# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Piotr Przybylski' _publ_contact_author_email piotrp@amu.edu.pl loop_ _publ_author_name K.Pyta P.Przybylski B.Wicher M.Gdaniec J.Stefanska data_b23bx _database_code_depnum_ccdc_archive 'CCDC 859792' #TrackingRef '- 1-2CH3CCl3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ' rifampicin 1,1,1-trichloroethane solvate' _chemical_melting_point ? _chemical_formula_moiety 'C43 H58 N4 O12, 2(C2 H3 Cl3)' _chemical_formula_sum 'C47 H64 Cl6 N4 O12' _chemical_formula_weight 1089.72 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.9716(4) _cell_length_b 18.7546(6) _cell_length_c 13.2194(4) _cell_angle_alpha 90.00 _cell_angle_beta 101.595(3) _cell_angle_gamma 90.00 _cell_volume 2664.62(15) _cell_formula_units_Z 2 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 15280 _cell_measurement_theta_min 1.89 _cell_measurement_theta_max 28.07 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.358 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1144 _exptl_absorpt_coefficient_mu 0.384 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.881 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ; SCALE3 ABSPACK scaling algorithm (Oxford Diffraction, 2007) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(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 'Kuma KM4CCD \k geometry' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 21144 _diffrn_reflns_av_R_equivalents 0.0359 _diffrn_reflns_av_sigmaI/netI 0.0474 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 4.13 _diffrn_reflns_theta_max 25.03 _reflns_number_total 4837 _reflns_number_gt 3547 _reflns_threshold_expression I>2/s(I)) _computing_data_collection ; CrysAlis CCD (Oxford Diffraction, 2007) ; _computing_cell_refinement ; CrysAlis RED ; _computing_data_reduction ; CrysAlis RED (Oxford Diffraction, 2007) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; Ortep III for Windows (Farrugia, 1997) ; _computing_publication_material SHELXL-97 _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^)+(0.1102P)^2^+0.3937P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _chemical_absolute_configuration syn _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.06(10) _refine_ls_number_reflns 4837 _refine_ls_number_parameters 639 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0803 _refine_ls_R_factor_gt 0.0538 _refine_ls_wR_factor_ref 0.1652 _refine_ls_wR_factor_gt 0.1389 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.6516(4) 0.6065(2) 0.6584(3) 0.0263(10) Uani 1 1 d . . . H1 H 0.6123 0.5712 0.6743 0.039 Uiso 1 1 calc R . . O4 O 0.5098(4) 0.8567(2) 0.8221(3) 0.0300(10) Uani 1 1 d . . . H4O H 0.5448 0.8918 0.8008 0.045 Uiso 1 1 calc R . . O6 O 0.6968(4) 0.9231(2) 0.5113(3) 0.0237(9) Uani 1 1 d . . . O8 O 0.6979(4) 0.6731(2) 0.5057(3) 0.0293(10) Uani 1 1 d . . . H8 H 0.6805 0.6384 0.5404 0.044 Uiso 1 1 calc R . . O11 O 0.5787(4) 0.9671(2) 0.7334(3) 0.0300(10) Uani 1 1 d . . . O12 O 0.7860(4) 1.0102(2) 0.6298(3) 0.0264(10) Uani 1 1 d . . . O15 O 0.5093(5) 0.5201(2) 0.7129(3) 0.0373(11) Uani 1 1 d . . . O21 O 0.9385(4) 0.5862(2) 1.0874(3) 0.0267(9) Uani 1 1 d . . . H21 H 0.9925 0.6140 1.0728 0.040 Uiso 1 1 calc R . . O23 O 1.0908(3) 0.7036(2) 1.1102(3) 0.0221(9) Uani 1 1 d . . . H23O H 1.1550 0.7032 1.1572 0.033 Uiso 1 1 calc R . . O25 O 0.9856(4) 0.8928(2) 1.0645(3) 0.0289(10) Uani 1 1 d . . . O27 O 1.0733(4) 0.8797(3) 0.7848(3) 0.0342(11) Uani 1 1 d . . . O35 O 1.1938(5) 0.8882(3) 1.1108(4) 0.0428(12) Uani 1 1 d . . . N2 N 0.5462(4) 0.6039(2) 0.8409(4) 0.0202(10) Uani 1 1 d . . . H2N H 0.5267 0.6141 0.9022 0.030 Uiso 1 1 d R . . N38 N 0.4783(4) 0.6859(3) 0.9852(4) 0.0222(11) Uani 1 1 d . . . N39 N 0.4494(5) 0.6962(3) 1.0808(3) 0.0231(11) Uani 1 1 d . . . N40 N 0.3212(5) 0.7085(3) 1.2482(3) 0.0227(11) Uani 1 1 d . . . C1 C 0.6087(5) 0.6669(3) 0.6958(4) 0.0205(12) Uani 1 1 d . . . C2 C 0.5604(5) 0.6676(3) 0.7845(4) 0.0201(12) Uani 1 1 d . . . C3 C 0.5274(6) 0.7326(3) 0.8277(4) 0.0216(13) Uani 1 1 d . . . C4 C 0.5415(5) 0.7964(3) 0.7773(4) 0.0181(12) Uani 1 1 d . . . C5 C 0.6169(5) 0.8625(3) 0.6362(4) 0.0229(13) Uani 1 1 d . . . C6 C 0.6692(5) 0.8590(3) 0.5479(4) 0.0209(13) Uani 1 1 d . . . C7 C 0.6949(5) 0.7966(3) 0.5017(4) 0.0210(12) Uani 1 1 d . . . C8 C 0.6715(6) 0.7340(3) 0.5493(4) 0.0245(13) Uani 1 1 d . . . C9 C 0.6208(5) 0.7322(3) 0.6438(4) 0.0191(12) Uani 1 1 d . . . C10 C 0.5912(5) 0.7976(3) 0.6865(4) 0.0194(12) Uani 1 1 d . . . C11 C 0.6150(6) 0.9354(3) 0.6628(4) 0.0231(13) Uani 1 1 d . . . C12 C 0.6726(6) 0.9772(3) 0.5832(4) 0.0248(14) Uani 1 1 d . . . C13 C 0.5851(6) 1.0323(3) 0.5275(5) 0.0297(14) Uani 1 1 d . . . H13A H 0.6268 1.0595 0.4809 0.045 Uiso 1 1 calc R . . H13B H 0.5601 1.0647 0.5778 0.045 Uiso 1 1 calc R . . H13C H 0.5113 1.0088 0.4873 0.045 Uiso 1 1 calc R . . C14 C 0.7525(6) 0.7947(4) 0.4072(4) 0.0295(14) Uani 1 1 d . . . H14A H 0.8256 0.7635 0.4202 0.044 Uiso 1 1 calc R . . H14B H 0.7776 0.8429 0.3918 0.044 Uiso 1 1 calc R . . H14C H 0.6916 0.7764 0.3484 0.044 Uiso 1 1 calc R . . C15 C 0.5215(6) 0.5377(3) 0.8055(4) 0.0240(13) Uani 1 1 d . . . C16 C 0.5014(5) 0.4826(3) 0.8813(4) 0.0219(13) Uani 1 1 d . . . C17 C 0.5668(6) 0.4792(3) 0.9792(5) 0.0244(13) Uani 1 1 d . . . H17 H 0.5432 0.4420 1.0200 0.037 Uiso 1 1 calc R . . C18 C 0.6676(5) 0.5240(3) 1.0312(4) 0.0222(12) Uani 1 1 d . . . H18 H 0.7065 0.5558 0.9916 0.033 Uiso 1 1 calc R . . C19 C 0.7072(5) 0.5217(3) 1.1331(4) 0.0248(13) Uani 1 1 d . . . H19 H 0.6760 0.4835 1.1677 0.037 Uiso 1 1 calc R . . C20 C 0.7961(6) 0.5724(3) 1.2010(4) 0.0243(13) Uani 1 1 d . . . H20 H 0.8628 0.5436 1.2454 0.036 Uiso 1 1 calc R . . C21 C 0.8570(6) 0.6251(3) 1.1400(4) 0.0218(13) Uani 1 1 d . . . H21A H 0.7902 0.6473 1.0867 0.033 Uiso 1 1 calc R . . C22 C 0.9269(6) 0.6857(3) 1.2080(4) 0.0229(13) Uani 1 1 d . . . H22 H 0.8629 0.7134 1.2356 0.034 Uiso 1 1 calc R . . C23 C 0.9915(6) 0.7384(3) 1.1470(4) 0.0226(13) Uani 1 1 d . . . H23 H 1.0275 0.7781 1.1942 0.034 Uiso 1 1 calc R . . C24 C 0.9071(6) 0.7708(3) 1.0509(4) 0.0231(13) Uani 1 1 d . . . H24 H 0.8829 0.7319 0.9991 0.035 Uiso 1 1 calc R . . C25 C 0.9785(6) 0.8281(3) 1.0023(4) 0.0220(13) Uani 1 1 d . . . H25 H 1.0647 0.8105 1.0027 0.033 Uiso 1 1 calc R . . C26 C 0.9169(6) 0.8501(3) 0.8916(4) 0.0257(13) Uani 1 1 d . . . H26 H 0.8347 0.8717 0.8955 0.039 Uiso 1 1 calc R . . C27 C 0.9912(6) 0.9080(3) 0.8459(5) 0.0286(14) Uani 1 1 d . . . H27 H 1.0417 0.9357 0.9043 0.043 Uiso 1 1 calc R . . C28 C 0.9007(6) 0.9573(4) 0.7825(5) 0.0333(15) Uani 1 1 d . . . H28 H 0.8570 0.9886 0.8192 0.050 Uiso 1 1 calc R . . C29 C 0.8745(6) 0.9624(3) 0.6811(5) 0.0289(14) Uani 1 1 d . . . H29 H 0.9172 0.9325 0.6417 0.043 Uiso 1 1 calc R . . C30 C 0.4036(6) 0.4292(4) 0.8388(5) 0.0362(17) Uani 1 1 d . . . H30A H 0.4018 0.3917 0.8901 0.054 Uiso 1 1 calc R . . H30B H 0.4224 0.4080 0.7759 0.054 Uiso 1 1 calc R . . H30C H 0.3224 0.4529 0.8224 0.054 Uiso 1 1 calc R . . C31 C 0.7175(6) 0.6093(4) 1.2719(5) 0.0297(14) Uani 1 1 d . . . H31A H 0.7733 0.6325 1.3297 0.045 Uiso 1 1 calc R . . H31B H 0.6670 0.5735 1.2985 0.045 Uiso 1 1 calc R . . H31C H 0.6629 0.6451 1.2320 0.045 Uiso 1 1 calc R . . C32 C 1.0197(6) 0.6576(3) 1.3010(4) 0.0255(13) Uani 1 1 d . . . H32A H 1.0640 0.6977 1.3394 0.038 Uiso 1 1 calc R . . H32B H 1.0795 0.6261 1.2773 0.038 Uiso 1 1 calc R . . H32C H 0.9752 0.6309 1.3460 0.038 Uiso 1 1 calc R . . C33 C 0.7866(6) 0.8024(4) 1.0767(5) 0.0312(14) Uani 1 1 d . . . H33A H 0.7351 0.7637 1.0952 0.047 Uiso 1 1 calc R . . H33B H 0.7403 0.8279 1.0164 0.047 Uiso 1 1 calc R . . H33C H 0.8081 0.8355 1.1349 0.047 Uiso 1 1 calc R . . C34 C 0.8895(7) 0.7851(4) 0.8197(5) 0.0337(16) Uani 1 1 d . . . H34A H 0.8237 0.7563 0.8397 0.051 Uiso 1 1 calc R . . H34B H 0.9651 0.7563 0.8253 0.051 Uiso 1 1 calc R . . H34C H 0.8623 0.8013 0.7483 0.051 Uiso 1 1 calc R . . C35 C 1.0983(7) 0.9186(4) 1.1107(5) 0.0311(15) Uani 1 1 d . . . C36 C 1.0867(8) 0.9900(4) 1.1568(6) 0.048(2) Uani 1 1 d . . . H36A H 1.1617 1.0001 1.2089 0.072 Uiso 1 1 calc R . . H36B H 1.0139 0.9906 1.1893 0.072 Uiso 1 1 calc R . . H36C H 1.0768 1.0264 1.1025 0.072 Uiso 1 1 calc R . . C37 C 1.1797(6) 0.8449(4) 0.8425(5) 0.0347(16) Uani 1 1 d . . . H37A H 1.2421 0.8392 0.7995 0.052 Uiso 1 1 calc R . . H37B H 1.1558 0.7979 0.8645 0.052 Uiso 1 1 calc R . . H37C H 1.2146 0.8736 0.9035 0.052 Uiso 1 1 calc R . . C38 C 0.4818(5) 0.7380(3) 0.9243(4) 0.0216(13) Uani 1 1 d . . . H38 H 0.4531 0.7831 0.9425 0.032 Uiso 1 1 calc R . . C39 C 0.3934(6) 0.7641(3) 1.1022(4) 0.0245(13) Uani 1 1 d . . . H39A H 0.3082 0.7678 1.0601 0.037 Uiso 1 1 calc R . . H39B H 0.4433 0.8042 1.0836 0.037 Uiso 1 1 calc R . . C40 C 0.3890(6) 0.7680(3) 1.2156(4) 0.0255(13) Uani 1 1 d . . . H40A H 0.4750 0.7682 1.2568 0.038 Uiso 1 1 calc R . . H40B H 0.3487 0.8132 1.2293 0.038 Uiso 1 1 calc R . . C41 C 0.3792(6) 0.6411(3) 1.2263(4) 0.0252(13) Uani 1 1 d . . . H41A H 0.3302 0.6006 1.2451 0.038 Uiso 1 1 calc R . . H41B H 0.4642 0.6381 1.2691 0.038 Uiso 1 1 calc R . . C42 C 0.3861(6) 0.6354(3) 1.1139(4) 0.0261(13) Uani 1 1 d . . . H42A H 0.4309 0.5913 1.1027 0.039 Uiso 1 1 calc R . . H42B H 0.3008 0.6324 1.0717 0.039 Uiso 1 1 calc R . . C43 C 0.3234(6) 0.7136(4) 1.3593(4) 0.0289(15) Uani 1 1 d . . . H43A H 0.2800 0.7571 1.3734 0.043 Uiso 1 1 calc R . . H43B H 0.4098 0.7153 1.3973 0.043 Uiso 1 1 calc R . . H43C H 0.2817 0.6719 1.3816 0.043 Uiso 1 1 calc R . . C1B C 0.8024(7) 0.4184(4) 0.5110(5) 0.0437(18) Uani 1 1 d . . . C2B C 0.7325(14) 0.3882(8) 0.4083(8) 0.134(7) Uani 1 1 d . . . H2B1 H 0.7918 0.3658 0.3717 0.202 Uiso 1 1 calc R . . H2B2 H 0.6886 0.4268 0.3661 0.202 Uiso 1 1 calc R . . H2B3 H 0.6722 0.3525 0.4213 0.202 Uiso 1 1 calc R . . Cl3B Cl 0.8439(2) 0.50949(12) 0.5064(2) 0.0723(7) Uani 1 1 d . . . Cl2B Cl 0.6895(2) 0.41390(13) 0.59167(18) 0.0686(7) Uani 1 1 d . . . Cl1B Cl 0.9318(3) 0.36939(17) 0.5676(3) 0.0968(10) Uani 1 1 d . . . C1A C 0.1534(7) 0.6297(5) 0.6667(6) 0.0448(18) Uani 1 1 d . . . C2A C 0.1608(6) 0.5515(4) 0.6276(5) 0.0315(15) Uani 1 1 d . . . H2BA H 0.1350 0.5503 0.5523 0.047 Uiso 1 1 calc R . . H2BB H 0.1055 0.5209 0.6585 0.047 Uiso 1 1 calc R . . H2BC H 0.2465 0.5341 0.6477 0.047 Uiso 1 1 calc R . . Cl1A Cl 0.1921(3) 0.63008(15) 0.80358(17) 0.0739(7) Uani 1 1 d . . . Cl2A Cl 0.2601(2) 0.68580(12) 0.61996(19) 0.0648(6) Uani 1 1 d . . . Cl3A Cl 0.0027(2) 0.66360(16) 0.6253(2) 0.0850(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.036(3) 0.017(2) 0.028(2) -0.0004(17) 0.0114(19) 0.0009(19) O4 0.042(3) 0.016(2) 0.037(2) 0.0019(18) 0.021(2) 0.001(2) O6 0.034(2) 0.018(2) 0.020(2) 0.0019(16) 0.0080(17) -0.0007(19) O8 0.040(3) 0.023(2) 0.027(2) -0.0051(18) 0.0126(19) -0.004(2) O11 0.044(3) 0.021(2) 0.029(2) 0.0018(17) 0.018(2) -0.001(2) O12 0.029(2) 0.026(2) 0.022(2) 0.0073(17) -0.0018(17) -0.008(2) O15 0.059(3) 0.029(2) 0.023(2) -0.0044(19) 0.007(2) -0.018(2) O21 0.028(2) 0.025(2) 0.031(2) -0.0047(17) 0.0146(19) -0.0005(19) O23 0.015(2) 0.027(2) 0.024(2) 0.0010(17) 0.0047(16) 0.0025(18) O25 0.033(3) 0.021(2) 0.032(2) -0.0002(17) 0.004(2) 0.0029(19) O27 0.034(3) 0.043(3) 0.026(2) 0.004(2) 0.004(2) 0.000(2) O35 0.033(3) 0.038(3) 0.051(3) -0.007(2) -0.005(2) 0.001(2) N2 0.022(3) 0.020(3) 0.021(2) -0.0001(19) 0.009(2) -0.005(2) N38 0.021(3) 0.023(3) 0.025(2) 0.001(2) 0.010(2) 0.000(2) N39 0.028(3) 0.025(3) 0.018(2) 0.002(2) 0.010(2) 0.003(2) N40 0.025(3) 0.024(3) 0.021(2) -0.001(2) 0.009(2) 0.001(2) C1 0.018(3) 0.020(3) 0.022(3) -0.002(2) 0.002(2) -0.003(2) C2 0.018(3) 0.021(3) 0.020(3) 0.005(2) 0.000(2) -0.006(3) C3 0.025(3) 0.026(3) 0.014(3) 0.001(2) 0.003(2) 0.002(3) C4 0.018(3) 0.019(3) 0.018(3) -0.003(2) 0.006(2) 0.003(3) C5 0.021(3) 0.023(3) 0.025(3) -0.003(2) 0.006(2) 0.002(3) C6 0.017(3) 0.024(3) 0.021(3) 0.002(2) 0.002(2) -0.005(3) C7 0.020(3) 0.022(3) 0.020(3) -0.001(2) 0.003(2) -0.001(3) C8 0.028(4) 0.024(3) 0.019(3) -0.001(2) -0.001(2) 0.002(3) C9 0.016(3) 0.019(3) 0.021(3) 0.001(2) 0.001(2) -0.004(2) C10 0.018(3) 0.019(3) 0.019(3) 0.001(2) -0.001(2) -0.004(3) C11 0.025(3) 0.023(3) 0.019(3) 0.003(2) -0.004(2) 0.000(3) C12 0.029(4) 0.022(3) 0.022(3) 0.000(2) 0.002(3) -0.006(3) C13 0.035(4) 0.029(3) 0.023(3) 0.008(3) -0.001(3) 0.002(3) C14 0.042(4) 0.027(3) 0.022(3) 0.002(3) 0.010(3) -0.007(3) C15 0.024(3) 0.022(3) 0.024(3) 0.003(2) 0.001(3) -0.004(3) C16 0.018(3) 0.021(3) 0.028(3) 0.007(2) 0.008(3) -0.001(3) C17 0.022(3) 0.023(3) 0.029(3) 0.002(2) 0.007(3) -0.002(3) C18 0.022(3) 0.017(3) 0.027(3) 0.003(2) 0.004(2) 0.002(3) C19 0.029(4) 0.020(3) 0.027(3) 0.001(2) 0.010(3) 0.001(3) C20 0.026(3) 0.027(3) 0.021(3) 0.003(2) 0.007(3) 0.007(3) C21 0.023(3) 0.021(3) 0.021(3) -0.004(2) 0.004(2) 0.001(3) C22 0.022(3) 0.026(3) 0.022(3) 0.001(2) 0.009(2) 0.002(3) C23 0.020(3) 0.024(3) 0.022(3) -0.001(2) 0.001(2) 0.006(3) C24 0.018(3) 0.023(3) 0.027(3) -0.001(2) 0.002(2) 0.001(3) C25 0.026(3) 0.018(3) 0.021(3) -0.002(2) 0.003(2) -0.001(3) C26 0.021(3) 0.028(3) 0.027(3) 0.003(3) 0.002(3) 0.001(3) C27 0.029(4) 0.033(4) 0.023(3) 0.010(3) 0.003(3) 0.002(3) C28 0.028(4) 0.031(4) 0.040(4) -0.001(3) 0.002(3) -0.007(3) C29 0.025(3) 0.027(3) 0.034(3) 0.013(3) 0.004(3) -0.002(3) C30 0.038(4) 0.028(4) 0.039(4) 0.013(3) -0.002(3) -0.013(3) C31 0.023(3) 0.033(4) 0.035(3) 0.003(3) 0.010(3) -0.001(3) C32 0.020(3) 0.034(4) 0.022(3) -0.001(2) 0.003(2) -0.002(3) C33 0.024(3) 0.032(4) 0.036(3) 0.005(3) 0.004(3) 0.008(3) C34 0.032(4) 0.033(4) 0.032(3) 0.002(3) -0.002(3) -0.005(3) C35 0.035(4) 0.027(3) 0.030(3) -0.003(3) 0.004(3) -0.005(3) C36 0.059(5) 0.038(4) 0.046(4) -0.006(3) 0.006(4) -0.003(4) C37 0.034(4) 0.040(4) 0.031(3) 0.004(3) 0.010(3) 0.003(3) C38 0.025(3) 0.019(3) 0.021(3) -0.001(2) 0.006(2) 0.000(3) C39 0.024(3) 0.026(3) 0.024(3) 0.003(2) 0.008(3) 0.006(3) C40 0.025(3) 0.027(3) 0.025(3) -0.003(3) 0.006(3) 0.003(3) C41 0.024(3) 0.025(3) 0.028(3) 0.007(2) 0.009(3) 0.006(3) C42 0.031(4) 0.022(3) 0.028(3) 0.002(3) 0.014(3) -0.001(3) C43 0.032(4) 0.035(4) 0.021(3) 0.003(3) 0.007(3) 0.000(3) C1B 0.044(4) 0.044(4) 0.042(4) 0.000(3) 0.006(3) -0.003(4) C2B 0.159(12) 0.145(13) 0.063(7) -0.072(8) -0.064(7) 0.078(10) Cl3B 0.0746(16) 0.0491(13) 0.0899(17) 0.0101(12) 0.0084(13) -0.0048(12) Cl2B 0.0846(18) 0.0646(15) 0.0647(14) 0.0175(11) 0.0343(13) 0.0171(13) Cl1B 0.0614(16) 0.0842(19) 0.139(3) 0.0311(18) 0.0066(16) 0.0331(15) C1A 0.034(4) 0.054(5) 0.043(4) -0.004(4) 0.001(3) 0.000(4) C2A 0.017(3) 0.042(4) 0.038(3) -0.023(3) 0.011(3) -0.001(3) Cl1A 0.0912(18) 0.0815(17) 0.0441(11) -0.0106(11) 0.0020(11) -0.0038(15) Cl2A 0.0627(14) 0.0565(14) 0.0753(14) -0.0022(11) 0.0141(11) -0.0067(11) Cl3A 0.0559(14) 0.096(2) 0.0983(19) -0.0285(16) 0.0031(13) 0.0232(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.357(7) . ? O1 H1 0.8400 . ? O4 C4 1.355(7) . ? O4 H4O 0.8400 . ? O6 C6 1.352(7) . ? O6 C12 1.452(7) . ? O8 C8 1.337(7) . ? O8 H8 0.8400 . ? O11 C11 1.238(7) . ? O12 C29 1.393(7) . ? O12 C12 1.415(7) . ? O15 C15 1.249(7) . ? O21 C21 1.437(7) . ? O21 H21 0.8400 . ? O23 C23 1.437(7) . ? O23 H23O 0.8400 . ? O25 C35 1.354(8) . ? O25 C25 1.460(7) . ? O27 C37 1.418(8) . ? O27 C27 1.428(8) . ? O35 C35 1.193(8) . ? N2 C15 1.335(8) . ? N2 C2 1.432(7) . ? N2 H2N 0.9000 . ? N38 C38 1.272(7) . ? N38 N39 1.377(7) . ? N39 C42 1.448(8) . ? N39 C39 1.464(8) . ? N40 C40 1.454(8) . ? N40 C43 1.467(7) . ? N40 C41 1.471(8) . ? C1 C2 1.381(8) . ? C1 C9 1.424(8) . ? C2 C3 1.423(8) . ? C3 C4 1.393(8) . ? C3 C38 1.466(8) . ? C4 C10 1.416(8) . ? C5 C6 1.401(8) . ? C5 C11 1.412(9) . ? C5 C10 1.441(8) . ? C6 C7 1.377(8) . ? C7 C8 1.380(9) . ? C7 C14 1.509(8) . ? C8 C9 1.466(8) . ? C9 C10 1.415(8) . ? C11 C12 1.546(8) . ? C12 C13 1.499(9) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C16 1.487(8) . ? C16 C17 1.349(8) . ? C16 C30 1.492(9) . ? C17 C18 1.448(8) . ? C17 H17 0.9500 . ? C18 C19 1.330(8) . ? C18 H18 0.9500 . ? C19 C20 1.520(9) . ? C19 H19 0.9500 . ? C20 C21 1.513(8) . ? C20 C31 1.556(9) . ? C20 H20 1.0000 . ? C21 C22 1.553(8) . ? C21 H21A 1.0000 . ? C22 C32 1.524(8) . ? C22 C23 1.536(9) . ? C22 H22 1.0000 . ? C23 C24 1.539(8) . ? C23 H23 1.0000 . ? C24 C25 1.543(8) . ? C24 C33 1.548(9) . ? C24 H24 1.0000 . ? C25 C26 1.540(8) . ? C25 H25 1.0000 . ? C26 C34 1.537(9) . ? C26 C27 1.551(9) . ? C26 H26 1.0000 . ? C27 C28 1.487(9) . ? C27 H27 1.0000 . ? C28 C29 1.317(9) . ? C28 H28 0.9500 . ? C29 H29 0.9500 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? C35 C36 1.487(10) . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? C38 H38 0.9500 . ? C39 C40 1.512(8) . ? C39 H39A 0.9900 . ? C39 H39B 0.9900 . ? C40 H40A 0.9900 . ? C40 H40B 0.9900 . ? C41 C42 1.506(8) . ? C41 H41A 0.9900 . ? C41 H41B 0.9900 . ? C42 H42A 0.9900 . ? C42 H42B 0.9900 . ? C43 H43A 0.9800 . ? C43 H43B 0.9800 . ? C43 H43C 0.9800 . ? C1B C2B 1.527(11) . ? C1B Cl1B 1.731(8) . ? C1B Cl3B 1.772(8) . ? C1B Cl2B 1.792(8) . ? C2B H2B1 0.9800 . ? C2B H2B2 0.9800 . ? C2B H2B3 0.9800 . ? C1A C2A 1.563(10) . ? C1A Cl3A 1.753(8) . ? C1A Cl1A 1.773(8) . ? C1A Cl2A 1.776(8) . ? C2A H2BA 0.9800 . ? C2A H2BB 0.9800 . ? C2A H2BC 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 H1 109.5 . . ? C4 O4 H4O 109.5 . . ? C6 O6 C12 107.6(4) . . ? C8 O8 H8 109.5 . . ? C29 O12 C12 113.4(5) . . ? C21 O21 H21 109.5 . . ? C23 O23 H23O 109.5 . . ? C35 O25 C25 119.4(5) . . ? C37 O27 C27 114.3(4) . . ? C15 N2 C2 129.0(5) . . ? C15 N2 H2N 116.4 . . ? C2 N2 H2N 111.3 . . ? C38 N38 N39 120.9(5) . . ? N38 N39 C42 112.3(4) . . ? N38 N39 C39 118.9(4) . . ? C42 N39 C39 112.4(4) . . ? C40 N40 C43 109.9(5) . . ? C40 N40 C41 109.5(4) . . ? C43 N40 C41 109.4(5) . . ? O1 C1 C2 122.5(5) . . ? O1 C1 C9 118.0(5) . . ? C2 C1 C9 119.4(5) . . ? C1 C2 C3 121.3(5) . . ? C1 C2 N2 122.3(5) . . ? C3 C2 N2 116.3(5) . . ? C4 C3 C2 118.8(5) . . ? C4 C3 C38 116.6(5) . . ? C2 C3 C38 124.6(5) . . ? O4 C4 C3 116.4(5) . . ? O4 C4 C10 122.2(5) . . ? C3 C4 C10 121.3(5) . . ? C6 C5 C11 106.4(5) . . ? C6 C5 C10 119.7(5) . . ? C11 C5 C10 133.5(5) . . ? O6 C6 C7 121.1(5) . . ? O6 C6 C5 114.6(5) . . ? C7 C6 C5 124.4(5) . . ? C6 C7 C8 116.6(5) . . ? C6 C7 C14 123.0(5) . . ? C8 C7 C14 120.3(5) . . ? O8 C8 C7 116.9(5) . . ? O8 C8 C9 120.1(5) . . ? C7 C8 C9 123.0(5) . . ? C10 C9 C1 120.2(5) . . ? C10 C9 C8 118.5(5) . . ? C1 C9 C8 121.2(5) . . ? C9 C10 C4 118.8(5) . . ? C9 C10 C5 117.8(5) . . ? C4 C10 C5 123.4(5) . . ? O11 C11 C5 132.5(6) . . ? O11 C11 C12 120.5(5) . . ? C5 C11 C12 107.0(5) . . ? O12 C12 O6 109.3(5) . . ? O12 C12 C13 109.4(5) . . ? O6 C12 C13 110.1(5) . . ? O12 C12 C11 111.7(4) . . ? O6 C12 C11 104.2(4) . . ? C13 C12 C11 112.0(5) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C7 C14 H14A 109.5 . . ? C7 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C7 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O15 C15 N2 124.3(5) . . ? O15 C15 C16 118.4(5) . . ? N2 C15 C16 117.3(5) . . ? C17 C16 C15 123.8(5) . . ? C17 C16 C30 122.3(5) . . ? C15 C16 C30 113.9(5) . . ? C16 C17 C18 129.6(6) . . ? C16 C17 H17 115.2 . . ? C18 C17 H17 115.2 . . ? C19 C18 C17 121.6(6) . . ? C19 C18 H18 119.2 . . ? C17 C18 H18 119.2 . . ? C18 C19 C20 128.2(5) . . ? C18 C19 H19 115.9 . . ? C20 C19 H19 115.9 . . ? C21 C20 C19 113.2(5) . . ? C21 C20 C31 112.8(5) . . ? C19 C20 C31 105.5(5) . . ? C21 C20 H20 108.4 . . ? C19 C20 H20 108.4 . . ? C31 C20 H20 108.4 . . ? O21 C21 C20 108.1(5) . . ? O21 C21 C22 111.6(5) . . ? C20 C21 C22 112.9(5) . . ? O21 C21 H21A 108.0 . . ? C20 C21 H21A 108.0 . . ? C22 C21 H21A 108.0 . . ? C32 C22 C23 110.0(5) . . ? C32 C22 C21 112.6(5) . . ? C23 C22 C21 113.2(4) . . ? C32 C22 H22 106.8 . . ? C23 C22 H22 106.8 . . ? C21 C22 H22 106.8 . . ? O23 C23 C22 110.3(5) . . ? O23 C23 C24 105.7(4) . . ? C22 C23 C24 115.0(5) . . ? O23 C23 H23 108.5 . . ? C22 C23 H23 108.5 . . ? C24 C23 H23 108.5 . . ? C23 C24 C25 110.3(5) . . ? C23 C24 C33 111.6(5) . . ? C25 C24 C33 110.7(5) . . ? C23 C24 H24 108.0 . . ? C25 C24 H24 108.0 . . ? C33 C24 H24 108.0 . . ? O25 C25 C26 106.0(5) . . ? O25 C25 C24 108.5(5) . . ? C26 C25 C24 114.8(5) . . ? O25 C25 H25 109.1 . . ? C26 C25 H25 109.1 . . ? C24 C25 H25 109.1 . . ? C34 C26 C25 111.6(5) . . ? C34 C26 C27 111.6(5) . . ? C25 C26 C27 113.1(5) . . ? C34 C26 H26 106.7 . . ? C25 C26 H26 106.7 . . ? C27 C26 H26 106.7 . . ? O27 C27 C28 109.8(5) . . ? O27 C27 C26 113.6(5) . . ? C28 C27 C26 108.1(5) . . ? O27 C27 H27 108.4 . . ? C28 C27 H27 108.4 . . ? C26 C27 H27 108.4 . . ? C29 C28 C27 127.1(7) . . ? C29 C28 H28 116.4 . . ? C27 C28 H28 116.4 . . ? C28 C29 O12 122.0(6) . . ? C28 C29 H29 119.0 . . ? O12 C29 H29 119.0 . . ? C16 C30 H30A 109.5 . . ? C16 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C16 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C20 C31 H31A 109.5 . . ? C20 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C20 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C22 C32 H32A 109.5 . . ? C22 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C22 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C24 C33 H33A 109.5 . . ? C24 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C24 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C26 C34 H34A 109.5 . . ? C26 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C26 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? O35 C35 O25 123.5(6) . . ? O35 C35 C36 125.3(7) . . ? O25 C35 C36 111.1(7) . . ? 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 . . ? O27 C37 H37A 109.5 . . ? O27 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? O27 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? N38 C38 C3 123.9(5) . . ? N38 C38 H38 118.1 . . ? C3 C38 H38 118.1 . . ? N39 C39 C40 109.4(5) . . ? N39 C39 H39A 109.8 . . ? C40 C39 H39A 109.8 . . ? N39 C39 H39B 109.8 . . ? C40 C39 H39B 109.8 . . ? H39A C39 H39B 108.2 . . ? N40 C40 C39 112.2(5) . . ? N40 C40 H40A 109.2 . . ? C39 C40 H40A 109.2 . . ? N40 C40 H40B 109.2 . . ? C39 C40 H40B 109.2 . . ? H40A C40 H40B 107.9 . . ? N40 C41 C42 111.4(5) . . ? N40 C41 H41A 109.4 . . ? C42 C41 H41A 109.4 . . ? N40 C41 H41B 109.4 . . ? C42 C41 H41B 109.4 . . ? H41A C41 H41B 108.0 . . ? N39 C42 C41 111.4(5) . . ? N39 C42 H42A 109.3 . . ? C41 C42 H42A 109.3 . . ? N39 C42 H42B 109.3 . . ? C41 C42 H42B 109.3 . . ? H42A C42 H42B 108.0 . . ? N40 C43 H43A 109.5 . . ? N40 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? N40 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? C2B C1B Cl1B 114.2(7) . . ? C2B C1B Cl3B 114.5(8) . . ? Cl1B C1B Cl3B 109.4(4) . . ? C2B C1B Cl2B 103.2(8) . . ? Cl1B C1B Cl2B 108.8(4) . . ? Cl3B C1B Cl2B 106.2(4) . . ? C1B C2B H2B1 109.5 . . ? C1B C2B H2B2 109.5 . . ? H2B1 C2B H2B2 109.5 . . ? C1B C2B H2B3 109.5 . . ? H2B1 C2B H2B3 109.5 . . ? H2B2 C2B H2B3 109.5 . . ? C2A C1A Cl3A 110.2(5) . . ? C2A C1A Cl1A 108.9(5) . . ? Cl3A C1A Cl1A 109.6(4) . . ? C2A C1A Cl2A 111.1(5) . . ? Cl3A C1A Cl2A 108.8(5) . . ? Cl1A C1A Cl2A 108.2(4) . . ? C1A C2A H2BA 109.5 . . ? C1A C2A H2BB 109.5 . . ? H2BA C2A H2BB 109.5 . . ? C1A C2A H2BC 109.5 . . ? H2BA C2A H2BC 109.5 . . ? H2BB C2A H2BC 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 C38 N38 N39 C42 148.8(5) . . . . ? C38 N38 N39 C39 14.7(8) . . . . ? O1 C1 C2 C3 173.8(5) . . . . ? C9 C1 C2 C3 -2.8(8) . . . . ? O1 C1 C2 N2 -3.2(9) . . . . ? C9 C1 C2 N2 -179.7(5) . . . . ? C15 N2 C2 C1 -32.2(9) . . . . ? C15 N2 C2 C3 150.7(6) . . . . ? C1 C2 C3 C4 1.7(8) . . . . ? N2 C2 C3 C4 178.8(5) . . . . ? C1 C2 C3 C38 -176.7(5) . . . . ? N2 C2 C3 C38 0.4(8) . . . . ? C2 C3 C4 O4 -179.5(5) . . . . ? C38 C3 C4 O4 -1.0(8) . . . . ? C2 C3 C4 C10 -1.9(8) . . . . ? C38 C3 C4 C10 176.6(5) . . . . ? C12 O6 C6 C7 -173.3(5) . . . . ? C12 O6 C6 C5 5.1(6) . . . . ? C11 C5 C6 O6 -2.8(7) . . . . ? C10 C5 C6 O6 -175.9(5) . . . . ? C11 C5 C6 C7 175.5(5) . . . . ? C10 C5 C6 C7 2.4(9) . . . . ? O6 C6 C7 C8 175.4(5) . . . . ? C5 C6 C7 C8 -2.8(8) . . . . ? O6 C6 C7 C14 -1.2(9) . . . . ? C5 C6 C7 C14 -179.4(6) . . . . ? C6 C7 C8 O8 -179.1(5) . . . . ? C14 C7 C8 O8 -2.4(8) . . . . ? C6 C7 C8 C9 0.6(8) . . . . ? C14 C7 C8 C9 177.3(5) . . . . ? O1 C1 C9 C10 -172.5(5) . . . . ? C2 C1 C9 C10 4.2(8) . . . . ? O1 C1 C9 C8 3.3(8) . . . . ? C2 C1 C9 C8 -180.0(5) . . . . ? O8 C8 C9 C10 -178.6(5) . . . . ? C7 C8 C9 C10 1.8(9) . . . . ? O8 C8 C9 C1 5.5(9) . . . . ? C7 C8 C9 C1 -174.1(6) . . . . ? C1 C9 C10 C4 -4.4(8) . . . . ? C8 C9 C10 C4 179.7(5) . . . . ? C1 C9 C10 C5 173.9(5) . . . . ? C8 C9 C10 C5 -2.1(8) . . . . ? O4 C4 C10 C9 -179.3(5) . . . . ? C3 C4 C10 C9 3.2(8) . . . . ? O4 C4 C10 C5 2.6(9) . . . . ? C3 C4 C10 C5 -174.9(5) . . . . ? C6 C5 C10 C9 0.2(8) . . . . ? C11 C5 C10 C9 -170.7(6) . . . . ? C6 C5 C10 C4 178.3(5) . . . . ? C11 C5 C10 C4 7.5(10) . . . . ? C6 C5 C11 O11 -179.9(6) . . . . ? C10 C5 C11 O11 -8.2(12) . . . . ? C6 C5 C11 C12 -0.6(6) . . . . ? C10 C5 C11 C12 171.1(6) . . . . ? C29 O12 C12 O6 -57.7(6) . . . . ? C29 O12 C12 C13 -178.3(5) . . . . ? C29 O12 C12 C11 57.0(6) . . . . ? C6 O6 C12 O12 114.5(5) . . . . ? C6 O6 C12 C13 -125.2(5) . . . . ? C6 O6 C12 C11 -5.0(6) . . . . ? O11 C11 C12 O12 65.0(7) . . . . ? C5 C11 C12 O12 -114.4(5) . . . . ? O11 C11 C12 O6 -177.2(5) . . . . ? C5 C11 C12 O6 3.4(6) . . . . ? O11 C11 C12 C13 -58.2(7) . . . . ? C5 C11 C12 C13 122.4(5) . . . . ? C2 N2 C15 O15 2.0(10) . . . . ? C2 N2 C15 C16 -175.1(5) . . . . ? O15 C15 C16 C17 144.4(6) . . . . ? N2 C15 C16 C17 -38.4(9) . . . . ? O15 C15 C16 C30 -34.1(8) . . . . ? N2 C15 C16 C30 143.1(6) . . . . ? C15 C16 C17 C18 -1.5(10) . . . . ? C30 C16 C17 C18 176.9(6) . . . . ? C16 C17 C18 C19 167.6(6) . . . . ? C17 C18 C19 C20 -169.3(6) . . . . ? C18 C19 C20 C21 -8.6(9) . . . . ? C18 C19 C20 C31 115.2(7) . . . . ? C19 C20 C21 O21 -67.2(6) . . . . ? C31 C20 C21 O21 173.1(5) . . . . ? C19 C20 C21 C22 168.8(5) . . . . ? C31 C20 C21 C22 49.1(7) . . . . ? O21 C21 C22 C32 -69.0(6) . . . . ? C20 C21 C22 C32 53.0(7) . . . . ? O21 C21 C22 C23 56.6(6) . . . . ? C20 C21 C22 C23 178.7(5) . . . . ? C32 C22 C23 O23 60.6(6) . . . . ? C21 C22 C23 O23 -66.4(6) . . . . ? C32 C22 C23 C24 -179.9(5) . . . . ? C21 C22 C23 C24 53.1(7) . . . . ? O23 C23 C24 C25 -63.5(6) . . . . ? C22 C23 C24 C25 174.5(5) . . . . ? O23 C23 C24 C33 173.0(5) . . . . ? C22 C23 C24 C33 51.0(7) . . . . ? C35 O25 C25 C26 -117.3(5) . . . . ? C35 O25 C25 C24 118.9(6) . . . . ? C23 C24 C25 O25 -76.9(6) . . . . ? C33 C24 C25 O25 47.1(6) . . . . ? C23 C24 C25 C26 164.7(5) . . . . ? C33 C24 C25 C26 -71.3(6) . . . . ? O25 C25 C26 C34 -173.3(5) . . . . ? C24 C25 C26 C34 -53.5(7) . . . . ? O25 C25 C26 C27 59.9(6) . . . . ? C24 C25 C26 C27 179.6(5) . . . . ? C37 O27 C27 C28 166.7(5) . . . . ? C37 O27 C27 C26 -72.1(6) . . . . ? C34 C26 C27 O27 -31.8(7) . . . . ? C25 C26 C27 O27 95.1(6) . . . . ? C34 C26 C27 C28 90.3(6) . . . . ? C25 C26 C27 C28 -142.8(5) . . . . ? O27 C27 C28 C29 16.4(9) . . . . ? C26 C27 C28 C29 -108.0(7) . . . . ? C27 C28 C29 O12 179.0(6) . . . . ? C12 O12 C29 C28 -104.5(7) . . . . ? C25 O25 C35 O35 -6.4(9) . . . . ? C25 O25 C35 C36 171.4(5) . . . . ? N39 N38 C38 C3 171.7(5) . . . . ? C4 C3 C38 N38 -171.2(6) . . . . ? C2 C3 C38 N38 7.2(9) . . . . ? N38 N39 C39 C40 -171.0(5) . . . . ? C42 N39 C39 C40 54.9(6) . . . . ? C43 N40 C40 C39 178.1(5) . . . . ? C41 N40 C40 C39 57.8(6) . . . . ? N39 C39 C40 N40 -57.0(6) . . . . ? C40 N40 C41 C42 -56.0(6) . . . . ? C43 N40 C41 C42 -176.6(5) . . . . ? N38 N39 C42 C41 168.1(5) . . . . ? C39 N39 C42 C41 -54.8(6) . . . . ? N40 C41 C42 N39 54.9(7) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O8 H8 O1 0.84 1.76 2.510(6) 148 . O21 H21 O23 0.84 2.01 2.744(6) 146 . O4 H4O O11 0.84 1.75 2.567(6) 164 . N2 H2N N38 0.90 1.88 2.670(7) 145 . O1 H1 O15 0.84 1.64 2.457(6) 164 . O23 H23O N40 0.84 1.98 2.806(6) 170 1_655 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.763 _refine_diff_density_min -0.544 _refine_diff_density_rms 0.071 # Attachment '- 2MeOH_3H2O.cif' data_x _database_code_depnum_ccdc_archive 'CCDC 859793' #TrackingRef '- 2MeOH_3H2O.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'rifampicin methanol trisolvate dihydrate' _chemical_melting_point ? _chemical_formula_moiety 'C43 H58 N4 O12, 2(C H4 O), 3(H2 O)' _chemical_formula_sum 'C45 H72 N4 O17' _chemical_formula_weight 941.07 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 13.8494(6) _cell_length_b 17.4243(7) _cell_length_c 20.0324(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4834.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 5009 _cell_measurement_theta_min 2.03 _cell_measurement_theta_max 27.75 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.293 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2024 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.964 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ; SCALE3 ABSPACK scaling algorithm (Oxford Diffraction, 2007) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(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 'Kuma KM4CCD \k geometry' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 18270 _diffrn_reflns_av_R_equivalents 0.0418 _diffrn_reflns_av_sigmaI/netI 0.0384 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 4.12 _diffrn_reflns_theta_max 25.35 _reflns_number_total 4875 _reflns_number_gt 4344 _reflns_threshold_expression I>2/s(I) _computing_data_collection ; CrysAlis CCD (Oxford Diffraction, 2007) ; _computing_cell_refinement ; CrysAlis RED ; _computing_data_reduction ; CrysAlis RED (Oxford Diffraction, 2007) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; Ortep III for Windows (Farrugia, 1997), ; _computing_publication_material SHELXL-97 _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^)+(0.0503P)^2^+1.8680P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _chemical_absolute_configuration syn _refine_ls_number_reflns 4875 _refine_ls_number_parameters 613 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0476 _refine_ls_R_factor_gt 0.0400 _refine_ls_wR_factor_ref 0.0996 _refine_ls_wR_factor_gt 0.0948 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.79557(15) 0.25508(12) 0.76757(11) 0.0210(5) Uani 1 1 d . . . H1 H 0.7505 0.2277 0.7526 0.031 Uiso 1 1 calc R . . O4 O 0.65639(14) 0.52049(11) 0.88334(11) 0.0181(5) Uani 1 1 d . . . H4O H 0.5960 0.5242 0.8806 0.027 Uiso 1 1 calc R . . O6 O 0.36113(14) 0.35955(11) 0.81759(10) 0.0168(5) Uani 1 1 d . . . O8 O 0.62685(15) 0.20874(12) 0.75006(11) 0.0220(5) Uani 1 1 d . . . O11 O 0.47259(15) 0.52945(11) 0.87690(11) 0.0195(5) Uani 1 1 d . . . O12 O 0.30213(14) 0.48434(11) 0.79921(10) 0.0173(4) Uani 1 1 d . . . O15 O 0.93733(15) 0.25255(12) 0.86815(11) 0.0220(5) Uani 1 1 d . . . O21 O 0.97071(16) 0.40785(11) 0.57278(11) 0.0219(5) Uani 1 1 d . . . H21O H 0.9215 0.4050 0.5484 0.033 Uiso 1 1 calc R . . O23 O 0.79880(15) 0.45404(11) 0.51930(10) 0.0191(5) Uani 1 1 d . . . H23O H 0.8104 0.4672 0.4798 0.029 Uiso 1 1 calc R . . O25 O 0.60662(15) 0.58894(11) 0.59363(10) 0.0186(5) Uani 1 1 d . . . O27 O 0.41668(15) 0.50116(12) 0.58177(10) 0.0217(5) Uani 1 1 d . . . O35 O 0.5760(2) 0.58255(14) 0.48316(12) 0.0367(6) Uani 1 1 d . . . N2 N 0.92168(17) 0.36490(14) 0.81043(13) 0.0174(5) Uani 1 1 d . . . H2N H 0.9528 0.4096 0.8040 0.026 Uiso 1 1 d R . . N38 N 0.93262(18) 0.51634(13) 0.83818(12) 0.0171(5) Uani 1 1 d . . . N39 N 0.98697(18) 0.58163(13) 0.84958(13) 0.0174(5) Uani 1 1 d . . . N40 N 1.12396(17) 0.68774(13) 0.90290(13) 0.0175(5) Uani 1 1 d . . . H40N H 1.1352 0.6649 0.9424 0.026 Uiso 1 1 d R . . C1 C 0.7582(2) 0.31876(16) 0.79650(15) 0.0169(6) Uani 1 1 d . . . C2 C 0.8208(2) 0.37526(16) 0.81840(15) 0.0149(6) Uani 1 1 d . . . C3 C 0.7851(2) 0.44478(16) 0.84478(14) 0.0149(6) Uani 1 1 d . . . C4 C 0.6861(2) 0.45322(16) 0.85342(14) 0.0154(6) Uani 1 1 d . . . C5 C 0.5165(2) 0.40352(16) 0.83692(14) 0.0142(6) Uani 1 1 d . . . C6 C 0.4581(2) 0.34368(16) 0.81293(14) 0.0148(6) Uani 1 1 d . . . C7 C 0.4901(2) 0.27626(16) 0.78539(15) 0.0155(6) Uani 1 1 d . . . C8 C 0.5917(2) 0.26860(16) 0.77881(14) 0.0160(6) Uani 1 1 d . . . C9 C 0.6573(2) 0.32859(17) 0.80295(15) 0.0155(6) Uani 1 1 d . . . C10 C 0.6207(2) 0.39666(16) 0.83262(15) 0.0149(6) Uani 1 1 d . . . C11 C 0.4554(2) 0.46277(16) 0.85568(15) 0.0155(6) Uani 1 1 d . . . C12 C 0.3513(2) 0.43649(17) 0.84513(15) 0.0174(6) Uani 1 1 d . . . C13 C 0.2914(2) 0.43282(18) 0.90778(16) 0.0211(7) Uani 1 1 d . . . H13A H 0.2908 0.4833 0.9293 0.032 Uiso 1 1 calc R . . H13B H 0.3192 0.3949 0.9384 0.032 Uiso 1 1 calc R . . H13C H 0.2252 0.4178 0.8964 0.032 Uiso 1 1 calc R . . C14 C 0.4230(2) 0.21396(17) 0.76155(16) 0.0212(7) Uani 1 1 d . . . H14A H 0.4278 0.1696 0.7914 0.032 Uiso 1 1 calc R . . H14B H 0.4411 0.1986 0.7162 0.032 Uiso 1 1 calc R . . H14C H 0.3565 0.2332 0.7615 0.032 Uiso 1 1 calc R . . C15 C 0.9727(2) 0.30406(16) 0.83406(15) 0.0174(6) Uani 1 1 d . . . C16 C 1.0788(2) 0.30419(16) 0.81793(16) 0.0189(7) Uani 1 1 d . . . C17 C 1.1178(2) 0.33773(16) 0.76454(16) 0.0202(7) Uani 1 1 d . . . H17 H 1.1859 0.3329 0.7606 0.030 Uiso 1 1 calc R . . C18 C 1.0707(2) 0.38078(16) 0.71135(15) 0.0175(6) Uani 1 1 d . . . H18 H 1.0057 0.3686 0.7004 0.026 Uiso 1 1 calc R . . C19 C 1.1146(2) 0.43619(18) 0.67753(15) 0.0203(7) Uani 1 1 d . . . H19 H 1.1829 0.4386 0.6815 0.031 Uiso 1 1 calc R . . C20 C 1.0682(2) 0.49527(17) 0.63386(15) 0.0183(6) Uani 1 1 d . . . H20 H 1.1074 0.4998 0.5921 0.027 Uiso 1 1 calc R . . C21 C 0.9645(2) 0.47551(16) 0.61400(16) 0.0182(6) Uani 1 1 d . . . H21 H 0.9281 0.4618 0.6555 0.027 Uiso 1 1 calc R . . C22 C 0.9101(2) 0.54047(17) 0.57901(15) 0.0177(6) Uani 1 1 d . . . H22 H 0.9080 0.5843 0.6112 0.027 Uiso 1 1 calc R . . C23 C 0.8042(2) 0.52040(17) 0.56226(15) 0.0175(6) Uani 1 1 d . . . H23 H 0.7761 0.5648 0.5374 0.026 Uiso 1 1 calc R . . C24 C 0.7368(2) 0.50268(18) 0.62117(15) 0.0181(6) Uani 1 1 d . . . H24 H 0.7495 0.4486 0.6354 0.027 Uiso 1 1 calc R . . C25 C 0.6307(2) 0.50715(16) 0.59736(15) 0.0178(6) Uani 1 1 d . . . H25 H 0.6259 0.4844 0.5517 0.027 Uiso 1 1 calc R . . C26 C 0.5591(2) 0.46565(16) 0.64385(15) 0.0178(6) Uani 1 1 d . . . H26 H 0.5868 0.4675 0.6899 0.027 Uiso 1 1 calc R . . C27 C 0.4598(2) 0.50420(17) 0.64676(15) 0.0170(6) Uani 1 1 d . . . H27 H 0.4698 0.5594 0.6585 0.025 Uiso 1 1 calc R . . C28 C 0.3952(2) 0.46962(16) 0.69879(15) 0.0162(6) Uani 1 1 d . . . H28 H 0.3813 0.4163 0.6973 0.024 Uiso 1 1 calc R . . C29 C 0.3576(2) 0.51205(16) 0.74643(15) 0.0163(6) Uani 1 1 d . . . H29 H 0.3691 0.5658 0.7447 0.024 Uiso 1 1 calc R . . C30 C 1.1388(2) 0.26301(19) 0.86931(19) 0.0299(8) Uani 1 1 d . . . H30A H 1.2069 0.2649 0.8562 0.045 Uiso 1 1 calc R . . H30B H 1.1178 0.2094 0.8723 0.045 Uiso 1 1 calc R . . H30C H 1.1307 0.2879 0.9128 0.045 Uiso 1 1 calc R . . C32 C 0.9627(2) 0.56955(18) 0.51680(16) 0.0224(7) Uani 1 1 d . . . H32A H 1.0208 0.5977 0.5302 0.034 Uiso 1 1 calc R . . H32B H 0.9200 0.6037 0.4916 0.034 Uiso 1 1 calc R . . H32C H 0.9811 0.5258 0.4887 0.034 Uiso 1 1 calc R . . C33 C 0.7538(2) 0.55441(19) 0.68196(16) 0.0229(7) Uani 1 1 d . . . H33A H 0.8159 0.5416 0.7025 0.034 Uiso 1 1 calc R . . H33B H 0.7018 0.5465 0.7145 0.034 Uiso 1 1 calc R . . H33C H 0.7543 0.6082 0.6678 0.034 Uiso 1 1 calc R . . C31 C 1.0741(3) 0.57236(18) 0.67148(17) 0.0244(7) Uani 1 1 d . . . H31A H 1.0310 0.5709 0.7103 0.037 Uiso 1 1 calc R . . H31B H 1.0544 0.6141 0.6416 0.037 Uiso 1 1 calc R . . H31C H 1.1405 0.5810 0.6864 0.037 Uiso 1 1 calc R . . C34 C 0.5545(2) 0.38113(17) 0.62323(18) 0.0260(7) Uani 1 1 d . . . H34A H 0.5168 0.3523 0.6561 0.039 Uiso 1 1 calc R . . H34B H 0.6201 0.3601 0.6211 0.039 Uiso 1 1 calc R . . H34C H 0.5239 0.3768 0.5793 0.039 Uiso 1 1 calc R . . C35 C 0.5785(2) 0.61838(19) 0.53416(16) 0.0229(7) Uani 1 1 d . . . C36 C 0.5515(3) 0.70131(19) 0.54189(18) 0.0305(8) Uani 1 1 d . . . H36A H 0.5357 0.7229 0.4981 0.046 Uiso 1 1 calc R . . H36B H 0.6059 0.7296 0.5613 0.046 Uiso 1 1 calc R . . H36C H 0.4953 0.7056 0.5714 0.046 Uiso 1 1 calc R . . C37 C 0.3443(2) 0.5594(2) 0.57292(19) 0.0318(8) Uani 1 1 d . . . H37A H 0.2887 0.5480 0.6016 0.048 Uiso 1 1 calc R . . H37B H 0.3236 0.5603 0.5261 0.048 Uiso 1 1 calc R . . H37C H 0.3712 0.6095 0.5850 0.048 Uiso 1 1 calc R . . C38 C 0.8469(2) 0.51032(16) 0.86175(15) 0.0169(6) Uani 1 1 d . . . H38 H 0.8230 0.5490 0.8908 0.025 Uiso 1 1 calc R . . C39 C 0.9569(2) 0.63560(17) 0.90023(17) 0.0230(7) Uani 1 1 d . . . H39A H 0.9629 0.6117 0.9449 0.035 Uiso 1 1 calc R . . H39B H 0.8884 0.6497 0.8932 0.035 Uiso 1 1 calc R . . C40 C 1.0195(2) 0.70712(17) 0.89692(19) 0.0241(7) Uani 1 1 d . . . H40A H 1.0081 0.7338 0.8540 0.036 Uiso 1 1 calc R . . H40B H 1.0011 0.7425 0.9334 0.036 Uiso 1 1 calc R . . C41 C 1.1513(2) 0.63066(17) 0.85061(16) 0.0197(7) Uani 1 1 d . . . H41A H 1.2199 0.6160 0.8561 0.030 Uiso 1 1 calc R . . H41B H 1.1434 0.6538 0.8058 0.030 Uiso 1 1 calc R . . C42 C 1.0882(2) 0.56000(17) 0.85623(16) 0.0188(6) Uani 1 1 d . . . H42A H 1.1057 0.5229 0.8208 0.028 Uiso 1 1 calc R . . H42B H 1.0989 0.5350 0.9000 0.028 Uiso 1 1 calc R . . C43 C 1.1856(2) 0.75781(17) 0.89961(17) 0.0240(7) Uani 1 1 d . . . H43A H 1.1736 0.7848 0.8575 0.036 Uiso 1 1 calc R . . H43B H 1.2538 0.7430 0.9021 0.036 Uiso 1 1 calc R . . H43C H 1.1700 0.7917 0.9371 0.036 Uiso 1 1 calc R . . O1A O 0.7829(2) 0.20364(17) 0.94438(16) 0.0522(8) Uani 1 1 d . . . H1OA H 0.8223 0.2149 0.9141 0.078 Uiso 1 1 calc R . . C1A C 0.7298(3) 0.2684(3) 0.9616(2) 0.0462(11) Uani 1 1 d . . . H1A1 H 0.7321 0.2756 1.0101 0.069 Uiso 1 1 calc R . . H1A2 H 0.6626 0.2617 0.9474 0.069 Uiso 1 1 calc R . . H1A3 H 0.7573 0.3135 0.9395 0.069 Uiso 1 1 calc R . . O1B O 0.5860(2) 0.7124(2) 0.95606(14) 0.0485(7) Uani 1 1 d . . . H1OB H 0.5384 0.7010 0.9321 0.073 Uiso 1 1 calc R . . C1B C 0.6709(3) 0.7185(3) 0.9151(3) 0.0606(13) Uani 1 1 d . . . H1B1 H 0.6662 0.7644 0.8870 0.091 Uiso 1 1 calc R . . H1B2 H 0.6763 0.6729 0.8867 0.091 Uiso 1 1 calc R . . H1B3 H 0.7281 0.7224 0.9437 0.091 Uiso 1 1 calc R . . O1C O 0.3169(2) 0.39108(18) 0.50953(16) 0.0598(9) Uani 1 1 d . . . H1OC H 0.3438 0.4205 0.5371 0.090 Uiso 1 1 d R . . H2OC H 0.2684 0.3735 0.5295 0.090 Uiso 1 1 d R . . O1D O 0.41301(17) 0.67549(12) 0.88365(11) 0.0250(5) Uani 1 1 d . . . H1OD H 0.3993 0.6939 0.8460 0.037 Uiso 1 1 d R . . H2OD H 0.4311 0.6302 0.8760 0.037 Uiso 1 1 d R . . O1E O 1.13614(16) 0.33677(14) 0.52337(12) 0.0328(6) Uani 1 1 d . . . H2OE H 1.1225 0.3312 0.4829 0.049 Uiso 1 1 d R . . H1OE H 1.0882 0.3588 0.5404 0.049 Uiso 1 1 d 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 O1 0.0171(11) 0.0177(10) 0.0282(12) -0.0100(9) -0.0010(10) 0.0015(9) O4 0.0125(10) 0.0164(10) 0.0255(11) -0.0060(9) 0.0009(9) 0.0008(8) O6 0.0116(10) 0.0162(10) 0.0225(11) -0.0020(9) -0.0007(9) 0.0002(8) O8 0.0188(11) 0.0178(10) 0.0294(12) -0.0077(9) -0.0024(10) 0.0016(9) O11 0.0178(10) 0.0171(10) 0.0235(11) -0.0031(9) -0.0021(10) 0.0022(9) O12 0.0122(10) 0.0232(10) 0.0165(10) 0.0028(9) 0.0012(9) 0.0023(9) O15 0.0181(11) 0.0179(10) 0.0301(13) 0.0030(9) 0.0023(10) -0.0010(9) O21 0.0183(11) 0.0182(10) 0.0292(13) -0.0078(9) -0.0053(10) 0.0025(9) O23 0.0196(11) 0.0225(11) 0.0153(10) -0.0020(9) 0.0038(9) -0.0006(9) O25 0.0175(10) 0.0186(10) 0.0197(11) 0.0033(9) 0.0014(9) 0.0021(9) O27 0.0196(11) 0.0279(11) 0.0174(11) 0.0024(9) -0.0016(9) 0.0012(10) O35 0.0575(17) 0.0342(13) 0.0184(12) 0.0032(11) -0.0005(13) 0.0112(13) N2 0.0118(12) 0.0146(11) 0.0260(14) 0.0031(11) -0.0004(11) -0.0007(10) N38 0.0153(12) 0.0135(11) 0.0225(13) 0.0016(10) -0.0014(11) -0.0019(10) N39 0.0152(12) 0.0124(11) 0.0247(14) -0.0026(11) 0.0008(11) -0.0014(10) N40 0.0161(13) 0.0163(11) 0.0202(13) -0.0003(11) 0.0014(11) -0.0035(11) C1 0.0177(15) 0.0173(14) 0.0158(15) -0.0012(13) 0.0019(13) 0.0029(13) C2 0.0130(13) 0.0159(14) 0.0157(14) 0.0020(12) 0.0010(12) 0.0015(12) C3 0.0173(14) 0.0148(13) 0.0126(14) 0.0013(12) -0.0031(12) -0.0019(12) C4 0.0183(14) 0.0135(13) 0.0146(14) 0.0004(12) 0.0023(13) 0.0029(12) C5 0.0153(14) 0.0155(14) 0.0119(14) 0.0018(12) -0.0011(12) 0.0000(12) C6 0.0142(14) 0.0181(14) 0.0122(14) 0.0043(12) 0.0016(12) -0.0001(12) C7 0.0170(15) 0.0141(13) 0.0153(15) -0.0013(12) 0.0008(13) -0.0007(12) C8 0.0181(15) 0.0151(14) 0.0149(15) -0.0005(12) -0.0010(13) 0.0001(12) C9 0.0148(14) 0.0169(14) 0.0147(14) 0.0019(12) -0.0016(12) 0.0019(12) C10 0.0151(14) 0.0156(14) 0.0141(14) 0.0015(12) -0.0004(12) 0.0003(12) C11 0.0154(14) 0.0187(14) 0.0124(14) -0.0008(12) -0.0003(12) -0.0003(12) C12 0.0182(15) 0.0171(14) 0.0169(15) -0.0013(12) -0.0014(13) 0.0017(13) C13 0.0190(15) 0.0225(15) 0.0218(16) 0.0027(13) 0.0013(14) 0.0009(13) C14 0.0182(15) 0.0188(14) 0.0264(17) -0.0026(13) -0.0012(14) -0.0006(13) C15 0.0172(15) 0.0138(14) 0.0212(16) -0.0035(13) -0.0016(13) -0.0013(12) C16 0.0136(14) 0.0139(14) 0.0294(17) -0.0005(13) -0.0018(14) 0.0014(12) C17 0.0122(14) 0.0188(15) 0.0295(17) -0.0026(14) 0.0015(14) 0.0007(12) C18 0.0131(14) 0.0175(14) 0.0219(15) -0.0034(12) 0.0008(13) 0.0006(13) C19 0.0133(14) 0.0264(16) 0.0214(16) -0.0030(14) 0.0014(13) -0.0011(13) C20 0.0161(15) 0.0198(14) 0.0190(15) 0.0006(13) 0.0038(13) 0.0002(13) C21 0.0174(15) 0.0165(14) 0.0208(15) -0.0019(13) 0.0023(13) 0.0005(12) C22 0.0171(15) 0.0176(14) 0.0183(15) 0.0000(12) 0.0030(13) 0.0007(12) C23 0.0181(15) 0.0168(14) 0.0177(15) 0.0009(12) 0.0026(13) 0.0038(13) C24 0.0151(15) 0.0226(14) 0.0167(15) 0.0027(13) 0.0016(13) 0.0034(13) C25 0.0174(15) 0.0162(14) 0.0200(15) 0.0012(13) 0.0010(13) 0.0035(12) C26 0.0178(15) 0.0196(14) 0.0160(14) 0.0026(12) 0.0031(13) 0.0034(12) C27 0.0150(14) 0.0199(14) 0.0160(15) -0.0001(12) -0.0022(12) 0.0005(12) C28 0.0129(14) 0.0166(14) 0.0191(15) 0.0016(12) -0.0037(13) -0.0008(12) C29 0.0123(13) 0.0181(14) 0.0185(15) 0.0030(12) -0.0012(13) 0.0001(12) C30 0.0164(16) 0.0276(17) 0.046(2) 0.0152(16) -0.0017(16) 0.0013(14) C32 0.0202(16) 0.0245(16) 0.0224(16) 0.0033(14) 0.0046(14) 0.0006(14) C33 0.0179(15) 0.0307(17) 0.0200(16) 0.0015(14) 0.0030(14) 0.0047(14) C31 0.0260(17) 0.0204(15) 0.0268(17) -0.0027(13) -0.0016(15) -0.0020(14) C34 0.0271(17) 0.0205(15) 0.0303(18) 0.0038(14) 0.0087(15) 0.0041(14) C35 0.0225(16) 0.0276(16) 0.0187(16) 0.0071(14) 0.0029(14) 0.0057(14) C36 0.036(2) 0.0261(17) 0.0292(18) 0.0082(15) 0.0067(16) 0.0098(16) C37 0.0225(17) 0.0371(19) 0.036(2) 0.0097(17) -0.0092(16) 0.0049(16) C38 0.0170(15) 0.0128(13) 0.0209(15) -0.0005(12) -0.0011(13) 0.0008(12) C39 0.0163(15) 0.0200(14) 0.0327(19) -0.0104(14) 0.0022(14) -0.0027(13) C40 0.0145(15) 0.0170(14) 0.041(2) -0.0050(15) 0.0021(15) 0.0017(13) C41 0.0163(14) 0.0180(14) 0.0247(16) -0.0037(13) 0.0056(14) -0.0014(13) C42 0.0143(14) 0.0144(13) 0.0278(17) -0.0010(13) 0.0019(14) 0.0009(12) C43 0.0226(16) 0.0202(15) 0.0292(18) -0.0005(14) 0.0030(15) -0.0057(14) O1A 0.0533(18) 0.0462(16) 0.057(2) -0.0011(15) 0.0225(16) -0.0198(15) C1A 0.033(2) 0.065(3) 0.040(2) 0.010(2) 0.0053(19) -0.005(2) O1B 0.0316(14) 0.078(2) 0.0357(15) 0.0023(15) -0.0031(13) -0.0103(15) C1B 0.053(3) 0.070(3) 0.059(3) -0.005(3) -0.003(3) -0.007(3) O1C 0.0435(16) 0.077(2) 0.0588(19) -0.0428(18) 0.0241(15) -0.0290(16) O1D 0.0323(13) 0.0192(10) 0.0234(11) 0.0019(9) 0.0007(11) 0.0068(10) O1E 0.0228(12) 0.0460(15) 0.0296(13) -0.0080(12) 0.0004(11) 0.0068(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.355(4) . ? O1 H1 0.8400 . ? O4 C4 1.379(3) . ? O4 H4O 0.8400 . ? O6 C6 1.375(3) . ? O6 C12 1.456(3) . ? O8 C8 1.287(4) . ? O11 C11 1.260(3) . ? O12 C29 1.393(4) . ? O12 C12 1.416(4) . ? O15 C15 1.230(4) . ? O21 C21 1.442(3) . ? O21 H21O 0.8400 . ? O23 C23 1.443(4) . ? O23 H23O 0.8400 . ? O25 C35 1.354(4) . ? O25 C25 1.465(3) . ? O27 C27 1.433(4) . ? O27 C37 1.437(4) . ? O35 C35 1.198(4) . ? N2 C15 1.359(4) . ? N2 C2 1.417(4) . ? N2 H2N 0.9000 . ? N38 C38 1.281(4) . ? N38 N39 1.383(3) . ? N39 C39 1.444(4) . ? N39 C42 1.458(4) . ? N40 C40 1.490(4) . ? N40 C43 1.491(4) . ? N40 C41 1.493(4) . ? N40 H40N 0.9001 . ? C1 C2 1.383(4) . ? C1 C9 1.413(4) . ? C2 C3 1.411(4) . ? C3 C4 1.390(4) . ? C3 C38 1.467(4) . ? C4 C10 1.402(4) . ? C5 C11 1.387(4) . ? C5 C6 1.404(4) . ? C5 C10 1.451(4) . ? C6 C7 1.371(4) . ? C7 C8 1.420(4) . ? C7 C14 1.506(4) . ? C8 C9 1.467(4) . ? C9 C10 1.420(4) . ? C11 C12 1.527(4) . ? C12 C13 1.506(4) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C16 1.505(4) . ? C16 C17 1.333(5) . ? C16 C30 1.505(4) . ? C17 C18 1.457(4) . ? C17 H17 0.9500 . ? C18 C19 1.327(4) . ? C18 H18 0.9500 . ? C19 C20 1.496(4) . ? C19 H19 0.9500 . ? C20 C21 1.530(4) . ? C20 C31 1.542(4) . ? C20 H20 1.0000 . ? C21 C22 1.529(4) . ? C21 H21 1.0000 . ? C22 C32 1.530(4) . ? C22 C23 1.545(4) . ? C22 H22 1.0000 . ? C23 C24 1.536(4) . ? C23 H23 1.0000 . ? C24 C33 1.533(4) . ? C24 C25 1.548(4) . ? C24 H24 1.0000 . ? C25 C26 1.540(4) . ? C25 H25 1.0000 . ? C26 C34 1.531(4) . ? C26 C27 1.532(4) . ? C26 H26 1.0000 . ? C27 C28 1.500(4) . ? C27 H27 1.0000 . ? C28 C29 1.315(4) . ? C28 H28 0.9500 . ? C29 H29 0.9500 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? C35 C36 1.501(4) . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? C38 H38 0.9500 . ? C39 C40 1.520(4) . ? C39 H39A 0.9900 . ? C39 H39B 0.9900 . ? C40 H40A 0.9900 . ? C40 H40B 0.9900 . ? C41 C42 1.513(4) . ? C41 H41A 0.9900 . ? C41 H41B 0.9900 . ? C42 H42A 0.9900 . ? C42 H42B 0.9900 . ? C43 H43A 0.9800 . ? C43 H43B 0.9800 . ? C43 H43C 0.9800 . ? O1A C1A 1.391(5) . ? O1A H1OA 0.8400 . ? C1A H1A1 0.9800 . ? C1A H1A2 0.9800 . ? C1A H1A3 0.9800 . ? O1B C1B 1.438(5) . ? O1B H1OB 0.8400 . ? C1B H1B1 0.9800 . ? C1B H1B2 0.9800 . ? C1B H1B3 0.9800 . ? O1C H1OC 0.8401 . ? O1C H2OC 0.8399 . ? O1D H1OD 0.8408 . ? O1D H2OD 0.8421 . ? O1E H2OE 0.8388 . ? O1E H1OE 0.8396 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 H1 109.5 . . ? C4 O4 H4O 109.5 . . ? C6 O6 C12 107.6(2) . . ? C29 O12 C12 115.6(2) . . ? C21 O21 H21O 109.5 . . ? C23 O23 H23O 109.5 . . ? C35 O25 C25 118.6(2) . . ? C27 O27 C37 112.1(2) . . ? C15 N2 C2 124.9(3) . . ? C15 N2 H2N 118.5 . . ? C2 N2 H2N 112.2 . . ? C38 N38 N39 120.7(2) . . ? N38 N39 C39 119.7(2) . . ? N38 N39 C42 109.0(2) . . ? C39 N39 C42 112.4(2) . . ? C40 N40 C43 111.5(2) . . ? C40 N40 C41 109.9(2) . . ? C43 N40 C41 111.7(2) . . ? C40 N40 H40N 109.8 . . ? C43 N40 H40N 107.6 . . ? C41 N40 H40N 106.2 . . ? O1 C1 C2 118.6(3) . . ? O1 C1 C9 121.1(3) . . ? C2 C1 C9 120.3(3) . . ? C1 C2 C3 120.7(3) . . ? C1 C2 N2 119.4(3) . . ? C3 C2 N2 119.8(3) . . ? C4 C3 C2 118.9(3) . . ? C4 C3 C38 117.7(3) . . ? C2 C3 C38 123.4(3) . . ? O4 C4 C3 116.0(3) . . ? O4 C4 C10 122.3(3) . . ? C3 C4 C10 121.7(3) . . ? C11 C5 C6 107.1(3) . . ? C11 C5 C10 133.2(3) . . ? C6 C5 C10 119.4(3) . . ? C7 C6 O6 121.0(3) . . ? C7 C6 C5 126.1(3) . . ? O6 C6 C5 112.9(2) . . ? C6 C7 C8 115.9(3) . . ? C6 C7 C14 123.1(3) . . ? C8 C7 C14 120.9(3) . . ? O8 C8 C7 119.5(3) . . ? O8 C8 C9 119.3(3) . . ? C7 C8 C9 121.1(3) . . ? C1 C9 C10 119.5(3) . . ? C1 C9 C8 119.7(3) . . ? C10 C9 C8 120.7(3) . . ? C4 C10 C9 118.7(3) . . ? C4 C10 C5 124.6(3) . . ? C9 C10 C5 116.7(3) . . ? O11 C11 C5 131.5(3) . . ? O11 C11 C12 120.1(3) . . ? C5 C11 C12 108.4(2) . . ? O12 C12 O6 109.9(2) . . ? O12 C12 C13 107.6(2) . . ? O6 C12 C13 109.2(2) . . ? O12 C12 C11 111.5(2) . . ? O6 C12 C11 103.9(2) . . ? C13 C12 C11 114.7(2) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C7 C14 H14A 109.5 . . ? C7 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C7 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O15 C15 N2 123.8(3) . . ? O15 C15 C16 120.6(3) . . ? N2 C15 C16 115.6(3) . . ? C17 C16 C15 124.7(3) . . ? C17 C16 C30 122.3(3) . . ? C15 C16 C30 113.1(3) . . ? C16 C17 C18 129.1(3) . . ? C16 C17 H17 115.4 . . ? C18 C17 H17 115.4 . . ? C19 C18 C17 122.9(3) . . ? C19 C18 H18 118.5 . . ? C17 C18 H18 118.5 . . ? C18 C19 C20 127.1(3) . . ? C18 C19 H19 116.5 . . ? C20 C19 H19 116.5 . . ? C19 C20 C21 113.6(2) . . ? C19 C20 C31 106.9(3) . . ? C21 C20 C31 111.9(2) . . ? C19 C20 H20 108.1 . . ? C21 C20 H20 108.1 . . ? C31 C20 H20 108.1 . . ? O21 C21 C22 111.9(2) . . ? O21 C21 C20 106.0(2) . . ? C22 C21 C20 114.5(2) . . ? O21 C21 H21 108.1 . . ? C22 C21 H21 108.1 . . ? C20 C21 H21 108.1 . . ? C21 C22 C32 112.6(2) . . ? C21 C22 C23 113.5(2) . . ? C32 C22 C23 110.5(3) . . ? C21 C22 H22 106.6 . . ? C32 C22 H22 106.6 . . ? C23 C22 H22 106.6 . . ? O23 C23 C24 105.4(2) . . ? O23 C23 C22 111.1(2) . . ? C24 C23 C22 117.1(3) . . ? O23 C23 H23 107.6 . . ? C24 C23 H23 107.6 . . ? C22 C23 H23 107.6 . . ? C33 C24 C23 113.5(3) . . ? C33 C24 C25 111.1(2) . . ? C23 C24 C25 109.3(2) . . ? C33 C24 H24 107.6 . . ? C23 C24 H24 107.6 . . ? C25 C24 H24 107.6 . . ? O25 C25 C26 109.9(2) . . ? O25 C25 C24 106.3(2) . . ? C26 C25 C24 113.7(2) . . ? O25 C25 H25 108.9 . . ? C26 C25 H25 108.9 . . ? C24 C25 H25 108.9 . . ? C34 C26 C27 113.3(3) . . ? C34 C26 C25 108.3(2) . . ? C27 C26 C25 113.3(2) . . ? C34 C26 H26 107.2 . . ? C27 C26 H26 107.2 . . ? C25 C26 H26 107.2 . . ? O27 C27 C28 111.6(2) . . ? O27 C27 C26 108.9(2) . . ? C28 C27 C26 112.7(2) . . ? O27 C27 H27 107.8 . . ? C28 C27 H27 107.8 . . ? C26 C27 H27 107.8 . . ? C29 C28 C27 121.0(3) . . ? C29 C28 H28 119.5 . . ? C27 C28 H28 119.5 . . ? C28 C29 O12 125.1(3) . . ? C28 C29 H29 117.5 . . ? O12 C29 H29 117.5 . . ? C16 C30 H30A 109.5 . . ? C16 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C16 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C22 C32 H32A 109.5 . . ? C22 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C22 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C24 C33 H33A 109.5 . . ? C24 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C24 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C20 C31 H31A 109.5 . . ? C20 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C20 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C26 C34 H34A 109.5 . . ? C26 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C26 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? O35 C35 O25 124.1(3) . . ? O35 C35 C36 125.7(3) . . ? O25 C35 C36 110.2(3) . . ? 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 . . ? O27 C37 H37A 109.5 . . ? O27 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? O27 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? N38 C38 C3 121.2(3) . . ? N38 C38 H38 119.4 . . ? C3 C38 H38 119.4 . . ? N39 C39 C40 109.8(3) . . ? N39 C39 H39A 109.7 . . ? C40 C39 H39A 109.7 . . ? N39 C39 H39B 109.7 . . ? C40 C39 H39B 109.7 . . ? H39A C39 H39B 108.2 . . ? N40 C40 C39 111.4(2) . . ? N40 C40 H40A 109.4 . . ? C39 C40 H40A 109.4 . . ? N40 C40 H40B 109.4 . . ? C39 C40 H40B 109.4 . . ? H40A C40 H40B 108.0 . . ? N40 C41 C42 110.1(2) . . ? N40 C41 H41A 109.6 . . ? C42 C41 H41A 109.6 . . ? N40 C41 H41B 109.6 . . ? C42 C41 H41B 109.6 . . ? H41A C41 H41B 108.2 . . ? N39 C42 C41 109.7(2) . . ? N39 C42 H42A 109.7 . . ? C41 C42 H42A 109.7 . . ? N39 C42 H42B 109.7 . . ? C41 C42 H42B 109.7 . . ? H42A C42 H42B 108.2 . . ? N40 C43 H43A 109.5 . . ? N40 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? N40 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? C1A O1A H1OA 109.5 . . ? 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 . . ? C1B O1B H1OB 109.5 . . ? O1B C1B H1B1 109.5 . . ? O1B C1B H1B2 109.5 . . ? H1B1 C1B H1B2 109.5 . . ? O1B C1B H1B3 109.5 . . ? H1B1 C1B H1B3 109.5 . . ? H1B2 C1B H1B3 109.5 . . ? H1OC O1C H2OC 105.4 . . ? H1OD O1D H2OD 105.1 . . ? H2OE O1E H1OE 105.5 . . ? 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 C38 N38 N39 C39 14.2(4) . . . . ? C38 N38 N39 C42 145.4(3) . . . . ? O1 C1 C2 C3 175.8(3) . . . . ? C9 C1 C2 C3 -2.8(4) . . . . ? O1 C1 C2 N2 -0.4(4) . . . . ? C9 C1 C2 N2 -178.9(3) . . . . ? C15 N2 C2 C1 -55.9(4) . . . . ? C15 N2 C2 C3 127.9(3) . . . . ? C1 C2 C3 C4 5.1(4) . . . . ? N2 C2 C3 C4 -178.7(3) . . . . ? C1 C2 C3 C38 -172.8(3) . . . . ? N2 C2 C3 C38 3.4(4) . . . . ? C2 C3 C4 O4 176.0(3) . . . . ? C38 C3 C4 O4 -6.0(4) . . . . ? C2 C3 C4 C10 -4.2(4) . . . . ? C38 C3 C4 C10 173.8(3) . . . . ? C12 O6 C6 C7 -176.7(3) . . . . ? C12 O6 C6 C5 1.5(3) . . . . ? C11 C5 C6 C7 175.6(3) . . . . ? C10 C5 C6 C7 0.8(4) . . . . ? C11 C5 C6 O6 -2.5(3) . . . . ? C10 C5 C6 O6 -177.3(3) . . . . ? O6 C6 C7 C8 175.6(3) . . . . ? C5 C6 C7 C8 -2.4(4) . . . . ? O6 C6 C7 C14 -2.9(4) . . . . ? C5 C6 C7 C14 179.1(3) . . . . ? C6 C7 C8 O8 -176.2(3) . . . . ? C14 C7 C8 O8 2.3(4) . . . . ? C6 C7 C8 C9 2.4(4) . . . . ? C14 C7 C8 C9 -179.0(3) . . . . ? O1 C1 C9 C10 -179.0(3) . . . . ? C2 C1 C9 C10 -0.5(4) . . . . ? O1 C1 C9 C8 0.8(4) . . . . ? C2 C1 C9 C8 179.3(3) . . . . ? O8 C8 C9 C1 -2.2(4) . . . . ? C7 C8 C9 C1 179.1(3) . . . . ? O8 C8 C9 C10 177.6(3) . . . . ? C7 C8 C9 C10 -1.0(4) . . . . ? O4 C4 C10 C9 -179.2(3) . . . . ? C3 C4 C10 C9 1.0(4) . . . . ? O4 C4 C10 C5 3.1(5) . . . . ? C3 C4 C10 C5 -176.6(3) . . . . ? C1 C9 C10 C4 1.4(4) . . . . ? C8 C9 C10 C4 -178.4(3) . . . . ? C1 C9 C10 C5 179.2(3) . . . . ? C8 C9 C10 C5 -0.6(4) . . . . ? C11 C5 C10 C4 5.3(5) . . . . ? C6 C5 C10 C4 178.5(3) . . . . ? C11 C5 C10 C9 -172.4(3) . . . . ? C6 C5 C10 C9 0.8(4) . . . . ? C6 C5 C11 O11 -176.1(3) . . . . ? C10 C5 C11 O11 -2.3(6) . . . . ? C6 C5 C11 C12 2.4(3) . . . . ? C10 C5 C11 C12 176.2(3) . . . . ? C29 O12 C12 O6 -78.6(3) . . . . ? C29 O12 C12 C13 162.6(2) . . . . ? C29 O12 C12 C11 36.1(3) . . . . ? C6 O6 C12 O12 119.5(2) . . . . ? C6 O6 C12 C13 -122.7(2) . . . . ? C6 O6 C12 C11 0.0(3) . . . . ? O11 C11 C12 O12 58.8(4) . . . . ? C5 C11 C12 O12 -119.9(3) . . . . ? O11 C11 C12 O6 177.1(2) . . . . ? C5 C11 C12 O6 -1.5(3) . . . . ? O11 C11 C12 C13 -63.8(4) . . . . ? C5 C11 C12 C13 117.6(3) . . . . ? C2 N2 C15 O15 -3.7(5) . . . . ? C2 N2 C15 C16 178.4(3) . . . . ? O15 C15 C16 C17 154.2(3) . . . . ? N2 C15 C16 C17 -27.8(4) . . . . ? O15 C15 C16 C30 -26.7(4) . . . . ? N2 C15 C16 C30 151.3(3) . . . . ? C15 C16 C17 C18 0.4(5) . . . . ? C30 C16 C17 C18 -178.6(3) . . . . ? C16 C17 C18 C19 151.3(3) . . . . ? C17 C18 C19 C20 -164.9(3) . . . . ? C18 C19 C20 C21 -16.1(4) . . . . ? C18 C19 C20 C31 107.8(4) . . . . ? C19 C20 C21 O21 -65.6(3) . . . . ? C31 C20 C21 O21 173.3(2) . . . . ? C19 C20 C21 C22 170.6(3) . . . . ? C31 C20 C21 C22 49.4(4) . . . . ? O21 C21 C22 C32 -64.6(3) . . . . ? C20 C21 C22 C32 56.1(3) . . . . ? O21 C21 C22 C23 61.9(3) . . . . ? C20 C21 C22 C23 -177.4(2) . . . . ? C21 C22 C23 O23 -59.2(3) . . . . ? C32 C22 C23 O23 68.4(3) . . . . ? C21 C22 C23 C24 61.9(3) . . . . ? C32 C22 C23 C24 -170.5(2) . . . . ? O23 C23 C24 C33 163.3(2) . . . . ? C22 C23 C24 C33 39.2(4) . . . . ? O23 C23 C24 C25 -72.0(3) . . . . ? C22 C23 C24 C25 163.9(2) . . . . ? C35 O25 C25 C26 -115.9(3) . . . . ? C35 O25 C25 C24 120.6(3) . . . . ? C33 C24 C25 O25 48.1(3) . . . . ? C23 C24 C25 O25 -77.9(3) . . . . ? C33 C24 C25 C26 -72.9(3) . . . . ? C23 C24 C25 C26 161.0(2) . . . . ? O25 C25 C26 C34 154.5(2) . . . . ? C24 C25 C26 C34 -86.5(3) . . . . ? O25 C25 C26 C27 27.9(3) . . . . ? C24 C25 C26 C27 146.9(3) . . . . ? C37 O27 C27 C28 77.6(3) . . . . ? C37 O27 C27 C26 -157.4(2) . . . . ? C34 C26 C27 O27 -60.7(3) . . . . ? C25 C26 C27 O27 63.2(3) . . . . ? C34 C26 C27 C28 63.7(3) . . . . ? C25 C26 C27 C28 -172.4(2) . . . . ? O27 C27 C28 C29 -114.1(3) . . . . ? C26 C27 C28 C29 123.1(3) . . . . ? C27 C28 C29 O12 -175.6(2) . . . . ? C12 O12 C29 C28 66.2(4) . . . . ? C25 O25 C35 O35 -3.5(5) . . . . ? C25 O25 C35 C36 176.5(3) . . . . ? N39 N38 C38 C3 174.1(3) . . . . ? C4 C3 C38 N38 -159.7(3) . . . . ? C2 C3 C38 N38 18.3(5) . . . . ? N38 N39 C39 C40 -172.3(3) . . . . ? C42 N39 C39 C40 57.9(3) . . . . ? C43 N40 C40 C39 180.0(3) . . . . ? C41 N40 C40 C39 55.6(3) . . . . ? N39 C39 C40 N40 -55.7(4) . . . . ? C40 N40 C41 C42 -56.6(3) . . . . ? C43 N40 C41 C42 179.1(2) . . . . ? N38 N39 C42 C41 165.3(2) . . . . ? C39 N39 C42 C41 -59.6(3) . . . . ? N40 C41 C42 N39 58.1(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 O8 0.84 1.75 2.497(3) 148 . O21 H21O O23 0.84 1.99 2.732(3) 147 . O4 H4O O11 0.84 1.71 2.553(3) 178 . N2 H2N N38 0.90 2.00 2.701(3) 134 . O1A H1OA O15 0.84 1.95 2.763(3) 162 . O1D H2OD O11 0.84 1.85 2.678(3) 169 . O1E H1OE O21 0.84 1.95 2.786(3) 175 . O1C H2OC O1E 0.84 1.94 2.691(4) 147 1_455 O23 H23O O4 0.84 2.00 2.828(3) 170 2_664 O1B H1OB O1D 0.84 2.04 2.874(4) 173 . O1D H1OD O8 0.84 1.98 2.796(3) 165 3_656 O1E H2OE O1D 0.84 2.05 2.888(3) 176 2_664 O1C H1OC O27 0.84 1.95 2.772(4) 166 . N40 H40N O1C 0.90 1.79 2.668(4) 165 2_665 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.621 _refine_diff_density_min -0.476 _refine_diff_density_rms 0.046 # Attachment '- CH2Cl2_3CH3OH.cif' data_b75 _database_code_depnum_ccdc_archive 'CCDC 859794' #TrackingRef '- CH2Cl2_3CH3OH.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(C41 H54 N2 O12), 3(C H4 O), (C H2 Cl2)' _chemical_formula_sum 'C45 H68 Cl2 N2 O15' _chemical_formula_weight 947.91 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.2035(1) _cell_length_b 20.0206(1) _cell_length_c 13.8049(1) _cell_angle_alpha 90.00 _cell_angle_beta 103.152(1) _cell_angle_gamma 90.00 _cell_volume 2476.96(3) _cell_formula_units_Z 2 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 39043 _cell_measurement_theta_min 2.20 _cell_measurement_theta_max 75.76 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.271 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1012 _exptl_absorpt_coefficient_mu 1.734 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.834 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Nova Cu X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Oxford Diffraction SuperNova' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 40851 _diffrn_reflns_av_R_equivalents 0.0300 _diffrn_reflns_av_sigmaI/netI 0.0115 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 6.53 _diffrn_reflns_theta_max 74.48 _reflns_number_total 5207 _reflns_number_gt 5193 _reflns_threshold_expression I>2/s(I) _computing_data_collection 'CrysAlis Pro (Agilent Technologies, 2010)' _computing_cell_refinement 'CrysAlis Pro (Agilent Technologies, 2010)' _computing_data_reduction 'CrysAlis Pro (Agilent Technologies, 2010)' _computing_structure_solution 'SIR2004 (Burla et al., 2005)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; Ortep III for Windows (Farrugia, 1997) ; _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0980P)^2^+0.9559P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _chemical_absolute_configuration syn _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.12(4) _refine_ls_number_reflns 5207 _refine_ls_number_parameters 655 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0472 _refine_ls_R_factor_gt 0.0471 _refine_ls_wR_factor_ref 0.1383 _refine_ls_wR_factor_gt 0.1382 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N2 N 0.1667(3) 0.60073(13) 0.60558(17) 0.0260(5) Uani 1 1 d . . . H1N2 H 0.1454 0.5569 0.6063 0.039 Uiso 1 1 d R . . N38 N 0.4232(2) 0.74321(12) 0.61886(17) 0.0221(4) Uani 1 1 d . . . H1N3 H 0.4403 0.7689 0.5691 0.033 Uiso 1 1 d R . . H2N3 H 0.3284 0.7436 0.6261 0.033 Uiso 1 1 d R . . O1 O -0.0588(2) 0.58422(12) 0.44530(15) 0.0307(5) Uani 1 1 d . . . H1 H -0.1150 0.5739 0.3904 0.046 Uiso 1 1 calc R . . O4 O 0.4691(2) 0.69701(11) 0.40034(15) 0.0279(4) Uani 1 1 d . . . H4O H 0.4730 0.7023 0.3406 0.042 Uiso 1 1 calc R . . O6 O 0.1613(2) 0.64349(13) 0.04867(15) 0.0320(5) Uani 1 1 d . . . O8 O -0.1548(2) 0.58411(13) 0.26017(16) 0.0338(5) Uani 1 1 d . . . O11 O 0.4788(2) 0.71080(13) 0.21597(17) 0.0342(5) Uani 1 1 d . A . O12 O 0.4075(3) 0.63378(12) 0.02889(15) 0.0325(5) Uani 1 1 d . . . O15 O 0.1579(2) 0.70067(11) 0.68086(16) 0.0305(4) Uani 1 1 d . . . O21 O 0.4002(2) 0.38221(11) 0.66390(15) 0.0273(4) Uani 1 1 d . . . H21O H 0.3759 0.3638 0.7126 0.041 Uiso 1 1 calc R . . O23 O 0.5437(2) 0.34366(10) 0.51855(14) 0.0259(4) Uani 1 1 d . . . H23O H 0.4758 0.3400 0.5498 0.039 Uiso 1 1 calc R . . O25 O 0.7230(2) 0.46006(10) 0.37391(15) 0.0249(4) Uani 1 1 d . . . O27 O 0.4618(3) 0.41922(13) 0.16931(17) 0.0397(6) Uani 1 1 d . A . O35 O 0.7529(3) 0.35116(12) 0.3450(2) 0.0424(6) Uani 1 1 d . . . C1 C 0.0685(3) 0.61211(14) 0.4296(2) 0.0236(5) Uani 1 1 d . . . C2 C 0.1834(3) 0.62502(14) 0.5113(2) 0.0240(5) Uani 1 1 d . . . C3 C 0.3157(3) 0.65544(14) 0.4993(2) 0.0227(5) Uani 1 1 d . . . C4 C 0.3358(3) 0.66981(14) 0.4045(2) 0.0222(5) Uani 1 1 d . . . C5 C 0.2395(3) 0.66163(14) 0.2184(2) 0.0235(5) Uani 1 1 d . A . C6 C 0.1254(3) 0.63777(16) 0.1395(2) 0.0271(6) Uani 1 1 d . . . C7 C -0.0066(3) 0.61129(18) 0.1480(2) 0.0324(7) Uani 1 1 d . . . C8 C -0.0324(3) 0.60657(15) 0.2467(2) 0.0261(6) Uani 1 1 d . . . C9 C 0.0875(3) 0.62582(14) 0.3326(2) 0.0227(5) Uani 1 1 d . . . C10 C 0.2232(3) 0.65415(13) 0.3196(2) 0.0213(5) Uani 1 1 d . . . C11 C 0.3527(3) 0.68546(14) 0.1769(2) 0.0253(5) Uani 1 1 d . . . C12 C 0.3061(3) 0.67462(17) 0.0640(2) 0.0291(6) Uani 1 1 d . A . C13 C 0.2910(4) 0.73863(19) 0.0041(3) 0.0397(8) Uani 1 1 d . . . H13A H 0.2603 0.7281 -0.0669 0.060 Uiso 1 1 calc R A . H13B H 0.3872 0.7619 0.0174 0.060 Uiso 1 1 calc R . . H13C H 0.2159 0.7674 0.0231 0.060 Uiso 1 1 calc R . . C14 C -0.1234(5) 0.5867(3) 0.0615(3) 0.0592(13) Uani 1 1 d . . . H14A H -0.0887 0.5928 0.0000 0.089 Uiso 1 1 calc R . . H14B H -0.2158 0.6120 0.0572 0.089 Uiso 1 1 calc R . . H14C H -0.1423 0.5392 0.0706 0.089 Uiso 1 1 calc R . . C15 C 0.1472(3) 0.63902(15) 0.6811(2) 0.0247(5) Uani 1 1 d . . . C16 C 0.1068(3) 0.60264(16) 0.7663(2) 0.0266(6) Uani 1 1 d . . . C17 C 0.1890(3) 0.55257(17) 0.8150(2) 0.0291(6) Uani 1 1 d . . . H17A H 0.1526 0.5318 0.8666 0.044 Uiso 1 1 calc R . . C18 C 0.3284(3) 0.52679(16) 0.7969(2) 0.0286(6) Uani 1 1 d . . . H18A H 0.3782 0.5528 0.7569 0.043 Uiso 1 1 calc R . . C19 C 0.3910(3) 0.46923(16) 0.8326(2) 0.0279(6) Uani 1 1 d . . . H19A H 0.3424 0.4431 0.8732 0.042 Uiso 1 1 calc R . . C20 C 0.5352(3) 0.44324(15) 0.8119(2) 0.0261(6) Uani 1 1 d . . . H20A H 0.5591 0.3997 0.8474 0.039 Uiso 1 1 calc R . . C21 C 0.5159(3) 0.43065(14) 0.69941(19) 0.0221(5) Uani 1 1 d . . . H21A H 0.4817 0.4737 0.6650 0.033 Uiso 1 1 calc R . . C22 C 0.6583(3) 0.41002(14) 0.6668(2) 0.0227(5) Uani 1 1 d . . . H22A H 0.7317 0.4472 0.6862 0.034 Uiso 1 1 calc R . . C23 C 0.6325(3) 0.40190(14) 0.55314(19) 0.0215(5) Uani 1 1 d . . . H23A H 0.7326 0.3943 0.5383 0.032 Uiso 1 1 calc R . . C24 C 0.5629(3) 0.46288(14) 0.4904(2) 0.0215(5) Uani 1 1 d . . . H24A H 0.4555 0.4654 0.4933 0.032 Uiso 1 1 calc R . . C25 C 0.5691(3) 0.45028(14) 0.38145(19) 0.0214(5) Uani 1 1 d . . . H25A H 0.5414 0.4037 0.3649 0.032 Uiso 1 1 d R . . C26 C 0.4688(3) 0.49583(15) 0.3046(2) 0.0270(6) Uani 1 1 d . A . H26A H 0.4916 0.5423 0.3248 0.040 Uiso 1 1 d R . . C27 C 0.5012(4) 0.48613(17) 0.2008(2) 0.0322(6) Uani 1 1 d . . . H27A H 0.6046 0.4929 0.2047 0.048 Uiso 1 1 d R A . C28 C 0.4118(4) 0.5336(2) 0.1249(3) 0.0281(12) Uani 0.867(14) 1 d P A 1 H28 H 0.3076 0.5273 0.1006 0.042 Uiso 0.867(14) 1 calc PR A 1 C29 C 0.4802(5) 0.5839(2) 0.0932(3) 0.0286(12) Uani 0.867(14) 1 d P A 1 H29 H 0.5856 0.5865 0.1152 0.043 Uiso 0.867(14) 1 calc PR A 1 C28' C 0.508(3) 0.5537(11) 0.1440(17) 0.018(7) Uani 0.133(14) 1 d P A 2 H28B H 0.5875 0.5844 0.1633 0.027 Uiso 0.133(14) 1 calc PR A 2 C29' C 0.399(3) 0.5645(11) 0.0706(18) 0.018(7) Uani 0.133(14) 1 d P A 2 H29B H 0.3227 0.5331 0.0452 0.027 Uiso 0.133(14) 1 calc PR A 2 C30 C -0.0320(4) 0.6279(2) 0.7931(3) 0.0398(8) Uani 1 1 d . . . H30A H -0.0517 0.6017 0.8488 0.060 Uiso 1 1 calc R . . H30B H -0.1165 0.6236 0.7357 0.060 Uiso 1 1 calc R . . H30C H -0.0188 0.6750 0.8126 0.060 Uiso 1 1 calc R . . C31 C 0.6635(4) 0.4918(2) 0.8516(2) 0.0372(7) Uani 1 1 d . . . H31A H 0.6729 0.4987 0.9230 0.056 Uiso 1 1 calc R . . H31B H 0.6431 0.5346 0.8167 0.056 Uiso 1 1 calc R . . H31C H 0.7568 0.4731 0.8404 0.056 Uiso 1 1 calc R . . C32 C 0.7312(3) 0.34701(16) 0.7198(2) 0.0288(6) Uani 1 1 d . . . H32A H 0.7468 0.3529 0.7920 0.043 Uiso 1 1 calc R . . H32B H 0.8274 0.3394 0.7026 0.043 Uiso 1 1 calc R . . H32C H 0.6659 0.3085 0.6989 0.043 Uiso 1 1 calc R . . C33 C 0.6362(3) 0.52966(15) 0.5281(2) 0.0258(5) Uani 1 1 d . . . H33A H 0.6307 0.5363 0.5975 0.039 Uiso 1 1 calc R . . H33B H 0.5837 0.5661 0.4873 0.039 Uiso 1 1 calc R . . H33C H 0.7409 0.5292 0.5236 0.039 Uiso 1 1 calc R . . C34 C 0.3043(4) 0.48231(19) 0.3043(2) 0.0355(7) Uani 1 1 d . . . H34A H 0.2403 0.5111 0.2549 0.053 Uiso 1 1 calc R A . H34B H 0.2868 0.4919 0.3704 0.053 Uiso 1 1 calc R . . H34C H 0.2808 0.4354 0.2875 0.053 Uiso 1 1 calc R . . C35 C 0.8004(3) 0.40711(15) 0.3534(2) 0.0268(6) Uani 1 1 d . . . C36 C 0.9521(4) 0.42767(18) 0.3412(3) 0.0377(7) Uani 1 1 d . . . H36A H 1.0067 0.3882 0.3270 0.057 Uiso 1 1 calc R . . H36B H 1.0073 0.4488 0.4027 0.057 Uiso 1 1 calc R . . H36C H 0.9414 0.4595 0.2860 0.057 Uiso 1 1 calc R . . C37 C 0.5391(6) 0.3965(2) 0.0970(3) 0.0515(10) Uani 1 1 d . . . H37A H 0.5083 0.3507 0.0773 0.077 Uiso 1 1 calc R A . H37B H 0.6468 0.3975 0.1254 0.077 Uiso 1 1 calc R . . H37C H 0.5154 0.4256 0.0385 0.077 Uiso 1 1 calc R . . C38 C 0.4392(3) 0.67261(14) 0.5875(2) 0.0232(5) Uani 1 1 d . . . H38A H 0.4357 0.6420 0.6433 0.035 Uiso 1 1 calc R . . H38B H 0.5370 0.6668 0.5699 0.035 Uiso 1 1 calc R . . C39 C 0.5381(3) 0.76242(15) 0.7109(2) 0.0265(6) Uani 1 1 d . . . H39A H 0.6390 0.7514 0.7017 0.040 Uiso 1 1 calc R . . H39B H 0.5337 0.8112 0.7217 0.040 Uiso 1 1 calc R . . C40 C 0.5108(4) 0.72606(18) 0.8001(2) 0.0314(6) Uani 1 1 d . . . H40A H 0.4140 0.7294 0.8130 0.047 Uiso 1 1 calc R . . C41 C 0.6085(5) 0.6906(2) 0.8608(3) 0.0474(9) Uani 1 1 d . . . H41A H 0.7066 0.6860 0.8505 0.071 Uiso 1 1 calc R . . H41B H 0.5821 0.6691 0.9157 0.071 Uiso 1 1 calc R . . O1A O 0.1545(3) 0.45924(13) 0.58273(19) 0.0378(5) Uani 1 1 d . . . H1A H 0.2338 0.4383 0.6060 0.057 Uiso 1 1 calc R . . C1A C 0.0371(4) 0.4305(2) 0.6180(4) 0.0568(11) Uani 1 1 d . . . H1A1 H 0.0241 0.3839 0.5960 0.085 Uiso 1 1 calc R . . H1A2 H -0.0552 0.4553 0.5916 0.085 Uiso 1 1 calc R . . H1A3 H 0.0606 0.4322 0.6908 0.085 Uiso 1 1 calc R . . O1C O 0.6851(18) 0.8013(9) 0.2049(13) 0.036(2) Uani 0.57(3) 1 d P B 3 H1C H 0.6129 0.7748 0.1885 0.053 Uiso 0.57(3) 1 calc PR B 3 C1C C 0.8195(11) 0.7640(6) 0.2481(13) 0.064(4) Uani 0.57(3) 1 d P B 3 H1C1 H 0.8975 0.7949 0.2816 0.095 Uiso 0.57(3) 1 calc PR B 3 H1C2 H 0.8536 0.7401 0.1955 0.095 Uiso 0.57(3) 1 calc PR B 3 H1C3 H 0.7979 0.7319 0.2966 0.095 Uiso 0.57(3) 1 calc PR B 3 O1C' O 0.653(3) 0.8082(13) 0.1783(18) 0.039(3) Uani 0.43(3) 1 d P B 4 H1C' H 0.6039 0.7769 0.1958 0.059 Uiso 0.43(3) 1 calc PR B 4 C1C' C 0.8033(18) 0.7844(8) 0.176(3) 0.087(10) Uani 0.43(3) 1 d P B 4 H1C4 H 0.8756 0.8204 0.1976 0.131 Uiso 0.43(3) 1 calc PR B 4 H1C5 H 0.8055 0.7705 0.1087 0.131 Uiso 0.43(3) 1 calc PR B 4 H1C6 H 0.8290 0.7463 0.2217 0.131 Uiso 0.43(3) 1 calc PR B 4 C1D C -0.157(2) 0.7559(13) 0.5216(17) 0.112(8) Uani 0.742(11) 1 d P C 5 H1D1 H -0.2497 0.7793 0.4904 0.168 Uiso 0.742(11) 1 calc PR C 5 H1D2 H -0.1662 0.7086 0.5028 0.168 Uiso 0.742(11) 1 calc PR C 5 H1D3 H -0.0735 0.7758 0.4991 0.168 Uiso 0.742(11) 1 calc PR C 5 O1D O -0.1318(5) 0.7617(3) 0.6285(5) 0.077(2) Uani 0.742(11) 1 d P C 5 H1D H -0.0606 0.7368 0.6555 0.116 Uiso 0.742(11) 1 calc PR C 5 C1D' C -0.170(5) 0.7549(16) 0.517(2) 0.047(7) Uiso 0.258(11) 1 d P C 6 H1D4 H -0.2281 0.7894 0.5414 0.071 Uiso 0.258(11) 1 calc PR C 6 H1D5 H -0.2002 0.7525 0.4444 0.071 Uiso 0.258(11) 1 calc PR C 6 H1D6 H -0.0634 0.7660 0.5370 0.071 Uiso 0.258(11) 1 calc PR C 6 O1D' O -0.1978(14) 0.6857(8) 0.5629(11) 0.063(4) Uani 0.258(11) 1 d P C 6 H1D' H -0.1433 0.6566 0.5452 0.095 Uiso 0.258(11) 1 calc PR C 6 Cl2B Cl 0.9299(4) 0.81735(15) 0.8423(2) 0.0946(7) Uani 0.67 1 d P . . Cl1B Cl 0.9884(4) 0.93930(19) 0.9514(3) 0.1113(10) Uani 0.67 1 d P . . Cl3B Cl 0.8473(6) 0.8305(3) 1.0300(2) 0.1447(16) Uani 0.67 1 d P . . C1B C 0.835(2) 0.9168(9) 0.9670(12) 0.068(4) Uani 0.33 1 d P D 7 H1B1 H 0.7630 0.9144 0.9017 0.102 Uiso 0.33 1 d PR D 7 H1B2 H 0.7970 0.9500 1.0084 0.102 Uiso 0.33 1 d PR D 7 C1B' C 0.8724(11) 0.8727(6) 0.9211(7) 0.082(3) Uani 0.67 1 d P D 8 H1BA H 0.7716 0.8891 0.8888 0.123 Uiso 0.67 1 d PR D 8 H1BB H 0.8650 0.8490 0.9828 0.123 Uiso 0.22 1 d PR D 8 H1BC H 0.9143 0.8413 0.8791 0.123 Uiso 0.22 1 d PR D 8 H1BD H 0.9474 0.9086 0.9399 0.123 Uiso 0.22 1 d PR D 8 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 N2 0.0352(12) 0.0236(12) 0.0210(11) 0.0027(9) 0.0102(9) -0.0028(10) N38 0.0230(10) 0.0198(11) 0.0231(11) 0.0006(9) 0.0041(8) 0.0002(8) O1 0.0276(10) 0.0401(12) 0.0268(10) 0.0010(9) 0.0113(8) -0.0088(9) O4 0.0242(9) 0.0356(11) 0.0247(9) 0.0003(8) 0.0074(7) -0.0074(8) O6 0.0339(10) 0.0441(13) 0.0189(9) 0.0057(9) 0.0075(8) -0.0041(10) O8 0.0244(10) 0.0464(13) 0.0305(10) 0.0048(10) 0.0058(8) -0.0062(9) O11 0.0319(10) 0.0394(12) 0.0348(11) -0.0006(10) 0.0150(9) -0.0114(10) O12 0.0421(11) 0.0351(12) 0.0244(9) 0.0072(9) 0.0164(8) 0.0081(10) O15 0.0332(10) 0.0268(11) 0.0350(11) 0.0008(9) 0.0151(9) 0.0037(8) O21 0.0246(9) 0.0305(10) 0.0270(9) -0.0014(8) 0.0063(7) -0.0058(8) O23 0.0324(10) 0.0219(9) 0.0249(9) -0.0014(8) 0.0093(7) -0.0061(8) O25 0.0275(9) 0.0218(9) 0.0284(9) -0.0010(8) 0.0126(7) -0.0014(8) O27 0.0525(14) 0.0385(13) 0.0294(11) -0.0080(10) 0.0121(10) 0.0053(11) O35 0.0354(11) 0.0232(11) 0.0736(18) -0.0023(11) 0.0230(12) 0.0015(10) C1 0.0244(12) 0.0251(13) 0.0232(12) 0.0009(10) 0.0095(10) -0.0030(10) C2 0.0301(13) 0.0226(13) 0.0210(12) 0.0023(10) 0.0092(10) -0.0011(10) C3 0.0242(12) 0.0204(12) 0.0241(12) 0.0003(10) 0.0069(10) 0.0008(10) C4 0.0232(12) 0.0192(12) 0.0257(13) -0.0011(10) 0.0085(10) -0.0004(10) C5 0.0275(12) 0.0214(12) 0.0229(12) 0.0012(10) 0.0084(10) -0.0005(10) C6 0.0323(14) 0.0311(15) 0.0186(12) 0.0045(11) 0.0073(10) 0.0011(12) C7 0.0273(14) 0.0455(18) 0.0229(13) 0.0050(13) 0.0025(11) -0.0040(13) C8 0.0232(13) 0.0286(14) 0.0258(13) 0.0053(11) 0.0041(10) -0.0014(11) C9 0.0238(12) 0.0228(13) 0.0223(12) 0.0024(10) 0.0068(10) 0.0006(10) C10 0.0238(12) 0.0193(12) 0.0227(12) 0.0021(10) 0.0092(10) 0.0016(10) C11 0.0294(13) 0.0226(13) 0.0259(13) 0.0022(10) 0.0107(10) 0.0005(11) C12 0.0331(14) 0.0320(15) 0.0251(13) 0.0045(12) 0.0127(11) 0.0008(12) C13 0.0465(18) 0.0379(18) 0.0397(17) 0.0153(15) 0.0201(14) 0.0082(15) C14 0.0406(19) 0.106(4) 0.0268(16) 0.008(2) -0.0013(14) -0.032(2) C15 0.0225(12) 0.0290(14) 0.0240(12) 0.0027(11) 0.0079(10) 0.0029(11) C16 0.0288(13) 0.0304(14) 0.0225(12) 0.0002(11) 0.0097(10) -0.0003(11) C17 0.0328(14) 0.0359(15) 0.0215(12) 0.0022(11) 0.0121(11) 0.0027(12) C18 0.0314(14) 0.0316(15) 0.0241(13) 0.0025(11) 0.0092(11) 0.0015(12) C19 0.0314(14) 0.0317(15) 0.0211(12) 0.0018(11) 0.0074(10) 0.0015(12) C20 0.0300(14) 0.0288(14) 0.0191(12) 0.0026(10) 0.0045(10) 0.0010(11) C21 0.0223(12) 0.0244(13) 0.0188(12) 0.0009(10) 0.0034(9) -0.0031(10) C22 0.0225(12) 0.0230(13) 0.0218(12) 0.0000(10) 0.0034(9) -0.0018(10) C23 0.0222(11) 0.0203(12) 0.0223(12) -0.0009(10) 0.0058(9) -0.0012(10) C24 0.0225(12) 0.0208(12) 0.0227(12) 0.0017(10) 0.0078(9) 0.0006(10) C25 0.0210(12) 0.0211(12) 0.0228(12) 0.0004(10) 0.0066(9) 0.0014(10) C26 0.0366(15) 0.0225(13) 0.0220(13) 0.0009(10) 0.0072(11) 0.0048(11) C27 0.0447(17) 0.0297(15) 0.0229(14) 0.0011(12) 0.0091(12) 0.0047(13) C28 0.031(2) 0.028(2) 0.0244(19) 0.0012(16) 0.0050(13) -0.0011(16) C29 0.027(2) 0.034(2) 0.0272(18) 0.0041(18) 0.0110(14) 0.0021(19) C28' 0.025(11) 0.014(8) 0.020(10) 0.000(7) 0.015(8) -0.004(6) C29' 0.025(11) 0.014(8) 0.020(10) 0.000(7) 0.015(8) -0.004(6) C30 0.0407(17) 0.052(2) 0.0338(15) 0.0114(15) 0.0224(13) 0.0132(16) C31 0.0312(15) 0.049(2) 0.0279(14) -0.0110(14) 0.0001(12) -0.0021(14) C32 0.0277(13) 0.0291(14) 0.0288(14) 0.0049(12) 0.0047(11) 0.0047(12) C33 0.0329(14) 0.0198(13) 0.0256(13) -0.0011(10) 0.0082(11) -0.0003(11) C34 0.0317(15) 0.0447(18) 0.0287(14) 0.0023(13) 0.0041(11) 0.0127(14) C35 0.0276(13) 0.0260(14) 0.0289(13) 0.0005(11) 0.0106(11) 0.0012(11) C36 0.0331(16) 0.0351(17) 0.0513(19) -0.0019(15) 0.0226(14) -0.0021(13) C37 0.081(3) 0.050(2) 0.0274(16) -0.0010(16) 0.0203(17) 0.020(2) C38 0.0271(12) 0.0192(12) 0.0238(12) 0.0011(10) 0.0067(10) 0.0022(10) C39 0.0289(13) 0.0258(13) 0.0229(12) -0.0009(11) 0.0017(10) -0.0002(11) C40 0.0319(14) 0.0402(17) 0.0239(13) -0.0029(12) 0.0102(11) 0.0018(13) C41 0.0474(19) 0.065(3) 0.0329(16) 0.0160(17) 0.0148(14) 0.0140(18) O1A 0.0300(11) 0.0310(11) 0.0476(13) 0.0041(10) -0.0010(9) -0.0012(9) C1A 0.0277(17) 0.040(2) 0.103(4) 0.001(2) 0.0146(19) -0.0040(15) O1C 0.031(5) 0.026(4) 0.054(7) -0.006(4) 0.018(4) -0.004(4) C1C 0.056(5) 0.046(5) 0.094(9) -0.013(5) 0.027(5) 0.003(4) O1C' 0.038(9) 0.030(6) 0.056(10) -0.004(6) 0.023(6) -0.001(5) C1C' 0.056(8) 0.049(8) 0.17(3) -0.023(12) 0.063(12) -0.006(6) C1D 0.053(6) 0.143(13) 0.141(14) 0.049(9) 0.024(6) 0.027(7) O1D 0.053(3) 0.083(4) 0.103(4) 0.031(3) 0.032(3) 0.029(3) O1D' 0.049(7) 0.070(9) 0.072(9) 0.004(7) 0.019(6) -0.007(6) Cl2B 0.120(2) 0.0793(15) 0.0850(15) -0.0038(12) 0.0247(14) -0.0041(14) Cl1B 0.1005(19) 0.109(2) 0.112(2) -0.0199(18) -0.0010(15) -0.0226(17) Cl3B 0.188(4) 0.174(4) 0.0708(16) 0.030(2) 0.026(2) -0.030(3) C1B 0.086(11) 0.062(9) 0.060(8) 0.002(7) 0.026(8) 0.028(8) C1B' 0.079(5) 0.091(7) 0.068(5) 0.025(5) -0.001(4) -0.006(5) _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 N2 C15 1.338(4) . ? N2 C2 1.430(3) . ? N2 H1N2 0.9001 . ? N38 C38 1.496(3) . ? N38 C39 1.506(4) . ? N38 H1N3 0.9008 . ? N38 H2N3 0.9004 . ? O1 C1 1.360(3) . ? O1 H1 0.8400 . ? O4 C4 1.355(3) . ? O4 H4O 0.8400 . ? O6 C6 1.371(3) . ? O6 C12 1.442(4) . ? O8 C8 1.266(4) . ? O11 C11 1.269(4) . ? O12 C29 1.401(5) . ? O12 C12 1.408(4) . ? O12 C29' 1.51(2) . ? O15 C15 1.238(4) . ? O21 C21 1.442(3) . ? O21 H21O 0.8400 . ? O23 C23 1.441(3) . ? O23 H23O 0.8400 . ? O25 C35 1.343(4) . ? O25 C25 1.458(3) . ? O27 C37 1.426(4) . ? O27 C27 1.429(4) . ? O35 C35 1.199(4) . ? C1 C2 1.384(4) . ? C1 C9 1.416(4) . ? C2 C3 1.405(4) . ? C3 C4 1.393(4) . ? C3 C38 1.505(4) . ? C4 C10 1.412(4) . ? C5 C11 1.383(4) . ? C5 C6 1.413(4) . ? C5 C10 1.447(4) . ? C6 C7 1.356(4) . ? C7 C8 1.437(4) . ? C7 C14 1.497(5) . ? C8 C9 1.475(4) . ? C9 C10 1.419(4) . ? C11 C12 1.535(4) . ? C12 C13 1.515(4) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C16 1.500(4) . ? C16 C17 1.341(4) . ? C16 C30 1.497(4) . ? C17 C18 1.456(4) . ? C17 H17A 0.9500 . ? C18 C19 1.331(4) . ? C18 H18A 0.9500 . ? C19 C20 1.513(4) . ? C19 H19A 0.9500 . ? C20 C31 1.531(5) . ? C20 C21 1.543(4) . ? C20 H20A 1.0000 . ? C21 C22 1.536(4) . ? C21 H21A 1.0000 . ? C22 C32 1.534(4) . ? C22 C23 1.541(4) . ? C22 H22A 1.0000 . ? C23 C24 1.549(4) . ? C23 H23A 1.0000 . ? C24 C33 1.534(4) . ? C24 C25 1.539(4) . ? C24 H24A 1.0000 . ? C25 C26 1.538(4) . ? C25 H25A 0.9800 . ? C26 C34 1.537(5) . ? C26 C27 1.541(4) . ? C26 H26A 0.9799 . ? C27 C28 1.512(5) . ? C27 C28' 1.57(2) . ? C27 H27A 0.9500 . ? C28 C29 1.313(8) . ? C28 H28 0.9500 . ? C29 H29 0.9500 . ? C28' C29' 1.27(4) . ? C28' H28B 0.9500 . ? C29' H29B 0.9500 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? C35 C36 1.501(4) . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? C38 H38A 0.9900 . ? C38 H38B 0.9900 . ? C39 C40 1.500(4) . ? C39 H39A 0.9900 . ? C39 H39B 0.9900 . ? C40 C41 1.293(5) . ? C40 H40A 0.9500 . ? C41 H41A 0.9500 . ? C41 H41B 0.9500 . ? O1A C1A 1.405(5) . ? O1A H1A 0.8400 . ? C1A H1A1 0.9800 . ? C1A H1A2 0.9800 . ? C1A H1A3 0.9800 . ? O1C C1C 1.451(16) . ? O1C H1C 0.8400 . ? C1C H1C1 0.9800 . ? C1C H1C2 0.9800 . ? C1C H1C3 0.9800 . ? O1C' C1C' 1.47(3) . ? O1C' H1C' 0.8400 . ? C1C' H1C4 0.9800 . ? C1C' H1C5 0.9800 . ? C1C' H1C6 0.9800 . ? C1D O1D 1.45(2) . ? C1D H1D1 0.9800 . ? C1D H1D2 0.9800 . ? C1D H1D3 0.9800 . ? O1D H1D 0.8400 . ? C1D' O1D' 1.57(4) . ? C1D' H1D4 0.9800 . ? C1D' H1D5 0.9800 . ? C1D' H1D6 0.9800 . ? O1D' H1D' 0.8400 . ? Cl2B C1B' 1.718(13) . ? Cl1B C1B 1.546(19) . ? Cl1B C1B' 1.700(11) . ? Cl3B C1B' 1.784(10) . ? Cl3B C1B 1.925(17) . ? C1B H1B1 0.9900 . ? C1B H1B2 0.9901 . ? C1B' H1BA 0.9900 . ? C1B' H1BB 0.9899 . ? C1B' H1BC 0.9900 . ? C1B' H1BD 0.9900 . ? 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 C15 N2 C2 125.1(3) . . ? C15 N2 H1N2 118.8 . . ? C2 N2 H1N2 114.2 . . ? C38 N38 C39 112.9(2) . . ? C38 N38 H1N3 105.9 . . ? C39 N38 H1N3 106.6 . . ? C38 N38 H2N3 101.7 . . ? C39 N38 H2N3 114.6 . . ? H1N3 N38 H2N3 114.9 . . ? C1 O1 H1 109.5 . . ? C4 O4 H4O 109.5 . . ? C6 O6 C12 107.9(2) . . ? C29 O12 C12 117.0(2) . . ? C12 O12 C29' 107.9(8) . . ? C21 O21 H21O 109.5 . . ? C23 O23 H23O 109.5 . . ? C35 O25 C25 118.7(2) . . ? C37 O27 C27 112.3(3) . . ? O1 C1 C2 118.2(2) . . ? O1 C1 C9 121.8(2) . . ? C2 C1 C9 119.9(3) . . ? C1 C2 C3 120.4(2) . . ? C1 C2 N2 117.3(3) . . ? C3 C2 N2 122.1(2) . . ? C4 C3 C2 120.3(2) . . ? C4 C3 C38 118.4(2) . . ? C2 C3 C38 121.3(2) . . ? O4 C4 C3 115.9(2) . . ? O4 C4 C10 123.7(2) . . ? C3 C4 C10 120.3(2) . . ? C11 C5 C6 107.2(2) . . ? C11 C5 C10 133.5(3) . . ? C6 C5 C10 119.2(2) . . ? C7 C6 O6 121.3(3) . . ? C7 C6 C5 126.0(3) . . ? O6 C6 C5 112.7(2) . . ? C6 C7 C8 116.9(3) . . ? C6 C7 C14 123.7(3) . . ? C8 C7 C14 119.4(3) . . ? O8 C8 C7 120.5(3) . . ? O8 C8 C9 120.1(3) . . ? C7 C8 C9 119.3(3) . . ? C1 C9 C10 119.9(2) . . ? C1 C9 C8 118.6(2) . . ? C10 C9 C8 121.4(2) . . ? C4 C10 C9 119.0(2) . . ? C4 C10 C5 124.1(2) . . ? C9 C10 C5 116.8(2) . . ? O11 C11 C5 131.7(3) . . ? O11 C11 C12 120.3(3) . . ? C5 C11 C12 108.0(2) . . ? O12 C12 O6 111.2(3) . . ? O12 C12 C13 106.8(2) . . ? O6 C12 C13 108.6(3) . . ? O12 C12 C11 112.2(2) . . ? O6 C12 C11 104.2(2) . . ? C13 C12 C11 113.9(3) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C7 C14 H14A 109.5 . . ? C7 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C7 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O15 C15 N2 123.0(3) . . ? O15 C15 C16 121.3(3) . . ? N2 C15 C16 115.7(3) . . ? C17 C16 C30 123.0(3) . . ? C17 C16 C15 122.9(3) . . ? C30 C16 C15 114.1(3) . . ? C16 C17 C18 126.7(3) . . ? C16 C17 H17A 116.6 . . ? C18 C17 H17A 116.6 . . ? C19 C18 C17 124.5(3) . . ? C19 C18 H18A 117.7 . . ? C17 C18 H18A 117.7 . . ? C18 C19 C20 123.5(3) . . ? C18 C19 H19A 118.2 . . ? C20 C19 H19A 118.2 . . ? C19 C20 C31 110.6(3) . . ? C19 C20 C21 110.0(2) . . ? C31 C20 C21 111.5(2) . . ? C19 C20 H20A 108.2 . . ? C31 C20 H20A 108.2 . . ? C21 C20 H20A 108.2 . . ? O21 C21 C22 109.5(2) . . ? O21 C21 C20 111.1(2) . . ? C22 C21 C20 115.4(2) . . ? O21 C21 H21A 106.8 . . ? C22 C21 H21A 106.8 . . ? C20 C21 H21A 106.8 . . ? C32 C22 C21 113.0(2) . . ? C32 C22 C23 110.4(2) . . ? C21 C22 C23 112.5(2) . . ? C32 C22 H22A 106.9 . . ? C21 C22 H22A 106.9 . . ? C23 C22 H22A 106.9 . . ? O23 C23 C22 111.5(2) . . ? O23 C23 C24 108.7(2) . . ? C22 C23 C24 115.8(2) . . ? O23 C23 H23A 106.8 . . ? C22 C23 H23A 106.8 . . ? C24 C23 H23A 106.8 . . ? C33 C24 C25 111.3(2) . . ? C33 C24 C23 113.8(2) . . ? C25 C24 C23 108.4(2) . . ? C33 C24 H24A 107.7 . . ? C25 C24 H24A 107.7 . . ? C23 C24 H24A 107.7 . . ? O25 C25 C26 108.2(2) . . ? O25 C25 C24 107.5(2) . . ? C26 C25 C24 115.3(2) . . ? O25 C25 H25A 108.4 . . ? C26 C25 H25A 108.7 . . ? C24 C25 H25A 108.6 . . ? C34 C26 C25 109.5(2) . . ? C34 C26 C27 112.0(3) . . ? C25 C26 C27 110.7(2) . . ? C34 C26 H26A 108.3 . . ? C25 C26 H26A 108.0 . . ? C27 C26 H26A 108.1 . . ? O27 C27 C28 108.6(3) . . ? O27 C27 C26 108.1(3) . . ? C28 C27 C26 112.0(3) . . ? O27 C27 C28' 133.7(8) . . ? C26 C27 C28' 113.1(7) . . ? O27 C27 H27A 109.4 . . ? C28 C27 H27A 109.3 . . ? C26 C27 H27A 109.4 . . ? C29 C28 C27 119.1(4) . . ? C29 C28 H28 120.5 . . ? C27 C28 H28 120.5 . . ? C28 C29 O12 124.2(4) . . ? C28 C29 H29 117.9 . . ? O12 C29 H29 117.9 . . ? C29' C28' C27 116(2) . . ? C29' C28' H28B 122.1 . . ? C27 C28' H28B 122.1 . . ? C28' C29' O12 111(2) . . ? C28' C29' H29B 124.3 . . ? O12 C29' H29B 124.3 . . ? C16 C30 H30A 109.5 . . ? C16 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C16 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C20 C31 H31A 109.5 . . ? C20 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C20 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C22 C32 H32A 109.5 . . ? C22 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C22 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C24 C33 H33A 109.5 . . ? C24 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C24 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C26 C34 H34A 109.5 . . ? C26 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C26 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? O35 C35 O25 123.9(3) . . ? O35 C35 C36 125.0(3) . . ? O25 C35 C36 111.0(3) . . ? 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 . . ? O27 C37 H37A 109.5 . . ? O27 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? O27 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? N38 C38 C3 110.1(2) . . ? N38 C38 H38A 109.6 . . ? C3 C38 H38A 109.6 . . ? N38 C38 H38B 109.6 . . ? C3 C38 H38B 109.6 . . ? H38A C38 H38B 108.1 . . ? C40 C39 N38 110.6(2) . . ? C40 C39 H39A 109.5 . . ? N38 C39 H39A 109.5 . . ? C40 C39 H39B 109.5 . . ? N38 C39 H39B 109.5 . . ? H39A C39 H39B 108.1 . . ? C41 C40 C39 125.2(3) . . ? C41 C40 H40A 117.4 . . ? C39 C40 H40A 117.4 . . ? C40 C41 H41A 120.0 . . ? C40 C41 H41B 120.0 . . ? H41A C41 H41B 120.0 . . ? C1A O1A H1A 109.5 . . ? 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 . . ? Cl1B C1B Cl3B 111.2(9) . . ? Cl1B C1B H1B1 109.1 . . ? Cl3B C1B H1B1 109.1 . . ? Cl1B C1B H1B2 109.7 . . ? Cl3B C1B H1B2 109.6 . . ? H1B1 C1B H1B2 108.0 . . ? Cl1B C1B H1BA 105.8 . . ? H1B2 C1B H1BA 130.5 . . ? H1B2 C1B H1BB 130.5 . . ? H1B2 C1B H1BD 135.9 . . ? Cl1B C1B' Cl2B 113.3(6) . . ? Cl1B C1B' Cl3B 111.0(6) . . ? Cl2B C1B' Cl3B 110.2(6) . . ? Cl2B C1B' H1B1 128.7 . . ? Cl3B C1B' H1B1 103.7 . . ? Cl1B C1B' H1BA 108.8 . . ? Cl2B C1B' H1BA 108.7 . . ? Cl3B C1B' H1BA 104.4 . . ? Cl1B C1B' H1BB 109.1 . . ? Cl2B C1B' H1BB 109.1 . . ? H1B1 C1B' H1BB 106.6 . . ? H1BA C1B' H1BB 107.8 . . ? Cl1B C1B' H1BC 109.6 . . ? Cl3B C1B' H1BC 109.6 . . ? H1B1 C1B' H1BC 132.7 . . ? H1BA C1B' H1BC 113.4 . . ? H1BB C1B' H1BC 108.2 . . ? Cl2B C1B' H1BD 109.8 . . ? Cl3B C1B' H1BD 109.8 . . ? H1BA C1B' H1BD 113.7 . . ? H1BB C1B' H1BD 107.6 . . ? H1BC C1B' H1BD 105.9 . . ? 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 O1 C1 C2 C3 -178.3(3) . . . . ? C9 C1 C2 C3 3.9(4) . . . . ? O1 C1 C2 N2 7.3(4) . . . . ? C9 C1 C2 N2 -170.5(3) . . . . ? C15 N2 C2 C1 -111.4(3) . . . . ? C15 N2 C2 C3 74.2(4) . . . . ? C1 C2 C3 C4 -3.3(4) . . . . ? N2 C2 C3 C4 170.8(3) . . . . ? C1 C2 C3 C38 177.3(3) . . . . ? N2 C2 C3 C38 -8.5(4) . . . . ? C2 C3 C4 O4 -177.8(2) . . . . ? C38 C3 C4 O4 1.6(4) . . . . ? C2 C3 C4 C10 0.2(4) . . . . ? C38 C3 C4 C10 179.6(2) . . . . ? C12 O6 C6 C7 178.7(3) . . . . ? C12 O6 C6 C5 -1.6(3) . . . . ? C11 C5 C6 C7 -178.8(3) . . . . ? C10 C5 C6 C7 4.4(5) . . . . ? C11 C5 C6 O6 1.6(3) . . . . ? C10 C5 C6 O6 -175.2(3) . . . . ? O6 C6 C7 C8 179.1(3) . . . . ? C5 C6 C7 C8 -0.5(5) . . . . ? O6 C6 C7 C14 -0.3(6) . . . . ? C5 C6 C7 C14 -179.9(4) . . . . ? C6 C7 C8 O8 178.0(3) . . . . ? C14 C7 C8 O8 -2.6(5) . . . . ? C6 C7 C8 C9 -4.3(5) . . . . ? C14 C7 C8 C9 175.2(4) . . . . ? O1 C1 C9 C10 -179.1(3) . . . . ? C2 C1 C9 C10 -1.4(4) . . . . ? O1 C1 C9 C8 -2.6(4) . . . . ? C2 C1 C9 C8 175.2(3) . . . . ? O8 C8 C9 C1 6.6(4) . . . . ? C7 C8 C9 C1 -171.2(3) . . . . ? O8 C8 C9 C10 -176.9(3) . . . . ? C7 C8 C9 C10 5.3(4) . . . . ? O4 C4 C10 C9 -179.9(3) . . . . ? C3 C4 C10 C9 2.2(4) . . . . ? O4 C4 C10 C5 3.7(4) . . . . ? C3 C4 C10 C5 -174.2(3) . . . . ? C1 C9 C10 C4 -1.7(4) . . . . ? C8 C9 C10 C4 -178.1(3) . . . . ? C1 C9 C10 C5 175.0(3) . . . . ? C8 C9 C10 C5 -1.5(4) . . . . ? C11 C5 C10 C4 -2.4(5) . . . . ? C6 C5 C10 C4 173.3(3) . . . . ? C11 C5 C10 C9 -178.9(3) . . . . ? C6 C5 C10 C9 -3.2(4) . . . . ? C6 C5 C11 O11 -178.8(3) . . . . ? C10 C5 C11 O11 -2.7(6) . . . . ? C6 C5 C11 C12 -0.8(3) . . . . ? C10 C5 C11 C12 175.3(3) . . . . ? C29 O12 C12 O6 -84.0(4) . . . . ? C29' O12 C12 O6 -49.5(12) . . . . ? C29 O12 C12 C13 157.8(3) . . . . ? C29' O12 C12 C13 -167.8(12) . . . . ? C29 O12 C12 C11 32.3(4) . . . . ? C29' O12 C12 C11 66.8(12) . . . . ? C6 O6 C12 O12 122.1(3) . . . . ? C6 O6 C12 C13 -120.7(3) . . . . ? C6 O6 C12 C11 1.0(3) . . . . ? O11 C11 C12 O12 57.8(4) . . . . ? C5 C11 C12 O12 -120.5(3) . . . . ? O11 C11 C12 O6 178.2(3) . . . . ? C5 C11 C12 O6 -0.1(3) . . . . ? O11 C11 C12 C13 -63.7(4) . . . . ? C5 C11 C12 C13 118.0(3) . . . . ? C2 N2 C15 O15 -8.2(5) . . . . ? C2 N2 C15 C16 170.2(3) . . . . ? O15 C15 C16 C17 -126.6(3) . . . . ? N2 C15 C16 C17 55.1(4) . . . . ? O15 C15 C16 C30 52.4(4) . . . . ? N2 C15 C16 C30 -125.9(3) . . . . ? C30 C16 C17 C18 -177.1(3) . . . . ? C15 C16 C17 C18 1.8(5) . . . . ? C16 C17 C18 C19 -166.0(3) . . . . ? C17 C18 C19 C20 179.4(3) . . . . ? C18 C19 C20 C31 61.0(4) . . . . ? C18 C19 C20 C21 -62.6(4) . . . . ? C19 C20 C21 O21 -60.0(3) . . . . ? C31 C20 C21 O21 176.9(3) . . . . ? C19 C20 C21 C22 174.8(2) . . . . ? C31 C20 C21 C22 51.7(3) . . . . ? O21 C21 C22 C32 -68.9(3) . . . . ? C20 C21 C22 C32 57.2(3) . . . . ? O21 C21 C22 C23 56.9(3) . . . . ? C20 C21 C22 C23 -177.0(2) . . . . ? C32 C22 C23 O23 56.4(3) . . . . ? C21 C22 C23 O23 -70.8(3) . . . . ? C32 C22 C23 C24 -178.5(2) . . . . ? C21 C22 C23 C24 54.3(3) . . . . ? O23 C23 C24 C33 173.0(2) . . . . ? C22 C23 C24 C33 46.5(3) . . . . ? O23 C23 C24 C25 -62.6(3) . . . . ? C22 C23 C24 C25 170.9(2) . . . . ? C35 O25 C25 C26 -121.6(3) . . . . ? C35 O25 C25 C24 113.3(3) . . . . ? C33 C24 C25 O25 50.8(3) . . . . ? C23 C24 C25 O25 -75.0(3) . . . . ? C33 C24 C25 C26 -69.9(3) . . . . ? C23 C24 C25 C26 164.3(2) . . . . ? O25 C25 C26 C34 175.2(2) . . . . ? C24 C25 C26 C34 -64.5(3) . . . . ? O25 C25 C26 C27 51.2(3) . . . . ? C24 C25 C26 C27 171.5(2) . . . . ? C37 O27 C27 C28 81.8(4) . . . . ? C37 O27 C27 C26 -156.5(3) . . . . ? C37 O27 C27 C28' 51.4(12) . . . . ? C34 C26 C27 O27 -58.2(3) . . . . ? C25 C26 C27 O27 64.3(3) . . . . ? C34 C26 C27 C28 61.4(4) . . . . ? C25 C26 C27 C28 -176.1(3) . . . . ? C34 C26 C27 C28' 100.2(10) . . . . ? C25 C26 C27 C28' -137.2(10) . . . . ? O27 C27 C28 C29 -133.4(4) . . . . ? C26 C27 C28 C29 107.3(4) . . . . ? C28' C27 C28 C29 7.8(12) . . . . ? C27 C28 C29 O12 -175.1(3) . . . . ? C12 O12 C29 C28 63.3(5) . . . . ? C29' O12 C29 C28 -17.9(13) . . . . ? O27 C27 C28' C29' 42(2) . . . . ? C28 C27 C28' C29' -12.8(11) . . . . ? C26 C27 C28' C29' -108.8(15) . . . . ? C27 C28' C29' O12 173.6(11) . . . . ? C29 O12 C29' C28' 10.9(10) . . . . ? C12 O12 C29' C28' -101.4(16) . . . . ? C25 O25 C35 O35 -3.4(4) . . . . ? C25 O25 C35 C36 175.9(2) . . . . ? C39 N38 C38 C3 176.5(2) . . . . ? C4 C3 C38 N38 86.9(3) . . . . ? C2 C3 C38 N38 -93.7(3) . . . . ? C38 N38 C39 C40 -68.8(3) . . . . ? N38 C39 C40 C41 126.5(4) . . . . ? C1B' Cl1B C1B Cl3B 55.5(8) . . . . ? C1B' Cl3B C1B Cl1B -61.8(9) . . . . ? C1B Cl1B C1B' Cl2B 172.7(12) . . . . ? C1B Cl1B C1B' Cl3B -62.7(10) . . . . ? C1B Cl3B C1B' Cl1B 53.2(11) . . . . ? C1B Cl3B C1B' Cl2B 179.5(14) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 O8 0.84 1.76 2.507(3) 146 . N38 H2N3 O15 0.90 2.08 2.893(3) 150 . O4 H4O O11 0.84 1.74 2.582(3) 178 . O23 H23O O21 0.84 2.04 2.752(3) 141 . O1C H1C O11 0.84 1.88 2.654(18) 153 . O1C' H1C' O11 0.84 1.82 2.65(3) 172 . O1D H1D O15 0.84 2.09 2.872(5) 155 . O1D' H1D' O1 0.84 2.26 3.056(15) 159 . N2 H1N2 O1A 0.90 1.99 2.850(4) 160 . O1A H1A O21 0.84 1.92 2.756(3) 173 . O21 H21O O1C 0.84 1.86 2.677(19) 163 2_646 O21 H21O O1C' 0.84 1.94 2.77(3) 169 2_646 N38 H1N3 O23 0.90 1.95 2.828(3) 164 2_656 N38 H2N3 O35 0.90 2.34 2.813(3) 112 2_656 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 74.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.481 _refine_diff_density_min -0.700 _refine_diff_density_rms 0.059