# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2014 data_a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H28 Cl3 N7 O6' _chemical_formula_weight 640.90 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 orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 17.004(3) _cell_length_b 18.042(4) _cell_length_c 19.082(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5854(2) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 14873 _cell_measurement_theta_min 1.1975 _cell_measurement_theta_max 27.4409 _exptl_crystal_description rod _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.36 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.454 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2656 _exptl_absorpt_coefficient_mu 0.367 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5470 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'CrystalClear (Rigaku Inc., 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Saturn724+ CCD' _diffrn_measurement_method '\w scans at fixed \c = 45\%' _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22071 _diffrn_reflns_av_R_equivalents 0.0566 _diffrn_reflns_av_sigmaI/netI 0.0470 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.40 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5158 _reflns_number_gt 4739 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution 'SHELX-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELX-97 (Sheldrick, 2008)' _computing_molecular_graphics ; Mercury: visualization and analysis of crystal structures, C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor, M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006. ; _computing_publication_material 'SHELX-97 (Sheldrick, 2008)' _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^)+(0.1031P)^2^+17.9998P] 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 5158 _refine_ls_number_parameters 383 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1244 _refine_ls_R_factor_gt 0.1154 _refine_ls_wR_factor_ref 0.2836 _refine_ls_wR_factor_gt 0.2773 _refine_ls_goodness_of_fit_ref 1.262 _refine_ls_restrained_S_all 1.262 _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 -0.22571(13) -0.09029(11) 0.37564(14) 0.0796(7) Uani 1 1 d . . . Cl2 Cl -0.01759(13) 0.40228(11) 0.00762(9) 0.0667(6) Uani 1 1 d . . . Cl3 Cl 0.36768(9) 0.19330(10) 0.36820(8) 0.0480(4) Uani 1 1 d . . . O1 O -0.0013(3) 0.0213(2) 0.2623(2) 0.0476(11) Uani 1 1 d . . . O2 O 0.1214(3) 0.2394(3) 0.1640(2) 0.0509(12) Uani 1 1 d . . . O3 O -0.0865(2) 0.3734(2) 0.2507(2) 0.0413(10) Uani 1 1 d . . . O4 O -0.1670(3) 0.1671(2) 0.3944(2) 0.0505(12) Uani 1 1 d . . . O5 O 0.2679(3) 0.0725(3) 0.3025(3) 0.0760(17) Uani 1 1 d . . . H5 H 0.2943 0.1094 0.3153 0.091 Uiso 1 1 d R . . O6 O -0.0861(3) 0.3941(2) 0.4973(2) 0.0533(12) Uani 1 1 d . . . H6 H -0.0971 0.3663 0.5311 0.064 Uiso 1 1 d R . . N1 N -0.1082(3) -0.0272(3) 0.3119(3) 0.0538(15) Uani 1 1 d . . . N2 N -0.1926(3) 0.0487(3) 0.3798(3) 0.0549(15) Uani 1 1 d . . . N3 N -0.0778(3) 0.1010(3) 0.3282(3) 0.0383(11) Uani 1 1 d . . . N4 N 0.0536(3) 0.3143(3) 0.0931(3) 0.0468(13) Uani 1 1 d . . . N5 N 0.0175(3) 0.3020(3) 0.2137(3) 0.0383(11) Uani 1 1 d . . . N6 N -0.0531(3) 0.3832(3) 0.1382(3) 0.0418(12) Uani 1 1 d . . . N7 N 0.6740(3) 0.1281(3) 0.5698(3) 0.0498(14) Uani 1 1 d . . . C1 C -0.1689(4) -0.0146(4) 0.3527(4) 0.0582(19) Uani 1 1 d . . . C2 C -0.0641(3) 0.0340(3) 0.3017(3) 0.0411(14) Uani 1 1 d . . . C3 C -0.1435(4) 0.1040(3) 0.3647(3) 0.0438(15) Uani 1 1 d . . . C4 C 0.0610(4) 0.0731(3) 0.2580(3) 0.0432(15) Uani 1 1 d . . . C5 C 0.1307(4) 0.0517(4) 0.2869(4) 0.0521(17) Uani 1 1 d . . . H5A H 0.1341 0.0068 0.3127 0.062 Uiso 1 1 calc R . . C6 C 0.1969(4) 0.0963(4) 0.2783(4) 0.0516(17) Uani 1 1 d . . . C7 C 0.1901(4) 0.1618(3) 0.2408(4) 0.0473(16) Uani 1 1 d . . . H7 H 0.2341 0.1937 0.2357 0.057 Uiso 1 1 calc R . . C8 C 0.1197(4) 0.1800(3) 0.2113(3) 0.0414(14) Uani 1 1 d . . . C9 C 0.0530(4) 0.1361(3) 0.2182(3) 0.0422(14) Uani 1 1 d . . . H9 H 0.0045 0.1490 0.1966 0.051 Uiso 1 1 calc R . . C10 C 0.0607(4) 0.2862(3) 0.1582(3) 0.0425(14) Uani 1 1 d . . . C11 C -0.0047(4) 0.3624(3) 0.0891(3) 0.0441(15) Uani 1 1 d . . . C12 C -0.0386(3) 0.3503(3) 0.1997(3) 0.0332(12) Uani 1 1 d . . . C13 C -0.0909(3) 0.3365(3) 0.3158(3) 0.0367(13) Uani 1 1 d . . . C14 C -0.0803(4) 0.3806(3) 0.3740(3) 0.0401(14) Uani 1 1 d . . . H14 H -0.0628 0.4303 0.3695 0.048 Uiso 1 1 calc R . . C15 C -0.0959(3) 0.3499(3) 0.4400(3) 0.0406(14) Uani 1 1 d . . . C16 C -0.1213(4) 0.2772(3) 0.4453(3) 0.0413(14) Uani 1 1 d . . . H16 H -0.1324 0.2559 0.4897 0.050 Uiso 1 1 calc R . . C17 C -0.1302(4) 0.2362(3) 0.3841(3) 0.0411(14) Uani 1 1 d . . . C18 C -0.1153(3) 0.2638(3) 0.3177(3) 0.0361(13) Uani 1 1 d . . . H18 H -0.1214 0.2348 0.2766 0.043 Uiso 1 1 calc R . . C19 C 0.7540(5) 0.0997(5) 0.5450(4) 0.071(2) Uani 1 1 d . . . H19A H 0.7622 0.1166 0.4962 0.085 Uiso 1 1 calc R . . H19B H 0.7953 0.1229 0.5742 0.085 Uiso 1 1 calc R . . C20 C 0.7656(6) 0.0159(6) 0.5472(5) 0.086(3) Uani 1 1 d . . . H20A H 0.7252 -0.0082 0.5184 0.128 Uiso 1 1 calc R . . H20C H 0.7611 -0.0015 0.5957 0.128 Uiso 1 1 calc R . . H20B H 0.8178 0.0035 0.5289 0.128 Uiso 1 1 calc R . . C21 C 0.6750(5) 0.2097(5) 0.5583(5) 0.075(2) Uani 1 1 d . . . H21A H 0.6793 0.2193 0.5074 0.091 Uiso 1 1 calc R . . H21B H 0.7225 0.2304 0.5810 0.091 Uiso 1 1 calc R . . C22 C 0.6026(6) 0.2514(5) 0.5865(5) 0.082(3) Uani 1 1 d . . . H22A H 0.5549 0.2312 0.5648 0.123 Uiso 1 1 calc R . . H22B H 0.6072 0.3042 0.5751 0.123 Uiso 1 1 calc R . . H22C H 0.5996 0.2453 0.6374 0.123 Uiso 1 1 calc R . . C23 C 0.6634(5) 0.1102(5) 0.6474(4) 0.067(2) Uani 1 1 d . . . H23A H 0.6116 0.1293 0.6628 0.081 Uiso 1 1 calc R . . H23B H 0.6627 0.0557 0.6532 0.081 Uiso 1 1 calc R . . C24 C 0.7261(5) 0.1420(6) 0.6944(4) 0.077(2) Uani 1 1 d . . . H24B H 0.7762 0.1171 0.6851 0.116 Uiso 1 1 calc R . . H24C H 0.7112 0.1344 0.7435 0.116 Uiso 1 1 calc R . . H24A H 0.7316 0.1952 0.6852 0.116 Uiso 1 1 calc R . . C25 C 0.6092(5) 0.0893(5) 0.5329(4) 0.067(2) Uani 1 1 d . . . H25A H 0.5585 0.1081 0.5511 0.080 Uiso 1 1 calc R . . H25B H 0.6122 0.0358 0.5443 0.080 Uiso 1 1 calc R . . C26 C 0.6094(5) 0.0978(6) 0.4536(4) 0.076(2) Uani 1 1 d . . . H26A H 0.5641 0.0715 0.4338 0.113 Uiso 1 1 calc R . . H26C H 0.6580 0.0768 0.4344 0.113 Uiso 1 1 calc R . . H26B H 0.6061 0.1504 0.4414 0.113 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 0.0683(13) 0.0558(12) 0.1145(18) -0.0106(11) 0.0254(12) -0.0224(10) Cl2 0.0927(15) 0.0639(11) 0.0435(10) 0.0149(8) 0.0025(9) 0.0094(10) Cl3 0.0451(9) 0.0596(10) 0.0393(8) 0.0005(7) 0.0000(7) -0.0053(7) O1 0.042(2) 0.034(2) 0.066(3) -0.005(2) 0.005(2) -0.0031(19) O2 0.044(3) 0.053(3) 0.056(3) 0.013(2) 0.017(2) 0.007(2) O3 0.045(2) 0.037(2) 0.041(2) 0.0049(18) 0.0052(19) 0.0066(19) O4 0.064(3) 0.036(2) 0.051(3) -0.0001(19) 0.018(2) -0.009(2) O5 0.051(3) 0.049(3) 0.128(5) 0.014(3) -0.033(3) -0.001(2) O6 0.072(3) 0.048(3) 0.040(2) -0.009(2) 0.006(2) -0.006(2) N1 0.044(3) 0.040(3) 0.077(4) -0.006(3) 0.004(3) -0.006(3) N2 0.047(3) 0.046(3) 0.071(4) -0.002(3) 0.014(3) -0.007(3) N3 0.038(3) 0.034(3) 0.042(3) 0.001(2) 0.002(2) -0.005(2) N4 0.054(3) 0.047(3) 0.039(3) 0.006(2) 0.009(2) -0.002(3) N5 0.036(3) 0.041(3) 0.039(3) 0.002(2) 0.005(2) -0.001(2) N6 0.045(3) 0.037(3) 0.043(3) 0.006(2) 0.001(2) -0.002(2) N7 0.045(3) 0.060(4) 0.044(3) 0.004(3) 0.000(2) -0.008(3) C1 0.052(4) 0.044(4) 0.079(5) -0.005(3) 0.007(4) -0.010(3) C2 0.035(3) 0.036(3) 0.053(4) -0.001(3) -0.007(3) 0.001(3) C3 0.053(4) 0.036(3) 0.043(3) -0.002(3) 0.004(3) -0.004(3) C4 0.035(3) 0.038(3) 0.057(4) -0.008(3) 0.002(3) -0.006(3) C5 0.053(4) 0.033(3) 0.070(4) 0.011(3) -0.011(3) -0.004(3) C6 0.045(4) 0.040(3) 0.070(5) -0.003(3) -0.017(3) 0.003(3) C7 0.032(3) 0.038(3) 0.072(4) -0.006(3) -0.004(3) -0.003(3) C8 0.042(4) 0.038(3) 0.044(3) -0.003(3) 0.007(3) 0.004(3) C9 0.036(3) 0.047(3) 0.044(3) -0.004(3) -0.001(3) 0.003(3) C10 0.040(3) 0.038(3) 0.049(4) 0.002(3) 0.005(3) -0.002(3) C11 0.057(4) 0.036(3) 0.040(3) 0.005(3) -0.001(3) -0.005(3) C12 0.037(3) 0.028(3) 0.035(3) 0.000(2) -0.004(2) -0.005(2) C13 0.027(3) 0.045(3) 0.038(3) 0.004(3) 0.004(2) 0.006(2) C14 0.041(3) 0.036(3) 0.043(3) -0.002(3) 0.005(3) 0.001(3) C15 0.036(3) 0.044(3) 0.042(3) -0.007(3) 0.002(3) 0.005(3) C16 0.046(4) 0.043(3) 0.035(3) 0.000(3) 0.006(3) 0.004(3) C17 0.043(4) 0.032(3) 0.049(3) 0.002(3) 0.005(3) 0.003(3) C18 0.031(3) 0.039(3) 0.038(3) -0.004(2) 0.004(2) 0.000(2) C19 0.054(5) 0.085(6) 0.073(5) 0.010(4) 0.008(4) 0.002(4) C20 0.075(6) 0.101(7) 0.081(6) 0.007(5) 0.000(5) 0.017(5) C21 0.079(6) 0.073(5) 0.074(5) 0.013(4) -0.009(5) -0.012(5) C22 0.090(6) 0.064(5) 0.093(7) 0.006(5) -0.025(5) 0.012(5) C23 0.062(5) 0.071(5) 0.070(5) 0.004(4) 0.001(4) 0.001(4) C24 0.074(6) 0.097(7) 0.061(5) -0.007(5) -0.018(4) -0.001(5) C25 0.057(5) 0.082(6) 0.061(5) -0.004(4) -0.005(4) -0.003(4) C26 0.073(6) 0.104(7) 0.050(4) -0.001(4) -0.009(4) 0.003(5) _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 1.730(7) . ? Cl2 C11 1.728(6) . ? O1 C2 1.326(7) . ? O1 C4 1.417(7) . ? O2 C10 1.338(7) . ? O2 C8 1.400(7) . ? O3 C12 1.336(7) . ? O3 C13 1.411(7) . ? O4 C3 1.333(7) . ? O4 C17 1.408(7) . ? O5 C6 1.361(8) . ? O5 H5 0.8401 . ? O6 C15 1.363(7) . ? O6 H6 0.8401 . ? N1 C1 1.312(9) . ? N1 C2 1.348(8) . ? N2 C1 1.317(9) . ? N2 C3 1.333(8) . ? N3 C3 1.318(8) . ? N3 C2 1.330(8) . ? N4 C11 1.321(8) . ? N4 C10 1.346(8) . ? N5 C12 1.320(7) . ? N5 C10 1.321(8) . ? N6 C11 1.301(8) . ? N6 C12 1.339(7) . ? N7 C25 1.483(9) . ? N7 C21 1.490(10) . ? N7 C23 1.526(10) . ? N7 C19 1.529(10) . ? C4 C5 1.364(9) . ? C4 C9 1.374(9) . ? C5 C6 1.393(9) . ? C5 H5A 0.9500 . ? C6 C7 1.386(9) . ? C7 C8 1.362(9) . ? C7 H7 0.9500 . ? C8 C9 1.391(9) . ? C9 H9 0.9500 . ? C13 C18 1.376(8) . ? C13 C14 1.376(8) . ? C14 C15 1.402(8) . ? C14 H14 0.9500 . ? C15 C16 1.383(9) . ? C16 C17 1.392(8) . ? C16 H16 0.9500 . ? C17 C18 1.385(8) . ? C18 H18 0.9500 . ? C19 C20 1.524(12) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 H20A 0.9800 . ? C20 H20C 0.9800 . ? C20 H20B 0.9800 . ? C21 C22 1.539(12) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 C24 1.507(11) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C24 H24A 0.9800 . ? C25 C26 1.521(11) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 H26A 0.9800 . ? C26 H26C 0.9800 . ? C26 H26B 0.9800 . ? 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 C2 O1 C4 121.4(5) . . ? C10 O2 C8 121.4(5) . . ? C12 O3 C13 121.8(4) . . ? C3 O4 C17 124.2(5) . . ? C6 O5 H5 108.8 . . ? C15 O6 H6 103.8 . . ? C1 N1 C2 112.4(6) . . ? C1 N2 C3 111.8(6) . . ? C3 N3 C2 112.7(5) . . ? C11 N4 C10 111.6(5) . . ? C12 N5 C10 112.4(5) . . ? C11 N6 C12 112.7(5) . . ? C25 N7 C21 113.9(6) . . ? C25 N7 C23 105.9(6) . . ? C21 N7 C23 110.6(6) . . ? C25 N7 C19 110.8(6) . . ? C21 N7 C19 106.0(6) . . ? C23 N7 C19 109.6(6) . . ? N1 C1 N2 128.7(6) . . ? N1 C1 Cl1 116.9(5) . . ? N2 C1 Cl1 114.5(5) . . ? O1 C2 N3 120.9(5) . . ? O1 C2 N1 112.8(5) . . ? N3 C2 N1 126.3(6) . . ? N3 C3 N2 127.9(6) . . ? N3 C3 O4 121.0(5) . . ? N2 C3 O4 111.0(6) . . ? C5 C4 C9 123.0(6) . . ? C5 C4 O1 116.1(5) . . ? C9 C4 O1 120.3(6) . . ? C4 C5 C6 119.5(6) . . ? C4 C5 H5A 120.3 . . ? C6 C5 H5A 120.3 . . ? O5 C6 C7 121.2(6) . . ? O5 C6 C5 119.6(6) . . ? C7 C6 C5 119.0(6) . . ? C8 C7 C6 119.6(6) . . ? C8 C7 H7 120.2 . . ? C6 C7 H7 120.2 . . ? C7 C8 C9 122.7(6) . . ? C7 C8 O2 115.7(6) . . ? C9 C8 O2 120.9(6) . . ? C4 C9 C8 116.3(6) . . ? C4 C9 H9 121.9 . . ? C8 C9 H9 121.9 . . ? N5 C10 O2 119.8(6) . . ? N5 C10 N4 127.5(6) . . ? O2 C10 N4 112.6(5) . . ? N6 C11 N4 128.5(6) . . ? N6 C11 Cl2 116.6(5) . . ? N4 C11 Cl2 114.9(5) . . ? N5 C12 O3 119.9(5) . . ? N5 C12 N6 127.1(5) . . ? O3 C12 N6 112.9(5) . . ? C18 C13 C14 124.7(5) . . ? C18 C13 O3 119.2(5) . . ? C14 C13 O3 115.5(5) . . ? C13 C14 C15 118.1(6) . . ? C13 C14 H14 120.9 . . ? C15 C14 H14 120.9 . . ? O6 C15 C16 122.3(6) . . ? O6 C15 C14 117.7(5) . . ? C16 C15 C14 120.0(5) . . ? C15 C16 C17 118.5(6) . . ? C15 C16 H16 120.8 . . ? C17 C16 H16 120.8 . . ? C18 C17 C16 123.8(5) . . ? C18 C17 O4 121.9(5) . . ? C16 C17 O4 113.7(5) . . ? C13 C18 C17 115.0(5) . . ? C13 C18 H18 122.5 . . ? C17 C18 H18 122.5 . . ? C20 C19 N7 116.0(7) . . ? C20 C19 H19A 108.3 . . ? N7 C19 H19A 108.3 . . ? C20 C19 H19B 108.3 . . ? N7 C19 H19B 108.3 . . ? H19A C19 H19B 107.4 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? H20C C20 H20B 109.5 . . ? N7 C21 C22 115.0(7) . . ? N7 C21 H21A 108.5 . . ? C22 C21 H21A 108.5 . . ? N7 C21 H21B 108.5 . . ? C22 C21 H21B 108.5 . . ? H21A C21 H21B 107.5 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C24 C23 N7 114.5(7) . . ? C24 C23 H23A 108.6 . . ? N7 C23 H23A 108.6 . . ? C24 C23 H23B 108.6 . . ? N7 C23 H23B 108.6 . . ? H23A C23 H23B 107.6 . . ? C23 C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C23 C24 H24A 109.5 . . ? H24B C24 H24A 109.5 . . ? H24C C24 H24A 109.5 . . ? N7 C25 C26 115.1(7) . . ? N7 C25 H25A 108.5 . . ? C26 C25 H25A 108.5 . . ? N7 C25 H25B 108.5 . . ? C26 C25 H25B 108.5 . . ? H25A C25 H25B 107.5 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? H26C C26 H26B 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 C2 N1 C1 N2 4.2(12) . . . . ? C2 N1 C1 Cl1 -175.0(5) . . . . ? C3 N2 C1 N1 -3.8(12) . . . . ? C3 N2 C1 Cl1 175.4(5) . . . . ? C4 O1 C2 N3 12.6(9) . . . . ? C4 O1 C2 N1 -165.9(6) . . . . ? C3 N3 C2 O1 178.6(5) . . . . ? C3 N3 C2 N1 -3.1(9) . . . . ? C1 N1 C2 O1 178.1(6) . . . . ? C1 N1 C2 N3 -0.3(10) . . . . ? C2 N3 C3 N2 3.6(10) . . . . ? C2 N3 C3 O4 -179.2(6) . . . . ? C1 N2 C3 N3 -0.6(11) . . . . ? C1 N2 C3 O4 -178.0(6) . . . . ? C17 O4 C3 N3 6.9(10) . . . . ? C17 O4 C3 N2 -175.5(6) . . . . ? C2 O1 C4 C5 112.2(7) . . . . ? C2 O1 C4 C9 -76.5(8) . . . . ? C9 C4 C5 C6 2.3(11) . . . . ? O1 C4 C5 C6 173.3(6) . . . . ? C4 C5 C6 O5 -175.0(7) . . . . ? C4 C5 C6 C7 0.4(11) . . . . ? O5 C6 C7 C8 173.2(6) . . . . ? C5 C6 C7 C8 -2.1(10) . . . . ? C6 C7 C8 C9 1.3(10) . . . . ? C6 C7 C8 O2 -168.7(6) . . . . ? C10 O2 C8 C7 -146.0(6) . . . . ? C10 O2 C8 C9 43.7(8) . . . . ? C5 C4 C9 C8 -3.0(9) . . . . ? O1 C4 C9 C8 -173.7(5) . . . . ? C7 C8 C9 C4 1.2(9) . . . . ? O2 C8 C9 C4 170.7(5) . . . . ? C12 N5 C10 O2 178.4(5) . . . . ? C12 N5 C10 N4 1.3(9) . . . . ? C8 O2 C10 N5 32.8(9) . . . . ? C8 O2 C10 N4 -149.7(6) . . . . ? C11 N4 C10 N5 -0.3(9) . . . . ? C11 N4 C10 O2 -177.6(5) . . . . ? C12 N6 C11 N4 0.7(9) . . . . ? C12 N6 C11 Cl2 -179.4(4) . . . . ? C10 N4 C11 N6 -0.8(10) . . . . ? C10 N4 C11 Cl2 179.3(4) . . . . ? C10 N5 C12 O3 -178.6(5) . . . . ? C10 N5 C12 N6 -1.4(8) . . . . ? C13 O3 C12 N5 -14.2(8) . . . . ? C13 O3 C12 N6 168.3(5) . . . . ? C11 N6 C12 N5 0.5(9) . . . . ? C11 N6 C12 O3 177.9(5) . . . . ? C12 O3 C13 C18 -61.7(7) . . . . ? C12 O3 C13 C14 126.9(6) . . . . ? C18 C13 C14 C15 -0.6(9) . . . . ? O3 C13 C14 C15 170.3(5) . . . . ? C13 C14 C15 O6 -179.3(5) . . . . ? C13 C14 C15 C16 0.0(9) . . . . ? O6 C15 C16 C17 179.6(6) . . . . ? C14 C15 C16 C17 0.4(9) . . . . ? C15 C16 C17 C18 -0.2(10) . . . . ? C15 C16 C17 O4 -171.2(5) . . . . ? C3 O4 C17 C18 51.9(9) . . . . ? C3 O4 C17 C16 -136.9(6) . . . . ? C14 C13 C18 C17 0.8(9) . . . . ? O3 C13 C18 C17 -169.8(5) . . . . ? C16 C17 C18 C13 -0.4(9) . . . . ? O4 C17 C18 C13 169.9(5) . . . . ? C25 N7 C19 C20 -52.2(9) . . . . ? C21 N7 C19 C20 -176.3(8) . . . . ? C23 N7 C19 C20 64.3(9) . . . . ? C25 N7 C21 C22 63.6(9) . . . . ? C23 N7 C21 C22 -55.6(9) . . . . ? C19 N7 C21 C22 -174.3(7) . . . . ? C25 N7 C23 C24 177.4(7) . . . . ? C21 N7 C23 C24 -58.7(9) . . . . ? C19 N7 C23 C24 57.9(9) . . . . ? C21 N7 C25 C26 59.7(9) . . . . ? C23 N7 C25 C26 -178.5(7) . . . . ? C19 N7 C25 C26 -59.8(9) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.244 _refine_diff_density_min -0.648 _refine_diff_density_rms 0.095 _database_code_depnum_ccdc_archive 'CCDC 968607' data_a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H28 Br Cl2 N7 O6' _chemical_formula_weight 685.36 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' Br Br -0.2901 2.4595 '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' 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 orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 17.077(3) _cell_length_b 17.927(4) _cell_length_c 19.393(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5937(2) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 13905 _cell_measurement_theta_min 1.5469 _cell_measurement_theta_max 27.4802 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.534 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2800 _exptl_absorpt_coefficient_mu 1.618 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6977 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'CrystalClear (Rigaku Inc., 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Saturn724+ CCD' _diffrn_measurement_method '\w scans at fixed \c = 45\%' _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18245 _diffrn_reflns_av_R_equivalents 0.1047 _diffrn_reflns_av_sigmaI/netI 0.0997 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5221 _reflns_number_gt 4079 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution 'SHELX-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELX-97 (Sheldrick, 2008)' _computing_molecular_graphics ; Mercury: visualization and analysis of crystal structures, C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor, M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006. ; _computing_publication_material 'SHELX-97 (Sheldrick, 2008)' _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^)+(0.0368P)^2^+57.6565P] 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 5221 _refine_ls_number_parameters 383 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1808 _refine_ls_R_factor_gt 0.1483 _refine_ls_wR_factor_ref 0.2570 _refine_ls_wR_factor_gt 0.2404 _refine_ls_goodness_of_fit_ref 1.300 _refine_ls_restrained_S_all 1.300 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.001 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 0.2278(2) 0.58909(19) 0.3722(2) 0.0703(11) Uani 1 1 d . . . Cl2 Cl 0.0122(2) 0.09898(19) 0.00809(16) 0.0654(11) Uani 1 1 d . . . O1 O 0.0030(5) 0.4798(4) 0.2615(4) 0.043(2) Uani 1 1 d . . . O2 O -0.1236(5) 0.2629(4) 0.1647(4) 0.047(2) Uani 1 1 d . . . O3 O 0.0855(4) 0.1278(4) 0.2459(4) 0.0361(18) Uani 1 1 d . . . O4 O 0.1647(5) 0.3300(4) 0.3923(4) 0.042(2) Uani 1 1 d . . . O5 O -0.2657(5) 0.4340(4) 0.3006(5) 0.071(3) Uani 1 1 d . . . H5 H -0.2970 0.4047 0.3202 0.085 Uiso 1 1 d R . . O6 O 0.0843(5) 0.1006(4) 0.4878(4) 0.048(2) Uani 1 1 d . . . H6 H 0.0595 0.1243 0.5182 0.057 Uiso 1 1 d R . . N1 N 0.1093(6) 0.5266(5) 0.3111(6) 0.047(3) Uani 1 1 d . . . N2 N 0.0778(5) 0.3989(4) 0.3270(4) 0.031(2) Uani 1 1 d . . . N3 N 0.1926(6) 0.4503(5) 0.3784(5) 0.049(3) Uani 1 1 d . . . N4 N -0.0190(6) 0.1987(5) 0.2119(4) 0.036(2) Uani 1 1 d . . . N5 N -0.0573(6) 0.1866(5) 0.0938(4) 0.042(2) Uani 1 1 d . . . N6 N 0.0502(5) 0.1173(5) 0.1365(4) 0.034(2) Uani 1 1 d . . . C1 C 0.1682(8) 0.5142(7) 0.3505(7) 0.052(3) Uani 1 1 d . . . C2 C 0.0647(7) 0.4659(7) 0.3013(6) 0.044(3) Uani 1 1 d . . . C3 C 0.1426(7) 0.3950(6) 0.3633(5) 0.036(3) Uani 1 1 d . . . C4 C 0.1282(6) 0.2620(5) 0.3809(6) 0.035(3) Uani 1 1 d . . . C5 C 0.1182(6) 0.2184(6) 0.4394(5) 0.035(3) Uani 1 1 d . . . H5A H 0.1288 0.2381 0.4839 0.042 Uiso 1 1 calc R . . C6 C 0.0925(7) 0.1453(6) 0.4318(6) 0.040(3) Uani 1 1 d . . . C7 C 0.0779(6) 0.1175(6) 0.3672(5) 0.034(2) Uani 1 1 d . . . H7 H 0.0606 0.0675 0.3612 0.040 Uiso 1 1 calc R . . C8 C 0.0890(6) 0.1642(6) 0.3104(5) 0.027(2) Uani 1 1 d . . . C9 C 0.1138(5) 0.2355(5) 0.3153(6) 0.029(2) Uani 1 1 d . . . H9 H 0.1210 0.2659 0.2757 0.035 Uiso 1 1 calc R . . C10 C 0.0360(6) 0.1495(5) 0.1972(5) 0.031(2) Uani 1 1 d . . . C11 C 0.0007(7) 0.1390(6) 0.0886(6) 0.039(3) Uani 1 1 d . . . C12 C -0.0635(7) 0.2156(5) 0.1572(6) 0.037(3) Uani 1 1 d . . . C13 C -0.1201(6) 0.3230(6) 0.2111(5) 0.034(3) Uani 1 1 d . . . C14 C -0.1908(7) 0.3414(6) 0.2397(6) 0.045(3) Uani 1 1 d . . . H14 H -0.2353 0.3102 0.2341 0.054 Uiso 1 1 calc R . . C15 C -0.1954(7) 0.4072(6) 0.2774(7) 0.045(3) Uani 1 1 d . . . C16 C -0.1292(8) 0.4509(6) 0.2874(6) 0.049(3) Uani 1 1 d . . . H16 H -0.1316 0.4951 0.3144 0.058 Uiso 1 1 calc R . . C17 C -0.0599(6) 0.4287(5) 0.2571(6) 0.034(3) Uani 1 1 d . . . C18 C -0.0531(6) 0.3645(6) 0.2184(5) 0.036(3) Uani 1 1 d . . . H18 H -0.0049 0.3500 0.1979 0.043 Uiso 1 1 calc R . . N13 N 0.3244(6) 0.1282(5) 0.0694(5) 0.046(3) Uani 1 1 d . . . C37 C 0.3341(8) 0.1088(7) 0.1433(6) 0.057(4) Uani 1 1 d . . . H37B H 0.3867 0.1251 0.1585 0.069 Uiso 1 1 calc R . . H37A H 0.3317 0.0539 0.1481 0.069 Uiso 1 1 calc R . . C38 C 0.2740(8) 0.1430(8) 0.1903(7) 0.070(4) Uani 1 1 d . . . H38A H 0.2215 0.1268 0.1762 0.105 Uiso 1 1 calc R . . H38B H 0.2773 0.1975 0.1875 0.105 Uiso 1 1 calc R . . H38C H 0.2838 0.1270 0.2378 0.105 Uiso 1 1 calc R . . C39 C 0.3893(8) 0.0889(8) 0.0335(6) 0.059(4) Uani 1 1 d . . . H39A H 0.3858 0.0351 0.0444 0.071 Uiso 1 1 calc R . . H39B H 0.4396 0.1073 0.0524 0.071 Uiso 1 1 calc R . . C40 C 0.3912(9) 0.0980(9) -0.0458(7) 0.075(5) Uani 1 1 d . . . H40C H 0.4355 0.0699 -0.0646 0.113 Uiso 1 1 calc R . . H40B H 0.3969 0.1509 -0.0574 0.113 Uiso 1 1 calc R . . H40A H 0.3423 0.0788 -0.0654 0.113 Uiso 1 1 calc R . . C41 C 0.3272(8) 0.2105(7) 0.0582(6) 0.056(4) Uani 1 1 d . . . H41A H 0.2798 0.2327 0.0792 0.067 Uiso 1 1 calc R . . H41B H 0.3245 0.2200 0.0079 0.067 Uiso 1 1 calc R . . C42 C 0.3980(9) 0.2508(8) 0.0864(8) 0.080(5) Uani 1 1 d . . . H42B H 0.4454 0.2322 0.0637 0.120 Uiso 1 1 calc R . . H42A H 0.4018 0.2420 0.1362 0.120 Uiso 1 1 calc R . . H42C H 0.3927 0.3045 0.0778 0.120 Uiso 1 1 calc R . . C43 C 0.2454(9) 0.1027(8) 0.0438(7) 0.065(4) Uani 1 1 d . . . H43B H 0.2391 0.1198 -0.0044 0.078 Uiso 1 1 calc R . . H43A H 0.2045 0.1276 0.0717 0.078 Uiso 1 1 calc R . . C44 C 0.2307(9) 0.0191(8) 0.0460(7) 0.074(5) Uani 1 1 d . . . H44C H 0.2703 -0.0066 0.0181 0.112 Uiso 1 1 calc R . . H44A H 0.1785 0.0084 0.0275 0.112 Uiso 1 1 calc R . . H44B H 0.2338 0.0015 0.0938 0.112 Uiso 1 1 calc R . . Br1 Br 0.13206(7) 0.30970(7) 0.12685(6) 0.0456(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 Cl1 0.060(2) 0.055(2) 0.095(3) 0.015(2) -0.025(2) -0.0248(17) Cl2 0.096(3) 0.061(2) 0.0389(17) -0.0166(16) -0.0080(18) 0.012(2) O1 0.040(5) 0.032(4) 0.058(5) 0.002(4) -0.006(4) -0.007(4) O2 0.048(5) 0.046(5) 0.047(5) -0.014(4) -0.023(4) 0.010(4) O3 0.038(5) 0.038(4) 0.033(4) -0.004(3) -0.004(4) 0.005(4) O4 0.047(5) 0.040(4) 0.037(4) 0.008(3) -0.017(4) -0.008(4) O5 0.050(6) 0.044(5) 0.119(8) -0.019(5) 0.042(6) -0.003(5) O6 0.060(6) 0.043(5) 0.041(5) 0.009(4) 0.006(4) 0.002(4) N1 0.028(6) 0.048(6) 0.066(7) 0.011(5) -0.001(5) -0.006(5) N2 0.033(6) 0.029(5) 0.031(5) 0.004(4) -0.001(4) -0.003(4) N3 0.048(7) 0.045(6) 0.054(6) 0.001(5) -0.003(5) -0.009(5) N4 0.045(6) 0.032(5) 0.031(5) 0.000(4) -0.007(4) -0.001(5) N5 0.057(7) 0.037(5) 0.032(5) 0.003(5) -0.011(5) -0.002(5) N6 0.036(6) 0.037(5) 0.029(5) 0.000(4) 0.003(4) -0.001(4) C1 0.037(8) 0.043(7) 0.075(9) 0.006(7) -0.011(7) -0.015(6) C2 0.027(7) 0.052(7) 0.051(7) -0.005(6) -0.004(6) 0.005(6) C3 0.037(7) 0.041(6) 0.030(6) -0.006(5) -0.005(5) 0.000(5) C4 0.032(6) 0.030(6) 0.043(6) -0.004(5) -0.018(6) -0.005(5) C5 0.036(7) 0.050(7) 0.020(5) 0.006(5) -0.006(5) 0.012(5) C6 0.044(7) 0.032(6) 0.044(7) 0.013(6) -0.001(6) 0.000(5) C7 0.027(6) 0.031(6) 0.043(6) -0.010(5) -0.005(5) -0.004(5) C8 0.018(5) 0.040(6) 0.024(5) -0.006(5) -0.003(4) 0.003(5) C9 0.014(5) 0.026(5) 0.047(7) 0.002(5) 0.000(5) -0.009(4) C10 0.031(6) 0.018(5) 0.043(6) 0.000(5) 0.001(5) -0.012(5) C11 0.046(8) 0.030(6) 0.039(6) 0.001(5) 0.013(6) 0.011(6) C12 0.037(7) 0.017(5) 0.058(7) -0.007(5) -0.004(6) -0.001(5) C13 0.031(7) 0.032(6) 0.039(6) 0.002(5) 0.000(5) 0.000(5) C14 0.039(7) 0.027(6) 0.069(8) 0.016(6) -0.006(6) -0.003(5) C15 0.033(7) 0.032(6) 0.070(8) 0.000(6) 0.005(6) 0.002(5) C16 0.055(9) 0.026(6) 0.064(8) -0.010(6) 0.016(7) 0.004(6) C17 0.027(6) 0.026(5) 0.048(7) 0.008(5) 0.002(5) 0.001(5) C18 0.028(6) 0.046(7) 0.033(6) 0.006(5) 0.002(5) 0.003(5) N13 0.047(7) 0.049(6) 0.043(6) 0.003(5) -0.005(5) 0.004(5) C37 0.054(9) 0.061(8) 0.057(8) 0.002(7) 0.006(7) 0.008(7) C38 0.063(10) 0.091(11) 0.056(9) 0.003(8) 0.000(8) 0.014(9) C39 0.054(10) 0.074(10) 0.049(8) -0.001(7) 0.014(7) -0.004(7) C40 0.067(12) 0.097(12) 0.062(9) 0.019(9) -0.004(8) 0.009(9) C41 0.062(10) 0.058(8) 0.048(7) 0.007(7) -0.003(7) 0.021(7) C42 0.085(13) 0.077(10) 0.078(11) 0.003(9) 0.017(9) -0.012(9) C43 0.064(10) 0.072(10) 0.059(9) 0.001(8) -0.012(8) -0.004(8) C44 0.071(12) 0.093(12) 0.060(9) -0.006(9) -0.010(8) -0.018(9) Br1 0.0437(7) 0.0575(8) 0.0356(6) 0.0006(6) -0.0004(6) -0.0032(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 Cl1 C1 1.737(12) . ? Cl2 C11 1.729(11) . ? O1 C2 1.330(13) . ? O1 C17 1.415(12) . ? O2 C12 1.340(13) . ? O2 C13 1.404(12) . ? O3 C10 1.326(12) . ? O3 C8 1.412(11) . ? O4 C3 1.346(12) . ? O4 C4 1.387(12) . ? O5 C15 1.369(14) . ? O5 H5 0.8400 . ? O6 C6 1.358(12) . ? O6 H6 0.8400 . ? N1 C1 1.282(15) . ? N1 C2 1.342(14) . ? N2 C3 1.314(13) . ? N2 C2 1.319(14) . ? N3 C1 1.333(15) . ? N3 C3 1.342(14) . ? N4 C10 1.320(13) . ? N4 C12 1.339(13) . ? N5 C11 1.311(14) . ? N5 C12 1.339(14) . ? N6 C11 1.315(14) . ? N6 C10 1.333(12) . ? C4 C9 1.380(14) . ? C4 C5 1.389(14) . ? C5 C6 1.389(15) . ? C5 H5A 0.9500 . ? C6 C7 1.372(14) . ? C7 C8 1.396(14) . ? C7 H7 0.9500 . ? C8 C9 1.351(13) . ? C9 H9 0.9500 . ? C13 C14 1.369(15) . ? C13 C18 1.373(14) . ? C14 C15 1.389(15) . ? C14 H14 0.9500 . ? C15 C16 1.389(16) . ? C16 C17 1.380(15) . ? C16 H16 0.9500 . ? C17 C18 1.379(14) . ? C18 H18 0.9500 . ? N13 C37 1.484(14) . ? N13 C39 1.487(15) . ? N13 C41 1.492(15) . ? N13 C43 1.508(16) . ? C37 C38 1.503(17) . ? C37 H37B 0.9900 . ? C37 H37A 0.9900 . ? C38 H38A 0.9800 . ? C38 H38B 0.9800 . ? C38 H38C 0.9800 . ? C39 C40 1.546(17) . ? C39 H39A 0.9900 . ? C39 H39B 0.9900 . ? C40 H40C 0.9800 . ? C40 H40B 0.9800 . ? C40 H40A 0.9800 . ? C41 C42 1.513(18) . ? C41 H41A 0.9900 . ? C41 H41B 0.9900 . ? C42 H42B 0.9800 . ? C42 H42A 0.9800 . ? C42 H42C 0.9800 . ? C43 C44 1.519(18) . ? C43 H43B 0.9900 . ? C43 H43A 0.9900 . ? C44 H44C 0.9800 . ? C44 H44A 0.9800 . ? C44 H44B 0.9800 . ? 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 C2 O1 C17 121.0(9) . . ? C12 O2 C13 121.5(9) . . ? C10 O3 C8 121.5(8) . . ? C3 O4 C4 124.6(8) . . ? C15 O5 H5 119.2 . . ? C6 O6 H6 108.4 . . ? C1 N1 C2 112.9(10) . . ? C3 N2 C2 113.2(9) . . ? C1 N3 C3 110.4(10) . . ? C10 N4 C12 112.5(9) . . ? C11 N5 C12 112.6(9) . . ? C11 N6 C10 112.2(9) . . ? N1 C1 N3 129.5(11) . . ? N1 C1 Cl1 118.0(10) . . ? N3 C1 Cl1 112.5(9) . . ? N2 C2 O1 121.6(10) . . ? N2 C2 N1 126.1(11) . . ? O1 C2 N1 112.3(10) . . ? N2 C3 N3 127.8(10) . . ? N2 C3 O4 120.4(9) . . ? N3 C3 O4 111.7(9) . . ? C9 C4 O4 121.9(9) . . ? C9 C4 C5 122.5(9) . . ? O4 C4 C5 114.9(9) . . ? C4 C5 C6 118.8(10) . . ? C4 C5 H5A 120.6 . . ? C6 C5 H5A 120.6 . . ? O6 C6 C7 119.9(10) . . ? O6 C6 C5 120.2(10) . . ? C7 C6 C5 119.9(10) . . ? C6 C7 C8 118.6(9) . . ? C6 C7 H7 120.7 . . ? C8 C7 H7 120.7 . . ? C9 C8 C7 123.6(9) . . ? C9 C8 O3 120.9(9) . . ? C7 C8 O3 114.6(8) . . ? C8 C9 C4 116.6(10) . . ? C8 C9 H9 121.7 . . ? C4 C9 H9 121.7 . . ? N4 C10 O3 119.7(9) . . ? N4 C10 N6 127.7(10) . . ? O3 C10 N6 112.6(9) . . ? N5 C11 N6 128.5(10) . . ? N5 C11 Cl2 115.2(9) . . ? N6 C11 Cl2 116.2(8) . . ? N5 C12 N4 126.5(10) . . ? N5 C12 O2 114.0(10) . . ? N4 C12 O2 119.4(10) . . ? C14 C13 C18 124.2(10) . . ? C14 C13 O2 114.1(10) . . ? C18 C13 O2 121.2(10) . . ? C13 C14 C15 117.9(11) . . ? C13 C14 H14 121.0 . . ? C15 C14 H14 121.0 . . ? O5 C15 C16 118.0(10) . . ? O5 C15 C14 121.3(11) . . ? C16 C15 C14 120.5(11) . . ? C17 C16 C15 118.4(10) . . ? C17 C16 H16 120.8 . . ? C15 C16 H16 120.8 . . ? C18 C17 C16 123.1(10) . . ? C18 C17 O1 120.5(10) . . ? C16 C17 O1 116.0(9) . . ? C13 C18 C17 116.0(10) . . ? C13 C18 H18 122.0 . . ? C17 C18 H18 122.0 . . ? C37 N13 C39 105.0(9) . . ? C37 N13 C41 111.6(10) . . ? C39 N13 C41 112.1(10) . . ? C37 N13 C43 110.3(10) . . ? C39 N13 C43 111.7(10) . . ? C41 N13 C43 106.3(10) . . ? N13 C37 C38 114.4(11) . . ? N13 C37 H37B 108.6 . . ? C38 C37 H37B 108.6 . . ? N13 C37 H37A 108.6 . . ? C38 C37 H37A 108.6 . . ? H37B C37 H37A 107.6 . . ? C37 C38 H38A 109.5 . . ? C37 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C37 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? N13 C39 C40 115.5(12) . . ? N13 C39 H39A 108.4 . . ? C40 C39 H39A 108.4 . . ? N13 C39 H39B 108.4 . . ? C40 C39 H39B 108.4 . . ? H39A C39 H39B 107.5 . . ? C39 C40 H40C 109.5 . . ? C39 C40 H40B 109.5 . . ? H40C C40 H40B 109.5 . . ? C39 C40 H40A 109.5 . . ? H40C C40 H40A 109.5 . . ? H40B C40 H40A 109.5 . . ? N13 C41 C42 116.5(11) . . ? N13 C41 H41A 108.2 . . ? C42 C41 H41A 108.2 . . ? N13 C41 H41B 108.2 . . ? C42 C41 H41B 108.2 . . ? H41A C41 H41B 107.3 . . ? C41 C42 H42B 109.5 . . ? C41 C42 H42A 109.5 . . ? H42B C42 H42A 109.5 . . ? C41 C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? N13 C43 C44 116.0(12) . . ? N13 C43 H43B 108.3 . . ? C44 C43 H43B 108.3 . . ? N13 C43 H43A 108.3 . . ? C44 C43 H43A 108.3 . . ? H43B C43 H43A 107.4 . . ? C43 C44 H44C 109.5 . . ? C43 C44 H44A 109.5 . . ? H44C C44 H44A 109.5 . . ? C43 C44 H44B 109.5 . . ? H44C C44 H44B 109.5 . . ? H44A C44 H44B 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 C2 N1 C1 N3 4(2) . . . . ? C2 N1 C1 Cl1 -176.0(9) . . . . ? C3 N3 C1 N1 -4(2) . . . . ? C3 N3 C1 Cl1 176.6(9) . . . . ? C3 N2 C2 O1 178.0(10) . . . . ? C3 N2 C2 N1 -1.9(17) . . . . ? C17 O1 C2 N2 14.1(16) . . . . ? C17 O1 C2 N1 -166.0(10) . . . . ? C1 N1 C2 N2 -1.3(18) . . . . ? C1 N1 C2 O1 178.8(11) . . . . ? C2 N2 C3 N3 2.6(16) . . . . ? C2 N2 C3 O4 -179.2(10) . . . . ? C1 N3 C3 N2 -0.2(17) . . . . ? C1 N3 C3 O4 -178.4(10) . . . . ? C4 O4 C3 N2 7.4(16) . . . . ? C4 O4 C3 N3 -174.2(10) . . . . ? C3 O4 C4 C9 51.2(15) . . . . ? C3 O4 C4 C5 -138.0(10) . . . . ? C9 C4 C5 C6 -0.2(17) . . . . ? O4 C4 C5 C6 -171.0(10) . . . . ? C4 C5 C6 O6 178.1(10) . . . . ? C4 C5 C6 C7 0.4(17) . . . . ? O6 C6 C7 C8 -178.2(10) . . . . ? C5 C6 C7 C8 -0.5(16) . . . . ? C6 C7 C8 C9 0.4(16) . . . . ? C6 C7 C8 O3 169.8(9) . . . . ? C10 O3 C8 C9 -66.3(13) . . . . ? C10 O3 C8 C7 124.0(10) . . . . ? C7 C8 C9 C4 -0.3(15) . . . . ? O3 C8 C9 C4 -169.1(9) . . . . ? O4 C4 C9 C8 170.3(9) . . . . ? C5 C4 C9 C8 0.2(16) . . . . ? C12 N4 C10 O3 179.1(9) . . . . ? C12 N4 C10 N6 0.0(15) . . . . ? C8 O3 C10 N4 -9.9(14) . . . . ? C8 O3 C10 N6 169.3(8) . . . . ? C11 N6 C10 N4 -1.0(15) . . . . ? C11 N6 C10 O3 179.9(9) . . . . ? C12 N5 C11 N6 0.7(17) . . . . ? C12 N5 C11 Cl2 179.8(8) . . . . ? C10 N6 C11 N5 0.6(17) . . . . ? C10 N6 C11 Cl2 -178.6(7) . . . . ? C11 N5 C12 N4 -1.9(16) . . . . ? C11 N5 C12 O2 -178.2(10) . . . . ? C10 N4 C12 N5 1.6(16) . . . . ? C10 N4 C12 O2 177.7(9) . . . . ? C13 O2 C12 N5 -149.2(9) . . . . ? C13 O2 C12 N4 34.1(15) . . . . ? C12 O2 C13 C14 -147.9(11) . . . . ? C12 O2 C13 C18 40.5(15) . . . . ? C18 C13 C14 C15 1.5(17) . . . . ? O2 C13 C14 C15 -169.9(10) . . . . ? C13 C14 C15 O5 172.1(11) . . . . ? C13 C14 C15 C16 -2.4(18) . . . . ? O5 C15 C16 C17 -172.5(11) . . . . ? C14 C15 C16 C17 2.2(18) . . . . ? C15 C16 C17 C18 -1.0(18) . . . . ? C15 C16 C17 O1 172.2(10) . . . . ? C2 O1 C17 C18 -76.8(14) . . . . ? C2 O1 C17 C16 109.7(12) . . . . ? C14 C13 C18 C17 -0.4(16) . . . . ? O2 C13 C18 C17 170.4(9) . . . . ? C16 C17 C18 C13 0.1(16) . . . . ? O1 C17 C18 C13 -172.8(9) . . . . ? C39 N13 C37 C38 179.9(12) . . . . ? C41 N13 C37 C38 58.3(15) . . . . ? C43 N13 C37 C38 -59.7(15) . . . . ? C37 N13 C39 C40 178.1(12) . . . . ? C41 N13 C39 C40 -60.5(15) . . . . ? C43 N13 C39 C40 58.6(15) . . . . ? C37 N13 C41 C42 53.8(15) . . . . ? C39 N13 C41 C42 -63.7(14) . . . . ? C43 N13 C41 C42 174.0(12) . . . . ? C37 N13 C43 C44 -62.4(15) . . . . ? C39 N13 C43 C44 53.9(15) . . . . ? C41 N13 C43 C44 176.4(11) . . . . ? 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 O5 H5 Br1 0.84 2.33 3.161(9) 170.9 6_556 O6 H6 Br1 0.84 2.72 3.243(8) 122.3 8_566 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.774 _refine_diff_density_min -0.588 _refine_diff_density_rms 0.110 _database_code_depnum_ccdc_archive 'CCDC 968608' data_a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H8 Cl2 N6 O6, C8 H20 N, N O3' _chemical_formula_sum 'C26 H28 Cl2 N8 O9' _chemical_formula_weight 667.46 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 orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 17.539(4) _cell_length_b 17.744(4) _cell_length_c 19.730(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 6140(2) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 20379 _cell_measurement_theta_min 1.5435 _cell_measurement_theta_max 31.1892 _exptl_crystal_description block _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.444 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2768 _exptl_absorpt_coefficient_mu 0.276 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5564 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'CrystalClear (Rigaku Inc., 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Saturn724+ CCD' _diffrn_measurement_method '\w scans at fixed \c = 45\%' _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19758 _diffrn_reflns_av_R_equivalents 0.0682 _diffrn_reflns_av_sigmaI/netI 0.0673 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5389 _reflns_number_gt 4396 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution 'SHELX-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELX-97 (Sheldrick, 2008)' _computing_molecular_graphics ; Mercury: visualization and analysis of crystal structures, C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor, M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006. ; _computing_publication_material 'SHELX-97 (Sheldrick, 2008)' _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^)+(0.1279P)^2^+36.5124P] 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 5389 _refine_ls_number_parameters 420 _refine_ls_number_restraints 20 _refine_ls_R_factor_all 0.2533 _refine_ls_R_factor_gt 0.2288 _refine_ls_wR_factor_ref 0.4713 _refine_ls_wR_factor_gt 0.4569 _refine_ls_goodness_of_fit_ref 1.325 _refine_ls_restrained_S_all 1.324 _refine_ls_shift/su_max 0.058 _refine_ls_shift/su_mean 0.009 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 0.4841(3) 0.0968(2) 0.5027(2) 0.131(2) Uani 1 1 d . . . Cl2 Cl 0.7429(3) 0.5718(3) 0.8620(3) 0.157(2) Uani 1 1 d . . . O1 O 0.5758(5) 0.1260(4) 0.7295(4) 0.073(2) Uani 1 1 d . . . O2 O 0.6625(5) 0.3156(5) 0.8861(5) 0.092(3) Uani 1 1 d . . . O3 O 0.5125(5) 0.4760(4) 0.7608(5) 0.080(2) Uani 1 1 d . . . O4 O 0.3699(5) 0.2654(5) 0.6647(5) 0.086(3) Uani 1 1 d . A . O5 O 0.5596(6) 0.0845(6) 0.9653(5) 0.109(3) Uani 1 1 d . . . H5 H 0.5621 0.1076 1.0024 0.164 Uiso 1 1 d R . . O6 O 0.2518(9) 0.4334(9) 0.8131(14) 0.090(6) Uani 0.64(4) 1 d PDU A 1 H6 H 0.2182 0.4009 0.8052 0.135 Uiso 0.64(4) 1 d PR A 1 O6' O 0.280(2) 0.422(2) 0.8484(16) 0.101(9) Uani 0.36(4) 1 d PDU A 2 H6' H 0.2389 0.3970 0.8474 0.151 Uiso 0.36(4) 1 d PR A 2 O7 O 0.5734(8) 0.2861(7) 0.5921(6) 0.140(5) Uani 1 1 d . . . O8 O 0.6535(9) 0.3212(8) 0.6680(7) 0.151(6) Uani 1 1 d . . . O9 O 0.6218(7) 0.3904(8) 0.5901(6) 0.140(5) Uani 1 1 d . . . N1 N 0.4243(7) 0.1870(6) 0.5927(6) 0.086(3) Uani 1 1 d . . . N2 N 0.5318(7) 0.1150(5) 0.6256(5) 0.074(3) Uani 1 1 d . . . N3 N 0.4719(5) 0.2003(5) 0.7034(4) 0.057(2) Uani 1 1 d . . . N4 N 0.6963(7) 0.4340(8) 0.8685(7) 0.100(4) Uani 1 1 d . . . N5 N 0.5794(6) 0.3909(5) 0.8221(5) 0.066(2) Uani 1 1 d . . . N6 N 0.6184(8) 0.5179(7) 0.8046(7) 0.097(4) Uani 1 1 d . . . N7 N 0.6862(6) 0.6343(7) 0.5686(6) 0.085(3) Uani 1 1 d . . . N8 N 0.6198(7) 0.3253(6) 0.6160(7) 0.084(3) Uani 1 1 d . . . C1 C 0.4819(9) 0.1362(7) 0.5848(7) 0.082(4) Uani 1 1 d . . . C2 C 0.5218(7) 0.1485(6) 0.6859(6) 0.064(3) Uani 1 1 d . . . C3 C 0.4272(6) 0.2148(6) 0.6565(6) 0.064(3) Uani 1 1 d . . . C4 C 0.5800(7) 0.1563(7) 0.7962(6) 0.066(3) Uani 1 1 d . . . C5 C 0.5637(8) 0.1101(7) 0.8492(7) 0.078(4) Uani 1 1 d . . . H5A H 0.5435 0.0612 0.8410 0.093 Uiso 1 1 calc R . . C6 C 0.5759(8) 0.1331(8) 0.9129(7) 0.083(4) Uani 1 1 d . . . C7 C 0.6065(7) 0.2039(8) 0.9260(5) 0.079(4) Uani 1 1 d . . . H7 H 0.6155 0.2204 0.9711 0.094 Uiso 1 1 calc R . . C8 C 0.6228(7) 0.2483(7) 0.8725(5) 0.074(4) Uani 1 1 d . . . C9 C 0.6110(6) 0.2287(6) 0.8054(7) 0.073(3) Uani 1 1 d . . . H9 H 0.6229 0.2613 0.7687 0.087 Uiso 1 1 calc R . . C10 C 0.6440(8) 0.3817(8) 0.8567(7) 0.084(4) Uani 1 1 d . . . C11 C 0.6777(11) 0.4999(9) 0.8428(10) 0.103(5) Uani 1 1 d . . . C12 C 0.5733(8) 0.4591(7) 0.7979(7) 0.077(3) Uani 1 1 d . . . C13 C 0.4480(7) 0.4270(6) 0.7594(6) 0.067(3) Uani 1 1 d . . . C14 C 0.3883(9) 0.4472(7) 0.7943(8) 0.094(5) Uani 1 1 d . A . H14 H 0.3911 0.4907 0.8224 0.113 Uiso 1 1 calc R . . C15 C 0.3212(8) 0.4070(7) 0.7913(8) 0.101(5) Uani 1 1 d D . . C16 C 0.3175(8) 0.3443(7) 0.7491(8) 0.086(4) Uani 1 1 d . A . H16 H 0.2722 0.3150 0.7468 0.103 Uiso 1 1 calc R . . C17 C 0.3786(7) 0.3255(6) 0.7117(7) 0.072(3) Uani 1 1 d . . . C18 C 0.4463(7) 0.3660(7) 0.7168(6) 0.070(3) Uani 1 1 d . A . H18 H 0.4901 0.3518 0.6915 0.084 Uiso 1 1 calc R . . C19 C 0.6285(9) 0.5913(9) 0.5317(8) 0.103(5) Uani 1 1 d . . . H19B H 0.5785 0.6007 0.5534 0.123 Uiso 1 1 calc R . . H19A H 0.6401 0.5370 0.5373 0.123 Uiso 1 1 calc R . . C20 C 0.6204(12) 0.6076(11) 0.4552(10) 0.141(7) Uani 1 1 d . . . H20A H 0.5825 0.5733 0.4356 0.211 Uiso 1 1 calc R . . H20B H 0.6697 0.5999 0.4328 0.211 Uiso 1 1 calc R . . H20C H 0.6038 0.6598 0.4487 0.211 Uiso 1 1 calc R . . C21 C 0.6798(12) 0.7155(8) 0.5602(12) 0.140(7) Uani 1 1 d . . . H21A H 0.6819 0.7284 0.5114 0.168 Uiso 1 1 calc R . . H21B H 0.7229 0.7408 0.5832 0.168 Uiso 1 1 calc R . . C22 C 0.6008(12) 0.7445(10) 0.5918(11) 0.143(7) Uani 1 1 d . . . H22A H 0.5581 0.7240 0.5655 0.214 Uiso 1 1 calc R . . H22C H 0.5991 0.7997 0.5903 0.214 Uiso 1 1 calc R . . H22B H 0.5967 0.7275 0.6390 0.214 Uiso 1 1 calc R . . C23 C 0.6812(12) 0.6049(9) 0.6396(8) 0.116(6) Uani 1 1 d . . . H23B H 0.6295 0.6152 0.6574 0.140 Uiso 1 1 calc R . . H23A H 0.6881 0.5495 0.6386 0.140 Uiso 1 1 calc R . . C24 C 0.7379(14) 0.6376(13) 0.6869(11) 0.165(9) Uani 1 1 d . . . H24A H 0.7889 0.6340 0.6669 0.247 Uiso 1 1 calc R . . H24B H 0.7367 0.6098 0.7298 0.247 Uiso 1 1 calc R . . H24C H 0.7254 0.6906 0.6953 0.247 Uiso 1 1 calc R . . C25 C 0.7625(11) 0.6170(11) 0.5418(11) 0.132(6) Uani 1 1 d . . . H25B H 0.8003 0.6433 0.5705 0.159 Uiso 1 1 calc R . . H25A H 0.7661 0.6390 0.4958 0.159 Uiso 1 1 calc R . . C26 C 0.7858(12) 0.5355(12) 0.5372(10) 0.149(8) Uani 1 1 d . . . H26C H 0.8376 0.5320 0.5189 0.223 Uiso 1 1 calc R . . H26A H 0.7505 0.5085 0.5073 0.223 Uiso 1 1 calc R . . H26B H 0.7844 0.5128 0.5825 0.223 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 0.222(5) 0.086(3) 0.085(3) -0.039(2) -0.038(3) 0.043(3) Cl2 0.129(4) 0.121(4) 0.221(6) 0.013(4) -0.030(4) -0.059(3) O1 0.092(6) 0.046(4) 0.080(6) -0.005(4) 0.013(5) 0.011(4) O2 0.107(7) 0.061(5) 0.109(7) -0.022(5) -0.041(6) -0.004(5) O3 0.088(6) 0.050(4) 0.103(7) 0.007(4) 0.007(5) -0.008(5) O4 0.087(6) 0.065(5) 0.108(7) -0.018(5) -0.045(5) 0.019(5) O5 0.134(9) 0.126(8) 0.068(6) 0.004(6) 0.003(6) -0.026(7) O6 0.093(10) 0.064(8) 0.114(13) -0.015(8) 0.010(9) -0.008(7) O6' 0.107(14) 0.077(12) 0.117(15) -0.013(13) -0.003(13) -0.004(12) O7 0.171(11) 0.129(9) 0.119(9) 0.004(7) 0.018(8) -0.097(9) O8 0.186(13) 0.169(12) 0.098(8) 0.060(8) -0.049(9) -0.054(10) O9 0.150(11) 0.143(11) 0.128(9) 0.013(8) -0.046(8) -0.054(9) N1 0.098(8) 0.063(6) 0.097(8) -0.013(6) -0.039(7) -0.004(6) N2 0.121(9) 0.049(5) 0.052(6) -0.001(4) -0.016(6) 0.015(6) N3 0.046(5) 0.057(5) 0.067(5) -0.019(4) -0.025(4) 0.005(4) N4 0.090(8) 0.078(8) 0.132(11) -0.021(8) -0.002(7) -0.019(7) N5 0.068(6) 0.069(6) 0.060(6) -0.013(5) 0.002(5) -0.012(5) N6 0.088(8) 0.078(8) 0.126(11) -0.006(7) -0.011(8) -0.012(7) N7 0.068(7) 0.099(9) 0.089(8) 0.003(7) -0.005(6) -0.017(6) N8 0.090(8) 0.063(7) 0.098(9) 0.032(6) 0.023(7) -0.038(6) C1 0.131(12) 0.046(7) 0.069(8) -0.018(6) 0.001(8) 0.010(8) C2 0.075(7) 0.053(6) 0.064(7) 0.025(6) -0.006(6) 0.007(6) C3 0.053(6) 0.045(6) 0.095(8) -0.011(6) -0.052(6) -0.004(5) C4 0.068(7) 0.071(8) 0.059(7) -0.006(6) 0.007(6) 0.021(6) C5 0.090(9) 0.062(7) 0.081(9) -0.006(7) 0.018(7) 0.013(7) C6 0.089(9) 0.096(10) 0.064(8) -0.031(8) 0.004(7) -0.017(8) C7 0.088(8) 0.119(11) 0.029(5) -0.012(6) -0.031(5) 0.020(8) C8 0.094(9) 0.091(9) 0.036(6) -0.023(6) -0.040(6) 0.031(7) C9 0.069(7) 0.052(7) 0.097(9) 0.027(6) 0.011(7) 0.014(6) C10 0.081(9) 0.074(9) 0.096(10) -0.035(8) 0.014(8) -0.014(8) C11 0.104(12) 0.074(10) 0.131(14) -0.023(10) 0.035(11) -0.046(10) C12 0.079(9) 0.054(8) 0.099(10) -0.013(7) 0.001(8) -0.006(7) C13 0.071(7) 0.062(7) 0.068(7) 0.009(6) 0.021(6) 0.026(6) C14 0.113(11) 0.042(6) 0.128(12) -0.001(7) 0.049(10) -0.025(7) C15 0.123(12) 0.054(8) 0.127(12) -0.027(8) 0.075(10) 0.015(8) C16 0.074(8) 0.059(7) 0.125(11) 0.007(8) 0.013(8) 0.034(7) C17 0.069(8) 0.053(7) 0.094(9) 0.005(6) -0.042(7) 0.027(6) C18 0.057(7) 0.075(8) 0.078(8) -0.014(6) 0.002(6) 0.041(6) C19 0.113(12) 0.105(11) 0.089(10) 0.026(9) 0.019(9) -0.019(10) C20 0.142(16) 0.123(15) 0.157(18) 0.011(13) -0.040(14) 0.006(12) C21 0.157(18) 0.057(9) 0.21(2) 0.028(11) -0.032(16) 0.000(11) C22 0.160(17) 0.087(11) 0.181(19) 0.022(12) -0.052(15) 0.017(13) C23 0.153(16) 0.097(12) 0.098(12) 0.015(9) -0.033(11) -0.013(11) C24 0.19(2) 0.142(18) 0.166(19) 0.023(15) -0.054(18) 0.001(17) C25 0.117(15) 0.113(15) 0.166(18) 0.014(13) -0.012(13) -0.003(12) C26 0.159(18) 0.161(19) 0.127(15) 0.018(14) 0.003(13) 0.058(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 C1 1.764(12) . ? Cl2 C11 1.755(15) . ? O1 C2 1.340(13) . ? O1 C4 1.423(13) . ? O2 C10 1.349(17) . ? O2 C8 1.407(15) . ? O3 C12 1.329(15) . ? O3 C13 1.426(14) . ? O4 C3 1.358(13) . ? O4 C17 1.421(14) . ? O5 C6 1.376(16) . ? O5 H5 0.8400 . ? O6 C15 1.374(9) . ? O6 H6 0.8397 . ? O6 H6' 0.9623 . ? O6' C15 1.366(10) . ? O6' H6' 0.8401 . ? O7 N8 1.171(14) . ? O8 N8 1.186(15) . ? O9 N8 1.264(15) . ? N1 C3 1.355(15) . ? N1 C1 1.361(17) . ? N2 C1 1.248(16) . ? N2 C2 1.343(14) . ? N3 C3 1.240(12) . ? N3 C2 1.315(14) . ? N4 C11 1.32(2) . ? N4 C10 1.325(17) . ? N5 C12 1.305(15) . ? N5 C10 1.333(17) . ? N6 C12 1.315(16) . ? N6 C11 1.32(2) . ? N7 C21 1.455(18) . ? N7 C19 1.461(18) . ? N7 C25 1.47(2) . ? N7 C23 1.499(18) . ? C4 C5 1.360(16) . ? C4 C9 1.407(16) . ? C5 C6 1.338(17) . ? C5 H5A 0.9500 . ? C6 C7 1.390(18) . ? C7 C8 1.349(17) . ? C7 H7 0.9500 . ? C8 C9 1.385(16) . ? C9 H9 0.9500 . ? C13 C14 1.305(16) . ? C13 C18 1.371(16) . ? C14 C15 1.376(18) . ? C14 H14 0.9500 . ? C15 C16 1.393(18) . ? C16 C17 1.343(17) . ? C16 H16 0.9500 . ? C17 C18 1.392(16) . ? C18 H18 0.9500 . ? C19 C20 1.54(2) . ? C19 H19B 0.9900 . ? C19 H19A 0.9900 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 C22 1.61(3) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 H22A 0.9800 . ? C22 H22C 0.9800 . ? C22 H22B 0.9800 . ? C23 C24 1.48(2) . ? C23 H23B 0.9900 . ? C23 H23A 0.9900 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 C26 1.51(2) . ? C25 H25B 0.9900 . ? C25 H25A 0.9900 . ? C26 H26C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? 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 C2 O1 C4 121.2(9) . . ? C10 O2 C8 122.5(10) . . ? C12 O3 C13 120.6(9) . . ? C3 O4 C17 119.6(8) . . ? C6 O5 H5 109.8 . . ? C15 O6 H6 109.3 . . ? C15 O6 H6' 101.4 . . ? H6 O6 H6' 60.3 . . ? C15 O6' H6 82.0 . . ? C15 O6' H6' 109.5 . . ? H6 O6' H6' 37.3 . . ? C3 N1 C1 108.7(10) . . ? C1 N2 C2 110.3(11) . . ? C3 N3 C2 111.7(10) . . ? C11 N4 C10 112.6(14) . . ? C12 N5 C10 111.7(12) . . ? C12 N6 C11 109.8(13) . . ? C21 N7 C19 114.0(13) . . ? C21 N7 C25 103.7(14) . . ? C19 N7 C25 110.0(13) . . ? C21 N7 C23 116.5(14) . . ? C19 N7 C23 104.1(11) . . ? C25 N7 C23 108.5(14) . . ? O7 N8 O8 131.3(12) . . ? O7 N8 O9 113.5(14) . . ? O8 N8 O9 113.1(13) . . ? N2 C1 N1 130.3(11) . . ? N2 C1 Cl1 117.2(10) . . ? N1 C1 Cl1 112.6(11) . . ? N3 C2 O1 120.6(10) . . ? N3 C2 N2 129.0(10) . . ? O1 C2 N2 110.2(10) . . ? N3 C3 N1 130.0(11) . . ? N3 C3 O4 121.1(11) . . ? N1 C3 O4 108.9(9) . . ? C5 C4 C9 122.2(11) . . ? C5 C4 O1 118.2(11) . . ? C9 C4 O1 118.9(11) . . ? C6 C5 C4 120.3(13) . . ? C6 C5 H5A 119.9 . . ? C4 C5 H5A 119.9 . . ? C5 C6 O5 118.7(12) . . ? C5 C6 C7 120.9(13) . . ? O5 C6 C7 120.4(11) . . ? C8 C7 C6 117.7(10) . . ? C8 C7 H7 121.2 . . ? C6 C7 H7 121.2 . . ? C7 C8 C9 124.7(12) . . ? C7 C8 O2 116.9(9) . . ? C9 C8 O2 118.0(12) . . ? C8 C9 C4 114.3(11) . . ? C8 C9 H9 122.8 . . ? C4 C9 H9 122.8 . . ? N4 C10 N5 126.4(15) . . ? N4 C10 O2 111.6(14) . . ? N5 C10 O2 122.0(12) . . ? N4 C11 N6 128.9(13) . . ? N4 C11 Cl2 113.8(16) . . ? N6 C11 Cl2 117.3(14) . . ? N5 C12 N6 130.5(14) . . ? N5 C12 O3 118.4(11) . . ? N6 C12 O3 111.0(13) . . ? C14 C13 C18 121.6(13) . . ? C14 C13 O3 117.3(11) . . ? C18 C13 O3 120.7(10) . . ? C13 C14 C15 121.4(13) . . ? C13 C14 H14 119.3 . . ? C15 C14 H14 119.3 . . ? O6' C15 O6 37.3(15) . . ? O6' C15 C14 109(2) . . ? O6 C15 C14 124.5(13) . . ? O6' C15 C16 128.4(19) . . ? O6 C15 C16 114.7(15) . . ? C14 C15 C16 118.7(11) . . ? C17 C16 C15 119.3(13) . . ? C17 C16 H16 120.4 . . ? C15 C16 H16 120.4 . . ? C16 C17 C18 120.9(12) . . ? C16 C17 O4 117.3(12) . . ? C18 C17 O4 121.7(12) . . ? C13 C18 C17 118.1(11) . . ? C13 C18 H18 121.0 . . ? C17 C18 H18 121.0 . . ? N7 C19 C20 116.9(13) . . ? N7 C19 H19B 108.1 . . ? C20 C19 H19B 108.1 . . ? N7 C19 H19A 108.1 . . ? C20 C19 H19A 108.1 . . ? H19B C19 H19A 107.3 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? N7 C21 C22 109.9(15) . . ? N7 C21 H21A 109.7 . . ? C22 C21 H21A 109.7 . . ? N7 C21 H21B 109.7 . . ? C22 C21 H21B 109.7 . . ? H21A C21 H21B 108.2 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? H22C C22 H22B 109.5 . . ? C24 C23 N7 114.4(15) . . ? C24 C23 H23B 108.7 . . ? N7 C23 H23B 108.6 . . ? C24 C23 H23A 108.7 . . ? N7 C23 H23A 108.7 . . ? H23B C23 H23A 107.6 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? N7 C25 C26 118.0(16) . . ? N7 C25 H25B 107.8 . . ? C26 C25 H25B 107.8 . . ? N7 C25 H25A 107.8 . . ? C26 C25 H25A 107.8 . . ? H25B C25 H25A 107.2 . . ? C25 C26 H26C 109.5 . . ? C25 C26 H26A 109.5 . . ? H26C C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26C C26 H26B 109.5 . . ? H26A C26 H26B 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 C2 N2 C1 N1 2(2) . . . . ? C2 N2 C1 Cl1 -178.7(9) . . . . ? C3 N1 C1 N2 0(2) . . . . ? C3 N1 C1 Cl1 -179.5(9) . . . . ? C3 N3 C2 O1 179.0(10) . . . . ? C3 N3 C2 N2 4.1(17) . . . . ? C4 O1 C2 N3 1.2(15) . . . . ? C4 O1 C2 N2 176.9(10) . . . . ? C1 N2 C2 N3 -4.3(18) . . . . ? C1 N2 C2 O1 -179.6(10) . . . . ? C2 N3 C3 N1 -1.7(18) . . . . ? C2 N3 C3 O4 178.3(10) . . . . ? C1 N1 C3 N3 0.0(18) . . . . ? C1 N1 C3 O4 180.0(10) . . . . ? C17 O4 C3 N3 28.3(17) . . . . ? C17 O4 C3 N1 -151.7(11) . . . . ? C2 O1 C4 C5 111.8(12) . . . . ? C2 O1 C4 C9 -77.2(13) . . . . ? C9 C4 C5 C6 0.9(19) . . . . ? O1 C4 C5 C6 171.7(11) . . . . ? C4 C5 C6 O5 -179.2(12) . . . . ? C4 C5 C6 C7 -1(2) . . . . ? C5 C6 C7 C8 0(2) . . . . ? O5 C6 C7 C8 178.6(12) . . . . ? C6 C7 C8 C9 0(2) . . . . ? C6 C7 C8 O2 -172.1(11) . . . . ? C10 O2 C8 C7 -137.1(12) . . . . ? C10 O2 C8 C9 49.9(17) . . . . ? C7 C8 C9 C4 -0.3(18) . . . . ? O2 C8 C9 C4 172.1(10) . . . . ? C5 C4 C9 C8 -0.3(17) . . . . ? O1 C4 C9 C8 -171.0(10) . . . . ? C11 N4 C10 N5 1(2) . . . . ? C11 N4 C10 O2 -177.1(12) . . . . ? C12 N5 C10 N4 2.0(18) . . . . ? C12 N5 C10 O2 -179.8(12) . . . . ? C8 O2 C10 N4 -169.8(12) . . . . ? C8 O2 C10 N5 11.8(19) . . . . ? C10 N4 C11 N6 -5(2) . . . . ? C10 N4 C11 Cl2 176.3(10) . . . . ? C12 N6 C11 N4 5(2) . . . . ? C12 N6 C11 Cl2 -176.8(10) . . . . ? C10 N5 C12 N6 -3(2) . . . . ? C10 N5 C12 O3 178.5(11) . . . . ? C11 N6 C12 N5 0(2) . . . . ? C11 N6 C12 O3 178.7(12) . . . . ? C13 O3 C12 N5 13.2(17) . . . . ? C13 O3 C12 N6 -165.9(11) . . . . ? C12 O3 C13 C14 103.9(14) . . . . ? C12 O3 C13 C18 -83.5(15) . . . . ? C18 C13 C14 C15 2(2) . . . . ? O3 C13 C14 C15 174.3(13) . . . . ? C13 C14 C15 O6' 158(2) . . . . ? C13 C14 C15 O6 -164.0(19) . . . . ? C13 C14 C15 C16 -1(2) . . . . ? O6' C15 C16 C17 -155(3) . . . . ? O6 C15 C16 C17 163.4(16) . . . . ? C14 C15 C16 C17 -1(2) . . . . ? C15 C16 C17 C18 2.8(19) . . . . ? C15 C16 C17 O4 -174.3(12) . . . . ? C3 O4 C17 C16 -140.1(12) . . . . ? C3 O4 C17 C18 42.9(16) . . . . ? C14 C13 C18 C17 -0.2(18) . . . . ? O3 C13 C18 C17 -172.4(10) . . . . ? C16 C17 C18 C13 -2.1(17) . . . . ? O4 C17 C18 C13 174.7(10) . . . . ? C21 N7 C19 C20 53(2) . . . . ? C25 N7 C19 C20 -62.8(19) . . . . ? C23 N7 C19 C20 -178.8(15) . . . . ? C19 N7 C21 C22 64.1(19) . . . . ? C25 N7 C21 C22 -176.3(15) . . . . ? C23 N7 C21 C22 -57(2) . . . . ? C21 N7 C23 C24 -57(2) . . . . ? C19 N7 C23 C24 177.0(16) . . . . ? C25 N7 C23 C24 60(2) . . . . ? C21 N7 C25 C26 -174.9(17) . . . . ? C19 N7 C25 C26 -53(2) . . . . ? C23 N7 C25 C26 61(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 O5 H5 O9 0.84 2.02 2.729(16) 141.3 7_566 O5 H5 O7 0.84 2.59 3.404(16) 162.3 7_566 O6 H6 O8 0.84 1.89 2.66(2) 152.1 6_557 O6 H6 N8 0.84 2.68 3.32(2) 133.4 6_557 O6' H6' O8 0.84 2.04 2.86(4) 167.5 6_557 O6' H6' O9 0.84 2.40 3.07(3) 137.9 6_557 O6' H6' N8 0.84 2.55 3.36(4) 162.1 6_557 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.869 _refine_diff_density_min -0.382 _refine_diff_density_rms 0.090 _database_code_depnum_ccdc_archive 'CCDC 968609' data_a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H34 Cl4 N12 O17' _chemical_formula_weight 1144.63 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 13.470(3) _cell_length_b 12.046(2) _cell_length_c 30.738(6) _cell_angle_alpha 90.00 _cell_angle_beta 92.59(3) _cell_angle_gamma 90.00 _cell_volume 4982.6(17) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 17512 _cell_measurement_theta_min 1.5133 _cell_measurement_theta_max 31.2237 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.526 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2344 _exptl_absorpt_coefficient_mu 0.323 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5952 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'CrystalClear (Rigaku Inc., 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Saturn724+ CCD' _diffrn_measurement_method '\w scans at fixed \c = 45\%' _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28962 _diffrn_reflns_av_R_equivalents 0.0662 _diffrn_reflns_av_sigmaI/netI 0.0706 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 25.00 _reflns_number_total 8753 _reflns_number_gt 7716 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution 'SHELX-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELX-97 (Sheldrick, 2008)' _computing_molecular_graphics ; Mercury: visualization and analysis of crystal structures, C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor, M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006. ; _computing_publication_material 'SHELX-97 (Sheldrick, 2008)' _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^)+(0.0619P)^2^+15.5004P] 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 8753 _refine_ls_number_parameters 741 _refine_ls_number_restraints 436 _refine_ls_R_factor_all 0.1316 _refine_ls_R_factor_gt 0.1180 _refine_ls_wR_factor_ref 0.2509 _refine_ls_wR_factor_gt 0.2428 _refine_ls_goodness_of_fit_ref 1.279 _refine_ls_restrained_S_all 1.251 _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 0.51861(11) 0.68582(14) 0.16057(6) 0.0499(4) Uani 1 1 d . . . Cl2 Cl 1.25881(12) 0.60271(15) 0.40352(5) 0.0503(4) Uani 1 1 d . . . Cl3 Cl 0.36655(12) 0.55493(15) 0.24191(6) 0.0520(4) Uani 1 1 d . . . Cl4 Cl 1.04522(17) 0.2406(2) 0.50961(8) 0.0827(7) Uani 1 1 d . . . O1 O 1.1393(3) 0.7764(5) 0.10727(14) 0.0613(14) Uani 1 1 d . . . H1 H 1.2005 0.7894 0.1070 0.074 Uiso 1 1 d R . . O2 O 1.1002(3) 0.3002(4) 0.13870(15) 0.0544(12) Uani 1 1 d . . . H2 H 1.1526 0.2690 0.1482 0.065 Uiso 1 1 d R . . O3 O 0.8535(3) 0.8148(3) 0.18937(15) 0.0464(11) Uani 1 1 d . . . O4 O 0.7973(3) 0.4382(3) 0.18753(15) 0.0460(11) Uani 1 1 d . . . O5 O 1.0821(3) 0.4094(3) 0.28775(14) 0.0423(10) Uani 1 1 d . . . O6 O 1.1727(3) 0.7712(3) 0.26370(13) 0.0401(10) Uani 1 1 d . . . O7 O 0.9556(3) 0.8590(4) 0.34208(17) 0.0576(13) Uani 1 1 d . . . H7 H 0.9188 0.9099 0.3319 0.069 Uiso 1 1 d R . . O9 O 0.4924(3) 0.5506(4) 0.39135(14) 0.0492(11) Uani 1 1 d . A . O10 O 0.7145(3) 0.5998(4) 0.28371(14) 0.0447(10) Uani 1 1 d . . . O11 O 0.9742(3) 0.4837(4) 0.38773(15) 0.0484(11) Uani 1 1 d . . . O13 O 1.1658(3) 0.3004(4) 0.38874(15) 0.0496(11) Uani 1 1 d . . . H13B H 1.1756 0.3656 0.3803 0.060 Uiso 1 1 d R . . H13A H 1.1249 0.3082 0.4084 0.060 Uiso 1 1 d R . . O14 O 0.7176(5) 0.9122(6) 0.5475(2) 0.094(2) Uani 1 1 d . . . O15 O 0.7254(6) 0.9970(6) 0.6125(2) 0.110(2) Uani 1 1 d . . . N1 N 0.6699(3) 0.5550(4) 0.17591(16) 0.0371(11) Uani 1 1 d . . . N2 N 0.6979(4) 0.7504(4) 0.17894(17) 0.0425(12) Uani 1 1 d . . . N3 N 0.8340(3) 0.6247(4) 0.18899(16) 0.0366(11) Uani 1 1 d . . . N4 N 1.1678(3) 0.5022(4) 0.33957(15) 0.0360(11) Uani 1 1 d . . . N5 N 1.1207(3) 0.5913(4) 0.27244(15) 0.0335(11) Uani 1 1 d . . . N6 N 1.2149(3) 0.6900(4) 0.32770(15) 0.0365(11) Uani 1 1 d . . . N7 N 0.4376(4) 0.5537(4) 0.32184(18) 0.0446(13) Uani 1 1 d . . . N8 N 0.5530(4) 0.5771(4) 0.26578(17) 0.0445(13) Uani 1 1 d . . . N9 N 0.6100(4) 0.5809(4) 0.34076(16) 0.0388(12) Uani 1 1 d . . . N10 N 0.8929(5) 0.3723(6) 0.5027(2) 0.072(2) Uani 1 1 d . A . N11 N 0.8610(4) 0.4905(5) 0.44103(17) 0.0468(13) Uani 1 1 d . A . N12 N 1.0024(4) 0.3707(5) 0.44443(19) 0.0519(14) Uani 1 1 d . . . C1 C 0.6420(4) 0.6618(5) 0.1736(2) 0.0387(14) Uani 1 1 d . . . C2 C 0.7675(4) 0.5448(5) 0.18464(19) 0.0358(13) Uani 1 1 d . . . C3 C 0.7943(4) 0.7245(5) 0.18561(19) 0.0356(13) Uani 1 1 d . . . C4 C 0.9574(4) 0.7954(5) 0.1885(2) 0.0374(14) Uani 1 1 d . . . C5 C 0.9987(4) 0.7896(5) 0.1489(2) 0.0451(16) Uani 1 1 d . . . H5 H 0.9579 0.7921 0.1228 0.054 Uiso 1 1 calc R . . C6 C 1.1014(5) 0.7801(5) 0.1471(2) 0.0428(15) Uani 1 1 d . . . C7 C 1.1593(4) 0.7697(5) 0.1858(2) 0.0421(15) Uani 1 1 d . . . H7A H 1.2292 0.7596 0.1852 0.051 Uiso 1 1 calc R . . C8 C 1.1128(4) 0.7746(5) 0.22437(19) 0.0387(14) Uani 1 1 d . . . C9 C 1.0120(4) 0.7891(5) 0.2272(2) 0.0371(13) Uani 1 1 d . . . H9 H 0.9819 0.7945 0.2545 0.045 Uiso 1 1 calc R . . C10 C 1.1680(4) 0.6794(5) 0.28831(19) 0.0341(13) Uani 1 1 d . . . C11 C 1.2097(4) 0.5972(5) 0.35078(19) 0.0369(14) Uani 1 1 d . . . C12 C 1.1247(4) 0.5062(5) 0.29960(19) 0.0341(13) Uani 1 1 d . . . C13 C 1.0379(5) 0.4008(5) 0.2449(2) 0.0388(14) Uani 1 1 d . . . C14 C 1.0943(4) 0.3590(5) 0.2134(2) 0.0379(14) Uani 1 1 d . . . H14 H 1.1623 0.3411 0.2193 0.045 Uiso 1 1 calc R . . C15 C 1.0498(4) 0.3428(5) 0.1721(2) 0.0411(14) Uani 1 1 d . . . C16 C 0.9508(4) 0.3708(5) 0.1632(2) 0.0435(15) Uani 1 1 d . . . H16 H 0.9202 0.3603 0.1351 0.052 Uiso 1 1 calc R . . C17 C 0.8985(4) 0.4143(5) 0.1966(2) 0.0387(14) Uani 1 1 d . . . C18 C 0.9387(4) 0.4294(5) 0.2382(2) 0.0396(14) Uani 1 1 d . . . H18 H 0.9005 0.4577 0.2610 0.048 Uiso 1 1 calc R . . C19 C 0.4628(4) 0.5616(5) 0.2807(2) 0.0408(14) Uani 1 1 d . . . C20 C 0.5160(4) 0.5626(5) 0.3502(2) 0.0415(15) Uani 1 1 d . . . C21 C 0.6222(4) 0.5858(5) 0.2987(2) 0.0374(14) Uani 1 1 d . . . C22 C 0.7948(4) 0.6231(5) 0.3144(2) 0.0397(14) Uani 1 1 d . . . C23 C 0.8311(4) 0.7298(5) 0.3136(2) 0.0408(14) Uani 1 1 d . . . H23 H 0.8009 0.7843 0.2950 0.049 Uiso 1 1 calc R . . C24 C 0.9135(4) 0.7554(5) 0.3407(2) 0.0412(15) Uani 1 1 d . . . C25 C 0.9587(4) 0.6729(5) 0.3665(2) 0.0424(15) Uani 1 1 d . . . H25 H 1.0153 0.6894 0.3849 0.051 Uiso 1 1 calc R . . C26 C 0.9203(5) 0.5683(5) 0.3648(2) 0.0429(15) Uani 1 1 d . . . C27 C 0.8374(4) 0.5383(5) 0.3391(2) 0.0421(15) Uani 1 1 d . . . H27 H 0.8117 0.4649 0.3385 0.051 Uiso 1 1 calc R . . C28 C 0.9429(5) 0.4484(5) 0.4259(2) 0.0467(16) Uani 1 1 d . . . C29 C 0.9721(5) 0.3391(6) 0.4822(3) 0.0579(19) Uani 1 1 d . . . C30 C 0.8399(5) 0.4486(7) 0.4789(2) 0.060(2) Uani 1 1 d D . . O8 O 0.5991(5) 0.8436(5) 0.4824(2) 0.0699(17) Uani 0.792(5) 1 d PDU A 1 H8 H 0.6329 0.8582 0.5054 0.084 Uiso 0.792(5) 1 d PR A 1 O12 O 0.7609(5) 0.4891(6) 0.4991(2) 0.0542(15) Uani 0.792(5) 1 d PDU A 1 C31 C 0.6924(6) 0.5584(7) 0.4764(3) 0.0479(15) Uani 0.792(5) 1 d PDU A 1 C32 C 0.6838(6) 0.6667(6) 0.4910(3) 0.0508(16) Uani 0.792(5) 1 d PDU A 1 H32 H 0.7258 0.6937 0.5143 0.061 Uiso 0.792(5) 1 calc PR A 1 C33 C 0.6125(6) 0.7347(6) 0.4708(3) 0.0540(16) Uani 0.792(5) 1 d PDU A 1 C34 C 0.5500(6) 0.6956(6) 0.4372(3) 0.0485(16) Uani 0.792(5) 1 d PDU A 1 H34 H 0.5017 0.7423 0.4230 0.058 Uiso 0.792(5) 1 calc PR A 1 C36 C 0.6359(6) 0.5175(7) 0.4413(3) 0.0465(18) Uani 0.792(5) 1 d PDU A 1 H36 H 0.6482 0.4466 0.4291 0.056 Uiso 0.792(5) 1 calc PR A 1 O8A O 0.5496(18) 0.7509(19) 0.5247(8) 0.0699(17) Uani 0.208(5) 1 d PDU A 2 H8A H 0.5765 0.7431 0.5497 0.084 Uiso 0.208(5) 1 d PR A 2 O12A O 0.7478(14) 0.436(2) 0.4956(9) 0.0542(15) Uani 0.208(5) 1 d PDU A 2 C31A C 0.679(2) 0.512(2) 0.4799(9) 0.0479(15) Uani 0.208(5) 1 d PDU A 2 C32A C 0.656(2) 0.596(2) 0.5088(9) 0.0508(16) Uani 0.208(5) 1 d PDU A 2 H32A H 0.6932 0.6045 0.5356 0.061 Uiso 0.208(5) 1 calc PR A 2 C33A C 0.578(2) 0.667(2) 0.4979(8) 0.0540(16) Uani 0.208(5) 1 d PDU A 2 C34A C 0.528(2) 0.655(3) 0.4576(7) 0.0485(16) Uani 0.208(5) 1 d PDU A 2 H34A H 0.4692 0.6964 0.4519 0.058 Uiso 0.208(5) 1 calc PR A 2 C36A C 0.614(3) 0.498(2) 0.4438(12) 0.0465(18) Uani 0.208(5) 1 d PDU A 2 H36A H 0.6062 0.4261 0.4316 0.056 Uiso 0.208(5) 1 calc PR A 2 C35 C 0.5609(4) 0.5855(5) 0.4249(2) 0.0478(14) Uani 1 1 d DU . . C37 C 0.5614(7) 0.9629(10) 0.5797(4) 0.107(4) Uani 1 1 d . . . H37B H 0.5399 1.0347 0.5676 0.161 Uiso 1 1 calc R . . H37C H 0.5418 0.9573 0.6100 0.161 Uiso 1 1 calc R . . H37A H 0.5302 0.9029 0.5625 0.161 Uiso 1 1 calc R . . C38 C 0.6740(8) 0.9534(8) 0.5783(3) 0.084(3) Uani 1 1 d . . . C39 C 0.8336(7) 1.0009(10) 0.6099(4) 0.106(4) Uani 1 1 d . . . H39B H 0.8644 1.0133 0.6394 0.127 Uiso 1 1 calc R . . H39A H 0.8578 0.9289 0.5991 0.127 Uiso 1 1 calc R . . C40 C 0.8631(10) 1.0897(10) 0.5809(4) 0.123(4) Uani 1 1 d . . . H40A H 0.8337 1.0766 0.5516 0.185 Uiso 1 1 calc R . . H40B H 0.9357 1.0910 0.5798 0.185 Uiso 1 1 calc R . . H40C H 0.8398 1.1611 0.5919 0.185 Uiso 1 1 calc R . . O16 O 0.7124(16) 0.2187(14) 0.4217(5) 0.121(3) Uani 0.632(12) 1 d PDU B 1 O17 O 0.7694(12) 0.1082(13) 0.4732(5) 0.122(2) Uani 0.632(12) 1 d PDU B 1 C41 C 0.6337(18) 0.234(2) 0.4905(6) 0.117(3) Uani 0.632(12) 1 d PDU B 1 H41C H 0.6661 0.2936 0.5076 0.175 Uiso 0.632(12) 1 calc PR B 1 H41B H 0.6130 0.1750 0.5100 0.175 Uiso 0.632(12) 1 calc PR B 1 H41A H 0.5752 0.2640 0.4743 0.175 Uiso 0.632(12) 1 calc PR B 1 C42 C 0.706(2) 0.188(2) 0.4588(7) 0.118(2) Uani 0.632(12) 1 d PDU B 1 C43 C 0.8333(16) 0.0667(15) 0.4405(7) 0.128(3) Uani 0.632(12) 1 d PDU B 1 H43B H 0.9035 0.0668 0.4516 0.153 Uiso 0.632(12) 1 calc PR B 1 H43A H 0.8275 0.1131 0.4139 0.153 Uiso 0.632(12) 1 calc PR B 1 C44 C 0.7977(17) -0.0530(15) 0.4307(7) 0.129(3) Uani 0.632(12) 1 d PDU B 1 H44B H 0.8403 -0.0868 0.4093 0.193 Uiso 0.632(12) 1 calc PR B 1 H44A H 0.7289 -0.0512 0.4188 0.193 Uiso 0.632(12) 1 calc PR B 1 H44C H 0.8012 -0.0967 0.4576 0.193 Uiso 0.632(12) 1 calc PR B 1 O16A O 0.706(3) 0.257(2) 0.4305(9) 0.121(3) Uani 0.368(12) 1 d PDU B 2 O17A O 0.715(2) 0.084(2) 0.4652(8) 0.122(2) Uani 0.368(12) 1 d PDU B 2 C41A C 0.654(3) 0.217(4) 0.5040(10) 0.117(3) Uani 0.368(12) 1 d PDU B 2 H41F H 0.7084 0.2141 0.5264 0.175 Uiso 0.368(12) 1 calc PR B 2 H41D H 0.6043 0.1608 0.5104 0.175 Uiso 0.368(12) 1 calc PR B 2 H41E H 0.6239 0.2905 0.5037 0.175 Uiso 0.368(12) 1 calc PR B 2 C42A C 0.695(5) 0.193(2) 0.4599(13) 0.118(2) Uani 0.368(12) 1 d PDU B 2 C43A C 0.755(2) 0.031(4) 0.4281(9) 0.128(3) Uani 0.368(12) 1 d PDU B 2 H43C H 0.7534 0.0805 0.4024 0.153 Uiso 0.368(12) 1 calc PR B 2 H43D H 0.7202 -0.0391 0.4206 0.153 Uiso 0.368(12) 1 calc PR B 2 C44A C 0.863(2) 0.010(4) 0.4458(12) 0.129(3) Uani 0.368(12) 1 d PDU B 2 H44D H 0.8900 -0.0547 0.4311 0.193 Uiso 0.368(12) 1 calc PR B 2 H44F H 0.8627 -0.0042 0.4772 0.193 Uiso 0.368(12) 1 calc PR B 2 H44E H 0.9037 0.0753 0.4404 0.193 Uiso 0.368(12) 1 calc PR B 2 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 0.0268(7) 0.0479(9) 0.0739(11) 0.0026(8) -0.0075(7) 0.0037(7) Cl2 0.0480(9) 0.0650(11) 0.0372(8) 0.0082(8) -0.0045(7) -0.0082(8) Cl3 0.0430(9) 0.0575(10) 0.0546(10) -0.0027(8) -0.0079(7) 0.0013(8) Cl4 0.0758(14) 0.0955(17) 0.0774(14) 0.0349(13) 0.0098(11) 0.0283(13) O1 0.049(3) 0.095(4) 0.040(3) 0.002(3) -0.001(2) -0.020(3) O2 0.046(3) 0.057(3) 0.060(3) -0.008(2) -0.003(2) 0.018(2) O3 0.031(2) 0.031(2) 0.077(3) 0.006(2) -0.007(2) -0.0013(18) O4 0.028(2) 0.028(2) 0.081(3) -0.010(2) -0.007(2) 0.0033(17) O5 0.044(2) 0.032(2) 0.051(3) 0.0087(19) -0.008(2) -0.0029(19) O6 0.037(2) 0.038(2) 0.045(2) 0.0076(19) -0.0050(18) -0.0098(19) O7 0.042(3) 0.036(2) 0.094(4) 0.002(2) -0.012(2) -0.001(2) O9 0.040(2) 0.063(3) 0.044(3) -0.002(2) 0.002(2) -0.002(2) O10 0.037(2) 0.045(2) 0.052(3) -0.006(2) 0.0025(19) -0.006(2) O11 0.044(3) 0.048(3) 0.055(3) 0.010(2) 0.011(2) 0.010(2) O13 0.043(2) 0.044(3) 0.063(3) 0.014(2) 0.010(2) -0.001(2) O14 0.107(5) 0.092(5) 0.083(4) -0.023(4) 0.008(4) -0.007(4) O15 0.113(6) 0.109(6) 0.106(6) -0.031(5) -0.019(4) 0.020(5) N1 0.024(2) 0.035(3) 0.052(3) -0.003(2) -0.004(2) -0.001(2) N2 0.032(3) 0.038(3) 0.057(3) 0.005(2) -0.005(2) 0.002(2) N3 0.027(2) 0.030(3) 0.052(3) 0.003(2) -0.002(2) 0.003(2) N4 0.028(3) 0.040(3) 0.039(3) 0.008(2) 0.000(2) -0.004(2) N5 0.029(2) 0.032(3) 0.039(3) 0.004(2) 0.000(2) -0.002(2) N6 0.032(3) 0.043(3) 0.034(3) 0.006(2) 0.001(2) -0.004(2) N7 0.041(3) 0.041(3) 0.051(3) -0.001(3) -0.001(2) 0.003(2) N8 0.039(3) 0.041(3) 0.054(3) -0.004(3) 0.001(2) 0.001(2) N9 0.037(3) 0.036(3) 0.043(3) -0.004(2) 0.001(2) 0.000(2) N10 0.057(4) 0.103(6) 0.055(4) 0.021(4) 0.007(3) 0.020(4) N11 0.043(3) 0.059(3) 0.039(3) -0.001(3) 0.005(2) 0.010(3) N12 0.047(3) 0.051(3) 0.058(4) 0.008(3) 0.009(3) 0.006(3) C1 0.030(3) 0.038(3) 0.048(4) 0.000(3) -0.007(3) 0.002(3) C2 0.031(3) 0.030(3) 0.047(3) -0.005(3) -0.001(3) 0.000(3) C3 0.030(3) 0.031(3) 0.046(3) 0.003(3) -0.003(3) 0.000(3) C4 0.027(3) 0.030(3) 0.055(4) 0.009(3) -0.005(3) -0.006(2) C5 0.036(3) 0.050(4) 0.047(4) 0.010(3) -0.016(3) -0.011(3) C6 0.038(3) 0.046(4) 0.044(4) 0.002(3) -0.007(3) -0.011(3) C7 0.030(3) 0.044(4) 0.051(4) 0.007(3) -0.004(3) -0.005(3) C8 0.039(3) 0.036(3) 0.040(3) 0.003(3) -0.010(3) -0.008(3) C9 0.027(3) 0.034(3) 0.050(4) 0.004(3) 0.000(3) -0.008(2) C10 0.025(3) 0.038(3) 0.039(3) 0.006(3) 0.002(2) -0.001(3) C11 0.024(3) 0.043(3) 0.044(3) 0.002(3) 0.003(2) 0.000(3) C12 0.026(3) 0.036(3) 0.041(3) 0.003(3) 0.000(2) 0.000(2) C13 0.044(3) 0.026(3) 0.046(4) 0.005(3) -0.009(3) -0.005(3) C14 0.028(3) 0.032(3) 0.053(4) -0.002(3) -0.004(3) 0.004(3) C15 0.038(3) 0.032(3) 0.052(4) -0.006(3) 0.000(3) 0.007(3) C16 0.040(3) 0.038(3) 0.051(4) -0.007(3) -0.004(3) 0.002(3) C17 0.028(3) 0.026(3) 0.061(4) 0.005(3) -0.003(3) 0.002(2) C18 0.037(3) 0.029(3) 0.053(4) -0.003(3) 0.006(3) -0.006(3) C19 0.036(3) 0.033(3) 0.053(4) -0.005(3) -0.003(3) 0.005(3) C20 0.038(3) 0.037(3) 0.050(4) -0.007(3) 0.000(3) 0.005(3) C21 0.030(3) 0.030(3) 0.052(4) -0.007(3) 0.002(3) 0.000(2) C22 0.031(3) 0.041(3) 0.047(4) -0.004(3) 0.004(3) 0.000(3) C23 0.037(3) 0.032(3) 0.054(4) -0.003(3) 0.004(3) -0.001(3) C24 0.030(3) 0.031(3) 0.063(4) 0.000(3) 0.008(3) 0.000(3) C25 0.028(3) 0.038(3) 0.062(4) 0.001(3) 0.004(3) -0.001(3) C26 0.042(4) 0.040(3) 0.047(4) 0.004(3) 0.011(3) 0.005(3) C27 0.040(3) 0.039(3) 0.049(4) -0.008(3) 0.005(3) -0.006(3) C28 0.038(3) 0.044(4) 0.058(4) -0.001(3) -0.003(3) 0.004(3) C29 0.049(4) 0.060(5) 0.065(5) 0.012(4) -0.001(4) 0.009(4) C30 0.037(4) 0.089(6) 0.054(4) -0.006(4) 0.001(3) 0.017(4) O8 0.071(4) 0.069(4) 0.069(4) -0.025(3) -0.012(3) 0.003(3) O12 0.051(3) 0.065(4) 0.047(3) 0.003(3) 0.006(2) 0.016(3) C31 0.041(3) 0.060(3) 0.043(3) -0.002(3) 0.008(2) 0.007(3) C32 0.044(3) 0.064(3) 0.044(3) -0.008(3) 0.002(3) 0.005(3) C33 0.049(3) 0.060(3) 0.053(3) -0.013(3) 0.002(3) 0.003(3) C34 0.040(3) 0.059(4) 0.047(3) -0.008(3) 0.002(3) 0.004(3) C36 0.038(4) 0.058(3) 0.044(3) -0.007(3) 0.009(3) 0.001(3) O8A 0.071(4) 0.069(4) 0.069(4) -0.025(3) -0.012(3) 0.003(3) O12A 0.051(3) 0.065(4) 0.047(3) 0.003(3) 0.006(2) 0.016(3) C31A 0.041(3) 0.060(3) 0.043(3) -0.002(3) 0.008(2) 0.007(3) C32A 0.044(3) 0.064(3) 0.044(3) -0.008(3) 0.002(3) 0.005(3) C33A 0.049(3) 0.060(3) 0.053(3) -0.013(3) 0.002(3) 0.003(3) C34A 0.040(3) 0.059(4) 0.047(3) -0.008(3) 0.002(3) 0.004(3) C36A 0.038(4) 0.058(3) 0.044(3) -0.007(3) 0.009(3) 0.001(3) C35 0.040(3) 0.060(3) 0.044(3) -0.008(3) 0.005(3) 0.007(3) C37 0.088(7) 0.105(8) 0.129(10) -0.023(7) 0.010(7) 0.004(6) C38 0.099(7) 0.081(6) 0.071(6) -0.026(5) -0.017(5) 0.020(6) C39 0.064(6) 0.104(8) 0.145(10) -0.001(8) -0.035(6) 0.006(6) C40 0.138(11) 0.092(8) 0.138(11) 0.026(8) -0.015(8) -0.015(8) O16 0.143(5) 0.132(5) 0.087(5) 0.014(4) 0.016(4) 0.013(5) O17 0.145(5) 0.125(4) 0.099(4) 0.000(4) 0.017(4) 0.022(4) C41 0.138(5) 0.125(5) 0.089(5) 0.011(5) 0.021(5) 0.013(5) C42 0.141(4) 0.126(4) 0.088(4) 0.011(4) 0.017(4) 0.015(4) C43 0.153(5) 0.128(5) 0.104(5) -0.006(5) 0.015(5) 0.022(5) C44 0.154(6) 0.127(6) 0.106(5) -0.006(5) 0.011(5) 0.024(6) O16A 0.143(5) 0.132(5) 0.087(5) 0.014(4) 0.016(4) 0.013(5) O17A 0.145(5) 0.125(4) 0.099(4) 0.000(4) 0.017(4) 0.022(4) C41A 0.138(5) 0.125(5) 0.089(5) 0.011(5) 0.021(5) 0.013(5) C42A 0.141(4) 0.126(4) 0.088(4) 0.011(4) 0.017(4) 0.015(4) C43A 0.153(5) 0.128(5) 0.104(5) -0.006(5) 0.015(5) 0.022(5) C44A 0.154(6) 0.127(6) 0.106(5) -0.006(5) 0.011(5) 0.024(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 Cl1 C1 1.716(6) . ? Cl2 C11 1.724(6) . ? Cl3 C19 1.723(6) . ? Cl4 C29 1.736(7) . ? O1 C6 1.348(8) . ? O1 H1 0.8400 . ? O2 C15 1.356(7) . ? O2 H2 0.8398 . ? O3 C3 1.350(7) . ? O3 C4 1.421(7) . ? O4 C2 1.347(7) . ? O4 C17 1.410(7) . ? O5 C12 1.343(7) . ? O5 C13 1.424(7) . ? O6 C10 1.343(7) . ? O6 C8 1.423(7) . ? O7 C24 1.371(7) . ? O7 H7 0.8400 . ? O9 C20 1.327(7) . ? O9 C35 1.416(7) . ? O10 C21 1.355(7) . ? O10 C22 1.432(7) . ? O11 C28 1.334(8) . ? O11 C26 1.420(7) . ? O13 H13B 0.8399 . ? O13 H13A 0.8399 . ? O14 C38 1.239(10) . ? O15 C38 1.339(10) . ? O15 C39 1.464(11) . ? N1 C2 1.336(7) . ? N1 C1 1.342(7) . ? N2 C1 1.313(8) . ? N2 C3 1.342(7) . ? N3 C2 1.317(7) . ? N3 C3 1.318(7) . ? N4 C11 1.315(7) . ? N4 C12 1.335(7) . ? N5 C10 1.321(7) . ? N5 C12 1.321(7) . ? N6 C11 1.328(7) . ? N6 C10 1.346(7) . ? N7 C19 1.328(8) . ? N7 C20 1.343(8) . ? N8 C19 1.331(8) . ? N8 C21 1.347(8) . ? N9 C21 1.313(8) . ? N9 C20 1.330(8) . ? N10 C29 1.326(9) . ? N10 C30 1.356(9) . ? N11 C30 1.312(9) . ? N11 C28 1.318(8) . ? N12 C29 1.304(9) . ? N12 C28 1.343(8) . ? C4 C5 1.363(9) . ? C4 C9 1.374(8) . ? C5 C6 1.392(8) . ? C5 H5 0.9500 . ? C6 C7 1.398(8) . ? C7 C8 1.368(9) . ? C7 H7A 0.9500 . ? C8 C9 1.376(8) . ? C9 H9 0.9500 . ? C13 C14 1.356(8) . ? C13 C18 1.386(8) . ? C14 C15 1.393(8) . ? C14 H14 0.9500 . ? C15 C16 1.392(8) . ? C16 C17 1.374(9) . ? C16 H16 0.9500 . ? C17 C18 1.377(9) . ? C18 H18 0.9500 . ? C22 C23 1.375(8) . ? C22 C27 1.382(9) . ? C23 C24 1.393(8) . ? C23 H23 0.9500 . ? C24 C25 1.394(9) . ? C25 C26 1.363(8) . ? C25 H25 0.9500 . ? C26 C27 1.386(9) . ? C27 H27 0.9500 . ? C30 O12 1.348(8) . ? C30 O12A 1.372(17) . ? O8 C33 1.374(7) . ? O8 H8 0.8400 . ? O12 C31 1.407(9) . ? C31 C36 1.383(8) . ? C31 C32 1.385(8) . ? C32 C33 1.388(8) . ? C32 H32 0.9500 . ? C33 C34 1.385(8) . ? C34 C35 1.388(7) . ? C34 H34 0.9500 . ? C36 C35 1.379(7) . ? C36 H36 0.9500 . ? O8A C33A 1.367(10) . ? O8A H8A 0.8398 . ? O12A C31A 1.374(18) . ? C31A C36A 1.388(10) . ? C31A C32A 1.391(10) . ? C32A C33A 1.387(10) . ? C32A H32A 0.9500 . ? C33A C34A 1.388(10) . ? C34A C35 1.393(10) . ? C34A H34A 0.9500 . ? C36A C35 1.387(10) . ? C36A H36A 0.9500 . ? C37 C38 1.523(13) . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? C37 H37A 0.9800 . ? C39 C40 1.459(14) . ? C39 H39B 0.9900 . ? C39 H39A 0.9900 . ? C40 H40A 0.9800 . ? C40 H40B 0.9800 . ? C40 H40C 0.9800 . ? O16 C42 1.207(9) . ? O17 C42 1.347(10) . ? O17 C43 1.441(9) . ? C41 C42 1.513(9) . ? C41 H41C 0.9800 . ? C41 H41B 0.9800 . ? C41 H41A 0.9800 . ? C43 C44 1.546(10) . ? C43 H43B 0.9900 . ? C43 H43A 0.9900 . ? C44 H44B 0.9800 . ? C44 H44A 0.9800 . ? C44 H44C 0.9800 . ? O16A C42A 1.206(10) . ? O17A C42A 1.346(10) . ? O17A C43A 1.436(10) . ? C41A C42A 1.513(10) . ? C41A H41F 0.9800 . ? C41A H41D 0.9800 . ? C41A H41E 0.9800 . ? C43A C44A 1.546(10) . ? C43A H43C 0.9900 . ? C43A H43D 0.9900 . ? C44A H44D 0.9800 . ? C44A H44F 0.9800 . ? C44A H44E 0.9800 . ? 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 H1 114.6 . . ? C15 O2 H2 110.4 . . ? C3 O3 C4 116.4(4) . . ? C2 O4 C17 119.4(4) . . ? C12 O5 C13 118.0(4) . . ? C10 O6 C8 117.6(4) . . ? C24 O7 H7 114.6 . . ? C20 O9 C35 119.1(5) . . ? C21 O10 C22 118.6(5) . . ? C28 O11 C26 119.3(5) . . ? H13B O13 H13A 103.6 . . ? C38 O15 C39 116.9(9) . . ? C2 N1 C1 111.7(5) . . ? C1 N2 C3 112.1(5) . . ? C2 N3 C3 112.8(5) . . ? C11 N4 C12 111.9(5) . . ? C10 N5 C12 112.6(5) . . ? C11 N6 C10 111.5(5) . . ? C19 N7 C20 112.6(5) . . ? C19 N8 C21 111.3(5) . . ? C21 N9 C20 112.6(5) . . ? C29 N10 C30 111.3(6) . . ? C30 N11 C28 112.6(6) . . ? C29 N12 C28 112.1(6) . . ? N2 C1 N1 128.0(5) . . ? N2 C1 Cl1 115.9(4) . . ? N1 C1 Cl1 116.1(4) . . ? N3 C2 N1 127.7(5) . . ? N3 C2 O4 119.4(5) . . ? N1 C2 O4 112.8(5) . . ? N3 C3 N2 127.6(5) . . ? N3 C3 O3 119.5(5) . . ? N2 C3 O3 112.9(5) . . ? C5 C4 C9 123.2(5) . . ? C5 C4 O3 117.9(5) . . ? C9 C4 O3 118.8(6) . . ? C4 C5 C6 119.1(6) . . ? C4 C5 H5 120.5 . . ? C6 C5 H5 120.5 . . ? O1 C6 C5 117.2(5) . . ? O1 C6 C7 123.3(6) . . ? C5 C6 C7 119.4(6) . . ? C8 C7 C6 118.3(6) . . ? C8 C7 H7A 120.8 . . ? C6 C7 H7A 120.8 . . ? C7 C8 C9 123.5(6) . . ? C7 C8 O6 118.1(5) . . ? C9 C8 O6 118.2(5) . . ? C4 C9 C8 116.3(6) . . ? C4 C9 H9 121.9 . . ? C8 C9 H9 121.9 . . ? N5 C10 O6 119.2(5) . . ? N5 C10 N6 127.4(5) . . ? O6 C10 N6 113.4(5) . . ? N4 C11 N6 128.7(6) . . ? N4 C11 Cl2 114.9(4) . . ? N6 C11 Cl2 116.3(5) . . ? N5 C12 N4 127.8(5) . . ? N5 C12 O5 119.8(5) . . ? N4 C12 O5 112.4(5) . . ? C14 C13 C18 123.5(6) . . ? C14 C13 O5 117.6(5) . . ? C18 C13 O5 118.7(6) . . ? C13 C14 C15 118.2(5) . . ? C13 C14 H14 120.9 . . ? C15 C14 H14 120.9 . . ? O2 C15 C16 116.9(6) . . ? O2 C15 C14 122.2(5) . . ? C16 C15 C14 120.9(6) . . ? C17 C16 C15 117.7(6) . . ? C17 C16 H16 121.1 . . ? C15 C16 H16 121.1 . . ? C16 C17 C18 123.4(6) . . ? C16 C17 O4 116.9(6) . . ? C18 C17 O4 119.5(6) . . ? C17 C18 C13 116.2(6) . . ? C17 C18 H18 121.9 . . ? C13 C18 H18 121.9 . . ? N7 C19 N8 128.0(6) . . ? N7 C19 Cl3 116.0(5) . . ? N8 C19 Cl3 116.0(5) . . ? O9 C20 N9 119.8(5) . . ? O9 C20 N7 113.2(5) . . ? N9 C20 N7 126.9(6) . . ? N9 C21 N8 128.5(5) . . ? N9 C21 O10 119.8(5) . . ? N8 C21 O10 111.7(5) . . ? C23 C22 C27 124.2(6) . . ? C23 C22 O10 115.4(5) . . ? C27 C22 O10 120.0(5) . . ? C22 C23 C24 118.0(6) . . ? C22 C23 H23 121.0 . . ? C24 C23 H23 121.0 . . ? O7 C24 C23 122.5(6) . . ? O7 C24 C25 117.5(5) . . ? C23 C24 C25 119.9(6) . . ? C26 C25 C24 118.8(6) . . ? C26 C25 H25 120.6 . . ? C24 C25 H25 120.6 . . ? C25 C26 C27 123.9(6) . . ? C25 C26 O11 117.4(6) . . ? C27 C26 O11 118.5(6) . . ? C22 C27 C26 115.1(6) . . ? C22 C27 H27 122.5 . . ? C26 C27 H27 122.5 . . ? N11 C28 O11 119.4(6) . . ? N11 C28 N12 127.7(6) . . ? O11 C28 N12 112.9(6) . . ? N12 C29 N10 128.8(7) . . ? N12 C29 Cl4 116.0(5) . . ? N10 C29 Cl4 115.2(6) . . ? N11 C30 O12 118.5(7) . . ? N11 C30 N10 127.5(6) . . ? O12 C30 N10 113.9(7) . . ? N11 C30 O12A 127.5(13) . . ? O12 C30 O12A 28.4(11) . . ? N10 C30 O12A 100.8(12) . . ? C33 O8 H8 110.2 . . ? C30 O12 C31 120.0(7) . . ? C36 C31 C32 122.5(8) . . ? C36 C31 O12 120.1(7) . . ? C32 C31 O12 117.4(7) . . ? C31 C32 C33 118.5(7) . . ? C31 C32 H32 120.8 . . ? C33 C32 H32 120.8 . . ? O8 C33 C34 115.9(6) . . ? O8 C33 C32 122.9(7) . . ? C34 C33 C32 121.2(7) . . ? C33 C34 C35 117.4(7) . . ? C33 C34 H34 121.3 . . ? C35 C34 H34 121.3 . . ? C35 C36 C31 116.2(8) . . ? C35 C36 H36 121.9 . . ? C31 C36 H36 121.9 . . ? C33A O8A H8A 110.4 . . ? C30 O12A C31A 114(2) . . ? O12A C31A C36A 126(2) . . ? O12A C31A C32A 115(2) . . ? C36A C31A C32A 117(3) . . ? C33A C32A C31A 119(2) . . ? C33A C32A H32A 120.5 . . ? C31A C32A H32A 120.5 . . ? O8A C33A C32A 123(2) . . ? O8A C33A C34A 118.8(18) . . ? C32A C33A C34A 118(2) . . ? C33A C34A C35 123.7(19) . . ? C33A C34A H34A 118.1 . . ? C35 C34A H34A 118.1 . . ? C35 C36A C31A 123(2) . . ? C35 C36A H36A 118.7 . . ? C31A C36A H36A 118.7 . . ? C36 C35 C36A 16.0(18) . . ? C36 C35 C34 123.5(7) . . ? C36A C35 C34 132.0(15) . . ? C36 C35 C34A 110.0(13) . . ? C36A C35 C34A 109(2) . . ? C34 C35 C34A 35.9(14) . . ? C36 C35 O9 122.2(6) . . ? C36A C35 O9 112.9(14) . . ? C34 C35 O9 114.1(5) . . ? C34A C35 O9 119.2(12) . . ? C38 C37 H37B 109.5 . . ? C38 C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C38 C37 H37A 109.5 . . ? H37B C37 H37A 109.5 . . ? H37C C37 H37A 109.5 . . ? O14 C38 O15 120.6(10) . . ? O14 C38 C37 123.9(9) . . ? O15 C38 C37 115.4(9) . . ? C40 C39 O15 110.8(9) . . ? C40 C39 H39B 109.5 . . ? O15 C39 H39B 109.5 . . ? C40 C39 H39A 109.5 . . ? O15 C39 H39A 109.5 . . ? H39B C39 H39A 108.1 . . ? C39 C40 H40A 109.5 . . ? C39 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? C39 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? C42 O17 C43 114.2(17) . . ? O16 C42 O17 117.1(18) . . ? O16 C42 C41 124.9(16) . . ? O17 C42 C41 118.0(16) . . ? O17 C43 C44 105.6(16) . . ? O17 C43 H43B 110.6 . . ? C44 C43 H43B 110.6 . . ? O17 C43 H43A 110.6 . . ? C44 C43 H43A 110.6 . . ? H43B C43 H43A 108.7 . . ? C42A O17A C43A 115(3) . . ? C42A C41A H41F 109.5 . . ? C42A C41A H41D 109.5 . . ? H41F C41A H41D 109.5 . . ? C42A C41A H41E 109.5 . . ? H41F C41A H41E 109.5 . . ? H41D C41A H41E 109.5 . . ? O16A C42A O17A 133(3) . . ? O16A C42A C41A 128(3) . . ? O17A C42A C41A 99(3) . . ? O17A C43A C44A 100(3) . . ? O17A C43A H43C 111.7 . . ? C44A C43A H43C 111.7 . . ? O17A C43A H43D 111.7 . . ? C44A C43A H43D 111.7 . . ? H43C C43A H43D 109.5 . . ? C43A C44A H44D 109.5 . . ? C43A C44A H44F 109.5 . . ? H44D C44A H44F 109.5 . . ? C43A C44A H44E 109.5 . . ? H44D C44A H44E 109.5 . . ? H44F C44A H44E 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 C3 N2 C1 N1 2.9(9) . . . . ? C3 N2 C1 Cl1 -175.0(4) . . . . ? C2 N1 C1 N2 -0.2(9) . . . . ? C2 N1 C1 Cl1 177.7(4) . . . . ? C3 N3 C2 N1 2.7(9) . . . . ? C3 N3 C2 O4 -179.7(5) . . . . ? C1 N1 C2 N3 -2.9(9) . . . . ? C1 N1 C2 O4 179.4(5) . . . . ? C17 O4 C2 N3 2.1(9) . . . . ? C17 O4 C2 N1 180.0(5) . . . . ? C2 N3 C3 N2 0.6(9) . . . . ? C2 N3 C3 O3 -180.0(5) . . . . ? C1 N2 C3 N3 -3.1(9) . . . . ? C1 N2 C3 O3 177.4(5) . . . . ? C4 O3 C3 N3 11.7(8) . . . . ? C4 O3 C3 N2 -168.8(5) . . . . ? C3 O3 C4 C5 85.5(7) . . . . ? C3 O3 C4 C9 -97.8(7) . . . . ? C9 C4 C5 C6 -1.9(10) . . . . ? O3 C4 C5 C6 174.6(5) . . . . ? C4 C5 C6 O1 -179.0(6) . . . . ? C4 C5 C6 C7 4.0(9) . . . . ? O1 C6 C7 C8 -179.9(6) . . . . ? C5 C6 C7 C8 -3.0(9) . . . . ? C6 C7 C8 C9 0.1(9) . . . . ? C6 C7 C8 O6 -176.0(5) . . . . ? C10 O6 C8 C7 -110.2(6) . . . . ? C10 O6 C8 C9 73.5(7) . . . . ? C5 C4 C9 C8 -1.0(9) . . . . ? O3 C4 C9 C8 -177.5(5) . . . . ? C7 C8 C9 C4 1.9(9) . . . . ? O6 C8 C9 C4 178.0(5) . . . . ? C12 N5 C10 O6 178.0(5) . . . . ? C12 N5 C10 N6 -1.7(8) . . . . ? C8 O6 C10 N5 9.8(8) . . . . ? C8 O6 C10 N6 -170.5(5) . . . . ? C11 N6 C10 N5 0.5(8) . . . . ? C11 N6 C10 O6 -179.2(5) . . . . ? C12 N4 C11 N6 -1.3(8) . . . . ? C12 N4 C11 Cl2 175.3(4) . . . . ? C10 N6 C11 N4 1.2(8) . . . . ? C10 N6 C11 Cl2 -175.3(4) . . . . ? C10 N5 C12 N4 1.6(8) . . . . ? C10 N5 C12 O5 -178.4(5) . . . . ? C11 N4 C12 N5 -0.2(8) . . . . ? C11 N4 C12 O5 179.7(5) . . . . ? C13 O5 C12 N5 3.1(8) . . . . ? C13 O5 C12 N4 -176.9(5) . . . . ? C12 O5 C13 C14 93.9(6) . . . . ? C12 O5 C13 C18 -89.8(6) . . . . ? C18 C13 C14 C15 -0.6(9) . . . . ? O5 C13 C14 C15 175.6(5) . . . . ? C13 C14 C15 O2 -179.2(5) . . . . ? C13 C14 C15 C16 1.2(9) . . . . ? O2 C15 C16 C17 -179.9(5) . . . . ? C14 C15 C16 C17 -0.3(9) . . . . ? C15 C16 C17 C18 -1.2(9) . . . . ? C15 C16 C17 O4 -177.7(5) . . . . ? C2 O4 C17 C16 -108.9(6) . . . . ? C2 O4 C17 C18 74.5(7) . . . . ? C16 C17 C18 C13 1.7(9) . . . . ? O4 C17 C18 C13 178.1(5) . . . . ? C14 C13 C18 C17 -0.8(9) . . . . ? O5 C13 C18 C17 -176.9(5) . . . . ? C20 N7 C19 N8 -0.3(9) . . . . ? C20 N7 C19 Cl3 -178.3(4) . . . . ? C21 N8 C19 N7 -0.6(9) . . . . ? C21 N8 C19 Cl3 177.4(4) . . . . ? C35 O9 C20 N9 16.3(8) . . . . ? C35 O9 C20 N7 -164.0(5) . . . . ? C21 N9 C20 O9 177.0(5) . . . . ? C21 N9 C20 N7 -2.6(9) . . . . ? C19 N7 C20 O9 -177.6(5) . . . . ? C19 N7 C20 N9 2.1(9) . . . . ? C20 N9 C21 N8 1.5(9) . . . . ? C20 N9 C21 O10 -177.5(5) . . . . ? C19 N8 C21 N9 -0.1(9) . . . . ? C19 N8 C21 O10 179.0(5) . . . . ? C22 O10 C21 N9 -7.9(8) . . . . ? C22 O10 C21 N8 173.0(5) . . . . ? C21 O10 C22 C23 -108.4(6) . . . . ? C21 O10 C22 C27 78.3(7) . . . . ? C27 C22 C23 C24 -2.9(9) . . . . ? O10 C22 C23 C24 -175.9(5) . . . . ? C22 C23 C24 O7 179.7(6) . . . . ? C22 C23 C24 C25 2.2(9) . . . . ? O7 C24 C25 C26 -178.1(6) . . . . ? C23 C24 C25 C26 -0.5(9) . . . . ? C24 C25 C26 C27 -0.8(10) . . . . ? C24 C25 C26 O11 173.3(5) . . . . ? C28 O11 C26 C25 102.7(7) . . . . ? C28 O11 C26 C27 -82.9(7) . . . . ? C23 C22 C27 C26 1.7(9) . . . . ? O10 C22 C27 C26 174.3(5) . . . . ? C25 C26 C27 C22 0.2(9) . . . . ? O11 C26 C27 C22 -173.7(5) . . . . ? C30 N11 C28 O11 -179.5(6) . . . . ? C30 N11 C28 N12 0.6(10) . . . . ? C26 O11 C28 N11 1.9(9) . . . . ? C26 O11 C28 N12 -178.2(5) . . . . ? C29 N12 C28 N11 -1.6(10) . . . . ? C29 N12 C28 O11 178.4(6) . . . . ? C28 N12 C29 N10 0.9(12) . . . . ? C28 N12 C29 Cl4 -178.7(5) . . . . ? C30 N10 C29 N12 0.6(13) . . . . ? C30 N10 C29 Cl4 -179.7(6) . . . . ? C28 N11 C30 O12 176.4(7) . . . . ? C28 N11 C30 N10 1.3(12) . . . . ? C28 N11 C30 O12A -151.2(17) . . . . ? C29 N10 C30 N11 -1.9(12) . . . . ? C29 N10 C30 O12 -177.2(7) . . . . ? C29 N10 C30 O12A 156.2(14) . . . . ? N11 C30 O12 C31 12.0(11) . . . . ? N10 C30 O12 C31 -172.2(7) . . . . ? O12A C30 O12 C31 -105(3) . . . . ? C30 O12 C31 C36 64.7(11) . . . . ? C30 O12 C31 C32 -116.1(9) . . . . ? C36 C31 C32 C33 3.1(13) . . . . ? O12 C31 C32 C33 -176.1(8) . . . . ? C31 C32 C33 O8 -179.0(8) . . . . ? C31 C32 C33 C34 0.9(14) . . . . ? O8 C33 C34 C35 -179.3(8) . . . . ? C32 C33 C34 C35 0.8(13) . . . . ? C32 C31 C36 C35 -8.4(13) . . . . ? O12 C31 C36 C35 170.8(7) . . . . ? N11 C30 O12A C31A -27(3) . . . . ? O12 C30 O12A C31A 54(2) . . . . ? N10 C30 O12A C31A 174(2) . . . . ? C30 O12A C31A C36A 91(4) . . . . ? C30 O12A C31A C32A -105(3) . . . . ? O12A C31A C32A C33A -172(3) . . . . ? C36A C31A C32A C33A -6(5) . . . . ? C31A C32A C33A O8A 179(3) . . . . ? C31A C32A C33A C34A -3(5) . . . . ? O8A C33A C34A C35 169(3) . . . . ? C32A C33A C34A C35 -9(5) . . . . ? O12A C31A C36A C35 -167(3) . . . . ? C32A C31A C36A C35 30(5) . . . . ? C31 C36 C35 C36A -117(7) . . . . ? C31 C36 C35 C34 10.3(12) . . . . ? C31 C36 C35 C34A -27.3(19) . . . . ? C31 C36 C35 O9 -174.8(7) . . . . ? C31A C36A C35 C36 57(5) . . . . ? C31A C36A C35 C34 -6(5) . . . . ? C31A C36A C35 C34A -39(4) . . . . ? C31A C36A C35 O9 -174(3) . . . . ? C33 C34 C35 C36 -6.7(13) . . . . ? C33 C34 C35 C36A 11(3) . . . . ? C33 C34 C35 C34A 71(2) . . . . ? C33 C34 C35 O9 178.0(7) . . . . ? C33A C34A C35 C36 11(4) . . . . ? C33A C34A C35 C36A 28(4) . . . . ? C33A C34A C35 C34 -109(4) . . . . ? C33A C34A C35 O9 160(3) . . . . ? C20 O9 C35 C36 -86.2(8) . . . . ? C20 O9 C35 C36A -101(2) . . . . ? C20 O9 C35 C34 89.2(7) . . . . ? C20 O9 C35 C34A 129.1(18) . . . . ? C39 O15 C38 O14 4.5(14) . . . . ? C39 O15 C38 C37 -173.2(9) . . . . ? C38 O15 C39 C40 75.6(12) . . . . ? C43 O17 C42 O16 -4(4) . . . . ? C43 O17 C42 C41 178(2) . . . . ? C42 O17 C43 C44 -110(3) . . . . ? C43A O17A C42A O16A -1(10) . . . . ? C43A O17A C42A C41A 179(4) . . . . ? C42A O17A C43A C44A 110(4) . . . . ? 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 O1 H1 O13 0.84 1.80 2.639(6) 171.9 2_755 O2 H2 N6 0.84 2.13 2.966(6) 179.9 2_745 O2 H2 Cl2 0.84 2.85 3.343(5) 119.2 2_745 O7 H7 N1 0.84 2.13 2.942(6) 164.0 2_655 O13 H13B N4 0.84 2.07 2.864(6) 158.0 . O13 H13A N12 0.84 2.16 2.971(7) 161.1 . O8 H8 O14 0.84 1.81 2.636(9) 167.6 . O8A H8A O1 0.84 1.94 2.78(3) 179.4 4_576 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.472 _refine_diff_density_min -0.472 _refine_diff_density_rms 0.082 _database_code_depnum_ccdc_archive 'CCDC 968610'