# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'RSC Advances' _journal_coden_Cambridge 1500 _journal_year 2012 _journal_volume 2 _journal_page_first 1 _publ_contact_author_name 'Dr Changsheng Yao' _publ_contact_author_email csyao@xznu.edu.cn _publ_section_title ; One-pot Solvent-free Synthesis of Quinolines by C-H Activation / C-C Bond Formation Catalyzed by Recyclable Iron(III) Triflate ; loop_ _publ_author_name 'Changsheng Yao' 'Bingbin Qin' 'Honghong Zhang' 'Jun Lu' 'Donglin Wang' 'Shujiang Tu' # Attachment '- CCDC 842657.cif' data_101127a _database_code_depnum_ccdc_archive 'CCDC 842657' #TrackingRef '- CCDC 842657.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H15 Cl2 N' _chemical_formula_weight 364.25 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' Cl Cl 0.1484 0.1585 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/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 8.486(3) _cell_length_b 15.397(5) _cell_length_c 14.367(4) _cell_angle_alpha 90.00 _cell_angle_beta 111.573(15) _cell_angle_gamma 90.00 _cell_volume 1745.7(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5726 _cell_measurement_theta_min 2.581 _cell_measurement_theta_max 29.816 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.386 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 0.375 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.896 _exptl_absorpt_correction_T_max 0.925 _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 12183 _diffrn_reflns_av_R_equivalents 0.0341 _diffrn_reflns_av_sigmaI/netI 0.0382 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 30.62 _reflns_number_total 4668 _reflns_number_gt 3443 _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^)+(0.0858P)^2^+0.2832P] 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 4668 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0686 _refine_ls_R_factor_gt 0.0461 _refine_ls_wR_factor_ref 0.1610 _refine_ls_wR_factor_gt 0.1347 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.084 _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 Cl1 Cl 0.05419(7) 0.56445(5) -0.38657(3) 0.0768(2) Uani 1 1 d . . . Cl2 Cl 0.32757(9) 0.71157(4) -0.35536(4) 0.0747(2) Uani 1 1 d . . . N1 N 0.17811(18) 0.45067(10) -0.02826(10) 0.0463(3) Uani 1 1 d . . . C1 C 0.2674(2) 0.52294(11) -0.00581(11) 0.0423(3) Uani 1 1 d . . . C2 C 0.3388(2) 0.55451(11) 0.09290(12) 0.0451(4) Uani 1 1 d . . . H2 H 0.3991 0.6064 0.1053 0.054 Uiso 1 1 calc R . . C3 C 0.3212(2) 0.51029(11) 0.17049(11) 0.0429(3) Uani 1 1 d . . . C4 C 0.2335(2) 0.42965(11) 0.14937(12) 0.0425(3) Uani 1 1 d . . . C5 C 0.2189(2) 0.37289(12) 0.22277(13) 0.0508(4) Uani 1 1 d . . . H5 H 0.2684 0.3885 0.2898 0.061 Uiso 1 1 calc R . . C6 C 0.1345(3) 0.29581(13) 0.19839(15) 0.0568(4) Uani 1 1 d . . . C7 C 0.0565(3) 0.27401(13) 0.09650(17) 0.0613(5) Uani 1 1 d . . . H7 H -0.0055 0.2228 0.0788 0.074 Uiso 1 1 calc R . . C8 C 0.0696(3) 0.32581(13) 0.02414(15) 0.0559(4) Uani 1 1 d . . . H8 H 0.0172 0.3096 -0.0425 0.067 Uiso 1 1 calc R . . C9 C 0.1615(2) 0.40419(11) 0.04784(12) 0.0449(4) Uani 1 1 d . . . C10 C 0.3909(2) 0.54693(11) 0.27262(12) 0.0458(4) Uani 1 1 d . . . C11 C 0.5587(3) 0.57181(12) 0.31465(15) 0.0562(4) Uani 1 1 d . . . H11 H 0.6291 0.5653 0.2785 0.067 Uiso 1 1 calc R . . C12 C 0.6225(3) 0.60628(15) 0.41004(16) 0.0710(6) Uani 1 1 d . . . H12 H 0.7358 0.6225 0.4380 0.085 Uiso 1 1 calc R . . C13 C 0.5193(4) 0.61670(14) 0.46389(14) 0.0718(6) Uani 1 1 d . . . H13 H 0.5631 0.6394 0.5284 0.086 Uiso 1 1 calc R . . C14 C 0.3528(4) 0.59374(15) 0.42266(15) 0.0703(6) Uani 1 1 d . . . H14 H 0.2824 0.6014 0.4587 0.084 Uiso 1 1 calc R . . C15 C 0.2887(3) 0.55913(13) 0.32764(15) 0.0599(5) Uani 1 1 d . . . H15 H 0.1748 0.5437 0.3000 0.072 Uiso 1 1 calc R . . C16 C 0.2848(2) 0.57105(11) -0.09070(11) 0.0421(3) Uani 1 1 d . . . C17 C 0.1794(2) 0.54966(12) -0.18720(12) 0.0475(4) Uani 1 1 d . . . H17 H 0.0999 0.5056 -0.1973 0.057 Uiso 1 1 calc R . . C18 C 0.1908(2) 0.59289(13) -0.26834(12) 0.0499(4) Uani 1 1 d . . . C19 C 0.3092(2) 0.65761(12) -0.25497(13) 0.0501(4) Uani 1 1 d . . . C20 C 0.4160(3) 0.67896(13) -0.15943(15) 0.0553(4) Uani 1 1 d . . . H20 H 0.4970 0.7222 -0.1498 0.066 Uiso 1 1 calc R . . C21 C 0.4032(2) 0.63640(12) -0.07829(13) 0.0520(4) Uani 1 1 d . . . H21 H 0.4751 0.6517 -0.0141 0.062 Uiso 1 1 calc R . . C22 C 0.1238(4) 0.23508(16) 0.27780(19) 0.0798(7) Uani 1 1 d . . . H22A H 0.1965 0.1860 0.2831 0.120 Uiso 1 1 calc R . . H22B H 0.0091 0.2155 0.2601 0.120 Uiso 1 1 calc R . . H22C H 0.1590 0.2649 0.3408 0.120 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 Cl1 0.0698(4) 0.1122(5) 0.0344(2) 0.0020(2) 0.0027(2) -0.0116(3) Cl2 0.0979(5) 0.0746(4) 0.0535(3) 0.0134(2) 0.0300(3) -0.0014(3) N1 0.0457(7) 0.0534(8) 0.0378(7) -0.0077(6) 0.0132(6) -0.0007(6) C1 0.0408(7) 0.0482(9) 0.0354(7) -0.0045(6) 0.0110(6) 0.0057(6) C2 0.0482(8) 0.0470(9) 0.0385(8) -0.0068(6) 0.0140(7) 0.0001(7) C3 0.0416(8) 0.0499(9) 0.0339(7) -0.0069(6) 0.0102(6) 0.0046(6) C4 0.0406(8) 0.0494(9) 0.0365(7) -0.0042(6) 0.0130(6) 0.0051(6) C5 0.0552(10) 0.0556(10) 0.0429(8) -0.0023(7) 0.0194(7) 0.0039(8) C6 0.0631(11) 0.0538(10) 0.0590(11) 0.0007(8) 0.0289(9) 0.0021(8) C7 0.0686(12) 0.0532(11) 0.0663(12) -0.0121(9) 0.0298(10) -0.0114(9) C8 0.0608(11) 0.0572(11) 0.0491(9) -0.0153(8) 0.0196(8) -0.0092(8) C9 0.0438(8) 0.0509(9) 0.0387(8) -0.0066(6) 0.0136(7) 0.0021(7) C10 0.0522(9) 0.0468(9) 0.0334(7) -0.0023(6) 0.0100(7) 0.0012(7) C11 0.0534(10) 0.0589(11) 0.0479(10) -0.0018(8) 0.0086(8) 0.0030(8) C12 0.0654(12) 0.0667(13) 0.0543(11) -0.0042(9) -0.0092(9) -0.0040(10) C13 0.1071(18) 0.0609(12) 0.0327(8) -0.0050(8) 0.0084(10) -0.0041(12) C14 0.1013(18) 0.0713(13) 0.0433(10) -0.0107(9) 0.0324(11) -0.0047(12) C15 0.0645(12) 0.0701(12) 0.0469(10) -0.0145(8) 0.0227(9) -0.0079(9) C16 0.0403(8) 0.0508(9) 0.0337(7) -0.0051(6) 0.0118(6) 0.0057(6) C17 0.0430(8) 0.0592(10) 0.0361(8) -0.0024(7) 0.0095(6) 0.0006(7) C18 0.0461(9) 0.0631(10) 0.0348(7) 0.0001(7) 0.0083(6) 0.0080(8) C19 0.0589(10) 0.0513(9) 0.0416(8) 0.0027(7) 0.0203(8) 0.0107(8) C20 0.0630(11) 0.0532(10) 0.0517(10) -0.0072(8) 0.0233(9) -0.0057(8) C21 0.0556(10) 0.0590(10) 0.0391(8) -0.0099(7) 0.0149(7) -0.0041(8) C22 0.1063(19) 0.0646(13) 0.0762(15) 0.0053(11) 0.0425(15) -0.0083(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 Cl1 C18 1.7242(18) . ? Cl2 C19 1.7206(18) . ? N1 C1 1.318(2) . ? N1 C9 1.357(2) . ? C1 C2 1.408(2) . ? C1 C16 1.480(2) . ? C2 C3 1.361(2) . ? C2 H2 0.9300 . ? C3 C4 1.422(2) . ? C3 C10 1.477(2) . ? C4 C5 1.410(2) . ? C4 C9 1.414(2) . ? C5 C6 1.364(3) . ? C5 H5 0.9300 . ? C6 C7 1.408(3) . ? C6 C22 1.503(3) . ? C7 C8 1.347(3) . ? C7 H7 0.9300 . ? C8 C9 1.409(3) . ? C8 H8 0.9300 . ? C10 C11 1.381(3) . ? C10 C15 1.384(3) . ? C11 C12 1.381(3) . ? C11 H11 0.9300 . ? C12 C13 1.374(4) . ? C12 H12 0.9300 . ? C13 C14 1.363(4) . ? C13 H13 0.9300 . ? C14 C15 1.378(3) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C17 1.385(2) . ? C16 C21 1.386(3) . ? C17 C18 1.377(2) . ? C17 H17 0.9300 . ? C18 C19 1.377(3) . ? C19 C20 1.378(3) . ? C20 C21 1.376(3) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 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 C1 N1 C9 117.96(14) . . ? N1 C1 C2 122.28(15) . . ? N1 C1 C16 116.33(14) . . ? C2 C1 C16 121.37(15) . . ? C3 C2 C1 121.06(16) . . ? C3 C2 H2 119.5 . . ? C1 C2 H2 119.5 . . ? C2 C3 C4 117.95(14) . . ? C2 C3 C10 119.87(15) . . ? C4 C3 C10 122.18(15) . . ? C5 C4 C9 118.45(16) . . ? C5 C4 C3 124.38(15) . . ? C9 C4 C3 117.13(15) . . ? C6 C5 C4 121.98(17) . . ? C6 C5 H5 119.0 . . ? C4 C5 H5 119.0 . . ? C5 C6 C7 118.46(18) . . ? C5 C6 C22 121.3(2) . . ? C7 C6 C22 120.3(2) . . ? C8 C7 C6 121.36(18) . . ? C8 C7 H7 119.3 . . ? C6 C7 H7 119.3 . . ? C7 C8 C9 121.08(18) . . ? C7 C8 H8 119.5 . . ? C9 C8 H8 119.5 . . ? N1 C9 C8 117.99(15) . . ? N1 C9 C4 123.48(15) . . ? C8 C9 C4 118.52(16) . . ? C11 C10 C15 118.33(16) . . ? C11 C10 C3 120.80(16) . . ? C15 C10 C3 120.85(16) . . ? C10 C11 C12 120.4(2) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C13 C12 C11 120.4(2) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C14 C13 C12 119.90(18) . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C13 C14 C15 120.0(2) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C14 C15 C10 121.1(2) . . ? C14 C15 H15 119.5 . . ? C10 C15 H15 119.4 . . ? C17 C16 C21 118.17(16) . . ? C17 C16 C1 118.84(15) . . ? C21 C16 C1 122.99(14) . . ? C18 C17 C16 120.79(17) . . ? C18 C17 H17 119.6 . . ? C16 C17 H17 119.6 . . ? C17 C18 C19 120.45(16) . . ? C17 C18 Cl1 118.69(15) . . ? C19 C18 Cl1 120.86(14) . . ? C18 C19 C20 119.37(17) . . ? C18 C19 Cl2 121.25(14) . . ? C20 C19 Cl2 119.38(15) . . ? C21 C20 C19 120.15(18) . . ? C21 C20 H20 119.9 . . ? C19 C20 H20 119.9 . . ? C20 C21 C16 121.06(16) . . ? C20 C21 H21 119.5 . . ? C16 C21 H21 119.5 . . ? C6 C22 H22A 109.5 . . ? C6 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C6 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 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 C9 N1 C1 C2 -2.6(2) . . . . ? C9 N1 C1 C16 179.06(14) . . . . ? N1 C1 C2 C3 1.3(3) . . . . ? C16 C1 C2 C3 179.46(15) . . . . ? C1 C2 C3 C4 2.2(2) . . . . ? C1 C2 C3 C10 -177.25(15) . . . . ? C2 C3 C4 C5 173.80(16) . . . . ? C10 C3 C4 C5 -6.8(2) . . . . ? C2 C3 C4 C9 -4.0(2) . . . . ? C10 C3 C4 C9 175.43(15) . . . . ? C9 C4 C5 C6 -1.6(3) . . . . ? C3 C4 C5 C6 -179.39(16) . . . . ? C4 C5 C6 C7 -1.6(3) . . . . ? C4 C5 C6 C22 178.53(19) . . . . ? C5 C6 C7 C8 2.7(3) . . . . ? C22 C6 C7 C8 -177.5(2) . . . . ? C6 C7 C8 C9 -0.4(3) . . . . ? C1 N1 C9 C8 -178.46(15) . . . . ? C1 N1 C9 C4 0.6(2) . . . . ? C7 C8 C9 N1 176.17(18) . . . . ? C7 C8 C9 C4 -2.9(3) . . . . ? C5 C4 C9 N1 -175.19(15) . . . . ? C3 C4 C9 N1 2.8(2) . . . . ? C5 C4 C9 C8 3.9(2) . . . . ? C3 C4 C9 C8 -178.21(15) . . . . ? C2 C3 C10 C11 -53.6(2) . . . . ? C4 C3 C10 C11 126.99(18) . . . . ? C2 C3 C10 C15 124.9(2) . . . . ? C4 C3 C10 C15 -54.6(2) . . . . ? C15 C10 C11 C12 1.3(3) . . . . ? C3 C10 C11 C12 179.77(18) . . . . ? C10 C11 C12 C13 -0.4(3) . . . . ? C11 C12 C13 C14 -0.7(3) . . . . ? C12 C13 C14 C15 0.8(4) . . . . ? C13 C14 C15 C10 0.1(4) . . . . ? C11 C10 C15 C14 -1.1(3) . . . . ? C3 C10 C15 C14 -179.62(19) . . . . ? N1 C1 C16 C17 14.2(2) . . . . ? C2 C1 C16 C17 -164.14(15) . . . . ? N1 C1 C16 C21 -165.28(16) . . . . ? C2 C1 C16 C21 16.4(2) . . . . ? C21 C16 C17 C18 -0.7(3) . . . . ? C1 C16 C17 C18 179.81(15) . . . . ? C16 C17 C18 C19 0.8(3) . . . . ? C16 C17 C18 Cl1 -179.09(13) . . . . ? C17 C18 C19 C20 -0.2(3) . . . . ? Cl1 C18 C19 C20 179.75(15) . . . . ? C17 C18 C19 Cl2 179.18(14) . . . . ? Cl1 C18 C19 Cl2 -0.9(2) . . . . ? C18 C19 C20 C21 -0.6(3) . . . . ? Cl2 C19 C20 C21 -179.92(14) . . . . ? C19 C20 C21 C16 0.7(3) . . . . ? C17 C16 C21 C20 0.0(3) . . . . ? C1 C16 C21 C20 179.43(16) . . . . ? _diffrn_measured_fraction_theta_max 0.867 _diffrn_reflns_theta_full 30.62 _diffrn_measured_fraction_theta_full 0.867 _refine_diff_density_max 0.302 _refine_diff_density_min -0.441 _refine_diff_density_rms 0.069 # Attachment '- CCDC 842682.cif' data_b _database_code_depnum_ccdc_archive 'CCDC 842682' #TrackingRef '- CCDC 842682.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H15 N O' _chemical_formula_weight 297.34 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 P21/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 13.740(2) _cell_length_b 7.0021(12) _cell_length_c 15.550(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.820(4) _cell_angle_gamma 90.00 _cell_volume 1488.3(4) _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 block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.327 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.081 _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 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 7918 _diffrn_reflns_av_R_equivalents 0.0312 _diffrn_reflns_av_sigmaI/netI 0.0313 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.63 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2612 _reflns_number_gt 1959 _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^)+(0.0699P)^2^+0.0961P] 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 SHELXL _refine_ls_extinction_coef 0.026(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2612 _refine_ls_number_parameters 213 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0592 _refine_ls_R_factor_gt 0.0409 _refine_ls_wR_factor_ref 0.1271 _refine_ls_wR_factor_gt 0.1155 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _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 C11 C 0.62001(11) 0.40369(19) 0.26284(10) 0.0560(4) Uani 1 1 d . . . C10 C 0.53340(10) 0.39772(17) 0.30439(9) 0.0471(3) Uani 1 1 d . . . C15 C 0.54439(11) 0.3878(2) 0.39445(9) 0.0549(4) Uani 1 1 d . . . H15A H 0.4886 0.3819 0.4235 0.066 Uiso 1 1 calc R . . C14 C 0.63390(11) 0.3865(2) 0.44173(10) 0.0628(4) Uani 1 1 d . . . H14A H 0.6384 0.3784 0.5017 0.075 Uiso 1 1 calc R . . C13 C 0.71722(12) 0.3972(2) 0.39982(12) 0.0684(5) Uani 1 1 d . . . H13A H 0.7784 0.3983 0.4315 0.082 Uiso 1 1 calc R . . C12 C 0.71012(12) 0.4061(2) 0.31158(12) 0.0685(5) Uani 1 1 d . . . H12A H 0.7668 0.4140 0.2838 0.082 Uiso 1 1 calc R . . C1 C 0.43642(10) 0.40147(17) 0.25474(8) 0.0462(3) Uani 1 1 d . . . C2 C 0.34912(10) 0.41519(17) 0.29564(8) 0.0474(3) Uani 1 1 d . . . H2A H 0.3531 0.4221 0.3556 0.057 Uiso 1 1 calc R . . C3 C 0.25980(10) 0.41844(18) 0.24941(8) 0.0474(3) Uani 1 1 d . . . C4 C 0.25483(11) 0.40761(18) 0.15723(8) 0.0497(4) Uani 1 1 d . . . C9 C 0.34464(12) 0.39781(17) 0.12017(9) 0.0515(4) Uani 1 1 d . . . C8 C 0.34394(13) 0.3944(2) 0.02950(9) 0.0630(4) Uani 1 1 d . . . H8A H 0.4028 0.3895 0.0049 0.076 Uiso 1 1 calc R . . C7 C 0.25880(15) 0.3981(2) -0.02214(10) 0.0719(5) Uani 1 1 d . . . H7A H 0.2596 0.3955 -0.0819 0.086 Uiso 1 1 calc R . . C6 C 0.16978(14) 0.4059(2) 0.01348(10) 0.0707(5) Uani 1 1 d . . . H6A H 0.1115 0.4066 -0.0226 0.085 Uiso 1 1 calc R . . C5 C 0.16760(12) 0.4126(2) 0.10121(9) 0.0613(4) Uani 1 1 d . . . H5A H 0.1078 0.4204 0.1241 0.074 Uiso 1 1 calc R . . C16 C 0.17079(10) 0.4402(2) 0.29551(7) 0.0492(4) Uani 1 1 d . . . C21 C 0.09376(11) 0.3120(2) 0.28485(9) 0.0627(4) Uani 1 1 d . . . H21A H 0.0967 0.2092 0.2474 0.075 Uiso 1 1 calc R . . C20 C 0.01261(11) 0.3355(3) 0.32938(10) 0.0715(5) Uani 1 1 d . . . H20A H -0.0387 0.2486 0.3215 0.086 Uiso 1 1 calc R . . C19 C 0.00735(11) 0.4857(3) 0.38497(10) 0.0726(5) Uani 1 1 d . . . H19A H -0.0476 0.5016 0.4146 0.087 Uiso 1 1 calc R . . C18 C 0.08308(11) 0.6121(2) 0.39678(9) 0.0662(4) Uani 1 1 d . . . H18A H 0.0798 0.7136 0.4349 0.079 Uiso 1 1 calc R . . C17 C 0.16454(10) 0.5906(2) 0.35262(8) 0.0550(4) Uani 1 1 d . . . H17A H 0.2157 0.6777 0.3613 0.066 Uiso 1 1 calc R . . N1 N 0.43288(9) 0.39440(15) 0.16911(7) 0.0514(3) Uani 1 1 d . . . O1 O 0.61852(10) 0.40849(17) 0.17588(7) 0.0745(4) Uani 1 1 d . . . H1 H 0.5477(18) 0.404(3) 0.1545(14) 0.114(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 C11 0.0661(9) 0.0452(8) 0.0600(9) 0.0011(6) 0.0232(7) 0.0021(6) C10 0.0556(8) 0.0360(7) 0.0518(8) -0.0005(5) 0.0149(6) 0.0010(5) C15 0.0581(9) 0.0554(8) 0.0528(8) -0.0038(6) 0.0128(7) 0.0006(6) C14 0.0630(9) 0.0649(10) 0.0600(9) -0.0076(7) 0.0034(7) 0.0046(7) C13 0.0590(9) 0.0639(10) 0.0813(12) -0.0086(8) 0.0023(8) 0.0035(7) C12 0.0556(9) 0.0655(10) 0.0877(12) -0.0011(8) 0.0233(8) 0.0009(7) C1 0.0640(9) 0.0344(7) 0.0425(7) -0.0003(5) 0.0162(6) -0.0008(6) C2 0.0603(8) 0.0484(7) 0.0345(6) -0.0013(5) 0.0093(6) -0.0007(6) C3 0.0615(8) 0.0440(7) 0.0375(7) -0.0010(5) 0.0080(6) -0.0021(6) C4 0.0699(9) 0.0421(7) 0.0373(7) -0.0014(5) 0.0063(6) -0.0019(6) C9 0.0780(10) 0.0377(7) 0.0404(7) -0.0025(5) 0.0136(7) -0.0010(6) C8 0.0964(12) 0.0536(9) 0.0411(8) -0.0040(6) 0.0182(8) -0.0021(8) C7 0.1134(14) 0.0660(10) 0.0365(8) -0.0038(7) 0.0084(8) -0.0054(9) C6 0.0958(12) 0.0700(11) 0.0437(8) -0.0017(7) -0.0058(8) -0.0048(9) C5 0.0774(10) 0.0625(9) 0.0429(8) -0.0009(6) 0.0018(7) -0.0027(7) C16 0.0541(8) 0.0607(8) 0.0320(6) 0.0034(6) 0.0005(5) -0.0004(6) C21 0.0657(9) 0.0743(10) 0.0466(8) 0.0010(7) -0.0019(6) -0.0104(8) C20 0.0554(9) 0.1006(13) 0.0567(9) 0.0154(9) -0.0032(7) -0.0169(8) C19 0.0526(9) 0.1178(15) 0.0479(8) 0.0120(9) 0.0079(7) 0.0053(9) C18 0.0633(9) 0.0908(12) 0.0449(8) -0.0041(7) 0.0076(7) 0.0099(8) C17 0.0542(8) 0.0694(10) 0.0410(7) -0.0032(6) 0.0034(6) 0.0002(7) N1 0.0704(8) 0.0435(6) 0.0425(6) -0.0013(5) 0.0166(6) 0.0004(5) O1 0.0755(8) 0.0918(9) 0.0611(7) 0.0073(6) 0.0315(6) 0.0047(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 C11 O1 1.3508(18) . ? C11 C12 1.385(2) . ? C11 C10 1.411(2) . ? C10 C15 1.395(2) . ? C10 C1 1.471(2) . ? C15 C14 1.367(2) . ? C15 H15A 0.9300 . ? C14 C13 1.376(2) . ? C14 H14A 0.9300 . ? C13 C12 1.367(2) . ? C13 H13A 0.9300 . ? C12 H12A 0.9300 . ? C1 N1 1.3286(18) . ? C1 C2 1.4167(19) . ? C2 C3 1.3581(19) . ? C2 H2A 0.9300 . ? C3 C4 1.4300(18) . ? C3 C16 1.4868(19) . ? C4 C5 1.409(2) . ? C4 C9 1.415(2) . ? C9 N1 1.3648(19) . ? C9 C8 1.4093(19) . ? C8 C7 1.350(2) . ? C8 H8A 0.9300 . ? C7 C6 1.394(3) . ? C7 H7A 0.9300 . ? C6 C5 1.368(2) . ? C6 H6A 0.9300 . ? C5 H5A 0.9300 . ? C16 C21 1.385(2) . ? C16 C17 1.3857(19) . ? C21 C20 1.381(2) . ? C21 H21A 0.9300 . ? C20 C19 1.368(2) . ? C20 H20A 0.9300 . ? C19 C18 1.364(2) . ? C19 H19A 0.9300 . ? C18 C17 1.379(2) . ? C18 H18A 0.9300 . ? C17 H17A 0.9300 . ? O1 H1 1.00(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 O1 C11 C12 118.01(13) . . ? O1 C11 C10 122.08(15) . . ? C12 C11 C10 119.91(14) . . ? C15 C10 C11 116.78(14) . . ? C15 C10 C1 121.86(12) . . ? C11 C10 C1 121.36(13) . . ? C14 C15 C10 122.69(13) . . ? C14 C15 H15A 118.7 . . ? C10 C15 H15A 118.7 . . ? C15 C14 C13 119.41(15) . . ? C15 C14 H14A 120.3 . . ? C13 C14 H14A 120.3 . . ? C12 C13 C14 119.99(16) . . ? C12 C13 H13A 120.0 . . ? C14 C13 H13A 120.0 . . ? C13 C12 C11 121.18(14) . . ? C13 C12 H12A 119.4 . . ? C11 C12 H12A 119.4 . . ? N1 C1 C2 120.39(14) . . ? N1 C1 C10 117.68(12) . . ? C2 C1 C10 121.93(12) . . ? C3 C2 C1 121.62(12) . . ? C3 C2 H2A 119.2 . . ? C1 C2 H2A 119.2 . . ? C2 C3 C4 118.58(12) . . ? C2 C3 C16 119.33(11) . . ? C4 C3 C16 122.05(12) . . ? C5 C4 C9 118.13(12) . . ? C5 C4 C3 124.72(13) . . ? C9 C4 C3 117.11(13) . . ? N1 C9 C8 118.23(14) . . ? N1 C9 C4 122.39(12) . . ? C8 C9 C4 119.37(15) . . ? C7 C8 C9 120.81(15) . . ? C7 C8 H8A 119.6 . . ? C9 C8 H8A 119.6 . . ? C8 C7 C6 120.44(14) . . ? C8 C7 H7A 119.8 . . ? C6 C7 H7A 119.8 . . ? C5 C6 C7 120.41(16) . . ? C5 C6 H6A 119.8 . . ? C7 C6 H6A 119.8 . . ? C6 C5 C4 120.83(15) . . ? C6 C5 H5A 119.6 . . ? C4 C5 H5A 119.6 . . ? C21 C16 C17 118.22(13) . . ? C21 C16 C3 122.14(12) . . ? C17 C16 C3 119.62(12) . . ? C20 C21 C16 120.61(14) . . ? C20 C21 H21A 119.7 . . ? C16 C21 H21A 119.7 . . ? C19 C20 C21 120.36(15) . . ? C19 C20 H20A 119.8 . . ? C21 C20 H20A 119.8 . . ? C18 C19 C20 119.70(14) . . ? C18 C19 H19A 120.2 . . ? C20 C19 H19A 120.2 . . ? C19 C18 C17 120.57(15) . . ? C19 C18 H18A 119.7 . . ? C17 C18 H18A 119.7 . . ? C18 C17 C16 120.54(14) . . ? C18 C17 H17A 119.7 . . ? C16 C17 H17A 119.7 . . ? C1 N1 C9 119.89(12) . . ? C11 O1 H1 104.4(12) . . ? 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 C11 C10 C15 178.28(12) . . . . ? C12 C11 C10 C15 -2.17(19) . . . . ? O1 C11 C10 C1 -1.61(19) . . . . ? C12 C11 C10 C1 177.94(12) . . . . ? C11 C10 C15 C14 0.9(2) . . . . ? C1 C10 C15 C14 -179.21(12) . . . . ? C10 C15 C14 C13 0.7(2) . . . . ? C15 C14 C13 C12 -1.0(2) . . . . ? C14 C13 C12 C11 -0.3(2) . . . . ? O1 C11 C12 C13 -178.50(13) . . . . ? C10 C11 C12 C13 1.9(2) . . . . ? C15 C10 C1 N1 -174.33(11) . . . . ? C11 C10 C1 N1 5.55(17) . . . . ? C15 C10 C1 C2 6.67(18) . . . . ? C11 C10 C1 C2 -173.44(11) . . . . ? N1 C1 C2 C3 1.07(18) . . . . ? C10 C1 C2 C3 -179.95(11) . . . . ? C1 C2 C3 C4 0.01(18) . . . . ? C1 C2 C3 C16 -177.77(11) . . . . ? C2 C3 C4 C5 -178.93(12) . . . . ? C16 C3 C4 C5 -1.2(2) . . . . ? C2 C3 C4 C9 -1.19(18) . . . . ? C16 C3 C4 C9 176.53(11) . . . . ? C5 C4 C9 N1 179.31(11) . . . . ? C3 C4 C9 N1 1.42(18) . . . . ? C5 C4 C9 C8 0.33(18) . . . . ? C3 C4 C9 C8 -177.56(11) . . . . ? N1 C9 C8 C7 -179.79(12) . . . . ? C4 C9 C8 C7 -0.8(2) . . . . ? C9 C8 C7 C6 0.1(2) . . . . ? C8 C7 C6 C5 0.9(2) . . . . ? C7 C6 C5 C4 -1.4(2) . . . . ? C9 C4 C5 C6 0.7(2) . . . . ? C3 C4 C5 C6 178.43(13) . . . . ? C2 C3 C16 C21 -125.67(14) . . . . ? C4 C3 C16 C21 56.63(18) . . . . ? C2 C3 C16 C17 52.88(17) . . . . ? C4 C3 C16 C17 -124.82(13) . . . . ? C17 C16 C21 C20 0.7(2) . . . . ? C3 C16 C21 C20 179.32(13) . . . . ? C16 C21 C20 C19 -0.2(2) . . . . ? C21 C20 C19 C18 -0.4(2) . . . . ? C20 C19 C18 C17 0.5(2) . . . . ? C19 C18 C17 C16 0.0(2) . . . . ? C21 C16 C17 C18 -0.6(2) . . . . ? C3 C16 C17 C18 -179.26(13) . . . . ? C2 C1 N1 C9 -0.87(17) . . . . ? C10 C1 N1 C9 -179.89(10) . . . . ? C8 C9 N1 C1 178.61(11) . . . . ? C4 C9 N1 C1 -0.39(18) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.195 _refine_diff_density_min -0.136 _refine_diff_density_rms 0.040