# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2008 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Chuan-Feng Chen' _publ_contact_author_email CCHEN@ICCAS.AC.CN _publ_section_title ; Triptycene-based tetralactam macrocycles: synthesis, structure and complexation with squaraine ; loop_ _publ_author_name 'Chuan-Feng Chen' 'Min Xue' # Attachment '1.cif' data_shelxl _database_code_depnum_ccdc_archive 'CCDC 697888' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C58 H40 Cl12 N6 O5' _chemical_formula_sum 'C58 H40 Cl12 N6 O5' _chemical_formula_weight 1326.36 _chemical_absolute_configuration ad 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 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 12.9178(12) _cell_length_b 21.121(2) _cell_length_c 21.125(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5763.6(10) _cell_formula_units_Z 4 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 10616 _cell_measurement_theta_min 1.8 _cell_measurement_theta_max 27.9 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.529 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2696 _exptl_absorpt_coefficient_mu 0.632 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9280 _exptl_absorpt_correction_T_max 0.9512 _exptl_absorpt_process_details crystalclear _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type 'Rigaku Saturn' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.31 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 51613 _diffrn_reflns_av_R_equivalents 0.1249 _diffrn_reflns_av_sigmaI/netI 0.1255 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.36 _diffrn_reflns_theta_max 27.10 _reflns_number_total 12695 _reflns_number_gt 9433 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'CrystalStructure 3.7.0' _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^)+(0.0556P)^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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0005(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.03(6) _refine_ls_number_reflns 12695 _refine_ls_number_parameters 743 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0948 _refine_ls_R_factor_gt 0.0672 _refine_ls_wR_factor_ref 0.1742 _refine_ls_wR_factor_gt 0.1574 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.084 _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 O1 O 0.5730(3) 0.28020(15) 0.27612(15) 0.0307(8) Uani 1 1 d . . . O2 O 0.5080(3) 0.60122(15) 0.35505(14) 0.0327(9) Uani 1 1 d . . . O3 O 0.6742(3) 0.47162(15) 0.89424(14) 0.0293(8) Uani 1 1 d . . . O4 O 0.7488(4) 0.15708(16) 0.80306(16) 0.0430(11) Uani 1 1 d . . . N1 N 0.6355(3) 0.32521(17) 0.36777(17) 0.0217(9) Uani 1 1 d D . . H1A H 0.652(4) 0.3615(12) 0.383(2) 0.026 Uiso 1 1 d D . . N2 N 0.5494(3) 0.43638(17) 0.33737(16) 0.0197(8) Uani 1 1 d . . . N3 N 0.5552(3) 0.52607(18) 0.42683(17) 0.0234(9) Uani 1 1 d D . . H3A H 0.559(4) 0.4861(7) 0.435(2) 0.028 Uiso 1 1 d D . . N4 N 0.7411(3) 0.44574(18) 0.79762(17) 0.0242(9) Uani 1 1 d D . . H4A H 0.771(4) 0.4162(17) 0.777(2) 0.029 Uiso 1 1 d D . . N5 N 0.7452(3) 0.32232(18) 0.82876(17) 0.0227(8) Uani 1 1 d . . . N6 N 0.8052(3) 0.23530(18) 0.73832(17) 0.0238(9) Uani 1 1 d D . . H6A H 0.831(4) 0.2729(11) 0.741(2) 0.029 Uiso 1 1 d D . . C1 C 0.8414(4) 0.1225(2) 0.4938(2) 0.0223(10) Uani 1 1 d . . . H1 H 0.8148 0.0784 0.4879 0.027 Uiso 1 1 calc R . . C2 C 0.7801(4) 0.1713(2) 0.4569(2) 0.0201(9) Uani 1 1 d . . . C3 C 0.6935(4) 0.1612(2) 0.4200(2) 0.0213(9) Uani 1 1 d . . . H3 H 0.6669 0.1195 0.4153 0.026 Uiso 1 1 calc R . . C4 C 0.6448(4) 0.2116(2) 0.38972(19) 0.0232(10) Uani 1 1 d . . . H4 H 0.5848 0.2044 0.3647 0.028 Uiso 1 1 calc R . . C5 C 0.6842(4) 0.2728(2) 0.39611(19) 0.0202(10) Uani 1 1 d . . . C6 C 0.7718(4) 0.2832(2) 0.43378(19) 0.0222(10) Uani 1 1 d . . . H6 H 0.7998 0.3246 0.4380 0.027 Uiso 1 1 calc R . . C7 C 0.8172(4) 0.2327(2) 0.46467(19) 0.0198(9) Uani 1 1 d . . . C8 C 0.9100(4) 0.2361(2) 0.5097(2) 0.0207(9) Uani 1 1 d . . . H8 H 0.9361 0.2803 0.5158 0.025 Uiso 1 1 calc R . . C9 C 0.8708(4) 0.2060(2) 0.5715(2) 0.0220(10) Uani 1 1 d . . . C10 C 0.8627(4) 0.2357(2) 0.62971(19) 0.0197(9) Uani 1 1 d . . . H10 H 0.8869 0.2778 0.6354 0.024 Uiso 1 1 calc R . . C11 C 0.8179(4) 0.2025(2) 0.6801(2) 0.0224(10) Uani 1 1 d . . . C12 C 0.7835(4) 0.1400(2) 0.6713(2) 0.0234(10) Uani 1 1 d . . . H12 H 0.7541 0.1172 0.7057 0.028 Uiso 1 1 calc R . . C13 C 0.7926(4) 0.1116(2) 0.6119(2) 0.0216(9) Uani 1 1 d . . . H13 H 0.7694 0.0694 0.6055 0.026 Uiso 1 1 calc R . . C14 C 0.8353(4) 0.1451(2) 0.5628(2) 0.0213(10) Uani 1 1 d . . . C15 C 0.9527(4) 0.1300(2) 0.47339(19) 0.0203(9) Uani 1 1 d . . . C16 C 1.0166(4) 0.0847(2) 0.4458(2) 0.0234(10) Uani 1 1 d . . . H16 H 0.9928 0.0424 0.4407 0.028 Uiso 1 1 calc R . . C17 C 1.1150(4) 0.1013(2) 0.4258(2) 0.0284(11) Uani 1 1 d . . . H17 H 1.1587 0.0704 0.4071 0.034 Uiso 1 1 calc R . . C18 C 1.1504(4) 0.1632(2) 0.4330(2) 0.0275(11) Uani 1 1 d . . . H18 H 1.2176 0.1744 0.4185 0.033 Uiso 1 1 calc R . . C19 C 1.0885(4) 0.2084(2) 0.4612(2) 0.0242(10) Uani 1 1 d . . . H19 H 1.1133 0.2504 0.4665 0.029 Uiso 1 1 calc R . . C20 C 0.9908(4) 0.1925(2) 0.4814(2) 0.0197(9) Uani 1 1 d . . . C21 C 0.5841(4) 0.3258(2) 0.3112(2) 0.0229(10) Uani 1 1 d . . . C22 C 0.5402(4) 0.3895(2) 0.2951(2) 0.0208(9) Uani 1 1 d . . . C23 C 0.4914(4) 0.3967(2) 0.2364(2) 0.0248(10) Uani 1 1 d . . . H23 H 0.4872 0.3625 0.2073 0.030 Uiso 1 1 calc R . . C24 C 0.4492(4) 0.4555(2) 0.2222(2) 0.0252(10) Uani 1 1 d . . . H24 H 0.4136 0.4617 0.1834 0.030 Uiso 1 1 calc R . . C25 C 0.4592(4) 0.5047(2) 0.2645(2) 0.0260(10) Uani 1 1 d . . . H25 H 0.4324 0.5455 0.2551 0.031 Uiso 1 1 calc R . . C26 C 0.5098(4) 0.4927(2) 0.3215(2) 0.0223(10) Uani 1 1 d . . . C27 C 0.5234(4) 0.5455(2) 0.3701(2) 0.0224(10) Uani 1 1 d . . . C28 C 0.7087(4) 0.6638(2) 0.6399(2) 0.0267(11) Uani 1 1 d . . . H28 H 0.6699 0.7016 0.6558 0.032 Uiso 1 1 calc R . . C29 C 0.6580(4) 0.6340(2) 0.5814(2) 0.0272(11) Uani 1 1 d . . . C30 C 0.5709(4) 0.6537(2) 0.5491(2) 0.0281(11) Uani 1 1 d . . . H30 H 0.5347 0.6905 0.5624 0.034 Uiso 1 1 calc R . . C31 C 0.5361(4) 0.6192(2) 0.4968(2) 0.0277(11) Uani 1 1 d . . . H31 H 0.4768 0.6330 0.4740 0.033 Uiso 1 1 calc R . . C32 C 0.5882(4) 0.5647(2) 0.4780(2) 0.0234(10) Uani 1 1 d . . . C33 C 0.6771(4) 0.5453(2) 0.5102(2) 0.0208(9) Uani 1 1 d . . . H33 H 0.7131 0.5083 0.4973 0.025 Uiso 1 1 calc R . . C34 C 0.7123(4) 0.5803(2) 0.5609(2) 0.0224(10) Uani 1 1 d . . . C35 C 0.8095(4) 0.5660(2) 0.5995(2) 0.0226(10) Uani 1 1 d . . . H35 H 0.8487 0.5283 0.5839 0.027 Uiso 1 1 calc R . . C36 C 0.7699(4) 0.5585(2) 0.6668(2) 0.0222(10) Uani 1 1 d . . . C37 C 0.7785(4) 0.5047(2) 0.70317(19) 0.0190(9) Uani 1 1 d . . . H37 H 0.8138 0.4686 0.6872 0.023 Uiso 1 1 calc R . . C38 C 0.7347(4) 0.5035(2) 0.7641(2) 0.0214(10) Uani 1 1 d . . . C39 C 0.6847(4) 0.5571(2) 0.7867(2) 0.0255(11) Uani 1 1 d . . . H39 H 0.6566 0.5569 0.8282 0.031 Uiso 1 1 calc R . . C40 C 0.6749(4) 0.6111(2) 0.7492(2) 0.0268(11) Uani 1 1 d . . . H40 H 0.6409 0.6477 0.7652 0.032 Uiso 1 1 calc R . . C41 C 0.7152(4) 0.6109(2) 0.6888(2) 0.0247(10) Uani 1 1 d . . . C42 C 0.8190(4) 0.6795(2) 0.6216(2) 0.0275(11) Uani 1 1 d . . . C43 C 0.8691(5) 0.7381(2) 0.6260(2) 0.0366(14) Uani 1 1 d . . . H43 H 0.8340 0.7738 0.6429 0.044 Uiso 1 1 calc R . . C44 C 0.9703(5) 0.7434(3) 0.6052(2) 0.0381(14) Uani 1 1 d . . . H44 H 1.0048 0.7831 0.6080 0.046 Uiso 1 1 calc R . . C45 C 1.0218(5) 0.6918(3) 0.5807(2) 0.0420(15) Uani 1 1 d . . . H45 H 1.0910 0.6964 0.5661 0.050 Uiso 1 1 calc R . . C46 C 0.9730(4) 0.6327(3) 0.5771(2) 0.0329(12) Uani 1 1 d . . . H46 H 1.0085 0.5971 0.5603 0.040 Uiso 1 1 calc R . . C47 C 0.8728(4) 0.6271(2) 0.59832(19) 0.0222(10) Uani 1 1 d . . . C48 C 0.7086(4) 0.4321(2) 0.85681(19) 0.0230(10) Uani 1 1 d . . . C49 C 0.7129(4) 0.3637(2) 0.8739(2) 0.0233(10) Uani 1 1 d . . . C50 C 0.6797(4) 0.3441(2) 0.9335(2) 0.0260(11) Uani 1 1 d . . . H50 H 0.6576 0.3743 0.9639 0.031 Uiso 1 1 calc R . . C51 C 0.6791(4) 0.2812(2) 0.9478(2) 0.0279(11) Uani 1 1 d . . . H51 H 0.6592 0.2673 0.9888 0.033 Uiso 1 1 calc R . . C52 C 0.7078(4) 0.2376(2) 0.9019(2) 0.0274(11) Uani 1 1 d . . . H52 H 0.7048 0.1934 0.9099 0.033 Uiso 1 1 calc R . . C53 C 0.7414(4) 0.2609(2) 0.8436(2) 0.0230(10) Uani 1 1 d . . . C54 C 0.7670(4) 0.2127(2) 0.7929(2) 0.0245(10) Uani 1 1 d . . . Cl1 Cl 0.53880(13) 0.36223(7) 0.73559(7) 0.0484(4) Uani 1 1 d . . . Cl2 Cl 0.34693(12) 0.29224(7) 0.72060(6) 0.0395(3) Uani 1 1 d . . . Cl3 Cl 0.54319(14) 0.23010(8) 0.70137(9) 0.0584(5) Uani 1 1 d . . . C55 C 0.4763(5) 0.3013(3) 0.6943(3) 0.0372(13) Uani 1 1 d . . . H55 H 0.4746 0.3131 0.6485 0.045 Uiso 1 1 calc R . . Cl4 Cl 1.01851(13) 0.38453(7) 0.42001(7) 0.0462(4) Uani 1 1 d . . . Cl5 Cl 0.90278(16) 0.41444(7) 0.53227(9) 0.0641(5) Uani 1 1 d . . . Cl6 Cl 1.09177(14) 0.48236(7) 0.50528(8) 0.0507(4) Uani 1 1 d . . . C56 C 0.9823(5) 0.4456(3) 0.4721(3) 0.0403(14) Uani 1 1 d . . . H56 H 0.9420 0.4780 0.4480 0.048 Uiso 1 1 calc R . . Cl7 Cl 0.30081(13) 0.45473(7) 0.67413(7) 0.0449(4) Uani 1 1 d . . . Cl8 Cl 0.30694(14) 0.55095(7) 0.57738(7) 0.0494(4) Uani 1 1 d . . . Cl9 Cl 0.46624(14) 0.54729(8) 0.67374(8) 0.0511(4) Uani 1 1 d . . . C57 C 0.3348(5) 0.5333(2) 0.6577(3) 0.0378(13) Uani 1 1 d . . . H57 H 0.2924 0.5618 0.6852 0.045 Uiso 1 1 calc R . . Cl10 Cl 0.77425(19) 0.91543(13) 0.6212(2) 0.1534(17) Uani 1 1 d . . . Cl11 Cl 0.5832(2) 0.85783(12) 0.59051(13) 0.0975(8) Uani 1 1 d . . . Cl12 Cl 0.5877(2) 0.97591(10) 0.66041(9) 0.0788(6) Uani 1 1 d . . . C58 C 0.6507(7) 0.9029(4) 0.6441(4) 0.071(2) Uani 1 1 d . . . H58 H 0.6533 0.8786 0.6847 0.086 Uiso 1 1 calc R . . O5 O 0.9611(4) 0.33854(18) 0.73753(18) 0.0507(12) Uani 1 1 d D . . H5A H 0.9702 0.3570 0.7729 0.076 Uiso 1 1 d RD . . H5B H 0.9938 0.3039 0.7334 0.076 Uiso 1 1 d RD . . 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 O1 0.045(3) 0.0234(17) 0.0239(16) -0.0024(14) -0.0026(16) -0.0002(16) O2 0.054(3) 0.0236(17) 0.0203(16) -0.0009(13) -0.0062(16) 0.0076(17) O3 0.037(2) 0.0294(18) 0.0214(15) -0.0006(13) 0.0029(15) 0.0085(16) O4 0.072(3) 0.0253(19) 0.0318(19) 0.0033(15) 0.020(2) -0.0057(19) N1 0.024(2) 0.0179(18) 0.0233(19) -0.0040(15) -0.0094(17) 0.0034(17) N2 0.020(2) 0.0215(18) 0.0176(17) -0.0010(14) -0.0032(15) -0.0019(16) N3 0.032(3) 0.0224(19) 0.0161(17) 0.0033(15) -0.0090(17) -0.0015(18) N4 0.027(2) 0.023(2) 0.0232(19) 0.0008(15) 0.0042(17) 0.0031(18) N5 0.020(2) 0.027(2) 0.0216(19) -0.0009(16) 0.0011(16) 0.0026(17) N6 0.029(2) 0.0222(19) 0.0206(18) -0.0012(15) 0.0012(17) -0.0032(18) C1 0.024(3) 0.017(2) 0.025(2) -0.0050(17) -0.0003(19) 0.0005(19) C2 0.017(2) 0.023(2) 0.020(2) -0.0022(17) 0.0003(18) 0.0008(19) C3 0.022(3) 0.0155(19) 0.027(2) 0.0044(17) 0.004(2) -0.0043(19) C4 0.023(3) 0.030(2) 0.017(2) -0.0007(17) -0.0010(18) -0.004(2) C5 0.026(3) 0.022(2) 0.0131(19) -0.0001(16) 0.0037(18) 0.002(2) C6 0.026(3) 0.021(2) 0.020(2) -0.0022(17) 0.0004(19) -0.0022(19) C7 0.019(2) 0.022(2) 0.018(2) 0.0005(17) 0.0028(18) -0.0004(19) C8 0.020(2) 0.021(2) 0.021(2) 0.0022(17) 0.0004(18) -0.004(2) C9 0.017(2) 0.024(2) 0.026(2) 0.0004(18) -0.0025(19) 0.0003(19) C10 0.024(3) 0.016(2) 0.020(2) 0.0025(16) 0.0001(18) 0.0005(19) C11 0.018(2) 0.027(2) 0.022(2) -0.0032(18) -0.0024(18) 0.001(2) C12 0.022(3) 0.026(2) 0.022(2) 0.0001(18) -0.0001(19) 0.004(2) C13 0.018(2) 0.019(2) 0.028(2) 0.0021(17) -0.0037(19) -0.0026(19) C14 0.019(3) 0.023(2) 0.022(2) -0.0003(17) -0.0031(18) 0.0031(19) C15 0.022(3) 0.025(2) 0.0144(19) 0.0008(16) -0.0066(18) 0.002(2) C16 0.026(3) 0.023(2) 0.021(2) -0.0026(17) -0.0053(19) 0.004(2) C17 0.025(3) 0.036(3) 0.025(2) -0.001(2) 0.002(2) 0.007(2) C18 0.024(3) 0.032(3) 0.026(2) 0.0016(19) 0.004(2) 0.002(2) C19 0.022(3) 0.030(2) 0.021(2) 0.0007(18) -0.0042(19) 0.002(2) C20 0.017(2) 0.021(2) 0.021(2) -0.0025(17) -0.0037(18) -0.0008(19) C21 0.021(3) 0.026(2) 0.022(2) -0.0001(18) 0.0026(19) -0.001(2) C22 0.012(2) 0.029(2) 0.022(2) 0.0026(18) -0.0005(18) -0.001(2) C23 0.023(3) 0.026(2) 0.026(2) -0.0023(18) 0.004(2) -0.004(2) C24 0.019(3) 0.039(3) 0.017(2) 0.0020(19) -0.0095(18) -0.005(2) C25 0.024(3) 0.029(2) 0.025(2) 0.0066(19) 0.001(2) 0.001(2) C26 0.018(2) 0.033(2) 0.016(2) -0.0009(18) -0.0030(18) 0.000(2) C27 0.018(3) 0.025(2) 0.024(2) 0.0010(18) -0.0055(18) -0.002(2) C28 0.039(3) 0.017(2) 0.023(2) -0.0047(17) -0.004(2) 0.004(2) C29 0.036(3) 0.022(2) 0.024(2) -0.0008(18) -0.001(2) 0.002(2) C30 0.035(3) 0.017(2) 0.033(2) -0.0011(19) -0.004(2) 0.004(2) C31 0.035(3) 0.023(2) 0.025(2) -0.0009(19) -0.004(2) 0.008(2) C32 0.031(3) 0.022(2) 0.017(2) -0.0002(17) -0.0030(19) -0.006(2) C33 0.020(3) 0.019(2) 0.023(2) 0.0011(17) 0.0004(18) 0.0001(19) C34 0.025(3) 0.021(2) 0.022(2) -0.0010(17) 0.0011(19) -0.003(2) C35 0.026(3) 0.020(2) 0.023(2) -0.0007(17) 0.0020(19) 0.000(2) C36 0.021(3) 0.022(2) 0.023(2) 0.0029(18) -0.0032(19) -0.0064(19) C37 0.023(3) 0.0154(19) 0.019(2) 0.0002(16) -0.0015(18) -0.0053(19) C38 0.027(3) 0.019(2) 0.018(2) -0.0024(17) -0.0038(18) -0.0010(19) C39 0.032(3) 0.024(2) 0.021(2) -0.0004(17) 0.006(2) 0.003(2) C40 0.038(3) 0.017(2) 0.025(2) -0.0003(17) -0.006(2) 0.000(2) C41 0.031(3) 0.021(2) 0.022(2) 0.0001(17) -0.006(2) 0.003(2) C42 0.035(3) 0.028(2) 0.020(2) 0.0033(18) -0.008(2) -0.008(2) C43 0.063(4) 0.025(2) 0.022(2) 0.0022(19) -0.007(3) -0.009(3) C44 0.055(4) 0.037(3) 0.023(2) 0.005(2) -0.008(3) -0.018(3) C45 0.044(4) 0.055(3) 0.027(3) 0.016(2) -0.010(2) -0.031(3) C46 0.037(3) 0.044(3) 0.018(2) 0.003(2) -0.004(2) -0.008(3) C47 0.030(3) 0.024(2) 0.0127(19) 0.0026(17) -0.0028(18) -0.009(2) C48 0.020(3) 0.031(2) 0.018(2) 0.0015(18) -0.0053(18) -0.003(2) C49 0.023(3) 0.025(2) 0.021(2) -0.0020(18) -0.0018(19) -0.003(2) C50 0.026(3) 0.031(2) 0.022(2) -0.0018(19) 0.004(2) 0.000(2) C51 0.037(3) 0.033(3) 0.014(2) 0.0041(18) 0.0017(19) -0.004(2) C52 0.035(3) 0.024(2) 0.023(2) 0.0023(18) 0.007(2) 0.005(2) C53 0.018(2) 0.026(2) 0.025(2) 0.0010(18) 0.0006(19) 0.002(2) C54 0.029(3) 0.028(2) 0.017(2) 0.0018(18) 0.0011(19) 0.003(2) Cl1 0.0461(10) 0.0531(9) 0.0461(8) -0.0071(7) -0.0068(7) -0.0163(8) Cl2 0.0322(8) 0.0434(8) 0.0429(7) 0.0007(6) -0.0055(6) -0.0037(6) Cl3 0.0372(9) 0.0477(9) 0.0901(12) 0.0011(8) 0.0020(9) 0.0046(8) C55 0.036(3) 0.035(3) 0.041(3) -0.003(2) -0.003(3) -0.003(3) Cl4 0.0426(9) 0.0389(7) 0.0571(9) -0.0006(7) 0.0067(7) -0.0022(7) Cl5 0.0721(14) 0.0339(8) 0.0862(12) -0.0107(8) 0.0332(11) -0.0043(8) Cl6 0.0453(10) 0.0367(7) 0.0701(10) 0.0017(7) -0.0188(8) -0.0023(7) C56 0.039(4) 0.035(3) 0.047(3) 0.001(2) -0.001(3) -0.003(3) Cl7 0.0434(9) 0.0339(7) 0.0574(8) -0.0092(6) 0.0014(7) -0.0052(6) Cl8 0.0596(11) 0.0386(7) 0.0501(8) -0.0084(6) -0.0141(8) 0.0039(7) Cl9 0.0432(10) 0.0506(9) 0.0596(9) -0.0030(7) -0.0110(8) -0.0110(8) C57 0.036(4) 0.025(3) 0.052(3) -0.013(2) 0.002(3) 0.001(2) Cl10 0.0414(13) 0.0809(17) 0.338(5) -0.067(2) -0.008(2) -0.0035(12) Cl11 0.0806(18) 0.0989(17) 0.1131(17) -0.0040(14) -0.0356(14) -0.0325(14) Cl12 0.0847(17) 0.0866(14) 0.0652(11) 0.0268(10) 0.0095(11) 0.0237(12) C58 0.055(5) 0.070(5) 0.089(6) 0.024(4) -0.013(4) -0.005(4) O5 0.069(3) 0.040(2) 0.043(2) -0.0122(18) -0.006(2) -0.017(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C21 1.223(5) . ? O2 C27 1.236(5) . ? O3 C48 1.232(5) . ? O4 C54 1.218(6) . ? N1 C21 1.368(6) . ? N1 C5 1.408(6) . ? N1 H1A 0.860(10) . ? N2 C26 1.337(6) . ? N2 C22 1.339(5) . ? N3 C27 1.331(5) . ? N3 C32 1.420(6) . ? N3 H3A 0.861(10) . ? N4 C48 1.350(5) . ? N4 C38 1.414(6) . ? N4 H4A 0.859(10) . ? N5 C53 1.335(6) . ? N5 C49 1.361(6) . ? N6 C54 1.341(6) . ? N6 C11 1.422(6) . ? N6 H6A 0.861(10) . ? C1 C15 1.509(7) . ? C1 C2 1.515(6) . ? C1 C14 1.537(6) . ? C1 H1 1.0000 . ? C2 C3 1.380(6) . ? C2 C7 1.393(6) . ? C3 C4 1.393(6) . ? C3 H3 0.9500 . ? C4 C5 1.395(6) . ? C4 H4 0.9500 . ? C5 C6 1.401(6) . ? C6 C7 1.380(6) . ? C6 H6 0.9500 . ? C7 C8 1.533(6) . ? C8 C20 1.515(6) . ? C8 C9 1.538(6) . ? C8 H8 1.0000 . ? C9 C14 1.378(6) . ? C9 C10 1.385(6) . ? C10 C11 1.400(6) . ? C10 H10 0.9500 . ? C11 C12 1.403(6) . ? C12 C13 1.397(6) . ? C12 H12 0.9500 . ? C13 C14 1.371(6) . ? C13 H13 0.9500 . ? C15 C16 1.392(6) . ? C15 C20 1.419(6) . ? C16 C17 1.385(7) . ? C16 H16 0.9500 . ? C17 C18 1.394(7) . ? C17 H17 0.9500 . ? C18 C19 1.380(7) . ? C18 H18 0.9500 . ? C19 C20 1.374(7) . ? C19 H19 0.9500 . ? C21 C22 1.499(6) . ? C22 C23 1.399(6) . ? C23 C24 1.388(7) . ? C23 H23 0.9500 . ? C24 C25 1.377(6) . ? C24 H24 0.9500 . ? C25 C26 1.394(6) . ? C25 H25 0.9500 . ? C26 C27 1.525(6) . ? C28 C42 1.513(8) . ? C28 C41 1.525(6) . ? C28 C29 1.533(6) . ? C28 H28 1.0000 . ? C29 C30 1.380(7) . ? C29 C34 1.403(7) . ? C30 C31 1.398(6) . ? C30 H30 0.9500 . ? C31 C32 1.393(7) . ? C31 H31 0.9500 . ? C32 C33 1.395(7) . ? C33 C34 1.376(6) . ? C33 H33 0.9500 . ? C34 C35 1.529(7) . ? C35 C36 1.520(6) . ? C35 C47 1.528(6) . ? C35 H35 1.0000 . ? C36 C37 1.375(6) . ? C36 C41 1.393(6) . ? C37 C38 1.405(6) . ? C37 H37 0.9500 . ? C38 C39 1.387(6) . ? C39 C40 1.395(6) . ? C39 H39 0.9500 . ? C40 C41 1.378(6) . ? C40 H40 0.9500 . ? C42 C47 1.394(7) . ? C42 C43 1.401(7) . ? C43 C44 1.384(9) . ? C43 H43 0.9500 . ? C44 C45 1.378(9) . ? C44 H44 0.9500 . ? C45 C46 1.401(7) . ? C45 H45 0.9500 . ? C46 C47 1.375(7) . ? C46 H46 0.9500 . ? C48 C49 1.489(6) . ? C49 C50 1.392(6) . ? C50 C51 1.362(6) . ? C50 H50 0.9500 . ? C51 C52 1.388(6) . ? C51 H51 0.9500 . ? C52 C53 1.395(6) . ? C52 H52 0.9500 . ? C53 C54 1.514(6) . ? Cl1 C55 1.751(5) . ? Cl2 C55 1.772(6) . ? Cl3 C55 1.740(6) . ? C55 H55 1.0000 . ? Cl4 C56 1.759(6) . ? Cl5 C56 1.761(6) . ? Cl6 C56 1.759(6) . ? C56 H56 1.0000 . ? Cl7 C57 1.751(5) . ? Cl8 C57 1.775(6) . ? Cl9 C57 1.756(6) . ? C57 H57 1.0000 . ? Cl10 C58 1.688(9) . ? Cl11 C58 1.718(8) . ? Cl12 C58 1.777(8) . ? C58 H58 1.0000 . ? O5 H5A 0.8507 . ? O5 H5B 0.8501 . ? 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 C21 N1 C5 126.6(4) . . ? C21 N1 H1A 117(3) . . ? C5 N1 H1A 115(3) . . ? C26 N2 C22 117.2(4) . . ? C27 N3 C32 127.0(4) . . ? C27 N3 H3A 119(3) . . ? C32 N3 H3A 114(3) . . ? C48 N4 C38 129.1(4) . . ? C48 N4 H4A 118(3) . . ? C38 N4 H4A 113(3) . . ? C53 N5 C49 116.7(4) . . ? C54 N6 C11 127.8(4) . . ? C54 N6 H6A 115(3) . . ? C11 N6 H6A 117(3) . . ? C15 C1 C2 106.2(4) . . ? C15 C1 C14 106.7(4) . . ? C2 C1 C14 104.5(3) . . ? C15 C1 H1 112.9 . . ? C2 C1 H1 112.9 . . ? C14 C1 H1 112.9 . . ? C3 C2 C7 119.3(4) . . ? C3 C2 C1 127.5(4) . . ? C7 C2 C1 113.2(4) . . ? C2 C3 C4 120.5(4) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C3 C4 C5 119.9(4) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C4 C5 C6 119.7(4) . . ? C4 C5 N1 121.6(4) . . ? C6 C5 N1 118.6(4) . . ? C7 C6 C5 119.3(4) . . ? C7 C6 H6 120.3 . . ? C5 C6 H6 120.3 . . ? C6 C7 C2 121.2(4) . . ? C6 C7 C8 126.1(4) . . ? C2 C7 C8 112.7(4) . . ? C20 C8 C7 105.4(3) . . ? C20 C8 C9 108.1(4) . . ? C7 C8 C9 104.4(4) . . ? C20 C8 H8 112.8 . . ? C7 C8 H8 112.8 . . ? C9 C8 H8 112.8 . . ? C14 C9 C10 121.0(4) . . ? C14 C9 C8 112.5(4) . . ? C10 C9 C8 126.3(4) . . ? C9 C10 C11 118.7(4) . . ? C9 C10 H10 120.7 . . ? C11 C10 H10 120.7 . . ? C10 C11 C12 120.1(4) . . ? C10 C11 N6 117.4(4) . . ? C12 C11 N6 122.4(4) . . ? C13 C12 C11 119.8(4) . . ? C13 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? C14 C13 C12 119.4(4) . . ? C14 C13 H13 120.3 . . ? C12 C13 H13 120.3 . . ? C13 C14 C9 121.0(4) . . ? C13 C14 C1 125.3(4) . . ? C9 C14 C1 113.5(4) . . ? C16 C15 C20 119.0(5) . . ? C16 C15 C1 127.7(4) . . ? C20 C15 C1 113.2(4) . . ? C17 C16 C15 119.8(5) . . ? C17 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? C16 C17 C18 120.4(5) . . ? C16 C17 H17 119.8 . . ? C18 C17 H17 119.8 . . ? C19 C18 C17 120.4(5) . . ? C19 C18 H18 119.8 . . ? C17 C18 H18 119.8 . . ? C20 C19 C18 119.8(5) . . ? C20 C19 H19 120.1 . . ? C18 C19 H19 120.1 . . ? C19 C20 C15 120.6(4) . . ? C19 C20 C8 127.3(4) . . ? C15 C20 C8 112.0(4) . . ? O1 C21 N1 125.4(4) . . ? O1 C21 C22 121.7(4) . . ? N1 C21 C22 112.9(4) . . ? N2 C22 C23 123.4(4) . . ? N2 C22 C21 118.6(4) . . ? C23 C22 C21 118.0(4) . . ? C24 C23 C22 117.8(4) . . ? C24 C23 H23 121.1 . . ? C22 C23 H23 121.1 . . ? C25 C24 C23 119.9(4) . . ? C25 C24 H24 120.1 . . ? C23 C24 H24 120.1 . . ? C24 C25 C26 117.8(4) . . ? C24 C25 H25 121.1 . . ? C26 C25 H25 121.1 . . ? N2 C26 C25 123.9(4) . . ? N2 C26 C27 116.0(4) . . ? C25 C26 C27 120.2(4) . . ? O2 C27 N3 125.1(4) . . ? O2 C27 C26 120.3(4) . . ? N3 C27 C26 114.6(4) . . ? C42 C28 C41 106.3(4) . . ? C42 C28 C29 106.6(4) . . ? C41 C28 C29 105.6(4) . . ? C42 C28 H28 112.6 . . ? C41 C28 H28 112.6 . . ? C29 C28 H28 112.6 . . ? C30 C29 C34 119.8(4) . . ? C30 C29 C28 128.5(4) . . ? C34 C29 C28 111.6(4) . . ? C29 C30 C31 119.8(5) . . ? C29 C30 H30 120.1 . . ? C31 C30 H30 120.1 . . ? C32 C31 C30 120.0(5) . . ? C32 C31 H31 120.0 . . ? C30 C31 H31 120.0 . . ? C31 C32 C33 120.1(4) . . ? C31 C32 N3 123.1(5) . . ? C33 C32 N3 116.8(4) . . ? C34 C33 C32 119.6(4) . . ? C34 C33 H33 120.2 . . ? C32 C33 H33 120.2 . . ? C33 C34 C29 120.6(5) . . ? C33 C34 C35 125.5(4) . . ? C29 C34 C35 113.9(4) . . ? C36 C35 C47 106.5(3) . . ? C36 C35 C34 104.1(4) . . ? C47 C35 C34 105.3(4) . . ? C36 C35 H35 113.4 . . ? C47 C35 H35 113.4 . . ? C34 C35 H35 113.4 . . ? C37 C36 C41 120.8(4) . . ? C37 C36 C35 125.5(4) . . ? C41 C36 C35 113.6(4) . . ? C36 C37 C38 119.5(4) . . ? C36 C37 H37 120.2 . . ? C38 C37 H37 120.2 . . ? C39 C38 C37 119.2(4) . . ? C39 C38 N4 123.9(4) . . ? C37 C38 N4 116.8(4) . . ? C38 C39 C40 120.9(4) . . ? C38 C39 H39 119.5 . . ? C40 C39 H39 119.5 . . ? C41 C40 C39 119.3(4) . . ? C41 C40 H40 120.3 . . ? C39 C40 H40 120.3 . . ? C40 C41 C36 120.1(4) . . ? C40 C41 C28 127.3(4) . . ? C36 C41 C28 112.6(4) . . ? C47 C42 C43 119.7(5) . . ? C47 C42 C28 112.7(4) . . ? C43 C42 C28 127.6(5) . . ? C44 C43 C42 119.1(5) . . ? C44 C43 H43 120.4 . . ? C42 C43 H43 120.4 . . ? C45 C44 C43 120.7(5) . . ? C45 C44 H44 119.6 . . ? C43 C44 H44 119.6 . . ? C44 C45 C46 120.5(6) . . ? C44 C45 H45 119.7 . . ? C46 C45 H45 119.7 . . ? C47 C46 C45 118.9(6) . . ? C47 C46 H46 120.6 . . ? C45 C46 H46 120.6 . . ? C46 C47 C42 121.0(4) . . ? C46 C47 C35 125.5(5) . . ? C42 C47 C35 113.5(4) . . ? O3 C48 N4 124.2(4) . . ? O3 C48 C49 120.9(4) . . ? N4 C48 C49 114.8(4) . . ? N5 C49 C50 122.4(4) . . ? N5 C49 C48 117.7(4) . . ? C50 C49 C48 119.8(4) . . ? C51 C50 C49 119.6(4) . . ? C51 C50 H50 120.2 . . ? C49 C50 H50 120.2 . . ? C50 C51 C52 119.3(4) . . ? C50 C51 H51 120.4 . . ? C52 C51 H51 120.4 . . ? C51 C52 C53 117.8(4) . . ? C51 C52 H52 121.1 . . ? C53 C52 H52 121.1 . . ? N5 C53 C52 124.1(4) . . ? N5 C53 C54 118.6(4) . . ? C52 C53 C54 117.1(4) . . ? O4 C54 N6 124.5(4) . . ? O4 C54 C53 118.8(4) . . ? N6 C54 C53 116.7(4) . . ? Cl3 C55 Cl1 111.3(3) . . ? Cl3 C55 Cl2 110.4(3) . . ? Cl1 C55 Cl2 111.0(3) . . ? Cl3 C55 H55 108.0 . . ? Cl1 C55 H55 108.0 . . ? Cl2 C55 H55 108.0 . . ? Cl6 C56 Cl4 111.1(3) . . ? Cl6 C56 Cl5 110.3(3) . . ? Cl4 C56 Cl5 109.4(3) . . ? Cl6 C56 H56 108.7 . . ? Cl4 C56 H56 108.7 . . ? Cl5 C56 H56 108.7 . . ? Cl7 C57 Cl9 111.4(3) . . ? Cl7 C57 Cl8 109.7(3) . . ? Cl9 C57 Cl8 110.2(3) . . ? Cl7 C57 H57 108.5 . . ? Cl9 C57 H57 108.5 . . ? Cl8 C57 H57 108.5 . . ? Cl10 C58 Cl11 112.2(5) . . ? Cl10 C58 Cl12 110.7(4) . . ? Cl11 C58 Cl12 112.1(5) . . ? Cl10 C58 H58 107.2 . . ? Cl11 C58 H58 107.2 . . ? Cl12 C58 H58 107.2 . . ? H5A O5 H5B 114.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C15 C1 C2 C3 127.0(5) . . . . ? C14 C1 C2 C3 -120.5(5) . . . . ? C15 C1 C2 C7 -55.4(5) . . . . ? C14 C1 C2 C7 57.2(5) . . . . ? C7 C2 C3 C4 1.4(7) . . . . ? C1 C2 C3 C4 179.0(4) . . . . ? C2 C3 C4 C5 0.6(7) . . . . ? C3 C4 C5 C6 -0.9(6) . . . . ? C3 C4 C5 N1 -178.1(4) . . . . ? C21 N1 C5 C4 -34.1(7) . . . . ? C21 N1 C5 C6 148.7(5) . . . . ? C4 C5 C6 C7 -0.8(6) . . . . ? N1 C5 C6 C7 176.5(4) . . . . ? C5 C6 C7 C2 2.9(7) . . . . ? C5 C6 C7 C8 -177.3(4) . . . . ? C3 C2 C7 C6 -3.2(7) . . . . ? C1 C2 C7 C6 178.9(4) . . . . ? C3 C2 C7 C8 176.9(4) . . . . ? C1 C2 C7 C8 -1.0(5) . . . . ? C6 C7 C8 C20 -122.5(5) . . . . ? C2 C7 C8 C20 57.4(5) . . . . ? C6 C7 C8 C9 123.7(5) . . . . ? C2 C7 C8 C9 -56.4(5) . . . . ? C20 C8 C9 C14 -54.5(5) . . . . ? C7 C8 C9 C14 57.4(5) . . . . ? C20 C8 C9 C10 130.3(5) . . . . ? C7 C8 C9 C10 -117.9(5) . . . . ? C14 C9 C10 C11 0.3(7) . . . . ? C8 C9 C10 C11 175.2(4) . . . . ? C9 C10 C11 C12 0.8(7) . . . . ? C9 C10 C11 N6 -176.5(4) . . . . ? C54 N6 C11 C10 -178.1(5) . . . . ? C54 N6 C11 C12 4.7(8) . . . . ? C10 C11 C12 C13 -1.0(7) . . . . ? N6 C11 C12 C13 176.2(4) . . . . ? C11 C12 C13 C14 0.1(7) . . . . ? C12 C13 C14 C9 1.0(7) . . . . ? C12 C13 C14 C1 -174.1(5) . . . . ? C10 C9 C14 C13 -1.3(7) . . . . ? C8 C9 C14 C13 -176.8(4) . . . . ? C10 C9 C14 C1 174.4(4) . . . . ? C8 C9 C14 C1 -1.1(6) . . . . ? C15 C1 C14 C13 -128.6(5) . . . . ? C2 C1 C14 C13 119.2(5) . . . . ? C15 C1 C14 C9 55.9(5) . . . . ? C2 C1 C14 C9 -56.3(5) . . . . ? C2 C1 C15 C16 -121.0(5) . . . . ? C14 C1 C15 C16 127.9(4) . . . . ? C2 C1 C15 C20 55.4(4) . . . . ? C14 C1 C15 C20 -55.6(5) . . . . ? C20 C15 C16 C17 -0.9(6) . . . . ? C1 C15 C16 C17 175.3(4) . . . . ? C15 C16 C17 C18 -0.2(7) . . . . ? C16 C17 C18 C19 1.1(7) . . . . ? C17 C18 C19 C20 -0.9(7) . . . . ? C18 C19 C20 C15 -0.2(7) . . . . ? C18 C19 C20 C8 -176.4(4) . . . . ? C16 C15 C20 C19 1.2(6) . . . . ? C1 C15 C20 C19 -175.6(4) . . . . ? C16 C15 C20 C8 177.8(4) . . . . ? C1 C15 C20 C8 1.1(5) . . . . ? C7 C8 C20 C19 119.4(5) . . . . ? C9 C8 C20 C19 -129.3(5) . . . . ? C7 C8 C20 C15 -57.0(4) . . . . ? C9 C8 C20 C15 54.3(5) . . . . ? C5 N1 C21 O1 -0.4(8) . . . . ? C5 N1 C21 C22 179.4(4) . . . . ? C26 N2 C22 C23 -0.5(7) . . . . ? C26 N2 C22 C21 179.7(4) . . . . ? O1 C21 C22 N2 175.8(5) . . . . ? N1 C21 C22 N2 -4.0(6) . . . . ? O1 C21 C22 C23 -4.0(7) . . . . ? N1 C21 C22 C23 176.2(4) . . . . ? N2 C22 C23 C24 -0.9(7) . . . . ? C21 C22 C23 C24 178.9(4) . . . . ? C22 C23 C24 C25 2.0(7) . . . . ? C23 C24 C25 C26 -1.6(7) . . . . ? C22 N2 C26 C25 0.9(7) . . . . ? C22 N2 C26 C27 -178.8(4) . . . . ? C24 C25 C26 N2 0.2(7) . . . . ? C24 C25 C26 C27 179.8(5) . . . . ? C32 N3 C27 O2 -7.4(9) . . . . ? C32 N3 C27 C26 170.4(4) . . . . ? N2 C26 C27 O2 165.8(5) . . . . ? C25 C26 C27 O2 -13.9(7) . . . . ? N2 C26 C27 N3 -12.2(6) . . . . ? C25 C26 C27 N3 168.2(5) . . . . ? C42 C28 C29 C30 -122.1(6) . . . . ? C41 C28 C29 C30 125.1(5) . . . . ? C42 C28 C29 C34 57.5(5) . . . . ? C41 C28 C29 C34 -55.3(5) . . . . ? C34 C29 C30 C31 1.2(8) . . . . ? C28 C29 C30 C31 -179.2(5) . . . . ? C29 C30 C31 C32 1.1(7) . . . . ? C30 C31 C32 C33 -1.9(7) . . . . ? C30 C31 C32 N3 177.7(4) . . . . ? C27 N3 C32 C31 44.5(7) . . . . ? C27 N3 C32 C33 -135.9(5) . . . . ? C31 C32 C33 C34 0.5(7) . . . . ? N3 C32 C33 C34 -179.1(4) . . . . ? C32 C33 C34 C29 1.8(7) . . . . ? C32 C33 C34 C35 -178.3(4) . . . . ? C30 C29 C34 C33 -2.6(7) . . . . ? C28 C29 C34 C33 177.7(4) . . . . ? C30 C29 C34 C35 177.5(4) . . . . ? C28 C29 C34 C35 -2.2(6) . . . . ? C33 C34 C35 C36 -122.0(5) . . . . ? C29 C34 C35 C36 57.8(5) . . . . ? C33 C34 C35 C47 126.2(5) . . . . ? C29 C34 C35 C47 -54.0(5) . . . . ? C47 C35 C36 C37 -129.7(5) . . . . ? C34 C35 C36 C37 119.3(5) . . . . ? C47 C35 C36 C41 54.6(5) . . . . ? C34 C35 C36 C41 -56.3(5) . . . . ? C41 C36 C37 C38 -2.3(7) . . . . ? C35 C36 C37 C38 -177.6(4) . . . . ? C36 C37 C38 C39 -0.8(7) . . . . ? C36 C37 C38 N4 176.5(4) . . . . ? C48 N4 C38 C39 -5.0(8) . . . . ? C48 N4 C38 C37 177.9(5) . . . . ? C37 C38 C39 C40 1.7(8) . . . . ? N4 C38 C39 C40 -175.4(5) . . . . ? C38 C39 C40 C41 0.4(8) . . . . ? C39 C40 C41 C36 -3.5(7) . . . . ? C39 C40 C41 C28 177.3(5) . . . . ? C37 C36 C41 C40 4.5(7) . . . . ? C35 C36 C41 C40 -179.7(4) . . . . ? C37 C36 C41 C28 -176.2(4) . . . . ? C35 C36 C41 C28 -0.4(6) . . . . ? C42 C28 C41 C40 123.4(5) . . . . ? C29 C28 C41 C40 -123.5(5) . . . . ? C42 C28 C41 C36 -55.8(5) . . . . ? C29 C28 C41 C36 57.2(6) . . . . ? C41 C28 C42 C47 57.3(5) . . . . ? C29 C28 C42 C47 -55.0(5) . . . . ? C41 C28 C42 C43 -122.4(5) . . . . ? C29 C28 C42 C43 125.3(5) . . . . ? C47 C42 C43 C44 1.9(7) . . . . ? C28 C42 C43 C44 -178.4(4) . . . . ? C42 C43 C44 C45 -0.1(7) . . . . ? C43 C44 C45 C46 -1.0(8) . . . . ? C44 C45 C46 C47 0.2(7) . . . . ? C45 C46 C47 C42 1.6(7) . . . . ? C45 C46 C47 C35 -178.2(4) . . . . ? C43 C42 C47 C46 -2.7(7) . . . . ? C28 C42 C47 C46 177.6(4) . . . . ? C43 C42 C47 C35 177.1(4) . . . . ? C28 C42 C47 C35 -2.6(5) . . . . ? C36 C35 C47 C46 126.7(5) . . . . ? C34 C35 C47 C46 -123.2(5) . . . . ? C36 C35 C47 C42 -53.1(5) . . . . ? C34 C35 C47 C42 57.0(5) . . . . ? C38 N4 C48 O3 -6.5(8) . . . . ? C38 N4 C48 C49 171.1(5) . . . . ? C53 N5 C49 C50 1.6(7) . . . . ? C53 N5 C49 C48 -175.3(4) . . . . ? O3 C48 C49 N5 175.7(4) . . . . ? N4 C48 C49 N5 -2.0(6) . . . . ? O3 C48 C49 C50 -1.3(7) . . . . ? N4 C48 C49 C50 -179.0(5) . . . . ? N5 C49 C50 C51 0.0(8) . . . . ? C48 C49 C50 C51 176.8(5) . . . . ? C49 C50 C51 C52 -2.5(8) . . . . ? C50 C51 C52 C53 3.2(8) . . . . ? C49 N5 C53 C52 -0.8(7) . . . . ? C49 N5 C53 C54 174.4(4) . . . . ? C51 C52 C53 N5 -1.6(8) . . . . ? C51 C52 C53 C54 -176.9(5) . . . . ? C11 N6 C54 O4 9.6(9) . . . . ? C11 N6 C54 C53 -167.7(5) . . . . ? N5 C53 C54 O4 -169.1(5) . . . . ? C52 C53 C54 O4 6.4(7) . . . . ? N5 C53 C54 N6 8.4(7) . . . . ? C52 C53 C54 N6 -176.1(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 O5 H5B O1 0.85 2.06 2.909(5) 179.7 2_556 O5 H5A O2 0.85 1.97 2.818(5) 179.4 4_665 N6 H6A O5 0.861(10) 2.18(3) 2.968(6) 151(5) . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.10 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.553 _refine_diff_density_min -0.788 _refine_diff_density_rms 0.082 # Attachment '2-3.cif' data_shelxlb _database_code_depnum_ccdc_archive 'CCDC 697889' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C80 H64 Cl6 N8 O6' _chemical_formula_sum 'C80 H64 Cl6 N8 O6' _chemical_formula_weight 1446.09 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.589(3) _cell_length_b 13.760(4) _cell_length_c 24.086(8) _cell_angle_alpha 89.709(9) _cell_angle_beta 88.570(10) _cell_angle_gamma 78.582(8) _cell_volume 3438.9(19) _cell_formula_units_Z 2 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 7000 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 27.2 _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.397 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1500 _exptl_absorpt_coefficient_mu 0.313 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9401 _exptl_absorpt_correction_T_max 0.9876 _exptl_absorpt_process_details crystalclear _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type 'Rigaku Saturn CCD area detector' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.31 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 35589 _diffrn_reflns_av_R_equivalents 0.0631 _diffrn_reflns_av_sigmaI/netI 0.0748 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 25.00 _reflns_number_total 12114 _reflns_number_gt 8070 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku/MSC Inc.,2005)' _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'CrystalStructure 3.7.0' _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^)+(0.1168P)^2^+3.8415P] 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_number_reflns 12114 _refine_ls_number_parameters 950 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.1160 _refine_ls_R_factor_gt 0.0768 _refine_ls_wR_factor_ref 0.2346 _refine_ls_wR_factor_gt 0.1994 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.002 _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 N1 N 0.4340(3) 0.6935(2) 0.16920(14) 0.0273(7) Uani 1 1 d . . . H1 H 0.4736 0.6936 0.1352 0.041 Uiso 1 1 d R . . N2 N 0.5164(3) 0.8444(2) 0.11935(14) 0.0276(7) Uani 1 1 d . . . N3 N 0.5849(4) 0.8243(3) 0.01054(15) 0.0298(8) Uani 1 1 d . . . N7 N 0.4068(3) 0.5603(3) 0.40555(14) 0.0355(9) Uani 1 1 d . . . N8 N -0.0754(3) 0.4588(3) 0.10050(14) 0.0360(9) Uani 1 1 d . . . O1 O 0.3706(3) 0.7863(2) 0.24660(12) 0.0361(7) Uani 1 1 d . . . O2 O 0.6735(3) 0.9629(2) 0.01506(13) 0.0423(8) Uani 1 1 d . . . O6 O 0.4979(3) 0.6367(2) 0.05267(11) 0.0309(6) Uani 1 1 d . . . C1 C 0.4182(4) 0.7767(3) 0.19984(17) 0.0276(9) Uani 1 1 d . . . C2 C 0.4709(4) 0.8592(3) 0.17200(17) 0.0263(9) Uani 1 1 d . . . C3 C 0.4721(4) 0.9451(3) 0.20163(18) 0.0330(10) Uani 1 1 d . . . H3 H 0.4375 0.9533 0.2385 0.040 Uiso 1 1 calc R . . C4 C 0.5254(4) 1.0187(3) 0.17595(19) 0.0371(10) Uani 1 1 d . . . H4 H 0.5278 1.0787 0.1949 0.044 Uiso 1 1 calc R . . C5 C 0.5742(4) 1.0036(3) 0.12319(18) 0.0331(10) Uani 1 1 d . . . H5 H 0.6135 1.0522 0.1054 0.040 Uiso 1 1 calc R . . C6 C 0.5663(4) 0.9176(3) 0.09566(17) 0.0288(9) Uani 1 1 d . . . C7 C 0.6143(4) 0.9042(3) 0.03669(18) 0.0331(10) Uani 1 1 d . . . C8 C 0.4034(4) 0.6014(3) 0.18604(16) 0.0259(9) Uani 1 1 d . . . C9 C 0.2897(4) 0.5946(3) 0.21485(16) 0.0282(9) Uani 1 1 d . . . H9 H 0.2324 0.6530 0.2272 0.034 Uiso 1 1 calc R . . C10 C 0.2608(4) 0.5021(3) 0.22539(16) 0.0277(9) Uani 1 1 d . . . H10 H 0.1831 0.4972 0.2448 0.033 Uiso 1 1 calc R . . C11 C 0.3449(4) 0.4169(3) 0.20771(16) 0.0263(9) Uani 1 1 d . . . C12 C 0.3276(4) 0.3093(3) 0.21331(16) 0.0276(9) Uani 1 1 d . . . H12 H 0.2454 0.3028 0.2330 0.033 Uiso 1 1 calc R . . C13 C 0.3393(4) 0.2677(3) 0.15460(16) 0.0275(9) Uani 1 1 d . . . C14 C 0.2538(4) 0.2207(3) 0.12848(17) 0.0314(9) Uani 1 1 d . . . H14 H 0.1775 0.2114 0.1476 0.038 Uiso 1 1 calc R . . C15 C 0.2786(4) 0.1868(3) 0.07448(17) 0.0308(9) Uani 1 1 d . . . H15 H 0.2201 0.1533 0.0569 0.037 Uiso 1 1 calc R . . C16 C 0.3894(4) 0.2017(3) 0.04570(16) 0.0285(9) Uani 1 1 d . . . C17 C 0.4785(4) 0.2465(3) 0.07246(17) 0.0278(9) Uani 1 1 d . . . H17 H 0.5554 0.2551 0.0536 0.033 Uiso 1 1 calc R . . C18 C 0.4535(4) 0.2782(3) 0.12646(16) 0.0259(9) Uani 1 1 d . . . C19 C 0.5419(4) 0.3259(3) 0.16247(16) 0.0254(8) Uani 1 1 d . . . H19 H 0.6242 0.3323 0.1429 0.030 Uiso 1 1 calc R . . C20 C 0.4599(4) 0.4250(3) 0.17970(16) 0.0248(8) Uani 1 1 d . . . C21 C 0.4887(4) 0.5165(3) 0.16917(16) 0.0257(8) Uani 1 1 d . . . H21 H 0.5671 0.5215 0.1504 0.031 Uiso 1 1 calc R . . C22 C 0.4478(4) 0.2533(3) 0.24201(17) 0.0276(9) Uani 1 1 d . . . C23 C 0.5627(4) 0.2626(3) 0.21468(17) 0.0280(9) Uani 1 1 d . . . C24 C 0.6804(4) 0.2139(3) 0.23396(19) 0.0386(11) Uani 1 1 d . . . H24 H 0.7583 0.2216 0.2156 0.046 Uiso 1 1 calc R . . C25 C 0.6832(5) 0.1540(4) 0.2803(2) 0.0469(12) Uani 1 1 d . . . H25 H 0.7633 0.1197 0.2939 0.056 Uiso 1 1 calc R . . C26 C 0.5681(5) 0.1438(4) 0.3072(2) 0.0470(12) Uani 1 1 d . . . H26 H 0.5709 0.1022 0.3389 0.056 Uiso 1 1 calc R . . C27 C 0.4496(5) 0.1936(3) 0.28847(18) 0.0380(10) Uani 1 1 d . . . H27 H 0.3718 0.1867 0.3071 0.046 Uiso 1 1 calc R . . C56 C 0.9057(4) 0.5078(3) 0.48720(17) 0.0281(9) Uani 1 1 d . . . C57 C 0.7787(4) 0.5193(3) 0.46923(16) 0.0283(9) Uani 1 1 d . . . C58 C 0.7448(4) 0.4508(3) 0.43166(17) 0.0330(10) Uani 1 1 d . . . H58 H 0.8081 0.3951 0.4201 0.040 Uiso 1 1 calc R . . C59 C 0.6237(4) 0.4624(3) 0.41150(17) 0.0338(10) Uani 1 1 d . . . H59 H 0.6041 0.4151 0.3862 0.041 Uiso 1 1 calc R . . C60 C 0.5263(4) 0.5447(3) 0.42789(17) 0.0334(10) Uani 1 1 d . . . C61 C 0.5578(4) 0.6112(3) 0.46724(17) 0.0301(9) Uani 1 1 d . . . H61 H 0.4935 0.6651 0.4802 0.036 Uiso 1 1 calc R . . C62 C 0.6797(4) 0.5989(3) 0.48674(17) 0.0293(9) Uani 1 1 d . . . H62 H 0.6988 0.6451 0.5129 0.035 Uiso 1 1 calc R . . C63 C 0.3803(4) 0.5066(4) 0.35631(19) 0.0428(12) Uani 1 1 d . . . H63A H 0.4600 0.4900 0.3330 0.051 Uiso 1 1 calc R . . H63B H 0.3146 0.5506 0.3343 0.051 Uiso 1 1 calc R . . C64 C 0.3332(5) 0.4127(4) 0.3695(2) 0.0476(12) Uani 1 1 d . . . H64A H 0.4028 0.3644 0.3859 0.071 Uiso 1 1 calc R . . H64B H 0.3063 0.3853 0.3352 0.071 Uiso 1 1 calc R . . H64C H 0.2598 0.4272 0.3958 0.071 Uiso 1 1 calc R . . C65 C 0.3012(4) 0.6373(3) 0.42602(19) 0.0389(11) Uani 1 1 d . . . H65A H 0.3093 0.6446 0.4666 0.047 Uiso 1 1 calc R . . H65B H 0.2186 0.6162 0.4197 0.047 Uiso 1 1 calc R . . C66 C 0.2978(5) 0.7367(4) 0.3985(2) 0.0509(13) Uani 1 1 d . . . H66A H 0.3697 0.7651 0.4114 0.076 Uiso 1 1 calc R . . H66B H 0.2162 0.7814 0.4082 0.076 Uiso 1 1 calc R . . H66C H 0.3053 0.7281 0.3582 0.076 Uiso 1 1 calc R . . C67 C 0.4989(4) 0.5624(3) 0.02387(16) 0.0268(9) Uani 1 1 d . . . C68 C 0.4093(4) 0.4952(3) 0.01516(16) 0.0273(9) Uani 1 1 d . . . C69 C 0.2857(4) 0.4888(3) 0.03619(16) 0.0287(9) Uani 1 1 d . . . C70 C 0.2225(4) 0.5529(3) 0.07800(17) 0.0300(9) Uani 1 1 d . . . H70 H 0.2625 0.6036 0.0917 0.036 Uiso 1 1 calc R . . C71 C 0.1044(4) 0.5434(3) 0.09922(18) 0.0348(10) Uani 1 1 d . . . H71 H 0.0647 0.5866 0.1280 0.042 Uiso 1 1 calc R . . C72 C 0.0402(4) 0.4695(3) 0.07867(17) 0.0328(10) Uani 1 1 d . . . C73 C 0.1012(4) 0.4089(3) 0.03512(17) 0.0319(9) Uani 1 1 d . . . H73 H 0.0587 0.3614 0.0193 0.038 Uiso 1 1 calc R . . C74 C 0.2211(4) 0.4169(3) 0.01497(17) 0.0305(9) Uani 1 1 d . . . H74 H 0.2613 0.3734 -0.0137 0.037 Uiso 1 1 calc R . . C75 C -0.1303(4) 0.5122(4) 0.15040(18) 0.0421(11) Uani 1 1 d . . . H75A H -0.0597 0.5179 0.1756 0.051 Uiso 1 1 calc R . . H75B H -0.1873 0.4733 0.1699 0.051 Uiso 1 1 calc R . . C76 C -0.2080(4) 0.6166(4) 0.13820(19) 0.0449(12) Uani 1 1 d . . . H76A H -0.1510 0.6568 0.1210 0.067 Uiso 1 1 calc R . . H76B H -0.2450 0.6478 0.1730 0.067 Uiso 1 1 calc R . . H76C H -0.2775 0.6116 0.1129 0.067 Uiso 1 1 calc R . . C77 C -0.1474(4) 0.3889(3) 0.07762(19) 0.0379(10) Uani 1 1 d . . . H77A H -0.1332 0.3857 0.0368 0.045 Uiso 1 1 calc R . . H77B H -0.2405 0.4138 0.0851 0.045 Uiso 1 1 calc R . . C78 C -0.1095(5) 0.2845(4) 0.1015(2) 0.0450(12) Uani 1 1 d . . . H78A H -0.0232 0.2538 0.0875 0.067 Uiso 1 1 calc R . . H78B H -0.1715 0.2447 0.0902 0.067 Uiso 1 1 calc R . . H78C H -0.1094 0.2881 0.1421 0.067 Uiso 1 1 calc R . . C79 C 0.1429(5) 0.9087(4) 0.0452(2) 0.0552(14) Uani 1 1 d . . . H79 H 0.1650 0.9490 0.0131 0.066 Uiso 1 1 calc R . . Cl1 Cl 0.15160(18) 0.97523(12) 0.10616(7) 0.0755(5) Uani 1 1 d . . . Cl2 Cl 0.25555(14) 0.79682(11) 0.04602(7) 0.0645(4) Uani 1 1 d . . . Cl3 Cl -0.01197(14) 0.88598(13) 0.03590(7) 0.0757(5) Uani 1 1 d . . . C80 C 0.8223(10) 0.0682(6) 0.4505(3) 0.049(3) Uani 0.538(3) 1 d PD A 1 H80A H 0.7539 0.0368 0.4636 0.059 Uiso 0.538(3) 1 d PR A 1 Cl4 Cl 0.8895(4) 0.0097(3) 0.38912(18) 0.0572(10) Uani 0.538(3) 1 d PD A 1 Cl5 Cl 0.7593(4) 0.1927(2) 0.43762(13) 0.0899(14) Uani 0.538(3) 1 d PD A 1 Cl6 Cl 0.9393(3) 0.0552(3) 0.50086(12) 0.0760(10) Uani 0.538(3) 1 d PD . 1 Cl7 Cl 0.8335(4) 0.0300(4) 0.3967(2) 0.0511(11) Uani 0.462(3) 1 d PD A 2 Cl8 Cl 0.8784(3) 0.1955(2) 0.45891(13) 0.0549(9) Uani 0.462(3) 1 d PD A 2 Cl9 Cl 0.6200(3) 0.1749(2) 0.44110(12) 0.0555(9) Uani 0.462(3) 1 d PD A 2 C81 C 0.7768(8) 0.1114(6) 0.4515(4) 0.043(3) Uani 0.462(3) 1 d PD A 2 H81A H 0.7778 0.0735 0.4851 0.052 Uiso 0.462(3) 1 d PR A 2 N4 N 0.7821(4) 0.8363(3) 0.53345(15) 0.0341(8) Uani 1 1 d . . . N5 N 0.8635(3) 0.8312(3) 0.63920(15) 0.0333(8) Uani 1 1 d . . . N6 N 1.0128(3) 0.6619(3) 0.67369(14) 0.0331(8) Uani 1 1 d . . . H6A H 0.9630 0.6931 0.6461 0.050 Uiso 1 1 d R . . O3 O 0.6660(3) 0.9934(2) 0.54685(14) 0.0515(9) Uani 1 1 d . . . O4 O 1.0297(3) 0.7300(2) 0.75863(13) 0.0438(8) Uani 1 1 d . . . C28 C 0.7380(4) 0.9190(3) 0.56384(19) 0.0387(11) Uani 1 1 d . . . C29 C 0.7864(4) 0.9158(3) 0.62199(19) 0.0364(10) Uani 1 1 d . . . C30 C 0.7521(5) 0.9992(3) 0.6544(2) 0.0444(12) Uani 1 1 d . . . H30 H 0.6965 1.0568 0.6409 0.053 Uiso 1 1 calc R . . C31 C 0.8004(5) 0.9975(4) 0.7073(2) 0.0486(13) Uani 1 1 d . . . H31 H 0.7789 1.0543 0.7305 0.058 Uiso 1 1 calc R . . C32 C 0.8811(5) 0.9117(4) 0.7263(2) 0.0437(12) Uani 1 1 d . . . H32 H 0.9162 0.9085 0.7623 0.052 Uiso 1 1 calc R . . C33 C 0.9080(4) 0.8314(3) 0.69050(19) 0.0349(10) Uani 1 1 d . . . C34 C 0.9902(4) 0.7364(3) 0.71089(18) 0.0350(10) Uani 1 1 d . . . C35 C 0.7607(4) 0.8245(3) 0.47676(18) 0.0331(10) Uani 1 1 d . . . C36 C 0.8660(4) 0.7744(3) 0.44410(18) 0.0319(9) Uani 1 1 d . . . H36 H 0.9485 0.7551 0.4599 0.038 Uiso 1 1 calc R . . C37 C 0.8488(4) 0.7537(3) 0.38962(18) 0.0313(9) Uani 1 1 d . . . C38 C 0.9523(4) 0.7010(3) 0.34959(17) 0.0288(9) Uani 1 1 d . . . H38 H 1.0398 0.6854 0.3661 0.035 Uiso 1 1 calc R . . C39 C 0.9053(4) 0.6097(3) 0.33099(17) 0.0290(9) Uani 1 1 d . . . C40 C 0.9726(4) 0.5138(3) 0.33635(17) 0.0305(9) Uani 1 1 d . . . H40 H 1.0541 0.5005 0.3534 0.037 Uiso 1 1 calc R . . C41 C 0.9191(4) 0.4362(3) 0.31635(17) 0.0311(9) Uani 1 1 d . . . C42 C 0.7993(4) 0.4553(3) 0.29145(16) 0.0337(10) Uani 1 1 d . . . H42 H 0.7638 0.4023 0.2775 0.040 Uiso 1 1 calc R . . C43 C 0.7319(4) 0.5534(3) 0.28721(18) 0.0344(10) Uani 1 1 d . . . H43 H 0.6503 0.5672 0.2702 0.041 Uiso 1 1 calc R . . C44 C 0.7834(4) 0.6299(3) 0.30759(17) 0.0336(10) Uani 1 1 d . . . C45 C 0.7253(4) 0.7422(3) 0.30681(18) 0.0345(10) Uani 1 1 d . . . H45 H 0.6378 0.7580 0.2904 0.041 Uiso 1 1 calc R . . C46 C 0.7268(4) 0.7786(3) 0.36637(19) 0.0341(10) Uani 1 1 d . . . C47 C 0.6245(4) 0.8323(3) 0.39745(19) 0.0368(10) Uani 1 1 d . . . H47 H 0.5427 0.8529 0.3812 0.044 Uiso 1 1 calc R . . C48 C 0.6420(4) 0.8558(3) 0.4523(2) 0.0387(11) Uani 1 1 d . . . H48 H 0.5723 0.8936 0.4733 0.046 Uiso 1 1 calc R . . C49 C 0.9470(4) 0.7658(3) 0.29791(18) 0.0324(9) Uani 1 1 d . . . C50 C 0.8244(4) 0.7870(3) 0.27459(18) 0.0344(10) Uani 1 1 d . . . C51 C 0.8058(5) 0.8415(4) 0.2262(2) 0.0448(12) Uani 1 1 d . . . H51 H 0.7227 0.8571 0.2106 0.054 Uiso 1 1 calc R . . C52 C 0.9084(5) 0.8735(4) 0.2006(2) 0.0497(13) Uani 1 1 d . . . H52 H 0.8960 0.9104 0.1670 0.060 Uiso 1 1 calc R . . C53 C 1.0286(5) 0.8521(4) 0.2235(2) 0.0447(12) Uani 1 1 d . . . H53 H 1.0989 0.8737 0.2054 0.054 Uiso 1 1 calc R . . C54 C 1.0478(4) 0.7993(3) 0.27277(18) 0.0345(10) Uani 1 1 d . . . H54 H 1.1303 0.7863 0.2890 0.041 Uiso 1 1 calc R . . H3A H 0.544(5) 0.790(4) 0.0281(19) 0.039(13) Uiso 1 1 d . . . H4A H 0.835(5) 0.788(4) 0.5464(19) 0.040(14) Uiso 1 1 d . . . C55 C 0.9744(4) 0.5622(3) 0.52445(17) 0.0292(9) Uani 1 1 d . . . O5 O 0.9431(3) 0.6366(2) 0.55470(12) 0.0325(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0345(19) 0.0198(17) 0.0283(18) 0.0006(14) 0.0046(14) -0.0078(14) N2 0.0291(18) 0.0212(17) 0.034(2) 0.0045(14) -0.0042(15) -0.0083(14) N3 0.039(2) 0.0259(18) 0.028(2) 0.0024(15) 0.0015(16) -0.0161(16) N7 0.0262(18) 0.049(2) 0.032(2) 0.0012(17) -0.0046(15) -0.0087(17) N8 0.0285(19) 0.051(2) 0.031(2) 0.0031(17) 0.0039(15) -0.0131(17) O1 0.0462(18) 0.0310(16) 0.0337(18) -0.0064(13) 0.0096(14) -0.0147(14) O2 0.059(2) 0.0318(17) 0.0425(19) 0.0051(14) 0.0031(15) -0.0253(16) O6 0.0348(16) 0.0298(15) 0.0293(16) 0.0001(12) 0.0034(12) -0.0096(13) C1 0.026(2) 0.025(2) 0.032(2) -0.0010(17) -0.0009(18) -0.0056(17) C2 0.028(2) 0.0185(19) 0.032(2) -0.0007(16) -0.0033(17) -0.0037(16) C3 0.034(2) 0.030(2) 0.035(2) -0.0047(18) 0.0033(18) -0.0065(19) C4 0.048(3) 0.020(2) 0.044(3) -0.0020(18) 0.001(2) -0.0061(19) C5 0.041(2) 0.021(2) 0.039(3) 0.0059(18) -0.007(2) -0.0110(18) C6 0.034(2) 0.025(2) 0.028(2) 0.0025(17) -0.0037(17) -0.0076(18) C7 0.040(2) 0.025(2) 0.036(2) 0.0043(18) -0.0075(19) -0.0083(19) C8 0.031(2) 0.026(2) 0.023(2) 0.0000(16) -0.0029(16) -0.0115(17) C9 0.032(2) 0.029(2) 0.024(2) -0.0036(16) 0.0023(17) -0.0063(18) C10 0.028(2) 0.035(2) 0.022(2) 0.0015(17) 0.0014(16) -0.0104(18) C11 0.031(2) 0.022(2) 0.028(2) 0.0061(16) -0.0002(17) -0.0113(17) C12 0.026(2) 0.027(2) 0.032(2) 0.0026(17) 0.0024(17) -0.0116(17) C13 0.030(2) 0.024(2) 0.029(2) 0.0044(16) -0.0007(17) -0.0077(17) C14 0.032(2) 0.033(2) 0.033(2) 0.0092(18) -0.0012(18) -0.0137(18) C15 0.032(2) 0.030(2) 0.035(2) 0.0023(18) -0.0044(18) -0.0150(18) C16 0.037(2) 0.023(2) 0.027(2) 0.0035(16) 0.0020(18) -0.0090(18) C17 0.029(2) 0.023(2) 0.033(2) 0.0064(17) 0.0020(17) -0.0087(17) C18 0.027(2) 0.0210(19) 0.032(2) 0.0032(16) 0.0007(17) -0.0105(16) C19 0.026(2) 0.026(2) 0.026(2) 0.0052(16) 0.0021(16) -0.0109(17) C20 0.027(2) 0.025(2) 0.026(2) 0.0024(16) -0.0018(16) -0.0104(17) C21 0.024(2) 0.029(2) 0.027(2) -0.0024(16) 0.0013(16) -0.0110(17) C22 0.032(2) 0.023(2) 0.031(2) 0.0036(16) -0.0023(17) -0.0112(17) C23 0.034(2) 0.021(2) 0.032(2) -0.0004(16) -0.0033(18) -0.0118(17) C24 0.033(2) 0.037(2) 0.048(3) 0.006(2) -0.006(2) -0.014(2) C25 0.039(3) 0.044(3) 0.057(3) 0.019(2) -0.013(2) -0.006(2) C26 0.056(3) 0.045(3) 0.042(3) 0.018(2) -0.014(2) -0.016(2) C27 0.045(3) 0.036(2) 0.037(3) 0.0071(19) 0.000(2) -0.018(2) C56 0.029(2) 0.026(2) 0.030(2) 0.0093(17) -0.0015(17) -0.0079(17) C57 0.028(2) 0.032(2) 0.028(2) 0.0111(17) -0.0036(17) -0.0112(18) C58 0.030(2) 0.036(2) 0.034(2) 0.0036(19) 0.0020(18) -0.0078(19) C59 0.035(2) 0.036(2) 0.032(2) 0.0010(19) 0.0009(19) -0.012(2) C60 0.030(2) 0.041(2) 0.031(2) 0.0102(19) -0.0047(18) -0.012(2) C61 0.027(2) 0.032(2) 0.032(2) 0.0051(18) -0.0019(17) -0.0067(18) C62 0.030(2) 0.030(2) 0.029(2) 0.0036(17) 0.0004(17) -0.0090(18) C63 0.032(2) 0.064(3) 0.036(3) 0.004(2) -0.006(2) -0.016(2) C64 0.046(3) 0.059(3) 0.038(3) -0.001(2) -0.010(2) -0.011(2) C65 0.027(2) 0.050(3) 0.041(3) 0.008(2) -0.0061(19) -0.011(2) C66 0.042(3) 0.050(3) 0.063(3) 0.020(3) -0.011(2) -0.012(2) C67 0.027(2) 0.029(2) 0.024(2) 0.0032(16) 0.0009(16) -0.0060(17) C68 0.030(2) 0.030(2) 0.024(2) 0.0067(17) -0.0024(17) -0.0091(18) C69 0.027(2) 0.033(2) 0.027(2) 0.0062(17) -0.0009(17) -0.0070(18) C70 0.024(2) 0.038(2) 0.029(2) -0.0042(18) -0.0027(17) -0.0049(18) C71 0.030(2) 0.044(3) 0.030(2) -0.0048(19) -0.0004(18) -0.0053(19) C72 0.026(2) 0.046(3) 0.028(2) 0.0108(19) -0.0023(17) -0.0129(19) C73 0.030(2) 0.032(2) 0.035(2) 0.0056(18) -0.0019(18) -0.0089(18) C74 0.031(2) 0.031(2) 0.029(2) 0.0057(17) 0.0029(17) -0.0052(18) C75 0.037(2) 0.061(3) 0.031(3) 0.003(2) 0.002(2) -0.018(2) C76 0.032(2) 0.068(3) 0.037(3) -0.007(2) 0.007(2) -0.015(2) C77 0.027(2) 0.052(3) 0.036(3) 0.008(2) 0.0020(18) -0.012(2) C78 0.036(3) 0.047(3) 0.054(3) 0.012(2) -0.003(2) -0.014(2) C79 0.055(3) 0.054(3) 0.061(4) 0.018(3) -0.005(3) -0.021(3) Cl1 0.1089(13) 0.0583(9) 0.0668(10) 0.0052(7) 0.0162(9) -0.0369(9) Cl2 0.0562(8) 0.0553(8) 0.0821(11) 0.0148(7) -0.0055(7) -0.0108(7) Cl3 0.0472(8) 0.0889(12) 0.0948(12) 0.0305(9) -0.0122(8) -0.0220(8) C80 0.077(9) 0.048(8) 0.031(6) 0.010(5) -0.019(6) -0.029(7) Cl4 0.074(3) 0.045(2) 0.0538(19) 0.0128(15) -0.004(2) -0.015(2) Cl5 0.156(4) 0.0423(17) 0.068(2) 0.0062(14) -0.020(2) -0.0081(18) Cl6 0.0630(18) 0.103(2) 0.069(2) 0.0131(17) -0.0184(14) -0.0313(16) Cl7 0.050(2) 0.040(2) 0.060(3) 0.0062(16) -0.007(2) 0.0001(19) Cl8 0.0493(17) 0.0522(17) 0.066(2) -0.0060(14) 0.0008(14) -0.0161(13) Cl9 0.0396(15) 0.068(2) 0.0564(18) -0.0030(14) 0.0018(12) -0.0058(13) C81 0.058(8) 0.038(9) 0.035(6) 0.015(6) -0.003(6) -0.013(6) N4 0.038(2) 0.0250(19) 0.036(2) 0.0051(16) 0.0057(17) 0.0011(17) N5 0.0332(19) 0.032(2) 0.036(2) 0.0033(15) 0.0080(16) -0.0108(16) N6 0.038(2) 0.0305(19) 0.031(2) 0.0024(15) -0.0036(16) -0.0069(16) O3 0.062(2) 0.0354(19) 0.049(2) 0.0096(15) 0.0094(17) 0.0104(17) O4 0.0411(18) 0.056(2) 0.0361(19) -0.0057(15) -0.0051(14) -0.0130(16) C28 0.042(3) 0.033(2) 0.039(3) 0.010(2) 0.011(2) -0.004(2) C29 0.041(3) 0.024(2) 0.043(3) 0.0020(19) 0.015(2) -0.0063(19) C30 0.050(3) 0.030(2) 0.053(3) -0.001(2) 0.021(2) -0.012(2) C31 0.049(3) 0.037(3) 0.062(4) -0.015(2) 0.020(3) -0.016(2) C32 0.051(3) 0.044(3) 0.041(3) -0.011(2) 0.009(2) -0.023(2) C33 0.031(2) 0.033(2) 0.043(3) -0.0038(19) 0.007(2) -0.0141(19) C34 0.033(2) 0.039(2) 0.036(3) -0.004(2) 0.0022(19) -0.015(2) C35 0.035(2) 0.024(2) 0.040(3) 0.0059(18) 0.0056(19) -0.0063(18) C36 0.030(2) 0.025(2) 0.039(3) 0.0070(18) 0.0033(19) -0.0046(18) C37 0.029(2) 0.029(2) 0.036(2) 0.0087(18) 0.0003(18) -0.0059(18) C38 0.024(2) 0.029(2) 0.033(2) 0.0063(17) -0.0027(17) -0.0035(17) C39 0.029(2) 0.032(2) 0.027(2) 0.0096(17) -0.0027(17) -0.0088(18) C40 0.027(2) 0.034(2) 0.030(2) 0.0073(18) -0.0018(17) -0.0051(18) C41 0.035(2) 0.031(2) 0.027(2) 0.0045(17) -0.0001(18) -0.0078(19) C42 0.044(3) 0.039(2) 0.022(2) 0.0034(18) -0.0037(18) -0.019(2) C43 0.030(2) 0.042(3) 0.034(2) 0.0049(19) -0.0065(18) -0.012(2) C44 0.030(2) 0.040(2) 0.031(2) 0.0090(19) -0.0050(18) -0.0071(19) C45 0.025(2) 0.040(2) 0.039(3) 0.013(2) -0.0055(18) -0.0079(19) C46 0.028(2) 0.031(2) 0.043(3) 0.0150(19) -0.0028(19) -0.0063(18) C47 0.024(2) 0.037(2) 0.048(3) 0.012(2) -0.0015(19) -0.0030(19) C48 0.030(2) 0.029(2) 0.055(3) 0.009(2) 0.010(2) -0.0003(19) C49 0.033(2) 0.031(2) 0.033(2) 0.0070(18) -0.0024(18) -0.0065(19) C50 0.031(2) 0.034(2) 0.037(2) 0.0111(19) -0.0035(19) -0.0043(19) C51 0.040(3) 0.050(3) 0.045(3) 0.019(2) -0.007(2) -0.010(2) C52 0.048(3) 0.059(3) 0.043(3) 0.024(2) -0.003(2) -0.015(3) C53 0.048(3) 0.045(3) 0.044(3) 0.017(2) 0.002(2) -0.017(2) C54 0.033(2) 0.034(2) 0.037(3) 0.0041(19) -0.0017(19) -0.0092(19) C55 0.030(2) 0.031(2) 0.028(2) 0.0094(17) -0.0029(17) -0.0087(18) O5 0.0337(16) 0.0280(15) 0.0350(17) 0.0014(13) -0.0035(13) -0.0038(13) _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 N1 C1 1.346(5) . ? N1 C8 1.424(5) . ? N1 H1 0.9100 . ? N2 C6 1.344(5) . ? N2 C2 1.347(5) . ? N3 C7 1.362(5) . ? N3 C16 1.409(5) 2_665 ? N3 H3A 0.82(5) . ? N7 C60 1.364(5) . ? N7 C65 1.458(6) . ? N7 C63 1.463(6) . ? N8 C72 1.354(5) . ? N8 C75 1.458(6) . ? N8 C77 1.459(6) . ? O1 C1 1.219(5) . ? O2 C7 1.224(5) . ? O6 C67 1.237(5) . ? C1 C2 1.508(5) . ? C2 C3 1.385(5) . ? C3 C4 1.389(6) . ? C3 H3 0.9500 . ? C4 C5 1.361(6) . ? C4 H4 0.9500 . ? C5 C6 1.378(6) . ? C5 H5 0.9500 . ? C6 C7 1.496(6) . ? C8 C21 1.383(6) . ? C8 C9 1.393(6) . ? C9 C10 1.387(5) . ? C9 H9 0.9500 . ? C10 C11 1.386(6) . ? C10 H10 0.9500 . ? C11 C20 1.401(5) . ? C11 C12 1.532(5) . ? C12 C13 1.521(6) . ? C12 C22 1.530(5) . ? C12 H12 1.0000 . ? C13 C14 1.378(5) . ? C13 C18 1.404(5) . ? C14 C15 1.385(6) . ? C14 H14 0.9500 . ? C15 C16 1.398(6) . ? C15 H15 0.9500 . ? C16 C17 1.396(6) . ? C16 N3 1.409(5) 2_665 ? C17 C18 1.376(6) . ? C17 H17 0.9500 . ? C18 C19 1.531(5) . ? C19 C20 1.519(5) . ? C19 C23 1.522(5) . ? C19 H19 1.0000 . ? C20 C21 1.374(5) . ? C21 H21 0.9500 . ? C22 C27 1.383(6) . ? C22 C23 1.397(6) . ? C23 C24 1.383(6) . ? C24 C25 1.382(6) . ? C24 H24 0.9500 . ? C25 C26 1.396(7) . ? C25 H25 0.9500 . ? C26 C27 1.390(6) . ? C26 H26 0.9500 . ? C27 H27 0.9500 . ? C56 C57 1.402(5) . ? C56 C55 1.456(6) 2_766 ? C56 C55 1.466(6) . ? C57 C58 1.412(6) . ? C57 C62 1.416(6) . ? C58 C59 1.361(6) . ? C58 H58 0.9500 . ? C59 C60 1.423(6) . ? C59 H59 0.9500 . ? C60 C61 1.412(6) . ? C61 C62 1.363(5) . ? C61 H61 0.9500 . ? C62 H62 0.9500 . ? C63 C64 1.503(7) . ? C63 H63A 0.9900 . ? C63 H63B 0.9900 . ? C64 H64A 0.9800 . ? C64 H64B 0.9800 . ? C64 H64C 0.9800 . ? C65 C66 1.511(6) . ? C65 H65A 0.9900 . ? C65 H65B 0.9900 . ? C66 H66A 0.9800 . ? C66 H66B 0.9800 . ? C66 H66C 0.9800 . ? C67 C68 1.454(6) 2_665 ? C67 C68 1.469(5) . ? C68 C69 1.411(6) . ? C68 C67 1.454(6) 2_665 ? C69 C70 1.408(6) . ? C69 C74 1.413(6) . ? C70 C71 1.369(6) . ? C70 H70 0.9500 . ? C71 C72 1.427(6) . ? C71 H71 0.9500 . ? C72 C73 1.406(6) . ? C73 C74 1.372(6) . ? C73 H73 0.9500 . ? C74 H74 0.9500 . ? C75 C76 1.538(7) . ? C75 H75A 0.9900 . ? C75 H75B 0.9900 . ? C76 H76A 0.9800 . ? C76 H76B 0.9800 . ? C76 H76C 0.9800 . ? C77 C78 1.526(6) . ? C77 H77A 0.9900 . ? C77 H77B 0.9900 . ? C78 H78A 0.9800 . ? C78 H78B 0.9800 . ? C78 H78C 0.9800 . ? C79 Cl1 1.748(6) . ? C79 Cl3 1.749(5) . ? C79 Cl2 1.751(6) . ? C79 H79 1.0000 . ? C80 Cl6 1.738(7) . ? C80 Cl5 1.740(8) . ? C80 Cl4 1.754(8) . ? C80 H80A 0.9600 . ? C80 H81A 0.9427 . ? Cl6 Cl6 1.785(7) 2_756 ? Cl6 H81A 1.7302 . ? Cl7 C81 1.750(8) . ? Cl7 H80A 1.7928 . ? Cl8 C81 1.741(8) . ? Cl9 C81 1.740(8) . ? C81 H80A 1.1354 . ? C81 H81A 0.9599 . ? N4 C28 1.353(6) . ? N4 C35 1.405(6) . ? N4 H4A 0.84(5) . ? N5 C33 1.333(6) . ? N5 C29 1.353(5) . ? N6 C34 1.347(5) . ? N6 C41 1.421(5) 2_766 ? N6 H6A 0.9101 . ? O3 C28 1.224(5) . ? O4 C34 1.230(5) . ? C28 C29 1.501(7) . ? C29 C30 1.375(6) . ? C30 C31 1.381(7) . ? C30 H30 0.9500 . ? C31 C32 1.397(7) . ? C31 H31 0.9500 . ? C32 C33 1.385(6) . ? C32 H32 0.9500 . ? C33 C34 1.507(6) . ? C35 C48 1.390(6) . ? C35 C36 1.413(6) . ? C36 C37 1.369(6) . ? C36 H36 0.9500 . ? C37 C46 1.399(6) . ? C37 C38 1.516(6) . ? C38 C39 1.514(6) . ? C38 C49 1.523(6) . ? C38 H38 1.0000 . ? C39 C40 1.377(6) . ? C39 C44 1.398(6) . ? C40 C41 1.396(6) . ? C40 H40 0.9500 . ? C41 C42 1.394(6) . ? C41 N6 1.421(5) 2_766 ? C42 C43 1.402(6) . ? C42 H42 0.9500 . ? C43 C44 1.375(6) . ? C43 H43 0.9500 . ? C44 C45 1.547(6) . ? C45 C50 1.515(6) . ? C45 C46 1.523(6) . ? C45 H45 1.0000 . ? C46 C47 1.389(6) . ? C47 C48 1.387(7) . ? C47 H47 0.9500 . ? C48 H48 0.9500 . ? C49 C54 1.370(6) . ? C49 C50 1.403(6) . ? C50 C51 1.380(6) . ? C51 C52 1.382(7) . ? C51 H51 0.9500 . ? C52 C53 1.377(7) . ? C52 H52 0.9500 . ? C53 C54 1.387(6) . ? C53 H53 0.9500 . ? C54 H54 0.9500 . ? C55 O5 1.245(5) . ? C55 C56 1.456(6) 2_766 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C8 126.5(3) . . ? C1 N1 H1 117.8 . . ? C8 N1 H1 115.5 . . ? C6 N2 C2 116.9(3) . . ? C7 N3 C16 126.4(4) . 2_665 ? C7 N3 H3A 118(3) . . ? C16 N3 H3A 115(3) 2_665 . ? C60 N7 C65 122.2(4) . . ? C60 N7 C63 121.8(4) . . ? C65 N7 C63 115.8(3) . . ? C72 N8 C75 121.5(4) . . ? C72 N8 C77 121.9(4) . . ? C75 N8 C77 116.5(3) . . ? O1 C1 N1 124.9(4) . . ? O1 C1 C2 121.3(3) . . ? N1 C1 C2 113.7(3) . . ? N2 C2 C3 123.4(4) . . ? N2 C2 C1 117.6(3) . . ? C3 C2 C1 119.0(4) . . ? C2 C3 C4 118.1(4) . . ? C2 C3 H3 121.0 . . ? C4 C3 H3 121.0 . . ? C5 C4 C3 119.0(4) . . ? C5 C4 H4 120.5 . . ? C3 C4 H4 120.5 . . ? C4 C5 C6 119.8(4) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? N2 C6 C5 122.8(4) . . ? N2 C6 C7 118.0(4) . . ? C5 C6 C7 119.2(4) . . ? O2 C7 N3 124.6(4) . . ? O2 C7 C6 120.7(4) . . ? N3 C7 C6 114.7(4) . . ? C21 C8 C9 120.4(4) . . ? C21 C8 N1 116.6(3) . . ? C9 C8 N1 122.8(4) . . ? C10 C9 C8 119.6(4) . . ? C10 C9 H9 120.2 . . ? C8 C9 H9 120.2 . . ? C11 C10 C9 120.2(4) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C10 C11 C20 119.4(3) . . ? C10 C11 C12 127.9(4) . . ? C20 C11 C12 112.7(3) . . ? C13 C12 C22 104.5(3) . . ? C13 C12 C11 105.8(3) . . ? C22 C12 C11 106.1(3) . . ? C13 C12 H12 113.2 . . ? C22 C12 H12 113.2 . . ? C11 C12 H12 113.2 . . ? C14 C13 C18 119.3(4) . . ? C14 C13 C12 127.4(4) . . ? C18 C13 C12 113.4(3) . . ? C13 C14 C15 120.3(4) . . ? C13 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? C14 C15 C16 120.2(4) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C17 C16 C15 119.8(4) . . ? C17 C16 N3 117.4(4) . 2_665 ? C15 C16 N3 122.9(4) . 2_665 ? C18 C17 C16 119.3(4) . . ? C18 C17 H17 120.4 . . ? C16 C17 H17 120.4 . . ? C17 C18 C13 121.1(4) . . ? C17 C18 C19 126.2(3) . . ? C13 C18 C19 112.8(3) . . ? C20 C19 C23 106.8(3) . . ? C20 C19 C18 104.4(3) . . ? C23 C19 C18 105.6(3) . . ? C20 C19 H19 113.1 . . ? C23 C19 H19 113.1 . . ? C18 C19 H19 113.1 . . ? C21 C20 C11 120.5(4) . . ? C21 C20 C19 125.9(3) . . ? C11 C20 C19 113.6(3) . . ? C20 C21 C8 119.8(4) . . ? C20 C21 H21 120.1 . . ? C8 C21 H21 120.1 . . ? C27 C22 C23 120.4(4) . . ? C27 C22 C12 126.2(4) . . ? C23 C22 C12 113.3(3) . . ? C24 C23 C22 120.9(4) . . ? C24 C23 C19 125.9(4) . . ? C22 C23 C19 113.2(3) . . ? C25 C24 C23 119.0(4) . . ? C25 C24 H24 120.5 . . ? C23 C24 H24 120.5 . . ? C24 C25 C26 120.0(4) . . ? C24 C25 H25 120.0 . . ? C26 C25 H25 120.0 . . ? C27 C26 C25 121.2(4) . . ? C27 C26 H26 119.4 . . ? C25 C26 H26 119.4 . . ? C22 C27 C26 118.4(4) . . ? C22 C27 H27 120.8 . . ? C26 C27 H27 120.8 . . ? C57 C56 C55 135.0(4) . 2_766 ? C57 C56 C55 135.5(4) . . ? C55 C56 C55 89.5(3) 2_766 . ? C56 C57 C58 120.4(4) . . ? C56 C57 C62 122.6(4) . . ? C58 C57 C62 117.0(4) . . ? C59 C58 C57 121.7(4) . . ? C59 C58 H58 119.1 . . ? C57 C58 H58 119.1 . . ? C58 C59 C60 120.7(4) . . ? C58 C59 H59 119.6 . . ? C60 C59 H59 119.6 . . ? N7 C60 C61 120.8(4) . . ? N7 C60 C59 121.3(4) . . ? C61 C60 C59 117.9(4) . . ? C62 C61 C60 120.6(4) . . ? C62 C61 H61 119.7 . . ? C60 C61 H61 119.7 . . ? C61 C62 C57 122.0(4) . . ? C61 C62 H62 119.0 . . ? C57 C62 H62 119.0 . . ? N7 C63 C64 113.7(4) . . ? N7 C63 H63A 108.8 . . ? C64 C63 H63A 108.8 . . ? N7 C63 H63B 108.8 . . ? C64 C63 H63B 108.8 . . ? H63A C63 H63B 107.7 . . ? C63 C64 H64A 109.5 . . ? C63 C64 H64B 109.5 . . ? H64A C64 H64B 109.5 . . ? C63 C64 H64C 109.5 . . ? H64A C64 H64C 109.5 . . ? H64B C64 H64C 109.5 . . ? N7 C65 C66 113.3(4) . . ? N7 C65 H65A 108.9 . . ? C66 C65 H65A 108.9 . . ? N7 C65 H65B 108.9 . . ? C66 C65 H65B 108.9 . . ? H65A C65 H65B 107.7 . . ? C65 C66 H66A 109.5 . . ? C65 C66 H66B 109.5 . . ? H66A C66 H66B 109.5 . . ? C65 C66 H66C 109.5 . . ? H66A C66 H66C 109.5 . . ? H66B C66 H66C 109.5 . . ? O6 C67 C68 134.7(4) . 2_665 ? O6 C67 C68 135.3(4) . . ? C68 C67 C68 90.0(3) 2_665 . ? C69 C68 C67 135.0(4) . 2_665 ? C69 C68 C67 135.0(4) . . ? C67 C68 C67 90.0(3) 2_665 . ? C70 C69 C68 122.0(4) . . ? C70 C69 C74 118.0(4) . . ? C68 C69 C74 120.0(4) . . ? C71 C70 C69 121.1(4) . . ? C71 C70 H70 119.4 . . ? C69 C70 H70 119.4 . . ? C70 C71 C72 120.9(4) . . ? C70 C71 H71 119.5 . . ? C72 C71 H71 119.5 . . ? N8 C72 C73 121.6(4) . . ? N8 C72 C71 120.9(4) . . ? C73 C72 C71 117.5(4) . . ? C74 C73 C72 121.4(4) . . ? C74 C73 H73 119.3 . . ? C72 C73 H73 119.3 . . ? C73 C74 C69 120.9(4) . . ? C73 C74 H74 119.5 . . ? C69 C74 H74 119.5 . . ? N8 C75 C76 113.2(4) . . ? N8 C75 H75A 108.9 . . ? C76 C75 H75A 108.9 . . ? N8 C75 H75B 108.9 . . ? C76 C75 H75B 108.9 . . ? H75A C75 H75B 107.8 . . ? C75 C76 H76A 109.5 . . ? C75 C76 H76B 109.5 . . ? H76A C76 H76B 109.5 . . ? C75 C76 H76C 109.5 . . ? H76A C76 H76C 109.5 . . ? H76B C76 H76C 109.5 . . ? N8 C77 C78 113.4(4) . . ? N8 C77 H77A 108.9 . . ? C78 C77 H77A 108.9 . . ? N8 C77 H77B 108.9 . . ? C78 C77 H77B 108.9 . . ? H77A C77 H77B 107.7 . . ? C77 C78 H78A 109.5 . . ? C77 C78 H78B 109.5 . . ? H78A C78 H78B 109.5 . . ? C77 C78 H78C 109.5 . . ? H78A C78 H78C 109.5 . . ? H78B C78 H78C 109.5 . . ? Cl1 C79 Cl3 111.8(3) . . ? Cl1 C79 Cl2 110.1(3) . . ? Cl3 C79 Cl2 110.2(3) . . ? Cl1 C79 H79 108.2 . . ? Cl3 C79 H79 108.2 . . ? Cl2 C79 H79 108.2 . . ? Cl6 C80 Cl5 111.1(5) . . ? Cl6 C80 Cl4 109.5(5) . . ? Cl5 C80 Cl4 109.9(5) . . ? Cl6 C80 H80A 108.7 . . ? Cl5 C80 H80A 108.8 . . ? Cl4 C80 H80A 108.8 . . ? Cl6 C80 H81A 73.8 . . ? Cl5 C80 H81A 89.7 . . ? Cl4 C80 H81A 156.2 . . ? H80A C80 H81A 50.0 . . ? C80 Cl6 Cl6 117.3(4) . 2_756 ? C80 Cl6 H81A 31.5 . . ? Cl6 Cl6 H81A 130.2 2_756 . ? C81 Cl7 H80A 37.4 . . ? Cl9 C81 Cl8 109.9(5) . . ? Cl9 C81 Cl7 111.7(5) . . ? Cl8 C81 Cl7 109.7(5) . . ? Cl9 C81 H80A 98.1 . . ? Cl8 C81 H80A 147.3 . . ? Cl7 C81 H80A 73.4 . . ? Cl9 C81 H81A 108.6 . . ? Cl8 C81 H81A 108.5 . . ? Cl7 C81 H81A 108.4 . . ? H80A C81 H81A 44.2 . . ? C28 N4 C35 125.7(4) . . ? C28 N4 H4A 121(3) . . ? C35 N4 H4A 112(3) . . ? C33 N5 C29 116.6(4) . . ? C34 N6 C41 125.9(4) . 2_766 ? C34 N6 H6A 97.7 . . ? C41 N6 H6A 135.8 2_766 . ? O3 C28 N4 124.9(5) . . ? O3 C28 C29 120.2(4) . . ? N4 C28 C29 114.9(4) . . ? N5 C29 C30 123.6(5) . . ? N5 C29 C28 117.9(4) . . ? C30 C29 C28 118.5(4) . . ? C29 C30 C31 118.5(5) . . ? C29 C30 H30 120.8 . . ? C31 C30 H30 120.8 . . ? C30 C31 C32 119.5(4) . . ? C30 C31 H31 120.2 . . ? C32 C31 H31 120.2 . . ? C33 C32 C31 117.3(5) . . ? C33 C32 H32 121.4 . . ? C31 C32 H32 121.4 . . ? N5 C33 C32 124.5(4) . . ? N5 C33 C34 117.2(4) . . ? C32 C33 C34 118.3(4) . . ? O4 C34 N6 124.4(4) . . ? O4 C34 C33 120.6(4) . . ? N6 C34 C33 115.0(4) . . ? C48 C35 N4 123.8(4) . . ? C48 C35 C36 119.3(4) . . ? N4 C35 C36 116.9(4) . . ? C37 C36 C35 119.7(4) . . ? C37 C36 H36 120.1 . . ? C35 C36 H36 120.1 . . ? C36 C37 C46 120.7(4) . . ? C36 C37 C38 125.7(4) . . ? C46 C37 C38 113.6(4) . . ? C39 C38 C37 105.2(3) . . ? C39 C38 C49 104.7(3) . . ? C37 C38 C49 106.6(3) . . ? C39 C38 H38 113.2 . . ? C37 C38 H38 113.2 . . ? C49 C38 H38 113.2 . . ? C40 C39 C44 121.0(4) . . ? C40 C39 C38 124.9(4) . . ? C44 C39 C38 114.1(4) . . ? C39 C40 C41 119.0(4) . . ? C39 C40 H40 120.5 . . ? C41 C40 H40 120.5 . . ? C42 C41 C40 120.7(4) . . ? C42 C41 N6 122.0(4) . 2_766 ? C40 C41 N6 117.2(4) . 2_766 ? C41 C42 C43 119.2(4) . . ? C41 C42 H42 120.4 . . ? C43 C42 H42 120.4 . . ? C44 C43 C42 120.2(4) . . ? C44 C43 H43 119.9 . . ? C42 C43 H43 119.9 . . ? C43 C44 C39 119.7(4) . . ? C43 C44 C45 128.2(4) . . ? C39 C44 C45 112.0(4) . . ? C50 C45 C46 106.1(3) . . ? C50 C45 C44 104.2(3) . . ? C46 C45 C44 106.5(3) . . ? C50 C45 H45 113.1 . . ? C46 C45 H45 113.1 . . ? C44 C45 H45 113.1 . . ? C47 C46 C37 119.7(4) . . ? C47 C46 C45 127.6(4) . . ? C37 C46 C45 112.8(4) . . ? C48 C47 C46 119.8(4) . . ? C48 C47 H47 120.1 . . ? C46 C47 H47 120.1 . . ? C47 C48 C35 120.5(4) . . ? C47 C48 H48 119.7 . . ? C35 C48 H48 119.7 . . ? C54 C49 C50 120.1(4) . . ? C54 C49 C38 126.7(4) . . ? C50 C49 C38 113.1(4) . . ? C51 C50 C49 119.8(4) . . ? C51 C50 C45 127.0(4) . . ? C49 C50 C45 113.2(4) . . ? C50 C51 C52 119.8(4) . . ? C50 C51 H51 120.1 . . ? C52 C51 H51 120.1 . . ? C53 C52 C51 120.2(4) . . ? C53 C52 H52 119.9 . . ? C51 C52 H52 119.9 . . ? C52 C53 C54 120.5(4) . . ? C52 C53 H53 119.7 . . ? C54 C53 H53 119.7 . . ? C49 C54 C53 119.6(4) . . ? C49 C54 H54 120.2 . . ? C53 C54 H54 120.2 . . ? O5 C55 C56 134.5(4) . 2_766 ? O5 C55 C56 135.0(4) . . ? C56 C55 C56 90.5(3) 2_766 . ? 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 C8 N1 C1 O1 -2.7(7) . . . . ? C8 N1 C1 C2 174.8(3) . . . . ? C6 N2 C2 C3 0.8(6) . . . . ? C6 N2 C2 C1 -178.2(3) . . . . ? O1 C1 C2 N2 -176.9(4) . . . . ? N1 C1 C2 N2 5.5(5) . . . . ? O1 C1 C2 C3 4.0(6) . . . . ? N1 C1 C2 C3 -173.6(4) . . . . ? N2 C2 C3 C4 -1.3(6) . . . . ? C1 C2 C3 C4 177.7(4) . . . . ? C2 C3 C4 C5 -0.2(6) . . . . ? C3 C4 C5 C6 2.0(6) . . . . ? C2 N2 C6 C5 1.2(6) . . . . ? C2 N2 C6 C7 -178.4(3) . . . . ? C4 C5 C6 N2 -2.7(6) . . . . ? C4 C5 C6 C7 176.9(4) . . . . ? C16 N3 C7 O2 -3.6(7) 2_665 . . . ? C16 N3 C7 C6 175.5(4) 2_665 . . . ? N2 C6 C7 O2 -171.8(4) . . . . ? C5 C6 C7 O2 8.6(6) . . . . ? N2 C6 C7 N3 9.1(6) . . . . ? C5 C6 C7 N3 -170.5(4) . . . . ? C1 N1 C8 C21 -140.8(4) . . . . ? C1 N1 C8 C9 43.5(6) . . . . ? C21 C8 C9 C10 -1.6(6) . . . . ? N1 C8 C9 C10 174.0(4) . . . . ? C8 C9 C10 C11 0.5(6) . . . . ? C9 C10 C11 C20 0.7(6) . . . . ? C9 C10 C11 C12 -177.4(4) . . . . ? C10 C11 C12 C13 123.2(4) . . . . ? C20 C11 C12 C13 -55.0(4) . . . . ? C10 C11 C12 C22 -126.1(4) . . . . ? C20 C11 C12 C22 55.7(4) . . . . ? C22 C12 C13 C14 120.7(4) . . . . ? C11 C12 C13 C14 -127.4(4) . . . . ? C22 C12 C13 C18 -57.5(4) . . . . ? C11 C12 C13 C18 54.3(4) . . . . ? C18 C13 C14 C15 -1.9(6) . . . . ? C12 C13 C14 C15 -180.0(4) . . . . ? C13 C14 C15 C16 -1.2(6) . . . . ? C14 C15 C16 C17 3.2(6) . . . . ? C14 C15 C16 N3 -175.1(4) . . . 2_665 ? C15 C16 C17 C18 -2.0(6) . . . . ? N3 C16 C17 C18 176.4(4) 2_665 . . . ? C16 C17 C18 C13 -1.1(6) . . . . ? C16 C17 C18 C19 178.1(4) . . . . ? C14 C13 C18 C17 3.0(6) . . . . ? C12 C13 C18 C17 -178.6(3) . . . . ? C14 C13 C18 C19 -176.2(3) . . . . ? C12 C13 C18 C19 2.1(5) . . . . ? C17 C18 C19 C20 123.0(4) . . . . ? C13 C18 C19 C20 -57.8(4) . . . . ? C17 C18 C19 C23 -124.6(4) . . . . ? C13 C18 C19 C23 54.6(4) . . . . ? C10 C11 C20 C21 -0.8(6) . . . . ? C12 C11 C20 C21 177.6(3) . . . . ? C10 C11 C20 C19 -179.6(3) . . . . ? C12 C11 C20 C19 -1.2(5) . . . . ? C23 C19 C20 C21 126.9(4) . . . . ? C18 C19 C20 C21 -121.4(4) . . . . ? C23 C19 C20 C11 -54.3(4) . . . . ? C18 C19 C20 C11 57.3(4) . . . . ? C11 C20 C21 C8 -0.4(6) . . . . ? C19 C20 C21 C8 178.3(3) . . . . ? C9 C8 C21 C20 1.6(6) . . . . ? N1 C8 C21 C20 -174.3(3) . . . . ? C13 C12 C22 C27 -119.7(4) . . . . ? C11 C12 C22 C27 128.7(4) . . . . ? C13 C12 C22 C23 56.6(4) . . . . ? C11 C12 C22 C23 -55.0(4) . . . . ? C27 C22 C23 C24 -1.2(6) . . . . ? C12 C22 C23 C24 -177.8(4) . . . . ? C27 C22 C23 C19 176.3(4) . . . . ? C12 C22 C23 C19 -0.3(5) . . . . ? C20 C19 C23 C24 -127.5(4) . . . . ? C18 C19 C23 C24 121.8(4) . . . . ? C20 C19 C23 C22 55.1(4) . . . . ? C18 C19 C23 C22 -55.7(4) . . . . ? C22 C23 C24 C25 1.3(6) . . . . ? C19 C23 C24 C25 -176.0(4) . . . . ? C23 C24 C25 C26 -0.5(7) . . . . ? C24 C25 C26 C27 -0.4(8) . . . . ? C23 C22 C27 C26 0.4(6) . . . . ? C12 C22 C27 C26 176.5(4) . . . . ? C25 C26 C27 C22 0.4(7) . . . . ? C55 C56 C57 C58 1.5(7) 2_766 . . . ? C55 C56 C57 C58 179.8(4) . . . . ? C55 C56 C57 C62 -177.7(4) 2_766 . . . ? C55 C56 C57 C62 0.6(7) . . . . ? C56 C57 C58 C59 -176.9(4) . . . . ? C62 C57 C58 C59 2.3(6) . . . . ? C57 C58 C59 C60 -0.1(6) . . . . ? C65 N7 C60 C61 -8.5(6) . . . . ? C63 N7 C60 C61 165.9(4) . . . . ? C65 N7 C60 C59 173.0(4) . . . . ? C63 N7 C60 C59 -12.6(6) . . . . ? C58 C59 C60 N7 176.1(4) . . . . ? C58 C59 C60 C61 -2.5(6) . . . . ? N7 C60 C61 C62 -175.7(4) . . . . ? C59 C60 C61 C62 2.9(6) . . . . ? C60 C61 C62 C57 -0.7(6) . . . . ? C56 C57 C62 C61 177.4(4) . . . . ? C58 C57 C62 C61 -1.9(6) . . . . ? C60 N7 C63 C64 91.9(5) . . . . ? C65 N7 C63 C64 -93.4(5) . . . . ? C60 N7 C65 C66 87.6(5) . . . . ? C63 N7 C65 C66 -87.1(5) . . . . ? O6 C67 C68 C69 0.1(8) . . . . ? C68 C67 C68 C69 179.6(6) 2_665 . . . ? O6 C67 C68 C67 -179.5(6) . . . 2_665 ? C68 C67 C68 C67 0.0 2_665 . . 2_665 ? C67 C68 C69 C70 175.0(4) 2_665 . . . ? C67 C68 C69 C70 -4.5(7) . . . . ? C67 C68 C69 C74 -5.5(7) 2_665 . . . ? C67 C68 C69 C74 175.0(4) . . . . ? C68 C69 C70 C71 -177.8(4) . . . . ? C74 C69 C70 C71 2.7(6) . . . . ? C69 C70 C71 C72 -1.5(6) . . . . ? C75 N8 C72 C73 171.5(4) . . . . ? C77 N8 C72 C73 -4.5(6) . . . . ? C75 N8 C72 C71 -8.6(6) . . . . ? C77 N8 C72 C71 175.4(4) . . . . ? C70 C71 C72 N8 178.6(4) . . . . ? C70 C71 C72 C73 -1.5(6) . . . . ? N8 C72 C73 C74 -176.8(4) . . . . ? C71 C72 C73 C74 3.3(6) . . . . ? C72 C73 C74 C69 -2.1(6) . . . . ? C70 C69 C74 C73 -0.9(6) . . . . ? C68 C69 C74 C73 179.5(4) . . . . ? C72 N8 C75 C76 86.2(5) . . . . ? C77 N8 C75 C76 -97.6(5) . . . . ? C72 N8 C77 C78 86.7(5) . . . . ? C75 N8 C77 C78 -89.4(5) . . . . ? Cl5 C80 Cl6 Cl6 -153.5(4) . . . 2_756 ? Cl4 C80 Cl6 Cl6 -32.0(7) . . . 2_756 ? C35 N4 C28 O3 4.9(7) . . . . ? C35 N4 C28 C29 -173.8(4) . . . . ? C33 N5 C29 C30 -0.5(6) . . . . ? C33 N5 C29 C28 178.2(4) . . . . ? O3 C28 C29 N5 178.7(4) . . . . ? N4 C28 C29 N5 -2.6(6) . . . . ? O3 C28 C29 C30 -2.5(6) . . . . ? N4 C28 C29 C30 176.2(4) . . . . ? N5 C29 C30 C31 1.0(7) . . . . ? C28 C29 C30 C31 -177.7(4) . . . . ? C29 C30 C31 C32 -0.5(7) . . . . ? C30 C31 C32 C33 -0.4(7) . . . . ? C29 N5 C33 C32 -0.5(6) . . . . ? C29 N5 C33 C34 177.9(4) . . . . ? C31 C32 C33 N5 0.9(7) . . . . ? C31 C32 C33 C34 -177.4(4) . . . . ? C41 N6 C34 O4 2.4(7) 2_766 . . . ? C41 N6 C34 C33 -176.2(4) 2_766 . . . ? N5 C33 C34 O4 -176.8(4) . . . . ? C32 C33 C34 O4 1.7(6) . . . . ? N5 C33 C34 N6 1.9(5) . . . . ? C32 C33 C34 N6 -179.6(4) . . . . ? C28 N4 C35 C48 -43.8(6) . . . . ? C28 N4 C35 C36 138.7(4) . . . . ? C48 C35 C36 C37 -2.7(6) . . . . ? N4 C35 C36 C37 174.9(4) . . . . ? C35 C36 C37 C46 -2.2(6) . . . . ? C35 C36 C37 C38 179.7(4) . . . . ? C36 C37 C38 C39 120.3(4) . . . . ? C46 C37 C38 C39 -57.8(4) . . . . ? C36 C37 C38 C49 -128.8(4) . . . . ? C46 C37 C38 C49 53.0(4) . . . . ? C37 C38 C39 C40 -123.1(4) . . . . ? C49 C38 C39 C40 124.6(4) . . . . ? C37 C38 C39 C44 56.2(4) . . . . ? C49 C38 C39 C44 -56.1(4) . . . . ? C44 C39 C40 C41 2.1(6) . . . . ? C38 C39 C40 C41 -178.7(4) . . . . ? C39 C40 C41 C42 -0.2(6) . . . . ? C39 C40 C41 N6 -175.6(4) . . . 2_766 ? C40 C41 C42 C43 -0.7(6) . . . . ? N6 C41 C42 C43 174.4(4) 2_766 . . . ? C41 C42 C43 C44 -0.2(6) . . . . ? C42 C43 C44 C39 2.1(7) . . . . ? C42 C43 C44 C45 179.7(4) . . . . ? C40 C39 C44 C43 -3.1(6) . . . . ? C38 C39 C44 C43 177.6(4) . . . . ? C40 C39 C44 C45 178.9(4) . . . . ? C38 C39 C44 C45 -0.4(5) . . . . ? C43 C44 C45 C50 -120.7(5) . . . . ? C39 C44 C45 C50 57.1(4) . . . . ? C43 C44 C45 C46 127.4(5) . . . . ? C39 C44 C45 C46 -54.8(4) . . . . ? C36 C37 C46 C47 5.5(6) . . . . ? C38 C37 C46 C47 -176.2(4) . . . . ? C36 C37 C46 C45 -175.4(4) . . . . ? C38 C37 C46 C45 2.9(5) . . . . ? C50 C45 C46 C47 121.8(5) . . . . ? C44 C45 C46 C47 -127.6(4) . . . . ? C50 C45 C46 C37 -57.2(4) . . . . ? C44 C45 C46 C37 53.4(4) . . . . ? C37 C46 C47 C48 -3.8(6) . . . . ? C45 C46 C47 C48 177.3(4) . . . . ? C46 C47 C48 C35 -1.1(6) . . . . ? N4 C35 C48 C47 -173.0(4) . . . . ? C36 C35 C48 C47 4.4(6) . . . . ? C39 C38 C49 C54 -121.3(5) . . . . ? C37 C38 C49 C54 127.5(5) . . . . ? C39 C38 C49 C50 55.9(5) . . . . ? C37 C38 C49 C50 -55.3(5) . . . . ? C54 C49 C50 C51 0.1(7) . . . . ? C38 C49 C50 C51 -177.3(4) . . . . ? C54 C49 C50 C45 178.5(4) . . . . ? C38 C49 C50 C45 1.1(5) . . . . ? C46 C45 C50 C51 -127.0(5) . . . . ? C44 C45 C50 C51 120.8(5) . . . . ? C46 C45 C50 C49 54.8(5) . . . . ? C44 C45 C50 C49 -57.4(5) . . . . ? C49 C50 C51 C52 1.1(7) . . . . ? C45 C50 C51 C52 -177.1(5) . . . . ? C50 C51 C52 C53 -0.8(8) . . . . ? C51 C52 C53 C54 -0.7(8) . . . . ? C50 C49 C54 C53 -1.5(7) . . . . ? C38 C49 C54 C53 175.5(4) . . . . ? C52 C53 C54 C49 1.8(7) . . . . ? C57 C56 C55 O5 2.5(8) . . . . ? C55 C56 C55 O5 -178.6(6) 2_766 . . . ? C57 C56 C55 C56 -178.8(6) . . . 2_766 ? C55 C56 C55 C56 0.0 2_766 . . 2_766 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.791 _refine_diff_density_min -0.749 _refine_diff_density_rms 0.078 # Attachment '2.cif' data_r80516e _database_code_depnum_ccdc_archive 'CCDC 697890' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C54 H34 N6 O4' _chemical_formula_sum 'C54 H34 N6 O4' _chemical_formula_weight 830.87 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 28.750(6) _cell_length_b 11.657(2) _cell_length_c 14.303(3) _cell_angle_alpha 90.00 _cell_angle_beta 99.60(3) _cell_angle_gamma 90.00 _cell_volume 4726.5(16) _cell_formula_units_Z 4 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 5183 _cell_measurement_theta_min 1.859 _cell_measurement_theta_max 27.487 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.168 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1728 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9895 _exptl_absorpt_correction_T_max 0.9940 _exptl_absorpt_process_details crystalclear _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type 'rigaku saturn CCD area detector' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean 7.31 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 16512 _diffrn_reflns_av_R_equivalents 0.0596 _diffrn_reflns_av_sigmaI/netI 0.0843 _diffrn_reflns_limit_h_min -37 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 27.55 _reflns_number_total 5437 _reflns_number_gt 3788 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'crystalclear(Rigaku/MSC Inc., 2005)' _computing_cell_refinement crystalclear _computing_data_reduction crystalclear _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^)+(0.1096P)^2^+1.4838P] 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 SHELXL _refine_ls_extinction_coef 0.0041(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5437 _refine_ls_number_parameters 290 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0950 _refine_ls_R_factor_gt 0.0699 _refine_ls_wR_factor_ref 0.2036 _refine_ls_wR_factor_gt 0.1853 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 O1 O 0.27749(7) 0.8743(2) 0.02964(13) 0.0658(7) Uani 1 1 d . . . O2 O 0.04006(5) 0.88904(14) 0.65430(11) 0.0363(4) Uani 1 1 d . . . N1 N 0.26765(7) 0.78633(19) 0.16717(14) 0.0416(5) Uani 1 1 d . . . H1 H 0.2834 0.7526 0.2158 0.050 Uiso 1 1 calc R . . N2 N 0.10515(7) 0.80825(16) 0.60960(12) 0.0318(4) Uani 1 1 d . . . H2 H 0.1324 0.7808 0.6325 0.038 Uiso 1 1 calc R . . N3 N 0.14083(6) 0.76120(16) 0.79180(12) 0.0310(4) Uani 1 1 d . . . C1 C 0.29305(9) 0.8197(2) 0.10223(16) 0.0435(6) Uani 1 1 d . . . C2 C 0.21904(8) 0.7977(2) 0.16859(16) 0.0356(5) Uani 1 1 d . . . C3 C 0.19146(8) 0.8844(2) 0.11985(16) 0.0397(6) Uani 1 1 d . . . H3 H 0.2047 0.9362 0.0824 0.048 Uiso 1 1 calc R . . C4 C 0.14367(8) 0.8924(2) 0.12806(16) 0.0353(5) Uani 1 1 d . . . H4 H 0.1250 0.9490 0.0949 0.042 Uiso 1 1 calc R . . C5 C 0.12416(8) 0.81709(19) 0.18475(14) 0.0292(5) Uani 1 1 d . . . C6 C 0.15234(8) 0.73063(18) 0.23316(14) 0.0296(5) Uani 1 1 d . . . C7 C 0.19915(8) 0.7207(2) 0.22497(15) 0.0328(5) Uani 1 1 d . . . H7 H 0.2175 0.6626 0.2570 0.039 Uiso 1 1 calc R . . C8 C 0.12626(8) 0.65576(18) 0.29426(14) 0.0297(5) Uani 1 1 d . . . H8 H 0.1461 0.5957 0.3282 0.036 Uiso 1 1 calc R . . C9 C 0.08347(8) 0.60873(18) 0.22838(14) 0.0298(5) Uani 1 1 d . . . C10 C 0.07158(8) 0.4949(2) 0.21560(16) 0.0368(5) Uani 1 1 d . . . H10 H 0.0911 0.4385 0.2471 0.044 Uiso 1 1 calc R . . C11 C 0.02990(9) 0.4639(2) 0.15485(16) 0.0391(6) Uani 1 1 d . . . H11 H 0.0215 0.3871 0.1457 0.047 Uiso 1 1 calc R . . C12 C 0.00148(9) 0.5499(2) 0.10871(16) 0.0382(5) Uani 1 1 d . . . H12 H -0.0265 0.5305 0.0692 0.046 Uiso 1 1 calc R . . C13 C 0.01425(7) 0.66470(19) 0.12083(14) 0.0283(5) Uani 1 1 d . . . H13 H -0.0048 0.7213 0.0885 0.034 Uiso 1 1 calc R . . C14 C 0.05488(8) 0.69449(18) 0.18043(14) 0.0286(5) Uani 1 1 d . . . C15 C 0.07381(8) 0.81526(18) 0.20428(14) 0.0292(5) Uani 1 1 d . . . H15 H 0.0540 0.8753 0.1702 0.035 Uiso 1 1 calc R . . C16 C 0.07840(7) 0.82532(18) 0.31221(14) 0.0276(4) Uani 1 1 d . . . C17 C 0.05843(7) 0.90670(17) 0.36273(14) 0.0284(5) Uani 1 1 d . . . H17 H 0.0396 0.9641 0.3309 0.034 Uiso 1 1 calc R . . C18 C 0.06632(8) 0.90337(18) 0.46246(14) 0.0304(5) Uani 1 1 d . . . H18 H 0.0528 0.9583 0.4968 0.037 Uiso 1 1 calc R . . C19 C 0.09448(8) 0.81714(19) 0.50916(14) 0.0297(5) Uani 1 1 d . . . C20 C 0.11442(8) 0.73435(18) 0.45777(14) 0.0295(5) Uani 1 1 d . . . H20 H 0.1329 0.6761 0.4892 0.035 Uiso 1 1 calc R . . C21 C 0.10664(8) 0.73930(18) 0.36027(14) 0.0282(5) Uani 1 1 d . . . C22 C 0.07759(8) 0.83776(18) 0.67305(14) 0.0278(5) Uani 1 1 d . . . C23 C 0.09574(8) 0.79610(18) 0.77254(14) 0.0283(5) Uani 1 1 d . . . C24 C 0.06533(8) 0.79043(19) 0.83794(15) 0.0328(5) Uani 1 1 d . . . H24 H 0.0347 0.8186 0.8234 0.039 Uiso 1 1 calc R . . C25 C 0.08165(9) 0.7419(2) 0.92531(15) 0.0370(5) Uani 1 1 d . . . H25 H 0.0618 0.7352 0.9701 0.044 Uiso 1 1 calc R . . C26 C 0.12775(9) 0.7032(2) 0.94583(16) 0.0388(6) Uani 1 1 d . . . H26 H 0.1392 0.6692 1.0039 0.047 Uiso 1 1 calc R . . C27 C 0.15623(8) 0.7164(2) 0.87786(15) 0.0356(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0419(11) 0.1120(18) 0.0444(10) 0.0375(11) 0.0096(9) 0.0179(11) O2 0.0300(9) 0.0422(9) 0.0374(8) 0.0053(7) 0.0077(7) 0.0068(7) N1 0.0277(11) 0.0646(14) 0.0314(10) 0.0129(9) 0.0016(8) 0.0076(9) N2 0.0295(10) 0.0381(10) 0.0260(9) -0.0012(7) -0.0008(8) 0.0028(8) N3 0.0271(10) 0.0371(10) 0.0280(9) 0.0002(7) 0.0026(7) -0.0020(8) C1 0.0375(14) 0.0641(17) 0.0287(11) 0.0086(11) 0.0049(10) 0.0027(12) C2 0.0267(12) 0.0472(13) 0.0325(11) 0.0040(9) 0.0033(9) 0.0006(10) C3 0.0315(13) 0.0524(15) 0.0344(11) 0.0125(10) 0.0032(10) 0.0007(10) C4 0.0279(12) 0.0427(13) 0.0327(11) 0.0074(9) -0.0030(9) 0.0009(9) C5 0.0271(12) 0.0384(12) 0.0208(9) 0.0013(8) -0.0004(8) 0.0034(9) C6 0.0287(12) 0.0322(11) 0.0262(10) -0.0005(8) -0.0008(8) 0.0015(9) C7 0.0299(12) 0.0394(12) 0.0276(10) 0.0022(8) 0.0000(9) 0.0064(9) C8 0.0314(12) 0.0303(11) 0.0268(10) 0.0014(8) 0.0028(9) 0.0046(8) C9 0.0300(12) 0.0311(11) 0.0278(10) -0.0013(8) 0.0033(8) 0.0030(8) C10 0.0404(14) 0.0336(12) 0.0360(11) -0.0034(9) 0.0051(10) -0.0001(10) C11 0.0377(14) 0.0410(13) 0.0390(12) -0.0037(10) 0.0073(10) -0.0021(10) C12 0.0332(13) 0.0498(14) 0.0312(11) -0.0072(10) 0.0046(10) -0.0051(10) C13 0.0282(12) 0.0344(11) 0.0229(9) -0.0020(8) 0.0056(8) 0.0026(8) C14 0.0296(12) 0.0330(11) 0.0241(9) -0.0004(8) 0.0069(8) 0.0013(8) C15 0.0287(12) 0.0311(11) 0.0261(10) 0.0031(8) -0.0004(8) 0.0017(8) C16 0.0214(11) 0.0313(11) 0.0286(10) 0.0013(8) -0.0003(8) -0.0018(8) C17 0.0266(11) 0.0261(10) 0.0305(10) 0.0028(8) -0.0014(8) 0.0026(8) C18 0.0307(12) 0.0292(11) 0.0301(10) -0.0057(8) 0.0014(9) 0.0001(8) C19 0.0277(12) 0.0343(11) 0.0256(10) -0.0018(8) 0.0002(9) 0.0000(8) C20 0.0276(11) 0.0313(11) 0.0282(10) 0.0013(8) 0.0004(9) 0.0022(8) C21 0.0274(11) 0.0279(10) 0.0280(10) 0.0008(8) 0.0004(8) -0.0019(8) C22 0.0289(12) 0.0269(10) 0.0274(10) -0.0023(8) 0.0041(8) -0.0024(8) C23 0.0281(12) 0.0295(11) 0.0269(10) -0.0025(8) 0.0036(8) -0.0033(8) C24 0.0291(12) 0.0375(12) 0.0322(11) -0.0048(9) 0.0060(9) -0.0015(9) C25 0.0353(13) 0.0489(14) 0.0289(11) -0.0053(9) 0.0116(10) -0.0039(10) C26 0.0365(14) 0.0545(15) 0.0255(10) 0.0021(9) 0.0060(10) -0.0016(11) C27 0.0320(13) 0.0482(14) 0.0255(10) 0.0026(9) 0.0017(9) -0.0011(10) _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 O1 C1 1.236(3) . ? O2 C22 1.224(3) . ? N1 C1 1.331(3) . ? N1 C2 1.407(3) . ? N1 H1 0.8600 . ? N2 C22 1.345(3) . ? N2 C19 1.422(3) . ? N2 H2 0.8600 . ? N3 C27 1.343(3) . ? N3 C23 1.343(3) . ? C1 C27 1.498(4) 7_566 ? C2 C7 1.392(3) . ? C2 C3 1.397(3) . ? C3 C4 1.402(3) . ? C3 H3 0.9300 . ? C4 C5 1.376(3) . ? C4 H4 0.9300 . ? C5 C6 1.402(3) . ? C5 C15 1.519(3) . ? C6 C7 1.375(3) . ? C6 C8 1.519(3) . ? C7 H7 0.9300 . ? C8 C9 1.521(3) . ? C8 C21 1.528(3) . ? C8 H8 0.9800 . ? C9 C10 1.375(3) . ? C9 C14 1.399(3) . ? C10 C11 1.405(3) . ? C10 H10 0.9300 . ? C11 C12 1.389(3) . ? C11 H11 0.9300 . ? C12 C13 1.391(3) . ? C12 H12 0.9300 . ? C13 C14 1.371(3) . ? C13 H13 0.9300 . ? C14 C15 1.527(3) . ? C15 C16 1.532(3) . ? C15 H15 0.9800 . ? C16 C17 1.375(3) . ? C16 C21 1.397(3) . ? C17 C18 1.407(3) . ? C17 H17 0.9300 . ? C18 C19 1.390(3) . ? C18 H18 0.9300 . ? C19 C20 1.393(3) . ? C20 C21 1.376(3) . ? C20 H20 0.9300 . ? C22 C23 1.512(3) . ? C23 C24 1.384(3) . ? C24 C25 1.381(3) . ? C24 H24 0.9300 . ? C25 C26 1.384(3) . ? C25 H25 0.9300 . ? C26 C27 1.380(3) . ? C26 H26 0.9300 . ? C27 C1 1.498(4) 7_566 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C2 130.1(2) . . ? C1 N1 H1 115.0 . . ? C2 N1 H1 115.0 . . ? C22 N2 C19 127.66(19) . . ? C22 N2 H2 116.2 . . ? C19 N2 H2 116.2 . . ? C27 N3 C23 117.75(19) . . ? O1 C1 N1 124.9(2) . . ? O1 C1 C27 120.5(2) . 7_566 ? N1 C1 C27 114.5(2) . 7_566 ? C7 C2 C3 120.1(2) . . ? C7 C2 N1 116.9(2) . . ? C3 C2 N1 122.9(2) . . ? C2 C3 C4 119.3(2) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C5 C4 C3 120.6(2) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C4 C5 C6 119.4(2) . . ? C4 C5 C15 127.70(19) . . ? C6 C5 C15 112.89(19) . . ? C7 C6 C5 120.8(2) . . ? C7 C6 C8 125.78(19) . . ? C5 C6 C8 113.41(19) . . ? C6 C7 C2 119.8(2) . . ? C6 C7 H7 120.1 . . ? C2 C7 H7 120.1 . . ? C6 C8 C9 106.05(16) . . ? C6 C8 C21 104.95(17) . . ? C9 C8 C21 105.58(17) . . ? C6 C8 H8 113.2 . . ? C9 C8 H8 113.2 . . ? C21 C8 H8 113.2 . . ? C10 C9 C14 120.8(2) . . ? C10 C9 C8 126.0(2) . . ? C14 C9 C8 113.23(18) . . ? C9 C10 C11 119.9(2) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? C12 C11 C10 118.8(2) . . ? C12 C11 H11 120.6 . . ? C10 C11 H11 120.6 . . ? C11 C12 C13 120.9(2) . . ? C11 C12 H12 119.5 . . ? C13 C12 H12 119.5 . . ? C14 C13 C12 120.1(2) . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C13 C14 C9 119.6(2) . . ? C13 C14 C15 127.39(19) . . ? C9 C14 C15 113.00(18) . . ? C5 C15 C14 106.66(17) . . ? C5 C15 C16 105.05(16) . . ? C14 C15 C16 105.26(16) . . ? C5 C15 H15 113.1 . . ? C14 C15 H15 113.1 . . ? C16 C15 H15 113.1 . . ? C17 C16 C21 119.74(19) . . ? C17 C16 C15 127.53(19) . . ? C21 C16 C15 112.73(18) . . ? C16 C17 C18 120.19(19) . . ? C16 C17 H17 119.9 . . ? C18 C17 H17 119.9 . . ? C19 C18 C17 119.32(19) . . ? C19 C18 H18 120.3 . . ? C17 C18 H18 120.3 . . ? C18 C19 C20 120.37(19) . . ? C18 C19 N2 123.26(19) . . ? C20 C19 N2 116.37(19) . . ? C21 C20 C19 119.59(19) . . ? C21 C20 H20 120.2 . . ? C19 C20 H20 120.2 . . ? C20 C21 C16 120.8(2) . . ? C20 C21 C8 125.80(19) . . ? C16 C21 C8 113.42(18) . . ? O2 C22 N2 125.05(19) . . ? O2 C22 C23 121.09(19) . . ? N2 C22 C23 113.79(18) . . ? N3 C23 C24 122.9(2) . . ? N3 C23 C22 117.40(18) . . ? C24 C23 C22 119.6(2) . . ? C25 C24 C23 118.3(2) . . ? C25 C24 H24 120.9 . . ? C23 C24 H24 120.9 . . ? C24 C25 C26 119.6(2) . . ? C24 C25 H25 120.2 . . ? C26 C25 H25 120.2 . . ? C27 C26 C25 118.3(2) . . ? C27 C26 H26 120.9 . . ? C25 C26 H26 120.9 . . ? N3 C27 C26 123.0(2) . . ? N3 C27 C1 116.4(2) . 7_566 ? C26 C27 C1 120.5(2) . 7_566 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 N1 C1 O1 3.7(5) . . . . ? C2 N1 C1 C27 -175.2(2) . . . 7_566 ? C1 N1 C2 C7 156.8(3) . . . . ? C1 N1 C2 C3 -25.9(4) . . . . ? C7 C2 C3 C4 -0.3(4) . . . . ? N1 C2 C3 C4 -177.5(2) . . . . ? C2 C3 C4 C5 1.1(4) . . . . ? C3 C4 C5 C6 -1.1(3) . . . . ? C3 C4 C5 C15 178.0(2) . . . . ? C4 C5 C6 C7 0.3(3) . . . . ? C15 C5 C6 C7 -178.94(19) . . . . ? C4 C5 C6 C8 178.89(19) . . . . ? C15 C5 C6 C8 -0.4(3) . . . . ? C5 C6 C7 C2 0.5(3) . . . . ? C8 C6 C7 C2 -177.9(2) . . . . ? C3 C2 C7 C6 -0.5(3) . . . . ? N1 C2 C7 C6 176.8(2) . . . . ? C7 C6 C8 C9 -125.9(2) . . . . ? C5 C6 C8 C9 55.6(2) . . . . ? C7 C6 C8 C21 122.7(2) . . . . ? C5 C6 C8 C21 -55.8(2) . . . . ? C6 C8 C9 C10 125.5(2) . . . . ? C21 C8 C9 C10 -123.5(2) . . . . ? C6 C8 C9 C14 -55.9(2) . . . . ? C21 C8 C9 C14 55.2(2) . . . . ? C14 C9 C10 C11 -1.0(3) . . . . ? C8 C9 C10 C11 177.6(2) . . . . ? C9 C10 C11 C12 0.0(3) . . . . ? C10 C11 C12 C13 1.1(3) . . . . ? C11 C12 C13 C14 -1.3(3) . . . . ? C12 C13 C14 C9 0.4(3) . . . . ? C12 C13 C14 C15 -178.4(2) . . . . ? C10 C9 C14 C13 0.8(3) . . . . ? C8 C9 C14 C13 -177.98(18) . . . . ? C10 C9 C14 C15 179.69(19) . . . . ? C8 C9 C14 C15 1.0(2) . . . . ? C4 C5 C15 C14 126.0(2) . . . . ? C6 C5 C15 C14 -54.8(2) . . . . ? C4 C5 C15 C16 -122.5(2) . . . . ? C6 C5 C15 C16 56.6(2) . . . . ? C13 C14 C15 C5 -126.6(2) . . . . ? C9 C14 C15 C5 54.5(2) . . . . ? C13 C14 C15 C16 122.1(2) . . . . ? C9 C14 C15 C16 -56.7(2) . . . . ? C5 C15 C16 C17 123.5(2) . . . . ? C14 C15 C16 C17 -124.1(2) . . . . ? C5 C15 C16 C21 -56.4(2) . . . . ? C14 C15 C16 C21 56.0(2) . . . . ? C21 C16 C17 C18 -0.1(3) . . . . ? C15 C16 C17 C18 -180.0(2) . . . . ? C16 C17 C18 C19 0.0(3) . . . . ? C17 C18 C19 C20 -0.4(3) . . . . ? C17 C18 C19 N2 178.7(2) . . . . ? C22 N2 C19 C18 32.7(3) . . . . ? C22 N2 C19 C20 -148.1(2) . . . . ? C18 C19 C20 C21 0.9(3) . . . . ? N2 C19 C20 C21 -178.32(19) . . . . ? C19 C20 C21 C16 -1.0(3) . . . . ? C19 C20 C21 C8 179.5(2) . . . . ? C17 C16 C21 C20 0.5(3) . . . . ? C15 C16 C21 C20 -179.52(19) . . . . ? C17 C16 C21 C8 -179.90(19) . . . . ? C15 C16 C21 C8 0.0(3) . . . . ? C6 C8 C21 C20 -124.5(2) . . . . ? C9 C8 C21 C20 123.7(2) . . . . ? C6 C8 C21 C16 56.0(2) . . . . ? C9 C8 C21 C16 -55.8(2) . . . . ? C19 N2 C22 O2 -8.2(4) . . . . ? C19 N2 C22 C23 168.75(19) . . . . ? C27 N3 C23 C24 1.7(3) . . . . ? C27 N3 C23 C22 -175.30(19) . . . . ? O2 C22 C23 N3 -167.2(2) . . . . ? N2 C22 C23 N3 15.8(3) . . . . ? O2 C22 C23 C24 15.7(3) . . . . ? N2 C22 C23 C24 -161.3(2) . . . . ? N3 C23 C24 C25 -3.0(3) . . . . ? C22 C23 C24 C25 173.92(19) . . . . ? C23 C24 C25 C26 1.6(3) . . . . ? C24 C25 C26 C27 1.0(4) . . . . ? C23 N3 C27 C26 1.1(3) . . . . ? C23 N3 C27 C1 -178.9(2) . . . 7_566 ? C25 C26 C27 N3 -2.4(4) . . . . ? C25 C26 C27 C1 177.6(2) . . . 7_566 ? _publ_section_exptl_refinement ; The solvent molecules are disordered strongly and are taken out by SQUEEZE. ; loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons 1 0.250 -0.250 0.500 246.5 46.1 2 0.250 0.250 1.000 246.5 46.1 3 0.750 -0.250 0.000 246.4 46.1 4 0.750 0.250 0.500 246.5 46.1 _platon_squeeze_details ; ; _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.55 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.613 _refine_diff_density_min -0.215 _refine_diff_density_rms 0.062