# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Prof Steve Davies' _publ_contact_author_email STEVE.DAVIES@CHEM.OX.AC.UK _publ_section_title ; Stereoselective functionalisation of cis- and trans-2-ferrocenyl-3-pivaloyl-1,3-oxazolidin-5-ones: asymmetric synthesis of (R)- and (S)-2-alkyl-2-aminopent-4-enoic acids and (2R,3S)-2-amino-2-methyl-3-hydroxy-3-phenylpropanoic acid ; _publ_author_name 'Steve Davies' # Attachment 'CCDC679348.cif' data_CRYSTALS_cif1 _database_code_depnum_ccdc_archive 'CCDC 679348' _audit_creation_date 04-11-10 _audit_creation_method CRYSTALS_ver_12-03-99 #========================================================================== _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point ? # choose from 'full, fullcycle, atomblock, userblock, diagonal, sparse' _refine_ls_matrix_type full # choose from 'heavy, direct, difmap, geom' _atom_sites_solution_primary direct # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom # choose from 'none, undef, noref, refall, refxyz, refU, constr, mixed' _refine_ls_hydrogen_treatment constr #**************************************************************************** # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et al 2001) ; _computing_publication_material ; CRYSTALS (Watkin et al 2001) ; _computing_molecular_graphics ; CAMERON (Watkin et al 1996) ; #============================================================= _cell_length_a 11.422000(1) _cell_angle_alpha 90 _cell_length_b 8.778999(1) _cell_angle_beta 107.526993(3) _cell_length_c 15.357000(1) _cell_angle_gamma 90 _cell_volume 1468.4139(2) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21 1 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,y+1/2,-z # choose from: rm (reference molecule of # known chirality), ad (anomolous # dispersion - ie. Flack param), rmad # (both rm and ad), syn (known from # synthetic pathway), unk (unknown) # or . (not applicable). _chemical_absolute_configuration unk loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 International_Tables_Vol_IV_Table_2.2B 'Fe ' 0.3463 0.8444 11.7695 4.7611 7.3573 0.3072 3.5222 15.3535 2.3045 76.8805 1.0369 International_Tables_Vol_IV_Table_2.2B 'N ' 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 International_Tables_Vol_IV_Table_2.2B 'O ' 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 International_Tables_Vol_IV_Table_2.2B _cell_formula_units_Z 2 _chemical_formula_sum ' C34 H35 Fe1 N1 O6 ' _chemical_formula_moiety ' C34 H35 Fe1 N1 O6 ' _chemical_compound_source ; ? ; _chemical_formula_weight 609.50 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 120 _exptl_crystal_description ' block ' _exptl_crystal_colour ' orange ' _exptl_crystal_size_min 0.20 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_max 0.40 _exptl_crystal_density_diffrn 1.378 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 640.000 _exptl_absorpt_coefficient_mu 0.561 # Sheldrick geometric definitions 0.85 0.89 _diffrn_measurement_device_type ; Unknown ; _diffrn_radiation_monochromator graphite _computing_data_collection ; DATA COLLECTION ; _computing_data_reduction ; USER DEFINED 5 ; _computing_cell_refinement ; USER DEFINED 6 ; _computing_structure_solution ; USER DEFINED 7 ; _diffrn_measurement_method \w/2\q _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.85 _exptl_absorpt_correction_T_max 0.89 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 120 _diffrn_reflns_number 3240 _reflns_number_total 0 _diffrn_reflns_av_R_equivalents 0.00 # Number of reflections with Friedels Law is 0 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 3094 _diffrn_reflns_theta_min 1.391 _diffrn_reflns_theta_max 26.655 _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 21.857 _diffrn_measured_fraction_theta_full 0.988 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _reflns_limit_h_min -14 _reflns_limit_h_max 13 _reflns_limit_k_min 0 _reflns_limit_k_max 11 _reflns_limit_l_min 0 _reflns_limit_l_max 19 _refine_diff_density_min -0.28 _refine_diff_density_max 0.38 _refine_ls_number_reflns 3143 _refine_ls_number_parameters 379 #_refine_ls_R_factor_ref 0.0373 _refine_ls_wR_factor_ref 0.0372 _refine_ls_goodness_of_fit_ref 1.1712 #_reflns_number_all 3235 _refine_ls_R_factor_all 0.0394 _refine_ls_wR_factor_all 0.0374 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.00u(I) _reflns_number_gt 3143 _refine_ls_R_factor_gt 0.0373 _refine_ls_wR_factor_gt 0.0372 _refine_ls_shift/su_max 0.000280 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method = Prince modified Chebychev polynomial, (Watkin, 1994) W = [weight] * [1-(deltaF/6*sigmaF)^2]^2 1.98 -0.607E-01 1.53 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 ## -------------------REFERENCES ----------------------## ## Insert your own references - in alphabetic order _publ_section_references ; User-defined data collection reference Spare 5 Spare 6 Spare 7 Watkin D.J. (1994), Acta Cryst, A50, 411-437 Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin, D.J., Prout, C.K., Carruthers, J.R., Betteridge, P.W. & Cooper R.I. (2001) CRYSTALS Issue 11. Chemical Crystallography Laboratory, OXFORD, UK. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 # Replace trailing . with the number of unfound # hydrogen atoms attaced to relavent atom 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_occupancy _atom_site_adp_type _atom_site_attached_hydrogens Fe1 Fe 1.21344(3) -0.09454(7) 0.16307(2) 0.0253 1.0000 Uani . O1 O 0.86760(18) 0.1680(3) 0.16218(14) 0.0294 1.0000 Uani . O2 O 1.01134(17) 0.0428(2) 0.26823(13) 0.0249 1.0000 Uani . O3 O 0.88746(17) 0.4871(2) 0.21406(13) 0.0241 1.0000 Uani . O4 O 0.8581(2) 0.6950(3) 0.29181(17) 0.0432 1.0000 Uani . O5 O 0.76177(19) 0.6572(3) 0.14212(14) 0.0293 1.0000 Uani . O6 O 1.24627(18) 0.4547(2) 0.36837(15) 0.0261 1.0000 Uani . N1 N 1.14504(19) 0.2348(3) 0.33177(14) 0.0174 1.0000 Uani . C1 C 0.9637(2) 0.1693(3) 0.22257(18) 0.0223 1.0000 Uani . C2 C 1.0474(2) 0.3056(3) 0.25652(17) 0.0183 1.0000 Uani . C3 C 0.9771(2) 0.4291(3) 0.29472(16) 0.0191 1.0000 Uani . C4 C 0.9173(2) 0.3648(3) 0.36190(18) 0.0196 1.0000 Uani . C5 C 0.9816(2) 0.3633(3) 0.45422(18) 0.0222 1.0000 Uani . C6 C 0.9322(3) 0.2938(3) 0.51619(18) 0.0259 1.0000 Uani . C7 C 0.8162(3) 0.2285(3) 0.4864(2) 0.0279 1.0000 Uani . C8 C 0.7502(3) 0.2345(4) 0.3943(2) 0.0293 1.0000 Uani . C9 C 0.8003(2) 0.3006(4) 0.33287(19) 0.0252 1.0000 Uani . C10 C 1.0918(2) 0.3694(3) 0.17930(18) 0.0238 1.0000 Uani . C11 C 0.8388(2) 0.6220(3) 0.22345(19) 0.0245 1.0000 Uani . C12 C 0.6979(3) 0.8022(4) 0.1378(2) 0.0364 1.0000 Uani . C13 C 0.6295(3) 0.8244(4) 0.0384(2) 0.0310 1.0000 Uani . C14 C 0.6796(3) 0.9069(6) -0.0166(2) 0.0432 1.0000 Uani . C15 C 0.6179(3) 0.9247(5) -0.1098(2) 0.0438 1.0000 Uani . C16 C 0.5057(3) 0.8580(5) -0.1462(2) 0.0440 1.0000 Uani . C17 C 0.4552(4) 0.7730(7) -0.0919(3) 0.0704 1.0000 Uani . C18 C 0.5161(3) 0.7570(6) 0.0001(3) 0.0610 1.0000 Uani . C19 C 1.1343(2) 0.0686(3) 0.32696(18) 0.0212 1.0000 Uani . C20 C 1.2401(2) 0.3200(3) 0.38674(19) 0.0194 1.0000 Uani . C21 C 1.3367(2) 0.2560(3) 0.47287(19) 0.0240 1.0000 Uani . C22 C 1.4594(3) 0.2513(4) 0.4519(2) 0.0391 1.0000 Uani . C23 C 1.3133(3) 0.1016(4) 0.5101(2) 0.0347 1.0000 Uani . C24 C 1.3454(3) 0.3739(4) 0.5485(2) 0.0374 1.0000 Uani . C25 C 1.2272(3) -0.0076(4) 0.2904(2) 0.0237 1.0000 Uani . C26 C 1.2491(4) -0.1686(4) 0.2941(2) 0.0339 1.0000 Uani . C27 C 1.3500(4) -0.1977(5) 0.2618(2) 0.0433 1.0000 Uani . C28 C 1.3909(3) -0.0561(5) 0.2373(2) 0.0408 1.0000 Uani . C29 C 1.3165(3) 0.0609(4) 0.2544(2) 0.0290 1.0000 Uani . C30 C 1.0526(4) -0.0283(6) 0.0701(3) 0.0484 1.0000 Uani . C31 C 1.0522(5) -0.1829(7) 0.0842(3) 0.0605 1.0000 Uani . C32 C 1.1454(6) -0.2465(6) 0.0623(3) 0.0726 1.0000 Uani . C33 C 1.2102(4) -0.135(1) 0.0340(3) 0.0894 1.0000 Uani . C34 C 1.1507(5) 0.0057(6) 0.0375(3) 0.0612 1.0000 Uani . H31 H 1.0287 0.5150 0.3288 0.0184 1.0000 Uiso . H51 H 1.0641 0.4120 0.4762 0.0213 1.0000 Uiso . H61 H 0.9800 0.2915 0.5822 0.0257 1.0000 Uiso . H71 H 0.7805 0.1774 0.5311 0.0291 1.0000 Uiso . H81 H 0.6662 0.1901 0.3729 0.0306 1.0000 Uiso . H91 H 0.7525 0.3034 0.2668 0.0240 1.0000 Uiso . H101 H 1.1364 0.2883 0.1569 0.0258 1.0000 Uiso . H102 H 1.1485 0.4571 0.2035 0.0258 1.0000 Uiso . H103 H 1.0197 0.4051 0.1290 0.0258 1.0000 Uiso . H121 H 0.7581 0.8869 0.1602 0.0346 1.0000 Uiso . H122 H 0.6397 0.7982 0.1747 0.0346 1.0000 Uiso . H141 H 0.7613 0.9559 0.0098 0.0389 1.0000 Uiso . H151 H 0.6562 0.9844 -0.1497 0.0417 1.0000 Uiso . H161 H 0.4603 0.8722 -0.2124 0.0382 1.0000 Uiso . H171 H 0.3737 0.7213 -0.1191 0.0573 1.0000 Uiso . H181 H 0.4779 0.6973 0.0397 0.0520 1.0000 Uiso . H191 H 1.1483 0.0247 0.3895 0.0197 1.0000 Uiso . H221 H 1.5241 0.2111 0.5059 0.0350 1.0000 Uiso . H222 H 1.4815 0.3577 0.4383 0.0350 1.0000 Uiso . H223 H 1.4516 0.1853 0.3977 0.0350 1.0000 Uiso . H231 H 1.3827 0.0751 0.5649 0.0310 1.0000 Uiso . H232 H 1.3045 0.0216 0.4620 0.0310 1.0000 Uiso . H233 H 1.2350 0.1065 0.5272 0.0310 1.0000 Uiso . H241 H 1.4076 0.3381 0.6059 0.0335 1.0000 Uiso . H242 H 1.3722 0.4736 0.5295 0.0335 1.0000 Uiso . H243 H 1.2640 0.3847 0.5585 0.0335 1.0000 Uiso . H261 H 1.2016 -0.2466 0.3171 0.0288 1.0000 Uiso . H271 H 1.3857 -0.3002 0.2573 0.0364 1.0000 Uiso . H281 H 1.4605 -0.0417 0.2118 0.0335 1.0000 Uiso . H291 H 1.3244 0.1724 0.2429 0.0268 1.0000 Uiso . H301 H 0.9892 0.0425 0.0810 0.0402 1.0000 Uiso . H311 H 0.9919 -0.2408 0.1066 0.0509 1.0000 Uiso . H321 H 1.1674 -0.3573 0.0667 0.0617 1.0000 Uiso . H331 H 1.2857 -0.1476 0.0129 0.0527 1.0000 Uiso . H341 H 1.1787 0.1093 0.0219 0.0467 1.0000 Uiso . 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 0.02631(18) 0.02597(19) 0.01775(17) -0.00497(18) -0.00201(13) 0.00808(19) O1 0.0211(9) 0.0362(11) 0.025(1) -0.0069(9) -0.0022(8) -0.0017(8) O2 0.0202(9) 0.025(1) 0.025(1) -0.0005(8) -0.0001(7) -0.0064(8) O3 0.0236(9) 0.027(1) 0.0202(9) 0.0046(8) 0.0040(8) 0.0065(8) O4 0.0499(14) 0.0297(12) 0.0350(12) -0.005(1) -0.0099(11) 0.0134(11) O5 0.028(1) 0.0302(11) 0.025(1) 0.0025(9) -0.0006(8) 0.0101(9) O6 0.0217(9) 0.019(1) 0.0339(11) 0.0005(8) 0.0028(8) -0.0032(7) N1 0.0156(9) 0.017(1) 0.018(1) 0.0010(8) 0.0022(8) 0.0021(8) C1 0.0208(12) 0.0251(13) 0.0217(12) -0.0041(11) 0.008(1) -0.001(1) C2 0.0155(11) 0.0223(12) 0.0166(11) 0.002(1) 0.0039(9) 0.002(1) C3 0.017(1) 0.0186(14) 0.019(1) 0.002(1) 0.0013(8) 0.004(1) C4 0.0196(11) 0.0202(13) 0.0189(11) 0.0008(9) 0.0055(9) 0.0040(9) C5 0.0196(11) 0.0233(13) 0.0221(13) -0.0010(9) 0.004(1) 0.0037(9) C6 0.0328(14) 0.0253(13) 0.0199(13) 0.001(1) 0.0086(11) 0.0099(11) C7 0.0349(15) 0.0249(14) 0.0290(14) 0.0025(12) 0.0175(12) 0.0004(12) C8 0.0255(13) 0.0313(15) 0.0332(15) -0.0041(12) 0.0120(12) -0.0044(12) C9 0.0180(12) 0.0329(14) 0.0235(13) -0.0034(12) 0.004(1) -0.0024(11) C10 0.0216(12) 0.0279(16) 0.0226(12) 0.006(1) 0.008(1) 0.003(1) C11 0.0181(12) 0.0278(14) 0.0240(13) 0.0034(11) 0.001(1) 0.002(1) C12 0.0347(15) 0.0347(16) 0.0333(16) 0.0045(13) 0.0005(13) 0.0161(14) C13 0.0258(13) 0.0278(15) 0.0329(16) 0.0031(12) -0.0011(12) 0.0099(12) C14 0.0274(13) 0.0436(17) 0.0483(17) 0.014(2) -0.0043(12) -0.0045(18) C15 0.0301(14) 0.053(2) 0.0440(17) 0.0155(19) 0.0047(13) -0.0031(17) C16 0.0330(15) 0.061(2) 0.0298(16) 0.0070(15) -0.0026(13) 0.0008(15) C17 0.038(2) 0.108(4) 0.048(2) 0.025(3) -0.0136(18) -0.030(2) C18 0.0317(18) 0.099(4) 0.044(2) 0.031(2) -0.0012(16) -0.013(2) C19 0.0212(12) 0.0187(12) 0.0198(12) -0.001(1) 0.000(1) -0.003(1) C20 0.0161(11) 0.0189(13) 0.0227(13) 0.001(1) 0.005(1) 0.001(1) C21 0.0176(12) 0.0214(13) 0.0264(14) -0.0046(11) -0.003(1) 0.001(1) C22 0.0192(13) 0.048(2) 0.0426(18) -0.0062(16) -0.0023(12) 0.0048(13) C23 0.0384(16) 0.0299(15) 0.0237(14) 0.0031(12) -0.0086(12) -0.0011(13) C24 0.0312(14) 0.037(2) 0.0324(15) -0.0112(13) -0.0086(12) 0.0088(12) C25 0.0261(14) 0.0223(13) 0.0161(13) -0.004(1) -0.0034(11) 0.0026(11) C26 0.053(2) 0.0221(15) 0.0170(15) -0.0001(12) -0.0037(14) 0.0096(14) C27 0.050(2) 0.0401(19) 0.0239(16) -0.0089(14) -0.0130(15) 0.0271(17) C28 0.0222(13) 0.062(3) 0.0303(15) -0.0186(15) -0.0036(11) 0.0136(14) C29 0.0206(13) 0.0382(17) 0.0243(14) -0.0097(13) 0.0007(11) -0.0022(12) C30 0.0413(19) 0.070(3) 0.0204(16) -0.0127(16) -0.0105(14) 0.0276(19) C31 0.054(2) 0.083(4) 0.030(2) 0.009(2) -0.0103(18) -0.034(3) C32 0.091(4) 0.044(2) 0.046(3) -0.022(2) -0.035(3) 0.027(2) C33 0.0299(17) 0.208(9) 0.0224(17) -0.054(3) -0.0044(14) 0.027(3) C34 0.080(3) 0.064(3) 0.0215(18) 0.0111(18) -0.012(2) -0.033(3) _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Fe1 . C25 . 2.061(3) yes Fe1 . C26 . 2.035(3) yes Fe1 . C27 . 2.032(3) yes Fe1 . C28 . 2.032(3) yes Fe1 . C29 . 2.054(3) yes Fe1 . C30 . 2.042(4) yes Fe1 . C31 . 2.029(4) yes Fe1 . C32 . 2.013(4) yes Fe1 . C33 . 2.002(4) yes Fe1 . C34 . 2.043(4) yes O1 . C1 . 1.205(3) yes O2 . C1 . 1.338(3) yes O2 . C19 . 1.440(3) yes O3 . C3 . 1.442(3) yes O3 . C11 . 1.334(4) yes O4 . C11 . 1.193(4) yes O5 . C11 . 1.330(3) yes O5 . C12 . 1.459(4) yes O6 . C20 . 1.223(4) yes N1 . C2 . 1.479(3) yes N1 . C19 . 1.464(3) yes N1 . C20 . 1.378(3) yes C1 . C2 . 1.522(4) yes C2 . C3 . 1.565(3) yes C2 . C10 . 1.530(3) yes C3 . C4 . 1.508(4) yes C3 . H31 . 1.002 no C4 . C5 . 1.386(4) yes C4 . C9 . 1.395(4) yes C5 . C6 . 1.386(4) yes C5 . H51 . 0.996 no C6 . C7 . 1.389(4) yes C6 . H61 . 0.997 no C7 . C8 . 1.389(4) yes C7 . H71 . 1.004 no C8 . C9 . 1.370(4) yes C8 . H81 . 0.995 no C9 . H91 . 0.997 no C10 . H101 . 0.995 no C10 . H102 . 1.003 no C10 . H103 . 0.995 no C12 . C13 . 1.503(4) yes C12 . H121 . 1.001 no C12 . H122 . 0.996 no C13 . C14 . 1.363(5) yes C13 . C18 . 1.384(5) yes C14 . C15 . 1.401(4) yes C14 . H141 . 0.996 no C15 . C16 . 1.365(5) yes C15 . H151 . 1.001 no C16 . C17 . 1.369(6) yes C16 . H161 . 1.001 no C17 . C18 . 1.382(6) yes C17 . H171 . 1.006 no C18 . H181 . 0.997 no C19 . C25 . 1.499(4) yes C19 . H191 . 1.002 no C20 . C21 . 1.550(4) yes C21 . C22 . 1.530(4) yes C21 . C23 . 1.525(4) yes C21 . C24 . 1.537(4) yes C22 . H221 . 0.994 no C22 . H222 . 1.006 no C22 . H223 . 0.995 no C23 . H231 . 0.995 no C23 . H232 . 1.002 no C23 . H233 . 1.006 no C24 . H241 . 1.001 no C24 . H242 . 0.999 no C24 . H243 . 0.991 no C25 . C26 . 1.434(4) yes C25 . C29 . 1.431(5) yes C26 . C27 . 1.409(6) yes C26 . H261 . 1.002 no C27 . C28 . 1.418(6) yes C27 . H271 . 0.999 no C28 . C29 . 1.407(5) yes C28 . H281 . 0.995 no C29 . H291 . 1.004 no C30 . C31 . 1.374(7) yes C30 . C34 . 1.391(7) yes C30 . H301 . 1.006 no C31 . C32 . 1.331(9) yes C31 . H311 . 0.997 no C32 . C33 . 1.376(9) yes C32 . H321 . 1.002 no C33 . C34 . 1.416(9) yes C33 . H331 . 1.015 no C34 . H341 . 1.016 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C25 . Fe1 . C26 . 41.0(1) yes C25 . Fe1 . C27 . 68.60(13) yes C26 . Fe1 . C27 . 40.54(17) yes C25 . Fe1 . C28 . 68.16(13) yes C26 . Fe1 . C28 . 68.26(16) yes C27 . Fe1 . C28 . 40.83(18) yes C25 . Fe1 . C29 . 40.69(13) yes C26 . Fe1 . C29 . 68.54(14) yes C27 . Fe1 . C29 . 68.48(16) yes C28 . Fe1 . C29 . 40.27(13) yes C25 . Fe1 . C30 . 110.68(14) yes C26 . Fe1 . C30 . 130.68(18) yes C27 . Fe1 . C30 . 167.3(2) yes C28 . Fe1 . C30 . 151.64(19) yes C29 . Fe1 . C30 . 119.86(16) yes C25 . Fe1 . C31 . 120.28(19) yes C26 . Fe1 . C31 . 110.09(17) yes C27 . Fe1 . C31 . 129.1(2) yes C28 . Fe1 . C31 . 166.2(2) yes C29 . Fe1 . C31 . 153.1(2) yes C25 . Fe1 . C32 . 151.2(2) yes C26 . Fe1 . C32 . 117.6(2) yes C27 . Fe1 . C32 . 108.06(16) yes C28 . Fe1 . C32 . 129.1(2) yes C29 . Fe1 . C32 . 166.9(2) yes C25 . Fe1 . C33 . 167.9(3) yes C26 . Fe1 . C33 . 149.4(3) yes C27 . Fe1 . C33 . 116.19(19) yes C28 . Fe1 . C33 . 107.62(15) yes C29 . Fe1 . C33 . 129.0(2) yes C25 . Fe1 . C34 . 129.85(19) yes C26 . Fe1 . C34 . 168.4(2) yes C27 . Fe1 . C34 . 150.3(2) yes C28 . Fe1 . C34 . 117.71(18) yes C29 . Fe1 . C34 . 108.92(16) yes C30 . Fe1 . C31 . 39.5(2) yes C30 . Fe1 . C32 . 66.03(18) yes C31 . Fe1 . C32 . 38.5(3) yes C30 . Fe1 . C33 . 67.27(17) yes C31 . Fe1 . C33 . 66.3(2) yes C32 . Fe1 . C33 . 40.1(3) yes C30 . Fe1 . C34 . 39.8(2) yes C31 . Fe1 . C34 . 66.67(18) yes C32 . Fe1 . C34 . 67.4(2) yes C33 . Fe1 . C34 . 41.0(3) yes C1 . O2 . C19 . 111.3(2) yes C3 . O3 . C11 . 115.6(2) yes C11 . O5 . C12 . 115.2(2) yes C2 . N1 . C19 . 110.3(2) yes C2 . N1 . C20 . 121.4(2) yes C19 . N1 . C20 . 127.6(2) yes O1 . C1 . O2 . 121.9(3) yes O1 . C1 . C2 . 127.1(3) yes O2 . C1 . C2 . 111.0(2) yes N1 . C2 . C1 . 100.7(2) yes N1 . C2 . C3 . 110.4(2) yes C1 . C2 . C3 . 109.4(2) yes N1 . C2 . C10 . 114.3(2) yes C1 . C2 . C10 . 110.1(2) yes C3 . C2 . C10 . 111.4(2) yes O3 . C3 . C2 . 103.58(19) yes O3 . C3 . C4 . 111.7(2) yes C2 . C3 . C4 . 112.8(2) yes O3 . C3 . H31 . 109.651 no C2 . C3 . H31 . 115.446 no C4 . C3 . H31 . 103.919 no C3 . C4 . C5 . 119.6(2) yes C3 . C4 . C9 . 121.4(2) yes C5 . C4 . C9 . 119.0(2) yes C4 . C5 . C6 . 120.5(3) yes C4 . C5 . H51 . 119.839 no C6 . C5 . H51 . 119.706 no C5 . C6 . C7 . 120.1(3) yes C5 . C6 . H61 . 119.697 no C7 . C6 . H61 . 120.226 no C6 . C7 . C8 . 119.4(3) yes C6 . C7 . H71 . 120.158 no C8 . C7 . H71 . 120.448 no C7 . C8 . C9 . 120.4(3) yes C7 . C8 . H81 . 119.616 no C9 . C8 . H81 . 119.962 no C4 . C9 . C8 . 120.6(3) yes C4 . C9 . H91 . 119.547 no C8 . C9 . H91 . 119.813 no C2 . C10 . H101 . 109.289 no C2 . C10 . H102 . 108.753 no H101 . C10 . H102 . 109.688 no C2 . C10 . H103 . 109.084 no H101 . C10 . H103 . 110.329 no H102 . C10 . H103 . 109.670 no O3 . C11 . O4 . 126.8(3) yes O3 . C11 . O5 . 106.5(2) yes O4 . C11 . O5 . 126.6(3) yes O5 . C12 . C13 . 105.0(3) yes O5 . C12 . H121 . 110.499 no C13 . C12 . H121 . 110.273 no O5 . C12 . H122 . 110.734 no C13 . C12 . H122 . 110.508 no H121 . C12 . H122 . 109.749 no C12 . C13 . C14 . 120.8(3) yes C12 . C13 . C18 . 120.7(3) yes C14 . C13 . C18 . 118.5(3) yes C13 . C14 . C15 . 121.2(3) yes C13 . C14 . H141 . 119.551 no C15 . C14 . H141 . 119.289 no C14 . C15 . C16 . 119.4(3) yes C14 . C15 . H151 . 120.320 no C16 . C15 . H151 . 120.269 no C15 . C16 . C17 . 120.1(3) yes C15 . C16 . H161 . 119.856 no C17 . C16 . H161 . 120.090 no C16 . C17 . C18 . 120.2(4) yes C16 . C17 . H171 . 120.041 no C18 . C17 . H171 . 119.749 no C13 . C18 . C17 . 120.7(4) yes C13 . C18 . H181 . 119.399 no C17 . C18 . H181 . 119.942 no O2 . C19 . N1 . 103.9(2) yes O2 . C19 . C25 . 111.2(2) yes N1 . C19 . C25 . 113.9(2) yes O2 . C19 . H191 . 112.550 no N1 . C19 . H191 . 110.391 no C25 . C19 . H191 . 105.099 no O6 . C20 . N1 . 118.2(3) yes O6 . C20 . C21 . 118.2(3) yes N1 . C20 . C21 . 123.6(2) yes C20 . C21 . C22 . 107.0(2) yes C20 . C21 . C23 . 118.8(2) yes C22 . C21 . C23 . 109.3(3) yes C20 . C21 . C24 . 105.5(2) yes C22 . C21 . C24 . 108.8(2) yes C23 . C21 . C24 . 107.1(3) yes C21 . C22 . H221 . 109.368 no C21 . C22 . H222 . 108.764 no H221 . C22 . H222 . 109.447 no C21 . C22 . H223 . 109.555 no H221 . C22 . H223 . 110.320 no H222 . C22 . H223 . 109.363 no C21 . C23 . H231 . 109.886 no C21 . C23 . H232 . 109.688 no H231 . C23 . H232 . 109.715 no C21 . C23 . H233 . 109.281 no H231 . C23 . H233 . 109.422 no H232 . C23 . H233 . 108.830 no C21 . C24 . H241 . 108.707 no C21 . C24 . H242 . 108.912 no H241 . C24 . H242 . 109.442 no C21 . C24 . H243 . 109.368 no H241 . C24 . H243 . 110.128 no H242 . C24 . H243 . 110.252 no Fe1 . C25 . C19 . 131.3(2) yes Fe1 . C25 . C26 . 68.5(2) yes C19 . C25 . C26 . 124.1(3) yes Fe1 . C25 . C29 . 69.40(18) yes C19 . C25 . C29 . 128.7(3) yes C26 . C25 . C29 . 107.0(3) yes Fe1 . C26 . C25 . 70.5(2) yes Fe1 . C26 . C27 . 69.6(2) yes C25 . C26 . C27 . 108.5(4) yes Fe1 . C26 . H261 . 126.784 no C25 . C26 . H261 . 125.551 no C27 . C26 . H261 . 125.962 no Fe1 . C27 . C26 . 69.86(19) yes Fe1 . C27 . C28 . 69.61(19) yes C26 . C27 . C28 . 107.7(3) yes Fe1 . C27 . H271 . 125.978 no C26 . C27 . H271 . 125.615 no C28 . C27 . H271 . 126.700 no Fe1 . C28 . C27 . 69.6(2) yes Fe1 . C28 . C29 . 70.70(17) yes C27 . C28 . C29 . 109.0(3) yes Fe1 . C28 . H281 . 125.466 no C27 . C28 . H281 . 125.576 no C29 . C28 . H281 . 125.463 no Fe1 . C29 . C25 . 69.91(18) yes Fe1 . C29 . C28 . 69.02(18) yes C25 . C29 . C28 . 107.9(3) yes Fe1 . C29 . H291 . 126.254 no C25 . C29 . H291 . 126.166 no C28 . C29 . H291 . 125.972 no Fe1 . C30 . C31 . 69.7(3) yes Fe1 . C30 . C34 . 70.1(2) yes C31 . C30 . C34 . 108.0(5) yes Fe1 . C30 . H301 . 126.927 no C31 . C30 . H301 . 123.171 no C34 . C30 . H301 . 128.773 no Fe1 . C31 . C30 . 70.8(3) yes Fe1 . C31 . C32 . 70.1(3) yes C30 . C31 . C32 . 109.5(5) yes Fe1 . C31 . H311 . 125.886 no C30 . C31 . H311 . 126.363 no C32 . C31 . H311 . 124.119 no Fe1 . C32 . C31 . 71.4(3) yes Fe1 . C32 . C33 . 69.5(3) yes C31 . C32 . C33 . 109.1(5) yes Fe1 . C32 . H321 . 124.097 no C31 . C32 . H321 . 126.467 no C33 . C32 . H321 . 124.431 no Fe1 . C33 . C32 . 70.4(3) yes Fe1 . C33 . C34 . 71.1(2) yes C32 . C33 . C34 . 107.4(4) yes Fe1 . C33 . H331 . 124.835 no C32 . C33 . H331 . 127.634 no C34 . C33 . H331 . 124.938 no Fe1 . C34 . C30 . 70.1(2) yes Fe1 . C34 . C33 . 68.0(3) yes C30 . C34 . C33 . 105.9(4) yes Fe1 . C34 . H341 . 124.201 no C30 . C34 . H341 . 128.460 no C33 . C34 . H341 . 125.545 no # Attachment 'CCDC679349.cif' data_CRYSTALS_cif _database_code_depnum_ccdc_archive 'CCDC 679349' _audit_creation_date 04-11-10 _audit_creation_method CRYSTALS_ver_12-03-99 #========================================================================== _chemical_name_systematic # IUPAC name, in full ? _chemical_melting_point ? # choose from 'full, fullcycle, atomblock, userblock, diagonal, sparse' _refine_ls_matrix_type full # choose from 'heavy, direct, difmap, geom' _atom_sites_solution_primary direct # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom # choose from 'none, undef, noref, refall, refxyz, refU, constr, mixed' _refine_ls_hydrogen_treatment constr #**************************************************************************** # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et al 2001) ; _computing_publication_material ; CRYSTALS (Watkin et al 2001) ; _computing_molecular_graphics ; CAMERON (Watkin et al 1996) ; #============================================================= _cell_length_a 9.462(1) _cell_angle_alpha 73.144(3) _cell_length_b 10.432(1) _cell_angle_beta 85.380(3) _cell_length_c 11.673(1) _cell_angle_gamma 65.358(3) _cell_volume 1001.20837(7) _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z # choose from: rm (reference molecule of # known chirality), ad (anomolous # dispersion - ie. Flack param), rmad # (both rm and ad), syn (known from # synthetic pathway), unk (unknown) # or . (not applicable). _chemical_absolute_configuration . loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 International_Tables_Vol_IV_Table_2.2B 'O ' 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 International_Tables_Vol_IV_Table_2.2B 'N ' 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 International_Tables_Vol_IV_Table_2.2B 'Fe ' 0.3463 0.8444 11.7695 4.7611 7.3573 0.3072 3.5222 15.3535 2.3045 76.8805 1.0369 International_Tables_Vol_IV_Table_2.2B _cell_formula_units_Z 2 _chemical_formula_sum 'C23 H29 Fe N O3' _chemical_formula_moiety 'C23 H29 Fe N O3' _chemical_compound_source ? _chemical_formula_weight 423.3 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 100 _exptl_crystal_description ' block ' _exptl_crystal_colour ' yellow ' _exptl_crystal_size_min 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_max 0.25 _exptl_crystal_density_diffrn 1.404 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 448.000 _exptl_absorpt_coefficient_mu 0.777 # Sheldrick geometric definitions 0.86 0.86 _diffrn_measurement_device_type ; Unknown ; _diffrn_radiation_monochromator graphite _computing_data_collection ; DATA COLLECTION ; _computing_data_reduction ; USER DEFINED 5 ; _computing_cell_refinement ; USER DEFINED 6 ; _computing_structure_solution ; USER DEFINED 7 ; _diffrn_measurement_method \w/2\q _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.86 _exptl_absorpt_correction_T_max 0.86 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 100 _diffrn_reflns_number 3343 _reflns_number_total 3343 _diffrn_reflns_av_R_equivalents 0.04 # Number of reflections with Friedels Law is 3343 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 4261 _diffrn_reflns_theta_min 2.239 _diffrn_reflns_theta_max 26.751 _diffrn_measured_fraction_theta_max 0.785 _diffrn_reflns_theta_full 21.200 _diffrn_measured_fraction_theta_full 0.809 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _reflns_limit_h_min -11 _reflns_limit_h_max 11 _reflns_limit_k_min -12 _reflns_limit_k_max 13 _reflns_limit_l_min 0 _reflns_limit_l_max 13 _refine_diff_density_min -0.55 _refine_diff_density_max 0.40 _refine_ls_number_reflns 2799 _refine_ls_number_parameters 253 #_refine_ls_R_factor_ref 0.0488 _refine_ls_wR_factor_ref 0.0463 _refine_ls_goodness_of_fit_ref 1.1009 #_reflns_number_all 3343 _refine_ls_R_factor_all 0.0860 _refine_ls_wR_factor_all 0.0513 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>4.00u(I) _reflns_number_gt 2799 _refine_ls_R_factor_gt 0.0488 _refine_ls_wR_factor_gt 0.0463 _refine_ls_shift/su_max 0.000392 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method = Prince modified Chebychev polynomial, (Watkin, 1994) W = [weight] * [1-(deltaF/6*sigmaF)^2]^2 2.12 -0.395 1.76 ; _diffrn_radiation_probe ? _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 ## -------------------REFERENCES ----------------------## ## Insert your own references - in alphabetic order _publ_section_references ; User-defined data collection reference Spare 5 Spare 6 Spare 7 Watkin D.J. (1994), Acta Cryst, A50, 411-437 Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin, D.J., Prout, C.K., Carruthers, J.R., Betteridge, P.W. & Cooper R.I. (2001) CRYSTALS Issue 11. Chemical Crystallography Laboratory, OXFORD, UK. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 # Replace trailing . with the number of unfound # hydrogen atoms attaced to relavent atom 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_occupancy _atom_site_adp_type _atom_site_attached_hydrogens Fe1 Fe 0.25754(4) 0.30042(4) 0.67692(4) 0.0135 1.0000 Uani . O1 O 0.7610(2) 0.1769(2) 0.8122(2) 0.0231 1.0000 Uani . O2 O 0.5842(2) 0.08520(19) 0.87277(18) 0.0168 1.0000 Uani . O3 O 0.7690(2) -0.2534(2) 0.67089(19) 0.0209 1.0000 Uani . N1 N 0.6537(2) -0.0888(2) 0.7732(2) 0.0149 1.0000 Uani . C1 C 0.7043(3) 0.0962(3) 0.8054(3) 0.0164 1.0000 Uani . C2 C 0.7519(3) -0.0072(3) 0.7259(2) 0.0145 1.0000 Uani . C3 C 0.9285(3) -0.1029(3) 0.7473(3) 0.0177 1.0000 Uani . C4 C 0.9768(3) -0.2030(3) 0.8719(3) 0.0234 1.0000 Uani . C5 C 1.0542(3) -0.1834(4) 0.9499(3) 0.0301 1.0000 Uani . C6 C 0.7093(3) 0.0802(3) 0.5930(2) 0.0170 1.0000 Uani . C7 C 0.7993(3) 0.1722(3) 0.5378(3) 0.0250 1.0000 Uani . C8 C 0.5267(3) -0.0066(3) 0.8384(2) 0.0151 1.0000 Uani . C9 C 0.6794(3) -0.2179(3) 0.7490(3) 0.0171 1.0000 Uani . C10 C 0.6073(3) -0.3209(3) 0.8247(3) 0.0192 1.0000 Uani . C11 C 0.6633(4) -0.3701(3) 0.9565(3) 0.0276 1.0000 Uani . C12 C 0.6721(4) -0.4604(3) 0.7817(3) 0.0281 1.0000 Uani . C13 C 0.4295(3) -0.2553(4) 0.8127(3) 0.0321 1.0000 Uani . C14 C 0.3721(3) 0.0828(3) 0.7681(2) 0.0152 1.0000 Uani . C15 C 0.3371(3) 0.0985(3) 0.6479(3) 0.0161 1.0000 Uani . C16 C 0.1717(3) 0.1732(3) 0.6266(3) 0.0184 1.0000 Uani . C17 C 0.1056(3) 0.2038(3) 0.7348(3) 0.0189 1.0000 Uani . C18 C 0.2285(3) 0.1485(3) 0.8226(2) 0.0171 1.0000 Uani . C19 C 0.3846(3) 0.4187(3) 0.6802(3) 0.0284 1.0000 Uani . C20 C 0.3594(3) 0.4231(3) 0.5614(3) 0.0236 1.0000 Uani . C21 C 0.1975(3) 0.4859(3) 0.5358(3) 0.0188 1.0000 Uani . C22 C 0.1209(3) 0.5212(3) 0.6396(3) 0.0203 1.0000 Uani . C23 C 0.2377(4) 0.4790(3) 0.7296(3) 0.0254 1.0000 Uani . H31 H 0.9831 -0.0360 0.7299 0.0177 1.0000 Uiso . H32 H 0.9610 -0.1648 0.6905 0.0177 1.0000 Uiso . H41 H 0.9492 -0.2895 0.8977 0.0204 1.0000 Uiso . H51 H 1.0836 -0.2541 1.0318 0.0267 1.0000 Uiso . H52 H 1.0837 -0.0980 0.9267 0.0267 1.0000 Uiso . H61 H 0.5961 0.1475 0.5859 0.0170 1.0000 Uiso . H62 H 0.7283 0.0083 0.5463 0.0170 1.0000 Uiso . H71 H 0.7635 0.2246 0.4517 0.0248 1.0000 Uiso . H72 H 0.7809 0.2464 0.5821 0.0248 1.0000 Uiso . H73 H 0.9131 0.1073 0.5424 0.0248 1.0000 Uiso . H81 H 0.5055 -0.0760 0.9096 0.0160 1.0000 Uiso . H111 H 0.6162 -0.4371 1.0051 0.0283 1.0000 Uiso . H112 H 0.7794 -0.4236 0.9630 0.0283 1.0000 Uiso . H113 H 0.6313 -0.2821 0.9866 0.0283 1.0000 Uiso . H121 H 0.6280 -0.5304 0.8289 0.0292 1.0000 Uiso . H122 H 0.7883 -0.5080 0.7932 0.0292 1.0000 Uiso . H123 H 0.6427 -0.4329 0.6947 0.0292 1.0000 Uiso . H131 H 0.3908 -0.3278 0.8641 0.0312 1.0000 Uiso . H132 H 0.3852 -0.1633 0.8388 0.0312 1.0000 Uiso . H133 H 0.3957 -0.2312 0.7272 0.0312 1.0000 Uiso . H151 H 0.4143 0.0636 0.5881 0.0175 1.0000 Uiso . H161 H 0.1133 0.1991 0.5497 0.0200 1.0000 Uiso . H171 H -0.0076 0.2555 0.7469 0.0192 1.0000 Uiso . H181 H 0.2168 0.1541 0.9069 0.0171 1.0000 Uiso . H191 H 0.4878 0.3796 0.7228 0.0256 1.0000 Uiso . H201 H 0.4423 0.3878 0.5050 0.0221 1.0000 Uiso . H211 H 0.1453 0.5028 0.4584 0.0186 1.0000 Uiso . H221 H 0.0061 0.5675 0.6477 0.0181 1.0000 Uiso . H231 H 0.2192 0.4900 0.8123 0.0234 1.0000 Uiso . 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 0.01256(18) 0.01170(18) 0.0160(2) -0.00295(13) -0.00053(12) -0.00509(13) O1 0.0226(9) 0.021(1) 0.0317(13) -0.0128(8) 0.0017(8) -0.0109(8) O2 0.0162(8) 0.0170(9) 0.0195(11) -0.0071(7) 0.0023(7) -0.0080(7) O3 0.0244(9) 0.0184(9) 0.0219(11) -0.0106(8) 0.0081(8) -0.0088(7) N1 0.0139(9) 0.015(1) 0.0163(12) -0.0055(8) 0.0039(8) -0.0066(8) C1 0.0127(11) 0.0151(11) 0.0193(15) -0.005(1) -0.0012(9) -0.0034(9) C2 0.0150(11) 0.0123(11) 0.0177(15) -0.0041(9) 0.0020(9) -0.0073(9) C3 0.0138(11) 0.0186(12) 0.0205(15) -0.005(1) 0.0010(9) -0.0065(9) C4 0.0148(11) 0.0238(13) 0.0228(17) -0.0006(11) -0.000(1) -0.004(1) C5 0.0189(13) 0.0386(17) 0.0245(17) -0.0108(13) 0.0005(11) -0.0026(12) C6 0.0186(12) 0.0171(12) 0.0148(14) -0.0007(9) -0.001(1) -0.009(1) C7 0.0301(14) 0.0231(14) 0.0219(17) 0.0011(11) -0.0022(11) -0.0155(12) C8 0.0169(11) 0.0148(11) 0.0151(14) -0.0057(9) 0.0047(9) -0.0076(9) C9 0.0193(12) 0.0141(11) 0.0169(15) -0.002(1) -0.002(1) -0.007(1) C10 0.0234(13) 0.0153(12) 0.0220(15) -0.006(1) 0.004(1) -0.011(1) C11 0.0365(16) 0.0222(13) 0.0262(18) -0.0037(12) 0.0005(12) -0.0159(12) C12 0.0390(16) 0.0190(14) 0.0319(19) -0.0111(12) 0.0063(13) -0.0155(12) C13 0.0234(14) 0.0256(15) 0.049(2) -0.0050(13) 0.0015(13) -0.0151(12) C14 0.0140(11) 0.0148(11) 0.0188(15) -0.005(1) 0.002(1) -0.0081(9) C15 0.0168(11) 0.0156(11) 0.0195(15) -0.008(1) 0.003(1) -0.0084(9) C16 0.0175(12) 0.0176(12) 0.0239(16) -0.007(1) -0.002(1) -0.009(1) C17 0.0182(12) 0.0176(12) 0.0225(16) -0.005(1) 0.004(1) -0.010(1) C18 0.0189(12) 0.0166(11) 0.0153(14) -0.0021(9) 0.001(1) -0.009(1) C19 0.0226(13) 0.0168(13) 0.045(2) -0.0023(12) -0.0105(12) -0.0090(11) C20 0.0208(13) 0.0161(12) 0.0317(18) -0.0016(11) 0.0036(11) -0.009(1) C21 0.0199(12) 0.0153(11) 0.0193(16) -0.001(1) -0.000(1) -0.0079(9) C22 0.0188(12) 0.0112(11) 0.0268(16) -0.003(1) -0.001(1) -0.0038(9) C23 0.0362(15) 0.0116(12) 0.0285(18) -0.0045(11) -0.0072(12) -0.0092(11) _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Fe1 . C14 . 2.048(2) yes Fe1 . C15 . 2.041(3) yes Fe1 . C16 . 2.048(3) yes Fe1 . C17 . 2.048(3) yes Fe1 . C18 . 2.050(3) yes Fe1 . C19 . 2.059(3) yes Fe1 . C20 . 2.050(3) yes Fe1 . C21 . 2.041(3) yes Fe1 . C22 . 2.047(3) yes Fe1 . C23 . 2.058(3) yes O1 . C1 . 1.194(3) yes O2 . C1 . 1.354(3) yes O2 . C8 . 1.438(3) yes O3 . C9 . 1.224(3) yes N1 . C2 . 1.481(3) yes N1 . C8 . 1.459(3) yes N1 . C9 . 1.375(3) yes C1 . C2 . 1.529(4) yes C2 . C3 . 1.544(3) yes C2 . C6 . 1.541(4) yes C3 . C4 . 1.497(4) yes C3 . H31 . 0.999 no C3 . H32 . 1.000 no C4 . C5 . 1.322(5) yes C4 . H41 . 1.000 no C5 . H51 . 0.999 no C5 . H52 . 1.000 no C6 . C7 . 1.515(4) yes C6 . H61 . 1.000 no C6 . H62 . 1.000 no C7 . H71 . 1.002 no C7 . H72 . 1.001 no C7 . H73 . 1.000 no C8 . C14 . 1.514(4) yes C8 . H81 . 1.001 no C9 . C10 . 1.537(3) yes C10 . C11 . 1.536(5) yes C10 . C12 . 1.541(4) yes C10 . C13 . 1.529(4) yes C11 . H111 . 0.999 no C11 . H112 . 1.001 no C11 . H113 . 0.998 no C12 . H121 . 0.998 no C12 . H122 . 1.001 no C12 . H123 . 1.001 no C13 . H131 . 0.999 no C13 . H132 . 1.002 no C13 . H133 . 1.001 no C14 . C15 . 1.415(4) yes C14 . C18 . 1.434(3) yes C15 . C16 . 1.432(3) yes C15 . H151 . 0.999 no C16 . C17 . 1.424(4) yes C16 . H161 . 1.000 no C17 . C18 . 1.423(4) yes C17 . H171 . 0.999 no C18 . H181 . 0.997 no C19 . C20 . 1.410(5) yes C19 . C23 . 1.418(5) yes C19 . H191 . 0.998 no C20 . C21 . 1.410(4) yes C20 . H201 . 1.000 no C21 . C22 . 1.423(4) yes C21 . H211 . 1.000 no C22 . C23 . 1.425(4) yes C22 . H221 . 0.998 no C23 . H231 . 0.999 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C14 . Fe1 . C15 . 40.48(12) yes C14 . Fe1 . C16 . 68.6(1) yes C15 . Fe1 . C16 . 41.0(1) yes C14 . Fe1 . C17 . 68.6(1) yes C15 . Fe1 . C17 . 68.6(1) yes C16 . Fe1 . C17 . 40.68(12) yes C14 . Fe1 . C18 . 41.0(1) yes C15 . Fe1 . C18 . 68.59(11) yes C16 . Fe1 . C18 . 68.55(12) yes C17 . Fe1 . C18 . 40.62(11) yes C14 . Fe1 . C19 . 111.93(11) yes C15 . Fe1 . C19 . 127.35(11) yes C16 . Fe1 . C19 . 161.70(13) yes C17 . Fe1 . C19 . 157.57(14) yes C18 . Fe1 . C19 . 124.68(13) yes C14 . Fe1 . C20 . 124.6(1) yes C15 . Fe1 . C20 . 109.08(11) yes C16 . Fe1 . C20 . 123.42(13) yes C17 . Fe1 . C20 . 158.42(12) yes C18 . Fe1 . C20 . 160.27(11) yes C14 . Fe1 . C21 . 157.44(11) yes C15 . Fe1 . C21 . 120.37(12) yes C16 . Fe1 . C21 . 104.42(11) yes C17 . Fe1 . C21 . 120.91(11) yes C18 . Fe1 . C21 . 158.3(1) yes C14 . Fe1 . C22 . 161.68(11) yes C15 . Fe1 . C22 . 154.41(12) yes C16 . Fe1 . C22 . 117.73(11) yes C17 . Fe1 . C22 . 104.3(1) yes C18 . Fe1 . C22 . 122.86(11) yes C14 . Fe1 . C23 . 127.23(12) yes C15 . Fe1 . C23 . 164.00(11) yes C16 . Fe1 . C23 . 154.13(11) yes C17 . Fe1 . C23 . 120.28(12) yes C18 . Fe1 . C23 . 108.64(12) yes C19 . Fe1 . C20 . 40.15(14) yes C19 . Fe1 . C21 . 67.78(12) yes C20 . Fe1 . C21 . 40.32(11) yes C19 . Fe1 . C22 . 67.93(11) yes C20 . Fe1 . C22 . 68.06(11) yes C21 . Fe1 . C22 . 40.74(12) yes C19 . Fe1 . C23 . 40.30(13) yes C20 . Fe1 . C23 . 67.87(13) yes C21 . Fe1 . C23 . 68.25(12) yes C22 . Fe1 . C23 . 40.62(12) yes C1 . O2 . C8 . 110.7(2) yes C2 . N1 . C8 . 110.0(2) yes C2 . N1 . C9 . 122.2(2) yes C8 . N1 . C9 . 127.6(2) yes O1 . C1 . O2 . 121.8(3) yes O1 . C1 . C2 . 127.5(2) yes O2 . C1 . C2 . 110.6(2) yes N1 . C2 . C1 . 99.94(19) yes N1 . C2 . C3 . 114.2(2) yes C1 . C2 . C3 . 108.1(2) yes N1 . C2 . C6 . 111.6(2) yes C1 . C2 . C6 . 110.9(2) yes C3 . C2 . C6 . 111.5(2) yes C2 . C3 . C4 . 114.5(2) yes C2 . C3 . H31 . 108.110 no C4 . C3 . H31 . 108.364 no C2 . C3 . H32 . 107.995 no C4 . C3 . H32 . 108.216 no H31 . C3 . H32 . 109.545 no C3 . C4 . C5 . 123.6(3) yes C3 . C4 . H41 . 118.354 no C5 . C4 . H41 . 118.008 no C4 . C5 . H51 . 120.011 no C4 . C5 . H52 . 119.889 no H51 . C5 . H52 . 120.099 no C2 . C6 . C7 . 115.5(2) yes C2 . C6 . H61 . 107.908 no C7 . C6 . H61 . 108.012 no C2 . C6 . H62 . 107.855 no C7 . C6 . H62 . 107.981 no H61 . C6 . H62 . 109.450 no C6 . C7 . H71 . 109.601 no C6 . C7 . H72 . 109.688 no H71 . C7 . H72 . 109.204 no C6 . C7 . H73 . 109.729 no H71 . C7 . H73 . 109.252 no H72 . C7 . H73 . 109.350 no O2 . C8 . N1 . 103.56(18) yes O2 . C8 . C14 . 111.8(2) yes N1 . C8 . C14 . 115.0(2) yes O2 . C8 . H81 . 111.886 no N1 . C8 . H81 . 109.952 no C14 . C8 . H81 . 104.848 no O3 . C9 . N1 . 118.3(2) yes O3 . C9 . C10 . 120.7(2) yes N1 . C9 . C10 . 120.8(2) yes C9 . C10 . C11 . 109.8(2) yes C9 . C10 . C12 . 107.1(2) yes C11 . C10 . C12 . 106.5(2) yes C9 . C10 . C13 . 114.0(2) yes C11 . C10 . C13 . 110.8(3) yes C12 . C10 . C13 . 108.3(2) yes C10 . C11 . H111 . 109.326 no C10 . C11 . H112 . 109.269 no H111 . C11 . H112 . 109.461 no C10 . C11 . H113 . 109.458 no H111 . C11 . H113 . 109.719 no H112 . C11 . H113 . 109.593 no C10 . C12 . H121 . 109.578 no C10 . C12 . H122 . 109.418 no H121 . C12 . H122 . 109.541 no C10 . C12 . H123 . 109.406 no H121 . C12 . H123 . 109.577 no H122 . C12 . H123 . 109.307 no C10 . C13 . H131 . 109.665 no C10 . C13 . H132 . 109.512 no H131 . C13 . H132 . 109.399 no C10 . C13 . H133 . 109.537 no H131 . C13 . H133 . 109.481 no H132 . C13 . H133 . 109.232 no Fe1 . C14 . C8 . 133.61(18) yes Fe1 . C14 . C15 . 69.52(15) yes C8 . C14 . C15 . 128.3(2) yes Fe1 . C14 . C18 . 69.60(14) yes C8 . C14 . C18 . 123.0(2) yes C15 . C14 . C18 . 108.0(2) yes Fe1 . C15 . C14 . 70.01(15) yes Fe1 . C15 . C16 . 69.73(14) yes C14 . C15 . C16 . 108.3(2) yes Fe1 . C15 . H151 . 126.000 no C14 . C15 . H151 . 125.953 no C16 . C15 . H151 . 125.768 no Fe1 . C16 . C15 . 69.27(15) yes Fe1 . C16 . C17 . 69.68(15) yes C15 . C16 . C17 . 107.6(2) yes Fe1 . C16 . H161 . 126.444 no C15 . C16 . H161 . 126.144 no C17 . C16 . H161 . 126.226 no Fe1 . C17 . C16 . 69.64(14) yes Fe1 . C17 . C18 . 69.76(14) yes C16 . C17 . C18 . 108.4(2) yes Fe1 . C17 . H171 . 126.215 no C16 . C17 . H171 . 125.797 no C18 . C17 . H171 . 125.850 no Fe1 . C18 . C14 . 69.43(14) yes Fe1 . C18 . C17 . 69.61(15) yes C14 . C18 . C17 . 107.7(2) yes Fe1 . C18 . H181 . 126.539 no C14 . C18 . H181 . 126.181 no C17 . C18 . H181 . 126.117 no Fe1 . C19 . C20 . 69.60(16) yes Fe1 . C19 . C23 . 69.83(16) yes C20 . C19 . C23 . 108.4(3) yes Fe1 . C19 . H191 . 126.146 no C20 . C19 . H191 . 126.099 no C23 . C19 . H191 . 125.546 no Fe1 . C20 . C19 . 70.26(17) yes Fe1 . C20 . C21 . 69.49(15) yes C19 . C20 . C21 . 108.3(3) yes Fe1 . C20 . H201 . 126.056 no C19 . C20 . H201 . 125.806 no C21 . C20 . H201 . 125.896 no Fe1 . C21 . C20 . 70.19(15) yes Fe1 . C21 . C22 . 69.86(15) yes C20 . C21 . C22 . 108.1(3) yes Fe1 . C21 . H211 . 125.547 no C20 . C21 . H211 . 126.181 no C22 . C21 . H211 . 125.756 no Fe1 . C22 . C21 . 69.40(15) yes Fe1 . C22 . C23 . 70.11(15) yes C21 . C22 . C23 . 107.7(2) yes Fe1 . C22 . H221 . 126.061 no C21 . C22 . H221 . 126.051 no C23 . C22 . H221 . 126.244 no Fe1 . C23 . C19 . 69.87(17) yes Fe1 . C23 . C22 . 69.27(16) yes C19 . C23 . C22 . 107.6(3) yes Fe1 . C23 . H231 . 126.222 no C19 . C23 . H231 . 126.329 no C22 . C23 . H231 . 126.090 no