# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Vincent Artero' _publ_contact_author_email VARTERO@CEA.FR _publ_section_title ; A structural and functional mimic of the active site of NiFe hydrogenases ; loop_ _publ_author_name 'Vincent Artero' 'Sigolene Canaguier' 'Martin Field' 'Marc Fontecave' 'Y. Oudart' 'J Pecaut' # Attachment 'struc.cif' data_struc _database_code_depnum_ccdc_archive 'CCDC 760104' #TrackingRef 'struc.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H31 B Cl2 F4 Fe Ni O S4' _chemical_formula_weight 723.99 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source B B 0.0013 0.0007 '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' H H 0.0000 0.0000 '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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 10.161(2) _cell_length_b 22.746(5) _cell_length_c 13.340(3) _cell_angle_alpha 90.00 _cell_angle_beta 105.252(4) _cell_angle_gamma 90.00 _cell_volume 2974.5(12) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour dark_brown _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.617 _exptl_crystal_density_method ? _exptl_crystal_F_000 1480 _exptl_absorpt_coefficient_mu 1.624 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5628 _exptl_absorpt_correction_T_max 0.8545 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18506 _diffrn_reflns_av_R_equivalents 0.0274 _diffrn_reflns_av_sigmaI/netI 0.0350 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 28.34 _reflns_number_total 7024 _reflns_number_gt 5640 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0326P)^2^+2.8100P] 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_number_reflns 7024 _refine_ls_number_parameters 475 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0544 _refine_ls_R_factor_gt 0.0406 _refine_ls_wR_factor_ref 0.0901 _refine_ls_wR_factor_gt 0.0860 _refine_ls_goodness_of_fit_ref 1.104 _refine_ls_restrained_S_all 1.104 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni Ni 0.26636(3) 0.675907(15) 0.71378(3) 0.02469(9) Uani 1 1 d . . . Fe Fe 0.40512(4) 0.789720(17) 0.77643(3) 0.02497(10) Uani 1 1 d . . . S1 S 0.17952(7) 0.76196(3) 0.72446(5) 0.02913(15) Uani 1 1 d . . . S2 S 0.13816(6) 0.66484(3) 0.55584(5) 0.02617(14) Uani 1 1 d . . . S3 S 0.39292(7) 0.59882(3) 0.71110(5) 0.02786(15) Uani 1 1 d . . . S4 S 0.39751(7) 0.70342(3) 0.86259(5) 0.02887(15) Uani 1 1 d . . . O1 O 0.5144(3) 0.74236(13) 0.61283(19) 0.0597(7) Uani 1 1 d . . . C1 C 0.0894(3) 0.77556(13) 0.5885(2) 0.0322(6) Uani 1 1 d . . . H1A H 0.038(3) 0.8068(14) 0.588(2) 0.029(8) Uiso 1 1 d . . . H1B H 0.155(3) 0.7833(13) 0.546(2) 0.032(8) Uiso 1 1 d . . . C2 C 0.0035(3) 0.72188(12) 0.5423(2) 0.0307(6) Uani 1 1 d . . . C3 C -0.0629(4) 0.73074(17) 0.4268(3) 0.0430(8) Uani 1 1 d . . . H3A H 0.002(4) 0.7416(16) 0.388(3) 0.047(10) Uiso 1 1 d . . . H3B H -0.107(4) 0.6955(16) 0.395(3) 0.046(10) Uiso 1 1 d . . . H3C H -0.127(4) 0.7617(18) 0.422(3) 0.059(11) Uiso 1 1 d . . . C4 C -0.1019(3) 0.70606(16) 0.6002(3) 0.0400(7) Uani 1 1 d . . . H4A H -0.065(3) 0.6977(13) 0.671(2) 0.030(8) Uiso 1 1 d . . . H4B H -0.154(3) 0.6708(15) 0.570(3) 0.044(9) Uiso 1 1 d . . . H4C H -0.159(4) 0.7403(16) 0.594(3) 0.049(10) Uiso 1 1 d . . . C5 C 0.0502(3) 0.59373(13) 0.5397(3) 0.0319(6) Uani 1 1 d . . . H5A H 0.034(3) 0.5823(13) 0.603(2) 0.030(8) Uiso 1 1 d . . . H5B H -0.027(3) 0.6000(14) 0.490(3) 0.038(9) Uiso 1 1 d . . . C6 C 0.1368(3) 0.54881(12) 0.5037(2) 0.0291(6) Uani 1 1 d . . . C7 C 0.1070(3) 0.53591(13) 0.3978(2) 0.0358(7) Uani 1 1 d . . . H7 H 0.036(3) 0.5559(14) 0.353(3) 0.039(9) Uiso 1 1 d . . . C8 C 0.1843(4) 0.49601(15) 0.3601(3) 0.0410(7) Uani 1 1 d . . . H8 H 0.165(3) 0.4895(15) 0.295(3) 0.042(9) Uiso 1 1 d . . . C9 C 0.2931(4) 0.46795(15) 0.4273(3) 0.0428(8) Uani 1 1 d . . . H9 H 0.343(3) 0.4433(15) 0.405(3) 0.042(9) Uiso 1 1 d . . . C10 C 0.3233(3) 0.48026(14) 0.5321(3) 0.0387(7) Uani 1 1 d . . . H10 H 0.393(3) 0.4641(16) 0.575(3) 0.047(10) Uiso 1 1 d . . . C11 C 0.2467(3) 0.52026(12) 0.5723(2) 0.0304(6) Uani 1 1 d . . . C12 C 0.2874(3) 0.53230(13) 0.6868(2) 0.0336(6) Uani 1 1 d . . . H12A H 0.215(3) 0.5366(13) 0.716(2) 0.032(8) Uiso 1 1 d . . . H12B H 0.339(3) 0.5020(15) 0.723(2) 0.042(9) Uiso 1 1 d . . . C13 C 0.4988(3) 0.59201(13) 0.8478(2) 0.0336(6) Uani 1 1 d . . . C14 C 0.4168(4) 0.56867(16) 0.9192(3) 0.0415(8) Uani 1 1 d . . . H14A H 0.392(3) 0.5298(15) 0.908(2) 0.036(9) Uiso 1 1 d . . . H14B H 0.337(4) 0.5908(16) 0.918(3) 0.045(10) Uiso 1 1 d . . . H14C H 0.473(4) 0.5717(16) 0.988(3) 0.053(10) Uiso 1 1 d . . . C15 C 0.6204(4) 0.55259(17) 0.8479(3) 0.0483(9) Uani 1 1 d . . . H15A H 0.677(4) 0.5710(17) 0.805(3) 0.055(11) Uiso 1 1 d . . . H15B H 0.588(4) 0.5122(18) 0.821(3) 0.061(11) Uiso 1 1 d . . . H15C H 0.671(4) 0.5470(15) 0.913(3) 0.047(10) Uiso 1 1 d . . . C16 C 0.5454(3) 0.65545(13) 0.8737(3) 0.0344(7) Uani 1 1 d . . . H16A H 0.597(3) 0.6570(12) 0.944(2) 0.024(7) Uiso 1 1 d . . . H16B H 0.598(3) 0.6693(15) 0.827(3) 0.047(10) Uiso 1 1 d . . . C21 C 0.4522(3) 0.87609(13) 0.7482(3) 0.0374(7) Uani 1 1 d . . . H21 H 0.444(3) 0.8918(14) 0.684(3) 0.038(9) Uiso 1 1 d . . . C22 C 0.3508(3) 0.87616(13) 0.8022(3) 0.0398(7) Uani 1 1 d . . . H22 H 0.260(4) 0.8900(15) 0.772(3) 0.047(10) Uiso 1 1 d . . . C23 C 0.4023(4) 0.84785(14) 0.8983(3) 0.0409(8) Uani 1 1 d . . . H23 H 0.353(4) 0.8408(16) 0.943(3) 0.053(11) Uiso 1 1 d . . . C24 C 0.5374(3) 0.82997(14) 0.9044(2) 0.0389(7) Uani 1 1 d . . . H24 H 0.590(4) 0.8093(16) 0.958(3) 0.050(10) Uiso 1 1 d . . . C25 C 0.5687(3) 0.84746(14) 0.8127(3) 0.0373(7) Uani 1 1 d . . . H25 H 0.647(3) 0.8428(14) 0.797(2) 0.040(9) Uiso 1 1 d . . . C26 C 0.4650(3) 0.75942(14) 0.6749(2) 0.0352(6) Uani 1 1 d . . . B B 0.8112(4) 0.90302(18) 0.6526(3) 0.0419(8) Uani 1 1 d . . . F1 F 0.8260(3) 0.86962(13) 0.5689(2) 0.0714(10) Uani 0.917(5) 1 d P A 1 F2 F 0.6728(2) 0.91541(13) 0.63731(18) 0.0608(8) Uani 0.917(5) 1 d P A 1 F3 F 0.8795(3) 0.95553(12) 0.6527(2) 0.0729(9) Uani 0.917(5) 1 d P A 1 F4 F 0.8609(3) 0.87463(18) 0.7441(2) 0.0856(12) Uani 0.917(5) 1 d P A 1 F1B F 0.794(3) 0.8478(15) 0.627(3) 0.078(10) Uiso 0.083(5) 1 d P A 2 F2B F 0.740(5) 0.940(2) 0.627(3) 0.108(15) Uiso 0.083(5) 1 d P A 2 F3B F 0.951(7) 0.907(3) 0.660(5) 0.17(2) Uiso 0.083(5) 1 d P A 2 F4B F 0.827(2) 0.9053(11) 0.7676(18) 0.036(6) Uiso 0.083(5) 1 d P A 2 C27 C 0.0202(4) 0.93276(18) 0.4421(3) 0.0520(9) Uani 1 1 d . . . H27A H 0.021(4) 0.9714(17) 0.411(3) 0.056(11) Uiso 1 1 d . . . H27B H -0.063(4) 0.9270(19) 0.465(3) 0.077(14) Uiso 1 1 d . . . Cl1 Cl 0.15821(9) 0.92855(4) 0.55284(7) 0.0539(2) Uani 1 1 d . . . Cl2 Cl 0.03331(12) 0.88180(5) 0.34586(8) 0.0669(3) Uani 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 Ni 0.02142(16) 0.02183(17) 0.02808(18) 0.00114(14) 0.00164(13) 0.00034(13) Fe 0.02490(19) 0.0253(2) 0.02426(19) -0.00193(15) 0.00561(15) -0.00064(15) S1 0.0243(3) 0.0263(3) 0.0345(4) -0.0013(3) 0.0039(3) 0.0015(3) S2 0.0205(3) 0.0234(3) 0.0319(3) 0.0013(3) 0.0022(3) -0.0006(2) S3 0.0275(3) 0.0245(3) 0.0277(3) 0.0013(3) 0.0005(3) 0.0026(3) S4 0.0296(3) 0.0264(3) 0.0278(3) -0.0003(3) 0.0026(3) 0.0008(3) O1 0.0730(18) 0.0714(18) 0.0435(14) -0.0135(13) 0.0309(13) 0.0019(14) C1 0.0287(14) 0.0256(15) 0.0381(16) 0.0027(12) 0.0013(12) 0.0039(12) C2 0.0241(13) 0.0265(14) 0.0374(15) 0.0028(12) 0.0009(11) 0.0041(11) C3 0.0380(18) 0.0402(19) 0.0412(18) 0.0045(15) -0.0065(15) 0.0041(16) C4 0.0256(15) 0.0392(19) 0.054(2) 0.0023(16) 0.0080(14) 0.0009(14) C5 0.0257(14) 0.0257(14) 0.0418(17) -0.0002(13) 0.0045(13) -0.0057(11) C6 0.0270(13) 0.0226(13) 0.0358(15) -0.0012(11) 0.0049(11) -0.0068(11) C7 0.0363(16) 0.0297(16) 0.0361(16) 0.0022(13) 0.0002(13) -0.0100(13) C8 0.0507(19) 0.0387(18) 0.0337(17) -0.0066(14) 0.0116(15) -0.0140(15) C9 0.0478(19) 0.0333(17) 0.050(2) -0.0109(15) 0.0171(16) -0.0030(15) C10 0.0380(17) 0.0292(16) 0.0441(18) -0.0014(14) 0.0025(14) 0.0021(13) C11 0.0367(15) 0.0208(13) 0.0317(14) 0.0008(11) 0.0051(12) -0.0049(12) C12 0.0405(17) 0.0217(14) 0.0358(16) 0.0029(12) 0.0049(13) -0.0037(13) C13 0.0325(15) 0.0308(15) 0.0305(14) 0.0010(12) -0.0041(12) 0.0065(12) C14 0.055(2) 0.0322(18) 0.0331(17) 0.0057(14) 0.0044(15) 0.0004(16) C15 0.0417(19) 0.044(2) 0.048(2) -0.0041(17) -0.0080(17) 0.0165(16) C16 0.0269(14) 0.0335(16) 0.0342(16) -0.0017(13) -0.0070(13) 0.0037(12) C21 0.0458(18) 0.0276(15) 0.0370(16) 0.0035(13) 0.0075(14) -0.0059(13) C22 0.0385(17) 0.0262(15) 0.0531(19) -0.0100(14) 0.0094(15) -0.0002(13) C23 0.052(2) 0.0367(17) 0.0392(17) -0.0127(14) 0.0211(16) -0.0129(15) C24 0.0425(17) 0.0381(17) 0.0300(15) -0.0014(13) -0.0014(13) -0.0121(14) C25 0.0318(16) 0.0361(17) 0.0435(17) -0.0029(14) 0.0092(14) -0.0097(13) C26 0.0373(16) 0.0359(16) 0.0317(15) -0.0034(13) 0.0077(13) -0.0002(13) B 0.0388(19) 0.044(2) 0.041(2) 0.0080(17) 0.0063(16) 0.0001(17) F1 0.0574(15) 0.078(2) 0.077(2) -0.0258(16) 0.0158(14) 0.0103(14) F2 0.0400(13) 0.086(2) 0.0593(15) 0.0131(13) 0.0180(11) 0.0102(13) F3 0.083(2) 0.0551(17) 0.090(2) 0.0048(14) 0.0386(16) -0.0214(14) F4 0.0653(18) 0.108(3) 0.069(2) 0.051(2) -0.0085(15) -0.0095(19) C27 0.054(2) 0.049(2) 0.052(2) 0.0030(18) 0.0126(18) 0.0080(18) Cl1 0.0465(5) 0.0585(6) 0.0532(5) -0.0038(4) 0.0068(4) -0.0035(4) Cl2 0.0868(7) 0.0542(6) 0.0546(6) -0.0110(5) 0.0094(5) -0.0039(5) _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 Ni S1 2.1670(9) . ? Ni S4 2.1717(8) . ? Ni S3 2.1803(8) . ? Ni S2 2.1807(8) . ? Fe C26 1.764(3) . ? Fe C25 2.073(3) . ? Fe C21 2.080(3) . ? Fe C24 2.086(3) . ? Fe C22 2.095(3) . ? Fe C23 2.102(3) . ? Fe S4 2.2862(9) . ? Fe S1 2.3017(9) . ? S1 C1 1.830(3) . ? S2 C5 1.833(3) . ? S2 C2 1.859(3) . ? S3 C12 1.833(3) . ? S3 C13 1.864(3) . ? S4 C16 1.831(3) . ? O1 C26 1.143(4) . ? C1 C2 1.533(4) . ? C2 C4 1.520(4) . ? C2 C3 1.524(4) . ? C5 C6 1.507(4) . ? C6 C7 1.395(4) . ? C6 C11 1.403(4) . ? C7 C8 1.379(5) . ? C8 C9 1.382(5) . ? C9 C10 1.379(5) . ? C10 C11 1.393(4) . ? C11 C12 1.498(4) . ? C13 C14 1.516(5) . ? C13 C15 1.527(4) . ? C13 C16 1.530(4) . ? C21 C22 1.405(5) . ? C21 C25 1.424(4) . ? C22 C23 1.406(5) . ? C23 C24 1.413(5) . ? C24 C25 1.400(4) . ? B F2B 1.11(5) . ? B F1B 1.30(3) . ? B F4 1.356(4) . ? B F3 1.381(5) . ? B F1 1.391(5) . ? B F2 1.396(5) . ? B F3B 1.40(6) . ? B F4B 1.50(2) . ? C27 Cl1 1.752(4) . ? C27 Cl2 1.760(4) . ? 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 S1 Ni S4 80.92(3) . . ? S1 Ni S3 168.40(3) . . ? S4 Ni S3 91.38(3) . . ? S1 Ni S2 91.02(3) . . ? S4 Ni S2 169.54(3) . . ? S3 Ni S2 95.52(3) . . ? C26 Fe C25 90.54(14) . . ? C26 Fe C21 95.03(14) . . ? C25 Fe C21 40.12(13) . . ? C26 Fe C24 121.42(14) . . ? C25 Fe C24 39.34(12) . . ? C21 Fe C24 66.69(13) . . ? C26 Fe C22 130.67(14) . . ? C25 Fe C22 66.22(13) . . ? C21 Fe C22 39.32(13) . . ? C24 Fe C22 66.08(13) . . ? C26 Fe C23 156.51(14) . . ? C25 Fe C23 66.04(13) . . ? C21 Fe C23 66.19(13) . . ? C24 Fe C23 39.45(13) . . ? C22 Fe C23 39.16(13) . . ? C26 Fe S4 96.58(10) . . ? C25 Fe S4 123.89(9) . . ? C21 Fe S4 160.38(9) . . ? C24 Fe S4 93.73(9) . . ? C22 Fe S4 132.68(10) . . ? C23 Fe S4 98.17(10) . . ? C26 Fe S1 100.31(10) . . ? C25 Fe S1 156.60(10) . . ? C21 Fe S1 117.58(9) . . ? C24 Fe S1 137.99(10) . . ? C22 Fe S1 91.28(9) . . ? C23 Fe S1 100.98(10) . . ? S4 Fe S1 75.71(3) . . ? C1 S1 Ni 101.17(10) . . ? C1 S1 Fe 116.80(10) . . ? Ni S1 Fe 82.94(3) . . ? C5 S2 C2 106.31(13) . . ? C5 S2 Ni 111.38(11) . . ? C2 S2 Ni 104.52(9) . . ? C12 S3 C13 105.35(14) . . ? C12 S3 Ni 110.28(11) . . ? C13 S3 Ni 103.99(10) . . ? C16 S4 Ni 101.25(10) . . ? C16 S4 Fe 114.63(11) . . ? Ni S4 Fe 83.21(3) . . ? C2 C1 S1 110.3(2) . . ? C4 C2 C3 111.2(3) . . ? C4 C2 C1 112.8(3) . . ? C3 C2 C1 110.8(3) . . ? C4 C2 S2 112.6(2) . . ? C3 C2 S2 108.0(2) . . ? C1 C2 S2 100.97(18) . . ? C6 C5 S2 109.16(19) . . ? C7 C6 C11 119.1(3) . . ? C7 C6 C5 118.4(3) . . ? C11 C6 C5 122.5(3) . . ? C8 C7 C6 121.0(3) . . ? C7 C8 C9 120.2(3) . . ? C10 C9 C8 119.3(3) . . ? C9 C10 C11 121.7(3) . . ? C10 C11 C6 118.7(3) . . ? C10 C11 C12 118.7(3) . . ? C6 C11 C12 122.6(3) . . ? C11 C12 S3 108.9(2) . . ? C14 C13 C15 111.9(3) . . ? C14 C13 C16 112.2(3) . . ? C15 C13 C16 110.6(3) . . ? C14 C13 S3 111.9(2) . . ? C15 C13 S3 107.9(2) . . ? C16 C13 S3 101.92(19) . . ? C13 C16 S4 110.2(2) . . ? C22 C21 C25 107.2(3) . . ? C22 C21 Fe 70.93(18) . . ? C25 C21 Fe 69.69(17) . . ? C21 C22 C23 108.6(3) . . ? C21 C22 Fe 69.75(18) . . ? C23 C22 Fe 70.67(18) . . ? C22 C23 C24 107.9(3) . . ? C22 C23 Fe 70.17(18) . . ? C24 C23 Fe 69.70(18) . . ? C25 C24 C23 107.9(3) . . ? C25 C24 Fe 69.81(18) . . ? C23 C24 Fe 70.85(18) . . ? C24 C25 C21 108.3(3) . . ? C24 C25 Fe 70.85(18) . . ? C21 C25 Fe 70.19(17) . . ? O1 C26 Fe 174.0(3) . . ? F2B B F1B 129(3) . . ? F2B B F4 135(2) . . ? F1B B F4 76.7(16) . . ? F2B B F3 68(3) . . ? F1B B F3 150.1(18) . . ? F4 B F3 110.1(3) . . ? F2B B F1 111(2) . . ? F1B B F1 45.3(17) . . ? F4 B F1 111.7(4) . . ? F3 B F1 108.2(3) . . ? F2B B F2 41(3) . . ? F1B B F2 95.6(16) . . ? F4 B F2 110.5(3) . . ? F3 B F2 108.2(3) . . ? F1 B F2 108.1(3) . . ? F2B B F3B 123(4) . . ? F1B B F3B 98(3) . . ? F4 B F3B 81(3) . . ? F3 B F3B 56(3) . . ? F1 B F3B 76(3) . . ? F2 B F3B 164(3) . . ? F2B B F4B 100(2) . . ? F1B B F4B 105.9(19) . . ? F4 B F4B 35.2(9) . . ? F3 B F4B 93.0(10) . . ? F1 B F4B 146.6(10) . . ? F2 B F4B 88.4(10) . . ? F3B B F4B 96(3) . . ? Cl1 C27 Cl2 112.4(2) . . ? _diffrn_measured_fraction_theta_max 0.944 _diffrn_reflns_theta_full 28.34 _diffrn_measured_fraction_theta_full 0.944 _refine_diff_density_max 0.532 _refine_diff_density_min -0.593 _refine_diff_density_rms 0.074