# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_address # Address of author for correspondence ; Crystal Structure Center, Chemical Physics, Zernike Institute for Advanced Materials, University of Groningen, Nijenborgh 4, NL-9747 AG Groningen, The Netherlands. ; _publ_contact_author_email A.Meetsma@rug.nl _publ_contact_author_fax '+31 50 3634441' _publ_contact_author_phone '+31 50 3634368' #=============================================================================== # 1. SUBMISSION DETAILS _publ_contact_author_name # Name of author for correspondence ; Drs. A. Meetsma ; _publ_contact_letter # Include date of submission ; Dat of submission : 2010-03-09 12:02:46 Consider this CIF submission for deposition of the X-ray structure of a manuscript to be submitted to : Dalton (Our Compound_Identification_Code : q1539) ; # Publication choise FI, CI or EI for Inorganic # FM, CM or EM for Metal-organic # FO, CO or EO for Organic _publ_requested_category ? _publ_requested_coeditor_name ? loop_ _publ_author_name 'Pijper, Dirk' 'Saisaha, Pattama' 'Alsters, Paul' 'Boer, Johannes' 'Hoen, Rob' 'Smit, Christian' 'Meetsma, Auke' 'Hage, Ronald' 'van Summeren, Ruben' 'Feringa, Ben' 'Browne, Wesley' data_q1539 _database_code_depnum_ccdc_archive 'CCDC 768839' #TrackingRef 'q1539.cif' #============================================================================== # 0. AUDIT DETAILS _audit_creation_date '2010-03-09 11:02:46' _audit_creation_method ; PLATON option (version :: 200110) SHELXL97-2 & Manual Editing ; _audit_update_record ; ? 2010-03-09 # Formatted by publCIF ; #=============================================================================== _publ_section_exptl_refinement ; Refinement was frustrated by a disorder problem: from the solution, it was clear that the positions of one of the perchlorate anions was highly disordered. The smeared electron density for O5 and O6 has been described by two site occupancy factors with separately refined displacement parameters. The s.o.f. of the major fraction of the component of the disorder model refined to a value of 0.593(6). The atoms of the disordered anion showed unrealistic displacement parameters when allowed to vary anisotropically, suggesting dynamic disorder (dynamic means that the smeared electron density is due to fluctuations of the atomic positions within each unit cell; the disorder is compensated by the large displacement parameters). The hydrogen atoms were generated by geometrical considerations, constrained to idealized geometries, and allowed to ride on the carrier atom with an isotropic displacement parameter related to the equivalent displacement parameter of their carrier atoms, with U~iso~(H) = 1.2U~eq~(C) or 1.5U~eq~(methyl C). The methyl-groups were refined as rigid groups, which were allowed to rotate freely. Assigned values of bond distances for secondary C---H~2~ = 0.99 \%A, methyl C---H~3~ = 0.98 \%A, aromatic C---H = 0.95 \%A and N---H = 0.93 ; _publ_section_related_literature ; ; # Insert blank lines between references _publ_section_references ; Beurskens, P. T., Beurskens, G., de Gelder, R., Smits, J. M. M., Garc\'ia-Granda, S. & Gould, R. O. (2008). The DIRDIF08 program system, Technical Report of the Crystallography Laboratory, University of Nijmegen, The Netherlands. Bruker, (2007). SMART (Version 5.632), SAINT-Plus (Version 7.46a) and SADABS (Version 2.10). Bruker AXS Inc., Madison, Wisconsin, USA. Meetsma, A. (2010). Extended version of the program PLUTO. University of Groningen, The Netherlands. (unpublished). Sheldrick, G. M. (2008). Acta Cryst. A64, 112--122. Spek, A. L. (2003). J. Appl. Cryst.36, 7--13. ; _publ_section_figure_captions ; Fig. 1. Perspective PLUTO drawings of the molecule illustrating the configuration and the adopted numbering scheme. Fig. 2. Molecular packing viewed down unit cell axes. Fig. 3. Perspective ORTEP drawing of the title compound. Displacement ellipsoids for non-H atoms are represented at the 50% probability level. The H-atoms have been omitted to improve clarity. ; _publ_section_acknowledgements ; ? ; #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H28 Fe N5 O2, 0.5(C2 H3 N), 2(Cl O4)' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C23 H29.5 Cl2 Fe N5.5 O10' _chemical_formula_iupac ? _chemical_formula_weight 669.77 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 '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' Fe Fe 0.3463 0.8444 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 2/c' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,y,1/2-z 3 -x,-y,-z 4 x,-y,1/2+z 5 1/2+x,1/2+y,z 6 1/2-x,1/2+y,1/2-z 7 1/2-x,1/2-y,-z 8 1/2+x,1/2-y,1/2+z _cell_length_a 37.597(4) _cell_length_b 9.1237(10) _cell_length_c 16.3513(18) _cell_angle_alpha 90 _cell_angle_beta 102.216(1) _cell_angle_gamma 90 _cell_volume 5481.9(10) _cell_formula_units_Z 8 _cell_measurement_temperature 100(1) _cell_measurement_reflns_used 7754 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 29.17 _cell_special_details ; The final unit cell was obtained from the xyz centroids of 7754 reflections after integration using the SAINTPLUS software package (Bruker, 2007). Reduced cell calculations did not indicate any higher metric lattice symmetry and examination of the final atomic coordinates of the structure did not yield extra symmetry elements (Spek, 1988; Le Page 1987, 1988) ; _exptl_crystal_description platelet _exptl_crystal_colour red _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.17 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.623 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2768 _exptl_absorpt_coefficient_mu 0.812 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS, (Bruker, 2007))' _exptl_absorpt_correction_T_min 0.6703 _exptl_absorpt_correction_T_max 0.8714 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 100(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine focus sealed Siemens Mo tube ' _diffrn_radiation_monochromator 'parallel mounted graphite' _diffrn_radiation_detector ; CCD area-detector ; _diffrn_measurement_device_type ; Bruker Smart Apex; CCD area detector ; _diffrn_measurement_method '\f and \w scans' _diffrn_special_details ; Crystal into the cold nitrogen stream of the low-temparature unit (KRYOFLEX, (Bruker, 2007)). ; _diffrn_detector_area_resol_mean 66.06 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% 0 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? # number of measured reflections (redundant set) _diffrn_reflns_number 21142 _diffrn_reflns_av_R_equivalents 0.0328 _diffrn_reflns_av_sigmaI/netI 0.0322 _diffrn_reflns_limit_h_min -45 _diffrn_reflns_limit_h_max 46 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.55 _diffrn_reflns_theta_max 26.37 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_reduction_process ; Intensity data were corrected for Lorentz and polarization effects, decay and absorption and reduced to F~o~^2^ using SAINT-Plus & SADABS (Bruker, 2007). ; # number of unique reflections _reflns_number_total 5616 _reflns_number_gt 4780 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2007)' _computing_cell_refinement 'SAINT-Plus (Bruker, 2007)' _computing_data_reduction 'SAINT-Plus (Bruker, 2007)' _computing_structure_solution ; DIRDIF-08 (Beurskens et al., 2008) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; PLATON (Spek, 2003) PLUTO (Meetsma, 2010) ; _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _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^)+(0.0557P)^2^+10.23P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary heavy _atom_sites_solution_secondary direct _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _chemical_absolute_configuration . _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 5616 _refine_ls_number_parameters 397 _refine_ls_number_restraints 0 _refine_ls_number_constraints ? _refine_ls_R_factor_all 0.0527 _refine_ls_R_factor_gt 0.0444 _refine_ls_wR_factor_ref 0.1118 _refine_ls_wR_factor_gt 0.1071 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.925 _refine_diff_density_min -0.489 _refine_diff_density_rms 0.083 _vrn_publ_code_number_frames 1800 _vrn_publ_code_frame_time_sec 10.0 _vrn_publ_code_meas_time_hour 7.8 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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 Fe1 Fe Uani 0.13041(1) 0.19943(4) 0.46519(2) 1.0 0.0192(1) . . O1 O Uani 0.10032(4) 0.11840(19) 0.52803(11) 1.0 0.0250(5) . . O2 O Uani 0.04471(6) 0.0412(2) 0.44658(13) 1.0 0.0383(6) . . N1 N Uani 0.16507(5) 0.3069(2) 0.40815(13) 1.0 0.0196(6) . . N2 N Uani 0.14764(5) 0.3478(2) 0.55609(13) 1.0 0.0216(6) . . N3 N Uani 0.16771(6) 0.0457(2) 0.50684(13) 1.0 0.0233(6) . . N4 N Uani 0.11681(6) 0.0578(2) 0.37295(13) 1.0 0.0232(6) . . N5 N Uani 0.08808(5) 0.3280(2) 0.42049(13) 1.0 0.0214(6) . . C1 C Uani 0.17650(7) 0.2664(3) 0.33831(16) 1.0 0.0229(7) . . C2 C Uani 0.19894(7) 0.3529(3) 0.30173(16) 1.0 0.0261(8) . . C3 C Uani 0.21076(7) 0.4863(3) 0.33852(16) 1.0 0.0252(8) . . C4 C Uani 0.20028(6) 0.5271(3) 0.41129(16) 1.0 0.0235(7) . . C5 C Uani 0.17756(6) 0.4360(3) 0.44467(15) 1.0 0.0216(7) . . C6 C Uani 0.16402(7) 0.4760(3) 0.52160(17) 1.0 0.0269(8) . . C7 C Uani 0.17019(7) 0.2940(3) 0.63742(16) 1.0 0.0294(8) . . C8 C Uani 0.20071(7) 0.1922(3) 0.62691(17) 1.0 0.0295(8) . . C9 C Uani 0.18644(7) 0.0414(3) 0.59690(17) 1.0 0.0302(8) . . C10 C Uani 0.15056(7) -0.0979(3) 0.47973(18) 1.0 0.0283(8) . . C11 C Uani 0.12829(7) -0.0803(3) 0.39263(17) 1.0 0.0265(8) . . C12 C Uani 0.12014(7) -0.1931(3) 0.3350(2) 1.0 0.0343(9) . . C13 C Uani 0.10033(8) -0.1641(3) 0.2555(2) 1.0 0.0367(9) . . C14 C Uani 0.08959(7) -0.0205(3) 0.23423(18) 1.0 0.0338(9) . . C15 C Uani 0.09796(7) 0.0869(3) 0.29466(17) 1.0 0.0282(8) . . C16 C Uani 0.08544(7) 0.4436(3) 0.36793(16) 1.0 0.0248(8) . . C17 C Uani 0.05359(7) 0.5228(3) 0.34362(18) 1.0 0.0314(8) . . C18 C Uani 0.02332(7) 0.4825(3) 0.37414(18) 1.0 0.0320(8) . . C19 C Uani 0.02564(7) 0.3630(3) 0.42690(18) 1.0 0.0310(8) . . C20 C Uani 0.05834(7) 0.2873(3) 0.44845(17) 1.0 0.0254(8) . . C21 C Uani 0.06353(7) 0.1500(3) 0.50029(19) 1.0 0.0304(8) . . C22 C Uani 0.04296(10) -0.0961(3) 0.4887(2) 1.0 0.0499(11) . . N7 N Uani 0.000 0.8142(5) 0.25000 1.000 0.086(2) . . C23 C Uani 0.000 0.9399(5) 0.25000 1.000 0.0511(18) . . C24 C Uani 0.000 1.0993(5) 0.25000 1.000 0.0387(12) . . Cl1 Cl Uani 0.08839(2) 0.40624(10) 0.13549(5) 1.0 0.0504(3) . . O3 O Uani 0.06026(5) 0.3238(2) 0.15909(13) 1.0 0.0368(7) . . O4 O Uani 0.08841(8) 0.4048(4) 0.05213(17) 1.0 0.0892(13) . . O5A O Uani 0.06998(17) 0.5636(4) 0.1281(3) 0.593(6) 0.078(2) . . O6A O Uani 0.11740(18) 0.4176(11) 0.1961(5) 0.593(6) 0.101(3) . . O5B O Uani 0.1108(3) 0.4985(8) 0.1940(6) 0.407(6) 0.054(3) . . O6B O Uani 0.11926(14) 0.2749(6) 0.1403(4) 0.407(6) 0.049(2) . . Cl2 Cl Uani 0.26521(2) 0.43644(7) 0.13258(4) 1.0 0.0259(2) . . O7 O Uani 0.26464(5) 0.5270(2) 0.05931(12) 1.0 0.0331(6) . . O8 O Uani 0.25443(6) 0.5236(2) 0.19628(13) 1.0 0.0406(7) . . O9 O Uani 0.24024(6) 0.3159(2) 0.11052(15) 1.0 0.0441(7) . . O10 O Uani 0.30145(5) 0.3815(2) 0.16266(13) 1.0 0.0395(7) . . H1 H Uiso 0.16876 0.17457 0.31343 1.0 0.0275 . . H2 H Uiso 0.20617 0.32164 0.25225 1.0 0.0314 . . H3 H Uiso 0.22584 0.54865 0.31399 1.0 0.0303 . . H4 H Uiso 0.20859 0.61678 0.43817 1.0 0.0282 . . H6 H Uiso 0.18450 0.51433 0.56459 1.0 0.0322 . . H6' H Uiso 0.14558 0.55466 0.50776 1.0 0.0322 . . H7 H Uiso 0.15416 0.24189 0.66868 1.0 0.0352 . . H7' H Uiso 0.18074 0.37942 0.67135 1.0 0.0352 . . H8 H Uiso 0.21825 0.18250 0.68108 1.0 0.0354 . . H8' H Uiso 0.21376 0.23505 0.586 1.000 0.0354 . . H9 H Uiso 0.20695 -0.02882 0.60453 1.0 0.0362 . . H9' H Uiso 0.16919 0.00714 0.63088 1.0 0.0362 . . H10 H Uiso 0.13484 -0.12904 0.51807 1.0 0.0339 . . H10' H Uiso 0.16954 -0.17342 0.48057 1.0 0.0339 . . H12 H Uiso 0.12815 -0.28999 0.35016 1.0 0.0410 . . H13 H Uiso 0.09412 -0.24097 0.21581 1.0 0.0440 . . H14 H Uiso 0.07676 0.00296 0.17928 1.0 0.0405 . . H15 H Uiso 0.09023 0.18458 0.28077 1.0 0.0338 . . H16 H Uiso 0.10616 0.47152 0.34696 1.0 0.0298 . . H17 H Uiso 0.05247 0.60362 0.30653 1.0 0.0377 . . H18 H Uiso 0.00128 0.53630 0.35901 1.0 0.0384 . . H19 H Uiso 0.00515 0.33298 0.44814 1.0 0.0371 . . H21 H Uiso 0.05193 0.16235 0.54954 1.0 0.0365 . . H22 H Uiso 0.06757 -0.13599 0.50687 1.0 0.0747 . . H23' H Uiso 0.02797 -0.16531 0.45029 1.0 0.0747 . . H31 H Uiso 0.12648 0.38381 0.56965 1.0 0.0259 . . H32 H Uiso 0.18595 0.05843 0.47694 1.0 0.0280 . . H222 H Uiso 0.03216 -0.08061 0.53751 1.0 0.0747 . . H24 H Uiso -0.01852 1.13511 0.27920 0.5 0.0578 . . H24' H Uiso -0.00546 1.13511 0.19219 0.5 0.0578 . . H24" H Uiso 0.02399 1.13511 0.27862 0.5 0.0578 . . 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 Fe1 0.0167(2) 0.0190(2) 0.0218(2) 0.0019(1) 0.0036(1) -0.0003(1) O1 0.0175(8) 0.0277(9) 0.0296(10) 0.0074(7) 0.0044(7) 0.0005(7) O2 0.0362(11) 0.0329(10) 0.0434(12) 0.0043(9) 0.0029(9) -0.0059(9) N1 0.0166(10) 0.0204(9) 0.0213(10) 0.0026(8) 0.0028(8) 0.0015(8) N2 0.0175(10) 0.0242(10) 0.0232(11) 0.0000(8) 0.0049(8) -0.0002(8) N3 0.0206(10) 0.0236(10) 0.0258(11) 0.0054(9) 0.0053(9) 0.0010(8) N4 0.0197(10) 0.0210(10) 0.0293(12) -0.0006(9) 0.0058(9) -0.0017(8) N5 0.0181(10) 0.0213(10) 0.0235(11) -0.0007(8) 0.0012(8) -0.0010(8) C1 0.0222(12) 0.0224(12) 0.0238(13) 0.0004(10) 0.0041(10) 0.0022(10) C2 0.0228(13) 0.0341(14) 0.0223(13) 0.0024(11) 0.0065(10) 0.0039(10) C3 0.0185(12) 0.0296(13) 0.0277(14) 0.0097(10) 0.0051(10) -0.0001(10) C4 0.0172(12) 0.0236(12) 0.0285(14) 0.0023(10) 0.0019(10) -0.0005(9) C5 0.0183(12) 0.0225(11) 0.0230(13) 0.0029(10) 0.0021(10) 0.0024(9) C6 0.0265(13) 0.0267(12) 0.0288(14) -0.0048(10) 0.0089(11) -0.0066(10) C7 0.0256(13) 0.0410(15) 0.0204(13) 0.0014(11) 0.0023(11) 0.0036(11) C8 0.0224(13) 0.0394(15) 0.0246(14) 0.0043(11) 0.0005(11) 0.0024(11) C9 0.0259(14) 0.0347(14) 0.0289(14) 0.0113(11) 0.0034(11) 0.0055(11) C10 0.0257(14) 0.0195(12) 0.0411(16) 0.0047(11) 0.0105(12) 0.0034(10) C11 0.0195(12) 0.0234(12) 0.0394(16) 0.0006(11) 0.0127(11) -0.0024(10) C12 0.0250(14) 0.0219(13) 0.058(2) -0.0065(12) 0.0136(13) -0.0033(10) C13 0.0255(14) 0.0360(15) 0.0506(19) -0.0181(13) 0.0129(13) -0.0074(12) C14 0.0262(14) 0.0406(15) 0.0334(16) -0.0093(12) 0.0038(12) -0.0048(12) C15 0.0252(13) 0.0290(13) 0.0298(14) -0.0013(11) 0.0043(11) -0.0020(10) C16 0.0234(13) 0.0223(12) 0.0270(14) 0.0020(10) 0.0013(10) -0.0019(10) C17 0.0293(14) 0.0230(12) 0.0386(16) 0.0052(11) -0.0001(12) 0.0004(11) C18 0.0226(13) 0.0285(13) 0.0399(16) 0.0007(12) -0.0047(12) 0.0045(11) C19 0.0188(12) 0.0308(14) 0.0419(16) 0.0019(12) 0.0032(12) -0.0015(11) C20 0.0184(12) 0.0278(13) 0.0283(14) -0.0005(10) 0.0009(10) -0.0023(10) C21 0.0178(12) 0.0329(14) 0.0398(16) 0.0070(12) 0.0045(11) -0.0021(11) C22 0.0469(19) 0.0342(16) 0.063(2) 0.0122(15) -0.0012(17) -0.0119(14) N7 0.047(3) 0.037(2) 0.158(6) 0.00 -0.015(3) 0.0000 C23 0.025(2) 0.045(3) 0.075(4) 0.00 -0.008(2) 0.0000 C24 0.034(2) 0.039(2) 0.039(2) 0.00 -0.0014(19) 0.0000 Cl1 0.0587(5) 0.0629(5) 0.0315(4) -0.0026(3) 0.0136(4) -0.0389(4) O3 0.0247(10) 0.0405(11) 0.0468(13) 0.0135(9) 0.0114(9) -0.0018(8) O4 0.070(2) 0.150(3) 0.0457(16) 0.0248(18) 0.0083(14) -0.049(2) O5A 0.137(5) 0.0208(19) 0.065(3) 0.0051(19) -0.001(3) -0.016(2) O6A 0.045(3) 0.173(9) 0.068(4) 0.063(6) -0.027(3) -0.059(5) O5B 0.069(6) 0.045(4) 0.058(5) -0.022(4) 0.034(4) -0.031(4) O6B 0.026(3) 0.050(4) 0.077(5) -0.019(3) 0.025(3) 0.003(2) Cl2 0.0202(3) 0.0292(3) 0.0296(3) 0.0031(2) 0.0080(3) 0.0031(2) O7 0.0289(10) 0.0449(11) 0.0257(10) 0.0045(8) 0.0063(8) -0.0052(9) O8 0.0523(13) 0.0403(11) 0.0361(12) 0.0066(9) 0.0250(10) 0.0124(10) O9 0.0339(12) 0.0331(11) 0.0624(15) 0.0053(10) 0.0038(10) -0.0047(9) O10 0.0234(10) 0.0501(12) 0.0446(12) 0.0046(10) 0.0063(9) 0.0122(9) #=============================================================================== # 10. MOLECULAR GEOMETRY _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 Fe1 O1 1.8369(17) . . yes Fe1 N1 2.011(2) . . yes Fe1 N2 2.013(2) . . yes Fe1 N3 1.998(2) . . yes Fe1 N4 1.970(2) . . yes Fe1 N5 1.988(2) . . yes Cl1 O5B 1.412(9) . . yes Cl1 O6B 1.659(6) . . yes Cl1 O5A 1.587(4) . . yes Cl1 O3 1.416(2) . . yes Cl1 O4 1.363(3) . . yes Cl1 O6A 1.313(8) . . yes Cl2 O7 1.452(2) . . yes Cl2 O8 1.435(2) . . yes Cl2 O9 1.441(2) . . yes Cl2 O10 1.437(2) . . yes O1 C21 1.392(3) . . yes O2 C21 1.412(3) . . yes O2 C22 1.438(3) . . yes N1 C1 1.354(3) . . yes N1 C5 1.359(3) . . yes N2 C6 1.487(3) . . yes N2 C7 1.500(3) . . yes N3 C9 1.492(3) . . yes N3 C10 1.486(3) . . yes N4 C11 1.349(3) . . yes N4 C15 1.352(3) . . yes N5 C16 1.351(3) . . yes N5 C20 1.347(3) . . yes N2 H31 0.93 . . no N3 H32 0.93 . . no N7 C23 1.147(6) . . yes C1 C2 1.381(4) . . no C2 C3 1.388(4) . . no C3 C4 1.381(4) . . no C4 C5 1.384(4) . . no C5 C6 1.499(4) . . no C7 C8 1.514(4) . . no C8 C9 1.520(4) . . no C10 C11 1.500(4) . . no C11 C12 1.385(4) . . no C12 C13 1.380(4) . . no C13 C14 1.393(4) . . no C14 C15 1.380(4) . . no C16 C17 1.383(4) . . no C17 C18 1.386(4) . . no C18 C19 1.382(4) . . no C19 C20 1.389(4) . . no C20 C21 1.502(4) . . no C1 H1 0.95 . . no C2 H2 0.95 . . no C3 H3 0.95 . . no C4 H4 0.95 . . no C6 H6 0.99 . . no C6 H6' 0.99 . . no C7 H7 0.99 . . no C7 H7' 0.99 . . no C8 H8' 0.99 . . no C8 H8 0.99 . . no C9 H9 0.99 . . no C9 H9' 0.99 . . no C10 H10' 0.99 . . no C10 H10 0.99 . . no C12 H12 0.95 . . no C13 H13 0.95 . . no C14 H14 0.95 . . no C15 H15 0.95 . . no C16 H16 0.95 . . no C17 H17 0.95 . . no C18 H18 0.95 . . no C19 H19 0.95 . . no C21 H21 1.00 . . no C22 H222 0.98 . . no C22 H22 0.98 . . no C22 H23' 0.98 . . no C23 C24 1.454(6) . . no C24 H24" 0.98 . . no C24 H24' 0.98 . . no C24 H24" 0.98 . 2_555 no C24 H24 0.98 . 2_555 no C24 H24' 0.98 . 2_555 no C24 H24 0.98 . . 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 O1 Fe1 N1 172.72(8) . . . yes O1 Fe1 N2 89.87(8) . . . yes O1 Fe1 N3 89.87(8) . . . yes O1 Fe1 N4 94.21(8) . . . yes O1 Fe1 N5 84.45(8) . . . yes N1 Fe1 N2 82.86(8) . . . yes N1 Fe1 N3 91.34(8) . . . yes N1 Fe1 N4 93.06(9) . . . yes N1 Fe1 N5 95.09(8) . . . yes N2 Fe1 N3 97.32(8) . . . yes N2 Fe1 N4 175.71(9) . . . yes N2 Fe1 N5 88.98(8) . . . yes N3 Fe1 N4 81.39(8) . . . yes N3 Fe1 N5 171.52(8) . . . yes N4 Fe1 N5 92.73(9) . . . yes O5B Cl1 O6B 95.0(4) . . . yes O3 Cl1 O5B 120.3(4) . . . yes O3 Cl1 O6B 99.1(2) . . . yes O4 Cl1 O5A 91.4(2) . . . yes O4 Cl1 O6A 125.4(4) . . . yes O3 Cl1 O4 115.20(17) . . . yes O3 Cl1 O5A 99.3(2) . . . yes O3 Cl1 O6A 112.7(4) . . . yes O5A Cl1 O6A 105.4(5) . . . yes O4 Cl1 O5B 123.8(4) . . . yes O4 Cl1 O6B 83.8(3) . . . yes O7 Cl2 O8 109.05(11) . . . yes O7 Cl2 O9 109.43(13) . . . yes O7 Cl2 O10 109.16(12) . . . yes O8 Cl2 O9 109.59(13) . . . yes O9 Cl2 O10 109.85(12) . . . yes O8 Cl2 O10 109.74(13) . . . yes Fe1 O1 C21 114.94(16) . . . yes C21 O2 C22 112.5(2) . . . yes C1 N1 C5 117.7(2) . . . yes Fe1 N1 C1 127.64(17) . . . yes Fe1 N1 C5 114.62(16) . . . yes C6 N2 C7 113.06(19) . . . yes Fe1 N2 C6 110.07(16) . . . yes Fe1 N2 C7 117.88(15) . . . yes C9 N3 C10 110.83(19) . . . yes Fe1 N3 C9 120.35(16) . . . yes Fe1 N3 C10 106.75(16) . . . yes Fe1 N4 C11 114.34(17) . . . yes Fe1 N4 C15 126.54(17) . . . yes C11 N4 C15 119.1(2) . . . yes Fe1 N5 C16 129.80(17) . . . yes Fe1 N5 C20 111.73(16) . . . yes C16 N5 C20 118.5(2) . . . yes C7 N2 H31 105 . . . no C6 N2 H31 105 . . . no Fe1 N2 H31 105 . . . no Fe1 N3 H32 106 . . . no C10 N3 H32 106 . . . no C9 N3 H32 106 . . . no N1 C1 C2 122.8(2) . . . yes C1 C2 C3 118.8(2) . . . no C2 C3 C4 119.1(2) . . . no C3 C4 C5 119.4(2) . . . no N1 C5 C4 122.1(2) . . . yes C4 C5 C6 122.2(2) . . . no N1 C5 C6 115.7(2) . . . yes N2 C6 C5 111.6(2) . . . yes N2 C7 C8 113.6(2) . . . yes C7 C8 C9 111.6(2) . . . no N3 C9 C8 110.8(2) . . . yes N3 C10 C11 108.0(2) . . . yes N4 C11 C12 121.2(2) . . . yes C10 C11 C12 124.4(3) . . . no N4 C11 C10 114.4(2) . . . yes C11 C12 C13 119.7(3) . . . no C12 C13 C14 119.1(3) . . . no C13 C14 C15 118.6(3) . . . no N4 C15 C14 122.2(2) . . . yes N5 C16 C17 122.2(2) . . . yes C16 C17 C18 119.0(3) . . . no C17 C18 C19 119.1(3) . . . no C18 C19 C20 119.1(3) . . . no N5 C20 C21 113.8(2) . . . yes C19 C20 C21 124.1(2) . . . no N5 C20 C19 122.1(2) . . . yes O2 C21 C20 104.3(2) . . . yes O1 C21 C20 111.0(2) . . . yes O1 C21 O2 112.9(2) . . . yes N1 C1 H1 119 . . . no C2 C1 H1 119 . . . no C1 C2 H2 121 . . . no C3 C2 H2 121 . . . no C4 C3 H3 120 . . . no C2 C3 H3 120 . . . no C3 C4 H4 120 . . . no C5 C4 H4 120 . . . no N2 C6 H6' 109 . . . no N2 C6 H6 109 . . . no H6 C6 H6' 108 . . . no C5 C6 H6 109 . . . no C5 C6 H6' 109 . . . no N2 C7 H7 109 . . . no C8 C7 H7' 109 . . . no N2 C7 H7' 109 . . . no C8 C7 H7 109 . . . no H7 C7 H7' 108 . . . no C7 C8 H8 109 . . . no C7 C8 H8' 109 . . . no C9 C8 H8 109 . . . no C9 C8 H8' 109 . . . no H8 C8 H8' 108 . . . no N3 C9 H9 109 . . . no N3 C9 H9' 110 . . . no C8 C9 H9 109 . . . no C8 C9 H9' 109 . . . no H9 C9 H9' 108 . . . no N3 C10 H10 110 . . . no N3 C10 H10' 110 . . . no C11 C10 H10 110 . . . no C11 C10 H10' 110 . . . no H10 C10 H10' 108 . . . no C11 C12 H12 120 . . . no C13 C12 H12 120 . . . no C12 C13 H13 120 . . . no C14 C13 H13 120 . . . no C15 C14 H14 121 . . . no C13 C14 H14 121 . . . no N4 C15 H15 119 . . . no C14 C15 H15 119 . . . no N5 C16 H16 119 . . . no C17 C16 H16 119 . . . no C18 C17 H17 120 . . . no C16 C17 H17 121 . . . no C17 C18 H18 120 . . . no C19 C18 H18 120 . . . no C20 C19 H19 120 . . . no C18 C19 H19 120 . . . no O2 C21 H21 109 . . . no C20 C21 H21 109 . . . no O1 C21 H21 109 . . . no O2 C22 H22 109 . . . no O2 C22 H23' 109 . . . no H22 C22 H23' 109 . . . no H22 C22 H222 110 . . . no O2 C22 H222 109 . . . no H23' C22 H222 109 . . . no N7 C23 C24 180.00(1) . . . yes H24' C24 H24" 56 2_555 . . no H24" C24 H24" 141 . . 2_555 no H24 C24 H24" 109 2_555 . 2_555 no H24' C24 H24" 109 2_555 . 2_555 no H24 C24 H24' 109 2_555 . 2_555 no H24 C24 H24" 109 . . . no H24 C24 H24 141 . . 2_555 no H24 C24 H24' 56 . . 2_555 no H24 C24 H24" 56 . . 2_555 no H24' C24 H24" 109 . . . no H24 C24 H24' 56 2_555 . . no H24' C24 H24' 141 . . 2_555 no H24' C24 H24" 56 . . 2_555 no H24 C24 H24" 56 2_555 . . no C23 C24 H24 109 . . . no C23 C24 H24' 109 . . . no C23 C24 H24" 109 . . . no C23 C24 H24 109 . . 2_555 no C23 C24 H24' 109 . . 2_555 no C23 C24 H24" 109 . . 2_555 no H24 C24 H24' 109 . . . 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 N2 Fe1 O1 C21 105.65(17) . . . . no N3 Fe1 O1 C21 -157.03(18) . . . . no N4 Fe1 O1 C21 -75.68(18) . . . . no N5 Fe1 O1 C21 16.67(17) . . . . no N2 Fe1 N1 C1 169.3(2) . . . . no N2 Fe1 N1 C5 -11.84(17) . . . . no N3 Fe1 N1 C1 72.1(2) . . . . no N3 Fe1 N1 C5 -109.05(17) . . . . no N4 Fe1 N1 C1 -9.4(2) . . . . no N4 Fe1 N1 C5 169.51(17) . . . . no N5 Fe1 N1 C1 -102.4(2) . . . . no N5 Fe1 N1 C5 76.49(17) . . . . no O1 Fe1 N2 C6 -160.03(16) . . . . no O1 Fe1 N2 C7 68.29(17) . . . . no N1 Fe1 N2 C6 19.68(15) . . . . no N1 Fe1 N2 C7 -112.00(17) . . . . no N3 Fe1 N2 C6 110.12(16) . . . . no N3 Fe1 N2 C7 -21.56(18) . . . . no N5 Fe1 N2 C6 -75.58(16) . . . . no N5 Fe1 N2 C7 152.74(17) . . . . no O1 Fe1 N3 C9 -66.54(19) . . . . no O1 Fe1 N3 C10 60.80(16) . . . . no N1 Fe1 N3 C9 106.28(19) . . . . no N1 Fe1 N3 C10 -126.37(16) . . . . no N2 Fe1 N3 C9 23.31(19) . . . . no N2 Fe1 N3 C10 150.65(16) . . . . no N4 Fe1 N3 C9 -160.8(2) . . . . no N4 Fe1 N3 C10 -33.48(16) . . . . no O1 Fe1 N4 C11 -68.31(19) . . . . no O1 Fe1 N4 C15 112.3(2) . . . . no N1 Fe1 N4 C11 111.82(19) . . . . no N1 Fe1 N4 C15 -67.6(2) . . . . no N3 Fe1 N4 C11 20.92(19) . . . . no N3 Fe1 N4 C15 -158.5(2) . . . . no N5 Fe1 N4 C11 -152.93(19) . . . . no N5 Fe1 N4 C15 27.6(2) . . . . no O1 Fe1 N5 C16 174.4(2) . . . . no O1 Fe1 N5 C20 -6.33(17) . . . . no N1 Fe1 N5 C16 1.7(2) . . . . no N1 Fe1 N5 C20 -179.04(18) . . . . no N2 Fe1 N5 C16 84.4(2) . . . . no N2 Fe1 N5 C20 -96.30(18) . . . . no N4 Fe1 N5 C16 -91.7(2) . . . . no N4 Fe1 N5 C20 87.64(18) . . . . no Fe1 O1 C21 O2 94.0(2) . . . . no Fe1 O1 C21 C20 -22.8(3) . . . . no C22 O2 C21 O1 66.3(3) . . . . no C22 O2 C21 C20 -173.1(2) . . . . no Fe1 N1 C1 C2 176.36(19) . . . . no C5 N1 C1 C2 -2.5(4) . . . . no Fe1 N1 C5 C4 -176.95(19) . . . . no Fe1 N1 C5 C6 0.8(3) . . . . no C1 N1 C5 C4 2.0(4) . . . . no C1 N1 C5 C6 179.8(2) . . . . no Fe1 N2 C6 C5 -24.2(2) . . . . no C7 N2 C6 C5 109.9(2) . . . . no Fe1 N2 C7 C8 47.3(3) . . . . no C6 N2 C7 C8 -83.1(3) . . . . no Fe1 N3 C9 C8 -48.9(3) . . . . no C10 N3 C9 C8 -174.3(2) . . . . no Fe1 N3 C10 C11 40.0(2) . . . . no C9 N3 C10 C11 172.7(2) . . . . no Fe1 N4 C11 C10 -2.5(3) . . . . no Fe1 N4 C11 C12 178.5(2) . . . . no C15 N4 C11 C10 177.0(2) . . . . no C15 N4 C11 C12 -2.0(4) . . . . no Fe1 N4 C15 C14 -179.7(2) . . . . no C11 N4 C15 C14 0.9(4) . . . . no Fe1 N5 C16 C17 -179.3(2) . . . . no C20 N5 C16 C17 1.5(4) . . . . no Fe1 N5 C20 C19 178.6(2) . . . . no Fe1 N5 C20 C21 -4.4(3) . . . . no C16 N5 C20 C19 -2.0(4) . . . . no C16 N5 C20 C21 175.0(2) . . . . no N1 C1 C2 C3 0.9(4) . . . . no C1 C2 C3 C4 1.2(4) . . . . no C2 C3 C4 C5 -1.6(4) . . . . no C3 C4 C5 N1 0.0(4) . . . . no C3 C4 C5 C6 -177.7(2) . . . . no N1 C5 C6 N2 15.7(3) . . . . no C4 C5 C6 N2 -166.5(2) . . . . no N2 C7 C8 C9 -74.2(3) . . . . no C7 C8 C9 N3 73.6(3) . . . . no N3 C10 C11 N4 -25.3(3) . . . . no N3 C10 C11 C12 153.6(3) . . . . no N4 C11 C12 C13 0.9(4) . . . . no C10 C11 C12 C13 -178.0(3) . . . . no C11 C12 C13 C14 1.4(4) . . . . no C12 C13 C14 C15 -2.5(4) . . . . no C13 C14 C15 N4 1.4(4) . . . . no N5 C16 C17 C18 0.0(4) . . . . no C16 C17 C18 C19 -1.0(4) . . . . no C17 C18 C19 C20 0.5(4) . . . . no C18 C19 C20 N5 1.0(4) . . . . no C18 C19 C20 C21 -175.6(3) . . . . no N5 C20 C21 O1 17.2(3) . . . . no N5 C20 C21 O2 -104.8(3) . . . . no C19 C20 C21 O1 -166.0(3) . . . . no C19 C20 C21 O2 72.1(3) . . . . no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag Fe1 H8' 3.35 . . no Cl1 H31 2.74 . 4_564 no Cl1 H15 3.11 . . no Cl2 H32 3.03 . 6_555 no Cl2 H6 3.04 . 4_564 no O1 N2 2.722(3) . . no O1 C9 3.271(3) . . no O1 C10 2.953(3) . . no O1 N3 2.711(3) . . no O1 C20 2.385(3) . . no O1 N5 2.573(3) . . no O1 C11 3.206(3) . . no O1 C7 3.268(3) . . no O1 N4 2.790(3) . . no O2 N5 3.160(3) . . no O2 C24 3.340(2) . 1_545 no O2 C24 3.340(2) . 2_545 no O2 N4 3.194(3) . . no O3 C15 3.204(3) . . no O3 C18 3.398(3) . 2_555 no O3 C19 3.258(3) . 2_555 no O4 C20 3.352(4) . 4_564 no O4 C6 3.180(4) . 4_564 no O4 C22 3.343(5) . 4_554 no O4 N2 3.162(4) . 4_564 no O4 N5 3.250(4) . 4_564 no O4 C16 3.295(4) . 4_564 no O5A C13 3.288(5) . 1_565 no O5A C20 3.182(5) . 4_564 no O5A C21 3.323(5) . 4_564 no O5B C7 3.209(10) . 4_564 no O5B C13 3.288(8) . 1_565 no O5B N2 3.208(10) . 4_564 no O5B C16 3.224(10) . . no O6A C16 3.290(8) . . no O6A C1 3.172(9) . . no O6A C2 3.239(8) . . no O6B C14 3.405(6) . . no O6B C15 3.288(7) . . no O7 N3 2.972(3) . 6_555 no O7 C4 3.079(3) . 4_564 no O7 C1 3.302(3) . 6_555 no O8 C3 3.136(3) . . no O8 C2 3.358(3) . . no O8 C8 3.335(3) . 4_564 no O10 C11 2.988(3) . 6_555 no O10 C12 3.018(3) . 6_555 no O10 C10 3.239(3) . 6_555 no O1 H31 2.65 . . no O1 H22 2.62 . . no O1 H10 2.63 . . no O2 H24" 2.82 . 1_545 no O2 H24' 2.58 . 2_545 no O3 H19 2.70 . 2_555 no O3 H15 2.43 . . no O3 H24 2.67 . 2_545 no O4 H6' 2.44 . 4_564 no O4 H22 2.63 . 4_554 no O4 H31 2.38 . 4_564 no O5A H18 2.74 . 2_555 no O5A H31 2.55 . 4_564 no O5A H13 2.35 . 1_565 no O5A H21 2.83 . 4_564 no O5B H16 2.56 . . no O5B H13 2.50 . 1_565 no O5B H31 2.48 . 4_564 no O6A H15 2.84 . . no O6A H16 2.64 . . no O6A H31 2.82 . 4_564 no O6B H22 2.89 . 4_554 no O6B H15 2.86 . . no O6B H10 2.57 . 4_554 no O7 H4 2.88 . 4_564 no O7 H32 2.09 . 6_555 no O8 H7' 2.85 . 4_564 no O8 H3 2.41 . . no O8 H2 2.87 . . no O8 H8 2.78 . 7_556 no O9 H2 2.88 . . no O9 H4 2.88 . 4_564 no O9 H6 2.59 . 4_564 no O9 H9 2.90 . 4_554 no O9 H3 2.90 . 6_545 no O9 H4 2.88 . 6_545 no O10 H10' 2.83 . 6_555 no O10 H32 2.92 . 6_555 no O10 H8 2.87 . 7_556 no O10 H1 2.89 . 6_555 no O10 H4 2.90 . 6_545 no N1 C15 3.443(3) . . no N1 N5 2.950(3) . . no N1 C6 2.420(3) . . no N1 N2 2.663(3) . . no N1 N3 2.868(3) . . no N1 N4 2.889(3) . . no N1 C16 3.181(3) . . no N2 N3 3.012(3) . . no N2 N5 2.804(3) . . no N2 N1 2.663(3) . . no N2 O5B 3.208(10) . 4_565 no N2 O1 2.722(3) . . no N2 C5 2.470(3) . . no N2 C9 3.159(3) . . no N2 O4 3.162(4) . 4_565 no N3 O7 2.972(3) . 6_545 no N3 N2 3.012(3) . . no N3 C7 3.101(3) . . no N3 C11 2.415(3) . . no N3 N1 2.868(3) . . no N3 N4 2.587(3) . . no N3 O1 2.711(3) . . no N4 O2 3.194(3) . . no N4 O1 2.790(3) . . no N4 C20 3.448(3) . . no N4 N5 2.864(3) . . no N4 N1 2.889(3) . . no N4 N3 2.587(3) . . no N4 C1 3.085(3) . . no N4 C10 2.396(3) . . no N4 C21 3.290(4) . . no N5 C6 3.273(3) . . no N5 C5 3.447(3) . . no N5 N4 2.864(3) . . no N5 O2 3.160(3) . . no N5 C15 3.088(3) . . no N5 C21 2.388(3) . . no N5 O1 2.573(3) . . no N5 N1 2.950(3) . . no N5 O4 3.250(4) . 4_565 no N5 N2 2.804(3) . . no N1 H32 2.58 . . no N1 H16 2.69 . . no N4 H1 2.59 . . no N4 H32 2.79 . . no N5 H15 2.65 . . no N5 H31 2.61 . . no N7 H17 2.77 . . no N7 H17 2.77 . 2_555 no C1 C15 3.320(4) . . no C1 O6A 3.172(9) . . no C1 O7 3.302(3) . 6_545 no C2 O8 3.358(3) . . no C2 O6A 3.239(8) . . no C3 O8 3.136(3) . . no C4 O7 3.079(3) . 4_565 no C5 C16 3.426(4) . . no C6 O4 3.180(4) . 4_565 no C6 C16 3.462(4) . . no C7 O5B 3.209(10) . 4_565 no C8 O8 3.335(3) . 4_565 no C10 O10 3.239(3) . 6_545 no C11 O10 2.988(3) . 6_545 no C12 O10 3.018(3) . 6_545 no C13 O5B 3.288(8) . 1_545 no C13 O5A 3.288(5) . 1_545 no C14 C23 3.451(3) . 2_545 no C14 O6B 3.405(6) . . no C14 C23 3.451(3) . 1_545 no C15 C16 3.534(4) . . no C15 O6B 3.288(7) . . no C15 C1 3.320(4) . . no C15 O3 3.204(3) . . no C16 O6A 3.290(8) . . no C16 C5 3.426(4) . . no C16 O5B 3.224(10) . . no C16 C15 3.534(4) . . no C16 C6 3.462(4) . . no C16 O4 3.295(4) . 4_565 no C18 O3 3.398(3) . 2_555 no C19 O3 3.258(3) . 2_555 no C20 O4 3.352(4) . 4_565 no C20 O5A 3.182(5) . 4_565 no C21 O5A 3.323(5) . 4_565 no C22 O4 3.343(5) . 4_555 no C23 C14 3.451(3) . 2_565 no C23 C14 3.451(3) . 1_565 no C24 O2 3.340(2) . 1_565 no C24 O2 3.340(2) . 2_565 no C1 H32 2.92 . . no C2 H8 3.08 . 7_556 no C3 H9 3.06 . 7_556 no C3 H7' 2.99 . 4_564 no C5 H16 2.84 . . no C5 H8' 3.04 . . no C6 H8' 2.93 . . no C13 H7 2.80 . 4_554 no C13 H17 3.01 . 1_545 no C14 H24 2.99 . 2_545 no C14 H24" 3.06 . 1_545 no C15 H1 2.73 . . no C15 H24 3.01 . 2_545 no C15 H24" 2.77 . 1_545 no C16 H6' 3.03 . . no C16 H12 2.96 . 1_565 no C16 H15 2.79 . . no C19 H24' 2.84 . 2_545 no C20 H31 3.02 . . no C20 H24' 3.04 . 2_545 no H1 N4 2.59 . . no H1 O10 2.89 . 6_545 no H1 C15 2.73 . . no H2 O8 2.87 . . no H2 O9 2.88 . . no H3 O9 2.90 . 6_555 no H3 O8 2.41 . . no H4 O9 2.88 . 6_555 no H4 O10 2.90 . 6_555 no H4 H6 2.60 . . no H4 H10' 2.59 . 1_565 no H4 O7 2.88 . 4_565 no H4 O9 2.88 . 4_565 no H6 Cl2 3.04 . 4_565 no H6 O9 2.59 . 4_565 no H6 H7' 2.16 . . no H6 H4 2.60 . . no H6' O4 2.44 . 4_565 no H6' C16 3.03 . . no H7 H9' 2.33 . . no H7 H13 2.53 . 4_555 no H7 C13 2.80 . 4_555 no H7' C3 2.99 . 4_565 no H7' O8 2.85 . 4_565 no H7' H6 2.16 . . no H8 O10 2.87 . 7_556 no H8 C2 3.08 . 7_556 no H8 O8 2.78 . 7_556 no H8' C6 2.93 . . no H8' H32 2.47 . . no H8' C5 3.04 . . no H8' Fe1 3.35 . . no H9 H10' 2.57 . . no H9 C3 3.06 . 7_556 no H9 O9 2.90 . 4_555 no H9' H7 2.33 . . no H9' H10 2.37 . . no H10 O1 2.63 . . no H10 O6B 2.57 . 4_555 no H10 H22 2.50 . . no H10 H9' 2.37 . . no H10' H9 2.57 . . no H10' H12 2.59 . . no H10' O10 2.83 . 6_545 no H10' H4 2.59 . 1_545 no H12 C16 2.96 . 1_545 no H12 H16 2.32 . 1_545 no H12 H10' 2.59 . . no H13 O5B 2.50 . 1_545 no H13 O5A 2.35 . 1_545 no H13 H7 2.53 . 4_554 no H15 O3 2.43 . . no H15 Cl1 3.11 . . no H15 C16 2.79 . . no H15 O6A 2.84 . . no H15 N5 2.65 . . no H15 H24" 2.52 . 1_545 no H15 O6B 2.86 . . no H16 O5B 2.56 . . no H16 H12 2.32 . 1_565 no H16 C5 2.84 . . no H16 O6A 2.64 . . no H16 N1 2.69 . . no H17 C13 3.01 . 1_565 no H17 N7 2.77 . . no H17 N7 2.77 . . no H18 O5A 2.74 . 2_555 no H19 O3 2.70 . 2_555 no H21 H222 2.33 . . no H21 O5A 2.83 . 4_565 no H22 O1 2.62 . . no H22 O6B 2.89 . 4_555 no H22 H10 2.50 . . no H22 O4 2.63 . 4_555 no H24 C14 2.99 . 2_565 no H24 O3 2.67 . 2_565 no H24 C15 3.01 . 2_565 no H24' O2 2.58 . 2_565 no H24' C19 2.84 . 2_565 no H24' C20 3.04 . 2_565 no H24" C14 3.06 . 1_565 no H24" H15 2.52 . 1_565 no H24" C15 2.77 . 1_565 no H24" O2 2.82 . 1_565 no H31 O6A 2.82 . 4_565 no H31 C20 3.02 . . no H31 Cl1 2.74 . 4_565 no H31 O4 2.38 . 4_565 no H31 O5B 2.48 . 4_565 no H31 O5A 2.55 . 4_565 no H32 H8' 2.47 . . no H32 Cl2 3.03 . 6_545 no H32 C1 2.92 . . no H32 O10 2.92 . 6_545 no H32 O7 2.09 . 6_545 no H222 H21 2.33 . . 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 # #D H A D - H H...A D...A D - H...A symm(A) # N2 H31 O4 0.9300 2.3800 3.162(4) 141 4_565 yes N2 H31 O5A 0.9300 2.5500 3.467(6) 168 4_565 yes N3 H32 O7 0.9300 2.0900 2.972(3) 159 6_545 yes C1 H1 N4 0.9500 2.5900 3.085(3) 113 . yes C3 H3 O8 0.9500 2.4100 3.136(3) 134 . yes C6 H6 O9 0.9900 2.5900 3.488(4) 151 4_565 yes C6 H6' O4 0.9900 2.4400 3.180(4) 131 4_565 yes C13 H13 O5A 0.9500 2.3500 3.288(5) 170 1_545 yes C15 H15 O3 0.9500 2.4300 3.204(3) 139 . yes C24 H24' O2 0.9800 2.5800 3.340(2) 135 2_565 yes #===END of Crystallographic Information File