# 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_120508c _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H18 N2 O2' _chemical_formula_weight 378.41 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 13.5501(17) _cell_length_b 13.4406(17) _cell_length_c 10.7332(13) _cell_angle_alpha 90.00 _cell_angle_beta 98.124(2) _cell_angle_gamma 90.00 _cell_volume 1935.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1325 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 19.94 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.299 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9917 _exptl_absorpt_correction_T_max 0.9975 _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 9883 _diffrn_reflns_av_R_equivalents 0.0412 _diffrn_reflns_av_sigmaI/netI 0.0461 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 25.05 _reflns_number_total 3420 _reflns_number_gt 2173 _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^)+(0.0559P)^2^+0.4760P] 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 SHELXL _refine_ls_extinction_coef 0.0058(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3420 _refine_ls_number_parameters 265 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0988 _refine_ls_R_factor_gt 0.0606 _refine_ls_wR_factor_ref 0.1655 _refine_ls_wR_factor_gt 0.1349 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _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 0.2349(2) 0.60270(19) 0.4114(3) 0.0574(7) Uani 1 1 d . . . C2 C 0.1711(2) 0.6624(2) 0.4695(3) 0.0700(9) Uani 1 1 d . . . C3 C 0.1698(3) 0.7633(3) 0.4438(4) 0.0911(12) Uani 1 1 d . . . H3 H 0.1288 0.8054 0.4824 0.109 Uiso 1 1 calc R . . C4 C 0.2287(3) 0.8014(3) 0.3618(4) 0.0951(13) Uani 1 1 d . . . H4 H 0.2276 0.8694 0.3457 0.114 Uiso 1 1 calc R . . C5 C 0.2898(3) 0.7407(2) 0.3025(3) 0.0835(11) Uani 1 1 d . . . H5 H 0.3275 0.7679 0.2449 0.100 Uiso 1 1 calc R . . C6 C 0.2955(2) 0.6393(2) 0.3283(3) 0.0653(8) Uani 1 1 d . . . C7 C 0.3642(3) 0.5729(3) 0.2682(4) 0.0951(12) Uani 1 1 d . . . H7A H 0.4172 0.5505 0.3308 0.143 Uiso 1 1 calc R . . H7B H 0.3918 0.6093 0.2042 0.143 Uiso 1 1 calc R . . H7C H 0.3278 0.5166 0.2310 0.143 Uiso 1 1 calc R . . C8 C 0.1041(3) 0.6196(3) 0.5559(4) 0.0977(12) Uani 1 1 d . . . H8A H 0.0762 0.6725 0.5999 0.147 Uiso 1 1 calc R . . H8B H 0.1419 0.5761 0.6156 0.147 Uiso 1 1 calc R . . H8C H 0.0513 0.5827 0.5076 0.147 Uiso 1 1 calc R . . C9 C 0.2961(2) 0.4573(2) 0.5468(3) 0.0602(8) Uani 1 1 d . . . C10 C 0.1702(2) 0.42858(19) 0.3814(3) 0.0534(7) Uani 1 1 d . . . C11 C 0.26119(19) 0.35271(19) 0.5556(3) 0.0516(7) Uani 1 1 d . . . C12 C 0.2907(2) 0.2748(2) 0.6433(3) 0.0549(7) Uani 1 1 d . . . C13 C 0.1843(2) 0.16633(19) 0.5189(3) 0.0548(7) Uani 1 1 d . . . C14 C 0.1466(2) 0.0685(2) 0.5001(3) 0.0696(9) Uani 1 1 d . . . H14 H 0.1675 0.0191 0.5585 0.084 Uiso 1 1 calc R . . C15 C 0.0800(2) 0.0465(2) 0.3970(3) 0.0731(9) Uani 1 1 d . . . H15 H 0.0559 -0.0182 0.3856 0.088 Uiso 1 1 calc R . . C16 C 0.0472(2) 0.1193(2) 0.3079(3) 0.0734(9) Uani 1 1 d . . . H16 H 0.0016 0.1024 0.2380 0.088 Uiso 1 1 calc R . . C17 C 0.0807(2) 0.2146(2) 0.3216(3) 0.0652(8) Uani 1 1 d . . . H17 H 0.0585 0.2626 0.2617 0.078 Uiso 1 1 calc R . . C18 C 0.1498(2) 0.23955(19) 0.4283(3) 0.0531(7) Uani 1 1 d . . . C19 C 0.19186(19) 0.33442(19) 0.4533(2) 0.0506(7) Uani 1 1 d . . . C20 C 0.3618(2) 0.2885(2) 0.7606(3) 0.0558(7) Uani 1 1 d . . . C21 C 0.3602(2) 0.3733(2) 0.8339(3) 0.0663(8) Uani 1 1 d . . . H21 H 0.3157 0.4244 0.8079 0.080 Uiso 1 1 calc R . . C22 C 0.4246(3) 0.3821(3) 0.9454(3) 0.0795(10) Uani 1 1 d . . . H22 H 0.4227 0.4387 0.9950 0.095 Uiso 1 1 calc R . . C23 C 0.4912(3) 0.3075(3) 0.9830(3) 0.0908(12) Uani 1 1 d . . . H23 H 0.5356 0.3146 1.0569 0.109 Uiso 1 1 calc R . . C24 C 0.4929(3) 0.2228(3) 0.9130(3) 0.0824(10) Uani 1 1 d . . . H24 H 0.5376 0.1721 0.9400 0.099 Uiso 1 1 calc R . . C25 C 0.4282(2) 0.2127(2) 0.8021(3) 0.0696(9) Uani 1 1 d . . . H25 H 0.4292 0.1548 0.7548 0.084 Uiso 1 1 calc R . . N1 N 0.23745(17) 0.49774(15) 0.4408(2) 0.0564(6) Uani 1 1 d . . . N2 N 0.25215(17) 0.18504(16) 0.6239(2) 0.0588(6) Uani 1 1 d . . . O1 O 0.35947(18) 0.50395(15) 0.6122(2) 0.0844(8) Uani 1 1 d . . . O2 O 0.10748(15) 0.44569(14) 0.29357(19) 0.0692(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 0.0606(18) 0.0466(15) 0.0625(18) 0.0031(13) -0.0002(14) -0.0004(13) C2 0.073(2) 0.0627(19) 0.072(2) -0.0031(16) 0.0023(17) 0.0038(16) C3 0.107(3) 0.059(2) 0.106(3) -0.003(2) 0.009(2) 0.016(2) C4 0.120(3) 0.051(2) 0.105(3) 0.009(2) -0.017(3) 0.002(2) C5 0.099(3) 0.066(2) 0.082(2) 0.0139(19) -0.002(2) -0.016(2) C6 0.069(2) 0.0598(18) 0.066(2) 0.0017(15) 0.0057(16) -0.0056(15) C7 0.096(3) 0.089(3) 0.108(3) -0.001(2) 0.041(2) -0.011(2) C8 0.098(3) 0.102(3) 0.101(3) -0.013(2) 0.038(2) -0.002(2) C9 0.0590(18) 0.0558(17) 0.0630(18) 0.0056(14) -0.0013(15) -0.0055(14) C10 0.0526(17) 0.0503(16) 0.0559(17) -0.0011(13) 0.0022(14) -0.0006(13) C11 0.0491(16) 0.0484(15) 0.0570(17) 0.0008(12) 0.0061(13) -0.0029(12) C12 0.0496(16) 0.0536(16) 0.0616(18) 0.0052(14) 0.0079(13) -0.0022(13) C13 0.0537(17) 0.0497(16) 0.0615(18) 0.0008(14) 0.0103(14) -0.0017(13) C14 0.076(2) 0.0537(17) 0.079(2) 0.0013(16) 0.0099(17) -0.0103(15) C15 0.076(2) 0.0560(18) 0.086(2) -0.0093(17) 0.0063(18) -0.0149(16) C16 0.071(2) 0.0647(19) 0.082(2) -0.0147(18) 0.0003(17) -0.0089(17) C17 0.0619(19) 0.0605(18) 0.070(2) -0.0044(15) -0.0001(15) -0.0032(15) C18 0.0470(16) 0.0499(15) 0.0631(17) -0.0072(13) 0.0103(13) -0.0008(12) C19 0.0465(16) 0.0463(15) 0.0582(17) 0.0003(12) 0.0055(13) 0.0034(12) C20 0.0504(17) 0.0629(18) 0.0538(17) 0.0102(14) 0.0065(13) -0.0059(14) C21 0.065(2) 0.070(2) 0.0624(19) 0.0034(16) 0.0051(15) -0.0074(15) C22 0.079(2) 0.099(3) 0.061(2) -0.0047(18) 0.0097(18) -0.020(2) C23 0.070(2) 0.135(4) 0.064(2) 0.014(2) -0.0028(18) -0.012(2) C24 0.067(2) 0.109(3) 0.069(2) 0.028(2) 0.0018(18) 0.005(2) C25 0.069(2) 0.074(2) 0.065(2) 0.0166(16) 0.0071(16) 0.0035(16) N1 0.0586(15) 0.0459(13) 0.0620(15) 0.0075(11) -0.0004(12) 0.0006(11) N2 0.0584(15) 0.0520(14) 0.0653(15) 0.0043(12) 0.0063(12) -0.0048(11) O1 0.0901(16) 0.0677(14) 0.0854(16) 0.0137(12) -0.0223(13) -0.0271(12) O2 0.0734(14) 0.0610(13) 0.0678(13) 0.0018(10) -0.0093(11) 0.0071(10) _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 C6 1.385(4) . ? C1 C2 1.390(4) . ? C1 N1 1.445(3) . ? C2 C3 1.383(5) . ? C2 C8 1.502(5) . ? C3 C4 1.368(5) . ? C3 H3 0.9300 . ? C4 C5 1.380(5) . ? C4 H4 0.9300 . ? C5 C6 1.391(4) . ? C5 H5 0.9300 . ? C6 C7 1.500(4) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 O1 1.205(3) . ? C9 N1 1.402(3) . ? C9 C11 1.491(4) . ? C10 O2 1.199(3) . ? C10 N1 1.392(3) . ? C10 C19 1.489(4) . ? C11 C19 1.363(3) . ? C11 C12 1.428(4) . ? C12 N2 1.319(3) . ? C12 C20 1.485(4) . ? C13 N2 1.373(3) . ? C13 C14 1.415(4) . ? C13 C18 1.415(4) . ? C14 C15 1.358(4) . ? C14 H14 0.9300 . ? C15 C16 1.397(4) . ? C15 H15 0.9300 . ? C16 C17 1.360(4) . ? C16 H16 0.9300 . ? C17 C18 1.414(4) . ? C17 H17 0.9300 . ? C18 C19 1.407(3) . ? C20 C21 1.386(4) . ? C20 C25 1.391(4) . ? C21 C22 1.383(4) . ? C21 H21 0.9300 . ? C22 C23 1.372(5) . ? C22 H22 0.9300 . ? C23 C24 1.365(5) . ? C23 H23 0.9300 . ? C24 C25 1.382(4) . ? C24 H24 0.9300 . ? C25 H25 0.9300 . ? 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 C6 C1 C2 123.1(3) . . ? C6 C1 N1 119.3(3) . . ? C2 C1 N1 117.6(3) . . ? C3 C2 C1 117.9(3) . . ? C3 C2 C8 120.5(3) . . ? C1 C2 C8 121.6(3) . . ? C4 C3 C2 120.1(4) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C3 C4 C5 121.3(3) . . ? C3 C4 H4 119.4 . . ? C5 C4 H4 119.4 . . ? C4 C5 C6 120.4(4) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C1 C6 C5 117.1(3) . . ? C1 C6 C7 121.8(3) . . ? C5 C6 C7 121.1(3) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C2 C8 H8A 109.5 . . ? C2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O1 C9 N1 123.1(3) . . ? O1 C9 C11 131.3(3) . . ? N1 C9 C11 105.5(2) . . ? O2 C10 N1 125.3(2) . . ? O2 C10 C19 129.5(2) . . ? N1 C10 C19 105.2(2) . . ? C19 C11 C12 119.7(2) . . ? C19 C11 C9 108.0(2) . . ? C12 C11 C9 132.2(2) . . ? N2 C12 C11 119.9(2) . . ? N2 C12 C20 116.3(2) . . ? C11 C12 C20 123.8(2) . . ? N2 C13 C14 118.3(3) . . ? N2 C13 C18 123.6(2) . . ? C14 C13 C18 118.1(3) . . ? C15 C14 C13 120.3(3) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C14 C15 C16 121.1(3) . . ? C14 C15 H15 119.5 . . ? C16 C15 H15 119.5 . . ? C17 C16 C15 121.1(3) . . ? C17 C16 H16 119.5 . . ? C15 C16 H16 119.5 . . ? C16 C17 C18 118.9(3) . . ? C16 C17 H17 120.5 . . ? C18 C17 H17 120.5 . . ? C19 C18 C17 124.9(3) . . ? C19 C18 C13 114.5(2) . . ? C17 C18 C13 120.6(2) . . ? C11 C19 C18 122.1(2) . . ? C11 C19 C10 109.1(2) . . ? C18 C19 C10 128.8(2) . . ? C21 C20 C25 118.8(3) . . ? C21 C20 C12 121.6(3) . . ? C25 C20 C12 119.6(3) . . ? C22 C21 C20 120.3(3) . . ? C22 C21 H21 119.9 . . ? C20 C21 H21 119.9 . . ? C23 C22 C21 120.0(4) . . ? C23 C22 H22 120.0 . . ? C21 C22 H22 120.0 . . ? C24 C23 C22 120.6(3) . . ? C24 C23 H23 119.7 . . ? C22 C23 H23 119.7 . . ? C23 C24 C25 119.9(3) . . ? C23 C24 H24 120.1 . . ? C25 C24 H24 120.1 . . ? C24 C25 C20 120.4(3) . . ? C24 C25 H25 119.8 . . ? C20 C25 H25 119.8 . . ? C10 N1 C9 111.9(2) . . ? C10 N1 C1 123.9(2) . . ? C9 N1 C1 123.3(2) . . ? C12 N2 C13 120.1(2) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.203 _refine_diff_density_min -0.151 _refine_diff_density_rms 0.040 _database_code_depnum_ccdc_archive 'CCDC 945280' ####################################################################### # # 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_121203a_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H20 N2 O3' _chemical_formula_weight 408.44 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 8.5140(9) _cell_length_b 13.6267(14) _cell_length_c 18.6805(19) _cell_angle_alpha 90.00 _cell_angle_beta 100.8290(10) _cell_angle_gamma 90.00 _cell_volume 2128.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3468 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 25.43 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.274 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9801 _exptl_absorpt_correction_T_max 0.9900 _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 10805 _diffrn_reflns_av_R_equivalents 0.0180 _diffrn_reflns_av_sigmaI/netI 0.0200 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 25.05 _reflns_number_total 3761 _reflns_number_gt 2855 _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^)+(0.0520P)^2^+0.3612P] 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 SHELXL _refine_ls_extinction_coef 0.0045(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3761 _refine_ls_number_parameters 284 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0546 _refine_ls_R_factor_gt 0.0399 _refine_ls_wR_factor_ref 0.1102 _refine_ls_wR_factor_gt 0.1002 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 0.2803(2) 0.00081(12) 0.52293(9) 0.0540(4) Uani 1 1 d . . . C2 C 0.2791(3) -0.10329(13) 0.51998(11) 0.0705(6) Uani 1 1 d . . . H2 H 0.3415 -0.1390 0.5573 0.085 Uiso 1 1 calc R . . C3 C 0.1883(3) -0.15114(14) 0.46349(10) 0.0725(6) Uani 1 1 d . . . H3 H 0.1896 -0.2194 0.4625 0.087 Uiso 1 1 calc R . . C4 C 0.0915(2) -0.09952(13) 0.40589(9) 0.0596(5) Uani 1 1 d . . . C5 C 0.0926(2) 0.00066(12) 0.40485(9) 0.0525(4) Uani 1 1 d . . . H5 H 0.0316 0.0348 0.3663 0.063 Uiso 1 1 calc R . . C6 C 0.1875(2) 0.05180(11) 0.46302(9) 0.0479(4) Uani 1 1 d . . . C7 C 0.20085(18) 0.15406(11) 0.46776(8) 0.0451(4) Uani 1 1 d . . . C8 C 0.13353(19) 0.23007(11) 0.41301(9) 0.0471(4) Uani 1 1 d . . . C9 C 0.28584(19) 0.30759(12) 0.51273(9) 0.0467(4) Uani 1 1 d . . . C10 C 0.28864(19) 0.19980(12) 0.52761(8) 0.0464(4) Uani 1 1 d . . . C11 C 0.36903(19) 0.14334(13) 0.58725(8) 0.0501(4) Uani 1 1 d . . . C12 C 0.4579(2) 0.18780(14) 0.65563(8) 0.0531(4) Uani 1 1 d . . . C13 C 0.3967(2) 0.26664(14) 0.68792(9) 0.0622(5) Uani 1 1 d . . . H13 H 0.2967 0.2917 0.6674 0.075 Uiso 1 1 calc R . . C14 C 0.4835(3) 0.30866(17) 0.75082(10) 0.0753(6) Uani 1 1 d . . . H14 H 0.4413 0.3613 0.7726 0.090 Uiso 1 1 calc R . . C15 C 0.6313(3) 0.2726(2) 0.78073(11) 0.0839(7) Uani 1 1 d . . . H15 H 0.6912 0.3023 0.8218 0.101 Uiso 1 1 calc R . . C16 C 0.6906(3) 0.1931(2) 0.75037(11) 0.0875(7) Uani 1 1 d . . . H16 H 0.7899 0.1678 0.7716 0.105 Uiso 1 1 calc R . . C17 C 0.6047(2) 0.14995(17) 0.68843(9) 0.0695(6) Uani 1 1 d . . . H17 H 0.6456 0.0951 0.6686 0.083 Uiso 1 1 calc R . . C18 C -0.0842(3) -0.10905(15) 0.29085(11) 0.0754(6) Uani 1 1 d . . . H18A H -0.1668 -0.0695 0.3047 0.113 Uiso 1 1 calc R . . H18B H -0.1315 -0.1573 0.2559 0.113 Uiso 1 1 calc R . . H18C H -0.0134 -0.0681 0.2697 0.113 Uiso 1 1 calc R . . C19 C 0.14718(18) 0.41311(11) 0.40954(8) 0.0433(4) Uani 1 1 d . . . C20 C -0.00818(19) 0.44739(11) 0.40565(8) 0.0464(4) Uani 1 1 d . . . C21 C -0.0474(2) 0.53606(13) 0.37063(10) 0.0619(5) Uani 1 1 d . . . H21 H -0.1514 0.5597 0.3653 0.074 Uiso 1 1 calc R . . C22 C 0.0649(3) 0.58949(14) 0.34366(11) 0.0747(6) Uani 1 1 d . . . H22 H 0.0369 0.6494 0.3210 0.090 Uiso 1 1 calc R . . C23 C 0.2179(3) 0.55525(14) 0.34986(11) 0.0722(6) Uani 1 1 d . . . H23 H 0.2933 0.5931 0.3323 0.087 Uiso 1 1 calc R . . C24 C 0.2628(2) 0.46528(13) 0.38183(10) 0.0562(4) Uani 1 1 d . . . C25 C -0.1293(2) 0.39279(14) 0.43900(10) 0.0610(5) Uani 1 1 d . . . H25A H -0.1665 0.3368 0.4094 0.091 Uiso 1 1 calc R . . H25B H -0.2179 0.4352 0.4419 0.091 Uiso 1 1 calc R . . H25C H -0.0811 0.3713 0.4871 0.091 Uiso 1 1 calc R . . C26 C 0.4288(2) 0.42561(17) 0.38525(14) 0.0839(7) Uani 1 1 d . . . H26A H 0.4849 0.4258 0.4349 0.126 Uiso 1 1 calc R . . H26B H 0.4849 0.4660 0.3563 0.126 Uiso 1 1 calc R . . H26C H 0.4226 0.3597 0.3668 0.126 Uiso 1 1 calc R . . N1 N 0.36666(18) 0.04611(11) 0.58273(7) 0.0572(4) Uani 1 1 d . . . N2 N 0.18815(15) 0.31963(9) 0.44375(7) 0.0465(3) Uani 1 1 d . . . O1 O 0.00393(19) -0.15726(9) 0.35383(7) 0.0738(4) Uani 1 1 d . . . O2 O 0.04972(15) 0.21923(8) 0.35383(6) 0.0627(4) Uani 1 1 d . . . O3 O 0.35141(15) 0.37460(9) 0.54844(6) 0.0623(3) 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 0.0710(11) 0.0451(10) 0.0495(9) 0.0097(8) 0.0202(9) 0.0125(8) C2 0.1105(17) 0.0469(11) 0.0578(11) 0.0164(9) 0.0250(11) 0.0200(10) C3 0.1231(18) 0.0364(10) 0.0649(12) 0.0094(9) 0.0351(12) 0.0074(10) C4 0.0875(14) 0.0419(10) 0.0561(10) -0.0006(8) 0.0304(10) -0.0030(9) C5 0.0679(11) 0.0393(9) 0.0524(10) 0.0035(7) 0.0166(8) 0.0016(8) C6 0.0571(10) 0.0390(9) 0.0499(9) 0.0050(7) 0.0160(8) 0.0071(7) C7 0.0475(9) 0.0387(8) 0.0478(9) 0.0044(7) 0.0054(7) 0.0059(7) C8 0.0512(9) 0.0373(9) 0.0495(9) 0.0013(7) 0.0010(8) 0.0020(7) C9 0.0428(9) 0.0453(9) 0.0486(9) 0.0009(8) 0.0003(7) 0.0026(7) C10 0.0448(9) 0.0464(9) 0.0465(9) 0.0036(7) 0.0050(7) 0.0060(7) C11 0.0483(9) 0.0551(11) 0.0469(9) 0.0088(8) 0.0089(7) 0.0104(8) C12 0.0498(10) 0.0666(12) 0.0417(9) 0.0116(8) 0.0057(7) 0.0048(8) C13 0.0660(12) 0.0658(12) 0.0522(10) 0.0063(9) 0.0047(9) 0.0062(9) C14 0.0980(16) 0.0758(14) 0.0519(11) 0.0010(10) 0.0137(11) -0.0076(12) C15 0.0816(16) 0.120(2) 0.0448(10) 0.0068(12) -0.0007(11) -0.0187(14) C16 0.0620(13) 0.146(2) 0.0496(11) 0.0156(13) -0.0013(10) 0.0107(14) C17 0.0579(11) 0.1004(16) 0.0492(10) 0.0144(10) 0.0075(9) 0.0187(11) C18 0.1065(17) 0.0596(12) 0.0621(12) -0.0072(10) 0.0210(12) -0.0170(11) C19 0.0499(9) 0.0320(8) 0.0452(8) 0.0004(6) 0.0019(7) 0.0008(7) C20 0.0521(10) 0.0414(9) 0.0432(8) -0.0036(7) 0.0022(7) 0.0034(7) C21 0.0745(12) 0.0475(10) 0.0608(11) 0.0004(9) 0.0054(9) 0.0196(9) C22 0.1156(19) 0.0393(10) 0.0699(13) 0.0104(9) 0.0193(13) 0.0131(11) C23 0.0999(16) 0.0445(11) 0.0786(13) 0.0056(9) 0.0327(12) -0.0141(11) C24 0.0596(11) 0.0473(10) 0.0628(10) -0.0037(8) 0.0143(9) -0.0080(8) C25 0.0528(11) 0.0661(12) 0.0639(11) -0.0050(9) 0.0103(9) -0.0032(8) C26 0.0591(12) 0.0844(15) 0.1133(17) -0.0077(13) 0.0296(12) -0.0099(11) N1 0.0679(9) 0.0551(9) 0.0488(8) 0.0114(7) 0.0119(7) 0.0158(7) N2 0.0486(8) 0.0342(7) 0.0511(8) 0.0030(6) -0.0048(6) 0.0013(6) O1 0.1161(11) 0.0411(7) 0.0678(8) -0.0053(6) 0.0269(8) -0.0133(7) O2 0.0784(9) 0.0435(7) 0.0553(7) 0.0025(5) -0.0158(6) -0.0006(6) O3 0.0690(8) 0.0511(7) 0.0592(7) -0.0025(6) -0.0075(6) -0.0073(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 C1 N1 1.364(2) . ? C1 C2 1.420(3) . ? C1 C6 1.424(2) . ? C2 C3 1.353(3) . ? C2 H2 0.9300 . ? C3 C4 1.414(3) . ? C3 H3 0.9300 . ? C4 O1 1.359(2) . ? C4 C5 1.365(2) . ? C5 C6 1.410(2) . ? C5 H5 0.9300 . ? C6 C7 1.400(2) . ? C7 C10 1.372(2) . ? C7 C8 1.492(2) . ? C8 O2 1.2070(18) . ? C8 N2 1.391(2) . ? C9 O3 1.2045(19) . ? C9 N2 1.4058(19) . ? C9 C10 1.494(2) . ? C10 C11 1.419(2) . ? C11 N1 1.328(2) . ? C11 C12 1.486(2) . ? C12 C13 1.381(3) . ? C12 C17 1.384(2) . ? C13 C14 1.389(3) . ? C13 H13 0.9300 . ? C14 C15 1.368(3) . ? C14 H14 0.9300 . ? C15 C16 1.363(3) . ? C15 H15 0.9300 . ? C16 C17 1.379(3) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 O1 1.431(2) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 C24 1.390(2) . ? C19 C20 1.392(2) . ? C19 N2 1.4385(19) . ? C20 C21 1.385(2) . ? C20 C25 1.499(2) . ? C21 C22 1.371(3) . ? C21 H21 0.9300 . ? C22 C23 1.368(3) . ? C22 H22 0.9300 . ? C23 C24 1.385(3) . ? C23 H23 0.9300 . ? C24 C26 1.503(3) . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 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 N1 C1 C2 118.88(16) . . ? N1 C1 C6 123.85(15) . . ? C2 C1 C6 117.27(17) . . ? C3 C2 C1 120.73(18) . . ? C3 C2 H2 119.6 . . ? C1 C2 H2 119.6 . . ? C2 C3 C4 121.33(17) . . ? C2 C3 H3 119.3 . . ? C4 C3 H3 119.3 . . ? O1 C4 C5 124.96(17) . . ? O1 C4 C3 114.80(16) . . ? C5 C4 C3 120.23(18) . . ? C4 C5 C6 119.19(16) . . ? C4 C5 H5 120.4 . . ? C6 C5 H5 120.4 . . ? C7 C6 C5 124.65(15) . . ? C7 C6 C1 114.18(15) . . ? C5 C6 C1 121.16(15) . . ? C10 C7 C6 121.94(14) . . ? C10 C7 C8 108.87(14) . . ? C6 C7 C8 129.16(14) . . ? O2 C8 N2 125.44(14) . . ? O2 C8 C7 128.88(15) . . ? N2 C8 C7 105.68(13) . . ? O3 C9 N2 123.51(15) . . ? O3 C9 C10 130.74(15) . . ? N2 C9 C10 105.74(13) . . ? C7 C10 C11 120.11(15) . . ? C7 C10 C9 107.92(13) . . ? C11 C10 C9 131.86(15) . . ? N1 C11 C10 119.45(15) . . ? N1 C11 C12 117.44(14) . . ? C10 C11 C12 123.11(16) . . ? C13 C12 C17 118.69(17) . . ? C13 C12 C11 121.29(15) . . ? C17 C12 C11 120.02(17) . . ? C12 C13 C14 120.36(18) . . ? C12 C13 H13 119.8 . . ? C14 C13 H13 119.8 . . ? C15 C14 C13 120.0(2) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C16 C15 C14 120.0(2) . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? C15 C16 C17 120.6(2) . . ? C15 C16 H16 119.7 . . ? C17 C16 H16 119.7 . . ? C16 C17 C12 120.3(2) . . ? C16 C17 H17 119.8 . . ? C12 C17 H17 119.8 . . ? O1 C18 H18A 109.5 . . ? O1 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O1 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C24 C19 C20 122.77(15) . . ? C24 C19 N2 119.25(14) . . ? C20 C19 N2 117.98(14) . . ? C21 C20 C19 117.39(16) . . ? C21 C20 C25 120.39(16) . . ? C19 C20 C25 122.21(15) . . ? C22 C21 C20 120.93(18) . . ? C22 C21 H21 119.5 . . ? C20 C21 H21 119.5 . . ? C23 C22 C21 120.44(17) . . ? C23 C22 H22 119.8 . . ? C21 C22 H22 119.8 . . ? C22 C23 C24 121.29(18) . . ? C22 C23 H23 119.4 . . ? C24 C23 H23 119.4 . . ? C23 C24 C19 117.11(17) . . ? C23 C24 C26 121.15(18) . . ? C19 C24 C26 121.73(16) . . ? C20 C25 H25A 109.5 . . ? C20 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C20 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C24 C26 H26A 109.5 . . ? C24 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C24 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C11 N1 C1 120.21(14) . . ? C8 N2 C9 111.74(12) . . ? C8 N2 C19 123.99(12) . . ? C9 N2 C19 124.26(13) . . ? C4 O1 C18 117.05(14) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.162 _refine_diff_density_min -0.142 _refine_diff_density_rms 0.031 _database_code_depnum_ccdc_archive 'CCDC 945281' ####################################################################### # # 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_120903c_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H17 Cl N2 O2' _chemical_formula_weight 412.86 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' Cl Cl 0.1484 0.1585 '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 15.341(3) _cell_length_b 8.1615(13) _cell_length_c 17.193(3) _cell_angle_alpha 90.00 _cell_angle_beta 105.999(2) _cell_angle_gamma 90.00 _cell_volume 2069.3(6) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3271 _cell_measurement_theta_min 2.76 _cell_measurement_theta_max 24.33 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.325 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 0.209 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9575 _exptl_absorpt_correction_T_max 0.9896 _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 10331 _diffrn_reflns_av_R_equivalents 0.0223 _diffrn_reflns_av_sigmaI/netI 0.0265 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 25.04 _reflns_number_total 3663 _reflns_number_gt 2939 _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^)+(0.0404P)^2^+0.5959P] 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 3663 _refine_ls_number_parameters 273 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0584 _refine_ls_R_factor_gt 0.0457 _refine_ls_wR_factor_ref 0.1106 _refine_ls_wR_factor_gt 0.1012 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _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 0.33820(12) 0.7963(3) -0.03214(11) 0.0434(5) Uani 1 1 d . . . C2 C 0.35105(14) 0.9639(3) -0.03898(13) 0.0529(5) Uani 1 1 d . . . C3 C 0.34697(15) 1.0235(3) -0.11565(15) 0.0634(6) Uani 1 1 d . . . H3 H 0.3550 1.1349 -0.1226 0.076 Uiso 1 1 calc R . . C4 C 0.33141(16) 0.9213(4) -0.18091(15) 0.0697(7) Uani 1 1 d . . . H4 H 0.3286 0.9640 -0.2317 0.084 Uiso 1 1 calc R . . C5 C 0.31989(16) 0.7568(4) -0.17237(14) 0.0681(7) Uani 1 1 d . . . H5 H 0.3096 0.6889 -0.2174 0.082 Uiso 1 1 calc R . . C6 C 0.32326(14) 0.6895(3) -0.09719(13) 0.0532(5) Uani 1 1 d . . . C7 C 0.3702(2) 1.0751(3) 0.03309(17) 0.0865(8) Uani 1 1 d . . . H7A H 0.4271 1.0457 0.0702 0.130 Uiso 1 1 calc R . . H7B H 0.3228 1.0646 0.0593 0.130 Uiso 1 1 calc R . . H7C H 0.3729 1.1864 0.0158 0.130 Uiso 1 1 calc R . . C8 C 0.31337(19) 0.5083(3) -0.08603(17) 0.0782(8) Uani 1 1 d . . . H8A H 0.3661 0.4679 -0.0465 0.117 Uiso 1 1 calc R . . H8B H 0.3073 0.4532 -0.1366 0.117 Uiso 1 1 calc R . . H8C H 0.2605 0.4882 -0.0679 0.117 Uiso 1 1 calc R . . C9 C 0.26600(12) 0.6902(2) 0.07284(11) 0.0426(5) Uani 1 1 d . . . C10 C 0.30318(12) 0.6143(2) 0.15434(11) 0.0404(4) Uani 1 1 d . . . C11 C 0.39558(12) 0.6220(2) 0.17394(11) 0.0432(5) Uani 1 1 d . . . C12 C 0.42295(13) 0.6908(3) 0.10418(12) 0.0491(5) Uani 1 1 d . . . C13 C 0.25951(12) 0.5441(2) 0.20867(11) 0.0426(5) Uani 1 1 d . . . C14 C 0.40038(13) 0.5066(3) 0.30225(11) 0.0463(5) Uani 1 1 d . . . C15 C 0.44912(15) 0.4522(3) 0.37997(12) 0.0588(6) Uani 1 1 d . . . H15 H 0.4183 0.4100 0.4151 0.071 Uiso 1 1 calc R . . C16 C 0.54095(16) 0.4613(3) 0.40347(13) 0.0680(7) Uani 1 1 d . . . H16 H 0.5724 0.4261 0.4550 0.082 Uiso 1 1 calc R . . C17 C 0.58940(15) 0.5226(3) 0.35171(14) 0.0671(7) Uani 1 1 d . . . H17 H 0.6523 0.5279 0.3693 0.080 Uiso 1 1 calc R . . C18 C 0.54520(14) 0.5745(3) 0.27584(13) 0.0585(6) Uani 1 1 d . . . H18 H 0.5777 0.6139 0.2414 0.070 Uiso 1 1 calc R . . C19 C 0.44943(13) 0.5682(3) 0.24980(11) 0.0452(5) Uani 1 1 d . . . C20 C 0.15983(13) 0.5222(3) 0.18944(11) 0.0468(5) Uani 1 1 d . . . C21 C 0.11094(14) 0.4318(3) 0.12350(13) 0.0551(6) Uani 1 1 d . . . C22 C 0.01792(16) 0.4147(4) 0.10648(16) 0.0744(8) Uani 1 1 d . . . H22 H -0.0141 0.3545 0.0618 0.089 Uiso 1 1 calc R . . C23 C -0.02652(17) 0.4883(4) 0.1567(2) 0.0869(9) Uani 1 1 d . . . H23 H -0.0892 0.4792 0.1453 0.104 Uiso 1 1 calc R . . C24 C 0.02065(18) 0.5748(4) 0.22340(19) 0.0823(8) Uani 1 1 d . . . H24 H -0.0099 0.6220 0.2576 0.099 Uiso 1 1 calc R . . C25 C 0.11297(15) 0.5916(3) 0.23975(14) 0.0618(6) Uani 1 1 d . . . H25 H 0.1446 0.6503 0.2851 0.074 Uiso 1 1 calc R . . Cl1 Cl 0.16735(5) 0.32788(9) 0.06348(4) 0.0764(2) Uani 1 1 d . . . N1 N 0.34241(10) 0.7300(2) 0.04613(9) 0.0459(4) Uani 1 1 d . . . N2 N 0.30760(11) 0.4937(2) 0.28117(9) 0.0483(4) Uani 1 1 d . . . O1 O 0.49777(9) 0.7078(2) 0.09544(9) 0.0705(5) Uani 1 1 d . . . O2 O 0.18934(9) 0.71639(19) 0.03420(8) 0.0537(4) 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 0.0349(10) 0.0530(13) 0.0428(11) 0.0092(9) 0.0119(8) 0.0008(9) C2 0.0447(12) 0.0549(14) 0.0588(13) 0.0063(10) 0.0137(10) -0.0005(10) C3 0.0537(14) 0.0659(16) 0.0719(16) 0.0252(13) 0.0192(11) -0.0010(12) C4 0.0607(15) 0.096(2) 0.0578(15) 0.0258(15) 0.0251(12) 0.0068(14) C5 0.0671(15) 0.092(2) 0.0471(13) -0.0025(13) 0.0194(11) 0.0058(14) C6 0.0498(12) 0.0571(14) 0.0525(12) 0.0010(10) 0.0140(10) 0.0036(10) C7 0.110(2) 0.0613(17) 0.0845(19) -0.0098(14) 0.0208(17) -0.0029(16) C8 0.0923(19) 0.0570(16) 0.0829(18) -0.0069(13) 0.0201(15) 0.0018(14) C9 0.0358(11) 0.0501(12) 0.0414(10) 0.0039(9) 0.0098(8) -0.0012(9) C10 0.0330(10) 0.0474(11) 0.0385(10) 0.0021(8) 0.0061(8) -0.0018(8) C11 0.0374(10) 0.0490(12) 0.0416(10) 0.0034(9) 0.0080(8) -0.0014(9) C12 0.0368(11) 0.0597(14) 0.0497(12) 0.0079(10) 0.0102(9) -0.0035(10) C13 0.0389(10) 0.0485(12) 0.0393(10) 0.0011(9) 0.0089(8) -0.0029(9) C14 0.0457(11) 0.0513(12) 0.0379(10) -0.0013(9) 0.0048(8) 0.0011(9) C15 0.0594(14) 0.0703(16) 0.0417(11) 0.0080(11) 0.0056(10) 0.0049(12) C16 0.0618(15) 0.0849(18) 0.0456(13) 0.0062(12) -0.0048(11) 0.0134(13) C17 0.0430(12) 0.0917(19) 0.0575(14) 0.0030(13) -0.0012(10) 0.0092(12) C18 0.0402(11) 0.0794(17) 0.0509(12) 0.0029(11) 0.0042(9) 0.0036(11) C19 0.0387(11) 0.0523(12) 0.0410(10) -0.0002(9) 0.0047(8) 0.0002(9) C20 0.0384(11) 0.0578(13) 0.0441(11) 0.0128(9) 0.0111(9) -0.0042(9) C21 0.0453(12) 0.0655(15) 0.0524(12) 0.0113(11) 0.0097(9) -0.0099(10) C22 0.0503(14) 0.089(2) 0.0736(16) 0.0215(15) 0.0003(12) -0.0221(13) C23 0.0393(13) 0.114(3) 0.108(2) 0.036(2) 0.0199(15) -0.0035(15) C24 0.0547(16) 0.104(2) 0.098(2) 0.0184(18) 0.0380(15) 0.0064(15) C25 0.0534(13) 0.0767(17) 0.0610(14) 0.0109(12) 0.0253(11) -0.0011(12) Cl1 0.0799(5) 0.0776(5) 0.0718(4) -0.0202(3) 0.0214(3) -0.0229(3) N1 0.0343(8) 0.0610(11) 0.0418(9) 0.0119(8) 0.0096(7) -0.0013(8) N2 0.0461(10) 0.0573(11) 0.0399(9) 0.0036(8) 0.0090(7) -0.0022(8) O1 0.0354(8) 0.1062(14) 0.0703(10) 0.0227(9) 0.0153(7) -0.0034(8) O2 0.0341(7) 0.0752(11) 0.0482(8) 0.0119(7) 0.0055(6) 0.0028(7) _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 C6 1.387(3) . ? C1 C2 1.391(3) . ? C1 N1 1.435(2) . ? C2 C3 1.390(3) . ? C2 C7 1.498(3) . ? C3 C4 1.365(4) . ? C3 H3 0.9300 . ? C4 C5 1.368(4) . ? C4 H4 0.9300 . ? C5 C6 1.392(3) . ? C5 H5 0.9300 . ? C6 C8 1.504(3) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 O2 1.200(2) . ? C9 N1 1.410(2) . ? C9 C10 1.494(3) . ? C10 C11 1.365(2) . ? C10 C13 1.412(2) . ? C11 C19 1.408(3) . ? C11 C12 1.486(3) . ? C12 O1 1.206(2) . ? C12 N1 1.395(2) . ? C13 N2 1.327(2) . ? C13 C20 1.484(3) . ? C14 N2 1.373(2) . ? C14 C15 1.411(3) . ? C14 C19 1.416(3) . ? C15 C16 1.356(3) . ? C15 H15 0.9300 . ? C16 C17 1.400(3) . ? C16 H16 0.9300 . ? C17 C18 1.361(3) . ? C17 H17 0.9300 . ? C18 C19 1.414(3) . ? C18 H18 0.9300 . ? C20 C21 1.387(3) . ? C20 C25 1.389(3) . ? C21 C22 1.382(3) . ? C21 Cl1 1.739(2) . ? C22 C23 1.377(4) . ? C22 H22 0.9300 . ? C23 C24 1.371(4) . ? C23 H23 0.9300 . ? C24 C25 1.373(3) . ? C24 H24 0.9300 . ? C25 H25 0.9300 . ? 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 C6 C1 C2 123.07(19) . . ? C6 C1 N1 118.28(19) . . ? C2 C1 N1 118.63(18) . . ? C3 C2 C1 117.0(2) . . ? C3 C2 C7 121.3(2) . . ? C1 C2 C7 121.7(2) . . ? C4 C3 C2 121.2(2) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.4 . . ? C3 C4 C5 120.7(2) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C4 C5 C6 120.9(2) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? C1 C6 C5 117.2(2) . . ? C1 C6 C8 121.0(2) . . ? C5 C6 C8 121.8(2) . . ? C2 C7 H7A 109.5 . . ? C2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O2 C9 N1 123.70(17) . . ? O2 C9 C10 130.98(17) . . ? N1 C9 C10 105.32(15) . . ? C11 C10 C13 120.33(17) . . ? C11 C10 C9 108.33(16) . . ? C13 C10 C9 131.33(16) . . ? C10 C11 C19 121.24(17) . . ? C10 C11 C12 108.87(16) . . ? C19 C11 C12 129.89(17) . . ? O1 C12 N1 124.75(19) . . ? O1 C12 C11 129.39(18) . . ? N1 C12 C11 105.82(16) . . ? N2 C13 C10 120.32(17) . . ? N2 C13 C20 116.36(16) . . ? C10 C13 C20 123.31(16) . . ? N2 C14 C15 117.78(18) . . ? N2 C14 C19 123.61(17) . . ? C15 C14 C19 118.60(19) . . ? C16 C15 C14 120.0(2) . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? C15 C16 C17 121.3(2) . . ? C15 C16 H16 119.3 . . ? C17 C16 H16 119.3 . . ? C18 C17 C16 120.6(2) . . ? C18 C17 H17 119.7 . . ? C16 C17 H17 119.7 . . ? C17 C18 C19 119.4(2) . . ? C17 C18 H18 120.3 . . ? C19 C18 H18 120.3 . . ? C11 C19 C18 125.10(19) . . ? C11 C19 C14 114.92(17) . . ? C18 C19 C14 119.97(18) . . ? C21 C20 C25 118.03(19) . . ? C21 C20 C13 122.55(19) . . ? C25 C20 C13 119.41(19) . . ? C22 C21 C20 121.4(2) . . ? C22 C21 Cl1 118.6(2) . . ? C20 C21 Cl1 119.93(16) . . ? C23 C22 C21 118.9(3) . . ? C23 C22 H22 120.5 . . ? C21 C22 H22 120.5 . . ? C24 C23 C22 120.7(2) . . ? C24 C23 H23 119.6 . . ? C22 C23 H23 119.6 . . ? C23 C24 C25 120.0(3) . . ? C23 C24 H24 120.0 . . ? C25 C24 H24 120.0 . . ? C24 C25 C20 120.9(2) . . ? C24 C25 H25 119.5 . . ? C20 C25 H25 119.5 . . ? C12 N1 C9 111.48(15) . . ? C12 N1 C1 124.03(15) . . ? C9 N1 C1 124.45(15) . . ? C13 N2 C14 119.45(16) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.04 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.154 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.037 _database_code_depnum_ccdc_archive 'CCDC 945282'