# Electronic Supplementary Material (ESI) for Green Chemistry # 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_fin _database_code_depnum_ccdc_archive 'CCDC 888823' #TrackingRef 'Indu CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; trans-3-(2,4-Dichlorophenyl)-2-(4-fluorobenzoyl)- 5-methyl-3,5-dihydrofuro-[3,2-c]quinolin-4(2H)-one ; _chemical_name_common ; trans-3-(2,4-Dichlorophenyl)-2-(4-fluorobenzoyl)- 5-methyl-3,5-dihydrofuro-[3,2-c]quinolin-4(2H)-one ; _chemical_melting_point 255 _chemical_formula_moiety 'C25 H16 Cl2 F N O3' _chemical_formula_sum 'C25 H16 Cl2 F N O3' _chemical_formula_weight 468.29 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' F F 0.0171 0.0103 '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 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 10.017(5) _cell_length_b 7.789(4) _cell_length_c 27.003(15) _cell_angle_alpha 90.00 _cell_angle_beta 95.507(8) _cell_angle_gamma 90.00 _cell_volume 2096.9(19) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5234 _cell_measurement_theta_min 2.11 _cell_measurement_theta_max 28.50 _exptl_crystal_description Block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.483 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 0.348 _exptl_absorpt_correction_type None _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? #========================================================================== # Experimental data _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 'Bruker SMART APEXII area-detector diffractometer' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19311 _diffrn_reflns_av_R_equivalents 0.0505 _diffrn_reflns_av_sigmaI/netI 0.0485 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 28.50 _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 28.50 _diffrn_measured_fraction_theta_full 0.986 _reflns_number_total 5234 _reflns_number_gt 3218 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2008)' _computing_cell_refinement APEX2 _computing_data_reduction 'SAINT (Bruker, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP3 (Farrugia, 1997)' _computing_publication_material 'SHELXL97 and PLATON (Spek, 2009)' _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^)+(0.0486P)^2^+4.5906P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5234 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1226 _refine_ls_R_factor_gt 0.0790 _refine_ls_wR_factor_ref 0.2072 _refine_ls_wR_factor_gt 0.1823 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_restrained_S_all 1.090 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.321 _refine_diff_density_min -0.353 #========================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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 0.04674(16) 0.53507(18) 0.07368(5) 0.0804(5) Uani 1 1 d . . . Cl2 Cl -0.17665(14) -0.0763(2) 0.02746(5) 0.0906(5) Uani 1 1 d . . . O2 O 0.2552(3) 0.2728(4) 0.25587(9) 0.0458(6) Uani 1 1 d . . . O1 O 0.4567(3) 0.4637(4) 0.23200(10) 0.0563(8) Uani 1 1 d . . . F1 F 0.6282(3) 0.3762(5) 0.01616(10) 0.0850(10) Uani 1 1 d . . . O3 O -0.1189(3) 0.5760(4) 0.18927(12) 0.0630(9) Uani 1 1 d . . . N1 N -0.1013(3) 0.5142(4) 0.27295(13) 0.0477(8) Uani 1 1 d . . . C7 C 0.1408(3) 0.3796(5) 0.17795(13) 0.0369(8) Uani 1 1 d . . . C16 C 0.0689(3) 0.4165(5) 0.22332(13) 0.0371(8) Uani 1 1 d . . . C8 C 0.2707(4) 0.2887(5) 0.20324(13) 0.0391(8) Uani 1 1 d . . . C17 C 0.1381(4) 0.3528(4) 0.26416(14) 0.0379(8) Uani 1 1 d . . . C19 C 0.0948(4) 0.3655(5) 0.31272(14) 0.0400(8) Uani 1 1 d . . . C10 C 0.4552(3) 0.3831(5) 0.14782(13) 0.0377(8) Uani 1 1 d . . . C9 C 0.4006(3) 0.3855(5) 0.19705(13) 0.0383(8) Uani 1 1 d . . . C11 C 0.5806(4) 0.4598(5) 0.14408(15) 0.0453(9) Uani 1 1 d . . . H11 H 0.6247 0.5134 0.1718 0.054 Uiso 1 1 calc R . . C6 C 0.0595(3) 0.2684(5) 0.13959(13) 0.0377(8) Uani 1 1 d . . . C24 C -0.0321(4) 0.4434(5) 0.31531(15) 0.0464(9) Uani 1 1 d . . . C13 C 0.5705(5) 0.3790(6) 0.05950(15) 0.0554(11) Uani 1 1 d . . . C15 C 0.3890(4) 0.3045(6) 0.10585(14) 0.0486(10) Uani 1 1 d . . . H15 H 0.3064 0.2518 0.1080 0.058 Uiso 1 1 calc R . . C12 C 0.6394(4) 0.4568(6) 0.10014(17) 0.0548(11) Uani 1 1 d . . . H12 H 0.7233 0.5058 0.0979 0.066 Uiso 1 1 calc R . . C18 C -0.0557(4) 0.5075(5) 0.22565(15) 0.0436(9) Uani 1 1 d . . . C20 C 0.1699(5) 0.3068(5) 0.35589(15) 0.0508(10) Uani 1 1 d . . . H20 H 0.2547 0.2602 0.3538 0.061 Uiso 1 1 calc R . . C5 C 0.0272(4) 0.0988(5) 0.15150(14) 0.0435(9) Uani 1 1 d . . . H5 H 0.0554 0.0565 0.1830 0.052 Uiso 1 1 calc R . . C3 C -0.0878(4) 0.0553(7) 0.07128(16) 0.0552(11) Uani 1 1 d . . . C1 C 0.0137(4) 0.3260(6) 0.09233(14) 0.0476(9) Uani 1 1 d . . . C2 C -0.0597(4) 0.2218(7) 0.05782(15) 0.0556(11) Uani 1 1 d . . . H2 H -0.0892 0.2633 0.0264 0.067 Uiso 1 1 calc R . . C4 C -0.0457(4) -0.0077(6) 0.11748(16) 0.0512(10) Uani 1 1 d . . . H4 H -0.0655 -0.1199 0.1260 0.061 Uiso 1 1 calc R . . C14 C 0.4460(4) 0.3049(6) 0.06131(15) 0.0559(11) Uani 1 1 d . . . H14 H 0.4013 0.2560 0.0330 0.067 Uiso 1 1 calc R . . C21 C 0.1189(6) 0.3178(6) 0.40112(17) 0.0668(14) Uani 1 1 d . . . H21 H 0.1688 0.2792 0.4298 0.080 Uiso 1 1 calc R . . C23 C -0.0829(5) 0.4483(7) 0.36225(18) 0.0642(13) Uani 1 1 d . . . H23 H -0.1678 0.4932 0.3652 0.077 Uiso 1 1 calc R . . C22 C -0.0072(6) 0.3867(7) 0.40370(19) 0.0725(15) Uani 1 1 d . . . H22 H -0.0420 0.3918 0.4344 0.087 Uiso 1 1 calc R . . C25 C -0.2299(5) 0.6031(8) 0.2769(2) 0.0760(16) Uani 1 1 d . . . H25A H -0.2585 0.6575 0.2457 0.114 Uiso 1 1 calc R . . H25B H -0.2187 0.6883 0.3026 0.114 Uiso 1 1 calc R . . H25C H -0.2963 0.5213 0.2848 0.114 Uiso 1 1 calc R . . H7 H 0.169(3) 0.488(5) 0.1621(13) 0.033(9) Uiso 1 1 d . . . H8 H 0.282(4) 0.174(5) 0.1903(13) 0.040(10) 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 Cl1 0.1109(11) 0.0654(8) 0.0608(7) 0.0270(6) -0.0128(7) -0.0036(8) Cl2 0.0748(9) 0.1210(13) 0.0731(9) -0.0432(9) -0.0079(7) -0.0215(9) O2 0.0459(14) 0.0493(16) 0.0423(14) 0.0100(12) 0.0047(11) 0.0128(13) O1 0.0485(16) 0.073(2) 0.0467(16) -0.0214(15) 0.0010(13) -0.0090(15) F1 0.085(2) 0.121(3) 0.0524(16) 0.0024(17) 0.0235(14) 0.010(2) O3 0.0480(17) 0.072(2) 0.0658(19) -0.0090(16) -0.0132(14) 0.0162(16) N1 0.0354(16) 0.0468(19) 0.061(2) -0.0173(16) 0.0028(15) -0.0021(15) C7 0.0321(17) 0.0355(19) 0.0421(19) 0.0057(15) -0.0020(14) -0.0010(15) C16 0.0365(18) 0.0316(18) 0.0426(19) -0.0023(15) 0.0000(15) -0.0014(15) C8 0.0381(19) 0.039(2) 0.0390(19) -0.0014(16) 0.0005(15) 0.0058(16) C17 0.0373(18) 0.0287(18) 0.047(2) 0.0005(15) 0.0022(15) -0.0046(15) C19 0.042(2) 0.0318(18) 0.046(2) -0.0016(15) 0.0040(16) -0.0100(16) C10 0.0338(18) 0.0374(19) 0.0411(19) -0.0036(15) -0.0008(14) 0.0044(15) C9 0.0333(18) 0.040(2) 0.0408(19) -0.0082(16) -0.0019(14) 0.0092(15) C11 0.039(2) 0.047(2) 0.049(2) -0.0058(18) -0.0018(16) 0.0033(17) C6 0.0331(17) 0.045(2) 0.0353(18) 0.0025(15) 0.0025(14) 0.0015(16) C24 0.041(2) 0.041(2) 0.057(2) -0.0132(18) 0.0066(18) -0.0141(17) C13 0.057(3) 0.068(3) 0.043(2) 0.005(2) 0.0105(19) 0.016(2) C15 0.042(2) 0.057(3) 0.046(2) -0.0098(19) -0.0017(17) -0.0023(19) C12 0.042(2) 0.061(3) 0.062(3) 0.004(2) 0.0096(19) 0.003(2) C18 0.0360(19) 0.039(2) 0.054(2) -0.0108(17) -0.0058(17) -0.0021(16) C20 0.064(3) 0.042(2) 0.046(2) 0.0029(18) 0.0027(19) -0.005(2) C5 0.044(2) 0.048(2) 0.0381(19) 0.0018(17) 0.0031(16) -0.0033(18) C3 0.039(2) 0.077(3) 0.049(2) -0.020(2) 0.0032(18) -0.004(2) C1 0.045(2) 0.055(2) 0.042(2) 0.0067(18) 0.0030(17) 0.0055(19) C2 0.044(2) 0.084(3) 0.037(2) -0.002(2) -0.0033(17) 0.004(2) C4 0.047(2) 0.052(3) 0.055(2) -0.009(2) 0.0062(18) -0.0107(19) C14 0.054(3) 0.069(3) 0.043(2) -0.011(2) -0.0019(18) 0.003(2) C21 0.102(4) 0.054(3) 0.044(2) 0.003(2) 0.007(2) -0.016(3) C23 0.061(3) 0.067(3) 0.068(3) -0.019(3) 0.024(2) -0.019(2) C22 0.096(4) 0.072(3) 0.053(3) -0.012(2) 0.026(3) -0.021(3) C25 0.048(3) 0.095(4) 0.083(4) -0.040(3) -0.002(2) 0.019(3) #========================================================================== # MOLECULAR GEOMETRY _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 C1 1.745(5) . ? Cl2 C3 1.744(4) . ? O2 C17 1.365(4) . ? O2 C8 1.450(4) . ? O1 C9 1.215(4) . ? F1 C13 1.354(5) . ? O3 C18 1.238(5) . ? N1 C24 1.393(5) . ? N1 C18 1.398(5) . ? N1 C25 1.476(5) . ? C7 C16 1.507(5) . ? C7 C6 1.525(5) . ? C7 C8 1.578(5) . ? C7 H7 1.00(4) . ? C16 C17 1.340(5) . ? C16 C18 1.442(5) . ? C8 C9 1.526(5) . ? C8 H8 0.97(4) . ? C17 C19 1.424(5) . ? C19 C20 1.402(5) . ? C19 C24 1.417(5) . ? C10 C15 1.398(5) . ? C10 C11 1.403(5) . ? C10 C9 1.486(5) . ? C11 C12 1.375(6) . ? C11 H11 0.9300 . ? C6 C1 1.388(5) . ? C6 C5 1.405(5) . ? C24 C23 1.411(6) . ? C13 C12 1.379(6) . ? C13 C14 1.379(6) . ? C15 C14 1.380(6) . ? C15 H15 0.9300 . ? C12 H12 0.9300 . ? C20 C21 1.371(6) . ? C20 H20 0.9300 . ? C5 C4 1.392(5) . ? C5 H5 0.9300 . ? C3 C4 1.369(6) . ? C3 C2 1.383(7) . ? C1 C2 1.391(6) . ? C2 H2 0.9300 . ? C4 H4 0.9300 . ? C14 H14 0.9300 . ? C21 C22 1.380(8) . ? C21 H21 0.9300 . ? C23 C22 1.377(7) . ? C23 H23 0.9300 . ? C22 H22 0.9300 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 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 C17 O2 C8 107.2(3) . . ? C24 N1 C18 123.7(3) . . ? C24 N1 C25 119.7(4) . . ? C18 N1 C25 116.6(4) . . ? C16 C7 C6 113.2(3) . . ? C16 C7 C8 99.9(3) . . ? C6 C7 C8 113.8(3) . . ? C16 C7 H7 111(2) . . ? C6 C7 H7 110(2) . . ? C8 C7 H7 108(2) . . ? C17 C16 C18 121.8(3) . . ? C17 C16 C7 110.4(3) . . ? C18 C16 C7 127.8(3) . . ? O2 C8 C9 108.8(3) . . ? O2 C8 C7 107.5(3) . . ? C9 C8 C7 114.0(3) . . ? O2 C8 H8 108(2) . . ? C9 C8 H8 107(2) . . ? C7 C8 H8 112(2) . . ? C16 C17 O2 114.7(3) . . ? C16 C17 C19 123.6(3) . . ? O2 C17 C19 121.7(3) . . ? C20 C19 C24 120.7(4) . . ? C20 C19 C17 123.8(4) . . ? C24 C19 C17 115.4(3) . . ? C15 C10 C11 119.1(4) . . ? C15 C10 C9 123.0(3) . . ? C11 C10 C9 117.9(3) . . ? O1 C9 C10 121.2(3) . . ? O1 C9 C8 119.9(3) . . ? C10 C9 C8 118.9(3) . . ? C12 C11 C10 121.0(4) . . ? C12 C11 H11 119.5 . . ? C10 C11 H11 119.5 . . ? C1 C6 C5 116.8(4) . . ? C1 C6 C7 123.3(3) . . ? C5 C6 C7 119.9(3) . . ? N1 C24 C23 122.2(4) . . ? N1 C24 C19 120.5(4) . . ? C23 C24 C19 117.3(4) . . ? F1 C13 C12 118.2(4) . . ? F1 C13 C14 119.1(4) . . ? C12 C13 C14 122.7(4) . . ? C14 C15 C10 120.1(4) . . ? C14 C15 H15 119.9 . . ? C10 C15 H15 119.9 . . ? C11 C12 C13 118.1(4) . . ? C11 C12 H12 120.9 . . ? C13 C12 H12 120.9 . . ? O3 C18 N1 121.5(4) . . ? O3 C18 C16 123.8(4) . . ? N1 C18 C16 114.7(3) . . ? C21 C20 C19 120.3(5) . . ? C21 C20 H20 119.9 . . ? C19 C20 H20 119.9 . . ? C4 C5 C6 121.8(4) . . ? C4 C5 H5 119.1 . . ? C6 C5 H5 119.1 . . ? C4 C3 C2 121.5(4) . . ? C4 C3 Cl2 120.0(4) . . ? C2 C3 Cl2 118.5(3) . . ? C6 C1 C2 122.3(4) . . ? C6 C1 Cl1 120.8(3) . . ? C2 C1 Cl1 117.0(3) . . ? C3 C2 C1 118.6(4) . . ? C3 C2 H2 120.7 . . ? C1 C2 H2 120.7 . . ? C3 C4 C5 118.9(4) . . ? C3 C4 H4 120.5 . . ? C5 C4 H4 120.5 . . ? C13 C14 C15 118.9(4) . . ? C13 C14 H14 120.6 . . ? C15 C14 H14 120.6 . . ? C20 C21 C22 119.4(5) . . ? C20 C21 H21 120.3 . . ? C22 C21 H21 120.3 . . ? C22 C23 C24 120.2(5) . . ? C22 C23 H23 119.9 . . ? C24 C23 H23 119.9 . . ? C23 C22 C21 122.0(5) . . ? C23 C22 H22 119.0 . . ? C21 C22 H22 119.0 . . ? N1 C25 H25A 109.5 . . ? N1 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? N1 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C7 C16 C17 118.6(3) . . . . ? C8 C7 C16 C17 -2.8(4) . . . . ? C6 C7 C16 C18 -62.0(5) . . . . ? C8 C7 C16 C18 176.6(3) . . . . ? C17 O2 C8 C9 120.0(3) . . . . ? C17 O2 C8 C7 -4.0(4) . . . . ? C16 C7 C8 O2 4.0(4) . . . . ? C6 C7 C8 O2 -116.9(3) . . . . ? C16 C7 C8 C9 -116.6(3) . . . . ? C6 C7 C8 C9 122.4(3) . . . . ? C18 C16 C17 O2 -178.8(3) . . . . ? C7 C16 C17 O2 0.6(4) . . . . ? C18 C16 C17 C19 1.3(6) . . . . ? C7 C16 C17 C19 -179.2(3) . . . . ? C8 O2 C17 C16 2.2(4) . . . . ? C8 O2 C17 C19 -177.9(3) . . . . ? C16 C17 C19 C20 -176.7(4) . . . . ? O2 C17 C19 C20 3.5(6) . . . . ? C16 C17 C19 C24 3.2(5) . . . . ? O2 C17 C19 C24 -176.6(3) . . . . ? C15 C10 C9 O1 -175.6(4) . . . . ? C11 C10 C9 O1 6.1(5) . . . . ? C15 C10 C9 C8 3.9(5) . . . . ? C11 C10 C9 C8 -174.4(3) . . . . ? O2 C8 C9 O1 -14.6(5) . . . . ? C7 C8 C9 O1 105.4(4) . . . . ? O2 C8 C9 C10 165.9(3) . . . . ? C7 C8 C9 C10 -74.1(4) . . . . ? C15 C10 C11 C12 -0.7(6) . . . . ? C9 C10 C11 C12 177.6(4) . . . . ? C16 C7 C6 C1 115.3(4) . . . . ? C8 C7 C6 C1 -131.5(4) . . . . ? C16 C7 C6 C5 -64.6(4) . . . . ? C8 C7 C6 C5 48.6(4) . . . . ? C18 N1 C24 C23 -178.2(4) . . . . ? C25 N1 C24 C23 2.1(6) . . . . ? C18 N1 C24 C19 3.0(5) . . . . ? C25 N1 C24 C19 -176.7(4) . . . . ? C20 C19 C24 N1 174.6(3) . . . . ? C17 C19 C24 N1 -5.2(5) . . . . ? C20 C19 C24 C23 -4.3(6) . . . . ? C17 C19 C24 C23 175.9(3) . . . . ? C11 C10 C15 C14 -0.9(6) . . . . ? C9 C10 C15 C14 -179.2(4) . . . . ? C10 C11 C12 C13 1.2(6) . . . . ? F1 C13 C12 C11 179.9(4) . . . . ? C14 C13 C12 C11 0.0(7) . . . . ? C24 N1 C18 O3 -178.2(4) . . . . ? C25 N1 C18 O3 1.5(6) . . . . ? C24 N1 C18 C16 1.6(5) . . . . ? C25 N1 C18 C16 -178.7(4) . . . . ? C17 C16 C18 O3 176.0(4) . . . . ? C7 C16 C18 O3 -3.3(6) . . . . ? C17 C16 C18 N1 -3.7(5) . . . . ? C7 C16 C18 N1 177.0(3) . . . . ? C24 C19 C20 C21 2.7(6) . . . . ? C17 C19 C20 C21 -177.5(4) . . . . ? C1 C6 C5 C4 0.7(6) . . . . ? C7 C6 C5 C4 -179.4(3) . . . . ? C5 C6 C1 C2 -0.5(6) . . . . ? C7 C6 C1 C2 179.6(4) . . . . ? C5 C6 C1 Cl1 179.5(3) . . . . ? C7 C6 C1 Cl1 -0.4(5) . . . . ? C4 C3 C2 C1 0.3(6) . . . . ? Cl2 C3 C2 C1 -178.6(3) . . . . ? C6 C1 C2 C3 0.0(6) . . . . ? Cl1 C1 C2 C3 180.0(3) . . . . ? C2 C3 C4 C5 -0.1(6) . . . . ? Cl2 C3 C4 C5 178.8(3) . . . . ? C6 C5 C4 C3 -0.4(6) . . . . ? F1 C13 C14 C15 178.5(4) . . . . ? C12 C13 C14 C15 -1.6(7) . . . . ? C10 C15 C14 C13 2.0(7) . . . . ? C19 C20 C21 C22 0.2(7) . . . . ? N1 C24 C23 C22 -175.7(4) . . . . ? C19 C24 C23 C22 3.2(6) . . . . ? C24 C23 C22 C21 -0.4(8) . . . . ? C20 C21 C22 C23 -1.3(8) . . . . ? # End of CIF ============================================================