# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Prof D Boyd' _publ_contact_author_email DR.BOYD@QUB.AC.UK _publ_section_title ; Regioselectivity and stereoselectivity of dioxygenase catalysed cis-dihydroxylation of mono- and tri-cyclic azaarene substrates ; loop_ _publ_author_name 'D. Boyd' 'Christopher C. R. Allen' 'Gerard P. Coen' 'T. G. Hamilton' 'Francis Hempenstall' ; V.Ljubez ; 'J. Malone' 'Narain D. Sharma' # Attachment '2e1.cif' data_2e _database_code_depnum_ccdc_archive 'CCDC 691141' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H11 N O2' _chemical_formula_sum 'C10 H11 N O2' _chemical_formula_weight 177.20 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 13.076(4) _cell_length_b 4.980(2) _cell_length_c 21.362(11) _cell_angle_alpha 90.00 _cell_angle_beta 103.18(3) _cell_angle_gamma 90.00 _cell_volume 1354.5(10) _cell_formula_units_Z 6 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.43 _exptl_crystal_size_min 0.41 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.303 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 564 _exptl_absorpt_coefficient_mu 0.747 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens P3 diffractometer' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 1 _diffrn_standards_interval_count 99 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 3971 _diffrn_reflns_av_R_equivalents 0.1113 _diffrn_reflns_av_sigmaI/netI 0.0433 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 55.05 _reflns_number_total 3307 _reflns_number_gt 3210 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens P3/V2000' _computing_cell_refinement 'Siemens P3/V2000' _computing_data_reduction 'Siemens P3/V2000' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1732P)^2^+0.3283P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.081(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _chemical_absolute_configuration ad _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.07(18) _refine_ls_number_reflns 3307 _refine_ls_number_parameters 358 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0752 _refine_ls_R_factor_gt 0.0741 _refine_ls_wR_factor_ref 0.2061 _refine_ls_wR_factor_gt 0.2037 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.002 _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 C1A C 0.3413(3) 0.9210(9) 0.9495(2) 0.0483(10) Uani 1 1 d . . . H1A H 0.3540 0.7702 0.9797 0.058 Uiso 1 1 calc R . . O1A O 0.4315(2) 0.9529(7) 0.92404(15) 0.0557(8) Uani 1 1 d . . . H1A1 H 0.4426 0.8136 0.9062 0.084 Uiso 1 1 calc R . . C2A C 0.2447(3) 0.8535(9) 0.8962(2) 0.0478(10) Uani 1 1 d . . . H2A H 0.2510 0.6695 0.8813 0.057 Uiso 1 1 calc R . . O2A O 0.2374(2) 1.0390(7) 0.84262(13) 0.0573(9) Uani 1 1 d . . . H2A1 H 0.2951 1.0533 0.8340 0.086 Uiso 1 1 calc R . . C3A C 0.1468(3) 0.8783(9) 0.9197(2) 0.0496(10) Uani 1 1 d . . . C4A C 0.1425(4) 1.0493(12) 0.9672(2) 0.0639(13) Uani 1 1 d . . . H4A H 0.0814 1.0610 0.9825 0.077 Uiso 1 1 calc R . . C5A C 0.2316(4) 1.2162(11) 0.9952(2) 0.0632(12) Uani 1 1 d . . . H5A H 0.2220 1.3620 1.0205 0.076 Uiso 1 1 calc R . . C6A C 0.3248(4) 1.1683(9) 0.9861(2) 0.0559(12) Uani 1 1 d . . . H6A H 0.3802 1.2849 1.0020 0.067 Uiso 1 1 calc R . . N7A N 0.0574(3) 0.7355(8) 0.88733(17) 0.0526(9) Uani 1 1 d . . . C8A C -0.0437(4) 0.7720(13) 0.8937(3) 0.0708(14) Uani 1 1 d . . . H8A H -0.0657 0.9065 0.9178 0.085 Uiso 1 1 calc R . . C9A C -0.1062(4) 0.5836(13) 0.8596(3) 0.0743(16) Uani 1 1 d . . . H9A H -0.1781 0.5649 0.8560 0.089 Uiso 1 1 calc R . . C10A C -0.0427(4) 0.4200(13) 0.8304(3) 0.0748(15) Uani 1 1 d . . . H10A H -0.0650 0.2733 0.8039 0.090 Uiso 1 1 calc R . . C11A C 0.0557(4) 0.5138(10) 0.8478(2) 0.0633(13) Uani 1 1 d . . . H11A H 0.1137 0.4418 0.8354 0.076 Uiso 1 1 calc R . . C1B C 0.1297(3) 1.3180(9) 0.6553(2) 0.0540(11) Uani 1 1 d . . . H1B H 0.0858 1.4646 0.6333 0.065 Uiso 1 1 calc R . . O1B O 0.2026(2) 1.4304(7) 0.70785(17) 0.0673(9) Uani 1 1 d . . . H1B1 H 0.1855 1.5853 0.7135 0.101 Uiso 1 1 calc R . . C2B C 0.0581(3) 1.1222(9) 0.6797(2) 0.0533(11) Uani 1 1 d . . . H2B H 0.0135 1.2222 0.7027 0.064 Uiso 1 1 calc R . . O2B O 0.1159(3) 0.9221(7) 0.72167(14) 0.0611(9) Uani 1 1 d . . . H2B1 H 0.1502 0.9944 0.7542 0.092 Uiso 1 1 calc R . . C3B C -0.0107(3) 0.9771(9) 0.6232(2) 0.0526(11) Uani 1 1 d . . . C4B C 0.0263(4) 0.9312(11) 0.5705(2) 0.0612(12) Uani 1 1 d . . . H4B H -0.0163 0.8437 0.5356 0.073 Uiso 1 1 calc R . . C5B C 0.1290(4) 1.0126(12) 0.5663(2) 0.0678(14) Uani 1 1 d . . . H5B H 0.1589 0.9413 0.5344 0.081 Uiso 1 1 calc R . . C6B C 0.1819(4) 1.1883(11) 0.6073(2) 0.0662(13) Uani 1 1 d . . . H6B H 0.2508 1.2314 0.6065 0.079 Uiso 1 1 calc R . . N7B N -0.1080(3) 0.8860(9) 0.63058(19) 0.0620(11) Uani 1 1 d . . . C8B C -0.1956(5) 0.8369(16) 0.5839(3) 0.0880(18) Uani 1 1 d . . . H8B H -0.2044 0.8773 0.5405 0.106 Uiso 1 1 calc R . . C9B C -0.2681(5) 0.7194(18) 0.6112(4) 0.108(2) Uani 1 1 d . . . H9B H -0.3338 0.6576 0.5897 0.129 Uiso 1 1 calc R . . C10B C -0.2273(5) 0.7077(16) 0.6764(3) 0.0924(19) Uani 1 1 d . . . H10B H -0.2615 0.6408 0.7068 0.111 Uiso 1 1 calc R . . C11B C -0.1299(5) 0.8093(13) 0.6887(3) 0.0750(15) Uani 1 1 d . . . H11B H -0.0848 0.8257 0.7290 0.090 Uiso 1 1 calc R . . C1C C 0.5383(3) 0.4310(9) 0.8388(2) 0.0558(11) Uani 1 1 d . . . H1C H 0.5787 0.5971 0.8394 0.067 Uiso 1 1 calc R . . O1C O 0.4831(3) 0.4593(7) 0.88910(16) 0.0672(9) Uani 1 1 d . . . H1C1 H 0.4620 0.3033 0.8900 0.100 Uiso 1 1 d . . . C2C C 0.4653(3) 0.4205(10) 0.7736(2) 0.0539(10) Uani 1 1 d . . . H2C H 0.4294 0.5937 0.7646 0.065 Uiso 1 1 calc R . . O2C O 0.3885(2) 0.2130(7) 0.77118(14) 0.0585(9) Uani 1 1 d . . . H2C1 H 0.3313 0.2659 0.7506 0.088 Uiso 1 1 calc R . . C3C C 0.5262(3) 0.3637(9) 0.7224(2) 0.0550(12) Uani 1 1 d . . . C4C C 0.6146(3) 0.2158(11) 0.7378(2) 0.0639(13) Uani 1 1 d . . . H4C H 0.6504 0.1739 0.7061 0.077 Uiso 1 1 calc R . . C5C C 0.6547(3) 0.1208(12) 0.8027(3) 0.0717(15) Uani 1 1 d . . . H5C H 0.7082 -0.0064 0.8105 0.086 Uiso 1 1 calc R . . C6C C 0.6172(3) 0.2108(12) 0.8510(2) 0.0664(13) Uani 1 1 d . . . H6C H 0.6396 0.1381 0.8920 0.080 Uiso 1 1 calc R . . N7C N 0.4803(3) 0.4402(8) 0.65875(18) 0.0594(10) Uani 1 1 d . . . C8C C 0.4950(4) 0.3133(13) 0.6038(3) 0.0743(15) Uani 1 1 d . . . H8C H 0.5340 0.1579 0.6027 0.089 Uiso 1 1 calc R . . C9C C 0.4436(5) 0.4523(15) 0.5526(3) 0.0864(18) Uani 1 1 d . . . H9C H 0.4403 0.4101 0.5098 0.104 Uiso 1 1 calc R . . C10C C 0.3960(5) 0.6711(13) 0.5749(3) 0.0802(16) Uani 1 1 d . . . H10C H 0.3554 0.8019 0.5498 0.096 Uiso 1 1 calc R . . C11C C 0.4196(4) 0.6589(12) 0.6394(3) 0.0719(14) Uani 1 1 d . . . H11C H 0.3977 0.7813 0.6665 0.086 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 C1A 0.041(2) 0.054(2) 0.047(2) 0.0050(19) 0.0018(16) 0.0017(18) O1A 0.0431(15) 0.0589(17) 0.0625(18) 0.0012(15) 0.0067(12) 0.0011(14) C2A 0.046(2) 0.049(2) 0.047(2) 0.0040(18) 0.0059(18) -0.0001(18) O2A 0.0415(14) 0.092(2) 0.0371(16) 0.0071(14) 0.0062(12) 0.0013(15) C3A 0.047(2) 0.051(2) 0.048(2) 0.0023(18) 0.0061(18) -0.0029(18) C4A 0.057(3) 0.083(3) 0.055(3) -0.011(2) 0.020(2) -0.009(2) C5A 0.064(3) 0.082(3) 0.044(2) -0.010(2) 0.013(2) -0.006(3) C6A 0.057(3) 0.064(3) 0.041(2) -0.001(2) -0.0013(19) -0.009(2) N7A 0.0457(19) 0.060(2) 0.0511(19) -0.0004(17) 0.0092(15) -0.0057(17) C8A 0.049(3) 0.082(3) 0.087(3) -0.007(3) 0.027(2) -0.013(3) C9A 0.048(3) 0.095(4) 0.080(4) 0.006(3) 0.015(2) -0.017(3) C10A 0.063(3) 0.085(4) 0.071(3) -0.002(3) 0.003(3) -0.019(3) C11A 0.056(3) 0.069(3) 0.064(3) -0.009(2) 0.011(2) -0.005(2) C1B 0.047(2) 0.054(2) 0.054(2) 0.0081(19) -0.0044(19) -0.0014(19) O1B 0.0537(17) 0.0611(18) 0.076(2) -0.0059(17) -0.0083(15) -0.0014(15) C2B 0.049(2) 0.058(3) 0.050(2) -0.0026(19) 0.0048(19) 0.005(2) O2B 0.079(2) 0.0555(17) 0.0395(15) 0.0004(13) -0.0067(14) 0.0034(16) C3B 0.048(2) 0.060(3) 0.043(2) 0.006(2) -0.0029(17) 0.005(2) C4B 0.065(3) 0.074(3) 0.038(2) 0.001(2) -0.0027(19) -0.002(2) C5B 0.062(3) 0.096(4) 0.044(2) 0.004(3) 0.009(2) 0.005(3) C6B 0.054(3) 0.081(3) 0.061(3) 0.010(3) 0.008(2) -0.002(3) N7B 0.049(2) 0.078(3) 0.054(2) 0.002(2) 0.0043(16) -0.0090(19) C8B 0.071(3) 0.112(5) 0.071(3) -0.006(3) -0.005(3) -0.017(3) C9B 0.063(3) 0.137(7) 0.118(6) -0.002(5) 0.009(3) -0.039(4) C10B 0.076(4) 0.109(5) 0.094(4) -0.003(4) 0.024(3) -0.025(4) C11B 0.074(3) 0.086(4) 0.066(3) -0.006(3) 0.017(2) -0.015(3) C1C 0.055(2) 0.053(2) 0.062(3) -0.001(2) 0.016(2) -0.013(2) O1C 0.080(2) 0.0609(19) 0.064(2) -0.0099(16) 0.0229(16) -0.0086(17) C2C 0.048(2) 0.053(2) 0.063(3) -0.001(2) 0.0165(19) -0.002(2) O2C 0.0391(15) 0.077(2) 0.0596(18) 0.0082(16) 0.0109(13) -0.0055(15) C3C 0.050(2) 0.056(3) 0.062(3) -0.006(2) 0.019(2) -0.007(2) C4C 0.053(3) 0.073(3) 0.071(3) 0.001(3) 0.024(2) 0.001(2) C5C 0.042(2) 0.081(3) 0.092(4) 0.014(3) 0.017(3) 0.010(2) C6C 0.049(2) 0.083(3) 0.064(3) 0.007(3) 0.007(2) -0.011(2) N7C 0.060(2) 0.064(2) 0.057(2) 0.000(2) 0.0207(17) -0.002(2) C8C 0.074(3) 0.083(4) 0.066(3) -0.008(3) 0.017(3) -0.004(3) C9C 0.083(3) 0.113(5) 0.065(3) -0.008(3) 0.019(3) -0.028(4) C10C 0.079(3) 0.093(4) 0.064(3) 0.017(3) 0.006(3) -0.003(3) C11C 0.072(3) 0.078(3) 0.065(3) 0.011(3) 0.015(2) 0.002(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 C1A O1A 1.415(5) . ? C1A C6A 1.501(7) . ? C1A C2A 1.532(6) . ? C2A O2A 1.458(5) . ? C2A C3A 1.482(6) . ? C3A C4A 1.336(7) . ? C3A N7A 1.408(6) . ? C4A C5A 1.445(7) . ? C5A C6A 1.299(7) . ? N7A C8A 1.372(6) . ? N7A C11A 1.387(7) . ? C8A C9A 1.344(8) . ? C9A C10A 1.406(9) . ? C10A C11A 1.340(7) . ? C1B O1B 1.411(5) . ? C1B C6B 1.501(7) . ? C1B C2B 1.523(6) . ? C2B O2B 1.435(5) . ? C2B C3B 1.514(6) . ? C3B C4B 1.344(7) . ? C3B N7B 1.392(6) . ? C4B C5B 1.424(7) . ? C5B C6B 1.317(8) . ? N7B C8B 1.359(7) . ? N7B C11B 1.390(7) . ? C8B C9B 1.353(10) . ? C9B C10B 1.375(11) . ? C10B C11B 1.340(9) . ? C1C O1C 1.431(6) . ? C1C C6C 1.488(7) . ? C1C C2C 1.499(6) . ? C2C O2C 1.433(5) . ? C2C C3C 1.520(7) . ? C3C C4C 1.347(7) . ? C3C N7C 1.407(6) . ? C4C C5C 1.446(8) . ? C5C C6C 1.319(8) . ? N7C C11C 1.356(7) . ? N7C C8C 1.384(7) . ? C8C C9C 1.339(9) . ? C9C C10C 1.392(9) . ? C10C C11C 1.342(8) . ? 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 O1A C1A C6A 109.9(4) . . ? O1A C1A C2A 111.0(3) . . ? C6A C1A C2A 112.0(3) . . ? O2A C2A C3A 107.8(3) . . ? O2A C2A C1A 109.8(3) . . ? C3A C2A C1A 111.1(4) . . ? C4A C3A N7A 121.4(4) . . ? C4A C3A C2A 120.0(4) . . ? N7A C3A C2A 118.5(4) . . ? C3A C4A C5A 120.7(4) . . ? C6A C5A C4A 121.9(5) . . ? C5A C6A C1A 118.7(4) . . ? C8A N7A C11A 106.5(4) . . ? C8A N7A C3A 126.6(4) . . ? C11A N7A C3A 126.7(4) . . ? C9A C8A N7A 109.5(5) . . ? C8A C9A C10A 107.3(4) . . ? C11A C10A C9A 107.5(5) . . ? C10A C11A N7A 109.1(5) . . ? O1B C1B C6B 112.6(4) . . ? O1B C1B C2B 109.8(4) . . ? C6B C1B C2B 111.6(4) . . ? O2B C2B C3B 107.4(4) . . ? O2B C2B C1B 112.4(3) . . ? C3B C2B C1B 109.5(4) . . ? C4B C3B N7B 123.5(4) . . ? C4B C3B C2B 119.1(4) . . ? N7B C3B C2B 117.3(4) . . ? C3B C4B C5B 121.9(4) . . ? C6B C5B C4B 120.5(5) . . ? C5B C6B C1B 119.3(4) . . ? C8B N7B C11B 107.1(5) . . ? C8B N7B C3B 128.0(4) . . ? C11B N7B C3B 124.7(4) . . ? C9B C8B N7B 108.6(6) . . ? C8B C9B C10B 107.8(5) . . ? C11B C10B C9B 108.3(6) . . ? C10B C11B N7B 108.0(5) . . ? O1C C1C C6C 112.9(4) . . ? O1C C1C C2C 112.2(4) . . ? C6C C1C C2C 114.0(4) . . ? O2C C2C C1C 110.6(4) . . ? O2C C2C C3C 108.5(4) . . ? C1C C2C C3C 110.4(4) . . ? C4C C3C N7C 122.5(4) . . ? C4C C3C C2C 119.1(4) . . ? N7C C3C C2C 117.9(4) . . ? C3C C4C C5C 121.2(5) . . ? C6C C5C C4C 121.4(5) . . ? C5C C6C C1C 118.7(5) . . ? C11C N7C C8C 107.0(4) . . ? C11C N7C C3C 127.1(4) . . ? C8C N7C C3C 125.7(4) . . ? C9C C8C N7C 108.4(5) . . ? C8C C9C C10C 107.8(5) . . ? C11C C10C C9C 107.4(5) . . ? C10C C11C N7C 109.4(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 O1A C1A C2A O2A -48.4(5) . . . . ? C6A C1A C2A O2A 74.8(4) . . . . ? O1A C1A C2A C3A -167.6(4) . . . . ? C6A C1A C2A C3A -44.4(5) . . . . ? O2A C2A C3A C4A -92.4(5) . . . . ? C1A C2A C3A C4A 28.0(6) . . . . ? O2A C2A C3A N7A 82.5(5) . . . . ? C1A C2A C3A N7A -157.1(4) . . . . ? N7A C3A C4A C5A -173.1(4) . . . . ? C2A C3A C4A C5A 1.5(7) . . . . ? C3A C4A C5A C6A -15.3(8) . . . . ? C4A C5A C6A C1A -4.5(7) . . . . ? O1A C1A C6A C5A 158.2(4) . . . . ? C2A C1A C6A C5A 34.4(6) . . . . ? C4A C3A N7A C8A 8.2(7) . . . . ? C2A C3A N7A C8A -166.5(4) . . . . ? C4A C3A N7A C11A -164.9(5) . . . . ? C2A C3A N7A C11A 20.3(6) . . . . ? C11A N7A C8A C9A -0.3(6) . . . . ? C3A N7A C8A C9A -174.6(5) . . . . ? N7A C8A C9A C10A 0.1(6) . . . . ? C8A C9A C10A C11A 0.2(6) . . . . ? C9A C10A C11A N7A -0.3(6) . . . . ? C8A N7A C11A C10A 0.4(6) . . . . ? C3A N7A C11A C10A 174.6(4) . . . . ? O1B C1B C2B O2B -53.8(5) . . . . ? C6B C1B C2B O2B 71.8(5) . . . . ? O1B C1B C2B C3B -173.0(4) . . . . ? C6B C1B C2B C3B -47.5(5) . . . . ? O2B C2B C3B C4B -91.5(5) . . . . ? C1B C2B C3B C4B 30.8(6) . . . . ? O2B C2B C3B N7B 85.3(5) . . . . ? C1B C2B C3B N7B -152.4(4) . . . . ? N7B C3B C4B C5B -175.9(5) . . . . ? C2B C3B C4B C5B 0.7(7) . . . . ? C3B C4B C5B C6B -15.8(8) . . . . ? C4B C5B C6B C1B -4.7(7) . . . . ? O1B C1B C6B C5B 160.9(5) . . . . ? C2B C1B C6B C5B 36.9(6) . . . . ? C4B C3B N7B C8B -27.9(9) . . . . ? C2B C3B N7B C8B 155.4(6) . . . . ? C4B C3B N7B C11B 147.1(5) . . . . ? C2B C3B N7B C11B -29.6(7) . . . . ? C11B N7B C8B C9B -3.3(8) . . . . ? C3B N7B C8B C9B 172.4(6) . . . . ? N7B C8B C9B C10B 3.2(10) . . . . ? C8B C9B C10B C11B -1.8(10) . . . . ? C9B C10B C11B N7B -0.2(9) . . . . ? C8B N7B C11B C10B 2.2(8) . . . . ? C3B N7B C11B C10B -173.7(6) . . . . ? O1C C1C C2C O2C -54.5(5) . . . . ? C6C C1C C2C O2C 75.4(4) . . . . ? O1C C1C C2C C3C -174.6(4) . . . . ? C6C C1C C2C C3C -44.7(5) . . . . ? O2C C2C C3C C4C -91.0(5) . . . . ? C1C C2C C3C C4C 30.3(6) . . . . ? O2C C2C C3C N7C 81.1(5) . . . . ? C1C C2C C3C N7C -157.5(4) . . . . ? N7C C3C C4C C5C -174.6(5) . . . . ? C2C C3C C4C C5C -2.8(7) . . . . ? C3C C4C C5C C6C -11.4(8) . . . . ? C4C C5C C6C C1C -5.2(8) . . . . ? O1C C1C C6C C5C 163.8(4) . . . . ? C2C C1C C6C C5C 34.2(6) . . . . ? C4C C3C N7C C11C -153.2(5) . . . . ? C2C C3C N7C C11C 35.0(6) . . . . ? C4C C3C N7C C8C 22.2(7) . . . . ? C2C C3C N7C C8C -149.7(5) . . . . ? C11C N7C C8C C9C -0.4(6) . . . . ? C3C N7C C8C C9C -176.5(4) . . . . ? N7C C8C C9C C10C 0.4(6) . . . . ? C8C C9C C10C C11C -0.2(7) . . . . ? C9C C10C C11C N7C -0.1(6) . . . . ? C8C N7C C11C C10C 0.3(6) . . . . ? C3C N7C C11C C10C 176.3(5) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 55.05 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.309 _refine_diff_density_min -0.253 _refine_diff_density_rms 0.061 # Attachment '2g1.cif' data_2g _database_code_depnum_ccdc_archive 'CCDC 691142' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H13 N O2' _chemical_formula_sum 'C11 H13 N O2' _chemical_formula_weight 191.22 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 15.561(6) _cell_length_b 6.152(2) _cell_length_c 11.984(6) _cell_angle_alpha 90.00 _cell_angle_beta 122.08(3) _cell_angle_gamma 90.00 _cell_volume 972.0(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prisms _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.307 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.732 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens P3 diffractometer' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 2214 _diffrn_reflns_av_R_equivalents 0.0365 _diffrn_reflns_av_sigmaI/netI 0.0324 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 4.35 _diffrn_reflns_theta_max 49.99 _reflns_number_total 997 _reflns_number_gt 987 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens P3/V2000' _computing_cell_refinement 'Siemens P3/V2000' _computing_data_reduction 'Siemens P3/V2000' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0538P)^2^+0.1508P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0046(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _chemical_absolute_configuration ad _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.07(17) _refine_ls_number_reflns 997 _refine_ls_number_parameters 130 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0324 _refine_ls_R_factor_gt 0.0321 _refine_ls_wR_factor_ref 0.0848 _refine_ls_wR_factor_gt 0.0844 _refine_ls_goodness_of_fit_ref 1.141 _refine_ls_restrained_S_all 1.140 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.001 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 C1 C 0.89980(17) 0.6866(4) 0.6049(2) 0.0455(7) Uani 1 1 d . . . H1 H 0.8517 0.7267 0.6305 0.055 Uiso 1 1 calc R . . O1 O 0.88378(13) 0.8327(3) 0.50396(15) 0.0594(6) Uani 1 1 d . . . H1A H 0.9089 0.7824 0.4643 0.089 Uiso 1 1 calc R . . C2 C 1.00574(15) 0.7113(4) 0.7272(2) 0.0391(6) Uani 1 1 d . . . H2 H 1.0137 0.8593 0.7617 0.047 Uiso 1 1 calc R . . O2 O 1.07821(11) 0.6762(3) 0.68973(15) 0.0511(5) Uani 1 1 d . . . H2A H 1.1297 0.7464 0.7383 0.077 Uiso 1 1 calc R . . C3 C 1.02398(17) 0.5517(4) 0.8323(2) 0.0406(7) Uani 1 1 d . . . C4 C 0.96982(19) 0.3678(4) 0.8022(3) 0.0520(8) Uani 1 1 d . . . H4 H 0.9881 0.2681 0.8696 0.062 Uiso 1 1 calc R . . C5 C 0.88210(18) 0.3119(5) 0.6681(2) 0.0554(7) Uani 1 1 d . . . H5A H 0.8195 0.3309 0.6662 0.066 Uiso 1 1 calc R . . H5B H 0.8868 0.1603 0.6497 0.066 Uiso 1 1 calc R . . C6 C 0.87916(17) 0.4528(5) 0.5615(2) 0.0522(8) Uani 1 1 d . . . H6A H 0.9297 0.4020 0.5436 0.063 Uiso 1 1 calc R . . H6B H 0.8130 0.4409 0.4809 0.063 Uiso 1 1 calc R . . C7 C 1.11165(16) 0.5945(4) 0.9681(2) 0.0356(6) Uani 1 1 d . . . C8 C 1.18298(18) 0.4366(5) 1.0390(2) 0.0463(7) Uani 1 1 d . . . H8 H 1.1748 0.3022 0.9990 0.056 Uiso 1 1 calc R . . N9 N 1.26325(15) 0.4630(4) 1.1612(2) 0.0560(7) Uani 1 1 d . . . C10 C 1.2746(2) 0.6555(5) 1.2174(2) 0.0585(8) Uani 1 1 d . . . H10 H 1.3298 0.6759 1.3027 0.070 Uiso 1 1 calc R . . C11 C 1.20959(19) 0.8250(5) 1.1564(2) 0.0540(7) Uani 1 1 d . . . H11 H 1.2202 0.9578 1.1990 0.065 Uiso 1 1 calc R . . C12 C 1.12751(18) 0.7945(5) 1.0296(2) 0.0472(7) Uani 1 1 d . . . H12 H 1.0828 0.9085 0.9855 0.057 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 C1 0.0335(14) 0.0612(18) 0.0296(14) 0.0028(14) 0.0085(11) 0.0093(13) O1 0.0523(11) 0.0773(13) 0.0343(10) 0.0090(9) 0.0134(8) 0.0185(10) C2 0.0342(13) 0.0446(14) 0.0286(13) -0.0014(12) 0.0101(10) 0.0057(12) O2 0.0342(9) 0.0717(12) 0.0391(9) -0.0062(8) 0.0138(7) -0.0095(9) C3 0.0302(13) 0.0451(17) 0.0344(14) 0.0005(11) 0.0090(11) 0.0041(13) C4 0.0450(14) 0.0493(19) 0.0475(15) 0.0024(13) 0.0150(13) -0.0027(15) C5 0.0390(14) 0.0517(16) 0.0605(17) -0.0095(14) 0.0163(13) -0.0052(14) C6 0.0272(13) 0.0704(19) 0.0367(15) -0.0160(14) 0.0020(11) -0.0055(15) C7 0.0275(14) 0.0429(15) 0.0320(13) 0.0042(13) 0.0128(12) 0.0023(12) C8 0.0439(15) 0.0541(16) 0.0369(15) 0.0015(12) 0.0188(13) 0.0072(13) N9 0.0424(13) 0.0786(18) 0.0322(13) 0.0055(12) 0.0098(11) 0.0171(13) C10 0.0445(15) 0.084(2) 0.0287(14) -0.0038(16) 0.0070(12) 0.0029(16) C11 0.0532(16) 0.0595(17) 0.0386(15) -0.0040(14) 0.0172(14) -0.0020(16) C12 0.0369(14) 0.0531(19) 0.0384(14) 0.0056(15) 0.0110(12) 0.0036(13) _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 O1 1.419(3) . ? C1 C6 1.505(4) . ? C1 C2 1.524(3) . ? C2 O2 1.434(3) . ? C2 C3 1.501(3) . ? C3 C4 1.340(4) . ? C3 C7 1.491(3) . ? C4 C5 1.495(4) . ? C5 C6 1.524(4) . ? C7 C8 1.377(4) . ? C7 C12 1.387(4) . ? C8 N9 1.338(3) . ? N9 C10 1.326(4) . ? C10 C11 1.364(4) . ? C11 C12 1.383(3) . ? 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 O1 C1 C6 113.7(2) . . ? O1 C1 C2 111.5(2) . . ? C6 C1 C2 110.5(2) . . ? O2 C2 C3 109.54(19) . . ? O2 C2 C1 108.23(18) . . ? C3 C2 C1 111.6(2) . . ? C4 C3 C7 121.5(2) . . ? C4 C3 C2 121.0(2) . . ? C7 C3 C2 117.1(2) . . ? C3 C4 C5 124.6(2) . . ? C4 C5 C6 112.0(2) . . ? C1 C6 C5 110.4(2) . . ? C8 C7 C12 116.1(2) . . ? C8 C7 C3 121.3(2) . . ? C12 C7 C3 122.6(2) . . ? N9 C8 C7 124.6(3) . . ? C10 N9 C8 117.3(2) . . ? N9 C10 C11 123.4(2) . . ? C10 C11 C12 118.3(3) . . ? C11 C12 C7 120.3(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 O2 -57.5(3) . . . . ? C6 C1 C2 O2 70.1(3) . . . . ? O1 C1 C2 C3 -178.08(19) . . . . ? C6 C1 C2 C3 -50.5(3) . . . . ? O2 C2 C3 C4 -97.3(3) . . . . ? C1 C2 C3 C4 22.5(3) . . . . ? O2 C2 C3 C7 76.2(2) . . . . ? C1 C2 C3 C7 -164.0(2) . . . . ? C7 C3 C4 C5 -179.0(2) . . . . ? C2 C3 C4 C5 -5.7(4) . . . . ? C3 C4 C5 C6 16.3(4) . . . . ? O1 C1 C6 C5 -171.25(19) . . . . ? C2 C1 C6 C5 62.4(3) . . . . ? C4 C5 C6 C1 -43.8(3) . . . . ? C4 C3 C7 C8 45.0(3) . . . . ? C2 C3 C7 C8 -128.5(2) . . . . ? C4 C3 C7 C12 -136.2(3) . . . . ? C2 C3 C7 C12 50.3(3) . . . . ? C12 C7 C8 N9 1.4(3) . . . . ? C3 C7 C8 N9 -179.7(2) . . . . ? C7 C8 N9 C10 -0.3(4) . . . . ? C8 N9 C10 C11 -0.5(4) . . . . ? N9 C10 C11 C12 0.1(4) . . . . ? C10 C11 C12 C7 1.1(4) . . . . ? C8 C7 C12 C11 -1.8(3) . . . . ? C3 C7 C12 C11 179.4(2) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 49.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.110 _refine_diff_density_min -0.124 _refine_diff_density_rms 0.033