(6) -0.0034(6) 0.0028(5) C5 0.0287(8) 0.0177(7) 0.0177(7) -0.0010(6) -0.0049(6) 0.0037(6) C6 0.0264(8) 0.0189(7) 0.0165(7) -0.0009(6) -0.0001(6) 0.0014(6) C14 0.0215(7) 0.0200(7) 0.0158(7) 0.0008(6) -0.0001(6) 0.0015(5) C1T 0.0255(8) 0.0251(8) 0.0216(8) -0.0013(6) 0.0019(6) 0.0018(6) C2T 0.0318(8) 0.0236(8) 0.0204(8) 0.0041(6) 0.0008(6) 0.0050(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 N5 1.2235(17) . ? O2 N5 1.2250(17) . ? O3 N6 1.2283(18) . ? O4 N6 1.2215(17) . ? O14 C14 1.4010(18) . ? O14 H41 0.94(2) . ? N1 C1T 1.306(2) . ? N1 N2 1.3980(19) . ? N2 C2T 1.305(2) . ? N3 C1T 1.351(2) . ? N3 C2T 1.357(2) . ? N3 N4 1.4117(17) . ? N4 C14 1.4826(19) . ? N4 H40 0.84(2) . ? N5 C2 1.4761(19) . ? N6 C4 1.476(2) . ? C1 C6 1.390(2) . ? C1 C2 1.401(2) . ? C1 C14 1.520(2) . ? C2 C3 1.383(2) . ? C3 C4 1.378(2) . ? C3 H3 0.922(17) . ? C4 C5 1.378(2) . ? C5 C6 1.391(2) . ? C5 H5 0.938(17) . ? C6 H6 0.966(17) . ? C14 H14 0.927(17) . ? C1T H1T 0.95(2) . ? C2T H2T 0.907(19) . ? 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 C14 O14 H41 105.6(13) . . ? C1T N1 N2 107.27(13) . . ? C2T N2 N1 106.28(13) . . ? C1T N3 C2T 105.26(13) . . ? C1T N3 N4 130.51(13) . . ? C2T N3 N4 124.06(13) . . ? N3 N4 C14 111.17(11) . . ? N3 N4 H40 106.3(13) . . ? C14 N4 H40 107.5(13) . . ? O1 N5 O2 123.66(13) . . ? O1 N5 C2 117.90(12) . . ? O2 N5 C2 118.36(12) . . ? O4 N6 O3 124.56(14) . . ? O4 N6 C4 118.07(13) . . ? O3 N6 C4 117.37(13) . . ? C6 C1 C2 116.70(13) . . ? C6 C1 C14 120.29(13) . . ? C2 C1 C14 122.66(13) . . ? C3 C2 C1 123.34(14) . . ? C3 C2 N5 115.18(13) . . ? C1 C2 N5 121.44(13) . . ? C4 C3 C2 117.20(14) . . ? C4 C3 H3 122.0(10) . . ? C2 C3 H3 120.8(10) . . ? C3 C4 C5 122.31(14) . . ? C3 C4 N6 118.01(13) . . ? C5 C4 N6 119.64(13) . . ? C4 C5 C6 118.88(14) . . ? C4 C5 H5 122.2(10) . . ? C6 C5 H5 118.9(10) . . ? C1 C6 C5 121.51(14) . . ? C1 C6 H6 115.5(10) . . ? C5 C6 H6 123.0(10) . . ? O14 C14 N4 113.86(12) . . ? O14 C14 C1 110.89(12) . . ? N4 C14 C1 103.79(11) . . ? O14 C14 H14 109.9(10) . . ? N4 C14 H14 105.3(10) . . ? C1 C14 H14 112.9(10) . . ? N1 C1T N3 110.33(14) . . ? N1 C1T H1T 125.7(12) . . ? N3 C1T H1T 123.9(12) . . ? N2 C2T N3 110.84(14) . . ? N2 C2T H2T 123.3(13) . . ? N3 C2T H2T 125.9(13) . . ? 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 C1T N1 N2 C2T -1.31(17) . . . . ? C1T N3 N4 C14 79.85(19) . . . . ? C2T N3 N4 C14 -94.67(17) . . . . ? C6 C1 C2 C3 -2.5(2) . . . . ? C14 C1 C2 C3 170.65(14) . . . . ? C6 C1 C2 N5 175.26(13) . . . . ? C14 C1 C2 N5 -11.6(2) . . . . ? O1 N5 C2 C3 -27.43(19) . . . . ? O2 N5 C2 C3 149.35(14) . . . . ? O1 N5 C2 C1 154.64(14) . . . . ? O2 N5 C2 C1 -28.6(2) . . . . ? C1 C2 C3 C4 2.0(2) . . . . ? N5 C2 C3 C4 -175.89(13) . . . . ? C2 C3 C4 C5 0.2(2) . . . . ? C2 C3 C4 N6 177.86(13) . . . . ? O4 N6 C4 C3 -14.0(2) . . . . ? O3 N6 C4 C3 165.78(14) . . . . ? O4 N6 C4 C5 163.70(14) . . . . ? O3 N6 C4 C5 -16.5(2) . . . . ? C3 C4 C5 C6 -1.8(2) . . . . ? N6 C4 C5 C6 -179.38(13) . . . . ? C2 C1 C6 C5 0.8(2) . . . . ? C14 C1 C6 C5 -172.50(14) . . . . ? C4 C5 C6 C1 1.2(2) . . . . ? N3 N4 C14 O14 -65.37(16) . . . . ? N3 N4 C14 C1 173.96(12) . . . . ? C6 C1 C14 O14 -9.13(19) . . . . ? C2 C1 C14 O14 177.95(13) . . . . ? C6 C1 C14 N4 113.52(15) . . . . ? C2 C1 C14 N4 -59.40(17) . . . . ? N2 N1 C1T N3 0.99(17) . . . . ? C2T N3 C1T N1 -0.30(18) . . . . ? N4 N3 C1T N1 -175.60(14) . . . . ? N1 N2 C2T N3 1.15(18) . . . . ? C1T N3 C2T N2 -0.57(18) . . . . ? N4 N3 C2T N2 175.12(13) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 29.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.348 _refine_diff_density_min -0.197 _refine_diff_density_rms 0.052 data_5 _database_code_depnum_ccdc_archive 'CCDC 751220' #TrackingRef '- 17.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (2-chloro-6-nitrophenyl)(4H-1,2,4-triazole-4-ylamino)methanol ; _chemical_name_common (2-chloro-6-nitrophenyl)(4H-1,2,4-triazole-4-ylamino)methanol _chemical_melting_point ? _chemical_formula_moiety 'C9 H8 Cl N5 O3' _chemical_formula_sum 'C9 H8 Cl N5 O3' _chemical_formula_weight 269.65 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.882(4) _cell_length_b 8.440(3) _cell_length_c 21.129(7) _cell_angle_alpha 90.00 _cell_angle_beta 100.04(3) _cell_angle_gamma 90.00 _cell_volume 2262.1(13) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6273 _cell_measurement_theta_min 2.90 _cell_measurement_theta_max 30.00 _exptl_crystal_description plates _exptl_crystal_colour yellow _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.584 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 0.347 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 KM4-CCD _diffrn_measurement_method /w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25378 _diffrn_reflns_av_R_equivalents 0.1096 _diffrn_reflns_av_sigmaI/netI 0.1725 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.90 _diffrn_reflns_theta_max 30.00 _reflns_number_total 6273 _reflns_number_gt 2957 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.0532P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6273 _refine_ls_number_parameters 335 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1898 _refine_ls_R_factor_gt 0.0789 _refine_ls_wR_factor_ref 0.1660 _refine_ls_wR_factor_gt 0.1421 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 ClA Cl 0.04377(10) 0.25303(16) 0.55898(6) 0.0442(3) Uani 1 1 d . . . O1A O 0.4548(2) 0.1030(4) 0.55912(14) 0.0353(8) Uani 1 1 d . . . O2A O 0.5228(3) 0.3290(4) 0.59329(16) 0.0488(9) Uani 1 1 d . . . O14A O 0.3271(2) 0.2804(3) 0.47300(13) 0.0290(7) Uani 1 1 d . . . H41A H 0.3058 0.3388 0.4412 0.044 Uiso 1 1 calc R . . N1A N 0.2498(3) -0.0639(4) 0.33250(15) 0.0284(9) Uani 1 1 d . . . N2A N 0.1416(3) -0.0394(4) 0.32438(17) 0.0385(10) Uani 1 1 d . . . N3A N 0.2119(3) 0.0122(4) 0.42391(14) 0.0207(8) Uani 1 1 d . . . N4A N 0.2213(3) 0.0538(4) 0.48937(15) 0.0239(8) Uani 1 1 d . . . H40A H 0.275(3) -0.009(5) 0.510(2) 0.026(12) Uiso 1 1 d . . . N5A N 0.4515(3) 0.2363(5) 0.58409(16) 0.0269(8) Uani 1 1 d . . . C1A C 0.2555(3) 0.2547(4) 0.57116(17) 0.0183(9) Uani 1 1 d . . . C2A C 0.1699(3) 0.2761(4) 0.60223(19) 0.0240(10) Uani 1 1 d . . . C3A C 0.1808(4) 0.3194(5) 0.66644(19) 0.0286(11) Uani 1 1 d . . . H3A H 0.1203 0.3345 0.6858 0.034 Uiso 1 1 calc R . . C4A C 0.2810(4) 0.3403(5) 0.70199(19) 0.0277(11) Uani 1 1 d . . . H4A H 0.2893 0.3713 0.7458 0.033 Uiso 1 1 calc R . . C5A C 0.3678(4) 0.3164(5) 0.67420(18) 0.0268(10) Uani 1 1 d . . . H5A H 0.4366 0.3295 0.6985 0.032 Uiso 1 1 calc R . . C6A C 0.3540(3) 0.2725(4) 0.60979(17) 0.0203(9) Uani 1 1 d . . . C14A C 0.2404(3) 0.2257(4) 0.49887(17) 0.0202(9) Uani 1 1 d . . . H14A H 0.1761 0.2842 0.4778 0.024 Uiso 1 1 calc R . . C1TA C 0.2890(4) -0.0305(5) 0.39161(19) 0.0266(10) Uani 1 1 d . . . H1TA H 0.3618 -0.0353 0.4097 0.032 Uiso 1 1 calc R . . C2TA C 0.1220(4) 0.0044(5) 0.3802(2) 0.0352(11) Uani 1 1 d . . . H2TA H 0.0538 0.0278 0.3890 0.042 Uiso 1 1 calc R . . ClB Cl 0.06830(9) 0.66758(13) 0.60368(5) 0.0302(3) Uani 1 1 d . . . O1B O 0.4506(2) 0.9541(3) 0.68628(13) 0.0343(8) Uani 1 1 d . . . O2B O 0.5472(3) 0.7576(4) 0.66653(15) 0.0450(9) Uani 1 1 d . . . O14B O 0.3461(2) 0.7340(3) 0.74748(12) 0.0250(7) Uani 1 1 d . . . H41B H 0.3284 0.6771 0.7764 0.037 Uiso 1 1 calc R . . N1B N 0.2346(3) 1.0603(4) 0.86602(16) 0.0311(9) Uani 1 1 d . . . N2B N 0.1274(3) 1.0680(5) 0.84289(17) 0.0403(10) Uani 1 1 d . . . N3B N 0.2075(3) 0.9846(4) 0.76620(14) 0.0222(8) Uani 1 1 d . . . N4B N 0.2236(3) 0.9410(4) 0.70387(15) 0.0246(9) Uani 1 1 d . . . H40B H 0.276(4) 0.997(5) 0.701(2) 0.032(14) Uiso 1 1 d . . . N5B N 0.4636(3) 0.8264(4) 0.66040(16) 0.0259(8) Uani 1 1 d . . . C1B C 0.2755(3) 0.7434(4) 0.63419(17) 0.0198(9) Uani 1 1 d . . . C2B C 0.1951(3) 0.6892(4) 0.58610(19) 0.0223(9) Uani 1 1 d . . . C3B C 0.2123(4) 0.6479(5) 0.52542(18) 0.0247(10) Uani 1 1 d . . . H3B H 0.1555 0.6102 0.4942 0.030 Uiso 1 1 calc R . . C4B C 0.3121(4) 0.6615(5) 0.51022(19) 0.0285(11) Uani 1 1 d . . . H4B H 0.3242 0.6318 0.4687 0.034 Uiso 1 1 calc R . . C5B C 0.3939(4) 0.7181(4) 0.55534(19) 0.0247(10) Uani 1 1 d . . . H5B H 0.4627 0.7289 0.5454 0.030 Uiso 1 1 calc R . . C6B C 0.3737(3) 0.7590(4) 0.61554(17) 0.0191(9) Uani 1 1 d . . . C14B C 0.2562(3) 0.7740(4) 0.70252(17) 0.0200(9) Uani 1 1 d . . . H14B H 0.1963 0.7057 0.7104 0.024 Uiso 1 1 calc R . . C1TB C 0.2806(4) 1.0097(5) 0.81946(19) 0.0282(10) Uani 1 1 d . . . H1TB H 0.3542 0.9931 0.8225 0.034 Uiso 1 1 calc R . . C2TB C 0.1133(4) 1.0217(5) 0.7827(2) 0.0340(11) Uani 1 1 d . . . H2TB H 0.0470 1.0150 0.7549 0.041 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 ClA 0.0308(8) 0.0630(8) 0.0386(7) -0.0028(6) 0.0052(6) 0.0015(6) O1A 0.043(2) 0.0375(18) 0.0278(17) 0.0039(14) 0.0119(16) 0.0110(15) O2A 0.045(2) 0.059(2) 0.047(2) -0.0069(18) 0.0177(19) -0.016(2) O14A 0.039(2) 0.0280(16) 0.0182(15) 0.0073(12) 0.0009(14) 0.0013(14) N1A 0.035(3) 0.032(2) 0.0182(19) -0.0036(15) 0.0058(17) 0.0027(18) N2A 0.042(3) 0.044(2) 0.028(2) -0.0117(17) 0.0046(19) -0.003(2) N3A 0.026(2) 0.0233(18) 0.0136(16) -0.0032(13) 0.0052(16) -0.0018(15) N4A 0.042(3) 0.0221(18) 0.0087(16) -0.0001(14) 0.0067(16) 0.0019(18) N5A 0.025(2) 0.035(2) 0.0192(18) -0.0026(16) -0.0006(16) 0.0061(18) C1A 0.029(3) 0.0122(18) 0.0135(18) 0.0004(15) 0.0035(18) 0.0022(18) C2A 0.024(3) 0.022(2) 0.027(2) -0.0019(17) 0.005(2) 0.0031(18) C3A 0.037(3) 0.028(2) 0.024(2) 0.0060(18) 0.013(2) 0.012(2) C4A 0.046(3) 0.025(2) 0.013(2) -0.0004(17) 0.006(2) 0.005(2) C5A 0.035(3) 0.027(2) 0.015(2) 0.0011(17) -0.005(2) 0.000(2) C6A 0.025(3) 0.0195(19) 0.017(2) 0.0032(16) 0.0037(19) 0.0064(18) C14A 0.028(3) 0.021(2) 0.0130(19) 0.0035(15) 0.0062(18) 0.0022(18) C1TA 0.023(3) 0.032(2) 0.024(2) 0.0000(18) 0.005(2) 0.006(2) C2TA 0.025(3) 0.045(3) 0.035(3) -0.013(2) 0.004(2) 0.000(2) ClB 0.0241(7) 0.0387(6) 0.0277(6) -0.0020(5) 0.0039(5) 0.0027(5) O1B 0.049(2) 0.0275(17) 0.0268(16) -0.0044(13) 0.0072(15) -0.0136(15) O2B 0.030(2) 0.063(2) 0.0397(19) -0.0091(17) 0.0010(16) 0.0109(19) O14B 0.0323(19) 0.0258(15) 0.0173(14) 0.0047(12) 0.0055(13) 0.0020(13) N1B 0.032(3) 0.039(2) 0.0217(19) -0.0076(16) 0.0020(18) 0.0026(18) N2B 0.038(3) 0.058(3) 0.029(2) -0.0109(19) 0.016(2) 0.005(2) N3B 0.028(2) 0.0267(18) 0.0124(16) -0.0029(13) 0.0040(15) 0.0021(16) N4B 0.037(3) 0.0218(19) 0.0176(18) -0.0026(14) 0.0116(17) 0.0013(18) N5B 0.028(2) 0.028(2) 0.0227(18) 0.0030(16) 0.0068(17) -0.0055(18) C1B 0.027(3) 0.0165(19) 0.0159(19) 0.0025(15) 0.0047(18) 0.0042(18) C2B 0.029(3) 0.016(2) 0.023(2) 0.0030(16) 0.007(2) 0.0047(18) C3B 0.034(3) 0.023(2) 0.015(2) -0.0005(16) -0.003(2) 0.0001(19) C4B 0.048(3) 0.021(2) 0.020(2) 0.0010(17) 0.016(2) 0.005(2) C5B 0.029(3) 0.021(2) 0.027(2) -0.0036(17) 0.012(2) -0.0015(18) C6B 0.023(3) 0.0166(19) 0.018(2) 0.0037(16) 0.0054(18) 0.0025(18) C14B 0.032(3) 0.0166(19) 0.0126(18) 0.0010(15) 0.0081(18) 0.0029(18) C1TB 0.029(3) 0.033(2) 0.021(2) -0.0069(18) -0.002(2) 0.000(2) C2TB 0.021(3) 0.053(3) 0.028(2) -0.010(2) 0.003(2) 0.001(2) _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 ClA C2A 1.730(5) . ? O1A N5A 1.246(4) . ? O2A N5A 1.196(5) . ? O14A C14A 1.404(5) . ? O14A H41A 0.8400 . ? N1A C1TA 1.294(5) . ? N1A N2A 1.390(5) . ? N2A C2TA 1.302(5) . ? N3A C1TA 1.348(5) . ? N3A C2TA 1.351(6) . ? N3A N4A 1.412(4) . ? N4A C14A 1.479(5) . ? N4A H40A 0.92(4) . ? N5A C6A 1.485(5) . ? C1A C2A 1.390(5) . ? C1A C6A 1.392(6) . ? C1A C14A 1.525(5) . ? C2A C3A 1.388(6) . ? C3A C4A 1.388(6) . ? C3A H3A 0.9500 . ? C4A C5A 1.365(6) . ? C4A H4A 0.9500 . ? C5A C6A 1.391(5) . ? C5A H5A 0.9500 . ? C14A H14A 1.0000 . ? C1TA H1TA 0.9500 . ? C2TA H2TA 0.9500 . ? ClB C2B 1.747(4) . ? O1B N5B 1.233(4) . ? O2B N5B 1.211(4) . ? O14B C14B 1.405(5) . ? O14B H41B 0.8400 . ? N1B C1TB 1.305(5) . ? N1B N2B 1.384(5) . ? N2B C2TB 1.313(5) . ? N3B C1TB 1.352(5) . ? N3B C2TB 1.357(5) . ? N3B N4B 1.417(4) . ? N4B C14B 1.472(5) . ? N4B H40B 0.84(4) . ? N5B C6B 1.477(5) . ? C1B C6B 1.395(5) . ? C1B C2B 1.396(6) . ? C1B C14B 1.529(5) . ? C2B C3B 1.383(5) . ? C3B C4B 1.383(6) . ? C3B H3B 0.9500 . ? C4B C5B 1.377(6) . ? C4B H4B 0.9500 . ? C5B C6B 1.386(5) . ? C5B H5B 0.9500 . ? C14B H14B 1.0000 . ? C1TB H1TB 0.9500 . ? C2TB H2TB 0.9500 . ? 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 C14A O14A H41A 109.5 . . ? C1TA N1A N2A 107.5(3) . . ? C2TA N2A N1A 106.2(4) . . ? C1TA N3A C2TA 105.1(3) . . ? C1TA N3A N4A 128.1(4) . . ? C2TA N3A N4A 126.8(3) . . ? N3A N4A C14A 111.2(3) . . ? N3A N4A H40A 105(2) . . ? C14A N4A H40A 114(3) . . ? O2A N5A O1A 125.3(4) . . ? O2A N5A C6A 118.7(3) . . ? O1A N5A C6A 115.7(4) . . ? C2A C1A C6A 115.2(3) . . ? C2A C1A C14A 121.4(4) . . ? C6A C1A C14A 123.2(3) . . ? C3A C2A C1A 122.8(4) . . ? C3A C2A ClA 118.1(3) . . ? C1A C2A ClA 119.0(3) . . ? C4A C3A C2A 119.2(4) . . ? C4A C3A H3A 120.4 . . ? C2A C3A H3A 120.4 . . ? C5A C4A C3A 120.2(4) . . ? C5A C4A H4A 119.9 . . ? C3A C4A H4A 119.9 . . ? C4A C5A C6A 119.1(4) . . ? C4A C5A H5A 120.5 . . ? C6A C5A H5A 120.5 . . ? C5A C6A C1A 123.3(4) . . ? C5A C6A N5A 116.2(4) . . ? C1A C6A N5A 120.4(3) . . ? O14A C14A N4A 113.3(3) . . ? O14A C14A C1A 111.5(3) . . ? N4A C14A C1A 106.4(3) . . ? O14A C14A H14A 108.5 . . ? N4A C14A H14A 108.5 . . ? C1A C14A H14A 108.5 . . ? N1A C1TA N3A 110.5(4) . . ? N1A C1TA H1TA 124.8 . . ? N3A C1TA H1TA 124.8 . . ? N2A C2TA N3A 110.8(4) . . ? N2A C2TA H2TA 124.6 . . ? N3A C2TA H2TA 124.6 . . ? C14B O14B H41B 109.5 . . ? C1TB N1B N2B 107.8(3) . . ? C2TB N2B N1B 106.8(3) . . ? C1TB N3B C2TB 105.9(3) . . ? C1TB N3B N4B 128.4(4) . . ? C2TB N3B N4B 125.5(4) . . ? N3B N4B C14B 110.8(3) . . ? N3B N4B H40B 100(3) . . ? C14B N4B H40B 108(3) . . ? O2B N5B O1B 124.0(4) . . ? O2B N5B C6B 117.9(4) . . ? O1B N5B C6B 118.0(4) . . ? C6B C1B C2B 114.8(3) . . ? C6B C1B C14B 123.8(4) . . ? C2B C1B C14B 121.4(4) . . ? C3B C2B C1B 122.7(4) . . ? C3B C2B ClB 118.5(3) . . ? C1B C2B ClB 118.8(3) . . ? C2B C3B C4B 119.9(4) . . ? C2B C3B H3B 120.0 . . ? C4B C3B H3B 120.0 . . ? C5B C4B C3B 119.9(4) . . ? C5B C4B H4B 120.1 . . ? C3B C4B H4B 120.1 . . ? C4B C5B C6B 118.6(4) . . ? C4B C5B H5B 120.7 . . ? C6B C5B H5B 120.7 . . ? C5B C6B C1B 124.1(4) . . ? C5B C6B N5B 115.7(4) . . ? C1B C6B N5B 120.2(3) . . ? O14B C14B N4B 114.9(3) . . ? O14B C14B C1B 110.3(3) . . ? N4B C14B C1B 105.9(3) . . ? O14B C14B H14B 108.5 . . ? N4B C14B H14B 108.5 . . ? C1B C14B H14B 108.5 . . ? N1B C1TB N3B 109.7(4) . . ? N1B C1TB H1TB 125.1 . . ? N3B C1TB H1TB 125.1 . . ? N2B C2TB N3B 109.8(4) . . ? N2B C2TB H2TB 125.1 . . ? N3B C2TB H2TB 125.1 . . ? 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 C1TA N1A N2A C2TA -1.4(5) . . . . ? C1TA N3A N4A C14A 89.0(5) . . . . ? C2TA N3A N4A C14A -92.1(5) . . . . ? C6A C1A C2A C3A 2.9(6) . . . . ? C14A C1A C2A C3A -172.9(4) . . . . ? C6A C1A C2A ClA -178.8(3) . . . . ? C14A C1A C2A ClA 5.4(5) . . . . ? C1A C2A C3A C4A -1.0(6) . . . . ? ClA C2A C3A C4A -179.3(3) . . . . ? C2A C3A C4A C5A -0.9(6) . . . . ? C3A C4A C5A C6A 0.7(6) . . . . ? C4A C5A C6A C1A 1.5(6) . . . . ? C4A C5A C6A N5A -175.4(4) . . . . ? C2A C1A C6A C5A -3.1(5) . . . . ? C14A C1A C6A C5A 172.6(4) . . . . ? C2A C1A C6A N5A 173.6(3) . . . . ? C14A C1A C6A N5A -10.7(5) . . . . ? O2A N5A C6A C5A -49.8(5) . . . . ? O1A N5A C6A C5A 124.2(4) . . . . ? O2A N5A C6A C1A 133.2(4) . . . . ? O1A N5A C6A C1A -52.7(5) . . . . ? N3A N4A C14A O14A -54.0(5) . . . . ? N3A N4A C14A C1A -176.8(3) . . . . ? C2A C1A C14A O14A 151.9(3) . . . . ? C6A C1A C14A O14A -23.6(5) . . . . ? C2A C1A C14A N4A -84.2(4) . . . . ? C6A C1A C14A N4A 100.4(4) . . . . ? N2A N1A C1TA N3A 1.3(5) . . . . ? C2TA N3A C1TA N1A -0.6(5) . . . . ? N4A N3A C1TA N1A 178.4(3) . . . . ? N1A N2A C2TA N3A 1.0(5) . . . . ? C1TA N3A C2TA N2A -0.3(5) . . . . ? N4A N3A C2TA N2A -179.4(3) . . . . ? C1TB N1B N2B C2TB -0.2(5) . . . . ? C1TB N3B N4B C14B 73.0(5) . . . . ? C2TB N3B N4B C14B -112.4(4) . . . . ? C6B C1B C2B C3B 2.5(5) . . . . ? C14B C1B C2B C3B -174.5(3) . . . . ? C6B C1B C2B ClB -179.2(3) . . . . ? C14B C1B C2B ClB 3.8(5) . . . . ? C1B C2B C3B C4B -0.8(6) . . . . ? ClB C2B C3B C4B -179.1(3) . . . . ? C2B C3B C4B C5B -0.9(6) . . . . ? C3B C4B C5B C6B 0.6(6) . . . . ? C4B C5B C6B C1B 1.4(6) . . . . ? C4B C5B C6B N5B -177.0(3) . . . . ? C2B C1B C6B C5B -2.8(5) . . . . ? C14B C1B C6B C5B 174.1(4) . . . . ? C2B C1B C6B N5B 175.5(3) . . . . ? C14B C1B C6B N5B -7.6(5) . . . . ? O2B N5B C6B C5B -48.3(5) . . . . ? O1B N5B C6B C5B 127.4(4) . . . . ? O2B N5B C6B C1B 133.2(4) . . . . ? O1B N5B C6B C1B -51.1(5) . . . . ? N3B N4B C14B O14B -55.6(5) . . . . ? N3B N4B C14B C1B -177.6(3) . . . . ? C6B C1B C14B O14B -32.1(5) . . . . ? C2B C1B C14B O14B 144.6(3) . . . . ? C6B C1B C14B N4B 92.8(4) . . . . ? C2B C1B C14B N4B -90.5(4) . . . . ? N2B N1B C1TB N3B 0.4(5) . . . . ? C2TB N3B C1TB N1B -0.4(5) . . . . ? N4B N3B C1TB N1B 175.0(4) . . . . ? N1B N2B C2TB N3B -0.1(5) . . . . ? C1TB N3B C2TB N2B 0.3(5) . . . . ? N4B N3B C2TB N2B -175.3(4) . . . . ? _diffrn_measured_fraction_theta_max 0.953 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.448 _refine_diff_density_min -0.279 _refine_diff_density_rms 0.073 data_6 _database_code_depnum_ccdc_archive 'CCDC 751221' #TrackingRef '- 17.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (4-chloro-3-nitrophenyl)(4H-1,2,4-triazole-4-ylamino)methanol ; _chemical_name_common (4-chloro-3-nitrophenyl)(4H-1,2,4-triazole-4-ylamino)methanol _chemical_melting_point ? _chemical_formula_moiety 'C9 H8 Cl1 N5 O3' _chemical_formula_sum 'C9 H8 Cl N5 O3' _chemical_formula_weight 269.65 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.143(2) _cell_length_b 21.329(6) _cell_length_c 7.429(2) _cell_angle_alpha 90.00 _cell_angle_beta 94.31(3) _cell_angle_gamma 90.00 _cell_volume 1128.6(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2699 _cell_measurement_theta_min 3.35 _cell_measurement_theta_max 28.64 _exptl_crystal_description needles _exptl_crystal_colour yellow _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.587 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.348 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 KM4-CCD _diffrn_measurement_method /w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7678 _diffrn_reflns_av_R_equivalents 0.0195 _diffrn_reflns_av_sigmaI/netI 0.0186 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.35 _diffrn_reflns_theta_max 28.64 _reflns_number_total 2699 _reflns_number_gt 2353 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.0543P)^2^+0.3384P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2699 _refine_ls_number_parameters 195 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0409 _refine_ls_R_factor_gt 0.0350 _refine_ls_wR_factor_ref 0.0954 _refine_ls_wR_factor_gt 0.0928 _refine_ls_goodness_of_fit_ref 1.103 _refine_ls_restrained_S_all 1.103 _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 Cl1 Cl 0.27838(5) 0.463096(19) 0.82785(5) 0.02752(12) Uani 1 1 d . . . O1 O 0.84541(17) 0.41960(6) 0.69360(18) 0.0332(3) Uani 1 1 d . . . O2 O 0.6373(2) 0.40411(6) 0.88247(19) 0.0437(4) Uani 1 1 d . . . O14 O 0.72000(15) 0.69904(5) 0.45722(14) 0.0206(2) Uani 1 1 d . . . H41 H 0.757(3) 0.7023(10) 0.357(3) 0.039(6) Uiso 1 1 d . . . N1 N 0.73645(17) 0.75411(6) 0.99793(16) 0.0198(3) Uani 1 1 d . . . N2 N 0.82351(18) 0.70683(6) 1.10186(16) 0.0206(3) Uani 1 1 d . . . N3 N 0.89118(15) 0.69437(5) 0.82225(15) 0.0139(2) Uani 1 1 d . . . N4 N 0.96695(16) 0.66546(5) 0.67291(15) 0.0155(2) Uani 1 1 d . . . H40 H 1.046(3) 0.6905(9) 0.632(2) 0.022(4) Uiso 1 1 d . . . N5 N 0.70686(18) 0.43619(6) 0.77016(17) 0.0216(3) Uani 1 1 d . . . C1 C 0.68729(19) 0.60136(6) 0.61098(17) 0.0161(3) Uani 1 1 d . . . C2 C 0.74906(19) 0.54147(6) 0.65616(18) 0.0165(3) Uani 1 1 d . . . H2 H 0.876(2) 0.5284(7) 0.644(2) 0.015(4) Uiso 1 1 d . . . C3 C 0.6276(2) 0.49822(6) 0.72515(17) 0.0178(3) Uani 1 1 d . . . C4 C 0.44189(19) 0.51422(7) 0.75047(18) 0.0187(3) Uani 1 1 d . . . C5 C 0.3813(2) 0.57423(7) 0.70552(19) 0.0203(3) Uani 1 1 d . . . H5 H 0.254(3) 0.5853(9) 0.723(3) 0.027(5) Uiso 1 1 d . . . C6 C 0.5023(2) 0.61746(7) 0.63619(19) 0.0193(3) Uani 1 1 d . . . H6 H 0.459(2) 0.6588(8) 0.609(2) 0.020(4) Uiso 1 1 d . . . C14 C 0.82043(19) 0.64749(6) 0.53323(18) 0.0161(3) Uani 1 1 d . . . H14 H 0.890(2) 0.6268(8) 0.445(2) 0.012(4) Uiso 1 1 d . . . C1T C 0.7802(2) 0.74566(7) 0.83182(19) 0.0189(3) Uani 1 1 d . . . H1T H 0.744(2) 0.7700(8) 0.734(3) 0.021(4) Uiso 1 1 d . . . C2T C 0.9140(2) 0.67223(7) 0.99247(19) 0.0187(3) Uani 1 1 d . . . H2T H 0.988(3) 0.6350(9) 1.021(2) 0.027(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0294(2) 0.0341(2) 0.01937(19) -0.00163(14) 0.00408(14) -0.01457(15) O1 0.0263(6) 0.0276(6) 0.0464(7) 0.0074(5) 0.0065(5) 0.0078(5) O2 0.0659(9) 0.0282(6) 0.0399(7) 0.0142(5) 0.0237(7) 0.0084(6) O14 0.0275(5) 0.0223(5) 0.0124(5) 0.0030(4) 0.0034(4) 0.0036(4) N1 0.0221(6) 0.0216(6) 0.0159(6) -0.0022(4) 0.0018(4) 0.0016(5) N2 0.0260(6) 0.0217(6) 0.0145(6) 0.0009(5) 0.0030(5) -0.0016(5) N3 0.0148(5) 0.0149(5) 0.0122(5) 0.0005(4) 0.0024(4) -0.0002(4) N4 0.0159(5) 0.0169(5) 0.0143(5) -0.0010(4) 0.0057(4) -0.0006(4) N5 0.0278(7) 0.0191(6) 0.0176(6) 0.0007(5) -0.0016(5) 0.0001(5) C1 0.0188(6) 0.0183(6) 0.0112(6) -0.0024(5) 0.0010(5) -0.0014(5) C2 0.0172(6) 0.0190(7) 0.0130(6) -0.0021(5) -0.0005(5) 0.0008(5) C3 0.0229(7) 0.0183(6) 0.0120(6) -0.0016(5) -0.0010(5) 0.0013(5) C4 0.0201(7) 0.0238(7) 0.0123(6) -0.0022(5) 0.0011(5) -0.0063(6) C5 0.0175(7) 0.0263(7) 0.0174(7) -0.0026(5) 0.0027(5) 0.0016(6) C6 0.0213(7) 0.0197(7) 0.0169(7) -0.0005(5) 0.0023(5) 0.0038(5) C14 0.0193(6) 0.0178(6) 0.0116(6) -0.0005(5) 0.0037(5) 0.0013(5) C1T 0.0219(7) 0.0187(7) 0.0159(7) -0.0004(5) 0.0011(5) 0.0048(5) C2T 0.0215(7) 0.0196(7) 0.0148(6) 0.0034(5) 0.0004(5) 0.0002(5) _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 Cl1 C4 1.7276(15) . ? O1 N5 1.2299(18) . ? O2 N5 1.2140(17) . ? O14 C14 1.4077(17) . ? O14 H41 0.81(2) . ? N1 C1T 1.3079(19) . ? N1 N2 1.3884(18) . ? N2 C2T 1.3044(19) . ? N3 C2T 1.3482(18) . ? N3 C1T 1.3562(18) . ? N3 N4 1.4122(16) . ? N4 C14 1.4682(18) . ? N4 H40 0.849(19) . ? N5 C3 1.4679(19) . ? C1 C2 1.3845(19) . ? C1 C6 1.392(2) . ? C1 C14 1.5129(19) . ? C2 C3 1.390(2) . ? C2 H2 0.960(18) . ? C3 C4 1.396(2) . ? C4 C5 1.384(2) . ? C5 C6 1.389(2) . ? C5 H5 0.956(18) . ? C6 H6 0.950(18) . ? C14 H14 0.960(16) . ? C1T H1T 0.914(19) . ? C2T H2T 0.970(19) . ? 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 C14 O14 H41 104.2(16) . . ? C1T N1 N2 107.22(12) . . ? C2T N2 N1 106.66(12) . . ? C2T N3 C1T 105.27(12) . . ? C2T N3 N4 123.88(11) . . ? C1T N3 N4 130.81(11) . . ? N3 N4 C14 111.98(11) . . ? N3 N4 H40 108.2(12) . . ? C14 N4 H40 111.5(12) . . ? O2 N5 O1 122.76(13) . . ? O2 N5 C3 119.57(13) . . ? O1 N5 C3 117.65(12) . . ? C2 C1 C6 118.92(13) . . ? C2 C1 C14 119.64(12) . . ? C6 C1 C14 121.43(13) . . ? C1 C2 C3 120.34(13) . . ? C1 C2 H2 122.1(10) . . ? C3 C2 H2 117.5(10) . . ? C2 C3 C4 120.88(13) . . ? C2 C3 N5 116.18(12) . . ? C4 C3 N5 122.95(13) . . ? C5 C4 C3 118.46(13) . . ? C5 C4 Cl1 117.20(11) . . ? C3 C4 Cl1 124.30(12) . . ? C4 C5 C6 120.77(13) . . ? C4 C5 H5 118.6(12) . . ? C6 C5 H5 120.6(12) . . ? C5 C6 C1 120.64(13) . . ? C5 C6 H6 119.8(11) . . ? C1 C6 H6 119.6(11) . . ? O14 C14 N4 113.22(11) . . ? O14 C14 C1 110.19(11) . . ? N4 C14 C1 109.58(11) . . ? O14 C14 H14 111.2(9) . . ? N4 C14 H14 102.9(10) . . ? C1 C14 H14 109.5(10) . . ? N1 C1T N3 110.03(13) . . ? N1 C1T H1T 127.0(11) . . ? N3 C1T H1T 123.0(11) . . ? N2 C2T N3 110.83(13) . . ? N2 C2T H2T 128.2(11) . . ? N3 C2T H2T 121.0(11) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1T N1 N2 C2T -0.40(16) . . . . ? C2T N3 N4 C14 120.63(14) . . . . ? C1T N3 N4 C14 -56.67(18) . . . . ? C6 C1 C2 C3 0.2(2) . . . . ? C14 C1 C2 C3 -179.01(12) . . . . ? C1 C2 C3 C4 -0.1(2) . . . . ? C1 C2 C3 N5 -179.54(12) . . . . ? O2 N5 C3 C2 155.22(14) . . . . ? O1 N5 C3 C2 -23.24(18) . . . . ? O2 N5 C3 C4 -24.2(2) . . . . ? O1 N5 C3 C4 157.34(14) . . . . ? C2 C3 C4 C5 -0.1(2) . . . . ? N5 C3 C4 C5 179.31(12) . . . . ? C2 C3 C4 Cl1 177.68(10) . . . . ? N5 C3 C4 Cl1 -2.93(19) . . . . ? C3 C4 C5 C6 0.2(2) . . . . ? Cl1 C4 C5 C6 -177.68(11) . . . . ? C4 C5 C6 C1 -0.2(2) . . . . ? C2 C1 C6 C5 0.0(2) . . . . ? C14 C1 C6 C5 179.14(12) . . . . ? N3 N4 C14 O14 62.96(14) . . . . ? N3 N4 C14 C1 -60.49(14) . . . . ? C2 C1 C14 O14 165.79(12) . . . . ? C6 C1 C14 O14 -13.36(17) . . . . ? C2 C1 C14 N4 -68.99(15) . . . . ? C6 C1 C14 N4 111.86(14) . . . . ? N2 N1 C1T N3 0.53(16) . . . . ? C2T N3 C1T N1 -0.45(16) . . . . ? N4 N3 C1T N1 177.22(13) . . . . ? N1 N2 C2T N3 0.12(16) . . . . ? C1T N3 C2T N2 0.19(16) . . . . ? N4 N3 C2T N2 -177.69(12) . . . . ? _diffrn_measured_fraction_theta_max 0.931 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.419 _refine_diff_density_min -0.259 _refine_diff_density_rms 0.058 data_7 _database_code_depnum_ccdc_archive 'CCDC 751222' #TrackingRef '- 17.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (4-chloro-3-nitrophenyl)(4H-1,2,4-triazole-4-ylamino)methanol ; _chemical_name_common (4-chloro-3-nitrophenyl)(4H-1,2,4-triazole-4-ylamino)methanol _chemical_melting_point ? _chemical_formula_moiety 'C9 H8 Cl1 N5 O3' _chemical_formula_sum 'C9 H8 Cl N5 O3' _chemical_formula_weight 269.65 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.386(4) _cell_length_b 10.764(3) _cell_length_c 8.407(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.08(2) _cell_angle_gamma 90.00 _cell_volume 1119.2(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1985 _cell_measurement_theta_min 3.08 _cell_measurement_theta_max 25.06 _exptl_crystal_description plates _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.600 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.351 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 KM4-CCD _diffrn_measurement_method /w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11195 _diffrn_reflns_av_R_equivalents 0.0259 _diffrn_reflns_av_sigmaI/netI 0.0142 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 25.06 _reflns_number_total 1985 _reflns_number_gt 1720 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.0407P)^2^+0.5287P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1985 _refine_ls_number_parameters 195 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0355 _refine_ls_R_factor_gt 0.0286 _refine_ls_wR_factor_ref 0.0755 _refine_ls_wR_factor_gt 0.0717 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.39299(3) -0.03923(4) 0.80718(5) 0.02837(15) Uani 1 1 d . . . O1 O 0.52283(10) 0.28414(13) 0.99083(14) 0.0302(3) Uani 1 1 d . . . O2 O 0.57377(10) 0.14371(13) 0.82591(15) 0.0315(3) Uani 1 1 d . . . O14 O 0.13532(9) 0.45898(11) 0.50258(13) 0.0171(3) Uani 1 1 d . . . H41 H 0.1395(17) 0.528(2) 0.448(3) 0.036(6) Uiso 1 1 d . . . N1 N 0.04211(11) 0.80639(13) 0.72829(16) 0.0204(3) Uani 1 1 d . . . N2 N 0.13372(11) 0.82745(13) 0.82838(17) 0.0233(3) Uani 1 1 d . . . N3 N 0.12448(10) 0.62913(12) 0.77717(15) 0.0163(3) Uani 1 1 d . . . N4 N 0.15419(11) 0.50208(12) 0.78262(16) 0.0169(3) Uani 1 1 d . . . H40 H 0.0960(16) 0.4583(19) 0.791(2) 0.025(5) Uiso 1 1 d . . . N5 N 0.50531(11) 0.21304(14) 0.87844(16) 0.0231(3) Uani 1 1 d . . . C1 C 0.25559(12) 0.33767(15) 0.67209(17) 0.0149(3) Uani 1 1 d . . . C2 C 0.35227(12) 0.32993(16) 0.76417(18) 0.0167(3) Uani 1 1 d . . . H2 H 0.3885(14) 0.4023(18) 0.800(2) 0.019(4) Uiso 1 1 d . . . C3 C 0.39758(12) 0.21472(16) 0.79737(18) 0.0182(3) Uani 1 1 d . . . C4 C 0.34555(13) 0.10581(15) 0.74862(18) 0.0196(4) Uani 1 1 d . . . C5 C 0.24890(13) 0.11362(16) 0.65855(19) 0.0200(4) Uani 1 1 d . . . H5 H 0.2096(15) 0.0381(18) 0.623(2) 0.024(5) Uiso 1 1 d . . . C6 C 0.20590(13) 0.22894(15) 0.61750(19) 0.0173(3) Uani 1 1 d . . . H6 H 0.1427(15) 0.2345(17) 0.552(2) 0.021(5) Uiso 1 1 d . . . C14 C 0.20699(12) 0.46446(15) 0.63711(18) 0.0148(3) Uani 1 1 d . . . H14 H 0.2632(14) 0.5244(16) 0.6226(19) 0.013(4) Uiso 1 1 d . . . C1T C 0.03981(13) 0.68704(15) 0.69873(19) 0.0188(3) Uani 1 1 d . . . H1T H -0.0122(15) 0.6448(18) 0.632(2) 0.026(5) Uiso 1 1 d . . . C2T C 0.18046(14) 0.72026(16) 0.8555(2) 0.0229(4) Uani 1 1 d . . . H2T H 0.2447(16) 0.7048(18) 0.921(2) 0.029(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0303(3) 0.0204(2) 0.0348(3) 0.00934(18) 0.00525(18) 0.01191(17) O1 0.0243(7) 0.0429(8) 0.0230(7) 0.0017(6) -0.0043(5) 0.0025(6) O2 0.0205(6) 0.0403(8) 0.0339(7) 0.0077(6) 0.0037(5) 0.0154(6) O14 0.0201(6) 0.0127(6) 0.0177(6) 0.0029(5) -0.0056(4) -0.0010(4) N1 0.0178(7) 0.0169(7) 0.0262(7) -0.0037(6) -0.0011(6) 0.0012(5) N2 0.0218(7) 0.0186(8) 0.0291(8) -0.0067(6) -0.0037(6) 0.0002(6) N3 0.0178(7) 0.0117(7) 0.0190(7) -0.0029(5) -0.0015(5) 0.0012(5) N4 0.0189(7) 0.0100(7) 0.0218(7) -0.0001(5) 0.0003(5) 0.0029(5) N5 0.0184(7) 0.0313(9) 0.0196(7) 0.0090(6) 0.0017(6) 0.0056(6) C1 0.0140(7) 0.0166(8) 0.0145(7) 0.0013(6) 0.0045(6) 0.0023(6) C2 0.0153(8) 0.0182(9) 0.0170(8) 0.0006(6) 0.0029(6) 0.0014(6) C3 0.0153(8) 0.0246(9) 0.0150(8) 0.0037(6) 0.0032(6) 0.0064(6) C4 0.0240(8) 0.0166(9) 0.0190(8) 0.0047(6) 0.0072(6) 0.0086(7) C5 0.0235(8) 0.0166(9) 0.0200(8) -0.0001(7) 0.0026(7) 0.0012(7) C6 0.0177(8) 0.0165(8) 0.0177(8) 0.0005(6) -0.0001(6) 0.0018(6) C14 0.0131(7) 0.0137(8) 0.0175(8) -0.0003(6) -0.0010(6) -0.0009(6) C1T 0.0161(8) 0.0160(8) 0.0239(8) -0.0039(7) -0.0022(7) 0.0012(6) C2T 0.0241(9) 0.0184(9) 0.0253(9) -0.0068(7) -0.0056(7) 0.0018(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 Cl1 C4 1.7303(17) . ? O1 N5 1.2262(19) . ? O2 N5 1.2294(19) . ? O14 C14 1.4010(19) . ? O14 H41 0.88(2) . ? N1 C1T 1.309(2) . ? N1 N2 1.3944(19) . ? N2 C2T 1.305(2) . ? N3 C2T 1.352(2) . ? N3 C1T 1.360(2) . ? N3 N4 1.4163(19) . ? N4 C14 1.474(2) . ? N4 H40 0.87(2) . ? N5 C3 1.465(2) . ? C1 C6 1.389(2) . ? C1 C2 1.393(2) . ? C1 C14 1.514(2) . ? C2 C3 1.383(2) . ? C2 H2 0.941(19) . ? C3 C4 1.389(2) . ? C4 C5 1.384(2) . ? C5 C6 1.387(2) . ? C5 H5 0.985(19) . ? C6 H6 0.934(19) . ? C14 H14 0.962(18) . ? C1T H1T 0.947(19) . ? C2T H2T 0.96(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C14 O14 H41 109.5(14) . . ? C1T N1 N2 106.43(13) . . ? C2T N2 N1 107.49(13) . . ? C2T N3 C1T 105.41(14) . . ? C2T N3 N4 124.01(13) . . ? C1T N3 N4 130.58(13) . . ? N3 N4 C14 111.37(12) . . ? N3 N4 H40 108.2(13) . . ? C14 N4 H40 109.0(13) . . ? O1 N5 O2 123.97(14) . . ? O1 N5 C3 118.02(13) . . ? O2 N5 C3 117.96(14) . . ? C6 C1 C2 119.06(14) . . ? C6 C1 C14 122.07(13) . . ? C2 C1 C14 118.86(14) . . ? C3 C2 C1 119.54(15) . . ? C3 C2 H2 119.7(11) . . ? C1 C2 H2 120.7(11) . . ? C2 C3 C4 121.35(15) . . ? C2 C3 N5 117.02(15) . . ? C4 C3 N5 121.55(14) . . ? C5 C4 C3 118.95(15) . . ? C5 C4 Cl1 118.75(13) . . ? C3 C4 Cl1 122.17(13) . . ? C4 C5 C6 119.98(15) . . ? C4 C5 H5 120.9(11) . . ? C6 C5 H5 119.1(11) . . ? C5 C6 C1 120.97(15) . . ? C5 C6 H6 120.2(11) . . ? C1 C6 H6 118.9(11) . . ? O14 C14 N4 113.04(12) . . ? O14 C14 C1 110.30(12) . . ? N4 C14 C1 106.01(12) . . ? O14 C14 H14 110.9(10) . . ? N4 C14 H14 106.1(10) . . ? C1 C14 H14 110.3(10) . . ? N1 C1T N3 110.46(14) . . ? N1 C1T H1T 126.2(12) . . ? N3 C1T H1T 123.3(12) . . ? N2 C2T N3 110.20(15) . . ? N2 C2T H2T 126.9(12) . . ? N3 C2T H2T 122.9(12) . . ? 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 C1T N1 N2 C2T -0.92(18) . . . . ? C2T N3 N4 C14 -102.03(17) . . . . ? C1T N3 N4 C14 77.9(2) . . . . ? C6 C1 C2 C3 0.9(2) . . . . ? C14 C1 C2 C3 179.89(13) . . . . ? C1 C2 C3 C4 -3.8(2) . . . . ? C1 C2 C3 N5 172.98(13) . . . . ? O1 N5 C3 C2 44.15(19) . . . . ? O2 N5 C3 C2 -133.22(16) . . . . ? O1 N5 C3 C4 -139.08(16) . . . . ? O2 N5 C3 C4 43.5(2) . . . . ? C2 C3 C4 C5 3.1(2) . . . . ? N5 C3 C4 C5 -173.53(14) . . . . ? C2 C3 C4 Cl1 -172.73(12) . . . . ? N5 C3 C4 Cl1 10.7(2) . . . . ? C3 C4 C5 C6 0.4(2) . . . . ? Cl1 C4 C5 C6 176.39(12) . . . . ? C4 C5 C6 C1 -3.3(2) . . . . ? C2 C1 C6 C5 2.5(2) . . . . ? C14 C1 C6 C5 -176.37(14) . . . . ? N3 N4 C14 O14 -70.90(16) . . . . ? N3 N4 C14 C1 168.15(12) . . . . ? C6 C1 C14 O14 -22.03(19) . . . . ? C2 C1 C14 O14 159.05(13) . . . . ? C6 C1 C14 N4 100.67(16) . . . . ? C2 C1 C14 N4 -78.25(16) . . . . ? N2 N1 C1T N3 1.11(18) . . . . ? C2T N3 C1T N1 -0.87(18) . . . . ? N4 N3 C1T N1 179.22(14) . . . . ? N1 N2 C2T N3 0.40(19) . . . . ? C1T N3 C2T N2 0.26(19) . . . . ? N4 N3 C2T N2 -179.82(14) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.06 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.266 _refine_diff_density_min -0.154 _refine_diff_density_rms 0.052 data_4a _database_code_depnum_ccdc_archive 'CCDC 751223' #TrackingRef '- 17.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N-(2,4-dinitrobenzylidene)-4H-1,2,4-triazole-4-amine ; _chemical_name_common N-(2,4-dinitrobenzylidene)-4H-1,2,4-triazole-4-amine _chemical_melting_point ? _chemical_formula_moiety 'C9 H6 N6 O4' _chemical_formula_sum 'C9 H6 N6 O4' _chemical_formula_weight 262.20 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 P21/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 16.286(5) _cell_length_b 7.007(2) _cell_length_c 19.746(6) _cell_angle_alpha 90.00 _cell_angle_beta 91.24(3) _cell_angle_gamma 90.00 _cell_volume 2252.8(12) _cell_formula_units_Z 8 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 5577 _cell_measurement_theta_min 3.09 _cell_measurement_theta_max 28.75 _exptl_crystal_description needles _exptl_crystal_colour colorless _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.546 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1072 _exptl_absorpt_coefficient_mu 0.126 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 KM4-CCD _diffrn_measurement_method /w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 31807 _diffrn_reflns_av_R_equivalents 0.0578 _diffrn_reflns_av_sigmaI/netI 0.0694 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 28.75 _reflns_number_total 5577 _reflns_number_gt 2376 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.0566P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5577 _refine_ls_number_parameters 343 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1489 _refine_ls_R_factor_gt 0.0487 _refine_ls_wR_factor_ref 0.1307 _refine_ls_wR_factor_gt 0.0973 _refine_ls_goodness_of_fit_ref 0.952 _refine_ls_restrained_S_all 0.952 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1A O -0.19350(13) 0.9410(3) 0.21528(11) 0.0965(7) Uani 1 1 d . . . O2A O -0.29340(12) 0.8059(3) 0.26765(10) 0.1031(7) Uani 1 1 d . . . O3A O -0.23670(13) 0.7934(4) 0.51130(10) 0.1164(8) Uani 1 1 d . . . O4A O -0.13008(15) 0.6273(4) 0.54299(11) 0.1101(8) Uani 1 1 d . . . N1A N 0.15830(12) 0.7559(3) 0.09027(11) 0.0662(5) Uani 1 1 d . . . N2A N 0.08731(13) 0.6879(3) 0.05766(10) 0.0696(6) Uani 1 1 d . . . N3A N 0.06157(10) 0.7284(2) 0.16435(9) 0.0492(4) Uani 1 1 d . . . N4A N 0.02861(11) 0.7405(3) 0.22820(9) 0.0531(5) Uani 1 1 d . . . N5A N -0.22121(14) 0.8468(3) 0.26156(12) 0.0731(6) Uani 1 1 d . . . N6A N -0.17137(17) 0.7144(4) 0.50044(13) 0.0836(7) Uani 1 1 d . . . C1A C -0.08224(13) 0.7374(3) 0.30077(11) 0.0483(5) Uani 1 1 d . . . C2A C -0.16327(13) 0.7824(3) 0.31519(12) 0.0557(6) Uani 1 1 d . . . C3A C -0.19314(14) 0.7763(3) 0.37985(13) 0.0628(7) Uani 1 1 d . . . H3A H -0.2475 0.8067 0.3884 0.075 Uiso 1 1 calc R . . C4A C -0.13987(15) 0.7237(3) 0.43128(12) 0.0591(6) Uani 1 1 d . . . C5A C -0.05926(14) 0.6798(3) 0.42058(12) 0.0591(6) Uani 1 1 d . . . H5A H -0.0243 0.6468 0.4566 0.071 Uiso 1 1 calc R . . C6A C -0.03115(13) 0.6857(3) 0.35536(12) 0.0545(6) Uani 1 1 d . . . H6A H 0.0233 0.6544 0.3475 0.065 Uiso 1 1 calc R . . C14A C -0.04831(13) 0.7336(3) 0.23248(11) 0.0515(6) Uani 1 1 d . . . H14A H -0.0822 0.7263 0.1941 0.062 Uiso 1 1 calc R . . C1TA C 0.14089(13) 0.7761(3) 0.15359(13) 0.0556(6) Uani 1 1 d . . . H1TA H 0.1778 0.8177 0.1871 0.067 Uiso 1 1 calc R . . C2TA C 0.03138(15) 0.6737(3) 0.10324(11) 0.0573(6) Uani 1 1 d . . . H2TA H -0.0221 0.6317 0.0949 0.069 Uiso 1 1 calc R . . O1B O 0.35525(10) 0.8972(3) 0.59551(9) 0.0757(5) Uani 1 1 d . . . O2B O 0.33939(12) 0.7377(3) 0.68711(9) 0.1038(7) Uani 1 1 d . . . O3B O 0.52073(14) 0.1799(4) 0.70077(13) 0.1209(9) Uani 1 1 d . . . O4B O 0.53569(12) 0.0089(3) 0.61203(13) 0.1089(8) Uani 1 1 d . . . N1B N 0.20192(12) 0.9623(3) 0.31049(10) 0.0699(6) Uani 1 1 d . . . N2B N 0.14667(11) 0.9405(3) 0.36217(10) 0.0622(5) Uani 1 1 d . . . N3B N 0.26076(10) 0.7984(2) 0.39178(8) 0.0505(5) Uani 1 1 d . . . N4B N 0.32214(10) 0.6915(3) 0.42468(9) 0.0548(5) Uani 1 1 d . . . N5B N 0.35882(11) 0.7500(3) 0.62811(11) 0.0622(5) Uani 1 1 d . . . N6B N 0.50944(13) 0.1487(4) 0.64162(16) 0.0854(7) Uani 1 1 d . . . C1B C 0.36999(11) 0.5484(3) 0.52622(11) 0.0475(5) Uani 1 1 d . . . C2B C 0.38745(12) 0.5766(3) 0.59471(11) 0.0495(5) Uani 1 1 d . . . C3B C 0.43288(12) 0.4481(4) 0.63321(12) 0.0604(6) Uani 1 1 d . . . H3TB H 0.4431 0.4682 0.6792 0.072 Uiso 1 1 calc R . . C4B C 0.46213(13) 0.2908(4) 0.60105(14) 0.0628(7) Uani 1 1 d . . . C5B C 0.44862(14) 0.2583(3) 0.53314(14) 0.0675(7) Uani 1 1 d . . . H5B H 0.4705 0.1509 0.5125 0.081 Uiso 1 1 calc R . . C6B C 0.40232(13) 0.3866(3) 0.49607(12) 0.0573(6) Uani 1 1 d . . . H6B H 0.3925 0.3648 0.4501 0.069 Uiso 1 1 calc R . . C14B C 0.31370(12) 0.6731(3) 0.48793(11) 0.0475(5) Uani 1 1 d . . . H14B H 0.2722 0.7382 0.5099 0.057 Uiso 1 1 calc R . . C1TB C 0.26849(15) 0.8758(4) 0.33005(12) 0.0702(7) Uani 1 1 d . . . H1TB H 0.3157 0.8683 0.3046 0.084 Uiso 1 1 calc R . . C2TB C 0.18308(13) 0.8425(3) 0.40956(11) 0.0548(6) Uani 1 1 d . . . H2TB H 0.1593 0.8074 0.4501 0.066 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 O1A 0.1005(15) 0.0915(15) 0.0969(16) 0.0165(12) -0.0126(12) 0.0149(12) O2A 0.0526(11) 0.1400(19) 0.1163(16) -0.0288(14) -0.0054(11) 0.0133(12) O3A 0.0775(14) 0.176(2) 0.0971(16) -0.0441(15) 0.0332(12) -0.0363(15) O4A 0.131(2) 0.131(2) 0.0688(14) -0.0004(14) 0.0149(13) -0.0361(16) N1A 0.0618(13) 0.0625(13) 0.0749(15) 0.0097(11) 0.0147(11) 0.0065(10) N2A 0.0761(15) 0.0715(15) 0.0617(13) -0.0002(11) 0.0113(12) 0.0013(12) N3A 0.0488(11) 0.0463(11) 0.0525(12) 0.0038(9) 0.0044(9) 0.0005(9) N4A 0.0507(11) 0.0582(12) 0.0506(12) 0.0016(9) 0.0027(9) 0.0001(9) N5A 0.0666(16) 0.0688(15) 0.0835(17) -0.0179(13) -0.0063(13) 0.0137(13) N6A 0.0813(19) 0.097(2) 0.0732(18) -0.0280(15) 0.0172(15) -0.0391(15) C1A 0.0510(13) 0.0359(12) 0.0580(14) -0.0066(11) 0.0021(11) -0.0069(10) C2A 0.0510(13) 0.0457(14) 0.0703(16) -0.0118(12) -0.0013(12) -0.0028(11) C3A 0.0561(15) 0.0536(15) 0.0791(18) -0.0214(13) 0.0125(14) -0.0090(12) C4A 0.0663(16) 0.0544(15) 0.0573(16) -0.0154(12) 0.0161(13) -0.0219(12) C5A 0.0638(16) 0.0538(15) 0.0595(16) -0.0036(12) -0.0007(12) -0.0156(12) C6A 0.0508(13) 0.0486(14) 0.0642(15) -0.0048(12) 0.0015(11) -0.0079(11) C14A 0.0529(14) 0.0448(13) 0.0566(15) -0.0028(11) -0.0047(11) -0.0028(11) C1TA 0.0476(14) 0.0503(14) 0.0690(17) 0.0066(12) 0.0045(12) 0.0055(11) C2TA 0.0605(15) 0.0563(15) 0.0550(15) -0.0001(12) 0.0019(12) -0.0020(12) O1B 0.0808(12) 0.0640(11) 0.0821(13) 0.0003(10) -0.0038(10) 0.0003(10) O2B 0.1174(16) 0.1421(19) 0.0520(12) -0.0004(12) 0.0066(11) 0.0310(14) O3B 0.1163(18) 0.150(2) 0.0953(16) 0.0466(16) -0.0321(14) 0.0300(15) O4B 0.0857(15) 0.0786(14) 0.161(2) 0.0254(15) -0.0355(14) 0.0175(12) N1B 0.0573(12) 0.0931(16) 0.0587(13) 0.0216(12) -0.0091(10) -0.0005(12) N2B 0.0523(11) 0.0719(14) 0.0619(13) 0.0127(11) -0.0087(10) 0.0058(10) N3B 0.0472(11) 0.0600(12) 0.0442(11) 0.0063(9) -0.0042(8) 0.0027(9) N4B 0.0465(10) 0.0677(13) 0.0498(12) 0.0074(10) -0.0063(8) 0.0093(9) N5B 0.0527(12) 0.0816(16) 0.0520(13) 0.0008(12) -0.0062(10) 0.0002(11) N6B 0.0550(14) 0.0813(18) 0.119(2) 0.0346(19) -0.0197(14) 0.0058(13) C1B 0.0341(11) 0.0561(14) 0.0523(14) 0.0113(11) -0.0003(10) -0.0021(10) C2B 0.0373(11) 0.0590(15) 0.0518(14) 0.0071(12) -0.0039(10) -0.0017(11) C3B 0.0422(12) 0.0810(18) 0.0576(15) 0.0156(14) -0.0067(11) -0.0055(13) C4B 0.0450(13) 0.0601(16) 0.0828(19) 0.0243(15) -0.0095(12) 0.0020(12) C5B 0.0548(15) 0.0554(16) 0.092(2) 0.0040(15) -0.0029(14) 0.0077(12) C6B 0.0515(13) 0.0587(15) 0.0616(15) 0.0021(13) -0.0019(11) 0.0039(12) C14B 0.0396(11) 0.0547(14) 0.0481(14) 0.0011(11) -0.0009(10) 0.0027(10) C1TB 0.0550(15) 0.108(2) 0.0479(15) 0.0161(15) -0.0014(11) 0.0021(15) C2TB 0.0443(13) 0.0675(15) 0.0524(14) 0.0081(12) -0.0045(10) 0.0056(12) _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 O1A N5A 1.222(3) . ? O2A N5A 1.219(3) . ? O3A N6A 1.222(3) . ? O4A N6A 1.227(3) . ? N1A C1TA 1.296(3) . ? N1A N2A 1.395(3) . ? N2A C2TA 1.298(3) . ? N3A C2TA 1.349(3) . ? N3A C1TA 1.356(2) . ? N3A N4A 1.383(2) . ? N4A C14A 1.258(2) . ? N5A C2A 1.474(3) . ? N6A C4A 1.471(3) . ? C1A C2A 1.392(3) . ? C1A C6A 1.395(3) . ? C1A C14A 1.469(3) . ? C2A C3A 1.377(3) . ? C3A C4A 1.372(3) . ? C3A H3A 0.9300 . ? C4A C5A 1.369(3) . ? C5A C6A 1.377(3) . ? C5A H5A 0.9300 . ? C6A H6A 0.9300 . ? C14A H14A 0.9300 . ? C1TA H1TA 0.9300 . ? C2TA H2TA 0.9300 . ? O1B N5B 1.217(2) . ? O2B N5B 1.217(2) . ? O3B N6B 1.199(3) . ? O4B N6B 1.223(3) . ? N1B C1TB 1.294(3) . ? N1B N2B 1.383(2) . ? N2B C2TB 1.294(2) . ? N3B C1TB 1.343(3) . ? N3B C2TB 1.356(3) . ? N3B N4B 1.398(2) . ? N4B C14B 1.266(2) . ? N5B C2B 1.464(3) . ? N6B C4B 1.483(3) . ? C1B C6B 1.390(3) . ? C1B C2B 1.390(3) . ? C1B C14B 1.465(3) . ? C2B C3B 1.382(3) . ? C3B C4B 1.363(3) . ? C3B H3TB 0.9300 . ? C4B C5B 1.373(3) . ? C5B C6B 1.374(3) . ? C5B H5B 0.9300 . ? C6B H6B 0.9300 . ? C14B H14B 0.9300 . ? C1TB H1TB 0.9300 . ? C2TB H2TB 0.9300 . ? 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 C1TA N1A N2A 106.64(18) . . ? C2TA N2A N1A 107.03(19) . . ? C2TA N3A C1TA 105.07(19) . . ? C2TA N3A N4A 133.75(18) . . ? C1TA N3A N4A 121.18(19) . . ? C14A N4A N3A 117.74(18) . . ? O2A N5A O1A 125.0(3) . . ? O2A N5A C2A 117.5(3) . . ? O1A N5A C2A 117.5(2) . . ? O3A N6A O4A 124.8(3) . . ? O3A N6A C4A 117.7(3) . . ? O4A N6A C4A 117.4(3) . . ? C2A C1A C6A 116.9(2) . . ? C2A C1A C14A 124.7(2) . . ? C6A C1A C14A 118.33(19) . . ? C3A C2A C1A 122.5(2) . . ? C3A C2A N5A 116.3(2) . . ? C1A C2A N5A 121.2(2) . . ? C4A C3A C2A 117.7(2) . . ? C4A C3A H3A 121.2 . . ? C2A C3A H3A 121.2 . . ? C5A C4A C3A 122.6(2) . . ? C5A C4A N6A 119.2(3) . . ? C3A C4A N6A 118.1(2) . . ? C4A C5A C6A 118.5(2) . . ? C4A C5A H5A 120.8 . . ? C6A C5A H5A 120.8 . . ? C5A C6A C1A 121.7(2) . . ? C5A C6A H6A 119.1 . . ? C1A C6A H6A 119.1 . . ? N4A C14A C1A 117.1(2) . . ? N4A C14A H14A 121.4 . . ? C1A C14A H14A 121.4 . . ? N1A C1TA N3A 110.7(2) . . ? N1A C1TA H1TA 124.7 . . ? N3A C1TA H1TA 124.7 . . ? N2A C2TA N3A 110.5(2) . . ? N2A C2TA H2TA 124.7 . . ? N3A C2TA H2TA 124.7 . . ? C1TB N1B N2B 106.41(18) . . ? C2TB N2B N1B 107.26(18) . . ? C1TB N3B C2TB 104.42(18) . . ? C1TB N3B N4B 123.94(19) . . ? C2TB N3B N4B 131.59(18) . . ? C14B N4B N3B 114.91(17) . . ? O1B N5B O2B 123.8(2) . . ? O1B N5B C2B 118.5(2) . . ? O2B N5B C2B 117.7(2) . . ? O3B N6B O4B 124.3(3) . . ? O3B N6B C4B 118.1(3) . . ? O4B N6B C4B 117.6(3) . . ? C6B C1B C2B 117.5(2) . . ? C6B C1B C14B 120.3(2) . . ? C2B C1B C14B 122.0(2) . . ? C3B C2B C1B 122.6(2) . . ? C3B C2B N5B 117.7(2) . . ? C1B C2B N5B 119.72(19) . . ? C4B C3B C2B 117.3(2) . . ? C4B C3B H3TB 121.3 . . ? C2B C3B H3TB 121.3 . . ? C3B C4B C5B 122.6(2) . . ? C3B C4B N6B 118.3(3) . . ? C5B C4B N6B 119.1(3) . . ? C4B C5B C6B 119.1(2) . . ? C4B C5B H5B 120.5 . . ? C6B C5B H5B 120.5 . . ? C5B C6B C1B 120.9(2) . . ? C5B C6B H6B 119.5 . . ? C1B C6B H6B 119.5 . . ? N4B C14B C1B 119.32(19) . . ? N4B C14B H14B 120.3 . . ? C1B C14B H14B 120.3 . . ? N1B C1TB N3B 111.5(2) . . ? N1B C1TB H1TB 124.3 . . ? N3B C1TB H1TB 124.3 . . ? N2B C2TB N3B 110.5(2) . . ? N2B C2TB H2TB 124.8 . . ? N3B C2TB H2TB 124.8 . . ? 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 C1TA N1A N2A C2TA 0.8(2) . . . . ? C2TA N3A N4A C14A -15.3(3) . . . . ? C1TA N3A N4A C14A 165.33(19) . . . . ? C6A C1A C2A C3A -0.4(3) . . . . ? C14A C1A C2A C3A 177.17(19) . . . . ? C6A C1A C2A N5A 177.35(19) . . . . ? C14A C1A C2A N5A -5.1(3) . . . . ? O2A N5A C2A C3A -33.4(3) . . . . ? O1A N5A C2A C3A 144.8(2) . . . . ? O2A N5A C2A C1A 148.7(2) . . . . ? O1A N5A C2A C1A -33.0(3) . . . . ? C1A C2A C3A C4A 0.1(3) . . . . ? N5A C2A C3A C4A -177.7(2) . . . . ? C2A C3A C4A C5A 0.6(3) . . . . ? C2A C3A C4A N6A -179.3(2) . . . . ? O3A N6A C4A C5A 164.0(2) . . . . ? O4A N6A C4A C5A -16.1(3) . . . . ? O3A N6A C4A C3A -16.0(3) . . . . ? O4A N6A C4A C3A 163.8(2) . . . . ? C3A C4A C5A C6A -1.2(3) . . . . ? N6A C4A C5A C6A 178.8(2) . . . . ? C4A C5A C6A C1A 0.9(3) . . . . ? C2A C1A C6A C5A -0.2(3) . . . . ? C14A C1A C6A C5A -177.87(19) . . . . ? N3A N4A C14A C1A 177.20(16) . . . . ? C2A C1A C14A N4A 161.7(2) . . . . ? C6A C1A C14A N4A -20.8(3) . . . . ? N2A N1A C1TA N3A -1.2(2) . . . . ? C2TA N3A C1TA N1A 1.1(2) . . . . ? N4A N3A C1TA N1A -179.38(18) . . . . ? N1A N2A C2TA N3A -0.1(3) . . . . ? C1TA N3A C2TA N2A -0.6(2) . . . . ? N4A N3A C2TA N2A 180.0(2) . . . . ? C1TB N1B N2B C2TB -0.1(3) . . . . ? C1TB N3B N4B C14B 162.1(2) . . . . ? C2TB N3B N4B C14B -20.9(3) . . . . ? C6B C1B C2B C3B -2.0(3) . . . . ? C14B C1B C2B C3B 172.46(18) . . . . ? C6B C1B C2B N5B 176.58(18) . . . . ? C14B C1B C2B N5B -9.0(3) . . . . ? O1B N5B C2B C3B 145.3(2) . . . . ? O2B N5B C2B C3B -35.2(3) . . . . ? O1B N5B C2B C1B -33.3(3) . . . . ? O2B N5B C2B C1B 146.2(2) . . . . ? C1B C2B C3B C4B 1.2(3) . . . . ? N5B C2B C3B C4B -177.39(19) . . . . ? C2B C3B C4B C5B 0.6(3) . . . . ? C2B C3B C4B N6B -178.63(19) . . . . ? O3B N6B C4B C3B -0.9(3) . . . . ? O4B N6B C4B C3B -179.6(2) . . . . ? O3B N6B C4B C5B 179.8(2) . . . . ? O4B N6B C4B C5B 1.2(3) . . . . ? C3B C4B C5B C6B -1.5(4) . . . . ? N6B C4B C5B C6B 177.7(2) . . . . ? C4B C5B C6B C1B 0.6(3) . . . . ? C2B C1B C6B C5B 1.0(3) . . . . ? C14B C1B C6B C5B -173.51(19) . . . . ? N3B N4B C14B C1B 174.03(16) . . . . ? C6B C1B C14B N4B -32.2(3) . . . . ? C2B C1B C14B N4B 153.5(2) . . . . ? N2B N1B C1TB N3B -0.2(3) . . . . ? C2TB N3B C1TB N1B 0.3(3) . . . . ? N4B N3B C1TB N1B 177.98(19) . . . . ? N1B N2B C2TB N3B 0.2(3) . . . . ? C1TB N3B C2TB N2B -0.3(3) . . . . ? N4B N3B C2TB N2B -177.76(19) . . . . ? _diffrn_measured_fraction_theta_max 0.952 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.184 _refine_diff_density_min -0.163 _refine_diff_density_rms 0.035 # end Validation Reply Form data_2a _database_code_depnum_ccdc_archive 'CCDC 751224' #TrackingRef '- 17.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N-(3-nitrobenzylidene)-4H-1,2,4-triazole-4-amine ; _chemical_name_common N-(3-nitrobenzylidene)-4H-1,2,4-triazole-4-amine _chemical_melting_point ? _chemical_formula_moiety 'C9 H7 N5 O2' _chemical_formula_sum 'C9 H7 N5 O2' _chemical_formula_weight 217.20 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 P21/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 3.870(2) _cell_length_b 10.917(4) _cell_length_c 23.019(7) _cell_angle_alpha 90.00 _cell_angle_beta 94.18(3) _cell_angle_gamma 90.00 _cell_volume 969.9(7) _cell_formula_units_Z 4 _cell_measurement_temperature 230(2) _cell_measurement_reflns_used 2367 _cell_measurement_theta_min 3.25 _cell_measurement_theta_max 28.77 _exptl_crystal_description needles _exptl_crystal_colour colorless _exptl_crystal_size_max 0.59 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.487 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.112 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 230(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 KM4-CCD _diffrn_measurement_method /w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8490 _diffrn_reflns_av_R_equivalents 0.0296 _diffrn_reflns_av_sigmaI/netI 0.0340 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 3.25 _diffrn_reflns_theta_max 28.77 _reflns_number_total 2367 _reflns_number_gt 1430 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.0540P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2367 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0807 _refine_ls_R_factor_gt 0.0422 _refine_ls_wR_factor_ref 0.1053 _refine_ls_wR_factor_gt 0.0964 _refine_ls_goodness_of_fit_ref 0.966 _refine_ls_restrained_S_all 0.966 _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 O1 O 0.5087(4) -0.00873(11) 0.36750(7) 0.0859(5) Uani 1 1 d . . . O2 O 0.2294(4) -0.03968(12) 0.44207(6) 0.0861(5) Uani 1 1 d . . . N1 N 0.9548(4) 0.79139(12) 0.26727(6) 0.0513(4) Uani 1 1 d . . . N2 N 1.0370(4) 0.69073(12) 0.23370(6) 0.0470(4) Uani 1 1 d . . . N3 N 0.7881(3) 0.62484(10) 0.30974(5) 0.0359(3) Uani 1 1 d . . . N4 N 0.6460(3) 0.55626(11) 0.35306(5) 0.0383(3) Uani 1 1 d . . . N5 N 0.3673(4) 0.02812(12) 0.40908(6) 0.0507(4) Uani 1 1 d . . . C1 C 0.4830(4) 0.36144(13) 0.38807(6) 0.0327(3) Uani 1 1 d . . . C2 C 0.4879(4) 0.23673(13) 0.37873(6) 0.0341(3) Uani 1 1 d . . . H2 H 0.5749 0.2044 0.3449 0.041 Uiso 1 1 calc R . . C3 C 0.3630(4) 0.16071(13) 0.41996(6) 0.0365(4) Uani 1 1 d . . . C4 C 0.2350(4) 0.20333(14) 0.47048(6) 0.0429(4) Uani 1 1 d . . . H4 H 0.1519 0.1491 0.4979 0.051 Uiso 1 1 calc R . . C5 C 0.2328(4) 0.32772(15) 0.47941(6) 0.0446(4) Uani 1 1 d . . . H5 H 0.1482 0.3593 0.5136 0.054 Uiso 1 1 calc R . . C6 C 0.3534(4) 0.40695(14) 0.43875(6) 0.0391(4) Uani 1 1 d . . . H6 H 0.3480 0.4919 0.4452 0.047 Uiso 1 1 calc R . . C14 C 0.6216(4) 0.44201(13) 0.34469(6) 0.0353(4) Uani 1 1 d . . . H14 H 0.6938 0.4083 0.3100 0.042 Uiso 1 1 calc R . . C1T C 0.8104(4) 0.74825(14) 0.31205(7) 0.0480(4) Uani 1 1 d . . . H1T H 0.7316 0.7965 0.3422 0.058 Uiso 1 1 calc R . . C2T C 0.9338(4) 0.59333(14) 0.25967(6) 0.0399(4) Uani 1 1 d . . . H2T H 0.9562 0.5128 0.2460 0.048 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 O1 0.1285(13) 0.0361(7) 0.1000(11) -0.0017(7) 0.0559(10) 0.0084(8) O2 0.1238(13) 0.0470(8) 0.0926(11) 0.0120(7) 0.0417(9) -0.0261(8) N1 0.0617(9) 0.0366(8) 0.0572(9) 0.0065(6) 0.0149(7) -0.0032(7) N2 0.0544(9) 0.0413(8) 0.0464(8) 0.0066(6) 0.0105(6) -0.0023(7) N3 0.0417(7) 0.0296(7) 0.0372(7) 0.0023(5) 0.0087(5) 0.0010(5) N4 0.0462(8) 0.0315(7) 0.0385(7) 0.0036(5) 0.0119(6) 0.0006(6) N5 0.0568(10) 0.0378(8) 0.0584(9) 0.0077(7) 0.0099(8) -0.0024(7) C1 0.0323(8) 0.0338(8) 0.0322(7) 0.0006(6) 0.0030(6) 0.0015(6) C2 0.0362(8) 0.0336(8) 0.0330(7) 0.0013(6) 0.0069(6) 0.0012(6) C3 0.0363(9) 0.0327(9) 0.0407(8) 0.0035(6) 0.0039(7) -0.0014(6) C4 0.0415(9) 0.0483(10) 0.0397(9) 0.0098(7) 0.0089(7) -0.0052(8) C5 0.0436(10) 0.0557(11) 0.0359(8) -0.0025(7) 0.0124(7) 0.0003(8) C6 0.0408(8) 0.0371(8) 0.0397(8) -0.0034(7) 0.0053(7) 0.0005(7) C14 0.0401(9) 0.0328(8) 0.0335(8) -0.0002(6) 0.0053(6) 0.0017(7) C1T 0.0615(11) 0.0299(9) 0.0544(10) -0.0002(7) 0.0150(8) 0.0012(8) C2T 0.0465(9) 0.0351(8) 0.0387(8) 0.0013(7) 0.0081(7) 0.0010(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 O1 N5 1.2058(17) . ? O2 N5 1.2118(16) . ? N1 C1T 1.296(2) . ? N1 N2 1.3936(18) . ? N2 C2T 1.2970(18) . ? N3 C1T 1.3508(18) . ? N3 C2T 1.3638(18) . ? N3 N4 1.3918(15) . ? N4 C14 1.2645(19) . ? N5 C3 1.469(2) . ? C1 C2 1.379(2) . ? C1 C6 1.3945(19) . ? C1 C14 1.4617(18) . ? C2 C3 1.3748(18) . ? C2 H2 0.9400 . ? C3 C4 1.378(2) . ? C4 C5 1.374(2) . ? C4 H4 0.9400 . ? C5 C6 1.380(2) . ? C5 H5 0.9400 . ? C6 H6 0.9400 . ? C14 H14 0.9400 . ? C1T H1T 0.9400 . ? C2T H2T 0.9400 . ? 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 C1T N1 N2 106.47(13) . . ? C2T N2 N1 107.49(12) . . ? C1T N3 C2T 104.81(13) . . ? C1T N3 N4 122.40(12) . . ? C2T N3 N4 132.78(12) . . ? C14 N4 N3 116.78(12) . . ? O1 N5 O2 122.67(15) . . ? O1 N5 C3 118.38(13) . . ? O2 N5 C3 118.95(14) . . ? C2 C1 C6 119.48(13) . . ? C2 C1 C14 118.54(13) . . ? C6 C1 C14 121.97(14) . . ? C3 C2 C1 118.61(13) . . ? C3 C2 H2 120.7 . . ? C1 C2 H2 120.7 . . ? C2 C3 C4 123.02(14) . . ? C2 C3 N5 117.92(13) . . ? C4 C3 N5 119.06(13) . . ? C5 C4 C3 117.82(14) . . ? C5 C4 H4 121.1 . . ? C3 C4 H4 121.1 . . ? C4 C5 C6 120.79(14) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C5 C6 C1 120.27(15) . . ? C5 C6 H6 119.9 . . ? C1 C6 H6 119.9 . . ? N4 C14 C1 121.10(13) . . ? N4 C14 H14 119.4 . . ? C1 C14 H14 119.4 . . ? N1 C1T N3 111.17(14) . . ? N1 C1T H1T 124.4 . . ? N3 C1T H1T 124.4 . . ? N2 C2T N3 110.05(14) . . ? N2 C2T H2T 125.0 . . ? N3 C2T H2T 125.0 . . ? 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 C1T N1 N2 C2T 0.82(17) . . . . ? C1T N3 N4 C14 176.27(14) . . . . ? C2T N3 N4 C14 -5.2(2) . . . . ? C6 C1 C2 C3 0.2(2) . . . . ? C14 C1 C2 C3 178.92(13) . . . . ? C1 C2 C3 C4 -0.5(2) . . . . ? C1 C2 C3 N5 179.48(13) . . . . ? O1 N5 C3 C2 6.8(2) . . . . ? O2 N5 C3 C2 -173.21(15) . . . . ? O1 N5 C3 C4 -173.28(16) . . . . ? O2 N5 C3 C4 6.7(2) . . . . ? C2 C3 C4 C5 0.2(2) . . . . ? N5 C3 C4 C5 -179.75(14) . . . . ? C3 C4 C5 C6 0.4(2) . . . . ? C4 C5 C6 C1 -0.7(2) . . . . ? C2 C1 C6 C5 0.4(2) . . . . ? C14 C1 C6 C5 -178.33(13) . . . . ? N3 N4 C14 C1 178.67(12) . . . . ? C2 C1 C14 N4 -174.92(14) . . . . ? C6 C1 C14 N4 3.8(2) . . . . ? N2 N1 C1T N3 -0.79(19) . . . . ? C2T N3 C1T N1 0.47(19) . . . . ? N4 N3 C1T N1 179.37(13) . . . . ? N1 N2 C2T N3 -0.55(17) . . . . ? C1T N3 C2T N2 0.08(17) . . . . ? N4 N3 C2T N2 -178.66(13) . . . . ? _diffrn_measured_fraction_theta_max 0.938 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.201 _refine_diff_density_min -0.179 _refine_diff_density_rms 0.035