# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2001 data_5h _database_code_CSD 164198 _journal_coden_Cambridge 207 _publ_contact_author 'Dr Vishnu Ji Ram' _publ_contact_author_adress ; Dr Vishnu Ji Ram Division of Medicinal Chemistry Central Drug Research Institute Lucknow 226 001 INDIA ; _publ_contact_author_email 'ROOT@CSCDRI.REN.NIC.IN' loop_ _publ_author_name _publ_author_address 'Ram, Vishnu Ji.' ;Medicinal Chemistry Division Central Drug Research Institute Chattar Manzil Palace, Post Box No. 173 Lucknow-226 001 India ; 'Srivastava, Pratibha' ;Medicinal Chemistry Division Central Drug Research Institute Chattar Manzil Palace, Post Box No. 173 Lucknow-226 001 India ; 'Agarwal, Nidhi' ;Medicinal Chemistry Division Central Drug Research Institute Chattar Manzil Palace, Post Box No. 173 Lucknow-226 001 India ; _journal_name_full 'J. Chem. Soc., Perkin Trans. 1' _chemical_name_systematic ; 3-cyano-6-(4-chlorophenyl)-4-[Bis(4-fluorophenyl)piperazino]-2H-pyran-2-one ; _chemical_name_common ? _chemical_melting_point 220 _chemical_formula_moiety ? _chemical_formula_sum 'C29 H22 Cl F2 N3 O2' _chemical_formula_weight 517.95 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'Cl' 'Cl' 0.1484 0.1585 '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' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'C' 'C' 0.0033 0.0016 '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' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 44.292(4) _cell_length_b 7.6620(10) _cell_length_c 14.9490(10) _cell_angle_alpha 90.00 _cell_angle_beta 92.71 _cell_angle_gamma 90.00 _cell_volume 5067.5(9) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 47 _cell_measurement_theta_min 2.7 _cell_measurement_theta_max 12.3 _exptl_crystal_description plate _exptl_crystal_colour yellowish _exptl_crystal_size_max 0.375 _exptl_crystal_size_mid 0.275 _exptl_crystal_size_min 0.075 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.358 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2144 _exptl_absorpt_coefficient_mu 0.198 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method \q-2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% nil _diffrn_reflns_number 5388 _diffrn_reflns_av_R_equivalents 0.0330 _diffrn_reflns_av_sigmaI/netI 0.0717 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 52 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 1 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.70 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4445 _reflns_number_gt 2219 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=3D1/[\s^2^(Fo^2^)+(0.0710P)^2^+0.0000P] where P=3D(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 4445 _refine_ls_number_parameters 334 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1369 _refine_ls_R_factor_gt 0.0584 _refine_ls_wR_factor_ref 0.1572 _refine_ls_wR_factor_gt 0.1240 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _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 Cl1 Cl 0.15179(2) 0.70573(15) 0.08105(7) 0.0842(4) Uani 1 1 d . . . O1 O 0.26872(5) 0.4406(3) -0.14185(13) 0.0691(7) Uani 1 1 d . . . N7 N 0.34658(6) 0.3351(4) 0.01443(15) 0.0541(8) Uani 1 1 d . . . N10 N 0.39519(5) 0.2378(3) 0.13966(14) 0.0471(7) Uani 1 1 d . . . C13 C 0.41092(7) 0.1292(4) 0.20872(18) 0.0461(8) Uani 1 1 d . . . H13 H 0.3973 0.0351 0.2254 0.055 Uiso 1 1 calc R . . F1 F 0.44894(6) 0.5015(3) 0.51621(14) 0.1165(10) Uani 1 1 d . . . C14 C 0.41923(7) 0.2356(4) 0.29150(19) 0.0451(8) Uani 1 1 d . . . C3 C 0.32055(7) 0.3462(4) -0.13379(19) 0.0487(8) Uani 1 1 d . . . C2 C 0.29388(8) 0.3892(5) -0.1863(2) 0.0658(10) Uani 1 1 d . . . C6 C 0.26959(7) 0.4598(4) -0.0509(2) 0.0510(9) Uani 1 1 d . . . C26 C 0.24075(7) 0.5183(4) -0.0182(2) 0.0513(9) Uani 1 1 d . . . O34 O 0.29126(6) 0.3878(4) -0.26702(15) 0.0952(10) Uani 1 1 d . . . C4 C 0.32215(7) 0.3688(4) -0.04005(19) 0.0461(8) Uani 1 1 d . . . C17 C 0.43907(8) 0.4122(6) 0.4422(2) 0.0689(11) Uani 1 1 d . . . C27 C 0.23620(8) 0.5325(5) 0.0727(2) 0.0644(10) Uani 1 1 d . . . H27 H 0.2518 0.5040 0.1138 0.077 Uiso 1 1 calc R . . C32 C 0.34461(9) 0.2993(5) -0.1893(2) 0.0610(10) Uani 1 1 d . . . C30 C 0.18970(8) 0.6231(5) -0.0471(2) 0.0651(10) Uani 1 1 d . . . H30 H 0.1741 0.6541 -0.0877 0.078 Uiso 1 1 calc R . . C5 C 0.29502(7) 0.4271(4) -0.0020(2) 0.0509(9) Uani 1 1 d . . . H5 H 0.2950 0.4430 0.0597 0.061 Uiso 1 1 calc R . . C20 C 0.43957(7) 0.0486(5) 0.17629(19) 0.0504(9) Uani 1 1 d . . . C11 C 0.36602(8) 0.2968(5) 0.16939(19) 0.0596(10) Uani 1 1 d . . . H11A H 0.3688 0.3549 0.2268 0.072 Uiso 1 1 calc R . . H11B H 0.3529 0.1969 0.1770 0.072 Uiso 1 1 calc R . . C9 C 0.38951(7) 0.1441(5) 0.05569(18) 0.0583(10) Uani 1 1 d . . . H9A H 0.3767 0.0440 0.0661 0.070 Uiso 1 1 calc R . . H9B H 0.4085 0.1015 0.0345 0.070 Uiso 1 1 calc R . . C8 C 0.37445(7) 0.2581(5) -0.01487(19) 0.0610(10) Uani 1 1 d . . . H8A H 0.3882 0.3506 -0.0303 0.073 Uiso 1 1 calc R . . H8B H 0.3700 0.1893 -0.0683 0.073 Uiso 1 1 calc R . . C19 C 0.42692(8) 0.4083(5) 0.2877(2) 0.0639(10) Uani 1 1 d . . . H19 H 0.4253 0.4655 0.2328 0.077 Uiso 1 1 calc R . . C18 C 0.43693(9) 0.4996(5) 0.3622(2) 0.0767(12) Uani 1 1 d . . . H18 H 0.4421 0.6170 0.3585 0.092 Uiso 1 1 calc R . . C29 C 0.18596(8) 0.6343(5) 0.0425(2) 0.0610(10) Uani 1 1 d . . . F2 F 0.51976(6) -0.1634(4) 0.10351(16) 0.1349(12) Uani 1 1 d . . . C28 C 0.20904(9) 0.5878(5) 0.1030(2) 0.0684(11) Uani 1 1 d . . . H28 H 0.2062 0.5939 0.1642 0.082 Uiso 1 1 calc R . . C31 C 0.21689(8) 0.5655(5) -0.0771(2) 0.0597(10) Uani 1 1 d . . . H31 H 0.2194 0.5579 -0.1384 0.072 Uiso 1 1 calc R . . C15 C 0.42153(7) 0.1548(5) 0.3733(2) 0.0582(10) Uani 1 1 d . . . H15 H 0.4163 0.0377 0.3775 0.070 Uiso 1 1 calc R . . C25 C 0.44497(9) -0.1272(5) 0.1863(2) 0.0653(10) Uani 1 1 d . . . H25 H 0.4302 -0.1986 0.2090 0.078 Uiso 1 1 calc R . . N33 N 0.36262(8) 0.2636(5) -0.2389(2) 0.0871(11) Uani 1 1 d . . . C12 C 0.35144(8) 0.4195(5) 0.10296(19) 0.0651(11) Uani 1 1 d . . . H12A H 0.3322 0.4578 0.1242 0.078 Uiso 1 1 calc R . . H12B H 0.3642 0.5215 0.0971 0.078 Uiso 1 1 calc R . . C16 C 0.43150(9) 0.2434(6) 0.4496(2) 0.0723(11) Uani 1 1 d . . . H16 H 0.4329 0.1873 0.5048 0.087 Uiso 1 1 calc R . . C24 C 0.47233(12) -0.1996(6) 0.1628(3) 0.0851(14) Uani 1 1 d . . . H24 H 0.4762 -0.3180 0.1709 0.102 Uiso 1 1 calc R . . C23 C 0.49320(11) -0.0929(8) 0.1277(3) 0.0847(15) Uani 1 1 d . . . C22 C 0.48882(10) 0.0806(8) 0.1164(3) 0.0872(14) Uani 1 1 d . . . H22 H 0.5036 0.1507 0.0928 0.105 Uiso 1 1 calc R . . C21 C 0.46188(9) 0.1497(6) 0.1408(2) 0.0726(11) Uani 1 1 d . . . H21 H 0.4585 0.2687 0.1332 0.087 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0652(7) 0.0915(8) 0.0965(7) -0.0148(6) 0.0093(5) -0.0034(6) O1 0.0606(15) 0.104(2) 0.0403(13) -0.0089(13) -0.0182(11) 0.0069(15) N7 0.0524(17) 0.073(2) 0.0359(14) -0.0031(14) -0.0126(12) 0.0086(16) N10 0.0474(16) 0.0606(18) 0.0324(13) -0.0022(13) -0.0091(11) 0.0071(14) C13 0.0479(19) 0.048(2) 0.0413(17) 0.0054(16) -0.0106(15) -0.0048(17) F1 0.166(2) 0.109(2) 0.0697(15) -0.0348(14) -0.0456(15) -0.0033(18) C14 0.0397(18) 0.055(2) 0.0395(18) 0.0002(16) -0.0071(14) 0.0006(17) C3 0.049(2) 0.055(2) 0.0410(18) -0.0008(16) -0.0104(16) -0.0017(18) C2 0.064(2) 0.090(3) 0.042(2) -0.010(2) -0.0105(18) 0.001(2) C6 0.057(2) 0.055(2) 0.0402(18) 0.0039(16) -0.0121(16) -0.0086(18) C26 0.048(2) 0.055(2) 0.050(2) -0.0003(17) -0.0116(16) -0.0104(18) O34 0.0832(18) 0.163(3) 0.0379(14) -0.0127(16) -0.0179(12) 0.025(2) C4 0.051(2) 0.046(2) 0.0404(18) 0.0015(15) -0.0122(15) -0.0005(17) C17 0.077(3) 0.081(3) 0.046(2) -0.022(2) -0.0209(18) 0.006(2) C27 0.060(2) 0.079(3) 0.053(2) 0.002(2) -0.0108(18) -0.006(2) C32 0.071(3) 0.069(3) 0.0413(19) 0.0064(19) -0.0162(19) 0.007(2) C30 0.050(2) 0.078(3) 0.065(2) 0.002(2) -0.0140(18) 0.002(2) C5 0.055(2) 0.058(2) 0.0380(17) 0.0001(16) -0.0110(16) -0.0033(19) C20 0.057(2) 0.057(3) 0.0355(17) -0.0001(17) -0.0113(16) 0.005(2) C11 0.058(2) 0.085(3) 0.0348(16) -0.0097(18) -0.0109(15) 0.011(2) C9 0.060(2) 0.073(3) 0.0408(18) -0.0077(18) -0.0126(16) 0.012(2) C8 0.056(2) 0.089(3) 0.0370(17) -0.0026(19) -0.0099(15) 0.012(2) C19 0.086(3) 0.056(3) 0.047(2) 0.0041(19) -0.0160(18) -0.009(2) C18 0.100(3) 0.055(2) 0.071(3) -0.006(2) -0.028(2) -0.007(2) C29 0.052(2) 0.065(3) 0.066(2) -0.002(2) -0.0008(18) -0.014(2) F2 0.106(2) 0.201(3) 0.0954(18) -0.0224(19) -0.0131(15) 0.092(2) C28 0.070(3) 0.084(3) 0.051(2) -0.002(2) 0.004(2) -0.012(2) C31 0.058(2) 0.071(3) 0.0486(19) 0.0032(19) -0.0099(17) -0.002(2) C15 0.064(2) 0.068(2) 0.0415(18) 0.0044(18) -0.0094(16) -0.010(2) C25 0.082(3) 0.061(3) 0.050(2) -0.0049(19) -0.0227(19) 0.011(2) N33 0.092(3) 0.118(3) 0.0505(18) 0.010(2) 0.0012(18) 0.026(2) C12 0.068(2) 0.083(3) 0.0425(18) -0.0146(19) -0.0227(16) 0.015(2) C16 0.085(3) 0.090(3) 0.040(2) 0.000(2) -0.0087(18) -0.007(3) C24 0.108(4) 0.083(3) 0.061(3) -0.013(2) -0.033(3) 0.042(3) C23 0.075(3) 0.127(5) 0.050(2) -0.014(3) -0.015(2) 0.054(3) C22 0.065(3) 0.125(5) 0.072(3) 0.016(3) 0.006(2) 0.028(3) C21 0.068(3) 0.084(3) 0.066(2) 0.014(2) 0.003(2) 0.013(3) _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 C29 1.733(4) . ? O1 C6 1.366(3) . ? O1 C2 1.381(4) . ? N7 C4 1.348(4) . ? N7 C8 1.454(4) . ? N7 C12 1.479(4) . ? N10 C11 1.458(4) . ? N10 C9 1.458(4) . ? N10 C13 1.475(4) . ? C13 C20 1.511(4) . ? C13 C14 1.513(4) . ? C13 H13 0.9800 . ? F1 C17 1.356(4) . ? C14 C19 1.368(4) . ? C14 C15 1.370(4) . ? C3 C4 1.411(4) . ? C3 C32 1.427(5) . ? C3 C2 1.425(4) . ? C2 O34 1.207(4) . ? C6 C5 1.338(4) . ? C6 C26 1.460(5) . ? C26 C27 1.387(4) . ? C26 C31 1.391(4) . ? C4 C5 1.426(4) . ? C17 C16 1.342(5) . ? C17 C18 1.370(5) . ? C27 C28 1.372(5) . ? C27 H27 0.9300 . ? C32 N33 1.148(4) . ? C30 C29 1.361(4) . ? C30 C31 1.377(5) . ? C30 H30 0.9300 . ? C5 H5 0.9300 . ? C20 C25 1.375(5) . ? C20 C21 1.382(5) . ? C11 C12 1.492(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C9 C8 1.502(4) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C19 C18 1.371(5) . ? C19 H19 0.9300 . ? C18 H18 0.9300 . ? C29 C28 1.379(5) . ? F2 C23 1.359(4) . ? C28 H28 0.9300 . ? C31 H31 0.9300 . ? C15 C16 1.382(5) . ? C15 H15 0.9300 . ? C25 C24 1.393(5) . ? C25 H25 0.9300 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C16 H16 0.9300 . ? C24 C23 1.357(6) . ? C24 H24 0.9300 . ? C23 C22 1.353(6) . ? C22 C21 1.370(5) . ? C22 H22 0.9300 . ? C21 H21 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 O1 C2 121.6(2) . . ? C4 N7 C8 124.3(2) . . ? C4 N7 C12 122.4(3) . . ? C8 N7 C12 110.9(2) . . ? C11 N10 C9 107.2(2) . . ? C11 N10 C13 111.0(2) . . ? C9 N10 C13 112.4(2) . . ? N10 C13 C20 112.4(2) . . ? N10 C13 C14 110.9(3) . . ? C20 C13 C14 107.9(2) . . ? N10 C13 H13 108.5 . . ? C20 C13 H13 108.5 . . ? C14 C13 H13 108.5 . . ? C19 C14 C15 117.8(3) . . ? C19 C14 C13 122.6(3) . . ? C15 C14 C13 119.4(3) . . ? C4 C3 C32 127.2(3) . . ? C4 C3 C2 121.3(3) . . ? C32 C3 C2 111.1(3) . . ? O34 C2 O1 116.2(3) . . ? O34 C2 C3 125.9(3) . . ? O1 C2 C3 117.9(3) . . ? C5 C6 O1 120.5(3) . . ? C5 C6 C26 127.0(3) . . ? O1 C6 C26 112.5(3) . . ? C27 C26 C31 117.3(3) . . ? C27 C26 C6 121.5(3) . . ? C31 C26 C6 121.2(3) . . ? N7 C4 C3 125.3(3) . . ? N7 C4 C5 119.1(3) . . ? C3 C4 C5 115.6(3) . . ? C16 C17 F1 119.4(4) . . ? C16 C17 C18 122.4(3) . . ? F1 C17 C18 118.2(4) . . ? C28 C27 C26 121.2(3) . . ? C28 C27 H27 119.4 . . ? C26 C27 H27 119.4 . . ? N33 C32 C3 175.3(3) . . ? C29 C30 C31 119.3(3) . . ? C29 C30 H30 120.3 . . ? C31 C30 H30 120.3 . . ? C6 C5 C4 123.0(3) . . ? C6 C5 H5 118.5 . . ? C4 C5 H5 118.5 . . ? C25 C20 C21 117.9(4) . . ? C25 C20 C13 120.7(3) . . ? C21 C20 C13 121.4(3) . . ? N10 C11 C12 110.8(3) . . ? N10 C11 H11A 109.5 . . ? C12 C11 H11A 109.5 . . ? N10 C11 H11B 109.5 . . ? C12 C11 H11B 109.5 . . ? H11A C11 H11B 108.1 . . ? N10 C9 C8 111.8(3) . . ? N10 C9 H9A 109.3 . . ? C8 C9 H9A 109.3 . . ? N10 C9 H9B 109.3 . . ? C8 C9 H9B 109.3 . . ? H9A C9 H9B 107.9 . . ? N7 C8 C9 112.3(2) . . ? N7 C8 H8A 109.1 . . ? C9 C8 H8A 109.1 . . ? N7 C8 H8B 109.1 . . ? C9 C8 H8B 109.1 . . ? H8A C8 H8B 107.9 . . ? C14 C19 C18 122.1(3) . . ? C14 C19 H19 119.0 . . ? C18 C19 H19 119.0 . . ? C17 C18 C19 117.8(4) . . ? C17 C18 H18 121.1 . . ? C19 C18 H18 121.1 . . ? C30 C29 C28 120.5(3) . . ? C30 C29 Cl1 119.7(3) . . ? C28 C29 Cl1 119.7(3) . . ? C27 C28 C29 119.9(3) . . ? C27 C28 H28 120.1 . . ? C29 C28 H28 120.1 . . ? C30 C31 C26 121.8(3) . . ? C30 C31 H31 119.1 . . ? C26 C31 H31 119.1 . . ? C14 C15 C16 121.5(4) . . ? C14 C15 H15 119.3 . . ? C16 C15 H15 119.3 . . ? C20 C25 C24 120.8(4) . . ? C20 C25 H25 119.6 . . ? C24 C25 H25 119.6 . . ? N7 C12 C11 111.1(3) . . ? N7 C12 H12A 109.4 . . ? C11 C12 H12A 109.4 . . ? N7 C12 H12B 109.4 . . ? C11 C12 H12B 109.4 . . ? H12A C12 H12B 108.0 . . ? C17 C16 C15 118.4(4) . . ? C17 C16 H16 120.8 . . ? C15 C16 H16 120.8 . . ? C23 C24 C25 118.3(4) . . ? C23 C24 H24 120.8 . . ? C25 C24 H24 120.8 . . ? C22 C23 C24 122.9(4) . . ? C22 C23 F2 118.5(6) . . ? C24 C23 F2 118.5(5) . . ? C23 C22 C21 117.9(5) . . ? C23 C22 H22 121.0 . . ? C21 C22 H22 121.0 . . ? C22 C21 C20 122.2(4) . . ? C22 C21 H21 118.9 . . ? C20 C21 H21 118.9 . . ? 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 C11 N10 C13 C20 173.4(3) . . . . ? C9 N10 C13 C20 53.4(3) . . . . ? C11 N10 C13 C14 -65.7(3) . . . . ? C9 N10 C13 C14 174.3(3) . . . . ? N10 C13 C14 C19 -33.4(4) . . . . ? C20 C13 C14 C19 90.1(4) . . . . ? N10 C13 C14 C15 151.8(3) . . . . ? C20 C13 C14 C15 -84.6(4) . . . . ? C6 O1 C2 O34 -175.1(3) . . . . ? C6 O1 C2 C3 3.7(5) . . . . ? C4 C3 C2 O34 173.5(4) . . . . ? C32 C3 C2 O34 -0.2(6) . . . . ? C4 C3 C2 O1 -5.1(5) . . . . ? C32 C3 C2 O1 -178.8(3) . . . . ? C2 O1 C6 C5 -0.8(5) . . . . ? C2 O1 C6 C26 178.8(3) . . . . ? C5 C6 C26 C27 -5.6(6) . . . . ? O1 C6 C26 C27 174.8(3) . . . . ? C5 C6 C26 C31 173.1(3) . . . . ? O1 C6 C26 C31 -6.5(5) . . . . ? C8 N7 C4 C3 -4.6(5) . . . . ? C12 N7 C4 C3 156.4(3) . . . . ? C8 N7 C4 C5 173.3(3) . . . . ? C12 N7 C4 C5 -25.7(5) . . . . ? C32 C3 C4 N7 -5.9(6) . . . . ? C2 C3 C4 N7 -178.5(3) . . . . ? C32 C3 C4 C5 176.1(3) . . . . ? C2 C3 C4 C5 3.5(5) . . . . ? C31 C26 C27 C28 1.2(5) . . . . ? C6 C26 C27 C28 179.9(3) . . . . ? C4 C3 C32 N33 -173(5) . . . . ? C2 C3 C32 N33 0(6) . . . . ? O1 C6 C5 C4 -1.0(5) . . . . ? C26 C6 C5 C4 179.5(3) . . . . ? N7 C4 C5 C6 -178.5(3) . . . . ? C3 C4 C5 C6 -0.4(5) . . . . ? N10 C13 C20 C25 -129.7(3) . . . . ? C14 C13 C20 C25 107.7(3) . . . . ? N10 C13 C20 C21 54.2(4) . . . . ? C14 C13 C20 C21 -68.4(4) . . . . ? C9 N10 C11 C12 -62.0(4) . . . . ? C13 N10 C11 C12 174.9(3) . . . . ? C11 N10 C9 C8 59.7(4) . . . . ? C13 N10 C9 C8 -178.1(3) . . . . ? C4 N7 C8 C9 -146.7(3) . . . . ? C12 N7 C8 C9 50.4(4) . . . . ? N10 C9 C8 N7 -55.6(4) . . . . ? C15 C14 C19 C18 0.6(5) . . . . ? C13 C14 C19 C18 -174.2(3) . . . . ? C16 C17 C18 C19 -0.6(6) . . . . ? F1 C17 C18 C19 180.0(3) . . . . ? C14 C19 C18 C17 -0.1(6) . . . . ? C31 C30 C29 C28 -0.3(6) . . . . ? C31 C30 C29 Cl1 -179.7(3) . . . . ? C26 C27 C28 C29 -1.5(6) . . . . ? C30 C29 C28 C27 1.1(6) . . . . ? Cl1 C29 C28 C27 -179.5(3) . . . . ? C29 C30 C31 C26 -0.1(6) . . . . ? C27 C26 C31 C30 -0.4(5) . . . . ? C6 C26 C31 C30 -179.1(3) . . . . ? C19 C14 C15 C16 -0.5(5) . . . . ? C13 C14 C15 C16 174.5(3) . . . . ? C21 C20 C25 C24 1.2(5) . . . . ? C13 C20 C25 C24 -175.0(3) . . . . ? C4 N7 C12 C11 144.3(3) . . . . ? C8 N7 C12 C11 -52.5(4) . . . . ? N10 C11 C12 N7 59.5(4) . . . . ? F1 C17 C16 C15 -179.9(3) . . . . ? C18 C17 C16 C15 0.7(6) . . . . ? C14 C15 C16 C17 -0.2(6) . . . . ? C20 C25 C24 C23 -1.6(5) . . . . ? C25 C24 C23 C22 1.4(6) . . . . ? C25 C24 C23 F2 -179.1(3) . . . . ? C24 C23 C22 C21 -0.7(6) . . . . ? F2 C23 C22 C21 179.8(3) . . . . ? C23 C22 C21 C20 0.2(6) . . . . ? C25 C20 C21 C22 -0.5(5) . . . . ? C13 C20 C21 C22 175.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.172 _refine_diff_density_min -0.297 _refine_diff_density_rms 0.043 data_6q _database_code_CSD 164199 _journal_coden_Cambridge 207 _publ_contact_author 'Dr Vishnu Ji Ram' _publ_contact_author_adress ; Dr Vishnu Ji Ram Division of Medicinal Chemistry Central Drug Research Institute Lucknow 226 001 INDIA ; _publ_contact_author_email 'ROOT@CSCDRI.REN.NIC.IN' loop_ _publ_author_name _publ_author_address 'Ram, Vishnu Ji.' ;Medicinal Chemistry Division Central Drug Research Institute Chattar Manzil Palace, Post Box No. 173 Lucknow-226 001 India ; 'Srivastava, Pratibha' ;Medicinal Chemistry Division Central Drug Research Institute Chattar Manzil Palace, Post Box No. 173 Lucknow-226 001 India ; 'Agarwal, Nidhi' ;Medicinal Chemistry Division Central Drug Research Institute Chattar Manzil Palace, Post Box No. 173 Lucknow-226 001 India ; _journal_name_full 'J. Chem. Soc., Perkin Trans. 1' _chemical_name_systematic ; 4-(4-chlorophenyl)-2-(2-pyridyl piperazino)-6-cyclopropyl benzonitrile ; _chemical_name_common ? _chemical_melting_point 152 _chemical_formula_moiety ? _chemical_formula_sum 'C25 H23 Cl N4' _chemical_formula_weight 414.92 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.4520(10) _cell_length_b 12.3980(10) _cell_length_c 21.137(2) _cell_angle_alpha 75.020(10) _cell_angle_beta 83.190(10) _cell_angle_gamma 81.700(10) _cell_volume 2109.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 41 _cell_measurement_theta_min 4.9 _cell_measurement_theta_max 12.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.425 _exptl_crystal_size_mid 0.352 _exptl_crystal_size_min 0.200 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.306 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 872 _exptl_absorpt_coefficient_mu 0.201 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method \q-2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% nil _diffrn_reflns_number 8892 _diffrn_reflns_av_R_equivalents 0.0277 _diffrn_reflns_av_sigmaI/netI 0.0360 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 1 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 25.00 _reflns_number_total 7258 _reflns_number_gt 5254 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=3D1/[\s^2^(Fo^2^)+(0.0816P)^2^+1.7264P] where P=3D(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0073(12) _refine_ls_extinction_expression 'Fc^*^=3DkFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 7258 _refine_ls_number_parameters 542 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0821 _refine_ls_R_factor_gt 0.0554 _refine_ls_wR_factor_ref 0.1705 _refine_ls_wR_factor_gt 0.1427 _refine_ls_goodness_of_fit_ref 0.962 _refine_ls_restrained_S_all 0.962 _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 Cl2 Cl 0.23611(11) -0.14447(6) 0.35340(4) 0.0679(3) Uani 1 1 d . . . Cl1 Cl 0.77644(15) 0.06110(7) 0.45923(6) 0.0976(4) Uani 1 1 d . . . N19 N 1.1454(3) 0.82048(19) 0.07096(10) 0.0468(5) Uani 1 1 d . . . N46 N 0.5842(3) 0.52767(17) 0.12626(10) 0.0441(5) Uani 1 1 d . . . N16 N 0.9767(3) 0.75627(19) 0.19757(10) 0.0447(5) Uani 1 1 d . . . C2 C 0.9197(3) 0.7088(2) 0.26210(12) 0.0428(6) Uani 1 1 d . . . N49 N 0.6844(3) 0.61240(18) -0.00924(10) 0.0465(5) Uani 1 1 d . . . C5 C 0.7981(3) 0.6217(2) 0.39138(13) 0.0478(6) Uani 1 1 d . . . H5 H 0.7587 0.5919 0.4344 0.057 Uiso 1 1 calc R . . C3 C 0.9059(3) 0.5944(2) 0.28601(13) 0.0465(6) Uani 1 1 d . . . H3 H 0.9385 0.5465 0.2583 0.056 Uiso 1 1 calc R . . C58 C 0.5264(3) 0.6602(2) 0.21795(13) 0.0476(6) Uani 1 1 d . . . C36 C 0.5125(3) 0.4810(2) 0.18900(12) 0.0426(6) Uani 1 1 d . . . C34 C 0.4093(3) 0.3270(2) 0.27187(13) 0.0447(6) Uani 1 1 d . . . N27 N 1.2992(3) 0.9492(2) 0.00027(12) 0.0600(6) Uani 1 1 d . . . C31 C 0.4801(3) 0.5478(2) 0.23524(13) 0.0427(6) Uani 1 1 d . . . C4 C 0.8450(3) 0.5499(2) 0.34994(13) 0.0443(6) Uani 1 1 d . . . C52 C 0.7674(3) 0.6623(2) -0.06814(13) 0.0466(6) Uani 1 1 d . . . C35 C 0.4775(3) 0.3705(2) 0.20894(13) 0.0453(6) Uani 1 1 d . . . H35 H 0.5001 0.3248 0.1796 0.054 Uiso 1 1 calc R . . C22 C 1.2019(3) 0.8699(2) 0.00710(12) 0.0438(6) Uani 1 1 d . . . C33 C 0.3749(3) 0.3953(2) 0.31603(13) 0.0482(6) Uani 1 1 d . . . H33 H 0.3281 0.3662 0.3580 0.058 Uiso 1 1 calc R . . C1 C 0.8683(3) 0.7794(2) 0.30536(13) 0.0431(6) Uani 1 1 d . . . C28 C 0.8685(3) 0.8989(2) 0.28206(13) 0.0483(6) Uani 1 1 d . . . C40 C 0.3694(3) 0.2092(2) 0.29313(12) 0.0436(6) Uani 1 1 d . . . C6 C 0.8084(3) 0.7356(2) 0.37061(13) 0.0451(6) Uani 1 1 d . . . C41 C 0.2300(4) 0.1836(2) 0.33289(14) 0.0509(7) Uani 1 1 d . . . H41 H 0.1628 0.2406 0.3470 0.061 Uiso 1 1 calc R . . C15 C 0.7917(4) 0.3636(2) 0.33589(15) 0.0537(7) Uani 1 1 d . . . H15 H 0.7751 0.3970 0.2921 0.064 Uiso 1 1 calc R . . C42 C 0.1894(4) 0.0756(2) 0.35177(14) 0.0532(7) Uani 1 1 d . . . H42 H 0.0958 0.0597 0.3785 0.064 Uiso 1 1 calc R . . C43 C 0.2889(4) -0.0083(2) 0.33065(13) 0.0500(7) Uani 1 1 d . . . C32 C 0.4091(3) 0.5059(2) 0.29871(13) 0.0455(6) Uani 1 1 d . . . C21 C 1.1266(3) 0.8068(3) 0.18898(13) 0.0508(7) Uani 1 1 d . . . H21A H 1.2164 0.7479 0.1958 0.061 Uiso 1 1 calc R . . H21B H 1.1246 0.8500 0.2214 0.061 Uiso 1 1 calc R . . C50 C 0.5920(3) 0.6858(2) 0.02925(14) 0.0508(7) Uani 1 1 d . . . H50A H 0.5256 0.7444 0.0008 0.061 Uiso 1 1 calc R . . H50B H 0.6649 0.7214 0.0473 0.061 Uiso 1 1 calc R . . C48 C 0.7680(3) 0.5107(2) 0.03098(13) 0.0499(7) Uani 1 1 d . . . H48A H 0.8563 0.5309 0.0492 0.060 Uiso 1 1 calc R . . H48B H 0.8124 0.4603 0.0034 0.060 Uiso 1 1 calc R . . N53 N 0.8658(3) 0.5920(2) -0.09727(12) 0.0594(6) Uani 1 1 d . . . C18 C 1.0042(4) 0.7616(3) 0.08077(13) 0.0529(7) Uani 1 1 d . . . H18A H 1.0135 0.7154 0.0495 0.063 Uiso 1 1 calc R . . H18B H 0.9096 0.8161 0.0725 0.063 Uiso 1 1 calc R . . C23 C 1.1661(4) 0.8370(3) -0.04691(14) 0.0578(7) Uani 1 1 d . . . H23 H 1.0984 0.7820 -0.0416 0.069 Uiso 1 1 calc R . . C47 C 0.6575(3) 0.4504(2) 0.08643(13) 0.0495(7) Uani 1 1 d . . . H47A H 0.5747 0.4235 0.0685 0.059 Uiso 1 1 calc R . . H47B H 0.7181 0.3861 0.1135 0.059 Uiso 1 1 calc R . . N29 N 0.8652(3) 0.9945(2) 0.26557(13) 0.0635(7) Uani 1 1 d . . . C10 C 0.8337(3) 0.4273(2) 0.37496(13) 0.0467(6) Uani 1 1 d . . . C39 C 0.2343(4) 0.5609(3) 0.39682(15) 0.0591(8) Uani 1 1 d . . . H39A H 0.1748 0.6276 0.4078 0.071 Uiso 1 1 calc R . . H39B H 0.1698 0.5020 0.3974 0.071 Uiso 1 1 calc R . . C45 C 0.4682(4) 0.1221(2) 0.27334(14) 0.0534(7) Uani 1 1 d . . . H45 H 0.5625 0.1372 0.2470 0.064 Uiso 1 1 calc R . . C51 C 0.4867(3) 0.6213(2) 0.08457(13) 0.0510(7) Uani 1 1 d . . . H51A H 0.4318 0.6712 0.1109 0.061 Uiso 1 1 calc R . . H51B H 0.4062 0.5920 0.0666 0.061 Uiso 1 1 calc R . . C20 C 1.1487(4) 0.8825(3) 0.12106(13) 0.0534(7) Uani 1 1 d . . . H20A H 1.0639 0.9450 0.1156 0.064 Uiso 1 1 calc R . . H20B H 1.2505 0.9127 0.1156 0.064 Uiso 1 1 calc R . . N59 N 0.5594(3) 0.7497(2) 0.20618(14) 0.0660(7) Uani 1 1 d . . . C54 C 0.9463(4) 0.6364(3) -0.15446(15) 0.0668(9) Uani 1 1 d . . . H54 H 1.0129 0.5872 -0.1753 0.080 Uiso 1 1 calc R . . C12 C 0.8464(5) 0.2616(3) 0.46508(16) 0.0715(10) Uani 1 1 d . . . H12 H 0.8667 0.2269 0.5084 0.086 Uiso 1 1 calc R . . C44 C 0.4285(4) 0.0133(2) 0.29229(15) 0.0570(7) Uani 1 1 d . . . H44 H 0.4960 -0.0446 0.2791 0.068 Uiso 1 1 calc R . . C11 C 0.8628(4) 0.3740(2) 0.43952(14) 0.0623(8) Uani 1 1 d . . . H11 H 0.8941 0.4150 0.4661 0.075 Uiso 1 1 calc R . . C57 C 0.7502(4) 0.7777(3) -0.09562(15) 0.0651(8) Uani 1 1 d . . . H57 H 0.6815 0.8262 -0.0749 0.078 Uiso 1 1 calc R . . C26 C 1.3609(4) 0.9958(3) -0.06072(16) 0.0658(9) Uani 1 1 d . . . H26 H 1.4282 1.0510 -0.0655 0.079 Uiso 1 1 calc R . . C37 C 0.3760(4) 0.5766(2) 0.34647(14) 0.0554(7) Uani 1 1 d . . . H37 H 0.4005 0.6543 0.3295 0.067 Uiso 1 1 calc R . . C13 C 0.8000(4) 0.2019(2) 0.42583(17) 0.0618(8) Uani 1 1 d . . . C14 C 0.7741(4) 0.2507(3) 0.36114(17) 0.0615(8) Uani 1 1 d . . . H14 H 0.7452 0.2086 0.3347 0.074 Uiso 1 1 calc R . . C7 C 0.7539(4) 0.8125(2) 0.41454(14) 0.0544(7) Uani 1 1 d . . . H7 H 0.7835 0.8889 0.3974 0.065 Uiso 1 1 calc R . . C17 C 0.9842(4) 0.6880(2) 0.14988(13) 0.0537(7) Uani 1 1 d . . . H17A H 0.8864 0.6528 0.1556 0.064 Uiso 1 1 calc R . . H17B H 1.0739 0.6291 0.1571 0.064 Uiso 1 1 calc R . . C25 C 1.3317(4) 0.9677(3) -0.11564(15) 0.0673(9) Uani 1 1 d . . . H25 H 1.3776 1.0019 -0.1568 0.081 Uiso 1 1 calc R . . C24 C 1.2314(4) 0.8866(3) -0.10807(16) 0.0709(9) Uani 1 1 d . . . H24 H 1.2078 0.8652 -0.1446 0.085 Uiso 1 1 calc R . . C56 C 0.8373(5) 0.8188(3) -0.15417(16) 0.0711(9) Uani 1 1 d . . . H56 H 0.8271 0.8957 -0.1733 0.085 Uiso 1 1 calc R . . C55 C 0.9377(4) 0.7479(3) -0.18416(15) 0.0660(9) Uani 1 1 d . . . H55 H 0.9981 0.7746 -0.2234 0.079 Uiso 1 1 calc R . . C38 C 0.3980(4) 0.5269(3) 0.41787(16) 0.0672(9) Uani 1 1 d . . . H38A H 0.4336 0.4470 0.4315 0.081 Uiso 1 1 calc R . . H38B H 0.4386 0.5726 0.4418 0.081 Uiso 1 1 calc R . . C8 C 0.7425(5) 0.7731(3) 0.48688(16) 0.0779(11) Uani 1 1 d . . . H8A H 0.7715 0.6936 0.5058 0.094 Uiso 1 1 calc R . . H8B H 0.7701 0.8226 0.5116 0.094 Uiso 1 1 calc R . . C9 C 0.5974(5) 0.8056(4) 0.4541(2) 0.0919(13) Uani 1 1 d . . . H9A H 0.5340 0.8756 0.4582 0.110 Uiso 1 1 calc R . . H9B H 0.5354 0.7466 0.4524 0.110 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 Cl2 0.0927(6) 0.0421(4) 0.0683(5) -0.0094(3) 0.0000(4) -0.0192(4) Cl1 0.1340(9) 0.0440(5) 0.1088(8) -0.0215(5) 0.0399(7) -0.0273(5) N19 0.0456(12) 0.0501(13) 0.0436(12) -0.0101(10) 0.0024(10) -0.0097(10) N46 0.0450(12) 0.0405(12) 0.0413(12) -0.0058(9) 0.0022(9) 0.0001(9) N16 0.0439(12) 0.0506(13) 0.0403(12) -0.0121(10) 0.0035(9) -0.0117(10) C2 0.0388(13) 0.0457(14) 0.0422(14) -0.0100(11) 0.0000(11) -0.0039(11) N49 0.0450(12) 0.0456(12) 0.0436(12) -0.0056(10) 0.0025(10) -0.0025(10) C5 0.0556(16) 0.0439(15) 0.0424(14) -0.0088(12) 0.0045(12) -0.0110(12) C3 0.0502(15) 0.0457(15) 0.0440(14) -0.0155(12) 0.0014(12) -0.0033(12) C58 0.0418(15) 0.0499(17) 0.0492(15) -0.0103(12) 0.0012(12) -0.0068(12) C36 0.0375(13) 0.0428(14) 0.0445(14) -0.0072(11) 0.0000(11) -0.0047(11) C34 0.0444(14) 0.0417(14) 0.0477(15) -0.0124(11) -0.0003(12) -0.0051(11) N27 0.0575(15) 0.0694(16) 0.0533(14) -0.0136(12) 0.0065(12) -0.0197(13) C31 0.0414(14) 0.0377(13) 0.0466(14) -0.0080(11) 0.0005(11) -0.0049(11) C4 0.0451(14) 0.0420(14) 0.0463(14) -0.0130(11) 0.0006(11) -0.0067(11) C52 0.0446(15) 0.0519(16) 0.0426(14) -0.0077(12) -0.0061(12) -0.0084(12) C35 0.0479(15) 0.0447(14) 0.0435(14) -0.0135(11) 0.0025(12) -0.0070(12) C22 0.0404(14) 0.0448(14) 0.0417(14) -0.0068(11) -0.0014(11) 0.0004(11) C33 0.0550(16) 0.0445(14) 0.0443(14) -0.0124(12) 0.0089(12) -0.0110(12) C1 0.0427(14) 0.0422(14) 0.0444(14) -0.0113(11) -0.0002(11) -0.0070(11) C28 0.0510(16) 0.0479(17) 0.0433(14) -0.0095(12) 0.0023(12) -0.0048(12) C40 0.0488(15) 0.0400(14) 0.0423(14) -0.0108(11) 0.0017(11) -0.0094(11) C6 0.0464(15) 0.0413(14) 0.0482(15) -0.0138(11) 0.0034(12) -0.0087(11) C41 0.0556(17) 0.0433(15) 0.0527(16) -0.0135(12) 0.0065(13) -0.0079(12) C15 0.0568(17) 0.0503(16) 0.0563(17) -0.0165(13) -0.0065(14) -0.0062(13) C42 0.0534(17) 0.0490(16) 0.0553(17) -0.0123(13) 0.0114(13) -0.0137(13) C43 0.0652(18) 0.0391(14) 0.0461(15) -0.0092(12) -0.0018(13) -0.0122(13) C32 0.0474(15) 0.0410(14) 0.0493(15) -0.0141(12) -0.0001(12) -0.0064(11) C21 0.0431(15) 0.0637(18) 0.0466(15) -0.0144(13) 0.0015(12) -0.0123(13) C50 0.0500(16) 0.0444(15) 0.0498(15) -0.0032(12) -0.0030(12) 0.0051(12) C48 0.0512(16) 0.0441(15) 0.0473(15) -0.0063(12) 0.0050(12) 0.0005(12) N53 0.0670(16) 0.0593(15) 0.0471(14) -0.0091(11) 0.0070(12) -0.0088(13) C18 0.0578(17) 0.0597(17) 0.0436(15) -0.0140(13) 0.0039(13) -0.0194(14) C23 0.0630(19) 0.0602(18) 0.0492(16) -0.0102(14) 0.0029(14) -0.0163(15) C47 0.0529(16) 0.0430(14) 0.0482(15) -0.0083(12) 0.0044(12) -0.0043(12) N29 0.0770(18) 0.0452(15) 0.0628(16) -0.0073(12) 0.0014(13) -0.0058(13) C10 0.0478(15) 0.0443(14) 0.0486(15) -0.0148(12) 0.0055(12) -0.0090(12) C39 0.0623(19) 0.0547(17) 0.0623(18) -0.0234(14) 0.0121(15) -0.0110(14) C45 0.0543(17) 0.0480(16) 0.0567(17) -0.0156(13) 0.0090(13) -0.0081(13) C51 0.0419(15) 0.0544(16) 0.0504(16) -0.0068(13) -0.0008(12) 0.0017(12) C20 0.0563(17) 0.0585(17) 0.0487(16) -0.0163(13) 0.0069(13) -0.0210(14) N59 0.0637(17) 0.0509(16) 0.0808(19) -0.0082(13) -0.0012(14) -0.0167(13) C54 0.073(2) 0.074(2) 0.0501(17) -0.0153(16) 0.0087(15) -0.0087(17) C12 0.106(3) 0.0491(17) 0.0543(18) -0.0083(14) 0.0107(18) -0.0146(18) C44 0.0640(19) 0.0432(15) 0.0615(18) -0.0157(13) 0.0070(15) -0.0041(13) C11 0.095(2) 0.0491(17) 0.0450(16) -0.0149(13) 0.0073(15) -0.0197(16) C57 0.073(2) 0.0565(18) 0.0556(18) -0.0022(14) 0.0003(16) -0.0009(16) C26 0.065(2) 0.069(2) 0.0610(19) -0.0099(16) 0.0102(16) -0.0230(16) C37 0.072(2) 0.0428(15) 0.0534(17) -0.0157(13) 0.0077(14) -0.0157(14) C13 0.069(2) 0.0438(16) 0.071(2) -0.0209(15) 0.0224(16) -0.0128(14) C14 0.0598(19) 0.0516(17) 0.082(2) -0.0306(16) -0.0031(16) -0.0121(14) C7 0.073(2) 0.0418(15) 0.0483(16) -0.0151(12) 0.0073(14) -0.0106(14) C17 0.0612(18) 0.0551(17) 0.0475(15) -0.0163(13) 0.0079(13) -0.0191(14) C25 0.071(2) 0.076(2) 0.0467(17) -0.0046(15) 0.0124(15) -0.0143(18) C24 0.080(2) 0.085(2) 0.0479(18) -0.0181(16) 0.0053(16) -0.0152(19) C56 0.088(3) 0.063(2) 0.0542(19) 0.0022(16) -0.0027(17) -0.0179(18) C55 0.071(2) 0.080(2) 0.0437(16) -0.0052(16) 0.0011(15) -0.0221(18) C38 0.078(2) 0.074(2) 0.0610(19) -0.0312(17) -0.0062(16) -0.0194(18) C8 0.133(4) 0.0531(19) 0.0491(18) -0.0161(15) 0.005(2) -0.018(2) C9 0.081(3) 0.099(3) 0.112(3) -0.067(3) 0.027(2) -0.017(2) _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 Cl2 C43 1.740(3) . ? Cl1 C13 1.737(3) . ? N19 C22 1.389(3) . ? N19 C18 1.455(3) . ? N19 C20 1.465(3) . ? N46 C36 1.405(3) . ? N46 C47 1.460(3) . ? N46 C51 1.473(3) . ? N16 C2 1.397(3) . ? N16 C17 1.465(3) . ? N16 C21 1.466(3) . ? C2 C3 1.395(4) . ? C2 C1 1.414(4) . ? N49 C52 1.395(3) . ? N49 C50 1.458(3) . ? N49 C48 1.464(3) . ? C5 C6 1.379(4) . ? C5 C4 1.391(4) . ? C5 H5 0.9300 . ? C3 C4 1.388(4) . ? C3 H3 0.9300 . ? C58 N59 1.141(4) . ? C58 C31 1.445(4) . ? C36 C35 1.390(4) . ? C36 C31 1.416(4) . ? C34 C35 1.389(4) . ? C34 C33 1.396(4) . ? C34 C40 1.488(3) . ? N27 C22 1.339(4) . ? N27 C26 1.346(4) . ? C31 C32 1.403(4) . ? C4 C10 1.489(4) . ? C52 N53 1.333(4) . ? C52 C57 1.392(4) . ? C35 H35 0.9300 . ? C22 C23 1.385(4) . ? C33 C32 1.388(4) . ? C33 H33 0.9300 . ? C1 C6 1.407(4) . ? C1 C28 1.435(4) . ? C28 N29 1.144(4) . ? C40 C45 1.389(4) . ? C40 C41 1.389(4) . ? C6 C7 1.488(4) . ? C41 C42 1.376(4) . ? C41 H41 0.9300 . ? C15 C10 1.385(4) . ? C15 C14 1.386(4) . ? C15 H15 0.9300 . ? C42 C43 1.373(4) . ? C42 H42 0.9300 . ? C43 C44 1.369(4) . ? C32 C37 1.479(4) . ? C21 C20 1.505(4) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C50 C51 1.508(4) . ? C50 H50A 0.9700 . ? C50 H50B 0.9700 . ? C48 C47 1.514(4) . ? C48 H48A 0.9700 . ? C48 H48B 0.9700 . ? N53 C54 1.340(4) . ? C18 C17 1.514(4) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C23 C24 1.368(4) . ? C23 H23 0.9300 . ? C47 H47A 0.9700 . ? C47 H47B 0.9700 . ? C10 C11 1.388(4) . ? C39 C38 1.473(5) . ? C39 C37 1.504(4) . ? C39 H39A 0.9700 . ? C39 H39B 0.9700 . ? C45 C44 1.383(4) . ? C45 H45 0.9300 . ? C51 H51A 0.9700 . ? C51 H51B 0.9700 . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C54 C55 1.358(5) . ? C54 H54 0.9300 . ? C12 C13 1.367(5) . ? C12 C11 1.380(4) . ? C12 H12 0.9300 . ? C44 H44 0.9300 . ? C11 H11 0.9300 . ? C57 C56 1.378(4) . ? C57 H57 0.9300 . ? C26 C25 1.354(5) . ? C26 H26 0.9300 . ? C37 C38 1.498(4) . ? C37 H37 0.9800 . ? C13 C14 1.374(5) . ? C14 H14 0.9300 . ? C7 C8 1.476(4) . ? C7 C9 1.480(5) . ? C7 H7 0.9800 . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C25 C24 1.373(5) . ? C25 H25 0.9300 . ? C24 H24 0.9300 . ? C56 C55 1.356(5) . ? C56 H56 0.9300 . ? C55 H55 0.9300 . ? C38 H38A 0.9700 . ? C38 H38B 0.9700 . ? C8 C9 1.436(6) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? 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 C22 N19 C18 118.5(2) . . ? C22 N19 C20 117.3(2) . . ? C18 N19 C20 112.6(2) . . ? C36 N46 C47 117.6(2) . . ? C36 N46 C51 116.1(2) . . ? C47 N46 C51 108.4(2) . . ? C2 N16 C17 117.1(2) . . ? C2 N16 C21 116.5(2) . . ? C17 N16 C21 108.8(2) . . ? C3 C2 N16 123.1(2) . . ? C3 C2 C1 117.6(2) . . ? N16 C2 C1 119.2(2) . . ? C52 N49 C50 118.0(2) . . ? C52 N49 C48 116.1(2) . . ? C50 N49 C48 113.4(2) . . ? C6 C5 C4 122.0(2) . . ? C6 C5 H5 119.0 . . ? C4 C5 H5 119.0 . . ? C4 C3 C2 121.9(2) . . ? C4 C3 H3 119.1 . . ? C2 C3 H3 119.1 . . ? N59 C58 C31 177.6(3) . . ? C35 C36 N46 123.1(2) . . ? C35 C36 C31 118.1(2) . . ? N46 C36 C31 118.8(2) . . ? C35 C34 C33 119.6(2) . . ? C35 C34 C40 121.4(2) . . ? C33 C34 C40 119.0(2) . . ? C22 N27 C26 117.9(3) . . ? C32 C31 C36 121.4(2) . . ? C32 C31 C58 118.9(2) . . ? C36 C31 C58 119.7(2) . . ? C3 C4 C5 118.9(2) . . ? C3 C4 C10 121.1(2) . . ? C5 C4 C10 120.0(2) . . ? N53 C52 C57 121.3(3) . . ? N53 C52 N49 115.7(2) . . ? C57 C52 N49 123.0(3) . . ? C34 C35 C36 121.2(2) . . ? C34 C35 H35 119.4 . . ? C36 C35 H35 119.4 . . ? N27 C22 C23 121.0(2) . . ? N27 C22 N19 116.3(2) . . ? C23 C22 N19 122.6(2) . . ? C32 C33 C34 121.4(2) . . ? C32 C33 H33 119.3 . . ? C34 C33 H33 119.3 . . ? C6 C1 C2 121.2(2) . . ? C6 C1 C28 118.6(2) . . ? C2 C1 C28 120.1(2) . . ? N29 C28 C1 177.5(3) . . ? C45 C40 C41 118.0(2) . . ? C45 C40 C34 121.4(2) . . ? C41 C40 C34 120.6(2) . . ? C5 C6 C1 118.4(2) . . ? C5 C6 C7 121.8(2) . . ? C1 C6 C7 119.8(2) . . ? C42 C41 C40 121.3(3) . . ? C42 C41 H41 119.3 . . ? C40 C41 H41 119.3 . . ? C10 C15 C14 121.0(3) . . ? C10 C15 H15 119.5 . . ? C14 C15 H15 119.5 . . ? C43 C42 C41 119.1(3) . . ? C43 C42 H42 120.4 . . ? C41 C42 H42 120.4 . . ? C44 C43 C42 121.3(3) . . ? C44 C43 Cl2 119.5(2) . . ? C42 C43 Cl2 119.2(2) . . ? C33 C32 C31 118.2(2) . . ? C33 C32 C37 120.9(2) . . ? C31 C32 C37 120.8(2) . . ? N16 C21 C20 110.6(2) . . ? N16 C21 H21A 109.5 . . ? C20 C21 H21A 109.5 . . ? N16 C21 H21B 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 108.1 . . ? N49 C50 C51 111.5(2) . . ? N49 C50 H50A 109.3 . . ? C51 C50 H50A 109.3 . . ? N49 C50 H50B 109.3 . . ? C51 C50 H50B 109.3 . . ? H50A C50 H50B 108.0 . . ? N49 C48 C47 112.0(2) . . ? N49 C48 H48A 109.2 . . ? C47 C48 H48A 109.2 . . ? N49 C48 H48B 109.2 . . ? C47 C48 H48B 109.2 . . ? H48A C48 H48B 107.9 . . ? C52 N53 C54 117.6(3) . . ? N19 C18 C17 111.6(2) . . ? N19 C18 H18A 109.3 . . ? C17 C18 H18A 109.3 . . ? N19 C18 H18B 109.3 . . ? C17 C18 H18B 109.3 . . ? H18A C18 H18B 108.0 . . ? C24 C23 C22 119.2(3) . . ? C24 C23 H23 120.4 . . ? C22 C23 H23 120.4 . . ? N46 C47 C48 109.4(2) . . ? N46 C47 H47A 109.8 . . ? C48 C47 H47A 109.8 . . ? N46 C47 H47B 109.8 . . ? C48 C47 H47B 109.8 . . ? H47A C47 H47B 108.2 . . ? C15 C10 C11 118.1(3) . . ? C15 C10 C4 121.9(3) . . ? C11 C10 C4 119.9(2) . . ? C38 C39 C37 60.4(2) . . ? C38 C39 H39A 117.7 . . ? C37 C39 H39A 117.7 . . ? C38 C39 H39B 117.7 . . ? C37 C39 H39B 117.7 . . ? H39A C39 H39B 114.9 . . ? C44 C45 C40 121.0(3) . . ? C44 C45 H45 119.5 . . ? C40 C45 H45 119.5 . . ? N46 C51 C50 110.2(2) . . ? N46 C51 H51A 109.6 . . ? C50 C51 H51A 109.6 . . ? N46 C51 H51B 109.6 . . ? C50 C51 H51B 109.6 . . ? H51A C51 H51B 108.1 . . ? N19 C20 C21 110.7(2) . . ? N19 C20 H20A 109.5 . . ? C21 C20 H20A 109.5 . . ? N19 C20 H20B 109.5 . . ? C21 C20 H20B 109.5 . . ? H20A C20 H20B 108.1 . . ? N53 C54 C55 124.8(3) . . ? N53 C54 H54 117.6 . . ? C55 C54 H54 117.6 . . ? C13 C12 C11 119.0(3) . . ? C13 C12 H12 120.5 . . ? C11 C12 H12 120.5 . . ? C43 C44 C45 119.2(3) . . ? C43 C44 H44 120.4 . . ? C45 C44 H44 120.4 . . ? C12 C11 C10 121.4(3) . . ? C12 C11 H11 119.3 . . ? C10 C11 H11 119.3 . . ? C56 C57 C52 118.6(3) . . ? C56 C57 H57 120.7 . . ? C52 C57 H57 120.7 . . ? N27 C26 C25 124.3(3) . . ? N27 C26 H26 117.8 . . ? C25 C26 H26 117.8 . . ? C32 C37 C38 120.7(3) . . ? C32 C37 C39 119.8(2) . . ? C38 C37 C39 58.8(2) . . ? C32 C37 H37 115.3 . . ? C38 C37 H37 115.3 . . ? C39 C37 H37 115.3 . . ? C12 C13 C14 121.4(3) . . ? C12 C13 Cl1 118.4(3) . . ? C14 C13 Cl1 120.1(2) . . ? C13 C14 C15 119.0(3) . . ? C13 C14 H14 120.5 . . ? C15 C14 H14 120.5 . . ? C8 C7 C9 58.1(3) . . ? C8 C7 C6 122.6(3) . . ? C9 C7 C6 120.6(3) . . ? C8 C7 H7 114.6 . . ? C9 C7 H7 114.6 . . ? C6 C7 H7 114.6 . . ? N16 C17 C18 109.7(2) . . ? N16 C17 H17A 109.7 . . ? C18 C17 H17A 109.7 . . ? N16 C17 H17B 109.7 . . ? C18 C17 H17B 109.7 . . ? H17A C17 H17B 108.2 . . ? C26 C25 C24 117.3(3) . . ? C26 C25 H25 121.4 . . ? C24 C25 H25 121.4 . . ? C23 C24 C25 120.2(3) . . ? C23 C24 H24 119.9 . . ? C25 C24 H24 119.9 . . ? C55 C56 C57 120.5(3) . . ? C55 C56 H56 119.7 . . ? C57 C56 H56 119.7 . . ? C56 C55 C54 117.2(3) . . ? C56 C55 H55 121.4 . . ? C54 C55 H55 121.4 . . ? C39 C38 C37 60.8(2) . . ? C39 C38 H38A 117.7 . . ? C37 C38 H38A 117.7 . . ? C39 C38 H38B 117.7 . . ? C37 C38 H38B 117.7 . . ? H38A C38 H38B 114.8 . . ? C9 C8 C7 61.1(2) . . ? C9 C8 H8A 117.7 . . ? C7 C8 H8A 117.7 . . ? C9 C8 H8B 117.7 . . ? C7 C8 H8B 117.7 . . ? H8A C8 H8B 114.8 . . ? C8 C9 C7 60.8(2) . . ? C8 C9 H9A 117.7 . . ? C7 C9 H9A 117.7 . . ? C8 C9 H9B 117.7 . . ? C7 C9 H9B 117.7 . . ? H9A C9 H9B 114.8 . . ? 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 C17 N16 C2 C3 15.3(4) . . . . ? C21 N16 C2 C3 -116.0(3) . . . . ? C17 N16 C2 C1 -162.7(2) . . . . ? C21 N16 C2 C1 65.9(3) . . . . ? N16 C2 C3 C4 -178.4(3) . . . . ? C1 C2 C3 C4 -0.3(4) . . . . ? C47 N46 C36 C35 -14.4(4) . . . . ? C51 N46 C36 C35 116.4(3) . . . . ? C47 N46 C36 C31 162.9(2) . . . . ? C51 N46 C36 C31 -66.3(3) . . . . ? C35 C36 C31 C32 -2.4(4) . . . . ? N46 C36 C31 C32 -179.8(2) . . . . ? C35 C36 C31 C58 175.2(2) . . . . ? N46 C36 C31 C58 -2.2(4) . . . . ? N59 C58 C31 C32 -18(8) . . . . ? N59 C58 C31 C36 165(8) . . . . ? C2 C3 C4 C5 -0.7(4) . . . . ? C2 C3 C4 C10 -179.0(2) . . . . ? C6 C5 C4 C3 0.9(4) . . . . ? C6 C5 C4 C10 179.2(3) . . . . ? C50 N49 C52 N53 171.9(2) . . . . ? C48 N49 C52 N53 32.2(4) . . . . ? C50 N49 C52 C57 -8.2(4) . . . . ? C48 N49 C52 C57 -147.9(3) . . . . ? C33 C34 C35 C36 0.1(4) . . . . ? C40 C34 C35 C36 179.1(2) . . . . ? N46 C36 C35 C34 178.8(2) . . . . ? C31 C36 C35 C34 1.4(4) . . . . ? C26 N27 C22 C23 0.0(4) . . . . ? C26 N27 C22 N19 177.6(3) . . . . ? C18 N19 C22 N27 161.1(3) . . . . ? C20 N19 C22 N27 20.6(4) . . . . ? C18 N19 C22 C23 -21.4(4) . . . . ? C20 N19 C22 C23 -161.9(3) . . . . ? C35 C34 C33 C32 -0.8(4) . . . . ? C40 C34 C33 C32 -179.8(3) . . . . ? C3 C2 C1 C6 1.2(4) . . . . ? N16 C2 C1 C6 179.3(2) . . . . ? C3 C2 C1 C28 -175.4(2) . . . . ? N16 C2 C1 C28 2.7(4) . . . . ? C6 C1 C28 N29 -10(8) . . . . ? C2 C1 C28 N29 166(7) . . . . ? C35 C34 C40 C45 38.0(4) . . . . ? C33 C34 C40 C45 -143.1(3) . . . . ? C35 C34 C40 C41 -141.2(3) . . . . ? C33 C34 C40 C41 37.8(4) . . . . ? C4 C5 C6 C1 0.0(4) . . . . ? C4 C5 C6 C7 178.3(3) . . . . ? C2 C1 C6 C5 -1.1(4) . . . . ? C28 C1 C6 C5 175.6(3) . . . . ? C2 C1 C6 C7 -179.4(3) . . . . ? C28 C1 C6 C7 -2.7(4) . . . . ? C45 C40 C41 C42 -0.7(4) . . . . ? C34 C40 C41 C42 178.5(3) . . . . ? C40 C41 C42 C43 -0.1(5) . . . . ? C41 C42 C43 C44 1.2(5) . . . . ? C41 C42 C43 Cl2 -179.0(2) . . . . ? C34 C33 C32 C31 -0.2(4) . . . . ? C34 C33 C32 C37 -178.4(3) . . . . ? C36 C31 C32 C33 1.8(4) . . . . ? C58 C31 C32 C33 -175.9(3) . . . . ? C36 C31 C32 C37 -180.0(3) . . . . ? C58 C31 C32 C37 2.4(4) . . . . ? C2 N16 C21 C20 -163.6(2) . . . . ? C17 N16 C21 C20 61.3(3) . . . . ? C52 N49 C50 C51 169.9(2) . . . . ? C48 N49 C50 C51 -49.4(3) . . . . ? C52 N49 C48 C47 -168.7(2) . . . . ? C50 N49 C48 C47 49.8(3) . . . . ? C57 C52 N53 C54 -0.8(4) . . . . ? N49 C52 N53 C54 179.1(3) . . . . ? C22 N19 C18 C17 165.1(2) . . . . ? C20 N19 C18 C17 -52.6(3) . . . . ? N27 C22 C23 C24 0.0(5) . . . . ? N19 C22 C23 C24 -177.4(3) . . . . ? C36 N46 C47 C48 -163.5(2) . . . . ? C51 N46 C47 C48 62.3(3) . . . . ? N49 C48 C47 N46 -56.1(3) . . . . ? C14 C15 C10 C11 2.1(4) . . . . ? C14 C15 C10 C4 -176.8(3) . . . . ? C3 C4 C10 C15 -37.9(4) . . . . ? C5 C4 C10 C15 143.8(3) . . . . ? C3 C4 C10 C11 143.2(3) . . . . ? C5 C4 C10 C11 -35.0(4) . . . . ? C41 C40 C45 C44 0.4(4) . . . . ? C34 C40 C45 C44 -178.7(3) . . . . ? C36 N46 C51 C50 162.4(2) . . . . ? C47 N46 C51 C50 -62.7(3) . . . . ? N49 C50 C51 N46 55.8(3) . . . . ? C22 N19 C20 C21 -164.9(2) . . . . ? C18 N19 C20 C21 52.4(3) . . . . ? N16 C21 C20 N19 -56.8(3) . . . . ? C52 N53 C54 C55 1.6(5) . . . . ? C42 C43 C44 C45 -1.4(5) . . . . ? Cl2 C43 C44 C45 178.8(2) . . . . ? C40 C45 C44 C43 0.6(5) . . . . ? C13 C12 C11 C10 -0.2(5) . . . . ? C15 C10 C11 C12 -1.8(5) . . . . ? C4 C10 C11 C12 177.1(3) . . . . ? N53 C52 C57 C56 0.1(5) . . . . ? N49 C52 C57 C56 -179.7(3) . . . . ? C22 N27 C26 C25 -0.2(5) . . . . ? C33 C32 C37 C38 35.9(4) . . . . ? C31 C32 C37 C38 -142.3(3) . . . . ? C33 C32 C37 C39 -33.4(4) . . . . ? C31 C32 C37 C39 148.4(3) . . . . ? C38 C39 C37 C32 109.9(3) . . . . ? C11 C12 C13 C14 2.0(5) . . . . ? C11 C12 C13 Cl1 -178.9(3) . . . . ? C12 C13 C14 C15 -1.7(5) . . . . ? Cl1 C13 C14 C15 179.2(2) . . . . ? C10 C15 C14 C13 -0.4(5) . . . . ? C5 C6 C7 C8 23.1(5) . . . . ? C1 C6 C7 C8 -158.6(3) . . . . ? C5 C6 C7 C9 -46.4(5) . . . . ? C1 C6 C7 C9 131.9(3) . . . . ? C2 N16 C17 C18 164.7(2) . . . . ? C21 N16 C17 C18 -60.5(3) . . . . ? N19 C18 C17 N16 56.6(3) . . . . ? N27 C26 C25 C24 0.4(6) . . . . ? C22 C23 C24 C25 0.2(5) . . . . ? C26 C25 C24 C23 -0.4(5) . . . . ? C52 C57 C56 C55 -0.1(5) . . . . ? C57 C56 C55 C54 0.8(5) . . . . ? N53 C54 C55 C56 -1.6(5) . . . . ? C32 C37 C38 C39 -108.5(3) . . . . ? C6 C7 C8 C9 -108.3(4) . . . . ? C6 C7 C9 C8 111.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.618 _refine_diff_density_min -0.588 _refine_diff_density_rms 0.046