data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Prof Roland Boese' _publ_contact_author_address ; Inst. f. Anorg. Chemie University of Essen Universitaetsstr. 3 Essen 45117 GERMANY ; _publ_contact_author_email boese@structchem.uni-essen.de _publ_contact_author_phone '0049 201 183 2416' _publ_contact_author_fax '0049 201 183 2535' _publ_section_title ; Investigations on the structure of 4-methyl-dihydro-1,3,4-benzotriazepin-5-ones. Tautomer reassignment. ; loop_ _publ_author_name _publ_author_address R.Boese ; Institut fur Anorganische Chemie der Universitat-GH Essen Universitatsstr. 3-5 D-45117 Essen, Germany ; J.A.Zahra ; Chemistry Department Faculty of Science University of Jordan Amman, Jordan ; M.M.El-Abadelah ; Chemistry Department Faculty of Science University of Jordan Amman, Jordan ; M.Z.Nazer ; Chemistry Department Faculty of Science University of Jordan Amman, Jordan ; K.A.K.Ebraheem ; Chemistry Department Faculty of Science University of Petra Amman, Jordan ; data_tauaba0m _database_code_CSD 200677 _ccdc_compound_id 2a _refine_ls_abs_structure_details ? _ccdc_disorder ? _ccdc_comments ? _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-Methyl-dihydro-1,3,4-benzotriazepin-5-ones ; _chemical_name_common 4-Methyl-dihydro-1,3,4-benzotriazepin-5-ones _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H9 N3 O' _chemical_formula_weight 175.19 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 P2(1)/c 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 16.906(8) _cell_length_b 14.087(7) _cell_length_c 7.001(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.368(10) _cell_angle_gamma 90.00 _cell_volume 1667.3(14) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3000 _cell_measurement_theta_min 2.81 _cell_measurement_theta_max 28.30 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.396 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.48 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details ; Siemens SADABS program multi-scan V2.03 R.H. Blessing, Acta Cryst. (1995) A51 33-38 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens SMART CCD area detector system' _diffrn_measurement_method ; Fullsphere data collection in omega at 0.3 deg scan width, two runs with 720 frames, phi = 0, 270(deg) two runs with 436 frames, phi = 88, 180 deg) ; _diffrn_detector_area_resol_mean 512 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9461 _diffrn_reflns_av_R_equivalents 0.0677 _diffrn_reflns_av_sigmaI/netI 0.0805 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2925 _reflns_number_gt 1950 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER AXS SMART Vers. 5.054 1997/98' _computing_cell_refinement 'BRUKER AXS SAINT program Vers.6.01' _computing_data_reduction 'BRUKER AXS SAINT program Vers.6.01' _computing_structure_solution 'BRUKER AXS SHELXTL Vers.6.12,98/NT/2000/ME' _computing_structure_refinement 'BRUKER AXS SHELXTL Vers.6.12,98/NT/2000/ME' _computing_molecular_graphics 'BRUKER AXS SHELXTL Vers.6.12,98/NT/2000/ME' _computing_publication_material 'BRUKER AXS SHELXTL Vers.6.12,98/NT/2000/ME' _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^)+(0.1289P)^2^+0.0192P] 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 ; Riding model on idealized geometries with the 1.2 fold (1.5 fold for methyl groups) isotropic displacement parameters of the equivalent Uij of the corresponding carbon atom; nitrogen hydrogen atom positions taken from a Fourier-map and also refined as riding group with the 1.2 fold isotropic displacement parameters of the equivalent Uij of the corresponding nitrogen atom. ; _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2925 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1032 _refine_ls_R_factor_gt 0.0714 _refine_ls_wR_factor_ref 0.2077 _refine_ls_wR_factor_gt 0.1812 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _refine_ls_shift/su_max 0.003 _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 N1 N 0.50022(13) 0.73924(15) 0.2664(3) 0.0379(6) Uani 1 1 d . . . H1 H 0.4916 0.6820 0.2670 0.045 Uiso 1 1 d R . . O1 O 0.50658(13) 1.04008(13) 0.2795(3) 0.0536(7) Uani 1 1 d . . . C2 C 0.57267(17) 0.7552(2) 0.1873(4) 0.0402(7) Uani 1 1 d . . . H2 H 0.5964 0.7013 0.1309 0.048 Uiso 1 1 d R . . N3 N 0.61334(14) 0.83115(16) 0.1782(4) 0.0434(7) Uani 1 1 d . . . N4 N 0.58524(14) 0.91207(15) 0.2765(3) 0.0386(6) Uani 1 1 d . . . C5A C 0.44130(16) 0.89666(18) 0.2083(4) 0.0330(7) Uani 1 1 d . . . C5 C 0.51325(17) 0.95425(19) 0.2511(4) 0.0368(7) Uani 1 1 d . . . C6 C 0.37173(17) 0.9476(2) 0.1644(4) 0.0423(8) Uani 1 1 d . . . H6 H 0.3756 1.0137 0.1413 0.051 Uiso 1 1 d R . . C7 C 0.29897(18) 0.9043(2) 0.1527(5) 0.0485(8) Uani 1 1 d . . . H7 H 0.2530 0.9402 0.1232 0.058 Uiso 1 1 d R . . C8 C 0.29342(18) 0.8082(2) 0.1883(5) 0.0484(8) Uani 1 1 d . . . H8 H 0.2434 0.7780 0.1838 0.058 Uiso 1 1 d R . . C9A C 0.43487(15) 0.79909(18) 0.2338(4) 0.0324(7) Uani 1 1 d . . . C9 C 0.36017(17) 0.7563(2) 0.2264(4) 0.0420(8) Uani 1 1 d . . . H9 H 0.3558 0.6902 0.2497 0.050 Uiso 1 1 d R . . C10 C 0.65171(19) 0.9720(2) 0.3354(5) 0.0496(8) Uani 1 1 d . . . H10A H 0.6737 1.0008 0.2266 0.074 Uiso 1 1 d R . . H10B H 0.6906 0.9340 0.3972 0.074 Uiso 1 1 d R . . H10C H 0.6344 1.0198 0.4198 0.074 Uiso 1 1 d R . . O11 O 0.00531(14) 0.39250(17) 0.0660(3) 0.0577(7) Uani 1 1 d . . . N11 N -0.00747(15) 0.39048(18) -0.5351(4) 0.0469(7) Uani 1 1 d . . . H11 H -0.0018 0.4008 -0.6487 0.056 Uiso 1 1 d R . . C12 C -0.07777(19) 0.3462(2) -0.4926(5) 0.0455(8) Uani 1 1 d . . . H12 H -0.1047 0.3190 -0.5984 0.055 Uiso 1 1 d R . . N13 N -0.11240(15) 0.33512(18) -0.3360(4) 0.0486(7) Uani 1 1 d . . . N14 N -0.08177(14) 0.38447(17) -0.1744(4) 0.0429(7) Uani 1 1 d . . . C15A C 0.06205(17) 0.36312(19) -0.2316(4) 0.0372(7) Uani 1 1 d . . . C15 C -0.00719(18) 0.37854(19) -0.1057(4) 0.0395(7) Uani 1 1 d . . . C16 C 0.13323(19) 0.3436(2) -0.1458(5) 0.0478(8) Uani 1 1 d . . . H16 H 0.1340 0.3299 -0.0139 0.057 Uiso 1 1 d R . . C17 C 0.2041(2) 0.3420(2) -0.2425(6) 0.0593(10) Uani 1 1 d . . . H17 H 0.2521 0.3242 -0.1806 0.071 Uiso 1 1 d R . . C18 C 0.2033(2) 0.3658(2) -0.4336(6) 0.0628(11) Uani 1 1 d . . . H18 H 0.2512 0.3693 -0.5010 0.075 Uiso 1 1 d R . . C19A C 0.06129(18) 0.38101(19) -0.4282(4) 0.0394(7) Uani 1 1 d . . . C19 C 0.1326(2) 0.3858(2) -0.5260(5) 0.0521(9) Uani 1 1 d . . . H19 H 0.1322 0.4029 -0.6562 0.062 Uiso 1 1 d R . . C20 C -0.14592(19) 0.4059(2) -0.0430(5) 0.0566(9) Uani 1 1 d . . . H20A H -0.1549 0.3529 0.0365 0.085 Uiso 1 1 d R . . H20B H -0.1926 0.4199 -0.1137 0.085 Uiso 1 1 d R . . H20C H -0.1317 0.4591 0.0327 0.085 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0372(13) 0.0219(11) 0.0547(16) 0.0057(10) 0.0105(12) 0.0015(9) O1 0.0637(14) 0.0233(10) 0.0740(16) -0.0021(10) 0.0171(12) -0.0036(9) C2 0.0393(16) 0.0329(15) 0.0486(19) -0.0061(13) 0.0096(14) 0.0068(12) N3 0.0396(14) 0.0408(13) 0.0499(16) -0.0065(12) 0.0149(12) 0.0029(11) N4 0.0392(14) 0.0323(12) 0.0444(15) -0.0057(11) 0.0119(11) -0.0049(10) C5A 0.0365(15) 0.0280(14) 0.0346(16) 0.0004(11) 0.0147(12) 0.0033(11) C5 0.0470(17) 0.0286(14) 0.0352(16) 0.0041(12) 0.0183(13) -0.0016(12) C6 0.0506(19) 0.0331(14) 0.0434(18) 0.0019(13) 0.0180(14) 0.0096(13) C7 0.0345(17) 0.0506(18) 0.060(2) 0.0011(16) 0.0138(15) 0.0115(14) C8 0.0363(16) 0.0526(19) 0.057(2) -0.0044(16) 0.0139(15) -0.0020(14) C9A 0.0362(15) 0.0283(13) 0.0328(15) -0.0011(11) 0.0149(12) 0.0017(11) C9 0.0425(17) 0.0337(15) 0.0500(19) -0.0012(13) 0.0196(14) -0.0056(13) C10 0.0525(19) 0.0436(17) 0.053(2) -0.0028(15) 0.0066(16) -0.0098(14) O11 0.0668(16) 0.0711(15) 0.0353(14) -0.0020(11) 0.0120(12) 0.0010(12) N11 0.0572(17) 0.0505(15) 0.0332(14) 0.0041(11) 0.0090(13) -0.0060(12) C12 0.0499(19) 0.0419(17) 0.045(2) 0.0001(14) 0.0031(16) -0.0044(14) N13 0.0389(14) 0.0513(15) 0.0556(18) -0.0050(13) 0.0078(13) -0.0066(11) N14 0.0404(14) 0.0445(14) 0.0440(16) -0.0014(12) 0.0129(12) -0.0004(11) C15A 0.0405(17) 0.0307(14) 0.0405(18) 0.0025(13) 0.0115(14) -0.0012(11) C15 0.0478(19) 0.0344(15) 0.0365(18) 0.0014(13) 0.0081(14) -0.0014(13) C16 0.0494(19) 0.0427(17) 0.051(2) -0.0053(14) 0.0028(16) -0.0021(14) C17 0.0402(19) 0.0479(19) 0.090(3) -0.0093(19) 0.0079(19) -0.0005(14) C18 0.051(2) 0.0520(19) 0.085(3) -0.014(2) 0.035(2) -0.0131(16) C19A 0.0479(18) 0.0311(14) 0.0394(17) -0.0016(13) 0.0134(14) -0.0044(13) C19 0.061(2) 0.0471(18) 0.048(2) -0.0029(15) 0.0310(17) -0.0118(15) C20 0.050(2) 0.056(2) 0.064(2) -0.0064(17) 0.0259(17) 0.0048(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C2 1.366(4) . ? N1 C9A 1.407(3) . ? O1 C5 1.231(3) . ? C2 N3 1.274(4) . ? N3 N4 1.415(3) . ? N4 C5 1.365(4) . ? N4 C10 1.463(4) . ? C5A C9A 1.390(4) . ? C5A C6 1.410(4) . ? C5A C5 1.491(4) . ? C6 C7 1.375(4) . ? C7 C8 1.380(4) . ? C8 C9 1.370(4) . ? C9A C9 1.400(4) . ? O11 C15 1.235(4) . ? N11 C12 1.377(4) . ? N11 C19A 1.385(4) . ? C12 N13 1.255(4) . ? N13 N14 1.423(4) . ? N14 C15 1.349(4) . ? N14 C20 1.458(4) . ? C15A C16 1.370(4) . ? C15A C19A 1.399(4) . ? C15A C15 1.486(4) . ? C16 C17 1.381(5) . ? C17 C18 1.379(5) . ? C18 C19 1.383(5) . ? C19A C19 1.393(4) . ? 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 C2 N1 C9A 122.7(2) . . ? N3 C2 N1 130.1(3) . . ? C2 N3 N4 118.0(2) . . ? C5 N4 N3 126.1(2) . . ? C5 N4 C10 117.9(2) . . ? N3 N4 C10 110.0(2) . . ? C9A C5A C6 117.7(3) . . ? C9A C5A C5 125.2(2) . . ? C6 C5A C5 116.4(2) . . ? O1 C5 N4 119.3(3) . . ? O1 C5 C5A 119.4(2) . . ? N4 C5 C5A 121.0(2) . . ? C7 C6 C5A 122.2(3) . . ? C6 C7 C8 119.1(3) . . ? C9 C8 C7 120.2(3) . . ? C5A C9A C9 119.5(2) . . ? C5A C9A N1 123.5(2) . . ? C9 C9A N1 117.0(2) . . ? C8 C9 C9A 121.2(3) . . ? C12 N11 C19A 124.2(3) . . ? N13 C12 N11 130.8(3) . . ? C12 N13 N14 117.7(3) . . ? C15 N14 N13 126.0(2) . . ? C15 N14 C20 119.0(3) . . ? N13 N14 C20 109.6(2) . . ? C16 C15A C19A 118.1(3) . . ? C16 C15A C15 117.5(3) . . ? C19A C15A C15 123.7(3) . . ? O11 C15 N14 119.4(3) . . ? O11 C15 C15A 118.0(3) . . ? N14 C15 C15A 122.4(3) . . ? C15A C16 C17 123.4(3) . . ? C18 C17 C16 117.9(3) . . ? C17 C18 C19 120.4(3) . . ? N11 C19A C19 117.1(3) . . ? N11 C19A C15A 123.5(3) . . ? C19 C19A C15A 119.3(3) . . ? C18 C19 C19A 120.5(3) . . ? 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 C9A N1 C2 N3 47.3(5) . . . . ? N1 C2 N3 N4 6.1(5) . . . . ? C2 N3 N4 C5 -57.3(4) . . . . ? C2 N3 N4 C10 150.8(3) . . . . ? N3 N4 C5 O1 -150.4(3) . . . . ? C10 N4 C5 O1 -0.5(4) . . . . ? N3 N4 C5 C5A 35.6(4) . . . . ? C10 N4 C5 C5A -174.5(3) . . . . ? C9A C5A C5 O1 -158.0(3) . . . . ? C6 C5A C5 O1 12.6(4) . . . . ? C9A C5A C5 N4 15.9(4) . . . . ? C6 C5A C5 N4 -173.4(3) . . . . ? C9A C5A C6 C7 2.2(4) . . . . ? C5 C5A C6 C7 -169.2(3) . . . . ? C5A C6 C7 C8 1.1(5) . . . . ? C6 C7 C8 C9 -2.8(5) . . . . ? C6 C5A C9A C9 -3.8(4) . . . . ? C5 C5A C9A C9 166.8(3) . . . . ? C6 C5A C9A N1 176.0(3) . . . . ? C5 C5A C9A N1 -13.5(4) . . . . ? C2 N1 C9A C5A -33.8(4) . . . . ? C2 N1 C9A C9 145.9(3) . . . . ? C7 C8 C9 C9A 1.2(5) . . . . ? C5A C9A C9 C8 2.2(4) . . . . ? N1 C9A C9 C8 -177.5(3) . . . . ? C19A N11 C12 N13 43.3(5) . . . . ? N11 C12 N13 N14 8.7(5) . . . . ? C12 N13 N14 C15 -56.6(4) . . . . ? C12 N13 N14 C20 150.0(3) . . . . ? N13 N14 C15 O11 -152.0(3) . . . . ? C20 N14 C15 O11 -0.9(4) . . . . ? N13 N14 C15 C15A 32.9(4) . . . . ? C20 N14 C15 C15A -176.0(3) . . . . ? C16 C15A C15 O11 14.7(4) . . . . ? C19A C15A C15 O11 -155.5(3) . . . . ? C16 C15A C15 N14 -170.1(3) . . . . ? C19A C15A C15 N14 19.6(4) . . . . ? C19A C15A C16 C17 1.0(4) . . . . ? C15 C15A C16 C17 -169.8(3) . . . . ? C15A C16 C17 C18 3.2(5) . . . . ? C16 C17 C18 C19 -3.2(5) . . . . ? C12 N11 C19A C19 147.9(3) . . . . ? C12 N11 C19A C15A -29.3(4) . . . . ? C16 C15A C19A N11 172.1(3) . . . . ? C15 C15A C19A N11 -17.7(4) . . . . ? C16 C15A C19A C19 -5.0(4) . . . . ? C15 C15A C19A C19 165.2(3) . . . . ? C17 C18 C19 C19A -0.8(5) . . . . ? N11 C19A C19 C18 -172.3(3) . . . . ? C15A C19A C19 C18 5.0(4) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.382 _refine_diff_density_min -0.264 _refine_diff_density_rms 0.076