# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_tc83m _database_code_depnum_ccdc_archive 'CCDC 887928' #TrackingRef 'TC83m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H90 N2 O13' _chemical_formula_weight 759.10 _chemical_absolute_configuration syn loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.5730(5) _cell_length_b 15.2408(9) _cell_length_c 16.3095(10) _cell_angle_alpha 90.00 _cell_angle_beta 91.996(2) _cell_angle_gamma 90.00 _cell_volume 2378.1(2) _cell_formula_units_Z 2 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 4418 _cell_measurement_theta_min 2.67 _cell_measurement_theta_max 21.67 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.060 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9545 _exptl_absorpt_correction_T_max 0.9922 _exptl_absorpt_process_details 'SADABS (Bruker-AXS)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(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 'Bruker kappa APEX-II CCD Quazar' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 18337 _diffrn_reflns_av_R_equivalents 0.0338 _diffrn_reflns_av_sigmaI/netI 0.0539 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 5.13 _diffrn_reflns_theta_max 24.71 _reflns_number_total 8021 _reflns_number_gt 5571 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0970P)^2^+0.4179P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_number_reflns 8021 _refine_ls_number_parameters 534 _refine_ls_number_restraints 69 _refine_ls_R_factor_all 0.0953 _refine_ls_R_factor_gt 0.0625 _refine_ls_wR_factor_ref 0.1808 _refine_ls_wR_factor_gt 0.1579 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 1.1844(2) 0.02440(19) 0.27349(17) 0.0557(7) Uani 1 1 d . . . O2 O 1.2172(2) 0.0202(2) 0.13835(17) 0.0616(7) Uani 1 1 d . . . O3 O 0.9565(3) -0.0061(2) 0.09794(17) 0.0652(9) Uani 1 1 d . . . H3A H 1.025(5) 0.006(4) 0.080(3) 0.078 Uiso 1 1 d . . . O4 O 0.9578(3) 0.16280(18) 0.1868(2) 0.0618(8) Uani 1 1 d . . . H4A H 0.903(5) 0.178(4) 0.157(3) 0.074 Uiso 1 1 d . . . O5 O 0.6961(2) 0.1327(2) 0.15438(18) 0.0608(7) Uani 1 1 d . . . O6 O 0.6874(2) 0.01028(18) 0.22930(14) 0.0484(6) Uani 1 1 d . . . C1 C 1.1438(3) 0.0171(2) 0.2001(2) 0.0460(8) Uani 1 1 d . . . C2 C 0.9859(3) 0.0042(2) 0.1832(2) 0.0413(8) Uani 1 1 d . . . H2 H 0.9558 -0.0501 0.2120 0.050 Uiso 1 1 calc R . . C3 C 0.9065(3) 0.0820(2) 0.2170(2) 0.0384(7) Uani 1 1 d . . . H3 H 0.9214 0.0820 0.2780 0.046 Uiso 1 1 calc R . . C4 C 0.7497(3) 0.0743(3) 0.1981(2) 0.0413(8) Uani 1 1 d . . . N1 N 0.1901(3) 0.26355(18) 0.41784(17) 0.0423(7) Uani 1 1 d . . . C5 C 0.2945(4) 0.2483(3) 0.3511(2) 0.0503(9) Uani 1 1 d . . . H5A H 0.3281 0.1869 0.3557 0.060 Uiso 1 1 calc R . . H5B H 0.2444 0.2541 0.2973 0.060 Uiso 1 1 calc R . . C6 C 0.4196(4) 0.3073(3) 0.3513(3) 0.0612(10) Uani 1 1 d . . . H6A H 0.4668 0.3068 0.4063 0.073 Uiso 1 1 calc R . . H6B H 0.3895 0.3682 0.3390 0.073 Uiso 1 1 calc R . . C7 C 0.5206(5) 0.2766(4) 0.2874(3) 0.0803(15) Uani 1 1 d . . . H7A H 0.5492 0.2155 0.2999 0.096 Uiso 1 1 calc R . . H7B H 0.4721 0.2768 0.2328 0.096 Uiso 1 1 calc R . . C8 C 0.6499(6) 0.3339(4) 0.2844(3) 0.0976(19) Uani 1 1 d . . . H8A H 0.6225 0.3940 0.2701 0.146 Uiso 1 1 calc R . . H8B H 0.7121 0.3110 0.2429 0.146 Uiso 1 1 calc R . . H8C H 0.6989 0.3335 0.3382 0.146 Uiso 1 1 calc R . . C9 C 0.1439(4) 0.3589(3) 0.4203(3) 0.0557(10) Uani 1 1 d . . . H9A H 0.0798 0.3662 0.4662 0.067 Uiso 1 1 calc R . . H9B H 0.2272 0.3958 0.4327 0.067 Uiso 1 1 calc R . . C10 C 0.0723(5) 0.3930(3) 0.3435(3) 0.0799(14) Uani 1 1 d . . . H10A H -0.0168 0.3615 0.3323 0.096 Uiso 1 1 calc R . . H10B H 0.1326 0.3853 0.2959 0.096 Uiso 1 1 calc R . . C11 C 0.0436(9) 0.4964(6) 0.3599(5) 0.141(3) Uani 1 1 d . . . H11A H 0.0040 0.5019 0.4149 0.170 Uiso 1 1 calc R . . H11B H 0.1352 0.5267 0.3621 0.170 Uiso 1 1 calc R . . C12 C -0.0409(9) 0.5402(6) 0.3064(7) 0.167(4) Uani 1 1 d . . . H12A H -0.0021 0.5379 0.2517 0.251 Uiso 1 1 calc R . . H12B H -0.0484 0.6015 0.3239 0.251 Uiso 1 1 calc R . . H12C H -0.1338 0.5131 0.3048 0.251 Uiso 1 1 calc R . . C13 C 0.0673(3) 0.2030(3) 0.3994(2) 0.0480(9) Uani 1 1 d . . . H13A H 0.1025 0.1419 0.3975 0.058 Uiso 1 1 calc R . . H13B H 0.0277 0.2173 0.3441 0.058 Uiso 1 1 calc R . . C14 C -0.0500(4) 0.2068(3) 0.4601(3) 0.0604(11) Uani 1 1 d . . . H14A H -0.0820 0.2682 0.4662 0.073 Uiso 1 1 calc R . . H14B H -0.0155 0.1856 0.5145 0.073 Uiso 1 1 calc R . . C15 C -0.1713(4) 0.1496(4) 0.4288(3) 0.0736(13) Uani 1 1 d . . . H15A H -0.1995 0.1687 0.3726 0.088 Uiso 1 1 calc R . . H15B H -0.1386 0.0881 0.4254 0.088 Uiso 1 1 calc R . . C16 C -0.2979(5) 0.1527(4) 0.4819(3) 0.0902(17) Uani 1 1 d . . . H16A H -0.2731 0.1291 0.5363 0.135 Uiso 1 1 calc R . . H16B H -0.3733 0.1174 0.4565 0.135 Uiso 1 1 calc R . . H16C H -0.3293 0.2136 0.4872 0.135 Uiso 1 1 calc R . . C17 C 0.2562(4) 0.2454(3) 0.5019(2) 0.0501(9) Uani 1 1 d . . . H17A H 0.3372 0.2853 0.5098 0.060 Uiso 1 1 calc R . . H17B H 0.1875 0.2615 0.5434 0.060 Uiso 1 1 calc R . . C18 C 0.3055(4) 0.1536(3) 0.5202(3) 0.0625(11) Uani 1 1 d . . . H18A H 0.3698 0.1340 0.4776 0.075 Uiso 1 1 calc R . . H18B H 0.2247 0.1131 0.5199 0.075 Uiso 1 1 calc R . . C19 C 0.3806(5) 0.1522(4) 0.6041(3) 0.0894(16) Uani 1 1 d . . . H19A H 0.4601 0.1937 0.6029 0.107 Uiso 1 1 calc R . . H19B H 0.3154 0.1744 0.6451 0.107 Uiso 1 1 calc R . . C20 C 0.4344(7) 0.0664(5) 0.6326(4) 0.118(2) Uani 1 1 d . . . H20A H 0.3560 0.0261 0.6399 0.177 Uiso 1 1 calc R . . H20B H 0.4863 0.0738 0.6850 0.177 Uiso 1 1 calc R . . H20C H 0.4966 0.0422 0.5918 0.177 Uiso 1 1 calc R . . N2 N 0.5231(3) 0.84314(19) 0.0647(2) 0.0497(8) Uani 1 1 d . . . C21 C 0.4646(4) 0.8597(3) 0.1484(2) 0.0550(10) Uani 1 1 d . . . H21A H 0.5425 0.8777 0.1862 0.066 Uiso 1 1 calc R . . H21B H 0.3988 0.9097 0.1436 0.066 Uiso 1 1 calc R . . C22 C 0.3908(6) 0.7848(3) 0.1862(3) 0.0762(13) Uani 1 1 d . . . H22A H 0.4557 0.7345 0.1919 0.091 Uiso 1 1 calc R . . H22B H 0.3115 0.7667 0.1495 0.091 Uiso 1 1 calc R . . C23 C 0.3367(7) 0.8078(4) 0.2693(3) 0.0869(15) Uani 1 1 d . . . H23A H 0.4178 0.8167 0.3077 0.104 Uiso 1 1 calc R . . H23B H 0.2863 0.8644 0.2646 0.104 Uiso 1 1 calc R . . C24 C 0.2424(9) 0.7424(5) 0.3056(4) 0.123(2) Uani 1 1 d . . . H24A H 0.2833 0.6838 0.3011 0.185 Uiso 1 1 calc R . . H24B H 0.1515 0.7438 0.2761 0.185 Uiso 1 1 calc R . . H24C H 0.2301 0.7565 0.3635 0.185 Uiso 1 1 calc R . . C25 C 0.4094(4) 0.8116(3) 0.0043(2) 0.0547(10) Uani 1 1 d . . . H25A H 0.4532 0.7968 -0.0481 0.066 Uiso 1 1 calc R . . H25B H 0.3686 0.7570 0.0260 0.066 Uiso 1 1 calc R . . C26 C 0.2929(4) 0.8757(3) -0.0134(3) 0.0604(11) Uani 1 1 d . . . H26A H 0.3295 0.9274 -0.0425 0.072 Uiso 1 1 calc R . . H26B H 0.2542 0.8961 0.0388 0.072 Uiso 1 1 calc R . . C27 C 0.1785(4) 0.8323(3) -0.0659(3) 0.0657(12) Uani 1 1 d . . . H27A H 0.2206 0.8057 -0.1146 0.079 Uiso 1 1 calc R . . H27B H 0.1363 0.7844 -0.0340 0.079 Uiso 1 1 calc R . . C28 C 0.0662(6) 0.8943(4) -0.0937(4) 0.0955(17) Uani 1 1 d . . . H28A H 0.0145 0.9141 -0.0463 0.143 Uiso 1 1 calc R . . H28B H 0.0021 0.8646 -0.1328 0.143 Uiso 1 1 calc R . . H28C H 0.1082 0.9451 -0.1204 0.143 Uiso 1 1 calc R . . C29 C 0.5825(4) 0.9312(3) 0.0370(2) 0.0550(10) Uani 1 1 d . . . H29A H 0.5082 0.9761 0.0403 0.066 Uiso 1 1 calc R . . H29B H 0.6589 0.9484 0.0763 0.066 Uiso 1 1 calc R . . C30 C 0.6381(6) 0.9332(3) -0.0479(3) 0.0787(14) Uani 1 1 d . . . H30A H 0.5648 0.9129 -0.0877 0.094 Uiso 1 1 calc R . . H30B H 0.7187 0.8928 -0.0508 0.094 Uiso 1 1 calc R . . C31 C 0.6837(7) 1.0255(4) -0.0704(4) 0.1005(18) Uani 1 1 d . . . H31A H 0.6043 1.0661 -0.0631 0.121 Uiso 1 1 calc R . . H31B H 0.7605 1.0439 -0.0319 0.121 Uiso 1 1 calc R . . C32 C 0.7319(8) 1.0339(6) -0.1559(4) 0.132(3) Uani 1 1 d . . . H32A H 0.7951 0.9853 -0.1678 0.198 Uiso 1 1 calc R . . H32B H 0.7813 1.0898 -0.1619 0.198 Uiso 1 1 calc R . . H32C H 0.6509 1.0323 -0.1944 0.198 Uiso 1 1 calc R . . C33 C 0.6351(4) 0.7729(3) 0.0680(3) 0.0643(11) Uani 1 1 d . B . H33A H 0.5914 0.7169 0.0842 0.077 Uiso 1 1 calc R . . H33B H 0.6698 0.7649 0.0120 0.077 Uiso 1 1 calc R . . C34 C 0.7584(5) 0.7902(4) 0.1255(4) 0.0860(16) Uani 1 1 d D . . H34A H 0.7256 0.8132 0.1782 0.103 Uiso 1 1 calc R A 1 H34B H 0.8198 0.8349 0.1013 0.103 Uiso 1 1 calc R A 1 C35 C 0.8441(12) 0.7012(8) 0.1411(8) 0.113(3) Uani 0.612(12) 1 d PDU B 1 H35A H 0.9234 0.7130 0.1801 0.136 Uiso 0.612(12) 1 calc PR B 1 H35B H 0.7825 0.6577 0.1668 0.136 Uiso 0.612(12) 1 calc PR B 1 C36 C 0.8979(15) 0.6638(10) 0.0656(8) 0.144(4) Uani 0.612(12) 1 d PDU B 1 H36A H 0.8203 0.6393 0.0322 0.216 Uiso 0.612(12) 1 calc PR B 1 H36B H 0.9652 0.6172 0.0797 0.216 Uiso 0.612(12) 1 calc PR B 1 H36C H 0.9442 0.7098 0.0346 0.216 Uiso 0.612(12) 1 calc PR B 1 C35' C 0.8819(17) 0.7286(14) 0.1001(12) 0.105(4) Uani 0.388(12) 1 d PDU B 2 H35C H 0.8494 0.6669 0.1004 0.126 Uiso 0.388(12) 1 calc PR B 2 H35D H 0.9078 0.7431 0.0434 0.126 Uiso 0.388(12) 1 calc PR B 2 C36' C 1.004(2) 0.7367(18) 0.1540(15) 0.155(6) Uani 0.388(12) 1 d PDU B 2 H36D H 1.0504 0.7926 0.1435 0.233 Uiso 0.388(12) 1 calc PR B 2 H36E H 1.0681 0.6882 0.1439 0.233 Uiso 0.388(12) 1 calc PR B 2 H36F H 0.9754 0.7348 0.2111 0.233 Uiso 0.388(12) 1 calc PR B 2 O7 O 0.4569(2) 0.04109(19) 0.32606(17) 0.0548(7) Uani 1 1 d D . . H7C H 0.510(4) 0.040(3) 0.288(2) 0.066 Uiso 1 1 d D . . H7D H 0.380(3) 0.036(3) 0.304(2) 0.066 Uiso 1 1 d D . . O8 O 0.4231(3) 0.1383(2) 0.0952(2) 0.0638(8) Uani 1 1 d D . . H8D H 0.494(4) 0.130(4) 0.114(3) 0.077 Uiso 1 1 d D . . H8E H 0.373(4) 0.104(3) 0.108(3) 0.077 Uiso 1 1 d D . . O9 O 0.2093(3) 0.2541(2) 0.1471(2) 0.0698(8) Uani 1 1 d D . . H9D H 0.284(4) 0.223(3) 0.137(3) 0.084 Uiso 1 1 d D . . H9E H 0.156(5) 0.224(3) 0.180(3) 0.084 Uiso 1 1 d D . . O10 O 0.5281(5) 0.9264(2) 0.4481(2) 0.0910(11) Uani 1 1 d D . . H10D H 0.427(7) 0.912(4) 0.461(4) 0.109 Uiso 1 1 d . . . H10E H 0.516(6) 0.966(3) 0.417(3) 0.109 Uiso 1 1 d D . . O11 O 0.7801(4) 0.8999(2) 0.3515(2) 0.0840(11) Uani 1 1 d D . . H11C H 0.741(6) 0.927(4) 0.395(3) 0.101 Uiso 1 1 d D . . H11D H 0.743(6) 0.935(4) 0.310(3) 0.101 Uiso 1 1 d D . . O12 O 0.2596(5) 0.8936(4) 0.5046(3) 0.1235(16) Uani 1 1 d D . . H12D H 0.203(7) 0.916(5) 0.464(3) 0.148 Uiso 1 1 d D . . H12E H 0.205(7) 0.870(5) 0.546(4) 0.148 Uiso 1 1 d D . . O13 O 1.0560(4) 0.9503(3) 0.4049(2) 0.0997(14) Uani 1 1 d D . . H13D H 1.000(7) 0.914(4) 0.389(4) 0.120 Uiso 1 1 d D . . H13E H 1.088(7) 0.974(4) 0.366(3) 0.120 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0357(12) 0.0664(18) 0.0645(18) 0.0014(14) -0.0075(11) 0.0068(12) O2 0.0374(12) 0.0748(19) 0.0735(18) -0.0134(15) 0.0155(12) -0.0009(14) O3 0.0447(14) 0.100(2) 0.0512(17) -0.0233(15) 0.0033(12) -0.0046(16) O4 0.0352(13) 0.0462(16) 0.104(2) 0.0170(15) 0.0000(13) -0.0040(12) O5 0.0339(12) 0.0684(18) 0.0798(19) 0.0202(16) -0.0039(12) 0.0023(13) O6 0.0323(11) 0.0587(16) 0.0543(14) 0.0031(12) 0.0054(10) -0.0062(12) C1 0.0334(16) 0.042(2) 0.063(2) -0.0058(18) 0.0058(17) 0.0046(16) C2 0.0348(16) 0.045(2) 0.0439(19) -0.0057(15) 0.0007(13) 0.0008(16) C3 0.0269(15) 0.0418(19) 0.0464(18) 0.0025(16) -0.0009(13) 0.0032(15) C4 0.0328(16) 0.050(2) 0.0411(18) -0.0038(17) 0.0011(14) 0.0008(18) N1 0.0398(15) 0.0419(17) 0.0453(16) -0.0134(13) 0.0012(12) 0.0004(13) C5 0.0450(19) 0.061(2) 0.045(2) -0.0110(17) 0.0067(15) -0.0024(19) C6 0.052(2) 0.069(3) 0.063(2) -0.018(2) 0.0117(18) -0.008(2) C7 0.065(3) 0.112(4) 0.066(3) -0.033(3) 0.022(2) -0.027(3) C8 0.079(3) 0.127(5) 0.089(4) -0.030(3) 0.036(3) -0.040(3) C9 0.054(2) 0.047(2) 0.067(3) -0.0093(19) 0.0091(19) 0.0018(19) C10 0.064(3) 0.070(3) 0.106(4) 0.019(3) -0.006(3) 0.009(2) C11 0.147(6) 0.126(6) 0.151(7) 0.042(5) -0.001(5) 0.050(6) C12 0.133(6) 0.110(6) 0.260(12) 0.026(7) 0.004(7) 0.027(5) C13 0.0376(17) 0.056(2) 0.051(2) -0.0143(18) 0.0009(15) -0.0020(17) C14 0.0390(19) 0.068(3) 0.074(3) -0.018(2) 0.0080(18) -0.0040(19) C15 0.051(2) 0.087(3) 0.083(3) -0.029(3) 0.007(2) -0.014(2) C16 0.058(3) 0.125(5) 0.089(4) -0.025(3) 0.019(2) -0.021(3) C17 0.0421(18) 0.060(3) 0.048(2) -0.0101(17) 0.0024(15) -0.0020(18) C18 0.052(2) 0.062(3) 0.073(3) 0.007(2) -0.0030(19) -0.001(2) C19 0.073(3) 0.104(4) 0.089(4) 0.021(3) -0.023(3) -0.013(3) C20 0.105(4) 0.122(5) 0.125(5) 0.032(4) -0.021(4) -0.016(4) N2 0.0423(16) 0.0433(18) 0.063(2) -0.0184(14) -0.0063(14) 0.0014(14) C21 0.057(2) 0.055(2) 0.053(2) -0.0102(19) -0.0069(18) 0.004(2) C22 0.086(3) 0.065(3) 0.078(3) -0.014(2) 0.011(2) -0.014(2) C23 0.114(4) 0.077(3) 0.070(3) 0.003(3) 0.006(3) 0.009(3) C24 0.169(6) 0.107(5) 0.097(4) 0.009(4) 0.038(4) -0.009(5) C25 0.051(2) 0.054(2) 0.058(2) -0.0212(19) -0.0067(17) -0.0010(19) C26 0.056(2) 0.062(3) 0.061(3) -0.021(2) -0.0135(19) 0.001(2) C27 0.054(2) 0.079(3) 0.063(3) -0.020(2) -0.0017(19) -0.005(2) C28 0.082(3) 0.109(5) 0.093(4) -0.021(3) -0.030(3) 0.005(3) C29 0.052(2) 0.050(2) 0.062(2) -0.0055(18) -0.0096(18) -0.0040(19) C30 0.079(3) 0.074(3) 0.084(3) -0.006(3) 0.016(3) -0.016(3) C31 0.107(4) 0.110(5) 0.086(4) -0.002(3) 0.023(3) -0.025(4) C32 0.132(5) 0.144(7) 0.122(5) 0.041(5) 0.028(4) 0.025(5) C33 0.055(2) 0.056(3) 0.081(3) -0.016(2) -0.008(2) 0.014(2) C34 0.056(3) 0.086(4) 0.114(4) -0.020(3) -0.018(3) 0.023(3) C35 0.085(5) 0.131(6) 0.123(6) 0.005(5) -0.012(5) 0.023(5) C36 0.137(7) 0.144(8) 0.148(7) -0.011(6) -0.023(6) 0.050(6) C35' 0.098(6) 0.110(7) 0.106(7) -0.001(6) -0.009(6) 0.026(6) C36' 0.137(8) 0.166(9) 0.161(9) -0.003(8) -0.016(7) 0.002(8) O7 0.0358(13) 0.0715(19) 0.0571(17) -0.0043(13) -0.0011(11) 0.0032(13) O8 0.0400(14) 0.079(2) 0.072(2) 0.0230(16) -0.0032(14) 0.0009(15) O9 0.0499(16) 0.062(2) 0.097(2) 0.0155(17) 0.0029(15) -0.0039(15) O10 0.118(3) 0.084(3) 0.071(2) 0.0286(18) -0.002(2) 0.032(2) O11 0.076(2) 0.082(2) 0.095(3) 0.0363(19) 0.0196(18) 0.0198(18) O12 0.104(3) 0.155(4) 0.110(4) 0.049(3) -0.014(2) -0.030(3) O13 0.084(3) 0.140(4) 0.075(3) 0.024(2) 0.0023(19) 0.009(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.250(4) . ? O2 C1 1.250(4) . ? O3 C2 1.418(4) . ? O3 H3A 0.75(5) . ? O4 C3 1.420(4) . ? O4 H4A 0.74(5) . ? O5 C4 1.241(4) . ? O6 C4 1.259(4) . ? C1 C2 1.539(4) . ? C2 C3 1.522(5) . ? C2 H2 1.0000 . ? C3 C4 1.527(4) . ? C3 H3 1.0000 . ? N1 C17 1.515(5) . ? N1 C13 1.517(5) . ? N1 C9 1.520(5) . ? N1 C5 1.521(4) . ? C5 C6 1.498(5) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.520(6) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.517(7) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.501(6) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.622(10) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.346(10) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C14 1.524(5) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.527(6) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.515(6) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C18 1.504(6) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.524(6) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.475(9) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? N2 C21 1.514(5) . ? N2 C33 1.514(5) . ? N2 C25 1.521(5) . ? N2 C29 1.532(5) . ? C21 C22 1.487(6) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C23 1.509(7) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.481(9) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 C26 1.503(6) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 C27 1.519(5) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 C28 1.491(7) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 C30 1.501(6) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C30 C31 1.521(8) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C31 C32 1.491(8) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 C34 1.505(6) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 C35' 1.577(15) . ? C34 C35 1.602(11) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 C36 1.466(9) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? C35' C36' 1.440(17) . ? C35' H35C 0.9900 . ? C35' H35D 0.9900 . ? C36' H36D 0.9800 . ? C36' H36E 0.9800 . ? C36' H36F 0.9800 . ? O7 H7C 0.82(3) . ? O7 H7D 0.81(3) . ? O8 H8D 0.75(3) . ? O8 H8E 0.74(3) . ? O9 H9D 0.87(4) . ? O9 H9E 0.89(4) . ? O10 H10D 1.01(7) . ? O10 H10E 0.794(10) . ? O11 H11C 0.91(4) . ? O11 H11D 0.92(4) . ? O12 H12D 0.916(10) . ? O12 H12E 0.95(2) . ? O13 H13D 0.81(5) . ? O13 H13E 0.80(5) . ? 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 C2 O3 H3A 102(4) . . ? C3 O4 H4A 105(4) . . ? O2 C1 O1 127.1(3) . . ? O2 C1 C2 115.9(3) . . ? O1 C1 C2 117.0(3) . . ? O3 C2 C3 111.0(3) . . ? O3 C2 C1 110.5(3) . . ? C3 C2 C1 109.6(3) . . ? O3 C2 H2 108.6 . . ? C3 C2 H2 108.6 . . ? C1 C2 H2 108.6 . . ? O4 C3 C2 111.5(3) . . ? O4 C3 C4 110.2(3) . . ? C2 C3 C4 111.5(3) . . ? O4 C3 H3 107.8 . . ? C2 C3 H3 107.8 . . ? C4 C3 H3 107.8 . . ? O5 C4 O6 126.6(3) . . ? O5 C4 C3 116.4(3) . . ? O6 C4 C3 117.0(3) . . ? C17 N1 C13 111.4(3) . . ? C17 N1 C9 105.2(3) . . ? C13 N1 C9 111.3(3) . . ? C17 N1 C5 110.8(3) . . ? C13 N1 C5 106.8(2) . . ? C9 N1 C5 111.4(3) . . ? C6 C5 N1 116.8(3) . . ? C6 C5 H5A 108.1 . . ? N1 C5 H5A 108.1 . . ? C6 C5 H5B 108.1 . . ? N1 C5 H5B 108.1 . . ? H5A C5 H5B 107.3 . . ? C5 C6 C7 109.9(3) . . ? C5 C6 H6A 109.7 . . ? C7 C6 H6A 109.7 . . ? C5 C6 H6B 109.7 . . ? C7 C6 H6B 109.7 . . ? H6A C6 H6B 108.2 . . ? C8 C7 C6 112.6(4) . . ? C8 C7 H7A 109.1 . . ? C6 C7 H7A 109.1 . . ? C8 C7 H7B 109.1 . . ? C6 C7 H7B 109.1 . . ? H7A C7 H7B 107.8 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 N1 115.7(3) . . ? C10 C9 H9A 108.4 . . ? N1 C9 H9A 108.4 . . ? C10 C9 H9B 108.4 . . ? N1 C9 H9B 108.4 . . ? H9A C9 H9B 107.4 . . ? C9 C10 C11 105.9(5) . . ? C9 C10 H10A 110.6 . . ? C11 C10 H10A 110.6 . . ? C9 C10 H10B 110.6 . . ? C11 C10 H10B 110.6 . . ? H10A C10 H10B 108.7 . . ? C12 C11 C10 118.4(8) . . ? C12 C11 H11A 107.7 . . ? C10 C11 H11A 107.7 . . ? C12 C11 H11B 107.7 . . ? C10 C11 H11B 107.7 . . ? H11A C11 H11B 107.1 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N1 C13 C14 115.5(3) . . ? N1 C13 H13A 108.4 . . ? C14 C13 H13A 108.4 . . ? N1 C13 H13B 108.4 . . ? C14 C13 H13B 108.4 . . ? H13A C13 H13B 107.5 . . ? C13 C14 C15 109.2(3) . . ? C13 C14 H14A 109.8 . . ? C15 C14 H14A 109.8 . . ? C13 C14 H14B 109.8 . . ? C15 C14 H14B 109.8 . . ? H14A C14 H14B 108.3 . . ? C16 C15 C14 113.9(4) . . ? C16 C15 H15A 108.8 . . ? C14 C15 H15A 108.8 . . ? C16 C15 H15B 108.8 . . ? C14 C15 H15B 108.8 . . ? H15A C15 H15B 107.7 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C18 C17 N1 117.9(3) . . ? C18 C17 H17A 107.8 . . ? N1 C17 H17A 107.8 . . ? C18 C17 H17B 107.8 . . ? N1 C17 H17B 107.8 . . ? H17A C17 H17B 107.2 . . ? C17 C18 C19 109.1(4) . . ? C17 C18 H18A 109.9 . . ? C19 C18 H18A 109.9 . . ? C17 C18 H18B 109.9 . . ? C19 C18 H18B 109.9 . . ? H18A C18 H18B 108.3 . . ? C20 C19 C18 116.4(5) . . ? C20 C19 H19A 108.2 . . ? C18 C19 H19A 108.2 . . ? C20 C19 H19B 108.2 . . ? C18 C19 H19B 108.2 . . ? H19A C19 H19B 107.4 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C21 N2 C33 111.7(3) . . ? C21 N2 C25 111.0(3) . . ? C33 N2 C25 106.8(3) . . ? C21 N2 C29 105.8(3) . . ? C33 N2 C29 111.1(3) . . ? C25 N2 C29 110.5(3) . . ? C22 C21 N2 116.2(3) . . ? C22 C21 H21A 108.2 . . ? N2 C21 H21A 108.2 . . ? C22 C21 H21B 108.2 . . ? N2 C21 H21B 108.2 . . ? H21A C21 H21B 107.4 . . ? C21 C22 C23 112.2(4) . . ? C21 C22 H22A 109.2 . . ? C23 C22 H22A 109.2 . . ? C21 C22 H22B 109.2 . . ? C23 C22 H22B 109.2 . . ? H22A C22 H22B 107.9 . . ? C24 C23 C22 115.8(5) . . ? C24 C23 H23A 108.3 . . ? C22 C23 H23A 108.3 . . ? C24 C23 H23B 108.3 . . ? C22 C23 H23B 108.3 . . ? H23A C23 H23B 107.4 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C26 C25 N2 115.3(3) . . ? C26 C25 H25A 108.4 . . ? N2 C25 H25A 108.4 . . ? C26 C25 H25B 108.4 . . ? N2 C25 H25B 108.4 . . ? H25A C25 H25B 107.5 . . ? C25 C26 C27 109.9(3) . . ? C25 C26 H26A 109.7 . . ? C27 C26 H26A 109.7 . . ? C25 C26 H26B 109.7 . . ? C27 C26 H26B 109.7 . . ? H26A C26 H26B 108.2 . . ? C28 C27 C26 113.2(4) . . ? C28 C27 H27A 108.9 . . ? C26 C27 H27A 108.9 . . ? C28 C27 H27B 108.9 . . ? C26 C27 H27B 108.9 . . ? H27A C27 H27B 107.8 . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C30 C29 N2 115.9(3) . . ? C30 C29 H29A 108.3 . . ? N2 C29 H29A 108.3 . . ? C30 C29 H29B 108.3 . . ? N2 C29 H29B 108.3 . . ? H29A C29 H29B 107.4 . . ? C29 C30 C31 110.8(4) . . ? C29 C30 H30A 109.5 . . ? C31 C30 H30A 109.5 . . ? C29 C30 H30B 109.5 . . ? C31 C30 H30B 109.5 . . ? H30A C30 H30B 108.1 . . ? C32 C31 C30 114.0(6) . . ? C32 C31 H31A 108.8 . . ? C30 C31 H31A 108.8 . . ? C32 C31 H31B 108.8 . . ? C30 C31 H31B 108.8 . . ? H31A C31 H31B 107.7 . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C34 C33 N2 115.9(3) . . ? C34 C33 H33A 108.3 . . ? N2 C33 H33A 108.3 . . ? C34 C33 H33B 108.3 . . ? N2 C33 H33B 108.3 . . ? H33A C33 H33B 107.4 . . ? C33 C34 C35' 108.1(7) . . ? C33 C34 C35 109.7(6) . . ? C33 C34 H34A 109.7 . . ? C35' C34 H34A 134.6 . . ? C35 C34 H34A 109.7 . . ? C33 C34 H34B 109.7 . . ? C35' C34 H34B 81.0 . . ? C35 C34 H34B 109.7 . . ? H34A C34 H34B 108.2 . . ? C36 C35 C34 112.9(9) . . ? C36 C35 H35A 109.0 . . ? C34 C35 H35A 109.0 . . ? C36 C35 H35B 109.0 . . ? C34 C35 H35B 109.0 . . ? H35A C35 H35B 107.8 . . ? 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 . . ? C36' C35' C34 112.8(14) . . ? C36' C35' H35C 109.0 . . ? C34 C35' H35C 109.0 . . ? C36' C35' H35D 109.0 . . ? C34 C35' H35D 109.0 . . ? H35C C35' H35D 107.8 . . ? C35' C36' H36D 109.5 . . ? C35' C36' H36E 109.5 . . ? H36D C36' H36E 109.5 . . ? C35' C36' H36F 109.5 . . ? H36D C36' H36F 109.5 . . ? H36E C36' H36F 109.5 . . ? H7C O7 H7D 104(4) . . ? H8D O8 H8E 111(6) . . ? H9D O9 H9E 109(5) . . ? H10D O10 H10E 99(6) . . ? H11C O11 H11D 98(5) . . ? H12D O12 H12E 110(7) . . ? H13D O13 H13E 109(8) . . ? 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 O3 H3A O2 0.75(5) 2.05(5) 2.590(4) 129(5) . O4 H4A O5 0.74(5) 2.10(5) 2.584(3) 124(5) . O7 H7C O6 0.82(3) 2.03(3) 2.797(3) 156(4) . O7 H7D O1 0.81(3) 1.93(3) 2.729(3) 169(4) 1_455 O8 H8D O5 0.75(3) 2.02(3) 2.755(4) 168(6) . O8 H8E O2 0.74(3) 2.04(3) 2.778(4) 174(5) 1_455 O9 H9D O8 0.87(4) 2.00(4) 2.854(5) 166(5) . O9 H9E O4 0.89(4) 2.11(4) 2.874(4) 143(4) 1_455 O10 H10D O12 1.01(7) 1.80(7) 2.805(7) 168(5) . O10 H10E O7 0.794(10) 1.940(18) 2.719(4) 166(6) 1_565 O11 H11C O10 0.91(4) 2.24(5) 2.954(5) 135(5) . O11 H11D O6 0.92(4) 1.81(4) 2.733(4) 174(5) 1_565 O12 H12D O13 0.916(10) 1.75(3) 2.641(6) 163(8) 1_455 O13 H13D O11 0.81(5) 2.18(6) 2.856(6) 142(7) . O13 H13E O1 0.80(5) 1.95(5) 2.750(5) 173(7) 1_565 _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 24.71 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.388 _refine_diff_density_min -0.224 _refine_diff_density_rms 0.040