#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/85/2228543.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_2228543
loop_
_publ_author_name
'Liu, Shizheng'
'Yang, Jie'
'Lv, Lei'
'Li, Dacheng'
_publ_section_title
;
 Dichlorido{1-[(2-hydroxyethyl)iminomethyl]-2-naphtholato}pyridineiron(III)
 pyridine monosolvate
;
_journal_coeditor_code           RZ2519
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1585
_journal_paper_doi               10.1107/S1600536810046623
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          '[Fe (C13 H12 N O2) Cl2 (C5 H5 N)], C5 H5 N'
_chemical_formula_moiety         'C18 H17 Cl2 Fe N2 O2, C5 H5 N'
_chemical_formula_sum            'C23 H22 Cl2 Fe N3 O2'
_chemical_formula_weight         499.19
_chemical_name_systematic
;
Dichlorido{1-[(2-hydroxyethyl)iminomethyl]-2-naphtholato}pyridineiron(III)
pyridine monosolvate
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.1230(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.8590(6)
_cell_length_b                   10.0153(11)
_cell_length_c                   14.4884(16)
_cell_measurement_reflns_used    3504
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.011
_cell_measurement_theta_min      2.472
_cell_volume                     1140.4(2)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        'SAINT (Siemens, 1996)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_sigmaI/netI    0.0313
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5726
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.41
_exptl_absorpt_coefficient_mu    0.920
_exptl_absorpt_correction_T_max  0.7270
_exptl_absorpt_correction_T_min  0.6664
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Siemens, 1996)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             514
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.37
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.191
_refine_ls_abs_structure_details 'Flack (1983), 1265 Friedel pairs'
_refine_ls_abs_structure_Flack   0.02(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3395
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0320
_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/[σ²(Fo²)+(0.0476P)²+0.5289P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0801
_refine_ls_wR_factor_ref         0.0845
_reflns_number_gt                3143
_reflns_number_total             3395
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            rz2519.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2228543
_cod_database_fobs_code          2228543
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe Fe1 0.54656(5) 0.51232(5) 0.28032(3) 0.03179(13) Uani d . 1 . .
Cl Cl1 0.81839(12) 0.59516(12) 0.27394(7) 0.0505(3) Uani d . 1 . .
Cl Cl2 0.61339(13) 0.29636(11) 0.33678(7) 0.0486(3) Uani d . 1 . .
N N1 0.2862(3) 0.4752(3) 0.30300(17) 0.0321(7) Uani d . 1 . .
N N2 0.4541(4) 0.7190(4) 0.2447(2) 0.0386(7) Uani d . 1 . .
N N3 0.7698(4) 0.5286(4) 0.52783(19) 0.0458(8) Uani d . 1 . .
O O1 0.5126(3) 0.5757(3) 0.41754(15) 0.0374(6) Uani d . 1 . .
H H1 0.5968 0.5524 0.4469 0.056 Uiso d R 1 . .
O O2 0.5074(3) 0.4537(3) 0.15755(16) 0.0386(6) Uani d . 1 . .
C C1 0.3621(4) 0.5234(5) 0.4608(2) 0.0434(9) Uani d . 1 . .
H H1A 0.3330 0.5757 0.5149 0.052 Uiso calc R 1 . .
H H1B 0.3798 0.4315 0.4796 0.052 Uiso calc R 1 . .
C C2 0.2222(4) 0.5320(5) 0.3892(2) 0.0409(10) Uani d . 1 . .
H H2A 0.1231 0.4827 0.4098 0.049 Uiso calc R 1 . .
H H2B 0.1894 0.6244 0.3798 0.049 Uiso calc R 1 . .
C C3 0.1855(4) 0.4104(4) 0.2498(2) 0.0331(8) Uani d . 1 . .
H H3 0.0734 0.4006 0.2690 0.040 Uiso calc R 1 . .
C C4 0.2316(4) 0.3513(4) 0.1627(2) 0.0309(8) Uani d . 1 . .
C C5 0.3927(4) 0.3731(4) 0.1223(2) 0.0334(8) Uani d . 1 . .
C C6 0.4347(5) 0.3075(5) 0.0381(2) 0.0440(10) Uani d . 1 . .
H H6 0.5403 0.3227 0.0113 0.053 Uiso calc R 1 . .
C C7 0.3239(5) 0.2239(5) -0.0032(2) 0.0505(11) Uani d . 1 . .
H H7 0.3564 0.1808 -0.0572 0.061 Uiso calc R 1 . .
C C8 0.1613(5) 0.1997(4) 0.0327(2) 0.0419(10) Uani d . 1 . .
C C9 0.1090(5) 0.2669(4) 0.1152(2) 0.0330(8) Uani d . 1 . .
C C10 -0.0580(5) 0.2445(4) 0.1469(3) 0.0431(9) Uani d . 1 . .
H H10 -0.0968 0.2911 0.1982 0.052 Uiso calc R 1 . .
C C11 -0.1640(6) 0.1561(5) 0.1041(3) 0.0566(12) Uani d . 1 . .
H H11 -0.2733 0.1426 0.1268 0.068 Uiso calc R 1 . .
C C12 -0.1089(6) 0.0855(6) 0.0261(3) 0.0632(14) Uani d . 1 . .
H H12 -0.1796 0.0221 -0.0011 0.076 Uiso calc R 1 . .
C C13 0.0459(6) 0.1095(5) -0.0094(3) 0.0576(12) Uani d . 1 . .
H H13 0.0783 0.0656 -0.0631 0.069 Uiso calc R 1 . .
C C14 0.3280(5) 0.7367(5) 0.1839(3) 0.0496(10) Uani d . 1 . .
H H14 0.2786 0.6622 0.1565 0.060 Uiso calc R 1 . .
C C15 0.2690(7) 0.8615(6) 0.1604(3) 0.0659(14) Uani d . 1 . .
H H15 0.1814 0.8708 0.1177 0.079 Uiso calc R 1 . .
C C16 0.3409(7) 0.9727(5) 0.2009(4) 0.0731(16) Uani d . 1 . .
H H16 0.3043 1.0580 0.1851 0.088 Uiso calc R 1 . .
C C17 0.4661(7) 0.9548(5) 0.2644(4) 0.0635(13) Uani d . 1 . .
H H17 0.5147 1.0279 0.2940 0.076 Uiso calc R 1 . .
C C18 0.5204(5) 0.8271(5) 0.2843(3) 0.0509(10) Uani d . 1 . .
H H18 0.6071 0.8160 0.3274 0.061 Uiso calc R 1 . .
C C19 0.8321(6) 0.4104(5) 0.5477(3) 0.0588(13) Uani d . 1 . .
H H19 0.7821 0.3355 0.5211 0.071 Uiso calc R 1 . .
C C20 0.9701(7) 0.3926(6) 0.6070(4) 0.0650(14) Uani d . 1 . .
H H20 1.0113 0.3077 0.6200 0.078 Uiso calc R 1 . .
C C21 1.0421(5) 0.5014(8) 0.6448(3) 0.0656(14) Uani d . 1 . .
H H21 1.1334 0.4929 0.6852 0.079 Uiso calc R 1 . .
C C22 0.9803(7) 0.6227(7) 0.6233(4) 0.0805(19) Uani d . 1 . .
H H22 1.0306 0.6991 0.6476 0.097 Uiso calc R 1 . .
C C23 0.8438(7) 0.6334(6) 0.5658(4) 0.0663(14) Uani d . 1 . .
H H23 0.8009 0.7178 0.5527 0.080 Uiso calc R 1 . .
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'
O O 0.0106 0.0060 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 Fe1 O1 . . 163.37(10) ?
O2 Fe1 N1 . . 86.33(10) ?
O1 Fe1 N1 . . 77.32(9) ?
O2 Fe1 N2 . . 91.01(11) ?
O1 Fe1 N2 . . 84.14(11) ?
N1 Fe1 N2 . . 83.39(11) ?
O2 Fe1 Cl1 . . 102.90(8) ?
O1 Fe1 Cl1 . . 92.81(7) ?
N1 Fe1 Cl1 . . 167.24(9) ?
N2 Fe1 Cl1 . . 87.61(8) ?
O2 Fe1 Cl2 . . 94.40(9) ?
O1 Fe1 Cl2 . . 88.73(8) ?
N1 Fe1 Cl2 . . 90.00(9) ?
N2 Fe1 Cl2 . . 171.18(9) ?
Cl1 Fe1 Cl2 . . 97.95(4) ?
C3 N1 C2 . . 119.9(3) ?
C3 N1 Fe1 . . 126.5(2) ?
C2 N1 Fe1 . . 113.6(2) ?
C18 N2 C14 . . 117.8(4) ?
C18 N2 Fe1 . . 121.5(3) ?
C14 N2 Fe1 . . 120.7(3) ?
C19 N3 C23 . . 117.5(3) ?
C1 O1 Fe1 . . 114.1(2) ?
C1 O1 H1 . . 109.5 ?
Fe1 O1 H1 . . 107.4 ?
C5 O2 Fe1 . . 131.7(2) ?
O1 C1 C2 . . 106.1(3) ?
O1 C1 H1A . . 110.5 ?
C2 C1 H1A . . 110.5 ?
O1 C1 H1B . . 110.5 ?
C2 C1 H1B . . 110.5 ?
H1A C1 H1B . . 108.7 ?
N1 C2 C1 . . 108.3(3) ?
N1 C2 H2A . . 110.0 ?
C1 C2 H2A . . 110.0 ?
N1 C2 H2B . . 110.0 ?
C1 C2 H2B . . 110.0 ?
H2A C2 H2B . . 108.4 ?
N1 C3 C4 . . 125.4(3) ?
N1 C3 H3 . . 117.3 ?
C4 C3 H3 . . 117.3 ?
C5 C4 C3 . . 121.8(3) ?
C5 C4 C9 . . 119.1(3) ?
C3 C4 C9 . . 119.1(3) ?
O2 C5 C4 . . 123.2(3) ?
O2 C5 C6 . . 117.2(3) ?
C4 C5 C6 . . 119.6(3) ?
C7 C6 C5 . . 121.1(4) ?
C7 C6 H6 . . 119.5 ?
C5 C6 H6 . . 119.5 ?
C6 C7 C8 . . 122.1(4) ?
C6 C7 H7 . . 119.0 ?
C8 C7 H7 . . 119.0 ?
C7 C8 C13 . . 122.2(4) ?
C7 C8 C9 . . 119.5(3) ?
C13 C8 C9 . . 118.3(4) ?
C10 C9 C8 . . 117.8(3) ?
C10 C9 C4 . . 123.7(3) ?
C8 C9 C4 . . 118.5(3) ?
C11 C10 C9 . . 121.6(4) ?
C11 C10 H10 . . 119.2 ?
C9 C10 H10 . . 119.2 ?
C10 C11 C12 . . 120.3(4) ?
C10 C11 H11 . . 119.9 ?
C12 C11 H11 . . 119.9 ?
C13 C12 C11 . . 119.9(4) ?
C13 C12 H12 . . 120.0 ?
C11 C12 H12 . . 120.0 ?
C12 C13 C8 . . 121.9(4) ?
C12 C13 H13 . . 119.0 ?
C8 C13 H13 . . 119.0 ?
N2 C14 C15 . . 122.2(5) ?
N2 C14 H14 . . 118.9 ?
C15 C14 H14 . . 118.9 ?
C14 C15 C16 . . 119.4(4) ?
C14 C15 H15 . . 120.3 ?
C16 C15 H15 . . 120.3 ?
C17 C16 C15 . . 118.5(5) ?
C17 C16 H16 . . 120.7 ?
C15 C16 H16 . . 120.7 ?
C16 C17 C18 . . 119.2(5) ?
C16 C17 H17 . . 120.4 ?
C18 C17 H17 . . 120.4 ?
N2 C18 C17 . . 122.9(4) ?
N2 C18 H18 . . 118.6 ?
C17 C18 H18 . . 118.6 ?
N3 C19 C20 . . 122.7(5) ?
N3 C19 H19 . . 118.7 ?
C20 C19 H19 . . 118.7 ?
C21 C20 C19 . . 118.3(5) ?
C21 C20 H20 . . 120.8 ?
C19 C20 H20 . . 120.8 ?
C20 C21 C22 . . 119.1(4) ?
C20 C21 H21 . . 120.5 ?
C22 C21 H21 . . 120.5 ?
C21 C22 C23 . . 119.8(6) ?
C21 C22 H22 . . 120.1 ?
C23 C22 H22 . . 120.1 ?
N3 C23 C22 . . 122.6(5) ?
N3 C23 H23 . . 118.7 ?
C22 C23 H23 . . 118.7 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Fe1 O2 . 1.897(2) ?
Fe1 O1 . 2.105(2) ?
Fe1 N1 . 2.106(3) ?
Fe1 N2 . 2.254(3) ?
Fe1 Cl1 . 2.2938(10) ?
Fe1 Cl2 . 2.3709(12) ?
N1 C3 . 1.280(4) ?
N1 C2 . 1.462(4) ?
N2 C18 . 1.331(6) ?
N2 C14 . 1.336(5) ?
N3 C19 . 1.312(7) ?
N3 C23 . 1.319(6) ?
O1 C1 . 1.439(4) ?
O1 H1 . 0.8200 ?
O2 C5 . 1.313(4) ?
C1 C2 . 1.513(4) ?
C1 H1A . 0.9700 ?
C1 H1B . 0.9700 ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 C4 . 1.440(5) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.414(5) ?
C4 C9 . 1.455(5) ?
C5 C6 . 1.424(5) ?
C6 C7 . 1.348(6) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.402(6) ?
C7 H7 . 0.9300 ?
C8 C13 . 1.417(6) ?
C8 C9 . 1.433(5) ?
C9 C10 . 1.409(5) ?
C10 C11 . 1.364(6) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.403(7) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.344(7) ?
C12 H12 . 0.9300 ?
C13 H13 . 0.9300 ?
C14 C15 . 1.375(7) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.379(8) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.357(7) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.379(6) ?
C17 H17 . 0.9300 ?
C18 H18 . 0.9300 ?
C19 C20 . 1.393(7) ?
C19 H19 . 0.9300 ?
C20 C21 . 1.344(9) ?
C20 H20 . 0.9300 ?
C21 C22 . 1.345(9) ?
C21 H21 . 0.9300 ?
C22 C23 . 1.361(8) ?
C22 H22 . 0.9300 ?
C23 H23 . 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H1 N3 . 0.82 1.81 2.617(4) 168.0
C12 H12 Cg 2_545 0.93 2.71 3.594(5) 159
C16 H16 Cg 1_565 0.93 2.78 3.653(6) 157
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O2 Fe1 N1 C3 . . . . 12.9(3) ?
O1 Fe1 N1 C3 . . . . -170.2(3) ?
N2 Fe1 N1 C3 . . . . 104.4(3) ?
Cl1 Fe1 N1 C3 . . . . 149.8(3) ?
Cl2 Fe1 N1 C3 . . . . -81.5(3) ?
O2 Fe1 N1 C2 . . . . -167.0(3) ?
O1 Fe1 N1 C2 . . . . 9.8(2) ?
N2 Fe1 N1 C2 . . . . -75.6(3) ?
Cl1 Fe1 N1 C2 . . . . -30.2(5) ?
Cl2 Fe1 N1 C2 . . . . 98.5(3) ?
O2 Fe1 N2 C18 . . . . -146.3(3) ?
O1 Fe1 N2 C18 . . . . 49.6(3) ?
N1 Fe1 N2 C18 . . . . 127.5(3) ?
Cl1 Fe1 N2 C18 . . . . -43.5(3) ?
O2 Fe1 N2 C14 . . . . 34.9(3) ?
O1 Fe1 N2 C14 . . . . -129.1(3) ?
N1 Fe1 N2 C14 . . . . -51.3(3) ?
Cl1 Fe1 N2 C14 . . . . 137.8(3) ?
O2 Fe1 O1 C1 . . . . 29.9(5) ?
N1 Fe1 O1 C1 . . . . 19.0(3) ?
N2 Fe1 O1 C1 . . . . 103.5(3) ?
Cl1 Fe1 O1 C1 . . . . -169.2(3) ?
Cl2 Fe1 O1 C1 . . . . -71.3(3) ?
O1 Fe1 O2 C5 . . . . -36.4(6) ?
N1 Fe1 O2 C5 . . . . -25.7(3) ?
N2 Fe1 O2 C5 . . . . -109.0(3) ?
Cl1 Fe1 O2 C5 . . . . 163.2(3) ?
Cl2 Fe1 O2 C5 . . . . 64.0(3) ?
Fe1 O1 C1 C2 . . . . -42.2(4) ?
C3 N1 C2 C1 . . . . 145.1(4) ?
Fe1 N1 C2 C1 . . . . -34.9(4) ?
O1 C1 C2 N1 . . . . 48.7(5) ?
C2 N1 C3 C4 . . . . 179.1(4) ?
Fe1 N1 C3 C4 . . . . -0.9(5) ?
N1 C3 C4 C5 . . . . -7.3(6) ?
N1 C3 C4 C9 . . . . 172.6(4) ?
Fe1 O2 C5 C4 . . . . 25.9(5) ?
Fe1 O2 C5 C6 . . . . -155.4(3) ?
C3 C4 C5 O2 . . . . -4.1(5) ?
C9 C4 C5 O2 . . . . 176.0(3) ?
C3 C4 C5 C6 . . . . 177.2(3) ?
C9 C4 C5 C6 . . . . -2.8(5) ?
O2 C5 C6 C7 . . . . -179.5(4) ?
C4 C5 C6 C7 . . . . -0.7(6) ?
C5 C6 C7 C8 . . . . 1.7(7) ?
C6 C7 C8 C13 . . . . -178.5(4) ?
C6 C7 C8 C9 . . . . 0.8(7) ?
C7 C8 C9 C10 . . . . 177.3(4) ?
C13 C8 C9 C10 . . . . -3.4(5) ?
C7 C8 C9 C4 . . . . -4.2(5) ?
C13 C8 C9 C4 . . . . 175.1(4) ?
C5 C4 C9 C10 . . . . -176.5(3) ?
C3 C4 C9 C10 . . . . 3.6(5) ?
C5 C4 C9 C8 . . . . 5.1(5) ?
C3 C4 C9 C8 . . . . -174.8(3) ?
C8 C9 C10 C11 . . . . 3.8(6) ?
C4 C9 C10 C11 . . . . -174.6(4) ?
C9 C10 C11 C12 . . . . -0.6(7) ?
C10 C11 C12 C13 . . . . -3.2(8) ?
C11 C12 C13 C8 . . . . 3.5(8) ?
C7 C8 C13 C12 . . . . 179.1(5) ?
C9 C8 C13 C12 . . . . -0.2(7) ?
C18 N2 C14 C15 . . . . 1.4(6) ?
Fe1 N2 C14 C15 . . . . -179.8(3) ?
N2 C14 C15 C16 . . . . -0.3(7) ?
C14 C15 C16 C17 . . . . -1.3(8) ?
C15 C16 C17 C18 . . . . 1.8(8) ?
C14 N2 C18 C17 . . . . -0.9(6) ?
Fe1 N2 C18 C17 . . . . -179.7(3) ?
C16 C17 C18 N2 . . . . -0.7(7) ?
C23 N3 C19 C20 . . . . 0.5(7) ?
N3 C19 C20 C21 . . . . -0.3(8) ?
C19 C20 C21 C22 . . . . -0.8(7) ?
C20 C21 C22 C23 . . . . 1.7(8) ?
C19 N3 C23 C22 . . . . 0.3(8) ?
C21 C22 C23 N3 . . . . -1.5(10) ?
