# 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_09041a _database_code_depnum_ccdc_archive 'CCDC 913986' #TrackingRef '15897_web_deposit_cif_file_0_RajeevS.Muthyala_1354658465.09041a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 09041a _chemical_melting_point ? _chemical_formula_moiety 'C30 H18 Cl2 N2 O4, 0.5(C H Cl3)' _chemical_formula_sum 'C30.50 H18.50 Cl3.50 N2 O4' _chemical_formula_weight 601.05 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.4803(8) _cell_length_b 13.4027(14) _cell_length_c 13.7401(14) _cell_angle_alpha 97.0370(10) _cell_angle_beta 95.3740(10) _cell_angle_gamma 104.6630(10) _cell_volume 1311.4(2) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2991 _cell_measurement_theta_min 2.84 _cell_measurement_theta_max 27.42 _exptl_crystal_description Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.522 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 614 _exptl_absorpt_coefficient_mu 0.443 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8256 _exptl_absorpt_correction_T_max 0.8427 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details 'V. Ramalingum / Prof. R. Muthyala - UMR' _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15222 _diffrn_reflns_av_R_equivalents 0.0342 _diffrn_reflns_av_sigmaI/netI 0.0359 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.51 _diffrn_reflns_theta_max 26.37 _reflns_number_total 5334 _reflns_number_gt 3945 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0515P)^2^+0.8206P] 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 5334 _refine_ls_number_parameters 379 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0723 _refine_ls_R_factor_gt 0.0477 _refine_ls_wR_factor_ref 0.1195 _refine_ls_wR_factor_gt 0.1078 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl -0.00690(9) 0.61661(5) 0.07947(4) 0.03645(16) Uani 1 1 d . . . Cl2 Cl 0.51491(10) 0.25015(6) 1.02319(5) 0.0537(2) Uani 1 1 d . . . O1 O 0.5257(2) 0.70525(13) 0.52586(13) 0.0442(5) Uani 1 1 d . . . O2 O 0.5970(3) 0.64237(13) 0.73995(13) 0.0468(5) Uani 1 1 d . . . O3 O -0.0748(2) 0.30397(13) 0.38617(12) 0.0397(4) Uani 1 1 d . . . O4 O 0.1162(3) 0.20796(13) 0.59092(12) 0.0426(4) Uani 1 1 d . . . N1 N 0.1878(2) 0.47706(14) 0.45887(13) 0.0263(4) Uani 1 1 d . . . H1A H 0.1262 0.4133 0.4649 0.032 Uiso 1 1 calc R . . N2 N 0.2969(3) 0.40337(14) 0.65573(13) 0.0278(4) Uani 1 1 d . . . H2A H 0.2134 0.3566 0.6127 0.033 Uiso 1 1 calc R . . C1 C 0.3136(3) 0.52947(16) 0.53691(16) 0.0256(5) Uani 1 1 d . . . C2 C 0.4559(3) 0.63120(17) 0.56485(17) 0.0311(5) Uani 1 1 d . . . C3 C 0.4948(3) 0.59928(17) 0.66471(17) 0.0317(5) Uani 1 1 d . . . C4 C 0.3592(3) 0.49729(17) 0.62709(15) 0.0255(5) Uani 1 1 d . . . C5 C 0.1421(3) 0.51080(17) 0.36933(16) 0.0262(5) Uani 1 1 d . . . C6 C 0.2091(3) 0.61435(17) 0.35603(17) 0.0305(5) Uani 1 1 d . . . H6A H 0.2864 0.6638 0.4084 0.037 Uiso 1 1 calc R . . C7 C 0.1637(3) 0.64547(17) 0.26677(17) 0.0320(5) Uani 1 1 d . . . H7A H 0.2115 0.7160 0.2578 0.038 Uiso 1 1 calc R . . C8 C 0.0497(3) 0.57477(17) 0.19072(16) 0.0290(5) Uani 1 1 d . . . C9 C -0.0189(3) 0.47162(17) 0.20178(16) 0.0285(5) Uani 1 1 d . . . H9A H -0.0975 0.4235 0.1489 0.034 Uiso 1 1 calc R . . C10 C 0.0274(3) 0.43779(17) 0.29103(16) 0.0271(5) Uani 1 1 d . . . C11 C -0.0524(3) 0.32683(17) 0.30301(17) 0.0298(5) Uani 1 1 d . . . C12 C -0.1039(3) 0.24236(17) 0.21636(17) 0.0315(5) Uani 1 1 d . . . C13 C -0.0010(3) 0.24285(18) 0.13733(17) 0.0355(6) Uani 1 1 d . . . H13A H 0.0966 0.3027 0.1330 0.043 Uiso 1 1 calc R . . C14 C -0.0409(4) 0.1556(2) 0.06430(19) 0.0451(7) Uani 1 1 d . . . H14A H 0.0302 0.1553 0.0106 0.054 Uiso 1 1 calc R . . C15 C -0.1846(4) 0.0693(2) 0.0706(2) 0.0504(7) Uani 1 1 d . . . H15A H -0.2117 0.0098 0.0209 0.060 Uiso 1 1 calc R . . C16 C -0.2884(4) 0.06887(19) 0.1478(2) 0.0476(7) Uani 1 1 d . . . H16A H -0.3883 0.0096 0.1506 0.057 Uiso 1 1 calc R . . C17 C -0.2484(4) 0.15423(18) 0.22162(19) 0.0396(6) Uani 1 1 d . . . H17A H -0.3189 0.1531 0.2757 0.047 Uiso 1 1 calc R . . C18 C 0.3466(3) 0.36987(17) 0.74451(15) 0.0270(5) Uani 1 1 d . . . C19 C 0.4703(3) 0.43638(18) 0.82172(16) 0.0303(5) Uani 1 1 d . . . H19A H 0.5201 0.5076 0.8157 0.036 Uiso 1 1 calc R . . C20 C 0.5210(3) 0.39969(19) 0.90670(17) 0.0346(5) Uani 1 1 d . . . H20A H 0.6056 0.4456 0.9589 0.042 Uiso 1 1 calc R . . C21 C 0.4490(3) 0.2963(2) 0.91599(17) 0.0347(5) Uani 1 1 d . . . C22 C 0.3222(3) 0.22970(19) 0.84238(17) 0.0324(5) Uani 1 1 d . . . H22A H 0.2715 0.1592 0.8505 0.039 Uiso 1 1 calc R . . C23 C 0.2670(3) 0.26491(17) 0.75537(16) 0.0280(5) Uani 1 1 d . . . C24 C 0.1312(3) 0.18993(17) 0.67644(17) 0.0312(5) Uani 1 1 d . . . C25 C 0.0121(3) 0.09161(17) 0.70065(16) 0.0307(5) Uani 1 1 d . . . C26 C -0.0852(4) 0.09068(19) 0.78228(18) 0.0373(6) Uani 1 1 d . . . H26A H -0.0677 0.1526 0.8280 0.045 Uiso 1 1 calc R . . C27 C -0.2081(4) -0.0016(2) 0.7961(2) 0.0463(7) Uani 1 1 d . . . H27A H -0.2781 -0.0021 0.8504 0.056 Uiso 1 1 calc R . . C28 C -0.2297(4) -0.0928(2) 0.7319(2) 0.0453(7) Uani 1 1 d . . . H28A H -0.3122 -0.1559 0.7428 0.054 Uiso 1 1 calc R . . C29 C -0.1315(4) -0.0919(2) 0.6521(2) 0.0441(7) Uani 1 1 d . . . H29A H -0.1459 -0.1546 0.6080 0.053 Uiso 1 1 calc R . . C30 C -0.0120(4) -0.00015(19) 0.63599(18) 0.0375(6) Uani 1 1 d . . . H30A H 0.0541 0.0001 0.5802 0.045 Uiso 1 1 calc R . . C31 C 0.5277(9) 0.9426(6) 0.4839(6) 0.054(2) Uani 0.50 1 d P A -1 H31A H 0.6276 0.9145 0.5147 0.065 Uiso 0.50 1 calc PR A -1 Cl3 Cl 0.3144(3) 0.88655(16) 0.52525(14) 0.0655(5) Uani 0.50 1 d P A -1 Cl4 Cl 0.5007(2) 0.90843(13) 0.35459(11) 0.0557(4) Uani 0.50 1 d P A -1 Cl5 Cl 0.5894(5) 1.07740(17) 0.5134(2) 0.0961(9) Uani 0.50 1 d P A -1 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 0.0513(4) 0.0340(3) 0.0301(3) 0.0112(2) 0.0066(3) 0.0188(3) Cl2 0.0566(4) 0.0647(5) 0.0388(4) 0.0194(3) -0.0117(3) 0.0155(4) O1 0.0436(11) 0.0336(10) 0.0467(11) 0.0124(8) -0.0017(8) -0.0054(8) O2 0.0534(11) 0.0336(10) 0.0406(10) 0.0019(8) -0.0133(9) -0.0026(8) O3 0.0490(11) 0.0308(9) 0.0338(9) 0.0083(7) 0.0022(8) 0.0004(8) O4 0.0554(11) 0.0370(10) 0.0273(9) 0.0072(7) -0.0014(8) -0.0009(8) N1 0.0276(10) 0.0224(9) 0.0269(9) 0.0056(7) 0.0006(8) 0.0032(8) N2 0.0283(10) 0.0259(10) 0.0257(9) 0.0034(8) -0.0016(8) 0.0026(8) C1 0.0237(11) 0.0250(11) 0.0289(11) 0.0028(9) 0.0046(9) 0.0082(9) C2 0.0292(12) 0.0262(12) 0.0368(13) 0.0017(10) 0.0044(10) 0.0066(10) C3 0.0316(13) 0.0262(12) 0.0353(13) 0.0016(10) 0.0022(10) 0.0064(10) C4 0.0226(11) 0.0277(11) 0.0262(11) 0.0012(9) 0.0053(9) 0.0076(9) C5 0.0250(11) 0.0276(11) 0.0280(11) 0.0045(9) 0.0042(9) 0.0101(9) C6 0.0336(13) 0.0245(11) 0.0331(12) 0.0045(9) 0.0035(10) 0.0073(10) C7 0.0363(13) 0.0236(11) 0.0379(13) 0.0089(10) 0.0070(10) 0.0086(10) C8 0.0336(13) 0.0304(12) 0.0276(11) 0.0077(9) 0.0059(10) 0.0146(10) C9 0.0295(12) 0.0286(12) 0.0289(12) 0.0049(9) 0.0041(9) 0.0099(10) C10 0.0289(12) 0.0267(11) 0.0279(11) 0.0053(9) 0.0048(9) 0.0104(9) C11 0.0289(12) 0.0276(12) 0.0330(12) 0.0068(10) 0.0004(10) 0.0079(10) C12 0.0340(13) 0.0267(12) 0.0338(12) 0.0063(10) -0.0050(10) 0.0109(10) C13 0.0405(14) 0.0294(12) 0.0362(13) 0.0055(10) -0.0066(11) 0.0125(11) C14 0.0607(18) 0.0416(15) 0.0363(14) 0.0032(11) -0.0026(13) 0.0240(14) C15 0.070(2) 0.0321(14) 0.0458(16) -0.0045(12) -0.0159(15) 0.0208(14) C16 0.0488(16) 0.0259(13) 0.0602(18) 0.0040(12) -0.0155(14) 0.0046(12) C17 0.0387(14) 0.0314(13) 0.0460(15) 0.0084(11) -0.0080(11) 0.0080(11) C18 0.0282(12) 0.0311(12) 0.0234(11) 0.0039(9) 0.0032(9) 0.0112(9) C19 0.0293(12) 0.0302(12) 0.0293(12) 0.0006(9) 0.0015(9) 0.0066(10) C20 0.0291(13) 0.0426(14) 0.0299(12) -0.0007(10) -0.0017(10) 0.0105(11) C21 0.0343(13) 0.0465(15) 0.0271(12) 0.0083(10) 0.0002(10) 0.0177(11) C22 0.0348(13) 0.0332(12) 0.0322(12) 0.0070(10) 0.0019(10) 0.0143(10) C23 0.0290(12) 0.0293(12) 0.0261(11) 0.0033(9) 0.0014(9) 0.0099(9) C24 0.0360(13) 0.0286(12) 0.0291(12) 0.0038(10) 0.0019(10) 0.0101(10) C25 0.0345(13) 0.0270(12) 0.0306(12) 0.0067(9) -0.0021(10) 0.0098(10) C26 0.0503(16) 0.0287(12) 0.0342(13) 0.0077(10) 0.0042(11) 0.0117(11) C27 0.0502(17) 0.0460(16) 0.0450(15) 0.0182(13) 0.0103(13) 0.0102(13) C28 0.0418(15) 0.0302(13) 0.0589(18) 0.0193(12) -0.0108(13) 0.0012(11) C29 0.0489(16) 0.0297(13) 0.0482(16) 0.0021(11) -0.0135(13) 0.0093(12) C30 0.0421(14) 0.0342(13) 0.0352(13) 0.0004(10) -0.0026(11) 0.0134(11) C31 0.031(3) 0.073(5) 0.064(4) 0.023(4) 0.000(3) 0.021(4) Cl3 0.0581(10) 0.0752(13) 0.0791(12) 0.0310(10) 0.0329(9) 0.0290(9) Cl4 0.0529(9) 0.0697(10) 0.0454(8) 0.0135(7) 0.0057(6) 0.0160(7) Cl5 0.132(3) 0.0452(11) 0.0930(18) -0.0014(11) -0.022(2) 0.0094(16) _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 C8 1.743(2) . ? Cl2 C21 1.743(2) . ? O1 C2 1.210(3) . ? O2 C3 1.212(3) . ? O3 C11 1.234(3) . ? O4 C24 1.229(3) . ? N1 C1 1.350(3) . ? N1 C5 1.404(3) . ? N1 H1A 0.8800 . ? N2 C4 1.347(3) . ? N2 C18 1.401(3) . ? N2 H2A 0.8800 . ? C1 C4 1.401(3) . ? C1 C2 1.483(3) . ? C2 C3 1.511(3) . ? C3 C4 1.481(3) . ? C5 C6 1.392(3) . ? C5 C10 1.412(3) . ? C6 C7 1.383(3) . ? C6 H6A 0.9500 . ? C7 C8 1.378(3) . ? C7 H7A 0.9500 . ? C8 C9 1.380(3) . ? C9 C10 1.402(3) . ? C9 H9A 0.9500 . ? C10 C11 1.491(3) . ? C11 C12 1.487(3) . ? C12 C13 1.388(3) . ? C12 C17 1.399(3) . ? C13 C14 1.394(3) . ? C13 H13A 0.9500 . ? C14 C15 1.382(4) . ? C14 H14A 0.9500 . ? C15 C16 1.373(4) . ? C15 H15A 0.9500 . ? C16 C17 1.383(4) . ? C16 H16A 0.9500 . ? C17 H17A 0.9500 . ? C18 C19 1.394(3) . ? C18 C23 1.414(3) . ? C19 C20 1.379(3) . ? C19 H19A 0.9500 . ? C20 C21 1.380(4) . ? C20 H20A 0.9500 . ? C21 C22 1.375(3) . ? C22 C23 1.402(3) . ? C22 H22A 0.9500 . ? C23 C24 1.493(3) . ? C24 C25 1.486(3) . ? C25 C30 1.387(3) . ? C25 C26 1.393(3) . ? C26 C27 1.388(4) . ? C26 H26A 0.9500 . ? C27 C28 1.381(4) . ? C27 H27A 0.9500 . ? C28 C29 1.375(4) . ? C28 H28A 0.9500 . ? C29 C30 1.381(4) . ? C29 H29A 0.9500 . ? C30 H30A 0.9500 . ? C31 Cl5 1.734(8) . ? C31 Cl4 1.759(8) . ? C31 Cl3 1.761(7) . ? C31 H31A 1.0000 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C5 128.57(18) . . ? C1 N1 H1A 115.7 . . ? C5 N1 H1A 115.7 . . ? C4 N2 C18 128.97(19) . . ? C4 N2 H2A 115.5 . . ? C18 N2 H2A 115.5 . . ? N1 C1 C4 129.2(2) . . ? N1 C1 C2 138.7(2) . . ? C4 C1 C2 92.04(18) . . ? O1 C2 C1 138.0(2) . . ? O1 C2 C3 134.1(2) . . ? C1 C2 C3 87.74(17) . . ? O2 C3 C4 138.4(2) . . ? O2 C3 C2 133.7(2) . . ? C4 C3 C2 87.90(17) . . ? N2 C4 C1 128.8(2) . . ? N2 C4 C3 139.1(2) . . ? C1 C4 C3 92.07(18) . . ? C6 C5 N1 121.3(2) . . ? C6 C5 C10 119.5(2) . . ? N1 C5 C10 119.17(19) . . ? C7 C6 C5 120.2(2) . . ? C7 C6 H6A 119.9 . . ? C5 C6 H6A 119.9 . . ? C8 C7 C6 120.4(2) . . ? C8 C7 H7A 119.8 . . ? C6 C7 H7A 119.8 . . ? C7 C8 C9 120.7(2) . . ? C7 C8 Cl1 119.34(17) . . ? C9 C8 Cl1 119.99(18) . . ? C8 C9 C10 120.0(2) . . ? C8 C9 H9A 120.0 . . ? C10 C9 H9A 120.0 . . ? C9 C10 C5 119.1(2) . . ? C9 C10 C11 119.4(2) . . ? C5 C10 C11 121.36(19) . . ? O3 C11 C12 119.0(2) . . ? O3 C11 C10 119.8(2) . . ? C12 C11 C10 121.15(19) . . ? C13 C12 C17 119.6(2) . . ? C13 C12 C11 122.4(2) . . ? C17 C12 C11 117.6(2) . . ? C12 C13 C14 120.0(2) . . ? C12 C13 H13A 120.0 . . ? C14 C13 H13A 120.0 . . ? C15 C14 C13 119.6(3) . . ? C15 C14 H14A 120.2 . . ? C13 C14 H14A 120.2 . . ? C16 C15 C14 120.7(2) . . ? C16 C15 H15A 119.7 . . ? C14 C15 H15A 119.7 . . ? C15 C16 C17 120.3(3) . . ? C15 C16 H16A 119.8 . . ? C17 C16 H16A 119.8 . . ? C16 C17 C12 119.8(3) . . ? C16 C17 H17A 120.1 . . ? C12 C17 H17A 120.1 . . ? C19 C18 N2 122.2(2) . . ? C19 C18 C23 119.5(2) . . ? N2 C18 C23 118.28(19) . . ? C20 C19 C18 120.6(2) . . ? C20 C19 H19A 119.7 . . ? C18 C19 H19A 119.7 . . ? C19 C20 C21 120.0(2) . . ? C19 C20 H20A 120.0 . . ? C21 C20 H20A 120.0 . . ? C22 C21 C20 120.7(2) . . ? C22 C21 Cl2 119.50(19) . . ? C20 C21 Cl2 119.83(19) . . ? C21 C22 C23 120.6(2) . . ? C21 C22 H22A 119.7 . . ? C23 C22 H22A 119.7 . . ? C22 C23 C18 118.6(2) . . ? C22 C23 C24 119.1(2) . . ? C18 C23 C24 122.32(19) . . ? O4 C24 C25 119.0(2) . . ? O4 C24 C23 121.0(2) . . ? C25 C24 C23 120.02(19) . . ? C30 C25 C26 119.5(2) . . ? C30 C25 C24 118.6(2) . . ? C26 C25 C24 121.8(2) . . ? C27 C26 C25 119.3(2) . . ? C27 C26 H26A 120.3 . . ? C25 C26 H26A 120.3 . . ? C28 C27 C26 120.7(3) . . ? C28 C27 H27A 119.6 . . ? C26 C27 H27A 119.6 . . ? C29 C28 C27 119.8(2) . . ? C29 C28 H28A 120.1 . . ? C27 C28 H28A 120.1 . . ? C28 C29 C30 120.2(2) . . ? C28 C29 H29A 119.9 . . ? C30 C29 H29A 119.9 . . ? C29 C30 C25 120.5(3) . . ? C29 C30 H30A 119.8 . . ? C25 C30 H30A 119.8 . . ? Cl5 C31 Cl4 109.0(4) . . ? Cl5 C31 Cl3 111.1(4) . . ? Cl4 C31 Cl3 107.9(4) . . ? Cl5 C31 H31A 109.6 . . ? Cl4 C31 H31A 109.6 . . ? Cl3 C31 H31A 109.6 . . ? 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 C5 N1 C1 C4 179.2(2) . . . . ? C5 N1 C1 C2 -3.8(4) . . . . ? N1 C1 C2 O1 -7.0(5) . . . . ? C4 C1 C2 O1 170.7(3) . . . . ? N1 C1 C2 C3 178.5(3) . . . . ? C4 C1 C2 C3 -3.79(17) . . . . ? O1 C2 C3 O2 8.0(5) . . . . ? C1 C2 C3 O2 -177.1(3) . . . . ? O1 C2 C3 C4 -171.3(3) . . . . ? C1 C2 C3 C4 3.58(16) . . . . ? C18 N2 C4 C1 177.7(2) . . . . ? C18 N2 C4 C3 2.0(4) . . . . ? N1 C1 C4 N2 4.8(4) . . . . ? C2 C1 C4 N2 -173.3(2) . . . . ? N1 C1 C4 C3 -178.1(2) . . . . ? C2 C1 C4 C3 3.86(18) . . . . ? O2 C3 C4 N2 -6.4(5) . . . . ? C2 C3 C4 N2 172.8(3) . . . . ? O2 C3 C4 C1 176.9(3) . . . . ? C2 C3 C4 C1 -3.79(17) . . . . ? C1 N1 C5 C6 -9.3(3) . . . . ? C1 N1 C5 C10 170.0(2) . . . . ? N1 C5 C6 C7 179.3(2) . . . . ? C10 C5 C6 C7 0.0(3) . . . . ? C5 C6 C7 C8 0.9(3) . . . . ? C6 C7 C8 C9 -0.9(4) . . . . ? C6 C7 C8 Cl1 179.40(18) . . . . ? C7 C8 C9 C10 0.0(3) . . . . ? Cl1 C8 C9 C10 179.63(17) . . . . ? C8 C9 C10 C5 1.0(3) . . . . ? C8 C9 C10 C11 178.1(2) . . . . ? C6 C5 C10 C9 -1.0(3) . . . . ? N1 C5 C10 C9 179.71(19) . . . . ? C6 C5 C10 C11 -178.1(2) . . . . ? N1 C5 C10 C11 2.6(3) . . . . ? C9 C10 C11 O3 -152.4(2) . . . . ? C5 C10 C11 O3 24.7(3) . . . . ? C9 C10 C11 C12 28.3(3) . . . . ? C5 C10 C11 C12 -154.6(2) . . . . ? O3 C11 C12 C13 -142.8(2) . . . . ? C10 C11 C12 C13 36.5(3) . . . . ? O3 C11 C12 C17 29.6(3) . . . . ? C10 C11 C12 C17 -151.1(2) . . . . ? C17 C12 C13 C14 -0.6(3) . . . . ? C11 C12 C13 C14 171.7(2) . . . . ? C12 C13 C14 C15 0.8(4) . . . . ? C13 C14 C15 C16 0.1(4) . . . . ? C14 C15 C16 C17 -1.2(4) . . . . ? C15 C16 C17 C12 1.3(4) . . . . ? C13 C12 C17 C16 -0.5(3) . . . . ? C11 C12 C17 C16 -173.1(2) . . . . ? C4 N2 C18 C19 3.1(4) . . . . ? C4 N2 C18 C23 -177.1(2) . . . . ? N2 C18 C19 C20 -177.7(2) . . . . ? C23 C18 C19 C20 2.5(3) . . . . ? C18 C19 C20 C21 -0.1(4) . . . . ? C19 C20 C21 C22 -2.0(4) . . . . ? C19 C20 C21 Cl2 179.52(18) . . . . ? C20 C21 C22 C23 1.6(4) . . . . ? Cl2 C21 C22 C23 -179.92(18) . . . . ? C21 C22 C23 C18 0.9(3) . . . . ? C21 C22 C23 C24 179.1(2) . . . . ? C19 C18 C23 C22 -2.9(3) . . . . ? N2 C18 C23 C22 177.4(2) . . . . ? C19 C18 C23 C24 178.9(2) . . . . ? N2 C18 C23 C24 -0.8(3) . . . . ? C22 C23 C24 O4 -160.6(2) . . . . ? C18 C23 C24 O4 17.6(3) . . . . ? C22 C23 C24 C25 19.2(3) . . . . ? C18 C23 C24 C25 -162.6(2) . . . . ? O4 C24 C25 C30 42.9(3) . . . . ? C23 C24 C25 C30 -136.9(2) . . . . ? O4 C24 C25 C26 -132.6(2) . . . . ? C23 C24 C25 C26 47.6(3) . . . . ? C30 C25 C26 C27 -1.5(4) . . . . ? C24 C25 C26 C27 173.9(2) . . . . ? C25 C26 C27 C28 2.2(4) . . . . ? C26 C27 C28 C29 -1.3(4) . . . . ? C27 C28 C29 C30 -0.2(4) . . . . ? C28 C29 C30 C25 0.9(4) . . . . ? C26 C25 C30 C29 0.0(4) . . . . ? C24 C25 C30 C29 -175.6(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A O3 0.88 1.94 2.645(2) 135.8 . N2 H2A O4 0.88 1.91 2.625(2) 136.6 . C31 H31A O1 1.00 2.74 3.298(8) 115.5 . _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.611 _refine_diff_density_min -0.354 _refine_diff_density_rms 0.069