# Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 186/1799 data_global _audit_creation_method 'SHELXL and manual editing' #======================================================================= _publ_section_title ; A new bus-(\m-alkoxo) diiron(III) complex and its implication on the number of Fe(III)-phenolate bonds and the redox potential in uteroferrin ; _publ_contact_author_name 'Dr Ivo Vencato' _publ_contact_author_address ; Depto. Qu\'imica - UFSC 88040 - 900 Florian\'opolis, SC Brazil ; _publ_contact_author_email vencato@qmc.ufsc.br _publ_contact_author_fax '55(48)3316888' _publ_contact_author_phone '55(48)3316826' _publ_contact_letter ; Please consider this CIF as supplementary material for publication in Dalton Transactions as a full paper. ; _publ_requested_journal ; Journal of the Chemical Society, Dalton Transactions ; loop_ _publ_author_name _publ_author_address 'Neves, Ademir' ; Depto. Qu\'imica - UFSC 88040-900 - Florian\'opolis, SC Brazil ; 'Rossi, Liane M.' ; Depto. Qu\'imica - UFSC 88040-900 - Florian\'opolis, SC Brazil ; 'Vencato, Ivo' ; Depto. Qu\'imica - UFSC 88040-900 - Florian\'opolis, SC Brazil ; 'Haase, Wolfgang' ; Institut f\"ur Physikalische Chemie - TUD D-64287 - Darmstadt Germany ; 'Werner, R\"udiger' ; Institut f\"ur Physikalische Chemie - TUD D-64287 - Darmstadt Germany ; _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H21 Fe N2 O4' _chemical_formula_weight 373.21 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' 'Fe' 'Fe' 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.653(2) _cell_length_b 9.754(2) _cell_length_c 9.848(2) _cell_angle_alpha 89.02(3) _cell_angle_beta 80.92(3) _cell_angle_gamma 66.11(3) _cell_volume 836.1(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 8.32 _cell_measurement_theta_max 14.39 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.483 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 390 _exptl_absorpt_coefficient_mu 0.925 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details 'PLATON (Spek, 1990)' _exptl_absorpt_correction_T_min 0.85689 _exptl_absorpt_correction_T_max 0.96514 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius CAD-4 diffractometer' _diffrn_measurement_method \w--2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 3600 _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 3131 _diffrn_reflns_av_R_equivalents 0.0425 _diffrn_reflns_av_sigmaI/netI 0.0800 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.87 _diffrn_reflns_theta_max 24.97 _reflns_number_total 2939 _reflns_number_gt 2016 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD-4 EXPRESS (Enraf-Nonius, 1994)' _computing_cell_refinement ; SET4 in CAD-4 EXPRESS (Enraf-Nonius, 1994) ; _computing_data_reduction 'HELENA (Spek, 1996)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ZORTEP (Zsolnai, 1996)' _computing_publication_material ; SHELXL-97. All calculations were performed on a DEC 3000 AXP and PC/486 computer ; _publ_section_references ; Enraf-Nonius (1994). CAD-4 EXPRESS. Version 5.1/1.2. Enraf-Nonius, Delft, The Netherlands. Fair, C. K. (1990). MolEN. An Interactive Intelligent System for Crystal Structure Analysis. Enraf-Nonius, Delft, The Netherlands. Sheldrick, G. M. (1990). SHELXS97. Program for the Solution of Crystal Structures. Univ. of G\"ottingen, Germany. Sheldrick, G. M. (1997). SHELXL97. Program for the Refinement of Crystal Structures. Univ. of G\"ottingen, Germany. Spek, A. L. (1990). Acta Cryst. A36, C--34. Spek, A. L. (1996). Program for Reduction of CAD-4 Data. University of Utrecht. The Netherlands. Zsolnai, L. (1966). ZORTEP. An Interactive ORTEP Program. University of Heidelberg, Heidelberg, Germany. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0061P)^2^+1.6946P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0013(9) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2939 _refine_ls_number_parameters 224 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1065 _refine_ls_R_factor_gt 0.0487 _refine_ls_wR_factor_ref 0.1128 _refine_ls_wR_factor_gt 0.0843 _refine_ls_goodness_of_fit_ref 1.154 _refine_ls_restrained_S_all 1.154 _refine_ls_shift/su_max 0.044 _refine_ls_shift/su_mean 0.002 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Fe Fe 0.67623(8) 0.42825(8) 0.94387(7) 0.0278(2) Uani 1 d . . . O1 O 0.7138(4) 0.5984(3) 0.8792(3) 0.0337(8) Uani 1 d . . . O2 O 0.8647(3) 0.3199(4) 1.0091(3) 0.0362(8) Uani 1 d . . . O3 O 0.4669(3) 0.4789(3) 0.8827(3) 0.0269(7) Uani 1 d . . . N1 N 0.7521(5) 0.3299(4) 0.7335(4) 0.0370(10) Uani 1 d . . . H1 H 0.8071 0.2295 0.7388 0.055 Uiso 1 calc R . . N2 N 0.6291(5) 0.2253(4) 0.9775(5) 0.0406(11) Uani 1 d . . . H2 H 0.5606 0.2491 1.0574 0.061 Uiso 1 calc R . . C1 C 0.8550(6) 0.3897(6) 0.6480(5) 0.0433(14) Uani 1 d . . . H1A H 0.8883 0.3392 0.5573 0.065 Uiso 1 calc R . . H1B H 0.9456 0.3683 0.6899 0.065 Uiso 1 calc R . . C2 C 0.7534(6) 0.0885(5) 1.0059(5) 0.0401(13) Uani 1 d . . . H2A H 0.8287 0.0502 0.9228 0.060 Uiso 1 calc R . . H2B H 0.7133 0.0136 1.0323 0.060 Uiso 1 calc R . . C3 C 0.6126(6) 0.3490(6) 0.6752(5) 0.0425(13) Uani 1 d . . . H3A H 0.6353 0.2653 0.6111 0.064 Uiso 1 calc R . . H3B H 0.5783 0.4409 0.6263 0.064 Uiso 1 calc R . . C4 C 0.5398(6) 0.2113(5) 0.8739(5) 0.0365(12) Uani 1 d . . . H4A H 0.4504 0.1965 0.9191 0.055 Uiso 1 calc R . . H4B H 0.6024 0.1253 0.8111 0.055 Uiso 1 calc R . . C5 C 0.4888(6) 0.3554(5) 0.7936(5) 0.0330(12) Uani 1 d . . . H5 H 0.3934 0.3722 0.7596 0.050 Uiso 1 calc R . . C11 C 0.7102(5) 0.6515(5) 0.7521(5) 0.0334(12) Uani 1 d . . . C12 C 0.7767(6) 0.5555(6) 0.6338(5) 0.0381(12) Uani 1 d . . . C13 C 0.7704(7) 0.6154(7) 0.5050(6) 0.0514(15) Uani 1 d . . . H13 H 0.8136 0.5514 0.4265 0.062 Uiso 1 calc R . . C14 C 0.7015(7) 0.7678(7) 0.4913(6) 0.0569(16) Uani 1 d . . . H14 H 0.6984 0.8065 0.4043 0.068 Uiso 1 calc R . . C15 C 0.6373(7) 0.8623(7) 0.6071(6) 0.0563(17) Uani 1 d . . . H15 H 0.5911 0.9654 0.5983 0.068 Uiso 1 calc R . . C16 C 0.6408(6) 0.8056(6) 0.7364(6) 0.0466(14) Uani 1 d . . . H16 H 0.5963 0.8710 0.8139 0.056 Uiso 1 calc R . . C21 C 0.8849(5) 0.2265(5) 1.1122(5) 0.0351(12) Uani 1 d . . . C22 C 0.8299(6) 0.1125(5) 1.1179(5) 0.0365(12) Uani 1 d . . . C23 C 0.8533(7) 0.0188(6) 1.2281(6) 0.0509(15) Uani 1 d . . . H23 H 0.8139 -0.0542 1.2350 0.061 Uiso 1 calc R . . C24 C 0.9336(7) 0.0324(7) 1.3269(6) 0.0605(17) Uani 1 d . . . H24 H 0.9497 -0.0319 1.3993 0.073 Uiso 1 calc R . . C25 C 0.9899(7) 0.1414(7) 1.3180(6) 0.0572(16) Uani 1 d . . . H25 H 1.0457 0.1497 1.3839 0.069 Uiso 1 calc R . . C26 C 0.9646(6) 0.2386(6) 1.2127(5) 0.0465(14) Uani 1 d . . . H26 H 1.0015 0.3132 1.2092 0.056 Uiso 1 calc R . . OW O 0.1490(6) 0.3270(7) 0.8899(5) 0.093(2) Uani 1 d . . . H1W H 0.161(9) 0.360(9) 0.959(8) 0.112 Uiso 1 d . . . H2W H 0.054(9) 0.335(8) 0.922(8) 0.112 Uiso 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 Fe 0.0266(4) 0.0255(4) 0.0336(4) 0.0036(3) -0.0081(3) -0.0119(3) O1 0.044(2) 0.0322(19) 0.0319(19) 0.0046(15) -0.0057(16) -0.0225(16) O2 0.0267(18) 0.0365(19) 0.049(2) 0.0153(17) -0.0140(16) -0.0144(16) O3 0.0267(18) 0.0261(17) 0.0305(18) 0.0006(14) -0.0080(14) -0.0123(14) N1 0.035(2) 0.032(2) 0.040(3) 0.0004(19) -0.003(2) -0.011(2) N2 0.038(3) 0.028(2) 0.058(3) 0.007(2) -0.020(2) -0.011(2) C1 0.033(3) 0.044(3) 0.042(3) -0.001(3) 0.012(2) -0.012(3) C2 0.040(3) 0.029(3) 0.051(3) 0.013(2) -0.013(3) -0.013(2) C3 0.053(4) 0.041(3) 0.035(3) -0.004(2) -0.006(3) -0.021(3) C4 0.043(3) 0.027(3) 0.045(3) -0.003(2) -0.013(3) -0.016(2) C5 0.036(3) 0.035(3) 0.035(3) -0.004(2) -0.009(2) -0.020(2) C11 0.033(3) 0.034(3) 0.042(3) 0.007(2) -0.007(2) -0.023(2) C12 0.031(3) 0.040(3) 0.041(3) 0.009(3) -0.003(2) -0.013(2) C13 0.055(4) 0.067(4) 0.041(3) 0.003(3) -0.005(3) -0.035(3) C14 0.072(4) 0.066(4) 0.050(4) 0.022(3) -0.019(3) -0.042(4) C15 0.074(4) 0.042(3) 0.069(4) 0.027(3) -0.032(4) -0.033(3) C16 0.059(4) 0.039(3) 0.051(4) 0.005(3) -0.011(3) -0.028(3) C21 0.025(3) 0.030(3) 0.040(3) 0.001(2) -0.006(2) -0.001(2) C22 0.036(3) 0.025(3) 0.040(3) 0.006(2) -0.004(2) -0.005(2) C23 0.058(4) 0.042(3) 0.051(4) 0.013(3) -0.005(3) -0.020(3) C24 0.081(5) 0.061(4) 0.037(3) 0.020(3) -0.020(3) -0.024(4) C25 0.068(4) 0.052(4) 0.042(4) -0.004(3) -0.019(3) -0.011(3) C26 0.049(4) 0.043(3) 0.044(3) 0.002(3) -0.015(3) -0.013(3) OW 0.067(3) 0.142(5) 0.090(4) -0.043(4) 0.018(3) -0.071(4) _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 Fe O2 1.905(3) . ? Fe O1 1.916(3) . ? Fe O3 1.985(3) 2_667 ? Fe O3 2.063(3) . ? Fe N1 2.184(4) . ? Fe N2 2.212(4) . ? O1 C11 1.346(5) . ? O2 C21 1.336(5) . ? O3 C5 1.428(5) . ? O3 Fe 1.985(3) 2_667 ? N1 C3 1.489(6) . ? N1 C1 1.492(6) . ? N2 C2 1.448(6) . ? N2 C4 1.476(6) . ? C1 C12 1.497(7) . ? C2 C22 1.491(7) . ? C3 C5 1.514(6) . ? C4 C5 1.538(6) . ? C11 C16 1.394(7) . ? C11 C12 1.400(7) . ? C12 C13 1.387(7) . ? C13 C14 1.375(8) . ? C14 C15 1.373(8) . ? C15 C16 1.380(7) . ? C21 C26 1.379(7) . ? C21 C22 1.411(7) . ? C22 C23 1.393(7) . ? C23 C24 1.376(8) . ? C24 C25 1.372(8) . ? C25 C26 1.376(7) . ? 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 O2 Fe O1 98.69(14) . . ? O2 Fe O3 101.99(14) . 2_667 ? O1 Fe O3 99.17(13) . 2_667 ? O2 Fe O3 161.13(12) . . ? O1 Fe O3 99.75(13) . . ? O3 Fe O3 78.94(13) 2_667 . ? O2 Fe N1 96.88(15) . . ? O1 Fe N1 88.57(14) . . ? O3 Fe N1 158.20(14) 2_667 . ? O3 Fe N1 79.67(14) . . ? O2 Fe N2 86.82(14) . . ? O1 Fe N2 169.10(15) . . ? O3 Fe N2 88.78(14) 2_667 . ? O3 Fe N2 74.33(13) . . ? N1 Fe N2 81.40(16) . . ? C11 O1 Fe 128.0(3) . . ? C21 O2 Fe 126.0(3) . . ? C5 O3 Fe 133.0(3) . 2_667 ? C5 O3 Fe 105.7(3) . . ? Fe O3 Fe 101.06(13) 2_667 . ? C3 N1 C1 114.2(4) . . ? C3 N1 Fe 107.5(3) . . ? C1 N1 Fe 112.9(3) . . ? C2 N2 C4 116.3(4) . . ? C2 N2 Fe 117.9(3) . . ? C4 N2 Fe 109.8(3) . . ? N1 C1 C12 112.0(4) . . ? N2 C2 C22 112.2(4) . . ? N1 C3 C5 107.8(4) . . ? N2 C4 C5 109.0(4) . . ? O3 C5 C3 105.7(4) . . ? O3 C5 C4 108.7(4) . . ? C3 C5 C4 111.5(4) . . ? O1 C11 C16 119.8(5) . . ? O1 C11 C12 121.6(4) . . ? C16 C11 C12 118.6(5) . . ? C13 C12 C11 119.5(5) . . ? C13 C12 C1 120.9(5) . . ? C11 C12 C1 119.6(4) . . ? C14 C13 C12 121.2(6) . . ? C15 C14 C13 119.4(5) . . ? C14 C15 C16 120.6(5) . . ? C15 C16 C11 120.7(5) . . ? O2 C21 C26 119.7(5) . . ? O2 C21 C22 121.1(4) . . ? C26 C21 C22 119.2(5) . . ? C23 C22 C21 118.7(5) . . ? C23 C22 C2 120.4(5) . . ? C21 C22 C2 120.9(4) . . ? C24 C23 C22 121.1(5) . . ? C25 C24 C23 119.5(5) . . ? C24 C25 C26 120.7(6) . . ? C25 C26 C21 120.8(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 O2 Fe O1 C11 123.9(4) . . . . ? O3 Fe O1 C11 -132.3(4) 2_667 . . . ? O3 Fe O1 C11 -52.1(4) . . . . ? N1 Fe O1 C11 27.2(4) . . . . ? N2 Fe O1 C11 4.1(10) . . . . ? O1 Fe O2 C21 150.8(4) . . . . ? O3 Fe O2 C21 49.4(4) 2_667 . . . ? O3 Fe O2 C21 -41.4(7) . . . . ? N1 Fe O2 C21 -119.6(4) . . . . ? N2 Fe O2 C21 -38.7(4) . . . . ? O2 Fe O3 C5 -46.2(5) . . . . ? O1 Fe O3 C5 121.5(3) . . . . ? O3 Fe O3 C5 -141.0(3) 2_667 . . . ? N1 Fe O3 C5 34.8(3) . . . . ? N2 Fe O3 C5 -49.1(3) . . . . ? O2 Fe O3 Fe 94.7(4) . . . 2_667 ? O1 Fe O3 Fe -97.54(14) . . . 2_667 ? O3 Fe O3 Fe 0.0 2_667 . . 2_667 ? N1 Fe O3 Fe 175.73(15) . . . 2_667 ? N2 Fe O3 Fe 91.85(16) . . . 2_667 ? O2 Fe N1 C3 158.0(3) . . . . ? O1 Fe N1 C3 -103.4(3) . . . . ? O3 Fe N1 C3 8.2(5) 2_667 . . . ? O3 Fe N1 C3 -3.2(3) . . . . ? N2 Fe N1 C3 72.3(3) . . . . ? O2 Fe N1 C1 -75.1(3) . . . . ? O1 Fe N1 C1 23.5(3) . . . . ? O3 Fe N1 C1 135.0(4) 2_667 . . . ? O3 Fe N1 C1 123.7(3) . . . . ? N2 Fe N1 C1 -160.8(3) . . . . ? O2 Fe N2 C2 -11.2(4) . . . . ? O1 Fe N2 C2 109.6(8) . . . . ? O3 Fe N2 C2 -113.2(4) 2_667 . . . ? O3 Fe N2 C2 167.9(4) . . . . ? N1 Fe N2 C2 86.3(4) . . . . ? O2 Fe N2 C4 -147.4(3) . . . . ? O1 Fe N2 C4 -26.6(10) . . . . ? O3 Fe N2 C4 110.5(3) 2_667 . . . ? O3 Fe N2 C4 31.6(3) . . . . ? N1 Fe N2 C4 -50.0(3) . . . . ? C3 N1 C1 C12 62.0(6) . . . . ? Fe N1 C1 C12 -61.2(5) . . . . ? C4 N2 C2 C22 -176.3(4) . . . . ? Fe N2 C2 C22 50.2(5) . . . . ? C1 N1 C3 C5 -153.4(4) . . . . ? Fe N1 C3 C5 -27.2(4) . . . . ? C2 N2 C4 C5 -146.0(4) . . . . ? Fe N2 C4 C5 -8.9(5) . . . . ? Fe O3 C5 C3 177.3(3) 2_667 . . . ? Fe O3 C5 C3 -60.3(4) . . . . ? Fe O3 C5 C4 -62.9(5) 2_667 . . . ? Fe O3 C5 C4 59.5(4) . . . . ? N1 C3 C5 O3 58.4(5) . . . . ? N1 C3 C5 C4 -59.5(5) . . . . ? N2 C4 C5 O3 -31.2(5) . . . . ? N2 C4 C5 C3 84.9(5) . . . . ? Fe O1 C11 C16 137.3(4) . . . . ? Fe O1 C11 C12 -43.6(6) . . . . ? O1 C11 C12 C13 -179.8(5) . . . . ? C16 C11 C12 C13 -0.7(7) . . . . ? O1 C11 C12 C1 -0.5(7) . . . . ? C16 C11 C12 C1 178.6(5) . . . . ? N1 C1 C12 C13 -125.7(5) . . . . ? N1 C1 C12 C11 55.0(6) . . . . ? C11 C12 C13 C14 0.7(8) . . . . ? C1 C12 C13 C14 -178.6(5) . . . . ? C12 C13 C14 C15 -0.2(9) . . . . ? C13 C14 C15 C16 -0.3(9) . . . . ? C14 C15 C16 C11 0.3(9) . . . . ? O1 C11 C16 C15 179.3(5) . . . . ? C12 C11 C16 C15 0.2(8) . . . . ? Fe O2 C21 C26 -132.6(4) . . . . ? Fe O2 C21 C22 49.3(6) . . . . ? O2 C21 C22 C23 -179.6(4) . . . . ? C26 C21 C22 C23 2.2(7) . . . . ? O2 C21 C22 C2 2.6(7) . . . . ? C26 C21 C22 C2 -175.5(5) . . . . ? N2 C2 C22 C23 129.8(5) . . . . ? N2 C2 C22 C21 -52.5(6) . . . . ? C21 C22 C23 C24 -2.6(8) . . . . ? C2 C22 C23 C24 175.1(5) . . . . ? C22 C23 C24 C25 1.0(9) . . . . ? C23 C24 C25 C26 1.1(9) . . . . ? C24 C25 C26 C21 -1.4(9) . . . . ? O2 C21 C26 C25 -178.5(5) . . . . ? C22 C21 C26 C25 -0.3(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 N2 H2 O1 0.91 2.44 3.147(6) 135.1 2_667 OW H1W O1 0.81(7) 2.27(8) 3.040(6) 159(8) 2_667 OW H2W O2 0.89(7) 1.95(7) 2.837(6) 169(7) 1_455 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.641 _refine_diff_density_min -0.391 _refine_diff_density_rms 0.099