Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'A W Coleman' _publ_contact_author_email AW.COLEMAN@IBCP.FR _publ_section_title ; Solid State Structures of the Complexes Between the Antiseptic Chlorhexidine and Three Anionic Derivatives of Calix[4]arene ; loop_ _publ_author_name 'A W Coleman' 'Oksana Danylyuk' 'Nathalie Dupont' 'Adina Lazar' 'Alda Navaza' 'Florent Perret' ; K.Suwinska ; # Attachment 'C4S-chorhex.cif' data_Calix[4]sulfonateChlorhexidine _database_code_depnum_ccdc_archive 'CCDC 661947' _audit_creation_method SHELXL-97 # PROCESSING SUMMARY (IUCr Office Use Only) # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; 'para-sulfonatocalix[4]arene Chlorhexidine' ; _chemical_formula_sum 'C53 H77 Cl2 N10 O25 S4' _chemical_formula_moiety ' C22 H33 Cl2 N10, C28 H20 O16 S4,3(C1 H4 O1), 6(H2 O1) ' _chemical_formula_weight 1453.39 _chemical_absolute_configuration syn #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' _cell_length_a 15.3260(5) _cell_length_b 15.9820(5) _cell_length_c 16.1350(4) _cell_angle_alpha 65.687(2) _cell_angle_beta 77.180(2) _cell_angle_gamma 64.4270(10) _cell_volume 3244.08(17) _cell_formula_units_Z 2 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 9255 _cell_measurement_theta_min 2.95 _cell_measurement_theta_max 23.26 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description parallepiped _exptl_crystal_colour colorless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_crystal_density_diffrn 1.488 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1526 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.318 _exptl_absorpt_correction_type sphere #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method rotation _diffrn_detector_area_resol_mean 9.1 _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.0432 _diffrn_reflns_av_unetI/netI 0.0663 _diffrn_reflns_number 17554 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.95 _diffrn_reflns_theta_max 23.26 _diffrn_reflns_theta_full 23.26 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _reflns_number_total 9255 _reflns_number_gt 6813 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect data collection software (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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.Restraints were used to fix solvent geometries : distances and angles. ; _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^)+(0.0691P)^2^+3.8457P] 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_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.0028(5) _refine_ls_number_reflns 9255 _refine_ls_number_parameters 830 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.0803 _refine_ls_R_factor_gt 0.0544 _refine_ls_wR_factor_ref 0.1433 _refine_ls_wR_factor_gt 0.1313 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.816 _refine_diff_density_min -0.429 _refine_diff_density_rms 0.074 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 O1W O 0.3441(2) 0.7257(2) 0.92981(18) 0.0257(7) Uani 1 1 d D . . O2W O 0.6137(2) 0.5195(2) 0.4332(2) 0.0314(8) Uani 1 1 d D . . O3W O 0.2268(2) 0.0941(2) 0.7165(2) 0.0310(8) Uani 1 1 d D . . O4W O 0.6500(2) 0.7410(3) 0.7485(2) 0.0397(8) Uani 1 1 d D . . O5W O 0.2175(3) 0.1911(3) 0.3790(2) 0.0422(9) Uani 1 1 d D . . O6W O 0.4447(3) 0.2347(3) 0.0276(2) 0.0449(9) Uani 1 1 d D . . H1W1 H 0.350(4) 0.673(2) 0.976(2) 0.054 Uiso 1 1 d D . . H2W1 H 0.346(4) 0.770(3) 0.942(3) 0.054 Uiso 1 1 d D . . H1W2 H 0.604(4) 0.467(2) 0.466(3) 0.054 Uiso 1 1 d D . . H2W2 H 0.573(3) 0.570(2) 0.446(3) 0.054 Uiso 1 1 d D . . H1W3 H 0.235(4) 0.148(2) 0.682(2) 0.054 Uiso 1 1 d D . . H2W3 H 0.230(4) 0.089(4) 0.7707(15) 0.054 Uiso 1 1 d D . . H1W4 H 0.613(3) 0.736(4) 0.723(3) 0.054 Uiso 1 1 d D . . H2W4 H 0.667(4) 0.701(3) 0.8017(18) 0.054 Uiso 1 1 d D . . H1W5 H 0.252(3) 0.130(2) 0.380(3) 0.054 Uiso 1 1 d D . . H2W5 H 0.235(4) 0.197(3) 0.422(3) 0.054 Uiso 1 1 d D . . H1W6 H 0.414(3) 0.288(2) 0.041(3) 0.054 Uiso 1 1 d D . . H2W6 H 0.461(4) 0.186(2) 0.079(2) 0.054 Uiso 1 1 d D . . Cl1 Cl 0.98586(7) 0.84075(8) 0.62544(7) 0.0258(3) Uani 1 1 d . . . C1 C 1.0837(3) 0.8574(3) 0.6448(3) 0.0206(9) Uani 1 1 d . . . C2 C 1.1106(3) 0.9328(3) 0.5814(3) 0.0250(10) Uani 1 1 d . . . H2 H 1.0789 0.9729 0.5258 0.03 Uiso 1 1 calc R . . C3 C 1.1845(3) 0.9494(3) 0.5999(3) 0.0221(10) Uani 1 1 d . . . H3 H 1.2035 1.0015 0.5569 0.027 Uiso 1 1 calc R . . C4 C 1.2307(3) 0.8906(3) 0.6807(3) 0.0190(9) Uani 1 1 d . . . C5 C 1.2042(3) 0.8140(3) 0.7432(3) 0.0224(10) Uani 1 1 d . . . H5 H 1.2366 0.7731 0.7983 0.027 Uiso 1 1 calc R . . C6 C 1.1298(3) 0.7969(3) 0.7254(3) 0.0232(10) Uani 1 1 d . . . H6 H 1.1111 0.7445 0.7679 0.028 Uiso 1 1 calc R . . N7 N 1.3041(2) 0.9123(2) 0.7003(2) 0.0215(8) Uani 1 1 d . . . H7A H 1.3083 0.967 0.6517 0.026 Uiso 0.5 1 calc PR . . H7B H 1.2801 0.9321 0.7496 0.026 Uiso 0.5 1 calc PR . . C8 C 1.3945(3) 0.8471(3) 0.7176(2) 0.0173(9) Uani 1 1 d . . . N8 N 1.4504(2) 0.8599(2) 0.7579(2) 0.0230(8) Uani 1 1 d . . . H8A H 1.4283 0.9121 0.774 0.028 Uiso 1 1 calc R . . H8B H 1.5101 0.8163 0.769 0.028 Uiso 1 1 calc R . . N9 N 1.4296(2) 0.7681(2) 0.6890(2) 0.0178(8) Uani 1 1 d . . . H9A H 1.4521 0.7904 0.6295 0.021 Uiso 0.5 1 calc PR . . H9B H 1.3769 0.7553 0.6878 0.021 Uiso 0.5 1 calc PR . . C10 C 1.5011(3) 0.6764(3) 0.7323(3) 0.0165(9) Uani 1 1 d . . . N10 N 1.4996(2) 0.6414(2) 0.8224(2) 0.0200(8) Uani 1 1 d . . . H10A H 1.5413 0.582 0.8516 0.024 Uiso 1 1 calc R . . H10B H 1.4568 0.6776 0.8531 0.024 Uiso 1 1 calc R . . N11 N 1.5610(2) 0.6294(2) 0.6804(2) 0.0174(8) Uani 1 1 d . . . H11A H 1.5924 0.6699 0.6413 0.021 Uiso 1 1 calc R . . C12 C 1.6362(3) 0.5292(3) 0.7156(3) 0.0213(10) Uani 1 1 d . . . H12A H 1.624 0.4989 0.782 0.026 Uiso 1 1 calc R . . H12B H 1.7004 0.5336 0.7051 0.026 Uiso 1 1 calc R . . C13 C 1.6360(3) 0.4643(3) 0.6685(3) 0.0205(9) Uani 1 1 d . . . H13A H 1.649 0.4944 0.6022 0.025 Uiso 1 1 calc R . . H13B H 1.5713 0.4611 0.6782 0.025 Uiso 1 1 calc R . . C14 C 1.7128(3) 0.3590(3) 0.7053(3) 0.0232(10) Uani 1 1 d . . . H14A H 1.7775 0.3629 0.6911 0.028 Uiso 1 1 calc R . . H14B H 1.7103 0.3193 0.673 0.028 Uiso 1 1 calc R . . C15 C 1.7017(3) 0.3044(3) 0.8082(3) 0.0221(10) Uani 1 1 d . . . H15A H 1.7501 0.2353 0.824 0.026 Uiso 1 1 calc R . . H15B H 1.717 0.3369 0.8405 0.026 Uiso 1 1 calc R . . C16 C 1.6020(3) 0.3011(3) 0.8433(3) 0.0228(10) Uani 1 1 d . . . H16A H 1.6033 0.2624 0.9095 0.027 Uiso 1 1 calc R . . H16B H 1.5543 0.3697 0.8343 0.027 Uiso 1 1 calc R . . C17 C 1.5687(3) 0.2556(3) 0.7968(3) 0.0212(10) Uani 1 1 d . . . H17A H 1.5574 0.2994 0.7322 0.025 Uiso 1 1 calc R . . H17B H 1.6198 0.1904 0.7984 0.025 Uiso 1 1 calc R . . N18 N 1.4793(2) 0.2424(3) 0.8427(2) 0.0239(8) Uani 1 1 d . . . H18A H 1.4976 0.1845 0.8926 0.029 Uiso 0.5 1 calc PR . . H18B H 1.4463 0.2932 0.8649 0.029 Uiso 0.5 1 calc PR . . C19 C 1.4158(3) 0.2386(3) 0.8035(3) 0.0215(10) Uani 1 1 d . . . N19 N 1.4282(3) 0.2365(3) 0.7215(2) 0.0311(9) Uani 1 1 d . . . H19A H 1.4821 0.2377 0.6888 0.037 Uiso 1 1 calc R . . H19B H 1.3825 0.234 0.6989 0.037 Uiso 1 1 calc R . . N20 N 1.3287(2) 0.2349(3) 0.8503(2) 0.0265(9) Uani 1 1 d . . . H20B H 1.3399 0.1686 0.8811 0.032 Uiso 1 1 calc R . . C21 C 1.2790(3) 0.2815(3) 0.9112(3) 0.0232(10) Uani 1 1 d . . . N21 N 1.2775(3) 0.3674(3) 0.8976(2) 0.0273(9) Uani 1 1 d . . . H21A H 1.2436 0.3984 0.9354 0.033 Uiso 1 1 calc R . . N22 N 1.2315(3) 0.2339(3) 0.9805(3) 0.0404(11) Uani 1 1 d . . . H22B H 1.2043 0.2078 0.9568 0.048 Uiso 1 1 calc R . . C23 C 1.1569(3) 0.2810(3) 1.0368(3) 0.0314(12) Uani 1 1 d . . . C24 C 1.0665(4) 0.3459(4) 1.0031(3) 0.0362(12) Uani 1 1 d . . . H24 H 1.0543 0.3591 0.9428 0.043 Uiso 1 1 calc R . . C25 C 0.9938(3) 0.3915(4) 1.0568(3) 0.0326(11) Uani 1 1 d . . . H25 H 0.9319 0.4368 1.0339 0.039 Uiso 1 1 calc R . . C26 C 1.0134(3) 0.3698(3) 1.1439(3) 0.0247(10) Uani 1 1 d . . . Cl26 Cl 0.92069(8) 0.42886(8) 1.21034(7) 0.0303(3) Uani 1 1 d . . . C27 C 1.1021(3) 0.3048(3) 1.1791(3) 0.0280(11) Uani 1 1 d . . . H27 H 1.1137 0.2906 1.2399 0.034 Uiso 1 1 calc R . . C28 C 1.1744(3) 0.2604(3) 1.1242(3) 0.0334(11) Uani 1 1 d . . . H28 H 1.2363 0.2154 1.1472 0.04 Uiso 1 1 calc R . . C1A C 0.1137(3) 0.8903(3) 0.3382(2) 0.0167(9) Uani 1 1 d . . . C2A C 0.2054(3) 0.8698(3) 0.3615(2) 0.0173(9) Uani 1 1 d . . . H2A H 0.2377 0.9135 0.3265 0.021 Uiso 1 1 calc R . . C3A C 0.2494(3) 0.7865(3) 0.4349(2) 0.0173(9) Uani 1 1 d . . . C4A C 0.2029(3) 0.7218(3) 0.4860(2) 0.0170(9) Uani 1 1 d . . . H4A H 0.2336 0.6648 0.5364 0.02 Uiso 1 1 calc R . . C5A C 0.1124(3) 0.7389(3) 0.4648(2) 0.0159(9) Uani 1 1 d . . . C6A C 0.0678(3) 0.8244(3) 0.3917(2) 0.0154(9) Uani 1 1 d . . . C7A C 0.0657(3) 0.6641(3) 0.5207(2) 0.0207(10) Uani 1 1 d . . . H7A1 H 0.0851 0.6345 0.5843 0.025 Uiso 1 1 calc R . . H7A2 H -0.0056 0.6995 0.5212 0.025 Uiso 1 1 calc R . . O1A O -0.02331(19) 0.8474(2) 0.36951(17) 0.0225(7) Uani 1 1 d . . . H1A H -0.044 0.8036 0.4057 0.034 Uiso 1 1 calc R . . O2A O 0.40196(19) 0.82857(19) 0.38402(17) 0.0242(7) Uani 1 1 d . . . O3A O 0.4240(2) 0.65668(19) 0.46494(19) 0.0277(7) Uani 1 1 d . . . O4A O 0.3591(2) 0.7710(2) 0.54590(18) 0.0312(8) Uani 1 1 d . . . S1A S 0.36763(7) 0.75810(7) 0.46062(6) 0.0180(3) Uani 1 1 d . . . C1B C 0.1690(3) 0.4898(3) 0.5210(3) 0.0195(9) Uani 1 1 d . . . H1B H 0.205 0.4796 0.5676 0.023 Uiso 1 1 calc R . . C2B C 0.1922(3) 0.4140(3) 0.4894(3) 0.0187(9) Uani 1 1 d . . . C3B C 0.1422(3) 0.4291(3) 0.4194(2) 0.0181(9) Uani 1 1 d . . . H3B H 0.1594 0.3769 0.3975 0.022 Uiso 1 1 calc R . . C4B C 0.0669(3) 0.5196(3) 0.3805(2) 0.0157(9) Uani 1 1 d . . . C5B C 0.0425(3) 0.5939(3) 0.4160(3) 0.0178(9) Uani 1 1 d . . . C6B C 0.0930(3) 0.5817(3) 0.4852(2) 0.0200(10) Uani 1 1 d . . . C7B C 0.0154(3) 0.5341(3) 0.3029(2) 0.0191(9) Uani 1 1 d . . . H7B1 H -0.0543 0.5746 0.3092 0.023 Uiso 1 1 calc R . . H7B2 H 0.0213 0.4686 0.3063 0.023 Uiso 1 1 calc R . . O1B O -0.03484(19) 0.68245(19) 0.38376(17) 0.0224(7) Uani 1 1 d . . . H1B1 H -0.0594 0.6818 0.3425 0.034 Uiso 1 1 calc R . . O2B O 0.2683(2) 0.2734(2) 0.63746(18) 0.0291(7) Uani 1 1 d . . . O3B O 0.3770(2) 0.3072(2) 0.50667(18) 0.0292(7) Uani 1 1 d . . . O4B O 0.2732(3) 0.2263(2) 0.5118(2) 0.0512(10) Uani 1 1 d . . . S1B S 0.28503(8) 0.29654(8) 0.53902(7) 0.0237(3) Uani 1 1 d . . . C1C C 0.0570(3) 0.5851(3) 0.2108(2) 0.0171(9) Uani 1 1 d . . . C2C C 0.1371(3) 0.5281(3) 0.1702(2) 0.0176(9) Uani 1 1 d . . . H2C H 0.1634 0.4578 0.1989 0.021 Uiso 1 1 calc R . . C3C C 0.1788(3) 0.5738(3) 0.0878(3) 0.0191(9) Uani 1 1 d . . . C4C C 0.1406(3) 0.6765(3) 0.0455(3) 0.0192(9) Uani 1 1 d . . . H4C H 0.1694 0.7069 -0.011 0.023 Uiso 1 1 calc R . . C5C C 0.0613(3) 0.7353(3) 0.0844(2) 0.0168(9) Uani 1 1 d . . . C6C C 0.0203(3) 0.6877(3) 0.1668(3) 0.0194(9) Uani 1 1 d . . . C7C C 0.0226(3) 0.8478(3) 0.0364(3) 0.0199(9) Uani 1 1 d . . . H7C1 H 0.0301 0.8641 -0.0304 0.024 Uiso 1 1 calc R . . H7C2 H -0.0474 0.8762 0.053 0.024 Uiso 1 1 calc R . . O1C O -0.06215(19) 0.7424(2) 0.20645(17) 0.0236(7) Uani 1 1 d . . . H1C H -0.0783 0.8031 0.1745 0.035 Uiso 1 1 calc R . . O2C O 0.2973(2) 0.4014(2) 0.0794(2) 0.0318(8) Uani 1 1 d . . . O3C O 0.36190(19) 0.52564(19) 0.04891(17) 0.0212(6) Uani 1 1 d . . . O4C O 0.2631(2) 0.5441(2) -0.06072(18) 0.0327(8) Uani 1 1 d . . . S1C S 0.28322(8) 0.50598(7) 0.03395(7) 0.0206(3) Uani 1 1 d . . . C1D C 0.0751(3) 0.8946(3) 0.0616(2) 0.0180(9) Uani 1 1 d . . . C2D C 0.1539(3) 0.9136(3) 0.0076(3) 0.0178(9) Uani 1 1 d . . . H2D H 0.174 0.8986 -0.0465 0.021 Uiso 1 1 calc R . . C3D C 0.2033(3) 0.9543(3) 0.0324(3) 0.0182(9) Uani 1 1 d . . . C4D C 0.1762(3) 0.9755(3) 0.1120(3) 0.0200(9) Uani 1 1 d . . . H4D H 0.2115 1.0018 0.1289 0.024 Uiso 1 1 calc R . . C5D C 0.0964(3) 0.9579(3) 0.1676(2) 0.0161(9) Uani 1 1 d . . . C6D C 0.0475(3) 0.9186(3) 0.1409(2) 0.0176(9) Uani 1 1 d . . . C7D C 0.0677(3) 0.9807(3) 0.2549(2) 0.0184(9) Uani 1 1 d . . . H7D1 H -0.0036 1.0046 0.2649 0.022 Uiso 1 1 calc R . . H7D2 H 0.0876 1.0346 0.2478 0.022 Uiso 1 1 calc R . . O1D O -0.03420(19) 0.9047(2) 0.18979(17) 0.0233(7) Uani 1 1 d . . . H1D H -0.0461 0.9231 0.2343 0.035 Uiso 1 1 calc R . . O2D O 0.3461(2) 0.9132(2) -0.0833(2) 0.0436(9) Uani 1 1 d . . . O3D O 0.3581(3) 0.9876(4) 0.0147(2) 0.0708(14) Uani 1 1 d . . . O4D O 0.2521(2) 1.0847(2) -0.1076(2) 0.0422(9) Uani 1 1 d . . . S1D S 0.29762(8) 0.98591(8) -0.04074(7) 0.0246(3) 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 O1W 0.0295(18) 0.0226(17) 0.0235(16) -0.0078(13) 0.0032(14) -0.0113(15) O2W 0.035(2) 0.0216(18) 0.0323(18) -0.0107(15) -0.0012(15) -0.0051(15) O3W 0.0368(19) 0.0175(17) 0.0350(18) -0.0085(14) 0.0050(16) -0.0112(15) O4W 0.026(2) 0.045(2) 0.045(2) -0.0092(17) -0.0109(16) -0.0132(17) O5W 0.049(2) 0.047(2) 0.040(2) -0.0184(18) -0.0051(17) -0.0226(19) O6W 0.046(2) 0.048(2) 0.0311(18) -0.0168(16) -0.0032(17) -0.0069(19) Cl1 0.0206(6) 0.0319(6) 0.0308(6) -0.0162(5) -0.0022(5) -0.0101(5) C1 0.014(2) 0.024(2) 0.027(2) -0.018(2) -0.0025(18) -0.0022(19) C2 0.020(2) 0.025(3) 0.025(2) -0.008(2) -0.0007(19) -0.005(2) C3 0.015(2) 0.024(2) 0.025(2) -0.0086(19) 0.0022(19) -0.0066(19) C4 0.016(2) 0.017(2) 0.025(2) -0.0109(19) -0.0041(18) -0.0019(19) C5 0.019(2) 0.024(2) 0.020(2) -0.0061(19) -0.0048(18) -0.005(2) C6 0.022(2) 0.019(2) 0.031(2) -0.0128(19) 0.001(2) -0.007(2) N7 0.018(2) 0.026(2) 0.0199(18) -0.0090(15) -0.0016(15) -0.0069(17) C8 0.014(2) 0.021(2) 0.017(2) -0.0078(18) -0.0013(18) -0.005(2) N8 0.020(2) 0.0166(19) 0.034(2) -0.0126(16) -0.0089(16) -0.0018(16) N9 0.0147(19) 0.0197(19) 0.0207(17) -0.0119(15) 0.0008(15) -0.0046(16) C10 0.010(2) 0.020(2) 0.021(2) -0.0072(18) -0.0040(18) -0.0062(19) N10 0.0170(19) 0.0199(19) 0.0220(19) -0.0095(15) -0.0022(15) -0.0035(16) N11 0.0147(18) 0.0167(18) 0.0199(17) -0.0080(15) 0.0034(15) -0.0058(15) C12 0.019(2) 0.021(2) 0.023(2) -0.0105(18) -0.0034(18) -0.0037(19) C13 0.023(2) 0.022(2) 0.020(2) -0.0085(18) -0.0010(18) -0.010(2) C14 0.020(2) 0.020(2) 0.032(2) -0.0161(19) 0.0013(19) -0.0048(19) C15 0.024(2) 0.017(2) 0.024(2) -0.0060(18) -0.0108(19) -0.0038(19) C16 0.025(3) 0.022(2) 0.025(2) -0.0076(19) -0.0040(19) -0.012(2) C17 0.020(2) 0.024(2) 0.024(2) -0.0098(19) 0.0025(19) -0.013(2) N18 0.025(2) 0.026(2) 0.0265(19) -0.0102(16) -0.0025(17) -0.0136(17) C19 0.025(3) 0.022(2) 0.022(2) -0.0092(19) 0.002(2) -0.013(2) N19 0.025(2) 0.054(3) 0.030(2) -0.0277(19) 0.0072(17) -0.021(2) N20 0.027(2) 0.033(2) 0.030(2) -0.0184(17) 0.0065(17) -0.0175(18) C21 0.018(2) 0.032(3) 0.030(2) -0.017(2) 0.0019(19) -0.014(2) N21 0.032(2) 0.026(2) 0.030(2) -0.0173(17) 0.0044(17) -0.0121(18) N22 0.050(3) 0.047(3) 0.050(3) -0.033(2) 0.026(2) -0.040(2) C23 0.032(3) 0.042(3) 0.037(3) -0.025(2) 0.017(2) -0.028(3) C24 0.048(3) 0.056(3) 0.024(2) -0.024(2) 0.009(2) -0.034(3) C25 0.035(3) 0.043(3) 0.026(2) -0.012(2) -0.005(2) -0.020(2) C26 0.028(3) 0.033(3) 0.024(2) -0.011(2) 0.004(2) -0.023(2) Cl26 0.0273(6) 0.0414(7) 0.0297(6) -0.0185(5) 0.0017(5) -0.0158(5) C27 0.029(3) 0.038(3) 0.023(2) -0.009(2) -0.002(2) -0.020(2) C28 0.028(3) 0.038(3) 0.038(3) -0.016(2) 0.003(2) -0.017(2) C1A 0.018(2) 0.016(2) 0.014(2) -0.0087(17) -0.0001(17) -0.0021(18) C2A 0.018(2) 0.020(2) 0.014(2) -0.0085(18) 0.0012(17) -0.0058(19) C3A 0.020(2) 0.019(2) 0.016(2) -0.0110(18) -0.0027(17) -0.0042(19) C4A 0.023(2) 0.018(2) 0.0112(19) -0.0065(17) -0.0007(17) -0.0077(19) C5A 0.017(2) 0.017(2) 0.017(2) -0.0097(18) 0.0007(17) -0.0069(18) C6A 0.011(2) 0.023(2) 0.016(2) -0.0135(18) 0.0025(17) -0.0041(18) C7A 0.022(2) 0.028(2) 0.014(2) -0.0106(18) -0.0013(18) -0.007(2) O1A 0.0155(16) 0.0262(16) 0.0254(15) -0.0105(13) 0.0002(12) -0.0071(13) O2A 0.0198(16) 0.0208(16) 0.0253(15) 0.0009(12) -0.0048(13) -0.0089(13) O3A 0.0198(17) 0.0167(16) 0.0415(17) -0.0085(13) -0.0062(14) -0.0023(13) O4A 0.0229(17) 0.054(2) 0.0249(16) -0.0226(15) -0.0034(13) -0.0127(16) S1A 0.0169(6) 0.0179(6) 0.0184(5) -0.0066(4) -0.0032(4) -0.0048(5) C1B 0.017(2) 0.023(2) 0.018(2) -0.0013(18) -0.0070(18) -0.011(2) C2B 0.017(2) 0.018(2) 0.022(2) -0.0056(18) -0.0050(18) -0.0071(19) C3B 0.020(2) 0.022(2) 0.018(2) -0.0093(18) 0.0062(18) -0.015(2) C4B 0.015(2) 0.019(2) 0.0112(19) -0.0005(17) -0.0014(17) -0.0096(19) C5B 0.015(2) 0.017(2) 0.019(2) -0.0045(18) -0.0007(18) -0.0066(19) C6B 0.022(2) 0.027(2) 0.015(2) -0.0078(18) 0.0021(18) -0.014(2) C7B 0.021(2) 0.020(2) 0.018(2) -0.0065(17) -0.0039(18) -0.0077(19) O1B 0.0189(16) 0.0236(17) 0.0234(15) -0.0058(13) -0.0071(12) -0.0068(14) O2B 0.0257(17) 0.0341(18) 0.0208(15) 0.0018(13) -0.0059(13) -0.0145(14) O3B 0.0197(17) 0.0326(18) 0.0223(15) -0.0039(13) -0.0007(13) -0.0044(14) O4B 0.069(3) 0.0240(19) 0.066(2) -0.0120(17) -0.047(2) -0.0060(18) S1B 0.0265(7) 0.0208(6) 0.0222(6) -0.0034(5) -0.0101(5) -0.0075(5) C1C 0.015(2) 0.021(2) 0.018(2) -0.0064(18) -0.0047(17) -0.0084(19) C2C 0.018(2) 0.016(2) 0.016(2) 0.0005(17) -0.0074(18) -0.0071(19) C3C 0.019(2) 0.018(2) 0.025(2) -0.0097(19) -0.0059(18) -0.0060(19) C4C 0.021(2) 0.023(2) 0.017(2) -0.0053(18) -0.0040(18) -0.011(2) C5C 0.020(2) 0.018(2) 0.013(2) -0.0046(17) -0.0051(17) -0.0061(19) C6C 0.017(2) 0.027(3) 0.019(2) -0.0136(19) -0.0075(18) -0.005(2) C7C 0.021(2) 0.018(2) 0.019(2) -0.0089(18) -0.0056(18) -0.0023(19) O1C 0.0173(16) 0.0215(16) 0.0231(15) -0.0071(13) -0.0043(12) 0.0010(13) O2C 0.0325(19) 0.0238(17) 0.0412(18) -0.0165(14) 0.0042(15) -0.0112(14) O3C 0.0190(16) 0.0218(16) 0.0217(15) -0.0062(12) -0.0028(12) -0.0075(13) O4C 0.0305(18) 0.0429(19) 0.0216(15) -0.0188(14) -0.0074(14) -0.0017(15) S1C 0.0215(6) 0.0197(6) 0.0214(5) -0.0103(4) -0.0019(5) -0.0055(5) C1D 0.017(2) 0.015(2) 0.017(2) 0.0002(17) -0.0089(18) -0.0030(18) C2D 0.019(2) 0.012(2) 0.017(2) -0.0037(17) -0.0057(18) -0.0003(18) C3D 0.017(2) 0.015(2) 0.018(2) -0.0062(17) -0.0032(18) -0.0008(18) C4D 0.017(2) 0.016(2) 0.025(2) -0.0069(18) -0.0057(18) -0.0035(18) C5D 0.016(2) 0.010(2) 0.018(2) -0.0041(17) -0.0080(17) 0.0011(18) C6D 0.015(2) 0.013(2) 0.016(2) -0.0018(17) -0.0049(18) 0.0021(18) C7D 0.017(2) 0.018(2) 0.020(2) -0.0098(18) -0.0013(18) -0.0039(18) O1D 0.0173(16) 0.0278(17) 0.0227(15) -0.0107(13) 0.0038(13) -0.0075(13) O2D 0.049(2) 0.0341(19) 0.046(2) -0.0241(16) 0.0290(17) -0.0203(17) O3D 0.052(3) 0.168(4) 0.0311(19) -0.045(2) 0.0170(18) -0.076(3) O4D 0.034(2) 0.0199(18) 0.059(2) -0.0010(16) 0.0036(17) -0.0130(15) S1D 0.0229(6) 0.0323(7) 0.0245(6) -0.0149(5) 0.0019(5) -0.0129(5) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 O1W H1W1 0.844(19) . ? O1W H2W1 0.831(19) . ? O2W H1W2 0.848(19) . ? O2W H2W2 0.853(19) . ? O3W H1W3 0.850(19) . ? O3W H2W3 0.851(19) . ? O4W H1W4 0.818(19) . ? O4W H2W4 0.844(19) . ? O5W H1W5 0.892(19) . ? O5W H2W5 0.847(19) . ? O6W H1W6 0.870(19) . ? O6W H2W6 0.860(19) . ? Cl1 C1 1.743(4) . ? C1 C2 1.377(6) . ? C1 C6 1.382(6) . ? C2 C3 1.384(6) . ? C2 H2 0.95 . ? C3 C4 1.382(6) . ? C3 H3 0.95 . ? C4 C5 1.384(6) . ? C4 N7 1.438(5) . ? C5 C6 1.390(6) . ? C5 H5 0.95 . ? C6 H6 0.95 . ? N7 C8 1.331(5) . ? N7 H7A 0.92 . ? N7 H7B 0.92 . ? C8 N8 1.307(5) . ? C8 N9 1.370(5) . ? N8 H8A 0.88 . ? N8 H8B 0.88 . ? N9 C10 1.396(5) . ? N9 H9A 0.92 . ? N9 H9B 0.92 . ? C10 N11 1.300(5) . ? C10 N10 1.323(5) . ? N10 H10A 0.88 . ? N10 H10B 0.88 . ? N11 C12 1.471(5) . ? N11 H11A 0.92 . ? C12 C13 1.517(5) . ? C12 H12A 0.99 . ? C12 H12B 0.99 . ? C13 C14 1.532(6) . ? C13 H13A 0.99 . ? C13 H13B 0.99 . ? C14 C15 1.535(5) . ? C14 H14A 0.99 . ? C14 H14B 0.99 . ? C15 C16 1.523(6) . ? C15 H15A 0.99 . ? C15 H15B 0.99 . ? C16 C17 1.513(5) . ? C16 H16A 0.99 . ? C16 H16B 0.99 . ? C17 N18 1.464(5) . ? C17 H17A 0.99 . ? C17 H17B 0.99 . ? N18 C19 1.306(5) . ? N18 H18A 0.92 . ? N18 H18B 0.92 . ? C19 N19 1.306(5) . ? C19 N20 1.393(5) . ? N19 H19A 0.88 . ? N19 H19B 0.88 . ? N20 C21 1.372(5) . ? N20 H20B 0.92 . ? C21 N21 1.288(5) . ? C21 N22 1.332(5) . ? N21 H21A 0.88 . ? N22 C23 1.434(5) . ? N22 H22B 0.92 . ? C23 C28 1.370(6) . ? C23 C24 1.386(7) . ? C24 C25 1.383(6) . ? C24 H24 0.95 . ? C25 C26 1.372(6) . ? C25 H25 0.95 . ? C26 C27 1.375(6) . ? C26 Cl26 1.749(4) . ? C27 C28 1.386(6) . ? C27 H27 0.95 . ? C28 H28 0.95 . ? C1A C2A 1.399(6) . ? C1A C6A 1.404(5) . ? C1A C7D 1.527(5) . ? C2A C3A 1.382(5) . ? C2A H2A 0.95 . ? C3A C4A 1.390(5) . ? C3A S1A 1.769(4) . ? C4A C5A 1.386(6) . ? C4A H4A 0.95 . ? C5A C6A 1.396(5) . ? C5A C7A 1.523(5) . ? C6A O1A 1.373(5) . ? C7A C6B 1.509(5) . ? C7A H7A1 0.99 . ? C7A H7A2 0.99 . ? O1A H1A 0.84 . ? O2A S1A 1.466(3) . ? O3A S1A 1.450(3) . ? O4A S1A 1.443(3) . ? C1B C2B 1.383(5) . ? C1B C6B 1.404(6) . ? C1B H1B 0.95 . ? C2B C3B 1.386(5) . ? C2B S1B 1.775(4) . ? C3B C4B 1.396(5) . ? C3B H3B 0.95 . ? C4B C5B 1.399(5) . ? C4B C7B 1.511(5) . ? C5B O1B 1.377(5) . ? C5B C6B 1.400(5) . ? C7B C1C 1.521(5) . ? C7B H7B1 0.99 . ? C7B H7B2 0.99 . ? O1B H1B1 0.84 . ? O2B S1B 1.464(3) . ? O3B S1B 1.448(3) . ? O4B S1B 1.450(3) . ? C1C C6C 1.389(6) . ? C1C C2C 1.392(5) . ? C2C C3C 1.392(5) . ? C2C H2C 0.95 . ? C3C C4C 1.388(5) . ? C3C S1C 1.775(4) . ? C4C C5C 1.384(5) . ? C4C H4C 0.95 . ? C5C C6C 1.396(5) . ? C5C C7C 1.524(5) . ? C6C O1C 1.385(5) . ? C7C C1D 1.513(6) . ? C7C H7C1 0.99 . ? C7C H7C2 0.99 . ? O1C H1C 0.84 . ? O2C S1C 1.459(3) . ? O3C S1C 1.459(3) . ? O4C S1C 1.442(3) . ? C1D C2D 1.393(5) . ? C1D C6D 1.409(5) . ? C2D C3D 1.390(6) . ? C2D H2D 0.95 . ? C3D C4D 1.392(5) . ? C3D S1D 1.766(4) . ? C4D C5D 1.407(5) . ? C4D H4D 0.95 . ? C5D C6D 1.383(6) . ? C5D C7D 1.523(5) . ? C6D O1D 1.378(4) . ? C7D H7D1 0.99 . ? C7D H7D2 0.99 . ? O1D H1D 0.84 . ? O2D S1D 1.436(3) . ? O3D S1D 1.438(4) . ? O4D S1D 1.457(3) . ? 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 H1W1 O1W H2W1 113(4) . . ? H1W2 O2W H2W2 113(4) . . ? H1W3 O3W H2W3 106(4) . . ? H1W4 O4W H2W4 121(4) . . ? H1W5 O5W H2W5 108(4) . . ? H1W6 O6W H2W6 105(4) . . ? C2 C1 C6 121.6(4) . . ? C2 C1 Cl1 119.5(3) . . ? C6 C1 Cl1 118.9(3) . . ? C1 C2 C3 119.1(4) . . ? C1 C2 H2 120.5 . . ? C3 C2 H2 120.5 . . ? C4 C3 C2 120.3(4) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C3 C4 C5 120.2(4) . . ? C3 C4 N7 119.3(4) . . ? C5 C4 N7 120.5(4) . . ? C4 C5 C6 119.9(4) . . ? C4 C5 H5 120 . . ? C6 C5 H5 120 . . ? C1 C6 C5 118.9(4) . . ? C1 C6 H6 120.5 . . ? C5 C6 H6 120.5 . . ? C8 N7 C4 123.6(3) . . ? C8 N7 H7A 106.4 . . ? C4 N7 H7A 106.4 . . ? C8 N7 H7B 106.4 . . ? C4 N7 H7B 106.4 . . ? H7A N7 H7B 106.5 . . ? N8 C8 N7 120.8(4) . . ? N8 C8 N9 120.4(4) . . ? N7 C8 N9 118.8(4) . . ? C8 N8 H8A 120 . . ? C8 N8 H8B 120 . . ? H8A N8 H8B 120 . . ? C8 N9 C10 123.8(3) . . ? C8 N9 H9A 106.4 . . ? C10 N9 H9A 106.4 . . ? C8 N9 H9B 106.4 . . ? C10 N9 H9B 106.4 . . ? H9A N9 H9B 106.4 . . ? N11 C10 N10 125.1(4) . . ? N11 C10 N9 116.6(3) . . ? N10 C10 N9 118.2(3) . . ? C10 N10 H10A 120 . . ? C10 N10 H10B 120 . . ? H10A N10 H10B 120 . . ? C10 N11 C12 123.4(3) . . ? C10 N11 H11A 106.5 . . ? C12 N11 H11A 106.5 . . ? N11 C12 C13 110.4(3) . . ? N11 C12 H12A 109.6 . . ? C13 C12 H12A 109.6 . . ? N11 C12 H12B 109.6 . . ? C13 C12 H12B 109.6 . . ? H12A C12 H12B 108.1 . . ? C12 C13 C14 111.2(3) . . ? C12 C13 H13A 109.4 . . ? C14 C13 H13A 109.4 . . ? C12 C13 H13B 109.4 . . ? C14 C13 H13B 109.4 . . ? H13A C13 H13B 108 . . ? C13 C14 C15 114.7(3) . . ? C13 C14 H14A 108.6 . . ? C15 C14 H14A 108.6 . . ? C13 C14 H14B 108.6 . . ? C15 C14 H14B 108.6 . . ? H14A C14 H14B 107.6 . . ? C16 C15 C14 115.4(3) . . ? C16 C15 H15A 108.4 . . ? C14 C15 H15A 108.4 . . ? C16 C15 H15B 108.4 . . ? C14 C15 H15B 108.4 . . ? H15A C15 H15B 107.5 . . ? C17 C16 C15 113.5(3) . . ? C17 C16 H16A 108.9 . . ? C15 C16 H16A 108.9 . . ? C17 C16 H16B 108.9 . . ? C15 C16 H16B 108.9 . . ? H16A C16 H16B 107.7 . . ? N18 C17 C16 110.1(3) . . ? N18 C17 H17A 109.6 . . ? C16 C17 H17A 109.6 . . ? N18 C17 H17B 109.6 . . ? C16 C17 H17B 109.6 . . ? H17A C17 H17B 108.2 . . ? C19 N18 C17 124.1(3) . . ? C19 N18 H18A 106.3 . . ? C17 N18 H18A 106.3 . . ? C19 N18 H18B 106.3 . . ? C17 N18 H18B 106.3 . . ? H18A N18 H18B 106.4 . . ? N18 C19 N19 124.4(4) . . ? N18 C19 N20 119.9(3) . . ? N19 C19 N20 115.7(4) . . ? C19 N19 H19A 120 . . ? C19 N19 H19B 120 . . ? H19A N19 H19B 120 . . ? C21 N20 C19 124.9(3) . . ? C21 N20 H20B 106.1 . . ? C19 N20 H20B 106.1 . . ? N21 C21 N22 124.3(4) . . ? N21 C21 N20 120.1(4) . . ? N22 C21 N20 115.6(4) . . ? C21 N21 H21A 120 . . ? C21 N22 C23 123.2(4) . . ? C21 N22 H22B 106.5 . . ? C23 N22 H22B 106.5 . . ? C28 C23 C24 120.1(4) . . ? C28 C23 N22 120.1(5) . . ? C24 C23 N22 119.8(4) . . ? C25 C24 C23 120.4(4) . . ? C25 C24 H24 119.8 . . ? C23 C24 H24 119.8 . . ? C26 C25 C24 118.3(5) . . ? C26 C25 H25 120.9 . . ? C24 C25 H25 120.9 . . ? C25 C26 C27 122.4(4) . . ? C25 C26 Cl26 117.5(4) . . ? C27 C26 Cl26 120.1(3) . . ? C26 C27 C28 118.6(4) . . ? C26 C27 H27 120.7 . . ? C28 C27 H27 120.7 . . ? C23 C28 C27 120.3(5) . . ? C23 C28 H28 119.9 . . ? C27 C28 H28 119.9 . . ? C2A C1A C6A 118.1(3) . . ? C2A C1A C7D 120.0(3) . . ? C6A C1A C7D 121.9(4) . . ? C3A C2A C1A 120.7(4) . . ? C3A C2A H2A 119.7 . . ? C1A C2A H2A 119.7 . . ? C2A C3A C4A 120.0(4) . . ? C2A C3A S1A 120.3(3) . . ? C4A C3A S1A 119.6(3) . . ? C5A C4A C3A 121.2(4) . . ? C5A C4A H4A 119.4 . . ? C3A C4A H4A 119.4 . . ? C4A C5A C6A 118.2(3) . . ? C4A C5A C7A 119.4(3) . . ? C6A C5A C7A 122.4(4) . . ? O1A C6A C5A 121.0(3) . . ? O1A C6A C1A 117.3(3) . . ? C5A C6A C1A 121.7(4) . . ? C6B C7A C5A 113.5(3) . . ? C6B C7A H7A1 108.9 . . ? C5A C7A H7A1 108.9 . . ? C6B C7A H7A2 108.9 . . ? C5A C7A H7A2 108.9 . . ? H7A1 C7A H7A2 107.7 . . ? C6A O1A H1A 109.5 . . ? O4A S1A O3A 113.46(18) . . ? O4A S1A O2A 112.93(18) . . ? O3A S1A O2A 111.44(16) . . ? O4A S1A C3A 107.01(17) . . ? O3A S1A C3A 106.06(17) . . ? O2A S1A C3A 105.24(17) . . ? C2B C1B C6B 121.0(4) . . ? C2B C1B H1B 119.5 . . ? C6B C1B H1B 119.5 . . ? C1B C2B C3B 120.0(4) . . ? C1B C2B S1B 120.3(3) . . ? C3B C2B S1B 119.7(3) . . ? C2B C3B C4B 121.3(4) . . ? C2B C3B H3B 119.4 . . ? C4B C3B H3B 119.4 . . ? C3B C4B C5B 117.6(4) . . ? C3B C4B C7B 119.8(3) . . ? C5B C4B C7B 122.7(3) . . ? O1B C5B C4B 120.0(3) . . ? O1B C5B C6B 117.5(3) . . ? C4B C5B C6B 122.5(4) . . ? C5B C6B C1B 117.6(4) . . ? C5B C6B C7A 121.1(4) . . ? C1B C6B C7A 121.3(4) . . ? C4B C7B C1C 111.8(3) . . ? C4B C7B H7B1 109.3 . . ? C1C C7B H7B1 109.3 . . ? C4B C7B H7B2 109.3 . . ? C1C C7B H7B2 109.3 . . ? H7B1 C7B H7B2 107.9 . . ? C5B O1B H1B1 109.5 . . ? O3B S1B O4B 113.0(2) . . ? O3B S1B O2B 111.63(17) . . ? O4B S1B O2B 111.76(19) . . ? O3B S1B C2B 107.54(17) . . ? O4B S1B C2B 107.02(19) . . ? O2B S1B C2B 105.37(18) . . ? C6C C1C C2C 118.4(3) . . ? C6C C1C C7B 122.4(3) . . ? C2C C1C C7B 119.2(3) . . ? C1C C2C C3C 120.1(4) . . ? C1C C2C H2C 119.9 . . ? C3C C2C H2C 119.9 . . ? C4C C3C C2C 120.2(4) . . ? C4C C3C S1C 117.2(3) . . ? C2C C3C S1C 122.5(3) . . ? C5C C4C C3C 121.0(4) . . ? C5C C4C H4C 119.5 . . ? C3C C4C H4C 119.5 . . ? C4C C5C C6C 117.7(4) . . ? C4C C5C C7C 119.3(3) . . ? C6C C5C C7C 123.0(3) . . ? O1C C6C C1C 117.1(3) . . ? O1C C6C C5C 120.2(4) . . ? C1C C6C C5C 122.6(4) . . ? C1D C7C C5C 111.8(3) . . ? C1D C7C H7C1 109.3 . . ? C5C C7C H7C1 109.3 . . ? C1D C7C H7C2 109.3 . . ? C5C C7C H7C2 109.3 . . ? H7C1 C7C H7C2 107.9 . . ? C6C O1C H1C 109.5 . . ? O4C S1C O2C 112.77(18) . . ? O4C S1C O3C 113.43(17) . . ? O2C S1C O3C 111.85(17) . . ? O4C S1C C3C 106.29(18) . . ? O2C S1C C3C 106.91(17) . . ? O3C S1C C3C 104.89(17) . . ? C2D C1D C6D 117.9(4) . . ? C2D C1D C7C 120.7(3) . . ? C6D C1D C7C 121.4(3) . . ? C3D C2D C1D 120.3(4) . . ? C3D C2D H2D 119.8 . . ? C1D C2D H2D 119.8 . . ? C2D C3D C4D 120.9(4) . . ? C2D C3D S1D 119.8(3) . . ? C4D C3D S1D 119.3(3) . . ? C3D C4D C5D 120.1(4) . . ? C3D C4D H4D 120 . . ? C5D C4D H4D 120 . . ? C6D C5D C4D 118.0(3) . . ? C6D C5D C7D 122.3(3) . . ? C4D C5D C7D 119.7(4) . . ? O1D C6D C5D 120.7(3) . . ? O1D C6D C1D 116.5(4) . . ? C5D C6D C1D 122.7(4) . . ? C5D C7D C1A 112.7(3) . . ? C5D C7D H7D1 109.1 . . ? C1A C7D H7D1 109.1 . . ? C5D C7D H7D2 109.1 . . ? C1A C7D H7D2 109.1 . . ? H7D1 C7D H7D2 107.8 . . ? C6D O1D H1D 109.5 . . ? O2D S1D O3D 114.1(2) . . ? O2D S1D O4D 111.3(2) . . ? O3D S1D O4D 110.5(2) . . ? O2D S1D C3D 107.00(18) . . ? O3D S1D C3D 106.76(19) . . ? O4D S1D C3D 106.74(18) . . ? 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 C6 N7 C8 N9 38.9(4) . . . . ? N7 C8 N9 C10 -151.5(3) . . . . ? C8 N9 C10 N11 -145.7(4) . . . . ? N9 C10 N11 C12 -175.6(3) . . . . ? C10 N11 C12 C13 133.6(4) . . . . ? N11 C12 C13 C14 -179.1(3) . . . . ? C12 C13 C14 C15 58.3(5) . . . . ? C13 C14 C15 C16 52.4(5) . . . . ? C14 C15 C16 C17 56.5(5) . . . . ? C15 C16 C17 N18 172.1(3) . . . . ? C16 C17 N18 C19 155.1(4) . . . . ? C17 N18 C19 N20 -174.2(4) . . . . ? N18 C19 N20 C21 34.2(6) . . . . ? C19 N20 C21 N22 -146.3(4) . . . . ? N20 C21 N22 C23 -163.5(4) . . . . ? # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material 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 _platon_squeeze_void_content 1 0.344 0.563 0.731 38 13 ' ' 2 0.500 0.000 0.500 230 44 ' ' 3 0.656 0.437 0.269 38 13 ' ' _platon_squeeze_details ; 'About three disordered methanol molecules were squeezed' ; _chemical_name_common "'para-sulfonatocalix(4)arene Chlorhexidine'" # Attachment 'C4diA-chlorhex.cif' data_calix[4]dimethoxycarboxylicacidChlorhexidine _database_code_depnum_ccdc_archive 'CCDC 661948' _audit_creation_method SHELXL-97 #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ' calix[4]arene dimethoxycarboxylic acid Chlorhexidine' ; _chemical_name_common "' calix(4)arene dimethoxycarboxylic acid Chlorhexidine'" _chemical_formula_moiety '1(C22 H30 Cl2 N10) 1(C32 H28 O8) 1(H2 O1)' _chemical_formula_sum 'C54 H60 Cl2 N10 O9' _chemical_formula_weight 1064.02 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.104(2) _cell_length_b 14.629(3) _cell_length_c 19.376(4) _cell_angle_alpha 69.71(3) _cell_angle_beta 87.37(3) _cell_angle_gamma 85.17(3) _cell_volume 2676.3(9) _cell_formula_units_Z 2 _cell_measurement_temperature 110(2) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description parallepiped _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.03 _exptl_crystal_density_diffrn 1.320 _exptl_crystal_F_000 1120 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.187 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kappa CCD' _diffrn_measurement_method rotation _diffrn_reflns_av_R_equivalents 0 _diffrn_reflns_av_unetI/netI 0.3241 _diffrn_reflns_number 7664 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 25.07 _diffrn_reflns_theta_full 25.07 _diffrn_measured_fraction_theta_full 0.806 _diffrn_measured_fraction_theta_max 0.806 _reflns_number_total 7664 _reflns_number_gt 2204 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect data collection software (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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.Restraints has been used to fix the solvent geometry. ; _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^)+(0.0648P)^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_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.0051(9) _refine_ls_number_reflns 7664 _refine_ls_number_parameters 683 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.2945 _refine_ls_R_factor_gt 0.088 _refine_ls_wR_factor_ref 0.2504 _refine_ls_wR_factor_gt 0.1712 _refine_ls_goodness_of_fit_ref 0.896 _refine_ls_restrained_S_all 0.904 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.294 _refine_diff_density_min -0.292 _refine_diff_density_rms 0.061 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 O1A O 0.1324(6) 0.3732(4) 0.2188(3) 0.0490(19) Uani 1 1 d . . . C1A C 0.1814(9) 0.3803(8) 0.0950(5) 0.047(3) Uani 1 1 d . . . C2A C 0.1895(8) 0.4362(8) 0.0201(5) 0.048(3) Uani 1 1 d . . . H2A H 0.2191 0.4058 -0.0145 0.058 Uiso 1 1 calc R . . C3A C 0.1540(9) 0.5370(8) -0.0040(5) 0.047(3) Uani 1 1 d . . . H3A H 0.1632 0.575 -0.0546 0.056 Uiso 1 1 calc R . . C4A C 0.1060(8) 0.5809(7) 0.0455(5) 0.048(3) Uani 1 1 d . . . H4A H 0.0805 0.6489 0.0283 0.057 Uiso 1 1 calc R . . C5A C 0.0943(9) 0.5272(8) 0.1200(5) 0.046(3) Uani 1 1 d . . . C6A C 0.1351(9) 0.4289(7) 0.1425(5) 0.040(3) Uani 1 1 d . . . C7A C 0.2509(10) 0.3829(8) 0.2517(5) 0.074(4) Uani 1 1 d . . . H7A1 H 0.2592 0.4529 0.2434 0.089 Uiso 1 1 calc R . . H7A2 H 0.3281 0.3594 0.2276 0.089 Uiso 1 1 calc R . . C8A C 0.2536(12) 0.3270(14) 0.3326(6) 0.100(6) Uani 1 1 d . . . O9A O 0.3208(11) 0.3679(11) 0.3689(5) 0.191(7) Uani 1 1 d . . . O10A O 0.1947(12) 0.2562(6) 0.3622(4) 0.125(4) Uani 1 1 d . . . C1AB C 0.0365(9) 0.5721(7) 0.1749(5) 0.057(3) Uani 1 1 d . . . H1A1 H 0.0683 0.6383 0.1623 0.068 Uiso 1 1 calc R . . H1A2 H 0.0696 0.5322 0.2244 0.068 Uiso 1 1 calc R . . O1B O -0.1256(5) 0.4066(4) 0.2453(3) 0.0508(19) Uani 1 1 d . . . H1B H -0.0427 0.409 0.2433 0.061 Uiso 1 1 calc R . . C1B C -0.1152(10) 0.5800(8) 0.1776(5) 0.050(3) Uani 1 1 d . . . C2B C -0.1872(12) 0.6698(8) 0.1483(5) 0.061(3) Uani 1 1 d . . . H2B H -0.1404 0.7269 0.1267 0.073 Uiso 1 1 calc R . . C3B C -0.3219(11) 0.6786(8) 0.1494(5) 0.065(3) Uani 1 1 d . . . H3B H -0.3676 0.7411 0.1286 0.078 Uiso 1 1 calc R . . C4B C -0.3938(10) 0.5962(8) 0.1808(5) 0.063(3) Uani 1 1 d . . . H4B H -0.4881 0.6022 0.1819 0.075 Uiso 1 1 calc R . . C5B C -0.3257(9) 0.5059(7) 0.2104(5) 0.047(3) Uani 1 1 d . . . C6B C -0.1862(10) 0.5007(7) 0.2093(5) 0.042(3) Uani 1 1 d . . . C1BC C -0.3978(8) 0.4143(7) 0.2417(5) 0.049(3) Uani 1 1 d . . . H1B1 H -0.489 0.4305 0.2569 0.058 Uiso 1 1 calc R . . H1B2 H -0.3512 0.369 0.2857 0.058 Uiso 1 1 calc R . . O1C O -0.2712(6) 0.2242(4) 0.2602(3) 0.0455(18) Uani 1 1 d . . . C1C C -0.4039(9) 0.3646(7) 0.1841(5) 0.042(3) Uani 1 1 d . . . C2C C -0.4681(9) 0.4100(7) 0.1174(6) 0.054(3) Uani 1 1 d . . . H2C H -0.5171 0.4712 0.1087 0.065 Uiso 1 1 calc R . . C3C C -0.4619(9) 0.3676(8) 0.0634(5) 0.049(3) Uani 1 1 d . . . H3C H -0.5091 0.3988 0.0191 0.059 Uiso 1 1 calc R . . C4C C -0.3885(10) 0.2810(8) 0.0733(5) 0.053(3) Uani 1 1 d . . . H4C H -0.3818 0.2551 0.0345 0.064 Uiso 1 1 calc R . . C5C C -0.3229(9) 0.2296(8) 0.1394(5) 0.045(3) Uani 1 1 d . . . C6C C -0.3366(9) 0.2734(8) 0.1924(5) 0.046(3) Uani 1 1 d . . . C7C C -0.3433(10) 0.1508(7) 0.3137(5) 0.061(3) Uani 1 1 d . . . H7C1 H -0.4066 0.125 0.2888 0.073 Uiso 1 1 calc R . . H7C2 H -0.3944 0.1794 0.3471 0.073 Uiso 1 1 calc R . . C8C C -0.2471(11) 0.0697(7) 0.3571(6) 0.060(3) Uani 1 1 d . . . O9C O -0.1375(7) 0.0548(5) 0.3314(4) 0.075(2) Uani 1 1 d . . . O10C O -0.2922(7) 0.0177(5) 0.4195(3) 0.080(3) Uani 1 1 d . . . C1CD C -0.2379(9) 0.1375(7) 0.1474(5) 0.050(3) Uani 1 1 d . . . H1C1 H -0.2856 0.0968 0.1267 0.06 Uiso 1 1 calc R . . H1C2 H -0.2256 0.1005 0.2004 0.06 Uiso 1 1 calc R . . O1D O -0.0235(6) 0.2277(5) 0.1927(3) 0.0522(19) Uani 1 1 d . . . H1D H -0.1003 0.2167 0.2105 0.063 Uiso 1 1 calc R . . C1D C -0.1034(10) 0.1532(7) 0.1104(5) 0.048(3) Uani 1 1 d . . . C2D C -0.0715(10) 0.1219(7) 0.0510(5) 0.056(3) Uani 1 1 d . . . H2D H -0.1355 0.0893 0.0356 0.068 Uiso 1 1 calc R . . C3D C 0.0466(11) 0.1358(7) 0.0142(6) 0.063(3) Uani 1 1 d . . . H3D H 0.0647 0.1148 -0.0267 0.075 Uiso 1 1 calc R . . C4D C 0.1410(10) 0.1821(7) 0.0382(6) 0.056(3) Uani 1 1 d . . . H4D H 0.2245 0.1915 0.0131 0.068 Uiso 1 1 calc R . . C5D C 0.1181(9) 0.2150(7) 0.0970(5) 0.046(3) Uani 1 1 d . . . C6D C -0.0051(10) 0.1961(7) 0.1341(5) 0.053(3) Uani 1 1 d . . . C1DA C 0.2182(9) 0.2710(7) 0.1198(5) 0.049(3) Uani 1 1 d . . . H1D1 H 0.2252 0.2451 0.1741 0.059 Uiso 1 1 calc R . . H1D2 H 0.3065 0.2595 0.0988 0.059 Uiso 1 1 calc R . . Cl1P Cl 0.6511(3) 0.9486(2) 0.05866(15) 0.0800(11) Uani 1 1 d . . . C1P C 0.5637(11) 0.9527(7) 0.1386(6) 0.056(3) Uani 1 1 d . . . C2P C 0.4452(11) 1.0084(8) 0.1309(6) 0.066(3) Uani 1 1 d . . . H2P H 0.4079 1.0425 0.084 0.079 Uiso 1 1 calc R . . C3P C 0.3841(10) 1.0120(7) 0.1942(5) 0.057(3) Uani 1 1 d . . . H3P H 0.3022 1.0501 0.1911 0.068 Uiso 1 1 calc R . . C4P C 0.4373(11) 0.9620(7) 0.2630(6) 0.052(3) Uani 1 1 d . . . C5P C 0.5550(10) 0.9071(8) 0.2681(6) 0.069(4) Uani 1 1 d . . . H5P H 0.5929 0.8721 0.3147 0.082 Uiso 1 1 calc R . . C6P C 0.6171(11) 0.9035(7) 0.2047(6) 0.066(3) Uani 1 1 d . . . H6P H 0.6991 0.8657 0.2074 0.08 Uiso 1 1 calc R . . N1P N 0.3584(8) 0.9729(6) 0.3232(4) 0.062(3) Uani 1 1 d . . . H1P1 H 0.3548 1.0385 0.3165 0.075 Uiso 1 1 calc R . . H1P2 H 0.2739 0.9603 0.3152 0.075 Uiso 0 1 calc PR . . N2P N 0.4591(9) 0.8489(7) 0.4178(5) 0.065(3) Uani 1 1 d . . . H2P2 H 0.4173 0.8009 0.4087 0.078 Uiso 1 1 calc R . . N3P N 0.5139(9) 0.7095(7) 0.5167(5) 0.075(3) Uani 1 1 d . . . H3P2 H 0.6021 0.6877 0.5231 0.09 Uiso 1 1 calc R . . C7P C 0.3782(11) 0.9263(8) 0.3964(6) 0.055(3) Uani 1 1 d . . . N7P N 0.2984(8) 0.9579(6) 0.4410(5) 0.080(3) Uani 1 1 d . . . H7P1 H 0.2984 0.9255 0.4887 0.096 Uiso 1 1 calc R . . H7P2 H 0.2455 1.0112 0.4229 0.096 Uiso 1 1 calc R . . C8P C 0.5102(10) 0.8071(10) 0.4844(6) 0.059(3) Uani 1 1 d . . . N8P N 0.5630(9) 0.8580(7) 0.5210(5) 0.068(3) Uani 1 1 d . . . H8P1 H 0.5647 0.9219 0.5009 0.082 Uiso 1 1 calc R . . C9P C 0.4522(14) 0.6462(9) 0.4841(7) 0.101(5) Uani 1 1 d . . . H9P1 H 0.3617 0.6743 0.4676 0.122 Uiso 1 1 calc R . . H9P2 H 0.4445 0.5807 0.5218 0.122 Uiso 1 1 calc R . . C10P C 0.5352(16) 0.6367(10) 0.4188(8) 0.112(5) Uani 1 1 d . . . H10A H 0.5276 0.7004 0.3781 0.135 Uiso 1 1 calc R . . H10B H 0.4962 0.5884 0.4018 0.135 Uiso 1 1 calc R . . C11P C 0.6885(16) 0.6045(10) 0.4335(7) 0.110(5) Uani 1 1 d . . . H11A H 0.7299 0.6543 0.4476 0.132 Uiso 1 1 calc R . . H11B H 0.6974 0.5419 0.4752 0.132 Uiso 1 1 calc R . . C11R C 0.7614(16) 0.5925(11) 0.3676(7) 0.111(5) Uani 1 1 d . . . H11C H 0.7481 0.654 0.3252 0.133 Uiso 1 1 calc R . . H11D H 0.7228 0.5403 0.3551 0.133 Uiso 1 1 calc R . . C10R C 0.9079(17) 0.5672(9) 0.3792(6) 0.102(5) Uani 1 1 d . . . H10R H 0.9441 0.6135 0.3992 0.122 Uiso 1 1 calc R . . H10P H 0.9525 0.5752 0.3311 0.122 Uiso 1 1 calc R . . C9R C 0.9407(13) 0.4606(8) 0.4328(6) 0.090(4) Uani 1 1 d . . . H9R1 H 1.0378 0.4488 0.4401 0.108 Uiso 1 1 calc R . . H9R2 H 0.8972 0.4522 0.4812 0.108 Uiso 1 1 calc R . . C8R C 0.9081(10) 0.2929(9) 0.4374(6) 0.057(3) Uani 1 1 d . . . N8R N 0.8776(9) 0.2335(6) 0.4032(5) 0.068(3) Uani 1 1 d . . . H8R1 H 0.8482 0.2577 0.3579 0.082 Uiso 1 1 calc R . . C7R C 1.0084(12) 0.1788(9) 0.5403(6) 0.062(3) Uani 1 1 d . . . N7R N 1.0896(9) 0.1346(6) 0.5043(5) 0.082(3) Uani 1 1 d . . . H7R1 H 1.0996 0.161 0.4562 0.098 Uiso 1 1 calc R . . H7R2 H 1.1335 0.0788 0.5283 0.098 Uiso 1 1 calc R . . N3R N 0.8943(9) 0.3892(7) 0.4032(5) 0.074(3) Uani 1 1 d . . . H3R2 H 0.9345 0.4013 0.3576 0.089 Uiso 1 1 calc R . . N2R N 0.9385(9) 0.2622(6) 0.5093(5) 0.067(3) Uani 1 1 d . . . H2R1 H 0.9834 0.3103 0.5164 0.08 Uiso 1 1 calc R . . N1R N 1.0088(8) 0.1331(6) 0.6152(4) 0.064(3) Uani 1 1 d . . . H1R2 H 0.9899 0.0699 0.6227 0.077 Uiso 1 1 calc R . . C6R C 0.7756(11) 0.2513(9) 0.7199(6) 0.077(4) Uani 1 1 d . . . H6R H 0.7148 0.307 0.7118 0.093 Uiso 1 1 calc R . . C5R C 0.8353(12) 0.2349(9) 0.6612(6) 0.076(4) Uani 1 1 d . . . H5R H 0.8103 0.2753 0.6129 0.091 Uiso 1 1 calc R . . C4R C 0.9331(11) 0.1593(9) 0.6710(6) 0.061(3) Uani 1 1 d . . . C3R C 0.9590(11) 0.0986(8) 0.7432(6) 0.078(4) Uani 1 1 d . . . H3R H 1.0199 0.0428 0.7518 0.093 Uiso 1 1 calc R . . C2R C 0.8989(12) 0.1176(10) 0.8013(7) 0.089(4) Uani 1 1 d . . . H2R H 0.926 0.08 0.8498 0.107 Uiso 1 1 calc R . . C1R C 0.7990(12) 0.1910(9) 0.7904(6) 0.067(3) Uani 1 1 d . . . Cl1R Cl 0.7208(3) 0.2162(2) 0.86415(16) 0.0914(12) Uani 1 1 d . . . O1W O 0.1426(8) 0.1053(6) 0.3260(5) 0.093(3) Uani 1 1 d D . . H1W1 H 0.160(9) 0.161(5) 0.326(7) 0.111 Uiso 1 1 d D . . H2W1 H 0.051(3) 0.107(7) 0.338(6) 0.111 Uiso 1 1 d 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 O1A 0.029(4) 0.074(5) 0.034(4) -0.003(3) -0.004(3) -0.010(3) C1A 0.033(6) 0.054(8) 0.046(6) -0.008(6) 0.001(5) -0.005(5) C2A 0.042(6) 0.065(8) 0.035(6) -0.014(6) 0.007(5) -0.011(6) C3A 0.039(6) 0.055(8) 0.042(6) -0.009(6) 0.006(5) -0.012(5) C4A 0.032(6) 0.056(7) 0.048(6) -0.004(6) 0.004(5) -0.021(5) C5A 0.040(6) 0.052(8) 0.037(6) -0.003(5) -0.004(5) -0.016(5) C6A 0.036(6) 0.045(7) 0.033(6) -0.003(5) -0.010(5) -0.009(5) C7A 0.052(8) 0.114(10) 0.034(6) 0.008(6) -0.016(6) -0.013(7) C8A 0.040(8) 0.193(18) 0.036(8) 0.001(9) -0.008(6) -0.009(9) O9A 0.127(10) 0.324(17) 0.057(7) 0.035(8) -0.041(6) -0.079(10) O10A 0.234(12) 0.077(7) 0.043(5) 0.008(5) 0.015(6) -0.029(7) C1AB 0.049(7) 0.081(9) 0.041(6) -0.016(6) 0.010(5) -0.029(6) O1B 0.027(4) 0.056(5) 0.056(4) -0.002(4) 0.003(3) -0.002(3) C1B 0.059(7) 0.043(7) 0.043(6) -0.009(5) 0.000(6) 0.003(6) C2B 0.094(10) 0.050(8) 0.045(7) -0.021(6) 0.015(7) -0.027(8) C3B 0.071(8) 0.045(8) 0.069(8) -0.014(6) 0.017(7) 0.011(7) C4B 0.050(7) 0.051(8) 0.071(8) -0.004(6) 0.009(6) 0.007(6) C5B 0.031(6) 0.054(8) 0.049(6) -0.011(5) 0.018(5) -0.011(5) C6B 0.061(7) 0.030(7) 0.032(6) -0.009(5) 0.007(5) 0.001(6) C1BC 0.032(6) 0.059(7) 0.044(6) -0.006(6) 0.014(5) -0.003(5) O1C 0.042(4) 0.043(4) 0.043(4) -0.002(3) 0.002(3) -0.013(3) C1C 0.028(6) 0.046(7) 0.040(6) 0.000(5) 0.006(5) -0.007(5) C2C 0.041(6) 0.054(8) 0.049(7) 0.003(6) 0.005(6) -0.005(5) C3C 0.040(7) 0.061(8) 0.043(7) -0.010(6) -0.006(5) -0.010(6) C4C 0.050(7) 0.068(8) 0.033(6) -0.002(6) -0.006(5) -0.017(6) C5C 0.034(6) 0.054(8) 0.038(6) -0.002(6) -0.005(5) -0.012(5) C6C 0.042(6) 0.057(8) 0.024(6) 0.006(6) -0.017(5) -0.005(6) C7C 0.070(8) 0.045(7) 0.048(6) 0.008(5) 0.013(6) 0.001(6) C8C 0.068(9) 0.044(8) 0.060(8) -0.008(6) 0.003(7) -0.007(7) O9C 0.061(5) 0.076(6) 0.059(5) 0.009(4) 0.008(4) 0.013(4) O10C 0.088(6) 0.073(5) 0.046(4) 0.018(4) 0.016(4) 0.000(4) C1CD 0.044(6) 0.047(7) 0.057(7) -0.014(5) 0.002(5) -0.014(6) O1D 0.037(4) 0.074(5) 0.047(4) -0.022(4) 0.004(3) -0.010(4) C1D 0.049(7) 0.042(7) 0.047(7) -0.009(5) 0.001(6) -0.003(6) C2D 0.064(8) 0.046(7) 0.057(7) -0.012(6) -0.003(6) -0.012(6) C3D 0.065(8) 0.065(8) 0.057(7) -0.023(6) 0.013(7) -0.003(7) C4D 0.049(7) 0.058(8) 0.050(7) -0.007(6) 0.013(6) 0.008(6) C5D 0.043(6) 0.036(7) 0.046(6) 0.005(5) -0.001(6) -0.005(5) C6D 0.043(7) 0.057(8) 0.042(7) 0.001(6) 0.008(6) 0.006(6) C1DA 0.044(6) 0.057(8) 0.041(6) -0.010(5) -0.003(5) -0.003(6) Cl1P 0.091(2) 0.090(2) 0.0627(19) -0.0329(17) 0.0198(17) -0.0126(19) C1P 0.064(8) 0.040(7) 0.054(7) -0.004(6) -0.004(6) -0.007(6) C2P 0.082(9) 0.061(8) 0.051(7) -0.019(6) -0.005(7) 0.007(7) C3P 0.055(7) 0.068(8) 0.049(7) -0.021(6) -0.009(6) -0.002(6) C4P 0.062(8) 0.045(7) 0.046(7) -0.010(6) -0.002(6) -0.001(6) C5P 0.062(8) 0.086(10) 0.040(7) -0.006(6) -0.006(6) 0.022(7) C6P 0.069(8) 0.051(8) 0.072(8) -0.015(7) -0.006(7) 0.004(6) N1P 0.082(7) 0.047(6) 0.044(5) -0.003(5) -0.010(5) 0.017(5) N2P 0.098(8) 0.051(7) 0.046(6) -0.019(5) -0.009(5) 0.001(6) N3P 0.095(8) 0.064(8) 0.057(6) -0.009(6) -0.023(5) 0.004(6) C7P 0.073(8) 0.036(7) 0.045(7) -0.002(6) 0.002(6) 0.001(6) N7P 0.088(7) 0.084(8) 0.057(6) -0.017(6) -0.001(6) 0.019(6) C8P 0.039(7) 0.070(10) 0.055(8) -0.004(7) 0.003(6) -0.004(6) N8P 0.077(7) 0.056(7) 0.072(7) -0.020(5) -0.002(5) -0.012(5) C9P 0.146(13) 0.079(10) 0.090(10) -0.029(9) -0.022(10) -0.052(10) C10P 0.136(14) 0.078(11) 0.113(13) -0.021(9) -0.033(11) 0.008(10) C11P 0.169(16) 0.094(12) 0.075(10) -0.036(9) -0.021(11) -0.014(11) C11R 0.157(15) 0.105(13) 0.069(10) -0.029(9) -0.009(11) -0.002(12) C10R 0.199(17) 0.054(9) 0.057(9) -0.023(7) -0.009(10) -0.014(10) C9R 0.145(13) 0.060(9) 0.057(8) -0.009(7) -0.024(8) 0.000(8) C8R 0.061(8) 0.050(8) 0.040(7) 0.008(6) -0.008(6) 0.012(6) N8R 0.098(8) 0.060(7) 0.058(6) -0.035(6) -0.012(5) -0.005(6) C7R 0.081(9) 0.053(9) 0.043(7) -0.004(6) -0.011(6) -0.005(7) N7R 0.109(8) 0.067(7) 0.049(6) -0.005(5) -0.007(6) 0.040(6) N3R 0.119(9) 0.059(7) 0.047(6) -0.025(6) 0.003(5) -0.004(6) N2R 0.110(8) 0.035(6) 0.048(6) -0.007(5) -0.019(5) 0.006(6) N1R 0.077(7) 0.061(6) 0.043(6) -0.005(5) 0.001(5) -0.008(5) C6R 0.073(9) 0.089(10) 0.064(8) -0.022(8) -0.003(7) 0.011(7) C5R 0.086(9) 0.078(9) 0.047(7) -0.006(7) -0.001(7) 0.021(7) C4R 0.069(8) 0.070(9) 0.049(7) -0.025(7) -0.016(6) 0.001(7) C3R 0.084(9) 0.079(9) 0.057(8) -0.012(7) 0.004(7) 0.016(7) C2R 0.076(9) 0.121(12) 0.070(9) -0.037(8) -0.029(7) 0.026(9) C1R 0.075(9) 0.083(10) 0.042(7) -0.019(7) 0.000(6) -0.008(7) Cl1R 0.097(3) 0.115(3) 0.068(2) -0.039(2) 0.0125(19) -0.018(2) O1W 0.078(6) 0.091(7) 0.099(6) -0.026(6) -0.019(5) 0.026(5) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 O1A C6A 1.419(9) . ? O1A C7A 1.422(10) . ? C1A C6A 1.389(12) . ? C1A C2A 1.398(11) . ? C1A C1DA 1.521(12) . ? C2A C3A 1.403(12) . ? C2A H2A 0.95 . ? C3A C4A 1.378(12) . ? C3A H3A 0.95 . ? C4A C5A 1.390(11) . ? C4A H4A 0.95 . ? C5A C6A 1.383(12) . ? C5A C1AB 1.505(12) . ? C7A C8A 1.496(13) . ? C7A H7A1 0.99 . ? C7A H7A2 0.99 . ? C8A O10A 1.190(15) . ? C8A O9A 1.310(17) . ? C1AB C1B 1.527(12) . ? C1AB H1A1 0.99 . ? C1AB H1A2 0.99 . ? O1B C6B 1.409(10) . ? O1B H1B 0.84 . ? C1B C6B 1.358(12) . ? C1B C2B 1.392(13) . ? C2B C3B 1.356(13) . ? C2B H2B 0.95 . ? C3B C4B 1.396(12) . ? C3B H3B 0.95 . ? C4B C5B 1.380(12) . ? C4B H4B 0.95 . ? C5B C6B 1.405(12) . ? C5B C1BC 1.501(11) . ? C1BC C1C 1.534(12) . ? C1BC H1B1 0.99 . ? C1BC H1B2 0.99 . ? O1C C6C 1.422(10) . ? O1C C7C 1.432(9) . ? C1C C2C 1.394(12) . ? C1C C6C 1.406(12) . ? C2C C3C 1.386(12) . ? C2C H2C 0.95 . ? C3C C4C 1.370(12) . ? C3C H3C 0.95 . ? C4C C5C 1.404(12) . ? C4C H4C 0.95 . ? C5C C6C 1.383(13) . ? C5C C1CD 1.500(12) . ? C7C C8C 1.499(13) . ? C7C H7C1 0.99 . ? C7C H7C2 0.99 . ? C8C O9C 1.227(11) . ? C8C O10C 1.271(10) . ? C1CD C1D 1.504(11) . ? C1CD H1C1 0.99 . ? C1CD H1C2 0.99 . ? O1D C6D 1.366(11) . ? O1D H1D 0.84 . ? C1D C6D 1.392(13) . ? C1D C2D 1.395(12) . ? C2D C3D 1.356(12) . ? C2D H2D 0.95 . ? C3D C4D 1.397(13) . ? C3D H3D 0.95 . ? C4D C5D 1.387(13) . ? C4D H4D 0.95 . ? C5D C6D 1.407(11) . ? C5D C1DA 1.524(12) . ? C1DA H1D1 0.99 . ? C1DA H1D2 0.99 . ? Cl1P C1P 1.764(10) . ? C1P C6P 1.344(13) . ? C1P C2P 1.374(13) . ? C2P C3P 1.364(12) . ? C2P H2P 0.95 . ? C3P C4P 1.388(12) . ? C3P H3P 0.95 . ? C4P C5P 1.365(13) . ? C4P N1P 1.431(11) . ? C5P C6P 1.369(13) . ? C5P H5P 0.95 . ? C6P H6P 0.95 . ? N1P C7P 1.359(11) . ? N1P H1P1 0.92 . ? N1P H1P2 0.92 . ? N2P C7P 1.292(12) . ? N2P C8P 1.328(12) . ? N2P H2P2 0.92 . ? N3P C8P 1.343(12) . ? N3P C9P 1.478(13) . ? N3P H3P2 0.92 . ? C7P N7P 1.327(12) . ? N7P H7P1 0.88 . ? N7P H7P2 0.88 . ? C8P N8P 1.347(13) . ? N8P H8P1 0.88 . ? C9P C10P 1.526(16) . ? C9P H9P1 0.99 . ? C9P H9P2 0.99 . ? C10P C11P 1.590(17) . ? C10P H10A 0.99 . ? C10P H10B 0.99 . ? C11P C11R 1.501(15) . ? C11P H11A 0.99 . ? C11P H11B 0.99 . ? C11R C10R 1.503(16) . ? C11R H11C 0.99 . ? C11R H11D 0.99 . ? C10R C9R 1.563(14) . ? C10R H10R 0.99 . ? C10R H10P 0.99 . ? C9R N3R 1.472(13) . ? C9R H9R1 0.99 . ? C9R H9R2 0.99 . ? C8R N8R 1.323(13) . ? C8R N3R 1.331(12) . ? C8R N2R 1.350(12) . ? N8R H8R1 0.88 . ? C7R N2R 1.316(12) . ? C7R N7R 1.322(12) . ? C7R N1R 1.372(11) . ? N7R H7R1 0.88 . ? N7R H7R2 0.88 . ? N3R H3R2 0.92 . ? N2R H2R1 0.92 . ? N1R C4R 1.436(12) . ? N1R H1R2 0.92 . ? C6R C5R 1.348(13) . ? C6R C1R 1.364(13) . ? C6R H6R 0.95 . ? C5R C4R 1.386(13) . ? C5R H5R 0.95 . ? C4R C3R 1.395(13) . ? C3R C2R 1.356(14) . ? C3R H3R 0.95 . ? C2R C1R 1.378(14) . ? C2R H2R 0.95 . ? C1R Cl1R 1.736(10) . ? O1W H1W1 0.85(2) . ? O1W H2W1 0.946(19) . ? 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 C6A O1A C7A 109.8(6) . . ? C6A C1A C2A 117.0(10) . . ? C6A C1A C1DA 123.6(8) . . ? C2A C1A C1DA 119.4(9) . . ? C1A C2A C3A 120.2(9) . . ? C1A C2A H2A 119.9 . . ? C3A C2A H2A 119.9 . . ? C4A C3A C2A 120.3(9) . . ? C4A C3A H3A 119.9 . . ? C2A C3A H3A 119.9 . . ? C3A C4A C5A 121.0(10) . . ? C3A C4A H4A 119.5 . . ? C5A C4A H4A 119.5 . . ? C6A C5A C4A 117.3(9) . . ? C6A C5A C1AB 120.4(8) . . ? C4A C5A C1AB 122.3(10) . . ? C5A C6A C1A 124.1(9) . . ? C5A C6A O1A 118.8(9) . . ? C1A C6A O1A 117.1(9) . . ? O1A C7A C8A 112.6(9) . . ? O1A C7A H7A1 109.1 . . ? C8A C7A H7A1 109.1 . . ? O1A C7A H7A2 109.1 . . ? C8A C7A H7A2 109.1 . . ? H7A1 C7A H7A2 107.8 . . ? O10A C8A O9A 122.8(12) . . ? O10A C8A C7A 124.2(14) . . ? O9A C8A C7A 112.8(14) . . ? C5A C1AB C1B 113.5(8) . . ? C5A C1AB H1A1 108.9 . . ? C1B C1AB H1A1 108.9 . . ? C5A C1AB H1A2 108.9 . . ? C1B C1AB H1A2 108.9 . . ? H1A1 C1AB H1A2 107.7 . . ? C6B O1B H1B 109.5 . . ? C6B C1B C2B 116.8(9) . . ? C6B C1B C1AB 122.0(10) . . ? C2B C1B C1AB 121.2(9) . . ? C3B C2B C1B 122.3(9) . . ? C3B C2B H2B 118.9 . . ? C1B C2B H2B 118.9 . . ? C2B C3B C4B 120.4(10) . . ? C2B C3B H3B 119.8 . . ? C4B C3B H3B 119.8 . . ? C5B C4B C3B 119.0(9) . . ? C5B C4B H4B 120.5 . . ? C3B C4B H4B 120.5 . . ? C4B C5B C6B 118.6(8) . . ? C4B C5B C1BC 121.3(8) . . ? C6B C5B C1BC 120.1(9) . . ? C1B C6B C5B 122.9(9) . . ? C1B C6B O1B 122.6(9) . . ? C5B C6B O1B 114.5(8) . . ? C5B C1BC C1C 110.2(7) . . ? C5B C1BC H1B1 109.6 . . ? C1C C1BC H1B1 109.6 . . ? C5B C1BC H1B2 109.6 . . ? C1C C1BC H1B2 109.6 . . ? H1B1 C1BC H1B2 108.1 . . ? C6C O1C C7C 115.5(7) . . ? C2C C1C C6C 115.2(10) . . ? C2C C1C C1BC 122.3(10) . . ? C6C C1C C1BC 122.3(9) . . ? C3C C2C C1C 121.2(10) . . ? C3C C2C H2C 119.4 . . ? C1C C2C H2C 119.4 . . ? C4C C3C C2C 120.7(10) . . ? C4C C3C H3C 119.7 . . ? C2C C3C H3C 119.7 . . ? C3C C4C C5C 121.6(11) . . ? C3C C4C H4C 119.2 . . ? C5C C4C H4C 119.2 . . ? C6C C5C C4C 115.2(10) . . ? C6C C5C C1CD 124.2(10) . . ? C4C C5C C1CD 120.4(10) . . ? C5C C6C C1C 125.9(9) . . ? C5C C6C O1C 117.2(10) . . ? C1C C6C O1C 116.8(9) . . ? O1C C7C C8C 109.1(8) . . ? O1C C7C H7C1 109.9 . . ? C8C C7C H7C1 109.9 . . ? O1C C7C H7C2 109.9 . . ? C8C C7C H7C2 109.9 . . ? H7C1 C7C H7C2 108.3 . . ? O9C C8C O10C 124.8(10) . . ? O9C C8C C7C 121.1(9) . . ? O10C C8C C7C 114.0(9) . . ? C5C C1CD C1D 114.6(7) . . ? C5C C1CD H1C1 108.6 . . ? C1D C1CD H1C1 108.6 . . ? C5C C1CD H1C2 108.6 . . ? C1D C1CD H1C2 108.6 . . ? H1C1 C1CD H1C2 107.6 . . ? C6D O1D H1D 109.5 . . ? C6D C1D C2D 117.2(9) . . ? C6D C1D C1CD 122.7(9) . . ? C2D C1D C1CD 120.0(10) . . ? C3D C2D C1D 123.0(10) . . ? C3D C2D H2D 118.5 . . ? C1D C2D H2D 118.5 . . ? C2D C3D C4D 118.0(10) . . ? C2D C3D H3D 121 . . ? C4D C3D H3D 121 . . ? C5D C4D C3D 122.9(10) . . ? C5D C4D H4D 118.6 . . ? C3D C4D H4D 118.6 . . ? C4D C5D C6D 116.4(10) . . ? C4D C5D C1DA 122.5(9) . . ? C6D C5D C1DA 121.1(10) . . ? O1D C6D C1D 122.6(9) . . ? O1D C6D C5D 114.9(10) . . ? C1D C6D C5D 122.4(10) . . ? C1A C1DA C5D 113.1(8) . . ? C1A C1DA H1D1 109 . . ? C5D C1DA H1D1 109 . . ? C1A C1DA H1D2 109 . . ? C5D C1DA H1D2 109 . . ? H1D1 C1DA H1D2 107.8 . . ? C6P C1P C2P 122.4(10) . . ? C6P C1P Cl1P 118.9(9) . . ? C2P C1P Cl1P 118.7(9) . . ? C3P C2P C1P 116.4(10) . . ? C3P C2P H2P 121.8 . . ? C1P C2P H2P 121.8 . . ? C2P C3P C4P 122.3(11) . . ? C2P C3P H3P 118.9 . . ? C4P C3P H3P 118.9 . . ? C5P C4P C3P 119.4(10) . . ? C5P C4P N1P 126.1(10) . . ? C3P C4P N1P 114.5(10) . . ? C4P C5P C6P 118.6(10) . . ? C4P C5P H5P 120.7 . . ? C6P C5P H5P 120.7 . . ? C1P C6P C5P 120.9(11) . . ? C1P C6P H6P 119.5 . . ? C5P C6P H6P 119.5 . . ? C7P N1P C4P 127.9(9) . . ? C7P N1P H1P1 105.3 . . ? C4P N1P H1P1 105.3 . . ? C7P N1P H1P2 105.3 . . ? C4P N1P H1P2 105.3 . . ? H1P1 N1P H1P2 106 . . ? C7P N2P C8P 126.6(10) . . ? C7P N2P H2P2 105.7 . . ? C8P N2P H2P2 105.7 . . ? C8P N3P C9P 122.5(11) . . ? C8P N3P H3P2 106.7 . . ? C9P N3P H3P2 106.7 . . ? N2P C7P N7P 124.4(10) . . ? N2P C7P N1P 119.4(10) . . ? N7P C7P N1P 115.6(10) . . ? C7P N7P H7P1 120 . . ? C7P N7P H7P2 120 . . ? H7P1 N7P H7P2 120 . . ? N2P C8P N3P 119.7(12) . . ? N2P C8P N8P 122.8(12) . . ? N3P C8P N8P 117.5(11) . . ? C8P N8P H8P1 120 . . ? N3P C9P C10P 110.7(10) . . ? N3P C9P H9P1 109.5 . . ? C10P C9P H9P1 109.5 . . ? N3P C9P H9P2 109.5 . . ? C10P C9P H9P2 109.5 . . ? H9P1 C9P H9P2 108.1 . . ? C9P C10P C11P 116.1(12) . . ? C9P C10P H10A 108.3 . . ? C11P C10P H10A 108.3 . . ? C9P C10P H10B 108.3 . . ? C11P C10P H10B 108.3 . . ? H10A C10P H10B 107.4 . . ? C11R C11P C10P 112.6(13) . . ? C11R C11P H11A 109.1 . . ? C10P C11P H11A 109.1 . . ? C11R C11P H11B 109.1 . . ? C10P C11P H11B 109.1 . . ? H11A C11P H11B 107.8 . . ? C11P C11R C10R 113.4(13) . . ? C11P C11R H11C 108.9 . . ? C10R C11R H11C 108.9 . . ? C11P C11R H11D 108.9 . . ? C10R C11R H11D 108.9 . . ? H11C C11R H11D 107.7 . . ? C11R C10R C9R 112.9(12) . . ? C11R C10R H10R 109 . . ? C9R C10R H10R 109 . . ? C11R C10R H10P 109 . . ? C9R C10R H10P 109 . . ? H10R C10R H10P 107.8 . . ? N3R C9R C10R 110.7(10) . . ? N3R C9R H9R1 109.5 . . ? C10R C9R H9R1 109.5 . . ? N3R C9R H9R2 109.5 . . ? C10R C9R H9R2 109.5 . . ? H9R1 C9R H9R2 108.1 . . ? N8R C8R N3R 119.9(11) . . ? N8R C8R N2R 123.4(10) . . ? N3R C8R N2R 116.2(12) . . ? C8R N8R H8R1 120 . . ? N2R C7R N7R 124.5(10) . . ? N2R C7R N1R 121.5(11) . . ? N7R C7R N1R 113.8(10) . . ? C7R N7R H7R1 120 . . ? C7R N7R H7R2 120 . . ? H7R1 N7R H7R2 120 . . ? C8R N3R C9R 123.9(10) . . ? C8R N3R H3R2 106.4 . . ? C9R N3R H3R2 106.4 . . ? C7R N2R C8R 120.9(10) . . ? C7R N2R H2R1 107.1 . . ? C8R N2R H2R1 107.1 . . ? C7R N1R C4R 129.2(10) . . ? C7R N1R H1R2 105 . . ? C4R N1R H1R2 105 . . ? C5R C6R C1R 122.6(12) . . ? C5R C6R H6R 118.7 . . ? C1R C6R H6R 118.7 . . ? C6R C5R C4R 120.3(11) . . ? C6R C5R H5R 119.9 . . ? C4R C5R H5R 119.9 . . ? C5R C4R C3R 117.1(10) . . ? C5R C4R N1R 127.7(10) . . ? C3R C4R N1R 115.2(11) . . ? C2R C3R C4R 121.2(12) . . ? C2R C3R H3R 119.4 . . ? C4R C3R H3R 119.4 . . ? C3R C2R C1R 120.6(12) . . ? C3R C2R H2R 119.7 . . ? C1R C2R H2R 119.7 . . ? C6R C1R C2R 117.5(11) . . ? C6R C1R Cl1R 120.8(10) . . ? C2R C1R Cl1R 121.2(10) . . ? H1W1 O1W H2W1 100(4) . . ? 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 C4P N1P C7P N2P -15.5(16) . . . . ? N1P C7P N2P C8P 165.1(10) . . . . ? C7P N2P C8P N3P 135.6(12) . . . . ? N2P C8P N3P C9P -5.7(16) . . . . ? C8P N3P C9P C10P 74.5(15) . . . . ? N3P C9P C10P C11P 52.1(15) . . . . ? C9P C10P C11P C11R 177.4(11) . . . . ? C10P C11P C11R C10R 176.9(11) . . . . ? C11P C11R C10R C9R 71.5(15) . . . . ? C11R C10R C9R N3R 61.5(14) . . . . ? C10R C9R N3R C8R -179.6(10) . . . . ? N3R C8R N2R C7R -150.3(10) . . . . ? C8R N2R C7R N1R -161.3(10) . . . . ? N2R C7R N1R C4R 4.6(17) . . . . ? # Attachment 'C4diP-chlorhex.cif' data_Calix[4]diPhosphateChlorhexidine _database_code_depnum_ccdc_archive 'CCDC 661949' _audit_creation_method SHELXL-97 #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; 'calix[4]arene dihydroxyphosphonic acid Chlorhexidine' ; _chemical_name_common "'calix(4)arene dihydroxyphosphonic acid Chlorhexidine'" _chemical_formula_moiety '2(C22 H30 Cl2 N10), 6(C H4 O), 6(H2 O), 2(C59 H142 K2 O28 P4)' _chemical_formula_sum 'C168 H230 Cl4 K4 N20 O69 P8' _chemical_formula_weight 4179.68 _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# loop_ _space_group_symop_operation_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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C c' _symmetry_space_group_name_Hall 'C -2yc' _cell_length_a 26.4440(13) _cell_length_b 13.1260(16) _cell_length_c 31.572(3) _cell_angle_alpha 90.000(5) _cell_angle_beta 109.506(6) _cell_angle_gamma 90.000(6) _cell_volume 10329.8(17) _cell_formula_units_Z 2 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 12557 _cell_measurement_theta_min 2.68 _cell_measurement_theta_max 18.9 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description parallepiped _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 1.344 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4388 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.288 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method rotation _diffrn_detector_area_resol_mean 9.1 _diffrn_reflns_av_R_equivalents 0.0632 _diffrn_reflns_av_unetI/netI 0.0985 _diffrn_reflns_number 12617 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.68 _diffrn_reflns_theta_max 18.9 _diffrn_reflns_theta_full 18.9 _diffrn_measured_fraction_theta_full 0.983 _diffrn_measured_fraction_theta_max 0.983 _reflns_number_total 7656 _reflns_number_gt 5493 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect data collection software (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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.Restraints were used to fix solvent geometries : distances and angles. ; _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^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 7656 _refine_ls_number_parameters 853 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.1038 _refine_ls_R_factor_gt 0.0714 _refine_ls_wR_factor_ref 0.1879 _refine_ls_wR_factor_gt 0.1695 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.006 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.48(9) _refine_diff_density_max 0.522 _refine_diff_density_min -0.288 _refine_diff_density_rms 0.074 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' K K 0.2009 0.2494 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 O1W O 0.2074(4) 0.2794(7) 0.3963(3) 0.081(3) Uiso 1 1 d . . . O2W O 0.0622(7) 0.7546(11) 0.4225(5) 0.053(4) Uiso 0.5 1 d P . . O3W O 0.4830(6) 0.3814(10) 0.2827(5) 0.086(4) Uiso 0.7 1 d P A 1 O3W' O 0.5103(15) 0.248(3) 0.2656(12) 0.094(11) Uiso 0.3 1 d P B 2 O4W O 0.9777(13) 0.558(2) 0.3763(11) 0.073(9) Uiso 0.3 1 d P C 1 O4W' O 0.976(2) 0.555(4) 0.336(2) 0.097(17) Uiso 0.2 1 d P D 2 O5W O 0.9783(12) 0.753(2) 0.4464(10) 0.084(8) Uiso 0.35 1 d P E 1 O5W' O 1.027(3) 0.682(5) 0.500(2) 0.08(2) Uiso 0.15 1 d P F 2 Cl3R Cl 0.94443(18) 0.8768(4) 0.15461(14) 0.1012(16) Uani 1 1 d . . . C5R C 0.8622(6) 0.8998(14) 0.0240(6) 0.063(4) Uani 1 1 d . . . H5R H 0.8535 0.9521 0.0019 0.076 Uiso 1 1 calc R . . C4R C 0.8940(6) 0.9224(13) 0.0662(6) 0.058(4) Uani 1 1 d . . . H4R H 0.9086 0.9888 0.0732 0.07 Uiso 1 1 calc R . . C3R C 0.9048(6) 0.8490(17) 0.0987(5) 0.068(5) Uani 1 1 d . . . C2R C 0.8835(7) 0.7518(14) 0.0897(6) 0.068(4) Uani 1 1 d . . . H2R H 0.8904 0.7026 0.113 0.082 Uiso 1 1 calc R . . C1R C 0.8518(6) 0.7273(11) 0.0459(6) 0.060(4) Uani 1 1 d . . . H1R H 0.8372 0.6607 0.0393 0.072 Uiso 1 1 calc R . . C6R C 0.8412(7) 0.7997(13) 0.0113(7) 0.064(5) Uani 1 1 d . . . N7R N 0.8050(5) 0.7697(9) -0.0298(4) 0.059(3) Uani 1 1 d . . . H7R1 H 0.8138 0.7031 -0.0332 0.071 Uiso 1 1 calc R . . C8R C 0.7942(8) 0.8126(14) -0.0717(6) 0.068(5) Uani 1 1 d . . . N8R N 0.7578(5) 0.7682(9) -0.1058(4) 0.064(3) Uani 1 1 d . . . H8R1 H 0.7491 0.7949 -0.1329 0.077 Uiso 0.5 1 calc PR . . H8R2 H 0.7422 0.7117 -0.1016 0.077 Uiso 0.5 1 calc PR . . N9R N 0.8205(5) 0.8986(12) -0.0742(4) 0.064(3) Uani 1 1 d . . . C10R C 0.8015(9) 0.9598(12) -0.1118(6) 0.068(5) Uani 1 1 d . . . N10R N 0.7503(6) 0.9846(8) -0.1317(4) 0.062(3) Uani 1 1 d . . . H10A H 0.7414 1.0305 -0.1532 0.075 Uiso 1 1 calc R . . H10B H 0.7253 0.9551 -0.1233 0.075 Uiso 1 1 calc R . . N11R N 0.8385(6) 1.0064(9) -0.1255(4) 0.078(4) Uani 1 1 d . . . H11A H 0.8324 1.0752 -0.1245 0.093 Uiso 1 1 calc R . . C6Y C 0.8982(8) 0.9919(14) -0.1040(6) 0.088(6) Uani 1 1 d D . . H6Y1 H 0.9046 0.9604 -0.0742 0.105 Uiso 1 1 calc R . . H6Y2 H 0.9149 1.0603 -0.0987 0.105 Uiso 1 1 calc R . . C5Y C 0.9281(13) 0.928(2) -0.1287(8) 0.27(2) Uani 1 1 d D . . H5Y1 H 0.9303 0.9661 -0.1551 0.324 Uiso 1 1 calc R . . H5Y2 H 0.9651 0.9142 -0.1085 0.324 Uiso 1 1 calc R . . C4Y C 0.8990(11) 0.832(2) -0.1432(10) 0.178(12) Uani 1 1 d D . . H4Y1 H 0.8609 0.8493 -0.159 0.214 Uiso 1 1 calc R . . H4Y2 H 0.9002 0.7943 -0.1156 0.214 Uiso 1 1 calc R . . C3Y C 0.9162(12) 0.756(3) -0.1735(13) 0.29(2) Uani 1 1 d D . . H3Y1 H 0.9114 0.6861 -0.164 0.342 Uiso 1 1 calc R . . H3Y2 H 0.8918 0.765 -0.2048 0.342 Uiso 1 1 calc R . . C2Y C 0.9731(10) 0.7682(18) -0.1727(11) 0.204(16) Uani 1 1 d D . . H2Y1 H 0.9968 0.7537 -0.1417 0.245 Uiso 1 1 calc R . . H2Y2 H 0.9782 0.8408 -0.1786 0.245 Uiso 1 1 calc R . . C1Y C 0.9936(9) 0.7051(19) -0.2044(8) 0.165(11) Uani 1 1 d D . . H1Y1 H 0.9883 0.632 -0.1994 0.198 Uiso 1 1 calc R . . H1Y2 H 0.9718 0.7216 -0.2358 0.198 Uiso 1 1 calc R . . N11X N 1.0477(7) 0.7210(11) -0.1990(5) 0.093(4) Uani 1 1 d . . . H11D H 1.0648 0.7281 -0.1686 0.111 Uiso 1 1 calc R . . C10X C 1.0784(9) 0.6639(14) -0.2126(5) 0.072(5) Uani 1 1 d . . . N10X N 1.1293(7) 0.6914(9) -0.2041(4) 0.078(4) Uani 1 1 d . . . H10C H 1.1414 0.7481 -0.1894 0.094 Uiso 1 1 calc R . . H10D H 1.1508 0.6528 -0.2133 0.094 Uiso 1 1 calc R . . N9X N 1.0548(5) 0.5814(13) -0.2402(4) 0.076(4) Uani 1 1 d . . . C8X C 1.0818(7) 0.4987(15) -0.2399(6) 0.059(4) Uani 1 1 d . . . N8X N 1.1206(6) 0.4657(9) -0.2037(5) 0.068(4) Uani 1 1 d . . . H8X1 H 1.1291 0.5005 -0.1784 0.082 Uiso 0.5 1 calc PR . . H8X2 H 1.1379 0.4091 -0.2049 0.082 Uiso 0.5 1 calc PR . . N7X N 1.0727(5) 0.4396(10) -0.2751(5) 0.070(4) Uani 1 1 d . . . H7X1 H 1.0619 0.3785 -0.2667 0.084 Uiso 1 1 calc R . . C6X C 1.0377(7) 0.4556(15) -0.3208(6) 0.062(4) Uani 1 1 d . . . C1X C 1.0219(6) 0.5511(13) -0.3377(6) 0.059(4) Uani 1 1 d . . . H1X H 1.032 0.6091 -0.3188 0.07 Uiso 1 1 calc R . . C2X C 0.9898(7) 0.5628(15) -0.3845(7) 0.075(5) Uani 1 1 d . . . H2X H 0.9777 0.6278 -0.397 0.091 Uiso 1 1 calc R . . C3X C 0.9778(6) 0.4794(15) -0.4091(5) 0.061(4) Uani 1 1 d . . . C4X C 0.9959(7) 0.3849(13) -0.3929(6) 0.059(4) Uani 1 1 d . . . H4X H 0.9881 0.3274 -0.4123 0.071 Uiso 1 1 calc R . . C5X C 1.0247(7) 0.3744(12) -0.3498(7) 0.064(4) Uani 1 1 d . . . H5X H 1.0366 0.3084 -0.3385 0.077 Uiso 1 1 calc R . . Cl3X Cl 0.93948(17) 0.4912(3) -0.46569(12) 0.0790(13) Uani 1 1 d . . . K2 K 0.14250(12) 0.9817(2) 0.34801(9) 0.0515(9) Uani 1 1 d . . . K1 K 0.30943(17) 1.1037(3) 0.38735(12) 0.0883(12) Uani 1 1 d . . . P3 P 0.1797(2) 0.7951(3) 0.27723(14) 0.0633(13) Uani 1 1 d . . . O11 O 0.1857(4) 0.8661(6) 0.3154(3) 0.059(3) Uani 1 1 d . . . O12 O 0.1265(4) 0.7421(6) 0.2552(3) 0.062(3) Uani 1 1 d . . . O13 O 0.2258(4) 0.7165(6) 0.2936(3) 0.062(3) Uani 1 1 d . . . O14 O 0.1949(4) 0.8685(6) 0.2405(3) 0.056(3) Uani 1 1 d . . . P4 P 0.2682(2) 1.2880(3) 0.29985(13) 0.0629(12) Uani 1 1 d . . . O7 O 0.2591(4) 1.2158(7) 0.3347(3) 0.067(3) Uani 1 1 d . . . O8 O 0.2270(4) 1.3750(6) 0.2881(3) 0.070(3) Uani 1 1 d . . . O9 O 0.3250(4) 1.3238(7) 0.3108(3) 0.068(3) Uani 1 1 d . . . O10 O 0.2530(4) 1.2105(6) 0.2572(3) 0.058(3) Uani 1 1 d . . . O15 O 0.2840(4) 1.0068(6) 0.2501(3) 0.061(3) Uiso 1 1 d . . . H15 H 0.2803 1.0702 0.2513 0.073 Uiso 1 1 calc R . . O16 O 0.1624(4) 1.0620(6) 0.2141(3) 0.059(2) Uiso 1 1 d . . . H16 H 0.192 1.0863 0.2146 0.071 Uiso 1 1 calc R . . C73 C 0.1455(5) 0.8433(9) 0.1627(4) 0.047(3) Uiso 1 1 d . . . C74 C 0.1930(5) 0.8354(9) 0.1977(4) 0.048(4) Uiso 1 1 d . . . C75 C 0.2415(6) 0.8031(9) 0.1919(4) 0.054(4) Uiso 1 1 d . . . C76 C 0.2384(6) 0.7720(9) 0.1501(4) 0.052(4) Uiso 1 1 d . . . H76 H 0.2699 0.7476 0.1454 0.063 Uiso 1 1 calc R . . C77 C 0.1917(6) 0.7744(9) 0.1145(5) 0.055(4) Uiso 1 1 d . . . H77 H 0.1914 0.7506 0.086 0.066 Uiso 1 1 calc R . . C78 C 0.1449(6) 0.8109(9) 0.1193(4) 0.056(4) Uiso 1 1 d . . . H78 H 0.1129 0.8145 0.0942 0.067 Uiso 1 1 calc R . . C79 C 0.0950(6) 0.8971(9) 0.1655(5) 0.054(4) Uiso 1 1 d . . . H79A H 0.063 0.8593 0.1466 0.065 Uiso 1 1 calc R . . H79B H 0.0953 0.8935 0.1969 0.065 Uiso 1 1 calc R . . C80 C 0.0483(6) 1.0317(9) 0.1114(4) 0.050(4) Uiso 1 1 d . . . H80 H 0.0246 0.9807 0.0945 0.06 Uiso 1 1 calc R . . C81 C 0.1236(5) 1.0855(10) 0.1740(4) 0.050(4) Uiso 1 1 d . . . C82 C 0.0893(6) 1.0060(10) 0.1512(5) 0.055(4) Uiso 1 1 d . . . C83 C 0.0423(6) 1.1311(10) 0.0971(5) 0.059(4) Uiso 1 1 d . . . H83 H 0.0142 1.1474 0.0701 0.071 Uiso 1 1 calc R . . C84 C 0.0758(6) 1.2089(10) 0.1205(4) 0.057(4) Uiso 1 1 d . . . H84 H 0.0701 1.2768 0.1095 0.068 Uiso 1 1 calc R . . C85 C 0.1177(5) 1.1872(9) 0.1603(4) 0.044(3) Uiso 1 1 d . . . C86 C 0.2929(6) 0.8051(10) 0.2290(5) 0.067(4) Uiso 1 1 d . . . H86A H 0.3108 0.7383 0.2307 0.08 Uiso 1 1 calc R . . H86B H 0.2858 0.8152 0.2576 0.08 Uiso 1 1 calc R . . C87 C 0.3296(5) 0.8868(9) 0.2243(4) 0.048(4) Uiso 1 1 d . . . C88 C 0.3268(5) 0.9852(9) 0.2328(4) 0.045(3) Uiso 1 1 d . . . C89 C 0.3591(6) 1.0658(9) 0.2293(4) 0.053(4) Uiso 1 1 d . . . C90 C 0.3996(6) 1.0397(10) 0.2103(4) 0.060(4) Uiso 1 1 d . . . H90 H 0.4221 1.09 0.2042 0.072 Uiso 1 1 calc R . . C91 C 0.4043(7) 0.9396(11) 0.2014(5) 0.075(5) Uiso 1 1 d . . . H91 H 0.4327 0.9207 0.191 0.09 Uiso 1 1 calc R . . C92 C 0.3703(6) 0.8619(12) 0.2066(5) 0.074(4) Uiso 1 1 d . . . H92 H 0.3747 0.7938 0.1983 0.089 Uiso 1 1 calc R . . C93 C 0.2547(6) 1.2379(9) 0.2144(5) 0.053(4) Uiso 1 1 d . . . C94 C 0.2089(6) 1.2683(9) 0.1817(4) 0.048(3) Uiso 1 1 d . . . C95 C 0.2101(6) 1.2933(9) 0.1377(5) 0.061(4) Uiso 1 1 d . . . H95 H 0.1789 1.3131 0.1138 0.073 Uiso 1 1 calc R . . C96 C 0.2594(6) 1.2866(10) 0.1328(5) 0.065(4) Uiso 1 1 d . . . H96 H 0.2619 1.3092 0.1049 0.078 Uiso 1 1 calc R . . C97 C 0.3050(6) 1.2511(10) 0.1635(5) 0.066(4) Uiso 1 1 d . . . H97 H 0.3368 1.2432 0.1562 0.079 Uiso 1 1 calc R . . C98 C 0.3041(6) 1.2257(10) 0.2073(4) 0.057(4) Uiso 1 1 d . . . C99 C 0.3534(6) 1.1750(9) 0.2392(4) 0.057(4) Uiso 1 1 d . . . H99A H 0.3855 1.2123 0.2382 0.069 Uiso 1 1 calc R . . H99B H 0.3523 1.1808 0.2702 0.069 Uiso 1 1 calc R . . C100 C 0.1537(6) 1.2693(10) 0.1870(5) 0.060(4) Uiso 1 1 d . . . H10E H 0.1579 1.2606 0.2191 0.072 Uiso 1 1 calc R . . H10F H 0.1367 1.3363 0.1772 0.072 Uiso 1 1 calc R . . P1 P 0.23094(18) 0.9845(3) 0.43954(13) 0.0524(11) Uani 1 1 d . . . O17 O 0.2149(3) 1.0659(6) 0.4719(3) 0.044(2) Uani 1 1 d . . . O18 O 0.1850(4) 0.9104(6) 0.4216(3) 0.056(3) Uani 1 1 d . . . O19 O 0.2825(4) 0.9347(7) 0.4676(3) 0.065(3) Uani 1 1 d . . . O20 O 0.2355(4) 1.0473(6) 0.4011(3) 0.060(3) Uani 1 1 d . . . P2 P 0.1385(2) 1.5005(3) 0.42080(14) 0.0704(13) Uani 1 1 d . . . O21 O 0.0858(5) 1.5505(8) 0.4170(4) 0.089(3) Uani 1 1 d . . . O22 O 0.1508(4) 1.4132(6) 0.4599(3) 0.056(3) Uani 1 1 d . . . O23 O 0.1851(4) 1.5757(6) 0.4364(3) 0.059(3) Uani 1 1 d . . . O24 O 0.1429(5) 1.4442(7) 0.3820(3) 0.082(3) Uani 1 1 d . . . O25 O 0.1188(4) 1.2077(7) 0.4586(3) 0.062(3) Uiso 1 1 d . . . H25 H 0.1457 1.2311 0.4788 0.075 Uiso 1 1 calc R . . O26 O 0.2405(3) 1.2685(6) 0.5025(3) 0.052(2) Uiso 1 1 d . . . H26 H 0.2409 1.2078 0.4942 0.063 Uiso 1 1 calc R . . C51 C 0.3599(6) 1.2358(10) 0.6048(4) 0.060(4) Uiso 1 1 d . . . H51 H 0.3857 1.1865 0.6206 0.072 Uiso 1 1 calc R . . C52 C 0.3633(6) 1.3294(10) 0.6198(5) 0.061(4) Uiso 1 1 d . . . H52 H 0.392 1.346 0.6463 0.073 Uiso 1 1 calc R . . C53 C 0.3271(6) 1.4065(11) 0.5989(5) 0.062(4) Uiso 1 1 d . . . H53 H 0.3302 1.4728 0.6115 0.074 Uiso 1 1 calc R . . C54 C 0.3105(5) 1.0995(9) 0.5468(4) 0.051(4) Uiso 1 1 d . . . H54A H 0.3426 1.0595 0.5637 0.061 Uiso 1 1 calc R . . H54B H 0.3083 1.1005 0.5149 0.061 Uiso 1 1 calc R . . C27 C 0.0504(6) 1.3710(10) 0.4720(5) 0.064(4) Uiso 1 1 d . . . H27A H 0.0551 1.3782 0.4423 0.076 Uiso 1 1 calc R . . H27B H 0.0176 1.4088 0.4711 0.076 Uiso 1 1 calc R . . C28 C 0.0976(6) 1.4154(9) 0.5073(4) 0.055(4) Uiso 1 1 d . . . C29 C 0.0943(7) 1.4387(10) 0.5504(5) 0.068(4) Uiso 1 1 d . . . H29 H 0.0609 1.4317 0.5551 0.081 Uiso 1 1 calc R . . C30 C 0.1373(6) 1.4703(9) 0.5844(5) 0.055(4) Uiso 1 1 d . . . H30 H 0.1338 1.4855 0.6127 0.066 Uiso 1 1 calc R . . C31 C 0.1870(6) 1.4810(9) 0.5787(4) 0.049(4) Uiso 1 1 d . . . H31 H 0.217 1.502 0.6035 0.059 Uiso 1 1 calc R . . C32 C 0.1938(6) 1.4618(10) 0.5379(5) 0.058(4) Uiso 1 1 d . . . C33 C 0.1486(6) 1.4330(10) 0.5021(5) 0.054(4) Uiso 1 1 d . . . C34 C 0.0433(6) 1.2569(10) 0.4812(5) 0.061(4) Uiso 1 1 d . . . C35 C 0.0786(5) 1.1837(10) 0.4769(4) 0.052(4) Uiso 1 1 d . . . C36 C 0.0724(6) 1.0820(9) 0.4848(4) 0.056(4) Uiso 1 1 d . . . C37 C 0.0311(6) 1.0562(10) 0.5011(4) 0.053(4) Uiso 1 1 d . . . H37 H 0.0265 0.987 0.5077 0.064 Uiso 1 1 calc R . . C38 C -0.0020(6) 1.1257(9) 0.5075(4) 0.055(4) Uiso 1 1 d . . . H38 H -0.0292 1.1052 0.5191 0.066 Uiso 1 1 calc R . . C39 C 0.0022(6) 1.2245(10) 0.4979(4) 0.062(4) Uiso 1 1 d . . . H39 H -0.0224 1.2728 0.5024 0.074 Uiso 1 1 calc R . . C40 C 0.1692(6) 0.9745(9) 0.5631(4) 0.051(4) Uiso 1 1 d . . . H40 H 0.1374 0.9517 0.5678 0.062 Uiso 1 1 calc R . . C41 C 0.2152(6) 0.9770(9) 0.5984(5) 0.059(4) Uiso 1 1 d . . . H41 H 0.2158 0.9531 0.627 0.071 Uiso 1 1 calc R . . C42 C 0.1663(6) 1.0036(9) 0.5200(4) 0.052(4) Uiso 1 1 d . . . C43 C 0.1121(6) 1.0017(10) 0.4797(5) 0.062(4) Uiso 1 1 d . . . H43A H 0.1195 1.0142 0.4514 0.075 Uiso 1 1 calc R . . H43B H 0.0957 0.9333 0.4777 0.075 Uiso 1 1 calc R . . C44 C 0.2606(6) 1.0137(9) 0.5931(5) 0.053(4) Uiso 1 1 d . . . H44 H 0.2927 1.0173 0.6182 0.063 Uiso 1 1 calc R . . C45 C 0.2609(5) 1.0469(8) 0.5503(4) 0.041(3) Uiso 1 1 d . . . C46 C 0.2155(5) 1.0370(9) 0.5150(4) 0.046(3) Uiso 1 1 d . . . C47 C 0.3171(6) 1.2077(9) 0.5646(4) 0.048(3) Uiso 1 1 d . . . C48 C 0.2816(6) 1.2834(10) 0.5430(5) 0.059(4) Uiso 1 1 d . . . C49 C 0.2874(6) 1.3838(10) 0.5600(4) 0.052(4) Uiso 1 1 d . . . C50 C 0.2486(6) 1.4641(10) 0.5329(5) 0.059(4) Uiso 1 1 d . . . H50A H 0.2646 1.5322 0.5422 0.07 Uiso 1 1 calc R . . H50B H 0.2442 1.4551 0.5008 0.07 Uiso 1 1 calc R . . O1A O 0.0630(5) 1.0102(8) 0.2825(4) 0.095(3) Uiso 1 1 d . . . C1A C 0.0405(8) 1.0683(14) 0.2399(6) 0.114(6) Uiso 1 1 d . . . H1A1 H 0.0623 1.1293 0.2411 0.136 Uiso 1 1 calc R . . H1A2 H 0.0035 1.0886 0.2361 0.136 Uiso 1 1 calc R . . H1A3 H 0.0408 1.0255 0.2146 0.136 Uiso 1 1 calc R . . O2A O 0.3101(4) 1.2177(7) 0.4420(3) 0.086(3) Uiso 1 1 d . . . C2A C 0.3490(10) 1.2977(15) 0.4639(7) 0.140(8) Uiso 1 1 d . . . H2A1 H 0.344 1.3563 0.4437 0.168 Uiso 1 1 calc R . . H2A2 H 0.3855 1.2712 0.4708 0.168 Uiso 1 1 calc R . . H2A3 H 0.3433 1.319 0.4917 0.168 Uiso 1 1 calc R . . O3A O 0.3593(5) 0.9895(8) 0.4374(4) 0.100(3) Uiso 1 1 d . . . C3A C 0.3822(9) 0.8976(14) 0.4238(7) 0.123(7) Uiso 1 1 d . . . H3A1 H 0.3767 0.9007 0.3916 0.148 Uiso 1 1 calc R . . H3A2 H 0.3645 0.8368 0.4302 0.148 Uiso 1 1 calc R . . H3A3 H 0.4207 0.8942 0.4406 0.148 Uiso 1 1 calc R . . O1K O 0.1252(4) 1.1444(6) 0.3774(3) 0.063(3) Uiso 1 1 d . . . O2K O 0.0695(5) 0.9010(8) 0.3629(4) 0.104(4) Uiso 1 1 d . . . O3K O 0.3775(6) 1.1817(10) 0.3736(4) 0.129(4) Uiso 1 1 d . . . O4K O 0.2857(4) 0.9735(7) 0.3367(3) 0.074(3) Uiso 1 1 d . . . O5K O 0.1713(4) 1.1028(6) 0.3029(3) 0.057(2) Uiso 1 1 d . . . O1M O 0.2290(4) 0.5548(7) 0.2506(3) 0.066(3) Uiso 1 1 d . . . H1M H 0.2252 0.5031 0.2649 0.08 Uiso 1 1 calc R . . C1M C 0.1960(6) 0.5444(10) 0.2037(5) 0.067(4) Uiso 1 1 d . . . H1M1 H 0.1582 0.5545 0.2007 0.08 Uiso 1 1 calc R . . H1M2 H 0.2007 0.4762 0.1931 0.08 Uiso 1 1 calc R . . H1M3 H 0.2067 0.5957 0.1858 0.08 Uiso 1 1 calc R . . O2M O 0.1723(4) 0.2480(8) 0.9680(3) 0.081(3) Uiso 1 1 d . . . H2M H 0.1946 0.2442 0.9544 0.098 Uiso 1 1 calc R . . C2M C 0.1998(7) 0.2443(12) 1.0153(5) 0.086(5) Uiso 1 1 d . . . H2M1 H 0.2302 0.2918 1.0232 0.103 Uiso 1 1 calc R . . H2M2 H 0.2131 0.175 1.0239 0.103 Uiso 1 1 calc R . . H2M3 H 0.1752 0.2636 1.0312 0.103 Uiso 1 1 calc R . . O3M O 0.8832(5) 0.9200(8) 0.2668(4) 0.100(3) Uiso 1 1 d D . . H3M H 0.9123 0.9468 0.2823 0.12 Uiso 1 1 calc R . . C3M C 0.8545(6) 0.9882(11) 0.2333(5) 0.081(5) Uiso 1 1 d D . . H3M1 H 0.879 1.0398 0.2288 0.097 Uiso 1 1 calc R . . H3M2 H 0.8267 1.0216 0.2425 0.097 Uiso 1 1 calc R . . H3M3 H 0.8377 0.9511 0.2052 0.097 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl3R 0.063(3) 0.161(4) 0.075(3) -0.037(3) 0.017(3) 0.001(3) C5R 0.035(11) 0.097(16) 0.072(15) 0.003(10) 0.038(12) 0.012(9) C4R 0.032(10) 0.105(13) 0.042(11) -0.011(12) 0.018(10) 0.000(9) C3R 0.039(11) 0.113(15) 0.050(12) -0.027(13) 0.013(9) 0.008(11) C2R 0.070(13) 0.079(13) 0.052(13) -0.012(10) 0.014(11) 0.006(10) C1R 0.072(13) 0.065(11) 0.056(12) -0.010(10) 0.037(11) -0.013(9) C6R 0.062(13) 0.060(12) 0.093(17) 0.003(13) 0.055(13) -0.001(10) N7R 0.062(10) 0.085(9) 0.030(8) -0.004(8) 0.016(8) -0.003(8) C8R 0.090(16) 0.062(13) 0.061(15) 0.021(11) 0.035(13) 0.015(11) N8R 0.075(10) 0.067(8) 0.045(8) -0.001(7) 0.014(8) -0.009(8) N9R 0.053(9) 0.080(10) 0.051(9) 0.025(8) 0.008(8) 0.010(8) C10R 0.080(16) 0.073(12) 0.077(14) -0.014(11) 0.062(14) 0.012(12) N10R 0.048(10) 0.070(8) 0.068(9) 0.009(6) 0.017(8) -0.007(7) N11R 0.073(12) 0.075(9) 0.097(11) 0.020(7) 0.045(10) 0.028(8) C6Y 0.089(17) 0.104(14) 0.093(15) 0.027(11) 0.060(14) 0.015(11) C5Y 0.46(7) 0.26(4) 0.063(17) 0.03(2) 0.05(3) -0.09(5) C4Y 0.16(3) 0.24(3) 0.20(3) -0.01(2) 0.14(2) 0.01(2) C3Y 0.23(5) 0.40(6) 0.23(4) -0.14(4) 0.09(4) -0.06(4) C2Y 0.12(2) 0.14(2) 0.39(5) -0.07(3) 0.13(3) 0.008(17) C1Y 0.064(18) 0.20(3) 0.23(3) -0.12(2) 0.041(19) -0.031(17) N11X 0.100(15) 0.109(11) 0.073(10) -0.035(8) 0.033(10) 0.001(10) C10X 0.088(17) 0.065(12) 0.064(11) -0.030(10) 0.030(12) 0.030(13) N10X 0.088(13) 0.075(9) 0.077(10) -0.012(7) 0.034(10) -0.004(9) N9X 0.069(11) 0.077(10) 0.085(11) -0.026(9) 0.031(9) 0.007(10) C8X 0.055(13) 0.075(13) 0.053(13) -0.018(12) 0.023(12) 0.009(11) N8X 0.057(10) 0.080(9) 0.067(10) -0.018(8) 0.021(9) 0.007(8) N7X 0.073(11) 0.071(9) 0.069(11) -0.011(9) 0.027(10) 0.003(7) C6X 0.056(12) 0.082(14) 0.046(13) -0.007(13) 0.014(10) -0.008(10) C1X 0.047(11) 0.062(13) 0.062(13) -0.015(10) 0.012(10) -0.011(9) C2X 0.052(13) 0.094(15) 0.095(17) -0.005(13) 0.044(13) 0.021(10) C3X 0.072(13) 0.059(11) 0.064(12) -0.008(11) 0.039(10) 0.012(10) C4X 0.065(12) 0.070(14) 0.046(12) -0.023(10) 0.023(11) -0.003(10) C5X 0.058(12) 0.068(12) 0.070(14) -0.023(11) 0.026(11) 0.004(9) Cl3X 0.072(3) 0.103(3) 0.067(3) -0.006(2) 0.030(3) 0.000(2) K2 0.059(2) 0.0588(19) 0.0461(18) -0.0017(15) 0.0298(18) -0.0007(17) K1 0.106(3) 0.099(3) 0.068(2) 0.003(2) 0.040(2) -0.013(2) P3 0.091(4) 0.061(3) 0.052(3) 0.002(2) 0.042(3) 0.010(3) O11 0.086(8) 0.059(6) 0.048(6) -0.004(5) 0.044(6) 0.003(5) O12 0.074(8) 0.057(6) 0.056(6) 0.000(5) 0.020(6) -0.017(6) O13 0.083(8) 0.062(6) 0.048(6) 0.011(5) 0.031(6) 0.026(6) O14 0.064(7) 0.064(6) 0.047(6) -0.003(5) 0.027(5) 0.004(5) P4 0.077(4) 0.067(3) 0.051(3) -0.007(2) 0.029(3) -0.006(3) O7 0.086(8) 0.078(6) 0.043(6) 0.000(5) 0.029(6) -0.011(5) O8 0.096(9) 0.054(6) 0.066(7) -0.014(5) 0.037(7) -0.017(6) O9 0.072(8) 0.088(7) 0.056(6) -0.023(5) 0.038(6) -0.030(6) O10 0.077(8) 0.069(6) 0.036(5) 0.001(5) 0.030(5) -0.007(5) P1 0.062(3) 0.059(3) 0.042(2) 0.001(2) 0.025(3) 0.007(3) O17 0.042(6) 0.056(5) 0.044(5) 0.002(4) 0.028(5) 0.004(4) O18 0.062(7) 0.051(6) 0.058(6) -0.008(5) 0.024(6) -0.014(5) O19 0.072(8) 0.073(6) 0.060(6) -0.015(5) 0.036(7) -0.001(6) O20 0.069(7) 0.070(6) 0.047(6) -0.005(5) 0.028(5) 0.000(5) P2 0.094(4) 0.067(3) 0.057(3) 0.003(3) 0.036(3) -0.003(3) O21 0.088(10) 0.079(7) 0.102(9) 0.021(6) 0.035(8) -0.011(7) O22 0.074(7) 0.061(6) 0.040(5) -0.001(5) 0.031(6) -0.011(5) O23 0.055(7) 0.060(6) 0.070(6) 0.009(5) 0.030(6) -0.004(6) O24 0.122(10) 0.070(6) 0.060(7) 0.010(6) 0.040(7) 0.000(6) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 Cl3R C3R 1.765(16) . ? C5R C4R 1.349(19) . ? C5R C6R 1.43(2) . ? C5R H5R 0.95 . ? C4R C3R 1.37(2) . ? C4R H4R 0.95 . ? C3R C2R 1.38(2) . ? C2R C1R 1.40(2) . ? C2R H2R 0.95 . ? C1R C6R 1.40(2) . ? C1R H1R 0.95 . ? C6R N7R 1.39(2) . ? N7R C8R 1.376(18) . ? N7R H7R1 0.92 . ? C8R N8R 1.32(2) . ? C8R N9R 1.342(19) . ? N8R H8R1 0.88 . ? N8R H8R2 0.88 . ? N9R C10R 1.38(2) . ? C10R N10R 1.33(2) . ? C10R N11R 1.343(18) . ? N10R H10A 0.88 . ? N10R H10B 0.88 . ? N11R C6Y 1.51(2) . ? N11R H11A 0.92 . ? C6Y C5Y 1.531(19) . ? C6Y H6Y1 0.99 . ? C6Y H6Y2 0.99 . ? C5Y C4Y 1.473(18) . ? C5Y H5Y1 0.99 . ? C5Y H5Y2 0.99 . ? C4Y C3Y 1.546(18) . ? C4Y H4Y1 0.99 . ? C4Y H4Y2 0.99 . ? C3Y C2Y 1.505(19) . ? C3Y H3Y1 0.99 . ? C3Y H3Y2 0.99 . ? C2Y C1Y 1.531(17) . ? C2Y H2Y1 0.99 . ? C2Y H2Y2 0.99 . ? C1Y N11X 1.40(2) . ? C1Y H1Y1 0.99 . ? C1Y H1Y2 0.99 . ? N11X C10X 1.278(18) . ? N11X H11D 0.92 . ? C10X N10X 1.332(19) . ? C10X N9X 1.40(2) . ? N10X H10C 0.88 . ? N10X H10D 0.88 . ? N9X C8X 1.297(18) . ? C8X N7X 1.309(18) . ? C8X N8X 1.329(17) . ? N8X H8X1 0.88 . ? N8X H8X2 0.88 . ? N7X C6X 1.448(19) . ? N7X H7X1 0.92 . ? C6X C5X 1.370(19) . ? C6X C1X 1.371(19) . ? C1X C2X 1.45(2) . ? C1X H1X 0.95 . ? C2X C3X 1.32(2) . ? C2X H2X 0.95 . ? C3X C4X 1.367(18) . ? C3X Cl3X 1.742(16) . ? C4X C5X 1.327(19) . ? C4X H4X 0.95 . ? C5X H5X 0.95 . ? K2 O11 2.335(8) . ? K2 O2K 2.382(11) . ? K2 O18 2.407(9) . ? K2 O5K 2.421(8) . ? K2 O1K 2.433(8) . ? K2 O1A 2.435(12) . ? K2 O20 2.616(10) . ? K2 P1 3.051(5) . ? K2 P3 3.664(4) . ? K2 K1 4.464(5) . ? K1 O3K 2.237(13) . ? K1 O3A 2.255(12) . ? K1 O20 2.265(9) . ? K1 O2A 2.280(10) . ? K1 O4K 2.281(10) . ? K1 O7 2.286(10) . ? K1 C3A 3.30(2) . ? K1 C2A 3.43(2) . ? K1 P1 3.428(5) . ? K1 P4 3.558(6) . ? P3 O11 1.488(9) . ? P3 O12 1.515(10) . ? P3 O13 1.549(10) . ? P3 O14 1.656(8) . ? O14 C74 1.406(13) . ? P4 O9 1.501(10) . ? P4 O7 1.528(9) . ? P4 O8 1.536(10) . ? P4 O10 1.627(9) . ? O10 C93 1.415(14) . ? O15 C88 1.439(14) . ? O15 H15 0.84 . ? O16 C81 1.374(15) . ? O16 H16 0.84 . ? C73 C74 1.371(17) . ? C73 C78 1.431(16) . ? C73 C79 1.540(17) . ? C74 C75 1.420(17) . ? C75 C76 1.358(17) . ? C75 C86 1.469(19) . ? C76 C77 1.364(18) . ? C76 H76 0.95 . ? C77 C78 1.382(17) . ? C77 H77 0.95 . ? C78 H78 0.95 . ? C79 C82 1.492(17) . ? C79 H79A 0.99 . ? C79 H79B 0.99 . ? C80 C83 1.372(16) . ? C80 C82 1.399(18) . ? C80 H80 0.95 . ? C81 C85 1.395(15) . ? C81 C82 1.412(17) . ? C83 C84 1.392(17) . ? C83 H83 0.95 . ? C84 C85 1.399(17) . ? C84 H84 0.95 . ? C85 C100 1.498(17) . ? C86 C87 1.488(17) . ? C86 H86A 0.99 . ? C86 H86B 0.99 . ? C87 C88 1.327(15) . ? C87 C92 1.405(17) . ? C88 C89 1.388(16) . ? C89 C90 1.432(16) . ? C89 C99 1.486(16) . ? C90 C91 1.357(17) . ? C90 H90 0.95 . ? C91 C92 1.405(19) . ? C91 H91 0.95 . ? C92 H92 0.95 . ? C93 C94 1.360(17) . ? C93 C98 1.405(17) . ? C94 C95 1.441(17) . ? C94 C100 1.524(18) . ? C95 C96 1.364(18) . ? C95 H95 0.95 . ? C96 C97 1.354(19) . ? C96 H96 0.95 . ? C97 C98 1.432(18) . ? C97 H97 0.95 . ? C98 C99 1.510(18) . ? C99 H99A 0.99 . ? C99 H99B 0.99 . ? C100 H10E 0.99 . ? C100 H10F 0.99 . ? P1 O20 1.504(9) . ? P1 O19 1.505(11) . ? P1 O18 1.510(9) . ? P1 O17 1.630(8) . ? O17 C46 1.407(14) . ? P2 O24 1.470(10) . ? P2 O21 1.509(12) . ? P2 O23 1.527(10) . ? P2 O22 1.636(9) . ? O22 C33 1.377(14) . ? O25 C35 1.405(14) . ? O25 H25 0.84 . ? O26 C48 1.388(16) . ? O26 H26 0.84 . ? C51 C52 1.308(16) . ? C51 C47 1.440(18) . ? C51 H51 0.95 . ? C52 C53 1.398(18) . ? C52 H52 0.95 . ? C53 C49 1.355(18) . ? C53 H53 0.95 . ? C54 C47 1.516(16) . ? C54 C45 1.517(16) . ? C54 H54A 0.99 . ? C54 H54B 0.99 . ? C27 C28 1.487(18) . ? C27 C34 1.549(17) . ? C27 H27A 0.99 . ? C27 H27B 0.99 . ? C28 C29 1.425(17) . ? C28 C33 1.433(17) . ? C29 C30 1.343(19) . ? C29 H29 0.95 . ? C30 C31 1.391(17) . ? C30 H30 0.95 . ? C31 C32 1.382(16) . ? C31 H31 0.95 . ? C32 C33 1.396(18) . ? C32 C50 1.508(19) . ? C34 C35 1.376(17) . ? C34 C39 1.424(18) . ? C35 C36 1.378(16) . ? C36 C37 1.397(16) . ? C36 C43 1.533(17) . ? C37 C38 1.324(16) . ? C37 H37 0.95 . ? C38 C39 1.344(16) . ? C38 H38 0.95 . ? C39 H39 0.95 . ? C40 C41 1.349(18) . ? C40 C42 1.388(16) . ? C40 H40 0.95 . ? C41 C44 1.356(17) . ? C41 H41 0.95 . ? C42 C46 1.432(17) . ? C42 C43 1.567(19) . ? C43 H43A 0.99 . ? C43 H43B 0.99 . ? C44 C45 1.422(16) . ? C44 H44 0.95 . ? C45 C46 1.345(16) . ? C47 C48 1.380(17) . ? C48 C49 1.413(17) . ? C49 C50 1.519(18) . ? C50 H50A 0.99 . ? C50 H50B 0.99 . ? O1A C1A 1.487(19) . ? C1A H1A1 0.98 . ? C1A H1A2 0.98 . ? C1A H1A3 0.98 . ? O2A C2A 1.47(2) . ? C2A H2A1 0.98 . ? C2A H2A2 0.98 . ? C2A H2A3 0.98 . ? O3A C3A 1.477(19) . ? C3A H3A1 0.98 . ? C3A H3A2 0.98 . ? C3A H3A3 0.98 . ? O1M C1M 1.451(15) . ? O1M H1M 0.84 . ? C1M H1M1 0.98 . ? C1M H1M2 0.98 . ? C1M H1M3 0.98 . ? O2M C2M 1.426(17) . ? O2M H2M 0.84 . ? C2M H2M1 0.98 . ? C2M H2M2 0.98 . ? C2M H2M3 0.98 . ? O3M C3M 1.399(13) . ? O3M H3M 0.84 . ? C3M H3M1 0.98 . ? C3M H3M2 0.98 . ? C3M H3M3 0.98 . ? 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 C4R C5R C6R 122.2(16) . . ? C4R C5R H5R 118.9 . . ? C6R C5R H5R 118.9 . . ? C5R C4R C3R 119.5(15) . . ? C5R C4R H4R 120.3 . . ? C3R C4R H4R 120.3 . . ? C4R C3R C2R 121.8(15) . . ? C4R C3R Cl3R 120.8(16) . . ? C2R C3R Cl3R 117.4(16) . . ? C3R C2R C1R 118.9(15) . . ? C3R C2R H2R 120.5 . . ? C1R C2R H2R 120.5 . . ? C2R C1R C6R 120.9(15) . . ? C2R C1R H1R 119.6 . . ? C6R C1R H1R 119.6 . . ? N7R C6R C1R 115.5(15) . . ? N7R C6R C5R 127.2(17) . . ? C1R C6R C5R 116.5(17) . . ? C8R N7R C6R 129.7(15) . . ? C8R N7R H7R1 104.9 . . ? C6R N7R H7R1 104.9 . . ? N8R C8R N9R 125.1(14) . . ? N8R C8R N7R 117.7(16) . . ? N9R C8R N7R 117.2(18) . . ? C8R N8R H8R1 120 . . ? C8R N8R H8R2 120 . . ? H8R1 N8R H8R2 120 . . ? C8R N9R C10R 119.5(15) . . ? N10R C10R N11R 118.4(17) . . ? N10R C10R N9R 124.7(14) . . ? N11R C10R N9R 116.4(19) . . ? C10R N10R H10A 120 . . ? C10R N10R H10B 120 . . ? H10A N10R H10B 120 . . ? C10R N11R C6Y 124.4(14) . . ? C10R N11R H11A 106.2 . . ? C6Y N11R H11A 106.2 . . ? N11R C6Y C5Y 118.8(18) . . ? N11R C6Y H6Y1 107.6 . . ? C5Y C6Y H6Y1 107.6 . . ? N11R C6Y H6Y2 107.6 . . ? C5Y C6Y H6Y2 107.6 . . ? H6Y1 C6Y H6Y2 107 . . ? C4Y C5Y C6Y 109(2) . . ? C4Y C5Y H5Y1 109.9 . . ? C6Y C5Y H5Y1 109.9 . . ? C4Y C5Y H5Y2 109.9 . . ? C6Y C5Y H5Y2 109.9 . . ? H5Y1 C5Y H5Y2 108.3 . . ? C5Y C4Y C3Y 121(2) . . ? C5Y C4Y H4Y1 107.1 . . ? C3Y C4Y H4Y1 107.1 . . ? C5Y C4Y H4Y2 107.1 . . ? C3Y C4Y H4Y2 107.1 . . ? H4Y1 C4Y H4Y2 106.8 . . ? C2Y C3Y C4Y 115(2) . . ? C2Y C3Y H3Y1 108.5 . . ? C4Y C3Y H3Y1 108.5 . . ? C2Y C3Y H3Y2 108.5 . . ? C4Y C3Y H3Y2 108.5 . . ? H3Y1 C3Y H3Y2 107.5 . . ? C3Y C2Y C1Y 120(2) . . ? C3Y C2Y H2Y1 107.2 . . ? C1Y C2Y H2Y1 107.2 . . ? C3Y C2Y H2Y2 107.2 . . ? C1Y C2Y H2Y2 107.2 . . ? H2Y1 C2Y H2Y2 106.9 . . ? N11X C1Y C2Y 114.4(17) . . ? N11X C1Y H1Y1 108.7 . . ? C2Y C1Y H1Y1 108.7 . . ? N11X C1Y H1Y2 108.7 . . ? C2Y C1Y H1Y2 108.7 . . ? H1Y1 C1Y H1Y2 107.6 . . ? C10X N11X C1Y 127.5(17) . . ? C10X N11X H11D 105.4 . . ? C1Y N11X H11D 105.4 . . ? N11X C10X N10X 119.0(18) . . ? N11X C10X N9X 118(2) . . ? N10X C10X N9X 122.9(14) . . ? C10X N10X H10C 120 . . ? C10X N10X H10D 120 . . ? H10C N10X H10D 120 . . ? C8X N9X C10X 121.0(15) . . ? N9X C8X N7X 123.1(18) . . ? N9X C8X N8X 122.9(15) . . ? N7X C8X N8X 114.0(17) . . ? C8X N8X H8X1 120 . . ? C8X N8X H8X2 120 . . ? H8X1 N8X H8X2 120 . . ? C8X N7X C6X 129.5(15) . . ? C8X N7X H7X1 104.9 . . ? C6X N7X H7X1 104.9 . . ? C5X C6X C1X 118.4(15) . . ? C5X C6X N7X 119.1(18) . . ? C1X C6X N7X 122.1(16) . . ? C6X C1X C2X 119.5(14) . . ? C6X C1X H1X 120.2 . . ? C2X C1X H1X 120.2 . . ? C3X C2X C1X 117.2(15) . . ? C3X C2X H2X 121.4 . . ? C1X C2X H2X 121.4 . . ? C2X C3X C4X 123.3(16) . . ? C2X C3X Cl3X 118.3(15) . . ? C4X C3X Cl3X 118.4(15) . . ? C5X C4X C3X 119.1(14) . . ? C5X C4X H4X 120.4 . . ? C3X C4X H4X 120.4 . . ? C4X C5X C6X 122.3(16) . . ? C4X C5X H5X 118.9 . . ? C6X C5X H5X 118.9 . . ? O11 K2 O2K 110.2(4) . . ? O11 K2 O18 91.9(3) . . ? O2K K2 O18 77.6(4) . . ? O11 K2 O5K 82.6(3) . . ? O2K K2 O5K 147.5(4) . . ? O18 K2 O5K 133.3(3) . . ? O11 K2 O1K 157.1(3) . . ? O2K K2 O1K 92.7(3) . . ? O18 K2 O1K 93.4(3) . . ? O5K K2 O1K 77.6(3) . . ? O11 K2 O1A 97.8(3) . . ? O2K K2 O1A 73.1(4) . . ? O18 K2 O1A 150.6(3) . . ? O5K K2 O1A 75.7(3) . . ? O1K K2 O1A 88.3(3) . . ? O11 K2 O20 90.2(3) . . ? O2K K2 O20 132.1(3) . . ? O18 K2 O20 58.2(3) . . ? O5K K2 O20 75.4(3) . . ? O1K K2 O20 73.9(3) . . ? O1A K2 O20 148.6(3) . . ? O11 K2 P1 95.3(3) . . ? O2K K2 P1 103.5(3) . . ? O18 K2 P1 29.2(2) . . ? O5K K2 P1 104.9(2) . . ? O1K K2 P1 79.1(2) . . ? O1A K2 P1 166.8(3) . . ? O20 K2 P1 29.53(19) . . ? O11 K2 P3 13.2(3) . . ? O2K K2 P3 102.9(3) . . ? O18 K2 P3 101.2(2) . . ? O5K K2 P3 83.0(2) . . ? O1K K2 P3 160.5(2) . . ? O1A K2 P3 85.2(3) . . ? O20 K2 P3 103.0(2) . . ? P1 K2 P3 107.98(14) . . ? O11 K2 K1 76.8(3) . . ? O2K K2 K1 153.6(3) . . ? O18 K2 K1 76.8(2) . . ? O5K K2 K1 56.8(2) . . ? O1K K2 K1 82.8(2) . . ? O1A K2 K1 132.4(3) . . ? O20 K2 K1 22.08(18) . . ? P1 K2 K1 50.07(9) . . ? P3 K2 K1 88.15(11) . . ? O3K K1 O3A 96.9(5) . . ? O3K K1 O20 171.8(4) . . ? O3A K1 O20 89.4(4) . . ? O3K K1 O2A 92.5(5) . . ? O3A K1 O2A 93.0(4) . . ? O20 K1 O2A 81.9(3) . . ? O3K K1 O4K 104.9(4) . . ? O3A K1 O4K 87.3(4) . . ? O20 K1 O4K 80.6(3) . . ? O2A K1 O4K 162.5(4) . . ? O3K K1 O7 82.8(4) . . ? O3A K1 O7 178.0(4) . . ? O20 K1 O7 91.2(4) . . ? O2A K1 O7 89.0(4) . . ? O4K K1 O7 90.9(4) . . ? O3K K1 C3A 91.7(5) . . ? O3A K1 C3A 22.1(4) . . ? O20 K1 C3A 96.1(4) . . ? O2A K1 C3A 114.8(4) . . ? O4K K1 C3A 67.8(4) . . ? O7 K1 C3A 155.8(4) . . ? O3K K1 C2A 73.8(5) . . ? O3A K1 C2A 91.8(5) . . ? O20 K1 C2A 100.8(4) . . ? O2A K1 C2A 19.0(4) . . ? O4K K1 C2A 178.3(5) . . ? O7 K1 C2A 90.0(5) . . ? C3A K1 C2A 111.0(6) . . ? O3K K1 P1 163.4(4) . . ? O3A K1 P1 70.5(3) . . ? O20 K1 P1 19.7(2) . . ? O2A K1 P1 77.8(3) . . ? O4K K1 P1 85.8(3) . . ? O7 K1 P1 110.2(3) . . ? C3A K1 P1 80.5(3) . . ? C2A K1 P1 95.3(4) . . ? O3K K1 P4 66.1(4) . . ? O3A K1 P4 162.1(3) . . ? O20 K1 P4 108.1(3) . . ? O2A K1 P4 93.7(3) . . ? O4K K1 P4 91.3(3) . . ? O7 K1 P4 17.1(2) . . ? C3A K1 P4 145.2(3) . . ? C2A K1 P4 89.1(4) . . ? P1 K1 P4 127.26(17) . . ? O3K K1 K2 153.6(4) . . ? O3A K1 K2 104.4(3) . . ? O20 K1 K2 25.7(2) . . ? O2A K1 K2 101.7(3) . . ? O4K K1 K2 61.4(3) . . ? O7 K1 K2 75.4(3) . . ? C3A K1 K2 102.2(4) . . ? C2A K1 K2 120.2(4) . . ? P1 K1 K2 43.03(9) . . ? P4 K1 K2 90.54(12) . . ? O11 P3 O12 119.4(5) . . ? O11 P3 O13 106.7(6) . . ? O12 P3 O13 110.8(5) . . ? O11 P3 O14 102.5(4) . . ? O12 P3 O14 110.5(5) . . ? O13 P3 O14 105.9(5) . . ? O11 P3 K2 20.9(4) . . ? O12 P3 K2 101.0(4) . . ? O13 P3 K2 125.7(4) . . ? O14 P3 K2 102.4(3) . . ? P3 O11 K2 145.9(6) . . ? C74 O14 P3 123.7(7) . . ? O9 P4 O7 114.4(6) . . ? O9 P4 O8 113.4(6) . . ? O7 P4 O8 111.5(5) . . ? O9 P4 O10 109.8(5) . . ? O7 P4 O10 98.8(5) . . ? O8 P4 O10 107.9(5) . . ? O9 P4 K1 90.6(4) . . ? O7 P4 K1 26.1(4) . . ? O8 P4 K1 134.6(4) . . ? O10 P4 K1 98.3(3) . . ? P4 O7 K1 136.9(6) . . ? C93 O10 P4 123.7(7) . . ? C88 O15 H15 109.5 . . ? C81 O16 H16 109.5 . . ? C74 C73 C78 117.6(12) . . ? C74 C73 C79 124.6(11) . . ? C78 C73 C79 117.3(12) . . ? C73 C74 O14 118.7(11) . . ? C73 C74 C75 122.8(12) . . ? O14 C74 C75 118.3(12) . . ? C76 C75 C74 116.8(14) . . ? C76 C75 C86 121.4(12) . . ? C74 C75 C86 121.7(12) . . ? C75 C76 C77 122.6(13) . . ? C75 C76 H76 118.7 . . ? C77 C76 H76 118.7 . . ? C76 C77 C78 120.9(13) . . ? C76 C77 H77 119.6 . . ? C78 C77 H77 119.6 . . ? C77 C78 C73 119.1(14) . . ? C77 C78 H78 120.5 . . ? C73 C78 H78 120.5 . . ? C82 C79 C73 115.0(10) . . ? C82 C79 H79A 108.5 . . ? C73 C79 H79A 108.5 . . ? C82 C79 H79B 108.5 . . ? C73 C79 H79B 108.5 . . ? H79A C79 H79B 107.5 . . ? C83 C80 C82 119.7(13) . . ? C83 C80 H80 120.2 . . ? C82 C80 H80 120.2 . . ? O16 C81 C85 118.2(11) . . ? O16 C81 C82 117.3(11) . . ? C85 C81 C82 124.2(13) . . ? C80 C82 C81 116.9(12) . . ? C80 C82 C79 118.3(12) . . ? C81 C82 C79 124.8(13) . . ? C80 C83 C84 122.6(14) . . ? C80 C83 H83 118.7 . . ? C84 C83 H83 118.7 . . ? C83 C84 C85 120.0(13) . . ? C83 C84 H84 120 . . ? C85 C84 H84 120 . . ? C81 C85 C84 116.5(12) . . ? C81 C85 C100 122.0(12) . . ? C84 C85 C100 121.5(11) . . ? C75 C86 C87 113.2(11) . . ? C75 C86 H86A 108.9 . . ? C87 C86 H86A 108.9 . . ? C75 C86 H86B 108.9 . . ? C87 C86 H86B 108.9 . . ? H86A C86 H86B 107.8 . . ? C88 C87 C92 114.1(12) . . ? C88 C87 C86 126.7(12) . . ? C92 C87 C86 119.0(12) . . ? C87 C88 C89 130.4(12) . . ? C87 C88 O15 111.9(10) . . ? C89 C88 O15 117.6(10) . . ? C88 C89 C90 114.7(11) . . ? C88 C89 C99 127.6(12) . . ? C90 C89 C99 117.5(11) . . ? C91 C90 C89 116.7(13) . . ? C91 C90 H90 121.6 . . ? C89 C90 H90 121.6 . . ? C90 C91 C92 125.0(15) . . ? C90 C91 H91 117.5 . . ? C92 C91 H91 117.5 . . ? C91 C92 C87 118.8(14) . . ? C91 C92 H92 120.6 . . ? C87 C92 H92 120.6 . . ? C94 C93 C98 123.5(12) . . ? C94 C93 O10 119.7(12) . . ? C98 C93 O10 116.7(12) . . ? C93 C94 C95 119.8(13) . . ? C93 C94 C100 124.2(11) . . ? C95 C94 C100 115.7(13) . . ? C96 C95 C94 115.1(14) . . ? C96 C95 H95 122.4 . . ? C94 C95 H95 122.4 . . ? C97 C96 C95 126.6(14) . . ? C97 C96 H96 116.7 . . ? C95 C96 H96 116.7 . . ? C96 C97 C98 118.3(14) . . ? C96 C97 H97 120.9 . . ? C98 C97 H97 120.9 . . ? C93 C98 C97 116.3(13) . . ? C93 C98 C99 125.9(12) . . ? C97 C98 C99 117.2(12) . . ? C89 C99 C98 114.2(11) . . ? C89 C99 H99A 108.7 . . ? C98 C99 H99A 108.7 . . ? C89 C99 H99B 108.7 . . ? C98 C99 H99B 108.7 . . ? H99A C99 H99B 107.6 . . ? C85 C100 C94 112.6(10) . . ? C85 C100 H10E 109.1 . . ? C94 C100 H10E 109.1 . . ? C85 C100 H10F 109.1 . . ? C94 C100 H10F 109.1 . . ? H10E C100 H10F 107.8 . . ? O20 P1 O19 114.3(5) . . ? O20 P1 O18 108.7(5) . . ? O19 P1 O18 113.5(5) . . ? O20 P1 O17 104.7(5) . . ? O19 P1 O17 106.9(5) . . ? O18 P1 O17 108.2(5) . . ? O20 P1 K2 59.0(4) . . ? O19 P1 K2 144.1(4) . . ? O18 P1 K2 51.0(3) . . ? O17 P1 K2 108.9(4) . . ? O20 P1 K1 30.5(4) . . ? O19 P1 K1 84.6(4) . . ? O18 P1 K1 130.8(3) . . ? O17 P1 K1 109.1(3) . . ? K2 P1 K1 86.90(12) . . ? C46 O17 P1 120.5(7) . . ? P1 O18 K2 99.8(4) . . ? P1 O20 K1 129.8(6) . . ? P1 O20 K2 91.5(4) . . ? K1 O20 K2 132.2(4) . . ? O24 P2 O21 118.8(7) . . ? O24 P2 O23 108.3(6) . . ? O21 P2 O23 111.7(6) . . ? O24 P2 O22 103.0(5) . . ? O21 P2 O22 108.1(5) . . ? O23 P2 O22 105.9(6) . . ? C33 O22 P2 122.3(8) . . ? C35 O25 H25 109.5 . . ? C48 O26 H26 109.5 . . ? C52 C51 C47 119.9(14) . . ? C52 C51 H51 120.1 . . ? C47 C51 H51 120.1 . . ? C51 C52 C53 123.8(15) . . ? C51 C52 H52 118.1 . . ? C53 C52 H52 118.1 . . ? C49 C53 C52 118.1(13) . . ? C49 C53 H53 121 . . ? C52 C53 H53 121 . . ? C47 C54 C45 113.3(10) . . ? C47 C54 H54A 108.9 . . ? C45 C54 H54A 108.9 . . ? C47 C54 H54B 108.9 . . ? C45 C54 H54B 108.9 . . ? H54A C54 H54B 107.7 . . ? C28 C27 C34 111.2(11) . . ? C28 C27 H27A 109.4 . . ? C34 C27 H27A 109.4 . . ? C28 C27 H27B 109.4 . . ? C34 C27 H27B 109.4 . . ? H27A C27 H27B 108 . . ? C29 C28 C33 115.8(13) . . ? C29 C28 C27 119.8(12) . . ? C33 C28 C27 124.4(11) . . ? C30 C29 C28 121.7(14) . . ? C30 C29 H29 119.2 . . ? C28 C29 H29 119.2 . . ? C29 C30 C31 120.8(13) . . ? C29 C30 H30 119.6 . . ? C31 C30 H30 119.6 . . ? C32 C31 C30 121.6(14) . . ? C32 C31 H31 119.2 . . ? C30 C31 H31 119.2 . . ? C31 C32 C33 117.5(13) . . ? C31 C32 C50 121.5(14) . . ? C33 C32 C50 120.8(12) . . ? O22 C33 C32 122.3(12) . . ? O22 C33 C28 115.2(12) . . ? C32 C33 C28 122.4(12) . . ? C35 C34 C39 117.1(12) . . ? C35 C34 C27 121.9(12) . . ? C39 C34 C27 120.8(12) . . ? C34 C35 C36 122.2(12) . . ? C34 C35 O25 121.0(11) . . ? C36 C35 O25 116.3(11) . . ? C35 C36 C37 117.1(12) . . ? C35 C36 C43 121.4(11) . . ? C37 C36 C43 121.3(11) . . ? C38 C37 C36 121.8(12) . . ? C38 C37 H37 119.1 . . ? C36 C37 H37 119.1 . . ? C37 C38 C39 121.5(13) . . ? C37 C38 H38 119.2 . . ? C39 C38 H38 119.2 . . ? C38 C39 C34 120.0(13) . . ? C38 C39 H39 120 . . ? C34 C39 H39 120 . . ? C41 C40 C42 123.0(13) . . ? C41 C40 H40 118.5 . . ? C42 C40 H40 118.5 . . ? C40 C41 C44 119.7(13) . . ? C40 C41 H41 120.1 . . ? C44 C41 H41 120.1 . . ? C40 C42 C46 116.0(13) . . ? C40 C42 C43 121.9(12) . . ? C46 C42 C43 122.2(11) . . ? C36 C43 C42 112.1(11) . . ? C36 C43 H43A 109.2 . . ? C42 C43 H43A 109.2 . . ? C36 C43 H43B 109.2 . . ? C42 C43 H43B 109.2 . . ? H43A C43 H43B 107.9 . . ? C41 C44 C45 121.0(14) . . ? C41 C44 H44 119.5 . . ? C45 C44 H44 119.5 . . ? C46 C45 C44 118.1(12) . . ? C46 C45 C54 122.5(11) . . ? C44 C45 C54 119.3(12) . . ? C45 C46 O17 119.6(11) . . ? C45 C46 C42 122.0(12) . . ? O17 C46 C42 118.2(12) . . ? C48 C47 C51 117.1(12) . . ? C48 C47 C54 121.0(13) . . ? C51 C47 C54 121.8(12) . . ? C47 C48 O26 123.3(12) . . ? C47 C48 C49 121.0(14) . . ? O26 C48 C49 115.6(12) . . ? C53 C49 C48 120.1(13) . . ? C53 C49 C50 122.0(12) . . ? C48 C49 C50 117.8(13) . . ? C32 C50 C49 114.8(10) . . ? C32 C50 H50A 108.6 . . ? C49 C50 H50A 108.6 . . ? C32 C50 H50B 108.6 . . ? C49 C50 H50B 108.6 . . ? H50A C50 H50B 107.6 . . ? C1A O1A K2 144.8(10) . . ? O1A C1A H1A1 109.5 . . ? O1A C1A H1A2 109.5 . . ? H1A1 C1A H1A2 109.5 . . ? O1A C1A H1A3 109.5 . . ? H1A1 C1A H1A3 109.5 . . ? H1A2 C1A H1A3 109.5 . . ? C2A O2A K1 130.7(10) . . ? O2A C2A K1 30.3(7) . . ? O2A C2A H2A1 109.5 . . ? K1 C2A H2A1 100.4 . . ? O2A C2A H2A2 109.5 . . ? K1 C2A H2A2 86.5 . . ? H2A1 C2A H2A2 109.5 . . ? O2A C2A H2A3 109.5 . . ? K1 C2A H2A3 138 . . ? H2A1 C2A H2A3 109.5 . . ? H2A2 C2A H2A3 109.5 . . ? C3A O3A K1 122.7(10) . . ? O3A C3A K1 35.1(7) . . ? O3A C3A H3A1 109.5 . . ? K1 C3A H3A1 74.7 . . ? O3A C3A H3A2 109.5 . . ? K1 C3A H3A2 118.4 . . ? H3A1 C3A H3A2 109.5 . . ? O3A C3A H3A3 109.5 . . ? K1 C3A H3A3 127.3 . . ? H3A1 C3A H3A3 109.5 . . ? H3A2 C3A H3A3 109.5 . . ? C1M O1M H1M 109.5 . . ? O1M C1M H1M1 109.5 . . ? O1M C1M H1M2 109.5 . . ? H1M1 C1M H1M2 109.5 . . ? O1M C1M H1M3 109.5 . . ? H1M1 C1M H1M3 109.5 . . ? H1M2 C1M H1M3 109.5 . . ? C2M O2M H2M 109.5 . . ? O2M C2M H2M1 109.5 . . ? O2M C2M H2M2 109.5 . . ? H2M1 C2M H2M2 109.5 . . ? O2M C2M H2M3 109.5 . . ? H2M1 C2M H2M3 109.5 . . ? H2M2 C2M H2M3 109.5 . . ? C3M O3M H3M 109.5 . . ? O3M C3M H3M1 109.5 . . ? O3M C3M H3M2 109.5 . . ? H3M1 C3M H3M2 109.5 . . ? O3M C3M H3M3 109.5 . . ? H3M1 C3M H3M3 109.5 . . ? H3M2 C3M H3M3 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6X N7X C8X N9X 7(2) . . . . ? N7X C8X N9X C10X -150.1(15) . . . . ? C8X N9X C10X N11X -150.0(14) . . . . ? N9X C10X N11X C1Y 8(3) . . . . ? C10X N11X C1Y C2Y 162(2) . . . . ? N11X C1Y C2Y C3Y -178(3) . . . . ? C1Y C2Y C3Y C4Y -174(3) . . . . ? C2Y C3Y C4Y C5Y 21(5) . . . . ? C3Y C4Y C5Y C6Y 173(3) . . . . ? C4Y C5Y C6Y N11R -49(3) . . . . ? C5Y C6Y N11R C10R 106.1(19) . . . . ? C10R N9R C8R N7R -162.3(12) . . . . ? N9R C8R N7R C6R -3(2) . . . . ?