# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Sundeep Rayat' 'Olajide Alawode' 'John Desper' _publ_contact_author_name 'Sundeep Rayat' _publ_contact_author_address ; Department of Chemistry 213 CBC Building Kansas State University Manhattan, KS 66506-0401 USA ; _publ_contact_author_email SUNDEEP@KSU.EDU _publ_section_title ; Intermolecular interactions in the crystal structures of substituted tetrazolones ; # Attachment 'allXray.cif' data_oa0701m _database_code_depnum_ccdc_archive 'CCDC 714340' _audit_creation_method SHELXL-97 _chemical_name_systematic ; HG-I1 N-(m-methoxyphenyl)tetrazolone ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; C8 H8 N4 O2 ; _chemical_formula_sum 'C8 H8 N4 O2' _chemical_formula_weight 192.18 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 12.414(11) _cell_length_b 19.068(16) _cell_length_c 7.190(6) _cell_angle_alpha 90.00 _cell_angle_beta 99.28(2) _cell_angle_gamma 90.00 _cell_volume 1680(2) _cell_formula_units_Z 8 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 4682 _cell_measurement_theta_min 2.71 _cell_measurement_theta_max 32.25 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.520 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.114 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26044 _diffrn_reflns_av_R_equivalents 0.0610 _diffrn_reflns_av_sigmaI/netI 0.0563 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 33.60 _reflns_number_total 6508 _reflns_number_gt 3772 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0900P)^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 6508 _refine_ls_number_parameters 259 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0997 _refine_ls_R_factor_gt 0.0533 _refine_ls_wR_factor_ref 0.1707 _refine_ls_wR_factor_gt 0.1435 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _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 N11_1 N 0.58202(8) 0.27149(5) 0.28509(15) 0.0284(2) Uani 1 1 d . . . N12_1 N 0.49816(10) 0.31342(6) 0.20502(16) 0.0356(3) Uani 1 1 d . . . N13_1 N 0.52788(10) 0.37630(6) 0.23570(17) 0.0395(3) Uani 1 1 d . . . N14_1 N 0.62954(10) 0.37639(6) 0.33446(16) 0.0347(3) Uani 1 1 d . . . H14_1 H 0.6652(13) 0.4168(9) 0.375(2) 0.042 Uiso 1 1 d . . . C15_1 C 0.66785(11) 0.31135(6) 0.37184(18) 0.0293(3) Uani 1 1 d . . . O15_1 O 0.75581(8) 0.29280(5) 0.46115(15) 0.0390(2) Uani 1 1 d . . . C21_1 C 0.64290(11) 0.08487(6) 0.35410(18) 0.0309(3) Uani 1 1 d . . . O21_1 O 0.73052(8) 0.04844(5) 0.44315(16) 0.0429(3) Uani 1 1 d . . . C22_1 C 0.65604(11) 0.15667(6) 0.35876(18) 0.0303(3) Uani 1 1 d . . . H22_1 H 0.7225 0.1772 0.4179 0.036 Uiso 1 1 calc R . . C23_1 C 0.57072(10) 0.19796(6) 0.27585(17) 0.0263(2) Uani 1 1 d . . . C24_1 C 0.47309(11) 0.16932(7) 0.18526(19) 0.0336(3) Uani 1 1 d . . . H24_1 H 0.4149 0.1985 0.1284 0.040 Uiso 1 1 calc R . . C25_1 C 0.46351(12) 0.09807(7) 0.1806(2) 0.0389(3) Uani 1 1 d . . . H25_1 H 0.3978 0.0775 0.1181 0.047 Uiso 1 1 calc R . . C26_1 C 0.54720(11) 0.05482(7) 0.2648(2) 0.0355(3) Uani 1 1 d . . . H26_1 H 0.5388 0.0053 0.2611 0.043 Uiso 1 1 calc R . . C27_1 C 0.71757(13) -0.02449(7) 0.4646(2) 0.0445(4) Uani 1 1 d . . . H27A_1 H 0.7859 -0.0446 0.5304 0.067 Uiso 1 1 calc R . . H27B_1 H 0.6989 -0.0463 0.3401 0.067 Uiso 1 1 calc R . . H27C_1 H 0.6589 -0.0332 0.5380 0.067 Uiso 1 1 calc R . . N11_2 N 0.92496(9) 0.50782(5) 0.67779(15) 0.0296(2) Uani 1 1 d . . . N12_2 N 1.00518(10) 0.46592(6) 0.77011(17) 0.0390(3) Uani 1 1 d . . . N13_2 N 0.97721(10) 0.40321(6) 0.73563(18) 0.0400(3) Uani 1 1 d . . . N14_2 N 0.87958(9) 0.40262(5) 0.62272(16) 0.0340(3) Uani 1 1 d . . . H14_2 H 0.8408(14) 0.3607(9) 0.574(2) 0.041 Uiso 1 1 d . . . C15_2 C 0.84292(11) 0.46791(6) 0.58146(18) 0.0308(3) Uani 1 1 d . . . O15_2 O 0.75756(9) 0.48614(5) 0.48175(16) 0.0453(3) Uani 1 1 d . . . C21_2 C 0.86212(11) 0.69495(6) 0.62067(18) 0.0296(3) Uani 1 1 d . . . O21_2 O 0.77412(8) 0.73163(5) 0.53551(15) 0.0429(3) Uani 1 1 d . . . C22_2 C 0.85143(11) 0.62309(6) 0.60616(18) 0.0310(3) Uani 1 1 d . . . H22_2 H 0.7869 0.6027 0.5387 0.037 Uiso 1 1 calc R . . C23_2 C 0.93564(10) 0.58136(6) 0.69094(16) 0.0275(2) Uani 1 1 d . . . C24_2 C 1.03151(11) 0.60959(7) 0.78931(19) 0.0340(3) Uani 1 1 d . . . H24_2 H 1.0890 0.5802 0.8474 0.041 Uiso 1 1 calc R . . C25_2 C 1.04024(12) 0.68104(7) 0.7997(2) 0.0363(3) Uani 1 1 d . . . H25_2 H 1.1052 0.7013 0.8659 0.044 Uiso 1 1 calc R . . C26_2 C 0.95704(11) 0.72468(7) 0.71625(19) 0.0341(3) Uani 1 1 d . . . H26_2 H 0.9649 0.7742 0.7244 0.041 Uiso 1 1 calc R . . C27_2 C 0.77595(13) 0.80514(7) 0.5602(2) 0.0407(3) Uani 1 1 d . . . H27A_2 H 0.7082 0.8254 0.4926 0.061 Uiso 1 1 calc R . . H27B_2 H 0.8384 0.8249 0.5104 0.061 Uiso 1 1 calc R . . H27C_2 H 0.7825 0.8161 0.6947 0.061 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 N11_1 0.0291(5) 0.0183(5) 0.0354(5) -0.0008(4) -0.0017(4) 0.0008(4) N12_1 0.0360(6) 0.0229(5) 0.0438(6) 0.0008(4) -0.0061(5) 0.0051(4) N13_1 0.0428(7) 0.0234(5) 0.0480(7) 0.0002(4) -0.0061(5) 0.0050(5) N14_1 0.0369(6) 0.0181(5) 0.0456(6) -0.0013(4) -0.0039(5) 0.0005(4) C15_1 0.0314(6) 0.0194(5) 0.0360(6) -0.0017(4) 0.0026(5) -0.0015(4) O15_1 0.0317(5) 0.0205(4) 0.0596(6) -0.0030(4) -0.0087(4) -0.0001(4) C21_1 0.0292(6) 0.0207(5) 0.0411(7) 0.0007(4) 0.0006(5) 0.0002(4) O21_1 0.0362(5) 0.0186(4) 0.0682(7) 0.0037(4) -0.0095(5) 0.0007(4) C22_1 0.0278(6) 0.0201(6) 0.0406(6) -0.0013(4) -0.0018(5) -0.0020(4) C23_1 0.0281(6) 0.0186(5) 0.0314(6) -0.0012(4) 0.0022(5) -0.0018(4) C24_1 0.0281(6) 0.0262(6) 0.0437(7) -0.0007(5) -0.0026(5) -0.0003(5) C25_1 0.0306(7) 0.0274(7) 0.0545(8) -0.0018(6) -0.0060(6) -0.0064(5) C26_1 0.0336(7) 0.0199(6) 0.0506(8) -0.0028(5) -0.0001(6) -0.0039(5) C27_1 0.0466(9) 0.0199(6) 0.0641(9) 0.0062(6) 0.0004(7) 0.0028(6) N11_2 0.0311(5) 0.0191(5) 0.0363(5) 0.0003(4) -0.0013(4) 0.0005(4) N12_2 0.0387(6) 0.0230(5) 0.0502(7) 0.0014(4) -0.0083(5) 0.0043(5) N13_2 0.0417(7) 0.0246(6) 0.0499(7) -0.0004(5) -0.0038(5) 0.0043(5) N14_2 0.0356(6) 0.0195(5) 0.0448(6) -0.0019(4) 0.0001(5) 0.0011(4) C15_2 0.0329(6) 0.0193(5) 0.0388(6) -0.0011(4) 0.0018(5) -0.0001(5) O15_2 0.0407(6) 0.0204(5) 0.0667(7) -0.0013(4) -0.0164(5) -0.0011(4) C21_2 0.0335(6) 0.0191(5) 0.0334(6) 0.0017(4) -0.0034(5) -0.0020(4) O21_2 0.0435(6) 0.0189(4) 0.0587(6) 0.0017(4) -0.0142(5) -0.0007(4) C22_2 0.0323(6) 0.0205(5) 0.0369(6) -0.0003(4) -0.0044(5) -0.0047(5) C23_2 0.0307(6) 0.0199(5) 0.0309(5) -0.0006(4) 0.0024(5) -0.0031(4) C24_2 0.0308(6) 0.0269(6) 0.0414(7) -0.0002(5) -0.0032(5) -0.0011(5) C25_2 0.0331(7) 0.0269(6) 0.0448(7) -0.0026(5) -0.0059(6) -0.0070(5) C26_2 0.0393(7) 0.0209(6) 0.0393(7) -0.0001(5) -0.0014(6) -0.0063(5) C27_2 0.0480(8) 0.0190(6) 0.0523(8) 0.0007(5) -0.0003(7) 0.0031(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 N11_1 N12_1 1.3643(16) . ? N11_1 C15_1 1.3740(17) . ? N11_1 C23_1 1.4096(18) . ? N12_1 N13_1 1.2634(18) . ? N13_1 N14_1 1.3447(19) . ? N14_1 C15_1 1.3398(18) . ? N14_1 H14_1 0.912(17) . ? C15_1 O15_1 1.2263(18) . ? C21_1 O21_1 1.3606(17) . ? C21_1 C22_1 1.379(2) . ? C21_1 C26_1 1.381(2) . ? O21_1 C27_1 1.4111(19) . ? C22_1 C23_1 1.3761(19) . ? C22_1 H22_1 0.9500 . ? C23_1 C24_1 1.3918(19) . ? C24_1 C25_1 1.364(2) . ? C24_1 H24_1 0.9500 . ? C25_1 C26_1 1.387(2) . ? C25_1 H25_1 0.9500 . ? C26_1 H26_1 0.9500 . ? C27_1 H27A_1 0.9800 . ? C27_1 H27B_1 0.9800 . ? C27_1 H27C_1 0.9800 . ? N11_2 N12_2 1.3629(17) . ? N11_2 C15_2 1.3671(18) . ? N11_2 C23_2 1.4103(19) . ? N12_2 N13_2 1.2586(18) . ? N13_2 N14_2 1.3457(19) . ? N14_2 C15_2 1.3421(18) . ? N14_2 H14_2 0.968(16) . ? C15_2 O15_2 1.2300(18) . ? C21_2 O21_2 1.3571(17) . ? C21_2 C22_2 1.3790(19) . ? C21_2 C26_2 1.3860(19) . ? O21_2 C27_2 1.4126(19) . ? C22_2 C23_2 1.3755(19) . ? C22_2 H22_2 0.9500 . ? C23_2 C24_2 1.3910(19) . ? C24_2 C25_2 1.368(2) . ? C24_2 H24_2 0.9500 . ? C25_2 C26_2 1.385(2) . ? C25_2 H25_2 0.9500 . ? C26_2 H26_2 0.9500 . ? C27_2 H27A_2 0.9800 . ? C27_2 H27B_2 0.9800 . ? C27_2 H27C_2 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N12_1 N11_1 C15_1 110.53(12) . . ? N12_1 N11_1 C23_1 119.97(11) . . ? C15_1 N11_1 C23_1 129.46(11) . . ? N13_1 N12_1 N11_1 107.51(12) . . ? N12_1 N13_1 N14_1 108.43(11) . . ? C15_1 N14_1 N13_1 112.17(11) . . ? C15_1 N14_1 H14_1 125.5(11) . . ? N13_1 N14_1 H14_1 122.3(11) . . ? O15_1 C15_1 N14_1 129.01(12) . . ? O15_1 C15_1 N11_1 129.65(12) . . ? N14_1 C15_1 N11_1 101.34(12) . . ? O21_1 C21_1 C22_1 114.40(12) . . ? O21_1 C21_1 C26_1 124.73(13) . . ? C22_1 C21_1 C26_1 120.86(12) . . ? C21_1 O21_1 C27_1 117.25(11) . . ? C23_1 C22_1 C21_1 118.55(12) . . ? C23_1 C22_1 H22_1 120.7 . . ? C21_1 C22_1 H22_1 120.7 . . ? C22_1 C23_1 C24_1 121.98(12) . . ? C22_1 C23_1 N11_1 119.00(11) . . ? C24_1 C23_1 N11_1 119.01(11) . . ? C25_1 C24_1 C23_1 117.93(12) . . ? C25_1 C24_1 H24_1 121.0 . . ? C23_1 C24_1 H24_1 121.0 . . ? C24_1 C25_1 C26_1 121.70(13) . . ? C24_1 C25_1 H25_1 119.2 . . ? C26_1 C25_1 H25_1 119.2 . . ? C21_1 C26_1 C25_1 118.96(13) . . ? C21_1 C26_1 H26_1 120.5 . . ? C25_1 C26_1 H26_1 120.5 . . ? O21_1 C27_1 H27A_1 109.5 . . ? O21_1 C27_1 H27B_1 109.5 . . ? H27A_1 C27_1 H27B_1 109.5 . . ? O21_1 C27_1 H27C_1 109.5 . . ? H27A_1 C27_1 H27C_1 109.5 . . ? H27B_1 C27_1 H27C_1 109.5 . . ? N12_2 N11_2 C15_2 110.29(12) . . ? N12_2 N11_2 C23_2 119.79(11) . . ? C15_2 N11_2 C23_2 129.93(11) . . ? N13_2 N12_2 N11_2 107.71(12) . . ? N12_2 N13_2 N14_2 108.66(11) . . ? C15_2 N14_2 N13_2 111.47(11) . . ? C15_2 N14_2 H14_2 123.7(10) . . ? N13_2 N14_2 H14_2 124.8(10) . . ? O15_2 C15_2 N14_2 128.36(12) . . ? O15_2 C15_2 N11_2 129.75(12) . . ? N14_2 C15_2 N11_2 101.88(12) . . ? O21_2 C21_2 C22_2 114.66(12) . . ? O21_2 C21_2 C26_2 124.84(12) . . ? C22_2 C21_2 C26_2 120.51(12) . . ? C21_2 O21_2 C27_2 117.33(11) . . ? C23_2 C22_2 C21_2 118.96(12) . . ? C23_2 C22_2 H22_2 120.5 . . ? C21_2 C22_2 H22_2 120.5 . . ? C22_2 C23_2 C24_2 121.90(13) . . ? C22_2 C23_2 N11_2 119.27(11) . . ? C24_2 C23_2 N11_2 118.83(11) . . ? C25_2 C24_2 C23_2 117.83(12) . . ? C25_2 C24_2 H24_2 121.1 . . ? C23_2 C24_2 H24_2 121.1 . . ? C24_2 C25_2 C26_2 121.85(13) . . ? C24_2 C25_2 H25_2 119.1 . . ? C26_2 C25_2 H25_2 119.1 . . ? C25_2 C26_2 C21_2 118.95(13) . . ? C25_2 C26_2 H26_2 120.5 . . ? C21_2 C26_2 H26_2 120.5 . . ? O21_2 C27_2 H27A_2 109.5 . . ? O21_2 C27_2 H27B_2 109.5 . . ? H27A_2 C27_2 H27B_2 109.5 . . ? O21_2 C27_2 H27C_2 109.5 . . ? H27A_2 C27_2 H27C_2 109.5 . . ? H27B_2 C27_2 H27C_2 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C15_1 N11_1 N12_1 N13_1 0.70(15) . . . . ? C23_1 N11_1 N12_1 N13_1 178.78(11) . . . . ? N11_1 N12_1 N13_1 N14_1 -0.05(15) . . . . ? N12_1 N13_1 N14_1 C15_1 -0.63(16) . . . . ? N13_1 N14_1 C15_1 O15_1 -178.47(14) . . . . ? N13_1 N14_1 C15_1 N11_1 0.99(14) . . . . ? N12_1 N11_1 C15_1 O15_1 178.45(14) . . . . ? C23_1 N11_1 C15_1 O15_1 0.6(2) . . . . ? N12_1 N11_1 C15_1 N14_1 -1.01(14) . . . . ? C23_1 N11_1 C15_1 N14_1 -178.85(12) . . . . ? C22_1 C21_1 O21_1 C27_1 172.14(12) . . . . ? C26_1 C21_1 O21_1 C27_1 -7.8(2) . . . . ? O21_1 C21_1 C22_1 C23_1 -178.59(11) . . . . ? C26_1 C21_1 C22_1 C23_1 1.4(2) . . . . ? C21_1 C22_1 C23_1 C24_1 -1.17(19) . . . . ? C21_1 C22_1 C23_1 N11_1 177.99(11) . . . . ? N12_1 N11_1 C23_1 C22_1 -179.53(11) . . . . ? C15_1 N11_1 C23_1 C22_1 -1.86(19) . . . . ? N12_1 N11_1 C23_1 C24_1 -0.35(18) . . . . ? C15_1 N11_1 C23_1 C24_1 177.33(12) . . . . ? C22_1 C23_1 C24_1 C25_1 0.1(2) . . . . ? N11_1 C23_1 C24_1 C25_1 -179.03(12) . . . . ? C23_1 C24_1 C25_1 C26_1 0.8(2) . . . . ? O21_1 C21_1 C26_1 C25_1 179.42(13) . . . . ? C22_1 C21_1 C26_1 C25_1 -0.5(2) . . . . ? C24_1 C25_1 C26_1 C21_1 -0.6(2) . . . . ? C15_2 N11_2 N12_2 N13_2 0.15(16) . . . . ? C23_2 N11_2 N12_2 N13_2 -179.55(12) . . . . ? N11_2 N12_2 N13_2 N14_2 -0.28(16) . . . . ? N12_2 N13_2 N14_2 C15_2 0.32(17) . . . . ? N13_2 N14_2 C15_2 O15_2 179.50(14) . . . . ? N13_2 N14_2 C15_2 N11_2 -0.21(15) . . . . ? N12_2 N11_2 C15_2 O15_2 -179.67(15) . . . . ? C23_2 N11_2 C15_2 O15_2 0.0(2) . . . . ? N12_2 N11_2 C15_2 N14_2 0.04(14) . . . . ? C23_2 N11_2 C15_2 N14_2 179.71(12) . . . . ? C22_2 C21_2 O21_2 C27_2 174.28(12) . . . . ? C26_2 C21_2 O21_2 C27_2 -5.7(2) . . . . ? O21_2 C21_2 C22_2 C23_2 -178.84(11) . . . . ? C26_2 C21_2 C22_2 C23_2 1.2(2) . . . . ? C21_2 C22_2 C23_2 C24_2 -0.6(2) . . . . ? C21_2 C22_2 C23_2 N11_2 179.56(12) . . . . ? N12_2 N11_2 C23_2 C22_2 -176.29(12) . . . . ? C15_2 N11_2 C23_2 C22_2 4.1(2) . . . . ? N12_2 N11_2 C23_2 C24_2 3.85(17) . . . . ? C15_2 N11_2 C23_2 C24_2 -175.79(13) . . . . ? C22_2 C23_2 C24_2 C25_2 -0.1(2) . . . . ? N11_2 C23_2 C24_2 C25_2 179.77(12) . . . . ? C23_2 C24_2 C25_2 C26_2 0.2(2) . . . . ? C24_2 C25_2 C26_2 C21_2 0.4(2) . . . . ? O21_2 C21_2 C26_2 C25_2 178.93(13) . . . . ? C22_2 C21_2 C26_2 C25_2 -1.1(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N14_1 H14_1 O15_2 0.912(17) 1.836(17) 2.736(2) 168.4(16) . N14_2 H14_2 O15_1 0.968(16) 1.782(17) 2.742(2) 170.9(15) . _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 33.60 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.385 _refine_diff_density_min -0.331 _refine_diff_density_rms 0.059 #===END data_oa0802m _database_code_depnum_ccdc_archive 'CCDC 714341' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-(4-methoxyphenyl)-1,5-dihydro-5H-tetrazolone ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H8 N4 O2' _chemical_formula_sum 'C8 H8 N4 O2' _chemical_formula_weight 192.18 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)/n 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 10.1689(3) _cell_length_b 6.9582(2) _cell_length_c 12.1607(4) _cell_angle_alpha 90.00 _cell_angle_beta 104.7990(10) _cell_angle_gamma 90.00 _cell_volume 831.91(4) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 5255 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 33.12 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.534 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 400 _exptl_absorpt_coefficient_mu 0.116 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9747 _diffrn_reflns_av_R_equivalents 0.0167 _diffrn_reflns_av_sigmaI/netI 0.0170 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 33.14 _reflns_number_total 3139 _reflns_number_gt 2760 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0800P)^2^+0.1000P] 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 3139 _refine_ls_number_parameters 131 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0445 _refine_ls_R_factor_gt 0.0399 _refine_ls_wR_factor_ref 0.1205 _refine_ls_wR_factor_gt 0.1148 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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 N11 N 0.26670(6) 0.62031(9) 0.12803(5) 0.01675(13) Uani 1 1 d . . . N12 N 0.16018(6) 0.65394(10) 0.03502(5) 0.02099(14) Uani 1 1 d . . . N13 N 0.20357(7) 0.63548(11) -0.05432(6) 0.02278(15) Uani 1 1 d . . . N14 N 0.33787(6) 0.59200(10) -0.02148(5) 0.02060(14) Uani 1 1 d . . . H14 H 0.3858(12) 0.5622(17) -0.0714(10) 0.025 Uiso 1 1 d . . . C15 C 0.38244(7) 0.57825(10) 0.09385(6) 0.01737(14) Uani 1 1 d . . . O15 O 0.49690(5) 0.53755(9) 0.15220(5) 0.02222(14) Uani 1 1 d . . . C21 C 0.24563(7) 0.61735(10) 0.23922(6) 0.01563(14) Uani 1 1 d . . . C22 C 0.11425(7) 0.58535(11) 0.25065(6) 0.01828(14) Uani 1 1 d . . . H22 H 0.0413 0.5638 0.1853 0.022 Uiso 1 1 calc R . . C23 C 0.09123(7) 0.58536(11) 0.35784(6) 0.01951(15) Uani 1 1 d . . . H23 H 0.0020 0.5643 0.3662 0.023 Uiso 1 1 calc R . . C24 C 0.19866(7) 0.61628(10) 0.45408(6) 0.01738(14) Uani 1 1 d . . . O24 O 0.16287(6) 0.61789(10) 0.55476(5) 0.02392(14) Uani 1 1 d . . . C25 C 0.33011(7) 0.64447(11) 0.44240(6) 0.01798(14) Uani 1 1 d . . . H25 H 0.4035 0.6629 0.5078 0.022 Uiso 1 1 calc R . . C26 C 0.35341(7) 0.64556(10) 0.33411(6) 0.01738(14) Uani 1 1 d . . . H26 H 0.4426 0.6655 0.3254 0.021 Uiso 1 1 calc R . . C27 C 0.26852(9) 0.64091(15) 0.65631(7) 0.02812(18) Uani 1 1 d . . . H27A H 0.2294 0.6401 0.7221 0.042 Uiso 1 1 calc R . . H27B H 0.3152 0.7634 0.6536 0.042 Uiso 1 1 calc R . . H27C H 0.3337 0.5351 0.6632 0.042 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 N11 0.0137(2) 0.0201(3) 0.0162(3) 0.00035(19) 0.00343(19) 0.00128(19) N12 0.0163(3) 0.0278(3) 0.0176(3) 0.0007(2) 0.0020(2) 0.0043(2) N13 0.0170(3) 0.0318(3) 0.0185(3) 0.0011(2) 0.0026(2) 0.0046(2) N14 0.0159(3) 0.0293(3) 0.0163(3) 0.0013(2) 0.0036(2) 0.0033(2) C15 0.0153(3) 0.0201(3) 0.0171(3) 0.0010(2) 0.0049(2) 0.0003(2) O15 0.0145(2) 0.0338(3) 0.0181(2) 0.0017(2) 0.00387(18) 0.00334(19) C21 0.0143(3) 0.0160(3) 0.0171(3) -0.0002(2) 0.0048(2) 0.0004(2) C22 0.0133(3) 0.0214(3) 0.0197(3) -0.0013(2) 0.0034(2) -0.0006(2) C23 0.0140(3) 0.0245(3) 0.0205(3) -0.0006(2) 0.0051(2) -0.0013(2) C24 0.0151(3) 0.0198(3) 0.0177(3) 0.0004(2) 0.0050(2) -0.0004(2) O24 0.0186(3) 0.0368(3) 0.0173(3) -0.0009(2) 0.0064(2) -0.0035(2) C25 0.0140(3) 0.0215(3) 0.0181(3) 0.0000(2) 0.0035(2) -0.0006(2) C26 0.0134(3) 0.0203(3) 0.0184(3) -0.0002(2) 0.0041(2) -0.0009(2) C27 0.0230(3) 0.0433(5) 0.0173(3) 0.0013(3) 0.0038(3) -0.0021(3) _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 N11 N12 1.3717(8) . ? N11 C15 1.3761(9) . ? N11 C21 1.4221(9) . ? N12 N13 1.2792(9) . ? N13 N14 1.3556(9) . ? N14 C15 1.3627(9) . ? N14 H14 0.895(12) . ? C15 O15 1.2315(8) . ? C21 C26 1.3876(10) . ? C21 C22 1.3959(9) . ? C22 C23 1.3819(10) . ? C22 H22 0.9500 . ? C23 C24 1.3987(10) . ? C23 H23 0.9500 . ? C24 O24 1.3635(8) . ? C24 C25 1.3937(10) . ? O24 C27 1.4238(10) . ? C25 C26 1.3963(10) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N12 N11 C15 110.08(6) . . ? N12 N11 C21 120.50(6) . . ? C15 N11 C21 129.22(6) . . ? N13 N12 N11 108.19(6) . . ? N12 N13 N14 108.20(6) . . ? N13 N14 C15 111.35(6) . . ? N13 N14 H14 122.3(8) . . ? C15 N14 H14 125.9(8) . . ? O15 C15 N14 128.77(7) . . ? O15 C15 N11 129.07(7) . . ? N14 C15 N11 102.16(6) . . ? C26 C21 C22 120.83(7) . . ? C26 C21 N11 120.65(6) . . ? C22 C21 N11 118.51(6) . . ? C23 C22 C21 119.40(7) . . ? C23 C22 H22 120.3 . . ? C21 C22 H22 120.3 . . ? C22 C23 C24 120.33(6) . . ? C22 C23 H23 119.8 . . ? C24 C23 H23 119.8 . . ? O24 C24 C25 124.98(7) . . ? O24 C24 C23 114.97(6) . . ? C25 C24 C23 120.05(7) . . ? C24 O24 C27 117.67(6) . . ? C24 C25 C26 119.68(7) . . ? C24 C25 H25 120.2 . . ? C26 C25 H25 120.2 . . ? C21 C26 C25 119.69(6) . . ? C21 C26 H26 120.2 . . ? C25 C26 H26 120.2 . . ? O24 C27 H27A 109.5 . . ? O24 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? O24 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C15 N11 N12 N13 -0.14(9) . . . . ? C21 N11 N12 N13 -175.42(6) . . . . ? N11 N12 N13 N14 -0.63(9) . . . . ? N12 N13 N14 C15 1.21(9) . . . . ? N13 N14 C15 O15 178.45(8) . . . . ? N13 N14 C15 N11 -1.21(8) . . . . ? N12 N11 C15 O15 -178.84(8) . . . . ? C21 N11 C15 O15 -4.09(13) . . . . ? N12 N11 C15 N14 0.81(8) . . . . ? C21 N11 C15 N14 175.57(7) . . . . ? N12 N11 C21 C26 -159.12(7) . . . . ? C15 N11 C21 C26 26.60(11) . . . . ? N12 N11 C21 C22 20.92(9) . . . . ? C15 N11 C21 C22 -153.36(8) . . . . ? C26 C21 C22 C23 1.19(11) . . . . ? N11 C21 C22 C23 -178.85(6) . . . . ? C21 C22 C23 C24 -0.29(11) . . . . ? C22 C23 C24 O24 178.41(7) . . . . ? C22 C23 C24 C25 -0.95(11) . . . . ? C25 C24 O24 C27 -3.17(11) . . . . ? C23 C24 O24 C27 177.50(7) . . . . ? O24 C24 C25 C26 -178.00(7) . . . . ? C23 C24 C25 C26 1.30(11) . . . . ? C22 C21 C26 C25 -0.84(10) . . . . ? N11 C21 C26 C25 179.20(6) . . . . ? C24 C25 C26 C21 -0.41(11) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N14 H14 O15 0.895(12) 1.863(12) 2.7435(8) 167.9(11) 3_665 _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 33.14 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.557 _refine_diff_density_min -0.221 _refine_diff_density_rms 0.054 #===END data_oa0803m _database_code_depnum_ccdc_archive 'CCDC 714342' _audit_creation_method SHELXL-97 _chemical_name_systematic ; HG864A 2-(3-methoxyphenyl)-5-methyl-tetrazolone ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H10 N4 O2' _chemical_formula_sum 'C9 H10 N4 O2' _chemical_formula_weight 206.21 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 Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 8.8329(5) _cell_length_b 13.1354(8) _cell_length_c 16.0027(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1856.69(19) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 5776 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 32.88 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.475 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 0.109 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24903 _diffrn_reflns_av_R_equivalents 0.0594 _diffrn_reflns_av_sigmaI/netI 0.0343 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.55 _diffrn_reflns_theta_max 33.06 _reflns_number_total 3437 _reflns_number_gt 2672 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0725P)^2^+0.1000P] 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 3437 _refine_ls_number_parameters 138 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0567 _refine_ls_R_factor_gt 0.0410 _refine_ls_wR_factor_ref 0.1261 _refine_ls_wR_factor_gt 0.1158 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _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 N11 N 0.37691(9) 0.11595(6) 0.56216(5) 0.01596(16) Uani 1 1 d . . . N12 N 0.41024(10) 0.10909(7) 0.64582(5) 0.01992(18) Uani 1 1 d . . . N13 N 0.28686(10) 0.09315(7) 0.68532(5) 0.02019(18) Uani 1 1 d . . . N14 N 0.17212(9) 0.08893(7) 0.62921(5) 0.01662(17) Uani 1 1 d . . . C15 C 0.22262(10) 0.10358(7) 0.54918(6) 0.01525(18) Uani 1 1 d . . . O15 O 0.14916(8) 0.10444(6) 0.48463(4) 0.01996(16) Uani 1 1 d . . . C16 C 0.01749(11) 0.06842(9) 0.65424(6) 0.0222(2) Uani 1 1 d . . . H16A H -0.0371 0.1329 0.6610 0.033 Uiso 1 1 calc R . . H16B H 0.0174 0.0313 0.7074 0.033 Uiso 1 1 calc R . . H16C H -0.0325 0.0272 0.6113 0.033 Uiso 1 1 calc R . . C21 C 0.49455(10) 0.13013(7) 0.50264(6) 0.01508(17) Uani 1 1 d . . . C22 C 0.45627(10) 0.14563(8) 0.41952(6) 0.01780(19) Uani 1 1 d . . . H22 H 0.3531 0.1484 0.4030 0.021 Uiso 1 1 calc R . . C23 C 0.57120(11) 0.15704(8) 0.36061(6) 0.01706(19) Uani 1 1 d . . . O23 O 0.52277(8) 0.17061(7) 0.28019(4) 0.02428(19) Uani 1 1 d . . . C24 C 0.72252(11) 0.15421(8) 0.38482(6) 0.01807(19) Uani 1 1 d . . . H24 H 0.8008 0.1623 0.3447 0.022 Uiso 1 1 calc R . . C25 C 0.75733(11) 0.13933(8) 0.46892(6) 0.0194(2) Uani 1 1 d . . . H25 H 0.8605 0.1377 0.4857 0.023 Uiso 1 1 calc R . . C26 C 0.64516(11) 0.12691(8) 0.52867(6) 0.01813(19) Uani 1 1 d . . . H26 H 0.6702 0.1165 0.5858 0.022 Uiso 1 1 calc R . . C27 C 0.63719(12) 0.17761(9) 0.21718(6) 0.0242(2) Uani 1 1 d . . . H27A H 0.5893 0.1835 0.1622 0.036 Uiso 1 1 calc R . . H27B H 0.7005 0.1164 0.2187 0.036 Uiso 1 1 calc R . . H27C H 0.7001 0.2377 0.2275 0.036 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 N11 0.0138(3) 0.0213(4) 0.0128(3) -0.0003(3) -0.0010(3) 0.0002(3) N12 0.0184(4) 0.0288(4) 0.0126(3) -0.0012(3) -0.0013(3) 0.0003(3) N13 0.0190(4) 0.0267(4) 0.0149(3) -0.0009(3) -0.0021(3) 0.0000(3) N14 0.0155(3) 0.0217(4) 0.0127(3) -0.0006(3) 0.0008(3) -0.0006(3) C15 0.0143(4) 0.0173(4) 0.0142(4) -0.0009(3) 0.0009(3) -0.0001(3) O15 0.0154(3) 0.0290(4) 0.0154(3) 0.0013(3) -0.0019(2) -0.0016(3) C16 0.0175(4) 0.0298(5) 0.0194(4) -0.0002(4) 0.0042(3) -0.0033(4) C21 0.0126(4) 0.0170(4) 0.0156(4) -0.0009(3) 0.0003(3) 0.0002(3) C22 0.0132(4) 0.0250(5) 0.0153(4) -0.0004(3) 0.0002(3) 0.0002(3) C23 0.0143(4) 0.0217(4) 0.0151(4) -0.0012(3) 0.0013(3) 0.0001(3) O23 0.0159(3) 0.0431(5) 0.0139(3) 0.0026(3) 0.0024(2) -0.0009(3) C24 0.0125(4) 0.0195(4) 0.0222(4) -0.0014(3) 0.0022(3) -0.0004(3) C25 0.0131(4) 0.0219(5) 0.0232(4) -0.0008(4) -0.0012(3) -0.0004(3) C26 0.0143(4) 0.0208(4) 0.0193(4) -0.0001(3) -0.0020(3) 0.0002(3) C27 0.0207(4) 0.0340(6) 0.0178(4) -0.0010(4) 0.0063(4) -0.0042(4) _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 N11 N12 1.3737(11) . ? N11 C15 1.3881(12) . ? N11 C21 1.4219(12) . ? N12 N13 1.2770(12) . ? N13 N14 1.3552(11) . ? N14 C15 1.3697(11) . ? N14 C16 1.4486(13) . ? C15 O15 1.2199(11) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C21 C22 1.3874(13) . ? C21 C26 1.3947(13) . ? C22 C23 1.3936(13) . ? C22 H22 0.9500 . ? C23 O23 1.3678(11) . ? C23 C24 1.3921(13) . ? O23 C27 1.4306(12) . ? C24 C25 1.3942(14) . ? C24 H24 0.9500 . ? C25 C26 1.3865(14) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N12 N11 C15 110.40(8) . . ? N12 N11 C21 120.32(8) . . ? C15 N11 C21 129.24(8) . . ? N13 N12 N11 108.07(8) . . ? N12 N13 N14 108.48(8) . . ? N13 N14 C15 111.73(8) . . ? N13 N14 C16 121.97(8) . . ? C15 N14 C16 126.28(8) . . ? O15 C15 N14 128.31(9) . . ? O15 C15 N11 130.38(9) . . ? N14 C15 N11 101.32(7) . . ? N14 C16 H16A 109.5 . . ? N14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C22 C21 C26 121.55(9) . . ? C22 C21 N11 118.90(8) . . ? C26 C21 N11 119.54(8) . . ? C21 C22 C23 119.13(8) . . ? C21 C22 H22 120.4 . . ? C23 C22 H22 120.4 . . ? O23 C23 C24 124.45(8) . . ? O23 C23 C22 115.00(8) . . ? C24 C23 C22 120.55(9) . . ? C23 O23 C27 116.78(8) . . ? C23 C24 C25 118.96(9) . . ? C23 C24 H24 120.5 . . ? C25 C24 H24 120.5 . . ? C26 C25 C24 121.64(9) . . ? C26 C25 H25 119.2 . . ? C24 C25 H25 119.2 . . ? C25 C26 C21 118.17(9) . . ? C25 C26 H26 120.9 . . ? C21 C26 H26 120.9 . . ? O23 C27 H27A 109.5 . . ? O23 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? O23 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C15 N11 N12 N13 0.11(11) . . . . ? C21 N11 N12 N13 -177.82(8) . . . . ? N11 N12 N13 N14 0.22(11) . . . . ? N12 N13 N14 C15 -0.48(11) . . . . ? N12 N13 N14 C16 177.99(9) . . . . ? N13 N14 C15 O15 -179.95(10) . . . . ? C16 N14 C15 O15 1.65(17) . . . . ? N13 N14 C15 N11 0.51(10) . . . . ? C16 N14 C15 N11 -177.88(9) . . . . ? N12 N11 C15 O15 -179.90(10) . . . . ? C21 N11 C15 O15 -2.20(17) . . . . ? N12 N11 C15 N14 -0.37(10) . . . . ? C21 N11 C15 N14 177.32(9) . . . . ? N12 N11 C21 C22 -174.45(9) . . . . ? C15 N11 C21 C22 8.05(15) . . . . ? N12 N11 C21 C26 6.37(14) . . . . ? C15 N11 C21 C26 -171.13(10) . . . . ? C26 C21 C22 C23 0.75(15) . . . . ? N11 C21 C22 C23 -178.41(9) . . . . ? C21 C22 C23 O23 179.17(9) . . . . ? C21 C22 C23 C24 -0.79(15) . . . . ? C24 C23 O23 C27 2.95(15) . . . . ? C22 C23 O23 C27 -177.01(9) . . . . ? O23 C23 C24 C25 -179.67(10) . . . . ? C22 C23 C24 C25 0.28(15) . . . . ? C23 C24 C25 C26 0.28(15) . . . . ? C24 C25 C26 C21 -0.31(15) . . . . ? C22 C21 C26 C25 -0.21(15) . . . . ? N11 C21 C26 C25 178.95(9) . . . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 33.06 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.509 _refine_diff_density_min -0.231 _refine_diff_density_rms 0.055 #===END data_oa0801m _database_code_depnum_ccdc_archive 'CCDC 714343' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-(4-methoxyphenyl)-4-methyl-1,5-dihydro-5H-tetrazolone ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H10 N4 O2' _chemical_formula_sum 'C9 H10 N4 O2' _chemical_formula_weight 206.21 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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 3.8317(3) _cell_length_b 13.8861(13) _cell_length_c 17.7714(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 945.57(14) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3490 _cell_measurement_theta_min 2.72 _cell_measurement_theta_max 32.63 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.449 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 0.107 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7843 _diffrn_reflns_av_R_equivalents 0.0295 _diffrn_reflns_av_sigmaI/netI 0.0267 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 32.56 _reflns_number_total 2031 _reflns_number_gt 1830 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0750P)^2^+0.0400P] 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 2031 _refine_ls_number_parameters 138 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0429 _refine_ls_R_factor_gt 0.0378 _refine_ls_wR_factor_ref 0.1078 _refine_ls_wR_factor_gt 0.1030 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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 N11 N 0.4515(3) 0.51022(8) 0.49670(5) 0.0188(2) Uani 1 1 d . . . N12 N 0.3553(4) 0.53620(9) 0.56787(6) 0.0252(3) Uani 1 1 d . . . N13 N 0.4437(4) 0.46835(9) 0.61256(6) 0.0267(3) Uani 1 1 d . . . N14 N 0.5974(3) 0.39757(8) 0.57173(6) 0.0207(2) Uani 1 1 d . . . C15 C 0.6113(4) 0.42094(10) 0.49677(7) 0.0190(2) Uani 1 1 d . . . O15 O 0.7347(3) 0.37537(7) 0.44478(5) 0.0266(2) Uani 1 1 d . . . C16 C 0.7378(5) 0.31118(11) 0.60642(8) 0.0272(3) Uani 1 1 d . . . H16A H 0.8924 0.2784 0.5707 0.041 Uiso 1 1 calc R . . H16B H 0.5458 0.2681 0.6203 0.041 Uiso 1 1 calc R . . H16C H 0.8700 0.3288 0.6516 0.041 Uiso 1 1 calc R . . C21 C 0.4094(3) 0.57385(9) 0.43480(6) 0.0171(2) Uani 1 1 d . . . C22 C 0.5237(4) 0.66786(9) 0.44163(7) 0.0189(2) Uani 1 1 d . . . H22 H 0.6296 0.6888 0.4871 0.023 Uiso 1 1 calc R . . C23 C 0.4838(4) 0.73183(10) 0.38194(7) 0.0190(2) Uani 1 1 d . . . H23 H 0.5591 0.7968 0.3865 0.023 Uiso 1 1 calc R . . C24 C 0.3319(4) 0.69930(9) 0.31557(6) 0.0186(2) Uani 1 1 d . . . O24 O 0.2758(3) 0.75562(7) 0.25375(5) 0.0242(2) Uani 1 1 d . . . C25 C 0.2224(4) 0.60349(10) 0.30865(7) 0.0202(2) Uani 1 1 d . . . H25 H 0.1236 0.5816 0.2627 0.024 Uiso 1 1 calc R . . C26 C 0.2578(4) 0.54083(9) 0.36854(6) 0.0191(2) Uani 1 1 d . . . H26 H 0.1796 0.4761 0.3645 0.023 Uiso 1 1 calc R . . C27 C 0.4063(5) 0.85185(11) 0.25550(9) 0.0275(3) Uani 1 1 d . . . H27A H 0.3597 0.8832 0.2071 0.041 Uiso 1 1 calc R . . H27B H 0.6584 0.8507 0.2647 0.041 Uiso 1 1 calc R . . H27C H 0.2903 0.8877 0.2959 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 N11 0.0241(5) 0.0169(4) 0.0155(4) -0.0014(4) 0.0007(4) 0.0013(4) N12 0.0359(7) 0.0224(5) 0.0172(4) -0.0014(4) 0.0041(5) 0.0042(5) N13 0.0371(7) 0.0235(6) 0.0195(4) -0.0002(4) 0.0016(5) 0.0028(6) N14 0.0248(5) 0.0173(5) 0.0200(4) 0.0013(4) -0.0004(4) 0.0000(5) C15 0.0197(5) 0.0169(5) 0.0204(5) -0.0002(4) 0.0004(4) -0.0013(5) O15 0.0337(6) 0.0198(5) 0.0262(4) -0.0020(4) 0.0073(5) 0.0051(5) C16 0.0278(7) 0.0226(6) 0.0312(6) 0.0093(5) -0.0017(6) 0.0017(6) C21 0.0179(5) 0.0171(5) 0.0162(4) -0.0003(4) 0.0007(4) 0.0004(5) C22 0.0199(6) 0.0189(5) 0.0180(4) -0.0027(4) -0.0016(5) -0.0008(5) C23 0.0198(6) 0.0167(5) 0.0205(5) -0.0017(4) 0.0007(5) -0.0008(5) C24 0.0182(5) 0.0207(5) 0.0170(4) 0.0005(4) 0.0011(4) 0.0019(5) O24 0.0296(5) 0.0235(5) 0.0196(4) 0.0038(3) 0.0003(4) 0.0002(4) C25 0.0212(6) 0.0226(6) 0.0170(4) -0.0029(4) -0.0005(5) -0.0002(5) C26 0.0206(6) 0.0175(5) 0.0192(5) -0.0032(4) -0.0003(5) -0.0012(5) C27 0.0270(7) 0.0246(6) 0.0309(6) 0.0085(5) 0.0009(6) -0.0011(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 N11 N12 1.3660(14) . ? N11 C15 1.3826(17) . ? N11 C21 1.4201(15) . ? N12 N13 1.2779(17) . ? N13 N14 1.3562(17) . ? N14 C15 1.3721(16) . ? N14 C16 1.4520(18) . ? C15 O15 1.2157(15) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C21 C22 1.3824(18) . ? C21 C26 1.3909(16) . ? C22 C23 1.3920(18) . ? C22 H22 0.9500 . ? C23 C24 1.3906(17) . ? C23 H23 0.9500 . ? C24 O24 1.3657(15) . ? C24 C25 1.4004(19) . ? O24 C27 1.4270(18) . ? C25 C26 1.3813(18) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N12 N11 C15 110.82(10) . . ? N12 N11 C21 121.49(11) . . ? C15 N11 C21 127.51(10) . . ? N13 N12 N11 108.01(11) . . ? N12 N13 N14 108.48(10) . . ? N13 N14 C15 111.40(11) . . ? N13 N14 C16 122.17(11) . . ? C15 N14 C16 126.39(12) . . ? O15 C15 N14 129.04(13) . . ? O15 C15 N11 129.67(11) . . ? N14 C15 N11 101.29(10) . . ? N14 C16 H16A 109.5 . . ? N14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C22 C21 C26 121.20(11) . . ? C22 C21 N11 118.92(11) . . ? C26 C21 N11 119.88(12) . . ? C21 C22 C23 120.06(11) . . ? C21 C22 H22 120.0 . . ? C23 C22 H22 120.0 . . ? C24 C23 C22 119.01(12) . . ? C24 C23 H23 120.5 . . ? C22 C23 H23 120.5 . . ? O24 C24 C23 124.21(12) . . ? O24 C24 C25 115.23(11) . . ? C23 C24 C25 120.56(11) . . ? C24 O24 C27 117.62(11) . . ? C26 C25 C24 120.09(11) . . ? C26 C25 H25 120.0 . . ? C24 C25 H25 120.0 . . ? C25 C26 C21 119.06(12) . . ? C25 C26 H26 120.5 . . ? C21 C26 H26 120.5 . . ? O24 C27 H27A 109.5 . . ? O24 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? O24 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C15 N11 N12 N13 -0.31(17) . . . . ? C21 N11 N12 N13 -175.68(13) . . . . ? N11 N12 N13 N14 -0.03(18) . . . . ? N12 N13 N14 C15 0.36(18) . . . . ? N12 N13 N14 C16 178.05(14) . . . . ? N13 N14 C15 O15 178.82(15) . . . . ? C16 N14 C15 O15 1.2(3) . . . . ? N13 N14 C15 N11 -0.51(15) . . . . ? C16 N14 C15 N11 -178.09(14) . . . . ? N12 N11 C15 O15 -178.83(15) . . . . ? C21 N11 C15 O15 -3.8(2) . . . . ? N12 N11 C15 N14 0.49(15) . . . . ? C21 N11 C15 N14 175.52(13) . . . . ? N12 N11 C21 C22 48.16(19) . . . . ? C15 N11 C21 C22 -126.39(14) . . . . ? N12 N11 C21 C26 -132.36(14) . . . . ? C15 N11 C21 C26 53.1(2) . . . . ? C26 C21 C22 C23 0.9(2) . . . . ? N11 C21 C22 C23 -179.64(12) . . . . ? C21 C22 C23 C24 -0.8(2) . . . . ? C22 C23 C24 O24 179.22(13) . . . . ? C22 C23 C24 C25 -0.3(2) . . . . ? C23 C24 O24 C27 5.1(2) . . . . ? C25 C24 O24 C27 -175.31(13) . . . . ? O24 C24 C25 C26 -178.21(13) . . . . ? C23 C24 C25 C26 1.4(2) . . . . ? C24 C25 C26 C21 -1.3(2) . . . . ? C22 C21 C26 C25 0.2(2) . . . . ? N11 C21 C26 C25 -179.32(12) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 32.56 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.397 _refine_diff_density_min -0.218 _refine_diff_density_rms 0.051