#------------------------------------------------------------------------------ #$Date: 2021-07-05 20:43:40 +0300 (Mon, 05 Jul 2021) $ #$Revision: 267192 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/70/73/7707357.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7707357 loop_ _publ_author_name 'Wang, Kuiyuan' 'Prior, Timothy J.' 'Hughes, David L.' 'Arbaoui, Abdessamad' 'Redshaw, Carl' _publ_section_title ; Coordination chemistry of [2 + 2] Schiff-base macrocycles derived from the dianilines [(2-NH2C6H4)2X] (X = CH2CH2, O): structural studies and ROP capability towards cyclic esters. ; _journal_issue 23 _journal_name_full 'Dalton transactions (Cambridge, England : 2003)' _journal_page_first 8057 _journal_page_last 8069 _journal_paper_doi 10.1039/d1dt00711d _journal_volume 50 _journal_year 2021 _chemical_formula_moiety ; C28 H32 Br2 Fe2 N2 O6, 2(C2 H3 N) ; _chemical_formula_sum 'C32 H38 Br2 Fe2 N4 O6' _chemical_formula_weight 846.18 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2021-02-18 deposited with the CCDC. 2021-05-04 downloaded from the CCDC. ; _cell_angle_alpha 101.2110(10) _cell_angle_beta 102.4660(10) _cell_angle_gamma 97.4090(10) _cell_formula_units_Z 1 _cell_length_a 8.51990(10) _cell_length_b 9.20980(10) _cell_length_c 12.1881(2) _cell_measurement_reflns_used 17670 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 70.0970 _cell_measurement_theta_min 3.8250 _cell_volume 901.29(2) _computing_cell_refinement 'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)' _computing_data_collection 'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)' _computing_data_reduction 'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)' _computing_molecular_graphics 'Mercury, ORTEP' _computing_publication_material 'SHELXL, ciftab' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean 10.000 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.985 _diffrn_measurement_device_type 'XtaLAB AFC11 (RCD3): quarter-chi single' _diffrn_measurement_method \w-scans _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0342 _diffrn_reflns_av_unetI/netI 0.0152 _diffrn_reflns_Laue_measured_fraction_full 0.994 _diffrn_reflns_Laue_measured_fraction_max 0.985 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 32046 _diffrn_reflns_point_group_measured_fraction_full 0.994 _diffrn_reflns_point_group_measured_fraction_max 0.985 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 70.343 _diffrn_reflns_theta_min 3.816 _diffrn_source 'Rotating-anode X-ray tube' _exptl_absorpt_coefficient_mu 9.433 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.64633 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.559 _exptl_crystal_description block _exptl_crystal_F_000 428 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: Acetonitrile' _exptl_crystal_size_max 0.030 _exptl_crystal_size_mid 0.020 _exptl_crystal_size_min 0.010 _refine_diff_density_max 0.413 _refine_diff_density_min -0.687 _refine_diff_density_rms 0.067 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_hydrogen_treatment refxyz _refine_ls_matrix_type full _refine_ls_number_parameters 217 _refine_ls_number_reflns 3387 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.091 _refine_ls_R_factor_all 0.0312 _refine_ls_R_factor_gt 0.0299 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0509P)^2^+0.4803P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0807 _refine_ls_wR_factor_ref 0.0822 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3268 _reflns_number_total 3387 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1dt00711d2.cif _cod_data_source_block shelx _cod_depositor_comments 'Adding full bibliography for 7707347--7707359.cif.' _cod_database_code 7707357 _shelx_shelxl_version_number 2018/3 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_min 0.765 _shelx_estimated_absorpt_t_max 0.912 _shelx_res_file ; TITL shelxt_a.res in P-1 shelx.res created by SHELXL-2018/3 at 21:42:45 on 17-Feb-2021 CELL 1.54178 8.5199 9.2098 12.1881 101.211 102.466 97.409 ZERR 1.00 0.0001 0.0001 0.0002 0.001 0.001 0.001 LATT 1 SFAC C H N O FE BR UNIT 32 38 4 6 2 2 MERG 2 FMAP 2 PLAN 8 ACTA BOND $H size 0.03 0.02 0.01 LIST 6 L.S. 4 TEMP -173.00 WGHT 0.050900 0.480300 FVAR 0.66580 C1 1 0.382117 0.110208 0.319927 11.00000 0.02286 0.01903 = 0.02243 0.00370 0.00492 0.00031 C2 1 0.347997 0.258867 0.332194 11.00000 0.02645 0.01892 = 0.02490 0.00275 0.00531 0.00157 C3 1 0.294352 0.317505 0.234531 11.00000 0.02964 0.01929 = 0.02624 0.00385 0.00559 0.00230 AFIX 44 H3 2 0.270859 0.420337 0.246552 11.00000 -1.20000 AFIX 0 C4 1 0.273491 0.236239 0.122641 11.00000 0.02702 0.02295 = 0.02353 0.00526 0.00422 0.00220 C5 1 0.302161 0.089071 0.110605 11.00000 0.02943 0.02347 = 0.02226 0.00225 0.00622 0.00284 AFIX 44 H5 2 0.285777 0.030624 0.036586 11.00000 -1.20000 AFIX 0 C6 1 0.354309 0.024533 0.204005 11.00000 0.02767 0.01914 = 0.02430 0.00219 0.00531 0.00262 C7 1 0.359568 0.358353 0.441541 11.00000 0.03198 0.01668 = 0.02695 0.00274 0.00618 0.00402 AFIX 44 H7 2 0.319933 0.450566 0.438486 11.00000 -1.20000 AFIX 0 C8 1 0.372537 -0.130848 0.172962 11.00000 0.02947 0.02171 = 0.02288 0.00073 0.00533 0.00395 AFIX 44 H8 2 0.347341 -0.176621 0.089598 11.00000 -1.20000 AFIX 0 C9 1 0.215956 0.298068 0.015261 11.00000 0.03292 0.02431 = 0.02384 0.00709 0.00626 0.00438 C10 1 0.213819 0.466013 0.047428 11.00000 0.04478 0.02811 = 0.02992 0.00871 0.00602 0.00821 AFIX 137 H10A 2 0.180069 0.502318 -0.022965 11.00000 -1.50000 H10B 2 0.323406 0.519828 0.090419 11.00000 -1.50000 H10C 2 0.136608 0.483925 0.095521 11.00000 -1.50000 AFIX 0 C11 1 0.332352 0.272334 -0.064307 11.00000 0.04390 0.03680 = 0.03164 0.01290 0.01508 0.00843 AFIX 137 H11A 2 0.331968 0.164325 -0.088187 11.00000 -1.50000 H11B 2 0.443225 0.324259 -0.022732 11.00000 -1.50000 H11C 2 0.296012 0.312024 -0.132691 11.00000 -1.50000 AFIX 0 C12 1 0.043394 0.213089 -0.049575 11.00000 0.03685 0.03276 = 0.03026 0.00771 0.00124 0.00313 AFIX 137 H12A 2 -0.031292 0.228947 0.000768 11.00000 -1.50000 H12B 2 0.045536 0.105388 -0.072041 11.00000 -1.50000 H12C 2 0.005850 0.250719 -0.118817 11.00000 -1.50000 AFIX 0 C13 1 0.159562 0.022863 0.631784 11.00000 0.03657 0.02801 = 0.02189 0.00451 0.00357 0.00655 C14 1 0.009386 -0.052115 0.650166 11.00000 0.03406 0.03807 = 0.03503 0.01111 0.01074 0.00399 AFIX 137 H14A 2 -0.074082 0.011509 0.640877 11.00000 -1.50000 H14B 2 0.030364 -0.069765 0.728341 11.00000 -1.50000 H14C 2 -0.029197 -0.148552 0.593653 11.00000 -1.50000 AFIX 0 C15 1 0.244355 0.693632 0.786256 11.00000 0.04000 0.04461 = 0.03026 0.01009 0.01037 0.00773 C16 1 0.229026 0.562091 0.694183 11.00000 0.06183 0.03916 = 0.04349 -0.00181 0.01976 0.00157 AFIX 137 H16A 2 0.226209 0.593232 0.621438 11.00000 -1.50000 H16B 2 0.127877 0.492611 0.686474 11.00000 -1.50000 H16C 2 0.322652 0.511712 0.712539 11.00000 -1.50000 AFIX 0 N1 3 0.274574 0.079852 0.614699 11.00000 0.03419 0.02839 = 0.02784 0.00348 0.00869 0.00414 N2 3 0.255682 0.796657 0.858079 11.00000 0.06802 0.05225 = 0.03362 0.00118 0.01142 0.01683 O1 4 0.414990 0.338579 0.539476 11.00000 0.03695 0.01941 = 0.02366 0.00190 0.00579 0.00565 O2 4 0.431596 0.054050 0.408839 11.00000 0.03324 0.01672 = 0.02080 0.00324 0.00544 0.00406 O3 4 0.415840 -0.213237 0.238179 11.00000 0.03742 0.01922 = 0.02414 0.00139 0.00637 0.00581 FE1 5 0.513954 0.161030 0.584920 11.00000 0.03149 0.01598 = 0.02031 0.00243 0.00517 0.00379 BR1 6 0.807454 0.283649 0.586130 11.00000 0.03354 0.02172 = 0.04045 0.00520 0.01011 0.00279 HKLF 4 REM shelxt_a.res in P-1 REM wR2 = 0.0822, GooF = S = 1.091, Restrained GooF = 1.091 for all data REM R1 = 0.0299 for 3268 Fo > 4sig(Fo) and 0.0312 for all 3387 data REM 217 parameters refined using 0 restraints END WGHT 0.0509 0.4802 REM Highest difference peak 0.413, deepest hole -0.687, 1-sigma level 0.067 Q1 1 0.6315 0.2839 0.5878 11.00000 0.05 0.41 Q2 1 0.9226 0.2167 0.5412 11.00000 0.05 0.40 Q3 1 0.6885 0.1624 0.5860 11.00000 0.05 0.40 Q4 1 0.9731 0.2630 0.5981 11.00000 0.05 0.34 Q5 1 0.8958 0.2415 0.6616 11.00000 0.05 0.32 Q6 1 0.3613 -0.0363 0.1989 11.00000 0.05 0.31 Q7 1 0.7610 0.4138 0.6100 11.00000 0.05 0.30 Q8 1 0.2546 0.2666 0.0798 11.00000 0.05 0.30 ; _shelx_res_checksum 90588 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.3821(3) 0.1102(2) 0.31993(18) 0.0220(4) Uani 1 1 d . . . . . C2 C 0.3480(3) 0.2589(2) 0.33219(19) 0.0241(4) Uani 1 1 d . . . . . C3 C 0.2944(3) 0.3175(3) 0.23453(19) 0.0257(5) Uani 1 1 d . . . . . H3 H 0.2709(7) 0.420(3) 0.2466(4) 0.031 Uiso 1 1 calc R U . . . C4 C 0.2735(3) 0.2362(3) 0.12264(19) 0.0250(5) Uani 1 1 d . . . . . C5 C 0.3022(3) 0.0891(3) 0.11060(19) 0.0257(5) Uani 1 1 d . . . . . H5 H 0.2858(6) 0.0306(19) 0.037(2) 0.031 Uiso 1 1 calc R U . . . C6 C 0.3543(3) 0.0245(2) 0.20401(19) 0.0244(5) Uani 1 1 d . . . . . C7 C 0.3596(3) 0.3584(2) 0.44154(19) 0.0257(5) Uani 1 1 d . . . . . H7 H 0.3199(13) 0.451(3) 0.4385(2) 0.031 Uiso 1 1 calc R U . . . C8 C 0.3725(3) -0.1308(2) 0.17296(19) 0.0255(5) Uani 1 1 d . . . . . H8 H 0.3473(8) -0.1766(13) 0.090(2) 0.031 Uiso 1 1 calc R U . . . C9 C 0.2160(3) 0.2981(3) 0.01526(19) 0.0270(5) Uani 1 1 d . . . . . C10 C 0.2138(3) 0.4660(3) 0.0474(2) 0.0343(5) Uani 1 1 d . . . . . H10A H 0.180069 0.502318 -0.022965 0.051 Uiso 1 1 calc R U . . . H10B H 0.323406 0.519828 0.090419 0.051 Uiso 1 1 calc R U . . . H10C H 0.136608 0.483925 0.095521 0.051 Uiso 1 1 calc R U . . . C11 C 0.3324(3) 0.2723(3) -0.0643(2) 0.0357(6) Uani 1 1 d . . . . . H11A H 0.331968 0.164325 -0.088187 0.054 Uiso 1 1 calc R U . . . H11B H 0.443225 0.324259 -0.022732 0.054 Uiso 1 1 calc R U . . . H11C H 0.296012 0.312024 -0.132691 0.054 Uiso 1 1 calc R U . . . C12 C 0.0434(3) 0.2131(3) -0.0496(2) 0.0346(6) Uani 1 1 d . . . . . H12A H -0.031292 0.228947 0.000768 0.052 Uiso 1 1 calc R U . . . H12B H 0.045536 0.105388 -0.072041 0.052 Uiso 1 1 calc R U . . . H12C H 0.005850 0.250719 -0.118817 0.052 Uiso 1 1 calc R U . . . C13 C 0.1596(3) 0.0229(3) 0.63178(19) 0.0295(5) Uani 1 1 d . . . . . C14 C 0.0094(3) -0.0521(3) 0.6502(2) 0.0352(6) Uani 1 1 d . . . . . H14A H -0.074082 0.011509 0.640877 0.053 Uiso 1 1 calc R U . . . H14B H 0.030364 -0.069765 0.728341 0.053 Uiso 1 1 calc R U . . . H14C H -0.029197 -0.148552 0.593653 0.053 Uiso 1 1 calc R U . . . C15 C 0.2444(3) 0.6936(3) 0.7863(2) 0.0378(6) Uani 1 1 d . . . . . C16 C 0.2290(4) 0.5621(3) 0.6942(3) 0.0494(7) Uani 1 1 d . . . . . H16A H 0.226209 0.593232 0.621438 0.074 Uiso 1 1 calc R U . . . H16B H 0.127877 0.492611 0.686474 0.074 Uiso 1 1 calc R U . . . H16C H 0.322652 0.511712 0.712539 0.074 Uiso 1 1 calc R U . . . N1 N 0.2746(3) 0.0799(2) 0.61470(17) 0.0305(4) Uani 1 1 d . . . . . N2 N 0.2557(4) 0.7967(3) 0.8581(2) 0.0521(7) Uani 1 1 d . . . . . O1 O 0.4150(2) 0.33858(17) 0.53948(13) 0.0273(3) Uani 1 1 d . . . . . O2 O 0.43160(19) 0.05405(16) 0.40884(12) 0.0240(3) Uani 1 1 d . . . . . O3 O 0.4158(2) -0.21324(17) 0.23818(13) 0.0276(3) Uani 1 1 d . . . . . Fe1 Fe 0.51395(4) 0.16103(4) 0.58492(3) 0.02308(11) Uani 1 1 d . . . . . Br1 Br 0.80745(3) 0.28365(3) 0.58613(2) 0.03222(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 C1 0.0229(11) 0.0190(10) 0.0224(10) 0.0037(8) 0.0049(8) 0.0003(8) C2 0.0264(11) 0.0189(10) 0.0249(11) 0.0028(8) 0.0053(9) 0.0016(8) C3 0.0296(12) 0.0193(11) 0.0262(11) 0.0039(9) 0.0056(9) 0.0023(9) C4 0.0270(12) 0.0229(11) 0.0235(11) 0.0053(9) 0.0042(9) 0.0022(9) C5 0.0294(12) 0.0235(11) 0.0223(11) 0.0022(9) 0.0062(9) 0.0028(9) C6 0.0277(12) 0.0191(10) 0.0243(11) 0.0022(8) 0.0053(9) 0.0026(9) C7 0.0320(12) 0.0167(10) 0.0269(11) 0.0027(9) 0.0062(9) 0.0040(9) C8 0.0295(12) 0.0217(11) 0.0229(11) 0.0007(9) 0.0053(9) 0.0040(9) C9 0.0329(13) 0.0243(11) 0.0238(11) 0.0071(9) 0.0063(9) 0.0044(9) C10 0.0448(15) 0.0281(12) 0.0299(12) 0.0087(10) 0.0060(10) 0.0082(11) C11 0.0439(15) 0.0368(14) 0.0316(12) 0.0129(11) 0.0151(11) 0.0084(12) C12 0.0368(14) 0.0328(13) 0.0303(12) 0.0077(10) 0.0012(10) 0.0031(11) C13 0.0366(14) 0.0280(12) 0.0219(11) 0.0045(9) 0.0036(9) 0.0065(10) C14 0.0341(14) 0.0381(14) 0.0350(13) 0.0111(11) 0.0107(11) 0.0040(11) C15 0.0400(15) 0.0446(15) 0.0303(13) 0.0101(12) 0.0104(11) 0.0077(12) C16 0.062(2) 0.0392(16) 0.0435(16) -0.0018(13) 0.0198(14) 0.0016(14) N1 0.0342(12) 0.0284(10) 0.0278(10) 0.0035(8) 0.0087(9) 0.0041(9) N2 0.0680(18) 0.0523(16) 0.0336(13) 0.0012(12) 0.0114(12) 0.0168(13) O1 0.0369(9) 0.0194(7) 0.0237(8) 0.0019(6) 0.0058(7) 0.0057(6) O2 0.0332(9) 0.0167(7) 0.0208(7) 0.0032(6) 0.0054(6) 0.0041(6) O3 0.0374(9) 0.0192(8) 0.0241(8) 0.0014(6) 0.0064(7) 0.0058(7) Fe1 0.0315(2) 0.01598(18) 0.02031(18) 0.00243(14) 0.00517(15) 0.00379(14) Br1 0.03354(17) 0.02172(14) 0.04045(17) 0.00520(11) 0.01011(11) 0.00279(10) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe -1.1336 3.1974 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 C1 C2 121.99(19) . . ? O2 C1 C6 121.99(19) . . ? C2 C1 C6 116.00(19) . . ? C3 C2 C1 121.0(2) . . ? C3 C2 C7 115.0(2) . . ? C1 C2 C7 123.9(2) . . ? C4 C3 C2 122.8(2) . . ? C4 C3 H3 118.6 . . ? C2 C3 H3 118.6 . . ? C3 C4 C5 116.1(2) . . ? C3 C4 C9 123.6(2) . . ? C5 C4 C9 120.2(2) . . ? C4 C5 C6 123.6(2) . . ? C4 C5 H5 118.2 . . ? C6 C5 H5 118.2 . . ? C5 C6 C1 120.4(2) . . ? C5 C6 C8 114.97(19) . . ? C1 C6 C8 124.7(2) . . ? O1 C7 C2 127.6(2) . . ? O1 C7 H7 116.2 . . ? C2 C7 H7 116.2 . . ? O3 C8 C6 127.9(2) . . ? O3 C8 H8 116.1 . . ? C6 C8 H8 116.1 . . ? C10 C9 C12 109.6(2) . . ? C10 C9 C4 111.61(19) . . ? C12 C9 C4 108.70(19) . . ? C10 C9 C11 108.4(2) . . ? C12 C9 C11 109.1(2) . . ? C4 C9 C11 109.39(19) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N1 C13 C14 178.3(3) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N2 C15 C16 179.7(4) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C13 N1 Fe1 171.5(2) . . ? C7 O1 Fe1 128.99(15) . . ? C1 O2 Fe1 129.84(13) . . ? C1 O2 Fe1 129.71(13) . 2_656 ? Fe1 O2 Fe1 99.86(6) . 2_656 ? C8 O3 Fe1 128.48(14) . 2_656 ? O1 Fe1 O3 105.97(6) . 2_656 ? O1 Fe1 O2 85.85(6) . . ? O3 Fe1 O2 166.12(6) 2_656 . ? O1 Fe1 O2 164.53(6) . 2_656 ? O3 Fe1 O2 87.20(6) 2_656 2_656 ? O2 Fe1 O2 80.14(6) . 2_656 ? O1 Fe1 N1 86.57(7) . . ? O3 Fe1 N1 82.78(7) 2_656 . ? O2 Fe1 N1 90.87(7) . . ? O2 Fe1 N1 87.11(7) 2_656 . ? O1 Fe1 Br1 92.75(5) . . ? O3 Fe1 Br1 87.98(5) 2_656 . ? O2 Fe1 Br1 98.88(5) . . ? O2 Fe1 Br1 95.85(5) 2_656 . ? N1 Fe1 Br1 170.16(5) . . ? 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 C1 O2 1.302(3) . ? C1 C2 1.422(3) . ? C1 C6 1.431(3) . ? C2 C3 1.413(3) . ? C2 C7 1.439(3) . ? C3 C4 1.384(3) . ? C3 H3 0.98(3) . ? C4 C5 1.393(3) . ? C4 C9 1.537(3) . ? C5 C6 1.400(3) . ? C5 H5 0.93(3) . ? C6 C8 1.445(3) . ? C7 O1 1.243(3) . ? C7 H7 0.96(3) . ? C8 O3 1.234(3) . ? C8 H8 0.99(3) . ? C9 C10 1.523(3) . ? C9 C12 1.536(3) . ? C9 C11 1.538(3) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 N1 1.130(3) . ? C13 C14 1.456(4) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 N2 1.137(4) . ? C15 C16 1.453(4) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? N1 Fe1 2.210(2) . ? O1 Fe1 2.0488(16) . ? O2 Fe1 2.1020(15) . ? O2 Fe1 2.1035(15) 2_656 ? O3 Fe1 2.0502(15) 2_656 ? Fe1 Br1 2.6034(4) . ?