# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'L. Fabbrizzi' 'Valeria Amendola' 'Massimo Boiocchi' 'David Esteban-Gomez' 'Enrico Monzani' _publ_contact_author_name 'Prof L Fabbrizzi' _publ_contact_author_address ; Dipartimento Chimica Generale Universita di Pavia via Taramelli 12 Pavia I-27100 ; _publ_contact_author_email LUIGI.FABBRIZZI@UNIPV.IT _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; Chiral receptors for phosphate ions ; data_rr_h2po4 _database_code_depnum_ccdc_archive 'CCDC 268368' _audit_creation_method SHELXL-97 _chemical_name_systematic ; bis-tetrabutylammonium bis-dihydrogenphosphate 1-(4-nitrophenyl)-3-{2-[3-(4-nitrophenyl)ureido]-cyclohexyl}-urea acetonitrile ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H22 N6 O6, 2(C16 H36 N), 2(H2 O4 P), C2 H3 N' _chemical_formula_sum 'C54 H101 N9 O14 P2' _chemical_formula_weight 1162.38 _chemical_absolute_configuration ad loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 17.059(3) _cell_length_b 19.498(5) _cell_length_c 19.657(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 6538(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 7 _cell_measurement_theta_max 12 _exptl_crystal_description prism _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.68 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.45 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.181 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2520 _exptl_absorpt_coefficient_mu 0.131 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.919 _exptl_absorpt_correction_T_max 0.943 _exptl_absorpt_process_details ; North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351 Number of psi-scan sets used was 4 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Enraf-Nonius CAD4' _diffrn_measurement_method 'omega scans' _diffrn_standards_number 3 _diffrn_standards_interval_time 200 _diffrn_standards_decay_% 5 _diffrn_reflns_number 8008 _diffrn_reflns_av_R_equivalents 0.0456 _diffrn_reflns_av_sigmaI/netI 0.0837 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.47 _diffrn_reflns_theta_max 25.28 _reflns_number_total 7590 _reflns_number_gt 3662 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SIR-97 (Altomare et al.,1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1121P)^2^+1.9639P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.2(3) _refine_ls_number_reflns 7590 _refine_ls_number_parameters 713 _refine_ls_number_restraints 16 _refine_ls_R_factor_all 0.1662 _refine_ls_R_factor_gt 0.0771 _refine_ls_wR_factor_ref 0.2367 _refine_ls_wR_factor_gt 0.1864 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.3364(5) 0.0998(5) 0.8111(5) 0.072(3) Uani 1 1 d . . . H1 H 0.3175 0.0532 0.8021 0.087 Uiso 1 1 calc R . . C2 C 0.3801(6) 0.1270(6) 0.7488(6) 0.100(4) Uani 1 1 d . . . H2A H 0.4232 0.0962 0.7383 0.120 Uiso 1 1 calc R . . H2B H 0.4021 0.1716 0.7594 0.120 Uiso 1 1 calc R . . C3 C 0.3267(8) 0.1336(7) 0.6855(5) 0.117(4) Uani 1 1 d . . . H3A H 0.3557 0.1548 0.6487 0.140 Uiso 1 1 calc R . . H3B H 0.3104 0.0883 0.6707 0.140 Uiso 1 1 calc R . . C4 C 0.2565(8) 0.1755(7) 0.7016(6) 0.116(4) Uani 1 1 d . . . H4A H 0.2211 0.1745 0.6630 0.139 Uiso 1 1 calc R . . H4B H 0.2725 0.2227 0.7085 0.139 Uiso 1 1 calc R . . C5 C 0.2141(6) 0.1511(6) 0.7631(6) 0.100(4) Uani 1 1 d . . . H5A H 0.1922 0.1061 0.7540 0.120 Uiso 1 1 calc R . . H5B H 0.1708 0.1820 0.7725 0.120 Uiso 1 1 calc R . . C6 C 0.2668(5) 0.1470(5) 0.8259(5) 0.071(3) Uani 1 1 d . . . H6 H 0.2882 0.1930 0.8332 0.085 Uiso 1 1 calc R . . C7 C 0.4323(6) 0.0430(6) 0.8809(6) 0.071(3) Uani 1 1 d . . . C8 C 0.5246(6) 0.0005(5) 0.9690(6) 0.078(3) Uani 1 1 d . . . C9 C 0.5293(7) -0.0670(5) 0.9450(7) 0.106(4) Uani 1 1 d . . . H9 H 0.5054 -0.0785 0.9040 0.127 Uiso 1 1 calc R . . C10 C 0.5694(8) -0.1173(7) 0.9815(9) 0.119(5) Uani 1 1 d . . . H10 H 0.5718 -0.1624 0.9663 0.143 Uiso 1 1 calc R . . C11 C 0.6047(8) -0.0978(7) 1.0398(9) 0.107(4) Uani 1 1 d . . . C12 C 0.6024(7) -0.0325(8) 1.0663(7) 0.104(4) Uani 1 1 d . . . H12 H 0.6267 -0.0221 1.1074 0.125 Uiso 1 1 calc R . . C13 C 0.5635(6) 0.0165(6) 1.0303(6) 0.088(3) Uani 1 1 d . . . H13 H 0.5626 0.0613 1.0464 0.105 Uiso 1 1 calc R . . C14 C 0.1861(6) 0.0688(5) 0.8966(6) 0.075(3) Uani 1 1 d . . . C15 C 0.1046(5) 0.0102(6) 0.9841(6) 0.075(3) Uani 1 1 d . . . C16 C 0.0964(7) -0.0518(6) 0.9526(7) 0.108(4) Uani 1 1 d . . . H16 H 0.1163 -0.0585 0.9091 0.129 Uiso 1 1 calc R . . C17 C 0.0592(8) -0.1030(7) 0.9849(9) 0.120(4) Uani 1 1 d . . . H17 H 0.0552 -0.1452 0.9632 0.144 Uiso 1 1 calc R . . C18 C 0.0271(7) -0.0959(8) 1.0482(8) 0.100(4) Uani 1 1 d . . . C19 C 0.0310(8) -0.0324(8) 1.0773(6) 0.104(4) Uani 1 1 d . . . H19 H 0.0079 -0.0252 1.1195 0.125 Uiso 1 1 calc R . . C20 C 0.0681(6) 0.0204(6) 1.0459(6) 0.083(3) Uani 1 1 d . . . H20 H 0.0690 0.0635 1.0661 0.100 Uiso 1 1 calc R . . C21 C 0.2614(9) 0.4207(8) 0.1353(9) 0.145(5) Uani 1 1 d . . . H21A H 0.2148 0.4307 0.1088 0.174 Uiso 1 1 calc R . . H21B H 0.2727 0.3723 0.1297 0.174 Uiso 1 1 calc R . . C22 C 0.2430(10) 0.4325(11) 0.2060(11) 0.198(9) Uani 1 1 d . . . H22A H 0.2280 0.4802 0.2117 0.238 Uiso 1 1 calc R . . H22B H 0.2898 0.4248 0.2329 0.238 Uiso 1 1 calc R . . C23 C 0.1759(16) 0.3861(10) 0.2340(11) 0.227(10) Uani 1 1 d D . . H23A H 0.1797 0.3398 0.2163 0.273 Uiso 1 1 calc R . . H23B H 0.1763 0.3847 0.2833 0.273 Uiso 1 1 calc R . . C24 C 0.1077(11) 0.4206(17) 0.2087(11) 0.285(15) Uani 1 1 d D . . H24A H 0.0617 0.3956 0.2218 0.428 Uiso 1 1 calc R . . H24B H 0.1104 0.4232 0.1600 0.428 Uiso 1 1 calc R . . H24C H 0.1055 0.4660 0.2274 0.428 Uiso 1 1 calc R . . C25 C 0.3052(12) 0.5361(8) 0.1047(9) 0.195(9) Uani 1 1 d . . . H25A H 0.2521 0.5387 0.0873 0.234 Uiso 1 1 calc R . . H25B H 0.3031 0.5511 0.1517 0.234 Uiso 1 1 calc R . . C26 C 0.3480(18) 0.5842(13) 0.0700(15) 0.292(14) Uani 1 1 d . . . H26A H 0.3598 0.5643 0.0260 0.351 Uiso 1 1 calc R . . H26B H 0.3975 0.5883 0.0939 0.351 Uiso 1 1 calc R . . C27 C 0.3197(19) 0.6583(11) 0.0561(19) 0.33(2) Uani 1 1 d D . . H27A H 0.3630 0.6903 0.0609 0.395 Uiso 1 1 calc R . . H27B H 0.2993 0.6620 0.0102 0.395 Uiso 1 1 calc R . . C28 C 0.259(2) 0.6737(17) 0.1052(17) 0.41(3) Uani 1 1 d D . . H28A H 0.2335 0.7159 0.0931 0.618 Uiso 1 1 calc R . . H28B H 0.2816 0.6779 0.1497 0.618 Uiso 1 1 calc R . . H28C H 0.2209 0.6373 0.1055 0.618 Uiso 1 1 calc R . . C29 C 0.3448(13) 0.4370(9) 0.0341(12) 0.200(10) Uani 1 1 d D . . H29A H 0.3913 0.4626 0.0213 0.240 Uiso 1 1 calc R . . H29B H 0.3617 0.3898 0.0389 0.240 Uiso 1 1 calc R . . C30 C 0.2976(13) 0.4372(11) -0.0249(16) 0.230(12) Uani 1 1 d D . . H30A H 0.2751 0.4827 -0.0295 0.276 Uiso 1 1 calc R . . H30B H 0.2545 0.4057 -0.0173 0.276 Uiso 1 1 calc R . . C31 C 0.3337(15) 0.4194(11) -0.0898(12) 0.209(11) Uani 1 1 d D . . H31A H 0.3848 0.4408 -0.0938 0.250 Uiso 1 1 calc R . . H31B H 0.3401 0.3701 -0.0934 0.250 Uiso 1 1 calc R . . C32 C 0.2827(17) 0.444(2) -0.1415(15) 0.42(3) Uani 1 1 d D . . H32A H 0.3009 0.4282 -0.1850 0.636 Uiso 1 1 calc R . . H32B H 0.2819 0.4930 -0.1408 0.636 Uiso 1 1 calc R . . H32C H 0.2307 0.4266 -0.1336 0.636 Uiso 1 1 calc R . . C33 C 0.4006(12) 0.4574(13) 0.1524(12) 0.197(8) Uani 1 1 d D . . H33A H 0.4386 0.4898 0.1345 0.236 Uiso 1 1 calc R . . H33B H 0.3851 0.4740 0.1969 0.236 Uiso 1 1 calc R . . C34 C 0.439(2) 0.3946(12) 0.1617(16) 0.31(2) Uani 1 1 d D . . H34A H 0.4574 0.3769 0.1184 0.373 Uiso 1 1 calc R . . H34B H 0.4039 0.3613 0.1818 0.373 Uiso 1 1 calc R . . C35 C 0.5086(9) 0.4075(12) 0.2088(13) 0.197(10) Uani 1 1 d D . . H35A H 0.5358 0.3640 0.2116 0.236 Uiso 1 1 calc R . . H35B H 0.5430 0.4379 0.1837 0.236 Uiso 1 1 calc R . . C36 C 0.5080(16) 0.4339(14) 0.2773(12) 0.276(15) Uani 1 1 d D . . H36A H 0.5604 0.4333 0.2953 0.414 Uiso 1 1 calc R . . H36B H 0.4748 0.4058 0.3052 0.414 Uiso 1 1 calc R . . H36C H 0.4886 0.4801 0.2772 0.414 Uiso 1 1 calc R . . C37 C 0.2522(8) 0.9145(5) 0.7290(6) 0.102(4) Uani 1 1 d . . . H37A H 0.2969 0.9452 0.7271 0.122 Uiso 1 1 calc R . . H37B H 0.2116 0.9372 0.7553 0.122 Uiso 1 1 calc R . . C38 C 0.2218(8) 0.9037(6) 0.6568(6) 0.107(4) Uani 1 1 d . . . H38A H 0.2615 0.8800 0.6304 0.128 Uiso 1 1 calc R . . H38B H 0.1756 0.8747 0.6584 0.128 Uiso 1 1 calc R . . C39 C 0.2026(9) 0.9659(7) 0.6240(7) 0.130(5) Uani 1 1 d . . . H39A H 0.2500 0.9926 0.6177 0.156 Uiso 1 1 calc R . . H39B H 0.1677 0.9920 0.6531 0.156 Uiso 1 1 calc R . . C40 C 0.1646(9) 0.9558(8) 0.5573(8) 0.152(6) Uani 1 1 d . . . H40A H 0.1520 0.9996 0.5379 0.228 Uiso 1 1 calc R . . H40B H 0.1175 0.9295 0.5631 0.228 Uiso 1 1 calc R . . H40C H 0.1998 0.9317 0.5276 0.228 Uiso 1 1 calc R . . C41 C 0.3464(7) 0.8155(6) 0.7360(5) 0.092(3) Uani 1 1 d . . . H41A H 0.3579 0.7750 0.7629 0.110 Uiso 1 1 calc R . . H41B H 0.3331 0.8003 0.6904 0.110 Uiso 1 1 calc R . . C42 C 0.4183(9) 0.8583(8) 0.7321(9) 0.164(7) Uani 1 1 d . . . H42A H 0.4279 0.8803 0.7756 0.196 Uiso 1 1 calc R . . H42B H 0.4120 0.8937 0.6979 0.196 Uiso 1 1 calc R . . C43 C 0.4898(11) 0.8100(13) 0.7128(13) 0.239(11) Uani 1 1 d D . . H43A H 0.4804 0.7646 0.7314 0.287 Uiso 1 1 calc R . . H43B H 0.4925 0.8058 0.6637 0.287 Uiso 1 1 calc R . . C44 C 0.5649(17) 0.8350(13) 0.738(2) 0.39(3) Uani 1 1 d D . . H44A H 0.6060 0.8051 0.7228 0.588 Uiso 1 1 calc R . . H44B H 0.5641 0.8360 0.7868 0.588 Uiso 1 1 calc R . . H44C H 0.5740 0.8804 0.7208 0.588 Uiso 1 1 calc R . . C45 C 0.2931(7) 0.8723(6) 0.8407(5) 0.095(3) Uani 1 1 d . . . H45A H 0.3342 0.9068 0.8402 0.114 Uiso 1 1 calc R . . H45B H 0.2463 0.8940 0.8588 0.114 Uiso 1 1 calc R . . C46 C 0.3171(8) 0.8170(6) 0.8886(7) 0.118(4) Uani 1 1 d . . . H46A H 0.3617 0.7926 0.8698 0.141 Uiso 1 1 calc R . . H46B H 0.2743 0.7845 0.8935 0.141 Uiso 1 1 calc R . . C47 C 0.3395(12) 0.8461(12) 0.9608(10) 0.194(8) Uani 1 1 d D . . H47A H 0.3698 0.8120 0.9853 0.232 Uiso 1 1 calc R . . H47B H 0.3720 0.8865 0.9552 0.232 Uiso 1 1 calc R . . C48 C 0.2730(17) 0.8633(16) 0.9989(12) 0.338(19) Uani 1 1 d D . . H48A H 0.2888 0.8862 1.0399 0.508 Uiso 1 1 calc R . . H48B H 0.2447 0.8223 1.0103 0.508 Uiso 1 1 calc R . . H48C H 0.2400 0.8931 0.9727 0.508 Uiso 1 1 calc R . . C49 C 0.2116(6) 0.7977(5) 0.7658(5) 0.091(3) Uani 1 1 d . . . H49A H 0.2034 0.7831 0.7192 0.110 Uiso 1 1 calc R . . H49B H 0.2297 0.7580 0.7911 0.110 Uiso 1 1 calc R . . C50 C 0.1337(7) 0.8192(6) 0.7947(7) 0.110(4) Uani 1 1 d . . . H50A H 0.1379 0.8243 0.8436 0.132 Uiso 1 1 calc R . . H50B H 0.1185 0.8631 0.7756 0.132 Uiso 1 1 calc R . . C51 C 0.0734(9) 0.7669(8) 0.7782(9) 0.163(6) Uani 1 1 d . . . H51A H 0.0946 0.7218 0.7878 0.195 Uiso 1 1 calc R . . H51B H 0.0619 0.7691 0.7299 0.195 Uiso 1 1 calc R . . C52 C -0.0040(9) 0.7763(12) 0.8188(10) 0.229(10) Uani 1 1 d . . . H52A H -0.0409 0.7417 0.8053 0.344 Uiso 1 1 calc R . . H52B H -0.0255 0.8208 0.8095 0.344 Uiso 1 1 calc R . . H52C H 0.0066 0.7722 0.8666 0.344 Uiso 1 1 calc R . . N1 N 0.3895(4) 0.0993(4) 0.8694(4) 0.073(2) Uani 1 1 d . . . H1N H 0.3931 0.1344 0.8957 0.088 Uiso 1 1 calc R . . N2 N 0.4814(4) 0.0502(4) 0.9369(5) 0.075(2) Uani 1 1 d . . . H2N H 0.4850 0.0909 0.9536 0.090 Uiso 1 1 calc R . . N3 N 0.6512(8) -0.1492(9) 1.0811(9) 0.140(5) Uani 1 1 d . . . N4 N 0.2232(4) 0.1295(4) 0.8859(4) 0.079(2) Uani 1 1 d . . . H4N H 0.2203 0.1598 0.9176 0.095 Uiso 1 1 calc R . . N5 N 0.1441(4) 0.0663(4) 0.9568(4) 0.071(2) Uani 1 1 d . . . H5N H 0.1421 0.1037 0.9799 0.086 Uiso 1 1 calc R . . N6 N -0.0126(7) -0.1535(8) 1.0815(8) 0.128(4) Uani 1 1 d . . . N7 N 0.3274(7) 0.4601(5) 0.1058(6) 0.102(3) Uani 1 1 d . . . N8 N 0.2763(5) 0.8508(4) 0.7661(4) 0.083(2) Uani 1 1 d . . . O1 O 0.4283(4) -0.0084(3) 0.8482(4) 0.092(2) Uani 1 1 d . . . O2 O 0.6449(8) -0.2097(7) 1.0606(7) 0.190(6) Uani 1 1 d . . . O3 O 0.6836(8) -0.1306(7) 1.1320(7) 0.176(5) Uani 1 1 d . . . O4 O 0.1891(4) 0.0207(3) 0.8556(3) 0.089(2) Uani 1 1 d . . . O5 O -0.0055(8) -0.2090(6) 1.0579(7) 0.203(6) Uani 1 1 d . . . O6 O -0.0468(8) -0.1404(6) 1.1328(6) 0.170(5) Uani 1 1 d . . . P1 P 0.44285(13) 0.23870(13) 1.00366(16) 0.0722(7) Uani 1 1 d D . . O7 O 0.3812(3) 0.2337(3) 0.9465(3) 0.087(2) Uani 1 1 d . . . O8 O 0.4995(3) 0.1806(3) 0.9991(4) 0.0799(19) Uani 1 1 d . . . O9 O 0.4877(4) 0.3072(3) 0.9946(5) 0.106(3) Uani 1 1 d D . . H9O H 0.538(3) 0.305(3) 0.976(5) 0.128 Uiso 1 1 d D . . O10 O 0.3997(3) 0.2437(4) 1.0717(3) 0.094(2) Uani 1 1 d D . . H10O H 0.3448(14) 0.250(5) 1.067(3) 0.112 Uiso 1 1 d D . . P2 P 0.19417(12) 0.25032(13) 1.03108(12) 0.0618(6) Uani 1 1 d D . . O11 O 0.2360(3) 0.2541(4) 0.9624(3) 0.0734(16) Uani 1 1 d D . . H11O H 0.2886(19) 0.239(4) 0.966(3) 0.088 Uiso 1 1 d D . . O12 O 0.1387(3) 0.1904(3) 1.0335(3) 0.0718(17) Uani 1 1 d . . . O13 O 0.1455(3) 0.3183(3) 1.0369(4) 0.0795(19) Uani 1 1 d D . . H13O H 0.0914(15) 0.311(3) 1.044(5) 0.095 Uiso 1 1 d D . . O14 O 0.2533(3) 0.2522(3) 1.0882(3) 0.0690(15) Uani 1 1 d . . . C54 C 0.0993(17) 0.3065(11) -0.1423(10) 0.267(6) Uani 1 1 d . . . H54A H 0.1120 0.3239 -0.0980 0.401 Uiso 1 1 calc R . . H54B H 0.1333 0.2688 -0.1530 0.401 Uiso 1 1 calc R . . H54C H 0.0458 0.2912 -0.1429 0.401 Uiso 1 1 calc R . . C53 C 0.1086(19) 0.3553(12) -0.1877(12) 0.267(6) Uani 1 1 d . . . N9 N 0.1147(15) 0.4040(10) -0.2239(9) 0.267(6) 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 C1 0.075(6) 0.085(7) 0.057(7) -0.009(6) 0.001(6) -0.004(5) C2 0.087(7) 0.129(10) 0.084(9) -0.019(7) 0.015(7) -0.016(7) C3 0.125(10) 0.178(13) 0.048(8) -0.018(8) 0.005(8) 0.005(9) C4 0.121(10) 0.166(12) 0.061(8) 0.005(8) -0.002(8) 0.006(9) C5 0.098(8) 0.121(9) 0.079(9) -0.009(7) -0.032(8) 0.012(7) C6 0.076(6) 0.075(6) 0.061(7) -0.004(5) -0.012(6) -0.010(5) C7 0.076(6) 0.067(7) 0.071(8) -0.019(6) 0.001(6) -0.013(6) C8 0.077(6) 0.067(6) 0.091(9) 0.000(6) 0.015(7) 0.001(5) C9 0.116(9) 0.059(6) 0.143(12) -0.002(7) -0.029(9) 0.013(6) C10 0.137(11) 0.087(9) 0.134(13) -0.017(9) -0.030(10) 0.010(8) C11 0.117(10) 0.070(8) 0.135(13) 0.021(9) 0.011(9) 0.013(7) C12 0.104(9) 0.116(11) 0.092(10) 0.024(9) -0.028(7) -0.009(8) C13 0.086(7) 0.097(8) 0.079(9) -0.018(7) 0.003(7) -0.004(7) C14 0.083(7) 0.069(7) 0.074(8) -0.020(6) -0.007(7) 0.023(6) C15 0.068(6) 0.078(7) 0.078(9) -0.013(7) -0.014(6) 0.014(5) C16 0.119(9) 0.097(9) 0.107(10) -0.032(8) 0.045(8) -0.025(8) C17 0.133(11) 0.100(9) 0.126(13) -0.030(9) 0.007(10) -0.041(8) C18 0.080(7) 0.131(12) 0.088(11) 0.006(10) 0.010(8) -0.016(8) C19 0.133(10) 0.112(10) 0.068(8) 0.003(9) 0.009(8) 0.006(9) C20 0.102(8) 0.083(8) 0.064(8) -0.007(7) 0.003(7) 0.020(7) C21 0.141(12) 0.150(13) 0.144(15) -0.013(11) 0.021(11) -0.050(11) C22 0.157(15) 0.27(2) 0.172(19) 0.024(17) 0.070(14) -0.078(15) C23 0.30(3) 0.20(2) 0.19(2) 0.034(16) -0.03(2) 0.05(2) C24 0.160(18) 0.54(5) 0.154(18) 0.08(2) -0.042(15) 0.02(2) C25 0.27(2) 0.103(11) 0.212(18) -0.061(11) 0.137(17) -0.106(13) C26 0.35(4) 0.17(2) 0.36(4) 0.00(2) 0.10(3) -0.01(2) C27 0.38(4) 0.104(16) 0.50(6) 0.03(2) 0.14(4) 0.02(2) C28 0.55(8) 0.29(4) 0.39(5) -0.19(3) 0.03(5) 0.04(4) C29 0.25(2) 0.133(13) 0.22(2) -0.045(14) -0.10(2) 0.074(14) C30 0.159(18) 0.177(19) 0.35(4) 0.07(2) -0.02(3) 0.015(14) C31 0.28(3) 0.164(16) 0.18(2) 0.039(15) 0.10(2) 0.026(17) C32 0.39(5) 0.61(7) 0.27(4) 0.18(4) 0.15(3) 0.26(5) C33 0.162(17) 0.21(2) 0.22(2) 0.005(19) 0.048(17) -0.028(18) C34 0.40(5) 0.17(2) 0.36(4) -0.13(3) 0.20(4) -0.07(3) C35 0.088(10) 0.23(2) 0.27(3) 0.01(2) -0.036(15) -0.058(12) C36 0.24(3) 0.42(4) 0.17(2) -0.08(2) 0.06(2) 0.00(2) C37 0.146(10) 0.069(7) 0.091(9) 0.002(7) 0.005(8) 0.009(7) C38 0.161(12) 0.075(8) 0.085(9) -0.009(7) -0.001(8) 0.006(8) C39 0.148(12) 0.108(10) 0.133(12) 0.000(10) -0.038(11) 0.017(9) C40 0.147(13) 0.157(13) 0.152(14) 0.001(11) -0.038(12) -0.009(10) C41 0.115(9) 0.087(8) 0.074(8) -0.011(6) 0.018(7) 0.011(7) C42 0.150(13) 0.171(14) 0.170(16) -0.049(12) 0.070(12) -0.067(12) C43 0.130(14) 0.27(3) 0.32(3) -0.07(2) 0.106(19) -0.010(17) C44 0.32(4) 0.21(3) 0.65(8) -0.06(3) 0.14(5) -0.03(3) C45 0.108(8) 0.097(8) 0.079(8) -0.033(7) -0.003(7) -0.010(7) C46 0.134(10) 0.123(10) 0.095(10) 0.005(9) 0.000(9) 0.006(9) C47 0.195(19) 0.26(2) 0.123(17) -0.040(15) 0.029(14) -0.048(16) C48 0.43(5) 0.42(4) 0.16(2) -0.08(3) 0.05(3) -0.13(4) C49 0.113(9) 0.080(7) 0.081(8) -0.021(6) 0.002(7) 0.011(7) C50 0.102(8) 0.107(9) 0.121(10) -0.043(8) 0.012(8) -0.007(8) C51 0.128(11) 0.172(14) 0.188(16) -0.034(12) -0.006(11) -0.012(12) C52 0.104(10) 0.36(3) 0.225(19) -0.090(19) 0.041(12) -0.040(14) N1 0.079(5) 0.073(5) 0.067(6) -0.016(4) -0.010(5) 0.005(4) N2 0.071(5) 0.059(5) 0.094(7) -0.007(5) 0.001(5) 0.003(4) N3 0.138(11) 0.136(12) 0.147(13) 0.041(12) -0.017(9) 0.023(10) N4 0.087(5) 0.069(5) 0.081(6) -0.019(5) 0.003(5) -0.012(5) N5 0.082(5) 0.068(5) 0.064(6) -0.016(5) 0.016(5) 0.007(4) N6 0.132(10) 0.135(11) 0.116(11) -0.020(10) 0.020(8) -0.018(9) N7 0.105(8) 0.097(8) 0.103(9) -0.033(7) 0.034(7) -0.020(6) N8 0.105(6) 0.070(6) 0.073(6) -0.015(5) -0.002(5) -0.018(5) O1 0.116(5) 0.067(4) 0.091(5) -0.026(4) -0.018(4) 0.005(4) O2 0.234(13) 0.118(8) 0.219(13) 0.033(9) -0.060(10) 0.024(9) O3 0.180(10) 0.180(11) 0.166(11) 0.045(9) -0.053(10) 0.037(9) O4 0.100(5) 0.081(5) 0.087(5) -0.024(4) 0.019(5) -0.005(4) O5 0.262(14) 0.114(8) 0.233(14) -0.032(9) 0.087(12) -0.052(9) O6 0.217(12) 0.158(9) 0.134(9) -0.013(8) 0.059(9) -0.056(8) P1 0.0552(12) 0.0767(17) 0.0848(19) -0.0105(16) -0.0002(13) -0.0028(13) O7 0.065(3) 0.108(5) 0.089(5) -0.024(4) -0.011(3) 0.004(4) O8 0.063(3) 0.053(3) 0.124(6) -0.005(4) 0.012(4) 0.001(3) O9 0.075(4) 0.057(4) 0.187(8) -0.018(5) 0.011(5) -0.002(3) O10 0.059(3) 0.130(6) 0.092(5) -0.018(5) -0.003(4) 0.009(5) P2 0.0555(11) 0.0622(14) 0.0677(16) -0.0036(15) 0.0003(13) 0.0011(13) O11 0.068(3) 0.097(4) 0.056(4) 0.002(4) -0.001(3) 0.003(4) O12 0.066(3) 0.065(4) 0.084(5) -0.007(3) -0.007(3) 0.002(3) O13 0.063(4) 0.066(4) 0.109(6) -0.020(4) -0.002(4) 0.003(3) O14 0.067(3) 0.092(4) 0.048(3) -0.001(4) -0.002(3) 0.001(4) C54 0.446(17) 0.195(15) 0.160(13) 0.046(8) -0.086(14) 0.023(15) C53 0.446(17) 0.195(15) 0.160(13) 0.046(8) -0.086(14) 0.023(15) N9 0.446(17) 0.195(15) 0.160(13) 0.046(8) -0.086(14) 0.023(15) _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 C1 N1 1.461(11) . ? C1 C6 1.528(12) . ? C1 C2 1.528(13) . ? C1 H1 0.9800 . ? C2 C3 1.548(14) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.484(15) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.487(15) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.531(12) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 N4 1.437(11) . ? C6 H6 0.9800 . ? C7 O1 1.193(10) . ? C7 N1 1.337(12) . ? C7 N2 1.391(12) . ? C8 N2 1.371(12) . ? C8 C9 1.402(14) . ? C8 C13 1.410(14) . ? C9 C10 1.394(16) . ? C9 H9 0.9300 . ? C10 C11 1.348(17) . ? C10 H10 0.9300 . ? C11 C12 1.378(17) . ? C11 N3 1.514(18) . ? C12 C13 1.361(14) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 O4 1.238(10) . ? C14 N4 1.359(12) . ? C14 N5 1.383(12) . ? C15 C16 1.365(14) . ? C15 C20 1.380(13) . ? C15 N5 1.392(12) . ? C16 C17 1.341(16) . ? C16 H16 0.9300 . ? C17 C18 1.367(16) . ? C17 H17 0.9300 . ? C18 C19 1.365(16) . ? C18 N6 1.466(17) . ? C19 C20 1.356(15) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 C22 1.44(2) . ? C21 N7 1.482(16) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C23 1.56(2) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C24 1.432(16) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 C26 1.37(2) . ? C25 N7 1.529(18) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 C27 1.55(3) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C27 C28 1.451(19) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 C30 1.413(17) . ? C29 N7 1.51(2) . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C30 C31 1.46(3) . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C31 C32 1.419(18) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C33 C34 1.402(18) . ? C33 N7 1.55(2) . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C34 C35 1.52(3) . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C35 C36 1.442(16) . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 0.9600 . ? C37 N8 1.498(12) . ? C37 C38 1.526(15) . ? C37 H37A 0.9700 . ? C37 H37B 0.9700 . ? C38 C39 1.412(14) . ? C38 H38A 0.9700 . ? C38 H38B 0.9700 . ? C39 C40 1.474(17) . ? C39 H39A 0.9700 . ? C39 H39B 0.9700 . ? C40 H40A 0.9600 . ? C40 H40B 0.9600 . ? C40 H40C 0.9600 . ? C41 C42 1.486(15) . ? C41 N8 1.502(12) . ? C41 H41A 0.9700 . ? C41 H41B 0.9700 . ? C42 C43 1.59(2) . ? C42 H42A 0.9700 . ? C42 H42B 0.9700 . ? C43 C44 1.456(18) . ? C43 H43A 0.9700 . ? C43 H43B 0.9700 . ? C44 H44A 0.9600 . ? C44 H44B 0.9600 . ? C44 H44C 0.9600 . ? C45 C46 1.490(14) . ? C45 N8 1.553(12) . ? C45 H45A 0.9700 . ? C45 H45B 0.9700 . ? C46 C47 1.576(19) . ? C46 H46A 0.9700 . ? C46 H46B 0.9700 . ? C47 C48 1.399(17) . ? C47 H47A 0.9700 . ? C47 H47B 0.9700 . ? C48 H48A 0.9600 . ? C48 H48B 0.9600 . ? C48 H48C 0.9600 . ? C49 C50 1.504(13) . ? C49 N8 1.513(12) . ? C49 H49A 0.9700 . ? C49 H49B 0.9700 . ? C50 C51 1.484(15) . ? C50 H50A 0.9700 . ? C50 H50B 0.9700 . ? C51 C52 1.553(18) . ? C51 H51A 0.9700 . ? C51 H51B 0.9700 . ? C52 H52A 0.9600 . ? C52 H52B 0.9600 . ? C52 H52C 0.9600 . ? N1 H1N 0.8600 . ? N2 H2N 0.8600 . ? N3 O3 1.199(15) . ? N3 O2 1.252(15) . ? N4 H4N 0.8600 . ? N5 H5N 0.8600 . ? N6 O5 1.184(13) . ? N6 O6 1.193(13) . ? P1 O8 1.493(6) . ? P1 O10 1.530(7) . ? P1 O7 1.542(6) . ? P1 O9 1.549(6) . ? O9 H9O 0.94(2) . ? O10 H10O 0.95(2) . ? P2 O12 1.505(6) . ? P2 O14 1.510(5) . ? P2 O11 1.528(6) . ? P2 O13 1.568(6) . ? O11 H11O 0.95(2) . ? O13 H13O 0.94(2) . ? C54 C53 1.31(3) . ? C54 H54A 0.9600 . ? C54 H54B 0.9600 . ? C54 H54C 0.9600 . ? C53 N9 1.19(2) . ? 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 N1 C1 C6 109.7(8) . . ? N1 C1 C2 109.1(8) . . ? C6 C1 C2 108.9(9) . . ? N1 C1 H1 109.7 . . ? C6 C1 H1 109.7 . . ? C2 C1 H1 109.7 . . ? C1 C2 C3 112.6(9) . . ? C1 C2 H2A 109.1 . . ? C3 C2 H2A 109.1 . . ? C1 C2 H2B 109.1 . . ? C3 C2 H2B 109.1 . . ? H2A C2 H2B 107.8 . . ? C4 C3 C2 110.5(9) . . ? C4 C3 H3A 109.5 . . ? C2 C3 H3A 109.6 . . ? C4 C3 H3B 109.6 . . ? C2 C3 H3B 109.6 . . ? H3A C3 H3B 108.1 . . ? C3 C4 C5 112.9(11) . . ? C3 C4 H4A 109.0 . . ? C5 C4 H4A 109.0 . . ? C3 C4 H4B 109.0 . . ? C5 C4 H4B 109.0 . . ? H4A C4 H4B 107.8 . . ? C4 C5 C6 112.7(9) . . ? C4 C5 H5A 109.0 . . ? C6 C5 H5A 109.0 . . ? C4 C5 H5B 109.0 . . ? C6 C5 H5B 109.0 . . ? H5A C5 H5B 107.8 . . ? N4 C6 C1 114.6(8) . . ? N4 C6 C5 111.8(8) . . ? C1 C6 C5 109.5(8) . . ? N4 C6 H6 106.8 . . ? C1 C6 H6 106.8 . . ? C5 C6 H6 106.8 . . ? O1 C7 N1 124.6(10) . . ? O1 C7 N2 123.0(10) . . ? N1 C7 N2 112.4(9) . . ? N2 C8 C9 122.7(11) . . ? N2 C8 C13 119.4(10) . . ? C9 C8 C13 117.9(11) . . ? C10 C9 C8 121.0(12) . . ? C10 C9 H9 119.5 . . ? C8 C9 H9 119.5 . . ? C11 C10 C9 117.4(12) . . ? C11 C10 H10 121.3 . . ? C9 C10 H10 121.3 . . ? C10 C11 C12 124.7(13) . . ? C10 C11 N3 120.3(14) . . ? C12 C11 N3 115.1(16) . . ? C13 C12 C11 117.8(12) . . ? C13 C12 H12 121.1 . . ? C11 C12 H12 121.1 . . ? C12 C13 C8 121.3(11) . . ? C12 C13 H13 119.4 . . ? C8 C13 H13 119.4 . . ? O4 C14 N4 122.6(11) . . ? O4 C14 N5 123.5(10) . . ? N4 C14 N5 113.8(9) . . ? C16 C15 C20 118.7(11) . . ? C16 C15 N5 124.9(11) . . ? C20 C15 N5 116.4(10) . . ? C17 C16 C15 119.6(12) . . ? C17 C16 H16 120.2 . . ? C15 C16 H16 120.2 . . ? C16 C17 C18 123.0(12) . . ? C16 C17 H17 118.5 . . ? C18 C17 H17 118.5 . . ? C19 C18 C17 117.0(13) . . ? C19 C18 N6 122.0(14) . . ? C17 C18 N6 120.9(15) . . ? C20 C19 C18 121.3(12) . . ? C20 C19 H19 119.3 . . ? C18 C19 H19 119.3 . . ? C19 C20 C15 120.1(11) . . ? C19 C20 H20 119.9 . . ? C15 C20 H20 119.9 . . ? C22 C21 N7 117.3(13) . . ? C22 C21 H21A 108.0 . . ? N7 C21 H21A 108.0 . . ? C22 C21 H21B 108.0 . . ? N7 C21 H21B 108.0 . . ? H21A C21 H21B 107.2 . . ? C21 C22 C23 114.0(18) . . ? C21 C22 H22A 108.7 . . ? C23 C22 H22A 108.7 . . ? C21 C22 H22B 108.8 . . ? C23 C22 H22B 108.7 . . ? H22A C22 H22B 107.6 . . ? C24 C23 C22 101.6(17) . . ? C24 C23 H23A 111.5 . . ? C22 C23 H23A 111.4 . . ? C24 C23 H23B 111.4 . . ? C22 C23 H23B 111.5 . . ? H23A C23 H23B 109.3 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C26 C25 N7 122.6(17) . . ? C26 C25 H25A 106.7 . . ? N7 C25 H25A 106.7 . . ? C26 C25 H25B 106.7 . . ? N7 C25 H25B 106.7 . . ? H25A C25 H25B 106.6 . . ? C25 C26 C27 124(2) . . ? C25 C26 H26A 106.3 . . ? C27 C26 H26A 106.3 . . ? C25 C26 H26B 106.3 . . ? C27 C26 H26B 106.3 . . ? H26A C26 H26B 106.4 . . ? C28 C27 C26 107(3) . . ? C28 C27 H27A 110.3 . . ? C26 C27 H27A 110.3 . . ? C28 C27 H27B 110.3 . . ? C26 C27 H27B 110.3 . . ? H27A C27 H27B 108.5 . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C30 C29 N7 131(2) . . ? C30 C29 H29A 104.5 . . ? N7 C29 H29A 104.5 . . ? C30 C29 H29B 104.5 . . ? N7 C29 H29B 104.5 . . ? H29A C29 H29B 105.7 . . ? C29 C30 C31 119(2) . . ? C29 C30 H30A 107.7 . . ? C31 C30 H30A 107.7 . . ? C29 C30 H30B 107.7 . . ? C31 C30 H30B 107.7 . . ? H30A C30 H30B 107.1 . . ? C32 C31 C30 107(2) . . ? C32 C31 H31A 110.4 . . ? C30 C31 H31A 110.4 . . ? C32 C31 H31B 110.4 . . ? C30 C31 H31B 110.4 . . ? H31A C31 H31B 108.6 . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C34 C33 N7 119(3) . . ? C34 C33 H33A 107.6 . . ? N7 C33 H33A 107.6 . . ? C34 C33 H33B 107.6 . . ? N7 C33 H33B 107.6 . . ? H33A C33 H33B 107.0 . . ? C33 C34 C35 107(2) . . ? C33 C34 H34A 110.2 . . ? C35 C34 H34A 110.2 . . ? C33 C34 H34B 110.2 . . ? C35 C34 H34B 110.2 . . ? H34A C34 H34B 108.5 . . ? C36 C35 C34 128(2) . . ? C36 C35 H35A 105.2 . . ? C34 C35 H35A 105.2 . . ? C36 C35 H35B 105.2 . . ? C34 C35 H35B 105.2 . . ? H35A C35 H35B 105.9 . . ? C35 C36 H36A 109.5 . . ? C35 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C35 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? N8 C37 C38 115.6(9) . . ? N8 C37 H37A 108.4 . . ? C38 C37 H37A 108.4 . . ? N8 C37 H37B 108.4 . . ? C38 C37 H37B 108.4 . . ? H37A C37 H37B 107.4 . . ? C39 C38 C37 112.7(10) . . ? C39 C38 H38A 109.1 . . ? C37 C38 H38A 109.1 . . ? C39 C38 H38B 109.1 . . ? C37 C38 H38B 109.1 . . ? H38A C38 H38B 107.8 . . ? C38 C39 C40 113.2(12) . . ? C38 C39 H39A 108.9 . . ? C40 C39 H39A 108.9 . . ? C38 C39 H39B 108.9 . . ? C40 C39 H39B 108.9 . . ? H39A C39 H39B 107.8 . . ? C39 C40 H40A 109.5 . . ? C39 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? C39 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? C42 C41 N8 114.9(10) . . ? C42 C41 H41A 108.5 . . ? N8 C41 H41A 108.5 . . ? C42 C41 H41B 108.5 . . ? N8 C41 H41B 108.5 . . ? H41A C41 H41B 107.5 . . ? C41 C42 C43 108.3(13) . . ? C41 C42 H42A 110.0 . . ? C43 C42 H42A 110.0 . . ? C41 C42 H42B 110.0 . . ? C43 C42 H42B 110.0 . . ? H42A C42 H42B 108.4 . . ? C44 C43 C42 113(2) . . ? C44 C43 H43A 108.9 . . ? C42 C43 H43A 108.9 . . ? C44 C43 H43B 108.9 . . ? C42 C43 H43B 108.9 . . ? H43A C43 H43B 107.7 . . ? C43 C44 H44A 109.5 . . ? C43 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? C43 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? C46 C45 N8 116.8(9) . . ? C46 C45 H45A 108.1 . . ? N8 C45 H45A 108.1 . . ? C46 C45 H45B 108.1 . . ? N8 C45 H45B 108.1 . . ? H45A C45 H45B 107.3 . . ? C45 C46 C47 112.0(13) . . ? C45 C46 H46A 109.2 . . ? C47 C46 H46A 109.2 . . ? C45 C46 H46B 109.2 . . ? C47 C46 H46B 109.2 . . ? H46A C46 H46B 107.9 . . ? C48 C47 C46 111.8(17) . . ? C48 C47 H47A 109.3 . . ? C46 C47 H47A 109.2 . . ? C48 C47 H47B 109.2 . . ? C46 C47 H47B 109.2 . . ? H47A C47 H47B 107.9 . . ? C47 C48 H48A 109.5 . . ? C47 C48 H48B 109.5 . . ? H48A C48 H48B 109.5 . . ? C47 C48 H48C 109.5 . . ? H48A C48 H48C 109.5 . . ? H48B C48 H48C 109.5 . . ? C50 C49 N8 116.8(8) . . ? C50 C49 H49A 108.1 . . ? N8 C49 H49A 108.1 . . ? C50 C49 H49B 108.1 . . ? N8 C49 H49B 108.1 . . ? H49A C49 H49B 107.3 . . ? C51 C50 C49 109.8(10) . . ? C51 C50 H50A 109.7 . . ? C49 C50 H50A 109.7 . . ? C51 C50 H50B 109.7 . . ? C49 C50 H50B 109.7 . . ? H50A C50 H50B 108.2 . . ? C50 C51 C52 113.4(13) . . ? C50 C51 H51A 108.9 . . ? C52 C51 H51A 108.9 . . ? C50 C51 H51B 108.9 . . ? C52 C51 H51B 108.9 . . ? H51A C51 H51B 107.7 . . ? C51 C52 H52A 109.5 . . ? C51 C52 H52B 109.5 . . ? H52A C52 H52B 109.5 . . ? C51 C52 H52C 109.5 . . ? H52A C52 H52C 109.5 . . ? H52B C52 H52C 109.5 . . ? C7 N1 C1 118.5(9) . . ? C7 N1 H1N 120.7 . . ? C1 N1 H1N 120.7 . . ? C8 N2 C7 128.1(9) . . ? C8 N2 H2N 115.9 . . ? C7 N2 H2N 115.9 . . ? O3 N3 O2 126.4(16) . . ? O3 N3 C11 119.3(17) . . ? O2 N3 C11 113.9(16) . . ? C14 N4 C6 125.1(8) . . ? C14 N4 H4N 117.4 . . ? C6 N4 H4N 117.4 . . ? C14 N5 C15 127.4(9) . . ? C14 N5 H5N 116.3 . . ? C15 N5 H5N 116.3 . . ? O5 N6 O6 125.3(17) . . ? O5 N6 C18 118.6(15) . . ? O6 N6 C18 116.0(15) . . ? C21 N7 C29 111.1(13) . . ? C21 N7 C25 108.6(11) . . ? C29 N7 C25 108.9(12) . . ? C21 N7 C33 111.4(12) . . ? C29 N7 C33 112.6(14) . . ? C25 N7 C33 103.9(14) . . ? C37 N8 C41 114.0(8) . . ? C37 N8 C49 111.4(9) . . ? C41 N8 C49 105.4(8) . . ? C37 N8 C45 106.6(8) . . ? C41 N8 C45 110.4(8) . . ? C49 N8 C45 108.9(8) . . ? O8 P1 O10 114.3(4) . . ? O8 P1 O7 110.5(4) . . ? O10 P1 O7 108.2(3) . . ? O8 P1 O9 109.2(3) . . ? O10 P1 O9 106.5(5) . . ? O7 P1 O9 107.9(4) . . ? P1 O9 H9O 118(4) . . ? P1 O10 H10O 114(3) . . ? O12 P2 O14 114.6(4) . . ? O12 P2 O11 111.0(4) . . ? O14 P2 O11 110.1(3) . . ? O12 P2 O13 108.7(3) . . ? O14 P2 O13 106.2(4) . . ? O11 P2 O13 105.8(4) . . ? P2 O11 H11O 111(3) . . ? P2 O13 H13O 114(3) . . ? C53 C54 H54A 109.5 . . ? C53 C54 H54B 109.5 . . ? H54A C54 H54B 109.5 . . ? C53 C54 H54C 109.5 . . ? H54A C54 H54C 109.5 . . ? H54B C54 H54C 109.5 . . ? N9 C53 C54 173(3) . . ? 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 N1 C1 C2 C3 -176.5(9) . . . . ? C6 C1 C2 C3 -56.8(12) . . . . ? C1 C2 C3 C4 54.0(14) . . . . ? C2 C3 C4 C5 -52.1(14) . . . . ? C3 C4 C5 C6 55.4(14) . . . . ? N1 C1 C6 N4 -57.1(10) . . . . ? C2 C1 C6 N4 -176.5(8) . . . . ? N1 C1 C6 C5 176.3(8) . . . . ? C2 C1 C6 C5 57.0(10) . . . . ? C4 C5 C6 N4 174.6(10) . . . . ? C4 C5 C6 C1 -57.3(12) . . . . ? N2 C8 C9 C10 -175.4(11) . . . . ? C13 C8 C9 C10 1.8(16) . . . . ? C8 C9 C10 C11 -1.4(19) . . . . ? C9 C10 C11 C12 1(2) . . . . ? C9 C10 C11 N3 -178.3(12) . . . . ? C10 C11 C12 C13 -2(2) . . . . ? N3 C11 C12 C13 178.0(10) . . . . ? C11 C12 C13 C8 2.0(16) . . . . ? N2 C8 C13 C12 175.2(10) . . . . ? C9 C8 C13 C12 -2.1(15) . . . . ? C20 C15 C16 C17 -5.9(16) . . . . ? N5 C15 C16 C17 177.8(10) . . . . ? C15 C16 C17 C18 1(2) . . . . ? C16 C17 C18 C19 3(2) . . . . ? C16 C17 C18 N6 -179.7(12) . . . . ? C17 C18 C19 C20 -2.7(19) . . . . ? N6 C18 C19 C20 179.9(11) . . . . ? C18 C19 C20 C15 -1.7(18) . . . . ? C16 C15 C20 C19 6.0(15) . . . . ? N5 C15 C20 C19 -177.4(10) . . . . ? N7 C21 C22 C23 -176.7(14) . . . . ? C21 C22 C23 C24 -79(2) . . . . ? N7 C25 C26 C27 168(3) . . . . ? C25 C26 C27 C28 21(5) . . . . ? N7 C29 C30 C31 172.5(19) . . . . ? C29 C30 C31 C32 -162(2) . . . . ? N7 C33 C34 C35 179.5(16) . . . . ? C33 C34 C35 C36 60(4) . . . . ? N8 C37 C38 C39 -178.1(11) . . . . ? C37 C38 C39 C40 -173.3(12) . . . . ? N8 C41 C42 C43 169.3(13) . . . . ? C41 C42 C43 C44 -152(2) . . . . ? N8 C45 C46 C47 175.1(11) . . . . ? C45 C46 C47 C48 77(2) . . . . ? N8 C49 C50 C51 168.9(11) . . . . ? C49 C50 C51 C52 167.4(14) . . . . ? O1 C7 N1 C1 -2.9(14) . . . . ? N2 C7 N1 C1 178.7(7) . . . . ? C6 C1 N1 C7 151.0(8) . . . . ? C2 C1 N1 C7 -89.7(11) . . . . ? C9 C8 N2 C7 4.8(15) . . . . ? C13 C8 N2 C7 -172.4(9) . . . . ? O1 C7 N2 C8 -8.5(15) . . . . ? N1 C7 N2 C8 170.0(8) . . . . ? C10 C11 N3 O3 178.3(15) . . . . ? C12 C11 N3 O3 -1.4(19) . . . . ? C10 C11 N3 O2 -8(2) . . . . ? C12 C11 N3 O2 172.1(14) . . . . ? O4 C14 N4 C6 3.0(14) . . . . ? N5 C14 N4 C6 -176.2(8) . . . . ? C1 C6 N4 C14 -60.0(11) . . . . ? C5 C6 N4 C14 65.4(12) . . . . ? O4 C14 N5 C15 5.6(14) . . . . ? N4 C14 N5 C15 -175.2(8) . . . . ? C16 C15 N5 C14 -4.9(15) . . . . ? C20 C15 N5 C14 178.7(8) . . . . ? C19 C18 N6 O5 -170.4(15) . . . . ? C17 C18 N6 O5 12(2) . . . . ? C19 C18 N6 O6 5.9(19) . . . . ? C17 C18 N6 O6 -171.5(14) . . . . ? C22 C21 N7 C29 174.1(16) . . . . ? C22 C21 N7 C25 -66(2) . . . . ? C22 C21 N7 C33 48(2) . . . . ? C30 C29 N7 C21 61(3) . . . . ? C30 C29 N7 C25 -59(3) . . . . ? C30 C29 N7 C33 -174(2) . . . . ? C26 C25 N7 C21 -169(2) . . . . ? C26 C25 N7 C29 -47(3) . . . . ? C26 C25 N7 C33 73(2) . . . . ? C34 C33 N7 C21 67(2) . . . . ? C34 C33 N7 C29 -59(2) . . . . ? C34 C33 N7 C25 -176.6(19) . . . . ? C38 C37 N8 C41 66.0(13) . . . . ? C38 C37 N8 C49 -53.1(13) . . . . ? C38 C37 N8 C45 -171.9(10) . . . . ? C42 C41 N8 C37 58.4(14) . . . . ? C42 C41 N8 C49 -179.1(11) . . . . ? C42 C41 N8 C45 -61.6(13) . . . . ? C50 C49 N8 C37 -56.8(13) . . . . ? C50 C49 N8 C41 179.1(10) . . . . ? C50 C49 N8 C45 60.5(13) . . . . ? C46 C45 N8 C37 179.0(11) . . . . ? C46 C45 N8 C41 -56.7(13) . . . . ? C46 C45 N8 C49 58.6(13) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.28 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.299 _refine_diff_density_min -0.317 _refine_diff_density_rms 0.045