data_global _journal_name_full 'Soft Matter' _journal_coden_cambridge 0777 _journal_year 2010 _journal_volume 6 _journal_page_first 0 _publ_contact_author_name 'John Bacsa' _publ_contact_author_email John.Bacsa@liverpool.ac.uk loop_ _publ_author_name 'Dave J. Adams' 'Kyle Morris' 'Lin Chen.' 'Louise Serpell' 'John Bacsa' 'Graeme M. Day' data_2NaG _database_code_depnum_ccdc_archive 'CCDC 764714' #TrackingRef 'NEEDLEM.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (2Z)-[(2-{[(naphthalen-1-yloxy)acetyl]amino}propanoyl) imino]ethanoic acid ; _chemical_name_common 2NaG _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H18 N2 O5' _chemical_formula_weight 330.33 _chemical_absolute_configuration rm 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 P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.872(5) _cell_length_b 4.921(3) _cell_length_c 16.859(9) _cell_angle_alpha 90.00 _cell_angle_beta 96.518(9) _cell_angle_gamma 90.00 _cell_volume 813.8(8) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 747 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 23.54 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.348 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 348 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9515 _exptl_absorpt_correction_T_max 0.9950 _exptl_absorpt_process_details 'SADABS V2008-1 (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 D8 diffractometer with APEX detector' _diffrn_measurement_method '\w scans with a narrow frame width' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3491 _diffrn_reflns_av_R_equivalents 0.1255 _diffrn_reflns_av_sigmaI/netI 0.3184 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 23.58 _reflns_number_total 2210 _reflns_number_gt 1143 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART v.5.632 (Bruker, 2005)' _computing_cell_refinement 'SAINT v6.45a (Bruker, 2005)' _computing_data_reduction 'SAINT v6.45a (Bruker, 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; The crystals were very thin needles, and the data were very weak. There was no observable diffraction above 24 degrees, and the maximum theta angle that data were collected at set was 23.6 degrees. 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^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1(4) _refine_ls_number_reflns 2210 _refine_ls_number_parameters 221 _refine_ls_number_restraints 225 _refine_ls_R_factor_all 0.1748 _refine_ls_R_factor_gt 0.0900 _refine_ls_wR_factor_ref 0.2337 _refine_ls_wR_factor_gt 0.1911 _refine_ls_goodness_of_fit_ref 0.865 _refine_ls_restrained_S_all 0.822 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags O1 O Uani 0.7137(5) 0.4937(13) 0.7844(3) 1.000 0.026(2) . . O2 O Uani 0.6906(5) 0.9017(14) 0.6085(3) 1.000 0.0263(19) . . O3 O Uani 1.0401(5) 0.6546(14) 0.6220(3) 1.000 0.026(2) . . O4 O Uani 1.3517(5) 0.9244(18) 0.6485(3) 1.000 0.044(3) . . O5 O Uani 1.4292(5) 0.9048(15) 0.5282(3) 1.000 0.030(2) . . N1 N Uani 0.8521(6) 0.8535(15) 0.7149(4) 1.000 0.022(3) . . N2 N Uani 1.0931(6) 1.0803(16) 0.5803(4) 1.000 0.024(3) . . C1 C Uani 0.6494(8) 0.293(2) 0.8266(5) 1.000 0.024(3) . . C2 C Uani 0.5333(8) 0.158(2) 0.7935(5) 1.000 0.024(3) . . C3 C Uani 0.4793(8) -0.047(2) 0.8394(5) 1.000 0.033(3) . . C4 C Uani 0.5403(8) -0.119(2) 0.9126(5) 1.000 0.031(3) . . C5 C Uani 0.6580(8) 0.0210(19) 0.9485(5) 1.000 0.022(3) . . C6 C Uani 0.7184(8) -0.031(2) 1.0276(5) 1.000 0.027(3) . . C7 C Uani 0.8264(8) 0.119(2) 1.0607(5) 1.000 0.024(3) . . C8 C Uani 0.8798(9) 0.338(2) 1.0185(5) 1.000 0.031(3) . . C9 C Uani 0.8268(7) 0.385(2) 0.9412(5) 1.000 0.025(3) . . C10 C Uani 0.7127(8) 0.241(2) 0.9043(5) 1.000 0.022(3) . . C11 C Uani 0.6493(8) 0.573(2) 0.7058(5) 1.000 0.026(2) . . C12 C Uani 0.7319(8) 0.791(2) 0.6733(5) 1.000 0.026(2) . . C13 C Uani 0.9492(7) 1.0430(18) 0.6883(5) 1.000 0.018(3) . . C14 C Uani 1.0472(8) 1.142(2) 0.7598(5) 1.000 0.027(3) . . C15 C Uani 1.0312(7) 0.907(2) 0.6263(5) 1.000 0.017(3) . . C16 C Uani 1.1920(7) 0.983(2) 0.5294(4) 1.000 0.025(3) . . C17 C Uani 1.3323(8) 0.937(2) 0.5767(5) 1.000 0.032(3) . . H1 H Uiso 0.865(6) 0.751(11) 0.765(2) 1.000 0.050(18) . . H2 H Uiso 0.49130 0.20240 0.74160 1.000 0.0290 calc R H2N H Uiso 1.087(9) 1.276(4) 0.590(5) 1.000 0.05(3) . . H3 H Uiso 0.39800 -0.13800 0.81850 1.000 0.0390 calc R H4 H Uiso 0.50390 -0.26450 0.94040 1.000 0.0370 calc R H5 H Uiso 1.50470 0.87980 0.55550 1.000 0.0360 calc R H6 H Uiso 0.68310 -0.17170 1.05780 1.000 0.0320 calc R H7 H Uiso 0.86710 0.07650 1.11300 1.000 0.0290 calc R H8 H Uiso 0.95080 0.44900 1.04370 1.000 0.0380 calc R H9 H Uiso 0.86800 0.51990 0.91140 1.000 0.0290 calc R H11A H Uiso 0.64310 0.41440 0.66960 1.000 0.0320 calc R H11B H Uiso 0.55580 0.64020 0.71000 1.000 0.0320 calc R H13 H Uiso 0.89880 1.20280 0.66300 1.000 0.0210 calc R H14A H Uiso 0.99460 1.21810 0.80050 1.000 0.0400 calc R H14B H Uiso 1.10760 1.28190 0.74210 1.000 0.0400 calc R H14C H Uiso 1.10190 0.98860 0.78260 1.000 0.0400 calc R H16A H Uiso 1.20060 1.11770 0.48660 1.000 0.0300 calc R H16B H Uiso 1.15930 0.81050 0.50390 1.000 0.0300 calc R loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.016(3) 0.039(5) 0.021(3) 0.003(3) -0.003(2) 0.001(3) O2 0.023(3) 0.031(4) 0.025(3) 0.004(3) 0.003(3) 0.010(3) O3 0.022(3) 0.023(5) 0.033(4) -0.001(3) 0.008(3) -0.004(3) O4 0.021(3) 0.086(6) 0.022(4) -0.004(4) -0.005(3) 0.010(4) O5 0.011(3) 0.053(5) 0.025(3) -0.004(3) 0.000(3) 0.008(3) N1 0.014(4) 0.030(6) 0.023(4) 0.008(4) 0.007(3) -0.001(4) N2 0.010(4) 0.037(7) 0.026(4) 0.002(4) 0.003(3) -0.002(4) C1 0.017(4) 0.033(6) 0.022(4) 0.010(4) 0.009(3) 0.001(4) C2 0.017(4) 0.037(6) 0.020(5) -0.004(4) 0.008(4) 0.006(4) C3 0.022(5) 0.047(7) 0.030(5) -0.004(5) 0.009(4) -0.002(5) C4 0.019(4) 0.039(7) 0.036(5) 0.005(5) 0.006(4) 0.002(4) C5 0.019(4) 0.026(6) 0.022(4) -0.008(4) 0.009(3) 0.004(4) C6 0.018(4) 0.024(6) 0.040(5) 0.008(4) 0.008(4) 0.007(4) C7 0.028(5) 0.020(6) 0.024(5) 0.003(4) 0.001(4) 0.014(4) C8 0.031(5) 0.022(7) 0.037(5) 0.007(4) -0.013(4) 0.002(4) C9 0.022(4) 0.029(6) 0.025(4) 0.003(4) 0.011(3) 0.006(4) C10 0.017(4) 0.023(6) 0.026(4) -0.002(4) -0.001(3) 0.014(4) C11 0.014(3) 0.032(5) 0.034(4) -0.008(3) 0.007(3) -0.005(3) C12 0.014(3) 0.032(5) 0.034(4) -0.008(3) 0.007(3) -0.005(3) C13 0.010(4) 0.020(6) 0.024(5) 0.005(4) 0.000(3) -0.008(4) C14 0.031(5) 0.026(6) 0.023(5) -0.002(4) 0.002(4) -0.012(5) C15 0.013(4) 0.020(7) 0.016(4) 0.006(4) -0.007(3) 0.000(5) C16 0.015(4) 0.044(8) 0.017(4) 0.003(5) 0.007(3) -0.010(5) C17 0.027(5) 0.047(7) 0.020(5) 0.003(5) -0.003(4) -0.014(5) _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.410(11) . . yes O1 C11 1.456(10) . . yes O2 C12 1.247(10) . . yes O3 C15 1.248(12) . . yes O4 C17 1.206(10) . . yes O5 C17 1.337(10) . . yes O5 H5 0.8400 . . no N1 C12 1.344(10) . . yes N1 C13 1.445(10) . . yes N2 C15 1.345(11) . . yes N2 C16 1.452(10) . . yes N1 H1 0.98(4) . . no N2 H2N 0.98(3) . . no C1 C10 1.409(12) . . no C1 C2 1.386(12) . . no C2 C3 1.412(13) . . no C3 C4 1.357(12) . . no C4 C5 1.425(12) . . no C5 C6 1.421(12) . . no C5 C10 1.453(13) . . no C6 C7 1.363(12) . . no C7 C8 1.425(13) . . no C8 C9 1.368(12) . . no C9 C10 1.414(12) . . no C11 C12 1.489(13) . . no C13 C14 1.537(12) . . no C13 C15 1.545(11) . . no C16 C17 1.535(11) . . no C2 H2 0.9500 . . no C3 H3 0.9500 . . no C4 H4 0.9500 . . no C6 H6 0.9500 . . no C7 H7 0.9500 . . no C8 H8 0.9500 . . no C9 H9 0.9500 . . no C11 H11A 0.9900 . . no C11 H11B 0.9900 . . no C13 H13 1.0000 . . no C14 H14A 0.9800 . . no C14 H14B 0.9800 . . no C14 H14C 0.9800 . . no C16 H16A 0.9900 . . no C16 H16B 0.9900 . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C11 118.2(6) . . . yes C17 O5 H5 110.00 . . . no C12 N1 C13 124.3(7) . . . yes C15 N2 C16 120.8(8) . . . yes C13 N1 H1 125(3) . . . no C12 N1 H1 111(3) . . . no C16 N2 H2N 119(5) . . . no C15 N2 H2N 119(5) . . . no C2 C1 C10 123.1(8) . . . no O1 C1 C2 122.1(7) . . . yes O1 C1 C10 114.8(7) . . . yes C1 C2 C3 117.9(8) . . . no C2 C3 C4 121.9(8) . . . no C3 C4 C5 121.1(8) . . . no C4 C5 C10 118.4(8) . . . no C4 C5 C6 123.1(8) . . . no C6 C5 C10 118.4(8) . . . no C5 C6 C7 120.8(8) . . . no C6 C7 C8 121.4(8) . . . no C7 C8 C9 118.7(8) . . . no C8 C9 C10 122.3(8) . . . no C1 C10 C9 124.4(8) . . . no C1 C10 C5 117.4(8) . . . no C5 C10 C9 118.2(8) . . . no O1 C11 C12 109.1(7) . . . yes O2 C12 N1 122.6(8) . . . yes N1 C12 C11 117.4(7) . . . yes O2 C12 C11 119.9(7) . . . yes N1 C13 C15 110.3(7) . . . yes C14 C13 C15 109.7(6) . . . no N1 C13 C14 110.0(7) . . . yes O3 C15 C13 121.1(7) . . . yes N2 C15 C13 115.0(8) . . . yes O3 C15 N2 123.9(7) . . . yes N2 C16 C17 111.7(6) . . . yes O4 C17 C16 124.1(7) . . . yes O5 C17 C16 111.5(6) . . . yes O4 C17 O5 124.4(7) . . . yes C1 C2 H2 121.00 . . . no C3 C2 H2 121.00 . . . no C2 C3 H3 119.00 . . . no C4 C3 H3 119.00 . . . no C3 C4 H4 120.00 . . . no C5 C4 H4 119.00 . . . no C5 C6 H6 120.00 . . . no C7 C6 H6 120.00 . . . no C6 C7 H7 119.00 . . . no C8 C7 H7 119.00 . . . no C7 C8 H8 120.00 . . . no C9 C8 H8 121.00 . . . no C8 C9 H9 119.00 . . . no C10 C9 H9 119.00 . . . no O1 C11 H11A 110.00 . . . no O1 C11 H11B 110.00 . . . no C12 C11 H11A 110.00 . . . no C12 C11 H11B 110.00 . . . no H11A C11 H11B 108.00 . . . no N1 C13 H13 109.00 . . . no C14 C13 H13 109.00 . . . no C15 C13 H13 109.00 . . . no C13 C14 H14A 109.00 . . . no C13 C14 H14B 110.00 . . . no C13 C14 H14C 109.00 . . . no H14A C14 H14B 110.00 . . . no H14A C14 H14C 109.00 . . . no H14B C14 H14C 109.00 . . . no N2 C16 H16A 109.00 . . . no N2 C16 H16B 109.00 . . . no C17 C16 H16A 109.00 . . . no C17 C16 H16B 109.00 . . . no H16A C16 H16B 108.00 . . . no 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 _geom_hbond_publ_flag N1 H1 O1 0.98(4) 2.01(6) 2.596(9) 116(4) . yes N2 H2N O3 0.98(3) 2.01(4) 2.973(10) 168(7) 1_565 yes O5 H5 O2 0.8400 1.9500 2.775(7) 167.00 1_655 yes C2 H2 O4 0.9500 2.4000 3.085(10) 129.00 1_445 yes C11 H11B O4 0.9900 2.5700 3.451(11) 148.00 1_455 yes C16 H16A O2 0.9900 2.4600 3.407(10) 159.00 2_756 yes _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 23.58 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.231 _refine_diff_density_min -0.246 _refine_diff_density_rms 0.063 # Attachment 'da20090m.cif' data_da20090m _database_code_depnum_ccdc_archive 'CCDC 764715' #TrackingRef 'da20090m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-[({[(naphthalen-1-yloxy)acetyl]amino}acetyl)amino]propanoic acid ; _chemical_name_common DA201109 _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H18 N2 O5' _chemical_formula_weight 330.33 _chemical_absolute_configuration rm 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 P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 9.9170(10) _cell_length_b 11.1123(11) _cell_length_c 28.247(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3112.8(6) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5469 _cell_measurement_theta_min 2.18 _cell_measurement_theta_max 27.06 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.410 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1392 _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9692 _exptl_absorpt_correction_T_max 0.9896 _exptl_absorpt_process_details 'SADABS V2008-1 (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 D8 diffractometer with APEX detector' _diffrn_measurement_method '\w scans with a narrow frame width' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17876 _diffrn_reflns_av_R_equivalents 0.0275 _diffrn_reflns_av_sigmaI/netI 0.0369 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.44 _diffrn_reflns_theta_max 27.10 _reflns_number_total 6726 _reflns_number_gt 6106 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART v.5.632 (Bruker, 2005)' _computing_cell_refinement 'SAINT v6.45a (Bruker, 2005)' _computing_data_reduction 'SAINT v6.45a (Bruker, 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0375P)^2^+0.1944P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.2(6) _refine_ls_number_reflns 6726 _refine_ls_number_parameters 498 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0402 _refine_ls_R_factor_gt 0.0346 _refine_ls_wR_factor_ref 0.0767 _refine_ls_wR_factor_gt 0.0740 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags O1 O Uani 1.00050(12) 0.19007(11) 0.40521(4) 1.000 0.0235(3) . . O2 O Uani 1.03173(12) 0.31620(10) 0.46578(4) 1.000 0.0261(4) . . O3 O Uani 0.65518(11) 0.36804(10) 0.45586(4) 1.000 0.0222(3) . . O4 O Uani 0.24560(11) 0.25317(9) 0.37633(4) 1.000 0.0198(3) . . O5 O Uani 0.32013(11) 0.55791(9) 0.40254(4) 1.000 0.0191(3) . . N1 N Uani 0.72759(13) 0.18015(12) 0.43713(5) 1.000 0.0174(4) . . N2 N Uani 0.43098(14) 0.34788(12) 0.40359(5) 1.000 0.0172(4) . . C1 C Uani 0.96795(16) 0.23803(13) 0.44677(5) 1.000 0.0168(4) . . C2 C Uani 0.84321(16) 0.17960(14) 0.46842(5) 1.000 0.0180(4) . . C3 C Uani 0.63890(16) 0.27076(14) 0.43617(5) 1.000 0.0170(4) . . C4 C Uani 0.51059(16) 0.24004(13) 0.40956(6) 1.000 0.0175(4) . . C5 C Uani 0.30538(16) 0.34665(14) 0.38823(5) 1.000 0.0168(4) . . C6 C Uani 0.23215(17) 0.46524(13) 0.38670(6) 1.000 0.0188(5) . . C7 C Uani 0.26423(16) 0.66905(14) 0.41100(5) 1.000 0.0173(4) . . C8 C Uani 0.34865(17) 0.74996(13) 0.43663(5) 1.000 0.0172(4) . . C9 C Uani 0.29668(17) 0.86588(14) 0.44755(6) 1.000 0.0202(5) . . C10 C Uani 0.16609(18) 0.89795(15) 0.43185(6) 1.000 0.0246(5) . . C11 C Uani 0.08937(18) 0.81798(15) 0.40731(6) 1.000 0.0250(5) . . C12 C Uani 0.13767(17) 0.70152(15) 0.39668(6) 1.000 0.0219(5) . . C13 C Uani 0.37815(18) 0.94622(15) 0.47416(6) 1.000 0.0259(5) . . C14 C Uani 0.50472(19) 0.91455(15) 0.48799(6) 1.000 0.0271(5) . . C15 C Uani 0.55703(18) 0.80002(14) 0.47664(6) 1.000 0.0235(5) . . C16 C Uani 0.48058(17) 0.71916(14) 0.45176(5) 1.000 0.0198(5) . . C17 C Uani 0.87484(17) 0.04954(14) 0.48214(6) 1.000 0.0215(5) . . O6 O Uani -0.09928(13) 1.16927(11) 0.22799(4) 1.000 0.0275(4) . . O7 O Uani 0.07776(13) 1.26538(10) 0.25942(5) 1.000 0.0332(4) . . O8 O Uani 0.22904(11) 0.86591(9) 0.29835(4) 1.000 0.0203(3) . . O9 O Uani 0.64656(12) 1.00082(10) 0.36755(4) 1.000 0.0230(3) . . O10 O Uani 0.59976(11) 0.69364(9) 0.33890(4) 1.000 0.0201(3) . . N3 N Uani 0.17808(14) 1.06476(12) 0.29798(5) 1.000 0.0188(4) . . N4 N Uani 0.46727(14) 0.89738(12) 0.33985(5) 1.000 0.0173(4) . . C18 C Uani 0.01360(17) 1.17523(15) 0.25318(6) 1.000 0.0211(5) . . C19 C Uani 0.04908(16) 1.05360(14) 0.27435(6) 1.000 0.0186(5) . . C20 C Uani 0.25519(17) 0.97082(13) 0.30902(5) 1.000 0.0166(4) . . C21 C Uani 0.38180(16) 1.00168(14) 0.33622(6) 1.000 0.0173(4) . . C22 C Uani 0.59419(16) 0.90615(14) 0.35483(5) 1.000 0.0166(4) . . C23 C Uani 0.67721(16) 0.79245(13) 0.35543(6) 1.000 0.0189(5) . . C24 C Uani 0.66348(17) 0.58404(14) 0.33630(5) 1.000 0.0192(5) . . C25 C Uani 0.58737(17) 0.49257(14) 0.31332(5) 1.000 0.0183(4) . . C26 C Uani 0.64525(18) 0.37602(14) 0.30971(5) 1.000 0.0210(5) . . C27 C Uani 0.77507(18) 0.35472(15) 0.32896(6) 1.000 0.0242(5) . . C28 C Uani 0.84378(18) 0.44470(15) 0.35068(6) 1.000 0.0273(5) . . C29 C Uani 0.78824(17) 0.56160(15) 0.35467(6) 1.000 0.0234(5) . . C30 C Uani 0.57007(19) 0.28368(15) 0.28779(6) 1.000 0.0241(5) . . C31 C Uani 0.44259(19) 0.30467(15) 0.27128(6) 1.000 0.0252(5) . . C32 C Uani 0.38508(18) 0.42001(15) 0.27496(6) 1.000 0.0237(5) . . C33 C Uani 0.45627(17) 0.51228(14) 0.29503(5) 1.000 0.0196(5) . . C34 C Uani -0.06154(17) 1.01141(15) 0.30800(6) 1.000 0.0208(5) . . H1 H Uiso 1.078(3) 0.2204(19) 0.3949(7) 1.000 0.030(7) . . H1N H Uiso 0.711(2) 0.1157(17) 0.4209(6) 1.000 0.028(5) . . H2 H Uiso 0.81890 0.22480 0.49780 1.000 0.008(4) calc R H2N H Uiso 0.4669(19) 0.4147(17) 0.4108(6) 1.000 0.023(5) . . H4A H Uiso 0.53330 0.20570 0.37820 1.000 0.019(4) calc R H4B H Uiso 0.45830 0.17930 0.42750 1.000 0.016(4) calc R H6A H Uiso 0.20220 0.48230 0.35390 1.000 0.015(4) calc R H6B H Uiso 0.15140 0.46180 0.40730 1.000 0.015(4) calc R H10 H Uiso 0.13170 0.97600 0.43850 1.000 0.023(5) calc R H11 H Uiso 0.00170 0.84090 0.39710 1.000 0.020(5) calc R H12 H Uiso 0.08280 0.64630 0.37970 1.000 0.015(4) calc R H13 H Uiso 0.34380 1.02320 0.48240 1.000 0.030(5) calc R H14 H Uiso 0.55820 0.96990 0.50540 1.000 0.026(5) calc R H15 H Uiso 0.64570 0.77890 0.48630 1.000 0.029(5) calc R H16 H Uiso 0.51620 0.64190 0.44460 1.000 0.025(5) calc R H17A H Uiso 0.80220 0.01800 0.50210 1.000 0.031(5) calc R H17B H Uiso 0.96010 0.04690 0.49960 1.000 0.030(5) calc R H17C H Uiso 0.88240 0.00040 0.45350 1.000 0.023(5) calc R H3N H Uiso 0.2025(19) 1.1349(17) 0.3084(6) 1.000 0.023(5) . . H4N H Uiso 0.434(2) 0.8286(17) 0.3307(6) 1.000 0.027(5) . . H6 H Uiso -0.126(3) 1.247(2) 0.2186(8) 1.000 0.069(8) . . H19 H Uiso 0.0556(16) 0.9974(15) 0.2493(6) 1.000 0.014(4) . . H21A H Uiso 0.357(2) 1.0292(15) 0.3685(6) 1.000 0.024(5) . . H21B H Uiso 0.4282(18) 1.0642(15) 0.3197(6) 1.000 0.018(4) . . H23A H Uiso 0.70850 0.77620 0.38810 1.000 0.017(4) calc R H23B H Uiso 0.75760 0.80290 0.33500 1.000 0.024(5) calc R H27 H Uiso 0.81420 0.27690 0.32660 1.000 0.024(5) calc R H28 H Uiso 0.93070 0.42900 0.36340 1.000 0.031(5) calc R H29 H Uiso 0.83730 0.62380 0.37000 1.000 0.024(5) calc R H30 H Uiso 0.60860 0.20590 0.28450 1.000 0.027(5) calc R H31 H Uiso 0.39260 0.24100 0.25730 1.000 0.030(5) calc R H32 H Uiso 0.29640 0.43390 0.26350 1.000 0.019(4) calc R H33 H Uiso 0.41740 0.59030 0.29670 1.000 0.018(4) calc R H34A H Uiso -0.03850 0.93170 0.32050 1.000 0.026(5) calc R H34B H Uiso -0.14740 1.00690 0.29090 1.000 0.026(5) calc R H34C H Uiso -0.06990 1.06850 0.33430 1.000 0.029(5) calc R loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O4 0.0155(6) 0.0178(6) 0.0260(6) -0.0045(4) 0.0004(5) -0.0018(5) O3 0.0184(6) 0.0183(6) 0.0298(6) -0.0075(5) -0.0030(5) 0.0002(5) O1 0.0180(6) 0.0277(6) 0.0247(6) -0.0094(5) 0.0037(5) -0.0058(5) O2 0.0279(7) 0.0219(6) 0.0285(6) -0.0069(5) -0.0015(5) -0.0076(5) O5 0.0146(6) 0.0143(5) 0.0285(6) -0.0031(4) -0.0020(5) 0.0017(4) N1 0.0158(7) 0.0163(7) 0.0201(6) -0.0049(5) -0.0023(5) 0.0008(6) N2 0.0157(7) 0.0133(7) 0.0226(7) -0.0022(5) -0.0024(6) -0.0006(5) C4 0.0170(8) 0.0150(7) 0.0206(8) -0.0003(6) -0.0013(6) 0.0010(6) C1 0.0154(8) 0.0138(7) 0.0212(8) 0.0006(6) -0.0054(6) 0.0036(6) C5 0.0157(8) 0.0199(8) 0.0147(7) -0.0009(6) 0.0016(6) -0.0005(6) C8 0.0202(8) 0.0147(8) 0.0168(7) 0.0028(6) 0.0012(6) 0.0003(7) C3 0.0154(8) 0.0181(8) 0.0175(7) -0.0014(6) 0.0024(6) -0.0004(6) C11 0.0192(8) 0.0255(9) 0.0304(9) 0.0056(7) 0.0014(7) 0.0082(7) C17 0.0185(9) 0.0211(8) 0.0250(8) 0.0016(7) -0.0028(7) 0.0006(7) C14 0.0329(10) 0.0212(8) 0.0271(9) -0.0033(7) 0.0016(8) -0.0085(8) C9 0.0243(9) 0.0156(8) 0.0208(8) 0.0020(6) 0.0071(7) 0.0006(7) C16 0.0225(8) 0.0162(8) 0.0206(8) 0.0017(6) 0.0018(7) 0.0005(7) C13 0.0311(10) 0.0166(8) 0.0301(9) -0.0037(7) 0.0064(8) 0.0008(7) C12 0.0224(9) 0.0199(8) 0.0234(8) 0.0010(7) -0.0037(7) 0.0009(7) C7 0.0186(8) 0.0159(7) 0.0173(7) 0.0024(6) 0.0028(6) 0.0017(6) C6 0.0182(8) 0.0176(8) 0.0207(8) -0.0017(6) -0.0012(7) 0.0004(6) C2 0.0162(8) 0.0200(8) 0.0177(7) -0.0042(6) -0.0026(6) 0.0014(7) C15 0.0217(9) 0.0227(8) 0.0260(8) 0.0008(7) -0.0020(7) -0.0031(7) C10 0.0267(10) 0.0159(8) 0.0313(9) 0.0039(7) 0.0083(8) 0.0059(7) O9 0.0204(6) 0.0177(6) 0.0309(6) -0.0078(5) -0.0041(5) -0.0014(5) O8 0.0199(6) 0.0148(5) 0.0263(6) -0.0033(5) -0.0042(5) -0.0004(5) O7 0.0264(7) 0.0207(6) 0.0526(8) 0.0104(6) -0.0118(6) -0.0050(5) O6 0.0269(7) 0.0210(6) 0.0345(7) 0.0033(5) -0.0119(6) 0.0057(5) O10 0.0166(6) 0.0128(5) 0.0309(6) -0.0010(5) -0.0064(5) 0.0005(4) N4 0.0164(7) 0.0131(6) 0.0223(7) -0.0018(5) -0.0023(6) -0.0004(5) C22 0.0166(8) 0.0187(8) 0.0145(7) -0.0014(6) 0.0001(6) -0.0005(6) N3 0.0169(7) 0.0137(7) 0.0259(7) -0.0010(6) -0.0045(6) -0.0009(6) C25 0.0191(8) 0.0189(8) 0.0170(7) 0.0039(6) 0.0024(6) -0.0023(7) C18 0.0183(8) 0.0225(8) 0.0224(8) 0.0017(7) -0.0011(7) 0.0015(7) C29 0.0195(9) 0.0177(8) 0.0330(9) -0.0006(7) -0.0037(7) -0.0017(7) C20 0.0177(8) 0.0167(8) 0.0153(7) -0.0004(6) 0.0018(6) -0.0012(6) C23 0.0175(8) 0.0155(8) 0.0237(8) -0.0016(6) -0.0016(7) -0.0021(6) C24 0.0175(8) 0.0169(8) 0.0231(8) 0.0018(6) 0.0017(7) 0.0009(7) C31 0.0348(10) 0.0216(9) 0.0192(8) -0.0012(7) 0.0015(7) -0.0084(8) C26 0.0236(9) 0.0195(8) 0.0199(8) 0.0020(6) 0.0057(7) 0.0004(7) C21 0.0169(8) 0.0129(7) 0.0221(8) 0.0000(6) -0.0019(7) 0.0005(6) C34 0.0183(8) 0.0205(8) 0.0236(8) 0.0005(6) -0.0033(7) -0.0023(7) C19 0.0175(8) 0.0163(8) 0.0221(8) -0.0028(6) -0.0046(7) 0.0017(6) C28 0.0172(9) 0.0230(9) 0.0416(10) 0.0049(8) -0.0019(8) 0.0052(7) C27 0.0237(9) 0.0159(8) 0.0330(9) 0.0022(7) 0.0060(7) 0.0058(7) C33 0.0234(9) 0.0176(8) 0.0178(8) 0.0035(6) -0.0010(7) 0.0005(7) C32 0.0252(9) 0.0271(9) 0.0188(8) 0.0037(7) -0.0037(7) -0.0024(7) C30 0.0328(10) 0.0171(8) 0.0224(8) -0.0007(6) 0.0064(7) 0.0000(7) _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.3291(18) . . yes O2 C1 1.2012(19) . . yes O3 C3 1.2264(19) . . yes O4 C5 1.2424(19) . . yes O5 C6 1.4219(19) . . yes O5 C7 1.3747(19) . . yes O1 H1 0.89(3) . . no O6 C18 1.328(2) . . yes O7 C18 1.200(2) . . yes O8 C20 1.2317(18) . . yes O9 C22 1.2270(19) . . yes O10 C24 1.3741(19) . . yes O10 C23 1.4190(18) . . yes O6 H6 0.94(2) . . no N1 C3 1.337(2) . . yes N1 C2 1.448(2) . . yes N2 C5 1.319(2) . . yes N2 C4 1.445(2) . . yes N1 H1N 0.866(18) . . no N2 H2N 0.848(19) . . no N3 C19 1.448(2) . . yes N3 C20 1.331(2) . . yes N4 C22 1.332(2) . . yes N4 C21 1.440(2) . . yes N3 H3N 0.868(19) . . no N4 H4N 0.872(19) . . no C1 C2 1.525(2) . . no C2 C17 1.529(2) . . no C3 C4 1.517(2) . . no C5 C6 1.505(2) . . no C7 C8 1.426(2) . . no C7 C12 1.367(2) . . no C8 C9 1.421(2) . . no C8 C16 1.418(2) . . no C9 C10 1.415(2) . . no C9 C13 1.419(2) . . no C10 C11 1.360(2) . . no C11 C12 1.412(2) . . no C13 C14 1.361(3) . . no C14 C15 1.411(2) . . no C15 C16 1.370(2) . . no C2 H2 1.0000 . . no C4 H4A 0.9900 . . no C4 H4B 0.9900 . . no C6 H6B 0.9900 . . no C6 H6A 0.9900 . . no C10 H10 0.9500 . . no C11 H11 0.9500 . . no C12 H12 0.9500 . . no C13 H13 0.9500 . . no C14 H14 0.9500 . . no C15 H15 0.9500 . . no C16 H16 0.9500 . . no C17 H17C 0.9800 . . no C17 H17B 0.9800 . . no C17 H17A 0.9800 . . no C18 C19 1.519(2) . . no C19 C34 1.525(2) . . no C20 C21 1.511(2) . . no C22 C23 1.508(2) . . no C24 C25 1.423(2) . . no C24 C29 1.365(2) . . no C25 C26 1.420(2) . . no C25 C33 1.416(2) . . no C26 C27 1.417(2) . . no C26 C30 1.411(2) . . no C27 C28 1.357(2) . . no C28 C29 1.416(2) . . no C30 C31 1.368(3) . . no C31 C32 1.407(2) . . no C32 C33 1.368(2) . . no C19 H19 0.946(17) . . no C21 H21A 0.993(17) . . no C21 H21B 0.955(17) . . no C23 H23A 0.9900 . . no C23 H23B 0.9900 . . no C27 H27 0.9500 . . no C28 H28 0.9500 . . no C29 H29 0.9500 . . no C30 H30 0.9500 . . no C31 H31 0.9500 . . no C32 H32 0.9500 . . no C33 H33 0.9500 . . no C34 H34A 0.9800 . . no C34 H34B 0.9800 . . no C34 H34C 0.9800 . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 O5 C7 117.25(12) . . . yes C1 O1 H1 110.3(13) . . . no C23 O10 C24 117.03(12) . . . yes C18 O6 H6 110.0(17) . . . no C2 N1 C3 122.45(13) . . . yes C4 N2 C5 123.08(13) . . . yes C3 N1 H1N 119.1(13) . . . no C2 N1 H1N 118.0(13) . . . no C5 N2 H2N 119.0(13) . . . no C4 N2 H2N 117.9(13) . . . no C19 N3 C20 123.25(13) . . . yes C21 N4 C22 121.35(13) . . . yes C19 N3 H3N 118.7(12) . . . no C20 N3 H3N 117.7(12) . . . no C22 N4 H4N 121.1(13) . . . no C21 N4 H4N 117.5(13) . . . no O2 C1 C2 123.76(13) . . . yes O1 C1 C2 112.36(13) . . . yes O1 C1 O2 123.84(14) . . . yes N1 C2 C1 113.32(12) . . . yes C1 C2 C17 109.74(13) . . . no N1 C2 C17 108.74(13) . . . yes O3 C3 C4 122.25(14) . . . yes O3 C3 N1 124.61(14) . . . yes N1 C3 C4 113.10(13) . . . yes N2 C4 C3 109.24(12) . . . yes N2 C5 C6 117.13(14) . . . yes O4 C5 N2 123.25(14) . . . yes O4 C5 C6 119.60(14) . . . yes O5 C6 C5 109.21(13) . . . yes O5 C7 C12 123.77(14) . . . yes C8 C7 C12 121.52(15) . . . no O5 C7 C8 114.71(13) . . . yes C9 C8 C16 119.20(14) . . . no C7 C8 C16 122.85(14) . . . no C7 C8 C9 117.95(15) . . . no C8 C9 C10 119.49(15) . . . no C8 C9 C13 118.59(15) . . . no C10 C9 C13 121.92(15) . . . no C9 C10 C11 120.49(16) . . . no C10 C11 C12 121.16(16) . . . no C7 C12 C11 119.36(15) . . . no C9 C13 C14 120.96(15) . . . no C13 C14 C15 120.47(16) . . . no C14 C15 C16 120.31(16) . . . no C8 C16 C15 120.46(14) . . . no C1 C2 H2 108.00 . . . no C17 C2 H2 108.00 . . . no N1 C2 H2 108.00 . . . no H4A C4 H4B 108.00 . . . no C3 C4 H4B 110.00 . . . no N2 C4 H4A 110.00 . . . no N2 C4 H4B 110.00 . . . no C3 C4 H4A 110.00 . . . no C5 C6 H6A 110.00 . . . no O5 C6 H6A 110.00 . . . no C5 C6 H6B 110.00 . . . no O5 C6 H6B 110.00 . . . no H6A C6 H6B 108.00 . . . no C9 C10 H10 120.00 . . . no C11 C10 H10 120.00 . . . no C12 C11 H11 119.00 . . . no C10 C11 H11 119.00 . . . no C7 C12 H12 120.00 . . . no C11 C12 H12 120.00 . . . no C14 C13 H13 120.00 . . . no C9 C13 H13 119.00 . . . no C13 C14 H14 120.00 . . . no C15 C14 H14 120.00 . . . no C16 C15 H15 120.00 . . . no C14 C15 H15 120.00 . . . no C8 C16 H16 120.00 . . . no C15 C16 H16 120.00 . . . no C2 C17 H17B 109.00 . . . no C2 C17 H17C 109.00 . . . no C2 C17 H17A 109.00 . . . no H17A C17 H17C 109.00 . . . no H17B C17 H17C 109.00 . . . no H17A C17 H17B 110.00 . . . no O7 C18 C19 124.21(15) . . . yes O6 C18 O7 124.57(16) . . . yes O6 C18 C19 111.21(14) . . . yes C18 C19 C34 110.62(13) . . . no N3 C19 C18 108.05(13) . . . yes N3 C19 C34 111.99(14) . . . yes O8 C20 C21 120.93(14) . . . yes O8 C20 N3 124.33(15) . . . yes N3 C20 C21 114.74(13) . . . yes N4 C21 C20 110.04(13) . . . yes O9 C22 N4 123.78(15) . . . yes N4 C22 C23 117.28(14) . . . yes O9 C22 C23 118.94(14) . . . yes O10 C23 C22 110.43(13) . . . yes O10 C24 C25 114.43(14) . . . yes O10 C24 C29 123.96(14) . . . yes C25 C24 C29 121.60(15) . . . no C24 C25 C26 118.02(15) . . . no C26 C25 C33 119.07(14) . . . no C24 C25 C33 122.89(14) . . . no C25 C26 C30 118.75(16) . . . no C27 C26 C30 121.78(15) . . . no C25 C26 C27 119.46(15) . . . no C26 C27 C28 120.44(15) . . . no C27 C28 C29 121.13(16) . . . no C24 C29 C28 119.36(15) . . . no C26 C30 C31 120.93(16) . . . no C30 C31 C32 120.33(16) . . . no C31 C32 C33 120.29(16) . . . no C25 C33 C32 120.61(15) . . . no N3 C19 H19 109.9(10) . . . no C18 C19 H19 108.0(10) . . . no C34 C19 H19 108.2(10) . . . no N4 C21 H21A 109.2(10) . . . no N4 C21 H21B 109.7(10) . . . no C20 C21 H21A 109.3(11) . . . no C20 C21 H21B 108.5(11) . . . no H21A C21 H21B 110.1(14) . . . no O10 C23 H23A 110.00 . . . no O10 C23 H23B 110.00 . . . no C22 C23 H23A 110.00 . . . no C22 C23 H23B 110.00 . . . no H23A C23 H23B 108.00 . . . no C26 C27 H27 120.00 . . . no C28 C27 H27 120.00 . . . no C27 C28 H28 119.00 . . . no C29 C28 H28 119.00 . . . no C24 C29 H29 120.00 . . . no C28 C29 H29 120.00 . . . no C26 C30 H30 119.00 . . . no C31 C30 H30 120.00 . . . no C30 C31 H31 120.00 . . . no C32 C31 H31 120.00 . . . no C31 C32 H32 120.00 . . . no C33 C32 H32 120.00 . . . no C25 C33 H33 120.00 . . . no C32 C33 H33 120.00 . . . no C19 C34 H34A 110.00 . . . no C19 C34 H34B 109.00 . . . no C19 C34 H34C 110.00 . . . no H34A C34 H34B 109.00 . . . no H34A C34 H34C 109.00 . . . no H34B C34 H34C 109.00 . . . no 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 C7 O5 C6 C5 -169.50(12) . . . . no C6 O5 C7 C8 166.48(13) . . . . no C6 O5 C7 C12 -13.1(2) . . . . no C23 O10 C24 C29 9.6(2) . . . . no C24 O10 C23 C22 178.37(12) . . . . no C23 O10 C24 C25 -171.51(13) . . . . no C3 N1 C2 C17 148.25(14) . . . . no C3 N1 C2 C1 -89.44(17) . . . . no C2 N1 C3 O3 10.9(2) . . . . no C2 N1 C3 C4 -166.73(13) . . . . no C5 N2 C4 C3 -169.41(14) . . . . no C4 N2 C5 C6 176.26(14) . . . . no C4 N2 C5 O4 -2.0(2) . . . . no C20 N3 C19 C34 76.64(19) . . . . no C19 N3 C20 O8 3.9(2) . . . . no C20 N3 C19 C18 -161.29(14) . . . . no C19 N3 C20 C21 -176.44(14) . . . . no C21 N4 C22 O9 1.8(2) . . . . no C22 N4 C21 C20 168.15(14) . . . . no C21 N4 C22 C23 -177.50(14) . . . . no O1 C1 C2 N1 -54.28(17) . . . . no O1 C1 C2 C17 67.47(16) . . . . no O2 C1 C2 C17 -110.54(17) . . . . no O2 C1 C2 N1 127.70(16) . . . . no O3 C3 C4 N2 11.7(2) . . . . no N1 C3 C4 N2 -170.67(13) . . . . no O4 C5 C6 O5 179.04(13) . . . . no N2 C5 C6 O5 0.71(19) . . . . no C12 C7 C8 C9 0.8(2) . . . . no O5 C7 C8 C16 0.8(2) . . . . no C8 C7 C12 C11 0.3(2) . . . . no C12 C7 C8 C16 -179.68(15) . . . . no O5 C7 C12 C11 179.77(14) . . . . no O5 C7 C8 C9 -178.77(13) . . . . no C16 C8 C9 C10 178.89(15) . . . . no C16 C8 C9 C13 -1.2(2) . . . . no C7 C8 C16 C15 -179.45(15) . . . . no C9 C8 C16 C15 0.1(2) . . . . no C7 C8 C9 C10 -1.6(2) . . . . no C7 C8 C9 C13 178.31(14) . . . . no C8 C9 C10 C11 1.3(2) . . . . no C10 C9 C13 C14 -178.49(16) . . . . no C13 C9 C10 C11 -178.55(16) . . . . no C8 C9 C13 C14 1.6(2) . . . . no C9 C10 C11 C12 -0.3(3) . . . . no C10 C11 C12 C7 -0.5(3) . . . . no C9 C13 C14 C15 -0.9(3) . . . . no C13 C14 C15 C16 -0.4(3) . . . . no C14 C15 C16 C8 0.7(2) . . . . no O6 C18 C19 N3 175.49(13) . . . . no O6 C18 C19 C34 -61.60(18) . . . . no O7 C18 C19 N3 -6.2(2) . . . . no O7 C18 C19 C34 116.76(19) . . . . no O8 C20 C21 N4 8.6(2) . . . . no N3 C20 C21 N4 -171.11(13) . . . . no O9 C22 C23 O10 -179.11(13) . . . . no N4 C22 C23 O10 0.22(19) . . . . no O10 C24 C25 C26 -179.16(13) . . . . no O10 C24 C25 C33 -0.6(2) . . . . no C29 C24 C25 C26 -0.3(2) . . . . no C29 C24 C25 C33 178.28(15) . . . . no O10 C24 C29 C28 178.99(14) . . . . no C25 C24 C29 C28 0.2(2) . . . . no C24 C25 C26 C27 0.2(2) . . . . no C24 C25 C26 C30 178.85(14) . . . . no C33 C25 C26 C27 -178.45(14) . . . . no C33 C25 C26 C30 0.2(2) . . . . no C24 C25 C33 C32 -177.30(15) . . . . no C26 C25 C33 C32 1.2(2) . . . . no C25 C26 C27 C28 0.0(2) . . . . no C30 C26 C27 C28 -178.65(16) . . . . no C25 C26 C30 C31 -1.6(2) . . . . no C27 C26 C30 C31 177.10(16) . . . . no C26 C27 C28 C29 -0.1(3) . . . . no C27 C28 C29 C24 -0.1(3) . . . . no C26 C30 C31 C32 1.4(3) . . . . no C30 C31 C32 C33 0.1(3) . . . . no C31 C32 C33 C25 -1.4(2) . . . . no 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 _geom_hbond_publ_flag O1 H1 O4 0.89(3) 1.78(3) 2.6581(16) 169(2) 1_655 yes N1 H1N O9 0.866(18) 2.076(18) 2.9120(18) 162.0(17) 1_545 yes N2 H2N O3 0.848(19) 2.319(18) 2.6784(18) 105.9(14) . yes N2 H2N O5 0.848(19) 2.169(19) 2.5800(17) 109.5(15) . yes N3 H3N O4 0.868(19) 2.365(18) 3.1193(18) 145.6(15) 1_565 yes N3 H3N O7 0.868(19) 2.355(18) 2.6732(18) 102.0(13) . yes N4 H4N O8 0.872(19) 2.267(19) 2.6605(18) 107.4(15) . yes N4 H4N O10 0.872(19) 2.237(19) 2.6178(17) 106.2(15) . yes O6 H6 O8 0.94(2) 1.74(3) 2.6428(16) 160(3) 4_555 yes C4 H4A O9 0.9900 2.5600 3.2083(19) 123.00 1_545 yes C6 H6B O2 0.9900 2.6000 3.418(2) 140.00 1_455 yes C14 H14 O2 0.9500 2.5300 3.276(2) 136.00 3_466 yes C17 H17B O3 0.9800 2.4900 3.411(2) 156.00 3_556 yes C34 H34C O1 0.9800 2.5100 3.444(2) 158.00 1_465 yes _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.10 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.230 _refine_diff_density_min -0.160 _refine_diff_density_rms 0.039