# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 182 _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name _publ_author_address _publ_author_footnote 'Christian Serre' ; Institut Lavoisier, CNRS UMR 8180 Universite de Versailles St-Quentin-en-Yvelines 45, avenue des Etats-Unis 78035 Versailles, France ; . 'Tarek Baati' ; Institut Lavoisier, CNRS UMR 8180 Universite de Versailles St-Quentin-en-Yvelines 45, avenue des Etats-Unis 78035 Versailles, France ; . 'Jean-Marc Greneche' ; Institut Lavoisier, CNRS UMR 8180 Universite de Versailles St-Quentin-en-Yvelines 45, avenue des Etats-Unis 78035 Versailles, France ; . 'Daniela Heurtaux' '' '' 'Patricia Horcajada' '' '' 'Stuart R. Miller' '' '' _publ_contact_author_name 'Christian Serre' _publ_contact_author_address ; CNRS Versailles 78035 FRANCE ; _publ_contact_author_email SERRE@CHIMIE.UVSQ.FR _publ_contact_author_fax ? _publ_contact_author_phone 0033139254377 _publ_contact_letter ; Please consider this CIF for publication. I certify that this contibution is the original work of those listed as authors; that it has not been published before (in any language or medium) and is not being considered for publication elsewhere; that all authors concur with and are aware of the submission; that all workers involved in the study are listed as authors or given proper credit in the acknowledgements; that I have obtained permission for and acknowledged the source of any excerpts from other copyright works; and that to the best of my knowledge the paper contains no statements which are libellous, unlawful or in any way actionable. All coauthors have made significant scientific contributions to the work reported, including the ideas and their execution, and share responsibility and accountability for the results. ; _publ_requested_category ? _publ_section_title ; Biodegradable therapeutic MOFs for the delivery of bioactive molecules ; # Attachment 'Bio-MIl-1.cif' data_BioMIL-1 _database_code_depnum_ccdc_archive 'CCDC 775194' #TrackingRef 'Bio-MIl-1.cif' # start Validation Reply Form _vrf_PUBL006_GLOBAL ; PROBLEM: _publ_requested_journal is missing RESPONSE: ... ; _vrf_RINTA01_BioMIL-1 ; PROBLEM: The value of Rint is greater than 0.25 RESPONSE: this data was collected on the most cryustalline sample. Authors are are that the crystal quality is poor, however the materials could not be made more crystalline. ; _vrf_PLAT020_BioMIL-1 ; PROBLEM: The value of Rint is greater than 0.12 ......... 0.27 RESPONSE: Several datasets for different crystals and different samples were collected, with the dataset reported here being the best one. ; _vrf_PLAT026_BioMIL-1 ; PROBLEM: Ratio Observed / Unique Reflections too Low .... 25 Perc. RESPONSE: Several datasets for different crystals and different samples were collected, with the dataset reported here being the best one. ; _vrf_PLAT601_BioMIL-1 ; PROBLEM: Structure Contains Solvent Accessible VOIDS of . 391.00 A**3 RESPONSE: Structure has inaccessible cavities ; # end Validation Reply Form #Added by publCIF (CCDC output) (Thu 14. Jan 15:15:02 2010) _publ_section_related_literature ? _publ_section_abstract ; ? ; _audit_update_record ; 2010-01-14 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C32 H23 Fe3 N5 O13 ' _chemical_formula_sum 'C32 H23 Fe3 N5 O13 ' _chemical_formula_weight 853.10 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' 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.064(2) _cell_length_b 21.464(4) _cell_length_c 19.613(3) _cell_angle_alpha 90.00 _cell_angle_beta 122.479(8) _cell_angle_gamma 90.00 _cell_volume 3929.1(12) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5987 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 20.79 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas 1.497 _exptl_crystal_density_diffrn 1.424 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1710.93 _exptl_absorpt_coefficient_mu 1.156 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean - _diffrn_standards_number - _diffrn_standards_interval_count - _diffrn_standards_decay_% - _diffrn_reflns_number 29416 _diffrn_reflns_av_R_equivalents 0.2721 _diffrn_reflns_av_sigmaI/netI 0.4520 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 29.72 _reflns_number_total 11168 _reflns_number_gt 2737 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(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^)+(0.1424P)^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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0085(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 11059 _refine_ls_number_parameters 479 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.3186 _refine_ls_R_factor_gt 0.1038 _refine_ls_wR_factor_ref 0.3275 _refine_ls_wR_factor_gt 0.2396 _refine_ls_goodness_of_fit_ref 0.846 _refine_ls_restrained_S_all 0.846 _refine_ls_shift/su_max 0.009 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Fe1 Fe -0.48579(14) 0.25122(6) 0.00661(9) 0.0376(4) Uani 1 1 d . . . Fe2 Fe -0.30633(15) 0.36980(6) 0.12088(9) 0.0393(4) Uani 1 1 d . . . Fe3 Fe -0.29228(15) 0.23504(7) 0.20616(9) 0.0414(4) Uani 1 1 d . . . O1 O -0.3616(7) 0.2874(3) 0.1090(4) 0.0433(17) Uani 1 1 d . . . O2 O -0.6204(7) 0.3260(3) -0.0423(4) 0.053(2) Uani 1 1 d . . . O3 O -0.3717(7) 0.2856(3) -0.0414(4) 0.0489(19) Uani 1 1 d . . . O4 O -0.3890(7) 0.1679(3) 0.0222(4) 0.0495(19) Uani 1 1 d . . . O5 O -0.6266(7) 0.2151(3) 0.0345(5) 0.0523(19) Uani 1 1 d . . . O6 O -0.5054(7) 0.4059(3) 0.0412(4) 0.0462(18) Uani 1 1 d . . . O7 O -0.2737(8) 0.3728(3) 0.0288(4) 0.055(2) Uani 1 1 d . . . O8 O -1.0963(7) 0.1479(3) -0.3038(5) 0.058(2) Uani 1 1 d . . . O9 O -0.3310(9) 0.3937(3) 0.2124(5) 0.060(2) Uani 1 1 d . . . O10 O -0.5021(8) 0.2106(4) 0.1695(4) 0.059(2) Uani 1 1 d . . . O11 O -0.2726(8) 0.1509(3) 0.1564(5) 0.058(2) Uani 1 1 d . . . O12 O -1.0761(7) 0.2421(3) -0.2485(4) 0.0472(18) Uani 1 1 d . . . O13 O -0.2989(9) 0.3061(4) 0.2784(5) 0.066(2) Uani 1 1 d . . . N1 N -0.6331(8) 0.2151(4) -0.1185(5) 0.040(2) Uani 1 1 d . . . N2 N -0.7690(9) 0.5305(4) -0.1370(5) 0.043(2) Uani 1 1 d . . . N3 N -0.2128(9) 0.3211(4) -0.1848(5) 0.049(2) Uani 1 1 d . . . C1 C -0.3077(12) 0.3612(6) 0.2715(7) 0.051(3) Uani 1 1 d . . . C2 C -0.280(2) 0.3997(8) 0.3411(10) 0.139(7) Uani 1 1 d . . . H2A H -0.2913 0.4429 0.3264 0.208 Uiso 1 1 calc R . . H2B H -0.1836 0.3925 0.3858 0.208 Uiso 1 1 calc R . . H2C H -0.3461 0.3886 0.3564 0.208 Uiso 1 1 calc R . . C12 C -0.6684(12) 0.1612(6) -0.2325(7) 0.070(4) Uani 1 1 d . . . H12 H -0.6273 0.1418 -0.2576 0.084 Uiso 1 1 calc R . . C13 C -0.8113(12) 0.1618(5) -0.2691(7) 0.060(3) Uani 1 1 d . . . H13 H -0.8708 0.1431 -0.3191 0.072 Uiso 1 1 calc R . . C14 C -0.8673(10) 0.1923(4) -0.2279(6) 0.039(2) Uani 1 1 d . . . C15 C -0.7720(10) 0.2181(4) -0.1530(6) 0.043(3) Uani 1 1 d . . . H15 H -0.8084 0.2385 -0.1260 0.051 Uiso 1 1 calc R . . C16 C -1.0282(11) 0.1962(5) -0.2620(6) 0.042(3) Uani 1 1 d . . . C21 C -0.2969(11) 0.3341(5) -0.0242(6) 0.042(3) Uani 1 1 d . . . C22 C -0.2299(11) 0.3464(5) -0.0707(6) 0.044(3) Uani 1 1 d . . . C23 C -0.1109(13) 0.3849(6) -0.0434(8) 0.072(4) Uani 1 1 d . . . H23 H -0.0709 0.4050 0.0061 0.086 Uiso 1 1 calc R . . C24 C -0.0525(16) 0.3934(7) -0.0893(9) 0.092(5) Uani 1 1 d . . . H24 H 0.0202 0.4223 -0.0742 0.110 Uiso 1 1 calc R . . C25 C -0.1019(14) 0.3592(6) -0.1558(8) 0.074(4) Uani 1 1 d . . . H25 H -0.0556 0.3624 -0.1837 0.089 Uiso 1 1 calc R . . C26 C -0.2756(12) 0.3138(5) -0.1426(6) 0.049(3) Uani 1 1 d . . . H26 H -0.3520 0.2862 -0.1618 0.059 Uiso 1 1 calc R . . C31 C -0.6058(9) 0.3818(4) -0.0254(6) 0.036(2) Uani 1 1 d . . . C32 C -0.7052(10) 0.4258(4) -0.0924(6) 0.036(2) Uani 1 1 d . . . C33 C -0.7983(11) 0.4046(5) -0.1689(6) 0.051(3) Uani 1 1 d . . . H33 H -0.8066 0.3621 -0.1802 0.061 Uiso 1 1 calc R . . C34 C -0.8795(12) 0.4469(5) -0.2290(7) 0.059(3) Uani 1 1 d . . . H34 H -0.9473 0.4332 -0.2809 0.071 Uiso 1 1 calc R . . C35 C -0.8603(11) 0.5085(5) -0.2122(7) 0.054(3) Uani 1 1 d . . . H35 H -0.9119 0.5368 -0.2541 0.065 Uiso 1 1 calc R . . C36 C -0.6942(10) 0.4895(4) -0.0790(6) 0.039(2) Uani 1 1 d . . . H36 H -0.6312 0.5040 -0.0268 0.047 Uiso 1 1 calc R . . C37 C -0.5819(11) 0.1888(5) -0.1585(7) 0.054(3) Uani 1 1 d . . . H37 H -0.4833 0.1890 -0.1357 0.065 Uiso 1 1 calc R . . C41 C -0.6143(11) 0.2105(5) 0.1027(7) 0.045(3) Uani 1 1 d . . . C42 C -0.7526(12) 0.2028(5) 0.0978(7) 0.052(3) Uani 1 1 d . . . C43 C -0.8820(14) 0.2123(7) 0.0272(9) 0.083(4) Uani 1 1 d . . . C44 C -1.0129(15) 0.2077(8) 0.0276(12) 0.124(6) Uani 0.50 1 d P . . H44 H -1.1030 0.2157 -0.0179 0.149 Uiso 0.50 1 calc PR . . N44 N -1.0129(15) 0.2077(8) 0.0276(12) 0.124(6) Uani 0.50 1 d P . . C45 C -0.993(2) 0.1907(8) 0.0996(16) 0.114(7) Uani 1 1 d . . . C46 C -0.8686(17) 0.1798(6) 0.1686(9) 0.085(4) Uani 0.50 1 d P . . H46 H -0.8633 0.1677 0.2156 0.103 Uiso 0.50 1 calc PR . . N46 N -0.8686(17) 0.1798(6) 0.1686(9) 0.085(4) Uani 0.50 1 d P . . C47 C -0.7517(15) 0.1877(6) 0.1655(9) 0.078(4) Uani 1 1 d . . . C51 C -0.3250(10) 0.1337(5) 0.0843(7) 0.043(3) Uani 1 1 d . . . C52 C -0.3062(11) 0.0656(5) 0.0713(8) 0.055(3) Uani 1 1 d . . . C53 C -0.3610(17) 0.0441(6) -0.0044(9) 0.088(5) Uani 1 1 d . . . C54 C -0.3518(16) -0.0156(6) -0.0239(9) 0.102(5) Uani 0.50 1 d P . . H54 H -0.3892 -0.0291 -0.0767 0.122 Uiso 0.50 1 calc PR . . N54 N -0.3518(16) -0.0156(6) -0.0239(9) 0.102(5) Uani 0.50 1 d P . . C55 C -0.2824(19) -0.0538(7) 0.0415(14) 0.107(6) Uani 1 1 d . . . C56 C -0.2308(18) -0.0364(7) 0.1206(10) 0.116(6) Uani 0.50 1 d P . . H56 H -0.1887 -0.0651 0.1627 0.140 Uiso 0.50 1 calc PR . . N56 N -0.2308(18) -0.0364(7) 0.1206(10) 0.116(6) Uani 0.50 1 d P . . C57 C -0.2446(14) 0.0237(6) 0.1337(8) 0.070(4) Uani 1 1 d . . . H43 H -0.8864 0.2240 -0.0197 0.085 Uiso 1 1 d . . . H45 H -1.0674 0.1884 0.1028 0.085 Uiso 1 1 d . . . H47 H -0.6656 0.1810 0.2160 0.085 Uiso 1 1 d . . . H53 H -0.4006 0.0722 -0.0485 0.085 Uiso 1 1 d . . . H55 H -0.2734 -0.0940 0.0328 0.085 Uiso 1 1 d . . . H57 H -0.2074 0.0346 0.1854 0.085 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe1 0.0310(7) 0.0401(9) 0.0390(9) -0.0004(6) 0.0170(6) -0.0001(6) Fe2 0.0358(8) 0.0395(9) 0.0371(9) 0.0008(6) 0.0160(6) 0.0038(6) Fe3 0.0358(8) 0.0503(10) 0.0375(9) 0.0023(7) 0.0193(7) 0.0011(7) O1 0.037(4) 0.041(4) 0.052(5) -0.008(3) 0.023(3) -0.008(3) O2 0.044(4) 0.026(4) 0.059(5) -0.001(3) 0.007(4) 0.000(3) O3 0.052(4) 0.062(5) 0.038(4) -0.019(3) 0.027(4) -0.025(4) O4 0.054(5) 0.045(5) 0.047(5) 0.007(3) 0.025(4) 0.017(4) O5 0.044(4) 0.064(5) 0.051(5) -0.006(4) 0.027(4) -0.016(4) O6 0.040(4) 0.050(5) 0.039(4) -0.002(3) 0.015(3) 0.003(3) O7 0.083(6) 0.048(5) 0.050(5) -0.012(4) 0.047(5) -0.012(4) O8 0.029(4) 0.043(5) 0.081(6) -0.014(4) 0.016(4) -0.005(3) O9 0.082(6) 0.048(5) 0.059(6) -0.002(4) 0.044(5) 0.010(4) O10 0.041(4) 0.092(6) 0.043(5) 0.010(4) 0.023(4) 0.001(4) O11 0.069(5) 0.048(5) 0.054(5) 0.006(4) 0.032(4) 0.004(4) O12 0.041(4) 0.048(5) 0.048(5) -0.014(3) 0.021(4) -0.001(3) O13 0.091(6) 0.039(5) 0.059(6) 0.006(4) 0.035(5) 0.010(4) N1 0.024(4) 0.050(5) 0.043(5) -0.012(4) 0.016(4) -0.002(4) N2 0.043(5) 0.042(5) 0.038(5) -0.001(4) 0.019(4) 0.005(4) N3 0.041(5) 0.065(6) 0.044(6) -0.004(4) 0.025(5) -0.008(4) C1 0.060(7) 0.054(8) 0.045(7) 0.002(6) 0.031(6) 0.002(6) C2 0.22(2) 0.155(17) 0.087(14) -0.015(12) 0.108(15) -0.012(16) C12 0.045(7) 0.123(11) 0.052(8) -0.020(7) 0.031(6) 0.004(7) C13 0.042(7) 0.076(9) 0.058(8) -0.025(6) 0.024(6) 0.000(6) C14 0.032(5) 0.035(6) 0.045(6) -0.011(4) 0.018(5) -0.009(4) C15 0.037(6) 0.039(6) 0.046(7) -0.008(5) 0.018(5) 0.000(5) C16 0.045(6) 0.039(7) 0.034(6) 0.003(5) 0.015(5) -0.003(5) C21 0.044(6) 0.053(7) 0.032(6) 0.004(5) 0.023(5) 0.009(5) C22 0.057(7) 0.049(7) 0.032(6) -0.007(5) 0.027(5) -0.010(5) C23 0.074(9) 0.086(10) 0.076(9) -0.040(7) 0.055(8) -0.045(7) C24 0.113(12) 0.112(12) 0.088(11) -0.061(9) 0.078(10) -0.076(10) C25 0.071(9) 0.095(10) 0.081(10) -0.033(8) 0.056(8) -0.034(8) C26 0.056(7) 0.055(7) 0.045(7) 0.003(5) 0.033(6) 0.004(5) C31 0.025(5) 0.030(6) 0.045(6) 0.008(4) 0.013(4) 0.004(4) C32 0.034(5) 0.031(6) 0.041(6) 0.002(4) 0.019(5) 0.002(4) C33 0.048(7) 0.036(7) 0.043(7) -0.004(5) 0.008(5) 0.002(5) C34 0.054(7) 0.056(8) 0.036(7) 0.005(5) 0.003(5) -0.002(6) C35 0.049(7) 0.036(7) 0.045(7) 0.005(5) 0.003(5) -0.003(5) C36 0.037(6) 0.040(7) 0.045(6) 0.015(5) 0.025(5) 0.011(4) C37 0.031(6) 0.069(8) 0.049(7) -0.009(6) 0.013(5) 0.000(5) C41 0.040(6) 0.048(7) 0.045(7) -0.001(5) 0.021(6) -0.003(5) C42 0.047(7) 0.055(7) 0.061(8) 0.010(6) 0.034(6) 0.006(5) C43 0.054(8) 0.101(11) 0.092(11) 0.043(9) 0.038(8) 0.018(8) C44 0.059(9) 0.151(15) 0.165(18) 0.036(13) 0.062(11) 0.009(9) N44 0.059(9) 0.151(15) 0.165(18) 0.036(13) 0.062(11) 0.009(9) C45 0.087(13) 0.122(15) 0.19(2) 0.021(15) 0.109(16) 0.001(11) C46 0.089(11) 0.092(10) 0.106(12) 0.005(8) 0.072(10) -0.007(8) N46 0.089(11) 0.092(10) 0.106(12) 0.005(8) 0.072(10) -0.007(8) C47 0.070(9) 0.088(10) 0.083(11) 0.006(8) 0.046(9) -0.005(7) C51 0.036(6) 0.043(7) 0.045(7) 0.003(5) 0.019(5) -0.001(5) C52 0.043(6) 0.044(8) 0.059(8) 0.008(6) 0.015(6) 0.005(5) C53 0.121(13) 0.048(9) 0.085(12) 0.003(7) 0.049(10) 0.011(8) C54 0.138(13) 0.045(9) 0.096(12) -0.005(7) 0.044(10) 0.001(8) N54 0.138(13) 0.045(9) 0.096(12) -0.005(7) 0.044(10) 0.001(8) C55 0.109(14) 0.049(10) 0.16(2) -0.005(11) 0.073(15) 0.006(9) C56 0.153(15) 0.068(11) 0.104(14) 0.018(9) 0.053(12) 0.026(10) N56 0.153(15) 0.068(11) 0.104(14) 0.018(9) 0.053(12) 0.026(10) C57 0.095(10) 0.043(8) 0.061(9) 0.010(6) 0.034(8) 0.013(7) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 Fe1 O1 1.888(7) . ? Fe1 O4 2.021(7) . ? Fe1 O2 2.044(7) . ? Fe1 O5 2.060(7) . ? Fe1 O3 2.075(7) . ? Fe1 N1 2.232(8) . ? Fe2 O1 1.844(6) . ? Fe2 O8 2.010(7) 4_666 ? Fe2 O9 2.023(8) . ? Fe2 O7 2.024(7) . ? Fe2 O6 2.049(7) . ? Fe2 N2 2.256(8) 3_465 ? Fe3 O1 1.978(7) . ? Fe3 O10 2.095(7) . ? Fe3 O13 2.110(8) . ? Fe3 O12 2.113(7) 4_666 ? Fe3 O11 2.120(8) . ? Fe3 N3 2.186(9) 4_566 ? O2 C31 1.231(10) . ? O3 C21 1.258(12) . ? O4 C51 1.263(11) . ? O5 C41 1.273(12) . ? O6 C31 1.284(11) . ? O7 C21 1.245(11) . ? O8 C16 1.285(11) . ? O8 Fe2 2.010(7) 4_465 ? O9 C1 1.255(13) . ? O10 C41 1.229(12) . ? O11 C51 1.260(12) . ? O12 C16 1.214(11) . ? O12 Fe3 2.113(7) 4_465 ? O13 C1 1.188(12) . ? N1 C15 1.306(11) . ? N1 C37 1.316(13) . ? N2 C36 1.320(11) . ? N2 C35 1.349(12) . ? N2 Fe2 2.256(8) 3_465 ? N3 C25 1.324(13) . ? N3 C26 1.345(12) . ? N3 Fe3 2.186(9) 4_565 ? C1 C2 1.480(18) . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C12 H12 0.9300 . ? C13 C14 1.416(14) . ? C13 H13 0.9300 . ? C14 C16 1.532(13) . ? C15 H15 0.9300 . ? C21 C22 1.476(14) . ? C22 C26 1.402(14) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? C31 C32 1.509(12) . ? C33 H33 0.9300 . ? C34 H34 0.9300 . ? C35 H35 0.9300 . ? C36 H36 0.9300 . ? C37 H37 0.9300 . ? C41 C42 1.489(14) . ? C43 C44 1.456(18) . ? C43 H43 0.929 . ? C44 H44 0.9300 . ? C45 H45 0.857 . ? C46 H46 0.9300 . ? C47 H47 0.947 . ? C51 C52 1.518(14) . ? C53 H53 0.946 . ? C54 C55 1.36(2) . ? C54 H54 0.9300 . ? C55 H55 0.895 . ? C56 H56 0.9300 . ? C57 H57 0.896 . ? 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 O1 Fe1 O4 100.3(3) . . ? O1 Fe1 O2 96.1(3) . . ? O4 Fe1 O2 163.5(3) . . ? O1 Fe1 O5 95.4(3) . . ? O4 Fe1 O5 92.4(3) . . ? O2 Fe1 O5 87.5(3) . . ? O1 Fe1 O3 93.7(3) . . ? O4 Fe1 O3 88.9(3) . . ? O2 Fe1 O3 88.6(3) . . ? O5 Fe1 O3 170.4(3) . . ? O1 Fe1 N1 175.8(3) . . ? O4 Fe1 N1 82.8(3) . . ? O2 Fe1 N1 80.7(3) . . ? O5 Fe1 N1 87.2(3) . . ? O3 Fe1 N1 83.5(3) . . ? O1 Fe2 O8 94.9(3) . 4_666 ? O1 Fe2 O9 99.3(3) . . ? O8 Fe2 O9 92.9(3) 4_666 . ? O1 Fe2 O7 97.1(3) . . ? O8 Fe2 O7 88.4(3) 4_666 . ? O9 Fe2 O7 163.4(3) . . ? O1 Fe2 O6 96.8(3) . . ? O8 Fe2 O6 167.7(3) 4_666 . ? O9 Fe2 O6 88.8(3) . . ? O7 Fe2 O6 86.6(3) . . ? O1 Fe2 N2 178.1(3) . 3_465 ? O8 Fe2 N2 83.2(3) 4_666 3_465 ? O9 Fe2 N2 81.4(3) . 3_465 ? O7 Fe2 N2 82.3(3) . 3_465 ? O6 Fe2 N2 85.0(3) . 3_465 ? O1 Fe3 O10 91.5(3) . . ? O1 Fe3 O13 95.8(3) . . ? O10 Fe3 O13 88.9(3) . . ? O1 Fe3 O12 92.3(3) . 4_666 ? O10 Fe3 O12 176.0(3) . 4_666 ? O13 Fe3 O12 89.4(3) . 4_666 ? O1 Fe3 O11 97.1(3) . . ? O10 Fe3 O11 89.9(3) . . ? O13 Fe3 O11 167.1(3) . . ? O12 Fe3 O11 91.1(3) 4_666 . ? O1 Fe3 N3 178.7(3) . 4_566 ? O10 Fe3 N3 89.3(3) . 4_566 ? O13 Fe3 N3 83.2(3) . 4_566 ? O12 Fe3 N3 86.9(3) 4_666 4_566 ? O11 Fe3 N3 83.9(3) . 4_566 ? Fe2 O1 Fe1 122.1(4) . . ? Fe2 O1 Fe3 119.5(3) . . ? Fe1 O1 Fe3 118.3(3) . . ? C31 O2 Fe1 132.9(6) . . ? C21 O3 Fe1 130.2(6) . . ? C51 O4 Fe1 129.6(7) . . ? C41 O5 Fe1 129.7(7) . . ? C31 O6 Fe2 127.7(6) . . ? C21 O7 Fe2 132.0(7) . . ? C16 O8 Fe2 132.2(7) . 4_465 ? C1 O9 Fe2 128.2(8) . . ? C41 O10 Fe3 131.7(7) . . ? C51 O11 Fe3 131.8(7) . . ? C16 O12 Fe3 128.7(7) . 4_465 ? C1 O13 Fe3 132.2(8) . . ? C15 N1 C37 118.4(9) . . ? C15 N1 Fe1 120.9(7) . . ? C37 N1 Fe1 120.6(6) . . ? C36 N2 C35 117.6(9) . . ? C36 N2 Fe2 119.9(7) . 3_465 ? C35 N2 Fe2 119.2(7) . 3_465 ? C25 N3 C26 118.3(10) . . ? C25 N3 Fe3 123.6(8) . 4_565 ? C26 N3 Fe3 118.0(7) . 4_565 ? O13 C1 O9 128.6(11) . . ? O13 C1 C2 119.1(12) . . ? O9 C1 C2 112.2(12) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C13 C12 C37 121.0(11) . . ? C13 C12 H12 119.5 . . ? C37 C12 H12 119.5 . . ? C12 C13 C14 116.8(10) . . ? C12 C13 H13 121.6 . . ? C14 C13 H13 121.6 . . ? C15 C14 C13 118.3(9) . . ? C15 C14 C16 119.1(9) . . ? C13 C14 C16 122.6(9) . . ? N1 C15 C14 123.0(10) . . ? N1 C15 H15 118.5 . . ? C14 C15 H15 118.5 . . ? O12 C16 O8 128.3(10) . . ? O12 C16 C14 119.3(9) . . ? O8 C16 C14 112.4(9) . . ? O7 C21 O3 125.9(10) . . ? O7 C21 C22 116.7(10) . . ? O3 C21 C22 117.3(9) . . ? C23 C22 C26 116.0(10) . . ? C23 C22 C21 123.5(10) . . ? C26 C22 C21 120.1(9) . . ? C24 C23 C22 120.4(11) . . ? C24 C23 H23 119.8 . . ? C22 C23 H23 119.8 . . ? C25 C24 C23 118.7(12) . . ? C25 C24 H24 120.7 . . ? C23 C24 H24 120.7 . . ? N3 C25 C24 124.0(12) . . ? N3 C25 H25 118.0 . . ? C24 C25 H25 118.0 . . ? N3 C26 C22 122.2(10) . . ? N3 C26 H26 118.9 . . ? C22 C26 H26 118.9 . . ? O2 C31 O6 125.7(8) . . ? O2 C31 C32 116.5(9) . . ? O6 C31 C32 117.5(8) . . ? C33 C32 C36 118.4(9) . . ? C33 C32 C31 121.0(9) . . ? C36 C32 C31 120.3(9) . . ? C32 C33 C34 118.9(10) . . ? C32 C33 H33 120.6 . . ? C34 C33 H33 120.6 . . ? C35 C34 C33 119.6(10) . . ? C35 C34 H34 120.2 . . ? C33 C34 H34 120.2 . . ? N2 C35 C34 122.4(10) . . ? N2 C35 H35 118.8 . . ? C34 C35 H35 118.8 . . ? N2 C36 C32 123.0(10) . . ? N2 C36 H36 118.5 . . ? C32 C36 H36 118.5 . . ? N1 C37 C12 122.4(10) . . ? N1 C37 H37 118.8 . . ? C12 C37 H37 118.8 . . ? O10 C41 O5 126.6(10) . . ? O10 C41 C42 118.9(10) . . ? O5 C41 C42 114.5(9) . . ? C47 C42 C43 118.5(11) . . ? C47 C42 C41 119.6(11) . . ? C43 C42 C41 121.9(11) . . ? C42 C43 C44 119.1(14) . . ? C42 C43 H43 120.7(13) . . ? C44 C43 H43 120.1(14) . . ? C45 C44 C43 114.8(15) . . ? C45 C44 H44 122.6 . . ? C43 C44 H44 122.6 . . ? C46 C45 C44 126.9(14) . . ? C46 C45 H45 115(2) . . ? C44 C45 H45 118(2) . . ? C45 C46 C47 115.5(14) . . ? C45 C46 H46 122.2 . . ? C47 C46 H46 122.2 . . ? C46 C47 C42 125.0(14) . . ? C46 C47 H47 112.8(15) . . ? C42 C47 H47 122.3(14) . . ? O11 C51 O4 126.4(10) . . ? O11 C51 C52 116.6(9) . . ? O4 C51 C52 117.1(10) . . ? C53 C52 C57 118.3(12) . . ? C53 C52 C51 119.5(11) . . ? C57 C52 C51 122.0(12) . . ? C52 C53 C54 125.1(13) . . ? C52 C53 H53 120.2(13) . . ? C54 C53 H53 114.3(15) . . ? C53 C54 C55 113.1(15) . . ? C53 C54 H54 123.4 . . ? C55 C54 H54 123.4 . . ? C54 C55 C56 125.4(15) . . ? C54 C55 H55 118(2) . . ? C56 C55 H55 117(2) . . ? C57 C56 C55 116.9(14) . . ? C57 C56 H56 121.5 . . ? C55 C56 H56 121.5 . . ? C56 C57 C52 120.9(14) . . ? C56 C57 H57 116.0(14) . . ? C52 C57 H57 123.0(13) . . ? 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 O8 Fe2 O1 Fe1 -130.8(4) 4_666 . . . ? O9 Fe2 O1 Fe1 135.4(4) . . . . ? O7 Fe2 O1 Fe1 -41.9(4) . . . . ? O6 Fe2 O1 Fe1 45.6(4) . . . . ? N2 Fe2 O1 Fe1 -114(9) 3_465 . . . ? O8 Fe2 O1 Fe3 50.2(4) 4_666 . . . ? O9 Fe2 O1 Fe3 -43.5(4) . . . . ? O7 Fe2 O1 Fe3 139.2(4) . . . . ? O6 Fe2 O1 Fe3 -133.4(4) . . . . ? N2 Fe2 O1 Fe3 67(9) 3_465 . . . ? O4 Fe1 O1 Fe2 138.1(4) . . . . ? O2 Fe1 O1 Fe2 -40.4(4) . . . . ? O5 Fe1 O1 Fe2 -128.5(4) . . . . ? O3 Fe1 O1 Fe2 48.5(4) . . . . ? N1 Fe1 O1 Fe2 0(4) . . . . ? O4 Fe1 O1 Fe3 -42.9(4) . . . . ? O2 Fe1 O1 Fe3 138.5(4) . . . . ? O5 Fe1 O1 Fe3 50.5(4) . . . . ? O3 Fe1 O1 Fe3 -132.5(4) . . . . ? N1 Fe1 O1 Fe3 179(100) . . . . ? O10 Fe3 O1 Fe2 125.2(4) . . . . ? O13 Fe3 O1 Fe2 36.2(4) . . . . ? O12 Fe3 O1 Fe2 -53.4(4) 4_666 . . . ? O11 Fe3 O1 Fe2 -144.7(4) . . . . ? N3 Fe3 O1 Fe2 -2(14) 4_566 . . . ? O10 Fe3 O1 Fe1 -53.8(4) . . . . ? O13 Fe3 O1 Fe1 -142.8(4) . . . . ? O12 Fe3 O1 Fe1 127.6(4) 4_666 . . . ? O11 Fe3 O1 Fe1 36.3(4) . . . . ? N3 Fe3 O1 Fe1 179(100) 4_566 . . . ? O1 Fe1 O2 C31 22.0(10) . . . . ? O4 Fe1 O2 C31 -153.1(10) . . . . ? O5 Fe1 O2 C31 117.1(10) . . . . ? O3 Fe1 O2 C31 -71.6(9) . . . . ? N1 Fe1 O2 C31 -155.3(10) . . . . ? O1 Fe1 O3 C21 -29.1(9) . . . . ? O4 Fe1 O3 C21 -129.4(9) . . . . ? O2 Fe1 O3 C21 66.9(9) . . . . ? O5 Fe1 O3 C21 132.6(16) . . . . ? N1 Fe1 O3 C21 147.7(9) . . . . ? O1 Fe1 O4 C51 36.2(9) . . . . ? O2 Fe1 O4 C51 -148.8(10) . . . . ? O5 Fe1 O4 C51 -59.7(9) . . . . ? O3 Fe1 O4 C51 129.8(9) . . . . ? N1 Fe1 O4 C51 -146.6(9) . . . . ? O1 Fe1 O5 C41 -10.8(9) . . . . ? O4 Fe1 O5 C41 89.8(9) . . . . ? O2 Fe1 O5 C41 -106.7(9) . . . . ? O3 Fe1 O5 C41 -172.6(15) . . . . ? N1 Fe1 O5 C41 172.4(9) . . . . ? O1 Fe2 O6 C31 -36.2(8) . . . . ? O8 Fe2 O6 C31 126.7(15) 4_666 . . . ? O9 Fe2 O6 C31 -135.4(8) . . . . ? O7 Fe2 O6 C31 60.6(8) . . . . ? N2 Fe2 O6 C31 143.1(8) 3_465 . . . ? O1 Fe2 O7 C21 6.5(10) . . . . ? O8 Fe2 O7 C21 101.2(9) 4_666 . . . ? O9 Fe2 O7 C21 -164.2(10) . . . . ? O6 Fe2 O7 C21 -90.0(9) . . . . ? N2 Fe2 O7 C21 -175.4(10) 3_465 . . . ? O1 Fe2 O9 C1 35.9(10) . . . . ? O8 Fe2 O9 C1 -59.5(10) 4_666 . . . ? O7 Fe2 O9 C1 -153.5(11) . . . . ? O6 Fe2 O9 C1 132.6(10) . . . . ? N2 Fe2 O9 C1 -142.2(10) 3_465 . . . ? O1 Fe3 O10 C41 22.3(10) . . . . ? O13 Fe3 O10 C41 118.0(10) . . . . ? O12 Fe3 O10 C41 -178(97) 4_666 . . . ? O11 Fe3 O10 C41 -74.8(10) . . . . ? N3 Fe3 O10 C41 -158.8(10) 4_566 . . . ? O1 Fe3 O11 C51 -18.3(10) . . . . ? O10 Fe3 O11 C51 73.3(10) . . . . ? O13 Fe3 O11 C51 157.5(13) . . . . ? O12 Fe3 O11 C51 -110.7(10) 4_666 . . . ? N3 Fe3 O11 C51 162.5(10) 4_566 . . . ? O1 Fe3 O13 C1 -15.5(11) . . . . ? O10 Fe3 O13 C1 -107.0(11) . . . . ? O12 Fe3 O13 C1 76.7(11) 4_666 . . . ? O11 Fe3 O13 C1 168.7(12) . . . . ? N3 Fe3 O13 C1 163.7(11) 4_566 . . . ? O1 Fe1 N1 C15 -90(4) . . . . ? O4 Fe1 N1 C15 131.8(8) . . . . ? O2 Fe1 N1 C15 -48.8(8) . . . . ? O5 Fe1 N1 C15 39.0(8) . . . . ? O3 Fe1 N1 C15 -138.5(8) . . . . ? O1 Fe1 N1 C37 92(4) . . . . ? O4 Fe1 N1 C37 -46.5(8) . . . . ? O2 Fe1 N1 C37 132.8(9) . . . . ? O5 Fe1 N1 C37 -139.3(8) . . . . ? O3 Fe1 N1 C37 43.2(8) . . . . ? Fe3 O13 C1 O9 8(2) . . . . ? Fe3 O13 C1 C2 -167.4(11) . . . . ? Fe2 O9 C1 O13 -19.5(19) . . . . ? Fe2 O9 C1 C2 156.4(10) . . . . ? C37 C12 C13 C14 0(2) . . . . ? C12 C13 C14 C15 -1.2(17) . . . . ? C12 C13 C14 C16 -179.4(11) . . . . ? C37 N1 C15 C14 3.2(16) . . . . ? Fe1 N1 C15 C14 -175.1(8) . . . . ? C13 C14 C15 N1 -0.6(16) . . . . ? C16 C14 C15 N1 177.7(9) . . . . ? Fe3 O12 C16 O8 -4.3(17) 4_465 . . . ? Fe3 O12 C16 C14 174.6(6) 4_465 . . . ? Fe2 O8 C16 O12 11.2(17) 4_465 . . . ? Fe2 O8 C16 C14 -167.7(7) 4_465 . . . ? C15 C14 C16 O12 35.2(14) . . . . ? C13 C14 C16 O12 -146.5(11) . . . . ? C15 C14 C16 O8 -145.7(10) . . . . ? C13 C14 C16 O8 32.5(14) . . . . ? Fe2 O7 C21 O3 13.2(16) . . . . ? Fe2 O7 C21 C22 -166.5(7) . . . . ? Fe1 O3 C21 O7 1.1(16) . . . . ? Fe1 O3 C21 C22 -179.1(7) . . . . ? O7 C21 C22 C23 21.3(16) . . . . ? O3 C21 C22 C23 -158.5(11) . . . . ? O7 C21 C22 C26 -165.5(9) . . . . ? O3 C21 C22 C26 14.7(15) . . . . ? C26 C22 C23 C24 5.3(19) . . . . ? C21 C22 C23 C24 178.8(13) . . . . ? C22 C23 C24 C25 -7(2) . . . . ? C26 N3 C25 C24 -3(2) . . . . ? Fe3 N3 C25 C24 -179.7(12) 4_565 . . . ? C23 C24 C25 N3 6(3) . . . . ? C25 N3 C26 C22 1.7(16) . . . . ? Fe3 N3 C26 C22 178.3(8) 4_565 . . . ? C23 C22 C26 N3 -2.7(16) . . . . ? C21 C22 C26 N3 -176.5(9) . . . . ? Fe1 O2 C31 O6 -16.0(16) . . . . ? Fe1 O2 C31 C32 156.9(7) . . . . ? Fe2 O6 C31 O2 23.9(15) . . . . ? Fe2 O6 C31 C32 -149.0(7) . . . . ? O2 C31 C32 C33 -4.9(14) . . . . ? O6 C31 C32 C33 168.6(10) . . . . ? O2 C31 C32 C36 -178.7(9) . . . . ? O6 C31 C32 C36 -5.2(14) . . . . ? C36 C32 C33 C34 -1.6(16) . . . . ? C31 C32 C33 C34 -175.5(10) . . . . ? C32 C33 C34 C35 3.5(18) . . . . ? C36 N2 C35 C34 1.8(17) . . . . ? Fe2 N2 C35 C34 161.4(9) 3_465 . . . ? C33 C34 C35 N2 -3.7(19) . . . . ? C35 N2 C36 C32 0.3(14) . . . . ? Fe2 N2 C36 C32 -159.2(7) 3_465 . . . ? C33 C32 C36 N2 -0.3(14) . . . . ? C31 C32 C36 N2 173.6(9) . . . . ? C15 N1 C37 C12 -4.2(17) . . . . ? Fe1 N1 C37 C12 174.2(10) . . . . ? C13 C12 C37 N1 2(2) . . . . ? Fe3 O10 C41 O5 14.0(17) . . . . ? Fe3 O10 C41 C42 -167.7(7) . . . . ? Fe1 O5 C41 O10 -21.9(17) . . . . ? Fe1 O5 C41 C42 159.7(7) . . . . ? O10 C41 C42 C47 -8.9(16) . . . . ? O5 C41 C42 C47 169.7(11) . . . . ? O10 C41 C42 C43 169.2(12) . . . . ? O5 C41 C42 C43 -12.2(16) . . . . ? C47 C42 C43 C44 2(2) . . . . ? C41 C42 C43 C44 -176.3(12) . . . . ? C42 C43 C44 C45 -3(2) . . . . ? C43 C44 C45 C46 2(3) . . . . ? C44 C45 C46 C47 1(3) . . . . ? C45 C46 C47 C42 -3(2) . . . . ? C43 C42 C47 C46 1(2) . . . . ? C41 C42 C47 C46 179.7(12) . . . . ? Fe3 O11 C51 O4 11.1(17) . . . . ? Fe3 O11 C51 C52 -170.4(7) . . . . ? Fe1 O4 C51 O11 -21.1(16) . . . . ? Fe1 O4 C51 C52 160.4(7) . . . . ? O11 C51 C52 C53 179.4(12) . . . . ? O4 C51 C52 C53 -1.9(17) . . . . ? O11 C51 C52 C57 4.5(16) . . . . ? O4 C51 C52 C57 -176.8(11) . . . . ? C57 C52 C53 C54 -5(2) . . . . ? C51 C52 C53 C54 -179.7(13) . . . . ? C52 C53 C54 C55 1(2) . . . . ? C53 C54 C55 C56 3(3) . . . . ? C54 C55 C56 C57 -4(3) . . . . ? C55 C56 C57 C52 0(2) . . . . ? C53 C52 C57 C56 4(2) . . . . ? C51 C52 C57 C56 179.1(13) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.415 _refine_diff_density_min -0.923 _refine_diff_density_rms 0.176