# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name _publ_author_address P.E.Kruger ;Department of Chemistry University of Canterbury Private Bag 4800 Christchurch 8140 NEW ZEALAND ; J.R.Thompson ;Department of Chemistry University of Canterbury Private Bag 4800 Christchurch 8140 NEW ZEALAND ; R.J.Archer ;Department of Chemistry University of Canterbury Private Bag 4800 Christchurch 8140 NEW ZEALAND ; C.S.Hawes ;Department of Chemistry University of Canterbury Private Bag 4800 Christchurch 8140 NEW ZEALAND ; A.Ferguson ;Department of Chemistry University of Canterbury Private Bag 4800 Christchurch 8140 NEW ZEALAND ; ; R.Clerac ; ;CNRS, UPR 8641, Centre de Recherche Paul Pascal (CRPP), Equipe Materiaux Moleculaires Magnetiques 115 Avenue du Dr. Albert Schweitzer, F-33600 Pessac, France Universite de Bordeaux, UPR 8641, F-33600 Pessac, France ; C.Mathoniere ;CNRS, Universite de Bordeaux, ICMCB, Groupe des Sciences Moleculaires, 87 Avenue du Dr. Albert Schweitzer, F-33608 Pessac, France; ; A.Wattiaux ;CNRS, Universite de Bordeaux, ICMCB, Groupe des Sciences Moleculaires, 87 Avenue du Dr. Albert Schweitzer, F-33608 Pessac, France; ; _publ_contact_author_address ;Department of Chemistry University of Canterbury Private Bag 4800 Christchurch 8140 NEW ZEALAND ; _publ_contact_author_email paul.kruger@canterbury.ac.nz _publ_contact_author_fax ;+64 3 364 2110 ; _publ_contact_author_phone ;+64 3 364 2438 ; #TrackingRef '- JRT.cif' _publ_contact_author_name 'Paul E. Kruger' data_1_116K _database_code_depnum_ccdc_archive 'CCDC 894553' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H33 Cl2 Fe N9 O11' _chemical_formula_weight 858.43 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.7803(12) _cell_length_b 12.1101(14) _cell_length_c 15.1949(16) _cell_angle_alpha 83.369(7) _cell_angle_beta 85.334(7) _cell_angle_gamma 69.330(7) _cell_volume 1841.8(4) _cell_formula_units_Z 2 _cell_measurement_temperature 116(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.548 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 884 _exptl_absorpt_coefficient_mu 0.628 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7443 _exptl_absorpt_correction_T_max 0.9062 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 116(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 27316 _diffrn_reflns_av_R_equivalents 0.0825 _diffrn_reflns_av_sigmaI/netI 0.0808 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 25.05 _reflns_number_total 6515 _reflns_number_gt 4373 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0420P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6515 _refine_ls_number_parameters 508 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0691 _refine_ls_R_factor_gt 0.0422 _refine_ls_wR_factor_ref 0.0972 _refine_ls_wR_factor_gt 0.0898 _refine_ls_goodness_of_fit_ref 0.897 _refine_ls_restrained_S_all 0.897 _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 Fe1 Fe 0.46785(4) 0.10727(4) 0.22509(3) 0.02089(13) Uani 1 1 d . . . Cl1 Cl 0.29434(9) 0.41347(8) 0.58827(5) 0.0383(2) Uani 1 1 d . . . N7 N 0.5347(2) 0.2310(2) 0.26077(14) 0.0218(6) Uani 1 1 d . . . N6 N 0.2751(2) 0.2250(2) 0.21715(14) 0.0216(6) Uani 1 1 d . . . N4 N 0.3753(2) -0.0011(2) 0.19831(14) 0.0241(6) Uani 1 1 d . . . N3 N 0.5307(2) 0.1335(2) 0.09589(15) 0.0228(6) Uani 1 1 d . . . N9 N 0.4221(2) 0.0969(2) 0.36059(15) 0.0236(6) Uani 1 1 d . . . N1 N 0.6464(3) -0.0198(2) 0.22547(15) 0.0285(6) Uani 1 1 d . . . O1 O 0.2581(2) 0.49392(18) -0.15468(12) 0.0314(5) Uani 1 1 d . . . O3 O 0.1927(2) -0.2047(2) 0.56024(13) 0.0389(6) Uani 1 1 d . . . N8 N 0.5233(3) 0.3511(2) 0.36246(15) 0.0305(7) Uani 1 1 d . . . H8 H 0.5055 0.3829 0.4119 0.037 Uiso 1 1 calc R . . C5 C 0.4616(3) 0.2246(3) 0.02981(17) 0.0229(7) Uani 1 1 d . . . C8 C 0.3197(3) 0.4024(3) -0.09427(18) 0.0251(7) Uani 1 1 d . . . C28 C 0.3970(3) -0.0961(3) 0.39758(18) 0.0267(7) Uani 1 1 d . . . H28 H 0.4620 -0.1268 0.3540 0.032 Uiso 1 1 calc R . . C10 C 0.3374(3) 0.2309(3) 0.00647(18) 0.0269(7) Uani 1 1 d . . . H10 H 0.3011 0.1752 0.0327 0.032 Uiso 1 1 calc R . . C6 C 0.5156(3) 0.3082(3) -0.01021(18) 0.0250(7) Uani 1 1 d . . . H6 H 0.5994 0.3041 0.0042 0.030 Uiso 1 1 calc R . . C25 C 0.4960(3) 0.2559(3) 0.34424(18) 0.0235(7) Uani 1 1 d . . . C9 C 0.2669(3) 0.3190(3) -0.05526(18) 0.0260(7) Uani 1 1 d . . . H9 H 0.1839 0.3222 -0.0706 0.031 Uiso 1 1 calc R . . C16 C 0.2294(3) 0.3458(3) 0.23963(18) 0.0245(7) Uani 1 1 d . . . C27 C 0.3575(3) 0.0244(3) 0.41197(18) 0.0254(7) Uani 1 1 d . . . C15 C 0.1878(3) 0.1765(3) 0.20747(17) 0.0238(7) Uani 1 1 d . . . H15 H 0.0969 0.2180 0.2091 0.029 Uiso 1 1 calc R . . C26 C 0.4376(3) 0.1819(3) 0.39935(18) 0.0266(7) Uani 1 1 d . . . H26 H 0.4124 0.1933 0.4586 0.032 Uiso 1 1 calc R . . O2 O 0.1337(2) 0.6872(2) 0.31020(17) 0.0471(7) Uani 1 1 d . . . N2 N 0.8366(3) -0.1005(2) 0.15113(18) 0.0372(7) Uani 1 1 d . . . H2 H 0.8973 -0.1139 0.1093 0.045 Uiso 1 1 calc R . . C7 C 0.4448(3) 0.3968(3) -0.07107(18) 0.0266(7) Uani 1 1 d . . . H7 H 0.4803 0.4532 -0.0969 0.032 Uiso 1 1 calc R . . C23 C 0.5913(3) 0.3127(3) 0.22565(19) 0.0261(7) Uani 1 1 d . . . H23 H 0.6282 0.3164 0.1684 0.031 Uiso 1 1 calc R . . N5 N 0.1860(3) -0.0240(2) 0.17631(17) 0.0364(7) Uani 1 1 d . . . H5 H 0.1026 -0.0087 0.1709 0.044 Uiso 1 1 calc R . . C19 C 0.1601(3) 0.5731(3) 0.2901(2) 0.0339(8) Uani 1 1 d . . . C14 C 0.2444(3) 0.0527(3) 0.19407(18) 0.0257(7) Uani 1 1 d . . . C13 C 0.2858(4) -0.1310(3) 0.1685(2) 0.0393(9) Uani 1 1 d . . . H13 H 0.2759 -0.2008 0.1562 0.047 Uiso 1 1 calc R . . C3 C 0.7155(3) -0.0166(3) 0.14830(19) 0.0271(7) Uani 1 1 d . . . C18 C 0.1247(3) 0.4889(3) 0.3453(2) 0.0351(8) Uani 1 1 d . . . H18 H 0.0791 0.5079 0.3992 0.042 Uiso 1 1 calc R . . C29 C 0.3394(3) -0.1688(3) 0.44801(19) 0.0289(8) Uani 1 1 d . . . H29 H 0.3661 -0.2484 0.4383 0.035 Uiso 1 1 calc R . . C17 C 0.1585(3) 0.3754(3) 0.3189(2) 0.0326(8) Uani 1 1 d . . . H17 H 0.1332 0.3188 0.3548 0.039 Uiso 1 1 calc R . . C4 C 0.6516(3) 0.0688(3) 0.07735(19) 0.0263(7) Uani 1 1 d . . . H4 H 0.6940 0.0767 0.0225 0.032 Uiso 1 1 calc R . . C30 C 0.2421(3) -0.1245(3) 0.51308(19) 0.0298(8) Uani 1 1 d . . . C32 C 0.2577(3) 0.0684(3) 0.47514(19) 0.0307(8) Uani 1 1 d . . . H32 H 0.2285 0.1487 0.4834 0.037 Uiso 1 1 calc R . . C24 C 0.5847(3) 0.3881(3) 0.28834(19) 0.0294(8) Uani 1 1 d . . . H24 H 0.6155 0.4514 0.2818 0.035 Uiso 1 1 calc R . . C31 C 0.1998(3) -0.0049(3) 0.5268(2) 0.0324(8) Uani 1 1 d . . . H31 H 0.1339 0.0257 0.5698 0.039 Uiso 1 1 calc R . . C12 C 0.4016(4) -0.1162(3) 0.18212(19) 0.0325(8) Uani 1 1 d . . . H12 H 0.4852 -0.1748 0.1807 0.039 Uiso 1 1 calc R . . C21 C 0.2619(3) 0.4318(3) 0.1836(2) 0.0357(8) Uani 1 1 d . . . H21 H 0.3081 0.4129 0.1298 0.043 Uiso 1 1 calc R . . C2 C 0.8445(4) -0.1605(3) 0.2338(2) 0.0465(10) Uani 1 1 d . . . H2A H 0.9167 -0.2241 0.2552 0.056 Uiso 1 1 calc R . . C1 C 0.7279(4) -0.1103(3) 0.2787(2) 0.0401(9) Uani 1 1 d . . . H1 H 0.7067 -0.1339 0.3367 0.048 Uiso 1 1 calc R . . C20 C 0.2248(3) 0.5450(3) 0.2087(2) 0.0428(9) Uani 1 1 d . . . H20 H 0.2435 0.6035 0.1705 0.051 Uiso 1 1 calc R . . C33 C 0.1063(4) -0.1690(3) 0.6355(2) 0.0502(10) Uani 1 1 d . . . H33A H 0.0256 -0.1081 0.6168 0.075 Uiso 1 1 calc R . . H33C H 0.1485 -0.1391 0.6756 0.075 Uiso 1 1 calc R . . H33B H 0.0866 -0.2358 0.6648 0.075 Uiso 1 1 calc R . . C11 C 0.1263(3) 0.5089(3) -0.1753(2) 0.0419(9) Uani 1 1 d . . . H11C H 0.0936 0.5770 -0.2173 0.063 Uiso 1 1 calc R . . H11B H 0.0704 0.5202 -0.1222 0.063 Uiso 1 1 calc R . . H11A H 0.1262 0.4397 -0.2002 0.063 Uiso 1 1 calc R . . C22 C 0.0844(4) 0.7136(3) 0.3986(2) 0.0605(12) Uani 1 1 d . . . H22C H 0.0779 0.7930 0.4066 0.091 Uiso 1 1 calc R . . H22B H 0.1439 0.6589 0.4404 0.091 Uiso 1 1 calc R . . H22A H -0.0018 0.7066 0.4082 0.091 Uiso 1 1 calc R . . Cl2 Cl 0.92550(8) 0.19525(8) 0.03891(6) 0.0403(2) Uani 1 1 d . . . O6 O 0.3591(3) 0.3587(2) 0.66894(15) 0.0530(7) Uani 1 1 d . . . O11 O 1.0521(2) 0.2074(3) 0.02906(15) 0.0597(8) Uani 1 1 d . . . O9 O 0.9164(2) 0.1273(2) 0.12194(17) 0.0571(7) Uani 1 1 d . . . O7 O 0.1841(2) 0.5179(2) 0.60509(16) 0.0531(7) Uani 1 1 d . . . O8 O 0.8220(3) 0.3065(2) 0.03680(17) 0.0675(8) Uani 1 1 d . . . O5 O 0.2502(3) 0.3298(2) 0.55111(16) 0.0620(8) Uani 1 1 d . . . O4 O 0.3873(3) 0.4457(2) 0.52632(17) 0.0659(8) Uani 1 1 d . . . O10 O 0.9114(3) 0.1334(3) -0.03355(19) 0.0807(10) 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 Fe1 0.0264(3) 0.0221(3) 0.0184(2) -0.00380(18) -0.00041(17) -0.0133(2) Cl1 0.0536(6) 0.0348(5) 0.0323(5) -0.0110(4) 0.0072(4) -0.0221(5) N7 0.0278(15) 0.0222(15) 0.0186(13) -0.0031(10) 0.0002(10) -0.0124(12) N6 0.0301(15) 0.0183(14) 0.0176(12) -0.0009(10) 0.0006(10) -0.0104(12) N4 0.0300(16) 0.0228(15) 0.0190(13) -0.0030(11) -0.0015(11) -0.0082(12) N3 0.0256(15) 0.0192(15) 0.0280(14) -0.0025(11) -0.0039(11) -0.0124(12) N9 0.0246(15) 0.0223(15) 0.0260(13) 0.0009(11) -0.0005(11) -0.0119(12) N1 0.0371(17) 0.0336(17) 0.0242(14) 0.0056(12) -0.0066(12) -0.0254(14) O1 0.0356(14) 0.0266(13) 0.0291(12) 0.0054(10) -0.0071(10) -0.0083(11) O3 0.0514(16) 0.0410(15) 0.0336(13) 0.0001(11) 0.0046(11) -0.0301(13) N8 0.0446(18) 0.0321(17) 0.0253(14) -0.0088(12) -0.0011(12) -0.0244(14) C5 0.0291(19) 0.0234(18) 0.0195(15) -0.0024(13) -0.0029(13) -0.0125(15) C8 0.0303(19) 0.0234(18) 0.0196(15) -0.0034(13) -0.0002(13) -0.0065(15) C28 0.0333(19) 0.0275(19) 0.0218(16) -0.0009(14) -0.0011(13) -0.0142(16) C10 0.0331(19) 0.0280(19) 0.0247(16) -0.0027(14) -0.0015(14) -0.0170(16) C6 0.0275(18) 0.0252(19) 0.0252(16) -0.0075(14) -0.0009(13) -0.0112(15) C25 0.0291(18) 0.0253(19) 0.0202(16) -0.0043(13) -0.0039(13) -0.0130(15) C9 0.0296(19) 0.0297(19) 0.0235(16) -0.0022(14) -0.0043(13) -0.0157(15) C16 0.0239(18) 0.0236(18) 0.0267(16) -0.0043(14) -0.0047(13) -0.0077(14) C27 0.0277(19) 0.0278(19) 0.0245(16) 0.0001(14) -0.0030(13) -0.0147(15) C15 0.0242(18) 0.0279(19) 0.0227(16) -0.0069(13) 0.0022(13) -0.0126(15) C26 0.034(2) 0.033(2) 0.0169(15) -0.0033(14) -0.0024(13) -0.0159(16) O2 0.0426(16) 0.0261(14) 0.0749(18) -0.0245(13) -0.0070(13) -0.0077(12) N2 0.0306(17) 0.0323(18) 0.0446(17) -0.0092(14) -0.0038(13) -0.0036(14) C7 0.037(2) 0.0224(18) 0.0249(16) -0.0014(14) 0.0007(14) -0.0164(15) C23 0.0305(19) 0.0272(19) 0.0249(16) 0.0009(14) 0.0021(13) -0.0167(15) N5 0.0385(18) 0.0347(18) 0.0468(17) -0.0122(14) -0.0020(13) -0.0234(15) C19 0.029(2) 0.0204(19) 0.053(2) -0.0131(16) -0.0110(16) -0.0055(15) C14 0.035(2) 0.0241(19) 0.0233(16) -0.0059(13) -0.0001(14) -0.0157(16) C13 0.061(3) 0.024(2) 0.038(2) -0.0102(16) -0.0023(17) -0.0192(19) C3 0.0297(19) 0.0246(19) 0.0323(18) -0.0016(14) -0.0068(14) -0.0149(16) C18 0.036(2) 0.036(2) 0.0323(18) -0.0155(16) -0.0005(15) -0.0070(17) C29 0.040(2) 0.0243(19) 0.0270(17) -0.0014(14) -0.0069(15) -0.0160(16) C17 0.038(2) 0.030(2) 0.0313(18) -0.0058(15) 0.0007(15) -0.0142(17) C4 0.033(2) 0.0253(19) 0.0255(16) -0.0049(14) 0.0002(14) -0.0160(16) C30 0.036(2) 0.034(2) 0.0274(17) 0.0039(15) -0.0067(15) -0.0230(17) C32 0.037(2) 0.029(2) 0.0312(18) -0.0032(15) -0.0025(15) -0.0174(16) C24 0.039(2) 0.029(2) 0.0307(17) -0.0014(14) -0.0052(14) -0.0245(16) C31 0.031(2) 0.034(2) 0.0340(18) -0.0045(15) 0.0043(14) -0.0143(16) C12 0.044(2) 0.023(2) 0.0287(17) -0.0088(14) -0.0016(15) -0.0077(17) C21 0.039(2) 0.028(2) 0.0393(19) -0.0034(16) 0.0100(15) -0.0123(17) C2 0.062(3) 0.028(2) 0.050(2) 0.0095(18) -0.031(2) -0.014(2) C1 0.045(2) 0.039(2) 0.040(2) 0.0104(17) -0.0148(18) -0.0214(19) C20 0.044(2) 0.024(2) 0.060(2) -0.0067(18) 0.0109(18) -0.0122(18) C33 0.048(2) 0.058(3) 0.046(2) 0.0094(19) 0.0066(18) -0.027(2) C11 0.038(2) 0.044(2) 0.038(2) 0.0071(17) -0.0119(16) -0.0098(18) C22 0.067(3) 0.037(2) 0.069(3) -0.033(2) -0.023(2) 0.005(2) Cl2 0.0307(5) 0.0500(6) 0.0488(5) -0.0228(4) 0.0011(4) -0.0196(4) O6 0.077(2) 0.0452(17) 0.0420(15) -0.0067(12) -0.0117(13) -0.0247(15) O11 0.0369(16) 0.103(2) 0.0537(16) 0.0063(15) -0.0062(12) -0.0458(16) O9 0.0483(17) 0.067(2) 0.0617(17) -0.0062(14) 0.0138(13) -0.0309(15) O7 0.0530(17) 0.0358(16) 0.0676(17) -0.0139(13) 0.0130(13) -0.0125(13) O8 0.0585(19) 0.058(2) 0.0724(19) -0.0241(15) -0.0006(15) 0.0013(16) O5 0.100(2) 0.0524(18) 0.0513(16) -0.0201(13) -0.0117(14) -0.0413(17) O4 0.078(2) 0.068(2) 0.0559(17) -0.0176(14) 0.0338(14) -0.0342(17) O10 0.075(2) 0.104(3) 0.088(2) -0.0721(19) 0.0098(16) -0.0456(19) _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 Fe1 N1 1.996(3) . ? Fe1 N4 2.000(3) . ? Fe1 N7 2.018(2) . ? Fe1 N3 2.051(2) . ? Fe1 N6 2.067(2) . ? Fe1 N9 2.078(2) . ? Cl1 O7 1.429(2) . ? Cl1 O6 1.433(2) . ? Cl1 O4 1.442(3) . ? Cl1 O5 1.445(2) . ? N7 C25 1.337(3) . ? N7 C23 1.373(3) . ? N6 C15 1.299(4) . ? N6 C16 1.442(4) . ? N4 C14 1.332(4) . ? N4 C12 1.368(4) . ? N3 C4 1.290(4) . ? N3 C5 1.437(3) . ? N9 C26 1.308(4) . ? N9 C27 1.432(4) . ? N1 C3 1.341(4) . ? N1 C1 1.364(4) . ? O1 C8 1.363(3) . ? O1 C11 1.423(4) . ? O3 C30 1.372(3) . ? O3 C33 1.420(4) . ? N8 C25 1.349(4) . ? N8 C24 1.371(4) . ? N8 H8 0.8600 . ? C5 C10 1.387(4) . ? C5 C6 1.397(4) . ? C8 C9 1.381(4) . ? C8 C7 1.398(4) . ? C28 C29 1.378(4) . ? C28 C27 1.407(4) . ? C28 H28 0.9300 . ? C10 C9 1.382(4) . ? C10 H10 0.9300 . ? C6 C7 1.377(4) . ? C6 H6 0.9300 . ? C25 C26 1.429(4) . ? C9 H9 0.9300 . ? C16 C17 1.385(4) . ? C16 C21 1.391(4) . ? C27 C32 1.381(4) . ? C15 C14 1.437(4) . ? C15 H15 0.9300 . ? C26 H26 0.9300 . ? O2 C19 1.375(4) . ? O2 C22 1.433(4) . ? N2 C3 1.342(4) . ? N2 C2 1.370(4) . ? N2 H2 0.8600 . ? C7 H7 0.9300 . ? C23 C24 1.375(4) . ? C23 H23 0.9300 . ? N5 C14 1.353(4) . ? N5 C13 1.371(4) . ? N5 H5 0.8600 . ? C19 C18 1.382(4) . ? C19 C20 1.387(5) . ? C13 C12 1.357(4) . ? C13 H13 0.9300 . ? C3 C4 1.438(4) . ? C18 C17 1.391(4) . ? C18 H18 0.9300 . ? C29 C30 1.387(4) . ? C29 H29 0.9300 . ? C17 H17 0.9300 . ? C4 H4 0.9300 . ? C30 C31 1.391(4) . ? C32 C31 1.394(4) . ? C32 H32 0.9300 . ? C24 H24 0.9300 . ? C31 H31 0.9300 . ? C12 H12 0.9300 . ? C21 C20 1.377(4) . ? C21 H21 0.9300 . ? C2 C1 1.354(5) . ? C2 H2A 0.9300 . ? C1 H1 0.9300 . ? C20 H20 0.9300 . ? C33 H33A 0.9600 . ? C33 H33C 0.9600 . ? C33 H33B 0.9600 . ? C11 H11C 0.9600 . ? C11 H11B 0.9600 . ? C11 H11A 0.9600 . ? C22 H22C 0.9600 . ? C22 H22B 0.9600 . ? C22 H22A 0.9600 . ? Cl2 O8 1.413(3) . ? Cl2 O11 1.418(2) . ? Cl2 O9 1.441(2) . ? Cl2 O10 1.447(3) . ? 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 N1 Fe1 N4 93.55(10) . . ? N1 Fe1 N7 94.25(10) . . ? N4 Fe1 N7 171.30(10) . . ? N1 Fe1 N3 80.25(10) . . ? N4 Fe1 N3 94.21(9) . . ? N7 Fe1 N3 90.91(9) . . ? N1 Fe1 N6 172.97(10) . . ? N4 Fe1 N6 79.66(10) . . ? N7 Fe1 N6 92.66(10) . . ? N3 Fe1 N6 98.29(9) . . ? N1 Fe1 N9 98.40(9) . . ? N4 Fe1 N9 95.03(9) . . ? N7 Fe1 N9 80.02(9) . . ? N3 Fe1 N9 170.73(10) . . ? N6 Fe1 N9 84.13(9) . . ? O7 Cl1 O6 110.28(15) . . ? O7 Cl1 O4 108.91(16) . . ? O6 Cl1 O4 109.13(17) . . ? O7 Cl1 O5 110.32(17) . . ? O6 Cl1 O5 108.87(15) . . ? O4 Cl1 O5 109.32(16) . . ? C25 N7 C23 106.0(2) . . ? C25 N7 Fe1 111.50(18) . . ? C23 N7 Fe1 141.59(19) . . ? C15 N6 C16 118.7(3) . . ? C15 N6 Fe1 114.5(2) . . ? C16 N6 Fe1 125.49(19) . . ? C14 N4 C12 106.4(3) . . ? C14 N4 Fe1 112.8(2) . . ? C12 N4 Fe1 140.7(2) . . ? C4 N3 C5 118.1(2) . . ? C4 N3 Fe1 114.31(19) . . ? C5 N3 Fe1 127.03(19) . . ? C26 N9 C27 117.2(2) . . ? C26 N9 Fe1 112.83(19) . . ? C27 N9 Fe1 129.1(2) . . ? C3 N1 C1 105.8(3) . . ? C3 N1 Fe1 112.27(19) . . ? C1 N1 Fe1 141.9(2) . . ? C8 O1 C11 117.6(2) . . ? C30 O3 C33 118.8(3) . . ? C25 N8 C24 107.9(2) . . ? C25 N8 H8 126.1 . . ? C24 N8 H8 126.1 . . ? C10 C5 C6 119.3(3) . . ? C10 C5 N3 119.2(3) . . ? C6 C5 N3 121.5(3) . . ? O1 C8 C9 124.9(3) . . ? O1 C8 C7 115.4(3) . . ? C9 C8 C7 119.6(3) . . ? C29 C28 C27 120.0(3) . . ? C29 C28 H28 120.0 . . ? C27 C28 H28 120.0 . . ? C9 C10 C5 120.7(3) . . ? C9 C10 H10 119.7 . . ? C5 C10 H10 119.7 . . ? C7 C6 C5 120.0(3) . . ? C7 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? N7 C25 N8 110.7(2) . . ? N7 C25 C26 119.0(3) . . ? N8 C25 C26 130.4(3) . . ? C8 C9 C10 120.1(3) . . ? C8 C9 H9 120.0 . . ? C10 C9 H9 120.0 . . ? C17 C16 C21 119.9(3) . . ? C17 C16 N6 120.2(3) . . ? C21 C16 N6 119.9(3) . . ? C32 C27 C28 118.8(3) . . ? C32 C27 N9 122.4(3) . . ? C28 C27 N9 118.8(3) . . ? N6 C15 C14 113.8(3) . . ? N6 C15 H15 123.1 . . ? C14 C15 H15 123.1 . . ? N9 C26 C25 115.2(3) . . ? N9 C26 H26 122.4 . . ? C25 C26 H26 122.4 . . ? C19 O2 C22 116.9(3) . . ? C3 N2 C2 106.5(3) . . ? C3 N2 H2 126.8 . . ? C2 N2 H2 126.8 . . ? C6 C7 C8 120.3(3) . . ? C6 C7 H7 119.9 . . ? C8 C7 H7 119.9 . . ? N7 C23 C24 109.4(3) . . ? N7 C23 H23 125.3 . . ? C24 C23 H23 125.3 . . ? C14 N5 C13 106.6(3) . . ? C14 N5 H5 126.7 . . ? C13 N5 H5 126.7 . . ? O2 C19 C18 123.9(3) . . ? O2 C19 C20 115.9(3) . . ? C18 C19 C20 120.2(3) . . ? N4 C14 N5 110.7(3) . . ? N4 C14 C15 118.8(3) . . ? N5 C14 C15 130.4(3) . . ? C12 C13 N5 107.4(3) . . ? C12 C13 H13 126.3 . . ? N5 C13 H13 126.3 . . ? N1 C3 N2 111.1(3) . . ? N1 C3 C4 118.1(3) . . ? N2 C3 C4 130.7(3) . . ? C19 C18 C17 119.0(3) . . ? C19 C18 H18 120.5 . . ? C17 C18 H18 120.5 . . ? C28 C29 C30 120.8(3) . . ? C28 C29 H29 119.6 . . ? C30 C29 H29 119.6 . . ? C16 C17 C18 120.7(3) . . ? C16 C17 H17 119.6 . . ? C18 C17 H17 119.6 . . ? N3 C4 C3 114.7(3) . . ? N3 C4 H4 122.7 . . ? C3 C4 H4 122.7 . . ? O3 C30 C29 116.0(3) . . ? O3 C30 C31 124.1(3) . . ? C29 C30 C31 119.9(3) . . ? C27 C32 C31 121.4(3) . . ? C27 C32 H32 119.3 . . ? C31 C32 H32 119.3 . . ? N8 C24 C23 106.0(3) . . ? N8 C24 H24 127.0 . . ? C23 C24 H24 127.0 . . ? C30 C31 C32 119.1(3) . . ? C30 C31 H31 120.4 . . ? C32 C31 H31 120.4 . . ? C13 C12 N4 108.9(3) . . ? C13 C12 H12 125.6 . . ? N4 C12 H12 125.6 . . ? C20 C21 C16 119.2(3) . . ? C20 C21 H21 120.4 . . ? C16 C21 H21 120.4 . . ? C1 C2 N2 107.5(3) . . ? C1 C2 H2A 126.3 . . ? N2 C2 H2A 126.3 . . ? C2 C1 N1 109.1(3) . . ? C2 C1 H1 125.4 . . ? N1 C1 H1 125.4 . . ? C21 C20 C19 120.9(3) . . ? C21 C20 H20 119.5 . . ? C19 C20 H20 119.5 . . ? O3 C33 H33A 109.5 . . ? O3 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? O3 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? H33C C33 H33B 109.5 . . ? O1 C11 H11C 109.5 . . ? O1 C11 H11B 109.5 . . ? H11C C11 H11B 109.5 . . ? O1 C11 H11A 109.5 . . ? H11C C11 H11A 109.5 . . ? H11B C11 H11A 109.5 . . ? O2 C22 H22C 109.5 . . ? O2 C22 H22B 109.5 . . ? H22C C22 H22B 109.5 . . ? O2 C22 H22A 109.5 . . ? H22C C22 H22A 109.5 . . ? H22B C22 H22A 109.5 . . ? O8 Cl2 O11 111.81(19) . . ? O8 Cl2 O9 109.43(16) . . ? O11 Cl2 O9 109.10(15) . . ? O8 Cl2 O10 108.51(18) . . ? O11 Cl2 O10 108.39(17) . . ? O9 Cl2 O10 109.57(19) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.439 _refine_diff_density_min -0.459 _refine_diff_density_rms 0.066 ####END data_1_292K _database_code_depnum_ccdc_archive 'CCDC 894554' #TrackingRef '- JRT.cif' _audit_creation_method ; Olex2 1.1-beta (compiled 2010.10.26 svn.r1482, GUI svn.r3310) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C33 H33 Fe N9 O3, 2(Cl O4)' _chemical_formula_sum 'C33 H33 Cl2 Fe N9 O11' _chemical_formula_weight 858.43 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 10.8735(3) _cell_length_b 12.2430(3) _cell_length_c 15.4068(4) _cell_angle_alpha 83.2890(10) _cell_angle_beta 86.1750(10) _cell_angle_gamma 70.1180(10) _cell_volume 1914.75(9) _cell_formula_units_Z 2 _cell_measurement_reflns_used 9768 _cell_measurement_temperature 292(2) _cell_measurement_theta_max 23.89 _cell_measurement_theta_min 2.33 _exptl_absorpt_coefficient_mu 0.604 _exptl_absorpt_correction_T_max 0.8637 _exptl_absorpt_correction_T_min 0.8165 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details SADABS _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.489 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 884 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.25 _exptl_special_details ? _diffrn_reflns_av_R_equivalents 0.0953 _diffrn_reflns_av_unetI/netI 0.0538 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 35225 _diffrn_reflns_theta_full 25.05 _diffrn_reflns_theta_max 25.05 _diffrn_reflns_theta_min 2.33 _diffrn_ambient_temperature 292.0 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source_current 30.0 _diffrn_source_power 1.35 _diffrn_source_voltage 45.0 _diffrn_standards_number 0 _reflns_number_gt 5105 _reflns_number_total 6771 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ? _computing_data_collection ? _computing_data_reduction 'SAINT v7.53A (Bruker, 2008)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution '(Sheldrick, 2007)/Bruker' _refine_diff_density_max 0.374 _refine_diff_density_min -0.432 _refine_diff_density_rms 0.079 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.977 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 508 _refine_ls_number_reflns 6771 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0621 _refine_ls_R_factor_gt 0.0471 _refine_ls_restrained_S_all 0.977 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0850P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1259 _refine_ls_wR_factor_ref 0.1338 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.47588(4) 0.09822(3) 0.22603(2) 0.03425(14) Uani 1 1 d . . . Cl1 Cl 0.29914(10) 0.41090(8) 0.58557(5) 0.0665(3) Uani 1 1 d . . . N6 N 0.5381(2) 0.13173(19) 0.08741(13) 0.0375(5) Uani 1 1 d . . . N3 N 0.4251(2) 0.09720(19) 0.37005(13) 0.0375(5) Uani 1 1 d . . . N9 N 0.2670(2) 0.22274(18) 0.21818(13) 0.0378(5) Uani 1 1 d . . . N1 N 0.5411(2) 0.23057(18) 0.26404(13) 0.0376(5) Uani 1 1 d . . . N4 N 0.6624(2) -0.03552(19) 0.21582(14) 0.0412(5) Uani 1 1 d . . . N7 N 0.3653(2) -0.00854(19) 0.20065(13) 0.0405(5) Uani 1 1 d . . . N2 N 0.5181(2) 0.3539(2) 0.36155(15) 0.0493(6) Uani 1 1 d . . . H2 H 0.4970 0.3865 0.4094 0.059 Uiso 1 1 calc R . . C17 C 0.5224(3) 0.3062(2) -0.01495(17) 0.0429(7) Uani 1 1 d . . . H17 H 0.6062 0.3016 -0.0015 0.052 Uiso 1 1 calc R . . C5 C 0.3596(3) 0.0277(2) 0.42117(16) 0.0398(6) Uani 1 1 d . . . C27 C 0.2219(3) 0.3402(2) 0.24014(18) 0.0410(6) Uani 1 1 d . . . C16 C 0.4695(3) 0.2235(2) 0.02404(15) 0.0369(6) Uani 1 1 d . . . O2 O 0.2638(2) 0.49296(17) -0.15339(13) 0.0568(6) Uani 1 1 d . . . C4 C 0.4364(3) 0.1862(3) 0.40082(17) 0.0428(7) Uani 1 1 d . . . H4 H 0.4070 0.2041 0.4572 0.051 Uiso 1 1 calc R . . C3 C 0.4969(3) 0.2576(2) 0.34413(16) 0.0383(6) Uani 1 1 d . . . C19 C 0.3258(3) 0.4023(2) -0.09515(16) 0.0427(7) Uani 1 1 d . . . C21 C 0.3446(3) 0.2318(2) 0.00384(16) 0.0427(7) Uani 1 1 d . . . H21 H 0.3086 0.1772 0.0308 0.051 Uiso 1 1 calc R . . C25 C 0.2387(3) 0.0482(3) 0.19826(17) 0.0441(7) Uani 1 1 d . . . C26 C 0.1853(3) 0.1701(3) 0.21186(17) 0.0448(7) Uani 1 1 d . . . H26 H 0.0955 0.2086 0.2158 0.054 Uiso 1 1 calc R . . C14 C 0.7212(3) -0.0194(2) 0.13968(17) 0.0420(6) Uani 1 1 d . . . C15 C 0.6562(3) 0.0704(2) 0.07206(17) 0.0428(7) Uani 1 1 d . . . H15 H 0.6991 0.0826 0.0195 0.051 Uiso 1 1 calc R . . N5 N 0.8427(2) -0.0965(2) 0.13638(17) 0.0574(7) Uani 1 1 d . . . H5 H 0.8982 -0.1009 0.0933 0.069 Uiso 1 1 calc R . . C20 C 0.2723(3) 0.3197(3) -0.05559(17) 0.0470(7) Uani 1 1 d . . . H20 H 0.1887 0.3238 -0.0691 0.056 Uiso 1 1 calc R . . C6 C 0.3937(3) -0.0887(3) 0.40677(17) 0.0467(7) Uani 1 1 d . . . H6 H 0.4581 -0.1191 0.3648 0.056 Uiso 1 1 calc R . . C1 C 0.5931(3) 0.3148(2) 0.23099(18) 0.0438(7) Uani 1 1 d . . . H1 H 0.6324 0.3187 0.1758 0.053 Uiso 1 1 calc R . . C18 C 0.4505(3) 0.3949(2) -0.07352(18) 0.0472(7) Uani 1 1 d . . . H18 H 0.4859 0.4507 -0.0990 0.057 Uiso 1 1 calc R . . O3 O 0.1329(2) 0.67540(19) 0.30760(19) 0.0788(7) Uani 1 1 d . . . C2 C 0.5788(3) 0.3913(3) 0.29032(19) 0.0517(8) Uani 1 1 d . . . H2A H 0.6053 0.4565 0.2837 0.062 Uiso 1 1 calc R . . C32 C 0.1514(3) 0.3697(3) 0.31660(19) 0.0516(7) Uani 1 1 d . . . H32 H 0.1245 0.3144 0.3517 0.062 Uiso 1 1 calc R . . C13 C 0.7516(3) -0.1271(3) 0.2618(2) 0.0552(8) Uani 1 1 d . . . H13 H 0.7381 -0.1581 0.3182 0.066 Uiso 1 1 calc R . . O1 O 0.1876(3) -0.1964(2) 0.56047(16) 0.0847(8) Uani 1 1 d . . . C10 C 0.2631(3) 0.0710(3) 0.48425(19) 0.0529(8) Uani 1 1 d . . . H10 H 0.2386 0.1490 0.4946 0.064 Uiso 1 1 calc R . . C24 C 0.3822(4) -0.1212(3) 0.18727(19) 0.0552(8) Uani 1 1 d . . . H24 H 0.4620 -0.1815 0.1855 0.066 Uiso 1 1 calc R . . N8 N 0.1739(3) -0.0232(2) 0.18353(19) 0.0675(8) Uani 1 1 d . . . H8 H 0.0906 -0.0044 0.1791 0.081 Uiso 1 1 calc R . . C28 C 0.2585(3) 0.4240(3) 0.1869(2) 0.0575(8) Uani 1 1 d . . . H28 H 0.3062 0.4051 0.1351 0.069 Uiso 1 1 calc R . . C12 C 0.8628(3) -0.1658(3) 0.2124(2) 0.0665(9) Uani 1 1 d . . . H12 H 0.9380 -0.2280 0.2279 0.080 Uiso 1 1 calc R . . C31 C 0.1204(3) 0.4809(3) 0.3416(2) 0.0592(8) Uani 1 1 d . . . H31 H 0.0742 0.4997 0.3939 0.071 Uiso 1 1 calc R . . C30 C 0.1575(3) 0.5635(3) 0.2895(2) 0.0560(8) Uani 1 1 d . . . C9 C 0.2033(3) -0.0012(3) 0.5318(2) 0.0598(9) Uani 1 1 d . . . H9 H 0.1388 0.0283 0.5739 0.072 Uiso 1 1 calc R . . C7 C 0.3332(3) -0.1602(3) 0.45395(19) 0.0540(8) Uani 1 1 d . . . H7 H 0.3561 -0.2379 0.4431 0.065 Uiso 1 1 calc R . . O5 O 0.2503(4) 0.3303(3) 0.5536(2) 0.1209(12) Uani 1 1 d . . . C8 C 0.2395(3) -0.1171(3) 0.51666(19) 0.0572(9) Uani 1 1 d . . . O7 O 0.1989(3) 0.5124(3) 0.6060(2) 0.1080(10) Uani 1 1 d . . . C23 C 0.2640(4) -0.1307(3) 0.1770(2) 0.0712(10) Uani 1 1 d . . . H23 H 0.2475 -0.1979 0.1672 0.085 Uiso 1 1 calc R . . O6 O 0.3657(4) 0.3572(3) 0.6637(2) 0.1230(12) Uani 1 1 d . . . C29 C 0.2238(4) 0.5347(3) 0.2110(2) 0.0683(10) Uani 1 1 d . . . H29 H 0.2452 0.5916 0.1741 0.082 Uiso 1 1 calc R . . C22 C 0.1333(4) 0.5075(3) -0.1739(2) 0.0751(11) Uani 1 1 d . . . H22C H 0.0991 0.5774 -0.2127 0.113 Uiso 1 1 calc R . . H22B H 0.0802 0.5133 -0.1212 0.113 Uiso 1 1 calc R . . H22A H 0.1326 0.4416 -0.2018 0.113 Uiso 1 1 calc R . . C33 C 0.0839(5) 0.7033(4) 0.3941(3) 0.1103(17) Uani 1 1 d . . . H33C H 0.0806 0.7811 0.4013 0.165 Uiso 1 1 calc R . . H33B H 0.1407 0.6491 0.4364 0.165 Uiso 1 1 calc R . . H33A H -0.0024 0.6983 0.4024 0.165 Uiso 1 1 calc R . . Cl2 Cl 0.92605(8) 0.20170(9) 0.04223(6) 0.0671(3) Uani 1 1 d . . . O9 O 0.9102(3) 0.1409(3) 0.1265(2) 0.1133(11) Uani 1 1 d . . . O11 O 1.0493(3) 0.2118(3) 0.03629(17) 0.1060(11) Uani 1 1 d . . . O10 O 0.8249(4) 0.3061(3) 0.0347(3) 0.1448(15) Uani 1 1 d . . . O8 O 0.9160(3) 0.1352(4) -0.0246(2) 0.1383(16) Uani 1 1 d . . . O4 O 0.3877(4) 0.4404(3) 0.5242(2) 0.1334(14) Uani 1 1 d . . . C11 C 0.1049(4) -0.1635(4) 0.6330(3) 0.1035(16) Uani 1 1 d . . . H11A H 0.0270 -0.1011 0.6148 0.155 Uiso 1 1 calc R . . H11C H 0.1488 -0.1378 0.6743 0.155 Uiso 1 1 calc R . . H11B H 0.0820 -0.2291 0.6598 0.155 Uiso 1 1 calc R . . 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 0.0355(2) 0.0359(2) 0.0317(2) -0.00470(15) 0.00427(16) -0.01296(17) Cl1 0.0869(7) 0.0642(5) 0.0570(5) -0.0228(4) 0.0201(5) -0.0350(5) N6 0.0399(14) 0.0419(13) 0.0318(11) -0.0037(9) 0.0016(10) -0.0158(11) N3 0.0405(13) 0.0421(13) 0.0305(11) 0.0007(9) 0.0010(9) -0.0162(10) N9 0.0378(13) 0.0383(12) 0.0374(12) -0.0065(9) 0.0022(10) -0.0125(10) N1 0.0376(13) 0.0437(13) 0.0334(11) -0.0030(9) 0.0021(9) -0.0169(10) N4 0.0412(14) 0.0411(13) 0.0368(12) -0.0015(10) -0.0001(10) -0.0091(10) N7 0.0522(16) 0.0390(13) 0.0334(11) -0.0073(9) 0.0030(10) -0.0189(11) N2 0.0619(17) 0.0557(15) 0.0394(13) -0.0137(11) 0.0031(12) -0.0294(13) C17 0.0357(16) 0.0511(17) 0.0449(15) -0.0024(13) 0.0016(12) -0.0196(13) C5 0.0427(16) 0.0502(17) 0.0289(13) -0.0007(11) 0.0013(12) -0.0202(13) C27 0.0333(15) 0.0384(15) 0.0492(16) -0.0061(12) -0.0058(12) -0.0081(12) C16 0.0409(16) 0.0418(15) 0.0278(12) -0.0037(11) 0.0032(11) -0.0143(12) O2 0.0544(14) 0.0546(13) 0.0527(12) 0.0124(10) -0.0082(10) -0.0118(10) C4 0.0443(17) 0.0584(18) 0.0293(13) -0.0057(12) 0.0035(12) -0.0223(14) C3 0.0411(16) 0.0441(16) 0.0334(13) -0.0050(11) -0.0009(12) -0.0188(13) C19 0.0463(17) 0.0446(16) 0.0335(14) 0.0003(12) 0.0013(12) -0.0121(13) C21 0.0455(17) 0.0541(17) 0.0341(14) 0.0038(12) -0.0006(12) -0.0265(14) C25 0.0508(19) 0.0490(17) 0.0419(15) -0.0065(12) 0.0022(13) -0.0288(15) C26 0.0382(17) 0.0520(17) 0.0469(16) -0.0073(13) 0.0002(13) -0.0180(14) C14 0.0381(16) 0.0444(16) 0.0406(15) -0.0081(12) 0.0020(12) -0.0092(13) C15 0.0414(17) 0.0481(16) 0.0366(14) -0.0044(12) 0.0067(12) -0.0133(13) N5 0.0403(15) 0.0615(16) 0.0552(15) -0.0087(13) 0.0086(12) 0.0015(12) C20 0.0394(17) 0.0643(19) 0.0397(15) 0.0008(13) -0.0042(13) -0.0221(14) C6 0.0561(19) 0.0538(18) 0.0325(14) -0.0009(12) 0.0011(13) -0.0227(15) C1 0.0473(18) 0.0494(17) 0.0399(14) -0.0002(12) 0.0047(13) -0.0255(14) C18 0.0508(19) 0.0440(16) 0.0479(16) 0.0057(13) 0.0029(14) -0.0215(14) O3 0.0728(17) 0.0427(13) 0.114(2) -0.0252(13) -0.0089(15) -0.0033(11) C2 0.063(2) 0.0527(18) 0.0503(17) -0.0037(14) -0.0007(15) -0.0344(16) C32 0.0512(19) 0.0517(18) 0.0518(17) -0.0102(14) 0.0057(14) -0.0166(15) C13 0.058(2) 0.0490(18) 0.0492(17) 0.0045(14) -0.0075(15) -0.0082(15) O1 0.102(2) 0.099(2) 0.0716(16) 0.0083(14) 0.0149(15) -0.0665(17) C10 0.057(2) 0.0540(18) 0.0498(17) -0.0077(14) 0.0118(15) -0.0234(15) C24 0.079(2) 0.0410(17) 0.0492(17) -0.0108(13) 0.0022(16) -0.0231(16) N8 0.0636(19) 0.069(2) 0.086(2) -0.0172(16) 0.0013(16) -0.0414(16) C28 0.062(2) 0.0435(18) 0.0626(19) -0.0068(14) 0.0160(16) -0.0150(15) C12 0.056(2) 0.052(2) 0.075(2) -0.0010(17) -0.0114(18) 0.0028(16) C31 0.054(2) 0.059(2) 0.0592(19) -0.0215(16) 0.0055(16) -0.0083(16) C30 0.0443(19) 0.0394(17) 0.080(2) -0.0138(15) -0.0126(17) -0.0036(14) C9 0.057(2) 0.078(2) 0.0478(17) -0.0052(16) 0.0173(15) -0.0302(18) C7 0.072(2) 0.0495(18) 0.0467(17) 0.0025(14) -0.0065(16) -0.0293(16) O5 0.170(3) 0.126(3) 0.107(2) -0.054(2) 0.013(2) -0.091(3) C8 0.063(2) 0.073(2) 0.0466(17) 0.0113(16) -0.0022(16) -0.0424(18) O7 0.104(2) 0.081(2) 0.129(3) -0.0343(18) 0.032(2) -0.0168(17) C23 0.095(3) 0.055(2) 0.081(2) -0.0176(18) 0.000(2) -0.043(2) O6 0.165(4) 0.107(2) 0.099(2) -0.0076(19) -0.029(2) -0.044(2) C29 0.073(2) 0.0406(18) 0.087(3) -0.0039(17) 0.011(2) -0.0167(16) C22 0.062(2) 0.083(3) 0.069(2) 0.0199(19) -0.0204(19) -0.0150(19) C33 0.133(4) 0.073(3) 0.112(4) -0.049(3) -0.027(3) -0.001(3) Cl2 0.0424(5) 0.0929(7) 0.0754(6) -0.0355(5) 0.0103(4) -0.0285(5) O9 0.086(2) 0.165(3) 0.101(2) -0.007(2) 0.0281(18) -0.067(2) O11 0.0659(19) 0.195(3) 0.0820(19) -0.003(2) -0.0003(15) -0.080(2) O10 0.096(3) 0.120(3) 0.192(4) -0.047(3) -0.003(3) 0.008(2) O8 0.114(3) 0.222(4) 0.135(3) -0.123(3) 0.054(2) -0.105(3) O4 0.160(3) 0.139(3) 0.122(3) -0.049(2) 0.086(2) -0.082(3) C11 0.092(3) 0.134(4) 0.091(3) 0.025(3) 0.023(3) -0.062(3) _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 Fe1 N6 2.231(2) . ? Fe1 N3 2.250(2) . ? Fe1 N9 2.266(2) . ? Fe1 N1 2.129(2) . ? Fe1 N4 2.140(2) . ? Fe1 N7 2.135(2) . ? Cl1 O5 1.416(3) . ? Cl1 O7 1.399(3) . ? Cl1 O6 1.419(3) . ? Cl1 O4 1.409(3) . ? N6 C16 1.429(3) . ? N6 C15 1.270(3) . ? N3 C5 1.426(3) . ? N3 C4 1.284(3) . ? N9 C27 1.426(3) . ? N9 C26 1.277(3) . ? N1 C3 1.331(3) . ? N1 C1 1.370(3) . ? N4 C14 1.325(3) . ? N4 C13 1.366(3) . ? N7 C25 1.315(4) . ? N7 C24 1.367(3) . ? N2 H2 0.8600 . ? N2 C3 1.336(3) . ? N2 C2 1.357(4) . ? C17 H17 0.9300 . ? C17 C16 1.387(3) . ? C17 C18 1.376(4) . ? C5 C6 1.386(4) . ? C5 C10 1.390(4) . ? C27 C32 1.377(4) . ? C27 C28 1.386(4) . ? C16 C21 1.380(4) . ? O2 C19 1.353(3) . ? O2 C22 1.421(4) . ? C4 H4 0.9300 . ? C4 C3 1.447(3) . ? C19 C20 1.393(4) . ? C19 C18 1.388(4) . ? C21 H21 0.9300 . ? C21 C20 1.380(4) . ? C25 C26 1.440(4) . ? C25 N8 1.341(4) . ? C26 H26 0.9300 . ? C14 C15 1.448(4) . ? C14 N5 1.339(3) . ? C15 H15 0.9300 . ? N5 H5 0.8600 . ? N5 C12 1.348(4) . ? C20 H20 0.9300 . ? C6 H6 0.9300 . ? C6 C7 1.381(4) . ? C1 H1 0.9300 . ? C1 C2 1.348(4) . ? C18 H18 0.9300 . ? O3 C30 1.362(4) . ? O3 C33 1.437(5) . ? C2 H2A 0.9300 . ? C32 H32 0.9300 . ? C32 C31 1.381(4) . ? C13 H13 0.9300 . ? C13 C12 1.356(4) . ? O1 C8 1.373(3) . ? O1 C11 1.394(5) . ? C10 H10 0.9300 . ? C10 C9 1.386(4) . ? C24 H24 0.9300 . ? C24 C23 1.350(5) . ? N8 H8 0.8600 . ? N8 C23 1.358(5) . ? C28 H28 0.9300 . ? C28 C29 1.366(4) . ? C12 H12 0.9300 . ? C31 H31 0.9300 . ? C31 C30 1.369(5) . ? C30 C29 1.384(5) . ? C9 H9 0.9300 . ? C9 C8 1.382(5) . ? C7 H7 0.9300 . ? C7 C8 1.368(5) . ? C23 H23 0.9300 . ? C29 H29 0.9300 . ? C22 H22C 0.9600 . ? C22 H22B 0.9600 . ? C22 H22A 0.9600 . ? C33 H33C 0.9600 . ? C33 H33B 0.9600 . ? C33 H33A 0.9600 . ? Cl2 O9 1.449(3) . ? Cl2 O11 1.384(2) . ? Cl2 O10 1.372(3) . ? Cl2 O8 1.417(3) . ? C11 H11A 0.9600 . ? C11 H11C 0.9600 . ? C11 H11B 0.9600 . ? 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 N6 Fe1 N3 167.90(8) . . ? N6 Fe1 N9 97.81(8) . . ? N6 C15 C14 117.3(2) . . ? N6 C15 H15 121.4 . . ? N3 Fe1 N9 81.51(8) . . ? N3 C4 H4 121.4 . . ? N3 C4 C3 117.2(2) . . ? N9 C26 C25 116.9(3) . . ? N9 C26 H26 121.6 . . ? N1 Fe1 N6 91.03(8) . . ? N1 Fe1 N3 76.93(8) . . ? N1 Fe1 N9 91.29(8) . . ? N1 Fe1 N4 98.25(8) . . ? N1 Fe1 N7 165.85(9) . . ? N1 C3 N2 110.9(2) . . ? N1 C3 C4 121.3(2) . . ? N1 C1 H1 125.0 . . ? N4 Fe1 N6 77.32(8) . . ? N4 Fe1 N3 105.26(8) . . ? N4 Fe1 N9 169.32(8) . . ? N4 C14 C15 122.0(2) . . ? N4 C14 N5 110.6(2) . . ? N4 C13 H13 125.3 . . ? N7 Fe1 N6 96.29(8) . . ? N7 Fe1 N3 95.24(8) . . ? N7 Fe1 N9 75.76(8) . . ? N7 Fe1 N4 95.17(9) . . ? N7 C25 C26 121.3(2) . . ? N7 C25 N8 110.6(3) . . ? N7 C24 H24 125.6 . . ? N2 C3 C4 127.8(2) . . ? N2 C2 H2A 126.9 . . ? C17 C16 N6 122.2(2) . . ? C17 C18 C19 120.9(2) . . ? C17 C18 H18 119.5 . . ? C5 N3 Fe1 127.62(17) . . ? C5 C6 H6 119.6 . . ? C5 C10 H10 119.8 . . ? C27 N9 Fe1 125.85(17) . . ? C27 C32 H32 119.7 . . ? C27 C32 C31 120.5(3) . . ? C27 C28 H28 120.3 . . ? C16 N6 Fe1 127.26(17) . . ? C16 C17 H17 120.1 . . ? C16 C21 H21 119.4 . . ? O2 C19 C20 124.6(3) . . ? O2 C19 C18 116.0(2) . . ? O2 C22 H22C 109.5 . . ? O2 C22 H22B 109.5 . . ? O2 C22 H22A 109.5 . . ? C4 N3 Fe1 111.28(16) . . ? C4 N3 C5 119.6(2) . . ? C3 N1 Fe1 111.27(16) . . ? C3 N1 C1 105.0(2) . . ? C3 N2 H2 126.1 . . ? C3 N2 C2 107.9(2) . . ? C3 C4 H4 121.4 . . ? C19 O2 C22 118.0(2) . . ? C19 C20 H20 120.3 . . ? C19 C18 H18 119.5 . . ? C21 C16 N6 118.4(2) . . ? C21 C16 C17 119.4(2) . . ? C21 C20 C19 119.3(3) . . ? C21 C20 H20 120.3 . . ? C25 N7 Fe1 113.12(18) . . ? C25 N7 C24 106.4(2) . . ? C25 C26 H26 121.6 . . ? C25 N8 H8 126.3 . . ? C25 N8 C23 107.3(3) . . ? C26 N9 Fe1 112.30(19) . . ? C26 N9 C27 120.0(2) . . ? C14 N4 Fe1 110.51(17) . . ? C14 N4 C13 105.6(2) . . ? C14 C15 H15 121.4 . . ? C14 N5 H5 126.0 . . ? C14 N5 C12 108.0(3) . . ? C15 N6 Fe1 111.84(17) . . ? C15 N6 C16 120.0(2) . . ? N5 C14 C15 127.4(2) . . ? N5 C12 C13 106.4(3) . . ? N5 C12 H12 126.8 . . ? C20 C21 C16 121.2(2) . . ? C20 C21 H21 119.4 . . ? C6 C5 N3 118.2(2) . . ? C6 C5 C10 118.6(2) . . ? C6 C7 H7 119.9 . . ? C1 N1 Fe1 142.25(18) . . ? C1 C2 N2 106.2(2) . . ? C1 C2 H2A 126.9 . . ? C18 C17 H17 120.1 . . ? C18 C17 C16 119.8(3) . . ? C18 C19 C20 119.3(2) . . ? O3 C30 C31 125.2(3) . . ? O3 C30 C29 115.6(3) . . ? O3 C33 H33C 109.5 . . ? O3 C33 H33B 109.5 . . ? O3 C33 H33A 109.5 . . ? C2 N2 H2 126.1 . . ? C2 C1 N1 110.0(2) . . ? C2 C1 H1 125.0 . . ? C32 C27 N9 121.2(2) . . ? C32 C27 C28 119.4(3) . . ? C32 C31 H31 119.9 . . ? C13 N4 Fe1 143.5(2) . . ? C13 C12 H12 126.8 . . ? O1 C8 C9 124.7(3) . . ? O1 C11 H11A 109.5 . . ? O1 C11 H11C 109.5 . . ? O1 C11 H11B 109.5 . . ? C10 C5 N3 123.3(3) . . ? C10 C9 H9 120.0 . . ? C24 N7 Fe1 140.5(2) . . ? C24 C23 N8 106.8(3) . . ? C24 C23 H23 126.6 . . ? N8 C25 C26 128.0(3) . . ? N8 C23 H23 126.6 . . ? C28 C27 N9 119.2(3) . . ? C28 C29 C30 121.2(3) . . ? C28 C29 H29 119.4 . . ? C12 N5 H5 126.0 . . ? C12 C13 N4 109.4(3) . . ? C12 C13 H13 125.3 . . ? C31 C32 H32 119.7 . . ? C31 C30 C29 119.1(3) . . ? C30 O3 C33 117.2(3) . . ? C30 C31 C32 120.1(3) . . ? C30 C31 H31 119.9 . . ? C30 C29 H29 119.4 . . ? C9 C10 C5 120.4(3) . . ? C9 C10 H10 119.8 . . ? C7 C6 C5 120.8(3) . . ? C7 C6 H6 119.6 . . ? C7 C8 O1 115.2(3) . . ? C7 C8 C9 120.1(3) . . ? O5 Cl1 O6 108.0(2) . . ? C8 O1 C11 118.5(3) . . ? C8 C9 C10 119.9(3) . . ? C8 C9 H9 120.0 . . ? C8 C7 C6 120.2(3) . . ? C8 C7 H7 119.9 . . ? O7 Cl1 O5 112.1(2) . . ? O7 Cl1 O6 107.6(2) . . ? O7 Cl1 O4 109.6(2) . . ? C23 C24 N7 108.9(3) . . ? C23 C24 H24 125.6 . . ? C23 N8 H8 126.3 . . ? C29 C28 C27 119.5(3) . . ? C29 C28 H28 120.3 . . ? H22C C22 H22B 109.5 . . ? H22C C22 H22A 109.5 . . ? H22B C22 H22A 109.5 . . ? H33C C33 H33B 109.5 . . ? H33C C33 H33A 109.5 . . ? H33B C33 H33A 109.5 . . ? O11 Cl2 O9 108.75(18) . . ? O11 Cl2 O8 108.66(19) . . ? O10 Cl2 O9 107.5(2) . . ? O10 Cl2 O11 114.5(2) . . ? O10 Cl2 O8 108.3(3) . . ? O8 Cl2 O9 109.0(2) . . ? O4 Cl1 O5 110.6(2) . . ? O4 Cl1 O6 109.0(3) . . ? H11A C11 H11C 109.5 . . ? H11A C11 H11B 109.5 . . ? H11C C11 H11B 109.5 . . ? ####END data_L _database_code_depnum_ccdc_archive 'CCDC 894555' #TrackingRef '- JRT.cif' _audit_creation_date 2012-05-10 _audit_creation_method ; Olex2 1.2 (compiled May 4 2012 14:03:18, GUI svn.r4222) ; _chemical_formula_moiety 'C11 H11 N3 O' _chemical_formula_sum 'C11 H11 N3 O' _chemical_formula_weight 201.23 _chemical_absolute_configuration unk _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_H-M_alt 'P 21 21 21' _space_group_name_Hall 'P 2ac 2ab' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, -y, z+1/2' 3 'x+1/2, -y+1/2, -z' 4 '-x, y+1/2, -z+1/2' _cell_length_a 5.0830(2) _cell_length_b 8.1957(4) _cell_length_c 24.4759(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1019.64(8) _cell_formula_units_Z 4 _cell_measurement_reflns_used 9296 _cell_measurement_temperature 113(2) _cell_measurement_theta_max 30.49 _cell_measurement_theta_min 2.62 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_T_max 0.9792 _exptl_absorpt_correction_T_min 0.9409 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details SADABS _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.311 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 424 _exptl_crystal_size_max 0.7 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.24 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0457 _diffrn_reflns_av_unetI/netI 0.0196 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_number 17679 _diffrn_reflns_theta_full 25.04 _diffrn_reflns_theta_max 25.04 _diffrn_reflns_theta_min 2.62 _diffrn_ambient_temperature 113.0 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_current 30.0 _diffrn_source_power 1.35 _diffrn_source_voltage 45.0 _diffrn_standards_number 0 _reflns_number_gt 1680 _reflns_number_total 1804 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ? _computing_data_collection ? _computing_data_reduction 'SAINT v7.53A (Bruker, 2008)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XLMP, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; XS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.243 _refine_diff_density_min -0.227 _refine_diff_density_rms 0.056 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(3) _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.148 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 137 _refine_ls_number_reflns 1804 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0497 _refine_ls_R_factor_gt 0.0464 _refine_ls_restrained_S_all 1.148 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0522P)^2^+0.8566P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1212 _refine_ls_wR_factor_ref 0.1232 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 O1 O 0.4356(4) 0.4368(2) 0.03705(8) 0.0292(5) Uani 1 1 d . . . N3 N 0.3607(4) 1.0388(3) 0.14301(9) 0.0219(5) Uani 1 1 d . . . N1 N -0.0960(4) 1.3386(3) 0.19151(9) 0.0245(5) Uani 1 1 d . . . C10 C 0.5709(5) 0.7792(3) 0.13073(11) 0.0229(6) Uani 1 1 d . . . H10 H 0.6867 0.8089 0.1584 0.027 Uiso 1 1 calc R . . C4 C 0.1418(5) 1.1110(3) 0.14822(10) 0.0206(6) Uani 1 1 d . . . H4 H -0.0090 1.0660 0.1329 0.025 Uiso 1 1 calc R . . N2 N 0.3370(4) 1.3434(3) 0.19823(9) 0.0211(5) Uani 1 1 d . . . H2 H 0.4990 1.3153 0.1944 0.025 Uiso 1 1 calc R . . C5 C 0.3731(5) 0.8875(3) 0.11451(10) 0.0207(6) Uani 1 1 d . . . C8 C 0.4264(6) 0.5831(3) 0.06471(11) 0.0228(6) Uani 1 1 d . . . C3 C 0.1254(5) 1.2642(3) 0.17819(10) 0.0193(5) Uani 1 1 d . . . C6 C 0.2059(5) 0.8420(3) 0.07215(11) 0.0228(6) Uani 1 1 d . . . H6 H 0.0757 0.9136 0.0604 0.027 Uiso 1 1 calc R . . C2 C 0.2451(6) 1.4771(4) 0.22595(11) 0.0262(6) Uani 1 1 d . . . H2A H 0.3449 1.5551 0.2442 0.031 Uiso 1 1 calc R . . C9 C 0.5963(6) 0.6273(3) 0.10583(11) 0.0234(6) Uani 1 1 d . . . H9 H 0.7279 0.5559 0.1170 0.028 Uiso 1 1 calc R . . C7 C 0.2314(6) 0.6909(3) 0.04726(11) 0.0247(6) Uani 1 1 d . . . H7 H 0.1188 0.6615 0.0190 0.030 Uiso 1 1 calc R . . C11 C 0.6469(6) 0.3293(3) 0.05048(13) 0.0340(7) Uani 1 1 d . . . H11A H 0.6416 0.2358 0.0269 0.051 Uiso 1 1 calc R . . H11B H 0.6299 0.2948 0.0878 0.051 Uiso 1 1 calc R . . H11C H 0.8114 0.3852 0.0458 0.051 Uiso 1 1 calc R . . C1 C -0.0201(6) 1.4728(4) 0.22140(12) 0.0272(7) Uani 1 1 d . . . H1 H -0.1344 1.5494 0.2363 0.033 Uiso 1 1 calc R . . 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 O1 0.0359(12) 0.0161(9) 0.0357(10) -0.0087(9) -0.0032(9) 0.0031(8) N3 0.0224(12) 0.0141(10) 0.0293(12) -0.0009(9) -0.0003(10) 0.0017(10) N1 0.0172(11) 0.0207(11) 0.0355(13) -0.0064(10) -0.0039(10) 0.0019(10) C10 0.0184(13) 0.0176(12) 0.0325(14) -0.0034(11) -0.0019(11) -0.0011(11) C4 0.0159(13) 0.0162(12) 0.0298(13) -0.0022(10) -0.0009(10) -0.0022(11) N2 0.0130(11) 0.0167(11) 0.0337(12) -0.0033(9) 0.0011(9) 0.0051(9) C5 0.0209(13) 0.0140(12) 0.0273(13) -0.0007(10) 0.0014(11) -0.0027(11) C8 0.0290(15) 0.0133(12) 0.0261(13) -0.0016(10) 0.0050(11) -0.0020(11) C3 0.0134(12) 0.0167(12) 0.0278(13) 0.0025(11) 0.0003(11) -0.0007(10) C6 0.0191(13) 0.0191(13) 0.0303(14) 0.0002(12) 0.0002(11) 0.0036(11) C2 0.0243(14) 0.0192(15) 0.0352(15) -0.0104(12) -0.0004(12) 0.0005(11) C9 0.0215(13) 0.0162(12) 0.0324(14) -0.0011(11) 0.0004(12) 0.0044(11) C7 0.0269(14) 0.0202(14) 0.0270(13) -0.0036(11) -0.0014(12) -0.0020(12) C11 0.0411(17) 0.0188(14) 0.0420(16) -0.0077(12) -0.0012(15) 0.0092(14) C1 0.0245(15) 0.0204(14) 0.0368(15) -0.0095(13) 0.0009(12) 0.0069(11) _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 O1 C8 1.378(3) . ? O1 C11 1.427(3) . ? N3 C4 1.267(3) . ? N3 C5 1.424(3) . ? N1 C3 1.321(3) . ? N1 C1 1.376(4) . ? C10 H10 0.9300 . ? C10 C5 1.399(4) . ? C10 C9 1.392(4) . ? C4 H4 0.9300 . ? C4 C3 1.457(3) . ? N2 H2 0.8600 . ? N2 C3 1.349(3) . ? N2 C2 1.371(3) . ? C5 C6 1.392(4) . ? C8 C9 1.375(4) . ? C8 C7 1.394(4) . ? C6 H6 0.9300 . ? C6 C7 1.386(4) . ? C2 H2A 0.9300 . ? C2 C1 1.353(4) . ? C9 H9 0.9300 . ? C7 H7 0.9300 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C1 H1 0.9300 . ? 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 C8 O1 C11 116.7(2) . . ? C4 N3 C5 119.7(2) . . ? C3 N1 C1 105.1(2) . . ? C5 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C9 C10 C5 120.6(3) . . ? N3 C4 H4 119.9 . . ? N3 C4 C3 120.3(2) . . ? C3 C4 H4 119.9 . . ? C3 N2 H2 126.5 . . ? C3 N2 C2 107.0(2) . . ? C2 N2 H2 126.5 . . ? C10 C5 N3 116.5(2) . . ? C6 C5 N3 124.8(2) . . ? C6 C5 C10 118.7(2) . . ? O1 C8 C7 115.2(2) . . ? C9 C8 O1 124.6(2) . . ? C9 C8 C7 120.3(2) . . ? N1 C3 C4 124.8(2) . . ? N1 C3 N2 111.6(2) . . ? N2 C3 C4 123.5(2) . . ? C5 C6 H6 119.7 . . ? C7 C6 C5 120.6(2) . . ? C7 C6 H6 119.7 . . ? N2 C2 H2A 126.9 . . ? C1 C2 N2 106.1(3) . . ? C1 C2 H2A 126.9 . . ? C10 C9 H9 120.1 . . ? C8 C9 C10 119.9(3) . . ? C8 C9 H9 120.1 . . ? C8 C7 H7 120.1 . . ? C6 C7 C8 119.9(2) . . ? C6 C7 H7 120.1 . . ? O1 C11 H11A 109.5 . . ? O1 C11 H11B 109.5 . . ? O1 C11 H11C 109.5 . . ? H11A C11 H11B 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N1 C1 H1 124.9 . . ? C2 C1 N1 110.1(3) . . ? C2 C1 H1 124.9 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 N1 0.86 2.07 2.887(3) 158.7 1_655