# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Dr. Patrick Batail' _publ_contact_author_email patrick.batail@univ-angers.fr loop_ _publ_author_name C.Lemouchi S.Simonov L.Zorina C.Gautier P.Hudhomme P.Batail data_PDI-Cl4-[Gly-Ala(OEt)]2-150K _database_code_depnum_ccdc_archive 'CCDC 833909' #TrackingRef 'cl160-150K.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_compound_source 'synthesis as described' _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C38 H28 Cl4 N4 O10' _chemical_formula_sum 'C38 H28 Cl4 N4 O10' _chemical_formula_weight 842.44 _chemical_absolute_configuration rm 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' 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 triclinic _symmetry_space_group_name_H-M 'P 1' _symmetry_space_group_name_Hall 'P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 9.978(3) _cell_length_b 10.704(3) _cell_length_c 17.817(6) _cell_angle_alpha 74.10(2) _cell_angle_beta 81.31(2) _cell_angle_gamma 81.28(2) _cell_volume 1796.9(9) _cell_formula_units_Z 2 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2 _cell_measurement_theta_max 28 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.015 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.557 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 0.397 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.75 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Nonius KappaCCD' _diffrn_measurement_method 'combined \f and \w-scans' _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_detector_area_resol_mean 9 _diffrn_standards_decay_% ? _diffrn_reflns_number 16721 _diffrn_reflns_av_R_equivalents 0.0668 _diffrn_reflns_av_sigmaI/netI 0.1399 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 28.00 _reflns_number_total 11506 _reflns_number_gt 6817 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND 3.1 (Crystal Impact GbR 2005)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^ > 2\s(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^)+(0.0428P)^2^+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.05(8) _refine_ls_number_reflns 11506 _refine_ls_number_parameters 885 _refine_ls_number_restraints 19 _refine_ls_R_factor_all 0.1485 _refine_ls_R_factor_gt 0.0713 _refine_ls_wR_factor_ref 0.1354 _refine_ls_wR_factor_gt 0.1169 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.014 _refine_ls_shift/su_max 0.004 _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 0.9777(3) 0.9286(2) 0.37537(13) 0.0339(7) Uani 1 1 d . . . Cl2 Cl 0.8961(2) 0.6243(2) 0.02979(13) 0.0229(6) Uani 1 1 d . . . C1 C 0.9227(10) 0.8415(8) 0.2534(5) 0.0169(8) Uani 1 1 d . . . C2 C 0.9437(10) 0.7161(8) 0.1513(5) 0.0177(8) Uani 1 1 d . . . C3 C 0.9048(10) 0.8322(8) 0.3327(5) 0.0197(9) Uani 1 1 d . . . C4 C 0.8935(10) 0.7323(8) 0.2297(5) 0.0176(8) Uani 1 1 d . . . C5 C 0.8813(10) 0.6239(8) 0.1283(5) 0.0190(9) Uani 1 1 d . . . C6 C 0.8332(10) 0.7354(9) 0.3859(6) 0.025(2) Uani 1 1 d . . . H6 H 0.8219 0.7330 0.4391 0.030 Uiso 1 1 calc R . . C7 C 0.8128(10) 0.6423(8) 0.2808(5) 0.0183(8) Uani 1 1 d . . . C8 C 0.7968(10) 0.5432(8) 0.1784(5) 0.0197(9) Uani 1 1 d . . . H8 H 0.7606 0.4834 0.1602 0.024 Uiso 1 1 calc R . . C9 C 0.7787(11) 0.6430(9) 0.3616(5) 0.0221(10) Uani 1 1 d . . . C10 C 0.7627(10) 0.5470(8) 0.2556(5) 0.0180(8) Uani 1 1 d . . . C11 C 0.7043(11) 0.5455(9) 0.4178(6) 0.027(2) Uani 1 1 d . . . C12 C 0.6701(11) 0.4587(9) 0.3075(6) 0.0226(9) Uani 1 1 d . . . N1 N 0.6455(9) 0.4639(7) 0.3855(5) 0.026(2) Uani 1 1 d . . . O1 O 0.6848(7) 0.5377(6) 0.4876(4) 0.0389(19) Uani 1 1 d . . . O2 O 0.6130(7) 0.3833(6) 0.2856(4) 0.0289(18) Uani 1 1 d . . . C13 C 0.5537(12) 0.3705(9) 0.4375(6) 0.038(3) Uani 1 1 d . . . H13A H 0.4658 0.3853 0.4176 0.046 Uiso 1 1 calc R . . H13B H 0.5394 0.3834 0.4901 0.046 Uiso 1 1 calc R . . C14 C 0.6192(13) 0.2319(10) 0.4397(6) 0.030(3) Uani 1 1 d . . . O3 O 0.7426(9) 0.1966(7) 0.4354(4) 0.040(2) Uani 1 1 d . . . N2 N 0.5257(10) 0.1465(8) 0.4513(5) 0.044(3) Uani 1 1 d . . . H2 H 0.4403 0.1740 0.4574 0.052 Uiso 1 1 calc R . . C15 C 0.5672(12) 0.0097(9) 0.4535(6) 0.0353(12) Uani 1 1 d . A . H15 H 0.6429 0.0057 0.4119 0.042 Uiso 1 1 calc R . . C16 C 0.6157(14) -0.0691(10) 0.5292(6) 0.048(2) Uani 1 1 d . . . H16A H 0.5486 -0.0561 0.5719 0.072 Uiso 1 1 calc R . . H16B H 0.7001 -0.0418 0.5349 0.072 Uiso 1 1 calc R . . H16C H 0.6296 -0.1600 0.5297 0.072 Uiso 1 1 calc R . . C17 C 0.4531(14) -0.0502(10) 0.4362(8) 0.053(3) Uani 1 1 d D . . O4A O 0.3357(16) 0.011(2) 0.4219(10) 0.077(4) Uani 0.60 1 d PDU A 1 O5A O 0.491(2) -0.1687(11) 0.4316(15) 0.064(6) Uani 0.60 1 d PD A 1 C18A C 0.390(3) -0.245(2) 0.4169(11) 0.082(5) Uani 0.60 1 d PD A 1 H18A H 0.3261 -0.1878 0.3827 0.099 Uiso 0.60 1 calc PR A 1 H18B H 0.4353 -0.3120 0.3917 0.099 Uiso 0.60 1 calc PR A 1 C19A C 0.319(2) -0.303(2) 0.4903(11) 0.082(5) Uani 0.60 1 d PD A 1 H19A H 0.2489 -0.3483 0.4824 0.123 Uiso 0.60 1 calc PR A 1 H19B H 0.2787 -0.2358 0.5161 0.123 Uiso 0.60 1 calc PR A 1 H19C H 0.3820 -0.3631 0.5224 0.123 Uiso 0.60 1 calc PR A 1 O4B O 0.360(2) 0.024(3) 0.3959(16) 0.077(4) Uani 0.40 1 d PDU A 2 O5B O 0.448(4) -0.1729(16) 0.452(2) 0.064(6) Uani 0.40 1 d PD A 2 C18B C 0.325(4) -0.224(3) 0.441(2) 0.082(5) Uani 0.40 1 d PD A 2 H18C H 0.2529 -0.2175 0.4830 0.099 Uiso 0.40 1 calc PR A 2 H18D H 0.2919 -0.1743 0.3914 0.099 Uiso 0.40 1 calc PR A 2 C19B C 0.362(3) -0.357(2) 0.4396(18) 0.082(5) Uani 0.40 1 d PD A 2 H19D H 0.2811 -0.3957 0.4387 0.123 Uiso 0.40 1 calc PR A 2 H19E H 0.4042 -0.4036 0.4858 0.123 Uiso 0.40 1 calc PR A 2 H19F H 0.4240 -0.3621 0.3937 0.123 Uiso 0.40 1 calc PR A 2 Cl3 Cl 1.1901(2) 0.59985(19) 0.04318(13) 0.0219(6) Uani 1 1 d . . . Cl4 Cl 0.8279(3) 1.1463(2) 0.25210(15) 0.0327(7) Uani 1 1 d . . . C20 C 1.0480(10) 0.7946(8) 0.1067(5) 0.0167(8) Uani 1 1 d . . . C21 C 0.9718(10) 0.9517(8) 0.1910(5) 0.0179(9) Uani 1 1 d . . . C22 C 1.1524(10) 0.7582(8) 0.0513(5) 0.0181(9) Uani 1 1 d . . . C23 C 1.0522(10) 0.9204(8) 0.1207(5) 0.0155(8) Uani 1 1 d . . . C24 C 0.9542(10) 1.0837(8) 0.1911(5) 0.0218(9) Uani 1 1 d . . . C25 C 1.2383(10) 0.8465(8) 0.0026(5) 0.018(2) Uani 1 1 d . . . H25 H 1.3020 0.8212 -0.0359 0.021 Uiso 1 1 calc R . . C26 C 1.1361(11) 1.0100(8) 0.0728(5) 0.0180(8) Uani 1 1 d . . . C27 C 1.0307(10) 1.1752(9) 0.1370(5) 0.0230(9) Uani 1 1 d . . . H27 H 1.0164 1.2623 0.1386 0.028 Uiso 1 1 calc R . . C28 C 1.2279(10) 0.9726(8) 0.0119(5) 0.0184(9) Uani 1 1 d . . . C29 C 1.1280(10) 1.1362(8) 0.0808(5) 0.0199(9) Uani 1 1 d . . . C30 C 1.3251(11) 1.0612(8) -0.0363(6) 0.022(2) Uani 1 1 d . . . C31 C 1.2178(11) 1.2290(9) 0.0326(5) 0.0244(9) Uani 1 1 d . . . N3 N 1.3201(9) 1.1820(7) -0.0212(4) 0.0230(9) Uani 1 1 d . . . O6 O 1.4090(7) 1.0319(6) -0.0877(4) 0.0306(19) Uani 1 1 d . . . O7 O 1.2130(8) 1.3392(6) 0.0370(4) 0.041(2) Uani 1 1 d . . . C32 C 1.4134(11) 1.2709(8) -0.0693(5) 0.022(2) Uani 1 1 d . . . H32A H 1.5034 1.2228 -0.0748 0.026 Uiso 1 1 calc R . . H32B H 1.4198 1.3372 -0.0426 0.026 Uiso 1 1 calc R . . C33 C 1.3729(9) 1.3359(8) -0.1482(5) 0.022(2) Uani 1 1 d . . . O8 O 1.2562(7) 1.3330(5) -0.1640(3) 0.0350(15) Uani 1 1 d . . . N4 N 1.4687(8) 1.4000(6) -0.2000(4) 0.0345(18) Uani 1 1 d . . . H4 H 1.5444 1.4063 -0.1846 0.041 Uiso 1 1 calc R . . C34 C 1.4459(10) 1.4581(8) -0.2810(5) 0.040(2) Uani 1 1 d . . . H34 H 1.3618 1.5188 -0.2814 0.048 Uiso 1 1 calc R . . C35 C 1.5609(11) 1.5368(9) -0.3220(5) 0.058(3) Uani 1 1 d . . . H35A H 1.5590 1.6092 -0.2997 0.086 Uiso 1 1 calc R . . H35B H 1.5507 1.5689 -0.3770 0.086 Uiso 1 1 calc R . . H35C H 1.6464 1.4824 -0.3156 0.086 Uiso 1 1 calc R . . C36 C 1.4273(11) 1.3592(10) -0.3241(5) 0.042(2) Uani 1 1 d . . . O9 O 1.3759(8) 1.3862(6) -0.3836(4) 0.068(2) Uani 1 1 d . . . O10 O 1.4883(7) 1.2415(6) -0.2934(3) 0.0489(16) Uani 1 1 d . . . C37 C 1.4750(11) 1.1367(8) -0.3285(5) 0.054(3) Uani 1 1 d . . . H37A H 1.5205 1.1531 -0.3818 0.065 Uiso 1 1 calc R . . H37B H 1.3795 1.1303 -0.3299 0.065 Uiso 1 1 calc R . . C38 C 1.5403(13) 1.0126(9) -0.2781(6) 0.060(4) Uani 1 1 d . . . H38A H 1.6343 1.0208 -0.2767 0.090 Uiso 1 1 calc R . . H38B H 1.5347 0.9408 -0.2996 0.090 Uiso 1 1 calc R . . H38C H 1.4935 0.9971 -0.2258 0.090 Uiso 1 1 calc R . . Cl5 Cl 0.5167(2) 0.6180(2) -0.10183(12) 0.0241(6) Uani 1 1 d . . . Cl6 Cl 0.5872(3) 0.9144(2) 0.24815(12) 0.0236(6) Uani 1 1 d . . . C41 C 0.5677(10) 0.7021(8) 0.0223(5) 0.0169(8) Uani 1 1 d . . . C42 C 0.5465(10) 0.8278(8) 0.1223(5) 0.0177(8) Uani 1 1 d . . . C43 C 0.5933(10) 0.7131(8) -0.0598(5) 0.0197(9) Uani 1 1 d . . . C44 C 0.5998(10) 0.8110(8) 0.0474(5) 0.0176(8) Uani 1 1 d . . . C45 C 0.6045(10) 0.9136(8) 0.1505(5) 0.0190(9) Uani 1 1 d . . . C46 C 0.6713(9) 0.8030(7) -0.1102(5) 0.016(2) Uani 1 1 d . . . H46 H 0.6916 0.8027 -0.1629 0.019 Uiso 1 1 calc R . . C47 C 0.6809(10) 0.9019(8) -0.0056(5) 0.0183(8) Uani 1 1 d . . . C48 C 0.6935(10) 0.9994(8) 0.1008(5) 0.0197(9) Uani 1 1 d . . . H48 H 0.7297 1.0578 0.1201 0.024 Uiso 1 1 calc R . . C49 C 0.7186(11) 0.8924(9) -0.0828(5) 0.0221(10) Uani 1 1 d . . . C50 C 0.7263(10) 0.9965(8) 0.0240(5) 0.0180(8) Uani 1 1 d . . . C51 C 0.8136(10) 0.9817(8) -0.1361(5) 0.019(2) Uani 1 1 d . . . C52 C 0.8234(11) 1.0853(9) -0.0274(5) 0.0226(9) Uani 1 1 d . . . N11 N 0.8602(9) 1.0743(7) -0.1050(4) 0.0211(19) Uani 1 1 d . . . O11 O 0.8519(7) 0.9777(6) -0.2032(3) 0.041(2) Uani 1 1 d . . . O12 O 0.8694(7) 1.1645(5) -0.0052(3) 0.0235(17) Uani 1 1 d . . . C53 C 0.9455(10) 1.1677(7) -0.1543(5) 0.020(2) Uani 1 1 d . . . H53A H 0.9673 1.1496 -0.2054 0.024 Uiso 1 1 calc R . . H53B H 1.0304 1.1576 -0.1318 0.024 Uiso 1 1 calc R . . C54 C 0.8804(12) 1.3074(10) -0.1645(5) 0.024(2) Uani 1 1 d . . . O13 O 0.7553(8) 1.3303(6) -0.1644(4) 0.0331(18) Uani 1 1 d . . . N12 N 0.9605(9) 1.3950(7) -0.1714(4) 0.024(2) Uani 1 1 d . . . H12 H 1.0467 1.3713 -0.1708 0.028 Uiso 1 1 calc R . . C55 C 0.9096(13) 1.5337(9) -0.1801(6) 0.0353(12) Uani 1 1 d . . . H55 H 0.8263 1.5395 -0.1436 0.042 Uiso 1 1 calc R . . C56 C 1.0173(13) 1.5998(10) -0.1567(6) 0.048(2) Uani 1 1 d . . . H56A H 1.0395 1.5528 -0.1051 0.072 Uiso 1 1 calc R . . H56B H 0.9818 1.6883 -0.1568 0.072 Uiso 1 1 calc R . . H56C H 1.0980 1.5995 -0.1937 0.072 Uiso 1 1 calc R . . C57 C 0.8762(13) 1.6070(9) -0.2639(6) 0.041(3) Uani 1 1 d . . . O14 O 0.7989(6) 1.7039(5) -0.2747(3) 0.0450(16) Uani 1 1 d . . . O15 O 0.9496(6) 1.5520(5) -0.3166(3) 0.0415(15) Uani 1 1 d . . . C58 C 0.9381(11) 1.6232(8) -0.3979(4) 0.053(3) Uani 1 1 d . . . H58A H 0.9778 1.7047 -0.4104 0.063 Uiso 1 1 calc R . . H58B H 0.8431 1.6425 -0.4076 0.063 Uiso 1 1 calc R . . C59 C 1.0140(14) 1.5357(12) -0.4456(6) 0.085(5) Uani 1 1 d . . . H59A H 1.1040 1.5079 -0.4300 0.128 Uiso 1 1 calc R . . H59B H 1.0205 1.5819 -0.5002 0.128 Uiso 1 1 calc R . . H59C H 0.9667 1.4606 -0.4376 0.128 Uiso 1 1 calc R . . Cl7 Cl 0.2936(2) 0.94496(19) 0.22757(13) 0.0214(6) Uani 1 1 d . . . Cl8 Cl 0.6632(3) 0.3997(2) 0.02168(13) 0.0250(6) Uani 1 1 d . . . C60 C 0.4360(10) 0.7502(8) 0.1661(5) 0.0167(8) Uani 1 1 d . . . C61 C 0.5118(10) 0.5969(8) 0.0836(5) 0.0179(9) Uani 1 1 d . . . C62 C 0.3318(10) 0.7851(8) 0.2203(5) 0.0181(9) Uani 1 1 d . . . C63 C 0.4345(10) 0.6273(8) 0.1496(5) 0.0155(8) Uani 1 1 d . . . C64 C 0.5352(11) 0.4634(8) 0.0826(5) 0.0218(9) Uani 1 1 d . . . C65 C 0.2468(10) 0.6970(8) 0.2661(5) 0.020(2) Uani 1 1 d . . . H65 H 0.1796 0.7239 0.3025 0.024 Uiso 1 1 calc R . . C66 C 0.3539(11) 0.5364(8) 0.2020(5) 0.0180(8) Uani 1 1 d . . . C67 C 0.4591(10) 0.3708(9) 0.1351(5) 0.0230(9) Uani 1 1 d . . . H67 H 0.4724 0.2847 0.1315 0.028 Uiso 1 1 calc R . . C68 C 0.2571(10) 0.5734(8) 0.2603(5) 0.0184(9) Uani 1 1 d . . . C69 C 0.3645(10) 0.4064(8) 0.1920(5) 0.0199(9) Uani 1 1 d . . . C70 C 0.1670(11) 0.4787(9) 0.3119(5) 0.022(2) Uani 1 1 d . . . C71 C 0.2753(11) 0.3110(9) 0.2437(6) 0.0244(9) Uani 1 1 d . . . N13 N 0.1838(9) 0.3540(7) 0.3013(4) 0.0230(9) Uani 1 1 d . . . O16 O 0.0779(7) 0.5100(6) 0.3605(4) 0.032(2) Uani 1 1 d . . . O17 O 0.2779(8) 0.2017(6) 0.2348(4) 0.040(2) Uani 1 1 d . . . C72 C 0.0945(12) 0.2633(9) 0.3539(6) 0.033(3) Uani 1 1 d . . . H72A H 0.1114 0.1802 0.3402 0.039 Uiso 1 1 calc R . . H72B H 0.0000 0.2979 0.3478 0.039 Uiso 1 1 calc R . . C73 C 0.1197(11) 0.2424(7) 0.4401(5) 0.025(2) Uani 1 1 d . . . O18 O 0.2265(7) 0.2540(6) 0.4594(3) 0.0425(17) Uani 1 1 d . . . N14 N 0.0088(8) 0.2072(6) 0.4900(4) 0.0362(18) Uani 1 1 d . . . H14 H -0.0652 0.2042 0.4716 0.043 Uiso 1 1 calc R . . C74 C 0.0115(10) 0.1738(10) 0.5748(5) 0.045(3) Uani 1 1 d . . . H74 H 0.0639 0.2338 0.5879 0.053 Uiso 1 1 calc R . . C75 C -0.1356(10) 0.1899(10) 0.6131(5) 0.066(3) Uani 1 1 d . . . H75A H -0.1796 0.2743 0.5885 0.098 Uiso 1 1 calc R . . H75B H -0.1359 0.1824 0.6680 0.098 Uiso 1 1 calc R . . H75C H -0.1838 0.1230 0.6067 0.098 Uiso 1 1 calc R . . C76 C 0.0775(11) 0.0351(8) 0.6029(6) 0.046(3) Uani 1 1 d . . . O19 O 0.0821(8) -0.0480(6) 0.5715(4) 0.074(2) Uani 1 1 d . . . O20 O 0.1257(6) 0.0203(5) 0.6719(3) 0.0460(16) Uani 1 1 d . . . C77 C 0.1818(11) -0.1115(8) 0.7100(5) 0.057(3) Uani 1 1 d . . . H77A H 0.2660 -0.1366 0.6799 0.068 Uiso 1 1 calc R . . H77B H 0.1177 -0.1728 0.7130 0.068 Uiso 1 1 calc R . . C78 C 0.2083(11) -0.1143(10) 0.7896(6) 0.059(3) Uani 1 1 d . . . H78A H 0.2520 -0.0393 0.7874 0.089 Uiso 1 1 calc R . . H78B H 0.2666 -0.1925 0.8100 0.089 Uiso 1 1 calc R . . H78C H 0.1235 -0.1130 0.8231 0.089 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 0.040(2) 0.0419(15) 0.0283(14) -0.0206(13) -0.0028(14) -0.0121(14) Cl2 0.0219(16) 0.0275(13) 0.0225(13) -0.0095(11) -0.0059(11) -0.0037(11) C1 0.014(2) 0.0145(18) 0.0222(19) -0.0056(16) -0.0022(16) -0.0013(16) C2 0.019(2) 0.0143(18) 0.0206(19) -0.0067(16) -0.0024(17) 0.0013(16) C3 0.020(2) 0.0169(19) 0.024(2) -0.0113(17) -0.0003(18) -0.0010(17) C4 0.018(2) 0.0148(18) 0.0197(19) -0.0034(16) -0.0058(17) 0.0012(16) C5 0.023(2) 0.0173(19) 0.0181(19) -0.0072(17) -0.0016(17) -0.0019(17) C6 0.020(6) 0.037(6) 0.024(5) -0.018(5) -0.010(5) 0.006(5) C7 0.019(2) 0.0143(18) 0.0191(19) -0.0022(16) -0.0046(17) 0.0032(16) C8 0.020(2) 0.0157(19) 0.027(2) -0.0086(18) -0.0094(18) -0.0001(16) C9 0.024(3) 0.019(2) 0.021(2) -0.0028(18) 0.0021(18) -0.0039(18) C10 0.016(2) 0.0148(18) 0.021(2) -0.0001(17) -0.0032(17) -0.0013(16) C11 0.024(6) 0.019(5) 0.030(6) 0.006(4) -0.002(4) -0.001(4) C12 0.022(2) 0.019(2) 0.026(2) -0.0043(18) -0.0074(19) 0.0025(18) N1 0.024(5) 0.023(4) 0.030(5) -0.005(4) -0.002(4) -0.007(4) O1 0.052(5) 0.046(4) 0.019(3) -0.005(3) 0.005(3) -0.022(3) O2 0.034(5) 0.021(4) 0.032(4) -0.008(3) 0.002(3) -0.004(3) C13 0.049(8) 0.045(7) 0.021(5) -0.014(5) 0.015(5) -0.016(6) C14 0.039(9) 0.027(6) 0.025(6) -0.010(5) -0.003(6) -0.003(6) O3 0.031(5) 0.045(4) 0.040(4) -0.002(4) -0.007(4) -0.002(4) N2 0.036(7) 0.034(5) 0.053(6) -0.006(5) 0.019(5) -0.012(5) C15 0.039(3) 0.026(2) 0.040(3) -0.012(2) 0.005(2) -0.003(2) C16 0.069(7) 0.045(5) 0.030(4) -0.009(4) -0.003(4) -0.011(5) C17 0.048(8) 0.027(6) 0.085(8) -0.022(6) -0.002(7) 0.003(5) O4A 0.074(7) 0.073(5) 0.095(8) -0.033(6) -0.016(6) -0.020(5) O5A 0.093(15) 0.040(4) 0.057(15) -0.003(5) -0.009(11) -0.023(5) C18A 0.092(14) 0.088(9) 0.067(10) 0.010(7) -0.031(9) -0.045(9) C19A 0.092(14) 0.088(9) 0.067(10) 0.010(7) -0.031(9) -0.045(9) O4B 0.074(7) 0.073(5) 0.095(8) -0.033(6) -0.016(6) -0.020(5) O5B 0.093(15) 0.040(4) 0.057(15) -0.003(5) -0.009(11) -0.023(5) C18B 0.092(14) 0.088(9) 0.067(10) 0.010(7) -0.031(9) -0.045(9) C19B 0.092(14) 0.088(9) 0.067(10) 0.010(7) -0.031(9) -0.045(9) Cl3 0.0267(17) 0.0153(12) 0.0251(13) -0.0093(11) -0.0046(12) 0.0025(11) Cl4 0.0286(18) 0.0291(14) 0.0446(16) -0.0206(14) 0.0032(14) -0.0033(12) C20 0.018(2) 0.0166(18) 0.0155(18) -0.0023(16) -0.0065(16) -0.0001(16) C21 0.018(2) 0.018(2) 0.021(2) -0.0095(17) -0.0058(17) -0.0034(17) C22 0.018(2) 0.0130(18) 0.025(2) -0.0058(17) -0.0064(18) -0.0042(16) C23 0.019(2) 0.0137(18) 0.0158(19) -0.0053(16) -0.0062(17) -0.0021(16) C24 0.023(2) 0.024(2) 0.020(2) -0.0095(18) -0.0040(18) -0.0013(18) C25 0.017(6) 0.024(5) 0.009(4) 0.003(4) 0.002(4) -0.011(4) C26 0.019(2) 0.0167(18) 0.0205(19) -0.0066(16) -0.0088(17) 0.0016(16) C27 0.024(2) 0.0176(19) 0.031(2) -0.0100(19) -0.0101(19) 0.0018(17) C28 0.019(2) 0.0173(19) 0.0195(19) -0.0050(17) -0.0061(17) 0.0007(16) C29 0.024(2) 0.0161(19) 0.0216(19) -0.0053(17) -0.0028(18) -0.0062(17) C30 0.022(7) 0.017(5) 0.028(6) -0.005(5) -0.003(5) -0.006(5) C31 0.028(3) 0.021(2) 0.026(2) -0.0079(18) -0.0046(19) -0.0031(18) N3 0.027(2) 0.0177(17) 0.0250(19) -0.0039(15) -0.0019(17) -0.0088(16) O6 0.025(5) 0.026(4) 0.039(4) -0.009(4) 0.007(4) -0.007(3) O7 0.064(7) 0.011(4) 0.043(5) -0.009(3) 0.014(4) -0.007(4) C32 0.027(6) 0.026(5) 0.016(4) -0.008(4) 0.000(4) -0.011(4) C33 0.017(5) 0.026(5) 0.025(5) -0.011(4) -0.008(4) 0.004(4) O8 0.020(4) 0.048(4) 0.028(3) 0.003(3) -0.006(3) 0.003(3) N4 0.036(5) 0.044(4) 0.024(4) -0.001(3) -0.004(3) -0.019(4) C34 0.056(7) 0.028(5) 0.029(5) 0.004(4) 0.006(5) -0.015(5) C35 0.071(8) 0.070(6) 0.029(5) 0.001(5) 0.002(5) -0.034(6) C36 0.038(7) 0.052(6) 0.030(5) 0.000(5) -0.002(5) -0.011(5) O9 0.087(6) 0.073(5) 0.048(4) -0.002(4) -0.038(4) -0.012(4) O10 0.067(5) 0.046(4) 0.038(3) -0.014(3) -0.015(3) -0.005(3) C37 0.078(8) 0.050(6) 0.039(5) -0.014(5) -0.012(5) -0.011(5) C38 0.083(10) 0.047(6) 0.046(6) -0.009(5) -0.012(6) 0.001(6) Cl5 0.0246(17) 0.0288(13) 0.0245(13) -0.0132(12) -0.0019(12) -0.0095(12) Cl6 0.0303(17) 0.0252(13) 0.0190(13) -0.0116(11) -0.0006(12) -0.0061(11) C41 0.014(2) 0.0145(18) 0.0222(19) -0.0056(16) -0.0022(16) -0.0013(16) C42 0.019(2) 0.0143(18) 0.0206(19) -0.0067(16) -0.0024(17) 0.0013(16) C43 0.020(2) 0.0169(19) 0.024(2) -0.0113(17) -0.0003(18) -0.0010(17) C44 0.018(2) 0.0148(18) 0.0197(19) -0.0034(16) -0.0058(17) 0.0012(16) C45 0.023(2) 0.0173(19) 0.0181(19) -0.0072(17) -0.0016(17) -0.0019(17) C46 0.015(5) 0.012(4) 0.015(5) 0.002(4) 0.003(4) 0.004(4) C47 0.019(2) 0.0143(18) 0.0191(19) -0.0022(16) -0.0046(17) 0.0032(16) C48 0.020(2) 0.0157(19) 0.027(2) -0.0086(18) -0.0094(18) -0.0001(16) C49 0.024(3) 0.019(2) 0.021(2) -0.0028(18) 0.0021(18) -0.0039(18) C50 0.016(2) 0.0148(18) 0.021(2) -0.0001(17) -0.0032(17) -0.0013(16) C51 0.018(5) 0.018(4) 0.020(5) -0.007(4) -0.001(4) -0.001(4) C52 0.022(2) 0.019(2) 0.026(2) -0.0043(18) -0.0074(19) 0.0025(18) N11 0.027(5) 0.018(4) 0.017(4) -0.006(3) 0.006(4) -0.008(3) O11 0.063(5) 0.039(4) 0.024(3) -0.015(3) 0.012(3) -0.020(3) O12 0.025(4) 0.023(3) 0.024(4) 0.000(3) -0.006(3) -0.015(3) C53 0.016(6) 0.012(4) 0.030(5) 0.001(4) -0.004(4) -0.006(4) C54 0.020(7) 0.035(6) 0.013(5) 0.002(5) 0.001(5) -0.009(5) O13 0.026(5) 0.025(3) 0.044(4) 0.001(3) -0.006(4) -0.003(3) N12 0.020(6) 0.021(4) 0.028(4) -0.002(4) -0.005(4) -0.003(4) C55 0.039(3) 0.026(2) 0.040(3) -0.012(2) 0.005(2) -0.003(2) C56 0.069(7) 0.045(5) 0.030(4) -0.009(4) -0.003(4) -0.011(5) C57 0.065(8) 0.021(5) 0.038(6) -0.014(5) -0.003(6) -0.001(5) O14 0.051(4) 0.026(3) 0.055(4) -0.015(3) -0.015(3) 0.020(3) O15 0.056(4) 0.038(3) 0.025(3) -0.007(3) -0.003(3) 0.007(3) C58 0.070(8) 0.050(5) 0.033(5) -0.008(5) -0.005(5) 0.004(5) C59 0.097(12) 0.121(11) 0.035(6) -0.037(7) -0.009(7) 0.032(9) Cl7 0.0210(16) 0.0172(12) 0.0286(13) -0.0112(11) -0.0011(12) -0.0026(10) Cl8 0.0244(17) 0.0204(13) 0.0326(14) -0.0155(12) 0.0041(12) -0.0012(11) C60 0.018(2) 0.0166(18) 0.0155(18) -0.0023(16) -0.0065(16) -0.0001(16) C61 0.018(2) 0.018(2) 0.021(2) -0.0095(17) -0.0058(17) -0.0034(17) C62 0.018(2) 0.0130(18) 0.025(2) -0.0058(17) -0.0064(18) -0.0042(16) C63 0.019(2) 0.0137(18) 0.0158(19) -0.0053(16) -0.0062(17) -0.0021(16) C64 0.023(2) 0.024(2) 0.020(2) -0.0095(18) -0.0040(18) -0.0013(18) C65 0.023(7) 0.019(5) 0.021(5) -0.015(4) -0.005(4) 0.009(4) C66 0.019(2) 0.0167(18) 0.0205(19) -0.0066(16) -0.0088(17) 0.0016(16) C67 0.024(2) 0.0176(19) 0.031(2) -0.0100(19) -0.0101(19) 0.0018(17) C68 0.019(2) 0.0173(19) 0.0195(19) -0.0050(17) -0.0061(17) 0.0007(16) C69 0.024(2) 0.0161(19) 0.0216(19) -0.0053(17) -0.0028(18) -0.0062(17) C70 0.020(7) 0.027(6) 0.017(5) -0.001(5) -0.006(5) 0.000(5) C71 0.028(3) 0.021(2) 0.026(2) -0.0079(18) -0.0046(19) -0.0031(18) N13 0.027(2) 0.0177(17) 0.0250(19) -0.0039(15) -0.0019(17) -0.0088(16) O16 0.034(6) 0.030(4) 0.028(4) -0.006(4) 0.006(4) -0.006(4) O17 0.053(6) 0.023(4) 0.048(5) -0.019(4) 0.009(4) -0.015(4) C72 0.038(7) 0.020(5) 0.038(6) -0.004(5) 0.004(5) -0.011(5) C73 0.044(7) 0.013(4) 0.015(4) -0.001(3) -0.006(4) 0.001(4) O18 0.034(4) 0.059(4) 0.034(4) -0.008(3) -0.007(3) -0.006(3) N14 0.034(5) 0.045(5) 0.024(4) 0.006(3) -0.005(3) -0.014(4) C74 0.046(7) 0.058(7) 0.027(5) 0.002(5) -0.006(5) -0.017(5) C75 0.052(7) 0.100(8) 0.031(5) 0.002(5) 0.011(5) -0.012(6) C76 0.061(7) 0.028(5) 0.038(6) 0.011(5) -0.003(5) -0.010(5) O19 0.120(7) 0.049(4) 0.061(4) -0.015(4) -0.034(4) -0.003(4) O20 0.056(4) 0.036(3) 0.038(3) 0.008(3) -0.006(3) -0.013(3) C77 0.066(8) 0.054(6) 0.037(5) 0.008(5) -0.010(5) 0.002(5) C78 0.051(8) 0.064(7) 0.055(6) 0.007(5) -0.023(6) -0.008(5) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C3 1.731(9) . ? Cl2 C5 1.739(9) . ? C1 C3 1.376(12) . ? C1 C4 1.427(11) . ? C1 C21 1.469(12) . ? C2 C5 1.419(12) . ? C2 C20 1.439(12) . ? C2 C4 1.459(11) . ? C3 C6 1.401(12) . ? C4 C7 1.392(12) . ? C5 C8 1.350(12) . ? C6 C9 1.389(12) . ? C7 C10 1.402(11) . ? C7 C9 1.432(12) . ? C8 C10 1.376(11) . ? C9 C11 1.443(12) . ? C10 C12 1.459(12) . ? C11 O1 1.211(10) . ? C11 N1 1.405(12) . ? C12 O2 1.228(11) . ? C12 N1 1.389(11) . ? N1 C13 1.486(12) . ? C13 C14 1.520(13) . ? C14 O3 1.230(13) . ? C14 N2 1.358(13) . ? N2 C15 1.451(11) . ? C15 C16 1.489(15) . ? C15 C17 1.496(16) . ? C17 O5B 1.272(17) . ? C17 O4A 1.278(16) . ? C17 O5A 1.288(14) . ? C17 O4B 1.291(19) . ? O5A C18A 1.484(16) . ? C18A C19A 1.41(2) . ? O5B C18B 1.48(2) . ? C18B C19B 1.42(2) . ? Cl3 C22 1.720(8) . ? Cl4 C24 1.717(9) . ? C20 C22 1.410(12) . ? C20 C23 1.443(11) . ? C21 C24 1.397(11) . ? C21 C23 1.473(11) . ? C22 C25 1.397(12) . ? C23 C26 1.388(12) . ? C24 C27 1.399(12) . ? C25 C28 1.391(10) . ? C26 C29 1.386(10) . ? C26 C28 1.415(11) . ? C27 C29 1.389(11) . ? C28 C30 1.469(12) . ? C29 C31 1.449(12) . ? C30 O6 1.217(10) . ? C30 N3 1.384(10) . ? C31 O7 1.197(9) . ? C31 N3 1.423(11) . ? N3 C32 1.444(11) . ? C32 C33 1.476(12) . ? C33 O8 1.245(10) . ? C33 N4 1.349(10) . ? N4 C34 1.444(10) . ? C34 C35 1.504(11) . ? C34 C36 1.514(11) . ? C36 O9 1.192(10) . ? C36 O10 1.322(11) . ? O10 C37 1.458(8) . ? C37 C38 1.502(13) . ? Cl5 C43 1.734(9) . ? Cl6 C45 1.725(9) . ? C41 C43 1.422(12) . ? C41 C61 1.450(12) . ? C41 C44 1.450(11) . ? C42 C45 1.389(12) . ? C42 C44 1.408(11) . ? C42 C60 1.475(12) . ? C43 C46 1.371(11) . ? C44 C47 1.415(12) . ? C45 C48 1.407(12) . ? C46 C49 1.357(11) . ? C47 C49 1.398(11) . ? C47 C50 1.419(11) . ? C48 C50 1.365(11) . ? C49 C51 1.489(12) . ? C50 C52 1.488(12) . ? C51 O11 1.209(9) . ? C51 N11 1.423(10) . ? C52 O12 1.201(10) . ? C52 N11 1.408(11) . ? N11 C53 1.430(10) . ? C53 C54 1.511(12) . ? C54 O13 1.235(12) . ? C54 N12 1.292(11) . ? N12 C55 1.468(11) . ? C55 C56 1.535(15) . ? C55 C57 1.544(15) . ? C57 O14 1.183(11) . ? C57 O15 1.316(10) . ? O15 C58 1.452(9) . ? C58 C59 1.484(12) . ? Cl7 C62 1.732(8) . ? Cl8 C64 1.731(9) . ? C60 C62 1.389(12) . ? C60 C63 1.427(11) . ? C61 C63 1.394(11) . ? C61 C64 1.418(11) . ? C62 C65 1.374(12) . ? C63 C66 1.406(12) . ? C64 C67 1.392(12) . ? C65 C68 1.343(10) . ? C66 C68 1.405(11) . ? C66 C69 1.437(10) . ? C67 C69 1.371(11) . ? C68 C70 1.482(12) . ? C69 C71 1.482(12) . ? C70 O16 1.219(10) . ? C70 N13 1.382(10) . ? C71 O17 1.219(9) . ? C71 N13 1.394(11) . ? N13 C72 1.458(11) . ? C72 C73 1.543(12) . ? C73 O18 1.202(11) . ? C73 N14 1.343(11) . ? N14 C74 1.458(11) . ? C74 C76 1.511(13) . ? C74 C75 1.527(12) . ? C76 O19 1.166(10) . ? C76 O20 1.349(11) . ? O20 C77 1.453(10) . ? C77 C78 1.472(12) . ? 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 C3 C1 C4 116.7(8) . . ? C3 C1 C21 126.1(8) . . ? C4 C1 C21 117.1(8) . . ? C5 C2 C20 128.0(8) . . ? C5 C2 C4 114.9(8) . . ? C20 C2 C4 117.1(8) . . ? C1 C3 C6 121.4(8) . . ? C1 C3 Cl1 123.6(7) . . ? C6 C3 Cl1 114.8(7) . . ? C7 C4 C1 120.0(8) . . ? C7 C4 C2 119.3(8) . . ? C1 C4 C2 120.7(8) . . ? C8 C5 C2 123.0(8) . . ? C8 C5 Cl2 116.7(7) . . ? C2 C5 Cl2 119.9(7) . . ? C9 C6 C3 121.9(8) . . ? C4 C7 C10 121.7(8) . . ? C4 C7 C9 121.0(8) . . ? C10 C7 C9 117.3(8) . . ? C5 C8 C10 121.9(8) . . ? C6 C9 C7 116.4(8) . . ? C6 C9 C11 120.5(9) . . ? C7 C9 C11 122.7(8) . . ? C8 C10 C7 118.1(8) . . ? C8 C10 C12 120.1(8) . . ? C7 C10 C12 121.7(8) . . ? O1 C11 N1 120.9(9) . . ? O1 C11 C9 123.7(9) . . ? N1 C11 C9 115.2(9) . . ? O2 C12 N1 119.5(9) . . ? O2 C12 C10 123.7(9) . . ? N1 C12 C10 116.8(9) . . ? C12 N1 C11 125.0(8) . . ? C12 N1 C13 115.6(8) . . ? C11 N1 C13 119.3(8) . . ? N1 C13 C14 108.8(8) . . ? O3 C14 N2 122.1(10) . . ? O3 C14 C13 125.1(10) . . ? N2 C14 C13 112.7(10) . . ? C14 N2 C15 121.4(10) . . ? N2 C15 C16 113.6(8) . . ? N2 C15 C17 110.5(10) . . ? C16 C15 C17 109.6(10) . . ? O5B C17 O4A 110(2) . . ? O4A C17 O5A 123.9(19) . . ? O5B C17 O4B 117(3) . . ? O5A C17 O4B 121(2) . . ? O5B C17 C15 124(2) . . ? O4A C17 C15 124.4(14) . . ? O5A C17 C15 111.6(15) . . ? O4B C17 C15 119.3(19) . . ? C17 O5A C18A 119(2) . . ? C19A C18A O5A 107.6(17) . . ? C17 O5B C18B 120(3) . . ? C19B C18B O5B 108(2) . . ? C22 C20 C2 125.9(8) . . ? C22 C20 C23 115.5(8) . . ? C2 C20 C23 118.6(8) . . ? C24 C21 C1 127.6(8) . . ? C24 C21 C23 115.5(8) . . ? C1 C21 C23 116.8(7) . . ? C25 C22 C20 122.3(8) . . ? C25 C22 Cl3 115.2(7) . . ? C20 C22 Cl3 122.4(7) . . ? C26 C23 C20 122.1(8) . . ? C26 C23 C21 118.7(7) . . ? C20 C23 C21 119.1(8) . . ? C21 C24 C27 122.1(8) . . ? C21 C24 Cl4 122.1(7) . . ? C27 C24 Cl4 115.7(6) . . ? C28 C25 C22 119.6(8) . . ? C29 C26 C23 121.8(8) . . ? C29 C26 C28 119.4(9) . . ? C23 C26 C28 118.8(7) . . ? C29 C27 C24 120.2(8) . . ? C25 C28 C26 120.6(8) . . ? C25 C28 C30 118.7(8) . . ? C26 C28 C30 120.3(8) . . ? C26 C29 C27 119.1(8) . . ? C26 C29 C31 122.1(8) . . ? C27 C29 C31 118.8(8) . . ? O6 C30 N3 119.6(8) . . ? O6 C30 C28 122.8(8) . . ? N3 C30 C28 117.6(8) . . ? O7 C31 N3 119.3(9) . . ? O7 C31 C29 124.2(9) . . ? N3 C31 C29 116.5(8) . . ? C30 N3 C31 123.4(8) . . ? C30 N3 C32 118.0(8) . . ? C31 N3 C32 118.2(7) . . ? N3 C32 C33 113.7(8) . . ? O8 C33 N4 123.4(8) . . ? O8 C33 C32 121.0(8) . . ? N4 C33 C32 115.6(8) . . ? C33 N4 C34 121.0(7) . . ? N4 C34 C35 109.2(8) . . ? N4 C34 C36 113.3(7) . . ? C35 C34 C36 111.4(7) . . ? O9 C36 O10 123.2(9) . . ? O9 C36 C34 124.2(9) . . ? O10 C36 C34 112.2(9) . . ? C36 O10 C37 117.5(7) . . ? O10 C37 C38 106.7(7) . . ? C43 C41 C61 128.2(8) . . ? C43 C41 C44 115.6(8) . . ? C61 C41 C44 116.2(8) . . ? C45 C42 C44 117.6(9) . . ? C45 C42 C60 124.8(8) . . ? C44 C42 C60 117.6(8) . . ? C46 C43 C41 122.8(8) . . ? C46 C43 Cl5 116.6(7) . . ? C41 C43 Cl5 120.5(7) . . ? C42 C44 C47 120.9(8) . . ? C42 C44 C41 120.3(9) . . ? C47 C44 C41 118.8(8) . . ? C42 C45 C48 121.1(8) . . ? C42 C45 Cl6 123.9(7) . . ? C48 C45 Cl6 114.8(7) . . ? C49 C46 C43 119.6(8) . . ? C49 C47 C44 119.9(8) . . ? C49 C47 C50 122.6(9) . . ? C44 C47 C50 117.4(8) . . ? C50 C48 C45 119.7(8) . . ? C46 C49 C47 121.4(9) . . ? C46 C49 C51 119.2(8) . . ? C47 C49 C51 119.3(8) . . ? C48 C50 C47 121.4(9) . . ? C48 C50 C52 119.2(8) . . ? C47 C50 C52 119.2(8) . . ? O11 C51 N11 119.9(8) . . ? O11 C51 C49 122.8(8) . . ? N11 C51 C49 117.3(7) . . ? O12 C52 N11 120.1(9) . . ? O12 C52 C50 122.6(9) . . ? N11 C52 C50 117.3(8) . . ? C52 N11 C51 124.2(8) . . ? C52 N11 C53 115.6(7) . . ? C51 N11 C53 120.1(7) . . ? N11 C53 C54 113.2(8) . . ? O13 C54 N12 124.4(10) . . ? O13 C54 C53 118.6(9) . . ? N12 C54 C53 117.0(10) . . ? C54 N12 C55 122.4(10) . . ? N12 C55 C56 108.4(10) . . ? N12 C55 C57 113.7(7) . . ? C56 C55 C57 109.6(9) . . ? O14 C57 O15 127.9(9) . . ? O14 C57 C55 120.7(9) . . ? O15 C57 C55 111.2(9) . . ? C57 O15 C58 115.3(7) . . ? O15 C58 C59 105.5(7) . . ? C62 C60 C63 116.6(9) . . ? C62 C60 C42 127.0(8) . . ? C63 C60 C42 116.4(8) . . ? C63 C61 C64 117.3(8) . . ? C63 C61 C41 118.4(7) . . ? C64 C61 C41 124.3(8) . . ? C65 C62 C60 121.6(8) . . ? C65 C62 Cl7 116.6(7) . . ? C60 C62 Cl7 121.6(7) . . ? C61 C63 C66 120.5(7) . . ? C61 C63 C60 121.1(8) . . ? C66 C63 C60 118.4(8) . . ? C67 C64 C61 121.3(8) . . ? C67 C64 Cl8 114.5(6) . . ? C61 C64 Cl8 124.2(7) . . ? C68 C65 C62 122.4(8) . . ? C68 C66 C63 121.0(7) . . ? C68 C66 C69 119.7(8) . . ? C63 C66 C69 119.1(8) . . ? C69 C67 C64 120.1(8) . . ? C65 C68 C66 118.0(8) . . ? C65 C68 C70 121.5(8) . . ? C66 C68 C70 120.4(8) . . ? C67 C69 C66 119.5(8) . . ? C67 C69 C71 120.3(8) . . ? C66 C69 C71 120.2(8) . . ? O16 C70 N13 120.7(9) . . ? O16 C70 C68 121.7(8) . . ? N13 C70 C68 117.6(8) . . ? O17 C71 N13 121.4(9) . . ? O17 C71 C69 121.8(9) . . ? N13 C71 C69 116.8(8) . . ? C70 N13 C71 125.3(8) . . ? C70 N13 C72 115.9(8) . . ? C71 N13 C72 118.8(7) . . ? N13 C72 C73 110.5(8) . . ? O18 C73 N14 124.8(8) . . ? O18 C73 C72 123.7(9) . . ? N14 C73 C72 111.5(9) . . ? C73 N14 C74 121.3(8) . . ? N14 C74 C76 109.9(8) . . ? N14 C74 C75 107.8(8) . . ? C76 C74 C75 111.1(8) . . ? O19 C76 O20 124.9(9) . . ? O19 C76 C74 125.6(10) . . ? O20 C76 C74 109.5(8) . . ? C76 O20 C77 116.0(7) . . ? O20 C77 C78 108.7(7) . . ? 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 C1 C21 C24 -30.5(16) . . . . ? C5 C2 C20 C22 -32.2(16) . . . . ? C43 C41 C61 C64 33.8(16) . . . . ? C45 C42 C60 C62 31.6(15) . . . . ? _diffrn_measured_fraction_theta_max 0.966 _diffrn_reflns_theta_full 25.25 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.426 _refine_diff_density_min -0.423 _refine_diff_density_rms 0.097 # Attachment 'cl176-150K.cif' data_PDI-Cl4-[Gly-Val(OEt)]2-150K _database_code_depnum_ccdc_archive 'CCDC 833910' #TrackingRef 'cl176-150K.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_compound_source 'synthesis as described' _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C42 H36 Cl4 N4 O10' _chemical_formula_sum 'C42 H36 Cl4 N4 O10' _chemical_formula_weight 898.55 _chemical_absolute_configuration rm 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' 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 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' 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' _cell_length_a 10.019(2) _cell_length_b 16.372(3) _cell_length_c 49.573(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 8132(3) _cell_formula_units_Z 8 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2 _cell_measurement_theta_max 26 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.468 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3712 _exptl_absorpt_coefficient_mu 0.356 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.70 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Nonius KappaCCD' _diffrn_measurement_method 'combined \f and \w-scans' _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_detector_area_resol_mean 9 _diffrn_standards_decay_% ? _diffrn_reflns_number 44150 _diffrn_reflns_av_R_equivalents 0.0686 _diffrn_reflns_av_sigmaI/netI 0.1087 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -61 _diffrn_reflns_limit_l_max 55 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 26.06 _reflns_number_total 11623 _reflns_number_gt 7584 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND 3.1 (Crystal Impact GbR 2005)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^ > 2\s(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^)+(0.0498P)^2^+15.7054P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.03(8) _refine_ls_number_reflns 11623 _refine_ls_number_parameters 1095 _refine_ls_number_restraints 78 _refine_ls_R_factor_all 0.1297 _refine_ls_R_factor_gt 0.0642 _refine_ls_wR_factor_ref 0.1387 _refine_ls_wR_factor_gt 0.1241 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.035 _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 0.69955(17) 0.79079(10) 0.81225(3) 0.0204(4) Uani 1 1 d . . . Cl2 Cl 0.47187(19) 0.33797(10) 0.83768(3) 0.0268(5) Uani 1 1 d . . . Cl3 Cl 0.61700(18) 0.34430(10) 0.78277(3) 0.0231(4) Uani 1 1 d . . . Cl4 Cl 0.40564(17) 0.79295(10) 0.82051(3) 0.0216(4) Uani 1 1 d . . . C1 C 0.6047(7) 0.6393(4) 0.82412(12) 0.0172(17) Uani 1 1 d . . . C2 C 0.5750(6) 0.4891(4) 0.82638(11) 0.0124(16) Uani 1 1 d U . . C3 C 0.6841(7) 0.7034(4) 0.83145(12) 0.0160(17) Uani 1 1 d . . . C4 C 0.6284(6) 0.5628(4) 0.83716(12) 0.0156(16) Uani 1 1 d . . . C5 C 0.5710(7) 0.4226(4) 0.84370(13) 0.0167(17) Uani 1 1 d . . . C6 C 0.7711(7) 0.7000(5) 0.85363(13) 0.0243(19) Uani 1 1 d . . . H6 H 0.8227 0.7452 0.8582 0.029 Uiso 1 1 calc R . . C7 C 0.7080(7) 0.5594(4) 0.86059(12) 0.0181(18) Uani 1 1 d . . . C8 C 0.6428(7) 0.4220(4) 0.86819(12) 0.0232(19) Uani 1 1 d . . . H8 H 0.6411 0.3755 0.8790 0.028 Uiso 1 1 calc R . . C9 C 0.7796(7) 0.6295(4) 0.86858(12) 0.0175(18) Uani 1 1 d . . . C10 C 0.7132(7) 0.4871(4) 0.87612(12) 0.0188(17) Uani 1 1 d . . . C11 C 0.8686(8) 0.6273(5) 0.89272(13) 0.024(2) Uani 1 1 d . . . C12 C 0.7912(8) 0.4856(5) 0.90179(13) 0.0269(19) Uani 1 1 d . . . N1 N 0.8701(6) 0.5530(4) 0.90727(11) 0.0263(16) Uani 1 1 d . . . O1 O 0.9358(5) 0.6844(3) 0.89957(9) 0.0328(14) Uani 1 1 d . . . O2 O 0.7874(6) 0.4292(3) 0.91723(9) 0.0425(15) Uani 1 1 d . . . C13 C 0.9411(8) 0.5544(5) 0.93320(13) 0.033(2) Uani 1 1 d . . . H13A H 1.0186 0.5897 0.9320 0.039 Uiso 1 1 calc R . . H13B H 0.9709 0.4998 0.9379 0.039 Uiso 1 1 calc R . . C14 C 0.8438(8) 0.5866(5) 0.95470(13) 0.0247(19) Uani 1 1 d . . . O3 O 0.7385(5) 0.6164(3) 0.94876(10) 0.0374(15) Uani 1 1 d . . . N2 N 0.8862(6) 0.5784(3) 0.98021(11) 0.0332(16) Uani 1 1 d . . . H2 H 0.8323 0.5947 0.9926 0.040 Uiso 1 1 calc R . . C15 C 1.0135(8) 0.5449(5) 0.98938(14) 0.036(2) Uani 1 1 d . . . H15 H 1.0809 0.5604 0.9760 0.044 Uiso 1 1 calc R . . C16 C 1.0571(8) 0.5824(5) 1.01651(14) 0.046(2) Uani 1 1 d . . . H16 H 1.1432 0.5580 1.0213 0.055 Uiso 1 1 calc R . . C17 C 1.0802(9) 0.6751(6) 1.01299(17) 0.063(3) Uani 1 1 d . . . H17A H 1.1380 0.6843 0.9978 0.094 Uiso 1 1 calc R . . H17B H 1.1209 0.6968 1.0290 0.094 Uiso 1 1 calc R . . H17C H 0.9963 0.7018 1.0099 0.094 Uiso 1 1 calc R . . C18 C 0.9593(9) 0.5628(7) 1.03963(14) 0.072(3) Uani 1 1 d . . . H18A H 0.8767 0.5912 1.0367 0.109 Uiso 1 1 calc R . . H18B H 0.9974 0.5799 1.0565 0.109 Uiso 1 1 calc R . . H18C H 0.9429 0.5050 1.0401 0.109 Uiso 1 1 calc R . . C19 C 1.0156(11) 0.4518(6) 0.99142(15) 0.043(2) Uani 1 1 d . . . O4 O 1.1132(7) 0.4142(4) 0.99867(14) 0.077(2) Uani 1 1 d . . . O5 O 0.9057(6) 0.4180(3) 0.98189(10) 0.0474(15) Uani 1 1 d . . . C20 C 0.9071(11) 0.3278(5) 0.97914(19) 0.067(3) Uani 1 1 d . . . H20A H 0.9697 0.3116 0.9652 0.080 Uiso 1 1 calc R . . H20B H 0.9345 0.3028 0.9960 0.080 Uiso 1 1 calc R . . C21 C 0.7710(10) 0.3008(6) 0.9719(2) 0.070(3) Uani 1 1 d . . . H21A H 0.7120 0.3104 0.9869 0.105 Uiso 1 1 calc R . . H21B H 0.7722 0.2435 0.9678 0.105 Uiso 1 1 calc R . . H21C H 0.7404 0.3308 0.9565 0.105 Uiso 1 1 calc R . . C22 C 0.5183(7) 0.4923(4) 0.79892(12) 0.0155(17) Uani 1 1 d . . . C23 C 0.4959(7) 0.6427(4) 0.80461(12) 0.0177(18) Uani 1 1 d . . . C24 C 0.5156(6) 0.4286(4) 0.78030(12) 0.0155(16) Uani 1 1 d U . . C25 C 0.4641(7) 0.5686(4) 0.79049(11) 0.0144(17) Uani 1 1 d . . . C26 C 0.4166(7) 0.7096(4) 0.79926(13) 0.0167(17) Uani 1 1 d . . . C27 C 0.4351(7) 0.4328(4) 0.75703(12) 0.0189(18) Uani 1 1 d . . . H27 H 0.4326 0.3885 0.7453 0.023 Uiso 1 1 calc R . . C28 C 0.3816(7) 0.5720(4) 0.76777(12) 0.0155(17) Uani 1 1 d U . . C29 C 0.3285(7) 0.7120(4) 0.77704(12) 0.0142(17) Uani 1 1 d U . . H29 H 0.2800 0.7591 0.7733 0.017 Uiso 1 1 calc R . . C30 C 0.3600(7) 0.5013(4) 0.75136(12) 0.0130(16) Uani 1 1 d U . . C31 C 0.3157(7) 0.6461(4) 0.76150(12) 0.0118(16) Uani 1 1 d U . . C32 C 0.2680(7) 0.5039(4) 0.72857(12) 0.0191(18) Uani 1 1 d . . . C33 C 0.2240(7) 0.6482(5) 0.73821(13) 0.0164(17) Uani 1 1 d U . . N3 N 0.1994(6) 0.5765(4) 0.72416(10) 0.0197(15) Uani 1 1 d . . . O6 O 0.2493(5) 0.4449(3) 0.71400(9) 0.0292(13) Uani 1 1 d . . . O7 O 0.1629(5) 0.7109(3) 0.73158(9) 0.0235(12) Uani 1 1 d . . . C34 C 0.1042(8) 0.5811(4) 0.70249(12) 0.027(2) Uani 1 1 d . . . H34A H 0.0248 0.6092 0.7087 0.032 Uiso 1 1 calc R . . H34B H 0.0785 0.5263 0.6972 0.032 Uiso 1 1 calc R . . C35 C 0.1608(11) 0.6261(4) 0.67810(15) 0.035(2) Uani 1 1 d . . . O8 O 0.2794(6) 0.6369(3) 0.67513(10) 0.0415(15) Uani 1 1 d . . . N4 N 0.0604(7) 0.6526(4) 0.66147(12) 0.0415(18) Uani 1 1 d . . . H4 H -0.0211 0.6415 0.6655 0.050 Uiso 1 1 calc R . . C36 C 0.0887(9) 0.6993(5) 0.63705(14) 0.048(2) Uani 1 1 d . . . H36 H 0.1707 0.7310 0.6397 0.058 Uiso 1 1 calc R . . C37 C 0.1069(10) 0.6419(7) 0.61241(16) 0.064(3) Uani 1 1 d . . . H37 H 0.1813 0.6054 0.6167 0.077 Uiso 1 1 calc R . . C38 C -0.0120(12) 0.5882(6) 0.60681(18) 0.073(3) Uani 1 1 d . . . H38A H -0.0876 0.6216 0.6024 0.109 Uiso 1 1 calc R . . H38B H -0.0317 0.5561 0.6225 0.109 Uiso 1 1 calc R . . H38C H 0.0077 0.5526 0.5919 0.109 Uiso 1 1 calc R . . C39 C 0.1501(9) 0.6921(7) 0.58761(17) 0.074(3) Uani 1 1 d . . . H39A H 0.0761 0.7241 0.5813 0.110 Uiso 1 1 calc R . . H39B H 0.1787 0.6557 0.5735 0.110 Uiso 1 1 calc R . . H39C H 0.2224 0.7276 0.5925 0.110 Uiso 1 1 calc R . . C40 C -0.0282(13) 0.7580(6) 0.63260(18) 0.051(3) Uani 1 1 d . . . O9 O -0.1425(8) 0.7427(4) 0.63589(15) 0.075(2) Uani 1 1 d . . . O10 O 0.0161(7) 0.8319(4) 0.62520(11) 0.0642(19) Uani 1 1 d . . . C41 C -0.0959(10) 0.8904(6) 0.61893(18) 0.066(3) Uani 1 1 d . . . H41A H -0.1638 0.8854 0.6328 0.080 Uiso 1 1 calc R . . H41B H -0.0616 0.9457 0.6196 0.080 Uiso 1 1 calc R . . C42 C -0.1582(12) 0.8765(6) 0.59232(17) 0.081(4) Uani 1 1 d . . . H42A H -0.0915 0.8805 0.5785 0.121 Uiso 1 1 calc R . . H42B H -0.2259 0.9170 0.5893 0.121 Uiso 1 1 calc R . . H42C H -0.1977 0.8231 0.5919 0.121 Uiso 1 1 calc R . . Cl5 Cl 0.90836(17) 0.44369(10) 0.81999(3) 0.0201(4) Uani 1 1 d . . . Cl6 Cl 1.10755(18) 0.89434(10) 0.78245(3) 0.0235(4) Uani 1 1 d . . . Cl7 Cl 0.96596(18) 0.90144(10) 0.83789(3) 0.0261(5) Uani 1 1 d . . . Cl8 Cl 1.20292(17) 0.44935(10) 0.81035(3) 0.0203(4) Uani 1 1 d . . . C51 C 0.9925(7) 0.5953(4) 0.80404(12) 0.0137(16) Uani 1 1 d U . . C52 C 1.0129(6) 0.7459(4) 0.79841(12) 0.0144(16) Uani 1 1 d U . . C53 C 0.9144(7) 0.5267(4) 0.79834(12) 0.0166(17) Uani 1 1 d . . . C54 C 0.9609(7) 0.6689(4) 0.78972(12) 0.0160(17) Uani 1 1 d . . . C55 C 1.0053(7) 0.8094(4) 0.77984(13) 0.0169(17) Uani 1 1 d . . . C56 C 0.8289(7) 0.5232(4) 0.77656(13) 0.0188(18) Uani 1 1 d . . . H56 H 0.7843 0.4749 0.7725 0.023 Uiso 1 1 calc R . . C57 C 0.8739(7) 0.6658(4) 0.76739(12) 0.0149(17) Uani 1 1 d . . . C58 C 0.9268(6) 0.8056(4) 0.75705(12) 0.0142(17) Uani 1 1 d . . . H58 H 0.9239 0.8496 0.7452 0.017 Uiso 1 1 calc R . . C59 C 0.8099(7) 0.5925(4) 0.76062(12) 0.0186(18) Uani 1 1 d . . . C60 C 0.8527(7) 0.7366(4) 0.75183(12) 0.0154(17) Uani 1 1 d U . . C61 C 0.7161(7) 0.5875(5) 0.73786(12) 0.0172(17) Uani 1 1 d . . . C62 C 0.7570(7) 0.7346(5) 0.72927(13) 0.0203(18) Uani 1 1 d U . . N11 N 0.6859(6) 0.6621(3) 0.72539(10) 0.0208(15) Uani 1 1 d . . . O11 O 0.6649(5) 0.5251(3) 0.73066(9) 0.0265(13) Uani 1 1 d . . . O12 O 0.7338(5) 0.7935(3) 0.71533(9) 0.0293(13) Uani 1 1 d . . . C63 C 0.5891(7) 0.6585(4) 0.70365(12) 0.0222(18) Uani 1 1 d . . . H63A H 0.5489 0.7118 0.7011 0.027 Uiso 1 1 calc R . . H63B H 0.5189 0.6201 0.7082 0.027 Uiso 1 1 calc R . . C64 C 0.6575(8) 0.6317(4) 0.67758(14) 0.0212(18) Uani 1 1 d . . . O13 O 0.7727(6) 0.6151(3) 0.67653(10) 0.0316(13) Uani 1 1 d . . . N12 N 0.5731(6) 0.6278(3) 0.65652(11) 0.0284(16) Uani 1 1 d . . . H12 H 0.4904 0.6397 0.6589 0.034 Uiso 1 1 calc R . . C65 C 0.6179(9) 0.6040(4) 0.62991(13) 0.036(2) Uani 1 1 d . . . H65 H 0.7156 0.6062 0.6298 0.043 Uiso 1 1 calc R . . C66 C 0.5762(9) 0.5168(5) 0.62228(15) 0.040(2) Uani 1 1 d . . . H66 H 0.6219 0.5029 0.6054 0.048 Uiso 1 1 calc R . . C67 C 0.6245(10) 0.4575(5) 0.64366(15) 0.055(3) Uani 1 1 d . . . H67A H 0.5743 0.4655 0.6599 0.083 Uiso 1 1 calc R . . H67B H 0.7174 0.4669 0.6472 0.083 Uiso 1 1 calc R . . H67C H 0.6121 0.4025 0.6374 0.083 Uiso 1 1 calc R . . C68 C 0.4289(9) 0.5093(5) 0.61729(19) 0.060(3) Uani 1 1 d . . . H68A H 0.4056 0.4527 0.6156 0.090 Uiso 1 1 calc R . . H68B H 0.4061 0.5376 0.6010 0.090 Uiso 1 1 calc R . . H68C H 0.3809 0.5328 0.6321 0.090 Uiso 1 1 calc R . . C69 C 0.5677(11) 0.6650(5) 0.60968(16) 0.047(3) Uani 1 1 d . . . O14 O 0.4739(7) 0.7085(4) 0.61196(10) 0.0522(16) Uani 1 1 d . . . O15 O 0.6404(6) 0.6565(3) 0.58686(11) 0.0540(17) Uani 1 1 d . . . C70 C 0.6048(11) 0.7113(6) 0.56484(16) 0.072(3) Uani 1 1 d . . . H70A H 0.5922 0.7666 0.5714 0.086 Uiso 1 1 calc R . . H70B H 0.5236 0.6933 0.5560 0.086 Uiso 1 1 calc R . . C71 C 0.7266(10) 0.7065(7) 0.54516(18) 0.077(3) Uani 1 1 d . . . H71A H 0.8070 0.7193 0.5548 0.115 Uiso 1 1 calc R . . H71B H 0.7145 0.7449 0.5307 0.115 Uiso 1 1 calc R . . H71C H 0.7330 0.6523 0.5379 0.115 Uiso 1 1 calc R . . C72 C 1.0666(7) 0.7492(4) 0.82605(12) 0.0147(16) Uani 1 1 d . . . C73 C 1.1028(7) 0.6001(4) 0.82348(11) 0.0142(16) Uani 1 1 d . . . C74 C 1.0648(7) 0.8169(4) 0.84358(13) 0.0246(18) Uani 1 1 d . . . C75 C 1.1235(6) 0.6760(4) 0.83641(12) 0.0141(16) Uani 1 1 d . . . C76 C 1.1884(7) 0.5360(4) 0.83001(12) 0.0151(17) Uani 1 1 d U . . C77 C 1.1350(7) 0.8162(4) 0.86784(13) 0.0186(18) Uani 1 1 d . . . H77 H 1.1314 0.8617 0.8791 0.022 Uiso 1 1 calc R . . C78 C 1.2020(7) 0.6785(4) 0.86013(13) 0.0152(17) Uani 1 1 d . . . C79 C 1.2733(7) 0.5414(4) 0.85232(13) 0.0199(18) Uani 1 1 d . . . H79 H 1.3287 0.4977 0.8566 0.024 Uiso 1 1 calc R . . C80 C 1.2089(7) 0.7502(4) 0.87542(12) 0.0177(18) Uani 1 1 d . . . C81 C 1.2759(7) 0.6100(4) 0.86785(12) 0.0171(17) Uani 1 1 d . . . C82 C 1.2886(8) 0.7542(5) 0.89990(14) 0.0254(19) Uani 1 1 d U . . C83 C 1.3619(7) 0.6129(5) 0.89187(15) 0.023(2) Uani 1 1 d . . . N13 N 1.3650(6) 0.6860(3) 0.90615(10) 0.0198(15) Uani 1 1 d . . . O16 O 1.2947(6) 0.8154(3) 0.91406(9) 0.0399(15) Uani 1 1 d . . . O17 O 1.4307(5) 0.5556(3) 0.89899(9) 0.0314(13) Uani 1 1 d . . . C84 C 1.4448(8) 0.6859(4) 0.93041(13) 0.032(2) Uani 1 1 d . . . H84A H 1.4500 0.7410 0.9375 0.038 Uiso 1 1 calc R . . H84B H 1.5346 0.6680 0.9261 0.038 Uiso 1 1 calc R . . C85 C 1.3844(10) 0.6290(4) 0.95186(13) 0.026(2) Uani 1 1 d . . . O18 O 1.2670(6) 0.6130(3) 0.95229(10) 0.0416(15) Uani 1 1 d . . . N14 N 1.4764(6) 0.6026(3) 0.96936(11) 0.0309(16) Uani 1 1 d . . . H14 H 1.5579 0.6173 0.9670 0.037 Uiso 1 1 calc R . . C86 C 1.4459(8) 0.5507(5) 0.99199(13) 0.034(2) Uani 1 1 d . . . H86 H 1.3488 0.5481 0.9942 0.040 Uiso 1 1 calc R . . C87 C 1.4993(8) 0.4644(5) 0.98843(14) 0.037(2) Uani 1 1 d . . . H87 H 1.5966 0.4676 0.9866 0.044 Uiso 1 1 calc R . . C88 C 1.4431(10) 0.4252(5) 0.96286(16) 0.062(3) Uani 1 1 d . . . H88A H 1.4786 0.3710 0.9610 0.093 Uiso 1 1 calc R . . H88B H 1.4679 0.4574 0.9475 0.093 Uiso 1 1 calc R . . H88C H 1.3476 0.4226 0.9641 0.093 Uiso 1 1 calc R . . C89 C 1.4679(10) 0.4130(5) 1.01261(17) 0.059(3) Uani 1 1 d . . . H89A H 1.5145 0.4341 1.0280 0.088 Uiso 1 1 calc R . . H89B H 1.4955 0.3578 1.0093 0.088 Uiso 1 1 calc R . . H89C H 1.3735 0.4143 1.0160 0.088 Uiso 1 1 calc R . . C90 C 1.5062(10) 0.5906(5) 1.01663(15) 0.039(2) Uani 1 1 d . . . O19 O 1.6228(6) 0.6062(4) 1.01845(10) 0.0452(15) Uani 1 1 d . . . O20 O 1.4176(5) 0.6029(3) 1.03592(10) 0.0475(15) Uani 1 1 d . . . C91 C 1.4650(10) 0.6394(6) 1.06109(15) 0.063(3) Uani 1 1 d . . . H91A H 1.4877 0.6964 1.0584 0.076 Uiso 1 1 calc R . . H91B H 1.5432 0.6108 1.0677 0.076 Uiso 1 1 calc R . . C92 C 1.3521(10) 0.6313(6) 1.08053(16) 0.064(3) Uani 1 1 d . . . H92A H 1.2714 0.6506 1.0723 0.095 Uiso 1 1 calc R . . H92B H 1.3707 0.6630 1.0964 0.095 Uiso 1 1 calc R . . H92C H 1.3416 0.5749 1.0855 0.095 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 0.0210(11) 0.0137(10) 0.0264(9) 0.0014(7) 0.0017(8) -0.0042(9) Cl2 0.0333(12) 0.0177(10) 0.0295(9) 0.0030(8) -0.0037(9) -0.0084(10) Cl3 0.0240(11) 0.0127(10) 0.0326(9) -0.0019(8) -0.0020(9) 0.0047(9) Cl4 0.0209(11) 0.0168(10) 0.0272(9) -0.0041(7) 0.0040(9) 0.0006(9) C1 0.021(5) 0.014(4) 0.017(3) -0.006(3) -0.001(4) 0.009(4) C2 0.013(3) 0.010(3) 0.014(2) 0.002(2) 0.000(2) -0.001(2) C3 0.016(4) 0.018(4) 0.014(3) -0.003(3) -0.002(3) 0.002(4) C4 0.013(4) 0.015(4) 0.020(3) -0.002(3) 0.006(3) 0.002(4) C5 0.012(4) 0.008(4) 0.030(4) -0.003(3) -0.001(3) -0.003(4) C6 0.030(5) 0.019(5) 0.025(4) -0.001(3) 0.009(4) 0.002(4) C7 0.028(5) 0.011(4) 0.015(3) -0.002(3) 0.001(4) 0.005(4) C8 0.037(5) 0.016(4) 0.016(4) 0.008(3) 0.005(4) 0.010(4) C9 0.018(4) 0.019(5) 0.015(3) -0.003(3) 0.004(3) -0.006(4) C10 0.016(4) 0.018(5) 0.023(4) -0.002(3) -0.002(4) 0.003(4) C11 0.028(5) 0.026(5) 0.017(4) 0.000(3) -0.001(4) -0.005(5) C12 0.035(5) 0.027(5) 0.019(4) -0.001(4) 0.000(4) -0.014(5) N1 0.027(4) 0.029(4) 0.023(3) 0.002(3) -0.005(3) -0.001(4) O1 0.035(4) 0.039(3) 0.024(3) -0.002(2) -0.008(3) -0.017(3) O2 0.066(4) 0.038(3) 0.024(3) 0.010(3) -0.013(3) -0.014(3) C13 0.037(5) 0.033(5) 0.028(4) 0.002(4) -0.015(4) -0.005(5) C14 0.027(5) 0.032(5) 0.015(4) 0.000(3) -0.004(4) -0.003(4) O3 0.021(3) 0.058(4) 0.033(3) 0.000(3) -0.001(3) 0.006(3) N2 0.035(4) 0.044(4) 0.021(3) -0.007(3) 0.002(3) 0.007(4) C15 0.035(6) 0.044(6) 0.031(4) -0.002(4) -0.004(4) 0.005(5) C16 0.032(5) 0.079(7) 0.027(4) -0.016(4) -0.010(4) 0.017(5) C17 0.053(7) 0.077(8) 0.058(6) -0.044(5) -0.011(5) 0.017(6) C18 0.051(6) 0.145(10) 0.021(4) -0.001(5) -0.006(5) 0.021(7) C19 0.046(7) 0.057(7) 0.025(4) 0.008(4) -0.007(4) -0.008(6) O4 0.058(5) 0.072(5) 0.102(6) 0.005(4) -0.010(4) 0.041(4) O5 0.052(4) 0.049(4) 0.041(3) 0.004(3) -0.008(3) -0.003(4) C20 0.094(9) 0.040(7) 0.066(6) 0.014(5) 0.022(7) 0.015(6) C21 0.072(8) 0.061(7) 0.078(7) 0.003(5) -0.011(6) -0.013(7) C22 0.009(4) 0.014(4) 0.024(4) 0.001(3) 0.003(3) -0.006(4) C23 0.026(5) 0.012(4) 0.015(3) -0.006(3) 0.005(3) -0.004(4) C24 0.014(3) 0.011(3) 0.022(2) 0.002(2) 0.002(2) 0.000(2) C25 0.018(4) 0.014(4) 0.011(3) -0.003(3) 0.008(3) 0.000(4) C26 0.026(5) 0.005(4) 0.020(4) -0.004(3) 0.003(4) -0.004(4) C27 0.026(5) 0.011(4) 0.019(4) -0.007(3) 0.001(3) -0.003(4) C28 0.016(3) 0.010(3) 0.020(3) -0.001(2) 0.000(2) 0.000(2) C29 0.016(3) 0.008(3) 0.018(3) 0.000(2) -0.001(2) 0.002(2) C30 0.008(3) 0.013(3) 0.018(2) -0.003(2) 0.001(2) -0.001(2) C31 0.010(3) 0.012(3) 0.014(2) -0.001(2) 0.003(2) -0.001(2) C32 0.024(5) 0.014(5) 0.019(3) -0.003(3) 0.000(3) -0.004(4) C33 0.015(3) 0.016(3) 0.018(2) -0.003(2) 0.001(2) -0.005(2) N3 0.021(4) 0.020(4) 0.018(3) -0.002(3) -0.006(3) -0.001(3) O6 0.037(3) 0.021(3) 0.029(3) -0.008(2) -0.011(3) 0.002(3) O7 0.020(3) 0.020(3) 0.030(3) 0.003(2) -0.008(2) 0.006(3) C34 0.033(5) 0.028(5) 0.020(4) -0.003(3) -0.006(4) -0.011(4) C35 0.057(7) 0.022(5) 0.026(4) 0.002(3) -0.008(5) -0.001(5) O8 0.032(4) 0.062(4) 0.031(3) 0.003(3) 0.002(3) -0.015(3) N4 0.031(4) 0.060(5) 0.033(4) 0.018(4) -0.002(3) -0.001(4) C36 0.046(6) 0.070(6) 0.029(4) 0.011(4) 0.011(4) -0.015(6) C37 0.053(7) 0.108(9) 0.032(5) 0.018(5) -0.004(5) 0.033(7) C38 0.113(10) 0.055(6) 0.050(6) -0.002(5) -0.013(6) 0.012(7) C39 0.048(7) 0.127(10) 0.046(6) 0.030(6) -0.003(5) -0.006(7) C40 0.068(8) 0.029(6) 0.056(6) 0.013(4) -0.005(6) 0.010(7) O9 0.057(5) 0.077(5) 0.090(5) 0.020(4) -0.013(5) 0.011(5) O10 0.086(5) 0.049(4) 0.058(4) 0.002(3) 0.022(4) -0.007(4) C41 0.069(7) 0.060(7) 0.070(7) -0.003(5) 0.006(6) 0.041(6) C42 0.124(10) 0.078(8) 0.041(6) 0.008(5) -0.008(6) 0.033(7) Cl5 0.0181(10) 0.0169(10) 0.0253(9) 0.0064(7) -0.0023(8) -0.0004(9) Cl6 0.0238(11) 0.0148(10) 0.0319(10) 0.0025(8) -0.0024(9) -0.0026(9) Cl7 0.0295(12) 0.0162(10) 0.0327(10) -0.0062(8) -0.0023(9) 0.0017(10) Cl8 0.0188(11) 0.0157(10) 0.0265(9) -0.0002(8) -0.0005(8) 0.0034(9) C51 0.012(3) 0.012(3) 0.016(2) 0.000(2) 0.004(2) -0.005(2) C52 0.012(3) 0.013(3) 0.018(2) -0.001(2) -0.003(2) -0.004(2) C53 0.023(5) 0.010(4) 0.016(3) 0.003(3) -0.005(3) 0.009(4) C54 0.022(5) 0.014(4) 0.013(3) -0.002(3) 0.002(3) -0.004(4) C55 0.012(4) 0.011(4) 0.027(4) -0.007(3) 0.002(3) 0.000(3) C56 0.018(4) 0.008(4) 0.030(4) -0.002(3) 0.009(4) 0.002(4) C57 0.010(4) 0.020(4) 0.015(3) -0.004(3) -0.002(3) -0.005(4) C58 0.021(4) 0.009(4) 0.013(3) 0.004(3) 0.004(3) 0.004(4) C59 0.024(5) 0.017(4) 0.015(3) -0.009(3) -0.005(3) 0.003(4) C60 0.015(3) 0.014(3) 0.017(2) -0.001(2) 0.001(2) -0.004(2) C61 0.020(5) 0.020(5) 0.011(3) -0.006(3) 0.002(3) 0.009(4) C62 0.019(3) 0.020(3) 0.021(3) 0.001(2) 0.000(2) 0.007(3) N11 0.030(4) 0.016(4) 0.017(3) -0.006(3) -0.013(3) 0.000(3) O11 0.037(4) 0.019(3) 0.024(3) -0.002(2) -0.008(2) -0.006(3) O12 0.039(3) 0.016(3) 0.033(3) 0.002(2) -0.010(3) 0.006(3) C63 0.027(5) 0.014(4) 0.026(4) -0.001(3) -0.012(4) 0.005(4) C64 0.015(5) 0.022(5) 0.026(4) 0.011(3) -0.011(4) -0.002(4) O13 0.024(4) 0.034(4) 0.037(3) 0.002(2) 0.000(3) 0.012(3) N12 0.037(4) 0.021(4) 0.027(3) 0.003(3) -0.001(3) 0.014(3) C65 0.058(6) 0.026(5) 0.023(4) 0.005(3) -0.004(4) 0.004(5) C66 0.045(6) 0.037(5) 0.039(5) -0.001(4) 0.010(4) 0.006(5) C67 0.084(7) 0.043(5) 0.040(5) 0.001(4) 0.006(5) 0.012(6) C68 0.052(7) 0.041(6) 0.087(7) -0.017(5) -0.009(6) 0.000(5) C69 0.071(8) 0.037(6) 0.032(5) -0.008(4) -0.032(5) 0.017(6) O14 0.076(5) 0.044(4) 0.036(3) 0.001(3) -0.006(3) 0.016(4) O15 0.075(5) 0.055(4) 0.032(3) 0.012(3) 0.001(3) -0.001(4) C70 0.104(9) 0.073(7) 0.038(5) 0.010(5) -0.016(6) 0.010(7) C71 0.082(8) 0.091(8) 0.057(6) 0.016(6) 0.029(6) -0.008(7) C72 0.012(4) 0.010(4) 0.021(4) 0.001(3) 0.000(3) -0.002(4) C73 0.016(4) 0.016(4) 0.011(3) -0.001(3) 0.000(3) 0.001(4) C74 0.020(5) 0.030(5) 0.024(4) 0.003(4) 0.008(4) -0.001(4) C75 0.006(4) 0.019(4) 0.018(3) 0.000(3) 0.002(3) 0.001(4) C76 0.015(3) 0.012(3) 0.018(2) -0.003(2) 0.002(2) 0.002(2) C77 0.013(4) 0.019(4) 0.024(4) -0.007(3) 0.004(3) 0.004(4) C78 0.012(4) 0.009(4) 0.025(4) 0.003(3) 0.005(4) -0.002(4) C79 0.013(4) 0.019(5) 0.028(4) 0.011(3) 0.000(3) 0.000(4) C80 0.018(5) 0.020(5) 0.015(3) 0.001(3) 0.003(3) -0.006(4) C81 0.014(4) 0.024(5) 0.014(3) 0.000(3) 0.001(3) -0.011(4) C82 0.021(3) 0.027(3) 0.029(3) 0.000(2) 0.002(2) -0.003(3) C83 0.009(5) 0.029(5) 0.031(5) 0.000(4) -0.001(4) 0.003(4) N13 0.019(4) 0.026(4) 0.014(3) -0.004(3) -0.009(3) -0.004(3) O16 0.059(4) 0.028(3) 0.032(3) -0.006(3) -0.019(3) -0.002(3) O17 0.029(3) 0.036(3) 0.029(3) -0.001(3) -0.006(3) 0.006(3) C84 0.039(5) 0.032(5) 0.025(4) -0.001(4) -0.005(4) -0.012(4) C85 0.037(6) 0.020(5) 0.022(4) -0.006(3) -0.013(4) 0.004(5) O18 0.031(4) 0.062(4) 0.032(3) 0.005(3) -0.004(3) -0.009(3) N14 0.026(4) 0.038(4) 0.029(3) 0.009(3) -0.005(3) -0.007(3) C86 0.035(5) 0.045(5) 0.021(4) -0.001(4) 0.002(4) -0.001(5) C87 0.036(5) 0.041(5) 0.033(4) -0.001(4) 0.004(4) 0.001(5) C88 0.088(8) 0.043(6) 0.055(6) -0.015(5) -0.018(6) -0.007(6) C89 0.067(7) 0.032(5) 0.076(6) 0.003(5) 0.003(6) -0.001(5) C90 0.029(6) 0.055(6) 0.033(5) 0.006(4) -0.003(5) -0.007(5) O19 0.034(4) 0.070(4) 0.031(3) -0.009(3) -0.009(3) -0.014(4) O20 0.038(4) 0.076(4) 0.028(3) -0.012(3) 0.004(3) -0.019(3) C91 0.069(7) 0.091(7) 0.029(5) -0.014(5) -0.014(5) -0.027(6) C92 0.071(7) 0.081(7) 0.038(5) -0.023(5) 0.010(5) 0.002(6) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C3 1.725(7) . ? Cl2 C5 1.730(7) . ? Cl3 C24 1.718(7) . ? Cl4 C26 1.728(6) . ? C1 C3 1.367(9) . ? C1 C4 1.429(9) . ? C1 C23 1.458(9) . ? C2 C5 1.388(8) . ? C2 C4 1.423(9) . ? C2 C22 1.476(8) . ? C3 C6 1.404(9) . ? C4 C7 1.410(9) . ? C5 C8 1.411(9) . ? C6 C9 1.374(9) . ? C7 C9 1.411(9) . ? C7 C10 1.412(9) . ? C8 C10 1.338(9) . ? C9 C11 1.493(9) . ? C10 C12 1.494(9) . ? C11 O1 1.201(8) . ? C11 N1 1.413(8) . ? C12 O2 1.201(8) . ? C12 N1 1.384(9) . ? N1 C13 1.469(8) . ? C13 C14 1.538(10) . ? C14 O3 1.200(8) . ? C14 N2 1.340(8) . ? N2 C15 1.461(9) . ? C15 C19 1.527(11) . ? C15 C16 1.542(10) . ? C16 C18 1.542(11) . ? C16 C17 1.545(12) . ? C19 O4 1.210(10) . ? C19 O5 1.321(10) . ? O5 C20 1.483(10) . ? C20 C21 1.477(13) . ? C22 C24 1.393(8) . ? C22 C25 1.424(9) . ? C23 C26 1.379(9) . ? C23 C25 1.436(9) . ? C24 C27 1.409(8) . ? C25 C28 1.399(9) . ? C26 C29 1.412(9) . ? C27 C30 1.380(9) . ? C28 C31 1.415(9) . ? C28 C30 1.432(8) . ? C29 C31 1.332(8) . ? C30 C32 1.458(9) . ? C31 C33 1.476(9) . ? C32 O6 1.221(7) . ? C32 N3 1.391(9) . ? C33 O7 1.239(8) . ? C33 N3 1.387(8) . ? N3 C34 1.439(8) . ? C34 C35 1.525(10) . ? C35 O8 1.211(10) . ? C35 N4 1.371(10) . ? N4 C36 1.460(9) . ? C36 C40 1.531(13) . ? C36 C37 1.552(12) . ? C37 C38 1.506(13) . ? C37 C39 1.540(11) . ? C40 O9 1.184(11) . ? C40 O10 1.340(10) . ? O10 C41 1.506(10) . ? C41 C42 1.477(12) . ? Cl5 C53 1.733(6) . ? Cl6 C55 1.732(7) . ? Cl7 C74 1.726(7) . ? Cl8 C76 1.727(7) . ? C51 C53 1.397(9) . ? C51 C54 1.434(9) . ? C51 C73 1.469(9) . ? C52 C55 1.391(9) . ? C52 C54 1.430(9) . ? C52 C72 1.473(8) . ? C53 C56 1.380(9) . ? C54 C57 1.410(9) . ? C55 C58 1.378(8) . ? C56 C59 1.396(9) . ? C57 C59 1.402(9) . ? C57 C60 1.409(9) . ? C58 C60 1.376(9) . ? C59 C61 1.470(9) . ? C60 C62 1.474(9) . ? C61 O11 1.198(8) . ? C61 N11 1.401(9) . ? C62 O12 1.208(8) . ? C62 N11 1.398(9) . ? N11 C63 1.451(8) . ? C63 C64 1.527(10) . ? C64 O13 1.187(8) . ? C64 N12 1.345(8) . ? N12 C65 1.447(8) . ? C65 C69 1.502(10) . ? C65 C66 1.534(10) . ? C66 C68 1.502(11) . ? C66 C67 1.516(10) . ? C69 O14 1.184(10) . ? C69 O15 1.353(10) . ? O15 C70 1.458(9) . ? C70 C71 1.564(12) . ? C72 C74 1.408(9) . ? C72 C75 1.423(9) . ? C73 C76 1.393(9) . ? C73 C75 1.414(8) . ? C74 C77 1.393(9) . ? C75 C78 1.415(9) . ? C76 C79 1.398(9) . ? C77 C80 1.362(9) . ? C78 C81 1.397(9) . ? C78 C80 1.400(9) . ? C79 C81 1.362(9) . ? C80 C82 1.455(9) . ? C81 C83 1.471(9) . ? C82 O16 1.225(8) . ? C82 N13 1.388(9) . ? C83 O17 1.217(8) . ? C83 N13 1.390(9) . ? N13 C84 1.444(8) . ? C84 C85 1.538(10) . ? C85 O18 1.204(9) . ? C85 N14 1.338(9) . ? N14 C86 1.440(8) . ? C86 C90 1.511(10) . ? C86 C87 1.520(10) . ? C87 C89 1.498(10) . ? C87 C88 1.528(10) . ? C90 O19 1.199(9) . ? C90 O20 1.320(9) . ? O20 C91 1.462(8) . ? C91 C92 1.492(11) . ? 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 C3 C1 C4 117.2(6) . . ? C3 C1 C23 125.6(6) . . ? C4 C1 C23 117.2(6) . . ? C5 C2 C4 116.3(5) . . ? C5 C2 C22 126.0(6) . . ? C4 C2 C22 117.5(5) . . ? C1 C3 C6 122.6(6) . . ? C1 C3 Cl1 122.9(5) . . ? C6 C3 Cl1 114.2(5) . . ? C7 C4 C2 119.2(6) . . ? C7 C4 C1 120.1(6) . . ? C2 C4 C1 120.7(6) . . ? C2 C5 C8 121.6(6) . . ? C2 C5 Cl2 122.6(5) . . ? C8 C5 Cl2 115.8(5) . . ? C9 C6 C3 119.6(7) . . ? C4 C7 C9 119.1(6) . . ? C4 C7 C10 120.2(6) . . ? C9 C7 C10 120.7(6) . . ? C10 C8 C5 121.0(6) . . ? C6 C9 C7 120.1(6) . . ? C6 C9 C11 119.4(6) . . ? C7 C9 C11 120.6(6) . . ? C8 C10 C7 119.2(6) . . ? C8 C10 C12 120.9(6) . . ? C7 C10 C12 119.8(6) . . ? O1 C11 N1 121.3(6) . . ? O1 C11 C9 122.8(6) . . ? N1 C11 C9 115.9(7) . . ? O2 C12 N1 120.4(6) . . ? O2 C12 C10 122.6(7) . . ? N1 C12 C10 116.9(6) . . ? C12 N1 C11 125.4(6) . . ? C12 N1 C13 117.4(6) . . ? C11 N1 C13 116.0(6) . . ? N1 C13 C14 107.7(6) . . ? O3 C14 N2 123.4(7) . . ? O3 C14 C13 121.8(6) . . ? N2 C14 C13 114.8(7) . . ? C14 N2 C15 127.4(6) . . ? N2 C15 C19 114.0(7) . . ? N2 C15 C16 111.7(6) . . ? C19 C15 C16 109.6(6) . . ? C18 C16 C15 112.7(7) . . ? C18 C16 C17 112.6(7) . . ? C15 C16 C17 109.6(7) . . ? O4 C19 O5 124.5(9) . . ? O4 C19 C15 122.6(8) . . ? O5 C19 C15 112.5(8) . . ? C19 O5 C20 116.3(7) . . ? C21 C20 O5 108.2(8) . . ? C24 C22 C25 117.0(6) . . ? C24 C22 C2 126.3(6) . . ? C25 C22 C2 116.6(5) . . ? C26 C23 C25 116.7(6) . . ? C26 C23 C1 126.1(6) . . ? C25 C23 C1 117.2(6) . . ? C22 C24 C27 121.1(6) . . ? C22 C24 Cl3 122.9(5) . . ? C27 C24 Cl3 115.8(5) . . ? C28 C25 C22 119.8(6) . . ? C28 C25 C23 119.3(6) . . ? C22 C25 C23 120.9(6) . . ? C23 C26 C29 122.2(6) . . ? C23 C26 Cl4 123.1(5) . . ? C29 C26 Cl4 114.5(5) . . ? C30 C27 C24 121.3(6) . . ? C25 C28 C31 119.1(6) . . ? C25 C28 C30 121.0(6) . . ? C31 C28 C30 119.9(6) . . ? C31 C29 C26 119.3(6) . . ? C27 C30 C28 117.3(6) . . ? C27 C30 C32 121.8(6) . . ? C28 C30 C32 120.8(6) . . ? C29 C31 C28 121.5(6) . . ? C29 C31 C33 119.5(6) . . ? C28 C31 C33 118.8(6) . . ? O6 C32 N3 120.5(6) . . ? O6 C32 C30 122.2(7) . . ? N3 C32 C30 117.3(6) . . ? O7 C33 N3 118.7(6) . . ? O7 C33 C31 122.4(6) . . ? N3 C33 C31 118.9(6) . . ? C33 N3 C32 123.9(6) . . ? C33 N3 C34 116.6(6) . . ? C32 N3 C34 119.3(6) . . ? N3 C34 C35 111.8(6) . . ? O8 C35 N4 126.9(8) . . ? O8 C35 C34 122.1(8) . . ? N4 C35 C34 110.9(8) . . ? C35 N4 C36 121.5(7) . . ? N4 C36 C40 107.4(7) . . ? N4 C36 C37 111.0(7) . . ? C40 C36 C37 110.9(7) . . ? C38 C37 C39 112.7(7) . . ? C38 C37 C36 114.0(8) . . ? C39 C37 C36 109.8(9) . . ? O9 C40 O10 123.3(10) . . ? O9 C40 C36 126.0(9) . . ? O10 C40 C36 110.7(10) . . ? C40 O10 C41 112.5(8) . . ? C42 C41 O10 113.7(7) . . ? C53 C51 C54 116.9(6) . . ? C53 C51 C73 126.6(6) . . ? C54 C51 C73 116.5(6) . . ? C55 C52 C54 116.1(5) . . ? C55 C52 C72 127.5(6) . . ? C54 C52 C72 116.5(5) . . ? C56 C53 C51 122.7(6) . . ? C56 C53 Cl5 115.4(5) . . ? C51 C53 Cl5 121.7(5) . . ? C57 C54 C52 119.6(6) . . ? C57 C54 C51 119.6(6) . . ? C52 C54 C51 120.8(6) . . ? C58 C55 C52 122.7(6) . . ? C58 C55 Cl6 115.8(5) . . ? C52 C55 Cl6 121.2(5) . . ? C53 C56 C59 119.6(6) . . ? C59 C57 C60 120.3(6) . . ? C59 C57 C54 120.2(6) . . ? C60 C57 C54 119.5(6) . . ? C60 C58 C55 120.0(6) . . ? C56 C59 C57 119.9(6) . . ? C56 C59 C61 118.4(6) . . ? C57 C59 C61 121.6(6) . . ? C58 C60 C57 119.4(6) . . ? C58 C60 C62 120.8(6) . . ? C57 C60 C62 119.7(6) . . ? O11 C61 N11 121.3(6) . . ? O11 C61 C59 123.3(6) . . ? N11 C61 C59 115.3(6) . . ? O12 C62 N11 120.1(6) . . ? O12 C62 C60 122.8(7) . . ? N11 C62 C60 117.0(6) . . ? C62 N11 C61 124.7(6) . . ? C62 N11 C63 118.5(6) . . ? C61 N11 C63 115.9(6) . . ? N11 C63 C64 109.9(6) . . ? O13 C64 N12 124.5(7) . . ? O13 C64 C63 122.6(7) . . ? N12 C64 C63 112.9(7) . . ? C64 N12 C65 121.7(7) . . ? N12 C65 C69 109.0(6) . . ? N12 C65 C66 113.0(6) . . ? C69 C65 C66 111.3(6) . . ? C68 C66 C67 112.1(7) . . ? C68 C66 C65 112.6(7) . . ? C67 C66 C65 109.7(6) . . ? O14 C69 O15 124.7(7) . . ? O14 C69 C65 127.0(9) . . ? O15 C69 C65 108.0(8) . . ? C69 O15 C70 115.5(7) . . ? O15 C70 C71 104.2(8) . . ? C74 C72 C75 116.4(6) . . ? C74 C72 C52 126.8(6) . . ? C75 C72 C52 116.8(6) . . ? C76 C73 C75 117.8(6) . . ? C76 C73 C51 125.2(6) . . ? C75 C73 C51 117.0(6) . . ? C77 C74 C72 121.4(6) . . ? C77 C74 Cl7 115.9(5) . . ? C72 C74 Cl7 122.5(5) . . ? C73 C75 C78 118.9(6) . . ? C73 C75 C72 121.2(6) . . ? C78 C75 C72 119.9(6) . . ? C73 C76 C79 120.7(6) . . ? C73 C76 Cl8 122.6(5) . . ? C79 C76 Cl8 116.6(5) . . ? C80 C77 C74 121.2(6) . . ? C81 C78 C80 119.9(6) . . ? C81 C78 C75 120.0(6) . . ? C80 C78 C75 120.1(6) . . ? C81 C79 C76 120.8(6) . . ? C77 C80 C78 119.3(6) . . ? C77 C80 C82 119.6(6) . . ? C78 C80 C82 121.1(7) . . ? C79 C81 C78 119.8(6) . . ? C79 C81 C83 119.7(7) . . ? C78 C81 C83 120.5(6) . . ? O16 C82 N13 120.2(7) . . ? O16 C82 C80 122.8(7) . . ? N13 C82 C80 116.9(6) . . ? O17 C83 N13 120.3(6) . . ? O17 C83 C81 122.8(7) . . ? N13 C83 C81 116.9(7) . . ? C82 N13 C83 124.5(6) . . ? C82 N13 C84 119.4(6) . . ? C83 N13 C84 115.8(6) . . ? N13 C84 C85 111.0(6) . . ? O18 C85 N14 126.2(7) . . ? O18 C85 C84 121.9(7) . . ? N14 C85 C84 111.9(7) . . ? C85 N14 C86 123.4(7) . . ? N14 C86 C90 106.8(6) . . ? N14 C86 C87 112.5(6) . . ? C90 C86 C87 110.8(6) . . ? C89 C87 C86 110.8(6) . . ? C89 C87 C88 110.5(7) . . ? C86 C87 C88 110.9(6) . . ? O19 C90 O20 124.6(7) . . ? O19 C90 C86 122.8(8) . . ? O20 C90 C86 112.5(7) . . ? C90 O20 C91 117.5(7) . . ? O20 C91 C92 105.6(7) . . ? 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 C1 C23 C26 -30.5(11) . . . . ? C5 C2 C22 C24 -36.2(11) . . . . ? C53 C51 C73 C76 31.9(10) . . . . ? C55 C52 C72 C74 31.2(11) . . . . ? _diffrn_measured_fraction_theta_max 0.776 _diffrn_reflns_theta_full 25.25 _diffrn_measured_fraction_theta_full 0.805 _refine_diff_density_max 0.408 _refine_diff_density_min -0.383 _refine_diff_density_rms 0.084