# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_cd212705 #TrackingRef 'cd212705.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H9 N O2' _chemical_formula_weight 199.20 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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 8.1053(9) _cell_length_b 14.1123(16) _cell_length_c 9.2252(11) _cell_angle_alpha 90.00 _cell_angle_beta 97.664(2) _cell_angle_gamma 90.00 _cell_volume 1045.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2033 _cell_measurement_theta_min 5.309 _cell_measurement_theta_max 52.129 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.311 _exptl_crystal_size_mid 0.186 _exptl_crystal_size_min 0.079 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.265 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.46885 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 6223 _diffrn_reflns_av_R_equivalents 0.0301 _diffrn_reflns_av_sigmaI/netI 0.0306 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.65 _diffrn_reflns_theta_max 25.99 _reflns_number_total 2051 _reflns_number_gt 1738 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0576P)^2^+0.2405P] 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 2051 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0551 _refine_ls_R_factor_gt 0.0475 _refine_ls_wR_factor_ref 0.1225 _refine_ls_wR_factor_gt 0.1163 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _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 0.0067(2) 0.02734(10) 0.77292(18) 0.0663(4) Uani 1 1 d . . . O1 O 0.12837(18) 0.39961(8) 0.86778(13) 0.0702(4) Uani 1 1 d . . . O2 O 0.17670(14) 0.33127(7) 1.08720(11) 0.0536(3) Uani 1 1 d . . . C1 C 0.15798(18) 0.15796(10) 0.64642(16) 0.0438(4) Uani 1 1 d . . . C2 C 0.1583(2) 0.15066(13) 0.49574(18) 0.0597(5) Uani 1 1 d . . . H2 H 0.1074 0.0992 0.4450 0.072 Uiso 1 1 calc R . . C3 C 0.2336(3) 0.21920(15) 0.42237(18) 0.0702(6) Uani 1 1 d . . . H3 H 0.2342 0.2144 0.3219 0.084 Uiso 1 1 calc R . . C4 C 0.3082(2) 0.29507(14) 0.4980(2) 0.0672(5) Uani 1 1 d . . . H4 H 0.3595 0.3414 0.4480 0.081 Uiso 1 1 calc R . . C5 C 0.3082(2) 0.30351(12) 0.64680(18) 0.0539(4) Uani 1 1 d . . . H5 H 0.3585 0.3558 0.6958 0.065 Uiso 1 1 calc R . . C6 C 0.23395(17) 0.23487(10) 0.72442(15) 0.0402(3) Uani 1 1 d . . . C7 C 0.23504(17) 0.24288(9) 0.88535(15) 0.0395(3) Uani 1 1 d . . . C8 C 0.28409(19) 0.17262(10) 0.97395(16) 0.0464(4) Uani 1 1 d . . . C9 C 0.3306(3) 0.10271(14) 1.0594(2) 0.0705(6) Uani 1 1 d . . . C10 C 0.07512(19) 0.08534(11) 0.71933(18) 0.0484(4) Uani 1 1 d . . . C11 C 0.17529(18) 0.33312(10) 0.94329(15) 0.0430(4) Uani 1 1 d . . . C12 C 0.1054(2) 0.41270(12) 1.15030(19) 0.0574(4) Uani 1 1 d . . . H12A H 0.1744 0.4671 1.1415 0.086 Uiso 1 1 calc R . . H12B H 0.0983 0.4008 1.2517 0.086 Uiso 1 1 calc R . . H12C H -0.0041 0.4243 1.0996 0.086 Uiso 1 1 calc R . . H9A H 0.448(3) 0.0968(16) 1.102(3) 0.090(7) Uiso 1 1 d . . . H9B H 0.252(3) 0.0559(17) 1.078(3) 0.100(8) Uiso 1 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 N1 0.0653(9) 0.0483(8) 0.0850(11) -0.0052(7) 0.0087(8) -0.0086(7) O1 0.1064(11) 0.0522(7) 0.0541(7) 0.0083(5) 0.0181(7) 0.0245(7) O2 0.0718(7) 0.0484(6) 0.0390(6) -0.0063(4) 0.0018(5) 0.0082(5) C1 0.0445(8) 0.0442(8) 0.0421(8) -0.0053(6) 0.0030(6) 0.0079(6) C2 0.0648(11) 0.0673(11) 0.0449(9) -0.0133(8) -0.0008(8) 0.0145(8) C3 0.0832(13) 0.0920(14) 0.0364(9) 0.0032(9) 0.0122(9) 0.0250(11) C4 0.0693(12) 0.0794(13) 0.0572(11) 0.0247(10) 0.0238(9) 0.0130(10) C5 0.0577(10) 0.0523(9) 0.0531(9) 0.0071(7) 0.0123(8) -0.0006(7) C6 0.0414(7) 0.0407(7) 0.0385(8) 0.0010(6) 0.0049(6) 0.0047(6) C7 0.0425(7) 0.0371(7) 0.0381(7) -0.0006(6) 0.0029(6) -0.0044(6) C8 0.0549(9) 0.0442(8) 0.0390(8) -0.0044(6) 0.0021(7) -0.0024(7) C9 0.0941(16) 0.0567(11) 0.0561(11) 0.0099(8) -0.0068(11) 0.0071(11) C10 0.0479(8) 0.0415(8) 0.0543(9) -0.0120(7) 0.0008(7) 0.0020(7) C11 0.0473(8) 0.0414(8) 0.0395(8) -0.0011(6) 0.0031(6) -0.0029(6) C12 0.0655(10) 0.0553(9) 0.0514(9) -0.0141(7) 0.0078(8) 0.0063(8) _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 C10 1.138(2) . ? O1 C11 1.1999(17) . ? O2 C11 1.3264(17) . ? O2 C12 1.4434(18) . ? C1 C2 1.394(2) . ? C1 C6 1.399(2) . ? C1 C10 1.440(2) . ? C2 C3 1.370(3) . ? C2 H2 0.9300 . ? C3 C4 1.373(3) . ? C3 H3 0.9300 . ? C4 C5 1.378(2) . ? C4 H4 0.9300 . ? C5 C6 1.388(2) . ? C5 H5 0.9300 . ? C6 C7 1.4878(19) . ? C7 C8 1.312(2) . ? C7 C11 1.4869(19) . ? C8 C9 1.288(2) . ? C9 H9A 0.98(2) . ? C9 H9B 0.95(2) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? 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 C11 O2 C12 115.95(12) . . ? C2 C1 C6 120.73(15) . . ? C2 C1 C10 118.42(14) . . ? C6 C1 C10 120.84(13) . . ? C3 C2 C1 120.04(16) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C2 C3 C4 119.63(15) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C3 C4 C5 121.00(17) . . ? C3 C4 H4 119.5 . . ? C5 C4 H4 119.5 . . ? C4 C5 C6 120.73(17) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C5 C6 C1 117.86(13) . . ? C5 C6 C7 121.08(13) . . ? C1 C6 C7 121.06(12) . . ? C8 C7 C11 120.61(13) . . ? C8 C7 C6 121.67(13) . . ? C11 C7 C6 117.71(12) . . ? C9 C8 C7 179.02(18) . . ? C8 C9 H9A 120.0(14) . . ? C8 C9 H9B 119.7(15) . . ? H9A C9 H9B 120(2) . . ? N1 C10 C1 177.88(17) . . ? O1 C11 O2 123.79(13) . . ? O1 C11 C7 123.66(13) . . ? O2 C11 C7 112.54(12) . . ? O2 C12 H12A 109.5 . . ? O2 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O2 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 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 C6 C1 C2 C3 0.0(2) . . . . ? C10 C1 C2 C3 178.96(15) . . . . ? C1 C2 C3 C4 -0.2(3) . . . . ? C2 C3 C4 C5 -0.2(3) . . . . ? C3 C4 C5 C6 0.6(3) . . . . ? C4 C5 C6 C1 -0.7(2) . . . . ? C4 C5 C6 C7 179.31(14) . . . . ? C2 C1 C6 C5 0.4(2) . . . . ? C10 C1 C6 C5 -178.49(13) . . . . ? C2 C1 C6 C7 -179.63(13) . . . . ? C10 C1 C6 C7 1.5(2) . . . . ? C5 C6 C7 C8 -129.23(16) . . . . ? C1 C6 C7 C8 50.8(2) . . . . ? C5 C6 C7 C11 51.90(19) . . . . ? C1 C6 C7 C11 -128.05(14) . . . . ? C11 C7 C8 C9 131(12) . . . . ? C6 C7 C8 C9 -48(12) . . . . ? C2 C1 C10 N1 -23(5) . . . . ? C6 C1 C10 N1 156(4) . . . . ? C12 O2 C11 O1 4.6(2) . . . . ? C12 O2 C11 C7 -174.20(13) . . . . ? C8 C7 C11 O1 -179.71(16) . . . . ? C6 C7 C11 O1 -0.8(2) . . . . ? C8 C7 C11 O2 -0.9(2) . . . . ? C6 C7 C11 O2 177.98(12) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.181 _refine_diff_density_min -0.233 _refine_diff_density_rms 0.043 _database_code_depnum_ccdc_archive 'CCDC 917097'