Supplementary Material (ESI) for Perkin Transactions This journal is © The Royal Society of Chemistry 2001 data_global _journal_coden_Cambridge 188 _publ_requested_journal 'Perkin Transactions 2' loop_ _publ_author_name 'Blake, Alexander J.' 'Blockhuys, Frank' 'Despinoy, Xavier L. M.' 'Harris, Steven G.' 'Hinchley, Sarah L.' 'McNab, H.' 'Rankin, D.' 'Robertson, Heather E.' _publ_contact_author_name 'Prof D Rankin' _publ_contact_author_address ; Prof D Rankin Department of Chemistry University of Edinburgh West Mains Road Edinburgh EH9 3JJ UK ; _publ_contact_author_email 'D.W.H.RANKIN@ED.AC.UK' _publ_section_title ; Pyrrolizin-3-One and Its 1,2-Dihydro Derivative: Structures of the Free Molecules Determined by Electron Diffraction and AB Initio Calculations and in the Crystal by X-ray Difraction ; data_PYRRLZ _database_code_CSD 161065 _audit_creation_method SHELXL _chemical_name_systematic ; PYRROLIZIN-3-ONE ; _chemical_name_common ? _chemical_formula_moiety 'C7 H5 N O' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C7 H5 N O' _chemical_formula_weight 119.12 _chemical_melting_point ? _chemical_compound_source ? 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 13.960(5) _cell_length_b 5.954(2) _cell_length_c 14.181(5) _cell_angle_alpha 90.00 _cell_angle_beta 104.42(4) _cell_angle_gamma 90.00 _cell_volume 1141.6(7) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 40 _cell_measurement_theta_min 12.5 _cell_measurement_theta_max 14.5 _exptl_crystal_description 'column within capillary tube' _exptl_crystal_colour orange _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.386 _exptl_crystal_density_method ? _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoKa _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Stoe Stadi-4 four-circle' _diffrn_measurement_method omega/2theta _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% none _diffrn_reflns_number 1756 _diffrn_reflns_av_R_equivalents 0.020 _diffrn_reflns_av_sigmaI/netI 0.021 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 30.06 _reflns_number_total 1674 _reflns_number_observed 1342 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'STADI-4' _computing_cell_refinement 'STADI-4' _computing_data_reduction 'X-RED' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material 'SHELXL-93; PLATON (Spek, 2001)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 17 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[s^2^(Fo^2^)+( 0.108P)^2^+0.434P] 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_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^l^3^/sin(2q)]^-1/4^' _refine_ls_number_reflns 1657 _refine_ls_number_parameters 103 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0669 _refine_ls_R_factor_obs 0.0531 _refine_ls_wR_factor_all 0.1676 _refine_ls_wR_factor_obs 0.1408 _refine_ls_goodness_of_fit_all 1.037 _refine_ls_goodness_of_fit_obs 1.042 _refine_ls_restrained_S_all 1.106 _refine_ls_restrained_S_obs 1.042 _refine_ls_shift/esd_max 0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group C1 C 0.65887(10) 0.3908(2) 0.66303(9) 0.0246(3) Uani 1 d . . H1 H 0.6481(14) 0.5301(35) 0.6922(14) 0.035(5) Uiso 1 d . . C2 C 0.59289(9) 0.2298(2) 0.62556(9) 0.0252(3) Uani 1 d . . H2 H 0.5212(14) 0.2279(32) 0.6213(13) 0.031(4) Uiso 1 d . . C3 C 0.64402(9) 0.0439(2) 0.58755(9) 0.0221(3) Uani 1 d . . O3 O 0.61273(7) -0.1325(2) 0.55040(7) 0.0303(3) Uani 1 d . . N4 N 0.74323(7) 0.1149(2) 0.60665(7) 0.0207(3) Uani 1 d . . C5 C 0.83140(9) 0.0446(2) 0.58838(9) 0.0241(3) Uani 1 d . . H5 H 0.8337(14) -0.0962(30) 0.5549(14) 0.028(4) Uiso 1 d . . C6 C 0.89948(9) 0.2085(2) 0.62295(9) 0.0276(3) Uani 1 d . . H6 H 0.9680(14) 0.2073(35) 0.6157(13) 0.033(5) Uiso 1 d . . C7 C 0.85159(10) 0.3857(2) 0.66271(9) 0.0269(3) Uani 1 d . . H7 H 0.8786(13) 0.5266(34) 0.6922(13) 0.034(5) Uiso 1 d . . C7a C 0.75541(9) 0.3229(2) 0.65112(8) 0.0219(3) Uani 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 C1 0.0300(6) 0.0240(6) 0.0199(5) -0.0002(4) 0.0063(4) 0.0052(5) C2 0.0242(6) 0.0275(6) 0.0246(6) 0.0024(5) 0.0074(4) 0.0040(4) C3 0.0221(5) 0.0228(6) 0.0202(5) 0.0016(4) 0.0031(4) -0.0005(4) O3 0.0302(5) 0.0240(5) 0.0350(5) -0.0042(4) 0.0049(4) -0.0046(4) N4 0.0205(5) 0.0200(5) 0.0203(5) -0.0022(4) 0.0030(3) 0.0002(3) C5 0.0236(5) 0.0273(6) 0.0212(5) 0.0005(4) 0.0050(4) 0.0035(4) C6 0.0230(6) 0.0351(7) 0.0239(6) 0.0010(5) 0.0043(4) -0.0012(5) C7 0.0293(6) 0.0279(6) 0.0214(5) -0.0012(5) 0.0023(4) -0.0057(5) C7a 0.0262(6) 0.0205(5) 0.0174(5) -0.0009(4) 0.0025(4) -0.0006(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 C1 C2 1.344(2) . ? C1 C7a 1.457(2) . ? C1 H1 0.96(2) . ? C2 C3 1.489(2) . ? C2 H2 0.99(2) . ? C3 O3 1.207(2) . ? C3 N4 1.408(2) . ? N4 C7a 1.381(2) . ? N4 C5 1.384(2) . ? C5 C6 1.365(2) . ? C5 H5 0.97(2) . ? C6 C7 1.437(2) . ? C6 H6 0.99(2) . ? C7 C7a 1.364(2) . ? C7 H7 0.97(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 C1 C7a 108.58(11) . . ? C2 C1 H1 128.6(11) . . ? C7a C1 H1 122.8(11) . . ? C1 C2 C3 109.29(11) . . ? C1 C2 H2 128.0(11) . . ? C3 C2 H2 122.7(11) . . ? O3 C3 N4 125.22(12) . . ? O3 C3 C2 130.61(12) . . ? N4 C3 C2 104.14(11) . . ? C7a N4 C5 110.03(10) . . ? C7a N4 C3 111.13(10) . . ? C5 N4 C3 138.68(11) . . ? C6 C5 N4 106.79(11) . . ? C6 C5 H5 133.6(11) . . ? N4 C5 H5 119.5(11) . . ? C5 C6 C7 108.38(12) . . ? C5 C6 H6 124.3(12) . . ? C7 C6 H6 127.1(12) . . ? C7a C7 C6 106.95(12) . . ? C7a C7 H7 123.6(10) . . ? C6 C7 H7 129.4(10) . . ? C7 C7a N4 107.85(11) . . ? C7 C7a C1 145.23(13) . . ? N4 C7a C1 106.85(10) . . ? 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 C7a C1 C2 C3 0.62(14) . . . . ? C1 C2 C3 O3 178.29(13) . . . . ? C1 C2 C3 N4 -0.16(14) . . . . ? O3 C3 N4 C7a -178.96(12) . . . . ? C2 C3 N4 C7a -0.40(13) . . . . ? O3 C3 N4 C5 6.5(2) . . . . ? C2 C3 N4 C5 -174.90(13) . . . . ? C7a N4 C5 C6 0.85(14) . . . . ? C3 N4 C5 C6 175.39(14) . . . . ? N4 C5 C6 C7 -0.61(15) . . . . ? C5 C6 C7 C7a 0.2(2) . . . . ? C6 C7 C7a N4 0.36(14) . . . . ? C6 C7 C7a C1 -175.7(2) . . . . ? C5 N4 C7a C7 -0.76(14) . . . . ? C3 N4 C7a C7 -176.90(10) . . . . ? C5 N4 C7a C1 176.90(9) . . . . ? C3 N4 C7a C1 0.77(13) . . . . ? C2 C1 C7a C7 175.2(2) . . . . ? C2 C1 C7a N4 -0.86(14) . . . . ? _refine_diff_density_max 0.44 _refine_diff_density_min -0.34 _refine_diff_density_rms 0.07 data_DIHYPZ _database_code_CSD 168077 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C7 H7 N O' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C7 H7 N O' _chemical_formula_weight 121.14 _chemical_melting_point ? _chemical_compound_source ? 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)/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 6.629(5) _cell_length_b 12.996(9) _cell_length_c 7.373(5) _cell_angle_alpha 90.00 _cell_angle_beta 109.78(5) _cell_angle_gamma 90.00 _cell_volume 597.7(7) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 33 _cell_measurement_theta_min 14 _cell_measurement_theta_max 16 _exptl_crystal_description 'Hexagonal prism' _exptl_crystal_colour 'Pale yellow' _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.47 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.346 _exptl_crystal_density_method ? _exptl_crystal_F_000 256 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Stoe Stadi-4' _diffrn_measurement_method '\w-2\q scans' _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 3% _diffrn_reflns_number 2574 _diffrn_reflns_av_R_equivalents 0.024 _diffrn_reflns_av_sigmaI/netI 0.019 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.94 _diffrn_reflns_theta_max 25.01 _reflns_number_total 1052 _reflns_number_observed 914 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Stoe DIF4' _computing_cell_refinement 'Stoe DIF4' _computing_data_reduction 'Stoe REDU4' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'SHELXTL/PC (Sheldrick, 1992)' _computing_publication_material 'SHELXL-93; PLATON (Spek, 2001)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 4 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0512P)^2^+0.1435P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment 'refined x,y,z and U(iso)' _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.053(7) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1048 _refine_ls_number_parameters 111 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0415 _refine_ls_R_factor_obs 0.0340 _refine_ls_wR_factor_all 0.0937 _refine_ls_wR_factor_obs 0.0874 _refine_ls_goodness_of_fit_all 1.089 _refine_ls_goodness_of_fit_obs 1.123 _refine_ls_restrained_S_all 1.114 _refine_ls_restrained_S_obs 1.123 _refine_ls_shift/esd_max 0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group C1 C 0.7561(2) 0.92835(11) 0.4017(2) 0.0259(4) Uani 1 d . . H1A H 0.8598(26) 0.9019(12) 0.3441(23) 0.034(4) Uiso 1 d . . H1B H 0.8336(25) 0.9428(11) 0.5420(24) 0.027(4) Uiso 1 d . . C2 C 0.5680(2) 0.85243(10) 0.3707(2) 0.0247(4) Uani 1 d . . H2A H 0.5501(26) 0.8318(13) 0.4936(24) 0.034(4) Uiso 1 d . . H2B H 0.5843(26) 0.7904(13) 0.3055(22) 0.031(4) Uiso 1 d . . C3 C 0.3664(2) 0.90699(10) 0.2472(2) 0.0218(3) Uani 1 d . . O3 O 0.1828(2) 0.87559(7) 0.18696(15) 0.0313(3) Uani 1 d . . N4 N 0.4287(2) 1.00544(8) 0.21400(15) 0.0207(3) Uani 1 d . . C5 C 0.3263(2) 1.09117(10) 0.1117(2) 0.0248(4) Uani 1 d . . H5 H 0.1786(29) 1.0920(12) 0.0446(23) 0.030(4) Uiso 1 d . . C6 C 0.4829(2) 1.16275(10) 0.1327(2) 0.0269(4) Uani 1 d . . H6 H 0.4597(27) 1.2294(13) 0.0731(23) 0.035(4) Uiso 1 d . . C7 C 0.6855(2) 1.12049(10) 0.2497(2) 0.0267(4) Uani 1 d . . H7 H 0.8235(29) 1.1557(14) 0.2890(24) 0.038(4) Uiso 1 d . . C7A C 0.6475(2) 1.02320(10) 0.2971(2) 0.0214(3) Uani 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 C1 0.0247(7) 0.0260(7) 0.0286(8) 0.0015(6) 0.0111(6) 0.0042(6) C2 0.0312(8) 0.0183(7) 0.0266(7) 0.0006(5) 0.0123(6) 0.0024(5) C3 0.0267(8) 0.0185(6) 0.0230(7) -0.0032(5) 0.0122(6) -0.0016(5) O3 0.0272(6) 0.0286(6) 0.0373(6) -0.0005(4) 0.0098(4) -0.0071(4) N4 0.0218(6) 0.0179(6) 0.0228(6) -0.0007(4) 0.0080(5) 0.0008(4) C5 0.0287(8) 0.0219(7) 0.0234(7) 0.0009(5) 0.0082(6) 0.0060(6) C6 0.0403(9) 0.0179(7) 0.0254(7) 0.0006(6) 0.0149(6) 0.0018(6) C7 0.0311(8) 0.0226(7) 0.0296(7) -0.0027(6) 0.0144(6) -0.0052(6) C7A 0.0214(7) 0.0222(7) 0.0227(7) -0.0035(5) 0.0101(5) -0.0008(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 C1 C7A 1.502(2) . ? C1 C2 1.545(2) . ? C2 C3 1.515(2) . ? C3 O3 1.216(2) . ? C3 N4 1.392(2) . ? N4 C5 1.387(2) . ? N4 C7A 1.390(2) . ? C5 C6 1.363(2) . ? C6 C7 1.437(2) . ? C7 C7A 1.358(2) . ? C1 H1A 0.984(16) . ? C1 H1B 1.005(16) . ? C2 H2A 0.990(16) . ? C2 H2B 0.963(16) . ? C5 H5 0.936(18) . ? C6 H6 0.960(17) . ? C7 H7 0.975(18) . ? 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 C7A C1 C2 103.03(12) . . ? C3 C2 C1 107.09(12) . . ? O3 C3 N4 124.35(13) . . ? O3 C3 C2 129.26(13) . . ? N4 C3 C2 106.38(12) . . ? C5 N4 C7A 110.62(12) . . ? C5 N4 C3 135.58(13) . . ? C7A N4 C3 113.76(11) . . ? C6 C5 N4 105.80(14) . . ? C5 C6 C7 109.20(13) . . ? C7A C7 C6 107.04(13) . . ? C7 C7A N4 107.34(12) . . ? C7 C7A C1 142.92(13) . . ? N4 C7A C1 109.71(12) . . ? C7A C1 H1A 110.3(9) . . ? C2 C1 H1A 111.1(10) . . ? C7A C1 H1B 111.4(9) . . ? C2 C1 H1B 112.2(9) . . ? H1A C1 H1B 108.7(13) . . ? C3 C2 H2A 108.8(10) . . ? C1 C2 H2A 112.2(10) . . ? C3 C2 H2B 108.5(10) . . ? C1 C2 H2B 112.8(9) . . ? H2A C2 H2B 107.4(13) . . ? C6 C5 H5 132.3(10) . . ? N4 C5 H5 121.9(10) . . ? C5 C6 H6 124.4(10) . . ? C7 C6 H6 126.3(10) . . ? C7A C7 H7 126.7(11) . . ? C6 C7 H7 126.3(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 C7A C1 C2 C3 1.40(13) . . . . ? C1 C2 C3 O3 179.31(12) . . . . ? C1 C2 C3 N4 -1.49(14) . . . . ? O3 C3 N4 C5 -2.3(2) . . . . ? C2 C3 N4 C5 178.49(13) . . . . ? O3 C3 N4 C7A -179.74(12) . . . . ? C2 C3 N4 C7A 1.01(14) . . . . ? C7A N4 C5 C6 -0.39(14) . . . . ? C3 N4 C5 C6 -177.93(13) . . . . ? N4 C5 C6 C7 0.11(14) . . . . ? C5 C6 C7 C7A 0.20(15) . . . . ? C6 C7 C7A N4 -0.43(14) . . . . ? C6 C7 C7A C1 177.6(2) . . . . ? C5 N4 C7A C7 0.52(14) . . . . ? C3 N4 C7A C7 178.64(10) . . . . ? C5 N4 C7A C1 -178.20(10) . . . . ? C3 N4 C7A C1 -0.08(14) . . . . ? C2 C1 C7A C7 -178.8(2) . . . . ? C2 C1 C7A N4 -0.85(13) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.22 _refine_diff_density_min -0.22 _refine_diff_density_rms 0.04