#_______________________________________________________________________
#
# 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) . . . . ?