#_______________________________________________________________________ # # Requested by: Jessica Y. Wu and Tobias Ritter # Harvard University # Department of Chemistry and Chemical Biology # 12 Oxford Street # Cambridge, MA 02138 # Tel: (617) 496-0750 # Fax: (617) 496-4591 # Email: ritter@chemistry.harvard.edu # # Crystallography by: Douglas M. Ho and Jessica Y. Wu # Harvard University # Department of Chemistry and Chemical Biology # 12 Oxford Street, B05-B06 # Cambridge, MA 02138 # Tel: (617) 495-0787 # Fax: (617) 496-8783 # Email: ho@chemistry.harvard.edu # # Comments: 682618 = FeCl2(C15H16N2) # = Dichloro(6-methyl-2-((\a-methyl)benzyl- # iminomethyl)pyridine-N,N')iron(II) # at 193(2) K # # This compound crystallizes as orange prisms # (from dichloromethane / diethyl ether) in the # orthorhombic space group P2(1)2(1)2(1) (No. 19) # with 8 molecules per unit cell. # # Version date: March 17, 2008 #_______________________________________________________________________ data_682618 _audit_creation_method SHELXL-97 _chemical_name_systematic ; Dichloro(6-methyl-2-((\a-methyl)benzyliminomethyl)pyridine-N,N')iron(II) ; _chemical_name_common 'JYW02157' _chemical_formula_iupac '[Fe Cl2 (C15 H16 N2)]' _chemical_formula_moiety 'C15 H16 Cl2 Fe N2' _chemical_formula_structural '(Fe Cl2 (C15 H16 N2))' _chemical_formula_analytical ? _chemical_formula_sum 'C15 H16 Cl2 Fe N2' _chemical_formula_weight 351.05 _chemical_melting_point '166-169\%C dec.' _chemical_compound_source 'chemical synthesis' 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' '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' _symmetry_cell_setting 'Orthorhombic' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 14.3528(7) _cell_length_b 15.0877(7) _cell_length_c 15.1959(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3290.7(3) _cell_formula_units_Z 8 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 3122 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 17.71 _exptl_crystal_description 'prism' _exptl_crystal_colour 'orange' _exptl_crystal_size_max 0.105 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.035 _exptl_crystal_density_diffrn 1.417 _exptl_crystal_density_method 'not measured' _exptl_crystal_density_meas ? _exptl_crystal_F_000 1440 _exptl_absorpt_coefficient_mu 1.232 _exptl_absorpt_correction_type 'numerical' _exptl_absorpt_correction_T_min 0.8815 _exptl_absorpt_correction_T_max 0.9581 _exptl_absorpt_process_details 'SADABS (Bruker AXS, 2004)' _exptl_special_details ; The compound was crystallized from a dichloromethane / diethyl ether solution as orange prisms. A crystal 0.035 mm x 0.100 mm x 0.105 mm in size was selected, mounted on a nylon loop with Paratone-N oil, and transferred to a Bruker SMART APEX II diffractometer equipped with an Oxford Cryosystems 700 Series Cryostream Cooler and Mo K\a radiation (\l = 0.71073 \%A). A total of 1830 frames were collected at 193(2) K to \q~max~ = 25.00\% with an oscillation range of 0.5\%/frame, and an exposure time of 30 s/frame using the APEX2 suite of software. (Bruker AXS, 2006a) Data were collected to \q~max~ = 25.00\% rather than the routine value of \q~max~ = 27.50\% because the crystal examined did not exhibit usable diffraction beyond 25.00\%. Unit cell refinement on all observed reflections, and data reduction with corrections for Lp and decay were performed using SAINT. (Bruker AXS, 2006b) Scaling and a numerical absorption correction were done using SADABS. (Bruker AXS, 2004) The minimum and maximum transmission factors were 0.8815 and 0.9581, respectively. A total of 45525 reflections were collected, 5793 were unique (R~int~ = 0.1186), and 3820 had I > 2\s(I). Systematic absences were consistent with the compound having crystallized in the orthorhombic space group P2~1~2~1~2~1~. The chiral space group P2~1~2~1~2~1~ (No. 19) was selected based on an observed mean |E^2^-1| value of 0.816 (versus the expectation values of 0.968 and 0.736 for centric and noncentric data, respectively). ________________________________________________________________________ Bruker AXS (2004). SADABS. Bruker Analytical X-ray Systems Inc., Madison, Wisconsin, USA. Bruker AXS (2006a). APEX2 v2.1-0. Bruker Analytical X-ray Systems Inc., Madison, Wisconsin, USA. Bruker AXS (2006b). SAINT V7.34A. Bruker Analytical X-ray Systems Inc., Madison, Wisconsin, USA. ________________________________________________________________________ ; _diffrn_ambient_temperature 193(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'graphite' _diffrn_measurement_device_type 'Bruker APEX II CCD' _diffrn_measurement_method '\w scans, 1830 0.5\% rotations' _diffrn_detector_area_resol_mean 836.6 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 45525 _diffrn_reflns_av_R_equivalents 0.1186 _diffrn_reflns_av_sigmaI/netI 0.0750 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 25.00 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _reflns_number_total 5793 _reflns_number_gt 3820 _reflns_threshold_expression 'I>2\s(I)' _computing_data_collection 'APEX2 v2.1-0 (Bruker AXS, 2006a)' _computing_cell_refinement 'SAINT V7.34A (Bruker AXS, 2006b)' _computing_data_reduction ; SAINT V7.34A (Bruker AXS, 2006b), SADABS (Bruker AXS, 2004) ; _computing_structure_solution 'SHELXTL v6.12 (Bruker AXS, 2001)' _computing_structure_refinement 'SHELXTL v6.12 (Bruker AXS, 2001)' _computing_molecular_graphics 'SHELXTL v6.12 (Bruker AXS, 2001)' _computing_publication_material 'SHELXTL v6.12 (Bruker AXS, 2001)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger. The structure was solved by direct methods and refined by full-matrix least-squares on F^2^ using SHELXTL. (Bruker AXS, 2001) The asymmetric unit was found to contain two molecules of dichloro(6-methyl- 2-((\a-methyl)benzyliminomethyl)pyridine-N,N')iron(II). All of the nonhydrogen atoms were refined with anisotropic displacement coefficients. The hydrogen atoms were assigned isotropic displacement coefficients U(H) = 1.2U(C) or 1.5U(C~methyl~), and their coordinates were allowed to ride on their respective carbons. The 6-methyl-2-((\a-methyl)benzyliminomethyl)pyridine-N,N' ligand bound to Fe(1') was treated with a two-site disorder model consisting of partial atoms with fixed site occupancy factors of a half. The atoms associated with the two sites were specified with a prime or an asterisk, e.g., N(1') and N(1*), and included in the least-squares refinement with rigid-bond and similar U~ij~ restraints. The refinement converged to R(F) = 0.0464, wR(F^2^) = 0.0849, and S = 1.026 for 3820 reflections with I > 2\s(I), and R(F) = 0.0944, wR(F^2^) = 0.1029, and S = 1.026 for 5793 unique reflections, 520 parameters, and 556 restraints. The maximum |\D/\s| in the final cycle of least-squares was 0.001, and the residual peaks on the final difference-Fourier map ranged from -0.348 to 0.376 e\%A^-3^. Scattering factors were taken from the International Tables for Crystallography, Volume C. (Maslen et al., 1992, and Creagh & McAuley, 1992) The Flack absolute structure parameter refined to x = 0.01(3) [versus the expectation values of 0 (within 3 esd's) for correct and +1 for inverted absolute structure] indicating that the coordinates provided below are for the correct hand (i.e., S) of the molecules. (Flack, 1983) ________________________________________________________________________ R(F ) = R1 = \S ||F~o~|-|F~c~|| / \S|F~o~|, wR(F ^2^) = wR2 = [ \S w (F~o~^2^-F~c~^2^)^2^ / \S w (F~o~^2^)^2^ ]^1/2^, and S = Goodness-of-fit on F ^2^ = [ \S w (F~o~^2^-F~c~^2^)^2^ / (n-p) ]^1/2^, where n is the number of reflections and p is the number of parameters refined. ________________________________________________________________________ Bruker AXS (2001). SHELXTL v6.12. Bruker Analytical X-ray Systems Inc., Madison, Wisconsin, USA. Creagh, D. C. & McAuley, W. J. (1992). International Tables for Crystallography: Mathematical, Physical and Chemical Tables, Vol C, edited by A. J. C. Wilson, pp. 206-222. Dordrecht, The Netherlands: Kluwer. Flack, H. D. (1983). Acta Crystallographica, Section A, 39, 876-881. Maslen, E. N., Fox, A. G. & O'Keefe, M. A. (1992). International Tables for Crystallography: Mathematical, Physical and Chemical Tables, Vol C, edited by A. J. C. Wilson, pp. 476-516. Dordrecht, The Netherlands: Kluwer. ________________________________________________________________________ ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0409P)^2^+0.0193P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(3) _chemical_absolute_configuration ad _refine_ls_number_reflns 5793 _refine_ls_number_parameters 520 _refine_ls_number_restraints 556 _refine_ls_R_factor_all 0.0944 _refine_ls_R_factor_gt 0.0464 _refine_ls_wR_factor_ref 0.1029 _refine_ls_wR_factor_gt 0.0849 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 0.985 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.376 _refine_diff_density_min -0.348 _refine_diff_density_rms 0.066 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 0.40279(5) 0.69692(5) 0.54731(5) 0.0420(2) Uani 1 1 d . . . Cl1 Cl 0.30135(15) 0.59433(11) 0.50324(12) 0.0781(6) Uani 1 1 d . . . Cl2 Cl 0.50811(12) 0.76072(12) 0.46026(11) 0.0789(6) Uani 1 1 d . . . N1 N 0.3410(3) 0.7908(3) 0.6317(3) 0.0316(10) Uani 1 1 d . . . C2 C 0.3717(3) 0.7855(3) 0.7150(3) 0.0295(12) Uani 1 1 d . . . C3 C 0.3391(3) 0.8394(3) 0.7811(3) 0.0357(13) Uani 1 1 d . . . H3 H 0.3606 0.8328 0.8399 0.043 Uiso 1 1 calc R . . C4 C 0.2741(4) 0.9035(3) 0.7596(4) 0.0395(15) Uani 1 1 d . . . H4 H 0.2510 0.9426 0.8035 0.047 Uiso 1 1 calc R . . C5 C 0.2437(4) 0.9099(3) 0.6755(4) 0.0385(14) Uani 1 1 d . . . H5 H 0.1987 0.9535 0.6605 0.046 Uiso 1 1 calc R . . C6 C 0.2780(4) 0.8531(3) 0.6110(4) 0.0368(14) Uani 1 1 d . . . C7 C 0.2445(4) 0.8568(4) 0.5175(3) 0.0511(16) Uani 1 1 d . . . H7A H 0.2977 0.8506 0.4775 0.077 Uiso 1 1 calc R . . H7B H 0.2136 0.9137 0.5069 0.077 Uiso 1 1 calc R . . H7C H 0.2003 0.8084 0.5070 0.077 Uiso 1 1 calc R . . C8 C 0.4401(3) 0.7154(3) 0.7309(3) 0.0352(12) Uani 1 1 d . . . H8 H 0.4647 0.7065 0.7882 0.042 Uiso 1 1 calc R . . N9 N 0.4666(3) 0.6664(3) 0.6675(3) 0.0365(10) Uani 1 1 d . . . C10 C 0.5384(4) 0.5959(3) 0.6842(4) 0.0421(14) Uani 1 1 d . . . H10 H 0.5548 0.5703 0.6255 0.051 Uiso 1 1 calc R . . C11 C 0.4955(4) 0.5214(4) 0.7370(4) 0.0388(14) Uani 1 1 d . . . C12 C 0.5107(4) 0.5119(4) 0.8276(4) 0.0477(16) Uani 1 1 d . . . H12 H 0.5514 0.5514 0.8573 0.057 Uiso 1 1 calc R . . C13 C 0.4668(5) 0.4455(4) 0.8734(4) 0.0651(19) Uani 1 1 d . . . H13 H 0.4773 0.4399 0.9348 0.078 Uiso 1 1 calc R . . C14 C 0.4084(5) 0.3876(4) 0.8325(5) 0.0646(19) Uani 1 1 d . . . H14 H 0.3785 0.3423 0.8654 0.078 Uiso 1 1 calc R . . C15 C 0.3928(5) 0.3948(4) 0.7439(5) 0.064(2) Uani 1 1 d . . . H15 H 0.3526 0.3542 0.7150 0.077 Uiso 1 1 calc R . . C16 C 0.4363(4) 0.4620(4) 0.6966(4) 0.0489(16) Uani 1 1 d . . . H16 H 0.4251 0.4671 0.6352 0.059 Uiso 1 1 calc R . . C17 C 0.6270(4) 0.6361(4) 0.7208(5) 0.0695(19) Uani 1 1 d . . . H17A H 0.6499 0.6817 0.6803 0.104 Uiso 1 1 calc R . . H17B H 0.6743 0.5897 0.7274 0.104 Uiso 1 1 calc R . . H17C H 0.6141 0.6628 0.7783 0.104 Uiso 1 1 calc R . . Fe1' Fe 0.58580(5) 0.68162(5) 0.05538(5) 0.0433(2) Uani 1 1 d . . . Cl1' Cl 0.47865(12) 0.73574(11) -0.03726(10) 0.0678(5) Uani 1 1 d . A . Cl2' Cl 0.69098(14) 0.58433(10) 0.00815(10) 0.0696(5) Uani 1 1 d . A . N1' N 0.649(2) 0.7806(19) 0.1188(11) 0.030(2) Uani 0.50 1 d PU A 1 C2' C 0.6351(16) 0.7850(16) 0.2102(18) 0.028(2) Uani 0.50 1 d PU A 1 C3' C 0.6775(13) 0.8429(13) 0.2655(11) 0.033(3) Uani 0.50 1 d PU A 1 H3' H 0.6645 0.8425 0.3268 0.040 Uiso 0.50 1 calc PR A 1 C4' C 0.7391(10) 0.9015(10) 0.2306(10) 0.034(3) Uani 0.50 1 d PU A 1 H4' H 0.7715 0.9422 0.2672 0.040 Uiso 0.50 1 calc PR A 1 C5' C 0.7533(13) 0.9006(13) 0.1422(9) 0.034(3) Uani 0.50 1 d PU A 1 H5' H 0.7958 0.9423 0.1181 0.041 Uiso 0.50 1 calc PR A 1 C6' C 0.7097(15) 0.8429(14) 0.0855(10) 0.032(3) Uani 0.50 1 d PU A 1 C7' C 0.7212(17) 0.8393(16) -0.0116(10) 0.055(4) Uani 0.50 1 d PU A 1 H7D H 0.7238 0.8997 -0.0352 0.082 Uiso 0.50 1 calc PR A 1 H7E H 0.6684 0.8077 -0.0376 0.082 Uiso 0.50 1 calc PR A 1 H7F H 0.7792 0.8081 -0.0259 0.082 Uiso 0.50 1 calc PR A 1 C8' C 0.5680(16) 0.7203(13) 0.2427(18) 0.031(2) Uani 0.50 1 d PU A 1 H8' H 0.5500 0.7208 0.3028 0.037 Uiso 0.50 1 calc PR A 1 N9' N 0.533(2) 0.6630(18) 0.1902(16) 0.033(3) Uani 0.50 1 d PU A 1 C10' C 0.4628(11) 0.5992(10) 0.2258(9) 0.040(2) Uani 0.50 1 d PU A 1 H10' H 0.4310 0.6281 0.2769 0.048 Uiso 0.50 1 calc PR A 1 C11' C 0.509(3) 0.511(3) 0.259(2) 0.039(2) Uani 0.50 1 d PU A 1 C12' C 0.5565(13) 0.4611(13) 0.2008(14) 0.041(3) Uani 0.50 1 d PU A 1 H12' H 0.5562 0.4762 0.1401 0.049 Uiso 0.50 1 calc PR A 1 C13' C 0.6060(12) 0.3871(12) 0.2303(9) 0.040(3) Uani 0.50 1 d PU A 1 H13' H 0.6401 0.3515 0.1900 0.048 Uiso 0.50 1 calc PR A 1 C14' C 0.6048(12) 0.3663(12) 0.3197(11) 0.043(3) Uani 0.50 1 d PU A 1 H14' H 0.6380 0.3157 0.3395 0.052 Uiso 0.50 1 calc PR A 1 C15' C 0.5566(11) 0.4171(11) 0.3806(13) 0.041(3) Uani 0.50 1 d PU A 1 H15' H 0.5541 0.4016 0.4411 0.050 Uiso 0.50 1 calc PR A 1 C16' C 0.5117(13) 0.4930(16) 0.3476(16) 0.041(3) Uani 0.50 1 d PU A 1 H16' H 0.4826 0.5327 0.3875 0.049 Uiso 0.50 1 calc PR A 1 C17' C 0.3889(10) 0.5823(9) 0.1536(9) 0.059(4) Uani 0.50 1 d PU A 1 H17D H 0.3509 0.6356 0.1457 0.089 Uiso 0.50 1 calc PR A 1 H17E H 0.3489 0.5327 0.1712 0.089 Uiso 0.50 1 calc PR A 1 H17F H 0.4202 0.5678 0.0981 0.089 Uiso 0.50 1 calc PR A 1 N1* N 0.650(2) 0.7843(18) 0.1387(11) 0.026(2) Uani 0.50 1 d PU A 2 C2* C 0.6232(17) 0.7744(17) 0.2222(16) 0.028(2) Uani 0.50 1 d PU A 2 C3* C 0.6591(11) 0.8300(12) 0.2869(10) 0.027(3) Uani 0.50 1 d PU A 2 H3* H 0.6386 0.8250 0.3462 0.032 Uiso 0.50 1 calc PR A 2 C4* C 0.7245(11) 0.8919(11) 0.2640(9) 0.030(3) Uani 0.50 1 d PU A 2 H4* H 0.7524 0.9269 0.3087 0.036 Uiso 0.50 1 calc PR A 2 C5* C 0.7510(12) 0.9047(11) 0.1772(9) 0.029(3) Uani 0.50 1 d PU A 2 H5* H 0.7935 0.9498 0.1603 0.035 Uiso 0.50 1 calc PR A 2 C6* C 0.7102(16) 0.8456(15) 0.1148(8) 0.030(3) Uani 0.50 1 d PU A 2 C7* C 0.7356(16) 0.8532(15) 0.0182(10) 0.041(4) Uani 0.50 1 d PU A 2 H7G H 0.7854 0.8971 0.0111 0.062 Uiso 0.50 1 calc PR A 2 H7H H 0.6808 0.8719 -0.0154 0.062 Uiso 0.50 1 calc PR A 2 H7I H 0.7571 0.7955 -0.0034 0.062 Uiso 0.50 1 calc PR A 2 C8* C 0.5556(15) 0.7030(13) 0.2355(19) 0.030(3) Uani 0.50 1 d PU A 2 H8* H 0.5281 0.6961 0.2919 0.036 Uiso 0.50 1 calc PR A 2 N9* N 0.533(2) 0.6514(17) 0.1760(17) 0.034(3) Uani 0.50 1 d PU A 2 C10* C 0.4650(12) 0.5787(10) 0.1960(9) 0.040(2) Uani 0.50 1 d PU A 2 H10* H 0.4129 0.6043 0.2315 0.048 Uiso 0.50 1 calc PR A 2 C11* C 0.512(4) 0.512(3) 0.249(2) 0.038(2) Uani 0.50 1 d PU A 2 C12* C 0.5744(13) 0.4460(13) 0.2140(14) 0.041(3) Uani 0.50 1 d PU A 2 H12* H 0.5901 0.4480 0.1533 0.049 Uiso 0.50 1 calc PR A 2 C13* C 0.6127(12) 0.3797(11) 0.2658(11) 0.045(3) Uani 0.50 1 d PU A 2 H13* H 0.6531 0.3368 0.2407 0.054 Uiso 0.50 1 calc PR A 2 C14* C 0.5915(13) 0.3768(13) 0.3532(10) 0.045(3) Uani 0.50 1 d PU A 2 H14* H 0.6191 0.3330 0.3898 0.054 Uiso 0.50 1 calc PR A 2 C15* C 0.5301(11) 0.4375(12) 0.3885(14) 0.046(3) Uani 0.50 1 d PU A 2 H15* H 0.5150 0.4333 0.4493 0.056 Uiso 0.50 1 calc PR A 2 C16* C 0.4898(14) 0.5037(15) 0.3394(16) 0.043(3) Uani 0.50 1 d PU A 2 H16* H 0.4474 0.5438 0.3662 0.051 Uiso 0.50 1 calc PR A 2 C17* C 0.4252(11) 0.5449(10) 0.1096(9) 0.077(5) Uani 0.50 1 d PU A 2 H17G H 0.3824 0.4957 0.1214 0.115 Uiso 0.50 1 calc PR A 2 H17H H 0.4760 0.5242 0.0718 0.115 Uiso 0.50 1 calc PR A 2 H17I H 0.3915 0.5928 0.0800 0.115 Uiso 0.50 1 calc PR A 2 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 0.0516(5) 0.0462(4) 0.0284(4) -0.0067(4) 0.0001(4) 0.0012(4) Cl1 0.0870(13) 0.0673(11) 0.0801(14) -0.0256(10) -0.0214(10) -0.0115(10) Cl2 0.0932(13) 0.1036(14) 0.0401(10) -0.0056(9) 0.0273(9) -0.0114(10) N1 0.032(2) 0.033(2) 0.030(3) 0.001(2) 0.0029(19) 0.000(2) C2 0.031(3) 0.030(3) 0.028(3) -0.001(2) 0.004(2) -0.001(2) C3 0.041(3) 0.039(3) 0.028(3) 0.001(3) 0.007(2) -0.005(3) C4 0.041(3) 0.030(3) 0.047(4) -0.004(3) 0.013(3) -0.003(3) C5 0.033(3) 0.028(3) 0.055(4) 0.006(3) 0.007(3) 0.001(2) C6 0.037(3) 0.031(3) 0.042(4) 0.009(3) -0.003(3) -0.002(3) C7 0.055(4) 0.054(4) 0.045(4) 0.007(3) -0.015(3) 0.004(3) C8 0.038(3) 0.040(3) 0.027(3) 0.002(3) -0.001(2) 0.003(3) N9 0.043(2) 0.034(2) 0.033(3) 0.002(2) 0.010(2) 0.008(2) C10 0.044(3) 0.037(3) 0.045(4) -0.003(3) 0.007(3) 0.010(3) C11 0.042(3) 0.032(3) 0.043(4) -0.003(3) -0.003(3) 0.013(3) C12 0.059(4) 0.041(4) 0.042(4) -0.009(3) -0.005(3) 0.011(3) C13 0.089(5) 0.048(4) 0.058(5) 0.012(4) 0.013(4) 0.019(4) C14 0.075(5) 0.041(4) 0.077(6) 0.015(4) 0.024(4) 0.011(4) C15 0.068(5) 0.033(3) 0.092(6) 0.002(4) -0.010(4) -0.006(3) C16 0.055(4) 0.047(4) 0.045(4) -0.004(3) -0.008(3) 0.010(3) C17 0.035(3) 0.045(4) 0.128(6) 0.011(4) 0.002(4) 0.011(3) Fe1' 0.0557(5) 0.0431(4) 0.0311(4) -0.0029(4) -0.0067(4) 0.0064(4) Cl1' 0.0876(11) 0.0807(11) 0.0352(9) -0.0110(8) -0.0219(8) 0.0295(9) Cl2' 0.0861(13) 0.0671(11) 0.0554(12) -0.0132(9) 0.0022(9) 0.0266(10) N1' 0.034(4) 0.038(4) 0.020(6) 0.006(5) 0.006(5) 0.005(3) C2' 0.028(5) 0.031(5) 0.025(5) 0.005(4) 0.007(4) 0.004(4) C3' 0.035(6) 0.040(5) 0.024(6) 0.004(5) 0.007(5) -0.001(4) C4' 0.037(5) 0.038(5) 0.025(7) 0.004(6) 0.007(6) -0.001(4) C5' 0.035(4) 0.043(5) 0.025(7) 0.007(6) 0.008(6) 0.000(4) C6' 0.037(4) 0.038(4) 0.020(7) 0.007(6) 0.002(6) 0.008(4) C7' 0.069(10) 0.075(12) 0.019(8) 0.019(8) 0.003(8) -0.015(8) C8' 0.031(5) 0.038(6) 0.022(5) 0.003(4) -0.002(4) 0.001(4) N9' 0.034(4) 0.041(6) 0.025(6) 0.006(4) -0.002(5) -0.003(4) C10' 0.036(4) 0.046(5) 0.037(6) 0.004(4) -0.004(4) -0.008(4) C11' 0.034(4) 0.042(4) 0.040(5) 0.008(4) -0.007(5) -0.012(3) C12' 0.040(6) 0.045(5) 0.037(5) 0.013(4) -0.011(5) -0.008(4) C13' 0.050(5) 0.038(5) 0.033(6) 0.012(5) -0.005(5) -0.008(4) C14' 0.049(5) 0.044(5) 0.036(7) 0.014(5) 0.002(6) -0.007(4) C15' 0.042(7) 0.045(6) 0.038(5) 0.014(5) 0.001(5) -0.006(5) C16' 0.040(6) 0.044(5) 0.039(5) 0.008(4) -0.007(5) -0.008(4) C17' 0.056(8) 0.056(8) 0.065(9) 0.030(6) -0.021(6) -0.025(6) N1* 0.028(4) 0.030(4) 0.019(6) -0.002(5) 0.000(5) 0.000(3) C2* 0.029(5) 0.034(5) 0.020(5) 0.004(4) 0.006(4) 0.006(4) C3* 0.027(5) 0.036(5) 0.017(6) 0.002(4) 0.011(4) 0.000(4) C4* 0.034(5) 0.039(5) 0.017(6) 0.002(5) 0.009(5) 0.000(4) C5* 0.037(5) 0.036(4) 0.016(7) 0.002(6) 0.012(7) -0.007(4) C6* 0.037(4) 0.040(4) 0.014(6) 0.004(6) 0.007(6) 0.004(4) C7* 0.055(8) 0.051(8) 0.018(8) 0.003(7) 0.002(7) -0.006(6) C8* 0.027(5) 0.036(6) 0.028(5) 0.004(5) 0.007(4) -0.002(4) N9* 0.033(4) 0.037(5) 0.033(6) 0.004(4) -0.005(5) -0.001(4) C10* 0.036(4) 0.044(5) 0.040(6) 0.007(4) -0.006(5) -0.011(4) C11* 0.036(4) 0.043(4) 0.036(5) 0.006(4) -0.011(4) -0.010(3) C12* 0.042(5) 0.042(5) 0.038(5) 0.010(4) -0.007(5) -0.008(4) C13* 0.051(5) 0.044(5) 0.040(7) 0.011(6) -0.003(6) -0.006(4) C14* 0.050(6) 0.047(5) 0.038(6) 0.015(6) -0.001(6) -0.010(4) C15* 0.049(7) 0.051(6) 0.040(5) 0.012(4) -0.003(5) -0.006(5) C16* 0.041(6) 0.047(5) 0.040(5) 0.007(4) -0.011(5) -0.013(5) C17* 0.090(10) 0.069(10) 0.072(9) 0.028(7) -0.059(8) -0.037(8) _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 N9 2.094(4) . ? Fe1 N1 2.107(4) . ? Fe1 Cl2 2.2275(18) . ? Fe1 Cl1 2.2280(18) . ? N1 C6 1.341(6) . ? N1 C2 1.344(6) . ? C2 C3 1.375(6) . ? C2 C8 1.463(7) . ? C3 C4 1.383(7) . ? C3 H3 0.9500 . ? C4 C5 1.354(7) . ? C4 H4 0.9500 . ? C5 C6 1.394(7) . ? C5 H5 0.9500 . ? C6 C7 1.501(7) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 N9 1.272(6) . ? C8 H8 0.9500 . ? N9 C10 1.503(6) . ? C10 C11 1.512(8) . ? C10 C17 1.515(7) . ? C10 H10 1.0000 . ? C11 C16 1.380(8) . ? C11 C12 1.400(8) . ? C12 C13 1.373(8) . ? C12 H12 0.9500 . ? C13 C14 1.360(9) . ? C13 H13 0.9500 . ? C14 C15 1.369(8) . ? C14 H14 0.9500 . ? C15 C16 1.391(8) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? Fe1' N1' 2.00(2) . ? Fe1' N9* 2.04(3) . ? Fe1' N9' 2.20(3) . ? Fe1' N1* 2.20(2) . ? Fe1' Cl2' 2.2246(18) . ? Fe1' Cl1' 2.2390(16) . ? N1' C6' 1.38(3) . ? N1' C2' 1.41(3) . ? C2' C3' 1.36(3) . ? C2' C8' 1.46(3) . ? C3' C4' 1.357(19) . ? C3' H3' 0.9500 . ? C4' C5' 1.360(16) . ? C4' H4' 0.9500 . ? C5' C6' 1.37(2) . ? C5' H5' 0.9500 . ? C6' C7' 1.485(18) . ? C7' H7D 0.9800 . ? C7' H7E 0.9800 . ? C7' H7F 0.9800 . ? C8' N9' 1.28(2) . ? C8' H8' 0.9500 . ? N9' C10' 1.50(3) . ? C10' C17' 1.548(17) . ? C10' C11' 1.57(5) . ? C10' H10' 1.0000 . ? C11' C12' 1.35(5) . ? C11' C16' 1.37(3) . ? C12' C13' 1.40(2) . ? C12' H12' 0.9500 . ? C13' C14' 1.394(18) . ? C13' H13' 0.9500 . ? C14' C15' 1.39(2) . ? C14' H14' 0.9500 . ? C15' C16' 1.41(2) . ? C15' H15' 0.9500 . ? C16' H16' 0.9500 . ? C17' H17D 0.9800 . ? C17' H17E 0.9800 . ? C17' H17F 0.9800 . ? N1* C6* 1.32(3) . ? N1* C2* 1.33(2) . ? C2* C3* 1.39(3) . ? C2* C8* 1.46(2) . ? C3* C4* 1.368(19) . ? C3* H3* 0.9500 . ? C4* C5* 1.387(16) . ? C4* H4* 0.9500 . ? C5* C6* 1.43(2) . ? C5* H5* 0.9500 . ? C6* C7* 1.516(18) . ? C7* H7G 0.9800 . ? C7* H7H 0.9800 . ? C7* H7I 0.9800 . ? C8* N9* 1.24(2) . ? C8* H8* 0.9500 . ? N9* C10* 1.50(3) . ? C10* C11* 1.45(5) . ? C10* C17* 1.520(17) . ? C10* H10* 1.0000 . ? C11* C16* 1.42(4) . ? C11* C12* 1.44(5) . ? C12* C13* 1.39(2) . ? C12* H12* 0.9500 . ? C13* C14* 1.363(19) . ? C13* H13* 0.9500 . ? C14* C15* 1.38(2) . ? C14* H14* 0.9500 . ? C15* C16* 1.37(2) . ? C15* H15* 0.9500 . ? C16* H16* 0.9500 . ? C17* H17G 0.9800 . ? C17* H17H 0.9800 . ? C17* H17I 0.9800 . ? 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 N9 Fe1 N1 78.55(16) . . ? N9 Fe1 Cl2 108.44(13) . . ? N1 Fe1 Cl2 110.89(12) . . ? N9 Fe1 Cl1 113.25(13) . . ? N1 Fe1 Cl1 112.02(13) . . ? Cl2 Fe1 Cl1 124.42(8) . . ? C6 N1 C2 119.0(4) . . ? C6 N1 Fe1 127.7(4) . . ? C2 N1 Fe1 113.3(3) . . ? N1 C2 C3 122.8(5) . . ? N1 C2 C8 114.7(4) . . ? C3 C2 C8 122.4(5) . . ? C2 C3 C4 118.1(5) . . ? C2 C3 H3 121.0 . . ? C4 C3 H3 121.0 . . ? C5 C4 C3 119.4(5) . . ? C5 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? C4 C5 C6 120.5(5) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? N1 C6 C5 120.3(5) . . ? N1 C6 C7 117.7(5) . . ? C5 C6 C7 122.0(5) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N9 C8 C2 119.7(5) . . ? N9 C8 H8 120.1 . . ? C2 C8 H8 120.1 . . ? C8 N9 C10 119.2(4) . . ? C8 N9 Fe1 113.7(3) . . ? C10 N9 Fe1 127.1(3) . . ? N9 C10 C11 109.7(4) . . ? N9 C10 C17 110.8(4) . . ? C11 C10 C17 116.4(5) . . ? N9 C10 H10 106.5 . . ? C11 C10 H10 106.5 . . ? C17 C10 H10 106.5 . . ? C16 C11 C12 117.8(6) . . ? C16 C11 C10 119.8(5) . . ? C12 C11 C10 122.3(5) . . ? C13 C12 C11 120.1(6) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C14 C13 C12 121.3(7) . . ? C14 C13 H13 119.4 . . ? C12 C13 H13 119.4 . . ? C13 C14 C15 120.0(6) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C14 C15 C16 119.5(6) . . ? C14 C15 H15 120.2 . . ? C16 C15 H15 120.2 . . ? C11 C16 C15 121.3(6) . . ? C11 C16 H16 119.4 . . ? C15 C16 H16 119.4 . . ? C10 C17 H17A 109.5 . . ? C10 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C10 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N1' Fe1' N9* 84.4(8) . . ? N1' Fe1' N9' 78.6(9) . . ? N9* Fe1' N9' 6.0(12) . . ? N1' Fe1' N1* 6.2(11) . . ? N9* Fe1' N1* 78.2(9) . . ? N9' Fe1' N1* 72.4(8) . . ? N1' Fe1' Cl2' 109.8(9) . . ? N9* Fe1' Cl2' 113.3(9) . . ? N9' Fe1' Cl2' 116.6(8) . . ? N1* Fe1' Cl2' 111.4(8) . . ? N1' Fe1' Cl1' 110.1(9) . . ? N9* Fe1' Cl1' 113.1(10) . . ? N9' Fe1' Cl1' 113.4(9) . . ? N1* Fe1' Cl1' 113.1(8) . . ? Cl2' Fe1' Cl1' 120.26(7) . . ? C6' N1' C2' 115.0(18) . . ? C6' N1' Fe1' 128.4(11) . . ? C2' N1' Fe1' 116.5(18) . . ? C3' C2' N1' 125.3(16) . . ? C3' C2' C8' 121.2(19) . . ? N1' C2' C8' 113(2) . . ? C2' C3' C4' 118.0(14) . . ? C2' C3' H3' 121.0 . . ? C4' C3' H3' 121.0 . . ? C3' C4' C5' 118.5(15) . . ? C3' C4' H4' 120.7 . . ? C5' C4' H4' 120.7 . . ? C4' C5' C6' 123.9(16) . . ? C4' C5' H5' 118.0 . . ? C6' C5' H5' 118.0 . . ? C5' C6' N1' 119.3(13) . . ? C5' C6' C7' 126.5(16) . . ? N1' C6' C7' 114.2(14) . . ? N9' C8' C2' 120(2) . . ? N9' C8' H8' 120.0 . . ? C2' C8' H8' 120.0 . . ? C8' N9' C10' 118.2(19) . . ? C8' N9' Fe1' 111.2(19) . . ? C10' N9' Fe1' 130.5(13) . . ? N9' C10' C17' 108.2(13) . . ? N9' C10' C11' 112(2) . . ? C17' C10' C11' 112.3(19) . . ? N9' C10' H10' 108.0 . . ? C17' C10' H10' 108.0 . . ? C11' C10' H10' 108.0 . . ? C12' C11' C16' 121(4) . . ? C12' C11' C10' 118(2) . . ? C16' C11' C10' 120(3) . . ? C11' C12' C13' 119(2) . . ? C11' C12' H12' 120.3 . . ? C13' C12' H12' 120.3 . . ? C14' C13' C12' 119.0(16) . . ? C14' C13' H13' 120.5 . . ? C12' C13' H13' 120.5 . . ? C15' C14' C13' 122.2(16) . . ? C15' C14' H14' 118.9 . . ? C13' C14' H14' 118.9 . . ? C14' C15' C16' 116.1(17) . . ? C14' C15' H15' 121.9 . . ? C16' C15' H15' 121.9 . . ? C11' C16' C15' 122(3) . . ? C11' C16' H16' 119.2 . . ? C15' C16' H16' 119.2 . . ? C6* N1* C2* 122.1(17) . . ? C6* N1* Fe1' 127.6(11) . . ? C2* N1* Fe1' 110.2(18) . . ? N1* C2* C3* 119.8(17) . . ? N1* C2* C8* 114(2) . . ? C3* C2* C8* 126.3(18) . . ? C4* C3* C2* 119.0(12) . . ? C4* C3* H3* 120.5 . . ? C2* C3* H3* 120.5 . . ? C3* C4* C5* 121.7(14) . . ? C3* C4* H4* 119.2 . . ? C5* C4* H4* 119.2 . . ? C4* C5* C6* 115.6(14) . . ? C4* C5* H5* 122.2 . . ? C6* C5* H5* 122.2 . . ? N1* C6* C5* 121.6(11) . . ? N1* C6* C7* 118.6(15) . . ? C5* C6* C7* 119.8(16) . . ? C6* C7* H7G 109.5 . . ? C6* C7* H7H 109.5 . . ? H7G C7* H7H 109.5 . . ? C6* C7* H7I 109.5 . . ? H7G C7* H7I 109.5 . . ? H7H C7* H7I 109.5 . . ? N9* C8* C2* 122(2) . . ? N9* C8* H8* 118.8 . . ? C2* C8* H8* 118.8 . . ? C8* N9* C10* 119(2) . . ? C8* N9* Fe1' 114.8(19) . . ? C10* N9* Fe1' 126.1(13) . . ? C11* C10* N9* 109(2) . . ? C11* C10* C17* 115(2) . . ? N9* C10* C17* 108.4(13) . . ? C11* C10* H10* 108.3 . . ? N9* C10* H10* 108.3 . . ? C17* C10* H10* 108.3 . . ? C16* C11* C12* 115(3) . . ? C16* C11* C10* 120(4) . . ? C12* C11* C10* 124(2) . . ? C13* C12* C11* 123(2) . . ? C13* C12* H12* 118.7 . . ? C11* C12* H12* 118.7 . . ? C14* C13* C12* 119.2(17) . . ? C14* C13* H13* 120.4 . . ? C12* C13* H13* 120.4 . . ? C13* C14* C15* 120.0(17) . . ? C13* C14* H14* 120.0 . . ? C15* C14* H14* 120.0 . . ? C16* C15* C14* 122.7(18) . . ? C16* C15* H15* 118.7 . . ? C14* C15* H15* 118.7 . . ? C15* C16* C11* 120(3) . . ? C15* C16* H16* 120.0 . . ? C11* C16* H16* 120.0 . . ? C10* C17* H17G 109.5 . . ? C10* C17* H17H 109.5 . . ? H17G C17* H17H 109.5 . . ? C10* C17* H17I 109.5 . . ? H17G C17* H17I 109.5 . . ? H17H C17* H17I 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N9 Fe1 N1 C6 179.6(4) . . . . ? Cl2 Fe1 N1 C6 74.1(4) . . . . ? Cl1 Fe1 N1 C6 -69.7(4) . . . . ? N9 Fe1 N1 C2 0.5(3) . . . . ? Cl2 Fe1 N1 C2 -105.0(3) . . . . ? Cl1 Fe1 N1 C2 111.2(3) . . . . ? C6 N1 C2 C3 2.2(7) . . . . ? Fe1 N1 C2 C3 -178.7(4) . . . . ? C6 N1 C2 C8 179.9(4) . . . . ? Fe1 N1 C2 C8 -0.9(5) . . . . ? N1 C2 C3 C4 -2.1(7) . . . . ? C8 C2 C3 C4 -179.7(5) . . . . ? C2 C3 C4 C5 1.2(7) . . . . ? C3 C4 C5 C6 -0.5(8) . . . . ? C2 N1 C6 C5 -1.3(7) . . . . ? Fe1 N1 C6 C5 179.6(4) . . . . ? C2 N1 C6 C7 -179.5(5) . . . . ? Fe1 N1 C6 C7 1.5(7) . . . . ? C4 C5 C6 N1 0.5(8) . . . . ? C4 C5 C6 C7 178.6(5) . . . . ? N1 C2 C8 N9 0.9(7) . . . . ? C3 C2 C8 N9 178.7(5) . . . . ? C2 C8 N9 C10 178.7(4) . . . . ? C2 C8 N9 Fe1 -0.4(6) . . . . ? N1 Fe1 N9 C8 -0.1(4) . . . . ? Cl2 Fe1 N9 C8 108.4(4) . . . . ? Cl1 Fe1 N9 C8 -109.3(4) . . . . ? N1 Fe1 N9 C10 -179.1(4) . . . . ? Cl2 Fe1 N9 C10 -70.7(4) . . . . ? Cl1 Fe1 N9 C10 71.6(4) . . . . ? C8 N9 C10 C11 71.8(6) . . . . ? Fe1 N9 C10 C11 -109.1(4) . . . . ? C8 N9 C10 C17 -58.0(7) . . . . ? Fe1 N9 C10 C17 121.1(4) . . . . ? N9 C10 C11 C16 75.5(7) . . . . ? C17 C10 C11 C16 -157.8(5) . . . . ? N9 C10 C11 C12 -102.0(6) . . . . ? C17 C10 C11 C12 24.7(8) . . . . ? C16 C11 C12 C13 -0.5(8) . . . . ? C10 C11 C12 C13 177.0(5) . . . . ? C11 C12 C13 C14 0.3(9) . . . . ? C12 C13 C14 C15 0.2(10) . . . . ? C13 C14 C15 C16 -0.6(10) . . . . ? C12 C11 C16 C15 0.1(9) . . . . ? C10 C11 C16 C15 -177.4(5) . . . . ? C14 C15 C16 C11 0.4(10) . . . . ? N9* Fe1' N1' C6' 178(2) . . . . ? N9' Fe1' N1' C6' 180(3) . . . . ? N1* Fe1' N1' C6' 171(18) . . . . ? Cl2' Fe1' N1' C6' 65(2) . . . . ? Cl1' Fe1' N1' C6' -69(2) . . . . ? N9* Fe1' N1' C2' 2(2) . . . . ? N9' Fe1' N1' C2' 4(2) . . . . ? N1* Fe1' N1' C2' -5(14) . . . . ? Cl2' Fe1' N1' C2' -111(2) . . . . ? Cl1' Fe1' N1' C2' 115(2) . . . . ? C6' N1' C2' C3' -2(4) . . . . ? Fe1' N1' C2' C3' 174.8(19) . . . . ? C6' N1' C2' C8' 178(2) . . . . ? Fe1' N1' C2' C8' -6(3) . . . . ? N1' C2' C3' C4' 0(3) . . . . ? C8' C2' C3' C4' -180(2) . . . . ? C2' C3' C4' C5' 2(2) . . . . ? C3' C4' C5' C6' -1(2) . . . . ? C4' C5' C6' N1' -1(3) . . . . ? C4' C5' C6' C7' 179(2) . . . . ? C2' N1' C6' C5' 3(3) . . . . ? Fe1' N1' C6' C5' -174(2) . . . . ? C2' N1' C6' C7' -178(2) . . . . ? Fe1' N1' C6' C7' 6(3) . . . . ? C3' C2' C8' N9' -176(2) . . . . ? N1' C2' C8' N9' 5(3) . . . . ? C2' C8' N9' C10' -179(2) . . . . ? C2' C8' N9' Fe1' -2(3) . . . . ? N1' Fe1' N9' C8' -1(2) . . . . ? N9* Fe1' N9' C8' 163(19) . . . . ? N1* Fe1' N9' C8' 0(2) . . . . ? Cl2' Fe1' N9' C8' 105.5(19) . . . . ? Cl1' Fe1' N9' C8' -108.4(19) . . . . ? N1' Fe1' N9' C10' 175(3) . . . . ? N9* Fe1' N9' C10' -21(15) . . . . ? N1* Fe1' N9' C10' 176(3) . . . . ? Cl2' Fe1' N9' C10' -78(3) . . . . ? Cl1' Fe1' N9' C10' 68(2) . . . . ? C8' N9' C10' C17' 144(2) . . . . ? Fe1' N9' C10' C17' -33(3) . . . . ? C8' N9' C10' C11' -92(3) . . . . ? Fe1' N9' C10' C11' 92(3) . . . . ? N9' C10' C11' C12' -61(4) . . . . ? C17' C10' C11' C12' 61(4) . . . . ? N9' C10' C11' C16' 110(3) . . . . ? C17' C10' C11' C16' -128(3) . . . . ? C16' C11' C12' C13' 3(5) . . . . ? C10' C11' C12' C13' 174(2) . . . . ? C11' C12' C13' C14' 0(3) . . . . ? C12' C13' C14' C15' -1(2) . . . . ? C13' C14' C15' C16' -2(2) . . . . ? C12' C11' C16' C15' -6(6) . . . . ? C10' C11' C16' C15' -177(2) . . . . ? C14' C15' C16' C11' 6(3) . . . . ? N1' Fe1' N1* C6* -10(14) . . . . ? N9* Fe1' N1* C6* 177(2) . . . . ? N9' Fe1' N1* C6* 179(3) . . . . ? Cl2' Fe1' N1* C6* 67(2) . . . . ? Cl1' Fe1' N1* C6* -72(2) . . . . ? N1' Fe1' N1* C2* 173(17) . . . . ? N9* Fe1' N1* C2* 0(2) . . . . ? N9' Fe1' N1* C2* 2(2) . . . . ? Cl2' Fe1' N1* C2* -110.3(19) . . . . ? Cl1' Fe1' N1* C2* 110.6(18) . . . . ? C6* N1* C2* C3* 0(4) . . . . ? Fe1' N1* C2* C3* 177.0(16) . . . . ? C6* N1* C2* C8* 180(2) . . . . ? Fe1' N1* C2* C8* -3(3) . . . . ? N1* C2* C3* C4* -2(3) . . . . ? C8* C2* C3* C4* 178(2) . . . . ? C2* C3* C4* C5* 4(2) . . . . ? C3* C4* C5* C6* -4(2) . . . . ? C2* N1* C6* C5* 1(3) . . . . ? Fe1' N1* C6* C5* -175.9(18) . . . . ? C2* N1* C6* C7* -179(3) . . . . ? Fe1' N1* C6* C7* 4(3) . . . . ? C4* C5* C6* N1* 1(2) . . . . ? C4* C5* C6* C7* -179.1(18) . . . . ? N1* C2* C8* N9* 7(3) . . . . ? C3* C2* C8* N9* -173(2) . . . . ? C2* C8* N9* C10* 179(2) . . . . ? C2* C8* N9* Fe1' -6(3) . . . . ? N1' Fe1' N9* C8* 2(2) . . . . ? N9' Fe1' N9* C8* -13(16) . . . . ? N1* Fe1' N9* C8* 3(2) . . . . ? Cl2' Fe1' N9* C8* 112(2) . . . . ? Cl1' Fe1' N9* C8* -107(2) . . . . ? N1' Fe1' N9* C10* 177(2) . . . . ? N9' Fe1' N9* C10* 161(19) . . . . ? N1* Fe1' N9* C10* 178(3) . . . . ? Cl2' Fe1' N9* C10* -74(2) . . . . ? Cl1' Fe1' N9* C10* 68(2) . . . . ? C8* N9* C10* C11* -73(3) . . . . ? Fe1' N9* C10* C11* 113(3) . . . . ? C8* N9* C10* C17* 162(2) . . . . ? Fe1' N9* C10* C17* -13(3) . . . . ? N9* C10* C11* C16* 108(4) . . . . ? C17* C10* C11* C16* -131(3) . . . . ? N9* C10* C11* C12* -79(4) . . . . ? C17* C10* C11* C12* 43(5) . . . . ? C16* C11* C12* C13* -1(5) . . . . ? C10* C11* C12* C13* -175(3) . . . . ? C11* C12* C13* C14* -1(3) . . . . ? C12* C13* C14* C15* 2(2) . . . . ? C13* C14* C15* C16* -2(3) . . . . ? C14* C15* C16* C11* -1(3) . . . . ? C12* C11* C16* C15* 2(5) . . . . ? C10* C11* C16* C15* 176(3) . . . . ?