Supplementary Material (ESI) for Chemical Communications This journal is (C) The Royal Society of Chemistry 2001 data_bmb1 _database_code_CSD 162685 _journal_coden_Cambridge 182 _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'Abell, Andrew D.' 'May, Barnaby C. H.' _publ_contact_author_name 'Dr Barnaby C H May' _publ_contact_author_address ; Dept of Cellular & Molecular Pharmacology University of California San Francisco San Francisco California 94143-0450 UNITED ARAB EMIRATES ; _publ_contact_author_email 'ALCHEMI@ITSA.UCSF.EDU' _publ_section_title ; The synthesis and solid state structure of (8S)-8-benzyl-8,9-dihydro-7H-tetrazolo[1,5-d][1,4] diazepin-6-one ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H13 N5 O' _chemical_formula_weight 243.27 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 6.374(2) _cell_length_b 8.621(3) _cell_length_c 20.890(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1147.8(7) _cell_formula_units_Z 4 _cell_measurement_temperature 163(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.63 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.408 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9418 _exptl_absorpt_correction_T_max 0.9800 _exptl_absorpt_process_details 'blessing Acta Cryst. (1995) A51 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 163(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14344 _diffrn_reflns_av_R_equivalents 0.0271 _diffrn_reflns_av_sigmaI/netI 0.0180 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.56 _diffrn_reflns_theta_max 26.42 _reflns_number_total 2338 _reflns_number_gt 2122 _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^)+(0.0595P)^2^+0.0493P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.3(14) _refine_ls_number_reflns 2338 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0374 _refine_ls_R_factor_gt 0.0323 _refine_ls_wR_factor_ref 0.0853 _refine_ls_wR_factor_gt 0.0827 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _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 N1 N 0.45573(18) 0.21516(14) 0.92461(6) 0.0279(3) Uani 1 1 d . . . H1 H 0.4193 0.3186 0.9228 0.033 Uiso 1 1 d R . . C2 C 0.4894(2) 0.14888(16) 0.98230(7) 0.0261(3) Uani 1 1 d . . . C3 C 0.5593(2) -0.02076(16) 0.98103(7) 0.0265(3) Uani 1 1 d . . . H3A H 0.5794 -0.0577 1.0255 0.032 Uiso 1 1 calc R . . H3B H 0.4477 -0.0845 0.9612 0.032 Uiso 1 1 calc R . . N2 N 0.75461(16) -0.04169(13) 0.94527(6) 0.0225(3) Uani 1 1 d . . . C5 C 0.8158(2) 0.00762(15) 0.88708(6) 0.0226(3) Uani 1 1 d . . . C6 C 0.6960(2) 0.10937(17) 0.84221(7) 0.0260(3) Uani 1 1 d . . . H6A H 0.6968 0.0609 0.7993 0.031 Uiso 1 1 calc R . . H6B H 0.7697 0.2101 0.8388 0.031 Uiso 1 1 calc R . . C7 C 0.4695(2) 0.13982(16) 0.86156(6) 0.0240(3) Uani 1 1 d . . . H7A H 0.3923 0.0389 0.8631 0.029 Uiso 1 1 calc R . . O1 O 0.46297(19) 0.21546(13) 1.03347(5) 0.0390(3) Uani 1 1 d . . . N3 N 0.91248(19) -0.12381(15) 0.97229(6) 0.0309(3) Uani 1 1 d . . . N4 N 1.06293(18) -0.12397(16) 0.93037(6) 0.0347(3) Uani 1 1 d . . . N5 N 1.00802(19) -0.04343(15) 0.87667(6) 0.0305(3) Uani 1 1 d . . . C8 C 0.3594(2) 0.24846(18) 0.81318(7) 0.0317(4) Uani 1 1 d . . . H8A H 0.2135 0.2659 0.8277 0.038 Uiso 1 1 calc R . . H8B H 0.4319 0.3500 0.8136 0.038 Uiso 1 1 calc R . . C9 C 0.3535(2) 0.18950(16) 0.74488(7) 0.0272(3) Uani 1 1 d . . . C10 C 0.5123(2) 0.22467(17) 0.70121(7) 0.0309(3) Uani 1 1 d . . . H10A H 0.6288 0.2850 0.7148 0.037 Uiso 1 1 calc R . . C11 C 0.5033(2) 0.17309(18) 0.63810(7) 0.0322(3) Uani 1 1 d . . . H11A H 0.6143 0.1970 0.6094 0.039 Uiso 1 1 calc R . . C12 C 0.3331(3) 0.08692(17) 0.61687(7) 0.0333(4) Uani 1 1 d . . . H12A H 0.3254 0.0532 0.5736 0.040 Uiso 1 1 calc R . . C13 C 0.1747(3) 0.0508(2) 0.65976(7) 0.0348(4) Uani 1 1 d . . . H13A H 0.0577 -0.0084 0.6458 0.042 Uiso 1 1 calc R . . C14 C 0.1851(2) 0.10032(19) 0.72279(7) 0.0327(3) Uani 1 1 d . . . H14A H 0.0757 0.0731 0.7516 0.039 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0286(6) 0.0260(6) 0.0290(6) -0.0034(5) -0.0002(5) 0.0064(5) C2 0.0174(6) 0.0327(7) 0.0283(8) -0.0040(6) 0.0025(5) 0.0004(6) C3 0.0223(7) 0.0307(7) 0.0265(7) 0.0008(6) 0.0047(6) -0.0003(6) N2 0.0175(5) 0.0241(6) 0.0257(6) 0.0001(5) -0.0015(4) 0.0001(5) C5 0.0186(6) 0.0245(7) 0.0248(7) -0.0024(5) -0.0003(5) -0.0028(5) C6 0.0214(7) 0.0308(7) 0.0257(7) 0.0033(6) 0.0010(5) 0.0025(6) C7 0.0209(7) 0.0264(7) 0.0247(7) -0.0013(6) -0.0001(5) 0.0019(5) O1 0.0441(7) 0.0432(6) 0.0298(6) -0.0080(5) 0.0042(5) 0.0066(5) N3 0.0232(6) 0.0350(7) 0.0345(7) 0.0047(6) -0.0046(5) 0.0041(5) N4 0.0218(6) 0.0426(7) 0.0397(7) 0.0044(6) -0.0012(6) 0.0043(6) N5 0.0197(6) 0.0371(6) 0.0348(7) 0.0013(6) 0.0010(5) 0.0028(5) C8 0.0307(8) 0.0319(8) 0.0325(8) -0.0006(6) -0.0049(6) 0.0093(6) C9 0.0249(7) 0.0269(8) 0.0298(8) 0.0039(6) -0.0043(6) 0.0065(6) C10 0.0285(8) 0.0290(7) 0.0352(8) 0.0072(6) -0.0047(6) -0.0006(6) C11 0.0305(7) 0.0341(8) 0.0320(8) 0.0100(6) 0.0034(6) 0.0021(6) C12 0.0388(8) 0.0344(8) 0.0269(8) 0.0019(6) -0.0034(6) 0.0054(7) C13 0.0283(7) 0.0394(8) 0.0366(8) 0.0014(8) -0.0073(6) -0.0032(7) C14 0.0232(7) 0.0412(9) 0.0337(8) 0.0053(7) 0.0003(6) 0.0004(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 N1 C2 1.3508(19) . ? N1 C7 1.4712(18) . ? C2 O1 1.2250(18) . ? C2 C3 1.529(2) . ? C3 N2 1.4632(17) . ? N2 C5 1.3455(18) . ? N2 N3 1.3537(16) . ? C5 N5 1.3201(19) . ? C5 C6 1.4934(19) . ? C6 C7 1.5221(19) . ? C7 C8 1.5463(19) . ? N3 N4 1.2987(18) . ? N4 N5 1.3650(18) . ? C8 C9 1.515(2) . ? C9 C10 1.396(2) . ? C9 C14 1.399(2) . ? C10 C11 1.393(2) . ? C11 C12 1.387(2) . ? C12 C13 1.385(2) . ? C13 C14 1.386(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 C2 N1 C7 127.05(12) . . ? O1 C2 N1 123.95(13) . . ? O1 C2 C3 120.21(14) . . ? N1 C2 C3 115.81(12) . . ? N2 C3 C2 112.01(11) . . ? C5 N2 N3 109.07(11) . . ? C5 N2 C3 131.98(12) . . ? N3 N2 C3 118.95(12) . . ? N5 C5 N2 108.21(12) . . ? N5 C5 C6 124.53(13) . . ? N2 C5 C6 127.19(13) . . ? C5 C6 C7 114.81(12) . . ? N1 C7 C6 111.74(11) . . ? N1 C7 C8 106.91(11) . . ? C6 C7 C8 111.19(12) . . ? N4 N3 N2 105.56(12) . . ? N3 N4 N5 111.37(11) . . ? C5 N5 N4 105.79(12) . . ? C9 C8 C7 115.05(12) . . ? C10 C9 C14 117.40(14) . . ? C10 C9 C8 121.66(14) . . ? C14 C9 C8 120.93(14) . . ? C11 C10 C9 121.29(15) . . ? C12 C11 C10 120.40(14) . . ? C13 C12 C11 118.90(14) . . ? C12 C13 C14 120.70(15) . . ? C13 C14 C9 121.29(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 C7 N1 C2 O1 -175.34(13) . . . . ? C7 N1 C2 C3 3.11(19) . . . . ? O1 C2 C3 N2 -122.61(14) . . . . ? N1 C2 C3 N2 58.87(16) . . . . ? C2 C3 N2 C5 -48.92(19) . . . . ? C2 C3 N2 N3 130.62(13) . . . . ? N3 N2 C5 N5 0.74(15) . . . . ? C3 N2 C5 N5 -179.68(13) . . . . ? N3 N2 C5 C6 -176.28(13) . . . . ? C3 N2 C5 C6 3.3(2) . . . . ? N5 C5 C6 C7 174.19(13) . . . . ? N2 C5 C6 C7 -9.2(2) . . . . ? C2 N1 C7 C6 -73.55(17) . . . . ? C2 N1 C7 C8 164.59(13) . . . . ? C5 C6 C7 N1 59.53(16) . . . . ? C5 C6 C7 C8 178.90(12) . . . . ? C5 N2 N3 N4 -0.62(15) . . . . ? C3 N2 N3 N4 179.74(12) . . . . ? N2 N3 N4 N5 0.27(16) . . . . ? N2 C5 N5 N4 -0.55(15) . . . . ? C6 C5 N5 N4 176.57(13) . . . . ? N3 N4 N5 C5 0.17(16) . . . . ? N1 C7 C8 C9 -179.00(12) . . . . ? C6 C7 C8 C9 58.80(16) . . . . ? C7 C8 C9 C10 -90.55(17) . . . . ? C7 C8 C9 C14 90.99(16) . . . . ? C14 C9 C10 C11 0.1(2) . . . . ? C8 C9 C10 C11 -178.45(13) . . . . ? C9 C10 C11 C12 1.0(2) . . . . ? C10 C11 C12 C13 -1.1(2) . . . . ? C11 C12 C13 C14 0.2(2) . . . . ? C12 C13 C14 C9 0.8(2) . . . . ? C10 C9 C14 C13 -1.0(2) . . . . ? C8 C9 C14 C13 177.54(14) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 26.42 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.148 _refine_diff_density_min -0.191 _refine_diff_density_rms 0.039