# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_a417 _database_code_depnum_ccdc_archive 'CCDC 838392' #TrackingRef 'web_deposit_cif_file_1_OngWeiQiang_1312792022.A417.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H32 Cl2 N10 O8' _chemical_formula_weight 851.66 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 P2(1)2(1)2(1) 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' _cell_length_a 10.5103(13) _cell_length_b 13.6620(16) _cell_length_c 25.537(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3666.9(8) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 731 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 19.99 _exptl_crystal_description Rod _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.543 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1760 _exptl_absorpt_coefficient_mu 0.250 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9066 _exptl_absorpt_correction_T_max 0.9611 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26068 _diffrn_reflns_av_R_equivalents 0.0848 _diffrn_reflns_av_sigmaI/netI 0.0941 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 27.49 _reflns_number_total 8409 _reflns_number_gt 6316 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0797P)^2^+3.0167P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.0(2) _refine_ls_number_reflns 8409 _refine_ls_number_parameters 572 _refine_ls_number_restraints 35 _refine_ls_R_factor_all 0.1167 _refine_ls_R_factor_gt 0.0866 _refine_ls_wR_factor_ref 0.2012 _refine_ls_wR_factor_gt 0.1850 _refine_ls_goodness_of_fit_ref 1.101 _refine_ls_restrained_S_all 1.129 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1S C 0.1643(11) 0.287(2) 0.9511(8) 0.100 Uiso 0.50 1 d PD A 1 H1S1 H 0.1700 0.2565 0.9159 0.120 Uiso 0.50 1 calc PR A 1 H1S2 H 0.1565 0.3587 0.9469 0.120 Uiso 0.50 1 calc PR A 1 Cl1 Cl 0.2986(7) 0.2568(4) 0.9894(2) 0.118(2) Uani 0.50 1 d PDU A 1 Cl2 Cl 0.0327(7) 0.2388(4) 0.9867(2) 0.109(2) Uani 0.50 1 d PDU A 1 C2S C 0.3209(10) 0.2717(16) 0.9438(5) 0.100 Uiso 0.50 1 d PD B 2 H2S1 H 0.3414 0.3298 0.9222 0.120 Uiso 0.50 1 calc PR B 2 H2S2 H 0.3252 0.2127 0.9213 0.120 Uiso 0.50 1 calc PR B 2 Cl3 Cl 0.1684(6) 0.2835(4) 0.9714(2) 0.108(2) Uani 0.50 1 d PDU B 2 Cl4 Cl 0.4286(7) 0.2616(4) 0.99664(19) 0.0980(19) Uani 0.50 1 d PDU B 2 O1 O 0.2354(4) 0.2025(2) 0.75644(13) 0.0301(8) Uani 1 1 d . . . O2 O 0.2380(4) 0.2716(2) 0.83556(15) 0.0385(10) Uani 1 1 d . . . O3 O 0.1920(3) -0.1569(2) 0.97699(13) 0.0286(8) Uani 1 1 d . . . O4 O 0.0694(4) 0.1775(3) 1.20771(13) 0.0341(9) Uani 1 1 d . . . O5 O 0.0400(3) 0.6460(2) 1.04908(12) 0.0274(8) Uani 1 1 d . . . O6 O -0.0485(3) 0.3924(2) 0.78867(12) 0.0234(7) Uani 1 1 d . . . O7 O -0.1294(4) -0.1122(2) 0.90990(12) 0.0277(8) Uani 1 1 d . . . O8 O -0.1650(3) -0.0418(2) 0.98873(12) 0.0253(8) Uani 1 1 d . . . N1 N 0.2020(4) 0.0926(3) 0.88174(16) 0.0234(9) Uani 1 1 d . . . N2 N 0.1702(4) 0.0059(3) 0.95676(16) 0.0265(9) Uani 1 1 d D . . H2N H 0.155(5) 0.064(2) 0.970(2) 0.032 Uiso 1 1 d D . . N3 N 0.1325(4) 0.0466(3) 1.05901(15) 0.0232(9) Uani 1 1 d . . . N4 N 0.0893(4) 0.1676(3) 1.11856(15) 0.0258(9) Uani 1 1 d D . . H4N H 0.094(5) 0.210(3) 1.0919(14) 0.031 Uiso 1 1 d D . . N5 N 0.0435(4) 0.3580(3) 1.10785(14) 0.0230(9) Uani 1 1 d . . . N6 N 0.0159(4) 0.4795(3) 1.04797(15) 0.0215(9) Uani 1 1 d D . . H6N H 0.011(5) 0.423(2) 1.0319(18) 0.026 Uiso 1 1 d D . . N7 N -0.0308(4) 0.4800(3) 0.94617(14) 0.0187(8) Uani 1 1 d . . . N8 N -0.0771(4) 0.3806(3) 0.87733(14) 0.0203(8) Uani 1 1 d D . . H8N H -0.104(5) 0.334(3) 0.8994(16) 0.024 Uiso 1 1 d D . . N9 N -0.1168(3) 0.1897(3) 0.87117(13) 0.0161(8) Uani 1 1 d . . . N10 N -0.1529(4) 0.0540(3) 0.92092(14) 0.0238(9) Uani 1 1 d D . . H10N H -0.181(5) 0.101(3) 0.9425(17) 0.029 Uiso 1 1 d D . . C1 C 0.2478(6) 0.3007(4) 0.7342(2) 0.0376(14) Uani 1 1 d . . . H1A H 0.3266 0.3308 0.7468 0.056 Uiso 1 1 calc R . . H1B H 0.1750 0.3407 0.7449 0.056 Uiso 1 1 calc R . . H1C H 0.2500 0.2962 0.6959 0.056 Uiso 1 1 calc R . . C2 C 0.2313(5) 0.2002(4) 0.8086(2) 0.0289(11) Uani 1 1 d . . . C3 C 0.2159(5) 0.0975(3) 0.8289(2) 0.0255(11) Uani 1 1 d . . . C4 C 0.2111(4) 0.0174(4) 0.7966(2) 0.0263(11) Uani 1 1 d . . . H4 H 0.2202 0.0238 0.7597 0.032 Uiso 1 1 calc R . . C5 C 0.1926(5) -0.0730(4) 0.81960(19) 0.0261(11) Uani 1 1 d . . . H5 H 0.1901 -0.1298 0.7982 0.031 Uiso 1 1 calc R . . C6 C 0.1778(4) -0.0826(3) 0.8724(2) 0.0254(11) Uani 1 1 d . . . H6 H 0.1636 -0.1445 0.8883 0.031 Uiso 1 1 calc R . . C7 C 0.1848(5) 0.0043(4) 0.9026(2) 0.0250(11) Uani 1 1 d . . . C8 C 0.1737(4) -0.0727(3) 0.99013(19) 0.0224(10) Uani 1 1 d . . . C9 C 0.1527(4) -0.0468(3) 1.04723(19) 0.0238(10) Uani 1 1 d . . . C10 C 0.1539(5) -0.1228(3) 1.08349(19) 0.0239(10) Uani 1 1 d . . . H10 H 0.1664 -0.1889 1.0731 0.029 Uiso 1 1 calc R . . C11 C 0.1358(5) -0.0973(4) 1.1354(2) 0.0286(11) Uani 1 1 d . . . H11 H 0.1385 -0.1466 1.1617 0.034 Uiso 1 1 calc R . . C12 C 0.1138(5) -0.0018(3) 1.1495(2) 0.0246(11) Uani 1 1 d . . . H12 H 0.0999 0.0158 1.1850 0.030 Uiso 1 1 calc R . . C13 C 0.1128(4) 0.0689(4) 1.10963(18) 0.0217(10) Uani 1 1 d . . . C14 C 0.0704(5) 0.2167(4) 1.1645(2) 0.0276(11) Uani 1 1 d . . . C15 C 0.0506(5) 0.3238(3) 1.15751(18) 0.0230(10) Uani 1 1 d . . . C16 C 0.0395(5) 0.3845(4) 1.20071(18) 0.0277(11) Uani 1 1 d . . . H16 H 0.0403 0.3582 1.2352 0.033 Uiso 1 1 calc R . . C17 C 0.0275(5) 0.4839(4) 1.19267(18) 0.0262(11) Uani 1 1 d . . . H17 H 0.0224 0.5269 1.2218 0.031 Uiso 1 1 calc R . . C18 C 0.0227(5) 0.5217(4) 1.14174(17) 0.0228(10) Uani 1 1 d . . . H18 H 0.0156 0.5900 1.1353 0.027 Uiso 1 1 calc R . . C19 C 0.0289(5) 0.4533(4) 1.10055(17) 0.0235(10) Uani 1 1 d . . . C20 C 0.0196(4) 0.5707(3) 1.02551(18) 0.0215(10) Uani 1 1 d . . . C21 C -0.0036(4) 0.5683(4) 0.96725(17) 0.0206(10) Uani 1 1 d . . . C22 C 0.0048(4) 0.6535(3) 0.93822(18) 0.0210(10) Uani 1 1 d . . . H22 H 0.0258 0.7143 0.9541 0.025 Uiso 1 1 calc R . . C23 C -0.0187(5) 0.6465(3) 0.88510(19) 0.0244(10) Uani 1 1 d . . . H23 H -0.0156 0.7037 0.8640 0.029 Uiso 1 1 calc R . . C24 C -0.0465(4) 0.5583(3) 0.86240(17) 0.0206(10) Uani 1 1 d . . . H24 H -0.0627 0.5533 0.8259 0.025 Uiso 1 1 calc R . . C25 C -0.0501(4) 0.4761(3) 0.89480(17) 0.0197(10) Uani 1 1 d . . . C26 C -0.0704(4) 0.3436(3) 0.82761(17) 0.0183(9) Uani 1 1 d . . . C27 C -0.0909(4) 0.2352(3) 0.82540(16) 0.0151(9) Uani 1 1 d . . . C28 C -0.0772(4) 0.1851(3) 0.77879(17) 0.0202(10) Uani 1 1 d . . . H28 H -0.0600 0.2187 0.7470 0.024 Uiso 1 1 calc R . . C29 C -0.0896(4) 0.0841(3) 0.78011(16) 0.0186(9) Uani 1 1 d . . . H29 H -0.0811 0.0478 0.7486 0.022 Uiso 1 1 calc R . . C30 C -0.1141(4) 0.0354(3) 0.82637(17) 0.0172(9) Uani 1 1 d . . . H30 H -0.1212 -0.0339 0.8277 0.021 Uiso 1 1 calc R . . C31 C -0.1280(4) 0.0937(3) 0.87126(16) 0.0178(9) Uani 1 1 d . . . C32 C -0.1471(4) -0.0411(3) 0.93649(17) 0.0195(9) Uani 1 1 d . . . C33 C -0.1599(5) -0.1363(3) 1.01440(16) 0.0177(9) Uani 1 1 d . . . H33A H -0.0775 -0.1688 1.0072 0.021 Uiso 1 1 calc R . . H33B H -0.2293 -0.1790 1.0016 0.021 Uiso 1 1 calc R . . C34 C -0.1746(4) -0.1175(3) 1.07234(18) 0.0196(10) Uani 1 1 d . . . C35 C -0.1557(4) -0.1947(3) 1.10695(17) 0.0202(10) Uani 1 1 d . . . H35 H -0.1342 -0.2577 1.0939 0.024 Uiso 1 1 calc R . . C36 C -0.1680(5) -0.1800(4) 1.16080(18) 0.0258(11) Uani 1 1 d . . . H36 H -0.1549 -0.2330 1.1843 0.031 Uiso 1 1 calc R . . C37 C -0.1993(5) -0.0887(4) 1.17997(18) 0.0288(12) Uani 1 1 d . . . H37 H -0.2071 -0.0791 1.2167 0.035 Uiso 1 1 calc R . . C38 C -0.2193(6) -0.0116(4) 1.1466(2) 0.0358(13) Uani 1 1 d . . . H38 H -0.2419 0.0509 1.1599 0.043 Uiso 1 1 calc R . . C39 C -0.2059(5) -0.0263(4) 1.0920(2) 0.0320(12) Uani 1 1 d . . . H39 H -0.2186 0.0270 1.0686 0.038 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 0.181(6) 0.074(3) 0.099(4) -0.024(3) -0.007(4) 0.016(4) Cl2 0.200(6) 0.051(2) 0.075(3) 0.009(2) -0.062(4) -0.014(4) Cl3 0.159(5) 0.057(3) 0.108(4) 0.011(3) 0.052(4) 0.044(3) Cl4 0.187(6) 0.063(3) 0.044(2) -0.0133(19) 0.002(3) 0.009(4) O1 0.041(2) 0.0221(18) 0.0274(19) 0.0086(15) 0.0068(16) 0.0054(16) O2 0.062(3) 0.0206(18) 0.033(2) 0.0116(16) 0.0003(19) 0.0002(18) O3 0.042(2) 0.0174(17) 0.0263(18) 0.0035(14) -0.0051(16) 0.0009(15) O4 0.044(2) 0.035(2) 0.0228(19) 0.0038(16) -0.0040(16) 0.0042(18) O5 0.042(2) 0.0195(17) 0.0205(17) -0.0070(13) 0.0038(16) -0.0055(16) O6 0.038(2) 0.0183(16) 0.0143(15) 0.0008(12) 0.0000(14) 0.0015(15) O7 0.051(2) 0.0203(17) 0.0114(15) 0.0000(13) 0.0063(15) 0.0037(16) O8 0.043(2) 0.0184(16) 0.0150(16) 0.0022(12) 0.0057(14) -0.0067(15) N1 0.022(2) 0.020(2) 0.028(2) 0.0011(17) 0.0025(17) 0.0047(17) N2 0.033(2) 0.018(2) 0.029(2) 0.0038(17) 0.0026(19) 0.0014(18) N3 0.021(2) 0.023(2) 0.026(2) 0.0040(16) 0.0006(16) 0.0019(16) N4 0.032(2) 0.024(2) 0.021(2) 0.0033(16) 0.0086(18) 0.0055(18) N5 0.023(2) 0.029(2) 0.0175(19) -0.0066(16) 0.0022(16) 0.0018(18) N6 0.031(2) 0.0162(19) 0.0176(19) -0.0059(15) 0.0002(17) 0.0022(17) N7 0.024(2) 0.0151(18) 0.0170(19) -0.0036(14) 0.0047(16) 0.0022(16) N8 0.033(2) 0.0150(19) 0.0131(18) -0.0006(14) 0.0042(16) -0.0052(16) N9 0.0178(19) 0.0177(18) 0.0129(17) -0.0011(14) -0.0040(14) -0.0028(15) N10 0.042(3) 0.0166(19) 0.0130(19) -0.0026(15) 0.0066(17) -0.0015(18) C1 0.053(4) 0.025(3) 0.034(3) 0.020(2) 0.010(3) 0.004(3) C2 0.029(3) 0.025(3) 0.032(3) 0.008(2) -0.002(2) 0.001(2) C3 0.019(2) 0.028(3) 0.030(3) 0.008(2) -0.001(2) 0.003(2) C4 0.018(2) 0.030(3) 0.031(3) 0.006(2) -0.006(2) 0.003(2) C5 0.025(3) 0.025(2) 0.029(3) 0.000(2) -0.008(2) -0.001(2) C6 0.017(2) 0.023(2) 0.037(3) 0.009(2) 0.000(2) 0.0019(19) C7 0.019(2) 0.025(2) 0.031(3) 0.005(2) 0.001(2) 0.005(2) C8 0.018(2) 0.017(2) 0.032(3) 0.0020(19) -0.002(2) -0.0005(19) C9 0.016(2) 0.028(3) 0.028(3) 0.000(2) 0.004(2) 0.000(2) C10 0.030(3) 0.014(2) 0.028(3) -0.0055(18) 0.000(2) 0.002(2) C11 0.025(3) 0.031(3) 0.030(3) 0.007(2) -0.004(2) -0.002(2) C12 0.021(2) 0.025(3) 0.028(3) 0.000(2) 0.000(2) 0.002(2) C13 0.013(2) 0.027(2) 0.025(2) -0.0013(19) -0.0002(18) 0.0027(19) C14 0.022(3) 0.032(3) 0.029(3) 0.001(2) 0.001(2) 0.006(2) C15 0.019(2) 0.029(3) 0.021(2) 0.0064(19) -0.0024(19) 0.004(2) C16 0.032(3) 0.036(3) 0.015(2) 0.002(2) -0.006(2) 0.006(2) C17 0.027(3) 0.036(3) 0.016(2) -0.008(2) -0.0009(19) -0.002(2) C18 0.024(2) 0.027(3) 0.017(2) -0.0041(19) -0.0020(19) 0.000(2) C19 0.024(3) 0.028(3) 0.018(2) -0.0059(19) 0.0056(19) 0.001(2) C20 0.021(2) 0.024(2) 0.020(2) -0.0024(19) 0.0006(19) 0.001(2) C21 0.018(2) 0.028(2) 0.016(2) -0.0014(18) 0.0012(17) -0.0008(19) C22 0.022(2) 0.014(2) 0.027(2) -0.0046(18) 0.0047(19) -0.0029(18) C23 0.030(3) 0.016(2) 0.027(3) 0.0013(19) 0.005(2) 0.002(2) C24 0.025(2) 0.023(2) 0.015(2) -0.0032(18) 0.0016(19) -0.001(2) C25 0.022(2) 0.019(2) 0.018(2) -0.0029(18) 0.0036(19) -0.0022(19) C26 0.021(2) 0.017(2) 0.016(2) 0.0026(17) -0.0040(18) 0.0005(18) C27 0.012(2) 0.019(2) 0.014(2) 0.0038(17) 0.0019(16) 0.0026(17) C28 0.021(2) 0.028(2) 0.012(2) 0.0057(18) -0.0014(17) 0.002(2) C29 0.024(2) 0.021(2) 0.010(2) -0.0097(17) 0.0008(17) 0.0000(19) C30 0.016(2) 0.015(2) 0.020(2) -0.0053(17) -0.0033(18) -0.0017(17) C31 0.019(2) 0.024(2) 0.011(2) -0.0006(17) -0.0017(17) -0.0002(18) C32 0.017(2) 0.023(2) 0.018(2) 0.0019(19) 0.0001(18) -0.0018(19) C33 0.029(3) 0.0075(19) 0.017(2) 0.0027(16) 0.0040(18) -0.0030(18) C34 0.022(2) 0.018(2) 0.019(2) 0.0009(17) 0.0029(18) -0.0008(18) C35 0.021(2) 0.017(2) 0.022(2) -0.0004(18) -0.0036(19) -0.0032(19) C36 0.030(3) 0.031(3) 0.017(2) 0.003(2) 0.005(2) -0.009(2) C37 0.030(3) 0.044(3) 0.012(2) -0.001(2) 0.002(2) -0.006(2) C38 0.055(4) 0.026(3) 0.026(3) -0.007(2) 0.011(3) 0.007(3) C39 0.043(3) 0.027(3) 0.025(3) 0.004(2) 0.002(2) 0.000(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1S Cl1 1.767(10) . ? C1S Cl2 1.781(10) . ? C2S Cl3 1.758(10) . ? C2S Cl4 1.767(10) . ? O1 C2 1.333(6) . ? O1 C1 1.463(6) . ? O2 C2 1.197(6) . ? O3 C8 1.213(6) . ? O4 C14 1.227(6) . ? O5 C20 1.211(5) . ? O6 C26 1.219(5) . ? O7 C32 1.199(5) . ? O8 C32 1.347(5) . ? O8 C33 1.449(5) . ? N1 C7 1.331(6) . ? N1 C3 1.359(6) . ? N2 C8 1.371(6) . ? N2 C7 1.392(6) . ? N3 C9 1.328(6) . ? N3 C13 1.344(6) . ? N4 C14 1.366(6) . ? N4 C13 1.391(6) . ? N5 C19 1.324(6) . ? N5 C15 1.353(6) . ? N6 C20 1.373(6) . ? N6 C19 1.396(6) . ? N7 C25 1.329(6) . ? N7 C21 1.351(6) . ? N8 C26 1.368(6) . ? N8 C25 1.408(6) . ? N9 C31 1.318(6) . ? N9 C27 1.352(5) . ? N10 C32 1.360(6) . ? N10 C31 1.404(5) . ? C2 C3 1.504(7) . ? C3 C4 1.372(7) . ? C4 C5 1.381(7) . ? C5 C6 1.365(7) . ? C6 C7 1.417(7) . ? C8 C9 1.517(7) . ? C9 C10 1.391(7) . ? C10 C11 1.384(7) . ? C11 C12 1.373(7) . ? C12 C13 1.403(7) . ? C14 C15 1.488(7) . ? C15 C16 1.385(7) . ? C16 C17 1.379(7) . ? C17 C18 1.401(7) . ? C18 C19 1.409(6) . ? C20 C21 1.508(6) . ? C21 C22 1.383(6) . ? C22 C23 1.382(7) . ? C23 C24 1.368(6) . ? C24 C25 1.396(6) . ? C26 C27 1.497(6) . ? C27 C28 1.380(6) . ? C28 C29 1.387(6) . ? C29 C30 1.380(6) . ? C30 C31 1.403(6) . ? C33 C34 1.510(6) . ? C34 C39 1.383(7) . ? C34 C35 1.391(6) . ? C35 C36 1.396(6) . ? C36 C37 1.380(7) . ? C37 C38 1.371(7) . ? C38 C39 1.415(7) . ? 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 Cl1 C1S Cl2 104.6(7) . . ? Cl3 C2S Cl4 106.5(7) . . ? C2 O1 C1 114.4(4) . . ? C32 O8 C33 116.7(3) . . ? C7 N1 C3 117.2(4) . . ? C8 N2 C7 127.1(4) . . ? C9 N3 C13 117.4(4) . . ? C14 N4 C13 130.0(4) . . ? C19 N5 C15 118.5(4) . . ? C20 N6 C19 129.2(4) . . ? C25 N7 C21 117.5(4) . . ? C26 N8 C25 128.7(4) . . ? C31 N9 C27 118.5(4) . . ? C32 N10 C31 128.6(4) . . ? O2 C2 O1 123.6(5) . . ? O2 C2 C3 124.7(5) . . ? O1 C2 C3 111.7(4) . . ? N1 C3 C4 123.7(4) . . ? N1 C3 C2 113.6(4) . . ? C4 C3 C2 122.7(5) . . ? C3 C4 C5 117.5(5) . . ? C6 C5 C4 121.5(5) . . ? C5 C6 C7 116.8(4) . . ? N1 C7 N2 113.5(4) . . ? N1 C7 C6 123.3(5) . . ? N2 C7 C6 123.1(4) . . ? O3 C8 N2 125.1(5) . . ? O3 C8 C9 120.7(4) . . ? N2 C8 C9 114.2(4) . . ? N3 C9 C10 124.6(4) . . ? N3 C9 C8 117.7(4) . . ? C10 C9 C8 117.7(4) . . ? C11 C10 C9 116.6(4) . . ? C12 C11 C10 120.9(5) . . ? C11 C12 C13 117.7(5) . . ? N3 C13 N4 113.9(4) . . ? N3 C13 C12 122.7(4) . . ? N4 C13 C12 123.4(4) . . ? O4 C14 N4 124.0(5) . . ? O4 C14 C15 122.5(5) . . ? N4 C14 C15 113.5(4) . . ? N5 C15 C16 122.4(4) . . ? N5 C15 C14 117.4(4) . . ? C16 C15 C14 120.3(4) . . ? C17 C16 C15 118.6(4) . . ? C16 C17 C18 120.3(4) . . ? C17 C18 C19 116.5(4) . . ? N5 C19 N6 113.5(4) . . ? N5 C19 C18 123.6(4) . . ? N6 C19 C18 122.9(4) . . ? O5 C20 N6 124.7(4) . . ? O5 C20 C21 122.5(4) . . ? N6 C20 C21 112.8(4) . . ? N7 C21 C22 123.5(4) . . ? N7 C21 C20 116.5(4) . . ? C22 C21 C20 120.0(4) . . ? C23 C22 C21 117.1(4) . . ? C24 C23 C22 121.0(4) . . ? C23 C24 C25 117.6(4) . . ? N7 C25 C24 123.3(4) . . ? N7 C25 N8 112.4(4) . . ? C24 C25 N8 124.3(4) . . ? O6 C26 N8 124.4(4) . . ? O6 C26 C27 122.5(4) . . ? N8 C26 C27 113.1(4) . . ? N9 C27 C28 122.6(4) . . ? N9 C27 C26 116.8(4) . . ? C28 C27 C26 120.5(4) . . ? C27 C28 C29 117.6(4) . . ? C30 C29 C28 121.2(4) . . ? C29 C30 C31 116.4(4) . . ? N9 C31 C30 123.7(4) . . ? N9 C31 N10 113.8(4) . . ? C30 C31 N10 122.6(4) . . ? O7 C32 O8 125.2(4) . . ? O7 C32 N10 127.9(4) . . ? O8 C32 N10 106.8(4) . . ? O8 C33 C34 106.7(3) . . ? C39 C34 C35 119.2(4) . . ? C39 C34 C33 122.2(4) . . ? C35 C34 C33 118.6(4) . . ? C34 C35 C36 120.2(4) . . ? C37 C36 C35 120.1(5) . . ? C38 C37 C36 120.7(4) . . ? C37 C38 C39 119.3(5) . . ? C34 C39 C38 120.6(5) . . ? 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 N10 H10N Cl4 0.90(2) 2.69(4) 3.393(6) 136(4) 4_457 N10 H10N Cl1 0.90(2) 2.61(2) 3.491(7) 166(4) 4_457 N8 H8N Cl4 0.89(2) 2.98(3) 3.760(6) 147(4) 4_457 N8 H8N Cl2 0.89(2) 2.96(4) 3.589(6) 130(4) . N8 H8N N9 0.89(2) 2.11(5) 2.645(5) 118(4) . N6 H6N Cl3 0.88(2) 2.96(4) 3.682(6) 141(4) . N6 H6N Cl2 0.88(2) 2.78(2) 3.646(7) 171(4) . N6 H6N Cl4 0.88(2) 2.76(3) 3.604(7) 161(4) 4_457 N4 H4N Cl4 0.90(2) 2.88(4) 3.527(7) 130(4) 4_457 N4 H4N Cl2 0.90(2) 2.79(4) 3.555(7) 144(4) . N4 H4N N5 0.90(2) 2.13(5) 2.659(6) 117(4) . N2 H2N Cl2 0.88(2) 2.75(3) 3.578(7) 158(5) . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.458 _refine_diff_density_min -0.901 _refine_diff_density_rms 0.098 data_a384 _database_code_depnum_ccdc_archive 'CCDC 838393' #TrackingRef 'web_deposit_cif_file_2_OngWeiQiang_1312792022.A384.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H32 Cl2 N10 O8' _chemical_formula_weight 851.66 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 P2(1)2(1)2(1) 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' _cell_length_a 10.5003(13) _cell_length_b 13.6695(17) _cell_length_c 25.510(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3661.5(8) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 928 _cell_measurement_theta_min 2.57 _cell_measurement_theta_max 25.72 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.545 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1760 _exptl_absorpt_coefficient_mu 0.250 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9065 _exptl_absorpt_correction_T_max 0.9610 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25780 _diffrn_reflns_av_R_equivalents 0.0407 _diffrn_reflns_av_sigmaI/netI 0.0479 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 27.50 _reflns_number_total 8402 _reflns_number_gt 7226 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0827P)^2^+3.0303P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.08(18) _refine_ls_number_reflns 8402 _refine_ls_number_parameters 572 _refine_ls_number_restraints 35 _refine_ls_R_factor_all 0.0764 _refine_ls_R_factor_gt 0.0641 _refine_ls_wR_factor_ref 0.1665 _refine_ls_wR_factor_gt 0.1579 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.123 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1S C 0.8362(10) 0.7093(17) 0.0475(7) 0.100 Uiso 0.50 1 d PD A 1 H1S1 H 0.8442 0.6373 0.0496 0.120 Uiso 0.50 1 calc PR A 1 H1S2 H 0.8305 0.7360 0.0835 0.120 Uiso 0.50 1 calc PR A 1 Cl1 Cl 0.7019(6) 0.7427(3) 0.01044(16) 0.1167(17) Uani 0.50 1 d PDU A 1 Cl2 Cl 0.9686(6) 0.7612(2) 0.01332(15) 0.1134(19) Uani 0.50 1 d PDU A 1 C2S C 0.6805(9) 0.7288(13) 0.0545(5) 0.100 Uiso 0.50 1 d PD B 2 H2S1 H 0.6763 0.7882 0.0767 0.120 Uiso 0.50 1 calc PR B 2 H2S2 H 0.6607 0.6715 0.0768 0.120 Uiso 0.50 1 calc PR B 2 Cl3 Cl 0.8328(5) 0.7168(3) 0.02839(18) 0.122(2) Uani 0.50 1 d PDU B 2 Cl4 Cl 0.5689(7) 0.7375(3) 0.00361(15) 0.1095(19) Uani 0.50 1 d PDU B 2 O1 O 0.7642(3) 0.79776(18) 0.24377(10) 0.0322(6) Uani 1 1 d . . . O2 O 0.7622(3) 0.72822(19) 0.16417(12) 0.0410(7) Uani 1 1 d . . . O3 O 0.8084(3) 1.15662(18) 0.02334(10) 0.0330(6) Uani 1 1 d . . . O4 O 0.9316(3) 0.8222(2) -0.20792(10) 0.0374(6) Uani 1 1 d . . . O5 O 0.9593(3) 0.35452(17) -0.04924(9) 0.0312(6) Uani 1 1 d . . . O6 O 1.0483(3) 0.60778(17) 0.21137(9) 0.0282(5) Uani 1 1 d . . . O7 O 1.1294(3) 1.11153(17) 0.09044(9) 0.0309(6) Uani 1 1 d . . . O8 O 1.1658(3) 1.04216(16) 0.01152(9) 0.0282(5) Uani 1 1 d . . . N1 N 0.7980(3) 0.9078(2) 0.11842(12) 0.0253(6) Uani 1 1 d . . . N2 N 0.8303(3) 0.9944(2) 0.04308(12) 0.0283(6) Uani 1 1 d D . . H2N H 0.834(4) 0.9370(19) 0.0280(15) 0.034 Uiso 1 1 d D . . N3 N 0.8678(3) 0.9538(2) -0.05925(11) 0.0248(6) Uani 1 1 d . . . N4 N 0.9105(3) 0.8323(2) -0.11852(11) 0.0288(6) Uani 1 1 d D . . H4N H 0.911(4) 0.788(2) -0.0936(13) 0.035 Uiso 1 1 d D . . N5 N 0.9557(3) 0.6423(2) -0.10814(11) 0.0242(6) Uani 1 1 d . . . N6 N 0.9848(3) 0.5209(2) -0.04806(11) 0.0228(6) Uani 1 1 d D . . H6N H 0.998(4) 0.575(2) -0.0297(14) 0.027 Uiso 1 1 d D . . N7 N 1.0314(3) 0.52002(19) 0.05364(10) 0.0214(5) Uani 1 1 d . . . N8 N 1.0776(3) 0.61934(19) 0.12264(11) 0.0225(6) Uani 1 1 d D . . H8N H 1.093(4) 0.664(2) 0.0978(12) 0.027 Uiso 1 1 d D . . N9 N 1.1179(3) 0.80993(19) 0.12896(10) 0.0190(5) Uani 1 1 d . . . N10 N 1.1531(3) 0.9455(2) 0.07939(10) 0.0255(6) Uani 1 1 d D . . H10N H 1.171(4) 0.900(2) 0.0567(13) 0.031 Uiso 1 1 d D . . C1 C 0.7520(4) 0.7000(3) 0.26568(16) 0.0389(9) Uani 1 1 d . . . H1A H 0.6691 0.6725 0.2559 0.058 Uiso 1 1 calc R . . H1B H 0.7585 0.7034 0.3040 0.058 Uiso 1 1 calc R . . H1C H 0.8201 0.6582 0.2519 0.058 Uiso 1 1 calc R . . C2 C 0.7688(3) 0.7996(3) 0.19150(15) 0.0292(8) Uani 1 1 d . . . C3 C 0.7845(3) 0.9023(2) 0.17086(14) 0.0261(7) Uani 1 1 d . . . C4 C 0.7886(3) 0.9828(3) 0.20368(14) 0.0272(7) Uani 1 1 d . . . H4 H 0.7789 0.9760 0.2405 0.033 Uiso 1 1 calc R . . C5 C 0.8073(3) 1.0739(3) 0.18088(14) 0.0284(7) Uani 1 1 d . . . H5 H 0.8106 1.1307 0.2022 0.034 Uiso 1 1 calc R . . C6 C 0.8210(3) 1.0820(2) 0.12764(15) 0.0279(7) Uani 1 1 d . . . H6 H 0.8342 1.1439 0.1116 0.033 Uiso 1 1 calc R . . C7 C 0.8151(3) 0.9958(3) 0.09719(14) 0.0263(7) Uani 1 1 d . . . C8 C 0.8266(3) 1.0728(2) 0.00971(14) 0.0247(7) Uani 1 1 d . . . C9 C 0.8471(3) 1.0469(3) -0.04726(14) 0.0252(7) Uani 1 1 d . . . C10 C 0.8459(3) 1.1233(2) -0.08396(14) 0.0273(7) Uani 1 1 d . . . H10 H 0.8326 1.1893 -0.0737 0.033 Uiso 1 1 calc R . . C11 C 0.8649(3) 1.0981(3) -0.13544(15) 0.0306(8) Uani 1 1 d . . . H11 H 0.8631 1.1474 -0.1617 0.037 Uiso 1 1 calc R . . C12 C 0.8865(3) 1.0017(3) -0.14963(14) 0.0287(7) Uani 1 1 d . . . H12 H 0.9003 0.9838 -0.1852 0.034 Uiso 1 1 calc R . . C13 C 0.8873(3) 0.9316(3) -0.10946(14) 0.0263(7) Uani 1 1 d . . . C14 C 0.9296(3) 0.7845(3) -0.16458(14) 0.0285(7) Uani 1 1 d . . . C15 C 0.9499(3) 0.6758(3) -0.15741(13) 0.0252(7) Uani 1 1 d . . . C16 C 0.9600(3) 0.6158(3) -0.20095(14) 0.0292(7) Uani 1 1 d . . . H16 H 0.9584 0.6420 -0.2354 0.035 Uiso 1 1 calc R . . C17 C 0.9724(3) 0.5158(3) -0.19241(13) 0.0291(8) Uani 1 1 d . . . H17 H 0.9779 0.4725 -0.2214 0.035 Uiso 1 1 calc R . . C18 C 0.9768(3) 0.4792(3) -0.14224(13) 0.0251(7) Uani 1 1 d . . . H18 H 0.9833 0.4109 -0.1359 0.030 Uiso 1 1 calc R . . C19 C 0.9713(3) 0.5464(2) -0.10065(13) 0.0232(7) Uani 1 1 d . . . C20 C 0.9803(3) 0.4301(2) -0.02579(13) 0.0237(7) Uani 1 1 d . . . C21 C 1.0038(3) 0.4323(2) 0.03249(13) 0.0221(6) Uani 1 1 d . . . C22 C 0.9958(3) 0.3463(2) 0.06155(14) 0.0248(7) Uani 1 1 d . . . H22 H 0.9754 0.2856 0.0455 0.030 Uiso 1 1 calc R . . C23 C 1.0189(3) 0.3531(2) 0.11481(13) 0.0255(7) Uani 1 1 d . . . H23 H 1.0155 0.2958 0.1359 0.031 Uiso 1 1 calc R . . C24 C 1.0467(3) 0.4419(2) 0.13775(13) 0.0247(7) Uani 1 1 d . . . H24 H 1.0627 0.4471 0.1743 0.030 Uiso 1 1 calc R . . C25 C 1.0506(3) 0.5244(2) 0.10489(12) 0.0217(6) Uani 1 1 d . . . C26 C 1.0711(3) 0.6558(2) 0.17248(12) 0.0206(6) Uani 1 1 d . . . C27 C 1.0917(3) 0.7650(2) 0.17446(12) 0.0185(6) Uani 1 1 d . . . C28 C 1.0773(3) 0.8147(2) 0.22166(12) 0.0209(6) Uani 1 1 d . . . H28 H 1.0607 0.7809 0.2535 0.025 Uiso 1 1 calc R . . C29 C 1.0882(3) 0.9165(2) 0.22018(12) 0.0219(6) Uani 1 1 d . . . H29 H 1.0779 0.9532 0.2515 0.026 Uiso 1 1 calc R . . C30 C 1.1137(3) 0.9642(2) 0.17400(12) 0.0204(6) Uani 1 1 d . . . H30 H 1.1216 1.0334 0.1727 0.024 Uiso 1 1 calc R . . C31 C 1.1278(3) 0.9066(2) 0.12888(12) 0.0190(6) Uani 1 1 d . . . C32 C 1.1478(3) 1.0408(2) 0.06351(12) 0.0211(6) Uani 1 1 d . . . C33 C 1.1606(3) 1.1362(2) -0.01446(12) 0.0222(6) Uani 1 1 d . . . H33A H 1.2303 1.1788 -0.0018 0.027 Uiso 1 1 calc R . . H33B H 1.0784 1.1688 -0.0071 0.027 Uiso 1 1 calc R . . C34 C 1.1747(3) 1.1177(2) -0.07229(12) 0.0213(6) Uani 1 1 d . . . C35 C 1.1559(3) 1.1950(2) -0.10697(12) 0.0240(7) Uani 1 1 d . . . H35 H 1.1343 1.2579 -0.0939 0.029 Uiso 1 1 calc R . . C36 C 1.1684(3) 1.1807(3) -0.16062(13) 0.0277(7) Uani 1 1 d . . . H36 H 1.1557 1.2338 -0.1841 0.033 Uiso 1 1 calc R . . C37 C 1.1996(3) 1.0890(3) -0.17997(13) 0.0299(8) Uani 1 1 d . . . H37 H 1.2081 1.0793 -0.2167 0.036 Uiso 1 1 calc R . . C38 C 1.2183(4) 1.0119(3) -0.14595(15) 0.0349(9) Uani 1 1 d . . . H38 H 1.2401 0.9492 -0.1593 0.042 Uiso 1 1 calc R . . C39 C 1.2053(4) 1.0256(3) -0.09211(14) 0.0320(8) Uani 1 1 d . . . H39 H 1.2174 0.9722 -0.0688 0.038 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 0.217(5) 0.061(2) 0.073(2) -0.0222(17) -0.018(3) 0.021(3) Cl2 0.245(6) 0.0349(14) 0.061(2) 0.0096(15) -0.071(3) -0.017(3) Cl3 0.201(5) 0.0498(19) 0.115(3) 0.015(2) 0.072(3) 0.054(3) Cl4 0.228(6) 0.060(2) 0.0413(18) -0.0108(15) -0.002(3) 0.015(3) O1 0.0420(15) 0.0225(12) 0.0322(13) 0.0100(10) 0.0067(11) 0.0046(11) O2 0.0611(19) 0.0230(13) 0.0390(15) 0.0089(12) -0.0012(14) 0.0002(12) O3 0.0487(16) 0.0194(12) 0.0308(13) 0.0044(10) -0.0035(12) 0.0013(11) O4 0.0497(16) 0.0349(15) 0.0276(13) 0.0070(11) -0.0022(12) 0.0042(12) O5 0.0474(15) 0.0215(12) 0.0246(12) -0.0079(10) 0.0034(11) -0.0065(11) O6 0.0471(15) 0.0198(11) 0.0178(11) 0.0035(9) 0.0004(10) -0.0008(11) O7 0.0530(16) 0.0207(12) 0.0190(12) -0.0015(9) 0.0066(11) 0.0030(11) O8 0.0485(15) 0.0183(11) 0.0179(11) 0.0013(9) 0.0047(10) -0.0053(10) N1 0.0227(14) 0.0210(14) 0.0323(16) 0.0059(12) 0.0030(11) 0.0024(11) N2 0.0339(16) 0.0202(14) 0.0309(16) 0.0034(12) 0.0015(13) 0.0014(12) N3 0.0237(13) 0.0203(14) 0.0303(15) 0.0039(11) 0.0019(11) 0.0021(11) N4 0.0352(16) 0.0249(15) 0.0262(15) 0.0067(12) 0.0063(12) 0.0054(12) N5 0.0220(13) 0.0285(15) 0.0223(13) -0.0029(11) 0.0023(11) 0.0021(12) N6 0.0317(15) 0.0167(13) 0.0202(13) -0.0073(10) 0.0020(11) 0.0007(11) N7 0.0294(14) 0.0162(12) 0.0185(13) -0.0018(10) 0.0039(11) 0.0002(11) N8 0.0364(16) 0.0149(13) 0.0161(13) 0.0016(10) 0.0046(11) -0.0036(11) N9 0.0260(13) 0.0170(12) 0.0141(12) -0.0023(10) -0.0019(10) -0.0008(10) N10 0.0435(17) 0.0175(13) 0.0156(13) -0.0038(10) 0.0040(12) -0.0021(12) C1 0.054(3) 0.0242(19) 0.038(2) 0.0140(16) 0.0105(18) 0.0047(17) C2 0.0286(17) 0.0220(17) 0.037(2) 0.0091(15) 0.0016(15) 0.0022(14) C3 0.0199(15) 0.0231(16) 0.0352(19) 0.0096(14) -0.0008(14) 0.0027(13) C4 0.0263(16) 0.0276(18) 0.0276(17) 0.0075(14) -0.0020(14) 0.0015(14) C5 0.0309(18) 0.0224(16) 0.0319(18) -0.0001(14) -0.0072(14) 0.0008(14) C6 0.0279(17) 0.0173(15) 0.0385(19) 0.0093(14) -0.0043(14) -0.0003(13) C7 0.0180(15) 0.0257(17) 0.0352(19) 0.0076(14) 0.0013(13) 0.0027(13) C8 0.0217(15) 0.0199(15) 0.0323(18) 0.0032(13) -0.0010(13) -0.0004(13) C9 0.0155(14) 0.0270(17) 0.0331(18) 0.0024(14) 0.0013(13) -0.0026(13) C10 0.0292(17) 0.0182(16) 0.0345(19) 0.0041(13) -0.0051(14) 0.0008(13) C11 0.0274(17) 0.0306(18) 0.034(2) 0.0119(15) -0.0040(15) -0.0004(14) C12 0.0268(17) 0.0293(18) 0.0300(18) 0.0017(14) -0.0009(14) 0.0019(14) C13 0.0193(15) 0.0269(17) 0.0327(18) 0.0035(14) 0.0025(13) 0.0039(13) C14 0.0218(16) 0.0316(19) 0.0322(18) 0.0017(15) -0.0025(14) 0.0027(13) C15 0.0193(15) 0.0302(18) 0.0262(16) 0.0012(14) 0.0018(13) 0.0013(13) C16 0.0313(18) 0.035(2) 0.0211(16) 0.0015(14) -0.0016(14) -0.0016(15) C17 0.0299(18) 0.036(2) 0.0216(16) -0.0080(14) 0.0013(14) -0.0018(15) C18 0.0266(16) 0.0241(17) 0.0244(16) -0.0061(13) 0.0005(13) 0.0006(13) C19 0.0223(15) 0.0250(17) 0.0223(15) -0.0028(13) 0.0021(13) 0.0023(13) C20 0.0236(15) 0.0232(16) 0.0241(16) -0.0040(13) 0.0038(13) 0.0003(13) C21 0.0240(15) 0.0196(15) 0.0227(16) -0.0033(12) 0.0026(12) -0.0008(12) C22 0.0288(17) 0.0149(15) 0.0308(17) -0.0058(13) 0.0046(13) -0.0026(12) C23 0.0317(17) 0.0166(15) 0.0282(17) 0.0028(13) 0.0057(14) 0.0024(13) C24 0.0289(17) 0.0259(17) 0.0194(15) 0.0011(13) 0.0017(13) -0.0001(13) C25 0.0259(16) 0.0171(15) 0.0221(15) -0.0020(12) 0.0071(13) -0.0018(12) C26 0.0224(14) 0.0191(15) 0.0203(15) -0.0009(12) -0.0003(12) 0.0007(12) C27 0.0209(15) 0.0195(15) 0.0150(14) 0.0001(11) -0.0009(11) -0.0016(11) C28 0.0255(15) 0.0227(16) 0.0146(14) 0.0019(12) 0.0015(12) 0.0005(12) C29 0.0279(16) 0.0225(16) 0.0154(14) -0.0075(12) -0.0011(12) 0.0004(13) C30 0.0233(15) 0.0148(14) 0.0231(16) -0.0029(12) -0.0029(12) 0.0004(11) C31 0.0196(14) 0.0230(15) 0.0144(14) -0.0023(12) -0.0011(11) 0.0002(12) C32 0.0225(15) 0.0194(15) 0.0213(15) 0.0035(12) -0.0023(12) -0.0054(12) C33 0.0288(16) 0.0185(15) 0.0194(15) 0.0058(12) 0.0018(12) -0.0005(13) C34 0.0237(15) 0.0204(15) 0.0197(15) -0.0004(12) 0.0024(12) -0.0036(12) C35 0.0288(17) 0.0203(15) 0.0229(16) 0.0007(12) -0.0007(13) -0.0021(13) C36 0.0304(17) 0.0294(18) 0.0233(16) 0.0087(14) 0.0025(13) -0.0055(14) C37 0.0332(18) 0.042(2) 0.0147(15) -0.0026(14) 0.0042(13) -0.0064(15) C38 0.049(2) 0.0281(19) 0.0275(18) -0.0063(15) 0.0065(16) 0.0036(17) C39 0.050(2) 0.0207(17) 0.0252(17) 0.0024(13) 0.0026(16) 0.0040(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 C1S Cl1 1.759(10) . ? C1S Cl2 1.788(10) . ? C2S Cl3 1.740(9) . ? C2S Cl4 1.754(9) . ? O1 C2 1.334(4) . ? O1 C1 1.454(4) . ? O2 C2 1.201(5) . ? O3 C8 1.212(4) . ? O4 C14 1.220(4) . ? O5 C20 1.214(4) . ? O6 C26 1.213(4) . ? O7 C32 1.202(4) . ? O8 C32 1.340(4) . ? O8 C33 1.447(4) . ? N1 C7 1.331(4) . ? N1 C3 1.347(5) . ? N2 C8 1.369(4) . ? N2 C7 1.390(5) . ? N3 C9 1.328(4) . ? N3 C13 1.332(5) . ? N4 C14 1.360(5) . ? N4 C13 1.398(5) . ? N5 C19 1.335(4) . ? N5 C15 1.339(4) . ? N6 C20 1.366(4) . ? N6 C19 1.393(4) . ? N7 C25 1.324(4) . ? N7 C21 1.346(4) . ? N8 C26 1.367(4) . ? N8 C25 1.404(4) . ? N9 C31 1.326(4) . ? N9 C27 1.342(4) . ? N10 C32 1.365(4) . ? N10 C31 1.395(4) . ? C2 C3 1.509(5) . ? C3 C4 1.383(5) . ? C4 C5 1.388(5) . ? C5 C6 1.370(5) . ? C6 C7 1.413(5) . ? C8 C9 1.511(5) . ? C9 C10 1.402(5) . ? C10 C11 1.372(5) . ? C11 C12 1.385(5) . ? C12 C13 1.402(5) . ? C14 C15 1.512(5) . ? C15 C16 1.385(5) . ? C16 C17 1.390(5) . ? C17 C18 1.375(5) . ? C18 C19 1.404(4) . ? C20 C21 1.507(5) . ? C21 C22 1.392(5) . ? C22 C23 1.383(5) . ? C23 C24 1.379(5) . ? C24 C25 1.405(4) . ? C26 C27 1.509(4) . ? C27 C28 1.391(4) . ? C28 C29 1.397(5) . ? C29 C30 1.372(5) . ? C30 C31 1.402(4) . ? C33 C34 1.504(4) . ? C34 C35 1.392(5) . ? C34 C39 1.394(5) . ? C35 C36 1.389(5) . ? C36 C37 1.386(5) . ? C37 C38 1.379(5) . ? C38 C39 1.393(5) . ? 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 Cl1 C1S Cl2 105.0(7) . . ? Cl3 C2S Cl4 109.7(7) . . ? C2 O1 C1 113.8(3) . . ? C32 O8 C33 117.4(2) . . ? C7 N1 C3 117.9(3) . . ? C8 N2 C7 127.2(3) . . ? C9 N3 C13 117.7(3) . . ? C14 N4 C13 129.5(3) . . ? C19 N5 C15 118.4(3) . . ? C20 N6 C19 128.6(3) . . ? C25 N7 C21 117.9(3) . . ? C26 N8 C25 128.8(3) . . ? C31 N9 C27 118.3(3) . . ? C32 N10 C31 128.6(3) . . ? O2 C2 O1 124.3(3) . . ? O2 C2 C3 124.0(3) . . ? O1 C2 C3 111.7(3) . . ? N1 C3 C4 123.6(3) . . ? N1 C3 C2 114.2(3) . . ? C4 C3 C2 122.2(3) . . ? C3 C4 C5 117.7(3) . . ? C6 C5 C4 120.2(3) . . ? C5 C6 C7 118.2(3) . . ? N1 C7 N2 114.1(3) . . ? N1 C7 C6 122.4(3) . . ? N2 C7 C6 123.5(3) . . ? O3 C8 N2 124.5(3) . . ? O3 C8 C9 121.3(3) . . ? N2 C8 C9 114.3(3) . . ? N3 C9 C10 124.2(3) . . ? N3 C9 C8 118.0(3) . . ? C10 C9 C8 117.8(3) . . ? C11 C10 C9 116.8(3) . . ? C10 C11 C12 120.9(3) . . ? C11 C12 C13 117.4(3) . . ? N3 C13 N4 114.0(3) . . ? N3 C13 C12 123.1(3) . . ? N4 C13 C12 122.9(3) . . ? O4 C14 N4 125.6(3) . . ? O4 C14 C15 121.5(3) . . ? N4 C14 C15 112.9(3) . . ? N5 C15 C16 123.1(3) . . ? N5 C15 C14 117.1(3) . . ? C16 C15 C14 119.7(3) . . ? C15 C16 C17 117.6(3) . . ? C18 C17 C16 120.5(3) . . ? C17 C18 C19 117.6(3) . . ? N5 C19 N6 113.3(3) . . ? N5 C19 C18 122.6(3) . . ? N6 C19 C18 124.1(3) . . ? O5 C20 N6 125.1(3) . . ? O5 C20 C21 122.2(3) . . ? N6 C20 C21 112.7(3) . . ? N7 C21 C22 123.5(3) . . ? N7 C21 C20 116.6(3) . . ? C22 C21 C20 119.9(3) . . ? C23 C22 C21 117.1(3) . . ? C24 C23 C22 120.8(3) . . ? C23 C24 C25 117.3(3) . . ? N7 C25 N8 113.0(3) . . ? N7 C25 C24 123.3(3) . . ? N8 C25 C24 123.7(3) . . ? O6 C26 N8 125.0(3) . . ? O6 C26 C27 122.4(3) . . ? N8 C26 C27 112.6(3) . . ? N9 C27 C28 123.2(3) . . ? N9 C27 C26 117.0(3) . . ? C28 C27 C26 119.8(3) . . ? C27 C28 C29 117.0(3) . . ? C30 C29 C28 120.8(3) . . ? C29 C30 C31 117.3(3) . . ? N9 C31 N10 113.3(3) . . ? N9 C31 C30 123.4(3) . . ? N10 C31 C30 123.3(3) . . ? O7 C32 O8 125.2(3) . . ? O7 C32 N10 127.2(3) . . ? O8 C32 N10 107.6(3) . . ? O8 C33 C34 107.3(3) . . ? C35 C34 C39 119.2(3) . . ? C35 C34 C33 118.8(3) . . ? C39 C34 C33 122.0(3) . . ? C36 C35 C34 120.4(3) . . ? C37 C36 C35 120.1(3) . . ? C38 C37 C36 120.0(3) . . ? C37 C38 C39 120.2(3) . . ? C38 C39 C34 120.1(3) . . ? 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 N10 H10N Cl4 0.87(2) 2.65(3) 3.395(5) 143(3) 4_565 N10 H10N Cl1 0.87(2) 2.61(2) 3.483(5) 174(4) 4_565 N8 H8N Cl2 0.889(19) 2.85(3) 3.584(4) 141(3) . N8 H8N Cl4 0.889(19) 2.93(2) 3.770(5) 158(3) 4_565 N6 H6N Cl3 0.88(2) 3.00(3) 3.677(5) 135(3) . N6 H6N Cl4 0.88(2) 2.75(2) 3.601(5) 161(3) 4_565 N6 H6N Cl2 0.88(2) 2.79(2) 3.642(5) 162(3) . N4 H4N Cl4 0.88(2) 2.86(3) 3.503(6) 132(3) 4_565 N4 H4N Cl2 0.88(2) 2.82(3) 3.554(4) 142(3) . N4 H4N N5 0.88(2) 2.08(4) 2.654(4) 122(3) . N2 H2N Cl2 0.88(2) 2.81(3) 3.585(6) 148(4) . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.555 _refine_diff_density_min -0.866 _refine_diff_density_rms 0.088