# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_p21c _database_code_depnum_ccdc_archive 'CCDC 895173' #TrackingRef '1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H22 N2 O' _chemical_formula_weight 282.38 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)/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 14.449(18) _cell_length_b 12.318(15) _cell_length_c 8.700(11) _cell_angle_alpha 90.00 _cell_angle_beta 100.103(12) _cell_angle_gamma 90.00 _cell_volume 1524(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1163 _cell_measurement_theta_min 2.86 _cell_measurement_theta_max 20.18 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.230 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9811 _exptl_absorpt_correction_T_max 0.9856 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 7898 _diffrn_reflns_av_R_equivalents 0.0494 _diffrn_reflns_av_sigmaI/netI 0.0607 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.86 _diffrn_reflns_theta_max 25.50 _reflns_number_total 2834 _reflns_number_gt 1642 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0435P)^2^+0.5290P] 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 2834 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1133 _refine_ls_R_factor_gt 0.0599 _refine_ls_wR_factor_ref 0.1386 _refine_ls_wR_factor_gt 0.1168 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _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 C1 C 1.10160(17) 0.0968(2) 0.9720(3) 0.0433(6) Uani 1 1 d . . . C2 C 1.18763(19) 0.0521(2) 0.9602(4) 0.0541(7) Uani 1 1 d . . . H2 H 1.2355 0.0464 1.0466 0.065 Uiso 1 1 calc R . . C3 C 1.1993(2) 0.0168(2) 0.8170(4) 0.0660(9) Uani 1 1 d . . . H3 H 1.2565 -0.0137 0.8048 0.079 Uiso 1 1 calc R . . C4 C 1.1281(2) 0.0254(3) 0.6889(4) 0.0672(9) Uani 1 1 d . . . H4 H 1.1384 0.0005 0.5924 0.081 Uiso 1 1 calc R . . C5 C 1.0431(2) 0.0695(2) 0.7012(3) 0.0563(8) Uani 1 1 d . . . H5 H 0.9959 0.0753 0.6139 0.068 Uiso 1 1 calc R . . C6 C 1.02797(17) 0.10571(19) 0.8456(3) 0.0422(6) Uani 1 1 d . . . C7 C 0.95082(16) 0.15406(19) 0.9041(3) 0.0415(6) Uani 1 1 d . . . C8 C 0.98178(17) 0.1701(2) 1.0590(3) 0.0459(7) Uani 1 1 d . . . H8 H 0.9458 0.2003 1.1269 0.055 Uiso 1 1 calc R . . C9 C 1.1255(2) 0.1396(2) 1.2577(3) 0.0635(8) Uani 1 1 d . . . H9A H 1.1766 0.1899 1.2613 0.095 Uiso 1 1 calc R . . H9B H 1.1501 0.0685 1.2858 0.095 Uiso 1 1 calc R . . H9C H 1.0860 0.1622 1.3297 0.095 Uiso 1 1 calc R . . C10 C 0.85764(18) 0.1767(2) 0.8168(3) 0.0455(7) Uani 1 1 d . . . C11 C 0.70323(18) 0.2559(2) 0.8152(3) 0.0561(8) Uani 1 1 d . . . H11A H 0.7052 0.2829 0.7111 0.067 Uiso 1 1 calc R . . H11B H 0.6796 0.3138 0.8733 0.067 Uiso 1 1 calc R . . C12 C 0.63661(18) 0.1620(2) 0.8031(3) 0.0610(8) Uani 1 1 d . . . H12A H 0.6622 0.1034 0.7489 0.073 Uiso 1 1 calc R . . H12B H 0.6339 0.1367 0.9078 0.073 Uiso 1 1 calc R . . C13 C 0.53874(18) 0.1840(2) 0.7216(3) 0.0510(7) Uani 1 1 d . . . C14 C 0.4775(2) 0.0882(3) 0.6864(4) 0.0730(9) Uani 1 1 d . . . H14A H 0.4617 0.0609 0.7831 0.088 Uiso 1 1 calc R . . H14B H 0.5122 0.0318 0.6433 0.088 Uiso 1 1 calc R . . C15 C 0.3878(2) 0.1104(3) 0.5734(5) 0.0951(12) Uani 1 1 d . . . H15A H 0.4014 0.1118 0.4681 0.114 Uiso 1 1 calc R . . H15B H 0.3439 0.0516 0.5793 0.114 Uiso 1 1 calc R . . C16 C 0.3439(2) 0.2120(3) 0.6039(5) 0.0977(13) Uani 1 1 d . . . H16A H 0.3234 0.2073 0.7040 0.117 Uiso 1 1 calc R . . H16B H 0.2887 0.2234 0.5244 0.117 Uiso 1 1 calc R . . C17 C 0.4079(2) 0.3066(3) 0.6055(4) 0.0796(10) Uani 1 1 d . . . H17A H 0.3838 0.3665 0.6591 0.095 Uiso 1 1 calc R . . H17B H 0.4085 0.3292 0.4989 0.095 Uiso 1 1 calc R . . C18 C 0.5056(2) 0.2825(3) 0.6833(3) 0.0674(9) Uani 1 1 d . . . H18 H 0.5466 0.3408 0.7069 0.081 Uiso 1 1 calc R . . N1 N 1.07115(14) 0.13680(17) 1.1014(2) 0.0463(6) Uani 1 1 d . . . O1 O 0.83524(12) 0.14845(15) 0.6790(2) 0.0576(5) Uani 1 1 d . . . N2 N 0.79757(14) 0.22874(18) 0.8907(3) 0.0542(6) Uani 1 1 d . . . H2A H 0.8156 0.2468 0.9867 0.065 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 0.0406(16) 0.0367(15) 0.0515(16) 0.0020(12) 0.0049(12) -0.0041(12) C2 0.0384(17) 0.0485(18) 0.072(2) 0.0030(15) 0.0013(14) -0.0005(13) C3 0.049(2) 0.061(2) 0.090(2) 0.0015(18) 0.0196(18) 0.0087(15) C4 0.064(2) 0.071(2) 0.070(2) -0.0035(17) 0.0211(18) 0.0046(17) C5 0.0526(19) 0.0598(19) 0.0550(18) -0.0024(15) 0.0058(14) 0.0004(15) C6 0.0399(16) 0.0380(15) 0.0472(15) 0.0024(12) 0.0037(12) -0.0031(12) C7 0.0388(15) 0.0385(15) 0.0446(14) 0.0019(12) 0.0002(12) -0.0039(12) C8 0.0401(16) 0.0424(16) 0.0542(16) 0.0000(13) 0.0058(12) 0.0028(12) C9 0.0584(19) 0.071(2) 0.0527(17) -0.0024(15) -0.0128(14) 0.0089(16) C10 0.0414(16) 0.0423(16) 0.0509(16) 0.0051(13) 0.0028(13) -0.0054(12) C11 0.0403(16) 0.0596(19) 0.0639(18) 0.0010(15) -0.0035(13) 0.0076(14) C12 0.0442(17) 0.064(2) 0.0720(19) 0.0126(16) 0.0022(14) 0.0062(14) C13 0.0433(16) 0.0542(18) 0.0546(16) 0.0040(14) 0.0063(13) 0.0038(14) C14 0.061(2) 0.065(2) 0.091(2) -0.0101(18) 0.0084(17) 0.0019(17) C15 0.053(2) 0.098(3) 0.126(3) -0.026(2) -0.007(2) -0.004(2) C16 0.058(2) 0.102(3) 0.121(3) -0.010(2) -0.018(2) 0.006(2) C17 0.054(2) 0.081(2) 0.095(2) 0.011(2) -0.0093(17) 0.0135(18) C18 0.0470(18) 0.064(2) 0.085(2) 0.0085(17) -0.0045(15) 0.0036(16) N1 0.0400(13) 0.0454(13) 0.0488(13) -0.0004(10) -0.0050(10) 0.0000(10) O1 0.0504(12) 0.0708(14) 0.0480(11) -0.0003(10) -0.0008(9) -0.0005(10) N2 0.0382(13) 0.0674(16) 0.0530(13) -0.0035(12) -0.0028(10) 0.0091(12) _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 N1 1.370(3) . ? C1 C2 1.380(4) . ? C1 C6 1.394(3) . ? C2 C3 1.359(4) . ? C2 H2 0.9300 . ? C3 C4 1.381(4) . ? C3 H3 0.9300 . ? C4 C5 1.365(4) . ? C4 H4 0.9300 . ? C5 C6 1.386(4) . ? C5 H5 0.9300 . ? C6 C7 1.434(4) . ? C7 C8 1.357(4) . ? C7 C10 1.452(4) . ? C8 N1 1.343(3) . ? C8 H8 0.9300 . ? C9 N1 1.447(3) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 O1 1.236(3) . ? C10 N2 1.331(3) . ? C11 N2 1.444(3) . ? C11 C12 1.496(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.491(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C18 1.325(4) . ? C13 C14 1.475(4) . ? C14 C15 1.509(4) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.448(5) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.486(5) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.485(4) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 H18 0.9300 . ? N2 H2A 0.8600 . ? 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 N1 C1 C2 128.9(2) . . ? N1 C1 C6 108.0(2) . . ? C2 C1 C6 123.1(3) . . ? C3 C2 C1 117.0(3) . . ? C3 C2 H2 121.5 . . ? C1 C2 H2 121.5 . . ? C2 C3 C4 121.4(3) . . ? C2 C3 H3 119.3 . . ? C4 C3 H3 119.3 . . ? C5 C4 C3 121.4(3) . . ? C5 C4 H4 119.3 . . ? C3 C4 H4 119.3 . . ? C4 C5 C6 119.1(3) . . ? C4 C5 H5 120.5 . . ? C6 C5 H5 120.5 . . ? C5 C6 C1 118.1(3) . . ? C5 C6 C7 135.3(2) . . ? C1 C6 C7 106.6(2) . . ? C8 C7 C6 105.7(2) . . ? C8 C7 C10 127.2(2) . . ? C6 C7 C10 127.0(2) . . ? N1 C8 C7 111.2(2) . . ? N1 C8 H8 124.4 . . ? C7 C8 H8 124.4 . . ? N1 C9 H9A 109.5 . . ? N1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O1 C10 N2 121.5(2) . . ? O1 C10 C7 121.0(2) . . ? N2 C10 C7 117.6(2) . . ? N2 C11 C12 113.4(2) . . ? N2 C11 H11A 108.9 . . ? C12 C11 H11A 108.9 . . ? N2 C11 H11B 108.9 . . ? C12 C11 H11B 108.9 . . ? H11A C11 H11B 107.7 . . ? C13 C12 C11 116.0(2) . . ? C13 C12 H12A 108.3 . . ? C11 C12 H12A 108.3 . . ? C13 C12 H12B 108.3 . . ? C11 C12 H12B 108.3 . . ? H12A C12 H12B 107.4 . . ? C18 C13 C14 120.2(3) . . ? C18 C13 C12 123.8(3) . . ? C14 C13 C12 116.0(3) . . ? C13 C14 C15 114.0(3) . . ? C13 C14 H14A 108.8 . . ? C15 C14 H14A 108.8 . . ? C13 C14 H14B 108.8 . . ? C15 C14 H14B 108.8 . . ? H14A C14 H14B 107.7 . . ? C16 C15 C14 113.0(3) . . ? C16 C15 H15A 109.0 . . ? C14 C15 H15A 109.0 . . ? C16 C15 H15B 109.0 . . ? C14 C15 H15B 109.0 . . ? H15A C15 H15B 107.8 . . ? C15 C16 C17 112.8(3) . . ? C15 C16 H16A 109.0 . . ? C17 C16 H16A 109.0 . . ? C15 C16 H16B 109.0 . . ? C17 C16 H16B 109.0 . . ? H16A C16 H16B 107.8 . . ? C16 C17 C18 112.8(3) . . ? C16 C17 H17A 109.0 . . ? C18 C17 H17A 109.0 . . ? C16 C17 H17B 109.0 . . ? C18 C17 H17B 109.0 . . ? H17A C17 H17B 107.8 . . ? C13 C18 C17 124.7(3) . . ? C13 C18 H18 117.6 . . ? C17 C18 H18 117.6 . . ? C8 N1 C1 108.4(2) . . ? C8 N1 C9 126.1(2) . . ? C1 N1 C9 125.5(2) . . ? C10 N2 C11 122.3(2) . . ? C10 N2 H2A 118.8 . . ? C11 N2 H2A 118.8 . . ? 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 N1 C1 C2 C3 179.0(3) . . . . ? C6 C1 C2 C3 0.7(4) . . . . ? C1 C2 C3 C4 0.0(4) . . . . ? C2 C3 C4 C5 -0.1(5) . . . . ? C3 C4 C5 C6 -0.5(4) . . . . ? C4 C5 C6 C1 1.1(4) . . . . ? C4 C5 C6 C7 -179.3(3) . . . . ? N1 C1 C6 C5 -179.8(2) . . . . ? C2 C1 C6 C5 -1.2(4) . . . . ? N1 C1 C6 C7 0.4(3) . . . . ? C2 C1 C6 C7 179.1(2) . . . . ? C5 C6 C7 C8 179.8(3) . . . . ? C1 C6 C7 C8 -0.5(3) . . . . ? C5 C6 C7 C10 2.2(5) . . . . ? C1 C6 C7 C10 -178.1(2) . . . . ? C6 C7 C8 N1 0.4(3) . . . . ? C10 C7 C8 N1 178.0(2) . . . . ? C8 C7 C10 O1 -172.7(2) . . . . ? C6 C7 C10 O1 4.4(4) . . . . ? C8 C7 C10 N2 7.2(4) . . . . ? C6 C7 C10 N2 -175.7(2) . . . . ? N2 C11 C12 C13 -178.1(2) . . . . ? C11 C12 C13 C18 -10.9(4) . . . . ? C11 C12 C13 C14 170.2(3) . . . . ? C18 C13 C14 C15 14.1(4) . . . . ? C12 C13 C14 C15 -166.8(3) . . . . ? C13 C14 C15 C16 -42.2(5) . . . . ? C14 C15 C16 C17 55.7(5) . . . . ? C15 C16 C17 C18 -40.0(5) . . . . ? C14 C13 C18 C17 0.4(5) . . . . ? C12 C13 C18 C17 -178.5(3) . . . . ? C16 C17 C18 C13 12.2(5) . . . . ? C7 C8 N1 C1 -0.1(3) . . . . ? C7 C8 N1 C9 -178.5(2) . . . . ? C2 C1 N1 C8 -178.7(3) . . . . ? C6 C1 N1 C8 -0.2(3) . . . . ? C2 C1 N1 C9 -0.3(4) . . . . ? C6 C1 N1 C9 178.2(2) . . . . ? O1 C10 N2 C11 -0.3(4) . . . . ? C7 C10 N2 C11 179.8(2) . . . . ? C12 C11 N2 C10 78.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.268 _refine_diff_density_min -0.193 _refine_diff_density_rms 0.038 data_p21ca _database_code_depnum_ccdc_archive 'CCDC 895174' #TrackingRef '2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H15 N2 O2' _chemical_formula_weight 291.32 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)/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 8.604(3) _cell_length_b 17.584(7) _cell_length_c 10.173(4) _cell_angle_alpha 90.00 _cell_angle_beta 97.577(4) _cell_angle_gamma 90.00 _cell_volume 1525.7(10) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2303 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 28.21 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.268 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 612 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9809 _exptl_absorpt_correction_T_max 0.9867 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 7216 _diffrn_reflns_av_R_equivalents 0.0337 _diffrn_reflns_av_sigmaI/netI 0.0480 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 25.50 _reflns_number_total 2810 _reflns_number_gt 1700 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0734P)^2^+0.0791P] 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 2810 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1021 _refine_ls_R_factor_gt 0.0569 _refine_ls_wR_factor_ref 0.1587 _refine_ls_wR_factor_gt 0.1367 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _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 C1 C 0.3872(3) 0.56231(13) 0.8437(2) 0.0466(6) Uani 1 1 d . . . C2 C 0.3009(3) 0.50281(14) 0.8986(2) 0.0461(6) Uani 1 1 d . . . C3 C 0.2452(3) 0.43096(14) 0.8566(3) 0.0571(7) Uani 1 1 d . . . H3 H 0.2636 0.4118 0.7748 0.069 Uiso 1 1 calc R . . C4 C 0.1629(3) 0.38918(16) 0.9380(3) 0.0645(8) Uani 1 1 d . . . H4 H 0.1261 0.3412 0.9105 0.077 Uiso 1 1 calc R . . C5 C 0.1328(3) 0.41661(17) 1.0607(3) 0.0646(8) Uani 1 1 d . . . H5 H 0.0776 0.3866 1.1139 0.077 Uiso 1 1 calc R . . C6 C 0.1835(3) 0.48737(16) 1.1041(3) 0.0590(7) Uani 1 1 d . . . H6 H 0.1624 0.5065 1.1851 0.071 Uiso 1 1 calc R . . C7 C 0.2673(3) 0.52890(14) 1.0220(2) 0.0494(6) Uani 1 1 d . . . C8 C 0.4018(3) 0.62068(14) 0.9357(2) 0.0537(7) Uani 1 1 d . . . H8 H 0.4530 0.6665 0.9259 0.064 Uiso 1 1 calc R . . C9 C 0.4512(3) 0.55896(14) 0.7208(3) 0.0497(6) Uani 1 1 d . . . C10 C 0.5302(3) 0.62970(15) 0.6692(3) 0.0517(7) Uani 1 1 d . . . C11 C 0.6515(3) 0.67834(15) 0.4834(3) 0.0595(7) Uani 1 1 d . . . H11A H 0.6335 0.7263 0.5261 0.071 Uiso 1 1 calc R . . H11B H 0.5993 0.6810 0.3930 0.071 Uiso 1 1 calc R . . C12 C 0.8246(3) 0.66962(15) 0.4797(2) 0.0540(7) Uani 1 1 d . . . C13 C 0.8962(3) 0.71537(16) 0.3953(3) 0.0684(8) Uani 1 1 d . . . H13 H 0.8360 0.7492 0.3396 0.082 Uiso 1 1 calc R . . C14 C 1.0556(4) 0.7117(2) 0.3923(4) 0.0953(11) Uani 1 1 d . . . H14 H 1.1028 0.7437 0.3364 0.114 Uiso 1 1 calc R . . C15 C 1.1433(4) 0.6615(3) 0.4708(4) 0.1306(17) Uani 1 1 d . . . H15 H 1.2508 0.6585 0.4687 0.157 Uiso 1 1 calc R . . C16 C 1.0729(5) 0.6152(4) 0.5535(4) 0.162(2) Uani 1 1 d . . . H16 H 1.1332 0.5805 0.6072 0.195 Uiso 1 1 calc R . . C17 C 0.9141(4) 0.6193(2) 0.5582(3) 0.1033(13) Uani 1 1 d . . . H17 H 0.8679 0.5876 0.6151 0.124 Uiso 1 1 calc R . . C18 C 0.3240(4) 0.64783(17) 1.1597(3) 0.0818(10) Uani 1 1 d . . . H18A H 0.3813 0.6942 1.1527 0.123 Uiso 1 1 calc R . . H18B H 0.3693 0.6202 1.2366 0.123 Uiso 1 1 calc R . . H18C H 0.2166 0.6596 1.1674 0.123 Uiso 1 1 calc R . . N1 N 0.3312(2) 0.60158(12) 1.0413(2) 0.0558(6) Uani 1 1 d . . . N2 N 0.5798(2) 0.61818(12) 0.5517(2) 0.0556(6) Uani 1 1 d . . . O1 O 0.4432(2) 0.50143(10) 0.65099(17) 0.0664(6) Uani 1 1 d . . . O2 O 0.5411(2) 0.69032(10) 0.72980(18) 0.0748(6) Uani 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 C1 0.0471(14) 0.0495(15) 0.0427(14) -0.0025(12) 0.0036(11) 0.0060(11) C2 0.0466(13) 0.0477(15) 0.0425(14) 0.0012(12) 0.0009(10) 0.0060(12) C3 0.0661(17) 0.0562(17) 0.0488(15) -0.0034(13) 0.0067(13) 0.0001(14) C4 0.0753(19) 0.0555(17) 0.0626(19) 0.0026(15) 0.0091(15) -0.0075(14) C5 0.0660(18) 0.0649(19) 0.0637(19) 0.0153(15) 0.0122(14) 0.0015(15) C6 0.0627(16) 0.0665(19) 0.0485(15) 0.0035(14) 0.0101(13) 0.0102(14) C7 0.0490(14) 0.0507(16) 0.0471(15) 0.0013(12) 0.0012(11) 0.0098(12) C8 0.0561(15) 0.0534(16) 0.0512(16) 0.0004(13) 0.0060(12) 0.0001(13) C9 0.0495(14) 0.0474(15) 0.0512(16) -0.0026(13) 0.0026(12) 0.0011(12) C10 0.0515(15) 0.0495(16) 0.0524(16) 0.0010(13) 0.0002(12) 0.0011(12) C11 0.0597(16) 0.0612(17) 0.0581(16) 0.0076(14) 0.0101(13) 0.0022(13) C12 0.0528(15) 0.0664(18) 0.0429(14) -0.0099(13) 0.0065(12) -0.0026(13) C13 0.0696(19) 0.0647(18) 0.075(2) -0.0108(16) 0.0232(15) -0.0058(15) C14 0.077(2) 0.123(3) 0.092(3) -0.025(2) 0.033(2) -0.021(2) C15 0.050(2) 0.247(6) 0.095(3) -0.004(3) 0.012(2) 0.008(3) C16 0.074(3) 0.306(7) 0.104(3) 0.068(4) 0.000(2) 0.047(4) C17 0.059(2) 0.172(4) 0.078(2) 0.040(2) 0.0072(17) 0.025(2) C18 0.118(3) 0.073(2) 0.0574(18) -0.0233(16) 0.0219(17) -0.0012(18) N1 0.0649(14) 0.0542(14) 0.0484(13) -0.0072(11) 0.0079(11) 0.0048(11) N2 0.0591(13) 0.0594(14) 0.0504(13) 0.0036(11) 0.0157(10) -0.0015(10) O1 0.0899(14) 0.0553(11) 0.0575(11) -0.0137(10) 0.0233(10) -0.0093(10) O2 0.1099(17) 0.0517(12) 0.0662(13) -0.0125(10) 0.0237(11) -0.0118(11) _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 C8 1.383(3) . ? C1 C9 1.433(3) . ? C1 C2 1.438(3) . ? C2 C3 1.398(3) . ? C2 C7 1.402(3) . ? C3 C4 1.372(3) . ? C3 H3 0.9300 . ? C4 C5 1.394(4) . ? C4 H4 0.9300 . ? C5 C6 1.372(4) . ? C5 H5 0.9300 . ? C6 C7 1.381(4) . ? C6 H6 0.9300 . ? C7 N1 1.395(3) . ? C8 N1 1.345(3) . ? C8 H8 0.9300 . ? C9 O1 1.233(3) . ? C9 C10 1.542(3) . ? C10 O2 1.229(3) . ? C10 N2 1.337(3) . ? C11 N2 1.448(3) . ? C11 C12 1.502(3) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C17 1.361(4) . ? C12 C13 1.380(4) . ? C13 C14 1.378(4) . ? C13 H13 0.9300 . ? C14 C15 1.351(5) . ? C14 H14 0.9300 . ? C15 C16 1.369(6) . ? C15 H15 0.9300 . ? C16 C17 1.375(5) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 N1 1.461(3) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 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 C8 C1 C9 127.6(2) . . ? C8 C1 C2 106.4(2) . . ? C9 C1 C2 125.9(2) . . ? C3 C2 C7 117.8(2) . . ? C3 C2 C1 135.4(2) . . ? C7 C2 C1 106.7(2) . . ? C4 C3 C2 118.9(2) . . ? C4 C3 H3 120.6 . . ? C2 C3 H3 120.6 . . ? C3 C4 C5 121.8(3) . . ? C3 C4 H4 119.1 . . ? C5 C4 H4 119.1 . . ? C6 C5 C4 120.9(3) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C5 C6 C7 117.0(3) . . ? C5 C6 H6 121.5 . . ? C7 C6 H6 121.5 . . ? C6 C7 N1 128.8(2) . . ? C6 C7 C2 123.6(2) . . ? N1 C7 C2 107.6(2) . . ? N1 C8 C1 110.2(2) . . ? N1 C8 H8 124.9 . . ? C1 C8 H8 124.9 . . ? O1 C9 C1 122.5(2) . . ? O1 C9 C10 117.4(2) . . ? C1 C9 C10 120.1(2) . . ? O2 C10 N2 124.6(2) . . ? O2 C10 C9 122.5(2) . . ? N2 C10 C9 112.9(2) . . ? N2 C11 C12 115.1(2) . . ? N2 C11 H11A 108.5 . . ? C12 C11 H11A 108.5 . . ? N2 C11 H11B 108.5 . . ? C12 C11 H11B 108.5 . . ? H11A C11 H11B 107.5 . . ? C17 C12 C13 118.6(3) . . ? C17 C12 C11 122.5(3) . . ? C13 C12 C11 118.8(2) . . ? C12 C13 C14 121.0(3) . . ? C12 C13 H13 119.5 . . ? C14 C13 H13 119.5 . . ? C15 C14 C13 119.8(4) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C14 C15 C16 119.7(4) . . ? C14 C15 H15 120.2 . . ? C16 C15 H15 120.2 . . ? C15 C16 C17 120.8(4) . . ? C15 C16 H16 119.6 . . ? C17 C16 H16 119.6 . . ? C12 C17 C16 120.2(4) . . ? C12 C17 H17 119.9 . . ? C16 C17 H17 119.9 . . ? N1 C18 H18A 109.5 . . ? N1 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N1 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C8 N1 C7 109.1(2) . . ? C8 N1 C18 126.3(2) . . ? C7 N1 C18 124.6(2) . . ? C10 N2 C11 121.7(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 C8 C1 C2 C3 178.6(3) . . . . ? C9 C1 C2 C3 -4.3(4) . . . . ? C8 C1 C2 C7 0.2(2) . . . . ? C9 C1 C2 C7 177.3(2) . . . . ? C7 C2 C3 C4 -0.9(3) . . . . ? C1 C2 C3 C4 -179.2(2) . . . . ? C2 C3 C4 C5 0.4(4) . . . . ? C3 C4 C5 C6 0.7(4) . . . . ? C4 C5 C6 C7 -1.1(4) . . . . ? C5 C6 C7 N1 179.7(2) . . . . ? C5 C6 C7 C2 0.6(3) . . . . ? C3 C2 C7 C6 0.5(3) . . . . ? C1 C2 C7 C6 179.2(2) . . . . ? C3 C2 C7 N1 -178.8(2) . . . . ? C1 C2 C7 N1 -0.1(2) . . . . ? C9 C1 C8 N1 -177.3(2) . . . . ? C2 C1 C8 N1 -0.2(3) . . . . ? C8 C1 C9 O1 173.4(2) . . . . ? C2 C1 C9 O1 -3.1(4) . . . . ? C8 C1 C9 C10 -8.2(4) . . . . ? C2 C1 C9 C10 175.2(2) . . . . ? O1 C9 C10 O2 178.4(2) . . . . ? C1 C9 C10 O2 0.0(3) . . . . ? O1 C9 C10 N2 0.3(3) . . . . ? C1 C9 C10 N2 -178.2(2) . . . . ? N2 C11 C12 C17 -14.0(4) . . . . ? N2 C11 C12 C13 167.3(2) . . . . ? C17 C12 C13 C14 -1.5(4) . . . . ? C11 C12 C13 C14 177.3(3) . . . . ? C12 C13 C14 C15 1.5(5) . . . . ? C13 C14 C15 C16 -0.5(7) . . . . ? C14 C15 C16 C17 -0.3(8) . . . . ? C13 C12 C17 C16 0.6(5) . . . . ? C11 C12 C17 C16 -178.1(4) . . . . ? C15 C16 C17 C12 0.3(8) . . . . ? C1 C8 N1 C7 0.1(3) . . . . ? C1 C8 N1 C18 178.9(2) . . . . ? C6 C7 N1 C8 -179.2(2) . . . . ? C2 C7 N1 C8 0.0(3) . . . . ? C6 C7 N1 C18 1.9(4) . . . . ? C2 C7 N1 C18 -178.8(2) . . . . ? O2 C10 N2 C11 -0.6(4) . . . . ? C9 C10 N2 C11 177.5(2) . . . . ? C12 C11 N2 C10 108.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.380 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.040